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

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

data_d297
_database_code_depnum_ccdc_archive 'CCDC 958913'
_audit_update_record             
;
2014-11-17 deposited with the CCDC.
2015-03-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H20 Cu4 I4 N8'
_chemical_formula_weight         1122.19

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-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                   21.494(4)
_cell_length_b                   8.3309(14)
_cell_length_c                   18.367(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 121.704(3)
_cell_angle_gamma                90.00
_cell_volume                     2798.2(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    793
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      27.43

_exptl_crystal_description       PLATE
_exptl_crystal_colour            YELLOW
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      'Not Measured'
_exptl_crystal_density_diffrn    2.664
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2072
_exptl_absorpt_coefficient_mu    7.437
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.4219
_exptl_absorpt_correction_T_max  0.6662
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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            9555
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_av_unetI/netI     0.0485
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.23
_diffrn_reflns_theta_max         27.50
_reflns_number_total             3191
_reflns_number_gt                2701
_reflns_threshold_expression     >2sigma(I)

_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-97 (Sheldrick, 1997)'
_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. 
;

_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)+(0.0611P)²+4.9581P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3191
_refine_ls_number_parameters     159
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0369
_refine_ls_wR_factor_ref         0.1201
_refine_ls_wR_factor_gt          0.1006
_refine_ls_goodness_of_fit_ref   1.162
_refine_ls_restrained_S_all      1.162
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.67700(5) 0.32709(10) 0.08204(5) 0.0144(2) Uani 1 1 d . . .
Cu2 Cu 0.69419(5) 0.35106(10) -0.04979(5) 0.0157(2) Uani 1 1 d . . .
I1 I 0.63058(3) 0.57463(5) -0.01290(3) 0.01634(15) Uani 1 1 d . . .
I2 I 0.66297(2) 0.06336(5) -0.01096(3) 0.01444(14) Uani 1 1 d . . .
N1 N 0.6395(3) 0.2587(7) 0.1606(4) 0.0158(12) Uani 1 1 d . . .
N2 N 0.8034(3) 0.2741(7) 0.2611(3) 0.0115(11) Uani 1 1 d . . .
N3 N 0.7825(3) 0.2761(7) 0.1799(3) 0.0114(11) Uani 1 1 d . . .
N4 N 0.8315(3) 0.1924(7) 0.1723(4) 0.0132(12) Uani 1 1 d . . .
C1 C 0.5745(4) 0.1833(9) 0.1252(4) 0.0173(15) Uani 1 1 d U . .
H1 H 0.5425 0.1861 0.0648 0.021 Uiso 1 1 calc R . .
C2 C 0.5521(4) 0.1004(9) 0.1745(5) 0.0248(17) Uani 1 1 d . . .
H2 H 0.5057 0.0490 0.1475 0.030 Uiso 1 1 calc R . .
C3 C 0.5972(4) 0.0946(9) 0.2605(5) 0.0216(16) Uani 1 1 d . . .
H3 H 0.5833 0.0370 0.2944 0.026 Uiso 1 1 calc R . .
C4 C 0.6643(4) 0.1740(9) 0.2990(5) 0.0182(15) Uani 1 1 d . . .
H4 H 0.6964 0.1718 0.3594 0.022 Uiso 1 1 calc R . .
C5 C 0.6835(4) 0.2549(8) 0.2488(4) 0.0132(14) Uani 1 1 d . . .
C6 C 0.7550(4) 0.3440(8) 0.2878(4) 0.0139(14) Uani 1 1 d . . .
H6A H 0.7453 0.4580 0.2701 0.017 Uiso 1 1 calc R . .
H6B H 0.7800 0.3400 0.3509 0.017 Uiso 1 1 calc R . .
C7 C 0.8665(4) 0.1895(8) 0.3081(5) 0.0169(15) Uani 1 1 d . . .
H7 H 0.8929 0.1709 0.3681 0.020 Uiso 1 1 calc R . .
C8 C 0.8838(4) 0.1369(8) 0.2498(4) 0.0130(14) Uani 1 1 d . . .
C9 C 0.9466(4) 0.0433(8) 0.2597(4) 0.0124(14) Uani 1 1 d . . .
H9A H 0.9279 -0.0432 0.2163 0.015 Uiso 1 1 calc R . .
H9B H 0.9726 -0.0078 0.3169 0.015 Uiso 1 1 calc R . .
C10 C 1.0000 0.1453(12) 0.2500 0.014(2) Uani 1 2 d S . .
H10A H 0.9726 0.2152 0.1991 0.017 Uiso 0.50 1 calc PR . .
H10B H 1.0274 0.2152 0.3009 0.017 Uiso 0.50 1 calc PR . .


_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 N3 2.067(6) . ?
Cu1 N1 2.069(6) . ?
Cu1 I1 2.5418(10) . ?
Cu1 Cu2 2.6420(12) . ?
Cu1 I2 2.7009(10) . ?
Cu2 N4 2.047(6) 7_655 ?
Cu2 I1 2.6021(10) . ?
Cu2 I2 2.6844(10) . ?
Cu2 Cu2 2.7064(17) 7_655 ?
Cu2 I2 2.7530(11) 7_655 ?
I2 Cu2 2.7530(11) 7_655 ?
N1 C1 1.347(9) . ?
N1 C5 1.382(9) . ?
N2 N3 1.311(7) . ?
N2 C7 1.361(9) . ?
N2 C6 1.483(9) . ?
N3 N4 1.331(8) . ?
N4 C8 1.350(9) . ?
N4 Cu2 2.047(6) 7_655 ?
C1 C2 1.409(10) . ?
C1 H1 0.9500 . ?
C2 C3 1.352(11) . ?
C2 H2 0.9500 . ?
C3 C4 1.395(11) . ?
C3 H3 0.9500 . ?
C4 C5 1.369(10) . ?
C4 H4 0.9500 . ?
C5 C6 1.506(10) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.375(10) . ?
C7 H7 0.9500 . ?
C8 C9 1.486(9) . ?
C9 C10 1.512(9) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C9 1.512(9) 2_755 ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?

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 N1 89.3(2) . . ?
N3 Cu1 I1 128.27(16) . . ?
N1 Cu1 I1 123.06(17) . . ?
N3 Cu1 Cu2 101.24(16) . . ?
N1 Cu1 Cu2 162.47(17) . . ?
I1 Cu1 Cu2 60.23(3) . . ?
N3 Cu1 I2 95.15(16) . . ?
N1 Cu1 I2 105.20(17) . . ?
I1 Cu1 I2 110.67(3) . . ?
Cu2 Cu1 I2 60.31(3) . . ?
N4 Cu2 I1 122.51(16) 7_655 . ?
N4 Cu2 Cu1 155.08(16) 7_655 . ?
I1 Cu2 Cu1 57.98(3) . . ?
N4 Cu2 I2 99.99(16) 7_655 . ?
I1 Cu2 I2 109.33(4) . . ?
Cu1 Cu2 I2 60.93(3) . . ?
N4 Cu2 Cu2 105.31(16) 7_655 7_655 ?
I1 Cu2 Cu2 132.06(5) . 7_655 ?
Cu1 Cu2 Cu2 80.50(4) . 7_655 ?
I2 Cu2 Cu2 61.42(4) . 7_655 ?
N4 Cu2 I2 95.19(16) 7_655 7_655 ?
I1 Cu2 I2 109.62(4) . 7_655 ?
Cu1 Cu2 I2 108.14(4) . 7_655 ?
I2 Cu2 I2 120.32(3) . 7_655 ?
Cu2 Cu2 I2 58.90(4) 7_655 7_655 ?
Cu1 I1 Cu2 61.80(3) . . ?
Cu2 I2 Cu1 58.76(3) . . ?
Cu2 I2 Cu2 59.68(3) . 7_655 ?
Cu1 I2 Cu2 78.63(3) . 7_655 ?
C1 N1 C5 116.9(6) . . ?
C1 N1 Cu1 118.5(5) . . ?
C5 N1 Cu1 123.1(5) . . ?
N3 N2 C7 111.1(6) . . ?
N3 N2 C6 119.4(5) . . ?
C7 N2 C6 129.2(6) . . ?
N2 N3 N4 107.2(5) . . ?
N2 N3 Cu1 123.7(4) . . ?
N4 N3 Cu1 125.7(4) . . ?
N3 N4 C8 109.5(5) . . ?
N3 N4 Cu2 115.9(4) . 7_655 ?
C8 N4 Cu2 133.9(5) . 7_655 ?
N1 C1 C2 122.4(7) . . ?
N1 C1 H1 118.8 . . ?
C2 C1 H1 118.8 . . ?
C3 C2 C1 119.4(7) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C2 C3 C4 119.4(7) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C5 C4 C3 119.2(7) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C4 C5 N1 122.6(7) . . ?
C4 C5 C6 121.0(6) . . ?
N1 C5 C6 116.4(6) . . ?
N2 C6 C5 111.6(5) . . ?
N2 C6 H6A 109.3 . . ?
C5 C6 H6A 109.3 . . ?
N2 C6 H6B 109.3 . . ?
C5 C6 H6B 109.3 . . ?
H6A C6 H6B 108.0 . . ?
N2 C7 C8 104.9(6) . . ?
N2 C7 H7 127.5 . . ?
C8 C7 H7 127.5 . . ?
N4 C8 C7 107.3(6) . . ?
N4 C8 C9 120.5(6) . . ?
C7 C8 C9 132.2(6) . . ?
C8 C9 C10 112.8(6) . . ?
C8 C9 H9A 109.0 . . ?
C10 C9 H9A 109.0 . . ?
C8 C9 H9B 109.0 . . ?
C10 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
C9 C10 C9 111.6(8) 2_755 . ?
C9 C10 H10A 109.3 2_755 . ?
C9 C10 H10A 109.3 . . ?
C9 C10 H10B 109.3 2_755 . ?
C9 C10 H10B 109.3 . . ?
H10A C10 H10B 108.0 . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         1.492
_refine_diff_density_min         -1.435
_refine_diff_density_rms         0.317
####################################################################### 
# 
# 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_d259
_database_code_depnum_ccdc_archive 'CCDC 958914'
_audit_update_record             
;
2014-11-17 deposited with the CCDC.
2015-03-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H28 Cu4 I4 N10'
_chemical_formula_weight         1218.32

