# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_1_08SRV373
_database_code_depnum_ccdc_archive 'CCDC 1476704'
_audit_update_record             
;
2016-04-26 deposited with the CCDC.
2016-05-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97


_chemical_formula_moiety         'C13 H13 Cl2 Cu N3 O S'
_chemical_formula_sum            'C13 H13 Cl2 Cu N3 O S'
_chemical_formula_weight         393.76
_chemical_melting_point          ?
_chemical_name_common            ?
_chemical_name_systematic        ?
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'
Cu Cu 0.3201 1.2651 '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'
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_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_angle_alpha                90.77(3)
_cell_angle_beta                 98.75(3)
_cell_angle_gamma                95.52(3)
_cell_formula_units_Z            2
_cell_length_a                   7.7680(16)
_cell_length_b                   9.1578(18)
_cell_length_c                   10.466(2)
_cell_measurement_reflns_used    3454
_cell_measurement_temperature    120.0(2)
_cell_measurement_theta_max      33.10
_cell_measurement_theta_min      1.97
_cell_volume                     732.1(3)
_exptl_absorpt_coefficient_mu    1.999
_exptl_absorpt_correction_T_max  0.9803
_exptl_absorpt_correction_T_min  0.8251
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_F_000             398
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.786
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.01
_exptl_special_details           ?
_diffrn_ambient_temperature      120.0(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Rigaku R-AXIS Spider IP'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0990
_diffrn_reflns_av_sigmaI/netI    0.1020
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9240
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.67
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2382
_reflns_number_total             2846
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    
;
Olex2, Durham University (compiled Sep 8 2008 14:45:24)
;
_computing_publication_material  
;
Olex2, Durham University (compiled Sep 8 2008 14:45:24)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)/Bruker'
_refine_diff_density_max         1.317
_refine_diff_density_min         -0.987
_refine_diff_density_rms         0.155
_refine_ls_R_factor_all          0.1007
_refine_ls_R_factor_gt           0.0864
_refine_ls_extinction_coef       0.032(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2846
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_wR_factor_gt          0.2365
_refine_ls_wR_factor_ref         0.2519
_refine_ls_weighting_details     
;
calc w=1/[σ²(Fo²)+(0.1500P)²+1.0000P] where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_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.
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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 0.17001(11) 0.14299(9) 0.58935(7) 0.0379(4) Uani 1 1 d . . .
Cl1 Cl -0.0115(2) -0.03943(19) 0.65626(16) 0.0404(5) Uani 1 1 d . . .
Cl2 Cl 0.0127(2) 0.32612(19) 0.63466(16) 0.0418(5) Uani 1 1 d . . .
S1 S 0.2163(3) -0.2953(2) 1.03274(17) 0.0472(6) Uani 1 1 d . . .
O1 O 0.3619(6) 0.0293(5) 0.6595(4) 0.0414(12) Uani 1 1 d . . .
N1 N 0.6367(8) 0.0064(7) 0.7609(5) 0.0411(14) Uani 1 1 d . . .
H1 H 0.7477 0.0302 0.7553 0.062 Uiso 1 1 calc R . .
N2 N 0.5968(8) 0.1696(6) 0.5999(5) 0.0346(13) Uani 1 1 d . . .
H2 H 0.7117 0.1861 0.6139 0.052 Uiso 1 1 calc R . .
N3 N 0.3351(8) 0.2648(6) 0.4945(5) 0.0388(13) Uani 1 1 d . . .
C1 C 0.0913(11) -0.3647(9) 0.8815(7) 0.053(2) Uani 1 1 d . . .
H1A H 0.0821 -0.2852 0.8199 0.079 Uiso 1 1 calc R . .
H1B H -0.0261 -0.4037 0.8955 0.079 Uiso 1 1 calc R . .
H1C H 0.1499 -0.4432 0.8468 0.079 Uiso 1 1 calc R . .
C2 C 0.4259(10) -0.2337(8) 0.9907(7) 0.0418(17) Uani 1 1 d . . .
C3 C 0.4385(9) -0.1413(8) 0.8856(6) 0.0370(15) Uani 1 1 d . . .
H3 H 0.3367 -0.1144 0.8324 0.044 Uiso 1 1 calc R . .
C4 C 0.6054(9) -0.0906(7) 0.8620(6) 0.0356(15) Uani 1 1 d . . .
C5 C 0.7555(10) -0.1274(8) 0.9400(6) 0.0405(16) Uani 1 1 d . . .
H5 H 0.8680 -0.0918 0.9220 0.049 Uiso 1 1 calc R . .
C6 C 0.7391(11) -0.2175(8) 1.0453(7) 0.0480(19) Uani 1 1 d . . .
H6 H 0.8408 -0.2418 1.1002 0.058 Uiso 1 1 calc R . .
C7 C 0.5738(11) -0.2716(8) 1.0695(7) 0.0455(18) Uani 1 1 d . . .
H7 H 0.5626 -0.3344 1.1399 0.055 Uiso 1 1 calc R . .
C8 C 0.5239(9) 0.0664(7) 0.6739(6) 0.0356(15) Uani 1 1 d . . .
C9 C 0.5070(9) 0.2525(8) 0.5035(6) 0.0374(15) Uani 1 1 d . . .
C10 C 0.6106(10) 0.3258(8) 0.4188(7) 0.0412(16) Uani 1 1 d . . .
H10 H 0.7317 0.3138 0.4252 0.049 Uiso 1 1 calc R . .
C11 C 0.5321(10) 0.4145(8) 0.3274(6) 0.0416(17) Uani 1 1 d . . .
H11 H 0.5985 0.4662 0.2702 0.050 Uiso 1 1 calc R . .
C12 C 0.3560(10) 0.4274(8) 0.3200(6) 0.0400(16) Uani 1 1 d . . .
H12 H 0.2993 0.4889 0.2580 0.048 Uiso 1 1 calc R . .
C13 C 0.2635(11) 0.3511(8) 0.4024(7) 0.0431(16) Uani 1 1 d . . .
H13 H 0.1414 0.3594 0.3943 0.052 Uiso 1 1 calc R . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix. The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry. An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.957(5) . ?
Cu1 N3 2.004(6) . ?
Cu1 Cl2 2.254(2) . ?
Cu1 Cl1 2.2690(19) . ?
S1 C2 1.792(8) . ?
S1 C1 1.799(7) . ?
O1 C8 1.257(8) . ?
N1 C8 1.328(8) . ?
N1 C4 1.425(8) . ?
N1 H1 0.8800 . ?
N2 C8 1.365(8) . ?
N2 C9 1.411(8) . ?
N2 H2 0.8800 . ?
N3 C9 1.340(10) . ?
N3 C13 1.344(9) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C7 1.385(10) . ?
C2 C3 1.406(9) . ?
C3 C4 1.394(10) . ?
C3 H3 0.9500 . ?
C4 C5 1.390(10) . ?
C5 C6 1.399(9) . ?
C5 H5 0.9500 . ?
C6 C7 1.392(11) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C9 C10 1.419(9) . ?
C10 C11 1.373(10) . ?
C10 H10 0.9500 . ?
C11 C12 1.375(10) . ?
C11 H11 0.9500 . ?
C12 C13 1.362(10) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 N3 89.3(2) . . ?
O1 Cu1 Cl2 143.87(16) . . ?
N3 Cu1 Cl2 96.40(19) . . ?
O1 Cu1 Cl1 86.44(15) . . ?
N3 Cu1 Cl1 165.00(18) . . ?
Cl2 Cu1 Cl1 95.49(7) . . ?
C2 S1 C1 103.6(4) . . ?
C8 O1 Cu1 128.5(4) . . ?
C8 N1 C4 129.9(6) . . ?
C8 N1 H1 115.1 . . ?
C4 N1 H1 115.1 . . ?
C8 N2 C9 126.7(6) . . ?
C8 N2 H2 116.6 . . ?
C9 N2 H2 116.6 . . ?
C9 N3 C13 117.4(6) . . ?
C9 N3 Cu1 125.1(5) . . ?
C13 N3 Cu1 116.9(5) . . ?
S1 C1 H1A 109.5 . . ?
S1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
S1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C7 C2 C3 121.4(7) . . ?
C7 C2 S1 118.1(5) . . ?
C3 C2 S1 120.4(5) . . ?
C4 C3 C2 117.7(6) . . ?
C4 C3 H3 121.2 . . ?
C2 C3 H3 121.2 . . ?
C5 C4 C3 121.8(6) . . ?
C5 C4 N1 114.7(6) . . ?
C3 C4 N1 123.4(6) . . ?
C4 C5 C6 119.3(7) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C7 C6 C5 120.0(7) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C2 C7 C6 119.8(7) . . ?
C2 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
O1 C8 N1 122.3(6) . . ?
O1 C8 N2 122.5(6) . . ?
N1 C8 N2 115.1(6) . . ?
N3 C9 N2 122.1(6) . . ?
N3 C9 C10 121.9(6) . . ?
N2 C9 C10 116.0(6) . . ?
C11 C10 C9 118.6(7) . . ?
C11 C10 H10 120.7 . . ?
C9 C10 H10 120.7 . . ?
C10 C11 C12 119.0(7) . . ?
C10 C11 H11 120.5 . . ?
C12 C11 H11 120.5 . . ?
C13 C12 C11 119.3(7) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
N3 C13 C12 123.8(8) . . ?
N3 C13 H13 118.1 . . ?
C12 C13 H13 118.1 . . ?

