# Electronic Supplementary Material (ESI) for Metallomics.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_QINXIUYING-Cu-2
_database_code_depnum_ccdc_archive 'CCDC 1565798'
_audit_update_record             
;
2017-07-31 deposited with the CCDC.	2019-11-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ' C20 H24 Br2 Cu2 N2 O12 S2, 2(H2 O) '
_chemical_formula_sum            'C20 H28 Br2 Cu2 N2 O14 S2'
_chemical_formula_weight         871.46

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'
Br Br -0.2901 2.4595 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/c  '

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

_cell_length_a                   12.248(3)
_cell_length_b                   7.6422(18)
_cell_length_c                   15.829(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.923(4)
_cell_angle_gamma                90.00
_cell_volume                     1431.7(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4437
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      26.38

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.022
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             868
_exptl_absorpt_coefficient_mu    4.493
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.241
_exptl_absorpt_correction_T_max  0.340
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7738
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_av_sigmaI/netI    0.0475
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.66
_diffrn_reflns_theta_max         25.35
_reflns_number_total             2605
_reflns_number_gt                2267
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0459P)²+1.1448P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0084(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2605
_refine_ls_number_parameters     166
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0332
_refine_ls_wR_factor_ref         0.0896
_refine_ls_wR_factor_gt          0.0865
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.75776(3) 0.00518(5) 0.80647(3) 0.02910(16) Uani 1 1 d . . .
Cu1 Cu 0.18196(3) 0.16858(5) 0.53100(3) 0.01520(16) Uani 1 1 d . . .
S1 S -0.04041(6) 0.20986(10) 0.59594(5) 0.0147(2) Uani 1 1 d . . .
O1 O 0.5280(2) 0.2631(4) 0.50360(17) 0.0296(6) Uani 1 1 d . . .
O2 O 0.33514(19) 0.1758(3) 0.52752(15) 0.0239(6) Uani 1 1 d . . .
O3 O 0.0386(2) 0.2670(4) 0.54518(18) 0.0320(7) Uani 1 1 d . . .
O4 O -0.0915(2) 0.3590(3) 0.62635(18) 0.0310(6) Uani 1 1 d . . .
O5 O -0.1214(2) 0.0858(4) 0.54887(18) 0.0357(7) Uani 1 1 d . . .
O1W O 0.14735(8) 0.29815(13) 0.41897(6) 0.0247(6) Uani 1 1 d . . .
H1WA H 0.0965 0.3740 0.4190 0.037 Uiso 1 1 d R . .
H1WB H 0.1237 0.2274 0.3767 0.037 Uiso 1 1 d R . .
N1 N 0.21272(11) 0.03108(16) 0.63816(7) 0.0145(6) Uani 1 1 d R . .
C1 C 0.63125(8) 0.31888(14) 0.48647(6) 0.0319(9) Uani 1 1 d R . .
H1A H 0.6680 0.4016 0.5302 0.048 Uiso 1 1 calc R . .
H1B H 0.6157 0.3730 0.4299 0.048 Uiso 1 1 calc R . .
H1C H 0.6797 0.2196 0.4877 0.048 Uiso 1 1 calc R . .
C2 C 0.53200(8) 0.17953(14) 0.57990(6) 0.0174(7) Uani 1 1 d R . .
C3 C 0.62962(8) 0.14137(14) 0.64340(6) 0.0204(8) Uani 1 1 d R . .
H3 H 0.6999 0.1714 0.6355 0.024 Uiso 1 1 calc R . .
C4 C 0.62113(8) 0.05713(14) 0.71956(6) 0.0199(7) Uani 1 1 d R . .
C5 C 0.51922(8) 0.00859(14) 0.73321(6) 0.0191(7) Uani 1 1 d R . .
H5 H 0.5159 -0.0501 0.7840 0.023 Uiso 1 1 calc R . .
C6 C 0.41883(8) 0.04979(14) 0.66816(6) 0.0151(7) Uani 1 1 d R . .
C7 C 0.42273(8) 0.13409(14) 0.59077(6) 0.0167(7) Uani 1 1 d R . .
C8 C 0.31259(8) -0.00518(14) 0.68486(6) 0.0154(7) Uani 1 1 d R . .
H8 H 0.3174 -0.0734 0.7343 0.018 Uiso 1 1 calc R . .
C9 C 0.11660(8) -0.0410(2) 0.66759(8) 0.0185(7) Uani 1 1 d R . .
H9A H 0.1453 -0.1136 0.7188 0.022 Uiso 1 1 calc R . .
H9B H 0.0712 -0.1144 0.6218 0.022 Uiso 1 1 calc R . .
C10 C 0.04282(9) 0.1022(2) 0.68974(8) 0.0194(7) Uani 1 1 d R . .
H10A H 0.0906 0.1877 0.7272 0.023 Uiso 1 1 calc R . .
H10B H -0.0067 0.0516 0.7222 0.023 Uiso 1 1 calc R . .
O2W O 0.3376(2) 0.1696(4) 0.86239(19) 0.0361(7) Uani 1 1 d G . .
H2WA H 0.2690 0.1759 0.8643 0.054 Uiso 1 1 d G . .
H2WB H 0.3517 0.2519 0.8306 0.054 Uiso 1 1 d G . .


_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
Br1 C4 1.9144 . ?
Cu1 O2 1.892(2) . ?
Cu1 N1 1.9479 . ?
Cu1 O3 1.975(2) . ?
Cu1 O1W 1.9793(10) . ?
Cu1 O5 2.333(3) 3_556 ?
S1 O5 1.434(3) . ?
S1 O4 1.441(3) . ?
S1 O3 1.475(3) . ?
S1 C10 1.7723(12) . ?
O1 C2 1.356(3) . ?
O1 C1 1.425(3) . ?
O2 C7 1.304(2) . ?
O5 Cu1 2.333(3) 3_556 ?
O1W H1WA 0.8507 . ?
O1W H1WB 0.8503 . ?
N1 C8 1.2861 . ?
N1 C9 1.4795 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.3807 . ?
C2 C7 1.4352 . ?
C3 C4 1.3941 . ?
C3 H3 0.9300 . ?
C4 C5 1.3715 . ?
C5 C6 1.4210 . ?
C5 H5 0.9300 . ?
C6 C7 1.3958 . ?
C6 C8 1.4550 . ?
C8 H8 0.9300 . ?
C9 C10 1.5168 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
O2W H2WA 0.8498 . ?
O2W H2WB 0.8504 . ?

