# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2005016'
loop_
_audit_author_name
_audit_author_address
'Aurobinda Mohanty'
;Department of Chemistry, IIT Roorkee
India
;
_audit_update_record             
;
2020-05-21 deposited with the CCDC.	2020-09-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H30 Cl Cu N3 P'
_chemical_formula_sum            'C36 H30 Cl Cu N3 P'
_chemical_formula_weight         634.60

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      Hexagonal
_space_group_IT_number           144
_space_group_name_H-M_alt        'P 31'
_space_group_name_Hall           'P 31'

_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'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'

_cell_length_a                   10.2089(3)
_cell_length_b                   10.2089(3)
_cell_length_c                   26.3489(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     2378.21(19)
_cell_formula_units_Z            3
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1519
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      27.13

_exptl_crystal_description       SQUARE
_exptl_crystal_colour            GREEN
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_F_000             984
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.23
_exptl_absorpt_coefficient_mu    0.853
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.822
_exptl_absorpt_correction_T_max  0.822
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_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  'CCD area detector'
_diffrn_measurement_method       'phi omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28210
_diffrn_reflns_av_unetI/netI     0.0467
_diffrn_reflns_av_R_equivalents  0.0595
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.546
_diffrn_reflns_theta_max         23.839
_diffrn_reflns_theta_full        23.839
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4884
_reflns_number_gt                4586
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.999
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    0.996

