# Electronic Supplementary Material (ESI) for ChemComm.
# 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_Hardeep1b_01m
_database_code_depnum_ccdc_archive 'CCDC 2088565'
loop_
_audit_author_name
_audit_author_address
'Xavier Ottenwaelder' 'Concordia University'
_audit_update_record             
;
2021-06-07 deposited with the CCDC.	2021-08-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H15 N3 Ni O4 S'
_chemical_formula_sum            'C15 H15 N3 Ni O4 S'
_chemical_formula_weight         392.07

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'
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'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

_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+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   14.9422(17)
_cell_length_b                   14.9487(17)
_cell_length_c                   13.7186(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3064.3(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9944
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      26.99

_exptl_crystal_description       rhomb
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.700
_exptl_crystal_F_000             1616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.434
_exptl_crystal_size_mid          0.114
_exptl_crystal_size_min          0.106
_exptl_absorpt_coefficient_mu    1.429
_shelx_estimated_absorpt_T_min   0.576
_shelx_estimated_absorpt_T_max   0.863
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6474
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS-2016/2 - Bruker AXS'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            36308
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_av_R_equivalents  0.0710
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.362
_diffrn_reflns_theta_max         27.389
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3605
_reflns_number_gt                3227
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Refined as a 2-component twin. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0374P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3605
_refine_ls_number_parameters     310
_refine_ls_number_restraints     73
_refine_ls_R_factor_all          0.0323
_refine_ls_R_factor_gt           0.0278
_refine_ls_wR_factor_ref         0.0665
_refine_ls_wR_factor_gt          0.0651
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.045
_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
Ni1 Ni 0.46789(2) 0.33165(2) 0.62836(2) 0.01649(8) Uani 1 1 d . . . . .
O1 O 0.63466(12) 0.24723(13) 0.58728(16) 0.0383(5) Uani 1 1 d . . . . .
H1 H 0.640067 0.301723 0.583879 0.058 Uiso 1 1 calc DR U . . .
O2 O 0.57025(12) 0.39859(11) 0.61508(13) 0.0251(4) Uani 1 1 d D . . . .
N1 N 0.54376(14) 0.22533(14) 0.60772(14) 0.0200(4) Uani 1 1 d . . . . .
H1N H 0.542592 0.189733 0.667691 0.024 Uiso 1 1 calc R U . A 1
N2 N 0.39259(14) 0.42975(15) 0.63850(14) 0.0250(5) Uani 1 1 d . . . . .
N3 N 0.36250(15) 0.26469(15) 0.64747(17) 0.0303(5) Uani 1 1 d . . . . .
S1A S 0.3687(3) 0.1506(3) 0.6430(4) 0.0236(9) Uani 0.468(9) 1 d . . P B 1
O3A O 0.2804(6) 0.1160(6) 0.6176(8) 0.0415(19) Uani 0.468(9) 1 d . . P B 1
O4A O 0.4199(8) 0.1140(12) 0.7263(13) 0.025(2) Uani 0.468(9) 1 d . . P B 1
C1A C 0.5210(7) 0.1702(9) 0.5318(10) 0.0175(19) Uani 0.468(9) 1 d . . P B 1
C2A C 0.5762(6) 0.1545(5) 0.4518(6) 0.0224(16) Uani 0.468(9) 1 d . . P B 1
H2A H 0.631617 0.182538 0.447145 0.027 Uiso 0.468(9) 1 calc R U P B 1
C3A C 0.5478(8) 0.0971(5) 0.3798(6) 0.035(2) Uani 0.468(9) 1 d . . P B 1
H3A H 0.584697 0.086038 0.326513 0.043 Uiso 0.468(9) 1 calc R U P B 1
C4A C 0.4655(9) 0.0556(5) 0.3852(5) 0.0283(18) Uani 0.468(9) 1 d . . P B 1
H4A H 0.447891 0.016900 0.335681 0.034 Uiso 0.468(9) 1 calc R U P B 1
C5A C 0.4075(6) 0.0709(5) 0.4650(6) 0.0248(16) Uani 0.468(9) 1 d . . P B 1
H5A H 0.351677 0.043689 0.469149 0.030 Uiso 0.468(9) 1 calc R U P B 1
C6A C 0.4385(7) 0.1291(8) 0.5372(8) 0.0166(17) Uani 0.468(9) 1 d . . P B 1
S1B S 0.3486(3) 0.1671(3) 0.6459(3) 0.0201(7) Uani 0.532(9) 1 d . . P B 2
O3B O 0.2569(5) 0.1398(5) 0.6369(5) 0.0357(16) Uani 0.532(9) 1 d . . P B 2
O4B O 0.3933(7) 0.1238(10) 0.7268(11) 0.0203(17) Uani 0.532(9) 1 d . . P B 2
C1B C 0.4983(7) 0.1656(8) 0.5312(8) 0.0190(18) Uani 0.532(9) 1 d . . P B 2
C2B C 0.5437(5) 0.1384(6) 0.4477(5) 0.0256(16) Uani 0.532(9) 1 d . . P B 2
H2B H 0.601724 0.158850 0.437171 0.031 Uiso 0.532(9) 1 calc R U P B 2
C3B C 0.5054(7) 0.0825(6) 0.3806(4) 0.0289(17) Uani 0.532(9) 1 d . . P B 2
H3B H 0.537103 0.065327 0.325335 0.035 Uiso 0.532(9) 1 calc R U P B 2
C4B C 0.4184(6) 0.0513(4) 0.3956(5) 0.0279(14) Uani 0.532(9) 1 d . . P B 2
H4B H 0.392720 0.011795 0.351340 0.033 Uiso 0.532(9) 1 calc R U P B 2
C5B C 0.3691(6) 0.0796(5) 0.4781(5) 0.0274(14) Uani 0.532(9) 1 d . . P B 2
H5B H 0.310385 0.060905 0.487347 0.033 Uiso 0.532(9) 1 calc R U P B 2
C6B C 0.4104(6) 0.1362(7) 0.5453(7) 0.0180(16) Uani 0.532(9) 1 d . . P B 2
C7A C 0.2840(4) 0.3040(4) 0.6275(7) 0.029(2) Uani 0.468(9) 1 d . . P B 1
H7C H 0.236867 0.279007 0.667829 0.035 Uiso 0.468(9) 1 calc R U P B 1
H7D H 0.268210 0.295303 0.559589 0.035 Uiso 0.468(9) 1 calc R U P B 1
C7B C 0.2894(3) 0.3250(3) 0.6907(5) 0.0228(14) Uani 0.532(9) 1 d . . P B 2
H7A H 0.230772 0.300016 0.677190 0.027 Uiso 0.532(9) 1 calc R U P B 2
H7B H 0.296599 0.329204 0.760853 0.027 Uiso 0.532(9) 1 calc R U P B 2
C8 C 0.2966(2) 0.4066(2) 0.6502(2) 0.0442(8) Uani 1 1 d . . . . .
H8A H 0.267475 0.450562 0.691346 0.053 Uiso 0.468(9) 1 calc R U P B 2
H8B H 0.267319 0.406942 0.587098 0.053 Uiso 0.468(9) 1 calc R U P B 2
H8C H 0.260582 0.441999 0.605833 0.053 Uiso 0.532(9) 1 calc R U P B 1
H8D H 0.277400 0.419356 0.716280 0.053 Uiso 0.532(9) 1 calc R U P B 1
C9 C 0.4147(2) 0.51242(18) 0.63389(18) 0.0275(6) Uani 1 1 d . . . . .
H9 H 0.369028 0.554626 0.636021 0.033 Uiso 1 1 calc R U . . .
C10 C 0.5051(2) 0.54476(16) 0.62565(17) 0.0263(6) Uani 1 1 d . . . . .
C11 C 0.5194(3) 0.63768(18) 0.62841(18) 0.0441(9) Uani 1 1 d . . . . .
H11 H 0.470067 0.675610 0.630402 0.053 Uiso 1 1 calc R U . . .
C12 C 0.6019(3) 0.6735(2) 0.6283(2) 0.0500(10) Uani 1 1 d . . . . .
H12 H 0.609596 0.735255 0.629345 0.060 Uiso 1 1 calc R U . . .
C13 C 0.6749(3) 0.6171(3) 0.6265(2) 0.0518(11) Uani 1 1 d . . . . .
H13 H 0.732261 0.641200 0.629021 0.062 Uiso 1 1 calc R U . . .
C14 C 0.6643(2) 0.5245(2) 0.62105(19) 0.0394(7) Uani 1 1 d . . . . .
H14 H 0.714256 0.487530 0.618174 0.047 Uiso 1 1 calc R U . . .
C15 C 0.5782(2) 0.48715(17) 0.61990(17) 0.0253(6) Uani 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
Ni1 O2 1.8369(17) . ?
Ni1 N2 1.854(2) . ?
Ni1 N3 1.884(2) . ?
Ni1 N1 1.973(2) . ?
O1 N1 1.425(3) . ?
O1 H1 0.8200 . ?
O2 C15 1.331(3) . ?
N1 C1A 1.371(12) . ?
N1 C1B 1.537(11) . ?
N1 H1N 0.9800 . ?
N2 C9 1.281(3) . ?
N2 C8 1.484(4) . ?
N3 C7A 1.341(6) . ?
N3 S1B 1.473(5) . ?
N3 C7B 1.536(5) . ?
N3 S1A 1.710(6) . ?
S1A O3A 1.460(11) . ?
S1A O4A 1.480(16) . ?
S1A C6A 1.815(10) . ?
C1A C6A 1.380(10) . ?
C1A C2A 1.392(11) . ?
C2A C3A 1.377(9) . ?
C2A H2A 0.9300 . ?
C3A C4A 1.379(11) . ?
C3A H3A 0.9300 . ?
C4A C5A 1.415(10) . ?
C4A H4A 0.9300 . ?
C5A C6A 1.398(11) . ?
C5A H5A 0.9300 . ?
S1B O3B 1.435(9) . ?
S1B O4B 1.448(13) . ?
S1B C6B 1.724(8) . ?
C1B C2B 1.392(9) . ?
C1B C6B 1.399(8) . ?
C2B C3B 1.369(10) . ?
C2B H2B 0.9300 . ?
C3B C4B 1.397(10) . ?
C3B H3B 0.9300 . ?
C4B C5B 1.414(8) . ?
C4B H4B 0.9300 . ?
C5B C6B 1.394(9) . ?
C5B H5B 0.9300 . ?
C7A C8 1.575(8) . ?
C7A H7C 0.9700 . ?
C7A H7D 0.9700 . ?
C7B C8 1.345(5) . ?
C7B H7A 0.9700 . ?
C7B H7B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 H8C 0.9700 . ?
C8 H8D 0.9700 . ?
C9 C10 1.440(4) . ?
C9 H9 0.9300 . ?
C10 C15 1.393(4) . ?
C10 C11 1.406(4) . ?
C11 C12 1.345(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.379(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.396(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.402(4) . ?
C14 H14 0.9300 . ?

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
O2 Ni1 N2 94.70(9) . . ?
O2 Ni1 N3 177.57(9) . . ?
N2 Ni1 N3 84.40(11) . . ?
O2 Ni1 N1 86.91(8) . . ?
N2 Ni1 N1 175.58(9) . . ?
N3 Ni1 N1 94.15(10) . . ?
N1 O1 H1 109.5 . . ?
C15 O2 Ni1 127.70(19) . . ?
C1A N1 O1 103.0(5) . . ?
O1 N1 C1B 114.9(4) . . ?
C1A N1 Ni1 116.8(6) . . ?
O1 N1 Ni1 113.01(14) . . ?
C1B N1 Ni1 108.2(5) . . ?
C1A N1 H1N 107.9 . . ?
O1 N1 H1N 107.9 . . ?
Ni1 N1 H1N 107.9 . . ?
C9 N2 C8 118.7(2) . . ?
C9 N2 Ni1 127.1(2) . . ?
C8 N2 Ni1 114.20(19) . . ?
S1B N3 C7B 119.1(3) . . ?
C7A N3 S1A 118.5(4) . . ?
C7A N3 Ni1 118.0(3) . . ?
S1B N3 Ni1 129.9(3) . . ?
C7B N3 Ni1 109.7(2) . . ?
S1A N3 Ni1 118.7(2) . . ?
O3A S1A O4A 121.4(9) . . ?
O3A S1A N3 108.2(4) . . ?
O4A S1A N3 111.7(8) . . ?
O3A S1A C6A 105.4(6) . . ?
O4A S1A C6A 104.8(6) . . ?
N3 S1A C6A 103.6(5) . . ?
N1 C1A C6A 116.6(9) . . ?
N1 C1A C2A 123.6(8) . . ?
C6A C1A C2A 119.8(8) . . ?
C3A C2A C1A 119.2(8) . . ?
C3A C2A H2A 120.4 . . ?
C1A C2A H2A 120.4 . . ?
C2A C3A C4A 121.1(7) . . ?
C2A C3A H3A 119.4 . . ?
C4A C3A H3A 119.4 . . ?
C3A C4A C5A 121.0(7) . . ?
C3A C4A H4A 119.5 . . ?
C5A C4A H4A 119.5 . . ?
C6A C5A C4A 116.5(7) . . ?
C6A C5A H5A 121.7 . . ?
C4A C5A H5A 121.7 . . ?
C1A C6A C5A 122.3(7) . . ?
C1A C6A S1A 118.6(8) . . ?
C5A C6A S1A 119.1(7) . . ?
O3B S1B O4B 112.3(7) . . ?
O3B S1B N3 114.7(4) . . ?
O4B S1B N3 111.6(7) . . ?
O3B S1B C6B 111.4(5) . . ?
O4B S1B C6B 104.3(6) . . ?
N3 S1B C6B 101.6(4) . . ?
C2B C1B C6B 118.7(7) . . ?
C2B C1B N1 121.1(7) . . ?
C6B C1B N1 120.2(7) . . ?
C3B C2B C1B 121.8(7) . . ?
C3B C2B H2B 119.1 . . ?
C1B C2B H2B 119.1 . . ?
C2B C3B C4B 119.6(6) . . ?
C2B C3B H3B 120.2 . . ?
C4B C3B H3B 120.2 . . ?
C3B C4B C5B 120.2(6) . . ?
C3B C4B H4B 119.9 . . ?
C5B C4B H4B 119.9 . . ?
C6B C5B C4B 118.7(6) . . ?
C6B C5B H5B 120.6 . . ?
C4B C5B H5B 120.6 . . ?
C5B C6B C1B 121.0(6) . . ?
C5B C6B S1B 117.1(6) . . ?
C1B C6B S1B 122.0(7) . . ?
N3 C7A C8 106.3(5) . . ?
N3 C7A H7C 110.5 . . ?
C8 C7A H7C 110.5 . . ?
N3 C7A H7D 110.5 . . ?
C8 C7A H7D 110.5 . . ?
H7C C7A H7D 108.7 . . ?
C8 C7B N3 108.4(3) . . ?
C8 C7B H7A 110.0 . . ?
N3 C7B H7A 110.0 . . ?
C8 C7B H7B 110.0 . . ?
N3 C7B H7B 110.0 . . ?
H7A C7B H7B 108.4 . . ?
C7B C8 N2 109.5(3) . . ?
N2 C8 C7A 108.8(3) . . ?
C7B C8 H8A 109.8 . . ?
N2 C8 H8A 109.8 . . ?
C7B C8 H8B 109.8 . . ?
N2 C8 H8B 109.8 . . ?
H8A C8 H8B 108.2 . . ?
N2 C8 H8C 109.9 . . ?
C7A C8 H8C 109.9 . . ?
N2 C8 H8D 109.9 . . ?
C7A C8 H8D 109.9 . . ?
H8C C8 H8D 108.3 . . ?
N2 C9 C10 124.8(3) . . ?
N2 C9 H9 117.6 . . ?
C10 C9 H9 117.6 . . ?
C15 C10 C11 119.6(3) . . ?
C15 C10 C9 122.2(2) . . ?
C11 C10 C9 118.1(3) . . ?
C12 C11 C10 122.2(4) . . ?
C12 C11 H11 118.9 . . ?
C10 C11 H11 118.9 . . ?
C11 C12 C13 118.8(3) . . ?
C11 C12 H12 120.6 . . ?
C13 C12 H12 120.6 . . ?
C12 C13 C14 121.1(3) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 H13 119.4 . . ?
C13 C14 C15 120.0(3) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
O2 C15 C10 123.2(3) . . ?
O2 C15 C14 118.6(3) . . ?
C10 C15 C14 118.2(3) . . ?

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
_geom_hbond_publ_flag
O1 H1 O2 0.82 1.84 2.488(2) 135.6 . yes
N1 H1N^a S1A^a 0.98 2.97 3.828(6) 146.3 3_656 yes
N1 H1N^a O4A^a 0.98 2.30 2.974(17) 125.1 . yes
N1 H1N^a O4A^a 0.98 1.93 2.872(19) 161.4 3_656 yes
N1 H1N^a O4A^a 0.98 2.30 2.974(17) 125.1 . yes
N1 H1N^a O4A^a 0.98 1.93 2.872(19) 161.4 3_656 yes

_refine_diff_density_max         0.332
_refine_diff_density_min         -0.464
_refine_diff_density_rms         0.062



####################################################################### 
# 
# 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_Hardeep4_0m
_database_code_depnum_ccdc_archive 'CCDC 2088571'
loop_
_audit_author_name
_audit_author_address
'Xavier Ottenwaelder' 'Concordia University'
_audit_update_record             
;
2021-06-07 deposited with the CCDC.	2021-08-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H15 N3 Ni O3 S, 0.5 (H2 O)'
_chemical_formula_sum            'C15 H16 N3 Ni O3.50 S'
_chemical_formula_weight         385.08

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'
Ni Ni -3.0029 0.5091 '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      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                   11.9552(9)
_cell_length_b                   12.1760(9)
_cell_length_c                   12.7970(9)
_cell_angle_alpha                98.838(4)
_cell_angle_beta                 112.789(4)
_cell_angle_gamma                108.273(4)
_cell_volume                     1548.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    8338
_cell_measurement_theta_min      3.95
_cell_measurement_theta_max      68.25

