#------------------------------------------------------------------------------
#$Date: 2021-02-05 00:57:25 +0200 (Fri, 05 Feb 2021) $
#$Revision: 261597 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/15/7241520.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_7241520
loop_
_publ_author_name
'Bodart, Laurie'
'Prinzo, Maria'
'Derlet, Amélie'
'Tumanov, Nikolay'
'Wouters, Johan'
_publ_section_title
;
 Taking advantage of solvate formation to modulate drug--drug ratio in
 clofaziminium diclofenac salts
;
_journal_issue                   1
_journal_name_full               CrystEngComm
_journal_page_first              185
_journal_page_last               201
_journal_paper_doi               10.1039/D0CE01400A
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety
;
C27 H23 Cl2 N4 1+, C14 H10 Cl2 N O2 1-, 
C14 H11 Cl2 N O2
;
_chemical_formula_sum            'C55 H44 Cl6 N6 O4'
_chemical_formula_weight         1065.66
_chemical_name_common
;
clofaziminium diclofenac (1-) diclofenac salt cocrystal
;
_chemical_name_systematic
;
 2-{2-[(2,6-dichlorophenyl)amino]phenyl}acetic acid N-
[(2E)-10-(4-chlorophenyl)-3-[(4-
chlorophenyl)amino]-2,10-dihydrophenazin-2-
ylidene]propan-2-aminium 2-{2-[(2,6-
dichlorophenyl)amino]phenyl}acetate
;
_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     dual
_atom_sites_solution_secondary   dual
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2020-09-17 deposited with the CCDC.	2020-11-20 downloaded from the CCDC.
;
_cell_angle_alpha                101.568(2)
_cell_angle_beta                 105.173(2)
_cell_angle_gamma                94.286(2)
_cell_formula_units_Z            2
_cell_length_a                   10.8837(2)
_cell_length_b                   14.4737(3)
_cell_length_c                   17.7519(4)
_cell_measurement_reflns_used    14280
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      66.9040
_cell_measurement_theta_min      3.1130
_cell_volume                     2620.06(10)
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 5.1856
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            26706
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.100
_diffrn_reflns_theta_max         67.100
_diffrn_reflns_theta_min         2.649
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.410
_exptl_absorpt_correction_T_max  0.831
_exptl_absorpt_correction_T_min  0.358
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
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)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'Dark red'
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_description       Plate
_exptl_crystal_F_000             1100
_exptl_crystal_size_max          0.540
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.491
_refine_diff_density_min         -0.498
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     657
_refine_ls_number_reflns         9218
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0504
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0678P)²+0.9591P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1352
_refine_ls_wR_factor_ref         0.1407
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8043
_reflns_number_total             9218
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce01400a2.cif
_cod_data_source_block           lb0765_CFZ-DCF12_LAG_EtOH_EtOH
_cod_depositor_comments
'Adding full bibliography for 7241513--7241524.cif.'
_cod_database_code               7241520
_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   0.260
_shelx_estimated_absorpt_t_max   0.822
_oxdiff_exptl_absorpt_empirical_full_min 0.844
_oxdiff_exptl_absorpt_empirical_full_max 1.147
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
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 0.85591(12) 1.12858(7) 0.06659(5) 0.1272(4) Uani 1 1 d . . . . .
Cl2 Cl 1.05288(7) 0.48793(6) 0.71384(4) 0.0879(2) Uani 1 1 d . . . . .
N1 N 1.03915(15) 0.98740(11) 0.36031(10) 0.0480(4) Uani 1 1 d . . . . .
N2 N 1.15547(16) 0.94182(11) 0.50591(10) 0.0531(4) Uani 1 1 d . . . . .
N3 N 0.84524(17) 0.66821(12) 0.44499(11) 0.0542(4) Uani 1 1 d . . . . .
H3 H 0.764(3) 0.6515(18) 0.4227(15) 0.065 Uiso 1 1 d . U . . .
N4 N 0.74765(16) 0.69751(13) 0.29338(10) 0.0546(4) Uani 1 1 d . . . . .
H4 H 0.729(2) 0.6442(19) 0.3064(15) 0.065 Uiso 1 1 d . U . . .
C1 C 1.2067(2) 1.12333(15) 0.39346(16) 0.0638(5) Uani 1 1 d . . . . .
H1 H 1.170340 1.140441 0.345523 0.077 Uiso 1 1 calc R U . . .
C2 C 1.3163(2) 1.17496(17) 0.44642(19) 0.0781(7) Uani 1 1 d . . . . .
H2 H 1.354472 1.227274 0.433847 0.094 Uiso 1 1 calc R U . . .
C3 C 1.3724(2) 1.15125(18) 0.51878(19) 0.0812(8) Uani 1 1 d . . . . .
H3A H 1.447220 1.187470 0.553826 0.097 Uiso 1 1 calc R U . . .
