# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2020

####################################################################### 
# 
# 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_IP-17
_database_code_depnum_ccdc_archive 'CCDC 1949317'
loop_
_audit_author_name
_audit_author_address
'Vladimir Chernyshev'
;Lomonosov Moscow State University
Russia
;
_audit_update_record             
;
2019-08-26 deposited with the CCDC.	2020-04-13 downloaded from the CCDC.
;
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point_gt       ?
_chemical_melting_point_lt       ?
_chemical_formula_moiety         'C26 H28 Cl Cu N4 O4 S2'
_chemical_formula_sum            'C26 H28 Cl Cu N4 O4 S2'
_chemical_formula_weight         623.64

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_preparation       ?

_cell_length_a                   15.8162(10)
_cell_length_b                   10.0508(5)
_cell_length_c                   17.7915(12)
_cell_angle_alpha                90
_cell_angle_beta                 94.782(5)
_cell_angle_gamma                90
_cell_volume                     2818.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_diffrn_ambient_temperature      295(2)

_refine_ls_R_factor_all          0.1479
_refine_ls_R_factor_gt           0.0470
_refine_ls_wR_factor_ref         0.0990
_refine_ls_wR_factor_gt          0.0858

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 0.25138(3) 0.62797(5) 0.30859(3) 0.05447(19) Uani 1 1 d . . . . .
CL1 Cl 0.26577(7) 0.51743(10) 0.20020(6) 0.0715(3) Uani 1 1 d . . . . .
S4A S 0.15145(6) 0.77810(10) 0.31757(5) 0.0567(3) Uani 1 1 d . . . . .
O1A O 0.12271(15) 0.8529(3) 0.05039(14) 0.0543(7) Uani 1 1 d . . . . .
C2A C 0.0749(2) 0.7633(4) 0.0935(2) 0.0450(10) Uani 1 1 d . . . . .
N3A N 0.11829(17) 0.7470(3) 0.16881(17) 0.0456(7) Uani 1 1 d . . . . .
H3A H 0.1590 0.6900 0.1731 0.055 Uiso 1 1 calc R U . . .
C4A C 0.1017(2) 0.8106(3) 0.2312(2) 0.0423(9) Uani 1 1 d . . . . .
N5A N 0.04186(16) 0.9049(3) 0.22552(16) 0.0464(8) Uani 1 1 d . . . . .
H5A H 0.0249 0.9402 0.2657 0.056 Uiso 1 1 calc R U . . .
C6A C 0.0050(2) 0.9485(3) 0.1509(2) 0.0457(10) Uani 1 1 d . . . . .
H6A H -0.0486 0.9953 0.1562 0.055 Uiso 1 1 calc R U . . .
C6AA C 0.0662(2) 1.0396(4) 0.1148(2) 0.0458(10) Uani 1 1 d . . . . .
C7A C 0.0715(3) 1.1744(5) 0.1310(2) 0.0648(12) Uani 1 1 d . . . . .
H7A H 0.0331 1.2126 0.1615 0.078 Uiso 1 1 calc R U . . .
C8A C 0.1330(4) 1.2525(5) 0.1026(3) 0.0808(14) Uani 1 1 d . . . . .
H8A H 0.1363 1.3428 0.1139 0.097 Uiso 1 1 calc R U . . .
C9A C 0.1893(3) 1.1960(6) 0.0576(3) 0.0843(15) Uani 1 1 d . . . . .
H9A H 0.2310 1.2484 0.0386 0.101 Uiso 1 1 calc R U . . .
C10A C 0.1848(3) 1.0638(5) 0.0404(3) 0.0660(12) Uani 1 1 d . . . . .
H10A H 0.2227 1.0263 0.0092 0.079 Uiso 1 1 calc R U . . .
C15A C 0.1236(2) 0.9864(4) 0.0699(2) 0.0488(10) Uani 1 1 d . . . . .
