#------------------------------------------------------------------------------
#$Date: 2021-03-05 19:43:22 +0100 (vie 05 de mar de 2021) $
#$Revision: 262771 $
#$URL: svn://www.crystallography.net/cod/cif/1/56/00/1560043.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_1560043
loop_
_publ_author_name
'Rajkumar, Madhu'
'Desiraju, Gautam R.'
_publ_section_title
;
 Quaternary and quinary molecular solids based on structural inequivalence
 and combinatorial approaches: 2-nitroresorcinol and
 4,6-dichlororesorcinol
;
_journal_issue                   2
_journal_name_full               IUCrJ
_journal_page_first              178
_journal_page_last               185
_journal_paper_doi               10.1107/S2052252520016589
_journal_volume                  8
_journal_year                    2021
_chemical_formula_sum            'C32 H23 N3 O3.99'
_chemical_formula_weight         513.33
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                93.232(7)
_cell_angle_beta                 102.634(7)
_cell_angle_gamma                97.795(7)
_cell_formula_units_Z            4
_cell_length_a                   9.2447(9)
_cell_length_b                   14.4694(13)
_cell_length_c                   19.3202(18)
_cell_measurement_reflns_used    20527
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.6
_cell_measurement_theta_min      3.0
_cell_volume                     2488.6(4)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0450
_diffrn_reflns_av_unetI/netI     0.0601
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            25721
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         3.042
_diffrn_source                   'Sealed Tube'
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.762
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_description       Block
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.170
_refine_diff_density_max         0.576
_refine_diff_density_min         -0.400
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     729
_refine_ls_number_reflns         11355
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0890
_refine_ls_R_factor_gt           0.0567
_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)+(0.0665P)²+0.7465P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1419
_refine_ls_wR_factor_ref         0.1588
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7523
_reflns_number_total             11355
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            yc5029.cif
_cod_data_source_block           3NRES-ACR
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/IUCr/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 1560041--1560072.cif.
;
_cod_database_code               1560043
_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   0.974
_shelx_estimated_absorpt_t_max   0.985
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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
N1 N 1.02767(19) 0.09475(10) 0.43919(8) 0.0241(4) Uani 1 1 d . . . . .
C40 C 0.8842(2) 0.11091(13) 0.42520(10) 0.0249(4) Uani 1 1 d . . . . .
C41 C 0.7959(3) 0.09336(15) 0.35405(11) 0.0346(5) Uani 1 1 d . . . . .
H41 H 0.838130 0.071641 0.317946 0.041 Uiso 1 1 calc R U . . .
C42 C 0.6510(3) 0.10808(16) 0.33857(13) 0.0426(6) Uani 1 1 d . . . . .
H42 H 0.594862 0.096223 0.291924 0.051 Uiso 1 1 calc R U . . .
C43 C 0.5838(3) 0.14139(16) 0.39269(14) 0.0428(6) Uani 1 1 d . . . . .
H43 H 0.484524 0.151522 0.381117 0.051 Uiso 1 1 calc R U . . .
C44 C 0.6635(2) 0.15847(14) 0.46098(12) 0.0346(5) Uani 1 1 d . . . . .
H44 H 0.617995 0.179719 0.495980 0.042 Uiso 1 1 calc R U . . .
C45 C 0.8163(2) 0.14427(13) 0.47990(11) 0.0260(4) Uani 1 1 d . . . . .
C46 C 0.9031(2) 0.16090(13) 0.54892(10) 0.0254(4) Uani 1 1 d . . . . .
H46 H 0.861547 0.181898 0.585491 0.031 Uiso 1 1 calc R U . . .
C47 C 1.0527(2) 0.14621(12) 0.56374(10) 0.0232(4) Uani 1 1 d . . . . .
C48 C 1.1477(2) 0.16304(14) 0.63360(10) 0.0297(5) Uani 1 1 d . . . . .
H48 H 1.110734 0.185029 0.671451 0.036 Uiso 1 1 calc R U . . .
C49 C 1.2923(3) 0.14686(15) 0.64478(11) 0.0336(5) Uani 1 1 d . . . . .
H49 H 1.353879 0.158372 0.690342 0.040 Uiso 1 1 calc R U . . .
C50 C 1.3504(2) 0.11272(14) 0.58791(11) 0.0322(5) Uani 1 1 d . . . . .
H50 H 1.449253 0.101702 0.596708 0.039 Uiso 1 1 calc R U . . .
C51 C 1.2635(2) 0.09588(13) 0.52075(11) 0.0275(4) Uani 1 1 d . . . . .
H51 H 1.303298 0.073511 0.483994 0.033 Uiso 1 1 calc R U . . .
C52 C 1.1117(2) 0.11231(12) 0.50630(10) 0.0227(4) Uani 1 1 d . . . . .
N2 N 0.48018(18) 0.41106(10) 0.42076(8) 0.0223(3) Uani 1 1 d . . . . .
C27 C 0.2460(2) 0.41349(14) 0.33878(11) 0.0304(5) Uani 1 1 d . . . . .
H27 H 0.296503 0.437734 0.305578 0.037 Uiso 1 1 calc R U . . .
C28 C 0.0938(3) 0.39716(16) 0.32272(12) 0.0389(5) Uani 1 1 d . . . . .
H28 H 0.041158 0.410527 0.278555 0.047 Uiso 1 1 calc R U . . .
