Modulation of Δ<i>E</i><sub>ST</sub> and room temperature phosphorescence in carbazole derivatives.
Barhate, Komal Vasant; Wadawale, Amey P.; Chandrakumar, K. R. S.; Agarwal, Neeraj; Chemical communications (Cambridge, England) 60 (2024) 1408–1411; doi:10.1039/d3cc05119f

data_7132565
_publ_section_title
;
 Modulation of &#x394;<i>E</i><sub>ST</sub> and room temperature
 phosphorescence in carbazole derivatives.
;
_journal_issue                   11
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1408
_journal_page_last               1411
_journal_paper_doi               10.1039/d3cc05119f
_journal_volume                  60
_journal_year                    2024
_chemical_formula_sum            'C32 H21 F2 N O'
_chemical_formula_weight         473.50
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2023-10-05 deposited with the CCDC.	2024-01-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.3830(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.54460(10)
_cell_length_b                   21.9876(5)
_cell_length_c                   7.50510(10)
_cell_measurement_reflns_used    42240
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      77.2410
_cell_measurement_theta_min      3.1090
_cell_volume                     2352.93(6)
_computing_cell_refinement       'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_molecular_graphics    'ORTEP-3 for windws'
_computing_publication_material  'WinGX 2021.3'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.941
_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    -26.00  27.20   0.40    0.35    --  -48.16  19.00-108.00  133
  2  \w    -13.00  34.20   0.40    0.35    --   18.00  94.00 -36.04  118
  3  \w     12.00  40.80   0.40    0.35    --   42.00  92.00  -5.90   72
  4  \w     36.00  71.20   0.40    0.35    --   58.00  76.00 -25.32   88
  5  \w     41.00  71.00   0.40    0.35    --   62.00  73.00 -46.36   75
  6  \w     77.00 121.00   0.40    0.35    --   54.00  77.00 -97.00  110
  7  \w     95.00 177.80   0.40    1.50    --  107.75  19.00-108.00  207
  8  \w    145.00 177.00   0.40    1.50    --  107.75  61.00 -60.00   80
  9  \w    134.00 160.00   0.40    1.50    --  107.75  61.00  30.00   65
 10  \w    142.00 178.00   0.40    1.50    --  107.75  77.00  90.00   90
 11  \w    140.00 167.20   0.40    1.50    --  107.75  77.00 120.00   68
 12  \w    142.00 168.00   0.40    1.50    --  107.75  61.00 150.00   65
 13  \w    102.00 128.00   0.40    0.35    --   70.00  75.00  78.89   65
 14  \w     91.00 125.00   0.40    0.35    --   54.00  79.00 154.75   85
 15  \w     76.00 101.20   0.40    1.50    --   98.00  76.00  66.65   63
 16  \w     91.00 124.20   0.40    1.50    --  107.75  61.00  30.00   83
 17  \w    120.00 146.00   0.40    1.50    --  107.75  77.00   0.00   65
 18  \w    125.00 151.00   0.40    1.50    --  107.75  77.00 -30.00   65
 19  \w    122.00 151.20   0.40    1.50    --  107.75  77.00 -90.00   73
 20  \w    137.00 169.00   0.40    1.50    --  107.75  61.00-150.00   80
 21  \w    144.00 170.00   0.40    1.50    --  107.75  77.00-180.00   65
 22  \w    130.00 156.00   0.40    1.50    --  107.75  61.00-120.00   65
 23  \w    122.00 166.00   0.40    1.50    --  107.75  77.00-120.00  110
 24  \w     86.00 112.00   0.40    1.50    --  107.75  77.00   0.00   65
 25  \w     95.00 130.20   0.40    1.50    --  107.75  61.00 -60.00   88
 26  \w     86.00 112.00   0.40    1.50    --  107.75  77.00 -90.00   65
 27  \w     95.00 132.20   0.40    1.50    --  107.75  61.00-150.00   93