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 H1 Cl1 0.88 2.40 3.156(6) 143.7 1_655
N2 H2 Cl2 0.88 2.53 3.371(6) 159.2 1_655

####################################################################### 
# 
# 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_4b_s441
_database_code_depnum_ccdc_archive 'CCDC 1476705'
_audit_update_record             
;
2016-04-26 deposited with the CCDC.
2016-05-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97



_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C13 H13 S O N3), Cu, 2(C F3 S O3)'
_chemical_formula_sum            'C28 H26 Cu F6 N6 O8 S4'
_chemical_formula_weight         880.33

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_H-M   'P 1 21/n 1  '
_symmetry_space_group_name_Hall  '-P 2yn      '
_symmetry_int_tables_number      14

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

_cell_length_a                   12.6428(3)
_cell_length_b                   9.0531(2)
_cell_length_c                   15.2733(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.138(10)
_cell_angle_gamma                90.00
_cell_volume                     1725.94(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    5651
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      30.07

_exptl_crystal_description       plate
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.694
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             894
_exptl_absorpt_coefficient_mu    0.966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS  (Bruker-AXS, 2003)
;
_exptl_absorpt_correction_T_min  0.8767
_exptl_absorpt_correction_T_max  0.9624

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           Mo-K\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART CCD 6000'
_diffrn_measurement_method       '0.30° ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            23373
_diffrn_reflns_av_R_equivalents  0.0524
_diffrn_reflns_av_sigmaI/netI    0.0414
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.95
_diffrn_reflns_theta_max         30.00
_reflns_number_total             5028
_reflns_number_gt                3853
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'SMART Ver. 5.630 (Bruker-AXS, 2003)'
_computing_cell_refinement       'SAINT Ver. 6.45  (Bruker-AXS, 2003)'
_computing_data_reduction        'SAINT Ver. 6.45'
_computing_structure_solution    'SHELXTL Ver. 6.14 (Bruker-AXS, 2003)'
_computing_structure_refinement  'SHELXTL Ver. 6.14'
_computing_molecular_graphics    'SHELXTL Ver. 6.14'
_computing_publication_material  'SHELXTL Ver. 6.14'

_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)+(0.0500P)²+1.5000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5028
_refine_ls_number_parameters     293
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0594
_refine_ls_R_factor_gt           0.0391
_refine_ls_wR_factor_ref         0.1084
_refine_ls_wR_factor_gt          0.0981
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_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
Cu1 Cu 0.0000 0.5000 0.0000 0.01678(9) Uani 1 2 d S . .
S1 S -0.31619(5) 0.71217(7) 0.26698(4) 0.02930(14) Uani 1 1 d . . .
S2 S 0.26469(4) 0.63063(6) 0.12532(4) 0.02260(12) Uani 1 1 d . . .
F1 F 0.40892(15) 0.4929(2) 0.05055(13) 0.0496(5) Uani 1 1 d . . .
F2 F 0.44952(13) 0.5179(2) 0.19151(13) 0.0507(5) Uani 1 1 d . . .
F3 F 0.33255(14) 0.35703(19) 0.13731(15) 0.0527(5) Uani 1 1 d . . .
N1 N 0.04292(15) 0.4262(2) 0.26431(12) 0.0190(3) Uani 1 1 d . . .
N2 N 0.10616(15) 0.2927(2) 0.15651(12) 0.0190(3) Uani 1 1 d . . .
N3 N 0.05504(14) 0.29304(19) 0.00022(11) 0.0179(3) Uani 1 1 d . . .
C1 C -0.3313(2) 0.6637(4) 0.15230(19) 0.0425(7) Uani 1 1 d . . .
C2 C -0.18319(18) 0.6623(2) 0.30946(14) 0.0213(4) Uani 1 1 d . . .
C3 C -0.12186(17) 0.5721(2) 0.26357(14) 0.0192(4) Uani 1 1 d . . .
C4 C -0.01985(17) 0.5291(2) 0.30407(13) 0.0181(4) Uani 1 1 d . . .
C5 C 0.02071(19) 0.5771(3) 0.38930(15) 0.0239(4) Uani 1 1 d . . .
C6 C -0.0416(2) 0.6689(3) 0.43367(15) 0.0282(5) Uani 1 1 d . . .
C7 C -0.1427(2) 0.7122(3) 0.39447(15) 0.0259(5) Uani 1 1 d . . .
C8 C 0.03863(16) 0.4000(2) 0.17779(13) 0.0173(4) Uani 1 1 d . . .
C9 C 0.10391(17) 0.2262(2) 0.07396(14) 0.0187(4) Uani 1 1 d . . .
C10 C 0.15515(19) 0.0889(2) 0.07175(15) 0.0238(4) Uani 1 1 d . . .
