#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/73/4507329.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_4507329
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                 105.111(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   30.181(3)
_cell_length_b                   5.7140(6)
_cell_length_c                   21.6818(18)
_cell_measurement_reflns_used    3154
_cell_measurement_temperature    123.01(10)
_cell_measurement_theta_max      76.9290
_cell_measurement_theta_min      2.8996
_cell_volume                     3609.8(6)
_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
;
SHELXL, 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      123.01(10)
_diffrn_detector_area_resol_mean 10.3953
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details
;
  1 omega -116.00  -28.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  -19.0000  -90.0000 44

  2 omega  -38.00   18.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   37.0000   60.0000 28

  3 omega  -30.00   24.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   30.0000  -60.0000 27

  4 omega   65.00   93.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       43.8187  169.0000 -162.0000 14

  5 omega   88.00  174.00   2.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   61.0000   90.0000 43

  6 omega   38.00   82.00   2.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -30.0000    0.0000 22

  7 omega   46.00   98.00   2.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -45.0000   60.0000 26

  8 omega   91.00  177.00   2.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   45.0000 -180.0000 43

  9 omega  109.00  173.00   2.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  111.0000   30.0000 32

 10 omega   37.00  103.00   2.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -94.0000  -30.0000 33
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0514449000
_diffrn_orient_matrix_UB_12      -0.0070088000
_diffrn_orient_matrix_UB_13      -0.0351463000
_diffrn_orient_matrix_UB_21      -0.0085253000
_diffrn_orient_matrix_UB_22      -0.1729513000
_diffrn_orient_matrix_UB_23      0.0502227000
_diffrn_orient_matrix_UB_31      -0.0089148000
_diffrn_orient_matrix_UB_32      0.2062748000
_diffrn_orient_matrix_UB_33      0.0408153000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_av_unetI/netI     0.0534
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            12636
_diffrn_reflns_theta_full        68.00
_diffrn_reflns_theta_max         69.98
_diffrn_reflns_theta_min         3.03
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.110
_exptl_absorpt_correction_T_max  0.843
_exptl_absorpt_correction_T_min  0.613
_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    1.407
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1604
_exptl_crystal_size_max          0.3834
_exptl_crystal_size_mid          0.1639
_exptl_crystal_size_min          0.091
_refine_diff_density_max         0.781
_refine_diff_density_min         -0.720
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       0.00080(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     546
_refine_ls_number_reflns         6773
_refine_ls_number_restraints     141
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0752
_refine_ls_R_factor_gt           0.0612
_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)+(0.0656P)²+2.5571P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1491
_refine_ls_wR_factor_ref         0.1611
_reflns_number_gt                5400
_reflns_number_total             6773
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg3015282_si_002.cif
_cod_data_source_block           C2-K123_itraconazole-cocrystal
_cod_original_cell_volume        3609.9(6)
_cod_database_code               4507329
#BEGIN Tags that were not found in dictionaries:
_chemical_oxdiff_formula         'C37 H41 Cl2 N8 O6'
_reflns_odcompleteness_completeness 99.59
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.79
#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 1.38571(10) 0.0377(8) 0.97664(17) 0.0604(10) Uani 1 1 d . . .
C2 C 1.42920(12) 0.1035(12) 0.9713(2) 0.0872(16) Uani 1 1 d . . .
H2 H 1.4559(17) 0.023(9) 0.997(2) 0.105 Uiso 1 1 d . . .
C3 C 1.43286(12) 0.2737(11) 0.9281(2) 0.0863(15) Uani 1 1 d . . .
C4 C 1.39484(12) 0.3811(9) 0.8895(2) 0.0708(11) Uani 1 1 d . . .
H4 H 1.3988(15) 0.505(8) 0.858(2) 0.085 Uiso 1 1 d . . .
C5 C 1.35189(10) 0.3148(6) 0.89582(18) 0.0515(8) Uani 1 1 d . . .
H5 H 1.3241(13) 0.391(7) 0.8682(18) 0.062 Uiso 1 1 d . . .
C6 C 1.34615(9) 0.1467(6) 0.93934(15) 0.0458(7) Uani 1 1 d . . .
C7 C 1.29803(9) 0.0977(5) 0.94740(13) 0.0389(6) Uani 1 1 d . . .
C8 C 1.29453(9) 0.2034(7) 1.01116(15) 0.0494(8) Uani 1 1 d . . .
H8A H 1.3144 0.1130 1.0467 0.059 Uiso 1 1 calc R . .