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'
I I -0.4742 1.8119 '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                   18.283(5)
_cell_length_b                   8.628(2)
_cell_length_c                   21.554(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.845(5)
_cell_angle_gamma                90.00
_cell_volume                     3368.2(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    821
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      27.23

_exptl_crystal_description       Thin_Plate
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      'Not Measured'
_exptl_crystal_density_diffrn    2.403
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2280
_exptl_absorpt_coefficient_mu    6.191
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.1478
_exptl_absorpt_correction_T_max  0.8862
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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            21954
_diffrn_reflns_av_R_equivalents  0.0572
_diffrn_reflns_av_unetI/netI     0.0669
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.12
_diffrn_reflns_theta_max         27.50
_reflns_number_total             7719
_reflns_number_gt                5875
_reflns_threshold_expression     >2sigma(I)

_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-97 (Sheldrick, 1997)'
_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. 
;

_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)+(0.0701P)²+11.3516P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7719
_refine_ls_number_parameters     408
_refine_ls_number_restraints     209
_refine_ls_R_factor_all          0.0698
_refine_ls_R_factor_gt           0.0526
_refine_ls_wR_factor_ref         0.1462
_refine_ls_wR_factor_gt          0.1355
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N2S N 0.6310(6) 0.5741(12) 0.4792(5) 0.0449(18) Uani 0.833(7) 1 d PDU A 1
C3S C 0.6874(6) 0.6289(15) 0.4871(5) 0.0444(18) Uani 0.833(7) 1 d PDU A 1
C4S C 0.7622(6) 0.7017(17) 0.4974(7) 0.0444(18) Uani 0.833(7) 1 d PDU A 1
H4S1 H 0.7855 0.6918 0.4592 0.067 Uiso 0.833(7) 1 calc PR A 1
H4S2 H 0.7927 0.6495 0.5321 0.067 Uiso 0.833(7) 1 calc PR A 1
H4S3 H 0.7575 0.8117 0.5075 0.067 Uiso 0.833(7) 1 calc PR A 1
N2X N 0.874(2) 0.610(6) 0.519(2) 0.044(2) Uani 0.167(7) 1 d PDU A 2
C1X C 0.815(3) 0.638(8) 0.513(3) 0.0445(19) Uani 0.167(7) 1 d PDU A 2
C2X C 0.740(3) 0.712(10) 0.504(3) 0.0444(19) Uani 0.167(7) 1 d PDU A 2
H2X1 H 0.7018 0.6322 0.5039 0.067 Uiso 0.167(7) 1 calc PR A 2
H2X2 H 0.7327 0.7694 0.4648 0.067 Uiso 0.167(7) 1 calc PR A 2
H2X3 H 0.7364 0.7840 0.5392 0.067 Uiso 0.167(7) 1 calc PR A 2
Cu1 Cu 0.86553(4) 0.31264(10) 0.18821(4) 0.01481(19) Uani 1 1 d U . .
Cu2 Cu 0.72237(5) 0.33595(11) 0.19295(4) 0.0185(2) Uani 1 1 d U . .
Cu3 Cu 0.77778(5) 0.13303(11) 0.30041(4) 0.0192(2) Uani 1 1 d U . .
Cu4 Cu 0.63537(5) 0.16246(10) 0.30593(4) 0.0156(2) Uani 1 1 d U . .
I1 I 0.78371(2) 0.05704(5) 0.17417(2) 0.01613(13) Uani 1 1 d U . .
I2 I 0.71759(2) 0.41519(5) 0.31670(2) 0.01578(13) Uani 1 1 d U . .
I3 I 0.79551(3) 0.55570(5) 0.14722(2) 0.01764(13) Uani 1 1 d U . .
I4 I 0.70354(3) -0.08345(6) 0.34629(2) 0.01952(13) Uani 1 1 d U . .
N1 N 0.9678(3) 0.2596(7) 0.1621(3) 0.0136(10) Uani 1 1 d U . .
N2 N 0.9825(3) 0.3047(7) 0.2996(3) 0.0145(11) Uani 1 1 d U . .
N3 N 0.9097(3) 0.2800(6) 0.2817(3) 0.0117(10) Uani 1 1 d U . .
N4 N 0.8862(3) 0.1893(7) 0.3235(3) 0.0144(10) Uani 1 1 d U . .
N5 N 0.5347(3) 0.2200(7) 0.3335(3) 0.0153(10) Uani 1 1 d U . .
N6 N 0.6135(3) 0.2799(7) 0.1694(3) 0.0157(11) Uani 1 1 d U . .
N7 N 0.5891(3) 0.1931(7) 0.2131(3) 0.0148(11) Uani 1 1 d U . .
N8 N 0.5166(3) 0.1733(7) 0.1965(3) 0.0151(11) Uani 1 1 d U . .
C1 C 0.9722(4) 0.1688(9) 0.1114(4) 0.0205(14) Uani 1 1 d U . .
H1 H 0.9282 0.1472 0.0840 0.025 Uiso 1 1 calc R . .
C2 C 1.0378(5) 0.1062(10) 0.0979(4) 0.0254(16) Uani 1 1 d U . .
H2 H 1.0387 0.0424 0.0621 0.031 Uiso 1 1 calc R . .
C3 C 1.1029(5) 0.1385(10) 0.1381(4) 0.0280(17) Uani 1 1 d U . .
H3 H 1.1488 0.0978 0.1297 0.034 Uiso 1 1 calc R . .
C4 C 1.0992(4) 0.2305(10) 0.1898(4) 0.0236(15) Uani 1 1 d U . .
H4 H 1.1426 0.2527 0.2178 0.028 Uiso 1 1 calc R . .
C5 C 1.0315(4) 0.2907(8) 0.2009(3) 0.0159(12) Uani 1 1 d U . .
C6 C 1.0241(4) 0.3879(8) 0.2572(3) 0.0156(13) Uani 1 1 d U . .
H6A H 1.0737 0.4141 0.2791 0.019 Uiso 1 1 calc R . .
H6B H 0.9984 0.4859 0.2439 0.019 Uiso 1 1 calc R . .
C7 C 1.0049(4) 0.2290(8) 0.3537(3) 0.0139(12) Uani 1 1 d U . .
H7 H 1.0532 0.2276 0.3764 0.017 Uiso 1 1 calc R . .
C8 C 0.9443(4) 0.1556(8) 0.3691(3) 0.0141(12) Uani 1 1 d U . .
C9 C 0.9351(4) 0.0544(9) 0.4245(3) 0.0188(15) Uani 1 1 d U . .
H9A H 0.9224 -0.0521 0.4098 0.023 Uiso 1 1 calc R . .
H9B H 0.8937 0.0943 0.4452 0.023 Uiso 1 1 calc R . .
C10 C 1.0045(4) 0.0499(8) 0.4716(3) 0.0161(14) Uani 1 1 d U . .
H10A H 1.0176 0.1568 0.4857 0.019 Uiso 1 1 calc R . .
H10B H 1.0456 0.0086 0.4510 0.019 Uiso 1 1 calc R . .
C11 C 0.5317(4) 0.3082(8) 0.3848(3) 0.0188(14) Uani 1 1 d U . .
H11 H 0.5766 0.3349 0.4101 0.023 Uiso 1 1 calc R . .
C12 C 0.4665(4) 0.3613(9) 0.4022(4) 0.0225(15) Uani 1 1 d U . .
H12 H 0.4666 0.4211 0.4392 0.027 Uiso 1 1 calc R . .
C13 C 0.4002(4) 0.3263(10) 0.3649(4) 0.0258(16) Uani 1 1 d U . .
H13 H 0.3547 0.3641 0.3754 0.031 Uiso 1 1 calc R . .
C14 C 0.4022(4) 0.2354(10) 0.3123(4) 0.0238(15) Uani 1 1 d U . .
H14 H 0.3577 0.2079 0.2865 0.029 Uiso 1 1 calc R . .
C15 C 0.4706(4) 0.1843(8) 0.2974(3) 0.0164(13) Uani 1 1 d U . .
C16 C 0.4758(4) 0.0891(8) 0.2396(3) 0.0174(13) Uani 1 1 d U . .
H16A H 0.5010 -0.0101 0.2516 0.021 Uiso 1 1 calc R . .
H16B H 0.4255 0.0651 0.2185 0.021 Uiso 1 1 calc R . .
C17 C 0.4939(4) 0.2456(8) 0.1424(3) 0.0175(13) Uani 1 1 d U . .
H17 H 0.4451 0.2491 0.1206 0.021 Uiso 1 1 calc R . .
C18 C 0.5559(4) 0.3139(9) 0.1249(3) 0.0185(14) Uani 1 1 d U . .
C19 C 0.5660(4) 0.4070(10) 0.0675(4) 0.0244(17) Uani 1 1 d U . .
H19A H 0.5959 0.3460 0.0413 0.029 Uiso 1 1 calc R . .
H19B H 0.5938 0.5026 0.0806 0.029 Uiso 1 1 calc R . .
C20 C 0.4936(4) 0.4512(8) 0.0284(3) 0.0155(14) Uani 1 1 d U . .
H20A H 0.4631 0.5107 0.0546 0.019 Uiso 1 1 calc R . .
H20B H 0.4663 0.3560 0.0139 0.019 Uiso 1 1 calc R . .
N1S N 0.8570(5) 0.3813(11) 0.4799(4) 0.055(2) Uani 1 1 d . . .
C2S C 0.7399(5) 0.2253(12) 0.4950(4) 0.036(2) Uani 1 1 d . . .
H2S1 H 0.7524 0.1554 0.5307 0.054 Uiso 1 1 calc R . .
H2S2 H 0.7230 0.1645 0.4574 0.054 Uiso 1 1 calc R . .
H2S3 H 0.7006 0.2961 0.5036 0.054 Uiso 1 1 calc R . .
C1S C 0.8014(6) 0.3096(12) 0.4856(4) 0.039(2) 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
N2S C3S 1.126(12) . ?
C3S C4S 1.494(14) . ?
N2X C1X 1.099(19) . ?
C1X C2X 1.50(2) . ?
Cu1 N1 2.076(6) . ?
Cu1 N3 2.085(6) . ?
Cu1 I3 2.5511(11) . ?
Cu1 Cu2 2.6409(13) . ?
Cu1 I1 2.6588(11) . ?
Cu2 N6 2.044(6) . ?
Cu2 I3 2.5911(11) . ?
Cu2 I1 2.7086(12) . ?
Cu2 I2 2.7665(12) . ?
Cu2 Cu3 2.9692(15) . ?
Cu3 N4 2.035(6) . ?
Cu3 I4 2.5836(11) . ?
Cu3 Cu4 2.6348(14) . ?
Cu3 I2 2.7141(12) . ?
Cu3 I1 2.8152(12) . ?
Cu4 N5 2.071(6) . ?
Cu4 N7 2.081(6) . ?
Cu4 I4 2.5525(11) . ?
Cu4 I2 2.6407(11) . ?
N1 C1 1.355(9) . ?
N1 C5 1.365(9) . ?
N2 C7 1.351(9) . ?
N2 N3 1.352(8) . ?
N2 C6 1.456(8) . ?
N3 N4 1.309(7) . ?
N4 C8 1.377(9) . ?
N5 C11 1.350(9) . ?
N5 C15 1.352(9) . ?
N6 N7 1.328(8) . ?
N6 C18 1.355(9) . ?
N7 N8 1.335(8) . ?
N8 C17 1.338(9) . ?
N8 C16 1.463(9) . ?
C1 C2 1.382(10) . ?
C2 C3 1.401(12) . ?
C3 C4 1.377(11) . ?
C4 C5 1.392(10) . ?
C5 C6 1.497(10) . ?
C7 C8 1.356(9) . ?
C8 C9 1.507(9) . ?
C9 C10 1.513(10) . ?
C10 C10 1.524(14) 3_756 ?
C11 C12 1.376(10) . ?
C12 C13 1.392(11) . ?
C13 C14 1.384(11) . ?
C14 C15 1.403(10) . ?
C15 C16 1.506(10) . ?
C17 C18 1.376(10) . ?
C18 C19 1.508(10) . ?
C19 C20 1.517(10) . ?
C20 C20 1.528(14) 3_665 ?
N1S C1S 1.211(12) . ?
C2S C1S 1.376(12) . ?