C29 C 0.0137(3) 0.35985(15) 0.37253(13) 0.0382(5) Uani 1 1 d . . . . .
H29 H -0.090588 0.348414 0.360555 0.046 Uiso 1 1 calc R U . . .
C30 C 0.0887(2) 0.34108(14) 0.43700(12) 0.0316(5) Uani 1 1 d . . . . .
H30 H 0.035230 0.317468 0.469341 0.038 Uiso 1 1 calc R U . . .
C31 C 0.2486(2) 0.35680(13) 0.45651(10) 0.0244(4) Uani 1 1 d . . . . .
C32 C 0.3311(2) 0.33894(13) 0.52234(10) 0.0253(4) Uani 1 1 d . . . . .
H32 H 0.281716 0.316303 0.556418 0.030 Uiso 1 1 calc R U . . .
C33 C 0.4875(2) 0.35472(12) 0.53763(10) 0.0223(4) Uani 1 1 d . . . . .
C34 C 0.5787(2) 0.33647(14) 0.60361(10) 0.0293(5) Uani 1 1 d . . . . .
H34 H 0.533717 0.313136 0.638937 0.035 Uiso 1 1 calc R U . . .
C35 C 0.7306(2) 0.35284(14) 0.61534(11) 0.0315(5) Uani 1 1 d . . . . .
H35 H 0.788768 0.340183 0.658457 0.038 Uiso 1 1 calc R U . . .
C36 C 0.8013(2) 0.38928(13) 0.56201(11) 0.0293(5) Uani 1 1 d . . . . .
H36 H 0.905446 0.400151 0.570719 0.035 Uiso 1 1 calc R U . . .
C37 C 0.7189(2) 0.40834(13) 0.49872(10) 0.0257(4) Uani 1 1 d . . . . .
H37 H 0.766997 0.432658 0.464696 0.031 Uiso 1 1 calc R U . . .
C38 C 0.5595(2) 0.39142(12) 0.48398(10) 0.0210(4) Uani 1 1 d . . . . .
C39 C 0.3287(2) 0.39374(13) 0.40614(10) 0.0234(4) Uani 1 1 d . . . . .
C20 C 0.4392(2) 0.83894(13) 0.06174(10) 0.0263(4) Uani 1 1 d . . . . .
H20 H 0.395732 0.815663 0.097540 0.032 Uiso 1 1 calc R U . . .
C14 C 0.5947(2) 0.86094(13) 0.07412(10) 0.0251(4) Uani 1 1 d . . . . .
C15 C 0.6928(3) 0.85036(14) 0.13999(11) 0.0329(5) Uani 1 1 d . . . . .
H15 H 0.653314 0.828299 0.177326 0.040 Uiso 1 1 calc R U . . .
C16 C 0.8440(3) 0.87223(15) 0.14890(12) 0.0372(5) Uani 1 1 d . . . . .
H16 H 0.907172 0.865628 0.192372 0.045 Uiso 1 1 calc R U . . .
C17 C 0.9055(3) 0.90497(14) 0.09224(12) 0.0352(5) Uani 1 1 d . . . . .
H17 H 1.009106 0.918499 0.098739 0.042 Uiso 1 1 calc R U . . .
C18 C 0.8162(2) 0.91702(13) 0.02857(11) 0.0300(5) Uani 1 1 d . . . . .
H18 H 0.858966 0.939215 -0.007771 0.036 Uiso 1 1 calc R U . . .
C19 C 0.6569(2) 0.89577(12) 0.01715(10) 0.0233(4) Uani 1 1 d . . . . .
N3 N 0.57066(19) 0.90952(10) -0.04613(8) 0.0238(4) Uani 1 1 d . . . . .
C21 C 0.4200(2) 0.88807(12) -0.05718(10) 0.0233(4) Uani 1 1 d . . . . .
C22 C 0.3286(2) 0.90207(13) -0.12401(10) 0.0290(5) Uani 1 1 d . . . . .
H22 H 0.372767 0.926544 -0.159229 0.035 Uiso 1 1 calc R U . . .
C23 C 0.1772(3) 0.87994(14) -0.13671(12) 0.0355(5) Uani 1 1 d . . . . .
H23 H 0.118821 0.888921 -0.180837 0.043 Uiso 1 1 calc R U . . .
C24 C 0.1063(3) 0.84330(15) -0.08377(13) 0.0377(5) Uani 1 1 d . . . . .
H24 H 0.002423 0.827899 -0.093720 0.045 Uiso 1 1 calc R U . . .
C25 C 0.1887(2) 0.83067(13) -0.01910(12) 0.0316(5) Uani 1 1 d . . . . .
H25 H 0.140946 0.808273 0.015597 0.038 Uiso 1 1 calc R U . . .
C26 C 0.3487(2) 0.85138(12) -0.00342(10) 0.0239(4) Uani 1 1 d . . . . .
C7 C 0.0092(2) 0.66044(13) 0.08920(10) 0.0264(4) Uani 1 1 d . . . . .
H7 H -0.021595 0.681285 0.129285 0.032 Uiso 1 1 calc R U . . .
C1 C 0.1535(2) 0.63897(13) 0.09619(10) 0.0255(4) Uani 1 1 d . . . . .
