#------------------------------------------------------------------------------
#$Date: 2021-05-11 05:48:16 +0200 (mar 11 de may de 2021) $
#$Revision: 265084 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/28/7242808.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_7242808
loop_
_publ_author_name
'Drozd, Ksenia V.'
'Manin, Alex N.'
'Voronin, Alexander P.'
'Boycov, Denis'
'Andrei, Churakov'
'Perlovich, German L.'
_publ_section_title
;
 A combined experimental and theoretical study of miconazole salts and
 cocrystals: crystal structures, DFT computations, formation
 thermodynamics and solubility improvement
;
_journal_name_full               'Physical Chemistry Chemical Physics'
_journal_paper_doi               10.1039/D1CP00956G
_journal_year                    2021
_chemical_formula_moiety         '2(C18 H14 Cl4 N2 O), C6 H10 O4'
_chemical_formula_sum            'C42 H38 Cl8 N4 O6'
_chemical_formula_weight         978.36
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2020-11-09 deposited with the CCDC.	2021-05-10 downloaded from the CCDC.
;
_cell_angle_alpha                103.462(3)
_cell_angle_beta                 100.435(3)
_cell_angle_gamma                113.091(2)
_cell_formula_units_Z            2
_cell_length_a                   12.6233(9)
_cell_length_b                   13.3497(9)
_cell_length_c                   16.0081(11)
_cell_measurement_reflns_used    8048
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.068
_cell_measurement_theta_min      2.349
_cell_volume                     2298.7(3)
_computing_cell_refinement       'SAINT (Bruker, 2018)'
_computing_data_collection       'APEX3 (Bruker, 2018)'
_computing_data_reduction        'SAINT (Bruker, 2018)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT (Sheldrick, 2016)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       ω
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_av_unetI/netI     0.0634
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_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       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            33109
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.000
_diffrn_reflns_theta_min         1.373
_exptl_absorpt_coefficient_mu    0.540
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_description       prism
_exptl_crystal_F_000             1004
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_transmission_factor_max   0.8622
_exptl_transmission_factor_min   0.8116
_refine_diff_density_max         0.513
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     549
_refine_ls_number_reflns         11091
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0784
_refine_ls_R_factor_gt           0.0427
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0445P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0993
_refine_ls_wR_factor_ref         0.1110
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7257
_reflns_number_total             11091
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cp00956g2.cif
_cod_data_source_block           a_sq
_cod_database_code               7242808
_shelx_shelxl_version_number     2016/6
_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   0.900
_shelx_estimated_absorpt_t_max   0.948
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
Cl11 Cl 0.13295(6) -0.44192(5) 0.35044(4) 0.03996(16) Uani 1 1 d . . . . .
Cl12 Cl 0.15484(6) -0.57719(5) 0.63972(4) 0.03619(15) Uani 1 1 d . . . . .
Cl13 Cl -0.17746(5) -0.18592(4) 0.54687(4) 0.03102(14) Uani 1 1 d . . . . .
Cl14 Cl 0.02297(5) 0.24998(5) 0.77397(4) 0.03443(15) Uani 1 1 d . . . . .
N11 N 0.35821(14) -0.07232(14) 0.42050(11) 0.0216(4) Uani 1 1 d . . . . .
N12 N 0.38412(15) 0.07197(15) 0.36909(12) 0.0252(4) Uani 1 1 d . . . . .
O1 O 0.19221(12) -0.10738(11) 0.53498(9) 0.0219(3) Uani 1 1 d . . . . .
C11 C 0.20771(17) -0.19833(16) 0.48050(13) 0.0204(4) Uani 1 1 d . . . . .
H11 H 0.150826 -0.229700 0.418034 0.024 Uiso 1 1 calc R U . . .
C12 C 0.33768(17) -0.14385(17) 0.47856(13) 0.0227(5) Uani 1 1 d . . . . .
H12A H 0.391317 -0.095510 0.540760 0.027 Uiso 1 1 calc R U . . .
H12B H 0.360503 -0.206080 0.457408 0.027 Uiso 1 1 calc R U . . .