C11 C 0.1514(2) 0.0186(2) -0.00869(16) 0.0270(5) Uani 1 1 d . . .
C12 C 0.0968(2) 0.0842(3) -0.08497(16) 0.0267(5) Uani 1 1 d . . .
C13 C 0.05012(18) 0.2197(2) -0.07763(14) 0.0222(4) Uani 1 1 d . . .
C14 C 0.3696(2) 0.4915(3) 0.12574(18) 0.0318(5) Uani 1 1 d . . .
O1 O -0.02420(12) 0.46878(16) 0.12026(9) 0.0189(3) Uani 1 1 d . . .
O2 O 0.18204(13) 0.58475(19) 0.05564(11) 0.0286(4) Uani 1 1 d . . .
O3 O 0.23896(14) 0.6236(2) 0.21343(11) 0.0305(4) Uani 1 1 d . . .
O4 O 0.31783(14) 0.76578(18) 0.10681(11) 0.0281(4) Uani 1 1 d . . .
H1N H 0.087(2) 0.378(3) 0.2966(17) 0.020(6) Uiso 1 1 d . . .
H2N H 0.145(2) 0.260(3) 0.1947(17) 0.016(6) Uiso 1 1 d . . .
H1A H -0.280(3) 0.706(4) 0.125(2) 0.045(9) Uiso 1 1 d . . .
H1B H -0.405(3) 0.708(4) 0.124(2) 0.057(10) Uiso 1 1 d . . .
H1C H -0.328(3) 0.561(4) 0.141(2) 0.045(9) Uiso 1 1 d . . .
H3 H -0.150(2) 0.536(3) 0.2118(18) 0.021(6) Uiso 1 1 d . . .
H5 H 0.086(2) 0.552(3) 0.4140(19) 0.031(7) Uiso 1 1 d . . .
H6 H -0.012(2) 0.711(3) 0.4893(18) 0.028(7) Uiso 1 1 d . . .
H7 H -0.184(2) 0.773(3) 0.426(2) 0.036(8) Uiso 1 1 d . . .
H10 H 0.189(2) 0.050(3) 0.1245(18) 0.023(6) Uiso 1 1 d . . .
H11 H 0.187(2) -0.067(3) -0.0098(19) 0.033(8) Uiso 1 1 d . . .
H12 H 0.087(2) 0.045(3) -0.1408(19) 0.029(7) Uiso 1 1 d . . .
H13 H 0.014(2) 0.270(3) -0.1283(19) 0.031(7) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.9302(14) . yes
Cu1 O1 1.9303(14) 3_565 yes
Cu1 N3 1.9985(17) 3_565 yes
Cu1 N3 1.9985(17) . yes
S1 C2 1.762(2) . yes
S1 C1 1.786(3) . yes
S2 O2 1.4296(16) . yes
S2 O3 1.4353(17) . yes
S2 O4 1.4452(16) . yes
S2 C14 1.828(3) . yes
F1 C14 1.322(3) . yes
F2 C14 1.328(3) . yes
F3 C14 1.327(3) . yes
N1 C8 1.335(3) . yes
N1 C4 1.421(3) . yes
N1 H1N 0.81(3) . ?
N2 C8 1.366(3) . yes
N2 C9 1.394(3) . yes
N2 H2N 0.76(3) . ?
N3 C9 1.340(3) . yes
N3 C13 1.355(3) . yes
C1 H1A 0.91(4) . ?
C1 H1B 1.04(4) . ?
C1 H1C 0.94(4) . ?
C2 C3 1.390(3) . yes
C2 C7 1.393(3) . yes
C3 C4 1.394(3) . yes
C3 H3 0.88(3) . ?
C4 C5 1.391(3) . yes
C5 C6 1.393(3) . yes
C5 H5 0.88(3) . ?
C6 C7 1.380(4) . yes
C6 H6 0.95(3) . ?
C7 H7 0.94(3) . ?
C8 O1 1.253(2) . yes
C9 C10 1.405(3) . yes
C10 C11 1.378(3) . yes
C10 H10 0.92(3) . ?
C11 C12 1.389(3) . yes
C11 H11 0.90(3) . ?
C12 C13 1.374(3) . yes
C12 H12 0.91(3) . ?
C13 H13 0.95(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 O1 180.0 . 3_565 yes
O1 Cu1 N3 91.78(7) . 3_565 yes
O1 Cu1 N3 88.22(7) 3_565 3_565 yes
O1 Cu1 N3 88.22(7) . . yes
O1 Cu1 N3 91.78(6) 3_565 . yes
N3 Cu1 N3 180.0 3_565 . yes
C2 S1 C1 104.18(12) . . yes
O2 S2 O3 115.93(11) . . yes
O2 S2 O4 114.07(10) . . yes
O3 S2 O4 113.75(10) . . yes
O2 S2 C14 104.28(11) . . yes
O3 S2 C14 103.79(12) . . yes
O4 S2 C14 102.95(11) . . yes
C8 N1 C4 127.00(18) . . yes
C8 N1 H1N 115.1(18) . . ?
C4 N1 H1N 117.8(18) . . ?
C8 N2 C9 126.78(18) . . yes
C8 N2 H2N 116.6(19) . . ?
C9 N2 H2N 116.2(19) . . ?
C9 N3 C13 117.85(18) . . yes
C9 N3 Cu1 122.60(14) . . yes
C13 N3 Cu1 119.39(14) . . yes
S1 C1 H1A 112(2) . . ?
S1 C1 H1B 104.8(19) . . ?
H1A C1 H1B 107(3) . . ?
S1 C1 H1C 115(2) . . ?
H1A C1 H1C 106(3) . . ?
H1B C1 H1C 111(3) . . ?
C3 C2 C7 120.6(2) . . yes
C3 C2 S1 122.76(17) . . yes
C7 C2 S1 116.59(17) . . yes
C2 C3 C4 119.42(19) . . yes
C2 C3 H3 120.0(18) . . ?
C4 C3 H3 120.3(18) . . ?
C5 C4 C3 120.4(2) . . yes
C5 C4 N1 117.19(19) . . yes
C3 C4 N1 122.24(18) . . yes
C4 C5 C6 119.3(2) . . yes
C4 C5 H5 120.2(19) . . ?
C6 C5 H5 120.5(19) . . ?
C7 C6 C5 121.0(2) . . yes
C7 C6 H6 118.2(17) . . ?
C5 C6 H6 120.5(17) . . ?
C6 C7 C2 119.3(2) . . yes
C6 C7 H7 119.9(18) . . ?
C2 C7 H7 120.8(18) . . ?
O1 C8 N1 121.83(19) . . yes
O1 C8 N2 122.50(18) . . yes
N1 C8 N2 115.66(18) . . yes
N3 C9 N2 120.39(18) . . yes
N3 C9 C10 122.17(19) . . yes
N2 C9 C10 117.44(19) . . yes
C11 C10 C9 118.6(2) . . yes
C11 C10 H10 123.4(17) . . ?
C9 C10 H10 118.0(17) . . ?
C10 C11 C12 119.5(2) . . yes
C10 C11 H11 118.0(19) . . ?
C12 C11 H11 122.4(19) . . ?
C13 C12 C11 118.4(2) . . yes
C13 C12 H12 115.3(18) . . ?
C11 C12 H12 126.3(18) . . ?
N3 C13 C12 123.3(2) . . yes
N3 C13 H13 115.3(17) . . ?
C12 C13 H13 121.4(17) . . ?
F1 C14 F3 108.3(2) . . yes
F1 C14 F2 108.1(2) . . yes
F3 C14 F2 107.8(2) . . yes
F1 C14 S2 111.31(18) . . yes
F3 C14 S2 111.17(17) . . yes
F2 C14 S2 110.07(19) . . yes
C8 O1 Cu1 124.17(13) . . yes

