# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_compd1

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H16 N10 Ni'
_chemical_formula_sum            'C12 H16 N10 Ni'
_chemical_formula_weight         359.06

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'
Ni Ni 0.3393 1.1124 '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                   8.6717(2)
_cell_length_b                   9.0238(2)
_cell_length_c                   9.3952(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.504(3)
_cell_angle_gamma                90
_cell_volume                     732.91(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1795
_cell_measurement_theta_min      3.1090
_cell_measurement_theta_max      32.2550

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.627
_exptl_crystal_F_000             372
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    1.341
_shelx_estimated_absorpt_T_min   0.651
_shelx_estimated_absorpt_T_max   0.730
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.90372
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.0938
_diffrn_reflns_number            3075
_diffrn_reflns_av_unetI/netI     0.0225
_diffrn_reflns_av_R_equivalents  0.0158
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.356
_diffrn_reflns_theta_max         26.361
_diffrn_reflns_theta_full        25.000
_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             1488
_reflns_number_gt                1325
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ORTEP-III
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0265P)²+0.2719P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     DIRECT
_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         1488
_refine_ls_number_parameters     106
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0270
_refine_ls_R_factor_gt           0.0226
_refine_ls_wR_factor_ref         0.0584
_refine_ls_wR_factor_gt          0.0561
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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
Ni1 Ni 0.5000 0.0000 0.5000 0.01968(10) Uani 1 2 d S . P . .
N1 N 0.72607(15) 0.04238(15) 0.58193(14) 0.0215(3) Uani 1 1 d . . . . .
N2 N 0.58529(16) 0.10128(15) 0.32345(15) 0.0254(3) Uani 1 1 d . . . . .
H2A H 0.6201 0.0331 0.2655 0.030 Uiso 1 1 calc R U . . .
H2B H 0.5105 0.1524 0.2753 0.030 Uiso 1 1 calc R U . . .
N3 N 0.42583(18) 0.21187(16) 0.57787(16) 0.0307(3) Uani 1 1 d . . . . .
N4 N 0.36223(16) 0.30232(16) 0.50355(15) 0.0281(3) Uani 1 1 d . . . . .
N5 N 0.2979(2) 0.3931(2) 0.4342(2) 0.0560(5) Uani 1 1 d . . . . .
C1 C 0.80072(19) 0.14045(17) 0.50510(18) 0.0237(3) Uani 1 1 d . . . . .
C2 C 0.95168(19) 0.18394(18) 0.54423(19) 0.0288(4) Uani 1 1 d . . . . .
H2 H 1.0008 0.2527 0.4895 0.035 Uiso 1 1 calc R U . . .
C3 C 1.0276(2) 0.12432(19) 0.6646(2) 0.0310(4) Uani 1 1 d . . . . .
H3 H 1.1286 0.1525 0.6927 0.037 Uiso 1 1 calc R U . . .
C4 C 0.9521(2) 0.02210(18) 0.7434(2) 0.0302(4) Uani 1 1 d . . . . .
H4 H 1.0015 -0.0200 0.8251 0.036 Uiso 1 1 calc R U . . .
C5 C 0.8020(2) -0.01648(17) 0.69866(18) 0.0263(4) Uani 1 1 d . . . . .
H5 H 0.7515 -0.0860 0.7514 0.032 Uiso 1 1 calc R U . . .
C6 C 0.7120(2) 0.20130(19) 0.37464(19) 0.0296(4) Uani 1 1 d . . . . .
H6A H 0.6696 0.2973 0.3967 0.035 Uiso 1 1 calc R U . . .
H6B H 0.7816 0.2150 0.2997 0.035 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
Ni1 N2 2.0800(13) . Y
Ni1 N2 2.0800(13) 3_656 Y
Ni1 N1 2.0845(13) . Y
Ni1 N1 2.0845(13) 3_656 Y
Ni1 N3 2.1629(14) . Y
Ni1 N3 2.1629(14) 3_656 Y
N1 C1 1.340(2) . ?
N1 C5 1.344(2) . ?
N2 C6 1.473(2) . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
N3 N4 1.182(2) . ?
N4 N5 1.162(2) . ?
C1 C2 1.388(2) . ?
C1 C6 1.499(2) . ?
C2 C3 1.373(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.379(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(2) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Ni1 N2 180.00(7) . 3_656 Y
N2 Ni1 N1 80.26(5) . . Y
N2 Ni1 N1 99.74(5) 3_656 . Y
N2 Ni1 N1 99.74(5) . 3_656 Y
N2 Ni1 N1 80.26(5) 3_656 3_656 Y
N1 Ni1 N1 180.0 . 3_656 Y
N2 Ni1 N3 90.87(6) . . Y
N2 Ni1 N3 89.13(6) 3_656 . Y
N1 Ni1 N3 90.51(5) . . Y
N1 Ni1 N3 89.49(5) 3_656 . Y
N2 Ni1 N3 89.13(6) . 3_656 Y
N2 Ni1 N3 90.87(6) 3_656 3_656 Y
N1 Ni1 N3 89.49(5) . 3_656 Y
N1 Ni1 N3 90.51(5) 3_656 3_656 Y
N3 Ni1 N3 180.00(8) . 3_656 Y
C1 N1 C5 118.29(14) . . ?
C1 N1 Ni1 113.72(10) . . ?
C5 N1 Ni1 127.99(11) . . ?
C6 N2 Ni1 108.16(10) . . ?
C6 N2 H2A 110.1 . . ?
Ni1 N2 H2A 110.1 . . ?
C6 N2 H2B 110.1 . . ?
Ni1 N2 H2B 110.1 . . ?
H2A N2 H2B 108.4 . . ?
N4 N3 Ni1 123.23(12) . . ?
N5 N4 N3 177.89(19) . . ?
N1 C1 C2 121.95(15) . . ?
N1 C1 C6 116.34(14) . . ?
C2 C1 C6 121.71(15) . . ?
C3 C2 C1 119.25(16) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C2 C3 C4 119.12(16) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C3 C4 C5 118.77(16) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
N1 C5 C4 122.60(16) . . ?
N1 C5 H5 118.7 . . ?
C4 C5 H5 118.7 . . ?
N2 C6 C1 111.36(13) . . ?
N2 C6 H6A 109.4 . . ?
C1 C6 H6A 109.4 . . ?
N2 C6 H6B 109.4 . . ?
C1 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?

