# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1484103'
_audit_update_record             
;
2016-06-08 deposited with the CCDC.
2016-07-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H14 N6, 2(Cl)'
_chemical_formula_sum            'C5 H14 Cl2 N6'
_chemical_formula_weight         229.12

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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                   7.4185(10)
_cell_length_b                   7.9458(10)
_cell_length_c                   9.3820(12)
_cell_angle_alpha                74.7992(14)
_cell_angle_beta                 79.8889(14)
_cell_angle_gamma                89.0669(15)
_cell_volume                     525.14(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2338
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      28.06

_exptl_crystal_description       lamina
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_F_000             240
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.586
_shelx_estimated_absorpt_T_min   0.844
_shelx_estimated_absorpt_T_max   0.971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6860
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4787
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_av_R_equivalents  0.0153
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.286
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2051
_reflns_number_gt                1746
_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       'APEX2 (Bruker, 2010)'
_computing_cell_refinement       'SAINT (Bruker, 2010)'
_computing_data_reduction        'SAINT (Bruker, 2010)'
_computing_structure_solution    'SIR2014 (Burla et al., 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  
;
SHELXL-2014/7 (Sheldrick, 2015),
PLATON (Spek, 2009)
;

_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)+(0.0431P)²+0.0479P] 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         2051
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0262
_refine_ls_wR_factor_ref         0.0718
_refine_ls_wR_factor_gt          0.0678
_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_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
Cl1 Cl 0.12171(5) 0.22539(6) 0.53664(5) 0.03854(13) Uani 1 1 d . . . . .
Cl2 Cl 0.42809(6) 0.46616(5) 0.76746(5) 0.04144(14) Uani 1 1 d . . . . .
N1 N 0.01284(17) 0.25257(17) 0.05251(14) 0.0313(3) Uani 1 1 d . . . . .
N2 N -0.14831(19) 0.1800(2) 0.13597(17) 0.0445(4) Uani 1 1 d . . . . .
N3 N -0.23330(19) 0.1255(2) 0.04684(19) 0.0482(4) Uani 1 1 d . . . . .
N4 N -0.13129(18) 0.16018(19) -0.09378(16) 0.0395(3) Uani 1 1 d . . . . .
C5 C 0.0195(2) 0.2374(2) -0.08599(19) 0.0344(4) Uani 1 1 d . . . . .
H5 H 0.113(2) 0.275(2) -0.1580(19) 0.032(4) Uiso 1 1 d . . . . .
C6 C 0.1495(3) 0.3239(2) 0.1180(2) 0.0376(4) Uani 1 1 d . . . . .
H6A H 0.198(2) 0.429(2) 0.048(2) 0.039(5) Uiso 1 1 d . . . . .
H6B H 0.086(2) 0.348(2) 0.203(2) 0.035(5) Uiso 1 1 d . . . . .
C7 C 0.3049(2) 0.2032(2) 0.14960(19) 0.0339(4) Uani 1 1 d . . . . .
H7A H 0.353(2) 0.160(2) 0.065(2) 0.034(4) Uiso 1 1 d . . . . .
H7B H 0.399(2) 0.268(2) 0.178(2) 0.047(5) Uiso 1 1 d . . . . .
N8 N 0.24766(17) 0.04686(17) 0.27830(15) 0.0287(3) Uani 1 1 d . . . . .
H8A H 0.166(2) -0.017(2) 0.2563(19) 0.038(5) Uiso 1 1 d . . . . .
H8B H 0.199(2) 0.085(3) 0.359(2) 0.048(5) Uiso 1 1 d . . . . .
C9 C 0.4082(2) -0.0609(2) 0.31611(19) 0.0332(4) Uani 1 1 d . . . . .
H9A H 0.450(2) -0.111(2) 0.241(2) 0.040(5) Uiso 1 1 d . . . . .
H9B H 0.501(2) 0.020(2) 0.315(2) 0.040(5) Uiso 1 1 d . . . . .
C10 C 0.3721(2) -0.1918(2) 0.46653(19) 0.0340(4) Uani 1 1 d . . . . .
H10A H 0.489(2) -0.225(2) 0.4932(18) 0.035(4) Uiso 1 1 d . . . . .
H10B H 0.300(2) -0.146(2) 0.537(2) 0.038(5) Uiso 1 1 d . . . . .
N11 N 0.2785(2) -0.35507(19) 0.46711(19) 0.0383(3) Uani 1 1 d . . . . .
H11A H 0.342(3) -0.397(3) 0.393(2) 0.052(6) Uiso 1 1 d . . . . .
H11B H 0.157(3) -0.342(3) 0.461(2) 0.052(5) Uiso 1 1 d . . . . .
H11C H 0.286(3) -0.432(3) 0.551(2) 0.051(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
N1 C5 1.329(2) . ?
N1 N2 1.3534(18) . ?
N1 C6 1.465(2) . ?
N2 N3 1.292(2) . ?
N3 N4 1.362(2) . ?
N4 C5 1.307(2) . ?
C5 H5 0.872(17) . ?
C6 C7 1.507(2) . ?
C6 H6A 0.946(19) . ?
C6 H6B 0.919(18) . ?
C7 N8 1.494(2) . ?
C7 H7A 0.951(17) . ?
C7 H7B 0.987(19) . ?
N8 C9 1.495(2) . ?
N8 H8A 0.882(18) . ?
N8 H8B 0.90(2) . ?
C9 C10 1.500(2) . ?
C9 H9A 0.904(19) . ?
C9 H9B 0.944(18) . ?
C10 N11 1.480(2) . ?
C10 H10A 0.959(17) . ?
C10 H10B 0.928(19) . ?
N11 H11A 0.90(2) . ?
N11 H11B 0.92(2) . ?
N11 H11C 0.87(2) . ?

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
C5 N1 N2 107.94(13) . . ?
C5 N1 C6 130.23(14) . . ?
N2 N1 C6 121.77(14) . . ?
N3 N2 N1 106.25(13) . . ?
N2 N3 N4 110.75(13) . . ?
C5 N4 N3 105.48(14) . . ?
N4 C5 N1 109.57(15) . . ?
N4 C5 H5 127.4(11) . . ?
N1 C5 H5 123.0(11) . . ?
N1 C6 C7 113.19(14) . . ?
N1 C6 H6A 107.3(10) . . ?
C7 C6 H6A 108.3(10) . . ?
N1 C6 H6B 105.9(10) . . ?
C7 C6 H6B 112.3(10) . . ?
H6A C6 H6B 109.7(15) . . ?
N8 C7 C6 112.56(14) . . ?
N8 C7 H7A 106.5(10) . . ?
C6 C7 H7A 111.5(10) . . ?
N8 C7 H7B 106.8(11) . . ?
C6 C7 H7B 107.7(11) . . ?
H7A C7 H7B 111.8(14) . . ?
C7 N8 C9 111.19(12) . . ?
C7 N8 H8A 109.9(11) . . ?
C9 N8 H8A 109.7(11) . . ?
C7 N8 H8B 107.9(12) . . ?
C9 N8 H8B 107.8(11) . . ?
H8A N8 H8B 110.3(16) . . ?
N8 C9 C10 114.24(13) . . ?
N8 C9 H9A 109.2(11) . . ?
C10 C9 H9A 112.1(11) . . ?
N8 C9 H9B 105.3(10) . . ?
C10 C9 H9B 109.4(11) . . ?
H9A C9 H9B 106.0(16) . . ?
N11 C10 C9 114.08(14) . . ?
N11 C10 H10A 105.9(10) . . ?
C9 C10 H10A 106.9(10) . . ?
N11 C10 H10B 107.0(11) . . ?
C9 C10 H10B 111.0(11) . . ?
H10A C10 H10B 111.9(15) . . ?
C10 N11 H11A 108.2(13) . . ?
C10 N11 H11B 113.3(13) . . ?
H11A N11 H11B 112.8(18) . . ?
C10 N11 H11C 108.0(13) . . ?
H11A N11 H11C 106.5(19) . . ?
H11B N11 H11C 107.6(18) . . ?

