#------------------------------------------------------------------------------
#$Date: 2021-11-23 04:18:33 +0200 (Tue, 23 Nov 2021) $
#$Revision: 270821 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/39/7243960.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_7243960
loop_
_publ_author_name
'Alizadeh, Hanie'
'Mirzaei, Masoud'
'Saljooghi, Amir Sh.'
'Jodaian, Vida'
'Bazargan, Maryam'
'Mague, Joel T.'
'Gomila, Rosa M.'
'Frontera, Antonio'
_publ_section_title
;
 Coordination complexes of zinc and manganese based on
 pyridine-2,5-dicarboxylic acid N-oxide: DFT studies and antiproliferative
 activities consideration
;
_journal_issue                   59
_journal_name_full               'RSC Advances'
_journal_page_first              37403
_journal_page_last               37412
_journal_paper_doi               10.1039/D1RA08258B
_journal_volume                  11
_journal_year                    2021
_chemical_formula_moiety         'C17 H12 Cl N3 O5 Zn, 2(H2 O)'
_chemical_formula_sum            'C17 H16 Cl N3 O7 Zn'
_chemical_formula_weight         475.15
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-06-12 deposited with the CCDC.	2021-11-15 downloaded from the CCDC.
;
_cell_angle_alpha                75.923(2)
_cell_angle_beta                 84.467(2)
_cell_angle_gamma                80.995(2)
_cell_formula_units_Z            2
_cell_length_a                   8.5124(9)
_cell_length_b                   9.503(1)
_cell_length_c                   12.0869(13)
_cell_measurement_reflns_used    9931
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      29.2719
_cell_measurement_theta_min      2.2308
_cell_volume                     934.96(17)
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2012)'
_computing_publication_material  'SHELXTL (Bruker, 2016)'
_computing_structure_refinement
'SHELXL-2018/1 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Bruker Smart APEX CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            18159
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        28.500
_diffrn_reflns_theta_max         29.323
_diffrn_reflns_theta_min         1.740
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    1.504
_exptl_absorpt_correction_T_max  0.76
_exptl_absorpt_correction_T_min  0.69
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.688
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             484
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.218
_exptl_crystal_size_min          0.196
_exptl_transmission_factor_max   0.862
_exptl_transmission_factor_min   0.787
_refine_diff_density_max         0.583
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         5008
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.127
_refine_ls_R_factor_all          0.0287
_refine_ls_R_factor_gt           0.0255
_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)+(0.0403P)²+0.1335P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0708
_refine_ls_wR_factor_ref         0.0717
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4475
_reflns_number_total             5008
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ra08258b2.cif
_cod_data_source_block           JTM1270_0m_a
_cod_database_code               7243960
_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   0.705
_shelx_estimated_absorpt_t_max   0.757
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 0.44630(2) 0.36707(2) 0.33354(2) 0.01540(6) Uani 1 1 d . . . . .
Cl1 Cl 0.25153(4) 0.24150(4) 0.30770(3) 0.02207(8) Uani 1 1 d . . . . .
O1 O 0.32242(13) 0.56613(11) 0.33697(9) 0.0212(2) Uani 1 1 d . . . . .
O2 O 0.18122(12) 0.73570(11) 0.41856(9) 0.0216(2) Uani 1 1 d . . . . .
O3 O 0.46481(11) 0.34124(11) 0.50331(8) 0.0173(2) Uani 1 1 d . . . . .
O4 O 0.28547(13) 0.09385(12) 0.87629(9) 0.0246(2) Uani 1 1 d . . . . .
H4A H 0.262359 0.033002 0.940085 0.037 Uiso 1 1 d R U . . .
O5 O 0.04266(13) 0.20645(13) 0.91658(9) 0.0268(2) Uani 1 1 d . . . . .
N1 N 0.33632(13) 0.37645(12) 0.56820(10) 0.0141(2) Uani 1 1 d . . . . .
N2 N 0.57377(14) 0.46258(12) 0.18431(10) 0.0160(2) Uani 1 1 d . . . . .
N3 N 0.65776(14) 0.21607(13) 0.33408(10) 0.0170(2) Uani 1 1 d . . . . .
C1 C 0.24951(16) 0.60959(15) 0.42123(12) 0.0167(3) Uani 1 1 d . . . . .