_exptl_crystal_description       plate
_exptl_crystal_colour            bronze
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.652
_exptl_crystal_F_000             796
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.189
_exptl_crystal_size_mid          0.109
_exptl_crystal_size_min          0.037
_exptl_absorpt_coefficient_mu    3.274
_shelx_estimated_absorpt_T_min   0.577
_shelx_estimated_absorpt_T_max   0.888
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6606
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_process_details   
; 
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., 
 J. Appl. Cryst. 48 (2015) 3-10 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20646
_diffrn_reflns_av_unetI/netI     0.0453
_diffrn_reflns_av_R_equivalents  0.0554
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.947
_diffrn_reflns_theta_max         68.802
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.930
_diffrn_measured_fraction_theta_full 0.940
_diffrn_reflns_Laue_measured_fraction_max 0.930
_diffrn_reflns_Laue_measured_fraction_full 0.940
_diffrn_reflns_point_group_measured_fraction_max 0.930
_diffrn_reflns_point_group_measured_fraction_full 0.940
_reflns_number_total             5327
_reflns_number_gt                4556
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+3.7283P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5327
_refine_ls_number_parameters     432
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0375
_refine_ls_wR_factor_ref         0.0953
_refine_ls_wR_factor_gt          0.0914
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_restrained_S_all      1.097
_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
Ni1 Ni 0.74740(5) 0.30731(5) 0.34498(4) 0.01543(14) Uani 1 1 d . . . . .
Ni2 Ni 0.51892(5) 0.65310(4) 0.89045(4) 0.01486(14) Uani 1 1 d . . . . .
S1 S 0.59635(9) 0.03004(7) 0.22768(7) 0.01864(18) Uani 1 1 d . . . . .
S2 S 0.69943(8) 0.72436(7) 0.77621(7) 0.01684(17) Uani 1 1 d . . . . .
O1 O 0.7895(2) 0.45895(19) 0.44206(19) 0.0179(5) Uani 1 1 d . . . . .
O2 O 0.6136(3) -0.0725(2) 0.1732(2) 0.0260(6) Uani 1 1 d . . . . .
O3 O 0.4619(2) 0.0233(2) 0.1707(2) 0.0242(5) Uani 1 1 d . . . . .
O4 O 0.4484(2) 0.68694(19) 0.98799(19) 0.0206(5) Uani 1 1 d . . . . .
O5 O 0.7635(2) 0.6757(2) 0.7174(2) 0.0241(5) Uani 1 1 d . . . . .
O6 O 0.6480(2) 0.8076(2) 0.7249(2) 0.0222(5) Uani 1 1 d . . . . .
O7 O 0.7710(3) 0.4424(2) 0.6476(2) 0.0259(6) Uani 1 1 d . . . . .
H7WA H 0.767(4) 0.504(4) 0.684(4) 0.038(12) Uiso 1 1 d . . . . .
H7WB H 0.796(5) 0.464(4) 0.594(4) 0.046(13) Uiso 1 1 d . . . . .
N1 N 0.6316(3) 0.2369(2) 0.4137(2) 0.0173(6) Uani 1 1 d . . . . .
H1A H 0.648305 0.296691 0.476971 0.021 Uiso 1 1 calc R U . . .
H1AB H 0.545761 0.213142 0.358134 0.021 Uiso 1 1 calc R U . . .
N2 N 0.7087(3) 0.1541(2) 0.2471(2) 0.0200(6) Uani 1 1 d . . . . .
N3 N 0.8551(3) 0.3682(2) 0.2767(2) 0.0177(6) Uani 1 1 d . . . . .
N4 N 0.6379(3) 0.8253(2) 0.9631(2) 0.0149(5) Uani 1 1 d . . . . .
H4A H 0.613804 0.864309 0.908532 0.018 Uiso 1 1 calc R U . . .
H4AB H 0.626296 0.856423 1.025551 0.018 Uiso 1 1 calc R U . . .
N5 N 0.5963(3) 0.6199(2) 0.7930(2) 0.0185(6) Uani 1 1 d . . . . .
N6 N 0.4097(3) 0.4887(2) 0.8258(2) 0.0166(6) Uani 1 1 d . . . . .
C1 C 0.6436(3) 0.1342(3) 0.4535(3) 0.0167(7) Uani 1 1 d . . . . .
C2 C 0.6672(3) 0.1343(3) 0.5688(3) 0.0187(7) Uani 1 1 d . . . . .
H2 H 0.676318 0.202821 0.623564 0.022 Uiso 1 1 calc R U . . .
C3 C 0.6774(3) 0.0335(3) 0.6037(3) 0.0226(7) Uani 1 1 d . . . . .
H3 H 0.691428 0.033159 0.681956 0.027 Uiso 1 1 calc R U . . .
C4 C 0.6673(3) -0.0661(3) 0.5262(3) 0.0226(7) Uani 1 1 d . . . . .
H4 H 0.675938 -0.133752 0.551399 0.027 Uiso 1 1 calc R U . . .
C5 C 0.6444(3) -0.0660(3) 0.4112(3) 0.0204(7) Uani 1 1 d . . . . .
H5 H 0.637304 -0.133810 0.357076 0.024 Uiso 1 1 calc R U . . .
C6 C 0.6320(3) 0.0336(3) 0.3754(3) 0.0164(7) Uani 1 1 d . . . . .
C7 C 0.7332(4) 0.1634(3) 0.1432(3) 0.0212(7) Uani 1 1 d . . . . .
H7A H 0.660820 0.174828 0.080849 0.025 Uiso 1 1 calc R U . . .
H7AB H 0.741372 0.089707 0.108145 0.025 Uiso 1 1 calc R U . . .
C8 C 0.8625(3) 0.2739(3) 0.1958(3) 0.0209(7) Uani 1 1 d . . . . .
H8A H 0.937876 0.253759 0.240361 0.025 Uiso 1 1 calc R U . . .
H8AB H 0.875867 0.303176 0.131707 0.025 Uiso 1 1 calc R U . . .
C9 C 0.9236(3) 0.4810(3) 0.2948(3) 0.0190(7) Uani 1 1 d . . . . .
H9 H 0.974077 0.498095 0.252797 0.023 Uiso 1 1 calc R U . . .
C10 C 0.9295(3) 0.5827(3) 0.3732(3) 0.0197(7) Uani 1 1 d . . . . .
C11 C 1.0035(4) 0.7007(3) 0.3786(3) 0.0259(8) Uani 1 1 d . . . . .
H11 H 1.050048 0.710265 0.332674 0.031 Uiso 1 1 calc R U . . .
C12 C 1.0103(4) 0.8023(3) 0.4485(3) 0.0289(8) Uani 1 1 d . . . . .
H12 H 1.060600 0.881556 0.451300 0.035 Uiso 1 1 calc R U . . .
C13 C 0.9410(4) 0.7864(3) 0.5157(3) 0.0272(8) Uani 1 1 d . . . . .
H13 H 0.944513 0.855992 0.564384 0.033 Uiso 1 1 calc R U . . .
C14 C 0.8680(3) 0.6721(3) 0.5127(3) 0.0213(7) Uani 1 1 d . . . . .
H14 H 0.822237 0.664187 0.559344 0.026 Uiso 1 1 calc R U . . .
C15 C 0.8603(3) 0.5668(3) 0.4415(3) 0.0178(7) Uani 1 1 d . . . . .
C16 C 0.7765(3) 0.8519(3) 1.0052(3) 0.0152(6) Uani 1 1 d . . . . .
C17 C 0.8688(3) 0.9135(3) 1.1242(3) 0.0187(7) Uani 1 1 d . . . . .
H17 H 0.841067 0.940376 1.179756 0.022 Uiso 1 1 calc R U . . .
C18 C 1.0018(3) 0.9357(3) 1.1620(3) 0.0226(7) Uani 1 1 d . . . . .
H18 H 1.064794 0.977900 1.243440 0.027 Uiso 1 1 calc R U . . .
C19 C 1.0432(3) 0.8966(3) 1.0815(3) 0.0226(7) Uani 1 1 d . . . . .
H19 H 1.134549 0.913575 1.107520 0.027 Uiso 1 1 calc R U . . .
C20 C 0.9513(3) 0.8328(3) 0.9633(3) 0.0192(7) Uani 1 1 d . . . . .
H20 H 0.979257 0.804971 0.908275 0.023 Uiso 1 1 calc R U . . .
C21 C 0.8185(3) 0.8097(3) 0.9256(3) 0.0158(6) Uani 1 1 d . . . . .
C22 C 0.5047(3) 0.5070(3) 0.6910(3) 0.0213(7) Uani 1 1 d . . . . .
H22A H 0.554243 0.474502 0.657689 0.026 Uiso 1 1 calc R U . . .
H22B H 0.437506 0.522270 0.627081 0.026 Uiso 1 1 calc R U . . .
C23 C 0.4398(3) 0.4198(3) 0.7430(3) 0.0197(7) Uani 1 1 d . . . . .
H23A H 0.356948 0.352838 0.678562 0.024 Uiso 1 1 calc R U . . .
H23B H 0.500439 0.384085 0.786020 0.024 Uiso 1 1 calc R U . . .
C24 C 0.3184(3) 0.4311(3) 0.8518(3) 0.0192(7) Uani 1 1 d . . . . .
H24 H 0.271822 0.345557 0.813995 0.023 Uiso 1 1 calc R U . . .
C25 C 0.2818(3) 0.4864(3) 0.9335(3) 0.0194(7) Uani 1 1 d . . . . .
C26 C 0.1764(3) 0.4144(3) 0.9500(3) 0.0234(7) Uani 1 1 d . . . . .
H26 H 0.131681 0.329551 0.907898 0.028 Uiso 1 1 calc R U . . .
C27 C 0.1364(4) 0.4637(3) 1.0258(3) 0.0275(8) Uani 1 1 d . . . . .
H27 H 0.065341 0.413489 1.036366 0.033 Uiso 1 1 calc R U . . .
C28 C 0.2016(4) 0.5886(3) 1.0870(3) 0.0250(8) Uani 1 1 d . . . . .
H28 H 0.174625 0.623029 1.139678 0.030 Uiso 1 1 calc R U . . .
C29 C 0.3043(3) 0.6624(3) 1.0722(3) 0.0219(7) Uani 1 1 d . . . . .
H29 H 0.346353 0.747343 1.113781 0.026 Uiso 1 1 calc R U . . .
C30 C 0.3478(3) 0.6129(3) 0.9953(3) 0.0185(7) Uani 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
Ni1 O1 1.853(2) . ?
Ni1 N3 1.856(3) . ?
Ni1 N2 1.885(3) . ?
Ni1 N1 1.963(3) . ?
Ni2 O4 1.820(2) . ?
Ni2 N6 1.847(3) . ?
Ni2 N5 1.883(3) . ?
Ni2 N4 1.946(3) . ?
S1 O2 1.447(2) . ?
S1 O3 1.453(2) . ?
S1 N2 1.582(3) . ?
S1 C6 1.760(3) . ?
S2 O5 1.449(2) . ?
S2 O6 1.455(2) . ?
S2 N5 1.578(3) . ?
S2 C21 1.765(3) . ?
O1 C15 1.323(4) . ?
O4 C30 1.305(4) . ?
O7 H7WA 0.85(4) . ?
O7 H7WB 0.90(5) . ?
N1 C1 1.447(4) . ?
N1 H1A 0.9100 . ?
N1 H1AB 0.9100 . ?
N2 C7 1.482(4) . ?
N3 C9 1.288(4) . ?
N3 C8 1.473(4) . ?
N4 C16 1.434(4) . ?
N4 H4A 0.9100 . ?
N4 H4AB 0.9100 . ?
N5 C22 1.480(4) . ?
N6 C24 1.292(4) . ?
N6 C23 1.472(4) . ?
C1 C6 1.389(4) . ?
C1 C2 1.390(4) . ?
C2 C3 1.393(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.384(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.390(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.390(4) . ?
C5 H5 0.9500 . ?
C7 C8 1.505(5) . ?
C7 H7A 0.9900 . ?
C7 H7AB 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8AB 0.9900 . ?
C9 C10 1.433(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.406(5) . ?
C10 C15 1.414(5) . ?
C11 C12 1.371(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.402(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.377(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.409(4) . ?
C14 H14 0.9500 . ?
C16 C17 1.388(4) . ?
C16 C21 1.398(4) . ?
C17 C18 1.389(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.387(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.383(5) . ?
C19 H19 0.9500 . ?
C20 C21 1.385(5) . ?
C20 H20 0.9500 . ?
C22 C23 1.508(5) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.435(5) . ?
C24 H24 0.9500 . ?
C25 C26 1.405(5) . ?
C25 C30 1.415(5) . ?
C26 C27 1.374(5) . ?
C26 H26 0.9500 . ?
C27 C28 1.397(5) . ?
C27 H27 0.9500 . ?
C28 C29 1.375(5) . ?
C28 H28 0.9500 . ?
C29 C30 1.419(5) . ?
C29 H29 0.9500 . ?

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 Ni1 N3 94.55(11) . . ?
O1 Ni1 N2 178.67(12) . . ?
N3 Ni1 N2 84.49(12) . . ?
O1 Ni1 N1 87.51(10) . . ?
N3 Ni1 N1 177.94(11) . . ?
N2 Ni1 N1 93.45(11) . . ?
O4 Ni2 N6 95.46(11) . . ?
O4 Ni2 N5 178.51(12) . . ?
N6 Ni2 N5 85.41(12) . . ?
O4 Ni2 N4 84.33(10) . . ?
N6 Ni2 N4 178.09(12) . . ?
N5 Ni2 N4 94.77(11) . . ?
O2 S1 O3 114.42(14) . . ?
O2 S1 N2 110.50(15) . . ?
O3 S1 N2 114.75(14) . . ?
O2 S1 C6 108.05(14) . . ?
O3 S1 C6 106.07(14) . . ?
N2 S1 C6 101.97(14) . . ?
O5 S2 O6 114.11(14) . . ?
O5 S2 N5 111.21(14) . . ?
O6 S2 N5 114.41(15) . . ?
O5 S2 C21 108.42(15) . . ?
O6 S2 C21 105.94(14) . . ?
N5 S2 C21 101.66(14) . . ?
C15 O1 Ni1 127.5(2) . . ?
C30 O4 Ni2 127.8(2) . . ?
H7WA O7 H7WB 106(4) . . ?
C1 N1 Ni1 116.7(2) . . ?
C1 N1 H1A 108.1 . . ?
Ni1 N1 H1A 108.1 . . ?
C1 N1 H1AB 108.1 . . ?
Ni1 N1 H1AB 108.1 . . ?
H1A N1 H1AB 107.3 . . ?
C7 N2 S1 115.7(2) . . ?
C7 N2 Ni1 112.1(2) . . ?
S1 N2 Ni1 124.47(16) . . ?
C9 N3 C8 118.6(3) . . ?
C9 N3 Ni1 127.2(2) . . ?
C8 N3 Ni1 114.2(2) . . ?
C16 N4 Ni2 115.26(18) . . ?
C16 N4 H4A 108.5 . . ?
Ni2 N4 H4A 108.5 . . ?
C16 N4 H4AB 108.5 . . ?
Ni2 N4 H4AB 108.5 . . ?
H4A N4 H4AB 107.5 . . ?
C22 N5 S2 118.3(2) . . ?
C22 N5 Ni2 111.6(2) . . ?
S2 N5 Ni2 122.24(15) . . ?
C24 N6 C23 119.3(3) . . ?
C24 N6 Ni2 126.3(2) . . ?
C23 N6 Ni2 114.2(2) . . ?
C6 C1 C2 119.1(3) . . ?
C6 C1 N1 119.5(3) . . ?
C2 C1 N1 121.4(3) . . ?
C1 C2 C3 119.7(3) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C4 C3 C2 121.1(3) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 119.3(3) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C4 C5 C6 119.8(3) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C1 C6 C5 121.0(3) . . ?
C1 C6 S1 119.6(2) . . ?
C5 C6 S1 119.4(2) . . ?
N2 C7 C8 103.3(3) . . ?
N2 C7 H7A 111.1 . . ?
C8 C7 H7A 111.1 . . ?
N2 C7 H7AB 111.1 . . ?
C8 C7 H7AB 111.1 . . ?
H7A C7 H7AB 109.1 . . ?
N3 C8 C7 107.2(3) . . ?
N3 C8 H8A 110.3 . . ?
C7 C8 H8A 110.3 . . ?
N3 C8 H8AB 110.3 . . ?
C7 C8 H8AB 110.3 . . ?
H8A C8 H8AB 108.5 . . ?
N3 C9 C10 125.1(3) . . ?
N3 C9 H9 117.5 . . ?
C10 C9 H9 117.5 . . ?
C11 C10 C15 119.9(3) . . ?
C11 C10 C9 118.3(3) . . ?
C15 C10 C9 121.8(3) . . ?
C12 C11 C10 121.7(3) . . ?
C12 C11 H11 119.1 . . ?
C10 C11 H11 119.1 . . ?
C11 C12 C13 118.3(3) . . ?
C11 C12 H12 120.8 . . ?
C13 C12 H12 120.8 . . ?
C14 C13 C12 121.4(3) . . ?
C14 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C13 C14 C15 121.0(3) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 H14 119.5 . . ?
O1 C15 C14 118.8(3) . . ?
O1 C15 C10 123.5(3) . . ?
C14 C15 C10 117.7(3) . . ?
C17 C16 C21 119.1(3) . . ?
C17 C16 N4 121.7(3) . . ?
C21 C16 N4 119.1(3) . . ?
C16 C17 C18 120.0(3) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C19 C18 C17 120.4(3) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C20 C19 C18 120.0(3) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C19 C20 C21 119.7(3) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
C20 C21 C16 120.7(3) . . ?
C20 C21 S2 120.3(2) . . ?
C16 C21 S2 119.1(2) . . ?
N5 C22 C23 104.5(3) . . ?
N5 C22 H22A 110.8 . . ?
C23 C22 H22A 110.8 . . ?
N5 C22 H22B 110.8 . . ?
C23 C22 H22B 110.8 . . ?
H22A C22 H22B 108.9 . . ?
N6 C23 C22 107.7(2) . . ?
N6 C23 H23A 110.2 . . ?
C22 C23 H23A 110.2 . . ?
N6 C23 H23B 110.2 . . ?
C22 C23 H23B 110.2 . . ?
H23A C23 H23B 108.5 . . ?
N6 C24 C25 125.1(3) . . ?
N6 C24 H24 117.5 . . ?
C25 C24 H24 117.5 . . ?
C26 C25 C30 119.4(3) . . ?
C26 C25 C24 119.5(3) . . ?
C30 C25 C24 121.1(3) . . ?
C27 C26 C25 121.6(3) . . ?
C27 C26 H26 119.2 . . ?
C25 C26 H26 119.2 . . ?
C26 C27 C28 119.1(3) . . ?
C26 C27 H27 120.4 . . ?
C28 C27 H27 120.4 . . ?
C29 C28 C27 121.1(3) . . ?
C29 C28 H28 119.4 . . ?
C27 C28 H28 119.4 . . ?
C28 C29 C30 120.5(3) . . ?
C28 C29 H29 119.7 . . ?
C30 C29 H29 119.7 . . ?
O4 C30 C25 124.0(3) . . ?
O4 C30 C29 117.7(3) . . ?
C25 C30 C29 118.3(3) . . ?

_refine_diff_density_max         0.353
_refine_diff_density_min         -0.425
_refine_diff_density_rms         0.081



####################################################################### 
# 
# 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_Fei14s_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 2088573'
loop_
_audit_author_name
_audit_author_address
'Xavier Ottenwaelder' 'Concordia University'
_audit_update_record             
;
2021-06-07 deposited with the CCDC.	2021-08-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H28 Cu N6 O7 S2, C H2 Cl2'
_chemical_formula_sum            'C31 H30 Cl2 Cu N6 O7 S2'
_chemical_formula_weight         797.17

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'
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'
Cl Cl 0.1484 0.1585 '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                   10.967(2)
_cell_length_b                   14.103(3)
_cell_length_c                   21.624(4)
_cell_angle_alpha                90
_cell_angle_beta                 104.421(2)
_cell_angle_gamma                90
_cell_volume                     3239.2(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    112(2)
_cell_measurement_reflns_used    9920
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      27.47

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.635
_exptl_crystal_F_000             1636
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.563
_exptl_crystal_size_mid          0.430
_exptl_crystal_size_min          0.226
_exptl_absorpt_coefficient_mu    1.027
_shelx_estimated_absorpt_T_min   0.595
_shelx_estimated_absorpt_T_max   0.801
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6366
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS-2016/2 - Bruker AXS'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      112(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            32350
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_av_R_equivalents  0.0478
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.741
_diffrn_reflns_theta_max         25.525
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6030
_reflns_number_gt                4835
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0363P)²+3.9130P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6030
_refine_ls_number_parameters     495
_refine_ls_number_restraints     38
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0386
_refine_ls_wR_factor_ref         0.0942
_refine_ls_wR_factor_gt          0.0878
_refine_ls_goodness_of_fit_ref   1.051
_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 0.43379(3) 0.79021(2) 0.77002(2) 0.02047(10) Uani 1 1 d . . . . .
S1 S 0.80490(6) 0.65661(5) 0.83753(4) 0.02444(17) Uani 1 1 d . . . . .
S2 S 0.23522(7) 0.51295(5) 0.70384(4) 0.02442(17) Uani 1 1 d . . . . .
O3 O 0.58459(19) 0.44844(14) 0.77782(11) 0.0332(5) Uani 1 1 d . . . . .
O4 O 0.38636(17) 0.75808(13) 0.68238(9) 0.0238(4) Uani 1 1 d . . . . .
O5 O 0.50250(17) 0.77229(13) 0.85868(9) 0.0231(4) Uani 1 1 d . . . . .
O6 O 0.93676(18) 0.66859(15) 0.84631(10) 0.0322(5) Uani 1 1 d . . . . .
O7 O 0.75789(19) 0.58082(14) 0.86824(10) 0.0300(5) Uani 1 1 d . . . . .
O8 O 0.33179(18) 0.47509(14) 0.67803(10) 0.0285(5) Uani 1 1 d . . . . .
O9 O 0.11478(18) 0.46891(14) 0.69042(10) 0.0284(5) Uani 1 1 d . . . . .
N1A N 0.5317(11) 0.6000(6) 0.7648(4) 0.025(2) Uani 0.58(3) 1 d . U P A 1
N2A N 0.5188(11) 0.5188(6) 0.7829(4) 0.027(2) Uani 0.58(3) 1 d . U P A 1
N1B N 0.4822(14) 0.5871(6) 0.7824(5) 0.017(3) Uani 0.42(3) 1 d . U P A 2
N2B N 0.5675(15) 0.5373(8) 0.7680(5) 0.022(3) Uani 0.42(3) 1 d . U P A 2
N3 N 0.5818(2) 0.86138(15) 0.75886(11) 0.0190(5) Uani 1 1 d . . . . .
N4 N 0.2601(2) 0.76701(16) 0.77648(12) 0.0234(5) Uani 1 1 d . . . . .
N5 N 0.7501(2) 0.75140(18) 0.85921(12) 0.0239(6) Uani 1 1 d . . . . .
H5N H 0.690(3) 0.744(2) 0.8630(16) 0.029 Uiso 1 1 d . U . . .
N6 N 0.2134(2) 0.61967(17) 0.68046(12) 0.0242(6) Uani 1 1 d . . . . .
H6N H 0.272(3) 0.649(2) 0.6779(15) 0.029 Uiso 1 1 d . U . . .
C1 C 0.6285(3) 0.6013(2) 0.72802(16) 0.0356(8) Uani 1 1 d . . . . .
C2 C 0.5845(3) 0.5914(2) 0.66341(15) 0.0340(7) Uani 1 1 d . . . . .
H2 H 0.506260 0.560797 0.646166 0.041 Uiso 1 1 calc R U . . .
C3 C 0.6536(3) 0.6258(2) 0.62372(15) 0.0313(7) Uani 1 1 d . . . . .
H3 H 0.623959 0.619170 0.578752 0.038 Uiso 1 1 calc R U . . .
C4 C 0.7656(3) 0.6697(2) 0.64951(16) 0.0351(8) Uani 1 1 d . . . . .
H4 H 0.813077 0.694917 0.622079 0.042 Uiso 1 1 calc R U . . .
C5 C 0.8105(3) 0.6780(2) 0.71394(15) 0.0305(7) Uani 1 1 d . . . . .
H5 H 0.889304 0.708034 0.730869 0.037 Uiso 1 1 calc R U . . .
C6 C 0.7432(3) 0.6434(2) 0.75459(14) 0.0253(6) Uani 1 1 d . . . . .
C7 C 0.7842(3) 0.8440(2) 0.83922(14) 0.0248(6) Uani 1 1 d . . . . .
H7A H 0.829470 0.836045 0.805262 0.030 Uiso 1 1 calc R U . . .
H7AB H 0.841462 0.876154 0.875851 0.030 Uiso 1 1 calc R U . . .
C8 C 0.6689(3) 0.9044(2) 0.81457(13) 0.0238(6) Uani 1 1 d . . . . .
H8A H 0.624931 0.913383 0.848947 0.029 Uiso 1 1 calc R U . . .
H8AB H 0.695064 0.967592 0.802625 0.029 Uiso 1 1 calc R U . . .
C9 C 0.6027(2) 0.88162(19) 0.70483(13) 0.0206(6) Uani 1 1 d . . . . .
H9 H 0.672943 0.921518 0.705698 0.025 Uiso 1 1 calc R U . . .
C10 C 0.5328(2) 0.85109(19) 0.64350(13) 0.0216(6) Uani 1 1 d . . . . .
C11 C 0.5691(3) 0.8849(2) 0.58965(14) 0.0285(7) Uani 1 1 d . . . . .
H11 H 0.638237 0.927353 0.595265 0.034 Uiso 1 1 calc R U . . .
C12 C 0.5076(3) 0.8581(2) 0.52987(15) 0.0323(7) Uani 1 1 d . . . . .
H12 H 0.532561 0.882006 0.493833 0.039 Uiso 1 1 calc R U . . .
C13 C 0.4076(3) 0.7952(2) 0.52198(15) 0.0332(7) Uani 1 1 d . . . . .
H13 H 0.365366 0.774800 0.480272 0.040 Uiso 1 1 calc R U . . .
C14 C 0.3691(3) 0.7623(2) 0.57324(14) 0.0280(7) Uani 1 1 d . . . . .
H14 H 0.299953 0.719741 0.566604 0.034 Uiso 1 1 calc R U . . .
C15 C 0.4289(3) 0.78977(19) 0.63503(13) 0.0224(6) Uani 1 1 d . . . . .
C16 C 0.4161(3) 0.5221(3) 0.81832(16) 0.0451(9) Uani 1 1 d . . . . .
C17 C 0.4574(3) 0.5134(3) 0.88305(17) 0.0472(10) Uani 1 1 d . . . . .
H17 H 0.544456 0.519669 0.903342 0.057 Uiso 1 1 calc R U . . .
C18 C 0.3725(3) 0.4957(2) 0.91847(15) 0.0323(7) Uani 1 1 d . . . . .
H18 H 0.400701 0.489374 0.963514 0.039 Uiso 1 1 calc R U . . .
C19 C 0.2476(3) 0.4871(2) 0.88946(16) 0.0326(7) Uani 1 1 d . . . . .
H19 H 0.188893 0.476125 0.914400 0.039 Uiso 1 1 calc R U . . .
C20 C 0.2067(3) 0.4941(2) 0.82455(15) 0.0283(7) Uani 1 1 d . . . . .
H20 H 0.119664 0.487057 0.804500 0.034 Uiso 1 1 calc R U . . .
C21 C 0.2905(3) 0.51139(19) 0.78817(14) 0.0250(6) Uani 1 1 d . . . . .
C22 C 0.1121(3) 0.6735(2) 0.69549(15) 0.0271(7) Uani 1 1 d . . . . .
H22A H 0.080568 0.639139 0.728305 0.032 Uiso 1 1 calc R U . . .
H22B H 0.041907 0.678940 0.656733 0.032 Uiso 1 1 calc R U . . .
C23 C 0.1544(3) 0.7719(2) 0.71989(15) 0.0276(7) Uani 1 1 d . . . . .
H23A H 0.179908 0.808076 0.685954 0.033 Uiso 1 1 calc R U . . .
H23B H 0.083304 0.805703 0.730636 0.033 Uiso 1 1 calc R U . . .
C24 C 0.2300(3) 0.7544(2) 0.82929(15) 0.0273(7) Uani 1 1 d . . . . .
H24 H 0.142485 0.751510 0.827159 0.033 Uiso 1 1 calc R U . . .
C25 C 0.3135(3) 0.7441(2) 0.89116(15) 0.0276(7) Uani 1 1 d . . . . .
C26 C 0.2590(3) 0.7227(2) 0.94153(16) 0.0365(8) Uani 1 1 d . . . . .
H26 H 0.170040 0.717679 0.933439 0.044 Uiso 1 1 calc R U . . .
C27 C 0.3309(4) 0.7091(3) 1.00170(17) 0.0429(9) Uani 1 1 d . . . . .
H27 H 0.292814 0.693295 1.035280 0.051 Uiso 1 1 calc R U . . .
C28 C 0.4594(3) 0.7184(2) 1.01355(16) 0.0395(8) Uani 1 1 d . . . . .
H28 H 0.509988 0.709656 1.055715 0.047 Uiso 1 1 calc R U . . .
C29 C 0.5153(3) 0.7400(2) 0.96556(15) 0.0319(7) Uani 1 1 d . . . . .
H29 H 0.604312 0.746409 0.975008 0.038 Uiso 1 1 calc R U . . .
C30 C 0.4447(3) 0.7530(2) 0.90300(14) 0.0250(6) Uani 1 1 d . . . . .
C31A C 0.1877(6) 0.4791(6) 0.5222(3) 0.0616(15) Uani 0.715(6) 1 d D U P B 3
H31A H 0.157133 0.522849 0.550828 0.074 Uiso 0.715(6) 1 calc R U P B 3
H31B H 0.191854 0.414506 0.540624 0.074 Uiso 0.715(6) 1 calc R U P B 3
Cl1A Cl 0.0837(2) 0.47980(13) 0.44700(8) 0.0684(7) Uani 0.715(6) 1 d D . P B 3
Cl2A Cl 0.3368(3) 0.5138(2) 0.51703(12) 0.0986(14) Uani 0.715(6) 1 d D . P B 3
C31B C 0.2398(13) 0.4625(17) 0.5340(10) 0.080(5) Uani 0.285(6) 1 d D U P B 4
H31C H 0.192267 0.402459 0.532115 0.096 Uiso 0.285(6) 1 calc R U P B 4
H31D H 0.229388 0.498481 0.571665 0.096 Uiso 0.285(6) 1 calc R U P B 4
Cl1B Cl 0.1788(16) 0.5252(9) 0.4685(5) 0.189(8) Uani 0.285(6) 1 d D . P B 4
Cl2B Cl 0.3948(5) 0.4370(8) 0.5436(3) 0.096(3) Uani 0.285(6) 1 d D . P B 4