C4 C 1.3177(2) 1.07503(16) 0.53816(17) 0.0703(6) Uani 1 1 d . . . . .
H4A H 1.354820 1.059688 0.586774 0.084 Uiso 1 1 calc R U . . .
C5 C 1.20506(19) 1.01918(13) 0.48499(13) 0.0535(5) Uani 1 1 d . . . . .
C6 C 1.05343(17) 0.88715(13) 0.45405(11) 0.0464(4) Uani 1 1 d . . . . .
C7 C 1.00253(18) 0.80646(13) 0.47458(12) 0.0495(4) Uani 1 1 d . . . . .
H7 H 1.041591 0.794425 0.524248 0.059 Uiso 1 1 calc R U . . .
C8 C 0.89851(18) 0.74519(13) 0.42489(11) 0.0475(4) Uani 1 1 d . . . . .
C9 C 0.83975(17) 0.76222(13) 0.34502(11) 0.0470(4) Uani 1 1 d . . . . .
C10 C 0.88474(18) 0.84576(14) 0.32595(12) 0.0491(4) Uani 1 1 d . . . . .
H10 H 0.842935 0.859983 0.277661 0.059 Uiso 1 1 calc R U . . .
C11 C 0.98945(17) 0.90690(13) 0.37738(11) 0.0453(4) Uani 1 1 d . . . . .
C12 C 1.14965(18) 1.04416(13) 0.41229(13) 0.0508(4) Uani 1 1 d . . . . .
C13 C 0.98152(19) 1.01444(14) 0.28592(12) 0.0506(4) Uani 1 1 d . . . . .
C14 C 0.9042(3) 1.08543(18) 0.28610(16) 0.0729(6) Uani 1 1 d . . . . .
H14 H 0.879386 1.109811 0.331633 0.087 Uiso 1 1 calc R U . . .
C15 C 0.8640(3) 1.1200(2) 0.21807(19) 0.0873(8) Uani 1 1 d . . . . .
H15 H 0.813122 1.168878 0.217601 0.105 Uiso 1 1 calc R U . . .
C16 C 0.8995(3) 1.08180(18) 0.15117(16) 0.0747(7) Uani 1 1 d . . . . .
C17 C 0.9717(2) 1.00887(18) 0.14968(15) 0.0701(6) Uani 1 1 d . . . . .
H17 H 0.992318 0.982260 0.103083 0.084 Uiso 1 1 calc R U . . .
C18 C 1.0141(2) 0.97484(16) 0.21800(13) 0.0588(5) Uani 1 1 d . . . . .
H18 H 1.064229 0.925543 0.218000 0.071 Uiso 1 1 calc R U . . .
C19 C 0.89968(19) 0.63163(13) 0.51223(12) 0.0502(4) Uani 1 1 d . . . . .
C20 C 0.8178(2) 0.59457(16) 0.55018(14) 0.0608(5) Uani 1 1 d . . . . .
H20 H 0.730413 0.598763 0.533396 0.073 Uiso 1 1 calc R U . . .
C21 C 0.8648(2) 0.55145(18) 0.61267(15) 0.0665(6) Uani 1 1 d . . . . .
H21 H 0.809271 0.526039 0.637462 0.080 Uiso 1 1 calc R U . . .
C22 C 0.9942(2) 0.54645(16) 0.63786(13) 0.0595(5) Uani 1 1 d . . . . .
C23 C 1.0783(2) 0.58471(15) 0.60217(13) 0.0557(5) Uani 1 1 d . . . . .
H23 H 1.166066 0.582690 0.620650 0.067 Uiso 1 1 calc R U . . .
C24 C 1.03013(19) 0.62584(14) 0.53885(12) 0.0527(4) Uani 1 1 d . . . . .
H24 H 1.085791 0.650067 0.513580 0.063 Uiso 1 1 calc R U . . .
C25 C 0.6741(2) 0.70523(16) 0.21321(13) 0.0607(5) Uani 1 1 d . . . . .
H25 H 0.725954 0.748765 0.194210 0.073 Uiso 1 1 calc R U . . .
C26 C 0.6465(5) 0.6092(3) 0.1559(2) 0.1217(14) Uani 1 1 d . . . . .
H26A H 0.725881 0.584740 0.155092 0.183 Uiso 1 1 calc R U . . .
H26B H 0.602534 0.615434 0.103050 0.183 Uiso 1 1 calc R U . . .
H26C H 0.593620 0.566351 0.172901 0.183 Uiso 1 1 calc R U . . .
C27 C 0.5549(4) 0.7448(4) 0.2178(2) 0.156(2) Uani 1 1 d . . . . .
H27A H 0.501199 0.701228 0.233698 0.234 Uiso 1 1 calc R U . . .
H27B H 0.510325 0.754336 0.166182 0.234 Uiso 1 1 calc R U . . .
