#------------------------------------------------------------------------------
#$Date: 2023-05-06 13:49:30 +0300 (Sat, 06 May 2023) $
#$Revision: 283598 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/27/2022732.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_2022732
loop_
_publ_author_name
'Kaminsky, Werner'
'Kaganyuk, Max'
_publ_section_title
;
 Enanti-opure (S)-butan-2-yl
 N-(4-x-phen-yl)thio-carbamates, x = NO₂,
 OCH₃, F, and Cl.
;
_journal_issue                   'Pt 4'
_journal_name_full
'Acta crystallographica. Section E, Crystallographic communications'
_journal_page_first              386
_journal_page_last               391
_journal_paper_doi               10.1107/S2056989023002591
_journal_volume                  79
_journal_year                    2023
_chemical_absolute_configuration rmad
_chemical_formula_iupac          'C11 H14 Cl N O S'
_chemical_formula_moiety         'C11 H14 Cl N O S'
_chemical_formula_sum            'C11 H14 Cl N O S'
_chemical_formula_weight         243.74
_chemical_name_systematic
;
(S)-2-Butyl N-(4-chlorophenyl)thiocarbamate
;
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 105.592(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.4173(15)
_cell_length_b                   5.0170(5)
_cell_length_c                   16.2502(15)
_cell_measurement_reflns_used    9275
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      33.09
_cell_measurement_theta_min      2.6
_cell_volume                     1210.7(2)
_computing_cell_refinement
;
SAINT (Bruker, 2012)
;
_computing_data_collection
;
APEX2 (Bruker, 2012)
;
_computing_data_reduction
;
SORTAV (Blessing, 1995)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
WinGX publication routines (Farrugia, 2012)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'APEX-II CCD'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       'φ or ω oscillation scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            46534
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.298
_diffrn_reflns_theta_min         2.129
_diffrn_source                   'sealed x-ray tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.462
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.954
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prsm
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.221
_refine_ls_abs_structure_details
;
Flack x determined using 2891 quotients
[(I⁺)-(I⁻)]/[(I⁺)+(I⁻)]
(Parsons et al.,  2013).
;
_refine_ls_abs_structure_Flack   0.022(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     281
_refine_ls_number_reflns         9292
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0332
_refine_ls_R_factor_gt           0.0272
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0312P)²+0.1769P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0631
_refine_ls_wR_factor_ref         0.0663
_reflns_number_gt                8469
_reflns_number_total             9292
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            zl5044sup1.cif
_cod_data_source_block           IV
_cod_depositor_comments
'Adding full bibliography for 2022729--2022732.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2022732
_cod_database_fobs_code          2022732
_shelx_estimated_absorpt_t_min   0.769
_shelx_estimated_absorpt_t_max   0.951
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
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
C C1 0.35185(9) 0.0662(3) 0.14953(8) 0.0139(2) Uani d 1 . .
C C2 0.41945(10) 0.0839(4) 0.10745(9) 0.0190(3) Uani d 1 . .
H H2A 0.467553 0.206748 0.126558 0.023 Uiso calc 1 . .
C C3 0.41621(10) -0.0787(4) 0.03751(10) 0.0192(3) Uani d 1 . .
H H3 0.461955 -0.066932 0.008467 0.023 Uiso calc 1 . .
C C4 0.34615(10) -0.2577(3) 0.01033(9) 0.0166(3) Uani d 1 . .
C C5 0.27962(11) -0.2816(4) 0.05240(10) 0.0205(3) Uani d 1 . .
H H5 0.232416 -0.407588 0.033739 0.025 Uiso calc 1 . .
C C6 0.28265(10) -0.1197(3) 0.12206(10) 0.0187(3) Uani d 1 . .
H H6 0.23729 -0.135039 0.151438 0.022 Uiso calc 1 . .
C C7 0.40912(9) 0.3612(3) 0.27658(9) 0.0143(3) Uani d 1 . .
C C8 0.58731(11) 0.2067(4) 0.41659(10) 0.0234(3) Uani d 1 . .