_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 O4 1.891(2) . ?
Cu1 O5 1.8942(19) . ?
Cu1 N4 1.971(2) . ?
Cu1 N3 1.973(2) . ?
S1 O6 1.421(2) . ?
S1 O7 1.421(2) . ?
S1 N5 1.584(3) . ?
S1 C6 1.762(3) . ?
S2 O8 1.419(2) . ?
S2 O9 1.423(2) . ?
S2 N6 1.587(2) . ?
S2 C21 1.773(3) . ?
O3 N2A 1.248(8) . ?
O3 N2B 1.277(11) . ?
O4 C15 1.306(3) . ?
O5 C30 1.303(3) . ?
N1A N2A 1.23(2) . ?
N1A C1 1.477(15) . ?
N2A C16 1.513(14) . ?
N1B N2B 1.27(3) . ?
N1B C16 1.500(18) . ?
N2B C1 1.52(2) . ?
N3 C9 1.278(3) . ?
N3 C8 1.469(3) . ?
N4 C24 1.278(4) . ?
N4 C23 1.463(4) . ?
N5 C7 1.453(4) . ?
N5 H5N 0.70(3) . ?
N6 C22 1.447(4) . ?
N6 H6N 0.78(3) . ?
C1 C2 1.367(4) . ?
C1 C6 1.381(4) . ?
C2 C3 1.367(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.365(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.362(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.370(4) . ?
C5 H5 0.9500 . ?
C7 C8 1.508(4) . ?
C7 H7A 0.9900 . ?
C7 H7AB 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8AB 0.9900 . ?
C9 C10 1.424(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.405(4) . ?
C10 C15 1.405(4) . ?
C11 C12 1.354(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.388(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.362(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.389(4) . ?
C14 H14 0.9500 . ?
C16 C17 1.365(5) . ?
C16 C21 1.378(4) . ?
C17 C18 1.369(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.362(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.367(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.372(4) . ?
C20 H20 0.9500 . ?
C22 C23 1.515(4) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.428(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.400(4) . ?
C25 C30 1.403(4) . ?
C26 C27 1.357(5) . ?
C26 H26 0.9500 . ?
C27 C28 1.375(5) . ?
C27 H27 0.9500 . ?
C28 C29 1.365(4) . ?
C28 H28 0.9500 . ?
C29 C30 1.393(4) . ?
C29 H29 0.9500 . ?
C31A Cl2A 1.737(7) . ?
C31A Cl1A 1.738(7) . ?
C31A H31A 0.9900 . ?
C31A H31B 0.9900 . ?
C31B Cl1B 1.662(14) . ?
C31B Cl2B 1.699(14) . ?
C31B H31C 0.9900 . ?
C31B H31D 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
O4 Cu1 O5 157.39(8) . . ?
O4 Cu1 N4 90.10(9) . . ?
O5 Cu1 N4 93.09(9) . . ?
O4 Cu1 N3 91.64(9) . . ?
O5 Cu1 N3 93.42(9) . . ?
N4 Cu1 N3 158.66(9) . . ?
O6 S1 O7 120.17(13) . . ?
O6 S1 N5 107.96(13) . . ?
O7 S1 N5 106.75(13) . . ?
O6 S1 C6 105.56(13) . . ?
O7 S1 C6 107.72(13) . . ?
N5 S1 C6 108.21(14) . . ?
O8 S2 O9 120.11(12) . . ?
O8 S2 N6 107.46(13) . . ?
O9 S2 N6 106.87(13) . . ?
O8 S2 C21 107.61(13) . . ?
O9 S2 C21 105.46(13) . . ?
N6 S2 C21 108.98(13) . . ?
C15 O4 Cu1 129.87(18) . . ?
C30 O5 Cu1 128.95(19) . . ?
N2A N1A C1 109.8(11) . . ?
N1A N2A O3 126.7(18) . . ?
N1A N2A C16 107.0(11) . . ?
O3 N2A C16 126.1(10) . . ?
N2B N1B C16 105.7(12) . . ?
N1B N2B O3 126(2) . . ?
N1B N2B C1 105.5(13) . . ?
O3 N2B C1 127.7(12) . . ?
C9 N3 C8 115.4(2) . . ?
C9 N3 Cu1 124.48(19) . . ?
C8 N3 Cu1 119.77(18) . . ?
C24 N4 C23 115.2(2) . . ?
C24 N4 Cu1 123.8(2) . . ?
C23 N4 Cu1 120.76(19) . . ?
C7 N5 S1 121.7(2) . . ?
C7 N5 H5N 119(3) . . ?
S1 N5 H5N 111(3) . . ?
C22 N6 S2 119.3(2) . . ?
C22 N6 H6N 115(2) . . ?
S2 N6 H6N 118(2) . . ?
C2 C1 C6 121.5(3) . . ?
C2 C1 N1A 115.5(3) . . ?
C6 C1 N1A 119.0(3) . . ?
C2 C1 N2B 115.4(4) . . ?
C6 C1 N2B 120.3(4) . . ?
C1 C2 C3 119.7(3) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C4 C3 C2 119.2(3) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C5 C4 C3 121.1(3) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 120.7(3) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C1 117.8(3) . . ?
C5 C6 S1 118.9(2) . . ?
C1 C6 S1 123.2(2) . . ?
N5 C7 C8 111.0(2) . . ?
N5 C7 H7A 109.4 . . ?
C8 C7 H7A 109.4 . . ?
N5 C7 H7AB 109.4 . . ?
C8 C7 H7AB 109.4 . . ?
H7A C7 H7AB 108.0 . . ?
N3 C8 C7 111.9(2) . . ?
N3 C8 H8A 109.2 . . ?
C7 C8 H8A 109.2 . . ?
N3 C8 H8AB 109.2 . . ?
C7 C8 H8AB 109.2 . . ?
H8A C8 H8AB 107.9 . . ?
N3 C9 C10 127.3(3) . . ?
N3 C9 H9 116.3 . . ?
C10 C9 H9 116.3 . . ?
C11 C10 C15 119.3(3) . . ?
C11 C10 C9 118.1(3) . . ?
C15 C10 C9 122.6(3) . . ?
C12 C11 C10 121.3(3) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C11 C12 C13 119.1(3) . . ?
C11 C12 H12 120.5 . . ?
C13 C12 H12 120.5 . . ?
C14 C13 C12 120.9(3) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C13 C14 C15 121.4(3) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 H14 119.3 . . ?
O4 C15 C14 118.9(3) . . ?
O4 C15 C10 123.0(3) . . ?
C14 C15 C10 118.0(3) . . ?
C17 C16 C21 120.9(3) . . ?
C17 C16 N1B 120.4(4) . . ?
C21 C16 N1B 112.2(4) . . ?
C17 C16 N2A 114.6(3) . . ?
C21 C16 N2A 122.7(3) . . ?
C16 C17 C18 119.4(3) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 H17 120.3 . . ?
C19 C18 C17 120.3(3) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C18 C19 C20 120.1(3) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C19 C20 C21 120.4(3) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C20 C21 C16 118.8(3) . . ?
C20 C21 S2 119.1(2) . . ?
C16 C21 S2 122.1(2) . . ?
N6 C22 C23 111.9(2) . . ?
N6 C22 H22A 109.2 . . ?
C23 C22 H22A 109.2 . . ?
N6 C22 H22B 109.2 . . ?
C23 C22 H22B 109.2 . . ?
H22A C22 H22B 107.9 . . ?
N4 C23 C22 111.0(2) . . ?
N4 C23 H23A 109.4 . . ?
C22 C23 H23A 109.4 . . ?
N4 C23 H23B 109.4 . . ?
C22 C23 H23B 109.4 . . ?
H23A C23 H23B 108.0 . . ?
N4 C24 C25 127.1(3) . . ?
N4 C24 H24 116.5 . . ?
C25 C24 H24 116.5 . . ?
C26 C25 C30 119.6(3) . . ?
C26 C25 C24 116.9(3) . . ?
C30 C25 C24 123.5(3) . . ?
C27 C26 C25 121.2(3) . . ?
C27 C26 H26 119.4 . . ?
C25 C26 H26 119.4 . . ?
C26 C27 C28 119.3(3) . . ?
C26 C27 H27 120.4 . . ?
C28 C27 H27 120.4 . . ?
C29 C28 C27 120.9(3) . . ?
C29 C28 H28 119.5 . . ?
C27 C28 H28 119.5 . . ?
C28 C29 C30 121.4(3) . . ?
C28 C29 H29 119.3 . . ?
C30 C29 H29 119.3 . . ?
O5 C30 C29 119.1(3) . . ?
O5 C30 C25 123.3(3) . . ?
C29 C30 C25 117.6(3) . . ?
Cl2A C31A Cl1A 110.3(4) . . ?
Cl2A C31A H31A 109.6 . . ?
Cl1A C31A H31A 109.6 . . ?
Cl2A C31A H31B 109.6 . . ?
Cl1A C31A H31B 109.6 . . ?
H31A C31A H31B 108.1 . . ?
Cl1B C31B Cl2B 113.3(11) . . ?
Cl1B C31B H31C 108.9 . . ?
Cl2B C31B H31C 108.9 . . ?
Cl1B C31B H31D 108.9 . . ?
Cl2B C31B H31D 108.9 . . ?
H31C C31B H31D 107.7 . . ?

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
_geom_hbond_publ_flag
N5 H5N O5 0.70(3) 2.07(3) 2.729(3) 158(4) . yes
N6 H6N O4 0.78(3) 1.97(3) 2.715(3) 160(3) . yes

_refine_diff_density_max         0.445
_refine_diff_density_min         -0.477
_refine_diff_density_rms         0.069



####################################################################### 
# 
# 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_cu_Fei18_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 2088569'
loop_
_audit_author_name
_audit_author_address
'Xavier Ottenwaelder' 'Concordia University'
_audit_update_record             
;
2021-06-07 deposited with the CCDC.	2021-08-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H31 Cu N3 O4 S'
_chemical_formula_sum            'C23 H31 Cu N3 O4 S'
_chemical_formula_weight         509.11

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

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   18.1906(3)
_cell_length_b                   12.7306(2)
_cell_length_c                   10.9264(2)
_cell_angle_alpha                90
_cell_angle_beta                 100.5390(10)
_cell_angle_gamma                90
_cell_volume                     2487.62(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    9860
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      67.31

_exptl_crystal_description       plate
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_F_000             1068
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.188
_exptl_crystal_size_mid          0.146
_exptl_crystal_size_min          0.103
_exptl_absorpt_coefficient_mu    2.293
_shelx_estimated_absorpt_T_min   0.672
_shelx_estimated_absorpt_T_max   0.798
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6466
_exptl_absorpt_correction_T_max  0.7530
_exptl_absorpt_process_details   'SADABS-2016/2 - Bruker AXS'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22219
_diffrn_reflns_av_unetI/netI     0.0415
_diffrn_reflns_av_R_equivalents  0.0492
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.471
_diffrn_reflns_theta_max         68.494
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4524
_reflns_number_gt                3562
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0766P)²+0.8887P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4524
_refine_ls_number_parameters     296
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0636
_refine_ls_R_factor_gt           0.0435
_refine_ls_wR_factor_ref         0.1342
_refine_ls_wR_factor_gt          0.1197
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_restrained_S_all      1.103
_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 0.88680(2) 0.58579(3) 0.44754(4) 0.02427(16) Uani 1 1 d . . . . .
S1 S 1.00011(4) 0.52519(5) 0.28052(7) 0.0252(2) Uani 1 1 d . . . . .
O1 O 0.83713(14) 0.37155(18) 0.4691(2) 0.0490(6) Uani 1 1 d . . . . .
H1A H 0.809286 0.414124 0.497659 0.074 Uiso 1 1 calc R U . . .
O2 O 0.79602(11) 0.56299(15) 0.50887(19) 0.0279(5) Uani 1 1 d . . . . .
O3 O 1.03863(11) 0.56515(16) 0.18652(19) 0.0309(5) Uani 1 1 d . . . . .
O4 O 1.03868(11) 0.44545(16) 0.36449(19) 0.0304(5) Uani 1 1 d . . . . .
N1 N 0.88771(14) 0.42774(17) 0.4089(2) 0.0274(6) Uani 1 1 d . . . . .
H1 H 0.939191 0.400675 0.441380 0.033 Uiso 1 1 calc R U . . .
N2 N 0.97316(13) 0.61511(17) 0.3625(2) 0.0251(5) Uani 1 1 d . . . . .
N3 N 0.87523(13) 0.73601(18) 0.4446(2) 0.0268(6) Uani 1 1 d . . . . .
C1 C 0.87191(17) 0.4107(2) 0.2762(3) 0.0274(7) Uani 1 1 d . . . . .
C2 C 0.80987(18) 0.3559(2) 0.2176(3) 0.0388(8) Uani 1 1 d . . . . .
H2 H 0.775885 0.326823 0.264888 0.047 Uiso 1 1 calc R U . . .
C3 C 0.79743(19) 0.3435(3) 0.0889(3) 0.0439(9) Uani 1 1 d . . . . .
H3 H 0.755113 0.304918 0.048772 0.053 Uiso 1 1 calc R U . . .
C4 C 0.84551(18) 0.3863(3) 0.0193(3) 0.0369(8) Uani 1 1 d . . . . .
H4 H 0.836963 0.375951 -0.068270 0.044 Uiso 1 1 calc R U . . .
C5 C 0.90609(17) 0.4441(2) 0.0763(3) 0.0296(7) Uani 1 1 d . . . . .
H5 H 0.938669 0.475156 0.027880 0.036 Uiso 1 1 calc R U . . .
C6 C 0.91955(16) 0.4570(2) 0.2045(3) 0.0254(6) Uani 1 1 d . . . . .
C7 C 0.96084(17) 0.7199(2) 0.3013(3) 0.0300(7) Uani 1 1 d . . . . .
H7A H 0.922287 0.715467 0.224788 0.036 Uiso 1 1 calc R U . . .
H7AB H 1.007776 0.746696 0.279097 0.036 Uiso 1 1 calc R U . . .
C8 C 0.93511(17) 0.7906(2) 0.3960(3) 0.0316(7) Uani 1 1 d . . . . .
H8A H 0.977305 0.806081 0.464663 0.038 Uiso 1 1 calc R U . . .
H8AB H 0.916215 0.857723 0.356670 0.038 Uiso 1 1 calc R U . . .
C9 C 0.82104(16) 0.7865(2) 0.4771(3) 0.0281(7) Uani 1 1 d . . . . .
H9 H 0.820679 0.860515 0.465748 0.034 Uiso 1 1 calc R U . . .
C10 C 0.76069(16) 0.7427(2) 0.5289(3) 0.0287(7) Uani 1 1 d . . . . .
C11 C 0.75091(15) 0.6336(2) 0.5446(3) 0.0269(6) Uani 1 1 d . . . . .
C12 C 0.68866(17) 0.6000(2) 0.5986(3) 0.0324(7) Uani 1 1 d . . . . .
C13 C 0.64163(17) 0.6771(3) 0.6310(3) 0.0368(8) Uani 1 1 d . . . . .
H13 H 0.600277 0.654596 0.666339 0.044 Uiso 1 1 calc R U . . .
C14 C 0.65045(17) 0.7853(3) 0.6157(3) 0.0335(7) Uani 1 1 d . . . . .
C15 C 0.71032(17) 0.8161(2) 0.5652(3) 0.0333(7) Uani 1 1 d . . . . .
H15 H 0.718408 0.888930 0.554102 0.040 Uiso 1 1 calc R U . . .
C16 C 0.67436(18) 0.4837(3) 0.6216(3) 0.0401(8) Uani 1 1 d . . . . .
C17 C 0.7419(2) 0.4386(3) 0.7116(3) 0.0434(9) Uani 1 1 d . . . . .
H17A H 0.746184 0.473237 0.792743 0.065 Uiso 1 1 calc R U . . .
H17B H 0.787540 0.450932 0.678077 0.065 Uiso 1 1 calc R U . . .
H17C H 0.734917 0.362964 0.721457 0.065 Uiso 1 1 calc R U . . .
C18 C 0.6588(2) 0.4227(3) 0.4977(4) 0.0486(10) Uani 1 1 d . . . . .
H18A H 0.655247 0.347494 0.514831 0.073 Uiso 1 1 calc R U . . .
H18B H 0.699699 0.434780 0.452107 0.073 Uiso 1 1 calc R U . . .
H18C H 0.611681 0.447024 0.447534 0.073 Uiso 1 1 calc R U . . .
C19 C 0.6059(2) 0.4669(3) 0.6842(5) 0.0667(13) Uani 1 1 d . . . . .
H19A H 0.599311 0.391619 0.697573 0.100 Uiso 1 1 calc R U . . .
H19B H 0.561149 0.494863 0.630451 0.100 Uiso 1 1 calc R U . . .
H19C H 0.613811 0.503472 0.764477 0.100 Uiso 1 1 calc R U . . .
C20 C 0.59317(19) 0.8614(3) 0.6538(3) 0.0413(8) Uani 1 1 d . . . . .
C21 C 0.6202(2) 0.9758(3) 0.6518(4) 0.0578(11) Uani 1 1 d . . . . .
H21A H 0.583897 1.022421 0.680417 0.087 Uiso 1 1 calc R U . . .
H21B H 0.624944 0.995030 0.566742 0.087 Uiso 1 1 calc R U . . .
H21C H 0.668849 0.982921 0.706953 0.087 Uiso 1 1 calc R U . . .
C22 C 0.5815(2) 0.8362(3) 0.7863(3) 0.0483(9) Uani 1 1 d . . . . .
H22A H 0.629400 0.840824 0.844019 0.072 Uiso 1 1 calc R U . . .
H22B H 0.561285 0.764957 0.788506 0.072 Uiso 1 1 calc R U . . .
H22C H 0.546207 0.886662 0.811026 0.072 Uiso 1 1 calc R U . . .
C23 C 0.5190(2) 0.8500(3) 0.5628(4) 0.0568(11) Uani 1 1 d . . . . .
H23A H 0.501567 0.777160 0.563279 0.085 Uiso 1 1 calc R U . . .
H23B H 0.526119 0.868671 0.478728 0.085 Uiso 1 1 calc R U . . .
H23C H 0.481669 0.896840 0.588001 0.085 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 O2 1.915(2) . ?
Cu1 N3 1.924(2) . ?
Cu1 N2 2.001(2) . ?
Cu1 N1 2.057(2) . ?
Cu1 O4 2.279(2) 3_766 ?
S1 O3 1.438(2) . ?
S1 O4 1.459(2) . ?
S1 N2 1.585(2) . ?
S1 C6 1.774(3) . ?
O1 N1 1.418(3) . ?
O1 H1A 0.8400 . ?
O2 C11 1.323(3) . ?
N1 C1 1.442(4) . ?
N1 H1 1.0000 . ?
N2 C7 1.490(4) . ?
N3 C9 1.280(4) . ?
N3 C8 1.470(4) . ?
C1 C2 1.380(4) . ?
C1 C6 1.400(4) . ?
C2 C3 1.392(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.373(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.376(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.387(4) . ?
C5 H5 0.9500 . ?
C7 C8 1.509(4) . ?
C7 H7A 0.9900 . ?
C7 H7AB 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8AB 0.9900 . ?
C9 C10 1.437(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.415(4) . ?
C10 C15 1.415(4) . ?
C11 C12 1.435(4) . ?
C12 C13 1.390(4) . ?
C12 C16 1.531(4) . ?
C13 C14 1.401(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.365(4) . ?
C14 C20 1.535(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.538(5) . ?
C16 C18 1.541(5) . ?
C16 C19 1.542(5) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C23 1.530(5) . ?
C20 C22 1.536(5) . ?
C20 C21 1.539(5) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 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
O2 Cu1 N3 93.31(9) . . ?
O2 Cu1 N2 172.50(9) . . ?
N3 Cu1 N2 84.25(9) . . ?
O2 Cu1 N1 87.90(9) . . ?
N3 Cu1 N1 166.97(10) . . ?
N2 Cu1 N1 92.90(9) . . ?
O2 Cu1 O4 93.84(8) . 3_766 ?
N3 Cu1 O4 103.51(9) . 3_766 ?
N2 Cu1 O4 93.62(9) . 3_766 ?
N1 Cu1 O4 89.34(9) . 3_766 ?
O3 S1 O4 117.01(12) . . ?
O3 S1 N2 112.92(12) . . ?
O4 S1 N2 108.07(12) . . ?
O3 S1 C6 107.90(13) . . ?
O4 S1 C6 102.42(13) . . ?
N2 S1 C6 107.68(13) . . ?
N1 O1 H1A 109.5 . . ?
C11 O2 Cu1 128.43(18) . . ?
S1 O4 Cu1 145.72(13) . 3_766 ?
O1 N1 C1 111.3(2) . . ?
O1 N1 Cu1 111.59(17) . . ?
C1 N1 Cu1 110.26(17) . . ?
O1 N1 H1 107.8 . . ?
C1 N1 H1 107.8 . . ?
Cu1 N1 H1 107.8 . . ?
C7 N2 S1 115.47(19) . . ?
C7 N2 Cu1 107.98(17) . . ?
S1 N2 Cu1 118.54(13) . . ?
C9 N3 C8 121.4(2) . . ?
C9 N3 Cu1 125.6(2) . . ?
C8 N3 Cu1 112.92(17) . . ?
C2 C1 C6 119.4(3) . . ?
C2 C1 N1 122.5(3) . . ?
C6 C1 N1 118.0(3) . . ?
C1 C2 C3 119.6(3) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C4 C3 C2 120.8(3) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 120.0(3) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 120.0(3) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C1 120.1(3) . . ?
C5 C6 S1 120.6(2) . . ?
C1 C6 S1 119.1(2) . . ?
N2 C7 C8 105.5(2) . . ?
N2 C7 H7A 110.7 . . ?
C8 C7 H7A 110.7 . . ?
N2 C7 H7AB 110.7 . . ?
C8 C7 H7AB 110.7 . . ?
H7A C7 H7AB 108.8 . . ?
N3 C8 C7 108.0(2) . . ?
N3 C8 H8A 110.1 . . ?
C7 C8 H8A 110.1 . . ?
N3 C8 H8AB 110.1 . . ?
C7 C8 H8AB 110.1 . . ?
H8A C8 H8AB 108.4 . . ?
N3 C9 C10 126.6(3) . . ?
N3 C9 H9 116.7 . . ?
C10 C9 H9 116.7 . . ?
C11 C10 C15 120.8(3) . . ?
C11 C10 C9 123.4(3) . . ?
C15 C10 C9 115.7(3) . . ?
O2 C11 C10 122.2(3) . . ?
O2 C11 C12 119.9(3) . . ?
C10 C11 C12 117.9(3) . . ?
C13 C12 C11 117.6(3) . . ?
C13 C12 C16 120.6(3) . . ?
C11 C12 C16 121.7(3) . . ?
C12 C13 C14 125.1(3) . . ?
C12 C13 H13 117.5 . . ?
C14 C13 H13 117.5 . . ?
C15 C14 C13 116.6(3) . . ?
C15 C14 C20 124.0(3) . . ?
C13 C14 C20 119.3(3) . . ?
C14 C15 C10 121.9(3) . . ?
C14 C15 H15 119.1 . . ?
C10 C15 H15 119.1 . . ?
C12 C16 C17 109.0(3) . . ?
C12 C16 C18 110.7(3) . . ?
C17 C16 C18 111.7(3) . . ?
C12 C16 C19 112.5(3) . . ?
C17 C16 C19 106.2(3) . . ?
C18 C16 C19 106.6(3) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C23 C20 C14 109.0(3) . . ?
C23 C20 C22 109.6(3) . . ?
C14 C20 C22 110.0(3) . . ?
C23 C20 C21 109.1(3) . . ?
C14 C20 C21 111.1(3) . . ?
C22 C20 C21 108.1(3) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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
_geom_hbond_publ_flag
N1 H1 N2 1.00 2.43 3.261(4) 139.5 3_766 yes
N1 H1 O4 1.00 2.21 2.884(3) 123.8 . yes
O1 H1A O2 0.84 1.92 2.609(3) 138.9 . yes