_refine_diff_density_max         0.212
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.048

_shelxl_version_number           2014-3

_database_code_depnum_ccdc_archive 'CCDC 974912'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_compd2

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H8 Cu N8'
_chemical_formula_sum            'C6 H8 Cu N8'
_chemical_formula_weight         255.74

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'

_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                   6.9212(5)
_cell_length_b                   8.2733(5)
_cell_length_c                   9.9826(6)
_cell_angle_alpha                67.059(6)
_cell_angle_beta                 72.775(6)
_cell_angle_gamma                65.514(6)
_cell_volume                     472.85(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2091
_cell_measurement_theta_min      2.8500
_cell_measurement_theta_max      31.9590

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.796
_exptl_crystal_F_000             258
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    2.289
_shelx_estimated_absorpt_T_min   0.461
_shelx_estimated_absorpt_T_max   0.657
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.64340
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.0938
_diffrn_reflns_number            3590
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_av_R_equivalents  0.0151
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.843
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1929
_reflns_number_gt                1735
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ORTEP-III
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0353P)²+0.0791P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     DIRECT
_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         1929
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0302
_refine_ls_R_factor_gt           0.0251
_refine_ls_wR_factor_ref         0.0646
_refine_ls_wR_factor_gt          0.0623
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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
Cu1 Cu 0.24452(4) 0.95740(3) 0.06305(3) 0.03086(11) Uani 1 1 d . . . . .
N1 N 0.2453(3) 1.0055(2) 0.24455(19) 0.0285(4) Uani 1 1 d . . . . .
N2 N 0.2669(3) 0.7013(2) 0.2023(2) 0.0332(4) Uani 1 1 d . . . . .
HN2A H 0.1472 0.6799 0.2112 0.040 Uiso 1 1 calc R U . . .
HN2B H 0.3762 0.6178 0.1647 0.040 Uiso 1 1 calc R U . . .
N3 N 0.2932(3) 1.1921(3) -0.0650(2) 0.0409(5) Uani 1 1 d . . . . .
N4 N 0.2295(3) 1.2753(3) -0.1797(2) 0.0373(4) Uani 1 1 d . . . . .
N5 N 0.1729(4) 1.3583(3) -0.2932(3) 0.0598(6) Uani 1 1 d . . . . .
N6 N 0.1929(3) 0.9078(3) -0.1000(2) 0.0430(5) Uani 1 1 d . . . . .
N7 N 0.2665(3) 0.7567(3) -0.1150(2) 0.0370(4) Uani 1 1 d . . . . .
N8 N 0.3305(5) 0.6153(3) -0.1335(3) 0.0685(7) Uani 1 1 d . . . . .
