#------------------------------------------------------------------------------
#$Date: 2021-02-05 00:57:25 +0200 (Fri, 05 Feb 2021) $
#$Revision: 261597 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/15/7241513.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_7241513
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, 0.491(C H4 O), C0.25 H1.02 O0.25'
_chemical_formula_sum            'C41.75 H35.98 Cl4 N5 O2.75'
_chemical_formula_weight         793.42
_chemical_name_systematic
'N-[(2E)-10-(4-chlorophenyl)-3-[(4-chlorophenyl)amino]-2,10-dihydrophenazin-2-ylidene]propan-2-aminium methanol 2-{2-[(2-chloro-6-methylphenyl)amino]phenyl}acetate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 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                90
_cell_angle_beta                 93.438(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.7209(3)
_cell_length_b                   17.2504(5)
_cell_length_c                   27.8319(7)
_cell_measurement_reflns_used    5538
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      66.2640
_cell_measurement_theta_min      3.1520
_cell_volume                     8013.4(3)
_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      295(2)
_diffrn_detector_area_resol_mean 5.1856
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_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  0.0400
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            23679
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.066
_diffrn_reflns_theta_max         67.066
_diffrn_reflns_theta_min         3.181
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.039
_exptl_absorpt_correction_T_max  0.827
_exptl_absorpt_correction_T_min  0.678
_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            'dark red'
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_description       plate
_exptl_crystal_F_000             3291
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.421
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     519
_refine_ls_number_reflns         7080
_refine_ls_number_restraints     21
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0870
_refine_ls_R_factor_gt           0.0592
_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)+(0.1035P)²+4.0085P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1683
_refine_ls_wR_factor_ref         0.1928
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4722
_reflns_number_total             7080
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce01400a2.cif
_cod_data_source_block           lb0535_CFZ-DCF-MeOH
_cod_depositor_comments
'Adding full bibliography for 7241513--7241524.cif.'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7241513
_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   0.568
_shelx_estimated_absorpt_t_max   0.815
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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_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
Cl3 Cl 0.56672(6) 0.78107(7) 0.32300(4) 0.1024(3) Uani 1 1 d . . . . .
Cl4 Cl 0.83513(7) 0.65653(9) 0.25690(5) 0.1268(5) Uani 1 1 d . . . . .
O1 O 0.56916(13) 0.58936(15) 0.36491(8) 0.0782(6) Uani 1 1 d . . . . .
O2 O 0.55254(18) 0.46495(19) 0.37694(13) 0.1213(11) Uani 1 1 d . . . . .
N5 N 0.69490(16) 0.66169(18) 0.31980(10) 0.0730(7) Uani 1 1 d . . . . .
H5 H 0.650(2) 0.655(2) 0.3251(14) 0.088 Uiso 1 1 d . U . . .
C28 C 0.5940(2) 0.5207(2) 0.36567(12) 0.0771(9) Uani 1 1 d . . . . .
C29 C 0.6801(2) 0.5059(2) 0.35142(15) 0.0877(10) Uani 1 1 d . . . . .
H29A H 0.694846 0.453373 0.360794 0.105 Uiso 1 1 calc R U . . .
H29B H 0.680558 0.508689 0.316633 0.105 Uiso 1 1 calc R U . . .
C30 C 0.74317(18) 0.5598(2) 0.37252(12) 0.0766(9) Uani 1 1 d . . . . .
C31 C 0.7985(2) 0.5355(3) 0.40986(16) 0.1002(13) Uani 1 1 d . . . . .
H31 H 0.793900 0.485756 0.422309 0.120 Uiso 1 1 calc R U . . .
C32 C 0.8585(2) 0.5827(3) 0.42835(17) 0.1072(14) Uani 1 1 d . . . . .
H32 H 0.894088 0.564828 0.452844 0.129 Uiso 1 1 calc R U . . .
