# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2020

####################################################################### 
# 
# 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_SM_KD8_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1922811'
loop_
_audit_author_name
_audit_author_address
'kinsuk Das'
;Chandernagore College
India
;
_audit_update_record             
;
2019-06-13 deposited with the CCDC.	2020-03-30 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         'C15 H15 Cl N3 Ni O2, Cl'
_chemical_formula_sum            'C15 H15 Cl2 N3 Ni O2'
_chemical_formula_weight         398.89

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'
Ni Ni 0.3393 1.1124 '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      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                   12.485(6)
_cell_length_b                   9.687(4)
_cell_length_c                   14.318(6)
_cell_angle_alpha                90
_cell_angle_beta                 105.290(15)
_cell_angle_gamma                90
_cell_volume                     1670.4(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2655
_cell_measurement_theta_min      2.87
_cell_measurement_theta_max      25.88

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.586
_exptl_crystal_F_000             816
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.07
_exptl_absorpt_coefficient_mu    1.492
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.55
_exptl_absorpt_correction_T_max  0.84
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(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            24244
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.568
_diffrn_reflns_theta_max         27.139
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3686
_reflns_number_gt                3249
_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       '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+0.6725P] 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_number_reflns         3686
_refine_ls_number_parameters     224
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0273
_refine_ls_wR_factor_ref         0.1204
_refine_ls_wR_factor_gt          0.0934
_refine_ls_goodness_of_fit_ref   0.893
_refine_ls_restrained_S_all      0.893
_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
Ni1 Ni 0.67230(2) 0.15865(3) 0.45543(2) 0.03112(13) Uani 1 1 d . . . . .
Cl1 Cl 0.60341(5) 0.14964(6) 0.59576(4) 0.04040(16) Uani 1 1 d . . . . .
Cl2 Cl 0.86944(6) 0.38229(8) 0.28395(5) 0.0594(2) Uani 1 1 d . . . . .
O2 O 0.63518(14) -0.04669(16) 0.42854(13) 0.0391(3) Uani 1 1 d . . . . .
O1 O 0.7285(2) 0.1475(2) 0.32992(16) 0.0590(6) Uani 1 1 d . . . . .
N1 N 0.52753(16) 0.2637(2) 0.38063(13) 0.0416(4) Uani 1 1 d . . . . .
N2 N 0.72101(18) 0.35393(18) 0.47619(15) 0.0392(4) Uani 1 1 d . . . . .
N3 N 0.83591(15) 0.1351(2) 0.53833(14) 0.0396(4) Uani 1 1 d . . . . .
C1 C 0.4298(2) 0.2083(3) 0.33528(19) 0.0530(6) Uani 1 1 d . . . . .
H1 H 0.423532 0.112702 0.330998 0.064 Uiso 1 1 calc R U . . .
C5 C 0.5368(2) 0.4016(3) 0.38727(17) 0.0455(5) Uani 1 1 d . . . . .
C6 C 0.6482(2) 0.4532(2) 0.43804(18) 0.0477(6) Uani 1 1 d . . . . .
C3 C 0.3466(3) 0.4273(4) 0.3021(2) 0.0714(9) Uani 1 1 d . . . . .
H3 H 0.285217 0.482589 0.275603 0.086 Uiso 1 1 calc R U . . .
C2 C 0.3374(3) 0.2882(4) 0.2944(2) 0.0680(8) Uani 1 1 d . . . . .
H2 H 0.270478 0.247288 0.262323 0.082 Uiso 1 1 calc R U . . .
C4 C 0.4458(3) 0.4873(3) 0.3487(2) 0.0631(8) Uani 1 1 d . . . . .
H4 H 0.452437 0.582700 0.354463 0.076 Uiso 1 1 calc R U . . .
C15 C 0.8878(2) 0.0180(3) 0.56919(19) 0.0509(6) Uani 1 1 d . . . . .
H11 H 0.849233 -0.064666 0.553824 0.061 Uiso 1 1 calc R U . . .
C11 C 0.89064(19) 0.2566(3) 0.56160(17) 0.0458(6) Uani 1 1 d . . . . .
C13 C 1.0538(2) 0.1359(4) 0.6460(2) 0.0702(9) Uani 1 1 d . . . . .
H9 H 1.127820 0.135807 0.681620 0.084 Uiso 1 1 calc R U . . .
