# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_mwll1p37ev
_database_code_depnum_ccdc_archive 'CCDC 1054559'
_audit_update_record             
;
2015-03-17 deposited with the CCDC.
2017-07-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H17 N3, 2(Cl) '
_chemical_formula_sum            'C9 H17 Cl2 N3'
_chemical_formula_weight         238.16

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   P212121

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

_cell_length_a                   9.439(5)
_cell_length_b                   10.181(5)
_cell_length_c                   13.024(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1251.6(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    4342
_cell_measurement_theta_min      2.94
_cell_measurement_theta_max      25.32

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             504
_exptl_absorpt_coefficient_mu    0.489
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.916763
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_process_details   'SADABS v2.10 BRUKER 2001'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      300(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20107
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_av_sigmaI/netI    0.0296
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.54
_diffrn_reflns_theta_max         28.52
_reflns_number_total             3157
_reflns_number_gt                2659
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger.
 H atoms were placed in calculated positions and included as riding
 contributions, except N-H hydrogens which were located in the Difference
 Fourier Map and refined freely.
 
;

_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)+(0.0432P)²+0.1060P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(7)
_refine_ls_number_reflns         3157
_refine_ls_number_parameters     143
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0381
_refine_ls_wR_factor_ref         0.0903
_refine_ls_wR_factor_gt          0.0836
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_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
Cl1 Cl 0.89490(5) 0.24528(5) 0.96202(4) 0.04626(14) Uani 1 1 d . . .
Cl2 Cl 0.92495(5) 0.73573(5) 0.85754(4) 0.04925(15) Uani 1 1 d . . .
N1 N 0.41057(18) 0.96490(16) 0.89338(13) 0.0397(4) Uani 1 1 d . . .
C1 C 0.5346(2) 0.90439(19) 0.88481(16) 0.0389(5) Uani 1 1 d . . .
N2 N 0.58340(18) 0.99612(17) 1.05454(13) 0.0390(4) Uani 1 1 d . . .
H2B H 0.520(2) 1.070(2) 1.0417(16) 0.047(6) Uiso 1 1 d . . .
H2C H 0.517(3) 0.919(3) 1.0846(19) 0.074(8) Uiso 1 1 d . . .
C2 C 0.5607(2) 0.8084(2) 0.81272(17) 0.0499(5) Uani 1 1 d . . .
H2A H 0.6517 0.7694 0.8067 0.060 Uiso 1 1 calc R . .
N3 N 0.1552(2) 1.06183(18) 0.94436(18) 0.0496(5) Uani 1 1 d . . .
H3C H 0.234(3) 1.112(3) 0.960(2) 0.073(9) Uiso 1 1 d . . .
H3B H 0.079(3) 1.126(2) 0.944(2) 0.073(8) Uiso 1 1 d . . .
C3 C 0.4513(3) 0.7709(3) 0.74990(19) 0.0622(7) Uani 1 1 d . . .
H3A H 0.4654 0.7043 0.6998 0.075 Uiso 1 1 calc R . .
C4 C 0.3210(3) 0.8301(3) 0.75970(18) 0.0549(6) Uani 1 1 d . . .
H4A H 0.2434 0.8041 0.7179 0.066 Uiso 1 1 calc R . .
C5 C 0.3062(2) 0.9276(2) 0.83145(16) 0.0415(5) Uani 1 1 d . . .
C6 C 0.6484(2) 0.9480(2) 0.95878(19) 0.0458(5) Uani 1 1 d . . .
H6A H 0.7122 0.8734 0.9742 0.055 Uiso 1 1 calc R . .
