# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_exp_1691
_database_code_depnum_ccdc_archive 'CCDC 1586105'
_audit_update_record             
;
2017-11-17 deposited with the CCDC.
2018-06-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H20 Br2 Cu N8 S'
_chemical_formula_weight         639.87

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'
Br Br -0.6763 1.2805 '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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P n a 21'

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

_cell_length_a                   8.6476(3)
_cell_length_b                   15.2470(4)
_cell_length_c                   20.5679(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2711.89(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.01(10)
_cell_measurement_reflns_used    3088
_cell_measurement_theta_min      5.7920
_cell_measurement_theta_max      70.5790

_exptl_crystal_description       needle
_exptl_crystal_colour            'clear light green'
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.040
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.567
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1268
_exptl_absorpt_coefficient_mu    5.505
_exptl_absorpt_correction_T_min  0.66415
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.642
_oxdiff_exptl_absorpt_empirical_full_max 1.425
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;


_diffrn_ambient_temperature      100.01(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.0793
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         7283
_diffrn_standards_interval_count 1.00
_diffrn_standards_interval_time  1.00
_diffrn_standards_decay_%        none
_diffrn_reflns_number            6550
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_av_sigmaI/netI    0.0333
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.61
_diffrn_reflns_theta_max         67.08
_reflns_number_total             3708
_reflns_number_gt                3525
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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)+(0.0797P)²+4.4488P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00
_refine_ls_number_reflns         3708
_refine_ls_number_parameters     329
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0442
_refine_ls_wR_factor_ref         0.1294
_refine_ls_wR_factor_gt          0.1269
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.082
_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 0.92446(11) 0.51655(5) 0.40967(5) 0.0452(3) Uani 1 1 d . . .
Br2 Br 0.50186(9) 0.48577(4) 0.56368(5) 0.0310(2) Uani 1 1 d . . .
C1 C 0.6417(8) 0.6942(5) 0.4548(3) 0.0239(14) Uani 1 1 d . . .
H1 H 0.5750 0.6764 0.4219 0.029 Uiso 1 1 calc R . .
C2 C 0.6667(8) 0.7847(5) 0.4627(4) 0.0270(15) Uani 1 1 d . . .
H2 H 0.6175 0.8252 0.4360 0.032 Uiso 1 1 calc R . .
C3 C 0.7648(7) 0.8114(4) 0.5106(3) 0.0219(14) Uani 1 1 d . . .
H3 H 0.7832 0.8709 0.5171 0.026 Uiso 1 1 calc R . .
C4 C 0.8384(7) 0.7484(4) 0.5503(3) 0.0217(14) Uani 1 1 d . . .
C5 C 0.8075(7) 0.6583(4) 0.5391(3) 0.0200(13) Uani 1 1 d . . .
C6 C 0.8780(8) 0.5944(4) 0.5789(3) 0.0263(15) Uani 1 1 d . . .
H6 H 0.8542 0.5355 0.5728 0.032 Uiso 1 1 calc R . .
C7 C 0.9798(8) 0.6179(4) 0.6257(3) 0.0228(14) Uani 1 1 d . . .
H7 H 1.0267 0.5747 0.6508 0.027 Uiso 1 1 calc R . .
C8 C 1.0165(7) 0.7080(4) 0.6372(3) 0.0199(14) Uani 1 1 d . . .
C9 C 0.9436(8) 0.7720(5) 0.5994(3) 0.0225(14) Uani 1 1 d . . .
H9 H 0.9650 0.8309 0.6068 0.027 Uiso 1 1 calc R . .
C10 C 1.1308(8) 0.7268(4) 0.6880(3) 0.0199(13) Uani 1 1 d . . .
C11 C 1.2830(8) 0.7899(5) 0.7578(3) 0.0233(15) Uani 1 1 d . . .
C12 C 1.4817(8) 0.8028(5) 0.8570(4) 0.0240(15) Uani 1 1 d . . .
H12A H 1.5320 0.7583 0.8308 0.029 Uiso 1 1 calc R . .
H12B H 1.5619 0.8381 0.8770 0.029 Uiso 1 1 calc R . .
C13 C 1.3897(7) 0.7584(4) 0.9097(3) 0.0210(13) Uani 1 1 d . . .
C14 C 1.3888(7) 0.6676(4) 0.9149(3) 0.0198(13) Uani 1 1 d . . .
H14 H 1.4425 0.6352 0.8840 0.024 Uiso 1 1 calc R . .
C15 C 1.2316(9) 0.6708(5) 1.0046(4) 0.0311(17) Uani 1 1 d . . .
H15 H 1.1762 0.6407 1.0363 0.037 Uiso 1 1 calc R . .
C16 C 1.2248(9) 0.7613(5) 1.0035(4) 0.0290(16) Uani 1 1 d . . .
H16 H 1.1670 0.7917 1.0342 0.035 Uiso 1 1 calc R . .
C17 C 1.3059(8) 0.8060(5) 0.9555(3) 0.0271(15) Uani 1 1 d . . .
H17 H 1.3043 0.8670 0.9540 0.032 Uiso 1 1 calc R . .
C18 C 0.3980(9) 0.5474(6) 0.3594(5) 0.042(2) Uani 1 1 d . . .
C19 C 0.2846(12) 0.5834(7) 0.3108(6) 0.060(3) Uani 1 1 d . . .
H19A H 0.2963 0.6459 0.3079 0.090 Uiso 1 1 calc R . .
H19B H 0.1812 0.5696 0.3244 0.090 Uiso 1 1 calc R . .
H19C H 0.3038 0.5576 0.2690 0.090 Uiso 1 1 calc R . .
C20 C 0.025(2) 0.3212(14) 0.6516(11) 0.071(8) Uani 0.50 1 d PD . .
C21 C 0.076(3) 0.2250(13) 0.6624(10) 0.059(5) Uani 0.50 1 d PD . .
H21A H 0.0986 0.2160 0.7076 0.088 Uiso 0.50 1 calc PR . .
H21B H 0.1660 0.2130 0.6369 0.088 Uiso 0.50 1 calc PR . .
H21C H -0.0064 0.1863 0.6495 0.088 Uiso 0.50 1 calc PR . .
C22 C 0.284(2) 0.3771(12) 0.7719(8) 0.047(5) Uani 0.50 1 d P . .
C23 C 0.257(2) 0.4712(11) 0.7512(8) 0.038(4) Uani 0.50 1 d PU . .
H23A H 0.3089 0.5100 0.7808 0.058 Uiso 0.50 1 calc PR . .
H23B H 0.1480 0.4835 0.7517 0.058 Uiso 0.50 1 calc PR . .
H23C H 0.2965 0.4798 0.7081 0.058 Uiso 0.50 1 calc PR . .
Cu1 Cu 0.67968(13) 0.50569(6) 0.47033(5) 0.0253(2) Uani 1 1 d . . .
N1 N 0.7058(7) 0.6334(4) 0.4906(3) 0.0262(13) Uani 1 1 d . . .
N2 N 1.3153(7) 0.6249(4) 0.9617(3) 0.0293(14) Uani 1 1 d . . .
N3 N 1.2197(7) 0.6663(4) 0.7134(3) 0.0231(12) Uani 1 1 d . . .
N4 N 1.3156(7) 0.7051(4) 0.7586(3) 0.0245(13) Uani 1 1 d . . .
N5 N 1.1705(6) 0.8072(4) 0.7148(3) 0.0188(11) Uani 1 1 d . . .
N6 N 1.1054(7) 0.8917(3) 0.7093(3) 0.0257(13) Uani 1 1 d . . .
H6A H 1.1252 0.9150 0.6715 0.031 Uiso 1 1 d R . .
H6B H 1.0051 0.8904 0.7142 0.031 Uiso 1 1 d R . .
N7 N 0.4975(12) 0.5275(5) 0.3912(4) 0.060(3) Uani 1 1 d . . .
N8 N 0.322(3) 0.3076(13) 0.7890(8) 0.085(8) Uani 0.50 1 d P . .
N9 N -0.021(2) 0.3829(9) 0.6438(10) 0.066(6) Uani 0.50 1 d P . .
S1 S 1.36630(19) 0.87198(10) 0.80457(9) 0.0235(3) 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
Br1 Cu1 2.4627(14) . ?
Br2 Cu1 2.4784(14) . ?
C1 N1 1.307(9) . ?
C1 C2 1.405(10) . ?
C1 H1 0.9300 . ?
C2 C3 1.362(10) . ?
C2 H2 0.9300 . ?
C3 C4 1.413(9) . ?
C3 H3 0.9300 . ?
C4 C9 1.405(10) . ?
C4 C5 1.417(9) . ?
C5 N1 1.383(9) . ?
C5 C6 1.411(10) . ?
C6 C7 1.353(10) . ?
C6 H6 0.9300 . ?
C7 C8 1.429(9) . ?
C7 H7 0.9300 . ?
C8 C9 1.398(10) . ?
C8 C10 1.467(10) . ?
C9 H9 0.9300 . ?
C10 N3 1.310(9) . ?
C10 N5 1.387(9) . ?
C11 N4 1.323(9) . ?
C11 N5 1.340(9) . ?
C11 S1 1.735(7) . ?
C12 C13 1.505(9) . ?
C12 S1 1.809(7) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.388(9) . ?
C13 C17 1.393(10) . ?
C14 N2 1.324(9) . ?
C14 H14 0.9300 . ?
C15 N2 1.340(10) . ?
C15 C16 1.381(11) . ?
C15 H15 0.9300 . ?
C16 C17 1.390(10) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 N7 1.122(12) . ?
C18 C19 1.505(14) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 N9 1.03(2) . ?
C20 C21 1.548(10) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 N8 1.17(3) . ?
C22 C23 1.52(2) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
Cu1 N2 2.000(6) 2_764 ?
Cu1 N1 2.004(6) . ?
Cu1 N7 2.290(9) . ?
N2 Cu1 2.000(6) 2_765 ?
N3 N4 1.380(8) . ?
N5 N6 1.411(7) . ?
N6 H6A 0.8728 . ?
N6 H6B 0.8736 . ?

