#------------------------------------------------------------------------------
#$Date: 2025-07-06 19:44:32 +0200 (Sun 06 de Jul de 2025) $
#$Revision: 301084 $
#$URL: svn://www.crystallography.net/cod/cif/7/16/05/7160564.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7160564
loop_
_publ_author_name
'Chagas, Thaynan A. B.'
'Piscelli, Bruno A.'
'Santos, Hugo'
'Lima, Sâmia R'
'Cormanich, Rodrigo A.'
'Fernandes, Fábio S'
'Coelho, Fernando'
_publ_section_title
;
 An asymmetric and theoretical approach to the Morita-Baylis-Hillman
 reaction using vinyl-1,2,4-oxadiazoles as nucleophiles.
;
_journal_issue                   24
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              5872
_journal_page_last               5881
_journal_paper_doi               10.1039/d5ob00540j
_journal_volume                  23
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H16 N4 O5'
_chemical_formula_structural     C20H16N4O5
_chemical_formula_sum            'C20 H16 N4 O5'
_chemical_formula_weight         392.37
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     'intrinsic phasing'
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2024-10-18 deposited with the CCDC.	2025-05-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.9550(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.6389(4)
_cell_length_b                   14.5769(4)
_cell_length_c                   17.9618(4)
_cell_measurement_reflns_used    9628
_cell_measurement_temperature    301(2)
_cell_measurement_theta_max      71.82
_cell_measurement_theta_min      2.50
_cell_volume                     3775.16(17)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3 (2015)'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics
'Diamond (H. Putz & K. Brandenburg, 2006, v. 4.6.4)'
_computing_publication_material
'SHELXL-2014/7 (Sheldrick, 2015) and WINGX (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT-2015 (Sheldrick 2015a)'
_diffrn_ambient_temperature      301(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 Venture/Photon 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'G\"obbel mirrors'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0756
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            234530
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         71.462
_diffrn_reflns_theta_min         2.497
_diffrn_source                   'muS microsource'
_diffrn_source_type              Incoatec
_exptl_absorpt_coefficient_mu    0.852
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6537
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 - Bruker AXS area detector scaling and absorption correction 
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_description       prism
_exptl_crystal_F_000             1632
_exptl_crystal_size_max          0.309
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.177
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 6229 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1078
_refine_ls_number_reflns         14628
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0393
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0634P)²+0.4512P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0983
_refine_ls_wR_factor_ref         0.1001
_reflns_Friedel_coverage         0.917
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                13826
_reflns_number_total             14628
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5ob00540j2.cif
_cod_data_source_block           shelx
_cod_depositor_comments          'Adding full bibliography for 7160564.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7160564
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.779
_shelx_estimated_absorpt_t_max   0.864
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.0509(2) 0.8659(2) 0.65120(18) 0.0623(7) Uani 1 1 d . . . . .
H1A H -0.061872 0.839705 0.601426 0.094 Uiso 1 1 calc R U . . .
H1B H 0.013212 0.882674 0.664623 0.094 Uiso 1 1 calc R U . . .
H1C H -0.088917 0.919506 0.651947 0.094 Uiso 1 1 calc R U . . .
C2 C -0.07483(18) 0.79696(18) 0.70689(14) 0.0452(5) Uani 1 1 d . . . . .
H2A H -0.028221 0.748983 0.713902 0.054 Uiso 1 1 calc R U . . .
H2B H -0.074105 0.826738 0.755286 0.054 Uiso 1 1 calc R U . . .
N3 N -0.16604(14) 0.75594(14) 0.68158(11) 0.0403(4) Uani 1 1 d . . . . .
C4 C -0.25113(17) 0.79725(17) 0.68828(13) 0.0407(5) Uani 1 1 d . . . . .
C5 C -0.2665(2) 0.87991(19) 0.72206(16) 0.0516(6) Uani 1 1 d . . . . .
H5 H -0.217705 0.917823 0.742973 0.062 Uiso 1 1 calc R U . . .
C6 C -0.3585(2) 0.9038(2) 0.72334(18) 0.0603(7) Uani 1 1 d . . . . .
H6 H -0.370988 0.958804 0.745833 0.072 Uiso 1 1 calc R U . . .
C7 C -0.4313(2) 0.8484(2) 0.69235(18) 0.0598(7) Uani 1 1 d . . . . .
H7 H -0.491926 0.866219 0.694176 0.072 Uiso 1 1 calc R U . . .
C8 C -0.41446(19) 0.7659(2) 0.65827(16) 0.0507(6) Uani 1 1 d . . . . .
H8 H -0.463318 0.728335 0.636759 0.061 Uiso 1 1 calc R U . . .
C9 C -0.32423(17) 0.74090(17) 0.65699(13) 0.0405(5) Uani 1 1 d . . . . .
C10 C -0.28502(17) 0.65436(16) 0.62876(13) 0.0396(5) Uani 1 1 d . . . . .
C11 C -0.17936(17) 0.67480(16) 0.64472(12) 0.0382(5) Uani 1 1 d . . . . .
O12 O -0.11979(12) 0.62339(12) 0.62948(11) 0.0496(4) Uani 1 1 d . . . . .
O13 O -0.30180(14) 0.58110(13) 0.67689(11) 0.0497(4) Uani 1 1 d . . . . .
C14 C -0.3621(3) 0.5544(3) 0.5236(2) 0.0739(10) Uani 1 1 d . . . . .
H14A H -0.379236 0.542063 0.472338 0.089 Uiso 1 1 calc R U . . .
H14B H -0.375913 0.512636 0.559207 0.089 Uiso 1 1 calc R U . . .
C15 C -0.31797(17) 0.63164(18) 0.54609(14) 0.0445(5) Uani 1 1 d . . . . .
C16 C -0.29611(17) 0.69769(18) 0.48997(13) 0.0422(5) Uani 1 1 d . . . . .
N17 N -0.25574(15) 0.77666(15) 0.49896(11) 0.0424(4) Uani 1 1 d . . . . .
C18 C -0.25420(18) 0.80446(19) 0.42594(13) 0.0440(5) Uani 1 1 d . . . . .
N19 N -0.2913(2) 0.7457(2) 0.37497(14) 0.0717(8) Uani 1 1 d . . . . .
O20 O -0.31966(18) 0.67332(16) 0.41720(11) 0.0677(6) Uani 1 1 d . . . . .
C21 C -0.21570(18) 0.89117(19) 0.40485(14) 0.0447(5) Uani 1 1 d . . . . .
C22 C -0.17678(18) 0.9537(2) 0.45967(14) 0.0482(6) Uani 1 1 d . . . . .
H22 H -0.173531 0.939484 0.510523 0.058 Uiso 1 1 calc R U . . .
C23 C -0.14289(19) 1.0368(2) 0.43951(15) 0.0503(6) Uani 1 1 d . . . . .
H23 H -0.117306 1.078901 0.476123 0.060 Uiso 1 1 calc R U . . .
C24 C -0.14794(18) 1.0556(2) 0.36376(15) 0.0489(6) Uani 1 1 d . . . . .
C25 C -0.1847(2) 0.9949(2) 0.30814(15) 0.0600(7) Uani 1 1 d . . . . .
H25 H -0.185594 1.008842 0.257497 0.072 Uiso 1 1 calc R U . . .
C26 C -0.2201(2) 0.9131(2) 0.32851(15) 0.0587(7) Uani 1 1 d . . . . .
H26 H -0.246971 0.872116 0.291395 0.070 Uiso 1 1 calc R U . . .
N27 N -0.11604(19) 1.1454(2) 0.34080(15) 0.0624(6) Uani 1 1 d . . . . .
O28 O -0.1108(2) 1.1558(2) 0.27458(14) 0.1004(11) Uani 1 1 d . . . . .
O29 O -0.0968(2) 1.20369(19) 0.38864(16) 0.0823(7) Uani 1 1 d . . . . .
C30 C -0.2863(3) 0.1549(3) 0.7042(2) 0.0730(9) Uani 1 1 d . . . . .
H30A H -0.333221 0.183360 0.667522 0.109 Uiso 1 1 calc R U . . .