H6B H 0.7055 1.0189 0.9272 0.055 Uiso 1 1 calc R . .
C7 C 0.6876(3) 1.0325(3) 1.1345(2) 0.0560(6) Uani 1 1 d . . .
H7A H 0.6375 1.0624 1.1961 0.084 Uiso 1 1 calc R . .
H7B H 0.7484 1.1033 1.1089 0.084 Uiso 1 1 calc R . .
H7C H 0.7459 0.9559 1.1515 0.084 Uiso 1 1 calc R . .
C8 C 0.1699(2) 1.0027(2) 0.8413(2) 0.0507(6) Uani 1 1 d . . .
H8A H 0.1671 1.0729 0.7888 0.061 Uiso 1 1 calc R . .
H8B H 0.0892 0.9427 0.8285 0.061 Uiso 1 1 calc R . .
C9 C 0.1259(3) 0.9649(2) 1.0270(2) 0.0545(6) Uani 1 1 d . . .
H9A H 0.1179 1.0107 1.0929 0.082 Uiso 1 1 calc R . .
H9B H 0.2036 0.9012 1.0303 0.082 Uiso 1 1 calc R . .
H9C H 0.0370 0.9190 1.0121 0.082 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
N1 C1 1.328(3) . ?
N1 C5 1.329(3) . ?
C1 C2 1.377(3) . ?
C1 C6 1.510(3) . ?
N2 C6 1.474(3) . ?
N2 C7 1.480(3) . ?
N2 H2B 0.98(2) . ?
N2 H2C 1.08(3) . ?
C2 C3 1.372(3) . ?
C2 H2A 0.9500 . ?
N3 C8 1.478(3) . ?
N3 C9 1.486(3) . ?
N3 H3C 0.93(3) . ?
N3 H3B 0.97(3) . ?
C3 C4 1.376(4) . ?
C3 H3A 0.9500 . ?
C4 C5 1.370(3) . ?
C4 H4A 0.9500 . ?
C5 C8 1.502(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C5 118.05(18) . . ?
N1 C1 C2 123.0(2) . . ?
N1 C1 C6 115.92(19) . . ?
C2 C1 C6 121.10(19) . . ?
C6 N2 C7 113.71(17) . . ?
C6 N2 H2B 111.5(13) . . ?
C7 N2 H2B 109.6(13) . . ?
C6 N2 H2C 107.8(13) . . ?
C7 N2 H2C 108.1(14) . . ?
H2B N2 H2C 105.8(18) . . ?
C3 C2 C1 118.0(2) . . ?
C3 C2 H2A 121.0 . . ?
C1 C2 H2A 121.0 . . ?
C8 N3 C9 113.86(18) . . ?
C8 N3 H3C 110.3(17) . . ?
C9 N3 H3C 110.8(17) . . ?
C8 N3 H3B 109.8(16) . . ?
C9 N3 H3B 108.4(16) . . ?
H3C N3 H3B 103(2) . . ?
C2 C3 C4 119.7(2) . . ?
C2 C3 H3A 120.1 . . ?
C4 C3 H3A 120.1 . . ?
C5 C4 C3 118.1(2) . . ?
C5 C4 H4A 120.9 . . ?
C3 C4 H4A 120.9 . . ?
N1 C5 C4 123.1(2) . . ?
N1 C5 C8 116.0(2) . . ?
C4 C5 C8 120.9(2) . . ?
N2 C6 C1 109.98(17) . . ?
N2 C6 H6A 109.7 . . ?
C1 C6 H6A 109.7 . . ?
N2 C6 H6B 109.7 . . ?
C1 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
N2 C7 H7A 109.5 . . ?
N2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N3 C8 C5 111.46(18) . . ?
N3 C8 H8A 109.3 . . ?
C5 C8 H8A 109.3 . . ?
N3 C8 H8B 109.3 . . ?
C5 C8 H8B 109.3 . . ?
H8A C8 H8B 108.0 . . ?
N3 C9 H9A 109.5 . . ?
N3 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N3 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 2.2(3) . . . . ?
C5 N1 C1 C6 -178.47(18) . . . . ?
N1 C1 C2 C3 -2.5(3) . . . . ?
C6 C1 C2 C3 178.2(2) . . . . ?
C1 C2 C3 C4 0.7(4) . . . . ?
C2 C3 C4 C5 1.4(4) . . . . ?
C1 N1 C5 C4 0.0(3) . . . . ?
C1 N1 C5 C8 -177.66(18) . . . . ?
C3 C4 C5 N1 -1.8(4) . . . . ?
C3 C4 C5 C8 175.8(2) . . . . ?
C7 N2 C6 C1 176.00(19) . . . . ?
N1 C1 C6 N2 28.6(3) . . . . ?
C2 C1 C6 N2 -152.01(19) . . . . ?
C9 N3 C8 C5 -71.9(2) . . . . ?
N1 C5 C8 N3 -25.0(3) . . . . ?
C4 C5 C8 N3 157.2(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        28.52
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.044
﻿####################################################################### 
# 
# 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_mingbr
_database_code_depnum_ccdc_archive 'CCDC 1054555'
_audit_update_record             
;
2015-03-17 deposited with the CCDC.
2017-07-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H15 Br Cu N3, 0.33(O H2)'
_chemical_formula_sum            'C9 H15.66 Br Cu N3 O0.33'
_chemical_formula_weight         314.68

