# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_cs1-14d_e
_database_code_depnum_ccdc_archive 'CCDC 1888939'
loop_
_audit_author_name
_audit_author_address
'Simon J. Teat'
;Advanced Light Source
United States of America
;
_audit_update_record             
;
2019-01-05 deposited with the CCDC.	2019-04-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H16 Cu I N6'
_chemical_formula_weight         482.79

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0040 0.0020
'XDISP Program in WinGX S.Brennan & P.L.Cowan Rev.Sci.Instrum.63,850 1992'
H H 0.0000 0.0000
'XDISP Program in WinGX S.Brennan & P.L.Cowan Rev.Sci.Instrum.63,850 1992'
N N 0.0076 0.0040
'XDISP Program in WinGX S.Brennan & P.L.Cowan Rev.Sci.Instrum.63,850 1992'
Cu Cu 0.2913 1.4803
'XDISP Program in WinGX S.Brennan & P.L.Cowan Rev.Sci.Instrum.63,850 1992'
I I -0.3071 2.1212
'XDISP Program in WinGX S.Brennan & P.L.Cowan Rev.Sci.Instrum.63,850 1992'

_space_group_crystal_system      tetragonal
_space_group_IT_number           112
_space_group_name_H-M_alt        'P -4 2 c'
_space_group_name_Hall           'P -4 2c'

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

_cell_length_a                   13.8410(8)
_cell_length_b                   13.8410(8)
_cell_length_c                   8.7594(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1678.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9993
_cell_measurement_theta_min      3.0006
_cell_measurement_theta_max      32.0817

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.911
_exptl_crystal_F_000             944
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.010
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    3.951
_shelx_estimated_absorpt_T_min   0.315
_shelx_estimated_absorpt_T_max   0.962
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.729
_exptl_absorpt_correction_T_max  0.962
_exptl_absorpt_process_details   'SADABS 2016/2 Bruker AXS Madison WI USA'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.7749
_diffrn_radiation_type           synchrotron
_diffrn_source                   'Advanced Light Source station 11.3.1'
_diffrn_measurement_device_type  'Bruker D8 with PHOTONII detector'
_diffrn_measurement_method       'ω/θ shutterless scans'
_diffrn_detector_area_resol_mean 7.39
_diffrn_reflns_number            23851
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_av_R_equivalents  0.0595
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.604
_diffrn_reflns_theta_max         32.103
_diffrn_reflns_theta_full        27.706
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2273
_reflns_number_gt                2134
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.752
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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 APEX 3'
_computing_cell_refinement       'Bruker SAINT v8.38a'
_computing_data_reduction        'Bruker SAINT v8.38a'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL & local programs'
_refine_special_details          
;
 All non-hydrogen atoms were refined anisotropically. Hydrogen atoms
 were place geometrical, constrained and refined using a riding model.
 Geometrical and displacement parameter restraints were used to model
 the disodered CH2 chain.

 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+13.8473P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'Dual space'
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.45(7)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2273
_refine_ls_number_parameters     130
_refine_ls_number_restraints     26
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0458
_refine_ls_wR_factor_ref         0.1101
_refine_ls_wR_factor_gt          0.1091
_refine_ls_goodness_of_fit_ref   1.256
_refine_ls_restrained_S_all      1.253
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.500000 0.09760(9) 0.750000 0.0208(3) Uani 1 2 d S T P . .
I1 I 0.500000 0.000000 0.49188(7) 0.01954(18) Uani 1 2 d S T P . .
N1 N 0.6156(6) 0.1893(5) 0.7238(8) 0.0205(19) Uani 1 1 d . . . . .
N2 N 0.6091(7) 0.2710(6) 0.6502(10) 0.0274(18) Uani 1 1 d . . . . .
N3 N 0.6954(8) 0.3181(6) 0.6554(12) 0.037(2) Uani 1 1 d . . . . .
C1 C 0.7088(7) 0.1829(7) 0.7779(8) 0.021(2) Uani 1 1 d . . . . .
C2 C 0.7522(6) 0.1092(7) 0.8623(12) 0.025(2) Uani 1 1 d . . . . .
H2A H 0.717782 0.052373 0.889187 0.030 Uiso 1 1 calc R U . . .
C3 C 0.8474(8) 0.1223(10) 0.9051(16) 0.042(3) Uani 1 1 d . . . . .
H3A H 0.880240 0.075055 0.964248 0.050 Uiso 1 1 calc R U . . .
C4 C 0.8954(9) 0.2095(9) 0.8578(18) 0.048(3) Uani 1 1 d . . . . .
H4A H 0.961329 0.216872 0.885394 0.058 Uiso 1 1 calc R U . . .
C5 C 0.8540(8) 0.2816(8) 0.7773(17) 0.044(4) Uani 1 1 d . . . . .
H5A H 0.887168 0.339887 0.754294 0.053 Uiso 1 1 calc R U . . .
C6 C 0.7588(8) 0.2644(7) 0.730(2) 0.030(3) Uani 1 1 d . . . . .
C7 C 0.6850(17) 0.4137(16) 0.565(3) 0.026(4) Uani 0.5 1 d D . P . .
H7A H 0.745841 0.428699 0.510567 0.031 Uiso 0.5 1 calc R U P . .
H7B H 0.632395 0.408132 0.488845 0.031 Uiso 0.5 1 calc R U P . .
C8 C 0.6618(10) 0.4928(15) 0.6795(16) 0.018(3) Uani 0.5 1 d D . P . .
H8A H 0.648731 0.553792 0.624070 0.022 Uiso 0.5 1 calc R U P . .
H8B H 0.602744 0.475116 0.736644 0.022 Uiso 0.5 1 calc R U P . .
C9 C 0.7438(10) 0.5088(16) 0.7909(15) 0.024(4) Uani 0.5 1 d D . P . .
H9A H 0.770504 0.574951 0.799035 0.029 Uiso 0.5 1 calc R U P . .
H9B H 0.781192 0.464935 0.857947 0.029 Uiso 0.5 1 calc R U P . .
C10 C 0.7207(16) 0.5880(14) 0.905(2) 0.020(4) Uani 0.5 1 d D . P . .
H10A H 0.666563 0.565488 0.969939 0.024 Uiso 0.5 1 calc R U P . .
H10B H 0.777551 0.596220 0.972754 0.024 Uiso 0.5 1 calc R U P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N1 2.055(7) . ?
Cu1 N1 2.055(7) 5_656 ?
Cu1 I1 2.6338(8) . ?
Cu1 I1 2.6338(8) 5_656 ?
Cu1 Cu1 2.702(3) 2_655 ?
N1 N2 1.305(10) . ?
N1 C1 1.377(12) . ?
N2 N3 1.361(13) . ?
N3 C6 1.323(17) . ?
N3 C10 1.45(2) 6_566 ?
N3 C7 1.55(3) . ?
C1 C6 1.389(13) . ?
C1 C2 1.396(13) . ?
C2 C3 1.381(14) . ?
C2 H2A 0.9500 . ?
C3 C4 1.438(18) . ?
C3 H3A 0.9500 . ?
C4 C5 1.35(2) . ?
C4 H4A 0.9500 . ?
C5 C6 1.402(16) . ?
C5 H5A 0.9500 . ?
C7 C8 1.519(15) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.513(14) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C9 0.76(2) 6_566 ?
C9 C10 1.520(15) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Cu1 N1 103.7(5) . 5_656 ?
N1 Cu1 I1 102.8(2) . . ?
N1 Cu1 I1 114.4(2) 5_656 . ?
N1 Cu1 I1 114.4(2) . 5_656 ?
N1 Cu1 I1 102.8(2) 5_656 5_656 ?
I1 Cu1 I1 118.29(5) . 5_656 ?
N1 Cu1 Cu1 128.1(2) . 2_655 ?
N1 Cu1 Cu1 128.1(2) 5_656 2_655 ?
I1 Cu1 Cu1 59.14(2) . 2_655 ?
I1 Cu1 Cu1 59.14(2) 5_656 2_655 ?
Cu1 I1 Cu1 61.71(5) . 2_655 ?
N2 N1 C1 106.9(7) . . ?
N2 N1 Cu1 122.5(7) . . ?
C1 N1 Cu1 130.6(6) . . ?
N1 N2 N3 109.7(9) . . ?
C6 N3 N2 109.3(9) . . ?
C6 N3 C10 121.7(12) . 6_566 ?
N2 N3 C10 129.1(13) . 6_566 ?
C6 N3 C7 142.6(12) . . ?
N2 N3 C7 108.1(12) . . ?
C10 N3 C7 21.2(9) 6_566 . ?
N1 C1 C6 108.1(9) . . ?
N1 C1 C2 129.3(8) . . ?
C6 C1 C2 122.6(9) . . ?
C3 C2 C1 117.3(10) . . ?
C3 C2 H2A 121.3 . . ?
C1 C2 H2A 121.3 . . ?
C2 C3 C4 118.1(13) . . ?
C2 C3 H3A 120.9 . . ?
C4 C3 H3A 120.9 . . ?
C5 C4 C3 125.1(12) . . ?
C5 C4 H4A 117.4 . . ?
C3 C4 H4A 117.4 . . ?
C4 C5 C6 115.3(10) . . ?
C4 C5 H5A 122.3 . . ?
C6 C5 H5A 122.3 . . ?
N3 C6 C1 106.0(9) . . ?
N3 C6 C5 132.4(10) . . ?
C1 C6 C5 121.1(12) . . ?
C8 C7 N3 107.3(17) . . ?
C8 C7 H7A 110.2 . . ?
N3 C7 H7A 110.2 . . ?
C8 C7 H7B 110.2 . . ?
N3 C7 H7B 110.2 . . ?
H7A C7 H7B 108.5 . . ?
C9 C8 C7 111.9(13) . . ?
C9 C8 H8A 109.2 . . ?
C7 C8 H8A 109.2 . . ?
C9 C8 H8B 109.2 . . ?
C7 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
C9 C9 C8 101.8(12) 6_566 6_566 ?
C9 C9 C8 48.9(8) 6_566 . ?
C8 C9 C8 53.8(14) 6_566 . ?
C9 C9 C10 149(4) 6_566 . ?
C8 C9 C10 70.2(16) 6_566 . ?
C8 C9 C10 111.9(13) . . ?
C9 C9 C7 147(3) 6_566 6_566 ?
C8 C9 C7 55.1(10) 6_566 6_566 ?
C8 C9 C7 101.2(13) . 6_566 ?
C10 C9 C7 15.6(10) . 6_566 ?
C9 C9 H9A 111.4 6_566 . ?
C8 C9 H9A 111.4 6_566 . ?
C8 C9 H9A 117.4 . . ?
C10 C9 H9A 50.5 . . ?
C7 C9 H9A 65.0 6_566 . ?
C9 C9 H9B 111.4 6_566 . ?
C8 C9 H9B 111.4 6_566 . ?
C8 C9 H9B 133.2 . . ?
C10 C9 H9B 99.3 . . ?
C7 C9 H9B 100.4 6_566 . ?
H9A C9 H9B 109.3 . . ?
N3 C10 C9 117.2(16) 6_566 . ?
N3 C10 H10A 108.0 6_566 . ?
C9 C10 H10A 108.0 . . ?
N3 C10 H10B 108.0 6_566 . ?
C9 C10 H10B 108.0 . . ?
H10A C10 H10B 107.2 . . ?
N3 C10 H7A 132(3) 6_566 6_566 ?
C9 C10 H7A 107(2) . 6_566 ?
H10A C10 H7A 74.2 . 6_566 ?
H10B C10 H7A 35.5 . 6_566 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 N2 N3 -0.2(10) . . . . ?
Cu1 N1 N2 N3 177.9(6) . . . . ?
N1 N2 N3 C6 1.7(13) . . . . ?
N1 N2 N3 C10 -177.6(13) . . . 6_566 ?
N1 N2 N3 C7 179.2(10) . . . . ?
N2 N1 C1 C6 -1.3(11) . . . . ?
Cu1 N1 C1 C6 -179.2(8) . . . . ?
N2 N1 C1 C2 -179.4(9) . . . . ?
Cu1 N1 C1 C2 2.7(13) . . . . ?
N1 C1 C2 C3 -178.6(9) . . . . ?
C6 C1 C2 C3 3.5(16) . . . . ?
C1 C2 C3 C4 -1.1(16) . . . . ?
C2 C3 C4 C5 2(2) . . . . ?
C3 C4 C5 C6 -4(2) . . . . ?
N2 N3 C6 C1 -2.4(14) . . . . ?
C10 N3 C6 C1 176.9(12) 6_566 . . . ?
C7 N3 C6 C1 -178.5(16) . . . . ?
N2 N3 C6 C5 -174.3(16) . . . . ?
C10 N3 C6 C5 5(3) 6_566 . . . ?
C7 N3 C6 C5 10(3) . . . . ?
N1 C1 C6 N3 2.3(14) . . . . ?
C2 C1 C6 N3 -179.4(10) . . . . ?
N1 C1 C6 C5 175.3(12) . . . . ?
C2 C1 C6 C5 -6.4(19) . . . . ?
C4 C5 C6 N3 177.4(16) . . . . ?
C4 C5 C6 C1 6(2) . . . . ?
C6 N3 C7 C8 -88(2) . . . . ?
N2 N3 C7 C8 95.7(14) . . . . ?
C10 N3 C7 C8 -77(3) 6_566 . . . ?
N3 C7 C8 C9 64(2) . . . . ?
C7 C8 C9 C9 29(4) . . . 6_566 ?
C7 C8 C9 C8 -138(3) . . . 6_566 ?
C7 C8 C9 C10 180(2) . . . . ?
C7 C8 C9 C7 -168.2(13) . . . 6_566 ?
C9 C9 C10 N3 -11(5) 6_566 . . 6_566 ?
C8 C9 C10 N3 -91(2) 6_566 . . 6_566 ?
C8 C9 C10 N3 -56(2) . . . 6_566 ?
C7 C9 C10 N3 -105(6) 6_566 . . 6_566 ?

