#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:52:15 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301804 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/46/2214692.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_2214692
loop_
_publ_author_name
'Nengfang She'
'Wei Huang'
_publ_section_title
;
 (4-Oxo-3,4-dihydroquinazolin-3-yl)methyl piperidine-1-carbodithioate
;
_journal_coeditor_code           HB2479
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3617
_journal_page_last               o3617
_journal_paper_doi               10.1107/S1600536807036203
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C15 H17 N3 O S2'
_chemical_formula_moiety         'C15 H17 N3 O S2'
_chemical_formula_sum            'C15 H17 N3 O S2'
_chemical_formula_weight         319.44
_chemical_name_systematic
;
(4-Oxo-3,4-dihydroquinazolin-3-yl)methyl piperidine-1-carbodithioate
;
_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           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 108.354(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.0217(12)
_cell_length_b                   8.4199(9)
_cell_length_c                   17.2294(19)
_cell_measurement_reflns_used    2499
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      24.39
_cell_measurement_theta_min      2.49
_cell_volume                     1517.6(3)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXTL (Bruker, 2001)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      292(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART 4K CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_sigmaI/netI    0.0315
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            8066
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         1.95
_exptl_absorpt_coefficient_mu    0.353
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.193
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2982
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0483
_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/[σ²(Fo²)+(0.0622P)²+0.3628P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1184
_refine_ls_wR_factor_ref         0.1249
_reflns_number_gt                2425
_reflns_number_total             2982
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb2479.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2214692
_cod_database_fobs_code          2214692
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
C C1 0.5285(2) 1.0998(2) 0.10061(13) 0.0421(5) Uani d . 1
C C2 0.4044(2) 1.0422(3) 0.08460(15) 0.0544(6) Uani d . 1
H H2 0.3890 0.9570 0.1145 0.065 Uiso calc R 1
C C3 0.3050(3) 1.1106(3) 0.02491(17) 0.0647(7) Uani d . 1
H H3 0.2222 1.0726 0.0146 0.078 Uiso calc R 1
C C4 0.3285(3) 1.2365(3) -0.01997(16) 0.0647(7) Uani d . 1
H H4 0.2609 1.2825 -0.0605 0.078 Uiso calc R 1
C C5 0.4488(3) 1.2942(3) -0.00588(15) 0.0570(6) Uani d . 1
H H5 0.4629 1.3781 -0.0371 0.068 Uiso calc R 1
C C6 0.5516(2) 1.2276(2) 0.05554(13) 0.0458(5) Uani d . 1
C C7 0.7630(2) 1.2294(3) 0.12735(14) 0.0496(5) Uani d . 1
H H7 0.8442 1.2730 0.1380 0.060 Uiso calc R 1
C C8 0.6342(2) 1.0307(2) 0.16534(13) 0.0432(5) Uani d . 1
C C9 0.8636(2) 1.0460(3) 0.23950(13) 0.0505(6) Uani d . 1
H H9A 0.8447 1.0497 0.2908 0.061 Uiso calc R 1
H H9B 0.9342 1.1181 0.2440 0.061 Uiso calc R 1
C C10 1.0075(2) 0.8722(3) 0.15837(13) 0.0457(5) Uani d . 1
C C11 1.0068(3) 0.5750(3) 0.15399(18) 0.0640(7) Uani d . 1
H H11A 0.9557 0.5205 0.1050 0.077 Uiso calc R 1
H H11B 0.9562 0.5846 0.1907 0.077 Uiso calc R 1
C C12 1.1246(3) 0.4807(3) 0.19436(17) 0.0659(7) Uani d . 1
H H12A 1.1005 0.3750 0.2065 0.079 Uiso calc R 1
H H12B 1.1718 0.5309 0.2457 0.079 Uiso calc R 1
C C13 1.2096(3) 0.4680(3) 0.14057(19) 0.0718(8) Uani d . 1
H H13A 1.1665 0.4067 0.0920 0.086 Uiso calc R 1
H H13B 1.2881 0.4135 0.1699 0.086 Uiso calc R 1