 28  \w     91.00 176.20   0.40    1.50    --  107.75  61.00-180.00  213
 29  \w     85.00 115.00   0.40    1.50    --  107.75  77.00-120.00   75
 30  \w     85.00 120.20   0.40    1.50    --  107.75  77.00-150.00   88
 31  \w     91.00 125.00   0.40    1.50    --  107.75  61.00-120.00   85
 32  \w     85.00 139.00   0.40    1.50    --  107.75  77.00 -60.00  135
 33  \w     95.00 152.20   0.40    1.50    --  107.75  45.00  30.00  143
 34  \w     96.00 160.00   0.40    1.50    --  107.75 125.00 120.00  160
 35  \w     91.00 141.00   0.40    1.50    --  107.75  61.00  60.00  125
 36  \w     85.00 132.20   0.40    1.50    --  107.75  77.00  90.00  118
 37  \w     93.00 173.00   0.40    1.50    --  107.75  61.00  90.00  200
 38  \w     91.00 176.20   0.40    1.50    --  107.75  61.00 -30.00  213
 39  \w     94.00 155.20   0.40    1.50    --  107.75  61.00 120.00  153
 40  \w     85.00 155.00   0.40    1.50    --  107.75  77.00  30.00  175
 41  \w     85.00 115.00   0.40    1.50    --  107.75  77.00 -30.00   75
 42  \w     92.00 166.00   0.40    1.50    --  107.75  61.00   0.00  185
 43  \w     85.00 136.20   0.40    1.50    --  107.75  77.00 120.00  128
 44  \w     85.00 161.00   0.40    1.50    --  107.75  77.00  60.00  190
 45  \w     91.00 134.20   0.40    1.50    --  107.75  61.00 150.00  108
 46  \w     86.00 121.20   0.40    1.50    --  107.75  77.00 150.00   88
 47  \w     51.00  76.20   0.40    0.35    --   74.00  78.00 126.33   63
 48  \w     45.00  70.20   0.40    0.35    --   66.00  72.00 143.61   63
 49  \w     43.00  69.00   0.40    0.35    --   66.00  77.00 105.76   65
 50  \w     44.00  70.00   0.40    0.35    --   66.00  77.00 157.83   65
 51  \w     26.00  50.80   0.40    0.35    --   48.16  77.00 120.00   62
 52  \w     27.00  95.00   0.40    0.35    --   50.00  77.00  77.28  170
 53  \w     68.00  95.20   0.40    1.50    --   90.00  79.00  10.97   68
 54  \w     39.00  75.00   0.40    0.35    --   62.00  77.00   0.90   90
 55  \w     48.00  78.00   0.40    0.35    --   70.00  76.00  56.58   75
 56  \w     48.00  79.20   0.40    0.35    --   70.00  75.00  78.89   78
 57  \w     30.00  56.00   0.40    0.35    --   54.00  79.00 154.75   65
 58  \w    -13.00  14.20   0.40    0.35    --   22.00 102.00  34.79   68
 59  \w     -6.00  29.20   0.40    0.35    --   26.00  96.00 -29.30   88
 60  \w     27.00  59.00   0.40    0.35    --   48.16  77.00 -60.00   80
 61  \w     42.00  67.20   0.40    0.35    --   66.00  79.00 -38.50   63
 62  \w     36.00 124.00   0.40    0.35    --   48.16  19.00-108.00  220
 63  \w     92.00 153.20   0.40    1.50    --  107.75  61.00 -90.00  153
 64  \w     85.00 132.20   0.40    1.50    --  107.75  77.00-180.00  118
 65  \w     40.00  66.00   0.40    0.35    --   62.00  75.00-133.02   65
 66  \w     31.00  59.00   0.40    0.35    --   54.00  77.00 -97.00   70
 67  \w     17.00  43.00   0.40    0.35    --   42.00  83.00-175.74   65
 68  \w     34.00  60.00   0.40    0.35    --   58.00  79.00-161.42   65
 69  \w     15.00  43.00   0.40    0.35    --   42.00  87.00-136.59   70
 70  \w     36.00  71.20   0.40    1.50    --  107.75 -61.00-150.00   88
 71  \w     41.00 105.00   0.40    1.50    --  107.75 -94.00-180.00  160
 72  \w     84.00 111.20   0.40    1.50    --  107.75-125.00-120.00   68
 73  \w     80.00 110.00   0.40    1.50    --  107.75-125.00 -90.00   75
 74  \w     86.00 112.00   0.40    1.50    --  107.75-125.00 -30.00   65
 75  \w     84.00 111.20   0.40    1.50    --  107.75-125.00  30.00   68
