# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 958911'
_audit_update_record             
;
2014-11-27 deposited with the CCDC.
2015-02-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H16 Cu2 I2 N4'
_chemical_formula_weight         633.20

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

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

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

_cell_length_a                   8.9647(4)
_cell_length_b                   9.4112(4)
_cell_length_c                   11.6831(5)
_cell_angle_alpha                100.1740(10)
_cell_angle_beta                 92.6190(10)
_cell_angle_gamma                109.1370(10)
_cell_volume                     910.87(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9221
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      29.22

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.309
_exptl_crystal_F_000             596
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    5.727
_shelx_estimated_absorpt_T_min   0.480
_shelx_estimated_absorpt_T_max   0.725
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6006
_exptl_absorpt_correction_T_max  0.7458
_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            36971
_diffrn_reflns_av_unetI/netI     0.0140
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.782
_diffrn_reflns_theta_max         29.254
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4932
_reflns_number_gt                4448
_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)+(0.0158P)²+1.2641P] 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         4932
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0250
_refine_ls_R_factor_gt           0.0211
_refine_ls_wR_factor_ref         0.0477
_refine_ls_wR_factor_gt          0.0458
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.72955(4) 0.48020(4) 0.65289(3) 0.03508(7) Uani 1 1 d . . . . .
Cu2 Cu 0.43630(4) 0.35220(4) 0.41200(3) 0.04210(8) Uani 1 1 d . . . . .
I1 I 0.84614(2) 0.77526(2) 0.69960(2) 0.03969(5) Uani 1 1 d . . . . .
I2 I 0.40656(2) 0.38074(2) 0.64778(2) 0.03296(5) Uani 1 1 d . . . . .
N1 N 0.8368(2) 0.3715(2) 0.75470(17) 0.0274(4) Uani 1 1 d . . . . .
N2 N 0.8132(2) 0.2369(2) 0.50375(18) 0.0313(4) Uani 1 1 d . . . . .
N3 N 0.7311(2) 0.3299(2) 0.49455(19) 0.0330(4) Uani 1 1 d . . . . .
N4 N 0.6041(2) 0.2498(2) 0.41905(18) 0.0315(4) Uani 1 1 d . . . . .
C1 C 0.7175(3) 0.4580(3) 0.9210(2) 0.0367(5) Uani 1 1 d . . . . .
H1A H 0.6716 0.5084 0.8761 0.044 Uiso 1 1 calc R U . . .
C2 C 0.6927(3) 0.4634(4) 1.0360(2) 0.0424(6) Uani 1 1 d . . . . .
H2A H 0.6287 0.5166 1.0684 0.051 Uiso 1 1 calc R U . . .
C3 C 0.7622(3) 0.3898(4) 1.1059(2) 0.0453(7) Uani 1 1 d . . . . .
H3A H 0.7440 0.3947 1.1840 0.054 Uiso 1 1 calc R U . . .
C4 C 0.8557(3) 0.3120(3) 1.0601(2) 0.0417(6) Uani 1 1 d . . . . .
H4A H 0.9024 0.2648 1.1073 0.050 Uiso 1 1 calc R U . . .
C5 C 0.8831(3) 0.3017(3) 0.9411(2) 0.0329(5) Uani 1 1 d . . . . .
C6 C 0.8129(3) 0.3758(3) 0.8704(2) 0.0288(5) Uani 1 1 d . . . . .
C7 C 0.9766(3) 0.2201(3) 0.8886(3) 0.0399(6) Uani 1 1 d . . . . .
H7A H 1.0234 0.1690 0.9321 0.048 Uiso 1 1 calc R U . . .
C8 C 0.9986(3) 0.2162(3) 0.7742(2) 0.0362(5) Uani 1 1 d . . . . .
H8A H 1.0602 0.1622 0.7388 0.043 Uiso 1 1 calc R U . . .
C9 C 0.9277(3) 0.2941(3) 0.7097(2) 0.0297(5) Uani 1 1 d . . . . .
C10 C 0.9592(3) 0.2949(3) 0.5841(2) 0.0365(6) Uani 1 1 d . . . . .
H10A H 1.0184 0.3990 0.5769 0.044 Uiso 1 1 calc R U . . .
H10B H 1.0243 0.2322 0.5622 0.044 Uiso 1 1 calc R U . . .
C11 C 0.7405(3) 0.0983(3) 0.4357(2) 0.0368(6) Uani 1 1 d . . . . .
H11A H 0.7742 0.0138 0.4274 0.044 Uiso 1 1 calc R U . . .
C12 C 0.6059(3) 0.1064(3) 0.3805(2) 0.0316(5) Uani 1 1 d . . . . .
C13 C 0.4807(3) -0.0093(3) 0.2910(3) 0.0388(6) Uani 1 1 d . . . . .
H13A H 0.3813 0.0096 0.2990 0.047 Uiso 1 1 calc R U . . .
H13B H 0.4656 -0.1110 0.3060 0.047 Uiso 1 1 calc R U . . .
C14 C 0.5208(4) -0.0063(3) 0.1653(3) 0.0487(7) Uani 1 1 d . . . . .
H14A H 0.4278 -0.0715 0.1120 0.058 Uiso 1 1 calc R U . . .
H14B H 0.5447 0.0977 0.1527 0.058 Uiso 1 1 calc R U . . .
C15 C 0.6592(5) -0.0587(4) 0.1356(3) 0.0590(9) Uani 1 1 d . . . . .
H15A H 0.6771 -0.0536 0.0558 0.088 Uiso 1 1 calc R U . . .
H15B H 0.7527 0.0068 0.1864 0.088 Uiso 1 1 calc R U . . .
H15C H 0.6357 -0.1626 0.1457 0.088 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 N1 2.0873(19) . ?
Cu1 N3 2.125(2) . ?
Cu1 I1 2.5711(4) . ?
Cu1 Cu2 2.6702(4) 2_666 ?
Cu1 I2 2.7297(4) . ?
Cu2 N4 2.041(2) . ?
Cu2 I1 2.5893(4) 2_666 ?
Cu2 Cu1 2.6703(4) 2_666 ?
Cu2 I2 2.6791(4) 2_666 ?
Cu2 I2 2.7540(4) . ?
Cu2 Cu2 2.9922(7) 2_666 ?
I1 Cu2 2.5893(4) 2_666 ?
I2 Cu2 2.6791(4) 2_666 ?
N1 C9 1.328(3) . ?
N1 C6 1.374(3) . ?
N2 N3 1.329(3) . ?
N2 C11 1.337(3) . ?
N2 C10 1.460(3) . ?
N3 N4 1.324(3) . ?
N4 C12 1.351(3) . ?
C1 C2 1.366(4) . ?
C1 C6 1.414(3) . ?
C2 C3 1.404(4) . ?
C3 C4 1.352(4) . ?
C4 C5 1.415(4) . ?
C5 C7 1.404(4) . ?
C5 C6 1.417(3) . ?
C7 C8 1.355(4) . ?
C8 C9 1.402(3) . ?
C9 C10 1.508(4) . ?
C11 C12 1.372(3) . ?
C12 C13 1.493(3) . ?
C13 C14 1.530(4) . ?
C14 C15 1.512(5) . ?

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
N1 Cu1 N3 93.18(8) . . ?
N1 Cu1 I1 115.11(6) . . ?
N3 Cu1 I1 127.41(6) . . ?
N1 Cu1 Cu2 161.82(6) . 2_666 ?
N3 Cu1 Cu2 103.72(6) . 2_666 ?
I1 Cu1 Cu2 59.173(11) . 2_666 ?
N1 Cu1 I2 113.01(6) . . ?
N3 Cu1 I2 95.05(6) . . ?
I1 Cu1 I2 110.928(12) . . ?
Cu2 Cu1 I2 59.477(11) 2_666 . ?
N4 Cu2 I1 125.56(6) . 2_666 ?
N4 Cu2 Cu1 161.27(7) . 2_666 ?
I1 Cu2 Cu1 58.506(11) 2_666 2_666 ?
N4 Cu2 I2 103.42(6) . 2_666 ?
I1 Cu2 I2 111.986(13) 2_666 2_666 ?
Cu1 Cu2 I2 61.365(11) 2_666 2_666 ?
N4 Cu2 I2 93.80(6) . . ?
I1 Cu2 I2 107.736(14) 2_666 . ?
Cu1 Cu2 I2 102.193(14) 2_666 . ?
I2 Cu2 I2 113.181(14) 2_666 . ?
N4 Cu2 Cu2 105.59(6) . 2_666 ?
I1 Cu2 Cu2 127.994(19) 2_666 2_666 ?
Cu1 Cu2 Cu2 76.426(15) 2_666 2_666 ?
I2 Cu2 Cu2 57.788(13) 2_666 2_666 ?
I2 Cu2 Cu2 55.394(13) . 2_666 ?
Cu1 I1 Cu2 62.321(11) . 2_666 ?
Cu2 I2 Cu1 59.157(10) 2_666 . ?
Cu2 I2 Cu2 66.819(14) 2_666 . ?
Cu1 I2 Cu2 79.644(11) . . ?
C9 N1 C6 117.9(2) . . ?
C9 N1 Cu1 121.38(17) . . ?
C6 N1 Cu1 120.70(15) . . ?
N3 N2 C11 111.0(2) . . ?
N3 N2 C10 118.5(2) . . ?
C11 N2 C10 130.4(2) . . ?
N4 N3 N2 106.64(19) . . ?
N4 N3 Cu1 124.54(16) . . ?
N2 N3 Cu1 115.09(15) . . ?
N3 N4 C12 109.70(19) . . ?
N3 N4 Cu2 114.49(15) . . ?
C12 N4 Cu2 134.53(16) . . ?
C2 C1 C6 119.9(3) . . ?
C1 C2 C3 121.1(3) . . ?
C4 C3 C2 120.2(3) . . ?
C3 C4 C5 120.7(3) . . ?
C7 C5 C4 123.0(2) . . ?
C7 C5 C6 117.8(2) . . ?
C4 C5 C6 119.1(2) . . ?
N1 C6 C1 119.2(2) . . ?
N1 C6 C5 121.8(2) . . ?
C1 C6 C5 118.9(2) . . ?
C8 C7 C5 119.7(2) . . ?
C7 C8 C9 119.5(2) . . ?
N1 C9 C8 123.2(2) . . ?
N1 C9 C10 117.8(2) . . ?
C8 C9 C10 119.0(2) . . ?
N2 C10 C9 112.5(2) . . ?
N2 C11 C12 105.7(2) . . ?
N4 C12 C11 106.9(2) . . ?
N4 C12 C13 122.1(2) . . ?
C11 C12 C13 130.9(2) . . ?
C12 C13 C14 113.3(2) . . ?
C15 C14 C13 114.3(2) . . ?

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
C11 N2 N3 N4 -0.2(3) . . . . ?
C10 N2 N3 N4 -178.7(2) . . . . ?
C11 N2 N3 Cu1 142.28(19) . . . . ?
C10 N2 N3 Cu1 -36.2(3) . . . . ?
N2 N3 N4 C12 0.0(3) . . . . ?
Cu1 N3 N4 C12 -138.03(19) . . . . ?
N2 N3 N4 Cu2 168.99(16) . . . . ?
Cu1 N3 N4 Cu2 31.0(3) . . . . ?
C6 C1 C2 C3 0.8(4) . . . . ?
C1 C2 C3 C4 0.0(4) . . . . ?
C2 C3 C4 C5 -0.9(4) . . . . ?
C3 C4 C5 C7 -178.8(3) . . . . ?
C3 C4 C5 C6 0.8(4) . . . . ?
C9 N1 C6 C1 179.6(2) . . . . ?
Cu1 N1 C6 C1 -1.5(3) . . . . ?
C9 N1 C6 C5 0.5(3) . . . . ?
Cu1 N1 C6 C5 179.37(17) . . . . ?
C2 C1 C6 N1 -180.0(2) . . . . ?
C2 C1 C6 C5 -0.8(4) . . . . ?
C7 C5 C6 N1 -1.2(3) . . . . ?
C4 C5 C6 N1 179.2(2) . . . . ?
C7 C5 C6 C1 179.7(2) . . . . ?
C4 C5 C6 C1 0.0(4) . . . . ?
C4 C5 C7 C8 -179.5(3) . . . . ?
C6 C5 C7 C8 0.8(4) . . . . ?
C5 C7 C8 C9 0.2(4) . . . . ?
C6 N1 C9 C8 0.6(3) . . . . ?
Cu1 N1 C9 C8 -178.31(18) . . . . ?
C6 N1 C9 C10 -177.6(2) . . . . ?
Cu1 N1 C9 C10 3.5(3) . . . . ?
C7 C8 C9 N1 -0.9(4) . . . . ?
C7 C8 C9 C10 177.2(2) . . . . ?
N3 N2 C10 C9 79.0(3) . . . . ?
C11 N2 C10 C9 -99.1(3) . . . . ?
N1 C9 C10 N2 -57.3(3) . . . . ?
C8 C9 C10 N2 124.5(2) . . . . ?
N3 N2 C11 C12 0.4(3) . . . . ?
C10 N2 C11 C12 178.7(2) . . . . ?
N3 N4 C12 C11 0.3(3) . . . . ?
Cu2 N4 C12 C11 -165.7(2) . . . . ?
N3 N4 C12 C13 -177.7(2) . . . . ?
Cu2 N4 C12 C13 16.3(4) . . . . ?
N2 C11 C12 N4 -0.4(3) . . . . ?
N2 C11 C12 C13 177.3(3) . . . . ?
N4 C12 C13 C14 90.4(3) . . . . ?
C11 C12 C13 C14 -87.0(4) . . . . ?
C12 C13 C14 C15 67.8(3) . . . . ?