C33 C 0.8661(2) 0.6560(3) 0.41073(15) 0.0957(12) Uani 1 1 d . . . . .
H33 H 0.906707 0.688295 0.423267 0.115 Uiso 1 1 calc R U . . .
C34 C 0.81317(19) 0.6822(2) 0.37423(13) 0.0816(9) Uani 1 1 d . . . . .
H34 H 0.818844 0.732070 0.362142 0.098 Uiso 1 1 calc R U . . .
C35 C 0.75132(17) 0.6348(2) 0.35528(11) 0.0695(8) Uani 1 1 d . . . . .
C36 C 0.70433(18) 0.7256(2) 0.29055(11) 0.0706(8) Uani 1 1 d . . . . .
C37 C 0.7660(2) 0.7311(3) 0.25915(13) 0.0906(11) Uani 1 1 d . . . . .
C38 C 0.7709(3) 0.7941(3) 0.22745(16) 0.1136(15) Uani 1 1 d . . . . .
H38 H 0.813088 0.797467 0.207248 0.136 Uiso 1 1 calc R U . . .
C39 C 0.7130(3) 0.8505(3) 0.22652(17) 0.1164(15) Uani 1 1 d . . . . .
H39 H 0.716309 0.892372 0.205722 0.140 Uiso 1 1 calc R U . . .
C40 C 0.6513(3) 0.8458(3) 0.25537(17) 0.1049(13) Uani 1 1 d . . . . .
H40 H 0.611639 0.883734 0.254058 0.126 Uiso 1 1 calc R U . . .
C41 C 0.6474(2) 0.7851(2) 0.28657(12) 0.0782(9) Uani 1 1 d . . . . .
Cl1 Cl -0.04461(10) 0.50202(12) 0.30879(6) 0.1656(7) Uani 1 1 d . . . . .
Cl2 Cl 0.78246(6) 0.64771(8) 0.58895(5) 0.1173(4) Uani 1 1 d . . . . .
N1 N 0.16967(13) 0.62628(15) 0.46614(10) 0.0679(6) Uani 1 1 d . . . . .
N2 N 0.27464(15) 0.67103(15) 0.54344(9) 0.0692(6) Uani 1 1 d . . . . .
N3 N 0.50008(14) 0.60967(17) 0.45290(10) 0.0679(7) Uani 1 1 d . . . . .
H3 H 0.514(2) 0.605(2) 0.4249(13) 0.082 Uiso 1 1 d . U . . .
N4 N 0.39764(16) 0.58019(19) 0.37426(9) 0.0778(8) Uani 1 1 d . . . . .
H4 H 0.451(2) 0.578(2) 0.3731(13) 0.093 Uiso 1 1 d . U . . .
C1 C 0.0563(2) 0.6599(2) 0.51340(15) 0.0838(10) Uani 1 1 d . . . . .
H1 H 0.019874 0.645694 0.488364 0.101 Uiso 1 1 calc R U . . .
C2 C 0.0296(2) 0.6873(2) 0.55615(17) 0.0965(12) Uani 1 1 d . . . . .
H2 H -0.025205 0.691636 0.559680 0.116 Uiso 1 1 calc R U . . .
C3 C 0.0825(2) 0.7084(2) 0.59376(16) 0.0947(12) Uani 1 1 d . . . . .
H3A H 0.063148 0.726643 0.622277 0.114 Uiso 1 1 calc R U . . .
C4 C 0.1635(2) 0.7026(2) 0.58940(13) 0.0827(9) Uani 1 1 d . . . . .
H4A H 0.198868 0.716675 0.614986 0.099 Uiso 1 1 calc R U . . .
C5 C 0.19317(18) 0.67554(19) 0.54627(12) 0.0698(8) Uani 1 1 d . . . . .
C6 C 0.30252(17) 0.64487(17) 0.50287(11) 0.0630(7) Uani 1 1 d . . . . .
C7 C 0.38604(17) 0.63865(19) 0.49932(11) 0.0656(7) Uani 1 1 d . . . . .
