# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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. 
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data_az329a
_database_code_depnum_ccdc_archive 'CCDC 1563140'
_audit_update_record             
;
2017-07-19 deposited with the CCDC.
2018-06-21 downloaded from the CCDC.
;
#==============================================================================

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H60 Cl2 Cu2 F12 N14 Sb2'
_chemical_formula_weight         1358.46

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   12.210(2)
_cell_length_b                   17.004(3)
_cell_length_c                   12.728(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.36(3)
_cell_angle_gamma                90
_cell_volume                     2638.0(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    120
_cell_measurement_reflns_used    7716
_cell_measurement_theta_min      2.00
_cell_measurement_theta_max      30.06

_exptl_crystal_description       'box shaped'
_exptl_crystal_colour            'dark green'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.710
_exptl_crystal_F_000             1352
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    1.994
_shelx_estimated_absorpt_T_min   0.542
_shelx_estimated_absorpt_T_max   0.636
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.542
_exptl_absorpt_correction_T_max  0.636
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'NONIUS KAPPA CCD'
_diffrn_measurement_method       'O-Scan    '
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            43282
_diffrn_reflns_av_unetI/netI     0.0557
_diffrn_reflns_av_R_equivalents  0.0637
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.001
_diffrn_reflns_theta_max         30.060
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7716
_reflns_number_gt                5346
_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       'COLLECT (Bruker AXS, 1997-2009)'
_computing_cell_refinement       'DENZO/SKALEPACK (Bruker AXS, 1997-2009)'
_computing_data_reduction        'DENZO/SKALEPACK (Bruker AXS, 1997-2009)'
_computing_structure_solution    'SHELXS-2016 (sheldrick 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'XPMA (Zsolnai, Huttner, 1994)'
_computing_publication_material  'SHELXL-2016/6 (Sheldrick, 2016)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0496P)²+0.7129P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7716
_refine_ls_number_parameters     315
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0759
_refine_ls_R_factor_gt           0.0396
_refine_ls_wR_factor_ref         0.1003
_refine_ls_wR_factor_gt          0.0861
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_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
Sb1 Sb 0.69662(2) 0.02603(2) 0.25957(2) 0.02862(7) Uani 1 1 d . . . . .
Cu1 Cu 0.61877(3) 0.33585(2) 0.70293(3) 0.02219(9) Uani 1 1 d . . . . .
Cl1 Cl 0.75017(6) 0.24689(4) 0.66603(6) 0.02942(17) Uani 1 1 d . . . . .
F1 F 0.72447(19) 0.12096(14) 0.3291(2) 0.0683(8) Uani 1 1 d . . . . .
F2 F 0.7894(3) -0.02568(19) 0.3577(2) 0.0908(11) Uani 1 1 d . . . . .
F3 F 0.66426(18) -0.06910(12) 0.19256(18) 0.0525(6) Uani 1 1 d . . . . .
F4 F 0.6028(2) 0.07671(15) 0.16211(18) 0.0660(7) Uani 1 1 d . . . . .
F5 F 0.8142(2) 0.04166(16) 0.1760(2) 0.0758(8) Uani 1 1 d . . . . .
F6 F 0.5799(2) 0.01153(14) 0.34574(17) 0.0566(6) Uani 1 1 d . . . . .
N1 N 0.51780(19) 0.34435(13) 0.56575(17) 0.0199(5) Uani 1 1 d . . . . .
N2 N 0.5496(2) 0.27934(14) 0.40707(19) 0.0277(6) Uani 1 1 d . . . . .
N3 N 0.4415(2) 0.22183(15) 0.5295(2) 0.0319(6) Uani 1 1 d . . . . .
N4 N 0.63168(19) 0.45067(13) 0.66857(17) 0.0196(5) Uani 1 1 d . . . . .
N5 N 0.8032(2) 0.51038(14) 0.67560(19) 0.0244(5) Uani 1 1 d . . . . .
N6 N 0.6911(2) 0.52415(14) 0.81682(18) 0.0277(6) Uani 1 1 d . . . . .
N7 N 0.5694(2) 0.30595(14) 0.84394(18) 0.0249(5) Uani 1 1 d . . . . .
C1 C 0.5051(2) 0.41840(15) 0.5275(2) 0.0182(5) Uani 1 1 d . . . . .
C2 C 0.5686(2) 0.47890(15) 0.5892(2) 0.0182(5) Uani 1 1 d . . . . .
C3 C 0.5597(2) 0.55860(16) 0.5599(2) 0.0198(6) Uani 1 1 d . . . . .
H3 H 0.598064 0.596408 0.600002 0.024 Uiso 1 1 calc R U . . .
C4 C 0.5009(2) 0.28271(15) 0.4993(2) 0.0233(6) Uani 1 1 d . . . . .
C5 C 0.6468(3) 0.32702(19) 0.3888(2) 0.0331(7) Uani 1 1 d . . . . .
H5A H 0.624272 0.376142 0.357208 0.050 Uiso 1 1 calc R U . . .
H5B H 0.692723 0.299325 0.342584 0.050 Uiso 1 1 calc R U . . .
H5C H 0.686857 0.336819 0.454636 0.050 Uiso 1 1 calc R U . . .
C6 C 0.4966(3) 0.2440(2) 0.3124(3) 0.0447(9) Uani 1 1 d . . . . .
H6A H 0.539276 0.200053 0.290835 0.067 Uiso 1 1 calc R U . . .
H6B H 0.491298 0.282347 0.256956 0.067 Uiso 1 1 calc R U . . .
H6C H 0.424397 0.226365 0.327165 0.067 Uiso 1 1 calc R U . . .
C7 C 0.3742(3) 0.2291(2) 0.6210(3) 0.0444(9) Uani 1 1 d . . . . .
H7A H 0.415794 0.211869 0.683078 0.067 Uiso 1 1 calc R U . . .
H7B H 0.309653 0.197226 0.610356 0.067 Uiso 1 1 calc R U . . .
H7C H 0.353225 0.283087 0.629283 0.067 Uiso 1 1 calc R U . . .
C8 C 0.4617(3) 0.14172(19) 0.4944(3) 0.0509(10) Uani 1 1 d . . . . .
H8A H 0.402687 0.125263 0.446245 0.076 Uiso 1 1 calc R U . . .
H8B H 0.466401 0.107093 0.554033 0.076 Uiso 1 1 calc R U . . .
H8C H 0.529447 0.140121 0.459714 0.076 Uiso 1 1 calc R U . . .
C9 C 0.7093(2) 0.49812(16) 0.7213(2) 0.0217(6) Uani 1 1 d . . . . .
C10 C 0.8310(3) 0.46354(19) 0.5840(2) 0.0320(7) Uani 1 1 d . . . . .
H10A H 0.805322 0.410622 0.591850 0.048 Uiso 1 1 calc R U . . .
H10B H 0.909118 0.463211 0.578876 0.048 Uiso 1 1 calc R U . . .
H10C H 0.796664 0.486160 0.521237 0.048 Uiso 1 1 calc R U . . .
C11 C 0.8736(3) 0.57898(19) 0.6978(3) 0.0397(8) Uani 1 1 d . . . . .
H11A H 0.834587 0.617074 0.736872 0.060 Uiso 1 1 calc R U . . .
H11B H 0.893774 0.601879 0.632753 0.060 Uiso 1 1 calc R U . . .
H11C H 0.938560 0.562906 0.738326 0.060 Uiso 1 1 calc R U . . .
C12 C 0.5796(3) 0.5276(2) 0.8530(3) 0.0401(9) Uani 1 1 d . . . . .
H12A H 0.527670 0.521145 0.793962 0.060 Uiso 1 1 calc R U . . .
H12B H 0.568103 0.577518 0.885675 0.060 Uiso 1 1 calc R U . . .
H12C H 0.569806 0.486233 0.902947 0.060 Uiso 1 1 calc R U . . .
C13 C 0.7788(3) 0.5394(2) 0.8978(3) 0.0413(9) Uani 1 1 d . . . . .
H13A H 0.845713 0.515732 0.877263 0.062 Uiso 1 1 calc R U . . .
H13B H 0.759148 0.517269 0.963461 0.062 Uiso 1 1 calc R U . . .
H13C H 0.789111 0.595077 0.905635 0.062 Uiso 1 1 calc R U . . .
C14 C 0.6330(3) 0.26401(18) 0.9118(2) 0.0289(7) Uani 1 1 d . . . . .
H14 H 0.706163 0.256586 0.897709 0.035 Uiso 1 1 calc R U . . .
C15 C 0.5951(3) 0.2310(2) 1.0023(2) 0.0356(8) Uani 1 1 d . . . . .
H15 H 0.641887 0.202006 1.047721 0.043 Uiso 1 1 calc R U . . .
C16 C 0.4875(3) 0.24168(19) 1.0238(2) 0.0342(7) Uani 1 1 d . . . . .
H16 H 0.459658 0.219047 1.083148 0.041 Uiso 1 1 calc R U . . .
C17 C 0.4207(3) 0.28668(19) 0.9558(2) 0.0320(7) Uani 1 1 d . . . . .
H17 H 0.347608 0.295534 0.968983 0.038 Uiso 1 1 calc R U . . .
C18 C 0.4651(3) 0.31798(19) 0.8681(2) 0.0310(7) Uani 1 1 d . . . . .
H18 H 0.420616 0.349090 0.823266 0.037 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
Sb1 F4 1.851(2) . ?
Sb1 F5 1.855(2) . ?
Sb1 F2 1.858(3) . ?
Sb1 F3 1.860(2) . ?
Sb1 F1 1.862(2) . ?
Sb1 F6 1.865(2) . ?
Cu1 N7 1.992(2) . ?
Cu1 N4 2.009(2) . ?
Cu1 N1 2.083(2) . ?
Cu1 Cl1 2.2740(8) . ?
N1 C4 1.355(3) . ?
N1 C1 1.356(3) . ?
N2 C4 1.348(4) . ?
N2 C6 1.464(4) . ?
N2 C5 1.467(4) . ?
N3 C4 1.334(4) . ?
N3 C8 1.459(4) . ?
N3 C7 1.469(4) . ?
N4 C2 1.324(3) . ?
N4 C9 1.387(4) . ?
N5 C9 1.332(4) . ?
N5 C11 1.467(4) . ?
N5 C10 1.468(4) . ?
N6 C9 1.325(4) . ?
N6 C12 1.464(4) . ?
N6 C13 1.465(4) . ?
N7 C14 1.333(4) . ?
N7 C18 1.343(4) . ?
C1 C3 1.383(4) 3_666 ?
C1 C2 1.485(4) . ?
C2 C3 1.408(4) . ?
C3 H3 0.9300 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.386(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.370(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.384(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.376(4) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?