_refine_diff_density_max         1.491
_refine_diff_density_min         -1.252
_refine_diff_density_rms         0.080

_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_3
_database_code_depnum_ccdc_archive 'CCDC 958912'
_audit_update_record             
;
2014-11-27 deposited with the CCDC.
2015-02-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H18 Cu2 I2 N4'
_chemical_formula_weight         647.22

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      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                   9.0803(4)
_cell_length_b                   9.5611(4)
_cell_length_c                   11.9245(5)
_cell_angle_alpha                101.5650(10)
_cell_angle_beta                 91.6880(10)
_cell_angle_gamma                110.3570(10)
_cell_volume                     945.33(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9522
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      28.31

_exptl_crystal_description       PLATE
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.274
_exptl_crystal_F_000             612
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    5.521
_shelx_estimated_absorpt_T_min   0.288
_shelx_estimated_absorpt_T_max   0.809
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5075
_exptl_absorpt_correction_T_max  0.7457
_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            32549
_diffrn_reflns_av_unetI/netI     0.0138
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.753
_diffrn_reflns_theta_max         28.323
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4680
_reflns_number_gt                4260
_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)+(0.0197P)²+1.0167P] 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         4680
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0229
_refine_ls_R_factor_gt           0.0199
_refine_ls_wR_factor_ref         0.0479
_refine_ls_wR_factor_gt          0.0463
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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 0.72644(4) 0.48877(4) 0.65396(3) 0.03763(7) Uani 1 1 d . . . . .
Cu2 Cu 0.43363(4) 0.34497(4) 0.41310(3) 0.04520(9) Uani 1 1 d . . . . .
I1 I 0.84795(2) 0.78260(2) 0.69572(2) 0.03991(5) Uani 1 1 d . . . . .
I2 I 0.40758(2) 0.38931(2) 0.64670(2) 0.03493(5) Uani 1 1 d . . . . .
N1 N 0.8348(2) 0.3868(2) 0.75349(17) 0.0296(4) Uani 1 1 d . . . . .
N2 N 0.8136(2) 0.2499(2) 0.50451(17) 0.0337(4) Uani 1 1 d . . . . .
N3 N 0.7274(2) 0.3358(2) 0.49672(18) 0.0355(4) Uani 1 1 d . . . . .
N4 N 0.6018(2) 0.2499(2) 0.42247(18) 0.0337(4) Uani 1 1 d . . . . .
C1 C 0.7193(3) 0.4732(3) 0.9201(2) 0.0370(5) Uani 1 1 d . . . . .
H1A H 0.6781 0.5262 0.8785 0.044 Uiso 1 1 calc R U . . .
C2 C 0.6930(3) 0.4769(3) 1.0326(2) 0.0423(6) Uani 1 1 d . . . . .
H2A H 0.6331 0.5320 1.0669 0.051 Uiso 1 1 calc R U . . .
C3 C 0.7552(3) 0.3986(3) 1.0974(2) 0.0449(6) Uani 1 1 d . . . . .
H3A H 0.7362 0.4022 1.1739 0.054 Uiso 1 1 calc R U . . .
C4 C 0.8425(3) 0.3182(3) 1.0491(2) 0.0413(6) Uani 1 1 d . . . . .
H4A H 0.8842 0.2679 1.0930 0.050 Uiso 1 1 calc R U . . .
C5 C 0.8712(3) 0.3099(3) 0.9322(2) 0.0327(5) Uani 1 1 d . . . . .
C6 C 0.8087(3) 0.3890(3) 0.8669(2) 0.0297(4) Uani 1 1 d . . . . .
C7 C 0.9584(3) 0.2254(3) 0.8771(2) 0.0408(6) Uani 1 1 d . . . . .
H7A H 0.9979 0.1695 0.9169 0.049 Uiso 1 1 calc R U . . .
C8 C 0.9849(3) 0.2257(3) 0.7657(2) 0.0379(5) Uani 1 1 d . . . . .
H8A H 1.0438 0.1713 0.7289 0.045 Uiso 1 1 calc R U . . .
C9 C 0.9221(3) 0.3090(3) 0.7068(2) 0.0316(5) Uani 1 1 d . . . . .
C10 C 0.9574(3) 0.3144(3) 0.5846(2) 0.0394(6) Uani 1 1 d . . . . .
H10A H 1.0129 0.4198 0.5803 0.047 Uiso 1 1 calc R U . . .
H10B H 1.0260 0.2576 0.5622 0.047 Uiso 1 1 calc R U . . .
C11 C 0.7450(3) 0.1095(3) 0.4371(2) 0.0398(6) Uani 1 1 d . . . . .
H11A H 0.7817 0.0289 0.4283 0.048 Uiso 1 1 calc R U . . .
C12 C 0.6091(3) 0.1095(3) 0.3837(2) 0.0346(5) Uani 1 1 d . . . . .
C13 C 0.4880(3) -0.0123(3) 0.2953(3) 0.0431(6) Uani 1 1 d . . . . .
H13A H 0.3900 0.0071 0.2973 0.052 Uiso 1 1 calc R U . . .
H13B H 0.4683 -0.1102 0.3154 0.052 Uiso 1 1 calc R U . . .
C14 C 0.5349(3) -0.0232(3) 0.1730(3) 0.0460(6) Uani 1 1 d . . . . .
H14A H 0.4445 -0.0946 0.1205 0.055 Uiso 1 1 calc R U . . .
H14B H 0.5593 0.0763 0.1547 0.055 Uiso 1 1 calc R U . . .
C15 C 0.6736(4) -0.0732(4) 0.1513(3) 0.0529(7) Uani 1 1 d . . . . .
H15A H 0.6578 -0.1642 0.1809 0.063 Uiso 1 1 calc R U . . .
H15B H 0.7686 0.0068 0.1933 0.063 Uiso 1 1 calc R U . . .
C16 C 0.6978(4) -0.1076(4) 0.0246(3) 0.0584(8) Uani 1 1 d . . . . .
H16A H 0.7873 -0.1388 0.0160 0.088 Uiso 1 1 calc R U . . .
H16B H 0.6052 -0.1884 -0.0173 0.088 Uiso 1 1 calc R U . . .
H16C H 0.7161 -0.0174 -0.0050 0.088 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 N1 2.0950(19) . ?
Cu1 N3 2.137(2) . ?
Cu1 I1 2.5706(4) . ?
Cu1 Cu2 2.7069(4) 2_666 ?
Cu1 I2 2.7077(4) . ?
Cu2 N4 2.041(2) . ?
Cu2 I1 2.5902(4) 2_666 ?
Cu2 I2 2.6982(4) 2_666 ?
Cu2 Cu1 2.7069(4) 2_666 ?
Cu2 I2 2.7622(4) . ?
I1 Cu2 2.5901(4) 2_666 ?
I2 Cu2 2.6982(4) 2_666 ?
N1 C9 1.328(3) . ?
N1 C6 1.377(3) . ?
N2 N3 1.330(3) . ?
N2 C11 1.339(3) . ?
N2 C10 1.459(3) . ?
N3 N4 1.326(3) . ?
N4 C12 1.354(3) . ?
C1 C2 1.365(4) . ?
C1 C6 1.411(3) . ?
C2 C3 1.406(4) . ?
C3 C4 1.350(4) . ?
C4 C5 1.417(4) . ?
C5 C7 1.405(4) . ?
C5 C6 1.418(3) . ?
C7 C8 1.357(4) . ?
C8 C9 1.403(3) . ?
C9 C10 1.509(4) . ?
C11 C12 1.372(3) . ?
C12 C13 1.492(3) . ?
C13 C14 1.525(4) . ?
C14 C15 1.508(4) . ?
C15 C16 1.520(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
N1 Cu1 N3 93.22(8) . . ?
N1 Cu1 I1 114.98(5) . . ?
N3 Cu1 I1 125.86(6) . . ?
N1 Cu1 Cu2 163.09(6) . 2_666 ?
N3 Cu1 Cu2 102.99(6) . 2_666 ?
I1 Cu1 Cu2 58.717(11) . 2_666 ?
N1 Cu1 I2 114.66(6) . . ?
N3 Cu1 I2 94.82(6) . . ?
I1 Cu1 I2 111.275(12) . . ?
Cu2 Cu1 I2 59.777(11) 2_666 . ?
N4 Cu2 I1 127.83(6) . 2_666 ?
N4 Cu2 I2 103.02(6) . 2_666 ?
I1 Cu2 I2 110.966(13) 2_666 2_666 ?
N4 Cu2 Cu1 160.18(6) . 2_666 ?
I1 Cu2 Cu1 58.011(11) 2_666 2_666 ?
I2 Cu2 Cu1 60.125(11) 2_666 2_666 ?
N4 Cu2 I2 93.68(6) . . ?
I1 Cu2 I2 108.398(14) 2_666 . ?
I2 Cu2 I2 111.532(13) 2_666 . ?
Cu1 Cu2 I2 102.127(14) 2_666 . ?
Cu1 I1 Cu2 63.272(11) . 2_666 ?
Cu2 I2 Cu1 60.097(10) 2_666 . ?
Cu2 I2 Cu2 68.469(13) 2_666 . ?
Cu1 I2 Cu2 81.042(11) . . ?
C9 N1 C6 117.9(2) . . ?
C9 N1 Cu1 120.82(16) . . ?
C6 N1 Cu1 121.17(15) . . ?
N3 N2 C11 111.1(2) . . ?
N3 N2 C10 118.6(2) . . ?
C11 N2 C10 130.2(2) . . ?
N4 N3 N2 106.81(19) . . ?
N4 N3 Cu1 125.43(16) . . ?
N2 N3 Cu1 114.90(15) . . ?
N3 N4 C12 109.31(19) . . ?
N3 N4 Cu2 114.41(15) . . ?
C12 N4 Cu2 135.45(17) . . ?
C2 C1 C6 120.1(2) . . ?
C1 C2 C3 120.8(3) . . ?
C4 C3 C2 120.4(3) . . ?
C3 C4 C5 120.6(2) . . ?
C7 C5 C4 123.0(2) . . ?
C7 C5 C6 118.0(2) . . ?
C4 C5 C6 119.0(2) . . ?
N1 C6 C1 119.5(2) . . ?
N1 C6 C5 121.6(2) . . ?
C1 C6 C5 119.0(2) . . ?
C8 C7 C5 119.9(2) . . ?
C7 C8 C9 119.1(2) . . ?
N1 C9 C8 123.5(2) . . ?
N1 C9 C10 117.5(2) . . ?
C8 C9 C10 119.0(2) . . ?
N2 C10 C9 111.8(2) . . ?
N2 C11 C12 105.5(2) . . ?
N4 C12 C11 107.3(2) . . ?
N4 C12 C13 122.5(2) . . ?
C11 C12 C13 130.1(2) . . ?
C12 C13 C14 114.0(2) . . ?
C15 C14 C13 115.6(2) . . ?
C14 C15 C16 113.2(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
C11 N2 N3 N4 -0.5(3) . . . . ?
C10 N2 N3 N4 -177.6(2) . . . . ?
C11 N2 N3 Cu1 143.43(18) . . . . ?
C10 N2 N3 Cu1 -33.8(3) . . . . ?
N2 N3 N4 C12 0.1(3) . . . . ?
Cu1 N3 N4 C12 -138.90(18) . . . . ?
N2 N3 N4 Cu2 171.34(15) . . . . ?
Cu1 N3 N4 Cu2 32.3(2) . . . . ?
C6 C1 C2 C3 0.5(4) . . . . ?
C1 C2 C3 C4 0.1(4) . . . . ?
C2 C3 C4 C5 -0.8(4) . . . . ?
C3 C4 C5 C7 -178.7(3) . . . . ?
C3 C4 C5 C6 0.9(4) . . . . ?
C9 N1 C6 C1 178.7(2) . . . . ?
Cu1 N1 C6 C1 -5.9(3) . . . . ?
C9 N1 C6 C5 -0.6(3) . . . . ?
Cu1 N1 C6 C5 174.86(17) . . . . ?
C2 C1 C6 N1 -179.7(2) . . . . ?
C2 C1 C6 C5 -0.4(4) . . . . ?
C7 C5 C6 N1 -1.4(3) . . . . ?
C4 C5 C6 N1 179.0(2) . . . . ?
C7 C5 C6 C1 179.3(2) . . . . ?
C4 C5 C6 C1 -0.3(3) . . . . ?
C4 C5 C7 C8 -178.3(2) . . . . ?
C6 C5 C7 C8 2.2(4) . . . . ?
C5 C7 C8 C9 -1.0(4) . . . . ?
C6 N1 C9 C8 2.0(3) . . . . ?
Cu1 N1 C9 C8 -173.53(18) . . . . ?
C6 N1 C9 C10 -176.7(2) . . . . ?
Cu1 N1 C9 C10 7.8(3) . . . . ?
C7 C8 C9 N1 -1.2(4) . . . . ?
C7 C8 C9 C10 177.5(2) . . . . ?
N3 N2 C10 C9 79.5(3) . . . . ?
C11 N2 C10 C9 -97.1(3) . . . . ?
N1 C9 C10 N2 -61.8(3) . . . . ?
C8 C9 C10 N2 119.5(2) . . . . ?
N3 N2 C11 C12 0.6(3) . . . . ?
C10 N2 C11 C12 177.4(2) . . . . ?
N3 N4 C12 C11 0.3(3) . . . . ?
Cu2 N4 C12 C11 -168.3(2) . . . . ?
N3 N4 C12 C13 -177.6(2) . . . . ?
Cu2 N4 C12 C13 13.8(4) . . . . ?
N2 C11 C12 N4 -0.5(3) . . . . ?
N2 C11 C12 C13 177.1(3) . . . . ?
N4 C12 C13 C14 97.1(3) . . . . ?
C11 C12 C13 C14 -80.2(4) . . . . ?
C12 C13 C14 C15 66.0(3) . . . . ?
C13 C14 C15 C16 170.4(3) . . . . ?