C10 C 0.8252(2) 0.3808(3) 0.52632(19) 0.0480(6) Uani 1 1 d . . . . .
C7 C 0.6800(3) 0.5904(3) 0.4487(3) 0.0739(10) Uani 1 1 d . . . . .
H5 H 0.630470 0.660577 0.422050 0.089 Uiso 1 1 calc R U . . .
C14 C 0.9978(2) 0.0140(4) 0.6237(2) 0.0652(8) Uani 1 1 d . . . . .
H10 H 1.032434 -0.069674 0.644550 0.078 Uiso 1 1 calc R U . . .
C8 C 0.7862(4) 0.6195(3) 0.4997(3) 0.0887(12) Uani 1 1 d . . . . .
H6 H 0.809067 0.711077 0.507160 0.106 Uiso 1 1 calc R U . . .
C12 C 1.0009(2) 0.2585(4) 0.6159(2) 0.0649(9) Uani 1 1 d . . . . .
H8 H 1.038238 0.341871 0.631687 0.078 Uiso 1 1 calc R U . . .
C9 C 0.8608(3) 0.5171(4) 0.5406(3) 0.0740(10) Uani 1 1 d . . . . .
H7 H 0.932386 0.538561 0.576516 0.089 Uiso 1 1 calc R U . . .
H12 H 0.765(3) 0.203(4) 0.314(2) 0.054(9) Uiso 1 1 d . . . . .
H14 H 0.631(3) -0.069(3) 0.375(2) 0.052(9) Uiso 1 1 d . . . . .
H15 H 0.573(3) -0.072(4) 0.432(2) 0.069(10) Uiso 1 1 d . . . . .
H13 H 0.711(3) 0.098(4) 0.291(2) 0.057(10) 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
Ni1 N2 1.9854(19) . ?
Ni1 O2 2.0557(18) . ?
Ni1 N3 2.087(2) . ?
Ni1 O1 2.097(2) . ?
Ni1 N1 2.105(2) . ?
Ni1 Cl1 2.3865(11) . ?
O2 H14 0.78(3) . ?
O2 H15 0.83(4) . ?
O1 H12 0.78(3) . ?
O1 H13 0.73(3) . ?
N1 C1 1.335(3) . ?
N1 C5 1.342(3) . ?
N2 C10 1.335(3) . ?
N2 C6 1.337(3) . ?
N3 C15 1.323(4) . ?
N3 C11 1.358(3) . ?
C1 C2 1.384(4) . ?
C1 H1 0.9300 . ?
C5 C4 1.397(4) . ?
C5 C6 1.477(4) . ?
C6 C7 1.384(4) . ?
C3 C2 1.354(5) . ?
C3 C4 1.371(5) . ?
C3 H3 0.9300 . ?
C2 H2 0.9300 . ?
C4 H4 0.9300 . ?
C15 C14 1.390(4) . ?
C15 H11 0.9300 . ?
C11 C12 1.391(4) . ?
C11 C10 1.467(4) . ?
C13 C14 1.367(5) . ?
C13 C12 1.372(5) . ?
C13 H9 0.9300 . ?
C10 C9 1.391(4) . ?
C7 C8 1.364(6) . ?
C7 H5 0.9300 . ?
C14 H10 0.9300 . ?
C8 C9 1.380(6) . ?
C8 H6 0.9300 . ?
C12 H8 0.9300 . ?
C9 H7 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
N2 Ni1 O2 174.33(8) . . ?
N2 Ni1 N3 78.69(9) . . ?
O2 Ni1 N3 98.01(8) . . ?
N2 Ni1 O1 91.07(8) . . ?
O2 Ni1 O1 84.25(8) . . ?
N3 Ni1 O1 89.04(9) . . ?
N2 Ni1 N1 78.65(9) . . ?
O2 Ni1 N1 104.59(8) . . ?
N3 Ni1 N1 157.34(9) . . ?
O1 Ni1 N1 91.45(9) . . ?
N2 Ni1 Cl1 94.18(6) . . ?
O2 Ni1 Cl1 90.51(5) . . ?
N3 Ni1 Cl1 91.90(6) . . ?
O1 Ni1 Cl1 174.75(6) . . ?
N1 Ni1 Cl1 89.67(6) . . ?
Ni1 O2 H14 114(2) . . ?
Ni1 O2 H15 116(2) . . ?
H14 O2 H15 99(3) . . ?