C2 C 0.2603(3) 0.64742(14) 0.16295(11) 0.0318(5) Uani 1 1 d . . . . .
H2 H 0.234109 0.668352 0.204270 0.038 Uiso 1 1 calc R U . . .
C3 C 0.4002(3) 0.62507(15) 0.16655(12) 0.0349(5) Uani 1 1 d . . . . .
H3 H 0.468324 0.630023 0.210332 0.042 Uiso 1 1 calc R U . . .
C4 C 0.4423(3) 0.59434(15) 0.10392(12) 0.0347(5) Uani 1 1 d . . . . .
H4 H 0.538578 0.580251 0.106995 0.042 Uiso 1 1 calc R U . . .
C5 C 0.3440(2) 0.58507(13) 0.03918(11) 0.0294(5) Uani 1 1 d . . . . .
H5 H 0.373774 0.564671 -0.001303 0.035 Uiso 1 1 calc R U . . .
C6 C 0.1963(2) 0.60636(12) 0.03313(10) 0.0236(4) Uani 1 1 d . . . . .
N4 N 0.10118(19) 0.59591(10) -0.03158(8) 0.0245(4) Uani 1 1 d . . . . .
C8 C -0.0382(2) 0.61774(13) -0.03747(10) 0.0251(4) Uani 1 1 d . . . . .
C9 C -0.1382(2) 0.60792(14) -0.10569(11) 0.0305(5) Uani 1 1 d . . . . .
H9 H -0.106934 0.586500 -0.145464 0.037 Uiso 1 1 calc R U . . .
C10 C -0.2794(3) 0.62957(14) -0.11335(12) 0.0343(5) Uani 1 1 d . . . . .
H10 H -0.343385 0.622831 -0.158347 0.041 Uiso 1 1 calc R U . . .
C11 C -0.3302(3) 0.66231(14) -0.05352(13) 0.0360(5) Uani 1 1 d . . . . .
H11 H -0.426623 0.677262 -0.059638 0.043 Uiso 1 1 calc R U . . .
C12 C -0.2386(2) 0.67184(14) 0.01249(12) 0.0312(5) Uani 1 1 d . . . . .
H12 H -0.273606 0.692196 0.051433 0.037 Uiso 1 1 calc R U . . .
C13 C -0.0892(2) 0.65104(13) 0.02297(10) 0.0250(4) Uani 1 1 d . . . . .
O1 O 0.85130(18) 0.49834(9) 0.14411(8) 0.0352(4) Uani 1 1 d . . . . .
H1 H 0.857900 0.463880 0.110121 0.053 Uiso 1 1 calc R U . . .
O2 O 0.63299(17) 0.51091(9) 0.34051(7) 0.0309(3) Uani 1 1 d . . . . .
H2A H 0.582844 0.479150 0.363210 0.046 Uiso 1 1 calc R U . . .
O5 O 0.9096(2) 0.61645(12) 0.31244(10) 0.0618(6) Uani 1 1 d . . . . .
O6 O 0.7650(2) 0.65495(10) 0.22096(9) 0.0475(4) Uani 1 1 d . . . . .
N6 N 0.80915(18) 0.59709(11) 0.25947(8) 0.0232(4) Uani 1 1 d . . . . .
C53 C 0.7414(2) 0.49862(12) 0.24225(9) 0.0194(4) Uani 1 1 d . . . . .
C54 C 0.7690(2) 0.44999(13) 0.18366(9) 0.0221(4) Uani 1 1 d . . . . .
C55 C 0.7147(2) 0.35471(13) 0.17041(10) 0.0262(4) Uani 1 1 d . . . . .
H55 H 0.732634 0.320126 0.131934 0.031 Uiso 1 1 calc R U . . .
C56 C 0.6337(2) 0.31216(13) 0.21537(10) 0.0270(4) Uani 1 1 d . . . . .
H56 H 0.598597 0.248269 0.206826 0.032 Uiso 1 1 calc R U . . .
C57 C 0.6031(2) 0.36130(13) 0.27243(10) 0.0258(4) Uani 1 1 d . . . . .
H57 H 0.546180 0.330955 0.300969 0.031 Uiso 1 1 calc R U . . .
C58 C 0.6578(2) 0.45657(13) 0.28712(9) 0.0215(4) Uani 1 1 d . . . . .
O3 O 0.14648(19) -0.00245(10) 0.35063(7) 0.0354(4) Uani 1 1 d . . . . .
H3A H 0.106887 0.030186 0.374830 0.053 Uiso 1 1 calc R U . . .
O4 O 0.32772(18) -0.00928(9) 0.14213(7) 0.0328(4) Uani 1 1 d . . . . .
H4A H 0.355296 0.024294 0.113214 0.049 Uiso 1 1 calc R U . . .
N5 N 0.26203(19) -0.09878(11) 0.25486(9) 0.0246(4) Uani 1 1 d . . . . .
C59 C 0.2409(2) -0.00080(12) 0.24754(9) 0.0200(4) Uani 1 1 d . . . . .
C60 C 0.1845(2) 0.04575(13) 0.29861(9) 0.0221(4) Uani 1 1 d . . . . .
C61 C 0.1745(2) 0.14063(13) 0.29335(10) 0.0256(4) Uani 1 1 d . . . . .
H61 H 0.138329 0.173902 0.326814 0.031 Uiso 1 1 calc R U . . .