H27C H 0.575396 0.804532 0.256413 0.234 Uiso 1 1 calc R U . . .
Cl5 Cl 0.28195(7) 0.54170(6) 0.04745(5) 0.0956(2) Uani 1 1 d . . . . .
Cl6 Cl -0.09277(9) 0.75633(7) 0.07954(6) 0.1103(3) Uani 1 1 d . . . . .
O3 O 0.37660(17) 0.67656(12) 0.38683(10) 0.0705(4) Uani 1 1 d . . . . .
H3O H 0.443(3) 0.641(2) 0.385(2) 0.106 Uiso 1 1 d . U . . .
O4 O 0.28234(18) 0.58292(12) 0.26708(10) 0.0749(4) Uani 1 1 d . . . . .
N6 N 0.1461(2) 0.67403(14) 0.14053(12) 0.0673(5) Uani 1 1 d . . . . .
H6 H 0.179(3) 0.631(2) 0.1624(17) 0.081 Uiso 1 1 d . U . . .
C42 C 0.2880(2) 0.65304(15) 0.31846(12) 0.0550(5) Uani 1 1 d . . . . .
C43 C 0.1952(2) 0.72506(17) 0.30861(14) 0.0633(5) Uani 1 1 d . . . . .
H43A H 0.109407 0.692859 0.279532 0.076 Uiso 1 1 calc R U . . .
H43B H 0.192949 0.759981 0.360832 0.076 Uiso 1 1 calc R U . . .
C44 C 0.2376(2) 0.79269(15) 0.26327(13) 0.0573(5) Uani 1 1 d . . . . .
C45 C 0.3072(2) 0.88165(17) 0.30255(16) 0.0715(6) Uani 1 1 d . . . . .
H45 H 0.328835 0.899250 0.358213 0.086 Uiso 1 1 calc R U . . .
C46 C 0.3448(3) 0.94401(18) 0.2616(2) 0.0840(8) Uani 1 1 d . . . . .
H46 H 0.391053 1.003195 0.289113 0.101 Uiso 1 1 calc R U . . .
C47 C 0.3134(3) 0.91815(18) 0.1792(2) 0.0831(8) Uani 1 1 d . . . . .
H47 H 0.337253 0.960529 0.150859 0.100 Uiso 1 1 calc R U . . .
C48 C 0.2469(2) 0.83004(17) 0.13856(16) 0.0699(6) Uani 1 1 d . . . . .
H48 H 0.226240 0.813296 0.082903 0.084 Uiso 1 1 calc R U . . .
C49 C 0.2102(2) 0.76580(15) 0.17972(13) 0.0567(5) Uani 1 1 d . . . . .
C50 C 0.0912(2) 0.64772(16) 0.05715(13) 0.0635(5) Uani 1 1 d . . . . .
C51 C 0.1404(2) 0.58373(18) 0.00685(15) 0.0712(6) Uani 1 1 d . . . . .
C52 C 0.0794(3) 0.5533(2) -0.07442(16) 0.0860(8) Uani 1 1 d . . . . .
H52 H 0.113230 0.509349 -0.106557 0.103 Uiso 1 1 calc R U . . .
C53 C -0.0304(3) 0.5877(2) -0.10726(17) 0.0915(8) Uani 1 1 d . . . . .
H53 H -0.071128 0.567421 -0.161908 0.110 Uiso 1 1 calc R U . . .
C54 C -0.0808(3) 0.6516(2) -0.06052(17) 0.0869(8) Uani 1 1 d . . . . .
H54 H -0.154900 0.675811 -0.083215 0.104 Uiso 1 1 calc R U . . .
C55 C -0.0214(3) 0.68014(18) 0.02072(16) 0.0742(6) Uani 1 1 d . . . . .
Cl3 Cl 0.65738(14) 0.33402(9) 0.10645(9) 0.1552(5) Uani 1 1 d . . . . .
Cl4 Cl 0.25498(8) 0.17376(7) 0.17906(7) 0.1214(3) Uani 1 1 d . . . . .
O1 O 0.64114(17) 0.50220(12) 0.30290(13) 0.0809(5) Uani 1 1 d . . . . .
O2 O 0.57609(15) 0.60066(11) 0.39119(11) 0.0717(4) Uani 1 1 d . . . . .
N5 N 0.4872(2) 0.31331(15) 0.21087(13) 0.0719(5) Uani 1 1 d . . . . .
H5 H 0.527(3) 0.367(2) 0.2116(17) 0.086 Uiso 1 1 d . U . . .
C28 C 0.5733(2) 0.51867(16) 0.34827(15) 0.0621(5) Uani 1 1 d . . . . .
C29 C 0.4825(2) 0.43794(16) 0.35544(17) 0.0675(6) Uani 1 1 d . . . . .
H29A H 0.459073 0.457000 0.404839 0.081 Uiso 1 1 calc R U . . .
