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#$Date: 2023-11-22 10:44:11 +0200 (Wed, 22 Nov 2023) $
#$Revision: 287723 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/76/8107651.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_8107651
loop_
_publ_author_name
'Li, Fenfang'
_publ_section_title
;
 Crystal structure of bis(dimethylammonium)
 poly[(μ4-1,1′-(1,4-phenylenebis(methylene))bis(1H-pyrazole-3,5-dicarboxylato))-κ6
 O 1, N 2:O 2:O 3:O 1′,N 2′]nickel (II)], C22H26N6NiO8
;
_journal_issue                   6
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1027
_journal_page_last               1029
_journal_paper_doi               10.1515/ncrs-2023-0120
_journal_volume                  238
_journal_year                    2023
_chemical_formula_sum            'C22 H26 N6 Ni O8'
_chemical_formula_weight         561.20
_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
_cell_angle_alpha                90
_cell_angle_beta                 116.5552(19)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.9372(7)
_cell_length_b                   10.4567(6)
_cell_length_c                   11.7618(7)
_cell_measurement_reflns_used    4520
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      26.70
_cell_measurement_theta_min      2.85
_cell_volume                     1203.25(13)
_computing_cell_refinement       'Bruker SAINT [1]'
_computing_data_collection       'SMART  (Bruker, 2002)[1]'
_computing_data_reduction        'Bruker SAINT [1]'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)[4]'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)[2-3]'
_diffrn_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0382
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8833
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.048
_diffrn_reflns_theta_max         25.048
_diffrn_reflns_theta_min         2.851
_exptl_absorpt_coefficient_mu    0.867
_exptl_absorpt_correction_T_max  0.7754
_exptl_absorpt_correction_T_min  0.6632
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker,2000)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.549
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.606
_refine_diff_density_min         -0.530
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       0.0069(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   0.947
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2113
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      0.977
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0406
_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)+(0.0494P)²+3.0873P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1028
_refine_ls_wR_factor_ref         0.1089
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1744
_reflns_number_total             2113
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2023-0120_suppl_001.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               8107651
_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   0.820
_shelx_estimated_absorpt_t_max   0.934
_publcif_funding_html
;
;
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
Ni1 Ni 0.5000 0.5000 0.0000 0.0177(2) Uani 1 2 d S . P . .
O1 O 0.5908(2) 0.3932(2) 0.1646(2) 0.0281(5) Uani 1 1 d . . . . .
O2 O 0.4348(3) 0.3483(3) 0.2317(3) 0.0672(11) Uani 1 1 d . . . . .
O3 O 0.8762(2) -0.0936(2) 0.5639(2) 0.0250(5) Uani 1 1 d . . . . .
O4 O 0.6731(3) -0.0846(3) 0.5641(3) 0.0454(7) Uani 1 1 d . . . . .
N1 N 0.7751(3) 0.2178(2) 0.3484(2) 0.0217(6) Uani 1 1 d . . . . .
N2 N 0.8274(3) 0.1169(2) 0.4248(2) 0.0205(6) Uani 1 1 d . . . . .
C1 C 0.7262(3) 0.0684(3) 0.4468(3) 0.0231(7) Uani 1 1 d . . . . .
C2 C 0.6078(3) 0.1396(3) 0.3832(3) 0.0288(8) Uani 1 1 d . . . . .
H2 H 0.5235 0.1256 0.3826 0.035 Uiso 1 1 calc R U . . .
C3 C 0.6406(3) 0.2353(3) 0.3212(3) 0.0257(7) Uani 1 1 d . . . . .
C4 C 0.8675(3) 0.2956(3) 0.3171(3) 0.0251(7) Uani 1 1 d . . . . .
H4A H 0.8163 0.3326 0.2333 0.030 Uiso 1 1 calc R U . . .
H4B H 0.9377 0.2409 0.3142 0.030 Uiso 1 1 calc R U . . .
C5 C 0.9352(3) 0.4021(3) 0.4119(3) 0.0260(7) Uani 1 1 d . . . . .
C6 C 1.0686(4) 0.3876(3) 0.5069(4) 0.0360(9) Uani 1 1 d . . . . .
H6 H 1.1156 0.3121 0.5119 0.043 Uiso 1 1 calc R U . . .
C7 C 0.8682(4) 0.5159(3) 0.4063(3) 0.0352(9) Uani 1 1 d . . . . .
