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#$Date: 2022-01-20 11:57:57 +0200 (Thu, 20 Jan 2022) $
#$Revision: 272155 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/60/1566062.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_1566062
loop_
_publ_author_name
'Ji, Xiaoxi'
'Zhu, Xiaopeng'
'Chen, Shiyu'
'Song, Dongxue'
'Wu, Shuangyan'
'Zhang, Ying'
'Gao, Enjun'
'Xu, Jin'
'Zhu, Mingchang'
_publ_section_title
;
 Two Cu(II) and Zn(II) complexes derived from 5-(Pyrazol-1-yl)nicotinic
 acid: Crystal structure, DNA binding and anticancer studies
;
_journal_name_full               'Journal of Solid State Chemistry'
_journal_page_first              122707
_journal_paper_doi               10.1016/j.jssc.2021.122707
_journal_volume                  305
_journal_year                    2022
_chemical_formula_moiety         'C18 H12 N6 O4 Zn, 2(H2 O)'
_chemical_formula_sum            'C18 H17 N6 O6 Zn'
_chemical_formula_weight         478.74
_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   mixed
_atom_sites_solution_primary     dual
_cell_angle_alpha                90
_cell_angle_beta                 95.807(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.9796(12)
_cell_length_b                   10.0261(10)
_cell_length_c                   16.1223(18)
_cell_measurement_reflns_used    5517
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.419
_cell_measurement_theta_min      2.540
_cell_volume                     1926.5(3)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150.02
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0737
_diffrn_reflns_av_unetI/netI     0.0438
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            25632
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.426
_diffrn_reflns_theta_min         2.230
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.327
_exptl_absorpt_correction_T_max  0.0276
_exptl_absorpt_correction_T_min  0.0108
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0851 before and 0.0684 after correction. The Ratio of minimum to maximum transmission is 0.3913. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            'clear light blue'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.651
_exptl_crystal_description       needle
_exptl_crystal_F_000             980
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         3955
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0660
_refine_ls_R_factor_gt           0.0394
_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)+(0.0327P)²+1.8271P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0832
_refine_ls_wR_factor_ref         0.0946
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2861
_reflns_number_total             3955
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            JSSC-2022-305-122707.cif
_cod_data_source_block           mo_0912_7_0m
_cod_database_code               1566062
_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_max   0.857
_shelx_estimated_absorpt_t_min   0.816
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 O5-H5B
 0.89 with sigma of 0.01
3.a Free rotating group:
 O6(H6A,H6B)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C13(H13), C10(H10), C6(H6), C15(H15), C0AA(H0AA), C9(H9), C18(H18),
 C17(H17), C16(H16), C8(H8), C7(H7)
;
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
Zn1 Zn 0.50850(3) 0.55990(3) 0.25114(2) 0.02677(11) Uani 1 1 d . . . . .
O1 O 0.39982(16) 0.5023(2) 0.33006(13) 0.0320(5) Uani 1 1 d . . . . .
O3 O 0.86530(17) 0.8941(2) 0.23533(14) 0.0366(5) Uani 1 1 d . . . . .
O4 O 0.88618(17) 1.0289(2) 0.34332(14) 0.0380(5) Uani 1 1 d . . . . .
O2 O 0.35920(17) 0.3784(2) 0.21731(14) 0.0379(5) Uani 1 1 d . . . . .
N5 N 0.58903(19) 0.8611(2) 0.52936(15) 0.0292(6) Uani 1 1 d . . . . .
N2 N 0.10466(19) 0.3675(2) 0.52230(15) 0.0286(6) Uani 1 1 d . . . . .
N4 N 0.59885(19) 0.6984(2) 0.32619(15) 0.0285(6) Uani 1 1 d . . . . .
N1 N 0.09542(19) 0.1957(2) 0.32052(15) 0.0273(5) Uani 1 1 d . . . . .
N3 N 0.0245(2) 0.2961(3) 0.55718(16) 0.0326(6) Uani 1 1 d . . . . .
N6 N 0.5040(2) 0.7904(3) 0.55903(16) 0.0359(6) Uani 1 1 d . . . . .
C3 C 0.1813(2) 0.2547(3) 0.28736(19) 0.0277(6) Uani 1 1 d . . . . .
H3 H 0.197490 0.228998 0.233127 0.033 Uiso 1 1 calc R . . . .
C5 C 0.1338(2) 0.3309(3) 0.44234(18) 0.0268(6) Uani 1 1 d . . . . .
