##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method     'WinGX routine CIF_UPDATE'
_audit_conform_dict_name     cif_core.dic
_audit_conform_dict_version     2.4.5
_chemical_name_systematic
;
(S)-2-Butyl N-(4-nitrophenyl)thiocarbamate
;
_chemical_formula_moiety     'C11 H14 N2 O3 S'
_chemical_formula_sum     'C11 H14 N2 O3 S'
_chemical_formula_iupac     'C11 H14 N2 O3 S'
_chemical_formula_weight     254.3
_chemical_absolute_configuration     rmad
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21'
_symmetry_space_group_name_Hall     'P 2yb'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z'
_cell_length_a     16.052(2)
_cell_length_b     4.7635(6)
_cell_length_c     16.853(2)
_cell_angle_alpha     90
_cell_angle_beta     101.702(8)
_cell_angle_gamma     90
_cell_volume     1261.9(3)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     8016
_cell_measurement_theta_min     2.47
_cell_measurement_theta_max     32.26
_cell_measurement_temperature     100(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.6
_exptl_crystal_size_mid     0.122
_exptl_crystal_size_min     0.06
_exptl_crystal_density_diffrn     1.339
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     536
loop_
    _exptl_crystal_face_index_h
    _exptl_crystal_face_index_k
    _exptl_crystal_face_index_l
    _exptl_crystal_face_perp_dist
    -1 0 -1 0.012
    1 0 1 0.03
    -1 0 1 0.025
    1 0 -1 0.06
    -2 -1 -2 0.244
    2 1 2 0.519
_exptl_absorpt_coefficient_mu     0.255
_exptl_absorpt_correction_type     numerical
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_absorpt_correction_T_min     0.959
_exptl_absorpt_correction_T_max     1
_exptl_special_details
;
Crystals were mounted on a CryoloopTM (0.2--0.3mm, Hampton Research) with
Paratone (R) oil. Between 7 to 12 data sets were collected to cover full Ewald
spheres to a resolution of better than 0.75 Å. Crystals were held at 100 K
with a Cryostream cooler, mounted to a Bruker APEXII single crystal X-ray
diffractometer, Mo radiation (Bruker 2012), equipped with a fine-focus X-ray
tube, Miracol X-ray optical collimator, and CCD detector. Crystal-to-detector
distance was 40 mm and the exposure times were between 20 to 120 seconds per
frame for all sets, pending on sample size. The scan widths were 0.5°.
Crystal data, data collection, and structure refinement details are summarized
in Table 5. The data were integrated and scaled using SAINT,
SADABS within the APEX2 software package by Bruker (2012). Data work-up
was done with SAINT (Bruker, 2012). Structures were solved with SHELXS
 (Sheldrick, 2008), and refined with SHELXL (Sheldrick 2015).
;
_diffrn_ambient_temperature     100(2)
_diffrn_source     'sealed x-ray tube'
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker APEXII'
_diffrn_measurement_device     'κ-geometry diffractometer'
_diffrn_measurement_method     'φ or ω oscillation scans'
_diffrn_detector     'APEX-II CCD'
_diffrn_reflns_number     37641
_diffrn_reflns_av_R_equivalents     0.0467
_diffrn_reflns_av_unetI/netI     0.0516
_diffrn_reflns_theta_min     1.598
_diffrn_reflns_theta_max     33.274
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.993
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -24
_diffrn_reflns_limit_h_max     24
_diffrn_reflns_limit_k_min     -7
_diffrn_reflns_limit_k_max     7
_diffrn_reflns_limit_l_min     -25
_diffrn_reflns_limit_l_max     25
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     ?
_diffrn_radiation_probe     x-ray
_reflns_number_total     9553
_reflns_number_gt     7648
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0586
_refine_ls_R_factor_gt     0.0387
_refine_ls_wR_factor_gt     0.0761
_refine_ls_wR_factor_ref     0.0844
_refine_ls_goodness_of_fit_ref     1.01
_refine_ls_restrained_S_all     1.01
_refine_ls_number_reflns     9553
_refine_ls_number_parameters     317
_refine_ls_number_restraints     1
_refine_ls_number_constraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0311P)²+0.2393P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0
_refine_ls_shift/su_mean     0
_refine_diff_density_max     0.306
_refine_diff_density_min     -0.283
_refine_ls_extinction_method     none
_refine_ls_abs_structure_details
;
Flack x determined using 2891 quotients
[(I⁺)-(I⁻)]/[(I⁺)+(I⁻)]
(Parsons et al.,  2013).
;
_refine_ls_abs_structure_Flack     -0.02(3)
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'
_computing_data_collection
;
APEX2 (Bruker, 2012)
;
_computing_cell_refinement
;
SAINT (Bruker, 2012)
;
_computing_data_reduction
;
SORTAV (Blessing, 1995)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
WinGX publication routines (Farrugia, 2012)
;
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 0.15331(12) -0.1677(4) 0.84542(12) 0.0152(4) Uani d 1 . .
    C C2 0.12449(12) -0.0015(4) 0.77677(12) 0.0174(4) Uani d 1 . .
    H H2 0.151144 -0.016729 0.731506 0.021 Uiso calc 1 . .
    C C3 0.05799(13) 0.1841(4) 0.77393(13) 0.0180(4) Uani d 1 . .
    H H3 0.038254 0.295554 0.727155 0.022 Uiso calc 1 . .
    C C4 0.02066(13) 0.2038(4) 0.84101(13) 0.0177(4) Uani d 1 . .
    C C5 0.04839(13) 0.0434(5) 0.90953(12) 0.0201(4) Uani d 1 . .
    H H5 0.021711 0.061094 0.954713 0.024 Uiso calc 1 . .
    C C6 0.11491(13) -0.1429(4) 0.91239(13) 0.0198(4) Uani d 1 . .
    H H6 0.134354 -0.253052 0.959486 0.024 Uiso calc 1 . .
    C C7 0.27251(12) -0.5046(4) 0.89663(12) 0.0160(4) Uani d 1 . .
    C C8 0.39282(13) -0.4736(6) 1.07282(13) 0.0257(4) Uani d 1 . .
    H H8A 0.423896 -0.579353 1.119423 0.031 Uiso calc 1 . .
    H H8B 0.382833 -0.281755 1.089701 0.031 Uiso calc 1 . .
    H H8C 0.426392 -0.468052 1.030338 0.031 Uiso calc 1 . .
    C C9 0.30844(13) -0.6152(5) 1.04042(12) 0.0194(4) Uani d 1 . .
    H H9 0.318562 -0.810097 1.022493 0.023 Uiso calc 1 . .
    C C10 0.24760(13) -0.6239(5) 1.09819(13) 0.0223(4) Uani d 1 . .
    H H10A 0.192737 -0.703946 1.069676 0.027 Uiso calc 1 . .
    H H10B 0.236767 -0.429797 1.114471 0.027 Uiso calc 1 . .
    C C11 0.28090(15) -0.7970(5) 1.17392(13) 0.0251(5) Uani d 1 . .
    H H11A 0.235765 -0.819771 1.204789 0.03 Uiso calc 1 . .
    H H11B 0.32951 -0.700617 1.207476 0.03 Uiso calc 1 . .
    H H11C 0.298872 -0.981959 1.158234 0.03 Uiso calc 1 . .
    C C12 0.37889(12) -1.0550(4) 0.66160(12) 0.0145(4) Uani d 1 . .
    C C13 0.41365(12) -1.2037(4) 0.73232(12) 0.0162(4) Uani d 1 . .
    H H13 0.393993 -1.167115 0.780817 0.019 Uiso calc 1 . .
    C C14 0.47613(12) -1.4027(4) 0.73227(12) 0.0161(4) Uani d 1 . .
    H H14 0.499536 -1.504145 0.780133 0.019 Uiso calc 1 . .
    C C15 0.50388(11) -1.4511(4) 0.66101(12) 0.0143(3) Uani d 1 . .
    C C16 0.47042(12) -1.3078(4) 0.59063(12) 0.0171(4) Uani d 1 . .
    H H16 0.490499 -1.345659 0.542426 0.021 Uiso calc 1 . .
    C C17 0.40740(12) -1.1085(4) 0.59036(12) 0.0168(4) Uani d 1 . .
    H H17 0.383929 -1.009483 0.542073 0.02 Uiso calc 1 . .
    C C18 0.25910(11) -0.7200(4) 0.61245(11) 0.0144(3) Uani d 1 . .
    C C19 0.23833(14) -0.7059(6) 0.39684(13) 0.0263(4) Uani d 1 . .