H8B H 1.3061 0.3662 1.0143 0.059 Uiso 1 1 calc R . .
C12 C 1.18675(10) 0.0886(6) 1.03524(14) 0.0472(7) Uani 1 1 d . . .
H12 H 1.1645 -0.0064 1.0470 0.057 Uiso 1 1 calc R . .
C10 C 1.21716(9) 0.3753(6) 1.00275(13) 0.0422(7) Uani 1 1 d . . .
H10 H 1.2228 0.5240 0.9867 0.051 Uiso 1 1 calc R . .
C16 C 1.26906(9) -0.1890(5) 0.87734(13) 0.0374(6) Uani 1 1 d . . .
H16A H 1.2504 -0.3337 0.8702 0.045 Uiso 1 1 calc R . .
H16B H 1.2938 -0.2027 0.8552 0.045 Uiso 1 1 calc R . .
C15 C 1.23962(8) 0.0263(5) 0.85522(12) 0.0310(5) Uani 1 1 d . . .
H15 H 1.2383 0.0635 0.8097 0.037 Uiso 1 1 calc R . .
C18 C 1.19206(8) -0.0047(4) 0.86379(12) 0.0298(5) Uani 1 1 d . . .
H18A H 1.1762 -0.1347 0.8366 0.036 Uiso 1 1 calc R . .
H18B H 1.1937 -0.0425 0.9089 0.036 Uiso 1 1 calc R . .
C20 C 1.12238(8) 0.2125(4) 0.84935(11) 0.0252(5) Uani 1 1 d . . .
C25 C 1.10114(8) 0.0395(4) 0.87610(11) 0.0276(5) Uani 1 1 d . . .
H25 H 1.1180 -0.0945 0.8948 0.033 Uiso 1 1 calc R . .
C24 C 1.05516(8) 0.0617(4) 0.87559(11) 0.0257(5) Uani 1 1 d . . .
H24 H 1.0412 -0.0580 0.8944 0.031 Uiso 1 1 calc R . .
C23 C 1.02886(8) 0.2548(4) 0.84824(10) 0.0221(4) Uani 1 1 d . . .
C22 C 1.05152(8) 0.4265(4) 0.82177(11) 0.0271(5) Uani 1 1 d . . .
H22 H 1.0349 0.5608 0.8027 0.033 Uiso 1 1 calc R . .
C21 C 1.09716(8) 0.4062(4) 0.82252(11) 0.0269(5) Uani 1 1 d . . .
H21 H 1.1115 0.5267 0.8044 0.032 Uiso 1 1 calc R . .
C31 C 0.95702(8) 0.0644(4) 0.85132(11) 0.0252(5) Uani 1 1 d . . .
H31A H 0.9741 -0.0310 0.8879 0.030 Uiso 1 1 calc R . .
H31B H 0.9550 -0.0265 0.8118 0.030 Uiso 1 1 calc R . .
C30 C 0.90890(8) 0.1091(4) 0.85801(11) 0.0246(5) Uani 1 1 d . . .
H30A H 0.8922 -0.0413 0.8553 0.029 Uiso 1 1 calc R . .
H30B H 0.9108 0.1789 0.9004 0.029 Uiso 1 1 calc R . .
C28 C 0.90871(8) 0.4880(4) 0.81317(11) 0.0253(5) Uani 1 1 d . . .
H28A H 0.9122 0.5557 0.8562 0.030 Uiso 1 1 calc R . .
H28B H 0.8915 0.6011 0.7812 0.030 Uiso 1 1 calc R . .
C27 C 0.95555(8) 0.4451(4) 0.80228(11) 0.0250(5) Uani 1 1 d . . .
H27A H 0.9519 0.3819 0.7587 0.030 Uiso 1 1 calc R . .
H27B H 0.9723 0.5954 0.8053 0.030 Uiso 1 1 calc R . .
C32 C 0.83656(8) 0.2867(4) 0.80727(11) 0.0276(5) Uani 1 1 d . . .
C37 C 0.80727(9) 0.1013(5) 0.78244(12) 0.0338(6) Uani 1 1 d . . .
H37 H 0.8193 -0.0334 0.7668 0.041 Uiso 1 1 calc R . .
C36 C 0.76109(9) 0.1095(5) 0.78015(15) 0.0421(7) Uani 1 1 d . . .
H36 H 0.7415 -0.0178 0.7630 0.050 Uiso 1 1 calc R . .
C35 C 0.74379(10) 0.3059(6) 0.80324(15) 0.0451(7) Uani 1 1 d . . .
