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#$Date: 2022-09-14 11:57:52 +0300 (Wed, 14 Sep 2022) $
#$Revision: 277826 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/57/8105768.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_8105768
loop_
_publ_author_name
'Jin, Lanlan'
'Tao, Defu'
'Hu, Rongyue'
'Pang, Haixia'
_publ_section_title
;
 Crystal structure of
 tetraqua-bis(4-(hydroxymethyl)benzoato-\kO)nickel(II), C16H22O10Ni
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              523
_journal_page_last               525
_journal_paper_doi               10.1515/ncrs-2018-0528
_journal_volume                  234
_journal_year                    2019
_chemical_formula_moiety         'C16 H22  O10 Ni'
_chemical_formula_sum            'C16 H22 Ni O10'
_chemical_formula_weight         433.04
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 122.253(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.7643(12)
_cell_length_b                   15.440(2)
_cell_length_c                   13.6274(13)
_cell_measurement_reflns_used    4165
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      31.35
_cell_measurement_theta_min      2.21
_cell_volume                     1737.5(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2 [1]'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014) [3]'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008) [2]'
_diffrn_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 0.997
_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  0.0319
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14021
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.000
_diffrn_reflns_theta_min         2.205
_exptl_absorpt_coefficient_mu    1.172
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.655
_exptl_crystal_description       block
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.787
_refine_diff_density_min         -0.684
_refine_diff_density_rms         0.095
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         3784
_refine_ls_number_restraints     14
_refine_ls_restrained_S_all      7.766
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0382
_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)+(0.0747P)²+0.6486P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1138
_refine_ls_wR_factor_ref         0.1282
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2822
_reflns_number_total             3784
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2018-0528_suppl.cif
_cod_data_source_block           mo_170412b_0m
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               8105768
_shelx_shelxl_version_number     2014/7
_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   0.872
_shelx_estimated_absorpt_t_max   0.892
_publcif_funding_html
;
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 0.5000 0.01846(14) Uani 1 2 d S . P . .
Ni2 Ni 0.0000 0.5000 0.5000 0.01906(14) Uani 1 2 d S . P . .
C1 C 0.6262(3) 0.37121(15) 0.81716(18) 0.0213(5) Uani 1 1 d . . . . .
C2 C 0.7006(3) 0.29902(15) 0.8859(2) 0.0257(5) Uani 1 1 d . . . . .
H2 H 0.7162 0.2500 0.8533 0.031 Uiso 1 1 calc R U . . .
C3 C 0.7521(3) 0.29852(17) 1.00220(19) 0.0281(6) Uani 1 1 d . . . . .
H3 H 0.8025 0.2496 1.0470 0.034 Uiso 1 1 calc R U . . .
C4 C 0.7290(3) 0.37060(16) 1.05225(19) 0.0262(5) Uani 1 1 d . . . . .
C5 C 0.6525(3) 0.44297(16) 0.9833(2) 0.0298(5) Uani 1 1 d . . . . .
H5 H 0.6358 0.4916 1.0159 0.036 Uiso 1 1 calc R U . . .
C6 C 0.6013(3) 0.44350(15) 0.8677(2) 0.0274(5) Uani 1 1 d . . . . .
H6 H 0.5498 0.4922 0.8228 0.033 Uiso 1 1 calc R U . . .
C7 C 0.5848(3) 0.37660(15) 0.69445(19) 0.0218(5) Uani 1 1 d . . . . .
C8 C 0.7787(4) 0.37497(17) 1.1784(2) 0.0392(7) Uani 1 1 d . . . . .
H8B H 0.8359 0.4290 1.2114 0.047 Uiso 1 1 calc DR U . . .
H8C H 0.6817 0.3759 1.1814 0.047 Uiso 1 1 calc R U . . .
C9 C 0.1340(3) 0.37310(15) 0.82159(19) 0.0231(5) Uani 1 1 d . . . . .
C10 C 0.2696(3) 0.33027(16) 0.9099(2) 0.0302(6) Uani 1 1 d . . . . .
H10 H 0.3432 0.3058 0.8945 0.036 Uiso 1 1 calc R U . . .
C11 C 0.2968(3) 0.32344(17) 1.0202(2) 0.0327(6) Uani 1 1 d . . . . .
H11 H 0.3891 0.2954 1.0783 0.039 Uiso 1 1 calc R U . . .
C12 C 0.1869(3) 0.35833(15) 1.04478(19) 0.0261(5) Uani 1 1 d . . . . .