H H8A 0.533102 0.191469 0.436836 0.035 Uiso calc 1 . .
H H8B 0.63713 0.274749 0.46281 0.035 Uiso calc 1 . .
H H8C 0.60323 0.030984 0.398713 0.035 Uiso calc 1 . .
C C9 0.56953(10) 0.3964(3) 0.34164(9) 0.0152(3) Uani d 1 . .
H H9 0.555206 0.577305 0.3603 0.018 Uiso calc 1 . .
C C10 0.64685(10) 0.4172(3) 0.30082(10) 0.0183(3) Uani d 1 . .
H H10A 0.658195 0.239034 0.279654 0.022 Uiso calc 1 . .
H H10B 0.701819 0.471755 0.344903 0.022 Uiso calc 1 . .
C C11 0.62976(12) 0.6144(4) 0.22712(11) 0.0246(3) Uani d 1 . .
H H11A 0.578675 0.553323 0.180904 0.037 Uiso calc 1 . .
H H11B 0.68351 0.627046 0.206055 0.037 Uiso calc 1 . .
H H11C 0.616089 0.790011 0.246922 0.037 Uiso calc 1 . .
C C12 0.15284(10) 0.8652(3) 0.36586(9) 0.0139(3) Uani d 1 . .
C C13 0.08213(10) 0.8722(3) 0.40427(9) 0.0177(3) Uani d 1 . .
H H13 0.03196 0.756607 0.384976 0.021 Uiso calc 1 . .
C C14 0.08536(10) 1.0489(4) 0.47084(9) 0.0188(3) Uani d 1 . .
H H14 0.037264 1.054228 0.497095 0.023 Uiso calc 1 . .
C C15 0.15837(10) 1.2168(3) 0.49896(9) 0.0156(3) Uani d 1 . .
C C16 0.22863(10) 1.2164(3) 0.46032(10) 0.0173(3) Uani d 1 . .
H H16 0.278113 1.334668 0.479234 0.021 Uiso calc 1 . .
C C17 0.22527(9) 1.0408(3) 0.39386(9) 0.0163(3) Uani d 1 . .
H H17 0.272809 1.03958 0.366869 0.02 Uiso calc 1 . .
C C18 0.09692(9) 0.5412(3) 0.24559(8) 0.0143(2) Uani d 1 . .
C C19 -0.11540(12) 0.3508(5) 0.25809(12) 0.0303(4) Uani d 1 . .
H H19A -0.07721 0.226643 0.298634 0.045 Uiso calc 1 . .
H H19B -0.170239 0.25891 0.226207 0.045 Uiso calc 1 . .
H H19C -0.131607 0.50161 0.289328 0.045 Uiso calc 1 . .
C C20 -0.06464(10) 0.4518(4) 0.19644(10) 0.0196(3) Uani d 1 . .
H H20 -0.043938 0.297952 0.16748 0.024 Uiso calc 1 . .
C C21 -0.11786(11) 0.6453(4) 0.13017(11) 0.0285(4) Uani d 1 . .
H H21A -0.133859 0.802766 0.159794 0.034 Uiso calc 1 . .
H H21B -0.174639 0.558583 0.098314 0.034 Uiso calc 1 . .
C C22 -0.06701(14) 0.7390(6) 0.06654(13) 0.0423(6) Uani d 1 . .
H H22A -0.011127 0.827881 0.097427 0.063 Uiso calc 1 . .
H H22B -0.104658 0.864221 0.02596 0.063 Uiso calc 1 . .
H H22C -0.052677 0.58506 0.035482 0.063 Uiso calc 1 . .
N N1 0.34513(8) 0.2393(3) 0.21636(8) 0.0161(2) Uani d 1 . .
H H1 0.2928(13) 0.275(5) 0.2178(12) 0.019 Uiso d 1 . .
N N2 0.15996(8) 0.6818(3) 0.30193(8) 0.0148(2) Uani d 1 . .
H H2 0.2126(13) 0.652(4) 0.3009(12) 0.018 Uiso d 1 . .