C34 C 0.77190(10) 0.4908(6) 0.82832(13) 0.0417(7) Uani 1 1 d . . .
H34 H 0.7596 0.6240 0.8442 0.050 Uiso 1 1 calc R . .
C33 C 0.81846(9) 0.4825(5) 0.83034(12) 0.0333(5) Uani 1 1 d . . .
H33 H 0.8379 0.6105 0.8475 0.040 Uiso 1 1 calc R . .
C49 C 0.93642(8) -0.0653(5) 0.49498(11) 0.0295(5) Uani 1 1 d . . .
C48 C 0.98142(8) 0.0639(4) 0.51128(11) 0.0264(5) Uani 1 1 d . . .
H48A H 0.9918 0.0854 0.5582 0.032 Uiso 1 1 calc R . .
H48B H 0.9768 0.2210 0.4914 0.032 Uiso 1 1 calc R . .
N9 N 1.24798(8) 0.2039(5) 1.01821(11) 0.0414(6) Uani 1 1 d . . .
N13 N 1.22905(9) 0.0149(5) 1.03954(12) 0.0493(6) Uani 1 1 d . . .
N11 N 1.17760(8) 0.3092(5) 1.01281(11) 0.0443(6) Uani 1 1 d . . .
N26 N 0.98231(6) 0.2811(3) 0.84889(9) 0.0221(4) Uani 1 1 d . . .
N29 N 0.88343(7) 0.2680(3) 0.80768(9) 0.0235(4) Uani 1 1 d . . .
N38 N 0.69599(9) 0.3173(6) 0.80015(17) 0.0655(9) Uani 1 1 d D . .
N41A N 0.62523(15) 0.1937(8) 0.7982(3) 0.0813(14) Uani 0.75 1 d PDU A 1
N40A N 0.62440(13) 0.4173(8) 0.7743(3) 0.0646(12) Uani 0.75 1 d PDU A 1
C44A C 0.58053(16) 0.5358(11) 0.7511(3) 0.0718(16) Uani 0.75 1 d PDU A 1
H44A H 0.5862 0.7000 0.7392 0.086 Uiso 0.75 1 calc PR A 1
C42A C 0.66765(17) 0.1346(9) 0.8109(3) 0.0714(17) Uani 0.75 1 d PDU A 1
H42A H 0.6787 -0.0161 0.8259 0.086 Uiso 0.75 1 calc PR A 1
C39 C 0.66726(10) 0.5018(7) 0.7755(2) 0.0605(10) Uani 1 1 d D A .
C46A C 0.5772(3) 0.690(2) 0.8510(5) 0.077(2) Uani 0.75 1 d PU A 1
H46A H 0.5595 0.6920 0.8831 0.115 Uiso 0.75 1 calc PR A 1
H46B H 0.5790 0.8492 0.8349 0.115 Uiso 0.75 1 calc PR A 1
H46C H 0.6083 0.6320 0.8705 0.115 Uiso 0.75 1 calc PR A 1
C45A C 0.55529(19) 0.5415(13) 0.7997(4) 0.087(2) Uani 0.75 1 d PU A 1
H45A H 0.5237 0.5983 0.7806 0.104 Uiso 0.75 1 calc PR A 1
H45B H 0.5532 0.3812 0.8161 0.104 Uiso 0.75 1 calc PR A 1
C47A C 0.5512(2) 0.4030(15) 0.6891(4) 0.092(2) Uani 0.75 1 d PU A 1
H47A H 0.5684 0.3999 0.6565 0.137 Uiso 0.75 1 calc PR A 1
H47B H 0.5220 0.4851 0.6722 0.137 Uiso 0.75 1 calc PR A 1
H47C H 0.5451 0.2423 0.7004 0.137 Uiso 0.75 1 calc PR A 1
N41B N 0.6407(4) 0.330(2) 0.8569(8) 0.0813(14) Uani 0.25 1 d PDU A 2
N40B N 0.6329(3) 0.504(2) 0.8129(6) 0.043(2) Uani 0.25 1 d PDU A 2
C44B C 0.5878(3) 0.622(2) 0.7921(6) 0.039(3) Uani 0.25 1 d PDU A 2
H44B H 0.5896 0.7597 0.7643 0.047 Uiso 0.25 1 calc PR A 2
C42B C 0.6777(5) 0.238(3) 0.8502(8) 0.0714(17) Uani 0.25 1 d PDU A 2
H42B H 0.6928 0.1184 0.8784 0.086 Uiso 0.25 1 calc PR A 2