H7 H 0.419674 0.651560 0.525943 0.079 Uiso 1 1 calc R U . . .
C8 C 0.41958(16) 0.61436(18) 0.45827(10) 0.0612(7) Uani 1 1 d . . . . .
C9 C 0.36671(16) 0.59661(18) 0.41572(11) 0.0635(7) Uani 1 1 d . . . . .
C10 C 0.28293(17) 0.60019(19) 0.41939(11) 0.0684(8) Uani 1 1 d . . . . .
H10 H 0.248980 0.586988 0.392964 0.082 Uiso 1 1 calc R U . . .
C11 C 0.25093(16) 0.62290(18) 0.46143(11) 0.0642(7) Uani 1 1 d . . . . .
C12 C 0.13857(18) 0.65372(18) 0.50811(12) 0.0700(8) Uani 1 1 d . . . . .
C13 C 0.11656(16) 0.59751(19) 0.42752(12) 0.0686(8) Uani 1 1 d . . . . .
C14 C 0.0962(2) 0.5206(2) 0.42715(15) 0.0878(10) Uani 1 1 d . . . . .
H14 H 0.115496 0.488194 0.451907 0.105 Uiso 1 1 calc R U . . .
C15 C 0.0471(3) 0.4915(3) 0.38988(19) 0.1035(13) Uani 1 1 d . . . . .
H15 H 0.033073 0.439343 0.389458 0.124 Uiso 1 1 calc R U . . .
C16 C 0.0195(2) 0.5385(3) 0.35422(16) 0.0958(12) Uani 1 1 d . . . . .
C17 C 0.0394(2) 0.6154(3) 0.35413(15) 0.0985(12) Uani 1 1 d . . . . .
H17 H 0.019464 0.647233 0.329205 0.118 Uiso 1 1 calc R U . . .
C18 C 0.0890(2) 0.6463(2) 0.39106(14) 0.0844(10) Uani 1 1 d . . . . .
H18 H 0.103308 0.698388 0.391149 0.101 Uiso 1 1 calc R U . . .
C19 C 0.56394(16) 0.62003(18) 0.48797(11) 0.0644(7) Uani 1 1 d . . . . .
C20 C 0.63473(18) 0.6490(2) 0.47165(13) 0.0771(9) Uani 1 1 d . . . . .
H20 H 0.636968 0.663727 0.439610 0.093 Uiso 1 1 calc R U . . .
C21 C 0.7017(2) 0.6563(2) 0.50257(15) 0.0870(10) Uani 1 1 d . . . . .
H21 H 0.749492 0.674377 0.491249 0.104 Uiso 1 1 calc R U . . .
C22 C 0.69781(19) 0.6368(2) 0.54981(14) 0.0825(10) Uani 1 1 d . . . . .
C23 C 0.6279(2) 0.6085(2) 0.56703(13) 0.0860(10) Uani 1 1 d . . . . .
H23 H 0.625833 0.595733 0.599392 0.103 Uiso 1 1 calc R U . . .
C24 C 0.56065(19) 0.5991(2) 0.53573(12) 0.0747(8) Uani 1 1 d . . . . .
H24 H 0.513690 0.578749 0.546881 0.090 Uiso 1 1 calc R U . . .
C25 C 0.3523(2) 0.5762(3) 0.32680(13) 0.0915(11) Uani 1 1 d . . . . .
H25 H 0.309269 0.614838 0.326720 0.110 Uiso 1 1 calc R U . . .
C26 C 0.4091(3) 0.5997(4) 0.28859(15) 0.1256(17) Uani 1 1 d . . . . .
H26A H 0.429506 0.650724 0.295501 0.188 Uiso 1 1 calc R U . . .
H26B H 0.380755 0.599507 0.257548 0.188 Uiso 1 1 calc R U . . .
H26C H 0.452753 0.563556 0.288635 0.188 Uiso 1 1 calc R U . . .
