# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 2099748'
loop_
_audit_author_name
_audit_author_address
'Petra Bombicz'
;Research Centre for Natural Sciences
Hungary
;
_audit_update_record             
;
2021-07-27 deposited with the CCDC.	2021-08-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
4-chloro-N-(2,6-dimethylpiperidin-1-yl)-3-sulfamoylbenzamide
;
_chemical_name_common            'Clopamide anhydrate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H20 Cl N3 O3 S'
_chemical_formula_sum            'C14 H20 Cl N3 O3 S'
_chemical_formula_weight         345.84

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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   18.7914(4)
_cell_length_b                   9.2921(4)
_cell_length_c                   19.0621(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.32
_cell_angle_gamma                90
_cell_volume                     3284.51(17)
_cell_formula_units_Z            8
_cell_measurement_temperature    128(2)
_cell_measurement_reflns_used    33523
_cell_measurement_theta_min      3.065
_cell_measurement_theta_max      68.255

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'Not measured'
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_F_000             1456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    3.389
_shelx_estimated_absorpt_T_min   0.282
_shelx_estimated_absorpt_T_max   0.728
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.919
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_process_details   
;
NUMABS; Higashi, 2002
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      128(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'NORMAL-focus sealed tube'
_diffrn_radiation_monochromator  Graphite
_diffrn_radiation_detector       RX
_diffrn_measurement_device_type  R-AXIS-RAPID
_diffrn_measurement_method       dtprofit.ref
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            42764
_diffrn_reflns_av_unetI/netI     0.0630
_diffrn_reflns_av_R_equivalents  0.0740
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.063
_diffrn_reflns_theta_max         68.225
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             5936
_reflns_number_gt                5038
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Crystal Clear (Rigaku/MSC, 2005)'
_computing_cell_refinement       'Crystal Clear (Rigaku/MSC, 2005)'
_computing_data_reduction        'Crystal Clear (Rigaku/MSC, 2005)'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2006)'
_computing_publication_material  
;
MERCURY (Macrae et al., 2006); Platon (Spek,
 2009
;
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0389P)²+27.7443P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5936
_refine_ls_number_parameters     401
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1199
_refine_ls_R_factor_gt           0.0998
_refine_ls_wR_factor_ref         0.2344
_refine_ls_wR_factor_gt          0.2258
_refine_ls_goodness_of_fit_ref   1.229
_refine_ls_restrained_S_all      1.229
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 1.02997(9) 0.4007(2) 0.36783(10) 0.0387(5) Uani 1 1 d . . . . .
S1 S 0.88441(9) 0.4486(2) 0.44199(9) 0.0267(4) Uani 1 1 d . . . . .
O1 O 0.8116(3) 0.4463(6) 0.4527(2) 0.0331(12) Uani 1 1 d . . . . .
O2 O 0.9359(3) 0.3673(6) 0.4893(3) 0.0357(13) Uani 1 1 d . . . . .
O3 O 0.7255(3) 0.1687(6) 0.1642(3) 0.0395(13) Uani 1 1 d . . . . .
N1 N 0.9120(3) 0.6115(7) 0.4435(3) 0.0303(14) Uani 1 1 d . . . . .
H1NA H 0.9605 0.6007 0.4521 0.036 Uiso 1 1 d R U . . .
H1NB H 0.8934 0.6687 0.4064 0.036 Uiso 1 1 d R U . . .
N8 N 0.6877(3) 0.3775(7) 0.2085(3) 0.0260(13) Uani 1 1 d . . . . .
H8 H 0.7002 0.4538 0.2349 0.031 Uiso 1 1 d R U . . .
N9 N 0.6152(3) 0.3630(7) 0.1735(3) 0.0263(13) Uani 1 1 d . . . . .
C1 C 0.8159(4) 0.3560(8) 0.3138(3) 0.0233(15) Uani 1 1 d . . . . .
H1 H 0.7738 0.3756 0.3337 0.028 Uiso 1 1 calc R U . . .
C2 C 0.8827(4) 0.3812(8) 0.3538(4) 0.0272(16) Uani 1 1 d . . . . .
C3 C 0.9448(4) 0.3595(8) 0.3227(4) 0.0280(16) Uani 1 1 d . . . . .
C4 C 0.9384(4) 0.3056(8) 0.2543(4) 0.0289(16) Uani 1 1 d . . . . .
H4 H 0.9804 0.2896 0.2336 0.035 Uiso 1 1 calc R U . . .
C5 C 0.8715(4) 0.2751(8) 0.2161(4) 0.0270(16) Uani 1 1 d . . . . .
H5 H 0.8675 0.2350 0.1698 0.032 Uiso 1 1 calc R U . . .
C6 C 0.8092(4) 0.3029(8) 0.2456(3) 0.0267(16) Uani 1 1 d . . . . .
C7 C 0.7370(4) 0.2767(8) 0.2018(4) 0.0261(16) Uani 1 1 d . . . . .
C10 C 0.5969(4) 0.4921(8) 0.1291(4) 0.0275(16) Uani 1 1 d . . . . .
H10 H 0.6048 0.5793 0.1601 0.033 Uiso 1 1 calc R U . . .
C11 C 0.5181(4) 0.4866(9) 0.0950(4) 0.0334(18) Uani 1 1 d . . . . .
H11A H 0.5108 0.4049 0.0613 0.040 Uiso 1 1 calc R U . . .
H11B H 0.5058 0.5762 0.0677 0.040 Uiso 1 1 calc R U . . .
C12 C 0.4676(4) 0.4696(9) 0.1495(4) 0.0368(19) Uani 1 1 d . . . . .
H12A H 0.4697 0.5570 0.1795 0.044 Uiso 1 1 calc R U . . .
H12B H 0.4174 0.4577 0.1248 0.044 Uiso 1 1 calc R U . . .
C13 C 0.4896(4) 0.3393(9) 0.1959(4) 0.0355(18) Uani 1 1 d . . . . .
H13A H 0.4820 0.2507 0.1668 0.043 Uiso 1 1 calc R U . . .
H13B H 0.4591 0.3330 0.2336 0.043 Uiso 1 1 calc R U . . .
C14 C 0.5691(4) 0.3503(9) 0.2300(4) 0.0315(17) Uani 1 1 d . . . . .
H14 H 0.5757 0.4388 0.2602 0.038 Uiso 1 1 calc R U . . .
C15 C 0.5904(4) 0.2198(9) 0.2770(4) 0.040(2) Uani 1 1 d . . . . .
H15A H 0.5828 0.1320 0.2483 0.060 Uiso 1 1 calc R U . . .
H15B H 0.5608 0.2162 0.3148 0.060 Uiso 1 1 calc R U . . .
H15C H 0.6414 0.2271 0.2982 0.060 Uiso 1 1 calc R U . . .
C16 C 0.6451(4) 0.5016(10) 0.0728(4) 0.044(2) Uani 1 1 d . . . . .
H16A H 0.6956 0.5069 0.0957 0.066 Uiso 1 1 calc R U . . .
H16B H 0.6328 0.5879 0.0438 0.066 Uiso 1 1 calc R U . . .
H16C H 0.6381 0.4161 0.0423 0.066 Uiso 1 1 calc R U . . .
Cl2 Cl 0.12767(10) 0.1322(2) -0.02834(9) 0.0360(5) Uani 1 1 d . . . . .
S2 S 0.05133(9) 0.0783(2) 0.11370(8) 0.0238(4) Uani 1 1 d . . . . .
O4 O 0.0374(2) 0.0876(6) 0.1848(2) 0.0299(12) Uani 1 1 d . . . . .
O5 O 0.0026(2) 0.1490(5) 0.0590(2) 0.0286(11) Uani 1 1 d . . . . .
O6 O 0.3321(3) 0.3613(6) 0.2724(3) 0.0353(13) Uani 1 1 d . . . . .
N2 N 0.0553(3) -0.0879(6) 0.0917(3) 0.0267(13) Uani 1 1 d . . . . .
H2NA H 0.0901 -0.1466 0.1153 0.032 Uiso 1 1 d R U . . .
H2NB H 0.0439 -0.1056 0.0442 0.032 Uiso 1 1 d R U . . .
N28 N 0.2862(3) 0.1550(7) 0.3113(3) 0.0264(13) Uani 1 1 d . . . . .
H28 H 0.2584 0.0798 0.2993 0.032 Uiso 1 1 d R U . . .
N29 N 0.3224(3) 0.1687(6) 0.3819(3) 0.0249(13) Uani 1 1 d . . . . .
C21 C 0.1794(3) 0.1766(7) 0.1824(3) 0.0224(15) Uani 1 1 d . . . . .
H21 H 0.1576 0.1615 0.2235 0.027 Uiso 1 1 calc R U . . .
C22 C 0.1399(4) 0.1488(8) 0.1161(4) 0.0259(15) Uani 1 1 d . . . . .
C23 C 0.1723(4) 0.1675(8) 0.0566(3) 0.0265(16) Uani 1 1 d . . . . .
C24 C 0.2428(4) 0.2207(8) 0.0635(4) 0.0281(16) Uani 1 1 d . . . . .
H24 H 0.2642 0.2378 0.0224 0.034 Uiso 1 1 calc R U . . .
C25 C 0.2809(4) 0.2481(8) 0.1298(4) 0.0271(16) Uani 1 1 d . . . . .
H25 H 0.3291 0.2825 0.1346 0.033 Uiso 1 1 calc R U . . .
C26 C 0.2492(4) 0.2256(8) 0.1905(4) 0.0265(16) Uani 1 1 d . . . . .
C27 C 0.2934(3) 0.2551(8) 0.2621(4) 0.0251(15) Uani 1 1 d . . . . .
C30 C 0.3671(4) 0.0365(8) 0.3983(4) 0.0285(16) Uani 1 1 d . . . . .
H30 H 0.3348 -0.0496 0.3916 0.034 Uiso 1 1 calc R U . . .
C31 C 0.4038(4) 0.0425(9) 0.4760(4) 0.0358(18) Uani 1 1 d . . . . .
H31A H 0.4307 -0.0480 0.4881 0.043 Uiso 1 1 calc R U . . .
H31B H 0.4389 0.1227 0.4821 0.043 Uiso 1 1 calc R U . . .
C32 C 0.3504(5) 0.0634(10) 0.5269(4) 0.046(2) Uani 1 1 d . . . . .
H32A H 0.3765 0.0722 0.5762 0.056 Uiso 1 1 calc R U . . .
H32B H 0.3178 -0.0207 0.5247 0.056 Uiso 1 1 calc R U . . .
C33 C 0.3068(4) 0.1991(9) 0.5064(4) 0.0355(18) Uani 1 1 d . . . . .
H33A H 0.3393 0.2836 0.5113 0.043 Uiso 1 1 calc R U . . .
H33B H 0.2710 0.2125 0.5387 0.043 Uiso 1 1 calc R U . . .
C34 C 0.2678(4) 0.1881(9) 0.4296(4) 0.0310(17) Uani 1 1 d . . . . .
H34 H 0.2353 0.1022 0.4253 0.037 Uiso 1 1 calc R U . . .
C35 C 0.2232(4) 0.3208(9) 0.4085(4) 0.042(2) Uani 1 1 d . . . . .
H35A H 0.2550 0.4046 0.4095 0.063 Uiso 1 1 calc R U . . .
H35B H 0.1893 0.3358 0.4418 0.063 Uiso 1 1 calc R U . . .
H35C H 0.1963 0.3083 0.3603 0.063 Uiso 1 1 calc R U . . .
C36 C 0.4227(4) 0.0229(9) 0.3498(4) 0.0367(19) Uani 1 1 d . . . . .
H36A H 0.3985 0.0046 0.3011 0.055 Uiso 1 1 calc R U . . .
H36B H 0.4553 -0.0571 0.3658 0.055 Uiso 1 1 calc R U . . .
H36C H 0.4505 0.1124 0.3510 0.055 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 C3 1.733(7) . ?
S1 O1 1.416(5) . ?
S1 O2 1.427(5) . ?
S1 N1 1.599(6) . ?
S1 C2 1.790(7) . ?
O3 C7 1.232(8) . ?
N1 H1NA 0.9066 . ?
N1 H1NB 0.9072 . ?
N8 C7 1.339(9) . ?
N8 N9 1.423(7) . ?
N8 H8 0.8799 . ?
N9 C10 1.475(9) . ?
N9 C14 1.492(9) . ?
C1 C6 1.377(9) . ?
C1 C2 1.378(9) . ?
C1 H1 0.9500 . ?
C2 C3 1.406(10) . ?
C3 C4 1.383(10) . ?
C4 C5 1.377(9) . ?
C4 H4 0.9500 . ?
C5 C6 1.402(9) . ?
C5 H5 0.9500 . ?
C6 C7 1.493(9) . ?
C10 C16 1.516(10) . ?
C10 C11 1.518(9) . ?
C10 H10 1.0000 . ?
C11 C12 1.525(10) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.517(11) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.534(10) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.523(11) . ?
C14 H14 1.0000 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
Cl2 C23 1.730(7) . ?
S2 O4 1.425(5) . ?
S2 O5 1.431(5) . ?
S2 N2 1.605(6) . ?
S2 C22 1.782(7) . ?
O6 C27 1.222(8) . ?
N2 H2NA 0.9124 . ?
N2 H2NB 0.9120 . ?
N28 C27 1.344(9) . ?
N28 N29 1.412(7) . ?
N28 H28 0.8801 . ?
N29 C34 1.488(9) . ?
N29 C30 1.493(9) . ?
C21 C26 1.374(9) . ?
C21 C22 1.383(9) . ?
C21 H21 0.9500 . ?
C22 C23 1.382(10) . ?
C23 C24 1.400(10) . ?
C24 C25 1.372(9) . ?
C24 H24 0.9500 . ?
C25 C26 1.400(9) . ?
C25 H25 0.9500 . ?
C26 C27 1.503(9) . ?
C30 C36 1.508(10) . ?
C30 C31 1.531(10) . ?
C30 H30 1.0000 . ?
C31 C32 1.517(11) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 C33 1.520(12) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.529(10) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 C35 1.509(11) . ?
C34 H34 1.0000 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?

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
O1 S1 O2 118.2(3) . . ?
O1 S1 N1 109.2(3) . . ?
O2 S1 N1 107.8(3) . . ?
O1 S1 C2 105.1(3) . . ?
O2 S1 C2 108.4(3) . . ?
N1 S1 C2 107.7(3) . . ?
S1 N1 H1NA 102.2 . . ?
S1 N1 H1NB 117.2 . . ?
H1NA N1 H1NB 117.1 . . ?
C7 N8 N9 120.9(6) . . ?
C7 N8 H8 119.5 . . ?
N9 N8 H8 119.5 . . ?
N8 N9 C10 107.9(5) . . ?
N8 N9 C14 107.0(5) . . ?
C10 N9 C14 111.7(6) . . ?
C6 C1 C2 121.3(6) . . ?
C6 C1 H1 119.4 . . ?
C2 C1 H1 119.4 . . ?
C1 C2 C3 119.0(6) . . ?
C1 C2 S1 117.1(5) . . ?
C3 C2 S1 123.8(5) . . ?
C4 C3 C2 119.9(6) . . ?
C4 C3 Cl1 118.7(5) . . ?
C2 C3 Cl1 121.4(5) . . ?
C5 C4 C3 120.3(6) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 120.1(6) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C5 119.3(6) . . ?
C1 C6 C7 121.5(6) . . ?
C5 C6 C7 119.2(6) . . ?
O3 C7 N8 124.5(6) . . ?
O3 C7 C6 121.1(7) . . ?
N8 C7 C6 114.4(6) . . ?
N9 C10 C16 110.0(6) . . ?
N9 C10 C11 109.8(6) . . ?
C16 C10 C11 110.6(6) . . ?
N9 C10 H10 108.8 . . ?
C16 C10 H10 108.8 . . ?
C11 C10 H10 108.8 . . ?
C10 C11 C12 112.5(6) . . ?
C10 C11 H11A 109.1 . . ?
C12 C11 H11A 109.1 . . ?
C10 C11 H11B 109.1 . . ?
C12 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?
C13 C12 C11 109.9(7) . . ?
C13 C12 H12A 109.7 . . ?
C11 C12 H12A 109.7 . . ?
C13 C12 H12B 109.7 . . ?
C11 C12 H12B 109.7 . . ?
H12A C12 H12B 108.2 . . ?
C12 C13 C14 110.3(6) . . ?
C12 C13 H13A 109.6 . . ?
C14 C13 H13A 109.6 . . ?
C12 C13 H13B 109.6 . . ?
C14 C13 H13B 109.6 . . ?
H13A C13 H13B 108.1 . . ?
N9 C14 C15 111.1(6) . . ?
N9 C14 C13 109.9(6) . . ?
C15 C14 C13 109.9(6) . . ?
N9 C14 H14 108.6 . . ?
C15 C14 H14 108.6 . . ?
C13 C14 H14 108.6 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C10 C16 H16A 109.5 . . ?
C10 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C10 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O4 S2 O5 118.1(3) . . ?
O4 S2 N2 109.3(3) . . ?
O5 S2 N2 107.6(3) . . ?
O4 S2 C22 105.6(3) . . ?
O5 S2 C22 109.6(3) . . ?
N2 S2 C22 106.1(3) . . ?
S2 N2 H2NA 120.4 . . ?
S2 N2 H2NB 114.8 . . ?
H2NA N2 H2NB 114.7 . . ?
C27 N28 N29 121.1(6) . . ?
C27 N28 H28 119.5 . . ?
N29 N28 H28 119.5 . . ?
N28 N29 C34 108.7(5) . . ?
N28 N29 C30 107.0(5) . . ?
C34 N29 C30 113.1(6) . . ?
C26 C21 C22 121.7(6) . . ?
C26 C21 H21 119.2 . . ?
C22 C21 H21 119.2 . . ?
C23 C22 C21 119.0(6) . . ?
C23 C22 S2 124.0(5) . . ?
C21 C22 S2 116.9(5) . . ?
C22 C23 C24 120.2(6) . . ?
C22 C23 Cl2 122.2(5) . . ?
C24 C23 Cl2 117.6(5) . . ?
C25 C24 C23 119.8(6) . . ?
C25 C24 H24 120.1 . . ?
C23 C24 H24 120.1 . . ?
C24 C25 C26 120.3(6) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
C21 C26 C25 118.9(6) . . ?
C21 C26 C27 122.7(6) . . ?
C25 C26 C27 118.4(6) . . ?
O6 C27 N28 124.8(6) . . ?
O6 C27 C26 121.4(6) . . ?
N28 C27 C26 113.8(6) . . ?
N29 C30 C36 111.3(6) . . ?
N29 C30 C31 108.8(6) . . ?
C36 C30 C31 110.4(6) . . ?
N29 C30 H30 108.8 . . ?
C36 C30 H30 108.8 . . ?
C31 C30 H30 108.8 . . ?
C32 C31 C30 112.6(6) . . ?
C32 C31 H31A 109.1 . . ?
C30 C31 H31A 109.1 . . ?
C32 C31 H31B 109.1 . . ?
C30 C31 H31B 109.1 . . ?
H31A C31 H31B 107.8 . . ?
C31 C32 C33 109.0(7) . . ?
C31 C32 H32A 109.9 . . ?
C33 C32 H32A 109.9 . . ?
C31 C32 H32B 109.9 . . ?
C33 C32 H32B 109.9 . . ?
H32A C32 H32B 108.3 . . ?
C32 C33 C34 110.2(6) . . ?
C32 C33 H33A 109.6 . . ?
C34 C33 H33A 109.6 . . ?
C32 C33 H33B 109.6 . . ?
C34 C33 H33B 109.6 . . ?
H33A C33 H33B 108.1 . . ?
N29 C34 C35 110.1(6) . . ?
N29 C34 C33 108.8(6) . . ?
C35 C34 C33 111.1(6) . . ?
N29 C34 H34 108.9 . . ?
C35 C34 H34 108.9 . . ?
C33 C34 H34 108.9 . . ?
C34 C35 H35A 109.5 . . ?
C34 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C34 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C30 C36 H36A 109.5 . . ?
C30 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C30 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?

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
C7 N8 N9 C10 -124.0(7) . . . . ?
C7 N8 N9 C14 115.7(7) . . . . ?
C6 C1 C2 C3 3.5(11) . . . . ?
C6 C1 C2 S1 -179.4(6) . . . . ?
O1 S1 C2 C1 6.0(7) . . . . ?
O2 S1 C2 C1 133.2(6) . . . . ?
N1 S1 C2 C1 -110.4(6) . . . . ?
O1 S1 C2 C3 -177.0(6) . . . . ?
O2 S1 C2 C3 -49.8(7) . . . . ?
N1 S1 C2 C3 66.6(7) . . . . ?
C1 C2 C3 C4 -3.7(11) . . . . ?
S1 C2 C3 C4 179.3(6) . . . . ?
C1 C2 C3 Cl1 175.6(6) . . . . ?
S1 C2 C3 Cl1 -1.3(10) . . . . ?
C2 C3 C4 C5 0.9(11) . . . . ?
Cl1 C3 C4 C5 -178.4(6) . . . . ?
C3 C4 C5 C6 2.1(11) . . . . ?
C2 C1 C6 C5 -0.5(11) . . . . ?
C2 C1 C6 C7 -179.4(7) . . . . ?
C4 C5 C6 C1 -2.4(11) . . . . ?
C4 C5 C6 C7 176.6(7) . . . . ?
N9 N8 C7 O3 2.6(11) . . . . ?
N9 N8 C7 C6 -176.1(6) . . . . ?
C1 C6 C7 O3 -139.1(8) . . . . ?
C5 C6 C7 O3 42.0(11) . . . . ?
C1 C6 C7 N8 39.7(10) . . . . ?
C5 C6 C7 N8 -139.2(7) . . . . ?
N8 N9 C10 C16 62.3(7) . . . . ?
C14 N9 C10 C16 179.6(6) . . . . ?
N8 N9 C10 C11 -175.7(5) . . . . ?
C14 N9 C10 C11 -58.4(7) . . . . ?
N9 C10 C11 C12 55.6(8) . . . . ?
C16 C10 C11 C12 177.2(7) . . . . ?
C10 C11 C12 C13 -54.3(9) . . . . ?
C11 C12 C13 C14 54.8(8) . . . . ?
N8 N9 C14 C15 -60.0(7) . . . . ?
C10 N9 C14 C15 -177.9(6) . . . . ?
N8 N9 C14 C13 178.1(6) . . . . ?
C10 N9 C14 C13 60.3(8) . . . . ?
C12 C13 C14 N9 -58.0(8) . . . . ?
C12 C13 C14 C15 179.4(6) . . . . ?
C27 N28 N29 C34 114.4(7) . . . . ?
C27 N28 N29 C30 -123.1(7) . . . . ?
C26 C21 C22 C23 1.6(11) . . . . ?
C26 C21 C22 S2 177.4(6) . . . . ?
O4 S2 C22 C23 -175.7(6) . . . . ?
O5 S2 C22 C23 -47.5(7) . . . . ?
N2 S2 C22 C23 68.4(7) . . . . ?
O4 S2 C22 C21 8.8(7) . . . . ?
O5 S2 C22 C21 136.9(5) . . . . ?
N2 S2 C22 C21 -107.1(6) . . . . ?
C21 C22 C23 C24 -3.1(11) . . . . ?
S2 C22 C23 C24 -178.6(6) . . . . ?
C21 C22 C23 Cl2 178.8(6) . . . . ?
S2 C22 C23 Cl2 3.3(10) . . . . ?
C22 C23 C24 C25 3.0(11) . . . . ?
Cl2 C23 C24 C25 -178.9(6) . . . . ?
C23 C24 C25 C26 -1.2(11) . . . . ?
C22 C21 C26 C25 0.2(11) . . . . ?
C22 C21 C26 C27 -179.4(7) . . . . ?
C24 C25 C26 C21 -0.4(11) . . . . ?
C24 C25 C26 C27 179.2(7) . . . . ?
N29 N28 C27 O6 2.2(10) . . . . ?
N29 N28 C27 C26 -178.1(6) . . . . ?
C21 C26 C27 O6 -138.3(7) . . . . ?
C25 C26 C27 O6 42.1(10) . . . . ?
C21 C26 C27 N28 42.1(9) . . . . ?
C25 C26 C27 N28 -137.5(7) . . . . ?
N28 N29 C30 C36 61.6(7) . . . . ?
C34 N29 C30 C36 -178.7(6) . . . . ?
N28 N29 C30 C31 -176.5(6) . . . . ?
C34 N29 C30 C31 -56.8(7) . . . . ?
N29 C30 C31 C32 54.8(9) . . . . ?
C36 C30 C31 C32 177.2(7) . . . . ?
C30 C31 C32 C33 -56.4(9) . . . . ?
C31 C32 C33 C34 58.1(9) . . . . ?
N28 N29 C34 C35 -59.4(7) . . . . ?
C30 N29 C34 C35 -178.2(6) . . . . ?
N28 N29 C34 C33 178.6(6) . . . . ?
C30 N29 C34 C33 59.9(8) . . . . ?
C32 C33 C34 N29 -59.6(8) . . . . ?
C32 C33 C34 C35 179.1(7) . . . . ?