C47B C 0.5885(11) 0.711(9) 0.865(2) 0.077(2) Uani 0.25 1 d PU A 2
H47D H 0.5601 0.7963 0.8637 0.115 Uiso 0.25 1 calc PR A 2
H47E H 0.6149 0.8136 0.8811 0.115 Uiso 0.25 1 calc PR A 2
H47F H 0.5908 0.5745 0.8930 0.115 Uiso 0.25 1 calc PR A 2
C45B C 0.5496(4) 0.432(3) 0.7529(7) 0.058(4) Uani 0.25 1 d PU A 2
H45C H 0.5397 0.3339 0.7845 0.069 Uiso 0.25 1 calc PR A 2
H45D H 0.5223 0.5198 0.7284 0.069 Uiso 0.25 1 calc PR A 2
C46B C 0.5652(8) 0.277(4) 0.7084(12) 0.080(6) Uani 0.25 1 d PU A 2
H46D H 0.5400 0.1721 0.6872 0.119 Uiso 0.25 1 calc PR A 2
H46E H 0.5913 0.1834 0.7321 0.119 Uiso 0.25 1 calc PR A 2
H46F H 0.5745 0.3712 0.6761 0.119 Uiso 0.25 1 calc PR A 2
O17 O 1.28728(6) -0.1434(4) 0.94408(9) 0.0396(5) Uani 1 1 d . . .
O14 O 1.26435(6) 0.2064(3) 0.89729(9) 0.0355(4) Uani 1 1 d . . .
O19 O 1.16758(6) 0.2084(3) 0.84596(8) 0.0304(4) Uani 1 1 d . . .
O50 O 0.93011(7) -0.2531(3) 0.46899(9) 0.0393(5) Uani 1 1 d . . .
O51 O 0.90349(7) 0.0539(4) 0.51201(9) 0.0389(4) Uani 1 1 d . . .
Cl1 Cl 1.38348(3) -0.1804(2) 1.03146(4) 0.0735(3) Uani 1 1 d . . .
Cl2 Cl 1.48722(4) 0.3538(4) 0.92125(9) 0.1442(8) Uani 1 1 d . . .
O43A O 0.6775(6) 0.688(2) 0.7553(6) 0.059(3) Uani 0.75 1 d PD A 1
O43B O 0.674(2) 0.658(6) 0.7421(17) 0.047(6) Uani 0.25 1 d PD A 2
H51 H 0.8786(14) -0.030(7) 0.5043(19) 0.068(12) 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
-1 -3 6 0.1445 -0.9666 -2.9990 6.0027 -0.1402 0.8284 -0.3650
19 1 0 0.0742 19.0018 1.0057 -0.0188 -0.9839 -0.3369 0.0373
-18 -1 4 0.0806 -17.9907 -1.0046 4.0193 0.7913 0.5290 0.1172
-18 0 -2 0.0410 -18.0127 -0.0059 -1.9827 0.9964 0.0550 0.0784
18 0 1 0.0443 18.0100 0.0057 0.9824 -0.9611 -0.1052 -0.1193
-5 4 2 0.1508 -5.0204 3.9988 2.0064 0.1597 -0.5480 0.9515
-7 0 14 0.0819 -6.9655 0.0008 14.0121 -0.1341 0.7630 0.6342
7 0 -14 0.0819 6.9655 -0.0008 -14.0121 0.1341 -0.7630 -0.6342
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 C6 120.6(4) . .
C2 C1 Cl1 117.0(3) . .
C6 C1 Cl1 122.3(3) . .
C1 C2 H2 119(3) . .
C3 C2 C1 119.4(4) . .
C3 C2 H2 121(3) . .
C2 C3 C4 121.8(4) . .
C2 C3 Cl2 119.2(3) . .
C4 C3 Cl2 119.0(4) . .
C3 C4 H4 120(3) . .
C3 C4 C5 118.0(4) . .
C5 C4 H4 122(3) . .
C4 C5 H5 119(2) . .
C6 C5 C4 122.6(3) . .
C6 C5 H5 119(2) . .
C1 C6 C7 122.9(3) . .
C5 C6 C1 117.5(3) . .
C5 C6 C7 119.6(3) . .
C6 C7 C8 108.7(2) . .
O17 C7 C6 112.6(2) . .
O17 C7 C8 111.1(3) . .
O17 C7 O14 106.1(2) . .
O14 C7 C6 110.0(2) . .
O14 C7 C8 108.2(2) . .
C7 C8 H8A 109.0 . .
C7 C8 H8B 109.0 . .