Ni1 O1 H12 125(2) . . ?
Ni1 O1 H13 126(3) . . ?
H12 O1 H13 108(4) . . ?
C1 N1 C5 119.0(2) . . ?
C1 N1 Ni1 127.24(18) . . ?
C5 N1 Ni1 113.54(16) . . ?
C10 N2 C6 122.7(2) . . ?
C10 N2 Ni1 118.85(18) . . ?
C6 N2 Ni1 118.43(18) . . ?
C15 N3 C11 119.4(2) . . ?
C15 N3 Ni1 127.09(17) . . ?
C11 N3 Ni1 113.49(17) . . ?
N1 C1 C2 122.2(3) . . ?
N1 C1 H1 118.9 . . ?
C2 C1 H1 118.9 . . ?
N1 C5 C4 121.2(3) . . ?
N1 C5 C6 115.1(2) . . ?
C4 C5 C6 123.7(3) . . ?
N2 C6 C7 120.1(3) . . ?
N2 C6 C5 114.1(2) . . ?
C7 C6 C5 125.8(3) . . ?
C2 C3 C4 120.5(3) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C3 C2 C1 118.6(3) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C3 C4 C5 118.5(3) . . ?
C3 C4 H4 120.8 . . ?
C5 C4 H4 120.8 . . ?
N3 C15 C14 122.4(3) . . ?
N3 C15 H11 118.8 . . ?
C14 C15 H11 118.8 . . ?
N3 C11 C12 120.6(3) . . ?
N3 C11 C10 115.3(2) . . ?
C12 C11 C10 124.1(3) . . ?
C14 C13 C12 120.0(3) . . ?
C14 C13 H9 120.0 . . ?
C12 C13 H9 120.0 . . ?
N2 C10 C9 119.5(3) . . ?
N2 C10 C11 113.6(2) . . ?
C9 C10 C11 126.9(3) . . ?
C8 C7 C6 117.8(3) . . ?
C8 C7 H5 121.1 . . ?
C6 C7 H5 121.1 . . ?
C13 C14 C15 118.4(3) . . ?
C13 C14 H10 120.8 . . ?
C15 C14 H10 120.8 . . ?
C7 C8 C9 122.1(3) . . ?
C7 C8 H6 119.0 . . ?
C9 C8 H6 119.0 . . ?
C13 C12 C11 119.2(3) . . ?
C13 C12 H8 120.4 . . ?
C11 C12 H8 120.4 . . ?
C8 C9 C10 117.8(3) . . ?
C8 C9 H7 121.1 . . ?
C10 C9 H7 121.1 . . ?

_refine_diff_density_max         0.828
_refine_diff_density_min         -1.272
_refine_diff_density_rms         0.391

####################################################################### 
# 
# 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_SMSP13_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1922812'
loop_
_audit_author_name
_audit_author_address
'kinsuk Das'
;Chandernagore College
India
;
_audit_update_record             
;
2019-06-13 deposited with the CCDC.	2020-03-30 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         'C15 H11 Cl2 Cu N3'
_chemical_formula_sum            'C15 H11 Cl2 Cu N3'
_chemical_formula_weight         367.72

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.6709(10)
_cell_length_b                   8.2581(7)
_cell_length_c                   16.0905(16)
_cell_angle_alpha                90
_cell_angle_beta                 94.686(3)
_cell_angle_gamma                90
_cell_volume                     1413.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    2560
_cell_measurement_theta_min      1.5
_cell_measurement_theta_max      26.0

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.728
_exptl_crystal_F_000             740
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    1.917
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.53
_exptl_absorpt_correction_T_max  0.91
_exptl_absorpt_process_details   SADABS
_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            20311
_diffrn_reflns_av_unetI/netI     0.0197
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.915
_diffrn_reflns_theta_max         27.218
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3130
_reflns_number_gt                2886
_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       '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+0.1636P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3130
_refine_ls_number_parameters     234
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0318
_refine_ls_R_factor_gt           0.0240
_refine_ls_wR_factor_ref         0.1103
_refine_ls_wR_factor_gt          0.0884
_refine_ls_goodness_of_fit_ref   0.938
_refine_ls_restrained_S_all      0.938
_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 0.29310(2) 0.43283(3) 0.39028(2) 0.02828(13) Uani 1 1 d . . . . .
Cl1 Cl 0.16384(5) 0.18542(6) 0.37147(3) 0.03601(15) Uani 1 1 d . . . . .