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'
Br Br -0.2901 2.4595 '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   'P2(1)/c  '

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

_cell_length_a                   9.533(12)
_cell_length_b                   15.50(2)
_cell_length_c                   8.885(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 113.710(19)
_cell_angle_gamma                90.00
_cell_volume                     1202(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    5681
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      27.60

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_min          0.20
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_max          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.739
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             627
_exptl_absorpt_coefficient_mu    5.113
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.645998
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_process_details   'SADABS v2.10 BRUKER 2001'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13398
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_av_sigmaI/netI    0.0317
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.33
_diffrn_reflns_theta_max         28.17
_reflns_number_total             2909
_reflns_number_gt                2437
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'


_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger.
 The hydrogen atoms associated with the solvent waters could
 not be located and so are omitted from the final refinement and structure
 factor calculations. They are, however, included in the reported chemical
 formula and derived values (e.g. formula weight, F(000), etc).
 
;

_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)+(0.0651P)²+1.8506P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2909
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0510
_refine_ls_R_factor_gt           0.0426
_refine_ls_wR_factor_ref         0.1309
_refine_ls_wR_factor_gt          0.1262
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_restrained_S_all      1.099
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.73842(5) 0.10265(3) 0.74896(5) 0.04558(16) Uani 1 1 d . . .
Cu1 Cu 0.56026(6) 0.16284(4) 0.47502(7) 0.04337(18) Uani 1 1 d . . .
N1 N 0.4288(4) 0.2779(2) 0.4935(4) 0.0337(7) Uani 1 1 d . . .
C1 C 0.2780(4) 0.2667(3) 0.3981(5) 0.0363(8) Uani 1 1 d . . .
N2 N 0.3378(4) 0.1101(2) 0.4091(5) 0.0406(8) Uani 1 1 d . . .
H2 H 0.320(6) 0.064(4) 0.345(7) 0.055(15) Uiso 1 1 d . . .
C2 C 0.1711(5) 0.3330(3) 0.3710(5) 0.0426(10) Uani 1 1 d . . .
H2A H 0.0659 0.3229 0.3044 0.051 Uiso 1 1 calc R . .
N3 N 0.6818(4) 0.3138(2) 0.8319(4) 0.0361(7) Uani 1 1 d . . .
H3 H 0.663(6) 0.257(4) 0.805(7) 0.054(15) Uiso 1 1 d . . .
C3 C 0.2187(6) 0.4136(3) 0.4414(6) 0.0458(10) Uani 1 1 d . . .
H3A H 0.1479 0.4596 0.4227 0.055 Uiso 1 1 calc R . .
C4 C 0.3743(6) 0.4248(3) 0.5405(5) 0.0434(10) Uani 1 1 d . . .
H4A H 0.4110 0.4791 0.5901 0.052 Uiso 1 1 calc R . .
C5 C 0.4751(5) 0.3560(3) 0.5662(5) 0.0377(8) Uani 1 1 d . . .
C6 C 0.2323(5) 0.1792(3) 0.3159(6) 0.0440(10) Uani 1 1 d . . .
H6A H 0.1274 0.1651 0.3051 0.053 Uiso 1 1 calc R . .
H6B H 0.2308 0.1822 0.2040 0.053 Uiso 1 1 calc R . .
C8 C 0.6437(5) 0.3642(3) 0.6782(5) 0.0415(9) Uani 1 1 d . . .
H8A H 0.7063 0.3431 0.6198 0.050 Uiso 1 1 calc R . .
H8B H 0.6691 0.4257 0.7059 0.050 Uiso 1 1 calc R . .
C7 C 0.3087(7) 0.0822(4) 0.5538(7) 0.0576(13) Uani 1 1 d . . .
H7A H 0.2012 0.0649 0.5179 0.086 Uiso 1 1 calc R . .
H7B H 0.3304 0.1301 0.6319 0.086 Uiso 1 1 calc R . .
H7C H 0.3752 0.0333 0.6070 0.086 Uiso 1 1 calc R . .
C9 C 0.8515(5) 0.3179(4) 0.9320(7) 0.0571(13) Uani 1 1 d . . .
H9A H 0.8784 0.2804 1.0284 0.086 Uiso 1 1 calc R . .