C2 C 0.23152(16) 0.50172(14) 0.53593(11) 0.0151(3) Uani 1 1 d . . . . .
C3 C 0.10139(17) 0.52819(16) 0.61080(12) 0.0185(3) Uani 1 1 d . . . . .
H3 H 0.028914 0.615803 0.590692 0.022 Uiso 1 1 calc R U . . .
C4 C 0.07510(17) 0.43052(16) 0.71330(12) 0.0191(3) Uani 1 1 d . . . . .
H4 H -0.017108 0.447690 0.761677 0.023 Uiso 1 1 calc R U . . .
C5 C 0.18662(16) 0.30594(15) 0.74458(12) 0.0167(3) Uani 1 1 d . . . . .
C6 C 0.31758(16) 0.28282(15) 0.67090(11) 0.0160(3) Uani 1 1 d . . . . .
H6 H 0.395662 0.199802 0.692808 0.019 Uiso 1 1 calc R U . . .
C7 C 0.16437(17) 0.19660(16) 0.85479(12) 0.0194(3) Uani 1 1 d . . . . .
C8 C 0.52563(18) 0.59297(15) 0.11511(12) 0.0194(3) Uani 1 1 d . . . . .
H8 H 0.430506 0.649648 0.136372 0.023 Uiso 1 1 calc R U . . .
C9 C 0.60974(18) 0.64764(16) 0.01394(13) 0.0221(3) Uani 1 1 d . . . . .
H9 H 0.573745 0.740479 -0.033317 0.027 Uiso 1 1 calc R U . . .
C10 C 0.74750(19) 0.56378(18) -0.01669(13) 0.0241(3) Uani 1 1 d . . . . .
H10 H 0.806933 0.598372 -0.086014 0.029 Uiso 1 1 calc R U . . .
C11 C 0.79853(18) 0.42930(17) 0.05396(12) 0.0212(3) Uani 1 1 d . . . . .
H11 H 0.892962 0.370773 0.033865 0.025 Uiso 1 1 calc R U . . .
C12 C 0.70863(16) 0.38131(15) 0.15527(12) 0.0160(3) Uani 1 1 d . . . . .
C13 C 0.75572(16) 0.24173(15) 0.23889(12) 0.0159(3) Uani 1 1 d . . . . .
C14 C 0.89219(17) 0.14480(16) 0.22400(13) 0.0219(3) Uani 1 1 d . . . . .
H14 H 0.959449 0.163574 0.156143 0.026 Uiso 1 1 calc R U . . .
C15 C 0.92824(18) 0.02065(16) 0.30968(14) 0.0241(3) Uani 1 1 d . . . . .
H15 H 1.020735 -0.047047 0.301168 0.029 Uiso 1 1 calc R U . . .
C16 C 0.82880(19) -0.00437(16) 0.40788(14) 0.0233(3) Uani 1 1 d . . . . .
H16 H 0.852332 -0.088548 0.467944 0.028 Uiso 1 1 calc R U . . .
C17 C 0.69430(18) 0.09591(16) 0.41668(13) 0.0211(3) Uani 1 1 d . . . . .
H17 H 0.625380 0.078855 0.483789 0.025 Uiso 1 1 calc R U . . .
O6 O 0.25728(14) 0.89469(13) 0.05528(10) 0.0292(2) Uani 1 1 d . . . . .
H6A H 0.285724 0.906193 0.119383 0.044 Uiso 1 1 d R U . . .
H6B H 0.164386 0.865236 0.072686 0.044 Uiso 1 1 d R U . . .
O7 O 0.34711(13) 0.92270(12) 0.25522(10) 0.0276(2) Uani 1 1 d . . . . .
H7A H 0.321104 1.007596 0.272045 0.041 Uiso 1 1 d R U . . .
H7B H 0.295515 0.864164 0.307777 0.041 Uiso 1 1 d R U . . .
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'
Zn Zn 0.2839 1.4301 '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'
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 Zn1 O3 86.15(4) . . ?
O1 Zn1 N2 89.51(4) . . ?
O3 Zn1 N2 135.47(4) . . ?
O1 Zn1 N3 153.79(5) . . ?
O3 Zn1 N3 87.54(4) . . ?
N2 Zn1 N3 77.38(5) . . ?