_refine_diff_density_max         0.683
_refine_diff_density_min         -1.714
_refine_diff_density_rms         0.168

####################################################################### 
# 
# 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_twin5
_database_code_depnum_ccdc_archive 'CCDC 1888940'
loop_
_audit_author_name
_audit_author_address
'Simon J. Teat'
;Advanced Light Source
United States of America
;
_audit_update_record             
;
2019-01-05 deposited with the CCDC.	2019-04-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H27 Cu3 I3 N6'
_chemical_formula_weight         898.77

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0040 0.0020
'XDISP Program in WinGX S.Brennan & P.L.Cowan Rev.Sci.Instrum.63,850 1992'
H H 0.0000 0.0000
'XDISP Program in WinGX S.Brennan & P.L.Cowan Rev.Sci.Instrum.63,850 1992'
N N 0.0076 0.0040
'XDISP Program in WinGX S.Brennan & P.L.Cowan Rev.Sci.Instrum.63,850 1992'
Cu Cu 0.2913 1.4803
'XDISP Program in WinGX S.Brennan & P.L.Cowan Rev.Sci.Instrum.63,850 1992'
I I -0.3071 2.1212
'XDISP Program in WinGX S.Brennan & P.L.Cowan Rev.Sci.Instrum.63,850 1992'

_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                   10.2612(5)
_cell_length_b                   10.7326(6)
_cell_length_c                   11.8422(7)
_cell_angle_alpha                106.811(3)
_cell_angle_beta                 90.123(3)
_cell_angle_gamma                101.770(3)
_cell_volume                     1219.58(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9857
_cell_measurement_theta_min      2.4857
_cell_measurement_theta_max      33.6651

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.447
_exptl_crystal_F_000             846
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.060
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    8.038
_shelx_estimated_absorpt_T_min   0.644
_shelx_estimated_absorpt_T_max   0.856
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.712
_exptl_absorpt_correction_T_max  0.856
_exptl_absorpt_process_details   'SADABS 2016/2 Bruker AXS Madison WI USA'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.7749
_diffrn_radiation_type           synchrotron
_diffrn_source                   'Advanced Light Source station 11.3.1'
_diffrn_measurement_device_type  'Bruker D8 with PHOTON 100 detector'
_diffrn_measurement_method       'ω/θ shutterless scans'
_diffrn_detector_area_resol_mean 10.42
_diffrn_reflns_number            37159
_diffrn_reflns_av_unetI/netI     0.0391
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.486
_diffrn_reflns_theta_max         33.676
_diffrn_reflns_theta_full        27.706
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             7336
_reflns_number_gt                6378
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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 APEX 3'
_computing_cell_refinement       'Bruker SAINT v8.38a'
_computing_data_reduction        'Bruker SAINT v8.38a'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL & local programs'
_refine_special_details          
;
 Several crystals were tried and this was the best crystal. The diffraction
 pattern showed twinning. Using Cell_now two orientation matices were
 determined, the relationship between these components was determined to be
 180 degrees about reciprocal axis -1 1 0.  The data were integrated using the
 two matrices in SAINT, TWINABS was used to produce a merged HKLF4 file,
 for structure solution and initial refinement, and HKLF5 file for final
 structure refinement. The HKLF5 file contained the merged reflections first
 component and those that overlapped with this component, which were split
 into 2 reflection. TWINABS indicated the twin faction to be 58:42 The structure
 was solved using the HKLF4 file, but the best refinement was given by the
 HKLF5 file. The refinement also get the ratio to be 58:42.
 All non-hydrogen atoms were refined anisotropically.
 Hydrogen atoms were placed geometrically and refined using a riding model.

 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0226P)²+2.3172P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7336
_refine_ls_number_parameters     275
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0310
_refine_ls_wR_factor_ref         0.0635
_refine_ls_wR_factor_gt          0.0602
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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 0.70560(5) 0.40171(5) 0.20542(5) 0.01467(10) Uani 1 1 d . . . . .
Cu2 Cu 0.91797(5) 0.51172(5) 0.39694(5) 0.01689(11) Uani 1 1 d . . . . .
Cu3 Cu 0.83484(5) 0.24341(5) 0.26338(5) 0.01515(10) Uani 1 1 d . . . . .
I1 I 0.96149(2) 0.43896(3) 0.16782(2) 0.01277(5) Uani 1 1 d . . . . .
I2 I 0.57537(2) 0.16647(3) 0.18701(3) 0.01625(6) Uani 1 1 d . . . . .
I3 I 0.84838(3) 0.32099(3) 0.49813(2) 0.01393(6) Uani 1 1 d . . . . .
C1 C 0.4892(4) 0.5430(4) 0.1730(4) 0.0120(7) Uani 1 1 d . . . . .
N1 N 0.6170(3) 0.5335(3) 0.1684(3) 0.0121(6) Uani 1 1 d . . . . .
C2 C 0.6785(4) 0.6249(4) 0.1131(4) 0.0164(8) Uani 1 1 d . . . . .
H2 H 0.770319 0.640734 0.097742 0.020 Uiso 1 1 calc R U . . .
C3 C 0.5876(4) 0.6889(4) 0.0839(4) 0.0162(8) Uani 1 1 d . . . . .
H3 H 0.603495 0.756731 0.045813 0.019 Uiso 1 1 calc R U . . .
N2 N 0.4676(3) 0.6349(3) 0.1212(3) 0.0141(7) Uani 1 1 d . . . . .
C4 C 0.3830(4) 0.4649(4) 0.2250(4) 0.0185(9) Uani 1 1 d . . . . .
H4A H 0.419522 0.400548 0.252581 0.028 Uiso 1 1 calc R U . . .
H4B H 0.309874 0.417268 0.164912 0.028 Uiso 1 1 calc R U . . .
H4C H 0.349274 0.525221 0.291729 0.028 Uiso 1 1 calc R U . . .
C5 C 0.3420(4) 0.6769(4) 0.1102(4) 0.0147(8) Uani 1 1 d . . . . .
H5A H 0.265880 0.601438 0.104680 0.018 Uiso 1 1 calc R U . . .
H5B H 0.338393 0.703508 0.037129 0.018 Uiso 1 1 calc R U . . .
C6 C 0.3310(4) 0.7934(4) 0.2168(4) 0.0168(8) Uani 1 1 d . . . . .
H6A H 0.404104 0.870229 0.218658 0.020 Uiso 1 1 calc R U . . .
H6B H 0.342269 0.768383 0.289813 0.020 Uiso 1 1 calc R U . . .
C7 C 0.1974(4) 0.8355(4) 0.2152(4) 0.0168(8) Uani 1 1 d . . . . .
H7A H 0.124444 0.755352 0.200125 0.020 Uiso 1 1 calc R U . . .
H7B H 0.187457 0.895616 0.294219 0.020 Uiso 1 1 calc R U . . .
C8 C 0.1826(4) 0.9059(4) 0.1227(4) 0.0142(8) Uani 1 1 d . . . . .
H8A H 0.259875 0.981215 0.132462 0.017 Uiso 1 1 calc R U . . .
H8B H 0.182405 0.842972 0.042803 0.017 Uiso 1 1 calc R U . . .
N3 N 0.0595(3) 0.9558(3) 0.1327(3) 0.0128(6) Uani 1 1 d . . . . .
C9 C 0.0414(4) 1.0736(4) 0.2033(4) 0.0133(8) Uani 1 1 d . . . . .
N4 N -0.0839(3) 1.0861(3) 0.1914(3) 0.0136(7) Uani 1 1 d . . . . .
C10 C -0.1490(4) 0.9690(4) 0.1091(4) 0.0137(8) Uani 1 1 d . . . . .
H10 H -0.240391 0.948588 0.082461 0.016 Uiso 1 1 calc R U . . .
C11 C -0.0615(4) 0.8877(4) 0.0722(4) 0.0136(8) Uani 1 1 d . . . . .
H11 H -0.079926 0.801645 0.016210 0.016 Uiso 1 1 calc R U . . .
C12 C 0.1493(4) 1.1766(4) 0.2817(4) 0.0183(9) Uani 1 1 d . . . . .
H12A H 0.114622 1.255852 0.320639 0.028 Uiso 1 1 calc R U . . .
H12B H 0.223305 1.200550 0.234509 0.028 Uiso 1 1 calc R U . . .
H12C H 0.181121 1.141194 0.341670 0.028 Uiso 1 1 calc R U . . .
N5 N 0.7799(3) 0.6235(3) 0.4293(3) 0.0130(6) Uani 1 1 d . . . . .
C13 C 0.7808(4) 0.7391(4) 0.4096(4) 0.0143(8) Uani 1 1 d . . . . .
N6 N 0.6675(3) 0.7812(3) 0.4452(3) 0.0129(7) Uani 1 1 d . . . . .
C14 C 0.6609(4) 0.5901(4) 0.4785(4) 0.0151(8) Uani 1 1 d . . . . .
H14 H 0.632401 0.511272 0.500977 0.018 Uiso 1 1 calc R U . . .
C15 C 0.5911(4) 0.6866(4) 0.4900(4) 0.0164(8) Uani 1 1 d . . . . .
H15 H 0.506632 0.689047 0.522206 0.020 Uiso 1 1 calc R U . . .
C16 C 0.8892(4) 0.8165(4) 0.3594(4) 0.0184(9) Uani 1 1 d . . . . .
H16A H 0.939220 0.891948 0.422810 0.028 Uiso 1 1 calc R U . . .
H16B H 0.850692 0.849743 0.300956 0.028 Uiso 1 1 calc R U . . .
H16C H 0.949284 0.759117 0.321104 0.028 Uiso 1 1 calc R U . . .
C17 C 0.6325(4) 0.9023(4) 0.4342(4) 0.0166(8) Uani 1 1 d . . . . .
H17A H 0.609167 0.890479 0.350028 0.020 Uiso 1 1 calc R U . . .
H17B H 0.710908 0.977172 0.460565 0.020 Uiso 1 1 calc R U . . .
C18 C 0.5172(4) 0.9365(4) 0.5061(4) 0.0160(8) Uani 1 1 d . . . . .
H18A H 0.540129 0.948134 0.590294 0.019 Uiso 1 1 calc R U . . .
H18B H 0.438366 0.862103 0.479433 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 1.975(3) . ?
Cu1 I2 2.5519(6) . ?
Cu1 Cu3 2.5896(7) . ?
Cu1 I1 2.6328(6) . ?
Cu1 Cu2 2.9440(8) . ?
Cu2 N5 2.006(3) . ?
Cu2 I3 2.6387(6) . ?
Cu2 I1 2.6633(6) . ?
Cu2 I3 2.7306(6) 2_766 ?
Cu2 Cu3 2.8070(8) . ?
Cu3 N4 2.005(3) 1_645 ?
Cu3 I3 2.6558(6) . ?
Cu3 I2 2.6925(6) . ?
Cu3 I1 2.7643(6) . ?
C1 N1 1.336(5) . ?
C1 N2 1.356(5) . ?
C1 C4 1.482(6) . ?
N1 C2 1.382(5) . ?
C2 C3 1.364(6) . ?
C2 H2 0.9500 . ?
C3 N2 1.380(5) . ?
C3 H3 0.9500 . ?
N2 C5 1.467(5) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.522(6) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.529(6) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.523(6) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 N3 1.461(5) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
N3 C9 1.348(5) . ?
N3 C11 1.383(5) . ?
C9 N4 1.331(5) . ?
C9 C12 1.487(6) . ?
N4 C10 1.386(5) . ?
C10 C11 1.363(5) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
N5 C13 1.325(5) . ?
N5 C14 1.380(5) . ?
C13 N6 1.357(5) . ?
C13 C16 1.481(6) . ?
N6 C15 1.383(5) . ?
N6 C17 1.457(5) . ?
C14 C15 1.351(6) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.504(5) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C18 1.521(8) 2_676 ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Cu1 I2 120.75(10) . . ?
N1 Cu1 Cu3 175.79(10) . . ?
I2 Cu1 Cu3 63.154(18) . . ?
N1 Cu1 I1 113.52(10) . . ?
I2 Cu1 I1 119.02(2) . . ?
Cu3 Cu1 I1 63.911(17) . . ?
N1 Cu1 Cu2 115.31(10) . . ?
I2 Cu1 Cu2 115.26(2) . . ?
Cu3 Cu1 Cu2 60.562(19) . . ?
I1 Cu1 Cu2 56.723(15) . . ?
N5 Cu2 I3 107.46(10) . . ?
N5 Cu2 I1 111.11(10) . . ?
I3 Cu2 I1 117.45(2) . . ?
N5 Cu2 I3 105.49(10) . 2_766 ?
I3 Cu2 I3 110.53(2) . 2_766 ?
I1 Cu2 I3 104.188(19) . 2_766 ?
N5 Cu2 Cu3 117.64(10) . . ?
I3 Cu2 Cu3 58.279(17) . . ?
I1 Cu2 Cu3 60.639(17) . . ?
I3 Cu2 Cu3 136.86(2) 2_766 . ?
N5 Cu2 Cu1 71.16(10) . . ?
I3 Cu2 Cu1 95.60(2) . . ?
I1 Cu2 Cu1 55.738(16) . . ?
I3 Cu2 Cu1 153.08(2) 2_766 . ?
Cu3 Cu2 Cu1 53.461(18) . . ?
N4 Cu3 Cu1 141.35(10) 1_645 . ?
N4 Cu3 I3 114.34(10) 1_645 . ?
Cu1 Cu3 I3 104.25(2) . . ?
N4 Cu3 I2 105.92(10) 1_645 . ?
Cu1 Cu3 I2 57.738(17) . . ?
I3 Cu3 I2 107.90(2) . . ?
N4 Cu3 I1 105.03(10) 1_645 . ?
Cu1 Cu3 I1 58.804(17) . . ?
I3 Cu3 I1 113.44(2) . . ?
I2 Cu3 I1 109.92(2) . . ?
N4 Cu3 Cu2 138.50(10) 1_645 . ?
Cu1 Cu3 Cu2 65.98(2) . . ?
I3 Cu3 Cu2 57.687(17) . . ?
I2 Cu3 Cu2 115.30(2) . . ?
I1 Cu3 Cu2 57.108(17) . . ?
Cu1 I1 Cu2 67.539(18) . . ?
Cu1 I1 Cu3 57.284(16) . . ?
Cu2 I1 Cu3 62.253(17) . . ?
Cu1 I2 Cu3 59.107(17) . . ?
Cu2 I3 Cu3 64.034(18) . . ?
Cu2 I3 Cu2 69.47(2) . 2_766 ?
Cu3 I3 Cu2 115.017(19) . 2_766 ?
N1 C1 N2 110.2(3) . . ?
N1 C1 C4 126.3(4) . . ?
N2 C1 C4 123.4(3) . . ?
C1 N1 C2 106.1(3) . . ?
C1 N1 Cu1 130.1(3) . . ?
C2 N1 Cu1 123.1(3) . . ?
C3 C2 N1 109.7(4) . . ?
C3 C2 H2 125.1 . . ?
N1 C2 H2 125.1 . . ?
C2 C3 N2 105.9(4) . . ?
C2 C3 H3 127.1 . . ?
N2 C3 H3 127.1 . . ?
C1 N2 C3 108.0(3) . . ?
C1 N2 C5 127.2(4) . . ?
C3 N2 C5 124.7(4) . . ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N2 C5 C6 110.2(3) . . ?
N2 C5 H5A 109.6 . . ?
C6 C5 H5A 109.6 . . ?
N2 C5 H5B 109.6 . . ?
C6 C5 H5B 109.6 . . ?
H5A C5 H5B 108.1 . . ?
C5 C6 C7 112.8(3) . . ?
C5 C6 H6A 109.0 . . ?
C7 C6 H6A 109.0 . . ?
C5 C6 H6B 109.0 . . ?
C7 C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?
C8 C7 C6 113.8(3) . . ?
C8 C7 H7A 108.8 . . ?
C6 C7 H7A 108.8 . . ?
C8 C7 H7B 108.8 . . ?
C6 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
N3 C8 C7 111.6(3) . . ?
N3 C8 H8A 109.3 . . ?
C7 C8 H8A 109.3 . . ?
N3 C8 H8B 109.3 . . ?
C7 C8 H8B 109.3 . . ?
H8A C8 H8B 108.0 . . ?
C9 N3 C11 107.5(3) . . ?
C9 N3 C8 127.0(3) . . ?
C11 N3 C8 125.5(3) . . ?
N4 C9 N3 111.2(4) . . ?
N4 C9 C12 125.0(4) . . ?
N3 C9 C12 123.8(4) . . ?
C9 N4 C10 105.7(3) . . ?
C9 N4 Cu3 129.1(3) . 1_465 ?
C10 N4 Cu3 125.0(3) . 1_465 ?
C11 C10 N4 109.5(3) . . ?
C11 C10 H10 125.3 . . ?
N4 C10 H10 125.3 . . ?
C10 C11 N3 106.1(3) . . ?
C10 C11 H11 126.9 . . ?
N3 C11 H11 126.9 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C13 N5 C14 106.4(3) . . ?
C13 N5 Cu2 129.4(3) . . ?
C14 N5 Cu2 124.3(3) . . ?
N5 C13 N6 110.3(4) . . ?
N5 C13 C16 126.5(4) . . ?
N6 C13 C16 123.2(4) . . ?
C13 N6 C15 107.5(3) . . ?
C13 N6 C17 125.5(3) . . ?
C15 N6 C17 126.9(3) . . ?
C15 C14 N5 109.7(4) . . ?
C15 C14 H14 125.2 . . ?
N5 C14 H14 125.2 . . ?
C14 C15 N6 106.1(4) . . ?
C14 C15 H15 126.9 . . ?
N6 C15 H15 126.9 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N6 C17 C18 112.1(3) . . ?
N6 C17 H17A 109.2 . . ?
C18 C17 H17A 109.2 . . ?
N6 C17 H17B 109.2 . . ?
C18 C17 H17B 109.2 . . ?
H17A C17 H17B 107.9 . . ?
C17 C18 C18 111.2(4) . 2_676 ?
C17 C18 H18A 109.4 . . ?
C18 C18 H18A 109.4 2_676 . ?
C17 C18 H18B 109.4 . . ?
C18 C18 H18B 109.4 2_676 . ?
H18A C18 H18B 108.0 . . ?