H30B H -0.313335 0.133383 0.745939 0.109 Uiso 1 1 calc R U . . .
H30C H -0.259924 0.104039 0.681270 0.109 Uiso 1 1 calc R U . . .
C31 C -0.2119(2) 0.2232(2) 0.73178(15) 0.0541(6) Uani 1 1 d . . . . .
H31A H -0.238232 0.272444 0.757644 0.065 Uiso 1 1 calc R U . . .
H31B H -0.164262 0.193680 0.768148 0.065 Uiso 1 1 calc R U . . .
N32 N -0.16931(16) 0.26226(15) 0.67133(12) 0.0455(5) Uani 1 1 d . . . . .
C33 C -0.09602(18) 0.22103(17) 0.64177(14) 0.0429(5) Uani 1 1 d . . . . .
C34 C -0.0523(2) 0.13813(19) 0.66242(17) 0.0547(6) Uani 1 1 d . . . . .
H34 H -0.071086 0.100154 0.698530 0.066 Uiso 1 1 calc R U . . .
C35 C 0.0210(2) 0.1149(2) 0.6264(2) 0.0624(8) Uani 1 1 d . . . . .
H35 H 0.051863 0.059675 0.638653 0.075 Uiso 1 1 calc R U . . .
C36 C 0.0493(2) 0.1704(2) 0.5735(2) 0.0631(8) Uani 1 1 d . . . . .
H36 H 0.098959 0.152669 0.550727 0.076 Uiso 1 1 calc R U . . .
C37 C 0.0045(2) 0.25342(19) 0.55333(18) 0.0530(6) Uani 1 1 d . . . . .
H37 H 0.023605 0.291525 0.517424 0.064 Uiso 1 1 calc R U . . .
C38 C -0.06892(18) 0.27743(16) 0.58815(14) 0.0424(5) Uani 1 1 d . . . . .
C39 C -0.12749(18) 0.36297(16) 0.58035(14) 0.0429(5) Uani 1 1 d . . . . .
C40 C -0.19280(18) 0.34386(16) 0.63776(14) 0.0426(5) Uani 1 1 d . . . . .
O41 O -0.25092(15) 0.39697(13) 0.65348(12) 0.0572(5) Uani 1 1 d . . . . .
O42 O -0.06999(15) 0.43851(14) 0.60639(13) 0.0560(5) Uani 1 1 d . . . . .
C43 C -0.1682(3) 0.4530(3) 0.4624(2) 0.0851(12) Uani 1 1 d . . . . .
H43A H -0.200047 0.460303 0.413314 0.102 Uiso 1 1 calc R U . . .
H43B H -0.128076 0.498590 0.484604 0.102 Uiso 1 1 calc R U . . .
C44 C -0.1799(2) 0.37797(18) 0.50061(15) 0.0492(6) Uani 1 1 d . . . . .
C45 C -0.24326(18) 0.3061(2) 0.46559(15) 0.0471(6) Uani 1 1 d . . . . .
N46 N -0.26692(15) 0.23014(16) 0.49422(12) 0.0452(5) Uani 1 1 d . . . . .
C47 C -0.32411(17) 0.1900(2) 0.43391(15) 0.0490(6) Uani 1 1 d . . . . .
N48 N -0.3356(2) 0.2380(2) 0.37223(16) 0.0712(8) Uani 1 1 d . . . . .
O49 O -0.28204(18) 0.31689(17) 0.39254(13) 0.0701(6) Uani 1 1 d . . . . .
C50 C -0.36851(17) 0.0997(2) 0.43614(15) 0.0494(6) Uani 1 1 d . . . . .
C51 C -0.3766(2) 0.0592(3) 0.50413(18) 0.0695(9) Uani 1 1 d . . . . .
H51 H -0.353831 0.089340 0.549155 0.083 Uiso 1 1 calc R U . . .
C52 C -0.4185(2) -0.0260(3) 0.5060(2) 0.0776(11) Uani 1 1 d . . . . .
H52 H -0.424182 -0.053213 0.551768 0.093 Uiso 1 1 calc R U . . .
C53 C -0.4512(2) -0.0689(2) 0.4391(2) 0.0655(8) Uani 1 1 d . . . . .
C54 C -0.4421(2) -0.0319(2) 0.3710(2) 0.0661(8) Uani 1 1 d . . . . .
H54 H -0.463546 -0.063306 0.326352 0.079 Uiso 1 1 calc R U . . .
C55 C -0.4006(2) 0.0530(2) 0.36967(17) 0.0593(7) Uani 1 1 d . . . . .
H55 H -0.394150 0.079014 0.323609 0.071 Uiso 1 1 calc R U . . .
N56 N -0.4981(2) -0.1590(3) 0.4410(3) 0.0913(11) Uani 1 1 d . . . . .
O57 O -0.5120(4) -0.2034(3) 0.3840(4) 0.160(2) Uani 1 1 d . . . . .
O58 O -0.5232(4) -0.1809(4) 0.4981(3) 0.173(3) Uani 1 1 d . . . . .
C59 C 1.1140(3) -0.0615(3) 1.1638(2) 0.0745(9) Uani 1 1 d . . . . .
H59A H 1.077143 -0.094036 1.122803 0.112 Uiso 1 1 calc R U . . .
H59B H 1.142364 -0.104503 1.201306 0.112 Uiso 1 1 calc R U . . .
H59C H 1.161365 -0.027269 1.145194 0.112 Uiso 1 1 calc R U . . .
C60 C 1.05366(18) 0.0027(2) 1.19831(14) 0.0480(6) Uani 1 1 d . . . . .
H60A H 1.007358 -0.032411 1.218672 0.058 Uiso 1 1 calc R U . . .
H60B H 1.091181 0.035150 1.239864 0.058 Uiso 1 1 calc R U . . .
N61 N 1.00723(13) 0.06913(14) 1.14399(10) 0.0381(4) Uani 1 1 d . . . . .
C62 C 1.04817(15) 0.14857(16) 1.11982(12) 0.0362(5) Uani 1 1 d . . . . .
C63 C 1.13866(17) 0.17917(19) 1.14027(15) 0.0452(5) Uani 1 1 d . . . . .
H63 H 1.181919 0.146641 1.174261 0.054 Uiso 1 1 calc R U . . .
C64 C 1.16198(19) 0.2603(2) 1.10793(17) 0.0533(7) Uani 1 1 d . . . . .
H64 H 1.222183 0.282520 1.120823 0.064 Uiso 1 1 calc R U . . .
C65 C 1.0988(2) 0.30886(19) 1.05736(19) 0.0543(7) Uani 1 1 d . . . . .
H65 H 1.116515 0.363303 1.036883 0.065 Uiso 1 1 calc R U . . .
C66 C 1.00830(19) 0.27658(18) 1.03674(17) 0.0491(6) Uani 1 1 d . . . . .
H66 H 0.965300 0.308420 1.002018 0.059 Uiso 1 1 calc R U . . .
C67 C 0.98411(15) 0.19662(16) 1.06894(14) 0.0390(5) Uani 1 1 d . . . . .
C68 C 0.89233(15) 0.14621(17) 1.05865(14) 0.0406(5) Uani 1 1 d . . . . .
C69 C 0.91881(15) 0.06016(16) 1.10816(13) 0.0372(5) Uani 1 1 d . . . . .
O70 O 0.86660(11) -0.00343(13) 1.11555(11) 0.0504(4) Uani 1 1 d . . . . .
O71 O 0.82931(13) 0.19913(14) 1.09189(13) 0.0555(5) Uani 1 1 d . . . . .
C72 C 0.7693(2) 0.1478(3) 0.9448(2) 0.0813(11) Uani 1 1 d . . . . .
H72A H 0.747511 0.133128 0.894492 0.098 Uiso 1 1 calc R U . . .
H72B H 0.731994 0.180786 0.972252 0.098 Uiso 1 1 calc R U . . .
C73 C 0.85314(17) 0.1218(2) 0.97734(16) 0.0488(6) Uani 1 1 d . . . . .