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 N2 N3 -0.53(17) . . . . ?
C6 N1 N2 N3 -177.89(14) . . . . ?
N1 N2 N3 N4 0.17(18) . . . . ?
N2 N3 N4 C5 0.25(19) . . . . ?
N3 N4 C5 N1 -0.58(18) . . . . ?
N2 N1 C5 N4 0.71(18) . . . . ?
C6 N1 C5 N4 177.76(15) . . . . ?
C5 N1 C6 C7 -75.5(2) . . . . ?
N2 N1 C6 C7 101.17(18) . . . . ?
N1 C6 C7 N8 -71.19(19) . . . . ?
C6 C7 N8 C9 -174.49(14) . . . . ?
C7 N8 C9 C10 164.72(14) . . . . ?
N8 C9 C10 N11 81.73(19) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N8 H8A N4 0.882(18) 2.177(19) 2.918(2) 141.2(15) 2
N8 H8B Cl1 0.90(2) 2.23(2) 3.1184(15) 168.0(17) .
N11 H11A Cl2 0.90(2) 2.23(2) 3.1041(17) 161.9(17) 2_656
N11 H11B Cl1 0.92(2) 2.25(2) 3.1295(16) 160.6(17) 2_556
N11 H11C Cl2 0.87(2) 2.40(2) 3.1840(18) 150.2(17) 1_545
C5 H5 Cl2 0.872(17) 2.694(17) 3.4334(17) 143.3(14) 1_554
C7 H7B Cl2 0.987(19) 2.69(2) 3.6351(18) 159.8(14) 2_666

_refine_diff_density_max         0.193
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.037

####################################################################### 
# 
# 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_V_100
_database_code_depnum_ccdc_archive 'CCDC 1484104'
_audit_update_record             
;
2016-06-08 deposited with the CCDC.
2016-07-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H22 Cl2 Cu2 N12'
_chemical_formula_sum            'C10 H22 Cl2 Cu2 N12'
_chemical_formula_weight         508.37

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.62760(10)
_cell_length_b                   10.01430(10)
_cell_length_c                   12.5130(2)
_cell_angle_alpha                90
_cell_angle_beta                 103.0549(6)
_cell_angle_gamma                90
_cell_volume                     931.10(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9951
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      33.20

_exptl_crystal_description       prism
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.813
_exptl_crystal_F_000             516
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    2.595
_shelx_estimated_absorpt_T_min   0.541
_shelx_estimated_absorpt_T_max   0.697
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6457
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13312
_diffrn_reflns_av_unetI/netI     0.0151
_diffrn_reflns_av_R_equivalents  0.0147
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.632
_diffrn_reflns_theta_max         33.203
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3573
_reflns_number_gt                3355
_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       'APEX2 (Bruker, 2010)'
_computing_cell_refinement       'SAINT (Bruker, 2010)'
_computing_data_reduction        'SAINT (Bruker, 2010)'
_computing_structure_solution    'SIR2014 (Burla et al., 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  
;
SHELXL-2014/7 (Sheldrick, 2015),
PLATON (Spek, 2009)
;
_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)+(0.0271P)²+0.5393P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3573
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0216
_refine_ls_R_factor_gt           0.0199
_refine_ls_wR_factor_ref         0.0527
_refine_ls_wR_factor_gt          0.0521
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_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 0.51436(2) 0.18373(2) 0.07085(2) 0.00983(4) Uani 1 1 d . . . . .
Cl1 Cl 0.63917(3) 0.35035(2) -0.04854(2) 0.01365(5) Uani 1 1 d . . . . .
N1 N 0.15268(12) 0.13998(10) -0.07000(8) 0.01429(16) Uani 1 1 d . . . . .
N2 N 0.04110(13) 0.05220(10) -0.13479(9) 0.01865(19) Uani 1 1 d . . . . .
N3 N 0.13296(12) -0.05520(10) -0.13574(9) 0.01637(17) Uani 1 1 d . . . . .
N4 N 0.30308(12) -0.03765(9) -0.07217(7) 0.01167(15) Uani 1 1 d . . . . .
C5 C 0.31671(13) 0.08615(10) -0.02996(8) 0.01109(16) Uani 1 1 d . . . . .
C6 C 0.08787(15) 0.27349(12) -0.05262(10) 0.0189(2) Uani 1 1 d . . . . .
H6A H -0.0451 0.2753 -0.0757 0.023 Uiso 1 1 calc R U . . .
H6B H 0.1361 0.3384 -0.0983 0.023 Uiso 1 1 calc R U . . .
C7 C 0.14568(15) 0.31362(12) 0.06703(11) 0.0179(2) Uani 1 1 d . . . . .
H7A H 0.0844 0.3976 0.0790 0.022 Uiso 1 1 calc R U . . .
H7B H 0.1092 0.2435 0.1134 0.022 Uiso 1 1 calc R U . . .
N8 N 0.34137(13) 0.33276(9) 0.09963(8) 0.01287(15) Uani 1 1 d . . . . .
H8 H 0.371(2) 0.3999(17) 0.0579(13) 0.015 Uiso 1 1 d . U . . .
C9 C 0.39887(16) 0.37269(12) 0.21552(9) 0.01620(19) Uani 1 1 d . . . . .
H9A H 0.3657 0.3031 0.2636 0.019 Uiso 1 1 calc R U . . .
H9B H 0.3401 0.4575 0.2283 0.019 Uiso 1 1 calc R U . . .
C10 C 0.60042(16) 0.39003(11) 0.23993(9) 0.01693(19) Uani 1 1 d . . . . .
H10A H 0.6334 0.4644 0.1962 0.020 Uiso 1 1 calc R U . . .
H10B H 0.6476 0.4098 0.3187 0.020 Uiso 1 1 calc R U . . .
N11 N 0.67480(13) 0.26281(10) 0.21016(8) 0.01414(16) Uani 1 1 d . . . . .
H11A H 0.679(2) 0.2072(17) 0.2665(14) 0.017 Uiso 1 1 d . U . . .
H11B H 0.786(2) 0.2720(17) 0.2002(14) 0.017 Uiso 1 1 d . U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 C5 1.9900(10) . ?
Cu1 N4 2.0172(9) 3_655 ?
Cu1 N11 2.0493(9) . ?
Cu1 N8 2.0767(9) . ?
Cu1 Cl1 2.5622(3) . ?
N1 C5 1.3505(13) . ?
N1 N2 1.3575(13) . ?
N1 C6 1.4587(15) . ?
N2 N3 1.2851(14) . ?
N3 N4 1.3715(12) . ?
N4 C5 1.3424(13) . ?
N4 Cu1 2.0172(9) 3_655 ?
C6 C7 1.5164(17) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 N8 1.4684(15) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
N8 C9 1.4723(15) . ?
N8 H8 0.911(17) . ?
C9 C10 1.5082(16) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 N11 1.4762(15) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
N11 H11A 0.893(17) . ?
N11 H11B 0.890(17) . ?