_refine_diff_density_max         0.760
_refine_diff_density_min         -0.746
_refine_diff_density_rms         0.075

_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_1
_database_code_depnum_ccdc_archive 'CCDC 1036540'
_audit_update_record             
;
2014-11-27 deposited with the CCDC.
2015-02-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H10 Cu2 I2 N4'
_chemical_formula_weight         591.12

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

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

_cell_length_a                   8.2321(4)
_cell_length_b                   8.4671(4)
_cell_length_c                   11.9898(5)
_cell_angle_alpha                94.0260(10)
_cell_angle_beta                 95.0450(10)
_cell_angle_gamma                115.8530(10)
_cell_volume                     743.64(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9850
_cell_measurement_theta_min      2.77
_cell_measurement_theta_max      30.57

_exptl_crystal_description       Plate
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.640
_exptl_crystal_F_000             548
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    7.004
_shelx_estimated_absorpt_T_min   0.199
_shelx_estimated_absorpt_T_max   0.640
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4016
_exptl_absorpt_correction_T_max  0.7461
_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            31822
_diffrn_reflns_av_unetI/netI     0.0152
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.718
_diffrn_reflns_theta_max         30.588
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4533
_reflns_number_gt                4430
_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)+(0.0134P)²+1.3280P] 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         4533
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0194
_refine_ls_R_factor_gt           0.0188
_refine_ls_wR_factor_ref         0.0443
_refine_ls_wR_factor_gt          0.0440
_refine_ls_goodness_of_fit_ref   1.195
_refine_ls_restrained_S_all      1.195
_refine_ls_shift/su_max          0.004
_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 0.69746(4) 1.20861(3) 0.69698(2) 0.01397(5) Uani 1 1 d . . . . .
Cu2 Cu 0.45797(4) 1.10575(4) 0.42559(2) 0.01584(6) Uani 1 1 d . . . . .
I1 I 0.82119(2) 0.98227(2) 0.72375(2) 0.01671(4) Uani 1 1 d . . . . .
I2 I 0.33779(2) 1.05774(2) 0.63385(2) 0.01281(4) Uani 1 1 d . . . . .
N1 N 0.7965(2) 1.4225(2) 0.82210(15) 0.0140(3) Uani 1 1 d . . . . .
N2 N 0.8793(3) 1.5395(2) 0.59623(15) 0.0144(3) Uani 1 1 d . . . . .
N3 N 0.7619(3) 1.3690(2) 0.56788(16) 0.0148(3) Uani 1 1 d . . . . .
N4 N 0.6521(3) 1.3588(2) 0.47734(15) 0.0141(3) Uani 1 1 d . . . . .
C1 C 0.5863(3) 1.2469(3) 0.94253(19) 0.0181(4) Uani 1 1 d . . . . .
H1A H 0.5430 1.1472 0.8868 0.022 Uiso 1 1 calc R U . . .
C2 C 0.5130(3) 1.2322(3) 1.0419(2) 0.0223(5) Uani 1 1 d . . . . .
H2A H 0.4193 1.1219 1.0546 0.027 Uiso 1 1 calc R U . . .
C3 C 0.5754(4) 1.3790(4) 1.1256(2) 0.0245(5) Uani 1 1 d . . . . .
H3A H 0.5221 1.3673 1.1936 0.029 Uiso 1 1 calc R U . . .
C4 C 0.7122(4) 1.5383(4) 1.1093(2) 0.0232(5) Uani 1 1 d . . . . .
H4A H 0.7540 1.6362 1.1662 0.028 Uiso 1 1 calc R U . . .
C5 C 0.7917(3) 1.5575(3) 1.00788(18) 0.0170(4) Uani 1 1 d . . . . .
C6 C 0.7263(3) 1.4105(3) 0.92282(18) 0.0149(4) Uani 1 1 d . . . . .
C7 C 0.9343(3) 1.7176(3) 0.9871(2) 0.0200(4) Uani 1 1 d . . . . .
H7A H 0.9823 1.8181 1.0425 0.024 Uiso 1 1 calc R U . . .
C8 C 1.0030(3) 1.7274(3) 0.88652(19) 0.0178(4) Uani 1 1 d . . . . .
H8A H 1.0992 1.8343 0.8715 0.021 Uiso 1 1 calc R U . . .
C9 C 0.9292(3) 1.5764(3) 0.80559(18) 0.0139(4) Uani 1 1 d . . . . .
C10 C 1.0123(3) 1.5861(3) 0.69728(19) 0.0171(4) Uani 1 1 d . . . . .
H10A H 1.1091 1.7076 0.6968 0.020 Uiso 1 1 calc R U . . .
H10B H 1.0698 1.5049 0.6949 0.020 Uiso 1 1 calc R U . . .
C11 C 0.8478(3) 1.6416(3) 0.52448(18) 0.0164(4) Uani 1 1 d . . . . .
H11A H 0.9118 1.7662 0.5257 0.020 Uiso 1 1 calc R U . . .
C12 C 0.7012(3) 1.5234(3) 0.44873(18) 0.0157(4) Uani 1 1 d . . . . .
H12A H 0.6443 1.5531 0.3868 0.019 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 N1 2.0764(18) . ?
Cu1 N3 2.0816(19) . ?
Cu1 I1 2.5582(3) . ?
Cu1 Cu2 2.6517(4) 2_676 ?
Cu1 I2 2.6726(3) . ?
Cu2 N4 2.0450(19) . ?
Cu2 I1 2.5764(3) 2_676 ?
Cu2 Cu1 2.6517(4) 2_676 ?
Cu2 I2 2.7117(3) 2_676 ?
Cu2 I2 2.7578(3) . ?
Cu2 Cu2 2.8604(6) 2_676 ?
I1 Cu2 2.5764(3) 2_676 ?
I2 Cu2 2.7117(3) 2_676 ?
N1 C9 1.328(3) . ?
N1 C6 1.375(3) . ?
N2 N3 1.338(2) . ?
N2 C11 1.347(3) . ?
N2 C10 1.465(3) . ?
N3 N4 1.322(3) . ?
N4 C12 1.351(3) . ?
C1 C2 1.372(3) . ?
C1 C6 1.416(3) . ?
C2 C3 1.412(4) . ?
C3 C4 1.370(4) . ?
C4 C5 1.417(3) . ?
C5 C7 1.410(3) . ?
C5 C6 1.421(3) . ?
C7 C8 1.369(3) . ?
C8 C9 1.410(3) . ?
C9 C10 1.511(3) . ?
C11 C12 1.382(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Cu1 N3 93.14(7) . . ?
N1 Cu1 I1 115.40(5) . . ?
N3 Cu1 I1 122.16(6) . . ?
N1 Cu1 Cu2 167.27(5) . 2_676 ?
N3 Cu1 Cu2 99.39(5) . 2_676 ?
I1 Cu1 Cu2 59.244(10) . 2_676 ?
N1 Cu1 I2 115.57(5) . . ?
N3 Cu1 I2 95.35(5) . . ?
I1 Cu1 I2 112.706(11) . . ?
Cu2 Cu1 I2 61.233(9) 2_676 . ?
N4 Cu2 I1 125.18(6) . 2_676 ?
N4 Cu2 Cu1 157.10(5) . 2_676 ?
I1 Cu2 Cu1 58.569(9) 2_676 2_676 ?
N4 Cu2 I2 101.97(6) . 2_676 ?
I1 Cu2 I2 110.857(11) 2_676 2_676 ?
Cu1 Cu2 I2 59.765(9) 2_676 2_676 ?
N4 Cu2 I2 93.56(5) . . ?
I1 Cu2 I2 107.995(11) 2_676 . ?
Cu1 Cu2 I2 106.844(12) 2_676 . ?
I2 Cu2 I2 116.941(11) 2_676 . ?
N4 Cu2 Cu2 104.86(6) . 2_676 ?
I1 Cu2 Cu2 129.446(16) 2_676 2_676 ?
Cu1 Cu2 Cu2 78.580(13) 2_676 2_676 ?
I2 Cu2 Cu2 59.258(11) 2_676 2_676 ?
I2 Cu2 Cu2 57.683(10) . 2_676 ?
Cu1 I1 Cu2 62.186(10) . 2_676 ?
Cu1 I2 Cu2 59.003(9) . 2_676 ?
Cu1 I2 Cu2 80.083(9) . . ?
Cu2 I2 Cu2 63.058(11) 2_676 . ?
C9 N1 C6 118.25(19) . . ?
C9 N1 Cu1 120.17(15) . . ?
C6 N1 Cu1 121.58(15) . . ?
N3 N2 C11 111.18(19) . . ?
N3 N2 C10 117.84(18) . . ?
C11 N2 C10 130.94(19) . . ?
N4 N3 N2 107.45(18) . . ?
N4 N3 Cu1 127.11(14) . . ?
N2 N3 Cu1 117.39(14) . . ?
N3 N4 C12 108.50(18) . . ?
N3 N4 Cu2 112.39(14) . . ?
C12 N4 Cu2 139.08(16) . . ?
C2 C1 C6 120.1(2) . . ?
C1 C2 C3 120.8(2) . . ?
C4 C3 C2 120.4(2) . . ?
C3 C4 C5 120.3(2) . . ?
C7 C5 C4 122.7(2) . . ?
C7 C5 C6 118.0(2) . . ?
C4 C5 C6 119.3(2) . . ?
N1 C6 C1 119.1(2) . . ?
N1 C6 C5 121.7(2) . . ?
C1 C6 C5 119.2(2) . . ?
C8 C7 C5 119.6(2) . . ?
C7 C8 C9 119.1(2) . . ?
N1 C9 C8 123.3(2) . . ?
N1 C9 C10 117.93(19) . . ?
C8 C9 C10 118.6(2) . . ?
N2 C10 C9 113.08(18) . . ?
N2 C11 C12 104.11(19) . . ?
N4 C12 C11 108.8(2) . . ?