    H H19A 0.199951 -0.630163 0.348897 0.032 Uiso calc 1 . .
    H H19B 0.250212 -0.903695 0.387626 0.032 Uiso calc 1 . .
    H H19C 0.291683 -0.599465 0.406889 0.032 Uiso calc 1 . .
    C C20 0.19702(12) -0.6818(4) 0.46925(11) 0.0164(4) Uani d 1 . .
    H H20 0.186765 -0.479585 0.480041 0.02 Uiso calc 1 . .
    C C21 0.11459(13) -0.8446(5) 0.46106(14) 0.0230(4) Uani d 1 . .
    H H21A 0.101425 -0.87198 0.515435 0.028 Uiso calc 1 . .
    H H21B 0.12168 -1.032074 0.437977 0.028 Uiso calc 1 . .
    C C22 0.04055(13) -0.6930(6) 0.40690(14) 0.0283(5) Uani d 1 . .
    H H22A -0.012029 -0.799175 0.405447 0.034 Uiso calc 1 . .
    H H22B 0.051502 -0.677764 0.351929 0.034 Uiso calc 1 . .
    H H22C 0.034616 -0.504726 0.428525 0.034 Uiso calc 1 . .
    N N1 0.21907(11) -0.3574(4) 0.83957(11) 0.0166(3) Uani d 1 . .
    H H1N 0.2270(15) -0.384(5) 0.7950(15) 0.02 Uiso d 1 . .
    N N2 -0.04965(11) 0.3997(4) 0.83882(11) 0.0228(4) Uani d 1 . .
    N N3 0.31755(10) -0.8517(4) 0.66917(10) 0.0151(3) Uani d 1 . .
    H H3N 0.3146(15) -0.810(5) 0.7178(15) 0.018 Uiso d 1 . .
    N N4 0.56963(10) -1.6622(3) 0.66027(10) 0.0173(3) Uani d 1 . .
    O O1 -0.07477(11) 0.5356(4) 0.77657(10) 0.0371(4) Uani d 1 . .
    O O2 -0.08002(10) 0.4226(4) 0.89972(10) 0.0296(4) Uani d 1 . .
    O O3 0.26222(9) -0.4523(3) 0.97083(8) 0.0185(3) Uani d 1 . .
    O O4 0.59552(10) -1.7972(3) 0.72206(9) 0.0257(4) Uani d 1 . .
    O O5 0.59525(9) -1.6972(4) 0.59691(9) 0.0246(3) Uani d 1 . .
    O O6 0.25984(9) -0.8002(3) 0.53765(8) 0.0168(3) Uani d 1 . .
    S S1 0.34368(3) -0.72622(11) 0.87190(3) 0.01983(11) Uani d 1 . .
    S S2 0.19349(3) -0.48150(11) 0.63883(3) 0.01827(10) Uani d 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C6 . 1.396(3) ?
    C1 C2 . 1.401(3) ?
    C1 N1 . 1.408(2) ?
    C2 C3 . 1.379(3) ?
    C2 H2 . 0.95 ?
    C3 C4 . 1.386(3) ?
    C3 H3 . 0.95 ?
    C4 C5 . 1.381(3) ?
    C4 N2 . 1.459(3) ?
    C5 C6 . 1.382(3) ?
    C5 H5 . 0.95 ?
    C6 H6 . 0.95 ?
    C7 O3 . 1.318(2) ?
    C7 N1 . 1.348(2) ?
    C7 S1 . 1.669(2) ?
    C8 C9 . 1.512(3) ?
    C8 H8A . 0.98 ?
    C8 H8B . 0.98 ?
    C8 H8C . 0.98 ?
    C9 O3 . 1.475(2) ?
    C9 C10 . 1.513(3) ?
    C9 H9 . 1 ?
    C10 C11 . 1.522(3) ?
    C10 H10A . 0.99 ?
    C10 H10B . 0.99 ?
    C11 H11A . 0.98 ?
    C11 H11B . 0.98 ?
    C11 H11C . 0.98 ?
    C12 C17 . 1.392(3) ?
    C12 C13 . 1.401(3) ?
    C12 N3 . 1.405(2) ?
    C13 C14 . 1.380(3) ?
    C13 H13 . 0.95 ?
    C14 C15 . 1.382(3) ?
    C14 H14 . 0.95 ?
    C15 C16 . 1.379(3) ?
    C15 N4 . 1.460(2) ?
    C16 C17 . 1.387(3) ?
    C16 H16 . 0.95 ?
    C17 H17 . 0.95 ?
    C18 O6 . 1.320(2) ?
    C18 N3 . 1.350(2) ?
    C18 S2 . 1.669(2) ?
    C19 C20 . 1.507(3) ?
    C19 H19A . 0.98 ?
    C19 H19B . 0.98 ?
    C19 H19C . 0.98 ?
    C20 O6 . 1.481(2) ?
    C20 C21 . 1.516(3) ?
    C20 H20 . 1 ?
    C21 C22 . 1.525(3) ?
    C21 H21A . 0.99 ?
    C21 H21B . 0.99 ?
    C22 H22A . 0.98 ?
    C22 H22B . 0.98 ?
    C22 H22C . 0.98 ?
    N1 H1N . 0.80(2) ?
    N2 O2 . 1.227(2) ?
    N2 O1 . 1.229(2) ?
    N3 H3N . 0.85(2) ?
    N4 O4 . 1.223(2) ?
    N4 O5 . 1.231(2) ?
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
    C6 C1 C2 . . 119.58(18) ?
    C6 C1 N1 . . 124.81(18) ?
    C2 C1 N1 . . 115.58(17) ?
    C3 C2 C1 . . 120.96(19) ?
    C3 C2 H2 . . 119.5 ?
    C1 C2 H2 . . 119.5 ?
    C2 C3 C4 . . 118.36(19) ?
    C2 C3 H3 . . 120.8 ?
    C4 C3 H3 . . 120.8 ?
    C5 C4 C3 . . 121.68(18) ?
    C5 C4 N2 . . 119.43(18) ?
    C3 C4 N2 . . 118.89(18) ?
    C4 C5 C6 . . 120.01(19) ?
    C4 C5 H5 . . 120 ?
    C6 C5 H5 . . 120 ?
    C5 C6 C1 . . 119.41(19) ?
    C5 C6 H6 . . 120.3 ?
    C1 C6 H6 . . 120.3 ?
    O3 C7 N1 . . 113.22(17) ?
    O3 C7 S1 . . 125.47(15) ?
    N1 C7 S1 . . 121.30(15) ?
    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 ?
    O3 C9 C8 . . 108.78(18) ?
    O3 C9 C10 . . 103.89(16) ?
    C8 C9 C10 . . 115.33(17) ?
    O3 C9 H9 . . 109.5 ?
    C8 C9 H9 . . 109.5 ?
    C10 C9 H9 . . 109.5 ?
    C9 C10 C11 . . 113.06(18) ?
    C9 C10 H10A . . 109 ?
    C11 C10 H10A . . 109 ?
    C9 C10 H10B . . 109 ?
    C11 C10 H10B . . 109 ?
    H10A C10 H10B . . 107.8 ?
    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 ?
    C17 C12 C13 . . 119.81(17) ?
    C17 C12 N3 . . 124.28(18) ?
    C13 C12 N3 . . 115.89(17) ?
    C14 C13 C12 . . 120.70(18) ?
    C14 C13 H13 . . 119.6 ?
    C12 C13 H13 . . 119.6 ?
    C13 C14 C15 . . 118.51(18) ?
    C13 C14 H14 . . 120.7 ?
    C15 C14 H14 . . 120.7 ?
    C16 C15 C14 . . 121.78(18) ?
    C16 C15 N4 . . 119.32(17) ?
    C14 C15 N4 . . 118.90(17) ?
    C15 C16 C17 . . 119.87(19) ?
    C15 C16 H16 . . 120.1 ?
    C17 C16 H16 . . 120.1 ?
    C16 C17 C12 . . 119.32(18) ?
    C16 C17 H17 . . 120.3 ?
    C12 C17 H17 . . 120.3 ?
    O6 C18 N3 . . 113.71(17) ?
    O6 C18 S2 . . 125.43(14) ?
    N3 C18 S2 . . 120.85(15) ?
    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 ?
    O6 C20 C19 . . 105.04(15) ?
    O6 C20 C21 . . 108.67(15) ?
    C19 C20 C21 . . 114.00(18) ?
    O6 C20 H20 . . 109.7 ?
    C19 C20 H20 . . 109.7 ?
    C21 C20 H20 . . 109.7 ?
