Crystal structure of N-ethyl-4-[3-(trifluoromethyl)-phenyl]piperazine-1-carbothioamide, C14H18F3N3S
Al-Wahaibi, Lamya H.; Blacque, Olivier; Al-Shaalan, Nora H.; Tiekink, Edward R. T.; El-Emam, Ali A.; Zeitschrift für Kristallographie - New Crystal Structures 238 (2023) 45–47; doi:10.1515/ncrs-2022-0450

data_8107348
_publ_section_title
;
 Crystal structure of
 N-ethyl-4-[3-(trifluoromethyl)-phenyl]piperazine-1-carbothioamide,
 C14H18F3N3S
;
_journal_issue                   1
_journal_name_full
'Zeitschrift f\"ur Kristallographie - New Crystal Structures'
_journal_page_first              45
_journal_page_last               47
_journal_paper_doi               10.1515/ncrs-2022-0450
_journal_volume                  238
_journal_year                    2023
_chemical_formula_moiety         'C14 H18 F3 N3 S'
_chemical_formula_sum            'C14 H18 F3 N3 S'
_chemical_formula_weight         317.37
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-09-01
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 94.4768(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.61919(4)
_cell_length_b                   29.1507(3)
_cell_length_c                   11.27803(10)
_cell_measurement_reflns_used    11444
_cell_measurement_temperature    160(1)
_cell_measurement_theta_max      76.2470
_cell_measurement_theta_min      3.0020
_cell_volume                     1513.98(2)
_computing_cell_refinement       'CrysAlisPro [1]'
_computing_data_collection       'CrysAlisPro [1]'
_computing_data_reduction        'CrysAlisPro [1]'
_computing_molecular_graphics    'OLEX2 [4]'
_computing_publication_material  'OLEX2 [4]'
_computing_structure_refinement  'SHELXL [3]'
_computing_structure_solution    'SHELXT [2]'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      160(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3801
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -65.00  30.20   0.80    3.00    --  -42.61  37.00-120.00  119
  2  \w    -65.00  30.20   0.80    3.00    --  -42.61  37.00   0.00  119
  3  \w    -87.00  -5.40   0.80    3.00    --  -42.61 125.00 -60.00  102
  4  \w     36.00 108.00   0.80   12.00    --  111.00-111.00  90.00   90
  5  \w    104.00 178.40   0.80   12.00    --  111.00 111.00-120.00   93
  6  \w     36.00 135.20   0.80   12.00    --  111.00 -30.00 150.00  124
  7  \w     87.00 178.20   0.80   12.00    --  111.00  45.00   0.00  114
  8  \w     87.00 178.20   0.80   12.00    --  111.00  45.00  60.00  114
  9  \w    104.00 178.40   0.80   12.00    --  111.00 111.00   0.00   93
 10  \w    104.00 178.40   0.80   12.00    --  111.00 111.00 -90.00   93
 11  \w    104.00 178.40   0.80   12.00    --  111.00 111.00 150.00   93
 12  \w     36.00 108.00   0.80   12.00    --  111.00-111.00-120.00   90
 13  \w     30.00 106.80   0.80   12.00    --  111.00 -94.00 150.00   96
 14  \w     83.00 178.20   0.80   12.00    --  111.00  61.00-120.00  119
 15  \w   -113.00 -15.40   0.80    3.00    --  -42.61 -57.00  60.00  122
 16  \w   -113.00 -15.40   0.80    3.00    --  -42.61 -57.00-150.00  122
 17  \w   -113.00 -15.40   0.80    3.00    --  -42.61 -57.00 -60.00  122
 18  \w     83.00 114.20   0.80   12.00    --  111.00  61.00 -60.00   39
 19  \w     87.00 178.20   0.80   12.00    --  111.00  45.00-180.00  114
 20  \w     83.00 178.20   0.80   12.00    --  111.00  61.00 120.00  119
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.2454388000
_diffrn_orient_matrix_UB_12      0.0348152000
_diffrn_orient_matrix_UB_13      0.0306342000
_diffrn_orient_matrix_UB_21      -0.0383075000
_diffrn_orient_matrix_UB_22      0.0191168000
_diffrn_orient_matrix_UB_23      -0.1276441000
_diffrn_orient_matrix_UB_31      -0.2239798000
_diffrn_orient_matrix_UB_32      0.0348669000
_diffrn_orient_matrix_UB_33      0.0393390000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0162
_diffrn_reflns_av_unetI/netI     0.0097
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15788
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.504
_diffrn_reflns_theta_min         3.032
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.181
_exptl_absorpt_correction_T_max  0.934
_exptl_absorpt_correction_T_min  0.722
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro [1]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_description       plate
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_refine_diff_density_max         1.038
_refine_diff_density_min         -0.653
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         3093
_refine_ls_number_restraints     144
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0588
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0812P)^2^+2.1020P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1564
_refine_ls_wR_factor_ref         0.1579
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2960
_reflns_number_total             3093
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            suppl_j_ncrs-2022-0450_suppl.cif
_cod_data_source_block           shelx
_cod_original_cell_volume        1513.99(3)
_cod_database_code               8107348
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.937
_shelx_estimated_absorpt_t_min   0.682
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 F1B-C14 \\sim F1A-C14 \\sim F2B-C14 \\sim F2A-C14 \\sim F3B-C14 \\sim F3A-C14
 with sigma of 0.005
 F3B-F1B \\sim F2B-F3B \\sim F2B-F1B
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C14 \\sim F1A \\sim F1B \\sim F2A \\sim F2B \\sim F3A \\sim F3B: within 3A with
sigma of 0.001 and sigma for terminal atoms of 0.002 within 3A
4. Others
 Sof(F1B)=Sof(F2B)=Sof(F3B)=1-FVAR(1)
 Sof(F1A)=Sof(F2A)=Sof(F3A)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B)
5.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C11(H11), C12(H12), C13(H13)
5.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_shelx_res_checksum              69020
_shelx_hkl_checksum              90064