C27 C 0.3153(3) 0.5001(3) 0.31753(18) 0.1260(17) Uani 1 1 d . . . . .
H27A H 0.356282 0.462331 0.312849 0.189 Uiso 1 1 calc R U . . .
H27B H 0.279774 0.502807 0.289160 0.189 Uiso 1 1 calc R U . . .
H27C H 0.285534 0.485232 0.344522 0.189 Uiso 1 1 calc R U . . .
O3A O 0.1162(4) 0.8208(3) 0.37299(19) 0.0923(19) Uani 0.491(6) 1 d D U P A 1
H3OA H 0.115601 0.862440 0.387190 0.138 Uiso 0.491(6) 1 calc R U P A 1
C42A C 0.0490(8) 0.8183(7) 0.3354(5) 0.155(5) Uani 0.491(6) 1 d D U P A 1
H42A H -0.000860 0.826073 0.350119 0.232 Uiso 0.491(6) 1 calc R U P A 1
H42B H 0.048322 0.768695 0.319674 0.232 Uiso 0.491(6) 1 calc R U P A 1
H42C H 0.056096 0.858371 0.312105 0.232 Uiso 0.491(6) 1 calc R U P A 1
O3B O -0.0203(13) 0.8182(11) 0.2854(10) 0.200(8) Uani 0.254(3) 1 d D U P A -1
H3OB H -0.047874 0.840741 0.304378 0.300 Uiso 0.2545 1 calc . U P A -1
C42B C -0.0127(15) 0.8673(17) 0.2419(10) 0.166(10) Uani 0.254(3) 1 d D U P A -1
H42D H -0.001957 0.835008 0.214959 0.248 Uiso 0.2545 1 calc . U P A -1
H42E H 0.030509 0.903439 0.247667 0.248 Uiso 0.2545 1 calc . U P A -1
H42F H -0.061736 0.895229 0.235038 0.248 Uiso 0.2545 1 calc . U P A -1
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'
Cl Cl 0.3639 0.7018 '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'
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
C36 N5 C35 125.5(3) . . ?
C36 N5 H5 112(3) . . ?
C35 N5 H5 116(3) . . ?
O2 C28 O1 123.2(3) . . ?
O2 C28 C29 119.0(4) . . ?
O1 C28 C29 117.8(3) . . ?
C30 C29 C28 116.3(3) . . ?
C30 C29 H29A 108.2 . . ?
C28 C29 H29A 108.2 . . ?
C30 C29 H29B 108.2 . . ?
C28 C29 H29B 108.2 . . ?
H29A C29 H29B 107.4 . . ?
C35 C30 C31 117.2(4) . . ?
C35 C30 C29 121.6(3) . . ?
C31 C30 C29 121.2(4) . . ?
C32 C31 C30 122.2(4) . . ?
C32 C31 H31 118.9 . . ?
C30 C31 H31 118.9 . . ?
C33 C32 C31 119.8(4) . . ?
C33 C32 H32 120.1 . . ?
C31 C32 H32 120.1 . . ?
C32 C33 C34 119.9(4) . . ?
C32 C33 H33 120.1 . . ?
C34 C33 H33 120.1 . . ?
C33 C34 C35 120.8(4) . . ?
C33 C34 H34 119.6 . . ?
C35 C34 H34 119.6 . . ?
C30 C35 C34 120.0(3) . . ?
C30 C35 N5 118.3(3) . . ?
C34 C35 N5 121.6(3) . . ?
N5 C36 C37 122.5(3) . . ?
N5 C36 C41 122.0(3) . . ?
C37 C36 C41 115.2(3) . . ?
C36 C37 C38 121.3(4) . . ?
C36 C37 Cl4 119.4(3) . . ?
C38 C37 Cl4 119.1(3) . . ?
C39 C38 C37 119.5(4) . . ?
C39 C38 H38 120.3 . . ?
