#------------------------------------------------------------------------------
#$Date: 2024-10-13 03:55:40 +0300 (Sun, 13 Oct 2024) $
#$Revision: 295471 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/94/7249454.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_7249454
loop_
_publ_author_name
'Hosseinpoor, Saeed'
'Pourayoubi, Mehrdad'
'Zmeškalová, Eliška'
'Poupon, Morgane'
_publ_section_title
;
 Supramolecular motifs formed by CH3/Cl-substituted arene groups: evidence
 for structural differences in thiophosphoramides and similarities in
 their complexes
;
_journal_issue                   44
_journal_name_full               'RSC Advances'
_journal_page_first              32206
_journal_page_last               32220
_journal_paper_doi               10.1039/D4RA05281A
_journal_volume                  14
_journal_year                    2024
_chemical_formula_moiety         'C12 H17 Cl1 N2 Ni0.50 O2 P1 S2'
_chemical_formula_sum            'C12 H17 Cl N2 Ni0.5 O2 P S2'
_chemical_formula_weight         381.19
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     other
_audit_update_record
;
2023-12-04 deposited with the CCDC.	2024-09-26 downloaded from the CCDC.
;
_cell_angle_alpha                113.275(3)
_cell_angle_beta                 97.462(3)
_cell_angle_gamma                97.123(3)
_cell_formula_units_Z            2
_cell_length_a                   7.8502(2)
_cell_length_b                   10.1868(4)
_cell_length_c                   11.6914(4)
_cell_measurement_reflns_used    7760
_cell_measurement_temperature    120
_cell_measurement_theta_max      67.38
_cell_measurement_theta_min      4.18
_cell_volume                     835.66(5)
_computing_cell_refinement
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_data_reduction
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      120
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  'focussing mirrors'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.096
_diffrn_reflns_av_unetI/netI     0.078
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12744
_diffrn_reflns_theta_full        66.285
_diffrn_reflns_theta_max         67.581
_diffrn_reflns_theta_min         4.198
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.860
_exptl_absorpt_correction_T_max  0.49
_exptl_absorpt_correction_T_min  0.15
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.515
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             394
_exptl_crystal_size_max          0.312
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.123
_refine_diff_density_max         0.76
_refine_diff_density_min         -0.81
_refine_ls_extinction_coef       18(3)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   1.0003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         2996
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0496
_refine_ls_shift/su_max          0.0002613
_refine_ls_shift/su_mean         0.0000195
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.09P)² + 0.82P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1414
_refine_ls_wR_factor_gt          0.1338
_refine_ls_wR_factor_ref         0.1414
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              11
_reflns_limit_k_min              -12
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                2716
_reflns_number_total             2996
_reflns_threshold_expression     I>2.0σ(I)
_oxford_diffrn_Wilson_B_factor   2.08
_oxford_diffrn_Wilson_scale      0.02
_oxford_refine_ls_r_factor_ref   0.0534
_oxford_refine_ls_scale          8.7(6)
_oxford_reflns_number_all        2996
_cod_data_source_file            d4ra05281a2.cif
_cod_data_source_block           I_CCDC1
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 
;
_cod_original_sg_symbol_H-M      'P -1 '
_cod_original_formula_sum        'C12 H17 Cl1 N2 Ni0.50 O2 P1 S2'
_cod_database_code               7249454
_oxford_refine_reflns_threshold_expression I>-3.0\s(I)
_oxford_refine_ls_r_factor_all   0.0534
_oxford_refine_ls_wr_factor_all  0.1414
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
Ni1 Ni 0.0000 1.0000 0.5000 0.0186 1.0000 Uani S . . . . .
S2 S 0.16902(10) 0.83405(8) 0.47302(7) 0.0234 1.0000 Uani . . . . . .
C3 C 0.2431(4) 0.9231(3) 0.3850(3) 0.0201 1.0000 Uani . . . . . .
N4 N 0.1493(3) 1.0267(3) 0.3917(2) 0.0214 1.0000 Uani . . . . . .