_refine_diff_density_max         0.620
_refine_diff_density_min         -0.492
_refine_diff_density_rms         0.114

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2099755'
loop_
_audit_author_name
_audit_author_address
'Petra Bombicz'
;Centre for Structural Science, Research Centre for Natural Sciences
Hungary
;
_audit_update_record             
;
2021-07-27 deposited with the CCDC.	2021-08-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
trans-bis(4-chloro-N-(2,6-dimethylpiperidin-1-yl)-3-sulfamoylbenzamide)-copper(II)
_chemical_name_common            'clopamide copper(II)'
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H38 Cl2 Cu N6 O6 S2'
_chemical_formula_sum            'C28 H38 Cl2 Cu N6 O6 S2'
_chemical_formula_weight         753.20

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.8247(14)
_cell_length_b                   13.829(2)
_cell_length_c                   15.156(3)
_cell_angle_alpha                78.981(4)
_cell_angle_beta                 81.309(4)
_cell_angle_gamma                85.041(4)
_cell_volume                     1588.5(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    8318
_cell_measurement_theta_min      2.99
_cell_measurement_theta_max      25.41

_exptl_crystal_description       Chunk
_exptl_crystal_colour            Brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'Not measured'
_exptl_crystal_density_diffrn    1.575
_exptl_crystal_F_000             782
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    1.040
_shelx_estimated_absorpt_T_min   0.819
_shelx_estimated_absorpt_T_max   0.950
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.7778
_exptl_absorpt_correction_T_max  0.9414
_exptl_absorpt_process_details   
;
 T.Higashi, Numerical Absorption Correction, NUMABS, 2002
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      103(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'NORMAL-focus sealed tube'
_diffrn_radiation_monochromator  Graphite
_diffrn_radiation_detector       RX
_diffrn_measurement_device_type  R-AXIS-RAPID
_diffrn_measurement_method       dtprofit.ref
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            20566
_diffrn_reflns_av_unetI/netI     0.1661
_diffrn_reflns_av_R_equivalents  0.1852
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.984
_diffrn_reflns_theta_max         25.349
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5798
_reflns_number_gt                3000
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2006)'
_computing_publication_material  
;
MERCURY (Macrae et al., 2006); Platon (Spek,
 2009
;
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1284P)²+7.1679P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5798
_refine_ls_number_parameters     410
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2417
_refine_ls_R_factor_gt           0.1496
_refine_ls_wR_factor_ref         0.3567
_refine_ls_wR_factor_gt          0.3058
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_restrained_S_all      1.110
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
Cu1 Cu 0.76029(19) 0.50386(11) 0.24665(11) 0.0542(6) Uani 1 1 d . . . . .
Cl1 Cl 0.3186(5) -0.0582(2) 0.3906(3) 0.0691(11) Uani 1 1 d . . . . .
Cl2 Cl 1.2532(5) 1.0461(3) 0.1440(3) 0.0692(11) Uani 1 1 d . . . . .
S1 S 0.1695(4) 0.1375(3) 0.4775(3) 0.0582(10) Uani 1 1 d . . . . .
S2 S 1.2899(4) 0.8955(3) -0.0054(3) 0.0582(9) Uani 1 1 d . . . . .
O1 O 0.1570(11) 0.2321(7) 0.5032(6) 0.067(3) Uani 1 1 d . . . . .
O2 O 0.1595(11) 0.0521(7) 0.5466(6) 0.059(2) Uani 1 1 d . . . . .
O3 O 0.6255(10) 0.3928(6) 0.3018(6) 0.056(2) Uani 1 1 d . . . . .
O4 O 1.4570(11) 0.8756(6) 0.0235(7) 0.065(3) Uani 1 1 d . . . . .
O5 O 1.2365(13) 0.8359(8) -0.0598(6) 0.075(3) Uani 1 1 d . . . . .
O6 O 0.8925(10) 0.6156(6) 0.1899(6) 0.055(2) Uani 1 1 d . . . . .
N1 N 0.0223(14) 0.1315(8) 0.4160(8) 0.071(3) Uani 1 1 d . . . . .
H1NA H -0.0455 0.0792 0.4340 0.086 Uiso 1 1 d R U . . .
H1NB H -0.0086 0.1782 0.3694 0.086 Uiso 1 1 d R U . . .
N2 N 1.2827(14) 1.0048(9) -0.0602(8) 0.070(3) Uani 1 1 d . . . . .
H2NA H 1.1713 1.0213 -0.0702 0.084 Uiso 1 1 d R U . . .
H2NB H 1.3313 1.0475 -0.0339 0.084 Uiso 1 1 d R U . . .
N8 N 0.8731(13) 0.3013(8) 0.2514(7) 0.055(3) Uani 1 1 d . . . . .
N9 N 0.9354(12) 0.3984(7) 0.2096(7) 0.049(3) Uani 1 1 d . . . . .
N28 N 0.6657(13) 0.7048(8) 0.2629(7) 0.058(3) Uani 1 1 d . . . . .
N29 N 0.5887(12) 0.6085(8) 0.2903(8) 0.057(3) Uani 1 1 d . . . . .
C1 C 0.4684(16) 0.2142(10) 0.3838(9) 0.054(3) Uani 1 1 d . . . . .
H1 H 0.4286 0.2699 0.4110 0.065 Uiso 1 1 calc R U . . .
C2 C 0.3738(15) 0.1317(10) 0.4060(8) 0.048(3) Uani 1 1 d . . . . .
C3 C 0.4330(17) 0.0493(10) 0.3669(9) 0.055(3) Uani 1 1 d . . . . .
C4 C 0.5820(18) 0.0511(10) 0.3065(9) 0.061(4) Uani 1 1 d . . . . .
H4 H 0.6212 -0.0050 0.2798 0.073 Uiso 1 1 calc R U . . .
C5 C 0.6754(16) 0.1350(10) 0.2844(10) 0.060(4) Uani 1 1 d . . . . .
H5 H 0.7788 0.1359 0.2424 0.072 Uiso 1 1 calc R U . . .
C6 C 0.6198(16) 0.2186(10) 0.3231(9) 0.055(3) Uani 1 1 d . . . . .
C7 C 0.7156(16) 0.3104(9) 0.2899(9) 0.051(3) Uani 1 1 d . . . . .
C10 C 1.1123(15) 0.4089(11) 0.2342(10) 0.062(4) Uani 1 1 d . . . . .
H10 H 1.1512 0.4746 0.2007 0.075 Uiso 1 1 calc R U . . .
C11 C 1.2438(17) 0.3313(10) 0.2012(10) 0.065(4) Uani 1 1 d . . . . .
H11A H 1.3579 0.3400 0.2183 0.078 Uiso 1 1 calc R U . . .
H11B H 1.2077 0.2648 0.2316 0.078 Uiso 1 1 calc R U . . .
C12 C 1.2610(16) 0.3379(12) 0.0998(10) 0.066(4) Uani 1 1 d . . . . .
H12A H 1.3409 0.2835 0.0815 0.079 Uiso 1 1 calc R U . . .
H12B H 1.3101 0.4012 0.0688 0.079 Uiso 1 1 calc R U . . .
C13 C 1.0853(16) 0.3313(10) 0.0719(11) 0.067(4) Uani 1 1 d . . . . .
H13A H 1.0959 0.3434 0.0048 0.080 Uiso 1 1 calc R U . . .
H13B H 1.0462 0.2638 0.0947 0.080 Uiso 1 1 calc R U . . .
C14 C 0.9509(16) 0.4046(12) 0.1076(10) 0.067(4) Uani 1 1 d . . . . .
H14 H 0.9917 0.4716 0.0795 0.080 Uiso 1 1 calc R U . . .
C15 C 0.7738(16) 0.3999(10) 0.0774(9) 0.059(4) Uani 1 1 d . . . . .
H15A H 0.7236 0.3375 0.1072 0.089 Uiso 1 1 calc R U . . .
H15B H 0.7880 0.4043 0.0114 0.089 Uiso 1 1 calc R U . . .
H15C H 0.6965 0.4551 0.0942 0.089 Uiso 1 1 calc R U . . .
C16 C 1.0929(17) 0.4131(10) 0.3336(9) 0.064(4) Uani 1 1 d . . . . .
H16A H 1.0245 0.4733 0.3450 0.095 Uiso 1 1 calc R U . . .
H16B H 1.2077 0.4133 0.3520 0.095 Uiso 1 1 calc R U . . .
H16C H 1.0340 0.3553 0.3687 0.095 Uiso 1 1 calc R U . . .
C21 C 1.0328(16) 0.8028(9) 0.1129(9) 0.055(3) Uani 1 1 d . . . . .
H21 H 1.0423 0.7594 0.0706 0.066 Uiso 1 1 calc R U . . .
C22 C 1.1356(16) 0.8848(10) 0.0954(9) 0.054(3) Uani 1 1 d . . . . .
C23 C 1.1236(17) 0.9456(9) 0.1594(10) 0.057(3) Uani 1 1 d . . . . .
C24 C 1.0043(15) 0.9303(9) 0.2363(9) 0.051(3) Uani 1 1 d . . . . .
H24 H 0.9916 0.9745 0.2781 0.061 Uiso 1 1 calc R U . . .
C25 C 0.9034(16) 0.8506(10) 0.2524(9) 0.056(3) Uani 1 1 d . . . . .
H25 H 0.8220 0.8398 0.3060 0.067 Uiso 1 1 calc R U . . .
C26 C 0.9175(15) 0.7860(10) 0.1926(9) 0.054(3) Uani 1 1 d . . . . .
C27 C 0.8133(17) 0.6947(9) 0.2170(9) 0.051(3) Uani 1 1 d . . . . .
C30 C 0.4213(15) 0.6128(11) 0.2523(10) 0.062(4) Uani 1 1 d . . . . .
H30 H 0.3719 0.5466 0.2727 0.074 Uiso 1 1 calc R U . . .
C31 C 0.2910(19) 0.6882(12) 0.2886(12) 0.080(5) Uani 1 1 d . . . . .
H31A H 0.1803 0.6860 0.2651 0.096 Uiso 1 1 calc R U . . .
H31B H 0.3339 0.7549 0.2660 0.096 Uiso 1 1 calc R U . . .
C32 C 0.2583(17) 0.6705(11) 0.3916(10) 0.066(4) Uani 1 1 d . . . . .
H32A H 0.2001 0.6080 0.4146 0.079 Uiso 1 1 calc R U . . .
H32B H 0.1812 0.7249 0.4120 0.079 Uiso 1 1 calc R U . . .
C33 C 0.4289(17) 0.6649(10) 0.4295(10) 0.064(4) Uani 1 1 d . . . . .
H33A H 0.4803 0.7299 0.4125 0.076 Uiso 1 1 calc R U . . .
H33B H 0.4078 0.6480 0.4966 0.076 Uiso 1 1 calc R U . . .
C34 C 0.5537(16) 0.5873(11) 0.3925(10) 0.066(4) Uani 1 1 d . . . . .
H34 H 0.4991 0.5225 0.4113 0.079 Uiso 1 1 calc R U . . .
C35 C 0.7267(16) 0.5774(10) 0.4323(9) 0.061(4) Uani 1 1 d . . . . .
H35A H 0.7955 0.5190 0.4164 0.092 Uiso 1 1 calc R U . . .
H35B H 0.7026 0.5705 0.4985 0.092 Uiso 1 1 calc R U . . .
H35C H 0.7914 0.6364 0.4073 0.092 Uiso 1 1 calc R U . . .
C36 C 0.4562(18) 0.6313(11) 0.1491(10) 0.070(4) Uani 1 1 d . . . . .
H36A H 0.5050 0.6959 0.1270 0.105 Uiso 1 1 calc R U . . .
H36B H 0.3476 0.6303 0.1246 0.105 Uiso 1 1 calc R U . . .
H36C H 0.5386 0.5797 0.1291 0.105 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
Cu1 O3 1.921(8) . ?
Cu1 O6 1.923(8) . ?
Cu1 N9 2.013(10) . ?
Cu1 N29 2.024(10) . ?
Cl1 C3 1.752(13) . ?
Cl2 C23 1.750(13) . ?
S1 O2 1.420(9) . ?
S1 O1 1.426(9) . ?
S1 N1 1.604(11) . ?
S1 C2 1.796(12) . ?
S2 O5 1.399(10) . ?
S2 O4 1.429(9) . ?
S2 N2 1.579(12) . ?
S2 C22 1.790(13) . ?
O3 C7 1.316(14) . ?
O6 C27 1.313(14) . ?
N1 H1NA 0.9083 . ?
N1 H1NB 0.9088 . ?
N2 H2NA 0.9102 . ?
N2 H2NB 0.9094 . ?
N8 C7 1.288(15) . ?
N8 N9 1.462(14) . ?
N9 C10 1.513(14) . ?
N9 C14 1.518(17) . ?
N28 C27 1.267(16) . ?
N28 N29 1.470(14) . ?
N29 C30 1.500(15) . ?
N29 C34 1.508(17) . ?
C1 C2 1.374(16) . ?
C1 C6 1.384(18) . ?
C1 H1 0.9500 . ?
C2 C3 1.395(17) . ?
C3 C4 1.368(18) . ?
C4 C5 1.385(17) . ?
C4 H4 0.9500 . ?
C5 C6 1.401(18) . ?
C5 H5 0.9500 . ?
C6 C7 1.494(17) . ?
C10 C16 1.503(19) . ?
C10 C11 1.523(18) . ?
C10 H10 1.0000 . ?
C11 C12 1.51(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.514(18) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.510(18) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.534(17) . ?
C14 H14 1.0000 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C21 C26 1.388(17) . ?
C21 C22 1.407(17) . ?
C21 H21 0.9500 . ?
C22 C23 1.389(18) . ?
C23 C24 1.373(18) . ?
C24 C25 1.374(16) . ?
C24 H24 0.9500 . ?
C25 C26 1.375(17) . ?
C25 H25 0.9500 . ?
C26 C27 1.518(17) . ?
C30 C31 1.514(19) . ?
C30 C36 1.523(19) . ?
C30 H30 1.0000 . ?
C31 C32 1.52(2) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 C33 1.522(18) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.517(18) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 C35 1.549(17) . ?
C34 H34 1.0000 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?

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
O3 Cu1 O6 179.0(4) . . ?
O3 Cu1 N9 83.0(4) . . ?
O6 Cu1 N9 97.3(4) . . ?
O3 Cu1 N29 96.6(4) . . ?
O6 Cu1 N29 83.1(4) . . ?
N9 Cu1 N29 177.0(4) . . ?
O2 S1 O1 118.8(6) . . ?
O2 S1 N1 106.5(6) . . ?
O1 S1 N1 110.0(6) . . ?
O2 S1 C2 109.1(6) . . ?
O1 S1 C2 105.1(6) . . ?
N1 S1 C2 106.8(6) . . ?
O5 S2 O4 119.3(6) . . ?
O5 S2 N2 106.8(6) . . ?
O4 S2 N2 107.5(6) . . ?
O5 S2 C22 106.4(6) . . ?
O4 S2 C22 106.5(6) . . ?
N2 S2 C22 110.3(6) . . ?
C7 O3 Cu1 109.8(7) . . ?
C27 O6 Cu1 108.4(7) . . ?
S1 N1 H1NA 116.3 . . ?
S1 N1 H1NB 126.8 . . ?
H1NA N1 H1NB 116.5 . . ?
S2 N2 H2NA 107.7 . . ?
S2 N2 H2NB 112.9 . . ?
H2NA N2 H2NB 115.4 . . ?
C7 N8 N9 110.0(10) . . ?
N8 N9 C10 110.4(9) . . ?
N8 N9 C14 106.8(9) . . ?
C10 N9 C14 108.8(9) . . ?
N8 N9 Cu1 109.4(7) . . ?
C10 N9 Cu1 112.4(7) . . ?
C14 N9 Cu1 109.0(8) . . ?
C27 N28 N29 109.5(11) . . ?
N28 N29 C30 109.6(10) . . ?
N28 N29 C34 107.6(10) . . ?
C30 N29 C34 109.4(9) . . ?
N28 N29 Cu1 108.9(7) . . ?
C30 N29 Cu1 111.8(8) . . ?
C34 N29 Cu1 109.5(8) . . ?
C2 C1 C6 122.1(13) . . ?
C2 C1 H1 119.0 . . ?
C6 C1 H1 119.0 . . ?
C1 C2 C3 119.0(11) . . ?
C1 C2 S1 118.4(10) . . ?
C3 C2 S1 122.3(9) . . ?
C4 C3 C2 120.5(12) . . ?
C4 C3 Cl1 117.7(11) . . ?
C2 C3 Cl1 121.8(10) . . ?
C3 C4 C5 119.8(13) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C4 C5 C6 121.0(13) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 117.6(12) . . ?
C1 C6 C7 123.5(13) . . ?
C5 C6 C7 118.6(12) . . ?
N8 C7 O3 127.1(12) . . ?
N8 C7 C6 117.8(12) . . ?
O3 C7 C6 115.1(11) . . ?
C16 C10 N9 108.4(10) . . ?
C16 C10 C11 116.5(12) . . ?
N9 C10 C11 111.1(10) . . ?
C16 C10 H10 106.8 . . ?
N9 C10 H10 106.8 . . ?
C11 C10 H10 106.8 . . ?
C12 C11 C10 112.1(12) . . ?
C12 C11 H11A 109.2 . . ?
C10 C11 H11A 109.2 . . ?
C12 C11 H11B 109.2 . . ?
C10 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C11 C12 C13 109.8(11) . . ?
C11 C12 H12A 109.7 . . ?
C13 C12 H12A 109.7 . . ?
C11 C12 H12B 109.7 . . ?
C13 C12 H12B 109.7 . . ?
H12A C12 H12B 108.2 . . ?
C14 C13 C12 112.5(11) . . ?
C14 C13 H13A 109.1 . . ?
C12 C13 H13A 109.1 . . ?
C14 C13 H13B 109.1 . . ?
C12 C13 H13B 109.1 . . ?
H13A C13 H13B 107.8 . . ?
C13 C14 N9 113.4(11) . . ?
C13 C14 C15 112.6(11) . . ?
N9 C14 C15 111.4(10) . . ?
C13 C14 H14 106.3 . . ?
N9 C14 H14 106.3 . . ?
C15 C14 H14 106.3 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C10 C16 H16A 109.5 . . ?
C10 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C10 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C26 C21 C22 119.4(12) . . ?
C26 C21 H21 120.3 . . ?
C22 C21 H21 120.3 . . ?
C23 C22 C21 119.4(11) . . ?
C23 C22 S2 124.4(10) . . ?
C21 C22 S2 115.9(10) . . ?
C24 C23 C22 120.5(12) . . ?
C24 C23 Cl2 117.6(11) . . ?
C22 C23 Cl2 121.8(10) . . ?
C23 C24 C25 119.5(12) . . ?
C23 C24 H24 120.3 . . ?
C25 C24 H24 120.3 . . ?
C24 C25 C26 121.5(12) . . ?
C24 C25 H25 119.2 . . ?
C26 C25 H25 119.2 . . ?
C25 C26 C21 119.5(12) . . ?
C25 C26 C27 119.5(11) . . ?
C21 C26 C27 120.9(12) . . ?
N28 C27 O6 129.5(12) . . ?
N28 C27 C26 115.5(12) . . ?
O6 C27 C26 114.9(11) . . ?
N29 C30 C31 111.4(11) . . ?
N29 C30 C36 109.7(10) . . ?
C31 C30 C36 112.7(12) . . ?
N29 C30 H30 107.6 . . ?
C31 C30 H30 107.6 . . ?
C36 C30 H30 107.6 . . ?
C30 C31 C32 112.7(12) . . ?
C30 C31 H31A 109.1 . . ?
C32 C31 H31A 109.1 . . ?
C30 C31 H31B 109.1 . . ?
C32 C31 H31B 109.1 . . ?
H31A C31 H31B 107.8 . . ?
C31 C32 C33 110.0(12) . . ?
C31 C32 H32A 109.7 . . ?
C33 C32 H32A 109.7 . . ?
C31 C32 H32B 109.7 . . ?
C33 C32 H32B 109.7 . . ?
H32A C32 H32B 108.2 . . ?
C34 C33 C32 110.2(11) . . ?
C34 C33 H33A 109.6 . . ?
C32 C33 H33A 109.6 . . ?
C34 C33 H33B 109.6 . . ?
C32 C33 H33B 109.6 . . ?
H33A C33 H33B 108.1 . . ?
N29 C34 C33 112.0(11) . . ?
N29 C34 C35 109.8(10) . . ?
C33 C34 C35 111.4(12) . . ?
N29 C34 H34 107.8 . . ?
C33 C34 H34 107.8 . . ?
C35 C34 H34 107.8 . . ?
C34 C35 H35A 109.5 . . ?
C34 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C34 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C30 C36 H36A 109.5 . . ?
C30 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C30 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?

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
C7 N8 N9 C10 132.5(11) . . . . ?
C7 N8 N9 C14 -109.4(11) . . . . ?
C7 N8 N9 Cu1 8.4(12) . . . . ?
C27 N28 N29 C30 -119.9(11) . . . . ?
C27 N28 N29 C34 121.3(11) . . . . ?
C27 N28 N29 Cu1 2.7(12) . . . . ?
C6 C1 C2 C3 0.6(18) . . . . ?
C6 C1 C2 S1 -174.5(9) . . . . ?
O2 S1 C2 C1 -133.3(9) . . . . ?
O1 S1 C2 C1 -4.9(11) . . . . ?
N1 S1 C2 C1 111.9(10) . . . . ?
O2 S1 C2 C3 51.7(11) . . . . ?
O1 S1 C2 C3 -179.8(10) . . . . ?
N1 S1 C2 C3 -63.0(12) . . . . ?
C1 C2 C3 C4 -0.7(18) . . . . ?
S1 C2 C3 C4 174.2(10) . . . . ?
C1 C2 C3 Cl1 -179.2(9) . . . . ?
S1 C2 C3 Cl1 -4.3(15) . . . . ?
C2 C3 C4 C5 0(2) . . . . ?
Cl1 C3 C4 C5 179.0(10) . . . . ?
C3 C4 C5 C6 0(2) . . . . ?
C2 C1 C6 C5 -0.2(18) . . . . ?
C2 C1 C6 C7 173.3(11) . . . . ?
C4 C5 C6 C1 -0.1(19) . . . . ?
C4 C5 C6 C7 -173.9(12) . . . . ?
N9 N8 C7 O3 -8.1(18) . . . . ?
N9 N8 C7 C6 170.1(10) . . . . ?
Cu1 O3 C7 N8 3.0(16) . . . . ?
Cu1 O3 C7 C6 -175.2(8) . . . . ?
C1 C6 C7 N8 163.9(12) . . . . ?
C5 C6 C7 N8 -22.7(17) . . . . ?
C1 C6 C7 O3 -17.7(17) . . . . ?
C5 C6 C7 O3 155.7(11) . . . . ?
N8 N9 C10 C16 -68.8(12) . . . . ?
C14 N9 C10 C16 174.3(11) . . . . ?
Cu1 N9 C10 C16 53.5(12) . . . . ?
N8 N9 C10 C11 60.4(14) . . . . ?
C14 N9 C10 C11 -56.4(14) . . . . ?
Cu1 N9 C10 C11 -177.2(9) . . . . ?
C16 C10 C11 C12 -176.3(11) . . . . ?
N9 C10 C11 C12 58.9(15) . . . . ?
C10 C11 C12 C13 -55.2(16) . . . . ?
C11 C12 C13 C14 52.4(17) . . . . ?
C12 C13 C14 N9 -53.8(16) . . . . ?
C12 C13 C14 C15 178.5(12) . . . . ?
N8 N9 C14 C13 -64.5(12) . . . . ?
C10 N9 C14 C13 54.6(14) . . . . ?
Cu1 N9 C14 C13 177.5(9) . . . . ?
N8 N9 C14 C15 63.8(13) . . . . ?
C10 N9 C14 C15 -177.0(11) . . . . ?
Cu1 N9 C14 C15 -54.2(13) . . . . ?
C26 C21 C22 C23 2.0(19) . . . . ?
C26 C21 C22 S2 176.1(10) . . . . ?
O5 S2 C22 C23 -167.8(12) . . . . ?
O4 S2 C22 C23 63.9(13) . . . . ?
N2 S2 C22 C23 -52.5(13) . . . . ?
O5 S2 C22 C21 18.3(12) . . . . ?
O4 S2 C22 C21 -110.0(10) . . . . ?
N2 S2 C22 C21 133.7(10) . . . . ?
C21 C22 C23 C24 -4(2) . . . . ?
S2 C22 C23 C24 -178.1(10) . . . . ?
C21 C22 C23 Cl2 177.6(10) . . . . ?
S2 C22 C23 Cl2 4.0(17) . . . . ?
C22 C23 C24 C25 3.9(19) . . . . ?
Cl2 C23 C24 C25 -178.1(9) . . . . ?
C23 C24 C25 C26 -0.7(19) . . . . ?
C24 C25 C26 C21 -1.7(19) . . . . ?
C24 C25 C26 C27 175.2(11) . . . . ?
C22 C21 C26 C25 1.1(18) . . . . ?
C22 C21 C26 C27 -175.8(11) . . . . ?
N29 N28 C27 O6 3.7(18) . . . . ?
N29 N28 C27 C26 -173.5(9) . . . . ?
Cu1 O6 C27 N28 -8.3(16) . . . . ?
Cu1 O6 C27 C26 169.0(8) . . . . ?
C25 C26 C27 N28 33.9(17) . . . . ?
C21 C26 C27 N28 -149.2(12) . . . . ?
C25 C26 C27 O6 -143.8(12) . . . . ?
C21 C26 C27 O6 33.1(16) . . . . ?
N28 N29 C30 C31 -61.7(14) . . . . ?
C34 N29 C30 C31 56.0(15) . . . . ?
Cu1 N29 C30 C31 177.5(10) . . . . ?
N28 N29 C30 C36 63.9(13) . . . . ?
C34 N29 C30 C36 -178.4(11) . . . . ?
Cu1 N29 C30 C36 -57.0(13) . . . . ?
N29 C30 C31 C32 -55.3(16) . . . . ?
C36 C30 C31 C32 -179.2(12) . . . . ?
C30 C31 C32 C33 54.0(16) . . . . ?
C31 C32 C33 C34 -54.7(15) . . . . ?
N28 N29 C34 C33 60.4(12) . . . . ?
C30 N29 C34 C33 -58.6(14) . . . . ?
Cu1 N29 C34 C33 178.6(8) . . . . ?
N28 N29 C34 C35 -63.9(13) . . . . ?
C30 N29 C34 C35 177.1(11) . . . . ?
Cu1 N29 C34 C35 54.3(12) . . . . ?
C32 C33 C34 N29 58.4(14) . . . . ?
C32 C33 C34 C35 -178.1(12) . . . . ?

_refine_diff_density_max         1.197
_refine_diff_density_min         -0.645
_refine_diff_density_rms         0.128

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2099756'
loop_
_audit_author_name
_audit_author_address
'Petra Bombicz'
;Centre for Structural Science, Research Centre for Natural Sciences
Hungary
;
_audit_update_record             
;
2021-07-27 deposited with the CCDC.	2021-08-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
trans-bis(4-chloro-N-(2,6-dimethylpiperidin-1-yl)-3-sulfamoylbenzamide)-copper(II)
_chemical_name_common            'clopamide copper(II)'
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H38 Cl2 Cu N6 O6 S2'
_chemical_formula_sum            'C28 H38 Cl2 Cu N6 O6 S2'
_chemical_formula_weight         753.20

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   13.4600(10)
_cell_length_b                   15.2424(11)
_cell_length_c                   18.1855(16)
_cell_angle_alpha                114.627(6)
_cell_angle_beta                 93.362(8)
_cell_angle_gamma                90.021(6)
_cell_volume                     3384.5(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    35459
_cell_measurement_theta_min      2.99
_cell_measurement_theta_max      25.41

