#------------------------------------------------------------------------------
#$Date: 2021-11-10 11:59:37 +0200 (Wed, 10 Nov 2021) $
#$Revision: 270563 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/51/1565160.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_1565160
loop_
_publ_author_name
'Soldevila-Sanmartín, Joan'
'Guerrero, Miguel'
'Choquesillo-Lazarte, Duane'
'Giner Planas, José'
'Pons, Josefina'
_publ_section_title
;
 Dimeric metallacycles and coordination polymers: Zn(II), Cd(II) and
 Hg(II) complexes of two positional isomers of a flexible N,O-hybrid
 bispyrazole derived ligand
;
_journal_name_full               'Inorganica Chimica Acta'
_journal_page_first              119549
_journal_paper_doi               10.1016/j.ica.2020.119549
_journal_volume                  506
_journal_year                    2020
_chemical_formula_moiety         'C44 H60 Cl4 N8 O4 Zn2'
_chemical_formula_sum            'C44 H60 Cl4 N8 O4 Zn2'
_chemical_formula_weight         1037.54
_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
_cell_angle_alpha                90
_cell_angle_beta                 96.203(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.5030(4)
_cell_length_b                   19.1113(9)
_cell_length_c                   13.3218(6)
_cell_measurement_reflns_used    9968
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.73
_cell_measurement_theta_min      2.19
_cell_volume                     2405.27(19)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.959
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_device_type  'Single-axis Bruker MD2M diffractometer'
_diffrn_measurement_method       'φ scans'
_diffrn_radiation_detector       'Dectris PILATUS 6M'
_diffrn_radiation_monochromator  'Si 111'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_wavelength     0.72932
_diffrn_reflns_av_R_equivalents  0.0516
_diffrn_reflns_av_unetI/netI     0.0437
_diffrn_reflns_Laue_measured_fraction_full 0.959
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            17476
_diffrn_reflns_point_group_measured_fraction_full 0.959
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        25.773
_diffrn_reflns_theta_max         25.773
_diffrn_reflns_theta_min         1.920
_diffrn_source                   synchrotron
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.353
_exptl_absorpt_correction_T_max  0.0189
_exptl_absorpt_correction_T_min  0.0048
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1878 before and 0.0757 after correction. The Ratio of minimum to maximum transmission is 0.2540. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_description       block
_exptl_crystal_F_000             1080
_refine_diff_density_max         1.134
_refine_diff_density_min         -0.723
_refine_diff_density_rms         0.119
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         4097
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0457
_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)+(0.1014P)²+0.4394P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1320
_refine_ls_wR_factor_ref         0.1344
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3906
_reflns_number_total             4097
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ICA-2020-506-1195462.cif
_cod_data_source_block           js98_a
_cod_database_code               1565160
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C11(H11A,H11B), C18(H18A,H18B), C20(H20A,H20B),
 C21(H21A,H21B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C13(H13), C14(H14), C16(H16), C17(H17), C25(H25)
2.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C7(H7A,H7B,H7C), C24(H24A,H24B,H24C), C27(H27A,H27B,H27C)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
C3 C 0.2030(3) 0.48265(15) 0.8271(2) 0.0503(6) Uani 1 1 d . . . . .
C4 C 0.1395(3) 0.5041(2) 0.9202(3) 0.0697(9) Uani 1 1 d . . . . .
H4A H 0.039334 0.490859 0.913893 0.105 Uiso 1 1 calc GR . . . .
H4B H 0.147991 0.554941 0.928758 0.105 Uiso 1 1 calc GR . . . .
H4C H 0.189571 0.480686 0.979014 0.105 Uiso 1 1 calc GR . . . .
C5 C 0.2540(3) 0.52212(14) 0.7526(2) 0.0519(6) Uani 1 1 d . . . . .
H5 H 0.258564 0.571728 0.749676 0.062 Uiso 1 1 calc R . . . .
C6 C 0.2974(3) 0.47512(14) 0.68244(19) 0.0468(6) Uani 1 1 d . . . . .
C7 C 0.3647(4) 0.49140(16) 0.5889(2) 0.0618(8) Uani 1 1 d . . . . .
H7A H 0.465981 0.480623 0.599941 0.093 Uiso 1 1 calc GR . . . .
H7B H 0.351896 0.541160 0.572624 0.093 Uiso 1 1 calc GR . . . .