O O1 0.49217(6) 0.2959(2) 0.27480(6) 0.0150(2) Uani d 1 . .
O O2 0.01363(7) 0.5970(2) 0.24906(7) 0.0169(2) Uani d 1 . .
S S1 0.38309(2) 0.57287(9) 0.34614(2) 0.02056(8) Uani d 1 . .
S S2 0.12456(2) 0.32279(9) 0.17890(2) 0.01850(8) Uani d 1 . .
Cl Cl1 0.34068(3) -0.45232(9) -0.07979(2) 0.02263(8) Uani d 1 . .
Cl Cl2 0.16375(3) 1.43009(8) 0.58491(2) 0.02094(8) Uani 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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 -1 0.013
1 0 1 0.058
5 -1 2 0.153
-5 1 -2 0.328
1 0 -1 0.055
-1 0 1 0.045
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
C2 C1 C6 . . 119.55(14) ?
C2 C1 N1 . . 123.74(14) ?
C6 C1 N1 . . 116.58(12) ?
C3 C2 C1 . . 119.78(15) ?
C3 C2 H2A . . 120.1 ?
C1 C2 H2A . . 120.1 ?
C4 C3 C2 . . 119.74(14) ?
C4 C3 H3 . . 120.1 ?
C2 C3 H3 . . 120.1 ?
C5 C4 C3 . . 121.20(14) ?
C5 C4 Cl1 . . 119.48(12) ?
C3 C4 Cl1 . . 119.31(12) ?
C4 C5 C6 . . 119.16(15) ?
C4 C5 H5 . . 120.4 ?
C6 C5 H5 . . 120.4 ?
C5 C6 C1 . . 120.55(14) ?
C5 C6 H6 . . 119.7 ?
C1 C6 H6 . . 119.7 ?
O1 C7 N1 . . 113.38(13) ?
O1 C7 S1 . . 125.26(11) ?
N1 C7 S1 . . 121.35(11) ?
C9 C8 H8A . . 109.5 ?
C9 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C9 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
O1 C9 C8 . . 108.35(12) ?
O1 C9 C10 . . 106.11(11) ?
C8 C9 C10 . . 113.72(13) ?
O1 C9 H9 . . 109.5 ?
C8 C9 H9 . . 109.5 ?
C10 C9 H9 . . 109.5 ?
C9 C10 C11 . . 113.53(13) ?
C9 C10 H10A . . 108.9 ?
C11 C10 H10A . . 108.9 ?
C9 C10 H10B . . 108.9 ?
C11 C10 H10B . . 108.9 ?
H10A C10 H10B . . 107.7 ?
C10 C11 H11A . . 109.5 ?
C10 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C10 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
C13 C12 C17 . . 119.34(13) ?
C13 C12 N2 . . 124.73(14) ?
C17 C12 N2 . . 115.86(13) ?
C14 C13 C12 . . 119.74(14) ?
C14 C13 H13 . . 120.1 ?
C12 C13 H13 . . 120.1 ?
C15 C14 C13 . . 120.14(13) ?
C15 C14 H14 . . 119.9 ?
C13 C14 H14 . . 119.9 ?
C14 C15 C16 . . 120.93(14) ?
C14 C15 Cl2 . . 119.89(12) ?
C16 C15 Cl2 . . 119.18(12) ?
C17 C16 C15 . . 118.89(14) ?
C17 C16 H16 . . 120.6 ?
C15 C16 H16 . . 120.6 ?
C16 C17 C12 . . 120.93(13) ?
C16 C17 H17 . . 119.5 ?
C12 C17 H17 . . 119.5 ?
O2 C18 N2 . . 112.99(13) ?
O2 C18 S2 . . 125.57(11) ?
N2 C18 S2 . . 121.44(11) ?
C20 C19 H19A . . 109.5 ?
C20 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
C20 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
O2 C20 C19 . . 105.68(13) ?
O2 C20 C21 . . 107.36(14) ?
C19 C20 C21 . . 113.99(14) ?
O2 C20 H20 . . 109.9 ?