_refine_diff_density_max         0.712
_refine_diff_density_min         -0.838
_refine_diff_density_rms         0.103



####################################################################### 
# 
# 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_Hardeep5_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2088566'
loop_
_audit_author_name
_audit_author_address
'Xavier Ottenwaelder' 'Concordia University'
_audit_update_record             
;
2021-06-07 deposited with the CCDC.	2021-08-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H30 Cu2 N6 O8 S2'
_chemical_formula_sum            'C30 H30 Cu2 N6 O8 S2'
_chemical_formula_weight         793.80

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

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.2868(12)
_cell_length_b                   9.6560(10)
_cell_length_c                   14.3063(15)
_cell_angle_alpha                90
_cell_angle_beta                 94.4720(10)
_cell_angle_gamma                90
_cell_volume                     1554.4(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2772
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      23.53

_exptl_crystal_description       rhomb
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.696
_exptl_crystal_F_000             812
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.171
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.092
_exptl_absorpt_coefficient_mu    1.565
_shelx_estimated_absorpt_T_min   0.776
_shelx_estimated_absorpt_T_max   0.869
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7143
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS-2016/2 - Bruker AXS area'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15265
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_av_R_equivalents  0.0565
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.810
_diffrn_reflns_theta_max         25.341
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2830
_reflns_number_gt                2329
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0332P)²+0.8823P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2830
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0328
_refine_ls_wR_factor_ref         0.0787
_refine_ls_wR_factor_gt          0.0736
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_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 0.19929(3) 0.51896(3) 0.49447(2) 0.01633(12) Uani 1 1 d . . . . .
S1 S 0.00169(6) 0.67640(8) 0.38154(5) 0.02114(19) Uani 1 1 d . . . . .
O1 O 0.18343(19) 0.6852(2) 0.66339(14) 0.0288(5) Uani 1 1 d . . . . .
H1 H 0.234300 0.622008 0.671686 0.043 Uiso 1 1 calc R U . . .
O2 O 0.31579(17) 0.4987(2) 0.59816(14) 0.0224(5) Uani 1 1 d . . . . .
O3 O -0.08173(17) 0.6475(2) 0.45137(14) 0.0240(5) Uani 1 1 d . . . . .
O4 O -0.04705(18) 0.7144(2) 0.28902(14) 0.0307(5) Uani 1 1 d . . . . .
N1 N 0.1295(2) 0.6778(2) 0.57025(16) 0.0183(5) Uani 1 1 d . . . . .
H1A H 0.043039 0.658360 0.574249 0.022 Uiso 1 1 calc R U . . .
N2 N 0.0903(2) 0.5500(2) 0.38052(16) 0.0189(5) Uani 1 1 d . . . . .
N3 N 0.2942(2) 0.4175(2) 0.41026(16) 0.0183(5) Uani 1 1 d . . . . .
C1 C 0.1395(2) 0.8078(3) 0.5213(2) 0.0208(7) Uani 1 1 d . . . . .
C2 C 0.2064(3) 0.9171(3) 0.5585(2) 0.0252(7) Uani 1 1 d . . . . .
H2 H 0.245989 0.909746 0.619443 0.030 Uiso 1 1 calc R U . . .
C3 C 0.2159(3) 1.0378(3) 0.5068(3) 0.0353(9) Uani 1 1 d . . . . .
H3 H 0.260772 1.113423 0.533286 0.042 Uiso 1 1 calc R U . . .
C4 C 0.1607(3) 1.0495(3) 0.4172(3) 0.0349(9) Uani 1 1 d . . . . .
H4 H 0.167267 1.132701 0.382502 0.042 Uiso 1 1 calc R U . . .
C5 C 0.0960(3) 0.9393(3) 0.3786(2) 0.0282(8) Uani 1 1 d . . . . .
H5 H 0.059356 0.946138 0.316694 0.034 Uiso 1 1 calc R U . . .
C6 C 0.0845(2) 0.8190(3) 0.4296(2) 0.0206(7) Uani 1 1 d . . . . .
C7 C 0.1655(3) 0.5473(3) 0.2997(2) 0.0234(7) Uani 1 1 d . . . . .
H7A H 0.214396 0.632389 0.298811 0.028 Uiso 1 1 calc R U . . .
H7AB H 0.115223 0.541455 0.239991 0.028 Uiso 1 1 calc R U . . .
C8 C 0.2442(3) 0.4212(3) 0.3121(2) 0.0234(7) Uani 1 1 d . . . . .
H8A H 0.197340 0.336229 0.297257 0.028 Uiso 1 1 calc R U . . .
H8AB H 0.308990 0.426195 0.269412 0.028 Uiso 1 1 calc R U . . .
C9 C 0.3897(3) 0.3505(3) 0.4337(2) 0.0206(7) Uani 1 1 d . . . . .
H9 H 0.429775 0.308789 0.384951 0.025 Uiso 1 1 calc R U . . .
C10 C 0.4414(2) 0.3335(3) 0.5286(2) 0.0199(7) Uani 1 1 d . . . . .
C11 C 0.5361(3) 0.2378(3) 0.5432(2) 0.0300(8) Uani 1 1 d . . . . .
H11 H 0.564712 0.191777 0.490738 0.036 Uiso 1 1 calc R U . . .
C12 C 0.5874(3) 0.2101(4) 0.6314(2) 0.0349(8) Uani 1 1 d . . . . .
H12 H 0.649584 0.143894 0.640380 0.042 Uiso 1 1 calc R U . . .
C13 C 0.5469(3) 0.2805(3) 0.7073(2) 0.0309(8) Uani 1 1 d . . . . .
H13 H 0.582225 0.262387 0.768493 0.037 Uiso 1 1 calc R U . . .
C14 C 0.4566(3) 0.3759(3) 0.6957(2) 0.0270(7) Uani 1 1 d . . . . .
H14 H 0.431311 0.423090 0.748893 0.032 Uiso 1 1 calc R U . . .
C15 C 0.4009(2) 0.4051(3) 0.6060(2) 0.0192(6) Uani 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 O2 1.9141(19) . ?
Cu1 N3 1.939(2) . ?
Cu1 N2 1.987(2) . ?
Cu1 N1 2.069(2) . ?
Cu1 O3 2.2592(19) 3_566 ?
S1 O4 1.441(2) . ?
S1 O3 1.452(2) . ?
S1 N2 1.579(2) . ?
S1 C6 1.773(3) . ?
O1 N1 1.423(3) . ?
O1 H1 0.8400 . ?
O2 C15 1.317(3) . ?
N1 C1 1.446(4) . ?
N1 H1A 1.0000 . ?
N2 C7 1.487(4) . ?
N3 C9 1.279(4) . ?
N3 C8 1.472(4) . ?
C1 C2 1.380(4) . ?
C1 C6 1.412(4) . ?
C2 C3 1.389(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.387(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.380(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.383(4) . ?
C5 H5 0.9500 . ?
C7 C8 1.510(4) . ?
C7 H7A 0.9900 . ?
C7 H7AB 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8AB 0.9900 . ?
C9 C10 1.445(4) . ?
C9 H9 0.9500 . ?
C10 C15 1.412(4) . ?
C10 C11 1.416(4) . ?
C11 C12 1.374(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.389(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.373(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.412(4) . ?
C14 H14 0.9500 . ?

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
O2 Cu1 N3 92.90(9) . . ?
O2 Cu1 N2 174.40(9) . . ?
N3 Cu1 N2 84.44(10) . . ?
O2 Cu1 N1 86.34(8) . . ?
N3 Cu1 N1 162.07(10) . . ?
N2 Cu1 N1 94.68(9) . . ?
O2 Cu1 O3 92.74(8) . 3_566 ?
N3 Cu1 O3 102.78(9) . 3_566 ?
N2 Cu1 O3 92.64(8) . 3_566 ?
N1 Cu1 O3 95.15(9) . 3_566 ?
O4 S1 O3 117.35(13) . . ?
O4 S1 N2 112.65(13) . . ?
O3 S1 N2 107.63(12) . . ?
O4 S1 C6 108.09(14) . . ?
O3 S1 C6 103.48(13) . . ?
N2 S1 C6 106.80(13) . . ?
N1 O1 H1 109.5 . . ?
C15 O2 Cu1 126.06(18) . . ?
S1 O3 Cu1 143.36(13) . 3_566 ?
O1 N1 C1 111.5(2) . . ?
O1 N1 Cu1 112.06(15) . . ?
C1 N1 Cu1 110.03(17) . . ?
O1 N1 H1A 107.7 . . ?
C1 N1 H1A 107.7 . . ?
Cu1 N1 H1A 107.7 . . ?
C7 N2 S1 114.91(19) . . ?
C7 N2 Cu1 106.31(17) . . ?
S1 N2 Cu1 117.46(13) . . ?
C9 N3 C8 121.0(2) . . ?
C9 N3 Cu1 126.0(2) . . ?
C8 N3 Cu1 113.03(18) . . ?
C2 C1 C6 119.2(3) . . ?
C2 C1 N1 122.5(3) . . ?
C6 C1 N1 118.1(3) . . ?
C1 C2 C3 119.9(3) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C4 C3 C2 120.9(3) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C5 C4 C3 119.5(3) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 120.3(3) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C1 120.1(3) . . ?
C5 C6 S1 121.1(2) . . ?
C1 C6 S1 118.8(2) . . ?
N2 C7 C8 106.8(2) . . ?
N2 C7 H7A 110.4 . . ?
C8 C7 H7A 110.4 . . ?
N2 C7 H7AB 110.4 . . ?
C8 C7 H7AB 110.4 . . ?
H7A C7 H7AB 108.6 . . ?
N3 C8 C7 108.1(2) . . ?
N3 C8 H8A 110.1 . . ?
C7 C8 H8A 110.1 . . ?
N3 C8 H8AB 110.1 . . ?
C7 C8 H8AB 110.1 . . ?
H8A C8 H8AB 108.4 . . ?
N3 C9 C10 125.0(3) . . ?
N3 C9 H9 117.5 . . ?
C10 C9 H9 117.5 . . ?
C15 C10 C11 119.5(3) . . ?
C15 C10 C9 123.4(3) . . ?
C11 C10 C9 117.2(3) . . ?
C12 C11 C10 121.5(3) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C11 C12 C13 118.8(3) . . ?
C11 C12 H12 120.6 . . ?
C13 C12 H12 120.6 . . ?
C14 C13 C12 121.4(3) . . ?
C14 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C13 C14 C15 121.2(3) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
O2 C15 C10 123.2(3) . . ?
O2 C15 C14 119.0(3) . . ?
C10 C15 C14 117.8(3) . . ?

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
_geom_hbond_publ_flag
O1 H1 O2 0.84 1.88 2.562(3) 137.8 . yes
N1 H1A O3 1.00 2.17 2.834(3) 122.6 . yes
N1 H1A N2 1.00 2.62 3.430(3) 137.7 3_566 yes

_refine_diff_density_max         0.373
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.074



####################################################################### 
# 
# 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_Hardeep2b_0m
_database_code_depnum_ccdc_archive 'CCDC 2088568'
loop_
_audit_author_name
_audit_author_address
'Xavier Ottenwaelder' 'Concordia University'
_audit_update_record             
;
2021-06-07 deposited with the CCDC.	2021-08-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H31 N3 Ni O4 S'
_chemical_formula_sum            'C23 H31 N3 Ni O4 S'
_chemical_formula_weight         504.28

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 '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           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   16.4967(19)
_cell_length_b                   12.7673(15)
_cell_length_c                   11.5945(14)
_cell_angle_alpha                90
_cell_angle_beta                 107.073(2)
_cell_angle_gamma                90
_cell_volume                     2334.4(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4638
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      24.05

