#------------------------------------------------------------------------------
#$Date: 2022-11-07 12:58:22 +0200 (Mon, 07 Nov 2022) $
#$Revision: 279031 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/51/1565163.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_1565163
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         'C22 H30 Cl2 N4 O2 Zn, 0.5(H2 O)'
_chemical_formula_sum            'C22 H31 Cl2 N4 O2.5 Zn'
_chemical_formula_weight         527.77
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_cell_angle_alpha                90
_cell_angle_beta                 122.071(7)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   29.965(4)
_cell_length_b                   8.0447(12)
_cell_length_c                   23.742(4)
_cell_measurement_reflns_used    5454
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.651
_cell_measurement_theta_min      3.481
_cell_volume                     4849.8(13)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2016)'
_computing_data_collection       'Bruker Apex3, 2016'
_computing_data_reduction        'SAINT V8.38A (Bruker, 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      100.0
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0653
_diffrn_reflns_av_unetI/netI     0.0583
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            15452
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        66.860
_diffrn_reflns_theta_max         66.860
_diffrn_reflns_theta_min         3.481
_diffrn_source                   'high brilliance microfocus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.665
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6573
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0741 before and 0.0615 after correction. The Ratio of minimum to maximum transmission is 0.8731. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_description       block
_exptl_crystal_F_000             2200
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.527
_refine_diff_density_rms         0.085
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4279
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0766
_refine_ls_R_factor_gt           0.0452
_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)+(0.0290P)²+16.1725P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0909
_refine_ls_wR_factor_ref         0.1033
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3077
_reflns_number_total             4279
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ICA-2020-506-1195465.cif
_cod_data_source_block           js109_7
_cod_depositor_comments
;

2022-11-07
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C44 H62 Cl4 N8 O5 Zn2'
_cod_original_formula_weight         1055.55
_cod_original_formula_moiety         '2(C22 H30 Cl2 N4 O2 Zn), H2 O'
_cod_original_formula_units_Z            4
_cod_original_cell_volume        4849.9(12)
_cod_database_code               1565163
_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   0.758
_shelx_estimated_absorpt_t_min   0.711
_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, All O(H) groups
2.a Riding coordinates:
 O3(H3A)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C7(H7A,H7B), C6(H6A,H6B), C17(H17A,H17B), C15(H15A,H15B),
 C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C20(H20), C13(H13), C3(H3), C10(H10), C12(H12), C11(H11)
2.d Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C22(H22A,H22B,H22C), C2(H2A,H2B,H2C), C19(H19A,H19B,H19C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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 0.40646(2) 0.73555(6) 0.83788(2) 0.02268(14) Uani 1 1 d . . . . .
Cl2 Cl 0.48783(4) 0.66512(13) 0.86183(5) 0.0312(2) Uani 1 1 d . . . . .
Cl1 Cl 0.35485(4) 0.51164(13) 0.79788(5) 0.0313(2) Uani 1 1 d . . . . .
O2 O 0.34666(11) 0.4535(3) 0.49410(14) 0.0306(7) Uani 1 1 d . . . . .
O1 O 0.38264(10) 0.8827(3) 0.62752(13) 0.0282(6) Uani 1 1 d . . . . .
N3 N 0.41677(12) 0.1649(4) 0.42350(15) 0.0233(7) Uani 1 1 d . . . . .
N2 N 0.38746(11) 1.0212(4) 0.74089(15) 0.0232(7) Uani 1 1 d . . . . .
N4 N 0.42412(12) 0.2574(4) 0.47655(15) 0.0250(7) Uani 1 1 d . . . . .
N1 N 0.36853(11) 0.9203(4) 0.77019(15) 0.0228(7) Uani 1 1 d . . . . .
O3 O 0.500000 0.4087(7) 0.750000 0.0687(16) Uani 1 2 d S T P . .
H3A H 0.494320 0.454950 0.784020 0.103 Uiso 1 1 d R . . . .
C20 C 0.44081(15) 0.0009(5) 0.5113(2) 0.0281(9) Uani 1 1 d . . . . .
H20 H 0.449716 -0.095668 0.538248 0.034 Uiso 1 1 calc R . . . .
C14 C 0.28992(15) 0.6983(5) 0.4638(2) 0.0276(9) Uani 1 1 d . . . . .