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
C5 Cu1 N4 94.12(4) . 3_655 ?
C5 Cu1 N11 161.87(4) . . ?
N4 Cu1 N11 89.70(4) 3_655 . ?
C5 Cu1 N8 92.45(4) . . ?
N4 Cu1 N8 169.81(4) 3_655 . ?
N11 Cu1 N8 81.69(4) . . ?
C5 Cu1 Cl1 106.15(3) . . ?
N4 Cu1 Cl1 97.49(3) 3_655 . ?
N11 Cu1 Cl1 90.87(3) . . ?
N8 Cu1 Cl1 88.13(3) . . ?
C5 N1 N2 111.50(9) . . ?
C5 N1 C6 128.85(9) . . ?
N2 N1 C6 119.65(9) . . ?
N3 N2 N1 106.14(9) . . ?
N2 N3 N4 109.50(9) . . ?
C5 N4 N3 109.00(8) . . ?
C5 N4 Cu1 132.42(7) . 3_655 ?
N3 N4 Cu1 118.21(7) . 3_655 ?
N4 C5 N1 103.87(9) . . ?
N4 C5 Cu1 133.09(7) . . ?
N1 C5 Cu1 123.02(8) . . ?
N1 C6 C7 110.94(10) . . ?
N1 C6 H6A 109.5 . . ?
C7 C6 H6A 109.5 . . ?
N1 C6 H6B 109.5 . . ?
C7 C6 H6B 109.5 . . ?
H6A C6 H6B 108.0 . . ?
N8 C7 C6 111.07(9) . . ?
N8 C7 H7A 109.4 . . ?
C6 C7 H7A 109.4 . . ?
N8 C7 H7B 109.4 . . ?
C6 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
C7 N8 C9 111.53(9) . . ?
C7 N8 Cu1 120.26(7) . . ?
C9 N8 Cu1 107.84(7) . . ?
C7 N8 H8 107.9(10) . . ?
C9 N8 H8 107.8(10) . . ?
Cu1 N8 H8 100.4(10) . . ?
N8 C9 C10 107.10(9) . . ?
N8 C9 H9A 110.3 . . ?
C10 C9 H9A 110.3 . . ?
N8 C9 H9B 110.3 . . ?
C10 C9 H9B 110.3 . . ?
H9A C9 H9B 108.5 . . ?
N11 C10 C9 106.37(9) . . ?
N11 C10 H10A 110.5 . . ?
C9 C10 H10A 110.5 . . ?
N11 C10 H10B 110.5 . . ?
C9 C10 H10B 110.5 . . ?
H10A C10 H10B 108.6 . . ?
C10 N11 Cu1 111.01(7) . . ?
C10 N11 H11A 106.6(11) . . ?
Cu1 N11 H11A 109.8(11) . . ?
C10 N11 H11B 112.3(11) . . ?
Cu1 N11 H11B 109.0(11) . . ?
H11A N11 H11B 108.1(15) . . ?

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 N2 N3 -0.03(13) . . . . ?
C6 N1 N2 N3 179.63(10) . . . . ?
N1 N2 N3 N4 -0.03(13) . . . . ?
N2 N3 N4 C5 0.08(13) . . . . ?
N2 N3 N4 Cu1 -173.84(8) . . . 3_655 ?
N3 N4 C5 N1 -0.09(11) . . . . ?
Cu1 N4 C5 N1 172.64(8) 3_655 . . . ?
N3 N4 C5 Cu1 178.45(8) . . . . ?
Cu1 N4 C5 Cu1 -8.82(16) 3_655 . . . ?
N2 N1 C5 N4 0.08(12) . . . . ?
C6 N1 C5 N4 -179.54(11) . . . . ?
N2 N1 C5 Cu1 -178.65(8) . . . . ?
C6 N1 C5 Cu1 1.73(16) . . . . ?
C5 N1 C6 C7 -44.01(16) . . . . ?
N2 N1 C6 C7 136.40(11) . . . . ?
N1 C6 C7 N8 68.11(12) . . . . ?
C6 C7 N8 C9 179.60(9) . . . . ?
C6 C7 N8 Cu1 -52.70(12) . . . . ?
C7 N8 C9 C10 -179.78(9) . . . . ?
Cu1 N8 C9 C10 46.11(10) . . . . ?
N8 C9 C10 N11 -55.47(11) . . . . ?
C9 C10 N11 Cu1 38.26(10) . . . . ?

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
C6 H6A Cl1 0.99 2.62 3.5196(12) 152. 1_455
N11 H11B N3 0.890(17) 2.444(17) 2.8208(14) 105.9(13) 3_655
N8 H8 Cl1 0.911(17) 2.504(17) 3.2472(10) 139.0(13) 3_665
N8 H8 Cl1 0.911(17) 2.725(16) 3.2451(10) 117.2(12) .
N11 H11A Cl1 0.893(17) 2.469(18) 3.2933(10) 153.6(15) 4_566

_refine_diff_density_max         0.977
_refine_diff_density_min         -0.492
_refine_diff_density_rms         0.067

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

data_V_296
_database_code_depnum_ccdc_archive 'CCDC 1484105'
_audit_update_record             
;
2016-06-08 deposited with the CCDC.
2016-07-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H22 Cl2 Cu2 N12'
_chemical_formula_sum            'C10 H22 Cl2 Cu2 N12'
_chemical_formula_weight         508.37

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.6575(2)
_cell_length_b                   10.0729(3)
_cell_length_c                   12.6180(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.1342(14)
_cell_angle_gamma                90
_cell_volume                     947.81(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4435
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      30.26

