# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2015

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

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1002348'
_audit_update_record             
;
2015-01-30 deposited with the CCDC.
2015-02-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        SB-28
_chemical_name_common            ?
_chemical_formula_moiety         'C54 H44 Br Cl Cu N3 P2 S, C2 H6 O S'
_chemical_formula_sum            'C56 H50 Br Cl Cu N3 O P2 S2'
_exptl_crystal_recrystallization_method dichloromethane
_chemical_melting_point          ?

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_diffrn_ambient_temperature      200(2)
_chemical_formula_weight         1085.95

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   9.6604(5)
_cell_length_b                   13.1537(6)
_cell_length_c                   20.3412(10)
_cell_angle_alpha                99.305(4)
_cell_angle_beta                 94.696(4)
_cell_angle_gamma                93.570(4)
_cell_volume                     2534.7(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    22901
_cell_measurement_theta_min      1.57
_cell_measurement_theta_max      25.45
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1116
_exptl_absorpt_coefficient_mu    1.460
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.7026
_exptl_absorpt_correction_T_max  0.8921
_exptl_absorpt_process_details   
;
Stoe & Cie (2002). X-SHAPE. Stoe & Cie, Darmstadt, Germany
;
_exptl_special_details           
;
 ?
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean 6.67
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            48925
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_av_R_equivalents  0.0576
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.573
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             8938
_reflns_number_gt                6085
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'X-Area (Stoe & Cie, 2009)'
_computing_cell_refinement       'X-Area (Stoe & Cie, 2009)'
_computing_data_reduction        'X-RED32(Stoe & Cie, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2012)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0842P)²+0.2150P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8938
_refine_ls_number_parameters     612
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0754
_refine_ls_R_factor_gt           0.0476
_refine_ls_wR_factor_ref         0.1399
_refine_ls_wR_factor_gt          0.1268
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4908(4) 0.5640(3) 0.4204(2) 0.0468(9) Uani 1 1 d . . . . .
C2 C 0.3774(5) 0.4930(4) 0.4122(3) 0.0622(13) Uani 1 1 d . . . . .
H2 H 0.3764 0.4306 0.3812 0.075 Uiso 1 1 calc R U . . .
C3 C 0.2643(5) 0.5120(4) 0.4493(3) 0.0643(13) Uani 1 1 d . . . . .
H3 H 0.1866 0.4625 0.4441 0.077 Uiso 1 1 calc R U . . .
C4 C 0.2656(5) 0.6029(3) 0.4935(2) 0.0530(10) Uani 1 1 d . . . . .
C5 C 0.3764(5) 0.6741(4) 0.5013(2) 0.0584(12) Uani 1 1 d . . . . .
H5 H 0.3761 0.7369 0.5319 0.070 Uiso 1 1 calc R U . . .
C6 C 0.4886(5) 0.6555(3) 0.4651(2) 0.0557(11) Uani 1 1 d . . . . .
H6 H 0.5656 0.7057 0.4707 0.067 Uiso 1 1 calc R U . . .
C7 C 0.6541(4) 0.4785(3) 0.3417(2) 0.0439(9) Uani 1 1 d . . . . .
C8 C 0.9831(5) 0.5989(3) 0.3353(2) 0.0493(10) Uani 1 1 d . . . . .
H8 H 1.0197 0.5427 0.3085 0.059 Uiso 1 1 calc R U . . .
C9 C 1.0722(4) 0.6939(3) 0.3598(2) 0.0468(9) Uani 1 1 d . . . . .
C10 C 1.0294(5) 0.7685(3) 0.4068(2) 0.0510(10) Uani 1 1 d . . . . .
H9 H 0.9408 0.7583 0.4229 0.061 Uiso 1 1 calc R U . . .
C11 C 1.1123(5) 0.8595(3) 0.4320(2) 0.0584(12) Uani 1 1 d . . . . .
H10 H 1.0788 0.9111 0.4636 0.070 Uiso 1 1 calc R U . . .
C12 C 1.2416(5) 0.8740(4) 0.4110(2) 0.0601(12) Uani 1 1 d . . . . .
H11 H 1.2978 0.9359 0.4284 0.072 Uiso 1 1 calc R U . . .
C13 C 1.2926(5) 0.7988(3) 0.3639(2) 0.0516(10) Uani 1 1 d . . . . .
C14 C 1.4280(5) 0.8116(4) 0.3429(3) 0.0648(13) Uani 1 1 d . . . . .
H14 H 1.4860 0.8719 0.3621 0.078 Uiso 1 1 calc R U . . .
C15 C 1.4775(6) 0.7409(4) 0.2965(3) 0.0684(13) Uani 1 1 d . . . . .
H15 H 1.5686 0.7512 0.2832 0.082 Uiso 1 1 calc R U . . .
C16 C 1.3913(6) 0.6520(4) 0.2683(3) 0.0693(14) Uani 1 1 d . . . . .
H16 H 1.4244 0.6026 0.2351 0.083 Uiso 1 1 calc R U . . .
C17 C 1.2608(5) 0.6351(4) 0.2878(2) 0.0586(12) Uani 1 1 d . . . . .
H17 H 1.2054 0.5738 0.2682 0.070 Uiso 1 1 calc R U . . .
C18 C 1.2073(5) 0.7071(3) 0.3365(2) 0.0485(10) Uani 1 1 d . . . . .
C19 C 0.6830(4) 0.0352(3) 0.13484(19) 0.0415(9) Uani 1 1 d . . . . .
C20 C 0.5960(5) -0.0332(3) 0.0864(2) 0.0509(10) Uani 1 1 d . . . . .
H20 H 0.4995 -0.0434 0.0915 0.061 Uiso 1 1 calc R U . . .
C21 C 0.6516(6) -0.0859(4) 0.0309(2) 0.0606(12) Uani 1 1 d . . . . .
H21 H 0.5918 -0.1305 -0.0024 0.073 Uiso 1 1 calc R U . . .
C22 C 0.7909(6) -0.0746(4) 0.0236(2) 0.0599(12) Uani 1 1 d . . . . .
H22 H 0.8276 -0.1123 -0.0141 0.072 Uiso 1 1 calc R U . . .
C23 C 0.8773(5) -0.0090(4) 0.0706(2) 0.0594(12) Uani 1 1 d . . . . .
H23 H 0.9743 -0.0015 0.0658 0.071 Uiso 1 1 calc R U . . .
C24 C 0.8232(5) 0.0469(3) 0.1255(2) 0.0502(10) Uani 1 1 d . . . . .
H24 H 0.8835 0.0940 0.1571 0.060 Uiso 1 1 calc R U . . .
C25 C 0.6920(4) 0.0552(3) 0.2765(2) 0.0427(9) Uani 1 1 d . . . . .
C26 C 0.7541(5) -0.0387(3) 0.2692(2) 0.0497(10) Uani 1 1 d . . . . .
H26 H 0.7705 -0.0720 0.2258 0.060 Uiso 1 1 calc R U . . .
C27 C 0.7918(5) -0.0840(3) 0.3240(2) 0.0569(11) Uani 1 1 d . . . . .
H27 H 0.8363 -0.1468 0.3181 0.068 Uiso 1 1 calc R U . . .
C28 C 0.7655(5) -0.0385(4) 0.3870(2) 0.0596(12) Uani 1 1 d . . . . .
H28 H 0.7890 -0.0708 0.4245 0.071 Uiso 1 1 calc R U . . .
C29 C 0.7051(6) 0.0538(4) 0.3953(2) 0.0634(13) Uani 1 1 d . . . . .
H29 H 0.6871 0.0855 0.4388 0.076 Uiso 1 1 calc R U . . .
C30 C 0.6701(5) 0.1014(3) 0.3408(2) 0.0545(11) Uani 1 1 d . . . . .
H30 H 0.6308 0.1663 0.3475 0.065 Uiso 1 1 calc R U . . .
C31 C 0.4373(4) 0.0702(3) 0.20368(19) 0.0402(8) Uani 1 1 d . . . . .
C32 C 0.3935(5) -0.0232(3) 0.2227(2) 0.0486(10) Uani 1 1 d . . . . .
H32 H 0.4605 -0.0679 0.2355 0.058 Uiso 1 1 calc R U . . .
C33 C 0.2526(5) -0.0507(4) 0.2229(2) 0.0549(11) Uani 1 1 d . . . . .
H33 H 0.2234 -0.1141 0.2361 0.066 Uiso 1 1 calc R U . . .
C34 C 0.1553(5) 0.0132(4) 0.2041(2) 0.0593(12) Uani 1 1 d . . . . .
H34 H 0.0590 -0.0053 0.2052 0.071 Uiso 1 1 calc R U . . .
