#------------------------------------------------------------------------------
#$Date: 2021-02-05 00:57:25 +0200 (Fri, 05 Feb 2021) $
#$Revision: 261597 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/15/7241519.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_7241519
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, C14 H10 Cl2 N O2, C2 H3 N, 2(H2 O)
;
_chemical_formula_sum            'C43 H40 Cl4 N6 O4'
_chemical_formula_weight         846.61
_chemical_name_systematic
;
N-[(2E)-10-(4-chlorophenyl)-3-[(4-chlorophenyl)amino]-2,10-
dihydrophenazin-2-ylidene] propan-2-aminium acetonitrile 
2-{2-[(2,6-dichlorophenyl)amino]phenyl}acetate 
dihydrate
;
_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                103.558(2)
_cell_angle_beta                 90.461(2)
_cell_angle_gamma                105.250(2)
_cell_formula_units_Z            2
_cell_length_a                   11.6515(3)
_cell_length_b                   11.7149(3)
_cell_length_c                   16.0793(4)
_cell_measurement_reflns_used    13996
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.9670
_cell_measurement_theta_min      2.8140
_cell_volume                     2052.78(9)
_computing_cell_refinement       'CrysAlisPro 1.171.40.16b (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.16b (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.16b (Rigaku OD, 2018)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 5.1856
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_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  0.0194
_diffrn_reflns_av_unetI/netI     0.0197
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            18621
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.065
_diffrn_reflns_theta_max         67.065
_diffrn_reflns_theta_min         2.835
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.031
_exptl_absorpt_correction_T_max  0.628
_exptl_absorpt_correction_T_min  0.360
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.16b (Rigaku Oxford Diffraction, 2018)
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            'Metallic dark red'
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_description       Plate
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.650
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.515
_refine_diff_density_min         -0.411
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     538
_refine_ls_number_reflns         7196
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0320
_refine_ls_R_factor_gt           0.0312
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0403P)²+0.8440P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0795
_refine_ls_wR_factor_ref         0.0802
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6969
_reflns_number_total             7196
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce01400a2.cif
_cod_data_source_block           lb0517_CFZ-DCF_in_MeCN
_cod_depositor_comments
'Adding full bibliography for 7241513--7241524.cif.'
_cod_database_code               7241519
_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   0.243
_shelx_estimated_absorpt_t_max   0.582
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
Cl2 Cl 0.41051(3) 1.35131(3) 0.99341(2) 0.03300(10) Uani 1 1 d . . . . .
Cl3 Cl 0.31071(3) 0.68581(3) 0.61457(2) 0.03027(9) Uani 1 1 d . . . . .
Cl4 Cl 0.57538(3) 0.89550(4) 0.38710(2) 0.03618(10) Uani 1 1 d . . . . .
Cl1 Cl 0.17444(3) -0.07876(3) 0.65457(3) 0.04606(13) Uani 1 1 d . . . . .
O1 O 0.57877(9) 0.84278(9) 0.73017(6) 0.0262(2) Uani 1 1 d . . . . .
O2 O 0.72141(9) 0.97854(10) 0.82172(7) 0.0336(2) Uani 1 1 d . . . . .
O4 O 0.94722(11) 0.81989(11) 0.98544(8) 0.0378(3) Uani 1 1 d . . . . .
H4OA H 0.979(2) 0.765(2) 0.9608(15) 0.057 Uiso 1 1 d . U . . .
H4OB H 0.939(2) 0.863(2) 0.9458(15) 0.057 Uiso 1 1 d . U . . .
N4 N 0.46228(10) 0.62416(11) 0.77273(7) 0.0203(2) Uani 1 1 d . . . . .
H4 H 0.5036(15) 0.6920(17) 0.7685(11) 0.024 Uiso 1 1 d . U . . .
N2 N 0.02868(10) 0.60627(10) 0.90896(7) 0.0200(2) Uani 1 1 d . . . . .
