#------------------------------------------------------------------------------
#$Date: 2024-10-13 03:55:40 +0300 (Sun, 13 Oct 2024) $
#$Revision: 295471 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/94/7249453.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_7249453
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 H18 Cl1 N2 O2 P1 S2'
_chemical_formula_sum            'C12 H18 Cl N2 O2 P S2'
_chemical_formula_weight         352.85
_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                94.2128(19)
_cell_angle_beta                 99.531(2)
_cell_angle_gamma                98.0165(16)
_cell_formula_units_Z            2
_cell_length_a                   7.62900(10)
_cell_length_b                   7.67020(10)
_cell_length_c                   14.1025(4)
_cell_measurement_reflns_used    9497
_cell_measurement_temperature    95
_cell_measurement_theta_max      73.95
_cell_measurement_theta_min      3.17
_cell_volume                     801.93(3)
_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      95
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.981
_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  0.023
_diffrn_reflns_av_unetI/netI     0.026
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11539
_diffrn_reflns_theta_full        68.291
_diffrn_reflns_theta_max         74.111
_diffrn_reflns_theta_min         3.193
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.513
_exptl_absorpt_correction_T_max  0.46
_exptl_absorpt_correction_T_min  0.11
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.491
_exptl_crystal_size_mid          0.273
_exptl_crystal_size_min          0.142
_refine_diff_density_max         0.54
_refine_diff_density_min         -0.28
_refine_ls_extinction_coef       19.4(18)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   0.9743
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0258
_refine_ls_R_factor_gt           0.0255
_refine_ls_shift/su_max          0.0012674
_refine_ls_shift/su_mean         0.0000347
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.04P)² + 0.56P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0713
_refine_ls_wR_factor_gt          0.0710
_refine_ls_wR_factor_ref         0.0713
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              9
_reflns_limit_k_min              -9
_reflns_limit_l_max              17
_reflns_limit_l_min              0
_reflns_number_gt                3153
_reflns_number_total             3210
_reflns_threshold_expression     I>2.0σ(I)
_oxford_diffrn_Wilson_B_factor   1.02
_oxford_diffrn_Wilson_scale      0.01
_oxford_refine_ls_r_factor_ref   0.0258
_oxford_refine_ls_scale          9.3(3)
_oxford_reflns_number_all        3209
_cod_data_source_file            d4ra05281a2.cif
_cod_data_source_block           I
_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 H18 Cl1 N2 O2 P1 S2'
_cod_database_code               7249453
_oxford_refine_reflns_threshold_expression I>-3.0\s(I)
_oxford_refine_ls_r_factor_all   0.0258
_oxford_refine_ls_wr_factor_all  0.0713
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
Cl1 Cl 0.24735(5) 1.28829(4) 0.50474(3) 0.0198 1.0000 Uani . . . . . .
C2 C 0.27963(19) 1.08760(18) 0.44798(11) 0.0145 1.0000 Uani . . . . . .
C3 C 0.38225(19) 1.08873(19) 0.37592(12) 0.0177 1.0000 Uani . . . . . .
C4 C 0.40857(19) 0.92795(19) 0.33245(11) 0.0162 1.0000 Uani . . . . . .
C5 C 0.33268(18) 0.76853(18) 0.35998(10) 0.0119 1.0000 Uani . . . . . .
C6 C 0.36359(18) 0.59393(18) 0.31329(10) 0.0130 1.0000 Uani . . . . . .
N7 N 0.19678(15) 0.48619(15) 0.26148(9) 0.0124 1.0000 Uani . . . . . .
C8 C 0.12520(18) 0.50070(17) 0.17000(10) 0.0108 1.0000 Uani . . . . . .
S9 S 0.22448(4) 0.63808(4) 0.10002(2) 0.0143 1.0000 Uani . . . . . .
N10 N -0.03680(15) 0.39582(15) 0.13270(8) 0.0111 1.0000 Uani . . . . . .
P11 P -0.15977(4) 0.24630(4) 0.18524(3) 0.0109 1.0000 Uani . . . . . .