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 N1 94.02(8) . . ?
O2 Cu1 O3 155.42(12) . . ?
N1 Cu1 O3 94.86(9) . . ?
O2 Cu1 O1W 86.82(8) . . ?
N1 Cu1 O1W 177.23(7) . . ?
O3 Cu1 O1W 85.40(8) . . ?
O2 Cu1 O5 100.82(11) . 3_556 ?
N1 Cu1 O5 89.17(8) . 3_556 ?
O3 Cu1 O5 102.17(12) . 3_556 ?
O1W Cu1 O5 88.08(8) . 3_556 ?
O5 S1 O4 113.23(17) . . ?
O5 S1 O3 112.08(19) . . ?
O4 S1 O3 110.52(17) . . ?
O5 S1 C10 107.46(14) . . ?
O4 S1 C10 107.02(13) . . ?
O3 S1 C10 106.09(11) . . ?
C2 O1 C1 118.70(19) . . ?
C7 O2 Cu1 126.61(16) . . ?
S1 O3 Cu1 132.58(17) . . ?
S1 O5 Cu1 155.94(18) . 3_556 ?
Cu1 O1W H1WA 109.2 . . ?
Cu1 O1W H1WB 109.7 . . ?
H1WA O1W H1WB 109.4 . . ?
C8 N1 C9 117.1 . . ?
C8 N1 Cu1 123.97(5) . . ?
C9 N1 Cu1 118.9 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 125.01(11) . . ?
O1 C2 C7 113.57(11) . . ?
C3 C2 C7 121.4 . . ?
C2 C3 C4 118.9 . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C5 C4 C3 122.3 . . ?
C5 C4 Br1 119.6 . . ?
C3 C4 Br1 118.1 . . ?
C4 C5 C6 118.6 . . ?
C4 C5 H5 120.7 . . ?
C6 C5 H5 120.7 . . ?
C7 C6 C5 121.3 . . ?
C7 C6 C8 121.8 . . ?
C5 C6 C8 116.9 . . ?
O2 C7 C6 125.38(11) . . ?
O2 C7 C2 117.19(11) . . ?
C6 C7 C2 117.4 . . ?
N1 C8 C6 126.6 . . ?
N1 C8 H8 116.7 . . ?
C6 C8 H8 116.7 . . ?
N1 C9 C10 112.0 . . ?
N1 C9 H9A 109.2 . . ?
C10 C9 H9A 109.2 . . ?
N1 C9 H9B 109.2 . . ?
C10 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
C9 C10 S1 112.93(5) . . ?
C9 C10 H10A 109.0 . . ?
S1 C10 H10A 109.0 . . ?
C9 C10 H10B 109.0 . . ?
S1 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
H2WA O2W H2WB 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 Cu1 O2 C7 -13.6(2) . . . . ?
O3 Cu1 O2 C7 97.4(3) . . . . ?
O1W Cu1 O2 C7 169.0(2) . . . . ?
O5 Cu1 O2 C7 -103.5(2) 3_556 . . . ?
O5 S1 O3 Cu1 -85.9(3) . . . . ?
O4 S1 O3 Cu1 146.8(2) . . . . ?
C10 S1 O3 Cu1 31.1(3) . . . . ?
O2 Cu1 O3 S1 -131.9(3) . . . . ?
N1 Cu1 O3 S1 -21.0(3) . . . . ?
O1W Cu1 O3 S1 156.2(3) . . . . ?
O5 Cu1 O3 S1 69.2(3) 3_556 . . . ?
O4 S1 O5 Cu1 178.4(4) . . . 3_556 ?
O3 S1 O5 Cu1 52.5(5) . . . 3_556 ?
C10 S1 O5 Cu1 -63.7(5) . . . 3_556 ?
O2 Cu1 N1 C8 7.68(14) . . . . ?
O3 Cu1 N1 C8 -149.38(14) . . . . ?
O1W Cu1 N1 C8 115.3(14) . . . . ?
O5 Cu1 N1 C8 108.48(13) 3_556 . . . ?
O2 Cu1 N1 C9 -170.71(8) . . . . ?
O3 Cu1 N1 C9 32.23(10) . . . . ?
O1W Cu1 N1 C9 -63.1(14) . . . . ?
O5 Cu1 N1 C9 -69.92(7) 3_556 . . . ?
C1 O1 C2 C3 -0.7(3) . . . . ?
C1 O1 C2 C7 178.39(17) . . . . ?
O1 C2 C3 C4 178.95(17) . . . . ?
C7 C2 C3 C4 -0.1 . . . . ?
C2 C3 C4 C5 0.9 . . . . ?
C2 C3 C4 Br1 179.8 . . . . ?
C3 C4 C5 C6 -1.6 . . . . ?
Br1 C4 C5 C6 179.5 . . . . ?
C4 C5 C6 C7 1.5 . . . . ?
C4 C5 C6 C8 179.5 . . . . ?
Cu1 O2 C7 C6 10.9(3) . . . . ?
Cu1 O2 C7 C2 -168.77(13) . . . . ?
C5 C6 C7 O2 179.54(16) . . . . ?
C8 C6 C7 O2 1.62(16) . . . . ?
C5 C6 C7 C2 -0.8 . . . . ?
C8 C6 C7 C2 -178.7 . . . . ?
O1 C2 C7 O2 0.62(19) . . . . ?
C3 C2 C7 O2 179.77(14) . . . . ?
O1 C2 C7 C6 -179.10(15) . . . . ?
C3 C2 C7 C6 0.0 . . . . ?
C9 N1 C8 C6 179.4 . . . . ?
Cu1 N1 C8 C6 0.98(14) . . . . ?
C7 C6 C8 N1 -7.93(9) . . . . ?
C5 C6 C8 N1 174.06(9) . . . . ?
C8 N1 C9 C10 117.99(7) . . . . ?
Cu1 N1 C9 C10 -63.5 . . . . ?
N1 C9 C10 S1 73.01(5) . . . . ?
O5 S1 C10 C9 67.18(14) . . . . ?
O4 S1 C10 C9 -170.90(13) . . . . ?
O3 S1 C10 C9 -52.87(15) . . . . ?

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
O1W H1WA O4 0.85 2.16 2.756(3) 127.1 3_566
O2W H2WA O1W 0.85 1.92 2.714(3) 155.9 4_566
O2W H2WB Br1 0.85 2.96 3.671(3) 142.6 2_656
O1W H1WB O5 0.85 2.67 3.009(3) 105.2 3_556

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.593
_refine_diff_density_min         -0.901
_refine_diff_density_rms         0.110
####################################################################### 
# 
# 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_QINXIUYING-Co-1
_database_code_depnum_ccdc_archive 'CCDC 1565799'
_audit_update_record             
;
2017-07-31 deposited with the CCDC.	2019-11-01 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H20 Br Co N3 O6 S, C2 H6 O'
_chemical_formula_sum            'C24 H26 Br Co N3 O7 S'
_chemical_formula_weight         639.38

