#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/73/4507330.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_4507330
loop_
_publ_author_name
Nonappa,
'Lahtinen, Manu'
'Kolehmainen, Erkki'
'Haarala, Jorma'
'Shevchenko, Anna'
_publ_section_title
;
 Evidence of Weak Halogen Bonding: New Insights on Itraconazole and its
 Succinic Acid Cocrystal
;
_journal_issue                   1
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              346
_journal_paper_doi               10.1021/cg3015282
_journal_volume                  13
_journal_year                    2013
_chemical_formula_moiety         'C35 H38 Cl2 N8 O4, C2 H3 O2'
_chemical_formula_sum            'C37 H41 Cl2 N8 O6'
_chemical_formula_weight         764.68
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 104.370(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   30.2048(10)
_cell_length_b                   5.7706(2)
_cell_length_c                   21.9711(10)
_cell_measurement_reflns_used    2482
_cell_measurement_temperature    273(1)
_cell_measurement_theta_max      76.8505
_cell_measurement_theta_min      3.0181
_cell_volume                     3709.7(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      273(1)
_diffrn_detector_area_resol_mean 10.3953
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details
;
  1 omega -108.00  -16.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  -45.0000  120.0000 92

  2 omega -112.00  -23.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  -30.0000   30.0000 89

  3 omega   41.00   94.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -45.0000   90.0000 53

  4 omega   41.00   99.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -45.0000  -90.0000 58

  5 omega   90.00  178.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   45.0000   30.0000 88

  6 omega   38.00  115.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000 -111.0000 -150.0000 77

  7 omega   39.00   90.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -30.0000 -150.0000 51

  8 omega   47.00  137.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -61.0000    0.0000 90
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0135544000
_diffrn_orient_matrix_UB_12      0.0641557000
_diffrn_orient_matrix_UB_13      0.0610398000
_diffrn_orient_matrix_UB_21      -0.0507478000
_diffrn_orient_matrix_UB_22      -0.0367488000
_diffrn_orient_matrix_UB_23      -0.0333665000
_diffrn_orient_matrix_UB_31      0.0039459000
_diffrn_orient_matrix_UB_32      -0.2562714000
_diffrn_orient_matrix_UB_33      0.0201005000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0499
_diffrn_reflns_av_unetI/netI     0.0562
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            12843
_diffrn_reflns_theta_full        70.00
_diffrn_reflns_theta_max         70.00
_diffrn_reflns_theta_min         3.02
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.053
_exptl_absorpt_correction_T_max  0.973
_exptl_absorpt_correction_T_min  0.646
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Analytical numeric absorption correction using a multifaceted crystal
 model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1604
_exptl_crystal_size_max          0.3511
_exptl_crystal_size_mid          0.1937
_exptl_crystal_size_min          0.0164
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       0.00031(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     537
_refine_ls_number_reflns         6966
_refine_ls_number_restraints     191
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0964
_refine_ls_R_factor_gt           0.0579
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0751P)²+0.1445P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1445
_refine_ls_wR_factor_ref         0.1815
_reflns_number_gt                4218
_reflns_number_total             6966
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg3015282_si_002.cif
_cod_data_source_block           C2-K273_itraconazole-cocrystal
_cod_database_code               4507330
#BEGIN Tags that were not found in dictionaries:
_reflns_odcompleteness_completeness 99.41
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
#END Tags that were not found in dictionaries
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.38422(12) 0.9621(10) 0.0266(2) 0.0884(13) Uani 1 1 d . . .
C2 C -0.42763(14) 0.8952(13) 0.0321(3) 0.119(2) Uani 1 1 d . . .
H2 H -0.4536 0.9642 0.0070 0.143 Uiso 1 1 calc R . .
C3 C -0.43157(15) 0.7281(14) 0.0744(3) 0.121(2) Uani 1 1 d . . .
C4 C -0.39395(15) 0.6251(11) 0.1119(3) 0.1097(17) Uani 1 1 d . . .
H4 H -0.3969 0.5147 0.1414 0.132 Uiso 1 1 calc R . .
C5 C -0.35132(13) 0.6880(8) 0.1049(2) 0.0853(12) Uani 1 1 d . . .
H5 H -0.3257 0.6157 0.1299 0.102 Uiso 1 1 calc R . .
C6 C -0.34525(11) 0.8538(7) 0.06248(18) 0.0706(10) Uani 1 1 d . . .
C7 C -0.29698(10) 0.9028(7) 0.05455(17) 0.0632(8) Uani 1 1 d . . .
C8 C -0.29307(11) 0.7997(9) -0.00789(19) 0.0799(11) Uani 1 1 d . . .
H8A H -0.3040 0.6410 -0.0107 0.096 Uiso 1 1 calc R . .
H8B H -0.3127 0.8863 -0.0419 0.096 Uiso 1 1 calc R . .