C13 C 0.7140(2) 0.8970(3) 0.42041(19) 0.0284(6) Uani 1 1 d . . . . .
H13 H 0.753336 0.964822 0.452469 0.034 Uiso 1 1 calc R . . . .
C11 C 0.7441(2) 0.8619(3) 0.34207(19) 0.0283(7) Uani 1 1 d . . . . .
C10 C 0.6851(2) 0.7627(3) 0.29724(19) 0.0286(7) Uani 1 1 d . . . . .
H10 H 0.706433 0.739164 0.243980 0.034 Uiso 1 1 calc R . . . .
C2 C 0.2471(2) 0.3516(3) 0.32956(18) 0.0282(7) Uani 1 1 d . . . . .
C14 C 0.6247(2) 0.8296(3) 0.45029(18) 0.0273(6) Uani 1 1 d . . . . .
C6 C 0.2225(2) 0.3918(3) 0.40810(18) 0.0286(7) Uani 1 1 d . . . . .
H6 H 0.265489 0.459393 0.437720 0.034 Uiso 1 1 calc R . . . .
C15 C 0.5689(2) 0.7305(3) 0.40212(18) 0.0278(6) Uani 1 1 d . . . . .
H15 H 0.508317 0.684544 0.423084 0.033 Uiso 1 1 calc R . . . .
C0AA C 0.0720(2) 0.2331(3) 0.39676(18) 0.0281(7) Uani 1 1 d . . . . .
H0AA H 0.011362 0.191630 0.420398 0.034 Uiso 1 1 calc R . . . .
C1 C 0.3418(2) 0.4147(3) 0.28916(19) 0.0298(7) Uani 1 1 d . . . . .
C9 C 0.0171(3) 0.3543(3) 0.63022(19) 0.0347(7) Uani 1 1 d . . . . .
H9 H -0.032641 0.326395 0.669141 0.042 Uiso 1 1 calc R . . . .
C12 C 0.8384(2) 0.9321(3) 0.30461(19) 0.0308(7) Uani 1 1 d . . . . .
C18 C 0.4942(3) 0.8410(3) 0.6342(2) 0.0357(7) Uani 1 1 d . . . . .
H18 H 0.441671 0.811071 0.670470 0.043 Uiso 1 1 calc R . . . .
C17 C 0.5716(3) 0.9441(3) 0.6531(2) 0.0374(7) Uani 1 1 d . . . . .
H17 H 0.581120 0.995870 0.702657 0.045 Uiso 1 1 calc R . . . .
C16 C 0.6303(2) 0.9545(3) 0.5852(2) 0.0347(7) Uani 1 1 d . . . . .
H16 H 0.689111 1.015808 0.578207 0.042 Uiso 1 1 calc R . . . .
C8 C 0.0911(3) 0.4613(3) 0.6430(2) 0.0353(7) Uani 1 1 d . . . . .
H8 H 0.101023 0.517950 0.690418 0.042 Uiso 1 1 calc R . . . .
C7 C 0.1460(3) 0.4673(3) 0.57319(19) 0.0343(7) Uani 1 1 d . . . . .
H7 H 0.202515 0.529586 0.562230 0.041 Uiso 1 1 calc R . . . .
O6 O 0.3614(2) 0.4095(3) 0.04827(15) 0.0534(7) Uani 1 1 d . . . . .
H6A H 0.420902 0.367192 0.035737 0.080 Uiso 1 1 d G . . . .
H6B H 0.357878 0.405882 0.101846 0.080 Uiso 1 1 d G . . . .
O5 O 0.2911(2) 0.6845(3) 0.4826(2) 0.0597(8) Uani 1 1 d D . . . .
H5A H 0.236(4) 0.764(5) 0.485(3) 0.12(2) Uiso 1 1 d . . . . .
H5B H 0.356(2) 0.710(4) 0.509(2) 0.083(16) Uiso 1 1 d 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'
Zn Zn 0.2839 1.4301 '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
O1 Zn1 O3 101.56(8) . 2_645
O1 Zn1 O4 154.08(9) . 2_645
O1 Zn1 N4 99.06(9) . .
O1 Zn1 N1 98.57(9) . 2
O1 Zn1 C1 28.31(9) . .
O1 Zn1 C12 129.48(10) . 2_645
O3 Zn1 C1 95.07(8) 2_645 .
O3 Zn1 C12 30.24(9) 2_645 2_645
O4 Zn1 O3 60.75(8) 2_645 2_645
O4 Zn1 N1 93.62(9) 2_645 2
O4 Zn1 C1 128.49(10) 2_645 .