C13 C 0.0490(3) 0.39856(16) 0.9563(2) 0.0294(5) Uani 1 1 d . . . . .
H13 H -0.0272 0.4205 0.9709 0.035 Uiso 1 1 calc R U . . .
C14 C 0.0235(3) 0.40647(16) 0.8469(2) 0.0288(5) Uani 1 1 d . . . . .
H14 H -0.0689 0.4345 0.7890 0.035 Uiso 1 1 calc R U . . .
C15 C 0.1111(3) 0.38522(14) 0.70446(19) 0.0219(5) Uani 1 1 d . . . . .
C16 C 0.2146(3) 0.35842(17) 1.1650(2) 0.0333(6) Uani 1 1 d . . . . .
H16A H 0.2254 0.4178 1.1914 0.040 Uiso 1 1 calc R U . . .
H16B H 0.1205 0.3337 1.1611 0.040 Uiso 1 1 calc R U . . .
O1 O 0.5001(2) 0.44050(10) 0.63485(13) 0.0257(4) Uani 1 1 d . . . . .
O2 O 0.6384(2) 0.31991(11) 0.65764(14) 0.0328(4) Uani 1 1 d . . . . .
O3 O 0.8777(2) 0.30601(12) 1.24781(15) 0.0366(5) Uani 1 1 d D . . . .
H3A H 0.825(4) 0.2611(14) 1.227(3) 0.055 Uiso 1 1 d D U . . .
O4 O 0.5628(2) 0.38537(10) 0.45498(14) 0.0237(4) Uani 1 1 d D . . . .
H4A H 0.593(3) 0.3556(15) 0.5133(13) 0.036 Uiso 1 1 d D U . . .
H4B H 0.498(3) 0.3580(15) 0.3968(14) 0.036 Uiso 1 1 d D U . . .
O5 O 0.7417(2) 0.52949(13) 0.60911(14) 0.0257(4) Uani 1 1 d D . . . .
H5A H 0.762(4) 0.5705(12) 0.582(2) 0.039 Uiso 1 1 d D U . . .
H5B H 0.794(4) 0.4864(12) 0.617(3) 0.039 Uiso 1 1 d D U . . .
O6 O 0.2007(2) 0.34526(12) 0.68045(14) 0.0344(4) Uani 1 1 d . . . . .
O7 O 0.00156(19) 0.43819(10) 0.63521(13) 0.0252(4) Uani 1 1 d . . . . .
O8 O 0.3537(2) 0.31143(12) 1.24719(15) 0.0346(4) Uani 1 1 d D . . . .
H8A H 0.331(4) 0.262(2) 1.239(3) 0.052 Uiso 1 1 d . U . . .
O9 O 0.0724(2) 0.38485(11) 0.45843(14) 0.0250(4) Uani 1 1 d D . . . .
H9A H 0.124(3) 0.3599(15) 0.5221(12) 0.037 Uiso 1 1 d D U . . .
H9B H 0.014(3) 0.3511(14) 0.4054(15) 0.037 Uiso 1 1 d D U . . .
O10 O 0.2394(2) 0.53301(12) 0.60926(14) 0.0255(4) Uani 1 1 d D . . . .
H10A H 0.289(4) 0.4874(11) 0.623(3) 0.038 Uiso 1 1 d D U . . .
H10B H 0.270(3) 0.5694(13) 0.582(2) 0.038 Uiso 1 1 d D 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'
Ni Ni 0.3393 1.1124 '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'
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_666
O1 Ni1 O5 89.99(7) . .
O1 Ni1 O5 90.01(7) 3_666 .
O1 Ni1 O5 90.01(7) . 3_666
O1 Ni1 O5 89.99(7) 3_666 3_666
O5 Ni1 O5 180.0 . 3_666
O1 Ni1 O4 88.63(6) . 3_666
O1 Ni1 O4 91.37(6) 3_666 3_666
O5 Ni1 O4 90.20(7) . 3_666
O5 Ni1 O4 89.80(7) 3_666 3_666
O1 Ni1 O4 91.37(6) . .
O1 Ni1 O4 88.63(6) 3_666 .
O5 Ni1 O4 89.80(7) . .
O5 Ni1 O4 90.20(7) 3_666 .
O4 Ni1 O4 180.0 3_666 .
O10 Ni2 O10 180.0 . 3_566
O10 Ni2 O7 89.76(7) . 3_566
O10 Ni2 O7 90.24(7) 3_566 3_566
O10 Ni2 O7 90.24(7) . .
O10 Ni2 O7 89.76(7) 3_566 .
