#------------------------------------------------------------------------------
#$Date: 2023-09-15 01:57:56 +0300 (Fri, 15 Sep 2023) $
#$Revision: 286347 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/39/7713951.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_7713951
loop_
_publ_author_name
'Das, Athulya'
'Sankaralingam, Muniyandi'
_publ_section_title
;
 Are Zn(II) pincer complexes efficient apoptosis inducers? A deeper
 insight against A549 lung cancer cells
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D3DT02419A
_journal_year                    2023
_chemical_formula_sum            'C15 H18 Cl N3 O3 Zn'
_chemical_formula_weight         389.14
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-07-15 deposited with the CCDC.	2023-09-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.3813(4)
_cell_length_b                   14.5936(4)
_cell_length_c                   17.3975(6)
_cell_measurement_reflns_used    9579
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      69.43
_cell_measurement_theta_min      5.08
_cell_volume                     3143.51(17)
_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, 2012)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Venture Diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0863
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            66873
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.621
_diffrn_reflns_theta_min         5.084
_diffrn_source                   'micro focus sealed tube'
_exptl_absorpt_coefficient_mu    3.899
_exptl_absorpt_correction_T_max  0.7532
_exptl_absorpt_correction_T_min  0.5516
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2016/2 - Bruker'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.644
_exptl_crystal_description       plate
_exptl_crystal_F_000             1600
_exptl_crystal_size_max          0.142
_exptl_crystal_size_mid          0.137
_exptl_crystal_size_min          0.045
_refine_diff_density_max         0.808
_refine_diff_density_min         -0.676
_refine_diff_density_rms         0.108
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         2954
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0916
_refine_ls_R_factor_gt           0.0641
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0564P)²+20.6714P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1544
_refine_ls_wR_factor_ref         0.1820
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2186
_reflns_number_total             2954
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3dt02419a2.cif
_cod_data_source_block           shelx
_cod_original_cell_volume        3143.52(17)
_cod_database_code               7713951
_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   0.607
_shelx_estimated_absorpt_t_max   0.844
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -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
Zn1 Zn 0.10724(6) 0.36802(5) 0.06622(5) 0.0390(3) Uani 1 1 d . . . . .
C1 C -0.1394(5) 0.4076(5) 0.1046(4) 0.0523(16) Uani 1 1 d . . . . .
H1 H -0.129423 0.464425 0.081507 0.063 Uiso 1 1 calc R U . . .
C2 C -0.2428(5) 0.3843(5) 0.1304(4) 0.0543(17) Uani 1 1 d . . . . .
H2 H -0.300008 0.424835 0.124123 0.065 Uiso 1 1 calc R U . . .
C3 C -0.2587(5) 0.3017(5) 0.1646(4) 0.0517(16) Uani 1 1 d . . . . .
H3 H -0.327305 0.284993 0.181211 0.062 Uiso 1 1 calc R U . . .
C4 C -0.1708(5) 0.2415(4) 0.1750(4) 0.0460(14) Uani 1 1 d . . . . .
C5 C -0.1807(5) 0.1554(5) 0.2110(4) 0.0536(16) Uani 1 1 d . . . . .
H5 H -0.247144 0.135931 0.229783 0.064 Uiso 1 1 calc R U . . .
C6 C -0.0929(5) 0.1014(5) 0.2179(4) 0.0534(17) Uani 1 1 d . . . . .
H6 H -0.100179 0.045335 0.242740 0.064 Uiso 1 1 calc R U . . .
C7 C 0.0101(5) 0.1264(4) 0.1892(4) 0.0480(15) Uani 1 1 d . . . . .
H7 H 0.068607 0.086978 0.194800 0.058 Uiso 1 1 calc R U . . .
C8 C 0.0228(4) 0.2097(4) 0.1526(4) 0.0413(13) Uani 1 1 d . . . . .
C9 C -0.0687(4) 0.2683(4) 0.1468(3) 0.0399(13) Uani 1 1 d . . . . .