_exptl_crystal_description       prism
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.781
_exptl_crystal_F_000             516
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    2.549
_shelx_estimated_absorpt_T_min   0.505
_shelx_estimated_absorpt_T_max   0.767
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6064
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9864
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.615
_diffrn_reflns_theta_max         30.650
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2916
_reflns_number_gt                2389
_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       'APEX2 (Bruker, 2010)'
_computing_cell_refinement       'SAINT (Bruker, 2010)'
_computing_data_reduction        'SAINT (Bruker, 2010)'
_computing_structure_solution    'SIR2014 (Burla et al., 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  
;
SHELXL-2014/7 (Sheldrick, 2015),
PLATON (Spek, 2009)
;
_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)+(0.0493P)²+0.3381P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2916
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0313
_refine_ls_wR_factor_ref         0.0874
_refine_ls_wR_factor_gt          0.0811
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_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 0.51731(3) 0.18422(2) 0.57194(2) 0.03052(9) Uani 1 1 d . . . . .
Cl1 Cl 0.64222(8) 0.34983(5) 0.45149(4) 0.03978(13) Uani 1 1 d . . . . .
N1 N 0.1579(3) 0.1411(2) 0.43294(17) 0.0440(4) Uani 1 1 d . . . . .
N2 N 0.0458(3) 0.0552(2) 0.3678(2) 0.0575(6) Uani 1 1 d . . . . .
N3 N 0.1360(3) -0.0510(2) 0.36539(19) 0.0506(5) Uani 1 1 d . . . . .
N4 N 0.3046(2) -0.03567(18) 0.42851(14) 0.0365(4) Uani 1 1 d . . . . .
C5 C 0.3196(3) 0.0872(2) 0.47215(16) 0.0351(4) Uani 1 1 d . . . . .
C6 C 0.0945(4) 0.2720(3) 0.4518(3) 0.0556(7) Uani 1 1 d . . . . .
H6A H -0.0353 0.2737 0.4299 0.067 Uiso 1 1 calc R U . . .
H6B H 0.1405 0.3358 0.4073 0.067 Uiso 1 1 calc R U . . .
C7 C 0.1527(3) 0.3120(3) 0.5697(2) 0.0500(6) Uani 1 1 d . . . . .
H7A H 0.0919 0.3933 0.5815 0.060 Uiso 1 1 calc R U . . .
H7B H 0.1183 0.2433 0.6149 0.060 Uiso 1 1 calc R U . . .
N8 N 0.3464(3) 0.33235(18) 0.60172(15) 0.0352(4) Uani 1 1 d . . . . .
H8 H 0.369(3) 0.404(3) 0.560(2) 0.042 Uiso 1 1 d . U . . .
C9 C 0.4058(4) 0.3724(2) 0.71552(18) 0.0452(5) Uani 1 1 d . . . . .
H9A H 0.3734 0.3053 0.7628 0.054 Uiso 1 1 calc R U . . .
H9B H 0.3493 0.4555 0.7278 0.054 Uiso 1 1 calc R U . . .
C10 C 0.6059(4) 0.3888(2) 0.73914(19) 0.0469(5) Uani 1 1 d . . . . .
H10A H 0.6382 0.4611 0.6965 0.056 Uiso 1 1 calc R U . . .
H10B H 0.6528 0.4079 0.8157 0.056 Uiso 1 1 calc R U . . .
N11 N 0.6790(3) 0.2623(2) 0.70944(16) 0.0407(4) Uani 1 1 d . . . . .
H11A H 0.686(4) 0.208(3) 0.766(3) 0.049 Uiso 1 1 d . U . . .
H11B H 0.775(4) 0.274(3) 0.698(2) 0.049 Uiso 1 1 d . U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 C5 1.991(2) . ?
Cu1 N4 2.0252(18) 3_656 ?
Cu1 N11 2.046(2) . ?
Cu1 N8 2.0743(18) . ?
Cu1 Cl1 2.5822(6) . ?
N1 C5 1.339(3) . ?
N1 N2 1.356(3) . ?
N1 C6 1.444(3) . ?
N2 N3 1.278(3) . ?
N3 N4 1.363(3) . ?
N4 C5 1.349(3) . ?
N4 Cu1 2.0252(18) 3_656 ?
C6 C7 1.508(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 N8 1.461(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
N8 C9 1.461(3) . ?
N8 H8 0.94(3) . ?
C9 C10 1.503(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 N11 1.474(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
N11 H11A 0.89(3) . ?
N11 H11B 0.79(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
C5 Cu1 N4 92.94(8) . 3_656 ?
C5 Cu1 N11 162.06(9) . . ?
N4 Cu1 N11 90.47(8) 3_656 . ?
C5 Cu1 N8 92.71(8) . . ?
N4 Cu1 N8 169.97(7) 3_656 . ?
N11 Cu1 N8 81.66(8) . . ?
C5 Cu1 Cl1 105.96(6) . . ?
N4 Cu1 Cl1 97.82(5) 3_656 . ?
N11 Cu1 Cl1 90.99(7) . . ?
N8 Cu1 Cl1 88.58(5) . . ?
C5 N1 N2 111.7(2) . . ?
C5 N1 C6 128.8(2) . . ?
N2 N1 C6 119.5(2) . . ?
N3 N2 N1 106.1(2) . . ?
N2 N3 N4 109.67(19) . . ?
C5 N4 N3 108.89(18) . . ?
C5 N4 Cu1 133.19(15) . 3_656 ?
N3 N4 Cu1 117.62(14) . 3_656 ?
N1 C5 N4 103.60(19) . . ?
N1 C5 Cu1 122.76(16) . . ?
N4 C5 Cu1 133.64(16) . . ?
N1 C6 C7 111.8(2) . . ?
N1 C6 H6A 109.3 . . ?
C7 C6 H6A 109.3 . . ?
N1 C6 H6B 109.3 . . ?
C7 C6 H6B 109.3 . . ?
H6A C6 H6B 107.9 . . ?
N8 C7 C6 111.3(2) . . ?
N8 C7 H7A 109.4 . . ?
C6 C7 H7A 109.4 . . ?
N8 C7 H7B 109.4 . . ?
C6 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
C7 N8 C9 112.32(19) . . ?
C7 N8 Cu1 119.45(14) . . ?
C9 N8 Cu1 107.99(14) . . ?
C7 N8 H8 104.8(16) . . ?
C9 N8 H8 106.7(16) . . ?
Cu1 N8 H8 104.5(16) . . ?
N8 C9 C10 107.49(19) . . ?
N8 C9 H9A 110.2 . . ?
C10 C9 H9A 110.2 . . ?
N8 C9 H9B 110.2 . . ?
C10 C9 H9B 110.2 . . ?
H9A C9 H9B 108.5 . . ?
N11 C10 C9 106.5(2) . . ?
N11 C10 H10A 110.4 . . ?
C9 C10 H10A 110.4 . . ?
N11 C10 H10B 110.4 . . ?
C9 C10 H10B 110.4 . . ?
H10A C10 H10B 108.6 . . ?
C10 N11 Cu1 110.88(15) . . ?
C10 N11 H11A 106.8(19) . . ?
Cu1 N11 H11A 111.0(19) . . ?
C10 N11 H11B 110(2) . . ?
Cu1 N11 H11B 108(2) . . ?
H11A N11 H11B 110(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 N2 N3 -0.4(3) . . . . ?
C6 N1 N2 N3 179.8(3) . . . . ?
N1 N2 N3 N4 0.4(3) . . . . ?
N2 N3 N4 C5 -0.2(3) . . . . ?
N2 N3 N4 Cu1 -174.66(18) . . . 3_656 ?
N2 N1 C5 N4 0.3(3) . . . . ?
C6 N1 C5 N4 -179.9(3) . . . . ?
N2 N1 C5 Cu1 -179.36(17) . . . . ?
C6 N1 C5 Cu1 0.4(4) . . . . ?
N3 N4 C5 N1 -0.1(2) . . . . ?
Cu1 N4 C5 N1 173.20(16) 3_656 . . . ?
N3 N4 C5 Cu1 179.54(17) . . . . ?
Cu1 N4 C5 Cu1 -7.2(3) 3_656 . . . ?
C5 N1 C6 C7 -42.9(4) . . . . ?
N2 N1 C6 C7 136.8(3) . . . . ?
N1 C6 C7 N8 68.3(3) . . . . ?
C6 C7 N8 C9 179.4(2) . . . . ?
C6 C7 N8 Cu1 -52.6(3) . . . . ?
C7 N8 C9 C10 179.4(2) . . . . ?
Cu1 N8 C9 C10 45.6(2) . . . . ?
N8 C9 C10 N11 -55.1(2) . . . . ?
C9 C10 N11 Cu1 38.1(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
C6 H6A Cl1 0.97 2.66 3.550(3) 153. 1_455
N8 H8 Cl1 0.94(3) 2.80(3) 3.2719(19) 112.2(19) .
N8 H8 Cl1 0.94(3) 2.48(3) 3.2763(19) 143(2) 3_666
N11 H11A Cl1 0.89(3) 2.51(3) 3.328(2) 153(3) 4_566
N11 H11B N3 0.79(3) 2.53(3) 2.835(3) 105(3) 3_656

_refine_diff_density_max         0.753
_refine_diff_density_min         -0.430
_refine_diff_density_rms         0.074

####################################################################### 
# 
# 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_VI_100
_database_code_depnum_ccdc_archive 'CCDC 1484106'
_audit_update_record             
;
2016-06-08 deposited with the CCDC.
2016-07-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H24 Cl Cu N12, Cl'
_chemical_formula_sum            'C10 H24 Cl2 Cu N12'
_chemical_formula_weight         446.85

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   23.2189(3)
_cell_length_b                   10.4710(2)
_cell_length_c                   15.3156(2)
_cell_angle_alpha                90
_cell_angle_beta                 104.9566(6)
_cell_angle_gamma                90
_cell_volume                     3597.46(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9927
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      30.05