C1 C 0.2207(4) 1.1715(3) 0.2535(3) 0.0372(5) Uani 1 1 d . . . . .
H1 H 0.2024 1.2749 0.1695 0.045 Uiso 1 1 calc R U . . .
C2 C 0.2219(4) 1.1923(4) 0.3831(3) 0.0424(6) Uani 1 1 d . . . . .
H2 H 0.2030 1.3085 0.3870 0.051 Uiso 1 1 calc R U . . .
C3 C 0.2517(3) 1.0385(4) 0.5076(3) 0.0403(5) Uani 1 1 d . . . . .
H3 H 0.2546 1.0495 0.5962 0.048 Uiso 1 1 calc R U . . .
C4 C 0.2770(3) 0.8685(3) 0.4987(3) 0.0378(5) Uani 1 1 d . . . . .
H4 H 0.2966 0.7632 0.5813 0.045 Uiso 1 1 calc R U . . .
C5 C 0.2729(3) 0.8569(3) 0.3656(2) 0.0294(4) Uani 1 1 d . . . . .
C6 C 0.2993(4) 0.6761(3) 0.3483(2) 0.0374(5) Uani 1 1 d . . . . .
H6A H 0.4425 0.5887 0.3642 0.045 Uiso 1 1 calc R U . . .
H6B H 0.1965 0.6231 0.4225 0.045 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
Cu1 N3 1.9673(19) . Y
Cu1 N6 1.9824(19) . Y
Cu1 N2 2.0010(18) . Y
Cu1 N1 2.0026(17) . Y
Cu1 N6 2.721(2) 2_575 Y
Cu1 N3 2.916(2) 2_675 Y
N1 C5 1.338(3) . ?
N1 C1 1.347(3) . ?
N2 C6 1.461(3) . ?
N2 HN2A 0.8900 . ?
N2 HN2B 0.8900 . ?
N3 N4 1.188(3) . ?
N4 N5 1.158(3) . ?
N6 N7 1.191(3) . ?
N7 N8 1.135(3) . ?
C1 C2 1.374(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.381(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.379(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.379(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.502(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?

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 N6 93.46(8) . . Y
N3 Cu1 N2 166.13(8) . . Y
N6 Cu1 N2 93.78(8) . . Y
N3 Cu1 N1 91.89(8) . . Y
N6 Cu1 N1 169.98(8) . . Y
N2 Cu1 N1 82.80(7) . . Y
N3 Cu1 N6 97.52(8) . 2_575 Y
N6 Cu1 N6 79.02(8) . 2_575 Y
N2 Cu1 N6 95.46(7) . 2_575 Y
N1 Cu1 N6 91.90(6) . 2_575 Y
N3 Cu1 N3 85.25(8) . 2_675 Y
N6 Cu1 N3 108.04(8) . 2_675 Y
N2 Cu1 N3 81.27(6) . 2_675 Y
N1 Cu1 N3 80.82(6) . 2_675 Y
N6 Cu1 N3 172.32(6) 2_575 2_675 Y
C5 N1 C1 118.82(18) . . ?
C5 N1 Cu1 115.49(14) . . ?
C1 N1 Cu1 125.69(15) . . ?
C6 N2 Cu1 112.85(14) . . ?
C6 N2 HN2A 109.0 . . ?
Cu1 N2 HN2A 109.0 . . ?
C6 N2 HN2B 109.0 . . ?
Cu1 N2 HN2B 109.0 . . ?
HN2A N2 HN2B 107.8 . . ?
N4 N3 Cu1 121.92(16) . . ?
N5 N4 N3 177.8(2) . . ?
N7 N6 Cu1 122.27(15) . . ?
N8 N7 N6 177.0(2) . . ?
N1 C1 C2 121.9(2) . . ?
N1 C1 H1 119.1 . . ?
C2 C1 H1 119.1 . . ?
C1 C2 C3 119.2(2) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C4 C3 C2 119.1(2) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C5 C4 C3 119.0(2) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
N1 C5 C4 122.1(2) . . ?
N1 C5 C6 116.18(18) . . ?
C4 C5 C6 121.72(19) . . ?
N2 C6 C5 111.98(17) . . ?
N2 C6 H6A 109.2 . . ?
C5 C6 H6A 109.2 . . ?
N2 C6 H6B 109.2 . . ?
C5 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 HN2A N5 0.89 2.23 3.097(3) 164.0 2_575
N2 HN2A N4 0.89 2.57 3.430(2) 161.6 2_575
N2 HN2B N8 0.89 2.19 3.053(3) 163.9 2_665

_refine_diff_density_max         0.350
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.056

