#------------------------------------------------------------------------------
#$Date: 2020-04-04 07:24:41 +0300 (Sat, 04 Apr 2020) $
#$Revision: 250097 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/81/4038115.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_4038115
loop_
_publ_author_name
'Wössner, Jan S'
'Esser, Birgit'
_publ_section_title
;
 Spiroconjugated Donor-σ-Acceptor Charge-Transfer Dyes: Effect of the
 π-Subsystems on the Optoelectronic Properties.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5048
_journal_page_last               5057
_journal_paper_doi               10.1021/acs.joc.0c00567
_journal_volume                  85
_journal_year                    2020
_chemical_formula_moiety         'C15 H8 O2 S2'
_chemical_formula_sum            'C15 H8 O2 S2'
_chemical_formula_weight         284.33
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-10-22
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.3775(11)
_cell_length_b                   7.2583(6)
_cell_length_c                   11.0501(9)
_cell_measurement_reflns_used    1088
_cell_measurement_temperature    100
_cell_measurement_theta_max      99
_cell_measurement_theta_min      1
_cell_volume                     1233.35(17)
_computing_data_collection       'Bruker APEX2 software'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'Image Plate'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Rigaku IP'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku Spider'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0610
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15119
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.474
_diffrn_reflns_theta_min         3.228
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           50
_diffrn_source_target            Mo
_diffrn_source_type              'Incoatec Mo I\ms'
_diffrn_source_voltage           0.6
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.424
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6680
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
'Empirical Absorption Correction   March    2001 T Higashi'
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.531
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_recrystallization_method
'The material was recrystallised from a mixture of DCM and cyclohexane  by solvent layering'
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.489
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     103
_refine_ls_number_reflns         1525
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.131
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0475
_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)+(0.0638P)²+0.9273P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1193
_refine_ls_wR_factor_ref         0.1243
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1375
_reflns_number_total             1525
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c00567_si_002.cif
_cod_data_source_block           esser-jw273_a
_cod_depositor_comments
'Adding full bibliography for 4038114--4038124.cif.'
_cod_database_code               4038115
_shelx_shelxl_version_number     2018/3
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C8(H8), C9(H9), C10(H10), C11(H11)
;
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems 800'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, 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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.57113(4) 0.45351(7) 0.33536(5) 0.0239(2) Uani 1 1 d . . . . .
O1 O 0.73857(14) 0.250000 0.2131(2) 0.0267(5) Uani 1 2 d S T P . .
C1 C 0.61829(13) 0.3464(3) 0.46334(19) 0.0214(5) Uani 1 1 d . . . . .
C2 C 0.65041(15) 0.4429(3) 0.5620(2) 0.0242(5) Uani 1 1 d . . . . .
H2 H 0.651871 0.570995 0.561206 0.029 Uiso 1 1 calc R . . . .
O2 O 0.70191(15) 0.250000 -0.0457(2) 0.0303(5) Uani 1 2 d S T P . .
C3 C 0.68041(15) 0.3460(3) 0.66227(19) 0.0250(5) Uani 1 1 d . . . . .
H3 H 0.700584 0.409707 0.729683 0.030 Uiso 1 1 calc R . . . .
C4 C 0.57975(19) 0.250000 0.2389(3) 0.0212(6) Uani 1 2 d S T P . .
C5 C 0.6665(2) 0.250000 0.1697(3) 0.0209(6) Uani 1 2 d S T P . .
C8 C 0.4999(2) 0.250000 -0.0822(3) 0.0252(7) Uani 1 2 d S T P . .
H8 H 0.525389 0.250000 -0.158534 0.030 Uiso 1 2 calc RS T P . .
C7 C 0.5512(2) 0.250000 0.0231(3) 0.0226(6) Uani 1 2 d S T P . .
C6 C 0.6459(2) 0.250000 0.0326(3) 0.0231(6) Uani 1 2 d S T P . .
C9 C 0.4105(2) 0.250000 -0.0691(3) 0.0264(7) Uani 1 2 d S T P . .
H9 H 0.375257 0.250000 -0.137434 0.032 Uiso 1 2 calc RS T P . .
C10 C 0.3723(2) 0.250000 0.0465(3) 0.0259(7) Uani 1 2 d S T P . .
H10 H 0.312063 0.250000 0.053364 0.031 Uiso 1 2 calc RS T P . .
C11 C 0.4230(2) 0.250000 0.1508(3) 0.0248(7) Uani 1 2 d S T P . .
H11 H 0.397485 0.250000 0.227103 0.030 Uiso 1 2 calc RS T P . .
C12 C 0.5126(2) 0.250000 0.1378(3) 0.0213(6) Uani 1 2 d S T P . .
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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 S1 C4 94.67(11) . . ?
C1 C1 S1 116.07(7) 7_565 . ?
C2 C1 S1 123.54(17) . . ?
C2 C1 C1 120.33(13) . 7_565 ?
C1 C2 H2 120.4 . . ?
