Evaluation of N—H···S and N—H···π interactions in <i>O</i>,<i>O</i>'-diethyl <i>N</i>-(2,4,6-trimethylphenyl)thiophosphate: a combination of X-ray crystallographic and theoretical studies
Torabi Farkhani, Elham; Pourayoubi, Mehrdad; Izadyar, Mohammad; Andreev, Pavel V.; Shchegravina, Ekaterina S.; Acta Crystallographica Section C 74 (2018) 847–855; doi:10.1107/S2053229618007933

data_2021194
_publ_section_title
;
 Evaluation of N---H&#x00B7;&#x00B7;&#x00B7;S and
 N---H&#x00B7;&#x00B7;&#x00B7;\p interactions in
 <i>O</i>,<i>O</i>'-diethyl <i>N</i>-(2,4,6-trimethylphenyl)thiophosphate:
 a combination of X-ray crystallographic and theoretical studies
;
_journal_coeditor_code           KY3141
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              847
_journal_page_last               855
_journal_paper_doi               10.1107/S2053229618007933
_journal_volume                  74
_journal_year                    2018
_chemical_formula_iupac          'C13 H22 N O2 P S'
_chemical_formula_moiety         'C13 H22 N O2 P S'
_chemical_formula_sum            'C13 H22 N O2 P S'
_chemical_formula_weight         287.34
_chemical_name_common
;
<i>N</i>-[Diethoxy(sulfanylidene)-\l^5^-phosphanyl]-2,4,6-trimethylaniline
;
_chemical_name_systematic
;
<i>O</i>,<i>O</i>'-Diethyl <i>N</i>-(2,4,6-trimethylphenyl)thiophosphate
;
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                100.366(3)
_cell_angle_beta                 100.314(3)
_cell_angle_gamma                90.093(3)
_cell_formula_units_Z            2
_cell_length_a                   8.4954(3)
_cell_length_b                   8.6790(3)
_cell_length_c                   10.7105(4)
_cell_measurement_reflns_used    7603
_cell_measurement_temperature    100.2(8)
_cell_measurement_theta_max      32.087
_cell_measurement_theta_min      4.224
_cell_volume                     763.79(5)
_computing_cell_refinement
;
CrysAlis PRO (Agilent, 2014)
;
_computing_data_collection
;
CrysAlis PRO (Agilent, 2014)
;
_computing_data_reduction
;
CrysAlis PRO (Agilent, 2014)
;
_computing_molecular_graphics
;
<i>OlexSys</i> (Dolomanov <i>et al</i>., 2009)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100.2(8)
_diffrn_detector_area_resol_mean 8.0151
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Agilent Xcalibur Sapphire3 Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.025
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11026
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         3.401
_exptl_absorpt_coefficient_mu    0.312
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.95144
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis PRO (Agilent, 2014)
;
_exptl_crystal_colour            light-yellow
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_description       bulk
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.2431
_exptl_crystal_size_mid          0.1952
_exptl_crystal_size_min          0.1824
_refine_diff_density_max         0.455
_refine_diff_density_min         -0.234
_refine_ls_abs_structure_details
;
Flack <i>x</i> determined using 2825 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons <i>et al.</i>,  2013)
;
_refine_ls_abs_structure_Flack   -0.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         6232
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0358
_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^)+(0.0551P)^2^+0.0309P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0879
_refine_ls_wR_factor_ref         0.0887
_reflns_number_gt                6048
_reflns_number_total             6232
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ky3141sup1.cif
_cod_data_source_block           I
_cod_database_code               2021194
_cod_database_fobs_code          2021194
_shelx_hkl_checksum              91131
_shelx_res_checksum              82458