O3 O 0.93825(12) 0.97254(12) 0.88415(9) 0.0424(3) Uani 1 1 d . . . . .
H3OB H 0.963(2) 1.042(2) 0.9193(17) 0.064 Uiso 1 1 d . U . . .
H3OA H 0.868(2) 0.976(2) 0.8663(16) 0.064 Uiso 1 1 d . U . . .
N1 N 0.08235(10) 0.38897(10) 0.83175(7) 0.0200(2) Uani 1 1 d . . . . .
N3 N 0.40707(10) 0.83772(10) 0.84692(7) 0.0208(2) Uani 1 1 d . . . . .
H3 H 0.4623(16) 0.8356(15) 0.8131(11) 0.025 Uiso 1 1 d . U . . .
N5 N 0.53623(10) 0.82386(11) 0.55555(8) 0.0250(3) Uani 1 1 d . . . . .
H5 H 0.5213(16) 0.8298(16) 0.6064(13) 0.030 Uiso 1 1 d . U . . .
C5 C -0.05303(11) 0.49646(12) 0.90256(8) 0.0199(3) Uani 1 1 d . . . . .
C19 C 0.39893(11) 0.95690(12) 0.88351(8) 0.0195(3) Uani 1 1 d . . . . .
C8 C 0.32604(12) 0.73070(12) 0.84757(8) 0.0194(3) Uani 1 1 d . . . . .
C12 C -0.02912(11) 0.38449(12) 0.86344(8) 0.0201(3) Uani 1 1 d . . . . .
C20 C 0.44063(11) 1.04369(12) 0.83667(9) 0.0213(3) Uani 1 1 d . . . . .
H20 H 0.466382 1.019466 0.780980 0.026 Uiso 1 1 calc R U . . .
C25 C 0.50476(12) 0.51899(12) 0.72917(9) 0.0219(3) Uani 1 1 d . . . . .
H25 H 0.434618 0.451777 0.698918 0.026 Uiso 1 1 calc R U . . .
C11 C 0.16642(11) 0.49685(12) 0.83804(8) 0.0193(3) Uani 1 1 d . . . . .
C30 C 0.74490(12) 0.85682(12) 0.59778(9) 0.0224(3) Uani 1 1 d . . . . .
C6 C 0.13392(11) 0.60817(12) 0.87814(8) 0.0191(3) Uani 1 1 d . . . . .
C9 C 0.35823(11) 0.61649(12) 0.80771(8) 0.0191(3) Uani 1 1 d . . . . .
C28 C 0.67743(12) 0.92529(12) 0.74794(9) 0.0225(3) Uani 1 1 d . . . . .
C1 C -0.11686(12) 0.27372(12) 0.85712(9) 0.0220(3) Uani 1 1 d . . . . .
H1 H -0.101362 0.198392 0.830495 0.026 Uiso 1 1 calc R U . . .
C10 C 0.27751(12) 0.50369(12) 0.80677(8) 0.0208(3) Uani 1 1 d . . . . .
H10 H 0.299628 0.430628 0.784207 0.025 Uiso 1 1 calc R U . . .
C7 C 0.21731(12) 0.72156(12) 0.88141(8) 0.0203(3) Uani 1 1 d . . . . .
H7 H 0.197186 0.794380 0.908141 0.024 Uiso 1 1 calc R U . . .
C2 C -0.22546(12) 0.27538(13) 0.88987(9) 0.0234(3) Uani 1 1 d . . . . .
H2 H -0.284671 0.200548 0.885703 0.028 Uiso 1 1 calc R U . . .
C4 C -0.16548(12) 0.49451(13) 0.93532(9) 0.0224(3) Uani 1 1 d . . . . .
H4A H -0.182580 0.569097 0.961725 0.027 Uiso 1 1 calc R U . . .
C24 C 0.36058(12) 0.99290(12) 0.96515(9) 0.0221(3) Uani 1 1 d . . . . .
H24 H 0.332858 0.934353 0.997663 0.027 Uiso 1 1 calc R U . . .
