#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/23/4502386.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_4502386
loop_
_publ_author_name
'Kobayashi, Yuka'
'Maeda, Jin'
'Ando, Tetsuo'
'Saigo, Kazuhiko'
_publ_section_title
;
 Halogen-Bonding Interaction Stabilizing Cluster-type Diastereomeric Salt
 Crystals
;
_journal_issue                   2
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              685
_journal_paper_doi               10.1021/cg9010967
_journal_volume                  10
_journal_year                    2010
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C16 H20 Cl F N O2 P S '
_chemical_formula_sum            'C16 H20 Cl F N O2 P S'
_chemical_formula_weight         375.82
_chemical_melting_point          438
_chemical_name_common
;
(R)-1-(p-fluorophenyl)ethylammonium_(Rp)-O-ethyl(p-chlorophenyl)phosphonothioate
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      5
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_cell_angle_alpha                90
_cell_angle_beta                 108.738(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   22.30(3)
_cell_length_b                   7.399(10)
_cell_length_c                   11.91(2)
_cell_measurement_reflns_used    2096
_cell_measurement_temperature    103.1
_cell_measurement_theta_max      31.5
_cell_measurement_theta_min      1.8
_cell_volume                     1861(5)
_computing_cell_refinement       CrystalClear
_computing_data_collection       CrystalClear
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.6.0'
_computing_structure_refinement  CRYSTALS
_computing_structure_solution    SIR92
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.5700
_diffrn_measured_fraction_theta_max 0.5700
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.082
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4788
_diffrn_reflns_theta_full        31.30
_diffrn_reflns_theta_max         31.30
_exptl_absorpt_coefficient_mu    0.420
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             784.00
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.15
_refine_diff_density_max         1.03
_refine_diff_density_min         -0.96
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.309
_refine_ls_hydrogen_treatment    noref
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3599
_refine_ls_R_factor_gt           0.0650
_refine_ls_shift/su_max          0.0030
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
'w = 1/[0.0010Fo² + 3.0000σ(Fo²) + 0.5000]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0800
_reflns_number_gt                3599
_reflns_number_total             4788
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            cg9010967_si_001.cif
_cod_data_source_block           '__(Rp)-1_(R)-2a'
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '438 K' was changed to '438' - the
value should be numeric and without a unit designator.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1860.1(44)
_cod_original_formula_sum        'C16 H20 Cl F N O2 P S '
_cod_database_code               4502386
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,+Y,-Z
3 1/2+X,1/2+Y,+Z
4 1/2-X,1/2+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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Cl(2) Cl 0.06294(11) 0.1446(4) -0.1670(2) 0.0613(8) Uani 1.00 1 d .
S(1) S 0.16941(10) -0.5573(3) 0.2789(2) 0.0350(6) Uani 1.00 1 d .
P(1) P 0.13976(10) -0.3151(3) 0.3048(2) 0.0292(6) Uani 1.00 1 d .
F(1) F 0.2695(3) 0.2531(7) 0.1279(6) 0.092(2) Uani 1.00 1 d .
O(1) O 0.0752(2) -0.3221(6) 0.3369(4) 0.0279(13) Uani 1.00 1 d .
O(2) O 0.1832(2) -0.2047(6) 0.4041(4) 0.030(2) Uani 1.00 1 d .
N(1) N 0.3020(3) -0.3573(7) 0.5051(5) 0.030(2) Uani 1.00 1 d .
C(8) C 0.0999(4) -0.0072(9) 0.1692(6) 0.030(3) Uani 1.00 1 d .
C(9) C 0.3188(4) -0.1919(10) 0.3381(7) 0.032(3) Uani 1.00 1 d .
C(10) C 0.1222(4) -0.2608(10) 0.0655(7) 0.037(3) Uani 1.00 1 d .
C(11) C 0.3370(4) -0.3601(9) 0.4140(7) 0.038(3) Uani 1.00 1 d .
C(12) C 0.1198(4) -0.1845(9) 0.1678(6) 0.029(2) Uani 1.00 1 d .
C(13) C 0.2933(4) -0.2090(11) 0.2171(9) 0.049(3) Uani 1.00 1 d .
C(14) C 0.3272(4) -0.0251(9) 0.3884(7) 0.043(3) Uani 1.00 1 d .
C(15) C -0.0303(4) -0.4238(10) 0.3169(7) 0.045(3) Uani 1.00 1 d .
C(16) C 0.0837(4) 0.0948(10) 0.0665(7) 0.038(3) Uani 1.00 1 d .
C(17) C 0.0868(4) 0.0202(10) -0.0352(7) 0.035(3) Uani 1.00 1 d .
C(18) C 0.0204(4) -0.4207(10) 0.2610(7) 0.045(3) Uani 1.00 1 d .
C(19) C 0.1060(4) -0.1557(12) -0.0390(8) 0.051(3) Uani 1.00 1 d .
C(20) C 0.4060(4) -0.3844(12) 0.4808(7) 0.057(3) Uani 1.00 1 d .