C13 C 0.3743(2) -0.10321(19) 0.33757(14) 0.0296(5) Uani 1 1 d . . . . .
H13 H 0.373947 -0.173734 0.307602 0.036 Uiso 1 1 calc R U . . .
C14 C 0.39066(19) -0.01374(18) 0.30672(14) 0.0296(5) Uani 1 1 d . . . . .
H14 H 0.404492 -0.010714 0.250763 0.036 Uiso 1 1 calc R U . . .
C15 C 0.36511(17) 0.03416(18) 0.43675(14) 0.0242(5) Uani 1 1 d . . . . .
H15 H 0.357312 0.076369 0.489932 0.029 Uiso 1 1 calc R U . . .
C21 C 0.18929(17) -0.29524(16) 0.51928(13) 0.0190(4) Uani 1 1 d . . . . .
C22 C 0.15846(18) -0.40713(17) 0.46610(13) 0.0234(5) Uani 1 1 d . . . . .
C23 C 0.14814(18) -0.49441(17) 0.50203(13) 0.0254(5) Uani 1 1 d . . . . .
H23 H 0.127626 -0.569940 0.464394 0.031 Uiso 1 1 calc R U . . .
C24 C 0.16837(19) -0.46872(17) 0.59350(14) 0.0248(5) Uani 1 1 d . . . . .
C25 C 0.19821(19) -0.35911(18) 0.64896(14) 0.0287(5) Uani 1 1 d . . . . .
H25 H 0.211261 -0.342785 0.712009 0.034 Uiso 1 1 calc R U . . .
C26 C 0.20879(18) -0.27344(17) 0.61131(13) 0.0245(5) Uani 1 1 d . . . . .
H26 H 0.229903 -0.197950 0.649368 0.029 Uiso 1 1 calc R U . . .
C31 C 0.06147(17) -0.04115(17) 0.59342(13) 0.0205(4) Uani 1 1 d . . . . .
C32 C 0.16152(19) 0.06483(17) 0.64153(14) 0.0258(5) Uani 1 1 d . . . . .
H32 H 0.238494 0.076294 0.635365 0.031 Uiso 1 1 calc R U . . .
C33 C 0.15156(19) 0.15448(18) 0.69845(14) 0.0278(5) Uani 1 1 d . . . . .
H33 H 0.220821 0.226458 0.731103 0.033 Uiso 1 1 calc R U . . .
C34 C 0.03967(19) 0.13720(17) 0.70671(13) 0.0236(5) Uani 1 1 d . . . . .
C35 C -0.06212(19) 0.03292(17) 0.66151(13) 0.0242(5) Uani 1 1 d . . . . .
H35 H -0.138592 0.021500 0.668806 0.029 Uiso 1 1 calc R U . . .
C36 C -0.04913(18) -0.05458(17) 0.60512(13) 0.0221(4) Uani 1 1 d . . . . .
C37 C 0.06871(17) -0.13871(16) 0.53011(13) 0.0214(4) Uani 1 1 d . . . . .
H37A H 0.034410 -0.209120 0.546698 0.026 Uiso 1 1 calc R U . . .
H37B H 0.021188 -0.155590 0.467729 0.026 Uiso 1 1 calc R U . . .
Cl21 Cl 0.85718(5) 1.43893(4) 0.14680(3) 0.02791(13) Uani 1 1 d . . . . .
Cl22 Cl 0.85501(5) 1.58319(4) -0.13931(3) 0.02874(13) Uani 1 1 d . . . . .
Cl23 Cl 1.19240(4) 1.19600(4) -0.03585(4) 0.03076(14) Uani 1 1 d . . . . .
Cl24 Cl 1.00570(5) 0.76335(4) -0.26793(3) 0.02972(13) Uani 1 1 d . . . . .
N21 N 0.64413(14) 1.05829(14) 0.06003(11) 0.0195(4) Uani 1 1 d . . . . .
N22 N 0.59967(15) 0.89118(15) 0.08175(12) 0.0251(4) Uani 1 1 d . . . . .
O2 O 0.81862(11) 1.11206(11) -0.03894(9) 0.0203(3) Uani 1 1 d . . . . .