H29B H 0.404611 0.427657 0.311332 0.081 Uiso 1 1 calc R U . . .
C30 C 0.5374(2) 0.34538(15) 0.35496(14) 0.0591(5) Uani 1 1 d . . . . .
C31 C 0.5906(2) 0.31930(18) 0.42616(15) 0.0688(6) Uani 1 1 d . . . . .
H31 H 0.595979 0.361133 0.474443 0.083 Uiso 1 1 calc R U . . .
C32 C 0.6359(2) 0.2328(2) 0.42744(17) 0.0746(7) Uani 1 1 d . . . . .
H32 H 0.672511 0.217039 0.475941 0.089 Uiso 1 1 calc R U . . .
C33 C 0.6263(2) 0.17063(19) 0.35634(18) 0.0752(7) Uani 1 1 d . . . . .
H33 H 0.653476 0.111249 0.356558 0.090 Uiso 1 1 calc R U . . .
C34 C 0.5765(2) 0.19540(17) 0.28428(16) 0.0712(6) Uani 1 1 d . . . . .
H34 H 0.571432 0.152990 0.236334 0.085 Uiso 1 1 calc R U . . .
C35 C 0.5341(2) 0.28322(15) 0.28314(14) 0.0602(5) Uani 1 1 d . . . . .
C36 C 0.4554(3) 0.24835(18) 0.13707(16) 0.0749(7) Uani 1 1 d . . . . .
C37 C 0.3490(3) 0.1780(2) 0.1150(2) 0.0919(9) Uani 1 1 d . . . . .
C38 C 0.3153(5) 0.1127(3) 0.0436(3) 0.1322(16) Uani 1 1 d . . . . .
H38 H 0.245865 0.065394 0.031742 0.159 Uiso 1 1 calc R U . . .
C39 C 0.3824(7) 0.1167(4) -0.0094(3) 0.150(2) Uani 1 1 d . . . . .
H39 H 0.357844 0.072516 -0.058309 0.180 Uiso 1 1 calc R U . . .
C40 C 0.4875(6) 0.1853(4) 0.0074(3) 0.1354(15) Uani 1 1 d . . . . .
H40 H 0.533162 0.187944 -0.029856 0.163 Uiso 1 1 calc R U . . .
C41 C 0.5234(4) 0.2505(2) 0.0816(2) 0.0995(9) Uani 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_
_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
C11 N1 C12 121.24(16) . . ?
C11 N1 C13 121.10(16) . . ?
C12 N1 C13 117.61(15) . . ?
C6 N2 C5 118.05(17) . . ?
C8 N3 C19 125.80(17) . . ?
C8 N3 H3 115.6(16) . . ?
C19 N3 H3 116.2(16) . . ?
C9 N4 C25 125.91(17) . . ?
C9 N4 H4 118.8(16) . . ?
C25 N4 H4 115.3(16) . . ?
C2 C1 C12 119.1(2) . . ?
C2 C1 H1 120.4 . . ?
C12 C1 H1 120.4 . . ?
C1 C2 C3 121.6(2) . . ?
C1 C2 H2 119.2 . . ?
C3 C2 H2 119.2 . . ?
C4 C3 C2 119.9(2) . . ?
C4 C3 H3A 120.0 . . ?
C2 C3 H3A 120.0 . . ?
C3 C4 C5 120.4(2) . . ?
C3 C4 H4A 119.8 . . ?
C5 C4 H4A 119.8 . . ?
N2 C5 C12 122.66(18) . . ?
N2 C5 C4 118.4(2) . . ?
C12 C5 C4 118.94(19) . . ?
N2 C6 C7 118.51(17) . . ?
N2 C6 C11 123.36(17) . . ?
C7 C6 C11 118.12(16) . . ?
C8 C7 C6 122.93(18) . . ?
C8 C7 H7 118.5 . . ?
C6 C7 H7 118.5 . . ?
C7 C8 N3 123.66(18) . . ?
C7 C8 C9 118.50(16) . . ?
N3 C8 C9 117.84(17) . . ?
N4 C9 C10 122.47(18) . . ?
N4 C9 C8 118.69(16) . . ?
C10 C9 C8 118.83(16) . . ?
C11 C10 C9 121.30(17) . . ?
C11 C10 H10 119.3 . . ?
C9 C10 H10 119.3 . . ?
N1 C11 C10 123.38(17) . . ?
N1 C11 C6 116.62(16) . . ?
C10 C11 C6 120.00(16) . . ?
N1 C12 C1 122.06(19) . . ?
N1 C12 C5 117.96(17) . . ?
C1 C12 C5 119.97(19) . . ?
C18 C13 C14 120.9(2) . . ?
C18 C13 N1 119.36(18) . . ?
C14 C13 N1 119.43(19) . . ?
C13 C14 C15 119.3(2) . . ?
C13 C14 H14 120.4 . . ?
C15 C14 H14 120.4 . . ?