_exptl_crystal_description       plate
_exptl_crystal_colour            bronze
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_F_000             1064
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.272
_exptl_crystal_size_mid          0.199
_exptl_crystal_size_min          0.049
_exptl_absorpt_coefficient_mu    0.955
_shelx_estimated_absorpt_T_min   0.781
_shelx_estimated_absorpt_T_max   0.955
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.641389
_exptl_absorpt_correction_T_max  0.745210
_exptl_absorpt_process_details   'TWINABS 2012/1 - Bruker AXS'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7103
_diffrn_reflns_av_unetI/netI     0.0669
_diffrn_reflns_av_R_equivalents  0.0819
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.291
_diffrn_reflns_theta_max         25.379
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7103
_reflns_number_gt                5748
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 _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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Refined as a 2-component perfect twin. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1160P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7103
_refine_ls_number_parameters     296
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0795
_refine_ls_R_factor_gt           0.0627
_refine_ls_wR_factor_ref         0.1654
_refine_ls_wR_factor_gt          0.1540
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_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
Ni1 Ni 0.65978(4) 0.61856(4) 0.31895(5) 0.0116(2) Uani 1 1 d . . . . .
S1 S 0.57742(8) 0.73220(9) 0.48597(10) 0.0147(3) Uani 1 1 d . . . . .
O1 O 0.8271(2) 0.6840(3) 0.4516(3) 0.0285(9) Uani 1 1 d . . . . .
H1 H 0.829939 0.644461 0.397184 0.043 Uiso 1 1 calc R U . . .
O2 O 0.7503(2) 0.5785(2) 0.2658(3) 0.0136(7) Uani 1 1 d . . . . .
O3 O 0.5024(2) 0.7325(3) 0.5251(3) 0.0190(8) Uani 1 1 d . . . . .
O4 O 0.6127(2) 0.8326(2) 0.4681(3) 0.0198(8) Uani 1 1 d . . . . .
N1 N 0.7420(2) 0.6888(3) 0.4557(4) 0.0152(9) Uani 1 1 d . . . . .
H1A H 0.726339 0.763057 0.451477 0.018 Uiso 1 1 calc R U . . .
N2 N 0.5652(2) 0.6645(3) 0.3672(4) 0.0148(9) Uani 1 1 d . . . . .
N3 N 0.5814(2) 0.5392(3) 0.2077(3) 0.0110(8) Uani 1 1 d . . . . .
C1 C 0.7356(3) 0.6497(4) 0.5703(4) 0.0148(11) Uani 1 1 d . . . . .
C2 C 0.7998(3) 0.5954(4) 0.6506(5) 0.0172(11) Uani 1 1 d . . . . .
H2 H 0.850387 0.582214 0.632993 0.021 Uiso 1 1 calc R U . . .
C3 C 0.7885(3) 0.5606(4) 0.7576(5) 0.0213(12) Uani 1 1 d . . . . .
H3 H 0.831903 0.523434 0.811362 0.026 Uiso 1 1 calc R U . . .
C4 C 0.7139(3) 0.5795(4) 0.7874(4) 0.0183(11) Uani 1 1 d . . . . .
H4 H 0.707630 0.556175 0.860214 0.022 Uiso 1 1 calc R U . . .
C5 C 0.6488(3) 0.6346(4) 0.7051(5) 0.0163(11) Uani 1 1 d . . . . .
H5 H 0.598450 0.648480 0.722908 0.020 Uiso 1 1 calc R U . . .
C6 C 0.6595(3) 0.6681(3) 0.5976(4) 0.0141(10) Uani 1 1 d . . . . .
C7 C 0.4978(3) 0.5840(4) 0.3370(5) 0.0169(11) Uani 1 1 d . . . . .
H7A H 0.444292 0.612196 0.341816 0.020 Uiso 1 1 calc R U . . .
H7AB H 0.513090 0.523912 0.390095 0.020 Uiso 1 1 calc R U . . .
C8 C 0.4930(3) 0.5553(4) 0.2087(4) 0.0153(11) Uani 1 1 d . . . . .
H8A H 0.460187 0.491810 0.184473 0.018 Uiso 1 1 calc R U . . .
H8AB H 0.466696 0.611237 0.153833 0.018 Uiso 1 1 calc R U . . .
C9 C 0.5983(3) 0.4696(3) 0.1373(4) 0.0123(10) Uani 1 1 d . . . . .
H9 H 0.553172 0.429932 0.090847 0.015 Uiso 1 1 calc R U . . .
C10 C 0.6799(3) 0.4482(3) 0.1248(4) 0.0122(10) Uani 1 1 d . . . . .
C11 C 0.6853(3) 0.3629(3) 0.0485(4) 0.0139(10) Uani 1 1 d . . . . .
H11 H 0.636843 0.323958 0.012648 0.017 Uiso 1 1 calc R U . . .
C12 C 0.7594(3) 0.3367(4) 0.0265(4) 0.0132(10) Uani 1 1 d . . . . .
C13 C 0.8305(3) 0.4013(4) 0.0791(4) 0.0141(10) Uani 1 1 d . . . . .
H13 H 0.880570 0.387277 0.060548 0.017 Uiso 1 1 calc R U . . .
C14 C 0.8303(3) 0.4844(3) 0.1569(4) 0.0121(10) Uani 1 1 d . . . . .
C15 C 0.7536(3) 0.5061(3) 0.1839(4) 0.0116(10) Uani 1 1 d . . . . .
C16 C 0.7699(3) 0.2399(4) -0.0460(4) 0.0180(11) Uani 1 1 d . . . . .
C17 C 0.6884(4) 0.1754(4) -0.0853(5) 0.0322(14) Uani 1 1 d . . . . .
H17A H 0.697718 0.113982 -0.127538 0.048 Uiso 1 1 calc R U . . .
H17B H 0.643967 0.216662 -0.137636 0.048 Uiso 1 1 calc R U . . .
H17C H 0.672205 0.154848 -0.015508 0.048 Uiso 1 1 calc R U . . .
C18 C 0.7946(4) 0.2726(4) -0.1578(5) 0.0342(15) Uani 1 1 d . . . . .
H18A H 0.800147 0.211460 -0.203007 0.051 Uiso 1 1 calc R U . . .
H18B H 0.847700 0.309415 -0.133507 0.051 Uiso 1 1 calc R U . . .
H18C H 0.751593 0.317583 -0.207030 0.051 Uiso 1 1 calc R U . . .
C19 C 0.8395(4) 0.1693(4) 0.0337(5) 0.0315(15) Uani 1 1 d . . . . .
H19A H 0.844879 0.107335 -0.010312 0.047 Uiso 1 1 calc R U . . .
H19B H 0.824594 0.150039 0.104944 0.047 Uiso 1 1 calc R U . . .
H19C H 0.892397 0.206458 0.056342 0.047 Uiso 1 1 calc R U . . .
C20 C 0.9126(3) 0.5447(4) 0.2157(4) 0.0139(10) Uani 1 1 d . . . . .
C21 C 0.8993(3) 0.6643(4) 0.1985(5) 0.0193(11) Uani 1 1 d . . . . .
H21A H 0.949950 0.700206 0.242985 0.029 Uiso 1 1 calc R U . . .
H21B H 0.852963 0.685675 0.227458 0.029 Uiso 1 1 calc R U . . .
H21C H 0.886643 0.681236 0.114408 0.029 Uiso 1 1 calc R U . . .
C22 C 0.9460(3) 0.5158(4) 0.3490(4) 0.0218(12) Uani 1 1 d . . . . .
H22A H 0.994786 0.557729 0.387004 0.033 Uiso 1 1 calc R U . . .
H22B H 0.961426 0.443036 0.356566 0.033 Uiso 1 1 calc R U . . .
H22C H 0.902613 0.528286 0.387410 0.033 Uiso 1 1 calc R U . . .
C23 C 0.9832(3) 0.5176(4) 0.1597(5) 0.0240(13) Uani 1 1 d . . . . .
H23A H 1.032458 0.559174 0.196792 0.036 Uiso 1 1 calc R U . . .
H23B H 0.964252 0.531805 0.074667 0.036 Uiso 1 1 calc R U . . .
H23C H 0.997281 0.444664 0.172462 0.036 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
Ni1 N3 1.839(4) . ?
Ni1 O2 1.847(3) . ?
Ni1 N2 1.899(4) . ?
Ni1 N1 1.974(4) . ?
S1 O3 1.438(3) . ?
S1 O4 1.447(3) . ?
S1 N2 1.588(4) . ?
S1 C6 1.775(5) . ?
O1 N1 1.419(5) . ?
O1 H1 0.8200 . ?
O2 C15 1.338(5) . ?
N1 C1 1.452(6) . ?
N1 H1A 0.9800 . ?
N2 C7 1.478(6) . ?
N3 C9 1.291(6) . ?
N3 C8 1.476(6) . ?
C1 C2 1.375(7) . ?
C1 C6 1.402(7) . ?
C2 C3 1.382(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.392(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.399(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.377(7) . ?
C5 H5 0.9300 . ?
C7 C8 1.511(7) . ?
C7 H7A 0.9700 . ?
C7 H7AB 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8AB 0.9700 . ?
C9 C10 1.423(6) . ?
C9 H9 0.9300 . ?
C10 C15 1.416(6) . ?
C10 C11 1.421(6) . ?
C11 C12 1.362(7) . ?
C11 H11 0.9300 . ?
C12 C13 1.417(7) . ?
C12 C16 1.532(6) . ?
C13 C14 1.393(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.418(6) . ?
C14 C20 1.536(6) . ?
C16 C18 1.527(7) . ?
C16 C17 1.528(7) . ?
C16 C19 1.537(7) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C22 1.526(7) . ?
C20 C23 1.530(6) . ?
C20 C21 1.547(6) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 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
N3 Ni1 O2 94.83(15) . . ?
N3 Ni1 N2 84.68(16) . . ?
O2 Ni1 N2 177.16(15) . . ?
N3 Ni1 N1 171.72(16) . . ?
O2 Ni1 N1 87.80(14) . . ?
N2 Ni1 N1 93.07(16) . . ?
O3 S1 O4 117.5(2) . . ?
O3 S1 N2 111.9(2) . . ?
O4 S1 N2 108.2(2) . . ?
O3 S1 C6 108.3(2) . . ?
O4 S1 C6 105.1(2) . . ?
N2 S1 C6 104.9(2) . . ?
N1 O1 H1 109.5 . . ?
C15 O2 Ni1 129.3(3) . . ?
O1 N1 C1 110.8(4) . . ?
O1 N1 Ni1 114.0(3) . . ?
C1 N1 Ni1 111.2(3) . . ?
O1 N1 H1A 106.8 . . ?
C1 N1 H1A 106.8 . . ?
Ni1 N1 H1A 106.8 . . ?
C7 N2 S1 118.6(3) . . ?
C7 N2 Ni1 110.0(3) . . ?
S1 N2 Ni1 121.1(2) . . ?
C9 N3 C8 119.8(4) . . ?
C9 N3 Ni1 125.8(3) . . ?
C8 N3 Ni1 114.2(3) . . ?
C2 C1 C6 119.7(4) . . ?
C2 C1 N1 122.9(4) . . ?
C6 C1 N1 117.4(4) . . ?
C1 C2 C3 119.3(5) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C2 C3 C4 122.0(5) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 H3 119.0 . . ?
C3 C4 C5 118.4(5) . . ?
C3 C4 H4 120.8 . . ?
C5 C4 H4 120.8 . . ?
C6 C5 C4 119.8(5) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C5 C6 C1 120.9(5) . . ?
C5 C6 S1 122.0(4) . . ?
C1 C6 S1 117.0(4) . . ?
N2 C7 C8 102.7(4) . . ?
N2 C7 H7A 111.2 . . ?
C8 C7 H7A 111.2 . . ?
N2 C7 H7AB 111.2 . . ?
C8 C7 H7AB 111.2 . . ?
H7A C7 H7AB 109.1 . . ?
N3 C8 C7 106.0(4) . . ?
N3 C8 H8A 110.5 . . ?
C7 C8 H8A 110.5 . . ?
N3 C8 H8AB 110.5 . . ?
C7 C8 H8AB 110.5 . . ?
H8A C8 H8AB 108.7 . . ?
N3 C9 C10 125.7(4) . . ?
N3 C9 H9 117.2 . . ?
C10 C9 H9 117.2 . . ?
C15 C10 C11 120.0(4) . . ?
C15 C10 C9 123.6(4) . . ?
C11 C10 C9 116.4(4) . . ?
C12 C11 C10 121.9(4) . . ?
C12 C11 H11 119.0 . . ?
C10 C11 H11 119.0 . . ?
C11 C12 C13 116.8(4) . . ?
C11 C12 C16 123.6(4) . . ?
C13 C12 C16 119.6(4) . . ?
C14 C13 C12 124.3(4) . . ?
C14 C13 H13 117.9 . . ?
C12 C13 H13 117.9 . . ?
C13 C14 C15 117.6(4) . . ?
C13 C14 C20 120.0(4) . . ?
C15 C14 C20 122.3(4) . . ?
O2 C15 C10 119.8(4) . . ?
O2 C15 C14 121.1(4) . . ?
C10 C15 C14 119.1(4) . . ?
C18 C16 C17 109.0(5) . . ?
C18 C16 C12 110.3(4) . . ?
C17 C16 C12 111.6(4) . . ?
C18 C16 C19 109.4(4) . . ?
C17 C16 C19 107.4(4) . . ?
C12 C16 C19 109.1(4) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C22 C20 C23 106.4(4) . . ?
C22 C20 C14 109.7(4) . . ?
C23 C20 C14 112.4(4) . . ?
C22 C20 C21 111.4(4) . . ?
C23 C20 C21 105.4(4) . . ?
C14 C20 C21 111.3(4) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

_refine_diff_density_max         1.121
_refine_diff_density_min         -0.675
_refine_diff_density_rms         0.142



####################################################################### 
# 
# 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_Hardeep3FEb_0m
_database_code_depnum_ccdc_archive 'CCDC 2088567'
loop_
_audit_author_name
_audit_author_address
'Xavier Ottenwaelder' 'Concordia University'
_audit_update_record             
;
2021-06-07 deposited with the CCDC.	2021-08-02 downloaded from the CCDC.
;

_vrf_THETM01_Hardeep3FEb_0m      
;
RESPONSE: The crystals did not diffract at high angles
in this room-temperature experiment, and the high-angle 
data was not collected. This sample is, however, isostructural 
to the nickel complex, which was determined in better conditions.
;

_vrf_PLAT023_Hardeep3FEb_0m      
;
RESPONSE: The crystals did not diffract at high angles
in this room-temperature experiment, and the high-angle 
data was not collected. This sample is, however, isostructural 
to the nickel complex, which was determined in better conditions.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H15 N3 O4 S Zn'
_chemical_formula_sum            'C15 H15 N3 O4 S Zn'
_chemical_formula_weight         398.73

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'
Zn Zn -1.5491 0.6778 '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      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

_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+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'

_cell_length_a                   15.0116(7)
_cell_length_b                   15.0137(9)
_cell_length_c                   13.9214(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3137.6(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    6944
_cell_measurement_theta_min      3.18
_cell_measurement_theta_max      53.86

_exptl_crystal_description       rhomb
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.688
_exptl_crystal_F_000             1632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    3.660
_shelx_estimated_absorpt_T_min   0.406
_shelx_estimated_absorpt_T_max   0.711
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6498
_exptl_absorpt_correction_T_max  0.7507
_exptl_absorpt_process_details   
; 
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., 
 J. Appl. Cryst. 48 (2015) 3-10 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            39134
_diffrn_reflns_av_unetI/netI     0.0445
_diffrn_reflns_av_R_equivalents  0.0995
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.943
_diffrn_reflns_theta_max         54.049
_diffrn_reflns_theta_full        54.049
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1934
_reflns_number_gt                1714
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Refined as a 2-component twin. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0822P)²+5.6357P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1934
_refine_ls_number_parameters     229
_refine_ls_number_restraints     37
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0500
_refine_ls_wR_factor_ref         0.1396
_refine_ls_wR_factor_gt          0.1329
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.078
_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
Zn1 Zn 0.46780(8) 0.33038(7) 0.62900(7) 0.0474(4) Uani 1 1 d . . . . .
S1 S 0.35792(15) 0.15933(12) 0.64493(12) 0.0434(5) Uani 1 1 d . . . . .
O1 O 0.6335(3) 0.2456(3) 0.5881(4) 0.0496(13) Uani 1 1 d . . . . .
H1 H 0.641374 0.298995 0.597229 0.074 Uiso 1 1 calc DR U . . .
O2 O 0.5697(3) 0.3971(3) 0.6155(3) 0.0390(13) Uani 1 1 d D . . . .
O3 O 0.2675(5) 0.1297(5) 0.6295(4) 0.073(2) Uani 1 1 d . . . . .
O4 O 0.4045(4) 0.1191(3) 0.7248(3) 0.0552(15) Uani 1 1 d . . . . .
N1 N 0.5434(4) 0.2235(4) 0.6086(4) 0.0303(14) Uani 1 1 d . . . . .
H1N H 0.542718 0.188759 0.668211 0.036 Uiso 1 1 calc R U . . .
N2 N 0.3932(3) 0.4288(4) 0.6383(4) 0.0318(14) Uani 1 1 d . . . . .
N3 N 0.3638(4) 0.2627(4) 0.6485(4) 0.0417(15) Uani 1 1 d . . . . .
C1 C 0.5078(6) 0.1670(4) 0.5320(4) 0.0379(13) Uani 1 1 d . . . . .
C2 C 0.5573(7) 0.1470(5) 0.4516(5) 0.0563(17) Uani 1 1 d . . . . .
H2 H 0.613677 0.171283 0.442294 0.068 Uiso 1 1 calc R U . . .
C3 C 0.5186(10) 0.0872(6) 0.3827(6) 0.080(2) Uani 1 1 d . . . . .
H3 H 0.552100 0.069828 0.329706 0.096 Uiso 1 1 calc R U . . .
C4 C 0.4363(10) 0.0559(6) 0.3927(6) 0.078(2) Uani 1 1 d . . . . .
H4 H 0.412145 0.019514 0.345228 0.094 Uiso 1 1 calc R U . . .
C5 C 0.3869(7) 0.0765(5) 0.4718(6) 0.064(2) Uani 1 1 d . . . . .
H5 H 0.329789 0.053463 0.479133 0.077 Uiso 1 1 calc R U . . .
C6 C 0.4232(5) 0.1332(4) 0.5421(5) 0.0418(15) Uani 1 1 d . . . . .
C7A C 0.2899(11) 0.3216(12) 0.685(2) 0.042(6) Uani 0.55(5) 1 d . . P A 2
H7A H 0.232861 0.296564 0.666538 0.050 Uiso 0.55(5) 1 calc R U P A 2
H7B H 0.292096 0.323974 0.754634 0.050 Uiso 0.55(5) 1 calc R U P A 2
C7B C 0.2810(15) 0.3043(19) 0.625(4) 0.066(9) Uani 0.45(5) 1 d . . P A 1
H7C H 0.232782 0.280065 0.663300 0.079 Uiso 0.45(5) 1 calc R U P A 1
H7D H 0.266915 0.296381 0.557433 0.079 Uiso 0.45(5) 1 calc R U P A 1
C8 C 0.2972(6) 0.4053(5) 0.6491(6) 0.054(2) Uani 1 1 d . . . . .
H8A H 0.268436 0.447264 0.692051 0.065 Uiso 0.55(5) 1 calc R U P A 2
H8B H 0.267737 0.408552 0.587153 0.065 Uiso 0.55(5) 1 calc R U P A 2
H8C H 0.261726 0.442075 0.606417 0.065 Uiso 0.45(5) 1 calc R U P A 1
H8D H 0.278301 0.417178 0.714485 0.065 Uiso 0.45(5) 1 calc R U P A 1
C9 C 0.4164(6) 0.5103(5) 0.6332(5) 0.0381(19) Uani 1 1 d . . . . .
H9 H 0.371130 0.552550 0.634168 0.046 Uiso 1 1 calc R U . . .
C10 C 0.5060(5) 0.5429(4) 0.6263(5) 0.0346(18) Uani 1 1 d . . . . .
C11 C 0.5213(7) 0.6350(5) 0.6282(5) 0.056(2) Uani 1 1 d . . . . .
H11 H 0.472596 0.673174 0.630078 0.067 Uiso 1 1 calc R U . . .
C12 C 0.6036(8) 0.6703(6) 0.6274(6) 0.067(3) Uani 1 1 d . . . . .
H12 H 0.611309 0.731740 0.627316 0.080 Uiso 1 1 calc R U . . .
C13 C 0.6748(7) 0.6156(7) 0.6266(6) 0.063(3) Uani 1 1 d . . . . .
H13 H 0.732039 0.639156 0.629946 0.076 Uiso 1 1 calc R U . . .
C14 C 0.6625(6) 0.5217(6) 0.6208(5) 0.050(2) Uani 1 1 d . . . . .
H14 H 0.711993 0.484501 0.617506 0.060 Uiso 1 1 calc R U . . .
C15 C 0.5777(6) 0.4848(5) 0.6200(4) 0.0352(19) Uani 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
Zn1 O2 1.837(5) . ?
Zn1 N2 1.859(5) . ?
Zn1 N3 1.882(6) . ?
Zn1 N1 1.985(6) . ?
S1 O3 1.445(6) . ?
S1 O4 1.446(5) . ?
S1 N3 1.556(6) . ?
S1 C6 1.779(8) . ?
O1 N1 1.423(7) . ?
O1 H1 0.8200 . ?
O2 C15 1.325(8) . ?
N1 C1 1.465(8) . ?
N1 H1N 0.9800 . ?
N2 C9 1.275(9) . ?
N2 C8 1.491(10) . ?
N3 C7B 1.43(2) . ?
N3 C7A 1.508(19) . ?
C1 C6 1.375(11) . ?
C1 C2 1.376(11) . ?
C2 C3 1.437(13) . ?
C2 H2 0.9300 . ?
C3 C4 1.330(17) . ?
C3 H3 0.9300 . ?
C4 C5 1.363(15) . ?
C4 H4 0.9300 . ?
C5 C6 1.406(10) . ?
C5 H5 0.9300 . ?
C7A C8 1.356(17) . ?
C7A H7A 0.9700 . ?
C7A H7B 0.9700 . ?
C7B C8 1.57(3) . ?
C7B H7C 0.9700 . ?
C7B H7D 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 H8C 0.9700 . ?
C8 H8D 0.9700 . ?
C9 C10 1.435(11) . ?
C9 H9 0.9300 . ?
C10 C15 1.388(11) . ?
C10 C11 1.402(10) . ?
C11 C12 1.344(14) . ?
C11 H11 0.9300 . ?
C12 C13 1.349(15) . ?
C12 H12 0.9300 . ?
C13 C14 1.424(12) . ?
C13 H13 0.9300 . ?
C14 C15 1.388(12) . ?
C14 H14 0.9300 . ?

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
O2 Zn1 N2 94.3(2) . . ?
O2 Zn1 N3 177.6(2) . . ?
N2 Zn1 N3 85.3(3) . . ?
O2 Zn1 N1 87.1(2) . . ?
N2 Zn1 N1 175.4(2) . . ?
N3 Zn1 N1 93.3(2) . . ?
O3 S1 O4 116.2(3) . . ?
O3 S1 N3 111.4(4) . . ?
O4 S1 N3 111.4(3) . . ?
O3 S1 C6 109.2(4) . . ?
O4 S1 C6 105.1(3) . . ?
N3 S1 C6 102.4(3) . . ?
N1 O1 H1 109.5 . . ?
C15 O2 Zn1 127.8(5) . . ?
O1 N1 C1 109.6(5) . . ?
O1 N1 Zn1 112.6(4) . . ?
C1 N1 Zn1 111.4(4) . . ?
O1 N1 H1N 107.7 . . ?
C1 N1 H1N 107.7 . . ?
Zn1 N1 H1N 107.7 . . ?
C9 N2 C8 119.8(6) . . ?
C9 N2 Zn1 126.4(5) . . ?
C8 N2 Zn1 113.7(5) . . ?
C7B N3 S1 112.2(13) . . ?
C7A N3 S1 123.7(8) . . ?
C7B N3 Zn1 116.9(11) . . ?
C7A N3 Zn1 110.1(8) . . ?
S1 N3 Zn1 125.5(4) . . ?
C6 C1 C2 120.1(7) . . ?
C6 C1 N1 118.5(6) . . ?
C2 C1 N1 121.4(7) . . ?
C1 C2 C3 117.4(10) . . ?
C1 C2 H2 121.3 . . ?
C3 C2 H2 121.3 . . ?
C4 C3 C2 121.8(9) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C3 C4 C5 120.6(9) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C6 119.3(10) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C1 C6 C5 120.7(8) . . ?
C1 C6 S1 120.6(5) . . ?
C5 C6 S1 118.7(7) . . ?
C8 C7A N3 111.1(12) . . ?
C8 C7A H7A 109.4 . . ?
N3 C7A H7A 109.4 . . ?
C8 C7A H7B 109.4 . . ?
N3 C7A H7B 109.4 . . ?
H7A C7A H7B 108.0 . . ?
N3 C7B C8 104(2) . . ?
N3 C7B H7C 111.0 . . ?
C8 C7B H7C 111.0 . . ?
N3 C7B H7D 111.0 . . ?
C8 C7B H7D 111.0 . . ?
H7C C7B H7D 109.0 . . ?
C7A C8 N2 109.5(9) . . ?
N2 C8 C7B 110.8(11) . . ?
C7A C8 H8A 109.8 . . ?
N2 C8 H8A 109.8 . . ?
C7A C8 H8B 109.8 . . ?
N2 C8 H8B 109.8 . . ?
H8A C8 H8B 108.2 . . ?
N2 C8 H8C 109.5 . . ?
C7B C8 H8C 109.5 . . ?
N2 C8 H8D 109.5 . . ?
C7B C8 H8D 109.5 . . ?
H8C C8 H8D 108.1 . . ?
N2 C9 C10 126.0(7) . . ?
N2 C9 H9 117.0 . . ?
C10 C9 H9 117.0 . . ?
C15 C10 C11 119.6(8) . . ?
C15 C10 C9 121.1(6) . . ?
C11 C10 C9 119.3(7) . . ?
C12 C11 C10 122.6(9) . . ?
C12 C11 H11 118.7 . . ?
C10 C11 H11 118.7 . . ?
C11 C12 C13 119.2(9) . . ?
C11 C12 H12 120.4 . . ?
C13 C12 H12 120.4 . . ?
C12 C13 C14 120.0(10) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C15 C14 C13 120.9(9) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
O2 C15 C10 123.8(7) . . ?
O2 C15 C14 118.7(8) . . ?
C10 C15 C14 117.4(7) . . ?

