#------------------------------------------------------------------------------
#$Date: 2023-12-07 13:49:50 +0200 (Thu, 07 Dec 2023) $
#$Revision: 288137 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/29/2022926.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2022926
loop_
_publ_author_name
'Suyunov, Jabbor R.'
'Turaev, Khayit Kh'
'Alimnazarov, Bekmurod Kh'
'Nazarov, Yusuf E.'
'Mengnorov, Islombek J.'
'Ibragimov, Bakhtiyar T.'
'Ashurov, Jamshid M.'
_publ_section_title
;
 Synthesis, crystal structure and Hirshfeld surface analysis of
 di-aqua-bis-(o-phenyl-enedi-amine-κ²N,N')nickel(II)
 naphthalene-1,5-di-sulfonate.
;
_journal_coeditor_code           WM5701
_journal_issue                   'Pt 11'
_journal_name_full
'Acta crystallographica. Section E, Crystallographic communications'
_journal_page_first              1083
_journal_page_last               1087
_journal_paper_doi               10.1107/S2056989023009350
_journal_volume                  79
_journal_year                    2023
_chemical_formula_iupac          '[Ni (C6 H8 N2)2 (H2 O1)2] (C10 H6 O6 S2)'
_chemical_formula_moiety         'C12 H20 N4 Ni O2 2+, C10 H6 O6 S2 2-'
_chemical_formula_sum            'C22 H26 N4 Ni O8 S2'
_chemical_formula_weight         597.30
_chemical_name_systematic
;
Diaquabis(o-phenylenediamine-κ²N,N')nickel(II)
naphthalene-1,5-disulfonate
;
_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
_atom_sites_solution_primary     iterative
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_cell_angle_alpha                90
_cell_angle_beta                 111.554(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.7613(3)
_cell_length_b                   7.70540(10)
_cell_length_c                   13.4641(3)
_cell_measurement_reflns_used    6737
_cell_measurement_temperature    563.15
_cell_measurement_theta_max      71.0430
_cell_measurement_theta_min      4.0690
_cell_volume                     1231.36(5)
_computing_cell_refinement
;
CrysAlisPro (Rigaku OD, 2023)
;
_computing_data_collection
;
CrysAlisPro (Rigaku OD, 2023)
;
_computing_data_reduction
;
CrysAlisPro (Rigaku OD, 2023)
;
_computing_molecular_graphics
;
Olex2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
Olex2 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
SHELXL (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      563.15
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11384
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.257
_diffrn_reflns_theta_min         4.083
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    3.219
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57293
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2023)
;
_exptl_crystal_colour            'light green'
_exptl_crystal_density_diffrn    1.611
_exptl_crystal_description       block
_exptl_crystal_F_000             620
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.502
_refine_diff_density_min         -0.488
_refine_ls_extinction_coef       0.0006(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL (Sheldrick, 2015a)
;
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         2380
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0360
_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)+(0.0480P)²+0.8302P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0948
_refine_ls_wR_factor_ref         0.0971
_reflns_number_gt                2152
_reflns_number_total             2380
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            wm5701sup1.cif
_cod_data_source_block           I
_cod_depositor_comments          'Adding full bibliography for 2022926.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2022926
_cod_database_fobs_code          2022926
_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   0.538
_shelx_estimated_absorpt_t_max   0.661
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni Ni1 1.000000 0.500000 0.500000 0.02713(17) Uani d 1 . .
S S1 0.69836(5) 0.87424(8) 0.39745(4) 0.03779(18) Uani d 1 . .
O O1W 0.83329(14) 0.4677(2) 0.38469(14) 0.0412(4) Uani d 1 . .
O O1 0.73435(15) 0.7254(2) 0.46852(14) 0.0488(5) Uani d 1 . .
N N1 0.99045(16) 0.2387(2) 0.53808(16) 0.0330(4) Uani d 1 . .
O O3 0.62288(17) 0.8217(3) 0.29283(14) 0.0574(5) Uani d 1 . .
N N2 0.93181(15) 0.5408(2) 0.61643(14) 0.0298(4) Uani d 1 . .
O O2 0.79217(17) 0.9758(3) 0.39332(19) 0.0636(6) Uani d 1 . .
C C11 0.47191(16) 1.0579(3) 0.52339(16) 0.0276(4) Uani d 1 . .
C C6 0.91414(17) 0.3765(3) 0.66003(16) 0.0297(4) Uani d 1 . .
C C1 0.94563(18) 0.2253(3) 0.62287(17) 0.0319(5) Uani d 1 . .
C C7 0.62041(18) 1.0098(3) 0.45202(17) 0.0313(5) Uani d 1 . .
C C10 0.50918(19) 1.2316(3) 0.54324(18) 0.0350(5) Uani d 1 . .
H H10 0.473811 1.306841 0.575033 0.042 Uiso calc 1 . .