C12 C -0.18656(15) 0.9148(10) -0.0346(2) 0.0910(13) Uani 1 1 d . . .
H12 H -0.1650 1.0065 -0.0470 0.109 Uiso 1 1 calc R . .
C10 C -0.21602(13) 0.6337(8) -0.0014(2) 0.0799(11) Uani 1 1 d . . .
H10 H -0.2212 0.4897 0.0145 0.096 Uiso 1 1 calc R . .
C16 C -0.26857(12) 1.1865(6) 0.12384(17) 0.0658(9) Uani 1 1 d . . .
H16A H -0.2928 1.2010 0.1454 0.079 Uiso 1 1 calc R . .
H16B H -0.2501 1.3261 0.1306 0.079 Uiso 1 1 calc R . .
C15 C -0.23985(10) 0.9735(6) 0.14524(15) 0.0564(7) Uani 1 1 d . . .
H15 H -0.2393 0.9367 0.1890 0.068 Uiso 1 1 calc R . .
C18 C -0.19191(10) 1.0047(5) 0.13757(15) 0.0552(7) Uani 1 1 d . . .
H18A H -0.1928 1.0438 0.0943 0.066 Uiso 1 1 calc R . .
H18B H -0.1767 1.1295 0.1643 0.066 Uiso 1 1 calc R . .
C20 C -0.12255(9) 0.7916(5) 0.15127(13) 0.0463(6) Uani 1 1 d . . .
C25 C -0.10100(9) 0.9608(5) 0.12563(14) 0.0511(6) Uani 1 1 d . . .
H25 H -0.1173 1.0910 0.1078 0.061 Uiso 1 1 calc R . .
C24 C -0.05522(9) 0.9401(5) 0.12600(13) 0.0480(6) Uani 1 1 d . . .
H24 H -0.0414 1.0571 0.1082 0.058 Uiso 1 1 calc R . .
C23 C -0.02938(9) 0.7491(4) 0.15237(12) 0.0399(5) Uani 1 1 d . . .
C22 C -0.05240(10) 0.5783(5) 0.17774(14) 0.0501(6) Uani 1 1 d . . .
H22 H -0.0364 0.4471 0.1955 0.060 Uiso 1 1 calc R . .
C21 C -0.09785(10) 0.5977(5) 0.17734(14) 0.0514(7) Uani 1 1 d . . .
H21 H -0.1121 0.4806 0.1946 0.062 Uiso 1 1 calc R . .
C31 C 0.04224(9) 0.9363(5) 0.14873(14) 0.0474(6) Uani 1 1 d . . .
H31A H 0.0440 1.0252 0.1867 0.057 Uiso 1 1 calc R . .
H31B H 0.0257 1.0281 0.1134 0.057 Uiso 1 1 calc R . .
C30 C 0.09020(9) 0.8923(5) 0.14173(14) 0.0472(6) Uani 1 1 d . . .
H30A H 0.0886 0.8246 0.1008 0.057 Uiso 1 1 calc R . .
H30B H 0.1065 1.0383 0.1442 0.057 Uiso 1 1 calc R . .
C28 C 0.09020(9) 0.5179(4) 0.18644(13) 0.0455(6) Uani 1 1 d . . .
H28A H 0.1069 0.4089 0.2173 0.055 Uiso 1 1 calc R . .
H28B H 0.0870 0.4513 0.1450 0.055 Uiso 1 1 calc R . .
C27 C 0.04355(9) 0.5601(5) 0.19755(14) 0.0456(6) Uani 1 1 d . . .
H27A H 0.0272 0.4143 0.1948 0.055 Uiso 1 1 calc R . .
H27B H 0.0469 0.6217 0.2395 0.055 Uiso 1 1 calc R . .
C32 C 0.16197(9) 0.7167(5) 0.19141(13) 0.0469(6) Uani 1 1 d . . .
C37 C 0.19133(10) 0.8992(5) 0.21623(16) 0.0581(7) Uani 1 1 d . . .
H37 H 0.1795 1.0293 0.2316 0.070 Uiso 1 1 calc R . .
C36 C 0.23726(11) 0.8915(6) 0.21854(19) 0.0678(9) Uani 1 1 d . . .
H36 H 0.2563 1.0148 0.2351 0.081 Uiso 1 1 calc R . .
C35 C 0.25455(11) 0.6965(7) 0.19576(19) 0.0686(9) Uani 1 1 d . . .
C34 C 0.22673(12) 0.5132(7) 0.17141(18) 0.0682(9) Uani 1 1 d . . .
H34 H 0.2389 0.3829 0.1566 0.082 Uiso 1 1 calc R . .
C33 C 0.18041(11) 0.5234(6) 0.16904(15) 0.0584(7) Uani 1 1 d . . .
H33 H 0.1615 0.3998 0.1523 0.070 Uiso 1 1 calc R . .