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
N2S C3S C4S 179.8(15) . . ?
N2X C1X C2X 167(8) . . ?
N1 Cu1 N3 89.3(2) . . ?
N1 Cu1 I3 121.01(16) . . ?
N3 Cu1 I3 123.74(16) . . ?
N1 Cu1 Cu2 164.01(17) . . ?
N3 Cu1 Cu2 103.16(15) . . ?
I3 Cu1 Cu2 59.85(3) . . ?
N1 Cu1 I1 107.45(16) . . ?
N3 Cu1 I1 97.78(16) . . ?
I3 Cu1 I1 113.23(4) . . ?
Cu2 Cu1 I1 61.47(3) . . ?
N6 Cu2 I3 127.88(17) . . ?
N6 Cu2 Cu1 155.37(18) . . ?
I3 Cu2 Cu1 58.36(3) . . ?
N6 Cu2 I1 99.31(17) . . ?
I3 Cu2 I1 110.34(4) . . ?
Cu1 Cu2 I1 59.59(3) . . ?
N6 Cu2 I2 98.07(17) . . ?
I3 Cu2 I2 105.77(4) . . ?
Cu1 Cu2 I2 102.59(4) . . ?
I1 Cu2 I2 115.58(3) . . ?
N6 Cu2 Cu3 105.76(17) . . ?
I3 Cu2 Cu3 126.11(4) . . ?
Cu1 Cu2 Cu3 75.57(3) . . ?
I1 Cu2 Cu3 59.24(3) . . ?
I2 Cu2 Cu3 56.35(3) . . ?
N4 Cu3 I4 128.59(17) . . ?
N4 Cu3 Cu4 154.33(17) . . ?
I4 Cu3 Cu4 58.56(3) . . ?
N4 Cu3 I2 98.80(17) . . ?
I4 Cu3 I2 110.82(4) . . ?
Cu4 Cu3 I2 59.14(3) . . ?
N4 Cu3 I1 97.31(16) . . ?
I4 Cu3 I1 107.04(4) . . ?
Cu4 Cu3 I1 103.57(4) . . ?
I2 Cu3 I1 113.81(3) . . ?
N4 Cu3 Cu2 105.50(17) . . ?
I4 Cu3 Cu2 125.71(4) . . ?
Cu4 Cu3 Cu2 75.19(3) . . ?
I2 Cu3 Cu2 58.05(3) . . ?
I1 Cu3 Cu2 55.76(3) . . ?
N5 Cu4 N7 89.2(2) . . ?
N5 Cu4 I4 120.89(16) . . ?
N7 Cu4 I4 123.29(17) . . ?
N5 Cu4 Cu3 163.48(17) . . ?
N7 Cu4 Cu3 104.08(15) . . ?
I4 Cu4 Cu3 59.72(3) . . ?
N5 Cu4 I2 107.12(17) . . ?
N7 Cu4 I2 97.55(16) . . ?
I4 Cu4 I2 114.26(4) . . ?
Cu3 Cu4 I2 61.92(3) . . ?
Cu1 I1 Cu2 58.94(3) . . ?
Cu1 I1 Cu3 78.00(3) . . ?
Cu2 I1 Cu3 65.00(3) . . ?
Cu4 I2 Cu3 58.93(3) . . ?
Cu4 I2 Cu2 78.68(3) . . ?
Cu3 I2 Cu2 65.60(3) . . ?
Cu1 I3 Cu2 61.80(3) . . ?
Cu4 I4 Cu3 61.72(3) . . ?
C1 N1 C5 117.9(6) . . ?
C1 N1 Cu1 120.0(5) . . ?
C5 N1 Cu1 121.0(5) . . ?
C7 N2 N3 109.9(5) . . ?
C7 N2 C6 131.2(6) . . ?
N3 N2 C6 118.5(5) . . ?
N4 N3 N2 107.5(5) . . ?
N4 N3 Cu1 128.8(4) . . ?
N2 N3 Cu1 119.4(4) . . ?
N3 N4 C8 108.9(5) . . ?
N3 N4 Cu3 112.0(4) . . ?
C8 N4 Cu3 139.0(5) . . ?
C11 N5 C15 118.2(6) . . ?
C11 N5 Cu4 120.5(5) . . ?
C15 N5 Cu4 121.0(5) . . ?
N7 N6 C18 108.6(6) . . ?
N7 N6 Cu2 111.5(4) . . ?
C18 N6 Cu2 139.5(5) . . ?
N6 N7 N8 107.4(5) . . ?
N6 N7 Cu4 128.5(4) . . ?
N8 N7 Cu4 120.0(4) . . ?
N7 N8 C17 110.7(6) . . ?
N7 N8 C16 117.9(6) . . ?
C17 N8 C16 131.3(6) . . ?
N1 C1 C2 122.9(7) . . ?
C1 C2 C3 118.7(8) . . ?
C4 C3 C2 118.9(7) . . ?
C3 C4 C5 119.8(8) . . ?
N1 C5 C4 121.7(7) . . ?
N1 C5 C6 116.3(6) . . ?
C4 C5 C6 122.0(7) . . ?
N2 C6 C5 110.2(6) . . ?
N2 C7 C8 106.1(6) . . ?
C7 C8 N4 107.6(6) . . ?
C7 C8 C9 130.4(6) . . ?
N4 C8 C9 122.0(6) . . ?
C8 C9 C10 111.8(6) . . ?
C9 C10 C10 112.4(7) . 3_756 ?
N5 C11 C12 123.0(7) . . ?
C11 C12 C13 119.2(7) . . ?
C14 C13 C12 118.6(7) . . ?
C13 C14 C15 119.3(7) . . ?
N5 C15 C14 121.7(7) . . ?
N5 C15 C16 117.0(6) . . ?
C14 C15 C16 121.3(7) . . ?
N8 C16 C15 110.5(6) . . ?
N8 C17 C18 105.5(6) . . ?
N6 C18 C17 107.7(6) . . ?
N6 C18 C19 121.7(6) . . ?
C17 C18 C19 130.5(7) . . ?
C18 C19 C20 113.3(6) . . ?
C19 C20 C20 111.5(7) . 3_665 ?
N1S C1S C2S 177.0(11) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         3.372
_refine_diff_density_min         -1.755
_refine_diff_density_rms         0.301
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2
_database_code_depnum_ccdc_archive 'CCDC 1000337'
_audit_update_record             
;
2014-11-17 deposited with the CCDC.
2015-03-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H14 Cu2 I2 N4'
_chemical_formula_weight         583.14

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'
I I -0.4742 1.8119 '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                   15.9272(8)
_cell_length_b                   9.0050(4)
_cell_length_c                   22.3483(11)
_cell_angle_alpha                90
_cell_angle_beta                 102.1050(10)
_cell_angle_gamma                90
_cell_volume                     3134.0(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    9815
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      33.22

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.472
_exptl_crystal_F_000             2176
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    6.645