C41 C 0.80182(17) 1.20139(16) 0.01673(12) 0.0177(4) Uani 1 1 d . . . . .
H41 H 0.857240 1.231314 0.079582 0.021 Uiso 1 1 calc R U . . .
C42 C 0.67115(17) 1.14539(16) 0.01577(13) 0.0200(4) Uani 1 1 d . . . . .
H42A H 0.651217 1.206324 0.045960 0.024 Uiso 1 1 calc R U . . .
H42B H 0.618505 1.108840 -0.047613 0.024 Uiso 1 1 calc R U . . .
C43 C 0.63500(18) 1.07364(18) 0.14606(14) 0.0255(5) Uani 1 1 d . . . . .
H43 H 0.645722 1.142713 0.188166 0.031 Uiso 1 1 calc R U . . .
C44 C 0.60766(18) 0.97047(19) 0.15867(15) 0.0272(5) Uani 1 1 d . . . . .
H44 H 0.595805 0.955040 0.212161 0.033 Uiso 1 1 calc R U . . .
C45 C 0.62188(17) 0.94713(17) 0.02407(14) 0.0223(5) Uani 1 1 d . . . . .
H45 H 0.622201 0.913664 -0.035095 0.027 Uiso 1 1 calc R U . . .
C51 C 0.82054(16) 1.29955(16) -0.02041(13) 0.0180(4) Uani 1 1 d . . . . .
C52 C 0.81085(18) 1.28189(17) -0.11106(13) 0.0231(5) Uani 1 1 d . . . . .
H52 H 0.796341 1.208436 -0.148729 0.028 Uiso 1 1 calc R U . . .
C53 C 0.82167(18) 1.36801(17) -0.14829(13) 0.0249(5) Uani 1 1 d . . . . .
H53 H 0.815748 1.354287 -0.210308 0.030 Uiso 1 1 calc R U . . .
C54 C 0.84124(18) 1.47429(17) -0.09341(13) 0.0209(4) Uani 1 1 d . . . . .
C55 C 0.85182(17) 1.49645(17) -0.00290(13) 0.0209(4) Uani 1 1 d . . . . .
H55 H 0.865304 1.569781 0.034242 0.025 Uiso 1 1 calc R U . . .
C56 C 0.84227(17) 1.40891(17) 0.03239(12) 0.0188(4) Uani 1 1 d . . . . .
C61 C 0.95418(18) 1.04835(17) -0.09222(13) 0.0190(4) Uani 1 1 d . . . . .
C62 C 0.85570(18) 0.94268(17) -0.14477(13) 0.0225(5) Uani 1 1 d . . . . .
H62 H 0.776837 0.930016 -0.142810 0.027 Uiso 1 1 calc R U . . .
C63 C 0.87060(18) 0.85559(17) -0.19991(14) 0.0248(5) Uani 1 1 d . . . . .
H63 H 0.802608 0.783954 -0.235727 0.030 Uiso 1 1 calc R U . . .
C64 C 0.98474(18) 0.87409(17) -0.20215(13) 0.0209(4) Uani 1 1 d . . . . .
C65 C 1.08514(18) 0.97837(17) -0.15278(13) 0.0216(4) Uani 1 1 d . . . . .
H65 H 1.163531 0.991130 -0.156156 0.026 Uiso 1 1 calc R U . . .
C66 C 1.06728(17) 1.06361(16) -0.09819(13) 0.0199(4) Uani 1 1 d . . . . .
C67 C 0.94299(17) 1.14390(16) -0.03000(13) 0.0201(4) Uani 1 1 d . . . . .
H67A H 0.986967 1.159248 0.033043 0.024 Uiso 1 1 calc R U . . .
H67B H 0.979423 1.215449 -0.044787 0.024 Uiso 1 1 calc R U . . .
O71 O 0.43366(16) 0.26634(14) 0.33720(12) 0.0426(4) Uani 1 1 d . . . . .
H71 H 0.420(3) 0.186(3) 0.354(2) 0.118(13) Uiso 1 1 d . . . . .