_shelxl_version_number           2014-3

_database_code_depnum_ccdc_archive 'CCDC 974913'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_shelx

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H16 Cu N10'
_chemical_formula_sum            'C12 H16 Cu N10'
_chemical_formula_weight         363.89

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'

_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                   8.6111(2)
_cell_length_b                   9.1061(2)
_cell_length_c                   9.3794(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.735(2)
_cell_angle_gamma                90
_cell_volume                     733.91(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    4251
_cell_measurement_theta_min      3.1010
_cell_measurement_theta_max      32.2490

_exptl_crystal_description       block
_exptl_crystal_colour            BLUE
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.647
_exptl_crystal_F_000             374
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    1.505
_shelx_estimated_absorpt_T_min   0.661
_shelx_estimated_absorpt_T_max   0.753
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.98851
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.0938
_diffrn_reflns_number            7628
_diffrn_reflns_av_unetI/netI     0.0208
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.370
_diffrn_reflns_theta_max         30.558
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2238
_reflns_number_gt                1932
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ORTEP-III
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0369P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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         2238
_refine_ls_number_parameters     106
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0311
_refine_ls_R_factor_gt           0.0248
_refine_ls_wR_factor_ref         0.0717
_refine_ls_wR_factor_gt          0.0688
_refine_ls_goodness_of_fit_ref   1.197
_refine_ls_restrained_S_all      1.197
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001

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 0.5000 0.0000 0.0000 0.02290(8) Uani 1 2 d S . P . .
N1 N 0.72110(12) 0.04317(11) 0.07862(11) 0.0204(2) Uani 1 1 d . . . . .
N2 N 0.57771(12) 0.09549(12) -0.17386(10) 0.0244(2) Uani 1 1 d . . . . .
HN2A H 0.6146 0.0277 -0.2311 0.029 Uiso 1 1 calc R U . . .
HN2B H 0.5002 0.1426 -0.2218 0.029 Uiso 1 1 calc R U . . .
N3 N 0.59496(15) -0.24500(14) -0.08364(13) 0.0364(3) Uani 1 1 d . . . . .
N4 N 0.65276(13) -0.33026(13) -0.00264(12) 0.0317(2) Uani 1 1 d . . . . .
