# 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. 
# 
#######################################################################

data_shelxl
_audit_block_doi                 10.5517/ccdc.csd.cc1p33c8
_database_code_depnum_ccdc_archive 'CCDC 1552119'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C8DT01424H 2018
_audit_update_record             
;
2018-05-05 deposited with the CCDC.
2018-11-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H15 Cl Cu N4'
_chemical_formula_weight         410.35

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'
N N 0.0061 0.0033 '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                   10.933(2)
_cell_length_b                   13.690(3)
_cell_length_c                   11.946(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.49(3)
_cell_angle_gamma                90
_cell_volume                     1779.8(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6590
_cell_measurement_theta_min      2.269
_cell_measurement_theta_max      25.992

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.531
_exptl_crystal_F_000             836
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_exptl_absorpt_coefficient_mu    1.388
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           synchrotron
_diffrn_source                   synchrotron
_diffrn_measurement_device_type  'ADSC Q210 CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6590
_diffrn_reflns_av_unetI/netI     0.1175
_diffrn_reflns_av_R_equivalents  0.0751
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.269
_diffrn_reflns_theta_max         25.992
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3493
_reflns_number_gt                2056
_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       'PAL BL2D-SMDC Program'
_computing_cell_refinement       'HKL3000sm (Otwinowski & Minor, 1997)'
_computing_data_reduction        'HKL3000sm (Otwinowski & Minor, 1997)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0524P)²] 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         3493
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1041
_refine_ls_R_factor_gt           0.0494
_refine_ls_wR_factor_ref         0.1152
_refine_ls_wR_factor_gt          0.1011
_refine_ls_goodness_of_fit_ref   0.912
_refine_ls_restrained_S_all      0.912
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.54256(5) 0.25324(4) 0.34677(4) 0.01933(16) Uani 1 1 d . . . . .
Cl1 Cl 0.54756(11) 0.10513(9) 0.25477(10) 0.0276(3) Uani 1 1 d . . . . .
N1 N 0.5647(3) 0.7657(3) 0.5190(3) 0.0180(8) Uani 1 1 d . . . . .
N2 N 0.4000(3) 0.3308(3) 0.2597(3) 0.0195(8) Uani 1 1 d . . . . .
C1 C 0.4242(4) 0.6692(3) 0.2600(3) 0.0241(10) Uani 0.2 1 d . . P A 1
H005 H 0.3774 0.6958 0.3157 0.029 Uiso 0.2 1 calc R U P A 1
N3 N 0.6938(4) 0.3236(3) 0.3899(3) 0.0236(9) Uani 1 1 d . . . . .
C2 C 0.4927(4) 0.5891(3) 0.2796(3) 0.0178(10) Uani 1 1 d . . . . .
C3 C 0.4363(4) 0.4546(3) 0.4074(3) 0.0154(9) Uani 1 1 d . . . . .
C4 C 0.4954(4) 0.5442(3) 0.3948(3) 0.0165(9) Uani 1 1 d . . . . .
C5 C 0.2237(4) 0.3368(3) 0.1246(4) 0.0241(11) Uani 1 1 d . . . . .
H00A H 0.1790 0.3090 0.0603 0.029 Uiso 1 1 calc R U . . .
C6 C 0.3319(4) 0.2953(3) 0.1706(4) 0.0218(10) Uani 1 1 d . . . . .
H00B H 0.3596 0.2377 0.1365 0.026 Uiso 1 1 calc R U . . .
C7 C 0.7080(4) 0.7005(4) 0.3994(4) 0.0195(10) Uani 1 1 d . . . . .
H00C H 0.7445 0.6450 0.3684 0.023 Uiso 1 1 calc R U . . .
C8 C 0.2514(4) 0.4585(3) 0.2671(3) 0.0188(10) Uani 1 1 d . . . . .
H00D H 0.2251 0.5160 0.3024 0.023 Uiso 1 1 calc R U . . .
C9 C 0.3593(4) 0.4131(3) 0.3083(3) 0.0164(10) Uani 1 1 d . . . . .
C10 C 0.6033(4) 0.8557(3) 0.4948(4) 0.0210(10) Uani 1 1 d . . . . .