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
C11 N2 N3 N4 -0.3(2) . . . . ?
C10 N2 N3 N4 177.97(18) . . . . ?
C11 N2 N3 Cu1 -151.31(15) . . . . ?
C10 N2 N3 Cu1 26.9(2) . . . . ?
N2 N3 N4 C12 0.1(2) . . . . ?
Cu1 N3 N4 C12 147.52(16) . . . . ?
N2 N3 N4 Cu2 -178.23(13) . . . . ?
Cu1 N3 N4 Cu2 -30.8(2) . . . . ?
C6 C1 C2 C3 0.1(4) . . . . ?
C1 C2 C3 C4 -0.9(4) . . . . ?
C2 C3 C4 C5 0.4(4) . . . . ?
C3 C4 C5 C7 -179.2(2) . . . . ?
C3 C4 C5 C6 0.8(4) . . . . ?
C9 N1 C6 C1 -179.2(2) . . . . ?
Cu1 N1 C6 C1 1.6(3) . . . . ?
C9 N1 C6 C5 0.2(3) . . . . ?
Cu1 N1 C6 C5 -178.92(16) . . . . ?
C2 C1 C6 N1 -179.4(2) . . . . ?
C2 C1 C6 C5 1.1(4) . . . . ?
C7 C5 C6 N1 -1.0(3) . . . . ?
C4 C5 C6 N1 179.0(2) . . . . ?
C7 C5 C6 C1 178.5(2) . . . . ?
C4 C5 C6 C1 -1.6(3) . . . . ?
C4 C5 C7 C8 -179.2(2) . . . . ?
C6 C5 C7 C8 0.8(3) . . . . ?
C5 C7 C8 C9 0.1(4) . . . . ?
C6 N1 C9 C8 0.7(3) . . . . ?
Cu1 N1 C9 C8 179.90(17) . . . . ?
C6 N1 C9 C10 176.9(2) . . . . ?
Cu1 N1 C9 C10 -3.9(3) . . . . ?
C7 C8 C9 N1 -0.9(4) . . . . ?
C7 C8 C9 C10 -177.1(2) . . . . ?
N3 N2 C10 C9 -73.7(3) . . . . ?
C11 N2 C10 C9 104.1(3) . . . . ?
N1 C9 C10 N2 59.0(3) . . . . ?
C8 C9 C10 N2 -124.6(2) . . . . ?
N3 N2 C11 C12 0.3(2) . . . . ?
C10 N2 C11 C12 -177.6(2) . . . . ?
N3 N4 C12 C11 0.0(2) . . . . ?
Cu2 N4 C12 C11 177.72(18) . . . . ?
N2 C11 C12 N4 -0.2(2) . . . . ?

_refine_diff_density_max         2.006
_refine_diff_density_min         -0.739
_refine_diff_density_rms         0.112

_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_4
_database_code_depnum_ccdc_archive 'CCDC 1036541'
_audit_update_record             
;
2014-11-27 deposited with the CCDC.
2015-02-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H18 Cu2 I2 N4'
_chemical_formula_weight         647.22

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

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

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

_cell_length_a                   8.9132(4)
_cell_length_b                   9.2024(5)
_cell_length_c                   12.2475(6)
_cell_angle_alpha                97.9620(10)
_cell_angle_beta                 96.1670(10)
_cell_angle_gamma                105.4290(10)
_cell_volume                     948.02(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    9911
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      33.24

_exptl_crystal_description       PLATE
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.267
_exptl_crystal_F_000             612
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    5.505
_shelx_estimated_absorpt_T_min   0.437
_shelx_estimated_absorpt_T_max   0.810
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5626
_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            51585
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.698
_diffrn_reflns_theta_max         33.291
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7269
_reflns_number_gt                6253
_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)+(0.0297P)²+0.4989P] 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         7269
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0306
_refine_ls_R_factor_gt           0.0237
_refine_ls_wR_factor_ref         0.0588
_refine_ls_wR_factor_gt          0.0557
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.72609(3) 0.47530(3) 0.65268(2) 0.01878(5) Uani 1 1 d . . . . .
Cu2 Cu 0.41861(3) 0.34551(3) 0.43079(2) 0.02052(6) Uani 1 1 d . . . . .
I1 I 0.87139(2) 0.76178(2) 0.66460(2) 0.02020(4) Uani 1 1 d . . . . .
I2 I 0.41245(2) 0.41442(2) 0.65442(2) 0.01641(3) Uani 1 1 d . . . . .
N1 N 0.8354(2) 0.3674(2) 0.76096(14) 0.0164(3) Uani 1 1 d . . . . .
N2 N 0.8004(2) 0.2132(2) 0.52463(14) 0.0175(3) Uani 1 1 d . . . . .
N3 N 0.7094(2) 0.3064(2) 0.51659(14) 0.0178(3) Uani 1 1 d . . . . .
N4 N 0.5835(2) 0.2314(2) 0.44286(14) 0.0162(3) Uani 1 1 d . . . . .
C1 C 0.7293(3) 0.4778(3) 0.91356(19) 0.0252(4) Uani 1 1 d . . . . .
H1A H 0.6824 0.5310 0.8652 0.030 Uiso 1 1 calc R U . . .
C2 C 0.7120(3) 0.4946(3) 1.0248(2) 0.0328(6) Uani 1 1 d . . . . .
H2A H 0.6519 0.5589 1.0523 0.039 Uiso 1 1 calc R U . . .
C3 C 0.7817(3) 0.4183(3) 1.0977(2) 0.0354(6) Uani 1 1 d . . . . .
H3A H 0.7698 0.4325 1.1743 0.042 Uiso 1 1 calc R U . . .
C4 C 0.8663(3) 0.3241(3) 1.05986(19) 0.0315(6) Uani 1 1 d . . . . .
H4A H 0.9130 0.2729 1.1100 0.038 Uiso 1 1 calc R U . . .
C5 C 0.8853(3) 0.3018(3) 0.94558(18) 0.0217(4) Uani 1 1 d . . . . .
C6 C 0.8169(2) 0.3813(2) 0.87206(16) 0.0177(4) Uani 1 1 d . . . . .
C7 C 0.9708(3) 0.2058(3) 0.9019(2) 0.0276(5) Uani 1 1 d . . . . .
H7A H 1.0161 0.1494 0.9486 0.033 Uiso 1 1 calc R U . . .
C8 C 0.9888(3) 0.1935(3) 0.7918(2) 0.0253(4) Uani 1 1 d . . . . .
H8A H 1.0475 0.1295 0.7615 0.030 Uiso 1 1 calc R U . . .
C9 C 0.9192(2) 0.2768(2) 0.72377(17) 0.0180(4) Uani 1 1 d . . . . .
C10 C 0.9467(2) 0.2680(3) 0.60346(17) 0.0234(4) Uani 1 1 d . . . . .
H10A H 1.0053 0.3709 0.5918 0.028 Uiso 1 1 calc R U . . .
H10B H 1.0127 0.1985 0.5883 0.028 Uiso 1 1 calc R U . . .
C11 C 0.7349(2) 0.0780(3) 0.45580(17) 0.0188(4) Uani 1 1 d . . . . .
H11A H 0.7757 -0.0076 0.4461 0.023 Uiso 1 1 calc R U . . .
C12 C 0.5954(2) 0.0905(2) 0.40238(15) 0.0143(3) Uani 1 1 d . . . . .
C13 C 0.4734(2) -0.0219(2) 0.31583(16) 0.0167(3) Uani 1 1 d . . . . .
H13A H 0.3698 -0.0049 0.3239 0.020 Uiso 1 1 calc R U . . .
H13B H 0.4680 -0.1264 0.3300 0.020 Uiso 1 1 calc R U . . .
C14 C 0.5027(2) -0.0138(2) 0.19453(17) 0.0194(4) Uani 1 1 d . . . . .
H14A H 0.4213 -0.1018 0.1456 0.023 Uiso 1 1 calc R U . . .
C15 C 0.4789(3) 0.1321(3) 0.1595(2) 0.0301(5) Uani 1 1 d . . . . .
H15A H 0.3747 0.1402 0.1727 0.045 Uiso 1 1 calc R U . . .
H15B H 0.5601 0.2210 0.2031 0.045 Uiso 1 1 calc R U . . .
H15C H 0.4866 0.1289 0.0800 0.045 Uiso 1 1 calc R U . . .
C16 C 0.6622(3) -0.0334(3) 0.1762(2) 0.0286(5) Uani 1 1 d . . . . .
H16A H 0.6724 -0.1283 0.1997 0.043 Uiso 1 1 calc R U . . .
H16B H 0.6718 -0.0384 0.0969 0.043 Uiso 1 1 calc R U . . .
H16C H 0.7454 0.0537 0.2200 0.043 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 N1 2.0726(17) . ?
Cu1 N3 2.0791(17) . ?
Cu1 I1 2.5855(3) . ?
Cu1 Cu2 2.5966(4) 2_666 ?
Cu1 I2 2.7041(3) . ?
Cu2 N4 2.0253(17) . ?
Cu2 I1 2.5875(3) 2_666 ?
Cu2 Cu1 2.5967(4) 2_666 ?
Cu2 I2 2.7282(3) 2_666 ?
Cu2 I2 2.7343(3) . ?
Cu2 Cu2 3.0009(6) 2_666 ?
I1 Cu2 2.5874(3) 2_666 ?
I2 Cu2 2.7282(3) 2_666 ?
N1 C9 1.327(3) . ?
N1 C6 1.381(3) . ?
N2 N3 1.334(2) . ?
N2 C11 1.348(3) . ?
N2 C10 1.460(3) . ?
N3 N4 1.322(2) . ?
N4 C12 1.358(3) . ?
C1 C2 1.379(3) . ?
C1 C6 1.408(3) . ?
C2 C3 1.402(4) . ?
C3 C4 1.359(4) . ?
C4 C5 1.421(3) . ?
C5 C7 1.401(4) . ?
C5 C6 1.421(3) . ?
C7 C8 1.368(3) . ?
C8 C9 1.409(3) . ?
C9 C10 1.514(3) . ?
C11 C12 1.382(3) . ?
C12 C13 1.492(3) . ?
C13 C14 1.544(3) . ?
C14 C16 1.516(3) . ?
C14 C15 1.525(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Cu1 N3 92.61(7) . . ?
N1 Cu1 I1 113.86(5) . . ?
N3 Cu1 I1 124.18(5) . . ?
N1 Cu1 Cu2 163.88(5) . 2_666 ?
N3 Cu1 Cu2 103.09(5) . 2_666 ?
I1 Cu1 Cu2 59.907(9) . 2_666 ?
N1 Cu1 I2 113.45(5) . . ?
N3 Cu1 I2 95.63(5) . . ?
I1 Cu1 I2 114.473(10) . . ?
Cu2 Cu1 I2 61.914(9) 2_666 . ?
N4 Cu2 I1 127.57(5) . 2_666 ?
N4 Cu2 Cu1 155.45(5) . 2_666 ?
I1 Cu2 Cu1 59.832(9) 2_666 2_666 ?
N4 Cu2 I2 97.91(5) . 2_666 ?
I1 Cu2 I2 113.594(10) 2_666 2_666 ?
Cu1 Cu2 I2 60.977(9) 2_666 2_666 ?
N4 Cu2 I2 96.75(5) . . ?
I1 Cu2 I2 106.688(11) 2_666 . ?
Cu1 Cu2 I2 103.056(11) 2_666 . ?
I2 Cu2 I2 113.355(10) 2_666 . ?
N4 Cu2 Cu2 103.43(5) . 2_666 ?
I1 Cu2 Cu2 128.722(15) 2_666 2_666 ?
Cu1 Cu2 Cu2 76.394(12) 2_666 2_666 ?
I2 Cu2 Cu2 56.774(10) 2_666 2_666 ?
I2 Cu2 Cu2 56.580(9) . 2_666 ?
Cu1 I1 Cu2 60.261(9) . 2_666 ?
Cu1 I2 Cu2 57.108(8) . 2_666 ?
Cu1 I2 Cu2 79.453(9) . . ?
Cu2 I2 Cu2 66.646(10) 2_666 . ?
C9 N1 C6 118.15(18) . . ?
C9 N1 Cu1 120.53(14) . . ?
C6 N1 Cu1 121.24(14) . . ?
N3 N2 C11 110.92(16) . . ?
N3 N2 C10 118.16(17) . . ?
C11 N2 C10 130.91(18) . . ?
N4 N3 N2 107.22(16) . . ?
N4 N3 Cu1 127.78(14) . . ?
N2 N3 Cu1 118.41(12) . . ?
N3 N4 C12 109.41(16) . . ?
N3 N4 Cu2 113.28(13) . . ?
C12 N4 Cu2 137.00(14) . . ?
C2 C1 C6 119.7(2) . . ?
C1 C2 C3 120.9(2) . . ?
C4 C3 C2 120.6(2) . . ?
C3 C4 C5 120.3(2) . . ?
C7 C5 C4 122.8(2) . . ?
C7 C5 C6 118.1(2) . . ?
C4 C5 C6 119.1(2) . . ?
N1 C6 C1 119.13(19) . . ?
N1 C6 C5 121.5(2) . . ?
C1 C6 C5 119.3(2) . . ?
C8 C7 C5 119.7(2) . . ?
C7 C8 C9 119.2(2) . . ?
N1 C9 C8 123.2(2) . . ?
N1 C9 C10 118.13(18) . . ?
C8 C9 C10 118.6(2) . . ?
N2 C10 C9 112.75(17) . . ?
N2 C11 C12 105.15(18) . . ?
N4 C12 C11 107.29(17) . . ?
N4 C12 C13 122.86(17) . . ?
C11 C12 C13 129.85(18) . . ?
C12 C13 C14 114.69(16) . . ?
C16 C14 C15 112.2(2) . . ?
C16 C14 C13 111.92(18) . . ?
C15 C14 C13 111.25(18) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 N2 N3 N4 0.4(2) . . . . ?
C10 N2 N3 N4 -178.56(17) . . . . ?
C11 N2 N3 Cu1 154.17(14) . . . . ?
C10 N2 N3 Cu1 -24.8(2) . . . . ?
N2 N3 N4 C12 -0.9(2) . . . . ?
Cu1 N3 N4 C12 -151.44(14) . . . . ?
N2 N3 N4 Cu2 173.79(12) . . . . ?
Cu1 N3 N4 Cu2 23.3(2) . . . . ?
C6 C1 C2 C3 0.7(4) . . . . ?
C1 C2 C3 C4 -0.9(4) . . . . ?
C2 C3 C4 C5 0.1(4) . . . . ?
C3 C4 C5 C7 -179.8(2) . . . . ?
C3 C4 C5 C6 1.0(3) . . . . ?
C9 N1 C6 C1 179.51(19) . . . . ?
Cu1 N1 C6 C1 -3.7(3) . . . . ?
C9 N1 C6 C5 0.1(3) . . . . ?
Cu1 N1 C6 C5 176.97(15) . . . . ?
C2 C1 C6 N1 -179.0(2) . . . . ?
C2 C1 C6 C5 0.4(3) . . . . ?
C7 C5 C6 N1 -1.1(3) . . . . ?
C4 C5 C6 N1 178.12(19) . . . . ?
C7 C5 C6 C1 179.5(2) . . . . ?
C4 C5 C6 C1 -1.2(3) . . . . ?
C4 C5 C7 C8 -177.8(2) . . . . ?
C6 C5 C7 C8 1.3(3) . . . . ?
C5 C7 C8 C9 -0.7(3) . . . . ?
C6 N1 C9 C8 0.6(3) . . . . ?
Cu1 N1 C9 C8 -176.28(16) . . . . ?
C6 N1 C9 C10 -176.86(18) . . . . ?
Cu1 N1 C9 C10 6.3(3) . . . . ?
C7 C8 C9 N1 -0.3(3) . . . . ?
C7 C8 C9 C10 177.1(2) . . . . ?
N3 N2 C10 C9 71.7(3) . . . . ?
C11 N2 C10 C9 -107.1(2) . . . . ?
N1 C9 C10 N2 -60.1(3) . . . . ?
C8 C9 C10 N2 122.4(2) . . . . ?
N3 N2 C11 C12 0.2(2) . . . . ?
C10 N2 C11 C12 179.1(2) . . . . ?
N3 N4 C12 C11 1.1(2) . . . . ?
Cu2 N4 C12 C11 -171.79(16) . . . . ?
N3 N4 C12 C13 -178.87(17) . . . . ?
Cu2 N4 C12 C13 8.2(3) . . . . ?
N2 C11 C12 N4 -0.8(2) . . . . ?
N2 C11 C12 C13 179.16(19) . . . . ?
N4 C12 C13 C14 91.8(2) . . . . ?
C11 C12 C13 C14 -88.2(3) . . . . ?
C12 C13 C14 C16 56.4(2) . . . . ?
C12 C13 C14 C15 -70.0(2) . . . . ?

