#------------------------------------------------------------------------------
#$Date: 2024-06-18 00:43:43 +0200 (Tue 18 de Jun de 2024) $
#$Revision: 292436 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/88/7248884.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_7248884
loop_
_publ_author_name
'Kar, Ananya'
'Giri, Lopamudra'
'Kenguva, Gowtham'
'Rekha Rout, Smruti'
'Dandela, Rambabu'
_publ_section_title
;
 Polymorphism, phase transition and physicochemical properties
 investigation of Ensifentrine
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D4CE00410H
_journal_year                    2024
_chemical_formula_moiety         '2(C26 H32 N5 O4), C O, 2(Cl), 4(O)'
_chemical_formula_sum            'C53 H64 Cl2 N10 O13'
_chemical_formula_weight         1120.04
_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   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2024-05-24 deposited with the CCDC.	2024-06-17 downloaded from the CCDC.
;
_cell_angle_alpha                93.64(1)
_cell_angle_beta                 105.06(2)
_cell_angle_gamma                91.16(1)
_cell_formula_units_Z            2
_cell_length_a                   12.371(8)
_cell_length_b                   13.385(7)
_cell_length_c                   17.690(2)
_cell_measurement_reflns_used    5756
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      0.963
_cell_measurement_theta_min      0.955
_cell_volume                     2821(2)
_computing_cell_refinement       'Bruker SHELXL'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 Venture photon 100 CMOS detector'
_diffrn_measurement_method       'Omega and Phi scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1273
_diffrn_reflns_av_unetI/netI     0.1137
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            54109
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.605
_diffrn_reflns_theta_min         2.245
_diffrn_source                   microfocus
_exptl_absorpt_coefficient_mu    0.186
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_description       needle
_exptl_crystal_F_000             1180.0
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_exptl_transmission_factor_max   0.963
_exptl_transmission_factor_min   0.955
_refine_diff_density_max         0.486
_refine_diff_density_min         -0.575
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     728
_refine_ls_number_reflns         13023
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.110
_refine_ls_R_factor_all          0.1833
_refine_ls_R_factor_gt           0.0751
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1000P)²+0.4550P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1888
_refine_ls_wR_factor_ref         0.2536
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5756
_reflns_number_total             13090
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ce00410h2.cif
_cod_data_source_block           datam_a
_cod_database_code               7248884
_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   0.955
_shelx_estimated_absorpt_t_max   0.963
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
Cl1 Cl 0.09786(10) 0.60937(9) 0.42477(6) 0.0656(3) Uani 1 1 d . . . . .
Cl2 Cl 0.45509(12) 0.06574(12) 0.79300(9) 0.0933(5) Uani 1 1 d . . . . .
O11 O -0.1785(2) 0.0818(2) 0.37588(14) 0.0506(7) Uani 1 1 d . . . . .
O10 O -0.1821(2) 0.1165(2) 0.51835(15) 0.0541(7) Uani 1 1 d . . . . .
N8 N 0.4336(2) 0.1444(2) 0.40991(16) 0.0380(7) Uani 1 1 d . . . . .
O12 O 0.5113(2) 0.1141(2) 0.53722(15) 0.0585(8) Uani 1 1 d . . . . .
N9 N 0.3244(2) 0.1348(2) 0.50033(16) 0.0379(7) Uani 1 1 d . . . . .
O13 O 0.9442(3) 0.2196(2) 0.21779(16) 0.0612(8) Uani 1 1 d . . . . .
O7 O 0.7003(2) 0.3225(2) 0.23337(17) 0.0635(8) Uani 1 1 d . . . . .
N10 N 0.3545(3) 0.1870(2) 0.28319(17) 0.0408(7) Uani 1 1 d . . . . .
N7 N 0.9494(3) 0.5634(2) 0.25042(18) 0.0477(8) Uani 1 1 d . . . . .
O9 O 0.5395(3) 0.3969(2) -0.21869(17) 0.0676(8) Uani 1 1 d . . . . .
