#------------------------------------------------------------------------------
#$Date: 2022-05-05 22:46:44 +0200 (jue 05 de may de 2022) $
#$Revision: 275030 $
#$URL: svn://www.crystallography.net/cod/cif/7/06/14/7061403.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7061403
loop_
_publ_author_name
'Kumar, Sunil'
'Choudhary, Mukesh'
_publ_section_title
;
 Structure-based design and synthesis of copper(ii) complexes as antivirus
 drug candidates targeting SARS CoV-2 and HIV
;
_journal_issue                   15
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              7128
_journal_page_last               7143
_journal_paper_doi               10.1039/D2NJ00703G
_journal_volume                  46
_journal_year                    2022
_chemical_formula_sum            'C28 H20 Cl4 Cu N2 O4'
_chemical_formula_weight         653.80
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-01-21 deposited with the CCDC.	2022-03-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.863(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.4630(12)
_cell_length_b                   9.2765(10)
_cell_length_c                   12.6425(13)
_cell_measurement_reflns_used    9686
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      33.08
_cell_measurement_theta_min      2.80
_cell_volume                     1356.5(2)
_computing_cell_refinement       'APEX3/SAINT (Bruker, 2016)'
_computing_data_collection       'APEX3(Bruker, 2016)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2016)'
_computing_molecular_graphics
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
'Bruker axs kappa apex3 PHOTON II Diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0711
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            52736
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.995
_diffrn_reflns_theta_min         2.943
_diffrn_source                   'fine focus sealed tube'
_exptl_absorpt_coefficient_mu    1.238
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.565
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker 2016)'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.601
_exptl_crystal_description       block
_exptl_crystal_F_000             662
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.479
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     179
_refine_ls_number_reflns         3943
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.134
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0341
_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)+(0.0703P)²+0.4715P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1030
_refine_ls_wR_factor_ref         0.1234
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3300
_reflns_number_total             3943
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2nj00703g2.cif
_cod_data_source_block           shelx
_cod_depositor_comments
'Adding full bibliography for 7061403--7061404.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7061403
_shelx_shelxl_version_number     2018/3
_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.
;
_shelx_estimated_absorpt_t_min   0.723
_shelx_estimated_absorpt_t_max   0.918
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'
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 0.500000 0.500000 0.500000 0.02631(11) Uani 1 2 d S . P . .
Cl1 Cl 1.06218(4) 0.18781(7) 0.82472(5) 0.04838(16) Uani 1 1 d . . . . .
Cl2 Cl 0.87991(5) 0.63281(8) 0.54220(7) 0.0659(2) Uani 1 1 d . . . . .
C1 C 0.62510(16) 0.2721(2) 0.65815(17) 0.0334(4) Uani 1 1 d . . . . .
H1 H 0.625486 0.189400 0.702572 0.040 Uiso 1 1 calc R U . . .
C2 C 0.73662(15) 0.3262(2) 0.66696(16) 0.0303(4) Uani 1 1 d . . . . .
C3 C 0.74734(14) 0.44991(19) 0.60616(15) 0.0268(3) Uani 1 1 d . . . . .
C4 C 0.86250(17) 0.4858(2) 0.61729(18) 0.0329(4) Uani 1 1 d . . . . .
C5 C 0.95764(16) 0.4085(2) 0.68397(16) 0.0337(4) Uani 1 1 d . . . . .
H5 H 1.032928 0.436631 0.689817 0.040 Uiso 1 1 calc R U . . .
C6 C 0.94246(16) 0.2887(2) 0.74268(17) 0.0338(4) Uani 1 1 d . . . . .
C7 C 0.83417(17) 0.2471(2) 0.73506(18) 0.0369(4) Uani 1 1 d . . . . .
H7 H 0.825099 0.164938 0.775772 0.044 Uiso 1 1 calc R U . . .
C8 C 0.42994(15) 0.23548(19) 0.59922(16) 0.0287(3) Uani 1 1 d . . . . .