N5 N 0.7123(2) -0.4163(2) 0.07512(17) 0.0637(5) Uani 1 1 d . . . . .
C1 C 0.79364(14) 0.14294(12) 0.00122(13) 0.0217(2) Uani 1 1 d . . . . .
C2 C 0.94439(15) 0.18893(14) 0.03918(14) 0.0269(3) Uani 1 1 d . . . . .
H2 H 0.9922 0.2592 -0.0151 0.032 Uiso 1 1 calc R U . . .
C3 C 1.02242(15) 0.12893(14) 0.15867(15) 0.0284(3) Uani 1 1 d . . . . .
H3 H 1.1234 0.1584 0.1861 0.034 Uiso 1 1 calc R U . . .
C4 C 0.94848(17) 0.02454(14) 0.23688(15) 0.0274(3) Uani 1 1 d . . . . .
H4 H 0.9991 -0.0178 0.3173 0.033 Uiso 1 1 calc R U . . .
C5 C 0.79818(17) -0.01599(13) 0.19380(15) 0.0246(3) Uani 1 1 d . . . . .
H5 H 0.7487 -0.0866 0.2463 0.030 Uiso 1 1 calc R U . . .
C6 C 0.70209(15) 0.20007(15) -0.12841(14) 0.0280(3) Uani 1 1 d . . . . .
H6A H 0.6566 0.2943 -0.1068 0.034 Uiso 1 1 calc R U . . .
H6B H 0.7706 0.2142 -0.2053 0.034 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
Cu1 N2 2.0013(10) 3_655 y
Cu1 N2 2.0013(10) . y
Cu1 N1 2.0348(10) . y
Cu1 N1 2.0348(10) 3_655 y
Cu1 N3 2.5189(12) 3_655 y
Cu1 N3 2.5189(12) . y
N1 C5 1.3433(17) . ?
N1 C1 1.3422(14) . ?
N2 C6 1.4752(16) . ?
N2 HN2A 0.8900 . ?
N2 HN2B 0.8900 . ?
N3 N4 1.1741(16) . ?
N4 N5 1.1658(19) . ?
C1 C2 1.3882(17) . ?
C1 C6 1.4985(18) . ?
C2 C3 1.3813(19) . ?
C2 H2 0.9300 . ?
C3 C4 1.3812(19) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(2) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Cu1 N2 180.00(7) 3_655 . y
N2 Cu1 N1 98.24(4) 3_655 . y
N2 Cu1 N1 81.76(4) . . y
N2 Cu1 N1 81.76(4) 3_655 3_655 y
N2 Cu1 N1 98.24(4) . 3_655 y
N1 Cu1 N1 180.00(6) . 3_655 y
N2 Cu1 N3 89.91(4) 3_655 3_655 y
N2 Cu1 N3 90.09(4) . 3_655 y
N1 Cu1 N3 91.78(4) . 3_655 y
N1 Cu1 N3 88.22(4) 3_655 3_655 y
N2 Cu1 N3 90.09(4) 3_655 . y
N2 Cu1 N3 89.91(4) . . y
N1 Cu1 N3 88.22(4) . . y
N1 Cu1 N3 91.78(4) 3_655 . y
N3 Cu1 N3 180.00(7) 3_655 . y
C5 N1 C1 118.91(11) . . ?
C5 N1 Cu1 128.00(9) . . ?
C1 N1 Cu1 113.09(8) . . ?
C6 N2 Cu1 108.66(7) . . ?
C6 N2 HN2A 110.0 . . ?
Cu1 N2 HN2A 110.0 . . ?
C6 N2 HN2B 110.0 . . ?
Cu1 N2 HN2B 110.0 . . ?
HN2A N2 HN2B 108.3 . . ?
N4 N3 Cu1 121.11(9) . . ?
N5 N4 N3 178.33(16) . . ?
N1 C1 C2 121.72(11) . . ?
N1 C1 C6 115.79(10) . . ?
C2 C1 C6 122.49(11) . . ?
C3 C2 C1 119.09(12) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C2 C3 C4 119.10(12) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C5 C4 C3 118.96(13) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
N1 C5 C4 122.19(12) . . ?
N1 C5 H5 118.9 . . ?
C4 C5 H5 118.9 . . ?
N2 C6 C1 110.12(10) . . ?
N2 C6 H6A 109.6 . . ?
C1 C6 H6A 109.6 . . ?
N2 C6 H6B 109.6 . . ?
C1 C6 H6B 109.6 . . ?
H6A C6 H6B 108.2 . . ?