O1 Zn1 Cl1 101.86(3) . . ?
O3 Zn1 Cl1 108.81(3) . . ?
N2 Zn1 Cl1 115.44(3) . . ?
N3 Zn1 Cl1 104.25(3) . . ?
C1 O1 Zn1 128.53(9) . . ?
N1 O3 Zn1 119.34(8) . . ?
C7 O4 H4A 108.0 . . ?
O3 N1 C6 115.79(11) . . ?
O3 N1 C2 122.79(11) . . ?
C6 N1 C2 121.38(11) . . ?
C8 N2 C12 119.42(12) . . ?
C8 N2 Zn1 124.55(10) . . ?
C12 N2 Zn1 115.95(9) . . ?
C17 N3 C13 119.18(12) . . ?
C17 N3 Zn1 125.25(10) . . ?
C13 N3 Zn1 115.44(9) . . ?
O2 C1 O1 125.34(13) . . ?
O2 C1 C2 114.55(12) . . ?
O1 C1 C2 120.01(12) . . ?
N1 C2 C3 118.01(12) . . ?
N1 C2 C1 122.70(11) . . ?
C3 C2 C1 119.28(12) . . ?
C4 C3 C2 121.66(13) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C3 C4 C5 118.65(13) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 H4 120.7 . . ?
C6 C5 C4 119.10(13) . . ?
C6 C5 C7 119.95(12) . . ?
C4 C5 C7 120.93(12) . . ?
N1 C6 C5 121.06(12) . . ?
N1 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
O5 C7 O4 125.07(14) . . ?
O5 C7 C5 121.53(14) . . ?
O4 C7 C5 113.40(12) . . ?
N2 C8 C9 122.34(13) . . ?
N2 C8 H8 118.8 . . ?
C9 C8 H8 118.8 . . ?
C10 C9 C8 118.39(14) . . ?
C10 C9 H9 120.8 . . ?
C8 C9 H9 120.8 . . ?
C9 C10 C11 119.85(14) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C10 C11 C12 118.77(13) . . ?
C10 C11 H11 120.6 . . ?
C12 C11 H11 120.6 . . ?
N2 C12 C11 121.23(13) . . ?
N2 C12 C13 115.64(12) . . ?
C11 C12 C13 123.10(12) . . ?
N3 C13 C14 121.43(13) . . ?
N3 C13 C12 114.87(11) . . ?
C14 C13 C12 123.68(13) . . ?
C15 C14 C13 118.85(14) . . ?
C15 C14 H14 120.6 . . ?
C13 C14 H14 120.6 . . ?
C14 C15 C16 119.61(13) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C15 C16 C17 118.53(14) . . ?
C15 C16 H16 120.7 . . ?
C17 C16 H16 120.7 . . ?
N3 C17 C16 122.39(14) . . ?
N3 C17 H17 118.8 . . ?
C16 C17 H17 118.8 . . ?
H6A O6 H6B 104.1 . . ?
H7A O7 H7B 104.0 . . ?
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 O1 2.0242(10) . ?
Zn1 O3 2.0251(10) . ?
Zn1 N2 2.0951(12) . ?
Zn1 N3 2.1186(12) . ?
Zn1 Cl1 2.2739(4) . ?
O1 C1 1.2632(16) . ?
O2 C1 1.2418(16) . ?
O3 N1 1.3309(14) . ?
O4 C7 1.3026(18) . ?
O4 H4A 0.8700 . ?
O5 C7 1.2225(17) . ?
N1 C6 1.3517(18) . ?
N1 C2 1.3688(17) . ?
N2 C8 1.3438(18) . ?
N2 C12 1.3469(17) . ?
N3 C17 1.3385(18) . ?
N3 C13 1.3493(17) . ?
C1 C2 1.5208(19) . ?
C2 C3 1.3927(18) . ?
C3 C4 1.378(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.3947(19) . ?
C4 H4 0.9500 . ?
C5 C6 1.3824(18) . ?
C5 C7 1.493(2) . ?
C6 H6 0.9500 . ?
C8 C9 1.384(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.384(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.385(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.3964(19) . ?
C11 H11 0.9500 . ?
C12 C13 1.4837(19) . ?
C13 C14 1.3913(19) . ?
