# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_SMSP237_a
_database_code_depnum_ccdc_archive 'CCDC 2107292'
loop_
_audit_author_name
_audit_author_address
'Samit Pramanik'
;Jadavpur University
India
;
_audit_update_record             
;
2021-09-03 deposited with the CCDC.	2022-01-13 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         'C17 H13 Cl2 Cu N7'
_chemical_formula_sum            'C17 H13 Cl2 Cu N7'
_chemical_formula_weight         449.79

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   7.0900(5)
_cell_length_b                   15.0538(11)
_cell_length_c                   16.4613(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1756.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    3889
_cell_measurement_theta_min      2
_cell_measurement_theta_max      27.169

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.701
_exptl_crystal_F_000             908.0
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.09
_exptl_absorpt_coefficient_mu    1.566
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.769
_exptl_absorpt_correction_T_max  0.869
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD area-detector'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            60693
_diffrn_reflns_av_unetI/netI     0.0153
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.833
_diffrn_reflns_theta_max         27.169
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3883
_reflns_number_gt                3768
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.737
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    1.000

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

_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'APEX2(Bruker,2007)and SAINT (Bruker,2007)'
_computing_data_reduction        'SAINT(Bruker,2007)and XPREP(Bruker,2007)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    
;    
ORTEP-3 for Windows (Farrugia, 1997), DIAMOND (Brandenburg,
1999) and Mercury (Macrae et al., 2006)
;
_computing_publication_material  'PLATON (Spek, 2009)'
_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)+(0.1000P)²+0.2438P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1585 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.011(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3883
_refine_ls_number_parameters     288
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0265
_refine_ls_R_factor_gt           0.0223
_refine_ls_wR_factor_ref         0.0881
_refine_ls_wR_factor_gt          0.0756
_refine_ls_goodness_of_fit_ref   0.790
_refine_ls_restrained_S_all      0.790
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.24380(5) 0.58364(2) 0.79563(2) 0.02843(13) Uani 1 1 d . . . . .
Cl1 Cl 0.06877(13) 0.49361(5) 0.87445(5) 0.0417(2) Uani 1 1 d . . . . .
Cl2 Cl 0.54105(13) 0.60929(6) 0.85615(5) 0.0451(2) Uani 1 1 d . . . . .
N1 N 0.3083(4) 0.87508(16) 0.46001(15) 0.0287(5) Uani 1 1 d . . . . .
N2 N 0.2144(3) 0.74923(16) 0.40017(15) 0.0300(5) Uani 1 1 d . . . . .
N5 N 0.2480(3) 0.64980(15) 0.69287(13) 0.0246(4) Uani 1 1 d . . . . .
N7 N 0.0582(5) 0.88091(19) 0.86802(17) 0.0429(7) Uani 1 1 d . . . . .
C17 C 0.1988(4) 0.78405(18) 0.62049(17) 0.0262(5) Uani 1 1 d . . . . .
N3 N 0.4388(5) 0.36892(18) 0.59528(17) 0.0422(6) Uani 1 1 d . . . . .
N4 N 0.3243(4) 0.48561(16) 0.71635(15) 0.0285(5) Uani 1 1 d . . . . .
N6 N 0.1371(4) 0.70491(16) 0.83182(15) 0.0324(5) Uani 1 1 d . . . . .
C4 C 0.2579(4) 0.78796(17) 0.47018(15) 0.0249(5) Uani 1 1 d . . . . .
C5 C 0.2531(4) 0.74200(16) 0.54843(16) 0.0245(5) Uani 1 1 d . . . . .
C14 C 0.1010(5) 0.8558(2) 0.79275(19) 0.0349(6) Uani 1 1 d . . . . .
C16 C 0.1976(4) 0.73528(18) 0.69219(16) 0.0252(5) Uani 1 1 d . . . . .
C2 C 0.2947(5) 0.8916(2) 0.3782(2) 0.0354(6) Uani 1 1 d . . . . .
C15 C 0.1417(4) 0.76775(18) 0.77283(16) 0.0269(5) Uani 1 1 d . . . . .
C10 C 0.4181(5) 0.34339(19) 0.6725(2) 0.0365(7) Uani 1 1 d . . . . .