H7 H 0.7793 0.5276 0.3432 0.042 Uiso 1 1 calc R U . . .
C8 C 0.7603(3) -0.0458(3) 0.5310(3) 0.0257(7) Uani 1 1 d . . . . .
C9 C 0.5479(4) 0.3355(3) 0.2314(3) 0.0318(8) Uani 1 1 d . . . . .
C10 C 0.0973(8) 0.2709(9) 0.1756(8) 0.123(3) Uani 1 1 d . U . . .
H10A H 0.0849 0.3310 0.1096 0.184 Uiso 1 1 calc R U . . .
H10B H 0.1088 0.3163 0.2507 0.184 Uiso 1 1 calc R U . . .
H10C H 0.0186 0.2164 0.1480 0.184 Uiso 1 1 calc R U . . .
N3 N 0.2193(5) 0.1928(5) 0.2041(5) 0.0853(17) Uani 1 1 d . . . . .
H3A H 0.2520 0.1588 0.2845 0.128 Uiso 1 1 d R U . . .
H3B H 0.2827 0.2498 0.2028 0.128 Uiso 1 1 d R U . . .
C11 C 0.2124(12) 0.0857(9) 0.1203(8) 0.157(4) Uani 1 1 d . . . . .
H11A H 0.1378 0.0305 0.1095 0.236 Uiso 1 1 calc R U . . .
H11B H 0.2964 0.0384 0.1577 0.236 Uiso 1 1 calc R U . . .
H11C H 0.1983 0.1183 0.0391 0.236 Uiso 1 1 calc 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'
Ni Ni 0.3393 1.1124 '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 Ni1 O1 180.0 3_665 .
O1 Ni1 O3 88.06(9) 3_665 4_565
O1 Ni1 O3 91.94(9) . 4_565
O1 Ni1 O3 91.94(9) 3_665 2_655
O1 Ni1 O3 88.06(9) . 2_655
O3 Ni1 O3 180.00(10) 4_565 2_655
O1 Ni1 N2 87.39(9) 3_665 4_565
O1 Ni1 N2 92.61(9) . 4_565
O3 Ni1 N2 79.38(9) 4_565 4_565
O3 Ni1 N2 100.62(9) 2_655 4_565
O1 Ni1 N2 92.61(9) 3_665 2_655
O1 Ni1 N2 87.39(9) . 2_655
O3 Ni1 N2 100.62(9) 4_565 2_655
O3 Ni1 N2 79.38(9) 2_655 2_655
N2 Ni1 N2 180.00(11) 4_565 2_655
C9 O1 Ni1 134.3(2) . .
C8 O3 Ni1 115.9(2) . 2_645
N2 N1 C3 110.8(3) . .
N2 N1 C4 118.0(3) . .
C3 N1 C4 130.9(3) . .
N1 N2 C1 106.6(2) . .
N1 N2 Ni1 141.4(2) . 2_645
C1 N2 Ni1 111.4(2) . 2_645
N2 C1 C2 110.2(3) . .
N2 C1 C8 116.7(3) . .
C2 C1 C8 133.2(3) . .
C3 C2 C1 105.9(3) . .
C3 C2 H2 127.1 . .
C1 C2 H2 127.1 . .
N1 C3 C2 106.6(3) . .
N1 C3 C9 124.8(3) . .
C2 C3 C9 128.4(3) . .
N1 C4 C5 112.8(3) . .
N1 C4 H4A 109.0 . .
C5 C4 H4A 109.0 . .
N1 C4 H4B 109.0 . .
C5 C4 H4B 109.0 . .
H4A C4 H4B 107.8 . .
C7 C5 C6 118.3(3) . .
C7 C5 C4 121.5(3) . .
C6 C5 C4 120.2(3) . .
C7 C6 C5 120.9(3) 3_766 .
C7 C6 H6 119.6 3_766 .
C5 C6 H6 119.6 . .
C6 C7 C5 120.9(3) 3_766 .
C6 C7 H7 119.6 3_766 .
C5 C7 H7 119.6 . .
O4 C8 O3 125.7(3) . .
O4 C8 C1 118.0(3) . .
O3 C8 C1 116.3(3) . .
O1 C9 O2 127.5(3) . .
O1 C9 C3 117.1(3) . .
O2 C9 C3 115.5(3) . .
N3 C10 H10A 109.5 . .
N3 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
N3 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
C11 N3 C10 120.0(7) . .
C11 N3 H3A 105.9 . .