O4 O 0.5296(2) 0.1735(2) 0.21072(16) 0.0667(8) Uani 1 1 d . . . . .
O6 O 0.4766(2) 0.3684(2) 0.46187(18) 0.0696(9) Uani 1 1 d . . . . .
N3 N 0.6414(3) 0.2946(2) 0.47044(18) 0.0479(8) Uani 1 1 d . . . . .
N5 N 0.9402(3) 0.3886(2) 0.23622(18) 0.0462(8) Uani 1 1 d . . . . .
O8 O 0.5549(3) 0.5540(2) -0.12528(18) 0.0752(9) Uani 1 1 d . . . . .
N1 N 0.7994(3) 0.4095(3) 0.3448(2) 0.0551(9) Uani 1 1 d . . . . .
N6 N 0.8447(3) 0.3024(2) 0.11662(18) 0.0497(8) Uani 1 1 d . . . . .
C7 C 0.1224(3) 0.1399(2) 0.46385(19) 0.0352(8) Uani 1 1 d . . . . .
C9 C -0.0774(3) 0.1076(3) 0.4268(2) 0.0387(8) Uani 1 1 d . . . . .
C12 C 0.2279(3) 0.1477(2) 0.4423(2) 0.0361(8) Uani 1 1 d . . . . .
C14 C 0.3421(3) 0.1671(3) 0.3528(2) 0.0380(8) Uani 1 1 d . . . . .
C4 C -0.0793(3) 0.1254(3) 0.5053(2) 0.0415(9) Uani 1 1 d . . . . .
C13 C 0.2370(3) 0.1670(3) 0.3697(2) 0.0390(8) Uani 1 1 d . . . . .
H13 H 0.173249 0.180239 0.330893 0.047 Uiso 1 1 calc R U . . .
C15 C 0.4286(3) 0.1304(3) 0.4859(2) 0.0420(9) Uani 1 1 d . . . . .
C8 C 0.0216(3) 0.1161(3) 0.4062(2) 0.0377(8) Uani 1 1 d . . . . .
H8 H 0.022167 0.106213 0.353754 0.045 Uiso 1 1 calc R U . . .
C6 C 0.1200(3) 0.1547(3) 0.5413(2) 0.0383(8) Uani 1 1 d . . . . .
C16 C 0.5455(3) 0.1383(3) 0.3950(2) 0.0412(9) Uani 1 1 d . . . . .
H16A H 0.538062 0.101439 0.344744 0.049 Uiso 1 1 calc R U . . .
H16B H 0.592971 0.100782 0.435056 0.049 Uiso 1 1 calc R U . . .
C44 C 0.9153(3) 0.4789(3) 0.2060(2) 0.0435(9) Uani 1 1 d . . . . .
N2 N 0.6180(3) 0.4462(3) 0.2888(2) 0.0702(11) Uani 1 1 d . . . . .
H2A H 0.586729 0.466317 0.241257 0.105 Uiso 1 1 calc R U . . .
H2B H 0.641927 0.499484 0.322199 0.105 Uiso 1 1 calc R U . . .
H2C H 0.567740 0.410677 0.304851 0.105 Uiso 1 1 calc R U . . .
C45 C 0.9353(3) 0.6615(3) 0.2190(2) 0.0433(9) Uani 1 1 d . . . . .
C5 C 0.0186(3) 0.1490(3) 0.5615(2) 0.0415(9) Uani 1 1 d . . . . .
H5 H 0.017377 0.161362 0.613579 0.050 Uiso 1 1 calc R U . . .
O2 O 0.3500(3) 0.4076(3) 0.5701(2) 0.0924(11) Uani 1 1 d . . . . .
C10 C 0.2285(3) 0.1781(3) 0.6015(2) 0.0461(9) Uani 1 1 d . . . . .
H10A H 0.220944 0.162807 0.652833 0.055 Uiso 1 1 calc R U . . .
H10B H 0.248367 0.248837 0.603444 0.055 Uiso 1 1 calc R U . . .