C37 C38 H38 120.3 . . ?
C40 C39 C38 120.8(4) . . ?
C40 C39 H39 119.6 . . ?
C38 C39 H39 119.6 . . ?
C39 C40 C41 119.4(4) . . ?
C39 C40 H40 120.3 . . ?
C41 C40 H40 120.3 . . ?
C40 C41 C36 123.8(3) . . ?
C40 C41 Cl3 118.0(3) . . ?
C36 C41 Cl3 118.2(3) . . ?
C11 N1 C12 121.1(3) . . ?
C11 N1 C13 118.9(2) . . ?
C12 N1 C13 120.0(2) . . ?
C6 N2 C5 118.0(3) . . ?
C8 N3 C19 128.7(3) . . ?
C8 N3 H3 116(3) . . ?
C19 N3 H3 115(3) . . ?
C9 N4 C25 125.5(3) . . ?
C9 N4 H4 119(2) . . ?
C25 N4 H4 115(2) . . ?
C2 C1 C12 119.3(4) . . ?
C2 C1 H1 120.4 . . ?
C12 C1 H1 120.4 . . ?
C3 C2 C1 121.3(3) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C4 C3 C2 120.4(4) . . ?
C4 C3 H3A 119.8 . . ?
C2 C3 H3A 119.8 . . ?
C3 C4 C5 120.1(4) . . ?
C3 C4 H4A 120.0 . . ?
C5 C4 H4A 120.0 . . ?
N2 C5 C4 118.1(3) . . ?
N2 C5 C12 122.8(3) . . ?
C4 C5 C12 119.1(3) . . ?
N2 C6 C7 119.1(3) . . ?
N2 C6 C11 123.0(3) . . ?
C7 C6 C11 118.0(3) . . ?
C8 C7 C6 122.6(3) . . ?
C8 C7 H7 118.7 . . ?
C6 C7 H7 118.7 . . ?
N3 C8 C7 124.4(3) . . ?
N3 C8 C9 116.7(2) . . ?
C7 C8 C9 118.7(2) . . ?
N4 C9 C10 120.9(3) . . ?
N4 C9 C8 120.0(3) . . ?
C10 C9 C8 119.0(3) . . ?
C11 C10 C9 120.9(3) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C10 C11 N1 122.1(3) . . ?
C10 C11 C6 120.6(3) . . ?
N1 C11 C6 117.3(3) . . ?
N1 C12 C1 122.4(3) . . ?
N1 C12 C5 117.8(3) . . ?
C1 C12 C5 119.9(3) . . ?
C14 C13 C18 121.0(3) . . ?
C14 C13 N1 118.7(3) . . ?
C18 C13 N1 120.2(3) . . ?
C13 C14 C15 119.7(4) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C16 C15 C14 119.9(4) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C17 121.0(4) . . ?
C15 C16 Cl1 119.5(4) . . ?
C17 C16 Cl1 119.5(4) . . ?
C16 C17 C18 120.3(4) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C13 C18 C17 118.1(4) . . ?
C13 C18 H18 121.0 . . ?
C17 C18 H18 121.0 . . ?
C24 C19 C20 119.6(3) . . ?
C24 C19 N3 124.0(3) . . ?
C20 C19 N3 116.3(3) . . ?
C21 C20 C19 120.4(3) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C22 C21 C20 119.8(3) . . ?
C22 C21 H21 120.1 . . ?
C20 C21 H21 120.1 . . ?
C21 C22 C23 120.9(3) . . ?
C21 C22 Cl2 119.5(3) . . ?
C23 C22 Cl2 119.6(3) . . ?
C22 C23 C24 119.6(3) . . ?
C22 C23 H23 120.2 . . ?
C24 C23 H23 120.2 . . ?
C19 C24 C23 119.6(3) . . ?
C19 C24 H24 120.2 . . ?
C23 C24 H24 120.2 . . ?
C27 C25 N4 112.6(4) . . ?