H7C H 0.320260 0.463123 0.532840 0.093 Uiso 1 1 calc GR . . . .
C8 C 0.1930(3) 0.35250(15) 0.86072(19) 0.0463(6) Uani 1 1 d . . . . .
H8A H 0.145456 0.316013 0.816519 0.056 Uiso 1 1 calc R . . . .
H8B H 0.130164 0.364404 0.912817 0.056 Uiso 1 1 calc R . . . .
C9 C 0.3304(3) 0.32386(13) 0.9114(2) 0.0454(6) Uani 1 1 d . . . . .
H9A H 0.313959 0.278062 0.942870 0.054 Uiso 1 1 calc R . . . .
H9B H 0.398519 0.317042 0.861045 0.054 Uiso 1 1 calc R . . . .
C11 C 0.5355(3) 0.36467(14) 1.00959(18) 0.0450(5) Uani 1 1 d . . . . .
H11A H 0.558304 0.314433 1.019530 0.054 Uiso 1 1 calc R . . . .
H11B H 0.566308 0.389389 1.073496 0.054 Uiso 1 1 calc R . . . .
C12 C 0.6156(3) 0.39332(13) 0.92686(18) 0.0407(5) Uani 1 1 d . . . . .
C13 C 0.5731(3) 0.45622(13) 0.88093(19) 0.0434(5) Uani 1 1 d . . . . .
H13 H 0.491928 0.479531 0.900313 0.052 Uiso 1 1 calc R . . . .
C14 C 0.6473(3) 0.48559(13) 0.80713(19) 0.0435(5) Uani 1 1 d . . . . .
H14 H 0.616377 0.528631 0.776596 0.052 Uiso 1 1 calc R . . . .
C15 C 0.7669(3) 0.45237(13) 0.77747(17) 0.0408(5) Uani 1 1 d . . . . .
C16 C 0.8078(3) 0.38922(13) 0.82204(19) 0.0441(5) Uani 1 1 d . . . . .
H16 H 0.887725 0.365409 0.801610 0.053 Uiso 1 1 calc R . . . .
C17 C 0.7336(3) 0.35985(13) 0.89659(19) 0.0438(5) Uani 1 1 d . . . . .
H17 H 0.764141 0.316661 0.926825 0.053 Uiso 1 1 calc R . . . .
C18 C 0.8467(3) 0.48435(14) 0.69759(19) 0.0454(6) Uani 1 1 d . . . . .
H18A H 0.947406 0.470122 0.708266 0.054 Uiso 1 1 calc R . . . .
H18B H 0.806636 0.467923 0.630012 0.054 Uiso 1 1 calc R . . . .
C20 C 0.9089(3) 0.59415(14) 0.6318(2) 0.0465(6) Uani 1 1 d . . . . .
H20A H 0.885914 0.573624 0.563736 0.056 Uiso 1 1 calc R . . . .
H20B H 1.012408 0.590774 0.650308 0.056 Uiso 1 1 calc R . . . .
C21 C 0.8621(3) 0.66979(13) 0.6322(2) 0.0437(6) Uani 1 1 d . . . . .
H21A H 0.882283 0.688899 0.701312 0.052 Uiso 1 1 calc R . . . .
H21B H 0.917310 0.697230 0.587064 0.052 Uiso 1 1 calc R . . . .
C23 C 0.6049(3) 0.68295(11) 0.6576(2) 0.0438(6) Uani 1 1 d . . . . .
C24 C 0.6282(4) 0.68855(16) 0.7694(2) 0.0569(7) Uani 1 1 d . . . . .
H24A H 0.686753 0.649301 0.796678 0.085 Uiso 1 1 calc GR . . . .
H24B H 0.536773 0.687317 0.797123 0.085 Uiso 1 1 calc GR . . . .
H24C H 0.676397 0.732713 0.788249 0.085 Uiso 1 1 calc GR . . . .
C25 C 0.4816(3) 0.68329(13) 0.5931(2) 0.0494(7) Uani 1 1 d . . . . .
H25 H 0.388058 0.686446 0.611691 0.059 Uiso 1 1 calc R . . . .
C26 C 0.5196(3) 0.67817(12) 0.4959(2) 0.0460(6) Uani 1 1 d . . . . .
C27 C 0.4271(3) 0.67736(17) 0.3969(3) 0.0627(8) Uani 1 1 d . . . . .
H27A H 0.435682 0.722151 0.362291 0.094 Uiso 1 1 calc GR . . . .