C22 C 0.40543(12) 1.19825(12) 0.95144(9) 0.0233(3) Uani 1 1 d . . . . .
C21 C 0.44482(12) 1.16470(13) 0.87056(9) 0.0239(3) Uani 1 1 d . . . . .
H21 H 0.474254 1.223992 0.838907 0.029 Uiso 1 1 calc R U . . .
C3 C -0.25019(12) 0.38602(13) 0.92938(9) 0.0238(3) Uani 1 1 d . . . . .
H3A H -0.325405 0.385552 0.951888 0.029 Uiso 1 1 calc R U . . .
C31 C 0.85018(13) 0.82274(14) 0.58446(9) 0.0273(3) Uani 1 1 d . . . . .
H31 H 0.919315 0.868126 0.621347 0.033 Uiso 1 1 calc R U . . .
C35 C 0.64397(12) 0.79063(12) 0.54153(9) 0.0220(3) Uani 1 1 d . . . . .
C13 C 0.10716(11) 0.27528(12) 0.78745(9) 0.0221(3) Uani 1 1 d . . . . .
C36 C 0.43823(12) 0.78217(13) 0.49554(9) 0.0246(3) Uani 1 1 d . . . . .
C41 C 0.32556(13) 0.71852(13) 0.51451(9) 0.0259(3) Uani 1 1 d . . . . .
C34 C 0.65145(13) 0.69208(13) 0.47576(9) 0.0269(3) Uani 1 1 d . . . . .
H34 H 0.583151 0.647048 0.437929 0.032 Uiso 1 1 calc R U . . .
C23 C 0.36284(12) 1.11392(13) 0.99891(9) 0.0234(3) Uani 1 1 d . . . . .
H23 H 0.335426 1.138454 1.053988 0.028 Uiso 1 1 calc R U . . .
C38 C 0.34443(14) 0.76990(14) 0.35608(10) 0.0312(3) Uani 1 1 d . . . . .
H38 H 0.351556 0.787549 0.301323 0.037 Uiso 1 1 calc R U . . .
C14 C 0.14360(12) 0.20620(13) 0.83561(10) 0.0274(3) Uani 1 1 d . . . . .
H14 H 0.155047 0.233692 0.896329 0.033 Uiso 1 1 calc R U . . .
N6 N 0.02764(15) 0.51328(16) 0.66843(11) 0.0510(4) Uani 1 1 d . . . . .
C40 C 0.22556(13) 0.68095(14) 0.45733(11) 0.0317(3) Uani 1 1 d . . . . .
H40 H 0.150889 0.638239 0.472830 0.038 Uiso 1 1 calc R U . . .
C27 C 0.58904(13) 0.55714(13) 0.66294(10) 0.0285(3) Uani 1 1 d . . . . .
H27A H 0.546001 0.580590 0.619972 0.043 Uiso 1 1 calc R U . . .
H27B H 0.619947 0.488762 0.634805 0.043 Uiso 1 1 calc R U . . .
H27C H 0.655564 0.626668 0.691329 0.043 Uiso 1 1 calc R U . . .
C32 C 0.85746(14) 0.72457(15) 0.51903(10) 0.0318(3) Uani 1 1 d . . . . .
H32 H 0.930357 0.702757 0.511575 0.038 Uiso 1 1 calc R U . . .
C33 C 0.75717(14) 0.65868(14) 0.46466(10) 0.0309(3) Uani 1 1 d . . . . .
H33 H 0.760725 0.590774 0.419868 0.037 Uiso 1 1 calc R U . . .
C29 C 0.74067(13) 0.96229(13) 0.67123(9) 0.0255(3) Uani 1 1 d . . . . .
H29A H 0.699580 1.014941 0.649845 0.031 Uiso 1 1 calc R U . . .
H29B H 0.823382 1.011495 0.691185 0.031 Uiso 1 1 calc R U . . .
C18 C 0.09165(13) 0.23936(13) 0.69903(10) 0.0278(3) Uani 1 1 d . . . . .