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
F4 Sb1 F5 91.03(13) . . ?
F4 Sb1 F2 179.31(14) . . ?
F5 Sb1 F2 89.52(14) . . ?
F4 Sb1 F3 89.49(11) . . ?
F5 Sb1 F3 90.70(10) . . ?
F2 Sb1 F3 90.08(12) . . ?
F4 Sb1 F1 90.20(12) . . ?
F5 Sb1 F1 91.29(11) . . ?
F2 Sb1 F1 90.20(13) . . ?
F3 Sb1 F1 177.99(10) . . ?
F4 Sb1 F6 89.52(12) . . ?
F5 Sb1 F6 178.84(11) . . ?
F2 Sb1 F6 89.93(13) . . ?
F3 Sb1 F6 90.32(10) . . ?
F1 Sb1 F6 87.69(10) . . ?
N7 Cu1 N4 118.41(10) . . ?
N7 Cu1 N1 125.28(10) . . ?
N4 Cu1 N1 78.47(9) . . ?
N7 Cu1 Cl1 105.70(8) . . ?
N4 Cu1 Cl1 122.42(7) . . ?
N1 Cu1 Cl1 105.26(7) . . ?
C4 N1 C1 118.9(2) . . ?
C4 N1 Cu1 122.05(18) . . ?
C1 N1 Cu1 114.55(18) . . ?
C4 N2 C6 122.6(3) . . ?
C4 N2 C5 121.1(2) . . ?
C6 N2 C5 114.8(3) . . ?
C4 N3 C8 122.1(3) . . ?
C4 N3 C7 120.1(3) . . ?
C8 N3 C7 115.8(3) . . ?
C2 N4 C9 120.5(2) . . ?
C2 N4 Cu1 117.97(19) . . ?
C9 N4 Cu1 121.34(18) . . ?
C9 N5 C11 123.4(3) . . ?
C9 N5 C10 120.4(3) . . ?
C11 N5 C10 115.1(3) . . ?
C9 N6 C12 120.7(3) . . ?
C9 N6 C13 123.3(3) . . ?
C12 N6 C13 115.3(3) . . ?
C14 N7 C18 117.2(3) . . ?
C14 N7 Cu1 121.6(2) . . ?
C18 N7 Cu1 120.6(2) . . ?
N1 C1 C3 126.8(3) . 3_666 ?
N1 C1 C2 114.1(2) . . ?
C3 C1 C2 119.1(2) 3_666 . ?
N4 C2 C3 125.7(3) . . ?
N4 C2 C1 114.5(2) . . ?
C3 C2 C1 119.8(2) . . ?
C1 C3 C2 121.1(3) 3_666 . ?
C1 C3 H3 119.4 3_666 . ?
C2 C3 H3 119.4 . . ?
N3 C4 N2 119.6(3) . . ?
N3 C4 N1 119.1(3) . . ?
N2 C4 N1 121.2(3) . . ?
N2 C5 H5A 109.5 . . ?
N2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N2 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N3 C7 H7A 109.5 . . ?
N3 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N3 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N3 C8 H8A 109.5 . . ?
N3 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N3 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N6 C9 N5 122.9(3) . . ?
N6 C9 N4 119.4(3) . . ?
N5 C9 N4 117.5(3) . . ?
N5 C10 H10A 109.5 . . ?
N5 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N5 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N5 C11 H11A 109.5 . . ?
N5 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N5 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N6 C12 H12A 109.5 . . ?
N6 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N6 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N6 C13 H13A 109.5 . . ?
N6 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N6 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N7 C14 C15 123.0(3) . . ?
N7 C14 H14 118.5 . . ?
C15 C14 H14 118.5 . . ?
C16 C15 C14 118.9(3) . . ?
C16 C15 H15 120.6 . . ?
C14 C15 H15 120.6 . . ?
C15 C16 C17 119.0(3) . . ?
C15 C16 H16 120.5 . . ?
C17 C16 H16 120.5 . . ?
C18 C17 C16 118.3(3) . . ?
C18 C17 H17 120.8 . . ?
C16 C17 H17 120.8 . . ?
N7 C18 C17 123.5(3) . . ?
N7 C18 H18 118.3 . . ?
C17 C18 H18 118.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 N1 C1 C3 25.4(4) . . . 3_666 ?
Cu1 N1 C1 C3 -177.8(2) . . . 3_666 ?
C4 N1 C1 C2 -155.0(2) . . . . ?
Cu1 N1 C1 C2 1.8(3) . . . . ?
C9 N4 C2 C3 -10.2(4) . . . . ?
Cu1 N4 C2 C3 174.1(2) . . . . ?
C9 N4 C2 C1 168.8(2) . . . . ?
Cu1 N4 C2 C1 -6.9(3) . . . . ?
N1 C1 C2 N4 3.1(3) . . . . ?
C3 C1 C2 N4 -177.2(2) 3_666 . . . ?
N1 C1 C2 C3 -177.8(2) . . . . ?
C3 C1 C2 C3 1.8(4) 3_666 . . . ?
N4 C2 C3 C1 177.1(3) . . . 3_666 ?
C1 C2 C3 C1 -1.8(4) . . . 3_666 ?
C8 N3 C4 N2 26.4(4) . . . . ?
C7 N3 C4 N2 -170.5(3) . . . . ?
C8 N3 C4 N1 -148.7(3) . . . . ?
C7 N3 C4 N1 14.4(4) . . . . ?
C6 N2 C4 N3 39.1(4) . . . . ?
C5 N2 C4 N3 -155.7(3) . . . . ?
C6 N2 C4 N1 -145.9(3) . . . . ?
C5 N2 C4 N1 19.3(4) . . . . ?
C1 N1 C4 N3 -134.6(3) . . . . ?
Cu1 N1 C4 N3 70.4(3) . . . . ?
C1 N1 C4 N2 50.4(4) . . . . ?
Cu1 N1 C4 N2 -104.6(3) . . . . ?
C12 N6 C9 N5 164.0(3) . . . . ?
C13 N6 C9 N5 -25.8(4) . . . . ?
C12 N6 C9 N4 -21.3(4) . . . . ?
C13 N6 C9 N4 148.9(3) . . . . ?
C11 N5 C9 N6 -29.0(4) . . . . ?
C10 N5 C9 N6 163.5(3) . . . . ?
C11 N5 C9 N4 156.2(3) . . . . ?
C10 N5 C9 N4 -11.3(4) . . . . ?
C2 N4 C9 N6 106.1(3) . . . . ?
Cu1 N4 C9 N6 -78.3(3) . . . . ?
C2 N4 C9 N5 -78.9(3) . . . . ?
Cu1 N4 C9 N5 96.7(3) . . . . ?
C18 N7 C14 C15 2.2(5) . . . . ?
Cu1 N7 C14 C15 -168.7(3) . . . . ?
N7 C14 C15 C16 -0.1(5) . . . . ?
C14 C15 C16 C17 -1.5(5) . . . . ?
C15 C16 C17 C18 0.9(5) . . . . ?
C14 N7 C18 C17 -2.8(5) . . . . ?
Cu1 N7 C18 C17 168.2(2) . . . . ?
C16 C17 C18 N7 1.3(5) . . . . ?

_refine_diff_density_max         1.017
_refine_diff_density_min         -0.720
_refine_diff_density_rms         0.114

####################################################################### 
# 
# 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_hi_az19
_database_code_depnum_ccdc_archive 'CCDC 1563142'
_audit_update_record             
;
2017-07-19 deposited with the CCDC.
2018-06-21 downloaded from the CCDC.
;
_audit_creation_date             2017-01-31

_audit_block_code                hi_az19
_audit_block_refno               2812

_audit_creation_method           
;
Olex2 1.2
(compiled Dec 12 2016 15:58:59 for OlexSys, GUI svn.r5292)
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         
'0.5(C52 H100 Cl4 Cu4 N24), 2(C7 H5 N), 2(F6 Sb)'
_chemical_formula_sum            'C40 H60 Cl2 Cu2 F12 N14 Sb2'
_chemical_properties_physical    'air-sensitive, moisture-sensitive'
_chemical_formula_weight         1406.50
_chemical_melting_point          ?
_exptl_crystal_description       plate
_exptl_crystal_colour            'dark yellow'
_diffrn_ambient_temperature      120(1)
_chemical_oxdiff_formula         'C40 H60 Cl2 Cu2 F12 N14 Sb2'
_chemical_oxdiff_usercomment     'hi_az327a, plate, dark yellow'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'x+1/2, -y, -z+1/2'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'-x-1/2, y, z-1/2'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.12549(13)
_cell_length_b                   22.2307(3)
_cell_length_c                   21.9849(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5437.48(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    33531
_cell_measurement_temperature    120(1)
_cell_measurement_theta_max      31.7510
_cell_measurement_theta_min      3.1730
_shelx_estimated_absorpt_T_max   0.920
_shelx_estimated_absorpt_T_min   0.760
_exptl_absorpt_coefficient_mu    1.938
_exptl_absorpt_correction_T_max  0.927
_exptl_absorpt_correction_T_min  0.787
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
 a multifaceted crystal model (Busing & Levy, 1957).
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_density_diffrn    1.718
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             2800
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-15 -6 0 0.0315
2 6 30 0.0607
-3 -7 -30 0.0714
15 5 -1 0.0428
-2 31 -3 0.0222
13 -3 -18 0.0704
-12 10 17 0.0554
2 -31 2 0.0200
15 -10 -2 0.0315
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.076
_exptl_crystal_size_min          0.044
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-14.9980 -6.0089 0.0002 0.1887 -0.5786 0.7619
1.9991 6.0108 29.9961 -0.2311 0.8372 0.4846
-2.9989 -7.0113 -29.9959 0.2628 -0.8752 -0.4333
14.9981 5.0087 -0.9998 -0.1555 0.5541 -0.7807
-2.0039 30.9942 -3.0088 -0.9848 -0.1853 0.0151
12.9993 -2.9974 -17.9964 0.1220 0.0505 -1.0077
-12.0003 9.9970 16.9946 -0.3437 -0.0440 0.9315
2.0039 -30.9946 2.0089 0.9861 0.1597 -0.0347
14.9884 -10.0073 -1.9901 0.3247 0.5432 -0.7868

