Enanti-opure (<i>S</i>)-butan-2-yl <i>N</i>-(4-<i>x</i>-phen-yl)thio-carbamates, <i>x</i> = NO<sub>2</sub>, OCH<sub>3</sub>, F, and Cl.
Kaminsky, Werner; Kaganyuk, Max; Acta crystallographica. Section E, Crystallographic communications 79 (2023) 386–391; doi:10.1107/S2056989023002591

data_2022729
_publ_section_title
;
 Enanti-opure (<i>S</i>)-butan-2-yl
 <i>N</i>-(4-<i>x</i>-phen-yl)thio-carbamates, <i>x</i> = NO<sub>2</sub>,
 OCH<sub>3</sub>, 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 N2 O3 S'
_chemical_formula_moiety         'C11 H14 N2 O3 S'
_chemical_formula_sum            'C11 H14 N2 O3 S'
_chemical_formula_weight         254.3
_chemical_name_systematic
;
(<i>S</i>)-2-Butyl <i>N</i>-(4-nitrophenyl)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                 101.702(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.052(2)
_cell_length_b                   4.7635(6)
_cell_length_c                   16.853(2)
_cell_measurement_reflns_used    8016
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.26
_cell_measurement_theta_min      2.47
_cell_volume                     1261.9(3)
_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
;
<i>SHELXL2018/3</i> (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 0.993
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       '\f or \w 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  0.0467
_diffrn_reflns_av_unetI/netI     0.0516
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            37641
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.274
_diffrn_reflns_theta_min         1.598
_diffrn_source                   'sealed x-ray tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.255
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.959
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
(SADABS; Krause <i>et al.</i>,  2015)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.122
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.283
_refine_ls_abs_structure_details
;
Flack <i>x</i> determined using 2891 quotients
[(<i>I</i>^+^)-(<i>I</i>^-^)]/[(<i>I</i>^+^)+(<i>I</i>^-^)]
(Parsons <i>et al.</i>,  2013).
;
_refine_ls_abs_structure_Flack   -0.02(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.01
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     317
_refine_ls_number_reflns         9553
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.01
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0387
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0311P)^2^+0.2393P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0761
_refine_ls_wR_factor_ref         0.0844
_reflns_number_gt                7648
_reflns_number_total             9553
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            zl5044sup1.cif
_cod_data_source_block           I
_cod_depositor_comments
'Adding full bibliography for 2022729--2022732.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2022729
_cod_database_fobs_code          2022729
_shelx_estimated_absorpt_t_min   0.862
_shelx_estimated_absorpt_t_max   0.985
_shelx_hkl_checksum              77646
_shelx_res_checksum              25235