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0277P)²+0.3709P] 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 2037 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.032(7)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4852
_refine_ls_number_parameters     380
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0336
_refine_ls_wR_factor_ref         0.0720
_refine_ls_wR_factor_gt          0.0710
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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 -0.27793(9) -0.44596(10) -0.06193(3) 0.0503(2) Uani 1 1 d . . . . .
P2 P -0.37962(19) -0.4924(2) -0.13765(6) 0.0433(4) Uani 1 1 d . . . . .
Cl3 Cl -0.06179(19) -0.4524(2) -0.04610(7) 0.0578(5) Uani 1 1 d . . . . .
N4 N -0.2592(6) -0.2605(7) -0.0237(2) 0.0527(14) Uani 1 1 d . . . . .
C62 C -0.3440(10) -0.1679(11) 0.0440(4) 0.078(3) Uani 1 1 d . . . . .
H62 H -0.410684 -0.187522 0.070810 0.094 Uiso 1 1 calc R U . . .
C89 C -0.5827(8) -0.5698(9) -0.1340(2) 0.0500(18) Uani 1 1 d . . . . .
C63 C -0.3553(8) -0.2875(9) 0.0142(3) 0.054(2) Uani 1 1 d . . . . .
C88 C -0.3572(7) -0.6210(7) -0.1801(2) 0.0386(14) Uani 1 1 d . . . . .
C60 C -0.1350(12) 0.0036(11) -0.0046(4) 0.086(3) Uani 1 1 d . . . . .
H60 H -0.057842 0.101611 -0.011274 0.103 Uiso 1 1 calc R U . . .
C86 C -0.3888(9) -0.7422(9) -0.2610(3) 0.0591(19) Uani 1 1 d . . . . .
H86 H -0.427184 -0.760679 -0.293882 0.071 Uiso 1 1 calc R U . . .
C84 C -0.2510(9) -0.7815(8) -0.1961(3) 0.059(2) Uani 1 1 d . . . . .
H84 H -0.197617 -0.827867 -0.184949 0.070 Uiso 1 1 calc R U . . .
C59 C -0.1522(9) -0.1175(9) -0.0324(3) 0.071(2) Uani 1 1 d . . . . .
H59 H -0.085246 -0.098861 -0.058992 0.085 Uiso 1 1 calc R U . . .
C85 C -0.3088(9) -0.8063(9) -0.2441(3) 0.0560(19) Uani 1 1 d . . . . .
H85 H -0.292685 -0.868829 -0.265741 0.067 Uiso 1 1 calc R U . . .
C83 C -0.2734(7) -0.6849(8) -0.1637(3) 0.0483(17) Uani 1 1 d . . . . .
H83 H -0.231776 -0.664156 -0.131259 0.058 Uiso 1 1 calc R U . . .
C92 C -0.6843(9) -0.7191(11) -0.1420(3) 0.078(3) Uani 1 1 d . . . . .
H92 H -0.651534 -0.783986 -0.153543 0.093 Uiso 1 1 calc R U . . .
C90 C -0.6380(10) -0.4795(11) -0.1156(4) 0.081(3) Uani 1 1 d . . . . .
H90 H -0.568826 -0.378399 -0.109030 0.097 Uiso 1 1 calc R U . . .
C93 C -0.8383(11) -0.7741(14) -0.1328(5) 0.115(4) Uani 1 1 d . . . . .
H93 H -0.907748 -0.875476 -0.138754 0.138 Uiso 1 1 calc R U . . .
C94 C -0.8886(12) -0.6782(19) -0.1148(4) 0.108(4) Uani 1 1 d . . . . .
H94 H -0.990750 -0.715196 -0.108423 0.130 Uiso 1 1 calc R U . . .
C91 C -0.7848(11) -0.5284(15) -0.1068(4) 0.091(3) Uani 1 1 d . . . . .
H91 H -0.815735 -0.462005 -0.095312 0.109 Uiso 1 1 calc R U . . .
C87 C -0.4135(7) -0.6482(8) -0.2288(3) 0.0481(17) Uani 1 1 d . . . . .
H87 H -0.468171 -0.603591 -0.240327 0.058 Uiso 1 1 calc R U . . .
C61 C -0.2381(12) -0.0280(11) 0.0338(4) 0.086(3) Uani 1 1 d . . . . .
H61 H -0.232986 0.051116 0.052859 0.103 Uiso 1 1 calc R U . . .
C81 C -0.3986(11) -0.2976(10) -0.2114(4) 0.076(2) Uani 1 1 d . . . . .
H81 H -0.503078 -0.360563 -0.211478 0.092 Uiso 1 1 calc R U . . .
C71 C -0.5674(9) -0.8143(8) -0.0255(3) 0.0570(18) Uani 1 1 d . . . . .
N5 N -0.4683(7) -0.4380(7) 0.0217(2) 0.0645(18) Uani 1 1 d . . . . .
C65 C -0.5972(8) -0.4740(9) 0.0539(3) 0.058(2) Uani 1 1 d . . . . .