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
N2 HN2A N5 0.89 2.29 3.147(2) 161.8 4
N2 HN2B N3 0.89 2.20 3.0089(16) 150.3 2_654

_refine_diff_density_max         0.282
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.052

_shelxl_version_number           2014-3

_database_code_depnum_ccdc_archive 'CCDC 974914'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_shelx

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H16 Cu3 N22'
_chemical_formula_sum            'C12 H16 Cu3 N22'
_chemical_formula_weight         659.09

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'

_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                   7.4717(15)
_cell_length_b                   8.9361(18)
_cell_length_c                   9.391(2)
_cell_angle_alpha                76.781(18)
_cell_angle_beta                 75.283(18)
_cell_angle_gamma                71.000(19)
_cell_volume                     566.1(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1020
_cell_measurement_theta_min      3.2540
_cell_measurement_theta_max      28.8070

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.933
_exptl_crystal_F_000             329
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    2.848
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.35758
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.0938
_diffrn_reflns_number            3951
_diffrn_reflns_av_unetI/netI     0.0650
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.245
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2307
_reflns_number_gt                1637
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ortep-III
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1118P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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         2307
_refine_ls_number_parameters     169
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0903
_refine_ls_R_factor_gt           0.0646
_refine_ls_wR_factor_ref         0.1958
_refine_ls_wR_factor_gt          0.1653
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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
Cu1 Cu 0.0000 0.5000 0.5000 0.0440(3) Uani 1 2 d S . P . .
Cu2 Cu 0.42883(9) 0.39393(9) 0.29012(8) 0.0452(3) Uani 1 1 d . . . . .
N1 N 0.2988(7) 0.5712(7) 0.4075(6) 0.0482(13) Uani 1 1 d . . . . .
N2 N 0.3673(7) 0.6677(6) 0.4171(5) 0.0443(12) Uani 1 1 d . . . . .
N3 N 0.4363(9) 0.7612(9) 0.4308(9) 0.086(2) Uani 1 1 d . . . . .
N4 N 0.1803(7) 0.3409(8) 0.3619(7) 0.0549(15) Uani 1 1 d . . . . .
N5 N 0.1317(8) 0.2449(8) 0.3199(7) 0.0651(18) Uani 1 1 d . . . . .
N6 N 0.0872(11) 0.1563(12) 0.2808(10) 0.117(4) Uani 1 1 d . . . . .
N7 N 0.6515(7) 0.4796(7) 0.2036(7) 0.0581(15) Uani 1 1 d . . . . .
N8 N 0.7404(9) 0.4530(8) 0.0851(8) 0.081(2) Uani 1 1 d . . . . .
N9 N 0.8221(16) 0.4380(12) -0.0348(12) 0.157(5) Uani 1 1 d . . . . .
N10 N 0.5625(7) 0.1960(7) 0.1969(6) 0.0458(12) Uani 1 1 d . . . . .
C1 C 0.6797(8) 0.0695(8) 0.2685(7) 0.0468(15) Uani 1 1 d . . . . .
H1 H 0.6802 0.0708 0.3672 0.056 Uiso 1 1 calc R U . . .
C2 C 0.7975(8) -0.0600(8) 0.2063(7) 0.0473(15) Uani 1 1 d . . . . .
C3 C 0.7959(9) -0.0617(9) 0.0623(7) 0.0556(17) Uani 1 1 d . . . . .
H3 H 0.8747 -0.1485 0.0160 0.067 Uiso 1 1 calc R U . . .
C4 C 0.6761(10) 0.0671(9) -0.0155(7) 0.0558(18) Uani 1 1 d . . . . .
H4 H 0.6731 0.0677 -0.1141 0.067 Uiso 1 1 calc R U . . .
C5 C 0.5631(9) 0.1924(9) 0.0563(7) 0.0535(17) Uani 1 1 d . . . . .
H5 H 0.4831 0.2789 0.0045 0.064 Uiso 1 1 calc R U . . .
C6 C 0.9276(9) -0.1925(8) 0.2930(9) 0.065(2) Uani 1 1 d . . . . .
H6A H 1.0586 -0.2062 0.2368 0.078 Uiso 1 1 calc R U . . .
H6B H 0.9219 -0.1583 0.3853 0.078 Uiso 1 1 calc R U . . .
N11 N 0.8914(7) -0.3481(7) 0.3305(6) 0.0469(12) Uani 1 1 d . . . . .
H11A H 0.9380 -0.3955 0.2498 0.056 Uiso 1 1 calc R U . . .
H11B H 0.7642 -0.3323 0.3512 0.056 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
Cu1 N11 1.997(5) 2_656 y
Cu1 N11 1.997(5) 1_465 y
Cu1 N4 2.056(5) 2_566 y
Cu1 N4 2.056(5) . y
Cu1 N1 2.415(5) 2_566 y
Cu1 N1 2.415(5) . y
Cu2 N7 1.968(5) . y
Cu2 N4 1.980(5) . y
Cu2 N1 1.980(5) . y
Cu2 N10 2.001(5) . y
N1 N2 1.167(7) . ?
N2 N3 1.159(7) . ?
N4 N5 1.206(7) . ?
N5 N6 1.112(8) . ?
N7 N8 1.175(8) . ?
N8 N9 1.151(10) . ?
N10 C5 1.327(8) . ?
N10 C1 1.343(8) . ?
C1 C2 1.357(9) . ?
C1 H1 0.9300 . ?
C2 C3 1.358(9) . ?
C2 C6 1.490(9) . ?
C3 C4 1.392(10) . ?
C3 H3 0.9300 . ?
C4 C5 1.365(10) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 N11 1.450(8) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
N11 Cu1 1.997(5) 1_645 ?
N11 H11A 0.8900 . ?
N11 H11B 0.8900 . ?