C27 C25 C26 112.9(4) . . ?
N4 C25 C26 107.6(3) . . ?
C27 C25 H25 107.8 . . ?
N4 C25 H25 107.8 . . ?
C26 C25 H25 107.8 . . ?
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 . . ?
C42A O3A H3OA 109.5 . . ?
O3A C42A O3B 172.1(15) . . ?
O3A C42A H42A 109.5 . . ?
O3B C42A H42A 77.9 . . ?
O3A C42A H42B 109.5 . . ?
O3B C42A H42B 69.5 . . ?
H42A C42A H42B 109.5 . . ?
O3A C42A H42C 109.5 . . ?
O3B C42A H42C 64.4 . . ?
H42A C42A H42C 109.5 . . ?
H42B C42A H42C 109.5 . . ?
C42B O3B C42A 124.0(14) . . ?
C42B O3B H3OB 109.5 . . ?
C42A O3B H3OB 81.9 . . ?
O3B C42B H42D 109.5 . . ?
O3B C42B H42E 109.5 . . ?
H42D C42B H42E 109.5 . . ?
O3B C42B H42F 109.5 . . ?
H42D C42B H42F 109.5 . . ?
H42E C42B H42F 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
Cl3 C41 1.738(4) . ?
Cl4 C37 1.734(4) . ?
O1 C28 1.256(4) . ?
O2 C28 1.236(4) . ?
N5 C36 1.385(4) . ?
N5 C35 1.403(4) . ?
N5 H5 0.79(4) . ?
C28 C29 1.538(5) . ?
C29 C30 1.499(6) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 C35 1.390(5) . ?
C30 C31 1.412(5) . ?
C31 C32 1.369(7) . ?
C31 H31 0.9300 . ?
C32 C33 1.366(7) . ?
C32 H32 0.9300 . ?
C33 C34 1.382(5) . ?
C33 H33 0.9300 . ?
C34 C35 1.397(5) . ?
C34 H34 0.9300 . ?
C36 C37 1.394(4) . ?
C36 C41 1.399(5) . ?
C37 C38 1.404(6) . ?
C38 C39 1.372(7) . ?
C38 H38 0.9300 . ?
C39 C40 1.347(7) . ?
C39 H39 0.9300 . ?
C40 C41 1.365(5) . ?
C40 H40 0.9300 . ?
Cl1 C16 1.727(4) . ?
Cl2 C22 1.744(3) . ?
N1 C11 1.374(4) . ?
N1 C12 1.390(4) . ?
N1 C13 1.441(4) . ?
N2 C6 1.326(4) . ?
N2 C5 1.371(4) . ?
N3 C8 1.366(3) . ?
N3 C19 1.414(4) . ?
N3 H3 0.83(4) . ?
N4 C9 1.323(4) . ?
N4 C25 1.485(4) . ?
N4 H4 0.90(4) . ?
C1 C2 1.379(6) . ?
C1 C12 1.397(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.379(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.370(5) . ?
C3 H3A 0.9300 . ?
C4 C5 1.406(5) . ?
C4 H4A 0.9300 . ?
C5 C12 1.410(5) . ?
C6 C7 1.410(4) . ?
C6 C11 1.448(4) . ?
C7 C8 1.368(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.467(4) . ?
C9 C10 1.412(4) . ?
C10 C11 1.373(4) . ?
C10 H10 0.9300 . ?
C13 C14 1.369(5) . ?
C13 C18 1.376(5) . ?
C14 C15 1.379(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.342(7) . ?
C15 H15 0.9300 . ?
C16 C17 1.367(7) . ?
C17 C18 1.388(6) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C24 1.382(5) . ?
C19 C20 1.387(4) . ?
C20 C21 1.377(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.362(6) . ?
C21 H21 0.9300 . ?
C22 C23 1.379(5) . ?
C23 C24 1.391(5) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 C27 1.469(7) . ?
C25 C26 1.522(6) . ?