N8 N -0.4579(6) -0.5485(7) -0.0055(2) 0.0493(14) Uani 1 1 d . . . . .
C82 C -0.3093(8) -0.3262(7) -0.1788(3) 0.0503(18) Uani 1 1 d . . . . .
C70 C -0.5677(8) -0.6863(9) -0.0005(3) 0.061(2) Uani 1 1 d . . . . .
H70 H -0.649852 -0.704764 0.019745 0.073 Uiso 1 1 calc R U . . .
C77 C -0.1540(9) -0.2300(9) -0.1795(3) 0.068(2) Uani 1 1 d . . . . .
H77 H -0.091181 -0.244273 -0.157440 0.081 Uiso 1 1 calc R U . . .
C76 C -0.4449(9) -0.8141(8) -0.0456(3) 0.059(2) Uani 1 1 d . . . . .
H76 H -0.350918 -0.726239 -0.044775 0.071 Uiso 1 1 calc R U . . .
C68 C -0.8475(10) -0.5535(11) 0.1122(4) 0.082(3) Uani 1 1 d . . . . .
H68 H -0.932117 -0.577847 0.131965 0.099 Uiso 1 1 calc R U . . .
C78 C -0.0948(13) -0.1116(12) -0.2143(5) 0.099(3) Uani 1 1 d . . . . .
H78 H 0.009545 -0.048186 -0.215303 0.119 Uiso 1 1 calc R U . . .
C75 C -0.4593(12) -0.9456(11) -0.0675(4) 0.086(3) Uani 1 1 d . . . . .
H75 H -0.374979 -0.946383 -0.080477 0.103 Uiso 1 1 calc R U . . .
C69 C -0.7266(14) -0.5487(11) 0.1335(4) 0.089(3) Uani 1 1 d . . . . .
H69 H -0.727398 -0.569370 0.167876 0.107 Uiso 1 1 calc R U . . .
C80 C -0.3305(16) -0.1727(14) -0.2445(5) 0.107(4) Uani 1 1 d . . . . .
H80 H -0.390614 -0.151090 -0.265458 0.129 Uiso 1 1 calc R U . . .
C79 C -0.1792(16) -0.0843(13) -0.2461(5) 0.102(4) Uani 1 1 d . . . . .
H79 H -0.134150 -0.004987 -0.269205 0.123 Uiso 1 1 calc R U . . .
C72 C -0.7083(10) -0.9484(10) -0.0275(4) 0.085(3) Uani 1 1 d . . . . .
H72 H -0.791943 -0.949630 -0.013032 0.102 Uiso 1 1 calc R U . . .
C67 C -0.8491(10) -0.5236(11) 0.0624(4) 0.085(3) Uani 1 1 d . . . . .
H67 H -0.935545 -0.530111 0.048090 0.103 Uiso 1 1 calc R U . . .
C64 C -0.5959(11) -0.5117(12) 0.1035(4) 0.081(3) Uani 1 1 d . . . . .
H64 H -0.512878 -0.513403 0.117284 0.097 Uiso 1 1 calc R U . . .
C66 C -0.7230(10) -0.4831(12) 0.0322(4) 0.087(3) Uani 1 1 d . . . . .
H66 H -0.724139 -0.462556 -0.002115 0.104 Uiso 1 1 calc R U . . .
C74 C -0.5979(15) -1.0720(10) -0.0697(4) 0.105(4) Uani 1 1 d . . . . .
H74 H -0.607408 -1.158620 -0.084854 0.126 Uiso 1 1 calc R U . . .
C73 C -0.7263(13) -1.0757(13) -0.0498(5) 0.117(4) Uani 1 1 d . . . . .
H73 H -0.820864 -1.162501 -0.051735 0.141 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 N4 2.067(6) . ?
Cu1 N8 2.182(6) . ?
Cu1 P2 2.1889(17) . ?
Cu1 Cl3 2.2787(19) . ?
P2 C89 1.815(7) . ?
P2 C88 1.824(6) . ?
P2 C82 1.830(7) . ?
N4 C63 1.328(9) . ?
N4 C59 1.335(10) . ?
C62 C61 1.319(12) . ?
C62 C63 1.408(11) . ?
C89 C92 1.365(11) . ?
C89 C90 1.387(11) . ?
C63 N5 1.399(10) . ?
C88 C87 1.377(9) . ?
C88 C83 1.379(9) . ?
C60 C59 1.370(11) . ?
C60 C61 1.377(14) . ?
C86 C85 1.353(11) . ?
C86 C87 1.395(11) . ?
C84 C85 1.365(10) . ?
C84 C83 1.407(10) . ?
C92 C93 1.401(14) . ?
C90 C91 1.342(12) . ?
C93 C94 1.396(17) . ?
C94 C91 1.373(16) . ?
C81 C82 1.388(11) . ?
C81 C80 1.408(14) . ?
C71 C76 1.357(10) . ?
C71 C72 1.406(12) . ?
C71 C70 1.465(11) . ?
N5 N8 1.384(8) . ?
N5 C65 1.450(9) . ?
C65 C64 1.364(12) . ?
C65 C66 1.365(11) . ?
N8 C70 1.295(9) . ?
C82 C77 1.386(10) . ?
C77 C78 1.391(13) . ?
C76 C75 1.400(11) . ?
C68 C69 1.335(14) . ?
C68 C67 1.349(13) . ?
C78 C79 1.328(16) . ?
C75 C74 1.358(14) . ?
C69 C64 1.430(13) . ?
C80 C79 1.345(17) . ?
C72 C73 1.351(15) . ?
C67 C66 1.389(12) . ?
C74 C73 1.395(15) . ?