C16 C15 C14 119.4(2) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C17 C16 C15 121.5(2) . . ?
C17 C16 Cl1 118.6(2) . . ?
C15 C16 Cl1 119.9(2) . . ?
C16 C17 C18 119.4(2) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 H17 120.3 . . ?
C13 C18 C17 119.4(2) . . ?
C13 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?
C20 C19 C24 118.82(18) . . ?
C20 C19 N3 118.16(18) . . ?
C24 C19 N3 122.89(17) . . ?
C21 C20 C19 120.67(19) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C22 C21 C20 119.44(19) . . ?
C22 C21 H21 120.3 . . ?
C20 C21 H21 120.3 . . ?
C21 C22 C23 121.04(19) . . ?
C21 C22 Cl2 119.57(16) . . ?
C23 C22 Cl2 119.36(17) . . ?
C24 C23 C22 119.03(19) . . ?
C24 C23 H23 120.5 . . ?
C22 C23 H23 120.5 . . ?
C23 C24 C19 120.96(18) . . ?
C23 C24 H24 119.5 . . ?
C19 C24 H24 119.5 . . ?
N4 C25 C27 109.6(2) . . ?
N4 C25 C26 109.9(2) . . ?
C27 C25 C26 111.4(3) . . ?
N4 C25 H25 108.6 . . ?
C27 C25 H25 108.6 . . ?
C26 C25 H25 108.6 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C42 O3 H3O 110(2) . . ?
C50 N6 C49 122.09(19) . . ?
C50 N6 H6 116(2) . . ?
C49 N6 H6 113(2) . . ?
O4 C42 O3 124.0(2) . . ?
O4 C42 C43 123.2(2) . . ?
O3 C42 C43 112.73(19) . . ?
C44 C43 C42 109.10(18) . . ?
C44 C43 H43A 109.9 . . ?
C42 C43 H43A 109.9 . . ?
C44 C43 H43B 109.9 . . ?
C42 C43 H43B 109.9 . . ?
H43A C43 H43B 108.3 . . ?
C45 C44 C49 118.4(2) . . ?
C45 C44 C43 121.6(2) . . ?
C49 C44 C43 120.1(2) . . ?
C46 C45 C44 121.9(3) . . ?
C46 C45 H45 119.1 . . ?
C44 C45 H45 119.1 . . ?
C45 C46 C47 119.3(2) . . ?
C45 C46 H46 120.4 . . ?
C47 C46 H46 120.4 . . ?
C48 C47 C46 120.4(3) . . ?
C48 C47 H47 119.8 . . ?
C46 C47 H47 119.8 . . ?
C47 C48 C49 120.7(3) . . ?
C47 C48 H48 119.6 . . ?
C49 C48 H48 119.6 . . ?
C48 C49 C44 119.3(2) . . ?
C48 C49 N6 122.3(2) . . ?
C44 C49 N6 118.33(19) . . ?
C55 C50 C51 116.0(2) . . ?
C55 C50 N6 121.2(2) . . ?
C51 C50 N6 122.6(2) . . ?
C52 C51 C50 121.7(3) . . ?
C52 C51 Cl5 119.5(2) . . ?
C50 C51 Cl5 118.80(19) . . ?
C53 C52 C51 119.9(3) . . ?
C53 C52 H52 120.0 . . ?
C51 C52 H52 120.0 . . ?
C54 C53 C52 120.3(3) . . ?
C54 C53 H53 119.8 . . ?
C52 C53 H53 119.8 . . ?
C53 C54 C55 119.6(3) . . ?
C53 C54 H54 120.2 . . ?
C55 C54 H54 120.2 . . ?
C54 C55 C50 122.3(3) . . ?
C54 C55 Cl6 118.5(2) . . ?
C50 C55 Cl6 119.1(2) . . ?
C36 N5 C35 120.6(2) . . ?
C36 N5 H5 114(2) . . ?
C35 N5 H5 113(2) . . ?
O1 C28 O2 123.1(2) . . ?
O1 C28 C29 119.6(2) . . ?
O2 C28 C29 117.3(2) . . ?
C30 C29 C28 114.16(18) . . ?
C30 C29 H29A 108.7 . . ?
C28 C29 H29A 108.7 . . ?
C30 C29 H29B 108.7 . . ?
C28 C29 H29B 108.7 . . ?
H29A C29 H29B 107.6 . . ?
C31 C30 C35 118.4(2) . . ?
C31 C30 C29 120.5(2) . . ?
C35 C30 C29 121.1(2) . . ?
C32 C31 C30 121.8(2) . . ?
C32 C31 H31 119.1 . . ?
C30 C31 H31 119.1 . . ?
C33 C32 C31 119.1(2) . . ?
C33 C32 H32 120.4 . . ?
C31 C32 H32 120.4 . . ?
C32 C33 C34 120.5(2) . . ?