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
_geom_hbond_publ_flag
O1 H1 O2 0.82 1.84 2.497(7) 136.0 . yes
N1 H1N O4 0.98 2.45 3.069(7) 120.5 . yes
N1 H1N O4 0.98 1.98 2.906(7) 155.7 4_656 yes

_refine_diff_density_max         0.309
_refine_diff_density_min         -0.801
_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_Hardeep6b_0m
_database_code_depnum_ccdc_archive 'CCDC 2088570'
loop_
_audit_author_name
_audit_author_address
'Xavier Ottenwaelder' 'Concordia University'
_audit_update_record             
;
2021-06-07 deposited with the CCDC.	2021-08-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
'C23 H31 N3 O4 S Zn, 0.375 (C4 H10 O), 0.125 (C H2 Cl2)'
_chemical_formula_sum            'C24.62 H35 Cl0.25 N3 O4.38 S Zn'
_chemical_formula_weight         549.35

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'
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'
Zn Zn 0.2839 1.4301 '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'

_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                   12.0902(17)
_cell_length_b                   14.849(2)
_cell_length_c                   16.669(2)
_cell_angle_alpha                111.874(2)
_cell_angle_beta                 106.757(2)
_cell_angle_gamma                94.825(2)
_cell_volume                     2596.8(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    4045
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      22.21

_exptl_crystal_description       rhomb
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_F_000             1156
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.284
_exptl_crystal_size_mid          0.095
_exptl_crystal_size_min          0.074
_exptl_absorpt_coefficient_mu    1.089
_shelx_estimated_absorpt_T_min   0.747
_shelx_estimated_absorpt_T_max   0.924
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.610806
_exptl_absorpt_correction_T_max  0.745550
_exptl_absorpt_process_details   'TWINABS, Bruker AXS 2012/1'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11667
_diffrn_reflns_av_unetI/netI     0.1344
_diffrn_reflns_av_R_equivalents  0.1056
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.403
_diffrn_reflns_theta_max         27.475
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             11667
_reflns_number_gt                7302
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0609P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         11667
_refine_ls_number_parameters     680
_refine_ls_number_restraints     79
_refine_ls_R_factor_all          0.1229
_refine_ls_R_factor_gt           0.0691
_refine_ls_wR_factor_ref         0.1659
_refine_ls_wR_factor_gt          0.1480
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.040
_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
Zn1 Zn 0.52529(4) 0.64186(4) 0.78501(3) 0.01309(14) Uani 1 1 d . . . . .
Zn2 Zn 0.34706(5) 0.44469(4) 0.71395(3) 0.01439(14) Uani 1 1 d . . . . .
S1 S 0.34576(10) 0.60199(8) 0.89562(7) 0.0135(2) Uani 1 1 d . . . . .
S2 S 0.32584(10) 0.59305(8) 0.60212(8) 0.0160(2) Uani 1 1 d . . . . .
O1 O 0.4892(3) 0.8450(2) 0.8365(2) 0.0283(8) Uani 1 1 d . . . . .
H1O H 0.548645 0.837563 0.820297 0.042 Uiso 1 1 calc R U . . .
O2 O 0.0887(3) 0.4033(3) 0.6623(3) 0.0378(10) Uani 1 1 d . . . . .
H2O H 0.115862 0.357048 0.672831 0.057 Uiso 1 1 calc R U . . .
O3 O 0.6308(3) 0.7367(2) 0.7662(2) 0.0183(7) Uani 1 1 d . . . . .
O4 O 0.3115(3) 0.5522(2) 0.9466(2) 0.0187(7) Uani 1 1 d . . . . .
O5 O 0.2521(3) 0.6167(2) 0.8273(2) 0.0170(7) Uani 1 1 d . . . . .
O6 O 0.2710(3) 0.3316(2) 0.7303(2) 0.0241(8) Uani 1 1 d . . . . .
O7 O 0.2806(3) 0.6557(2) 0.6695(2) 0.0174(7) Uani 1 1 d . . . . .
O8 O 0.3728(3) 0.6349(2) 0.5507(2) 0.0200(7) Uani 1 1 d . . . . .
N1 N 0.4510(3) 0.7618(3) 0.8520(2) 0.0143(8) Uani 1 1 d . . . . .
H1A H 0.363356 0.740618 0.820136 0.017 Uiso 1 1 calc R U . . .
N2 N 0.1744(3) 0.4600(3) 0.6466(2) 0.0168(8) Uani 1 1 d . . . . .
H2A H 0.171689 0.531295 0.678496 0.020 Uiso 1 1 calc R U . . .
N3 N 0.6622(3) 0.6034(3) 0.8547(3) 0.0174(8) Uani 1 1 d . . . . .
N4 N 0.4324(3) 0.5498(3) 0.8449(2) 0.0134(8) Uani 1 1 d . . . . .
N5 N 0.4463(3) 0.3612(3) 0.6532(2) 0.0166(8) Uani 1 1 d . . . . .
N6 N 0.4200(3) 0.5447(2) 0.6545(2) 0.0124(8) Uani 1 1 d . . . . .
C1 C 0.4726(4) 0.7907(3) 0.9489(3) 0.0143(9) Uani 1 1 d . . . . .
C2 C 0.5341(4) 0.8850(3) 1.0141(3) 0.0184(10) Uani 1 1 d . . . . .
H2 H 0.563232 0.932260 0.995240 0.022 Uiso 1 1 calc R U . . .
C3 C 0.5533(4) 0.9106(4) 1.1061(3) 0.0248(11) Uani 1 1 d . . . . .
H3 H 0.595590 0.975451 1.150161 0.030 Uiso 1 1 calc R U . . .
C4 C 0.5112(4) 0.8420(4) 1.1352(3) 0.0224(11) Uani 1 1 d . . . . .
H4 H 0.524646 0.859839 1.198723 0.027 Uiso 1 1 calc R U . . .
C5 C 0.4496(4) 0.7475(3) 1.0701(3) 0.0187(10) Uani 1 1 d . . . . .
H5 H 0.421246 0.700077 1.089102 0.022 Uiso 1 1 calc R U . . .
C6 C 0.4294(4) 0.7219(3) 0.9775(3) 0.0137(9) Uani 1 1 d . . . . .
C7 C 0.5278(4) 0.5257(3) 0.9078(3) 0.0152(10) Uani 1 1 d . . . . .
H7A H 0.498142 0.461245 0.907429 0.018 Uiso 1 1 calc R U . . .
H7AB H 0.549987 0.577369 0.971460 0.018 Uiso 1 1 calc R U . . .
C8 C 0.6365(4) 0.5199(3) 0.8787(3) 0.0179(10) Uani 1 1 d . . . . .
H8A H 0.705361 0.522362 0.929720 0.021 Uiso 1 1 calc R U . . .
H8AB H 0.622180 0.456160 0.824892 0.021 Uiso 1 1 calc R U . . .
C9 C 0.7710(4) 0.6502(3) 0.8825(3) 0.0144(9) Uani 1 1 d . . . . .
H9 H 0.827783 0.631863 0.923014 0.017 Uiso 1 1 calc R U . . .
C10 C 0.8163(4) 0.7263(3) 0.8598(3) 0.0166(10) Uani 1 1 d . . . . .
C11 C 0.9399(4) 0.7639(3) 0.9011(3) 0.0162(10) Uani 1 1 d . . . . .
H11 H 0.984144 0.740949 0.943868 0.019 Uiso 1 1 calc R U . . .
C12 C 0.9988(4) 0.8324(3) 0.8818(3) 0.0157(10) Uani 1 1 d . . . . .
C13 C 0.9288(4) 0.8598(3) 0.8147(3) 0.0152(10) Uani 1 1 d . . . . .
H13 H 0.967839 0.904010 0.797557 0.018 Uiso 1 1 calc R U . . .
C14 C 0.8070(4) 0.8270(3) 0.7717(3) 0.0148(9) Uani 1 1 d . . . . .
C15 C 0.7476(4) 0.7618(3) 0.7982(3) 0.0150(9) Uani 1 1 d . . . . .
C16 C 1.1315(4) 0.8788(3) 0.9291(3) 0.0179(10) Uani 1 1 d . . . . .
C17 C 1.1908(4) 0.8385(4) 0.9985(3) 0.0243(11) Uani 1 1 d . . . . .
H17A H 1.274073 0.873128 1.030378 0.036 Uiso 1 1 calc R U . . .
H17B H 1.185931 0.767181 0.966307 0.036 Uiso 1 1 calc R U . . .
H17C H 1.150641 0.849200 1.043617 0.036 Uiso 1 1 calc R U . . .
C18 C 1.1922(4) 0.8571(3) 0.8558(3) 0.0224(11) Uani 1 1 d . . . . .
H18A H 1.276161 0.889895 0.885918 0.034 Uiso 1 1 calc R U . . .
H18B H 1.154289 0.882340 0.810575 0.034 Uiso 1 1 calc R U . . .
H18C H 1.184602 0.785198 0.824621 0.034 Uiso 1 1 calc R U . . .
C19 C 1.1490(4) 0.9918(3) 0.9811(3) 0.0226(11) Uani 1 1 d . . . . .
H19A H 1.233648 1.022274 1.007726 0.034 Uiso 1 1 calc R U . . .
H19B H 1.115568 1.005867 1.030385 0.034 Uiso 1 1 calc R U . . .
H19C H 1.108841 1.019166 0.938248 0.034 Uiso 1 1 calc R U . . .
C20 C 0.7393(4) 0.8595(3) 0.6971(3) 0.0207(11) Uani 1 1 d . . . . .
C21 C 0.6708(5) 0.7679(4) 0.6080(3) 0.0290(12) Uani 1 1 d . . . . .
H21A H 0.622099 0.788593 0.562649 0.044 Uiso 1 1 calc R U . . .
H21B H 0.619858 0.723960 0.620702 0.044 Uiso 1 1 calc R U . . .
H21C H 0.726719 0.732278 0.583504 0.044 Uiso 1 1 calc R U . . .
C22 C 0.6542(5) 0.9225(4) 0.7288(4) 0.0331(13) Uani 1 1 d . . . . .
H22A H 0.628703 0.957107 0.689067 0.050 Uiso 1 1 calc R U . . .
H22B H 0.694137 0.971328 0.792583 0.050 Uiso 1 1 calc R U . . .
H22C H 0.585084 0.879557 0.725104 0.050 Uiso 1 1 calc R U . . .
C23 C 0.8215(5) 0.9217(4) 0.6735(4) 0.0381(15) Uani 1 1 d . . . . .
H23A H 0.774787 0.937027 0.623386 0.057 Uiso 1 1 calc R U . . .
H23B H 0.879104 0.884245 0.654169 0.057 Uiso 1 1 calc R U . . .
H23C H 0.863172 0.983685 0.727939 0.057 Uiso 1 1 calc R U . . .
C24 C 0.1402(4) 0.4377(3) 0.5493(3) 0.0188(10) Uani 1 1 d . . . . .
C25 C 0.0448(4) 0.3614(4) 0.4844(3) 0.0257(12) Uani 1 1 d . . . . .
H25 H -0.001363 0.323608 0.503108 0.031 Uiso 1 1 calc R U . . .
C26 C 0.0179(4) 0.3410(4) 0.3917(3) 0.0296(12) Uani 1 1 d . . . . .
H26 H -0.046604 0.288318 0.347155 0.036 Uiso 1 1 calc R U . . .
C27 C 0.0826(5) 0.3955(4) 0.3628(3) 0.0287(12) Uani 1 1 d . . . . .
H27 H 0.061908 0.380629 0.299083 0.034 Uiso 1 1 calc R U . . .
C28 C 0.1777(4) 0.4719(4) 0.4266(3) 0.0248(11) Uani 1 1 d . . . . .
H28 H 0.222844 0.509392 0.406994 0.030 Uiso 1 1 calc R U . . .
C29 C 0.2066(4) 0.4934(3) 0.5205(3) 0.0177(10) Uani 1 1 d . . . . .
C30 C 0.4808(4) 0.4844(3) 0.5935(3) 0.0183(10) Uani 1 1 d . . . . .
H30A H 0.543975 0.529023 0.590885 0.022 Uiso 1 1 calc R U . . .
H30B H 0.423300 0.446810 0.530290 0.022 Uiso 1 1 calc R U . . .
C31 C 0.5339(4) 0.4129(3) 0.6302(3) 0.0178(10) Uani 1 1 d . . . . .
H31A H 0.558568 0.363724 0.583240 0.021 Uiso 1 1 calc R U . . .
H31B H 0.604847 0.449776 0.685881 0.021 Uiso 1 1 calc R U . . .
C32 C 0.4319(4) 0.2667(3) 0.6287(3) 0.0208(11) Uani 1 1 d . . . . .
H32 H 0.479511 0.234764 0.595161 0.025 Uiso 1 1 calc R U . . .
C33 C 0.3539(4) 0.2035(3) 0.6453(3) 0.0183(10) Uani 1 1 d . . . . .
C34 C 0.3534(4) 0.1009(3) 0.6052(3) 0.0216(11) Uani 1 1 d . . . . .
H34 H 0.402397 0.078970 0.569497 0.026 Uiso 1 1 calc R U . . .
C35 C 0.2839(4) 0.0329(3) 0.6167(3) 0.0231(11) Uani 1 1 d . . . . .
C36 C 0.2214(4) 0.0691(3) 0.6760(3) 0.0223(11) Uani 1 1 d . . . . .
H36 H 0.176182 0.022232 0.686854 0.027 Uiso 1 1 calc R U . . .
C37 C 0.2203(4) 0.1676(3) 0.7198(3) 0.0197(10) Uani 1 1 d . . . . .
C38 C 0.2824(4) 0.2381(3) 0.6993(3) 0.0182(10) Uani 1 1 d . . . . .
C39 C 0.2736(5) -0.0803(4) 0.5685(4) 0.0351(14) Uani 1 1 d . . . . .
C40 C 0.1457(6) -0.1273(4) 0.5048(5) 0.062(2) Uani 1 1 d . . . . .
H40A H 0.136549 -0.199425 0.474037 0.093 Uiso 1 1 calc R U . . .
H40B H 0.125165 -0.100084 0.458473 0.093 Uiso 1 1 calc R U . . .
H40C H 0.093200 -0.112611 0.540992 0.093 Uiso 1 1 calc R U . . .
C41 C 0.3584(6) -0.1055(4) 0.5141(4) 0.0513(18) Uani 1 1 d . . . . .
H41A H 0.353079 -0.177452 0.488419 0.077 Uiso 1 1 calc R U . . .
H41B H 0.439615 -0.071359 0.555320 0.077 Uiso 1 1 calc R U . . .
H41C H 0.336664 -0.083820 0.463956 0.077 Uiso 1 1 calc R U . . .
C42 C 0.3046(6) -0.1242(4) 0.6411(4) 0.0471(17) Uani 1 1 d . . . . .
H42A H 0.299432 -0.195785 0.610166 0.071 Uiso 1 1 calc R U . . .
H42B H 0.248791 -0.112995 0.674574 0.071 Uiso 1 1 calc R U . . .
H42C H 0.385195 -0.091777 0.684619 0.071 Uiso 1 1 calc R U . . .
C43 C 0.1535(4) 0.2018(3) 0.7884(3) 0.0245(11) Uani 1 1 d . . . . .
C44 C 0.1166(5) 0.1178(4) 0.8149(4) 0.0430(15) Uani 1 1 d . . . . .
H44A H 0.084227 0.144024 0.864464 0.065 Uiso 1 1 calc R U . . .
H44B H 0.185733 0.091609 0.835846 0.065 Uiso 1 1 calc R U . . .
H44C H 0.056237 0.064386 0.761069 0.065 Uiso 1 1 calc R U . . .
C45 C 0.2330(5) 0.2860(4) 0.8795(3) 0.0304(13) Uani 1 1 d . . . . .
H45A H 0.188724 0.305538 0.921875 0.046 Uiso 1 1 calc R U . . .
H45B H 0.259029 0.343168 0.868318 0.046 Uiso 1 1 calc R U . . .
H45C H 0.302175 0.263458 0.906793 0.046 Uiso 1 1 calc R U . . .
C46 C 0.0399(5) 0.2326(5) 0.7475(4) 0.0476(16) Uani 1 1 d . . . . .
H46A H -0.000155 0.253530 0.792716 0.071 Uiso 1 1 calc R U . . .
H46B H -0.012654 0.176089 0.691717 0.071 Uiso 1 1 calc R U . . .
H46C H 0.059954 0.287858 0.731945 0.071 Uiso 1 1 calc R U . . .
O9 O -0.1550(5) 0.3697(4) 0.8109(4) 0.0511(12) Uani 0.75 1 d D U P . .
C47A C 0.0065(7) 0.5086(6) 0.8501(5) 0.073(2) Uani 0.5 1 d D U P A 1
H47A H 0.032731 0.553202 0.825054 0.110 Uiso 0.5 1 calc R U P A 1
H47B H -0.005469 0.547933 0.907752 0.110 Uiso 0.5 1 calc R U P A 1
H47C H 0.066687 0.470522 0.862107 0.110 Uiso 0.5 1 calc R U P A 1
C48A C -0.111(2) 0.437(2) 0.780(2) 0.0510(14) Uani 0.5 1 d D U P A 1
H48A H -0.170400 0.476012 0.767315 0.061 Uiso 0.5 1 calc R U P A 1
H48B H -0.098290 0.398650 0.721700 0.061 Uiso 0.5 1 calc R U P A 1
C49A C -0.2382(11) 0.2919(9) 0.7389(9) 0.0515(13) Uani 0.5 1 d D U P A 1
H49A H -0.203952 0.258234 0.691357 0.062 Uiso 0.5 1 calc R U P A 1
H49B H -0.305922 0.316528 0.710772 0.062 Uiso 0.5 1 calc R U P A 1
C50A C -0.2802(8) 0.2192(6) 0.7737(6) 0.0516(13) Uani 0.5 1 d D U P A 1
H50A H -0.254239 0.157190 0.748457 0.077 Uiso 0.5 1 calc R U P A 1
H50B H -0.366723 0.205528 0.754080 0.077 Uiso 0.5 1 calc R U P A 1
H50C H -0.246656 0.248050 0.841172 0.077 Uiso 0.5 1 calc R U P A 1
C47B C 0.0065(7) 0.5086(6) 0.8501(5) 0.073(2) Uani 0.25 1 d D U P A 2
H47D H 0.067403 0.559603 0.905451 0.110 Uiso 0.25 1 calc R U P A 2
H47E H 0.044204 0.467033 0.809605 0.110 Uiso 0.25 1 calc R U P A 2
H47F H -0.045348 0.540719 0.817566 0.110 Uiso 0.25 1 calc R U P A 2
C48B C -0.065(2) 0.4458(17) 0.8770(15) 0.0510(14) Uani 0.25 1 d D U P A 2
H48C H -0.009286 0.417199 0.912230 0.061 Uiso 0.25 1 calc R U P A 2
H48D H -0.098311 0.490452 0.920143 0.061 Uiso 0.25 1 calc R U P A 2
C49B C -0.186(2) 0.3101(15) 0.8560(14) 0.0511(13) Uani 0.25 1 d D U P A 2
H49C H -0.219963 0.346869 0.902692 0.061 Uiso 0.25 1 calc R U P A 2
H49D H -0.116172 0.288686 0.885899 0.061 Uiso 0.25 1 calc R U P A 2
C50B C -0.2802(8) 0.2192(6) 0.7737(6) 0.0516(13) Uani 0.25 1 d D U P A 2
H50D H -0.334451 0.242946 0.733754 0.077 Uiso 0.25 1 calc R U P A 2
H50E H -0.324882 0.184069 0.797851 0.077 Uiso 0.25 1 calc R U P A 2
H50F H -0.240113 0.173942 0.738265 0.077 Uiso 0.25 1 calc R U P A 2
C47C C 0.0065(7) 0.5086(6) 0.8501(5) 0.073(2) Uani 0.25 1 d . U P A 3
H47G H 0.026514 0.569926 0.841925 0.088 Uiso 0.25 1 calc R U P A 3
H47H H 0.063612 0.467746 0.833334 0.088 Uiso 0.25 1 calc R U P A 3
Cl1 Cl 0.0387(6) 0.5454(6) 0.9690(5) 0.064(2) Uani 0.25 1 d . . P A 3
Cl2 Cl -0.1183(12) 0.4503(10) 0.7746(10) 0.056(2) Uani 0.25 1 d . U P A 3


_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
Zn1 N3 1.991(4) . ?
Zn1 O3 1.991(3) . ?
Zn1 N6 2.047(4) . ?
Zn1 N1 2.143(4) . ?
Zn1 N4 2.351(4) . ?
Zn1 Zn2 3.0824(8) . ?
Zn2 O6 1.992(3) . ?
Zn2 N5 2.004(4) . ?
Zn2 N4 2.039(4) . ?
Zn2 N2 2.142(4) . ?
Zn2 N6 2.312(3) . ?
S1 O4 1.435(3) . ?
S1 O5 1.452(3) . ?
S1 N4 1.604(4) . ?
S1 C6 1.774(4) . ?
S2 O8 1.436(3) . ?
S2 O7 1.445(3) . ?
S2 N6 1.615(4) . ?
S2 C29 1.769(5) . ?
O1 N1 1.420(4) . ?
O1 H1O 0.8400 . ?
O2 N2 1.423(5) . ?
O2 H2O 0.8400 . ?
O3 C15 1.322(5) . ?
O6 C38 1.324(5) . ?
N1 C1 1.442(5) . ?
N1 H1A 1.0000 . ?
N2 C24 1.449(6) . ?
N2 H2A 1.0000 . ?
N3 C9 1.298(5) . ?
N3 C8 1.473(5) . ?
N4 C7 1.487(5) . ?
N5 C32 1.287(6) . ?
N5 C31 1.476(5) . ?
N6 C30 1.496(5) . ?
C1 C2 1.386(6) . ?
C1 C6 1.400(6) . ?
C2 C3 1.376(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.399(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.388(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.384(6) . ?
C5 H5 0.9500 . ?
C7 C8 1.526(6) . ?
C7 H7A 0.9900 . ?
C7 H7AB 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8AB 0.9900 . ?
C9 C10 1.433(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.414(6) . ?
C10 C15 1.417(6) . ?
C11 C12 1.378(6) . ?
C11 H11 0.9500 . ?
C12 C13 1.408(6) . ?
C12 C16 1.533(6) . ?
C13 C14 1.389(6) . ?
C13 H13 0.9500 . ?
C14 C15 1.425(6) . ?
C14 C20 1.542(6) . ?
C16 C17 1.525(6) . ?
C16 C19 1.536(6) . ?
C16 C18 1.548(6) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C22 1.522(7) . ?
C20 C23 1.528(6) . ?
C20 C21 1.529(6) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 C25 1.390(6) . ?
C24 C29 1.402(6) . ?
C25 C26 1.389(7) . ?
C25 H25 0.9500 . ?
C26 C27 1.378(7) . ?
C26 H26 0.9500 . ?
C27 C28 1.384(7) . ?
C27 H27 0.9500 . ?
C28 C29 1.403(6) . ?
C28 H28 0.9500 . ?
C30 C31 1.511(6) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 C33 1.429(6) . ?
C32 H32 0.9500 . ?
C33 C38 1.414(6) . ?
C33 C34 1.417(6) . ?
C34 C35 1.362(6) . ?
C34 H34 0.9500 . ?
C35 C36 1.393(7) . ?
C35 C39 1.545(7) . ?
C36 C37 1.374(6) . ?
C36 H36 0.9500 . ?
C37 C38 1.434(6) . ?
C37 C43 1.544(7) . ?
C39 C40 1.525(8) . ?
C39 C41 1.536(8) . ?
C39 C42 1.550(7) . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?
C43 C45 1.529(7) . ?
C43 C46 1.536(7) . ?
C43 C44 1.543(7) . ?
C44 H44A 0.9800 . ?
C44 H44B 0.9800 . ?
C44 H44C 0.9800 . ?
C45 H45A 0.9800 . ?
C45 H45B 0.9800 . ?
C45 H45C 0.9800 . ?
C46 H46A 0.9800 . ?
C46 H46B 0.9800 . ?
C46 H46C 0.9800 . ?
O9 C48B 1.36(2) . ?
O9 C49A 1.365(13) . ?
O9 C48A 1.41(2) . ?
O9 C49B 1.445(17) . ?
O9 Cl2 1.613(15) . ?
C47A C48A 1.54(2) . ?
C47A H47A 0.9800 . ?
C47A H47B 0.9800 . ?
C47A H47C 0.9800 . ?
C48A H48A 0.9900 . ?
C48A H48B 0.9900 . ?
C49A C50A 1.518(13) . ?
C49A H49A 0.9900 . ?
C49A H49B 0.9900 . ?
C50A H50A 0.9800 . ?
C50A H50B 0.9800 . ?
C50A H50C 0.9800 . ?
C47B C48B 1.49(2) . ?
C47B H47D 0.9800 . ?
C47B H47E 0.9800 . ?
C47B H47F 0.9800 . ?
C48B H48C 0.9900 . ?
C48B H48D 0.9900 . ?
C49B C50B 1.570(18) . ?
C49B H49C 0.9900 . ?
C49B H49D 0.9900 . ?
C50B H50D 0.9800 . ?
C50B H50E 0.9800 . ?
C50B H50F 0.9800 . ?
C47C Cl2 1.576(16) . ?
C47C Cl1 1.757(10) . ?
C47C H47G 0.9900 . ?
C47C H47H 0.9900 . ?
Cl1 Cl1 2.269(15) 2_567 ?

