#------------------------------------------------------------------------------
#$Date: 2023-06-21 11:51:19 +0300 (Wed, 21 Jun 2023) $
#$Revision: 284515 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/74/8107407.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_8107407
loop_
_publ_author_name
'Xiao, Pan-Lei'
'Xiong, Xin-Ting'
'Ou-Yang, Xiao-Hui'
'Ren, Yue'
'Nie, Xu-Liang'
_publ_section_title
;
 Crystal structure of triaqua-[5-bromo-2-(carboxylatomethoxy)benzoate-κ 3
 O,O′,O″]nickel(II), C9H11BrNiO8
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              247
_journal_page_last               248
_journal_paper_doi               10.1515/ncrs-2022-0582
_journal_volume                  238
_journal_year                    2023
_chemical_formula_sum            'C9 H11 Br Ni O8'
_chemical_formula_weight         385.80
_chemical_name_systematic
'triaqua-[5-Bromo-2-carboxylatophenoxyacetato-k³ O,O',O'']nickel(II)'
_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                 98.188(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.5077(16)
_cell_length_b                   6.7688(13)
_cell_length_c                   22.459(4)
_cell_measurement_reflns_used    4998
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.14
_cell_measurement_theta_min      2.82
_cell_volume                     1280.2(4)
_computing_cell_refinement       'APEX2, SAINT and SADABS [1]'
_computing_data_collection       'APEX2, SAINT and SADABS [1]'
_computing_data_reduction        'APEX2, SAINT and SADABS [1]'
_computing_molecular_graphics    'Diamond 4.0 [4]'
_computing_publication_material  'SHELXL-2019/1 (Sheldrick, 2019) [3]'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019) [3]'
_computing_structure_solution    'XT, VERSION 2018/2 [2]'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_av_unetI/netI     0.0194
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            10749
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         2.819
_exptl_absorpt_coefficient_mu    4.668
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.002
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.450
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         2910
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0256
_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)+(0.0200P)²+1.1608P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0560
_refine_ls_wR_factor_ref         0.0585
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2510
_reflns_number_total             2910
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2022-0582_suppl.cif
_cod_data_source_block           A
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               8107407
_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   0.228
_shelx_estimated_absorpt_t_max   0.522
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 0.23071(3) 0.18457(4) 0.20361(2) 0.02340(8) Uani 1 1 d . . . . .
O1 O 0.4458(2) -0.3125(2) 0.14519(7) 0.0360(4) Uani 1 1 d . . . . .
O2 O 0.34418(19) -0.0634(2) 0.18926(7) 0.0309(4) Uani 1 1 d . . . . .
O3 O 0.19227(19) 0.2247(2) 0.10964(6) 0.0272(3) Uani 1 1 d . . . . .
O4 O -0.0121(2) 0.6667(2) 0.13655(7) 0.0350(4) Uani 1 1 d . . . . .
O5 O 0.10979(19) 0.4418(2) 0.19922(7) 0.0309(4) Uani 1 1 d . . . . .
O6 O 0.43991(19) 0.3392(2) 0.20871(7) 0.0329(4) Uani 1 1 d D . . . .
H1W H 0.4314 0.4449 0.1906 0.043(8) Uiso 1 1 d DR . . . .
H2W H 0.5043 0.3469 0.2398 0.059(10) Uiso 1 1 d DR . . . .
O7 O 0.01744(19) 0.0334(2) 0.19539(7) 0.0333(4) Uani 1 1 d D . . . .
H3W H -0.0185 0.0226 0.2279 0.075(12) Uiso 1 1 d DR . . . .
H4W H 0.0322 -0.0759 0.1812 0.070(11) Uiso 1 1 d DR . . . .
O8 O 0.2581(2) 0.1616(3) 0.29409(7) 0.0398(4) Uani 1 1 d D . . . .
H5W H 0.1857 0.1585 0.3147 0.055(9) Uiso 1 1 d DR . . . .
H6W H 0.3461 0.1738 0.3149 0.060(10) Uiso 1 1 d DR . . . .