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 H1N O4 0.81(3) 2.03(3) 2.825(2) 171(3) 2_545
N2 H2N O3 0.76(3) 2.23(3) 2.982(3) 168(3) 2_545

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.418
_refine_diff_density_min         -0.634
_refine_diff_density_rms         0.083

# File processed with modiCIFer Dec. 16,2005. I.A.Guzei, UW-Madison.
####################################################################### 
# 
# 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_LHBF4_ns4
_database_code_depnum_ccdc_archive 'CCDC 1476706'
_audit_update_record             
;
2016-04-26 deposited with the CCDC.
2016-05-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97

_chemical_formula_moiety         'C13 H14 N3 O S, B F4'
_chemical_formula_sum            'C13 H14 B F4 N3 O S'
_chemical_formula_weight         347.14
_chemical_melting_point          ?
_chemical_name_common            ?
_chemical_name_systematic        ?
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'
B B 0.0013 0.0007 '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'
O O 0.0106 0.0060 '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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_angle_alpha                96.700(10)
_cell_angle_beta                 92.305(10)
_cell_angle_gamma                99.927(10)
_cell_formula_units_Z            2
_cell_length_a                   6.6282(3)
_cell_length_b                   10.3741(5)
_cell_length_c                   11.1178(5)
_cell_measurement_reflns_used    2082
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.342
_cell_measurement_theta_min      2.554
_cell_volume                     746.47(6)
_exptl_absorpt_coefficient_mu    0.266
_exptl_absorpt_correction_T_max  0.9703
_exptl_absorpt_correction_T_min  0.27
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 SADABS-2006/1 (Bruker,2006) was used for absorption correction.
 R(int) was 0.0582 before and 0.0279 after correction.
 The Ratio of minimum to maximum transmission is 0.278264454292.
 The λ/2 correction factor is 0.0015
;
_exptl_crystal_F_000             356
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.544
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_special_details           ?
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART CCD 6000'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           'MO K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_av_sigmaI/netI    0.0576
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9369
_diffrn_reflns_theta_full        29.00
_diffrn_reflns_theta_max         29.00
_diffrn_reflns_theta_min         1.85
_diffrn_source_current           35.0
_diffrn_source_power             1.75
_diffrn_source_voltage           50.0
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2553
_reflns_number_total             3948
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        'SAINT v6.45A (Bruker, 2003)'
_computing_molecular_graphics    
;
Olex2, Durham University (compiled Sep 8 2008 14:45:24)
;
_computing_publication_material  
;
Olex2, Durham University (compiled Sep 8 2008 14:45:24)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)/Bruker'
_refine_diff_density_max         0.441
_refine_diff_density_min         -0.458
_refine_diff_density_rms         0.065
_refine_ls_R_factor_all          0.0854
_refine_ls_R_factor_gt           0.0479
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3948
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.099
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_wR_factor_gt          0.1152
_refine_ls_wR_factor_ref         0.1324
_refine_ls_weighting_details     
;
calc w=1/[σ²(Fo²)+(0.0600P)²+0.0000P] where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_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.
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
S1 S 0.23125(11) 0.53170(6) 0.38488(5) 0.03961(19) Uani 1 1 d . . .
O1 O 0.2814(2) -0.10780(14) 0.49772(12) 0.0264(3) Uani 1 1 d . . .
N1 N 0.2408(3) 0.10509(17) 0.55939(15) 0.0236(4) Uani 1 1 d . . .
N2 N 0.2994(3) -0.02869(18) 0.69983(15) 0.0232(4) Uani 1 1 d . . .
N3 N 0.2889(3) -0.25725(17) 0.67444(16) 0.0247(4) Uani 1 1 d . . .
C1 C 0.2603(4) 0.5869(3) 0.2383(2) 0.0386(6) Uani 1 1 d . . .
C2 C 0.2269(3) 0.3603(2) 0.35769(18) 0.0255(4) Uani 1 1 d . . .
C3 C 0.2351(3) 0.2948(2) 0.45997(18) 0.0246(4) Uani 1 1 d . . .
C4 C 0.2304(3) 0.1594(2) 0.44855(17) 0.0223(4) Uani 1 1 d . . .
C5 C 0.2125(3) 0.0858(2) 0.33435(18) 0.0243(4) Uani 1 1 d . . .
C6 C 0.2054(3) 0.1526(2) 0.23324(18) 0.0258(4) Uani 1 1 d . . .
C7 C 0.2127(3) 0.2876(2) 0.24287(18) 0.0267(5) Uani 1 1 d . . .
C8 C 0.2740(3) -0.0163(2) 0.57647(18) 0.0225(4) Uani 1 1 d . . .
C9 C 0.2961(3) -0.1441(2) 0.74799(18) 0.0219(4) Uani 1 1 d . . .
C10 C 0.3000(3) -0.1472(2) 0.87325(19) 0.0253(4) Uani 1 1 d . . .
C11 C 0.2933(3) -0.2652(2) 0.9177(2) 0.0279(5) Uani 1 1 d . . .
C12 C 0.2840(3) -0.3811(2) 0.8388(2) 0.0296(5) Uani 1 1 d . . .
C13 C 0.2821(3) -0.3747(2) 0.7177(2) 0.0290(5) Uani 1 1 d . . .
F1 F -0.0278(3) 0.16572(16) 0.87099(16) 0.0613(5) Uani 1 1 d . . .
F2 F 0.1890(2) 0.29091(14) 0.76315(11) 0.0432(4) Uani 1 1 d . . .
F3 F 0.1741(3) 0.35151(13) 0.96417(12) 0.0511(4) Uani 1 1 d . . .
F4 F 0.3139(3) 0.17229(15) 0.89614(14) 0.0551(5) Uani 1 1 d . . .
B1 B 0.1606(5) 0.2459(3) 0.8762(2) 0.0336(6) Uani 1 1 d . . .
H1N H 0.228(4) 0.162(2) 0.625(2) 0.031(6) Uiso 1 1 d . . .
H2N H 0.301(4) 0.038(2) 0.750(2) 0.028(6) Uiso 1 1 d . . .
H3N H 0.296(4) -0.245(3) 0.595(3) 0.043(7) Uiso 1 1 d . . .
H1A H 0.395(5) 0.564(3) 0.206(3) 0.055(8) Uiso 1 1 d . . .
H1B H 0.143(4) 0.543(3) 0.178(3) 0.050(8) Uiso 1 1 d . . .
H1C H 0.257(5) 0.681(3) 0.253(3) 0.069(10) Uiso 1 1 d . . .
H3 H 0.252(4) 0.343(3) 0.542(3) 0.042(7) Uiso 1 1 d . . .
H5 H 0.211(3) -0.008(2) 0.323(2) 0.022(6) Uiso 1 1 d . . .
H6 H 0.197(3) 0.102(2) 0.152(2) 0.028(6) Uiso 1 1 d . . .
H7 H 0.213(3) 0.332(2) 0.172(2) 0.027(6) Uiso 1 1 d . . .
H10 H 0.307(4) -0.065(2) 0.924(2) 0.032(6) Uiso 1 1 d . . .
H11 H 0.282(4) -0.267(2) 1.005(2) 0.039(7) Uiso 1 1 d . . .
H12 H 0.283(4) -0.464(3) 0.868(2) 0.039(7) Uiso 1 1 d . . .
H13 H 0.273(3) -0.452(2) 0.656(2) 0.030(6) Uiso 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
S1 C2 1.764(2) . ?
S1 C1 1.796(2) . ?
O1 C8 1.223(2) . ?
N1 C8 1.349(3) . ?
N1 C4 1.418(2) . ?
N1 H1N 0.90(3) . ?
N2 C9 1.365(3) . ?
N2 C8 1.399(2) . ?
N2 H2N 0.84(3) . ?
N3 C9 1.343(3) . ?
N3 C13 1.356(3) . ?
N3 H3N 0.91(3) . ?
C1 H1A 1.03(3) . ?
C1 H1B 1.01(3) . ?
C1 H1C 0.98(3) . ?
C2 C3 1.395(3) . ?
C2 C7 1.396(3) . ?
C3 C4 1.390(3) . ?
C3 H3 0.98(3) . ?
C4 C5 1.393(3) . ?
C5 C6 1.392(3) . ?
C5 H5 0.97(2) . ?
C6 C7 1.384(3) . ?
C6 H6 0.98(2) . ?
C7 H7 0.96(2) . ?
C9 C10 1.396(3) . ?
C10 C11 1.367(3) . ?
C10 H10 0.96(2) . ?
C11 C12 1.394(3) . ?
C11 H11 0.98(3) . ?
C12 C13 1.355(3) . ?
C12 H12 0.95(3) . ?
C13 H13 0.98(2) . ?
F1 B1 1.371(3) . ?
F2 B1 1.400(3) . ?
F3 B1 1.369(3) . ?
F4 B1 1.397(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 S1 C1 104.40(12) . . ?
C8 N1 C4 128.02(17) . . ?
C8 N1 H1N 118.0(16) . . ?
C4 N1 H1N 114.0(16) . . ?
C9 N2 C8 125.78(19) . . ?
C9 N2 H2N 115.7(17) . . ?
C8 N2 H2N 118.0(17) . . ?
C9 N3 C13 122.17(19) . . ?
C9 N3 H3N 113.0(16) . . ?
C13 N3 H3N 124.7(16) . . ?
S1 C1 H1A 108.4(16) . . ?
S1 C1 H1B 112.1(16) . . ?
H1A C1 H1B 109(2) . . ?
S1 C1 H1C 104(2) . . ?
H1A C1 H1C 115(3) . . ?
H1B C1 H1C 109(2) . . ?
C3 C2 C7 118.9(2) . . ?
C3 C2 S1 116.31(16) . . ?
C7 C2 S1 124.75(16) . . ?
C4 C3 C2 120.90(19) . . ?
C4 C3 H3 117.5(16) . . ?
C2 C3 H3 121.5(16) . . ?
C3 C4 C5 120.53(18) . . ?
C3 C4 N1 115.29(17) . . ?
C5 C4 N1 124.16(19) . . ?
C6 C5 C4 117.8(2) . . ?
C6 C5 H5 119.2(13) . . ?
C4 C5 H5 122.9(13) . . ?
C7 C6 C5 122.40(19) . . ?
C7 C6 H6 119.1(14) . . ?
C5 C6 H6 118.5(14) . . ?
C6 C7 C2 119.38(18) . . ?
C6 C7 H7 121.2(14) . . ?
C2 C7 H7 119.4(14) . . ?
O1 C8 N1 126.74(19) . . ?
O1 C8 N2 121.74(19) . . ?
N1 C8 N2 111.52(18) . . ?
N3 C9 N2 119.92(18) . . ?
N3 C9 C10 118.91(18) . . ?
N2 C9 C10 121.17(19) . . ?
C11 C10 C9 119.3(2) . . ?
C11 C10 H10 123.5(14) . . ?
C9 C10 H10 117.2(14) . . ?
C10 C11 C12 120.3(2) . . ?
C10 C11 H11 118.4(15) . . ?
C12 C11 H11 121.1(14) . . ?
C13 C12 C11 119.0(2) . . ?
C13 C12 H12 119.6(16) . . ?
C11 C12 H12 121.4(16) . . ?
C12 C13 N3 120.3(2) . . ?
C12 C13 H13 123.7(14) . . ?
N3 C13 H13 115.9(14) . . ?
F3 B1 F1 111.2(2) . . ?
F3 B1 F4 111.2(2) . . ?
F1 B1 F4 109.4(2) . . ?
F3 B1 F2 109.47(19) . . ?
F1 B1 F2 108.4(2) . . ?
F4 B1 F2 107.1(2) . . ?

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 H1N F2 0.90(3) 1.97(3) 2.870(2) 176(2) .
N2 H2N F4 0.84(3) 2.00(3) 2.824(2) 168(2) .
N3 H3N O1 0.91(3) 1.90(3) 2.645(2) 138(2) .