C62 C 0.2188(2) 0.18499(13) 0.23793(10) 0.0273(4) Uani 1 1 d . . . . .
H62 H 0.213193 0.248406 0.235151 0.033 Uiso 1 1 calc R U . . .
C63 C 0.2712(2) 0.13734(13) 0.18670(10) 0.0253(4) Uani 1 1 d . . . . .
H63 H 0.298389 0.168404 0.149563 0.030 Uiso 1 1 calc R U . . .
C64 C 0.2831(2) 0.04297(13) 0.19076(9) 0.0216(4) Uani 1 1 d . . . . .
O8 O 0.1573(2) -0.15747(13) 0.25752(16) 0.0356(9) Uani 0.770(7) 1 d . . . . .
O7 O 0.3913(2) -0.11700(14) 0.26010(18) 0.0427(10) Uani 0.800(8) 1 d . . . . .
O12 O 0.1801(11) -0.1557(5) 0.2054(6) 0.047(4) Uani 0.203(8) 1 d . . . . .
O11 O 0.3353(15) -0.1184(6) 0.3042(7) 0.058(5) Uani 0.202(9) 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 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
C52 N1 C40 119.35(16) . . ?
N1 C40 C41 119.31(18) . . ?
N1 C40 C45 122.12(18) . . ?
C41 C40 C45 118.57(19) . . ?
C42 C41 C40 120.6(2) . . ?
C42 C41 H41 119.7 . . ?
C40 C41 H41 119.7 . . ?
C41 C42 C43 120.9(2) . . ?
C41 C42 H42 119.6 . . ?
C43 C42 H42 119.6 . . ?
C44 C43 C42 120.4(2) . . ?
C44 C43 H43 119.8 . . ?
C42 C43 H43 119.8 . . ?
C43 C44 C45 120.8(2) . . ?
C43 C44 H44 119.6 . . ?
C45 C44 H44 119.6 . . ?
C46 C45 C44 123.18(19) . . ?
C46 C45 C40 118.07(18) . . ?
C44 C45 C40 118.75(19) . . ?
C45 C46 C47 120.26(18) . . ?
C45 C46 H46 119.9 . . ?
C47 C46 H46 119.9 . . ?
C46 C47 C48 122.68(18) . . ?
C46 C47 C52 118.21(18) . . ?
C48 C47 C52 119.10(18) . . ?
C49 C48 C47 119.96(19) . . ?
C49 C48 H48 120.0 . . ?
C47 C48 H48 120.0 . . ?
C48 C49 C50 120.9(2) . . ?
C48 C49 H49 119.6 . . ?
C50 C49 H49 119.6 . . ?
C51 C50 C49 120.9(2) . . ?
C51 C50 H50 119.6 . . ?
C49 C50 H50 119.6 . . ?
C50 C51 C52 120.32(19) . . ?
C50 C51 H51 119.8 . . ?
C52 C51 H51 119.8 . . ?
N1 C52 C51 119.18(17) . . ?
N1 C52 C47 121.96(18) . . ?
C51 C52 C47 118.86(18) . . ?
C38 N2 C39 119.52(16) . . ?
C28 C27 C39 120.4(2) . . ?
C28 C27 H27 119.8 . . ?
C39 C27 H27 119.8 . . ?
C27 C28 C29 120.9(2) . . ?
C27 C28 H28 119.5 . . ?
C29 C28 H28 119.5 . . ?
C30 C29 C28 120.1(2) . . ?
C30 C29 H29 119.9 . . ?
C28 C29 H29 119.9 . . ?
C29 C30 C31 121.2(2) . . ?
C29 C30 H30 119.4 . . ?
C31 C30 H30 119.4 . . ?
C32 C31 C30 123.40(18) . . ?
C32 C31 C39 118.10(18) . . ?
C30 C31 C39 118.50(18) . . ?
C31 C32 C33 120.47(17) . . ?
C31 C32 H32 119.8 . . ?
C33 C32 H32 119.8 . . ?
C32 C33 C34 123.30(17) . . ?
C32 C33 C38 118.00(17) . . ?
C34 C33 C38 118.70(18) . . ?
C35 C34 C33 120.65(18) . . ?
C35 C34 H34 119.7 . . ?
C33 C34 H34 119.7 . . ?
C34 C35 C36 120.41(19) . . ?
C34 C35 H35 119.8 . . ?
C36 C35 H35 119.8 . . ?
C37 C36 C35 120.92(19) . . ?
C37 C36 H36 119.5 . . ?
C35 C36 H36 119.5 . . ?
C36 C37 C38 120.50(18) . . ?
C36 C37 H37 119.8 . . ?
C38 C37 H37 119.8 . . ?
N2 C38 C37 119.35(16) . . ?
N2 C38 C33 121.82(17) . . ?
C37 C38 C33 118.82(17) . . ?
N2 C39 C27 119.09(17) . . ?
N2 C39 C31 122.06(17) . . ?
C27 C39 C31 118.85(18) . . ?
C26 C20 C14 120.69(17) . . ?
C26 C20 H20 119.7 . . ?
C14 C20 H20 119.7 . . ?
C20 C14 C15 123.11(18) . . ?
C20 C14 C19 117.72(18) . . ?
C15 C14 C19 119.17(19) . . ?
C16 C15 C14 120.58(19) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C17 120.2(2) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C18 C17 C16 121.3(2) . . ?