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
N2 C1 N1 C2 1.0(5) . . . . ?
C4 C1 N1 C2 -179.8(4) . . . . ?
N2 C1 N1 Cu1 -169.7(3) . . . . ?
C4 C1 N1 Cu1 9.6(6) . . . . ?
C1 N1 C2 C3 -0.3(5) . . . . ?
Cu1 N1 C2 C3 171.2(3) . . . . ?
N1 C2 C3 N2 -0.5(5) . . . . ?
N1 C1 N2 C3 -1.3(5) . . . . ?
C4 C1 N2 C3 179.4(4) . . . . ?
N1 C1 N2 C5 -178.6(4) . . . . ?
C4 C1 N2 C5 2.1(6) . . . . ?
C2 C3 N2 C1 1.1(5) . . . . ?
C2 C3 N2 C5 178.4(4) . . . . ?
C1 N2 C5 C6 89.9(5) . . . . ?
C3 N2 C5 C6 -87.0(5) . . . . ?
N2 C5 C6 C7 -175.8(3) . . . . ?
C5 C6 C7 C8 -72.0(5) . . . . ?
C6 C7 C8 N3 -174.2(3) . . . . ?
C7 C8 N3 C9 86.2(5) . . . . ?
C7 C8 N3 C11 -92.3(5) . . . . ?
C11 N3 C9 N4 -0.4(5) . . . . ?
C8 N3 C9 N4 -179.1(4) . . . . ?
C11 N3 C9 C12 -179.1(4) . . . . ?
C8 N3 C9 C12 2.3(7) . . . . ?
N3 C9 N4 C10 0.4(5) . . . . ?
C12 C9 N4 C10 179.0(4) . . . . ?
N3 C9 N4 Cu3 -174.8(3) . . . 1_465 ?
C12 C9 N4 Cu3 3.9(6) . . . 1_465 ?
C9 N4 C10 C11 -0.2(5) . . . . ?
Cu3 N4 C10 C11 175.2(3) 1_465 . . . ?
N4 C10 C11 N3 -0.1(5) . . . . ?
C9 N3 C11 C10 0.3(5) . . . . ?
C8 N3 C11 C10 178.9(4) . . . . ?
C14 N5 C13 N6 0.4(5) . . . . ?
Cu2 N5 C13 N6 -179.7(3) . . . . ?
C14 N5 C13 C16 178.9(4) . . . . ?
Cu2 N5 C13 C16 -1.2(6) . . . . ?
N5 C13 N6 C15 0.1(5) . . . . ?
C16 C13 N6 C15 -178.4(4) . . . . ?
N5 C13 N6 C17 -178.2(4) . . . . ?
C16 C13 N6 C17 3.3(6) . . . . ?
C13 N5 C14 C15 -0.8(5) . . . . ?
Cu2 N5 C14 C15 179.3(3) . . . . ?
N5 C14 C15 N6 0.9(5) . . . . ?
C13 N6 C15 C14 -0.6(5) . . . . ?
C17 N6 C15 C14 177.7(4) . . . . ?
C13 N6 C17 C18 -166.9(4) . . . . ?
C15 N6 C17 C18 15.1(6) . . . . ?
N6 C17 C18 C18 179.7(4) . . . 2_676 ?

_refine_diff_density_max         1.888
_refine_diff_density_min         -0.967
_refine_diff_density_rms         0.198

####################################################################### 
# 
# 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_yf4-9c_a
_database_code_depnum_ccdc_archive 'CCDC 1888944'
loop_
_audit_author_name
_audit_author_address
'Simon J. Teat'
;Advanced Light Source
United States of America
;
_audit_update_record             
;
2019-01-05 deposited with the CCDC.	2019-04-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H21 Cu I N5'
_chemical_formula_weight         509.85

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0034 0.0017
'XDISP Program in WinGX S.Brennan & P.L.Cowan Rev.Sci.Instrum.63,850 1992'
H H 0.0000 0.0000
'XDISP Program in WinGX S.Brennan & P.L.Cowan Rev.Sci.Instrum.63,850 1992'
N N 0.0065 0.0035
'XDISP Program in WinGX S.Brennan & P.L.Cowan Rev.Sci.Instrum.63,850 1992'
Cu Cu 0.3203 1.3289
'XDISP Program in WinGX S.Brennan & P.L.Cowan Rev.Sci.Instrum.63,850 1992'
I I -0.3993 1.9038
'XDISP Program in WinGX S.Brennan & P.L.Cowan Rev.Sci.Instrum.63,850 1992'

_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                   9.4723(9)
_cell_length_b                   10.8047(10)
_cell_length_c                   10.9194(11)
_cell_angle_alpha                69.009(3)
_cell_angle_beta                 64.607(3)
_cell_angle_gamma                80.659(3)
_cell_volume                     942.53(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9786
_cell_measurement_theta_min      3.2176
_cell_measurement_theta_max      33.4062