C C5 0.86718(19) 0.3671(3) 0.73833(18) 0.0381(5) Uani d 1 . .
H H5 0.846130 0.468202 0.763862 0.046 Uiso calc 1 . .
C C8 0.65220(18) 1.1796(3) 0.47028(19) 0.0385(5) Uani d 1 . .
H H8 0.711068 1.221455 0.451995 0.046 Uiso calc 1 . .
C C9 0.5960(2) 1.2909(3) 0.5166(2) 0.0405(5) Uani d 1 . .
H H9 0.618250 1.406318 0.529312 0.049 Uiso calc 1 . .
C C2 0.9316(2) 0.0661(3) 0.6643(2) 0.0446(6) Uani d 1 . .
H H2 0.953980 -0.035050 0.639981 0.054 Uiso calc 1 . .
C C4 0.8518(2) 0.2078(4) 0.7781(2) 0.0474(6) Uani d 1 . .
H H4 0.819333 0.201834 0.829604 0.057 Uiso calc 1 . .
C C3 0.8845(2) 0.0572(4) 0.7417(2) 0.0510(6) Uani d 1 . .
H H3 0.874888 -0.049782 0.769179 0.061 Uiso calc 1 . .
H H2A 0.8674(14) 0.596(3) 0.585(2) 0.049(8) Uiso d 1 . .
H H2B 0.9775(17) 0.607(3) 0.6689(15) 0.038(7) Uiso d 1 . .
H H1A 0.946(2) 0.188(4) 0.4786(15) 0.062(9) Uiso d 1 . .
H H1B 1.0556(14) 0.182(3) 0.561(2) 0.052(8) Uiso d 1 . .
H H1WA 0.822(3) 0.447(5) 0.3199(11) 0.072(11) Uiso d 1 . .
H H1WB 0.787(2) 0.546(4) 0.386(3) 0.085(12) Uiso d 1 . .
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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni -3.0029 0.5091 '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'
S S 0.3331 0.5567 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1W Ni1 O1W . 3_766 180.0 ?
N1 Ni1 O1W 3_766 3_766 86.20(8) ?
N1 Ni1 O1W 3_766 . 93.80(8) ?
N1 Ni1 O1W . 3_766 93.80(8) ?
N1 Ni1 O1W . . 86.20(8) ?
N1 Ni1 N1 . 3_766 180.0 ?
N2 Ni1 O1W 3_766 . 90.88(7) ?
N2 Ni1 O1W 3_766 3_766 89.12(7) ?
N2 Ni1 O1W . . 89.12(7) ?
N2 Ni1 O1W . 3_766 90.88(7) ?
N2 Ni1 N1 3_766 3_766 83.26(7) ?
N2 Ni1 N1 . 3_766 96.74(7) ?
N2 Ni1 N1 . . 83.26(7) ?
N2 Ni1 N1 3_766 . 96.74(7) ?
N2 Ni1 N2 . 3_766 180.00(10) ?
O1 S1 C7 . . 106.30(10) ?
O3 S1 O1 . . 110.91(13) ?
O3 S1 O2 . . 112.29(13) ?
O3 S1 C7 . . 107.13(10) ?
O2 S1 O1 . . 112.67(12) ?
O2 S1 C7 . . 107.12(11) ?
Ni1 O1W H1WA . . 121(2) ?
Ni1 O1W H1WB . . 115(3) ?
H1WA O1W H1WB . . 107(3) ?
Ni1 N1 H1A . . 106(2) ?
Ni1 N1 H1B . . 115(2) ?
C1 N1 Ni1 . . 109.60(13) ?
C1 N1 H1A . . 112(2) ?
C1 N1 H1B . . 106.1(19) ?
H1A N1 H1B . . 108(3) ?
Ni1 N2 H2A . . 107.0(18) ?
Ni1 N2 H2B . . 110.6(16) ?
C6 N2 Ni1 . . 110.14(13) ?
C6 N2 H2A . . 110.8(19) ?
C6 N2 H2B . . 109.3(17) ?
H2A N2 H2B . . 109(3) ?
C11 C11 C7 3_676 3_676 117.6(2) ?
C10 C11 C11 . 3_676 119.1(2) ?
C10 C11 C7 . 3_676 123.28(19) ?
C1 C6 N2 . . 118.72(18) ?
C1 C6 C5 . . 119.5(2) ?
C5 C6 N2 . . 121.8(2) ?
C6 C1 N1 . . 118.23(19) ?
C6 C1 C2 . . 120.1(2) ?
C2 C1 N1 . . 121.6(2) ?
C11 C7 S1 3_676 . 120.95(16) ?
C8 C7 S1 . . 117.60(17) ?
C8 C7 C11 . 3_676 121.45(19) ?
C11 C10 H10 . . 119.4 ?
C9 C10 C11 . . 121.2(2) ?
C9 C10 H10 . . 119.4 ?
C6 C5 H5 . . 119.9 ?