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0706
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            176887
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.436
_diffrn_reflns_theta_min         2.605
_diffrn_ambient_environment      'perfluoro polyether oil / N~2~'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 7.9621
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -45.00  53.00   0.50   25.00    --   27.02 -38.00 -90.00  196
  2  ω    -20.00  69.00   0.50   25.00    --   27.02 -99.00  60.00  178
  3  ω      7.00  96.00   0.50   25.00    --   27.02  57.00   0.00  178
  4  ω     10.00  93.00   0.50   25.00    --   27.02-138.00 -29.00  166
  5  ω    -42.00  48.00   0.50   25.00    --   27.02 -57.00-150.00  180
  6  ω     -3.00  97.00   0.50   25.00    --   27.02  77.00-180.00  200
  7  ω    -42.00  48.00   0.50   25.00    --   27.02 -57.00 120.00  180
  8  ω     -3.00  97.00   0.50   25.00    --   27.02  77.00  60.00  200
  9  ω      7.00  96.00   0.50   25.00    --   27.02  57.00 -60.00  178
 10  ω    -49.00 -18.00   0.50   25.00    --    4.00 118.00 145.18   62
 11  ω     -4.00  25.00   0.50   25.00    --   27.02  79.00 -98.53   58
 12  ω      7.00  96.00   0.50   25.00    --   27.02  57.00 150.00  178
 13  ω    -20.00  69.00   0.50   25.00    --   27.02 -99.00-180.00  178
 14  ω     -5.00  24.00   0.50   25.00    --   27.02  80.00  32.15   58
 15  ω      7.00  96.00   0.50   25.00    --   27.02  57.00-150.00  178
 16  ω    -42.00  48.00   0.50   25.00    --   27.02 -57.00  60.00  180
 17  ω      7.00  86.00   0.50   25.00    --   27.02  57.00 -90.00  158
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Agilent SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0001936000
_diffrn_orient_matrix_UB_12      -0.0318889000
_diffrn_orient_matrix_UB_13      -0.0013261000
_diffrn_orient_matrix_UB_21      0.0389740000
_diffrn_orient_matrix_UB_22      -0.0009807000
_diffrn_orient_matrix_UB_23      0.0255105000
_diffrn_orient_matrix_UB_31      -0.0504532000
_diffrn_orient_matrix_UB_32      -0.0008646000
_diffrn_orient_matrix_UB_33      0.0196928000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus X-Ray tube'
_diffrn_source_type              'Agilent SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7473
_reflns_number_total             9622
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  
'encif (Wadepohl, 2009-17); encifer 1.5.2 (CCDC, 2016)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_shelxl_version_number           2016/6
_computing_structure_solution    'SUPERFLIP (Palatinus, 2007-2009)'
_refine_diff_density_max         1.009
_refine_diff_density_min         -0.696
_refine_diff_density_rms         0.102
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         9622
_refine_ls_number_restraints     144
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0371
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0343P)²+5.7256P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0798
_refine_ls_wR_factor_ref         0.0864
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 Sb-F1 \\sim Sb-F2 \\sim Sb-F3 \\sim Sb-F4 \\sim Sb-F5 \\sim Sb-F6
 with sigma of 0.01
 F1-F2 \\sim F1-F3 \\sim F1-F4 \\sim F1-F5 \\sim F6-F2 \\sim F6-F3 \\sim F6-F4
\\sim F6-F5 \\sim F2-F3 \\sim F2-F5
 \\sim F3-F4 \\sim F4-F5
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 F1, F2, F3, F4, F5, F6, Sb
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C52(H52), C53(H53), C54(H54), C55(H55), C56(H56)
4.b Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C10(H10A,
 H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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 0.750000 0.750000 0.29336(2) 0.02607(9) Uani 1 2 d S T P . .
Cu2 Cu 0.750000 0.750000 0.42636(2) 0.02275(9) Uani 1 2 d S T P . .
Cl Cl 0.59403(5) 0.77427(3) 0.35844(2) 0.03037(13) Uani 1 1 d . . . . .
N1 N 0.69220(16) 0.69968(8) 0.22064(7) 0.0179(3) Uani 1 1 d . . . . .
N2 N 0.49704(17) 0.65990(9) 0.21593(9) 0.0226(4) Uani 1 1 d . . . . .
N3 N 0.65813(19) 0.60153(9) 0.25029(9) 0.0242(4) Uani 1 1 d . . . . .
N4 N 0.70222(16) 0.80296(8) 0.50037(8) 0.0174(3) Uani 1 1 d . . . . .
N5 N 0.66314(17) 0.90001(8) 0.46790(8) 0.0207(4) Uani 1 1 d . . . . .
N6 N 0.50431(16) 0.84034(9) 0.50169(8) 0.0208(4) Uani 1 1 d . . . . .
C1 C 0.71290(17) 0.72197(9) 0.16541(9) 0.0146(4) Uani 1 1 d . . . . .
C2 C 0.67810(18) 0.69632(9) 0.11032(9) 0.0160(4) Uani 1 1 d . . . . .
H2 H 0.628583 0.661504 0.110182 0.019 Uiso 1 1 calc R . . . .
C3 C 0.71540(17) 0.72137(9) 0.05563(9) 0.0145(4) Uani 1 1 d . . . . .
C4 C 0.61410(19) 0.65238(9) 0.22787(9) 0.0173(4) Uani 1 1 d . . . . .
C5 C 0.4183(2) 0.61038(13) 0.19710(14) 0.0351(6) Uani 1 1 d . . . . .
H5A H 0.467120 0.574860 0.187738 0.053 Uiso 1 1 calc GR . . . .
H5B H 0.372949 0.622341 0.160859 0.053 Uiso 1 1 calc GR . . . .
H5C H 0.362305 0.600828 0.230115 0.053 Uiso 1 1 calc GR . . . .
C6 C 0.4474(2) 0.72032(12) 0.20748(12) 0.0292(5) Uani 1 1 d . . . . .
H6A H 0.491328 0.748873 0.233174 0.044 Uiso 1 1 calc GR . . . .
H6B H 0.362279 0.720385 0.218889 0.044 Uiso 1 1 calc GR . . . .
H6C H 0.455484 0.732150 0.164736 0.044 Uiso 1 1 calc GR . . . .
C7 C 0.5878(3) 0.55879(12) 0.28654(13) 0.0400(7) Uani 1 1 d . . . . .
H7A H 0.511379 0.577367 0.298291 0.060 Uiso 1 1 calc GR . . . .
H7B H 0.633037 0.547863 0.323159 0.060 Uiso 1 1 calc GR . . . .
H7C H 0.572032 0.522590 0.262392 0.060 Uiso 1 1 calc GR . . . .
C8 C 0.7876(2) 0.59068(12) 0.24838(13) 0.0352(6) Uani 1 1 d . . . . .
H8A H 0.821875 0.610182 0.212358 0.053 Uiso 1 1 calc GR . . . .
H8B H 0.802782 0.547293 0.246438 0.053 Uiso 1 1 calc GR . . . .
H8C H 0.825076 0.607275 0.285073 0.053 Uiso 1 1 calc GR . . . .
C9 C 0.62181(19) 0.84867(9) 0.49121(9) 0.0162(4) Uani 1 1 d . . . . .
C10 C 0.5937(2) 0.93663(12) 0.42528(13) 0.0340(6) Uani 1 1 d . . . . .
H10A H 0.524529 0.913484 0.410624 0.051 Uiso 1 1 calc GR . . . .
H10B H 0.644602 0.947903 0.390743 0.051 Uiso 1 1 calc GR . . . .
H10C H 0.565337 0.973044 0.445910 0.051 Uiso 1 1 calc GR . . . .
C11 C 0.7914(2) 0.91346(12) 0.47155(14) 0.0348(6) Uani 1 1 d . . . . .
H11A H 0.824858 0.895496 0.508576 0.052 Uiso 1 1 calc GR . . . .
H11B H 0.803056 0.957141 0.472638 0.052 Uiso 1 1 calc GR . . . .
H11C H 0.832409 0.896758 0.435895 0.052 Uiso 1 1 calc GR . . . .
C12 C 0.4220(2) 0.88935(13) 0.51530(13) 0.0330(6) Uani 1 1 d . . . . .
H12A H 0.468028 0.925197 0.526757 0.049 Uiso 1 1 calc GR . . . .
H12B H 0.369367 0.877664 0.549025 0.049 Uiso 1 1 calc GR . . . .
H12C H 0.373221 0.898224 0.479291 0.049 Uiso 1 1 calc GR . . . .
C13 C 0.4533(2) 0.77984(12) 0.50740(12) 0.0311(5) Uani 1 1 d . . . . .
H13A H 0.508069 0.750575 0.488848 0.047 Uiso 1 1 calc GR . . . .
H13B H 0.375441 0.778358 0.486648 0.047 Uiso 1 1 calc GR . . . .
H13C H 0.442419 0.770123 0.550527 0.047 Uiso 1 1 calc GR . . . .
N51 N 1.3564(2) 1.04274(10) 0.38826(11) 0.0361(5) Uani 1 1 d . . . . .
C52 C 1.1577(2) 0.92176(12) 0.40660(12) 0.0304(5) Uani 1 1 d . . . . .
H52 H 1.119917 0.949574 0.433262 0.037 Uiso 1 1 calc R . . . .
C53 C 1.1134(2) 0.86353(13) 0.40041(14) 0.0357(6) Uani 1 1 d . . . . .
H53 H 1.044780 0.851417 0.423029 0.043 Uiso 1 1 calc R . . . .
C54 C 1.1685(3) 0.82331(12) 0.36164(14) 0.0376(6) Uani 1 1 d . . . . .
H54 H 1.137547 0.783693 0.357605 0.045 Uiso 1 1 calc R . . . .
C55 C 1.2685(3) 0.84029(12) 0.32867(13) 0.0369(6) Uani 1 1 d . . . . .
H55 H 1.306212 0.812194 0.302302 0.044 Uiso 1 1 calc R . . . .
C56 C 1.3142(2) 0.89817(12) 0.33377(11) 0.0297(5) Uani 1 1 d . . . . .
H56 H 1.382605 0.909998 0.310813 0.036 Uiso 1 1 calc R . . . .
C57 C 1.2586(2) 0.93853(11) 0.37293(10) 0.0242(4) Uani 1 1 d . . . . .
C58 C 1.3101(2) 0.99729(11) 0.38112(11) 0.0278(5) Uani 1 1 d . . . . .
Sb Sb 0.07882(2) 0.89637(2) 0.61669(2) 0.01985(4) Uani 1 1 d D U . . .
F1 F 0.20837(15) 0.95003(8) 0.61837(10) 0.0521(5) Uani 1 1 d D U . . .
F2 F -0.02743(17) 0.95831(9) 0.63326(14) 0.0820(8) Uani 1 1 d D U . . .
F3 F 0.0599(3) 0.9119(2) 0.53539(11) 0.1497(18) Uani 1 1 d D U . . .
F4 F 0.18661(19) 0.83489(9) 0.60231(16) 0.1051(12) Uani 1 1 d D U . . .
F5 F 0.0969(2) 0.88329(17) 0.69869(11) 0.1124(12) Uani 1 1 d D U . . .
F6 F -0.04922(17) 0.84308(9) 0.61432(11) 0.0655(7) Uani 1 1 d D U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 Cu2 2.9240(5) . ?
Cu1 Cl 2.3128(6) . ?
Cu1 Cl 2.3127(6) 2_665 ?
Cu1 N1 2.0545(17) . ?
Cu1 N1 2.0545(17) 2_665 ?
Cu2 Cl 2.3519(6) . ?
Cu2 Cl 2.3519(6) 2_665 ?
Cu2 N4 2.0776(17) 2_665 ?
Cu2 N4 2.0776(17) . ?
N1 C1 1.332(2) . ?
N1 C4 1.373(3) . ?
N2 C4 1.339(3) . ?
N2 C5 1.466(3) . ?
N2 C6 1.464(3) . ?
N3 C4 1.327(3) . ?
N3 C7 1.466(3) . ?
N3 C8 1.461(3) . ?
N4 C3 1.338(2) 8_576 ?
N4 C9 1.369(3) . ?
N5 C9 1.333(3) . ?
N5 C10 1.462(3) . ?
N5 C11 1.460(3) . ?
N6 C9 1.340(3) . ?
N6 C12 1.454(3) . ?
N6 C13 1.465(3) . ?
C1 C1 1.495(4) 2_665 ?
C1 C2 1.393(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.389(3) . ?
C3 C3 1.488(4) 2_665 ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
N51 C58 1.145(3) . ?
C52 H52 0.9500 . ?
C52 C53 1.392(4) . ?
C52 C57 1.395(3) . ?
C53 H53 0.9500 . ?
C53 C54 1.379(4) . ?
C54 H54 0.9500 . ?
C54 C55 1.380(4) . ?
C55 H55 0.9500 . ?
C55 C56 1.388(4) . ?
C56 H56 0.9500 . ?
C56 C57 1.389(3) . ?
C57 C58 1.438(3) . ?
Sb F1 1.8713(16) . ?
Sb F2 1.8511(18) . ?
Sb F3 1.833(2) . ?
Sb F4 1.8455(19) . ?
Sb F5 1.837(2) . ?
Sb F6 1.8534(17) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl Cu1 Cu2 51.784(15) 2_665 . ?
Cl Cu1 Cu2 51.783(15) . . ?
Cl Cu1 Cl 103.57(3) 2_665 . ?
N1 Cu1 Cu2 141.09(5) 2_665 . ?
N1 Cu1 Cu2 141.09(5) . . ?
N1 Cu1 Cl 126.10(5) . 2_665 ?
N1 Cu1 Cl 126.10(5) 2_665 . ?
N1 Cu1 Cl 111.94(5) 2_665 2_665 ?
N1 Cu1 Cl 111.94(5) . . ?
N1 Cu1 N1 77.81(9) . 2_665 ?
Cl Cu2 Cu1 50.587(15) 2_665 . ?
Cl Cu2 Cu1 50.589(15) . . ?
Cl Cu2 Cl 101.18(3) . 2_665 ?
N4 Cu2 Cu1 141.56(5) . . ?
N4 Cu2 Cu1 141.55(5) 2_665 . ?
N4 Cu2 Cl 144.69(5) 2_665 . ?
N4 Cu2 Cl 100.28(5) 2_665 2_665 ?
N4 Cu2 Cl 144.69(5) . 2_665 ?
N4 Cu2 Cl 100.28(5) . . ?
N4 Cu2 N4 76.89(9) 2_665 . ?
Cu1 Cl Cu2 77.63(2) . . ?
C1 N1 Cu1 116.93(14) . . ?
C1 N1 C4 119.99(17) . . ?
C4 N1 Cu1 121.66(13) . . ?
C4 N2 C5 122.9(2) . . ?
C4 N2 C6 120.40(19) . . ?
C6 N2 C5 115.3(2) . . ?
C4 N3 C7 123.8(2) . . ?
C4 N3 C8 119.6(2) . . ?
C8 N3 C7 115.8(2) . . ?
C3 N4 Cu2 117.01(13) 8_576 . ?
C3 N4 C9 120.35(17) 8_576 . ?
C9 N4 Cu2 118.21(13) . . ?
C9 N5 C10 122.7(2) . . ?
C9 N5 C11 119.42(19) . . ?
C11 N5 C10 116.0(2) . . ?
C9 N6 C12 123.1(2) . . ?
C9 N6 C13 121.28(19) . . ?
C12 N6 C13 115.2(2) . . ?
N1 C1 C1 113.93(11) . 2_665 ?
N1 C1 C2 126.32(18) . . ?
C2 C1 C1 119.64(11) . 2_665 ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.36(18) . . ?
C3 C2 H2 119.8 . . ?
N4 C3 C2 126.26(18) 8_575 . ?
N4 C3 C3 113.75(11) 8_575 2_665 ?
C2 C3 C3 119.85(11) . 2_665 ?
N2 C4 N1 119.81(19) . . ?
N3 C4 N1 117.49(19) . . ?
N3 C4 N2 122.56(19) . . ?
N2 C5 H5A 109.5 . . ?
N2 C5 H5B 109.5 . . ?
N2 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N2 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
N2 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N3 C7 H7A 109.5 . . ?
N3 C7 H7B 109.5 . . ?
N3 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N3 C8 H8A 109.5 . . ?
N3 C8 H8B 109.5 . . ?
N3 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N5 C9 N4 117.83(19) . . ?
N5 C9 N6 121.39(19) . . ?
N6 C9 N4 120.63(19) . . ?
N5 C10 H10A 109.5 . . ?
N5 C10 H10B 109.5 . . ?
N5 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N5 C11 H11A 109.5 . . ?
N5 C11 H11B 109.5 . . ?
N5 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N6 C12 H12A 109.5 . . ?
N6 C12 H12B 109.5 . . ?
N6 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N6 C13 H13A 109.5 . . ?
N6 C13 H13B 109.5 . . ?
N6 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C53 C52 H52 120.6 . . ?
C53 C52 C57 118.8(2) . . ?
C57 C52 H52 120.6 . . ?
C52 C53 H53 119.8 . . ?
C54 C53 C52 120.4(3) . . ?
C54 C53 H53 119.8 . . ?
C53 C54 H54 119.8 . . ?
C53 C54 C55 120.4(3) . . ?
C55 C54 H54 119.8 . . ?
C54 C55 H55 119.8 . . ?
C54 C55 C56 120.4(3) . . ?
C56 C55 H55 119.8 . . ?
C55 C56 H56 120.5 . . ?
C55 C56 C57 119.0(2) . . ?
C57 C56 H56 120.5 . . ?
C52 C57 C58 119.8(2) . . ?
C56 C57 C52 121.0(2) . . ?
C56 C57 C58 119.1(2) . . ?
N51 C58 C57 176.6(3) . . ?
F2 Sb F1 90.79(9) . . ?
F2 Sb F6 89.44(9) . . ?
F3 Sb F1 89.28(12) . . ?
F3 Sb F2 88.73(17) . . ?
F3 Sb F4 92.73(18) . . ?
F3 Sb F5 178.18(19) . . ?
F3 Sb F6 90.28(13) . . ?
F4 Sb F1 88.56(9) . . ?
F4 Sb F2 178.39(14) . . ?
F4 Sb F6 91.22(9) . . ?
F5 Sb F1 89.83(12) . . ?
F5 Sb F2 89.69(15) . . ?
F5 Sb F4 88.83(16) . . ?
F5 Sb F6 90.62(12) . . ?
F6 Sb F1 179.50(10) . . ?