S12 S -0.19780(5) 0.32730(5) 0.31205(3) 0.0178 1.0000 Uani . . . . . .
O13 O -0.05519(13) 0.08482(13) 0.18017(8) 0.0157 1.0000 Uani . . . . . .
C14 C -0.0873(2) -0.06887(19) 0.23427(12) 0.0202 1.0000 Uani . . . . . .
C15 C -0.2228(2) -0.21282(19) 0.17489(12) 0.0202 1.0000 Uani . . . . . .
O16 O -0.33218(13) 0.18872(13) 0.10587(8) 0.0143 1.0000 Uani . . . . . .
C17 C -0.48913(19) 0.28153(19) 0.09581(12) 0.0166 1.0000 Uani . . . . . .
C18 C -0.65510(19) 0.1472(2) 0.08646(12) 0.0198 1.0000 Uani . . . . . .
C19 C 0.2296(2) 0.77170(19) 0.43268(11) 0.0155 1.0000 Uani . . . . . .
C20 C 0.2030(2) 0.9304(2) 0.47748(11) 0.0171 1.0000 Uani . . . . . .
H31 H 0.4391 1.1942 0.3607 0.0213 1.0000 Uiso R . . . . .
H41 H 0.4808 0.9326 0.2864 0.0214 1.0000 Uiso R . . . . .
H61 H 0.4138 0.5252 0.3656 0.0165 1.0000 Uiso R . . . . .
H62 H 0.4509 0.6091 0.2694 0.0161 1.0000 Uiso R . . . . .
H141 H -0.1202 -0.0340 0.2981 0.0251 1.0000 Uiso R . . . . .
H142 H 0.0236 -0.1123 0.2428 0.0256 1.0000 Uiso R . . . . .
H151 H -0.2319 -0.3109 0.2115 0.0303 1.0000 Uiso R . . . . .
H153 H -0.3385 -0.1737 0.1621 0.0320 1.0000 Uiso R . . . . .
H152 H -0.1830 -0.2459 0.1200 0.0342 1.0000 Uiso R . . . . .
H171 H -0.4794 0.3676 0.1486 0.0211 1.0000 Uiso R . . . . .
H172 H -0.4923 0.3470 0.0382 0.0235 1.0000 Uiso R . . . . .
H181 H -0.7590 0.2055 0.0760 0.0320 1.0000 Uiso R . . . . .
H182 H -0.6653 0.0888 0.1416 0.0338 1.0000 Uiso R . . . . .
H183 H -0.6568 0.0509 0.0414 0.0310 1.0000 Uiso R . . . . .
H191 H 0.1793 0.6646 0.4502 0.0178 1.0000 Uiso R . . . . .
H201 H 0.1308 0.9384 0.5271 0.0227 1.0000 Uiso R . . . . .
H101 H -0.0761 0.3988 0.0713 0.0155 1.0000 Uiso R . . . . .
