Synthesis and Structural Characterization of 1-Arylimidazole-2-thiones and N,N'-Aryldiethoxyethylthioureas with Electronically Diverse Substituents: A Manifold of Hydrogen Bonding Networks.
Palmer, Joshua H.; Parkin, Gerard; New journal of chemistry = Nouveau journal de chimie 38 (2014) 4071–4082; doi:10.1039/C4NJ00521J

data_7054264
_publ_section_title
;
 Synthesis and Structural Characterization of 1-Arylimidazole-2-thiones
 and N,N'-Aryldiethoxyethylthioureas with Electronically Diverse
 Substituents: A Manifold of Hydrogen Bonding Networks.
;
_journal_issue                   9
_journal_name_full
'New journal of chemistry = Nouveau journal de chimie'
_journal_page_first              4071
_journal_page_last               4082
_journal_paper_doi               10.1039/C4NJ00521J
_journal_volume                  38
_journal_year                    2014
_chemical_formula_sum            'C11 H6 F6 N2 S'
_chemical_formula_weight         312.24
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            24
_cell_length_a                   8.4302(5)
_cell_length_b                   23.8152(15)
_cell_length_c                   36.666(2)
_cell_measurement_reflns_used    9181
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      32.63
_cell_measurement_theta_min      2.38
_cell_volume                     7361.3(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      130(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_unetI/netI     0.0180
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       52
_diffrn_reflns_limit_l_min       -52
_diffrn_reflns_number            117976
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.508
_diffrn_reflns_theta_min         1.402
_exptl_absorpt_coefficient_mu    0.329
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_correction_T_min  0.6329
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.690
_exptl_crystal_description       plate
_exptl_crystal_F_000             3744
_exptl_crystal_size_max          0.660
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.448
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
; 
 Refined as an inversion twin. 
;
_refine_ls_abs_structure_Flack   0.34(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1247
_refine_ls_number_reflns         22429
_refine_ls_number_restraints     670
_refine_ls_restrained_S_all      1.116
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0358
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0420P)^2^+3.1799P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0870
_refine_ls_wR_factor_ref         0.0882
_reflns_Friedel_coverage         0.825
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                21428
_reflns_number_total             22429
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4nj00521j2.cif
_cod_data_source_block           hmimcf30514
_cod_depositor_comments
;Adding full bibliography for 7054264--7054271.cif.

 Adding full bibliography for 7054264--7054403.cif.
;
_cod_original_cell_volume        7361.4(8)
_cod_database_code               7054264
_shelx_estimated_absorpt_t_min   0.812
_shelx_estimated_absorpt_t_max   0.977
_shelxl_version_number           2013-4
_shelx_res_checksum              89023