C32 C33 H33 119.7 . . ?
C34 C33 H33 119.7 . . ?
C33 C34 C35 120.3(3) . . ?
C33 C34 H34 119.9 . . ?
C35 C34 H34 119.9 . . ?
C34 C35 C30 119.8(2) . . ?
C34 C35 N5 122.3(2) . . ?
C30 C35 N5 117.9(2) . . ?
C41 C36 N5 122.9(3) . . ?
C41 C36 C37 116.6(3) . . ?
N5 C36 C37 120.5(3) . . ?
C38 C37 C36 122.3(4) . . ?
C38 C37 Cl4 118.2(3) . . ?
C36 C37 Cl4 119.4(3) . . ?
C39 C38 C37 119.9(4) . . ?
C39 C38 H38 120.1 . . ?
C37 C38 H38 120.1 . . ?
C38 C39 C40 121.2(4) . . ?
C38 C39 H39 119.4 . . ?
C40 C39 H39 119.4 . . ?
C39 C40 C41 118.4(5) . . ?
C39 C40 H40 120.8 . . ?
C41 C40 H40 120.8 . . ?
C36 C41 C40 121.5(4) . . ?
C36 C41 Cl3 118.6(3) . . ?
C40 C41 Cl3 119.9(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
Cl1 C16 1.738(2) . ?
Cl2 C22 1.741(2) . ?
N1 C11 1.369(2) . ?
N1 C12 1.393(3) . ?
N1 C13 1.449(2) . ?
N2 C6 1.322(2) . ?
N2 C5 1.365(3) . ?
N3 C8 1.370(2) . ?
N3 C19 1.409(3) . ?
N3 H3 0.87(3) . ?
N4 C9 1.325(3) . ?
N4 C25 1.469(3) . ?
N4 H4 0.87(3) . ?
C1 C2 1.365(4) . ?
C1 C12 1.402(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.392(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.361(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.410(3) . ?
C4 H4A 0.9300 . ?
C5 C12 1.404(3) . ?
C6 C7 1.408(3) . ?
C6 C11 1.452(3) . ?
C7 C8 1.364(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.473(3) . ?
C9 C10 1.407(3) . ?
C10 C11 1.377(3) . ?
C10 H10 0.9300 . ?
C13 C18 1.373(3) . ?
C13 C14 1.376(3) . ?
C14 C15 1.378(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.369(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.362(4) . ?
C17 C18 1.381(3) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.387(3) . ?
C19 C24 1.389(3) . ?
C20 C21 1.382(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.374(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.384(3) . ?
C23 C24 1.378(3) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 C27 1.472(4) . ?
C25 C26 1.506(4) . ?
C25 H25 0.9800 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
Cl5 C51 1.731(3) . ?
Cl6 C55 1.732(3) . ?
O3 C42 1.301(3) . ?
O3 H3O 0.91(4) . ?
O4 C42 1.207(3) . ?
N6 C50 1.404(3) . ?
N6 C49 1.404(3) . ?
N6 H6 0.85(3) . ?
C42 C43 1.508(3) . ?
C43 C44 1.504(3) . ?
C43 H43A 0.9700 . ?
C43 H43B 0.9700 . ?
C44 C45 1.391(3) . ?
C44 C49 1.400(3) . ?
C45 C46 1.369(4) . ?
C45 H45 0.9300 . ?
C46 C47 1.377(4) . ?
C46 H46 0.9300 . ?
C47 C48 1.375(4) . ?
C47 H47 0.9300 . ?
C48 C49 1.388(3) . ?
C48 H48 0.9300 . ?
C50 C55 1.390(4) . ?
C50 C51 1.391(4) . ?
C51 C52 1.384(4) . ?
C52 C53 1.363(5) . ?
C52 H52 0.9300 . ?
C53 C54 1.360(4) . ?
C53 H53 0.9300 . ?
C54 C55 1.379(4) . ?
C54 H54 0.9300 . ?
Cl3 C41 1.723(4) . ?
Cl4 C37 1.724(4) . ?
O1 C28 1.229(3) . ?
O2 C28 1.269(3) . ?
N5 C36 1.393(4) . ?
N5 C35 1.418(3) . ?
N5 H5 0.86(3) . ?
C28 C29 1.520(3) . ?
C29 C30 1.507(3) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 C31 1.384(3) . ?
C30 C35 1.395(3) . ?
C31 C32 1.382(4) . ?
C31 H31 0.9300 . ?
C32 C33 1.369(4) . ?
C32 H32 0.9300 . ?
C33 C34 1.381(4) . ?
C33 H33 0.9300 . ?
C34 C35 1.387(3) . ?
C34 H34 0.9300 . ?
C36 C41 1.382(4) . ?
C36 C37 1.399(4) . ?
C37 C38 1.363(6) . ?
C38 C39 1.340(8) . ?
C38 H38 0.9300 . ?