_shelx_estimated_absorpt_T_min   0.232
_shelx_estimated_absorpt_T_max   0.879
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4645
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_process_details   'SADABS, (Sheldrick 2008)'


_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'APEX DUO'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            39341
_diffrn_reflns_av_unetI/netI     0.0167
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         1.864
_diffrn_reflns_theta_max         33.229
_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             5992
_reflns_number_gt                5453
_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 DUO'
_computing_cell_refinement       'Bruker DUO'
_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          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0101P)²+18.5059P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5992
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0322
_refine_ls_R_factor_gt           0.0276
_refine_ls_wR_factor_ref         0.0555
_refine_ls_wR_factor_gt          0.0541
_refine_ls_goodness_of_fit_ref   1.175
_refine_ls_restrained_S_all      1.175
_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 0.32646(2) 0.64039(4) 0.41025(2) 0.02781(8) Uani 1 1 d . . . . .
Cu2 Cu 0.26604(2) 0.87208(4) 0.46326(2) 0.02185(7) Uani 1 1 d . . . . .
I1 I 0.38906(2) 0.90027(2) 0.40435(2) 0.02480(4) Uani 1 1 d . . . . .
I2 I 0.15887(2) 0.65421(2) 0.41320(2) 0.01850(4) Uani 1 1 d . . . . .
N1 N 0.34995(15) 0.4823(3) 0.34742(11) 0.0225(5) Uani 1 1 d . . . . .
N2 N 0.40242(17) 0.3659(4) 0.47430(12) 0.0376(8) Uani 1 1 d . . . . .
N3 N 0.35858(15) 0.4902(3) 0.48046(11) 0.0263(5) Uani 1 1 d . . . . .
N4 N 0.31874(14) 0.4658(3) 0.52606(11) 0.0216(4) Uani 1 1 d . . . . .
C1 C 0.3074(2) 0.4895(4) 0.28930(14) 0.0285(6) Uani 1 1 d . . . . .
H1A H 0.2668 0.5672 0.2778 0.034 Uiso 1 1 calc R U . . .
C2 C 0.3193(2) 0.3896(4) 0.24507(14) 0.0340(7) Uani 1 1 d . . . . .
H2A H 0.2882 0.3994 0.2041 0.041 Uiso 1 1 calc R U . . .
C3 C 0.37710(19) 0.2752(3) 0.26126(13) 0.0251(5) Uani 1 1 d . . . . .
H3A H 0.3869 0.2053 0.2316 0.030 Uiso 1 1 calc R U . . .
C4 C 0.42043(17) 0.2643(3) 0.32135(13) 0.0229(5) Uani 1 1 d . . . . .
H4A H 0.4602 0.1860 0.3339 0.027 Uiso 1 1 calc R U . . .
C5 C 0.40526(17) 0.3691(4) 0.36328(13) 0.0255(6) Uani 1 1 d . . . . .
C6 C 0.4557(2) 0.3625(6) 0.42846(16) 0.0544(14) Uani 1 1 d . . . . .
H6A H 0.4904 0.2704 0.4339 0.065 Uiso 1 1 calc R U . . .
H6B H 0.4960 0.4476 0.4356 0.065 Uiso 1 1 calc R U . . .
C7 C 0.3929(2) 0.2642(5) 0.51575(15) 0.0453(11) Uani 1 1 d . . . . .
H7A H 0.4179 0.1680 0.5209 0.054 Uiso 1 1 calc R U . . .
C8 C 0.3389(2) 0.3277(4) 0.54969(14) 0.0304(7) Uani 1 1 d . . . . .
C9 C 0.3125(2) 0.2745(4) 0.60535(15) 0.0356(8) Uani 1 1 d . . . . .
H9A H 0.2859 0.1751 0.5974 0.043 Uiso 1 1 calc R U . . .
H9B H 0.2689 0.3428 0.6156 0.043 Uiso 1 1 calc R U . . .
C10 C 0.3898(3) 0.2648(5) 0.66046(18) 0.0493(10) Uani 1 1 d . . . . .
C11' C 0.4385(4) 0.3878(8) 0.6716(3) 0.0339(14) Uani 0.5 1 d . . P . .
H11A H 0.4446 0.4322 0.6327 0.051 Uiso 0.5 1 calc R U P . .
H11B H 0.4111 0.4592 0.6944 0.051 Uiso 0.5 1 calc R U P . .
H11C H 0.4954 0.3616 0.6956 0.051 Uiso 0.5 1 calc R U P . .
C11 C 0.3771(5) 0.1949(9) 0.7100(3) 0.0393(16) Uani 0.5 1 d . . P . .
H11D H 0.3412 0.1072 0.6979 0.059 Uiso 0.5 1 calc R U P . .
H11E H 0.4325 0.1642 0.7350 0.059 Uiso 0.5 1 calc R U P . .
H11F H 0.3482 0.2618 0.7338 0.059 Uiso 0.5 1 calc R U 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
Cu1 N3 2.053(3) . ?
Cu1 N1 2.087(2) . ?
Cu1 I1 2.5580(4) . ?
Cu1 Cu2 2.6760(5) . ?
Cu1 I2 2.6867(4) . ?
Cu2 N4 2.036(2) 7_566 ?
Cu2 I1 2.5921(4) . ?
Cu2 I2 2.6858(4) . ?
Cu2 I2 2.7791(4) 7_566 ?
Cu2 Cu2 2.8536(8) 7_566 ?
I2 Cu2 2.7792(4) 7_566 ?
N1 C1 1.335(4) . ?
N1 C5 1.345(4) . ?
N2 C7 1.334(6) . ?
N2 N3 1.342(3) . ?
N2 C6 1.462(5) . ?
N3 N4 1.327(3) . ?
N4 C8 1.363(4) . ?
N4 Cu2 2.036(2) 7_566 ?
C1 C2 1.379(4) . ?
C2 C3 1.378(5) . ?
C3 C4 1.378(4) . ?
C4 C5 1.387(4) . ?
C5 C6 1.510(4) . ?
C7 C8 1.384(4) . ?
C8 C9 1.474(5) . ?
C9 C10 1.550(5) . ?
C10 C11 1.326(8) . ?
C10 C11' 1.345(8) . ?