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   15.5234(7)
_cell_length_b                   19.2687(5)
_cell_length_c                   19.1761(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.933(5)
_cell_angle_gamma                90.00
_cell_volume                     5282.5(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4307
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.608
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2600
_exptl_absorpt_coefficient_mu    2.290
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.803
_exptl_absorpt_correction_T_max  0.892
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
ï?1/2ï?1/2
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16529
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_sigmaI/netI    0.0372
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.32
_diffrn_reflns_theta_max         26.37
_reflns_number_total             5385
_reflns_number_gt                4202
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0462P)²+11.5939P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5385
_refine_ls_number_parameters     343
_refine_ls_number_restraints     1018
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0428
_refine_ls_wR_factor_ref         0.1103
_refine_ls_wR_factor_gt          0.0998
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      0.967
_refine_ls_shift/su_max          0.002
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.73875(4) -0.05415(2) 0.84418(3) 0.0903(2) Uani 1 1 d U . .
Co1 Co 0.92333(3) 0.284807(19) 1.02543(2) 0.02889(11) Uani 1 1 d DU . .
S1 S 1.11772(5) 0.30553(4) 1.17727(4) 0.03673(19) Uani 1 1 d U . .
O1 O 0.69455(18) 0.21490(13) 0.80667(13) 0.0545(6) Uani 1 1 d U . .
O2 O 0.81271(14) 0.24347(10) 0.94310(11) 0.0359(5) Uani 1 1 d U . .
O3 O 1.03579(14) 0.33162(11) 1.11362(11) 0.0398(5) Uani 1 1 d U . .
O4 O 1.20362(17) 0.32526(15) 1.17149(15) 0.0623(7) Uani 1 1 d U . .
O5 O 1.11261(18) 0.32390(13) 1.24837(12) 0.0542(6) Uani 1 1 d U . .
O1W O 0.83837(15) 0.32706(11) 1.07842(11) 0.0389(5) Uani 1 1 d DU . .
H1WA H 0.7954(17) 0.3002(13) 1.0789(17) 0.058 Uiso 1 1 d D . .
H1WB H 0.8687(16) 0.3403(17) 1.1234(8) 0.058 Uiso 1 1 d D . .
O6 O 0.9399(2) 0.1100(2) 0.71689(17) 0.0820(10) Uani 1 1 d U . .
H6 H 0.9906 0.1297 0.7305 0.123 Uiso 1 1 calc R . .
N1 N 0.94908(17) 0.18975(13) 1.08253(13) 0.0348(5) Uani 1 1 d U . .
N2 N 1.01919(18) 0.26531(13) 0.96959(13) 0.0363(6) Uani 1 1 d U . .
N3 N 0.91553(19) 0.37938(13) 0.96410(14) 0.0385(6) Uani 1 1 d U . .
C1 C 0.6394(3) 0.2020(2) 0.7286(2) 0.0683(12) Uani 1 1 d U . .
H1A H 0.6156 0.2451 0.7033 0.102 Uiso 1 1 calc R . .
H1B H 0.5882 0.1720 0.7243 0.102 Uiso 1 1 calc R . .
H1C H 0.6775 0.1801 0.7056 0.102 Uiso 1 1 calc R . .
C2 C 0.7352(2) 0.15953(18) 0.85094(17) 0.0405(7) Uani 1 1 d U . .
C3 C 0.7180(3) 0.0910(2) 0.8288(2) 0.0523(9) Uani 1 1 d U . .
H3 H 0.6760 0.0800 0.7802 0.063 Uiso 1 1 calc R . .
C4 C 0.7637(3) 0.03863(19) 0.8793(2) 0.0544(9) Uani 1 1 d U . .
C5 C 0.8255(3) 0.05321(17) 0.9505(2) 0.0500(8) Uani 1 1 d U . .
H5 H 0.8550 0.0172 0.9835 0.060 Uiso 1 1 calc R . .
C6 C 0.8451(2) 0.12279(16) 0.97462(18) 0.0380(7) Uani 1 1 d U . .
C7 C 0.8002(2) 0.17769(16) 0.92554(17) 0.0345(6) Uani 1 1 d U . .
C8 C 0.9111(2) 0.13328(16) 1.05175(18) 0.0390(7) Uani 1 1 d U . .
H8 H 0.9276 0.0940 1.0823 0.047 Uiso 1 1 calc R . .
C9 C 1.0149(3) 0.18650(18) 1.16197(17) 0.0483(8) Uani 1 1 d U . .
H9A H 1.0206 0.1388 1.1794 0.058 Uiso 1 1 calc R . .
H9B H 0.9905 0.2137 1.1928 0.058 Uiso 1 1 calc R . .
C10 C 1.1110(2) 0.21393(17) 1.17193(18) 0.0465(8) Uani 1 1 d U . .
H10A H 1.1256 0.1985 1.1297 0.056 Uiso 1 1 calc R . .
H10B H 1.1575 0.1945 1.2178 0.056 Uiso 1 1 calc R . .
C11 C 1.0655(2) 0.2080(2) 0.9677(2) 0.0500(8) Uani 1 1 d U . .
H11 H 1.0531 0.1679 0.9892 0.060 Uiso 1 1 calc R . .
C12 C 1.1316(3) 0.2044(2) 0.9355(2) 0.0624(10) Uani 1 1 d U . .
H12 H 1.1616 0.1627 0.9350 0.075 Uiso 1 1 calc R . .
C13 C 1.1515(3) 0.2625(2) 0.9048(2) 0.0613(10) Uani 1 1 d U . .
H13 H 1.1965 0.2612 0.8840 0.074 Uiso 1 1 calc R . .
C14 C 1.1042(3) 0.3242(2) 0.90451(19) 0.0517(9) Uani 1 1 d U . .
C15 C 1.1180(3) 0.3876(2) 0.8710(2) 0.0667(11) Uani 1 1 d U . .
H15 H 1.1638 0.3895 0.8512 0.080 Uiso 1 1 calc R . .
C16 C 1.0667(3) 0.4435(2) 0.8678(2) 0.0687(11) Uani 1 1 d U . .
H16 H 1.0776 0.4838 0.8457 0.082 Uiso 1 1 calc R . .
C17 C 0.9945(3) 0.44337(19) 0.8975(2) 0.0566(10) Uani 1 1 d U . .
C18 C 0.9361(3) 0.4992(2) 0.8920(2) 0.0692(11) Uani 1 1 d U . .
H18 H 0.9429 0.5399 0.8685 0.083 Uiso 1 1 calc R . .
C19 C 0.8690(3) 0.4950(2) 0.9206(2) 0.0673(11) Uani 1 1 d U . .
H19 H 0.8286 0.5320 0.9158 0.081 Uiso 1 1 calc R . .
C20 C 0.8615(3) 0.43339(18) 0.9577(2) 0.0520(9) Uani 1 1 d U . .
H20 H 0.8166 0.4310 0.9785 0.062 Uiso 1 1 calc R . .
C21 C 0.9813(2) 0.38360(17) 0.93396(16) 0.0412(7) Uani 1 1 d U . .
C22 C 1.0368(2) 0.32318(17) 0.93727(16) 0.0406(7) Uani 1 1 d U . .
C23 C 0.9202(4) 0.0944(3) 0.7796(3) 0.0947(16) Uani 1 1 d U . .
H23A H 0.8543 0.0828 0.7622 0.114 Uiso 1 1 calc R . .
H23B H 0.9303 0.1359 0.8104 0.114 Uiso 1 1 calc R . .
C24 C 0.9726(5) 0.0394(3) 0.8264(3) 0.113(2) Uani 1 1 d U . .
H24A H 0.9619 -0.0026 0.7973 0.169 Uiso 1 1 calc R . .
H24B H 0.9533 0.0329 0.8678 0.169 Uiso 1 1 calc R . .
H24C H 1.0380 0.0507 0.8457 0.169 Uiso 1 1 calc R . .