H00F H 0.5675 0.9101 0.5289 0.025 Uiso 1 1 calc R U . . .
C11 C 0.5579(4) 0.5911(3) 0.4871(3) 0.0166(9) Uani 1 1 d . . . . .
C12 C 0.6146(4) 0.6889(3) 0.4683(3) 0.0158(10) Uani 1 1 d . . . . .
C13 C 0.7482(4) 0.7934(3) 0.3758(4) 0.0207(10) Uani 1 1 d . . . . .
H00I H 0.8124 0.8026 0.3286 0.025 Uiso 1 1 calc R U . . .
C14 C 0.1816(4) 0.4205(3) 0.1748(4) 0.0225(11) Uani 1 1 d . . . . .
H00J H 0.1068 0.4508 0.1463 0.027 Uiso 1 1 calc R U . . .
N4 N 0.5603(4) 0.5468(3) 0.1993(3) 0.0242(10) Uani 0.2 1 d . . P A 1
C15 C 0.7782(4) 0.3696(4) 0.4177(4) 0.0237(11) Uani 1 1 d . . . . .
C16 C 0.6924(4) 0.8730(4) 0.4228(4) 0.0249(11) Uani 1 1 d . . . . .
H00M H 0.7152 0.9379 0.4057 0.030 Uiso 1 1 calc R U . . .
C17 C 0.5597(4) 0.5928(4) 0.0972(4) 0.0278(11) Uani 1 1 d . . . . .
H00N H 0.6078 0.5675 0.0417 0.033 Uiso 1 1 calc R U . A 1
C18 C 0.4904(4) 0.6749(4) 0.0748(4) 0.0275(12) Uani 1 1 d . . . . .
H00O H 0.4878 0.7065 0.0038 0.033 Uiso 1 1 calc R U . . .
C19 C 0.4245(5) 0.7101(4) 0.1585(4) 0.0310(12) Uani 1 1 d . . . . .
H00P H 0.3762 0.7671 0.1433 0.037 Uiso 1 1 calc R U . A 1
C20 C 0.8848(5) 0.4308(4) 0.4526(4) 0.0397(14) Uani 1 1 d . . . . .
H00E H 0.9216 0.4542 0.3859 0.060 Uiso 1 1 calc R U . . .
H00G H 0.9455 0.3924 0.4996 0.060 Uiso 1 1 calc R U . . .
H00H H 0.8587 0.4867 0.4956 0.060 Uiso 1 1 calc R U . . .
C4A C 0.5603(4) 0.5468(3) 0.1993(3) 0.0242(10) Uani 0.8 1 d . . P A 2
H00K H 0.6053 0.4882 0.2147 0.029 Uiso 0.8 1 calc R U P A 2
C1A N 0.4242(4) 0.6692(3) 0.2600(3) 0.0241(10) Uani 0.8 1 d . . P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N3 1.940(4) . ?
Cu1 N2 2.080(4) . ?
Cu1 N1 2.091(3) 3_666 ?
Cu1 Cl1 2.3094(13) . ?
N1 C10 1.343(5) . ?
N1 C12 1.354(5) . ?
N1 Cu1 2.091(3) 3_666 ?
N2 C6 1.331(5) . ?
N2 C9 1.362(5) . ?
C1 C2 1.336(6) . ?
C1 C19 1.336(6) . ?
C1 H005 0.9500 . ?
N3 C15 1.140(6) . ?
C2 N4 1.391(6) . ?
C2 C4 1.505(6) . ?
C3 C4 1.400(6) . ?
C3 C11 1.404(6) 3_666 ?
C3 C9 1.498(6) . ?
C4 C11 1.397(6) . ?
C5 C6 1.378(6) . ?
C5 C14 1.392(6) . ?
C5 H00A 0.9500 . ?
C6 H00B 0.9500 . ?
C7 C12 1.381(6) . ?
C7 C13 1.383(6) . ?
C7 H00C 0.9500 . ?
C8 C14 1.381(6) . ?
C8 C9 1.382(6) . ?
C8 H00D 0.9500 . ?
C10 C16 1.381(6) . ?
