#------------------------------------------------------------------------------
#$Date: 2023-03-04 18:31:04 +0200 (Sat, 04 Mar 2023) $
#$Revision: 281305 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/63/7246393.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_7246393
loop_
_publ_author_name
'Li, Chengpeng'
'Kiefel, Milton J.'
_publ_section_title
;
 Facile dione protection to
 benzo[1,2-b:6,5-b']dithiophene-4,5-dione (BDTD) in
 triggering ultraviolet emission - A new member of the emissive
 3,3'-bridged dithiophenes.
;
_journal_issue                   7
_journal_name_full               'RSC advances'
_journal_page_first              4713
_journal_page_last               4720
_journal_paper_doi               10.1039/d2ra07492c
_journal_volume                  13
_journal_year                    2023
_chemical_formula_moiety         'C14 H12 O4 S2'
_chemical_formula_sum            'C14 H12 O4 S2'
_chemical_formula_weight         308.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-06-16
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-06-16 deposited with the CCDC.	2023-01-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.018(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.9393(3)
_cell_length_b                   12.5328(2)
_cell_length_c                   7.40660(10)
_cell_measurement_reflns_used    10967
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      36.1000
_cell_measurement_theta_min      4.2620
_cell_volume                     1286.79(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXD-1997  (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2913
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -93.00 -59.00   1.00    7.50    --  -27.92-178.00 120.00   34
  2  ω    -68.00 -18.00   1.00    7.50    --  -27.92 -38.00 120.00   50
  3  ω    -48.00 -15.00   1.00    7.50    --   29.17 -19.00  90.00   33
  4  ω      5.00  94.00   1.00    7.50    --   29.17  38.00   0.00   89
  5  ω    -41.00  53.00   1.00    7.50    --   29.17 -38.00 -60.00   94
  6  ω     -4.00  63.00   1.00    7.50    --   29.17 -19.00  90.00   67
  7  ω     -4.00 109.00   1.00    7.50    --   29.17  19.00 120.00  113
  8  ω     61.00  87.00   1.00    7.50    --   29.21  38.00-150.00   26
  9  ω   -115.00 -55.00   1.00   10.00    --  -28.27 178.00 150.00   60
 10  ω     -3.00  66.00   1.00   10.00    --   29.21  77.00-150.00   69
 11  ω    -45.00  54.00   1.00   10.00    --   29.21 -38.00  30.00   99
 12  ω    -53.00 -41.00   1.00   10.00    --  -28.27 -77.00   0.00   12
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0374038000
_diffrn_orient_matrix_UB_12      -0.0385536000
_diffrn_orient_matrix_UB_13      0.0035658000
_diffrn_orient_matrix_UB_21      0.0152729000
_diffrn_orient_matrix_UB_22      0.0210829000
_diffrn_orient_matrix_UB_23      -0.0811432000
_diffrn_orient_matrix_UB_31      0.0313744000
_diffrn_orient_matrix_UB_32      0.0356928000
_diffrn_orient_matrix_UB_33      0.0517303000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            17191
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         36.746
_diffrn_reflns_theta_min         3.251
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.424
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73953
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear bluish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   bluish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.592
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ethyl acetate'
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
;
 Flack x determined using 2659 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         6033
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0302
_refine_ls_R_factor_gt           0.0287
_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)+(0.0428P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0732
_refine_ls_wR_factor_ref         0.0748
_reflns_Friedel_coverage         0.947
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.913
_reflns_number_gt                5812
_reflns_number_total             6033
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ra07492c2.cif
_cod_data_source_block           2007a0205
_cod_database_code               7246393
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C14H12O4S2
_chemical_oxdiff_usercomment     'Spot C'
_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.
;
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     35.02
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C14(H14A,H14B), C13(H13A,H13B), C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C2(H2), C1(H1)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.325
_oxdiff_exptl_absorpt_empirical_full_min 0.771
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, 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 0.74026(3) 0.84923(3) 0.32337(4) 0.01953(7) Uani 1 1 d . . . . .
