Study of a carbazole–bromobenzothiadiazole derived fluorescent molecular rotor: crystal structure, redox activity, and solvatofluorochromic effects
Chernick, Erin T.; Abdollahi, Maryam F.; Tabasi, Zahra A.; Junge, Marc J.; Zhao, Yuming; New Journal of Chemistry 46 (2022) 572–581; doi:10.1039/D1NJ04274B

data_7061093
_publ_section_title
;
 Study of a carbazole--bromobenzothiadiazole derived fluorescent molecular
 rotor: crystal structure, redox activity, and solvatofluorochromic
 effects
;
_journal_issue                   2
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              572
_journal_page_last               581
_journal_paper_doi               10.1039/D1NJ04274B
_journal_volume                  46
_journal_year                    2022
_chemical_formula_moiety         'C29 H18 Br N3 S2'
_chemical_formula_sum            'C29 H18 Br N3 S2'
_chemical_formula_weight         552.49
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-06-29
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-07-05 deposited with the CCDC.	2021-12-02 downloaded from the CCDC.
;
_cell_angle_alpha                94.9790(10)
_cell_angle_beta                 109.1850(10)
_cell_angle_gamma                114.5180(10)
_cell_formula_units_Z            2
_cell_length_a                   9.74830(10)
_cell_length_b                   11.0899(2)
_cell_length_c                   13.28450(10)
_cell_measurement_reflns_used    14350
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      79.6110
_cell_measurement_theta_min      3.6240
_cell_volume                     1191.75(3)
_computing_cell_refinement       'CrysAlisPro 1.171.41.111a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.111a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.111a (Rigaku OD, 2021)'
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.976
_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     29.00  84.00   0.50    0.05    --   49.43  77.00 -30.00  110
  2  \w     29.00 121.00   0.50    0.05    --   49.43  77.00-150.00  184
  3  \w     29.00 121.00   0.50    0.05    --   49.43  77.00  60.00  184
  4  \w     29.00 121.00   0.50    0.05    --   49.43  77.00 150.00  184
  5  \w     41.00 105.00   0.50    0.07    --  111.50 -94.00  90.00  128
  6  \w     41.00 117.00   0.50    0.07    --  111.50-132.00 121.00  152
  7  \w     38.00  99.00   0.50    0.05    --   49.43-132.00 121.00  122
  8  \w     41.00 111.00   0.50    0.07    --  111.50-125.00  30.00  140
  9  \w     41.00 111.00   0.50    0.07    --  111.50-125.00   0.00  140
 10  \w     41.00 111.00   0.50    0.07    --  111.50-125.00 -30.00  140
 11  \w     41.00 119.00   0.50    0.07    --  111.50-136.00 -55.00  156
 12  \w     41.00 111.00   0.50    0.07    --  111.50-125.00 -90.00  140
 13  \w     41.00 105.00   0.50    0.07    --  111.50 -94.00-180.00  128
 14  \w     41.00 101.00   0.50    0.05    --   49.43-136.00 -55.00  120
 15  \w     41.00 111.00   0.50    0.07    --  111.50-125.00  60.00  140
 16  \w     41.00 105.00   0.50    0.07    --  111.50 -94.00 120.00  128
 17  \w     41.00 105.00   0.50    0.07    --  111.50 -94.00 150.00  128
 18  \w     41.00  79.00   0.50    0.07    --  111.50 -61.00 -30.00   76
 19  \w     41.00  79.00   0.50    0.07    --  111.50 -61.00-120.00   76
 20  \w     41.00  79.00   0.50    0.07    --  111.50 -61.00  60.00   76
 21  \w     41.00  79.00   0.50    0.07    --  111.50 -61.00  30.00   76
 22  \w     41.00  79.00   0.50    0.07    --  111.50 -61.00 -60.00   76
 23  \w     41.00  79.00   0.50    0.07    --  111.50 -61.00-180.00   76
 24  \w     41.00  79.00   0.50    0.07    --  111.50 -61.00   0.00   76
 25  \w     41.00  79.00   0.50    0.07    --  111.50 -61.00 150.00   76
 26  \w     88.00 178.00   0.50    0.07    --  111.50 136.00   8.00  180
 27  \w     91.00 178.00   0.50    0.07    --  111.50 132.00-169.00  174
 28  \w     91.00 178.00   0.50    0.07    --  111.50  77.00 -90.00  174
 29  \w    104.00 178.00   0.50    0.07    --  111.50  30.00-180.00  148