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 N1 90.80(10) . . ?
N3 Cu1 I1 127.20(7) . . ?
N1 Cu1 I1 117.53(7) . . ?
N3 Cu1 Cu2 103.31(6) . . ?
N1 Cu1 Cu2 163.99(7) . . ?
I1 Cu1 Cu2 59.320(12) . . ?
N3 Cu1 I2 95.82(7) . . ?
N1 Cu1 I2 111.55(6) . . ?
I1 Cu1 I2 111.030(15) . . ?
Cu2 Cu1 I2 60.110(11) . . ?
N4 Cu2 I1 125.44(8) 7_566 . ?
N4 Cu2 Cu1 156.88(7) 7_566 . ?
I1 Cu2 Cu1 58.074(12) . . ?
N4 Cu2 I2 101.14(7) 7_566 . ?
I1 Cu2 I2 109.999(13) . . ?
Cu1 Cu2 I2 60.143(12) . . ?
N4 Cu2 I2 95.88(7) 7_566 7_566 ?
I1 Cu2 I2 107.413(13) . 7_566 ?
Cu1 Cu2 I2 104.690(15) . 7_566 ?
I2 Cu2 I2 117.072(14) . 7_566 ?
N4 Cu2 Cu2 106.37(8) 7_566 7_566 ?
I1 Cu2 Cu2 127.832(19) . 7_566 ?
Cu1 Cu2 Cu2 77.198(17) . 7_566 ?
I2 Cu2 Cu2 60.136(13) . 7_566 ?
I2 Cu2 Cu2 56.937(13) 7_566 7_566 ?
Cu1 I1 Cu2 62.606(12) . . ?
Cu2 I2 Cu1 59.747(11) . . ?
Cu2 I2 Cu2 62.927(14) . 7_566 ?
Cu1 I2 Cu2 78.323(12) . 7_566 ?
C1 N1 C5 117.6(2) . . ?
C1 N1 Cu1 119.7(2) . . ?
C5 N1 Cu1 122.64(19) . . ?
C7 N2 N3 111.4(3) . . ?
C7 N2 C6 129.8(3) . . ?
N3 N2 C6 118.7(4) . . ?
N4 N3 N2 106.5(3) . . ?
N4 N3 Cu1 127.83(18) . . ?
N2 N3 Cu1 121.5(2) . . ?
N3 N4 C8 109.7(2) . . ?
N3 N4 Cu2 114.01(19) . 7_566 ?
C8 N4 Cu2 135.8(2) . 7_566 ?
N1 C1 C2 123.2(3) . . ?
C3 C2 C1 119.0(3) . . ?
C2 C3 C4 118.7(3) . . ?
C3 C4 C5 119.2(3) . . ?
N1 C5 C4 122.4(3) . . ?
N1 C5 C6 118.1(3) . . ?
C4 C5 C6 119.5(3) . . ?
N2 C6 C5 113.9(2) . . ?
N2 C7 C8 105.7(3) . . ?
N4 C8 C7 106.7(3) . . ?
N4 C8 C9 122.6(3) . . ?
C7 C8 C9 130.3(3) . . ?
C8 C9 C10 111.7(3) . . ?
C11 C10 C11' 114.8(5) . . ?
C11 C10 C9 117.1(5) . . ?
C11' C10 C9 115.5(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N2 N3 N4 -1.3(3) . . . . ?
C6 N2 N3 N4 -177.7(3) . . . . ?
C7 N2 N3 Cu1 -160.0(2) . . . . ?
C6 N2 N3 Cu1 23.6(4) . . . . ?
N2 N3 N4 C8 1.4(3) . . . . ?
Cu1 N3 N4 C8 158.3(2) . . . . ?
N2 N3 N4 Cu2 -171.78(17) . . . 7_566 ?
Cu1 N3 N4 Cu2 -14.9(3) . . . 7_566 ?
C5 N1 C1 C2 -1.9(5) . . . . ?
Cu1 N1 C1 C2 179.9(3) . . . . ?
N1 C1 C2 C3 0.8(5) . . . . ?
C1 C2 C3 C4 0.5(5) . . . . ?
C2 C3 C4 C5 -0.6(5) . . . . ?
C1 N1 C5 C4 1.7(4) . . . . ?
Cu1 N1 C5 C4 179.9(2) . . . . ?
C1 N1 C5 C6 178.2(3) . . . . ?
Cu1 N1 C5 C6 -3.7(4) . . . . ?
C3 C4 C5 N1 -0.5(5) . . . . ?
C3 C4 C5 C6 -176.9(3) . . . . ?
C7 N2 C6 C5 117.3(4) . . . . ?
N3 N2 C6 C5 -67.1(5) . . . . ?
N1 C5 C6 N2 54.7(5) . . . . ?
C4 C5 C6 N2 -128.7(4) . . . . ?
N3 N2 C7 C8 0.7(4) . . . . ?
C6 N2 C7 C8 176.5(3) . . . . ?
N3 N4 C8 C7 -1.0(3) . . . . ?
Cu2 N4 C8 C7 170.1(2) 7_566 . . . ?
N3 N4 C8 C9 172.9(3) . . . . ?
Cu2 N4 C8 C9 -16.1(5) 7_566 . . . ?
N2 C7 C8 N4 0.2(4) . . . . ?
N2 C7 C8 C9 -173.0(3) . . . . ?
N4 C8 C9 C10 -108.1(3) . . . . ?
C7 C8 C9 C10 64.2(5) . . . . ?
C8 C9 C10 C11 -168.9(5) . . . . ?
C8 C9 C10 C11' 51.0(6) . . . . ?