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
Cu1 N1 C1 C1 5.9(3) . . . 2_665 ?
Cu1 N1 C1 C2 -177.83(16) . . . . ?
Cu1 N1 C4 N2 100.0(2) . . . . ?
Cu1 N1 C4 N3 -76.0(2) . . . . ?
Cu2 N4 C9 N5 -80.8(2) . . . . ?
Cu2 N4 C9 N6 94.9(2) . . . . ?
N1 C1 C2 C3 -173.9(2) . . . . ?
C1 N1 C4 N2 -66.0(3) . . . . ?
C1 N1 C4 N3 118.0(2) . . . . ?
C1 C1 C2 C3 2.2(3) 2_665 . . . ?
C1 C2 C3 N4 170.5(2) . . . 8_575 ?
C1 C2 C3 C3 -4.9(3) . . . 2_665 ?
C3 N4 C9 N5 123.5(2) 8_576 . . . ?
C3 N4 C9 N6 -60.8(3) 8_576 . . . ?
C4 N1 C1 C1 172.6(2) . . . 2_665 ?
C4 N1 C1 C2 -11.2(3) . . . . ?
C5 N2 C4 N1 153.2(2) . . . . ?
C5 N2 C4 N3 -31.1(3) . . . . ?
C6 N2 C4 N1 -12.6(3) . . . . ?
C6 N2 C4 N3 163.1(2) . . . . ?
C7 N3 C4 N1 150.2(2) . . . . ?
C7 N3 C4 N2 -25.6(3) . . . . ?
C8 N3 C4 N1 -19.1(3) . . . . ?
C8 N3 C4 N2 165.0(2) . . . . ?
C10 N5 C9 N4 143.8(2) . . . . ?
C10 N5 C9 N6 -31.8(3) . . . . ?
C11 N5 C9 N4 -19.9(3) . . . . ?
C11 N5 C9 N6 164.4(2) . . . . ?
C12 N6 C9 N4 156.1(2) . . . . ?
C12 N6 C9 N5 -28.3(3) . . . . ?
C13 N6 C9 N4 -16.3(3) . . . . ?
C13 N6 C9 N5 159.2(2) . . . . ?
C52 C53 C54 C55 0.2(4) . . . . ?
C53 C52 C57 C56 0.1(4) . . . . ?
C53 C52 C57 C58 -176.5(2) . . . . ?
C53 C54 C55 C56 -0.5(4) . . . . ?
C54 C55 C56 C57 0.6(4) . . . . ?
C55 C56 C57 C52 -0.4(4) . . . . ?
C55 C56 C57 C58 176.2(2) . . . . ?
C57 C52 C53 C54 0.0(4) . . . . ?
_audit_block_usercomment         'hi_az327a, plate, dark yellow'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.189
_oxdiff_exptl_absorpt_empirical_full_min 0.864
_cell_oxdiff_length_a            11.12566(16)
_cell_oxdiff_length_b            22.2244(5)
_cell_oxdiff_length_c            21.9908(3)
_cell_oxdiff_angle_alpha         90.0135(14)
_cell_oxdiff_angle_beta          90.0118(12)
_cell_oxdiff_angle_gamma         89.9772(14)
_cell_oxdiff_volume              5437.48(16)
_cell_oxdiff_measurement_reflns_used 33535
_symmetry_cell_setting           orthorhombic
#_space_group_name_H-M_alt       'P c c n'
#_space_group_IT_number          56
_chemical_absolute_configuration .
_diffrn_measurement_specimen_support 'polyimid foil'
####################################################################### 
# 
# 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_hi_az16
_database_code_depnum_ccdc_archive 'CCDC 1563141'
_audit_update_record             
;
2017-07-19 deposited with the CCDC.
2018-06-21 downloaded from the CCDC.
;
#==============================================================================
_audit_creation_date             2016-09-21

_audit_block_code                hi_az16
_audit_block_refno               2765
_audit_block_usercomment         'hi_az307a, block, black'

# start Validation Reply Form
_vrf_PLAT971_hi_az16             
;
PROBLEM: Check Calcd Residual Density  0.56A From     Sb1       3.05 eA-3  
RESPONSE: residual absorption effects and/or unresolved disorder
          around special position
;
# end Validation Reply Form

_audit_creation_method           
;
Olex2 1.2
(compiled Sep  9 2016 16:03:45 for OlexSys, GUI svn.r5227)
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C30 H56 Cl2 Cu2 N14, 2(F6 Sb)'
_chemical_formula_sum            'C30 H56 Cl2 Cu2 F12 N14 Sb2'
_chemical_properties_physical    'air-sensitive, moisture-sensitive'
_chemical_formula_weight         1282.36
_chemical_melting_point          ?
_exptl_crystal_description       block
_exptl_crystal_colour            black
_diffrn_ambient_temperature      120(1)
_chemical_oxdiff_formula         'C30 H56 F12 N14 Cu2 Cl2 Sb2'
_chemical_oxdiff_usercomment     'hi_az307a, block, black'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P bc n '
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_h-m   'P b c n'
_symmetry_int_tables_number      60
_chemical_absolute_configuration .

_space_group_name_Hall           '-P 2n 2ab'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'

_cell_length_a                   16.08984(16)
_cell_length_b                   18.88601(13)
_cell_length_c                   15.90472(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4833.01(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    47362
_cell_measurement_temperature    120(1)
_cell_measurement_theta_max      31.3700
_cell_measurement_theta_min      3.5440
_shelx_estimated_absorpt_T_max   0.812
_shelx_estimated_absorpt_T_min   0.812
_exptl_absorpt_coefficient_mu    2.171
_exptl_absorpt_correction_T_max  0.872
_exptl_absorpt_correction_T_min  0.760
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.762
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             2544
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
16 -2 16 0.0655
3 -20 -15 0.0498
14 1 -17 0.0687
-14 -1 17 0.0687
5 -18 15 0.0473
-17 2 -15 0.0575
-17 -18 2 0.0624
-5 -19 -15 0.0425
11 -16 14 0.0459
0 27 0 0.0333
-12 -17 -13 0.0424
-1 -18 16 0.0502
_exptl_crystal_size_max          0.152
_exptl_crystal_size_mid          0.127
_exptl_crystal_size_min          0.097
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
15.9947 -2.0017 15.9945 -0.0454 0.4239 -0.9110
3.0007 -19.9916 -14.9969 -0.8160 0.2831 0.5318
13.9965 1.0033 -16.9947 -0.0657 0.8322 0.5089
-13.9965 -1.0033 16.9947 0.0657 -0.8322 -0.5089
4.9988 -17.9975 14.9937 -0.6214 -0.0662 -0.7493
-16.9945 2.0015 -14.9949 0.0519 -0.4800 0.8839
-16.9942 -17.9959 1.9981 -0.6243 -0.7890 0.1191
-4.9970 -18.9921 -14.9968 -0.7601 -0.0458 0.6522
10.9970 -15.9976 13.9941 -0.5648 0.2033 -0.7904
-0.0013 26.9924 0.0022 1.0081 0.0817 0.0709
-12.0000 -17.0000 -13.0000 -0.6611 -0.3595 0.6768
-1.0000 -17.9999 16.0000 -0.6034 -0.3299 -0.7032