C9 C 0.32321(15) 0.8119(5) 0.51335(19) 0.0260(9) Uani 1 1 d . . . . .
C18 C 0.43869(15) 0.1598(5) 0.5300(2) 0.0282(9) Uani 1 1 d . . . . .
C13 C 0.25165(15) 0.7576(6) 0.4012(2) 0.0345(10) Uani 1 1 d . . . . .
H13 H 0.228566 0.680995 0.367896 0.041 Uiso 1 1 calc R . . . .
C3 C 0.31168(15) 1.1275(5) 0.7156(2) 0.0283(9) Uani 1 1 d . . . . .
H3 H 0.281707 1.197665 0.698466 0.034 Uiso 1 1 calc R . . . .
C8 C 0.36455(15) 0.7499(5) 0.58056(19) 0.0288(9) Uani 1 1 d . . . . .
H8A H 0.349847 0.660143 0.594484 0.035 Uiso 1 1 calc R . . . .
H8B H 0.394425 0.703689 0.578841 0.035 Uiso 1 1 calc R . . . .
C4 C 0.35348(15) 1.1463(5) 0.70655(19) 0.0250(9) Uani 1 1 d . . . . .
C1 C 0.32194(14) 0.9872(5) 0.75433(19) 0.0255(9) Uani 1 1 d . . . . .
C7 C 0.42058(15) 0.8279(5) 0.69225(19) 0.0278(9) Uani 1 1 d . . . . .
H7A H 0.452733 0.790226 0.693959 0.033 Uiso 1 1 calc R . . . .
H7B H 0.406493 0.733555 0.704954 0.033 Uiso 1 1 calc R . . . .
C6 C 0.43349(14) 0.9719(5) 0.73949(19) 0.0266(9) Uani 1 1 d . . . . .
H6A H 0.462111 0.939210 0.784726 0.032 Uiso 1 1 calc R . . . .
H6B H 0.446014 1.067313 0.725197 0.032 Uiso 1 1 calc R . . . .
C10 C 0.31745(16) 0.9811(5) 0.4982(2) 0.0307(10) Uani 1 1 d . . . . .
H10 H 0.339809 1.059252 0.531281 0.037 Uiso 1 1 calc R . . . .
C5 C 0.36369(18) 1.2733(6) 0.6693(2) 0.0380(11) Uani 1 1 d . . . . .
H5A H 0.398490 1.322834 0.698673 0.057 Uiso 1 1 calc GR . . . .
H5B H 0.336697 1.360123 0.653226 0.057 Uiso 1 1 calc GR . . . .
H5C H 0.362630 1.220618 0.631364 0.057 Uiso 1 1 calc GR . . . .
C17 C 0.41446(16) 0.4357(5) 0.4698(2) 0.0278(9) Uani 1 1 d . . . . .
H17A H 0.424593 0.481025 0.439382 0.033 Uiso 1 1 calc R . . . .
H17B H 0.437239 0.488686 0.513772 0.033 Uiso 1 1 calc R . . . .
C15 C 0.29550(16) 0.5138(5) 0.4761(2) 0.0318(10) Uani 1 1 d . . . . .
H15A H 0.289405 0.487364 0.512234 0.038 Uiso 1 1 calc R . . . .
H15B H 0.268233 0.455747 0.435468 0.038 Uiso 1 1 calc R . . . .
C16 C 0.35777(16) 0.4817(6) 0.4437(2) 0.0321(10) Uani 1 1 d . . . . .
H16A H 0.351818 0.600172 0.430345 0.039 Uiso 1 1 calc R . . . .
H16B H 0.334007 0.413536 0.404079 0.039 Uiso 1 1 calc R . . . .
C21 C 0.42749(15) 0.0067(5) 0.4455(2) 0.0262(9) Uani 1 1 d . . . . .
C12 C 0.24656(16) 0.9255(6) 0.3865(2) 0.0322(10) Uani 1 1 d . . . . .
H12 H 0.220730 0.963890 0.343311 0.039 Uiso 1 1 calc R . . . .
C11 C 0.27943(16) 1.0362(6) 0.4353(2) 0.0331(10) Uani 1 1 d . . . . .
H11 H 0.276009 1.151849 0.425709 0.040 Uiso 1 1 calc R . . . .