C11A C -0.0117(2) 0.8232(3) 0.1041(2) 0.0446(9) Uani 1 1 d . . . . .
H11A H -0.0387 0.8485 0.0546 0.054 Uiso 1 1 calc R U . . .
C12A C 0.0751(3) 0.6357(4) 0.0499(2) 0.0707(12) Uani 1 1 d . . . . .
H12A H 0.0442 0.5691 0.0749 0.106 Uiso 1 1 calc R U . . .
H12B H 0.0488 0.6498 0.0000 0.106 Uiso 1 1 calc R U . . .
H12C H 0.1326 0.6065 0.0470 0.106 Uiso 1 1 calc R U . . .
C13A C -0.0715(2) 0.7318(5) 0.1426(2) 0.0580(11) Uani 1 1 d . . . . .
C14A C -0.1601(2) 0.7804(4) 0.1506(3) 0.0889(15) Uani 1 1 d . . . . .
H14A H -0.1673 0.8668 0.1279 0.133 Uiso 1 1 calc R U . . .
H14B H -0.2001 0.7196 0.1258 0.133 Uiso 1 1 calc R U . . .
H14C H -0.1697 0.7860 0.2031 0.133 Uiso 1 1 calc R U . . .
O14A O -0.04912(18) 0.6254(3) 0.16722(19) 0.0829(10) Uani 1 1 d . . . . .
S4B S 0.33657(6) 0.58893(10) 0.41097(6) 0.0577(3) Uani 1 1 d . . . . .
O1B O 0.40907(16) 0.1569(2) 0.31290(13) 0.0551(7) Uani 1 1 d . . . . .
C2B C 0.4527(2) 0.2834(4) 0.31230(19) 0.0454(9) Uani 1 1 d . . . . .
N3B N 0.39657(17) 0.3900(3) 0.33124(16) 0.0489(8) Uani 1 1 d . . . . .
H3B H 0.3614 0.4190 0.2955 0.059 Uiso 1 1 calc R U . . .
C4B C 0.39390(19) 0.4476(3) 0.3985(2) 0.0404(9) Uani 1 1 d . . . . .
N5B N 0.43807(16) 0.3934(3) 0.45698(16) 0.0454(7) Uani 1 1 d . . . . .
H5B H 0.4374 0.4295 0.5008 0.054 Uiso 1 1 calc R U . . .
C6B C 0.4881(2) 0.2726(4) 0.44805(19) 0.0469(10) Uani 1 1 d . . . . .
H6B H 0.5328 0.2659 0.4895 0.056 Uiso 1 1 calc R U . . .
C6AB C 0.4295(2) 0.1541(4) 0.4496(2) 0.0459(10) Uani 1 1 d . . . . .
C7B C 0.4076(3) 0.0970(4) 0.5154(2) 0.0569(11) Uani 1 1 d . . . . .
H7B H 0.4324 0.1280 0.5613 0.068 Uiso 1 1 calc R U . . .
C8B C 0.3496(3) -0.0056(4) 0.5146(3) 0.0651(12) Uani 1 1 d . . . . .
H8B H 0.3350 -0.0427 0.5597 0.078 Uiso 1 1 calc R U . . .
C9B C 0.3138(3) -0.0520(4) 0.4476(3) 0.0701(12) Uani 1 1 d . . . . .
H9B H 0.2752 -0.1217 0.4473 0.084 Uiso 1 1 calc R U . . .
C10B C 0.3336(3) 0.0019(4) 0.3806(3) 0.0631(11) Uani 1 1 d . . . . .
H10B H 0.3086 -0.0308 0.3351 0.076 Uiso 1 1 calc R U . . .
C15B C 0.3914(2) 0.1059(4) 0.3814(2) 0.0499(10) Uani 1 1 d . . . . .
C11B C 0.5277(2) 0.2785(3) 0.37366(19) 0.0442(9) Uani 1 1 d . . . . .
H11B H 0.5586 0.1952 0.3676 0.053 Uiso 1 1 calc R U . . .
C12B C 0.4751(3) 0.2988(4) 0.2329(2) 0.0662(11) Uani 1 1 d . . . . .
H12D H 0.5046 0.3813 0.2278 0.099 Uiso 1 1 calc R U . . .
H12E H 0.5108 0.2263 0.2203 0.099 Uiso 1 1 calc R U . . .
H12F H 0.4242 0.2985 0.1995 0.099 Uiso 1 1 calc R U . . .
C13B C 0.5900(2) 0.3942(5) 0.3672(2) 0.0524(10) Uani 1 1 d . . . . .
C14B C 0.6719(3) 0.3633(4) 0.3369(4) 0.1038(19) Uani 1 1 d . . . . .
H14D H 0.6733 0.2708 0.3236 0.156 Uiso 1 1 calc R U . . .
H14E H 0.6781 0.4165 0.2929 0.156 Uiso 1 1 calc R U . . .
H14F H 0.7174 0.3824 0.3744 0.156 Uiso 1 1 calc R U . . .
O14B O 0.57444(17) 0.5046(3) 0.38747(17) 0.0710(8) Uani 1 1 d . . . . .