N4 N 0.6269(3) 0.4177(3) 0.5614(2) 0.0676(10) Uani 1 1 d . . . . .
H4A H 0.588011 0.472413 0.564341 0.101 Uiso 1 1 calc R U . . .
H4B H 0.696249 0.435456 0.560486 0.101 Uiso 1 1 calc R U . . .
H4C H 0.629350 0.382883 0.602983 0.101 Uiso 1 1 calc R U . . .
C19 C 0.2677(3) 0.2249(3) 0.2209(2) 0.0423(9) Uani 1 1 d . . . . .
C43 C 0.8538(3) 0.4792(3) 0.1282(2) 0.0471(10) Uani 1 1 d . . . . .
H43 H 0.840890 0.539714 0.104910 0.057 Uiso 1 1 calc R U . . .
C31 C 0.9120(4) 0.2982(3) 0.1909(2) 0.0492(10) Uani 1 1 d . . . . .
C11 C 0.3187(3) 0.1169(3) 0.5809(2) 0.0455(9) Uani 1 1 d . . . . .
H11A H 0.390240 0.135316 0.617821 0.055 Uiso 1 1 calc R U . . .
H11B H 0.302545 0.046346 0.584316 0.055 Uiso 1 1 calc R U . . .
C17 C 0.6025(3) 0.2388(3) 0.3942(2) 0.0449(9) Uani 1 1 d . . . . .
H17A H 0.666191 0.228561 0.372560 0.054 Uiso 1 1 calc R U . . .
H17B H 0.550645 0.279425 0.359226 0.054 Uiso 1 1 calc R U . . .
C52 C 1.0295(3) 0.7108(3) 0.2092(2) 0.0509(10) Uani 1 1 d . . . . .
C42 C 0.8119(3) 0.3917(3) 0.0854(2) 0.0462(9) Uani 1 1 d . . . . .
C20 C 0.2479(3) 0.3265(3) 0.2232(2) 0.0459(9) Uani 1 1 d . . . . .
O3 O 0.1257(3) 0.4191(3) 0.5192(2) 0.1024(12) Uani 1 1 d . . . . .
O5 O 0.6321(3) 0.0794(3) 0.6972(2) 0.1074(13) Uani 1 1 d . . . . .
C28 C 0.7055(4) 0.3890(3) 0.2857(3) 0.0531(10) Uani 1 1 d . . . . .
C46 C 0.8321(4) 0.7042(3) 0.2033(2) 0.0513(10) Uani 1 1 d . . . . .
C24 C 0.2174(3) 0.1605(3) 0.1557(2) 0.0514(10) Uani 1 1 d . . . . .
C41 C 0.7351(3) 0.3889(3) 0.0073(2) 0.0477(10) Uani 1 1 d . . . . .
C40 C 0.6801(3) 0.4757(3) -0.0195(2) 0.0516(10) Uani 1 1 d . . . . .
H40 H 0.689138 0.533772 0.013658 0.062 Uiso 1 1 calc R U . . .
C18 C 0.5771(4) 0.3610(3) 0.4955(2) 0.0508(10) Uani 1 1 d . . . . .
C34 C 0.7196(4) 0.3020(3) -0.0416(2) 0.0529(10) Uani 1 1 d . . . . .
C30 C 0.9851(3) 0.3768(3) 0.3210(2) 0.0511(10) Uani 1 1 d . . . . .
H30A H 1.018684 0.440110 0.347317 0.061 Uiso 1 1 calc R U . . .
H30B H 1.042847 0.327695 0.328752 0.061 Uiso 1 1 calc R U . . .
C23 C 0.1494(4) 0.2027(4) 0.0923(2) 0.0595(11) Uani 1 1 d . . . . .
H23 H 0.114979 0.160615 0.048311 0.071 Uiso 1 1 calc R U . . .
C22 C 0.1292(3) 0.3036(3) 0.0900(2) 0.0536(10) Uani 1 1 d . . . . .
C36 C 0.6028(3) 0.3879(3) -0.1452(2) 0.0529(10) Uani 1 1 d . . . . .
