Prevalence of the thioamide {⋯H–N–CS}2 synthon—solid-state (X-ray crystallography), solution (NMR) and gas-phase (theoretical) structures of O-methyl-N-aryl-thiocarbamides
Ho, Soo Yei; Bettens, Ryan P. A.; Dakternieks, Dainis; Duthie, Andrew; Tiekink, Edward R. T.; CrystEngComm 7 (2005) 682–; doi:10.1039/b514254g

data_7216126
_publ_section_title
;
 Prevalence of the thioamide {&#x22EF;H--N--C&#xE001;S}2
 synthon---solid-state (X-ray crystallography), solution (NMR) and
 gas-phase (theoretical) structures of O-methyl-N-aryl-thiocarbamides
;
_journal_issue                   113
_journal_name_full               CrystEngComm
_journal_page_first              682
_journal_paper_doi               10.1039/b514254g
_journal_volume                  7
_journal_year                    2005
_chemical_formula_sum            'C8 H8 N2 O3 S'
_chemical_formula_weight         212.22
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 95.632(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.3340(6)
_cell_length_b                   7.6604(6)
_cell_length_c                   16.1964(11)
_cell_measurement_reflns_used    1614
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      29.9
_cell_measurement_theta_min      2.5
_cell_volume                     905.54(12)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SHELXTL (Bruker, 2000)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'Bruker SHEXLTL (Bruker, 2000)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'PATTY in DIRDIF92 (Beurskens et al., 1992)'
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker AXS SMART CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.031
_diffrn_reflns_av_sigmaI/netI    0.043
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            7354
_diffrn_reflns_theta_full        30.0
_diffrn_reflns_theta_max         30.0
_diffrn_reflns_theta_min         2.5
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.338
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.816
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS, Bruker, 2000 & Blessing, 1995)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.557
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.49
_refine_diff_density_min         -0.23
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.06
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         2631
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.06
_refine_ls_R_factor_all          0.064
_refine_ls_R_factor_gt           0.049
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.058P)^2^+0.3017P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.114
_refine_ls_wR_factor_ref         0.122
_reflns_number_gt                2090
_reflns_number_total             2631
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            b514254g.txt
_cod_data_source_block           (MeO)C(=S)N(H)C6H4NO2-4
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               7216126