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.796
_exptl_crystal_F_000             504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    2.984
_shelx_estimated_absorpt_T_min   0.663
_shelx_estimated_absorpt_T_max   0.841
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.655
_exptl_absorpt_correction_T_max  0.841
_exptl_absorpt_process_details   'SADABS 2016/2 Bruker AXS Madison WI USA'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.7288
_diffrn_radiation_type           synchrotron
_diffrn_source                   'Advanced Light Source beamline 12.2.1'
_diffrn_measurement_device_type  'Bruker D8 with PHOTONII detector'
_diffrn_measurement_method       'ω/θ shutterless scans'
_diffrn_detector_area_resol_mean 7.39
_diffrn_reflns_number            33821
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.070
_diffrn_reflns_theta_max         33.406
_diffrn_reflns_theta_full        25.930
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6773
_reflns_number_gt                5987
_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 APEX 3'
_computing_cell_refinement       'Bruker SAINT v8.38a'
_computing_data_reduction        'Bruker SAINT v8.38a'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL & local programs'
_refine_special_details          
;
 All non-hydrogen atoms were refined anisotropically. Hydrogen
 atoms placed geometrically constrained and refined using a riding
 model. Geometrical and displacement parameter restraints were using
 in modelling the disorder.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0233P)²+1.0563P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'Dual space'
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6773
_refine_ls_number_parameters     462
_refine_ls_number_restraints     20
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0301
_refine_ls_wR_factor_ref         0.0722
_refine_ls_wR_factor_gt          0.0674
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.129
_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 1.04738(3) 0.90876(3) 0.09878(3) 0.02584(6) Uani 1 1 d . . . . .
I1 I 1.11380(2) 0.87884(2) -0.14834(2) 0.02783(5) Uani 1 1 d . . . . .
N1 N 0.9387(16) 0.7456(16) 0.2584(13) 0.0250(17) Uani 0.560(5) 1 d . . P A 1
N2 N 0.8461(19) 0.7539(13) 0.3880(15) 0.0285(19) Uani 0.560(5) 1 d . . P A 1
N3 N 0.7993(13) 0.6333(10) 0.4823(9) 0.0328(15) Uani 0.560(5) 1 d . . P A 1
C1 C 0.9506(12) 0.6100(9) 0.2734(9) 0.0251(15) Uani 0.560(5) 1 d . . P A 1
C2 C 1.0343(9) 0.5489(9) 0.1719(9) 0.0323(14) Uani 0.560(5) 1 d . . P A 1
H2A H 1.097682 0.597203 0.075861 0.039 Uiso 0.560(5) 1 calc R U P A 1
C3 C 1.0201(10) 0.4122(8) 0.2191(10) 0.0429(16) Uani 0.560(5) 1 d . . P A 1
H3A H 1.071827 0.365657 0.152249 0.051 Uiso 0.560(5) 1 calc R U P A 1
C4 C 0.9317(10) 0.3406(7) 0.3627(9) 0.0443(16) Uani 0.560(5) 1 d . . P A 1
H4A H 0.924954 0.247149 0.389528 0.053 Uiso 0.560(5) 1 calc R U P A 1
C5 C 0.8552(11) 0.4004(8) 0.4649(9) 0.0409(16) Uani 0.560(5) 1 d . . P A 1
H5A H 0.800323 0.351371 0.562884 0.049 Uiso 0.560(5) 1 calc R U P A 1
C6 C 0.8630(14) 0.5400(12) 0.4152(9) 0.0333(16) Uani 0.560(5) 1 d . . P A 1
C7 C 0.6912(7) 0.6171(6) 0.6317(6) 0.0437(15) Uani 0.560(5) 1 d D . P A 1
H7A H 0.708546 0.689255 0.659445 0.052 Uiso 0.560(5) 1 calc R U P A 1
H7B H 0.714505 0.531944 0.694665 0.052 Uiso 0.560(5) 1 calc R U P A 1
C8 C 0.5189(7) 0.6193(5) 0.6556(5) 0.0456(14) Uani 0.560(5) 1 d D . P A 1
H8A H 0.493308 0.705065 0.594986 0.055 Uiso 0.560(5) 1 calc R U P A 1
H8B H 0.499951 0.547566 0.628179 0.055 Uiso 0.560(5) 1 calc R U P A 1
C9 C 0.4170(7) 0.6005(6) 0.8106(6) 0.0592(18) Uani 0.560(5) 1 d D . P A 1
H9A H 0.308248 0.624804 0.820358 0.071 Uiso 0.560(5) 1 calc R U P A 1
H9B H 0.451219 0.662565 0.840636 0.071 Uiso 0.560(5) 1 calc R U P A 1
C10 C 0.4182(6) 0.4624(6) 0.9110(6) 0.0568(18) Uani 0.560(5) 1 d D . P A 1
H10A H 0.527177 0.428910 0.886834 0.068 Uiso 0.560(5) 1 calc R U P A 1
H10B H 0.375110 0.464296 1.010449 0.068 Uiso 0.560(5) 1 calc R U P A 1
C11 C 0.3314(8) 0.3785(6) 0.9021(7) 0.069(3) Uani 0.560(5) 1 d D . P A 1
H11A H 0.369174 0.383508 0.800689 0.083 Uiso 0.560(5) 1 calc R U P A 1
H11B H 0.221126 0.409191 0.933073 0.083 Uiso 0.560(5) 1 calc R U P A 1
C12 C 0.3382(6) 0.2384(6) 0.9901(8) 0.0482(15) Uani 0.560(5) 1 d D . P A 1
H12A H 0.318530 0.233768 1.088269 0.058 Uiso 0.560(5) 1 calc R U P A 1
H12B H 0.256067 0.187211 0.996577 0.058 Uiso 0.560(5) 1 calc R U P A 1
N4 N 0.4931(7) 0.1802(5) 0.9253(7) 0.0319(11) Uani 0.560(5) 1 d . . P A 1
C13 C 0.6127(11) 0.1687(9) 0.9658(11) 0.0299(14) Uani 0.560(5) 1 d . . P A 1
H13A H 0.608655 0.202845 1.036197 0.036 Uiso 0.560(5) 1 calc R U P A 1
N5 N 0.7352(14) 0.1052(13) 0.8972(7) 0.0250(14) Uani 0.560(5) 1 d . . P A 1
C14 C 0.6982(8) 0.0933(6) 0.7890(9) 0.0236(11) Uani 0.560(5) 1 d . . P A 1
C15 C 0.7865(9) 0.0363(7) 0.6831(8) 0.0325(13) Uani 0.560(5) 1 d . . P A 1
H15A H 0.891297 0.007548 0.667105 0.039 Uiso 0.560(5) 1 calc R U P A 1
C16 C 0.7126(9) 0.0235(6) 0.6006(6) 0.0430(13) Uani 0.560(5) 1 d . . P A 1
H16A H 0.768729 -0.014009 0.526156 0.052 Uiso 0.560(5) 1 calc R U P A 1
C17 C 0.5575(12) 0.0652(7) 0.6269(10) 0.0471(17) Uani 0.560(5) 1 d . . P A 1
H17A H 0.511114 0.054483 0.569564 0.056 Uiso 0.560(5) 1 calc R U P A 1
C18 C 0.4701(8) 0.1206(6) 0.7314(7) 0.0396(12) Uani 0.560(5) 1 d . . P A 1
H18A H 0.364989 0.148917 0.748204 0.048 Uiso 0.560(5) 1 calc R U P A 1
C19 C 0.5451(7) 0.1330(6) 0.8118(7) 0.0271(10) Uani 0.560(5) 1 d . . P A 1
N1' N 0.9162(18) 0.7529(18) 0.2888(13) 0.0181(17) Uani 0.440(5) 1 d . . P A 2
N2' N 0.840(3) 0.7738(17) 0.411(2) 0.030(2) Uani 0.440(5) 1 d . . P A 2
N3' N 0.7939(15) 0.6513(13) 0.5134(11) 0.0301(17) Uani 0.440(5) 1 d . . P A 2
C1' C 0.9224(15) 0.6226(14) 0.3067(12) 0.0255(19) Uani 0.440(5) 1 d . . P A 2
C2' C 0.9858(10) 0.5516(12) 0.2071(12) 0.0317(19) Uani 0.440(5) 1 d . . P A 2
H2'A H 1.041204 0.595661 0.107748 0.038 Uiso 0.440(5) 1 calc R U P A 2
C3' C 0.9639(12) 0.4160(11) 0.2602(13) 0.043(2) Uani 0.440(5) 1 d . . P A 2
H3'A H 1.004874 0.365072 0.197018 0.052 Uiso 0.440(5) 1 calc R U P A 2
C4' C 0.8796(14) 0.3524(10) 0.4105(14) 0.054(3) Uani 0.440(5) 1 d . . P A 2
H4'A H 0.868317 0.258873 0.444282 0.065 Uiso 0.440(5) 1 calc R U P A 2
C5' C 0.8154(15) 0.4176(12) 0.5063(13) 0.049(2) Uani 0.440(5) 1 d . . P A 2
H5'A H 0.755947 0.373455 0.604866 0.059 Uiso 0.440(5) 1 calc R U P A 2
C6' C 0.8413(16) 0.5549(13) 0.4526(12) 0.031(2) Uani 0.440(5) 1 d . . P A 2
C7' C 0.7103(7) 0.6417(10) 0.6624(8) 0.0432(19) Uani 0.440(5) 1 d D . P A 2
H7'A H 0.759833 0.700455 0.684179 0.052 Uiso 0.440(5) 1 calc R U P A 2
H7'B H 0.718364 0.549629 0.722856 0.052 Uiso 0.440(5) 1 calc R U P A 2
C8' C 0.5405(6) 0.6796(5) 0.6996(6) 0.0326(12) Uani 0.220(3) 1 d D . P A 2
H8'A H 0.495533 0.689028 0.796145 0.039 Uiso 0.440(5) 1 calc R U P A 2
H8'B H 0.533782 0.767579 0.630960 0.039 Uiso 0.440(5) 1 calc R U P A 2
C9' C 0.4430(7) 0.5859(6) 0.6988(10) 0.060(3) Uani 0.220(3) 1 d D . P A 2
H9'A H 0.491151 0.568102 0.606306 0.072 Uiso 0.220(3) 1 calc R U P A 2
H9'B H 0.337612 0.624584 0.710823 0.072 Uiso 0.220(3) 1 calc R U P A 2
C10' C 0.4300(11) 0.4507(7) 0.8278(11) 0.027(2) Uani 0.220(3) 1 d D . P A 2
H10C H 0.537267 0.417099 0.815248 0.032 Uiso 0.220(3) 1 calc R U P A 2
H10D H 0.383021 0.472082 0.918204 0.032 Uiso 0.220(3) 1 calc R U P A 2
C11' C 0.3385(7) 0.3408(6) 0.8455(9) 0.0488(19) Uani 0.220(3) 1 d D . P A 2
H11C H 0.368262 0.335732 0.748695 0.059 Uiso 0.220(3) 1 calc R U P A 2
H11D H 0.227125 0.368158 0.879795 0.059 Uiso 0.220(3) 1 calc R U P A 2
C12' C 0.3483(7) 0.2022(7) 0.9413(7) 0.0390(15) Uani 0.220(3) 1 d D . P A 2
H12C H 0.317136 0.203324 1.039803 0.047 Uiso 0.440(5) 1 calc R U P A 2
H12D H 0.273888 0.145312 0.944427 0.047 Uiso 0.440(5) 1 calc R U P A 2
N4' N 0.5062(7) 0.1452(7) 0.8920(8) 0.0297(13) Uani 0.440(5) 1 d . . P A 2
C13' C 0.6143(14) 0.1427(10) 0.9444(13) 0.0261(16) Uani 0.440(5) 1 d . . P A 2
H13B H 0.591793 0.162315 1.029069 0.031 Uiso 0.440(5) 1 calc R U P A 2
N5' N 0.7541(17) 0.1096(18) 0.8627(9) 0.0239(17) Uani 0.440(5) 1 d . . P A 2
C14' C 0.7326(9) 0.0638(9) 0.7671(10) 0.0214(14) Uani 0.440(5) 1 d . . P A 2
C15' C 0.8353(9) 0.0079(9) 0.6660(10) 0.0283(14) Uani 0.440(5) 1 d . . P A 2
H15B H 0.940039 -0.012665 0.656775 0.034 Uiso 0.440(5) 1 calc R U P A 2
C16' C 0.7812(9) -0.0170(9) 0.5788(7) 0.0388(15) Uani 0.440(5) 1 d . . P A 2
H16B H 0.849133 -0.056431 0.508747 0.047 Uiso 0.440(5) 1 calc R U P A 2
C17' C 0.6264(10) 0.0151(11) 0.5918(8) 0.048(2) Uani 0.440(5) 1 d . . P A 2
H17B H 0.593404 -0.002378 0.528877 0.058 Uiso 0.440(5) 1 calc R U P A 2
C18' C 0.5205(9) 0.0711(11) 0.6922(10) 0.0412(19) Uani 0.440(5) 1 d . . P A 2
H18B H 0.415745 0.091312 0.701337 0.049 Uiso 0.440(5) 1 calc R U P A 2
C19' C 0.5782(9) 0.0958(8) 0.7796(8) 0.0300(14) Uani 0.440(5) 1 d . . P A 2
C8" C 0.5405(6) 0.6796(5) 0.6996(6) 0.0326(12) Uani 0.220(3) 1 d . . P A 3
C9" C 0.4430(7) 0.5859(6) 0.6988(10) 0.060(3) Uani 0.220(3) 1 d D . P A 3
H9"A H 0.337086 0.605540 0.763337 0.072 Uiso 0.220(3) 1 calc R U P A 3
H9"B H 0.444029 0.625515 0.601425 0.072 Uiso 0.220(3) 1 calc R U P A 3
C10" C 0.4339(12) 0.4492(8) 0.7242(11) 0.036(2) Uani 0.220(3) 1 d D . P A 3
H10E H 0.542522 0.416637 0.706594 0.043 Uiso 0.220(3) 1 calc R U P A 3
H10F H 0.415257 0.446598 0.642630 0.043 Uiso 0.220(3) 1 calc R U P A 3
C11" C 0.3385(7) 0.3408(6) 0.8455(9) 0.0488(19) Uani 0.220(3) 1 d D . P A 3
H11E H 0.262467 0.329549 0.810318 0.059 Uiso 0.220(3) 1 calc R U P A 3
H11F H 0.278581 0.386700 0.916747 0.059 Uiso 0.220(3) 1 calc R U P A 3
C12" C 0.3483(7) 0.2022(7) 0.9413(7) 0.0390(15) Uani 0.220(3) 1 d . . P A 3