H18 H 0.066495 0.288586 0.667331 0.033 Uiso 1 1 calc R U . . .
C39 C 0.23550(14) 0.70625(15) 0.37741(11) 0.0339(3) Uani 1 1 d . . . . .
H39 H 0.167811 0.680011 0.337368 0.041 Uiso 1 1 calc R U . . .
C37 C 0.44319(13) 0.80796(13) 0.41448(10) 0.0275(3) Uani 1 1 d . . . . .
C17 C 0.11349(14) 0.12989(14) 0.65724(11) 0.0332(3) Uani 1 1 d . . . . .
H17 H 0.104788 0.103601 0.596412 0.040 Uiso 1 1 calc R U . . .
C16 C 0.14808(12) 0.05998(13) 0.70570(11) 0.0321(3) Uani 1 1 d . . . . .
C15 C 0.16325(13) 0.09564(14) 0.79370(11) 0.0325(3) Uani 1 1 d . . . . .
H15 H 0.186798 0.045546 0.825410 0.039 Uiso 1 1 calc R U . . .
C26 C 0.56401(16) 0.47370(15) 0.79433(10) 0.0343(4) Uani 1 1 d . . . . .
H26A H 0.635379 0.537307 0.822364 0.051 Uiso 1 1 calc R U . . .
H26B H 0.586749 0.400353 0.765253 0.051 Uiso 1 1 calc R U . . .
H26C H 0.508226 0.454145 0.837506 0.051 Uiso 1 1 calc R U . . .
C43 C -0.00995(15) 0.59227(18) 0.70038(12) 0.0415(4) Uani 1 1 d . . . . .
C42 C -0.05889(19) 0.6916(2) 0.74261(13) 0.0530(5) Uani 1 1 d . . . . .
H42A H -0.115709 0.703355 0.702285 0.079 Uiso 1 1 calc R U . . .
H42B H 0.005948 0.766842 0.761517 0.079 Uiso 1 1 calc R U . . .
H42C H -0.099821 0.671401 0.792413 0.079 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 0.0181 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
H4OA O4 H4OB 107(2) . . ?
C9 N4 C25 125.00(12) . . ?
C9 N4 H4 119.0(12) . . ?
C25 N4 H4 115.4(12) . . ?
C6 N2 C5 119.02(11) . . ?
H3OB O3 H3OA 101(2) . . ?
C11 N1 C12 121.65(11) . . ?
C11 N1 C13 119.48(11) . . ?
C12 N1 C13 118.81(11) . . ?
C8 N3 C19 127.43(12) . . ?
C8 N3 H3 118.0(12) . . ?
C19 N3 H3 113.4(11) . . ?
C36 N5 C35 123.51(12) . . ?
C36 N5 H5 116.2(13) . . ?
C35 N5 H5 110.1(13) . . ?
N2 C5 C4 118.99(12) . . ?
N2 C5 C12 122.11(12) . . ?
C4 C5 C12 118.90(12) . . ?
C20 C19 C24 119.48(12) . . ?
C20 C19 N3 116.62(12) . . ?
C24 C19 N3 123.72(12) . . ?
N3 C8 C7 124.53(12) . . ?
N3 C8 C9 117.04(11) . . ?
C7 C8 C9 118.42(12) . . ?
N1 C12 C1 122.22(12) . . ?
N1 C12 C5 117.74(12) . . ?
C1 C12 C5 120.04(12) . . ?
C21 C20 C19 120.55(13) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
N4 C25 C26 110.14(11) . . ?
N4 C25 C27 108.67(11) . . ?
C26 C25 C27 112.02(12) . . ?
N4 C25 H25 108.6 . . ?
C26 C25 H25 108.6 . . ?
C27 C25 H25 108.6 . . ?
N1 C11 C10 122.73(12) . . ?
N1 C11 C6 117.12(11) . . ?
C10 C11 C6 120.14(12) . . ?