C1 C 0.3065(3) -0.1419(3) -0.02660(10) 0.0313(5) Uani 1 1 d . . . . .
C2 C 0.2248(3) 0.0298(4) -0.04128(10) 0.0387(6) Uani 1 1 d . . . . .
H2 H 0.1950 0.0642 -0.0814 0.046 Uiso 1 1 calc R U . . .
C3 C 0.1868(3) 0.1518(4) 0.00422(10) 0.0348(5) Uani 1 1 d . . . . .
H3 H 0.1322 0.2690 -0.0056 0.042 Uiso 1 1 calc R U . . .
C4 C 0.2294(2) 0.1013(3) 0.06435(9) 0.0238(4) Uani 1 1 d . . . . .
C5 C 0.3130(2) -0.0749(3) 0.07991(9) 0.0234(4) Uani 1 1 d . . . . .
C6 C 0.3509(3) -0.1936(3) 0.03296(10) 0.0281(5) Uani 1 1 d . . . . .
H6 H 0.4072 -0.3100 0.0420 0.034 Uiso 1 1 calc R U . . .
C7 C 0.3705(3) -0.1528(3) 0.14257(10) 0.0247(4) Uani 1 1 d . . . . .
C8 C 0.1015(3) 0.4001(3) 0.09264(10) 0.0276(5) Uani 1 1 d . . . . .
H8A H 0.0031 0.3640 0.0677 0.033 Uiso 1 1 calc R U . . .
H8B H 0.1609 0.4853 0.0692 0.033 Uiso 1 1 calc R U . . .
C9 C 0.0643(3) 0.5110(3) 0.14764(10) 0.0261(4) Uani 1 1 d . . . . .
Br1 Br 0.36257(4) -0.30809(5) -0.08819(2) 0.05263(10) 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 0.0033 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'
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'
Br Br -0.2901 2.4595 '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
O2 Ni1 O5 167.95(6) . .
O2 Ni1 O8 96.26(7) . .
O5 Ni1 O8 95.78(7) . .
O2 Ni1 O6 90.14(7) . .
O5 Ni1 O6 89.70(7) . .
O8 Ni1 O6 90.47(7) . .
O2 Ni1 O7 90.46(7) . .
O5 Ni1 O7 89.30(7) . .
O8 Ni1 O7 91.48(7) . .
O6 Ni1 O7 177.89(7) . .
O2 Ni1 O3 87.49(6) . .
O5 Ni1 O3 80.46(6) . .
O8 Ni1 O3 176.22(7) . .
O6 Ni1 O3 89.99(6) . .
O7 Ni1 O3 88.01(6) . .
C7 O2 Ni1 133.65(14) . .
C4 O3 C8 118.20(16) . .
C4 O3 Ni1 129.62(12) . .
C8 O3 Ni1 111.92(12) . .
C9 O5 Ni1 116.99(13) . .
Ni1 O6 H1W 113.7 . .
Ni1 O6 H2W 123.0 . .
H1W O6 H2W 111.5 . .
Ni1 O7 H3W 113.1 . .
Ni1 O7 H4W 107.4 . .
H3W O7 H4W 110.8 . .
Ni1 O8 H5W 125.5 . .
Ni1 O8 H6W 121.8 . .
H5W O8 H6W 112.0 . .
C2 C1 C6 120.4(2) . .
C2 C1 Br1 119.97(17) . .
C6 C1 Br1 119.58(17) . .
C1 C2 C3 119.4(2) . .
C1 C2 H2 120.3 . .
C3 C2 H2 120.3 . .
C2 C3 C4 120.9(2) . .
C2 C3 H3 119.6 . .
C4 C3 H3 119.6 . .
O3 C4 C3 120.59(19) . .
O3 C4 C5 119.24(18) . .
C3 C4 C5 120.16(19) . .
C6 C5 C4 117.51(19) . .
C6 C5 C7 114.93(18) . .
C4 C5 C7 127.56(18) . .
C1 C6 C5 121.6(2) . .