Cl2 Cl 0.36426(6) 0.47652(8) 0.26440(3) 0.04530(17) Uani 1 1 d . . . . .
N3 N 0.44342(16) 0.3073(2) 0.44663(11) 0.0305(3) Uani 1 1 d . . . . .
N1 N 0.15295(16) 0.6042(2) 0.38164(10) 0.0295(3) Uani 1 1 d . . . . .
N2 N 0.27118(15) 0.4719(2) 0.50845(10) 0.0267(3) Uani 1 1 d . . . . .
C11 C 0.44515(18) 0.2988(2) 0.53044(13) 0.0304(4) Uani 1 1 d . . . . .
C13 C 0.6253(2) 0.1263(3) 0.53684(18) 0.0430(5) Uani 1 1 d . . . . .
C14 C 0.6220(2) 0.1343(3) 0.45130(17) 0.0422(5) Uani 1 1 d . . . . .
C15 C 0.53009(19) 0.2259(3) 0.40763(15) 0.0368(5) Uani 1 1 d . . . . .
C6 C 0.17804(19) 0.5679(2) 0.52863(13) 0.0277(4) Uani 1 1 d . . . . .
C10 C 0.34410(19) 0.3926(2) 0.56642(12) 0.0291(4) Uani 1 1 d . . . . .
C12 C 0.5353(2) 0.2101(3) 0.57762(16) 0.0372(5) Uani 1 1 d . . . . .
C1 C 0.0990(2) 0.6722(3) 0.31203(14) 0.0370(5) Uani 1 1 d . . . . .
C8 C 0.2243(2) 0.5017(3) 0.67152(13) 0.0396(5) Uani 1 1 d . . . . .
C9 C 0.3229(2) 0.4048(3) 0.65009(14) 0.0370(5) Uani 1 1 d . . . . .
C2 C 0.0051(2) 0.7861(3) 0.31300(15) 0.0431(5) Uani 1 1 d . . . . .
C7 C 0.1513(2) 0.5868(3) 0.61159(14) 0.0350(5) Uani 1 1 d . . . . .
C5 C 0.11237(17) 0.6488(2) 0.45560(12) 0.0285(4) Uani 1 1 d . . . . .
C4 C 0.0190(2) 0.7636(3) 0.46104(15) 0.0366(4) Uani 1 1 d . . . . .
C3 C -0.0345(2) 0.8327(3) 0.38882(17) 0.0437(5) Uani 1 1 d . . . . .
H6 H 0.204(2) 0.511(3) 0.7218(18) 0.038(6) Uiso 1 1 d . . . . .
H3 H -0.094(3) 0.901(4) 0.389(2) 0.054(8) Uiso 1 1 d . . . . .
H2 H -0.032(3) 0.835(4) 0.262(2) 0.057(9) Uiso 1 1 d . . . . .
H4 H -0.009(2) 0.792(3) 0.5091(19) 0.041(7) Uiso 1 1 d . . . . .
H1 H 0.131(2) 0.643(4) 0.2641(19) 0.042(7) Uiso 1 1 d . . . . .
H5 H 0.088(3) 0.653(4) 0.6266(19) 0.048(8) Uiso 1 1 d . . . . .
H7 H 0.368(3) 0.349(3) 0.6871(19) 0.042(7) Uiso 1 1 d . . . . .
H10 H 0.675(3) 0.082(3) 0.4247(17) 0.034(7) Uiso 1 1 d . . . . .
H9 H 0.679(3) 0.068(3) 0.5623(19) 0.039(7) Uiso 1 1 d . . . . .
H8 H 0.532(2) 0.211(3) 0.6297(19) 0.040(7) Uiso 1 1 d . . . . .
H11 H 0.531(2) 0.242(3) 0.3521(19) 0.038(6) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N2 1.9614(16) . ?
Cu1 N1 2.0552(18) . ?
Cu1 N3 2.0572(17) . ?
Cu1 Cl2 2.2496(6) . ?
Cu1 Cl1 2.4699(6) . ?
N3 C15 1.340(3) . ?
N3 C11 1.349(3) . ?
N1 C1 1.340(3) . ?
N1 C5 1.350(2) . ?
N2 C6 1.332(3) . ?
N2 C10 1.336(3) . ?
C11 C12 1.386(3) . ?