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
N3 Zn1 O3 92.12(14) . . ?
N3 Zn1 N6 120.09(15) . . ?
O3 Zn1 N6 104.33(13) . . ?
N3 Zn1 N1 122.05(15) . . ?
O3 Zn1 N1 89.23(13) . . ?
N6 Zn1 N1 115.48(14) . . ?
N3 Zn1 N4 78.65(14) . . ?
O3 Zn1 N4 165.93(12) . . ?
N6 Zn1 N4 89.55(13) . . ?
N1 Zn1 N4 86.80(12) . . ?
N3 Zn1 Zn2 96.21(11) . . ?
O3 Zn1 Zn2 151.80(9) . . ?
N6 Zn1 Zn2 48.60(9) . . ?
N1 Zn1 Zn2 108.63(10) . . ?
N4 Zn1 Zn2 41.40(9) . . ?
O6 Zn2 N5 91.34(14) . . ?
O6 Zn2 N4 104.34(13) . . ?
N5 Zn2 N4 116.36(15) . . ?
O6 Zn2 N2 88.75(14) . . ?
N5 Zn2 N2 126.34(15) . . ?
N4 Zn2 N2 115.47(14) . . ?
O6 Zn2 N6 164.56(13) . . ?
N5 Zn2 N6 79.21(14) . . ?
N4 Zn2 N6 90.85(13) . . ?
N2 Zn2 N6 87.14(13) . . ?
O6 Zn2 Zn1 152.72(10) . . ?
N5 Zn2 Zn1 94.12(11) . . ?
N4 Zn2 Zn1 49.69(10) . . ?
N2 Zn2 Zn1 109.03(10) . . ?
N6 Zn2 Zn1 41.62(9) . . ?
O4 S1 O5 117.57(19) . . ?
O4 S1 N4 112.68(18) . . ?
O5 S1 N4 106.90(18) . . ?
O4 S1 C6 106.52(19) . . ?
O5 S1 C6 106.60(19) . . ?
N4 S1 C6 105.8(2) . . ?
O8 S2 O7 118.59(19) . . ?
O8 S2 N6 111.95(19) . . ?
O7 S2 N6 106.59(18) . . ?
O8 S2 C29 106.4(2) . . ?
O7 S2 C29 106.5(2) . . ?
N6 S2 C29 105.9(2) . . ?
N1 O1 H1O 109.5 . . ?
N2 O2 H2O 109.5 . . ?
C15 O3 Zn1 128.8(3) . . ?
C38 O6 Zn2 128.7(3) . . ?
O1 N1 C1 110.2(3) . . ?
O1 N1 Zn1 108.5(2) . . ?
C1 N1 Zn1 117.2(3) . . ?
O1 N1 H1A 106.8 . . ?
C1 N1 H1A 106.8 . . ?
Zn1 N1 H1A 106.8 . . ?
O2 N2 C24 109.9(3) . . ?
O2 N2 Zn2 109.1(3) . . ?
C24 N2 Zn2 117.8(3) . . ?
O2 N2 H2A 106.5 . . ?
C24 N2 H2A 106.5 . . ?
Zn2 N2 H2A 106.5 . . ?
C9 N3 C8 119.1(4) . . ?
C9 N3 Zn1 123.4(3) . . ?
C8 N3 Zn1 117.5(3) . . ?
C7 N4 S1 111.1(3) . . ?
C7 N4 Zn2 118.4(3) . . ?
S1 N4 Zn2 114.0(2) . . ?
C7 N4 Zn1 106.9(2) . . ?
S1 N4 Zn1 115.67(18) . . ?
Zn2 N4 Zn1 88.91(13) . . ?
C32 N5 C31 119.9(4) . . ?
C32 N5 Zn2 124.0(3) . . ?
C31 N5 Zn2 116.0(3) . . ?
C30 N6 S2 111.7(3) . . ?
C30 N6 Zn1 116.7(3) . . ?
S2 N6 Zn1 113.69(19) . . ?
C30 N6 Zn2 106.8(2) . . ?
S2 N6 Zn2 116.41(19) . . ?
Zn1 N6 Zn2 89.78(13) . . ?
C2 C1 C6 119.3(4) . . ?
C2 C1 N1 121.6(4) . . ?
C6 C1 N1 119.1(4) . . ?
C3 C2 C1 120.4(4) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 120.6(4) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 119.1(4) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C6 C5 C4 120.3(4) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C1 120.3(4) . . ?
C5 C6 S1 119.2(3) . . ?
C1 C6 S1 120.5(3) . . ?
N4 C7 C8 111.1(3) . . ?
N4 C7 H7A 109.4 . . ?
C8 C7 H7A 109.4 . . ?
N4 C7 H7AB 109.4 . . ?
C8 C7 H7AB 109.4 . . ?
H7A C7 H7AB 108.0 . . ?
N3 C8 C7 110.0(3) . . ?
N3 C8 H8A 109.7 . . ?
C7 C8 H8A 109.7 . . ?
N3 C8 H8AB 109.7 . . ?
C7 C8 H8AB 109.7 . . ?
H8A C8 H8AB 108.2 . . ?
N3 C9 C10 128.1(4) . . ?
N3 C9 H9 116.0 . . ?
C10 C9 H9 116.0 . . ?
C11 C10 C15 119.8(4) . . ?
C11 C10 C9 115.2(4) . . ?
C15 C10 C9 125.0(4) . . ?
C12 C11 C10 122.7(4) . . ?
C12 C11 H11 118.6 . . ?
C10 C11 H11 118.6 . . ?
C11 C12 C13 115.7(4) . . ?
C11 C12 C16 124.1(4) . . ?
C13 C12 C16 120.2(4) . . ?
C14 C13 C12 125.0(4) . . ?
C14 C13 H13 117.5 . . ?
C12 C13 H13 117.5 . . ?
C13 C14 C15 117.8(4) . . ?
C13 C14 C20 120.8(4) . . ?
C15 C14 C20 121.4(4) . . ?
O3 C15 C10 121.4(4) . . ?
O3 C15 C14 120.0(4) . . ?
C10 C15 C14 118.6(4) . . ?
C17 C16 C12 111.8(4) . . ?
C17 C16 C19 107.9(4) . . ?
C12 C16 C19 109.2(4) . . ?
C17 C16 C18 108.9(4) . . ?
C12 C16 C18 109.7(4) . . ?
C19 C16 C18 109.3(4) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C22 C20 C23 106.9(4) . . ?
C22 C20 C21 109.8(4) . . ?
C23 C20 C21 106.8(4) . . ?
C22 C20 C14 110.9(4) . . ?
C23 C20 C14 112.6(4) . . ?
C21 C20 C14 109.8(4) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C25 C24 C29 119.7(4) . . ?
C25 C24 N2 121.5(4) . . ?
C29 C24 N2 118.9(4) . . ?
C26 C25 C24 119.2(5) . . ?
C26 C25 H25 120.4 . . ?
C24 C25 H25 120.4 . . ?
C27 C26 C25 121.5(5) . . ?
C27 C26 H26 119.2 . . ?
C25 C26 H26 119.2 . . ?
C26 C27 C28 120.0(5) . . ?
C26 C27 H27 120.0 . . ?
C28 C27 H27 120.0 . . ?
C27 C28 C29 119.3(5) . . ?
C27 C28 H28 120.4 . . ?
C29 C28 H28 120.4 . . ?
C24 C29 C28 120.3(4) . . ?
C24 C29 S2 120.5(3) . . ?
C28 C29 S2 119.2(4) . . ?
N6 C30 C31 110.1(3) . . ?
N6 C30 H30A 109.6 . . ?
C31 C30 H30A 109.6 . . ?
N6 C30 H30B 109.6 . . ?
C31 C30 H30B 109.6 . . ?
H30A C30 H30B 108.2 . . ?
N5 C31 C30 109.9(4) . . ?
N5 C31 H31A 109.7 . . ?
C30 C31 H31A 109.7 . . ?
N5 C31 H31B 109.7 . . ?
C30 C31 H31B 109.7 . . ?
H31A C31 H31B 108.2 . . ?
N5 C32 C33 128.6(4) . . ?
N5 C32 H32 115.7 . . ?
C33 C32 H32 115.7 . . ?
C38 C33 C34 120.4(4) . . ?
C38 C33 C32 124.0(4) . . ?
C34 C33 C32 115.5(4) . . ?
C35 C34 C33 121.3(4) . . ?
C35 C34 H34 119.3 . . ?
C33 C34 H34 119.3 . . ?
C34 C35 C36 117.3(4) . . ?
C34 C35 C39 123.0(5) . . ?
C36 C35 C39 119.7(4) . . ?
C37 C36 C35 124.7(5) . . ?
C37 C36 H36 117.6 . . ?
C35 C36 H36 117.6 . . ?
C36 C37 C38 117.9(4) . . ?
C36 C37 C43 121.3(4) . . ?
C38 C37 C43 120.8(4) . . ?
O6 C38 C33 122.4(4) . . ?
O6 C38 C37 119.9(4) . . ?
C33 C38 C37 117.7(4) . . ?
C40 C39 C41 110.6(5) . . ?
C40 C39 C35 107.9(5) . . ?
C41 C39 C35 112.2(4) . . ?
C40 C39 C42 108.8(5) . . ?
C41 C39 C42 107.4(5) . . ?
C35 C39 C42 109.9(4) . . ?
C39 C40 H40A 109.5 . . ?
C39 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C39 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C39 C41 H41A 109.5 . . ?
C39 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
C39 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C39 C42 H42A 109.5 . . ?
C39 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C39 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C45 C43 C46 110.6(4) . . ?
C45 C43 C44 104.7(4) . . ?
C46 C43 C44 106.9(4) . . ?
C45 C43 C37 111.3(4) . . ?
C46 C43 C37 111.8(4) . . ?
C44 C43 C37 111.3(4) . . ?
C43 C44 H44A 109.5 . . ?
C43 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
C43 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
C43 C45 H45A 109.5 . . ?
C43 C45 H45B 109.5 . . ?
H45A C45 H45B 109.5 . . ?
C43 C45 H45C 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 109.5 . . ?
C43 C46 H46A 109.5 . . ?
C43 C46 H46B 109.5 . . ?
H46A C46 H46B 109.5 . . ?
C43 C46 H46C 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
C49A O9 C48A 110.6(12) . . ?
C48B O9 C49B 105.7(13) . . ?
C48A C47A H47A 109.5 . . ?
C48A C47A H47B 109.5 . . ?
H47A C47A H47B 109.5 . . ?
C48A C47A H47C 109.5 . . ?
H47A C47A H47C 109.5 . . ?
H47B C47A H47C 109.5 . . ?
O9 C48A C47A 113.2(16) . . ?
O9 C48A H48A 108.9 . . ?
C47A C48A H48A 108.9 . . ?
O9 C48A H48B 108.9 . . ?
C47A C48A H48B 108.9 . . ?
H48A C48A H48B 107.8 . . ?
O9 C49A C50A 109.2(9) . . ?
O9 C49A H49A 109.8 . . ?
C50A C49A H49A 109.8 . . ?
O9 C49A H49B 109.8 . . ?
C50A C49A H49B 109.8 . . ?
H49A C49A H49B 108.3 . . ?
C49A C50A H50A 109.5 . . ?
C49A C50A H50B 109.5 . . ?
H50A C50A H50B 109.5 . . ?
C49A C50A H50C 109.5 . . ?
H50A C50A H50C 109.5 . . ?
H50B C50A H50C 109.5 . . ?
C48B C47B H47D 109.5 . . ?
C48B C47B H47E 109.5 . . ?
H47D C47B H47E 109.5 . . ?
C48B C47B H47F 109.5 . . ?
H47D C47B H47F 109.5 . . ?
H47E C47B H47F 109.5 . . ?
O9 C48B C47B 119.8(16) . . ?
O9 C48B H48C 107.4 . . ?
C47B C48B H48C 107.4 . . ?
O9 C48B H48D 107.4 . . ?
C47B C48B H48D 107.4 . . ?
H48C C48B H48D 106.9 . . ?
O9 C49B C50B 102.4(12) . . ?
O9 C49B H49C 111.3 . . ?
C50B C49B H49C 111.3 . . ?
O9 C49B H49D 111.3 . . ?
C50B C49B H49D 111.3 . . ?
H49C C49B H49D 109.2 . . ?
C49B C50B H50D 109.5 . . ?
C49B C50B H50E 109.5 . . ?
H50D C50B H50E 109.5 . . ?
C49B C50B H50F 109.5 . . ?
H50D C50B H50F 109.5 . . ?
H50E C50B H50F 109.5 . . ?
Cl2 C47C Cl1 124.3(8) . . ?
Cl2 C47C H47G 106.3 . . ?
Cl1 C47C H47G 106.3 . . ?
Cl2 C47C H47H 106.3 . . ?
Cl1 C47C H47H 106.3 . . ?
H47G C47C H47H 106.4 . . ?
C47C Cl1 Cl1 124.1(7) . 2_567 ?
C47C Cl2 O9 101.2(7) . . ?

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
_geom_hbond_publ_flag
O1 H1O O3 0.84 1.95 2.666(5) 142.5 . yes
O2 H2O O6 0.84 1.98 2.671(5) 138.5 . yes
N1 H1A O5 1.00 2.25 2.914(5) 122.9 . yes
N1 H1A O7 1.00 2.21 2.873(5) 122.6 . yes
N2 H2A O5 1.00 2.18 2.855(5) 123.1 . yes
N2 H2A O7 1.00 2.25 2.915(5) 122.5 . yes

_refine_diff_density_max         0.951
_refine_diff_density_min         -0.655
_refine_diff_density_rms         0.127



####################################################################### 
# 
# 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_cu_Fed5_0ma
_database_code_depnum_ccdc_archive 'CCDC 2089089'
loop_
_audit_author_name
_audit_author_address
'Xavier Ottenwaelder' 'Concordia University'
_audit_update_record             
;
2021-06-09 deposited with the CCDC.	2021-08-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H31 N3 O5 S'
_chemical_formula_sum            'C23 H31 N3 O5 S'
_chemical_formula_weight         461.57

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

_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'
'-x, y, -z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'
'x-1/2, y-1/2, -z-1/2'

_cell_length_a                   19.5284(10)
_cell_length_b                   7.3377(4)
_cell_length_c                   34.2044(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4901.3(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    9889
_cell_measurement_theta_min      2.58
_cell_measurement_theta_max      63.35

