#------------------------------------------------------------------------------
#$Date: 2020-04-04 07:24:41 +0300 (Sat, 04 Apr 2020) $
#$Revision: 250097 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/81/4038114.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_4038114
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      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-08-01
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 94.214(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.424(9)
_cell_length_b                   9.680(9)
_cell_length_c                   13.829(10)
_cell_measurement_reflns_used    9978
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.561
_cell_measurement_theta_min      2.545
_cell_volume                     1258.1(19)
_computing_cell_refinement       'SAINT V8.38A (Madison, 2016)'
_computing_data_collection       'Bruker APEX2 software'
_computing_data_reduction        'SAINT V8.38A (Madison, 2016)'
_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      99.99
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'fixed-chi two circle goniometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            22528
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.481
_diffrn_reflns_theta_min         2.531
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           50
_diffrn_source_type              'Incoatec Mo I\ms'
_diffrn_source_voltage           0.6
_exptl_absorpt_coefficient_mu    0.415
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5877
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1360 before and 0.0558 after correction. The Ratio of minimum to maximum transmission is 0.7882. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_recrystallization_method
'The material was recrystallised from a mixture of DCM and methanol  by solvent layering'
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.470
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2875
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0339
_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)+(0.0507P)²+0.7538P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0919
_refine_ls_wR_factor_ref         0.0947
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2621
_reflns_number_total             2875
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c00567_si_002.cif
_cod_data_source_block           esser_jw231_f3_0m_a
_cod_depositor_comments
'Adding full bibliography for 4038114--4038124.cif.'
_cod_original_cell_volume        1258.2(18)
_cod_database_code               4038114
_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.
;
_shelx_estimated_absorpt_t_max   0.960
_shelx_estimated_absorpt_t_min   0.835
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C11(H11), C12(H12), C13(H13), C14(H14)
;
_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+1/2, -z+1/2'
'-x, -y, -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 0.55164(4) 0.44043(4) 0.39117(3) 0.01960(12) Uani 1 1 d . . . . .
S2 S 0.74100(4) 0.19492(4) 0.38688(3) 0.02146(12) Uani 1 1 d . . . . .
O1 O 0.81904(12) 0.43809(12) 0.54781(9) 0.0257(3) Uani 1 1 d . . . . .
O2 O 0.41767(12) 0.15147(12) 0.46367(8) 0.0245(3) Uani 1 1 d . . . . .
C1 C 0.63057(16) 0.29844(15) 0.46297(10) 0.0170(3) Uani 1 1 d . . . . .
C2 C 0.72575(16) 0.35317(16) 0.55204(11) 0.0184(3) Uani 1 1 d . . . . .
C3 C 0.67855(15) 0.28152(15) 0.63939(11) 0.0174(3) Uani 1 1 d . . . . .
C4 C 0.73644(16) 0.29097(16) 0.73556(11) 0.0208(3) Uani 1 1 d . . . . .
H4 H 0.817139 0.347208 0.752290 0.025 Uiso 1 1 calc R . . . .
C5 C 0.67151(17) 0.21501(17) 0.80579(11) 0.0226(3) Uani 1 1 d . . . . .
H5 H 0.709423 0.218523 0.871321 0.027 Uiso 1 1 calc R . . . .
C6 C 0.55048(17) 0.13306(17) 0.78111(12) 0.0224(3) Uani 1 1 d . . . . .
H6 H 0.507240 0.083512 0.830447 0.027 Uiso 1 1 calc R . . . .
C7 C 0.49318(16) 0.12359(16) 0.68524(11) 0.0202(3) Uani 1 1 d . . . . .
H7 H 0.411846 0.068171 0.668569 0.024 Uiso 1 1 calc R . . . .
C8 C 0.55952(15) 0.19844(15) 0.61449(11) 0.0168(3) Uani 1 1 d . . . . .
C9 C 0.51873(16) 0.20549(15) 0.50834(11) 0.0175(3) Uani 1 1 d . . . . .
C10 C 0.65491(16) 0.24697(16) 0.27476(11) 0.0191(3) Uani 1 1 d . . . . .
C11 C 0.67461(18) 0.17886(18) 0.18729(12) 0.0257(3) Uani 1 1 d . . . . .
H11 H 0.730367 0.097149 0.186713 0.031 Uiso 1 1 calc R . . . .
C12 C 0.61086(19) 0.2331(2) 0.10074(12) 0.0299(4) Uani 1 1 d . . . . .
H12 H 0.623279 0.187597 0.041062 0.036 Uiso 1 1 calc R . . . .
C13 C 0.5296(2) 0.35273(19) 0.10152(12) 0.0292(4) Uani 1 1 d . . . . .
H13 H 0.488534 0.389474 0.042207 0.035 Uiso 1 1 calc R . . . .
C14 C 0.50775(18) 0.41974(18) 0.18897(12) 0.0244(3) Uani 1 1 d . . . . .
H14 H 0.451200 0.500957 0.189328 0.029 Uiso 1 1 calc R . . . .
C15 C 0.57017(16) 0.36566(16) 0.27577(11) 0.0184(3) 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 0.0000 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
C15 S1 C1 96.85(9) . . ?
C10 S2 C1 95.99(9) . . ?
S1 C1 S2 109.03(9) . . ?
C2 C1 S1 111.20(11) . . ?
C2 C1 S2 108.72(11) . . ?
C9 C1 S1 113.28(11) . . ?
C9 C1 S2 110.26(11) . . ?
C9 C1 C2 104.21(12) . . ?
O1 C2 C1 124.77(14) . . ?
O1 C2 C3 128.18(14) . . ?
C3 C2 C1 107.05(13) . . ?
C4 C3 C2 128.33(15) . . ?
C8 C3 C2 110.44(13) . . ?
C8 C3 C4 121.23(14) . . ?
C5 C4 C3 117.76(15) . . ?
C4 C5 C6 121.09(15) . . ?
C7 C6 C5 121.05(15) . . ?
C6 C7 C8 117.87(15) . . ?
C3 C8 C9 111.04(13) . . ?
C7 C8 C3 121.00(14) . . ?
C7 C8 C9 127.95(14) . . ?
O2 C9 C1 125.03(14) . . ?
O2 C9 C8 128.07(14) . . ?
C8 C9 C1 106.90(12) . . ?
C11 C10 S2 122.74(14) . . ?
C15 C10 S2 116.74(12) . . ?
C15 C10 C11 120.43(15) . . ?
C12 C11 C10 119.04(17) . . ?
C13 C12 C11 120.50(16) . . ?
C12 C13 C14 120.60(16) . . ?
C15 C14 C13 119.22(17) . . ?
C10 C15 S1 115.99(12) . . ?
C14 C15 S1 123.82(13) . . ?
C14 C15 C10 120.18(15) . . ?
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 1.8220(18) . ?
S1 C15 1.7726(18) . ?
S2 C1 1.8318(17) . ?
S2 C10 1.7696(18) . ?
O1 C2 1.208(2) . ?
O2 C9 1.215(2) . ?
C1 C2 1.562(2) . ?
C1 C9 1.553(2) . ?
C2 C3 1.489(2) . ?
C3 C4 1.403(2) . ?
C3 C8 1.403(2) . ?
C4 C5 1.395(2) . ?
C5 C6 1.411(3) . ?
C6 C7 1.397(2) . ?
C7 C8 1.401(2) . ?
C8 C9 1.491(2) . ?
C10 C11 1.402(2) . ?
C10 C15 1.400(2) . ?
C11 C12 1.401(3) . ?
C12 C13 1.389(3) . ?
C13 C14 1.401(3) . ?
C14 C15 1.399(2) . ?