    C20 C21 C22 . . 111.86(18) ?
    C20 C21 H21A . . 109.2 ?
    C22 C21 H21A . . 109.2 ?
    C20 C21 H21B . . 109.2 ?
    C22 C21 H21B . . 109.2 ?
    H21A C21 H21B . . 107.9 ?
    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 . . 131.41(18) ?
    C7 N1 H1N . . 112.9(18) ?
    C1 N1 H1N . . 115.7(18) ?
    O2 N2 O1 . . 123.36(19) ?
    O2 N2 C4 . . 118.18(18) ?
    O1 N2 C4 . . 118.46(18) ?
    C18 N3 C12 . . 130.92(18) ?
    C18 N3 H3N . . 114.0(16) ?
    C12 N3 H3N . . 115.0(16) ?
    O4 N4 O5 . . 123.50(17) ?
    O4 N4 C15 . . 118.46(17) ?
    O5 N4 C15 . . 118.04(16) ?
    C7 O3 C9 . . 121.03(16) ?
    C18 O6 C20 . . 119.80(15) ?
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 H1N S2 . 0.80(2) 2.62(2) 3.3762(19) 159(2) yes
    N3 H3N S1 . 0.85(2) 2.57(2) 3.4095(18) 166(2) yes
    C2 H2 S2 . 0.95 2.87 3.592(2) 133.7 yes
    C13 H13 S1 . 0.95 2.81 3.611(2) 142.0 yes
    C5 H5 O2 2_547 0.95 2.53 3.203(3) 128.0 yes
_shelx_estimated_absorpt_T_min     0.862
_shelx_estimated_absorpt_T_max     0.985
data_II
_audit_creation_method     'WinGX routine CIF_UPDATE'
_audit_conform_dict_name     cif_core.dic
_audit_conform_dict_version     2.4.5
_chemical_name_systematic
;
(S)-2-Butyl N-(4-methoxyphenyl)thiocarbamate
;
_chemical_formula_moiety     'C12 H17 N O2 S'
_chemical_formula_sum     'C12 H17 N O2 S'
_chemical_formula_iupac     'C12 H17 N O2 S'
_chemical_formula_weight     239.32
_chemical_absolute_configuration     rmad
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21'
_symmetry_space_group_name_Hall     'P 2yb'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z'
_cell_length_a     6.6973(5)
_cell_length_b     21.2076(17)
_cell_length_c     9.1899(7)
_cell_angle_alpha     90
_cell_angle_beta     102.868(5)
_cell_angle_gamma     90
_cell_volume     1272.49(17)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     21109
_cell_measurement_theta_min     1.92
_cell_measurement_theta_max     30.78
_cell_measurement_temperature     100(2)
_exptl_crystal_description     needle
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.6
_exptl_crystal_size_mid     0.48
_exptl_crystal_size_min     0.2
_exptl_crystal_density_diffrn     1.249
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     512
loop_
    _exptl_crystal_face_index_h
    _exptl_crystal_face_index_k
    _exptl_crystal_face_index_l
    _exptl_crystal_face_perp_dist
    0 1 0 0.1250
    0 -1 0 0.0500
    1 0 0 0.3410
    -1 0 0 0.3360
    0 2 1 0.1420
    0 -1 -2 0.0880
    0 1 -1 0.1160
    0 -1 1 0.0610
    2 -1 -2 0.3360
    -2 1 2 0.3600
_exptl_absorpt_coefficient_mu     0.241
_exptl_absorpt_correction_type     numerical
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_absorpt_correction_T_min     0.657
_exptl_absorpt_correction_T_max     0.745
_exptl_special_details
;
Crystals were mounted on a CryoloopTM (0.2--0.3mm, Hampton Research) with
Paratone (R) oil. Between 7 to 12 data sets were collected to cover full Ewald
spheres to a resolution of better than 0.75 Å. Crystals were held at 100 K
with a Cryostream cooler, mounted to a Bruker APEXII single crystal X-ray
diffractometer, Mo radiation (Bruker 2012), equipped with a fine-focus X-ray
tube, Miracol X-ray optical collimator, and CCD detector. Crystal-to-detector
distance was 40 mm and the exposure times were between 20 to 120 seconds per
frame for all sets, pending on sample size. The scan widths were 0.5°.
Crystal data, data collection, and structure refinement details are summarized
in Table 5. The data were integrated and scaled using SAINT,
SADABS within the APEX2 software package by Bruker (2012). Data work-up
was done with SAINT (Bruker, 2012). Structures were solved with SHELXS
 (Sheldrick, 2008), and refined with SHELXL (Sheldrick 2015).
;
_diffrn_ambient_temperature     100(2)
_diffrn_source     'sealed x-ray tube'
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker APEXII'
_diffrn_measurement_device     'κ-geometry diffractometer'
_diffrn_measurement_method     'φ or ω oscillation scans'
_diffrn_detector     'APEX-II CCD'
_diffrn_reflns_number     21043
_diffrn_reflns_av_R_equivalents     0.0479
_diffrn_reflns_av_unetI/netI     0.0678
_diffrn_reflns_theta_min     1.921
_diffrn_reflns_theta_max     30.78
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.982
_diffrn_measured_fraction_theta_full     1
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -30
_diffrn_reflns_limit_k_max     30
_diffrn_reflns_limit_l_min     -13
_diffrn_reflns_limit_l_max     13
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     ?
_diffrn_radiation_probe     x-ray
_reflns_number_total     7694
_reflns_number_gt     5666
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0787
_refine_ls_R_factor_gt     0.0511
_refine_ls_wR_factor_gt     0.0998
_refine_ls_wR_factor_ref     0.1127
_refine_ls_goodness_of_fit_ref     1.013
_refine_ls_restrained_S_all     1
_refine_ls_number_reflns     7694
_refine_ls_number_parameters     368
_refine_ls_number_restraints     293
_refine_ls_number_constraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0370P)²+0.3946P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0
_refine_diff_density_max     0.51
_refine_diff_density_min     -0.419
_refine_ls_extinction_method     none
_refine_ls_abs_structure_details
;
Flack x determined using 2891 quotients
[(I⁺)-(I⁻)]/[(I⁺)+(I⁻)]
(Parsons et al.,  2013).
;
_refine_ls_abs_structure_Flack     0.03(4)
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'
_computing_data_collection
;
APEX2 (Bruker, 2012)
;
_computing_cell_refinement
;
SAINT (Bruker, 2012)
;
_computing_data_reduction
;
SORTAV (Blessing, 1995)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
WinGX publication routines (Farrugia, 2012)
;
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 0.3234(5) 0.72968(17) 0.0597(4) 0.0242(8) Uani d 1 . .
    C C2 0.2356(5) 0.72153(15) -0.0890(4) 0.0245(7) Uani d 1 . .
    H H2 0.094609 0.710973 -0.119493 0.029 Uiso calc 1 . .
    C C3 0.3544(6) 0.72883(15) -0.1957(4) 0.0233(7) Uani d 1 . .
    H H3 0.295113 0.722886 -0.298681 0.028 Uiso calc 1 . .
    C C4 0.5579(5) 0.74471(18) -0.1494(4) 0.0269(7) Uani d 1 . .
    C C5 0.6459(5) 0.7519(2) 0.0015(4) 0.0333(8) Uani d 1 . .
    H H5 0.787173 0.761973 0.032826 0.04 Uiso calc 1 . .
    C C6 0.5286(5) 0.7444(2) 0.1060(4) 0.0340(8) Uani d 1 . .
    H H6 0.58849 0.749394 0.209183 0.041 Uiso calc 1 . .
    S S1 0.02973(14) 0.74842(5) 0.39257(10) 0.0343(2) Uani d 1 . .
    C C7 0.1630(5) 0.76439(17) 0.2634(4) 0.0278(8) Uani d 1 . .
    O O1 0.2409(4) 0.81978(12) 0.2408(3) 0.0355(6) Uani d 1 . .