_exptl_crystal_description       rod
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_F_000             1968
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.485
_shelx_estimated_absorpt_T_min   0.664
_shelx_estimated_absorpt_T_max   0.866
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6996
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_process_details   'SADABS-2016/2 - Bruker AXS'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            41231
_diffrn_reflns_av_unetI/netI     0.0194
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_theta_min         2.584
_diffrn_reflns_theta_max         68.319
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.976
_reflns_number_total             4385
_reflns_number_gt                3809
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0506P)²+5.8209P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4385
_refine_ls_number_parameters     296
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0460
_refine_ls_wR_factor_ref         0.1246
_refine_ls_wR_factor_gt          0.1212
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_restrained_S_all      1.108
_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
S1 S 0.64842(3) 0.24580(7) 0.22343(2) 0.01651(14) Uani 1 1 d . . . . .
O1 O 0.72027(8) 0.4235(2) 0.15448(5) 0.0295(4) Uani 1 1 d . . . . .
O2 O 0.71274(9) 0.2529(3) 0.10291(5) 0.0353(4) Uani 1 1 d . . . . .
O3 O 0.60568(8) 0.1777(2) 0.25412(4) 0.0242(3) Uani 1 1 d . . . . .
O4 O 0.70792(8) 0.1456(2) 0.21133(4) 0.0248(4) Uani 1 1 d . . . . .
O5 O 0.46217(8) 0.7157(2) 0.17275(4) 0.0252(4) Uani 1 1 d . . . . .
H5 H 0.490273 0.721407 0.191297 0.038 Uiso 1 1 calc R U . . .
N1 N 0.67272(9) 0.4445(3) 0.23606(5) 0.0210(4) Uani 1 1 d . . . . .
H1 H 0.712484 0.484167 0.227441 0.025 Uiso 1 1 calc R U . . .
N2 N 0.57856(9) 0.7391(2) 0.20821(5) 0.0191(4) Uani 1 1 d . . . . .
N3 N 0.68887(10) 0.3187(3) 0.13289(5) 0.0244(4) Uani 1 1 d . . . . .
C1 C 0.56622(13) 0.7539(4) -0.00747(6) 0.0295(5) Uani 1 1 d . . . . .
H1D H 0.534215 0.856794 -0.007615 0.044 Uiso 1 1 calc R U . . .
H1E H 0.540442 0.639329 -0.007452 0.044 Uiso 1 1 calc R U . . .
H1F H 0.595280 0.759439 -0.030795 0.044 Uiso 1 1 calc R U . . .
C2 C 0.61116(12) 0.7636(3) 0.02925(6) 0.0240(5) Uani 1 1 d . . . . .
C3 C 0.56937(12) 0.7556(3) 0.06735(6) 0.0209(5) Uani 1 1 d . . . . .
C4 C 0.60342(11) 0.7625(3) 0.10297(6) 0.0208(5) Uani 1 1 d . . . . .
H4 H 0.651812 0.775776 0.103291 0.025 Uiso 1 1 calc R U . . .
C5 C 0.56795(11) 0.7503(3) 0.13831(6) 0.0188(4) Uani 1 1 d . . . . .
C6 C 0.60675(11) 0.7596(3) 0.17480(6) 0.0191(4) Uani 1 1 d . . . . .
H6 H 0.654640 0.781659 0.173629 0.023 Uiso 1 1 calc R U . . .
C8 C 0.62185(11) 0.7508(3) 0.24298(6) 0.0197(4) Uani 1 1 d . . . . .
H8A H 0.600369 0.833719 0.262227 0.024 Uiso 1 1 calc R U . . .
H8B H 0.666928 0.802341 0.235697 0.024 Uiso 1 1 calc R U . . .
C9 C 0.63205(12) 0.5652(3) 0.26142(6) 0.0226(5) Uani 1 1 d . . . . .
H9A H 0.655653 0.579693 0.286844 0.027 Uiso 1 1 calc R U . . .
H9B H 0.586846 0.508773 0.266408 0.027 Uiso 1 1 calc R U . . .
C11 C 0.59447(11) 0.2549(3) 0.18119(6) 0.0192(4) Uani 1 1 d . . . . .
C12 C 0.61733(11) 0.2740(3) 0.14253(6) 0.0219(5) Uani 1 1 d . . . . .
C14 C 0.52495(11) 0.2226(3) 0.18714(7) 0.0234(5) Uani 1 1 d . . . . .
H14 H 0.507945 0.209305 0.213005 0.028 Uiso 1 1 calc R U . . .
C15 C 0.48031(12) 0.2096(3) 0.15576(7) 0.0297(5) Uani 1 1 d . . . . .
H15 H 0.432906 0.189869 0.160358 0.036 Uiso 1 1 calc R U . . .
C16 C 0.50410(13) 0.2250(3) 0.11785(7) 0.0300(5) Uani 1 1 d . . . . .
H16 H 0.473331 0.214297 0.096459 0.036 Uiso 1 1 calc R U . . .
C17 C 0.57323(12) 0.2563(3) 0.11123(7) 0.0265(5) Uani 1 1 d . . . . .
H17 H 0.590111 0.265563 0.085255 0.032 Uiso 1 1 calc R U . . .
C18 C 0.49601(11) 0.7318(3) 0.13832(6) 0.0202(4) Uani 1 1 d . . . . .
C19 C 0.45951(11) 0.7313(3) 0.10284(6) 0.0216(5) Uani 1 1 d . . . . .
C20 C 0.49793(12) 0.7422(3) 0.06849(6) 0.0224(5) Uani 1 1 d . . . . .
H20 H 0.474000 0.740308 0.044313 0.027 Uiso 1 1 calc R U . . .
C21 C 0.65197(14) 0.9426(4) 0.02803(7) 0.0386(7) Uani 1 1 d . . . . .
H21A H 0.620191 1.045931 0.027183 0.058 Uiso 1 1 calc R U . . .
H21B H 0.681069 0.944315 0.004693 0.058 Uiso 1 1 calc R U . . .
H21C H 0.680680 0.951842 0.051452 0.058 Uiso 1 1 calc R U . . .
C22 C 0.66127(13) 0.6026(4) 0.02841(7) 0.0387(7) Uani 1 1 d . . . . .
H22A H 0.689036 0.608705 0.004577 0.058 Uiso 1 1 calc R U . . .
H22B H 0.635513 0.487995 0.028758 0.058 Uiso 1 1 calc R U . . .
H22C H 0.691258 0.608282 0.051348 0.058 Uiso 1 1 calc R U . . .
C23 C 0.38039(11) 0.7196(3) 0.10231(7) 0.0262(5) Uani 1 1 d . . . . .
C30 C 0.34903(12) 0.8773(4) 0.12587(8) 0.0368(6) Uani 1 1 d . . . . .
H30A H 0.299066 0.864887 0.126232 0.055 Uiso 1 1 calc R U . . .
H30B H 0.361488 0.993534 0.113689 0.055 Uiso 1 1 calc R U . . .
H30C H 0.366543 0.873955 0.152711 0.055 Uiso 1 1 calc R U . . .
C31 C 0.35161(13) 0.7319(4) 0.06062(8) 0.0383(7) Uani 1 1 d . . . . .
H31A H 0.370452 0.632618 0.044753 0.057 Uiso 1 1 calc R U . . .
H31B H 0.364419 0.849201 0.049046 0.057 Uiso 1 1 calc R U . . .
H31C H 0.301596 0.721653 0.061452 0.057 Uiso 1 1 calc R U . . .
C32 C 0.35708(12) 0.5366(4) 0.11956(8) 0.0335(6) Uani 1 1 d . . . . .
H32A H 0.306950 0.533250 0.120715 0.050 Uiso 1 1 calc R U . . .
H32B H 0.375818 0.522871 0.145976 0.050 Uiso 1 1 calc R U . . .
H32C H 0.373591 0.436852 0.103000 0.050 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
S1 O3 1.4313(15) . ?
S1 O4 1.4360(16) . ?
S1 N1 1.5932(19) . ?
S1 C11 1.789(2) . ?
O1 N3 1.230(2) . ?
O2 N3 1.225(2) . ?
O5 C18 1.355(3) . ?
O5 H5 0.8400 . ?
N1 C9 1.472(3) . ?
N1 H1 0.8800 . ?
N2 C6 1.277(3) . ?
N2 C8 1.462(3) . ?
N3 C12 1.472(3) . ?
C1 C2 1.534(3) . ?
C1 H1D 0.9800 . ?
C1 H1E 0.9800 . ?
C1 H1F 0.9800 . ?
C2 C22 1.534(4) . ?
C2 C21 1.537(3) . ?
C2 C3 1.539(3) . ?
C3 C4 1.389(3) . ?
C3 C20 1.399(3) . ?
C4 C5 1.396(3) . ?
C4 H4 0.9500 . ?
C5 C18 1.411(3) . ?
C5 C6 1.462(3) . ?
C6 H6 0.9500 . ?
C8 C9 1.513(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C11 C14 1.393(3) . ?
C11 C12 1.403(3) . ?
C12 C17 1.380(3) . ?
C14 C15 1.386(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.382(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.388(4) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C19 1.407(3) . ?
C19 C20 1.396(3) . ?
C19 C23 1.548(3) . ?
C20 H20 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C31 1.535(3) . ?
C23 C32 1.536(3) . ?
C23 C30 1.537(3) . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 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 S1 O4 120.29(10) . . ?
O3 S1 N1 107.12(9) . . ?
O4 S1 N1 107.80(10) . . ?
O3 S1 C11 105.19(10) . . ?
O4 S1 C11 105.24(10) . . ?
N1 S1 C11 111.11(10) . . ?
C18 O5 H5 109.5 . . ?
C9 N1 S1 123.34(15) . . ?
C9 N1 H1 118.3 . . ?
S1 N1 H1 118.3 . . ?
C6 N2 C8 118.15(18) . . ?
O2 N3 O1 123.98(19) . . ?
O2 N3 C12 117.43(19) . . ?
O1 N3 C12 118.55(18) . . ?
C2 C1 H1D 109.5 . . ?
C2 C1 H1E 109.5 . . ?
H1D C1 H1E 109.5 . . ?
C2 C1 H1F 109.5 . . ?
H1D C1 H1F 109.5 . . ?
H1E C1 H1F 109.5 . . ?
C1 C2 C22 108.28(19) . . ?
C1 C2 C21 108.3(2) . . ?
C22 C2 C21 109.1(2) . . ?
C1 C2 C3 112.84(18) . . ?
C22 C2 C3 108.94(19) . . ?
C21 C2 C3 109.31(19) . . ?
C4 C3 C20 117.1(2) . . ?
C4 C3 C2 119.2(2) . . ?
C20 C3 C2 123.72(19) . . ?
C3 C4 C5 121.3(2) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C4 C5 C18 120.02(19) . . ?
C4 C5 C6 118.6(2) . . ?
C18 C5 C6 121.34(19) . . ?
N2 C6 C5 122.4(2) . . ?
N2 C6 H6 118.8 . . ?
C5 C6 H6 118.8 . . ?
N2 C8 C9 111.27(17) . . ?
N2 C8 H8A 109.4 . . ?
C9 C8 H8A 109.4 . . ?
N2 C8 H8B 109.4 . . ?
C9 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
N1 C9 C8 111.51(17) . . ?
N1 C9 H9A 109.3 . . ?
C8 C9 H9A 109.3 . . ?
N1 C9 H9B 109.3 . . ?
C8 C9 H9B 109.3 . . ?
H9A C9 H9B 108.0 . . ?
C14 C11 C12 117.7(2) . . ?
C14 C11 S1 116.71(17) . . ?
C12 C11 S1 125.27(17) . . ?
C17 C12 C11 121.5(2) . . ?
C17 C12 N3 116.07(19) . . ?
C11 C12 N3 122.37(19) . . ?
C15 C14 C11 120.8(2) . . ?
C15 C14 H14 119.6 . . ?
C11 C14 H14 119.6 . . ?
C16 C15 C14 120.6(2) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C17 119.6(2) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 H16 120.2 . . ?
C12 C17 C16 119.7(2) . . ?
C12 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
O5 C18 C19 120.1(2) . . ?
O5 C18 C5 119.60(19) . . ?
C19 C18 C5 120.27(19) . . ?
C20 C19 C18 117.0(2) . . ?
C20 C19 C23 122.0(2) . . ?
C18 C19 C23 121.1(2) . . ?
C19 C20 C3 124.3(2) . . ?
C19 C20 H20 117.9 . . ?
C3 C20 H20 117.9 . . ?
C2 C21 H21A 109.5 . . ?
C2 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C2 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C2 C22 H22A 109.5 . . ?
C2 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C2 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C31 C23 C32 107.4(2) . . ?
C31 C23 C30 107.3(2) . . ?
C32 C23 C30 109.8(2) . . ?
C31 C23 C19 111.90(19) . . ?
C32 C23 C19 109.87(19) . . ?
C30 C23 C19 110.5(2) . . ?
C23 C30 H30A 109.5 . . ?
C23 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C23 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C23 C31 H31A 109.5 . . ?
C23 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C23 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C23 C32 H32A 109.5 . . ?
C23 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C23 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 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
_geom_hbond_publ_flag
O5 H5 N2 0.84 1.82 2.582(2) 149.4 . yes
N1 H1 O4 0.88 2.03 2.885(2) 163.6 6_765 yes

_refine_diff_density_max         0.646
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.054



####################################################################### 
# 
# 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_Alyson2_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 2088572'
loop_
_audit_author_name
_audit_author_address
'Xavier Ottenwaelder' 'Concordia University'
_audit_update_record             
;
2021-06-07 deposited with the CCDC.	2021-08-02 downloaded from the CCDC.
;

_vrf_PLAT220_Alyson2_0ma_a       
;
RESPONSE: A slight disorder (10%) of one tert-butyl group was 
not resolved.
;

_vrf_PLAT911_Alyson2_0ma_a       
;
RESPONSE: Some frames with a bad background were not integrated.
;

_vrf_PLAT912_Alyson2_0ma_a       
;
RESPONSE: Some frames with a bad background were not integrated.
;


_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H29 N3 Ni O4 S'
_chemical_formula_sum            'C23 H29 N3 Ni O4 S'
_chemical_formula_weight         502.26

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'
Ni Ni -3.0029 0.5091 '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/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   16.3521(12)
_cell_length_b                   12.6368(9)
_cell_length_c                   11.7356(9)
_cell_angle_alpha                90
_cell_angle_beta                 106.319(4)
_cell_angle_gamma                90
_cell_volume                     2327.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    9993
_cell_measurement_theta_min      2.82
_cell_measurement_theta_max      67.89

_exptl_crystal_description       plate
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_F_000             1056
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.297
_exptl_crystal_size_mid          0.127
_exptl_crystal_size_min          0.027
_exptl_absorpt_coefficient_mu    2.329
_shelx_estimated_absorpt_T_min   0.545
_shelx_estimated_absorpt_T_max   0.940
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6154
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_process_details   'SADABS-2016/2 - Bruker AXS'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            32384
_diffrn_reflns_av_unetI/netI     0.0417
_diffrn_reflns_av_R_equivalents  0.0751
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.816
_diffrn_reflns_theta_max         68.242
_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             4203
_reflns_number_gt                3737
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0428P)²+2.0333P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4203
_refine_ls_number_parameters     296
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0349
_refine_ls_wR_factor_ref         0.0944
_refine_ls_wR_factor_gt          0.0907
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_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
Ni1 Ni 0.66069(2) 0.38797(3) 0.32237(3) 0.01244(12) Uani 1 1 d . . . . .
S1 S 0.57621(3) 0.27609(4) 0.48972(4) 0.01477(13) Uani 1 1 d . . . . .
O1 O 0.81496(9) 0.31366(13) 0.45646(14) 0.0241(4) Uani 1 1 d . . . . .
O2 O 0.74912(8) 0.42285(11) 0.26197(12) 0.0144(3) Uani 1 1 d . . . . .
O3 O 0.61001(10) 0.17396(11) 0.47294(13) 0.0209(3) Uani 1 1 d . . . . .
O4 O 0.50032(9) 0.27898(12) 0.52927(13) 0.0205(3) Uani 1 1 d . . . . .
N1 N 0.74389(10) 0.34284(13) 0.45862(15) 0.0157(4) Uani 1 1 d . . . . .
N2 N 0.56591(10) 0.34515(13) 0.37375(15) 0.0157(4) Uani 1 1 d . . . . .
N3 N 0.58009(10) 0.46279(13) 0.20713(14) 0.0123(3) Uani 1 1 d . . . . .
C1 C 0.73550(12) 0.36305(16) 0.57645(18) 0.0151(4) Uani 1 1 d . . . . .
C2 C 0.80324(13) 0.40661(16) 0.66281(19) 0.0185(4) Uani 1 1 d . . . . .
H2 H 0.855508 0.421815 0.645851 0.022 Uiso 1 1 calc R U . . .
C3 C 0.79345(13) 0.42769(17) 0.77462(19) 0.0203(5) Uani 1 1 d . . . . .
H3 H 0.838823 0.459312 0.833763 0.024 Uiso 1 1 calc R U . . .
C4 C 0.71771(14) 0.40279(17) 0.8004(2) 0.0200(4) Uani 1 1 d . . . . .
H4 H 0.711726 0.417247 0.877140 0.024 Uiso 1 1 calc R U . . .
C5 C 0.65063(13) 0.35675(16) 0.71435(19) 0.0167(4) Uani 1 1 d . . . . .
H5 H 0.599548 0.338058 0.732852 0.020 Uiso 1 1 calc R U . . .
C6 C 0.65870(12) 0.33825(15) 0.60114(18) 0.0147(4) Uani 1 1 d . . . . .
C7 C 0.49634(13) 0.42390(17) 0.33927(19) 0.0177(4) Uani 1 1 d . . . . .
H7A H 0.510404 0.488795 0.388130 0.021 Uiso 1 1 calc R U . . .
H7AB H 0.441990 0.394421 0.346750 0.021 Uiso 1 1 calc R U . . .
C8 C 0.49176(12) 0.44592(17) 0.21078(18) 0.0162(4) Uani 1 1 d . . . . .
H8A H 0.466029 0.385143 0.160082 0.019 Uiso 1 1 calc R U . . .
H8AB H 0.456818 0.509648 0.182155 0.019 Uiso 1 1 calc R U . . .
C9 C 0.59622(12) 0.53053(15) 0.13370(17) 0.0132(4) Uani 1 1 d . . . . .
H9 H 0.549366 0.569202 0.085453 0.016 Uiso 1 1 calc R U . . .
C10 C 0.67825(12) 0.55227(15) 0.11880(17) 0.0125(4) Uani 1 1 d . . . . .
C11 C 0.68426(13) 0.63608(16) 0.04164(18) 0.0150(4) Uani 1 1 d . . . . .
H11 H 0.634694 0.675631 0.003627 0.018 Uiso 1 1 calc R U . . .
C12 C 0.76011(13) 0.66119(16) 0.02079(18) 0.0155(4) Uani 1 1 d . . . . .
C13 C 0.83112(12) 0.59700(16) 0.07586(18) 0.0148(4) Uani 1 1 d . . . . .
H13 H 0.883152 0.610775 0.057604 0.018 Uiso 1 1 calc R U . . .
C14 C 0.83024(12) 0.51569(15) 0.15434(17) 0.0124(4) Uani 1 1 d . . . . .
C15 C 0.75120(12) 0.49413(15) 0.18053(17) 0.0120(4) Uani 1 1 d . . . . .
C16 C 0.77106(13) 0.75713(17) -0.0530(2) 0.0200(5) Uani 1 1 d . . . . .
C17 C 0.68863(16) 0.8211(2) -0.0961(3) 0.0374(6) Uani 1 1 d . . . . .
H17A H 0.699348 0.884652 -0.137669 0.056 Uiso 1 1 calc R U . . .
H17B H 0.668850 0.841897 -0.027902 0.056 Uiso 1 1 calc R U . . .
H17C H 0.644936 0.777837 -0.150467 0.056 Uiso 1 1 calc R U . . .
C18 C 0.80123(19) 0.7244(2) -0.1581(2) 0.0364(6) Uani 1 1 d . . . . .
H18A H 0.805283 0.786897 -0.205587 0.055 Uiso 1 1 calc R U . . .
H18B H 0.760625 0.674030 -0.206993 0.055 Uiso 1 1 calc R U . . .
H18C H 0.857358 0.690861 -0.129949 0.055 Uiso 1 1 calc R U . . .
C19 C 0.83755(18) 0.8321(2) 0.0277(2) 0.0355(6) Uani 1 1 d . . . . .
H19A H 0.843698 0.895600 -0.017082 0.053 Uiso 1 1 calc R U . . .
H19B H 0.892563 0.795707 0.054544 0.053 Uiso 1 1 calc R U . . .
H19C H 0.818472 0.852332 0.096683 0.053 Uiso 1 1 calc R U . . .
C20 C 0.91200(12) 0.45425(16) 0.21652(18) 0.0141(4) Uani 1 1 d . . . . .
C21 C 0.89815(14) 0.33438(16) 0.2010(2) 0.0211(5) Uani 1 1 d . . . . .
H21A H 0.951680 0.297460 0.238315 0.032 Uiso 1 1 calc R U . . .
H21B H 0.879446 0.317176 0.116149 0.032 Uiso 1 1 calc R U . . .
H21C H 0.854492 0.311984 0.238481 0.032 Uiso 1 1 calc R U . . .
C22 C 0.98595(13) 0.48284(18) 0.1656(2) 0.0219(5) Uani 1 1 d . . . . .
H22A H 1.036404 0.441389 0.206023 0.033 Uiso 1 1 calc R U . . .
H22B H 0.998833 0.558440 0.177701 0.033 Uiso 1 1 calc R U . . .
H22C H 0.969829 0.466954 0.080399 0.033 Uiso 1 1 calc R U . . .
C23 C 0.94001(13) 0.48218(17) 0.34978(19) 0.0195(4) Uani 1 1 d . . . . .
H23A H 0.992034 0.443052 0.389104 0.029 Uiso 1 1 calc R U . . .
H23B H 0.894702 0.462892 0.385618 0.029 Uiso 1 1 calc R U . . .
H23C H 0.951113 0.558342 0.359317 0.029 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
Ni1 O2 1.8339(14) . ?
Ni1 N3 1.8597(16) . ?
Ni1 N1 1.8736(17) . ?
Ni1 N2 1.8931(17) . ?
S1 O3 1.4390(15) . ?
S1 O4 1.4423(15) . ?
S1 N2 1.5853(17) . ?
S1 C6 1.776(2) . ?
O1 N1 1.226(2) . ?
O2 C15 1.321(2) . ?
N1 C1 1.450(3) . ?
N2 C7 1.480(3) . ?
N3 C9 1.293(3) . ?
N3 C8 1.472(2) . ?
C1 C2 1.388(3) . ?
C1 C6 1.401(3) . ?
C2 C3 1.392(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.391(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.393(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.391(3) . ?
C5 H5 0.9500 . ?
C7 C8 1.514(3) . ?
C7 H7A 0.9900 . ?
C7 H7AB 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8AB 0.9900 . ?
C9 C10 1.427(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.415(3) . ?
C10 C15 1.415(3) . ?
C11 C12 1.367(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.415(3) . ?
C12 C16 1.529(3) . ?
C13 C14 1.383(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.436(3) . ?
C14 C20 1.541(3) . ?
C16 C18 1.509(3) . ?
C16 C17 1.531(3) . ?
C16 C19 1.548(3) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.535(3) . ?
C20 C22 1.535(3) . ?
C20 C23 1.542(3) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 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
O2 Ni1 N3 94.10(7) . . ?
O2 Ni1 N1 86.60(7) . . ?
N3 Ni1 N1 166.33(7) . . ?
O2 Ni1 N2 175.40(7) . . ?
N3 Ni1 N2 84.29(7) . . ?
N1 Ni1 N2 95.98(7) . . ?
O3 S1 O4 117.71(9) . . ?
O3 S1 N2 109.18(9) . . ?
O4 S1 N2 111.64(9) . . ?
O3 S1 C6 104.83(9) . . ?
O4 S1 C6 107.21(9) . . ?
N2 S1 C6 105.31(9) . . ?
C15 O2 Ni1 128.83(12) . . ?
O1 N1 C1 114.63(16) . . ?
O1 N1 Ni1 122.61(14) . . ?
C1 N1 Ni1 121.31(13) . . ?
C7 N2 S1 119.54(14) . . ?
C7 N2 Ni1 110.85(13) . . ?
S1 N2 Ni1 122.13(10) . . ?
C9 N3 C8 120.04(16) . . ?
C9 N3 Ni1 125.84(14) . . ?
C8 N3 Ni1 113.94(12) . . ?
C2 C1 C6 121.03(19) . . ?
C2 C1 N1 119.76(18) . . ?
C6 C1 N1 119.22(18) . . ?
C1 C2 C3 119.00(19) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
C4 C3 C2 120.5(2) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 120.3(2) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C6 C5 C4 119.75(19) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C5 C6 C1 119.39(18) . . ?
C5 C6 S1 121.41(15) . . ?
C1 C6 S1 119.08(16) . . ?
N2 C7 C8 102.41(16) . . ?
N2 C7 H7A 111.3 . . ?
C8 C7 H7A 111.3 . . ?
N2 C7 H7AB 111.3 . . ?
C8 C7 H7AB 111.3 . . ?
H7A C7 H7AB 109.2 . . ?
N3 C8 C7 106.33(16) . . ?
N3 C8 H8A 110.5 . . ?
C7 C8 H8A 110.5 . . ?
N3 C8 H8AB 110.5 . . ?
C7 C8 H8AB 110.5 . . ?
H8A C8 H8AB 108.7 . . ?
N3 C9 C10 125.71(18) . . ?
N3 C9 H9 117.1 . . ?
C10 C9 H9 117.1 . . ?
C11 C10 C15 121.09(17) . . ?
C11 C10 C9 117.33(17) . . ?
C15 C10 C9 121.57(17) . . ?
C12 C11 C10 121.19(18) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C11 C12 C13 117.03(18) . . ?
C11 C12 C16 122.80(18) . . ?
C13 C12 C16 120.09(18) . . ?
C14 C13 C12 124.71(18) . . ?
C14 C13 H13 117.6 . . ?
C12 C13 H13 117.6 . . ?
C13 C14 C15 117.51(17) . . ?
C13 C14 C20 121.32(17) . . ?
C15 C14 C20 121.09(17) . . ?
O2 C15 C10 122.36(17) . . ?
O2 C15 C14 119.47(17) . . ?
C10 C15 C14 118.16(17) . . ?
C18 C16 C12 111.25(18) . . ?
C18 C16 C17 109.5(2) . . ?
C12 C16 C17 111.95(18) . . ?
C18 C16 C19 109.5(2) . . ?
C12 C16 C19 108.20(18) . . ?
C17 C16 C19 106.3(2) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 C22 106.97(17) . . ?
C21 C20 C14 111.20(16) . . ?
C22 C20 C14 111.74(16) . . ?
C21 C20 C23 109.78(17) . . ?
C22 C20 C23 107.41(17) . . ?
C14 C20 C23 109.63(16) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

_refine_diff_density_max         0.743
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.063