C4 C5 C6 . . 120.1(2) ?
C4 C5 H5 . . 119.9 ?
C7 C8 H8 . . 120.0 ?
C7 C8 C9 . . 120.0(2) ?
C9 C8 H8 . . 120.0 ?
C10 C9 C8 . . 120.7(2) ?
C10 C9 H9 . . 119.7 ?
C8 C9 H9 . . 119.7 ?
C1 C2 H2 . . 119.9 ?
C3 C2 C1 . . 120.2(2) ?
C3 C2 H2 . . 119.9 ?
C5 C4 H4 . . 119.9 ?
C5 C4 C3 . . 120.2(2) ?
C3 C4 H4 . . 119.9 ?
C2 C3 H3 . . 120.1 ?
C4 C3 C2 . . 119.8(2) ?
C4 C3 H3 . . 120.1 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Ni1 O1W 3_766 2.1381(17) ?
Ni1 O1W . 2.1381(17) ?
Ni1 N1 . 2.0924(18) ?
Ni1 N1 3_766 2.0924(18) ?
Ni1 N2 3_766 2.0776(17) ?
Ni1 N2 . 2.0775(17) ?
S1 O1 . 1.4558(18) ?
S1 O3 . 1.4419(19) ?
S1 O2 . 1.448(2) ?
S1 C7 . 1.777(2) ?
O1W H1WA . 0.846(10) ?
O1W H1WB . 0.850(10) ?
N1 C1 . 1.456(3) ?
N1 H1A . 0.886(10) ?
N1 H1B . 0.889(10) ?
N2 C6 . 1.447(3) ?
N2 H2A . 0.882(10) ?
N2 H2B . 0.891(10) ?
C11 C11 3_676 1.427(4) ?
C11 C7 3_676 1.434(3) ?
C11 C10 . 1.413(3) ?
C6 C1 . 1.385(3) ?
C6 C5 . 1.393(3) ?
C1 C2 . 1.386(3) ?
C7 C8 . 1.365(3) ?
C10 H10 . 0.9300 ?
C10 C9 . 1.363(3) ?
C5 H5 . 0.9300 ?
C5 C4 . 1.382(4) ?
C8 H8 . 0.9300 ?
C8 C9 . 1.403(3) ?
C9 H9 . 0.9300 ?
C2 H2 . 0.9300 ?
C2 C3 . 1.383(4) ?
C4 H4 . 0.9300 ?
C4 C3 . 1.383(4) ?
C3 H3 . 0.9300 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1A O2 1_545 0.886(10) 2.484(19) 3.268(3) 148(3) yes
N1 H1B O2 3_766 0.889(10) 2.179(11) 3.066(3) 175(3) yes
N2 H2A O1 . 0.882(10) 2.096(14) 2.941(2) 160(3) yes
N2 H2B O3 4_676 0.891(10) 2.063(13) 2.908(3) 158(2) yes
O1W H1WA O3 2_645 0.846(10) 2.12(2) 2.876(3) 148(3) yes
O1W H1WB O1 . 0.850(10) 2.04(2) 2.803(2) 150(3) yes
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
Ni1 N1 C1 C6 . . . . 2.3(2) ?
Ni1 N1 C1 C2 . . . . -179.29(18) ?
Ni1 N2 C6 C1 . . . . 1.6(2) ?
Ni1 N2 C6 C5 . . . . -178.80(17) ?
S1 C7 C8 C9 . . . . -177.84(18) ?
O1 S1 C7 C11 . . . 3_676 -53.0(2) ?
O1 S1 C7 C8 . . . . 126.48(19) ?
N1 C1 C2 C3 . . . . -177.3(2) ?
O3 S1 C7 C11 . . . 3_676 65.6(2) ?
O3 S1 C7 C8 . . . . -114.9(2) ?
N2 C6 C1 N1 . . . . -2.7(3) ?
N2 C6 C1 C2 . . . . 178.9(2) ?
N2 C6 C5 C4 . . . . -179.9(2) ?
O2 S1 C7 C11 . . . 3_676 -173.73(18) ?
O2 S1 C7 C8 . . . . 5.8(2) ?
C11 C11 C10 C9 3_676 . . . 1.3(4) ?
C11 C7 C8 C9 3_676 . . . 1.7(3) ?
C11 C10 C9 C8 . . . . -1.1(4) ?
C6 C1 C2 C3 . . . . 1.0(4) ?
C6 C5 C4 C3 . . . . 1.0(4) ?
C1 C6 C5 C4 . . . . -0.3(3) ?
C1 C2 C3 C4 . . . . -0.3(4) ?
C7 C11 C10 C9 3_676 . . . -178.7(2) ?
C7 C8 C9 C10 . . . . -0.4(4) ?
C5 C6 C1 N1 . . . . 177.67(19) ?
C5 C6 C1 C2 . . . . -0.8(3) ?
C5 C4 C3 C2 . . . . -0.7(4) ?