C9 C 0.38125(18) 0.2586(2) 0.68000(18) 0.0369(4) Uani 1 1 d . . . . .
H9 H 0.407562 0.335781 0.732805 0.044 Uiso 1 1 calc R U . . .
C10 C 0.29374(18) 0.1683(2) 0.68324(18) 0.0386(4) Uani 1 1 d . . . . .
H10 H 0.261083 0.182864 0.739364 0.046 Uiso 1 1 calc R U . . .
C11 C 0.25375(17) 0.0573(2) 0.60545(17) 0.0344(4) Uani 1 1 d . . . . .
C12 C 0.3008(2) 0.0356(2) 0.52302(19) 0.0393(4) Uani 1 1 d . . . . .
H12 H 0.272971 -0.039636 0.468679 0.047 Uiso 1 1 calc R U . . .
C13 C 0.38952(18) 0.1258(2) 0.52102(18) 0.0368(4) Uani 1 1 d . . . . .
H13 H 0.422437 0.111477 0.465067 0.044 Uiso 1 1 calc R U . . .
C14 C 0.1182(3) -0.1324(3) 0.5305(3) 0.0600(7) Uani 1 1 d . . . . .
H14A H 0.081718 -0.086067 0.455910 0.090 Uiso 1 1 calc R U . . .
H14B H 0.060103 -0.187427 0.548478 0.090 Uiso 1 1 calc R U . . .
H14C H 0.179392 -0.197482 0.528568 0.090 Uiso 1 1 calc R U . . .
N1 N 0.52538(13) 0.32301(16) 0.59716(13) 0.0287(3) Uani 1 1 d . . . . .
O1 O 0.66176(11) 0.52963(15) 0.54432(13) 0.0328(3) Uani 1 1 d . . . . .
O2 O 0.16684(17) -0.0249(2) 0.61539(16) 0.0493(4) Uani 1 1 d . . . . .
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'
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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
O1 Cu1 O1 180.0 . 3_666 ?
O1 Cu1 N1 91.71(6) . . ?
O1 Cu1 N1 88.29(6) 3_666 . ?
O1 Cu1 N1 88.29(6) . 3_666 ?
O1 Cu1 N1 91.71(6) 3_666 3_666 ?
N1 Cu1 N1 180.00(8) . 3_666 ?
N1 C1 C2 127.45(17) . . ?
N1 C1 H1 116.3 . . ?
C2 C1 H1 116.3 . . ?
C7 C2 C3 121.37(16) . . ?
C7 C2 C1 117.03(17) . . ?
C3 C2 C1 121.55(16) . . ?
O1 C3 C2 124.64(16) . . ?
O1 C3 C4 119.88(16) . . ?
C2 C3 C4 115.49(16) . . ?
C5 C4 C3 123.00(17) . . ?
C5 C4 Cl2 119.68(15) . . ?
C3 C4 Cl2 117.32(14) . . ?
C4 C5 C6 119.21(17) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C7 C6 C5 120.94(17) . . ?
C7 C6 Cl1 119.56(15) . . ?
C5 C6 Cl1 119.49(15) . . ?
C6 C7 C2 119.99(18) . . ?
C6 C7 H7 120.0 . . ?
C2 C7 H7 120.0 . . ?
C13 C8 C9 120.03(17) . . ?
C13 C8 N1 118.98(16) . . ?
C9 C8 N1 120.97(17) . . ?
C8 C9 C10 119.53(19) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C11 C10 C9 120.52(19) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
O2 C11 C10 115.98(18) . . ?
O2 C11 C12 123.96(19) . . ?
C10 C11 C12 120.06(17) . . ?
C11 C12 C13 119.11(19) . . ?
C11 C12 H12 120.4 . . ?
C13 C12 H12 120.4 . . ?
C8 C13 C12 120.73(18) . . ?
C8 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
O2 C14 H14A 109.5 . . ?
O2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C1 N1 C8 113.63(15) . . ?