H9B H 0.8812 0.3774 0.9681 0.086 Uiso 1 1 calc R . .
H9C H 0.9058 0.2985 0.8650 0.086 Uiso 1 1 calc R . .
O1W O 0.9345(12) 0.1619(9) 1.0265(16) 0.070(3) Uani 0.33 1 d P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 Cu1 2.521(2) . ?
Cu1 N3 2.068(4) 4_565 ?
Cu1 N2 2.124(4) . ?
Cu1 N1 2.223(4) . ?
N1 C1 1.355(5) . ?
N1 C5 1.360(5) . ?
C1 C2 1.398(6) . ?
C1 C6 1.518(6) . ?
N2 C6 1.475(6) . ?
N2 C7 1.484(6) . ?
N2 H2 0.89(6) . ?
C2 C3 1.389(7) . ?
C2 H2A 0.9500 . ?
N3 C8 1.485(6) . ?
N3 C9 1.502(6) . ?
N3 Cu1 2.068(4) 4_566 ?
N3 H3 0.91(6) . ?
C3 C4 1.398(7) . ?
C3 H3A 0.9500 . ?
C4 C5 1.391(6) . ?
C4 H4A 0.9500 . ?
C5 C8 1.518(6) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 Cu1 N2 129.94(15) 4_565 . ?
N3 Cu1 N1 112.15(15) 4_565 . ?
N2 Cu1 N1 78.40(15) . . ?
N3 Cu1 Br1 109.39(14) 4_565 . ?
N2 Cu1 Br1 109.53(12) . . ?
N1 Cu1 Br1 113.98(10) . . ?
C1 N1 C5 118.1(3) . . ?
C1 N1 Cu1 109.8(3) . . ?
C5 N1 Cu1 131.6(3) . . ?
N1 C1 C2 122.0(4) . . ?
N1 C1 C6 116.3(4) . . ?
C2 C1 C6 121.7(4) . . ?
C6 N2 C7 112.0(4) . . ?
C6 N2 Cu1 104.8(3) . . ?
C7 N2 Cu1 112.8(3) . . ?
C6 N2 H2 109(4) . . ?
C7 N2 H2 105(4) . . ?
Cu1 N2 H2 114(3) . . ?
C3 C2 C1 120.0(4) . . ?
C3 C2 H2A 120.0 . . ?
C1 C2 H2A 120.0 . . ?
C8 N3 C9 109.3(4) . . ?
C8 N3 Cu1 118.9(3) . 4_566 ?
C9 N3 Cu1 111.4(3) . 4_566 ?
C8 N3 H3 108(3) . . ?
C9 N3 H3 104(3) . . ?
Cu1 N3 H3 104(3) 4_566 . ?
C2 C3 C4 117.8(4) . . ?
C2 C3 H3A 121.1 . . ?
C4 C3 H3A 121.1 . . ?
C5 C4 C3 119.8(4) . . ?
C5 C4 H4A 120.1 . . ?
C3 C4 H4A 120.1 . . ?
N1 C5 C4 122.2(4) . . ?
N1 C5 C8 116.2(4) . . ?
C4 C5 C8 121.6(4) . . ?
N2 C6 C1 112.3(3) . . ?
N2 C6 H6A 109.1 . . ?
C1 C6 H6A 109.1 . . ?
N2 C6 H6B 109.1 . . ?
C1 C6 H6B 109.1 . . ?
H6A C6 H6B 107.9 . . ?
N3 C8 C5 111.2(3) . . ?
N3 C8 H8A 109.4 . . ?
C5 C8 H8A 109.4 . . ?
N3 C8 H8B 109.4 . . ?
C5 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
N2 C7 H7A 109.5 . . ?
N2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N3 C9 H9A 109.5 . . ?
N3 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N3 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N3 Cu1 N1 C1 105.0(3) 4_565 . . . ?
N2 Cu1 N1 C1 -23.6(3) . . . . ?
Br1 Cu1 N1 C1 -130.0(2) . . . . ?
N3 Cu1 N1 C5 -67.1(4) 4_565 . . . ?
N2 Cu1 N1 C5 164.3(4) . . . . ?
Br1 Cu1 N1 C5 57.9(3) . . . . ?
C5 N1 C1 C2 1.1(5) . . . . ?
Cu1 N1 C1 C2 -172.2(3) . . . . ?
C5 N1 C1 C6 178.4(3) . . . . ?
Cu1 N1 C1 C6 5.1(4) . . . . ?
N3 Cu1 N2 C6 -73.4(3) 4_565 . . . ?
N1 Cu1 N2 C6 35.9(3) . . . . ?
Br1 Cu1 N2 C6 147.4(2) . . . . ?
N3 Cu1 N2 C7 164.5(3) 4_565 . . . ?
N1 Cu1 N2 C7 -86.2(3) . . . . ?
Br1 Cu1 N2 C7 25.4(3) . . . . ?
N1 C1 C2 C3 0.7(6) . . . . ?
C6 C1 C2 C3 -176.5(4) . . . . ?
C1 C2 C3 C4 -1.0(6) . . . . ?
C2 C3 C4 C5 -0.3(6) . . . . ?
C1 N1 C5 C4 -2.5(5) . . . . ?
Cu1 N1 C5 C4 169.1(3) . . . . ?
C1 N1 C5 C8 177.2(3) . . . . ?
Cu1 N1 C5 C8 -11.2(5) . . . . ?
C3 C4 C5 N1 2.2(6) . . . . ?
C3 C4 C5 C8 -177.6(4) . . . . ?
C7 N2 C6 C1 77.8(5) . . . . ?
Cu1 N2 C6 C1 -44.8(4) . . . . ?
N1 C1 C6 N2 27.1(5) . . . . ?
C2 C1 C6 N2 -155.6(4) . . . . ?
C9 N3 C8 C5 175.4(4) . . . . ?
Cu1 N3 C8 C5 -55.3(4) 4_566 . . . ?
N1 C5 C8 N3 -70.6(4) . . . . ?
C4 C5 C8 N3 109.2(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        28.17
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.844
_refine_diff_density_min         -0.606
_refine_diff_density_rms         0.109
﻿####################################################################### 
# 
# 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_MeNHPy_CuII_CH3CN_last
_database_code_depnum_ccdc_archive 'CCDC 1054556'
_audit_update_record             
;
2015-11-06 deposited with the CCDC.
2017-07-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H18 Cu F6 N4 O6 S2'
_chemical_formula_sum            'C13 H18 Cu F6 N4 O6 S2'
_chemical_formula_weight         567.97