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
N1 C1 C2 124.5(7) . . ?
N1 C1 H1 117.8 . . ?
C2 C1 H1 117.8 . . ?
C3 C2 C1 118.3(7) . . ?
C3 C2 H2 120.9 . . ?
C1 C2 H2 120.9 . . ?
C2 C3 C4 119.6(6) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C9 C4 C3 122.2(6) . . ?
C9 C4 C5 119.2(6) . . ?
C3 C4 C5 118.7(6) . . ?
N1 C5 C6 120.2(6) . . ?
N1 C5 C4 120.3(6) . . ?
C6 C5 C4 119.5(6) . . ?
C7 C6 C5 120.7(6) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C7 C8 121.1(6) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 H7 119.4 . . ?
C9 C8 C7 118.6(6) . . ?
C9 C8 C10 124.3(6) . . ?
C7 C8 C10 117.1(6) . . ?
C8 C9 C4 120.8(6) . . ?
C8 C9 H9 119.6 . . ?
C4 C9 H9 119.6 . . ?
N3 C10 N5 108.5(6) . . ?
N3 C10 C8 122.8(6) . . ?
N5 C10 C8 128.6(6) . . ?
N4 C11 N5 110.8(6) . . ?
N4 C11 S1 127.5(6) . . ?
N5 C11 S1 121.7(5) . . ?
C13 C12 S1 113.6(5) . . ?
C13 C12 H12A 108.9 . . ?
S1 C12 H12A 108.9 . . ?
C13 C12 H12B 108.9 . . ?
S1 C12 H12B 108.9 . . ?
H12A C12 H12B 107.7 . . ?
C14 C13 C17 117.7(6) . . ?
C14 C13 C12 120.5(6) . . ?
C17 C13 C12 121.8(6) . . ?
N2 C14 C13 123.3(6) . . ?
N2 C14 H14 118.4 . . ?
C13 C14 H14 118.4 . . ?
N2 C15 C16 122.2(7) . . ?
N2 C15 H15 118.9 . . ?
C16 C15 H15 118.9 . . ?
C15 C16 C17 118.8(7) . . ?
C15 C16 H16 120.6 . . ?
C17 C16 H16 120.6 . . ?
C16 C17 C13 119.1(6) . . ?
C16 C17 H17 120.4 . . ?
C13 C17 H17 120.4 . . ?
N7 C18 C19 170.3(11) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N9 C20 C21 174(2) . . ?
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 . . ?
N8 C22 C23 172(2) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N2 Cu1 N1 169.6(3) 2_764 . ?
N2 Cu1 N7 95.5(3) 2_764 . ?
N1 Cu1 N7 94.9(3) . . ?
N2 Cu1 Br1 90.19(18) 2_764 . ?
N1 Cu1 Br1 86.73(17) . . ?
N7 Cu1 Br1 102.8(3) . . ?
N2 Cu1 Br2 87.73(18) 2_764 . ?
N1 Cu1 Br2 91.60(17) . . ?
N7 Cu1 Br2 98.1(3) . . ?
Br1 Cu1 Br2 159.07(6) . . ?
C1 N1 C5 118.7(6) . . ?
C1 N1 Cu1 121.6(5) . . ?
C5 N1 Cu1 119.3(5) . . ?
C14 N2 C15 118.8(6) . . ?
C14 N2 Cu1 123.0(5) . 2_765 ?
C15 N2 Cu1 118.2(5) . 2_765 ?
C10 N3 N4 108.7(6) . . ?
C11 N4 N3 106.4(6) . . ?
C11 N5 C10 105.6(5) . . ?
C11 N5 N6 121.5(6) . . ?
C10 N5 N6 132.5(6) . . ?
N5 N6 H6A 111.5 . . ?
N5 N6 H6B 111.5 . . ?
H6A N6 H6B 107.9 . . ?
C18 N7 Cu1 168.7(8) . . ?
C11 S1 C12 98.0(3) . . ?

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 C1 C2 C3 0.3(11) . . . . ?
C1 C2 C3 C4 0.3(10) . . . . ?
C2 C3 C4 C9 178.4(6) . . . . ?
C2 C3 C4 C5 -0.1(10) . . . . ?
C9 C4 C5 N1 -179.2(6) . . . . ?
C3 C4 C5 N1 -0.7(9) . . . . ?
C9 C4 C5 C6 2.4(10) . . . . ?
C3 C4 C5 C6 -179.1(6) . . . . ?
N1 C5 C6 C7 178.7(6) . . . . ?
C4 C5 C6 C7 -2.9(10) . . . . ?
C5 C6 C7 C8 1.3(11) . . . . ?
C6 C7 C8 C9 0.6(10) . . . . ?
C6 C7 C8 C10 -178.7(6) . . . . ?
C7 C8 C9 C4 -1.0(10) . . . . ?
C10 C8 C9 C4 178.2(6) . . . . ?
C3 C4 C9 C8 -179.0(6) . . . . ?
C5 C4 C9 C8 -0.5(10) . . . . ?
C9 C8 C10 N3 -165.7(7) . . . . ?
C7 C8 C10 N3 13.5(9) . . . . ?
C9 C8 C10 N5 10.6(11) . . . . ?
C7 C8 C10 N5 -170.1(6) . . . . ?
S1 C12 C13 C14 122.3(6) . . . . ?
S1 C12 C13 C17 -59.2(8) . . . . ?
C17 C13 C14 N2 -1.4(10) . . . . ?
C12 C13 C14 N2 177.1(6) . . . . ?
N2 C15 C16 C17 0.9(12) . . . . ?
C15 C16 C17 C13 0.8(11) . . . . ?
C14 C13 C17 C16 -0.6(10) . . . . ?
C12 C13 C17 C16 -179.1(6) . . . . ?
C2 C1 N1 C5 -1.1(11) . . . . ?
C2 C1 N1 Cu1 -173.9(6) . . . . ?
C6 C5 N1 C1 179.6(6) . . . . ?
C4 C5 N1 C1 1.2(10) . . . . ?
C6 C5 N1 Cu1 -7.3(8) . . . . ?
C4 C5 N1 Cu1 174.3(5) . . . . ?
N2 Cu1 N1 C1 167.1(13) 2_764 . . . ?
N7 Cu1 N1 C1 -8.4(6) . . . . ?
Br1 Cu1 N1 C1 94.2(5) . . . . ?
Br2 Cu1 N1 C1 -106.7(5) . . . . ?
N2 Cu1 N1 C5 -5.7(18) 2_764 . . . ?
N7 Cu1 N1 C5 178.8(5) . . . . ?
Br1 Cu1 N1 C5 -78.7(5) . . . . ?
Br2 Cu1 N1 C5 80.4(5) . . . . ?
C13 C14 N2 C15 3.1(10) . . . . ?
C13 C14 N2 Cu1 -178.0(5) . . . 2_765 ?
C16 C15 N2 C14 -2.9(11) . . . . ?
C16 C15 N2 Cu1 178.2(6) . . . 2_765 ?
N5 C10 N3 N4 1.9(7) . . . . ?
C8 C10 N3 N4 178.9(6) . . . . ?
N5 C11 N4 N3 0.5(8) . . . . ?
S1 C11 N4 N3 179.8(5) . . . . ?
C10 N3 N4 C11 -1.5(7) . . . . ?
N4 C11 N5 C10 0.6(8) . . . . ?
S1 C11 N5 C10 -178.7(5) . . . . ?
N4 C11 N5 N6 174.1(6) . . . . ?
S1 C11 N5 N6 -5.3(9) . . . . ?
N3 C10 N5 C11 -1.6(7) . . . . ?
C8 C10 N5 C11 -178.3(7) . . . . ?
N3 C10 N5 N6 -174.0(6) . . . . ?
C8 C10 N5 N6 9.2(12) . . . . ?
C19 C18 N7 Cu1 103(7) . . . . ?
N2 Cu1 N7 C18 136(5) 2_764 . . . ?
N1 Cu1 N7 C18 -45(5) . . . . ?
Br1 Cu1 N7 C18 -132(5) . . . . ?
Br2 Cu1 N7 C18 48(5) . . . . ?
N4 C11 S1 C12 -7.0(7) . . . . ?
N5 C11 S1 C12 172.3(6) . . . . ?
C13 C12 S1 C11 -77.2(6) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        67.08
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.794
_refine_diff_density_min         -0.513
_refine_diff_density_rms         0.119
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_preparation       'Magnetic properties'
####################################################################### 
# 
# 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_exp_1609
_database_code_depnum_ccdc_archive 'CCDC 1586109'
_audit_update_record             
;
2017-11-17 deposited with the CCDC.
2018-06-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H24 Br2 Cu N7 O1.50 S'
_chemical_formula_weight         653.89

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'
Br Br -0.6763 1.2805 '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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P n a 21'

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

_cell_length_a                   8.7700(3)
_cell_length_b                   14.9616(4)
_cell_length_c                   20.7948(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2728.55(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.01(10)
_cell_measurement_reflns_used    3611
_cell_measurement_theta_min      5.1640
_cell_measurement_theta_max      70.7940

_exptl_crystal_description       needle
_exptl_crystal_colour            'clear light green'
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.050
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.592
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1304
_exptl_absorpt_coefficient_mu    5.514
_exptl_absorpt_correction_T_min  0.50251
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.627
_oxdiff_exptl_absorpt_empirical_full_max 1.598
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;