C1 C 0.3823(6) 0.9383(2) 0.5196(2) 0.0388(7) Uani 1 1 d . . . . .
C6 C 0.3007(4) 0.65134(17) 0.55028(16) 0.0249(5) Uani 1 1 d . . . . .
H6 H 0.333495 0.621454 0.502893 0.030 Uiso 1 1 calc R U . . .
C3 C 0.2372(5) 0.8144(2) 0.34307(18) 0.0353(6) Uani 1 1 d . . . . .
C13 C 0.0556(6) 0.8187(2) 0.9246(2) 0.0433(8) Uani 1 1 d . . . . .
C11 C 0.3619(5) 0.4009(2) 0.73387(19) 0.0345(6) Uani 1 1 d . . . . .
C8 C 0.3434(4) 0.51307(18) 0.63912(17) 0.0262(5) Uani 1 1 d . . . . .
C7 C 0.2976(4) 0.60757(17) 0.62425(17) 0.0248(5) Uani 1 1 d . . . . .
C9 C 0.4026(6) 0.4546(2) 0.57911(18) 0.0383(7) Uani 1 1 d . . . . .
C12 C 0.0921(6) 0.7296(2) 0.9062(2) 0.0447(8) Uani 1 1 d . . . . .
H12 H 0.084506 0.687103 0.947099 0.054 Uiso 1 1 calc R U . . .
H2 H 0.330(7) 0.945(3) 0.363(3) 0.058(13) Uiso 1 1 d . . . . .
H3 H 0.227(7) 0.794(4) 0.289(3) 0.067(16) Uiso 1 1 d . . . . .
H1A H 0.459(6) 0.907(3) 0.559(2) 0.035(9) Uiso 1 1 d . . . . .
H1C H 0.288(7) 0.961(3) 0.549(3) 0.054(13) Uiso 1 1 d . . . . .
H1B H 0.447(8) 0.980(4) 0.500(3) 0.064(14) Uiso 1 1 d . . . . .
H10 H 0.441(6) 0.284(3) 0.693(3) 0.052(12) Uiso 1 1 d . . . . .
H11 H 0.358(7) 0.384(3) 0.788(3) 0.058(13) Uiso 1 1 d . . . . .
H9 H 0.404(5) 0.470(2) 0.525(2) 0.021(7) Uiso 1 1 d . . . . .
H13 H 0.022(6) 0.832(3) 0.981(2) 0.031(9) Uiso 1 1 d . . . . .
H17 H 0.168(6) 0.844(3) 0.621(2) 0.035(9) Uiso 1 1 d . . . . .
H14 H 0.099(6) 0.910(3) 0.759(3) 0.044(11) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N5 1.963(2) . ?
Cu1 N4 2.051(2) . ?
Cu1 N6 2.064(2) . ?
Cu1 Cl1 2.2495(8) . ?
Cu1 Cl2 2.3628(9) . ?
N1 C4 1.370(3) . ?
N1 C2 1.374(4) . ?
N1 C1 1.463(4) . ?
N2 C4 1.328(4) . ?
N2 C3 1.368(4) . ?
N5 C16 1.335(3) . ?
N5 C7 1.343(3) . ?
N7 C13 1.320(5) . ?
N7 C14 1.330(4) . ?
C17 C16 1.390(4) . ?
C17 C5 1.399(4) . ?
C17 H17 0.92(4) . ?
N3 C10 1.337(4) . ?
N3 C9 1.341(4) . ?
N4 C11 1.334(4) . ?
N4 C8 1.344(4) . ?
N6 C12 1.319(4) . ?
N6 C15 1.356(4) . ?
C4 C5 1.463(3) . ?
C5 C6 1.406(4) . ?
C14 C15 1.396(4) . ?
C14 H14 0.98(4) . ?
C16 C15 1.469(4) . ?
C2 C3 1.361(5) . ?
C2 H2 0.88(5) . ?
C10 C11 1.388(4) . ?
C10 H10 0.96(5) . ?
C1 H1A 0.97(4) . ?
C1 H1C 0.90(5) . ?
C1 H1B 0.84(6) . ?
C6 C7 1.385(4) . ?
C6 H6 0.9300 . ?