_exptl_crystal_description       lamina
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.650
_exptl_crystal_F_000             1848
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.525
_exptl_crystal_size_mid          0.388
_exptl_crystal_size_min          0.051
_exptl_absorpt_coefficient_mu    1.535
_shelx_estimated_absorpt_T_min   0.500
_shelx_estimated_absorpt_T_max   0.926
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5898
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            47046
_diffrn_reflns_av_unetI/netI     0.0119
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.816
_diffrn_reflns_theta_max         30.056
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5276
_reflns_number_gt                5016
_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       'APEX2 (Bruker, 2010)'
_computing_cell_refinement       'SAINT (Bruker, 2010)'
_computing_data_reduction        'SAINT (Bruker, 2010)'
_computing_structure_solution    'SIR2014 (Burla et al., 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  
;
SHELXL-2014/7 (Sheldrick, 2015),
PLATON (Spek, 2009)
;
_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)+(0.0278P)²+2.6474P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5276
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0185
_refine_ls_R_factor_gt           0.0173
_refine_ls_wR_factor_ref         0.0483
_refine_ls_wR_factor_gt          0.0476
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 0.25276(2) 0.51342(2) 0.38732(2) 0.00829(3) Uani 1 1 d . . . . .
Cl1 Cl 0.23358(2) 0.26875(2) 0.36164(2) 0.01209(5) Uani 1 1 d . . . . .
Cl2 Cl 0.28213(2) 0.80603(2) 0.38903(2) 0.01276(5) Uani 1 1 d . . . . .
N11 N 0.44091(3) 0.63047(8) 0.31506(5) 0.01212(14) Uani 1 1 d . . . . .
N12 N 0.49823(4) 0.65518(9) 0.35892(6) 0.01848(16) Uani 1 1 d . . . . .
N13 N 0.50335(4) 0.77843(9) 0.36297(7) 0.02248(18) Uani 1 1 d . . . . .
N14 N 0.45043(4) 0.83569(8) 0.32254(7) 0.02060(17) Uani 1 1 d . . . . .
C15 C 0.41263(4) 0.74171(9) 0.29335(7) 0.01582(17) Uani 1 1 d . . . . .
H15 H 0.3719 0.7514 0.2620 0.019 Uiso 1 1 calc R U . . .
C16 C 0.42031(4) 0.49870(8) 0.29761(6) 0.01254(16) Uani 1 1 d . . . . .
H16A H 0.4451 0.4421 0.3443 0.015 Uiso 1 1 calc R U . . .
H16B H 0.4252 0.4714 0.2381 0.015 Uiso 1 1 calc R U . . .
C17 C 0.35497(4) 0.48514(8) 0.29841(6) 0.01160(15) Uani 1 1 d . . . . .
H17A H 0.3306 0.5391 0.2496 0.014 Uiso 1 1 calc R U . . .
H17B H 0.3427 0.3953 0.2843 0.014 Uiso 1 1 calc R U . . .
N18 N 0.34145(3) 0.52048(7) 0.38403(5) 0.00999(13) Uani 1 1 d . . . . .
H18 H 0.3480(5) 0.5987(13) 0.3930(8) 0.012 Uiso 1 1 d . U . . .
C19 C 0.37503(4) 0.44650(9) 0.46320(6) 0.01423(16) Uani 1 1 d . . . . .
H19A H 0.4182 0.4645 0.4751 0.017 Uiso 1 1 calc R U . . .
H19B H 0.3686 0.3539 0.4518 0.017 Uiso 1 1 calc R U . . .
C110 C 0.35236(4) 0.48657(9) 0.54360(6) 0.01459(17) Uani 1 1 d . . . . .
H10A H 0.3689 0.4292 0.5954 0.018 Uiso 1 1 calc R U . . .
H10B H 0.3656 0.5747 0.5618 0.018 Uiso 1 1 calc R U . . .
N111 N 0.28659(3) 0.48033(7) 0.51911(5) 0.01050(13) Uani 1 1 d . . . . .
H11A H 0.2750(6) 0.4048(13) 0.5313(9) 0.013 Uiso 1 1 d . U . . .
H11B H 0.2718(6) 0.5341(13) 0.5492(9) 0.013 Uiso 1 1 d . U . . .
N21 N 0.05356(3) 0.61403(7) 0.45050(5) 0.01246(14) Uani 1 1 d . . . . .
N22 N 0.06554(4) 0.73775(8) 0.47286(6) 0.01787(16) Uani 1 1 d . . . . .
N23 N 0.02141(4) 0.80323(8) 0.42395(7) 0.02164(18) Uani 1 1 d . . . . .
N24 N -0.01942(4) 0.72515(9) 0.36944(7) 0.02074(17) Uani 1 1 d . . . . .
C25 C 0.00178(4) 0.60856(9) 0.38711(7) 0.01653(17) Uani 1 1 d . . . . .
H25 H -0.0168 0.5327 0.3593 0.020 Uiso 1 1 calc R U . . .
C26 C 0.09571(4) 0.51233(9) 0.48900(6) 0.01274(16) Uani 1 1 d . . . . .
H26A H 0.0732 0.4374 0.5019 0.015 Uiso 1 1 calc R U . . .
H26B H 0.1220 0.5422 0.5470 0.015 Uiso 1 1 calc R U . . .
C27 C 0.13414(4) 0.47139(8) 0.42668(6) 0.01178(15) Uani 1 1 d . . . . .
H27A H 0.1602 0.4001 0.4555 0.014 Uiso 1 1 calc R U . . .
H27B H 0.1078 0.4390 0.3695 0.014 Uiso 1 1 calc R U . . .
N28 N 0.17189(3) 0.57487(7) 0.40543(5) 0.00902(13) Uani 1 1 d . . . . .
H28 H 0.1817(5) 0.6233(13) 0.4501(9) 0.011 Uiso 1 1 d . U . . .
C29 C 0.14390(4) 0.64968(8) 0.32309(6) 0.01118(15) Uani 1 1 d . . . . .
H29A H 0.1619 0.7360 0.3274 0.013 Uiso 1 1 calc R U . . .
H29B H 0.1007 0.6592 0.3173 0.013 Uiso 1 1 calc R U . . .
C210 C 0.15381(4) 0.58025(9) 0.24115(6) 0.01176(15) Uani 1 1 d . . . . .
H10C H 0.1306 0.4999 0.2313 0.014 Uiso 1 1 calc R U . . .
H10D H 0.1402 0.6342 0.1866 0.014 Uiso 1 1 calc R U . . .
N211 N 0.21807(3) 0.55178(7) 0.25687(5) 0.00973(13) Uani 1 1 d . . . . .
H11C H 0.2231(6) 0.4887(12) 0.2234(9) 0.012 Uiso 1 1 d . U . . .
H11D H 0.2350(5) 0.6164(13) 0.2404(8) 0.012 Uiso 1 1 d . U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N211 1.9929(7) . ?
Cu1 N111 1.9981(8) . ?
Cu1 N28 2.0702(7) . ?
Cu1 N18 2.0742(8) . ?
Cu1 Cl1 2.6127(2) . ?
Cu1 Cl2 3.1375(2) . ?
N11 C15 1.3363(12) . ?
N11 N12 1.3521(11) . ?
N11 C16 1.4622(12) . ?
N12 N13 1.2961(13) . ?
N13 N14 1.3639(12) . ?
N14 C15 1.3177(13) . ?
C15 H15 0.9500 . ?
C16 C17 1.5270(12) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 N18 1.4722(11) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
N18 C19 1.4799(11) . ?
N18 H18 0.838(13) . ?
C19 C110 1.5179(13) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C110 N111 1.4769(12) . ?
C110 H10A 0.9900 . ?
C110 H10B 0.9900 . ?
N111 H11A 0.870(13) . ?
N111 H11B 0.854(13) . ?
N21 C25 1.3374(12) . ?
N21 N22 1.3505(11) . ?
N21 C26 1.4633(11) . ?
N22 N23 1.2980(12) . ?
N23 N24 1.3622(13) . ?
N24 C25 1.3181(13) . ?
C25 H25 0.9500 . ?
C26 C27 1.5267(12) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 N28 1.4816(11) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
N28 C29 1.4844(11) . ?
N28 H28 0.834(13) . ?
C29 C210 1.5184(12) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C210 N211 1.4791(11) . ?
C210 H10C 0.9900 . ?
C210 H10D 0.9900 . ?
N211 H11C 0.862(13) . ?
N211 H11D 0.853(14) . ?