H8A C8 H8B 107.8 . .
N9 C8 C7 113.0(2) . .
N9 C8 H8A 109.0 . .
N9 C8 H8B 109.0 . .
N13 C12 H12 122.4 . .
N13 C12 N11 115.1(3) . .
N11 C12 H12 122.4 . .
N9 C10 H10 124.8 . .
N11 C10 H10 124.8 . .
N11 C10 N9 110.5(3) . .
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 102.1(2) . .
C16 C15 H15 110.7 . .
C18 C15 C16 111.3(2) . .
C18 C15 H15 110.7 . .
O14 C15 C16 102.3(2) . .
O14 C15 H15 110.7 . .
O14 C15 C18 110.97(19) . .
C15 C18 H18A 110.1 . .
C15 C18 H18B 110.1 . .
H18A C18 H18B 108.4 . .
O19 C18 C15 108.0(2) . .
O19 C18 H18A 110.1 . .
O19 C18 H18B 110.1 . .
C25 C20 O19 125.5(2) . .
C21 C20 C25 118.9(2) . .
C21 C20 O19 115.6(2) . .
C20 C25 H25 119.9 . .
C20 C25 C24 120.1(2) . .
C24 C25 H25 119.9 . .
C25 C24 H24 119.0 . .
C25 C24 C23 122.0(2) . .
C23 C24 H24 119.0 . .
C24 C23 C22 116.3(2) . .
C24 C23 N26 122.3(2) . .
C22 C23 N26 121.4(2) . .
C23 C22 H22 119.0 . .
C21 C22 C23 122.0(2) . .
C21 C22 H22 119.0 . .
C20 C21 H21 119.6 . .
C22 C21 C20 120.7(2) . .
C22 C21 H21 119.6 . .
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 112.46(18) . .
C31 C30 H30A 109.4 . .
C31 C30 H30B 109.4 . .
H30A C30 H30B 108.0 . .
N29 C30 C31 111.13(18) . .
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 109.72(18) . .
C28 C27 H27A 109.3 . .
C28 C27 H27B 109.3 . .
H27A C27 H27B 108.0 . .
N26 C27 C28 111.55(18) . .
N26 C27 H27A 109.3 . .
N26 C27 H27B 109.3 . .
C37 C32 N29 118.4(2) . .
C33 C32 C37 118.7(2) . .
C33 C32 N29 122.9(2) . .
C32 C37 H37 119.4 . .
C36 C37 C32 121.3(3) . .
C36 C37 H37 119.4 . .
C37 C36 H36 120.5 . .
C37 C36 C35 119.1(3) . .
C35 C36 H36 120.5 . .
C36 C35 N38 119.4(3) . .
C34 C35 C36 120.9(3) . .
C34 C35 N38 119.7(3) . .
C35 C34 H34 120.0 . .
C35 C34 C33 119.9(3) . .
C33 C34 H34 120.0 . .
C32 C33 C34 120.1(3) . .
C32 C33 H33 119.9 . .
C34 C33 H33 119.9 . .
O50 C49 C48 124.8(2) . .
O50 C49 O51 123.1(2) . .
O51 C49 C48 112.1(2) . .
C49 C48 C48 112.6(2) . 3_756
C49 C48 H48A 109.1 . .
C49 C48 H48B 109.1 . .
C48 C48 H48A 109.1 3_756 .
C48 C48 H48B 109.1 3_756 .
H48A C48 H48B 107.8 . .
C10 N9 C8 127.3(3) . .
C10 N9 N13 110.0(2) . .
N13 N9 C8 122.6(3) . .
C12 N13 N9 101.9(3) . .
C10 N11 C12 102.5(3) . .
C23 N26 C31 116.03(18) . .
C23 N26 C27 115.64(18) . .
C27 N26 C31 111.66(18) . .
C28 N29 C30 108.05(17) . .
C32 N29 C30 112.26(18) . .
C32 N29 C28 115.81(19) . .
C42A N38 C35 127.5(3) . .
C42A N38 C42B 42.3(5) . .
C39 N38 C35 125.3(3) . .
C39 N38 C42A 106.4(3) . .
C39 N38 C42B 102.2(7) . .
C42B N38 C35 122.7(7) . .
C42A N41A N40A 104.1(4) . .
N41A N40A C44A 119.2(4) . .
C39 N40A N41A 113.2(4) . .
C39 N40A C44A 127.6(4) . .
N40A C44A H44A 108.9 . .
N40A C44A C47A 109.0(6) . .