_refine_diff_density_max         1.716
_refine_diff_density_min         -0.993
_refine_diff_density_rms         0.129

_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 1036542'
_audit_update_record             
;
2014-11-27 deposited with the CCDC.
2015-02-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H12 Cu2 I2 N4 O'
_chemical_formula_weight         621.15

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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                   7.8794(7)
_cell_length_b                   8.6744(7)
_cell_length_c                   13.0228(11)
_cell_angle_alpha                78.570(2)
_cell_angle_beta                 76.751(2)
_cell_angle_gamma                67.049(2)
_cell_volume                     791.92(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9856
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      28.32

_exptl_crystal_description       PLATE
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.605
_exptl_crystal_F_000             580
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    6.589
_shelx_estimated_absorpt_T_min   0.313
_shelx_estimated_absorpt_T_max   0.827
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5142
_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            27766
_diffrn_reflns_av_unetI/netI     0.0145
_diffrn_reflns_av_R_equivalents  0.0230
_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       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.618
_diffrn_reflns_theta_max         28.330
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3949
_reflns_number_gt                3716
_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)+(0.0180P)²+0.8266P] 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         3949
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0176
_refine_ls_R_factor_gt           0.0159
_refine_ls_wR_factor_ref         0.0385
_refine_ls_wR_factor_gt          0.0378
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_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 0.50582(4) 0.20438(3) 0.30888(2) 0.01387(6) Uani 1 1 d . . . . .
Cu2 Cu 0.35363(4) 0.09371(3) 0.58201(2) 0.01669(6) Uani 1 1 d . . . . .
I1 I 0.84221(2) 0.00814(2) 0.25017(2) 0.01721(4) Uani 1 1 d . . . . .
I2 I 0.27809(2) 0.03153(2) 0.40237(2) 0.01282(4) Uani 1 1 d . . . . .
N1 N 0.3932(2) 0.4025(2) 0.19645(14) 0.0120(3) Uani 1 1 d . . . . .
N2 N 0.3607(2) 0.5265(2) 0.39863(14) 0.0118(3) Uani 1 1 d . . . . .
N3 N 0.4190(2) 0.3613(2) 0.43111(14) 0.0127(3) Uani 1 1 d . . . . .
N4 N 0.3140(2) 0.3400(2) 0.52450(14) 0.0117(3) Uani 1 1 d . . . . .
C1 C 0.3524(3) 0.2126(3) 0.09937(18) 0.0179(4) Uani 1 1 d . . . . .
H1A H 0.4002 0.1212 0.1515 0.021 Uiso 1 1 calc R U . . .
C2 C 0.2994(3) 0.1853(3) 0.01335(19) 0.0216(5) Uani 1 1 d . . . . .
H2A H 0.3092 0.0747 0.0070 0.026 Uiso 1 1 calc R U . . .
C3 C 0.2306(3) 0.3185(3) -0.06568(18) 0.0219(5) Uani 1 1 d . . . . .
H3A H 0.1966 0.2969 -0.1254 0.026 Uiso 1 1 calc R U . . .
C4 C 0.2127(3) 0.4782(3) -0.05670(17) 0.0194(4) Uani 1 1 d . . . . .
H4A H 0.1655 0.5677 -0.1100 0.023 Uiso 1 1 calc R U . . .
C5 C 0.2640(3) 0.5117(3) 0.03177(16) 0.0145(4) Uani 1 1 d . . . . .
C6 C 0.3360(3) 0.3766(3) 0.11029(16) 0.0131(4) Uani 1 1 d . . . . .
C7 C 0.2457(3) 0.6752(3) 0.04486(18) 0.0177(4) Uani 1 1 d . . . . .
H7A H 0.1963 0.7682 -0.0059 0.021 Uiso 1 1 calc R U . . .
C8 C 0.2999(3) 0.6986(3) 0.13135(17) 0.0157(4) Uani 1 1 d . . . . .
H8A H 0.2864 0.8083 0.1420 0.019 Uiso 1 1 calc R U . . .
C9 C 0.3757(3) 0.5584(3) 0.20418(16) 0.0125(4) Uani 1 1 d . . . . .
C10 C 0.4485(3) 0.5846(3) 0.29481(16) 0.0144(4) Uani 1 1 d . . . . .
H10A H 0.5853 0.5230 0.2864 0.017 Uiso 1 1 calc R U . . .
H10B H 0.4250 0.7061 0.2915 0.017 Uiso 1 1 calc R U . . .
C11 C 0.2176(3) 0.6127(3) 0.46893(16) 0.0134(4) Uani 1 1 d . . . . .
H11A H 0.1510 0.7311 0.4637 0.016 Uiso 1 1 calc R U . . .
C12 C 0.1883(3) 0.4927(2) 0.55008(16) 0.0108(4) Uani 1 1 d . . . . .
C13 C 0.0508(3) 0.5136(3) 0.65128(17) 0.0141(4) Uani 1 1 d . . . . .
H13A H -0.0768 0.5774 0.6349 0.017 Uiso 1 1 calc R U . . .
H13B H 0.0548 0.4012 0.6881 0.017 Uiso 1 1 calc R U . . .
O1 O 0.0899(2) 0.6005(2) 0.71955(12) 0.0198(3) Uani 1 1 d . . . . .
H1B H 0.0104 0.6106 0.7756 0.030 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 N1 2.0719(18) . ?
Cu1 N3 2.1187(18) . ?
Cu1 I1 2.5644(3) . ?
Cu1 Cu2 2.6388(4) 2_656 ?
Cu1 I2 2.7062(3) . ?
Cu2 N4 2.0432(17) . ?
Cu2 I1 2.5866(3) 2_656 ?
Cu2 Cu1 2.6388(4) 2_656 ?
Cu2 I2 2.7141(4) 2_656 ?
Cu2 I2 2.7399(4) . ?
Cu2 Cu2 2.9529(6) 2_656 ?
I1 Cu2 2.5865(3) 2_656 ?
I2 Cu2 2.7141(4) 2_656 ?
N1 C9 1.327(3) . ?
N1 C6 1.387(3) . ?
N2 N3 1.333(2) . ?
N2 C11 1.345(3) . ?
N2 C10 1.461(3) . ?
N3 N4 1.329(2) . ?
N4 C12 1.360(3) . ?
C1 C2 1.373(3) . ?
C1 C6 1.410(3) . ?
C1 H1A 0.9500 . ?
C2 C3 1.409(4) . ?
C2 H2A 0.9500 . ?
C3 C4 1.363(4) . ?
C3 H3A 0.9500 . ?
C4 C5 1.419(3) . ?
C4 H4A 0.9500 . ?
C5 C7 1.409(3) . ?
C5 C6 1.419(3) . ?
C7 C8 1.368(3) . ?
C7 H7A 0.9500 . ?
C8 C9 1.404(3) . ?
C8 H8A 0.9500 . ?
C9 C10 1.514(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.376(3) . ?
C11 H11A 0.9500 . ?
C12 C13 1.493(3) . ?
C13 O1 1.423(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
O1 H1B 0.8400 . ?