C74 C 0.91289(18) 0.06999(18) 0.93548(14) 0.0476(6) Uani 1 1 d . . . . .
N75 N 0.99588(15) 0.03828(15) 0.95877(11) 0.0442(5) Uani 1 1 d . . . . .
C76 C 1.0187(2) 0.0004(2) 0.89436(14) 0.0521(6) Uani 1 1 d . . . . .
N77 N 0.9535(2) 0.0058(2) 0.83531(14) 0.0720(8) Uani 1 1 d . . . . .
O78 O 0.88188(17) 0.05186(18) 0.86216(11) 0.0701(6) Uani 1 1 d . . . . .
C79 C 1.1097(2) -0.0411(2) 0.89179(18) 0.0582(7) Uani 1 1 d . . . . .
C80 C 1.1728(2) -0.0559(2) 0.9573(2) 0.0644(8) Uani 1 1 d . . . . .
H80 H 1.156768 -0.041157 1.003729 0.077 Uiso 1 1 calc R U . . .
C81 C 1.2596(3) -0.0925(3) 0.9549(3) 0.0856(12) Uani 1 1 d . . . . .
H81 H 1.301757 -0.103140 0.999011 0.103 Uiso 1 1 calc R U . . .
C82 C 1.2813(3) -0.1124(3) 0.8859(4) 0.0984(17) Uani 1 1 d . . . . .
C83 C 1.2210(5) -0.1011(4) 0.8209(4) 0.116(2) Uani 1 1 d . . . . .
H83 H 1.237504 -0.117632 0.775015 0.140 Uiso 1 1 calc R U . . .
C84 C 1.1346(4) -0.0647(3) 0.8232(2) 0.0903(13) Uani 1 1 d . . . . .
H84 H 1.092791 -0.055887 0.778516 0.108 Uiso 1 1 calc R U . . .
N85A N 1.3714(7) -0.1433(5) 0.8747(8) 0.115(4) Uani 0.74(2) 1 d D . P A 1
O86A O 1.3899(9) -0.1446(5) 0.8085(9) 0.164(5) Uani 0.74(2) 1 d D . P A 1
O87A O 1.4237(5) -0.1677(9) 0.9320(10) 0.174(7) Uani 0.74(2) 1 d D . P A 1
N85B N 1.3850(14) -0.1585(14) 0.9105(10) 0.067(5) Uiso 0.26(2) 1 d D . P A 2
O86B O 1.4212(12) -0.1463(11) 0.8551(10) 0.085(5) Uiso 0.26(2) 1 d . . P A 2
O87B O 1.4140(19) -0.1991(17) 0.9614(12) 0.107(8) Uiso 0.26(2) 1 d D . P A 2
C88 C 0.4160(2) 0.2021(3) 1.1331(2) 0.0715(9) Uani 1 1 d . . . . .
H88A H 0.434183 0.217781 1.085845 0.107 Uiso 1 1 calc R U . . .
H88B H 0.397068 0.256621 1.156354 0.107 Uiso 1 1 calc R U . . .
H88C H 0.365252 0.159547 1.124323 0.107 Uiso 1 1 calc R U . . .
C89 C 0.4968(2) 0.1590(2) 1.18459(16) 0.0595(7) Uani 1 1 d . . . . .
H89A H 0.547340 0.202764 1.194123 0.071 Uiso 1 1 calc R U . . .
H89B H 0.478399 0.144522 1.232608 0.071 Uiso 1 1 calc R U . . .
N90 N 0.52929(14) 0.07565(17) 1.15282(12) 0.0464(5) Uani 1 1 d . . . . .
C91 C 0.48485(17) -0.0097(2) 1.15182(16) 0.0521(6) Uani 1 1 d . . . . .
C92 C 0.4081(2) -0.0306(3) 1.1834(3) 0.0876(13) Uani 1 1 d . . . . .
H92 H 0.376620 0.013790 1.206255 0.105 Uiso 1 1 calc R U . . .
C93 C 0.3807(3) -0.1213(4) 1.1791(4) 0.131(2) Uani 1 1 d . . . . .
H93 H 0.329067 -0.138379 1.199548 0.157 Uiso 1 1 calc R U . . .
C94 C 0.4269(3) -0.1868(4) 1.1459(5) 0.131(3) Uani 1 1 d . . . . .
H94 H 0.406916 -0.247406 1.145007 0.158 Uiso 1 1 calc R U . . .
C95 C 0.5039(2) -0.1638(2) 1.1134(3) 0.0857(13) Uani 1 1 d . . . . .
H95 H 0.535039 -0.208080 1.090074 0.103 Uiso 1 1 calc R U . . .
C96 C 0.53189(17) -0.0748(2) 1.11685(17) 0.0507(6) Uani 1 1 d . . . . .
C97 C 0.61507(15) -0.02995(17) 1.09311(14) 0.0396(5) Uani 1 1 d . . . . .
C98 C 0.60447(15) 0.07039(18) 1.11882(13) 0.0404(5) Uani 1 1 d . . . . .
O99 O 0.65767(13) 0.13261(14) 1.11249(14) 0.0599(5) Uani 1 1 d . . . . .
O100 O 0.69606(12) -0.06823(14) 1.13660(11) 0.0491(4) Uani 1 1 d . . . . .
C101 C 0.6799(2) -0.0866(3) 0.9823(2) 0.0718(10) Uani 1 1 d . . . . .
H10A H 0.678776 -0.089647 0.930437 0.086 Uiso 1 1 calc R U . . .
H10B H 0.724514 -0.118995 1.015157 0.086 Uiso 1 1 calc R U . . .
C102 C 0.61802(17) -0.03643(18) 1.00927(15) 0.0453(5) Uani 1 1 d . . . . .
C103 C 0.54804(17) 0.01420(19) 0.95646(14) 0.0446(5) Uani 1 1 d . . . . .
N104 N 0.47097(14) 0.05014(15) 0.96702(11) 0.0446(5) Uani 1 1 d . . . . .
C105 C 0.43470(18) 0.08430(19) 0.89652(14) 0.0459(5) Uani 1 1 d . . . . .
N106 N 0.4865(2) 0.0718(2) 0.84598(15) 0.0716(8) Uani 1 1 d . . . . .
O107 O 0.56401(16) 0.02465(19) 0.88559(12) 0.0700(6) Uani 1 1 d . . . . .
C108 C 0.34328(18) 0.12923(18) 0.87829(14) 0.0445(5) Uani 1 1 d . . . . .
C109 C 0.28888(19) 0.1404(2) 0.93357(14) 0.0482(6) Uani 1 1 d . . . . .
H109 H 0.311444 0.121626 0.982807 0.058 Uiso 1 1 calc R U . . .
C110 C 0.2017(2) 0.1789(2) 0.91657(15) 0.0505(6) Uani 1 1 d . . . . .
H110 H 0.164763 0.185530 0.953446 0.061 Uiso 1 1 calc R U . . .
C111 C 0.17105(18) 0.20728(17) 0.84335(15) 0.0456(5) Uani 1 1 d . . . . .
C112 C 0.2232(2) 0.1979(2) 0.78721(15) 0.0539(6) Uani 1 1 d . . . . .
H112 H 0.200853 0.218258 0.738405 0.065 Uiso 1 1 calc R U . . .
C113 C 0.3094(2) 0.1577(2) 0.80465(15) 0.0561(7) Uani 1 1 d . . . . .
H113 H 0.345131 0.149473 0.767095 0.067 Uiso 1 1 calc R U . . .
N114 N 0.07816(18) 0.24883(18) 0.82422(14) 0.0561(6) Uani 1 1 d . . . . .
O115 O 0.06307(18) 0.29883(18) 0.76915(13) 0.0735(6) Uani 1 1 d . . . . .
O116 O 0.02071(18) 0.2298(3) 0.86335(17) 0.0911(9) Uani 1 1 d . . . . .
H13 H -0.277(3) 0.534(3) 0.663(2) 0.079(12) Uiso 1 1 d . . . . .
H42 H -0.109(2) 0.484(3) 0.608(2) 0.061(9) Uiso 1 1 d . . . . .