####################################################################### 
# 
# 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_4A_nas1
_database_code_depnum_ccdc_archive 'CCDC 1476707'
_audit_update_record             
;
2016-04-26 deposited with the CCDC.
2016-05-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97




_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H26 Cu N6 O2 S2, 2 C F3 O3 S'
_chemical_formula_sum            'C28 H26 Cu F6 N6 O8 S4'
_chemical_formula_weight         880.33

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'
F F 0.0171 0.0103 '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'
S S 0.1246 0.1234 '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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1        '
_symmetry_space_group_name_Hall  '-P 1        '
_symmetry_int_tables_number      2

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

_cell_length_a                   8.2365(3)
_cell_length_b                   9.6360(3)
_cell_length_c                   11.5943(4)
_cell_angle_alpha                110.59(2)
_cell_angle_beta                 97.00(2)
_cell_angle_gamma                103.85(2)
_cell_volume                     814.57(5)
_cell_formula_units_Z            1
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    999
_cell_measurement_theta_min      1.93
_cell_measurement_theta_max      30.00

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.795
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             447
_exptl_absorpt_coefficient_mu    1.023
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS  (Bruker-AXS, 2003)
;
_exptl_absorpt_correction_T_min  0.7913
_exptl_absorpt_correction_T_max  0.9700

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           Mo-K\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART CCD 6000'
_diffrn_measurement_method       '0.30° ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10725
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_av_sigmaI/netI    0.0532
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.93
_diffrn_reflns_theta_max         30.00
_reflns_number_total             4645
_reflns_number_gt                3647
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'SMART Ver. 5.630 (Bruker-AXS, 2003)'
_computing_cell_refinement       'SAINT Ver. 6.45  (Bruker-AXS, 2003)'
_computing_data_reduction        'SAINT Ver. 6.45'
_computing_structure_solution    'SHELXTL Ver. 6.14 (Bruker-AXS, 2003)'
_computing_structure_refinement  'SHELXTL Ver. 6.14'
_computing_molecular_graphics    'SHELXTL Ver. 6.14'
_computing_publication_material  'SHELXTL Ver. 6.14'

_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.

 The analysis of collected data have shown that the crystal was twinned
 and the reflections with H = 3 and 5 were severely ovrlapped. After
 numerous failed attempts to find a twinnig low and not being able
 to find a crystal of better quality, the reflections with H=3,5 have
 been removed from the final refinement.  

;

_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)+(0.0400P)²+10.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4645
_refine_ls_number_parameters     242
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0804
_refine_ls_R_factor_gt           0.0641
_refine_ls_wR_factor_ref         0.1662
_refine_ls_wR_factor_gt          0.1579
_refine_ls_goodness_of_fit_ref   0.874
_refine_ls_restrained_S_all      0.874
_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
Cu1 Cu 0.0000 1.0000 0.0000 0.01373(16) Uani 1 2 d S . .
S1 S 0.78135(13) 0.80416(13) 0.42338(11) 0.0212(2) Uani 1 1 d . . .
S2 S 0.03450(13) 1.41290(11) 0.17726(10) 0.0174(2) Uani 1 1 d . . .
F1 F 0.0047(4) 1.3477(4) 0.3766(3) 0.0377(8) Uani 1 1 d . . .
F2 F 0.2414(4) 1.3375(4) 0.3171(3) 0.0391(8) Uani 1 1 d . . .
F3 F 0.2039(4) 1.5580(3) 0.4127(3) 0.0317(7) Uani 1 1 d . . .
O1 O 0.1176(4) 0.9905(3) 0.1529(3) 0.0163(5) Uani 1 1 d . . .
O2 O -0.0583(4) 1.2505(3) 0.1016(3) 0.0209(6) Uani 1 1 d . . .
O3 O 0.1834(4) 1.4774(4) 0.1380(3) 0.0284(7) Uani 1 1 d . . .
O4 O -0.0734(5) 1.5122(4) 0.2113(3) 0.0274(7) Uani 1 1 d . . .
N1 N 0.1905(4) 0.8492(4) 0.2614(4) 0.0187(7) Uani 1 1 d . . .
H1 H 0.1478 0.7757 0.2875 0.028 Uiso 1 1 calc R . .
N2 N -0.0828(4) 0.7751(4) 0.1476(3) 0.0163(6) Uani 1 1 d . . .
H2 H -0.0947 0.6943 0.1684 0.024 Uiso 1 1 calc R . .
N3 N -0.2197(4) 0.8781(4) 0.0197(3) 0.0150(6) Uani 1 1 d . . .
C1 C 0.6415(6) 0.6093(5) 0.3741(5) 0.0263(9) Uani 1 1 d . . .
H1B H 0.7099 0.5406 0.3799 0.039 Uiso 1 1 calc R . .
H1A H 0.5782 0.5730 0.2864 0.039 Uiso 1 1 calc R . .
H1C H 0.5602 0.6080 0.4291 0.039 Uiso 1 1 calc R . .
C2 C 0.6461(5) 0.9021(5) 0.3785(4) 0.0168(7) Uani 1 1 d . . .
C3 C 0.4687(5) 0.8379(5) 0.3365(4) 0.0176(7) Uani 1 1 d . . .
H3 H 0.4146 0.7355 0.3294 0.026 Uiso 1 1 calc R . .
C4 C 0.3709(5) 0.9242(5) 0.3048(4) 0.0153(7) Uani 1 1 d . . .
C5 C 0.4471(5) 1.0758(5) 0.3183(4) 0.0187(8) Uani 1 1 d . . .
H5 H 0.3795 1.1369 0.3020 0.028 Uiso 1 1 calc R . .
C6 C 0.6257(5) 1.1361(5) 0.3566(4) 0.0196(8) Uani 1 1 d . . .
H6 H 0.6803 1.2377 0.3622 0.029 Uiso 1 1 calc R . .
C7 C 0.7246(5) 1.0511(5) 0.3863(4) 0.0207(8) Uani 1 1 d . . .
H7 H 0.8460 1.0942 0.4120 0.031 Uiso 1 1 calc R . .
C8 C 0.0773(5) 0.8777(4) 0.1848(4) 0.0141(7) Uani 1 1 d . . .
C9 C -0.2291(5) 0.7821(5) 0.0810(4) 0.0155(7) Uani 1 1 d . . .
C10 C -0.3727(4) 0.6850(4) 0.0841(3) 0.0108(6) Uani 1 1 d . . .
H10 H -0.3699 0.6189 0.1284 0.016 Uiso 1 1 calc R . .
C11 C -0.5201(5) 0.6849(5) 0.0225(4) 0.0190(8) Uani 1 1 d . . .
H11 H -0.6244 0.6158 0.0220 0.029 Uiso 1 1 calc R . .
C12 C -0.5266(5) 0.7820(5) -0.0408(4) 0.0203(8) Uani 1 1 d . . .
H12 H -0.6324 0.7826 -0.0834 0.030 Uiso 1 1 calc R . .
C13 C -0.3723(5) 0.8774(5) -0.0387(4) 0.0190(8) Uani 1 1 d . . .
H13 H -0.3727 0.9465 -0.0803 0.028 Uiso 1 1 calc R . .
C14 C 0.1245(6) 1.4119(5) 0.3283(4) 0.0215(8) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.956(3) 2_575 yes
Cu1 O1 1.956(3) . yes
Cu1 N3 1.994(3) . yes
Cu1 N3 1.994(3) 2_575 yes
S1 C2 1.764(4) . yes
S1 C1 1.797(5) . yes
S2 O3 1.438(3) . yes
S2 O4 1.445(3) . yes
S2 O2 1.449(3) . yes
S2 C14 1.820(5) . yes
F1 C14 1.326(5) . yes
F2 C14 1.324(5) . yes
F3 C14 1.342(5) . yes
O1 C8 1.252(5) . yes
N1 C8 1.351(5) . yes
N1 C4 1.425(5) . yes
N1 H1 0.8800 . ?
N2 C8 1.356(5) . yes
N2 C9 1.379(5) . yes
N2 H2 0.8800 . ?
N3 C9 1.344(5) . yes
N3 C13 1.351(5) . yes
C1 H1B 0.9800 . ?
C1 H1A 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.391(5) . yes
C2 C7 1.392(6) . yes
C3 C4 1.392(6) . yes
C3 H3 0.9500 . ?
C4 C5 1.389(5) . yes
C5 C6 1.396(6) . yes
C5 H5 0.9500 . ?
C6 C7 1.378(6) . yes
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C9 C10 1.335(5) . yes
C10 C11 1.331(5) . yes
C10 H10 0.9500 . ?
C11 C12 1.384(6) . yes
C11 H11 0.9500 . ?
C12 C13 1.371(6) . yes
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O1 180.00(17) 2_575 . yes
O1 Cu1 N3 91.41(13) 2_575 . yes
O1 Cu1 N3 88.59(13) . . yes
O1 Cu1 N3 88.59(13) 2_575 2_575 yes
O1 Cu1 N3 91.41(13) . 2_575 yes
N3 Cu1 N3 180.0 . 2_575 yes
C2 S1 C1 103.5(2) . . yes
O3 S2 O4 114.6(2) . . yes
O3 S2 O2 115.8(2) . . yes
O4 S2 O2 114.5(2) . . yes
O3 S2 C14 103.4(2) . . yes
O4 S2 C14 102.8(2) . . yes
O2 S2 C14 103.34(19) . . yes
C8 O1 Cu1 124.7(3) . . yes
C8 N1 C4 127.6(3) . . yes
C8 N1 H1 116.2 . . ?
C4 N1 H1 116.2 . . ?
C8 N2 C9 127.7(3) . . yes
C8 N2 H2 116.1 . . ?
C9 N2 H2 116.1 . . ?
C9 N3 C13 115.2(3) . . yes
C9 N3 Cu1 123.8(3) . . yes
C13 N3 Cu1 120.8(3) . . yes
S1 C1 H1B 109.5 . . ?
S1 C1 H1A 109.5 . . ?
H1B C1 H1A 109.5 . . ?
S1 C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
C3 C2 C7 119.7(4) . . yes
C3 C2 S1 123.4(3) . . yes
C7 C2 S1 116.9(3) . . yes
C2 C3 C4 119.8(4) . . yes
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 121.0(4) . . yes
C5 C4 N1 122.8(4) . . yes
C3 C4 N1 116.2(3) . . yes
C4 C5 C6 118.2(4) . . yes
C4 C5 H5 120.9 . . ?
C6 C5 H5 120.9 . . ?
C7 C6 C5 121.4(4) . . yes
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C6 C7 C2 119.9(4) . . yes
C6 C7 H7 120.1 . . ?
C2 C7 H7 120.1 . . ?
O1 C8 N1 122.5(4) . . yes
O1 C8 N2 123.5(4) . . yes
N1 C8 N2 114.1(3) . . yes
C10 C9 N3 125.9(4) . . yes
C10 C9 N2 113.1(3) . . yes
N3 C9 N2 121.0(3) . . yes
C11 C10 C9 117.0(4) . . yes
C11 C10 H10 121.5 . . ?
C9 C10 H10 121.5 . . ?
C10 C11 C12 122.2(4) . . yes
C10 C11 H11 118.9 . . ?
C12 C11 H11 118.9 . . ?
C13 C12 C11 116.4(4) . . yes
C13 C12 H12 121.8 . . ?
C11 C12 H12 121.8 . . ?
N3 C13 C12 123.2(4) . . yes
N3 C13 H13 118.4 . . ?
C12 C13 H13 118.4 . . ?
F2 C14 F1 109.0(4) . . yes
F2 C14 F3 106.7(4) . . yes
F1 C14 F3 107.3(4) . . yes
F2 C14 S2 111.2(3) . . yes
F1 C14 S2 112.1(3) . . yes
F3 C14 S2 110.3(3) . . yes