 76  \w     81.00 106.20   0.40    1.50    --  107.75 -77.00  60.00   63
 77  \w     68.00 112.00   0.40    1.50    --  107.75-125.00 120.00  110
 78  \w     42.00  73.20   0.40    1.50    --  107.75-125.00  30.00   78
 79  \w     35.00  74.20   0.40    1.50    --  107.75-125.00 -30.00   98
 80  \w     80.00 112.00   0.40    1.50    --  107.75-125.00 -60.00   80
 81  \w     44.00  70.00   0.40    1.50    --  107.75-125.00-120.00   65
 82  \w     35.00  94.20   0.40    1.50    --  107.75 -77.00 -60.00  148
 83  \w     38.00 116.00   0.40    1.50    --  107.75-132.00-153.86  195
 84  \w     34.00  96.00   0.40    0.35    --   48.16-125.00 -30.00  155
 85  \w     36.00  95.20   0.40    0.35    --   48.16-125.00  90.00  148
 86  \w     35.00  64.20   0.40    1.50    --  107.75-125.00 120.00   73
 87  \w     39.00 111.00   0.40    1.50    --  107.75-125.00  90.00  180
 88  \w     39.00  92.20   0.40    1.50    --  107.75 -77.00  90.00  133
 89  \w     36.00  60.80   0.40    1.50    --  107.75 -77.00  60.00   62
 90  \w     36.00  62.00   0.40    1.50    --  107.75 -77.00 120.00   65
 91  \w     36.00 112.00   0.40    1.50    --  107.75-125.00  60.00  190
 92  \w     35.00  74.20   0.40    1.50    --  107.75-125.00 -90.00   98
 93  \w     38.00 114.00   0.40    1.50    --  107.75-131.00-174.84  190
 94  \w     35.00 106.20   0.40    1.50    --  107.75 -77.00-180.00  178
 95  \w     37.00  99.00   0.40    1.50    --  107.75 -77.00 -90.00  155
 96  \w     35.00  59.80   0.40    1.50    --  107.75-125.00 -60.00   62
 97  \w     35.00  68.20   0.40    1.50    --  107.75 -94.00 -90.00   83
 98  \w     35.00  89.00   0.40    1.50    --  107.75 -77.00  30.00  135
 99  \w    -26.00  26.00   0.40    0.35    --   48.16 -19.00  84.00  130
100  \w    -44.00 -16.00   0.40    0.35    --    6.00 130.00  92.52   70
101  \w    -86.00 -12.80   0.40    0.35    --  -48.16 125.00 -60.00  183
102  \w   -123.00 -35.00   0.40    0.35    --  -48.16 -19.00  84.00  220
103  \w    -57.00 -31.00   0.40    0.35    --  -54.00 -78.00-119.27   65
104  \w    -69.00 -43.00   0.40    0.35    --  -66.00 -76.00-146.12   65
105  \w    -77.00 -51.00   0.40    1.50    --  -74.00 -76.00-101.34   65
106  \w    -78.00 -52.00   0.40    1.50    --  -74.00 -75.00-116.93   65
107  \w    -76.00 -50.00   0.40    1.50    --  -74.00 -80.00 -76.74   65
108  \w    -83.00 -57.00   0.40    1.50    --  -78.00 -73.00-155.03   65
109  \w    -87.00 -61.00   0.40    1.50    --  -82.00 -76.00 -92.99   65
110  \w    -88.00 -63.20   0.40    1.50    --  -86.25 -79.00-116.89   62
111  \w    -93.00 -63.00   0.40    1.50    --  -86.00 -76.00-101.70   75
112  \w    -91.00 -65.00   0.40    1.50    --  -86.25 -75.00-111.49   65
113  \w    -97.00 -63.80   0.40    1.50    --  -86.25 -77.00-150.00   83
114  \w   -106.00 -62.00   0.40    1.50    --  -86.25 -80.00-159.21  110
115  \w    -97.00 -63.80   0.40    1.50    --  -86.25 -77.00-180.00   83
116  \w   -119.00 -63.00   0.40    1.50    --  -86.25 -78.00 -66.76  140
117  \w    -94.00 -62.00   0.40    1.50    --  -86.25 -80.00  -6.21   80
118  \w    -79.00 -37.80   0.40    0.35    --  -62.00 -80.00  43.53  103
119  \w    -89.00 -43.00   0.40    0.35    --  -66.00 -78.00  16.02  115
120  \w    -83.00 -57.00   0.40    1.50    --  -78.00 -75.00  89.38   65
121  \w    -78.00 -53.20   0.40    1.50    --  -74.00 -73.00 134.77   62
122  \w    -77.00 -52.20   0.40    1.50    --  -74.00 -76.00 174.07   62
123  \w    -91.00 -57.00   0.40    1.50    --  -78.00 -72.00 126.01   85