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
N211 Cu1 N111 178.18(3) . . ?
N211 Cu1 N28 85.75(3) . . ?
N111 Cu1 N28 93.00(3) . . ?
N211 Cu1 N18 96.62(3) . . ?
N111 Cu1 N18 84.08(3) . . ?
N28 Cu1 N18 158.87(3) . . ?
N211 Cu1 Cl1 92.15(2) . . ?
N111 Cu1 Cl1 89.39(2) . . ?
N28 Cu1 Cl1 101.52(2) . . ?
N18 Cu1 Cl1 99.38(2) . . ?
N211 Cu1 Cl2 80.92(2) . . ?
N111 Cu1 Cl2 97.64(2) . . ?
N28 Cu1 Cl2 84.15(2) . . ?
N18 Cu1 Cl2 75.55(2) . . ?
Cl1 Cu1 Cl2 170.771(7) . . ?
C15 N11 N12 108.32(8) . . ?
C15 N11 C16 131.33(8) . . ?
N12 N11 C16 120.33(8) . . ?
N13 N12 N11 106.30(8) . . ?
N12 N13 N14 110.81(8) . . ?
C15 N14 N13 105.60(8) . . ?
N14 C15 N11 108.96(8) . . ?
N14 C15 H15 125.5 . . ?
N11 C15 H15 125.5 . . ?
N11 C16 C17 111.41(7) . . ?
N11 C16 H16A 109.3 . . ?
C17 C16 H16A 109.3 . . ?
N11 C16 H16B 109.3 . . ?
C17 C16 H16B 109.3 . . ?
H16A C16 H16B 108.0 . . ?
N18 C17 C16 115.12(7) . . ?
N18 C17 H17A 108.5 . . ?
C16 C17 H17A 108.5 . . ?
N18 C17 H17B 108.5 . . ?
C16 C17 H17B 108.5 . . ?
H17A C17 H17B 107.5 . . ?
C17 N18 C19 114.19(7) . . ?
C17 N18 Cu1 117.00(6) . . ?
C19 N18 Cu1 106.14(5) . . ?
C17 N18 H18 108.7(9) . . ?
C19 N18 H18 110.0(9) . . ?
Cu1 N18 H18 99.9(8) . . ?
N18 C19 C110 107.47(7) . . ?
N18 C19 H19A 110.2 . . ?
C110 C19 H19A 110.2 . . ?
N18 C19 H19B 110.2 . . ?
C110 C19 H19B 110.2 . . ?
H19A C19 H19B 108.5 . . ?
N111 C110 C19 109.52(7) . . ?
N111 C110 H10A 109.8 . . ?
C19 C110 H10A 109.8 . . ?
N111 C110 H10B 109.8 . . ?
C19 C110 H10B 109.8 . . ?
H10A C110 H10B 108.2 . . ?
C110 N111 Cu1 111.10(6) . . ?
C110 N111 H11A 110.0(8) . . ?
Cu1 N111 H11A 108.1(8) . . ?
C110 N111 H11B 111.6(9) . . ?
Cu1 N111 H11B 108.8(9) . . ?
H11A N111 H11B 107.1(12) . . ?
C25 N21 N22 108.23(8) . . ?
C25 N21 C26 130.07(8) . . ?
N22 N21 C26 121.56(8) . . ?
N23 N22 N21 106.27(8) . . ?
N22 N23 N24 110.95(8) . . ?
C25 N24 N23 105.43(8) . . ?
N24 C25 N21 109.12(9) . . ?
N24 C25 H25 125.4 . . ?
N21 C25 H25 125.4 . . ?
N21 C26 C27 112.98(7) . . ?
N21 C26 H26A 109.0 . . ?
C27 C26 H26A 109.0 . . ?
N21 C26 H26B 109.0 . . ?
C27 C26 H26B 109.0 . . ?
H26A C26 H26B 107.8 . . ?
N28 C27 C26 113.97(7) . . ?
N28 C27 H27A 108.8 . . ?
C26 C27 H27A 108.8 . . ?
N28 C27 H27B 108.8 . . ?
C26 C27 H27B 108.8 . . ?
H27A C27 H27B 107.7 . . ?
C27 N28 C29 114.74(7) . . ?
C27 N28 Cu1 114.24(5) . . ?
C29 N28 Cu1 105.28(5) . . ?
C27 N28 H28 108.5(8) . . ?
C29 N28 H28 110.1(9) . . ?
Cu1 N28 H28 103.4(8) . . ?
N28 C29 C210 108.84(7) . . ?
N28 C29 H29A 109.9 . . ?
C210 C29 H29A 109.9 . . ?
N28 C29 H29B 109.9 . . ?
C210 C29 H29B 109.9 . . ?
H29A C29 H29B 108.3 . . ?
N211 C210 C29 108.88(7) . . ?
N211 C210 H10C 109.9 . . ?
C29 C210 H10C 109.9 . . ?
N211 C210 H10D 109.9 . . ?
C29 C210 H10D 109.9 . . ?
H10C C210 H10D 108.3 . . ?
C210 N211 Cu1 109.48(5) . . ?
C210 N211 H11C 110.1(9) . . ?
Cu1 N211 H11C 111.1(9) . . ?
C210 N211 H11D 108.3(8) . . ?
Cu1 N211 H11D 111.0(8) . . ?
H11C N211 H11D 106.8(12) . . ?

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
C15 N11 N12 N13 0.14(11) . . . . ?
C16 N11 N12 N13 178.95(8) . . . . ?
N11 N12 N13 N14 -0.02(11) . . . . ?
N12 N13 N14 C15 -0.11(12) . . . . ?
N13 N14 C15 N11 0.19(11) . . . . ?
N12 N11 C15 N14 -0.21(11) . . . . ?
C16 N11 C15 N14 -178.85(9) . . . . ?
C15 N11 C16 C17 -33.41(13) . . . . ?
N12 N11 C16 C17 148.09(8) . . . . ?
N11 C16 C17 N18 -60.10(10) . . . . ?
C16 C17 N18 C19 -58.37(10) . . . . ?
C16 C17 N18 Cu1 176.83(6) . . . . ?
C17 N18 C19 C110 -175.41(7) . . . . ?
Cu1 N18 C19 C110 -45.02(8) . . . . ?
N18 C19 C110 N111 50.09(10) . . . . ?
C19 C110 N111 Cu1 -29.74(9) . . . . ?
C25 N21 N22 N23 0.42(11) . . . . ?
C26 N21 N22 N23 176.51(8) . . . . ?
N21 N22 N23 N24 -0.21(11) . . . . ?
N22 N23 N24 C25 -0.08(12) . . . . ?
N23 N24 C25 N21 0.35(12) . . . . ?
N22 N21 C25 N24 -0.49(11) . . . . ?
C26 N21 C25 N24 -176.13(9) . . . . ?
C25 N21 C26 C27 77.20(12) . . . . ?
N22 N21 C26 C27 -97.94(10) . . . . ?
N21 C26 C27 N28 61.04(10) . . . . ?
C26 C27 N28 C29 -91.01(9) . . . . ?
C26 C27 N28 Cu1 147.28(6) . . . . ?
C27 N28 C29 C210 -84.70(8) . . . . ?
Cu1 N28 C29 C210 41.78(7) . . . . ?
N28 C29 C210 N211 -52.01(9) . . . . ?
C29 C210 N211 Cu1 34.87(8) . . . . ?

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
C15 H15 Cl1 0.95 2.69 3.6166(10) 166. 4
C16 H16A N23 0.99 2.37 3.3315(13) 163. 3_545
C16 H16A N24 0.99 2.41 3.2524(13) 142. 3_545
N18 H18 Cl2 0.838(13) 2.648(13) 3.3012(8) 135.9(10) .
N111 H11A Cl1 0.870(13) 2.491(13) 3.2862(8) 152.3(11) 7_556
N111 H11B Cl2 0.854(13) 2.424(13) 3.2694(8) 170.5(12) 7_566
C25 H25 N14 0.95 2.22 3.1551(13) 167. 3_445
C26 H26B Cl2 0.99 2.70 3.5239(10) 140. 7_566
N28 H28 Cl2 0.834(13) 2.501(13) 3.2970(8) 159.8(12) 7_566
C29 H29B N21 0.99 2.59 3.2341(11) 122. .
C210 H10C N14 0.99 2.52 3.4855(12) 164. 4_545
N211 H11D Cl1 0.853(14) 2.471(13) 3.2814(8) 159.0(11) 4
N211 H11C Cl2 0.862(13) 2.556(14) 3.4072(8) 169.7(12) 4_545

_refine_diff_density_max         0.445
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.052

####################################################################### 
# 
# 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_VI_296
_database_code_depnum_ccdc_archive 'CCDC 1484107'
_audit_update_record             
;
2016-06-08 deposited with the CCDC.
2016-07-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H24 Cl Cu N12, Cl'
_chemical_formula_sum            'C10 H24 Cl2 Cu N12'
_chemical_formula_weight         446.85

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   23.4624(4)
_cell_length_b                   10.4593(2)
_cell_length_c                   15.5341(2)
_cell_angle_alpha                90
_cell_angle_beta                 105.3813(7)
_cell_angle_gamma                90
_cell_volume                     3675.53(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9906
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      30.03