C31 C30 C35 118.39(13) . . ?
C31 C30 C29 120.06(13) . . ?
C35 C30 C29 121.54(12) . . ?
N2 C6 C7 119.40(12) . . ?
N2 C6 C11 122.35(12) . . ?
C7 C6 C11 118.22(12) . . ?
N4 C9 C10 121.83(12) . . ?
N4 C9 C8 118.97(12) . . ?
C10 C9 C8 119.19(12) . . ?
O2 C28 O1 124.37(13) . . ?
O2 C28 C29 119.56(12) . . ?
O1 C28 C29 116.02(12) . . ?
C2 C1 C12 119.43(13) . . ?
C2 C1 H1 120.3 . . ?
C12 C1 H1 120.3 . . ?
C11 C10 C9 121.23(12) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C8 C7 C6 122.68(12) . . ?
C8 C7 H7 118.7 . . ?
C6 C7 H7 118.7 . . ?
C1 C2 C3 121.13(13) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 H2 119.4 . . ?
C3 C4 C5 120.65(13) . . ?
C3 C4 H4A 119.7 . . ?
C5 C4 H4A 119.7 . . ?
C23 C24 C19 120.19(13) . . ?
C23 C24 H24 119.9 . . ?
C19 C24 H24 119.9 . . ?
C23 C22 C21 121.61(13) . . ?
C23 C22 Cl2 119.80(11) . . ?
C21 C22 Cl2 118.59(11) . . ?
C20 C21 C22 119.00(13) . . ?
C20 C21 H21 120.5 . . ?
C22 C21 H21 120.5 . . ?
C4 C3 C2 119.85(12) . . ?
C4 C3 H3A 120.1 . . ?
C2 C3 H3A 120.1 . . ?
C32 C31 C30 122.06(14) . . ?
C32 C31 H31 119.0 . . ?
C30 C31 H31 119.0 . . ?
C34 C35 C30 119.47(13) . . ?
C34 C35 N5 121.90(13) . . ?
C30 C35 N5 118.60(12) . . ?
C14 C13 C18 122.23(13) . . ?
C14 C13 N1 118.71(13) . . ?
C18 C13 N1 119.05(13) . . ?
N5 C36 C37 122.47(13) . . ?
N5 C36 C41 121.95(13) . . ?
C37 C36 C41 115.44(13) . . ?
C40 C41 C36 123.04(14) . . ?
C40 C41 Cl3 118.49(12) . . ?
C36 C41 Cl3 118.47(11) . . ?
C33 C34 C35 121.01(14) . . ?
C33 C34 H34 119.5 . . ?
C35 C34 H34 119.5 . . ?
C22 C23 C24 119.16(13) . . ?
C22 C23 H23 120.4 . . ?
C24 C23 H23 120.4 . . ?
C39 C38 C37 120.11(15) . . ?
C39 C38 H38 119.9 . . ?
C37 C38 H38 119.9 . . ?
C13 C14 C15 118.82(14) . . ?
C13 C14 H14 120.6 . . ?
C15 C14 H14 120.6 . . ?
C39 C40 C41 119.37(14) . . ?
C39 C40 H40 120.3 . . ?
C41 C40 H40 120.3 . . ?
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 . . ?
C33 C32 C31 119.20(13) . . ?
C33 C32 H32 120.4 . . ?
C31 C32 H32 120.4 . . ?
C32 C33 C34 119.86(14) . . ?
C32 C33 H33 120.1 . . ?
C34 C33 H33 120.1 . . ?
C30 C29 C28 114.59(11) . . ?
C30 C29 H29A 108.6 . . ?
C28 C29 H29A 108.6 . . ?
C30 C29 H29B 108.6 . . ?
C28 C29 H29B 108.6 . . ?
H29A C29 H29B 107.6 . . ?
C13 C18 C17 118.80(14) . . ?
C13 C18 H18 120.6 . . ?
C17 C18 H18 120.6 . . ?
C38 C39 C40 119.71(14) . . ?