C49 C 0.06319(11) 0.0679(6) 0.50519(14) 0.0570(7) Uani 1 1 d . . .
C48 C 0.01870(10) -0.0604(5) 0.48883(14) 0.0522(7) Uani 1 1 d . . .
H48A H 0.0233 -0.2138 0.5074 0.063 Uiso 1 1 calc R . .
H48B H 0.0090 -0.0790 0.4436 0.063 Uiso 1 1 calc R . .
N9 N -0.24688(9) 0.8021(6) -0.01601(15) 0.0724(8) Uani 1 1 d . . .
N13 N -0.22861(12) 0.9879(7) -0.03748(17) 0.0885(10) Uani 1 1 d . . .
N11 N -0.17726(11) 0.6989(8) -0.01245(17) 0.0848(10) Uani 1 1 d . . .
N26 N 0.01717(7) 0.7225(3) 0.15169(10) 0.0401(5) Uani 1 1 d . . .
N29 N 0.11533(7) 0.7349(4) 0.19114(11) 0.0437(5) Uani 1 1 d . . .
N38 N 0.30220(11) 0.6849(6) 0.1980(2) 0.0908(11) Uani 1 1 d DU . .
N41A N 0.37258(18) 0.8069(10) 0.1989(3) 0.1147(19) Uani 0.75 1 d PDU A 1
N40A N 0.37343(17) 0.5854(10) 0.2222(3) 0.0935(17) Uani 0.75 1 d PDU A 1
C44A C 0.4167(2) 0.4645(15) 0.2439(4) 0.103(2) Uani 0.75 1 d PDU A 1
H44A H 0.4107 0.3058 0.2556 0.124 Uiso 0.75 1 calc PR A 1
C42A C 0.3303(2) 0.8638(13) 0.1875(3) 0.102(2) Uani 0.75 1 d PDU A 1
H42A H 0.3194 1.0101 0.1735 0.122 Uiso 0.75 1 calc PR A 1
C39 C 0.33084(12) 0.5019(8) 0.2221(2) 0.0844(12) Uani 1 1 d DU A .
C46A C 0.4212(4) 0.309(3) 0.1476(6) 0.128(4) Uani 0.75 1 d PU A 1
H46A H 0.4381 0.3061 0.1159 0.192 Uiso 0.75 1 calc PR A 1
H46B H 0.3905 0.3588 0.1293 0.192 Uiso 0.75 1 calc PR A 1
H46C H 0.4207 0.1561 0.1648 0.192 Uiso 0.75 1 calc PR A 1
C45A C 0.4413(3) 0.4568(18) 0.1937(5) 0.130(3) Uani 0.75 1 d PU A 1
H45A H 0.4419 0.6107 0.1762 0.156 Uiso 0.75 1 calc PR A 1
H45B H 0.4726 0.4084 0.2114 0.156 Uiso 0.75 1 calc PR A 1
C47A C 0.4461(4) 0.597(2) 0.3048(6) 0.153(4) Uani 0.75 1 d PU A 1
H47A H 0.4748 0.5187 0.3201 0.229 Uiso 0.75 1 calc PR A 1
H47B H 0.4295 0.5973 0.3369 0.229 Uiso 0.75 1 calc PR A 1
H47C H 0.4515 0.7534 0.2939 0.229 Uiso 0.75 1 calc PR A 1
N41B N 0.3583(5) 0.689(3) 0.1461(10) 0.1147(19) Uani 0.25 1 d PDU A 2
N40B N 0.3652(5) 0.509(3) 0.1867(7) 0.067(3) Uani 0.25 1 d PDU A 2
C44B C 0.4104(5) 0.391(3) 0.2062(8) 0.065(3) Uani 0.25 1 d PDU A 2
H44B H 0.4092 0.2505 0.2307 0.078 Uiso 0.25 1 calc PR A 2
C42B C 0.3209(7) 0.778(4) 0.1508(10) 0.102(2) Uani 0.25 1 d PDU A 2
H42B H 0.3067 0.8970 0.1246 0.122 Uiso 0.25 1 calc PR A 2
C47B C 0.4074(15) 0.330(9) 0.1250(19) 0.129(13) Uani 0.25 1 d PU A 2
H47D H 0.4343 0.2460 0.1220 0.194 Uiso 0.25 1 calc PR A 2
H47E H 0.4057 0.4724 0.1021 0.194 Uiso 0.25 1 calc PR A 2
H47F H 0.3808 0.2378 0.1077 0.194 Uiso 0.25 1 calc PR A 2
C45B C 0.4486(6) 0.572(4) 0.2429(11) 0.092(4) Uani 0.25 1 d PU A 2
H45C H 0.4748 0.4837 0.2660 0.110 Uiso 0.25 1 calc PR A 2
H45D H 0.4587 0.6634 0.2118 0.110 Uiso 0.25 1 calc PR A 2
C46B C 0.4358(14) 0.720(6) 0.2835(19) 0.151(13) Uani 0.25 1 d PU A 2
H46D H 0.4609 0.8196 0.3022 0.227 Uiso 0.25 1 calc PR A 2
H46E H 0.4271 0.6323 0.3159 0.227 Uiso 0.25 1 calc PR A 2
H46F H 0.4104 0.8112 0.2613 0.227 Uiso 0.25 1 calc PR A 2
O17 O -0.28653(8) 1.1419(4) 0.05809(12) 0.0674(6) Uani 1 1 d . . .