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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                   8.1838(11)
_cell_length_b                   9.3740(14)
_cell_length_c                   14.364(2)
_cell_angle_alpha                98.975(2)
_cell_angle_beta                 94.759(2)
_cell_angle_gamma                93.248(2)
_cell_volume                     1082.0(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    6140
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      28.22

_exptl_crystal_description       plate
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.743
_exptl_crystal_F_000             574
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    1.292
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.630538
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_process_details   'SADABS v2.10 BRUKER 2001'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16356
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.205
_diffrn_reflns_theta_max         28.325
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             5148
_reflns_number_gt                4218
_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    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0481P)²+0.5787P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5148
_refine_ls_number_parameters     292
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0389
_refine_ls_wR_factor_ref         0.0992
_refine_ls_wR_factor_gt          0.0928
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.68676(3) -0.00840(3) 0.23803(2) 0.02026(9) Uani 1 1 d . . . . .
N1 N 0.8076(2) -0.1479(2) 0.31077(14) 0.0233(4) Uani 1 1 d . . . . .
H1D H 0.9226 -0.1209 0.3113 0.028 Uiso 1 1 d R U . . .
C1 C 0.7862(3) -0.3036(3) 0.2725(2) 0.0333(6) Uani 1 1 d . . . . .
H1A H 0.8485 -0.3577 0.3148 0.050 Uiso 1 1 calc R U . . .
H1B H 0.8265 -0.3206 0.2096 0.050 Uiso 1 1 calc R U . . .
H1C H 0.6694 -0.3360 0.2676 0.050 Uiso 1 1 calc R U . . .
N2 N 0.6673(2) 0.0914(2) 0.36330(13) 0.0202(4) Uani 1 1 d . . . . .
C2 C 0.7700(3) -0.1207(3) 0.41153(18) 0.0308(6) Uani 1 1 d . . . . .
H2A H 0.8696 -0.1321 0.4531 0.037 Uiso 1 1 calc R U . . .
H2B H 0.6831 -0.1931 0.4216 0.037 Uiso 1 1 calc R U . . .
N3 N 0.5577(2) 0.1575(2) 0.20232(13) 0.0220(4) Uani 1 1 d . . . . .
H3A H 0.4439 0.1250 0.2004 0.026 Uiso 1 1 d R U . . .
C3 C 0.7136(3) 0.0289(3) 0.43783(17) 0.0250(5) Uani 1 1 d . . . . .
N4 N 0.7491(3) -0.0937(2) 0.11313(14) 0.0271(4) Uani 1 1 d . . . . .
C4 C 0.7056(3) 0.1001(3) 0.52859(18) 0.0322(6) Uani 1 1 d . . . . .
H4A H 0.7372 0.0554 0.5816 0.039 Uiso 1 1 calc R U . . .
C5 C 0.6508(3) 0.2372(3) 0.54079(18) 0.0339(6) Uani 1 1 d . . . . .