C38 C39 H39 120.1 . . ?
C40 C39 H39 120.1 . . ?
C38 C37 C36 122.29(14) . . ?
C38 C37 Cl4 118.25(12) . . ?
C36 C37 Cl4 119.41(11) . . ?
C16 C17 C18 118.84(15) . . ?
C16 C17 H17 120.6 . . ?
C18 C17 H17 120.6 . . ?
C15 C16 C17 122.33(14) . . ?
C15 C16 Cl1 118.06(13) . . ?
C17 C16 Cl1 119.61(13) . . ?
C16 C15 C14 118.97(15) . . ?
C16 C15 H15 120.5 . . ?
C14 C15 H15 120.5 . . ?
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 . . ?
N6 C43 C42 178.7(2) . . ?
C43 C42 H42A 109.5 . . ?
C43 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C43 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
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
Cl2 C22 1.7466(14) . ?
Cl3 C41 1.7389(15) . ?
Cl4 C37 1.7348(15) . ?
Cl1 C16 1.7471(15) . ?
O1 C28 1.2721(17) . ?
O2 C28 1.2386(18) . ?
O4 H4OA 0.85(3) . ?
O4 H4OB 0.92(3) . ?
N4 C9 1.3310(18) . ?
N4 C25 1.4749(17) . ?
N4 H4 0.832(19) . ?
N2 C6 1.3229(17) . ?
N2 C5 1.3653(17) . ?
O3 H3OB 0.85(3) . ?
O3 H3OA 0.88(3) . ?
N1 C11 1.3616(17) . ?
N1 C12 1.3916(17) . ?
N1 C13 1.4580(17) . ?
N3 C8 1.3590(17) . ?
N3 C19 1.4107(17) . ?
N3 H3 0.848(18) . ?
N5 C36 1.3933(19) . ?
N5 C35 1.4138(18) . ?
N5 H5 0.83(2) . ?
C5 C4 1.4127(19) . ?
C5 C12 1.4149(19) . ?
C19 C20 1.3935(19) . ?
C19 C24 1.3963(19) . ?
C8 C7 1.3709(19) . ?
C8 C9 1.4857(18) . ?
C12 C1 1.4064(19) . ?
C20 C21 1.382(2) . ?
C20 H20 0.9500 . ?
C25 C26 1.516(2) . ?
C25 C27 1.5190(19) . ?
C25 H25 1.0000 . ?
C11 C10 1.3819(19) . ?
C11 C6 1.4592(18) . ?
C30 C31 1.390(2) . ?
C30 C35 1.406(2) . ?
C30 C29 1.5075(19) . ?
C6 C7 1.4138(19) . ?
C9 C10 1.4028(19) . ?
C28 C29 1.5327(19) . ?
C1 C2 1.378(2) . ?
C1 H1 0.9500 . ?
C10 H10 0.9500 . ?
C7 H7 0.9500 . ?
C2 C3 1.407(2) . ?
C2 H2 0.9500 . ?
C4 C3 1.371(2) . ?
C4 H4A 0.9500 . ?
C24 C23 1.387(2) . ?
C24 H24 0.9500 . ?
C22 C23 1.381(2) . ?
C22 C21 1.386(2) . ?
C21 H21 0.9500 . ?
C3 H3A 0.9500 . ?
C31 C32 1.386(2) . ?
C31 H31 0.9500 . ?
C35 C34 1.393(2) . ?
C13 C14 1.380(2) . ?
C13 C18 1.381(2) . ?
C36 C37 1.404(2) . ?
C36 C41 1.404(2) . ?
C41 C40 1.386(2) . ?
C34 C33 1.388(2) . ?
C34 H34 0.9500 . ?
C23 H23 0.9500 . ?
C38 C39 1.383(2) . ?
C38 C37 1.386(2) . ?
C38 H38 0.9500 . ?
C14 C15 1.390(2) . ?
C14 H14 0.9500 . ?
N6 C43 1.143(3) . ?