O14 O -0.26375(7) 0.7945(4) 0.10352(11) 0.0602(5) Uani 1 1 d . . .
O19 O -0.16780(7) 0.7944(4) 0.15442(11) 0.0594(5) Uani 1 1 d . . .
O50 O 0.06879(10) 0.2522(5) 0.53072(13) 0.0817(8) Uani 1 1 d . . .
O51 O 0.09617(9) -0.0471(5) 0.48849(14) 0.0781(7) Uani 1 1 d . . .
Cl1 Cl -0.38189(4) 1.1782(3) -0.02741(6) 0.1174(5) Uani 1 1 d . . .
Cl2 Cl -0.48574(5) 0.6510(5) 0.08088(12) 0.1981(12) Uani 1 1 d . . .
O43A O 0.3203(4) 0.3159(15) 0.2419(3) 0.093(2) Uani 0.75 1 d PDU A 1
O43B O 0.3253(13) 0.359(5) 0.2590(13) 0.093(2) Uani 0.25 1 d PDU A 2
H51 H 0.122(2) 0.035(10) 0.497(3) 0.13(2) 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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
19 0 0 0.0082 18.9999 0.0000 0.0002 -0.2575 -0.9642 0.0750
-19 0 0 0.0082 -18.9999 -0.0000 -0.0002 0.2575 0.9642 -0.0750
-18 0 -2 0.0098 -17.9999 -0.0000 -2.0001 0.1219 0.9802 -0.1112
18 0 2 0.0098 17.9999 0.0000 2.0001 -0.1219 -0.9802 0.1112
7 0 -14 0.0966 7.0003 0.0000 -13.9999 -0.9494 0.1119 -0.2538
-7 0 14 0.0966 -7.0003 -0.0000 13.9999 0.9494 -0.1119 0.2538
-1 -3 6 0.1453 -0.9981 -3.0000 5.9994 0.1873 -0.0393 0.8855
1 3 -6 0.1453 0.9981 3.0000 -5.9994 -0.1873 0.0393 -0.8855
4 -3 -7 0.1588 4.0021 -3.0000 -7.0005 -0.6740 0.1407 0.6439
-4 3 7 0.1588 -4.0021 3.0000 7.0005 0.6740 -0.1407 -0.6439
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
C2 C1 Cl1 117.0(4) . .
C6 C1 C2 120.4(5) . .
C6 C1 Cl1 122.6(3) . .
C1 C2 H2 120.2 . .
C3 C2 C1 119.7(5) . .
C3 C2 H2 120.2 . .
C2 C3 Cl2 118.7(4) . .
C4 C3 C2 121.2(4) . .
C4 C3 Cl2 120.0(5) . .
C3 C4 H4 120.7 . .
C3 C4 C5 118.6(5) . .
C5 C4 H4 120.7 . .
C4 C5 H5 118.6 . .
C6 C5 C4 122.7(4) . .
C6 C5 H5 118.6 . .
C1 C6 C7 123.1(4) . .
C5 C6 C1 117.3(4) . .
C5 C6 C7 119.5(3) . .
C8 C7 C6 108.5(3) . .
O17 C7 C6 112.2(3) . .
O17 C7 C8 111.3(3) . .
O17 C7 O14 106.3(3) . .
O14 C7 C6 110.2(3) . .
O14 C7 C8 108.1(3) . .
C7 C8 H8A 108.9 . .
C7 C8 H8B 108.9 . .
H8A C8 H8B 107.7 . .
N9 C8 C7 113.5(3) . .
N9 C8 H8A 108.9 . .
N9 C8 H8B 108.9 . .
N13 C12 H12 122.4 . .
N13 C12 N11 115.2(4) . .
N11 C12 H12 122.4 . .
N9 C10 H10 124.7 . .
N11 C10 H10 124.7 . .
N11 C10 N9 110.5(4) . .
H16A C16 H16B 109.2 . .
C15 C16 H16A 111.3 . .
C15 C16 H16B 111.3 . .
O17 C16 H16A 111.3 . .
O17 C16 H16B 111.3 . .
O17 C16 C15 102.2(3) . .
C16 C15 H15 110.5 . .
C18 C15 C16 111.2(3) . .
C18 C15 H15 110.5 . .