C18 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
C17 C18 C19 120.32(19) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
N3 C19 C18 119.18(17) . . ?
N3 C19 C14 122.43(18) . . ?
C18 C19 C14 118.40(18) . . ?
C19 N3 C21 119.08(16) . . ?
N3 C21 C22 119.29(17) . . ?
N3 C21 C26 122.07(17) . . ?
C22 C21 C26 118.64(18) . . ?
C23 C22 C21 120.39(19) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C22 C23 C24 121.1(2) . . ?
C22 C23 H23 119.4 . . ?
C24 C23 H23 119.4 . . ?
C25 C24 C23 120.4(2) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C24 C25 C26 120.67(19) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 H25 119.7 . . ?
C20 C26 C25 123.25(18) . . ?
C20 C26 C21 118.00(18) . . ?
C25 C26 C21 118.74(18) . . ?
C13 C7 C1 120.53(17) . . ?
C13 C7 H7 119.7 . . ?
C1 C7 H7 119.7 . . ?
C7 C1 C2 123.21(18) . . ?
C7 C1 C6 118.02(18) . . ?
C2 C1 C6 118.77(18) . . ?
C3 C2 C1 120.58(19) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 120.3(2) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C5 C4 C3 121.1(2) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C4 C5 C6 120.47(18) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
N4 C6 C5 119.12(17) . . ?
N4 C6 C1 122.11(18) . . ?
C5 C6 C1 118.78(18) . . ?
C6 N4 C8 119.08(16) . . ?
N4 C8 C9 119.31(17) . . ?
N4 C8 C13 122.16(18) . . ?
C9 C8 C13 118.53(18) . . ?
C10 C9 C8 120.66(19) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C9 C10 C11 120.9(2) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C12 C11 C10 120.3(2) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C11 C12 C13 120.84(19) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C7 C13 C12 123.07(18) . . ?
C7 C13 C8 118.09(18) . . ?
C12 C13 C8 118.83(19) . . ?
C54 O1 H1 109.5 . . ?
C58 O2 H2A 109.5 . . ?
O6 N6 O5 122.75(17) . . ?
O6 N6 C53 119.65(16) . . ?
O5 N6 C53 117.60(16) . . ?
C54 C53 C58 122.76(16) . . ?
C54 C53 N6 118.42(15) . . ?
C58 C53 N6 118.75(15) . . ?
O1 C54 C53 117.34(16) . . ?
O1 C54 C55 124.06(17) . . ?
C53 C54 C55 118.57(16) . . ?
C56 C55 C54 118.99(17) . . ?
C56 C55 H55 120.5 . . ?
C54 C55 H55 120.5 . . ?
C57 C56 C55 122.22(18) . . ?
C57 C56 H56 118.9 . . ?
C55 C56 H56 118.9 . . ?
C56 C57 C58 119.72(17) . . ?
C56 C57 H57 120.1 . . ?
C58 C57 H57 120.1 . . ?
O2 C58 C57 124.49(16) . . ?
O2 C58 C53 117.79(16) . . ?
C57 C58 C53 117.71(16) . . ?
C60 O3 H3A 109.5 . . ?
C64 O4 H4A 109.5 . . ?
O11 N5 O8 93.5(8) . . ?
O11 N5 O7 54.7(8) . . ?
O8 N5 O7 122.64(19) . . ?
O11 N5 O12 125.3(6) . . ?
O8 N5 O12 51.5(5) . . ?
O7 N5 O12 105.6(5) . . ?
O11 N5 C59 120.2(5) . . ?
O8 N5 C59 120.36(17) . . ?
O7 N5 C59 116.97(17) . . ?
O12 N5 C59 114.1(4) . . ?
C60 C59 C64 122.66(16) . . ?
C60 C59 N5 118.86(15) . . ?
C64 C59 N5 118.44(16) . . ?
O3 C60 C59 118.15(16) . . ?
O3 C60 C61 123.83(16) . . ?
C59 C60 C61 118.01(16) . . ?
C62 C61 C60 119.63(17) . . ?
C62 C61 H61 120.2 . . ?
C60 C61 H61 120.2 . . ?
C63 C62 C61 121.70(18) . . ?
C63 C62 H62 119.2 . . ?
C61 C62 H62 119.2 . . ?
C62 C63 C64 119.94(17) . . ?
C62 C63 H63 120.0 . . ?
C64 C63 H63 120.0 . . ?
O4 C64 C63 123.84(16) . . ?
O4 C64 C59 118.09(16) . . ?
C63 C64 C59 118.03(16) . . ?
O12 O8 N5 66.7(4) . . ?
O12 O8 O11 96.9(7) . . ?
N5 O8 O11 41.1(4) . . ?
O11 O7 N5 56.8(4) . . ?
O8 O12 N5 61.8(6) . . ?
O7 O11 N5 68.5(8) . . ?
O7 O11 O8 98.7(7) . . ?
N5 O11 O8 45.4(4) . . ?
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
N1 C52 1.348(2) . ?
N1 C40 1.350(3) . ?
C40 C41 1.426(3) . ?
C40 C45 1.435(3) . ?
C41 C42 1.356(3) . ?
C41 H41 0.9300 . ?
C42 C43 1.421(3) . ?
C42 H42 0.9300 . ?