C1 N1 Cu1 124.47(13) . . ?
C8 N1 Cu1 121.81(11) . . ?
C3 O1 Cu1 129.83(12) . . ?
C11 O2 C14 116.74(18) . . ?
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 O1 1.9007(13) . ?
Cu1 O1 1.9007(13) 3_666 ?
Cu1 N1 2.0037(15) . ?
Cu1 N1 2.0038(15) 3_666 ?
Cl1 C6 1.7395(19) . ?
Cl2 C4 1.7207(19) . ?
C1 N1 1.284(2) . ?
C1 C2 1.442(2) . ?
C1 H1 0.9500 . ?
C2 C7 1.406(3) . ?
C2 C3 1.415(2) . ?
C3 O1 1.294(2) . ?
C3 C4 1.428(2) . ?
C4 C5 1.374(3) . ?
C5 C6 1.387(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.372(3) . ?
C7 H7 0.9500 . ?
C8 C13 1.376(3) . ?
C8 C9 1.385(3) . ?
C8 N1 1.449(2) . ?
C9 C10 1.388(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.382(3) . ?
C10 H10 0.9500 . ?
C11 O2 1.368(2) . ?
C11 C12 1.388(3) . ?
C12 C13 1.394(3) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 O2 1.424(3) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C7 H7 O1 0.95 2.55 3.428(2) 153.8 2_646 yes
C14 H14B Cl2 0.98 2.77 3.731(2) 165.3 1_445 yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C7 -176.6(2) . . . . ?
N1 C1 C2 C3 0.9(3) . . . . ?
C7 C2 C3 O1 -178.20(19) . . . . ?
C1 C2 C3 O1 4.4(3) . . . . ?
C7 C2 C3 C4 1.2(3) . . . . ?
C1 C2 C3 C4 -176.18(18) . . . . ?
O1 C3 C4 C5 178.13(19) . . . . ?
C2 C3 C4 C5 -1.3(3) . . . . ?
O1 C3 C4 Cl2 -2.1(3) . . . . ?
C2 C3 C4 Cl2 178.44(15) . . . . ?
C3 C4 C5 C6 0.8(3) . . . . ?
Cl2 C4 C5 C6 -178.95(16) . . . . ?
C4 C5 C6 C7 -0.1(3) . . . . ?
C4 C5 C6 Cl1 178.54(16) . . . . ?
C5 C6 C7 C2 0.0(3) . . . . ?
Cl1 C6 C7 C2 -178.62(17) . . . . ?
C3 C2 C7 C6 -0.6(3) . . . . ?
C1 C2 C7 C6 176.9(2) . . . . ?
C13 C8 C9 C10 1.7(3) . . . . ?
N1 C8 C9 C10 -176.81(19) . . . . ?
C8 C9 C10 C11 -1.1(3) . . . . ?
C9 C10 C11 O2 -179.6(2) . . . . ?
C9 C10 C11 C12 -0.2(3) . . . . ?
O2 C11 C12 C13 -179.8(2) . . . . ?
C10 C11 C12 C13 0.9(3) . . . . ?
C9 C8 C13 C12 -1.0(3) . . . . ?
N1 C8 C13 C12 177.50(19) . . . . ?
C11 C12 C13 C8 -0.3(3) . . . . ?
C2 C1 N1 C8 174.49(19) . . . . ?
C2 C1 N1 Cu1 -2.2(3) . . . . ?
C13 C8 N1 C1 -88.5(2) . . . . ?
C9 C8 N1 C1 90.0(2) . . . . ?
C13 C8 N1 Cu1 88.28(19) . . . . ?
C9 C8 N1 Cu1 -93.2(2) . . . . ?
C2 C3 O1 Cu1 -8.1(3) . . . . ?
C4 C3 O1 Cu1 172.56(14) . . . . ?
C10 C11 O2 C14 175.1(2) . . . . ?
C12 C11 O2 C14 -4.3(4) . . . . ?