_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
Br1 C4 1.897(3) . ?
Co1 O2 1.991(2) . ?
Co1 N1 2.091(2) . ?
Co1 O3 2.103(2) . ?
Co1 O1W 2.116(2) . ?
Co1 N3 2.147(3) . ?
Co1 N2 2.178(2) . ?
S1 O4 1.432(3) . ?
S1 O5 1.441(2) . ?
S1 O3 1.466(2) . ?
S1 C10 1.769(3) . ?
O1 C2 1.356(4) . ?
O1 C1 1.427(4) . ?
O2 C7 1.306(3) . ?
O1W H1WA 0.848(9) . ?
O1W H1WB 0.846(9) . ?
O6 C23 1.384(5) . ?
O6 H6 0.8200 . ?
N1 C8 1.268(4) . ?
N1 C9 1.468(4) . ?
N2 C11 1.326(4) . ?
N2 C22 1.355(4) . ?
N3 C20 1.312(4) . ?
N3 C21 1.357(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.381(5) . ?
C2 C7 1.436(4) . ?
C3 C4 1.387(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.356(5) . ?
C5 C6 1.413(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.407(4) . ?
C6 C8 1.448(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.523(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.391(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.355(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.397(6) . ?
C13 H13 0.9300 . ?
C14 C22 1.415(5) . ?
C14 C15 1.434(6) . ?
C15 C16 1.327(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.441(6) . ?
C16 H16 0.9300 . ?
C17 C18 1.385(6) . ?
C17 C21 1.404(5) . ?
C18 C19 1.355(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.412(5) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 C22 1.435(5) . ?
C23 C24 1.422(7) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 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
O2 Co1 N1 89.69(9) . . ?
O2 Co1 O3 177.26(8) . . ?
N1 Co1 O3 91.44(9) . . ?
O2 Co1 O1W 91.63(8) . . ?
N1 Co1 O1W 96.51(9) . . ?
O3 Co1 O1W 85.77(8) . . ?
O2 Co1 N3 93.33(9) . . ?
N1 Co1 N3 171.48(10) . . ?
O3 Co1 N3 85.89(9) . . ?
O1W Co1 N3 91.37(10) . . ?
O2 Co1 N2 94.85(9) . . ?
N1 Co1 N2 94.50(10) . . ?
O3 Co1 N2 87.55(9) . . ?
O1W Co1 N2 167.25(9) . . ?
N3 Co1 N2 77.32(10) . . ?
O4 S1 O5 113.86(16) . . ?
O4 S1 O3 112.12(15) . . ?
O5 S1 O3 110.72(14) . . ?
O4 S1 C10 107.25(17) . . ?
O5 S1 C10 106.02(16) . . ?
O3 S1 C10 106.34(14) . . ?
C2 O1 C1 117.5(3) . . ?
C7 O2 Co1 126.02(18) . . ?
S1 O3 Co1 134.54(13) . . ?
Co1 O1W H1WA 114.3(18) . . ?
Co1 O1W H1WB 113.8(18) . . ?
H1WA O1W H1WB 108(2) . . ?
C23 O6 H6 109.5 . . ?
C8 N1 C9 117.1(3) . . ?
C8 N1 Co1 123.3(2) . . ?
C9 N1 Co1 119.6(2) . . ?
C11 N2 C22 117.7(3) . . ?
C11 N2 Co1 129.7(2) . . ?
C22 N2 Co1 112.4(2) . . ?
C20 N3 C21 118.2(3) . . ?
C20 N3 Co1 128.5(2) . . ?
C21 N3 Co1 113.1(2) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 125.0(3) . . ?
O1 C2 C7 114.0(3) . . ?
C3 C2 C7 121.0(3) . . ?
C2 C3 C4 119.8(3) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 121.3(3) . . ?
C5 C4 Br1 121.3(3) . . ?
C3 C4 Br1 117.4(3) . . ?
C4 C5 C6 120.3(3) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C7 C6 C5 120.5(3) . . ?
C7 C6 C8 123.2(3) . . ?
C5 C6 C8 116.4(3) . . ?
O2 C7 C6 124.9(3) . . ?
O2 C7 C2 118.0(3) . . ?
C6 C7 C2 117.1(3) . . ?
N1 C8 C6 127.6(3) . . ?
N1 C8 H8 116.2 . . ?
C6 C8 H8 116.2 . . ?
N1 C9 C10 111.5(3) . . ?
N1 C9 H9A 109.3 . . ?
C10 C9 H9A 109.3 . . ?
N1 C9 H9B 109.3 . . ?
C10 C9 H9B 109.3 . . ?
H9A C9 H9B 108.0 . . ?
C9 C10 S1 112.8(2) . . ?
C9 C10 H10A 109.0 . . ?
S1 C10 H10A 109.0 . . ?
C9 C10 H10B 109.0 . . ?
S1 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
N2 C11 C12 123.8(4) . . ?
N2 C11 H11 118.1 . . ?
C12 C11 H11 118.1 . . ?
C13 C12 C11 118.9(4) . . ?
C13 C12 H12 120.5 . . ?
C11 C12 H12 120.5 . . ?
C12 C13 C14 119.8(3) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C13 C14 C22 117.7(3) . . ?
C13 C14 C15 123.9(4) . . ?
C22 C14 C15 118.4(4) . . ?
C16 C15 C14 121.5(4) . . ?
C16 C15 H15 119.3 . . ?
C14 C15 H15 119.3 . . ?
C15 C16 C17 121.6(4) . . ?
C15 C16 H16 119.2 . . ?
C17 C16 H16 119.2 . . ?
C18 C17 C21 117.1(4) . . ?
C18 C17 C16 123.7(4) . . ?
C21 C17 C16 119.1(4) . . ?
C19 C18 C17 120.4(4) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C18 C19 C20 118.8(4) . . ?
C18 C19 H19 120.6 . . ?
C20 C19 H19 120.6 . . ?
N3 C20 C19 122.6(4) . . ?
N3 C20 H20 118.7 . . ?
C19 C20 H20 118.7 . . ?
N3 C21 C17 122.8(3) . . ?
N3 C21 C22 118.1(3) . . ?
C17 C21 C22 119.0(3) . . ?