O7 Ni2 O7 180.0 3_566 .
O10 Ni2 O9 89.36(7) . .
O10 Ni2 O9 90.64(7) 3_566 .
O7 Ni2 O9 89.64(6) 3_566 .
O7 Ni2 O9 90.36(6) . .
O10 Ni2 O9 90.64(7) . 3_566
O10 Ni2 O9 89.36(7) 3_566 3_566
O7 Ni2 O9 90.36(6) 3_566 3_566
O7 Ni2 O9 89.64(6) . 3_566
O9 Ni2 O9 180.00(11) . 3_566
C2 C1 C6 118.4(2) . .
C2 C1 C7 122.1(2) . .
C6 C1 C7 119.4(2) . .
C3 C2 C1 121.2(2) . .
C3 C2 H2 119.4 . .
C1 C2 H2 119.4 . .
C2 C3 C4 120.3(2) . .
C2 C3 H3 119.9 . .
C4 C3 H3 119.9 . .
C3 C4 C5 118.8(2) . .
C3 C4 C8 123.8(2) . .
C5 C4 C8 117.4(2) . .
C6 C5 C4 120.9(2) . .
C6 C5 H5 119.6 . .
C4 C5 H5 119.6 . .
C5 C6 C1 120.5(2) . .
C5 C6 H6 119.8 . .
C1 C6 H6 119.8 . .
O2 C7 O1 123.9(2) . .
O2 C7 C1 119.1(2) . .
O1 C7 C1 117.0(2) . .
O3 C8 C4 114.6(2) . .
O3 C8 H8B 108.6 . .
C4 C8 H8B 108.6 . .
O3 C8 H8C 108.6 . .
C4 C8 H8C 108.6 . .
H8B C8 H8C 107.6 . .
C10 C9 C14 117.8(2) . .
C10 C9 C15 120.8(2) . .
C14 C9 C15 121.4(2) . .
C11 C10 C9 121.2(2) . .
C11 C10 H10 119.4 . .
C9 C10 H10 119.4 . .
C10 C11 C12 120.4(2) . .
C10 C11 H11 119.8 . .
C12 C11 H11 119.8 . .
C13 C12 C11 118.7(2) . .
C13 C12 C16 118.1(2) . .
C11 C12 C16 123.1(2) . .
C14 C13 C12 120.7(2) . .
C14 C13 H13 119.6 . .
C12 C13 H13 119.6 . .
C13 C14 C9 121.1(2) . .
C13 C14 H14 119.4 . .
C9 C14 H14 119.4 . .
O6 C15 O7 123.5(2) . .
O6 C15 C9 119.3(2) . .
O7 C15 C9 117.2(2) . .
O8 C16 C12 113.5(2) . .
O8 C16 H16A 108.9 . .
C12 C16 H16A 108.9 . .
O8 C16 H16B 108.9 . .
C12 C16 H16B 108.9 . .
H16A C16 H16B 107.7 . .
C7 O1 Ni1 127.68(14) . .
C8 O3 H3A 109(3) . .
Ni1 O4 H4A 102(2) . .
Ni1 O4 H4B 122(2) . .
H4A O4 H4B 110(2) . .
Ni1 O5 H5A 108(2) . .
Ni1 O5 H5B 108(2) . .
H5A O5 H5B 114(2) . .
C15 O7 Ni2 124.04(14) . .
C16 O8 H8A 108(3) . .
Ni2 O9 H9A 102.3(19) . .
Ni2 O9 H9B 127(2) . .
H9A O9 H9B 112(2) . .
Ni2 O10 H10A 105(2) . .
Ni2 O10 H10B 113(2) . .
H10A O10 H10B 113(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ni1 O1 2.0542(15) .
Ni1 O1 2.0542(15) 3_666
Ni1 O5 2.0600(17) .
Ni1 O5 2.0600(17) 3_666
Ni1 O4 2.0702(16) 3_666
Ni1 O4 2.0702(16) .
Ni2 O10 2.0556(17) .
Ni2 O10 2.0556(17) 3_566
Ni2 O7 2.0678(15) 3_566
Ni2 O7 2.0678(15) .
Ni2 O9 2.1000(17) .
Ni2 O9 2.1000(17) 3_566
C1 C2 1.386(3) .
C1 C6 1.399(3) .
C1 C7 1.498(3) .
C2 C3 1.383(3) .
C2 H2 0.9300 .
C3 C4 1.385(3) .
C3 H3 0.9300 .
C4 C5 1.393(3) .