C43 C44 1.354(3) . ?
C43 H43 0.9300 . ?
C44 C45 1.425(3) . ?
C44 H44 0.9300 . ?
C45 C46 1.387(3) . ?
C46 C47 1.398(3) . ?
C46 H46 0.9300 . ?
C47 C48 1.428(3) . ?
C47 C52 1.430(3) . ?
C48 C49 1.362(3) . ?
C48 H48 0.9300 . ?
C49 C50 1.417(3) . ?
C49 H49 0.9300 . ?
C50 C51 1.358(3) . ?
C50 H50 0.9300 . ?
C51 C52 1.425(3) . ?
C51 H51 0.9300 . ?
N2 C38 1.347(2) . ?
N2 C39 1.352(2) . ?
C27 C28 1.357(3) . ?
C27 C39 1.423(3) . ?
C27 H27 0.9300 . ?
C28 C29 1.424(3) . ?
C28 H28 0.9300 . ?
C29 C30 1.348(3) . ?
C29 H29 0.9300 . ?
C30 C31 1.427(3) . ?
C30 H30 0.9300 . ?
C31 C32 1.390(3) . ?
C31 C39 1.431(3) . ?
C32 C33 1.394(3) . ?
C32 H32 0.9300 . ?
C33 C34 1.426(3) . ?
C33 C38 1.438(2) . ?
C34 C35 1.358(3) . ?
C34 H34 0.9300 . ?
C35 C36 1.425(3) . ?
C35 H35 0.9300 . ?
C36 C37 1.356(3) . ?
C36 H36 0.9300 . ?
C37 C38 1.423(3) . ?
C37 H37 0.9300 . ?
C20 C26 1.387(3) . ?
C20 C14 1.393(3) . ?
C20 H20 0.9300 . ?
C14 C15 1.421(3) . ?
C14 C19 1.434(3) . ?
C15 C16 1.361(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.416(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.358(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.428(3) . ?
C18 H18 0.9300 . ?
C19 N3 1.347(2) . ?
N3 C21 1.352(3) . ?
C21 C22 1.422(3) . ?
C21 C26 1.436(3) . ?
C22 C23 1.357(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.420(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.350(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.429(3) . ?
C25 H25 0.9300 . ?
C7 C13 1.386(3) . ?
C7 C1 1.391(3) . ?
C7 H7 0.9300 . ?
C1 C2 1.430(3) . ?
C1 C6 1.435(3) . ?
C2 C3 1.363(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.416(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.363(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.422(3) . ?
C5 H5 0.9300 . ?
C6 N4 1.349(2) . ?
N4 C8 1.350(3) . ?
C8 C9 1.422(3) . ?
C8 C13 1.435(3) . ?
C9 C10 1.362(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.420(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.356(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.427(3) . ?
C12 H12 0.9300 . ?
O1 C54 1.350(2) . ?
O1 H1 0.8200 . ?
O2 C58 1.340(2) . ?
O2 H2A 0.8200 . ?
O5 N6 1.212(2) . ?
O6 N6 1.205(2) . ?
N6 C53 1.465(2) . ?
C53 C54 1.388(2) . ?
C53 C58 1.394(2) . ?
C54 C55 1.391(3) . ?
C55 C56 1.384(3) . ?
C55 H55 0.9300 . ?
C56 C57 1.380(3) . ?
C56 H56 0.9300 . ?
C57 C58 1.393(3) . ?
C57 H57 0.9300 . ?
O3 C60 1.337(2) . ?
O3 H3A 0.8200 . ?
O4 C64 1.341(2) . ?
O4 H4A 0.8200 . ?
N5 O11 1.118(8) . ?
N5 O8 1.210(2) . ?
N5 O7 1.242(3) . ?
N5 O12 1.262(8) . ?
N5 C59 1.467(2) . ?
C59 C60 1.394(2) . ?
C59 C64 1.398(2) . ?
C60 C61 1.396(3) . ?
C61 C62 1.387(3) . ?
C61 H61 0.9300 . ?
C62 C63 1.383(3) . ?
C62 H62 0.9300 . ?
C63 C64 1.390(3) . ?
C63 H63 0.9300 . ?
O8 O12 1.074(12) . ?
O8 O11 1.698(11) . ?
O7 O11 1.090(15) . ?
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
C52 N1 C40 C41 179.26(16) . . . . ?
C52 N1 C40 C45 -1.5(3) . . . . ?
N1 C40 C41 C42 179.34(18) . . . . ?
C45 C40 C41 C42 0.1(3) . . . . ?
C40 C41 C42 C43 0.1(3) . . . . ?
C41 C42 C43 C44 -0.4(3) . . . . ?
C42 C43 C44 C45 0.6(3) . . . . ?
C43 C44 C45 C46 179.82(19) . . . . ?
C43 C44 C45 C40 -0.4(3) . . . . ?
N1 C40 C45 C46 0.6(3) . . . . ?
C41 C40 C45 C46 179.86(17) . . . . ?
N1 C40 C45 C44 -179.19(17) . . . . ?
C41 C40 C45 C44 0.0(3) . . . . ?
C44 C45 C46 C47 -179.50(17) . . . . ?
C40 C45 C46 C47 0.7(3) . . . . ?
C45 C46 C47 C48 179.36(17) . . . . ?
C45 C46 C47 C52 -1.1(3) . . . . ?