H71 H 0.781(3) 0.158(3) 1.097(2) 0.090(13) Uiso 1 1 d . . . . .
H100 H 0.737(3) -0.047(3) 1.118(2) 0.063(10) Uiso 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N3 C2 C1 111.8(2) . . ?
N3 C2 H2A 109.2 . . ?
C1 C2 H2A 109.2 . . ?
N3 C2 H2B 109.2 . . ?
C1 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
C11 N3 C4 111.2(2) . . ?
C11 N3 C2 123.8(2) . . ?
C4 N3 C2 124.9(2) . . ?
C5 C4 C9 121.3(2) . . ?
C5 C4 N3 128.6(2) . . ?
C9 C4 N3 110.1(2) . . ?
C4 C5 C6 117.1(3) . . ?
C4 C5 H5 121.5 . . ?
C6 C5 H5 121.5 . . ?
C7 C6 C5 122.0(3) . . ?
C7 C6 H6 119.0 . . ?
C5 C6 H6 119.0 . . ?
C6 C7 C8 120.1(3) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C9 C8 C7 118.7(3) . . ?
C9 C8 H8 120.6 . . ?
C7 C8 H8 120.6 . . ?
C8 C9 C4 120.8(3) . . ?
C8 C9 C10 130.5(2) . . ?
C4 C9 C10 108.6(2) . . ?
O13 C10 C9 107.92(18) . . ?
O13 C10 C15 111.9(2) . . ?
C9 C10 C15 115.9(2) . . ?
O13 C10 C11 107.65(19) . . ?
C9 C10 C11 101.66(19) . . ?
C15 C10 C11 111.15(19) . . ?
O12 C11 N3 126.9(2) . . ?
O12 C11 C10 124.8(2) . . ?
N3 C11 C10 108.2(2) . . ?
C10 O13 H13 108(3) . . ?
C15 C14 H14A 120.0 . . ?
C15 C14 H14B 120.0 . . ?
H14A C14 H14B 120.0 . . ?
C14 C15 C16 120.0(3) . . ?
C14 C15 C10 122.6(3) . . ?
C16 C15 C10 117.3(2) . . ?
N17 C16 O20 113.1(2) . . ?
N17 C16 C15 130.4(2) . . ?
O20 C16 C15 116.5(2) . . ?
C16 N17 C18 103.1(2) . . ?
N19 C18 N17 113.8(2) . . ?
N19 C18 C21 121.3(2) . . ?
N17 C18 C21 124.9(2) . . ?
C18 N19 O20 103.9(2) . . ?
C16 O20 N19 106.1(2) . . ?
C22 C21 C26 119.2(3) . . ?
C22 C21 C18 120.9(2) . . ?
C26 C21 C18 119.8(2) . . ?
C23 C22 C21 120.8(2) . . ?
C23 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
C24 C23 C22 118.3(3) . . ?
C24 C23 H23 120.9 . . ?
C22 C23 H23 120.9 . . ?
C25 C24 C23 122.5(3) . . ?
C25 C24 N27 118.2(2) . . ?
C23 C24 N27 119.3(3) . . ?
C24 C25 C26 118.9(2) . . ?
C24 C25 H25 120.5 . . ?
C26 C25 H25 120.5 . . ?
C25 C26 C21 120.2(3) . . ?
C25 C26 H26 119.9 . . ?
C21 C26 H26 119.9 . . ?
O29 N27 O28 124.2(3) . . ?
O29 N27 C24 118.2(2) . . ?
O28 N27 C24 117.5(3) . . ?
C31 C30 H30A 109.5 . . ?
C31 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C31 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
N32 C31 C30 113.2(2) . . ?
N32 C31 H31A 108.9 . . ?
C30 C31 H31A 108.9 . . ?
N32 C31 H31B 108.9 . . ?
C30 C31 H31B 108.9 . . ?
H31A C31 H31B 107.8 . . ?
C40 N32 C33 111.0(2) . . ?
C40 N32 C31 124.6(2) . . ?
C33 N32 C31 124.4(2) . . ?
C38 C33 C34 122.1(2) . . ?
C38 C33 N32 109.8(2) . . ?
C34 C33 N32 128.0(2) . . ?
C35 C34 C33 116.5(3) . . ?
C35 C34 H34 121.7 . . ?
C33 C34 H34 121.7 . . ?
C36 C35 C34 122.1(3) . . ?
C36 C35 H35 119.0 . . ?
C34 C35 H35 119.0 . . ?
C35 C36 C37 120.6(3) . . ?
C35 C36 H36 119.7 . . ?
C37 C36 H36 119.7 . . ?
C38 C37 C36 118.1(3) . . ?
C38 C37 H37 120.9 . . ?
C36 C37 H37 120.9 . . ?
C33 C38 C37 120.5(2) . . ?
C33 C38 C39 109.4(2) . . ?
C37 C38 C39 130.1(2) . . ?
O42 C39 C38 108.5(2) . . ?
O42 C39 C44 112.0(2) . . ?
C38 C39 C44 113.2(2) . . ?
O42 C39 C40 108.7(2) . . ?
C38 C39 C40 101.33(19) . . ?
C44 C39 C40 112.6(2) . . ?
O41 C40 N32 126.1(2) . . ?
O41 C40 C39 125.2(2) . . ?
N32 C40 C39 108.5(2) . . ?
C39 O42 H42 104(2) . . ?
C44 C43 H43A 120.0 . . ?
C44 C43 H43B 120.0 . . ?
H43A C43 H43B 120.0 . . ?
C43 C44 C45 120.0(3) . . ?
C43 C44 C39 121.3(3) . . ?
C45 C44 C39 118.7(2) . . ?
N46 C45 O49 113.0(2) . . ?
N46 C45 C44 129.4(2) . . ?
O49 C45 C44 117.6(2) . . ?
C45 N46 C47 102.6(2) . . ?
N48 C47 N46 114.4(3) . . ?
N48 C47 C50 120.9(3) . . ?
N46 C47 C50 124.7(2) . . ?
C47 N48 O49 103.7(2) . . ?
C45 O49 N48 106.2(2) . . ?
C51 C50 C55 119.0(3) . . ?
C51 C50 C47 120.8(3) . . ?
C55 C50 C47 120.2(3) . . ?
C50 C51 C52 120.6(3) . . ?
C50 C51 H51 119.7 . . ?
C52 C51 H51 119.7 . . ?
C53 C52 C51 118.6(3) . . ?
C53 C52 H52 120.7 . . ?
C51 C52 H52 120.7 . . ?
C54 C53 C52 122.3(3) . . ?
C54 C53 N56 119.2(4) . . ?
C52 C53 N56 118.6(4) . . ?
C53 C54 C55 118.8(3) . . ?
C53 C54 H54 120.6 . . ?
C55 C54 H54 120.6 . . ?
C54 C55 C50 120.7(3) . . ?
C54 C55 H55 119.7 . . ?
C50 C55 H55 119.7 . . ?
O58 N56 O57 123.9(5) . . ?
O58 N56 C53 118.0(5) . . ?
O57 N56 C53 118.0(4) . . ?
C60 C59 H59A 109.5 . . ?
C60 C59 H59B 109.5 . . ?
H59A C59 H59B 109.5 . . ?
C60 C59 H59C 109.5 . . ?
H59A C59 H59C 109.5 . . ?
H59B C59 H59C 109.5 . . ?
N61 C60 C59 112.3(2) . . ?
N61 C60 H60A 109.1 . . ?
C59 C60 H60A 109.1 . . ?
N61 C60 H60B 109.1 . . ?
C59 C60 H60B 109.1 . . ?
H60A C60 H60B 107.9 . . ?
C69 N61 C62 110.95(19) . . ?
C69 N61 C60 123.6(2) . . ?
C62 N61 C60 125.42(19) . . ?
C67 C62 C63 121.4(2) . . ?
C67 C62 N61 110.17(19) . . ?
C63 C62 N61 128.5(2) . . ?
C64 C63 C62 117.2(3) . . ?
C64 C63 H63 121.4 . . ?