P5 P 0.17478(10) 1.15490(8) 0.33955(7) 0.0219 1.0000 Uani . . . . . .
S6 S 0.33370(16) 1.13540(10) 0.22309(10) 0.0492 1.0000 Uani . . . . . .
O7 O -0.0145(3) 1.1689(2) 0.2892(2) 0.0277 1.0000 Uani . . . . . .
C8 C -0.1193(7) 1.0581(4) 0.1699(4) 0.0553 1.0000 Uani . . . . . .
C9 C -0.2434(7) 1.1197(7) 0.1170(5) 0.0829 1.0000 Uani . . . . . .
O10 O 0.2269(3) 1.2965(2) 0.46751(19) 0.0227 1.0000 Uani . . . . . .
C11 C 0.2399(5) 1.4405(3) 0.4687(3) 0.0289 1.0000 Uani . . . . . .
C12 C 0.2725(5) 1.5481(4) 0.6048(3) 0.0382 1.0000 Uani . . . . . .
N13 N 0.3717(3) 0.8928(3) 0.3228(2) 0.0249 1.0000 Uani . . . . . .
C14 C 0.4690(5) 0.7789(4) 0.3208(3) 0.0303 1.0000 Uani . . . . . .
C15 C 0.5633(4) 0.7347(3) 0.2107(3) 0.0214 1.0000 Uani . . . . . .
C16 C 0.4846(4) 0.7165(3) 0.0903(3) 0.0254 1.0000 Uani . . . . . .
C17 C 0.5731(4) 0.6722(4) -0.0102(3) 0.0278 1.0000 Uani . . . . . .
C18 C 0.7389(5) 0.6451(4) 0.0110(3) 0.0292 1.0000 Uani . . . . . .
Cl19 Cl 0.84798(16) 0.58485(14) -0.11521(10) 0.0580 1.0000 Uani . . . . . .
C20 C 0.8212(4) 0.6634(4) 0.1300(3) 0.0298 1.0000 Uani . . . . . .
C21 C 0.7323(4) 0.7084(3) 0.2295(3) 0.0242 1.0000 Uani . . . . . .
H81 H -0.0466 1.0147 0.1111 0.0655 1.0000 Uiso R . . . . .
H82 H -0.1829 0.9828 0.1859 0.0652 1.0000 Uiso R . . . . .
H91 H -0.3163 1.0478 0.0395 0.1257 1.0000 Uiso R . . . . .
H92 H -0.1780 1.1935 0.1000 0.1267 1.0000 Uiso R . . . . .
H93 H -0.3137 1.1640 0.1757 0.1262 1.0000 Uiso R . . . . .
H111 H 0.3380 1.4555 0.4292 0.0348 1.0000 Uiso R . . . . .
H112 H 0.1312 1.4442 0.4213 0.0347 1.0000 Uiso R . . . . .
H121 H 0.2863 1.6458 0.6089 0.0559 1.0000 Uiso R . . . . .
H122 H 0.3776 1.5403 0.6514 0.0558 1.0000 Uiso R . . . . .
H123 H 0.1746 1.5281 0.6426 0.0561 1.0000 Uiso R . . . . .
H142 H 0.5538 0.8140 0.3995 0.0359 1.0000 Uiso R . . . . .
H141 H 0.3853 0.6954 0.3138 0.0356 1.0000 Uiso R . . . . .
H161 H 0.3703 0.7347 0.0759 0.0303 1.0000 Uiso R . . . . .
H171 H 0.5213 0.6601 -0.0924 0.0335 1.0000 Uiso R . . . . .
H201 H 0.9351 0.6465 0.1442 0.0363 1.0000 Uiso R . . . . .
H211 H 0.7876 0.7203 0.3106 0.0286 1.0000 Uiso R . . . . .