C10 H00F 0.9500 . ?
C11 C3 1.404(6) 3_666 ?
C11 C12 1.501(6) . ?
C13 C16 1.394(6) . ?
C13 H00I 0.9500 . ?
C14 H00J 0.9500 . ?
N4 C17 1.373(6) . ?
C15 C20 1.463(6) . ?
C16 H00M 0.9500 . ?
C17 C18 1.368(6) . ?
C17 H00N 0.9500 . ?
C18 C19 1.374(6) . ?
C18 H00O 0.9500 . ?
C19 H00P 0.9500 . ?
C20 H00E 0.9800 . ?
C20 H00G 0.9800 . ?
C20 H00H 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 Cu1 N2 117.27(15) . . ?
N3 Cu1 N1 112.58(14) . 3_666 ?
N2 Cu1 N1 89.92(13) . 3_666 ?
N3 Cu1 Cl1 120.25(12) . . ?
N2 Cu1 Cl1 105.12(10) . . ?
N1 Cu1 Cl1 107.26(10) 3_666 . ?
C10 N1 C12 117.9(4) . . ?
C10 N1 Cu1 119.3(3) . 3_666 ?
C12 N1 Cu1 121.7(3) . 3_666 ?
C6 N2 C9 117.5(4) . . ?
C6 N2 Cu1 123.3(3) . . ?
C9 N2 Cu1 118.0(3) . . ?
C2 C1 C19 117.0(4) . . ?
C2 C1 H005 121.5 . . ?
C19 C1 H005 121.5 . . ?
C15 N3 Cu1 175.6(4) . . ?
C1 C2 N4 123.1(4) . . ?
C1 C2 C4 117.2(4) . . ?
N4 C2 C4 119.7(4) . . ?
C4 C3 C11 120.4(4) . 3_666 ?
C4 C3 C9 118.5(4) . . ?
C11 C3 C9 120.9(4) 3_666 . ?
C11 C4 C3 120.9(4) . . ?
C11 C4 C2 119.9(4) . . ?
C3 C4 C2 119.2(4) . . ?
C6 C5 C14 118.3(4) . . ?
C6 C5 H00A 120.8 . . ?
C14 C5 H00A 120.8 . . ?
N2 C6 C5 124.2(4) . . ?
N2 C6 H00B 117.9 . . ?
C5 C6 H00B 117.9 . . ?
C12 C7 C13 119.7(4) . . ?
C12 C7 H00C 120.1 . . ?
C13 C7 H00C 120.1 . . ?
C14 C8 C9 120.2(4) . . ?
C14 C8 H00D 119.9 . . ?
C9 C8 H00D 119.9 . . ?
N2 C9 C8 121.5(4) . . ?
N2 C9 C3 118.0(4) . . ?
C8 C9 C3 120.5(4) . . ?
N1 C10 C16 123.2(4) . . ?
N1 C10 H00F 118.4 . . ?
C16 C10 H00F 118.4 . . ?
C4 C11 C3 118.7(4) . 3_666 ?
C4 C11 C12 118.1(4) . . ?
C3 C11 C12 123.2(4) 3_666 . ?
N1 C12 C7 122.0(4) . . ?
N1 C12 C11 115.8(4) . . ?
C7 C12 C11 122.1(4) . . ?
C7 C13 C16 118.5(4) . . ?
C7 C13 H00I 120.8 . . ?
C16 C13 H00I 120.8 . . ?
C8 C14 C5 118.3(4) . . ?
C8 C14 H00J 120.9 . . ?
C5 C14 H00J 120.9 . . ?
C17 N4 C2 117.7(4) . . ?
N3 C15 C20 178.6(5) . . ?
C10 C16 C13 118.6(4) . . ?
C10 C16 H00M 120.7 . . ?
C13 C16 H00M 120.7 . . ?
C18 C17 N4 120.4(4) . . ?
C18 C17 H00N 119.8 . . ?
N4 C17 H00N 119.8 . . ?
C17 C18 C19 117.7(4) . . ?
C17 C18 H00O 121.1 . . ?
C19 C18 H00O 121.1 . . ?
