4-Phenyl-1,2,4-tri-aza-spiro-[4.4]non-1-ene-3-thione.
Mague, Joel T.; Mohamed, Shaaban K.; Akkurt, Mehmet; Hassan, Alaa A.; Albayati, Mustafa R.; Acta crystallographica. Section E, Structure reports online 70 (2014) o433–4; doi:10.1107/S1600536814005418

data_2311226
_publ_section_title
;
 4-Phenyl-1,2,4-tri-aza-spiro-[4.4]non-1-ene-3-thione.
;
_journal_coeditor_code           RZ5108
_journal_issue                   'Pt 4'
_journal_name_full
'Acta crystallographica. Section E, Structure reports online'
_journal_page_first              o433
_journal_page_last               4
_journal_paper_doi               10.1107/S1600536814005418
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C12 H13 N3 S'
_chemical_formula_moiety         'C12 H13 N3 S'
_chemical_formula_sum            'C12 H13 N3 S'
_chemical_formula_weight         231.32
_chemical_name_systematic
;
4-Phenyl-1,2,4-triazaspiro[4.4]non-1-ene-3-thione
;
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 101.3060(14)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.4780(12)
_cell_length_b                   12.0452(12)
_cell_length_c                   17.0439(17)
_cell_measurement_reflns_used    8834
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      29.1130
_cell_measurement_theta_min      2.4372
_cell_volume                     2310.7(4)
_computing_cell_refinement       '<i>SAINT</i> (Bruker, 2013)'
_computing_data_collection       '<i>APEX2</i> (Bruker, 2013)'
_computing_data_reduction        '<i>SAINT</i> (Bruker, 2013)'
_computing_molecular_graphics
'DIAMOND (Brandenburg & Putz, 2012) and ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  '<i>SHELXTL</i> (Sheldrick, 2008<i>b</i>)'
_computing_structure_refinement  '<i>SHELXL2014</i> (Sheldrick, 2008<i>b</i>)'
_computing_structure_solution    '<i>SHELXTL</i> (Sheldrick, 2008<i>b</i>)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 8.3660
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0497
_diffrn_reflns_av_sigmaI/netI    0.0688
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            29725
_diffrn_reflns_reduction_process
;
;
_diffrn_reflns_theta_full        28.75
_diffrn_reflns_theta_max         29.19
_diffrn_reflns_theta_min         2.44
_exptl_absorpt_coefficient_mu    0.255
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.96
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(<i>TWINABS</i>; Sheldrick, 2009)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.615
_refine_diff_density_min         -0.645
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         29725
_refine_ls_number_restraints     44
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0807
_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^)+(0.0674P)^2^+1.7625P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1489
_refine_ls_wR_factor_ref         0.1680
_reflns_number_gt                21519
_reflns_number_total             29725
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            rz5108sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2311226