C46 C47 C48 C49 179.60(18) . . . . ?
C52 C47 C48 C49 0.1(3) . . . . ?
C47 C48 C49 C50 -0.5(3) . . . . ?
C48 C49 C50 C51 0.5(3) . . . . ?
C49 C50 C51 C52 0.0(3) . . . . ?
C40 N1 C52 C51 -179.49(16) . . . . ?
C40 N1 C52 C47 1.1(3) . . . . ?
C50 C51 C52 N1 -179.79(17) . . . . ?
C50 C51 C52 C47 -0.4(3) . . . . ?
C46 C47 C52 N1 0.2(3) . . . . ?
C48 C47 C52 N1 179.77(16) . . . . ?
C46 C47 C52 C51 -179.22(16) . . . . ?
C48 C47 C52 C51 0.3(3) . . . . ?
C39 C27 C28 C29 -0.2(3) . . . . ?
C27 C28 C29 C30 0.7(3) . . . . ?
C28 C29 C30 C31 -0.8(3) . . . . ?
C29 C30 C31 C32 179.75(19) . . . . ?
C29 C30 C31 C39 0.4(3) . . . . ?
C30 C31 C32 C33 179.15(17) . . . . ?
C39 C31 C32 C33 -1.5(3) . . . . ?
C31 C32 C33 C34 -178.97(17) . . . . ?
C31 C32 C33 C38 1.2(3) . . . . ?
C32 C33 C34 C35 179.69(18) . . . . ?
C38 C33 C34 C35 -0.4(3) . . . . ?
C33 C34 C35 C36 0.5(3) . . . . ?
C34 C35 C36 C37 0.0(3) . . . . ?
C35 C36 C37 C38 -0.6(3) . . . . ?
C39 N2 C38 C37 178.99(16) . . . . ?
C39 N2 C38 C33 -1.8(3) . . . . ?
C36 C37 C38 N2 179.91(17) . . . . ?
C36 C37 C38 C33 0.6(3) . . . . ?
C32 C33 C38 N2 0.5(3) . . . . ?
C34 C33 C38 N2 -179.37(16) . . . . ?
C32 C33 C38 C37 179.75(16) . . . . ?
C34 C33 C38 C37 -0.1(3) . . . . ?
C38 N2 C39 C27 -179.11(16) . . . . ?
C38 N2 C39 C31 1.4(3) . . . . ?
C28 C27 C39 N2 -179.74(18) . . . . ?
C28 C27 C39 C31 -0.2(3) . . . . ?
C32 C31 C39 N2 0.2(3) . . . . ?
C30 C31 C39 N2 179.61(17) . . . . ?
C32 C31 C39 C27 -179.26(17) . . . . ?
C30 C31 C39 C27 0.1(3) . . . . ?
C26 C20 C14 C15 179.46(17) . . . . ?
C26 C20 C14 C19 -0.6(3) . . . . ?
C20 C14 C15 C16 179.43(19) . . . . ?
C19 C14 C15 C16 -0.5(3) . . . . ?
C14 C15 C16 C17 -0.6(3) . . . . ?
C15 C16 C17 C18 1.2(3) . . . . ?
C16 C17 C18 C19 -0.6(3) . . . . ?
C17 C18 C19 N3 179.11(17) . . . . ?
C17 C18 C19 C14 -0.5(3) . . . . ?
C20 C14 C19 N3 1.5(3) . . . . ?
C15 C14 C19 N3 -178.52(17) . . . . ?
C20 C14 C19 C18 -178.86(17) . . . . ?
C15 C14 C19 C18 1.1(3) . . . . ?
C18 C19 N3 C21 179.04(16) . . . . ?
C14 C19 N3 C21 -1.4(3) . . . . ?
C19 N3 C21 C22 -179.72(16) . . . . ?
C19 N3 C21 C26 0.3(3) . . . . ?
N3 C21 C22 C23 179.15(17) . . . . ?
C26 C21 C22 C23 -0.8(3) . . . . ?
C21 C22 C23 C24 0.6(3) . . . . ?
C22 C23 C24 C25 0.7(3) . . . . ?
C23 C24 C25 C26 -1.8(3) . . . . ?
C14 C20 C26 C25 -179.57(17) . . . . ?
C14 C20 C26 C21 -0.4(3) . . . . ?
C24 C25 C26 C20 -179.34(18) . . . . ?
C24 C25 C26 C21 1.5(3) . . . . ?
N3 C21 C26 C20 0.6(3) . . . . ?
C22 C21 C26 C20 -179.39(16) . . . . ?
N3 C21 C26 C25 179.82(16) . . . . ?
C22 C21 C26 C25 -0.2(3) . . . . ?
C13 C7 C1 C2 179.84(17) . . . . ?
C13 C7 C1 C6 -0.5(3) . . . . ?
C7 C1 C2 C3 179.82(19) . . . . ?
C6 C1 C2 C3 0.1(3) . . . . ?
C1 C2 C3 C4 0.9(3) . . . . ?
C2 C3 C4 C5 -1.0(3) . . . . ?
C3 C4 C5 C6 0.1(3) . . . . ?
C4 C5 C6 N4 -179.56(17) . . . . ?
C4 C5 C6 C1 0.9(3) . . . . ?
C7 C1 C6 N4 -0.3(3) . . . . ?