_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 2.014(16) . ?
Cu1 N5 2.058(13) 2_766 ?
Cu1 N5' 2.062(16) 2_766 ?
Cu1 N1' 2.156(16) . ?
Cu1 I1 2.6239(4) . ?
Cu1 I1 2.6333(4) 2_775 ?
Cu1 Cu1 2.7177(5) 2_775 ?
N1 N2 1.334(15) . ?
N1 C1 1.406(17) . ?
N2 N3 1.338(17) . ?
N3 C6 1.367(11) . ?
N3 C7 1.470(10) . ?
C1 C2 1.375(10) . ?
C1 C6 1.386(12) . ?
C2 C3 1.387(13) . ?
C2 H2A 0.9500 . ?
C3 C4 1.405(11) . ?
C3 H3A 0.9500 . ?
C4 C5 1.363(9) . ?
C4 H4A 0.9500 . ?
C5 C6 1.411(15) . ?
C5 H5A 0.9500 . ?
C7 C8 1.536(7) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.502(6) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.504(6) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.371(8) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.483(7) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 N4 1.475(8) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
N4 C13 1.356(10) . ?
N4 C19 1.373(7) . ?
C13 N5 1.321(14) . ?
C13 H13A 0.9500 . ?
N5 C14 1.420(13) . ?
C14 C19 1.384(8) . ?
C14 C15 1.389(8) . ?
C15 C16 1.408(10) . ?
C15 H15A 0.9500 . ?
C16 C17 1.400(11) . ?
C16 H16A 0.9500 . ?
C17 C18 1.366(10) . ?
C17 H17A 0.9500 . ?
C18 C19 1.394(7) . ?
C18 H18A 0.9500 . ?
N1' N2' 1.299(17) . ?
N1' C1' 1.34(2) . ?
N2' N3' 1.38(2) . ?
N3' C6' 1.347(12) . ?
N3' C7' 1.445(11) . ?
C1' C6' 1.400(15) . ?
C1' C2' 1.421(14) . ?
C2' C3' 1.383(17) . ?
C2' H2'A 0.9500 . ?
C3' C4' 1.431(16) . ?
C3' H3'A 0.9500 . ?
C4' C5' 1.344(13) . ?
C4' H4'A 0.9500 . ?
C5' C6' 1.405(18) . ?
C5' H5'A 0.9500 . ?
C7' C8' 1.504(7) . ?
C7' H7'A 0.9900 . ?
C7' H7'B 0.9900 . ?
C8' C9' 1.483(7) . ?
C8' H8'A 0.9900 . ?
C8' H8'B 0.9900 . ?
C9' C10' 1.603(8) . ?
C9' H9'A 0.9900 . ?
C9' H9'B 0.9900 . ?
C10' C11' 1.491(8) . ?
C10' H10C 0.9900 . ?
C10' H10D 0.9900 . ?
C11' C12' 1.504(7) . ?
C11' H11C 0.9900 . ?
C11' H11D 0.9900 . ?
C12' N4' 1.468(9) . ?
C12' H12C 0.9900 . ?
C12' H12D 0.9900 . ?
N4' C13' 1.363(12) . ?
N4' C19' 1.375(9) . ?
C13' N5' 1.318(17) . ?
C13' H13B 0.9500 . ?
N5' C14' 1.400(16) . ?
C14' C15' 1.377(10) . ?
C14' C19' 1.406(10) . ?
C15' C16' 1.375(11) . ?
C15' H15B 0.9500 . ?
C16' C17' 1.407(10) . ?
C16' H16B 0.9500 . ?
C17' C18' 1.382(12) . ?
C17' H17B 0.9500 . ?
C18' C19' 1.399(12) . ?
C18' H18B 0.9500 . ?
C8" C9" 1.483(7) . ?
C9" C10" 1.412(8) . ?
C9" H9"A 0.9900 . ?
C9" H9"B 0.9900 . ?
C10" C11" 1.465(8) . ?
C10" H10E 0.9900 . ?
C10" H10F 0.9900 . ?
C11" C12" 1.504(7) . ?
C11" H11E 0.9900 . ?
C11" H11F 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Cu1 N5 103.2(5) . 2_766 ?
N1 Cu1 N5' 97.3(6) . 2_766 ?
N5 Cu1 N5' 9.2(4) 2_766 2_766 ?
N5' Cu1 N1' 97.2(6) 2_766 . ?
N1 Cu1 I1 109.3(3) . . ?
N5 Cu1 I1 102.0(2) 2_766 . ?
N5' Cu1 I1 110.9(3) 2_766 . ?
N1' Cu1 I1 116.9(4) . . ?
N1 Cu1 I1 109.5(3) . 2_775 ?
N5 Cu1 I1 114.0(4) 2_766 2_775 ?
I1 Cu1 I1 117.745(11) . 2_775 ?
N1 Cu1 Cu1 129.9(4) . 2_775 ?
N5 Cu1 Cu1 126.6(3) 2_766 2_775 ?
I1 Cu1 Cu1 59.042(12) . 2_775 ?
I1 Cu1 Cu1 58.703(12) 2_775 2_775 ?
Cu1 I1 Cu1 62.256(11) . 2_775 ?
N2 N1 C1 106.1(12) . . ?
N2 N1 Cu1 119.6(11) . . ?
C1 N1 Cu1 133.8(7) . . ?
N1 N2 N3 110.5(10) . . ?
N2 N3 C6 109.5(9) . . ?
N2 N3 C7 120.6(8) . . ?
C6 N3 C7 129.8(9) . . ?
C2 C1 C6 122.6(8) . . ?
C2 C1 N1 129.1(9) . . ?
C6 C1 N1 108.3(7) . . ?
C1 C2 C3 115.6(7) . . ?
C1 C2 H2A 122.2 . . ?
C3 C2 H2A 122.2 . . ?
C2 C3 C4 122.0(7) . . ?
C2 C3 H3A 119.0 . . ?
C4 C3 H3A 119.0 . . ?
C5 C4 C3 122.4(7) . . ?
C5 C4 H4A 118.8 . . ?
C3 C4 H4A 118.8 . . ?
C4 C5 C6 115.5(7) . . ?
C4 C5 H5A 122.3 . . ?
C6 C5 H5A 122.3 . . ?
N3 C6 C1 105.6(10) . . ?
N3 C6 C5 132.6(9) . . ?
C1 C6 C5 121.7(7) . . ?
N3 C7 C8 112.9(6) . . ?
N3 C7 H7A 109.0 . . ?
C8 C7 H7A 109.0 . . ?
N3 C7 H7B 109.0 . . ?
C8 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C9 C8 C7 109.4(5) . . ?
C9 C8 H8A 109.8 . . ?
C7 C8 H8A 109.8 . . ?
C9 C8 H8B 109.8 . . ?
C7 C8 H8B 109.8 . . ?
H8A C8 H8B 108.3 . . ?
C8 C9 C10 114.9(4) . . ?
C8 C9 H9A 108.5 . . ?
C10 C9 H9A 108.5 . . ?
C8 C9 H9B 108.5 . . ?
C10 C9 H9B 108.5 . . ?
H9A C9 H9B 107.5 . . ?
C11 C10 C9 111.2(5) . . ?
C11 C10 H10A 109.4 . . ?
C9 C10 H10A 109.4 . . ?
C11 C10 H10B 109.4 . . ?
C9 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
C10 C11 C12 113.7(5) . . ?
C10 C11 H11A 108.8 . . ?
C12 C11 H11A 108.8 . . ?
C10 C11 H11B 108.8 . . ?
C12 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
N4 C12 C11 110.1(5) . . ?
N4 C12 H12A 109.6 . . ?
C11 C12 H12A 109.6 . . ?
N4 C12 H12B 109.6 . . ?
C11 C12 H12B 109.6 . . ?
H12A C12 H12B 108.2 . . ?
C13 N4 C19 107.6(6) . . ?
C13 N4 C12 125.0(6) . . ?
C19 N4 C12 127.3(5) . . ?
N5 C13 N4 113.1(7) . . ?
N5 C13 H13A 123.5 . . ?
N4 C13 H13A 123.5 . . ?
C13 N5 C14 103.2(10) . . ?
C13 N5 Cu1 125.9(8) . 2_766 ?
C14 N5 Cu1 127.5(7) . 2_766 ?
C19 C14 C15 120.9(8) . . ?
C19 C14 N5 109.9(7) . . ?
C15 C14 N5 128.8(8) . . ?
C14 C15 C16 116.5(7) . . ?
C14 C15 H15A 121.7 . . ?
C16 C15 H15A 121.7 . . ?
C17 C16 C15 120.8(6) . . ?
C17 C16 H16A 119.6 . . ?
C15 C16 H16A 119.6 . . ?
C18 C17 C16 122.8(6) . . ?
C18 C17 H17A 118.6 . . ?
C16 C17 H17A 118.6 . . ?
C17 C18 C19 115.6(6) . . ?
C17 C18 H18A 122.2 . . ?
C19 C18 H18A 122.2 . . ?
N4 C19 C14 105.3(5) . . ?
N4 C19 C18 131.4(6) . . ?
C14 C19 C18 123.3(7) . . ?
N2' N1' C1' 110.6(15) . . ?
N2' N1' Cu1 121.0(14) . . ?
C1' N1' Cu1 127.3(7) . . ?
N1' N2' N3' 106.5(12) . . ?
C6' N3' N2' 110.6(10) . . ?
C6' N3' C7' 129.8(12) . . ?
N2' N3' C7' 119.6(10) . . ?
N1' C1' C6' 108.2(9) . . ?
N1' C1' C2' 131.9(12) . . ?
C6' C1' C2' 119.9(12) . . ?
C3' C2' C1' 117.6(11) . . ?
C3' C2' H2'A 121.2 . . ?
C1' C2' H2'A 121.2 . . ?
C2' C3' C4' 120.0(10) . . ?
C2' C3' H3'A 120.0 . . ?
C4' C3' H3'A 120.0 . . ?
C5' C4' C3' 123.6(10) . . ?
C5' C4' H4'A 118.2 . . ?
C3' C4' H4'A 118.2 . . ?
C4' C5' C6' 116.2(10) . . ?
C4' C5' H5'A 121.9 . . ?
C6' C5' H5'A 121.9 . . ?
N3' C6' C1' 104.0(11) . . ?
N3' C6' C5' 133.2(12) . . ?
C1' C6' C5' 122.7(10) . . ?
N3' C7' C8' 112.5(7) . . ?
N3' C7' H7'A 109.1 . . ?
C8' C7' H7'A 109.1 . . ?
N3' C7' H7'B 109.1 . . ?
C8' C7' H7'B 109.1 . . ?
H7'A C7' H7'B 107.8 . . ?
C9' C8' C7' 115.7(6) . . ?
C9' C8' H8'A 108.4 . . ?
C7' C8' H8'A 108.4 . . ?
C9' C8' H8'B 108.4 . . ?
C7' C8' H8'B 108.4 . . ?
H8'A C8' H8'B 107.4 . . ?
C8' C9' C10' 108.6(6) . . ?
C8' C9' H9'A 110.0 . . ?
C10' C9' H9'A 110.0 . . ?
C8' C9' H9'B 110.0 . . ?
C10' C9' H9'B 110.0 . . ?
H9'A C9' H9'B 108.4 . . ?
C11' C10' C9' 117.7(6) . . ?
C11' C10' H10C 107.9 . . ?
C9' C10' H10C 107.9 . . ?
C11' C10' H10D 107.9 . . ?
C9' C10' H10D 107.9 . . ?
H10C C10' H10D 107.2 . . ?
C10' C11' C12' 121.2(7) . . ?
C10' C11' H11C 107.0 . . ?
C12' C11' H11C 107.0 . . ?
C10' C11' H11D 107.0 . . ?
C12' C11' H11D 107.0 . . ?
H11C C11' H11D 106.8 . . ?
N4' C12' C11' 112.1(5) . . ?
N4' C12' H12C 109.2 . . ?
C11' C12' H12C 109.2 . . ?
N4' C12' H12D 109.2 . . ?
C11' C12' H12D 109.2 . . ?
H12C C12' H12D 107.9 . . ?
C13' N4' C19' 107.1(7) . . ?
C13' N4' C12' 124.8(8) . . ?
C19' N4' C12' 127.9(7) . . ?
N5' C13' N4' 111.5(10) . . ?
N5' C13' H13B 124.3 . . ?
N4' C13' H13B 124.3 . . ?
C13' N5' C14' 106.4(12) . . ?
C15' C14' N5' 131.5(9) . . ?
C15' C14' C19' 121.1(8) . . ?
N5' C14' C19' 107.1(8) . . ?
C16' C15' C14' 117.8(7) . . ?
C16' C15' H15B 121.1 . . ?
C14' C15' H15B 121.1 . . ?
C15' C16' C17' 120.9(8) . . ?
C15' C16' H16B 119.6 . . ?
C17' C16' H16B 119.6 . . ?
C18' C17' C16' 122.8(7) . . ?
C18' C17' H17B 118.6 . . ?
C16' C17' H17B 118.6 . . ?
C17' C18' C19' 115.3(6) . . ?
C17' C18' H18B 122.3 . . ?
C19' C18' H18B 122.3 . . ?
N4' C19' C18' 131.2(7) . . ?
N4' C19' C14' 106.6(7) . . ?
C18' C19' C14' 122.1(8) . . ?
C10" C9" C8" 140.0(7) . . ?
C10" C9" H9"A 102.0 . . ?
C8" C9" H9"A 102.0 . . ?
C10" C9" H9"B 102.0 . . ?
C8" C9" H9"B 102.0 . . ?
H9"A C9" H9"B 104.8 . . ?
C9" C10" C11" 133.9(9) . . ?
C9" C10" H10E 103.7 . . ?
C11" C10" H10E 103.7 . . ?
C9" C10" H10F 103.7 . . ?
C11" C10" H10F 103.7 . . ?
H10E C10" H10F 105.4 . . ?
C10" C11" C12" 142.8(6) . . ?
C10" C11" H11E 101.3 . . ?
C12" C11" H11E 101.3 . . ?
C10" C11" H11F 101.3 . . ?
C12" C11" H11F 101.3 . . ?
H11E C11" H11F 104.5 . . ?

_refine_diff_density_max         0.864
_refine_diff_density_min         -1.526
_refine_diff_density_rms         0.101

####################################################################### 
# 
# 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_yf3-124c_a
_database_code_depnum_ccdc_archive 'CCDC 1888942'
loop_
_audit_author_name
_audit_author_address
'Simon J. Teat'
;Advanced Light Source
United States of America
;
_audit_update_record             
;
2019-01-05 deposited with the CCDC.	2019-04-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H18 Cu2 I2 N6'
_chemical_formula_weight         687.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0040 0.0020
'XDISP Program in WinGX S.Brennan & P.L.Cowan Rev.Sci.Instrum.63,850 1992'
H H 0.0000 0.0000
'XDISP Program in WinGX S.Brennan & P.L.Cowan Rev.Sci.Instrum.63,850 1992'
N N 0.0076 0.0040
'XDISP Program in WinGX S.Brennan & P.L.Cowan Rev.Sci.Instrum.63,850 1992'
Cu Cu 0.2913 1.4803
'XDISP Program in WinGX S.Brennan & P.L.Cowan Rev.Sci.Instrum.63,850 1992'
I I -0.3071 2.1212
'XDISP Program in WinGX S.Brennan & P.L.Cowan Rev.Sci.Instrum.63,850 1992'

_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                   8.3419(5)
_cell_length_b                   10.1955(6)
_cell_length_c                   13.6890(8)
_cell_angle_alpha                76.369(2)
_cell_angle_beta                 74.522(2)
_cell_angle_gamma                66.570(2)
_cell_volume                     1018.40(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9963
_cell_measurement_theta_min      2.731
_cell_measurement_theta_max      34.884