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
N1 Cu1 N3 93.40(7) . . ?
N1 Cu1 I1 115.56(5) . . ?
N3 Cu1 I1 125.35(5) . . ?
N1 Cu1 Cu2 165.61(5) . 2_656 ?
N3 Cu1 Cu2 100.20(5) . 2_656 ?
I1 Cu1 Cu2 59.597(9) . 2_656 ?
N1 Cu1 I2 113.62(5) . . ?
N3 Cu1 I2 94.18(5) . . ?
I1 Cu1 I2 112.206(12) . . ?
Cu2 Cu1 I2 61.018(10) 2_656 . ?
N4 Cu2 I1 125.32(5) . 2_656 ?
N4 Cu2 Cu1 158.10(5) . 2_656 ?
I1 Cu2 Cu1 58.771(10) 2_656 2_656 ?
N4 Cu2 I2 101.38(5) . 2_656 ?
I1 Cu2 I2 111.250(11) 2_656 2_656 ?
Cu1 Cu2 I2 60.718(9) 2_656 2_656 ?
N4 Cu2 I2 92.92(5) . . ?
I1 Cu2 I2 110.509(12) 2_656 . ?
Cu1 Cu2 I2 105.745(12) 2_656 . ?
I2 Cu2 I2 114.441(10) 2_656 . ?
N4 Cu2 Cu2 103.22(5) . 2_656 ?
I1 Cu2 Cu2 131.163(16) 2_656 2_656 ?
Cu1 Cu2 Cu2 78.594(13) 2_656 2_656 ?
I2 Cu2 Cu2 57.640(10) 2_656 2_656 ?
I2 Cu2 Cu2 56.801(11) . 2_656 ?
Cu1 I1 Cu2 61.632(10) . 2_656 ?
Cu1 I2 Cu2 58.264(9) . 2_656 ?
Cu1 I2 Cu2 81.352(10) . . ?
Cu2 I2 Cu2 65.559(10) 2_656 . ?
C9 N1 C6 117.86(18) . . ?
C9 N1 Cu1 120.78(14) . . ?
C6 N1 Cu1 121.36(14) . . ?
N3 N2 C11 111.19(17) . . ?
N3 N2 C10 118.24(17) . . ?
C11 N2 C10 130.46(18) . . ?
N4 N3 N2 106.93(16) . . ?
N4 N3 Cu1 125.55(13) . . ?
N2 N3 Cu1 115.18(13) . . ?
N3 N4 C12 109.09(17) . . ?
N3 N4 Cu2 114.30(13) . . ?
C12 N4 Cu2 135.89(14) . . ?
C2 C1 C6 119.9(2) . . ?
C2 C1 H1A 120.0 . . ?
C6 C1 H1A 120.0 . . ?
C1 C2 C3 121.0(2) . . ?
C1 C2 H2A 119.5 . . ?
C3 C2 H2A 119.5 . . ?
C4 C3 C2 120.1(2) . . ?
C4 C3 H3A 119.9 . . ?
C2 C3 H3A 119.9 . . ?
C3 C4 C5 120.4(2) . . ?
C3 C4 H4A 119.8 . . ?
C5 C4 H4A 119.8 . . ?
C7 C5 C4 122.3(2) . . ?
C7 C5 C6 118.47(19) . . ?
C4 C5 C6 119.2(2) . . ?
N1 C6 C1 119.51(19) . . ?
N1 C6 C5 121.23(19) . . ?
C1 C6 C5 119.25(19) . . ?
C8 C7 C5 119.4(2) . . ?
C8 C7 H7A 120.3 . . ?
C5 C7 H7A 120.3 . . ?
C7 C8 C9 119.1(2) . . ?
C7 C8 H8A 120.4 . . ?
C9 C8 H8A 120.4 . . ?
N1 C9 C8 123.84(19) . . ?
N1 C9 C10 117.70(18) . . ?
C8 C9 C10 118.42(19) . . ?
N2 C10 C9 112.45(17) . . ?
N2 C10 H10A 109.1 . . ?
C9 C10 H10A 109.1 . . ?
N2 C10 H10B 109.1 . . ?
C9 C10 H10B 109.1 . . ?
H10A C10 H10B 107.8 . . ?
N2 C11 C12 105.23(18) . . ?
N2 C11 H11A 127.4 . . ?
C12 C11 H11A 127.4 . . ?
N4 C12 C11 107.56(18) . . ?
N4 C12 C13 122.76(18) . . ?
C11 C12 C13 129.67(18) . . ?
O1 C13 C12 111.53(17) . . ?
O1 C13 H13A 109.3 . . ?
C12 C13 H13A 109.3 . . ?
O1 C13 H13B 109.3 . . ?
C12 C13 H13B 109.3 . . ?
H13A C13 H13B 108.0 . . ?
C13 O1 H1B 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 N2 N3 N4 -0.8(2) . . . . ?
C10 N2 N3 N4 -177.46(17) . . . . ?
C11 N2 N3 Cu1 143.72(14) . . . . ?
C10 N2 N3 Cu1 -32.9(2) . . . . ?
N2 N3 N4 C12 0.5(2) . . . . ?
Cu1 N3 N4 C12 -139.30(15) . . . . ?
N2 N3 N4 Cu2 172.39(12) . . . . ?
Cu1 N3 N4 Cu2 32.6(2) . . . . ?
C6 C1 C2 C3 0.9(3) . . . . ?
C1 C2 C3 C4 -1.2(4) . . . . ?
C2 C3 C4 C5 0.4(3) . . . . ?
C3 C4 C5 C7 -179.2(2) . . . . ?
C3 C4 C5 C6 0.6(3) . . . . ?
C9 N1 C6 C1 -179.98(19) . . . . ?
Cu1 N1 C6 C1 0.8(3) . . . . ?
C9 N1 C6 C5 1.1(3) . . . . ?
Cu1 N1 C6 C5 -178.15(15) . . . . ?
C2 C1 C6 N1 -178.8(2) . . . . ?
C2 C1 C6 C5 0.1(3) . . . . ?
C7 C5 C6 N1 -2.1(3) . . . . ?
C4 C5 C6 N1 178.05(18) . . . . ?
C7 C5 C6 C1 178.99(19) . . . . ?
C4 C5 C6 C1 -0.9(3) . . . . ?
C4 C5 C7 C8 -179.2(2) . . . . ?
C6 C5 C7 C8 0.9(3) . . . . ?
C5 C7 C8 C9 1.1(3) . . . . ?
C6 N1 C9 C8 1.1(3) . . . . ?
Cu1 N1 C9 C8 -179.67(15) . . . . ?
C6 N1 C9 C10 -176.56(18) . . . . ?
Cu1 N1 C9 C10 2.7(2) . . . . ?
C7 C8 C9 N1 -2.2(3) . . . . ?
C7 C8 C9 C10 175.40(19) . . . . ?
N3 N2 C10 C9 77.9(2) . . . . ?
C11 N2 C10 C9 -97.9(2) . . . . ?
N1 C9 C10 N2 -58.1(2) . . . . ?
C8 C9 C10 N2 124.1(2) . . . . ?
N3 N2 C11 C12 0.8(2) . . . . ?
C10 N2 C11 C12 176.89(19) . . . . ?
N3 N4 C12 C11 -0.1(2) . . . . ?
Cu2 N4 C12 C11 -169.37(15) . . . . ?
N3 N4 C12 C13 -178.99(18) . . . . ?
Cu2 N4 C12 C13 11.7(3) . . . . ?
N2 C11 C12 N4 -0.4(2) . . . . ?
N2 C11 C12 C13 178.4(2) . . . . ?
N4 C12 C13 O1 112.5(2) . . . . ?
C11 C12 C13 O1 -66.2(3) . . . . ?

_refine_diff_density_max         0.830
_refine_diff_density_min         -0.828
_refine_diff_density_rms         0.096

_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_6
_database_code_depnum_ccdc_archive 'CCDC 1036543'
_audit_update_record             
;
2014-11-27 deposited with the CCDC.
2015-02-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H14 Cu2 I2 N4 O'
_chemical_formula_weight         635.17

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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           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                   21.4131(8)
_cell_length_b                   4.2319(2)
_cell_length_c                   19.1375(7)
_cell_angle_alpha                90
_cell_angle_beta                 105.3020(10)
_cell_angle_gamma                90
_cell_volume                     1672.72(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9353
_cell_measurement_theta_min      3.33
_cell_measurement_theta_max      36.30

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.522
_exptl_crystal_F_000             1192
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    6.241
_shelx_estimated_absorpt_T_min   0.179
_shelx_estimated_absorpt_T_max   0.475
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3988
_exptl_absorpt_correction_T_max  0.7471
_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            61124
_diffrn_reflns_av_unetI/netI     0.0156
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_k_min       -2
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.972
_diffrn_reflns_theta_max         36.345
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             8082
_reflns_number_gt                7555
_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)+(0.0154P)²+3.6657P] 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         8082
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0277
_refine_ls_R_factor_gt           0.0249
_refine_ls_wR_factor_ref         0.0544
_refine_ls_wR_factor_gt          0.0531
_refine_ls_goodness_of_fit_ref   1.187
_refine_ls_restrained_S_all      1.187
_refine_ls_shift/su_max          0.010
_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 0.29588(2) 0.01754(6) 0.94321(2) 0.01192(4) Uani 1 1 d . . . . .
Cu2 Cu 0.18497(2) 0.47231(6) 1.01354(2) 0.01454(4) Uani 1 1 d . . . . .
I1 I 0.31661(2) 0.53408(3) 1.02602(2) 0.00994(2) Uani 1 1 d . . . . .
I2 I 0.14907(2) 0.95414(3) 1.07298(2) 0.01318(3) Uani 1 1 d . . . . .
N1 N 0.32293(7) 0.0668(4) 0.84706(8) 0.0112(2) Uani 1 1 d . . . . .
N2 N 0.17657(7) 0.0690(4) 0.82004(8) 0.0113(2) Uani 1 1 d . . . . .
N3 N 0.20029(7) 0.1339(4) 0.89026(8) 0.0112(2) Uani 1 1 d . . . . .
N4 N 0.16050(7) 0.3348(4) 0.90854(8) 0.0108(2) Uani 1 1 d . . . . .
C1 C 0.43098(9) 0.2217(5) 0.91113(10) 0.0164(3) Uani 1 1 d . . . . .
H1A H 0.4254 0.1270 0.9541 0.020 Uiso 1 1 calc R U . . .
C2 C 0.48849(10) 0.3665(6) 0.91147(12) 0.0205(4) Uani 1 1 d . . . . .
H2A H 0.5229 0.3658 0.9545 0.025 Uiso 1 1 calc R U . . .
C3 C 0.49711(10) 0.5161(6) 0.84884(13) 0.0214(4) Uani 1 1 d . . . . .
H3A H 0.5367 0.6205 0.8505 0.026 Uiso 1 1 calc R U . . .
C4 C 0.44877(10) 0.5117(5) 0.78575(12) 0.0189(4) Uani 1 1 d . . . . .
H4A H 0.4548 0.6147 0.7439 0.023 Uiso 1 1 calc R U . . .
C5 C 0.38952(9) 0.3533(5) 0.78263(10) 0.0133(3) Uani 1 1 d . . . . .
C6 C 0.38009(8) 0.2140(5) 0.84659(9) 0.0118(3) Uani 1 1 d . . . . .
C7 C 0.33985(10) 0.3232(5) 0.71765(10) 0.0163(3) Uani 1 1 d . . . . .
H7A H 0.3443 0.4174 0.6742 0.020 Uiso 1 1 calc R U . . .
C8 C 0.28524(9) 0.1561(5) 0.71829(10) 0.0149(3) Uani 1 1 d . . . . .
H8A H 0.2525 0.1214 0.6746 0.018 Uiso 1 1 calc R U . . .
C9 C 0.27823(8) 0.0365(4) 0.78430(9) 0.0116(3) Uani 1 1 d . . . . .
C10 C 0.21607(9) -0.1309(5) 0.78582(10) 0.0138(3) Uani 1 1 d . . . . .
H10A H 0.1913 -0.1824 0.7357 0.017 Uiso 1 1 calc R U . . .
H10B H 0.2265 -0.3312 0.8131 0.017 Uiso 1 1 calc R U . . .
C11 C 0.12051(8) 0.2277(5) 0.79214(10) 0.0125(3) Uani 1 1 d . . . . .
H11A H 0.0942 0.2235 0.7437 0.015 Uiso 1 1 calc R U . . .
C12 C 0.11011(8) 0.3968(4) 0.84970(9) 0.0111(3) Uani 1 1 d . . . . .
C13 C 0.05667(9) 0.6127(5) 0.85652(11) 0.0145(3) Uani 1 1 d . . . . .
H13A H 0.0343 0.6943 0.8079 0.017 Uiso 1 1 calc R U . . .
H13B H 0.0757 0.7955 0.8870 0.017 Uiso 1 1 calc R U . . .
C14 C 0.00703(9) 0.4554(5) 0.88933(11) 0.0164(3) Uani 1 1 d . . . . .
H14A H 0.0293 0.3287 0.9322 0.020 Uiso 1 1 calc R U . . .
H14B H -0.0196 0.6180 0.9050 0.020 Uiso 1 1 calc R U . . .
O1 O -0.03304(7) 0.2565(4) 0.83570(9) 0.0201(3) Uani 1 1 d . . . . .
H1B H -0.0607 0.1675 0.8530 0.030 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 N1 2.0801(15) . ?
Cu1 N3 2.0891(15) . ?
Cu1 I1 2.5541(3) 1_545 ?
Cu1 I1 2.6676(3) . ?
Cu2 N4 2.0237(16) . ?
Cu2 I2 2.5503(3) . ?
Cu2 I2 2.6749(3) 1_545 ?
Cu2 I1 2.7779(3) . ?
I1 Cu1 2.5541(3) 1_565 ?
I2 Cu2 2.6749(3) 1_565 ?
N1 C9 1.330(2) . ?
N1 C6 1.376(2) . ?
N2 N3 1.334(2) . ?
N2 C11 1.356(2) . ?
N2 C10 1.467(2) . ?
N3 N4 1.315(2) . ?
N4 C12 1.364(2) . ?
C1 C2 1.374(3) . ?
C1 C6 1.415(3) . ?
C1 H1A 0.9500 . ?
C2 C3 1.410(3) . ?
C2 H2A 0.9500 . ?
C3 C4 1.368(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.422(3) . ?
C4 H4A 0.9500 . ?
C5 C7 1.413(3) . ?
C5 C6 1.420(3) . ?
C7 C8 1.369(3) . ?
C7 H7A 0.9500 . ?
C8 C9 1.405(3) . ?
C8 H8A 0.9500 . ?
C9 C10 1.515(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.380(3) . ?
C11 H11A 0.9500 . ?
C12 C13 1.497(3) . ?
C13 C14 1.523(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 O1 1.426(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
O1 H1B 0.8400 . ?