C35 C 0.1973(5) 0.1053(4) 0.1833(3) 0.0605(12) Uani 1 1 d . . . . .
H35 H 0.1298 0.1487 0.1691 0.073 Uiso 1 1 calc R U . . .
C36 C 0.3373(5) 0.1329(3) 0.1834(2) 0.0505(10) Uani 1 1 d . . . . .
H36 H 0.3658 0.1959 0.1694 0.061 Uiso 1 1 calc R U . . .
C37 C 0.6892(4) 0.3299(3) 0.0475(2) 0.0449(9) Uani 1 1 d . . . . .
C38 C 0.7095(5) 0.2270(3) 0.0281(2) 0.0571(12) Uani 1 1 d . . . . .
H38 H 0.6879 0.1794 0.0570 0.068 Uiso 1 1 calc R U . . .
C39 C 0.7604(6) 0.1912(4) -0.0321(3) 0.0688(14) Uani 1 1 d . . . . .
H39 H 0.7713 0.1196 -0.0448 0.083 Uiso 1 1 calc R U . . .
C40 C 0.7951(6) 0.2591(4) -0.0736(3) 0.0674(14) Uani 1 1 d . . . . .
H40 H 0.8313 0.2349 -0.1148 0.081 Uiso 1 1 calc R U . . .
C41 C 0.7777(7) 0.3613(4) -0.0557(3) 0.0749(16) Uani 1 1 d . . . . .
H41 H 0.8019 0.4082 -0.0846 0.090 Uiso 1 1 calc R U . . .
C42 C 0.7251(6) 0.3973(4) 0.0040(3) 0.0682(14) Uani 1 1 d . . . . .
H42 H 0.7132 0.4689 0.0158 0.082 Uiso 1 1 calc R U . . .
C43 C 0.4348(5) 0.3752(3) 0.1061(2) 0.0451(9) Uani 1 1 d . . . . .
C44 C 0.3713(5) 0.3527(3) 0.0413(2) 0.0525(11) Uani 1 1 d . . . . .
H44 H 0.4271 0.3416 0.0048 0.063 Uiso 1 1 calc R U . . .
C45 C 0.2268(5) 0.3461(4) 0.0289(3) 0.0618(12) Uani 1 1 d . . . . .
H45 H 0.1851 0.3305 -0.0159 0.074 Uiso 1 1 calc R U . . .
C46 C 0.1439(5) 0.3621(3) 0.0808(3) 0.0591(12) Uani 1 1 d . . . . .
H46 H 0.0453 0.3568 0.0723 0.071 Uiso 1 1 calc R U . . .
C47 C 0.2058(5) 0.3862(3) 0.1459(3) 0.0591(12) Uani 1 1 d . . . . .
H47 H 0.1496 0.3979 0.1822 0.071 Uiso 1 1 calc R U . . .
C48 C 0.3486(5) 0.3931(3) 0.1581(2) 0.0507(10) Uani 1 1 d . . . . .
H48 H 0.3896 0.4105 0.2029 0.061 Uiso 1 1 calc R U . . .
C49 C 0.6871(5) 0.5095(3) 0.1434(2) 0.0477(10) Uani 1 1 d . . . . .
C50 C 0.6060(5) 0.5903(3) 0.1336(2) 0.0555(11) Uani 1 1 d . . . . .
H50 H 0.5091 0.5770 0.1204 0.067 Uiso 1 1 calc R U . . .
C51 C 0.6677(7) 0.6913(3) 0.1434(3) 0.0716(16) Uani 1 1 d . . . . .
H51 H 0.6122 0.7467 0.1372 0.086 Uiso 1 1 calc R U . . .
C52 C 0.8079(7) 0.7108(4) 0.1620(3) 0.0706(15) Uani 1 1 d . . . . .
H52 H 0.8492 0.7795 0.1680 0.085 Uiso 1 1 calc R U . . .
C53 C 0.8885(6) 0.6316(4) 0.1720(3) 0.0667(14) Uani 1 1 d . . . . .
H53 H 0.9854 0.6456 0.1848 0.080 Uiso 1 1 calc R U . . .
C54 C 0.8294(5) 0.5310(3) 0.1633(2) 0.0568(11) Uani 1 1 d . . . . .
H54 H 0.8856 0.4765 0.1710 0.068 Uiso 1 1 calc R U . . .
C55 C 0.3149(8) 0.1865(6) 0.3673(4) 0.115(3) Uani 1 1 d . . . . .
H55A H 0.4031 0.2248 0.3865 0.172 Uiso 1 1 calc R U . . .
H55B H 0.2870 0.2066 0.3241 0.172 Uiso 1 1 calc R U . . .
H55C H 0.3267 0.1122 0.3608 0.172 Uiso 1 1 calc R U . . .
C56 C 0.0502(7) 0.1383(6) 0.3743(4) 0.101(2) Uani 1 1 d . . . . .
H56A H 0.0781 0.0676 0.3635 0.151 Uiso 1 1 calc R U . . .
H56B H 0.0285 0.1654 0.3329 0.151 Uiso 1 1 calc R U . . .
H56C H -0.0323 0.1382 0.3993 0.151 Uiso 1 1 calc R U . . .
Br1 Br 0.11202(6) 0.63044(4) 0.54436(3) 0.06890(17) Uani 1 1 d . . . . .
Cl1 Cl 0.92056(11) 0.30743(8) 0.24128(6) 0.0544(3) Uani 1 1 d . . . . .
Cu1 Cu 0.67570(5) 0.28559(3) 0.21393(2) 0.04147(14) Uani 1 1 d . . . . .
N1 N 0.6126(4) 0.5535(3) 0.38703(19) 0.0503(9) Uani 1 1 d . . . . .
N2 N 0.7832(4) 0.4990(3) 0.32258(18) 0.0480(8) Uani 1 1 d . . . . .
N3 N 0.8572(4) 0.5906(3) 0.34934(18) 0.0498(8) Uani 1 1 d . . . . .
O1 O 0.2212(5) 0.1664(4) 0.4802(2) 0.1101(16) Uani 1 1 d . . . . .
P1 P 0.62087(11) 0.11321(7) 0.20667(5) 0.0386(2) Uani 1 1 d . . . . .
P2 P 0.62209(11) 0.37349(7) 0.12766(5) 0.0426(2) Uani 1 1 d . . . . .
S1 S 0.56593(11) 0.36547(8) 0.30785(5) 0.0472(3) Uani 1 1 d . . . . .
S2 S 0.18469(16) 0.21521(12) 0.42231(8) 0.0763(4) Uani 1 1 d . . . . .
H1 H 0.681(7) 0.602(5) 0.399(3) 0.092 Uiso 1 1 d . U . . .
H2A H 0.827(6) 0.442(5) 0.300(3) 0.092 Uiso 1 1 d . U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.376(6) . ?
C1 C6 1.389(6) . ?
C1 N1 1.409(5) . ?
C2 C3 1.391(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.373(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.360(7) . ?
C4 Br1 1.897(5) . ?
C5 C6 1.372(6) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 N1 1.342(5) . ?
C7 N2 1.359(5) . ?
C7 S1 1.681(4) . ?
C8 N3 1.274(5) . ?
C8 C9 1.465(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.364(6) . ?
C9 C18 1.434(6) . ?
C10 C11 1.397(6) . ?
C10 H9 0.9500 . ?
C11 C12 1.365(7) . ?
C11 H10 0.9500 . ?
C12 C13 1.404(7) . ?
C12 H11 0.9500 . ?
C13 C14 1.418(7) . ?
C13 C18 1.424(6) . ?
C14 C15 1.353(7) . ?
C14 H14 0.9500 . ?
C15 C16 1.405(7) . ?
C15 H15 0.9500 . ?
C16 C17 1.368(7) . ?
C16 H16 0.9500 . ?
C17 C18 1.410(6) . ?
C17 H17 0.9500 . ?
C19 C24 1.385(6) . ?
C19 C20 1.403(6) . ?
C19 P1 1.812(4) . ?
C20 C21 1.392(6) . ?
C20 H20 0.9500 . ?
C21 C22 1.368(7) . ?
C21 H21 0.9500 . ?
C22 C23 1.368(7) . ?
C22 H22 0.9500 . ?
C23 C24 1.392(6) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C25 C30 1.389(6) . ?
C25 C26 1.399(6) . ?
C25 P1 1.824(4) . ?
C26 C27 1.379(6) . ?
C26 H26 0.9500 . ?
C27 C28 1.374(7) . ?
C27 H27 0.9500 . ?
C28 C29 1.372(7) . ?
C28 H28 0.9500 . ?
C29 C30 1.388(7) . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?
C31 C36 1.388(6) . ?
C31 C32 1.398(5) . ?
C31 P1 1.821(4) . ?
C32 C33 1.387(6) . ?
C32 H32 0.9500 . ?
C33 C34 1.372(7) . ?
C33 H33 0.9500 . ?
C34 C35 1.393(7) . ?
C34 H34 0.9500 . ?
C35 C36 1.379(6) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C37 C38 1.379(6) . ?
C37 C42 1.397(6) . ?
C37 P2 1.824(4) . ?
C38 C39 1.380(6) . ?
C38 H38 0.9500 . ?
C39 C40 1.369(7) . ?
C39 H39 0.9500 . ?
C40 C41 1.358(7) . ?
C40 H40 0.9500 . ?
C41 C42 1.380(7) . ?
C41 H41 0.9500 . ?
C42 H42 0.9500 . ?
C43 C44 1.386(6) . ?
C43 C48 1.399(6) . ?
C43 P2 1.829(4) . ?
C44 C45 1.393(7) . ?
C44 H44 0.9500 . ?
C45 C46 1.375(7) . ?
C45 H45 0.9500 . ?
C46 C47 1.386(7) . ?
C46 H46 0.9500 . ?
C47 C48 1.376(7) . ?
C47 H47 0.9500 . ?
C48 H48 0.9500 . ?
C49 C50 1.388(6) . ?
C49 C54 1.399(7) . ?
C49 P2 1.828(4) . ?
C50 C51 1.399(7) . ?
C50 H50 0.9500 . ?
C51 C52 1.373(8) . ?
C51 H51 0.9500 . ?
C52 C53 1.371(8) . ?
C52 H52 0.9500 . ?
C53 C54 1.386(6) . ?
C53 H53 0.9500 . ?
C54 H54 0.9500 . ?
C55 S2 1.769(6) . ?
C55 H55A 0.9800 . ?
C55 H55B 0.9800 . ?
C55 H55C 0.9800 . ?
C56 S2 1.724(7) . ?
C56 H56A 0.9800 . ?
C56 H56B 0.9800 . ?
C56 H56C 0.9800 . ?
Cl1 Cu1 2.3740(12) . ?
Cu1 P1 2.2744(10) . ?
Cu1 P2 2.2949(12) . ?
Cu1 S1 2.3873(11) . ?
N1 H1 0.88(6) . ?
N2 N3 1.370(5) . ?
N2 H2A 0.96(6) . ?
O1 S2 1.458(5) . ?