C22 C 0.42577(17) -0.1335(5) 0.4034(2) 0.0353(10) Uani 1 1 d . . . . .
H22A H 0.389071 -0.165501 0.372115 0.053 Uiso 1 1 calc GR . . . .
H22B H 0.445171 -0.228492 0.431801 0.053 Uiso 1 1 calc GR . . . .
H22C H 0.441943 -0.098643 0.378690 0.053 Uiso 1 1 calc GR . . . .
C2 C 0.29006(16) 0.9127(6) 0.7793(2) 0.0368(11) Uani 1 1 d . . . . .
H2A H 0.290396 0.791303 0.776012 0.055 Uiso 1 1 calc GR . . . .
H2B H 0.253726 0.953068 0.752431 0.055 Uiso 1 1 calc GR . . . .
H2C H 0.305116 0.944728 0.825788 0.055 Uiso 1 1 calc GR . . . .
C19 C 0.45055(18) 0.2274(6) 0.5949(2) 0.0387(11) Uani 1 1 d . . . . .
H19A H 0.482950 0.293473 0.615026 0.058 Uiso 1 1 calc GR . . . .
H19B H 0.455178 0.135402 0.624565 0.058 Uiso 1 1 calc GR . . . .
H19C H 0.421328 0.297968 0.587788 0.058 Uiso 1 1 calc GR . . . .
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
Cl1 Zn1 Cl2 108.41(4) . .
N3 Zn1 Cl2 105.89(9) 6_566 .
N3 Zn1 Cl1 116.28(9) 6_566 .
N1 Zn1 Cl2 117.18(9) . .
N1 Zn1 Cl1 106.45(10) . .
N1 Zn1 N3 102.99(13) . 6_566
C16 O2 C15 112.7(3) . .
C7 O1 C8 111.7(3) . .
N4 N3 Zn1 124.3(2) . 6_565
C21 N3 Zn1 129.2(3) . 6_565
C21 N3 N4 105.5(3) . .
N1 N2 C6 120.2(3) . .
C4 N2 N1 111.3(3) . .
C4 N2 C6 127.5(3) . .
N3 N4 C17 120.4(3) . .
C18 N4 N3 111.1(3) . .
C18 N4 C17 128.4(3) . .
N2 N1 Zn1 128.6(2) . .
C1 N1 Zn1 124.9(3) . .
C1 N1 N2 105.5(3) . .
C18 C20 H20 126.4 . .
C18 C20 C21 107.3(4) . .
C21 C20 H20 126.4 . .
C9 C14 C15 121.6(4) . .
C13 C14 C9 119.2(4) . .
C13 C14 C15 119.2(4) . .
C14 C9 C8 119.7(4) . .
C10 C9 C14 118.9(4) . .
C10 C9 C8 121.4(4) . .
N4 C18 C20 106.7(4) . .
N4 C18 C19 122.7(4) . .
C20 C18 C19 130.6(4) . .
C14 C13 H13 119.3 . .
C12 C13 C14 121.4(4) . .
C12 C13 H13 119.3 . .
C4 C3 H3 126.5 . .
C1 C3 H3 126.5 . .
C1 C3 C4 106.9(4) . .
O1 C8 C9 109.9(3) . .
O1 C8 H8A 109.7 . .
O1 C8 H8B 109.7 . .
C9 C8 H8A 109.7 . .
C9 C8 H8B 109.7 . .
H8A C8 H8B 108.2 . .
N2 C4 C3 106.1(3) . .
N2 C4 C5 122.9(3) . .
C3 C4 C5 131.0(4) . .
N1 C1 C3 110.0(3) . .
N1 C1 C2 121.0(4) . .
C3 C1 C2 128.9(4) . .
O1 C7 H7A 110.1 . .
O1 C7 H7B 110.1 . .
O1 C7 C6 108.0(3) . .
H7A C7 H7B 108.4 . .
C6 C7 H7A 110.1 . .
C6 C7 H7B 110.1 . .
N2 C6 C7 110.7(3) . .
N2 C6 H6A 109.5 . .
N2 C6 H6B 109.5 . .
C7 C6 H6A 109.5 . .
C7 C6 H6B 109.5 . .
H6A C6 H6B 108.1 . .
C9 C10 H10 119.7 . .
C11 C10 C9 120.6(4) . .
C11 C10 H10 119.7 . .