C40 C39 1.384(2) . ?
C40 H40 0.9500 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C32 C33 1.385(2) . ?
C32 H32 0.9500 . ?
C33 H33 0.9500 . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C18 C17 1.390(2) . ?
C18 H18 0.9500 . ?
C39 H39 0.9500 . ?
C17 C16 1.381(2) . ?
C17 H17 0.9500 . ?
C16 C15 1.374(2) . ?
C15 H15 0.9500 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C43 C42 1.458(3) . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?
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 O1 0.848(18) 1.909(19) 2.7532(15) 173.1(16) .
N4 H4 O1 0.832(19) 1.993(19) 2.8068(15) 165.5(16) .
N5 H5 O1 0.83(2) 2.05(2) 2.7940(16) 148.7(17) .
O4 H4OA N2 0.85(3) 2.08(3) 2.9157(16) 168(2) 1_655
O4 H4OB O3 0.92(3) 1.79(3) 2.7060(18) 169(2) .
O3 H3OB O4 0.85(3) 2.00(3) 2.8192(18) 163(2) 2_777
O3 H3OA O2 0.88(3) 1.86(3) 2.7353(17) 177(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
C6 N2 C5 C4 -179.87(12) . . . . ?
C6 N2 C5 C12 -0.47(19) . . . . ?
C8 N3 C19 C20 -140.83(13) . . . . ?
C8 N3 C19 C24 44.1(2) . . . . ?
C19 N3 C8 C7 3.5(2) . . . . ?
C19 N3 C8 C9 -177.26(12) . . . . ?
C11 N1 C12 C1 179.81(12) . . . . ?
C13 N1 C12 C1 2.53(19) . . . . ?
C11 N1 C12 C5 0.21(18) . . . . ?
C13 N1 C12 C5 -177.07(11) . . . . ?
N2 C5 C12 N1 0.64(19) . . . . ?
C4 C5 C12 N1 -179.96(11) . . . . ?
N2 C5 C12 C1 -178.97(12) . . . . ?
C4 C5 C12 C1 0.43(19) . . . . ?
C24 C19 C20 C21 0.35(19) . . . . ?
N3 C19 C20 C21 -174.90(12) . . . . ?
C9 N4 C25 C26 -84.66(16) . . . . ?
C9 N4 C25 C27 152.29(13) . . . . ?
C12 N1 C11 C10 -179.73(12) . . . . ?
C13 N1 C11 C10 -2.47(19) . . . . ?
C12 N1 C11 C6 -1.10(18) . . . . ?
C13 N1 C11 C6 176.15(11) . . . . ?
C5 N2 C6 C7 177.50(11) . . . . ?
C5 N2 C6 C11 -0.51(18) . . . . ?
N1 C11 C6 N2 1.30(19) . . . . ?
C10 C11 C6 N2 179.95(12) . . . . ?
N1 C11 C6 C7 -176.74(11) . . . . ?
C10 C11 C6 C7 1.92(18) . . . . ?
C25 N4 C9 C10 0.6(2) . . . . ?
C25 N4 C9 C8 -178.43(11) . . . . ?
N3 C8 C9 N4 -0.97(18) . . . . ?
C7 C8 C9 N4 178.33(12) . . . . ?
N3 C8 C9 C10 -179.98(12) . . . . ?
C7 C8 C9 C10 -0.68(18) . . . . ?
N1 C12 C1 C2 179.92(12) . . . . ?
C5 C12 C1 C2 -0.49(19) . . . . ?
N1 C11 C10 C9 174.48(12) . . . . ?
C6 C11 C10 C9 -4.1(2) . . . . ?
N4 C9 C10 C11 -175.51(12) . . . . ?
C8 C9 C10 C11 3.47(19) . . . . ?
N3 C8 C7 C6 177.80(12) . . . . ?
C9 C8 C7 C6 -1.45(19) . . . . ?
N2 C6 C7 C8 -177.22(12) . . . . ?