_exptl_crystal_description       chunk
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'Not measured'
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_F_000             1564
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.976
_shelx_estimated_absorpt_T_min   0.909
_shelx_estimated_absorpt_T_max   0.909
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.7778
_exptl_absorpt_correction_T_max  0.9414
_exptl_absorpt_process_details   
;
 T.Higashi, Numerical Absorption Correction, NUMABS, 2002
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'NORMAL-focus sealed tube'
_diffrn_radiation_monochromator  Graphite
_diffrn_radiation_detector       RX
_diffrn_measurement_device_type  R-AXIS-RAPID
_diffrn_measurement_method       dtprofit.ref
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            51524
_diffrn_reflns_av_unetI/netI     0.1110
_diffrn_reflns_av_R_equivalents  0.1301
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.033
_diffrn_reflns_theta_max         25.308
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             12256
_reflns_number_gt                7883
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2006)'
_computing_publication_material  
;
MERCURY (Macrae et al., 2006); Platon (Spek,
 2009
;
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0373P)²+5.5982P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         12256
_refine_ls_number_parameters     822
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1375
_refine_ls_R_factor_gt           0.0777
_refine_ls_wR_factor_ref         0.1368
_refine_ls_wR_factor_gt          0.1200
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
Cu1 Cu 0.04547(5) 1.00016(5) 0.71724(4) 0.03043(19) Uani 1 1 d . . . . .
Cl1 Cl 0.19105(13) 0.63399(12) 0.24088(9) 0.0504(5) Uani 1 1 d . . . . .
Cl2 Cl -0.12613(12) 1.36957(11) 1.18279(9) 0.0401(4) Uani 1 1 d . . . . .
S1 S 0.04332(13) 0.58484(11) 0.35781(9) 0.0396(4) Uani 1 1 d . . . . .
S2 S 0.04190(11) 1.41104(10) 1.07581(9) 0.0314(4) Uani 1 1 d . . . . .
O1 O 0.0061(4) 0.5853(3) 0.4297(2) 0.0535(13) Uani 1 1 d . . . . .
O2 O -0.0246(3) 0.5822(3) 0.2929(2) 0.0419(11) Uani 1 1 d . . . . .
O3 O 0.0700(3) 0.9010(3) 0.6162(2) 0.0357(10) Uani 1 1 d . . . . .
O4 O 0.0864(3) 1.4119(3) 1.0064(2) 0.0342(10) Uani 1 1 d . . . . .
O5 O 0.1030(3) 1.4033(3) 1.1392(2) 0.0364(10) Uani 1 1 d . . . . .
O6 O 0.0158(3) 1.1003(3) 0.8150(2) 0.0368(10) Uani 1 1 d . . . . .
N1 N 0.1137(4) 0.4949(3) 0.3206(3) 0.0453(14) Uani 1 1 d . . . . .
H1NB H 0.1624 0.4901 0.3554 0.054 Uiso 1 1 d R U . . .
H1NA H 0.1296 0.4713 0.2679 0.054 Uiso 1 1 d R U . . .
N2 N -0.0204(3) 1.5060(3) 1.1138(3) 0.0370(13) Uani 1 1 d . . . . .
H2NB H -0.0447 1.5343 1.0817 0.044 Uiso 1 1 d R U . . .
H2NA H -0.0337 1.5345 1.1669 0.044 Uiso 1 1 d R U . . .
N8 N 0.2011(3) 0.9981(3) 0.6152(3) 0.0311(12) Uani 1 1 d . . . . .
N9 N 0.1704(3) 1.0629(3) 0.6958(3) 0.0280(11) Uani 1 1 d . . . . .
N28 N -0.1167(4) 1.0030(3) 0.8138(3) 0.0405(13) Uani 1 1 d . . . . .
N29 N -0.0767(4) 0.9342(3) 0.7375(3) 0.0337(12) Uani 1 1 d . . . . .
C1 C 0.1084(4) 0.7612(4) 0.4688(3) 0.0323(14) Uani 1 1 d . . . . .
H1 H 0.0667 0.7476 0.5033 0.039 Uiso 1 1 calc R U . . .
C2 C 0.1163(4) 0.6935(4) 0.3908(3) 0.0318(14) Uani 1 1 d . . . . .
C3 C 0.1777(4) 0.7137(4) 0.3406(3) 0.0338(15) Uani 1 1 d . . . . .
C4 C 0.2314(4) 0.8000(4) 0.3703(4) 0.0385(15) Uani 1 1 d . . . . .
H4 H 0.2750 0.8131 0.3366 0.046 Uiso 1 1 calc R U . . .
C5 C 0.2220(4) 0.8668(4) 0.4480(4) 0.0374(15) Uani 1 1 d . . . . .
H5 H 0.2588 0.9262 0.4675 0.045 Uiso 1 1 calc R U . . .
C6 C 0.1604(4) 0.8497(4) 0.4984(3) 0.0288(14) Uani 1 1 d . . . . .
C7 C 0.1426(4) 0.9209(4) 0.5825(3) 0.0288(14) Uani 1 1 d . . . . .
C10 C 0.1548(4) 1.1593(4) 0.6905(4) 0.0351(15) Uani 1 1 d . . . . .
H10 H 0.2153 1.1737 0.6675 0.042 Uiso 1 1 calc R U . . .
C11 C 0.1449(5) 1.2412(4) 0.7721(4) 0.0410(16) Uani 1 1 d . . . . .
H11A H 0.0821 1.2317 0.7940 0.049 Uiso 1 1 calc R U . . .
H11B H 0.1406 1.3024 0.7655 0.049 Uiso 1 1 calc R U . . .
C12 C 0.2315(5) 1.2495(4) 0.8327(4) 0.0448(17) Uani 1 1 d . . . . .
H12C H 0.2927 1.2708 0.8165 0.054 Uiso 1 1 calc R U . . .
H12D H 0.2170 1.2982 0.8871 0.054 Uiso 1 1 calc R U . . .
C13 C 0.2476(5) 1.1534(4) 0.8357(4) 0.0445(17) Uani 1 1 d . . . . .
H13A H 0.1901 1.1377 0.8600 0.053 Uiso 1 1 calc R U . . .
H13B H 0.3077 1.1586 0.8715 0.053 Uiso 1 1 calc R U . . .
C14 C 0.2599(4) 1.0722(4) 0.7539(3) 0.0342(15) Uani 1 1 d . . . . .
H14 H 0.3192 1.0891 0.7312 0.041 Uiso 1 1 calc R U . . .
C15 C 0.2795(5) 0.9760(4) 0.7576(4) 0.0504(19) Uani 1 1 d . . . . .
H15D H 0.2250 0.9595 0.7833 0.076 Uiso 1 1 calc R U . . .
H15E H 0.3423 0.9807 0.7893 0.076 Uiso 1 1 calc R U . . .
H15F H 0.2839 0.9258 0.7025 0.076 Uiso 1 1 calc R U . . .
C16 C 0.0672(5) 1.1498(4) 0.6316(4) 0.0458(17) Uani 1 1 d . . . . .
H16D H 0.0060 1.1387 0.6536 0.069 Uiso 1 1 calc R U . . .
H16E H 0.0767 1.0953 0.5797 0.069 Uiso 1 1 calc R U . . .
H16F H 0.0618 1.2093 0.6235 0.069 Uiso 1 1 calc R U . . .
C21 C -0.0299(4) 1.2401(4) 0.9592(3) 0.0299(14) Uani 1 1 d . . . . .
H21 H 0.0183 1.2512 0.9277 0.036 Uiso 1 1 calc R U . . .
C22 C -0.0414(4) 1.3092(4) 1.0370(3) 0.0281(13) Uani 1 1 d . . . . .
C23 C -0.1133(4) 1.2914(4) 1.0819(3) 0.0310(14) Uani 1 1 d . . . . .
C24 C -0.1731(4) 1.2083(4) 1.0484(4) 0.0353(15) Uani 1 1 d . . . . .
H24 H -0.2231 1.1978 1.0789 0.042 Uiso 1 1 calc R U . . .
C25 C -0.1598(4) 1.1408(4) 0.9706(3) 0.0347(15) Uani 1 1 d . . . . .
H25 H -0.2010 1.0840 0.9475 0.042 Uiso 1 1 calc R U . . .
C26 C -0.0871(4) 1.1554(4) 0.9262(3) 0.0296(14) Uani 1 1 d . . . . .
C27 C -0.0616(5) 1.0805(4) 0.8451(3) 0.0343(15) Uani 1 1 d . . . . .
C30 C -0.0548(5) 0.8463(4) 0.7532(4) 0.0443(17) Uani 1 1 d . . . . .
H30 H -0.1156 0.8305 0.7748 0.053 Uiso 1 1 calc R U . . .
C31 C -0.0343(5) 0.7600(4) 0.6776(4) 0.0499(18) Uani 1 1 d . . . . .
H31A H -0.0238 0.7037 0.6908 0.060 Uiso 1 1 calc R U . . .
H31B H 0.0277 0.7722 0.6563 0.060 Uiso 1 1 calc R U . . .
C32 C -0.1188(5) 0.7363(5) 0.6128(4) 0.055(2) Uani 1 1 d . . . . .
H32A H -0.0987 0.6842 0.5618 0.065 Uiso 1 1 calc R U . . .
H32B H -0.1778 0.7127 0.6300 0.065 Uiso 1 1 calc R U . . .
C33 C -0.1460(5) 0.8242(4) 0.5977(4) 0.0470(17) Uani 1 1 d . . . . .
H33A H -0.0922 0.8389 0.5694 0.056 Uiso 1 1 calc R U . . .
H33B H -0.2076 0.8093 0.5618 0.056 Uiso 1 1 calc R U . . .
C34 C -0.1617(5) 0.9114(4) 0.6746(4) 0.0419(16) Uani 1 1 d . . . . .
H34 H -0.2220 0.8978 0.6981 0.050 Uiso 1 1 calc R U . . .
C35 C -0.1820(5) 0.9989(5) 0.6585(4) 0.0465(17) Uani 1 1 d . . . . .
H35A H -0.1932 1.0541 0.7096 0.070 Uiso 1 1 calc R U . . .
H35B H -0.2413 0.9863 0.6212 0.070 Uiso 1 1 calc R U . . .
H35C H -0.1247 1.0132 0.6341 0.070 Uiso 1 1 calc R U . . .
C36 C 0.0295(6) 0.8687(5) 0.8185(4) 0.064(2) Uani 1 1 d . . . . .
H36A H 0.0911 0.8826 0.7986 0.095 Uiso 1 1 calc R U . . .
H36B H 0.0388 0.8130 0.8316 0.095 Uiso 1 1 calc R U . . .
H36C H 0.0130 0.9250 0.8672 0.095 Uiso 1 1 calc R U . . .
Cu2 Cu 0.5000 0.5000 1.0000 0.0230(2) Uani 1 2 d S . P . .
Cl1' Cl 0.55451(13) -0.06122(10) 0.62706(10) 0.0494(5) Uani 1 1 d . . . . .
S1' S 0.46098(12) 0.13464(11) 0.61464(9) 0.0355(4) Uani 1 1 d . . . . .
O1' O 0.4058(3) 0.2205(3) 0.6391(2) 0.0408(11) Uani 1 1 d . . . . .
O2' O 0.5446(3) 0.1244(3) 0.5663(2) 0.0386(10) Uani 1 1 d . . . . .
O3' O 0.5126(3) 0.3854(2) 0.9070(2) 0.0285(9) Uani 1 1 d . . . . .
N1' N 0.3870(4) 0.0453(3) 0.5661(3) 0.0407(13) Uani 1 1 d . . . . .
H1NC H 0.4206 -0.0090 0.5386 0.049 Uiso 1 1 d R U . . .
H1ND H 0.3253 0.0361 0.5797 0.049 Uiso 1 1 d R U . . .
N8' N 0.5476(3) 0.3132(3) 0.9944(3) 0.0249(10) Uani 1 1 d . . . . .
N9' N 0.5358(3) 0.4117(3) 1.0582(2) 0.0234(10) Uani 1 1 d . . . . .
C1' C 0.5060(4) 0.2139(4) 0.7766(3) 0.0269(13) Uani 1 1 d . . . . .
H1' H 0.4772 0.2695 0.7739 0.032 Uiso 1 1 calc R U . . .
C2' C 0.5089(4) 0.1303(4) 0.7060(3) 0.0254(13) Uani 1 1 d . . . . .
C3' C 0.5517(4) 0.0489(4) 0.7111(4) 0.0355(15) Uani 1 1 d . . . . .
C4' C 0.5917(4) 0.0541(4) 0.7843(4) 0.0351(15) Uani 1 1 d . . . . .
H4' H 0.6210 -0.0011 0.7873 0.042 Uiso 1 1 calc R U . . .
C5' C 0.5895(4) 0.1392(4) 0.8536(3) 0.0336(14) Uani 1 1 d . . . . .
H5' H 0.6197 0.1427 0.9033 0.040 Uiso 1 1 calc R U . . .
C6' C 0.5436(4) 0.2195(4) 0.8510(3) 0.0243(13) Uani 1 1 d . . . . .
C7' C 0.5346(4) 0.3122(4) 0.9234(3) 0.0240(12) Uani 1 1 d . . . . .
C10' C 0.6356(4) 0.4359(4) 1.1056(3) 0.0320(14) Uani 1 1 d . . . . .
H10' H 0.6548 0.3791 1.1170 0.038 Uiso 1 1 calc R U . . .
C11' C 0.6316(5) 0.5213(4) 1.1853(4) 0.0444(17) Uani 1 1 d . . . . .
H11C H 0.6194 0.5797 1.1755 0.053 Uiso 1 1 calc R U . . .
H11D H 0.6969 0.5305 1.2159 0.053 Uiso 1 1 calc R U . . .
C12' C 0.5510(6) 0.5107(5) 1.2363(4) 0.055(2) Uani 1 1 d . . . . .
H12A H 0.5673 0.4578 1.2528 0.066 Uiso 1 1 calc R U . . .
H12B H 0.5471 0.5712 1.2859 0.066 Uiso 1 1 calc R U . . .
C13' C 0.4525(5) 0.4885(4) 1.1875(4) 0.0412(16) Uani 1 1 d . . . . .
H13C H 0.4010 0.4777 1.2197 0.049 Uiso 1 1 calc R U . . .
H13D H 0.4334 0.5450 1.1768 0.049 Uiso 1 1 calc R U . . .
C14' C 0.4552(4) 0.4014(4) 1.1084(3) 0.0313(14) Uani 1 1 d . . . . .
H14' H 0.4713 0.3449 1.1209 0.038 Uiso 1 1 calc R U . . .
C15' C 0.3559(4) 0.3790(4) 1.0596(4) 0.0421(16) Uani 1 1 d . . . . .
H15A H 0.3383 0.4330 1.0458 0.063 Uiso 1 1 calc R U . . .
H15B H 0.3045 0.3695 1.0918 0.063 Uiso 1 1 calc R U . . .
H15C H 0.3606 0.3201 1.0098 0.063 Uiso 1 1 calc R U . . .
C16' C 0.7134(4) 0.4498(4) 1.0546(4) 0.0393(16) Uani 1 1 d . . . . .
H16A H 0.6966 0.5052 1.0426 0.059 Uiso 1 1 calc R U . . .
H16B H 0.7153 0.3917 1.0038 0.059 Uiso 1 1 calc R U . . .
H16C H 0.7787 0.4617 1.0844 0.059 Uiso 1 1 calc R U . . .
Cu3 Cu 0.5000 0.5000 0.5000 0.0308(3) Uani 1 2 d S . P . .
Cl2' Cl 0.68659(12) 0.91347(11) 0.97085(9) 0.0418(4) Uani 1 1 d . . . . .
S2' S 0.45941(11) 0.86282(9) 0.88202(8) 0.0267(3) Uani 1 1 d . . . . .
O4' O 0.3770(3) 0.8063(3) 0.8314(2) 0.0345(10) Uani 1 1 d . . . . .
O5' O 0.4708(3) 0.9616(2) 0.8947(2) 0.0307(9) Uani 1 1 d . . . . .
O6' O 0.5214(3) 0.5944(3) 0.6065(2) 0.0333(10) Uani 1 1 d . . . . .
N2' N 0.4543(3) 0.8619(3) 0.9686(3) 0.0297(11) Uani 1 1 d . . . . .
H2ND H 0.4479 0.8044 0.9707 0.036 Uiso 1 1 d R U . . .
H2NC H 0.4933 0.9077 1.0098 0.036 Uiso 1 1 d R U . . .
N28' N 0.6837(4) 0.5446(3) 0.5995(3) 0.0336(12) Uani 1 1 d . . . . .
N29' N 0.6503(4) 0.4766(3) 0.5157(3) 0.0368(12) Uani 1 1 d . . . . .
C21' C 0.5541(4) 0.7288(4) 0.7590(3) 0.0257(13) Uani 1 1 d . . . . .
H21' H 0.4895 0.7149 0.7323 0.031 Uiso 1 1 calc R U . . .
C22' C 0.5674(4) 0.8022(4) 0.8367(3) 0.0224(12) Uani 1 1 d . . . . .
C23' C 0.6631(4) 0.8212(4) 0.8744(3) 0.0308(14) Uani 1 1 d . . . . .
C24' C 0.7414(4) 0.7657(4) 0.8372(3) 0.0322(14) Uani 1 1 d . . . . .
H24' H 0.8055 0.7767 0.8648 0.039 Uiso 1 1 calc R U . . .
C25' C 0.7265(4) 0.6936(4) 0.7594(3) 0.0344(15) Uani 1 1 d . . . . .
H25' H 0.7811 0.6564 0.7332 0.041 Uiso 1 1 calc R U . . .
C26' C 0.6339(4) 0.6752(4) 0.7196(3) 0.0277(13) Uani 1 1 d . . . . .
C27' C 0.6117(5) 0.5983(4) 0.6350(3) 0.0285(14) Uani 1 1 d . . . . .
C30' C 0.7211(5) 0.4971(5) 0.4626(4) 0.0531(19) Uani 1 1 d . . . . .
H30' H 0.7900 0.5044 0.4885 0.064 Uiso 1 1 calc R U . . .
C31' C 0.7199(6) 0.4166(5) 0.3793(4) 0.068(2) Uani 1 1 d . . . . .
H31C H 0.7711 0.4308 0.3486 0.081 Uiso 1 1 calc R U . . .
H31D H 0.6543 0.4137 0.3507 0.081 Uiso 1 1 calc R U . . .
C32' C 0.7395(6) 0.3189(6) 0.3801(5) 0.077(3) Uani 1 1 d . . . . .
H32C H 0.7333 0.2680 0.3241 0.092 Uiso 1 1 calc R U . . .
H32D H 0.8081 0.3185 0.4029 0.092 Uiso 1 1 calc R U . . .
C33' C 0.6654(6) 0.2982(5) 0.4310(5) 0.069(2) Uani 1 1 d . . . . .
H33C H 0.5975 0.2926 0.4052 0.083 Uiso 1 1 calc R U . . .
H33D H 0.6806 0.2357 0.4332 0.083 Uiso 1 1 calc R U . . .
C34' C 0.6686(5) 0.3755(4) 0.5149(4) 0.053(2) Uani 1 1 d . . . . .
H34' H 0.7373 0.3775 0.5397 0.064 Uiso 1 1 calc R U . . .
C35' C 0.5989(6) 0.3555(5) 0.5665(5) 0.066(2) Uani 1 1 d . . . . .
H35D H 0.5302 0.3564 0.5457 0.099 Uiso 1 1 calc R U . . .
H35E H 0.6084 0.4050 0.6222 0.099 Uiso 1 1 calc R U . . .
H35F H 0.6119 0.2918 0.5657 0.099 Uiso 1 1 calc R U . . .
C36' C 0.6931(6) 0.5924(5) 0.4612(4) 0.062(2) Uani 1 1 d . . . . .
H36D H 0.6285 0.5850 0.4312 0.093 Uiso 1 1 calc R U . . .
H36E H 0.7439 0.6129 0.4347 0.093 Uiso 1 1 calc R U . . .
H36F H 0.6889 0.6412 0.5169 0.093 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
Cu1 O6 1.863(4) . ?
Cu1 O3 1.878(4) . ?
Cu1 N29 2.057(5) . ?
Cu1 N9 2.070(5) . ?
Cl1 C3 1.732(6) . ?
Cl2 C23 1.742(6) . ?
S1 O1 1.424(4) . ?
S1 O2 1.437(4) . ?
S1 N1 1.593(5) . ?
S1 C2 1.780(6) . ?
S2 O5 1.423(4) . ?
S2 O4 1.433(4) . ?
S2 N2 1.584(4) . ?
S2 C22 1.777(6) . ?
O3 C7 1.283(6) . ?
O6 C27 1.297(7) . ?
N1 H1NB 0.9086 . ?
N1 H1NA 0.9108 . ?
N2 H2NB 0.9065 . ?
N2 H2NA 0.9076 . ?
N8 C7 1.312(7) . ?
N8 N9 1.468(6) . ?
N9 C14 1.521(7) . ?
N9 C10 1.526(7) . ?
N28 C27 1.288(7) . ?
N28 N29 1.480(6) . ?
N29 C34 1.500(7) . ?
N29 C30 1.507(7) . ?
C1 C2 1.374(7) . ?
C1 C6 1.395(7) . ?
C1 H1 0.9500 . ?
C2 C3 1.390(8) . ?
C3 C4 1.381(8) . ?
C4 C5 1.368(8) . ?
C4 H4 0.9500 . ?
C5 C6 1.373(8) . ?
C5 H5 0.9500 . ?
C6 C7 1.495(7) . ?
C10 C11 1.502(8) . ?
C10 C16 1.510(8) . ?
C10 H10 1.0000 . ?
C11 C12 1.525(9) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.502(8) . ?
C12 H12C 0.9900 . ?
C12 H12D 0.9900 . ?
C13 C14 1.506(8) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.518(8) . ?
C14 H14 1.0000 . ?
C15 H15D 0.9800 . ?
C15 H15E 0.9800 . ?
C15 H15F 0.9800 . ?
C16 H16D 0.9800 . ?
C16 H16E 0.9800 . ?
C16 H16F 0.9800 . ?
C21 C26 1.385(7) . ?
C21 C22 1.386(7) . ?
C21 H21 0.9500 . ?
C22 C23 1.397(7) . ?
C23 C24 1.387(8) . ?
C24 C25 1.382(8) . ?
C24 H24 0.9500 . ?
C25 C26 1.380(8) . ?
C25 H25 0.9500 . ?
C26 C27 1.501(7) . ?
C30 C31 1.494(8) . ?
C30 C36 1.522(9) . ?
C30 H30 1.0000 . ?
C31 C32 1.518(9) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 C33 1.515(9) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.501(8) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 C35 1.502(8) . ?
C34 H34 1.0000 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
Cu2 O3' 1.874(3) 2_667 ?
Cu2 O3' 1.874(3) . ?
Cu2 N9' 2.072(4) . ?
Cu2 N9' 2.072(4) 2_667 ?
Cl1' C3' 1.739(6) . ?
S1' O1' 1.419(4) . ?
S1' O2' 1.437(4) . ?
S1' N1' 1.587(5) . ?
S1' C2' 1.774(6) . ?
O3' C7' 1.300(6) . ?
N1' H1NC 0.9063 . ?
N1' H1ND 0.9088 . ?
N8' C7' 1.286(6) . ?
N8' N9' 1.482(5) . ?
N9' C14' 1.506(7) . ?
N9' C10' 1.511(7) . ?
C1' C2' 1.384(7) . ?
C1' C6' 1.386(7) . ?
C1' H1' 0.9500 . ?
C2' C3' 1.404(8) . ?
C3' C4' 1.377(8) . ?
C4' C5' 1.382(7) . ?
C4' H4' 0.9500 . ?
C5' C6' 1.388(7) . ?
C5' H5' 0.9500 . ?
C6' C7' 1.488(7) . ?
C10' C11' 1.495(8) . ?
C10' C16' 1.509(8) . ?
C10' H10' 1.0000 . ?
C11' C12' 1.518(9) . ?
C11' H11C 0.9900 . ?
C11' H11D 0.9900 . ?
C12' C13' 1.507(9) . ?
C12' H12A 0.9900 . ?
C12' H12B 0.9900 . ?
C13' C14' 1.499(7) . ?
C13' H13C 0.9900 . ?
C13' H13D 0.9900 . ?
C14' C15' 1.516(8) . ?
C14' H14' 1.0000 . ?
C15' H15A 0.9800 . ?
C15' H15B 0.9800 . ?
C15' H15C 0.9800 . ?
C16' H16A 0.9800 . ?
C16' H16B 0.9800 . ?
C16' H16C 0.9800 . ?
Cu3 O6' 1.875(4) . ?
Cu3 O6' 1.875(4) 2_666 ?
Cu3 N29' 2.078(5) 2_666 ?
Cu3 N29' 2.078(5) . ?
Cl2' C23' 1.742(5) . ?
S2' O4' 1.429(4) . ?
S2' O5' 1.433(4) . ?
S2' N2' 1.586(4) . ?
S2' C22' 1.776(5) . ?
O6' C27' 1.284(7) . ?
N2' H2ND 0.8974 . ?
N2' H2NC 0.9180 . ?
N28' C27' 1.288(7) . ?
N28' N29' 1.484(6) . ?
N29' C30' 1.515(8) . ?
N29' C34' 1.556(8) . ?
C21' C22' 1.390(7) . ?
C21' C26' 1.391(7) . ?
C21' H21' 0.9500 . ?
C22' C23' 1.395(7) . ?
C23' C24' 1.375(8) . ?
C24' C25' 1.387(7) . ?
C24' H24' 0.9500 . ?
C25' C26' 1.371(8) . ?
C25' H25' 0.9500 . ?
C26' C27' 1.508(7) . ?
C30' C31' 1.499(9) . ?
C30' C36' 1.511(9) . ?
C30' H30' 1.0000 . ?
C31' C32' 1.519(10) . ?
C31' H31C 0.9900 . ?
C31' H31D 0.9900 . ?
C32' C33' 1.518(11) . ?
C32' H32C 0.9900 . ?
C32' H32D 0.9900 . ?
C33' C34' 1.487(9) . ?
C33' H33C 0.9900 . ?
C33' H33D 0.9900 . ?
C34' C35' 1.481(10) . ?
C34' H34' 1.0000 . ?
C35' H35D 0.9800 . ?
C35' H35E 0.9800 . ?
C35' H35F 0.9800 . ?
C36' H36D 0.9800 . ?
C36' H36E 0.9800 . ?
C36' H36F 0.9800 . ?