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
N11 Cu1 N11 180.0(2) 2_656 1_465 y
N11 Cu1 N4 92.1(2) 2_656 2_566 y
N11 Cu1 N4 87.9(2) 1_465 2_566 y
N11 Cu1 N4 87.9(2) 2_656 . y
N11 Cu1 N4 92.1(2) 1_465 . y
N4 Cu1 N4 180.0 2_566 . y
N11 Cu1 N1 89.66(19) 2_656 2_566 y
N11 Cu1 N1 90.34(19) 1_465 2_566 y
N4 Cu1 N1 72.0(2) 2_566 2_566 y
N4 Cu1 N1 108.0(2) . 2_566 y
N11 Cu1 N1 90.34(19) 2_656 . y
N11 Cu1 N1 89.66(19) 1_465 . y
N4 Cu1 N1 108.0(2) 2_566 . y
N4 Cu1 N1 72.0(2) . . y
N1 Cu1 N1 180.0(3) 2_566 . y
N7 Cu2 N4 170.8(3) . . y
N7 Cu2 N1 91.7(2) . . y
N4 Cu2 N1 83.8(2) . . y
N7 Cu2 N10 91.3(2) . . y
N4 Cu2 N10 94.1(2) . . y
N1 Cu2 N10 172.6(2) . . y
N2 N1 Cu2 125.2(4) . . ?
N2 N1 Cu1 139.0(4) . . ?
Cu2 N1 Cu1 95.8(2) . . ?
N3 N2 N1 178.0(7) . . ?
N5 N4 Cu2 126.6(4) . . ?
N5 N4 Cu1 124.5(4) . . ?
Cu2 N4 Cu1 108.4(3) . . ?
N6 N5 N4 179.8(9) . . ?
N8 N7 Cu2 118.6(5) . . ?
N9 N8 N7 175.2(10) . . ?
C5 N10 C1 117.2(6) . . ?
C5 N10 Cu2 122.0(5) . . ?
C1 N10 Cu2 120.0(4) . . ?
N10 C1 C2 124.3(6) . . ?
N10 C1 H1 117.9 . . ?
C2 C1 H1 117.9 . . ?
C1 C2 C3 117.7(7) . . ?
C1 C2 C6 120.5(6) . . ?
C3 C2 C6 121.8(6) . . ?
C2 C3 C4 119.8(6) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 118.4(6) . . ?
C5 C4 H4 120.8 . . ?
C3 C4 H4 120.8 . . ?
N10 C5 C4 122.7(7) . . ?
N10 C5 H5 118.6 . . ?
C4 C5 H5 118.6 . . ?
N11 C6 C2 117.9(5) . . ?
N11 C6 H6A 107.8 . . ?
C2 C6 H6A 107.8 . . ?
N11 C6 H6B 107.8 . . ?
C2 C6 H6B 107.8 . . ?
H6A C6 H6B 107.2 . . ?
C6 N11 Cu1 117.3(4) . 1_645 ?
C6 N11 H11A 108.0 . . ?
Cu1 N11 H11A 108.0 1_645 . ?
C6 N11 H11B 108.0 . . ?
Cu1 N11 H11B 108.0 1_645 . ?
H11A N11 H11B 107.2 . . ?

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
N11 H11A N9 0.89 2.35 3.134(10) 147.6 2_755
N11 H11B N3 0.89 2.30 3.168(8) 165.5 1_545

_refine_diff_density_max         1.061
_refine_diff_density_min         -0.792
_refine_diff_density_rms         0.144

_shelxl_version_number           2014-3

_database_code_depnum_ccdc_archive 'CCDC 974915'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_shelx

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H16 N10 Zn1'
_chemical_formula_sum            'C12 H16 N10 Zn1'
_chemical_formula_weight         365.72

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'
Zn Zn 0.2839 1.4301 '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                   8.752(3)
_cell_length_b                   9.098(3)
_cell_length_c                   9.408(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.347(6)
_cell_angle_gamma                90
_cell_volume                     747.0(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    5694
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      28.54