_refine_diff_density_max         1.243
_refine_diff_density_min         -1.483
_refine_diff_density_rms         0.132

#===end
####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 1034399'
_audit_update_record             
;
2015-01-07 deposited with the CCDC.
2015-03-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H14 Cl2 N4 Zn'
_chemical_formula_weight         338.53

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'
Zn Zn 0.2839 1.4301 '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                   7.1708(4)
_cell_length_b                   8.4435(4)
_cell_length_c                   12.2732(6)
_cell_angle_alpha                91.2260(11)
_cell_angle_beta                 101.3998(12)
_cell_angle_gamma                111.3897(10)
_cell_volume                     674.70(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9293
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      28.29

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.666
_exptl_crystal_F_000             344
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    2.202
_shelx_estimated_absorpt_T_min   0.473
_shelx_estimated_absorpt_T_max   0.844
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4752
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS, (Sheldrick 2008)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'APEX DUO'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24861
_diffrn_reflns_av_unetI/netI     0.0141
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.702
_diffrn_reflns_theta_max         28.303
_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             3368
_reflns_number_gt                3291
_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 DUO'
_computing_cell_refinement       'Bruker DUO'
_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          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0148P)²+0.5309P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3368
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0186
_refine_ls_R_factor_gt           0.0181
_refine_ls_wR_factor_ref         0.0444
_refine_ls_wR_factor_gt          0.0442
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_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
Zn1 Zn 0.53510(2) -0.19730(2) 0.76510(2) 0.00988(4) Uani 1 1 d . . . . .
Cl1 Cl 0.37329(5) -0.16349(4) 0.59852(3) 0.02054(7) Uani 1 1 d . . . . .
Cl2 Cl 0.34901(5) -0.24487(4) 0.89548(3) 0.01570(7) Uani 1 1 d . . . . .
N1 N 0.80904(16) 0.01351(13) 0.82312(9) 0.00987(19) Uani 1 1 d . . . . .
N2 N 0.66149(16) 0.37213(13) 0.75588(9) 0.0123(2) Uani 1 1 d . . . . .
N3 N 0.59909(16) 0.48223(13) 0.80194(9) 0.0118(2) Uani 1 1 d . . . . .
N4 N 0.64863(16) 0.61742(13) 0.74500(9) 0.01092(19) Uani 1 1 d . . . . .
C1 C 0.98137(19) -0.01793(16) 0.85844(10) 0.0115(2) Uani 1 1 d . . . . .
H1A H 0.9744 -0.1319 0.8475 0.014 Uiso 1 1 calc R U . . .
C2 C 1.16729(19) 0.10722(17) 0.90970(10) 0.0136(2) Uani 1 1 d . . . . .
H2A H 1.2850 0.0796 0.9340 0.016 Uiso 1 1 calc R U . . .
C3 C 1.1792(2) 0.27408(17) 0.92513(11) 0.0151(2) Uani 1 1 d . . . . .
H3A H 1.3051 0.3629 0.9604 0.018 Uiso 1 1 calc R U . . .
C4 C 1.0040(2) 0.30881(16) 0.88808(11) 0.0147(2) Uani 1 1 d . . . . .
H4A H 1.0086 0.4223 0.8972 0.018 Uiso 1 1 calc R U . . .
C5 C 0.82165(19) 0.17625(15) 0.83748(10) 0.0110(2) Uani 1 1 d . . . . .
C6 C 0.6250(2) 0.20590(15) 0.79903(12) 0.0152(2) Uani 1 1 d . . . . .
H6A H 0.5314 0.1145 0.7398 0.018 Uiso 1 1 calc R U . . .
H6B H 0.5568 0.1994 0.8624 0.018 Uiso 1 1 calc R U . . .
C7 C 0.7505(2) 0.43369(16) 0.67028(11) 0.0151(2) Uani 1 1 d . . . . .
H7A H 0.8055 0.3782 0.6245 0.018 Uiso 1 1 calc R U . . .
C8 C 0.74406(19) 0.59387(16) 0.66380(11) 0.0127(2) Uani 1 1 d . . . . .
C9 C 0.8225(2) 0.72704(16) 0.58818(11) 0.0165(3) Uani 1 1 d . . . . .
H9A H 0.9675 0.7992 0.6220 0.020 Uiso 1 1 calc R U . . .
H9B H 0.7424 0.8015 0.5818 0.020 Uiso 1 1 calc R U . . .
C10 C 0.8095(2) 0.65229(18) 0.47196(11) 0.0183(3) Uani 1 1 d . . . . .
H10A H 0.6658 0.5759 0.4391 0.022 Uiso 1 1 calc R U . . .
H10B H 0.8956 0.5828 0.4775 0.022 Uiso 1 1 calc R U . . .
C11 C 0.8807(2) 0.79111(19) 0.39548(12) 0.0217(3) Uani 1 1 d . . . . .
H11A H 0.8701 0.7382 0.3215 0.032 Uiso 1 1 calc R U . . .
H11B H 0.7941 0.8588 0.3887 0.032 Uiso 1 1 calc R U . . .
H11C H 1.0238 0.8657 0.4270 0.032 Uiso 1 1 calc R 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
Zn1 N4 2.0403(10) 1_545 ?
Zn1 N1 2.0920(10) . ?
Zn1 Cl1 2.2218(4) . ?
Zn1 Cl2 2.2324(3) . ?
N1 C1 1.3483(16) . ?
N1 C5 1.3491(15) . ?
N2 N3 1.3286(14) . ?
N2 C7 1.3518(17) . ?
N2 C6 1.4620(15) . ?
N3 N4 1.3244(14) . ?
N4 C8 1.3644(16) . ?
N4 Zn1 2.0403(10) 1_565 ?
C1 C2 1.3792(18) . ?
C2 C3 1.3865(18) . ?
C3 C4 1.3856(19) . ?
C4 C5 1.3894(17) . ?
C5 C6 1.5079(17) . ?
C7 C8 1.3733(17) . ?
C8 C9 1.4939(17) . ?
C9 C10 1.5190(18) . ?
C10 C11 1.5217(19) . ?

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
N4 Zn1 N1 100.18(4) 1_545 . ?
N4 Zn1 Cl1 108.36(3) 1_545 . ?
N1 Zn1 Cl1 110.76(3) . . ?
N4 Zn1 Cl2 112.81(3) 1_545 . ?
N1 Zn1 Cl2 109.14(3) . . ?
Cl1 Zn1 Cl2 114.650(14) . . ?
C1 N1 C5 117.85(11) . . ?
C1 N1 Zn1 117.37(8) . . ?
C5 N1 Zn1 124.46(8) . . ?
N3 N2 C7 112.16(10) . . ?
N3 N2 C6 119.15(10) . . ?
C7 N2 C6 128.69(11) . . ?
N4 N3 N2 105.54(10) . . ?
N3 N4 C8 110.72(10) . . ?
N3 N4 Zn1 119.92(8) . 1_565 ?
C8 N4 Zn1 128.24(8) . 1_565 ?
N1 C1 C2 123.21(11) . . ?
C1 C2 C3 118.77(12) . . ?
C4 C3 C2 118.72(12) . . ?
C3 C4 C5 119.42(12) . . ?
N1 C5 C4 122.03(12) . . ?
N1 C5 C6 116.33(11) . . ?
C4 C5 C6 121.61(11) . . ?
N2 C6 C5 111.95(10) . . ?
N2 C7 C8 105.08(11) . . ?
N4 C8 C7 106.49(11) . . ?
N4 C8 C9 122.76(11) . . ?
C7 C8 C9 130.75(12) . . ?
C8 C9 C10 113.16(11) . . ?
C9 C10 C11 111.81(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
C7 N2 N3 N4 0.02(14) . . . . ?
C6 N2 N3 N4 -178.78(11) . . . . ?
N2 N3 N4 C8 -0.62(14) . . . . ?
N2 N3 N4 Zn1 168.26(8) . . . 1_565 ?
C5 N1 C1 C2 1.07(18) . . . . ?
Zn1 N1 C1 C2 -172.76(9) . . . . ?
N1 C1 C2 C3 -0.56(19) . . . . ?
C1 C2 C3 C4 -0.23(19) . . . . ?
C2 C3 C4 C5 0.46(19) . . . . ?
C1 N1 C5 C4 -0.81(18) . . . . ?
Zn1 N1 C5 C4 172.55(9) . . . . ?
C1 N1 C5 C6 -178.84(11) . . . . ?
Zn1 N1 C5 C6 -5.48(15) . . . . ?
C3 C4 C5 N1 0.06(19) . . . . ?
C3 C4 C5 C6 177.99(12) . . . . ?
N3 N2 C6 C5 -122.56(12) . . . . ?
C7 N2 C6 C5 58.86(18) . . . . ?
N1 C5 C6 N2 -146.36(11) . . . . ?
C4 C5 C6 N2 35.60(17) . . . . ?
N3 N2 C7 C8 0.57(15) . . . . ?
C6 N2 C7 C8 179.23(12) . . . . ?
N3 N4 C8 C7 0.98(15) . . . . ?
Zn1 N4 C8 C7 -166.74(9) 1_565 . . . ?
N3 N4 C8 C9 -178.34(12) . . . . ?
Zn1 N4 C8 C9 13.94(18) 1_565 . . . ?
N2 C7 C8 N4 -0.90(14) . . . . ?
N2 C7 C8 C9 178.34(13) . . . . ?
N4 C8 C9 C10 -147.24(13) . . . . ?
C7 C8 C9 C10 33.6(2) . . . . ?
C8 C9 C10 C11 177.20(12) . . . . ?