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
C2 C1 C6 118.8(4) . . ?
C2 C1 N1 126.0(4) . . ?
C6 C1 N1 115.2(4) . . ?
C1 C2 C3 120.3(4) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C4 C3 C2 119.6(4) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C5 C4 C3 120.6(4) . . ?
C5 C4 Br1 119.2(3) . . ?
C3 C4 Br1 120.2(4) . . ?
C4 C5 C6 120.0(4) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C1 120.7(4) . . ?
C5 C6 H6 119.7 . . ?
C1 C6 H6 119.7 . . ?
N1 C7 N2 114.2(3) . . ?
N1 C7 S1 127.4(3) . . ?
N2 C7 S1 118.4(3) . . ?
N3 C8 C9 120.9(4) . . ?
N3 C8 H8 119.5 . . ?
C9 C8 H8 119.5 . . ?
C10 C9 C18 119.7(4) . . ?
C10 C9 C8 120.2(4) . . ?
C18 C9 C8 120.1(4) . . ?
C9 C10 C11 121.7(4) . . ?
C9 C10 H9 119.1 . . ?
C11 C10 H9 119.1 . . ?
C12 C11 C10 119.9(4) . . ?
C12 C11 H10 120.0 . . ?
C10 C11 H10 120.0 . . ?
C11 C12 C13 120.8(4) . . ?
C11 C12 H11 119.6 . . ?
C13 C12 H11 119.6 . . ?
C12 C13 C14 121.5(4) . . ?
C12 C13 C18 119.7(4) . . ?
C14 C13 C18 118.9(4) . . ?
C15 C14 C13 122.2(5) . . ?
C15 C14 H14 118.9 . . ?
C13 C14 H14 118.9 . . ?
C14 C15 C16 118.6(5) . . ?
C14 C15 H15 120.7 . . ?
C16 C15 H15 120.7 . . ?
C17 C16 C15 121.5(5) . . ?
C17 C16 H16 119.3 . . ?
C15 C16 H16 119.3 . . ?
C16 C17 C18 121.0(4) . . ?
C16 C17 H17 119.5 . . ?
C18 C17 H17 119.5 . . ?
C17 C18 C13 117.8(4) . . ?
C17 C18 C9 124.1(4) . . ?
C13 C18 C9 118.1(4) . . ?
C24 C19 C20 118.0(4) . . ?
C24 C19 P1 118.3(3) . . ?
C20 C19 P1 123.6(3) . . ?
C21 C20 C19 119.7(4) . . ?
C21 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
C22 C21 C20 121.1(4) . . ?
C22 C21 H21 119.4 . . ?
C20 C21 H21 119.4 . . ?
C21 C22 C23 119.8(4) . . ?
C21 C22 H22 120.1 . . ?
C23 C22 H22 120.1 . . ?
C22 C23 C24 120.0(5) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
C19 C24 C23 121.3(4) . . ?
C19 C24 H24 119.4 . . ?
C23 C24 H24 119.4 . . ?
C30 C25 C26 117.6(4) . . ?
C30 C25 P1 117.9(3) . . ?
C26 C25 P1 124.1(3) . . ?
C27 C26 C25 121.1(4) . . ?
C27 C26 H26 119.4 . . ?
C25 C26 H26 119.4 . . ?
C28 C27 C26 120.3(4) . . ?
C28 C27 H27 119.8 . . ?
C26 C27 H27 119.8 . . ?
C29 C28 C27 119.5(4) . . ?
C29 C28 H28 120.2 . . ?
C27 C28 H28 120.2 . . ?
C28 C29 C30 120.7(4) . . ?
C28 C29 H29 119.7 . . ?
C30 C29 H29 119.7 . . ?
C29 C30 C25 120.7(4) . . ?
C29 C30 H30 119.7 . . ?
C25 C30 H30 119.7 . . ?
C36 C31 C32 118.8(4) . . ?
C36 C31 P1 119.2(3) . . ?
C32 C31 P1 122.0(3) . . ?
C33 C32 C31 120.2(4) . . ?
C33 C32 H32 119.9 . . ?
C31 C32 H32 119.9 . . ?
C34 C33 C32 120.3(4) . . ?
C34 C33 H33 119.9 . . ?
C32 C33 H33 119.9 . . ?
C33 C34 C35 120.2(4) . . ?
C33 C34 H34 119.9 . . ?
C35 C34 H34 119.9 . . ?
C36 C35 C34 119.6(4) . . ?
C36 C35 H35 120.2 . . ?
C34 C35 H35 120.2 . . ?
C35 C36 C31 121.0(4) . . ?
C35 C36 H36 119.5 . . ?
C31 C36 H36 119.5 . . ?
C38 C37 C42 117.1(4) . . ?
C38 C37 P2 120.1(3) . . ?
C42 C37 P2 122.8(3) . . ?
C37 C38 C39 121.7(4) . . ?
C37 C38 H38 119.1 . . ?
C39 C38 H38 119.1 . . ?
C40 C39 C38 119.8(4) . . ?
C40 C39 H39 120.1 . . ?
C38 C39 H39 120.1 . . ?
C41 C40 C39 120.0(4) . . ?
C41 C40 H40 120.0 . . ?
C39 C40 H40 120.0 . . ?
C40 C41 C42 120.5(5) . . ?
C40 C41 H41 119.8 . . ?
C42 C41 H41 119.8 . . ?
C41 C42 C37 120.9(4) . . ?
C41 C42 H42 119.5 . . ?
C37 C42 H42 119.5 . . ?
C44 C43 C48 117.5(4) . . ?
C44 C43 P2 124.0(3) . . ?
C48 C43 P2 118.3(3) . . ?
C43 C44 C45 120.9(4) . . ?
C43 C44 H44 119.5 . . ?
C45 C44 H44 119.5 . . ?
C46 C45 C44 120.6(5) . . ?
C46 C45 H45 119.7 . . ?
C44 C45 H45 119.7 . . ?
C45 C46 C47 119.2(5) . . ?
C45 C46 H46 120.4 . . ?
C47 C46 H46 120.4 . . ?
C48 C47 C46 120.2(4) . . ?
C48 C47 H47 119.9 . . ?
C46 C47 H47 119.9 . . ?
C47 C48 C43 121.6(4) . . ?
C47 C48 H48 119.2 . . ?
C43 C48 H48 119.2 . . ?
C50 C49 C54 119.2(4) . . ?
C50 C49 P2 124.1(4) . . ?
C54 C49 P2 116.6(3) . . ?
C49 C50 C51 119.7(5) . . ?
C49 C50 H50 120.2 . . ?
C51 C50 H50 120.2 . . ?
C52 C51 C50 120.4(5) . . ?
C52 C51 H51 119.8 . . ?
C50 C51 H51 119.8 . . ?
C53 C52 C51 120.3(5) . . ?
C53 C52 H52 119.9 . . ?
C51 C52 H52 119.9 . . ?
C52 C53 C54 120.4(5) . . ?
C52 C53 H53 119.8 . . ?
C54 C53 H53 119.8 . . ?
C53 C54 C49 120.1(5) . . ?
C53 C54 H54 120.0 . . ?
C49 C54 H54 120.0 . . ?
S2 C55 H55A 109.5 . . ?
S2 C55 H55B 109.5 . . ?
H55A C55 H55B 109.5 . . ?
S2 C55 H55C 109.5 . . ?
H55A C55 H55C 109.5 . . ?
H55B C55 H55C 109.5 . . ?
S2 C56 H56A 109.5 . . ?
S2 C56 H56B 109.5 . . ?
H56A C56 H56B 109.5 . . ?
S2 C56 H56C 109.5 . . ?
H56A C56 H56C 109.5 . . ?
H56B C56 H56C 109.5 . . ?
P1 Cu1 P2 122.72(4) . . ?
P1 Cu1 Cl1 104.80(4) . . ?
P2 Cu1 Cl1 108.06(4) . . ?
P1 Cu1 S1 105.19(4) . . ?
P2 Cu1 S1 107.07(4) . . ?
Cl1 Cu1 S1 108.35(4) . . ?
C7 N1 C1 133.1(4) . . ?
C7 N1 H1 109(4) . . ?
C1 N1 H1 118(4) . . ?
C7 N2 N3 119.5(3) . . ?
C7 N2 H2A 117(4) . . ?
N3 N2 H2A 122(4) . . ?
C8 N3 N2 115.7(4) . . ?
C19 P1 C31 104.76(18) . . ?
C19 P1 C25 102.94(18) . . ?
C31 P1 C25 100.43(18) . . ?
C19 P1 Cu1 113.74(13) . . ?
C31 P1 Cu1 117.34(13) . . ?
C25 P1 Cu1 115.71(13) . . ?
C37 P2 C49 100.74(18) . . ?
C37 P2 C43 103.67(19) . . ?
C49 P2 C43 104.55(19) . . ?
C37 P2 Cu1 118.01(14) . . ?
C49 P2 Cu1 114.60(15) . . ?
C43 P2 Cu1 113.52(13) . . ?
C7 S1 Cu1 109.90(14) . . ?
O1 S2 C56 107.2(3) . . ?
O1 S2 C55 105.9(4) . . ?
C56 S2 C55 97.0(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
C6 C1 C2 C3 -1.3(8) . . . . ?
N1 C1 C2 C3 178.8(5) . . . . ?
C1 C2 C3 C4 0.8(8) . . . . ?
C2 C3 C4 C5 0.0(8) . . . . ?
C2 C3 C4 Br1 179.8(4) . . . . ?
C3 C4 C5 C6 -0.3(7) . . . . ?
Br1 C4 C5 C6 179.8(4) . . . . ?
C4 C5 C6 C1 -0.2(7) . . . . ?
C2 C1 C6 C5 1.0(7) . . . . ?
N1 C1 C6 C5 -179.1(4) . . . . ?
N3 C8 C9 C10 10.6(7) . . . . ?
N3 C8 C9 C18 -171.8(4) . . . . ?
C18 C9 C10 C11 1.7(7) . . . . ?
C8 C9 C10 C11 179.2(4) . . . . ?
C9 C10 C11 C12 -2.0(7) . . . . ?
C10 C11 C12 C13 0.4(7) . . . . ?
C11 C12 C13 C14 -178.3(5) . . . . ?
C11 C12 C13 C18 1.5(7) . . . . ?
C12 C13 C14 C15 -178.4(5) . . . . ?
C18 C13 C14 C15 1.7(7) . . . . ?
C13 C14 C15 C16 0.0(8) . . . . ?
C14 C15 C16 C17 -1.2(9) . . . . ?
C15 C16 C17 C18 0.7(9) . . . . ?
C16 C17 C18 C13 1.0(7) . . . . ?
C16 C17 C18 C9 -179.3(5) . . . . ?
C12 C13 C18 C17 178.0(4) . . . . ?
C14 C13 C18 C17 -2.2(7) . . . . ?
C12 C13 C18 C9 -1.8(6) . . . . ?
C14 C13 C18 C9 178.1(4) . . . . ?
C10 C9 C18 C17 -179.5(4) . . . . ?
C8 C9 C18 C17 2.9(7) . . . . ?
C10 C9 C18 C13 0.2(6) . . . . ?
C8 C9 C18 C13 -177.4(4) . . . . ?
C24 C19 C20 C21 -0.5(6) . . . . ?
P1 C19 C20 C21 176.5(3) . . . . ?
C19 C20 C21 C22 1.9(7) . . . . ?
C20 C21 C22 C23 -1.4(8) . . . . ?
C21 C22 C23 C24 -0.6(8) . . . . ?
C20 C19 C24 C23 -1.5(6) . . . . ?
P1 C19 C24 C23 -178.6(4) . . . . ?
C22 C23 C24 C19 2.1(7) . . . . ?
C30 C25 C26 C27 0.2(6) . . . . ?
P1 C25 C26 C27 -172.7(4) . . . . ?
C25 C26 C27 C28 1.8(7) . . . . ?
C26 C27 C28 C29 -1.9(8) . . . . ?
C27 C28 C29 C30 0.2(8) . . . . ?
C28 C29 C30 C25 1.8(8) . . . . ?
C26 C25 C30 C29 -1.9(7) . . . . ?
P1 C25 C30 C29 171.4(4) . . . . ?
C36 C31 C32 C33 -1.7(6) . . . . ?
P1 C31 C32 C33 176.8(3) . . . . ?
C31 C32 C33 C34 0.4(7) . . . . ?
C32 C33 C34 C35 1.3(7) . . . . ?
C33 C34 C35 C36 -1.7(8) . . . . ?
C34 C35 C36 C31 0.3(7) . . . . ?
C32 C31 C36 C35 1.4(6) . . . . ?
P1 C31 C36 C35 -177.1(4) . . . . ?
C42 C37 C38 C39 -1.3(8) . . . . ?
P2 C37 C38 C39 -179.9(4) . . . . ?
C37 C38 C39 C40 1.5(9) . . . . ?
C38 C39 C40 C41 -0.8(9) . . . . ?
C39 C40 C41 C42 0.0(10) . . . . ?
C40 C41 C42 C37 0.2(10) . . . . ?
C38 C37 C42 C41 0.4(8) . . . . ?
P2 C37 C42 C41 178.9(5) . . . . ?
C48 C43 C44 C45 -1.3(6) . . . . ?
P2 C43 C44 C45 174.0(3) . . . . ?
C43 C44 C45 C46 0.1(7) . . . . ?
C44 C45 C46 C47 0.8(7) . . . . ?
C45 C46 C47 C48 -0.5(7) . . . . ?
C46 C47 C48 C43 -0.8(7) . . . . ?
C44 C43 C48 C47 1.6(6) . . . . ?
P2 C43 C48 C47 -174.0(3) . . . . ?
C54 C49 C50 C51 0.4(6) . . . . ?
P2 C49 C50 C51 -176.2(3) . . . . ?
C49 C50 C51 C52 0.6(7) . . . . ?
C50 C51 C52 C53 -0.8(8) . . . . ?
C51 C52 C53 C54 0.0(8) . . . . ?
C52 C53 C54 C49 1.0(7) . . . . ?
C50 C49 C54 C53 -1.2(7) . . . . ?
P2 C49 C54 C53 175.7(4) . . . . ?
N2 C7 N1 C1 -179.1(4) . . . . ?
S1 C7 N1 C1 0.4(8) . . . . ?
C2 C1 N1 C7 -0.6(8) . . . . ?
C6 C1 N1 C7 179.5(5) . . . . ?
N1 C7 N2 N3 -0.5(6) . . . . ?
S1 C7 N2 N3 179.9(3) . . . . ?
C9 C8 N3 N2 178.8(4) . . . . ?
C7 N2 N3 C8 171.8(4) . . . . ?
C24 C19 P1 C31 -176.9(3) . . . . ?
C20 C19 P1 C31 6.1(4) . . . . ?
C24 C19 P1 C25 -72.2(4) . . . . ?
C20 C19 P1 C25 110.8(4) . . . . ?
C24 C19 P1 Cu1 53.7(4) . . . . ?
C20 C19 P1 Cu1 -123.3(3) . . . . ?
C36 C31 P1 C19 -105.7(3) . . . . ?
C32 C31 P1 C19 75.9(4) . . . . ?
C36 C31 P1 C25 147.8(3) . . . . ?
C32 C31 P1 C25 -30.6(4) . . . . ?
C36 C31 P1 Cu1 21.6(4) . . . . ?
C32 C31 P1 Cu1 -156.9(3) . . . . ?
C30 C25 P1 C19 176.3(3) . . . . ?
C26 C25 P1 C19 -10.8(4) . . . . ?
C30 C25 P1 C31 -75.8(4) . . . . ?
C26 C25 P1 C31 97.1(4) . . . . ?
C30 C25 P1 Cu1 51.6(4) . . . . ?
C26 C25 P1 Cu1 -135.5(3) . . . . ?
C38 C37 P2 C49 156.2(4) . . . . ?
C42 C37 P2 C49 -22.3(5) . . . . ?
C38 C37 P2 C43 -95.8(4) . . . . ?
C42 C37 P2 C43 85.7(4) . . . . ?
C38 C37 P2 Cu1 30.7(4) . . . . ?
C42 C37 P2 Cu1 -147.8(4) . . . . ?
C50 C49 P2 C37 102.1(4) . . . . ?
C54 C49 P2 C37 -74.7(4) . . . . ?
C50 C49 P2 C43 -5.2(4) . . . . ?
C54 C49 P2 C43 178.0(3) . . . . ?
C50 C49 P2 Cu1 -130.1(3) . . . . ?
C54 C49 P2 Cu1 53.1(4) . . . . ?
C44 C43 P2 C37 -3.2(4) . . . . ?
C48 C43 P2 C37 172.1(3) . . . . ?
C44 C43 P2 C49 102.0(4) . . . . ?
C48 C43 P2 C49 -82.8(3) . . . . ?
C44 C43 P2 Cu1 -132.5(3) . . . . ?
C48 C43 P2 Cu1 42.8(3) . . . . ?
N1 C7 S1 Cu1 167.4(4) . . . . ?
N2 C7 S1 Cu1 -13.1(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2A Cl1 0.96(6) 2.25(6) 3.206(4) 176(5) .
N1 H1 N3 0.88(6) 2.05(6) 2.585(5) 119(5) .