_diffrn_ambient_temperature      100.01(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.0793
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         6922
_diffrn_standards_interval_count 1.00
_diffrn_standards_interval_time  1.00
_diffrn_standards_decay_%        none
_diffrn_reflns_number            6415
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_av_sigmaI/netI    0.0303
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.64
_diffrn_reflns_theta_max         70.94
_reflns_number_total             3364
_reflns_number_gt                3257
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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)+(0.0976P)²+7.2316P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00
_refine_ls_number_reflns         3364
_refine_ls_number_parameters     318
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0552
_refine_ls_wR_factor_ref         0.1579
_refine_ls_wR_factor_gt          0.1563
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.096
_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 0.58987(17) 0.02120(7) 0.43780(6) 0.0607(4) Uani 1 1 d . . .
Br2 Br 0.99975(11) -0.02065(5) 0.28241(6) 0.0384(3) Uani 1 1 d . . .
C1 C 0.8754(11) 0.1949(6) 0.3851(5) 0.0350(19) Uani 1 1 d . . .
H1 H 0.9450 0.1772 0.4164 0.042 Uiso 1 1 calc R . .
C2 C 0.8513(10) 0.2863(5) 0.3751(5) 0.0333(18) Uani 1 1 d . . .
H2A H 0.9051 0.3282 0.3992 0.040 Uiso 1 1 calc R . .
C3 C 0.7511(10) 0.3134(5) 0.3309(4) 0.0292(17) Uani 1 1 d . . .
H3 H 0.7315 0.3740 0.3255 0.035 Uiso 1 1 calc R . .
C4 C 0.6745(9) 0.2492(5) 0.2920(4) 0.0293(17) Uani 1 1 d . . .
C5 C 0.7064(9) 0.1576(5) 0.3044(4) 0.0269(16) Uani 1 1 d . . .
C6 C 0.6287(10) 0.0922(5) 0.2663(4) 0.0290(17) Uani 1 1 d . . .
H6 H 0.6463 0.0318 0.2736 0.035 Uiso 1 1 calc R . .
C7 C 0.5311(10) 0.1171(5) 0.2203(4) 0.0306(18) Uani 1 1 d . . .
H7 H 0.4829 0.0734 0.1958 0.037 Uiso 1 1 calc R . .
C8 C 0.4989(9) 0.2090(5) 0.2077(4) 0.0256(16) Uani 1 1 d . . .
C9 C 0.5709(9) 0.2734(5) 0.2440(4) 0.0287(17) Uani 1 1 d . . .
H9 H 0.5504 0.3334 0.2365 0.034 Uiso 1 1 calc R . .
C10 C 0.3811(9) 0.2272(5) 0.1571(4) 0.0254(16) Uani 1 1 d . . .
C11 C 0.2304(10) 0.2933(5) 0.0890(4) 0.0280(17) Uani 1 1 d . . .
C12 C 0.0298(10) 0.3069(6) -0.0080(4) 0.0317(18) Uani 1 1 d . . .
H12A H -0.0184 0.2608 0.0177 0.038 Uiso 1 1 calc R . .
H12B H -0.0500 0.3431 -0.0271 0.038 Uiso 1 1 calc R . .
C13 C 0.1202(8) 0.2645(5) -0.0597(4) 0.0250(15) Uani 1 1 d . . .
C14 C 0.2052(9) 0.3125(5) -0.1041(4) 0.0298(17) Uani 1 1 d . . .
H14 H 0.2127 0.3743 -0.1005 0.036 Uiso 1 1 calc R . .
C15 C 0.2790(10) 0.2684(6) -0.1537(4) 0.0342(19) Uani 1 1 d . . .
H15 H 0.3356 0.3003 -0.1837 0.041 Uiso 1 1 calc R . .
C16 C 0.2678(10) 0.1781(6) -0.1580(4) 0.0318(18) Uani 1 1 d . . .
H16 H 0.3155 0.1489 -0.1920 0.038 Uiso 1 1 calc R . .
C17 C 0.1150(8) 0.1717(5) -0.0670(4) 0.0231(15) Uani 1 1 d . . .
H17 H 0.0582 0.1383 -0.0379 0.028 Uiso 1 1 calc R . .
C18 C 0.980(2) 0.0420(9) 0.5061(10) 0.079(5) Uani 1 1 d . . .
H18 H 0.8952 0.0180 0.5264 0.095 Uiso 1 1 calc R . .
C20 C 1.232(3) 0.1217(15) 0.5210(9) 0.136(10) Uani 1 1 d D . .
H20A H 1.2593 0.0871 0.4839 0.203 Uiso 1 1 calc R . .
H20B H 1.3052 0.1122 0.5545 0.203 Uiso 1 1 calc R . .
H20C H 1.2294 0.1839 0.5098 0.203 Uiso 1 1 calc R . .
C21 C 1.029(4) 0.1078(14) 0.6120(10) 0.163(12) Uani 1 1 d . . .
H21A H 0.9311 0.0807 0.6192 0.245 Uiso 1 1 calc R . .
H21B H 1.0222 0.1708 0.6203 0.245 Uiso 1 1 calc R . .
H21C H 1.1027 0.0815 0.6402 0.245 Uiso 1 1 calc R . .
C22 C 0.609(4) 0.0870(16) 0.6252(10) 0.083(10) Uani 0.50 1 d PD . .
H22A H 0.6959 0.0472 0.6242 0.100 Uiso 0.50 1 calc PR . .
H22B H 0.5166 0.0516 0.6204 0.100 Uiso 0.50 1 calc PR . .
C23 C 0.605(4) 0.1390(19) 0.6887(14) 0.085(10) Uani 0.50 1 d PD . .
H23A H 0.6726 0.1893 0.6859 0.127 Uiso 0.50 1 calc PR . .
H23B H 0.6368 0.1006 0.7232 0.127 Uiso 0.50 1 calc PR . .
H23C H 0.5031 0.1597 0.6968 0.127 Uiso 0.50 1 calc PR . .
Cu1 Cu 0.82606(15) 0.00289(8) 0.37423(7) 0.0316(3) Uani 1 1 d . . .
N1 N 0.8027(9) 0.1327(5) 0.3518(4) 0.0345(17) Uani 1 1 d . . .
N2 N 0.2952(8) 0.1659(5) 0.1324(3) 0.0296(14) Uani 1 1 d . . .
N3 N 0.1967(8) 0.2062(5) 0.0887(3) 0.0295(15) Uani 1 1 d . . .
N4 N 0.3456(9) 0.3094(5) 0.1315(3) 0.0317(16) Uani 1 1 d . . .
N5 N 0.4097(10) 0.3945(5) 0.1362(4) 0.0382(18) Uani 1 1 d . . .
H5A H 0.4049 0.4147 0.1760 0.046 Uiso 1 1 d R . .
H5B H 0.5068 0.3932 0.1255 0.046 Uiso 1 1 d R . .
N6 N 0.1890(8) 0.1292(5) -0.1142(3) 0.0304(15) Uani 1 1 d . . .
N7 N 1.075(2) 0.0931(8) 0.5443(7) 0.103(6) Uani 1 1 d D . .
O1 O 0.9935(13) 0.0252(5) 0.4518(5) 0.076(4) Uani 1 1 d . . .
O2 O 0.619(4) 0.1503(13) 0.5758(11) 0.101(8) Uani 0.50 1 d PD . .
H2 H 0.6214 0.1247 0.5410 0.151 Uiso 0.50 1 calc PR . .
S1 S 0.1491(3) 0.37770(14) 0.04433(11) 0.0360(5) 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
Br1 Cu1 2.4725(18) . ?
Br2 Cu1 2.4679(18) . ?
C1 N1 1.324(12) . ?
C1 C2 1.400(11) . ?
C1 H1 0.9300 . ?
C2 C3 1.335(13) . ?
C2 H2A 0.9300 . ?
C3 C4 1.424(11) . ?
C3 H3 0.9300 . ?
C4 C9 1.397(12) . ?
C4 C5 1.423(11) . ?
C5 N1 1.350(11) . ?
C5 C6 1.432(11) . ?
C6 C7 1.337(12) . ?
C6 H6 0.9300 . ?
C7 C8 1.428(10) . ?
C7 H7 0.9300 . ?
C8 C9 1.376(11) . ?
C8 C10 1.500(12) . ?
C9 H9 0.9300 . ?
C10 N2 1.294(11) . ?
C10 N4 1.376(10) . ?
C11 N3 1.337(10) . ?
C11 N4 1.364(11) . ?
C11 S1 1.722(9) . ?
C12 C13 1.478(11) . ?
C12 S1 1.844(10) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.387(12) . ?
C13 C17 1.397(10) . ?
C14 C15 1.385(12) . ?
C14 H14 0.9300 . ?
C15 C16 1.357(12) . ?
C15 H15 0.9300 . ?
C16 N6 1.357(11) . ?
C16 H16 0.9300 . ?
C17 N6 1.338(10) . ?
C17 H17 0.9300 . ?
C18 O1 1.16(2) . ?
C18 N7 1.38(2) . ?
C18 H18 0.9300 . ?
C20 N7 1.515(10) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 N7 1.48(3) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 O2 1.400(10) . ?
C22 C23 1.533(10) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
Cu1 N6 1.996(7) 2_655 ?
Cu1 N1 2.007(7) . ?
Cu1 O1 2.207(8) . ?
N2 N3 1.391(10) . ?
N4 N5 1.394(10) . ?
N5 H5A 0.8813 . ?
N5 H5B 0.8808 . ?
N6 Cu1 1.996(7) 2_654 ?
O2 H2 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
N1 C1 C2 122.5(9) . . ?
N1 C1 H1 118.8 . . ?
C2 C1 H1 118.8 . . ?
C3 C2 C1 119.9(8) . . ?
C3 C2 H2A 120.1 . . ?
C1 C2 H2A 120.1 . . ?
C2 C3 C4 119.8(7) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C9 C4 C5 120.5(7) . . ?
C9 C4 C3 122.6(7) . . ?
C5 C4 C3 116.9(8) . . ?
N1 C5 C4 121.5(8) . . ?
N1 C5 C6 120.9(7) . . ?
C4 C5 C6 117.6(7) . . ?
C7 C6 C5 120.7(7) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C7 C8 121.7(8) . . ?
C6 C7 H7 119.2 . . ?
C8 C7 H7 119.2 . . ?
C9 C8 C7 118.9(8) . . ?
C9 C8 C10 125.0(7) . . ?
C7 C8 C10 116.1(7) . . ?
C8 C9 C4 120.6(7) . . ?
C8 C9 H9 119.7 . . ?
C4 C9 H9 119.7 . . ?
N2 C10 N4 110.4(7) . . ?
N2 C10 C8 123.4(7) . . ?
N4 C10 C8 126.1(7) . . ?
N3 C11 N4 109.8(7) . . ?
N3 C11 S1 128.4(7) . . ?
N4 C11 S1 121.8(6) . . ?
C13 C12 S1 111.8(6) . . ?
C13 C12 H12A 109.3 . . ?
S1 C12 H12A 109.3 . . ?
C13 C12 H12B 109.3 . . ?
S1 C12 H12B 109.3 . . ?
H12A C12 H12B 107.9 . . ?
C14 C13 C17 117.4(8) . . ?
C14 C13 C12 123.3(7) . . ?
C17 C13 C12 119.2(8) . . ?
C15 C14 C13 120.0(7) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C16 C15 C14 119.4(8) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C15 C16 N6 121.9(8) . . ?
C15 C16 H16 119.0 . . ?
N6 C16 H16 119.0 . . ?
N6 C17 C13 122.4(7) . . ?
N6 C17 H17 118.8 . . ?
C13 C17 H17 118.8 . . ?
O1 C18 N7 128.1(17) . . ?
O1 C18 H18 115.9 . . ?
N7 C18 H18 115.9 . . ?
N7 C20 H20A 109.5 . . ?
N7 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N7 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N7 C21 H21A 109.5 . . ?
N7 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N7 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O2 C22 C23 107(2) . . ?
O2 C22 H22A 110.4 . . ?
C23 C22 H22A 110.4 . . ?
O2 C22 H22B 110.4 . . ?
C23 C22 H22B 110.4 . . ?
H22A C22 H22B 108.6 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N6 Cu1 N1 168.3(3) 2_655 . ?
N6 Cu1 O1 96.1(3) 2_655 . ?
N1 Cu1 O1 95.3(3) . . ?
N6 Cu1 Br2 89.6(2) 2_655 . ?
N1 Cu1 Br2 91.2(2) . . ?
O1 Cu1 Br2 100.2(4) . . ?
N6 Cu1 Br1 89.4(2) 2_655 . ?
N1 Cu1 Br1 86.1(2) . . ?
O1 Cu1 Br1 98.6(4) . . ?
Br2 Cu1 Br1 161.19(8) . . ?
C1 N1 C5 119.3(8) . . ?
C1 N1 Cu1 120.6(6) . . ?
C5 N1 Cu1 120.0(6) . . ?
C10 N2 N3 108.3(7) . . ?
C11 N3 N2 106.4(7) . . ?
C11 N4 C10 105.1(7) . . ?
C11 N4 N5 120.3(7) . . ?
C10 N4 N5 134.2(8) . . ?
N4 N5 H5A 111.1 . . ?
N4 N5 H5B 110.6 . . ?
H5A N5 H5B 106.9 . . ?
C17 N6 C16 118.9(7) . . ?
C17 N6 Cu1 121.8(5) . 2_654 ?
C16 N6 Cu1 119.1(6) . 2_654 ?
C18 N7 C21 117(2) . . ?
C18 N7 C20 121.2(17) . . ?
C21 N7 C20 120.8(17) . . ?
C18 O1 Cu1 132.6(14) . . ?
C22 O2 H2 109.5 . . ?
C11 S1 C12 97.6(4) . . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        70.94
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         1.355
_refine_diff_density_min         -1.348
_refine_diff_density_rms         0.146
####################################################################### 
# 
# 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_exp_1408
_database_code_depnum_ccdc_archive 'CCDC 1586108'
_audit_update_record             
;
2017-11-17 deposited with the CCDC.
2018-06-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H26 Br2 Cu N6 O2 S'
_chemical_formula_weight         661.91

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'
Br Br -0.6763 1.2805 '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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P n a 21'

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

_cell_length_a                   8.8761(3)
_cell_length_b                   15.2703(5)
_cell_length_c                   21.1399(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2865.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2914
_cell_measurement_theta_min      5.7810
_cell_measurement_theta_max      70.0680