C4 C8 1.518(3) .
C5 C6 1.375(3) .
C5 H5 0.9300 .
C6 H6 0.9300 .
C7 O2 1.254(3) .
C7 O1 1.265(3) .
C8 O3 1.410(3) .
C8 H8B 0.9700 .
C8 H8C 0.9700 .
C9 C10 1.392(3) .
C9 C14 1.394(3) .
C9 C15 1.501(3) .
C10 C11 1.384(3) .
C10 H10 0.9300 .
C11 C12 1.392(4) .
C11 H11 0.9300 .
C12 C13 1.386(3) .
C12 C16 1.512(3) .
C13 C14 1.380(3) .
C13 H13 0.9300 .
C14 H14 0.9300 .
C15 O6 1.248(3) .
C15 O7 1.275(3) .
C16 O8 1.415(3) .
C16 H16A 0.9700 .
C16 H16B 0.9700 .
O3 H3A 0.817(10) .
O4 H4A 0.824(9) .
O4 H4B 0.820(10) .
O5 H5A 0.812(10) .
O5 H5B 0.811(10) .
O8 H8A 0.79(3) .
O9 H9A 0.830(9) .
O9 H9B 0.824(10) .
O10 H10A 0.817(10) .
O10 H10B 0.811(10) .
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
O10 H10B O4 0.811(10) 2.075(17) 2.809(2) 151(3) 3_666
O10 H10A O6 0.817(10) 2.62(2) 3.143(3) 123(2) .
O10 H10A O1 0.817(10) 2.11(2) 2.774(2) 138(3) .
O9 H9B O3 0.824(10) 1.954(12) 2.741(2) 159(3) 1_454
O9 H9A O6 0.830(9) 1.882(14) 2.656(2) 155(3) .
O8 H8A O6 0.79(3) 1.97(3) 2.732(3) 160(4) 4_566
O5 H5B O7 0.811(10) 2.04(2) 2.755(2) 146(3) 1_655
O5 H5A O9 0.812(10) 2.08(2) 2.770(2) 143(3) 3_666
O4 H4B O8 0.820(10) 1.895(10) 2.705(2) 169(3) 1_554
O4 H4A O2 0.824(9) 1.855(13) 2.649(2) 161(3) .
O3 H3A O2 0.817(10) 1.987(15) 2.772(3) 161(4) 4_566
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
C6 C1 C2 C3 -1.2(4) . . . .
C7 C1 C2 C3 173.6(2) . . . .
C1 C2 C3 C4 0.5(4) . . . .
C2 C3 C4 C5 0.3(4) . . . .
C2 C3 C4 C8 178.8(2) . . . .
C3 C4 C5 C6 -0.4(4) . . . .
C8 C4 C5 C6 -178.9(2) . . . .
C4 C5 C6 C1 -0.4(4) . . . .
C2 C1 C6 C5 1.2(4) . . . .
C7 C1 C6 C5 -173.8(2) . . . .
C2 C1 C7 O2 -10.1(3) . . . .
C6 C1 C7 O2 164.7(2) . . . .
C2 C1 C7 O1 171.8(2) . . . .
C6 C1 C7 O1 -13.4(3) . . . .
C3 C4 C8 O3 11.2(4) . . . .
C5 C4 C8 O3 -170.4(2) . . . .
C14 C9 C10 C11 -2.1(4) . . . .
C15 C9 C10 C11 176.0(2) . . . .
C9 C10 C11 C12 1.1(4) . . . .
C10 C11 C12 C13 1.1(4) . . . .
C10 C11 C12 C16 -175.8(2) . . . .
C11 C12 C13 C14 -2.1(4) . . . .
C16 C12 C13 C14 174.9(2) . . . .
C12 C13 C14 C9 1.1(4) . . . .
C10 C9 C14 C13 1.0(4) . . . .
C15 C9 C14 C13 -177.0(2) . . . .
C10 C9 C15 O6 11.1(3) . . . .
C14 C9 C15 O6 -170.9(2) . . . .
C10 C9 C15 O7 -167.4(2) . . . .
C14 C9 C15 O7 10.6(3) . . . .
C13 C12 C16 O8 176.6(2) . . . .
C11 C12 C16 O8 -6.5(4) . . . .
O2 C7 O1 Ni1 -27.1(3) . . . .
C1 C7 O1 Ni1 150.98(15) . . . .
O6 C15 O7 Ni2 -22.0(3) . . . .
C9 C15 O7 Ni2 156.43(15) . . . .