124  \w    -84.00 -54.00   0.40    1.50    --  -78.00 -80.00  59.22   75
125  \w    -88.00 -57.20   0.40    1.50    --  -78.00 -73.00  31.06   77
126  \w    -90.00 -64.00   0.40    1.50    --  -86.25 -75.00  82.17   65
127  \w    -92.00 -64.80   0.40    1.50    --  -86.25 -75.00 109.72   68
128  \w    -90.00 -64.00   0.40    1.50    --  -86.00 -74.00 149.05   65
129  \w    -95.00 -69.00   0.40    1.50    --  -86.25 -71.00 162.00   65
130  \w    -91.00 -63.80   0.40    1.50    --  -86.25 -77.00 120.00   68
131  \w    -90.00 -64.00   0.40    1.50    --  -86.25 -75.00  91.57   65
132  \w    -93.00 -64.20   0.40    1.50    --  -86.25 -77.00  30.00   72
133  \w   -107.00 -59.80   0.40    1.50    --  -82.00 -76.00  -7.41  118
134  \w    -97.00 -65.80   0.40    1.50    --  -86.25 -71.00   5.66   78
135  \w    -96.00 -63.20   0.40    1.50    --  -86.25 -79.00 -39.24   82
136  \w   -111.00 -65.80   0.40    1.50    --  -86.25 -70.00  38.63  113
137  \w   -107.00 -65.00   0.40    1.50    --  -86.25 -77.00 -30.00  105
138  \w   -121.00 -65.80   0.40    1.50    --  -86.25 -72.00  64.52  138
139  \w   -133.00 -85.00   0.40    0.35    --  -62.00 -80.00  43.53  120
140  \w   -139.00-113.00   0.40    1.50    --  -78.00 -80.00  59.22   65
141  \w   -162.00 -73.20   0.40    1.50    --  -86.25 -19.00  84.00  222
142  \w   -159.00-101.80   0.40    1.50    --  -86.25 -71.00   5.66  143
143  \w   -121.00 -35.80   0.40    0.35    --  -48.16 -37.00-180.00  213
;
_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      -0.1890123000
_diffrn_orient_matrix_UB_12      0.0564802000
_diffrn_orient_matrix_UB_13      -0.0176720000
_diffrn_orient_matrix_UB_21      0.0719590000
_diffrn_orient_matrix_UB_22      0.0918308000
_diffrn_orient_matrix_UB_23      0.0044137000
_diffrn_orient_matrix_UB_31      0.0542146000
_diffrn_orient_matrix_UB_32      -0.0073465000
_diffrn_orient_matrix_UB_33      -0.0676593000
_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  0.1481
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            91708
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         87.053
_diffrn_reflns_theta_min         3.099
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.742
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80561
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.57a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_description       plate
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         5049
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0936
_refine_ls_R_factor_gt           0.0791
_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^)+(0.1591P)^2^+0.6340P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2417
_refine_ls_wR_factor_ref         0.2643
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4092
_reflns_number_total             5049
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc05119f5.cif
_cod_data_source_block           DI-F-Acphb
_cod_depositor_comments
'Adding full bibliography for 7132564--7132565.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7132565
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_min   0.930
_shelx_estimated_absorpt_t_max   0.993
_oxdiff_exptl_absorpt_empirical_full_min 0.610
_oxdiff_exptl_absorpt_empirical_full_max 2.174
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_oxdiff_digest_frames
;
01e6ccd4f63144fa3e4892ad7d954410f7144805084
;
_diffrn_oxdiff_digest_hkl
;
0153c45d377c1eaae85a04d5b237672fc2f4b2
;
_shelx_res_checksum              6368
_shelx_hkl_checksum              14335