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 . ?
O3A C42A 1.491(13) . ?
O3A H3OA 0.8200 . ?
C42A O3B 1.76(2) . ?
C42A H42A 0.9600 . ?
C42A H42B 0.9600 . ?
C42A H42C 0.9600 . ?
O3B C42B 1.489(16) . ?
O3B H3OB 0.8200 . ?
C42B H42D 0.9600 . ?
C42B H42E 0.9600 . ?
C42B H42F 0.9600 . ?
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 0.83(4) 1.98(4) 2.792(3) 168(4) .
N4 H4 O1 0.90(4) 2.00(4) 2.899(3) 171(4) .
N4 H4 O2 0.90(4) 2.58(4) 3.262(4) 133(3) .
N5 H5 O1 0.79(4) 2.13(4) 2.805(3) 145(4) .
O3A H3OA O2 0.82 2.07 2.710(6) 134.7 3_455
C18 H18 O3A 0.93 2.19 3.091(6) 164.2 .
C24 H24 O2 0.93 2.56 3.356(5) 143.3 5_666
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
O2 C28 C29 C30 -135.6(4) . . . . ?
O1 C28 C29 C30 44.9(5) . . . . ?
C28 C29 C30 C35 -75.9(4) . . . . ?
C28 C29 C30 C31 106.0(4) . . . . ?
C35 C30 C31 C32 -0.8(5) . . . . ?
C29 C30 C31 C32 177.3(4) . . . . ?
C30 C31 C32 C33 0.3(6) . . . . ?
C31 C32 C33 C34 -0.2(6) . . . . ?
C32 C33 C34 C35 0.6(6) . . . . ?
C31 C30 C35 C34 1.2(4) . . . . ?
C29 C30 C35 C34 -176.9(3) . . . . ?
C31 C30 C35 N5 -177.0(3) . . . . ?
C29 C30 C35 N5 4.9(4) . . . . ?
C33 C34 C35 C30 -1.1(5) . . . . ?
C33 C34 C35 N5 177.0(3) . . . . ?
C36 N5 C35 C30 -163.0(3) . . . . ?
C36 N5 C35 C34 18.8(5) . . . . ?
C35 N5 C36 C37 60.3(5) . . . . ?
C35 N5 C36 C41 -127.0(4) . . . . ?
N5 C36 C37 C38 175.5(4) . . . . ?
C41 C36 C37 C38 2.3(6) . . . . ?
N5 C36 C37 Cl4 -1.2(5) . . . . ?
C41 C36 C37 Cl4 -174.3(3) . . . . ?
C36 C37 C38 C39 -1.5(7) . . . . ?
Cl4 C37 C38 C39 175.2(4) . . . . ?
C37 C38 C39 C40 -0.5(8) . . . . ?
C38 C39 C40 C41 1.3(8) . . . . ?
C39 C40 C41 C36 -0.3(7) . . . . ?
C39 C40 C41 Cl3 -179.8(4) . . . . ?
N5 C36 C41 C40 -174.6(4) . . . . ?
C37 C36 C41 C40 -1.5(6) . . . . ?
N5 C36 C41 Cl3 4.8(5) . . . . ?
C37 C36 C41 Cl3 178.0(3) . . . . ?
C12 C1 C2 C3 -0.2(6) . . . . ?
C1 C2 C3 C4 0.1(6) . . . . ?
C2 C3 C4 C5 0.4(6) . . . . ?
C6 N2 C5 C4 179.5(3) . . . . ?
C6 N2 C5 C12 0.0(5) . . . . ?
C3 C4 C5 N2 179.7(3) . . . . ?
C3 C4 C5 C12 -0.7(5) . . . . ?
C5 N2 C6 C7 -179.1(3) . . . . ?
C5 N2 C6 C11 1.5(4) . . . . ?
N2 C6 C7 C8 -178.0(3) . . . . ?