C45A C44A N40A 111.1(6) . .
C45A C44A H44A 108.9 . .
C45A C44A C47A 110.0(5) . .
C47A C44A H44A 108.9 . .
N38 C42A H42A 123.7 . .
N41A C42A N38 112.7(4) . .
N41A C42A H42A 123.7 . .
N38 C39 N40B 104.8(5) . .
N40A C39 N38 103.4(3) . .
N40A C39 N40B 38.7(5) . .
O43A C39 N38 127.8(10) . .
O43A C39 N40A 128.6(10) . .
O43A C39 N40B 117.9(10) . .
O43B C39 N38 128(3) . .
O43B C39 N40A 124(3) . .
O43B C39 N40B 125(3) . .
O43B C39 O43A 15(3) . .
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 109.5 . .
C44A C45A H45B 109.5 . .
C46A C45A C44A 110.9(7) . .
C46A C45A H45A 109.5 . .
C46A C45A H45B 109.5 . .
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 102.6(13) . .
C39 N40B C44B 124.1(9) . .
N41B N40B C39 111.3(9) . .
N41B N40B C44B 121.6(10) . .
N40B C44B H44B 110.4 . .
N40B C44B C47B 93.8(16) . .
N40B C44B C45B 108.7(11) . .
C47B C44B H44B 110.4 . .
C45B C44B H44B 110.4 . .
C45B C44B C47B 121.8(16) . .
N38 C42B H42B 120.6 . .
N41B C42B N38 118.9(14) . .
N41B C42B H42B 120.6 . .
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 108.3 . .
C44B C45B H45D 108.3 . .
H45C C45B H45D 107.4 . .
C46B C45B C44B 115.8(12) . .
C46B C45B H45C 108.3 . .
C46B C45B H45D 108.3 . .
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 104.6(2) . .
C7 O14 C15 108.6(2) . .
C20 O19 C18 116.62(18) . .
C49 O51 H51 109(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.399(5) .
C1 C6 1.402(4) .
C1 Cl1 1.736(4) .
C2 H2 0.96(5) .
C2 C3 1.374(7) .
C3 C4 1.376(6) .
C3 Cl2 1.746(4) .
C4 H4 1.01(5) .
C4 C5 1.391(5) .
C5 H5 1.00(4) .
C5 C6 1.389(5) .
C6 C7 1.533(4) .
C7 C8 1.537(4) .
C7 O17 1.413(4) .
C7 O14 1.422(3) .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C8 N9 1.452(3) .
C12 H12 0.9500 .
C12 N13 1.324(4) .
C12 N11 1.353(4) .
C10 H10 0.9500 .
C10 N9 1.332(4) .
C10 N11 1.323(4) .
C16 H16A 0.9900 .
C16 H16B 0.9900 .
C16 C15 1.520(4) .
C16 O17 1.432(3) .
C15 H15 1.0000 .
C15 C18 1.505(3) .
C15 O14 1.447(3) .
C18 H18A 0.9900 .
C18 H18B 0.9900 .
C18 O19 1.425(3) .
C20 C25 1.385(3) .
C20 C21 1.383(3) .
C20 O19 1.385(3) .
C25 H25 0.9500 .
C25 C24 1.391(3) .
C24 H24 0.9500 .
C24 C23 1.398(3) .
C23 C22 1.401(3) .
C23 N26 1.417(3) .
C22 H22 0.9500 .
C22 C21 1.378(3) .
C21 H21 0.9500 .
C31 H31A 0.9900 .
C31 H31B 0.9900 .
C31 C30 1.518(3) .
C31 N26 1.463(3) .
C30 H30A 0.9900 .
C30 H30B 0.9900 .
C30 N29 1.473(3) .
C28 H28A 0.9900 .
C28 H28B 0.9900 .
C28 C27 1.513(3) .
C28 N29 1.459(3) .
C27 H27A 0.9900 .
C27 H27B 0.9900 .
C27 N26 1.458(3) .
C32 C37 1.395(4) .
C32 C33 1.394(4) .
C32 N29 1.416(3) .
C37 H37 0.9500 .
C37 C36 1.383(4) .
C36 H36 0.9500 .
C36 C35 1.385(5) .
C35 C34 1.375(5) .
C35 N38 1.428(4) .
C34 H34 0.9500 .
C34 C33 1.395(4) .
C33 H33 0.9500 .
C49 C48 1.505(3) .
C49 O50 1.204(3) .
C49 O51 1.334(3) .
C48 C48 1.522(5) 3_756
C48 H48A 0.9900 .