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.241
_exptl_crystal_F_000             652
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.020
_exptl_crystal_size_mid          0.010
_exptl_crystal_size_min          0.002
_exptl_absorpt_coefficient_mu    6.440
_shelx_estimated_absorpt_T_min   0.882
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.777
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_process_details   'SADABS 2014/5 Bruker AXS Madison WI USA'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.7749
_diffrn_radiation_type           synchrotron
_diffrn_source                   'Advanced Light Source station 11.3.1'
_diffrn_measurement_device_type  'Bruker D8 with PHOTONII detector'
_diffrn_measurement_method       'ω/θ shutterless scans'
_diffrn_detector_area_resol_mean 7.39
_diffrn_reflns_number            17410
_diffrn_reflns_av_unetI/netI     0.0585
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.400
_diffrn_reflns_theta_max         34.915
_diffrn_reflns_theta_full        27.706
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6790
_reflns_number_gt                5275
_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 APEX 3'
_computing_cell_refinement       'Bruker SAINT v8.38a'
_computing_data_reduction        'Bruker SAINT v8.38a'
_computing_structure_solution    'Bruker SHELXTL 2014/5'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL & local programs'
_refine_special_details          
;
 All non-hydrogen atoms were refined anisotropically.
 Hydrogen atoms were placed geometrically and refined using a riding model.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0291P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6790
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0336
_refine_ls_wR_factor_ref         0.0809
_refine_ls_wR_factor_gt          0.0755
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_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 0.59516(6) 0.08280(4) 0.46848(3) 0.02457(10) Uani 1 1 d . . . . .
Cu2 Cu 0.28637(6) 0.08929(4) 0.68511(3) 0.02303(10) Uani 1 1 d . . . . .
I1 I 0.89042(3) 0.05236(2) 0.34566(2) 0.02211(6) Uani 1 1 d . . . . .
I2 I 0.63571(3) -0.07970(2) 0.65006(2) 0.02188(6) Uani 1 1 d . . . . .
N1 N 0.4187(4) 0.2734(3) 0.5099(2) 0.0189(5) Uani 1 1 d . . . . .
N2 N 0.2901(4) 0.2768(3) 0.5908(2) 0.0202(6) Uani 1 1 d . . . . .
N3 N 0.1756(4) 0.4150(3) 0.5926(2) 0.0197(5) Uani 1 1 d . . . . .
C1 C 0.3879(4) 0.4106(3) 0.4584(2) 0.0180(6) Uani 1 1 d . . . . .
C2 C 0.4875(4) 0.4615(4) 0.3691(3) 0.0212(7) Uani 1 1 d . . . . .
H2A H 0.5915 0.3980 0.3320 0.025 Uiso 1 1 calc R U . . .
C3 C 0.4269(5) 0.6085(4) 0.3377(3) 0.0242(7) Uani 1 1 d . . . . .
H3A H 0.4920 0.6480 0.2783 0.029 Uiso 1 1 calc R U . . .
C4 C 0.2691(5) 0.7023(4) 0.3923(3) 0.0246(7) Uani 1 1 d . . . . .
H4A H 0.2327 0.8032 0.3683 0.030 Uiso 1 1 calc R U . . .
C5 C 0.1677(4) 0.6538(3) 0.4777(3) 0.0220(7) Uani 1 1 d . . . . .
H5A H 0.0604 0.7172 0.5124 0.026 Uiso 1 1 calc R U . . .
C6 C 0.2324(4) 0.5032(3) 0.5113(2) 0.0199(6) Uani 1 1 d . . . . .
C7 C 0.0244(4) 0.4526(4) 0.6782(3) 0.0230(7) Uani 1 1 d . . . . .
H7A H 0.0114 0.3628 0.7204 0.028 Uiso 1 1 calc R U . . .
H7B H -0.0861 0.5086 0.6508 0.028 Uiso 1 1 calc R U . . .
C8 C 0.0479(4) 0.5404(4) 0.7448(3) 0.0217(7) Uani 1 1 d . . . . .
H8A H 0.1574 0.4841 0.7730 0.026 Uiso 1 1 calc R U . . .
H8B H 0.0616 0.6300 0.7027 0.026 Uiso 1 1 calc R U . . .
C9 C -0.1106(4) 0.5788(4) 0.8319(3) 0.0233(7) Uani 1 1 d . . . . .
H9A H -0.1176 0.4892 0.8772 0.028 Uiso 1 1 calc R U . . .
H9B H -0.2210 0.6268 0.8037 0.028 Uiso 1 1 calc R U . . .
C10 C -0.0984(5) 0.6786(4) 0.8947(3) 0.0257(7) Uani 1 1 d . . . . .
H10A H -0.0012 0.6247 0.9336 0.031 Uiso 1 1 calc R U . . .
H10B H -0.0696 0.7600 0.8481 0.031 Uiso 1 1 calc R U . . .
C11 C -0.2731(5) 0.7375(4) 0.9690(3) 0.0284(8) Uani 1 1 d . . . . .
H11A H -0.3707 0.7892 0.9302 0.034 Uiso 1 1 calc R U . . .
H11B H -0.3003 0.6562 1.0166 0.034 Uiso 1 1 calc R U . . .
N4 N -0.2642(4) 0.8364(3) 1.0281(2) 0.0261(6) Uani 1 1 d . . . . .
N5 N -0.2565(4) 0.7944(3) 1.1283(2) 0.0272(7) Uani 1 1 d . . . . .
N6 N -0.2482(4) 0.9005(3) 1.1632(2) 0.0250(6) Uani 1 1 d . . . . .
C12 C -0.2592(4) 0.9709(4) 0.9962(3) 0.0249(7) Uani 1 1 d . . . . .
C13 C -0.2630(5) 1.0628(4) 0.9017(3) 0.0303(8) Uani 1 1 d . . . . .
H13A H -0.2697 1.0347 0.8419 0.036 Uiso 1 1 calc R U . . .
C14 C -0.2565(6) 1.1948(5) 0.9009(3) 0.0354(9) Uani 1 1 d . . . . .
H14A H -0.2563 1.2594 0.8383 0.042 Uiso 1 1 calc R U . . .
C15 C -0.2500(6) 1.2382(5) 0.9892(3) 0.0380(10) Uani 1 1 d . . . . .
H15A H -0.2484 1.3321 0.9847 0.046 Uiso 1 1 calc R U . . .
C16 C -0.2458(5) 1.1495(4) 1.0823(3) 0.0307(8) Uani 1 1 d . . . . .
H16A H -0.2406 1.1794 1.1417 0.037 Uiso 1 1 calc R U . . .
C17 C -0.2498(5) 1.0137(4) 1.0844(3) 0.0234(7) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N1 2.016(3) . ?
Cu1 I1 2.5332(5) . ?
Cu1 Cu1 2.6133(9) 2_656 ?
Cu1 I2 2.6645(5) . ?
Cu1 Cu2 2.7796(6) 2_656 ?
Cu1 I2 2.8431(5) 2_656 ?
Cu2 N6 2.037(3) 2_567 ?
Cu2 N2 2.046(3) . ?
Cu2 I1 2.5980(5) 2_656 ?
Cu2 I2 2.7095(5) . ?
Cu2 Cu1 2.7796(6) 2_656 ?
I1 Cu2 2.5981(5) 2_656 ?
I2 Cu1 2.8431(5) 2_656 ?
N1 N2 1.316(4) . ?
N1 C1 1.366(4) . ?
N2 N3 1.354(4) . ?
N3 C6 1.362(4) . ?
N3 C7 1.466(4) . ?
C1 C6 1.395(4) . ?
C1 C2 1.399(5) . ?
C2 C3 1.377(5) . ?
C2 H2A 0.9500 . ?
C3 C4 1.420(5) . ?
C3 H3A 0.9500 . ?
C4 C5 1.364(5) . ?
C4 H4A 0.9500 . ?
C5 C6 1.415(4) . ?
C5 H5A 0.9500 . ?
C7 C8 1.514(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.513(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.525(5) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.524(5) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 N4 1.467(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
N4 N5 1.349(4) . ?
N4 C12 1.351(5) . ?
N5 N6 1.312(4) . ?
N6 C17 1.380(5) . ?
N6 Cu2 2.037(3) 2_567 ?
C12 C17 1.407(5) . ?
C12 C13 1.407(5) . ?
C13 C14 1.365(6) . ?
C13 H13A 0.9500 . ?
C14 C15 1.402(6) . ?
C14 H14A 0.9500 . ?
C15 C16 1.378(6) . ?
C15 H15A 0.9500 . ?
C16 C17 1.392(5) . ?
C16 H16A 0.9500 . ?

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 I1 124.28(8) . . ?
N1 Cu1 Cu1 102.08(8) . 2_656 ?
I1 Cu1 Cu1 131.76(2) . 2_656 ?
N1 Cu1 I2 101.65(8) . . ?
I1 Cu1 I2 112.097(18) . . ?
Cu1 Cu1 I2 65.181(19) 2_656 . ?
N1 Cu1 Cu2 143.22(8) . 2_656 ?
I1 Cu1 Cu2 58.332(13) . 2_656 ?
Cu1 Cu1 Cu2 77.11(2) 2_656 2_656 ?
I2 Cu1 Cu2 110.660(18) . 2_656 ?
N1 Cu1 I2 90.18(8) . 2_656 ?
I1 Cu1 I2 105.050(17) . 2_656 ?
Cu1 Cu1 I2 58.281(18) 2_656 2_656 ?
I2 Cu1 I2 123.461(17) . 2_656 ?
Cu2 Cu1 I2 57.603(14) 2_656 2_656 ?
N6 Cu2 N2 114.11(11) 2_567 . ?
N6 Cu2 I1 111.43(9) 2_567 2_656 ?
N2 Cu2 I1 119.87(8) . 2_656 ?
N6 Cu2 I2 100.06(9) 2_567 . ?
N2 Cu2 I2 101.34(8) . . ?
I1 Cu2 I2 107.143(16) 2_656 . ?
N6 Cu2 Cu1 147.70(8) 2_567 2_656 ?
N2 Cu2 Cu1 96.56(8) . 2_656 ?
I1 Cu2 Cu1 56.085(13) 2_656 2_656 ?
I2 Cu2 Cu1 62.375(14) . 2_656 ?
Cu1 I1 Cu2 65.584(15) . 2_656 ?
Cu1 I2 Cu2 77.489(14) . . ?
Cu1 I2 Cu1 56.539(17) . 2_656 ?
Cu2 I2 Cu1 60.020(13) . 2_656 ?
N2 N1 C1 108.6(2) . . ?
N2 N1 Cu1 120.3(2) . . ?
C1 N1 Cu1 130.3(2) . . ?
N1 N2 N3 108.5(3) . . ?
N1 N2 Cu2 120.0(2) . . ?
N3 N2 Cu2 131.5(2) . . ?
N2 N3 C6 110.1(2) . . ?
N2 N3 C7 120.4(3) . . ?
C6 N3 C7 129.3(3) . . ?
N1 C1 C6 108.4(3) . . ?
N1 C1 C2 129.8(3) . . ?
C6 C1 C2 121.8(3) . . ?
C3 C2 C1 116.5(3) . . ?
C3 C2 H2A 121.7 . . ?
C1 C2 H2A 121.7 . . ?
C2 C3 C4 121.4(3) . . ?
C2 C3 H3A 119.3 . . ?
C4 C3 H3A 119.3 . . ?
C5 C4 C3 122.8(3) . . ?
C5 C4 H4A 118.6 . . ?
C3 C4 H4A 118.6 . . ?
C4 C5 C6 115.8(3) . . ?
C4 C5 H5A 122.1 . . ?
C6 C5 H5A 122.1 . . ?
N3 C6 C1 104.5(3) . . ?
N3 C6 C5 133.9(3) . . ?
C1 C6 C5 121.7(3) . . ?
N3 C7 C8 111.9(3) . . ?
N3 C7 H7A 109.2 . . ?
C8 C7 H7A 109.2 . . ?
N3 C7 H7B 109.2 . . ?
C8 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
C9 C8 C7 110.9(3) . . ?
C9 C8 H8A 109.5 . . ?
C7 C8 H8A 109.5 . . ?
C9 C8 H8B 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 108.1 . . ?
C8 C9 C10 112.0(3) . . ?
C8 C9 H9A 109.2 . . ?
C10 C9 H9A 109.2 . . ?
C8 C9 H9B 109.2 . . ?
C10 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
C11 C10 C9 110.9(3) . . ?
C11 C10 H10A 109.5 . . ?
C9 C10 H10A 109.5 . . ?
C11 C10 H10B 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 108.0 . . ?
N4 C11 C10 111.4(3) . . ?
N4 C11 H11A 109.4 . . ?
C10 C11 H11A 109.4 . . ?
N4 C11 H11B 109.4 . . ?
C10 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
N5 N4 C12 111.2(3) . . ?
N5 N4 C11 119.7(3) . . ?
C12 N4 C11 129.0(3) . . ?
N6 N5 N4 108.0(3) . . ?
N5 N6 C17 109.1(3) . . ?
N5 N6 Cu2 123.8(2) . 2_567 ?
C17 N6 Cu2 125.7(2) . 2_567 ?
N4 C12 C17 104.4(3) . . ?
N4 C12 C13 134.0(3) . . ?
C17 C12 C13 121.6(3) . . ?
C14 C13 C12 116.1(3) . . ?
C14 C13 H13A 122.0 . . ?
C12 C13 H13A 122.0 . . ?
C13 C14 C15 122.3(4) . . ?
C13 C14 H14A 118.8 . . ?
C15 C14 H14A 118.8 . . ?
C16 C15 C14 122.4(4) . . ?
C16 C15 H15A 118.8 . . ?
C14 C15 H15A 118.8 . . ?
C15 C16 C17 116.2(4) . . ?
C15 C16 H16A 121.9 . . ?
C17 C16 H16A 121.9 . . ?
N6 C17 C16 131.3(3) . . ?
N6 C17 C12 107.2(3) . . ?
C16 C17 C12 121.5(3) . . ?

_refine_diff_density_max         1.578
_refine_diff_density_min         -1.608
_refine_diff_density_rms         0.162

####################################################################### 
# 
# 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_yf3-122d_a
_database_code_depnum_ccdc_archive 'CCDC 1888941'
loop_
_audit_author_name
_audit_author_address
'Simon J. Teat'
;Advanced Light Source
United States of America
;
_audit_update_record             
;
2019-01-05 deposited with the CCDC.	2019-04-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H18 Cu I N6'
_chemical_formula_weight         496.81

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0034 0.0017
'XDISP Program in WinGX S.Brennan & P.L.Cowan Rev.Sci.Instrum.63,850 1992'
H H 0.0000 0.0000
'XDISP Program in WinGX S.Brennan & P.L.Cowan Rev.Sci.Instrum.63,850 1992'
N N 0.0066 0.0035
'XDISP Program in WinGX S.Brennan & P.L.Cowan Rev.Sci.Instrum.63,850 1992'
Cu Cu 0.3201 1.3305
'XDISP Program in WinGX S.Brennan & P.L.Cowan Rev.Sci.Instrum.63,850 1992'
I I -0.3983 1.9061
'XDISP Program in WinGX S.Brennan & P.L.Cowan Rev.Sci.Instrum.63,850 1992'

_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                   9.3371(5)
_cell_length_b                   10.3738(6)
_cell_length_c                   10.4214(6)
_cell_angle_alpha                82.819(2)
_cell_angle_beta                 81.825(2)
_cell_angle_gamma                63.474(2)
_cell_volume                     891.83(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9731
_cell_measurement_theta_min      2.9300
_cell_measurement_theta_max      37.3922