H5A H 0.6444 0.2881 0.6028 0.041 Uiso 1 1 calc R U . . .
C6 C 0.6047(3) 0.3014(3) 0.46256(18) 0.0294(5) Uani 1 1 d . . . . .
H6A H 0.5664 0.3960 0.4705 0.035 Uiso 1 1 calc R U . . .
C7 C 0.6156(3) 0.2253(3) 0.37314(16) 0.0216(5) Uani 1 1 d . . . . .
C8 C 0.5854(3) 0.2808(2) 0.28106(17) 0.0230(5) Uani 1 1 d . . . . .
H8A H 0.4880 0.3388 0.2827 0.028 Uiso 1 1 calc R U . . .
H8B H 0.6815 0.3440 0.2713 0.028 Uiso 1 1 calc R U . . .
C9 C 0.5775(3) 0.2050(3) 0.11053(18) 0.0324(6) Uani 1 1 d . . . . .
H9A H 0.5061 0.2837 0.1030 0.049 Uiso 1 1 calc R U . . .
H9B H 0.5473 0.1235 0.0592 0.049 Uiso 1 1 calc R U . . .
H9C H 0.6922 0.2394 0.1084 0.049 Uiso 1 1 calc R U . . .
C10 C 0.8138(3) -0.1354(3) 0.04914(17) 0.0250(5) Uani 1 1 d . . . . .
C11 C 0.8992(4) -0.1884(3) -0.03287(19) 0.0371(6) Uani 1 1 d . . . . .
H11A H 0.8641 -0.1387 -0.0855 0.056 Uiso 1 1 calc R U . . .
H11B H 0.8729 -0.2929 -0.0513 0.056 Uiso 1 1 calc R U . . .
H11C H 1.0180 -0.1694 -0.0170 0.056 Uiso 1 1 calc R U . . .
S1 S 0.28763(7) -0.18347(6) 0.17568(4) 0.02463(14) Uani 1 1 d . . . . .
O1 O 0.4332(2) -0.1526(2) 0.24203(12) 0.0307(4) Uani 1 1 d . . . . .
F1 F 0.1958(3) -0.4130(2) 0.04935(17) 0.0776(7) Uani 1 1 d . . . . .
O2 O 0.2838(3) -0.0985(2) 0.10024(13) 0.0384(5) Uani 1 1 d . . . . .
F2 F 0.4556(3) -0.3677(2) 0.07277(14) 0.0579(5) Uani 1 1 d . . . . .
O3 O 0.1377(2) -0.2016(2) 0.21811(17) 0.0457(5) Uani 1 1 d . . . . .
F3 F 0.3278(3) -0.4590(2) 0.17552(15) 0.0590(5) Uani 1 1 d . . . . .
C12 C 0.3171(4) -0.3649(3) 0.1155(2) 0.0390(7) Uani 1 1 d . . . . .
S2 S 1.07785(7) 0.18903(6) 0.30098(4) 0.02266(13) Uani 1 1 d . . . . .
F4 F 1.2162(2) 0.3889(2) 0.43609(15) 0.0578(5) Uani 1 1 d . . . . .
F5 F 0.9561(2) 0.3988(2) 0.40963(15) 0.0574(6) Uani 1 1 d . . . . .
F6 F 1.1130(3) 0.4701(2) 0.31435(18) 0.0727(7) Uani 1 1 d . . . . .
O4 O 0.9358(2) 0.1853(2) 0.23396(12) 0.0323(4) Uani 1 1 d . . . . .
O5 O 1.0564(2) 0.0998(2) 0.37232(14) 0.0363(4) Uani 1 1 d . . . . .
O6 O 1.2321(2) 0.1834(2) 0.26056(15) 0.0415(5) Uani 1 1 d . . . . .
C13 C 1.0911(3) 0.3709(3) 0.3686(2) 0.0350(6) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N2 1.9178(19) . ?
Cu1 N4 1.967(2) . ?
Cu1 N3 2.0351(19) . ?
Cu1 N1 2.0446(19) . ?
Cu1 O1 2.4213(18) . ?
N1 C1 1.472(3) . ?
N1 C2 1.491(3) . ?
N1 H1D 0.9600 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
N2 C3 1.337(3) . ?
N2 C7 1.337(3) . ?
C2 C3 1.504(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
N3 C9 1.474(3) . ?
N3 C8 1.479(3) . ?
N3 H3A 0.9600 . ?
C3 C4 1.377(3) . ?
N4 C10 1.127(3) . ?
C4 C5 1.375(4) . ?
C4 H4A 0.9500 . ?
C5 C6 1.391(4) . ?
C5 H5A 0.9500 . ?
C6 C7 1.381(3) . ?