O14 C15 C16 103.0(3) . .
O14 C15 H15 110.5 . .
O14 C15 C18 110.8(2) . .
C15 C18 H18A 110.0 . .
C15 C18 H18B 110.0 . .
H18A C18 H18B 108.4 . .
O19 C18 C15 108.3(3) . .
O19 C18 H18A 110.0 . .
O19 C18 H18B 110.0 . .
C25 C20 C21 118.9(2) . .
C25 C20 O19 126.0(3) . .
O19 C20 C21 115.1(2) . .
C20 C25 H25 119.6 . .
C20 C25 C24 120.8(3) . .
C24 C25 H25 119.6 . .
C25 C24 H24 119.1 . .
C25 C24 C23 121.8(3) . .
C23 C24 H24 119.1 . .
C24 C23 C22 116.2(2) . .
C24 C23 N26 122.5(2) . .
C22 C23 N26 121.3(2) . .
C23 C22 H22 118.9 . .
C21 C22 C23 122.3(3) . .
C21 C22 H22 118.9 . .
C20 C21 H21 119.9 . .
C22 C21 C20 120.1(3) . .
C22 C21 H21 119.9 . .
H31A C31 H31B 107.8 . .
C30 C31 H31A 109.1 . .
C30 C31 H31B 109.1 . .
N26 C31 H31A 109.1 . .
N26 C31 H31B 109.1 . .
N26 C31 C30 112.5(2) . .
C31 C30 H30A 109.4 . .
C31 C30 H30B 109.4 . .
H30A C30 H30B 108.0 . .
N29 C30 C31 111.0(2) . .
N29 C30 H30A 109.4 . .
N29 C30 H30B 109.4 . .
H28A C28 H28B 108.2 . .
C27 C28 H28A 109.7 . .
C27 C28 H28B 109.7 . .
N29 C28 H28A 109.7 . .
N29 C28 H28B 109.7 . .
N29 C28 C27 110.0(2) . .
C28 C27 H27A 109.4 . .
C28 C27 H27B 109.4 . .
H27A C27 H27B 108.0 . .
N26 C27 C28 111.3(2) . .
N26 C27 H27A 109.4 . .
N26 C27 H27B 109.4 . .
C37 C32 N29 118.8(3) . .
C33 C32 C37 118.1(3) . .
C33 C32 N29 123.1(3) . .
C32 C37 H37 119.1 . .
C36 C37 C32 121.8(3) . .
C36 C37 H37 119.1 . .
C37 C36 H36 120.7 . .
C37 C36 C35 118.7(3) . .
C35 C36 H36 120.7 . .
C36 C35 N38 119.5(4) . .
C34 C35 C36 121.1(3) . .
C34 C35 N38 119.4(4) . .
C35 C34 H34 120.2 . .
C35 C34 C33 119.7(3) . .
C33 C34 H34 120.2 . .
C32 C33 H33 119.7 . .
C34 C33 C32 120.6(3) . .
C34 C33 H33 119.7 . .
O50 C49 C48 124.5(3) . .
O50 C49 O51 123.3(3) . .
O51 C49 C48 112.2(3) . .
C49 C48 C48 113.2(3) . 3_556
C49 C48 H48A 108.9 . .
C49 C48 H48B 108.9 . .
C48 C48 H48A 108.9 3_556 .
C48 C48 H48B 108.9 3_556 .
H48A C48 H48B 107.8 . .
C10 N9 C8 127.0(4) . .
C10 N9 N13 110.1(3) . .
N13 N9 C8 122.8(3) . .
C12 N13 N9 101.6(4) . .
C10 N11 C12 102.6(3) . .
C23 N26 C31 115.9(2) . .
C23 N26 C27 115.8(2) . .
C31 N26 C27 111.9(2) . .
C28 N29 C30 108.3(2) . .
C32 N29 C30 112.3(2) . .
C32 N29 C28 116.0(2) . .
C42A N38 C35 127.5(4) . .
C42A N38 C42B 38.8(7) . .
C39 N38 C35 125.2(3) . .
C39 N38 C42A 106.3(4) . .
C39 N38 C42B 104.3(10) . .
C42B N38 C35 122.9(10) . .
C42A N41A N40A 103.7(5) . .
N41A N40A C44A 120.0(5) . .
C39 N40A N41A 113.2(5) . .
C39 N40A C44A 126.7(5) . .
N40A C44A H44A 109.0 . .
N40A C44A C45A 110.4(7) . .
N40A C44A C47A 108.2(8) . .
C45A C44A H44A 109.0 . .
C45A C44A C47A 111.1(8) . .
C47A C44A H44A 109.0 . .
N38 C42A H42A 123.3 . .
N41A C42A N38 113.4(6) . .
N41A C42A H42A 123.3 . .
N38 C39 N40B 103.7(6) . .