C62 C63 H63 121.4 . . ?
C65 C64 C63 122.0(2) . . ?
C65 C64 H64 119.0 . . ?
C63 C64 H64 119.0 . . ?
C64 C65 C66 120.1(3) . . ?
C64 C65 H65 120.0 . . ?
C66 C65 H65 120.0 . . ?
C67 C66 C65 118.5(3) . . ?
C67 C66 H66 120.8 . . ?
C65 C66 H66 120.8 . . ?
C66 C67 C62 120.9(2) . . ?
C66 C67 C68 130.4(2) . . ?
C62 C67 C68 108.7(2) . . ?
O71 C68 C67 108.3(2) . . ?
O71 C68 C73 111.7(2) . . ?
C67 C68 C73 114.3(2) . . ?
O71 C68 C69 108.47(19) . . ?
C67 C68 C69 101.20(18) . . ?
C73 C68 C69 112.3(2) . . ?
O70 C69 N61 126.0(2) . . ?
O70 C69 C68 125.3(2) . . ?
N61 C69 C68 108.67(19) . . ?
C68 O71 H71 105(3) . . ?
C73 C72 H72A 120.0 . . ?
C73 C72 H72B 120.0 . . ?
H72A C72 H72B 120.0 . . ?
C72 C73 C74 121.0(3) . . ?
C72 C73 C68 121.8(3) . . ?
C74 C73 C68 117.2(2) . . ?
N75 C74 O78 112.6(3) . . ?
N75 C74 C73 128.9(2) . . ?
O78 C74 C73 118.4(2) . . ?
C74 N75 C76 102.8(2) . . ?
N77 C76 N75 114.3(3) . . ?
N77 C76 C79 122.7(3) . . ?
N75 C76 C79 123.0(2) . . ?
C76 N77 O78 103.6(2) . . ?
C74 O78 N77 106.6(2) . . ?
C80 C79 C84 118.6(4) . . ?
C80 C79 C76 120.9(3) . . ?
C84 C79 C76 120.5(3) . . ?
C79 C80 C81 121.0(4) . . ?
C79 C80 H80 119.5 . . ?
C81 C80 H80 119.5 . . ?
C82 C81 C80 118.1(5) . . ?
C82 C81 H81 121.0 . . ?
C80 C81 H81 121.0 . . ?
C83 C82 C81 122.8(4) . . ?
C83 C82 N85A 113.3(8) . . ?
C81 C82 N85A 123.9(8) . . ?
C83 C82 N85B 135.8(8) . . ?
C81 C82 N85B 101.1(8) . . ?
C82 C83 C84 119.3(4) . . ?
C82 C83 H83 120.4 . . ?
C84 C83 H83 120.4 . . ?
C83 C84 C79 120.3(5) . . ?
C83 C84 H84 119.8 . . ?
C79 C84 H84 119.8 . . ?
O87A N85A O86A 125.5(10) . . ?
O87A N85A C82 115.4(9) . . ?
O86A N85A C82 119.1(11) . . ?
O87B N85B O86B 126(2) . . ?
O87B N85B C82 130(2) . . ?
O86B N85B C82 103.4(13) . . ?
C89 C88 H88A 109.5 . . ?
C89 C88 H88B 109.5 . . ?
H88A C88 H88B 109.5 . . ?
C89 C88 H88C 109.5 . . ?
H88A C88 H88C 109.5 . . ?
H88B C88 H88C 109.5 . . ?
N90 C89 C88 112.5(2) . . ?
N90 C89 H89A 109.1 . . ?
C88 C89 H89A 109.1 . . ?
N90 C89 H89B 109.1 . . ?
C88 C89 H89B 109.1 . . ?
H89A C89 H89B 107.8 . . ?
C98 N90 C91 110.9(2) . . ?
C98 N90 C89 124.9(2) . . ?
C91 N90 C89 124.2(2) . . ?
C92 C91 C96 122.7(3) . . ?
C92 C91 N90 126.9(3) . . ?
C96 C91 N90 110.3(2) . . ?
C91 C92 C93 116.0(4) . . ?
C91 C92 H92 122.0 . . ?
C93 C92 H92 122.0 . . ?
C94 C93 C92 122.3(4) . . ?
C94 C93 H93 118.9 . . ?
C92 C93 H93 118.9 . . ?
C93 C94 C95 120.8(4) . . ?
C93 C94 H94 119.6 . . ?
C95 C94 H94 119.6 . . ?
C96 C95 C94 117.9(4) . . ?
C96 C95 H95 121.0 . . ?
C94 C95 H95 121.0 . . ?
C95 C96 C91 120.3(3) . . ?
C95 C96 C97 130.7(3) . . ?
C91 C96 C97 108.7(2) . . ?
O100 C97 C96 108.3(2) . . ?
O100 C97 C102 110.98(19) . . ?
C96 C97 C102 114.6(2) . . ?
O100 C97 C98 108.96(19) . . ?
C96 C97 C98 101.38(19) . . ?
C102 C97 C98 112.1(2) . . ?
O99 C98 N90 125.9(2) . . ?
O99 C98 C97 125.3(2) . . ?
N90 C98 C97 108.7(2) . . ?
C97 O100 H100 104(3) . . ?
C102 C101 H10A 120.0 . . ?
C102 C101 H10B 120.0 . . ?
H10A C101 H10B 120.0 . . ?
C101 C102 C103 119.2(3) . . ?
C101 C102 C97 122.6(3) . . ?
C103 C102 C97 118.3(2) . . ?
N104 C103 O107 113.2(2) . . ?
N104 C103 C102 129.8(2) . . ?
O107 C103 C102 116.9(2) . . ?
C103 N104 C105 102.7(2) . . ?
N106 C105 N104 114.5(2) . . ?
N106 C105 C108 121.8(2) . . ?
N104 C105 C108 123.7(2) . . ?
C105 N106 O107 103.5(2) . . ?
C103 O107 N106 106.1(2) . . ?
C109 C108 C113 119.4(2) . . ?
C109 C108 C105 120.3(2) . . ?
C113 C108 C105 120.2(2) . . ?
C110 C109 C108 120.9(2) . . ?
C110 C109 H109 119.6 . . ?
C108 C109 H109 119.6 . . ?
C111 C110 C109 118.0(2) . . ?
C111 C110 H110 121.0 . . ?
C109 C110 H110 121.0 . . ?
C112 C111 C110 122.7(2) . . ?
C112 C111 N114 118.6(2) . . ?
C110 C111 N114 118.8(2) . . ?
C111 C112 C113 118.7(2) . . ?
C111 C112 H112 120.7 . . ?
C113 C112 H112 120.7 . . ?
C112 C113 C108 120.3(3) . . ?
C112 C113 H113 119.9 . . ?
C108 C113 H113 119.9 . . ?
O116 N114 O115 124.0(3) . . ?
O116 N114 C111 118.3(2) . . ?
O115 N114 C111 117.7(3) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.501(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 N3 1.462(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
N3 C11 1.353(3) . ?
N3 C4 1.407(3) . ?
C4 C5 1.385(4) . ?
C4 C9 1.388(4) . ?
C5 C6 1.395(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.376(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.392(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.374(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.510(4) . ?
C10 O13 1.422(3) . ?
C10 C15 1.516(3) . ?
C10 C11 1.552(3) . ?
C11 O12 1.216(3) . ?
O13 H13 0.83(5) . ?
C14 C15 1.325(4) . ?
C14 H14A 0.9300 . ?
C14 H14B 0.9300 . ?
C15 C16 1.469(4) . ?
C16 N17 1.291(3) . ?
C16 O20 1.341(3) . ?
N17 C18 1.377(3) . ?
C18 N19 1.302(4) . ?
C18 C21 1.460(4) . ?
N19 O20 1.404(3) . ?
C21 C22 1.390(4) . ?
C21 C26 1.398(4) . ?
C22 C23 1.380(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.377(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.373(4) . ?
C24 N27 1.472(4) . ?
C25 C26 1.375(4) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
N27 O29 1.207(4) . ?
N27 O28 1.215(4) . ?