S2 S 0.64426(3) 0.58936(3) 0.19357(5) 0.02346(8) Uani 1 1 d . . . . .
O3 O 0.39588(8) 0.82901(9) 0.22631(15) 0.01966(19) Uani 1 1 d . . . . .
O1 O 0.50652(9) 0.74492(8) 0.67090(14) 0.01934(19) Uani 1 1 d . . . . .
O4 O 0.34517(9) 0.71158(9) 0.43417(16) 0.0228(2) Uani 1 1 d . . . . .
O2 O 0.43334(9) 0.90386(8) 0.59034(14) 0.0204(2) Uani 1 1 d . . . . .
C5 C 0.63011(10) 0.79442(10) 0.35671(18) 0.0154(2) Uani 1 1 d . . . . .
C6 C 0.58004(10) 0.85901(10) 0.46421(18) 0.0148(2) Uani 1 1 d . . . . .
C10 C 0.48653(10) 0.81878(10) 0.52533(17) 0.0148(2) Uani 1 1 d . . . . .
C7 C 0.63034(11) 0.95394(10) 0.51751(18) 0.0176(2) Uani 1 1 d . . . . .
H7 H 0.606297 1.006553 0.589014 0.021 Uiso 1 1 calc R U . . .
C9 C 0.42769(10) 0.75702(10) 0.36926(18) 0.0155(2) Uani 1 1 d . . . . .
C4 C 0.58799(10) 0.69498(10) 0.28688(18) 0.0159(2) Uani 1 1 d . . . . .
C8 C 0.71834(11) 0.95941(12) 0.4518(2) 0.0203(2) Uani 1 1 d . . . . .
H8 H 0.761227 1.015909 0.473859 0.024 Uiso 1 1 calc R U . . .
C3 C 0.49164(10) 0.67428(10) 0.29476(17) 0.0153(2) Uani 1 1 d . . . . .
C11 C 0.29686(12) 0.85238(13) 0.2443(2) 0.0242(3) Uani 1 1 d . . . . .
H11A H 0.261516 0.867770 0.127323 0.029 Uiso 1 1 calc R U . . .
H11B H 0.290884 0.912403 0.325031 0.029 Uiso 1 1 calc R U . . .
C14 C 0.49410(12) 0.80083(14) 0.8345(2) 0.0224(3) Uani 1 1 d . . . . .
H14A H 0.553332 0.835898 0.882800 0.027 Uiso 1 1 calc R U . . .
H14B H 0.473272 0.753106 0.925849 0.027 Uiso 1 1 calc R U . . .
C2 C 0.46351(12) 0.57199(12) 0.2241(2) 0.0210(3) Uani 1 1 d . . . . .
H2 H 0.400925 0.545588 0.218767 0.025 Uiso 1 1 calc R U . . .
C13 C 0.41655(12) 0.88132(13) 0.7739(2) 0.0219(3) Uani 1 1 d . . . . .
H13A H 0.352743 0.851468 0.779636 0.026 Uiso 1 1 calc R U . . .
H13B H 0.423164 0.945201 0.848074 0.026 Uiso 1 1 calc R U . . .
C1 C 0.53881(13) 0.51708(12) 0.1649(2) 0.0254(3) Uani 1 1 d . . . . .
H1 H 0.533742 0.448913 0.115244 0.030 Uiso 1 1 calc R U . . .
C12 C 0.26163(11) 0.75027(14) 0.3242(3) 0.0257(3) Uani 1 1 d . . . . .
H12A H 0.209133 0.764246 0.397155 0.031 Uiso 1 1 calc R U . . .
H12B H 0.240114 0.699560 0.229600 0.031 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 0.0033 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
C8 S1 C5 91.61(7) . . ?
C4 S2 C1 92.01(7) . . ?
C9 O3 C11 106.76(12) . . ?
C14 O1 C10 106.98(11) . . ?
C9 O4 C12 108.19(12) . . ?
C10 O2 C13 108.59(11) . . ?
C6 C5 S1 111.23(10) . . ?