_exptl_crystal_description       needle
_exptl_crystal_colour            'clear light green'
_exptl_crystal_size_max          0.3900
_exptl_crystal_size_mid          0.0700
_exptl_crystal_size_min          0.0600
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1324
_exptl_absorpt_coefficient_mu    5.260
_exptl_absorpt_correction_T_min  0.28527
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34k (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,16:31:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      298(2)
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.0793
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         7088
_diffrn_standards_interval_count 1.0000
_diffrn_standards_interval_time  1.0000
_diffrn_standards_decay_%        none
_diffrn_reflns_number            7040
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_av_sigmaI/netI    0.0285
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.57
_diffrn_reflns_theta_max         70.80
_reflns_number_total             4114
_reflns_number_gt                3739
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34k (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,16:31:05)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34k (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,16:31:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34k (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,16:31:05)
;
_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)+(0.0973P)²+0.5674P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00
_refine_ls_number_reflns         4114
_refine_ls_number_parameters     326
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0460
_refine_ls_wR_factor_ref         0.1473
_refine_ls_wR_factor_gt          0.1388
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.090
_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
Br2 Br 0.97699(11) 0.48516(5) 0.53479(5) 0.0638(3) Uani 1 1 d . . .
Br1 Br 0.54558(9) 0.51523(5) 0.67405(5) 0.0665(3) Uani 1 1 d . . .
C1 C 0.8380(7) 0.6921(4) 0.6307(3) 0.0469(14) Uani 1 1 d . . .
H1 H 0.9033 0.6747 0.6627 0.056 Uiso 1 1 calc R . .
C2 C 0.8183(7) 0.7827(4) 0.6200(4) 0.0513(15) Uani 1 1 d . . .
H2 H 0.8696 0.8237 0.6444 0.062 Uiso 1 1 calc R . .
C3 C 0.7236(8) 0.8089(4) 0.5735(4) 0.0477(15) Uani 1 1 d . . .
H3 H 0.7086 0.8683 0.5660 0.057 Uiso 1 1 calc R . .
C4 C 0.6484(6) 0.7465(4) 0.5367(3) 0.0388(12) Uani 1 1 d . . .
C5 C 0.6756(6) 0.6566(4) 0.5494(3) 0.0406(13) Uani 1 1 d . . .
C6 C 0.6023(8) 0.5923(4) 0.5117(4) 0.0494(15) Uani 1 1 d . . .
H6 H 0.6195 0.5332 0.5196 0.059 Uiso 1 1 calc R . .
C7 C 0.5073(8) 0.6164(4) 0.4645(4) 0.0488(15) Uani 1 1 d . . .
H7 H 0.4629 0.5735 0.4395 0.059 Uiso 1 1 calc R . .
C8 C 0.4741(6) 0.7071(4) 0.4524(3) 0.0389(12) Uani 1 1 d . . .
C9 C 0.5460(7) 0.7698(4) 0.4877(3) 0.0431(13) Uani 1 1 d . . .
H9 H 0.5275 0.8286 0.4794 0.052 Uiso 1 1 calc R . .
C10 C 0.3620(7) 0.7251(4) 0.4038(3) 0.0402(13) Uani 1 1 d . . .
C11 C 0.2156(7) 0.7851(4) 0.3342(3) 0.0403(13) Uani 1 1 d . . .
C12 C 0.0287(7) 0.7975(4) 0.2329(3) 0.0430(13) Uani 1 1 d . . .
H12A H -0.0215 0.7516 0.2567 0.052 Uiso 1 1 calc R . .
H12B H -0.0483 0.8324 0.2123 0.052 Uiso 1 1 calc R . .
C13 C 0.1265(7) 0.7565(4) 0.1835(3) 0.0413(12) Uani 1 1 d . . .
C14 C 0.1307(6) 0.6656(4) 0.1772(3) 0.0411(12) Uani 1 1 d . . .
H14 H 0.0762 0.6313 0.2054 0.049 Uiso 1 1 calc R . .
C15 C 0.2918(8) 0.6753(5) 0.0914(4) 0.0531(16) Uani 1 1 d . . .
H15 H 0.3491 0.6477 0.0604 0.064 Uiso 1 1 calc R . .
C16 C 0.2923(9) 0.7649(5) 0.0944(4) 0.0557(17) Uani 1 1 d . . .
H16 H 0.3482 0.7975 0.0656 0.067 Uiso 1 1 calc R . .
C17 C 0.2078(8) 0.8065(4) 0.1412(3) 0.0466(14) Uani 1 1 d . . .
H17 H 0.2062 0.8673 0.1438 0.056 Uiso 1 1 calc R . .
C18 C 1.1029(12) 0.5340(8) 0.7088(7) 0.088(3) Uani 1 1 d . . .
H18A H 1.1409 0.5501 0.6674 0.106 Uiso 1 1 calc R . .
H18B H 1.1446 0.4773 0.7200 0.106 Uiso 1 1 calc R . .
C19 C 1.1490(18) 0.5998(16) 0.7559(10) 0.159(8) Uani 1 1 d . . .
H19A H 1.1594 0.6575 0.7373 0.191 Uiso 1 1 calc R . .
H19B H 1.2422 0.5837 0.7769 0.191 Uiso 1 1 calc R . .
C20 C 1.017(3) 0.5947(16) 0.7996(11) 0.196(11) Uani 1 1 d . . .
H20A H 0.9800 0.6533 0.8078 0.235 Uiso 1 1 calc R . .
H20B H 1.0490 0.5695 0.8395 0.235 Uiso 1 1 calc R . .
C21 C 0.8839(18) 0.5368(14) 0.7708(7) 0.128(6) Uani 1 1 d . . .
H21A H 0.8754 0.4804 0.7916 0.153 Uiso 1 1 calc R . .
H21B H 0.7878 0.5669 0.7722 0.153 Uiso 1 1 calc R . .
C22 C 0.385(4) 0.368(4) 0.434(3) 0.34(6) Uani 0.50 1 d PD A 1
H22A H 0.3086 0.4086 0.4459 0.507 Uiso 0.50 1 calc PR A 1
H22B H 0.3597 0.3104 0.4485 0.507 Uiso 0.50 1 calc PR A 1
H22C H 0.3933 0.3669 0.3882 0.507 Uiso 0.50 1 calc PR A 1
C22' C 0.459(6) 0.379(5) 0.345(3) 0.26(4) Uani 0.50 1 d PD B 2
H22D H 0.4937 0.3485 0.3078 0.385 Uiso 0.50 1 calc PR B 2
H22E H 0.4277 0.4374 0.3326 0.385 Uiso 0.50 1 calc PR B 2
H22F H 0.3751 0.3487 0.3627 0.385 Uiso 0.50 1 calc PR B 2
Cu1 Cu 0.78899(11) 0.50374(5) 0.61927(6) 0.0442(2) Uani 1 1 d . . .
N1 N 0.7684(6) 0.6311(3) 0.5976(3) 0.0441(12) Uani 1 1 d . . .
N2 N 0.2772(6) 0.6629(3) 0.3785(3) 0.0455(12) Uani 1 1 d . . .
N3 N 0.1835(6) 0.7022(4) 0.3341(3) 0.0471(12) Uani 1 1 d . . .
N4 N 0.3254(6) 0.8041(3) 0.3765(3) 0.0406(11) Uani 1 1 d . . .
N5 N 0.3892(7) 0.8871(3) 0.3838(3) 0.0495(13) Uani 1 1 d . . .
H5A H 0.3624 0.9209 0.3525 0.059 Uiso 1 1 d R . .
H5B H 0.4874 0.8835 0.3839 0.059 Uiso 1 1 d R . .
N6 N 0.2113(6) 0.6262(3) 0.1315(3) 0.0448(12) Uani 1 1 d . . .
O1 O 0.9403(7) 0.5289(4) 0.7071(3) 0.0605(13) Uani 1 1 d . . .
O1" O 0.529(2) 0.3944(12) 0.4606(9) 0.107(6) Uani 0.50 1 d PD A 1
H1" H 0.5818 0.3834 0.4298 0.160 Uiso 0.50 1 d PR A 1
O1' O 0.579(4) 0.385(2) 0.390(2) 0.229(19) Uani 0.50 1 d PD B 2
H1' H 0.5599 0.4157 0.4212 0.343 Uiso 0.50 1 d PR B 2
S1 S 0.13454(18) 0.86739(10) 0.28803(8) 0.0451(3) 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
Br2 Cu1 2.4606(14) . ?
Br1 Cu1 2.4575(13) . ?
C1 N1 1.319(8) . ?
C1 C2 1.413(9) . ?
C1 H1 0.9300 . ?
C2 C3 1.353(11) . ?
C2 H2 0.9300 . ?
C3 C4 1.399(9) . ?
C3 H3 0.9300 . ?
C4 C5 1.420(8) . ?
C4 C9 1.423(9) . ?
C5 N1 1.368(8) . ?
C5 C6 1.422(9) . ?
C6 C7 1.358(11) . ?
C6 H6 0.9300 . ?
C7 C8 1.438(9) . ?
C7 H7 0.9300 . ?
C8 C9 1.371(9) . ?
C8 C10 1.458(9) . ?
C9 H9 0.9300 . ?
C10 N2 1.325(8) . ?
C10 N4 1.376(8) . ?
C11 N3 1.298(9) . ?
C11 N4 1.354(8) . ?
C11 S1 1.747(6) . ?
C12 C13 1.496(9) . ?
C12 S1 1.838(7) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C17 1.380(9) . ?
C13 C14 1.394(8) . ?
C14 N6 1.343(8) . ?
C14 H14 0.9300 . ?
C15 N6 1.339(9) . ?
C15 C16 1.369(10) . ?
C15 H15 0.9300 . ?
C16 C17 1.395(10) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 O1 1.445(12) . ?
C18 C19 1.47(2) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.49(3) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C21 1.60(2) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 O1 1.441(17) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 O1" 1.452(10) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C22' O1' 1.446(10) . ?
C22' H22D 0.9600 . ?
C22' H22E 0.9600 . ?
C22' H22F 0.9600 . ?
Cu1 N6 2.002(5) 2_665 ?
Cu1 N1 2.006(5) . ?
Cu1 O1 2.324(6) . ?
N2 N3 1.389(8) . ?
N4 N5 1.397(7) . ?
N5 H5A 0.8734 . ?
N5 H5B 0.8735 . ?
N6 Cu1 2.002(5) 2_664 ?
O1" H1" 0.8200 . ?
O1" H1' 0.9353 . ?
O1' H1" 0.8344 . ?
O1' H1' 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
N1 C1 C2 123.3(6) . . ?
N1 C1 H1 118.3 . . ?
C2 C1 H1 118.3 . . ?
C3 C2 C1 118.8(7) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C2 C3 C4 120.0(6) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C5 118.2(6) . . ?
C3 C4 C9 122.7(6) . . ?
C5 C4 C9 119.1(6) . . ?
N1 C5 C4 121.2(6) . . ?
N1 C5 C6 119.7(6) . . ?
C4 C5 C6 119.0(6) . . ?
C7 C6 C5 120.5(6) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C6 C7 C8 121.3(7) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 H7 119.4 . . ?
C9 C8 C7 118.7(6) . . ?
C9 C8 C10 124.7(6) . . ?
C7 C8 C10 116.6(6) . . ?
C8 C9 C4 121.3(6) . . ?
C8 C9 H9 119.4 . . ?
C4 C9 H9 119.4 . . ?
N2 C10 N4 109.0(5) . . ?
N2 C10 C8 122.5(5) . . ?
N4 C10 C8 128.5(6) . . ?
N3 C11 N4 111.6(6) . . ?
N3 C11 S1 127.6(5) . . ?
N4 C11 S1 120.8(5) . . ?
C13 C12 S1 112.9(4) . . ?
C13 C12 H12A 109.0 . . ?
S1 C12 H12A 109.0 . . ?
C13 C12 H12B 109.0 . . ?
S1 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
C17 C13 C14 118.4(6) . . ?
C17 C13 C12 121.6(5) . . ?
C14 C13 C12 119.9(6) . . ?
N6 C14 C13 121.9(6) . . ?
N6 C14 H14 119.0 . . ?
C13 C14 H14 119.0 . . ?
N6 C15 C16 122.1(7) . . ?
N6 C15 H15 119.0 . . ?
C16 C15 H15 119.0 . . ?
C15 C16 C17 119.1(7) . . ?
C15 C16 H16 120.4 . . ?
C17 C16 H16 120.4 . . ?
C13 C17 C16 119.2(6) . . ?
C13 C17 H17 120.4 . . ?
C16 C17 H17 120.4 . . ?
O1 C18 C19 109.4(11) . . ?
O1 C18 H18A 109.8 . . ?
C19 C18 H18A 109.8 . . ?
O1 C18 H18B 109.8 . . ?
C19 C18 H18B 109.8 . . ?
H18A C18 H18B 108.2 . . ?
C18 C19 C20 99.4(13) . . ?
C18 C19 H19A 111.9 . . ?
C20 C19 H19A 111.9 . . ?
C18 C19 H19B 111.9 . . ?
C20 C19 H19B 111.9 . . ?
H19A C19 H19B 109.6 . . ?
C19 C20 C21 111.9(16) . . ?
C19 C20 H20A 109.2 . . ?
C21 C20 H20A 109.2 . . ?
C19 C20 H20B 109.2 . . ?
C21 C20 H20B 109.2 . . ?
H20A C20 H20B 107.9 . . ?
O1 C21 C20 98.4(14) . . ?
O1 C21 H21A 112.1 . . ?
C20 C21 H21A 112.1 . . ?
O1 C21 H21B 112.1 . . ?
C20 C21 H21B 112.1 . . ?
H21A C21 H21B 109.7 . . ?
O1" C22 H22A 109.5 . . ?
O1" C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O1" C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O1' C22' H22D 109.5 . . ?
O1' C22' H22E 109.5 . . ?
H22D C22' H22E 109.5 . . ?
O1' C22' H22F 109.5 . . ?
H22D C22' H22F 109.5 . . ?
H22E C22' H22F 109.5 . . ?
N6 Cu1 N1 172.2(2) 2_665 . ?
N6 Cu1 O1 93.5(2) 2_665 . ?
N1 Cu1 O1 94.3(2) . . ?
N6 Cu1 Br1 90.50(16) 2_665 . ?
N1 Cu1 Br1 87.60(16) . . ?
O1 Cu1 Br1 96.89(17) . . ?
N6 Cu1 Br2 88.88(17) 2_665 . ?
N1 Cu1 Br2 90.46(17) . . ?
O1 Cu1 Br2 101.94(16) . . ?
Br1 Cu1 Br2 161.16(7) . . ?
C1 N1 C5 118.4(5) . . ?
C1 N1 Cu1 121.5(4) . . ?
C5 N1 Cu1 120.1(4) . . ?
C10 N2 N3 107.7(5) . . ?
C11 N3 N2 106.7(5) . . ?
C11 N4 C10 105.0(5) . . ?
C11 N4 N5 124.0(5) . . ?
C10 N4 N5 130.8(5) . . ?
N4 N5 H5A 109.9 . . ?
N4 N5 H5B 110.4 . . ?
H5A N5 H5B 108.1 . . ?
C15 N6 C14 119.3(5) . . ?
C15 N6 Cu1 118.2(5) . 2_664 ?
C14 N6 Cu1 122.5(4) . 2_664 ?
C21 O1 C18 108.6(9) . . ?
C21 O1 Cu1 124.0(7) . . ?
C18 O1 Cu1 127.3(7) . . ?
C22 O1" H1" 97.7 . . ?
C22 O1" H1' 90.3 . . ?
H1" O1" H1' 36.5 . . ?
C22' O1' H1" 133.5 . . ?
C22' O1' H1' 114.3 . . ?
H1" O1' H1' 39.6 . . ?
C11 S1 C12 98.5(3) . . ?

