#------------------------------------------------------------------------------
#$Date: 2025-08-19 21:00:13 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301809 $
#$URL: svn://www.crystallography.net/cod/cif/2/31/12/2311226.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2311226
loop_
_publ_author_name
'Mague, Joel T.'
'Mohamed, Shaaban K.'
'Akkurt, Mehmet'
'Hassan, Alaa A.'
'Albayati, Mustafa R.'
_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       'SAINT (Bruker, 2013)'
_computing_data_collection       'APEX2 (Bruker, 2013)'
_computing_data_reduction        'SAINT (Bruker, 2013)'
_computing_molecular_graphics
'DIAMOND (Brandenburg & Putz, 2012) and ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008b)'
_computing_structure_refinement  'SHELXL2014 (Sheldrick, 2008b)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008b)'
_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       'φ and ω 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   '(TWINABS; 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/[σ²(Fo²)+(0.0674P)²+1.7625P] where P=(Fo²+2Fc²)/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>2σ(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
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,y,1/2-z
3 -x,-y,-z
4 x,-y,1/2+z
5 1/2+x,1/2+y,z
6 1/2-x,1/2+y,1/2-z
7 1/2-x,1/2-y,-z
8 1/2+x,1/2-y,1/2+z
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
S S1 0.33502(7) 0.94435(6) 1.03564(4) 0.0358(2) Uani d U 1.000
N N1 0.42067(18) 0.80829(17) 0.93431(12) 0.0221(6) Uani d U 1.000
N N2 0.5566(2) 0.7153(2) 1.02559(14) 0.0355(8) Uani d U 1.000
N N3 0.5050(2) 0.7828(2) 1.06315(14) 0.0364(8) Uani d U 1.000
C C1 0.4168(2) 0.8470(2) 1.00689(15) 0.0259(8) Uani d U 1.000
C C2 0.5122(2) 0.7230(2) 0.93878(15) 0.0252(7) Uani d U 1.000
C C3 0.4680(2) 0.6091(2) 0.90472(18) 0.0321(9) Uani d U 1.000
C C4 0.5715(3) 0.5557(3) 0.8784(3) 0.0627(14) Uani d U 1.000
C C5 0.6575(4) 0.6450(3) 0.8686(3) 0.0695(16) Uani d U 1.000
C C6 0.6150(2) 0.7526(2) 0.89633(17) 0.0321(9) Uani d U 1.000
C C7 0.3486(2) 0.8458(2) 0.86065(14) 0.0214(7) Uani d U 1.000
C C8 0.2459(2) 0.7876(2) 0.82843(16) 0.0289(8) Uani d U 1.000
C C9 0.1807(3) 0.8195(3) 0.75431(17) 0.0374(9) Uani d U 1.000
C C10 0.2175(3) 0.9075(3) 0.71427(16) 0.0389(10) Uani d U 1.000
C C11 0.3174(3) 0.9671(2) 0.74808(16) 0.0358(9) Uani d U 1.000
C C12 0.3844(2) 0.9370(2) 0.82186(16) 0.0280(8) Uani d U 1.000
H H3A 0.44130 0.56350 0.94620 0.0380 Uiso c RU 1.000
H H3B 0.40080 0.61790 0.85890 0.0380 Uiso c RU 1.000
H H4A 0.60970 0.50130 0.91890 0.0750 Uiso c RU 1.000
H H4B 0.54480 0.51630 0.82710 0.0750 Uiso c RU 1.000
H H5A 0.66400 0.65090 0.81160 0.0840 Uiso c RU 1.000
H H5B 0.73710 0.62700 0.90030 0.0840 Uiso c RU 1.000
H H6A 0.58690 0.80240 0.85030 0.0380 Uiso c RU 1.000
H H6B 0.67980 0.79020 0.93380 0.0380 Uiso c RU 1.000
H H8 0.22050 0.72710 0.85660 0.0350 Uiso c RU 1.000
H H9 0.11060 0.78020 0.73130 0.0450 Uiso c RU 1.000