C6 H6A 0.9500 . ?
C7 C8 1.502(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.455(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
S1 O3 1.428(2) . ?
S1 O2 1.4407(19) . ?
S1 O1 1.4481(18) . ?
S1 C12 1.823(3) . ?
F1 C12 1.323(3) . ?
F2 C12 1.333(4) . ?
F3 C12 1.328(3) . ?
S2 O6 1.4325(19) . ?
S2 O5 1.4358(19) . ?
S2 O4 1.4418(17) . ?
S2 C13 1.819(3) . ?
F4 C13 1.335(3) . ?
F5 C13 1.315(3) . ?
F6 C13 1.316(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
N2 Cu1 N4 169.22(8) . . ?
N2 Cu1 N3 81.75(8) . . ?
N4 Cu1 N3 100.34(8) . . ?
N2 Cu1 N1 82.46(8) . . ?
N4 Cu1 N1 95.34(8) . . ?
N3 Cu1 N1 164.18(8) . . ?
N2 Cu1 O1 90.63(7) . . ?
N4 Cu1 O1 99.89(8) . . ?
N3 Cu1 O1 90.49(7) . . ?
N1 Cu1 O1 88.79(7) . . ?
C1 N1 C2 110.8(2) . . ?
C1 N1 Cu1 118.06(16) . . ?
C2 N1 Cu1 109.15(14) . . ?
C1 N1 H1D 106.0 . . ?
C2 N1 H1D 106.0 . . ?
Cu1 N1 H1D 106.0 . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 N2 C7 122.1(2) . . ?
C3 N2 Cu1 119.38(16) . . ?
C7 N2 Cu1 118.46(16) . . ?
N1 C2 C3 111.2(2) . . ?
N1 C2 H2A 109.4 . . ?
C3 C2 H2A 109.4 . . ?
N1 C2 H2B 109.4 . . ?
C3 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
C9 N3 C8 111.17(19) . . ?
C9 N3 Cu1 119.06(15) . . ?
C8 N3 Cu1 108.48(14) . . ?
C9 N3 H3A 105.8 . . ?
C8 N3 H3A 105.6 . . ?
Cu1 N3 H3A 105.7 . . ?
N2 C3 C4 120.6(2) . . ?
N2 C3 C2 113.7(2) . . ?
C4 C3 C2 125.7(2) . . ?
C10 N4 Cu1 167.1(2) . . ?
C5 C4 C3 118.6(2) . . ?
C5 C4 H4A 120.7 . . ?
C3 C4 H4A 120.7 . . ?
C4 C5 C6 120.2(2) . . ?
C4 C5 H5A 119.9 . . ?
C6 C5 H5A 119.9 . . ?
C7 C6 C5 118.8(2) . . ?
C7 C6 H6A 120.6 . . ?
C5 C6 H6A 120.6 . . ?
N2 C7 C6 119.8(2) . . ?
N2 C7 C8 113.6(2) . . ?
C6 C7 C8 126.5(2) . . ?
N3 C8 C7 109.64(18) . . ?
N3 C8 H8A 109.7 . . ?
C7 C8 H8A 109.7 . . ?
N3 C8 H8B 109.7 . . ?
C7 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
N3 C9 H9A 109.5 . . ?
N3 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N3 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N4 C10 C11 179.3(3) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O3 S1 O2 116.44(13) . . ?
O3 S1 O1 114.69(12) . . ?
O2 S1 O1 114.11(12) . . ?
O3 S1 C12 103.56(14) . . ?
O2 S1 C12 103.20(12) . . ?
O1 S1 C12 102.27(13) . . ?
S1 O1 Cu1 131.57(11) . . ?
F1 C12 F3 108.2(3) . . ?
F1 C12 F2 106.9(3) . . ?
F3 C12 F2 106.7(2) . . ?
F1 C12 S1 111.7(2) . . ?
F3 C12 S1 111.7(2) . . ?
F2 C12 S1 111.3(2) . . ?
O6 S2 O5 115.83(13) . . ?
O6 S2 O4 115.03(12) . . ?
O5 S2 O4 114.06(11) . . ?
O6 S2 C13 102.71(12) . . ?
O5 S2 C13 102.60(13) . . ?
O4 S2 C13 104.19(12) . . ?
F5 C13 F6 106.6(2) . . ?
F5 C13 F4 107.8(2) . . ?
F6 C13 F4 107.8(2) . . ?
F5 C13 S2 111.89(19) . . ?
F6 C13 S2 111.7(2) . . ?
F4 C13 S2 110.87(19) . . ?