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0497
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            174732
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.421
_diffrn_reflns_theta_min         3.036
_diffrn_ambient_environment      perfluoro
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 7.9621
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -42.00  48.00   0.50   12.50    --   27.02 -57.00 -30.00  180
  2  ω     -3.00  97.00   0.50   12.50    --   27.02  77.00 -90.00  200
  3  ω      7.00  96.00   0.50   12.50    --   27.02  57.00-150.00  178
  4  ω      7.00  96.00   0.50   12.50    --   27.02  57.00  30.00  178
  5  ω     12.00  96.00   0.50   12.50    --   27.02-144.00 -22.00  168
  6  ω    -43.00  57.00   0.50   12.50    --   27.02 -77.00 150.00  200
  7  ω    -42.00  48.00   0.50   12.50    --   27.02 -57.00-120.00  180
  8  ω    -20.00  69.00   0.50   12.50    --   27.02 -99.00  60.00  178
  9  ω     -3.00  97.00   0.50   12.50    --   27.02  77.00  90.00  200
 10  ω      2.00  99.00   0.50   12.50    --   27.02  38.00  30.00  194
 11  ω     -3.00  97.00   0.50   12.50    --   27.02  77.00 120.00  200
 12  ω     -3.00  97.00   0.50   12.50    --   27.02  77.00   0.00  200
 13  ω    -20.00  69.00   0.50   12.50    --   27.02 -99.00-150.00  178
 14  ω     -3.00  97.00   0.50   12.50    --   27.02  77.00-180.00  200
 15  ω      2.00  81.00   0.50   12.50    --   27.02  38.00-150.00  158
 16  ω    -42.00  48.00   0.50   12.50    --   27.02 -57.00  60.00  180
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Agilent SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0023225000
_diffrn_orient_matrix_UB_12      0.0373479000
_diffrn_orient_matrix_UB_13      0.0041584000
_diffrn_orient_matrix_UB_21      0.0414985000
_diffrn_orient_matrix_UB_22      0.0030313000
_diffrn_orient_matrix_UB_23      -0.0146146000
_diffrn_orient_matrix_UB_31      -0.0147184000
_diffrn_orient_matrix_UB_32      0.0026282000
_diffrn_orient_matrix_UB_33      -0.0419118000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus X-Ray tube'
_diffrn_source_type              'Agilent SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7213
_reflns_number_total             8562
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  
'encif (Wadepohl, 2009-15); encifer 1.5 (CCDC, 2014)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_shelxl_version_number           2014/7
_computing_structure_solution    'SUPERFLIP (Palatinus, 2007-2009)'
_refine_diff_density_max         3.079
_refine_diff_density_min         -2.506
_refine_diff_density_rms         0.114
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         8562
_refine_ls_number_restraints     154
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0454
_refine_ls_restrained_S_all      1.116
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0366P)²+14.5636P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1026
_refine_ls_wR_factor_ref         0.1077
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 Sb1-F11 \\sim Sb1-F12 \\sim Sb1-F13 \\sim Sb1-F14 \\sim Sb2-F21 \\sim Sb2-F22
\\sim Sb2-F23 \\sim Sb2-F24
 with sigma of 0.02
 F11-F12 \\sim F11-F13 \\sim F14-F12 \\sim F14-F13 \\sim F12-F13 \\sim
F12-F13_$1 \\sim F21-F22 \\sim F21-
 F23 \\sim F24-F22 \\sim F24-F23 \\sim F22-F23 \\sim F22-F23_$2
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 Sb2, Sb1, F11, F13, F14, F21, F12, F22, F23, F24
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4.a Aromatic/amide H refined with riding coordinates:
 C3(H3)
4.b Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C10(H10A,
 H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C),
 C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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
Cu Cu 0.32041(2) 0.22443(2) 0.42107(2) 0.01753(7) Uani 1 1 d . . . . .
Cl Cl 0.24426(4) 0.30481(3) 0.49433(4) 0.02195(11) Uani 1 1 d . . . . .
N1 N 0.33526(12) 0.24870(11) 0.29513(12) 0.0157(3) Uani 1 1 d . . . . .
N2 N 0.25397(14) 0.32964(13) 0.22167(13) 0.0242(4) Uani 1 1 d . . . . .
N3 N 0.22503(14) 0.20917(14) 0.21239(14) 0.0275(5) Uani 1 1 d . . . . .
N4 N 0.44635(12) 0.24797(11) 0.41400(11) 0.0149(3) Uani 1 1 d . . . . .
N5 N 0.51650(13) 0.32707(13) 0.50116(14) 0.0223(4) Uani 1 1 d . . . . .
N6 N 0.52405(14) 0.20588(13) 0.52733(14) 0.0240(4) Uani 1 1 d . . . . .
N7 N 0.29919(14) 0.12419(12) 0.43980(13) 0.0216(4) Uani 1 1 d . . . . .
C1 C 0.41334(13) 0.25372(11) 0.26830(13) 0.0133(4) Uani 1 1 d . . . . .
C2 C 0.47724(13) 0.25346(11) 0.33665(13) 0.0134(4) Uani 1 1 d . . . . .
C9 C 0.49844(14) 0.25989(13) 0.48103(14) 0.0165(4) Uani 1 1 d . . . . .
C3 C 0.56144(13) 0.25640(12) 0.31575(13) 0.0142(4) Uani 1 1 d . . . . .
H3 H 0.6019 0.2603 0.3590 0.017 Uiso 1 1 calc R . . . .
C4 C 0.27123(14) 0.26201(14) 0.23983(14) 0.0180(4) Uani 1 1 d . . . . .
C5 C 0.2220(2) 0.35239(19) 0.13965(18) 0.0382(7) Uani 1 1 d . . . . .
H5A H 0.2223 0.3122 0.1007 0.057 Uiso 1 1 calc GR . . . .
H5B H 0.2574 0.3902 0.1173 0.057 Uiso 1 1 calc GR . . . .
H5C H 0.1651 0.3700 0.1461 0.057 Uiso 1 1 calc GR . . . .
C6 C 0.2890(2) 0.38668(16) 0.27297(19) 0.0340(6) Uani 1 1 d . . . . .
H6A H 0.2929 0.3710 0.3316 0.051 Uiso 1 1 calc GR . . . .
H6B H 0.2530 0.4284 0.2696 0.051 Uiso 1 1 calc GR . . . .
H6C H 0.3445 0.3987 0.2521 0.051 Uiso 1 1 calc GR . . . .
C7 C 0.13953(19) 0.2192(3) 0.1832(2) 0.0475(10) Uani 1 1 d . . . . .
H7A H 0.1174 0.2635 0.2062 0.071 Uiso 1 1 calc GR . . . .
H7B H 0.1051 0.1795 0.2021 0.071 Uiso 1 1 calc GR . . . .
H7C H 0.1388 0.2214 0.1216 0.071 Uiso 1 1 calc GR . . . .
C8 C 0.2549(2) 0.13636(18) 0.2146(2) 0.0407(8) Uani 1 1 d . . . . .
H8A H 0.3138 0.1359 0.2304 0.061 Uiso 1 1 calc GR . . . .
H8B H 0.2482 0.1148 0.1590 0.061 Uiso 1 1 calc GR . . . .
H8C H 0.2229 0.1094 0.2561 0.061 Uiso 1 1 calc GR . . . .
C10 C 0.59773(18) 0.34831(18) 0.5348(2) 0.0366(7) Uani 1 1 d . . . . .
H10A H 0.5911 0.3647 0.5929 0.055 Uiso 1 1 calc GR . . . .
H10B H 0.6206 0.3867 0.5004 0.055 Uiso 1 1 calc GR . . . .
H10C H 0.6357 0.3077 0.5335 0.055 Uiso 1 1 calc GR . . . .
C11 C 0.46667(18) 0.38508(15) 0.4668(2) 0.0299(6) Uani 1 1 d . . . . .
H11A H 0.4881 0.3982 0.4113 0.045 Uiso 1 1 calc GR . . . .
H11B H 0.4698 0.4260 0.5045 0.045 Uiso 1 1 calc GR . . . .
H11C H 0.4087 0.3698 0.4616 0.045 Uiso 1 1 calc GR . . . .
C12 C 0.55241(19) 0.2133(2) 0.61459(17) 0.0390(8) Uani 1 1 d . . . . .
H12A H 0.6133 0.2123 0.6162 0.058 Uiso 1 1 calc GR . . . .
H12B H 0.5304 0.1741 0.6483 0.058 Uiso 1 1 calc GR . . . .
H12C H 0.5325 0.2583 0.6376 0.058 Uiso 1 1 calc GR . . . .
C13 C 0.5227(2) 0.13380(16) 0.4940(2) 0.0361(7) Uani 1 1 d . . . . .
H13A H 0.4860 0.1044 0.5286 0.054 Uiso 1 1 calc GR . . . .
H13B H 0.5791 0.1141 0.4950 0.054 Uiso 1 1 calc GR . . . .
H13C H 0.5022 0.1345 0.4360 0.054 Uiso 1 1 calc GR . . . .
C14 C 0.28939(19) 0.06564(15) 0.45065(18) 0.0286(5) Uani 1 1 d . . . . .
C15 C 0.2751(3) -0.00969(19) 0.4664(3) 0.0624(13) Uani 1 1 d . . . . .
H15A H 0.3042 -0.0378 0.4237 0.094 Uiso 1 1 calc GR . . . .
H15B H 0.2154 -0.0197 0.4637 0.094 Uiso 1 1 calc GR . . . .
H15C H 0.2963 -0.0221 0.5223 0.094 Uiso 1 1 calc GR . . . .
Sb2 Sb 0.5000 0.48310(2) 0.7500 0.03762(9) Uani 1 2 d DS TU P . .
Sb1 Sb 0.0000 0.49946(2) 0.7500 0.04601(10) Uani 1 2 d DS TU P . .
F11 F 0.0000 0.4043(2) 0.7500 0.142(3) Uani 1 2 d DS TU P . .
F13 F -0.0918(3) 0.5023(4) 0.6840(4) 0.197(3) Uani 1 1 d D U . . .
F14 F 0.0000 0.5964(2) 0.7500 0.223(5) Uani 1 2 d DS TU P . .
F21 F 0.5000 0.38421(16) 0.7500 0.0830(15) Uani 1 2 d DS TU P . .
F12 F 0.0628(3) 0.4998(3) 0.6522(3) 0.1451(19) Uani 1 1 d D U . . .
F22 F 0.58960(15) 0.48258(13) 0.67448(17) 0.0598(7) Uani 1 1 d D U . . .
F23 F 0.57449(16) 0.48259(13) 0.84033(16) 0.0560(6) Uani 1 1 d D U . . .
F24 F 0.5000 0.58161(13) 0.7500 0.0371(6) Uani 1 2 d DS TU 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
Cu Cl 2.2724(7) . ?
Cu N1 2.0687(19) . ?
Cu N4 2.0777(19) . ?
Cu N7 1.947(2) . ?
N1 C1 1.330(3) . ?
N1 C4 1.378(3) . ?
N2 C4 1.339(3) . ?
N2 C5 1.466(3) . ?
N2 C6 1.464(4) . ?
N3 C4 1.319(3) . ?
N3 C7 1.464(4) . ?
N3 C8 1.457(4) . ?
N4 C2 1.331(3) . ?
N4 C9 1.375(3) . ?
N5 C9 1.340(3) . ?
N5 C10 1.468(3) . ?
N5 C11 1.464(4) . ?
N6 C9 1.324(3) . ?
N6 C12 1.468(4) . ?
N6 C13 1.461(4) . ?
N7 C14 1.130(4) . ?
C1 C2 1.496(3) . ?
C1 C3 1.398(3) 4_655 ?
C2 C3 1.396(3) . ?
C3 C1 1.398(3) 4_655 ?
C3 H3 0.9500 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.463(4) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
Sb2 F21 1.868(3) . ?
Sb2 F22 1.876(3) . ?
Sb2 F22 1.877(3) 4_656 ?
Sb2 F23 1.871(2) 4_656 ?
Sb2 F23 1.871(2) . ?
Sb2 F24 1.860(2) . ?
Sb1 F11 1.796(4) . ?
Sb1 F13 1.813(4) 4_556 ?
Sb1 F13 1.813(4) . ?
Sb1 F14 1.830(4) . ?
Sb1 F12 1.855(4) . ?
Sb1 F12 1.855(4) 4_556 ?

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 Cu Cl 114.25(6) . . ?
N1 Cu N4 77.73(7) . . ?
N4 Cu Cl 114.25(6) . . ?
N7 Cu Cl 118.47(7) . . ?
N7 Cu N1 112.58(8) . . ?
N7 Cu N4 112.80(9) . . ?
C1 N1 Cu 115.82(15) . . ?
C1 N1 C4 119.24(19) . . ?
C4 N1 Cu 124.91(15) . . ?
C4 N2 C5 123.0(2) . . ?
C4 N2 C6 120.1(2) . . ?
C6 N2 C5 114.5(3) . . ?
C4 N3 C7 122.4(3) . . ?
C4 N3 C8 121.3(2) . . ?
C8 N3 C7 116.1(3) . . ?
C2 N4 Cu 115.52(15) . . ?
C2 N4 C9 118.46(19) . . ?
C9 N4 Cu 126.00(15) . . ?
C9 N5 C10 122.6(2) . . ?
C9 N5 C11 120.0(2) . . ?
C11 N5 C10 114.8(2) . . ?
C9 N6 C12 123.3(3) . . ?
C9 N6 C13 120.8(2) . . ?
C13 N6 C12 115.9(3) . . ?
C14 N7 Cu 177.9(2) . . ?
N1 C1 C2 114.56(18) . . ?
N1 C1 C3 125.7(2) . 4_655 ?
C3 C1 C2 119.70(19) 4_655 . ?
N4 C2 C1 114.54(19) . . ?
N4 C2 C3 125.8(2) . . ?
C3 C2 C1 119.58(18) . . ?
N5 C9 N4 118.2(2) . . ?
N6 C9 N4 119.7(2) . . ?
N6 C9 N5 121.9(2) . . ?
C1 C3 H3 119.7 4_655 . ?
C2 C3 C1 120.53(19) . 4_655 ?
C2 C3 H3 119.7 . . ?
N2 C4 N1 117.8(2) . . ?
N3 C4 N1 119.7(2) . . ?
N3 C4 N2 122.3(2) . . ?
N2 C5 H5A 109.5 . . ?
N2 C5 H5B 109.5 . . ?
N2 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N2 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
N2 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N3 C7 H7A 109.5 . . ?
N3 C7 H7B 109.5 . . ?
N3 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N3 C8 H8A 109.5 . . ?
N3 C8 H8B 109.5 . . ?
N3 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N5 C10 H10A 109.5 . . ?
N5 C10 H10B 109.5 . . ?
N5 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N5 C11 H11A 109.5 . . ?
N5 C11 H11B 109.5 . . ?
N5 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N6 C12 H12A 109.5 . . ?
N6 C12 H12B 109.5 . . ?
N6 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N6 C13 H13A 109.5 . . ?
N6 C13 H13B 109.5 . . ?
N6 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N7 C14 C15 178.5(4) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
F21 Sb2 F22 89.70(8) . 4_656 ?
F21 Sb2 F22 89.70(8) . . ?
F21 Sb2 F23 89.71(7) . 4_656 ?
F21 Sb2 F23 89.71(7) . . ?
F22 Sb2 F22 179.40(16) . 4_656 ?
F23 Sb2 F22 90.03(12) 4_656 . ?
F23 Sb2 F22 90.03(12) . 4_656 ?
F23 Sb2 F22 89.96(12) . . ?
F23 Sb2 F22 89.96(12) 4_656 4_656 ?
F23 Sb2 F23 179.41(15) 4_656 . ?
F24 Sb2 F21 180.0 . . ?
F24 Sb2 F22 90.30(8) . 4_656 ?
F24 Sb2 F22 90.30(8) . . ?
F24 Sb2 F23 90.29(7) . . ?
F24 Sb2 F23 90.29(7) . 4_656 ?
F11 Sb1 F13 91.7(2) . . ?
F11 Sb1 F13 91.7(2) . 4_556 ?
F11 Sb1 F14 180.0 . . ?
F11 Sb1 F12 90.23(15) . . ?
F11 Sb1 F12 90.23(15) . 4_556 ?
F13 Sb1 F13 176.6(4) 4_556 . ?
F13 Sb1 F14 88.3(2) . . ?
F13 Sb1 F14 88.3(2) 4_556 . ?
F13 Sb1 F12 92.4(2) . 4_556 ?
F13 Sb1 F12 87.6(2) . . ?
F13 Sb1 F12 87.6(2) 4_556 4_556 ?
F13 Sb1 F12 92.4(2) 4_556 . ?
F14 Sb1 F12 89.77(15) . 4_556 ?
F14 Sb1 F12 89.77(15) . . ?
F12 Sb1 F12 179.5(3) 4_556 . ?