C10 C 0.2024(4) 0.1946(4) 0.1011(3) 0.0385(12) Uani 1 1 d . . . . .
C11 C 0.2916(4) 0.2470(4) 0.0603(4) 0.0407(13) Uani 1 1 d . . . . .
H11A H 0.360876 0.226287 0.079625 0.049 Uiso 1 1 calc R U . . .
H11B H 0.288789 0.232842 0.005829 0.049 Uiso 1 1 calc R U . . .
C12 C 0.3245(4) 0.3761(4) 0.1474(4) 0.0400(13) Uani 1 1 d . . . . .
H12A H 0.290168 0.338483 0.186302 0.048 Uiso 1 1 calc R U . . .
H12B H 0.303590 0.439222 0.156627 0.048 Uiso 1 1 calc R U . . .
C13 C 0.4461(5) 0.3679(4) 0.1556(4) 0.0495(15) Uani 1 1 d . . . . .
H13A H 0.467932 0.391573 0.205301 0.059 Uiso 1 1 calc R U . . .
H13B H 0.466594 0.303779 0.153216 0.059 Uiso 1 1 calc R U . . .
C14 C 0.4686(5) 0.3848(4) 0.0223(4) 0.0474(15) Uani 1 1 d . . . . .
H14A H 0.487487 0.320605 0.016733 0.057 Uiso 1 1 calc R U . . .
H14B H 0.507320 0.419117 -0.016755 0.057 Uiso 1 1 calc R U . . .
C15 C 0.3480(4) 0.3967(4) 0.0108(3) 0.0397(13) Uani 1 1 d . . . . .
H15A H 0.330453 0.461457 0.012510 0.048 Uiso 1 1 calc R U . . .
H15B H 0.328204 0.373805 -0.039630 0.048 Uiso 1 1 calc R U . . .
Cl1 Cl 0.07742(12) 0.35981(10) -0.06363(9) 0.0466(4) Uani 1 1 d . . . . .
N1 N -0.0550(4) 0.3525(3) 0.1116(3) 0.0431(11) Uani 1 1 d . . . . .
N2 N 0.1169(3) 0.2449(3) 0.1195(3) 0.0388(11) Uani 1 1 d . . . . .
N3 N 0.2843(3) 0.3477(3) 0.0702(3) 0.0356(10) Uani 1 1 d . . . . .
O1 O 0.1149(3) 0.5028(3) 0.0960(3) 0.0521(12) Uani 1 1 d D . . . .
H1B H 0.169(4) 0.537(5) 0.093(5) 0.078 Uiso 1 1 d D U . . .
H1A H 0.061(4) 0.536(5) 0.087(5) 0.078 Uiso 1 1 d D U . . .
O2 O 0.2147(3) 0.1096(3) 0.1097(3) 0.0504(11) Uani 1 1 d . . . . .
O3 O 0.5002(3) 0.4165(3) 0.0973(3) 0.0547(12) 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 0.0181 0.0091 '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 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn -1.5491 0.6778 '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
N2 Zn1 O1 137.6(2) . . ?
N2 Zn1 N1 78.18(17) . . ?
O1 Zn1 N1 92.95(18) . . ?
N2 Zn1 N3 78.96(17) . . ?
O1 Zn1 N3 94.34(16) . . ?
N1 Zn1 N3 153.05(19) . . ?
N2 Zn1 Cl1 114.46(15) . . ?
O1 Zn1 Cl1 107.97(16) . . ?
N1 Zn1 Cl1 101.77(15) . . ?
N3 Zn1 Cl1 100.56(13) . . ?
N1 C1 C2 123.0(6) . . ?
N1 C1 H1 118.5 . . ?
C2 C1 H1 118.5 . . ?
C3 C2 C1 119.3(6) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C2 C3 C4 119.8(6) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C3 C4 C5 123.1(6) . . ?
C3 C4 C9 118.3(6) . . ?
C5 C4 C9 118.6(6) . . ?