C(21) C 0.2777(4) -0.058(1) 0.1437(8) 0.059(3) Uani 1.00 1 d .
C(22) C 0.2860(4) 0.1092(12) 0.1973(10) 0.053(4) Uani 1.00 1 d .
C(23) C 0.3086(5) 0.1243(11) 0.3151(10) 0.060(4) Uani 1.00 1 d .
H(1) H 0.3276 -0.2974 0.5745 0.035 Uiso 1.00 1 c R
H(2) H 0.2937 -0.4772 0.5245 0.035 Uiso 1.00 1 c R
H(3) H 0.2631 -0.2940 0.4732 0.035 Uiso 1.00 1 c R
H(4) H 0.0993 0.0437 0.2421 0.035 Uiso 1.00 1 c R
H(5) H 0.1349 -0.3831 0.0639 0.044 Uiso 1.00 1 c R
H(6) H 0.3232 -0.4633 0.3650 0.050 Uiso 1.00 1 c R
H(7) H 0.2854 -0.3267 0.1837 0.058 Uiso 1.00 1 c R
H(8) H 0.3445 -0.0143 0.4722 0.055 Uiso 1.00 1 c R
H(9) H -0.0254 -0.5281 0.3655 0.059 Uiso 1.00 1 c R
H(10) H -0.0709 -0.4254 0.2582 0.059 Uiso 1.00 1 c R
H(11) H -0.0263 -0.3184 0.3644 0.059 Uiso 1.00 1 c R
H(12) H 0.0703 0.2170 0.0642 0.043 Uiso 1.00 1 c R
H(13) H 0.0052 -0.3608 0.1867 0.052 Uiso 1.00 1 c R
H(14) H 0.0320 -0.5411 0.2493 0.052 Uiso 1.00 1 c R
H(15) H 0.1085 -0.2042 -0.1112 0.059 Uiso 1.00 1 c R
H(16) H 0.4248 -0.2683 0.4993 0.069 Uiso 1.00 1 c R
H(17) H 0.4260 -0.4486 0.4335 0.069 Uiso 1.00 1 c R
H(18) H 0.4110 -0.4494 0.5521 0.069 Uiso 1.00 1 c R
H(19) H 0.2613 -0.0691 0.0599 0.073 Uiso 1.00 1 c R
H(20) H 0.3137 0.2425 0.3481 0.083 Uiso 1.00 1 c R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.000 0.000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
Cl Cl 0.148 0.159
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
F F 0.017 0.010
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.006 0.003
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.011 0.006
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
P P 0.102 0.094
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.125 0.123
;
International Tables for Crystallography
(1992, 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
Cl(2) C(17) C(16) 120.0(6)
Cl(2) C(17) C(19) 118.5(7)
S(1) P(1) O(1) 112.4(2)
S(1) P(1) O(2) 117.0(2)
S(1) P(1) C(12) 109.8(3)
O(2) P(1) O(1) 103.3(3)
C(12) P(1) O(1) 104.5(3)
P(1) O(1) C(18) 120.4(5)
C(12) P(1) O(2) 109.0(3)
P(1) C(12) C(10) 120.9(5)
P(1) C(12) C(8) 118.5(6)
F(1) C(22) C(21) 117.6(9)
F(1) C(22) C(23) 121.6(8)
O(1) C(18) C(15) 109.7(6)
N(1) C(11) C(9) 108.2(6)
N(1) C(11) C(20) 107.3(6)
C(16) C(8) C(12) 120.0(7)
C(8) C(12) C(10) 120.6(7)
C(8) C(16) C(17) 119.7(7)
C(13) C(9) C(11) 119.4(7)
C(14) C(9) C(11) 120.8(7)
C(9) C(11) C(20) 116.6(7)
C(14) C(9) C(13) 119.8(7)
C(9) C(13) C(21) 121.3(8)
C(9) C(14) C(23) 118.4(8)
C(19) C(10) C(12) 119.2(7)
C(10) C(19) C(17) 119.1(8)
C(13) C(21) C(22) 117.5(9)
C(14) C(23) C(22) 122.0(8)
C(16) C(17) C(19) 121.4(7)
C(21) C(22) C(23) 120.8(9)
O(1) C(18) H(14) 110.2580
O(1) C(18) H(13) 108.7208
H(2) N(1) C(11) 110.1650
H(3) N(1) C(11) 109.4000
N(1) C(11) H(6) 107.9746
H(1) N(1) C(11) 108.8379
H(2) N(1) H(1) 109.4742
H(3) N(1) H(1) 109.4721
H(3) N(1) H(2) 109.4753
H(4) C(8) C(12) 118.9540
C(8) C(16) H(12) 122.3734
H(4) C(8) C(16) 121.0299