O72 O 0.46269(14) 0.18248(13) 0.21114(11) 0.0366(4) Uani 1 1 d . . . . .
O73 O 0.5188(2) 0.72972(17) 0.20219(16) 0.0747(7) Uani 1 1 d . . . . .
O74 O 0.52384(16) 0.67392(15) 0.06182(13) 0.0490(5) Uani 1 1 d . . . . .
H74 H 0.546(2) 0.756(2) 0.0687(18) 0.071(9) Uiso 1 1 d . . . . .
C71 C 0.46270(19) 0.26530(19) 0.26235(17) 0.0311(5) Uani 1 1 d . . . . .
C76 C 0.5032(2) 0.6540(2) 0.1352(2) 0.0452(7) Uani 1 1 d . . . . .
C73 C 0.5336(2) 0.38581(19) 0.16335(18) 0.0405(6) Uani 1 1 d . . . . .
H73A H 0.466586 0.327053 0.109149 0.049 Uiso 1 1 calc R U . . .
H73B H 0.602856 0.367774 0.166741 0.049 Uiso 1 1 calc R U . . .
C72 C 0.4939(2) 0.37922(19) 0.24601(18) 0.0439(7) Uani 1 1 d . . . . .
H72A H 0.422266 0.393740 0.240570 0.053 Uiso 1 1 calc R U . . .
H72B H 0.559385 0.441749 0.299338 0.053 Uiso 1 1 calc R U . . .
C74 C 0.5703(2) 0.5051(2) 0.15410(19) 0.0434(7) Uani 1 1 d . . . . .
H74A H 0.611838 0.510900 0.107267 0.052 Uiso 1 1 calc R U . . .
H74B H 0.628306 0.564691 0.211898 0.052 Uiso 1 1 calc R U . . .
C75 C 0.4611(2) 0.5293(2) 0.1286(2) 0.0498(7) Uani 1 1 d . . . . .
H75A H 0.409818 0.478693 0.066297 0.060 Uiso 1 1 calc R U . . .
H75B H 0.411802 0.511683 0.169660 0.060 Uiso 1 1 calc R U . . .
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'
Cl Cl 0.1484 0.1585 '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
C15 N11 C13 106.88(17) . . ?
C15 N11 C12 127.86(17) . . ?
C13 N11 C12 125.26(17) . . ?
C15 N12 C14 106.14(18) . . ?
C11 O1 C37 112.84(14) . . ?
O1 C11 C21 112.49(15) . . ?
O1 C11 C12 105.79(15) . . ?
C21 C11 C12 108.77(15) . . ?
O1 C11 H11 109.9 . . ?
C21 C11 H11 109.9 . . ?
C12 C11 H11 109.9 . . ?
N11 C12 C11 113.86(16) . . ?
N11 C12 H12A 108.8 . . ?
C11 C12 H12A 108.8 . . ?
N11 C12 H12B 108.8 . . ?
C11 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
C14 C13 N11 106.69(19) . . ?
C14 C13 H13 126.7 . . ?
N11 C13 H13 126.7 . . ?
C13 C14 N12 109.22(19) . . ?
C13 C14 H14 125.4 . . ?
N12 C14 H14 125.4 . . ?
N12 C15 N11 111.07(19) . . ?
N12 C15 H15 124.5 . . ?
N11 C15 H15 124.5 . . ?
C26 C21 C22 117.21(18) . . ?
C26 C21 C11 120.45(17) . . ?
C22 C21 C11 122.26(17) . . ?
C23 C22 C21 122.45(18) . . ?
C23 C22 Cl11 117.25(15) . . ?
C21 C22 Cl11 120.30(15) . . ?
C24 C23 C22 118.25(18) . . ?
C24 C23 H23 120.9 . . ?
C22 C23 H23 120.9 . . ?
C23 C24 C25 121.40(19) . . ?
C23 C24 Cl12 118.95(16) . . ?
C25 C24 Cl12 119.66(16) . . ?
C24 C25 C26 119.09(19) . . ?
C24 C25 H25 120.5 . . ?
C26 C25 H25 120.5 . . ?
C25 C26 C21 121.60(18) . . ?
