#------------------------------------------------------------------------------
#$Date: 2025-08-18 16:30:32 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301775 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/32/1503213.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_1503213
loop_
_publ_author_name
'Linder, Thomas'
'Badiola, Eider'
'Baumgartner, Thomas'
'Sutherland, Todd C.'
_publ_section_title
;
 Synthesis of π-extended thiadiazole (oxides) and their electronic
 properties.
;
_journal_issue                   20
_journal_name_full               'Organic letters'
_journal_page_first              4520
_journal_page_last               4523
_journal_paper_doi               10.1021/ol1018213
_journal_volume                  12
_journal_year                    2010
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C14 H8 N2 O2 S1 '
_chemical_formula_sum            'C14 H8 N2 O2 S'
_chemical_formula_weight         268.294
_chemical_name_common            phenSO2
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2010-03-07T11:56:03-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 112.64(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.9578(4)
_cell_length_b                   17.0550(8)
_cell_length_c                   10.1330(8)
_cell_measurement_reflns_used    2049
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.878
_cell_measurement_theta_min      0.998
_cell_volume                     1109.8(4)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_orient_matrix_type       'by Bruker AXS Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      -0.0581338
_diffrn_orient_matrix_UB_12      -0.0489771
_diffrn_orient_matrix_UB_13      0.0271691
_diffrn_orient_matrix_UB_21      -0.0274289
_diffrn_orient_matrix_UB_22      -0.0204674
_diffrn_orient_matrix_UB_23      -0.0994656
_diffrn_orient_matrix_UB_31      0.1368654
_diffrn_orient_matrix_UB_32      -0.0249049
_diffrn_orient_matrix_UB_33      0.0283133
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_unetI/netI     0.0313
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4250
_diffrn_reflns_theta_full        27.86
_diffrn_reflns_theta_max         27.86
_diffrn_reflns_theta_min         2.48
_exptl_absorpt_coefficient_mu    0.289
_exptl_absorpt_correction_T_max  0.9914
_exptl_absorpt_correction_T_min  0.9525
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'HKL Scalepack'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.606
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.572
_refine_diff_density_min         -0.614
_refine_diff_density_rms         0.158
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.166
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2568
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.166
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0478
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0858P)²+0.9091P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1449
_refine_ls_wR_factor_ref         0.1596
_reflns_number_gt                2310
_reflns_number_total             2568
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            ol1018213_si_002.cif
_cod_data_source_block           PhenSO2
_cod_original_sg_symbol_H-M      P21/c
_cod_original_formula_sum        'C14 H8 N2 O2 S1'
_cod_database_code               1503213
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.3230(3) 0.48774(12) 0.6925(2) 0.0179(4) Uani 1 1 d .
C2 C 0.3436(3) 0.41464(12) 0.6149(2) 0.0179(4) Uani 1 1 d .
C3 C 0.2878(3) 0.41662(12) 0.4616(2) 0.0180(4) Uani 1 1 d .
C4 C 0.3053(3) 0.34871(13) 0.3899(2) 0.0218(4) Uani 1 1 d .
H4 H 0.3517 0.3013 0.4415 0.026 Uiso 1 1 calc R
C5 C 0.2550(4) 0.35054(14) 0.2437(2) 0.0251(5) Uani 1 1 d .
H5 H 0.2704 0.3049 0.1948 0.03 Uiso 1 1 calc R
C6 C 0.1816(4) 0.42023(15) 0.1692(3) 0.0275(5) Uani 1 1 d .
H6 H 0.1443 0.4216 0.0686 0.033 Uiso 1 1 calc R
C7 C 0.1622(3) 0.48757(14) 0.2400(2) 0.0240(5) Uani 1 1 d .
H7 H 0.1109 0.5342 0.1868 0.029 Uiso 1 1 calc R
C8 C 0.2167(3) 0.48819(12) 0.3878(2) 0.0181(4) Uani 1 1 d .
C9 C 0.2016(3) 0.56062(12) 0.4652(2) 0.0181(4) Uani 1 1 d .
C10 C 0.1425(3) 0.63257(13) 0.3942(2) 0.0222(4) Uani 1 1 d .
H10 H 0.1073 0.6349 0.2939 0.027 Uiso 1 1 calc R
C11 C 0.1346(4) 0.70040(13) 0.4673(3) 0.0254(5) Uani 1 1 d .
H11 H 0.0951 0.7485 0.4167 0.03 Uiso 1 1 calc R
C12 C 0.1836(4) 0.69888(13) 0.6138(3) 0.0239(5) Uani 1 1 d .
H12 H 0.1773 0.7456 0.663 0.029 Uiso 1 1 calc R
C13 C 0.2417(3) 0.62896(13) 0.6877(2) 0.0207(4) Uani 1 1 d .
H13 H 0.2743 0.6273 0.7877 0.025 Uiso 1 1 calc R
C14 C 0.2521(3) 0.56050(12) 0.6141(2) 0.0168(4) Uani 1 1 d .
N1 N 0.3755(3) 0.47885(10) 0.8281(2) 0.0215(4) Uani 1 1 d .
N2 N 0.4135(3) 0.35429(11) 0.6969(2) 0.0220(4) Uani 1 1 d .
O1 O 0.3185(3) 0.34452(11) 0.9156(2) 0.0374(5) Uani 1 1 d .
O2 O 0.6728(3) 0.38134(11) 0.9472(2) 0.0380(5) Uani 1 1 d .
