Molecular tuning of the crystallization-induced emission enhancement of diphenyl-dibenzofulvene luminogens.
Abdollahi, Maryam F.; You, Jian; Wang, Tao; Zhao, Yuming; Chemical communications (Cambridge, England) 57 (2021) 484–487; doi:10.1039/d0cc07013k

data_7127551
_publ_section_title
;
 Molecular tuning of the crystallization-induced emission enhancement of
 diphenyl-dibenzofulvene luminogens.
;
_journal_issue                   4
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              484
_journal_page_last               487
_journal_paper_doi               10.1039/d0cc07013k
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C40 H30 O2'
_chemical_formula_sum            'C40 H30 O2'
_chemical_formula_weight         542.64
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-10-07
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-07-17 deposited with the CCDC.	2020-11-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.4850(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.15600(10)
_cell_length_b                   7.12960(10)
_cell_length_c                   28.7875(4)
_cell_measurement_reflns_used    21680
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.5850
_cell_measurement_theta_min      3.0550
_cell_volume                     1467.34(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(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 0.994
_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    -24.00  63.00   0.50    0.22    --   47.70 -57.00-103.00  174
  2  \w     35.00  73.00   0.50    1.00    --  107.75 -57.00-103.00   76
  3  \w     74.00 105.00   0.50    1.00    --  107.75 -94.00 -90.00   62
  4  \w     85.00 111.00   0.50    1.00    --  107.75-125.00-150.00   52
  5  \w     35.00  79.00   0.50    1.00    --  107.75 -61.00 -60.00   88
  6  \w     35.00 106.00   0.50    1.00    --  107.75 -94.00   0.00  142
  7  \w     36.00  61.00   0.50    1.00    --  107.75-125.00  30.00   50
  8  \w     35.00 112.00   0.50    1.00    --  107.75-125.00   0.00  154
  9  \w     35.00  79.00   0.50    1.00    --  107.75 -61.00  30.00   88
 10  \w     35.00 106.00   0.50    1.00    --  107.75 -94.00  30.00  142
 11  \w     94.00 178.00   0.50    1.00    --  107.75  15.00 150.00  168
 12  \w     95.00 178.00   0.50    1.00    --  107.75  45.00  90.00  166
 13  \w     95.00 178.00   0.50    1.00    --  107.75  30.00 -60.00  166
 14  \w     95.00 178.00   0.50    1.00    --  107.75  30.00-180.00  166
 15  \w     95.00 178.00   0.50    1.00    --  107.75  45.00-150.00  166
 16  \w     98.00 125.00   0.50    1.00    --  107.75  61.00-180.00   54
 17  \w     87.00 156.00   0.50    1.00    --  107.75  77.00-180.00  138
 18  \w     95.00 164.00   0.50    1.00    --  107.75  77.00 -60.00  138
 19  \w     93.00 178.00   0.50    1.00    --  107.75  57.00  38.00  170
 20  \w     97.00 148.00   0.50    1.00    --  107.75  77.00 150.00  102
 21  \w     94.00 178.00   0.50    1.00    --  107.75  15.00 120.00  168
 22  \w     92.00 162.00   0.50    1.00    --  107.75  61.00 120.00  140
 23  \w     33.00 120.00   0.50    0.22    --   47.70  57.00  38.00  174
 24  \w     35.00 121.00   0.50    0.22    --   47.70  37.00 150.00  172
 25  \w     35.00 112.00   0.50    1.00    --  107.75-125.00  60.00  154
 26  \w     35.00 112.00   0.50    1.00    --  107.75-125.00 120.00  154
 27  \w     35.00 108.00   0.50    1.00    --  107.75-125.00 -30.00  146
 28  \w     35.00  79.00   0.50    1.00    --  107.75 -61.00-180.00   88
 29  \w     35.00  79.00   0.50    1.00    --  107.75 -61.00-150.00   88
 30  \w     36.00  81.00   0.50    1.00    --  107.75-125.00-150.00   90
 31  \w     36.00 110.00   0.50    1.00    --  107.75-125.00-120.00  148
 32  \w    -16.00  28.00   0.50    0.22    --  -47.70  19.00 150.00   88
 33  \w    -43.00 -14.00   0.50    1.00    --  -86.25  45.00  30.00   58
 34  \w    -43.00 -14.00   0.50    1.00    --  -86.25  45.00 -30.00   58
 35  \w    -59.00  25.00   0.50    0.22    --  -47.70  57.00  38.00  168
 36  \w    -59.00 -14.00   0.50    1.00    --  -86.25  57.00  38.00   90
 37  \w    -43.00 -14.00   0.50    1.00    --  -86.25  45.00-150.00   58
 38  \w   -119.00 -33.00   0.50    0.22    --  -47.70 -57.00-103.00  172
 39  \w   -119.00 -73.00   0.50    0.22    --  -47.70-125.00  30.00   92
 40  \w   -159.00 -63.00   0.50    1.00    --  -86.25 -77.00 150.00  192
 41  \w   -158.00 -73.00   0.50    1.00    --  -86.25 -45.00 120.00  170