H131 H 0.4047 0.9473 0.2843 0.0293 1.0000 Uiso R . . . . .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
S 0.3331 0.5567 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720 0.8669
'International Tables Vol C 4.2.6.8 and 6.1.1.4'
P 0.2955 0.4335 6.4345 1.9067 4.1791 27.1570 1.7800 0.5260 1.4908 68.1645 1.1149
'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508
'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Cl 0.3639 0.7018 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784
-9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Ni -3.0029 0.5091 12.8376 3.8785 7.2920 0.2565 4.4438 12.1763 2.3800 66.3421
1.0341 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C3 2_576 Ni1 . N4 2_576 31.96(10) yes
C3 2_576 Ni1 . S2 2_576 42.32(7) yes
N4 2_576 Ni1 . S2 2_576 74.27(7) yes
C3 2_576 Ni1 . P5 2_576 54.97(7) yes
N4 2_576 Ni1 . P5 2_576 23.15(7) yes
S2 2_576 Ni1 . P5 2_576 97.25(2) yes
C3 2_576 Ni1 . S2 . 137.68(7) yes
N4 2_576 Ni1 . S2 . 105.73(7) yes
S2 2_576 Ni1 . S2 . 179.99 yes
P5 2_576 Ni1 . S2 . 82.75(2) yes
C3 2_576 Ni1 . C3 . 180.00 yes
N4 2_576 Ni1 . C3 . 148.04(10) yes
S2 2_576 Ni1 . C3 . 137.68(7) yes
P5 2_576 Ni1 . C3 . 125.03(7) yes
S2 . Ni1 . C3 . 42.32(7) yes
C3 2_576 Ni1 . N4 . 148.04(10) yes
N4 2_576 Ni1 . N4 . 179.99 yes
S2 2_576 Ni1 . N4 . 105.73(7) yes
P5 2_576 Ni1 . N4 . 156.85(7) yes
S2 . Ni1 . N4 . 74.27(7) yes
C3 2_576 Ni1 . P5 . 125.03(7) yes
N4 2_576 Ni1 . P5 . 156.85(7) yes
S2 2_576 Ni1 . P5 . 82.75(2) yes
P5 2_576 Ni1 . P5 . 180.00 yes
S2 . Ni1 . P5 . 97.25(2) yes
C3 . Ni1 . N4 . 31.96(10) yes
C3 . Ni1 . P5 . 54.97(7) yes
N4 . Ni1 . P5 . 23.15(7) yes
Ni1 . S2 . C3 . 77.41(10) yes
Ni1 . C3 . S2 . 60.27(9) yes
Ni1 . C3 . N4 . 48.68(14) yes
S2 . C3 . N4 . 108.9(2) yes
Ni1 . C3 . N13 . 175.1(2) yes
S2 . C3 . N13 . 124.5(2) yes
N4 . C3 . N13 . 126.5(3) yes
C3 . N4 . Ni1 . 99.36(18) yes
C3 . N4 . P5 . 130.3(2) yes
Ni1 . N4 . P5 . 129.79(14) yes
N4 . P5 . Ni1 . 27.06(9) yes
N4 . P5 . S6 . 116.30(10) yes
Ni1 . P5 . S6 . 143.30(4) yes
N4 . P5 . O7 . 106.19(13) yes
Ni1 . P5 . O7 . 87.43(9) yes
S6 . P5 . O7 . 114.85(10) yes
N4 . P5 . O10 . 101.61(12) yes
Ni1 . P5 . O10 . 86.33(8) yes
S6 . P5 . O10 . 115.35(10) yes
O7 . P5 . O10 . 100.56(11) yes
P5 . O7 . C8 . 120.8(3) yes
O7 . C8 . C9 . 110.1(3) yes
O7 . C8 . H81 . 111.1 no
C9 . C8 . H81 . 110.8 no
O7 . C8 . H82 . 109.2 no
C9 . C8 . H82 . 107.7 no
H81 . C8 . H82 . 107.9 no
C8 . C9 . H91 . 111.5 no