S1 S 0.45616(9) 0.38519(3) 0.86439(6) 0.0242(2) Uani 1 1 d .
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 0 '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 0.006 '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
N1 C1 C14 125.54(19)
N1 C1 C2 114.44(18)
C14 C1 C2 120.02(18)
N2 C2 C3 125.84(19)
N2 C2 C1 114.22(18)
C3 C2 C1 119.94(18)
C4 C3 C8 121.52(19)
C4 C3 C2 119.79(19)
C8 C3 C2 118.69(18)
C5 C4 C3 120.0(2)
C5 C4 H4 120
C3 C4 H4 120
C4 C5 C6 119.1(2)
C4 C5 H5 120.4
C6 C5 H5 120.4
C7 C6 C5 120.9(2)
C7 C6 H6 119.6
C5 C6 H6 119.6
C6 C7 C8 121.4(2)
C6 C7 H7 119.3
C8 C7 H7 119.3
C7 C8 C3 117.02(19)
C7 C8 C9 121.76(19)
C3 C8 C9 121.22(18)
C10 C9 C14 116.96(18)
C10 C9 C8 121.48(19)
C14 C9 C8 121.53(18)
C11 C10 C9 121.3(2)
C11 C10 H10 119.3
C9 C10 H10 119.3
C10 C11 C12 120.8(2)
C10 C11 H11 119.6
C12 C11 H11 119.6
C13 C12 C11 119.7(2)
C13 C12 H12 120.2
C11 C12 H12 120.2
C12 C13 C14 119.6(2)
C12 C13 H13 120.2
C14 C13 H13 120.2
C13 C14 C9 121.66(19)
C13 C14 C1 119.73(19)
C9 C14 C1 118.58(18)
C1 N1 S1 106.14(14)
C2 N2 S1 105.88(15)
O2 S1 O1 118.07(12)
O2 S1 N1 111.23(11)
O1 S1 N1 108.94(11)
O2 S1 N2 108.40(11)
O1 S1 N2 109.25(11)
N1 S1 N2 99.29(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.287(3)
C1 C14 1.454(3)
C1 C2 1.510(3)
C2 N2 1.294(3)
C2 C3 1.450(3)
C3 C4 1.397(3)
C3 C8 1.417(3)
C4 C5 1.385(3)
C4 H4 0.95
C5 C6 1.395(4)
C5 H5 0.95
C6 C7 1.388(3)
C6 H6 0.95
C7 C8 1.397(3)
C7 H7 0.95
C8 C9 1.488(3)
C9 C10 1.402(3)
C9 C14 1.411(3)
C10 C11 1.386(3)
C10 H10 0.95
C11 C12 1.389(3)
C11 H11 0.95
C12 C13 1.383(3)
C12 H12 0.95
C13 C14 1.402(3)
C13 H13 0.95
N1 S1 1.6862(19)
N2 S1 1.6910(19)
O1 S1 1.4324(19)
O2 S1 1.416(2)
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
N1 C1 C2 N2 -0.8(3)
C14 C1 C2 N2 178.15(19)
N1 C1 C2 C3 179.53(18)
C14 C1 C2 C3 -1.5(3)
N2 C2 C3 C4 1.0(3)
C1 C2 C3 C4 -179.44(18)
N2 C2 C3 C8 -178.9(2)
C1 C2 C3 C8 0.7(3)
C8 C3 C4 C5 0.8(3)
C2 C3 C4 C5 -179.10(19)
C3 C4 C5 C6 -1.8(3)
C4 C5 C6 C7 1.2(4)
C5 C6 C7 C8 0.4(4)
C6 C7 C8 C3 -1.4(3)
C6 C7 C8 C9 178.4(2)
C4 C3 C8 C7 0.8(3)
C2 C3 C8 C7 -179.30(18)
C4 C3 C8 C9 -179.02(18)
C2 C3 C8 C9 0.9(3)
C7 C8 C9 C10 -3.5(3)
C3 C8 C9 C10 176.38(19)
C7 C8 C9 C14 178.48(19)
C3 C8 C9 C14 -1.7(3)
C14 C9 C10 C11 0.1(3)
C8 C9 C10 C11 -178.1(2)
C9 C10 C11 C12 -0.5(4)
C10 C11 C12 C13 0.2(3)
C11 C12 C13 C14 0.5(3)
C12 C13 C14 C9 -1.0(3)
C12 C13 C14 C1 177.0(2)
C10 C9 C14 C13 0.7(3)
C8 C9 C14 C13 178.81(19)
C10 C9 C14 C1 -177.31(19)
C8 C9 C14 C1 0.8(3)
N1 C1 C14 C13 1.6(3)
C2 C1 C14 C13 -177.31(18)
N1 C1 C14 C9 179.6(2)
C2 C1 C14 C9 0.7(3)
C14 C1 N1 S1 -177.16(17)
C2 C1 N1 S1 1.8(2)
C3 C2 N2 S1 179.03(17)
C1 C2 N2 S1 -0.6(2)
C1 N1 S1 O2 112.11(17)
C1 N1 S1 O1 -116.05(17)
C1 N1 S1 N2 -1.88(17)
C2 N2 S1 O2 -114.76(16)
C2 N2 S1 O1 115.34(16)
C2 N2 S1 N1 1.42(17)
loop_
_cod_related_entry_id
_cod_related_entry_code
_cod_related_entry_database
1 10025448 ChemSpider
2 11850976 PubChem