_refine_diff_density_max         0.823
_refine_diff_density_min         -0.871
_refine_diff_density_rms         0.072

_symmetry_cell_setting           ?
_symmetry_space_group_name_h-m   ?
_symmetry_int_tables_number      ?
_chemical_absolute_configuration ?

####################################################################### 
# 
# 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_sb27
_database_code_depnum_ccdc_archive 'CCDC 1002349'
_audit_update_record             
;
2015-01-30 deposited with the CCDC.
2015-02-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        SB-27
_chemical_name_common            ?
_chemical_formula_moiety         'C54 H44 Br Cl Cu N3 P2 S, C2 H3 N'
_chemical_formula_sum            'C56 H47 Br Cl Cu N4 P2 S'
_exptl_crystal_recrystallization_method dichloromethane
_chemical_melting_point          ?

_exptl_crystal_description       block
_exptl_crystal_colour            yellow

_diffrn_ambient_temperature      200(2)
_chemical_formula_weight         1048.88

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_int_tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_chemical_absolute_configuration .

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.4984(4)
_cell_length_b                   13.1221(5)
_cell_length_c                   20.6583(9)
_cell_angle_alpha                100.185(3)
_cell_angle_beta                 95.359(3)
_cell_angle_gamma                96.502(3)
_cell_volume                     2500.96(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    33934
_cell_measurement_theta_min      1.59
_cell_measurement_theta_max      25.67
_exptl_crystal_size_max          0.530
_exptl_crystal_size_mid          0.310
_exptl_crystal_size_min          0.200
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1076
_exptl_absorpt_coefficient_mu    1.436
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.8576
_exptl_absorpt_correction_T_max  0.9460
_exptl_absorpt_process_details   
;
Stoe & Cie (2002). X-SHAPE. Stoe & Cie, Darmstadt, Germany
;
_exptl_special_details           
;
 ?
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean 6.67
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            48158
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.591
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             8790
_reflns_number_gt                7633
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'X-Area (Stoe & Cie, 2009)'
_computing_cell_refinement       'X-Area (Stoe & Cie, 2009)'
_computing_data_reduction        'X-RED32(Stoe & Cie, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2012)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0458P)²+0.9563P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8790
_refine_ls_number_parameters     596
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0300
_refine_ls_wR_factor_ref         0.0811
_refine_ls_wR_factor_gt          0.0784
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.0045(2) 0.56237(17) 0.42204(10) 0.0408(5) Uani 1 1 d . . . . .
C2 C -0.1261(3) 0.48997(19) 0.41051(13) 0.0535(6) Uani 1 1 d . . . . .
H2 H -0.1309 0.4290 0.3792 0.064 Uiso 1 1 calc R U . . .
C3 C -0.2405(3) 0.5084(2) 0.44561(13) 0.0554(6) Uani 1 1 d . . . . .
H3 H -0.3221 0.4596 0.4378 0.066 Uiso 1 1 calc R U . . .
C4 C -0.2344(3) 0.59823(19) 0.49202(11) 0.0453(5) Uani 1 1 d . . . . .
C5 C -0.1149(3) 0.6711(2) 0.50376(12) 0.0514(6) Uani 1 1 d . . . . .
H5 H -0.1109 0.7320 0.5351 0.062 Uiso 1 1 calc R U . . .
C6 C -0.0005(3) 0.65322(19) 0.46861(11) 0.0482(5) Uani 1 1 d . . . . .
H6 H 0.0804 0.7028 0.4763 0.058 Uiso 1 1 calc R U . . .
C7 C 0.1586(2) 0.48121(17) 0.34360(10) 0.0381(4) Uani 1 1 d . . . . .
C8 C 0.4987(2) 0.60665(17) 0.33654(11) 0.0422(5) Uani 1 1 d . . . . .
H8 H 0.5275 0.5507 0.3090 0.051 Uiso 1 1 calc R U . . .
C9 C 0.5995(2) 0.70106(17) 0.36012(10) 0.0405(5) Uani 1 1 d . . . . .
C10 C 0.5627(3) 0.78229(18) 0.40446(11) 0.0459(5) Uani 1 1 d . . . . .
H10 H 0.4725 0.7769 0.4186 0.055 Uiso 1 1 calc R U . . .
C11 C 0.6593(3) 0.87306(19) 0.42856(12) 0.0503(6) Uani 1 1 d . . . . .
H11 H 0.6322 0.9276 0.4580 0.060 Uiso 1 1 calc R U . . .
C12 C 0.7922(3) 0.88181(19) 0.40913(12) 0.0519(6) Uani 1 1 d . . . . .
H12 H 0.8555 0.9421 0.4260 0.062 Uiso 1 1 calc R U . . .
C13 C 0.8360(3) 0.80158(18) 0.36408(11) 0.0448(5) Uani 1 1 d . . . . .
C14 C 0.9744(3) 0.8100(2) 0.34405(13) 0.0540(6) Uani 1 1 d . . . . .
H14 H 1.0389 0.8693 0.3618 0.065 Uiso 1 1 calc R U . . .
C15 C 1.0153(3) 0.7334(2) 0.29942(14) 0.0589(6) Uani 1 1 d . . . . .
H15 H 1.1071 0.7400 0.2871 0.071 Uiso 1 1 calc R U . . .
C16 C 0.9185(3) 0.6442(2) 0.27193(13) 0.0576(6) Uani 1 1 d . . . . .
H16 H 0.9458 0.5925 0.2405 0.069 Uiso 1 1 calc R U . . .
C17 C 0.7848(3) 0.63236(19) 0.29075(12) 0.0498(5) Uani 1 1 d . . . . .
H17 H 0.7229 0.5720 0.2723 0.060 Uiso 1 1 calc R U . . .
C18 C 0.7377(2) 0.70946(17) 0.33761(10) 0.0413(5) Uani 1 1 d . . . . .
C19 C 0.2119(2) 0.06487(16) 0.27613(10) 0.0366(4) Uani 1 1 d . . . . .
C20 C 0.2303(3) 0.12706(19) 0.33834(11) 0.0511(6) Uani 1 1 d . . . . .
H20 H 0.2009 0.1930 0.3441 0.061 Uiso 1 1 calc R U . . .
C21 C 0.2922(3) 0.0922(2) 0.39229(12) 0.0640(7) Uani 1 1 d . . . . .
H21 H 0.3031 0.1346 0.4341 0.077 Uiso 1 1 calc R U . . .
C22 C 0.3378(3) -0.0049(2) 0.38443(12) 0.0540(6) Uani 1 1 d . . . . .
H22 H 0.3780 -0.0287 0.4208 0.065 Uiso 1 1 calc R U . . .
C23 C 0.3232(2) -0.06636(18) 0.32224(11) 0.0457(5) Uani 1 1 d . . . . .
H23 H 0.3566 -0.1309 0.3163 0.055 Uiso 1 1 calc R U . . .
C24 C 0.2593(2) -0.03243(17) 0.26871(11) 0.0413(5) Uani 1 1 d . . . . .
H24 H 0.2478 -0.0752 0.2271 0.050 Uiso 1 1 calc R U . . .
C25 C -0.0646(2) 0.06523(16) 0.20805(10) 0.0371(4) Uani 1 1 d . . . . .
C26 C -0.1107(3) -0.02707(19) 0.22833(13) 0.0510(6) Uani 1 1 d . . . . .
H26 H -0.0441 -0.0683 0.2417 0.061 Uiso 1 1 calc R U . . .
C27 C -0.2542(3) -0.0583(2) 0.22884(13) 0.0561(6) Uani 1 1 d . . . . .
H27 H -0.2838 -0.1200 0.2429 0.067 Uiso 1 1 calc R U . . .
C28 C -0.3532(3) 0.0013(2) 0.20872(14) 0.0583(6) Uani 1 1 d . . . . .
H28 H -0.4499 -0.0198 0.2092 0.070 Uiso 1 1 calc R U . . .
C29 C -0.3095(3) 0.0926(2) 0.18778(16) 0.0625(7) Uani 1 1 d . . . . .
H29 H -0.3767 0.1327 0.1736 0.075 Uiso 1 1 calc R U . . .
C30 C -0.1657(2) 0.12463(19) 0.18775(13) 0.0499(6) Uani 1 1 d . . . . .
H30 H -0.1366 0.1866 0.1740 0.060 Uiso 1 1 calc R U . . .
C31 C 0.1746(2) 0.03169(16) 0.13533(10) 0.0378(4) Uani 1 1 d . . . . .
C32 C 0.3186(2) 0.04090(18) 0.12664(11) 0.0454(5) Uani 1 1 d . . . . .
H32 H 0.3842 0.0854 0.1584 0.055 Uiso 1 1 calc R U . . .
C33 C 0.3658(3) -0.0152(2) 0.07153(12) 0.0541(6) Uani 1 1 d . . . . .
H33 H 0.4627 -0.0095 0.0669 0.065 Uiso 1 1 calc R U . . .
C34 C 0.2689(3) -0.0794(2) 0.02342(12) 0.0564(6) Uani 1 1 d . . . . .
H34 H 0.3002 -0.1169 -0.0139 0.068 Uiso 1 1 calc R U . . .
C35 C 0.1263(3) -0.0880(2) 0.03078(12) 0.0568(6) Uani 1 1 d . . . . .
H35 H 0.0612 -0.1305 -0.0021 0.068 Uiso 1 1 calc R U . . .
C36 C 0.0776(3) -0.03386(18) 0.08685(11) 0.0466(5) Uani 1 1 d . . . . .
H36 H -0.0192 -0.0415 0.0918 0.056 Uiso 1 1 calc R U . . .
C37 C -0.0584(2) 0.37282(16) 0.10340(10) 0.0371(4) Uani 1 1 d . . . . .
C38 C -0.1472(2) 0.38754(18) 0.15345(11) 0.0442(5) Uani 1 1 d . . . . .
H38 H -0.1078 0.4002 0.1975 0.053 Uiso 1 1 calc R U . . .
C39 C -0.2928(3) 0.3835(2) 0.13851(13) 0.0510(6) Uani 1 1 d . . . . .
H39 H -0.3504 0.3944 0.1725 0.061 Uiso 1 1 calc R U . . .
C40 C -0.3532(3) 0.3635(2) 0.07341(13) 0.0536(6) Uani 1 1 d . . . . .
H40 H -0.4513 0.3602 0.0634 0.064 Uiso 1 1 calc R U . . .
C41 C -0.2674(3) 0.34844(19) 0.02353(12) 0.0516(6) Uani 1 1 d . . . . .
H41 H -0.3078 0.3347 -0.0204 0.062 Uiso 1 1 calc R U . . .
C42 C -0.1206(2) 0.35360(17) 0.03817(11) 0.0447(5) Uani 1 1 d . . . . .
H42 H -0.0635 0.3441 0.0039 0.054 Uiso 1 1 calc R U . . .
C43 C 0.2042(2) 0.33021(16) 0.05101(10) 0.0383(4) Uani 1 1 d . . . . .
C44 C 0.2355(3) 0.22882(18) 0.03629(12) 0.0484(5) Uani 1 1 d . . . . .
H44 H 0.2210 0.1846 0.0663 0.058 Uiso 1 1 calc R U . . .
C45 C 0.2879(3) 0.1923(2) -0.02239(13) 0.0598(7) Uani 1 1 d . . . . .
H45 H 0.3075 0.1238 -0.0316 0.072 Uiso 1 1 calc R U . . .
C46 C 0.3110(3) 0.2557(2) -0.06683(13) 0.0605(7) Uani 1 1 d . . . . .
H46 H 0.3467 0.2308 -0.1062 0.073 Uiso 1 1 calc R U . . .
C47 C 0.2812(4) 0.3571(2) -0.05311(14) 0.0696(8) Uani 1 1 d . . . . .
H47 H 0.2967 0.4009 -0.0833 0.084 Uiso 1 1 calc R U . . .
C48 C 0.2284(3) 0.3938(2) 0.00537(13) 0.0598(7) Uani 1 1 d . . . . .
H48 H 0.2088 0.4624 0.0142 0.072 Uiso 1 1 calc R U . . .
C49 C 0.2031(2) 0.51344(16) 0.14484(10) 0.0390(5) Uani 1 1 d . . . . .
C50 C 0.1224(3) 0.59249(17) 0.13522(11) 0.0436(5) Uani 1 1 d . . . . .
H50 H 0.0250 0.5766 0.1216 0.052 Uiso 1 1 calc R U . . .
C51 C 0.1871(3) 0.69544(18) 0.14596(12) 0.0536(6) Uani 1 1 d . . . . .
H51 H 0.1327 0.7482 0.1394 0.064 Uiso 1 1 calc R U . . .
C52 C 0.3309(3) 0.71995(19) 0.16619(12) 0.0549(6) Uani 1 1 d . . . . .
H52 H 0.3734 0.7890 0.1731 0.066 Uiso 1 1 calc R U . . .
C53 C 0.4122(3) 0.6425(2) 0.17624(12) 0.0542(6) Uani 1 1 d . . . . .
H53 H 0.5094 0.6590 0.1901 0.065 Uiso 1 1 calc R U . . .
C54 C 0.3482(3) 0.53950(18) 0.16560(12) 0.0475(5) Uani 1 1 d . . . . .
H54 H 0.4032 0.4872 0.1725 0.057 Uiso 1 1 calc R U . . .
C55 C 0.6771(5) 0.1733(4) 0.4314(2) 0.1058(9) Uani 1 1 d . . . . .
C56 C 0.6732(5) 0.1831(3) 0.36331(19) 0.1058(9) Uani 1 1 d . . . . .
H56A H 0.6244 0.1199 0.3358 0.159 Uiso 1 1 calc R U . . .
H56B H 0.7688 0.1951 0.3523 0.159 Uiso 1 1 calc R U . . .
H56C H 0.6236 0.2407 0.3563 0.159 Uiso 1 1 calc R U . . .
Br1 Br 0.44090(2) 0.31170(2) 0.24729(2) 0.04617(8) Uani 1 1 d . . . . .
Cl1 Cl -0.37714(7) 0.62108(6) 0.53676(3) 0.06202(17) Uani 1 1 d . . . . .
Cu1 Cu 0.17569(3) 0.28900(2) 0.21441(2) 0.03601(8) Uani 1 1 d . . . . .
N1 N 0.1200(2) 0.55375(15) 0.39043(9) 0.0437(4) Uani 1 1 d . . . . .
N2 N 0.2885(2) 0.50545(15) 0.32510(9) 0.0436(4) Uani 1 1 d . . . . .
N3 N 0.3713(2) 0.59831(15) 0.35267(9) 0.0436(4) Uani 1 1 d . . . . .
N4 N 0.6792(4) 0.1633(3) 0.48122(17) 0.0995(10) Uani 1 1 d . . . . .
P1 P 0.12278(5) 0.11356(4) 0.20775(3) 0.03391(12) Uani 1 1 d . . . . .
P2 P 0.13198(6) 0.37438(4) 0.12852(3) 0.03541(12) Uani 1 1 d . . . . .
S1 S 0.06243(6) 0.36515(4) 0.30699(3) 0.03968(12) Uani 1 1 d . . . . .
H1 H 0.184(3) 0.606(2) 0.4014(12) 0.048 Uiso 1 1 d . U . . .
H2A H 0.323(3) 0.456(2) 0.3031(12) 0.048 Uiso 1 1 d . U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.384(3) . ?
C1 C6 1.388(3) . ?
C1 N1 1.409(3) . ?
C2 C3 1.381(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.374(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.372(4) . ?
C4 Cl1 1.735(2) . ?
C5 C6 1.381(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 N1 1.341(3) . ?
C7 N2 1.345(3) . ?
C7 S1 1.696(2) . ?
C8 N3 1.283(3) . ?
C8 C9 1.456(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.377(3) . ?
C9 C18 1.432(3) . ?
C10 C11 1.402(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.359(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.404(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.413(3) . ?
C13 C18 1.431(3) . ?
C14 C15 1.356(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.400(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.363(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.413(3) . ?
C17 H17 0.9300 . ?
C19 C20 1.379(3) . ?
C19 C24 1.390(3) . ?
C19 P1 1.827(2) . ?
C20 C21 1.384(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.380(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.377(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.378(3) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 C30 1.384(3) . ?
C25 C26 1.388(3) . ?
C25 P1 1.821(2) . ?
C26 C27 1.380(3) . ?
C26 H26 0.9300 . ?
C27 C28 1.370(4) . ?
C27 H27 0.9300 . ?
C28 C29 1.378(4) . ?
C28 H28 0.9300 . ?
C29 C30 1.383(3) . ?
C29 H29 0.9300 . ?
C30 H30 0.9300 . ?
C31 C32 1.390(3) . ?
C31 C36 1.392(3) . ?
C31 P1 1.823(2) . ?
C32 C33 1.383(3) . ?
C32 H32 0.9300 . ?
C33 C34 1.380(4) . ?
C33 H33 0.9300 . ?
C34 C35 1.371(4) . ?
C34 H34 0.9300 . ?
C35 C36 1.394(3) . ?
C35 H35 0.9300 . ?
C36 H36 0.9300 . ?
C37 C42 1.388(3) . ?
C37 C38 1.395(3) . ?
C37 P2 1.831(2) . ?
C38 C39 1.382(3) . ?
C38 H38 0.9300 . ?
C39 C40 1.380(4) . ?
C39 H39 0.9300 . ?
C40 C41 1.373(4) . ?
C40 H40 0.9300 . ?
C41 C42 1.390(3) . ?
C41 H41 0.9300 . ?
C42 H42 0.9300 . ?
C43 C48 1.383(3) . ?
C43 C44 1.383(3) . ?
C43 P2 1.827(2) . ?
C44 C45 1.381(3) . ?
C44 H44 0.9300 . ?
C45 C46 1.360(4) . ?
C45 H45 0.9300 . ?
C46 C47 1.377(4) . ?
C46 H46 0.9300 . ?
C47 C48 1.380(4) . ?
C47 H47 0.9300 . ?
C48 H48 0.9300 . ?
C49 C50 1.389(3) . ?
C49 C54 1.390(3) . ?
C49 P2 1.833(2) . ?
C50 C51 1.390(3) . ?
C50 H50 0.9300 . ?
C51 C52 1.375(4) . ?
C51 H51 0.9300 . ?
C52 C53 1.377(4) . ?
C52 H52 0.9300 . ?
C53 C54 1.389(3) . ?
C53 H53 0.9300 . ?
C54 H54 0.9300 . ?
C55 N4 1.060(5) . ?
C55 C56 1.432(6) . ?
C56 H56A 0.9600 . ?
C56 H56B 0.9600 . ?
C56 H56C 0.9600 . ?
Br1 Cu1 2.5169(3) . ?
Cu1 P1 2.2769(6) . ?
Cu1 P2 2.2904(6) . ?
Cu1 S1 2.4011(6) . ?
N1 H1 0.85(3) . ?
N2 N3 1.372(3) . ?
N2 H2A 0.84(3) . ?