C30 C31 1.496(5) . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 N32 1.458(3) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
N32 C40 1.351(3) . ?
N32 C33 1.411(3) . ?
C33 C38 1.376(4) . ?
C33 C34 1.388(4) . ?
C34 C35 1.387(4) . ?
C34 H34 0.9300 . ?
C35 C36 1.366(5) . ?
C35 H35 0.9300 . ?
C36 C37 1.394(5) . ?
C36 H36 0.9300 . ?
C37 C38 1.379(4) . ?
C37 H37 0.9300 . ?
C38 C39 1.506(4) . ?
C39 O42 1.416(3) . ?
C39 C44 1.519(4) . ?
C39 C40 1.548(3) . ?
C40 O41 1.219(3) . ?
O42 H42 0.88(4) . ?
C43 C44 1.317(4) . ?
C43 H43A 0.9300 . ?
C43 H43B 0.9300 . ?
C44 C45 1.467(4) . ?
C45 N46 1.293(4) . ?
C45 O49 1.346(3) . ?
N46 C47 1.380(3) . ?
C47 N48 1.297(4) . ?
C47 C50 1.472(4) . ?
N48 O49 1.404(4) . ?
C50 C51 1.380(4) . ?
C50 C55 1.384(4) . ?
C51 C52 1.388(5) . ?
C51 H51 0.9300 . ?
C52 C53 1.366(5) . ?
C52 H52 0.9300 . ?
C53 C54 1.363(5) . ?
C53 N56 1.485(5) . ?
C54 C55 1.381(5) . ?
C54 H54 0.9300 . ?
C55 H55 0.9300 . ?
N56 O58 1.192(6) . ?
N56 O57 1.198(6) . ?
C59 C60 1.493(5) . ?
C59 H59A 0.9600 . ?
C59 H59B 0.9600 . ?
C59 H59C 0.9600 . ?
C60 N61 1.457(3) . ?
C60 H60A 0.9700 . ?
C60 H60B 0.9700 . ?
N61 C69 1.349(3) . ?
N61 C62 1.407(3) . ?
C62 C67 1.382(3) . ?
C62 C63 1.386(3) . ?
C63 C64 1.386(4) . ?
C63 H63 0.9300 . ?
C64 C65 1.375(5) . ?
C64 H64 0.9300 . ?
C65 C66 1.395(4) . ?
C65 H65 0.9300 . ?
C66 C67 1.375(4) . ?
C66 H66 0.9300 . ?
C67 C68 1.514(3) . ?
C68 O71 1.412(3) . ?
C68 C73 1.516(4) . ?
C68 C69 1.548(3) . ?
C69 O70 1.223(3) . ?
O71 H71 0.95(5) . ?
C72 C73 1.321(4) . ?
C72 H72A 0.9300 . ?
C72 H72B 0.9300 . ?
C73 C74 1.459(4) . ?
C74 N75 1.300(4) . ?
C74 O78 1.343(3) . ?
N75 C76 1.374(3) . ?
C76 N77 1.301(4) . ?
C76 C79 1.471(5) . ?
N77 O78 1.399(4) . ?
C79 C80 1.381(5) . ?
C79 C84 1.387(5) . ?
C80 C81 1.385(5) . ?
C80 H80 0.9300 . ?
C81 C82 1.362(7) . ?
C81 H81 0.9300 . ?
C82 C83 1.346(8) . ?
C82 N85A 1.439(9) . ?
C82 N85B 1.65(2) . ?
C83 C84 1.379(8) . ?
C83 H83 0.9300 . ?
C84 H84 0.9300 . ?
N85A O87A 1.225(16) . ?
N85A O86A 1.265(12) . ?
N85B O87B 1.11(2) . ?
N85B O86B 1.22(3) . ?
C88 C89 1.507(4) . ?
C88 H88A 0.9600 . ?
C88 H88B 0.9600 . ?
C88 H88C 0.9600 . ?
C89 N90 1.456(4) . ?
C89 H89A 0.9700 . ?
C89 H89B 0.9700 . ?
N90 C98 1.350(3) . ?
N90 C91 1.403(4) . ?
C91 C92 1.377(4) . ?
C91 C96 1.384(4) . ?
C92 C93 1.380(8) . ?
C92 H92 0.9300 . ?
C93 C94 1.365(9) . ?
C93 H93 0.9300 . ?
C94 C95 1.397(6) . ?
C94 H94 0.9300 . ?
C95 C96 1.360(5) . ?
C95 H95 0.9300 . ?
C96 C97 1.507(3) . ?
C97 O100 1.417(3) . ?
C97 C102 1.517(4) . ?
C97 C98 1.550(4) . ?
C98 O99 1.214(3) . ?
O100 H100 0.79(4) . ?
C101 C102 1.319(4) . ?
C101 H10A 0.9300 . ?
C101 H10B 0.9300 . ?
C102 C103 1.469(4) . ?
C103 N104 1.287(3) . ?
C103 O107 1.342(3) . ?
N104 C105 1.379(3) . ?
C105 N106 1.293(4) . ?
C105 C108 1.475(4) . ?
N106 O107 1.409(4) . ?
C108 C109 1.386(4) . ?
C108 C113 1.393(4) . ?
C109 C110 1.379(4) . ?
C109 H109 0.9300 . ?
C110 C111 1.378(4) . ?
C110 H110 0.9300 . ?
C111 C112 1.373(4) . ?
C111 N114 1.474(3) . ?
C112 C113 1.377(4) . ?
C112 H112 0.9300 . ?
C113 H113 0.9300 . ?
N114 O116 1.217(4) . ?
N114 O115 1.218(3) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C2 H2A O28 0.97 2.43 3.379(4) 167.4 2_546 yes
C89 H89A O86A^a 0.97 2.41 3.300(9) 152.3 2_757 yes
O13 H13 O41 0.83(5) 2.05(5) 2.836(3) 158(4) . yes
O42 H42 O12 0.88(4) 2.08(4) 2.841(3) 144(3) . yes
O71 H71 O99 0.95(5) 1.90(5) 2.777(3) 152(4) . yes
O100 H100 O70 0.79(4) 2.01(4) 2.756(3) 156(4) . yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 N3 C11 96.2(3) . . . . ?
C1 C2 N3 C4 -80.1(3) . . . . ?
C11 N3 C4 C5 180.0(2) . . . . ?
C2 N3 C4 C5 -3.4(4) . . . . ?
C11 N3 C4 C9 1.9(3) . . . . ?
C2 N3 C4 C9 178.5(2) . . . . ?
C9 C4 C5 C6 0.1(4) . . . . ?
N3 C4 C5 C6 -177.8(2) . . . . ?
C4 C5 C6 C7 -0.2(4) . . . . ?
C5 C6 C7 C8 -0.1(5) . . . . ?
C6 C7 C8 C9 0.6(4) . . . . ?
C7 C8 C9 C4 -0.7(4) . . . . ?
C7 C8 C9 C10 175.9(2) . . . . ?
C5 C4 C9 C8 0.4(4) . . . . ?
N3 C4 C9 C8 178.6(2) . . . . ?
C5 C4 C9 C10 -176.9(2) . . . . ?
N3 C4 C9 C10 1.3(3) . . . . ?
C8 C9 C10 O13 -67.4(3) . . . . ?
C4 C9 C10 O13 109.6(2) . . . . ?
C8 C9 C10 C15 58.9(3) . . . . ?
C4 C9 C10 C15 -124.2(2) . . . . ?
C8 C9 C10 C11 179.6(2) . . . . ?
C4 C9 C10 C11 -3.5(2) . . . . ?
C4 N3 C11 O12 179.2(2) . . . . ?
C2 N3 C11 O12 2.5(4) . . . . ?
C4 N3 C11 C10 -4.2(2) . . . . ?
C2 N3 C11 C10 179.1(2) . . . . ?
O13 C10 C11 O12 68.0(3) . . . . ?
C9 C10 C11 O12 -178.7(2) . . . . ?
C15 C10 C11 O12 -54.8(3) . . . . ?
O13 C10 C11 N3 -108.7(2) . . . . ?