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.850
_exptl_crystal_F_000             488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    3.158
_shelx_estimated_absorpt_T_min   0.632
_shelx_estimated_absorpt_T_max   0.833
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.692
_exptl_absorpt_correction_T_max  0.833
_exptl_absorpt_process_details   'SADABS 2016/2 Bruker AXS Madison WI USA'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.7293
_diffrn_radiation_type           synchrotron
_diffrn_source                   'Advanced Light Source station 11.3.1'
_diffrn_measurement_device_type  'Bruker D8 with PHOTONII detector'
_diffrn_measurement_method       'ω/θ shutterless scans'
_diffrn_detector_area_resol_mean 7.39
_diffrn_reflns_number            37648
_diffrn_reflns_av_unetI/netI     0.0435
_diffrn_reflns_av_R_equivalents  0.0499
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.257
_diffrn_reflns_theta_max         37.422
_diffrn_reflns_theta_full        25.950
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             8586
_reflns_number_gt                7954
_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 APEX 3'
_computing_cell_refinement       'Bruker SAINT v8.38a'
_computing_data_reduction        'Bruker SAINT v8.38a'
_computing_structure_solution    'Bruker SHELXTL 2014/5'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL & local programs'
_refine_special_details          
;
 All non-hydrogen atoms were refined anisotropically. Hydrogen atoms were placed
 geometrically except for the methyl groups which were found in the difference map
 then constrained refined using a riding model.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0246P)²+0.9890P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'Dual space'
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0275(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         8586
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_gt           0.0323
_refine_ls_wR_factor_ref         0.0772
_refine_ls_wR_factor_gt          0.0741
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_restrained_S_all      1.126
_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 0.90849(3) 0.11309(2) 0.09030(2) 0.01382(5) Uani 1 1 d . . . . .
I1 I 0.77152(2) 0.01075(2) -0.04737(2) 0.01243(4) Uani 1 1 d . . . . .
N1 N 0.83234(17) 0.33094(15) 0.05639(14) 0.0127(2) Uani 1 1 d . . . . .
N2 N 0.88281(18) 0.39661(15) 0.12647(14) 0.0129(2) Uani 1 1 d . . . . .
N3 N 0.82371(17) 0.53697(15) 0.08434(14) 0.0120(2) Uani 1 1 d . . . . .
C1 C 0.73628(19) 0.43112(17) -0.03229(16) 0.0115(2) Uani 1 1 d . . . . .
C2 C 0.6493(2) 0.41869(18) -0.12577(16) 0.0134(3) Uani 1 1 d . . . . .
H2A H 0.6512 0.3289 -0.1389 0.016 Uiso 1 1 calc R U . . .
C3 C 0.5607(2) 0.54441(19) -0.19750(17) 0.0152(3) Uani 1 1 d . . . . .
H3A H 0.5002 0.5406 -0.2617 0.018 Uiso 1 1 calc R U . . .
C4 C 0.5570(2) 0.67868(19) -0.17845(17) 0.0159(3) Uani 1 1 d . . . . .
H4A H 0.4936 0.7621 -0.2299 0.019 Uiso 1 1 calc R U . . .
C5 C 0.6423(2) 0.69214(18) -0.08783(17) 0.0143(3) Uani 1 1 d . . . . .
H5A H 0.6412 0.7818 -0.0757 0.017 Uiso 1 1 calc R U . . .
C6 C 0.73100(19) 0.56460(18) -0.01462(16) 0.0120(2) Uani 1 1 d . . . . .
C7 C 0.8523(2) 0.64126(18) 0.14584(16) 0.0130(3) Uani 1 1 d . . . . .
H7A H 0.8793 0.7045 0.0776 0.016 Uiso 1 1 calc R U . . .
H7B H 0.9457 0.5889 0.1974 0.016 Uiso 1 1 calc R U . . .
C8 C 0.7067(2) 0.73421(18) 0.23439(16) 0.0137(3) Uani 1 1 d . . . . .
H8A H 0.7199 0.8190 0.2541 0.016 Uiso 1 1 calc R U . . .
H8B H 0.6091 0.7702 0.1880 0.016 Uiso 1 1 calc R U . . .
C9 C 0.6832(2) 0.6526(2) 0.36146(17) 0.0159(3) Uani 1 1 d . . . . .
H9A H 0.7856 0.6065 0.4023 0.019 Uiso 1 1 calc R U . . .
H9B H 0.6572 0.5749 0.3421 0.019 Uiso 1 1 calc R U . . .
C10 C 0.5500(2) 0.7485(2) 0.45830(18) 0.0184(3) Uani 1 1 d . . . . .
H10A H 0.5617 0.6964 0.5453 0.022 Uiso 1 1 calc R U . . .
H10B H 0.5636 0.8369 0.4638 0.022 Uiso 1 1 calc R U . . .
C11 C 0.3809(2) 0.7921(2) 0.42224(18) 0.0167(3) Uani 1 1 d . . . . .
H11A H 0.3667 0.8466 0.3363 0.020 Uiso 1 1 calc R U . . .
H11B H 0.3658 0.7046 0.4164 0.020 Uiso 1 1 calc R U . . .
N4 N 0.26110(18) 0.88174(17) 0.52035(14) 0.0141(2) Uani 1 1 d . . . . .
N5 N 0.24802(18) 0.82273(17) 0.64147(15) 0.0152(3) Uani 1 1 d . . . . .
N6 N 0.14702(18) 0.92572(16) 0.71530(14) 0.0133(2) Uani 1 1 d . . . . .
C12 C 0.1669(2) 1.02718(19) 0.51417(16) 0.0132(3) Uani 1 1 d . . . . .
C13 C 0.1354(2) 1.1366(2) 0.41328(17) 0.0171(3) Uani 1 1 d . . . . .
H13A H 0.1852 1.1173 0.3273 0.020 Uiso 1 1 calc R U . . .
C14 C 0.0280(2) 1.2735(2) 0.44656(19) 0.0191(3) Uani 1 1 d . . . . .
H14A H 0.0025 1.3510 0.3814 0.023 Uiso 1 1 calc R U . . .
C15 C -0.0460(2) 1.3024(2) 0.57547(19) 0.0177(3) Uani 1 1 d . . . . .
H15A H -0.1184 1.3988 0.5942 0.021 Uiso 1 1 calc R U . . .
C16 C -0.0155(2) 1.19467(19) 0.67379(17) 0.0145(3) Uani 1 1 d . . . . .
H16A H -0.0655 1.2141 0.7597 0.017 Uiso 1 1 calc R U . . .
C17 C 0.09282(19) 1.05484(18) 0.64073(16) 0.0118(2) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N1 2.0432(15) . ?
Cu1 N6 2.0540(15) 2_666 ?
Cu1 I1 2.6336(3) . ?
Cu1 I1 2.6669(3) 2_755 ?
Cu1 Cu1 2.9284(5) 2_755 ?
I1 Cu1 2.6669(3) 2_755 ?
N1 N2 1.315(2) . ?
N1 C1 1.379(2) . ?
N2 N3 1.345(2) . ?
N3 C6 1.361(2) . ?
N3 C7 1.461(2) . ?
C1 C6 1.398(2) . ?
C1 C2 1.406(2) . ?
C2 C3 1.383(2) . ?
C2 H2A 0.9500 . ?
C3 C4 1.416(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.376(3) . ?
C4 H4A 0.9500 . ?
C5 C6 1.403(2) . ?
C5 H5A 0.9500 . ?
C7 C8 1.525(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.523(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.531(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.525(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 N4 1.465(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
N4 N5 1.346(2) . ?
N4 C12 1.364(2) . ?
N5 N6 1.312(2) . ?
N6 C17 1.379(2) . ?
N6 Cu1 2.0540(15) 2_666 ?
C12 C17 1.400(2) . ?
C12 C13 1.404(2) . ?
C13 C14 1.376(3) . ?
C13 H13A 0.9500 . ?
C14 C15 1.423(3) . ?
C14 H14A 0.9500 . ?
C15 C16 1.376(3) . ?
C15 H15A 0.9500 . ?
C16 C17 1.401(2) . ?
C16 H16A 0.9500 . ?

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 N6 107.20(6) . 2_666 ?
N1 Cu1 I1 112.81(4) . . ?
N6 Cu1 I1 109.44(4) 2_666 . ?
N1 Cu1 I1 107.30(4) . 2_755 ?
N6 Cu1 I1 106.84(4) 2_666 2_755 ?
I1 Cu1 I1 112.929(9) . 2_755 ?
N1 Cu1 Cu1 128.28(4) . 2_755 ?
N6 Cu1 Cu1 124.27(4) 2_666 2_755 ?
I1 Cu1 Cu1 57.008(8) . 2_755 ?
I1 Cu1 Cu1 55.921(8) 2_755 2_755 ?
Cu1 I1 Cu1 67.070(9) . 2_755 ?
N2 N1 C1 108.75(14) . . ?
N2 N1 Cu1 118.57(11) . . ?
C1 N1 Cu1 132.66(12) . . ?
N1 N2 N3 108.42(14) . . ?
N2 N3 C6 110.65(14) . . ?
N2 N3 C7 122.11(14) . . ?
C6 N3 C7 127.15(14) . . ?
N1 C1 C6 107.59(14) . . ?
N1 C1 C2 131.68(15) . . ?
C6 C1 C2 120.71(15) . . ?
C3 C2 C1 116.28(15) . . ?
C3 C2 H2A 121.9 . . ?
C1 C2 H2A 121.9 . . ?
C2 C3 C4 122.23(16) . . ?
C2 C3 H3A 118.9 . . ?
C4 C3 H3A 118.9 . . ?
C5 C4 C3 122.06(16) . . ?
C5 C4 H4A 119.0 . . ?
C3 C4 H4A 119.0 . . ?
C4 C5 C6 115.52(16) . . ?
C4 C5 H5A 122.2 . . ?
C6 C5 H5A 122.2 . . ?
N3 C6 C1 104.59(14) . . ?
N3 C6 C5 132.21(16) . . ?
C1 C6 C5 123.19(16) . . ?
N3 C7 C8 112.24(14) . . ?
N3 C7 H7A 109.2 . . ?
C8 C7 H7A 109.2 . . ?
N3 C7 H7B 109.2 . . ?
C8 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
C9 C8 C7 112.82(14) . . ?
C9 C8 H8A 109.0 . . ?
C7 C8 H8A 109.0 . . ?
C9 C8 H8B 109.0 . . ?
C7 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
C8 C9 C10 113.57(15) . . ?
C8 C9 H9A 108.9 . . ?
C10 C9 H9A 108.9 . . ?
C8 C9 H9B 108.9 . . ?
C10 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
C11 C10 C9 113.53(15) . . ?
C11 C10 H10A 108.9 . . ?
C9 C10 H10A 108.9 . . ?
C11 C10 H10B 108.9 . . ?
C9 C10 H10B 108.9 . . ?
H10A C10 H10B 107.7 . . ?
N4 C11 C10 110.04(14) . . ?
N4 C11 H11A 109.7 . . ?
C10 C11 H11A 109.7 . . ?
N4 C11 H11B 109.7 . . ?
C10 C11 H11B 109.7 . . ?
H11A C11 H11B 108.2 . . ?
N5 N4 C12 110.83(14) . . ?
N5 N4 C11 119.24(15) . . ?
C12 N4 C11 129.45(15) . . ?
N6 N5 N4 108.45(14) . . ?
N5 N6 C17 108.65(14) . . ?
N5 N6 Cu1 122.37(12) . 2_666 ?
C17 N6 Cu1 128.97(11) . 2_666 ?
N4 C12 C17 104.11(15) . . ?
N4 C12 C13 133.64(16) . . ?
C17 C12 C13 122.24(16) . . ?
C14 C13 C12 115.94(16) . . ?
C14 C13 H13A 122.0 . . ?
C12 C13 H13A 122.0 . . ?
C13 C14 C15 122.01(17) . . ?
C13 C14 H14A 119.0 . . ?
C15 C14 H14A 119.0 . . ?
C16 C15 C14 121.83(17) . . ?
C16 C15 H15A 119.1 . . ?
C14 C15 H15A 119.1 . . ?
C15 C16 C17 116.59(16) . . ?
C15 C16 H16A 121.7 . . ?
C17 C16 H16A 121.7 . . ?
N6 C17 C12 107.96(14) . . ?
N6 C17 C16 130.66(15) . . ?
C12 C17 C16 121.39(15) . . ?

_refine_diff_density_max         1.420
_refine_diff_density_min         -1.073
_refine_diff_density_rms         0.256

####################################################################### 
# 
# 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_yf3-166c_a
_database_code_depnum_ccdc_archive 'CCDC 1888943'
loop_
_audit_author_name
_audit_author_address
'Simon J. Teat'
;Advanced Light Source
United States of America
;
_audit_update_record             
;
2019-01-05 deposited with the CCDC.	2019-04-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H15 Cu I N5'
_chemical_formula_weight         467.77

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0034 0.0017
'XDISP Program in WinGX S.Brennan & P.L.Cowan Rev.Sci.Instrum.63,850 1992'
H H 0.0000 0.0000
'XDISP Program in WinGX S.Brennan & P.L.Cowan Rev.Sci.Instrum.63,850 1992'
N N 0.0065 0.0035
'XDISP Program in WinGX S.Brennan & P.L.Cowan Rev.Sci.Instrum.63,850 1992'
Cu Cu 0.3203 1.3289
'XDISP Program in WinGX S.Brennan & P.L.Cowan Rev.Sci.Instrum.63,850 1992'
I I -0.3993 1.9038
'XDISP Program in WinGX S.Brennan & P.L.Cowan Rev.Sci.Instrum.63,850 1992'

_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                   8.5197(3)
_cell_length_b                   9.4963(3)
_cell_length_c                   10.5529(4)
_cell_angle_alpha                85.8689(12)
_cell_angle_beta                 77.7990(12)
_cell_angle_gamma                71.5887(12)
_cell_volume                     791.78(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9948
_cell_measurement_theta_min      2.9251
_cell_measurement_theta_max      31.3856