_refine_diff_density_max         0.396
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.056

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 1034401'
_audit_update_record             
;
2014-11-15 deposited with the CCDC.
2015-03-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H22 Cl2 N8 Zn'
_chemical_formula_weight         510.72

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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   9.0863(3)
_cell_length_b                   9.2004(4)
_cell_length_c                   14.2638(6)
_cell_angle_alpha                102.2560(10)
_cell_angle_beta                 94.3340(10)
_cell_angle_gamma                100.7420(10)
_cell_volume                     1136.56(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9934
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      27.75

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.492
_exptl_crystal_F_000             524
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.340
_shelx_estimated_absorpt_T_min   0.775
_shelx_estimated_absorpt_T_max   0.878
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6470
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS, (Sheldrick 2008)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'APEX DUO'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            40402
_diffrn_reflns_av_unetI/netI     0.0180
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.472
_diffrn_reflns_theta_max         27.889
_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             5417
_reflns_number_gt                4689
_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 DUO'
_computing_cell_refinement       'Bruker DUO'
_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          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0361P)²+0.2637P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5417
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0329
_refine_ls_R_factor_gt           0.0261
_refine_ls_wR_factor_ref         0.0690
_refine_ls_wR_factor_gt          0.0659
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_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
Zn1 Zn 0.60946(2) 0.81130(2) 0.75145(2) 0.03069(6) Uani 1 1 d . . . . .
Cl1 Cl 0.77739(5) 0.86866(5) 0.88382(3) 0.04464(11) Uani 1 1 d . . . . .
Cl2 Cl 0.64987(5) 0.96536(5) 0.65089(3) 0.04360(11) Uani 1 1 d . . . . .
N1 N 0.13904(17) 0.51429(18) 0.90931(12) 0.0474(4) Uani 1 1 d . . . . .
N2 N 0.17053(14) 0.72897(15) 0.80013(11) 0.0378(3) Uani 1 1 d . . . . .
N3 N 0.28952(14) 0.69450(15) 0.75948(10) 0.0360(3) Uani 1 1 d . . . . .
N4 N 0.39946(14) 0.81559(14) 0.79160(10) 0.0322(3) Uani 1 1 d . . . . .
N5 N 0.92336(19) 1.3661(2) 0.56032(14) 0.0581(4) Uani 1 1 d . . . . .
N6 N 0.62924(15) 1.40498(15) 0.58123(10) 0.0354(3) Uani 1 1 d . . . . .
N7 N 0.63757(15) 1.55342(15) 0.60080(10) 0.0366(3) Uani 1 1 d . . . . .
N8 N 0.59791(14) 1.58815(14) 0.68841(10) 0.0325(3) Uani 1 1 d . . . . .
C1 C 0.1406(2) 0.4002(2) 0.95354(15) 0.0525(5) Uani 1 1 d . . . . .
H1A H 0.2088 0.4175 1.0087 0.063 Uiso 1 1 calc R U . . .
C2 C 0.0480(2) 0.2595(2) 0.92262(15) 0.0522(5) Uani 1 1 d . . . . .
H2A H 0.0521 0.1841 0.9565 0.063 Uiso 1 1 calc R U . . .
C3 C -0.0499(2) 0.2328(2) 0.84134(17) 0.0592(5) Uani 1 1 d . . . . .
H3A H -0.1133 0.1380 0.8178 0.071 Uiso 1 1 calc R U . . .
C4 C -0.0541(2) 0.3475(2) 0.79426(16) 0.0520(5) Uani 1 1 d . . . . .
H4A H -0.1203 0.3315 0.7383 0.062 Uiso 1 1 calc R U . . .
C5 C 0.04068(17) 0.48668(19) 0.83086(13) 0.0379(4) Uani 1 1 d . . . . .
C6 C 0.02920(18) 0.6155(2) 0.78228(15) 0.0450(4) Uani 1 1 d . . . . .
H6A H 0.0034 0.5750 0.7132 0.054 Uiso 1 1 calc R U . . .
H6B H -0.0511 0.6640 0.8061 0.054 Uiso 1 1 calc R U . . .
C7 C 0.20134(19) 0.86925(18) 0.85718(14) 0.0418(4) Uani 1 1 d . . . . .
H7A H 0.1356 0.9176 0.8930 0.050 Uiso 1 1 calc R U . . .
C8 C 0.34967(18) 0.92672(17) 0.85176(12) 0.0340(3) Uani 1 1 d . . . . .
C9 C 0.4455(2) 1.07976(17) 0.89393(12) 0.0387(4) Uani 1 1 d . . . . .
H9A H 0.5502 1.0710 0.9019 0.046 Uiso 1 1 calc R U . . .
H9B H 0.4178 1.1187 0.9574 0.046 Uiso 1 1 calc R U . . .
C10 C 0.42939(19) 1.19231(17) 0.83080(13) 0.0386(4) Uani 1 1 d . . . . .
H10A H 0.4499 1.1504 0.7659 0.046 Uiso 1 1 calc R U . . .
H10B H 0.3266 1.2077 0.8269 0.046 Uiso 1 1 calc R U . . .
C11 C 0.5372(2) 1.34402(18) 0.87155(13) 0.0408(4) Uani 1 1 d . . . . .
H11A H 0.6396 1.3296 0.8661 0.049 Uiso 1 1 calc R U . . .
H11B H 0.5278 1.3759 0.9398 0.049 Uiso 1 1 calc R U . . .
C12 C 0.5130(2) 1.47129(19) 0.82296(13) 0.0447(4) Uani 1 1 d . . . . .
H12A H 0.4063 1.4727 0.8176 0.054 Uiso 1 1 calc R U . . .
H12B H 0.5657 1.5672 0.8649 0.054 Uiso 1 1 calc R U . . .
C13 C 0.56386(17) 1.46224(17) 0.72461(12) 0.0337(3) Uani 1 1 d . . . . .
C14 C 0.58504(19) 1.34369(18) 0.65432(13) 0.0388(4) Uani 1 1 d . . . . .
H14A H 0.5716 1.2419 0.6568 0.047 Uiso 1 1 calc R U . . .