C1 C2 C3 119.3(2) . . ?
C3 C2 H2 120.4 . . ?
C2 C3 C3 120.38(13) . 7_565 ?
C2 C3 H3 119.8 . . ?
C3 C3 H3 119.8 7_565 . ?
S1 C4 S1 107.96(16) 7_565 . ?
C5 C4 S1 110.67(13) . . ?
C5 C4 S1 110.67(13) . 7_565 ?
C12 C4 S1 112.30(13) . 7_565 ?
C12 C4 S1 112.30(13) . . ?
C12 C4 C5 102.9(2) . . ?
O1 C5 C4 126.8(3) . . ?
O1 C5 C6 125.2(3) . . ?
C4 C5 C6 108.0(2) . . ?
C7 C8 H8 121.0 . . ?
C9 C8 H8 121.0 . . ?
C9 C8 C7 118.1(3) . . ?
C8 C7 C6 128.2(3) . . ?
C12 C7 C8 120.8(3) . . ?
C12 C7 C6 110.9(3) . . ?
O2 C6 C5 123.3(3) . . ?
O2 C6 C7 130.8(3) . . ?
C7 C6 C5 105.9(3) . . ?
C8 C9 H9 119.6 . . ?
C8 C9 C10 120.7(3) . . ?
C10 C9 H9 119.6 . . ?
C9 C10 H10 119.4 . . ?
C11 C10 C9 121.2(3) . . ?
C11 C10 H10 119.4 . . ?
C10 C11 H11 120.9 . . ?
C12 C11 C10 118.1(3) . . ?
C12 C11 H11 120.9 . . ?
C7 C12 C4 112.2(3) . . ?
C11 C12 C4 126.8(3) . . ?
C11 C12 C7 121.0(3) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.769(2) . ?
S1 C4 1.8263(18) . ?
O1 C5 1.207(4) . ?
C1 C1 1.399(4) 7_565 ?
C1 C2 1.387(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.391(3) . ?
O2 C6 1.220(4) . ?
C3 C3 1.394(5) 7_565 ?
C3 H3 0.9300 . ?
C4 C5 1.538(4) . ?
C4 C12 1.521(4) . ?
C5 C6 1.549(4) . ?
C8 H8 0.9300 . ?
C8 C7 1.405(4) . ?
C8 C9 1.382(5) . ?
C7 C6 1.461(4) . ?
C7 C12 1.400(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.405(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.392(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.385(4) . ?
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C1 C2 C3 175.27(16) . . . . ?
S1 C4 C5 O1 59.82(13) . . . . ?
S1 C4 C5 O1 -59.82(13) 7_565 . . . ?
S1 C4 C5 C6 120.18(13) 7_565 . . . ?
S1 C4 C5 C6 -120.18(13) . . . . ?
S1 C4 C12 C7 -119.05(14) 7_565 . . . ?
S1 C4 C12 C7 119.05(14) . . . . ?
S1 C4 C12 C11 60.95(14) 7_565 . . . ?
S1 C4 C12 C11 -60.95(14) . . . . ?
O1 C5 C6 O2 0.000(0) . . . . ?
O1 C5 C6 C7 180.000(0) . . . . ?
C1 S1 C4 S1 30.46(15) . . . 7_565 ?
C1 S1 C4 C5 -90.79(18) . . . . ?
C1 S1 C4 C12 154.79(19) . . . . ?
C1 C1 C2 C3 -1.7(3) 7_565 . . . ?
C1 C2 C3 C3 1.7(3) . . . 7_565 ?
C4 S1 C1 C1 -19.39(10) . . . 7_565 ?
C4 S1 C1 C2 163.5(2) . . . . ?
C4 C5 C6 O2 180.000(0) . . . . ?
C4 C5 C6 C7 0.0 . . . . ?
C5 C4 C12 C7 0.000(0) . . . . ?
C5 C4 C12 C11 180.000(0) . . . . ?
C8 C7 C6 O2 0.000(0) . . . . ?
C8 C7 C6 C5 180.000(0) . . . . ?
C8 C7 C12 C4 180.000(0) . . . . ?
C8 C7 C12 C11 0.000(0) . . . . ?
C8 C9 C10 C11 0.000(0) . . . . ?
C7 C8 C9 C10 0.0 . . . . ?
C6 C7 C12 C4 0.0 . . . . ?
C6 C7 C12 C11 180.0 . . . . ?
C9 C8 C7 C6 180.0 . . . . ?
C9 C8 C7 C12 0.000(0) . . . . ?
C9 C10 C11 C12 0.000(0) . . . . ?
C10 C11 C12 C4 180.000(0) . . . . ?
C10 C11 C12 C7 0.000(0) . . . . ?
C12 C4 C5 O1 180.000(0) . . . . ?
C12 C4 C5 C6 0.000(0) . . . . ?
C12 C7 C6 O2 180.000(0) . . . . ?
C12 C7 C6 C5 0.000(0) . . . . ?