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
O6 Cu1 O3 177.11(19) . . ?
O6 Cu1 N29 83.00(17) . . ?
O3 Cu1 N29 96.28(17) . . ?
O6 Cu1 N9 98.23(17) . . ?
O3 Cu1 N9 82.55(17) . . ?
N29 Cu1 N9 178.39(17) . . ?
O1 S1 O2 120.1(3) . . ?
O1 S1 N1 108.3(3) . . ?
O2 S1 N1 107.0(2) . . ?
O1 S1 C2 105.1(3) . . ?
O2 S1 C2 106.9(3) . . ?
N1 S1 C2 109.2(3) . . ?
O5 S2 O4 119.8(2) . . ?
O5 S2 N2 108.2(2) . . ?
O4 S2 N2 107.6(2) . . ?
O5 S2 C22 106.8(3) . . ?
O4 S2 C22 105.3(2) . . ?
N2 S2 C22 108.9(3) . . ?
C7 O3 Cu1 113.3(3) . . ?
C27 O6 Cu1 112.6(3) . . ?
S1 N1 H1NB 115.5 . . ?
S1 N1 H1NA 121.5 . . ?
H1NB N1 H1NA 114.8 . . ?
S2 N2 H2NB 119.6 . . ?
S2 N2 H2NA 123.5 . . ?
H2NB N2 H2NA 116.9 . . ?
C7 N8 N9 111.0(4) . . ?
N8 N9 C14 105.3(4) . . ?
N8 N9 C10 104.4(4) . . ?
C14 N9 C10 109.3(4) . . ?
N8 N9 Cu1 107.2(3) . . ?
C14 N9 Cu1 113.9(3) . . ?
C10 N9 Cu1 115.7(3) . . ?
C27 N28 N29 110.1(5) . . ?
N28 N29 C34 105.1(4) . . ?
N28 N29 C30 103.8(4) . . ?
C34 N29 C30 109.6(4) . . ?
N28 N29 Cu1 107.3(3) . . ?
C34 N29 Cu1 114.9(4) . . ?
C30 N29 Cu1 115.0(4) . . ?
C2 C1 C6 121.4(6) . . ?
C2 C1 H1 119.3 . . ?
C6 C1 H1 119.3 . . ?
C1 C2 C3 119.1(5) . . ?
C1 C2 S1 117.8(5) . . ?
C3 C2 S1 123.0(4) . . ?
C4 C3 C2 119.8(5) . . ?
C4 C3 Cl1 117.6(5) . . ?
C2 C3 Cl1 122.7(4) . . ?
C5 C4 C3 120.2(6) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 121.3(6) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C5 C6 C1 118.2(5) . . ?
C5 C6 C7 124.3(5) . . ?
C1 C6 C7 117.5(5) . . ?
O3 C7 N8 125.7(5) . . ?
O3 C7 C6 116.4(5) . . ?
N8 C7 C6 117.9(5) . . ?
C11 C10 C16 112.5(5) . . ?
C11 C10 N9 112.5(5) . . ?
C16 C10 N9 109.5(4) . . ?
C11 C10 H10 107.3 . . ?
C16 C10 H10 107.3 . . ?
N9 C10 H10 107.3 . . ?
C10 C11 C12 112.9(5) . . ?
C10 C11 H11A 109.0 . . ?
C12 C11 H11A 109.0 . . ?
C10 C11 H11B 109.0 . . ?
C12 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
C13 C12 C11 109.9(5) . . ?
C13 C12 H12C 109.7 . . ?
C11 C12 H12C 109.7 . . ?
C13 C12 H12D 109.7 . . ?
C11 C12 H12D 109.7 . . ?
H12C C12 H12D 108.2 . . ?
C12 C13 C14 113.6(5) . . ?
C12 C13 H13A 108.8 . . ?
C14 C13 H13A 108.8 . . ?
C12 C13 H13B 108.8 . . ?
C14 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
C13 C14 C15 113.4(5) . . ?
C13 C14 N9 110.9(5) . . ?
C15 C14 N9 110.3(4) . . ?
C13 C14 H14 107.3 . . ?
C15 C14 H14 107.3 . . ?
N9 C14 H14 107.3 . . ?
C14 C15 H15D 109.5 . . ?
C14 C15 H15E 109.5 . . ?
H15D C15 H15E 109.5 . . ?
C14 C15 H15F 109.5 . . ?
H15D C15 H15F 109.5 . . ?
H15E C15 H15F 109.5 . . ?
C10 C16 H16D 109.5 . . ?
C10 C16 H16E 109.5 . . ?
H16D C16 H16E 109.5 . . ?
C10 C16 H16F 109.5 . . ?
H16D C16 H16F 109.5 . . ?
H16E C16 H16F 109.5 . . ?
C26 C21 C22 121.6(5) . . ?
C26 C21 H21 119.2 . . ?
C22 C21 H21 119.2 . . ?
C21 C22 C23 118.0(5) . . ?
C21 C22 S2 117.8(4) . . ?
C23 C22 S2 124.1(4) . . ?
C24 C23 C22 120.8(5) . . ?
C24 C23 Cl2 118.1(4) . . ?
C22 C23 Cl2 121.1(4) . . ?
C25 C24 C23 119.8(5) . . ?
C25 C24 H24 120.1 . . ?
C23 C24 H24 120.1 . . ?
C26 C25 C24 120.3(5) . . ?
C26 C25 H25 119.8 . . ?
C24 C25 H25 119.8 . . ?
C25 C26 C21 119.4(5) . . ?
C25 C26 C27 122.9(5) . . ?
C21 C26 C27 117.6(5) . . ?
N28 C27 O6 126.9(5) . . ?
N28 C27 C26 117.3(5) . . ?
O6 C27 C26 115.8(5) . . ?
C31 C30 N29 112.4(5) . . ?
C31 C30 C36 111.9(6) . . ?
N29 C30 C36 110.4(5) . . ?
C31 C30 H30 107.3 . . ?
N29 C30 H30 107.3 . . ?
C36 C30 H30 107.3 . . ?
C30 C31 C32 112.2(6) . . ?
C30 C31 H31A 109.2 . . ?
C32 C31 H31A 109.2 . . ?
C30 C31 H31B 109.2 . . ?
C32 C31 H31B 109.2 . . ?
H31A C31 H31B 107.9 . . ?
C33 C32 C31 111.1(5) . . ?
C33 C32 H32A 109.4 . . ?
C31 C32 H32A 109.4 . . ?
C33 C32 H32B 109.4 . . ?
C31 C32 H32B 109.4 . . ?
H32A C32 H32B 108.0 . . ?
C34 C33 C32 112.6(5) . . ?
C34 C33 H33A 109.1 . . ?
C32 C33 H33A 109.1 . . ?
C34 C33 H33B 109.1 . . ?
C32 C33 H33B 109.1 . . ?
H33A C33 H33B 107.8 . . ?
N29 C34 C33 113.6(5) . . ?
N29 C34 C35 109.2(5) . . ?
C33 C34 C35 111.5(5) . . ?
N29 C34 H34 107.4 . . ?
C33 C34 H34 107.4 . . ?
C35 C34 H34 107.4 . . ?
C34 C35 H35A 109.5 . . ?
C34 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C34 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C30 C36 H36A 109.5 . . ?
C30 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C30 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
O3' Cu2 O3' 180.0 2_667 . ?
O3' Cu2 N9' 97.42(15) 2_667 . ?
O3' Cu2 N9' 82.58(15) . . ?
O3' Cu2 N9' 82.58(15) 2_667 2_667 ?
O3' Cu2 N9' 97.42(15) . 2_667 ?
N9' Cu2 N9' 180.0(2) . 2_667 ?
O1' S1' O2' 119.0(3) . . ?
O1' S1' N1' 108.5(3) . . ?
O2' S1' N1' 107.4(2) . . ?
O1' S1' C2' 105.3(2) . . ?
O2' S1' C2' 106.4(3) . . ?
N1' S1' C2' 110.2(3) . . ?
C7' O3' Cu2 113.0(3) . . ?
S1' N1' H1NC 111.4 . . ?
S1' N1' H1ND 126.6 . . ?
H1NC N1' H1ND 115.8 . . ?
C7' N8' N9' 110.8(4) . . ?
N8' N9' C14' 105.2(4) . . ?
N8' N9' C10' 103.9(4) . . ?
C14' N9' C10' 111.4(4) . . ?
N8' N9' Cu2 107.1(3) . . ?
C14' N9' Cu2 114.1(3) . . ?
C10' N9' Cu2 114.1(3) . . ?
C2' C1' C6' 122.4(5) . . ?
C2' C1' H1' 118.8 . . ?
C6' C1' H1' 118.8 . . ?
C1' C2' C3' 118.1(5) . . ?
C1' C2' S1' 117.4(4) . . ?
C3' C2' S1' 124.5(4) . . ?
C4' C3' C2' 120.2(5) . . ?
C4' C3' Cl1' 117.9(5) . . ?
C2' C3' Cl1' 121.9(5) . . ?
C3' C4' C5' 120.4(6) . . ?
C3' C4' H4' 119.8 . . ?
C5' C4' H4' 119.8 . . ?
C4' C5' C6' 120.6(6) . . ?
C4' C5' H5' 119.7 . . ?
C6' C5' H5' 119.7 . . ?
C1' C6' C5' 118.2(5) . . ?
C1' C6' C7' 118.0(5) . . ?
C5' C6' C7' 123.8(5) . . ?
N8' C7' O3' 126.5(5) . . ?
N8' C7' C6' 118.9(5) . . ?
O3' C7' C6' 114.6(5) . . ?
C11' C10' C16' 111.9(5) . . ?
C11' C10' N9' 112.2(5) . . ?
C16' C10' N9' 109.8(4) . . ?
C11' C10' H10' 107.6 . . ?
C16' C10' H10' 107.6 . . ?
N9' C10' H10' 107.6 . . ?
C10' C11' C12' 112.9(5) . . ?
C10' C11' H11C 109.0 . . ?
C12' C11' H11C 109.0 . . ?
C10' C11' H11D 109.0 . . ?
C12' C11' H11D 109.0 . . ?
H11C C11' H11D 107.8 . . ?
C13' C12' C11' 109.3(5) . . ?
C13' C12' H12A 109.8 . . ?
C11' C12' H12A 109.8 . . ?
C13' C12' H12B 109.8 . . ?
C11' C12' H12B 109.8 . . ?
H12A C12' H12B 108.3 . . ?
C14' C13' C12' 112.7(5) . . ?
C14' C13' H13C 109.0 . . ?
C12' C13' H13C 109.0 . . ?
C14' C13' H13D 109.0 . . ?
C12' C13' H13D 109.0 . . ?
H13C C13' H13D 107.8 . . ?
C13' C14' N9' 111.5(4) . . ?
C13' C14' C15' 112.6(5) . . ?
N9' C14' C15' 110.0(5) . . ?
C13' C14' H14' 107.5 . . ?
N9' C14' H14' 107.5 . . ?
C15' C14' H14' 107.5 . . ?
C14' C15' H15A 109.5 . . ?
C14' C15' H15B 109.5 . . ?
H15A C15' H15B 109.5 . . ?
C14' C15' H15C 109.5 . . ?
H15A C15' H15C 109.5 . . ?
H15B C15' H15C 109.5 . . ?
C10' C16' H16A 109.5 . . ?
C10' C16' H16B 109.5 . . ?
H16A C16' H16B 109.5 . . ?
C10' C16' H16C 109.5 . . ?
H16A C16' H16C 109.5 . . ?
H16B C16' H16C 109.5 . . ?
O6' Cu3 O6' 180.0 . 2_666 ?
O6' Cu3 N29' 97.45(17) . 2_666 ?
O6' Cu3 N29' 82.55(17) 2_666 2_666 ?
O6' Cu3 N29' 82.55(17) . . ?
O6' Cu3 N29' 97.45(17) 2_666 . ?
N29' Cu3 N29' 180.0 2_666 . ?
O4' S2' O5' 119.1(2) . . ?
O4' S2' N2' 108.1(2) . . ?
O5' S2' N2' 107.2(2) . . ?
O4' S2' C22' 105.6(2) . . ?
O5' S2' C22' 107.5(2) . . ?
N2' S2' C22' 109.1(2) . . ?
C27' O6' Cu3 112.8(3) . . ?
S2' N2' H2ND 117.7 . . ?
S2' N2' H2NC 115.9 . . ?
H2ND N2' H2NC 116.1 . . ?
C27' N28' N29' 110.4(5) . . ?
N28' N29' C30' 104.4(4) . . ?
N28' N29' C34' 103.7(4) . . ?
C30' N29' C34' 110.8(5) . . ?
N28' N29' Cu3 106.8(3) . . ?
C30' N29' Cu3 117.6(4) . . ?
C34' N29' Cu3 112.2(4) . . ?
C22' C21' C26' 121.2(5) . . ?
C22' C21' H21' 119.4 . . ?
C26' C21' H21' 119.4 . . ?
C21' C22' C23' 118.3(5) . . ?
C21' C22' S2' 117.1(4) . . ?
C23' C22' S2' 124.6(4) . . ?
C24' C23' C22' 120.8(5) . . ?
C24' C23' Cl2' 118.0(4) . . ?
C22' C23' Cl2' 121.2(4) . . ?
C23' C24' C25' 119.8(5) . . ?
C23' C24' H24' 120.1 . . ?
C25' C24' H24' 120.1 . . ?
C26' C25' C24' 120.8(5) . . ?
C26' C25' H25' 119.6 . . ?
C24' C25' H25' 119.6 . . ?
C25' C26' C21' 119.1(5) . . ?
C25' C26' C27' 124.0(5) . . ?
C21' C26' C27' 116.9(5) . . ?
O6' C27' N28' 127.4(5) . . ?
O6' C27' C26' 115.1(5) . . ?
N28' C27' C26' 117.5(5) . . ?
C31' C30' C36' 112.5(6) . . ?
C31' C30' N29' 112.0(6) . . ?
C36' C30' N29' 107.5(5) . . ?
C31' C30' H30' 108.2 . . ?
C36' C30' H30' 108.2 . . ?
N29' C30' H30' 108.2 . . ?
C30' C31' C32' 113.1(6) . . ?
C30' C31' H31C 109.0 . . ?
C32' C31' H31C 109.0 . . ?
C30' C31' H31D 109.0 . . ?
C32' C31' H31D 109.0 . . ?
H31C C31' H31D 107.8 . . ?
C33' C32' C31' 109.9(6) . . ?
C33' C32' H32C 109.7 . . ?
C31' C32' H32C 109.7 . . ?
C33' C32' H32D 109.7 . . ?
C31' C32' H32D 109.7 . . ?
H32C C32' H32D 108.2 . . ?
C34' C33' C32' 111.6(7) . . ?
C34' C33' H33C 109.3 . . ?
C32' C33' H33C 109.3 . . ?
C34' C33' H33D 109.3 . . ?
C32' C33' H33D 109.3 . . ?
H33C C33' H33D 108.0 . . ?
C35' C34' C33' 112.6(6) . . ?
C35' C34' N29' 110.6(5) . . ?
C33' C34' N29' 111.9(6) . . ?
C35' C34' H34' 107.1 . . ?
C33' C34' H34' 107.1 . . ?
N29' C34' H34' 107.1 . . ?
C34' C35' H35D 109.5 . . ?
C34' C35' H35E 109.5 . . ?
H35D C35' H35E 109.5 . . ?
C34' C35' H35F 109.5 . . ?
H35D C35' H35F 109.5 . . ?
H35E C35' H35F 109.5 . . ?
C30' C36' H36D 109.5 . . ?
C30' C36' H36E 109.5 . . ?
H36D C36' H36E 109.5 . . ?
C30' C36' H36F 109.5 . . ?
H36D C36' H36F 109.5 . . ?
H36E C36' H36F 109.5 . . ?

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
N29 Cu1 O3 C7 177.1(4) . . . . ?
N9 Cu1 O3 C7 -4.0(4) . . . . ?
N29 Cu1 O6 C27 -0.1(4) . . . . ?
N9 Cu1 O6 C27 -179.1(4) . . . . ?
C7 N8 N9 C14 120.4(5) . . . . ?
C7 N8 N9 C10 -124.5(5) . . . . ?
C7 N8 N9 Cu1 -1.2(5) . . . . ?
C27 N28 N29 C34 -124.9(5) . . . . ?
C27 N28 N29 C30 120.0(5) . . . . ?
C27 N28 N29 Cu1 -2.2(6) . . . . ?
C6 C1 C2 C3 0.3(8) . . . . ?
C6 C1 C2 S1 -177.7(4) . . . . ?
O1 S1 C2 C1 -11.9(5) . . . . ?
O2 S1 C2 C1 116.7(5) . . . . ?
N1 S1 C2 C1 -127.9(5) . . . . ?
O1 S1 C2 C3 170.2(5) . . . . ?
O2 S1 C2 C3 -61.2(5) . . . . ?
N1 S1 C2 C3 54.2(6) . . . . ?
C1 C2 C3 C4 1.5(9) . . . . ?
S1 C2 C3 C4 179.4(4) . . . . ?
C1 C2 C3 Cl1 -178.9(4) . . . . ?
S1 C2 C3 Cl1 -1.0(7) . . . . ?
C2 C3 C4 C5 -2.0(9) . . . . ?
Cl1 C3 C4 C5 178.4(5) . . . . ?
C3 C4 C5 C6 0.7(9) . . . . ?
C4 C5 C6 C1 1.1(9) . . . . ?
C4 C5 C6 C7 -177.0(5) . . . . ?
C2 C1 C6 C5 -1.6(8) . . . . ?
C2 C1 C6 C7 176.6(5) . . . . ?
Cu1 O3 C7 N8 5.0(7) . . . . ?
Cu1 O3 C7 C6 -174.2(4) . . . . ?
N9 N8 C7 O3 -2.3(8) . . . . ?
N9 N8 C7 C6 176.9(4) . . . . ?
C5 C6 C7 O3 167.7(5) . . . . ?
C1 C6 C7 O3 -10.3(7) . . . . ?
C5 C6 C7 N8 -11.6(8) . . . . ?
C1 C6 C7 N8 170.4(5) . . . . ?
N8 N9 C10 C11 -167.4(5) . . . . ?
C14 N9 C10 C11 -55.1(6) . . . . ?
Cu1 N9 C10 C11 75.0(5) . . . . ?
N8 N9 C10 C16 66.7(5) . . . . ?
C14 N9 C10 C16 179.0(5) . . . . ?
Cu1 N9 C10 C16 -50.9(6) . . . . ?
C16 C10 C11 C12 178.2(5) . . . . ?
N9 C10 C11 C12 54.0(7) . . . . ?
C10 C11 C12 C13 -51.5(7) . . . . ?
C11 C12 C13 C14 53.5(7) . . . . ?
C12 C13 C14 C15 178.1(5) . . . . ?
C12 C13 C14 N9 -57.1(7) . . . . ?
N8 N9 C14 C13 167.4(5) . . . . ?
C10 N9 C14 C13 55.8(6) . . . . ?
Cu1 N9 C14 C13 -75.4(5) . . . . ?
N8 N9 C14 C15 -66.1(6) . . . . ?
C10 N9 C14 C15 -177.7(5) . . . . ?
Cu1 N9 C14 C15 51.1(5) . . . . ?
C26 C21 C22 C23 -0.3(8) . . . . ?
C26 C21 C22 S2 175.6(4) . . . . ?
O5 S2 C22 C21 -111.9(5) . . . . ?
O4 S2 C22 C21 16.5(5) . . . . ?
N2 S2 C22 C21 131.6(5) . . . . ?
O5 S2 C22 C23 63.8(5) . . . . ?
O4 S2 C22 C23 -167.9(5) . . . . ?
N2 S2 C22 C23 -52.8(5) . . . . ?
C21 C22 C23 C24 -1.9(8) . . . . ?
S2 C22 C23 C24 -177.5(4) . . . . ?
C21 C22 C23 Cl2 174.9(4) . . . . ?
S2 C22 C23 Cl2 -0.7(7) . . . . ?
C22 C23 C24 C25 1.9(9) . . . . ?
Cl2 C23 C24 C25 -175.0(4) . . . . ?
C23 C24 C25 C26 0.3(9) . . . . ?
C24 C25 C26 C21 -2.4(9) . . . . ?
C24 C25 C26 C27 173.3(5) . . . . ?
C22 C21 C26 C25 2.5(9) . . . . ?
C22 C21 C26 C27 -173.5(5) . . . . ?
N29 N28 C27 O6 2.6(9) . . . . ?
N29 N28 C27 C26 -175.6(5) . . . . ?
Cu1 O6 C27 N28 -1.5(8) . . . . ?
Cu1 O6 C27 C26 176.7(4) . . . . ?
C25 C26 C27 N28 6.0(9) . . . . ?
C21 C26 C27 N28 -178.2(6) . . . . ?
C25 C26 C27 O6 -172.4(5) . . . . ?
C21 C26 C27 O6 3.4(8) . . . . ?
N28 N29 C30 C31 167.5(5) . . . . ?
C34 N29 C30 C31 55.7(7) . . . . ?
Cu1 N29 C30 C31 -75.5(6) . . . . ?
N28 N29 C30 C36 -66.7(6) . . . . ?
C34 N29 C30 C36 -178.5(5) . . . . ?
Cu1 N29 C30 C36 50.3(6) . . . . ?
N29 C30 C31 C32 -56.0(7) . . . . ?
C36 C30 C31 C32 179.1(5) . . . . ?
C30 C31 C32 C33 52.0(8) . . . . ?
C31 C32 C33 C34 -50.0(8) . . . . ?
N28 N29 C34 C33 -165.0(5) . . . . ?
C30 N29 C34 C33 -54.1(7) . . . . ?
Cu1 N29 C34 C33 77.2(6) . . . . ?
N28 N29 C34 C35 69.9(6) . . . . ?
C30 N29 C34 C35 -179.1(5) . . . . ?
Cu1 N29 C34 C35 -47.8(6) . . . . ?
C32 C33 C34 N29 52.5(7) . . . . ?
C32 C33 C34 C35 176.3(5) . . . . ?
N9' Cu2 O3' C7' 0.8(4) . . . . ?
N9' Cu2 O3' C7' -179.2(4) 2_667 . . . ?
C7' N8' N9' C14' 123.2(5) . . . . ?
C7' N8' N9' C10' -119.7(5) . . . . ?
C7' N8' N9' Cu2 1.4(5) . . . . ?
C6' C1' C2' C3' 0.1(8) . . . . ?
C6' C1' C2' S1' -178.3(4) . . . . ?
O1' S1' C2' C1' -14.7(5) . . . . ?
O2' S1' C2' C1' 112.5(4) . . . . ?
N1' S1' C2' C1' -131.4(4) . . . . ?
O1' S1' C2' C3' 167.1(5) . . . . ?
O2' S1' C2' C3' -65.7(5) . . . . ?
N1' S1' C2' C3' 50.3(5) . . . . ?
C1' C2' C3' C4' -1.8(8) . . . . ?
S1' C2' C3' C4' 176.5(4) . . . . ?
C1' C2' C3' Cl1' 177.3(4) . . . . ?
S1' C2' C3' Cl1' -4.5(7) . . . . ?
C2' C3' C4' C5' 0.5(9) . . . . ?
Cl1' C3' C4' C5' -178.6(4) . . . . ?
C3' C4' C5' C6' 2.5(9) . . . . ?
C2' C1' C6' C5' 2.8(8) . . . . ?
C2' C1' C6' C7' -178.6(5) . . . . ?
C4' C5' C6' C1' -4.1(8) . . . . ?
C4' C5' C6' C7' 177.4(5) . . . . ?
N9' N8' C7' O3' -0.9(7) . . . . ?
N9' N8' C7' C6' 179.9(4) . . . . ?
Cu2 O3' C7' N8' -0.1(7) . . . . ?
Cu2 O3' C7' C6' 179.1(3) . . . . ?
C1' C6' C7' N8' 164.3(5) . . . . ?
C5' C6' C7' N8' -17.2(8) . . . . ?
C1' C6' C7' O3' -14.9(7) . . . . ?
C5' C6' C7' O3' 163.6(5) . . . . ?
N8' N9' C10' C11' -165.2(5) . . . . ?
C14' N9' C10' C11' -52.4(6) . . . . ?
Cu2 N9' C10' C11' 78.5(5) . . . . ?
N8' N9' C10' C16' 69.7(5) . . . . ?
C14' N9' C10' C16' -177.5(4) . . . . ?
Cu2 N9' C10' C16' -46.6(5) . . . . ?
C16' C10' C11' C12' 177.7(5) . . . . ?
N9' C10' C11' C12' 53.8(7) . . . . ?
C10' C11' C12' C13' -54.2(7) . . . . ?
C11' C12' C13' C14' 55.3(7) . . . . ?
C12' C13' C14' N9' -56.0(7) . . . . ?
C12' C13' C14' C15' 179.7(5) . . . . ?
N8' N9' C14' C13' 165.2(5) . . . . ?
C10' N9' C14' C13' 53.3(6) . . . . ?
Cu2 N9' C14' C13' -77.7(5) . . . . ?
N8' N9' C14' C15' -69.1(5) . . . . ?
C10' N9' C14' C15' 178.9(4) . . . . ?
Cu2 N9' C14' C15' 48.0(5) . . . . ?
N29' Cu3 O6' C27' 180.0(4) 2_666 . . . ?
N29' Cu3 O6' C27' 0.0(4) . . . . ?
C27' N28' N29' C30' 123.1(5) . . . . ?
C27' N28' N29' C34' -120.8(5) . . . . ?
C27' N28' N29' Cu3 -2.2(5) . . . . ?
C26' C21' C22' C23' 0.2(8) . . . . ?
C26' C21' C22' S2' -177.9(4) . . . . ?
O4' S2' C22' C21' 11.6(5) . . . . ?
O5' S2' C22' C21' -116.6(4) . . . . ?
N2' S2' C22' C21' 127.6(4) . . . . ?
O4' S2' C22' C23' -166.4(5) . . . . ?
O5' S2' C22' C23' 65.5(5) . . . . ?
N2' S2' C22' C23' -50.4(5) . . . . ?
C21' C22' C23' C24' -3.0(8) . . . . ?
S2' C22' C23' C24' 174.9(4) . . . . ?
C21' C22' C23' Cl2' 178.7(4) . . . . ?
S2' C22' C23' Cl2' -3.3(7) . . . . ?
C22' C23' C24' C25' 3.8(9) . . . . ?
Cl2' C23' C24' C25' -177.9(4) . . . . ?
C23' C24' C25' C26' -1.7(9) . . . . ?
C24' C25' C26' C21' -1.2(8) . . . . ?
C24' C25' C26' C27' 179.8(5) . . . . ?
C22' C21' C26' C25' 1.9(8) . . . . ?
C22' C21' C26' C27' -179.0(5) . . . . ?
Cu3 O6' C27' N28' -1.6(7) . . . . ?
Cu3 O6' C27' C26' 178.2(3) . . . . ?
N29' N28' C27' O6' 2.7(8) . . . . ?
N29' N28' C27' C26' -177.2(4) . . . . ?
C25' C26' C27' O6' -177.1(5) . . . . ?
C21' C26' C27' O6' 3.8(7) . . . . ?
C25' C26' C27' N28' 2.7(8) . . . . ?
C21' C26' C27' N28' -176.3(5) . . . . ?
N28' N29' C30' C31' 162.4(6) . . . . ?
C34' N29' C30' C31' 51.4(7) . . . . ?
Cu3 N29' C30' C31' -79.5(6) . . . . ?
N28' N29' C30' C36' -73.5(6) . . . . ?
C34' N29' C30' C36' 175.5(5) . . . . ?
Cu3 N29' C30' C36' 44.6(6) . . . . ?
C36' C30' C31' C32' -175.2(7) . . . . ?
N29' C30' C31' C32' -54.0(9) . . . . ?
C30' C31' C32' C33' 55.5(9) . . . . ?
C31' C32' C33' C34' -56.5(8) . . . . ?
C32' C33' C34' C35' -178.4(6) . . . . ?
C32' C33' C34' N29' 56.3(8) . . . . ?
N28' N29' C34' C35' 68.8(6) . . . . ?
C30' N29' C34' C35' -179.7(6) . . . . ?
Cu3 N29' C34' C35' -46.0(6) . . . . ?
N28' N29' C34' C33' -164.8(6) . . . . ?
C30' N29' C34' C33' -53.2(7) . . . . ?
Cu3 N29' C34' C33' 80.4(6) . . . . ?

_refine_diff_density_max         0.557
_refine_diff_density_min         -0.566
_refine_diff_density_rms         0.083

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 2099757'
loop_
_audit_author_name
_audit_author_address
'Petra Bombicz'
;Centre for Structural Science, Research Centre for Natural Sciences
Hungary
;
_audit_update_record             
;
2021-07-27 deposited with the CCDC.	2021-08-30 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT601_shelx               
;
PROBLEM: Unit Cell Contains Solvent Accessible VOIDS of .        482 Ang**3
RESPONSE: It is proved by thermal analyses that around less than 3% solvent remains in the voids. 
;
# Added during the CSD deposition process: Wednesday 28 July 2021 12:06 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
trans-bis(4-chloro-N-(2,6-dimethylpiperidin-1-yl)-3-sulfamoylbenzamide)-copper(II)
_chemical_name_common            'clopamide copper(II)'
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H38 Cl2 Cu N6 O6 S2'
_chemical_formula_sum            'C28 H38 Cl2 Cu N6 O6 S2'
_chemical_formula_weight         753.20

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'
Cu Cu -1.9646 0.5888 '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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3 :H'
_space_group_name_Hall           '-R 3'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   23.078(3)
_cell_length_b                   23.078(3)
_cell_length_c                   18.3291(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     8454(2)
_cell_formula_units_Z            9
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    10425
_cell_measurement_theta_min      3.270
_cell_measurement_theta_max      68.035

_exptl_crystal_description       Brown
_exptl_crystal_colour            Chunk
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'Not measured'
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_F_000             3519
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    3.544
_shelx_estimated_absorpt_T_min   0.718
_shelx_estimated_absorpt_T_max   0.843
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.962
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_process_details   
;
 T.Higashi, Numerical Absorption Correction, NUMABS, 2002
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  Graphite
_diffrn_radiation_detector       RX
_diffrn_measurement_device_type  R-AXIS-RAPID
_diffrn_measurement_method       dtprofit.ref
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            18855
_diffrn_reflns_av_unetI/netI     0.1494
_diffrn_reflns_av_R_equivalents  0.1176
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.272
_diffrn_reflns_theta_max         68.152
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3429
_reflns_number_gt                1580
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2006)'
_computing_publication_material  
;
MERCURY (Macrae et al., 2006); Platon (Spek,
 2009
;
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0565P)²+32.8669P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3429
_refine_ls_number_parameters     207
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2142
_refine_ls_R_factor_gt           0.1033
_refine_ls_wR_factor_ref         0.2052
_refine_ls_wR_factor_gt          0.1672
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.094
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
Cu1 Cu 0.333333 0.166667 -0.333333 0.0546(6) Uani 1 2 d S . P . .
Cl1 Cl 0.22124(12) 0.04733(11) 0.10466(10) 0.0804(8) Uani 1 1 d . . . . .
S1 S 0.35651(12) 0.18038(11) 0.04277(11) 0.0588(7) Uani 1 1 d . . . . .
O1 O 0.4103(3) 0.2218(3) -0.0051(3) 0.0675(16) Uani 1 1 d . . . . .
O2 O 0.3238(3) 0.2088(3) 0.0837(2) 0.0623(16) Uani 1 1 d . . . . .
O3 O 0.3189(3) 0.1518(3) -0.2332(2) 0.0561(15) Uani 1 1 d . . . . .
N1 N 0.3819(3) 0.1460(3) 0.0983(3) 0.069(2) Uani 1 1 d . . . . .
H1A H 0.366778 0.134439 0.146695 0.083 Uiso 1 1 d R U . . .
H1B H 0.412638 0.134719 0.081305 0.083 Uiso 1 1 d R U . . .
N8 N 0.2389(3) 0.0450(3) -0.2623(3) 0.0534(18) Uani 1 1 d . . . . .
N9 N 0.2594(3) 0.0688(3) -0.3381(3) 0.064(2) Uani 1 1 d . . . . .
C1 C 0.3030(4) 0.1249(4) -0.0881(4) 0.053(2) Uani 1 1 d . . . . .
H1 H 0.341305 0.163687 -0.106318 0.064 Uiso 1 1 calc R U . . .
C2 C 0.2943(4) 0.1171(4) -0.0137(4) 0.046(2) Uani 1 1 d . . . . .
C3 C 0.2367(5) 0.0611(4) 0.0127(4) 0.056(2) Uani 1 1 d . . . . .
C4 C 0.1915(4) 0.0145(4) -0.0359(4) 0.062(2) Uani 1 1 d . . . . .
H4 H 0.152957 -0.024249 -0.018082 0.074 Uiso 1 1 calc R U . . .
C5 C 0.2024(4) 0.0242(4) -0.1106(4) 0.059(2) Uani 1 1 d . . . . .
H5 H 0.170391 -0.007453 -0.143461 0.070 Uiso 1 1 calc R U . . .
C6 C 0.2584(4) 0.0787(4) -0.1375(4) 0.049(2) Uani 1 1 d . . . . .
C7 C 0.2725(4) 0.0920(4) -0.2171(4) 0.048(2) Uani 1 1 d . . . . .
C10 C 0.2845(5) 0.0229(4) -0.3692(4) 0.072(3) Uani 1 1 d . . . . .
H10 H 0.248915 -0.024292 -0.359366 0.087 Uiso 1 1 calc R U . . .
C11 C 0.2941(5) 0.0299(5) -0.4487(5) 0.096(4) Uani 1 1 d . . . . .
H11A H 0.308856 -0.001224 -0.466202 0.115 Uiso 1 1 calc R U . . .
H11B H 0.329715 0.076026 -0.460307 0.115 Uiso 1 1 calc R U . . .
C12 C 0.2302(7) 0.0151(6) -0.4882(5) 0.129(5) Uani 1 1 d . . . . .
H12A H 0.196191 -0.032689 -0.482056 0.155 Uiso 1 1 calc R U . . .
H12B H 0.239435 0.024120 -0.540943 0.155 Uiso 1 1 calc R U . . .
C13 C 0.2031(5) 0.0595(6) -0.4569(5) 0.109(4) Uani 1 1 d . . . . .
H13A H 0.234341 0.106797 -0.469867 0.131 Uiso 1 1 calc R U . . .
H13B H 0.159319 0.046285 -0.479639 0.131 Uiso 1 1 calc R U . . .
C14 C 0.1949(5) 0.0534(5) -0.3745(4) 0.084(3) Uani 1 1 d . . . . .
H14 H 0.160152 0.006400 -0.362178 0.101 Uiso 1 1 calc R U . . .
C15 C 0.1729(5) 0.1002(5) -0.3445(5) 0.101(3) Uani 1 1 d . . . . .
H15A H 0.170678 0.096986 -0.291167 0.152 Uiso 1 1 calc R U . . .
H15B H 0.128648 0.087765 -0.363984 0.152 Uiso 1 1 calc R U . . .
H15C H 0.205113 0.146182 -0.358932 0.152 Uiso 1 1 calc R U . . .
C16 C 0.3448(5) 0.0339(5) -0.3306(5) 0.092(3) Uani 1 1 d . . . . .
H16A H 0.380900 0.079956 -0.338783 0.137 Uiso 1 1 calc R U . . .
H16B H 0.358390 0.002634 -0.348845 0.137 Uiso 1 1 calc R U . . .
H16C H 0.335297 0.026596 -0.278202 0.137 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
Cu1 O3 1.866(5) . ?
Cu1 O3 1.866(5) 13_554 ?
Cu1 N9 2.041(6) . ?
Cu1 N9 2.041(6) 13_554 ?
Cl1 C3 1.719(8) . ?
S1 O1 1.427(5) . ?
S1 O2 1.434(5) . ?
S1 N1 1.572(6) . ?
S1 C2 1.780(8) . ?
O3 C7 1.289(8) . ?
N1 H1A 0.9413 . ?
N1 H1B 0.9244 . ?
N8 C7 1.275(8) . ?
N8 N9 1.481(7) . ?
N9 C14 1.503(10) . ?
N9 C10 1.547(10) . ?
C1 C2 1.377(9) . ?
C1 C6 1.385(9) . ?
C1 H1 0.9500 . ?
C2 C3 1.398(10) . ?
C3 C4 1.384(10) . ?
C4 C5 1.390(9) . ?
C4 H4 0.9500 . ?
C5 C6 1.368(10) . ?
C5 H5 0.9500 . ?
C6 C7 1.494(10) . ?
C10 C16 1.464(11) . ?
C10 C11 1.470(10) . ?
C10 H10 1.0000 . ?
C11 C12 1.519(14) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.552(15) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.521(11) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.508(12) . ?
C14 H14 1.0000 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

