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#$Date: 2025-08-20 11:41:31 +0200 (Wed 20 de Aug de 2025) $
#$Revision: 301828 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/60/4036096.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4036096
loop_
_publ_author_name
'Chow, Chi Hao Eugene'
'Phan, Hoa'
'Zhang, Xiaojie'
'Wu, Jishan'
_publ_section_title
;
 Sulfur-Doped (Dibenzo)heptazethrene and (Dibenzo)octazethrene
 Diradicaloids.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b02796
_journal_year                    2019
_chemical_formula_moiety         'C14 H9 S'
_chemical_formula_sum            'C14 H9 S'
_chemical_formula_weight         209.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 94.014(19)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.148(6)
_cell_length_b                   8.347(4)
_cell_length_c                   14.363(11)
_cell_measurement_reflns_used    540
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.498
_cell_measurement_theta_min      5.442
_cell_volume                     974.5(11)
_computing_cell_refinement
'SHELXTL, Acta Cryst., Sect. A 2008, 64, 112-122.'
_computing_data_collection       'APEX3 v2016.9.0'
_computing_data_reduction        'Saint, APEX v2014.11.0.'
_computing_molecular_graphics    Ortep3
_computing_publication_material  'APEX3 v2016.9.0'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT, Acta Cryst., Sect. A 2015, A71, 3-8.'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker AXS D8 Venture '
_diffrn_measurement_method       'profile data from θ/2θ scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8859
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.498
_diffrn_reflns_theta_min         5.442
_exptl_absorpt_coefficient_mu    2.559
_exptl_absorpt_correction_T_max  0.874
_exptl_absorpt_correction_T_min  0.464
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_description       rod
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.355
_exptl_crystal_size_mid          0.056
_exptl_crystal_size_min          0.054
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1954
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0373
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0279P)²+0.8263P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0793
_refine_ls_wR_factor_ref         0.0835
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1684
_reflns_number_total             1954
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo9b02796_si_002.cif
_cod_data_source_block           h208
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4036096
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.464
_shelx_estimated_absorpt_t_max   0.874
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
S1 S 0.17860(5) 0.65930(6) 0.40879(3) 0.02021(14) Uani 1 1 d . .
C1 C 0.3576(2) 0.5654(2) 0.45861(11) 0.0172(4) Uani 1 1 d . .
C2 C 0.4152(2) 0.4226(2) 0.42146(11) 0.0161(4) Uani 1 1 d . .
C3 C 0.3350(2) 0.3466(2) 0.33619(11) 0.0169(4) Uani 1 1 d . .
C4 C 0.3503(2) 0.1852(2) 0.31591(12) 0.0204(4) Uani 1 1 d . .
C5 C 0.3093(2) 0.1314(3) 0.22338(13) 0.0239(4) Uani 1 1 d . .
H5 H 0.3224 0.0211 0.2093 0.029 Uiso 1 1 calc R U
C6 C 0.2521(2) 0.2320(3) 0.15438(13) 0.0248(4) Uani 1 1 d . .
H6 H 0.2374 0.1942 0.0920 0.030 Uiso 1 1 calc R U
C7 C 0.2144(2) 0.3927(3) 0.17500(12) 0.0216(4) Uani 1 1 d . .
C8 C 0.1360(2) 0.4974(3) 0.10759(12) 0.0254(5) Uani 1 1 d . .
H8 H 0.1158 0.4617 0.0450 0.030 Uiso 1 1 calc R U
C9 C 0.0895(2) 0.6472(3) 0.13103(12) 0.0266(5) Uani 1 1 d . .
H9 H 0.0403 0.7163 0.0845 0.032 Uiso 1 1 calc R U
C10 C 0.1137(2) 0.7013(3) 0.22389(12) 0.0226(4) Uani 1 1 d . .
H10 H 0.0784 0.8054 0.2402 0.027 Uiso 1 1 calc R U
C11 C 0.1890(2) 0.6024(2) 0.29109(11) 0.0188(4) Uani 1 1 d . .
C12 C 0.2495(2) 0.4490(2) 0.26829(11) 0.0178(4) Uani 1 1 d . .
C13 C 0.4384(2) 0.6386(2) 0.53597(11) 0.0168(4) Uani 1 1 d . .
H13 H 0.3927 0.7330 0.5606 0.020 Uiso 1 1 calc R U
C14 C 0.4008(2) 0.0589(3) 0.38725(13) 0.0263(4) Uani 1 1 d . .
H14A H 0.5168 0.0315 0.3824 0.039 Uiso 1 1 calc R U
H14B H 0.3329 -0.0369 0.3758 0.039 Uiso 1 1 calc R U
H14C H 0.3854 0.1001 0.4499 0.039 Uiso 1 1 calc R U
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
S S 0.3331 0.5567 '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_site_symmetry_1
_geom_angle_site_symmetry_3
C1 S1 C11 100.10(9) . .
C13 C1 C2 121.70(16) . .