C6 C5 C4 119.4(6) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C5 C6 C7 123.0(6) . . ?
C5 C6 H6 118.5 . . ?
C7 C6 H6 118.5 . . ?
C8 C7 C6 119.4(6) . . ?
C8 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
C7 C8 N2 127.4(5) . . ?
C7 C8 C9 118.1(5) . . ?
N2 C8 C9 114.4(5) . . ?
N1 C9 C4 120.6(5) . . ?
N1 C9 C8 117.9(5) . . ?
C4 C9 C8 121.5(5) . . ?
O2 C10 N2 127.7(5) . . ?
O2 C10 C11 117.7(5) . . ?
N2 C10 C11 114.5(5) . . ?
N3 C11 C10 113.6(4) . . ?
N3 C11 H11A 108.9 . . ?
C10 C11 H11A 108.9 . . ?
N3 C11 H11B 108.9 . . ?
C10 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
N3 C12 C13 113.2(5) . . ?
N3 C12 H12A 108.9 . . ?
C13 C12 H12A 108.9 . . ?
N3 C12 H12B 108.9 . . ?
C13 C12 H12B 108.9 . . ?
H12A C12 H12B 107.8 . . ?
O3 C13 C12 111.4(5) . . ?
O3 C13 H13A 109.4 . . ?
C12 C13 H13A 109.4 . . ?
O3 C13 H13B 109.4 . . ?
C12 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
O3 C14 C15 110.5(5) . . ?
O3 C14 H14A 109.6 . . ?
C15 C14 H14A 109.6 . . ?
O3 C14 H14B 109.6 . . ?
C15 C14 H14B 109.6 . . ?
H14A C14 H14B 108.1 . . ?
N3 C15 C14 112.1(5) . . ?
N3 C15 H15A 109.2 . . ?
C14 C15 H15A 109.2 . . ?
N3 C15 H15B 109.2 . . ?
C14 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
C1 N1 C9 118.9(5) . . ?
C1 N1 Zn1 129.3(4) . . ?
C9 N1 Zn1 111.5(3) . . ?
C10 N2 C8 124.2(5) . . ?
C10 N2 Zn1 115.2(4) . . ?
C8 N2 Zn1 117.7(4) . . ?
C11 N3 C15 111.4(4) . . ?
C11 N3 C12 111.1(4) . . ?
C15 N3 C12 108.4(4) . . ?
C11 N3 Zn1 101.0(3) . . ?
C15 N3 Zn1 116.1(3) . . ?
C12 N3 Zn1 108.8(3) . . ?
Zn1 O1 H1B 126(6) . . ?
Zn1 O1 H1A 119(6) . . ?
H1B O1 H1A 106(8) . . ?
C13 O3 C14 111.3(4) . . ?
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
Zn1 N2 2.026(5) . ?
Zn1 O1 2.036(4) . ?
Zn1 N1 2.171(5) . ?
Zn1 N3 2.213(4) . ?
Zn1 Cl1 2.2921(18) . ?
C1 N1 1.324(7) . ?
C1 C2 1.398(9) . ?
C1 H1 0.9300 . ?
C2 C3 1.358(9) . ?
C2 H2 0.9300 . ?
C3 C4 1.410(9) . ?
C3 H3 0.9300 . ?
C4 C5 1.410(9) . ?
C4 C9 1.412(8) . ?
C5 C6 1.347(9) . ?
C5 H5 0.9300 . ?
C6 C7 1.417(8) . ?
C6 H6 0.9300 . ?
C7 C8 1.382(8) . ?
C7 H7 0.9300 . ?
C8 N2 1.397(7) . ?
C8 C9 1.423(8) . ?
C9 N1 1.382(7) . ?
C10 O2 1.260(7) . ?
C10 N2 1.328(7) . ?
C10 C11 1.519(8) . ?
C11 N3 1.482(7) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 N3 1.491(7) . ?
C12 C13 1.518(8) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 O3 1.407(8) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 O3 1.438(8) . ?