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
O3 Cu1 O3 180.0 . 13_554 ?
O3 Cu1 N9 82.3(2) . . ?
O3 Cu1 N9 97.7(2) 13_554 . ?
O3 Cu1 N9 97.7(2) . 13_554 ?
O3 Cu1 N9 82.3(2) 13_554 13_554 ?
N9 Cu1 N9 180.0 . 13_554 ?
O1 S1 O2 119.6(3) . . ?
O1 S1 N1 108.5(3) . . ?
O2 S1 N1 107.8(3) . . ?
O1 S1 C2 105.5(3) . . ?
O2 S1 C2 106.6(3) . . ?
N1 S1 C2 108.3(4) . . ?
C7 O3 Cu1 113.5(5) . . ?
S1 N1 H1A 125.1 . . ?
S1 N1 H1B 117.1 . . ?
H1A N1 H1B 117.7 . . ?
C7 N8 N9 110.4(6) . . ?
N8 N9 C14 103.4(6) . . ?
N8 N9 C10 104.6(6) . . ?
C14 N9 C10 109.9(7) . . ?
N8 N9 Cu1 107.8(4) . . ?
C14 N9 Cu1 117.5(6) . . ?
C10 N9 Cu1 112.4(5) . . ?
C2 C1 C6 122.9(8) . . ?
C2 C1 H1 118.6 . . ?
C6 C1 H1 118.6 . . ?
C1 C2 C3 118.2(7) . . ?
C1 C2 S1 117.6(6) . . ?
C3 C2 S1 124.1(6) . . ?
C4 C3 C2 119.6(7) . . ?
C4 C3 Cl1 118.8(7) . . ?
C2 C3 Cl1 121.6(7) . . ?
C3 C4 C5 120.3(8) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C6 C5 C4 120.9(8) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C1 118.0(7) . . ?
C5 C6 C7 123.3(8) . . ?
C1 C6 C7 118.6(8) . . ?
N8 C7 O3 126.1(7) . . ?
N8 C7 C6 118.9(8) . . ?
O3 C7 C6 115.0(7) . . ?
C16 C10 C11 112.5(9) . . ?
C16 C10 N9 110.5(7) . . ?
C11 C10 N9 112.2(8) . . ?
C16 C10 H10 107.1 . . ?
C11 C10 H10 107.1 . . ?
N9 C10 H10 107.1 . . ?
C10 C11 C12 111.9(9) . . ?
C10 C11 H11A 109.2 . . ?
C12 C11 H11A 109.2 . . ?
C10 C11 H11B 109.2 . . ?
C12 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C11 C12 C13 110.0(9) . . ?
C11 C12 H12A 109.7 . . ?
C13 C12 H12A 109.7 . . ?
C11 C12 H12B 109.7 . . ?
C13 C12 H12B 109.7 . . ?
H12A C12 H12B 108.2 . . ?
C14 C13 C12 112.2(9) . . ?
C14 C13 H13A 109.2 . . ?
C12 C13 H13A 109.2 . . ?
C14 C13 H13B 109.2 . . ?
C12 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
N9 C14 C15 108.5(8) . . ?
N9 C14 C13 110.9(8) . . ?
C15 C14 C13 111.5(9) . . ?
N9 C14 H14 108.6 . . ?
C15 C14 H14 108.6 . . ?
C13 C14 H14 108.6 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C10 C16 H16A 109.5 . . ?
C10 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C10 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

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
N9 Cu1 O3 C7 -0.8(5) . . . . ?
N9 Cu1 O3 C7 179.2(5) 13_554 . . . ?
C7 N8 N9 C14 -124.6(7) . . . . ?
C7 N8 N9 C10 120.3(7) . . . . ?
C7 N8 N9 Cu1 0.5(7) . . . . ?
C6 C1 C2 C3 -2.0(11) . . . . ?
C6 C1 C2 S1 179.2(6) . . . . ?
O1 S1 C2 C1 -10.0(7) . . . . ?
O2 S1 C2 C1 118.2(6) . . . . ?
N1 S1 C2 C1 -126.0(6) . . . . ?
O1 S1 C2 C3 171.4(6) . . . . ?
O2 S1 C2 C3 -60.4(7) . . . . ?
N1 S1 C2 C3 55.4(7) . . . . ?
C1 C2 C3 C4 1.8(11) . . . . ?
S1 C2 C3 C4 -179.6(6) . . . . ?
C1 C2 C3 Cl1 -179.6(5) . . . . ?
S1 C2 C3 Cl1 -1.0(10) . . . . ?
C2 C3 C4 C5 -1.6(12) . . . . ?
Cl1 C3 C4 C5 179.7(6) . . . . ?
C3 C4 C5 C6 1.7(12) . . . . ?
C4 C5 C6 C1 -1.9(12) . . . . ?
C4 C5 C6 C7 -179.5(7) . . . . ?
C2 C1 C6 C5 2.1(12) . . . . ?
C2 C1 C6 C7 179.8(7) . . . . ?
N9 N8 C7 O3 -1.3(11) . . . . ?
N9 N8 C7 C6 178.9(6) . . . . ?
Cu1 O3 C7 N8 1.5(10) . . . . ?
Cu1 O3 C7 C6 -178.7(5) . . . . ?
C5 C6 C7 N8 -14.8(11) . . . . ?
C1 C6 C7 N8 167.6(7) . . . . ?
C5 C6 C7 O3 165.4(8) . . . . ?
C1 C6 C7 O3 -12.2(10) . . . . ?
N8 N9 C10 C16 -65.4(8) . . . . ?
C14 N9 C10 C16 -175.9(7) . . . . ?
Cu1 N9 C10 C16 51.3(8) . . . . ?
N8 N9 C10 C11 168.1(7) . . . . ?
C14 N9 C10 C11 57.7(9) . . . . ?
Cu1 N9 C10 C11 -75.2(8) . . . . ?
C16 C10 C11 C12 177.3(9) . . . . ?
N9 C10 C11 C12 -57.3(11) . . . . ?
C10 C11 C12 C13 54.4(11) . . . . ?
C11 C12 C13 C14 -53.3(12) . . . . ?
N8 N9 C14 C15 70.3(8) . . . . ?
C10 N9 C14 C15 -178.4(7) . . . . ?
Cu1 N9 C14 C15 -48.2(8) . . . . ?
N8 N9 C14 C13 -166.9(8) . . . . ?
C10 N9 C14 C13 -55.6(10) . . . . ?
Cu1 N9 C14 C13 74.5(9) . . . . ?
C12 C13 C14 N9 55.2(12) . . . . ?
C12 C13 C14 C15 176.3(9) . . . . ?

_refine_diff_density_max         0.553
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.077

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC4
_database_code_depnum_ccdc_archive 'CCDC 2099758'
loop_
_audit_author_name
_audit_author_address
'Petra Bombicz'
;Centre for Structural Science, Research Centre for Natural Sciences
Hungary
;
_audit_update_record             
;
2021-07-27 deposited with the CCDC.	2021-08-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
'trans-bis(4-chloro-N-(2,6-dimethylpiperidin-1-yl)-3-sulfamoylbenzamide)-copper(II) dichloromethane solvate'
_chemical_name_common            'clopamide copper(II) dichloromethane'
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H38 Cl2 Cu N6 O6 S2, 2(C H2 Cl2)'
_chemical_formula_sum            'C30 H42 Cl6 Cu N6 O6 S2'
_chemical_formula_weight         923.05

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'
Cu Cu -1.9646 0.5888 '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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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.
;

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'

_cell_length_a                   26.699(2)
_cell_length_b                   9.8941(8)
_cell_length_c                   15.6876(14)
_cell_angle_alpha                90
_cell_angle_beta                 104.750(7)
_cell_angle_gamma                90
_cell_volume                     4007.5(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    128(2)
_cell_measurement_reflns_used    15767
_cell_measurement_theta_min      3.425
_cell_measurement_theta_max      68.360

_exptl_crystal_description       Prism
_exptl_crystal_colour            Brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'Not measured'
_exptl_crystal_density_diffrn    1.530
_exptl_crystal_F_000             1900
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    5.833
_shelx_estimated_absorpt_T_min   0.323
_shelx_estimated_absorpt_T_max   0.593
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.783
_exptl_absorpt_correction_T_max  0.892
_exptl_absorpt_process_details   
;
 T.Higashi, Numerical Absorption Correction, NUMABS, 2002
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      128(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   'NORMAL-focus sealed tube'
_diffrn_radiation_monochromator  Graphite
_diffrn_radiation_detector       RX
_diffrn_measurement_device_type  R-AXIS-RAPID
_diffrn_measurement_method       dtprofit.ref
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            24441
_diffrn_reflns_av_unetI/netI     0.0784
_diffrn_reflns_av_R_equivalents  0.0901
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.424
_diffrn_reflns_theta_max         68.186
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3661
_reflns_number_gt                2601
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2006)'
_computing_publication_material  
;
MERCURY (Macrae et al., 2006); Platon (Spek,
 2009
;
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0466P)²+80.6326P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3661
_refine_ls_number_parameters     234
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1623
_refine_ls_R_factor_gt           0.1231
_refine_ls_wR_factor_ref         0.2539
_refine_ls_wR_factor_gt          0.2351
_refine_ls_goodness_of_fit_ref   1.151
_refine_ls_restrained_S_all      1.151
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
Cu1 Cu 0.250000 0.250000 0.000000 0.0628(7) Uani 1 2 d S . P . .
Cl1 Cl 0.47561(9) -0.2012(3) 0.36802(16) 0.0532(7) Uani 1 1 d . . . . .
S1 S 0.43897(9) 0.1130(3) 0.38868(15) 0.0485(7) Uani 1 1 d . . . . .
O1 O 0.4942(2) 0.1185(7) 0.4088(4) 0.0532(19) Uani 1 1 d . . . . .
O2 O 0.4090(3) 0.2326(7) 0.3723(4) 0.059(2) Uani 1 1 d . . . . .
O3 O 0.2970(2) 0.1685(8) 0.0957(4) 0.0547(19) Uani 1 1 d . . . . .
N1 N 0.4240(3) 0.0341(9) 0.4671(4) 0.050(2) Uani 1 1 d . . . . .
H1A H 0.400516 0.067597 0.491670 0.060 Uiso 1 1 d R U . . .
H1B H 0.439216 -0.043123 0.485910 0.060 Uiso 1 1 d R U . . .
N8 N 0.3192(3) 0.0328(9) -0.0082(5) 0.054(2) Uani 1 1 d . . . . .
N9 N 0.2773(3) 0.1051(10) -0.0712(6) 0.063(3) Uani 1 1 d . . . . .
C1 C 0.3815(3) 0.0722(11) 0.2215(6) 0.043(2) Uani 1 1 d . . . . .
H1 H 0.369884 0.161798 0.226662 0.052 Uiso 1 1 calc R U . . .
C2 C 0.4172(3) 0.0149(9) 0.2917(6) 0.039(2) Uani 1 1 d . . . . .
C3 C 0.4331(3) -0.1198(10) 0.2826(6) 0.044(2) Uani 1 1 d . . . . .
C4 C 0.4139(3) -0.1891(11) 0.2056(6) 0.045(2) Uani 1 1 d . . . . .
H4 H 0.425021 -0.279008 0.199716 0.054 Uiso 1 1 calc R U . . .
C5 C 0.3782(3) -0.1285(11) 0.1360(7) 0.049(3) Uani 1 1 d . . . . .
H5 H 0.364730 -0.177117 0.082928 0.059 Uiso 1 1 calc R U . . .
C6 C 0.3625(3) 0.0025(11) 0.1443(6) 0.046(3) Uani 1 1 d . . . . .
C7 C 0.3232(3) 0.0724(12) 0.0708(6) 0.049(3) Uani 1 1 d . . . . .
C10 C 0.3038(5) 0.1595(17) -0.1409(8) 0.101(6) Uani 1 1 d . . . . .
H10 H 0.326168 0.084381 -0.152632 0.121 Uiso 1 1 calc R U . . .
C11 C 0.2698(6) 0.1920(18) -0.2235(9) 0.105(5) Uani 1 1 d . . . . .
H11A H 0.290693 0.216563 -0.265095 0.126 Uiso 1 1 calc R U . . .
H11B H 0.249136 0.272202 -0.216218 0.126 Uiso 1 1 calc R U . . .
C12 C 0.2342(6) 0.0814(18) -0.2622(10) 0.112(6) Uani 1 1 d . . . . .
H12A H 0.254178 0.004711 -0.277397 0.135 Uiso 1 1 calc R U . . .
H12B H 0.209650 0.113065 -0.317018 0.135 Uiso 1 1 calc R U . . .
C13 C 0.2049(5) 0.0358(18) -0.1975(10) 0.106(6) Uani 1 1 d . . . . .
H13A H 0.182570 0.110478 -0.186798 0.128 Uiso 1 1 calc R U . . .
H13B H 0.182244 -0.041117 -0.222739 0.128 Uiso 1 1 calc R U . . .
C14 C 0.2389(5) -0.0041(18) -0.1163(10) 0.107(6) Uani 1 1 d . . . . .
H14 H 0.260092 -0.080458 -0.130180 0.129 Uiso 1 1 calc R U . . .
C15 C 0.2131(4) -0.0569(13) -0.0437(9) 0.079(4) Uani 1 1 d . . . . .
H15A H 0.193114 0.016048 -0.025979 0.119 Uiso 1 1 calc R U . . .
H15B H 0.240099 -0.087346 0.007580 0.119 Uiso 1 1 calc R U . . .
H15C H 0.190073 -0.132656 -0.067115 0.119 Uiso 1 1 calc R U . . .
C16 C 0.3406(4) 0.2709(13) -0.0971(7) 0.073(4) Uani 1 1 d . . . . .
H16A H 0.357725 0.309358 -0.139915 0.109 Uiso 1 1 calc R U . . .
H16B H 0.366751 0.233257 -0.047222 0.109 Uiso 1 1 calc R U . . .
H16C H 0.321113 0.341761 -0.076042 0.109 Uiso 1 1 calc R U . . .
Cl3 Cl 0.06429(10) 1.0474(3) 0.47939(18) 0.0628(8) Uani 1 1 d . . . . .
Cl4 Cl 0.06885(13) 0.9087(4) 0.3187(2) 0.0886(11) Uani 1 1 d . . . . .
C41 C 0.0342(4) 0.9338(14) 0.3988(8) 0.073(4) Uani 1 1 d . . . . .
H41A H -0.000911 0.967616 0.369664 0.088 Uiso 1 1 calc R U . . .
H41B H 0.030276 0.846116 0.426744 0.088 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
Cu1 O3 1.876(6) 7 ?
Cu1 O3 1.876(6) . ?
Cu1 N9 2.062(10) . ?
Cu1 N9 2.062(10) 7 ?
Cl1 C3 1.720(9) . ?
S1 O2 1.415(7) . ?
S1 O1 1.429(6) . ?
S1 N1 1.592(8) . ?
S1 C2 1.773(10) . ?
O3 C7 1.298(12) . ?
N1 H1A 0.8801 . ?
N1 H1B 0.8800 . ?
N8 C7 1.278(12) . ?
N8 N9 1.474(11) . ?
N9 C14 1.534(15) . ?
N9 C10 1.541(16) . ?
C1 C6 1.374(13) . ?
C1 C2 1.381(11) . ?
C1 H1 0.9500 . ?
C2 C3 1.417(13) . ?
C3 C4 1.370(13) . ?
C4 C5 1.388(13) . ?
C4 H4 0.9500 . ?
C5 C6 1.378(14) . ?
C5 H5 0.9500 . ?
C6 C7 1.514(12) . ?
C10 C11 1.416(16) . ?
C10 C16 1.519(17) . ?
C10 H10 1.0000 . ?
C11 C12 1.475(19) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.50(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.419(18) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.564(19) . ?
C14 H14 1.0000 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
Cl3 C41 1.729(12) . ?
Cl4 C41 1.758(11) . ?
C41 H41A 0.9900 . ?
C41 H41B 0.9900 . ?

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
O3 Cu1 O3 180.0 7 . ?
O3 Cu1 N9 97.0(3) 7 . ?
O3 Cu1 N9 83.0(3) . . ?
O3 Cu1 N9 83.0(3) 7 7 ?
O3 Cu1 N9 97.0(3) . 7 ?
N9 Cu1 N9 180.0 . 7 ?
O2 S1 O1 120.9(5) . . ?
O2 S1 N1 108.0(5) . . ?
O1 S1 N1 107.2(4) . . ?
O2 S1 C2 104.8(4) . . ?
O1 S1 C2 107.7(4) . . ?
N1 S1 C2 107.6(4) . . ?
C7 O3 Cu1 112.1(6) . . ?
S1 N1 H1A 120.0 . . ?
S1 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C7 N8 N9 111.3(9) . . ?
N8 N9 C14 105.7(9) . . ?
N8 N9 C10 103.9(8) . . ?
C14 N9 C10 107.0(10) . . ?
N8 N9 Cu1 106.7(6) . . ?
C14 N9 Cu1 116.9(9) . . ?
C10 N9 Cu1 115.5(9) . . ?
C6 C1 C2 121.5(10) . . ?
C6 C1 H1 119.2 . . ?
C2 C1 H1 119.2 . . ?
C1 C2 C3 117.9(9) . . ?
C1 C2 S1 118.0(8) . . ?
C3 C2 S1 124.1(6) . . ?
C4 C3 C2 120.3(8) . . ?
C4 C3 Cl1 118.5(8) . . ?
C2 C3 Cl1 121.1(7) . . ?
C3 C4 C5 120.3(10) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 119.8(9) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C1 C6 C5 120.1(8) . . ?
C1 C6 C7 118.1(10) . . ?
C5 C6 C7 121.8(9) . . ?
N8 C7 O3 126.7(9) . . ?
N8 C7 C6 117.9(10) . . ?
O3 C7 C6 115.3(8) . . ?
C11 C10 C16 116.0(13) . . ?
C11 C10 N9 115.2(11) . . ?
C16 C10 N9 107.0(11) . . ?
C11 C10 H10 105.9 . . ?
C16 C10 H10 105.9 . . ?
N9 C10 H10 105.9 . . ?
C10 C11 C12 113.8(15) . . ?
C10 C11 H11A 108.8 . . ?
C12 C11 H11A 108.8 . . ?
C10 C11 H11B 108.8 . . ?
C12 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
C11 C12 C13 109.7(11) . . ?
C11 C12 H12A 109.7 . . ?
C13 C12 H12A 109.7 . . ?
C11 C12 H12B 109.7 . . ?
C13 C12 H12B 109.7 . . ?
H12A C12 H12B 108.2 . . ?
C14 C13 C12 111.5(13) . . ?
C14 C13 H13A 109.3 . . ?
C12 C13 H13A 109.3 . . ?
C14 C13 H13B 109.3 . . ?
C12 C13 H13B 109.3 . . ?
H13A C13 H13B 108.0 . . ?
C13 C14 N9 114.7(13) . . ?
C13 C14 C15 116.6(12) . . ?
N9 C14 C15 105.4(11) . . ?
C13 C14 H14 106.5 . . ?
N9 C14 H14 106.5 . . ?
C15 C14 H14 106.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C10 C16 H16A 109.5 . . ?
C10 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C10 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
Cl3 C41 Cl4 112.5(6) . . ?
Cl3 C41 H41A 109.1 . . ?
Cl4 C41 H41A 109.1 . . ?
Cl3 C41 H41B 109.1 . . ?
Cl4 C41 H41B 109.1 . . ?
H41A C41 H41B 107.8 . . ?

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
N9 Cu1 O3 C7 2.8(7) . . . . ?
N9 Cu1 O3 C7 -177.2(7) 7 . . . ?
C7 N8 N9 C14 -119.8(11) . . . . ?
C7 N8 N9 C10 127.7(10) . . . . ?
C7 N8 N9 Cu1 5.3(10) . . . . ?
C6 C1 C2 C3 -1.2(14) . . . . ?
C6 C1 C2 S1 -179.6(8) . . . . ?
O2 S1 C2 C1 5.1(9) . . . . ?
O1 S1 C2 C1 -124.8(8) . . . . ?
N1 S1 C2 C1 119.8(8) . . . . ?
O2 S1 C2 C3 -173.3(8) . . . . ?
O1 S1 C2 C3 56.8(9) . . . . ?
N1 S1 C2 C3 -58.5(9) . . . . ?
C1 C2 C3 C4 1.0(14) . . . . ?
S1 C2 C3 C4 179.3(7) . . . . ?
C1 C2 C3 Cl1 -177.7(7) . . . . ?
S1 C2 C3 Cl1 0.6(12) . . . . ?
C2 C3 C4 C5 -0.7(14) . . . . ?
Cl1 C3 C4 C5 178.0(8) . . . . ?
C3 C4 C5 C6 0.7(15) . . . . ?
C2 C1 C6 C5 1.2(15) . . . . ?
C2 C1 C6 C7 179.4(9) . . . . ?
C4 C5 C6 C1 -0.9(15) . . . . ?
C4 C5 C6 C7 -179.1(9) . . . . ?
N9 N8 C7 O3 -3.8(15) . . . . ?
N9 N8 C7 C6 176.8(8) . . . . ?
Cu1 O3 C7 N8 -0.3(14) . . . . ?
Cu1 O3 C7 C6 179.2(7) . . . . ?
C1 C6 C7 N8 155.5(10) . . . . ?
C5 C6 C7 N8 -26.3(15) . . . . ?
C1 C6 C7 O3 -24.1(14) . . . . ?
C5 C6 C7 O3 154.2(10) . . . . ?
N8 N9 C10 C11 159.1(14) . . . . ?
C14 N9 C10 C11 47.5(18) . . . . ?
Cu1 N9 C10 C11 -84.5(15) . . . . ?
N8 N9 C10 C16 -70.2(13) . . . . ?
C14 N9 C10 C16 178.2(11) . . . . ?
Cu1 N9 C10 C16 46.2(12) . . . . ?
C16 C10 C11 C12 -178.8(13) . . . . ?
N9 C10 C11 C12 -53(2) . . . . ?
C10 C11 C12 C13 54(2) . . . . ?
C11 C12 C13 C14 -56(2) . . . . ?
C12 C13 C14 N9 57(2) . . . . ?
C12 C13 C14 C15 -178.7(14) . . . . ?
N8 N9 C14 C13 -160.8(13) . . . . ?
C10 N9 C14 C13 -50.6(18) . . . . ?
Cu1 N9 C14 C13 80.7(16) . . . . ?
N8 N9 C14 C15 69.6(13) . . . . ?
C10 N9 C14 C15 179.8(11) . . . . ?
Cu1 N9 C14 C15 -48.9(12) . . . . ?