C13 C1 S1 117.40(15) . .
C2 C1 S1 120.90(13) . .
C13 C2 C1 116.28(16) 3_666 .
C13 C2 C3 121.02(17) 3_666 .
C1 C2 C3 122.48(16) . .
C4 C3 C12 118.76(16) . .
C4 C3 C2 123.14(16) . .
C12 C3 C2 117.88(17) . .
C3 C4 C5 119.02(17) . .
C3 C4 C14 124.13(17) . .
C5 C4 C14 116.78(18) . .
C6 C5 C4 122.3(2) . .
C6 C5 H5 118.8 . .
C4 C5 H5 118.8 . .
C5 C6 C7 120.23(17) . .
C5 C6 H6 119.9 . .
C7 C6 H6 119.9 . .
C6 C7 C8 122.34(17) . .
C6 C7 C12 118.45(17) . .
C8 C7 C12 119.14(19) . .
C9 C8 C7 121.18(17) . .
C9 C8 H8 119.4 . .
C7 C8 H8 119.4 . .
C8 C9 C10 120.51(18) . .
C8 C9 H9 119.7 . .
C10 C9 H9 119.7 . .
C11 C10 C9 119.7(2) . .
C11 C10 H10 120.1 . .
C9 C10 H10 120.1 . .
C10 C11 C12 121.54(17) . .
C10 C11 S1 117.38(15) . .
C12 C11 S1 120.35(13) . .
C11 C12 C7 117.58(16) . .
C11 C12 C3 122.62(16) . .
C7 C12 C3 119.70(18) . .
C1 C13 C2 121.97(17) . 3_666
C1 C13 H13 119.0 . .
C2 C13 H13 119.0 3_666 .
C4 C14 H14A 109.5 . .
C4 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
C4 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C1 1.763(2) .
S1 C11 1.764(2) .
C1 C13 1.392(2) .
C1 C2 1.400(3) .
C2 C13 1.399(2) 3_666
C2 C3 1.489(2) .
C3 C4 1.386(3) .
C3 C12 1.440(2) .
C4 C5 1.420(3) .
C4 C14 1.507(3) .
C5 C6 1.356(3) .
C5 H5 0.9500 .
C6 C7 1.412(3) .
C6 H6 0.9500 .
C7 C8 1.422(3) .
C7 C12 1.430(3) .
C8 C9 1.356(3) .
C8 H8 0.9500 .
C9 C10 1.409(3) .
C9 H9 0.9500 .
C10 C11 1.381(3) .
C10 H10 0.9500 .
C11 C12 1.418(3) .
C13 C2 1.399(2) 3_666
C13 H13 0.9500 .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
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_site_symmetry_1
_geom_torsion_site_symmetry_4
C11 S1 C1 C13 149.18(14) . .
C11 S1 C1 C2 -30.93(16) . .
C13 C1 C2 C13 -2.5(3) . 3_666
S1 C1 C2 C13 177.65(13) . 3_666
C13 C1 C2 C3 -177.09(16) . .
S1 C1 C2 C3 3.0(2) . .
C13 C2 C3 C4 28.4(3) 3_666 .
C1 C2 C3 C4 -157.27(17) . .
C13 C2 C3 C12 -146.26(17) 3_666 .
C1 C2 C3 C12 28.1(2) . .
C12 C3 C4 C5 11.6(2) . .
C2 C3 C4 C5 -162.94(16) . .
C12 C3 C4 C14 -165.34(16) . .
C2 C3 C4 C14 20.1(3) . .
C3 C4 C5 C6 -1.5(3) . .
C14 C4 C5 C6 175.72(17) . .
C4 C5 C6 C7 -6.9(3) . .
C5 C6 C7 C8 -172.31(17) . .
C5 C6 C7 C12 4.6(3) . .
C6 C7 C8 C9 174.79(18) . .
C12 C7 C8 C9 -2.1(3) . .
C7 C8 C9 C10 -1.9(3) . .
C8 C9 C10 C11 1.6(3) . .
C9 C10 C11 C12 2.7(3) . .
C9 C10 C11 S1 -167.48(14) . .
C1 S1 C11 C10 -153.65(15) . .
C1 S1 C11 C12 36.01(16) . .
C10 C11 C12 C7 -6.5(3) . .
S1 C11 C12 C7 163.41(13) . .
C10 C11 C12 C3 177.09(16) . .
S1 C11 C12 C3 -13.0(2) . .
C6 C7 C12 C11 -170.88(16) . .
C8 C7 C12 C11 6.1(2) . .
C6 C7 C12 C3 5.6(2) . .
C8 C7 C12 C3 -177.39(16) . .
C4 C3 C12 C11 162.58(17) . .
C2 C3 C12 C11 -22.6(2) . .
C4 C3 C12 C7 -13.7(2) . .
C2 C3 C12 C7 161.12(15) . .
C2 C1 C13 C2 2.6(3) . 3_666
S1 C1 C13 C2 -177.51(14) . 3_666
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168329741