H27B H 0.328367 0.670076 0.409319 0.094 Uiso 1 1 calc GR . . . .
H27C H 0.456955 0.639329 0.354658 0.094 Uiso 1 1 calc GR . . . .
Cl1 Cl -0.00761(6) 0.33152(3) 0.59093(5) 0.04512(19) Uani 1 1 d . . . . .
Cl2 Cl 0.29625(7) 0.21937(3) 0.69963(5) 0.0466(2) Uani 1 1 d . . . . .
N1 N 0.2738(2) 0.40902(11) 0.71136(14) 0.0403(4) Uani 1 1 d . . . . .
N2 N 0.2145(2) 0.41464(11) 0.80058(15) 0.0427(5) Uani 1 1 d . . . . .
N22 N 0.7128(2) 0.67766(9) 0.59934(18) 0.0391(5) Uani 1 1 d . . . . .
N28 N 0.6620(2) 0.67428(10) 0.49941(16) 0.0402(5) Uani 1 1 d . . . . .
O10 O 0.38603(18) 0.37251(10) 0.98666(12) 0.0460(4) Uani 1 1 d . . . . .
O19 O 0.8358(2) 0.55799(10) 0.70328(14) 0.0520(5) Uani 1 1 d . . . . .
Zn1 Zn 0.22861(3) 0.32128(2) 0.62363(2) 0.03790(16) 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 0.0040 0.0020 '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 0.1550 0.1690 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0070 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0120 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2970 1.5350 '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
C5 C3 C4 130.8(3) . .
N2 C3 C4 122.1(3) . .
N2 C3 C5 107.0(2) . .
C3 C4 H4A 109.5 . .
C3 C4 H4B 109.5 . .
C3 C4 H4C 109.5 . .
H4A C4 H4B 109.5 . .
H4A C4 H4C 109.5 . .
H4B C4 H4C 109.5 . .
C3 C5 H5 126.7 . .
C3 C5 C6 106.5(2) . .
C6 C5 H5 126.7 . .
C5 C6 C7 127.7(3) . .
N1 C6 C5 110.0(2) . .
N1 C6 C7 122.3(2) . .
C6 C7 H7A 109.5 . .
C6 C7 H7B 109.5 . .
C6 C7 H7C 109.5 . .
H7A C7 H7B 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
H8A C8 H8B 107.9 . .
C9 C8 H8A 109.2 . .
C9 C8 H8B 109.2 . .
N2 C8 H8A 109.2 . .
N2 C8 H8B 109.2 . .
N2 C8 C9 112.1(2) . .
C8 C9 H9A 110.0 . .
C8 C9 H9B 110.0 . .
H9A C9 H9B 108.4 . .
O10 C9 C8 108.4(2) . .
O10 C9 H9A 110.0 . .
O10 C9 H9B 110.0 . .
H11A C11 H11B 107.9 . .
C12 C11 H11A 109.2 . .
C12 C11 H11B 109.2 . .
O10 C11 H11A 109.2 . .
O10 C11 H11B 109.2 . .
O10 C11 C12 111.98(19) . .
C13 C12 C11 119.4(2) . .
C17 C12 C11 122.2(2) . .
C17 C12 C13 118.4(2) . .
C12 C13 H13 119.5 . .
C14 C13 C12 121.1(2) . .
C14 C13 H13 119.5 . .
C13 C14 H14 119.7 . .
C13 C14 C15 120.5(2) . .
C15 C14 H14 119.7 . .
C14 C15 C18 120.3(2) . .
C16 C15 C14 118.4(2) . .
C16 C15 C18 121.3(2) . .
C15 C16 H16 119.5 . .
C15 C16 C17 121.1(2) . .
C17 C16 H16 119.5 . .
C12 C17 C16 120.5(2) . .
C12 C17 H17 119.8 . .
C16 C17 H17 119.8 . .
C15 C18 H18A 109.9 . .
C15 C18 H18B 109.9 . .
H18A C18 H18B 108.3 . .
O19 C18 C15 108.75(19) . .
O19 C18 H18A 109.9 . .
O19 C18 H18B 109.9 . .
H20A C20 H20B 108.5 . .
C21 C20 H20A 110.3 . .
C21 C20 H20B 110.3 . .
O19 C20 H20A 110.3 . .
O19 C20 H20B 110.3 . .