_refine_diff_density_max         0.887
_refine_diff_density_min         -0.619
_refine_diff_density_rms         0.107

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC5
_database_code_depnum_ccdc_archive 'CCDC 2099753'
loop_
_audit_author_name
_audit_author_address
'Petra Bombicz'
;Centre for Structural Science, Research Centre for Natural Sciences
Hungary
;
_audit_update_record             
;
2021-07-27 deposited with the CCDC.	2021-08-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'trans-bis(4-chloro-N-(2,6-dimethylpiperidin-1-yl)-3-sulfamoylbenzamide)-copper(II) diprophanol solvate dihydrate'
_chemical_name_common            'clopamide copper(II) diprophanol dihydrate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H38 Cl2 Cu N6 O6 S2, 2(C3 H8 O), 2(H2 O)'
_chemical_formula_sum            'C34 H58 Cl2 Cu N6 O10 S2'
_chemical_formula_weight         909.42

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.497(5)
_cell_length_b                   8.404(4)
_cell_length_c                   16.310(8)
_cell_angle_alpha                83.113(12)
_cell_angle_beta                 79.445(10)
_cell_angle_gamma                67.366(10)
_cell_volume                     1055.2(10)
_cell_formula_units_Z            1
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    4731
_cell_measurement_theta_min      2.99
_cell_measurement_theta_max      25.47

_exptl_crystal_description       Platelet
_exptl_crystal_colour            Brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'Not measured'
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_F_000             479
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.803
_shelx_estimated_absorpt_T_min   0.690
_shelx_estimated_absorpt_T_max   0.961
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.6700
_exptl_absorpt_correction_T_max  0.9604
_exptl_absorpt_process_details   
;
 T.Higashi, Numerical Absorption Correction, NUMABS, 2002
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      103(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'NORMAL-focus sealed tube'
_diffrn_radiation_monochromator  Graphite
_diffrn_radiation_detector       RX
_diffrn_measurement_device_type  R-AXIS-RAPID
_diffrn_measurement_method       dtprofit.ref
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            16943
_diffrn_reflns_av_unetI/netI     0.1247
_diffrn_reflns_av_R_equivalents  0.1536
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.983
_diffrn_reflns_theta_max         26.920
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.842
_diffrn_measured_fraction_theta_full 0.965
_diffrn_reflns_Laue_measured_fraction_max 0.842
_diffrn_reflns_Laue_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.842
_diffrn_reflns_point_group_measured_fraction_full 0.965
_reflns_number_total             3846
_reflns_number_gt                2585
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Spek, A.L. (2003). J.Appl.Cryst. 36,7-13.'
_computing_publication_material  
;
MERCURY (Macrae et al., 2006); Platon (Spek, 2009)
;
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0992P)²+0.7501P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3846
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1149
_refine_ls_R_factor_gt           0.0856
_refine_ls_wR_factor_ref         0.2365
_refine_ls_wR_factor_gt          0.2121
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
Cu1 Cu 0.5000 0.5000 0.5000 0.0497(4) Uani 1 2 d S . P . .
Cl1 Cl 0.49373(19) 0.2351(2) 0.01940(8) 0.0540(5) Uani 1 1 d . . . . .
S1 S 0.19559(17) 0.24425(18) 0.16920(8) 0.0410(4) Uani 1 1 d . . . . .
O1 O 0.2634(5) 0.0710(5) 0.1510(2) 0.0508(10) Uani 1 1 d . . . . .
O2 O 0.0881(5) 0.2831(5) 0.2429(2) 0.0500(10) Uani 1 1 d . . . . .
O3 O 0.4685(5) 0.4069(5) 0.4080(2) 0.0491(10) Uani 1 1 d . . . . .
N1 N 0.0897(5) 0.3627(6) 0.0917(3) 0.0410(11) Uani 1 1 d . . . . .
H1NA H 0.0068 0.4700 0.0989 0.049 Uiso 1 1 d R U . . .
H1NB H 0.1316 0.3428 0.0394 0.049 Uiso 1 1 d R U . . .
N8 N 0.5864(7) 0.5953(7) 0.3291(3) 0.0556(14) Uani 1 1 d . . . . .
N9 N 0.5981(7) 0.6382(7) 0.4117(3) 0.0624(15) Uani 1 1 d . . . . .
C1 C 0.3863(7) 0.3561(7) 0.2516(3) 0.0400(13) Uani 1 1 d . . . . .
H1 H 0.2997 0.3600 0.2982 0.048 Uiso 1 1 calc R U . . .
C2 C 0.3741(7) 0.3014(7) 0.1779(3) 0.0402(13) Uani 1 1 d . . . . .
C3 C 0.5014(7) 0.2959(7) 0.1136(3) 0.0431(14) Uani 1 1 d . . . . .
C4 C 0.6384(7) 0.3394(8) 0.1254(3) 0.0491(15) Uani 1 1 d . . . . .
H4 H 0.7290 0.3292 0.0801 0.059 Uiso 1 1 calc R U . . .
C5 C 0.6494(8) 0.3953(8) 0.1980(3) 0.0484(15) Uani 1 1 d . . . . .
H5 H 0.7434 0.4253 0.2042 0.058 Uiso 1 1 calc R U . . .
C6 C 0.5186(7) 0.4057(7) 0.2611(3) 0.0430(13) Uani 1 1 d . . . . .
C7 C 0.5250(7) 0.4765(8) 0.3381(3) 0.0461(14) Uani 1 1 d . . . . .
C10 C 0.5090(14) 0.8241(11) 0.4156(5) 0.093(3) Uani 1 1 d . . . . .
H10 H 0.4936 0.8508 0.4753 0.112 Uiso 1 1 calc R U . . .
C11 C 0.612(2) 0.9328(13) 0.3633(5) 0.134(5) Uani 1 1 d . . . . .
H11A H 0.6180 0.9223 0.3029 0.161 Uiso 1 1 calc R U . . .
H11B H 0.5518 1.0562 0.3754 0.161 Uiso 1 1 calc R U . . .
C12 C 0.792(2) 0.870(2) 0.3847(7) 0.159(6) Uani 1 1 d . . . . .
H12A H 0.8594 0.9314 0.3479 0.191 Uiso 1 1 calc R U . . .
H12B H 0.7877 0.8936 0.4432 0.191 Uiso 1 1 calc R U . . .
C13 C 0.8776(17) 0.6823(16) 0.3736(5) 0.125(4) Uani 1 1 d . . . . .
H13A H 0.9978 0.6436 0.3847 0.149 Uiso 1 1 calc R U . . .
H13B H 0.8819 0.6605 0.3148 0.149 Uiso 1 1 calc R U . . .
C14 C 0.7903(12) 0.5780(14) 0.4288(5) 0.086(3) Uani 1 1 d . . . . .
H14 H 0.7843 0.6061 0.4874 0.103 Uiso 1 1 calc R U . . .
C15 C 0.8818(9) 0.3992(14) 0.4241(4) 0.087(3) Uani 1 1 d . . . . .
H15A H 0.9996 0.3703 0.4350 0.131 Uiso 1 1 calc R U . . .
H15B H 0.8857 0.3650 0.3681 0.131 Uiso 1 1 calc R U . . .
H15C H 0.8240 0.3375 0.4657 0.131 Uiso 1 1 calc R U . . .
C16 C 0.3191(15) 0.8784(11) 0.3920(5) 0.113(4) Uani 1 1 d . . . . .
H16A H 0.2616 0.8058 0.4255 0.170 Uiso 1 1 calc R U . . .
H16B H 0.3276 0.8626 0.3326 0.170 Uiso 1 1 calc R U . . .
H16C H 0.2521 0.9998 0.4036 0.170 Uiso 1 1 calc R U . . .
O8 O 0.8727(5) 0.7114(5) 0.0772(2) 0.0427(9) Uani 1 1 d . . . . .
H8 H 0.7801 0.7341 0.1070 0.064 Uiso 1 1 d R U . . .
C41 C 0.9252(8) 0.8548(8) 0.0634(3) 0.0492(15) Uani 1 1 d . . . . .
H41A H 0.8336 0.9553 0.0408 0.059 Uiso 1 1 calc R U . . .
H41B H 1.0306 0.8271 0.0213 0.059 Uiso 1 1 calc R U . . .
C42 C 0.9612(8) 0.9016(8) 0.1423(4) 0.0496(15) Uani 1 1 d . . . . .
H42A H 0.8542 0.9311 0.1834 0.060 Uiso 1 1 calc R U . . .
H42B H 0.9889 1.0069 0.1296 0.060 Uiso 1 1 calc R U . . .
C43 C 1.1124(9) 0.7586(9) 0.1849(4) 0.0644(18) Uani 1 1 d . . . . .
H43A H 1.2204 0.7303 0.1457 0.097 Uiso 1 1 calc R U . . .
H43B H 1.0851 0.6547 0.1999 0.097 Uiso 1 1 calc R U . . .
H43C H 1.1250 0.8026 0.2353 0.097 Uiso 1 1 calc R U . . .
O7 O 0.5816(5) 0.7975(5) 0.1690(2) 0.0589(12) Uani 1 1 d . . . . .
H1O7 H 0.4813 0.8654 0.1582 0.088 Uiso 1 1 d R U . . .
H2O7 H 0.5733 0.7320 0.2132 0.088 Uiso 1 1 d R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
Cu1 O3 1.877(4) 2_666 ?
Cu1 O3 1.877(4) . ?
Cu1 N9 2.006(6) . ?
Cu1 N9 2.006(6) 2_666 ?
Cl1 C3 1.696(5) . ?
S1 O2 1.360(4) . ?
S1 O1 1.391(4) . ?
S1 N1 1.681(5) . ?
S1 C2 1.791(6) . ?
O3 C7 1.316(7) . ?
N1 H1NA 0.9106 . ?
N1 H1NB 0.8716 . ?
N8 C7 1.276(7) . ?
N8 N9 1.466(6) . ?
N9 C10 1.454(10) . ?
N9 C14 1.581(10) . ?
C1 C2 1.372(7) . ?
C1 C6 1.379(8) . ?
C1 H1 0.9500 . ?
C2 C3 1.353(7) . ?
C3 C4 1.398(8) . ?
C4 C5 1.356(8) . ?
C4 H4 0.9500 . ?
C5 C6 1.352(7) . ?
C5 H5 0.9500 . ?
C6 C7 1.471(7) . ?
C10 C11 1.578(14) . ?
C10 C16 1.606(14) . ?
C10 H10 1.0000 . ?
C11 C12 1.507(18) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.477(17) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.481(12) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.406(12) . ?
C14 H14 1.0000 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
O8 C41 1.419(7) . ?
O8 H8 0.8105 . ?
C41 C42 1.503(8) . ?
C41 H41A 0.9900 . ?
C41 H41B 0.9900 . ?
C42 C43 1.586(8) . ?
C42 H42A 0.9900 . ?
C42 H42B 0.9900 . ?
C43 H43A 0.9800 . ?
C43 H43B 0.9800 . ?
C43 H43C 0.9800 . ?
O7 H1O7 0.8597 . ?
O7 H2O7 0.8627 . ?

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
O3 Cu1 O3 180.0 2_666 . ?
O3 Cu1 N9 96.50(19) 2_666 . ?
O3 Cu1 N9 83.50(19) . . ?
O3 Cu1 N9 83.50(19) 2_666 2_666 ?
O3 Cu1 N9 96.50(19) . 2_666 ?
N9 Cu1 N9 180.0(3) . 2_666 ?
O2 S1 O1 115.7(3) . . ?
O2 S1 N1 108.6(2) . . ?
O1 S1 N1 109.1(2) . . ?
O2 S1 C2 105.5(2) . . ?
O1 S1 C2 106.8(2) . . ?
N1 S1 C2 111.1(3) . . ?
C7 O3 Cu1 110.1(4) . . ?
S1 N1 H1NA 122.4 . . ?
S1 N1 H1NB 121.6 . . ?
H1NA N1 H1NB 113.1 . . ?
C7 N8 N9 108.9(5) . . ?
C10 N9 N8 106.3(6) . . ?
C10 N9 C14 111.7(7) . . ?
N8 N9 C14 112.9(5) . . ?
C10 N9 Cu1 114.4(5) . . ?
N8 N9 Cu1 109.3(4) . . ?
C14 N9 Cu1 102.3(5) . . ?
C2 C1 C6 122.9(5) . . ?
C2 C1 H1 118.5 . . ?
C6 C1 H1 118.5 . . ?
C3 C2 C1 116.5(5) . . ?
C3 C2 S1 122.9(4) . . ?
C1 C2 S1 120.6(4) . . ?
C2 C3 C4 119.7(5) . . ?
C2 C3 Cl1 119.7(5) . . ?
C4 C3 Cl1 120.6(4) . . ?
C5 C4 C3 123.7(5) . . ?
C5 C4 H4 118.2 . . ?
C3 C4 H4 118.2 . . ?
C6 C5 C4 116.0(6) . . ?
C6 C5 H5 122.0 . . ?
C4 C5 H5 122.0 . . ?
C5 C6 C1 121.0(5) . . ?
C5 C6 C7 116.0(5) . . ?
C1 C6 C7 123.0(5) . . ?
N8 C7 O3 128.1(5) . . ?
N8 C7 C6 116.5(5) . . ?
O3 C7 C6 115.4(5) . . ?
N9 C10 C11 114.3(8) . . ?
N9 C10 C16 109.3(7) . . ?
C11 C10 C16 112.9(9) . . ?
N9 C10 H10 106.6 . . ?
C11 C10 H10 106.6 . . ?
C16 C10 H10 106.6 . . ?
C12 C11 C10 110.4(9) . . ?
C12 C11 H11A 109.6 . . ?
C10 C11 H11A 109.6 . . ?
C12 C11 H11B 109.6 . . ?
C10 C11 H11B 109.6 . . ?
H11A C11 H11B 108.1 . . ?
C13 C12 C11 109.6(9) . . ?
C13 C12 H12A 109.8 . . ?
C11 C12 H12A 109.8 . . ?
C13 C12 H12B 109.8 . . ?
C11 C12 H12B 109.8 . . ?
H12A C12 H12B 108.2 . . ?
C12 C13 C14 113.7(10) . . ?
C12 C13 H13A 108.8 . . ?
C14 C13 H13A 108.8 . . ?
C12 C13 H13B 108.8 . . ?
C14 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
C15 C14 C13 113.3(8) . . ?
C15 C14 N9 113.4(6) . . ?
C13 C14 N9 109.3(8) . . ?
C15 C14 H14 106.8 . . ?
C13 C14 H14 106.8 . . ?
N9 C14 H14 106.8 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C10 C16 H16A 109.5 . . ?
C10 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C10 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C41 O8 H8 111.7 . . ?
O8 C41 C42 112.0(5) . . ?
O8 C41 H41A 109.2 . . ?
C42 C41 H41A 109.2 . . ?
O8 C41 H41B 109.2 . . ?
C42 C41 H41B 109.2 . . ?
H41A C41 H41B 107.9 . . ?
C41 C42 C43 116.2(5) . . ?
C41 C42 H42A 108.2 . . ?
C43 C42 H42A 108.2 . . ?
C41 C42 H42B 108.2 . . ?
C43 C42 H42B 108.2 . . ?
H42A C42 H42B 107.4 . . ?
C42 C43 H43A 109.5 . . ?
C42 C43 H43B 109.5 . . ?
H43A C43 H43B 109.5 . . ?
C42 C43 H43C 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
H1O7 O7 H2O7 111.0 . . ?

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
N9 Cu1 O3 C7 0.4(4) . . . . ?
N9 Cu1 O3 C7 -179.6(4) 2_666 . . . ?
C7 N8 N9 C10 -127.1(6) . . . . ?
C7 N8 N9 C14 110.0(7) . . . . ?
C7 N8 N9 Cu1 -3.2(6) . . . . ?
C6 C1 C2 C3 0.8(8) . . . . ?
C6 C1 C2 S1 -178.3(4) . . . . ?
O2 S1 C2 C3 -173.8(5) . . . . ?
O1 S1 C2 C3 62.5(5) . . . . ?
N1 S1 C2 C3 -56.4(5) . . . . ?
O2 S1 C2 C1 5.3(5) . . . . ?
O1 S1 C2 C1 -118.4(5) . . . . ?
N1 S1 C2 C1 122.7(4) . . . . ?
C1 C2 C3 C4 2.0(8) . . . . ?
S1 C2 C3 C4 -178.8(4) . . . . ?
C1 C2 C3 Cl1 -178.3(4) . . . . ?
S1 C2 C3 Cl1 0.8(7) . . . . ?
C2 C3 C4 C5 -3.0(10) . . . . ?
Cl1 C3 C4 C5 177.4(5) . . . . ?
C3 C4 C5 C6 0.8(9) . . . . ?
C4 C5 C6 C1 2.2(9) . . . . ?
C4 C5 C6 C7 -176.4(5) . . . . ?
C2 C1 C6 C5 -3.1(9) . . . . ?
C2 C1 C6 C7 175.3(5) . . . . ?
N9 N8 C7 O3 4.3(9) . . . . ?
N9 N8 C7 C6 -174.7(5) . . . . ?
Cu1 O3 C7 N8 -3.0(8) . . . . ?
Cu1 O3 C7 C6 176.0(4) . . . . ?
C5 C6 C7 N8 34.8(8) . . . . ?
C1 C6 C7 N8 -143.7(6) . . . . ?
C5 C6 C7 O3 -144.3(5) . . . . ?
C1 C6 C7 O3 37.2(8) . . . . ?
N8 N9 C10 C11 -74.8(9) . . . . ?
C14 N9 C10 C11 48.8(10) . . . . ?
Cu1 N9 C10 C11 164.5(7) . . . . ?
N8 N9 C10 C16 52.8(8) . . . . ?
C14 N9 C10 C16 176.5(6) . . . . ?
Cu1 N9 C10 C16 -67.9(7) . . . . ?
N9 C10 C11 C12 -51.1(12) . . . . ?
C16 C10 C11 C12 -176.9(9) . . . . ?
C10 C11 C12 C13 54.3(12) . . . . ?
C11 C12 C13 C14 -61.8(12) . . . . ?
C12 C13 C14 C15 -173.8(8) . . . . ?
C12 C13 C14 N9 58.6(10) . . . . ?
C10 N9 C14 C15 -178.9(6) . . . . ?
N8 N9 C14 C15 -59.1(8) . . . . ?
Cu1 N9 C14 C15 58.3(7) . . . . ?
C10 N9 C14 C13 -51.4(8) . . . . ?
N8 N9 C14 C13 68.4(8) . . . . ?
Cu1 N9 C14 C13 -174.2(6) . . . . ?
O8 C41 C42 C43 62.0(7) . . . . ?

_refine_diff_density_max         0.858
_refine_diff_density_min         -0.942
_refine_diff_density_rms         0.102

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC6
_database_code_depnum_ccdc_archive 'CCDC 2099754'
loop_
_audit_author_name
_audit_author_address
'Petra Bombicz'
;Centre for Structural Science, Research Centre for Natural Sciences
Hungary
;
_audit_update_record             
;
2021-07-27 deposited with the CCDC.	2021-08-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'trans-bis(4-chloro-N-(2,6-dimethylpiperidin-1-yl)-3-sulfamoylbenzamide)-copper(II) diisoprophanol solvate dihydrate'
_chemical_name_common            'clopamide copper(II) diisoprophanol dihydrate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H38 Cl2 Cu N6 O6 S2, 2(C3 H8 O), 2(H2 O)'
_chemical_formula_sum            'C34 H58 Cl2 Cu N6 O10 S2'
_chemical_formula_weight         909.42

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.3107(14)
_cell_length_b                   8.7469(14)
_cell_length_c                   16.387(3)
_cell_angle_alpha                79.713(5)
_cell_angle_beta                 87.099(4)
_cell_angle_gamma                65.629(4)
_cell_volume                     1067.3(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    24202
_cell_measurement_theta_min      3.01
_cell_measurement_theta_max      28.70

_exptl_crystal_description       Platelet
_exptl_crystal_colour            Brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'Not measured'
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_F_000             479
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.794
_shelx_estimated_absorpt_T_min   0.692
_shelx_estimated_absorpt_T_max   0.961
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.5771
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
;
 T.Higashi, Numerical Absorption Correction, NUMABS, 2002
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      103(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'NORMAL-focus sealed tube'
_diffrn_radiation_monochromator  Graphite
_diffrn_radiation_detector       RX
_diffrn_measurement_device_type  R-AXIS-RAPID
_diffrn_measurement_method       dtprofit.ref
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            51848
_diffrn_reflns_av_unetI/netI     0.0430
_diffrn_reflns_av_R_equivalents  0.0884
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.003
_diffrn_reflns_theta_max         28.698
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5523
_reflns_number_gt                4481
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Spek, A.L. (2003). J.Appl.Cryst. 36,7-13.'
_computing_publication_material  
;
MERCURY (Macrae et al., 2006); Platon (Spek, 2009)
;
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0395P)²+2.3848P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5523
_refine_ls_number_parameters     356
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0816
_refine_ls_R_factor_gt           0.0690
_refine_ls_wR_factor_ref         0.1574
_refine_ls_wR_factor_gt          0.1506
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
Cu1 Cu 0.5000 0.5000 0.5000 0.0498(2) Uani 1 2 d S . P C .
Cl1 Cl 0.46682(11) 0.19896(15) 0.03456(5) 0.0481(3) Uani 1 1 d . . . . .
S1 S 0.16563(10) 0.22867(11) 0.17407(5) 0.03207(19) Uani 1 1 d . . . . .
O3 O 0.4478(3) 0.4130(4) 0.41101(15) 0.0417(6) Uani 1 1 d . . . . .
O2 O 0.0550(3) 0.2769(3) 0.24302(14) 0.0388(6) Uani 1 1 d . . . . .
O1 O 0.2407(3) 0.0536(3) 0.16418(16) 0.0399(6) Uani 1 1 d . . . . .
N1 N 0.0528(4) 0.3378(4) 0.09178(18) 0.0346(6) Uani 1 1 d D . . . .
C2 C 0.3430(4) 0.2890(4) 0.18458(19) 0.0304(6) Uani 1 1 d . . . . .
C3 C 0.4732(4) 0.2721(5) 0.1250(2) 0.0362(7) Uani 1 1 d . . . . .
C1 C 0.3519(4) 0.3516(4) 0.25536(19) 0.0317(6) Uani 1 1 d . . . . .
H1 H 0.2655 0.3602 0.2966 0.038 Uiso 1 1 calc R U . . .
C5 C 0.6168(4) 0.3824(5) 0.2065(2) 0.0379(7) Uani 1 1 d . . . . .
H5 H 0.7121 0.4119 0.2146 0.045 Uiso 1 1 calc R U . . .
C4 C 0.6086(4) 0.3208(5) 0.1360(2) 0.0415(8) Uani 1 1 d . . . . .
H4 H 0.6954 0.3117 0.0949 0.050 Uiso 1 1 calc R U . . .
C7 C 0.4969(4) 0.4734(5) 0.3407(2) 0.0365(7) Uani 1 1 d . . . . .
C6 C 0.4871(4) 0.4022(4) 0.2664(2) 0.0334(7) Uani 1 1 d . . . . .
N8 N 0.5583(4) 0.5890(4) 0.3288(2) 0.0467(7) Uani 1 1 d . . . . .
N9 N 0.5813(5) 0.6354(6) 0.4087(3) 0.0643(11) Uani 1 1 d . . . . .
O8 O 0.8876(3) 0.6992(3) 0.08713(14) 0.0351(5) Uani 1 1 d . . . . .
H1O8 H 0.7868 0.7336 0.1077 0.042 Uiso 1 1 calc R U . A 1
O7 O 0.5778(3) 0.7731(4) 0.16667(17) 0.0430(6) Uani 1 1 d D . . . .
C43 C 1.1570(5) 0.7347(6) 0.0783(2) 0.0475(9) Uani 1 1 d . . . . .
H43A H 1.1167 0.8192 0.0273 0.071 Uiso 1 1 calc R U . B 1
H43B H 1.2177 0.6206 0.0641 0.071 Uiso 1 1 calc R U . B 1
H43C H 1.2385 0.7592 0.1095 0.071 Uiso 1 1 calc R U . B 1
C10A C 0.4931(12) 0.8099(9) 0.4176(4) 0.065(2) Uani 0.688(6) 1 d . . P C 1
H10A H 0.5070 0.8191 0.4766 0.079 Uiso 0.688(6) 1 calc R U P C 1
C11A C 0.5704(17) 0.9219(11) 0.3610(4) 0.098(4) Uani 0.688(6) 1 d . . P C 1
H11A H 0.5513 0.9188 0.3023 0.118 Uiso 0.688(6) 1 calc R U P C 1
H11B H 0.5079 1.0414 0.3697 0.118 Uiso 0.688(6) 1 calc R U P C 1
C12A C 0.7671(19) 0.8613(16) 0.3786(5) 0.114(5) Uani 0.688(6) 1 d . . P C 1
H12A H 0.8151 0.9300 0.3387 0.137 Uiso 0.688(6) 1 calc R U P C 1
H12B H 0.7860 0.8765 0.4352 0.137 Uiso 0.688(6) 1 calc R U P C 1
C13A C 0.8605(12) 0.6790(14) 0.3712(4) 0.088(3) Uani 0.688(6) 1 d . . P C 1
H13A H 0.9876 0.6394 0.3849 0.105 Uiso 0.688(6) 1 calc R U P C 1
H13B H 0.8496 0.6659 0.3132 0.105 Uiso 0.688(6) 1 calc R U P C 1
C14A C 0.7854(12) 0.5701(14) 0.4288(4) 0.0538(19) Uani 0.688(6) 1 d . . P C 1
H14A H 0.7985 0.5850 0.4868 0.065 Uiso 0.688(6) 1 calc R U P C 1
C15A C 0.8872(10) 0.3849(13) 0.4239(5) 0.057(2) Uani 0.688(6) 1 d . . P C 1
H15A H 1.0115 0.3500 0.4391 0.086 Uiso 0.688(6) 1 calc R U P C 1
H15B H 0.8785 0.3671 0.3672 0.086 Uiso 0.688(6) 1 calc R U P C 1
H15C H 0.8380 0.3167 0.4623 0.086 Uiso 0.688(6) 1 calc R U P C 1
C16A C 0.3021(16) 0.8622(12) 0.3989(6) 0.091(4) Uani 0.688(6) 1 d . . P C 1
H16A H 0.2579 0.7897 0.4374 0.137 Uiso 0.688(6) 1 calc R U P C 1
H16B H 0.2872 0.8499 0.3418 0.137 Uiso 0.688(6) 1 calc R U P C 1
H16C H 0.2356 0.9814 0.4052 0.137 Uiso 0.688(6) 1 calc R U P C 1
C41A C 0.9995(7) 0.7427(9) 0.1307(4) 0.0355(12) Uani 0.688(6) 1 d . . P C 1
H41A H 1.0418 0.6590 0.1835 0.043 Uiso 0.688(6) 1 calc R U P C 1
C42A C 0.9036(8) 0.9166(8) 0.1507(4) 0.0451(14) Uani 0.688(6) 1 d . . P C 1
H42A H 0.8003 0.9214 0.1836 0.068 Uiso 0.688(6) 1 calc R U P C 1
H42B H 0.8648 0.9997 0.0992 0.068 Uiso 0.688(6) 1 calc R U P C 1
H42C H 0.9823 0.9435 0.1826 0.068 Uiso 0.688(6) 1 calc R U P C 1
C10B C 0.4236(18) 0.8531(16) 0.3696(9) 0.039(3) Uani 0.312(6) 1 d . . P C 2
H10B H 0.4520 0.8878 0.3111 0.047 Uiso 0.312(6) 1 calc R U P C 2
C11B C 0.4489(17) 0.9654(16) 0.4235(7) 0.042(3) Uani 0.312(6) 1 d . . P C 2
H11C H 0.3605 1.0840 0.4070 0.050 Uiso 0.312(6) 1 calc R U P C 2
H11D H 0.4296 0.9259 0.4821 0.050 Uiso 0.312(6) 1 calc R U P C 2
C12B C 0.631(2) 0.9609(19) 0.4153(10) 0.056(4) Uani 0.312(6) 1 d . . P C 2
H12C H 0.6472 1.0327 0.4518 0.068 Uiso 0.312(6) 1 calc R U P C 2
H12D H 0.6503 1.0047 0.3573 0.068 Uiso 0.312(6) 1 calc R U P C 2
C13B C 0.7620(16) 0.7758(17) 0.4406(7) 0.044(3) Uani 0.312(6) 1 d . . P C 2
H13C H 0.7456 0.7361 0.4996 0.053 Uiso 0.312(6) 1 calc R U P C 2
H13D H 0.8839 0.7689 0.4351 0.053 Uiso 0.312(6) 1 calc R U P C 2
C14B C 0.7386(15) 0.6591(17) 0.3877(9) 0.038(3) Uani 0.312(6) 1 d . . P C 2
H14B H 0.7447 0.6986 0.3270 0.045 Uiso 0.312(6) 1 calc R U P C 2
C15B C 0.856(2) 0.477(2) 0.4145(10) 0.038(3) Uani 0.312(6) 1 d . . P C 2
H15D H 0.8320 0.4084 0.3794 0.057 Uiso 0.312(6) 1 calc R U P C 2
H15E H 0.8335 0.4407 0.4724 0.057 Uiso 0.312(6) 1 calc R U P C 2
H15F H 0.9794 0.4613 0.4092 0.057 Uiso 0.312(6) 1 calc R U P C 2
C16B C 0.2359(19) 0.8692(19) 0.3722(9) 0.043(3) Uani 0.312(6) 1 d . . P C 2
H16D H 0.1561 0.9861 0.3487 0.065 Uiso 0.312(6) 1 calc R U P C 2
H16E H 0.2051 0.8417 0.4298 0.065 Uiso 0.312(6) 1 calc R U P C 2
H16F H 0.2243 0.7901 0.3398 0.065 Uiso 0.312(6) 1 calc R U P C 2
C41B C 0.9578(16) 0.8292(17) 0.1033(8) 0.031(2) Uani 0.312(6) 1 d . . P C 2
H41B H 0.8956 0.9443 0.0686 0.038 Uiso 0.312(6) 1 calc R U P C 2
C42B C 0.950(2) 0.834(2) 0.1968(8) 0.046(3) Uani 0.312(6) 1 d . . P C 2
H42D H 1.0184 0.7192 0.2275 0.069 Uiso 0.312(6) 1 calc R U P C 2
H42E H 0.8271 0.8739 0.2140 0.069 Uiso 0.312(6) 1 calc R U P C 2
H42F H 1.0006 0.9115 0.2085 0.069 Uiso 0.312(6) 1 calc R U P C 2
H1O7 H 0.579(5) 0.722(4) 0.2155(11) 0.041(11) Uiso 1 1 d D . . . .
H2O7 H 0.485(6) 0.861(5) 0.160(2) 0.062(15) Uiso 1 1 d D . . . .
H1NB H 0.103(5) 0.304(5) 0.0439(15) 0.054(12) Uiso 1 1 d D . . . .
H1NA H 0.006(6) 0.434(6) 0.093(3) 0.046(13) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
Cu1 O3 1.904(2) 2_666 ?
Cu1 O3 1.904(2) . ?
Cu1 N9 2.006(4) 2_666 ?
Cu1 N9 2.006(4) . ?
Cl1 C3 1.727(3) . ?
S1 O2 1.430(2) . ?
S1 O1 1.432(3) . ?
S1 N1 1.594(3) . ?
S1 C2 1.784(3) . ?
O3 C7 1.299(4) . ?
C2 C1 1.385(4) . ?
C2 C3 1.400(4) . ?
C3 C4 1.387(5) . ?
C1 C6 1.397(4) . ?
C5 C4 1.375(5) . ?
C5 C6 1.399(4) . ?
C7 N8 1.291(5) . ?
C7 C6 1.482(5) . ?
N8 N9 1.483(5) . ?
N9 C14B 1.422(12) . ?
N9 C10A 1.426(8) . ?
N9 C14A 1.581(9) . ?
N9 C10B 1.828(14) . ?
O8 C41A 1.406(6) . ?
O8 C41B 1.542(11) . ?
C43 C41A 1.512(6) . ?
C43 C41B 1.585(12) . ?
C10A C16A 1.491(14) . ?
C10A C11A 1.539(11) . ?
C11A C12A 1.521(16) . ?
C12A C13A 1.482(15) . ?
C13A C14A 1.516(9) . ?
C14A C15A 1.501(12) . ?
C41A C42A 1.486(8) . ?
C10B C16B 1.507(19) . ?
C10B C11B 1.513(16) . ?
C11B C12B 1.500(19) . ?
C12B C13B 1.53(2) . ?
C13B C14B 1.527(16) . ?
C14B C15B 1.480(18) . ?
C41B C42B 1.537(17) . ?