C15 C 0.6645(2) 1.3282(2) 0.48749(13) 0.0468(4) Uani 1 1 d . . . . .
H15A H 0.6629 1.3949 0.4433 0.056 Uiso 1 1 calc R U . . .
H15B H 0.5867 1.2376 0.4616 0.056 Uiso 1 1 calc R U . . .
C16 C 0.8161(2) 1.2834(2) 0.49241(13) 0.0457(4) Uani 1 1 d . . . . .
C17 C 0.8392(3) 1.1632(3) 0.42216(17) 0.0697(7) Uani 1 1 d . . . . .
H17A H 0.7608 1.1047 0.3761 0.084 Uiso 1 1 calc R U . . .
C18 C 0.9840(4) 1.1330(3) 0.4229(2) 0.0866(9) Uani 1 1 d . . . . .
H18A H 1.0047 1.0548 0.3760 0.104 Uiso 1 1 calc R U . . .
C19 C 1.0950(3) 1.2189(4) 0.4930(2) 0.0849(9) Uani 1 1 d . . . . .
H19A H 1.1923 1.2006 0.4950 0.102 Uiso 1 1 calc R U . . .
C20 C 1.0602(3) 1.3316(3) 0.5597(2) 0.0758(7) Uani 1 1 d . . . . .
H20A H 1.1359 1.3886 0.6081 0.091 Uiso 1 1 calc R 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
Zn1 N4 2.0382(12) . ?
Zn1 N8 2.0387(12) 1_545 ?
Zn1 Cl2 2.2248(4) . ?
Zn1 Cl1 2.2390(5) . ?
N1 C5 1.326(2) . ?
N1 C1 1.336(3) . ?
N2 N3 1.3230(18) . ?
N2 C7 1.338(2) . ?
N2 C6 1.463(2) . ?
N3 N4 1.3222(18) . ?
N4 C8 1.3583(19) . ?
N5 C16 1.317(3) . ?
N5 C20 1.340(3) . ?
N6 N7 1.3210(18) . ?
N6 C14 1.340(2) . ?
N6 C15 1.462(2) . ?
N7 N8 1.3172(18) . ?
N8 C13 1.3597(19) . ?
N8 Zn1 2.0387(12) 1_565 ?
C1 C2 1.369(3) . ?
C2 C3 1.355(3) . ?
C3 C4 1.371(3) . ?
C4 C5 1.375(2) . ?
C5 C6 1.510(2) . ?
C7 C8 1.367(2) . ?
C8 C9 1.486(2) . ?
C9 C10 1.529(2) . ?
C10 C11 1.518(2) . ?
C11 C12 1.522(2) . ?
C12 C13 1.500(2) . ?
C13 C14 1.369(2) . ?
C15 C16 1.510(3) . ?
C16 C17 1.385(3) . ?
C17 C18 1.395(4) . ?
C18 C19 1.363(4) . ?
C19 C20 1.353(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N4 Zn1 N8 103.83(5) . 1_545 ?
N4 Zn1 Cl2 107.29(4) . . ?
N8 Zn1 Cl2 113.82(4) 1_545 . ?
N4 Zn1 Cl1 109.28(4) . . ?
N8 Zn1 Cl1 106.61(4) 1_545 . ?
Cl2 Zn1 Cl1 115.360(18) . . ?
C5 N1 C1 116.76(16) . . ?
N3 N2 C7 111.97(13) . . ?
N3 N2 C6 119.60(14) . . ?
C7 N2 C6 128.39(14) . . ?
N4 N3 N2 105.59(12) . . ?
N3 N4 C8 110.61(12) . . ?
N3 N4 Zn1 119.51(9) . . ?
C8 N4 Zn1 129.85(11) . . ?
C16 N5 C20 117.7(2) . . ?
N7 N6 C14 112.10(13) . . ?
N7 N6 C15 119.65(14) . . ?
C14 N6 C15 128.25(14) . . ?
N8 N7 N6 105.48(12) . . ?
N7 N8 C13 111.04(12) . . ?
N7 N8 Zn1 118.53(10) . 1_565 ?
C13 N8 Zn1 130.29(11) . 1_565 ?
N1 C1 C2 124.01(19) . . ?
C3 C2 C1 118.28(19) . . ?
C2 C3 C4 119.11(18) . . ?
C3 C4 C5 119.13(18) . . ?
N1 C5 C4 122.69(17) . . ?
N1 C5 C6 118.28(15) . . ?
C4 C5 C6 119.00(16) . . ?
N2 C6 C5 111.85(14) . . ?
N2 C7 C8 105.65(14) . . ?
N4 C8 C7 106.18(14) . . ?
N4 C8 C9 122.75(14) . . ?
C7 C8 C9 130.96(14) . . ?
C8 C9 C10 112.31(15) . . ?
C11 C10 C9 111.21(15) . . ?
C10 C11 C12 115.13(16) . . ?
C13 C12 C11 116.14(14) . . ?
N8 C13 C14 105.80(14) . . ?
N8 C13 C12 121.39(13) . . ?
C14 C13 C12 132.80(14) . . ?
N6 C14 C13 105.59(14) . . ?
N6 C15 C16 113.36(15) . . ?
N5 C16 C17 122.8(2) . . ?
N5 C16 C15 118.34(16) . . ?
C17 C16 C15 118.7(2) . . ?
C16 C17 C18 117.7(3) . . ?
C19 C18 C17 119.4(2) . . ?
C20 C19 C18 118.4(2) . . ?
N5 C20 C19 124.0(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N2 N3 N4 0.23(19) . . . . ?
C6 N2 N3 N4 -177.67(14) . . . . ?
N2 N3 N4 C8 -0.51(18) . . . . ?
N2 N3 N4 Zn1 177.69(10) . . . . ?
C14 N6 N7 N8 0.02(18) . . . . ?
C15 N6 N7 N8 179.12(14) . . . . ?
N6 N7 N8 C13 -0.19(17) . . . . ?
N6 N7 N8 Zn1 175.76(9) . . . 1_565 ?
C5 N1 C1 C2 0.0(3) . . . . ?
N1 C1 C2 C3 1.1(3) . . . . ?
C1 C2 C3 C4 -1.0(3) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C1 N1 C5 C4 -1.3(3) . . . . ?
C1 N1 C5 C6 176.46(17) . . . . ?
C3 C4 C5 N1 1.4(3) . . . . ?
C3 C4 C5 C6 -176.36(19) . . . . ?
N3 N2 C6 C5 70.1(2) . . . . ?
C7 N2 C6 C5 -107.4(2) . . . . ?
N1 C5 C6 N2 26.7(2) . . . . ?
C4 C5 C6 N2 -155.49(17) . . . . ?
N3 N2 C7 C8 0.1(2) . . . . ?
C6 N2 C7 C8 177.80(17) . . . . ?
N3 N4 C8 C7 0.59(19) . . . . ?
Zn1 N4 C8 C7 -177.36(12) . . . . ?
N3 N4 C8 C9 -175.92(14) . . . . ?
Zn1 N4 C8 C9 6.1(2) . . . . ?
N2 C7 C8 N4 -0.43(19) . . . . ?
N2 C7 C8 C9 175.69(17) . . . . ?
N4 C8 C9 C10 90.95(19) . . . . ?
C7 C8 C9 C10 -84.6(2) . . . . ?
C8 C9 C10 C11 -175.65(13) . . . . ?
C9 C10 C11 C12 -170.86(14) . . . . ?
C10 C11 C12 C13 -74.3(2) . . . . ?
N7 N8 C13 C14 0.28(18) . . . . ?
Zn1 N8 C13 C14 -175.05(11) 1_565 . . . ?
N7 N8 C13 C12 -179.05(15) . . . . ?
Zn1 N8 C13 C12 5.6(2) 1_565 . . . ?
C11 C12 C13 N8 -156.78(15) . . . . ?
C11 C12 C13 C14 24.1(3) . . . . ?
N7 N6 C14 C13 0.14(19) . . . . ?
C15 N6 C14 C13 -178.85(16) . . . . ?
N8 C13 C14 N6 -0.25(18) . . . . ?
C12 C13 C14 N6 178.97(18) . . . . ?
N7 N6 C15 C16 105.19(18) . . . . ?
C14 N6 C15 C16 -75.9(2) . . . . ?
C20 N5 C16 C17 0.6(3) . . . . ?
C20 N5 C16 C15 -175.5(2) . . . . ?
N6 C15 C16 N5 -28.8(3) . . . . ?
N6 C15 C16 C17 154.98(19) . . . . ?
N5 C16 C17 C18 -1.9(3) . . . . ?
C15 C16 C17 C18 174.2(2) . . . . ?
C16 C17 C18 C19 1.6(4) . . . . ?
C17 C18 C19 C20 -0.1(4) . . . . ?
C16 N5 C20 C19 1.0(4) . . . . ?
C18 C19 C20 N5 -1.2(4) . . . . ?

_refine_diff_density_max         0.415
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.046