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
C2 C1 C6 118.9(2) . . ?
C2 C1 N1 126.1(2) . . ?
C6 C1 N1 114.9(2) . . ?
C3 C2 C1 119.9(2) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C4 C3 C2 120.5(2) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C5 C4 C3 120.3(2) . . ?
C5 C4 Cl1 119.07(18) . . ?
C3 C4 Cl1 120.63(19) . . ?
C4 C5 C6 119.4(2) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C5 C6 C1 120.9(2) . . ?
C5 C6 H6 119.5 . . ?
C1 C6 H6 119.5 . . ?
N1 C7 N2 114.73(19) . . ?
N1 C7 S1 126.94(17) . . ?
N2 C7 S1 118.33(16) . . ?
N3 C8 C9 122.0(2) . . ?
N3 C8 H8 119.0 . . ?
C9 C8 H8 119.0 . . ?
C10 C9 C18 119.8(2) . . ?
C10 C9 C8 120.1(2) . . ?
C18 C9 C8 120.1(2) . . ?
C9 C10 C11 120.9(2) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
C12 C11 C10 120.4(2) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C13 121.3(2) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 H12 119.3 . . ?
C12 C13 C14 121.6(2) . . ?
C12 C13 C18 119.1(2) . . ?
C14 C13 C18 119.3(2) . . ?
C15 C14 C13 121.4(2) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C14 C15 C16 119.7(2) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C17 C16 C15 120.7(2) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C16 C17 C18 121.7(2) . . ?
C16 C17 H17 119.2 . . ?
C18 C17 H17 119.2 . . ?
C17 C18 C13 117.2(2) . . ?
C17 C18 C9 124.4(2) . . ?
C13 C18 C9 118.4(2) . . ?
C20 C19 C24 118.53(19) . . ?
C20 C19 P1 118.27(16) . . ?
C24 C19 P1 123.19(16) . . ?
C19 C20 C21 120.6(2) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 H20 119.7 . . ?
C22 C21 C20 120.4(2) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C23 C22 C21 119.4(2) . . ?
C23 C22 H22 120.3 . . ?
C21 C22 H22 120.3 . . ?
C22 C23 C24 120.2(2) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 H23 119.9 . . ?
C23 C24 C19 120.9(2) . . ?
C23 C24 H24 119.6 . . ?
C19 C24 H24 119.6 . . ?
C30 C25 C26 118.6(2) . . ?
C30 C25 P1 117.99(16) . . ?
C26 C25 P1 123.42(17) . . ?
C27 C26 C25 120.6(2) . . ?
C27 C26 H26 119.7 . . ?
C25 C26 H26 119.7 . . ?
C28 C27 C26 120.2(2) . . ?
C28 C27 H27 119.9 . . ?
C26 C27 H27 119.9 . . ?
C27 C28 C29 119.9(2) . . ?
C27 C28 H28 120.0 . . ?
C29 C28 H28 120.0 . . ?
C28 C29 C30 120.0(2) . . ?
C28 C29 H29 120.0 . . ?
C30 C29 H29 120.0 . . ?
C29 C30 C25 120.6(2) . . ?
C29 C30 H30 119.7 . . ?
C25 C30 H30 119.7 . . ?
C32 C31 C36 118.8(2) . . ?
C32 C31 P1 117.47(16) . . ?
C36 C31 P1 123.58(18) . . ?
C33 C32 C31 121.0(2) . . ?
C33 C32 H32 119.5 . . ?
C31 C32 H32 119.5 . . ?
C34 C33 C32 119.9(2) . . ?
C34 C33 H33 120.1 . . ?
C32 C33 H33 120.1 . . ?
C35 C34 C33 119.8(2) . . ?
C35 C34 H34 120.1 . . ?
C33 C34 H34 120.1 . . ?
C34 C35 C36 121.0(2) . . ?
C34 C35 H35 119.5 . . ?
C36 C35 H35 119.5 . . ?
C31 C36 C35 119.5(2) . . ?
C31 C36 H36 120.2 . . ?
C35 C36 H36 120.2 . . ?
C42 C37 C38 118.1(2) . . ?
C42 C37 P2 124.38(17) . . ?
C38 C37 P2 117.45(16) . . ?
C39 C38 C37 121.0(2) . . ?
C39 C38 H38 119.5 . . ?
C37 C38 H38 119.5 . . ?
C40 C39 C38 120.2(2) . . ?
C40 C39 H39 119.9 . . ?
C38 C39 H39 119.9 . . ?
C41 C40 C39 119.5(2) . . ?
C41 C40 H40 120.2 . . ?
C39 C40 H40 120.2 . . ?
C40 C41 C42 120.5(2) . . ?
C40 C41 H41 119.7 . . ?
C42 C41 H41 119.7 . . ?
C37 C42 C41 120.6(2) . . ?
C37 C42 H42 119.7 . . ?
C41 C42 H42 119.7 . . ?
C48 C43 C44 117.8(2) . . ?
C48 C43 P2 122.81(17) . . ?
C44 C43 P2 119.39(16) . . ?
C45 C44 C43 120.9(2) . . ?
C45 C44 H44 119.6 . . ?
C43 C44 H44 119.6 . . ?
C46 C45 C44 120.6(2) . . ?
C46 C45 H45 119.7 . . ?
C44 C45 H45 119.7 . . ?
C45 C46 C47 119.5(2) . . ?
C45 C46 H46 120.3 . . ?
C47 C46 H46 120.3 . . ?
C46 C47 C48 120.0(2) . . ?
C46 C47 H47 120.0 . . ?
C48 C47 H47 120.0 . . ?
C47 C48 C43 121.1(2) . . ?
C47 C48 H48 119.4 . . ?
C43 C48 H48 119.4 . . ?
C50 C49 C54 118.8(2) . . ?
C50 C49 P2 124.04(17) . . ?
C54 C49 P2 117.09(17) . . ?
C49 C50 C51 120.0(2) . . ?
C49 C50 H50 120.0 . . ?
C51 C50 H50 120.0 . . ?
C52 C51 C50 120.5(2) . . ?
C52 C51 H51 119.7 . . ?
C50 C51 H51 119.7 . . ?
C51 C52 C53 120.1(2) . . ?
C51 C52 H52 119.9 . . ?
C53 C52 H52 119.9 . . ?
C52 C53 C54 119.6(2) . . ?
C52 C53 H53 120.2 . . ?
C54 C53 H53 120.2 . . ?
C53 C54 C49 120.9(2) . . ?
C53 C54 H54 119.5 . . ?
C49 C54 H54 119.5 . . ?
N4 C55 C56 178.0(5) . . ?
C55 C56 H56A 109.5 . . ?
C55 C56 H56B 109.5 . . ?
H56A C56 H56B 109.5 . . ?
C55 C56 H56C 109.5 . . ?
H56A C56 H56C 109.5 . . ?
H56B C56 H56C 109.5 . . ?
P1 Cu1 P2 124.51(2) . . ?
P1 Cu1 S1 104.49(2) . . ?
P2 Cu1 S1 109.25(2) . . ?
P1 Cu1 Br1 100.286(17) . . ?
P2 Cu1 Br1 108.407(17) . . ?
S1 Cu1 Br1 108.968(17) . . ?
C7 N1 C1 133.8(2) . . ?
C7 N1 H1 111.2(17) . . ?
C1 N1 H1 114.9(17) . . ?
C7 N2 N3 121.13(18) . . ?
C7 N2 H2A 116.2(18) . . ?
N3 N2 H2A 121.3(18) . . ?
C8 N3 N2 114.85(18) . . ?
C25 P1 C31 103.96(10) . . ?
C25 P1 C19 103.31(9) . . ?
C31 P1 C19 102.47(9) . . ?
C25 P1 Cu1 116.01(7) . . ?
C31 P1 Cu1 115.69(7) . . ?
C19 P1 Cu1 113.70(7) . . ?
C43 P2 C37 104.04(10) . . ?
C43 P2 C49 100.32(9) . . ?
C37 P2 C49 103.80(10) . . ?
C43 P2 Cu1 118.23(7) . . ?
C37 P2 Cu1 113.22(7) . . ?
C49 P2 Cu1 115.33(7) . . ?
C7 S1 Cu1 109.09(7) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.6(4) . . . . ?
N1 C1 C2 C3 179.6(2) . . . . ?
C1 C2 C3 C4 0.0(4) . . . . ?
C2 C3 C4 C5 0.4(4) . . . . ?
C2 C3 C4 Cl1 -179.4(2) . . . . ?
C3 C4 C5 C6 -0.2(4) . . . . ?
Cl1 C4 C5 C6 179.64(19) . . . . ?
C4 C5 C6 C1 -0.5(4) . . . . ?
C2 C1 C6 C5 0.9(4) . . . . ?
N1 C1 C6 C5 -179.3(2) . . . . ?
N3 C8 C9 C10 4.3(3) . . . . ?
N3 C8 C9 C18 -176.1(2) . . . . ?
C18 C9 C10 C11 -0.7(3) . . . . ?
C8 C9 C10 C11 178.9(2) . . . . ?
C9 C10 C11 C12 -0.9(4) . . . . ?
C10 C11 C12 C13 0.8(4) . . . . ?
C11 C12 C13 C14 -179.6(2) . . . . ?
C11 C12 C13 C18 0.8(4) . . . . ?
C12 C13 C14 C15 -178.5(2) . . . . ?
C18 C13 C14 C15 1.1(4) . . . . ?
C13 C14 C15 C16 0.6(4) . . . . ?
C14 C15 C16 C17 -1.7(4) . . . . ?
C15 C16 C17 C18 1.0(4) . . . . ?
C16 C17 C18 C13 0.7(4) . . . . ?
C16 C17 C18 C9 -179.1(2) . . . . ?
C12 C13 C18 C17 177.9(2) . . . . ?
C14 C13 C18 C17 -1.8(3) . . . . ?
C12 C13 C18 C9 -2.3(3) . . . . ?
C14 C13 C18 C9 178.1(2) . . . . ?
C10 C9 C18 C17 -178.0(2) . . . . ?
C8 C9 C18 C17 2.5(3) . . . . ?
C10 C9 C18 C13 2.2(3) . . . . ?
C8 C9 C18 C13 -177.4(2) . . . . ?
C24 C19 C20 C21 -1.3(4) . . . . ?
P1 C19 C20 C21 177.5(2) . . . . ?
C19 C20 C21 C22 0.7(5) . . . . ?
C20 C21 C22 C23 1.0(5) . . . . ?
C21 C22 C23 C24 -2.2(4) . . . . ?
C22 C23 C24 C19 1.6(4) . . . . ?
C20 C19 C24 C23 0.1(3) . . . . ?
P1 C19 C24 C23 -178.60(18) . . . . ?
C30 C25 C26 C27 -0.6(4) . . . . ?
P1 C25 C26 C27 178.5(2) . . . . ?
C25 C26 C27 C28 0.6(4) . . . . ?
C26 C27 C28 C29 0.1(4) . . . . ?
C27 C28 C29 C30 -0.7(4) . . . . ?
C28 C29 C30 C25 0.6(4) . . . . ?
C26 C25 C30 C29 0.1(4) . . . . ?
P1 C25 C30 C29 -179.1(2) . . . . ?
C36 C31 C32 C33 -1.1(3) . . . . ?
P1 C31 C32 C33 -177.22(19) . . . . ?
C31 C32 C33 C34 1.6(4) . . . . ?
C32 C33 C34 C35 -0.5(4) . . . . ?
C33 C34 C35 C36 -1.1(4) . . . . ?
C32 C31 C36 C35 -0.4(3) . . . . ?
P1 C31 C36 C35 175.42(18) . . . . ?
C34 C35 C36 C31 1.5(4) . . . . ?
C42 C37 C38 C39 -0.3(3) . . . . ?
P2 C37 C38 C39 -177.57(18) . . . . ?
C37 C38 C39 C40 0.8(4) . . . . ?
C38 C39 C40 C41 -0.6(4) . . . . ?
C39 C40 C41 C42 -0.2(4) . . . . ?
C38 C37 C42 C41 -0.5(3) . . . . ?
P2 C37 C42 C41 176.58(18) . . . . ?
C40 C41 C42 C37 0.8(4) . . . . ?
C48 C43 C44 C45 -0.6(4) . . . . ?
P2 C43 C44 C45 178.9(2) . . . . ?
C43 C44 C45 C46 0.5(4) . . . . ?
C44 C45 C46 C47 -0.3(5) . . . . ?
C45 C46 C47 C48 0.1(5) . . . . ?
C46 C47 C48 C43 -0.1(5) . . . . ?
C44 C43 C48 C47 0.4(4) . . . . ?
P2 C43 C48 C47 -179.0(2) . . . . ?
C54 C49 C50 C51 0.4(3) . . . . ?
P2 C49 C50 C51 -176.93(17) . . . . ?
C49 C50 C51 C52 -0.1(3) . . . . ?
C50 C51 C52 C53 -0.2(4) . . . . ?
C51 C52 C53 C54 0.2(4) . . . . ?
C52 C53 C54 C49 0.1(4) . . . . ?
C50 C49 C54 C53 -0.4(3) . . . . ?
P2 C49 C54 C53 177.12(18) . . . . ?
N2 C7 N1 C1 177.7(2) . . . . ?
S1 C7 N1 C1 -2.7(4) . . . . ?
C2 C1 N1 C7 0.3(4) . . . . ?
C6 C1 N1 C7 -179.5(2) . . . . ?
N1 C7 N2 N3 -0.6(3) . . . . ?
S1 C7 N2 N3 179.73(16) . . . . ?
C9 C8 N3 N2 178.50(19) . . . . ?
C7 N2 N3 C8 172.2(2) . . . . ?
C30 C25 P1 C31 -104.63(19) . . . . ?
C26 C25 P1 C31 76.2(2) . . . . ?
C30 C25 P1 C19 148.67(18) . . . . ?
C26 C25 P1 C19 -30.5(2) . . . . ?
C30 C25 P1 Cu1 23.6(2) . . . . ?
C26 C25 P1 Cu1 -155.58(18) . . . . ?
C32 C31 P1 C25 -171.76(17) . . . . ?
C36 C31 P1 C25 12.3(2) . . . . ?
C32 C31 P1 C19 -64.42(19) . . . . ?
C36 C31 P1 C19 119.66(19) . . . . ?
C32 C31 P1 Cu1 59.85(18) . . . . ?
C36 C31 P1 Cu1 -116.06(18) . . . . ?
C20 C19 P1 C25 -90.4(2) . . . . ?
C24 C19 P1 C25 88.4(2) . . . . ?
C20 C19 P1 C31 161.80(19) . . . . ?
C24 C19 P1 C31 -19.5(2) . . . . ?
C20 C19 P1 Cu1 36.2(2) . . . . ?
C24 C19 P1 Cu1 -145.06(17) . . . . ?
C48 C43 P2 C37 76.4(2) . . . . ?
C44 C43 P2 C37 -103.00(19) . . . . ?
C48 C43 P2 C49 -30.8(2) . . . . ?
C44 C43 P2 C49 149.81(19) . . . . ?
C48 C43 P2 Cu1 -157.05(19) . . . . ?
C44 C43 P2 Cu1 23.6(2) . . . . ?
C42 C37 P2 C43 -6.8(2) . . . . ?
C38 C37 P2 C43 170.31(17) . . . . ?
C42 C37 P2 C49 97.79(19) . . . . ?
C38 C37 P2 C49 -85.11(18) . . . . ?
C42 C37 P2 Cu1 -136.43(17) . . . . ?
C38 C37 P2 Cu1 40.67(18) . . . . ?
C50 C49 P2 C43 104.41(19) . . . . ?
C54 C49 P2 C43 -72.97(18) . . . . ?
C50 C49 P2 C37 -3.0(2) . . . . ?
C54 C49 P2 C37 179.65(17) . . . . ?
C50 C49 P2 Cu1 -127.41(17) . . . . ?
C54 C49 P2 Cu1 55.21(18) . . . . ?
N1 C7 S1 Cu1 169.65(18) . . . . ?
N2 C7 S1 Cu1 -10.69(19) . . . . ?