N2 C22 C14 122.1(3) . . ?
N2 C22 C21 117.6(3) . . ?
C14 C22 C21 120.3(3) . . ?
O6 C23 C24 116.4(5) . . ?
O6 C23 H23A 108.2 . . ?
C24 C23 H23A 108.2 . . ?
O6 C23 H23B 108.2 . . ?
C24 C23 H23B 108.2 . . ?
H23A C23 H23B 107.3 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 Co1 O2 C7 -25.0(2) . . . . ?
O3 Co1 O2 C7 -139.5(18) . . . . ?
O1W Co1 O2 C7 -121.5(2) . . . . ?
N3 Co1 O2 C7 147.0(2) . . . . ?
N2 Co1 O2 C7 69.5(2) . . . . ?
O4 S1 O3 Co1 116.4(2) . . . . ?
O5 S1 O3 Co1 -115.2(2) . . . . ?
C10 S1 O3 Co1 -0.5(2) . . . . ?
O2 Co1 O3 S1 131.7(18) . . . . ?
N1 Co1 O3 S1 17.2(2) . . . . ?
O1W Co1 O3 S1 113.6(2) . . . . ?
N3 Co1 O3 S1 -154.7(2) . . . . ?
N2 Co1 O3 S1 -77.3(2) . . . . ?
O2 Co1 N1 C8 14.3(3) . . . . ?
O3 Co1 N1 C8 -168.2(3) . . . . ?
O1W Co1 N1 C8 105.9(3) . . . . ?
N3 Co1 N1 C8 -96.6(7) . . . . ?
N2 Co1 N1 C8 -80.5(3) . . . . ?
O2 Co1 N1 C9 -166.4(2) . . . . ?
O3 Co1 N1 C9 11.1(2) . . . . ?
O1W Co1 N1 C9 -74.8(2) . . . . ?
N3 Co1 N1 C9 82.7(7) . . . . ?
N2 Co1 N1 C9 98.8(2) . . . . ?
O2 Co1 N2 C11 -82.5(3) . . . . ?
N1 Co1 N2 C11 7.5(3) . . . . ?
O3 Co1 N2 C11 98.8(3) . . . . ?
O1W Co1 N2 C11 157.2(4) . . . . ?
N3 Co1 N2 C11 -174.9(3) . . . . ?
O2 Co1 N2 C22 102.5(2) . . . . ?
N1 Co1 N2 C22 -167.4(2) . . . . ?
O3 Co1 N2 C22 -76.1(2) . . . . ?
O1W Co1 N2 C22 -17.7(5) . . . . ?
N3 Co1 N2 C22 10.2(2) . . . . ?
O2 Co1 N3 C20 81.5(3) . . . . ?
N1 Co1 N3 C20 -167.8(6) . . . . ?
O3 Co1 N3 C20 -95.8(3) . . . . ?
O1W Co1 N3 C20 -10.2(3) . . . . ?
N2 Co1 N3 C20 175.8(3) . . . . ?
O2 Co1 N3 C21 -104.0(2) . . . . ?
N1 Co1 N3 C21 6.6(8) . . . . ?
O3 Co1 N3 C21 78.6(2) . . . . ?
O1W Co1 N3 C21 164.2(2) . . . . ?
N2 Co1 N3 C21 -9.8(2) . . . . ?
C1 O1 C2 C3 -8.6(5) . . . . ?
C1 O1 C2 C7 171.2(3) . . . . ?
O1 C2 C3 C4 -179.8(3) . . . . ?
C7 C2 C3 C4 0.4(5) . . . . ?
C2 C3 C4 C5 -0.1(6) . . . . ?
C2 C3 C4 Br1 -178.6(3) . . . . ?
C3 C4 C5 C6 -0.4(6) . . . . ?
Br1 C4 C5 C6 178.0(3) . . . . ?
C4 C5 C6 C7 0.7(5) . . . . ?
C4 C5 C6 C8 179.3(3) . . . . ?
Co1 O2 C7 C6 21.9(4) . . . . ?
Co1 O2 C7 C2 -158.8(2) . . . . ?
C5 C6 C7 O2 178.9(3) . . . . ?
C8 C6 C7 O2 0.3(5) . . . . ?
C5 C6 C7 C2 -0.4(4) . . . . ?
C8 C6 C7 C2 -178.9(3) . . . . ?
O1 C2 C7 O2 0.7(4) . . . . ?
C3 C2 C7 O2 -179.5(3) . . . . ?
O1 C2 C7 C6 -180.0(3) . . . . ?
C3 C2 C7 C6 -0.1(4) . . . . ?
C9 N1 C8 C6 -179.4(3) . . . . ?
Co1 N1 C8 C6 -0.1(5) . . . . ?
C7 C6 C8 N1 -11.9(5) . . . . ?
C5 C6 C8 N1 169.5(3) . . . . ?
C8 N1 C9 C10 122.4(3) . . . . ?
Co1 N1 C9 C10 -56.9(3) . . . . ?
N1 C9 C10 S1 81.8(3) . . . . ?
O4 S1 C10 C9 -168.8(2) . . . . ?
O5 S1 C10 C9 69.2(3) . . . . ?
O3 S1 C10 C9 -48.7(3) . . . . ?
C22 N2 C11 C12 0.9(5) . . . . ?
Co1 N2 C11 C12 -173.8(3) . . . . ?
N2 C11 C12 C13 0.8(6) . . . . ?
C11 C12 C13 C14 -1.4(6) . . . . ?
C12 C13 C14 C22 0.3(6) . . . . ?
C12 C13 C14 C15 -177.7(4) . . . . ?
C13 C14 C15 C16 175.4(4) . . . . ?
C22 C14 C15 C16 -2.6(6) . . . . ?
C14 C15 C16 C17 -0.1(7) . . . . ?
C15 C16 C17 C18 -176.6(4) . . . . ?
C15 C16 C17 C21 3.1(6) . . . . ?
C21 C17 C18 C19 -0.4(6) . . . . ?
C16 C17 C18 C19 179.3(4) . . . . ?
C17 C18 C19 C20 1.6(6) . . . . ?
C21 N3 C20 C19 0.4(5) . . . . ?
Co1 N3 C20 C19 174.6(3) . . . . ?
C18 C19 C20 N3 -1.7(6) . . . . ?
C20 N3 C21 C17 0.9(5) . . . . ?
Co1 N3 C21 C17 -174.1(3) . . . . ?
C20 N3 C21 C22 -176.6(3) . . . . ?
Co1 N3 C21 C22 8.3(3) . . . . ?
C18 C17 C21 N3 -0.9(5) . . . . ?
C16 C17 C21 N3 179.4(3) . . . . ?
C18 C17 C21 C22 176.6(3) . . . . ?
C16 C17 C21 C22 -3.1(5) . . . . ?
C11 N2 C22 C14 -2.0(4) . . . . ?
Co1 N2 C22 C14 173.6(2) . . . . ?
C11 N2 C22 C21 175.1(3) . . . . ?
Co1 N2 C22 C21 -9.3(3) . . . . ?
C13 C14 C22 N2 1.4(5) . . . . ?
C15 C14 C22 N2 179.6(3) . . . . ?
C13 C14 C22 C21 -175.6(3) . . . . ?
C15 C14 C22 C21 2.5(5) . . . . ?
N3 C21 C22 N2 0.8(4) . . . . ?
C17 C21 C22 N2 -176.9(3) . . . . ?
N3 C21 C22 C14 178.0(3) . . . . ?
C17 C21 C22 C14 0.3(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
O1W H1WA O2 0.848(9) 1.907(11) 2.741(3) 168(3) 2_657
O1W H1WB O6 0.846(9) 1.950(12) 2.783(3) 168(3) 8
O6 H6 O5 0.82 2.00 2.813(4) 171.7 8_554
O6 H6 S1 0.82 2.84 3.533(3) 143.5 8_554