C19 C20 H20 . . 109.9 ?
C21 C20 H20 . . 109.9 ?
C20 C21 C22 . . 113.51(15) ?
C20 C21 H21A . . 108.9 ?
C22 C21 H21A . . 108.9 ?
C20 C21 H21B . . 108.9 ?
C22 C21 H21B . . 108.9 ?
H21A C21 H21B . . 107.7 ?
C21 C22 H22A . . 109.5 ?
C21 C22 H22B . . 109.5 ?
H22A C22 H22B . . 109.5 ?
C21 C22 H22C . . 109.5 ?
H22A C22 H22C . . 109.5 ?
H22B C22 H22C . . 109.5 ?
C7 N1 C1 . . 130.59(13) ?
C7 N1 H1 . . 114.2(15) ?
C1 N1 H1 . . 115.2(15) ?
C18 N2 C12 . . 131.16(13) ?
C18 N2 H2 . . 115.1(14) ?
C12 N2 H2 . . 113.7(14) ?
C7 O1 C9 . . 119.61(11) ?
C18 O2 C20 . . 121.44(12) ?
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
C1 C2 . 1.3945(19) ?
C1 C6 . 1.397(2) ?
C1 N1 . 1.4160(19) ?
C2 C3 . 1.389(2) ?
C2 H2A . 0.95 ?
C3 C4 . 1.383(2) ?
C3 H3 . 0.95 ?
C4 C5 . 1.382(2) ?
C4 Cl1 . 1.7432(16) ?
C5 C6 . 1.384(2) ?
C5 H5 . 0.95 ?
C6 H6 . 0.95 ?
C7 O1 . 1.3296(17) ?
C7 N1 . 1.3364(19) ?
C7 S1 . 1.6763(15) ?
C8 C9 . 1.512(2) ?
C8 H8A . 0.98 ?
C8 H8B . 0.98 ?
C8 H8C . 0.98 ?
C9 O1 . 1.4698(17) ?
C9 C10 . 1.516(2) ?
C9 H9 . 1 ?
C10 C11 . 1.521(2) ?
C10 H10A . 0.99 ?
C10 H10B . 0.99 ?
C11 H11A . 0.98 ?
C11 H11B . 0.98 ?
C11 H11C . 0.98 ?
C12 C13 . 1.395(2) ?
C12 C17 . 1.399(2) ?
C12 N2 . 1.4138(19) ?
C13 C14 . 1.389(2) ?
C13 H13 . 0.95 ?
C14 C15 . 1.382(2) ?
C14 H14 . 0.95 ?
C15 C16 . 1.390(2) ?
C15 Cl2 . 1.7436(16) ?
C16 C17 . 1.384(2) ?
C16 H16 . 0.95 ?
C17 H17 . 0.95 ?
C18 O2 . 1.3301(17) ?
C18 N2 . 1.3425(18) ?
C18 S2 . 1.6747(16) ?
C19 C20 . 1.515(2) ?
C19 H19A . 0.98 ?
C19 H19B . 0.98 ?
C19 H19C . 0.98 ?
C20 O2 . 1.4708(18) ?
C20 C21 . 1.517(3) ?
C20 H20 . 1 ?
C21 C22 . 1.530(3) ?
C21 H21A . 0.99 ?
C21 H21B . 0.99 ?
C22 H22A . 0.98 ?
C22 H22B . 0.98 ?
C22 H22C . 0.98 ?
N1 H1 . 0.83(2) ?
N2 H2 . 0.829(19) ?
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 H1 S2 . 0.83(2) 2.511(19) 3.3163(13) 163.0(18) yes
N2 H2 S1 . 0.829(19) 2.563(19) 3.3645(13) 162.8(17) yes
C6 H6 S2 . 0.95 2.99 3.5961(17) 123.3 yes
C17 H17 S1 . 0.95 2.97 3.6122(16) 126.5 yes
C2 H2A O1 . 0.95 2.38 2.8539(18) 110.6 yes
C13 H13 O2 . 0.95 2.29 2.8197(19) 114.2 yes