C4 C5 H5A 109.5 . .
C4 C5 H5B 109.5 . .
C4 C5 H5C 109.5 . .
H5A C5 H5B 109.5 . .
H5A C5 H5C 109.5 . .
H5B C5 H5C 109.5 . .
N4 C17 H17A 108.8 . .
N4 C17 H17B 108.8 . .
N4 C17 C16 113.6(3) . .
H17A C17 H17B 107.7 . .
C16 C17 H17A 108.8 . .
C16 C17 H17B 108.8 . .
O2 C15 C14 112.4(3) . .
O2 C15 H15A 109.1 . .
O2 C15 H15B 109.1 . .
C14 C15 H15A 109.1 . .
C14 C15 H15B 109.1 . .
H15A C15 H15B 107.9 . .
O2 C16 C17 109.2(3) . .
O2 C16 H16A 109.8 . .
O2 C16 H16B 109.8 . .
C17 C16 H16A 109.8 . .
C17 C16 H16B 109.8 . .
H16A C16 H16B 108.3 . .
N3 C21 C20 109.5(4) . .
N3 C21 C22 122.6(4) . .
C20 C21 C22 127.9(4) . .
C13 C12 H12 120.5 . .
C11 C12 C13 119.1(4) . .
C11 C12 H12 120.5 . .
C10 C11 H11 119.6 . .
C12 C11 C10 120.8(4) . .
C12 C11 H11 119.6 . .
C21 C22 H22A 109.5 . .
C21 C22 H22B 109.5 . .
C21 C22 H22C 109.5 . .
H22A C22 H22B 109.5 . .
H22A C22 H22C 109.5 . .
H22B C22 H22C 109.5 . .
C1 C2 H2A 109.5 . .
C1 C2 H2B 109.5 . .
C1 C2 H2C 109.5 . .
H2A C2 H2B 109.5 . .
H2A C2 H2C 109.5 . .
H2B C2 H2C 109.5 . .
C18 C19 H19A 109.5 . .
C18 C19 H19B 109.5 . .
C18 C19 H19C 109.5 . .
H19A C19 H19B 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Zn1 Cl2 2.2623(11) .
Zn1 Cl1 2.2313(11) .
Zn1 N3 2.050(3) 6_566
Zn1 N1 2.036(3) .
O2 C15 1.440(5) .
O2 C16 1.421(5) .
O1 C8 1.427(5) .
O1 C7 1.412(4) .
N3 N4 1.376(4) .
N3 C21 1.348(5) .
N2 N1 1.372(4) .
N2 C4 1.354(5) .
N2 C6 1.452(4) .
N4 C18 1.352(5) .
N4 C17 1.455(5) .
N1 C1 1.350(5) .
O3 H3A 0.9828 .
C20 H20 0.9500 .
C20 C18 1.365(6) .
C20 C21 1.394(6) .
C14 C9 1.402(6) .
C14 C13 1.394(6) .
C14 C15 1.505(6) .
C9 C8 1.493(5) .
C9 C10 1.395(6) .
C18 C19 1.489(6) .
C13 H13 0.9500 .
C13 C12 1.384(6) .
C3 H3 0.9500 .
C3 C4 1.387(5) .
C3 C1 1.384(6) .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C4 C5 1.486(6) .
C1 C2 1.491(5) .
C7 H7A 0.9900 .
C7 H7B 0.9900 .
C7 C6 1.513(5) .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C10 H10 0.9500 .
C10 C11 1.385(6) .
C5 H5A 0.9800 .
C5 H5B 0.9800 .
C5 H5C 0.9800 .
C17 H17A 0.9900 .
C17 H17B 0.9900 .
C17 C16 1.513(5) .
C15 H15A 0.9900 .
C15 H15B 0.9900 .
C16 H16A 0.9900 .
C16 H16B 0.9900 .
C21 C22 1.489(6) .
C12 H12 0.9500 .
C12 C11 1.376(6) .
C11 H11 0.9500 .
C22 H22A 0.9800 .
C22 H22B 0.9800 .
C22 H22C 0.9800 .
C2 H2A 0.9800 .
C2 H2B 0.9800 .
C2 H2C 0.9800 .
C19 H19A 0.9800 .
C19 H19B 0.9800 .
C19 H19C 0.9800 .