C11 C6 C7 C8 1.3(5) . . . . ?
C19 N3 C8 C7 7.2(5) . . . . ?
C19 N3 C8 C9 -176.8(3) . . . . ?
C6 C7 C8 N3 178.0(3) . . . . ?
C6 C7 C8 C9 2.1(5) . . . . ?
C25 N4 C9 C10 10.2(5) . . . . ?
C25 N4 C9 C8 -167.5(3) . . . . ?
N3 C8 C9 N4 -2.7(4) . . . . ?
C7 C8 C9 N4 173.5(3) . . . . ?
N3 C8 C9 C10 179.7(3) . . . . ?
C7 C8 C9 C10 -4.1(5) . . . . ?
N4 C9 C10 C11 -175.1(3) . . . . ?
C8 C9 C10 C11 2.6(5) . . . . ?
C9 C10 C11 N1 -179.4(3) . . . . ?
C9 C10 C11 C6 0.9(5) . . . . ?
C12 N1 C11 C10 -176.2(3) . . . . ?
C13 N1 C11 C10 6.6(5) . . . . ?
C12 N1 C11 C6 3.4(4) . . . . ?
C13 N1 C11 C6 -173.8(3) . . . . ?
N2 C6 C11 C10 176.4(3) . . . . ?
C7 C6 C11 C10 -3.0(5) . . . . ?
N2 C6 C11 N1 -3.2(4) . . . . ?
C7 C6 C11 N1 177.4(3) . . . . ?
C11 N1 C12 C1 178.1(3) . . . . ?
C13 N1 C12 C1 -4.7(5) . . . . ?
C11 N1 C12 C5 -2.1(4) . . . . ?
C13 N1 C12 C5 175.1(3) . . . . ?
C2 C1 C12 N1 179.7(3) . . . . ?
C2 C1 C12 C5 -0.1(5) . . . . ?
N2 C5 C12 N1 0.3(5) . . . . ?
C4 C5 C12 N1 -179.2(3) . . . . ?
N2 C5 C12 C1 -179.9(3) . . . . ?
C4 C5 C12 C1 0.6(5) . . . . ?
C11 N1 C13 C14 87.9(4) . . . . ?
C12 N1 C13 C14 -89.3(4) . . . . ?
C11 N1 C13 C18 -90.1(4) . . . . ?
C12 N1 C13 C18 92.7(4) . . . . ?
C18 C13 C14 C15 -0.4(6) . . . . ?
N1 C13 C14 C15 -178.4(3) . . . . ?
C13 C14 C15 C16 0.0(6) . . . . ?
C14 C15 C16 C17 0.0(7) . . . . ?
C14 C15 C16 Cl1 -177.9(3) . . . . ?
C15 C16 C17 C18 0.3(6) . . . . ?
Cl1 C16 C17 C18 178.2(3) . . . . ?
C14 C13 C18 C17 0.7(5) . . . . ?
N1 C13 C18 C17 178.7(3) . . . . ?
C16 C17 C18 C13 -0.7(5) . . . . ?
C8 N3 C19 C24 34.1(5) . . . . ?
C8 N3 C19 C20 -149.7(3) . . . . ?
C24 C19 C20 C21 0.7(5) . . . . ?
N3 C19 C20 C21 -175.7(3) . . . . ?
C19 C20 C21 C22 -1.8(6) . . . . ?
C20 C21 C22 C23 1.3(6) . . . . ?
C20 C21 C22 Cl2 -178.9(3) . . . . ?
C21 C22 C23 C24 0.5(6) . . . . ?
Cl2 C22 C23 C24 -179.4(3) . . . . ?
C20 C19 C24 C23 1.1(5) . . . . ?
N3 C19 C24 C23 177.2(3) . . . . ?
C22 C23 C24 C19 -1.6(5) . . . . ?
C9 N4 C25 C27 -85.3(5) . . . . ?
C9 N4 C25 C26 149.6(4) . . . . ?