C(9) C(11) H(6) 108.8037
C(9) C(13) H(7) 118.7965
C(9) C(14) H(8) 119.4524
H(5) C(10) C(12) 120.7736
C(10) C(19) H(15) 121.0460
H(5) C(10) C(19) 120.0206
H(6) C(11) C(20) 107.7356
C(11) C(20) H(16) 108.3794
C(11) C(20) H(17) 110.0789
C(11) C(20) H(18) 109.9484
H(7) C(13) C(21) 119.8872
C(13) C(21) H(19) 121.4188
C(14) C(23) H(20) 120.0944
H(8) C(14) C(23) 122.1009
C(15) C(18) H(14) 109.4751
C(15) C(18) H(13) 109.2164
H(9) C(15) C(18) 109.3139
H(10) C(15) C(18) 110.7262
H(11) C(15) C(18) 108.3595
H(10) C(15) H(9) 109.4750
H(11) C(15) H(9) 109.4732
H(11) C(15) H(10) 109.4707
H(12) C(16) C(17) 117.9310
C(17) C(19) H(15) 119.8168
H(14) C(18) H(13) 109.4573
H(17) C(20) H(16) 109.4653
H(18) C(20) H(16) 109.4761
H(18) C(20) H(17) 109.4735
H(19) C(21) C(22) 121.1091
C(22) C(23) H(20) 117.7927
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl(2) C(17) 1.747(8)
S(1) P(1) 1.968(3)
P(1) O(1) 1.604(5)
P(1) O(2) 1.506(5)
P(1) C(12) 1.824(7)
F(1) C(22) 1.32(1)
O(1) C(18) 1.460(8)
N(1) C(11) 1.53(1)
C(8) C(12) 1.39(1)
C(8) C(16) 1.38(1)
C(9) C(11) 1.51(1)
C(9) C(13) 1.37(1)
C(9) C(14) 1.36(1)
C(10) C(12) 1.36(1)
C(10) C(19) 1.41(1)
C(11) C(20) 1.50(1)
C(13) C(21) 1.39(1)
C(14) C(23) 1.39(1)
C(15) C(18) 1.48(1)
C(16) C(17) 1.35(1)
C(17) C(19) 1.37(1)
C(21) C(22) 1.37(1)
C(22) C(23) 1.33(2)
C(23) C(14) 1.39(1)
C(23) C(22) 1.33(2)
N(1) H(1) 0.9500
N(1) H(2) 0.9500
N(1) H(3) 0.9500
C(8) H(4) 0.9499
C(10) H(5) 0.9500
C(11) H(6) 0.9500
C(13) H(7) 0.9500
C(14) H(8) 0.9500
C(15) H(9) 0.9500
C(15) H(10) 0.9500
C(15) H(11) 0.9500
C(16) H(12) 0.9500
C(18) H(13) 0.9500
C(18) H(14) 0.9500
C(19) H(15) 0.9499
C(20) H(16) 0.9500
C(20) H(17) 0.9499
C(20) H(18) 0.9501
C(21) H(19) 0.9500
C(23) H(20) 0.9500
H(14) C(18) 0.9500
H(20) C(23) 0.9500
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
S(1) P(1) O(1) C(18) -52.3(5)
O(2) P(1) O(1) C(18) -179.3(4)
C(12) P(1) O(1) C(18) 66.7(5)
S(1) P(1) C(12) C(8) -177.9(5)
S(1) P(1) C(12) C(10) 4.5(7)
O(1) P(1) C(12) C(8) 61.4(6)
O(1) P(1) C(12) C(10) -116.3(7)
O(2) P(1) C(12) C(8) -48.5(7)
O(2) P(1) C(12) C(10) 133.8(6)
P(1) O(1) C(18) C(15) 173.7(5)
C(16) C(8) C(12) P(1) -179.2(6)
C(16) C(8) C(12) C(10) -1(1)
C(12) C(8) C(16) C(17) 0(1)
C(13) C(9) C(11) N(1) -123.7(8)
C(13) C(9) C(11) C(20) 115.4(9)
C(14) C(9) C(11) N(1) 56(1)
C(14) C(9) C(11) C(20) -64(1)
C(11) C(9) C(13) C(21) -177.9(9)
C(14) C(9) C(13) C(21) 2(1)
C(11) C(9) C(14) C(23) -178.8(9)
C(13) C(9) C(14) C(23) 1(1)
C(19) C(10) C(12) P(1) 179.5(6)
C(19) C(10) C(12) C(8) 1(1)
C(12) C(10) C(19) C(17) -1(1)
C(9) C(13) C(21) C(22) -3(1)
C(9) C(14) C(23) C(22) -3(1)
C(8) C(16) C(17) Cl(2) 177.1(7)
C(8) C(16) C(17) C(19) 0(1)
Cl(2) C(17) C(19) C(10) -176.8(7)
C(16) C(17) C(19) C(10) 0(1)
C(13) C(21) C(22) F(1) -178.1(9)
C(13) C(21) C(22) C(23) 0(1)
F(1) C(22) C(23) C(14) -178(1)
C(21) C(22) C(23) C(14) 2(1)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139144934