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.962
_exptl_crystal_F_000             456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.050
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    3.542
_shelx_estimated_absorpt_T_min   0.843
_shelx_estimated_absorpt_T_max   0.965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.859
_exptl_absorpt_correction_T_max  0.965
_exptl_absorpt_process_details   'SADABS 2016/2 Bruker AXS Madison WI USA'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.7288
_diffrn_radiation_type           synchrotron
_diffrn_source                   'Advanced Light Source beamline 12.2.1'
_diffrn_measurement_device_type  'Bruker D8 with PHOTONII detector'
_diffrn_measurement_method       'ω/θ shutterless scans'
_diffrn_detector_area_resol_mean 7.39
_diffrn_reflns_number            27271
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.025
_diffrn_reflns_theta_max         31.407
_diffrn_reflns_theta_full        25.930
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4843
_reflns_number_gt                4521
_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 APEX 3'
_computing_cell_refinement       'Bruker SAINT v8.38a'
_computing_data_reduction        'Bruker SAINT v8.38a'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL & local programs'
_refine_special_details          
;
 All non-hydrogen atoms were refined anisotropically. Hydrogen atoms were found
 in the difference map and allowed to refine freely.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0150P)²+0.8965P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'Dual space'
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4843
_refine_ls_number_parameters     268
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0257
_refine_ls_R_factor_gt           0.0228
_refine_ls_wR_factor_ref         0.0496
_refine_ls_wR_factor_gt          0.0483
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_restrained_S_all      1.100
_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 0.08551(3) 1.04906(3) 0.88004(2) 0.01403(6) Uani 1 1 d . . . . .
I1 I -0.21807(2) 1.02436(2) 0.90671(2) 0.01281(4) Uani 1 1 d . . . . .
N1 N 0.2774(2) 0.93351(18) 0.73857(16) 0.0135(3) Uani 1 1 d . . . . .
C1 C 0.4373(2) 0.9160(2) 0.73488(19) 0.0132(3) Uani 1 1 d . . . . .
N2 N 0.5394(2) 0.84355(19) 0.62711(16) 0.0138(3) Uani 1 1 d . . . . .
C2 C 0.4381(2) 0.8112(2) 0.55493(19) 0.0138(4) Uani 1 1 d . . . . .
C3 C 0.4738(3) 0.7406(3) 0.4361(2) 0.0194(4) Uani 1 1 d . . . . .
C4 C 0.3365(3) 0.7332(3) 0.3900(2) 0.0212(4) Uani 1 1 d . . . . .
C5 C 0.1703(3) 0.7931(3) 0.4588(2) 0.0190(4) Uani 1 1 d . . . . .
C6 C 0.1359(3) 0.8613(2) 0.57752(19) 0.0156(4) Uani 1 1 d . . . . .
C7 C 0.2731(2) 0.8695(2) 0.62538(18) 0.0126(3) Uani 1 1 d . . . . .
C8 C 0.7225(3) 0.8136(2) 0.5913(2) 0.0173(4) Uani 1 1 d . . . . .
C9 C 0.8215(3) 0.6564(2) 0.6260(2) 0.0167(4) Uani 1 1 d . . . . .
C10 C 0.7879(3) 0.6279(2) 0.7720(2) 0.0160(4) Uani 1 1 d . . . . .
N3 N 0.9210(2) 0.50240(18) 0.80877(16) 0.0136(3) Uani 1 1 d . . . . .
N4 N 0.9140(2) 0.36205(19) 0.81155(17) 0.0168(3) Uani 1 1 d . . . . .
N5 N 1.0529(2) 0.27084(18) 0.84146(16) 0.0139(3) Uani 1 1 d . . . . .
C11 C 1.1551(2) 0.3532(2) 0.85758(18) 0.0122(3) Uani 1 1 d . . . . .
C12 C 1.3152(2) 0.3105(2) 0.88953(18) 0.0141(4) Uani 1 1 d . . . . .
C13 C 1.3830(3) 0.4219(2) 0.89986(19) 0.0160(4) Uani 1 1 d . . . . .
C14 C 1.2952(3) 0.5730(2) 0.8803(2) 0.0166(4) Uani 1 1 d . . . . .
C15 C 1.1381(3) 0.6168(2) 0.84831(19) 0.0153(4) Uani 1 1 d . . . . .
C16 C 1.0705(2) 0.5029(2) 0.83664(18) 0.0127(3) Uani 1 1 d . . . . .
H1 H 0.475(4) 0.946(3) 0.789(3) 0.031(8) Uiso 1 1 d . . . . .
H3 H 0.584(4) 0.703(3) 0.388(3) 0.039(9) Uiso 1 1 d . . . . .
H4 H 0.358(3) 0.689(3) 0.305(3) 0.025(7) Uiso 1 1 d . . . . .
H5 H 0.076(3) 0.790(3) 0.420(3) 0.025(7) Uiso 1 1 d . . . . .
H6 H 0.023(3) 0.905(3) 0.627(2) 0.014(6) Uiso 1 1 d . . . . .
H8A H 0.752(3) 0.838(3) 0.495(2) 0.008(5) Uiso 1 1 d . . . . .
H8B H 0.745(3) 0.881(3) 0.633(2) 0.017(6) Uiso 1 1 d . . . . .
H9A H 0.936(3) 0.645(3) 0.596(2) 0.018(6) Uiso 1 1 d . . . . .
H9B H 0.791(3) 0.586(3) 0.581(3) 0.021(7) Uiso 1 1 d . . . . .
H10A H 0.684(3) 0.603(3) 0.801(3) 0.021(7) Uiso 1 1 d . . . . .
H10B H 0.786(3) 0.712(3) 0.819(3) 0.023(7) Uiso 1 1 d . . . . .
H12 H 1.375(3) 0.210(3) 0.903(2) 0.018(6) Uiso 1 1 d . . . . .
H13 H 1.493(3) 0.399(3) 0.920(2) 0.015(6) Uiso 1 1 d . . . . .
H14 H 1.347(3) 0.647(3) 0.890(3) 0.022(7) Uiso 1 1 d . . . . .
H15 H 1.074(3) 0.716(3) 0.838(2) 0.015(6) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N1 2.0436(17) . ?
Cu1 N5 2.0574(17) 1_465 ?
Cu1 I1 2.6248(3) . ?
Cu1 I1 2.6789(3) 2_577 ?
Cu1 Cu1 2.8914(5) 2_577 ?
N1 C1 1.312(2) . ?
N1 C7 1.391(2) . ?
C1 N2 1.356(3) . ?
C1 H1 0.82(3) . ?
N2 C2 1.378(3) . ?
N2 C8 1.464(3) . ?
C2 C3 1.395(3) . ?
C2 C7 1.401(3) . ?
C3 C4 1.381(3) . ?
C3 H3 0.94(3) . ?
C4 C5 1.404(3) . ?
C4 H4 0.98(3) . ?
C5 C6 1.385(3) . ?
C5 H5 0.98(3) . ?
C6 C7 1.393(3) . ?
C6 H6 0.97(2) . ?
C8 C9 1.526(3) . ?
C8 H8A 1.02(2) . ?
C8 H8B 0.89(3) . ?
C9 C10 1.527(3) . ?
C9 H9A 0.93(3) . ?
C9 H9B 0.97(3) . ?
C10 N3 1.457(2) . ?
C10 H10A 0.97(3) . ?
C10 H10B 0.96(3) . ?
N3 N4 1.351(2) . ?
N3 C16 1.368(2) . ?
N4 N5 1.312(2) . ?
N5 C11 1.383(2) . ?
C11 C12 1.401(3) . ?
C11 C16 1.402(3) . ?
C12 C13 1.377(3) . ?
C12 H12 0.94(3) . ?
C13 C14 1.416(3) . ?
C13 H13 0.96(3) . ?
C14 C15 1.378(3) . ?
C14 H14 0.96(3) . ?
C15 C16 1.399(3) . ?
C15 H15 0.94(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 N5 106.89(7) . 1_465 ?
N1 Cu1 I1 120.21(5) . . ?
N5 Cu1 I1 104.30(5) 1_465 . ?
N1 Cu1 I1 102.46(5) . 2_577 ?
N5 Cu1 I1 108.55(5) 1_465 2_577 ?
I1 Cu1 I1 113.937(10) . 2_577 ?
N1 Cu1 Cu1 131.06(5) . 2_577 ?
N5 Cu1 Cu1 121.26(5) 1_465 2_577 ?
I1 Cu1 Cu1 57.870(9) . 2_577 ?
I1 Cu1 Cu1 56.068(9) 2_577 2_577 ?
Cu1 I1 Cu1 66.061(10) . 2_577 ?
C1 N1 C7 105.55(16) . . ?
C1 N1 Cu1 123.71(14) . . ?
C7 N1 Cu1 130.56(13) . . ?
N1 C1 N2 112.59(18) . . ?
N1 C1 H1 126(2) . . ?
N2 C1 H1 121(2) . . ?
C1 N2 C2 107.44(16) . . ?
C1 N2 C8 125.85(17) . . ?
C2 N2 C8 126.62(17) . . ?
N2 C2 C3 132.43(19) . . ?
N2 C2 C7 105.22(17) . . ?
C3 C2 C7 122.33(18) . . ?
C4 C3 C2 116.22(19) . . ?
C4 C3 H3 121.0(19) . . ?
C2 C3 H3 122.7(19) . . ?
C3 C4 C5 122.0(2) . . ?
C3 C4 H4 117.7(16) . . ?
C5 C4 H4 120.2(16) . . ?
C6 C5 C4 121.5(2) . . ?
C6 C5 H5 119.3(16) . . ?
C4 C5 H5 119.2(16) . . ?
C5 C6 C7 117.21(19) . . ?
C5 C6 H6 123.6(15) . . ?
C7 C6 H6 119.2(15) . . ?
N1 C7 C6 130.03(18) . . ?
N1 C7 C2 109.19(17) . . ?
C6 C7 C2 120.75(18) . . ?
N2 C8 C9 113.11(17) . . ?
N2 C8 H8A 108.0(13) . . ?
C9 C8 H8A 113.1(13) . . ?
N2 C8 H8B 105.7(17) . . ?
C9 C8 H8B 111.3(17) . . ?
H8A C8 H8B 105(2) . . ?
C8 C9 C10 111.91(17) . . ?
C8 C9 H9A 107.7(16) . . ?
C10 C9 H9A 109.5(16) . . ?
C8 C9 H9B 109.1(16) . . ?
C10 C9 H9B 110.1(16) . . ?
H9A C9 H9B 108(2) . . ?
N3 C10 C9 111.43(16) . . ?
N3 C10 H10A 105.7(16) . . ?
C9 C10 H10A 111.7(16) . . ?
N3 C10 H10B 106.3(16) . . ?
C9 C10 H10B 110.9(16) . . ?
H10A C10 H10B 111(2) . . ?
N4 N3 C16 110.06(16) . . ?
N4 N3 C10 121.90(17) . . ?
C16 N3 C10 127.91(17) . . ?
N5 N4 N3 109.21(16) . . ?
N4 N5 C11 108.26(16) . . ?
N4 N5 Cu1 122.90(13) . 1_645 ?
C11 N5 Cu1 128.34(13) . 1_645 ?
N5 C11 C12 131.28(18) . . ?
N5 C11 C16 107.98(17) . . ?
C12 C11 C16 120.74(18) . . ?
C13 C12 C11 116.86(18) . . ?
C13 C12 H12 120.7(16) . . ?
C11 C12 H12 122.5(16) . . ?
C12 C13 C14 121.88(19) . . ?
C12 C13 H13 120.6(15) . . ?
C14 C13 H13 117.5(15) . . ?
C15 C14 C13 121.95(19) . . ?
C15 C14 H14 119.4(16) . . ?
C13 C14 H14 118.7(16) . . ?
C14 C15 C16 115.94(18) . . ?
C14 C15 H15 124.2(15) . . ?
C16 C15 H15 119.7(15) . . ?
N3 C16 C15 132.89(18) . . ?
N3 C16 C11 104.48(17) . . ?
C15 C16 C11 122.61(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
C7 N1 C1 N2 -0.4(2) . . . . ?
Cu1 N1 C1 N2 -175.91(13) . . . . ?
N1 C1 N2 C2 -0.1(2) . . . . ?
N1 C1 N2 C8 176.68(18) . . . . ?
C1 N2 C2 C3 179.2(2) . . . . ?
C8 N2 C2 C3 2.4(4) . . . . ?
C1 N2 C2 C7 0.5(2) . . . . ?
C8 N2 C2 C7 -176.19(18) . . . . ?
N2 C2 C3 C4 -177.3(2) . . . . ?
C7 C2 C3 C4 1.1(3) . . . . ?
C2 C3 C4 C5 -0.1(3) . . . . ?
C3 C4 C5 C6 -0.7(4) . . . . ?
C4 C5 C6 C7 0.6(3) . . . . ?
C1 N1 C7 C6 -177.4(2) . . . . ?
Cu1 N1 C7 C6 -2.4(3) . . . . ?
C1 N1 C7 C2 0.8(2) . . . . ?
Cu1 N1 C7 C2 175.82(13) . . . . ?
C5 C6 C7 N1 178.3(2) . . . . ?
C5 C6 C7 C2 0.3(3) . . . . ?
N2 C2 C7 N1 -0.8(2) . . . . ?
C3 C2 C7 N1 -179.60(19) . . . . ?
N2 C2 C7 C6 177.59(18) . . . . ?
C3 C2 C7 C6 -1.2(3) . . . . ?
C1 N2 C8 C9 99.1(2) . . . . ?
C2 N2 C8 C9 -84.8(2) . . . . ?
N2 C8 C9 C10 -62.5(2) . . . . ?
C8 C9 C10 N3 -160.08(17) . . . . ?
C9 C10 N3 N4 -89.3(2) . . . . ?
C9 C10 N3 C16 86.3(2) . . . . ?
C16 N3 N4 N5 0.6(2) . . . . ?
C10 N3 N4 N5 176.92(17) . . . . ?
N3 N4 N5 C11 -0.6(2) . . . . ?
N3 N4 N5 Cu1 171.88(12) . . . 1_645 ?
N4 N5 C11 C12 -180.0(2) . . . . ?
Cu1 N5 C11 C12 8.1(3) 1_645 . . . ?
N4 N5 C11 C16 0.4(2) . . . . ?
Cu1 N5 C11 C16 -171.55(13) 1_645 . . . ?
N5 C11 C12 C13 -179.2(2) . . . . ?
C16 C11 C12 C13 0.4(3) . . . . ?
C11 C12 C13 C14 0.5(3) . . . . ?
C12 C13 C14 C15 -0.8(3) . . . . ?
C13 C14 C15 C16 0.1(3) . . . . ?
N4 N3 C16 C15 -178.7(2) . . . . ?
C10 N3 C16 C15 5.2(3) . . . . ?
N4 N3 C16 C11 -0.3(2) . . . . ?
C10 N3 C16 C11 -176.36(18) . . . . ?
C14 C15 C16 N3 179.0(2) . . . . ?
C14 C15 C16 C11 0.8(3) . . . . ?
N5 C11 C16 N3 0.0(2) . . . . ?
C12 C11 C16 N3 -179.72(17) . . . . ?
N5 C11 C16 C15 178.57(18) . . . . ?
C12 C11 C16 C15 -1.1(3) . . . . ?

_refine_diff_density_max         0.486
_refine_diff_density_min         -0.801
_refine_diff_density_rms         0.104

