Facile dione protection to benzo[1,2-<i>b</i>:6,5-<i>b</i>']dithiophene-4,5-dione (BDTD) in triggering ultraviolet emission - A new member of the emissive 3,3'-bridged dithiophenes.
Li, Chengpeng; Kiefel, Milton J.; RSC advances 13 (2023) 4713–4720; doi:10.1039/d2ra07492c

data_7246393
_publ_section_title
;
 Facile dione protection to
 benzo[1,2-<i>b</i>:6,5-<i>b</i>']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  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -93.00 -59.00   1.00    7.50    --  -27.92-178.00 120.00   34
  2  \w    -68.00 -18.00   1.00    7.50    --  -27.92 -38.00 120.00   50
  3  \w    -48.00 -15.00   1.00    7.50    --   29.17 -19.00  90.00   33
  4  \w      5.00  94.00   1.00    7.50    --   29.17  38.00   0.00   89
  5  \w    -41.00  53.00   1.00    7.50    --   29.17 -38.00 -60.00   94
  6  \w     -4.00  63.00   1.00    7.50    --   29.17 -19.00  90.00   67
  7  \w     -4.00 109.00   1.00    7.50    --   29.17  19.00 120.00  113
  8  \w     61.00  87.00   1.00    7.50    --   29.21  38.00-150.00   26
  9  \w   -115.00 -55.00   1.00   10.00    --  -28.27 178.00 150.00   60
 10  \w     -3.00  66.00   1.00   10.00    --   29.21  77.00-150.00   69
 11  \w    -45.00  54.00   1.00   10.00    --   29.21 -38.00  30.00   99
 12  \w    -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       '\w 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/[\s^2^(Fo^2^)+(0.0428P)^2^] where P=(Fo^2^+2Fc^2^)/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 > 2\s(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'
_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)
;
_shelx_res_checksum              31032
_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