C1 C19 C18 124.0(5) . . ?
C1 C19 H00P 118.0 . . ?
C18 C19 H00P 118.0 . . ?
C15 C20 H00E 109.5 . . ?
C15 C20 H00G 109.5 . . ?
H00E C20 H00G 109.5 . . ?
C15 C20 H00H 109.5 . . ?
H00E C20 H00H 109.5 . . ?
H00G C20 H00H 109.5 . . ?

_refine_diff_density_max         0.444
_refine_diff_density_min         -0.915
_refine_diff_density_rms         0.117

_shelxl_version_number           2014-3

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

data_p21n70
_database_code_depnum_ccdc_archive 'CCDC 1874373'
_audit_update_record             
;
2018-11-12 deposited with the CCDC.
2018-11-21 downloaded from the CCDC.
;
_audit_creation_date             2018-11-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C40 H24 Cl2 Cu2 F1.03 N8'
_chemical_formula_sum            'C40 H24 Cl2 Cu2 F1.02 N8'
_chemical_formula_weight         834.13
_chemical_melting_point          ?
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'

_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   10.939(2)
_cell_length_b                   13.812(3)
_cell_length_c                   11.949(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.75(3)
_cell_angle_gamma                90
_cell_volume                     1796.3(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    19538
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.508
_cell_measurement_theta_min      2.260
_shelx_estimated_absorpt_T_max   0.960
_shelx_estimated_absorpt_T_min   0.947
_exptl_absorpt_coefficient_mu    1.381
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       trapezoid
_exptl_crystal_F_000             842
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0665
_diffrn_reflns_av_unetI/netI     0.0454
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            19538
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.508
_diffrn_reflns_theta_min         2.260
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  Synchrotron
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   Synchrotron
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4947
_reflns_number_total             5369
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.769
_refine_diff_density_min         -0.928
_refine_diff_density_rms         0.164
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.357
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         5369
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0478
_refine_ls_restrained_S_all      1.357
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1677
_refine_ls_wR_factor_ref         0.1749
_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. Others
 Fixed Uiso: F1(0.04) F2(0.04) F3(0.04)
3.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C12(H12), C13(H13), C14(H14), C15(H15), C17(H17),
 C19(H19)
3.b Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.45937(2) 0.25603(2) 0.65490(2) 0.02639(12) Uani 1 1 d . . . . .
Cl1 Cl 0.45641(5) 0.10955(4) 0.74726(5) 0.04199(17) Uani 1 1 d . . . . .
N1 N 0.56600(17) 0.23695(11) 0.52059(15) 0.0247(3) Uani 1 1 d . . . . .
N2 N 0.60176(15) 0.33407(12) 0.74029(12) 0.0260(3) Uani 1 1 d . . . . .
N3 N 0.57602(17) 0.67179(13) 0.73587(14) 0.0321(4) Uani 1 1 d . . . . .
N4 N 0.30842(16) 0.32562(13) 0.61186(14) 0.0293(3) Uani 1 1 d . . . . .
C1 C 0.51042(17) 0.59014(13) 0.71928(14) 0.0235(3) Uani 1 1 d . . . . .
C2 C 0.50677(17) 0.54461(12) 0.60536(13) 0.0225(3) Uani 1 1 d . . . . .
C3 C 0.56492(17) 0.45520(12) 0.59279(13) 0.0228(3) Uani 1 1 d . . . . .
C4 C 0.55808(16) 0.40978(12) 0.48769(13) 0.0216(3) Uani 1 1 d . . . . .
C5 C 0.64259(17) 0.41478(13) 0.69231(14) 0.0236(3) Uani 1 1 d . . . . .
C6 C 0.2243(2) 0.37215(15) 0.58456(17) 0.0330(4) Uani 1 1 d . . . . .
C7 C 0.61446(16) 0.31309(13) 0.47041(13) 0.0223(3) Uani 1 1 d . . . . .
C8 C 0.8206(2) 0.42345(16) 0.82622(17) 0.0329(4) Uani 1 1 d . . . . .
H8 H 0.895810 0.453070 0.854413 0.039 Uiso 1 1 calc R . . . .