N40A C39 N38 103.3(4) . .
N40A C39 N40B 36.2(5) . .
O43A C39 N38 127.5(7) . .
O43A C39 N40A 129.1(7) . .
O43A C39 N40B 119.9(9) . .
O43B C39 N38 127(2) . .
O43B C39 N40A 121.9(19) . .
O43B C39 N40B 129(2) . .
O43B C39 O43A 21.1(19) . .
H46A C46A H46B 109.5 . .
H46A C46A H46C 109.5 . .
H46B C46A H46C 109.5 . .
C45A C46A H46A 109.5 . .
C45A C46A H46B 109.5 . .
C45A C46A H46C 109.5 . .
C44A C45A H45A 109.4 . .
C44A C45A H45B 109.4 . .
C46A C45A C44A 111.3(9) . .
C46A C45A H45A 109.4 . .
C46A C45A H45B 109.4 . .
H45A C45A H45B 108.0 . .
C44A C47A H47A 109.5 . .
C44A C47A H47B 109.5 . .
C44A C47A H47C 109.5 . .
H47A C47A H47B 109.5 . .
H47A C47A H47C 109.5 . .
H47B C47A H47C 109.5 . .
C42B N41B N40B 104.5(17) . .
C39 N40B C44B 124.2(12) . .
N41B N40B C39 111.4(12) . .
N41B N40B C44B 121.3(13) . .
N40B C44B H44B 112.4 . .
N40B C44B C47B 89.4(17) . .
N40B C44B C45B 110.0(14) . .
C47B C44B H44B 112.4 . .
C45B C44B H44B 112.4 . .
C45B C44B C47B 118(2) . .
N38 C42B H42B 122.1 . .
N41B C42B N38 116(2) . .
N41B C42B H42B 122.1 . .
C44B C47B H47D 109.5 . .
C44B C47B H47E 109.5 . .
C44B C47B H47F 109.5 . .
H47D C47B H47E 109.5 . .
H47D C47B H47F 109.5 . .
H47E C47B H47F 109.5 . .
C44B C45B H45C 108.2 . .
C44B C45B H45D 108.2 . .
H45C C45B H45D 107.3 . .
C46B C45B C44B 117(2) . .
C46B C45B H45C 108.2 . .
C46B C45B H45D 108.2 . .
C45B C46B H46D 109.5 . .
C45B C46B H46E 109.5 . .
C45B C46B H46F 109.5 . .
H46D C46B H46E 109.5 . .
H46D C46B H46F 109.5 . .
H46E C46B H46F 109.5 . .
C7 O17 C16 104.7(3) . .
C7 O14 C15 108.2(2) . .
C20 O19 C18 116.5(2) . .
C49 O51 H51 110(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.401(6) .
C1 C6 1.392(5) .
C1 Cl1 1.734(5) .
C2 H2 0.9300 .
C2 C3 1.365(9) .
C3 C4 1.363(8) .
C3 Cl2 1.735(5) .
C4 H4 0.9300 .
C4 C5 1.382(6) .
C5 H5 0.9300 .
C5 C6 1.380(6) .
C6 C7 1.537(4) .
C7 C8 1.527(5) .
C7 O17 1.413(4) .
C7 O14 1.421(4) .
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C8 N9 1.450(4) .
C12 H12 0.9300 .
C12 N13 1.325(5) .
C12 N11 1.341(6) .
C10 H10 0.9300 .
C10 N9 1.329(5) .
C10 N11 1.309(5) .
C16 H16A 0.9700 .
C16 H16B 0.9700 .
C16 C15 1.511(4) .
C16 O17 1.435(4) .
C15 H15 0.9800 .
C15 C18 1.509(4) .
C15 O14 1.449(4) .
C18 H18A 0.9700 .
C18 H18B 0.9700 .
C18 O19 1.416(4) .
C20 C25 1.370(4) .
C20 C21 1.388(4) .
C20 O19 1.386(3) .
C25 H25 0.9300 .
C25 C24 1.386(4) .
C24 H24 0.9300 .
C24 C23 1.391(4) .
C23 C22 1.399(4) .
C23 N26 1.418(3) .
C22 H22 0.9300 .
C22 C21 1.375(4) .
C21 H21 0.9300 .
C31 H31A 0.9700 .
C31 H31B 0.9700 .
C31 C30 1.516(4) .
C31 N26 1.458(3) .
C30 H30A 0.9700 .
C30 H30B 0.9700 .
C30 N29 1.473(3) .
C28 H28A 0.9700 .
C28 H28B 0.9700 .
C28 C27 1.508(4) .
C28 N29 1.455(3) .
C27 H27A 0.9700 .
C27 H27B 0.9700 .
C27 N26 1.459(3) .
C32 C37 1.397(4) .
C32 C33 1.390(4) .
C32 N29 1.411(3) .
C37 H37 0.9300 .