C1 C6 H6 119.2 . .
C5 C6 H6 119.2 . .
O1 C7 O2 121.7(2) . .
O1 C7 C5 115.98(19) . .
O2 C7 C5 122.28(18) . .
O3 C8 C9 111.02(17) . .
O3 C8 H8A 109.4 . .
C9 C8 H8A 109.4 . .
O3 C8 H8B 109.4 . .
C9 C8 H8B 109.4 . .
H8A C8 H8B 108.0 . .
O4 C9 O5 125.6(2) . .
O4 C9 C8 114.81(19) . .
O5 C9 C8 119.56(19) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ni1 O2 1.9852(15) .
Ni1 O5 2.0175(15) .
Ni1 O8 2.0181(16) .
Ni1 O6 2.0538(16) .
Ni1 O7 2.0683(16) .
Ni1 O3 2.1067(15) .
O1 C7 1.254(3) .
O2 C7 1.258(3) .
O3 C4 1.387(2) .
O3 C8 1.438(2) .
O4 C9 1.245(3) .
O5 C9 1.258(3) .
O6 H1W 0.8215 .
O6 H2W 0.8264 .
O7 H3W 0.8334 .
O7 H4W 0.8222 .
O8 H5W 0.8221 .
O8 H6W 0.8287 .
C1 C2 1.370(3) .
C1 C6 1.382(3) .
C1 Br1 1.896(2) .
C2 C3 1.387(3) .
C2 H2 0.9300 .
C3 C4 1.390(3) .
C3 H3 0.9300 .
C4 C5 1.407(3) .
C5 C6 1.399(3) .
C5 C7 1.517(3) .
C6 H6 0.9300 .
C8 C9 1.516(3) .
C8 H8A 0.9700 .
C8 H8B 0.9700 .
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 2.59 3.312(3) 134.5 3_565
O8 H6W O1 0.83 1.87 2.694(2) 173.5 2_655
O8 H5W O4 0.82 1.96 2.782(2) 176.9 2_545
O7 H4W O4 0.82 2.02 2.807(2) 160.2 1_545
O7 H3W O5 0.83 1.99 2.809(2) 168.8 2_545
O6 H2W O2 0.83 2.00 2.804(2) 165.9 2_655
O6 H1W O1 0.82 1.95 2.759(2) 170.8 1_565
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 0.1(4) . . . .
Br1 C1 C2 C3 -178.9(2) . . . .
C1 C2 C3 C4 -0.6(4) . . . .
C8 O3 C4 C3 3.3(3) . . . .
Ni1 O3 C4 C3 176.96(17) . . . .
C8 O3 C4 C5 -177.63(19) . . . .
Ni1 O3 C4 C5 -4.0(3) . . . .
C2 C3 C4 O3 179.5(2) . . . .
C2 C3 C4 C5 0.4(4) . . . .
O3 C4 C5 C6 -178.82(19) . . . .
C3 C4 C5 C6 0.3(3) . . . .
O3 C4 C5 C7 0.3(3) . . . .
C3 C4 C5 C7 179.3(2) . . . .
C2 C1 C6 C5 0.6(4) . . . .
Br1 C1 C6 C5 179.60(17) . . . .
C4 C5 C6 C1 -0.8(3) . . . .
C7 C5 C6 C1 -180.0(2) . . . .
Ni1 O2 C7 O1 -179.22(16) . . . .
Ni1 O2 C7 C5 0.6(3) . . . .
C6 C5 C7 O1 0.5(3) . . . .
C4 C5 C7 O1 -178.6(2) . . . .
C6 C5 C7 O2 -179.3(2) . . . .
C4 C5 C7 O2 1.6(3) . . . .
C4 O3 C8 C9 176.91(18) . . . .
Ni1 O3 C8 C9 2.2(2) . . . .
Ni1 O5 C9 O4 179.54(17) . . . .
Ni1 O5 C9 C8 0.1(3) . . . .
O3 C8 C9 O4 178.92(18) . . . .
O3 C8 C9 O5 -1.6(3) . . . .