C39 C40 1.385(7) . ?
C39 H39 0.9300 . ?
C40 C41 1.398(6) . ?
C40 H40 0.9300 . ?
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
N3 H3 O2 0.87(3) 2.01(3) 2.860(2) 168(2) .
N4 H4 O1 0.87(3) 2.18(3) 3.028(2) 163(2) .
N5 H5 O1 0.86(3) 2.30(3) 3.007(3) 139(3) .
N6 H6 O4 0.85(3) 2.18(3) 2.953(3) 151(3) .
O3 H3O O2 0.91(4) 1.59(4) 2.496(2) 168(3) .
C3 H3A O3 0.93 2.49 3.376(3) 159.0 2_776
C31 H31 O3 0.93 2.57 3.232(3) 128.0 2_666
C26 H26C O1 0.96 2.60 3.302(5) 130.2 .
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
C12 C1 C2 C3 -0.3(4) . . . . ?
C1 C2 C3 C4 -0.1(4) . . . . ?
C2 C3 C4 C5 0.7(4) . . . . ?
C6 N2 C5 C12 2.1(3) . . . . ?
C6 N2 C5 C4 -176.78(19) . . . . ?
C3 C4 C5 N2 178.2(2) . . . . ?
C3 C4 C5 C12 -0.7(4) . . . . ?
C5 N2 C6 C7 179.17(18) . . . . ?
C5 N2 C6 C11 -2.0(3) . . . . ?
N2 C6 C7 C8 -179.28(18) . . . . ?
C11 C6 C7 C8 1.8(3) . . . . ?
C6 C7 C8 N3 -177.76(19) . . . . ?
C6 C7 C8 C9 2.3(3) . . . . ?
C19 N3 C8 C7 -11.0(3) . . . . ?
C19 N3 C8 C9 168.91(18) . . . . ?
C25 N4 C9 C10 -4.5(3) . . . . ?
C25 N4 C9 C8 176.51(19) . . . . ?
C7 C8 C9 N4 172.85(18) . . . . ?
N3 C8 C9 N4 -7.1(3) . . . . ?
C7 C8 C9 C10 -6.2(3) . . . . ?
N3 C8 C9 C10 173.89(18) . . . . ?
N4 C9 C10 C11 -173.04(18) . . . . ?
C8 C9 C10 C11 6.0(3) . . . . ?
C12 N1 C11 C10 -176.31(18) . . . . ?
C13 N1 C11 C10 1.2(3) . . . . ?
C12 N1 C11 C6 3.4(3) . . . . ?
C13 N1 C11 C6 -179.14(16) . . . . ?
C9 C10 C11 N1 177.86(17) . . . . ?
C9 C10 C11 C6 -1.8(3) . . . . ?
N2 C6 C11 N1 -0.7(3) . . . . ?
C7 C6 C11 N1 178.14(17) . . . . ?
N2 C6 C11 C10 178.99(18) . . . . ?
C7 C6 C11 C10 -2.2(3) . . . . ?
C11 N1 C12 C1 175.77(19) . . . . ?
C13 N1 C12 C1 -1.8(3) . . . . ?
C11 N1 C12 C5 -3.3(3) . . . . ?
C13 N1 C12 C5 179.14(17) . . . . ?
C2 C1 C12 N1 -178.8(2) . . . . ?
C2 C1 C12 C5 0.3(3) . . . . ?
N2 C5 C12 N1 0.5(3) . . . . ?
C4 C5 C12 N1 179.35(19) . . . . ?
N2 C5 C12 C1 -178.63(19) . . . . ?
C4 C5 C12 C1 0.3(3) . . . . ?
C11 N1 C13 C18 -83.9(2) . . . . ?
C12 N1 C13 C18 93.7(2) . . . . ?
C11 N1 C13 C14 101.9(2) . . . . ?
C12 N1 C13 C14 -80.6(2) . . . . ?
C18 C13 C14 C15 -3.0(4) . . . . ?
N1 C13 C14 C15 171.2(2) . . . . ?
C13 C14 C15 C16 1.3(4) . . . . ?
C14 C15 C16 C17 1.4(4) . . . . ?
C14 C15 C16 Cl1 -176.9(2) . . . . ?
C15 C16 C17 C18 -2.4(4) . . . . ?
Cl1 C16 C17 C18 175.94(19) . . . . ?
C14 C13 C18 C17 2.0(3) . . . . ?
N1 C13 C18 C17 -172.15(19) . . . . ?
C16 C17 C18 C13 0.7(4) . . . . ?
C8 N3 C19 C20 144.6(2) . . . . ?
C8 N3 C19 C24 -39.5(3) . . . . ?
C24 C19 C20 C21 -0.9(3) . . . . ?
N3 C19 C20 C21 175.2(2) . . . . ?
C19 C20 C21 C22 0.8(4) . . . . ?