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 S4A 2.2006(11) . ?
CU1 S4B 2.2085(10) . ?
CU1 CL1 2.2536(11) . ?
S4A C4A 1.699(4) . ?
O1A C15A 1.386(4) . ?
O1A C2A 1.439(4) . ?
C2A N3A 1.462(4) . ?
C2A C12A 1.498(5) . ?
C2A C11A 1.522(4) . ?
N3A C4A 1.326(4) . ?
N3A H3A 0.8600 . ?
C4A N5A 1.337(4) . ?
N5A C6A 1.471(4) . ?
N5A H5A 0.8600 . ?
C6A C6AA 1.514(5) . ?
C6A C11A 1.521(5) . ?
C6A H6A 0.9800 . ?
C6AA C15A 1.368(5) . ?
C6AA C7A 1.386(5) . ?
C7A C8A 1.379(6) . ?
C7A H7A 0.9300 . ?
C8A C9A 1.368(6) . ?
C8A H8A 0.9300 . ?
C9A C10A 1.364(5) . ?
C9A H9A 0.9300 . ?
C10A C15A 1.380(5) . ?
C10A H10A 0.9300 . ?
C11A C13A 1.522(5) . ?
C11A H11A 0.9800 . ?
C12A H12A 0.9600 . ?
C12A H12B 0.9600 . ?
C12A H12C 0.9600 . ?
C13A O14A 1.197(4) . ?
C13A C14A 1.503(5) . ?
C14A H14A 0.9600 . ?
C14A H14B 0.9600 . ?
C14A H14C 0.9600 . ?
S4B C4B 1.710(3) . ?
O1B C15B 1.373(4) . ?
O1B C2B 1.447(4) . ?
C2B N3B 1.449(4) . ?
C2B C12B 1.493(5) . ?
C2B C11B 1.544(5) . ?
N3B C4B 1.333(4) . ?
N3B H3B 0.8600 . ?
C4B N5B 1.322(4) . ?
N5B C6B 1.466(4) . ?
N5B H5B 0.8600 . ?
C6B C6AB 1.512(5) . ?
C6B C11B 1.511(5) . ?
C6B H6B 0.9800 . ?
C6AB C7B 1.373(5) . ?
C6AB C15B 1.395(5) . ?
C7B C8B 1.380(5) . ?
C7B H7B 0.9300 . ?
C8B C9B 1.358(6) . ?
C8B H8B 0.9300 . ?
C9B C10B 1.370(6) . ?
C9B H9B 0.9300 . ?
C10B C15B 1.388(5) . ?
C10B H10B 0.9300 . ?
C11B C13B 1.535(5) . ?
C11B H11B 0.9800 . ?
C12B H12D 0.9600 . ?
C12B H12E 0.9600 . ?
C12B H12F 0.9600 . ?
C13B O14B 1.198(4) . ?
C13B C14B 1.478(5) . ?
C14B H14D 0.9600 . ?
C14B H14E 0.9600 . ?
C14B H14F 0.9600 . ?