C48 H48B 0.9900 .
N9 N13 1.358(4) .
N38 C42A 1.407(5) .
N38 C39 1.381(4) .
N38 C42B 1.414(16) .
N41A N40A 1.377(6) .
N41A C42A 1.283(6) .
N40A C44A 1.455(6) .
N40A C39 1.375(5) .
C44A H44A 1.0000 .
C44A C45A 1.454(8) .
C44A C47A 1.595(10) .
C42A H42A 0.9500 .
C39 N40B 1.473(11) .
C39 O43A 1.221(8) .
C39 O43B 1.201(16) .
C46A H46A 0.9800 .
C46A H46B 0.9800 .
C46A H46C 0.9800 .
C46A C45A 1.418(11) .
C45A H45A 0.9900 .
C45A H45B 0.9900 .
C47A H47A 0.9800 .
C47A H47B 0.9800 .
C47A H47C 0.9800 .
N41B N40B 1.356(17) .
N41B C42B 1.278(19) .
N40B C44B 1.483(14) .
C44B H44B 1.0000 .
C44B C47B 1.65(4) .
C44B C45B 1.649(18) .
C42B H42B 0.9500 .
C47B H47D 0.9800 .
C47B H47E 0.9800 .
C47B H47F 0.9800 .
C45B H45C 0.9900 .
C45B H45D 0.9900 .
C45B C46B 1.48(2) .
C46B H46D 0.9800 .
C46B H46E 0.9800 .
C46B H46F 0.9800 .
O51 H51 0.87(4) .
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 -0.3(9) .
C1 C2 C3 Cl2 -179.6(4) .
C1 C6 C7 C8 70.1(4) .
C1 C6 C7 O17 -53.4(4) .
C1 C6 C7 O14 -171.5(3) .
C2 C1 C6 C5 2.2(6) .
C2 C1 C6 C7 -174.3(4) .
C2 C3 C4 C5 0.7(8) .
C3 C4 C5 C6 0.3(7) .
C4 C5 C6 C1 -1.7(5) .
C4 C5 C6 C7 174.9(3) .
C5 C6 C7 C8 -106.3(3) .
C5 C6 C7 O17 130.2(3) .
C5 C6 C7 O14 12.0(4) .
C6 C1 C2 C3 -1.3(7) .
C6 C7 C8 N9 169.6(3) .
C6 C7 O17 C16 -86.6(3) .
C6 C7 O14 C15 109.5(2) .
C7 C8 N9 C10 -92.6(4) .
C7 C8 N9 N13 83.9(4) .
C8 C7 O17 C16 151.3(2) .
C8 C7 O14 C15 -131.9(2) .
C8 N9 N13 C12 -177.0(2) .
C10 N9 N13 C12 0.0(3) .
C16 C15 C18 O19 176.4(2) .
C16 C15 O14 C7 -12.1(3) .
C15 C16 O17 C7 -40.6(2) .
C15 C18 O19 C20 178.65(19) .
C18 C15 O14 C7 106.7(2) .
C20 C25 C24 C23 0.4(4) .
C25 C20 C21 C22 -0.6(4) .
C25 C20 O19 C18 8.8(3) .
C25 C24 C23 C22 -0.6(3) .
C25 C24 C23 N26 -178.5(2) .
C24 C23 C22 C21 0.1(3) .
C24 C23 N26 C31 -27.4(3) .
C24 C23 N26 C27 -161.1(2) .
C23 C22 C21 C20 0.5(4) .
C22 C23 N26 C31 154.7(2) .
C22 C23 N26 C27 21.1(3) .
C21 C20 C25 C24 0.2(3) .
C21 C20 O19 C18 -170.2(2) .
C31 C30 N29 C28 -59.4(2) .
C31 C30 N29 C32 171.69(19) .
C30 C31 N26 C23 174.73(18) .
C30 C31 N26 C27 -49.9(2) .
C28 C27 N26 C23 -171.52(18) .
C28 C27 N26 C31 52.9(2) .
C27 C28 N29 C30 62.2(2) .
C27 C28 N29 C32 -170.92(19) .
C32 C37 C36 C35 -0.2(4) .
C37 C32 C33 C34 -0.1(4) .
C37 C32 N29 C30 -75.3(3) .
C37 C32 N29 C28 160.0(2) .
C37 C36 C35 C34 -0.1(4) .
C37 C36 C35 N38 179.0(3) .
C36 C35 C34 C33 0.4(4) .
C36 C35 N38 C42A 38.9(6) .