    C C8 0.444(2) 0.9025(7) 0.378(3) 0.041(2) Uani d 0.444(4) A 1
    H H8A 0.523678 0.868668 0.436354 0.061 Uiso calc 0.444(4) A 1
    H H8B 0.445317 0.939758 0.441278 0.061 Uiso calc 0.444(4) A 1
    H H8C 0.504598 0.913242 0.293399 0.061 Uiso calc 0.444(4) A 1
    C C9 0.229(2) 0.8810(7) 0.321(2) 0.034(2) Uani d 0.444(4) A 1
    H H9A 0.165251 0.873017 0.408306 0.041 Uiso calc 0.444(4) A 1
    C C10 0.1038(14) 0.9302(4) 0.2216(12) 0.0382(19) Uani d 0.444(4) A 1
    H H10A 0.093609 0.968145 0.282145 0.046 Uiso calc 0.444(4) A 1
    H H10B 0.177813 0.942314 0.143912 0.046 Uiso calc 0.444(4) A 1
    C C11 -0.1086(17) 0.9096(6) 0.1463(15) 0.057(3) Uani d 0.444(4) A 1
    H H11A -0.100617 0.874981 0.077258 0.086 Uiso calc 0.444(4) A 1
    H H11B -0.182427 0.945155 0.090835 0.086 Uiso calc 0.444(4) A 1
    H H11C -0.181371 0.895306 0.221737 0.086 Uiso calc 0.444(4) A 1
    C C8B 0.393(3) 0.9101(8) 0.374(3) 0.041(2) Uani d 0.354(4) A 2
    H H8D 0.368205 0.949443 0.422835 0.061 Uiso calc 0.354(4) A 2
    H H8E 0.426634 0.919652 0.277802 0.061 Uiso calc 0.354(4) A 2
    H H8F 0.508114 0.887578 0.437639 0.061 Uiso calc 0.354(4) A 2
    C C9B 0.204(3) 0.8694(9) 0.349(2) 0.034(3) Uani d 0.354(4) A 2
    H H9B 0.1939 0.848955 0.445096 0.041 Uiso calc 0.354(4) A 2
    C C10B 0.0088(18) 0.9043(5) 0.2850(13) 0.035(2) Uani d 0.354(4) A 2
    H H10C -0.108465 0.875614 0.282587 0.042 Uiso calc 0.354(4) A 2
    H H10D -0.004249 0.939951 0.351796 0.042 Uiso calc 0.354(4) A 2
    C C11B -0.003(2) 0.9293(5) 0.1310(13) 0.039(3) Uani d 0.354(4) A 2
    H H11D -0.131226 0.952741 0.097632 0.058 Uiso calc 0.354(4) A 2
    H H11E 0.001174 0.894153 0.062582 0.058 Uiso calc 0.354(4) A 2
    H H11F 0.113275 0.957498 0.131893 0.058 Uiso calc 0.354(4) A 2
    C C8C 0.366(4) 0.9172(10) 0.333(4) 0.041(2) Uani d 0.202(4) A 3
    H H8G 0.33353 0.955948 0.380465 0.061 Uiso calc 0.202(4) A 3
    H H8H 0.395751 0.927403 0.235543 0.061 Uiso calc 0.202(4) A 3
    H H8I 0.486429 0.897102 0.396154 0.061 Uiso calc 0.202(4) A 3
    C C9C 0.187(4) 0.8727(15) 0.311(5) 0.035(3) Uani d 0.202(4) A 3
    H H9C 0.154489 0.861448 0.408593 0.042 Uiso calc 0.202(4) A 3
    C C10C -0.005(3) 0.8952(9) 0.201(3) 0.036(3) Uani d 0.202(4) A 3
    H H10E 0.026609 0.899442 0.10069 0.043 Uiso calc 0.202(4) A 3
    H H10F -0.113085 0.862847 0.193378 0.043 Uiso calc 0.202(4) A 3
    C C11C -0.083(3) 0.9564(8) 0.243(3) 0.041(4) Uani d 0.202(4) A 3
    H H11G -0.197989 0.970331 0.163991 0.062 Uiso calc 0.202(4) A 3
    H H11H 0.026427 0.98791 0.257494 0.062 Uiso calc 0.202(4) A 3
    H H11I -0.129624 0.951219 0.336395 0.062 Uiso calc 0.202(4) A 3
    C C12 0.6008(6) 0.7513(2) -0.3988(4) 0.0370(9) Uani d 1 . .
    H H12A 0.555585 0.707954 -0.424741 0.055 Uiso calc 1 . .
    H H12B 0.703873 0.763344 -0.454402 0.055 Uiso calc 1 . .
    H H12C 0.483348 0.779874 -0.424448 0.055 Uiso calc 1 . .
    C C13 -0.2448(5) 0.59142(17) 0.4748(4) 0.0265(8) Uani d 1 . .
    C C14 -0.1540(5) 0.59857(18) 0.6239(4) 0.0275(8) Uani d 1 . .
    H H14 -0.011877 0.607781 0.652848 0.033 Uiso calc 1 . .
    C C15 -0.2673(5) 0.59251(17) 0.7318(4) 0.0269(8) Uani d 1 . .
    H H15 -0.204178 0.597542 0.834465 0.032 Uiso calc 1 . .
    C C16 -0.4754(5) 0.57890(15) 0.6877(4) 0.0224(7) Uani d 1 . .
    C C17 -0.5672(5) 0.57305(19) 0.5371(4) 0.0272(7) Uani d 1 . .
    H H17 -0.709852 0.564724 0.507514 0.033 Uiso calc 1 . .
    C C18 -0.4541(5) 0.57916(18) 0.4312(4) 0.0265(8) Uani d 1 . .
    H H18 -0.517786 0.575071 0.328341 0.032 Uiso calc 1 . .
    C C19 -0.0790(5) 0.55447(17) 0.2769(4) 0.0264(8) Uani d 1 . .
    C C20 0.1078(9) 0.4170(3) 0.3247(7) 0.081(2) Uani d 1 . .
    H H20A 0.217303 0.447506 0.323526 0.122 Uiso calc 1 . .
    H H20B 0.140773 0.376905 0.282401 0.122 Uiso calc 1 . .
    H H20C 0.094917 0.410283 0.427702 0.122 Uiso calc 1 . .
    C C21 -0.0908(7) 0.44190(19) 0.2334(6) 0.0484(12) Uani d 1 . .
    H H21 -0.073927 0.452727 0.130872 0.058 Uiso calc 1 . .
    C C22 -0.2657(10) 0.3961(2) 0.2227(6) 0.0655(17) Uani d 1 . .
    H H22A -0.227219 0.355534 0.183068 0.079 Uiso calc 1 . .
    H H22B -0.287127 0.38815 0.324243 0.079 Uiso calc 1 . .
    C C23 -0.4637(10) 0.4183(3) 0.1252(6) 0.0695(18) Uani d 1 . .
    H H23A -0.506915 0.457378 0.166255 0.104 Uiso calc 1 . .
    H H23B -0.569058 0.385928 0.121697 0.104 Uiso calc 1 . .
    H H23C -0.444471 0.426172 0.024169 0.104 Uiso calc 1 . .
    C C24 -0.5110(6) 0.5739(2) 0.9395(4) 0.0342(8) Uani d 1 . .
    H H24A -0.401411 0.5425 0.965042 0.051 Uiso calc 1 . .
    H H24B -0.615316 0.565495 0.996758 0.051 Uiso calc 1 . .
    H H24C -0.453949 0.616142 0.96361 0.051 Uiso calc 1 . .
    N N1 0.2009(5) 0.72059(15) 0.1684(3) 0.0284(7) Uani d 1 . .
    H H1N 0.157(6) 0.684(2) 0.170(5) 0.034 Uiso d 1 . .
    N N2 -0.1264(5) 0.59976(16) 0.3643(3) 0.0286(7) Uani d 1 . .
    H H2N -0.084(6) 0.637(2) 0.354(4) 0.034 Uiso d 1 . .
    O O2 0.6872(3) 0.75506(13) -0.2435(3) 0.0330(6) Uani d 1 . .
    O O3 -0.1487(4) 0.49852(11) 0.3056(3) 0.0317(6) Uani d 1 . .
    O O4 -0.6018(4) 0.57030(13) 0.7839(3) 0.0295(5) Uani d 1 . .
    S S2 0.05382(13) 0.56943(4) 0.14638(10) 0.0289(2) Uani d 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 . 1.373(5) ?
    C1 C6 . 1.380(5) ?
    C1 N1 . 1.440(4) ?
    C2 C3 . 1.402(5) ?
    C2 H2 . 0.95 ?
    C3 C4 . 1.376(5) ?
    C3 H3 . 0.95 ?
    C4 O2 . 1.371(4) ?
    C4 C5 . 1.390(5) ?
    C5 C6 . 1.378(5) ?
    C5 H5 . 0.95 ?
    C6 H6 . 0.95 ?
    S1 C7 . 1.671(4) ?
    C7 O1 . 1.320(4) ?
    C7 N1 . 1.337(4) ?
    O1 C9C . 1.38(4) ?
    O1 C9B . 1.50(2) ?
    O1 C9 . 1.51(2) ?