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 C1 C2 C3 0.0(11) . . . . ?
C1 C2 C3 C4 -0.6(11) . . . . ?
C2 C3 C4 C5 -0.5(10) . . . . ?
C2 C3 C4 C9 179.2(7) . . . . ?
C3 C4 C5 N1 2.4(9) . . . . ?
C9 C4 C5 N1 -177.4(6) . . . . ?
C3 C4 C5 C6 -178.9(6) . . . . ?
C9 C4 C5 C6 1.4(9) . . . . ?
N1 C5 C6 C7 178.6(7) . . . . ?
C4 C5 C6 C7 -0.1(10) . . . . ?
C5 C6 C7 C8 -2.1(11) . . . . ?
C6 C7 C8 C9 3.1(11) . . . . ?
C6 C7 C8 C10 -175.5(6) . . . . ?
C7 C8 C9 C4 -1.9(9) . . . . ?
C10 C8 C9 C4 176.6(6) . . . . ?
C3 C4 C9 C8 179.9(6) . . . . ?
C5 C4 C9 C8 -0.3(9) . . . . ?
C9 C8 C10 N2 -168.3(6) . . . . ?
C7 C8 C10 N2 10.3(9) . . . . ?
C9 C8 C10 N4 11.9(10) . . . . ?
C7 C8 C10 N4 -169.6(6) . . . . ?
S1 C12 C13 C17 -60.8(7) . . . . ?
S1 C12 C13 C14 122.6(6) . . . . ?
C17 C13 C14 N6 0.1(9) . . . . ?
C12 C13 C14 N6 176.8(6) . . . . ?
N6 C15 C16 C17 0.7(12) . . . . ?
C14 C13 C17 C16 -0.8(10) . . . . ?
C12 C13 C17 C16 -177.4(6) . . . . ?
C15 C16 C17 C13 0.4(11) . . . . ?
O1 C18 C19 C20 28(2) . . . . ?
C18 C19 C20 C21 -9(3) . . . . ?
C19 C20 C21 O1 -11(2) . . . . ?
C2 C1 N1 C5 1.8(10) . . . . ?
C2 C1 N1 Cu1 -175.4(5) . . . . ?
C4 C5 N1 C1 -3.0(9) . . . . ?
C6 C5 N1 C1 178.3(6) . . . . ?
C4 C5 N1 Cu1 174.3(4) . . . . ?
C6 C5 N1 Cu1 -4.5(8) . . . . ?
N6 Cu1 N1 C1 175.1(17) 2_665 . . . ?
O1 Cu1 N1 C1 2.3(5) . . . . ?
Br1 Cu1 N1 C1 99.0(5) . . . . ?
Br2 Cu1 N1 C1 -99.7(5) . . . . ?
N6 Cu1 N1 C5 -2(2) 2_665 . . . ?
O1 Cu1 N1 C5 -174.9(5) . . . . ?
Br1 Cu1 N1 C5 -78.2(5) . . . . ?
Br2 Cu1 N1 C5 83.1(5) . . . . ?
N4 C10 N2 N3 -0.1(7) . . . . ?
C8 C10 N2 N3 180.0(5) . . . . ?
N4 C11 N3 N2 -0.4(7) . . . . ?
S1 C11 N3 N2 179.8(5) . . . . ?
C10 N2 N3 C11 0.3(7) . . . . ?
N3 C11 N4 C10 0.3(7) . . . . ?
S1 C11 N4 C10 -179.9(4) . . . . ?
N3 C11 N4 N5 175.7(6) . . . . ?
S1 C11 N4 N5 -4.6(8) . . . . ?
N2 C10 N4 C11 -0.1(7) . . . . ?
C8 C10 N4 C11 179.8(6) . . . . ?
N2 C10 N4 N5 -175.0(6) . . . . ?
C8 C10 N4 N5 4.9(11) . . . . ?
C16 C15 N6 C14 -1.4(11) . . . . ?
C16 C15 N6 Cu1 176.7(6) . . . 2_664 ?
C13 C14 N6 C15 1.0(10) . . . . ?
C13 C14 N6 Cu1 -177.1(5) . . . 2_664 ?
C20 C21 O1 C18 28.4(17) . . . . ?
C20 C21 O1 Cu1 -154.9(11) . . . . ?
C19 C18 O1 C21 -38.7(17) . . . . ?
C19 C18 O1 Cu1 144.7(12) . . . . ?
N6 Cu1 O1 C21 -85.0(11) 2_665 . . . ?
N1 Cu1 O1 C21 94.0(11) . . . . ?
Br1 Cu1 O1 C21 5.9(11) . . . . ?
Br2 Cu1 O1 C21 -174.6(11) . . . . ?
N6 Cu1 O1 C18 91.1(7) 2_665 . . . ?
N1 Cu1 O1 C18 -89.9(7) . . . . ?
Br1 Cu1 O1 C18 -178.0(7) . . . . ?
Br2 Cu1 O1 C18 1.5(7) . . . . ?
N3 C11 S1 C12 -10.8(7) . . . . ?
N4 C11 S1 C12 169.5(5) . . . . ?
C13 C12 S1 C11 -76.9(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        70.80
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.565
_refine_diff_density_min         -0.691
_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_exp_1692
_database_code_depnum_ccdc_archive 'CCDC 1586107'
_audit_update_record             
;
2017-11-17 deposited with the CCDC.
2018-06-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18.50 H16.25 Br2 Cu N6.75 S'
_chemical_formula_weight         588.55

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'
Br Br -0.6763 1.2805 '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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P n a 21'

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

_cell_length_a                   8.4816(6)
_cell_length_b                   15.3597(17)
_cell_length_c                   19.7243(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2569.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    112(19)
_cell_measurement_reflns_used    1333
_cell_measurement_theta_min      4.4870
_cell_measurement_theta_max      65.8680

_exptl_crystal_description       needle
_exptl_crystal_colour            'clear dark brown'
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.040
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.521
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1158
_exptl_absorpt_coefficient_mu    5.741
_exptl_absorpt_correction_T_min  0.73924
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.641
_oxdiff_exptl_absorpt_empirical_full_max 1.524
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;