C3 H3 0.94(5) . ?
C13 C12 1.400(4) . ?
C13 H13 0.98(4) . ?
C11 H11 0.93(5) . ?
C8 C9 1.388(4) . ?
C8 C7 1.479(3) . ?
C9 H9 0.92(3) . ?
C12 H12 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
N5 Cu1 N4 79.20(9) . . ?
N5 Cu1 N6 78.79(10) . . ?
N4 Cu1 N6 157.23(10) . . ?
N5 Cu1 Cl1 144.18(8) . . ?
N4 Cu1 Cl1 94.99(8) . . ?
N6 Cu1 Cl1 99.46(8) . . ?
N5 Cu1 Cl2 105.48(7) . . ?
N4 Cu1 Cl2 97.91(8) . . ?
N6 Cu1 Cl2 93.48(8) . . ?
Cl1 Cu1 Cl2 110.33(3) . . ?
C4 N1 C2 106.0(2) . . ?
C4 N1 C1 129.4(3) . . ?
C2 N1 C1 124.4(3) . . ?
C4 N2 C3 104.7(2) . . ?
C16 N5 C7 121.3(2) . . ?
C16 N5 Cu1 119.47(18) . . ?
C7 N5 Cu1 119.24(18) . . ?
C13 N7 C14 117.3(3) . . ?
C16 C17 C5 118.9(2) . . ?
C16 C17 H17 120(2) . . ?
C5 C17 H17 121(2) . . ?
C10 N3 C9 116.4(3) . . ?
C11 N4 C8 118.6(3) . . ?
C11 N4 Cu1 127.3(2) . . ?
C8 N4 Cu1 114.13(18) . . ?
C12 N6 C15 118.3(3) . . ?
C12 N6 Cu1 127.3(2) . . ?
C15 N6 Cu1 113.67(18) . . ?
N2 C4 N1 112.0(2) . . ?
N2 C4 C5 123.5(2) . . ?
N1 C4 C5 124.5(2) . . ?
C17 C5 C6 119.2(2) . . ?
C17 C5 C4 122.6(2) . . ?
C6 C5 C4 118.2(2) . . ?
N7 C14 C15 122.4(3) . . ?
N7 C14 H14 107(2) . . ?
C15 C14 H14 131(2) . . ?
N5 C16 C17 121.0(2) . . ?
N5 C16 C15 112.7(2) . . ?
C17 C16 C15 126.4(2) . . ?
C3 C2 N1 106.4(3) . . ?
C3 C2 H2 139(3) . . ?
N1 C2 H2 115(3) . . ?
N6 C15 C14 119.3(3) . . ?
N6 C15 C16 114.9(2) . . ?
C14 C15 C16 125.7(3) . . ?
N3 C10 C11 122.9(3) . . ?
N3 C10 H10 125(3) . . ?
C11 C10 H10 112(3) . . ?
N1 C1 H1A 110(2) . . ?
N1 C1 H1C 111(3) . . ?
H1A C1 H1C 104(4) . . ?
N1 C1 H1B 115(3) . . ?
H1A C1 H1B 108(4) . . ?
H1C C1 H1B 109(5) . . ?
C7 C6 C5 118.5(2) . . ?
C7 C6 H6 120.8 . . ?
C5 C6 H6 120.8 . . ?
C2 C3 N2 110.9(3) . . ?
C2 C3 H3 135(4) . . ?
N2 C3 H3 114(4) . . ?
N7 C13 C12 121.6(3) . . ?
N7 C13 H13 122(2) . . ?
C12 C13 H13 116(2) . . ?
N4 C11 C10 119.8(3) . . ?
N4 C11 H11 117(3) . . ?
C10 C11 H11 123(3) . . ?
N4 C8 C9 120.6(3) . . ?
N4 C8 C7 115.5(2) . . ?
C9 C8 C7 124.0(3) . . ?
N5 C7 C6 121.2(2) . . ?
N5 C7 C8 111.9(2) . . ?
C6 C7 C8 126.8(2) . . ?
N3 C9 C8 121.8(3) . . ?
N3 C9 H9 115(2) . . ?
C8 C9 H9 122(2) . . ?
N6 C12 C13 121.0(3) . . ?
N6 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?