C9 C10 C11 N3 4.6(2) . . . . ?
C15 C10 C11 N3 128.5(2) . . . . ?
O13 C10 C15 C14 3.9(4) . . . . ?
C9 C10 C15 C14 -120.4(3) . . . . ?
C11 C10 C15 C14 124.3(3) . . . . ?
O13 C10 C15 C16 -173.9(2) . . . . ?
C9 C10 C15 C16 61.9(3) . . . . ?
C11 C10 C15 C16 -53.5(3) . . . . ?
C14 C15 C16 N17 178.6(3) . . . . ?
C10 C15 C16 N17 -3.5(4) . . . . ?
C14 C15 C16 O20 -2.6(4) . . . . ?
C10 C15 C16 O20 175.2(2) . . . . ?
O20 C16 N17 C18 0.3(3) . . . . ?
C15 C16 N17 C18 179.1(3) . . . . ?
C16 N17 C18 N19 -0.2(3) . . . . ?
C16 N17 C18 C21 179.6(2) . . . . ?
N17 C18 N19 O20 0.0(4) . . . . ?
C21 C18 N19 O20 -179.8(2) . . . . ?
N17 C16 O20 N19 -0.4(3) . . . . ?
C15 C16 O20 N19 -179.3(2) . . . . ?
C18 N19 O20 C16 0.2(4) . . . . ?
N19 C18 C21 C22 179.6(3) . . . . ?
N17 C18 C21 C22 -0.2(4) . . . . ?
N19 C18 C21 C26 1.3(4) . . . . ?
N17 C18 C21 C26 -178.5(3) . . . . ?
C26 C21 C22 C23 0.2(4) . . . . ?
C18 C21 C22 C23 -178.1(2) . . . . ?
C21 C22 C23 C24 -0.5(4) . . . . ?
C22 C23 C24 C25 -0.4(4) . . . . ?
C22 C23 C24 N27 177.3(3) . . . . ?
C23 C24 C25 C26 1.8(5) . . . . ?
N27 C24 C25 C26 -176.0(3) . . . . ?
C24 C25 C26 C21 -2.1(5) . . . . ?
C22 C21 C26 C25 1.2(5) . . . . ?
C18 C21 C26 C25 179.5(3) . . . . ?
C25 C24 N27 O29 169.1(3) . . . . ?
C23 C24 N27 O29 -8.7(4) . . . . ?
C25 C24 N27 O28 -10.9(4) . . . . ?
C23 C24 N27 O28 171.2(3) . . . . ?
C30 C31 N32 C40 97.7(3) . . . . ?
C30 C31 N32 C33 -84.4(4) . . . . ?
C40 N32 C33 C38 1.1(3) . . . . ?
C31 N32 C33 C38 -177.0(2) . . . . ?
C40 N32 C33 C34 179.1(3) . . . . ?
C31 N32 C33 C34 0.9(4) . . . . ?
C38 C33 C34 C35 0.3(4) . . . . ?
N32 C33 C34 C35 -177.4(3) . . . . ?
C33 C34 C35 C36 0.2(5) . . . . ?
C34 C35 C36 C37 -0.3(5) . . . . ?
C35 C36 C37 C38 -0.1(5) . . . . ?
C34 C33 C38 C37 -0.8(4) . . . . ?
N32 C33 C38 C37 177.3(2) . . . . ?
C34 C33 C38 C39 -178.1(2) . . . . ?
N32 C33 C38 C39 0.0(3) . . . . ?
C36 C37 C38 C33 0.7(4) . . . . ?
C36 C37 C38 C39 177.4(3) . . . . ?
C33 C38 C39 O42 113.4(2) . . . . ?
C37 C38 C39 O42 -63.6(3) . . . . ?
C33 C38 C39 C44 -121.7(2) . . . . ?
C37 C38 C39 C44 61.3(4) . . . . ?
C33 C38 C39 C40 -0.9(3) . . . . ?
C37 C38 C39 C40 -177.9(3) . . . . ?
C33 N32 C40 O41 -176.8(3) . . . . ?
C31 N32 C40 O41 1.3(4) . . . . ?
C33 N32 C40 C39 -1.7(3) . . . . ?
C31 N32 C40 C39 176.5(2) . . . . ?
O42 C39 C40 O41 62.6(3) . . . . ?
C38 C39 C40 O41 176.7(3) . . . . ?
C44 C39 C40 O41 -62.0(3) . . . . ?
O42 C39 C40 N32 -112.6(2) . . . . ?
C38 C39 C40 N32 1.6(3) . . . . ?
C44 C39 C40 N32 122.8(2) . . . . ?
O42 C39 C44 C43 1.7(4) . . . . ?
C38 C39 C44 C43 -121.3(3) . . . . ?
C40 C39 C44 C43 124.6(3) . . . . ?
O42 C39 C44 C45 -179.5(2) . . . . ?
C38 C39 C44 C45 57.5(3) . . . . ?
C40 C39 C44 C45 -56.7(3) . . . . ?
C43 C44 C45 N46 -176.9(3) . . . . ?
C39 C44 C45 N46 4.4(4) . . . . ?
C43 C44 C45 O49 5.0(4) . . . . ?
C39 C44 C45 O49 -173.7(2) . . . . ?
O49 C45 N46 C47 0.8(3) . . . . ?
C44 C45 N46 C47 -177.4(3) . . . . ?
C45 N46 C47 N48 -0.4(3) . . . . ?
C45 N46 C47 C50 178.5(3) . . . . ?
N46 C47 N48 O49 -0.1(4) . . . . ?
C50 C47 N48 O49 -179.0(2) . . . . ?
N46 C45 O49 N48 -0.8(3) . . . . ?
C44 C45 O49 N48 177.6(3) . . . . ?
C47 N48 O49 C45 0.5(3) . . . . ?
N48 C47 C50 C51 -163.3(3) . . . . ?
N46 C47 C50 C51 18.0(4) . . . . ?
N48 C47 C50 C55 18.5(4) . . . . ?
N46 C47 C50 C55 -160.3(3) . . . . ?
C55 C50 C51 C52 -1.7(5) . . . . ?
C47 C50 C51 C52 -180.0(3) . . . . ?
C50 C51 C52 C53 0.2(6) . . . . ?
C51 C52 C53 C54 1.5(6) . . . . ?
C51 C52 C53 N56 -178.5(3) . . . . ?
C52 C53 C54 C55 -1.7(5) . . . . ?
N56 C53 C54 C55 178.3(3) . . . . ?
C53 C54 C55 C50 0.2(5) . . . . ?
C51 C50 C55 C54 1.5(4) . . . . ?
C47 C50 C55 C54 179.8(3) . . . . ?
C54 C53 N56 O58 -164.1(4) . . . . ?
C52 C53 N56 O58 16.0(6) . . . . ?
C54 C53 N56 O57 12.7(6) . . . . ?
C52 C53 N56 O57 -167.3(5) . . . . ?
C59 C60 N61 C69 98.9(3) . . . . ?
C59 C60 N61 C62 -78.8(3) . . . . ?
C69 N61 C62 C67 2.9(3) . . . . ?
C60 N61 C62 C67 -179.2(2) . . . . ?
C69 N61 C62 C63 -176.5(2) . . . . ?
C60 N61 C62 C63 1.4(4) . . . . ?
C67 C62 C63 C64 0.4(3) . . . . ?
N61 C62 C63 C64 179.8(2) . . . . ?
C62 C63 C64 C65 -0.3(4) . . . . ?
C63 C64 C65 C66 -0.4(4) . . . . ?
C64 C65 C66 C67 1.0(4) . . . . ?
C65 C66 C67 C62 -0.8(4) . . . . ?
C65 C66 C67 C68 179.1(3) . . . . ?
C63 C62 C67 C66 0.1(3) . . . . ?
N61 C62 C67 C66 -179.3(2) . . . . ?
C63 C62 C67 C68 -179.8(2) . . . . ?
N61 C62 C67 C68 0.7(3) . . . . ?
C66 C67 C68 O71 -69.4(3) . . . . ?