C35 C 0.6527(4) 0.3025(3) -0.1172(2) 0.0560(11) Uani 1 1 d . . . . .
H35 H 0.641306 0.243800 -0.149775 0.067 Uiso 1 1 calc R U . . .
C39 C 0.6137(4) 0.4747(3) -0.0939(2) 0.0559(11) Uani 1 1 d . . . . .
C29 C 0.8922(4) 0.3432(3) 0.3562(2) 0.0534(11) Uani 1 1 d . . . . .
H29A H 0.864350 0.276980 0.333068 0.064 Uiso 1 1 calc R U . . .
H29B H 0.923102 0.338054 0.412076 0.064 Uiso 1 1 calc R U . . .
C21 C 0.1770(3) 0.3627(3) 0.1566(2) 0.0533(10) Uani 1 1 d . . . . .
H21 H 0.161447 0.430443 0.157536 0.064 Uiso 1 1 calc R U . . .
C51 C 1.0174(4) 0.8052(3) 0.1812(2) 0.0617(12) Uani 1 1 d . . . . .
H51 H 1.080251 0.839382 0.174715 0.074 Uiso 1 1 calc R U . . .
C3 C -0.1791(4) 0.0469(3) 0.2984(2) 0.0589(11) Uani 1 1 d . . . . .
H3A H -0.156956 0.100945 0.271784 0.088 Uiso 1 1 calc R U . . .
H3B H -0.253097 0.022267 0.270620 0.088 Uiso 1 1 calc R U . . .
H3C H -0.127549 -0.006130 0.300245 0.088 Uiso 1 1 calc R U . . .
C48 C 0.8254(4) 0.7984(3) 0.1746(3) 0.0644(12) Uani 1 1 d . . . . .
H48 H 0.756384 0.828349 0.162986 0.077 Uiso 1 1 calc R U . . .
C49 C 0.9169(5) 0.8498(3) 0.1626(3) 0.0661(13) Uani 1 1 d . . . . .
C2 C -0.1889(4) 0.1275(4) 0.5980(2) 0.0632(12) Uani 1 1 d . . . . .
H2D H -0.147436 0.076259 0.627143 0.095 Uiso 1 1 calc R U . . .
H2E H -0.265898 0.121592 0.599246 0.095 Uiso 1 1 calc R U . . .
H2F H -0.157999 0.192166 0.621064 0.095 Uiso 1 1 calc R U . . .
C33 C 0.7780(4) 0.2094(3) -0.0113(2) 0.0675(13) Uani 1 1 d . . . . .
H33A H 0.734209 0.150448 -0.037961 0.081 Uiso 1 1 calc R U . . .
H33B H 0.850595 0.207954 -0.022546 0.081 Uiso 1 1 calc R U . . .
C26 C 0.3006(4) 0.3965(3) 0.2921(3) 0.0698(13) Uani 1 1 d . . . . .
H26A H 0.276134 0.377995 0.336687 0.105 Uiso 1 1 calc R U . . .
H26B H 0.279240 0.463547 0.280657 0.105 Uiso 1 1 calc R U . . .
H26C H 0.380653 0.393160 0.303473 0.105 Uiso 1 1 calc R U . . .
C37 C 0.5284(4) 0.3130(4) -0.2751(3) 0.0735(14) Uani 1 1 d . . . . .
H37A H 0.599676 0.301120 -0.285416 0.110 Uiso 1 1 calc R U . . .
H37B H 0.475003 0.327005 -0.322879 0.110 Uiso 1 1 calc R U . . .
H37C H 0.503155 0.254638 -0.254715 0.110 Uiso 1 1 calc R U . . .
C32 C 0.7932(5) 0.2070(3) 0.0756(3) 0.0716(14) Uani 1 1 d . . . . .
H32A H 0.721018 0.195261 0.086128 0.086 Uiso 1 1 calc R U . . .
H32B H 0.840541 0.152331 0.095013 0.086 Uiso 1 1 calc R U . . .