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
O3 Cu1 O3 180.0 2_666 . ?
O3 Cu1 N9 83.38(12) 2_666 2_666 ?
O3 Cu1 N9 96.62(12) . 2_666 ?
O3 Cu1 N9 96.62(12) 2_666 . ?
O3 Cu1 N9 83.38(12) . . ?
N9 Cu1 N9 180.0 2_666 . ?
O2 S1 O1 118.95(16) . . ?
O2 S1 N1 107.46(16) . . ?
O1 S1 N1 107.44(17) . . ?
O2 S1 C2 105.61(14) . . ?
O1 S1 C2 107.81(15) . . ?
N1 S1 C2 109.33(15) . . ?
C7 O3 Cu1 111.2(2) . . ?
C1 C2 C3 119.7(3) . . ?
C1 C2 S1 118.0(2) . . ?
C3 C2 S1 122.3(2) . . ?
C4 C3 C2 120.2(3) . . ?
C4 C3 Cl1 118.0(2) . . ?
C2 C3 Cl1 121.8(3) . . ?
C2 C1 C6 120.4(3) . . ?
C4 C5 C6 121.0(3) . . ?
C5 C4 C3 119.8(3) . . ?
N8 C7 O3 126.1(3) . . ?
N8 C7 C6 115.6(3) . . ?
O3 C7 C6 118.3(3) . . ?
C1 C6 C5 118.9(3) . . ?
C1 C6 C7 121.4(3) . . ?
C5 C6 C7 119.8(3) . . ?
C7 N8 N9 110.6(3) . . ?
C14B N9 N8 96.1(6) . . ?
C10A N9 N8 117.9(5) . . ?
C10A N9 C14A 109.5(5) . . ?
N8 N9 C14A 109.1(4) . . ?
C14B N9 C10B 97.6(7) . . ?
N8 N9 C10B 88.3(5) . . ?
C14B N9 Cu1 137.4(7) . . ?
C10A N9 Cu1 107.2(4) . . ?
N8 N9 Cu1 108.5(2) . . ?
C14A N9 Cu1 103.7(4) . . ?
C10B N9 Cu1 116.8(4) . . ?
N9 C10A C16A 106.6(6) . . ?
N9 C10A C11A 111.6(7) . . ?
C16A C10A C11A 112.4(8) . . ?
C12A C11A C10A 111.4(7) . . ?
C13A C12A C11A 109.8(6) . . ?
C12A C13A C14A 111.4(8) . . ?
C15A C14A C13A 110.8(7) . . ?
C15A C14A N9 112.9(6) . . ?
C13A C14A N9 109.6(7) . . ?
O8 C41A C42A 110.5(5) . . ?
O8 C41A C43 109.1(4) . . ?
C42A C41A C43 110.0(5) . . ?
C16B C10B C11B 110.8(11) . . ?
C16B C10B N9 112.0(9) . . ?
C11B C10B N9 106.5(10) . . ?
C12B C11B C10B 110.9(11) . . ?
C11B C12B C13B 107.4(10) . . ?
C12B C13B C14B 112.1(11) . . ?
N9 C14B C15B 93.9(10) . . ?
N9 C14B C13B 110.5(9) . . ?
C15B C14B C13B 113.3(12) . . ?
C42B C41B O8 108.5(9) . . ?
C42B C41B C43 109.6(10) . . ?
O8 C41B C43 99.0(7) . . ?

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 S1 C2 C1 5.5(3) . . . . ?
O1 S1 C2 C1 -122.6(3) . . . . ?
N1 S1 C2 C1 120.9(3) . . . . ?
O2 S1 C2 C3 -175.7(3) . . . . ?
O1 S1 C2 C3 56.2(3) . . . . ?
N1 S1 C2 C3 -60.3(3) . . . . ?
C1 C2 C3 C4 -1.2(5) . . . . ?
S1 C2 C3 C4 180.0(3) . . . . ?
C1 C2 C3 Cl1 -178.6(3) . . . . ?
S1 C2 C3 Cl1 2.6(4) . . . . ?
C3 C2 C1 C6 1.8(5) . . . . ?
S1 C2 C1 C6 -179.4(3) . . . . ?
C6 C5 C4 C3 -2.2(6) . . . . ?
C2 C3 C4 C5 1.4(6) . . . . ?
Cl1 C3 C4 C5 178.9(3) . . . . ?
Cu1 O3 C7 N8 -6.1(5) . . . . ?
Cu1 O3 C7 C6 172.3(2) . . . . ?
C2 C1 C6 C5 -2.4(5) . . . . ?
C2 C1 C6 C7 178.5(3) . . . . ?
C4 C5 C6 C1 2.7(5) . . . . ?
C4 C5 C6 C7 -178.3(3) . . . . ?
N8 C7 C6 C1 -146.1(3) . . . . ?
O3 C7 C6 C1 35.3(5) . . . . ?
N8 C7 C6 C5 34.9(5) . . . . ?
O3 C7 C6 C5 -143.7(3) . . . . ?
O3 C7 N8 N9 5.1(5) . . . . ?
C6 C7 N8 N9 -173.4(3) . . . . ?
C7 N8 N9 C14B 143.4(6) . . . . ?
C7 N8 N9 C10A -123.4(5) . . . . ?
C7 N8 N9 C14A 111.0(5) . . . . ?
C7 N8 N9 C10B -119.1(5) . . . . ?
C7 N8 N9 Cu1 -1.4(4) . . . . ?
N8 N9 C10A C16A 55.2(7) . . . . ?
C14A N9 C10A C16A -179.3(6) . . . . ?
Cu1 N9 C10A C16A -67.4(7) . . . . ?
N8 N9 C10A C11A -67.8(7) . . . . ?
C14A N9 C10A C11A 57.6(7) . . . . ?
Cu1 N9 C10A C11A 169.5(5) . . . . ?
N9 C10A C11A C12A -57.8(8) . . . . ?
C16A C10A C11A C12A -177.5(7) . . . . ?
C10A C11A C12A C13A 55.2(9) . . . . ?
C11A C12A C13A C14A -56.9(8) . . . . ?
C12A C13A C14A C15A -177.1(7) . . . . ?
C12A C13A C14A N9 57.7(8) . . . . ?
C10A N9 C14A C15A 177.8(5) . . . . ?
N8 N9 C14A C15A -51.8(6) . . . . ?
Cu1 N9 C14A C15A 63.7(6) . . . . ?
C10A N9 C14A C13A -58.1(7) . . . . ?
N8 N9 C14A C13A 72.3(7) . . . . ?
Cu1 N9 C14A C13A -172.3(5) . . . . ?
C14B N9 C10B C16B 172.6(10) . . . . ?
N8 N9 C10B C16B 76.7(9) . . . . ?
Cu1 N9 C10B C16B -33.2(11) . . . . ?
C14B N9 C10B C11B -66.1(10) . . . . ?
N8 N9 C10B C11B -162.0(8) . . . . ?
Cu1 N9 C10B C11B 88.0(8) . . . . ?
C16B C10B C11B C12B -175.2(11) . . . . ?
N9 C10B C11B C12B 62.8(12) . . . . ?
C10B C11B C12B C13B -58.6(14) . . . . ?
C11B C12B C13B C14B 58.1(14) . . . . ?
N8 N9 C14B C15B -86.4(9) . . . . ?
C10B N9 C14B C15B -175.5(9) . . . . ?
Cu1 N9 C14B C15B 39.7(12) . . . . ?
N8 N9 C14B C13B 156.9(9) . . . . ?
C10B N9 C14B C13B 67.9(11) . . . . ?
Cu1 N9 C14B C13B -77.0(12) . . . . ?
C12B C13B C14B N9 -72.3(13) . . . . ?
C12B C13B C14B C15B -176.2(12) . . . . ?

_refine_diff_density_max         0.645
_refine_diff_density_min         -0.709
_refine_diff_density_rms         0.088

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC7
_database_code_depnum_ccdc_archive 'CCDC 2099751'
loop_
_audit_author_name
_audit_author_address
'Petra Bombicz'
;Centre for Structural Science, Research Centre for Natural Sciences
Hungary
;
_audit_update_record             
;
2021-07-27 deposited with the CCDC.	2021-08-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'trans-bis(4-chloro-N-(2,6-dimethylpiperidin-1-yl)-3-sulfamoylbenzamide)-copper(II) dimethanol solvate dihydrate'
_chemical_name_common            'clopamide copper(II) dimethanol dihydrate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H38 Cl2 Cu N6 O6 S2, 2(C H4 O), 2(H2 O)'
_chemical_formula_sum            'C30 H50 Cl2 Cu N6 O10 S2'
_chemical_formula_weight         853.32

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.7518(3)
_cell_length_b                   8.0901(4)
_cell_length_c                   16.3683(7)
_cell_angle_alpha                83.1130(10)
_cell_angle_beta                 78.8210(10)
_cell_angle_gamma                71.6590(10)
_cell_volume                     953.96(7)
_cell_formula_units_Z            1
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    25951
_cell_measurement_theta_min      3.02
_cell_measurement_theta_max      32.51

_exptl_crystal_description       prism
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'Not measured'
_exptl_crystal_density_diffrn    1.485
_exptl_crystal_F_000             447
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_exptl_absorpt_coefficient_mu    0.883
_shelx_estimated_absorpt_T_min   0.667
_shelx_estimated_absorpt_T_max   0.810
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.7746
_exptl_absorpt_correction_T_max  0.9182
_exptl_special_details           
;
 T.Higashi, Numerical Absorption Correction, NUMABS, 2002
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      103(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'NORMAL-focus sealed tube'
_diffrn_radiation_monochromator  Graphite
_diffrn_radiation_detector       RX
_diffrn_measurement_device_type  R-AXIS-RAPID
_diffrn_measurement_method       dtprofit.ref
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            41399
_diffrn_reflns_av_unetI/netI     0.0423
_diffrn_reflns_av_R_equivalents  0.0600
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.018
_diffrn_reflns_theta_max         32.525
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6813
_reflns_number_gt                5424
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2006)'
_computing_publication_material  
;
MERCURY (Macrae et al., 2006); Platon (Spek,
 2009
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0457P)²+1.1560P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6813
_refine_ls_number_parameters     235
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0684
_refine_ls_R_factor_gt           0.0472
_refine_ls_wR_factor_ref         0.1282
_refine_ls_wR_factor_gt          0.1020
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_restrained_S_all      1.105
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
Cu1 Cu 0.5000 0.5000 0.5000 0.01918(9) Uani 1 2 d S . P . .
Cl1 Cl 0.21945(8) 0.47878(7) 0.02102(3) 0.02539(12) Uani 1 1 d . . . . .
S1 S 0.21999(8) 0.16745(6) 0.16934(3) 0.02135(11) Uani 1 1 d . . . . .
O1 O 0.2598(3) 0.0553(2) 0.24229(10) 0.0296(4) Uani 1 1 d . . . . .
O2 O 0.0316(2) 0.2386(2) 0.15618(11) 0.0283(3) Uani 1 1 d . . . . .
O3 O 0.4223(2) 0.43976(19) 0.40637(9) 0.0213(3) Uani 1 1 d . . . . .
N1 N 0.3334(3) 0.0634(2) 0.08961(11) 0.0245(4) Uani 1 1 d D . . . .
H1NA H 0.2979 0.1078 0.0446 0.029 Uiso 1 1 d R U . . .
H1NB H 0.4352 0.0197 0.0923 0.029 Uiso 1 1 d DR U . . .
N8 N 0.6062(3) 0.6017(2) 0.32966(11) 0.0216(3) Uani 1 1 d . . . . .
N9 N 0.6410(3) 0.6267(2) 0.41159(11) 0.0208(3) Uani 1 1 d . . . . .
C1 C 0.3686(3) 0.3554(3) 0.24830(12) 0.0202(4) Uani 1 1 d . . . . .
H1 H 0.3756 0.2632 0.2905 0.024 Uiso 1 1 calc R U . . .
C2 C 0.3030(3) 0.3469(2) 0.17598(12) 0.0187(4) Uani 1 1 d . . . . .
C3 C 0.2942(3) 0.4827(3) 0.11354(12) 0.0197(4) Uani 1 1 d . . . . .
C4 C 0.3458(3) 0.6267(3) 0.12484(13) 0.0221(4) Uani 1 1 d . . . . .
H4 H 0.3381 0.7194 0.0828 0.027 Uiso 1 1 calc R U . . .
C5 C 0.4085(3) 0.6353(3) 0.19750(13) 0.0219(4) Uani 1 1 d . . . . .
H5 H 0.4412 0.7353 0.2055 0.026 Uiso 1 1 calc R U . . .
C6 C 0.4243(3) 0.4984(3) 0.25916(12) 0.0196(4) Uani 1 1 d . . . . .
C7 C 0.4896(3) 0.5122(3) 0.33746(12) 0.0198(4) Uani 1 1 d . . . . .
C10 C 0.5666(3) 0.8201(3) 0.42609(14) 0.0248(4) Uani 1 1 d . . . . .
H10 H 0.5829 0.8344 0.4837 0.030 Uiso 1 1 calc R U . . .
C11 C 0.6727(4) 0.9265(3) 0.36559(15) 0.0307(5) Uani 1 1 d . . . . .
H11A H 0.6566 0.9174 0.3079 0.037 Uiso 1 1 calc R U . . .
H11B H 0.6219 1.0509 0.3784 0.037 Uiso 1 1 calc R U . . .
C12 C 0.8775(4) 0.8633(4) 0.37114(16) 0.0337(5) Uani 1 1 d . . . . .
H12A H 0.9440 0.9289 0.3284 0.040 Uiso 1 1 calc R U . . .
H12B H 0.8955 0.8850 0.4267 0.040 Uiso 1 1 calc R U . . .
C13 C 0.9550(3) 0.6696(3) 0.35748(15) 0.0307(5) Uani 1 1 d . . . . .
H13A H 1.0843 0.6280 0.3673 0.037 Uiso 1 1 calc R U . . .
H13B H 0.9554 0.6515 0.2987 0.037 Uiso 1 1 calc R U . . .
C14 C 0.8449(3) 0.5613(3) 0.41484(14) 0.0258(4) Uani 1 1 d . . . . .
H14 H 0.8602 0.5699 0.4733 0.031 Uiso 1 1 calc R U . . .
C15 C 0.9216(4) 0.3683(3) 0.39598(16) 0.0326(5) Uani 1 1 d . . . . .
H15A H 0.8523 0.3011 0.4351 0.049 Uiso 1 1 calc R U . . .
H15B H 1.0519 0.3250 0.4021 0.049 Uiso 1 1 calc R U . . .
H15C H 0.9097 0.3554 0.3387 0.049 Uiso 1 1 calc R U . . .
C16 C 0.3620(3) 0.8859(3) 0.42314(15) 0.0269(4) Uani 1 1 d . . . . .
H16A H 0.3409 0.8702 0.3678 0.040 Uiso 1 1 calc R U . . .
H16B H 0.3151 1.0100 0.4341 0.040 Uiso 1 1 calc R U . . .
H16C H 0.2976 0.8200 0.4656 0.040 Uiso 1 1 calc R U . . .
O8 O 0.7207(2) 0.8981(2) 0.08185(10) 0.0274(3) Uani 1 1 d . . . . .
H1O8 H 0.7547 0.8006 0.1051 0.041 Uiso 1 1 d R U . . .
C41 C 0.8175(4) 1.0061(4) 0.10353(17) 0.0372(6) Uani 1 1 d . . . . .
H41C H 0.7906 1.1167 0.0696 0.056 Uiso 1 1 calc R U . . .
H41B H 0.9503 0.9465 0.0931 0.056 Uiso 1 1 calc R U . . .
H41A H 0.7781 1.0292 0.1627 0.056 Uiso 1 1 calc R U . . .
O7 O 0.8352(2) 0.6022(2) 0.17117(10) 0.0293(4) Uani 1 1 d . . . . .
H1O7 H 0.8932 0.5015 0.1628 0.044 Uiso 1 1 d R U . . .
H2O7 H 0.7685 0.5956 0.2164 0.044 Uiso 1 1 d R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
Cu1 O3 1.9161(14) . ?
Cu1 O3 1.9161(14) 2_666 ?
Cu1 N9 2.0186(18) . ?
Cu1 N9 2.0186(18) 2_666 ?
Cl1 C3 1.730(2) . ?
S1 O1 1.4320(17) . ?
S1 O2 1.4401(18) . ?
S1 N1 1.5930(18) . ?
S1 C2 1.785(2) . ?
O3 C7 1.301(2) . ?
N1 H1NA 0.8372 . ?
N1 H1NB 0.7641 . ?
N8 C7 1.305(3) . ?
N8 N9 1.467(2) . ?
N9 C14 1.510(3) . ?
N9 C10 1.519(3) . ?
C1 C2 1.393(3) . ?
C1 C6 1.397(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.402(3) . ?
C3 C4 1.388(3) . ?
C4 C5 1.386(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.398(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.494(3) . ?
C10 C16 1.514(3) . ?
C10 C11 1.525(3) . ?
C10 H10 1.0000 . ?
C11 C12 1.524(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.518(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.530(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.532(3) . ?
C14 H14 1.0000 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
O8 C41 1.430(3) . ?
O8 H1O8 0.8200 . ?
C41 H41C 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41A 0.9800 . ?
O7 H1O7 0.8111 . ?
O7 H2O7 0.8233 . ?

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
O3 Cu1 O3 180.0 . 2_666 ?
O3 Cu1 N9 83.49(7) . . ?
O3 Cu1 N9 96.51(7) 2_666 . ?
O3 Cu1 N9 96.51(7) . 2_666 ?
O3 Cu1 N9 83.49(7) 2_666 2_666 ?
N9 Cu1 N9 180.0 . 2_666 ?
O1 S1 O2 119.09(11) . . ?
O1 S1 N1 108.11(10) . . ?
O2 S1 N1 107.18(10) . . ?
O1 S1 C2 105.41(10) . . ?
O2 S1 C2 107.32(10) . . ?
N1 S1 C2 109.49(10) . . ?
C7 O3 Cu1 110.49(13) . . ?
S1 N1 H1NA 114.4 . . ?
S1 N1 H1NB 113.6 . . ?
H1NA N1 H1NB 122.0 . . ?
C7 N8 N9 110.78(16) . . ?
N8 N9 C14 110.52(16) . . ?
N8 N9 C10 108.16(16) . . ?
C14 N9 C10 110.17(16) . . ?
N8 N9 Cu1 108.60(12) . . ?
C14 N9 Cu1 111.21(13) . . ?
C10 N9 Cu1 108.08(13) . . ?
C2 C1 C6 120.47(18) . . ?
C2 C1 H1 119.8 . . ?
C6 C1 H1 119.8 . . ?
C1 C2 C3 119.56(18) . . ?
C1 C2 S1 118.00(15) . . ?
C3 C2 S1 122.33(15) . . ?
C4 C3 C2 120.14(18) . . ?
C4 C3 Cl1 117.68(15) . . ?
C2 C3 Cl1 122.19(15) . . ?
C5 C4 C3 119.95(19) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 120.70(19) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 119.12(19) . . ?
C1 C6 C7 121.15(18) . . ?
C5 C6 C7 119.62(18) . . ?
O3 C7 N8 126.42(19) . . ?
O3 C7 C6 117.94(18) . . ?
N8 C7 C6 115.61(18) . . ?
C16 C10 N9 110.29(18) . . ?
C16 C10 C11 111.9(2) . . ?
N9 C10 C11 112.18(18) . . ?
C16 C10 H10 107.4 . . ?
N9 C10 H10 107.4 . . ?
C11 C10 H10 107.4 . . ?
C12 C11 C10 111.5(2) . . ?
C12 C11 H11A 109.3 . . ?
C10 C11 H11A 109.3 . . ?
C12 C11 H11B 109.3 . . ?
C10 C11 H11B 109.3 . . ?
H11A C11 H11B 108.0 . . ?
C13 C12 C11 110.1(2) . . ?
C13 C12 H12A 109.6 . . ?
C11 C12 H12A 109.6 . . ?
C13 C12 H12B 109.6 . . ?
C11 C12 H12B 109.6 . . ?
H12A C12 H12B 108.2 . . ?
C12 C13 C14 112.8(2) . . ?
C12 C13 H13A 109.0 . . ?
C14 C13 H13A 109.0 . . ?
C12 C13 H13B 109.0 . . ?
C14 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
N9 C14 C13 113.36(19) . . ?
N9 C14 C15 110.08(19) . . ?
C13 C14 C15 111.07(19) . . ?
N9 C14 H14 107.4 . . ?
C13 C14 H14 107.4 . . ?
C15 C14 H14 107.4 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C10 C16 H16A 109.5 . . ?
C10 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C10 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C41 O8 H1O8 109.5 . . ?
O8 C41 H41C 109.5 . . ?
O8 C41 H41B 109.5 . . ?
H41C C41 H41B 109.5 . . ?
O8 C41 H41A 109.5 . . ?
H41C C41 H41A 109.5 . . ?
H41B C41 H41A 109.5 . . ?
H1O7 O7 H2O7 103.7 . . ?

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
C7 N8 N9 C14 124.86(19) . . . . ?
C7 N8 N9 C10 -114.46(19) . . . . ?
C7 N8 N9 Cu1 2.6(2) . . . . ?
C6 C1 C2 C3 0.4(3) . . . . ?
C6 C1 C2 S1 -175.92(16) . . . . ?
O1 S1 C2 C1 -6.0(2) . . . . ?
O2 S1 C2 C1 121.92(17) . . . . ?
N1 S1 C2 C1 -122.07(17) . . . . ?
O1 S1 C2 C3 177.76(17) . . . . ?
O2 S1 C2 C3 -54.3(2) . . . . ?
N1 S1 C2 C3 61.7(2) . . . . ?
C1 C2 C3 C4 -1.8(3) . . . . ?
S1 C2 C3 C4 174.41(16) . . . . ?
C1 C2 C3 Cl1 178.43(16) . . . . ?
S1 C2 C3 Cl1 -5.4(3) . . . . ?
C2 C3 C4 C5 0.9(3) . . . . ?
Cl1 C3 C4 C5 -179.32(17) . . . . ?
C3 C4 C5 C6 1.4(3) . . . . ?
C2 C1 C6 C5 1.8(3) . . . . ?
C2 C1 C6 C7 178.10(19) . . . . ?
C4 C5 C6 C1 -2.7(3) . . . . ?
C4 C5 C6 C7 -179.07(19) . . . . ?
Cu1 O3 C7 N8 5.4(3) . . . . ?
Cu1 O3 C7 C6 -172.36(14) . . . . ?
N9 N8 C7 O3 -5.5(3) . . . . ?
N9 N8 C7 C6 172.27(16) . . . . ?
C1 C6 C7 O3 -29.8(3) . . . . ?
C5 C6 C7 O3 146.5(2) . . . . ?
C1 C6 C7 N8 152.2(2) . . . . ?
C5 C6 C7 N8 -31.5(3) . . . . ?
N8 N9 C10 C16 59.3(2) . . . . ?
C14 N9 C10 C16 -179.82(18) . . . . ?
Cu1 N9 C10 C16 -58.13(19) . . . . ?
N8 N9 C10 C11 -66.2(2) . . . . ?
C14 N9 C10 C11 54.7(2) . . . . ?
Cu1 N9 C10 C11 176.37(15) . . . . ?
C16 C10 C11 C12 178.06(19) . . . . ?
N9 C10 C11 C12 -57.3(3) . . . . ?
C10 C11 C12 C13 55.1(3) . . . . ?
C11 C12 C13 C14 -52.7(3) . . . . ?
N8 N9 C14 C13 67.3(2) . . . . ?
C10 N9 C14 C13 -52.2(2) . . . . ?
Cu1 N9 C14 C13 -171.99(14) . . . . ?
N8 N9 C14 C15 -57.8(2) . . . . ?
C10 N9 C14 C15 -177.25(18) . . . . ?
Cu1 N9 C14 C15 62.9(2) . . . . ?
C12 C13 C14 N9 52.5(3) . . . . ?
C12 C13 C14 C15 177.1(2) . . . . ?