C14 C15 1.383(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.383(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.384(2) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
O6 H6A 0.8698 . ?
O6 H6B 0.8697 . ?
O7 H7A 0.8697 . ?
O7 H7B 0.8698 . ?
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
O4 H4A O6 0.87 1.67 2.5239(16) 167 1_546 yes
C6 H6 O7 0.95 2.38 3.2645(18) 155 2_666 yes
C8 H8 O6 0.95 2.58 3.350(2) 138 . y
C11 H11 O5 0.95 2.49 3.3508(18) 151 1_654 yes
C15 H15 O2 0.95 2.49 3.2695(19) 139 1_645 y
O6 H6A O7 0.87 1.82 2.6886(17) 178 . yes
O6 H6B O5 0.87 1.97 2.8283(16) 170 2_566 yes
O7 H7A Cl1 0.87 2.34 3.2103(12) 177 1_565 yes
O7 H7B O2 0.87 1.89 2.7552(16) 178 . 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
Zn1 O3 N1 C6 138.55(10) . . . . ?
Zn1 O3 N1 C2 -43.63(15) . . . . ?
Zn1 O1 C1 O2 176.69(10) . . . . ?
Zn1 O1 C1 C2 -7.16(19) . . . . ?
O3 N1 C2 C3 -179.63(12) . . . . ?
C6 N1 C2 C3 -1.93(19) . . . . ?
O3 N1 C2 C1 2.06(19) . . . . ?
C6 N1 C2 C1 179.77(12) . . . . ?
O2 C1 C2 N1 -157.52(13) . . . . ?
O1 C1 C2 N1 25.9(2) . . . . ?
O2 C1 C2 C3 24.19(18) . . . . ?
O1 C1 C2 C3 -152.35(13) . . . . ?
N1 C2 C3 C4 -1.6(2) . . . . ?
C1 C2 C3 C4 176.77(13) . . . . ?
C2 C3 C4 C5 3.2(2) . . . . ?
C3 C4 C5 C6 -1.4(2) . . . . ?
C3 C4 C5 C7 179.86(13) . . . . ?
O3 N1 C6 C5 -178.40(12) . . . . ?
C2 N1 C6 C5 3.7(2) . . . . ?
C4 C5 C6 N1 -2.0(2) . . . . ?
C7 C5 C6 N1 176.71(12) . . . . ?
C6 C5 C7 O5 -172.85(13) . . . . ?
C4 C5 C7 O5 5.8(2) . . . . ?
C6 C5 C7 O4 7.24(19) . . . . ?
C4 C5 C7 O4 -174.07(13) . . . . ?
C12 N2 C8 C9 0.2(2) . . . . ?
Zn1 N2 C8 C9 -176.22(11) . . . . ?
N2 C8 C9 C10 0.5(2) . . . . ?
C8 C9 C10 C11 -0.6(2) . . . . ?
C9 C10 C11 C12 0.0(2) . . . . ?
C8 N2 C12 C11 -0.7(2) . . . . ?
Zn1 N2 C12 C11 175.99(10) . . . . ?
C8 N2 C12 C13 177.75(12) . . . . ?
Zn1 N2 C12 C13 -5.57(15) . . . . ?
C10 C11 C12 N2 0.6(2) . . . . ?
C10 C11 C12 C13 -177.73(13) . . . . ?
C17 N3 C13 C14 1.1(2) . . . . ?
Zn1 N3 C13 C14 -174.79(11) . . . . ?
C17 N3 C13 C12 -177.13(12) . . . . ?
Zn1 N3 C13 C12 6.96(15) . . . . ?
N2 C12 C13 N3 -0.98(17) . . . . ?
C11 C12 C13 N3 177.43(13) . . . . ?
N2 C12 C13 C14 -179.19(13) . . . . ?
C11 C12 C13 C14 -0.8(2) . . . . ?
N3 C13 C14 C15 -0.8(2) . . . . ?
C12 C13 C14 C15 177.31(13) . . . . ?
C13 C14 C15 C16 -0.1(2) . . . . ?
C14 C15 C16 C17 0.7(2) . . . . ?
C13 N3 C17 C16 -0.5(2) . . . . ?
Zn1 N3 C17 C16 174.93(11) . . . . ?
C15 C16 C17 N3 -0.3(2) . . . . ?