C25 C26 H26 119.2 . . ?
C21 C26 H26 119.2 . . ?
C32 C31 C36 117.36(19) . . ?
C32 C31 C37 122.80(18) . . ?
C36 C31 C37 119.84(18) . . ?
C31 C32 C33 121.5(2) . . ?
C31 C32 H32 119.3 . . ?
C33 C32 H32 119.3 . . ?
C34 C33 C32 118.8(2) . . ?
C34 C33 H33 120.6 . . ?
C32 C33 H33 120.6 . . ?
C33 C34 C35 121.89(19) . . ?
C33 C34 Cl14 119.98(16) . . ?
C35 C34 Cl14 118.12(16) . . ?
C34 C35 C36 117.81(19) . . ?
C34 C35 H35 121.1 . . ?
C36 C35 H35 121.1 . . ?
C35 C36 C31 122.61(19) . . ?
C35 C36 Cl13 118.09(16) . . ?
C31 C36 Cl13 119.31(15) . . ?
O1 C37 C31 109.30(16) . . ?
O1 C37 H37A 109.8 . . ?
C31 C37 H37A 109.8 . . ?
O1 C37 H37B 109.8 . . ?
C31 C37 H37B 109.8 . . ?
H37A C37 H37B 108.3 . . ?
C45 N21 C43 107.10(17) . . ?
C45 N21 C42 126.58(16) . . ?
C43 N21 C42 126.32(17) . . ?
C45 N22 C44 105.79(17) . . ?
C67 O2 C41 112.35(14) . . ?
O2 C41 C51 112.11(15) . . ?
O2 C41 C42 105.53(15) . . ?
C51 C41 C42 108.23(15) . . ?
O2 C41 H41 110.3 . . ?
C51 C41 H41 110.3 . . ?
C42 C41 H41 110.3 . . ?
N21 C42 C41 113.96(15) . . ?
N21 C42 H42A 108.8 . . ?
C41 C42 H42A 108.8 . . ?
N21 C42 H42B 108.8 . . ?
C41 C42 H42B 108.8 . . ?
H42A C42 H42B 107.7 . . ?
C44 C43 N21 106.27(18) . . ?
C44 C43 H43 126.9 . . ?
N21 C43 H43 126.9 . . ?
C43 C44 N22 109.58(19) . . ?
C43 C44 H44 125.2 . . ?
N22 C44 H44 125.2 . . ?
N22 C45 N21 111.26(18) . . ?
N22 C45 H45 124.4 . . ?
N21 C45 H45 124.4 . . ?
C52 C51 C56 116.93(18) . . ?
C52 C51 C41 120.49(17) . . ?
C56 C51 C41 122.50(17) . . ?
C53 C52 C51 122.10(18) . . ?
C53 C52 H52 118.9 . . ?
C51 C52 H52 119.0 . . ?
C54 C53 C52 118.71(18) . . ?
C54 C53 H53 120.6 . . ?
C52 C53 H53 120.6 . . ?
C55 C54 C53 121.52(18) . . ?
C55 C54 Cl22 119.30(15) . . ?
C53 C54 Cl22 119.18(15) . . ?
C54 C55 C56 118.25(17) . . ?
C54 C55 H55 120.9 . . ?
C56 C55 H55 120.9 . . ?
C55 C56 C51 122.47(17) . . ?
C55 C56 Cl21 117.56(14) . . ?
C51 C56 Cl21 119.97(15) . . ?
C66 C61 C62 117.43(18) . . ?
C66 C61 C67 119.43(18) . . ?
C62 C61 C67 123.14(18) . . ?
C63 C62 C61 121.19(19) . . ?
C63 C62 H62 119.4 . . ?
C61 C62 H62 119.4 . . ?
C64 C63 C62 119.18(19) . . ?
C64 C63 H63 120.4 . . ?
C62 C63 H63 120.4 . . ?
C63 C64 C65 121.85(18) . . ?
C63 C64 Cl24 119.75(16) . . ?
C65 C64 Cl24 118.40(15) . . ?
C64 C65 C66 117.55(18) . . ?
C64 C65 H65 121.2 . . ?