H71 H 0.1303 0.4228 0.2936 0.0149 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'
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'
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'
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'
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
Cl1 . C2 . C3 . 119.53(11) yes
Cl1 . C2 . C20 . 118.98(12) yes
C3 . C2 . C20 . 121.48(13) yes
C2 . C3 . C4 . 118.78(13) yes
C2 . C3 . H31 . 120.1 no
C4 . C3 . H31 . 120.9 no
C3 . C4 . C5 . 121.07(14) yes
C3 . C4 . H41 . 117.0 no
C5 . C4 . H41 . 122.0 no
C4 . C5 . C6 . 120.86(13) yes
C4 . C5 . C19 . 118.81(13) yes
C6 . C5 . C19 . 120.32(12) yes
C5 . C6 . N7 . 112.67(11) yes
C5 . C6 . H61 . 107.8 no
N7 . C6 . H61 . 106.8 no
C5 . C6 . H62 . 112.5 no
N7 . C6 . H62 . 109.3 no
H61 . C6 . H62 . 107.5 no
C6 . N7 . C8 . 123.97(12) yes
C6 . N7 . H71 . 118.8 no
C8 . N7 . H71 . 116.3 no
N7 . C8 . S9 . 123.07(10) yes
N7 . C8 . N10 . 117.15(12) yes
S9 . C8 . N10 . 119.78(11) yes
C8 . N10 . P11 . 129.28(10) yes
C8 . N10 . H101 . 115.9 no
P11 . N10 . H101 . 114.5 no
N10 . P11 . S12 . 114.70(4) yes
N10 . P11 . O13 . 101.81(6) yes
S12 . P11 . O13 . 115.90(5) yes
N10 . P11 . O16 . 102.34(6) yes
S12 . P11 . O16 . 116.58(4) yes
O13 . P11 . O16 . 103.48(6) yes
P11 . O13 . C14 . 123.23(9) yes
O13 . C14 . C15 . 111.20(12) yes
O13 . C14 . H141 . 111.3 no
C15 . C14 . H141 . 112.8 no
O13 . C14 . H142 . 103.9 no
C15 . C14 . H142 . 106.3 no
H141 . C14 . H142 . 110.9 no
C14 . C15 . H151 . 107.5 no
C14 . C15 . H153 . 109.8 no
H151 . C15 . H153 . 108.9 no
C14 . C15 . H152 . 109.5 no
H151 . C15 . H152 . 108.2 no
H153 . C15 . H152 . 112.7 no
P11 . O16 . C17 . 123.71(9) yes
O16 . C17 . C18 . 108.43(11) yes
O16 . C17 . H171 . 111.0 no
C18 . C17 . H171 . 111.8 no
O16 . C17 . H172 . 109.1 no
C18 . C17 . H172 . 110.7 no
H171 . C17 . H172 . 105.8 no
C17 . C18 . H181 . 109.2 no
C17 . C18 . H182 . 114.6 no
H181 . C18 . H182 . 104.8 no
C17 . C18 . H183 . 112.7 no
H181 . C18 . H183 . 114.9 no
H182 . C18 . H183 . 100.3 no
C5 . C19 . C20 . 121.03(13) yes
C5 . C19 . H191 . 118.0 no
C20 . C19 . H191 . 121.0 no
C2 . C20 . C19 . 118.83(14) yes
C2 . C20 . H201 . 117.5 no
C19 . C20 . H201 . 123.6 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
Cl1 . C2 . 1.7495(14) yes
C2 . C3 . 1.382(2) yes
C2 . C20 . 1.388(2) yes
C3 . C4 . 1.391(2) yes
C3 . H31 . 0.920 no
C4 . C5 . 1.389(2) yes
C4 . H41 . 0.919 no
C5 . C6 . 1.5141(19) yes
C5 . C19 . 1.393(2) yes
C6 . N7 . 1.4650(17) yes
C6 . H61 . 0.994 no
C6 . H62 . 0.983 no
N7 . C8 . 1.3341(18) yes
N7 . H71 . 0.860 no
C8 . S9 . 1.6839(14) yes
C8 . N10 . 1.3772(18) yes
N10 . P11 . 1.6731(12) yes
N10 . H101 . 0.871 no
P11 . S12 . 1.9306(5) yes
P11 . O13 . 1.5676(10) yes
P11 . O16 . 1.5671(10) yes
O13 . C14 . 1.4647(17) yes
C14 . C15 . 1.499(2) yes
C14 . H141 . 1.002 no
C14 . H142 . 0.945 no
C15 . H151 . 0.944 no
C15 . H153 . 0.965 no
C15 . H152 . 0.908 no
O16 . C17 . 1.4686(16) yes
C17 . C18 . 1.498(2) yes
C17 . H171 . 0.944 no
C17 . H172 . 0.985 no
C18 . H181 . 0.959 no
C18 . H182 . 0.935 no
C18 . H183 . 0.936 no
C19 . C20 . 1.386(2) yes
C19 . H191 . 0.925 no
C20 . H201 . 0.963 no
loop_
_oxford_refln_omitted_index_h
_oxford_refln_omitted_index_k
_oxford_refln_omitted_index_l
_oxford_refln_omitted_flag
_oxford_refln_omitted_details
-1 2 16 x .