H H10 0.17400 0.92750 0.66290 0.0470 Uiso c RU 1.000
H H11 0.34040 1.02950 0.72060 0.0430 Uiso c RU 1.000
H H12 0.45330 0.97790 0.84520 0.0340 Uiso c RU 1.000
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C1 N1 C2 110.7(2) no
C1 N1 C7 125.8(2) no
C2 N1 C7 123.6(2) no
N3 N2 C2 111.6(2) no
N2 N3 C1 110.0(2) no
S1 C1 N1 130.9(2) no
S1 C1 N3 122.94(19) no
N1 C1 N3 106.1(2) no
N1 C2 N2 101.58(19) no
N1 C2 C3 115.3(2) no
N1 C2 C6 114.9(2) no
N2 C2 C3 110.3(2) no
N2 C2 C6 109.9(2) no
C3 C2 C6 104.8(2) no
C2 C3 C4 105.9(2) no
C3 C4 C5 107.8(3) no
C4 C5 C6 109.0(3) no
C2 C6 C5 106.0(2) no
N1 C7 C8 119.1(2) no
N1 C7 C12 119.6(2) no
C8 C7 C12 121.3(2) no
C7 C8 C9 118.9(2) no
C8 C9 C10 120.2(3) no
C9 C10 C11 120.4(3) no
C10 C11 C12 120.7(2) no
C7 C12 C11 118.4(2) no
C2 C3 H3A 111.00 no
C2 C3 H3B 111.00 no
C4 C3 H3A 111.00 no
C4 C3 H3B 111.00 no
H3A C3 H3B 109.00 no
C3 C4 H4A 110.00 no
C3 C4 H4B 110.00 no
C5 C4 H4A 110.00 no
C5 C4 H4B 110.00 no
H4A C4 H4B 108.00 no
C4 C5 H5A 110.00 no
C4 C5 H5B 110.00 no
C6 C5 H5A 110.00 no
C6 C5 H5B 110.00 no
H5A C5 H5B 108.00 no
C2 C6 H6A 111.00 no
C2 C6 H6B 111.00 no
C5 C6 H6A 111.00 no
C5 C6 H6B 111.00 no
H6A C6 H6B 109.00 no
C7 C8 H8 121.00 no
C9 C8 H8 121.00 no
C8 C9 H9 120.00 no
C10 C9 H9 120.00 no
C9 C10 H10 120.00 no
C11 C10 H10 120.00 no
C10 C11 H11 120.00 no
C12 C11 H11 120.00 no
C7 C12 H12 121.00 no
C11 C12 H12 121.00 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C1 1.636(3) no
N1 C1 1.331(3) no
N1 C2 1.461(3) no
N1 C7 1.434(3) no
N2 N3 1.253(3) no
N2 C2 1.470(3) no
N3 C1 1.470(3) no
C2 C3 1.537(3) no
C2 C6 1.542(3) no
C3 C4 1.495(4) no
C4 C5 1.491(6) no
C5 C6 1.494(5) no
C7 C8 1.389(3) no
C7 C12 1.385(3) no
C8 C9 1.390(4) no
C9 C10 1.371(5) no
C10 C11 1.380(5) no
C11 C12 1.387(4) no
C3 H3A 0.9900 no
C3 H3B 0.9900 no
C4 H4A 0.9900 no
C4 H4B 0.9900 no
C5 H5A 0.9900 no
C5 H5B 0.9900 no
C6 H6A 0.9900 no
C6 H6B 0.9900 no
C8 H8 0.9500 no
C9 H9 0.9500 no
C10 H10 0.9500 no
C11 H11 0.9500 no
C12 H12 0.9500 no
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_publ_flag
C2 N1 C1 S1 177.9(2) no
C2 N1 C1 N3 -2.4(3) no
C7 N1 C1 S1 -0.4(4) no
C7 N1 C1 N3 179.3(2) no
C1 N1 C2 N2 2.4(3) no
C1 N1 C2 C3 121.7(2) no
C1 N1 C2 C6 -116.2(2) no
C7 N1 C2 N2 -179.3(2) no
C7 N1 C2 C3 -60.0(3) no
C7 N1 C2 C6 62.1(3) no
C1 N1 C7 C8 -96.5(3) no
C1 N1 C7 C12 85.5(3) no
C2 N1 C7 C8 85.5(3) no
C2 N1 C7 C12 -92.6(3) no
C2 N2 N3 C1 0.1(3) no
N3 N2 C2 N1 -1.5(3) no
N3 N2 C2 C3 -124.2(2) no
N3 N2 C2 C6 120.7(2) no
N2 N3 C1 S1 -178.8(2) no
N2 N3 C1 N1 1.5(3) no
N1 C2 C3 C4 153.1(3) no
N2 C2 C3 C4 -92.6(3) no
C6 C2 C3 C4 25.7(3) no
N1 C2 C6 C5 -149.9(3) no
N2 C2 C6 C5 96.3(3) no
C3 C2 C6 C5 -22.2(3) no
C2 C3 C4 C5 -19.6(4) no
C3 C4 C5 C6 5.6(5) no
C4 C5 C6 C2 10.6(4) no
N1 C7 C8 C9 -175.6(2) no
C12 C7 C8 C9 2.5(4) no
N1 C7 C12 C11 175.7(2) no
C8 C7 C12 C11 -2.3(4) no
C7 C8 C9 C10 -0.4(4) no
C8 C9 C10 C11 -1.9(5) no
C9 C10 C11 C12 2.1(5) no
C10 C11 C12 C7 0.0(4) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 13680317