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.626
_exptl_crystal_F_000             376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.440
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.280
_exptl_absorpt_coefficient_mu    1.661
_shelx_estimated_absorpt_T_min   0.529
_shelx_estimated_absorpt_T_max   0.653
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.6374
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7597
_diffrn_reflns_av_unetI/netI     0.0140
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.334
_diffrn_reflns_theta_max         26.367
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1518
_reflns_number_gt                1425
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SMART'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ORTEP-III
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0375P)²+0.1763P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     DIRECT
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.030(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1518
_refine_ls_number_parameters     107
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0228
_refine_ls_R_factor_gt           0.0217
_refine_ls_wR_factor_ref         0.0622
_refine_ls_wR_factor_gt          0.0613
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.082
_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
Zn1 Zn 0.0000 0.0000 0.0000 0.03097(12) Uani 1 2 d S . P . .
N1 N 0.23133(13) 0.04316(13) 0.08490(12) 0.0266(2) Uani 1 1 d . . . . .
N2 N 0.08914(13) 0.10256(13) -0.17603(12) 0.0308(3) Uani 1 1 d . . . . .
HN2A H 0.1242 0.0351 -0.2339 0.037 Uiso 1 1 calc R U . . .
HN2B H 0.0160 0.1538 -0.2246 0.037 Uiso 1 1 calc R U . . .
N3 N -0.07992(15) 0.22281(14) 0.08032(14) 0.0386(3) Uani 1 1 d . . . . .
N4 N -0.14069(14) 0.31202(14) 0.00472(13) 0.0349(3) Uani 1 1 d . . . . .
N5 N -0.2027(2) 0.4019(2) -0.06594(18) 0.0666(5) Uani 1 1 d . . . . .
C1 C 0.30740(19) -0.01487(14) 0.20099(17) 0.0298(3) Uani 1 1 d . . . . .
H1 H 0.2577 -0.0835 0.2544 0.036 Uiso 1 1 calc R U . . .
C2 C 0.45681(19) 0.02342(16) 0.24440(17) 0.0339(3) Uani 1 1 d . . . . .
H2 H 0.5065 -0.0185 0.3253 0.041 Uiso 1 1 calc R U . . .
C3 C 0.53048(16) 0.12539(16) 0.16475(16) 0.0347(3) Uani 1 1 d . . . . .
H3 H 0.6305 0.1539 0.1919 0.042 Uiso 1 1 calc R U . . .
C4 C 0.45383(15) 0.18432(15) 0.04460(15) 0.0322(3) Uani 1 1 d . . . . .
H4 H 0.5018 0.2525 -0.0107 0.039 Uiso 1 1 calc R U . . .
C5 C 0.30356(15) 0.14038(14) 0.00707(14) 0.0272(3) Uani 1 1 d . . . . .
C6 C 0.21439(16) 0.20110(16) -0.12356(15) 0.0339(3) Uani 1 1 d . . . . .
H6A H 0.1720 0.2960 -0.1008 0.041 Uiso 1 1 calc R U . . .
H6B H 0.2833 0.2157 -0.1983 0.041 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 N2 2.1019(12) . Y
Zn1 N2 2.1019(12) 3 Y
Zn1 N1 2.1555(13) 3 Y
Zn1 N1 2.1556(13) . Y
Zn1 N3 2.2912(14) 3 Y
Zn1 N3 2.2912(14) . Y
N1 C5 1.3373(17) . ?
N1 C1 1.343(2) . ?
N2 C6 1.4721(18) . ?
N2 HN2A 0.8900 . ?
N2 HN2B 0.8900 . ?
N3 N4 1.1791(18) . ?
N4 N5 1.162(2) . ?
C1 C2 1.385(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.382(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.379(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.3943(19) . ?
C4 H4 0.9300 . ?
C5 C6 1.5097(19) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Zn1 N2 180.0 . 3 Y
N2 Zn1 N1 100.56(5) . 3 Y
N2 Zn1 N1 79.44(5) 3 3 Y
N2 Zn1 N1 79.44(5) . . Y
N2 Zn1 N1 100.56(5) 3 . Y
N1 Zn1 N1 180.0 3 . Y
N2 Zn1 N3 89.55(5) . 3 Y
N2 Zn1 N3 90.45(5) 3 3 Y
N1 Zn1 N3 91.04(5) 3 3 Y
N1 Zn1 N3 88.96(5) . 3 Y
N2 Zn1 N3 90.45(5) . . Y
N2 Zn1 N3 89.55(5) 3 . Y
N1 Zn1 N3 88.95(5) 3 . Y
N1 Zn1 N3 91.05(5) . . Y
N3 Zn1 N3 180.0 3 . Y
C5 N1 C1 118.65(12) . . ?
C5 N1 Zn1 112.79(9) . . ?
C1 N1 Zn1 128.56(10) . . ?
C6 N2 Zn1 108.52(9) . . ?
C6 N2 HN2A 110.0 . . ?
Zn1 N2 HN2A 110.0 . . ?
C6 N2 HN2B 110.0 . . ?
Zn1 N2 HN2B 110.0 . . ?
HN2A N2 HN2B 108.4 . . ?
N4 N3 Zn1 123.03(10) . . ?
N5 N4 N3 177.76(16) . . ?
N1 C1 C2 122.66(14) . . ?
N1 C1 H1 118.7 . . ?
C2 C1 H1 118.7 . . ?
C3 C2 C1 118.54(14) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C4 C3 C2 119.18(13) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C3 C4 C5 119.16(13) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
N1 C5 C4 121.80(13) . . ?
N1 C5 C6 116.82(12) . . ?
C4 C5 C6 121.38(12) . . ?
N2 C6 C5 112.08(11) . . ?
N2 C6 H6A 109.2 . . ?
C5 C6 H6A 109.2 . . ?
N2 C6 H6B 109.2 . . ?
C5 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 HN2A N5 0.89 2.38 3.253(2) 165.2 2_544
N2 HN2B N3 0.89 2.26 3.0748(18) 152.5 4_565

_refine_diff_density_max         0.229
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.049

_shelxl_version_number           2014-3

_database_code_depnum_ccdc_archive 'CCDC 974916'