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
S4A CU1 S4B 117.03(4) . . ?
S4A CU1 CL1 121.64(4) . . ?
S4B CU1 CL1 121.33(4) . . ?
C4A S4A CU1 110.33(14) . . ?
C15A O1A C2A 117.9(3) . . ?
O1A C2A N3A 109.3(3) . . ?
O1A C2A C12A 103.6(3) . . ?
N3A C2A C12A 110.9(3) . . ?
O1A C2A C11A 109.6(3) . . ?
N3A C2A C11A 106.9(3) . . ?
C12A C2A C11A 116.3(3) . . ?
C4A N3A C2A 127.0(3) . . ?
C4A N3A H3A 116.5 . . ?
C2A N3A H3A 116.5 . . ?
N3A C4A N5A 117.9(3) . . ?
N3A C4A S4A 123.7(3) . . ?
N5A C4A S4A 118.4(3) . . ?
C4A N5A C6A 120.3(3) . . ?
C4A N5A H5A 119.9 . . ?
C6A N5A H5A 119.9 . . ?
N5A C6A C6AA 110.1(3) . . ?
N5A C6A C11A 106.6(3) . . ?
C6AA C6A C11A 110.9(3) . . ?
N5A C6A H6A 109.8 . . ?
C6AA C6A H6A 109.8 . . ?
C11A C6A H6A 109.8 . . ?
C15A C6AA C7A 118.1(4) . . ?
C15A C6AA C6A 119.4(3) . . ?
C7A C6AA C6A 122.2(4) . . ?
C6AA C7A C8A 120.9(4) . . ?
C6AA C7A H7A 119.6 . . ?
C8A C7A H7A 119.6 . . ?
C9A C8A C7A 119.4(4) . . ?
C9A C8A H8A 120.3 . . ?
C7A C8A H8A 120.3 . . ?
C10A C9A C8A 120.8(4) . . ?
C10A C9A H9A 119.6 . . ?
C8A C9A H9A 119.6 . . ?
C9A C10A C15A 119.2(4) . . ?
C9A C10A H10A 120.4 . . ?
C15A C10A H10A 120.4 . . ?
C6AA C15A C10A 121.6(4) . . ?
C6AA C15A O1A 122.1(3) . . ?
C10A C15A O1A 116.3(4) . . ?
C2A C11A C13A 114.6(3) . . ?
C2A C11A C6A 106.2(3) . . ?
C13A C11A C6A 109.8(3) . . ?
C2A C11A H11A 108.7 . . ?
C13A C11A H11A 108.7 . . ?
C6A C11A H11A 108.7 . . ?
C2A C12A H12A 109.5 . . ?
C2A C12A H12B 109.5 . . ?
H12A C12A H12B 109.5 . . ?
C2A C12A H12C 109.5 . . ?
H12A C12A H12C 109.5 . . ?
H12B C12A H12C 109.5 . . ?
O14A C13A C14A 120.4(4) . . ?
O14A C13A C11A 121.9(4) . . ?
C14A C13A C11A 117.7(4) . . ?
C13A C14A H14A 109.5 . . ?
C13A C14A H14B 109.5 . . ?
H14A C14A H14B 109.5 . . ?
C13A C14A H14C 109.5 . . ?
H14A C14A H14C 109.5 . . ?
H14B C14A H14C 109.5 . . ?
C4B S4B CU1 109.51(12) . . ?
C15B O1B C2B 117.9(3) . . ?
O1B C2B N3B 110.2(3) . . ?
O1B C2B C12B 104.4(3) . . ?
N3B C2B C12B 110.0(3) . . ?
O1B C2B C11B 107.8(3) . . ?
N3B C2B C11B 107.9(3) . . ?
C12B C2B C11B 116.4(3) . . ?
C4B N3B C2B 126.6(3) . . ?
C4B N3B H3B 116.7 . . ?
C2B N3B H3B 116.7 . . ?
N5B C4B N3B 118.3(3) . . ?
N5B C4B S4B 119.4(3) . . ?
N3B C4B S4B 122.3(3) . . ?
C4B N5B C6B 120.7(3) . . ?
C4B N5B H5B 119.6 . . ?
C6B N5B H5B 119.6 . . ?
N5B C6B C6AB 108.2(3) . . ?
N5B C6B C11B 109.2(3) . . ?
C6AB C6B C11B 110.2(3) . . ?
N5B C6B H6B 109.7 . . ?
C6AB C6B H6B 109.7 . . ?
C11B C6B H6B 109.7 . . ?
C7B C6AB C15B 118.3(4) . . ?
C7B C6AB C6B 122.9(3) . . ?
C15B C6AB C6B 118.6(3) . . ?
C6AB C7B C8B 121.2(4) . . ?
C6AB C7B H7B 119.4 . . ?
C8B C7B H7B 119.4 . . ?
C9B C8B C7B 119.5(4) . . ?
C9B C8B H8B 120.2 . . ?
C7B C8B H8B 120.2 . . ?
C8B C9B C10B 121.3(4) . . ?
C8B C9B H9B 119.3 . . ?
C10B C9B H9B 119.3 . . ?
C9B C10B C15B 119.1(4) . . ?
C9B C10B H10B 120.4 . . ?
C15B C10B H10B 120.4 . . ?
O1B C15B C10B 117.1(4) . . ?
O1B C15B C6AB 122.5(4) . . ?
C10B C15B C6AB 120.5(4) . . ?
C6B C11B C13B 114.2(3) . . ?
C6B C11B C2B 105.7(3) . . ?
C13B C11B C2B 112.5(3) . . ?
C6B C11B H11B 108.0 . . ?
C13B C11B H11B 108.0 . . ?
C2B C11B H11B 108.0 . . ?
C2B C12B H12D 109.5 . . ?
C2B C12B H12E 109.5 . . ?
H12D C12B H12E 109.5 . . ?
C2B C12B H12F 109.5 . . ?
H12D C12B H12F 109.5 . . ?
H12E C12B H12F 109.5 . . ?
O14B C13B C14B 120.9(4) . . ?
O14B C13B C11B 122.0(3) . . ?
C14B C13B C11B 117.1(4) . . ?
C13B C14B H14D 109.5 . . ?
C13B C14B H14E 109.5 . . ?
H14D C14B H14E 109.5 . . ?