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
C1 N1 C2 C3 -153.3(2) . . . . ?
Cu1 N1 C2 C3 -21.7(3) . . . . ?
C7 N2 C3 C4 1.6(4) . . . . ?
Cu1 N2 C3 C4 178.01(19) . . . . ?
C7 N2 C3 C2 -179.1(2) . . . . ?
Cu1 N2 C3 C2 -2.7(3) . . . . ?
N1 C2 C3 N2 16.6(3) . . . . ?
N1 C2 C3 C4 -164.1(2) . . . . ?
N2 C3 C4 C5 -0.7(4) . . . . ?
C2 C3 C4 C5 -179.9(3) . . . . ?
C3 C4 C5 C6 0.0(4) . . . . ?
C4 C5 C6 C7 -0.2(4) . . . . ?
C3 N2 C7 C6 -1.8(3) . . . . ?
Cu1 N2 C7 C6 -178.20(18) . . . . ?
C3 N2 C7 C8 174.2(2) . . . . ?
Cu1 N2 C7 C8 -2.2(3) . . . . ?
C5 C6 C7 N2 1.1(4) . . . . ?
C5 C6 C7 C8 -174.4(2) . . . . ?
C9 N3 C8 C7 -162.82(19) . . . . ?
Cu1 N3 C8 C7 -30.1(2) . . . . ?
N2 C7 C8 N3 22.0(3) . . . . ?
C6 C7 C8 N3 -162.3(2) . . . . ?
O3 S1 O1 Cu1 -147.42(14) . . . . ?
O2 S1 O1 Cu1 -9.45(19) . . . . ?
C12 S1 O1 Cu1 101.23(16) . . . . ?
O3 S1 C12 F1 61.6(3) . . . . ?
O2 S1 C12 F1 -60.2(3) . . . . ?
O1 S1 C12 F1 -178.9(2) . . . . ?
O3 S1 C12 F3 -59.8(2) . . . . ?
O2 S1 C12 F3 178.4(2) . . . . ?
O1 S1 C12 F3 59.7(2) . . . . ?
O3 S1 C12 F2 -178.9(2) . . . . ?
O2 S1 C12 F2 59.3(2) . . . . ?
O1 S1 C12 F2 -59.4(2) . . . . ?
O6 S2 C13 F5 178.2(2) . . . . ?
O5 S2 C13 F5 -61.3(2) . . . . ?
O4 S2 C13 F5 57.9(2) . . . . ?
O6 S2 C13 F6 58.8(2) . . . . ?
O5 S2 C13 F6 179.4(2) . . . . ?
O4 S2 C13 F6 -61.5(2) . . . . ?
O6 S2 C13 F4 -61.5(2) . . . . ?
O5 S2 C13 F4 59.1(2) . . . . ?
O4 S2 C13 F4 178.2(2) . . . . ?

_refine_diff_density_max         0.649
_refine_diff_density_min         -0.414
_refine_diff_density_rms         0.080

_shelxl_version_number           2013-3