C14 C15 1.517(8) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 N3 1.485(7) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
O1 H1B 0.84(2) . ?
O1 H1A 0.84(2) . ?
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
C1 H1 Cl1 0.93 2.66 3.552(7) 160.3 5_565 yes
C2 H2 O3 0.93 2.52 3.269(7) 137.6 1_455 yes
C7 H7 O2 0.93 2.36 2.895(8) 116.4 . yes
C11 H11A Cl1 0.97 2.97 3.868(5) 153.7 3 yes
C12 H12B O2 0.97 2.63 3.503(7) 150.5 7_665 yes
C14 H14A Cl1 0.97 2.97 3.882(6) 156.7 3 yes
O1 H1B O2 0.84(2) 1.81(3) 2.635(6) 167(8) 7_665 yes
O1 H1A Cl1 0.84(2) 2.33(2) 3.163(4) 175(8) 5_565 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 C3 0.3(11) . . . . ?
C1 C2 C3 C4 1.1(10) . . . . ?
C2 C3 C4 C5 179.1(6) . . . . ?
C2 C3 C4 C9 -2.1(9) . . . . ?
C3 C4 C5 C6 179.3(6) . . . . ?
C9 C4 C5 C6 0.5(10) . . . . ?
C4 C5 C6 C7 -1.3(11) . . . . ?
C5 C6 C7 C8 0.5(11) . . . . ?
C6 C7 C8 N2 -178.6(6) . . . . ?
C6 C7 C8 C9 1.2(10) . . . . ?
C3 C4 C9 N1 1.6(9) . . . . ?
C5 C4 C9 N1 -179.5(6) . . . . ?
C3 C4 C9 C8 -177.7(6) . . . . ?
C5 C4 C9 C8 1.2(9) . . . . ?
C7 C8 C9 N1 178.6(6) . . . . ?
N2 C8 C9 N1 -1.5(8) . . . . ?
C7 C8 C9 C4 -2.0(9) . . . . ?
N2 C8 C9 C4 177.8(5) . . . . ?
O2 C10 C11 N3 -165.2(5) . . . . ?
N2 C10 C11 N3 18.6(7) . . . . ?
N3 C12 C13 O3 54.8(7) . . . . ?
O3 C14 C15 N3 -57.7(6) . . . . ?
C2 C1 N1 C9 -0.8(10) . . . . ?
C2 C1 N1 Zn1 173.1(5) . . . . ?
C4 C9 N1 C1 -0.2(9) . . . . ?
C8 C9 N1 C1 179.1(6) . . . . ?
C4 C9 N1 Zn1 -175.2(4) . . . . ?
C8 C9 N1 Zn1 4.2(7) . . . . ?
O2 C10 N2 C8 -0.1(10) . . . . ?
C11 C10 N2 C8 175.6(5) . . . . ?
O2 C10 N2 Zn1 -160.6(5) . . . . ?
C11 C10 N2 Zn1 15.1(6) . . . . ?
C7 C8 N2 C10 17.5(10) . . . . ?
C9 C8 N2 C10 -162.3(5) . . . . ?
C7 C8 N2 Zn1 177.6(5) . . . . ?
C9 C8 N2 Zn1 -2.2(7) . . . . ?
C10 C11 N3 C15 -161.4(5) . . . . ?
C10 C11 N3 C12 77.7(6) . . . . ?
C10 C11 N3 Zn1 -37.5(5) . . . . ?
C14 C15 N3 C11 -69.9(6) . . . . ?
C14 C15 N3 C12 52.6(6) . . . . ?
C14 C15 N3 Zn1 175.3(4) . . . . ?
C13 C12 N3 C11 71.6(6) . . . . ?
C13 C12 N3 C15 -51.1(6) . . . . ?
C13 C12 N3 Zn1 -178.1(4) . . . . ?
C12 C13 O3 C14 -57.9(6) . . . . ?
C15 C14 O3 C13 59.5(6) . . . . ?