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
N4 Cu1 N8 77.1(2) . . ?
N4 Cu1 P2 117.32(18) . . ?
N8 Cu1 P2 108.86(15) . . ?
N4 Cu1 Cl3 106.84(17) . . ?
N8 Cu1 Cl3 117.15(15) . . ?
P2 Cu1 Cl3 121.46(7) . . ?
C89 P2 C88 104.2(3) . . ?
C89 P2 C82 105.6(3) . . ?
C88 P2 C82 99.9(3) . . ?
C89 P2 Cu1 111.2(2) . . ?
C88 P2 Cu1 119.9(2) . . ?
C82 P2 Cu1 114.5(2) . . ?
C63 N4 C59 118.1(7) . . ?
C63 N4 Cu1 117.1(5) . . ?
C59 N4 Cu1 124.7(5) . . ?
C61 C62 C63 119.5(9) . . ?
C92 C89 C90 117.5(8) . . ?
C92 C89 P2 122.9(6) . . ?
C90 C89 P2 119.0(6) . . ?
N4 C63 N5 116.9(6) . . ?
N4 C63 C62 120.5(8) . . ?
N5 C63 C62 122.5(7) . . ?
C87 C88 C83 119.5(6) . . ?
C87 C88 P2 121.8(5) . . ?
C83 C88 P2 118.6(5) . . ?
C59 C60 C61 116.3(9) . . ?
C85 C86 C87 119.5(7) . . ?
C85 C84 C83 119.1(7) . . ?
N4 C59 C60 124.1(8) . . ?
C86 C85 C84 121.7(7) . . ?
C88 C83 C84 119.9(6) . . ?
C89 C92 C93 119.6(10) . . ?
C91 C90 C89 124.2(9) . . ?
C94 C93 C92 120.7(10) . . ?
C91 C94 C93 118.9(9) . . ?
C90 C91 C94 118.9(10) . . ?
C88 C87 C86 120.3(6) . . ?
C62 C61 C60 121.4(9) . . ?
C82 C81 C80 119.7(9) . . ?
C76 C71 C72 118.7(7) . . ?
C76 C71 C70 126.0(7) . . ?
C72 C71 C70 115.3(7) . . ?
N8 N5 C63 117.6(6) . . ?
N8 N5 C65 121.7(6) . . ?
C63 N5 C65 120.5(6) . . ?
C64 C65 C66 121.6(8) . . ?
C64 C65 N5 119.7(7) . . ?
C66 C65 N5 118.5(7) . . ?
C70 N8 N5 117.1(6) . . ?
C70 N8 Cu1 130.9(5) . . ?
N5 N8 Cu1 110.6(4) . . ?
C77 C82 C81 118.8(8) . . ?
C77 C82 P2 116.4(6) . . ?
C81 C82 P2 124.6(6) . . ?
N8 C70 C71 122.5(6) . . ?
C82 C77 C78 118.1(9) . . ?
C71 C76 C75 120.3(8) . . ?
C69 C68 C67 121.1(8) . . ?
C79 C78 C77 123.5(10) . . ?
C74 C75 C76 119.3(10) . . ?
C68 C69 C64 120.1(9) . . ?
C79 C80 C81 120.6(11) . . ?
C78 C79 C80 119.2(10) . . ?
C73 C72 C71 122.3(9) . . ?
C68 C67 C66 120.6(8) . . ?
C65 C64 C69 117.6(9) . . ?
C65 C66 C67 118.8(9) . . ?
C75 C74 C73 121.9(11) . . ?
C72 C73 C74 117.6(10) . . ?

_refine_diff_density_max         0.337
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.036