C20 C21 C22 C23 0.6(4) . . . . ?
C20 C21 C22 Cl2 -177.4(2) . . . . ?
C21 C22 C23 C24 -1.9(3) . . . . ?
Cl2 C22 C23 C24 176.11(17) . . . . ?
C22 C23 C24 C19 1.8(3) . . . . ?
C20 C19 C24 C23 -0.5(3) . . . . ?
N3 C19 C24 C23 -176.4(2) . . . . ?
C9 N4 C25 C27 -93.4(4) . . . . ?
C9 N4 C25 C26 143.8(3) . . . . ?
O4 C42 C43 C44 -82.4(3) . . . . ?
O3 C42 C43 C44 95.4(2) . . . . ?
C42 C43 C44 C45 -98.6(2) . . . . ?
C42 C43 C44 C49 79.8(3) . . . . ?
C49 C44 C45 C46 2.5(3) . . . . ?
C43 C44 C45 C46 -179.2(2) . . . . ?
C44 C45 C46 C47 -0.2(4) . . . . ?
C45 C46 C47 C48 -1.1(4) . . . . ?
C46 C47 C48 C49 0.1(4) . . . . ?
C47 C48 C49 C44 2.2(4) . . . . ?
C47 C48 C49 N6 -177.8(2) . . . . ?
C45 C44 C49 C48 -3.4(3) . . . . ?
C43 C44 C49 C48 178.2(2) . . . . ?
C45 C44 C49 N6 176.6(2) . . . . ?
C43 C44 C49 N6 -1.8(3) . . . . ?
C50 N6 C49 C48 -13.6(4) . . . . ?
C50 N6 C49 C44 166.4(2) . . . . ?
C49 N6 C50 C55 -73.5(3) . . . . ?
C49 N6 C50 C51 110.6(3) . . . . ?
C55 C50 C51 C52 -1.0(4) . . . . ?
N6 C50 C51 C52 175.1(2) . . . . ?
C55 C50 C51 Cl5 178.87(19) . . . . ?
N6 C50 C51 Cl5 -5.0(3) . . . . ?
C50 C51 C52 C53 1.4(4) . . . . ?
Cl5 C51 C52 C53 -178.4(2) . . . . ?
C51 C52 C53 C54 -0.3(5) . . . . ?
C52 C53 C54 C55 -1.1(5) . . . . ?
C53 C54 C55 C50 1.6(4) . . . . ?
C53 C54 C55 Cl6 -176.4(2) . . . . ?
C51 C50 C55 C54 -0.5(4) . . . . ?
N6 C50 C55 C54 -176.7(2) . . . . ?
C51 C50 C55 Cl6 177.47(19) . . . . ?
N6 C50 C55 Cl6 1.3(3) . . . . ?
O1 C28 C29 C30 39.3(3) . . . . ?
O2 C28 C29 C30 -139.7(2) . . . . ?
C28 C29 C30 C31 98.0(3) . . . . ?
C28 C29 C30 C35 -83.1(3) . . . . ?
C35 C30 C31 C32 -2.2(3) . . . . ?
C29 C30 C31 C32 176.8(2) . . . . ?
C30 C31 C32 C33 -1.0(4) . . . . ?
C31 C32 C33 C34 2.5(4) . . . . ?
C32 C33 C34 C35 -0.9(4) . . . . ?
C33 C34 C35 C30 -2.3(4) . . . . ?
C33 C34 C35 N5 177.4(2) . . . . ?
C31 C30 C35 C34 3.8(3) . . . . ?
C29 C30 C35 C34 -175.1(2) . . . . ?
C31 C30 C35 N5 -175.9(2) . . . . ?
C29 C30 C35 N5 5.1(3) . . . . ?
C36 N5 C35 C34 14.2(4) . . . . ?
C36 N5 C35 C30 -166.1(2) . . . . ?
C35 N5 C36 C41 -112.7(3) . . . . ?
C35 N5 C36 C37 68.8(3) . . . . ?
C41 C36 C37 C38 2.0(5) . . . . ?
N5 C36 C37 C38 -179.4(3) . . . . ?
C41 C36 C37 Cl4 -177.2(2) . . . . ?
N5 C36 C37 Cl4 1.4(4) . . . . ?
C36 C37 C38 C39 -2.4(6) . . . . ?
Cl4 C37 C38 C39 176.8(4) . . . . ?
C37 C38 C39 C40 1.1(8) . . . . ?
C38 C39 C40 C41 0.5(8) . . . . ?
N5 C36 C41 C40 -178.8(3) . . . . ?
C37 C36 C41 C40 -0.2(5) . . . . ?
N5 C36 C41 Cl3 2.8(4) . . . . ?
C37 C36 C41 Cl3 -178.6(2) . . . . ?
C39 C40 C41 C36 -1.0(7) . . . . ?
C39 C40 C41 Cl3 177.4(4) . . . . ?