C47 C 0.7303(4) 0.6531(4) 0.2160(3) 0.0721(13) Uani 1 1 d . . . . .
H47A H 0.704004 0.600035 0.175794 0.108 Uiso 1 1 calc R U . . .
H47B H 0.672637 0.700657 0.213782 0.108 Uiso 1 1 calc R U . . .
H47C H 0.748738 0.625855 0.266440 0.108 Uiso 1 1 calc R U . . .
C27 C 0.0630(4) 0.3477(4) 0.0176(3) 0.0758(14) Uani 1 1 d . . . . .
H27A H -0.011831 0.358138 0.021726 0.114 Uiso 1 1 calc R U . . .
H27B H 0.060707 0.302703 -0.027301 0.114 Uiso 1 1 calc R U . . .
H27C H 0.097690 0.410607 0.011938 0.114 Uiso 1 1 calc R U . . .
C25 C 0.2396(5) 0.0508(3) 0.1545(3) 0.0824(15) Uani 1 1 d . . . . .
H25A H 0.187083 0.016233 0.110467 0.124 Uiso 1 1 calc R U . . .
H25B H 0.231633 0.024905 0.202168 0.124 Uiso 1 1 calc R U . . .
H25C H 0.314439 0.041046 0.149949 0.124 Uiso 1 1 calc R U . . .
C53 C 1.1417(4) 0.6643(4) 0.2268(3) 0.0775(14) Uani 1 1 d . . . . .
H53A H 1.141291 0.610865 0.187931 0.116 Uiso 1 1 calc R U . . .
H53B H 1.157237 0.638313 0.277734 0.116 Uiso 1 1 calc R U . . .
H53C H 1.198411 0.714057 0.226168 0.116 Uiso 1 1 calc R U . . .
C38 C 0.5606(5) 0.6440(4) -0.0764(3) 0.0829(16) Uani 1 1 d . . . . .
H38A H 0.533179 0.630341 -0.031933 0.124 Uiso 1 1 calc R U . . .
H38B H 0.515479 0.693178 -0.105716 0.124 Uiso 1 1 calc R U . . .
H38C H 0.636897 0.669006 -0.058676 0.124 Uiso 1 1 calc R U . . .
C50 C 0.9073(6) 0.9521(4) 0.1298(3) 0.103(2) Uani 1 1 d . . . . .
H50A H 0.951598 1.000681 0.168247 0.154 Uiso 1 1 calc R U . . .
H50B H 0.830352 0.970367 0.117021 0.154 Uiso 1 1 calc R U . . .
H50C H 0.933817 0.949993 0.083335 0.154 Uiso 1 1 calc R U . . .
O1 O 0.4461(18) 0.081(2) 1.0016(7) 0.446(16) Uani 0.927(12) 1 d . . P . .
C1 C 0.408(2) -0.0171(17) 0.9504(19) 0.403(15) Uani 1 1 d . . . . .
H111 H 0.423(3) 0.176(3) 0.271(2) 0.051(11) Uiso 1 1 d . . . . .
H112 H 0.798(4) 0.463(4) 0.387(3) 0.094(16) Uiso 1 1 d . . . . .
O113 O 0.413(4) -0.072(3) 1.033(3) 0.07(2) Uiso 0.073(12) 1 d . . P . .
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'
Cl Cl 0.1484 0.1585 '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
C9 O11 C3 117.4(3) . . ?
C4 O10 C2 117.6(3) . . ?
C14 N8 C15 122.3(3) . . ?
C14 N8 C16 121.5(3) . . ?
C15 N8 C16 116.2(3) . . ?
C12 N9 C15 122.8(3) . . ?
C12 N9 C11 120.5(3) . . ?
C15 N9 C11 116.6(3) . . ?
C14 N10 C19 124.6(3) . . ?
C44 N7 C45 122.5(3) . . ?
C36 O9 C37 118.4(3) . . ?
C18 N3 C17 121.2(3) . . ?
C44 N5 C31 122.4(3) . . ?
C44 N5 C30 123.2(3) . . ?