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
Cu N1 C1 C2 -10.2(2) . . . . ?
Cu N1 C1 C3 167.37(18) . . . 4_655 ?
Cu N1 C4 N2 100.3(2) . . . . ?
Cu N1 C4 N3 -74.1(3) . . . . ?
Cu N4 C2 C1 9.7(2) . . . . ?
Cu N4 C2 C3 -168.02(18) . . . . ?
Cu N4 C9 N5 -100.0(2) . . . . ?
Cu N4 C9 N6 75.0(3) . . . . ?
N1 C1 C2 N4 0.2(3) . . . . ?
N1 C1 C2 C3 178.1(2) . . . . ?
N4 C2 C3 C1 172.4(2) . . . 4_655 ?
C1 N1 C4 N2 -77.3(3) . . . . ?
C1 N1 C4 N3 108.3(3) . . . . ?
C1 C2 C3 C1 -5.3(3) . . . 4_655 ?
C2 N4 C9 N5 78.2(3) . . . . ?
C2 N4 C9 N6 -106.9(3) . . . . ?
C9 N4 C2 C1 -168.6(2) . . . . ?
C9 N4 C2 C3 13.7(3) . . . . ?
C3 C1 C2 N4 -177.5(2) 4_655 . . . ?
C3 C1 C2 C3 0.4(3) 4_655 . . . ?
C4 N1 C1 C2 167.6(2) . . . . ?
C4 N1 C1 C3 -14.8(3) . . . 4_655 ?
C5 N2 C4 N1 148.0(3) . . . . ?
C5 N2 C4 N3 -37.8(4) . . . . ?
C6 N2 C4 N1 -13.5(4) . . . . ?
C6 N2 C4 N3 160.7(3) . . . . ?
C7 N3 C4 N1 154.7(2) . . . . ?
C7 N3 C4 N2 -19.3(4) . . . . ?
C8 N3 C4 N1 -21.3(4) . . . . ?
C8 N3 C4 N2 164.7(3) . . . . ?
C10 N5 C9 N4 -146.0(3) . . . . ?
C10 N5 C9 N6 39.2(4) . . . . ?
C11 N5 C9 N4 14.8(3) . . . . ?
C11 N5 C9 N6 -160.0(2) . . . . ?
C12 N6 C9 N4 -156.7(2) . . . . ?
C12 N6 C9 N5 18.1(4) . . . . ?
C13 N6 C9 N4 21.2(4) . . . . ?
C13 N6 C9 N5 -164.1(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.129
_oxdiff_exptl_absorpt_empirical_full_min 0.915
_cell_oxdiff_length_a            16.08665(16)
_cell_oxdiff_length_b            18.8831(2)
_cell_oxdiff_length_c            15.9103(2)
_cell_oxdiff_angle_alpha         90.0294(11)
_cell_oxdiff_angle_beta          90.0212(11)
_cell_oxdiff_angle_gamma         90.0129(10)
_cell_oxdiff_volume              4833.01(11)
_cell_oxdiff_measurement_reflns_used 47362
_diffrn_measurement_specimen_support 'polyimid foil'
####################################################################### 
# 
# 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_hi_az20
_database_code_depnum_ccdc_archive 'CCDC 1563143'
_audit_update_record             
;
2017-07-19 deposited with the CCDC.
2018-06-21 downloaded from the CCDC.
;
_audit_creation_date             2017-03-16

_audit_block_code                hi_az20
_audit_block_refno               2841
_audit_block_usercomment         'hi_az336, block, blue'


_audit_creation_method           
;
Olex2 1.2
(compiled Mar 28 2017 19:34:44 for OlexSys, GUI svn.r5337)
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C18 H24 Cu N6, C6 H8 N2, H2 O, 2(Cl)'
_chemical_formula_sum            'C24 H34 Cl2 Cu N8 O'
_chemical_formula_weight         585.03
_chemical_melting_point          ?
_exptl_crystal_description       block
_exptl_crystal_colour            'light blue'
_diffrn_ambient_temperature      120(1)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.6115(4)
_cell_length_b                   11.2052(4)
_cell_length_c                   12.3212(6)
_cell_angle_alpha                69.734(4)
_cell_angle_beta                 89.956(3)
_cell_angle_gamma                82.315(3)
_cell_volume                     1360.36(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    13466
_cell_measurement_temperature    120(1)
_cell_measurement_theta_max      70.5170
_cell_measurement_theta_min      4.2170
_exptl_absorpt_coefficient_mu    3.208
_exptl_absorpt_correction_T_max  0.79302
_exptl_absorpt_correction_T_min  0.78356
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Spherical absorption correction
 using equivalent radius and absorption coefficient.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             610
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
7 1 -1 0.0185
-7 -1 1 0.0314
0 -5 -7 0.0174
0 5 7 0.0174
0 6 -3 0.0177
0 -6 3 0.0177
_exptl_crystal_size_max          0.057
_exptl_crystal_size_mid          0.035
_exptl_crystal_size_min          0.035
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
6.9998 1.0001 -0.9999 -0.1727 0.8612 -0.5286
-6.9998 -1.0001 0.9999 0.1727 -0.8612 0.5286
0.0001 -4.9996 -6.9997 0.1212 -0.4056 -0.8707
-0.0001 4.9996 6.9997 -0.1212 0.4056 0.8707
-0.0005 5.9996 -3.0005 -1.0898 -0.1013 0.0072
0.0005 -5.9996 3.0005 1.0898 0.1013 -0.0072