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 H1 O4 0.88 2.52 3.255(5) 141.1 1_545
N2 H2 O4 0.88 2.02 2.892(5) 168.4 1_545

_diffrn_measured_fraction_theta_max 0.975
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.975
_refine_diff_density_max         2.150
_refine_diff_density_min         -0.911
_refine_diff_density_rms         0.149

# File processed with modiCIFer Dec. 16,2005. I.A.Guzei, UW-Madison.

####################################################################### 
# 
# 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_3_NAS3
_database_code_depnum_ccdc_archive 'CCDC 1476708'
_audit_update_record             
;
2016-04-26 deposited with the CCDC.
2016-05-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H26 Cu N8 O8 S2'
_chemical_formula_weight         706.21
_chemical_melting_point          ?
_chemical_name_common            ?
_chemical_name_systematic        ?
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'
Cu Cu 0.3201 1.2651 '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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/c
_symmetry_space_group_name_Hall  '-P 2ybc'
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_angle_alpha                90.00
_cell_angle_beta                 98.900(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.9556(3)
_cell_length_b                   21.6859(9)
_cell_length_c                   7.1433(4)
_cell_measurement_reflns_used    2634
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.537
_cell_measurement_theta_min      2.302
_cell_volume                     1370.60(11)
_exptl_absorpt_coefficient_mu    1.018
_exptl_absorpt_correction_T_max  0.9701
_exptl_absorpt_correction_T_min  0.8706
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2006/1 (Bruker,2006)'
_exptl_crystal_F_000             726
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.711
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.03
_exptl_special_details           ?
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'BRUKER SMART 6000 CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           'MO K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0534
_diffrn_reflns_av_sigmaI/netI    0.0465
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            13846
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         1.88
_diffrn_source_current           35.0
_diffrn_source_power             1.75
_diffrn_source_voltage           50.0
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2379
_reflns_number_total             3301
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'SAINT v6.45A (Bruker, 2003)'
_computing_data_collection       'SMART v5.625 (Bruker, 2001)'
_computing_data_reduction        'SAINT v6.45A (Bruker, 2003)'
_computing_molecular_graphics    
;
Olex2, Durham University (compiled Jul 18 2008 15:30:44)
;
_computing_publication_material  
;
Olex2, Durham University (compiled Jul 18 2008 15:30:44)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)/Bruker'
_refine_diff_density_max         0.649
_refine_diff_density_min         -0.942
_refine_diff_density_rms         0.095
_refine_ls_R_factor_all          0.0691
_refine_ls_R_factor_gt           0.0405
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3301
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_wR_factor_gt          0.0938
_refine_ls_wR_factor_ref         0.1069
_refine_ls_weighting_details     
;
calc w=1/[σ²(Fo²)+(0.0400P)²+2.0000P] where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_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.
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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 0.5000 0.5000 0.5000 0.01566(13) Uani 1 2 d S . .
S1 S -0.09201(8) 0.65637(3) 0.14817(12) 0.02399(18) Uani 1 1 d . . .
O1 O 0.4535(2) 0.56823(9) 0.3207(3) 0.0184(4) Uani 1 1 d . A .
O2 O 0.6485(2) 0.56395(9) 0.7332(3) 0.0216(4) Uani 1 1 d . A .
O3 O 0.7339(2) 0.62862(11) 0.5414(3) 0.0282(5) Uani 1 1 d . A .
O4 O 0.6043(3) 0.66210(10) 0.7523(3) 0.0279(5) Uani 1 1 d . A .
N1 N 0.4580(3) 0.62538(11) 0.0548(4) 0.0190(5) Uani 1 1 d . A .
N2 N 0.6235(3) 0.54630(11) 0.1178(4) 0.0170(5) Uani 1 1 d . A .
N3 N 0.6894(3) 0.48207(10) 0.3859(3) 0.0131(5) Uani 0.70 1 d P A 1
C10 C 0.8423(3) 0.49281(11) 0.1432(3) 0.0129(5) Uani 0.70 1 d P A 1
H10 H 0.8551 0.5098 0.0242 0.019 Uiso 1 1 calc R A 1
N4 N 0.6635(3) 0.61927(11) 0.6735(4) 0.0185(5) Uani 1 1 d . . .
C1 C -0.2013(4) 0.72145(15) 0.2011(5) 0.0240(7) Uani 1 1 d . . .
C2 C 0.0836(3) 0.68881(13) 0.1203(4) 0.0176(6) Uani 1 1 d . . .
C3 C 0.1984(3) 0.64666(13) 0.1015(4) 0.0179(6) Uani 1 1 d . . .
C4 C 0.3408(3) 0.66762(13) 0.0807(4) 0.0173(6) Uani 1 1 d . . .
C5 C 0.3715(3) 0.73056(14) 0.0748(4) 0.0203(6) Uani 1 1 d . . .
C6 C 0.2562(3) 0.77192(14) 0.0920(4) 0.0224(6) Uani 1 1 d . . .
C7 C 0.1132(3) 0.75185(13) 0.1149(4) 0.0199(6) Uani 1 1 d . . .
C8 C 0.5078(3) 0.57952(12) 0.1742(4) 0.0160(5) Uani 1 1 d . . .
C9 C 0.7206(3) 0.50550(12) 0.2227(4) 0.0156(5) Uani 1 1 d . . .
C10A C 0.6894(3) 0.48207(10) 0.3859(3) 0.0131(5) Uani 0.30 1 d P A 2
N3A N 0.8423(3) 0.49281(11) 0.1432(3) 0.0129(5) Uani 0.30 1 d P A 2
C11 C 0.9449(3) 0.45532(14) 0.2376(5) 0.0213(6) Uani 1 1 d . . .
C12 C 0.9274(3) 0.43002(14) 0.4110(5) 0.0218(6) Uani 1 1 d . A .
C13 C 0.7971(3) 0.44434(14) 0.4786(5) 0.0205(6) Uani 1 1 d . . .
H1A H -0.291(4) 0.7079(16) 0.253(5) 0.027(9) Uiso 1 1 d . . .
H1B H -0.238(4) 0.7480(18) 0.082(5) 0.036(10) Uiso 1 1 d . . .
H1C H -0.139(4) 0.7490(18) 0.294(5) 0.034(10) Uiso 1 1 d . . .
H1N H 0.511(4) 0.6340(17) -0.033(5) 0.024(9) Uiso 1 1 d . . .
H2N H 0.648(4) 0.5534(16) 0.008(5) 0.026(9) Uiso 1 1 d . . .
H3 H 0.183(4) 0.6050(16) 0.101(5) 0.023(9) Uiso 1 1 d . . .
H5 H 0.468(4) 0.7461(15) 0.064(5) 0.019(8) Uiso 1 1 d . . .
H6 H 0.273(4) 0.8180(17) 0.095(5) 0.030(9) Uiso 1 1 d . . .
H7 H 0.037(4) 0.7820(17) 0.124(5) 0.031(10) Uiso 1 1 d . . .
H11 H 1.025(4) 0.4484(15) 0.189(5) 0.022(9) Uiso 1 1 d . . .
H12 H 0.998(4) 0.4071(16) 0.479(5) 0.023(9) Uiso 1 1 d . . .
H13 H 0.777(4) 0.4302(18) 0.594(6) 0.037(10) Uiso 1 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix. The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry. An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.9592(19) . ?
Cu1 O1 1.9592(19) 3_666 ?
Cu1 C10A 2.030(2) 3_666 ?
Cu1 N3 2.030(2) 3_666 ?
Cu1 N3 2.030(2) . ?
Cu1 O2 2.404(2) . ?
Cu1 O2 2.404(2) 3_666 ?
S1 C2 1.762(3) . ?
S1 C1 1.791(3) . ?
O1 C8 1.244(3) . ?
O2 N4 1.287(3) . ?
O3 N4 1.230(3) . ?
O4 N4 1.246(3) . ?
N1 C8 1.341(4) . ?
N1 C4 1.427(4) . ?
N1 H1N 0.86(4) . ?
N2 C8 1.373(3) . ?
N2 C9 1.378(3) . ?
N2 H2N 0.86(4) . ?
N3 C9 1.340(4) . ?
N3 C13 1.357(4) . ?
C10 C11 1.330(4) . ?
C10 C9 1.333(4) . ?
C10 H10 0.9500 . ?
C1 H1A 0.98(4) . ?
C1 H1B 1.04(4) . ?
C1 H1C 1.00(4) . ?
C2 C7 1.394(4) . ?
C2 C3 1.398(4) . ?
C3 C4 1.383(4) . ?
C3 H3 0.91(3) . ?
C4 C5 1.394(4) . ?
C5 C6 1.388(4) . ?
C5 H5 0.94(3) . ?
C6 C7 1.386(4) . ?
C6 H6 1.01(4) . ?
C7 H7 0.96(4) . ?
C11 C12 1.385(4) . ?
C11 H11 0.86(3) . ?
C12 C13 1.366(4) . ?
C12 H12 0.88(3) . ?
C13 H13 0.92(4) . ?