_diffrn_ambient_temperature      112(19)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.0793
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         6212
_diffrn_standards_interval_count 1.00
_diffrn_standards_interval_time  2.92
_diffrn_standards_decay_%        none
_diffrn_reflns_number            5568
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_sigmaI/netI    0.0527
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.65
_diffrn_reflns_theta_max         67.07
_reflns_number_total             3490
_reflns_number_gt                2868
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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)+(0.1439P)²+4.1063P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0015(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.45(7)
_refine_ls_number_reflns         3490
_refine_ls_number_parameters     310
_refine_ls_number_restraints     37
_refine_ls_R_factor_all          0.0954
_refine_ls_R_factor_gt           0.0843
_refine_ls_wR_factor_ref         0.2420
_refine_ls_wR_factor_gt          0.2284
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.060
_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
N6 N 0.1882(11) 0.6267(8) 0.8634(6) 0.066(3) Uani 1 1 d . . .
Br2 Br 1.03079(16) 0.51211(8) 0.29051(8) 0.0660(5) Uani 1 1 d . A .
Cu1 Cu 0.8336(2) 0.49923(13) 0.38022(13) 0.0654(6) Uani 1 1 d . . .
S1 S 0.8158(6) 0.8851(3) 0.5307(2) 0.0955(16) Uani 1 1 d . A .
N4 N 0.6271(14) 0.8156(7) 0.6261(7) 0.071(3) Uani 1 1 d . . .
C8 C 0.5957(16) 0.7367(9) 0.6543(8) 0.065(4) Uani 1 1 d . . .
C17 C 0.1209(16) 0.6854(10) 0.9038(8) 0.069(4) Uani 1 1 d . . .
H17 H 0.0573 0.6646 0.9386 0.083 Uiso 1 1 calc R . .
C12 C 0.2823(14) 0.6564(9) 0.8121(7) 0.056(3) Uani 1 1 d . . .
N3 N 0.6888(12) 0.6777(8) 0.6263(7) 0.070(3) Uani 1 1 d . . .
C15 C 0.2355(17) 0.8059(10) 0.8457(8) 0.070(4) Uani 1 1 d . . .
H15 H 0.2519 0.8653 0.8401 0.084 Uiso 1 1 calc R . .
C13 C 0.3537(14) 0.5947(8) 0.7691(7) 0.063(3) Uani 1 1 d . . .
H13 H 0.3337 0.5356 0.7745 0.075 Uiso 1 1 calc R . .
N1 N 0.8120(12) 0.6287(7) 0.3783(6) 0.061(3) Uani 1 1 d . A .
C14 C 0.4528(14) 0.6234(9) 0.7194(8) 0.064(3) Uani 1 1 d . . .
H14 H 0.5026 0.5826 0.6919 0.077 Uiso 1 1 calc R . .
C11 C 0.3076(12) 0.7477(7) 0.8022(6) 0.052(3) Uani 1 1 d . . .
C5 C 0.8737(15) 0.6772(10) 0.4259(7) 0.064(3) Uani 1 1 d . . .
H5 H 0.9269 0.6509 0.4617 0.076 Uiso 1 1 calc R A .
N2 N 0.7791(14) 0.7199(9) 0.5757(7) 0.078(4) Uani 1 1 d . . .
C16 C 0.1382(15) 0.7764(10) 0.8982(8) 0.066(3) Uani 1 1 d . . .
H16 H 0.0879 0.8146 0.9277 0.079 Uiso 1 1 calc R . .
N5 N 0.5537(16) 0.8961(8) 0.6347(8) 0.090(4) Uani 1 1 d . . .
H5A H 0.4522 0.8877 0.6441 0.134 Uiso 1 1 d R . .
H5B H 0.5625 0.9264 0.5964 0.134 Uiso 1 1 d R . .
C7 C 0.7419(17) 0.8006(10) 0.5798(9) 0.076(4) Uani 1 1 d . . .
C6 C 0.9508(16) 0.8189(12) 0.4790(9) 0.087(6) Uani 1 1 d . . .
H6A H 1.0267 0.8567 0.4571 0.104 Uiso 1 1 calc R A .
H6B H 1.0083 0.7794 0.5083 0.104 Uiso 1 1 calc R . .
C9 C 0.4828(15) 0.7142(9) 0.7081(8) 0.063(3) Uani 1 1 d . . .
C10 C 0.4097(14) 0.7745(9) 0.7508(7) 0.060(3) Uani 1 1 d . . .
H10 H 0.4295 0.8336 0.7449 0.071 Uiso 1 1 calc R . .
C3 C 0.7821(17) 0.8071(10) 0.3734(8) 0.073(4) Uani 1 1 d . . .
H3 H 0.7765 0.8675 0.3714 0.088 Uiso 1 1 calc R A .
C4 C 0.8614(14) 0.7650(10) 0.4238(7) 0.062(3) Uani 1 1 d . A .
C1 C 0.7265(17) 0.6646(10) 0.3278(9) 0.077(4) Uani 1 1 d . . .
H1 H 0.6792 0.6294 0.2953 0.092 Uiso 1 1 calc R A .
C2 C 0.7096(18) 0.7542(10) 0.3247(10) 0.078(4) Uani 1 1 d . A .
H2 H 0.6501 0.7792 0.2902 0.093 Uiso 1 1 calc R . .
Br1 Br 0.5716(5) 0.4780(2) 0.4402(3) 0.1103(18) Uani 0.50 1 d P A 1
N7 N 0.989(4) 0.474(2) 0.4776(18) 0.099(9) Uani 0.50 1 d PDU A 1
C18 C 1.098(4) 0.456(3) 0.5064(19) 0.107(12) Uani 0.50 1 d PDU A 1
C19 C 1.201(5) 0.414(3) 0.562(2) 0.135(16) Uani 0.50 1 d PDU A 1
H19A H 1.2674 0.4577 0.5814 0.202 Uiso 0.50 1 calc PR A 1
H19B H 1.2643 0.3690 0.5421 0.202 Uiso 0.50 1 calc PR A 1
H19C H 1.1340 0.3896 0.5961 0.202 Uiso 0.50 1 calc PR A 1
N8 N 0.499(6) 0.367(5) 0.680(3) 0.099(12) Uani 0.25 1 d PDU B 1
C21 C 0.601(6) 0.397(5) 0.653(3) 0.099(12) Uani 0.25 1 d PDU B 1
C20 C 0.731(7) 0.453(5) 0.623(4) 0.098(12) Uani 0.25 1 d PDU B 1
H20A H 0.7542 0.4336 0.5780 0.147 Uiso 0.25 1 calc PR B 1
H20B H 0.8239 0.4489 0.6506 0.147 Uiso 0.25 1 calc PR B 1
H20C H 0.6969 0.5129 0.6215 0.147 Uiso 0.25 1 calc PR B 1
Br1' Br 0.7344(6) 0.4960(2) 0.4873(2) 0.0956(14) Uani 0.50 1 d P A 2


_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
N6 C17 1.331(19) . ?
N6 C12 1.369(17) . ?
N6 Cu1 1.970(12) 2_665 ?
Br2 Cu1 2.443(3) . ?
Cu1 N6 1.970(12) 2_664 ?
Cu1 N1 1.997(11) . ?
Cu1 Br1' 2.275(4) . ?
Cu1 N7 2.36(3) . ?
Cu1 Br1 2.538(4) . ?
S1 C7 1.737(16) . ?
S1 C6 1.840(14) . ?
N4 C7 1.355(18) . ?
N4 C8 1.361(19) . ?
N4 N5 1.395(16) . ?
C8 N3 1.322(16) . ?
C8 C9 1.47(2) . ?
C17 C16 1.41(2) . ?
C17 H17 0.9300 . ?
C12 C13 1.408(18) . ?
C12 C11 1.432(18) . ?
N3 N2 1.415(17) . ?
C15 C11 1.382(18) . ?
C15 C16 1.40(2) . ?
C15 H15 0.9300 . ?
C13 C14 1.364(19) . ?
C13 H13 0.9300 . ?
N1 C5 1.307(16) . ?
N1 C1 1.35(2) . ?
C14 C9 1.435(19) . ?
C14 H14 0.9300 . ?
C11 C10 1.395(18) . ?
C5 C4 1.35(2) . ?
C5 H5 0.9300 . ?
N2 C7 1.28(2) . ?
C16 H16 0.9300 . ?
N5 H5A 0.8900 . ?
N5 H5B 0.8900 . ?
C6 C4 1.563(19) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C9 C10 1.398(19) . ?
C10 H10 0.9300 . ?
C3 C4 1.36(2) . ?
C3 C2 1.40(2) . ?
C3 H3 0.9300 . ?
C1 C2 1.38(2) . ?
C1 H1 0.9300 . ?
C2 H2 0.9300 . ?
N7 C18 1.125(10) . ?
C18 C19 1.533(10) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
N8 C21 1.118(10) . ?
C21 C20 1.519(10) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 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
C17 N6 C12 117.8(12) . . ?
C17 N6 Cu1 121.6(10) . 2_665 ?
C12 N6 Cu1 120.4(9) . 2_665 ?
N6 Cu1 N1 164.9(5) 2_664 . ?
N6 Cu1 Br1' 95.8(4) 2_664 . ?
N1 Cu1 Br1' 90.3(3) . . ?
N6 Cu1 N7 91.7(9) 2_664 . ?
N1 Cu1 N7 103.2(9) . . ?
Br1' Cu1 N7 56.4(9) . . ?
N6 Cu1 Br2 91.2(3) 2_664 . ?
N1 Cu1 Br2 88.2(3) . . ?
Br1' Cu1 Br2 158.09(18) . . ?
N7 Cu1 Br2 102.7(9) . . ?
N6 Cu1 Br1 82.5(3) 2_664 . ?
N1 Cu1 Br1 93.2(3) . . ?
Br1' Cu1 Br1 40.6(2) . . ?
N7 Cu1 Br1 95.1(9) . . ?
Br2 Cu1 Br1 161.32(19) . . ?
C7 S1 C6 96.9(8) . . ?
C7 N4 C8 105.3(12) . . ?
C7 N4 N5 123.7(13) . . ?
C8 N4 N5 130.8(11) . . ?
N3 C8 N4 108.8(12) . . ?
N3 C8 C9 122.0(14) . . ?
N4 C8 C9 129.2(12) . . ?
N6 C17 C16 125.5(14) . . ?
N6 C17 H17 117.3 . . ?
C16 C17 H17 117.3 . . ?
N6 C12 C13 118.2(12) . . ?
N6 C12 C11 121.0(12) . . ?
C13 C12 C11 120.8(12) . . ?
C8 N3 N2 107.8(12) . . ?
C11 C15 C16 120.8(14) . . ?
C11 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C14 C13 C12 118.7(12) . . ?
C14 C13 H13 120.6 . . ?
C12 C13 H13 120.6 . . ?
C5 N1 C1 120.8(13) . . ?
C5 N1 Cu1 121.1(10) . . ?
C1 N1 Cu1 118.0(9) . . ?
C13 C14 C9 122.3(12) . . ?
C13 C14 H14 118.8 . . ?
C9 C14 H14 118.8 . . ?
C15 C11 C10 122.3(12) . . ?
C15 C11 C12 118.9(12) . . ?
C10 C11 C12 118.7(11) . . ?
N1 C5 C4 121.0(14) . . ?
N1 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C7 N2 N3 105.4(11) . . ?
C15 C16 C17 116.1(14) . . ?
C15 C16 H16 122.0 . . ?
C17 C16 H16 122.0 . . ?
N4 N5 H5A 109.1 . . ?
N4 N5 H5B 108.8 . . ?
H5A N5 H5B 109.5 . . ?
N2 C7 N4 112.6(13) . . ?
N2 C7 S1 126.8(12) . . ?
N4 C7 S1 120.5(12) . . ?
C4 C6 S1 112.1(9) . . ?
C4 C6 H6A 109.2 . . ?
S1 C6 H6A 109.2 . . ?
C4 C6 H6B 109.2 . . ?
S1 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
C10 C9 C14 118.1(14) . . ?
C10 C9 C8 124.7(13) . . ?
C14 C9 C8 117.1(12) . . ?
C11 C10 C9 121.2(13) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C4 C3 C2 116.2(14) . . ?
C4 C3 H3 121.9 . . ?
C2 C3 H3 121.9 . . ?
C5 C4 C3 122.1(13) . . ?
C5 C4 C6 118.0(14) . . ?
C3 C4 C6 119.8(14) . . ?
N1 C1 C2 119.7(15) . . ?
N1 C1 H1 120.2 . . ?
C2 C1 H1 120.2 . . ?
C1 C2 C3 120.0(17) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C18 N7 Cu1 156(3) . . ?
N7 C18 C19 159(4) . . ?
N8 C21 C20 170(8) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N4 C8 N3 0.5(17) . . . . ?
N5 N4 C8 N3 174.7(14) . . . . ?
C7 N4 C8 C9 179.1(14) . . . . ?
N5 N4 C8 C9 -7(3) . . . . ?
C12 N6 C17 C16 0(2) . . . . ?
Cu1 N6 C17 C16 175.8(10) 2_665 . . . ?
C17 N6 C12 C13 -179.9(12) . . . . ?
Cu1 N6 C12 C13 4.3(16) 2_665 . . . ?
C17 N6 C12 C11 0.1(17) . . . . ?
Cu1 N6 C12 C11 -175.7(8) 2_665 . . . ?
N4 C8 N3 N2 -2.7(15) . . . . ?
C9 C8 N3 N2 178.5(12) . . . . ?
N6 C12 C13 C14 -177.4(12) . . . . ?
C11 C12 C13 C14 2.6(19) . . . . ?
N6 Cu1 N1 C5 167.3(16) 2_664 . . . ?
Br1' Cu1 N1 C5 53.5(10) . . . . ?
N7 Cu1 N1 C5 -2.0(13) . . . . ?
Br2 Cu1 N1 C5 -104.6(10) . . . . ?
Br1 Cu1 N1 C5 94.0(10) . . . . ?
N6 Cu1 N1 C1 -10(3) 2_664 . . . ?
Br1' Cu1 N1 C1 -124.0(10) . . . . ?
N7 Cu1 N1 C1 -179.4(13) . . . . ?
Br2 Cu1 N1 C1 77.9(10) . . . . ?
Br1 Cu1 N1 C1 -83.4(10) . . . . ?
C12 C13 C14 C9 -2(2) . . . . ?
C16 C15 C11 C10 -177.7(12) . . . . ?
C16 C15 C11 C12 -0.6(19) . . . . ?
N6 C12 C11 C15 0.2(18) . . . . ?
C13 C12 C11 C15 -179.8(12) . . . . ?
N6 C12 C11 C10 177.4(11) . . . . ?
C13 C12 C11 C10 -2.6(17) . . . . ?
C1 N1 C5 C4 -3.8(19) . . . . ?
Cu1 N1 C5 C4 178.8(9) . . . . ?
C8 N3 N2 C7 4.0(16) . . . . ?
C11 C15 C16 C17 0.7(19) . . . . ?
N6 C17 C16 C15 0(2) . . . . ?
N3 N2 C7 N4 -3.8(19) . . . . ?
N3 N2 C7 S1 179.5(11) . . . . ?
C8 N4 C7 N2 2(2) . . . . ?
N5 N4 C7 N2 -172.5(13) . . . . ?
C8 N4 C7 S1 179.1(11) . . . . ?
N5 N4 C7 S1 4(2) . . . . ?
C6 S1 C7 N2 -0.5(17) . . . . ?
C6 S1 C7 N4 -176.9(14) . . . . ?
C7 S1 C6 C4 75.7(14) . . . . ?
C13 C14 C9 C10 1(2) . . . . ?
C13 C14 C9 C8 178.2(12) . . . . ?
N3 C8 C9 C10 163.6(13) . . . . ?
N4 C8 C9 C10 -15(2) . . . . ?
N3 C8 C9 C14 -13(2) . . . . ?
N4 C8 C9 C14 168.7(14) . . . . ?
C15 C11 C10 C9 179.1(12) . . . . ?
C12 C11 C10 C9 2.0(18) . . . . ?
C14 C9 C10 C11 -1.4(19) . . . . ?
C8 C9 C10 C11 -177.9(12) . . . . ?
N1 C5 C4 C3 1(2) . . . . ?
N1 C5 C4 C6 -174.7(11) . . . . ?
C2 C3 C4 C5 2(2) . . . . ?
C2 C3 C4 C6 177.9(11) . . . . ?
S1 C6 C4 C5 -119.7(13) . . . . ?
S1 C6 C4 C3 64.1(17) . . . . ?
C5 N1 C1 C2 3(2) . . . . ?
Cu1 N1 C1 C2 -179.7(11) . . . . ?
N1 C1 C2 C3 1(2) . . . . ?
C4 C3 C2 C1 -3(2) . . . . ?
N6 Cu1 N7 C18 73(8) 2_664 . . . ?
N1 Cu1 N7 C18 -109(8) . . . . ?
Br1' Cu1 N7 C18 169(9) . . . . ?
Br2 Cu1 N7 C18 -18(8) . . . . ?
Br1 Cu1 N7 C18 156(8) . . . . ?
Cu1 N7 C18 C19 -139(10) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        67.07
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.904
_refine_diff_density_min         -0.770
_refine_diff_density_rms         0.134
####################################################################### 
# 
# 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_exp_1687
_database_code_depnum_ccdc_archive 'CCDC 1586106'
_audit_update_record             
;
2017-11-17 deposited with the CCDC.
2018-06-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H24 Br2 Cl2 Cu N6 O2 S'
_chemical_formula_weight         706.77