_refine_diff_density_max         0.644
_refine_diff_density_min         -0.850
_refine_diff_density_rms         0.222



####################################################################### 
# 
# 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_SMSP224M_a
_database_code_depnum_ccdc_archive 'CCDC 2107293'
loop_
_audit_author_name
_audit_author_address
'Samit Pramanik'
;Jadavpur University
India
;
_audit_update_record             
;
2021-09-03 deposited with the CCDC.	2022-01-13 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         'C17 H13 Cl Cu N8 O3'
_chemical_formula_sum            'C17 H13 Cl Cu N8 O3'
_chemical_formula_weight         476.35

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'
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'
O O 0.0106 0.0060 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   6.9172(9)
_cell_length_b                   15.1342(19)
_cell_length_c                   17.174(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1797.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    3987
_cell_measurement_theta_min      1.794
_cell_measurement_theta_max      27.173

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.760
_exptl_crystal_F_000             964.0
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    1.405
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.803
_exptl_absorpt_correction_T_max  0.894
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD area-detector'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            54241
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_av_R_equivalents  0.0599
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.794
_diffrn_reflns_theta_max         27.173
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3979
_reflns_number_gt                3753
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.738
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    0.998

_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       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'APEX2(Bruker,2007)and SAINT (Bruker,2007)'
_computing_data_reduction        'SAINT(Bruker,2007)and XPREP(Bruker,2007)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    
;    
ORTEP-3 for Windows (Farrugia, 1997), DIAMOND (Brandenburg,
1999) and Mercury (Macrae et al., 2006)
;
_computing_publication_material  'PLATON (Spek, 2009)'
_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)+(0.1000P)²+0.8005P] 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_abs_structure_details 
;
 Flack x determined using 1528 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.000
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3979
_refine_ls_number_parameters     272
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0348
_refine_ls_wR_factor_ref         0.1122
_refine_ls_wR_factor_gt          0.1067
_refine_ls_goodness_of_fit_ref   0.883
_refine_ls_restrained_S_all      0.883
_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 0.80042(8) 0.58029(3) 0.18961(3) 0.03341(16) Uani 1 1 d . . . . .
Cl1 Cl 0.8802(2) 0.49638(8) 0.09065(6) 0.0462(3) Uani 1 1 d . . . . .
N5 N 0.7713(5) 0.6489(2) 0.28413(19) 0.0284(6) Uani 1 1 d . . . . .
N6 N 0.8285(5) 0.7056(2) 0.1459(2) 0.0322(7) Uani 1 1 d . . . . .
N1 N 0.7075(5) 0.8747(2) 0.5108(2) 0.0328(7) Uani 1 1 d . . . . .
N4 N 0.7526(5) 0.4816(2) 0.2674(2) 0.0324(7) Uani 1 1 d . . . . .
N2 N 0.7964(6) 0.7460(2) 0.5617(2) 0.0366(7) Uani 1 1 d . . . . .
N8 N 0.3160(5) 0.5831(2) 0.1975(2) 0.0383(7) Uani 1 1 d . . . . .
C7 C 0.7441(5) 0.6066(2) 0.3515(2) 0.0288(8) Uani 1 1 d . . . . .
O1 O 0.4558(7) 0.6175(3) 0.1612(3) 0.0697(13) Uani 1 1 d . . . . .
C4 C 0.7536(5) 0.7878(3) 0.4967(2) 0.0304(8) Uani 1 1 d . . . . .
C16 C 0.7937(6) 0.7365(2) 0.2815(2) 0.0305(7) Uani 1 1 d . . . . .
C15 C 0.8198(5) 0.7690(3) 0.2005(2) 0.0304(7) Uani 1 1 d . . . . .
N3 N 0.6463(8) 0.3656(3) 0.3848(3) 0.0516(11) Uani 1 1 d . . . . .
C8 C 0.7213(6) 0.5104(3) 0.3403(2) 0.0317(8) Uani 1 1 d . . . . .
N7 N 0.8566(8) 0.8827(3) 0.1054(3) 0.0512(11) Uani 1 1 d . . . . .
O2 O 0.1668(6) 0.6242(4) 0.2090(4) 0.089(2) Uani 1 1 d . . . . .