_exptl_transmission_factor_max   1.304
_exptl_transmission_factor_min   0.827
_diffrn_reflns_av_R_equivalents  0.0502
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            42653
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.646
_diffrn_reflns_theta_min         3.829
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 7.9621
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -21.00  69.00   1.00    2.00    --    0.00  57.00  90.00   90
  2  ω    -26.00  72.00   1.00    2.00    --    0.00  38.00 -90.00   98
  3  ω    -26.00  72.00   1.00    2.00    --    0.00  38.00-150.00   98
  4  ω     36.00  85.00   1.00   16.00    --  108.00 -92.00-120.00   49
  5  ω    -35.00  10.00   1.00    2.00    --   14.00 111.00-145.76   45
  6  ω    -38.00 -11.00   1.00    8.00    --   30.00 142.00  -7.43   27
  7  ω     -9.00  18.00   1.00    8.00    --   34.00 102.00-142.50   27
  8  ω      5.00  32.00   1.00    8.00    --   42.00  90.00 -96.55   27
  9  ω     12.00  38.00   1.00    8.00    --   46.00  84.00-125.19   26
 10  ω     13.00  45.00   1.00    8.00    --   46.00  82.00 156.48   32
 11  ω     13.00  40.00   1.00    8.00    --   46.00  83.00 -28.63   27
 12  ω     12.00  38.00   1.00    8.00    --   46.00  84.00 115.66   26
 13  ω     12.00  38.00   1.00    8.00    --   46.00  84.00  48.46   26
 14  ω     26.00 123.00   1.00    8.00    --   54.00  73.00  20.50   97
 15  ω     24.00 124.00   1.00    8.00    --   54.00  77.00  90.00  100
 16  ω     24.00 124.00   1.00    8.00    --   54.00  77.00 120.00  100
 17  ω     24.00 124.00   1.00    8.00    --   54.00  77.00-180.00  100
 18  ω      1.00  96.00   1.00    8.00    --   54.00 -99.00   0.00   95
 19  ω     24.00 124.00   1.00    8.00    --   54.00  77.00  30.00  100
 20  ω     24.00 124.00   1.00    8.00    --   54.00  77.00 -90.00  100
 21  ω     24.00 124.00   1.00    8.00    --   54.00  77.00  60.00  100
 22  ω     33.00 123.00   1.00    8.00    --   54.00  57.00-120.00   90
 23  ω    -15.00  75.00   1.00    8.00    --   54.00 -57.00  30.00   90
 24  ω     25.00 124.00   1.00    8.00    --   54.00  75.00 -39.69   99
 25  ω     24.00 124.00   1.00    8.00    --   54.00  77.00 150.00  100
 26  ω     28.00 123.00   1.00    8.00    --   54.00  70.00-110.30   95
 27  ω      1.00  96.00   1.00    8.00    --   54.00 -99.00-180.00   95
 28  ω     23.00 111.00   1.00    8.00    --   54.00-125.00 -60.00   88
 29  ω     23.00  49.00   1.00    8.00    --   54.00  78.00-131.84   26
 30  ω     24.00 124.00   1.00    8.00    --   54.00  77.00   0.00  100
 31  ω     37.00 127.00   1.00    8.00    --   58.00  58.00   1.64   90
 32  ω     28.00 128.00   1.00    8.00    --   58.00  77.00-167.07  100
 33  ω     37.00 127.00   1.00    8.00    --   58.00  58.00  75.63   90
 34  ω     40.00 132.00   1.00    8.00    --   62.00  49.00   3.94   92
 35  ω     33.00 132.00   1.00    8.00    --   62.00  76.00 -59.27   99
 36  ω     42.00 138.00   1.00    8.00    --   66.00  43.00-134.33   96
 37  ω     44.00 136.00   1.00    8.00    --   66.00  51.00 -24.14   92
 38  ω     45.00 135.00   1.00    8.00    --   66.00  56.00-103.87   90
 39  ω     45.00 135.00   1.00    8.00    --   66.00  57.00 -31.04   90
 40  ω     37.00 136.00   1.00    8.00    --   66.00  75.00-104.96   99
 41  ω     44.00 136.00   1.00    8.00    --   66.00  50.00 160.07   92
 42  ω     45.00 135.00   1.00    8.00    --   66.00  54.00  36.51   90
 43  ω     43.00 139.00   1.00    8.00    --   70.00  71.00-109.32   96
 44  ω     49.00 139.00   1.00    8.00    --   70.00  54.00  78.88   90
 45  ω     49.00 139.00   1.00    8.00    --   70.00  54.00-147.95   90
 46  ω     44.00 142.00   1.00    8.00    --   70.00  38.00   1.51   98
 47  ω     52.00 142.00   1.00    8.00    --   74.00  63.00  88.02   90
 48  ω     53.00 144.00   1.00    8.00    --   74.00  53.00 -87.18   91
 49  ω     52.00 147.00   1.00    8.00    --   78.00  70.00 -15.81   95
 50  ω     57.00 148.00   1.00    8.00    --   78.00  52.00  56.69   91
 51  ω     61.00 158.00   1.00   16.00    --   86.00  40.00  48.89   97
 52  ω     63.00 157.00   1.00   16.00    --   86.00  47.00  73.86   94
 53  ω     68.00 158.00   1.00   16.00    --   90.00  63.00 135.85   90
 54  ω     62.00 160.00   1.00   16.00    --   90.00  74.00 -33.21   98
 55  ω     60.00 160.00   1.00   16.00    --   90.00  77.00-155.70  100
 56  ω     65.00 164.00   1.00   16.00    --   94.00  76.00-133.70   99
 57  ω     71.00 167.00   1.00   16.00    --   98.00  72.00 -84.07   96
 58  ω     68.00 168.00   1.00   16.00    --   98.00  77.00 -20.38  100
 59  ω     85.00 175.00   1.00   16.00    --  108.00  64.00 150.00   90
 60  ω     78.00 178.00   1.00   16.00    --  108.00  77.00  60.00  100
 61  ω     78.00 178.00   1.00   16.00    --  108.00  77.00 -60.00  100
 62  ω     36.00 145.00   1.00   16.00    --  108.00 -92.00-120.00  109
 63  ω    107.00 145.00   1.00   16.00    --  108.00 -92.00-120.00   38
 64  ω     78.00 105.00   1.00   16.00    --  108.00  77.00  30.00   27
 65  ω     83.00 112.00   1.00   16.00    --  108.00  38.00 120.00   29
 66  ω     83.00 130.00   1.00   16.00    --  108.00  38.00  90.00   47
 67  ω     85.00 156.00   1.00   16.00    --  108.00  38.00 -30.00   71
 68  ω     82.00 109.00   1.00   16.00    --  108.00  38.00 -60.00   27
 69  ω     87.00 114.00   1.00   16.00    --  108.00  50.00-180.00   27
 70  ω     39.00 111.00   1.00   16.00    --  108.00-111.00-150.00   72
 71  ω     85.00 175.00   1.00   16.00    --  108.00  64.00  30.00   90
 72  ω     61.00 101.00   1.00   16.00    --  108.00 -38.00-120.00   40
 73  ω     36.00 146.00   1.00   16.00    --  108.00 -92.00  30.00  110
 74  ω     82.00 158.00   1.00   16.00    --  108.00  77.00-120.00   76
 75  ω     79.00 116.00   1.00   16.00    --  108.00-111.00 -60.00   37
 76  ω     47.00  74.00   1.00   16.00    --  108.00-111.00 -60.00   27
 77  ω     85.00 112.00   1.00   16.00    --  108.00  64.00  90.00   27
 78  ω     86.00 111.00   1.00   16.00    --  108.00  64.00-180.00   25
 79  ω     86.00 111.00   1.00   16.00    --  108.00  65.00  -6.69   25
 80  ω     86.00 111.00   1.00   16.00    --  108.00  64.00 -60.00   25
 81  ω    100.00 175.00   1.00   16.00    --  108.00 111.00  60.00   75
 82  ω     87.00 112.00   1.00   16.00    --  108.00  64.00  60.00   25
 83  ω     87.00 173.00   1.00   16.00    --  108.00  64.00 120.00   86
 84  ω     97.00 124.00   1.00   16.00    --  108.00  50.00 150.00   27
 85  ω    112.00 177.00   1.00   16.00    --  108.00  77.00 -90.00   65
 86  ω     79.00 106.00   1.00   16.00    --  108.00  77.00 -90.00   27
 87  ω     85.00 112.00   1.00   16.00    --  108.00  64.00-120.00   27
 88  ω     82.00 177.00   1.00   16.00    --  108.00  77.00 -30.00   95
 89  ω     70.00 129.00   1.00   16.00    --  108.00 -64.00   0.00   59
 90  ω     78.00 177.00   1.00   16.00    --  108.00  77.00-150.00   99
 91  ω     78.00 104.00   1.00   16.00    --  108.00  77.00  90.00   26
 92  ω     78.00 154.00   1.00   16.00    --  108.00  77.00   0.00   76
 93  ω     83.00 110.00   1.00   16.00    --  108.00  77.00 120.00   27
 94  ω     78.00 170.00   1.00   16.00    --  108.00  77.00-180.00   92
 95  ω     91.00 118.00   1.00   16.00    --  108.00  77.00 150.00   27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'Agilent Agilent SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0071987000
_diffrn_orient_matrix_UB_12      -0.1402189000
_diffrn_orient_matrix_UB_13      0.0828420000
_diffrn_orient_matrix_UB_21      0.1291246000
_diffrn_orient_matrix_UB_22      0.0089214000
_diffrn_orient_matrix_UB_23      0.0515790000
_diffrn_orient_matrix_UB_31      -0.0691899000
_diffrn_orient_matrix_UB_32      0.0467168000
_diffrn_orient_matrix_UB_33      0.0910179000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'microfocus X-Ray tube'
_diffrn_source_type              'Agilent Agilent SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4275
_reflns_number_total             5175
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  
'encif (Wadepohl, 2009-17); encifer 1.5.2 (CCDC, 2016)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_shelxl_version_number           2017/1
_computing_structure_solution    'SUPERFLIP (Palatinus, 2007-2009)'
_refine_diff_density_max         1.130
_refine_diff_density_min         -0.829
_refine_diff_density_rms         0.092
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         5175
_refine_ls_number_restraints     51
_refine_ls_R_factor_all          0.0644
_refine_ls_R_factor_gt           0.0515
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0674P)²+2.7305P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1353
_refine_ls_wR_factor_ref         0.1438
_refine_special_details          
;
Hydrogen atoms of solvent water were placed to maximize
hydrogen bonding (Nardelli, 1982) and refined riding.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups, All O(H,H) groups
2. Rigid body (RIGU) restrains
 N7, N8, C19, C20, C21, C22, C23, C24
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Riding coordinates:
 N8(H8A,H8B), O1(H1A,H1B)
3.b Secondary CH2 refined with riding coordinates:
 N2(H2A,H2B), N4(H4A,H4B), N6(H6A,H6B), C6(H6C,H6D), C12(H12A,H12B), C18(H18A,
 H18B), C24(H24A,H24B)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11), C14(H14),
 C15(H15), C16(H16), C17(H17), C20(H20), C21(H21), C22(H22), C23(H23)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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
Cu Cu 0.38189(4) 0.29094(4) 0.27079(4) 0.02289(16) Uani 1 1 d . . . . .
N1 N 0.4196(3) 0.1150(3) 0.2008(3) 0.0327(7) Uani 1 1 d . . . . .
N2 N 0.5733(3) 0.2765(3) 0.2435(2) 0.0267(6) Uani 1 1 d . . . . .
H2A H 0.597077 0.356310 0.221261 0.032 Uiso 1 1 calc R . . . .
H2B H 0.616979 0.227777 0.311352 0.032 Uiso 1 1 calc R . . . .
N3 N 0.1867(3) 0.3080(3) 0.2593(2) 0.0256(6) Uani 1 1 d . . . . .
N4 N 0.3501(3) 0.4426(3) 0.1215(2) 0.0247(6) Uani 1 1 d . . . . .
H4A H 0.407120 0.497548 0.117913 0.030 Uiso 1 1 calc R . . . .
H4B H 0.361101 0.415014 0.060402 0.030 Uiso 1 1 calc R . . . .
N5 N 0.3712(3) 0.4243(3) 0.3861(2) 0.0259(6) Uani 1 1 d . . . . .
N6 N 0.4055(3) 0.1660(3) 0.4374(2) 0.0258(6) Uani 1 1 d . . . . .
H6A H 0.373861 0.093073 0.441275 0.031 Uiso 1 1 calc R . . . .
H6B H 0.490342 0.144107 0.456562 0.031 Uiso 1 1 calc R . . . .
C1 C 0.5385(4) 0.1060(3) 0.1673(3) 0.0317(8) Uani 1 1 d . . . . .
C2 C 0.5950(4) 0.0004(4) 0.1422(3) 0.0406(10) Uani 1 1 d . . . . .
H2 H 0.681230 -0.005534 0.121336 0.049 Uiso 1 1 calc R . . . .
C3 C 0.5235(5) -0.0967(4) 0.1481(4) 0.0478(11) Uani 1 1 d . . . . .
H3 H 0.559657 -0.169447 0.130100 0.057 Uiso 1 1 calc R . . . .
C4 C 0.4000(5) -0.0859(4) 0.1803(3) 0.0448(11) Uani 1 1 d . . . . .
H4 H 0.348719 -0.150287 0.183645 0.054 Uiso 1 1 calc R . . . .
C5 C 0.3518(4) 0.0196(4) 0.2077(3) 0.0395(9) Uani 1 1 d . . . . .
H5 H 0.267178 0.025415 0.232538 0.047 Uiso 1 1 calc R . . . .
C6 C 0.6082(4) 0.2189(3) 0.1545(3) 0.0327(8) Uani 1 1 d . . . . .
H6C H 0.701102 0.190028 0.161305 0.039 Uiso 1 1 calc R . . . .
H6D H 0.587309 0.284739 0.076623 0.039 Uiso 1 1 calc R . . . .
C7 C 0.1317(3) 0.4190(3) 0.1799(3) 0.0274(7) Uani 1 1 d . . . . .
C8 C 0.0005(4) 0.4478(4) 0.1623(3) 0.0379(9) Uani 1 1 d . . . . .
H8 H -0.036811 0.525730 0.104535 0.046 Uiso 1 1 calc R . . . .
C9 C -0.0755(4) 0.3626(5) 0.2292(4) 0.0441(10) Uani 1 1 d . . . . .
H9 H -0.165562 0.381890 0.219332 0.053 Uiso 1 1 calc R . . . .
C10 C -0.0190(4) 0.2492(4) 0.3104(4) 0.0423(10) Uani 1 1 d . . . . .
H10 H -0.069496 0.189147 0.357500 0.051 Uiso 1 1 calc R . . . .
C11 C 0.1120(3) 0.2241(4) 0.3226(3) 0.0316(8) Uani 1 1 d . . . . .
H11 H 0.150911 0.144866 0.377487 0.038 Uiso 1 1 calc R . . . .
C12 C 0.2195(3) 0.5104(3) 0.1145(3) 0.0306(8) Uani 1 1 d . . . . .
H12A H 0.188638 0.550419 0.032305 0.037 Uiso 1 1 calc R . . . .
H12B H 0.219831 0.579549 0.147163 0.037 Uiso 1 1 calc R . . . .
C13 C 0.3454(3) 0.3568(3) 0.4949(3) 0.0261(7) Uani 1 1 d . . . . .
C14 C 0.3209(4) 0.4137(4) 0.5773(3) 0.0356(9) Uani 1 1 d . . . . .
H14 H 0.304898 0.363444 0.654293 0.043 Uiso 1 1 calc R . . . .
C15 C 0.3201(4) 0.5443(4) 0.5463(4) 0.0385(9) Uani 1 1 d . . . . .
H15 H 0.301580 0.585382 0.601366 0.046 Uiso 1 1 calc R . . . .
C16 C 0.3463(4) 0.6147(4) 0.4348(3) 0.0330(8) Uani 1 1 d . . . . .
H16 H 0.346361 0.704875 0.411476 0.040 Uiso 1 1 calc R . . . .
C17 C 0.3724(3) 0.5512(3) 0.3578(3) 0.0287(8) Uani 1 1 d . . . . .
H17 H 0.392257 0.599371 0.281270 0.034 Uiso 1 1 calc R . . . .
C18 C 0.3441(4) 0.2148(4) 0.5244(3) 0.0336(8) Uani 1 1 d . . . . .
H18A H 0.388789 0.167906 0.600872 0.040 Uiso 1 1 calc R . . . .
H18B H 0.254874 0.197395 0.530398 0.040 Uiso 1 1 calc R . . . .
N7 N 0.8992(5) 0.1930(5) -0.1420(6) 0.0846(15) Uani 1 1 d . U . . .
N8 N 0.9598(7) 0.1970(9) -0.3679(7) 0.127(3) Uani 1 1 d . U . . .
H8A H 0.950768 0.227515 -0.446583 0.153 Uiso 1 1 d R . . . .
H8B H 0.885658 0.171155 -0.337553 0.153 Uiso 1 1 d R . . . .
C19 C 1.0019(6) 0.2385(7) -0.1967(5) 0.0730(16) Uani 1 1 d . U . . .
C20 C 1.1098(6) 0.2392(6) -0.1401(6) 0.0805(18) Uani 1 1 d . U . . .
H20 H 1.181865 0.267018 -0.182167 0.097 Uiso 1 1 calc R . . . .
C21 C 1.1156(8) 0.2000(6) -0.0223(6) 0.090(2) Uani 1 1 d . U . . .
H21 H 1.190237 0.203842 0.018162 0.108 Uiso 1 1 calc R . . . .
C22 C 1.0150(11) 0.1559(7) 0.0359(6) 0.108(3) Uani 1 1 d . U . . .
H22 H 1.016280 0.128543 0.118004 0.130 Uiso 1 1 calc R . . . .
C23 C 0.9088(9) 0.1513(6) -0.0272(8) 0.098(2) Uani 1 1 d . U . . .
H23 H 0.838857 0.116254 0.014084 0.118 Uiso 1 1 calc R . . . .
C24 C 0.9880(7) 0.2956(9) -0.3307(6) 0.094(2) Uani 1 1 d . U . . .
H24A H 0.918632 0.369311 -0.356093 0.113 Uiso 1 1 calc R . . . .
H24B H 1.068170 0.325713 -0.363124 0.113 Uiso 1 1 calc R . . . .
O1 O 0.1514(5) -0.0021(5) 0.7133(4) 0.1012(15) Uani 1 1 d . . . . .
H1A H 0.084153 0.068862 0.681098 0.121 Uiso 1 1 d R . . . .
H1B H 0.185383 -0.027458 0.651258 0.121 Uiso 1 1 d R . . . .
Cl1 Cl 0.39037(8) 0.41787(8) -0.12761(7) 0.0290(2) Uani 1 1 d . . . . .
Cl2 Cl 0.27555(8) 0.90229(8) 0.51067(7) 0.0301(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
Cu N1 2.399(3) . ?
Cu N2 2.052(3) . ?
Cu N3 2.055(3) . ?
Cu N4 2.016(3) . ?
Cu N5 2.385(3) . ?
Cu N6 2.038(3) . ?
N1 C1 1.330(5) . ?
N1 C5 1.345(5) . ?
N2 H2A 0.9100 . ?
N2 H2B 0.9100 . ?
N2 C6 1.478(5) . ?
N3 C7 1.345(4) . ?
N3 C11 1.345(4) . ?
N4 H4A 0.9100 . ?
N4 H4B 0.9100 . ?
N4 C12 1.475(5) . ?
N5 C13 1.340(4) . ?
N5 C17 1.344(4) . ?
N6 H6A 0.9100 . ?
N6 H6B 0.9100 . ?
N6 C18 1.477(5) . ?
C1 C2 1.385(5) . ?
C1 C6 1.511(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.390(6) . ?
C3 H3 0.9500 . ?
C3 C4 1.371(7) . ?
C4 H4 0.9500 . ?
C4 C5 1.374(6) . ?
C5 H5 0.9500 . ?
C6 H6C 0.9900 . ?
C6 H6D 0.9900 . ?
C7 C8 1.386(5) . ?
C7 C12 1.500(5) . ?
C8 H8 0.9500 . ?
C8 C9 1.379(6) . ?
C9 H9 0.9500 . ?
C9 C10 1.375(6) . ?
C10 H10 0.9500 . ?
C10 C11 1.379(5) . ?
C11 H11 0.9500 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.382(5) . ?
C13 C18 1.506(5) . ?
C14 H14 0.9500 . ?
C14 C15 1.377(6) . ?
C15 H15 0.9500 . ?
C15 C16 1.377(6) . ?
C16 H16 0.9500 . ?
C16 C17 1.377(5) . ?
C17 H17 0.9500 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
N7 C19 1.345(8) . ?
N7 C23 1.326(10) . ?
N8 H8A 0.9100 . ?
N8 H8B 0.9100 . ?
N8 C24 1.400(10) . ?
C19 C20 1.343(8) . ?
C19 C24 1.549(9) . ?
C20 H20 0.9500 . ?
C20 C21 1.362(9) . ?
C21 H21 0.9500 . ?
C21 C22 1.339(12) . ?
C22 H22 0.9500 . ?
C22 C23 1.386(12) . ?
C23 H23 0.9500 . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
O1 H1A 0.9638 . ?
O1 H1B 0.9580 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Cu N1 76.48(11) . . ?
N2 Cu N3 166.89(12) . . ?
N2 Cu N5 99.31(11) . . ?
N3 Cu N1 95.66(11) . . ?
N3 Cu N5 90.90(11) . . ?
N4 Cu N1 101.59(11) . . ?
N4 Cu N2 89.60(11) . . ?
N4 Cu N3 81.64(11) . . ?
N4 Cu N5 92.91(11) . . ?
N4 Cu N6 167.99(12) . . ?
N5 Cu N1 164.80(10) . . ?
N6 Cu N1 90.39(11) . . ?
N6 Cu N2 93.97(11) . . ?
N6 Cu N3 96.58(11) . . ?
N6 Cu N5 75.21(11) . . ?
C1 N1 Cu 108.9(2) . . ?
C1 N1 C5 118.6(3) . . ?
C5 N1 Cu 131.6(3) . . ?
Cu N2 H2A 109.0 . . ?
Cu N2 H2B 109.0 . . ?
H2A N2 H2B 107.8 . . ?
C6 N2 Cu 112.8(2) . . ?
C6 N2 H2A 109.0 . . ?
C6 N2 H2B 109.0 . . ?
C7 N3 Cu 113.5(2) . . ?
C11 N3 Cu 127.6(2) . . ?
C11 N3 C7 118.9(3) . . ?
Cu N4 H4A 109.6 . . ?
Cu N4 H4B 109.6 . . ?
H4A N4 H4B 108.1 . . ?
C12 N4 Cu 110.4(2) . . ?
C12 N4 H4A 109.6 . . ?
C12 N4 H4B 109.6 . . ?
C13 N5 Cu 109.8(2) . . ?
C13 N5 C17 118.1(3) . . ?
C17 N5 Cu 131.6(2) . . ?
Cu N6 H6A 108.5 . . ?
Cu N6 H6B 108.5 . . ?
H6A N6 H6B 107.5 . . ?
C18 N6 Cu 115.1(2) . . ?
C18 N6 H6A 108.5 . . ?
C18 N6 H6B 108.5 . . ?
N1 C1 C2 122.0(4) . . ?
N1 C1 C6 116.6(3) . . ?
C2 C1 C6 121.4(4) . . ?
C1 C2 H2 120.6 . . ?
C1 C2 C3 118.9(4) . . ?
C3 C2 H2 120.6 . . ?
C2 C3 H3 120.5 . . ?
C4 C3 C2 119.0(4) . . ?
C4 C3 H3 120.5 . . ?
C3 C4 H4 120.6 . . ?
C3 C4 C5 118.8(4) . . ?
C5 C4 H4 120.6 . . ?
N1 C5 C4 122.7(4) . . ?
N1 C5 H5 118.6 . . ?
C4 C5 H5 118.6 . . ?
N2 C6 C1 111.5(3) . . ?
N2 C6 H6C 109.3 . . ?
N2 C6 H6D 109.3 . . ?
C1 C6 H6C 109.3 . . ?
C1 C6 H6D 109.3 . . ?
H6C C6 H6D 108.0 . . ?
N3 C7 C8 121.3(3) . . ?
N3 C7 C12 116.4(3) . . ?
C8 C7 C12 122.3(3) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 C7 119.5(4) . . ?
C9 C8 H8 120.3 . . ?
C8 C9 H9 120.5 . . ?
C10 C9 C8 119.1(4) . . ?
C10 C9 H9 120.5 . . ?
C9 C10 H10 120.5 . . ?
C9 C10 C11 119.0(4) . . ?
C11 C10 H10 120.5 . . ?
N3 C11 C10 122.2(4) . . ?
N3 C11 H11 118.9 . . ?
C10 C11 H11 118.9 . . ?
N4 C12 C7 110.7(3) . . ?
N4 C12 H12A 109.5 . . ?
N4 C12 H12B 109.5 . . ?
C7 C12 H12A 109.5 . . ?
C7 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
N5 C13 C14 122.0(3) . . ?
N5 C13 C18 117.1(3) . . ?
C14 C13 C18 120.9(3) . . ?
C13 C14 H14 120.4 . . ?
C15 C14 C13 119.2(4) . . ?
C15 C14 H14 120.4 . . ?
C14 C15 H15 120.3 . . ?
C14 C15 C16 119.3(4) . . ?
C16 C15 H15 120.3 . . ?
C15 C16 H16 120.8 . . ?
C17 C16 C15 118.4(4) . . ?
C17 C16 H16 120.8 . . ?
N5 C17 C16 123.0(3) . . ?
N5 C17 H17 118.5 . . ?
C16 C17 H17 118.5 . . ?
N6 C18 C13 112.7(3) . . ?
N6 C18 H18A 109.1 . . ?
N6 C18 H18B 109.1 . . ?
C13 C18 H18A 109.1 . . ?
C13 C18 H18B 109.1 . . ?
H18A C18 H18B 107.8 . . ?
C23 N7 C19 116.0(7) . . ?
H8A N8 H8B 109.5 . . ?
C24 N8 H8A 108.9 . . ?
C24 N8 H8B 109.0 . . ?
N7 C19 C24 116.2(6) . . ?
C20 C19 N7 122.9(6) . . ?
C20 C19 C24 120.9(6) . . ?
C19 C20 H20 120.1 . . ?
C19 C20 C21 119.9(7) . . ?
C21 C20 H20 120.1 . . ?
C20 C21 H21 120.4 . . ?
C22 C21 C20 119.3(7) . . ?
C22 C21 H21 120.4 . . ?
C21 C22 H22 121.0 . . ?
C21 C22 C23 118.1(7) . . ?
C23 C22 H22 121.0 . . ?
N7 C23 C22 123.7(7) . . ?
N7 C23 H23 118.1 . . ?
C22 C23 H23 118.1 . . ?
N8 C24 C19 106.6(7) . . ?
N8 C24 H24A 110.4 . . ?
N8 C24 H24B 110.4 . . ?
C19 C24 H24A 110.4 . . ?
C19 C24 H24B 110.4 . . ?
H24A C24 H24B 108.6 . . ?
H1A O1 H1B 108.0 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1A N8 0.96 1.75 2.712(9) 176.2 1_456 yes