C13B C14B H14F 109.5 . . ?
H14D C14B H14F 109.5 . . ?
H14E C14B H14F 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
C15A O1A C2A N3A -71.1(4) . . . . ?
C15A O1A C2A C12A 170.6(3) . . . . ?
C15A O1A C2A C11A 45.7(4) . . . . ?
O1A C2A N3A C4A 97.2(4) . . . . ?
C12A C2A N3A C4A -149.1(3) . . . . ?
C11A C2A N3A C4A -21.4(5) . . . . ?
C2A N3A C4A N5A -3.5(5) . . . . ?
C2A N3A C4A S4A 175.9(3) . . . . ?
CU1 S4A C4A N3A 3.9(3) . . . . ?
CU1 S4A C4A N5A -176.6(2) . . . . ?
N3A C4A N5A C6A -8.4(4) . . . . ?
S4A C4A N5A C6A 172.1(2) . . . . ?
C4A N5A C6A C6AA -76.8(4) . . . . ?
C4A N5A C6A C11A 43.5(4) . . . . ?
N5A C6A C6AA C15A 90.7(4) . . . . ?
C11A C6A C6AA C15A -27.0(4) . . . . ?
N5A C6A C6AA C7A -83.3(4) . . . . ?
C11A C6A C6AA C7A 159.0(3) . . . . ?
C15A C6AA C7A C8A 0.0(5) . . . . ?
C6A C6AA C7A C8A 174.1(4) . . . . ?
C6AA C7A C8A C9A 0.2(6) . . . . ?
C7A C8A C9A C10A 0.3(7) . . . . ?
C8A C9A C10A C15A -1.0(6) . . . . ?
C7A C6AA C15A C10A -0.7(5) . . . . ?
C6A C6AA C15A C10A -175.0(3) . . . . ?
C7A C6AA C15A O1A -179.6(3) . . . . ?
C6A C6AA C15A O1A 6.1(5) . . . . ?
C9A C10A C15A C6AA 1.2(6) . . . . ?
C9A C10A C15A O1A -179.8(4) . . . . ?
C2A O1A C15A C6AA -16.0(4) . . . . ?
C2A O1A C15A C10A 165.1(3) . . . . ?
O1A C2A C11A C13A 174.5(3) . . . . ?
N3A C2A C11A C13A -67.1(4) . . . . ?
C12A C2A C11A C13A 57.4(4) . . . . ?
O1A C2A C11A C6A -64.1(3) . . . . ?
N3A C2A C11A C6A 54.3(4) . . . . ?
C12A C2A C11A C6A 178.8(3) . . . . ?
N5A C6A C11A C2A -65.6(3) . . . . ?
C6AA C6A C11A C2A 54.2(3) . . . . ?
N5A C6A C11A C13A 58.7(3) . . . . ?
C6AA C6A C11A C13A 178.5(3) . . . . ?
C2A C11A C13A O14A 5.1(5) . . . . ?
C6A C11A C13A O14A -114.2(4) . . . . ?
C2A C11A C13A C14A -176.1(3) . . . . ?
C6A C11A C13A C14A 64.5(4) . . . . ?
C15B O1B C2B N3B -71.3(3) . . . . ?
C15B O1B C2B C12B 170.6(3) . . . . ?
C15B O1B C2B C11B 46.3(4) . . . . ?
O1B C2B N3B C4B 99.0(4) . . . . ?
C12B C2B N3B C4B -146.4(4) . . . . ?
C11B C2B N3B C4B -18.5(5) . . . . ?
C2B N3B C4B N5B -9.5(5) . . . . ?
C2B N3B C4B S4B 169.8(3) . . . . ?
CU1 S4B C4B N5B -168.6(2) . . . . ?
CU1 S4B C4B N3B 12.2(3) . . . . ?
N3B C4B N5B C6B -0.4(5) . . . . ?
S4B C4B N5B C6B -179.7(2) . . . . ?
C4B N5B C6B C6AB -82.5(4) . . . . ?
C4B N5B C6B C11B 37.5(4) . . . . ?
N5B C6B C6AB C7B -83.3(4) . . . . ?
C11B C6B C6AB C7B 157.3(3) . . . . ?
N5B C6B C6AB C15B 92.3(4) . . . . ?
C11B C6B C6AB C15B -27.1(4) . . . . ?
C15B C6AB C7B C8B 0.0(5) . . . . ?
C6B C6AB C7B C8B 175.7(3) . . . . ?
C6AB C7B C8B C9B 0.6(6) . . . . ?
C7B C8B C9B C10B -0.6(6) . . . . ?
C8B C9B C10B C15B 0.0(6) . . . . ?
C2B O1B C15B C10B 165.8(3) . . . . ?
C2B O1B C15B C6AB -14.7(5) . . . . ?
C9B C10B C15B O1B -179.8(3) . . . . ?
C9B C10B C15B C6AB 0.6(6) . . . . ?
C7B C6AB C15B O1B 179.8(3) . . . . ?
C6B C6AB C15B O1B 4.0(5) . . . . ?
C7B C6AB C15B C10B -0.7(5) . . . . ?
C6B C6AB C15B C10B -176.5(3) . . . . ?
N5B C6B C11B C13B 62.4(3) . . . . ?
C6AB C6B C11B C13B -178.8(3) . . . . ?
N5B C6B C11B C2B -61.9(3) . . . . ?
C6AB C6B C11B C2B 57.0(4) . . . . ?
O1B C2B C11B C6B -67.1(4) . . . . ?
N3B C2B C11B C6B 51.9(4) . . . . ?
C12B C2B C11B C6B 176.1(3) . . . . ?
O1B C2B C11B C13B 167.6(3) . . . . ?
N3B C2B C11B C13B -73.4(4) . . . . ?
C12B C2B C11B C13B 50.8(5) . . . . ?
C6B C11B C13B O14B -44.2(5) . . . . ?
C2B C11B C13B O14B 76.4(4) . . . . ?
C6B C11B C13B C14B 134.0(4) . . . . ?
C2B C11B C13B C14B -105.4(4) . . . . ?


loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A

N3A H3A Cl1 0.86 2.44 3.295(3) 172 .
N3B H3B Cl1 0.86 2.39 3.248(3) 175 .
N5A H5A O14A 0.86 2.23 2.921(4) 138 2_555
N5B H5B O14B 0.86 2.12 2.973(4) 172 3_666


#########################################################################

_audit_creation_method           SHELXL-2015/1
_shelx_SHELXL_version_number     2015/1

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
Cu Cu -1.9646 0.5888 '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'

_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.
;

_cell_measurement_reflns_used    23672
_cell_measurement_theta_min      4.989
_cell_measurement_theta_max      72.832

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1288
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.09
_exptl_absorpt_coefficient_mu    3.678
_shelx_estimated_absorpt_T_min   0.527
_shelx_estimated_absorpt_T_max   0.527
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_factor_muR        0.184
_exptl_absorpt_process_details   
;
Walker, N. & Stuart, D (1983) Acta. Cryst. A39, 158-166
;
_exptl_absorpt_correction_T_min  0.6880
_exptl_absorpt_correction_T_max  0.6923

_diffrn_radiation_wavelength     1.5418
_diffrn_detector                 Pilatus100K
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 5.81
_diffrn_source                   'Cu GeniX 3D'
_diffrn_source_voltage           50
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_monochromator  none
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_measurement_method       'rotation method'
_diffrn_measurement_details      
'65 runs, 1721 frames, detector distance = 42 mm'
_diffrn_measurement_device_type  'Stoe STADI VARI'
_diffrn_reflns_number            23672
_diffrn_reflns_av_unetI/netI     0.1939
_diffrn_reflns_av_R_equivalents  0.0617 #before absorption correction
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         4.989
_diffrn_reflns_theta_max         72.832
_diffrn_reflns_theta_full        67.686
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             5497
_reflns_number_gt                2299
_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       'X--AREA       (STOE & CIE, 2015)'
_computing_cell_refinement       'X--AREA       (STOE & CIE, 2015)'
_computing_data_reduction        'X--AREA       (STOE & CIE, 2015)'
_computing_structure_solution    'SHELXS97      (Sheldrick,  2008)'
_computing_structure_refinement  'SHELXL-2015/1 (Sheldrick,  2015)'
_computing_molecular_graphics    'Ortep--3      (Farrugia,   1997)'
_computing_publication_material  'WinGX         (Farrugia,   1999)'

_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)+(0.0397P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5497
_refine_ls_number_parameters     343
_refine_ls_number_restraints     0
_refine_ls_goodness_of_fit_ref   0.744
_refine_ls_restrained_S_all      0.744
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

_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.
;

_refine_diff_density_max         0.258
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.063

####################################################################### 
# 
# 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_IP-19
_database_code_depnum_ccdc_archive 'CCDC 1949327'
loop_
_audit_author_name
_audit_author_address
'Vladimir Chernyshev'
;Lomonosov Moscow State University
Russia
;
_audit_update_record             
;
2019-08-26 deposited with the CCDC.	2020-04-13 downloaded from the CCDC.
;

_audit_creation_method           'MRIA, SHELXL-97'
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H28 Cl2 N4 O4 Pd S2'
_chemical_formula_sum            'C26 H28 Cl2 N4 O4 Pd S2'
_chemical_formula_weight         701.94

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Pd Pd 0.1215 3.9337 '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'
S S 0.3331 0.5567 '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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  'P 21/n'

loop_
_symmetry_equiv_pos_as_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                   9.3909(8)
_cell_length_b                   19.3472(17)
_cell_length_c                   8.1182(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.842(11)
_cell_angle_gamma                90.00
_cell_volume                     1432.1(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    869
_cell_measurement_theta_min      4.567
_cell_measurement_theta_max      39.988

_exptl_crystal_description       'no specific habit'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.628
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             712
_exptl_absorpt_coefficient_mu    8.642
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

#The next three fields give the specimen dimensions in mm.  The equatorial 
# plane contains the incident and diffracted beam.
_pd_spec_size_axial              15 # perpendicular to 
# equatorial plane

_pd_spec_size_equat              1 # parallel to 
# scattering vector 
# in transmission

_pd_spec_size_thick              1 # parallel to 
# scattering vector 
# in reflection

# The next five fields are character fields that describe the specimen.

_pd_spec_mounting                
; 
thin layer on the non-diffracting silicon plate
;
_pd_spec_mount_mode              reflection # options are 'reflection' 
# or 'transmission'

_pd_spec_shape                   flat_sheet # options are 'cylinder',
# 'flat_sheet' or 'irregular'

_pd_char_particle_morphology     'no specific habit'
_pd_char_colour                  brown # use ICDD colour descriptions

# The following three fields describe the preparation of the specimen. 
# The cooling rate is in K/min.  The pressure at which the sample was
# prepared is in kPa.  The temperature of preparation is in K.



_pd_prep_cool_rate               ?
_pd_prep_pressure                101
_pd_prep_temperature             295(2)


_exptl_special_details           
; 
 ? 
;

# This following item is used to identify the equipment used to record the
# powder pattern when the diffractogram was measured at a laboratory
# other than the authors' home institution, e.g. when neutron or synchrotron
# radiation is used.

_pd_instr_location               
;
 A. N. Frumkin Institute of Physical Chemistry and Electrochemistry RAS,
 Leninsky prospect, 31,
 Moscow 119071, 
 Russian Federation
;

_diffrn_ambient_temperature      295(2)
_diffrn_source                   'Fine focus X-ray tube'
_diffrn_source_target            Cu

_diffrn_radiation_source         'line-focus sealed tube'
_diffrn_radiation_monochromator  Ni-filter
_diffrn_measurement_device       'EMPYREAN (PANanalytical)'
_diffrn_detector_type            Xcelerator



_diffrn_reflns_number            ?
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_limit_l_max       ?


_pd_meas_scan_method             cont # options are 'step', 'cont',
# 'tof', 'fixed' or
# 'disp' (= dispersive)
_pd_meas_special_details         
; ?
;
# The following six items are used for angular dispersive measurements only.

_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418

# The following four items give details of the measured (not processed)
# powder pattern.  Angles are in degrees.

_pd_meas_number_of_points        4413
_pd_meas_2theta_range_min        5.008
_pd_meas_2theta_range_max        80.007
_pd_meas_2theta_range_inc        0.017

# The following three items are used for time-of-flight measurements only.

_pd_instr_dist_src/spec          ?
_pd_instr_dist_spec/detc         ?
_pd_meas_2theta_fixed            ?