C10 C 0.6771(8) 0.3380(3) 0.3131(3) 0.0455(11) Uani 1 1 d . . . . .
H10 H 0.663750 0.278123 0.302049 0.055 Uiso 1 1 calc R U . . .
C12 C 0.8510(8) 0.7290(3) 0.0718(3) 0.0419(10) Uani 1 1 d . . . . .
H12 H 0.856962 0.685959 0.033176 0.050 Uiso 1 1 calc R U . . .
C17 C 0.7867(7) 0.7872(3) 0.3494(2) 0.0336(8) Uani 1 1 d . . . . .
H17 H 0.800384 0.848312 0.347383 0.040 Uiso 1 1 calc R U . . .
C6 C 0.7372(6) 0.6517(3) 0.4211(2) 0.0307(8) Uani 1 1 d . . . . .
H6 H 0.718554 0.621661 0.467772 0.037 Uiso 1 1 calc R U . . .
O3 O 0.3356(9) 0.5102(3) 0.2242(3) 0.0863(17) Uani 1 1 d . . . . .
C14 C 0.8324(7) 0.8576(3) 0.1791(3) 0.0432(10) Uani 1 1 d . . . . .
H14 H 0.823564 0.900726 0.217524 0.052 Uiso 1 1 calc R U . . .
C3 C 0.7786(8) 0.8071(3) 0.6193(3) 0.0424(10) Uani 1 1 d . . . . .
H3 H 0.801968 0.796442 0.671808 0.051 Uiso 1 1 calc R U . . .
C5 C 0.7589(5) 0.7444(3) 0.4201(2) 0.0301(8) Uani 1 1 d . . . . .
C2 C 0.7219(7) 0.8858(3) 0.5891(3) 0.0384(9) Uani 1 1 d . . . . .
H2 H 0.697496 0.937445 0.616741 0.046 Uiso 1 1 calc R U . . .
C13 C 0.8657(9) 0.8180(4) 0.0520(3) 0.0496(12) Uani 1 1 d . . . . .
H13 H 0.882435 0.833154 -0.000010 0.060 Uiso 1 1 calc R U . . .
C1 C 0.6271(8) 0.9400(3) 0.4579(3) 0.0433(10) Uani 1 1 d . . . . .
H1A H 0.566507 0.986221 0.487440 0.065 Uiso 1 1 calc R U . . .
H1C H 0.533015 0.912415 0.424827 0.065 Uiso 1 1 calc R U . . .
H1B H 0.728743 0.964595 0.426616 0.065 Uiso 1 1 calc R U . . .
C9 C 0.6667(9) 0.4519(3) 0.3984(3) 0.0473(12) Uani 1 1 d . . . . .
H9 H 0.643609 0.473421 0.448265 0.057 Uiso 1 1 calc R U . . .
C11 C 0.7294(8) 0.3957(3) 0.2533(3) 0.0401(10) Uani 1 1 d . . . . .
H11 H 0.748083 0.374019 0.203178 0.048 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N5 1.937(3) . ?
Cu1 N4 2.030(3) . ?
Cu1 N6 2.048(4) . ?
Cu1 Cl1 2.1921(12) . ?
N5 C7 1.335(5) . ?
N5 C16 1.337(5) . ?
N6 C12 1.331(6) . ?
N6 C15 1.343(5) . ?
N1 C2 1.360(6) . ?
N1 C4 1.375(5) . ?
N1 C1 1.453(6) . ?
N4 C11 1.332(5) . ?
N4 C8 1.343(5) . ?
N2 C4 1.316(6) . ?
N2 C3 1.359(5) . ?
N8 O3 1.201(6) . ?
N8 O2 1.221(6) . ?
N8 O1 1.263(6) . ?
C7 C6 1.377(5) . ?
C7 C8 1.478(5) . ?
C4 C5 1.471(5) . ?
C16 C17 1.396(6) . ?
C16 C15 1.487(5) . ?
C15 C14 1.393(6) . ?
N3 C10 1.317(7) . ?
N3 C9 1.334(6) . ?
C8 C9 1.386(6) . ?
N7 C14 1.331(7) . ?
N7 C13 1.342(7) . ?
C10 C11 1.397(7) . ?