_exptl_crystal_description       lamina
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.615
_exptl_crystal_F_000             1848
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.525
_exptl_crystal_size_mid          0.388
_exptl_crystal_size_min          0.051
_exptl_absorpt_coefficient_mu    1.502
_shelx_estimated_absorpt_T_min   0.506
_shelx_estimated_absorpt_T_max   0.927
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6113
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24979
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.800
_diffrn_reflns_theta_max         30.097
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5390
_reflns_number_gt                4501
_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       'APEX2 (Bruker, 2010)'
_computing_cell_refinement       'SAINT (Bruker, 2010)'
_computing_data_reduction        'SAINT (Bruker, 2010)'
_computing_structure_solution    'SIR2014 (Burla et al., 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  
;
SHELXL-2014/7 (Sheldrick, 2015),
PLATON (Spek, 2009)
;
_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)+(0.0354P)²+1.4827P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5390
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0256
_refine_ls_wR_factor_ref         0.0679
_refine_ls_wR_factor_gt          0.0633
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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 0.25282(2) 0.48844(2) 0.38725(2) 0.02452(5) Uani 1 1 d . . . . .
Cl1 Cl 0.23461(2) 0.73546(3) 0.36141(2) 0.03530(9) Uani 1 1 d . . . . .
Cl2 Cl 0.28130(2) 0.19457(3) 0.39045(2) 0.03648(9) Uani 1 1 d . . . . .
N11 N 0.44015(5) 0.37605(12) 0.31645(8) 0.0342(3) Uani 1 1 d . . . . .
N12 N 0.49688(6) 0.35252(17) 0.35991(12) 0.0562(4) Uani 1 1 d . . . . .
N13 N 0.50244(7) 0.22971(18) 0.36301(14) 0.0690(5) Uani 1 1 d . . . . .
N14 N 0.45083(8) 0.17152(15) 0.32220(14) 0.0630(5) Uani 1 1 d . . . . .
C15 C 0.41346(8) 0.26442(16) 0.29398(13) 0.0460(4) Uani 1 1 d . . . . .
H15 H 0.3740 0.2540 0.2628 0.055 Uiso 1 1 calc R U . . .
C16 C 0.41859(7) 0.50671(13) 0.29946(10) 0.0346(3) Uani 1 1 d . . . . .
H16A H 0.4228 0.5343 0.2419 0.041 Uiso 1 1 calc R U . . .
H16B H 0.4424 0.5628 0.3447 0.041 Uiso 1 1 calc R U . . .
C17 C 0.35403(6) 0.51785(14) 0.30027(9) 0.0317(3) Uani 1 1 d . . . . .
H17A H 0.3415 0.6056 0.2867 0.038 Uiso 1 1 calc R U . . .
H17B H 0.3306 0.4647 0.2528 0.038 Uiso 1 1 calc R U . . .
N18 N 0.34067(5) 0.48144(11) 0.38422(8) 0.0264(2) Uani 1 1 d . . . . .
H18 H 0.3476(7) 0.4099(16) 0.3926(11) 0.032 Uiso 1 1 d . U . . .
C19 C 0.37423(7) 0.55249(17) 0.46342(10) 0.0386(3) Uani 1 1 d . . . . .
H19A H 0.3686 0.6437 0.4536 0.046 Uiso 1 1 calc R U . . .
H19B H 0.4161 0.5338 0.4751 0.046 Uiso 1 1 calc R U . . .
C110 C 0.35180(7) 0.51140(17) 0.54171(10) 0.0408(4) Uani 1 1 d . . . . .
H10A H 0.3643 0.4244 0.5584 0.049 Uiso 1 1 calc R U . . .
H10B H 0.3682 0.5664 0.5925 0.049 Uiso 1 1 calc R U . . .
N111 N 0.28707(6) 0.51898(12) 0.51755(7) 0.0286(2) Uani 1 1 d . . . . .
H11A H 0.2758(7) 0.5911(17) 0.5295(11) 0.034 Uiso 1 1 d . U . . .
H11B H 0.2721(7) 0.4657(16) 0.5473(11) 0.034 Uiso 1 1 d . U . . .
N21 N 0.05487(5) 0.39102(12) 0.44865(8) 0.0343(3) Uani 1 1 d . . . . .
N22 N 0.06614(7) 0.26738(14) 0.46934(12) 0.0536(4) Uani 1 1 d . . . . .
N23 N 0.02154(8) 0.20365(16) 0.42179(14) 0.0666(5) Uani 1 1 d . . . . .
N24 N -0.01881(7) 0.28293(16) 0.37014(14) 0.0617(4) Uani 1 1 d . . . . .
C25 C 0.00316(7) 0.39747(17) 0.38816(13) 0.0481(4) Uani 1 1 d . . . . .
H25 H -0.0148 0.4725 0.3624 0.058 Uiso 1 1 calc R U . . .
C26 C 0.09741(7) 0.49121(14) 0.48693(10) 0.0346(3) Uani 1 1 d . . . . .
H26A H 0.1230 0.4608 0.5429 0.042 Uiso 1 1 calc R U . . .
H26B H 0.0762 0.5652 0.4999 0.042 Uiso 1 1 calc R U . . .
C27 C 0.13535(6) 0.53190(13) 0.42596(10) 0.0315(3) Uani 1 1 d . . . . .
H27A H 0.1097 0.5648 0.3708 0.038 Uiso 1 1 calc R U . . .
H27B H 0.1610 0.6012 0.4544 0.038 Uiso 1 1 calc R U . . .
N28 N 0.17219(5) 0.42887(11) 0.40408(7) 0.0250(2) Uani 1 1 d . . . . .
H28 H 0.1816(7) 0.3812(16) 0.4451(10) 0.030 Uiso 1 1 d . U . . .
C29 C 0.14404(6) 0.35528(13) 0.32222(9) 0.0303(3) Uani 1 1 d . . . . .
H29A H 0.1020 0.3470 0.3161 0.036 Uiso 1 1 calc R U . . .
H29B H 0.1610 0.2702 0.3261 0.036 Uiso 1 1 calc R U . . .
C210 C 0.15425(6) 0.42483(14) 0.24234(9) 0.0323(3) Uani 1 1 d . . . . .
H10C H 0.1407 0.3726 0.1892 0.039 Uiso 1 1 calc R U . . .
H10D H 0.1322 0.5043 0.2331 0.039 Uiso 1 1 calc R U . . .
N211 N 0.21788(5) 0.45156(12) 0.25835(7) 0.0259(2) Uani 1 1 d . . . . .
H11C H 0.2233(7) 0.5146(16) 0.2255(11) 0.031 Uiso 1 1 d . U . . .
H11D H 0.2341(7) 0.3879(16) 0.2423(10) 0.031 Uiso 1 1 d . U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N211 1.9897(11) . ?
Cu1 N111 1.9955(11) . ?
Cu1 N28 2.0732(11) . ?
Cu1 N18 2.0753(12) . ?
Cu1 Cl1 2.6321(4) . ?
Cu1 Cl2 3.1430(4) . ?
N11 C15 1.327(2) . ?
N11 N12 1.3457(19) . ?
N11 C16 1.4569(18) . ?
N12 N13 1.291(2) . ?
N13 N14 1.353(2) . ?
N14 C15 1.304(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.522(2) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 N18 1.4700(16) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
N18 C19 1.4737(18) . ?
N18 H18 0.769(17) . ?
C19 C110 1.510(2) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C110 N111 1.467(2) . ?
C110 H10A 0.9700 . ?
C110 H10B 0.9700 . ?
N111 H11A 0.837(17) . ?
N111 H11B 0.857(17) . ?
N21 C25 1.325(2) . ?
N21 N22 1.3419(18) . ?
N21 C26 1.4605(19) . ?
N22 N23 1.294(2) . ?
N23 N24 1.351(3) . ?
N24 C25 1.305(2) . ?
C25 H25 0.9300 . ?
C26 C27 1.5225(18) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 N28 1.4763(16) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
N28 C29 1.4833(16) . ?
N28 H28 0.792(16) . ?
C29 C210 1.5112(19) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C210 N211 1.4738(17) . ?
C210 H10C 0.9700 . ?
C210 H10D 0.9700 . ?
N211 H11C 0.864(17) . ?
N211 H11D 0.837(17) . ?