C6 C5 C4 120.08(12) . . ?
C4 C5 S1 128.69(10) . . ?
C5 C6 C10 118.89(11) . . ?
C5 C6 C7 112.91(12) . . ?
C7 C6 C10 127.91(12) . . ?
O1 C10 C6 109.68(11) . . ?
O1 C10 C9 106.58(10) . . ?
O2 C10 O1 107.48(10) . . ?
O2 C10 C6 110.53(11) . . ?
O2 C10 C9 112.04(11) . . ?
C6 C10 C9 110.39(10) . . ?
C6 C7 H7 123.9 . . ?
C8 C7 C6 112.29(13) . . ?
C8 C7 H7 123.9 . . ?
O3 C9 C10 109.65(11) . . ?
O3 C9 C3 108.23(11) . . ?
O4 C9 O3 107.88(11) . . ?
O4 C9 C10 109.46(11) . . ?
O4 C9 C3 112.38(11) . . ?
C3 C9 C10 109.19(11) . . ?
C5 C4 S2 128.33(11) . . ?
C3 C4 S2 111.12(10) . . ?
C3 C4 C5 120.52(12) . . ?
S1 C8 H8 124.0 . . ?
C7 C8 S1 111.95(11) . . ?
C7 C8 H8 124.0 . . ?
C4 C3 C9 120.19(12) . . ?
C4 C3 C2 112.75(13) . . ?
C2 C3 C9 127.05(13) . . ?
O3 C11 H11A 111.2 . . ?
O3 C11 H11B 111.2 . . ?
O3 C11 C12 102.65(12) . . ?
H11A C11 H11B 109.1 . . ?
C12 C11 H11A 111.2 . . ?
C12 C11 H11B 111.2 . . ?
O1 C14 H14A 111.2 . . ?
O1 C14 H14B 111.2 . . ?
O1 C14 C13 102.83(11) . . ?
H14A C14 H14B 109.1 . . ?
C13 C14 H14A 111.2 . . ?
C13 C14 H14B 111.2 . . ?
C3 C2 H2 123.8 . . ?
C1 C2 C3 112.36(14) . . ?
C1 C2 H2 123.8 . . ?
O2 C13 C14 103.34(12) . . ?
O2 C13 H13A 111.1 . . ?
O2 C13 H13B 111.1 . . ?
C14 C13 H13A 111.1 . . ?
C14 C13 H13B 111.1 . . ?
H13A C13 H13B 109.1 . . ?
S2 C1 H1 124.1 . . ?
C2 C1 S2 111.76(11) . . ?
C2 C1 H1 124.1 . . ?
O4 C12 C11 103.34(12) . . ?
O4 C12 H12A 111.1 . . ?
O4 C12 H12B 111.1 . . ?
C11 C12 H12A 111.1 . . ?
C11 C12 H12B 111.1 . . ?
H12A C12 H12B 109.1 . . ?
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 C5 1.7233(14) . ?
S1 C8 1.7223(16) . ?
S2 C4 1.7201(13) . ?
S2 C1 1.7206(18) . ?
O3 C9 1.4259(16) . ?
O3 C11 1.431(2) . ?
O1 C10 1.4262(16) . ?
O1 C14 1.4259(18) . ?
O4 C9 1.4123(17) . ?
O4 C12 1.434(2) . ?
O2 C10 1.4118(16) . ?
O2 C13 1.4315(19) . ?
C5 C6 1.3759(18) . ?
C5 C4 1.4497(19) . ?
C6 C10 1.511(2) . ?
C6 C7 1.4159(18) . ?
C10 C9 1.5522(18) . ?
C7 H7 0.9300 . ?
C7 C8 1.368(2) . ?
C9 C3 1.5092(19) . ?
C4 C3 1.3751(19) . ?
C8 H8 0.9300 . ?
C3 C2 1.4242(19) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.513(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C13 1.512(2) . ?
C2 H2 0.9300 . ?
C2 C1 1.365(2) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C1 H1 0.9300 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
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 C5 C6 C10 -173.44(9) . . . . ?