C10 H10 0.9300 . ?
C12 C13 1.392(7) . ?
C12 H12 0.9300 . ?
C17 C5 1.389(6) . ?
C17 H17 0.9300 . ?
C6 C5 1.411(6) . ?
C6 H6 0.9300 . ?
C14 H14 0.9300 . ?
C3 C2 1.357(7) . ?
C3 H3 0.9300 . ?
C2 H2 0.9300 . ?
C13 H13 0.9300 . ?
C1 H1A 0.9600 . ?
C1 H1C 0.9600 . ?
C1 H1B 0.9600 . ?
C9 H9 0.9300 . ?
C11 H11 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
N5 Cu1 N4 79.97(14) . . ?
N5 Cu1 N6 79.67(14) . . ?
N4 Cu1 N6 159.56(14) . . ?
N5 Cu1 Cl1 170.47(11) . . ?
N4 Cu1 Cl1 97.18(10) . . ?
N6 Cu1 Cl1 103.21(11) . . ?
C7 N5 C16 121.3(3) . . ?
C7 N5 Cu1 119.0(3) . . ?
C16 N5 Cu1 119.5(3) . . ?
C12 N6 C15 118.8(4) . . ?
C12 N6 Cu1 127.4(3) . . ?
C15 N6 Cu1 113.7(3) . . ?
C2 N1 C4 106.0(4) . . ?
C2 N1 C1 124.2(4) . . ?
C4 N1 C1 129.1(4) . . ?
C11 N4 C8 117.8(4) . . ?
C11 N4 Cu1 128.1(3) . . ?
C8 N4 Cu1 113.7(3) . . ?
C4 N2 C3 105.7(4) . . ?
O3 N8 O2 120.1(6) . . ?
O3 N8 O1 118.7(5) . . ?
O2 N8 O1 121.0(5) . . ?
N5 C7 C6 121.4(4) . . ?
N5 C7 C8 112.0(3) . . ?
C6 C7 C8 126.7(4) . . ?
N2 C4 N1 111.2(4) . . ?
N2 C4 C5 122.6(3) . . ?
N1 C4 C5 126.2(4) . . ?
N5 C16 C17 120.9(4) . . ?
N5 C16 C15 111.9(3) . . ?
C17 C16 C15 127.2(4) . . ?
N6 C15 C14 120.1(4) . . ?
N6 C15 C16 115.0(3) . . ?
C14 C15 C16 125.0(4) . . ?
C10 N3 C9 117.3(4) . . ?
N4 C8 C9 120.6(4) . . ?
N4 C8 C7 115.0(3) . . ?
C9 C8 C7 124.4(4) . . ?
C14 N7 C13 116.6(4) . . ?
N3 C10 C11 122.0(4) . . ?
N3 C10 H10 119.0 . . ?
C11 C10 H10 119.0 . . ?
N6 C12 C13 119.9(4) . . ?
N6 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C5 C17 C16 118.5(4) . . ?
C5 C17 H17 120.7 . . ?
C16 C17 H17 120.7 . . ?
C7 C6 C5 118.5(4) . . ?
C7 C6 H6 120.7 . . ?
C5 C6 H6 120.7 . . ?
N7 C14 C15 122.2(4) . . ?
N7 C14 H14 118.9 . . ?
C15 C14 H14 118.9 . . ?
C2 C3 N2 110.2(4) . . ?
C2 C3 H3 124.9 . . ?
N2 C3 H3 124.9 . . ?
C17 C5 C6 119.3(4) . . ?
C17 C5 C4 125.2(4) . . ?
C6 C5 C4 115.5(4) . . ?
C3 C2 N1 106.9(4) . . ?
C3 C2 H2 126.5 . . ?
N1 C2 H2 126.6 . . ?
N7 C13 C12 122.4(5) . . ?
N7 C13 H13 118.8 . . ?
C12 C13 H13 118.8 . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1C C1 H1B 109.5 . . ?
N3 C9 C8 121.8(4) . . ?
N3 C9 H9 119.1 . . ?
C8 C9 H9 119.1 . . ?
N4 C11 C10 120.5(4) . . ?
N4 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?

_refine_diff_density_max         0.485
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.069



