#------------------------------------------------------------------------------
#$Date: 2025-08-22 16:55:42 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301864 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/49/7214963.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_7214963
loop_
_publ_author_name
'Tan, Yu-Hui'
'Wu, Jin-Ji'
'Zhou, Hai-Yun'
'Yang, Li-Fei'
'Ye, Bao-Hui'
_publ_section_title
;
 Anion and pH induced spontaneous resolution of Δ- and Λ-[M(H2Biim)3]SO4
 (M = Ru2+, Co2+, Ni2+, Mn2+, Fe2+, and Zn2+) enantiomers
;
_journal_issue                   23
_journal_name_full               CrystEngComm
_journal_page_first              8117
_journal_paper_doi               10.1039/c2ce26334c
_journal_volume                  14
_journal_year                    2012
_chemical_formula_sum            'C18 H18 N12 Ni O4 S'
_chemical_formula_weight         557.21
_space_group_IT_number           80
_symmetry_space_group_name_Hall  'I 4bw'
_symmetry_space_group_name_H-M   'I 41'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.6811(4)
_cell_length_b                   12.6811(4)
_cell_length_c                   14.2077(8)
_cell_measurement_temperature    153(2)
_cell_volume                     2284.74(16)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_sigmaI/netI    0.0407
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3510
_diffrn_reflns_theta_full        62.51
_diffrn_reflns_theta_max         62.51
_diffrn_reflns_theta_min         4.67
_exptl_absorpt_coefficient_mu    2.565
_exptl_absorpt_correction_T_max  0.6279
_exptl_absorpt_correction_T_min  0.6279
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_density_diffrn    1.620
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1144
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         1636
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0339
_refine_ls_R_factor_gt           0.0298
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0390P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0703
_refine_ls_wR_factor_ref         0.0741
_reflns_number_gt                1533
_reflns_number_total             1636
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ce26334c.txt
_cod_data_source_block           ybh-tyh512-2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_hydrogen_treatment' value 'contr' was replaced with the
value 'constr' as specified in the replacement file
'src/cod-tools/trunk/data/replacement-values/replacement_values.lst'.

Automatic conversion script
Id: cif_fix_values 5376 2017-05-30 11:51:03Z andrius 
;
_cod_original_sg_symbol_H-M      I4(1)
_cod_database_code               7214963
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-y, x+1/2, z+1/4'
'y+1/2, -x, z+3/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1, z+1'
'-y+1/2, x+1, z+3/4'
'y+1, -x+1/2, z+5/4'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Ni1 Ni 0.0000 0.0000 0.01688(4) 0.0230(2) Uani 1 2 d S
C1 C 0.0528(2) -0.0222(2) 0.2137(2) 0.0236(6) Uani 1 1 d .
C2 C 0.2126(2) -0.0722(3) 0.2470(2) 0.0307(7) Uani 1 1 d .
H2 H 0.2742 -0.0892 0.2791 0.037 Uiso 1 1 calc R
C3 C 0.1961(2) -0.0784(3) 0.1525(2) 0.0295(7) Uani 1 1 d .
H3 H 0.2460 -0.1001 0.1085 0.035 Uiso 1 1 calc R
C4 C -0.1695(3) 0.0798(3) -0.1437(2) 0.0283(7) Uani 1 1 d .
H4 H -0.2186 0.0253 -0.1435 0.034 Uiso 1 1 calc R
N4 N -0.0850(2) 0.2248(2) -0.17943(18) 0.0252(6) Uani 1 1 d .
H4A H -0.0666 0.2831 -0.2056 0.030 Uiso 1 1 calc R
C6 C -0.0347(2) 0.1754(2) -0.1090(2) 0.0220(6) Uani 1 1 d .
C7 C 0.0597(2) 0.2036(2) -0.0583(2) 0.0222(6) Uani 1 1 d .
C8 C 0.1863(2) 0.1807(3) 0.0401(2) 0.0303(7) Uani 1 1 d .
H8 H 0.2302 0.1505 0.0850 0.036 Uiso 1 1 calc R
C9 C 0.2003(2) 0.2770(3) 0.0000(2) 0.0307(7) Uani 1 1 d .
H9 H 0.2548 0.3240 0.0125 0.037 Uiso 1 1 calc R
N1 N 0.0950(2) -0.0479(2) 0.13188(19) 0.0259(5) Uani 1 1 d .
N2 N 0.1205(2) -0.0360(2) 0.28530(19) 0.0279(6) Uani 1 1 d .