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 O1 180.00(11) . 3_666 ?
O1 Cu1 C10A 90.67(9) . 3_666 ?
O1 Cu1 C10A 89.33(9) 3_666 3_666 ?
O1 Cu1 N3 90.67(9) . 3_666 ?
O1 Cu1 N3 89.33(9) 3_666 3_666 ?
C10A Cu1 N3 0.00(6) 3_666 3_666 ?
O1 Cu1 N3 89.33(9) . . ?
O1 Cu1 N3 90.67(9) 3_666 . ?
C10A Cu1 N3 180.0 3_666 . ?
N3 Cu1 N3 180.0 3_666 . ?
O1 Cu1 O2 93.22(8) . . ?
O1 Cu1 O2 86.78(8) 3_666 . ?
C10A Cu1 O2 91.06(8) 3_666 . ?
N3 Cu1 O2 91.06(8) 3_666 . ?
N3 Cu1 O2 88.95(8) . . ?
O1 Cu1 O2 86.78(8) . 3_666 ?
O1 Cu1 O2 93.22(8) 3_666 3_666 ?
C10A Cu1 O2 88.94(8) 3_666 3_666 ?
N3 Cu1 O2 88.94(8) 3_666 3_666 ?
N3 Cu1 O2 91.05(8) . 3_666 ?
O2 Cu1 O2 180.0 . 3_666 ?
C2 S1 C1 103.64(15) . . ?
C8 O1 Cu1 128.84(18) . . ?
N4 O2 Cu1 112.52(16) . . ?
C8 N1 C4 124.9(3) . . ?
C8 N1 H1N 117(2) . . ?
C4 N1 H1N 117(2) . . ?
C8 N2 C9 128.2(3) . . ?
C8 N2 H2N 119(2) . . ?
C9 N2 H2N 112(2) . . ?
C9 N3 C13 115.2(2) . . ?
C9 N3 Cu1 125.16(18) . . ?
C13 N3 Cu1 119.7(2) . . ?
C11 C10 C9 117.2(3) . . ?
C11 C10 H10 121.4 . . ?
C9 C10 H10 121.4 . . ?
O3 N4 O4 121.8(2) . . ?
O3 N4 O2 120.0(2) . . ?
O4 N4 O2 118.2(2) . . ?
S1 C1 H1A 111(2) . . ?
S1 C1 H1B 112(2) . . ?
H1A C1 H1B 108(3) . . ?
S1 C1 H1C 110(2) . . ?
H1A C1 H1C 109(3) . . ?
H1B C1 H1C 107(3) . . ?
C7 C2 C3 119.5(3) . . ?
C7 C2 S1 124.8(2) . . ?
C3 C2 S1 115.6(2) . . ?
C4 C3 C2 120.0(3) . . ?
C4 C3 H3 118(2) . . ?
C2 C3 H3 122(2) . . ?
C3 C4 C5 121.0(3) . . ?
C3 C4 N1 120.8(3) . . ?
C5 C4 N1 118.1(3) . . ?
C6 C5 C4 118.5(3) . . ?
C6 C5 H5 119(2) . . ?
C4 C5 H5 123(2) . . ?
C7 C6 C5 121.4(3) . . ?
C7 C6 H6 117(2) . . ?
C5 C6 H6 122(2) . . ?
C6 C7 C2 119.6(3) . . ?
C6 C7 H7 118(2) . . ?
C2 C7 H7 122(2) . . ?
O1 C8 N1 123.1(3) . . ?
O1 C8 N2 123.7(3) . . ?
N1 C8 N2 113.2(3) . . ?
C10 C9 N3 125.9(2) . . ?
C10 C9 N2 112.9(2) . . ?
N3 C9 N2 121.2(2) . . ?
C10 C11 C12 122.0(3) . . ?
C10 C11 H11 117(2) . . ?
C12 C11 H11 121(2) . . ?
C13 C12 C11 116.6(3) . . ?
C13 C12 H12 121(2) . . ?
C11 C12 H12 123(2) . . ?
N3 C13 C12 123.1(3) . . ?
N3 C13 H13 115(2) . . ?
C12 C13 H13 122(2) . . ?