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
N2 H2A Br1 0.84(3) 2.48(3) 3.312(2) 175(2) .
N1 H1 N3 0.85(3) 2.13(3) 2.616(3) 116(2) .

_refine_diff_density_max         0.789
_refine_diff_density_min         -0.755
_refine_diff_density_rms         0.047

####################################################################### 
# 
# 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_sb9_0m
_database_code_depnum_ccdc_archive 'CCDC 1002350'
_audit_update_record             
;
2014-05-12 deposited with the CCDC.
2015-02-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H15 Cu F N4 O S'
_chemical_formula_sum            'C19 H15 Cu F N4 O S'
_chemical_formula_weight         429.95

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'
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'
F F 0.0171 0.0103 '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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_Int_Tables_number      14

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                   13.3041(5)
_cell_length_b                   5.8394(2)
_cell_length_c                   23.1869(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.115(2)
_cell_angle_gamma                90.00
_cell_volume                     1761.22(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6898
_cell_measurement_theta_min      2.62
_cell_measurement_theta_max      28.23

_exptl_crystal_description       rectangular
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.621
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             876
_exptl_absorpt_coefficient_mu    1.386
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.7787
_exptl_absorpt_correction_T_max  0.9728
_exptl_absorpt_process_details   sadabs

_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 0.3
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            33365
_diffrn_reflns_av_R_equivalents  0.0410
_diffrn_reflns_av_sigmaI/netI    0.0312
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         1.80
_diffrn_reflns_theta_max         30.5
_reflns_number_total             5407
_reflns_number_gt                3927
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Bruker Kappa Apex CCD'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    SHELXS-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ORTEP-III
_computing_publication_material  WinGXv1.80.05

_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 > 2σ(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)+(0.0386P)²+0.5828P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5407
_refine_ls_number_parameters     304
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0581
_refine_ls_R_factor_gt           0.0345
_refine_ls_wR_factor_ref         0.0885
_refine_ls_wR_factor_gt          0.0796
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_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
Cu1 Cu 0.183488(16) 0.54032(4) 0.445702(10) 0.03707(8) Uani 1 1 d . . .
S1 S 0.09241(4) 0.25069(10) 0.47291(2) 0.04538(14) Uani 1 1 d . . .
F1 F -0.45315(10) 0.0075(2) 0.24739(7) 0.0649(4) Uani 1 1 d . . .
O1 O 0.26273(10) 0.7769(3) 0.42016(7) 0.0475(4) Uani 1 1 d . . .
N1 N -0.09238(13) 0.1416(3) 0.41190(8) 0.0428(4) Uani 1 1 d . . .
N2 N -0.02582(11) 0.4701(3) 0.37997(7) 0.0384(4) Uani 1 1 d . . .
N3 N 0.06127(11) 0.6079(3) 0.38677(7) 0.0346(3) Uani 1 1 d . . .
N4 N 0.30867(12) 0.4751(3) 0.50910(7) 0.0365(3) Uani 1 1 d . . .
C1 C -0.18231(13) 0.1165(3) 0.36799(8) 0.0350(4) Uani 1 1 d . . .
C2 C -0.23686(16) -0.0865(4) 0.36829(10) 0.0427(5) Uani 1 1 d . . .
C3 C -0.32825(17) -0.1234(4) 0.32808(10) 0.0466(5) Uani 1 1 d . . .
C4 C -0.36354(15) 0.0430(4) 0.28748(10) 0.0439(5) Uani 1 1 d . . .
C5 C -0.31124(16) 0.2415(4) 0.28482(10) 0.0471(5) Uani 1 1 d . . .
C6 C -0.21978(15) 0.2799(4) 0.32549(10) 0.0446(5) Uani 1 1 d . . .
C7 C -0.01537(13) 0.3002(3) 0.41666(8) 0.0354(4) Uani 1 1 d . . .
C8 C 0.05156(14) 0.7769(3) 0.34986(8) 0.0368(4) Uani 1 1 d . . .
C9 C 0.13016(14) 0.9348(3) 0.34348(8) 0.0357(4) Uani 1 1 d . . .
C10 C 0.10414(17) 1.1082(4) 0.30048(10) 0.0474(5) Uani 1 1 d . . .
C11 C 0.17393(19) 1.2650(4) 0.29017(10) 0.0545(6) Uani 1 1 d . . .
C12 C 0.27449(18) 1.2511(4) 0.32233(10) 0.0539(6) Uani 1 1 d . . .
C13 C 0.30243(16) 1.0844(4) 0.36428(10) 0.0495(6) Uani 1 1 d . . .
C14 C 0.23188(14) 0.9243(3) 0.37735(8) 0.0381(4) Uani 1 1 d . . .
C15 C 0.34760(16) 0.6366(4) 0.54842(10) 0.0439(5) Uani 1 1 d . . .
C16 C 0.43935(17) 0.6092(4) 0.58824(10) 0.0504(5) Uani 1 1 d . . .
C17 C 0.49499(16) 0.4150(5) 0.58664(10) 0.0520(6) Uani 1 1 d . . .
C18 C 0.45499(18) 0.2466(5) 0.54722(10) 0.0541(6) Uani 1 1 d . . .
C19 C 0.36097(16) 0.2798(4) 0.51007(9) 0.0447(5) Uani 1 1 d . . .
H1 H -0.0814(17) 0.033(4) 0.4356(10) 0.045(6) Uiso 1 1 d . . .
H2 H -0.2124(17) -0.196(4) 0.3950(10) 0.049(6) Uiso 1 1 d . . .
H3 H -0.3637(18) -0.246(4) 0.3278(10) 0.056(7) Uiso 1 1 d . . .
H5 H -0.3348(16) 0.351(4) 0.2574(10) 0.050(6) Uiso 1 1 d . . .
H6 H -0.1849(17) 0.411(4) 0.3254(10) 0.047(6) Uiso 1 1 d . . .
H8 H -0.0132(14) 0.792(3) 0.3245(8) 0.032(5) Uiso 1 1 d . . .
H10 H 0.0372(17) 1.118(4) 0.2807(10) 0.051(6) Uiso 1 1 d . . .
H11 H 0.1579(18) 1.384(4) 0.2620(11) 0.064(7) Uiso 1 1 d . . .
H12 H 0.3252(17) 1.344(4) 0.3152(10) 0.054(6) Uiso 1 1 d . . .
H13 H 0.365(2) 1.070(4) 0.3838(12) 0.063(8) Uiso 1 1 d . . .
H15 H 0.3100(15) 0.771(4) 0.5460(9) 0.040(6) Uiso 1 1 d . . .
H16 H 0.458(2) 0.728(5) 0.6127(12) 0.070(8) Uiso 1 1 d . . .
H17 H 0.5525(19) 0.383(4) 0.6114(11) 0.060(7) Uiso 1 1 d . . .
H18 H 0.486(2) 0.108(5) 0.5437(12) 0.073(8) Uiso 1 1 d . . .
H19 H 0.3269(18) 0.166(4) 0.4824(11) 0.060(7) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.9061(14) . ?
Cu1 N3 1.9323(15) . ?
Cu1 N4 2.0130(15) . ?
Cu1 S1 2.2467(6) . ?
S1 C7 1.7481(18) . ?
F1 C4 1.365(2) . ?
O1 C14 1.313(2) . ?
N1 C7 1.368(2) . ?
N1 C1 1.407(2) . ?
N2 C7 1.295(2) . ?
N2 N3 1.392(2) . ?
N3 C8 1.295(2) . ?
N4 C19 1.334(3) . ?
N4 C15 1.338(3) . ?
C1 C6 1.387(3) . ?
C1 C2 1.391(3) . ?
C2 C3 1.385(3) . ?
C3 C4 1.366(3) . ?
C4 C5 1.360(3) . ?
C5 C6 1.392(3) . ?
C8 C9 1.425(3) . ?
C9 C10 1.412(3) . ?
C9 C14 1.416(3) . ?
C10 C11 1.361(3) . ?
C11 C12 1.391(3) . ?
C12 C13 1.371(3) . ?
C13 C14 1.402(3) . ?
C15 C16 1.377(3) . ?
C16 C17 1.359(4) . ?
C17 C18 1.372(3) . ?
C18 C19 1.375(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 N3 94.04(6) . . ?
O1 Cu1 N4 86.40(6) . . ?
N3 Cu1 N4 178.10(7) . . ?
O1 Cu1 S1 177.42(5) . . ?
N3 Cu1 S1 85.93(5) . . ?
N4 Cu1 S1 93.71(5) . . ?
C7 S1 Cu1 94.14(7) . . ?
C14 O1 Cu1 127.19(12) . . ?
C7 N1 C1 129.63(17) . . ?
C7 N2 N3 113.34(15) . . ?
C8 N3 N2 113.60(15) . . ?
C8 N3 Cu1 125.13(13) . . ?
N2 N3 Cu1 121.26(12) . . ?
C19 N4 C15 117.73(17) . . ?
C19 N4 Cu1 121.53(13) . . ?
C15 N4 Cu1 120.44(14) . . ?
C6 C1 C2 118.67(18) . . ?
C6 C1 N1 124.53(18) . . ?
C2 C1 N1 116.80(18) . . ?
C3 C2 C1 121.0(2) . . ?
C4 C3 C2 118.7(2) . . ?
C5 C4 F1 118.7(2) . . ?
C5 C4 C3 122.17(19) . . ?
F1 C4 C3 119.10(19) . . ?
C4 C5 C6 119.3(2) . . ?
C1 C6 C5 120.21(19) . . ?
N2 C7 N1 119.35(17) . . ?
N2 C7 S1 125.09(14) . . ?
N1 C7 S1 115.55(14) . . ?
N3 C8 C9 126.02(17) . . ?
C10 C9 C14 119.12(18) . . ?
C10 C9 C8 117.43(17) . . ?
C14 C9 C8 123.44(17) . . ?
C11 C10 C9 122.10(19) . . ?
C10 C11 C12 118.8(2) . . ?
C13 C12 C11 120.6(2) . . ?
C12 C13 C14 122.18(19) . . ?
O1 C14 C13 118.90(17) . . ?
O1 C14 C9 123.95(17) . . ?
C13 C14 C9 117.15(18) . . ?
N4 C15 C16 122.5(2) . . ?
C17 C16 C15 119.4(2) . . ?
C16 C17 C18 118.6(2) . . ?
C17 C18 C19 119.4(2) . . ?
N4 C19 C18 122.3(2) . . ?