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         1.255
_refine_diff_density_min         -0.715
_refine_diff_density_rms         0.067
####################################################################### 
# 
# 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_QINXYCu-1(CIF)
_database_code_depnum_ccdc_archive 'CCDC 1566125'
_audit_update_record             
;
2017-08-02 deposited with the CCDC.	2019-11-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H18 Br Cu N3 O5 S, C H4 O'
_chemical_formula_sum            'C23 H22 Br Cu N3 O6 S'
_chemical_formula_weight         611.95

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'
Br Br -0.2901 2.4595 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'

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

_cell_length_a                   15.516(8)
_cell_length_b                   13.3471(7)
_cell_length_c                   11.7999(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.625(19)
_cell_angle_gamma                90.00
_cell_volume                     2401.8(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2212
_cell_measurement_theta_min      3.6390
_cell_measurement_theta_max      23.0020

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.692
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1236
_exptl_absorpt_coefficient_mu    2.705
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.621
_exptl_absorpt_correction_T_max  0.805
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 15.9784
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12394
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_sigmaI/netI    0.0669
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.29
_diffrn_reflns_theta_max         26.37
_reflns_number_total             4912
_reflns_number_gt                3142
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0785P)²+3.1072P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4912
_refine_ls_number_parameters     319
_refine_ls_number_restraints     912
_refine_ls_R_factor_all          0.1061
_refine_ls_R_factor_gt           0.0647
_refine_ls_wR_factor_ref         0.1820
_refine_ls_wR_factor_gt          0.1543
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.012
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.53553(5) 0.28276(6) 1.09426(9) 0.0935(3) Uani 1 1 d U . .
Cu1 Cu 0.17240(4) 0.63322(5) 0.96170(5) 0.0407(2) Uani 1 1 d U . .
S1 S 0.22193(11) 0.87828(11) 0.97076(12) 0.0511(4) Uani 1 1 d U . .
O1 O 0.2971(3) 0.4213(4) 0.7515(4) 0.0778(14) Uani 1 1 d U . .
O2 O 0.2444(3) 0.5569(3) 0.8783(3) 0.0549(10) Uani 1 1 d U . .
O3 O 0.1872(4) 0.7900(4) 0.9102(4) 0.0953(16) Uani 1 1 d U . .
O4 O 0.2664(4) 0.9373(5) 0.8999(5) 0.116(2) Uani 1 1 d U . .
O5 O 0.1592(5) 0.9360(6) 1.0122(4) 0.125(3) Uani 1 1 d U . .
N1 N 0.2683(3) 0.6567(3) 1.0893(4) 0.0444(10) Uani 1 1 d U . .
N2 N 0.0710(3) 0.6346(3) 1.0561(4) 0.0429(10) Uani 1 1 d U . .
N3 N 0.0697(3) 0.6166(3) 0.8334(4) 0.0418(10) Uani 1 1 d U . .
C1 C 0.3319(6) 0.3572(7) 0.6743(7) 0.101(3) Uani 1 1 d U . .
H1A H 0.3902 0.3783 0.6696 0.152 Uiso 1 1 calc R . .
H1B H 0.2954 0.3607 0.5992 0.152 Uiso 1 1 calc R . .
H1C H 0.3333 0.2896 0.7022 0.152 Uiso 1 1 calc R . .
C2 C 0.3406(4) 0.4257(5) 0.8638(6) 0.0565(14) Uani 1 1 d U . .
C3 C 0.4063(4) 0.3613(5) 0.9137(6) 0.0654(16) Uani 1 1 d U . .
H3 H 0.4246 0.3100 0.8704 0.079 Uiso 1 1 calc R . .
C4 C 0.4445(4) 0.3732(5) 1.0278(6) 0.0606(16) Uani 1 1 d U . .
C5 C 0.4221(4) 0.4492(5) 1.0918(6) 0.0566(15) Uani 1 1 d U . .
H5 H 0.4517 0.4583 1.1671 0.068 Uiso 1 1 calc R . .
C6 C 0.3539(4) 0.5149(4) 1.0443(5) 0.0489(13) Uani 1 1 d U . .
C7 C 0.3100(4) 0.5024(4) 0.9285(5) 0.0494(13) Uani 1 1 d U . .
C8 C 0.3355(4) 0.5984(5) 1.1124(5) 0.0505(13) Uani 1 1 d U . .
H8 H 0.3758 0.6117 1.1794 0.061 Uiso 1 1 calc R . .
C9 C 0.2682(4) 0.7498(4) 1.1574(5) 0.0518(14) Uani 1 1 d U . .
H9A H 0.3067 0.7416 1.2315 0.062 Uiso 1 1 calc R . .
H9B H 0.2095 0.7625 1.1712 0.062 Uiso 1 1 calc R . .
C10 C 0.2989(4) 0.8390(4) 1.0947(5) 0.0533(14) Uani 1 1 d U . .
H10A H 0.3536 0.8217 1.0709 0.064 Uiso 1 1 calc R . .
H10B H 0.3105 0.8948 1.1480 0.064 Uiso 1 1 calc R . .
C11 C 0.0742(4) 0.6343(4) 1.1714(5) 0.0483(13) Uani 1 1 d U . .
H11 H 0.1286 0.6328 1.2201 0.058 Uiso 1 1 calc R . .
C12 C -0.0007(5) 0.6361(4) 1.2196(5) 0.0542(14) Uani 1 1 d U . .
H12 H 0.0036 0.6360 1.2993 0.065 Uiso 1 1 calc R . .
C13 C -0.0802(4) 0.6381(4) 1.1493(6) 0.0554(14) Uani 1 1 d U . .
H13 H -0.1307 0.6405 1.1813 0.067 Uiso 1 1 calc R . .
C14 C -0.0877(4) 0.6365(4) 1.0294(5) 0.0502(13) Uani 1 1 d U . .
C15 C -0.1675(4) 0.6357(5) 0.9483(6) 0.0612(15) Uani 1 1 d U . .
H15 H -0.2201 0.6419 0.9748 0.073 Uiso 1 1 calc R . .
C16 C -0.1697(4) 0.6264(5) 0.8344(6) 0.0641(16) Uani 1 1 d U . .
H16 H -0.2235 0.6243 0.7845 0.077 Uiso 1 1 calc R . .
C17 C -0.0891(4) 0.6193(4) 0.7875(5) 0.0494(13) Uani 1 1 d U . .
C18 C -0.0850(5) 0.6051(5) 0.6713(5) 0.0588(15) Uani 1 1 d U . .
H18 H -0.1363 0.6014 0.6166 0.071 Uiso 1 1 calc R . .
C19 C -0.0059(5) 0.5966(4) 0.6383(5) 0.0564(15) Uani 1 1 d U . .
H19 H -0.0028 0.5875 0.5610 0.068 Uiso 1 1 calc R . .
C20 C 0.0714(4) 0.6016(4) 0.7225(5) 0.0481(13) Uani 1 1 d U . .
H20 H 0.1253 0.5941 0.6997 0.058 Uiso 1 1 calc R . .
C21 C -0.0090(4) 0.6249(4) 0.8660(5) 0.0417(11) Uani 1 1 d U . .
C22 C -0.0081(4) 0.6335(4) 0.9869(5) 0.0391(11) Uani 1 1 d U . .
C23 C 0.3989(18) 0.4119(13) 0.3817(17) 0.265(10) Uani 1 1 d U . .
H23A H 0.4258 0.3701 0.4445 0.398 Uiso 1 1 calc R . .
H23B H 0.4071 0.3827 0.3102 0.398 Uiso 1 1 calc R . .
H23C H 0.3373 0.4176 0.3823 0.398 Uiso 1 1 calc R . .
O6 O 0.4360(16) 0.5038(17) 0.3933(18) 0.348(9) Uani 1 1 d U . .
H6 H 0.4511 0.5198 0.3327 0.521 Uiso 1 1 calc R . .