    C8 C9 . 1.490(13) ?
    C8 H8A . 0.98 ?
    C8 H8B . 0.98 ?
    C8 H8C . 0.98 ?
    C9 C10 . 1.512(14) ?
    C9 H9A . 1 ?
    C10 C11 . 1.501(13) ?
    C10 H10A . 0.99 ?
    C10 H10B . 0.99 ?
    C11 H11A . 0.98 ?
    C11 H11B . 0.98 ?
    C11 H11C . 0.98 ?
    C8B C9B . 1.508(16) ?
    C8B H8D . 0.98 ?
    C8B H8E . 0.98 ?
    C8B H8F . 0.98 ?
    C9B C10B . 1.504(16) ?
    C9B H9B . 1 ?
    C10B C11B . 1.497(13) ?
    C10B H10C . 0.99 ?
    C10B H10D . 0.99 ?
    C11B H11D . 0.98 ?
    C11B H11E . 0.98 ?
    C11B H11F . 0.98 ?
    C8C C9C . 1.51(2) ?
    C8C H8G . 0.98 ?
    C8C H8H . 0.98 ?
    C8C H8I . 0.98 ?
    C9C C10C . 1.52(2) ?
    C9C H9C . 1 ?
    C10C C11C . 1.486(18) ?
    C10C H10E . 0.99 ?
    C10C H10F . 0.99 ?
    C11C H11G . 0.98 ?
    C11C H11H . 0.98 ?
    C11C H11I . 0.98 ?
    C12 O2 . 1.417(4) ?
    C12 H12A . 0.98 ?
    C12 H12B . 0.98 ?
    C12 H12C . 0.98 ?
    C13 C14 . 1.378(5) ?
    C13 C18 . 1.394(5) ?
    C13 N2 . 1.432(4) ?
    C14 C15 . 1.382(5) ?
    C14 H14 . 0.95 ?
    C15 C16 . 1.392(5) ?
    C15 H15 . 0.95 ?
    C16 O4 . 1.365(4) ?
    C16 C17 . 1.389(5) ?
    C17 C18 . 1.366(5) ?
    C17 H17 . 0.95 ?
    C18 H18 . 0.95 ?
    C19 O3 . 1.323(4) ?
    C19 N2 . 1.335(4) ?
    C19 S2 . 1.674(4) ?
    C20 C21 . 1.502(7) ?
    C20 H20A . 0.98 ?
    C20 H20B . 0.98 ?
    C20 H20C . 0.98 ?
    C21 O3 . 1.466(5) ?
    C21 C22 . 1.508(7) ?
    C21 H21 . 1 ?
    C22 C23 . 1.501(8) ?
    C22 H22A . 0.99 ?
    C22 H22B . 0.99 ?
    C23 H23A . 0.98 ?
    C23 H23B . 0.98 ?
    C23 H23C . 0.98 ?
    C24 O4 . 1.426(4) ?
    C24 H24A . 0.98 ?
    C24 H24B . 0.98 ?
    C24 H24C . 0.98 ?
    N1 H1N . 0.82(4) ?
    N2 H2N . 0.86(4) ?
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 . . 120.8(3) ?
    C2 C1 N1 . . 119.3(3) ?
    C6 C1 N1 . . 119.9(3) ?
    C1 C2 C3 . . 119.9(3) ?
    C1 C2 H2 . . 120.1 ?
    C3 C2 H2 . . 120.1 ?
    C4 C3 C2 . . 119.2(3) ?
    C4 C3 H3 . . 120.4 ?
    C2 C3 H3 . . 120.4 ?
    O2 C4 C3 . . 124.5(3) ?
    O2 C4 C5 . . 115.2(3) ?
    C3 C4 C5 . . 120.4(3) ?
    C6 C5 C4 . . 120.1(3) ?
    C6 C5 H5 . . 119.9 ?
    C4 C5 H5 . . 119.9 ?
    C5 C6 C1 . . 119.6(3) ?
    C5 C6 H6 . . 120.2 ?
    C1 C6 H6 . . 120.2 ?
    O1 C7 N1 . . 112.1(3) ?
    O1 C7 S1 . . 125.7(3) ?
    N1 C7 S1 . . 122.1(3) ?
    C7 O1 C9C . . 119.8(15) ?
    C7 O1 C9B . . 112.9(7) ?
    C7 O1 C9 . . 128.6(7) ?
    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 ?
    C8 C9 O1 . . 106.4(12) ?
    C8 C9 C10 . . 111.3(12) ?
    O1 C9 C10 . . 112.3(12) ?
    C8 C9 H9A . . 108.9 ?
    O1 C9 H9A . . 108.9 ?
    C10 C9 H9A . . 108.9 ?
    C11 C10 C9 . . 114.8(10) ?
    C11 C10 H10A . . 108.6 ?
    C9 C10 H10A . . 108.6 ?
    C11 C10 H10B . . 108.6 ?
    C9 C10 H10B . . 108.6 ?
    H10A C10 H10B . . 107.5 ?
    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 ?
    C9B C8B H8D . . 109.5 ?
    C9B C8B H8E . . 109.5 ?
    H8D C8B H8E . . 109.5 ?
    C9B C8B H8F . . 109.5 ?
    H8D C8B H8F . . 109.5 ?
    H8E C8B H8F . . 109.5 ?
    C10B C9B O1 . . 110.0(12) ?
    C10B C9B C8B . . 114.0(14) ?
    O1 C9B C8B . . 104.2(14) ?
    C10B C9B H9B . . 109.5 ?
    O1 C9B H9B . . 109.5 ?
    C8B C9B H9B . . 109.5 ?
    C11B C10B C9B . . 113.7(11) ?
    C11B C10B H10C . . 108.8 ?
    C9B C10B H10C . . 108.8 ?
    C11B C10B H10D . . 108.8 ?
    C9B C10B H10D . . 108.8 ?
    H10C C10B H10D . . 107.7 ?
    C10B C11B H11D . . 109.5 ?
    C10B C11B H11E . . 109.5 ?
    H11D C11B H11E . . 109.5 ?
    C10B C11B H11F . . 109.5 ?
    H11D C11B H11F . . 109.5 ?
    H11E C11B H11F . . 109.5 ?
    C9C C8C H8G . . 109.5 ?
    C9C C8C H8H . . 109.5 ?
    H8G C8C H8H . . 109.5 ?
    C9C C8C H8I . . 109.5 ?
    H8G C8C H8I . . 109.5 ?
    H8H C8C H8I . . 109.5 ?
    O1 C9C C8C . . 107(3) ?
    O1 C9C C10C . . 102(2) ?
    C8C C9C C10C . . 115(2) ?
    O1 C9C H9C . . 110.8 ?
    C8C C9C H9C . . 110.8 ?
    C10C C9C H9C . . 110.8 ?
    C11C C10C C9C . . 113(2) ?
    C11C C10C H10E . . 109 ?
    C9C C10C H10E . . 109 ?
    C11C C10C H10F . . 109 ?
    C9C C10C H10F . . 109 ?
    H10E C10C H10F . . 107.8 ?
    C10C C11C H11G . . 109.5 ?
    C10C C11C H11H . . 109.5 ?
    H11G C11C H11H . . 109.5 ?
    C10C C11C H11I . . 109.5 ?
    H11G C11C H11I . . 109.5 ?
    H11H C11C H11I . . 109.5 ?
    O2 C12 H12A . . 109.5 ?
    O2 C12 H12B . . 109.5 ?
    H12A C12 H12B . . 109.5 ?
    O2 C12 H12C . . 109.5 ?
    H12A C12 H12C . . 109.5 ?
    H12B C12 H12C . . 109.5 ?
    C14 C13 C18 . . 120.0(3) ?
    C14 C13 N2 . . 120.0(3) ?
    C18 C13 N2 . . 119.9(3) ?
    C13 C14 C15 . . 120.8(3) ?
    C13 C14 H14 . . 119.6 ?
    C15 C14 H14 . . 119.6 ?
    C14 C15 C16 . . 118.9(3) ?
    C14 C15 H15 . . 120.5 ?
    C16 C15 H15 . . 120.5 ?
    O4 C16 C17 . . 115.6(3) ?
    O4 C16 C15 . . 124.3(3) ?
    C17 C16 C15 . . 120.1(3) ?
    C18 C17 C16 . . 120.6(3) ?
    C18 C17 H17 . . 119.7 ?
    C16 C17 H17 . . 119.7 ?
    C17 C18 C13 . . 119.6(3) ?
    C17 C18 H18 . . 120.2 ?
    C13 C18 H18 . . 120.2 ?