C66 C65 H65 121.2 . . ?
C65 C66 C61 122.77(18) . . ?
C65 C66 Cl23 118.34(15) . . ?
C61 C66 Cl23 118.88(15) . . ?
O2 C67 C61 109.71(15) . . ?
O2 C67 H67A 109.7 . . ?
C61 C67 H67A 109.7 . . ?
O2 C67 H67B 109.7 . . ?
C61 C67 H67B 109.7 . . ?
H67A C67 H67B 108.2 . . ?
C71 O71 H71 113.1(16) . . ?
C76 O74 H74 109.8(15) . . ?
O72 C71 O71 124.4(2) . . ?
O72 C71 C72 123.6(2) . . ?
O71 C71 C72 112.1(2) . . ?
O73 C76 O74 122.8(2) . . ?
O73 C76 C75 123.7(3) . . ?
O74 C76 C75 113.6(3) . . ?
C72 C73 C74 111.9(2) . . ?
C72 C73 H73A 109.2 . . ?
C74 C73 H73A 109.2 . . ?
C72 C73 H73B 109.2 . . ?
C74 C73 H73B 109.2 . . ?
H73A C73 H73B 107.9 . . ?
C73 C72 C71 114.8(2) . . ?
C73 C72 H72A 108.6 . . ?
C71 C72 H72A 108.6 . . ?
C73 C72 H72B 108.6 . . ?
C71 C72 H72B 108.6 . . ?
H72A C72 H72B 107.5 . . ?
C73 C74 C75 112.43(19) . . ?
C73 C74 H74A 109.1 . . ?
C75 C74 H74A 109.1 . . ?
C73 C74 H74B 109.1 . . ?
C75 C74 H74B 109.1 . . ?
H74A C74 H74B 107.8 . . ?
C76 C75 C74 110.4(2) . . ?
C76 C75 H75A 109.6 . . ?
C74 C75 H75A 109.6 . . ?
C76 C75 H75B 109.6 . . ?
C74 C75 H75B 109.6 . . ?
H75A C75 H75B 108.1 . . ?
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
Cl11 C22 1.7360(19) . ?
Cl12 C24 1.739(2) . ?
Cl13 C36 1.741(2) . ?
Cl14 C34 1.746(2) . ?
N11 C15 1.348(2) . ?
N11 C13 1.372(2) . ?
N11 C12 1.466(2) . ?
N12 C15 1.319(3) . ?
N12 C14 1.373(3) . ?
O1 C11 1.424(2) . ?
O1 C37 1.429(2) . ?
C11 C21 1.518(3) . ?
C11 C12 1.521(3) . ?
C11 H11 1.0000 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.353(3) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C21 C26 1.389(3) . ?
C21 C22 1.393(3) . ?
C22 C23 1.388(3) . ?
C23 C24 1.374(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.383(3) . ?
C25 C26 1.385(3) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C31 C32 1.389(3) . ?
C31 C36 1.389(3) . ?
C31 C37 1.498(3) . ?
C32 C33 1.389(3) . ?
C32 H32 0.9500 . ?
C33 C34 1.375(3) . ?
C33 H33 0.9500 . ?
C34 C35 1.380(3) . ?
C35 C36 1.385(3) . ?
C35 H35 0.9500 . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
Cl21 C56 1.7391(19) . ?
Cl22 C54 1.740(2) . ?
Cl23 C66 1.7413(19) . ?
Cl24 C64 1.7457(19) . ?
N21 C45 1.352(2) . ?
N21 C43 1.377(2) . ?
N21 C42 1.460(2) . ?
N22 C45 1.319(2) . ?
N22 C44 1.382(3) . ?
O2 C67 1.426(2) . ?
O2 C41 1.426(2) . ?
C41 C51 1.516(3) . ?
C41 C42 1.516(3) . ?
C41 H41 1.0000 . ?
C42 H42A 0.9900 . ?
C42 H42B 0.9900 . ?
C43 C44 1.356(3) . ?
C43 H43 0.9500 . ?
C44 H44 0.9500 . ?
C45 H45 0.9500 . ?
C51 C52 1.389(3) . ?