C11 C10 1.483(3) . ?
C13 C14 1.376(4) . ?
C13 C12 1.391(3) . ?
C13 H9 0.83(3) . ?
C14 C15 1.384(3) . ?
C14 H10 0.85(3) . ?
C15 H11 0.91(3) . ?
C6 C7 1.396(3) . ?
C6 C5 1.477(3) . ?
C10 C9 1.387(3) . ?
C12 H8 0.84(3) . ?
C1 C2 1.376(3) . ?
C1 H1 0.90(3) . ?
C8 C7 1.381(3) . ?
C8 C9 1.387(3) . ?
C8 H6 0.86(3) . ?
C9 H7 0.87(3) . ?
C2 C3 1.378(4) . ?
C2 H2 0.97(3) . ?
C7 H5 0.91(3) . ?
C5 C4 1.384(3) . ?
C4 C3 1.376(4) . ?
C4 H4 0.88(3) . ?
C3 H3 0.85(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Cu1 N1 78.96(7) . . ?
N2 Cu1 N3 78.82(7) . . ?
N1 Cu1 N3 156.00(7) . . ?
N2 Cu1 Cl2 157.25(5) . . ?
N1 Cu1 Cl2 97.24(5) . . ?
N3 Cu1 Cl2 99.74(5) . . ?
N2 Cu1 Cl1 98.36(5) . . ?
N1 Cu1 Cl1 99.51(5) . . ?
N3 Cu1 Cl1 92.57(5) . . ?
Cl2 Cu1 Cl1 104.39(2) . . ?
C15 N3 C11 119.23(19) . . ?
C15 N3 Cu1 126.12(16) . . ?
C11 N3 Cu1 114.41(13) . . ?
C1 N1 C5 118.40(18) . . ?
C1 N1 Cu1 127.26(15) . . ?
C5 N1 Cu1 114.34(13) . . ?
C6 N2 C10 121.68(17) . . ?
C6 N2 Cu1 118.99(14) . . ?
C10 N2 Cu1 119.15(13) . . ?
N3 C11 C12 121.82(19) . . ?
N3 C11 C10 114.34(17) . . ?
C12 C11 C10 123.8(2) . . ?
C14 C13 C12 119.1(2) . . ?
C14 C13 H9 119(2) . . ?
C12 C13 H9 122(2) . . ?
C13 C14 C15 119.6(2) . . ?
C13 C14 H10 120.9(19) . . ?
C15 C14 H10 119.5(19) . . ?
N3 C15 C14 121.6(2) . . ?
N3 C15 H11 117.0(17) . . ?
C14 C15 H11 121.0(17) . . ?
N2 C6 C7 120.93(19) . . ?
N2 C6 C5 112.95(17) . . ?
C7 C6 C5 126.12(19) . . ?
N2 C10 C9 120.64(19) . . ?
N2 C10 C11 112.58(17) . . ?
C9 C10 C11 126.8(2) . . ?
C11 C12 C13 118.7(2) . . ?
C11 C12 H8 117.4(18) . . ?
C13 C12 H8 123.9(18) . . ?
N1 C1 C2 122.7(2) . . ?
N1 C1 H1 115.7(19) . . ?
C2 C1 H1 121.5(18) . . ?
C7 C8 C9 121.0(2) . . ?
C7 C8 H6 116.5(19) . . ?
C9 C8 H6 122.4(19) . . ?
C10 C9 C8 118.1(2) . . ?
C10 C9 H7 120.1(19) . . ?
C8 C9 H7 121.8(19) . . ?
C1 C2 C3 118.5(2) . . ?
C1 C2 H2 122(2) . . ?
C3 C2 H2 119.6(19) . . ?
C8 C7 C6 117.6(2) . . ?
C8 C7 H5 120.3(19) . . ?
C6 C7 H5 122.1(19) . . ?
N1 C5 C4 121.81(19) . . ?
N1 C5 C6 114.35(17) . . ?
C4 C5 C6 123.82(19) . . ?
C3 C4 C5 118.8(2) . . ?
C3 C4 H4 119.1(18) . . ?
C5 C4 H4 122.1(18) . . ?
C4 C3 C2 119.8(2) . . ?
C4 C3 H3 122(2) . . ?
C2 C3 H3 118(2) . . ?

_refine_diff_density_max         0.826
_refine_diff_density_min         -0.924
_refine_diff_density_rms         0.257