C36 C35 N38 C39 -129.5(4) .
C36 C35 N38 C42B 90.9(8) .
C35 C34 C33 C32 -0.3(4) .
C35 N38 C42A N41A -173.4(5) .
C35 N38 C39 N40A 171.4(4) .
C35 N38 C39 N40B -148.7(6) .
C35 N38 C39 O43A -3.9(11) .
C35 N38 C39 O43B 16(3) .
C35 N38 C42B N41B 152.9(8) .
C34 C35 N38 C42A -141.9(4) .
C34 C35 N38 C39 49.7(5) .
C34 C35 N38 C42B -89.9(7) .
C33 C32 C37 C36 0.3(4) .
C33 C32 N29 C30 105.0(3) .
C33 C32 N29 C28 -19.8(3) .
N9 C10 N11 C12 0.1(3) .
N13 C12 N11 C10 -0.1(3) .
N11 C12 N13 N9 0.1(3) .
N11 C10 N9 C8 176.8(3) .
N11 C10 N9 N13 0.0(3) .
N26 C23 C22 C21 178.1(2) .
N26 C31 C30 N29 53.8(2) .
N29 C28 C27 N26 -60.0(2) .
N29 C32 C37 C36 -179.4(2) .
N29 C32 C33 C34 179.7(2) .
N38 C35 C34 C33 -178.8(3) .
N38 C39 N40B N41B -0.4(12) .
N38 C39 N40B C44B -161.0(11) .
N41A N40A C44A C45A 55.0(8) .
N41A N40A C44A C47A -66.3(7) .
N41A N40A C39 N38 1.4(7) .
N41A N40A C39 N40B -95.6(9) .
N41A N40A C39 O43A 176.6(10) .
N41A N40A C39 O43B 158(3) .
N40A N41A C42A N38 3.9(6) .
N40A C44A C45A C46A 68.6(9) .
N40A C39 N40B N41B 92.7(13) .
N40A C39 N40B C44B -67.9(11) .
C44A N40A C39 N38 -178.2(6) .
C44A N40A C39 N40B 84.8(9) .
C44A N40A C39 O43A -3.0(13) .
C44A N40A C39 O43B -21(3) .
C42A N38 C39 N40A 0.9(5) .
C42A N38 C39 N40B 40.9(7) .
C42A N38 C39 O43A -174.4(9) .
C42A N38 C39 O43B -155(3) .
C42A N38 C42B N41B -95.5(12) .
C42A N41A N40A C44A 176.3(6) .
C42A N41A N40A C39 -3.3(7) .
C39 N38 C42A N41A -3.2(6) .
C39 N38 C42B N41B 5.6(9) .
C39 N40A C44A C45A -125.3(7) .
C39 N40A C44A C47A 113.3(7) .
C39 N40B C44B C47B -142.6(19) .
C39 N40B C44B C45B 92.0(13) .
C47A C44A C45A C46A -170.6(8) .
N41B N40B C44B C47B 59(2) .
N41B N40B C44B C45B -66.6(17) .
N40B N41B C42B N38 -5.8(12) .
N40B C44B C45B C46B -41.5(19) .
C42B N38 C42A N41A 86.9(11) .
C42B N38 C39 N40A -42.5(7) .
C42B N38 C39 N40B -2.6(8) .
C42B N38 C39 O43A 142.2(12) .
C42B N38 C39 O43B 162(2) .
C42B N41B N40B C39 3.6(12) .
C42B N41B N40B C44B 164.7(12) .
C47B C44B C45B C46B -148(2) .
O17 C7 C8 N9 -66.0(3) .
O17 C7 O14 C15 -12.6(3) .
O17 C16 C15 C18 -86.7(2) .
O17 C16 C15 O14 31.9(2) .
O14 C7 C8 N9 50.1(4) .
O14 C7 O17 C16 33.8(2) .
O14 C15 C18 O19 63.1(2) .
O19 C20 C25 C24 -178.8(2) .
O19 C20 C21 C22 178.5(2) .
O50 C49 C48 C48 2.5(4) 3_756
O51 C49 C48 C48 -176.8(2) 3_756
Cl1 C1 C2 C3 179.3(4) .
Cl1 C1 C6 C5 -178.4(3) .
Cl1 C1 C6 C7 5.1(5) .
Cl2 C3 C4 C5 -180.0(4) .
O43A C39 N40B N41B -149.4(12) .
O43A C39 N40B C44B 50.1(16) .
O43B C39 N40B N41B -165(3) .
O43B C39 N40B C44B 34(3) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139146381