    O3 C19 N2 . . 112.5(3) ?
    O3 C19 S2 . . 125.5(3) ?
    N2 C19 S2 . . 122.0(3) ?
    C21 C20 H20A . . 109.5 ?
    C21 C20 H20B . . 109.5 ?
    H20A C20 H20B . . 109.5 ?
    C21 C20 H20C . . 109.5 ?
    H20A C20 H20C . . 109.5 ?
    H20B C20 H20C . . 109.5 ?
    O3 C21 C20 . . 109.0(4) ?
    O3 C21 C22 . . 106.1(3) ?
    C20 C21 C22 . . 112.8(4) ?
    O3 C21 H21 . . 109.6 ?
    C20 C21 H21 . . 109.6 ?
    C22 C21 H21 . . 109.6 ?
    C23 C22 C21 . . 114.0(4) ?
    C23 C22 H22A . . 108.8 ?
    C21 C22 H22A . . 108.8 ?
    C23 C22 H22B . . 108.8 ?
    C21 C22 H22B . . 108.8 ?
    H22A C22 H22B . . 107.6 ?
    C22 C23 H23A . . 109.5 ?
    C22 C23 H23B . . 109.5 ?
    H23A C23 H23B . . 109.5 ?
    C22 C23 H23C . . 109.5 ?
    H23A C23 H23C . . 109.5 ?
    H23B C23 H23C . . 109.5 ?
    O4 C24 H24A . . 109.5 ?
    O4 C24 H24B . . 109.5 ?
    H24A C24 H24B . . 109.5 ?
    O4 C24 H24C . . 109.5 ?
    H24A C24 H24C . . 109.5 ?
    H24B C24 H24C . . 109.5 ?
    C7 N1 C1 . . 125.5(3) ?
    C7 N1 H1N . . 121(3) ?
    C1 N1 H1N . . 113(3) ?
    C19 N2 C13 . . 125.6(3) ?
    C19 N2 H2N . . 119(3) ?
    C13 N2 H2N . . 116(3) ?
    C4 O2 C12 . . 116.9(3) ?
    C19 O3 C21 . . 120.2(3) ?
    C16 O4 C24 . . 117.1(3) ?
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 H1N S2 . 0.82(4) 2.53(4) 3.347(3) 171(4) yes
    N2 H2N S1 . 0.86(4) 2.47(4) 3.314(3) 165(4) yes
    C12 H12B S1 1_654 0.98 2.86 3.793(4) 158.3 yes
    C24 H24B S2 1_456 0.98 2.86 3.819(4) 167.2 yes
    C18 H18 S2 1_455 0.95 2.98 3.730(4) 136.3 yes
    C10B H10C S1 . 0.99 2.96 3.445(11) 111.5 yes
_shelx_estimated_absorpt_T_min     0.869
_shelx_estimated_absorpt_T_max     0.953
data_III
_audit_creation_method     'WinGX routine CIF_UPDATE'
_audit_conform_dict_name     cif_core.dic
_audit_conform_dict_version     2.4.5
_chemical_name_systematic
;
(S)-2-Butyl N-(4-fluorophenyl)thiocarbamate
;
_chemical_formula_moiety     'C11 H14 F N O S'
_chemical_formula_sum     'C11 H14 F N O S'
_chemical_formula_iupac     'C11 H14 F N O S'
_chemical_formula_weight     227.29
_chemical_absolute_configuration     rmad
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21'
_symmetry_space_group_name_Hall     'P 2yb'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z'
_cell_length_a     6.9723(13)
_cell_length_b     20.166(3)
_cell_length_c     8.2818(14)
_cell_angle_alpha     90
_cell_angle_beta     99.403(13)
_cell_angle_gamma     90
_cell_volume     1148.8(3)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     1312
_cell_measurement_theta_min     2.69
_cell_measurement_theta_max     18.89
_cell_measurement_temperature     100(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.5
_exptl_crystal_size_mid     0.1
_exptl_crystal_size_min     0.05
_exptl_crystal_density_diffrn     1.314
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     480
loop_
    _exptl_crystal_face_index_h
    _exptl_crystal_face_index_k
    _exptl_crystal_face_index_l
    _exptl_crystal_face_perp_dist
    0 -1 -1 0.0250
    1 0 0 0.2110
    -1 0 0 0.2910
    0 1 -3 0.0410
    0 -1 1 0.0250
    0 1 1 0.0200
    0 -1 3 0.0290
_exptl_absorpt_coefficient_mu     0.268
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_absorpt_correction_T_min     0.863
_exptl_absorpt_correction_T_max     1
_exptl_special_details
;
Crystals were mounted on a CryoloopTM (0.2--0.3mm, Hampton Research) with
Paratone (R) oil. Between 7 to 12 data sets were collected to cover full Ewald
spheres to a resolution of better than 0.75 Å. Crystals were held at 100 K
with a Cryostream cooler, mounted to a Bruker APEXII single crystal X-ray
diffractometer, Mo radiation (Bruker 2012), equipped with a fine-focus X-ray
tube, Miracol X-ray optical collimator, and CCD detector. Crystal-to-detector
distance was 40 mm and the exposure times were between 20 to 120 seconds per
frame for all sets, pending on sample size. The scan widths were 0.5°.
Crystal data, data collection, and structure refinement details are summarized
in Table 5. The data were integrated and scaled using SAINT,
SADABS within the APEX2 software package by Bruker (2012). Data work-up
was done with SAINT (Bruker, 2012). Structures were solved with SHELXS
 (Sheldrick, 2008), and refined with SHELXL (Sheldrick 2015).
;
_diffrn_ambient_temperature     100(2)
_diffrn_source     'sealed x-ray tube'
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker APEXII'
_diffrn_measurement_device     'κ-geometry diffractometer'
_diffrn_measurement_method     'φ or ω oscillation scans'
_diffrn_detector     'APEXII CCD'
_diffrn_reflns_number     10466
_diffrn_reflns_av_R_equivalents     0.1705
_diffrn_reflns_av_unetI/netI     0.2243
_diffrn_reflns_theta_min     2.02
_diffrn_reflns_theta_max     27.5
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     1
_diffrn_measured_fraction_theta_full     1
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -26
_diffrn_reflns_limit_k_max     26
_diffrn_reflns_limit_l_min     -10
_diffrn_reflns_limit_l_max     10
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     ?
_diffrn_radiation_probe     x-ray
_reflns_number_total     5263
_reflns_number_gt     2448
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1842
_refine_ls_R_factor_gt     0.0677
_refine_ls_wR_factor_gt     0.1089
_refine_ls_wR_factor_ref     0.1432
_refine_ls_goodness_of_fit_ref     0.946
_refine_ls_restrained_S_all     0.946
_refine_ls_number_reflns     5263
_refine_ls_number_parameters     257
_refine_ls_number_restraints     2
_refine_ls_number_constraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                      'w=1/[σ²(Fo²)+(0.0402P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0
_refine_ls_shift/su_mean     0
_refine_diff_density_max     0.451
_refine_diff_density_min     -0.519
_refine_ls_extinction_method     none
_refine_ls_abs_structure_details
;
Flack x determined using 2891 quotients
[(I⁺)-(I⁻)]/[(I⁺)+(I⁻)]
(Parsons et al.,  2013).
;
_refine_ls_abs_structure_Flack     0.17(13)
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'
    F F 0.0171 0.0103 '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'
_computing_data_collection
;
APEX2 (Bruker, 2012)
;
_computing_cell_refinement
;
SAINT (Bruker, 2012)
;
_computing_data_reduction
;
SORTAV (Blessing, 1995)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
WinGX publication routines (Farrugia, 2012)
;
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 0.8966(7) 0.6722(3) 0.5978(6) 0.021(2) Uani d 1 . .
    C C2 1.0905(8) 0.6846(3) 0.6605(5) 0.023(2) Uani d 1 . .
    H H2 1.130829 0.688684 0.775314 0.028 Uiso calc 1 . .
    C C3 1.2256(6) 0.6911(3) 0.5552(7) 0.024(2) Uani d 1 . .
    H H3 1.35816 0.699572 0.598067 0.029 Uiso calc 1 . .
    C C4 1.1666(7) 0.6852(4) 0.3872(6) 0.023(2) Uani d 1 . .
    C C5 0.9726(8) 0.6727(3) 0.3245(5) 0.022(2) Uani d 1 . .
    H H5 0.932364 0.66869 0.209695 0.027 Uiso calc 1 . .
    C C6 0.8376(6) 0.6663(3) 0.4298(7) 0.022(2) Uani d 1 . .