C37 C36 1.376(4) .
C36 H36 0.9300 .
C36 C35 1.385(5) .
C35 C34 1.374(5) .
C35 N38 1.429(4) .
C34 H34 0.9300 .
C34 C33 1.388(4) .
C33 H33 0.9300 .
C49 C48 1.498(4) .
C49 O50 1.195(4) .
C49 O51 1.322(4) .
C48 C48 1.509(6) 3_556
C48 H48A 0.9700 .
C48 H48B 0.9700 .
N9 N13 1.344(5) .
N38 C42A 1.391(7) .
N38 C39 1.385(5) .
N38 C42B 1.40(2) .
N41A N40A 1.375(8) .
N41A C42A 1.283(8) .
N40A C44A 1.453(8) .
N40A C39 1.373(6) .
C44A H44A 0.9800 .
C44A C45A 1.476(11) .
C44A C47A 1.604(15) .
C42A H42A 0.9300 .
C39 N40B 1.443(14) .
C39 O43A 1.229(7) .
C39 O43B 1.196(17) .
C46A H46A 0.9600 .
C46A H46B 0.9600 .
C46A H46C 0.9600 .
C46A C45A 1.349(16) .
C45A H45A 0.9700 .
C45A H45B 0.9700 .
C47A H47A 0.9600 .
C47A H47B 0.9600 .
C47A H47C 0.9600 .
N41B N40B 1.35(2) .
N41B C42B 1.27(3) .
N40B C44B 1.49(2) .
C44B H44B 0.9800 .
C44B C47B 1.80(5) .
C44B C45B 1.61(3) .
C42B H42B 0.9300 .
C47B H47D 0.9600 .
C47B H47E 0.9600 .
C47B H47F 0.9600 .
C45B H45C 0.9700 .
C45B H45D 0.9700 .
C45B C46B 1.36(5) .
C46B H46D 0.9600 .
C46B H46E 0.9600 .
C46B H46F 0.9600 .
O51 H51 0.89(6) .
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
C46A H46B N41B 0.96 2.21 2.90(2) 127.4
C46B H46F N41A 0.96 1.55 2.37(4) 139.6
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_4
C1 C2 C3 C4 0.2(11) .
C1 C2 C3 Cl2 179.2(5) .
C1 C6 C7 C8 -70.6(5) .
C1 C6 C7 O17 52.9(5) .
C1 C6 C7 O14 171.2(4) .
C2 C1 C6 C5 -2.8(7) .
C2 C1 C6 C7 174.2(5) .
C2 C3 C4 C5 -1.9(10) .
C3 C4 C5 C6 1.2(9) .
C4 C5 C6 C1 1.2(7) .
C4 C5 C6 C7 -176.0(5) .
C5 C6 C7 C8 106.4(4) .
C5 C6 C7 O17 -130.1(4) .
C5 C6 C7 O14 -11.8(5) .
C6 C1 C2 C3 2.2(9) .
C6 C7 C8 N9 -170.6(3) .
C6 C7 O17 C16 87.1(3) .
C6 C7 O14 C15 -108.9(3) .
C7 C8 N9 C10 92.6(5) .
C7 C8 N9 N13 -83.9(5) .
C8 C7 O17 C16 -151.0(3) .
C8 C7 O14 C15 132.6(3) .
C8 N9 N13 C12 177.5(4) .
C10 N9 N13 C12 0.5(5) .
C16 C15 C18 O19 -176.2(3) .
C16 C15 O14 C7 11.3(3) .
C15 C16 O17 C7 39.6(3) .
C15 C18 O19 C20 -179.0(3) .
C18 C15 O14 C7 -107.6(3) .
C20 C25 C24 C23 -0.2(5) .
C25 C20 C21 C22 0.6(5) .
C25 C20 O19 C18 -9.3(4) .
C25 C24 C23 C22 0.7(4) .
C25 C24 C23 N26 178.3(3) .
C24 C23 C22 C21 -0.6(4) .
C24 C23 N26 C31 26.5(4) .
C24 C23 N26 C27 160.6(2) .
C23 C22 C21 C20 -0.1(5) .
C22 C23 N26 C31 -156.0(3) .
C22 C23 N26 C27 -22.0(4) .
C21 C20 C25 C24 -0.5(5) .
C21 C20 O19 C18 170.2(3) .
C31 C30 N29 C28 59.0(3) .
C31 C30 N29 C32 -171.5(2) .
C30 C31 N26 C23 -174.4(2) .
C30 C31 N26 C27 49.9(3) .
C28 C27 N26 C23 171.5(2) .
C28 C27 N26 C31 -52.7(3) .
C27 C28 N29 C30 -62.0(3) .
C27 C28 N29 C32 170.6(2) .
C32 C37 C36 C35 -0.3(5) .
C37 C32 C33 C34 0.0(5) .