C11 C6 C7 C8 0.87(19) . . . . ?
C12 C1 C2 C3 0.1(2) . . . . ?
N2 C5 C4 C3 179.42(12) . . . . ?
C12 C5 C4 C3 0.00(19) . . . . ?
C20 C19 C24 C23 0.67(19) . . . . ?
N3 C19 C24 C23 175.56(12) . . . . ?
C19 C20 C21 C22 -0.8(2) . . . . ?
C23 C22 C21 C20 0.3(2) . . . . ?
Cl2 C22 C21 C20 -179.71(10) . . . . ?
C5 C4 C3 C2 -0.4(2) . . . . ?
C1 C2 C3 C4 0.3(2) . . . . ?
C35 C30 C31 C32 -1.4(2) . . . . ?
C29 C30 C31 C32 178.43(13) . . . . ?
C31 C30 C35 C34 1.3(2) . . . . ?
C29 C30 C35 C34 -178.52(13) . . . . ?
C31 C30 C35 N5 179.12(13) . . . . ?
C29 C30 C35 N5 -0.7(2) . . . . ?
C36 N5 C35 C34 -15.5(2) . . . . ?
C36 N5 C35 C30 166.81(13) . . . . ?
C11 N1 C13 C14 99.37(15) . . . . ?
C12 N1 C13 C14 -83.29(15) . . . . ?
C11 N1 C13 C18 -81.66(16) . . . . ?
C12 N1 C13 C18 95.68(15) . . . . ?
C35 N5 C36 C37 -62.1(2) . . . . ?
C35 N5 C36 C41 122.38(15) . . . . ?
N5 C36 C41 C40 177.00(13) . . . . ?
C37 C36 C41 C40 1.2(2) . . . . ?
N5 C36 C41 Cl3 -2.76(19) . . . . ?
C37 C36 C41 Cl3 -178.58(10) . . . . ?
C30 C35 C34 C33 -0.3(2) . . . . ?
N5 C35 C34 C33 -178.05(13) . . . . ?
C21 C22 C23 C24 0.7(2) . . . . ?
Cl2 C22 C23 C24 -179.28(10) . . . . ?
C19 C24 C23 C22 -1.2(2) . . . . ?
C18 C13 C14 C15 -1.2(2) . . . . ?
N1 C13 C14 C15 177.75(12) . . . . ?
C36 C41 C40 C39 0.2(2) . . . . ?
Cl3 C41 C40 C39 179.92(11) . . . . ?
C30 C31 C32 C33 0.5(2) . . . . ?
C31 C32 C33 C34 0.5(2) . . . . ?
C35 C34 C33 C32 -0.6(2) . . . . ?
C31 C30 C29 C28 -104.09(15) . . . . ?
C35 C30 C29 C28 75.77(17) . . . . ?
O2 C28 C29 C30 137.23(14) . . . . ?
O1 C28 C29 C30 -45.27(17) . . . . ?
C14 C13 C18 C17 0.0(2) . . . . ?
N1 C13 C18 C17 -178.92(12) . . . . ?
C37 C38 C39 C40 0.1(2) . . . . ?
C41 C40 C39 C38 -0.8(2) . . . . ?
C39 C38 C37 C36 1.3(2) . . . . ?
C39 C38 C37 Cl4 -176.10(12) . . . . ?
N5 C36 C37 C38 -177.72(13) . . . . ?
C41 C36 C37 C38 -1.9(2) . . . . ?
N5 C36 C37 Cl4 -0.31(19) . . . . ?
C41 C36 C37 Cl4 175.49(10) . . . . ?
C13 C18 C17 C16 1.0(2) . . . . ?
C18 C17 C16 C15 -0.9(2) . . . . ?
C18 C17 C16 Cl1 179.31(11) . . . . ?
C17 C16 C15 C14 -0.3(2) . . . . ?
Cl1 C16 C15 C14 179.52(11) . . . . ?
C13 C14 C15 C16 1.3(2) . . . . ?