C2 C1 C6 N4 179.46(17) . . . . ?
C7 C1 C6 C5 179.31(17) . . . . ?
C2 C1 C6 C5 -1.0(3) . . . . ?
C5 C6 N4 C8 -178.82(16) . . . . ?
C1 C6 N4 C8 0.7(3) . . . . ?
C6 N4 C8 C9 179.25(16) . . . . ?
C6 N4 C8 C13 -0.5(3) . . . . ?
N4 C8 C9 C10 -179.87(17) . . . . ?
C13 C8 C9 C10 -0.1(3) . . . . ?
C8 C9 C10 C11 -0.1(3) . . . . ?
C9 C10 C11 C12 -0.5(3) . . . . ?
C10 C11 C12 C13 1.2(3) . . . . ?
C1 C7 C13 C12 179.90(17) . . . . ?
C1 C7 C13 C8 0.7(3) . . . . ?
C11 C12 C13 C7 179.40(18) . . . . ?
C11 C12 C13 C8 -1.4(3) . . . . ?
N4 C8 C13 C7 -0.2(3) . . . . ?
C9 C8 C13 C7 -179.95(17) . . . . ?
N4 C8 C13 C12 -179.44(16) . . . . ?
C9 C8 C13 C12 0.8(3) . . . . ?
O6 N6 C53 C54 69.9(2) . . . . ?
O5 N6 C53 C54 -109.5(2) . . . . ?
O6 N6 C53 C58 -113.0(2) . . . . ?
O5 N6 C53 C58 67.6(2) . . . . ?
C58 C53 C54 O1 179.89(17) . . . . ?
N6 C53 C54 O1 -3.1(3) . . . . ?
C58 C53 C54 C55 -2.0(3) . . . . ?
N6 C53 C54 C55 175.02(17) . . . . ?
O1 C54 C55 C56 178.88(19) . . . . ?
C53 C54 C55 C56 0.9(3) . . . . ?
C54 C55 C56 C57 0.9(3) . . . . ?
C55 C56 C57 C58 -1.6(3) . . . . ?
C56 C57 C58 O2 179.09(19) . . . . ?
C56 C57 C58 C53 0.5(3) . . . . ?
C54 C53 C58 O2 -177.42(17) . . . . ?
N6 C53 C58 O2 5.6(3) . . . . ?
C54 C53 C58 C57 1.3(3) . . . . ?
N6 C53 C58 C57 -175.71(17) . . . . ?
O11 N5 C59 C60 -57.5(11) . . . . ?
O8 N5 C59 C60 57.6(3) . . . . ?
O7 N5 C59 C60 -120.4(2) . . . . ?
O12 N5 C59 C60 115.7(7) . . . . ?
O11 N5 C59 C64 120.4(10) . . . . ?
O8 N5 C59 C64 -124.5(2) . . . . ?
O7 N5 C59 C64 57.5(3) . . . . ?
O12 N5 C59 C64 -66.4(7) . . . . ?
C64 C59 C60 O3 179.56(18) . . . . ?
N5 C59 C60 O3 -2.6(3) . . . . ?
C64 C59 C60 C61 -1.9(3) . . . . ?
N5 C59 C60 C61 175.88(17) . . . . ?
O3 C60 C61 C62 179.04(19) . . . . ?
C59 C60 C61 C62 0.6(3) . . . . ?
C60 C61 C62 C63 0.9(3) . . . . ?
C61 C62 C63 C64 -1.2(3) . . . . ?
C62 C63 C64 O4 177.61(19) . . . . ?
C62 C63 C64 C59 0.0(3) . . . . ?
C60 C59 C64 O4 -176.14(17) . . . . ?
N5 C59 C64 O4 6.0(3) . . . . ?
C60 C59 C64 C63 1.7(3) . . . . ?
N5 C59 C64 C63 -176.18(17) . . . . ?
O11 N5 O8 O12 -133.7(8) . . . . ?
O7 N5 O8 O12 -84.1(6) . . . . ?
C59 N5 O8 O12 98.0(5) . . . . ?
O7 N5 O8 O11 49.6(6) . . . . ?
O12 N5 O8 O11 133.7(8) . . . . ?
C59 N5 O8 O11 -128.3(7) . . . . ?
O8 N5 O7 O11 -68.7(7) . . . . ?
O12 N5 O7 O11 -122.6(8) . . . . ?
C59 N5 O7 O11 109.3(6) . . . . ?
O11 O8 O12 N5 -28.6(4) . . . . ?
O11 N5 O12 O8 62.1(13) . . . . ?
O7 N5 O12 O8 119.6(4) . . . . ?
C59 N5 O12 O8 -110.6(4) . . . . ?
N5 O7 O11 O8 34.4(2) . . . . ?
O8 N5 O11 O7 128.2(4) . . . . ?
O12 N5 O11 O7 84.3(11) . . . . ?
C59 N5 O11 O7 -103.3(5) . . . . ?
O7 N5 O11 O8 -128.2(4) . . . . ?
O12 N5 O11 O8 -43.9(9) . . . . ?
C59 N5 O11 O8 128.5(6) . . . . ?
O12 O8 O11 O7 -5.7(7) . . . . ?
N5 O8 O11 O7 -47.7(6) . . . . ?
O12 O8 O11 N5 42.0(7) . . . . ?