C51 C56 1.396(3) . ?
C52 C53 1.386(3) . ?
C52 H52 0.9500 . ?
C53 C54 1.383(3) . ?
C53 H53 0.9500 . ?
C54 C55 1.380(3) . ?
C55 C56 1.386(3) . ?
C55 H55 0.9500 . ?
C61 C66 1.385(3) . ?
C61 C62 1.391(3) . ?
C61 C67 1.497(3) . ?
C62 C63 1.386(3) . ?
C62 H62 0.9500 . ?
C63 C64 1.372(3) . ?
C63 H63 0.9500 . ?
C64 C65 1.382(3) . ?
C65 C66 1.385(3) . ?
C65 H65 0.9500 . ?
C67 H67A 0.9900 . ?
C67 H67B 0.9900 . ?
O71 C71 1.314(3) . ?
O71 H71 1.12(3) . ?
O72 C71 1.213(2) . ?
O73 C76 1.215(3) . ?
O74 C76 1.311(3) . ?
O74 H74 1.00(3) . ?
C71 C72 1.513(3) . ?
C76 C75 1.505(3) . ?
C73 C72 1.506(3) . ?
C73 C74 1.525(3) . ?
C73 H73A 0.9900 . ?
C73 H73B 0.9900 . ?
C72 H72A 0.9900 . ?
C72 H72B 0.9900 . ?
C74 C75 1.543(3) . ?
C74 H74A 0.9900 . ?
C74 H74B 0.9900 . ?
C75 H75A 0.9900 . ?
C75 H75B 0.9900 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O71 H71 N12 1.12(3) 1.50(3) 2.616(2) 172(3) .
O74 H74 N22 1.00(3) 1.60(3) 2.590(2) 172(2) .
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
C37 O1 C11 C21 -72.45(19) . . . . ?
C37 O1 C11 C12 168.94(15) . . . . ?
C15 N11 C12 C11 74.7(2) . . . . ?
C13 N11 C12 C11 -105.3(2) . . . . ?
O1 C11 C12 N11 -75.09(19) . . . . ?
C21 C11 C12 N11 163.85(16) . . . . ?
C15 N11 C13 C14 0.1(2) . . . . ?
C12 N11 C13 C14 -179.84(17) . . . . ?
N11 C13 C14 N12 -0.4(2) . . . . ?
C15 N12 C14 C13 0.6(2) . . . . ?
C14 N12 C15 N11 -0.5(2) . . . . ?
C13 N11 C15 N12 0.2(2) . . . . ?
C12 N11 C15 N12 -179.81(17) . . . . ?
O1 C11 C21 C26 -26.0(2) . . . . ?
C12 C11 C21 C26 90.9(2) . . . . ?
O1 C11 C21 C22 157.26(18) . . . . ?
C12 C11 C21 C22 -85.9(2) . . . . ?
C26 C21 C22 C23 -0.6(3) . . . . ?
C11 C21 C22 C23 176.31(18) . . . . ?
C26 C21 C22 Cl11 -179.79(15) . . . . ?
C11 C21 C22 Cl11 -2.9(3) . . . . ?
C21 C22 C23 C24 0.5(3) . . . . ?
Cl11 C22 C23 C24 179.77(16) . . . . ?
C22 C23 C24 C25 0.0(3) . . . . ?
C22 C23 C24 Cl12 179.56(16) . . . . ?
C23 C24 C25 C26 -0.5(3) . . . . ?
Cl12 C24 C25 C26 179.95(16) . . . . ?
C24 C25 C26 C21 0.5(3) . . . . ?
C22 C21 C26 C25 0.0(3) . . . . ?
C11 C21 C26 C25 -176.89(19) . . . . ?
C36 C31 C32 C33 -0.6(3) . . . . ?
C37 C31 C32 C33 178.74(19) . . . . ?
C31 C32 C33 C34 -0.2(3) . . . . ?
C32 C33 C34 C35 1.3(3) . . . . ?
C32 C33 C34 Cl14 -177.31(16) . . . . ?
C33 C34 C35 C36 -1.4(3) . . . . ?