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
N3 Cu1 S1 C7 3.56(8) . . . . ?
N4 Cu1 S1 C7 -178.31(8) . . . . ?
N3 Cu1 O1 C14 1.50(18) . . . . ?
N4 Cu1 O1 C14 -176.65(18) . . . . ?
C7 N2 N3 C8 179.44(17) . . . . ?
C7 N2 N3 Cu1 0.5(2) . . . . ?
O1 Cu1 N3 C8 -4.43(17) . . . . ?
S1 Cu1 N3 C8 178.16(17) . . . . ?
O1 Cu1 N3 N2 174.39(14) . . . . ?
S1 Cu1 N3 N2 -3.02(13) . . . . ?
O1 Cu1 N4 C19 -113.35(17) . . . . ?
S1 Cu1 N4 C19 64.06(16) . . . . ?
O1 Cu1 N4 C15 60.19(16) . . . . ?
S1 Cu1 N4 C15 -122.40(15) . . . . ?
C7 N1 C1 C6 -12.9(3) . . . . ?
C7 N1 C1 C2 167.7(2) . . . . ?
C6 C1 C2 C3 -1.7(3) . . . . ?
N1 C1 C2 C3 177.7(2) . . . . ?
C1 C2 C3 C4 0.7(3) . . . . ?
C2 C3 C4 C5 0.9(3) . . . . ?
C2 C3 C4 F1 179.53(19) . . . . ?
F1 C4 C5 C6 179.9(2) . . . . ?
C3 C4 C5 C6 -1.4(4) . . . . ?
C2 C1 C6 C5 1.2(3) . . . . ?
N1 C1 C6 C5 -178.2(2) . . . . ?
C4 C5 C6 C1 0.4(3) . . . . ?
N3 N2 C7 N1 -175.18(17) . . . . ?
N3 N2 C7 S1 3.8(3) . . . . ?
C1 N1 C7 N2 7.3(3) . . . . ?
C1 N1 C7 S1 -171.75(17) . . . . ?
Cu1 S1 C7 N2 -5.22(18) . . . . ?
Cu1 S1 C7 N1 173.81(15) . . . . ?
N2 N3 C8 C9 -174.92(18) . . . . ?
Cu1 N3 C8 C9 4.0(3) . . . . ?
N3 C8 C9 C10 -180.0(2) . . . . ?
N3 C8 C9 C14 0.7(3) . . . . ?
C14 C9 C10 C11 0.5(4) . . . . ?
C8 C9 C10 C11 -178.8(2) . . . . ?
C9 C10 C11 C12 1.2(4) . . . . ?
C10 C11 C12 C13 -1.0(4) . . . . ?
C11 C12 C13 C14 -1.0(4) . . . . ?
Cu1 O1 C14 C13 -178.86(16) . . . . ?
Cu1 O1 C14 C9 2.1(3) . . . . ?
C12 C13 C14 O1 -176.5(2) . . . . ?
C12 C13 C14 C9 2.6(3) . . . . ?
C10 C9 C14 O1 176.7(2) . . . . ?
C8 C9 C14 O1 -4.0(3) . . . . ?
C10 C9 C14 C13 -2.3(3) . . . . ?
C8 C9 C14 C13 177.0(2) . . . . ?
C19 N4 C15 C16 1.3(3) . . . . ?
Cu1 N4 C15 C16 -172.46(17) . . . . ?
N4 C15 C16 C17 2.4(3) . . . . ?
C15 C16 C17 C18 -3.4(4) . . . . ?
C16 C17 C18 C19 0.9(4) . . . . ?
C15 N4 C19 C18 -4.0(3) . . . . ?
Cu1 N4 C19 C18 169.68(18) . . . . ?
C17 C18 C19 N4 3.0(4) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        30.5
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.315
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.053
####################################################################### 
# 
# 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_sb4_m
_database_code_depnum_ccdc_archive 'CCDC 1002351'
_audit_update_record             
;
2015-01-30 deposited with the CCDC.
2015-02-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C44 H36 Cl4 Cu4 N16 S4, 2(H2 O)'
_chemical_formula_sum            'C44 H40 Cl4 Cu4 N16 O2 S4'
_chemical_melting_point          ?

_exptl_crystal_description       'rectangular plate like'
_exptl_crystal_colour            'dark blue'
_diffrn_ambient_temperature      273(2)
_chemical_formula_weight         1349.12

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 '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'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   8.9472(15)
_cell_length_b                   9.8129(16)
_cell_length_c                   14.928(2)
_cell_angle_alpha                85.086(3)
_cell_angle_beta                 72.973(3)
_cell_angle_gamma                80.782(3)
_cell_volume                     1236.0(4)
_cell_formula_units_Z            1
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    1162
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      21.99


_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.813
_exptl_crystal_F_000             680
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.090
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    2.142
_shelx_estimated_absorpt_T_min   0.831
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8343
_exptl_absorpt_correction_T_max  0.9873
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 0.3
_diffrn_reflns_number            8969
_diffrn_reflns_av_unetI/netI     0.0837
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.428
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_full        24.996
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             4328
_reflns_number_gt                2707
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'bruker smart'
_computing_cell_refinement       'bruker smart'
_computing_data_reduction        'bruker saint'
_computing_structure_solution    'bruker shelxtl'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ORTEP-III
_computing_publication_material  WinGXv1.80.05
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1125P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4328
_refine_ls_number_parameters     343
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1261
_refine_ls_R_factor_gt           0.0743
_refine_ls_wR_factor_ref         0.1963
_refine_ls_wR_factor_gt          0.1738
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8062(9) 0.2259(8) 0.5061(5) 0.0270(18) Uani 1 1 d . . . . .
C2 C 0.7206(10) -0.0911(9) 0.4780(6) 0.036(2) Uani 1 1 d . . . . .
H2 H 0.7500 -0.1454 0.5259 0.043 Uiso 1 1 calc R U . . .
C3 C 0.6569(10) -0.1485(9) 0.4144(6) 0.034(2) Uani 1 1 d . . . . .
C4 C 0.6374(12) -0.2886(9) 0.4211(6) 0.045(2) Uani 1 1 d . . . . .
H4 H 0.6676 -0.3468 0.4672 0.054 Uiso 1 1 calc R U . . .
C5 C 0.5753(10) -0.3391(8) 0.3612(6) 0.038(2) Uani 1 1 d . . . . .
H5 H 0.5644 -0.4322 0.3651 0.045 Uiso 1 1 calc R U . . .
C6 C 0.5272(10) -0.2510(9) 0.2933(6) 0.034(2) Uani 1 1 d . . . . .
C7 C 0.4614(10) -0.2992(9) 0.2288(6) 0.040(2) Uani 1 1 d . . . . .
H7 H 0.4414 -0.3901 0.2341 0.049 Uiso 1 1 calc R U . . .
C8 C 0.4271(10) -0.2125(10) 0.1587(7) 0.047(3) Uani 1 1 d . . . . .
H8 H 0.3834 -0.2443 0.1164 0.056 Uiso 1 1 calc R U . . .
C9 C 0.4576(11) -0.0766(10) 0.1506(7) 0.045(2) Uani 1 1 d . . . . .
H9 H 0.4348 -0.0193 0.1019 0.054 Uiso 1 1 calc R U . . .
C10 C 0.5208(10) -0.0235(9) 0.2122(6) 0.033(2) Uani 1 1 d . . . . .
H10 H 0.5406 0.0676 0.2054 0.039 Uiso 1 1 calc R U . . .
C11 C 0.5541(9) -0.1113(8) 0.2855(6) 0.0301(19) Uani 1 1 d . . . . .
C12 C 1.0246(9) 0.0049(8) 0.2697(5) 0.0260(18) Uani 1 1 d . . . . .
C13 C 0.9748(10) -0.3127(8) 0.2186(6) 0.032(2) Uani 1 1 d . . . . .
H13 H 1.0127 -0.3706 0.2622 0.038 Uiso 1 1 calc R U . . .
C14 C 0.9077(9) -0.3662(8) 0.1553(5) 0.0277(19) Uani 1 1 d . . . . .
C15 C 0.8853(11) -0.5057(8) 0.1623(6) 0.036(2) Uani 1 1 d . . . . .
H15 H 0.9156 -0.5648 0.2080 0.044 Uiso 1 1 calc R U . . .
C16 C 0.8199(11) -0.5543(9) 0.1027(6) 0.040(2) Uani 1 1 d . . . . .
H16 H 0.8032 -0.6462 0.1079 0.048 Uiso 1 1 calc R U . . .
C17 C 0.7774(10) -0.4646(8) 0.0329(6) 0.032(2) Uani 1 1 d . . . . .
C18 C 0.7114(11) -0.5103(9) -0.0321(6) 0.040(2) Uani 1 1 d . . . . .
H18 H 0.6942 -0.6018 -0.0295 0.048 Uiso 1 1 calc R U . . .
C19 C 0.6733(12) -0.4201(10) -0.0983(7) 0.053(3) Uani 1 1 d . . . . .
H19 H 0.6292 -0.4510 -0.1406 0.063 Uiso 1 1 calc R U . . .
C20 C 0.6976(12) -0.2834(9) -0.1052(6) 0.045(2) Uani 1 1 d . . . . .
H20 H 0.6706 -0.2242 -0.1518 0.055 Uiso 1 1 calc R U . . .
C21 C 0.7612(10) -0.2357(8) -0.0433(6) 0.035(2) Uani 1 1 d . . . . .
H21 H 0.7774 -0.1438 -0.0481 0.042 Uiso 1 1 calc R U . . .
C22 C 0.8024(10) -0.3236(8) 0.0273(6) 0.0277(19) Uani 1 1 d . . . . .
N1 N 0.8633(11) 0.2914(8) 0.5608(6) 0.048(2) Uani 1 1 d . . . . .
N2 N 0.7928(8) 0.0945(7) 0.5278(5) 0.0320(17) Uani 1 1 d . . . . .
N3 N 0.7358(8) 0.0366(7) 0.4668(4) 0.0278(15) Uani 1 1 d . . . . .
N4 N 0.6161(8) -0.0604(6) 0.3491(4) 0.0276(16) Uani 1 1 d . . . . .
N5 N 1.0910(9) 0.0687(7) 0.3199(5) 0.0355(18) Uani 1 1 d . . . . .
N6 N 1.0475(8) -0.1302(7) 0.2726(5) 0.0310(16) Uani 1 1 d . . . . .
N7 N 0.9811(8) -0.1835(6) 0.2134(4) 0.0272(15) Uani 1 1 d . . . . .
N8 N 0.8653(7) -0.2746(6) 0.0911(4) 0.0241(15) Uani 1 1 d . . . . .
S1 S 0.7552(3) 0.3177(2) 0.41235(16) 0.0385(6) Uani 1 1 d . . . . .
S2 S 0.9104(3) 0.1053(2) 0.20422(14) 0.0299(5) Uani 1 1 d . . . . .
Cl1 Cl 0.4845(4) 0.2820(3) 0.3099(2) 0.0847(11) Uani 1 1 d . . . . .
Cl2 Cl 0.8101(2) 0.0835(2) 0.01447(14) 0.0316(5) Uani 1 1 d . . . . .
Cu1 Cu 0.66584(12) 0.13822(10) 0.36283(7) 0.0313(3) Uani 1 1 d . . . . .
Cu2 Cu 0.90620(12) -0.07265(9) 0.11432(7) 0.0276(3) Uani 1 1 d . . . . .
O1 O 0.1755(8) 0.3984(6) 0.3613(4) 0.053(2) Uani 1 1 d . . . . .
H1C H 0.2754 0.3949 0.3320 0.080 Uiso 1 1 d . U . . .
H1D H 0.1312 0.3863 0.3195 0.080 Uiso 1 1 d . U . . .
H5A H 1.0846 0.1487 0.3249 0.064 Uiso 1 1 d . U . . .
H1A H 0.8766 0.3749 0.5495 0.064 Uiso 1 1 d . U . . .
H5B H 1.156(12) 0.017(10) 0.350(7) 0.064 Uiso 1 1 d . U . . .
H1B H 0.881(12) 0.244(10) 0.605(7) 0.064 Uiso 1 1 d . U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N2 1.318(10) . ?
C1 N1 1.335(10) . ?
C1 S1 1.733(8) . ?
C2 N3 1.273(10) . ?
C2 C3 1.434(12) . ?
C2 H2 0.9300 . ?
C3 N4 1.339(10) . ?
C3 C4 1.405(11) . ?
C4 C5 1.344(12) . ?
C4 H4 0.9300 . ?
C5 C6 1.395(12) . ?
C5 H5 0.9300 . ?
C6 C7 1.413(12) . ?
C6 C11 1.419(11) . ?
C7 C8 1.366(13) . ?
C7 H7 0.9300 . ?
C8 C9 1.392(13) . ?
C8 H8 0.9300 . ?
C9 C10 1.386(11) . ?
C9 H9 0.9300 . ?
C10 C11 1.405(11) . ?
C10 H10 0.9300 . ?
C11 N4 1.391(10) . ?
C12 N6 1.308(10) . ?
C12 N5 1.330(10) . ?
C12 S2 1.751(8) . ?
C13 N7 1.273(10) . ?
C13 C14 1.431(11) . ?
C13 H13 0.9300 . ?
C14 N8 1.352(9) . ?
C14 C15 1.406(11) . ?
C15 C16 1.353(12) . ?
C15 H15 0.9300 . ?
C16 C17 1.405(11) . ?
C16 H16 0.9300 . ?
C17 C18 1.409(11) . ?
C17 C22 1.428(11) . ?
C18 C19 1.351(12) . ?
C18 H18 0.9300 . ?
C19 C20 1.384(12) . ?
C19 H19 0.9300 . ?
C20 C21 1.365(11) . ?
C20 H20 0.9300 . ?
C21 C22 1.401(11) . ?
C21 H21 0.9300 . ?
C22 N8 1.390(10) . ?
N1 H1A 0.843(8) . ?
N1 H1B 0.82(10) . ?
N2 N3 1.365(9) . ?
N3 Cu1 1.975(6) . ?
N4 Cu1 2.107(6) . ?
N5 H5A 0.787(7) . ?
N5 H5B 0.91(10) . ?
N6 N7 1.377(9) . ?
N7 Cu2 1.972(6) . ?
N8 Cu2 2.146(6) . ?
S1 Cu1 2.304(2) . ?
S2 Cu2 2.303(2) . ?
S2 Cu1 2.715(2) . ?
Cl1 Cu1 2.253(3) . ?
Cl2 Cu2 2.291(2) . ?
Cl2 Cu2 2.691(2) 2_755 ?
Cu2 Cl2 2.691(2) 2_755 ?
O1 H1C 0.869(7) . ?
O1 H1D 0.857(5) . ?