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'
Cu Cu -1.9646 0.5888 '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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P n a 21'

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

_cell_length_a                   8.7520(2)
_cell_length_b                   15.3925(3)
_cell_length_c                   20.4584(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2756.06(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.01(10)
_cell_measurement_reflns_used    3256
_cell_measurement_theta_min      5.7520
_cell_measurement_theta_max      70.9380

_exptl_crystal_description       needle
_exptl_crystal_colour            'clear light green'
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.040
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.703
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1404
_exptl_absorpt_coefficient_mu    7.254
_exptl_absorpt_correction_T_min  0.56971
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.734
_oxdiff_exptl_absorpt_empirical_full_max 1.477
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;


_diffrn_ambient_temperature      100.01(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.0793
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         7323
_diffrn_standards_interval_count 1.00
_diffrn_standards_interval_time  1.00
_diffrn_standards_decay_%        none
_diffrn_reflns_number            6482
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_sigmaI/netI    0.0376
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.59
_diffrn_reflns_theta_max         67.07
_reflns_number_total             3412
_reflns_number_gt                3189
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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)+(0.0638P)²+5.0577P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00
_refine_ls_number_reflns         3412
_refine_ls_number_parameters     310
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0405
_refine_ls_wR_factor_ref         0.1107
_refine_ls_wR_factor_gt          0.1083
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.080
_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 0.47542(8) 1.01145(4) 0.84896(4) 0.0213(2) Uani 1 1 d . . .
Br2 Br 0.01032(9) 0.99012(5) 0.97486(4) 0.0236(2) Uani 1 1 d . . .
C1 C 0.8324(8) 0.8096(4) 0.3748(3) 0.0154(13) Uani 1 1 d . . .
H1 H 0.8939 0.8276 0.3403 0.018 Uiso 1 1 calc R . .
C2 C 0.8121(7) 0.7197(4) 0.3844(3) 0.0145(14) Uani 1 1 d . . .
H2A H 0.8618 0.6799 0.3575 0.017 Uiso 1 1 calc R . .
C3 C 0.7189(7) 0.6917(4) 0.4333(4) 0.0142(14) Uani 1 1 d . . .
H3 H 0.7023 0.6326 0.4397 0.017 Uiso 1 1 calc R . .
C4 C 0.6479(7) 0.7537(4) 0.4741(3) 0.0128(12) Uani 1 1 d . . .
C5 C 0.6781(7) 0.8431(4) 0.4637(3) 0.0131(13) Uani 1 1 d . . .
C6 C 0.6121(8) 0.9055(4) 0.5059(3) 0.0161(14) Uani 1 1 d . . .
H6 H 0.6343 0.9640 0.5002 0.019 Uiso 1 1 calc R . .
C7 C 0.5175(7) 0.8808(4) 0.5545(3) 0.0147(14) Uani 1 1 d . . .
H7 H 0.4764 0.9230 0.5819 0.018 Uiso 1 1 calc R . .
C8 C 0.4785(7) 0.7919(4) 0.5650(3) 0.0125(13) Uani 1 1 d . . .
C9 C 0.5458(7) 0.7290(4) 0.5255(3) 0.0128(13) Uani 1 1 d . . .
H9 H 0.5243 0.6706 0.5325 0.015 Uiso 1 1 calc R . .
C10 C 0.3640(7) 0.7735(4) 0.6144(3) 0.0118(12) Uani 1 1 d . . .
C11 C 0.2144(7) 0.7107(4) 0.6856(3) 0.0143(13) Uani 1 1 d . . .
C12 C 0.0264(7) 0.6988(4) 0.7884(3) 0.0134(14) Uani 1 1 d . . .
H12A H -0.0265 0.7429 0.7632 0.016 Uiso 1 1 calc R . .
H12B H -0.0502 0.6643 0.8107 0.016 Uiso 1 1 calc R . .
C13 C 0.1250(7) 0.7422(4) 0.8381(3) 0.0128(13) Uani 1 1 d . . .
C14 C 0.2087(7) 0.6951(4) 0.8834(4) 0.0156(14) Uani 1 1 d . . .
H14 H 0.2080 0.6347 0.8822 0.019 Uiso 1 1 calc R . .
C15 C 0.2933(9) 0.7384(4) 0.9305(4) 0.0193(15) Uani 1 1 d . . .
H15 H 0.3479 0.7075 0.9618 0.023 Uiso 1 1 calc R . .
C16 C 0.2952(8) 0.8284(4) 0.9301(4) 0.0183(15) Uani 1 1 d . . .
H16 H 0.3545 0.8575 0.9608 0.022 Uiso 1 1 calc R . .
C17 C 0.1312(7) 0.8314(4) 0.8415(3) 0.0139(13) Uani 1 1 d . . .
H17 H 0.0758 0.8635 0.8111 0.017 Uiso 1 1 calc R . .
C18 C -0.0651(10) 1.0348(5) 0.7855(4) 0.0331(19) Uani 1 1 d . . .
H18A H -0.1234 1.0162 0.8227 0.050 Uiso 1 1 calc R . .
H18B H -0.0919 1.0001 0.7483 0.050 Uiso 1 1 calc R . .
H18C H -0.0869 1.0947 0.7765 0.050 Uiso 1 1 calc R . .
C19 C 0.8074(12) 0.9376(6) 0.1300(5) 0.046(2) Uani 1 1 d . . .
H19A H 0.8372 0.9722 0.0931 0.069 Uiso 1 1 calc R . .
H19B H 0.7226 0.9013 0.1181 0.069 Uiso 1 1 calc R . .
H19C H 0.8917 0.9020 0.1434 0.069 Uiso 1 1 calc R . .
C20 C 0.4373(14) 0.8825(8) 0.1990(6) 0.064(3) Uani 1 1 d . . .
H20A H 0.5197 0.9246 0.1994 0.076 Uiso 1 1 calc R . .
H20B H 0.3688 0.8965 0.2347 0.076 Uiso 1 1 calc R . .
Cl1 Cl 0.5124(5) 0.7807(2) 0.2118(2) 0.0949(13) Uani 1 1 d . . .
Cl2 Cl 0.3322(5) 0.8923(3) 0.12116(19) 0.0987(13) Uani 1 1 d . . .
Cu3 Cu 0.21351(11) 1.00411(5) 0.89292(6) 0.0129(2) Uani 1 1 d . . .
N1 N 0.7693(6) 0.8696(4) 0.4119(3) 0.0151(12) Uani 1 1 d . . .
N2 N 0.2781(6) 0.8330(3) 0.6417(3) 0.0123(11) Uani 1 1 d . . .
N3 N 0.1816(6) 0.7941(3) 0.6868(3) 0.0128(11) Uani 1 1 d . . .
N4 N 0.3256(6) 0.6936(3) 0.6411(3) 0.0115(11) Uani 1 1 d . . .
N5 N 0.3899(6) 0.6114(4) 0.6349(3) 0.0154(12) Uani 1 1 d . . .
H5A H 0.3824 0.6005 0.5894 0.023 Uiso 1 1 d R . .
H5B H 0.4902 0.6198 0.6483 0.023 Uiso 1 1 d R . .
N6 N 0.2139(6) 0.8749(3) 0.8868(3) 0.0153(11) Uani 1 1 d . . .
O1 O 0.0941(6) 1.0250(3) 0.7991(2) 0.0191(10) Uani 1 1 d . . .
H1A H 0.1574 1.0278 0.7627 0.023 Uiso 1 1 calc R . .
O2 O 0.7647(9) 0.9919(3) 0.1813(3) 0.0383(16) Uani 1 1 d . . .
H2 H 0.7420 1.0399 0.1669 0.057 Uiso 1 1 calc R . .
S1 S 0.13286(17) 0.62884(9) 0.73253(9) 0.0137(3) 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
Br1 Cu3 2.4650(12) . ?
Br2 Cu3 2.4533(13) . ?
C1 N1 1.316(9) . ?
C1 C2 1.409(8) . ?
C1 H1 0.9300 . ?
C2 C3 1.361(10) . ?
C2 H2A 0.9300 . ?
C3 C4 1.413(9) . ?
C3 H3 0.9300 . ?
C4 C5 1.419(9) . ?
C4 C9 1.431(9) . ?
C5 N1 1.388(8) . ?
C5 C6 1.415(9) . ?
C6 C7 1.347(10) . ?
C6 H6 0.9300 . ?
C7 C8 1.426(9) . ?
C7 H7 0.9300 . ?
C8 C9 1.391(10) . ?
C8 C10 1.452(9) . ?
C9 H9 0.9300 . ?
C10 N2 1.309(8) . ?
C10 N4 1.387(8) . ?
C11 N3 1.316(8) . ?
C11 N4 1.358(8) . ?
C11 S1 1.738(7) . ?
C12 C13 1.491(9) . ?
C12 S1 1.826(7) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C17 1.376(8) . ?
C13 C14 1.386(9) . ?
C14 C15 1.386(10) . ?
C14 H14 0.9300 . ?
C15 C16 1.385(9) . ?
C15 H15 0.9300 . ?
C16 N6 1.343(9) . ?
C16 H16 0.9300 . ?
C17 N6 1.354(9) . ?
C17 H17 0.9300 . ?
C18 O1 1.428(9) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 O2 1.393(10) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 Cl1 1.718(13) . ?
C20 Cl2 1.845(13) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
Cu3 N1 1.988(6) 2_675 ?
Cu3 N6 1.993(5) . ?
Cu3 O1 2.209(5) . ?
N1 Cu3 1.988(6) 2_674 ?
N2 N3 1.387(7) . ?
N4 N5 1.392(7) . ?
N5 H5A 0.9487 . ?
N5 H5B 0.9284 . ?
O1 H1A 0.9300 . ?
O2 H2 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
N1 C1 C2 123.8(6) . . ?
N1 C1 H1 118.1 . . ?
C2 C1 H1 118.1 . . ?
C3 C2 C1 119.2(6) . . ?
C3 C2 H2A 120.4 . . ?
C1 C2 H2A 120.4 . . ?
C2 C3 C4 119.0(6) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C3 C4 C5 119.0(6) . . ?
C3 C4 C9 122.1(6) . . ?
C5 C4 C9 119.0(6) . . ?
N1 C5 C6 120.2(6) . . ?
N1 C5 C4 120.5(6) . . ?
C6 C5 C4 119.3(6) . . ?
C7 C6 C5 120.7(6) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C7 C8 121.8(6) . . ?
C6 C7 H7 119.1 . . ?
C8 C7 H7 119.1 . . ?
C9 C8 C7 118.6(6) . . ?
C9 C8 C10 124.1(6) . . ?
C7 C8 C10 117.2(6) . . ?
C8 C9 C4 120.4(6) . . ?
C8 C9 H9 119.8 . . ?
C4 C9 H9 119.8 . . ?
N2 C10 N4 108.2(6) . . ?
N2 C10 C8 123.9(6) . . ?
N4 C10 C8 127.9(6) . . ?
N3 C11 N4 111.0(6) . . ?
N3 C11 S1 127.4(5) . . ?
N4 C11 S1 121.7(5) . . ?
C13 C12 S1 113.3(4) . . ?
C13 C12 H12A 108.9 . . ?
S1 C12 H12A 108.9 . . ?
C13 C12 H12B 108.9 . . ?
S1 C12 H12B 108.9 . . ?
H12A C12 H12B 107.7 . . ?
C17 C13 C14 117.8(6) . . ?
C17 C13 C12 120.3(6) . . ?
C14 C13 C12 121.8(6) . . ?
C13 C14 C15 119.8(6) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C16 C15 C14 118.9(7) . . ?
C16 C15 H15 120.6 . . ?
C14 C15 H15 120.6 . . ?
N6 C16 C15 122.0(7) . . ?
N6 C16 H16 119.0 . . ?
C15 C16 H16 119.0 . . ?
N6 C17 C13 123.3(6) . . ?
N6 C17 H17 118.4 . . ?
C13 C17 H17 118.4 . . ?
O1 C18 H18A 109.5 . . ?
O1 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O1 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O2 C19 H19A 109.5 . . ?
O2 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O2 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
Cl1 C20 Cl2 113.4(7) . . ?
Cl1 C20 H20A 108.9 . . ?
Cl2 C20 H20A 108.9 . . ?
Cl1 C20 H20B 108.9 . . ?
Cl2 C20 H20B 108.9 . . ?
H20A C20 H20B 107.7 . . ?
N1 Cu3 N6 171.1(2) 2_675 . ?
N1 Cu3 O1 93.6(2) 2_675 . ?
N6 Cu3 O1 95.2(2) . . ?
N1 Cu3 Br2 90.44(16) 2_675 . ?
N6 Cu3 Br2 87.50(16) . . ?
O1 Cu3 Br2 105.28(14) . . ?
N1 Cu3 Br1 87.47(16) 2_675 . ?
N6 Cu3 Br1 91.21(15) . . ?
O1 Cu3 Br1 96.68(15) . . ?
Br2 Cu3 Br1 158.03(6) . . ?
C1 N1 C5 118.4(6) . . ?
C1 N1 Cu3 122.8(5) . 2_674 ?
C5 N1 Cu3 118.6(4) . 2_674 ?
C10 N2 N3 109.4(5) . . ?
C11 N3 N2 106.0(5) . . ?
C11 N4 C10 105.4(5) . . ?
C11 N4 N5 121.7(5) . . ?
C10 N4 N5 132.3(5) . . ?
N4 N5 H5A 102.8 . . ?
N4 N5 H5B 103.2 . . ?
H5A N5 H5B 112.3 . . ?
C16 N6 C17 118.2(6) . . ?
C16 N6 Cu3 119.4(5) . . ?
C17 N6 Cu3 122.3(4) . . ?
C18 O1 Cu3 130.2(5) . . ?
C18 O1 H1A 114.9 . . ?
Cu3 O1 H1A 114.9 . . ?
C19 O2 H2 109.5 . . ?
C11 S1 C12 97.4(3) . . ?