C8 . C9 . H92 . 106.8 no
H91 . C9 . H92 . 109.5 no
C8 . C9 . H93 . 110.8 no
H91 . C9 . H93 . 109.9 no
H92 . C9 . H93 . 108.4 no
P5 . O10 . C11 . 121.39(18) yes
O10 . C11 . C12 . 107.2(3) yes
O10 . C11 . H111 . 107.5 no
C12 . C11 . H111 . 110.8 no
O10 . C11 . H112 . 108.4 no
C12 . C11 . H112 . 111.5 no
H111 . C11 . H112 . 111.1 no
C11 . C12 . H121 . 109.2 no
C11 . C12 . H122 . 110.7 no
H121 . C12 . H122 . 108.2 no
C11 . C12 . H123 . 109.0 no
H121 . C12 . H123 . 111.0 no
H122 . C12 . H123 . 108.7 no
C3 . N13 . C14 . 123.4(3) yes
C3 . N13 . H131 . 118.2 no
C14 . N13 . H131 . 118.3 no
N13 . C14 . C15 . 111.4(3) yes
N13 . C14 . H142 . 109.4 no
C15 . C14 . H142 . 109.2 no
N13 . C14 . H141 . 107.7 no
C15 . C14 . H141 . 110.1 no
H142 . C14 . H141 . 109.2 no
C14 . C15 . C16 . 121.8(3) yes
C14 . C15 . C21 . 119.1(3) yes
C16 . C15 . C21 . 119.1(3) yes
C15 . C16 . C17 . 120.6(3) yes
C15 . C16 . H161 . 120.3 no
C17 . C16 . H161 . 119.1 no
C16 . C17 . C18 . 119.0(3) yes
C16 . C17 . H171 . 121.4 no
C18 . C17 . H171 . 119.6 no
C17 . C18 . Cl19 . 119.2(3) yes
C17 . C18 . C20 . 121.8(3) yes
Cl19 . C18 . C20 . 119.0(2) yes
C18 . C20 . C21 . 118.7(3) yes
C18 . C20 . H201 . 121.3 no
C21 . C20 . H201 . 119.9 no
C15 . C21 . C20 . 120.8(3) yes
C15 . C21 . H211 . 120.2 no
C20 . C21 . H211 . 119.0 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Ni1 . C3 2_576 2.503(3) yes
Ni1 . N4 2_576 1.906(2) yes
Ni1 . S2 2_576 2.2274(7) yes
Ni1 . P5 2_576 3.2190(7) yes
Ni1 . S2 . 2.2274(7) yes
Ni1 . C3 . 2.503(3) yes
Ni1 . N4 . 1.906(2) yes
Ni1 . P5 . 3.2190(7) yes
S2 . C3 . 1.727(3) yes
C3 . N4 . 1.343(4) yes
C3 . N13 . 1.317(4) yes
N4 . P5 . 1.647(2) yes
P5 . S6 . 1.9336(11) yes
P5 . O7 . 1.571(2) yes
P5 . O10 . 1.573(2) yes
O7 . C8 . 1.457(4) yes
C8 . C9 . 1.423(7) yes
C8 . H81 . 0.958 no
C8 . H82 . 0.957 no
C9 . H91 . 0.960 no
C9 . H92 . 0.958 no
C9 . H93 . 0.946 no
O10 . C11 . 1.452(4) yes
C11 . C12 . 1.498(5) yes
C11 . H111 . 0.974 no
C11 . H112 . 0.968 no
C12 . H121 . 0.969 no
C12 . H122 . 0.958 no
C12 . H123 . 0.974 no
N13 . C14 . 1.460(4) yes
N13 . H131 . 0.877 no
C14 . C15 . 1.510(4) yes
C14 . H142 . 0.969 no
C14 . H141 . 0.977 no
C15 . C16 . 1.391(4) yes
C15 . C21 . 1.392(4) yes
C16 . C17 . 1.392(4) yes
C16 . H161 . 0.946 no
C17 . C18 . 1.375(5) yes
C17 . H171 . 0.947 no
C18 . Cl19 . 1.741(3) yes
C18 . C20 . 1.386(5) yes
C20 . C21 . 1.385(5) yes
C20 . H201 . 0.937 no
C21 . H211 . 0.944 no