_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
Br1 C4 1.913(6) . ?
Cu1 O2 1.913(4) . ?
Cu1 N1 1.937(5) . ?
Cu1 N3 1.997(5) . ?
Cu1 N2 2.088(4) . ?
Cu1 O3 2.202(5) . ?
S1 O5 1.398(5) . ?
S1 O4 1.417(5) . ?
S1 O3 1.431(5) . ?
S1 C10 1.787(6) . ?
O1 C2 1.373(8) . ?
O1 C1 1.426(8) . ?
O2 C7 1.301(7) . ?
N1 C8 1.291(7) . ?
N1 C9 1.480(7) . ?
N2 C22 1.344(7) . ?
N2 C11 1.353(7) . ?
N3 C20 1.329(7) . ?
N3 C21 1.351(7) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.380(9) . ?
C2 C7 1.411(8) . ?
C3 C4 1.376(9) . ?
C3 H3 0.9300 . ?
C4 C5 1.348(9) . ?
C5 C6 1.408(8) . ?
C5 H5 0.9300 . ?
C6 C7 1.420(8) . ?
C6 C8 1.432(8) . ?
C8 H8 0.9300 . ?
C9 C10 1.524(8) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.384(8) . ?
C11 H11 0.9300 . ?
C12 C13 1.355(9) . ?
C12 H12 0.9300 . ?
C13 C14 1.398(8) . ?
C13 H13 0.9300 . ?
C14 C22 1.417(7) . ?
C14 C15 1.419(9) . ?
C15 C16 1.343(9) . ?
C15 H15 0.9300 . ?
C16 C17 1.460(9) . ?
C16 H16 0.9300 . ?
C17 C18 1.397(8) . ?
C17 C21 1.408(8) . ?
C18 C19 1.359(9) . ?
C18 H18 0.9300 . ?
C19 C20 1.411(8) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 C22 1.429(7) . ?
C23 O6 1.35(2) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
O6 H6 0.8200 . ?