C C14 1.2404(3) 0.6332(4) 0.11589(19) 0.0744(8) Uani d . 1
H H14A 1.2932 0.6893 0.1638 0.089 Uiso calc R 1
H H14B 1.2881 0.6240 0.0775 0.089 Uiso calc R 1
C C15 1.1202(3) 0.7259(3) 0.07737(17) 0.0717(8) Uani d . 1
H H15A 1.1420 0.8325 0.0650 0.086 Uiso calc R 1
H H15B 1.0715 0.6757 0.0264 0.086 Uiso calc R 1
N N1 0.75210(17) 1.1016(2) 0.17428(10) 0.0416(4) Uani d . 1
N N2 0.6728(2) 1.2941(2) 0.07065(12) 0.0533(5) Uani d . 1
N N3 1.0413(2) 0.7346(2) 0.13230(13) 0.0605(6) Uani d . 1
O O1 0.62564(16) 0.92246(19) 0.21039(10) 0.0564(4) Uani d . 1
S S1 0.91313(6) 0.84706(7) 0.22454(4) 0.0515(2) Uani d . 1
S S2 1.04652(7) 1.04974(7) 0.13190(4) 0.0617(2) Uani d . 1
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'
O O 0.0106 0.0060 '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
C2 C1 C6 119.8(2)
C2 C1 C8 120.7(2)
C6 C1 C8 119.5(2)
C3 C2 C1 120.3(2)
C3 C2 H2 119.8
C1 C2 H2 119.8
C2 C3 C4 119.6(2)
C2 C3 H3 120.2
C4 C3 H3 120.2
C5 C4 C3 121.2(2)
C5 C4 H4 119.4
C3 C4 H4 119.4
C4 C5 C6 120.2(2)
C4 C5 H5 119.9
C6 C5 H5 119.9
N2 C6 C1 122.5(2)
N2 C6 C5 118.6(2)
C1 C6 C5 118.9(2)
N2 C7 N1 126.4(2)
N2 C7 H7 116.8
N1 C7 H7 116.8
O1 C8 N1 120.4(2)
O1 C8 C1 125.6(2)
N1 C8 C1 113.98(18)
N1 C9 S1 114.06(15)
N1 C9 H9A 108.7
S1 C9 H9A 108.7
N1 C9 H9B 108.7
S1 C9 H9B 108.7
H9A C9 H9B 107.6
N3 C10 S2 124.41(17)
N3 C10 S1 113.08(16)
S2 C10 S1 122.50(14)
N3 C11 C12 110.3(2)
N3 C11 H11A 109.6
C12 C11 H11A 109.6
N3 C11 H11B 109.6
C12 C11 H11B 109.6
H11A C11 H11B 108.1
C11 C12 C13 111.5(2)
C11 C12 H12A 109.3
C13 C12 H12A 109.3
C11 C12 H12B 109.3
C13 C12 H12B 109.3
H12A C12 H12B 108.0
C12 C13 C14 110.0(2)
C12 C13 H13A 109.7
C14 C13 H13A 109.7
C12 C13 H13B 109.7
C14 C13 H13B 109.7
H13A C13 H13B 108.2
C15 C14 C13 110.8(3)
C15 C14 H14A 109.5
C13 C14 H14A 109.5
C15 C14 H14B 109.5
C13 C14 H14B 109.5
H14A C14 H14B 108.1
N3 C15 C14 111.0(2)
N3 C15 H15A 109.4
C14 C15 H15A 109.4
N3 C15 H15B 109.4
C14 C15 H15B 109.4
H15A C15 H15B 108.0
C7 N1 C8 121.46(19)
C7 N1 C9 119.77(19)
C8 N1 C9 118.58(18)
C7 N2 C6 116.2(2)
C10 N3 C15 122.7(2)
C10 N3 C11 125.7(2)
C15 N3 C11 111.6(2)
C10 S1 C9 104.16(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.394(3)
C1 C6 1.396(3)
C1 C8 1.457(3)
C2 C3 1.371(4)
C2 H2 0.9300
C3 C4 1.384(4)
C3 H3 0.9300
C4 C5 1.361(4)
C4 H4 0.9300
C5 C6 1.401(3)
C5 H5 0.9300
C6 N2 1.396(3)
C7 N2 1.276(3)
C7 N1 1.374(3)
C7 H7 0.9300
C8 O1 1.220(2)
C8 N1 1.394(3)
C9 N1 1.457(3)
C9 S1 1.805(2)
C9 H9A 0.9700
C9 H9B 0.9700
C10 N3 1.337(3)
C10 S2 1.658(2)
C10 S1 1.782(2)
C11 N3 1.477(3)
C11 C12 1.493(4)
C11 H11A 0.9700
C11 H11B 0.9700
C12 C13 1.514(4)
C12 H12A 0.9700
C12 H12B 0.9700
C13 C14 1.524(4)
C13 H13A 0.9700
C13 H13B 0.9700
C14 C15 1.500(4)
C14 H14A 0.9700
C14 H14B 0.9700
C15 N3 1.475(3)
C15 H15A 0.9700
C15 H15B 0.9700
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C11 H11B O1 2_645 0.97 2.56 3.375(3) 142
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
C6 C1 C2 C3 -0.1(3)
C8 C1 C2 C3 178.4(2)
C1 C2 C3 C4 0.6(4)
C2 C3 C4 C5 -0.1(4)
C3 C4 C5 C6 -0.8(4)
C2 C1 C6 N2 177.7(2)
C8 C1 C6 N2 -0.8(3)
C2 C1 C6 C5 -0.7(3)
C8 C1 C6 C5 -179.24(19)
C4 C5 C6 N2 -177.3(2)
C4 C5 C6 C1 1.2(3)
C2 C1 C8 O1 -0.8(3)
C6 C1 C8 O1 177.7(2)
C2 C1 C8 N1 -179.60(18)
C6 C1 C8 N1 -1.1(3)
N3 C11 C12 C13 -57.0(3)
C11 C12 C13 C14 54.9(3)
C12 C13 C14 C15 -53.9(3)
C13 C14 C15 N3 55.9(3)
N2 C7 N1 C8 -2.2(3)
N2 C7 N1 C9 -177.1(2)
O1 C8 N1 C7 -176.3(2)
C1 C8 N1 C7 2.5(3)
O1 C8 N1 C9 -1.4(3)
C1 C8 N1 C9 177.51(17)
S1 C9 N1 C7 -116.52(19)
S1 C9 N1 C8 68.4(2)
N1 C7 N2 C6 0.1(3)
C1 C6 N2 C7 1.4(3)
C5 C6 N2 C7 179.8(2)
S2 C10 N3 C15 1.1(4)
S1 C10 N3 C15 -179.6(2)
S2 C10 N3 C11 -179.3(2)
S1 C10 N3 C11 0.0(3)
C14 C15 N3 C10 121.4(3)
C14 C15 N3 C11 -58.3(3)
C12 C11 N3 C10 -121.2(3)
C12 C11 N3 C15 58.4(3)
N3 C10 S1 C9 -172.68(17)
S2 C10 S1 C9 6.57(18)
N1 C9 S1 C10 82.82(18)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21123887
2 PubChem 139072705