C37 C32 N29 C30 75.8(3) .
C37 C32 N29 C28 -158.9(3) .
C37 C36 C35 C34 -0.2(6) .
C37 C36 C35 N38 -179.8(3) .
C36 C35 C34 C33 0.5(6) .
C36 C35 N38 C42A -38.1(7) .
C36 C35 N38 C39 129.5(5) .
C36 C35 N38 C42B -85.7(10) .
C35 C34 C33 C32 -0.4(5) .
C35 N38 C42A N41A 173.3(5) .
C35 N38 C39 N40A -171.5(5) .
C35 N38 C39 N40B 151.3(7) .
C35 N38 C39 O43A 4.8(10) .
C35 N38 C39 O43B -22(2) .
C35 N38 C42B N41B -155.9(8) .
C34 C35 N38 C42A 142.3(5) .
C34 C35 N38 C39 -50.1(6) .
C34 C35 N38 C42B 94.7(9) .
C33 C32 C37 C36 0.4(5) .
C33 C32 N29 C30 -105.3(3) .
C33 C32 N29 C28 20.0(4) .
N9 C10 N11 C12 -0.1(5) .
N13 C12 N11 C10 0.4(5) .
N11 C12 N13 N9 -0.6(5) .
N11 C10 N9 C8 -177.2(3) .
N11 C10 N9 N13 -0.2(5) .
N26 C23 C22 C21 -178.2(3) .
N26 C31 C30 N29 -53.4(3) .
N29 C28 C27 N26 59.7(3) .
N29 C32 C37 C36 179.3(3) .
N29 C32 C33 C34 -178.9(3) .
N38 C35 C34 C33 -179.9(3) .
N38 C39 N40B N41B 2.2(14) .
N38 C39 N40B C44B 162.4(13) .
N41A N40A C44A C45A -55.6(11) .
N41A N40A C44A C47A 66.2(9) .
N41A N40A C39 N38 -0.7(7) .
N41A N40A C39 N40B 94.4(13) .
N41A N40A C39 O43A -176.9(8) .
N41A N40A C39 O43B -152(2) .
N40A N41A C42A N38 -4.1(7) .
N40A C44A C45A C46A -72.0(11) .
N40A C39 N40B N41B -91.6(16) .
N40A C39 N40B C44B 68.5(14) .
C44A N40A C39 N38 179.2(7) .
C44A N40A C39 N40B -85.7(13) .
C44A N40A C39 O43A 3.0(13) .
C44A N40A C39 O43B 28(3) .
C42A N38 C39 N40A -1.7(6) .
C42A N38 C39 N40B -38.9(8) .
C42A N38 C39 O43A 174.6(7) .
C42A N38 C39 O43B 148(2) .
C42A N38 C42B N41B 93.4(16) .
C42A N41A N40A C44A -176.9(7) .
C42A N41A N40A C39 3.0(8) .
C39 N38 C42A N41A 3.8(7) .
C39 N38 C42B N41B -5.0(10) .
C39 N40A C44A C45A 124.5(9) .
C39 N40A C44A C47A -113.7(9) .
C39 N40B C44B C47B 144(2) .
C39 N40B C44B C45B -95.8(17) .
C47A C44A C45A C46A 168.0(10) .
N41B N40B C44B C47B -58(2) .
N41B N40B C44B C45B 62(2) .
N40B N41B C42B N38 6.3(13) .
N40B C44B C45B C46B 40(3) .
C42B N38 C42A N41A -88.8(17) .
C42B N38 C39 N40A 38.6(8) .
C42B N38 C39 N40B 1.3(10) .
C42B N38 C39 O43A -145.2(10) .
C42B N38 C39 O43B -171.9(19) .
C42B N41B N40B C39 -5.1(15) .
C42B N41B N40B C44B -166.0(14) .
C47B C44B C45B C46B 141(3) .
O17 C7 C8 N9 65.4(4) .
O17 C7 O14 C15 13.0(3) .
O17 C16 C15 C18 87.9(3) .
O17 C16 C15 O14 -30.9(3) .
O14 C7 C8 N9 -51.1(5) .
O14 C7 O17 C16 -33.4(3) .
O14 C15 C18 O19 -62.2(3) .
O19 C20 C25 C24 179.1(3) .
O19 C20 C21 C22 -179.0(3) .
O50 C49 C48 C48 -3.2(5) 3_556
O51 C49 C48 C48 176.3(3) 3_556
Cl1 C1 C2 C3 -179.1(5) .
Cl1 C1 C6 C5 178.6(4) .
Cl1 C1 C6 C7 -4.3(6) .
Cl2 C3 C4 C5 179.1(5) .
O43A C39 N40B N41B 151.9(12) .
O43A C39 N40B C44B -47.9(17) .
O43B C39 N40B N41B 175(2) .
O43B C39 N40B C44B -25(3) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139146381