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
Cu N1 C1 C2 168.4(3) . . . . ?
Cu N1 C1 C6 -13.4(4) . . . . ?
Cu N1 C5 C4 -168.0(3) . . . . ?
Cu N2 C6 C1 -41.9(3) . . . . ?
Cu N3 C7 C8 -178.6(3) . . . . ?
Cu N3 C7 C12 -0.2(4) . . . . ?
Cu N3 C11 C10 176.9(3) . . . . ?
Cu N4 C12 C7 -29.1(3) . . . . ?
Cu N5 C13 C14 -173.2(3) . . . . ?
Cu N5 C13 C18 6.7(4) . . . . ?
Cu N5 C17 C16 170.0(3) . . . . ?
Cu N6 C18 C13 -34.4(4) . . . . ?
N1 C1 C2 C3 2.4(6) . . . . ?
N1 C1 C6 N2 36.1(4) . . . . ?
N3 C7 C8 C9 1.5(6) . . . . ?
N3 C7 C12 N4 19.5(4) . . . . ?
N5 C13 C14 C15 1.4(6) . . . . ?
N5 C13 C18 N6 15.7(5) . . . . ?
C1 N1 C5 C4 -0.8(6) . . . . ?
C1 C2 C3 C4 -1.0(6) . . . . ?
C2 C1 C6 N2 -145.7(3) . . . . ?
C2 C3 C4 C5 -1.1(6) . . . . ?
C3 C4 C5 N1 2.1(6) . . . . ?
C5 N1 C1 C2 -1.6(5) . . . . ?
C5 N1 C1 C6 176.7(3) . . . . ?
C6 C1 C2 C3 -175.7(4) . . . . ?
C7 N3 C11 C10 -1.4(6) . . . . ?
C7 C8 C9 C10 -1.4(6) . . . . ?
C8 C7 C12 N4 -162.1(3) . . . . ?
C8 C9 C10 C11 0.0(7) . . . . ?
C9 C10 C11 N3 1.5(6) . . . . ?
C11 N3 C7 C8 -0.1(5) . . . . ?
C11 N3 C7 C12 178.3(3) . . . . ?
C12 C7 C8 C9 -176.8(4) . . . . ?
C13 N5 C17 C16 -1.2(5) . . . . ?
C13 C14 C15 C16 -1.4(6) . . . . ?
C14 C13 C18 N6 -164.4(3) . . . . ?
C14 C15 C16 C17 0.1(6) . . . . ?
C15 C16 C17 N5 1.3(6) . . . . ?
C17 N5 C13 C14 -0.1(5) . . . . ?
C17 N5 C13 C18 179.8(3) . . . . ?
C18 C13 C14 C15 -178.5(4) . . . . ?
N7 C19 C20 C21 -4.1(11) . . . . ?
N7 C19 C24 N8 -59.5(8) . . . . ?
C19 N7 C23 C22 1.8(10) . . . . ?
C19 C20 C21 C22 2.8(11) . . . . ?
C20 C19 C24 N8 122.6(7) . . . . ?
C20 C21 C22 C23 0.5(11) . . . . ?
C21 C22 C23 N7 -2.9(11) . . . . ?
C23 N7 C19 C20 1.8(10) . . . . ?
C23 N7 C19 C24 -176.1(6) . . . . ?
C24 C19 C20 C21 173.6(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.304
_oxdiff_exptl_absorpt_empirical_full_min 0.827
_cell_oxdiff_length_a            10.6115(4)
_cell_oxdiff_length_b            11.2052(4)
_cell_oxdiff_length_c            12.3212(6)
_cell_oxdiff_angle_alpha         69.734(4)
_cell_oxdiff_angle_beta          89.956(3)
_cell_oxdiff_angle_gamma         82.315(3)
_cell_oxdiff_volume              1360.36(9)
_cell_oxdiff_measurement_reflns_used 13466
_symmetry_cell_setting           triclinic
#_space_group_name_H-M_alt       'P -1'
#_space_group_IT_number          2
_chemical_absolute_configuration .
_diffrn_measurement_specimen_support 'polyimid foil'
_diffrn_ambient_environment      'perfluoro polyether oil / N~2~'