O19 C20 C21 107.3(2) . .
C20 C21 H21A 109.2 . .
C20 C21 H21B 109.2 . .
H21A C21 H21B 107.9 . .
N22 C21 C20 112.2(2) . .
N22 C21 H21A 109.2 . .
N22 C21 H21B 109.2 . .
C25 C23 C24 130.6(2) . .
N22 C23 C24 122.6(3) . .
N22 C23 C25 106.8(2) . .
C23 C24 H24A 109.5 . .
C23 C24 H24B 109.5 . .
C23 C24 H24C 109.5 . .
H24A C24 H24B 109.5 . .
H24A C24 H24C 109.5 . .
H24B C24 H24C 109.5 . .
C23 C25 H25 126.5 . .
C23 C25 C26 107.0(2) . .
C26 C25 H25 126.5 . .
C25 C26 C27 129.3(3) . .
N28 C26 C25 109.5(3) . .
N28 C26 C27 121.2(2) . .
C26 C27 H27A 109.5 . .
C26 C27 H27B 109.5 . .
C26 C27 H27C 109.5 . .
H27A C27 H27B 109.5 . .
H27A C27 H27C 109.5 . .
H27B C27 H27C 109.5 . .
C6 N1 N2 105.72(19) . .
C6 N1 Zn1 129.17(16) . .
N2 N1 Zn1 118.30(14) . .
C3 N2 C8 128.1(2) . .
C3 N2 N1 110.7(2) . .
N1 N2 C8 120.41(19) . .
C23 N22 C21 127.8(2) . .
C23 N22 N28 110.6(2) . .
N28 N22 C21 121.4(2) . .
C26 N28 N22 106.1(2) . .
C26 N28 Zn1 124.52(19) . 3_666
N22 N28 Zn1 128.69(17) . 3_666
C9 O10 C11 111.5(2) . .
C18 O19 C20 113.89(19) . .
Cl1 Zn1 Cl2 113.09(2) . .
N1 Zn1 Cl1 100.45(6) . .
N1 Zn1 Cl2 114.57(6) . .
N28 Zn1 Cl1 115.23(7) 3_666 .
N28 Zn1 Cl2 104.59(6) 3_666 .
N28 Zn1 N1 109.23(8) 3_666 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C3 C4 1.494(4) .
C3 C5 1.376(4) .
C3 N2 1.355(3) .
C4 H4A 0.9800 .
C4 H4B 0.9800 .
C4 H4C 0.9800 .
C5 H5 0.9500 .
C5 C6 1.391(4) .
C6 C7 1.493(4) .
C6 N1 1.347(3) .
C7 H7A 0.9800 .
C7 H7B 0.9800 .
C7 H7C 0.9800 .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C8 C9 1.506(4) .
C8 N2 1.459(3) .
C9 H9A 0.9900 .
C9 H9B 0.9900 .
C9 O10 1.426(3) .
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C11 C12 1.508(3) .
C11 O10 1.428(3) .
C12 C13 1.389(4) .
C12 C17 1.389(4) .
C13 H13 0.9500 .
C13 C14 1.389(3) .
C14 H14 0.9500 .
C14 C15 1.396(3) .
C15 C16 1.382(4) .
C15 C18 1.502(3) .
C16 H16 0.9500 .
C16 C17 1.396(4) .
C17 H17 0.9500 .
C18 H18A 0.9900 .
C18 H18B 0.9900 .
C18 O19 1.414(3) .
C20 H20A 0.9900 .
C20 H20B 0.9900 .
C20 C21 1.513(4) .
C20 O19 1.418(3) .
C21 H21A 0.9900 .
C21 H21B 0.9900 .
C21 N22 1.447(4) .
C23 C24 1.487(4) .
C23 C25 1.376(4) .
C23 N22 1.355(3) .
C24 H24A 0.9800 .
C24 H24B 0.9800 .
C24 H24C 0.9800 .
C25 H25 0.9500 .
C25 C26 1.384(4) .
C26 C27 1.504(5) .
C26 N28 1.351(4) .
C27 H27A 0.9800 .
C27 H27B 0.9800 .
C27 H27C 0.9800 .
Cl1 Zn1 2.2485(7) .
Cl2 Zn1 2.2563(7) .
N1 N2 1.374(3) .
N1 Zn1 2.062(2) .
N22 N28 1.367(3) .
N28 Zn1 2.035(2) 3_666