C9 C 0.70788(16) 0.30178(16) 0.40045(14) 0.0266(4) Uani 1 1 d . . . . .
H9 H 0.743281 0.356691 0.368297 0.032 Uiso 1 1 calc R . . . .
C10 C 0.6698(2) 0.29929(16) 0.83132(16) 0.0318(4) Uani 1 1 d . . . . .
H10 H 0.641982 0.242688 0.866181 0.038 Uiso 1 1 calc R . . . .
C11 C 0.7783(2) 0.34164(17) 0.87704(16) 0.0356(4) Uani 1 1 d . . . . .
C12 C 0.6066(2) 0.14827(15) 0.49853(18) 0.0316(4) Uani 1 1 d . . . . .
H12 H 0.573193 0.094489 0.534557 0.038 Uiso 1 1 calc R . . . .
C13 C 0.4451(2) 0.54892(15) 0.80026(16) 0.0317(4) Uani 1 1 d . . . . .
H13 H 0.401587 0.489971 0.785932 0.038 Uiso 1 1 calc R . . . .
C14 C 0.75020(18) 0.46139(14) 0.73271(16) 0.0281(4) Uani 1 1 d . . . . .
H14 H 0.775688 0.518439 0.697178 0.034 Uiso 1 1 calc R . . . .
C15 C 0.5771(2) 0.71503(19) 0.8370(2) 0.0394(5) Uani 1 1 d . . . . .
H15 H 0.625044 0.771885 0.851105 0.047 Uiso 1 1 calc R . . . .
C16 C 0.5111(2) 0.67988(18) 0.92098(17) 0.0361(4) Uani 1 1 d . . . . .
C17 C 0.7483(2) 0.20991(18) 0.37848(16) 0.0329(4) Uani 1 1 d . . . . .
H17 H 0.812213 0.200770 0.331242 0.039 Uiso 1 1 calc R . . . .
C18 C 0.6949(2) 0.13114(17) 0.42587(19) 0.0358(4) Uani 1 1 d . . . . .
C19 C 0.4446(2) 0.59535(18) 0.90234(17) 0.0370(5) Uani 1 1 d . . . . .
H19 H 0.399106 0.569581 0.959127 0.044 Uiso 1 1 calc R . . . .
C20 C 0.1196(3) 0.4333(2) 0.5509(2) 0.0523(7) Uani 1 1 d . . . . .
H20A H 0.082205 0.413196 0.476588 0.078 Uiso 1 1 calc GR . . . .
H20B H 0.146652 0.500814 0.547568 0.078 Uiso 1 1 calc GR . . . .
H20C H 0.059169 0.427374 0.605733 0.078 Uiso 1 1 calc GR . . . .
F1 F 0.7403(6) 0.0521(5) 0.4169(6) 0.040 Uiso 0.210(4) 1 d . . . . .
F2 F 0.5067(8) 0.7358(5) 1.0044(7) 0.040 Uiso 0.192(4) 1 d . . . . .
F3 F 0.8248(11) 0.3132(10) 0.9606(10) 0.040 Uiso 0.110(4) 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 Cl1 2.3063(6) . ?
Cu1 N1 2.0929(19) . ?
Cu1 N2 2.0762(18) . ?
Cu1 N4 1.9352(17) . ?
N1 C7 1.345(2) . ?
N1 C12 1.338(2) . ?
N2 C5 1.350(2) . ?
N2 C10 1.344(2) . ?
N3 C1 1.341(2) . ?
N3 C15 1.347(3) . ?
N4 C6 1.143(3) . ?
C1 C2 1.496(2) . ?
C1 C13 1.382(3) . ?
C2 C3 1.404(2) . ?
C2 C4 1.407(2) 3_666 ?
C3 C4 1.399(2) . ?
C3 C5 1.498(2) . ?
C4 C2 1.407(2) 3_666 ?
C4 C7 1.494(2) . ?
C5 C14 1.385(3) . ?
C6 C20 1.447(3) . ?
C7 C9 1.392(2) . ?
C8 H8 0.9500 . ?
C8 C11 1.384(3) . ?
C8 C14 1.394(3) . ?