C31 N5 C30 113.9(3) . . ?
C39 O8 C38 118.3(3) . . ?
C28 N1 C29 120.7(4) . . ?
C31 N6 C42 122.0(3) . . ?
C31 N6 C32 117.0(3) . . ?
C42 N6 C32 120.3(3) . . ?
C6 C7 C8 119.1(3) . . ?
C6 C7 C12 120.4(3) . . ?
C8 C7 C12 120.5(3) . . ?
O11 C9 C8 124.9(3) . . ?
O11 C9 C4 115.0(3) . . ?
C8 C9 C4 120.1(3) . . ?
C13 C12 N9 118.7(3) . . ?
C13 C12 C7 124.4(3) . . ?
N9 C12 C7 116.9(3) . . ?
N10 C14 N8 119.0(3) . . ?
N10 C14 C13 122.3(3) . . ?
N8 C14 C13 118.6(3) . . ?
O10 C4 C5 125.6(3) . . ?
O10 C4 C9 114.8(3) . . ?
C5 C4 C9 119.6(3) . . ?
C12 C13 C14 120.5(3) . . ?
O12 C15 N9 121.4(3) . . ?
O12 C15 N8 121.9(3) . . ?
N9 C15 N8 116.7(3) . . ?
C9 C8 C7 120.4(3) . . ?
C7 C6 C5 120.2(3) . . ?
C7 C6 C10 118.0(3) . . ?
C5 C6 C10 121.8(3) . . ?
N8 C16 C17 114.1(3) . . ?
N7 C44 N5 120.3(3) . . ?
N7 C44 C43 121.8(3) . . ?
N5 C44 C43 117.9(3) . . ?
C46 C45 C52 122.1(4) . . ?
C46 C45 N7 120.3(3) . . ?
C52 C45 N7 117.5(4) . . ?
C4 C5 C6 120.5(3) . . ?
C6 C10 C11 109.5(3) . . ?
C20 C19 C24 121.9(3) . . ?
C20 C19 N10 119.0(3) . . ?
C24 C19 N10 118.6(3) . . ?
C42 C43 C44 120.9(3) . . ?
O13 C31 N6 122.3(4) . . ?
O13 C31 N5 120.7(4) . . ?
N6 C31 N5 117.0(3) . . ?
N9 C11 C10 109.7(3) . . ?
N3 C17 C16 115.3(3) . . ?
C51 C52 C45 117.9(4) . . ?
C51 C52 C53 120.1(4) . . ?
C45 C52 C53 121.9(4) . . ?
C43 C42 N6 118.9(4) . . ?
C43 C42 C41 122.8(3) . . ?
N6 C42 C41 118.3(3) . . ?
C19 C20 C21 117.3(3) . . ?
C19 C20 C26 122.8(3) . . ?
C21 C20 C26 120.0(4) . . ?
O7 C28 N2 122.5(4) . . ?
O7 C28 N1 122.4(4) . . ?
N2 C28 N1 115.1(4) . . ?
C45 C46 C48 117.1(4) . . ?
C45 C46 C47 122.7(4) . . ?
C48 C46 C47 120.2(4) . . ?
C23 C24 C19 117.0(4) . . ?
C23 C24 C25 121.9(4) . . ?
C19 C24 C25 121.0(4) . . ?
C34 C41 C40 120.0(4) . . ?
C34 C41 C42 120.1(4) . . ?
C40 C41 C42 119.9(3) . . ?
C39 C40 C41 119.8(4) . . ?
O6 C18 N3 122.5(4) . . ?
O6 C18 N4 121.5(4) . . ?
N3 C18 N4 116.0(4) . . ?
C35 C34 C41 119.4(4) . . ?
C35 C34 C33 121.5(4) . . ?
C41 C34 C33 119.1(4) . . ?
N5 C30 C29 110.2(3) . . ?
C24 C23 C22 123.9(4) . . ?
C21 C22 C23 116.7(4) . . ?
C21 C22 C27 121.0(4) . . ?
C23 C22 C27 122.3(4) . . ?