    H H6 0.70503 0.657801 0.386939 0.027 Uiso calc 1 . .
    C C7 0.7286(12) 0.6991(4) 0.8282(12) 0.019(2) Uani d 1 . .
    C C8 1.0523(12) 0.8141(4) 1.0396(12) 0.032(3) Uani d 1 . .
    H H8A 1.116505 0.772014 1.073864 0.048 Uiso calc 1 . .
    H H8B 1.065696 0.84452 1.133121 0.048 Uiso calc 1 . .
    H H8C 1.112971 0.833823 0.952221 0.048 Uiso calc 1 . .
    C C9 0.8394(12) 0.8018(4) 0.9774(11) 0.019(2) Uani d 1 . .
    H H9 0.775524 0.782224 1.06603 0.023 Uiso calc 1 . .
    C C10 0.7329(12) 0.8630(4) 0.9100(11) 0.025(2) Uani d 1 . .
    H H10A 0.801429 0.881895 0.824864 0.03 Uiso calc 1 . .
    H H10B 0.740265 0.896099 0.999075 0.03 Uiso calc 1 . .
    C C11 0.5181(11) 0.8534(4) 0.8352(12) 0.034(3) Uani d 1 . .
    H H11A 0.50897 0.826147 0.736278 0.051 Uiso calc 1 . .
    H H11B 0.458106 0.896705 0.80698 0.051 Uiso calc 1 . .
    H H11C 0.450137 0.831193 0.914735 0.051 Uiso calc 1 . .
    C C12 0.1978(7) 0.5306(3) 0.9155(6) 0.019(2) Uani d 1 . .
    C C13 0.0041(8) 0.5172(3) 0.8542(5) 0.023(2) Uani d 1 . .
    H H13 -0.036579 0.511975 0.739728 0.027 Uiso calc 1 . .
    C C14 -0.1301(6) 0.5113(3) 0.9604(7) 0.023(2) Uani d 1 . .
    H H14 -0.262522 0.502042 0.918484 0.028 Uiso calc 1 . .
    C C15 -0.0706(8) 0.5188(3) 1.1279(7) 0.023(2) Uani d 1 . .
    C C16 0.1231(9) 0.5323(3) 1.1892(5) 0.025(2) Uani d 1 . .
    H H16 0.163773 0.537508 1.303733 0.029 Uiso calc 1 . .
    C C17 0.2573(6) 0.5382(3) 1.0831(7) 0.021(2) Uani d 1 . .
    H H17 0.38972 0.547441 1.124978 0.026 Uiso calc 1 . .
    C C18 0.3719(11) 0.5013(4) 0.6901(11) 0.014(2) Uani d 1 . .
    C C19 0.4944(12) 0.3531(4) 0.6560(11) 0.028(2) Uani d 1 . .
    H H19A 0.605381 0.383457 0.678678 0.042 Uiso calc 1 . .
    H H19B 0.5244 0.317553 0.583497 0.042 Uiso calc 1 . .
    H H19C 0.468179 0.333968 0.758962 0.042 Uiso calc 1 . .
    C C20 0.3174(12) 0.3908(4) 0.5742(11) 0.023(2) Uani d 1 . .
    H H20 0.344348 0.410563 0.469454 0.028 Uiso calc 1 . .
    C C21 0.1363(12) 0.3495(4) 0.5410(11) 0.026(2) Uani d 1 . .
    H H21A 0.112572 0.330173 0.645849 0.031 Uiso calc 1 . .
    H H21B 0.160071 0.312194 0.468958 0.031 Uiso calc 1 . .
    C C22 -0.0480(12) 0.3853(4) 0.4618(12) 0.031(3) Uani d 1 . .
    H H22A -0.080503 0.419931 0.535926 0.047 Uiso calc 1 . .
    H H22B -0.155415 0.353511 0.440115 0.047 Uiso calc 1 . .
    H H22C -0.0265 0.40553 0.358697 0.047 Uiso calc 1 . .
    N N1 0.7567(10) 0.6619(4) 0.7012(9) 0.0215(19) Uani d 1 . .
    N N2 0.3377(10) 0.5404(3) 0.8108(9) 0.0188(18) Uani d 1 . .
    O O1 0.8371(7) 0.7537(3) 0.8418(7) 0.0201(14) Uani d 1 . .
    O O2 0.2729(8) 0.4444(3) 0.6850(7) 0.0220(15) Uani d 1 . .
    F F1 1.2980(7) 0.6908(2) 0.2885(7) 0.0307(14) Uani d 1 . .
    F F2 -0.2026(7) 0.5147(3) 1.2271(7) 0.0310(13) Uani d 1 . .
    S S1 0.5732(3) 0.67758(11) 0.9542(3) 0.0232(6) Uani d 1 . .
    S S2 0.5266(3) 0.52266(12) 0.5636(3) 0.0237(6) Uani d 1 . .
    H H1N 0.682(11) 0.628(3) 0.681(10) 0.028 Uiso d 1 . .
    H H2N 0.384(10) 0.580(3) 0.832(10) 0.028 Uiso d 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 . 1.39 ?
    C1 C6 . 1.39 ?
    C1 N1 . 1.414(8) ?
    C2 C3 . 1.39 ?
    C2 H2 . 0.95 ?
    C3 C4 . 1.39 ?
    C3 H3 . 0.95 ?
    C4 F1 . 1.329(6) ?
    C4 C5 . 1.39 ?
    C5 C6 . 1.39 ?
    C5 H5 . 0.95 ?
    C6 H6 . 0.95 ?
    C7 O1 . 1.329(9) ?
    C7 N1 . 1.332(11) ?
    C7 S1 . 1.680(9) ?
    C8 C9 . 1.510(10) ?
    C8 H8A . 0.98 ?
    C8 H8B . 0.98 ?
    C8 H8C . 0.98 ?
    C9 O1 . 1.483(10) ?
    C9 C10 . 1.500(11) ?
    C9 H9 . 1 ?
    C10 C11 . 1.536(10) ?
    C10 H10A . 0.99 ?
    C10 H10B . 0.99 ?
    C11 H11A . 0.98 ?
    C11 H11B . 0.98 ?
    C11 H11C . 0.98 ?
    C12 C13 . 1.39 ?
    C12 C17 . 1.39 ?
    C12 N2 . 1.421(8) ?
    C13 C14 . 1.39 ?
    C13 H13 . 0.95 ?
    C14 C15 . 1.39 ?
    C14 H14 . 0.95 ?
    C15 F2 . 1.333(6) ?
    C15 C16 . 1.39 ?
    C16 C17 . 1.39 ?
    C16 H16 . 0.95 ?
    C17 H17 . 0.95 ?
    C18 N2 . 1.325(10) ?
    C18 O2 . 1.335(9) ?
    C18 S2 . 1.678(9) ?
    C19 C20 . 1.512(10) ?
    C19 H19A . 0.98 ?
    C19 H19B . 0.98 ?
    C19 H19C . 0.98 ?
    C20 O2 . 1.483(10) ?
    C20 C21 . 1.501(11) ?
    C20 H20 . 1 ?
    C21 C22 . 1.526(11) ?
    C21 H21A . 0.99 ?
    C21 H21B . 0.99 ?
    C22 H22A . 0.98 ?
    C22 H22B . 0.98 ?
    C22 H22C . 0.98 ?
    N1 H1N . 0.86(5) ?
    N2 H2N . 0.86(5) ?
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 . . 120 ?
    C2 C1 N1 . . 121.7(5) ?
    C6 C1 N1 . . 118.2(5) ?
    C1 C2 C3 . . 120 ?
    C1 C2 H2 . . 120 ?
    C3 C2 H2 . . 120 ?
    C4 C3 C2 . . 120 ?
    C4 C3 H3 . . 120 ?
    C2 C3 H3 . . 120 ?
    F1 C4 C5 . . 120.8(5) ?
    F1 C4 C3 . . 119.2(5) ?
    C5 C4 C3 . . 120 ?
    C6 C5 C4 . . 120 ?
    C6 C5 H5 . . 120 ?
    C4 C5 H5 . . 120 ?
    C5 C6 C1 . . 120 ?
    C5 C6 H6 . . 120 ?
    C1 C6 H6 . . 120 ?
    O1 C7 N1 . . 112.2(8) ?
    O1 C7 S1 . . 125.2(7) ?
    N1 C7 S1 . . 122.5(7) ?
    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 C10 . . 108.2(7) ?
    O1 C9 C8 . . 104.7(7) ?
    C10 C9 C8 . . 113.0(7) ?
    O1 C9 H9 . . 110.2 ?