C9 H9 0.9500 . ?
C9 C17 1.378(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.386(3) . ?
C11 F3 1.143(13) . ?
C12 H12 0.9500 . ?
C12 C18 1.382(3) . ?
C13 H13 0.9500 . ?
C13 C19 1.379(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C15 C16 1.381(3) . ?
C16 C19 1.382(3) . ?
C16 F2 1.266(8) . ?
C17 H17 0.9500 . ?
C17 C18 1.383(3) . ?
C18 F1 1.208(7) . ?
C19 H19 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Cu1 Cl1 106.99(5) . . ?
N2 Cu1 Cl1 105.43(5) . . ?
N2 Cu1 N1 89.65(7) . . ?
N4 Cu1 Cl1 120.69(6) . . ?
N4 Cu1 N1 112.64(7) . . ?
N4 Cu1 N2 116.80(7) . . ?
C7 N1 Cu1 121.21(13) . . ?
C12 N1 Cu1 119.20(14) . . ?
C12 N1 C7 118.30(18) . . ?
C5 N2 Cu1 118.94(12) . . ?
C10 N2 Cu1 122.65(14) . . ?
C10 N2 C5 117.33(17) . . ?
C1 N3 C15 117.52(18) . . ?
C6 N4 Cu1 175.15(19) . . ?
N3 C1 C2 116.94(15) . . ?
N3 C1 C13 123.34(17) . . ?
C13 C1 C2 119.69(16) . . ?
C3 C2 C1 119.73(14) . . ?
C3 C2 C4 120.49(15) . 3_666 ?
C4 C2 C1 119.75(15) 3_666 . ?
C2 C3 C5 118.02(15) . . ?
C4 C3 C2 120.43(15) . . ?
C4 C3 C5 121.35(15) . . ?
C2 C4 C7 118.27(15) 3_666 . ?
C3 C4 C2 119.08(15) . 3_666 ?
C3 C4 C7 122.63(14) . . ?
N2 C5 C3 117.34(16) . . ?
N2 C5 C14 122.79(16) . . ?
C14 C5 C3 119.86(16) . . ?
N4 C6 C20 178.5(3) . . ?
N1 C7 C4 116.78(15) . . ?
N1 C7 C9 121.71(18) . . ?
C9 C7 C4 121.41(16) . . ?
C11 C8 H8 120.8 . . ?
C11 C8 C14 118.47(19) . . ?
C14 C8 H8 120.8 . . ?
C7 C9 H9 120.4 . . ?
C17 C9 C7 119.11(18) . . ?
C17 C9 H9 120.4 . . ?
N2 C10 H10 118.3 . . ?
N2 C10 C11 123.46(19) . . ?
C11 C10 H10 118.3 . . ?
C8 C11 C10 118.84(18) . . ?
F3 C11 C8 121.6(7) . . ?
F3 C11 C10 119.2(7) . . ?
N1 C12 H12 118.4 . . ?
N1 C12 C18 123.2(2) . . ?
C18 C12 H12 118.4 . . ?
C1 C13 H13 120.8 . . ?
C19 C13 C1 118.43(19) . . ?
C19 C13 H13 120.8 . . ?
C5 C14 C8 119.10(18) . . ?
C5 C14 H14 120.5 . . ?
C8 C14 H14 120.5 . . ?
N3 C15 H15 118.7 . . ?
N3 C15 C16 122.5(2) . . ?
C16 C15 H15 118.7 . . ?
C15 C16 C19 119.00(19) . . ?
F2 C16 C15 115.0(4) . . ?
F2 C16 C19 125.5(4) . . ?
C9 C17 H17 120.3 . . ?
C9 C17 C18 119.33(19) . . ?
C18 C17 H17 120.3 . . ?
C12 C18 C17 118.2(2) . . ?
F1 C18 C12 122.0(4) . . ?
F1 C18 C17 118.7(4) . . ?
C13 C19 C16 119.14(19) . . ?
C13 C19 H19 120.4 . . ?
C16 C19 H19 120.4 . . ?
C6 C20 H20A 109.5 . . ?
C6 C20 H20B 109.5 . . ?
C6 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