# The following fields are used to identify the programs used.

_computing_data_collection       'DataCollector (PANalytical, 2010)'
_computing_cell_refinement       'MRIA (Zlokazov & Chernyshev, 1992)'
_computing_data_reduction        DataCollector
_computing_structure_solution    'simulated annealing (Zhukov et al., 2001)'
_computing_structure_refinement  MRIA
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'MRIA, SHELXL97 (Sheldrick, 2008)'

#==============================================================================

# 8. REFINEMENT DATA

# Use the next field to give any special details about the fitting of the
# powder pattern.

_pd_proc_ls_special_details      
; ?
;

# The next three items are given as text
_pd_proc_ls_profile_function     'split-type pseudo-Voigt (Toraya, 1986)'
_pd_proc_ls_pref_orient_corr     none
_pd_proc_ls_background_function  'Chebyshev polynomial up to the 5th order'

_pd_proc_ls_prof_R_factor        0.0337
_pd_proc_ls_prof_wR_factor       0.0434
_pd_proc_ls_prof_wR_expected     0.0250

_refine_special_details          
;
Anisotropic line broadening has been taken into account
(N.Popa, 1993)
;

_refine_ls_R_I_factor            0.0683
_refine_ls_structure_factor_coef Inet
_refine_ls_matrix_type           fullcycle
_refine_ls_weighting_scheme      sigma
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_parameters     107
_refine_ls_number_restraints     67
_refine_ls_number_constraints    0

# The following item is the same as CHI, the square root of 'CHI squared=3.010'
_refine_ls_goodness_of_fit_all   1.735

_refine_ls_restrained_S_all      ?
_refine_ls_restrained_S_obs      ?
_refine_ls_shift/su_max          .003
_refine_ls_shift/su_mean         .000


# The following four items apply to angular dispersive measurements.
# 2theta minimum, maximum and increment (in degrees) are for the 
# intensities used in the refinement.
_pd_proc_2theta_range_min        5.008
_pd_proc_2theta_range_max        80.007
_pd_proc_2theta_range_inc        0.017

_pd_proc_wavelength              1.5418

_pd_block_diffractogram_id       IP-19_pattern # The id used for the block
# containing the powder 
# pattern profile (section 11).

# Give appropriate details in the next two text fields.
_pd_proc_info_excluded_regions   none
_pd_proc_info_data_reduction     ?

#==============================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS


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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Pd1 Pd 0.5000 0.5000 0.5000 0.0490(7) Uiso 1 2 d S . .
Cl1 Cl 0.4791(4) 0.3916(2) 0.6157(4) 0.0630(17) Uiso 1 1 d . . .
S1 S 0.4626(4) 0.54490(19) 0.7529(4) 0.0460(15) Uiso 1 1 d . . .
O1 O 0.9237(9) 0.6621(4) 0.8626(9) 0.060(4) Uiso 1 1 d . . .
O2 O 0.5129(8) 0.7562(4) 0.8854(9) 0.059(4) Uiso 1 1 d . . .
C2 C 0.7779(13) 0.6900(6) 0.8271(14) 0.065(6) Uiso 1 1 d . . .
N3 N 0.6735(10) 0.6351(6) 0.7670(12) 0.058(4) Uiso 1 1 d . . .
H3 H 0.6657 0.6209 0.6648 0.070 Uiso 1 1 calc . . .
C4 C 0.5887(14) 0.6046(7) 0.8546(14) 0.065(6) Uiso 1 1 d . . .
N5 N 0.6160(11) 0.6182(5) 1.0193(11) 0.061(4) Uiso 1 1 d . . .
H5 H 0.5566 0.6036 1.0774 0.073 Uiso 1 1 calc . . .
C6 C 0.7444(14) 0.6573(7) 1.1024(14) 0.064(6) Uiso 1 1 d . . .
H6 H 0.7345 0.6728 1.2140 0.077 Uiso 1 1 calc . . .
C6A C 0.8829(13) 0.6158(7) 1.1215(14) 0.061(6) Uiso 1 1 d . . .
C7 C 0.9314(13) 0.5732(6) 1.2617(15) 0.067(6) Uiso 1 1 d . . .
H7 H 0.8771 0.5686 1.3430 0.080 Uiso 1 1 calc . . .
C8 C 1.0636(14) 0.5373(6) 1.2782(14) 0.064(6) Uiso 1 1 d . . .
H8 H 1.0954 0.5068 1.3680 0.077 Uiso 1 1 calc . . .
C9 C 1.1457(13) 0.5472(6) 1.1619(14) 0.062(6) Uiso 1 1 d . . .
H9 H 1.2361 0.5253 1.1773 0.075 Uiso 1 1 calc . . .
C10 C 1.0984(14) 0.5880(6) 1.0262(15) 0.061(6) Uiso 1 1 d . . .
H10 H 1.1536 0.5927 0.9458 0.073 Uiso 1 1 calc . . .
C10A C 0.9677(13) 0.6228(7) 1.0068(14) 0.065(6) Uiso 1 1 d . . .
C11 C 0.7483(13) 0.7195(6) 0.9894(15) 0.066(6) Uiso 1 1 d . . .
H11 H 0.8373 0.7449 1.0440 0.079 Uiso 1 1 calc . . .
C12 C 0.7722(13) 0.7367(6) 0.6768(14) 0.060(6) Uiso 1 1 d . . .
H12A H 0.6772 0.7579 0.6437 0.090 Uiso 1 1 calc . . .
H12B H 0.7898 0.7100 0.5840 0.090 Uiso 1 1 calc . . .
H12C H 0.8460 0.7719 0.7071 0.090 Uiso 1 1 calc . . .
C13 C 0.6264(13) 0.7675(6) 0.9869(14) 0.057(6) Uiso 1 1 d . . .
C14 C 0.6448(14) 0.8247(6) 1.1072(14) 0.061(6) Uiso 1 1 d . . .
H14A H 0.5554 0.8508 1.0884 0.091 Uiso 1 1 calc . . .
H14B H 0.7228 0.8541 1.0916 0.091 Uiso 1 1 calc . . .
H14C H 0.6683 0.8068 1.2208 0.091 Uiso 1 1 calc . . .