    C10 C9 H9 . . 110.2 ?
    C8 C9 H9 . . 110.2 ?
    C9 C10 C11 . . 115.9(7) ?
    C9 C10 H10A . . 108.3 ?
    C11 C10 H10A . . 108.3 ?
    C9 C10 H10B . . 108.3 ?
    C11 C10 H10B . . 108.3 ?
    H10A C10 H10B . . 107.4 ?
    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 . . 120 ?
    C13 C12 N2 . . 121.8(5) ?
    C17 C12 N2 . . 118.1(5) ?
    C14 C13 C12 . . 120 ?
    C14 C13 H13 . . 120 ?
    C12 C13 H13 . . 120 ?
    C13 C14 C15 . . 120 ?
    C13 C14 H14 . . 120 ?
    C15 C14 H14 . . 120 ?
    F2 C15 C16 . . 121.0(5) ?
    F2 C15 C14 . . 119.0(5) ?
    C16 C15 C14 . . 120 ?
    C15 C16 C17 . . 120 ?
    C15 C16 H16 . . 120 ?
    C17 C16 H16 . . 120 ?
    C16 C17 C12 . . 120 ?
    C16 C17 H17 . . 120 ?
    C12 C17 H17 . . 120 ?
    N2 C18 O2 . . 112.3(7) ?
    N2 C18 S2 . . 122.1(6) ?
    O2 C18 S2 . . 125.6(7) ?
    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 C21 . . 105.3(7) ?
    O2 C20 C19 . . 109.1(7) ?
    C21 C20 C19 . . 113.8(8) ?
    O2 C20 H20 . . 109.5 ?
    C21 C20 H20 . . 109.5 ?
    C19 C20 H20 . . 109.5 ?
    C20 C21 C22 . . 116.1(7) ?
    C20 C21 H21A . . 108.3 ?
    C22 C21 H21A . . 108.3 ?
    C20 C21 H21B . . 108.3 ?
    C22 C21 H21B . . 108.3 ?
    H21A C21 H21B . . 107.4 ?
    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 . . 126.9(7) ?
    C7 N1 H1N . . 116(6) ?
    C1 N1 H1N . . 117(6) ?
    C18 N2 C12 . . 127.2(7) ?
    C18 N2 H2N . . 126(6) ?
    C12 N2 H2N . . 106(6) ?
    C7 O1 C9 . . 122.8(7) ?
    C18 O2 C20 . . 119.1(7) ?
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 H1N S2 . 0.86(5) 2.51(5) 3.341(8) 164(8) yes
    N2 H2N S1 . 0.86(5) 2.50(5) 3.336(7) 165(7) yes
    C8 H8A F1 1_556 0.98 2.59 3.494(10) 153.5 yes
_shelx_estimated_absorpt_T_min     0.877
_shelx_estimated_absorpt_T_max     0.987
data_IV
_audit_creation_method     'WinGX routine CIF_UPDATE'
_audit_conform_dict_name     cif_core.dic
_audit_conform_dict_version     2.4.5
_chemical_name_systematic
;
(S)-2-Butyl N-(4-chlorophenyl)thiocarbamate
;
_chemical_formula_moiety     'C11 H14 Cl N O S'
_chemical_formula_sum     'C11 H14 Cl N O S'
_chemical_formula_iupac     'C11 H14 Cl N O S'
_chemical_formula_weight     243.74
_chemical_absolute_configuration     rmad
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21'
_symmetry_space_group_name_Hall     'P 2yb'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z'
_cell_length_a     15.4173(15)
_cell_length_b     5.0170(5)
_cell_length_c     16.2502(15)
_cell_angle_alpha     90
_cell_angle_beta     105.592(5)
_cell_angle_gamma     90
_cell_volume     1210.7(2)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     9275
_cell_measurement_theta_min     2.6
_cell_measurement_theta_max     33.09
_cell_measurement_temperature     100(2)
_exptl_crystal_description     prsm
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.6
_exptl_crystal_size_mid     0.12
_exptl_crystal_size_min     0.11
_exptl_crystal_density_diffrn     1.337
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     512
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
_exptl_absorpt_coefficient_mu     0.462
_exptl_absorpt_correction_type     numerical
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_absorpt_correction_T_min     0.954
_exptl_absorpt_correction_T_max     1
_exptl_special_details
;
Crystals were mounted on a CryoloopTM (0.2--0.3mm, Hampton Research) with
Paratone (R) oil. Between 7 to 12 data sets were collected to cover full Ewald
spheres to a resolution of better than 0.75 Å. Crystals were held at 100 K
with a Cryostream cooler, mounted to a Bruker APEXII single crystal X-ray
diffractometer, Mo radiation (Bruker 2012), equipped with a fine-focus X-ray
tube, Miracol X-ray optical collimator, and CCD detector. Crystal-to-detector
distance was 40 mm and the exposure times were between 20 to 120 seconds per
frame for all sets, pending on sample size. The scan widths were 0.5°.
Crystal data, data collection, and structure refinement details are summarized
in Table 5. The data were integrated and scaled using SAINT,
SADABS within the APEX2 software package by Bruker (2012). Data work-up
was done with SAINT (Bruker, 2012). Structures were solved with SHELXS
 (Sheldrick, 2008), and refined with SHELXL (Sheldrick 2015).
;
_diffrn_ambient_temperature     100(2)
_diffrn_source     'sealed x-ray tube'
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker APEXII'
_diffrn_measurement_device     'κ-geometry diffractometer'
_diffrn_measurement_method     'φ or ω oscillation scans'
_diffrn_detector     'APEX-II CCD'
_diffrn_reflns_number     46534
_diffrn_reflns_av_R_equivalents     0.0294
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_theta_min     2.129
_diffrn_reflns_theta_max     33.298
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.997
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -23
_diffrn_reflns_limit_h_max     23
_diffrn_reflns_limit_k_min     -7
_diffrn_reflns_limit_k_max     7
_diffrn_reflns_limit_l_min     -24
_diffrn_reflns_limit_l_max     25
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     ?
_diffrn_radiation_probe     x-ray
_reflns_number_total     9292
_reflns_number_gt     8469
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0332
_refine_ls_R_factor_gt     0.0272
_refine_ls_wR_factor_gt     0.0631
_refine_ls_wR_factor_ref     0.0663
_refine_ls_goodness_of_fit_ref     1.039
_refine_ls_restrained_S_all     1.039
_refine_ls_number_reflns     9292
_refine_ls_number_parameters     281
_refine_ls_number_restraints     1
_refine_ls_number_constraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0312P)²+0.1769P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0
_refine_diff_density_max     0.363
_refine_diff_density_min     -0.221
_refine_ls_extinction_method     none
_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)
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'
_computing_data_collection
;
APEX2 (Bruker, 2012)
;
_computing_cell_refinement
;
SAINT (Bruker, 2012)
;
_computing_data_reduction
;
SORTAV (Blessing, 1995)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
WinGX publication routines (Farrugia, 2012)
;
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 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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_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_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
_shelx_estimated_absorpt_T_min     0.769
_shelx_estimated_absorpt_T_max     0.951
data_New_Global_Publ_Block
_journal_data_validation_number     ?
_journal_date_recd_electronic     2023-03-06
_journal_date_accepted     2023-03-17
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2023
_journal_volume     79
_journal_issue      4
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     GO
_journal_paper_doi     10.1107/S2056989023002591
_journal_coeditor_code     ZL5044
_publ_contact_author_name     'Dr habil Werner Kaminsky'
_publ_contact_author_address
;
Department of Chemistry
University of Washington
Seattle
Washington, 98195, USA
;
_publ_contact_author_email     'kaminsky@chem.washington.edu'
_publ_contact_author_fax     ?
_publ_contact_author_phone     '206 543 7585'
_publ_section_title
;
Enantiopure (S)-butan-2-yl N-(4 - x-phenyl)thiocarbamates,
x = NO₂, OCH₃, F, and Cl
;
_publ_section_title_footnote     .
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Kaminsky, Werner' .
;
Department of Chemistry Univ. of Washington Seattle, WA 98195
USA
;
    'Kaganyuk, Max' .
;
Department of Chemistry Univ. of Washington Seattle, WA 98195
USA
;
_publ_section_synopsis
;
Enantiopure (S)-butan-2-yl-N-(4 - x-phenyl)thiocarbamates,
x = NO₂, OCH₃, F, and Cl were synthesized from reacting aryl
isothiocyanate with (S)-2-butanol to form new chiral crystals as the
basis for future research into their non-linear physical and potentially
biological properties.
;