S1 C5 C6 C7 0.91(15) . . . . ?
S1 C5 C4 S2 15.8(2) . . . . ?
S1 C5 C4 C3 -166.08(11) . . . . ?
S2 C4 C3 C9 -179.00(10) . . . . ?
S2 C4 C3 C2 -0.13(15) . . . . ?
O3 C9 C3 C4 84.46(15) . . . . ?
O3 C9 C3 C2 -94.22(16) . . . . ?
O3 C11 C12 O4 32.48(16) . . . . ?
O1 C10 C9 O3 173.60(11) . . . . ?
O1 C10 C9 O4 55.44(13) . . . . ?
O1 C10 C9 C3 -67.97(13) . . . . ?
O1 C14 C13 O2 -31.63(16) . . . . ?
O4 C9 C3 C4 -156.51(12) . . . . ?
O4 C9 C3 C2 24.80(19) . . . . ?
O2 C10 C9 O3 56.30(14) . . . . ?
O2 C10 C9 O4 -61.86(14) . . . . ?
O2 C10 C9 C3 174.73(11) . . . . ?
C5 S1 C8 C7 0.14(12) . . . . ?
C5 C6 C10 O1 77.54(15) . . . . ?
C5 C6 C10 O2 -164.13(12) . . . . ?
C5 C6 C10 C9 -39.61(16) . . . . ?
C5 C6 C7 C8 -0.82(17) . . . . ?
C5 C4 C3 C9 2.56(19) . . . . ?
C5 C4 C3 C2 -178.57(13) . . . . ?
C6 C5 C4 S2 -164.73(11) . . . . ?
C6 C5 C4 C3 13.4(2) . . . . ?
C6 C10 C9 O3 -67.35(13) . . . . ?
C6 C10 C9 O4 174.49(10) . . . . ?
C6 C10 C9 C3 51.08(13) . . . . ?
C6 C7 C8 S1 0.35(16) . . . . ?
C10 O1 C14 C13 30.99(16) . . . . ?
C10 O2 C13 C14 21.03(15) . . . . ?
C10 C6 C7 C8 172.91(12) . . . . ?
C10 C9 C3 C4 -34.85(16) . . . . ?
C10 C9 C3 C2 146.46(13) . . . . ?
C7 C6 C10 O1 -95.86(15) . . . . ?
C7 C6 C10 O2 22.47(18) . . . . ?
C7 C6 C10 C9 146.99(13) . . . . ?
C9 O3 C11 C12 -31.06(15) . . . . ?
C9 O4 C12 C11 -22.26(16) . . . . ?
C9 C3 C2 C1 179.06(14) . . . . ?
C4 S2 C1 C2 0.20(14) . . . . ?
C4 C5 C6 C10 6.98(19) . . . . ?
C4 C5 C6 C7 -178.67(12) . . . . ?
C4 C3 C2 C1 0.29(18) . . . . ?
C8 S1 C5 C6 -0.60(11) . . . . ?
C8 S1 C5 C4 178.94(13) . . . . ?
C3 C2 C1 S2 -0.31(18) . . . . ?
C11 O3 C9 O4 18.20(15) . . . . ?
C11 O3 C9 C10 -100.94(13) . . . . ?
C11 O3 C9 C3 140.04(12) . . . . ?
C14 O1 C10 O2 -18.82(15) . . . . ?
C14 O1 C10 C6 101.38(13) . . . . ?
C14 O1 C10 C9 -139.10(12) . . . . ?
C13 O2 C10 O1 -2.36(15) . . . . ?
C13 O2 C10 C6 -122.03(13) . . . . ?
C13 O2 C10 C9 114.40(12) . . . . ?
C1 S2 C4 C5 178.25(13) . . . . ?
C1 S2 C4 C3 -0.03(11) . . . . ?
C12 O4 C9 O3 3.49(16) . . . . ?
C12 O4 C9 C10 122.75(12) . . . . ?
C12 O4 C9 C3 -115.75(13) . . . . ?