Cl14 C34 C35 C36 177.20(15) . . . . ?
C34 C35 C36 C31 0.5(3) . . . . ?
C34 C35 C36 Cl13 -179.30(15) . . . . ?
C32 C31 C36 C35 0.5(3) . . . . ?
C37 C31 C36 C35 -178.92(18) . . . . ?
C32 C31 C36 Cl13 -179.70(16) . . . . ?
C37 C31 C36 Cl13 0.9(3) . . . . ?
C11 O1 C37 C31 176.57(15) . . . . ?
C32 C31 C37 O1 5.1(3) . . . . ?
C36 C31 C37 O1 -175.54(16) . . . . ?
C67 O2 C41 C51 74.84(19) . . . . ?
C67 O2 C41 C42 -167.54(15) . . . . ?
C45 N21 C42 C41 -81.0(2) . . . . ?
C43 N21 C42 C41 99.9(2) . . . . ?
O2 C41 C42 N21 66.87(19) . . . . ?
C51 C41 C42 N21 -172.93(15) . . . . ?
C45 N21 C43 C44 0.1(2) . . . . ?
C42 N21 C43 C44 179.37(17) . . . . ?
N21 C43 C44 N22 0.0(2) . . . . ?
C45 N22 C44 C43 -0.1(2) . . . . ?
C44 N22 C45 N21 0.2(2) . . . . ?
C43 N21 C45 N22 -0.2(2) . . . . ?
C42 N21 C45 N22 -179.47(16) . . . . ?
O2 C41 C51 C52 21.3(2) . . . . ?
C42 C41 C51 C52 -94.7(2) . . . . ?
O2 C41 C51 C56 -161.79(17) . . . . ?
C42 C41 C51 C56 82.2(2) . . . . ?
C56 C51 C52 C53 -0.2(3) . . . . ?
C41 C51 C52 C53 176.87(18) . . . . ?
C51 C52 C53 C54 -0.8(3) . . . . ?
C52 C53 C54 C55 0.9(3) . . . . ?
C52 C53 C54 Cl22 179.99(15) . . . . ?
C53 C54 C55 C56 0.0(3) . . . . ?
Cl22 C54 C55 C56 -179.08(14) . . . . ?
C54 C55 C56 C51 -1.1(3) . . . . ?
C54 C55 C56 Cl21 179.45(15) . . . . ?
C52 C51 C56 C55 1.2(3) . . . . ?
C41 C51 C56 C55 -175.84(17) . . . . ?
C52 C51 C56 Cl21 -179.35(14) . . . . ?
C41 C51 C56 Cl21 3.6(3) . . . . ?
C66 C61 C62 C63 0.9(3) . . . . ?
C67 C61 C62 C63 -178.48(18) . . . . ?
C61 C62 C63 C64 0.3(3) . . . . ?
C62 C63 C64 C65 -1.8(3) . . . . ?
C62 C63 C64 Cl24 177.55(15) . . . . ?
C63 C64 C65 C66 1.9(3) . . . . ?
Cl24 C64 C65 C66 -177.45(15) . . . . ?
C64 C65 C66 C61 -0.6(3) . . . . ?
C64 C65 C66 Cl23 -179.64(14) . . . . ?
C62 C61 C66 C65 -0.8(3) . . . . ?
C67 C61 C66 C65 178.62(18) . . . . ?
C62 C61 C66 Cl23 178.28(15) . . . . ?
C67 C61 C66 Cl23 -2.3(3) . . . . ?
C41 O2 C67 C61 -178.12(15) . . . . ?
C66 C61 C67 O2 176.45(16) . . . . ?
C62 C61 C67 O2 -4.2(3) . . . . ?
C74 C73 C72 C71 -176.8(2) . . . . ?
O72 C71 C72 C73 -3.8(3) . . . . ?
O71 C71 C72 C73 177.4(2) . . . . ?
C72 C73 C74 C75 -70.8(3) . . . . ?
O73 C76 C75 C74 -93.0(3) . . . . ?
O74 C76 C75 C74 85.9(3) . . . . ?
C73 C74 C75 C76 170.7(2) . . . . ?