_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
Pd1 Cl1 2.325(4) . ?
Pd1 Cl1 2.325(4) 3_666 ?
Pd1 S1 2.332(4) 3_666 ?
Pd1 S1 2.332(4) . ?
S1 C4 1.718(13) . ?
O1 C10A 1.374(14) . ?
O1 C2 1.435(14) . ?
O2 C13 1.201(13) . ?
C2 N3 1.449(15) . ?
C2 C12 1.508(17) . ?
C2 C11 1.522(18) . ?
N3 C4 1.326(17) . ?
N3 H3 0.8598 . ?
C4 N5 1.326(15) . ?
N5 C6 1.447(15) . ?
N5 H5 0.8602 . ?
C6 C6A 1.504(18) . ?
C6 C11 1.518(18) . ?
C6 H6 0.9803 . ?
C6A C10A 1.369(19) . ?
C6A C7 1.391(16) . ?
C7 C8 1.401(18) . ?
C7 H7 0.9303 . ?
C8 C9 1.368(19) . ?
C8 H8 0.9301 . ?
C9 C10 1.341(16) . ?
C9 H9 0.9301 . ?
C10 C10A 1.376(18) . ?
C10 H10 0.9298 . ?
C11 C13 1.471(18) . ?
C11 H11 0.9802 . ?
C12 H12A 0.9603 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.458(17) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9602 . ?
C14 H14C 0.9598 . ?

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
Cl1 Pd1 Cl1 180.00(8) . 3_666 ?
Cl1 Pd1 S1 93.71(13) . 3_666 ?
Cl1 Pd1 S1 86.29(13) 3_666 3_666 ?
Cl1 Pd1 S1 86.29(13) . . ?
Cl1 Pd1 S1 93.71(13) 3_666 . ?
S1 Pd1 S1 180.00(7) 3_666 . ?
C4 S1 Pd1 116.2(5) . . ?
C10A O1 C2 117.2(9) . . ?
O1 C2 N3 109.2(9) . . ?
O1 C2 C12 103.6(10) . . ?
N3 C2 C12 106.1(9) . . ?
O1 C2 C11 109.3(8) . . ?
N3 C2 C11 108.5(10) . . ?
C12 C2 C11 119.8(10) . . ?
C4 N3 C2 126.2(10) . . ?
C4 N3 H3 116.9 . . ?
C2 N3 H3 116.9 . . ?
N5 C4 N3 117.2(11) . . ?
N5 C4 S1 124.2(10) . . ?
N3 C4 S1 118.3(9) . . ?
C4 N5 C6 120.8(11) . . ?
C4 N5 H5 119.6 . . ?
C6 N5 H5 119.6 . . ?
N5 C6 C6A 111.9(10) . . ?
N5 C6 C11 105.7(9) . . ?
C6A C6 C11 109.9(11) . . ?
N5 C6 H6 109.8 . . ?
C6A C6 H6 109.8 . . ?
C11 C6 H6 109.8 . . ?
C10A C6A C7 119.0(12) . . ?
C10A C6A C6 120.4(11) . . ?
C7 C6A C6 120.4(12) . . ?
C6A C7 C8 118.8(12) . . ?
C6A C7 H7 120.6 . . ?
C8 C7 H7 120.6 . . ?
C9 C8 C7 119.8(11) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C10 C9 C8 121.3(12) . . ?
C10 C9 H9 119.4 . . ?
C8 C9 H9 119.4 . . ?
C9 C10 C10A 119.5(13) . . ?
C9 C10 H10 120.3 . . ?
C10A C10 H10 120.2 . . ?
C6A C10A O1 122.0(11) . . ?
C6A C10A C10 121.4(12) . . ?
O1 C10A C10 116.5(11) . . ?
C13 C11 C6 112.2(11) . . ?
C13 C11 C2 121.9(9) . . ?
C6 C11 C2 105.2(10) . . ?
C13 C11 H11 105.4 . . ?
C6 C11 H11 105.5 . . ?
C2 C11 H11 105.4 . . ?
C2 C12 H12A 109.5 . . ?
C2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.4 . . ?
C2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.4 . . ?
H12B C12 H12C 109.5 . . ?
O2 C13 C14 122.8(11) . . ?
O2 C13 C11 117.0(11) . . ?
C14 C13 C11 120.2(10) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A

N3 H3 Cl1 0.86 2.37 3.137(10) 149 3_666
N5 H5 Cl1 0.86 2.59 3.299(10) 140 3_667

_refine_diff_density_max         0.57
_refine_diff_density_min         -0.49
_refine_diff_density_rms         0.23