O9 C36 C35 125.6(4) . . ?
O9 C36 C39 115.2(4) . . ?
C35 C36 C39 119.1(4) . . ?
C36 C35 C34 121.2(4) . . ?
C40 C39 O8 124.6(4) . . ?
C40 C39 C36 120.2(4) . . ?
O8 C39 C36 115.1(4) . . ?
N1 C29 C30 114.0(3) . . ?
C22 C21 C20 123.2(4) . . ?
C49 C51 C52 122.4(4) . . ?
C49 C48 C46 122.8(4) . . ?
C51 C49 C48 117.6(4) . . ?
C51 C49 C50 120.5(5) . . ?
C48 C49 C50 121.9(5) . . ?
C32 C33 C34 111.1(4) . . ?
N6 C32 C33 110.5(3) . . ?
O1 C1 O113 87(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
O11 C9 1.361(4) . ?
O11 C3 1.418(5) . ?
O10 C4 1.355(4) . ?
O10 C2 1.432(5) . ?
N8 C14 1.362(4) . ?
N8 C15 1.386(4) . ?
N8 C16 1.479(4) . ?
O12 C15 1.211(4) . ?
N9 C12 1.379(4) . ?
N9 C15 1.380(5) . ?
N9 C11 1.480(4) . ?
O13 C31 1.214(4) . ?
O7 C28 1.231(5) . ?
N10 C14 1.323(4) . ?
N10 C19 1.450(5) . ?
N7 C44 1.331(4) . ?
N7 C45 1.453(5) . ?
O9 C36 1.346(5) . ?
O9 C37 1.434(5) . ?
O6 C18 1.240(5) . ?
N3 C18 1.335(5) . ?
N3 C17 1.459(5) . ?
N5 C44 1.361(5) . ?
N5 C31 1.394(5) . ?
N5 C30 1.478(5) . ?
O8 C39 1.364(5) . ?
O8 C38 1.427(5) . ?
N1 C28 1.355(5) . ?
N1 C29 1.446(5) . ?
N6 C31 1.366(5) . ?
N6 C42 1.372(5) . ?
N6 C32 1.474(5) . ?
C7 C6 1.380(5) . ?
C7 C8 1.407(5) . ?
C7 C12 1.455(5) . ?
C9 C8 1.370(5) . ?
C9 C4 1.401(5) . ?
C12 C13 1.358(5) . ?
C14 C13 1.408(5) . ?
C4 C5 1.369(5) . ?
C6 C5 1.393(5) . ?
C6 C10 1.494(5) . ?
C16 C17 1.507(5) . ?
C44 C43 1.389(5) . ?
N2 C28 1.349(5) . ?
C45 C46 1.378(6) . ?
C45 C52 1.384(5) . ?
C10 C11 1.503(5) . ?
N4 C18 1.346(5) . ?
C19 C20 1.387(5) . ?
C19 C24 1.392(5) . ?
C43 C42 1.369(5) . ?
C52 C51 1.382(6) . ?
C52 C53 1.498(6) . ?
C42 C41 1.458(5) . ?
C20 C21 1.396(5) . ?
C20 C26 1.484(5) . ?
C46 C48 1.384(6) . ?
C46 C47 1.496(6) . ?
C24 C23 1.377(6) . ?
C24 C25 1.499(6) . ?
C41 C34 1.383(5) . ?
C41 C40 1.405(5) . ?
C40 C39 1.357(6) . ?
C34 C35 1.379(6) . ?
C34 C33 1.505(6) . ?
C30 C29 1.516(6) . ?
C23 C22 1.379(6) . ?
C22 C21 1.366(6) . ?
C22 C27 1.493(6) . ?
C36 C35 1.369(6) . ?
C36 C39 1.410(6) . ?
C51 C49 1.361(7) . ?
C48 C49 1.384(7) . ?
C49 C50 1.516(6) . ?
C33 C32 1.501(6) . ?
O1 C1 1.54(3) . ?
C1 O113 1.66(5) . ?