H2A H 0.1083 -0.0243 0.3439 0.033 Uiso 1 1 calc R
N3 N -0.0843(2) 0.0865(2) -0.08532(18) 0.0247(6) Uani 1 1 d .
C5 C -0.1718(3) 0.1643(3) -0.2020(2) 0.0299(7) Uani 1 1 d .
H5 H -0.2219 0.1787 -0.2480 0.036 Uiso 1 1 calc R
N5 N 0.0969(2) 0.1349(2) 0.00356(18) 0.0265(6) Uani 1 1 d .
N6 N 0.1190(2) 0.2918(2) -0.06219(19) 0.0252(6) Uani 1 1 d .
H6 H 0.1081 0.3464 -0.0968 0.030 Uiso 1 1 calc R
O1 O -0.02383(18) 0.40756(16) 0.72852(15) 0.0324(5) Uani 1 1 d .
O2 O 0.0915(2) 0.4771(2) 0.84778(19) 0.0452(7) Uani 1 1 d .
S1 S 0.0000 0.5000 0.78913(7) 0.0266(3) Uani 1 2 d S
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'
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'
Ni Ni -3.0029 0.5091 '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
N3 Ni1 N3 93.06(14) 6_444 .
N3 Ni1 N5 79.18(10) 6_444 6_444
N3 Ni1 N5 93.70(10) . 6_444
N3 Ni1 N5 93.70(10) 6_444 .
N3 Ni1 N5 79.18(10) . .
N5 Ni1 N5 169.74(14) 6_444 .
N3 Ni1 N1 95.36(10) 6_444 .
N3 Ni1 N1 165.36(10) . .
N5 Ni1 N1 99.63(10) 6_444 .
N5 Ni1 N1 88.32(10) . .
N3 Ni1 N1 165.36(10) 6_444 6_444
N3 Ni1 N1 95.36(10) . 6_444
N5 Ni1 N1 88.32(10) 6_444 6_444
N5 Ni1 N1 99.63(10) . 6_444
N1 Ni1 N1 79.10(14) . 6_444
N1 C1 N2 112.1(3) . .
N1 C1 C1 117.98(18) . 6_444
N2 C1 C1 129.75(18) . 6_444
C3 C2 N2 106.3(3) . .
C2 C3 N1 109.7(3) . .
C5 C4 N3 109.8(3) . .
C6 N4 C5 107.0(3) . .
N3 C6 N4 111.1(3) . .
N3 C6 C7 118.3(3) . .
N4 C6 C7 130.6(3) . .
N5 C7 N6 112.0(3) . .
N5 C7 C6 117.7(3) . .
N6 C7 C6 130.4(3) . .
C9 C8 N5 109.2(3) . .
C8 C9 N6 107.2(3) . .
C1 N1 C3 105.1(3) . .
C1 N1 Ni1 112.2(2) . .
C3 N1 Ni1 141.0(2) . .
C1 N2 C2 106.7(3) . .
C6 N3 C4 105.8(3) . .
C6 N3 Ni1 112.0(2) . .
C4 N3 Ni1 141.8(2) . .
C4 C5 N4 106.3(3) . .
C7 N5 C8 105.4(3) . .
C7 N5 Ni1 112.6(2) . .
C8 N5 Ni1 141.9(2) . .
C7 N6 C9 106.2(3) . .
O2 S1 O2 110.3(2) . 6_454
O2 S1 O1 109.63(14) . .
O2 S1 O1 109.08(13) 6_454 .
O2 S1 O1 109.08(13) . 6_454
O2 S1 O1 109.63(14) 6_454 6_454
O1 S1 O1 109.15(18) . 6_454
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ni1 N3 2.111(3) 6_444
Ni1 N3 2.111(3) .
Ni1 N5 2.115(3) 6_444
Ni1 N5 2.115(3) .
Ni1 N1 2.119(3) .
Ni1 N1 2.119(3) 6_444
C1 N1 1.320(4) .
C1 N2 1.343(4) .
C1 C1 1.453(6) 6_444
C2 C3 1.361(5) .
C2 N2 1.368(4) .
C3 N1 1.371(4) .
C4 C5 1.355(5) .
C4 N3 1.364(4) .
N4 C6 1.341(4) .
N4 C5 1.379(4) .
C6 N3 1.334(4) .
C6 C7 1.443(4) .
C7 N5 1.324(4) .
C7 N6 1.349(4) .
C8 C9 1.359(5) .
C8 N5 1.375(4) .
C9 N6 1.370(4) .
O1 S1 1.486(2) .
O2 S1 1.457(2) .
S1 O2 1.457(2) 6_454
S1 O1 1.486(2) 6_454
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139198331