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
N1 Cu1 N3 90.75(6) . . ?
N1 Cu1 I1 125.86(5) . 1_545 ?
N3 Cu1 I1 118.52(5) . 1_545 ?
N1 Cu1 I1 113.70(5) . . ?
N3 Cu1 I1 94.77(5) . . ?
I1 Cu1 I1 108.261(9) 1_545 . ?
N4 Cu2 I2 130.03(5) . . ?
N4 Cu2 I2 99.12(5) . 1_545 ?
I2 Cu2 I2 108.149(10) . 1_545 ?
N4 Cu2 I1 95.93(4) . . ?
I2 Cu2 I1 107.752(10) . . ?
I2 Cu2 I1 116.079(10) 1_545 . ?
Cu1 I1 Cu1 108.259(10) 1_565 . ?
Cu1 I1 Cu2 90.905(8) 1_565 . ?
Cu1 I1 Cu2 82.288(8) . . ?
Cu2 I2 Cu2 108.150(10) . 1_565 ?
C9 N1 C6 117.85(15) . . ?
C9 N1 Cu1 119.16(12) . . ?
C6 N1 Cu1 120.48(12) . . ?
N3 N2 C11 110.91(15) . . ?
N3 N2 C10 117.22(15) . . ?
C11 N2 C10 131.64(16) . . ?
N4 N3 N2 107.46(14) . . ?
N4 N3 Cu1 130.11(12) . . ?
N2 N3 Cu1 120.27(11) . . ?
N3 N4 C12 109.37(15) . . ?
N3 N4 Cu2 115.72(11) . . ?
C12 N4 Cu2 134.89(12) . . ?
C2 C1 C6 119.81(19) . . ?
C2 C1 H1A 120.1 . . ?
C6 C1 H1A 120.1 . . ?
C1 C2 C3 120.96(19) . . ?
C1 C2 H2A 119.5 . . ?
C3 C2 H2A 119.5 . . ?
C4 C3 C2 120.39(19) . . ?
C4 C3 H3A 119.8 . . ?
C2 C3 H3A 119.8 . . ?
C3 C4 C5 120.18(19) . . ?
C3 C4 H4A 119.9 . . ?
C5 C4 H4A 119.9 . . ?
C7 C5 C6 118.43(17) . . ?
C7 C5 C4 122.38(17) . . ?
C6 C5 C4 119.18(17) . . ?
N1 C6 C1 119.08(16) . . ?
N1 C6 C5 121.52(16) . . ?
C1 C6 C5 119.39(17) . . ?
C8 C7 C5 119.02(17) . . ?
C8 C7 H7A 120.5 . . ?
C5 C7 H7A 120.5 . . ?
C7 C8 C9 119.21(17) . . ?
C7 C8 H8A 120.4 . . ?
C9 C8 H8A 120.4 . . ?
N1 C9 C8 123.73(17) . . ?
N1 C9 C10 117.02(16) . . ?
C8 C9 C10 119.24(16) . . ?
N2 C10 C9 110.61(15) . . ?
N2 C10 H10A 109.5 . . ?
C9 C10 H10A 109.5 . . ?
N2 C10 H10B 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
N2 C11 C12 104.78(15) . . ?
N2 C11 H11A 127.6 . . ?
C12 C11 H11A 127.6 . . ?
N4 C12 C11 107.47(15) . . ?
N4 C12 C13 120.13(16) . . ?
C11 C12 C13 132.40(16) . . ?
C12 C13 C14 113.70(16) . . ?
C12 C13 H13A 108.8 . . ?
C14 C13 H13A 108.8 . . ?
C12 C13 H13B 108.8 . . ?
C14 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
O1 C14 C13 108.32(16) . . ?
O1 C14 H14A 110.0 . . ?
C13 C14 H14A 110.0 . . ?
O1 C14 H14B 110.0 . . ?
C13 C14 H14B 110.0 . . ?
H14A C14 H14B 108.4 . . ?
C14 O1 H1B 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 N2 N3 N4 -0.3(2) . . . . ?
C10 N2 N3 N4 174.87(15) . . . . ?
C11 N2 N3 Cu1 -165.21(12) . . . . ?
C10 N2 N3 Cu1 9.9(2) . . . . ?
N2 N3 N4 C12 0.8(2) . . . . ?
Cu1 N3 N4 C12 163.72(13) . . . . ?
N2 N3 N4 Cu2 179.62(11) . . . . ?
Cu1 N3 N4 Cu2 -17.5(2) . . . . ?
C6 C1 C2 C3 1.8(3) . . . . ?
C1 C2 C3 C4 -1.9(4) . . . . ?
C2 C3 C4 C5 -0.6(3) . . . . ?
C3 C4 C5 C7 -175.5(2) . . . . ?
C3 C4 C5 C6 3.1(3) . . . . ?
C9 N1 C6 C1 -173.76(18) . . . . ?
Cu1 N1 C6 C1 24.4(2) . . . . ?
C9 N1 C6 C5 5.2(3) . . . . ?
Cu1 N1 C6 C5 -156.73(14) . . . . ?
C2 C1 C6 N1 179.70(19) . . . . ?
C2 C1 C6 C5 0.8(3) . . . . ?
C7 C5 C6 N1 -3.4(3) . . . . ?
C4 C5 C6 N1 177.91(18) . . . . ?
C7 C5 C6 C1 175.53(19) . . . . ?
C4 C5 C6 C1 -3.2(3) . . . . ?
C6 C5 C7 C8 -1.3(3) . . . . ?
C4 C5 C7 C8 177.3(2) . . . . ?
C5 C7 C8 C9 4.0(3) . . . . ?
C6 N1 C9 C8 -2.4(3) . . . . ?
Cu1 N1 C9 C8 159.78(15) . . . . ?
C6 N1 C9 C10 179.06(16) . . . . ?
Cu1 N1 C9 C10 -18.8(2) . . . . ?
C7 C8 C9 N1 -2.3(3) . . . . ?
C7 C8 C9 C10 176.27(18) . . . . ?
N3 N2 C10 C9 -65.8(2) . . . . ?
C11 N2 C10 C9 108.1(2) . . . . ?
N1 C9 C10 N2 72.1(2) . . . . ?
C8 C9 C10 N2 -106.57(19) . . . . ?
N3 N2 C11 C12 -0.3(2) . . . . ?
C10 N2 C11 C12 -174.56(18) . . . . ?
N3 N4 C12 C11 -1.0(2) . . . . ?
Cu2 N4 C12 C11 -179.50(14) . . . . ?
N3 N4 C12 C13 178.25(16) . . . . ?
Cu2 N4 C12 C13 -0.2(3) . . . . ?
N2 C11 C12 N4 0.8(2) . . . . ?
N2 C11 C12 C13 -178.34(19) . . . . ?
N4 C12 C13 C14 -79.8(2) . . . . ?
C11 C12 C13 C14 99.2(2) . . . . ?
C12 C13 C14 O1 -75.3(2) . . . . ?

_refine_diff_density_max         1.691
_refine_diff_density_min         -1.508
_refine_diff_density_rms         0.143

_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_7
_database_code_depnum_ccdc_archive 'CCDC 1036544'
_audit_update_record             
;
2014-11-27 deposited with the CCDC.
2015-02-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H16 Cu2 I2 N4 O'
_chemical_formula_weight         649.20

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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                   44.1285(14)
_cell_length_b                   4.23210(10)
_cell_length_c                   19.1234(6)
_cell_angle_alpha                90
_cell_angle_beta                 99.0770(10)
_cell_angle_gamma                90
_cell_volume                     3526.69(18)
_cell_formula_units_Z            8
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    9914
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      30.44