 30  \w    102.00 178.00   0.50    0.07    --  111.50  45.00 -60.00  152
 31  \w    104.00 178.00   0.50    0.07    --  111.50  15.00-150.00  148
 32  \w    102.00 178.00   0.50    0.07    --  111.50  45.00   0.00  152
 33  \w    102.00 178.00   0.50    0.07    --  111.50  45.00  60.00  152
 34  \w    104.00 178.00   0.50    0.07    --  111.50  15.00 120.00  148
 35  \w    104.00 178.00   0.50    0.07    --  111.50  30.00 150.00  148
 36  \w    -16.00  24.00   0.50    0.05    --  -49.43  19.00 -90.00   80
 37  \w    -16.00  24.00   0.50    0.05    --  -49.43  19.00-120.00   80
 38  \w    -16.00  24.00   0.50    0.05    --  -49.43  19.00-180.00   80
 39  \w    -16.00  24.00   0.50    0.05    --  -49.43  19.00-150.00   80
 40  \w    -16.00  24.00   0.50    0.05    --  -49.43  19.00 -60.00   80
 41  \w    -16.00  24.00   0.50    0.05    --  -49.43  19.00 -30.00   80
 42  \w    -16.00  24.00   0.50    0.05    --  -49.43  19.00  30.00   80
 43  \w    -16.00  24.00   0.50    0.05    --  -49.43  19.00 150.00   80
 44  \w    -94.00 -19.00   0.50    0.07    --  -90.00 136.00   8.00  150
 45  \w    -94.00 -19.00   0.50    0.05    --  -49.43 136.00   8.00  150
 46  \w    -91.00 -17.00   0.50    0.05    --  -49.43 132.00-169.00  148
 47  \w    -65.00 -18.00   0.50    0.07    --  -90.00  61.00 -30.00   94
 48  \w   -162.00 -82.00   0.50    0.07    --  -90.00 -15.00 150.00  160
 49  \w   -121.00 -66.00   0.50    0.05    --  -49.43-136.00 -55.00  110
 50  \w   -160.00 -66.00   0.50    0.07    --  -90.00-136.00 -55.00  188
 51  \w   -121.00 -29.00   0.50    0.05    --  -49.43 -77.00 -90.00  184
 52  \w   -121.00 -37.00   0.50    0.05    --  -49.43 -57.00 -30.00  168
 53  \w   -161.00 -69.00   0.50    0.07    --  -90.00-132.00 121.00  184
 54  \w   -121.00 -69.00   0.50    0.05    --  -49.43-132.00 121.00  104
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0443969000
_diffrn_orient_matrix_UB_12      0.0237939000
_diffrn_orient_matrix_UB_13      -0.1163870000
_diffrn_orient_matrix_UB_21      0.0921633000
_diffrn_orient_matrix_UB_22      0.1562271000
_diffrn_orient_matrix_UB_23      0.0511800000
_diffrn_orient_matrix_UB_31      0.1597822000
_diffrn_orient_matrix_UB_32      0.0049888000
_diffrn_orient_matrix_UB_33      -0.0011253000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            30336
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.816
_diffrn_reflns_theta_min         3.648
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.175
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49606
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.111a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.540
_exptl_crystal_description       irregular
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.075
_refine_diff_density_max         0.913
_refine_diff_density_min         -1.168
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         5068
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0460
_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/[\s^2^(Fo^2^)+(0.0538P)^2^+0.8586P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1191
_refine_ls_wR_factor_ref         0.1241
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4322
_reflns_number_total             5068
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1nj04274b2.cif
_cod_data_source_block           carbazolederiv
_cod_depositor_comments          'Adding full bibliography for 7061093.cif.'
_cod_database_code               7061093
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C29H18BrN3S2
_shelx_estimated_absorpt_t_max   0.745
_shelx_estimated_absorpt_t_min   0.358
_reflns_odcompleteness_completeness 99.59
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C8(H8), C13(H13), C14(H14), C16(H16), C17(H17), C19(H19),
 C20(H20), C21(H21), C22(H22), C25(H25), C26(H26), C27(H27), C28(H28)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_shelx_res_checksum              16738
_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 1.536
_oxdiff_exptl_absorpt_empirical_full_min 0.628