_refine_diff_density_max         0.831
_refine_diff_density_min         -0.888
_refine_diff_density_rms         0.126

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC8
_database_code_depnum_ccdc_archive 'CCDC 2099752'
loop_
_audit_author_name
_audit_author_address
'Petra Bombicz'
;Centre for Structural Science, Research Centre for Natural Sciences
Hungary
;
_audit_update_record             
;
2021-07-27 deposited with the CCDC.	2021-08-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'trans-bis(4-chloro-N-(2,6-dimethylpiperidin-1-yl)-3-sulfamoylbenzamide)-copper(II) diethanol solvate dihydrate'
_chemical_name_common            'clopamide copper(II) diethanol dihydrate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H38 Cl2 Cu N6 O6 S2, 2(C2 H6 O), 2(H2 O)'
_chemical_formula_sum            'C32 H54 Cl2 Cu N6 O10 S2'
_chemical_formula_weight         881.37

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.2195(7)
_cell_length_b                   8.2439(7)
_cell_length_c                   16.4822(14)
_cell_angle_alpha                85.598(2)
_cell_angle_beta                 78.212(2)
_cell_angle_gamma                68.273(2)
_cell_volume                     1015.62(15)
_cell_formula_units_Z            1
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    20890
_cell_measurement_theta_min      3.04
_cell_measurement_theta_max      27.50

_exptl_crystal_description       Prism
_exptl_crystal_colour            Brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'Not measured'
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_F_000             463
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.831
_shelx_estimated_absorpt_T_min   0.789
_shelx_estimated_absorpt_T_max   0.921
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.7534
_exptl_absorpt_correction_T_max  0.8767
_exptl_absorpt_process_details   
;
 T.Higashi, Numerical Absorption Correction, NUMABS, 2002
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      103(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'NORMAL-focus sealed tube'
_diffrn_radiation_monochromator  Graphite
_diffrn_radiation_detector       RX
_diffrn_measurement_device_type  R-AXIS-RAPID
_diffrn_measurement_method       dtprofit.ref
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            43872
_diffrn_reflns_av_unetI/netI     0.0442
_diffrn_reflns_av_R_equivalents  0.0918
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.035
_diffrn_reflns_theta_max         27.478
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4634
_reflns_number_gt                3687
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Spek, A.L. (2003). J.Appl.Cryst. 36,7-13.'
_computing_publication_material  
;
MERCURY (Macrae et al., 2006); Platon (Spek, 2009)
;
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1118P)²+3.8287P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.007(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4634
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1175
_refine_ls_R_factor_gt           0.0969
_refine_ls_wR_factor_ref         0.2553
_refine_ls_wR_factor_gt          0.2379
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.095
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
Cu1 Cu 0.5000 0.5000 0.5000 0.0459(4) Uani 1 2 d S . P . .
Cl1 Cl 0.2064(2) 0.45688(17) 0.03509(8) 0.0438(4) Uani 1 1 d . . . . .
S1 S 0.23373(19) 0.15175(15) 0.17671(7) 0.0360(4) Uani 1 1 d . . . . .
O1 O 0.2887(6) 0.0389(4) 0.2444(2) 0.0403(9) Uani 1 1 d . . . . .
O2 O 0.0479(6) 0.2235(5) 0.1716(2) 0.0433(9) Uani 1 1 d . . . . .
O3 O 0.4201(6) 0.4395(5) 0.4098(2) 0.0431(10) Uani 1 1 d . . . . .
N1 N 0.3406(6) 0.0463(5) 0.0925(3) 0.0364(10) Uani 1 1 d . . . . .
H1NA H 0.2970 0.0963 0.0476 0.044 Uiso 1 1 d R U . . .
H1NB H 0.4570 0.0028 0.0870 0.044 Uiso 1 1 d R U . . .
N8 N 0.5977(8) 0.5757(7) 0.3294(3) 0.0489(12) Uani 1 1 d . . . . .
N9 N 0.6360(8) 0.6036(7) 0.4107(4) 0.0569(14) Uani 1 1 d . . . . .
C1 C 0.3674(8) 0.3423(6) 0.2541(3) 0.0365(12) Uani 1 1 d . . . . .
H1 H 0.3799 0.2525 0.2947 0.044 Uiso 1 1 calc R U . . .
C2 C 0.3015(7) 0.3320(6) 0.1839(3) 0.0351(11) Uani 1 1 d . . . . .
C3 C 0.2828(8) 0.4639(7) 0.1249(3) 0.0358(12) Uani 1 1 d . . . . .
C4 C 0.3260(8) 0.6065(7) 0.1366(3) 0.0411(13) Uani 1 1 d . . . . .
H4 H 0.3105 0.6976 0.0967 0.049 Uiso 1 1 calc R U . . .
C5 C 0.3916(8) 0.6171(7) 0.2061(3) 0.0402(12) Uani 1 1 d . . . . .
H5 H 0.4209 0.7153 0.2137 0.048 Uiso 1 1 calc R U . . .
C6 C 0.4147(8) 0.4830(7) 0.2651(3) 0.0388(12) Uani 1 1 d . . . . .
C7 C 0.4835(8) 0.4983(7) 0.3404(3) 0.0403(13) Uani 1 1 d . . . . .
C10 C 0.5591(13) 0.8063(10) 0.4269(5) 0.068(2) Uani 1 1 d . . . . .
H10 H 0.5738 0.8236 0.4840 0.082 Uiso 1 1 calc R U . . .
C11 C 0.6636(15) 0.8963(13) 0.3682(5) 0.082(3) Uani 1 1 d . . . . .
H11B H 0.6159 1.0222 0.3817 0.099 Uiso 1 1 calc R U . . .
H11A H 0.6493 0.8847 0.3109 0.099 Uiso 1 1 calc R U . . .
C12 C 0.8583(16) 0.8207(16) 0.3725(7) 0.100(3) Uani 1 1 d . . . . .
H12A H 0.9236 0.8783 0.3304 0.120 Uiso 1 1 calc R U . . .
H12B H 0.8736 0.8456 0.4277 0.120 Uiso 1 1 calc R U . . .
C13 C 0.9372(15) 0.6283(18) 0.3581(6) 0.106(4) Uani 1 1 d . . . . .
H13A H 1.0603 0.5829 0.3689 0.127 Uiso 1 1 calc R U . . .
H13B H 0.9436 0.6049 0.2993 0.127 Uiso 1 1 calc R U . . .
C14 C 0.8273(13) 0.5298(12) 0.4142(6) 0.082(3) Uani 1 1 d . . . . .
H14 H 0.8391 0.5388 0.4728 0.099 Uiso 1 1 calc R U . . .
C15 C 0.8939(13) 0.3353(18) 0.3927(7) 0.124(5) Uani 1 1 d . . . . .
H15C H 0.8818 0.3228 0.3358 0.187 Uiso 1 1 calc R U . . .
H15A H 0.8229 0.2789 0.4311 0.187 Uiso 1 1 calc R U . . .
H15B H 1.0196 0.2798 0.3975 0.187 Uiso 1 1 calc R U . . .
C16 C 0.3743(14) 0.8834(9) 0.4254(4) 0.075(3) Uani 1 1 d . . . . .
H16A H 0.3543 0.8682 0.3703 0.113 Uiso 1 1 calc R U . . .
H16B H 0.3319 1.0083 0.4378 0.113 Uiso 1 1 calc R U . . .
H16C H 0.3088 0.8270 0.4669 0.113 Uiso 1 1 calc R U . . .
O8 O 0.7182(5) 0.8816(5) 0.0810(2) 0.0399(9) Uani 1 1 d . . . . .
H1O8 H 0.7495 0.7808 0.1016 0.060 Uiso 1 1 d R U . . .
C41 C 0.7832(9) 0.9879(8) 0.1202(4) 0.0466(14) Uani 1 1 d . . . . .
H41A H 0.9092 0.9227 0.1246 0.056 Uiso 1 1 calc R U . . .
H41B H 0.7123 1.0195 0.1767 0.056 Uiso 1 1 calc R U . . .
C42 C 0.7684(10) 1.1511(8) 0.0692(4) 0.0508(15) Uani 1 1 d . . . . .
H42B H 0.6470 1.2059 0.0581 0.076 Uiso 1 1 calc R U . . .
H42A H 0.8535 1.1205 0.0165 0.076 Uiso 1 1 calc R U . . .
H42C H 0.7950 1.2328 0.0997 0.076 Uiso 1 1 calc R U . . .
O7 O 0.8039(6) 0.5849(5) 0.1682(3) 0.0499(11) Uani 1 1 d . . . . .
H1O7 H 0.8712 0.4827 0.1545 0.075 Uiso 1 1 d R U . . .
H2O7 H 0.7427 0.5794 0.2151 0.075 Uiso 1 1 d R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
Cu1 O3 1.909(4) . ?
Cu1 O3 1.909(4) 2_666 ?
Cu1 N9 1.997(6) . ?
Cu1 N9 1.997(6) 2_666 ?
Cl1 C3 1.735(5) . ?
S1 O1 1.432(4) . ?
S1 O2 1.438(4) . ?
S1 N1 1.605(4) . ?
S1 C2 1.789(5) . ?
O3 C7 1.294(7) . ?
N1 H1NA 0.8929 . ?
N1 H1NB 0.8764 . ?
N8 C7 1.294(8) . ?
N8 N9 1.491(7) . ?
N9 C14 1.473(11) . ?
N9 C10 1.575(9) . ?
C1 C6 1.387(8) . ?
C1 C2 1.395(8) . ?
C1 H1 0.9500 . ?
C2 C3 1.388(7) . ?
C3 C4 1.385(8) . ?
C4 C5 1.382(8) . ?
C4 H4 0.9500 . ?
C5 C6 1.400(7) . ?
C5 H5 0.9500 . ?
C6 C7 1.497(8) . ?
C10 C16 1.418(12) . ?
C10 C11 1.499(11) . ?
C10 H10 1.0000 . ?
C11 C12 1.502(15) . ?
C11 H11B 0.9900 . ?
C11 H11A 0.9900 . ?
C12 C13 1.492(16) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.555(15) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.535(16) . ?
C14 H14 1.0000 . ?
C15 H15C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
O8 C41 1.430(7) . ?
O8 H1O8 0.8400 . ?
C41 C42 1.509(8) . ?
C41 H41A 0.9900 . ?
C41 H41B 0.9900 . ?
C42 H42B 0.9800 . ?
C42 H42A 0.9800 . ?
C42 H42C 0.9800 . ?
O7 H1O7 0.8362 . ?
O7 H2O7 0.8391 . ?

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
O3 Cu1 O3 180.0 . 2_666 ?
O3 Cu1 N9 83.5(2) . . ?
O3 Cu1 N9 96.5(2) 2_666 . ?
O3 Cu1 N9 96.5(2) . 2_666 ?
O3 Cu1 N9 83.5(2) 2_666 2_666 ?
N9 Cu1 N9 180.0 . 2_666 ?
O1 S1 O2 119.3(3) . . ?
O1 S1 N1 107.6(2) . . ?
O2 S1 N1 107.5(2) . . ?
O1 S1 C2 105.5(2) . . ?
O2 S1 C2 107.0(2) . . ?
N1 S1 C2 109.7(2) . . ?
C7 O3 Cu1 111.0(4) . . ?
S1 N1 H1NA 113.7 . . ?
S1 N1 H1NB 115.7 . . ?
H1NA N1 H1NB 116.6 . . ?
C7 N8 N9 110.0(5) . . ?
C14 N9 N8 113.3(6) . . ?
C14 N9 C10 110.4(6) . . ?
N8 N9 C10 107.5(5) . . ?
C14 N9 Cu1 110.1(5) . . ?
N8 N9 Cu1 108.7(4) . . ?
C10 N9 Cu1 106.6(5) . . ?
C6 C1 C2 120.4(5) . . ?
C6 C1 H1 119.8 . . ?
C2 C1 H1 119.8 . . ?
C3 C2 C1 119.6(5) . . ?
C3 C2 S1 122.6(4) . . ?
C1 C2 S1 117.7(4) . . ?
C4 C3 C2 120.1(5) . . ?
C4 C3 Cl1 117.9(4) . . ?
C2 C3 Cl1 122.0(4) . . ?
C5 C4 C3 120.4(5) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 119.9(5) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C5 119.4(5) . . ?
C1 C6 C7 121.5(5) . . ?
C5 C6 C7 119.0(5) . . ?
N8 C7 O3 126.5(5) . . ?
N8 C7 C6 115.7(5) . . ?
O3 C7 C6 117.8(5) . . ?
C16 C10 C11 111.4(8) . . ?
C16 C10 N9 112.6(6) . . ?
C11 C10 N9 111.3(7) . . ?
C16 C10 H10 107.1 . . ?
C11 C10 H10 107.1 . . ?
N9 C10 H10 107.1 . . ?
C10 C11 C12 111.7(8) . . ?
C10 C11 H11B 109.3 . . ?
C12 C11 H11B 109.3 . . ?
C10 C11 H11A 109.3 . . ?
C12 C11 H11A 109.3 . . ?
H11B C11 H11A 107.9 . . ?
C13 C12 C11 112.4(9) . . ?
C13 C12 H12A 109.1 . . ?
C11 C12 H12A 109.1 . . ?
C13 C12 H12B 109.1 . . ?
C11 C12 H12B 109.1 . . ?
H12A C12 H12B 107.9 . . ?
C12 C13 C14 112.5(8) . . ?
C12 C13 H13A 109.1 . . ?
C14 C13 H13A 109.1 . . ?
C12 C13 H13B 109.1 . . ?
C14 C13 H13B 109.1 . . ?
H13A C13 H13B 107.8 . . ?
N9 C14 C15 107.0(8) . . ?
N9 C14 C13 113.2(8) . . ?
C15 C14 C13 112.9(9) . . ?
N9 C14 H14 107.8 . . ?
C15 C14 H14 107.8 . . ?
C13 C14 H14 107.8 . . ?
C14 C15 H15C 109.5 . . ?
C14 C15 H15A 109.5 . . ?
H15C C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15C C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C10 C16 H16A 109.5 . . ?
C10 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C10 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C41 O8 H1O8 109.5 . . ?
O8 C41 C42 108.9(5) . . ?
O8 C41 H41A 109.9 . . ?
C42 C41 H41A 109.9 . . ?
O8 C41 H41B 109.9 . . ?
C42 C41 H41B 109.9 . . ?
H41A C41 H41B 108.3 . . ?
C41 C42 H42B 109.5 . . ?
C41 C42 H42A 109.5 . . ?
H42B C42 H42A 109.5 . . ?
C41 C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H1O7 O7 H2O7 107.0 . . ?

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
C7 N8 N9 C14 125.0(6) . . . . ?
C7 N8 N9 C10 -112.8(6) . . . . ?
C7 N8 N9 Cu1 2.2(6) . . . . ?
C6 C1 C2 C3 -0.2(8) . . . . ?
C6 C1 C2 S1 -177.1(4) . . . . ?
O1 S1 C2 C3 175.2(4) . . . . ?
O2 S1 C2 C3 -56.8(5) . . . . ?
N1 S1 C2 C3 59.6(5) . . . . ?
O1 S1 C2 C1 -8.0(5) . . . . ?
O2 S1 C2 C1 120.0(4) . . . . ?
N1 S1 C2 C1 -123.6(4) . . . . ?
C1 C2 C3 C4 -1.3(8) . . . . ?
S1 C2 C3 C4 175.5(4) . . . . ?
C1 C2 C3 Cl1 178.6(4) . . . . ?
S1 C2 C3 Cl1 -4.7(7) . . . . ?
C2 C3 C4 C5 1.4(9) . . . . ?
Cl1 C3 C4 C5 -178.5(4) . . . . ?
C3 C4 C5 C6 0.0(9) . . . . ?
C2 C1 C6 C5 1.6(9) . . . . ?
C2 C1 C6 C7 179.2(5) . . . . ?
C4 C5 C6 C1 -1.5(9) . . . . ?
C4 C5 C6 C7 -179.2(5) . . . . ?
N9 N8 C7 O3 -5.2(8) . . . . ?
N9 N8 C7 C6 172.3(5) . . . . ?
Cu1 O3 C7 N8 5.4(7) . . . . ?
Cu1 O3 C7 C6 -172.0(4) . . . . ?
C1 C6 C7 N8 148.2(6) . . . . ?
C5 C6 C7 N8 -34.2(8) . . . . ?
C1 C6 C7 O3 -34.0(8) . . . . ?
C5 C6 C7 O3 143.5(5) . . . . ?
C14 N9 C10 C16 -179.2(6) . . . . ?
N8 N9 C10 C16 56.8(8) . . . . ?
Cu1 N9 C10 C16 -59.6(7) . . . . ?
C14 N9 C10 C11 54.9(9) . . . . ?
N8 N9 C10 C11 -69.1(8) . . . . ?
Cu1 N9 C10 C11 174.5(6) . . . . ?
C16 C10 C11 C12 177.3(7) . . . . ?
N9 C10 C11 C12 -56.1(10) . . . . ?
C10 C11 C12 C13 55.2(11) . . . . ?
C11 C12 C13 C14 -51.3(12) . . . . ?
N8 N9 C14 C15 -56.1(9) . . . . ?
C10 N9 C14 C15 -176.7(7) . . . . ?
Cu1 N9 C14 C15 65.9(8) . . . . ?
N8 N9 C14 C13 69.0(9) . . . . ?
C10 N9 C14 C13 -51.6(9) . . . . ?
Cu1 N9 C14 C13 -169.1(6) . . . . ?
C12 C13 C14 N9 51.2(12) . . . . ?
C12 C13 C14 C15 173.0(9) . . . . ?

_refine_diff_density_max         1.579
_refine_diff_density_min         -1.036
_refine_diff_density_rms         0.119

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC9
_database_code_depnum_ccdc_archive 'CCDC 2099749'
loop_
_audit_author_name
_audit_author_address
'Petra Bombicz'
;Research Centre for Natural Sciences
Hungary
;
_audit_update_record             
;
2021-07-27 deposited with the CCDC.	2021-08-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
4-chloro-N-(2,6-dimethylpiperidin-1-yl)-3-sulfamoylbenzamide hemihydrate
;
_chemical_name_common            'Clopamide hemihydrate'
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C14 H20 Cl N3 O3 S), O'
_chemical_formula_sum            'C28 H40 Cl2 N6 O7 S2'
_chemical_formula_weight         707.68

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'
Cl Cl 0.1484 0.1585 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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.
;

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'

_cell_length_a                   14.5166(8)
_cell_length_b                   9.3747(7)
_cell_length_c                   24.7064(17)
_cell_angle_alpha                90
_cell_angle_beta                 100.965(2)
_cell_angle_gamma                90
_cell_volume                     3300.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    32344
_cell_measurement_theta_min      3.03
_cell_measurement_theta_max      27.60

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'Not measured'
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_F_000             1488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.377
_shelx_estimated_absorpt_T_min   0.834
_shelx_estimated_absorpt_T_max   0.963
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.8179
_exptl_absorpt_correction_T_max  0.9450
_exptl_absorpt_process_details   
;
NUMABS; Higashi, 2002
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      103(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'NORMAL-focus sealed tube'
_diffrn_radiation_monochromator  Graphite
_diffrn_radiation_detector       RX
_diffrn_measurement_device_type  R-AXIS-RAPID
_diffrn_measurement_method       dtprofit.ref
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            45688
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_av_R_equivalents  0.0564
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         3.028
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3762
_reflns_number_gt                3253
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Crystal Clear (Rigaku/MSC, 2005)'
_computing_cell_refinement       'Crystal Clear (Rigaku/MSC, 2005)'
_computing_data_reduction        'Crystal Clear (Rigaku/MSC, 2005)'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2006)'
_computing_publication_material  
;
MERCURY (Macrae et al., 2006); Platon (Spek,
 2009
;
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0495P)²+6.3890P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3762
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0438
_refine_ls_wR_factor_ref         0.1109
_refine_ls_wR_factor_gt          0.1063
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.39923(3) 0.11388(6) 0.47375(2) 0.02921(14) Uani 1 1 d . . . . .
S1 S 0.18411(3) 0.16987(5) 0.40682(2) 0.02011(13) Uani 1 1 d . . . . .
O1 O 0.10132(9) 0.16212(16) 0.36508(5) 0.0266(3) Uani 1 1 d . . . . .
O2 O 0.18540(10) 0.09923(15) 0.45856(5) 0.0253(3) Uani 1 1 d . . . . .
O3 O 0.34411(14) -0.0957(2) 0.20910(7) 0.0597(6) Uani 1 1 d . . . . .
N1 N 0.20822(12) 0.33446(17) 0.41977(6) 0.0229(3) Uani 1 1 d . . . . .
H2N1 H 0.2146 0.3865 0.3930 0.028 Uiso 1 1 d R U . . .
H1N1 H 0.2457 0.3485 0.4508 0.028 Uiso 1 1 d R U . . .
N8 N 0.23919(13) 0.0838(2) 0.20208(6) 0.0307(4) Uani 1 1 d . . . . .
H8 H 0.2156 0.1499 0.2193 0.037 Uiso 1 1 d R U . . .
N9 N 0.20970(11) 0.07117(18) 0.14434(6) 0.0211(3) Uani 1 1 d . . . . .
C1 C 0.25469(13) 0.0717(2) 0.31928(7) 0.0224(4) Uani 1 1 d . . . . .
H1 H 0.1929 0.0881 0.2993 0.027 Uiso 1 1 calc R U . . .
C2 C 0.27573(13) 0.0982(2) 0.37578(7) 0.0199(4) Uani 1 1 d . . . . .
C3 C 0.36686(14) 0.0731(2) 0.40457(7) 0.0220(4) Uani 1 1 d . . . . .
C4 C 0.43507(14) 0.0191(2) 0.37747(8) 0.0258(4) Uani 1 1 d . . . . .
H4 H 0.4964 0.0001 0.3975 0.031 Uiso 1 1 calc R U . . .
C5 C 0.41343(15) -0.0070(2) 0.32131(8) 0.0285(4) Uani 1 1 d . . . . .
H5 H 0.4599 -0.0442 0.3028 0.034 Uiso 1 1 calc R U . . .
C6 C 0.32353(15) 0.0212(2) 0.29185(7) 0.0265(4) Uani 1 1 d . . . . .
C7 C 0.30287(15) -0.0048(2) 0.23051(8) 0.0307(5) Uani 1 1 d . . . . .
C10 C 0.23465(14) 0.2064(2) 0.11928(8) 0.0257(4) Uani 1 1 d . . . . .
H10 H 0.2027 0.2871 0.1346 0.031 Uiso 1 1 calc R U . . .
C11 C 0.1999(2) 0.2006(3) 0.05732(9) 0.0490(7) Uani 1 1 d . . . . .
H11A H 0.2134 0.2928 0.0409 0.059 Uiso 1 1 calc R U . . .
H11B H 0.2344 0.1251 0.0415 0.059 Uiso 1 1 calc R U . . .
C12 C 0.0963(2) 0.1708(3) 0.04226(11) 0.0681(11) Uani 1 1 d . . . . .
H12A H 0.0780 0.1581 0.0019 0.082 Uiso 1 1 calc R U . . .
H12B H 0.0608 0.2530 0.0530 0.082 Uiso 1 1 calc R U . . .
C13 C 0.07210(18) 0.0384(3) 0.07105(13) 0.0607(10) Uani 1 1 d . . . . .
H13A H 0.1010 -0.0454 0.0565 0.073 Uiso 1 1 calc R U . . .
H13B H 0.0032 0.0248 0.0631 0.073 Uiso 1 1 calc R U . . .
C14 C 0.10626(15) 0.0473(3) 0.13294(11) 0.0374(5) Uani 1 1 d . . . . .
H14 H 0.0755 0.1310 0.1473 0.045 Uiso 1 1 calc R U . . .
C15 C 0.0825(2) -0.0857(3) 0.16245(18) 0.0696(11) Uani 1 1 d . . . . .
H15A H 0.0984 -0.0706 0.2024 0.104 Uiso 1 1 calc R U . . .
H15B H 0.1185 -0.1667 0.1524 0.104 Uiso 1 1 calc R U . . .
H15C H 0.0153 -0.1059 0.1517 0.104 Uiso 1 1 calc R U . . .
C16 C 0.34003(18) 0.2310(3) 0.13308(15) 0.0544(8) Uani 1 1 d . . . . .
H16A H 0.3725 0.1481 0.1214 0.082 Uiso 1 1 calc R U . . .
H16B H 0.3597 0.2443 0.1729 0.082 Uiso 1 1 calc R U . . .
H16C H 0.3558 0.3163 0.1138 0.082 Uiso 1 1 calc R U . . .
O7 O 0.0492(3) 0.1824(5) 0.23920(16) 0.0590(11) Uani 0.5 1 d . . P A -1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 C3 1.7271(18) . ?
S1 O1 1.4289(14) . ?
S1 O2 1.4365(13) . ?
S1 N1 1.6010(17) . ?
S1 C2 1.7880(19) . ?
O3 C7 1.219(3) . ?
N1 H2N1 0.8417 . ?
N1 H1N1 0.8627 . ?
N8 C7 1.338(3) . ?
N8 N9 1.414(2) . ?
N8 H8 0.8600 . ?
N9 C10 1.485(3) . ?
N9 C14 1.491(3) . ?
C1 C6 1.393(3) . ?
C1 C2 1.393(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.398(3) . ?
C3 C4 1.392(3) . ?
C4 C5 1.385(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.393(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.508(3) . ?
C10 C11 1.519(3) . ?
C10 C16 1.520(3) . ?
C10 H10 1.0000 . ?
C11 C12 1.505(5) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.505(5) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.517(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.517(4) . ?
C14 H14 1.0000 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

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
O1 S1 O2 119.06(8) . . ?
O1 S1 N1 108.37(9) . . ?
O2 S1 N1 107.53(8) . . ?
O1 S1 C2 105.27(8) . . ?
O2 S1 C2 108.87(8) . . ?
N1 S1 C2 107.20(8) . . ?
S1 N1 H2N1 117.0 . . ?
S1 N1 H1N1 113.7 . . ?
H2N1 N1 H1N1 117.8 . . ?
C7 N8 N9 121.60(16) . . ?
C7 N8 H8 119.2 . . ?
N9 N8 H8 119.2 . . ?
N8 N9 C10 107.35(15) . . ?
N8 N9 C14 107.69(16) . . ?
C10 N9 C14 111.46(16) . . ?
C6 C1 C2 120.49(18) . . ?
C6 C1 H1 119.8 . . ?
C2 C1 H1 119.8 . . ?
C1 C2 C3 119.06(17) . . ?
C1 C2 S1 117.23(14) . . ?
C3 C2 S1 123.66(13) . . ?
C4 C3 C2 120.50(16) . . ?
C4 C3 Cl1 118.17(15) . . ?
C2 C3 Cl1 121.29(14) . . ?
C5 C4 C3 119.98(18) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 120.08(18) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C5 119.85(17) . . ?
C1 C6 C7 121.34(18) . . ?
C5 C6 C7 118.81(18) . . ?
O3 C7 N8 123.62(19) . . ?
O3 C7 C6 121.94(19) . . ?
N8 C7 C6 114.38(17) . . ?
N9 C10 C11 109.21(18) . . ?
N9 C10 C16 110.53(17) . . ?
C11 C10 C16 111.0(2) . . ?
N9 C10 H10 108.7 . . ?
C11 C10 H10 108.7 . . ?
C16 C10 H10 108.7 . . ?
C12 C11 C10 112.4(2) . . ?
C12 C11 H11A 109.1 . . ?
C10 C11 H11A 109.1 . . ?
C12 C11 H11B 109.1 . . ?
C10 C11 H11B 109.1 . . ?
H11A C11 H11B 107.9 . . ?
C11 C12 C13 110.3(2) . . ?
C11 C12 H12A 109.6 . . ?
C13 C12 H12A 109.6 . . ?
C11 C12 H12B 109.6 . . ?
C13 C12 H12B 109.6 . . ?
H12A C12 H12B 108.1 . . ?
C12 C13 C14 111.7(2) . . ?
C12 C13 H13A 109.3 . . ?
C14 C13 H13A 109.3 . . ?
C12 C13 H13B 109.3 . . ?
C14 C13 H13B 109.3 . . ?
H13A C13 H13B 107.9 . . ?
N9 C14 C15 110.2(2) . . ?
N9 C14 C13 108.8(2) . . ?
C15 C14 C13 112.2(3) . . ?
N9 C14 H14 108.5 . . ?
C15 C14 H14 108.5 . . ?
C13 C14 H14 108.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C10 C16 H16A 109.5 . . ?
C10 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C10 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

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
C7 N8 N9 C10 -118.9(2) . . . . ?
C7 N8 N9 C14 121.0(2) . . . . ?
C6 C1 C2 C3 -0.2(3) . . . . ?
C6 C1 C2 S1 177.44(15) . . . . ?
O1 S1 C2 C1 9.20(17) . . . . ?
O2 S1 C2 C1 137.91(15) . . . . ?
N1 S1 C2 C1 -106.05(16) . . . . ?
O1 S1 C2 C3 -173.33(16) . . . . ?
O2 S1 C2 C3 -44.61(18) . . . . ?
N1 S1 C2 C3 71.43(17) . . . . ?
C1 C2 C3 C4 -1.6(3) . . . . ?
S1 C2 C3 C4 -178.98(15) . . . . ?
C1 C2 C3 Cl1 176.08(15) . . . . ?
S1 C2 C3 Cl1 -1.4(2) . . . . ?
C2 C3 C4 C5 1.5(3) . . . . ?
Cl1 C3 C4 C5 -176.17(16) . . . . ?
C3 C4 C5 C6 0.2(3) . . . . ?
C2 C1 C6 C5 1.9(3) . . . . ?
C2 C1 C6 C7 -178.49(19) . . . . ?
C4 C5 C6 C1 -1.9(3) . . . . ?
C4 C5 C6 C7 178.5(2) . . . . ?
N9 N8 C7 O3 4.7(4) . . . . ?
N9 N8 C7 C6 -178.07(18) . . . . ?
C1 C6 C7 O3 -150.5(2) . . . . ?
C5 C6 C7 O3 29.1(4) . . . . ?
C1 C6 C7 N8 32.2(3) . . . . ?
C5 C6 C7 N8 -148.1(2) . . . . ?
N8 N9 C10 C11 -177.21(17) . . . . ?
C14 N9 C10 C11 -59.5(2) . . . . ?
N8 N9 C10 C16 60.4(2) . . . . ?
C14 N9 C10 C16 178.05(19) . . . . ?
N9 C10 C11 C12 55.7(2) . . . . ?
C16 C10 C11 C12 177.9(2) . . . . ?
C10 C11 C12 C13 -53.4(3) . . . . ?
C11 C12 C13 C14 54.3(3) . . . . ?
N8 N9 C14 C15 -58.4(2) . . . . ?
C10 N9 C14 C15 -175.9(2) . . . . ?
N8 N9 C14 C13 178.11(19) . . . . ?
C10 N9 C14 C13 60.6(2) . . . . ?
C12 C13 C14 N9 -57.6(3) . . . . ?
C12 C13 C14 C15 -179.9(2) . . . . ?

_refine_diff_density_max         0.370
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.069