_exptl_crystal_description       PLATE
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.445
_exptl_crystal_F_000             2448
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    5.924
_shelx_estimated_absorpt_T_min   0.343
_shelx_estimated_absorpt_T_max   0.756
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5222
_exptl_absorpt_correction_T_max  0.7461
_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            40833
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_limit_h_min       -62
_diffrn_reflns_limit_h_max       62
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.869
_diffrn_reflns_theta_max         30.528
_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             5350
_reflns_number_gt                4831
_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)+(0.0166P)²+9.9182P] 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         5350
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0262
_refine_ls_R_factor_gt           0.0221
_refine_ls_wR_factor_ref         0.0474
_refine_ls_wR_factor_gt          0.0461
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.15378(2) 0.72380(7) 0.46036(2) 0.01461(6) Uani 1 1 d . . . . .
Cu2 Cu 0.09977(2) 0.27063(7) 0.33931(2) 0.01740(6) Uani 1 1 d . . . . .
I1 I 0.16279(2) 0.20899(3) 0.38690(2) 0.01238(4) Uani 1 1 d . . . . .
I2 I 0.08322(2) -0.20938(3) 0.26201(2) 0.01502(4) Uani 1 1 d . . . . .
N1 N 0.16673(4) 0.6832(4) 0.56958(10) 0.0141(4) Uani 1 1 d . . . . .
N2 N 0.09727(4) 0.6874(4) 0.52808(10) 0.0136(4) Uani 1 1 d . . . . .
N3 N 0.10861(4) 0.6108(5) 0.46961(9) 0.0129(3) Uani 1 1 d . . . . .
N4 N 0.08879(4) 0.4159(4) 0.43300(9) 0.0131(3) Uani 1 1 d . . . . .
C1 C 0.21782(5) 0.5206(6) 0.55683(12) 0.0190(5) Uani 1 1 d . . . . .
H1A H 0.2153 0.6123 0.5109 0.023 Uiso 1 1 calc R U . . .
C2 C 0.24492(6) 0.3765(7) 0.58388(13) 0.0242(5) Uani 1 1 d . . . . .
H2A H 0.2614 0.3776 0.5575 0.029 Uiso 1 1 calc R U . . .
C3 C 0.24860(6) 0.2261(6) 0.65064(14) 0.0248(5) Uani 1 1 d . . . . .
H3A H 0.2672 0.1187 0.6678 0.030 Uiso 1 1 calc R U . . .
C4 C 0.22551(6) 0.2346(6) 0.69051(13) 0.0225(5) Uani 1 1 d . . . . .
H4A H 0.2281 0.1320 0.7352 0.027 Uiso 1 1 calc R U . . .
C5 C 0.19764(5) 0.3957(6) 0.66568(11) 0.0167(4) Uani 1 1 d . . . . .
C6 C 0.19356(5) 0.5332(5) 0.59707(11) 0.0144(4) Uani 1 1 d . . . . .
C7 C 0.17417(6) 0.4295(6) 0.70678(12) 0.0196(5) Uani 1 1 d . . . . .
H7A H 0.1761 0.3357 0.7524 0.024 Uiso 1 1 calc R U . . .
C8 C 0.14854(5) 0.5989(6) 0.68045(11) 0.0170(4) Uani 1 1 d . . . . .
H8A H 0.1330 0.6355 0.7086 0.020 Uiso 1 1 calc R U . . .
C9 C 0.14551(5) 0.7184(5) 0.61107(12) 0.0141(4) Uani 1 1 d . . . . .
C10 C 0.11642(5) 0.8896(6) 0.57996(11) 0.0160(4) Uani 1 1 d . . . . .
H10A H 0.1048 0.9480 0.6183 0.019 Uiso 1 1 calc R U . . .
H10B H 0.1217 1.0863 0.5566 0.019 Uiso 1 1 calc R U . . .
C11 C 0.07000(5) 0.5448(6) 0.52953(11) 0.0151(4) Uani 1 1 d . . . . .
H11A H 0.0574 0.5607 0.5653 0.018 Uiso 1 1 calc R U . . .
C12 C 0.06450(5) 0.3712(5) 0.46781(11) 0.0137(4) Uani 1 1 d . . . . .
C13 C 0.03758(5) 0.1785(6) 0.43584(12) 0.0161(4) Uani 1 1 d . . . . .
H13A H 0.0263 0.1050 0.4736 0.019 Uiso 1 1 calc R U . . .
H13B H 0.0448 -0.0099 0.4125 0.019 Uiso 1 1 calc R U . . .
C14 C 0.01590(5) 0.3728(6) 0.38109(13) 0.0195(5) Uani 1 1 d . . . . .
H14A H 0.0060 0.5388 0.4062 0.023 Uiso 1 1 calc R U . . .
H14B H 0.0282 0.4794 0.3490 0.023 Uiso 1 1 calc R U . . .
C15 C -0.00878(6) 0.1788(6) 0.33726(12) 0.0198(5) Uani 1 1 d . . . . .
H15A H -0.0207 0.3130 0.3003 0.024 Uiso 1 1 calc R U . . .
H15B H 0.0007 0.0049 0.3136 0.024 Uiso 1 1 calc R U . . .
O1 O -0.02873(4) 0.0515(5) 0.38239(9) 0.0230(4) Uani 1 1 d . . . . .
H1B H -0.0423 -0.0593 0.3583 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
Cu1 N1 2.0837(18) . ?
Cu1 N3 2.0841(19) . ?
Cu1 I1 2.5543(3) 1_565 ?
Cu1 I1 2.6561(3) . ?
Cu2 N4 2.0240(18) . ?
Cu2 I2 2.5503(3) . ?
Cu2 I2 2.6870(3) 1_565 ?
Cu2 I1 2.7986(3) . ?
I1 Cu1 2.5542(3) 1_545 ?
I2 Cu2 2.6870(3) 1_545 ?
N1 C9 1.328(3) . ?
N1 C6 1.373(3) . ?
N2 N3 1.335(2) . ?
N2 C11 1.350(3) . ?
N2 C10 1.472(3) . ?
N3 N4 1.320(2) . ?
N4 C12 1.361(3) . ?
C1 C2 1.369(3) . ?
C1 C6 1.414(3) . ?
C1 H1A 0.9500 . ?
C2 C3 1.413(4) . ?
C2 H2A 0.9500 . ?
C3 C4 1.366(4) . ?
C3 H3A 0.9500 . ?
C4 C5 1.421(3) . ?
C4 H4A 0.9500 . ?
C5 C7 1.403(3) . ?
C5 C6 1.421(3) . ?
C7 C8 1.366(3) . ?
C7 H7A 0.9500 . ?
C8 C9 1.406(3) . ?
C8 H8A 0.9500 . ?
C9 C10 1.512(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.379(3) . ?
C11 H11A 0.9500 . ?
C12 C13 1.491(3) . ?
C13 C14 1.540(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.508(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 O1 1.432(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
O1 H1B 0.8400 . ?

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
N1 Cu1 N3 90.62(7) . . ?
N1 Cu1 I1 125.15(5) . 1_565 ?
N3 Cu1 I1 117.72(5) . 1_565 ?
N1 Cu1 I1 114.97(5) . . ?
N3 Cu1 I1 94.68(5) . . ?
I1 Cu1 I1 108.617(11) 1_565 . ?
N4 Cu2 I2 131.94(6) . . ?
N4 Cu2 I2 98.97(5) . 1_565 ?
I2 Cu2 I2 107.786(11) . 1_565 ?
N4 Cu2 I1 96.01(5) . . ?
I2 Cu2 I1 107.045(11) . . ?
I2 Cu2 I1 115.154(12) 1_565 . ?
Cu1 I1 Cu1 108.618(11) 1_545 . ?
Cu1 I1 Cu2 91.197(10) 1_545 . ?
Cu1 I1 Cu2 82.621(9) . . ?
Cu2 I2 Cu2 107.786(11) . 1_545 ?
C9 N1 C6 118.03(19) . . ?
C9 N1 Cu1 118.81(15) . . ?
C6 N1 Cu1 120.37(15) . . ?
N3 N2 C11 111.21(18) . . ?
N3 N2 C10 117.04(18) . . ?
C11 N2 C10 131.66(19) . . ?
N4 N3 N2 106.93(17) . . ?
N4 N3 Cu1 131.38(14) . . ?
N2 N3 Cu1 120.35(14) . . ?
N3 N4 C12 109.54(18) . . ?
N3 N4 Cu2 115.35(14) . . ?
C12 N4 Cu2 135.05(15) . . ?
C2 C1 C6 120.1(2) . . ?
C2 C1 H1A 119.9 . . ?
C6 C1 H1A 119.9 . . ?
C1 C2 C3 120.7(2) . . ?
C1 C2 H2A 119.6 . . ?
C3 C2 H2A 119.6 . . ?
C4 C3 C2 120.2(2) . . ?
C4 C3 H3A 119.9 . . ?
C2 C3 H3A 119.9 . . ?
C3 C4 C5 120.6(2) . . ?
C3 C4 H4A 119.7 . . ?
C5 C4 H4A 119.7 . . ?
C7 C5 C6 118.6(2) . . ?
C7 C5 C4 122.6(2) . . ?
C6 C5 C4 118.8(2) . . ?
N1 C6 C1 119.4(2) . . ?
N1 C6 C5 121.3(2) . . ?
C1 C6 C5 119.4(2) . . ?
C8 C7 C5 119.2(2) . . ?
C8 C7 H7A 120.4 . . ?
C5 C7 H7A 120.4 . . ?
C7 C8 C9 119.1(2) . . ?
C7 C8 H8A 120.5 . . ?
C9 C8 H8A 120.5 . . ?
N1 C9 C8 123.5(2) . . ?
N1 C9 C10 117.0(2) . . ?
C8 C9 C10 119.5(2) . . ?
N2 C10 C9 110.37(18) . . ?
N2 C10 H10A 109.6 . . ?
C9 C10 H10A 109.6 . . ?
N2 C10 H10B 109.6 . . ?
C9 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
N2 C11 C12 104.92(19) . . ?
N2 C11 H11A 127.5 . . ?
C12 C11 H11A 127.5 . . ?
N4 C12 C11 107.39(19) . . ?
N4 C12 C13 120.90(19) . . ?
C11 C12 C13 131.6(2) . . ?
C12 C13 C14 110.87(19) . . ?
C12 C13 H13A 109.5 . . ?
C14 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C14 C13 H13B 109.5 . . ?
H13A C13 H13B 108.1 . . ?
C15 C14 C13 113.8(2) . . ?
C15 C14 H14A 108.8 . . ?
C13 C14 H14A 108.8 . . ?
C15 C14 H14B 108.8 . . ?
C13 C14 H14B 108.8 . . ?
H14A C14 H14B 107.7 . . ?
O1 C15 C14 109.18(19) . . ?
O1 C15 H15A 109.8 . . ?
C14 C15 H15A 109.8 . . ?
O1 C15 H15B 109.8 . . ?
C14 C15 H15B 109.8 . . ?
H15A C15 H15B 108.3 . . ?
C15 O1 H1B 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 N2 N3 N4 -0.4(2) . . . . ?
C10 N2 N3 N4 176.38(18) . . . . ?
C11 N2 N3 Cu1 -168.63(15) . . . . ?
C10 N2 N3 Cu1 8.1(2) . . . . ?
N2 N3 N4 C12 0.8(2) . . . . ?
Cu1 N3 N4 C12 167.21(15) . . . . ?
N2 N3 N4 Cu2 178.26(13) . . . . ?
Cu1 N3 N4 Cu2 -15.3(2) . . . . ?
C6 C1 C2 C3 2.9(4) . . . . ?
C1 C2 C3 C4 -2.9(4) . . . . ?
C2 C3 C4 C5 -0.3(4) . . . . ?
C3 C4 C5 C7 -175.5(2) . . . . ?
C3 C4 C5 C6 3.3(4) . . . . ?
C9 N1 C6 C1 -173.6(2) . . . . ?
Cu1 N1 C6 C1 25.6(3) . . . . ?
C9 N1 C6 C5 5.2(3) . . . . ?
Cu1 N1 C6 C5 -155.66(17) . . . . ?
C2 C1 C6 N1 178.9(2) . . . . ?
C2 C1 C6 C5 0.1(4) . . . . ?
C7 C5 C6 N1 -3.2(3) . . . . ?
C4 C5 C6 N1 178.0(2) . . . . ?
C7 C5 C6 C1 175.6(2) . . . . ?
C4 C5 C6 C1 -3.2(3) . . . . ?
C6 C5 C7 C8 -1.5(3) . . . . ?
C4 C5 C7 C8 177.3(2) . . . . ?
C5 C7 C8 C9 3.9(4) . . . . ?
C6 N1 C9 C8 -2.7(3) . . . . ?
Cu1 N1 C9 C8 158.44(18) . . . . ?
C6 N1 C9 C10 178.91(19) . . . . ?
Cu1 N1 C9 C10 -19.9(3) . . . . ?
C7 C8 C9 N1 -1.9(4) . . . . ?
C7 C8 C9 C10 176.4(2) . . . . ?
N3 N2 C10 C9 -65.0(2) . . . . ?
C11 N2 C10 C9 111.0(3) . . . . ?
N1 C9 C10 N2 73.2(3) . . . . ?
C8 C9 C10 N2 -105.3(2) . . . . ?
N3 N2 C11 C12 -0.1(2) . . . . ?
C10 N2 C11 C12 -176.3(2) . . . . ?
N3 N4 C12 C11 -0.9(2) . . . . ?
Cu2 N4 C12 C11 -177.64(16) . . . . ?
N3 N4 C12 C13 175.76(19) . . . . ?
Cu2 N4 C12 C13 -1.0(3) . . . . ?
N2 C11 C12 N4 0.6(2) . . . . ?
N2 C11 C12 C13 -175.5(2) . . . . ?
N4 C12 C13 C14 -80.2(3) . . . . ?
C11 C12 C13 C14 95.5(3) . . . . ?
C12 C13 C14 C15 169.7(2) . . . . ?
C13 C14 C15 O1 64.8(3) . . . . ?

_refine_diff_density_max         0.829
_refine_diff_density_min         -0.727
_refine_diff_density_rms         0.115

_shelxl_version_number           2014-3