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 C1 C2 C3 1.9(11) . . . . ?
C1 C2 C3 C4 -1.5(10) . . . . ?
C2 C3 C4 C5 -1.2(10) . . . . ?
C2 C3 C4 C9 178.5(6) . . . . ?
C3 C4 C5 N1 3.6(9) . . . . ?
C9 C4 C5 N1 -176.1(6) . . . . ?
C3 C4 C5 C6 -177.6(6) . . . . ?
C9 C4 C5 C6 2.7(9) . . . . ?
N1 C5 C6 C7 176.8(6) . . . . ?
C4 C5 C6 C7 -2.1(10) . . . . ?
C5 C6 C7 C8 -0.7(11) . . . . ?
C6 C7 C8 C9 2.8(10) . . . . ?
C6 C7 C8 C10 -174.0(6) . . . . ?
C7 C8 C9 C4 -2.1(10) . . . . ?
C10 C8 C9 C4 174.5(6) . . . . ?
C3 C4 C9 C8 179.7(6) . . . . ?
C5 C4 C9 C8 -0.6(10) . . . . ?
C9 C8 C10 N2 -165.0(6) . . . . ?
C7 C8 C10 N2 11.6(10) . . . . ?
C9 C8 C10 N4 15.1(11) . . . . ?
C7 C8 C10 N4 -168.2(6) . . . . ?
S1 C12 C13 C17 120.4(6) . . . . ?
S1 C12 C13 C14 -61.9(8) . . . . ?
C17 C13 C14 C15 0.8(10) . . . . ?
C12 C13 C14 C15 -177.1(6) . . . . ?
C13 C14 C15 C16 -1.6(11) . . . . ?
C14 C15 C16 N6 2.1(11) . . . . ?
C14 C13 C17 N6 -0.3(10) . . . . ?
C12 C13 C17 N6 177.5(6) . . . . ?
C2 C1 N1 C5 0.4(10) . . . . ?
C2 C1 N1 Cu3 -175.0(5) . . . 2_674 ?
C6 C5 N1 C1 178.0(6) . . . . ?
C4 C5 N1 C1 -3.2(9) . . . . ?
C6 C5 N1 Cu3 -6.4(8) . . . 2_674 ?
C4 C5 N1 Cu3 172.4(5) . . . 2_674 ?
N4 C10 N2 N3 0.1(7) . . . . ?
C8 C10 N2 N3 -179.8(5) . . . . ?
N4 C11 N3 N2 -1.0(7) . . . . ?
S1 C11 N3 N2 179.0(5) . . . . ?
C10 N2 N3 C11 0.5(7) . . . . ?
N3 C11 N4 C10 1.1(7) . . . . ?
S1 C11 N4 C10 -178.9(5) . . . . ?
N3 C11 N4 N5 174.0(5) . . . . ?
S1 C11 N4 N5 -6.0(8) . . . . ?
N2 C10 N4 C11 -0.7(7) . . . . ?
C8 C10 N4 C11 179.2(6) . . . . ?
N2 C10 N4 N5 -172.6(6) . . . . ?
C8 C10 N4 N5 7.3(11) . . . . ?
C15 C16 N6 C17 -1.6(10) . . . . ?
C15 C16 N6 Cu3 176.5(6) . . . . ?
C13 C17 N6 C16 0.7(9) . . . . ?
C13 C17 N6 Cu3 -177.3(5) . . . . ?
N1 Cu3 N6 C16 -7.2(18) 2_675 . . . ?
O1 Cu3 N6 C16 171.0(5) . . . . ?
Br2 Cu3 N6 C16 -83.9(5) . . . . ?
Br1 Cu3 N6 C16 74.2(5) . . . . ?
N1 Cu3 N6 C17 170.9(13) 2_675 . . . ?
O1 Cu3 N6 C17 -11.0(5) . . . . ?
Br2 Cu3 N6 C17 94.1(5) . . . . ?
Br1 Cu3 N6 C17 -107.8(5) . . . . ?
N1 Cu3 O1 C18 -87.5(5) 2_675 . . . ?
N6 Cu3 O1 C18 92.7(6) . . . . ?
Br2 Cu3 O1 C18 3.9(5) . . . . ?
Br1 Cu3 O1 C18 -175.4(5) . . . . ?
N3 C11 S1 C12 -9.8(7) . . . . ?
N4 C11 S1 C12 170.2(5) . . . . ?
C13 C12 S1 C11 -75.0(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
N5 H5B N2 0.93 2.63 3.507(8) 158.5 3_565
N5 H5B N3 0.93 2.28 3.124(8) 151.5 3_565
N5 H5A Br2 0.95 3.04 3.869(6) 146.4 4_544
O1 H1A O2 0.93 1.82 2.721(8) 161.2 2_675
O2 H2 N3 0.82 2.67 3.329(8) 138.2 2_674
O2 H2 N2 0.82 2.03 2.839(8) 168.6 2_674

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        67.07
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.866
_refine_diff_density_min         -0.889
_refine_diff_density_rms         0.117