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 H1N O4 0.86(4) 1.95(4) 2.810(3) 171(3) 1_554
N2 H2N O2 0.86(4) 1.97(4) 2.817(3) 165(3) 1_554

####################################################################### 
# 
# 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_2_08SRV365
_database_code_depnum_ccdc_archive 'CCDC 1476709'
_audit_update_record             
;
2016-04-26 deposited with the CCDC.
2016-05-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97


_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H26 Br2 Cu N6 O2 S2'
_chemical_formula_weight         742.01
_chemical_melting_point          ?
_chemical_name_common            ?
_chemical_name_systematic        ?
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'
Cu Cu 0.3201 1.2651 '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'
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_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_angle_alpha                104.40(3)
_cell_angle_beta                 92.42(3)
_cell_angle_gamma                116.28(3)
_cell_formula_units_Z            1
_cell_length_a                   7.8394(16)
_cell_length_b                   8.1920(16)
_cell_length_c                   12.372(3)
_cell_measurement_reflns_used    56983
_cell_measurement_temperature    120.0(2)
_cell_measurement_theta_max      31.21
_cell_measurement_theta_min      1.97
_cell_volume                     679.3(2)
_exptl_absorpt_coefficient_mu    3.937
_exptl_absorpt_correction_T_max  0.8584
_exptl_absorpt_correction_T_min  0.5217
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_F_000             371
_exptl_crystal_colour            'clear greenish blue'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   greenish
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.814
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_exptl_special_details           ?
_diffrn_ambient_temperature      120.0(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku R-AXIS Spider IP'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_sigmaI/netI    0.0299
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            17441
_diffrn_reflns_theta_full        31.00
_diffrn_reflns_theta_max         31.00
_diffrn_reflns_theta_min         3.02
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3783
_reflns_number_total             4319
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    
;
Olex2, Durham University (compiled Sep 3 2008 19:38:20)
;
_computing_publication_material  
;
Olex2, Durham University (compiled Sep 3 2008 19:38:20)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)/Bruker'
_refine_diff_density_max         0.517
_refine_diff_density_min         -0.573
_refine_diff_density_rms         0.091
_refine_ls_R_factor_all          0.0337
_refine_ls_R_factor_gt           0.0268
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     179
_refine_ls_number_reflns         4319
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_wR_factor_gt          0.0598
_refine_ls_wR_factor_ref         0.0627
_refine_ls_weighting_details     
;
calc w=1/[σ²(Fo²)+(0.0300P)²+0.4000P] where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_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.
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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 1.0000 0.0000 0.0000 0.01242(7) Uani 1 2 d S . .
S1 S 0.67064(7) -0.30285(7) 0.44702(4) 0.01956(10) Uani 1 1 d . . .
O1 O 0.88497(16) 0.07553(17) 0.13088(10) 0.0133(2) Uani 1 1 d . . .
N1 N 0.6360(2) 0.1112(2) 0.20181(12) 0.0155(3) Uani 1 1 d . . .
H1N H 0.5290 0.1172 0.1853 0.023 Uiso 1 1 calc R . .
N2 N 0.70392(19) 0.1695(2) 0.03411(12) 0.0123(3) Uani 1 1 d . . .
H2N H 0.5901 0.1659 0.0270 0.019 Uiso 1 1 calc R . .
N3 N 0.95554(19) 0.1788(2) -0.06759(12) 0.0119(3) Uani 1 1 d . . .
C1 C 0.7678(3) -0.2456(3) 0.59397(17) 0.0251(4) Uani 1 1 d . . .
H1A H 0.6932 -0.1983 0.6420 0.030 Uiso 1 1 calc R . .
H1B H 0.9031 -0.1471 0.6105 0.030 Uiso 1 1 calc R . .
H1C H 0.7599 -0.3603 0.6093 0.030 Uiso 1 1 calc R . .
C2 C 0.7041(2) -0.0813(3) 0.43488(15) 0.0147(3) Uani 1 1 d . . .
C3 C 0.6573(2) -0.0738(2) 0.32612(14) 0.0141(3) Uani 1 1 d . . .
H3 H 0.6096 -0.1851 0.2628 0.017 Uiso 1 1 calc R . .
C4 C 0.6812(2) 0.0972(3) 0.31154(14) 0.0142(3) Uani 1 1 d . . .
C5 C 0.7454(3) 0.2605(3) 0.40364(16) 0.0209(4) Uani 1 1 d . . .
H5 H 0.7593 0.3764 0.3931 0.025 Uiso 1 1 calc R . .
C6 C 0.7889(3) 0.2508(3) 0.51115(17) 0.0250(4) Uani 1 1 d . . .
H6 H 0.8320 0.3612 0.5746 0.030 Uiso 1 1 calc R . .
C7 C 0.7702(3) 0.0828(3) 0.52717(15) 0.0198(4) Uani 1 1 d . . .
H7 H 0.8025 0.0792 0.6011 0.024 Uiso 1 1 calc R . .
C8 C 0.7501(2) 0.1157(2) 0.12255(14) 0.0114(3) Uani 1 1 d . . .
C9 C 0.8169(2) 0.2290(2) -0.04559(13) 0.0106(3) Uani 1 1 d . . .
C10 C 0.7794(2) 0.3445(2) -0.09934(14) 0.0127(3) Uani 1 1 d . . .
H10 H 0.6776 0.3747 -0.0831 0.015 Uiso 1 1 calc R . .
C11 C 0.8919(2) 0.4131(2) -0.17565(15) 0.0150(3) Uani 1 1 d . . .
H11 H 0.8683 0.4904 -0.2138 0.018 Uiso 1 1 calc R . .
C12 C 1.0424(3) 0.3674(3) -0.19656(15) 0.0164(3) Uani 1 1 d . . .
H12 H 1.1243 0.4151 -0.2478 0.020 Uiso 1 1 calc R . .
C13 C 1.0685(2) 0.2520(3) -0.14117(15) 0.0151(3) Uani 1 1 d . . .
H13 H 1.1711 0.2219 -0.1551 0.018 Uiso 1 1 calc R . .
Br1 Br 0.61611(2) -0.30883(2) -0.116232(15) 0.01596(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
Cu1 O1 1.9842(13) 2_755 ?
Cu1 O1 1.9842(13) . ?
Cu1 N3 2.0008(14) 2_755 ?
Cu1 N3 2.0008(14) . ?
S1 C2 1.7616(18) . ?
S1 C1 1.802(2) . ?
O1 C8 1.2459(19) . ?
N1 C8 1.351(2) . ?
N1 C4 1.434(2) . ?
N1 H1N 0.8800 . ?
N2 C8 1.367(2) . ?
N2 C9 1.388(2) . ?
N2 H2N 0.8800 . ?
N3 C9 1.338(2) . ?
N3 C13 1.357(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C7 1.396(3) . ?
C2 C3 1.403(2) . ?
C3 C4 1.388(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.392(3) . ?
C5 C6 1.389(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.384(3) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C9 C10 1.402(2) . ?
C10 C11 1.371(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.402(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.374(2) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O1 180.0 2_755 . ?
O1 Cu1 N3 88.88(6) 2_755 2_755 ?
O1 Cu1 N3 91.12(6) . 2_755 ?
O1 Cu1 N3 91.12(6) 2_755 . ?
O1 Cu1 N3 88.88(6) . . ?
N3 Cu1 N3 180.0 2_755 . ?
C2 S1 C1 102.87(10) . . ?
C8 O1 Cu1 123.46(11) . . ?
C8 N1 C4 123.03(13) . . ?
C8 N1 H1N 118.5 . . ?
C4 N1 H1N 118.5 . . ?
C8 N2 C9 127.14(13) . . ?
C8 N2 H2N 116.4 . . ?
C9 N2 H2N 116.4 . . ?
C9 N3 C13 117.42(14) . . ?
C9 N3 Cu1 123.41(11) . . ?
C13 N3 Cu1 119.16(11) . . ?
S1 C1 H1A 109.5 . . ?
S1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
S1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C7 C2 C3 119.34(16) . . ?
C7 C2 S1 123.50(14) . . ?
C3 C2 S1 117.15(14) . . ?
C4 C3 C2 119.62(16) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 121.06(16) . . ?
C3 C4 N1 121.38(16) . . ?
C5 C4 N1 117.53(16) . . ?
C6 C5 C4 118.84(17) . . ?
C6 C5 H5 120.6 . . ?
C4 C5 H5 120.6 . . ?
C7 C6 C5 120.99(18) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C6 C7 C2 120.12(17) . . ?
C6 C7 H7 119.9 . . ?
C2 C7 H7 119.9 . . ?
O1 C8 N1 122.51(15) . . ?
O1 C8 N2 123.87(15) . . ?
N1 C8 N2 113.62(14) . . ?
N3 C9 N2 120.59(14) . . ?
N3 C9 C10 122.67(15) . . ?
N2 C9 C10 116.74(14) . . ?
C11 C10 C9 119.02(15) . . ?
C11 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
C10 C11 C12 118.97(16) . . ?
C10 C11 H11 120.5 . . ?
C12 C11 H11 120.5 . . ?
C13 C12 C11 118.43(16) . . ?
C13 C12 H12 120.8 . . ?
C11 C12 H12 120.8 . . ?
N3 C13 C12 123.41(15) . . ?
N3 C13 H13 118.3 . . ?
C12 C13 H13 118.3 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1N Br1 0.88 2.58 3.3399(16) 145.2 2_655
N2 H2N Br1 0.88 2.53 3.2871(15) 145.0 2_655