C10 N3 H3A 110.2 . .
C11 N3 H3B 107.2 . .
C10 N3 H3B 104.5 . .
H3A N3 H3B 108.6 . .
N3 C11 H11A 109.5 . .
N3 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
N3 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ni1 O1 2.065(2) 3_665
Ni1 O1 2.065(2) .
Ni1 O3 2.065(2) 4_565
Ni1 O3 2.065(2) 2_655
Ni1 N2 2.085(2) 4_565
Ni1 N2 2.085(2) 2_655
O1 C9 1.238(4) .
O2 C9 1.245(4) .
O3 C8 1.253(4) .
O3 Ni1 2.065(2) 2_645
O4 C8 1.248(4) .
N1 N2 1.337(3) .
N1 C3 1.371(4) .
N1 C4 1.468(4) .
N2 C1 1.343(4) .
N2 Ni1 2.085(2) 2_645
C1 C2 1.388(5) .
C1 C8 1.489(5) .
C2 C3 1.376(5) .
C2 H2 0.9300 .
C3 C9 1.511(5) .
C4 C5 1.514(4) .
C4 H4A 0.9700 .
C4 H4B 0.9700 .
C5 C7 1.385(5) .
C5 C6 1.393(5) .
C6 C7 1.381(5) 3_766
C6 H6 0.9300 .
C7 C6 1.381(5) 3_766
C7 H7 0.9300 .
C10 N3 1.470(8) .
C10 H10A 0.9600 .
C10 H10B 0.9600 .
C10 H10C 0.9600 .
N3 C11 1.471(9) .
N3 H3A 0.9195 .
N3 H3B 0.9194 .
C11 H11A 0.9600 .
C11 H11B 0.9600 .
C11 H11C 0.9600 .
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
C2 H2 O4 0.93 2.53 3.443(4) 166.8 3_656
C4 H4A O1 0.97 2.31 2.926(4) 120.3 .
C4 H4B O3 0.97 2.44 3.282(4) 144.7 3_756
N3 H3A O4 0.92 1.77 2.689(5) 174.2 3_656
N3 H3B O2 0.92 1.85 2.760(6) 168.0 .
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
C3 N1 N2 C1 0.3(3) . . . .
C4 N1 N2 C1 175.2(3) . . . .
C3 N1 N2 Ni1 169.8(3) . . . 2_645
C4 N1 N2 Ni1 -15.3(4) . . . 2_645
N1 N2 C1 C2 0.0(4) . . . .
Ni1 N2 C1 C2 -173.0(2) 2_645 . . .
N1 N2 C1 C8 -179.8(3) . . . .
Ni1 N2 C1 C8 7.2(3) 2_645 . . .
N2 C1 C2 C3 -0.4(4) . . . .
C8 C1 C2 C3 179.4(3) . . . .
N2 N1 C3 C2 -0.5(4) . . . .
C4 N1 C3 C2 -174.6(3) . . . .
N2 N1 C3 C9 -176.2(3) . . . .
C4 N1 C3 C9 9.8(5) . . . .
C1 C2 C3 N1 0.5(4) . . . .
C1 C2 C3 C9 175.9(3) . . . .
N2 N1 C4 C5 -88.6(3) . . . .
C3 N1 C4 C5 85.0(4) . . . .
N1 C4 C5 C7 -80.9(4) . . . .
N1 C4 C5 C6 99.8(4) . . . .
C7 C5 C6 C7 0.5(6) . . . 3_766
C4 C5 C6 C7 179.8(3) . . . 3_766
C6 C5 C7 C6 -0.5(6) . . . 3_766
C4 C5 C7 C6 -179.8(3) . . . 3_766
Ni1 O3 C8 O4 -176.7(3) 2_645 . . .
Ni1 O3 C8 C1 2.2(4) 2_645 . . .
N2 C1 C8 O4 172.5(3) . . . .
C2 C1 C8 O4 -7.3(6) . . . .
N2 C1 C8 O3 -6.6(4) . . . .
C2 C1 C8 O3 173.7(3) . . . .
Ni1 O1 C9 O2 -17.0(6) . . . .
Ni1 O1 C9 C3 161.4(2) . . . .
N1 C3 C9 O1 10.7(5) . . . .
C2 C3 C9 O1 -164.0(4) . . . .
N1 C3 C9 O2 -170.8(4) . . . .
C2 C3 C9 O2 14.6(6) . . . .