O4 Zn1 C12 30.51(9) 2_645 2_645
N4 Zn1 O3 97.62(9) . 2_645
N4 Zn1 O4 101.91(9) . 2_645
N4 Zn1 N1 97.57(9) . 2
N4 Zn1 C1 127.36(10) . .
N4 Zn1 C12 101.31(9) . 2_645
N1 Zn1 O3 152.45(9) 2 2_645
N1 Zn1 C1 93.78(9) 2 .
N1 Zn1 C12 123.53(10) 2 2_645
C12 Zn1 C1 114.26(10) 2_645 .
C1 O1 Zn1 103.20(18) . .
C12 O3 Zn1 85.37(18) . 2_655
C12 O4 Zn1 91.78(18) . 2_655
N6 N5 C14 120.1(2) . .
C16 N5 N6 111.1(2) . .
C16 N5 C14 128.8(2) . .
N3 N2 C5 119.2(2) . .
C7 N2 N3 111.6(2) . .
C7 N2 C5 129.2(2) . .
C10 N4 Zn1 119.6(2) . .
C10 N4 C15 119.1(3) . .
C15 N4 Zn1 121.21(19) . .
C3 N1 Zn1 120.0(2) . 2_545
C0AA N1 Zn1 121.08(19) . 2_545
C0AA N1 C3 118.7(3) . .
C9 N3 N2 104.4(2) . .
C18 N6 N5 105.0(2) . .
N1 C3 C2 122.2(3) . .
C6 C5 N2 121.1(3) . .
C6 C5 C0AA 119.2(3) . .
C0AA C5 N2 119.7(3) . .
C14 C13 C11 118.0(3) . .
C13 C11 C12 121.2(3) . .
C10 C11 C13 119.4(3) . .
C10 C11 C12 119.4(3) . .
N4 C10 C11 122.4(3) . .
C3 C2 C6 119.3(3) . .
C3 C2 C1 119.9(3) . .
C6 C2 C1 120.8(3) . .
C13 C14 N5 120.9(3) . .
C15 C14 N5 119.3(3) . .
C15 C14 C13 119.8(3) . .
C5 C6 C2 118.5(3) . .
N4 C15 C14 121.3(3) . .
N1 C0AA C5 122.1(3) . .
O1 C1 Zn1 48.49(13) . .
O1 C1 C2 117.7(3) . .
O2 C1 Zn1 74.92(16) . .
O2 C1 O1 123.4(3) . .
O2 C1 C2 118.9(3) . .
C2 C1 Zn1 166.1(2) . .
N3 C9 C8 111.8(3) . .
O3 C12 Zn1 64.38(15) . 2_655
O3 C12 O4 122.1(3) . .
O3 C12 C11 119.0(3) . .
O4 C12 Zn1 57.71(14) . 2_655
O4 C12 C11 118.9(3) . .
C11 C12 Zn1 176.3(2) . 2_655
N6 C18 C17 111.2(3) . .
C16 C17 C18 105.4(3) . .
N5 C16 C17 107.3(3) . .
C7 C8 C9 105.4(3) . .
N2 C7 C8 106.8(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Zn1 O1 1.9957(19) .
Zn1 O3 2.243(2) 2_645
Zn1 O4 2.097(2) 2_645
Zn1 N4 2.073(2) .
Zn1 N1 2.109(2) 2
Zn1 C1 2.595(3) .
Zn1 C12 2.479(3) 2_645
O1 C1 1.264(4) .
O3 C12 1.253(4) .
O4 C12 1.259(4) .
O2 C1 1.251(4) .
N5 N6 1.367(3) .
N5 C14 1.421(4) .
N5 C16 1.357(4) .
N2 N3 1.364(3) .
N2 C5 1.417(4) .
N2 C7 1.356(4) .
N4 C10 1.341(3) .
N4 C15 1.349(4) .
N1 C3 1.344(3) .
N1 C0AA 1.342(4) .
N3 C9 1.325(4) .
N6 C18 1.330(4) .
C3 C2 1.386(4) .
C5 C6 1.388(4) .
C5 C0AA 1.392(4) .
C13 C11 1.393(4) .
C13 C14 1.392(4) .
C11 C10 1.381(4) .
C11 C12 1.509(4) .
C2 C6 1.388(4) .
C2 C1 1.503(4) .
C14 C15 1.390(4) .
C9 C8 1.393(4) .
C18 C17 1.401(4) .
C17 C16 1.364(4) .
C8 C7 1.362(4) .