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
N211 Cu1 N111 177.91(5) . . ?
N211 Cu1 N28 85.55(4) . . ?
N111 Cu1 N28 93.19(5) . . ?
N211 Cu1 N18 96.72(4) . . ?
N111 Cu1 N18 83.89(5) . . ?
N28 Cu1 N18 159.60(5) . . ?
N211 Cu1 Cl1 91.72(4) . . ?
N111 Cu1 Cl1 90.17(4) . . ?
N28 Cu1 Cl1 101.40(3) . . ?
N18 Cu1 Cl1 98.81(3) . . ?
N211 Cu1 Cl2 81.69(4) . . ?
N111 Cu1 Cl2 96.53(4) . . ?
N28 Cu1 Cl2 84.34(3) . . ?
N18 Cu1 Cl2 75.98(3) . . ?
Cl1 Cu1 Cl2 170.955(11) . . ?
C15 N11 N12 107.82(14) . . ?
C15 N11 C16 131.34(13) . . ?
N12 N11 C16 120.81(13) . . ?
N13 N12 N11 106.11(15) . . ?
N12 N13 N14 111.16(15) . . ?
C15 N14 N13 105.11(16) . . ?
N14 C15 N11 109.80(16) . . ?
N14 C15 H15 125.1 . . ?
N11 C15 H15 125.1 . . ?
N11 C16 C17 111.64(11) . . ?
N11 C16 H16A 109.3 . . ?
C17 C16 H16A 109.3 . . ?
N11 C16 H16B 109.3 . . ?
C17 C16 H16B 109.3 . . ?
H16A C16 H16B 108.0 . . ?
N18 C17 C16 115.74(12) . . ?
N18 C17 H17A 108.3 . . ?
C16 C17 H17A 108.3 . . ?
N18 C17 H17B 108.3 . . ?
C16 C17 H17B 108.3 . . ?
H17A C17 H17B 107.4 . . ?
C17 N18 C19 114.68(11) . . ?
C17 N18 Cu1 117.24(9) . . ?
C19 N18 Cu1 106.10(8) . . ?
C17 N18 H18 108.4(12) . . ?
C19 N18 H18 107.9(12) . . ?
Cu1 N18 H18 101.4(12) . . ?
N18 C19 C110 107.80(12) . . ?
N18 C19 H19A 110.1 . . ?
C110 C19 H19A 110.1 . . ?
N18 C19 H19B 110.1 . . ?
C110 C19 H19B 110.1 . . ?
H19A C19 H19B 108.5 . . ?
N111 C110 C19 109.69(12) . . ?
N111 C110 H10A 109.7 . . ?
C19 C110 H10A 109.7 . . ?
N111 C110 H10B 109.7 . . ?
C19 C110 H10B 109.7 . . ?
H10A C110 H10B 108.2 . . ?
C110 N111 Cu1 111.22(9) . . ?
C110 N111 H11A 111.1(12) . . ?
Cu1 N111 H11A 107.7(11) . . ?
C110 N111 H11B 111.9(11) . . ?
Cu1 N111 H11B 109.3(11) . . ?
H11A N111 H11B 105.5(15) . . ?
C25 N21 N22 107.72(13) . . ?
C25 N21 C26 130.59(14) . . ?
N22 N21 C26 121.60(13) . . ?
N23 N22 N21 106.34(15) . . ?
N22 N23 N24 110.86(15) . . ?
C25 N24 N23 105.15(16) . . ?
N24 C25 N21 109.93(16) . . ?
N24 C25 H25 125.0 . . ?
N21 C25 H25 125.0 . . ?
N21 C26 C27 113.37(12) . . ?
N21 C26 H26A 108.9 . . ?
C27 C26 H26A 108.9 . . ?
N21 C26 H26B 108.9 . . ?
C27 C26 H26B 108.9 . . ?
H26A C26 H26B 107.7 . . ?
N28 C27 C26 114.44(11) . . ?
N28 C27 H27A 108.6 . . ?
C26 C27 H27A 108.6 . . ?
N28 C27 H27B 108.6 . . ?
C26 C27 H27B 108.6 . . ?
H27A C27 H27B 107.6 . . ?
C27 N28 C29 114.93(11) . . ?
C27 N28 Cu1 114.78(8) . . ?
C29 N28 Cu1 105.16(7) . . ?
C27 N28 H28 109.2(11) . . ?
C29 N28 H28 109.1(12) . . ?
Cu1 N28 H28 102.8(11) . . ?
N28 C29 C210 108.82(11) . . ?
N28 C29 H29A 109.9 . . ?
C210 C29 H29A 109.9 . . ?
N28 C29 H29B 109.9 . . ?
C210 C29 H29B 109.9 . . ?
H29A C29 H29B 108.3 . . ?
N211 C210 C29 109.08(11) . . ?
N211 C210 H10C 109.9 . . ?
C29 C210 H10C 109.9 . . ?
N211 C210 H10D 109.9 . . ?
C29 C210 H10D 109.9 . . ?
H10C C210 H10D 108.3 . . ?
C210 N211 Cu1 109.58(8) . . ?
C210 N211 H11C 110.3(11) . . ?
Cu1 N211 H11C 111.1(11) . . ?
C210 N211 H11D 108.6(11) . . ?
Cu1 N211 H11D 110.8(11) . . ?
H11C N211 H11D 106.4(15) . . ?

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
C15 N11 N12 N13 -0.6(2) . . . . ?
C16 N11 N12 N13 -178.87(15) . . . . ?
N11 N12 N13 N14 0.3(2) . . . . ?
N12 N13 N14 C15 0.0(2) . . . . ?
N13 N14 C15 N11 -0.4(2) . . . . ?
N12 N11 C15 N14 0.6(2) . . . . ?
C16 N11 C15 N14 178.66(16) . . . . ?
C15 N11 C16 C17 34.5(2) . . . . ?
N12 N11 C16 C17 -147.67(14) . . . . ?
N11 C16 C17 N18 60.03(16) . . . . ?
C16 C17 N18 C19 56.80(16) . . . . ?
C16 C17 N18 Cu1 -177.77(9) . . . . ?
C17 N18 C19 C110 175.49(12) . . . . ?
Cu1 N18 C19 C110 44.43(14) . . . . ?
N18 C19 C110 N111 -49.93(17) . . . . ?
C19 C110 N111 Cu1 29.92(15) . . . . ?
C25 N21 N22 N23 -0.2(2) . . . . ?
C26 N21 N22 N23 -177.06(15) . . . . ?
N21 N22 N23 N24 0.1(2) . . . . ?
N22 N23 N24 C25 0.1(3) . . . . ?
N23 N24 C25 N21 -0.3(2) . . . . ?
N22 N21 C25 N24 0.3(2) . . . . ?
C26 N21 C25 N24 176.75(15) . . . . ?
C25 N21 C26 C27 -78.7(2) . . . . ?
N22 N21 C26 C27 97.34(17) . . . . ?
N21 C26 C27 N28 -61.17(18) . . . . ?
C26 C27 N28 C29 90.90(15) . . . . ?
C26 C27 N28 Cu1 -146.95(10) . . . . ?
C27 N28 C29 C210 85.43(13) . . . . ?
Cu1 N28 C29 C210 -41.78(12) . . . . ?
N28 C29 C210 N211 52.12(14) . . . . ?
C29 C210 N211 Cu1 -34.96(13) . . . . ?

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
C15 H15 Cl1 0.93 2.77 3.6796(19) 168. 4_545
C16 H16B N23 0.97 2.42 3.355(2) 161. 3
C16 H16B N24 0.97 2.47 3.295(2) 143. 3
N18 H18 Cl2 0.769(17) 2.733(17) 3.3203(12) 134.8(15) .
N111 H11A Cl1 0.837(17) 2.537(17) 3.3013(12) 152.3(15) 7_566
N111 H11B Cl2 0.857(17) 2.441(17) 3.2894(13) 171.0(15) 7_556
C25 H25 N14 0.93 2.26 3.179(2) 170. 3_455
C26 H26A Cl2 0.97 2.74 3.5536(17) 142. 7_556
N28 H28 Cl2 0.792(16) 2.595(16) 3.3463(11) 158.8(15) 7_556
C29 H29A N21 0.97 2.62 3.2488(17) 122. .
C210 H10D N14 0.97 2.59 3.526(2) 163. 4
N211 H11C Cl2 0.864(17) 2.588(17) 3.4391(12) 168.8(15) 4
N211 H11D Cl1 0.837(17) 2.511(17) 3.3033(12) 158.4(14) 4_545

_refine_diff_density_max         0.474
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.051