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 N1 92.78(18) . . ?
O2 Cu1 N3 90.63(18) . . ?
N1 Cu1 N3 176.34(18) . . ?
O2 Cu1 N2 147.98(18) . . ?
N1 Cu1 N2 97.45(18) . . ?
N3 Cu1 N2 80.29(18) . . ?
O2 Cu1 O3 105.3(2) . . ?
N1 Cu1 O3 87.51(19) . . ?
N3 Cu1 O3 90.32(18) . . ?
N2 Cu1 O3 105.4(2) . . ?
O5 S1 O4 110.2(4) . . ?
O5 S1 O3 113.9(5) . . ?
O4 S1 O3 110.0(4) . . ?
O5 S1 C10 106.2(3) . . ?
O4 S1 C10 108.7(3) . . ?
O3 S1 C10 107.5(3) . . ?
C2 O1 C1 117.8(6) . . ?
C7 O2 Cu1 123.1(3) . . ?
S1 O3 Cu1 133.9(3) . . ?
C8 N1 C9 118.3(5) . . ?
C8 N1 Cu1 122.8(4) . . ?
C9 N1 Cu1 118.7(4) . . ?
C22 N2 C11 118.1(5) . . ?
C22 N2 Cu1 111.7(3) . . ?
C11 N2 Cu1 130.2(4) . . ?
C20 N3 C21 118.4(5) . . ?
C20 N3 Cu1 127.2(4) . . ?
C21 N3 Cu1 114.4(3) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 125.3(6) . . ?
O1 C2 C7 113.5(5) . . ?
C3 C2 C7 121.1(6) . . ?
C4 C3 C2 119.8(6) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C5 C4 C3 121.7(6) . . ?
C5 C4 Br1 119.5(5) . . ?
C3 C4 Br1 118.7(5) . . ?
C4 C5 C6 119.9(6) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C5 C6 C7 120.1(6) . . ?
C5 C6 C8 118.3(5) . . ?
C7 C6 C8 121.4(5) . . ?
O2 C7 C2 118.2(5) . . ?
O2 C7 C6 124.7(5) . . ?
C2 C7 C6 117.1(6) . . ?
N1 C8 C6 126.0(5) . . ?
N1 C8 H8 117.0 . . ?
C6 C8 H8 117.0 . . ?
N1 C9 C10 111.2(5) . . ?
N1 C9 H9A 109.4 . . ?
C10 C9 H9A 109.4 . . ?
N1 C9 H9B 109.4 . . ?
C10 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C9 C10 S1 113.9(4) . . ?
C9 C10 H10A 108.8 . . ?
S1 C10 H10A 108.8 . . ?
C9 C10 H10B 108.8 . . ?
S1 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
N2 C11 C12 122.4(6) . . ?
N2 C11 H11 118.8 . . ?
C12 C11 H11 118.8 . . ?
C13 C12 C11 119.2(6) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C12 C13 C14 121.0(6) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
C13 C14 C22 116.4(6) . . ?
C13 C14 C15 125.6(6) . . ?
C22 C14 C15 118.0(5) . . ?
C16 C15 C14 122.2(6) . . ?
C16 C15 H15 118.9 . . ?
C14 C15 H15 118.9 . . ?
C15 C16 C17 121.3(6) . . ?
C15 C16 H16 119.3 . . ?
C17 C16 H16 119.3 . . ?
C18 C17 C21 117.2(6) . . ?
C18 C17 C16 125.3(6) . . ?
C21 C17 C16 117.4(5) . . ?
C19 C18 C17 120.0(6) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C20 119.2(6) . . ?
C18 C19 H19 120.4 . . ?
C20 C19 H19 120.4 . . ?
N3 C20 C19 122.2(6) . . ?
N3 C20 H20 118.9 . . ?
C19 C20 H20 118.9 . . ?
N3 C21 C17 122.9(5) . . ?
N3 C21 C22 116.5(5) . . ?
C17 C21 C22 120.4(5) . . ?
N2 C22 C14 122.9(5) . . ?
N2 C22 C21 116.6(5) . . ?
C14 C22 C21 120.5(5) . . ?
O6 C23 H23A 109.5 . . ?
O6 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O6 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C23 O6 H6 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 Cu1 O2 C7 31.5(5) . . . . ?
N3 Cu1 O2 C7 -149.8(4) . . . . ?
N2 Cu1 O2 C7 -77.3(6) . . . . ?
O3 Cu1 O2 C7 119.7(4) . . . . ?
O5 S1 O3 Cu1 -92.7(6) . . . . ?
O4 S1 O3 Cu1 142.9(5) . . . . ?
C10 S1 O3 Cu1 24.6(6) . . . . ?
O2 Cu1 O3 S1 -116.5(5) . . . . ?
N1 Cu1 O3 S1 -24.3(6) . . . . ?
N3 Cu1 O3 S1 152.7(6) . . . . ?
N2 Cu1 O3 S1 72.7(6) . . . . ?
O2 Cu1 N1 C8 -24.3(5) . . . . ?
N3 Cu1 N1 C8 177(3) . . . . ?
N2 Cu1 N1 C8 125.3(4) . . . . ?
O3 Cu1 N1 C8 -129.5(5) . . . . ?
O2 Cu1 N1 C9 150.5(4) . . . . ?
N3 Cu1 N1 C9 -8(3) . . . . ?
N2 Cu1 N1 C9 -59.9(4) . . . . ?
O3 Cu1 N1 C9 45.3(4) . . . . ?
O2 Cu1 N2 C22 -81.0(5) . . . . ?
N1 Cu1 N2 C22 171.4(4) . . . . ?
N3 Cu1 N2 C22 -5.7(3) . . . . ?
O3 Cu1 N2 C22 82.0(4) . . . . ?
O2 Cu1 N2 C11 97.4(5) . . . . ?
N1 Cu1 N2 C11 -10.2(5) . . . . ?
N3 Cu1 N2 C11 172.8(5) . . . . ?
O3 Cu1 N2 C11 -99.6(5) . . . . ?
O2 Cu1 N3 C20 -26.4(5) . . . . ?
N1 Cu1 N3 C20 132(3) . . . . ?
N2 Cu1 N3 C20 -175.5(5) . . . . ?
O3 Cu1 N3 C20 78.9(5) . . . . ?
O2 Cu1 N3 C21 155.6(4) . . . . ?
N1 Cu1 N3 C21 -46(3) . . . . ?
N2 Cu1 N3 C21 6.5(4) . . . . ?
O3 Cu1 N3 C21 -99.1(4) . . . . ?
C1 O1 C2 C3 -11.6(10) . . . . ?
C1 O1 C2 C7 170.3(6) . . . . ?
O1 C2 C3 C4 -179.6(6) . . . . ?
C7 C2 C3 C4 -1.7(10) . . . . ?
C2 C3 C4 C5 -2.8(10) . . . . ?
C2 C3 C4 Br1 -179.9(5) . . . . ?
C3 C4 C5 C6 4.3(9) . . . . ?
Br1 C4 C5 C6 -178.7(4) . . . . ?
C4 C5 C6 C7 -1.2(9) . . . . ?
C4 C5 C6 C8 -176.3(6) . . . . ?
Cu1 O2 C7 C2 159.9(4) . . . . ?
Cu1 O2 C7 C6 -20.6(8) . . . . ?
O1 C2 C7 O2 2.2(8) . . . . ?
C3 C2 C7 O2 -176.0(6) . . . . ?
O1 C2 C7 C6 -177.4(5) . . . . ?
C3 C2 C7 C6 4.5(9) . . . . ?
C5 C6 C7 O2 177.5(5) . . . . ?
C8 C6 C7 O2 -7.6(9) . . . . ?
C5 C6 C7 C2 -3.0(8) . . . . ?
C8 C6 C7 C2 171.9(5) . . . . ?
C9 N1 C8 C6 -168.9(5) . . . . ?
Cu1 N1 C8 C6 5.9(8) . . . . ?
C5 C6 C8 N1 -169.4(6) . . . . ?
C7 C6 C8 N1 15.6(9) . . . . ?
C8 N1 C9 C10 96.3(6) . . . . ?
Cu1 N1 C9 C10 -78.6(5) . . . . ?
N1 C9 C10 S1 71.0(6) . . . . ?
O5 S1 C10 C9 80.0(6) . . . . ?
O4 S1 C10 C9 -161.4(5) . . . . ?
O3 S1 C10 C9 -42.3(5) . . . . ?
C22 N2 C11 C12 -2.1(8) . . . . ?
Cu1 N2 C11 C12 179.5(4) . . . . ?
N2 C11 C12 C13 0.2(8) . . . . ?
C11 C12 C13 C14 1.1(9) . . . . ?
C12 C13 C14 C22 -0.5(8) . . . . ?
C12 C13 C14 C15 178.3(6) . . . . ?
C13 C14 C15 C16 -174.7(6) . . . . ?
C22 C14 C15 C16 4.0(9) . . . . ?
C14 C15 C16 C17 -1.8(10) . . . . ?
C15 C16 C17 C18 177.0(6) . . . . ?
C15 C16 C17 C21 -1.3(9) . . . . ?
C21 C17 C18 C19 0.4(9) . . . . ?
C16 C17 C18 C19 -177.9(6) . . . . ?
C17 C18 C19 C20 0.5(9) . . . . ?
C21 N3 C20 C19 1.6(8) . . . . ?
Cu1 N3 C20 C19 -176.3(4) . . . . ?
C18 C19 C20 N3 -1.5(9) . . . . ?
C20 N3 C21 C17 -0.7(8) . . . . ?
Cu1 N3 C21 C17 177.5(4) . . . . ?
C20 N3 C21 C22 175.5(5) . . . . ?
Cu1 N3 C21 C22 -6.3(6) . . . . ?
C18 C17 C21 N3 -0.3(8) . . . . ?
C16 C17 C21 N3 178.2(5) . . . . ?
C18 C17 C21 C22 -176.3(5) . . . . ?
C16 C17 C21 C22 2.1(8) . . . . ?
C11 N2 C22 C14 2.9(8) . . . . ?
Cu1 N2 C22 C14 -178.5(4) . . . . ?
C11 N2 C22 C21 -174.6(4) . . . . ?
Cu1 N2 C22 C21 4.1(6) . . . . ?
C13 C14 C22 N2 -1.6(8) . . . . ?
C15 C14 C22 N2 179.5(5) . . . . ?
C13 C14 C22 C21 175.7(5) . . . . ?
C15 C14 C22 C21 -3.1(8) . . . . ?
N3 C21 C22 N2 1.3(7) . . . . ?
C17 C21 C22 N2 177.6(5) . . . . ?
N3 C21 C22 C14 -176.2(5) . . . . ?
C17 C21 C22 C14 0.1(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         1.645
_refine_diff_density_min         -0.661
_refine_diff_density_rms         0.092