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
N2 C1 N1 116.9(7) . . ?
N2 C1 S1 124.7(6) . . ?
N1 C1 S1 118.5(6) . . ?
N3 C2 C3 118.0(8) . . ?
N3 C2 H2 121.0 . . ?
C3 C2 H2 121.0 . . ?
N4 C3 C4 122.3(8) . . ?
N4 C3 C2 116.0(8) . . ?
C4 C3 C2 121.8(8) . . ?
C5 C4 C3 120.4(8) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 119.7(8) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C5 C6 C7 121.8(8) . . ?
C5 C6 C11 118.8(8) . . ?
C7 C6 C11 119.3(8) . . ?
C8 C7 C6 120.1(8) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C7 C8 C9 119.9(8) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C10 C9 C8 122.5(9) . . ?
C10 C9 H9 118.8 . . ?
C8 C9 H9 118.8 . . ?
C9 C10 C11 118.0(8) . . ?
C9 C10 H10 121.0 . . ?
C11 C10 H10 121.0 . . ?
N4 C11 C10 119.3(7) . . ?
N4 C11 C6 120.5(7) . . ?
C10 C11 C6 120.1(8) . . ?
N6 C12 N5 117.8(7) . . ?
N6 C12 S2 123.6(6) . . ?
N5 C12 S2 118.6(6) . . ?
N7 C13 C14 118.0(7) . . ?
N7 C13 H13 121.0 . . ?
C14 C13 H13 121.0 . . ?
N8 C14 C15 123.0(7) . . ?
N8 C14 C13 116.1(7) . . ?
C15 C14 C13 120.9(7) . . ?
C16 C15 C14 120.1(8) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C17 119.3(8) . . ?
C15 C16 H16 120.4 . . ?
C17 C16 H16 120.4 . . ?
C16 C17 C18 121.7(8) . . ?
C16 C17 C22 119.2(8) . . ?
C18 C17 C22 119.2(8) . . ?
C19 C18 C17 119.4(8) . . ?
C19 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?
C18 C19 C20 122.3(8) . . ?
C18 C19 H19 118.9 . . ?
C20 C19 H19 118.9 . . ?
C21 C20 C19 119.8(8) . . ?
C21 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
C20 C21 C22 120.8(8) . . ?
C20 C21 H21 119.6 . . ?
C22 C21 H21 119.6 . . ?
N8 C22 C21 120.7(7) . . ?
N8 C22 C17 120.7(7) . . ?
C21 C22 C17 118.6(7) . . ?
C1 N1 H1A 121.0(8) . . ?
C1 N1 H1B 114(8) . . ?
H1A N1 H1B 125(8) . . ?
C1 N2 N3 112.3(6) . . ?
C2 N3 N2 119.1(7) . . ?
C2 N3 Cu1 116.1(6) . . ?
N2 N3 Cu1 124.8(5) . . ?
C3 N4 C11 118.2(7) . . ?
C3 N4 Cu1 110.2(5) . . ?
C11 N4 Cu1 131.6(5) . . ?
C12 N5 H5A 127.5(8) . . ?
C12 N5 H5B 118(7) . . ?
H5A N5 H5B 114(7) . . ?
C12 N6 N7 112.1(6) . . ?
C13 N7 N6 118.9(6) . . ?
C13 N7 Cu2 117.3(5) . . ?
N6 N7 Cu2 123.7(5) . . ?
C14 N8 C22 117.6(6) . . ?
C14 N8 Cu2 109.4(5) . . ?
C22 N8 Cu2 132.9(5) . . ?
C1 S1 Cu1 95.8(3) . . ?
C12 S2 Cu2 95.1(3) . . ?
C12 S2 Cu1 89.2(3) . . ?
Cu2 S2 Cu1 114.65(9) . . ?
Cu2 Cl2 Cu2 92.73(8) . 2_755 ?
N3 Cu1 N4 79.7(2) . . ?
N3 Cu1 Cl1 150.6(2) . . ?
N4 Cu1 Cl1 104.0(2) . . ?
N3 Cu1 S1 82.28(19) . . ?
N4 Cu1 S1 161.91(19) . . ?
Cl1 Cu1 S1 92.65(11) . . ?
N3 Cu1 S2 107.9(2) . . ?
N4 Cu1 S2 89.41(18) . . ?
Cl1 Cu1 S2 101.33(11) . . ?
S1 Cu1 S2 94.15(8) . . ?
N7 Cu2 N8 79.1(2) . . ?
N7 Cu2 Cl2 171.20(19) . . ?
N8 Cu2 Cl2 108.59(17) . . ?
N7 Cu2 S2 81.54(19) . . ?
N8 Cu2 S2 155.05(18) . . ?
Cl2 Cu2 S2 89.88(8) . . ?
N7 Cu2 Cl2 96.4(2) . 2_755 ?
N8 Cu2 Cl2 95.69(17) . 2_755 ?
Cl2 Cu2 Cl2 87.27(8) . 2_755 ?
S2 Cu2 Cl2 101.97(8) . 2_755 ?
H1C O1 H1D 105.4(7) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N3 C2 C3 N4 -1.1(13) . . . . ?
N3 C2 C3 C4 179.5(8) . . . . ?
N4 C3 C4 C5 -0.3(15) . . . . ?
C2 C3 C4 C5 179.1(9) . . . . ?
C3 C4 C5 C6 -1.2(15) . . . . ?
C4 C5 C6 C7 179.9(9) . . . . ?
C4 C5 C6 C11 3.8(14) . . . . ?
C5 C6 C7 C8 -174.9(9) . . . . ?
C11 C6 C7 C8 1.2(13) . . . . ?
C6 C7 C8 C9 0.3(14) . . . . ?
C7 C8 C9 C10 -0.8(15) . . . . ?
C8 C9 C10 C11 -0.2(14) . . . . ?
C9 C10 C11 N4 -179.3(8) . . . . ?
C9 C10 C11 C6 1.7(12) . . . . ?
C5 C6 C11 N4 -4.9(13) . . . . ?
C7 C6 C11 N4 178.8(7) . . . . ?
C5 C6 C11 C10 174.0(8) . . . . ?
C7 C6 C11 C10 -2.3(13) . . . . ?
N7 C13 C14 N8 4.0(11) . . . . ?
N7 C13 C14 C15 -174.8(8) . . . . ?
N8 C14 C15 C16 0.5(14) . . . . ?
C13 C14 C15 C16 179.2(8) . . . . ?
C14 C15 C16 C17 1.2(14) . . . . ?
C15 C16 C17 C18 178.9(9) . . . . ?
C15 C16 C17 C22 -0.8(13) . . . . ?
C16 C17 C18 C19 -179.6(9) . . . . ?
C22 C17 C18 C19 0.1(14) . . . . ?
C17 C18 C19 C20 0.4(16) . . . . ?
C18 C19 C20 C21 -0.4(17) . . . . ?
C19 C20 C21 C22 0.0(15) . . . . ?
C20 C21 C22 N8 -179.2(8) . . . . ?
C20 C21 C22 C17 0.4(13) . . . . ?
C16 C17 C22 N8 -1.2(12) . . . . ?
C18 C17 C22 N8 179.2(8) . . . . ?
C16 C17 C22 C21 179.2(8) . . . . ?
C18 C17 C22 C21 -0.4(13) . . . . ?
N1 C1 N2 N3 -179.1(7) . . . . ?
S1 C1 N2 N3 0.9(10) . . . . ?
C3 C2 N3 N2 178.5(7) . . . . ?
C3 C2 N3 Cu1 0.7(11) . . . . ?
C1 N2 N3 C2 178.2(8) . . . . ?
C1 N2 N3 Cu1 -4.1(9) . . . . ?
C4 C3 N4 C11 -0.8(13) . . . . ?
C2 C3 N4 C11 179.8(7) . . . . ?
C4 C3 N4 Cu1 -179.6(7) . . . . ?
C2 C3 N4 Cu1 1.0(10) . . . . ?
C10 C11 N4 C3 -175.5(8) . . . . ?
C6 C11 N4 C3 3.5(12) . . . . ?
C10 C11 N4 Cu1 3.0(11) . . . . ?
C6 C11 N4 Cu1 -178.1(6) . . . . ?
N5 C12 N6 N7 -176.3(7) . . . . ?
S2 C12 N6 N7 4.4(10) . . . . ?
C14 C13 N7 N6 -179.0(7) . . . . ?
C14 C13 N7 Cu2 -2.8(10) . . . . ?
C12 N6 N7 C13 -170.3(7) . . . . ?
C12 N6 N7 Cu2 13.8(9) . . . . ?
C15 C14 N8 C22 -2.5(12) . . . . ?
C13 C14 N8 C22 178.8(7) . . . . ?
C15 C14 N8 Cu2 175.7(7) . . . . ?
C13 C14 N8 Cu2 -3.0(8) . . . . ?
C21 C22 N8 C14 -177.7(7) . . . . ?
C17 C22 N8 C14 2.7(11) . . . . ?
C21 C22 N8 Cu2 4.6(12) . . . . ?
C17 C22 N8 Cu2 -174.9(6) . . . . ?
N2 C1 S1 Cu1 1.8(8) . . . . ?
N1 C1 S1 Cu1 -178.3(7) . . . . ?
N6 C12 S2 Cu2 -15.4(7) . . . . ?
N5 C12 S2 Cu2 165.2(6) . . . . ?
N6 C12 S2 Cu1 99.3(7) . . . . ?
N5 C12 S2 Cu1 -80.1(6) . . . . ?

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
N1 H1A O1 0.843(8) 2.598(7) 3.282(10) 139.1(6) 2_666
N5 H5B N2 0.91(10) 2.17(10) 3.006(10) 153(9) 2_756
N1 H1B N6 0.82(10) 2.26(10) 3.066(10) 172(10) 2_756

_refine_diff_density_max         2.059
_refine_diff_density_min         -0.897
_refine_diff_density_rms         0.161