C62 C67 C68 O71 110.5(2) . . . . ?
C66 C67 C68 C73 55.8(3) . . . . ?
C62 C67 C68 C73 -124.3(2) . . . . ?
C66 C67 C68 C69 176.6(2) . . . . ?
C62 C67 C68 C69 -3.4(2) . . . . ?
C62 N61 C69 O70 177.5(2) . . . . ?
C60 N61 C69 O70 -0.5(4) . . . . ?
C62 N61 C69 C68 -5.1(2) . . . . ?
C60 N61 C69 C68 176.9(2) . . . . ?
O71 C68 C69 O70 68.7(3) . . . . ?
C67 C68 C69 O70 -177.5(2) . . . . ?
C73 C68 C69 O70 -55.2(3) . . . . ?
O71 C68 C69 N61 -108.6(2) . . . . ?
C67 C68 C69 N61 5.2(2) . . . . ?
C73 C68 C69 N61 127.5(2) . . . . ?
O71 C68 C73 C72 -0.8(4) . . . . ?
C67 C68 C73 C72 -124.2(3) . . . . ?
C69 C68 C73 C72 121.3(3) . . . . ?
O71 C68 C73 C74 177.7(2) . . . . ?
C67 C68 C73 C74 54.3(3) . . . . ?
C69 C68 C73 C74 -60.2(3) . . . . ?
C72 C73 C74 N75 -179.0(3) . . . . ?
C68 C73 C74 N75 2.5(4) . . . . ?
C72 C73 C74 O78 2.2(4) . . . . ?
C68 C73 C74 O78 -176.4(2) . . . . ?
O78 C74 N75 C76 2.0(3) . . . . ?
C73 C74 N75 C76 -176.9(3) . . . . ?
C74 N75 C76 N77 -1.7(3) . . . . ?
C74 N75 C76 C79 177.1(3) . . . . ?
N75 C76 N77 O78 0.7(3) . . . . ?
C79 C76 N77 O78 -178.1(3) . . . . ?
N75 C74 O78 N77 -1.6(3) . . . . ?
C73 C74 O78 N77 177.4(2) . . . . ?
C76 N77 O78 C74 0.5(3) . . . . ?
N77 C76 C79 C80 -171.8(3) . . . . ?
N75 C76 C79 C80 9.4(4) . . . . ?
N77 C76 C79 C84 9.3(5) . . . . ?
N75 C76 C79 C84 -169.4(3) . . . . ?
C84 C79 C80 C81 0.8(5) . . . . ?
C76 C79 C80 C81 -178.1(3) . . . . ?
C79 C80 C81 C82 0.8(5) . . . . ?
C80 C81 C82 C83 -2.4(6) . . . . ?
C80 C81 C82 N85A 174.6(5) . . . . ?
C80 C81 C82 N85B -176.8(8) . . . . ?
C81 C82 C83 C84 2.5(8) . . . . ?
N85A C82 C83 C84 -174.8(5) . . . . ?
N85B C82 C83 C84 174.5(11) . . . . ?
C82 C83 C84 C79 -0.8(7) . . . . ?
C80 C79 C84 C83 -0.8(6) . . . . ?
C76 C79 C84 C83 178.1(4) . . . . ?
C83 C82 N85A O87A -169.4(8) . . . . ?
C81 C82 N85A O87A 13.4(10) . . . . ?
C83 C82 N85A O86A 9.6(9) . . . . ?
C81 C82 N85A O86A -167.7(6) . . . . ?
C83 C82 N85B O87B -142(2) . . . . ?
C81 C82 N85B O87B 31(3) . . . . ?
C83 C82 N85B O86B 31(2) . . . . ?
C81 C82 N85B O86B -155.6(14) . . . . ?
C88 C89 N90 C98 100.8(3) . . . . ?
C88 C89 N90 C91 -77.5(4) . . . . ?
C98 N90 C91 C92 177.7(3) . . . . ?
C89 N90 C91 C92 -3.8(5) . . . . ?
C98 N90 C91 C96 0.6(3) . . . . ?
C89 N90 C91 C96 179.1(2) . . . . ?
C96 C91 C92 C93 0.7(6) . . . . ?
N90 C91 C92 C93 -176.0(4) . . . . ?
C91 C92 C93 C94 0.3(9) . . . . ?
C92 C93 C94 C95 -1.1(10) . . . . ?
C93 C94 C95 C96 0.9(9) . . . . ?
C94 C95 C96 C91 0.1(6) . . . . ?
C94 C95 C96 C97 174.6(4) . . . . ?
C92 C91 C96 C95 -0.9(5) . . . . ?
N90 C91 C96 C95 176.3(3) . . . . ?
C92 C91 C96 C97 -176.6(3) . . . . ?
N90 C91 C96 C97 0.6(3) . . . . ?
C95 C96 C97 O100 -61.9(4) . . . . ?
C91 C96 C97 O100 113.1(2) . . . . ?
C95 C96 C97 C102 62.6(4) . . . . ?
C91 C96 C97 C102 -122.4(3) . . . . ?
C95 C96 C97 C98 -176.5(4) . . . . ?
C91 C96 C97 C98 -1.4(3) . . . . ?
C91 N90 C98 O99 -178.3(3) . . . . ?
C89 N90 C98 O99 3.2(4) . . . . ?
C91 N90 C98 C97 -1.6(3) . . . . ?
C89 N90 C98 C97 180.0(2) . . . . ?
O100 C97 C98 O99 64.6(3) . . . . ?
C96 C97 C98 O99 178.6(3) . . . . ?
C102 C97 C98 O99 -58.7(3) . . . . ?
O100 C97 C98 N90 -112.2(2) . . . . ?
C96 C97 C98 N90 1.8(2) . . . . ?
C102 C97 C98 N90 124.5(2) . . . . ?
O100 C97 C102 C101 11.7(4) . . . . ?
C96 C97 C102 C101 -111.3(3) . . . . ?
C98 C97 C102 C101 133.8(3) . . . . ?
O100 C97 C102 C103 -169.3(2) . . . . ?
C96 C97 C102 C103 67.7(3) . . . . ?
C98 C97 C102 C103 -47.2(3) . . . . ?
C101 C102 C103 N104 163.2(3) . . . . ?
C97 C102 C103 N104 -15.8(4) . . . . ?
C101 C102 C103 O107 -15.7(4) . . . . ?
C97 C102 C103 O107 165.3(2) . . . . ?
O107 C103 N104 C105 1.3(3) . . . . ?
C102 C103 N104 C105 -177.6(3) . . . . ?
C103 N104 C105 N106 -1.1(3) . . . . ?
C103 N104 C105 C108 177.2(3) . . . . ?
N104 C105 N106 O107 0.4(4) . . . . ?
C108 C105 N106 O107 -177.9(3) . . . . ?
N104 C103 O107 N106 -1.1(4) . . . . ?
C102 C103 O107 N106 177.9(3) . . . . ?
C105 N106 O107 C103 0.4(4) . . . . ?
N106 C105 C108 C109 179.0(3) . . . . ?
N104 C105 C108 C109 0.9(4) . . . . ?
N106 C105 C108 C113 1.5(5) . . . . ?
N104 C105 C108 C113 -176.6(3) . . . . ?
C113 C108 C109 C110 0.2(4) . . . . ?
C105 C108 C109 C110 -177.4(3) . . . . ?
C108 C109 C110 C111 -1.0(4) . . . . ?
C109 C110 C111 C112 0.6(4) . . . . ?
C109 C110 C111 N114 -179.8(3) . . . . ?
C110 C111 C112 C113 0.6(5) . . . . ?
N114 C111 C112 C113 -178.9(3) . . . . ?
C111 C112 C113 C108 -1.5(5) . . . . ?
C109 C108 C113 C112 1.1(5) . . . . ?
C105 C108 C113 C112 178.6(3) . . . . ?
C112 C111 N114 O116 155.2(3) . . . . ?
C110 C111 N114 O116 -24.3(4) . . . . ?
C112 C111 N114 O115 -23.4(4) . . . . ?
C110 C111 N114 O115 157.1(3) . . . . ?