 42  \w   -159.00 -63.00   0.50    1.00    --  -86.25 -77.00 120.00  192
 43  \w   -159.00 -71.00   0.50    1.00    --  -86.25 -57.00-103.00  176
 44  \w   -159.00 -63.00   0.50    1.00    --  -86.25 -77.00-180.00  192
 45  \w     35.00  60.00   0.50    1.00    --  107.75 -57.00-103.00   50
 46  \w     87.00 113.00   0.50    1.00    --  107.75  73.00-109.00   52
 47  \w    -40.00 -15.00   0.50    0.22    --    6.00 122.00 135.68   50
 48  \w     -7.00  22.00   0.50    0.22    --   22.00  95.00-118.68   58
 49  \w     -8.00  17.00   0.50    0.22    --   26.00 100.00  -9.06   50
 50  \w      1.00  26.00   0.50    0.22    --   30.00  90.00  34.01   50
 51  \w     14.00  39.00   0.50    0.22    --   42.00  88.00 169.04   50
 52  \w    -53.00 -27.00   0.50    0.22    --  -47.95 -77.00 -90.00   52
 53  \w     25.00  56.00   0.50    0.22    --   47.95  77.00  30.00   62
 54  \w     -2.00  46.00   0.50    0.22    --   47.95 -37.00 120.00   96
 55  \w     25.00  86.00   0.50    0.22    --   47.95  77.00   0.00  122
 56  \w     45.00  72.00   0.50    0.22    --   47.95  19.00  90.00   54
 57  \w     83.00 116.00   0.50    0.22    --   47.95  19.00  90.00   66
 58  \w    -53.00 -27.00   0.50    0.22    --  -50.00 -80.00-164.64   52
 59  \w     33.00  59.00   0.50    0.22    --   54.00  77.00 150.36   52
 60  \w     30.00  57.00   0.50    0.22    --   54.00  79.00  93.15   54
 61  \w    -72.00 -38.00   0.50    0.22    --  -58.00 -73.00 -27.00   68
 62  \w    -62.00 -36.00   0.50    0.22    --  -58.00 -75.00 161.17   52
 63  \w    -61.00 -36.00   0.50    0.22    --  -58.00 -76.00  22.90   50
 64  \w    -66.00 -40.00   0.50    0.22    --  -62.00 -80.00-118.41   52
 65  \w    -66.00 -40.00   0.50    0.22    --  -62.00 -74.00 -94.11   52
 66  \w     38.00  64.00   0.50    0.22    --   62.00  79.00  28.65   52
 67  \w    -73.00 -47.00   0.50    0.22    --  -66.00 -70.00-178.47   52
 68  \w     42.00  67.00   0.50    0.22    --   66.00  79.00  63.85   50
 69  \w    -77.00 -51.00   0.50    1.00    --  -70.00 -68.00 -63.77   52
 70  \w    -77.00 -52.00   0.50    1.00    --  -70.00 -64.00  95.09   50
 71  \w     47.00  72.00   0.50    0.22    --   70.00  77.00 150.69   50
 72  \w    -76.00 -51.00   0.50    1.00    --  -70.00 -67.00 -48.23   50
 73  \w     48.00  74.00   0.50    0.22    --   70.00  76.00 178.10   52
 74  \w     48.00  74.00   0.50    0.22    --   70.00  75.00 100.76   52
 75  \w    -79.00 -53.00   0.50    1.00    --  -74.00 -75.00 -91.31   52
 76  \w    -78.00 -52.00   0.50    1.00    --  -74.00 -75.00-124.96   52
 77  \w    -83.00 -57.00   0.50    1.00    --  -78.00 -75.00  37.24   52
 78  \w    -86.00 -60.00   0.50    1.00    --  -82.00 -74.00-149.18   52
 79  \w    -86.00 -60.00   0.50    1.00    --  -82.00 -75.00 -45.56   52
 80  \w    -86.00 -60.00   0.50    1.00    --  -82.00 -75.00  10.16   52
 81  \w    -92.00 -66.00   0.50    1.00    --  -86.25 -74.00  70.63   52
 82  \w    -89.00 -63.00   0.50    1.00    --  -86.25 -77.00-120.00   52
 83  \w    -92.00 -66.00   0.50    1.00    --  -86.25 -70.00 100.60   52
 84  \w    -94.00 -68.00   0.50    1.00    --  -86.25 -71.00 154.78   52
 85  \w    -88.00 -62.00   0.50    1.00    --  -86.25 -80.00-159.53   52
 86  \w    -88.00 -63.00   0.50    1.00    --  -86.25 -78.00 -65.86   50
 87  \w    -64.00 -38.00   0.50    1.00    --  -86.25  61.00-180.00   52
 88  \w    -91.00 -65.00   0.50    1.00    --  -86.25 -77.00  60.00   52
 89  \w    -88.00 -63.00   0.50    1.00    --  -86.25 -78.00  94.75   50
 90  \w    -89.00 -63.00   0.50    1.00    --  -86.25 -77.00   0.00   52
 91  \w    -90.00 -64.00   0.50    1.00    --  -86.25 -76.00 -21.70   52
 92  \w    -91.00 -65.00   0.50    1.00    --  -86.25 -77.00 -90.00   52
 93  \w    -93.00 -68.00   0.50    1.00    --  -86.25 -71.00  29.21   50
 94  \w     91.00 118.00   0.50    1.00    --  107.75  61.00-150.00   54
 95  \w     53.00 112.00   0.50    1.00    --  107.75-125.00 150.00  118
 96  \w     87.00 125.00   0.50    1.00    --  107.75  77.00 -30.00   76
 97  \w     39.00  64.00   0.50    1.00    --  107.75-125.00 -90.00   50
 98  \w    127.00 153.00   0.50    1.00    --  107.75  77.00  30.00   52
 99  \w     36.00  62.00   0.50    1.00    --  107.75 -94.00  60.00   52
100  \w     86.00 112.00   0.50    1.00    --  107.75  77.00  30.00   52
101  \w    145.00 171.00   0.50    1.00    --  107.75  61.00 -30.00   52
102  \w     79.00 105.00   0.50    1.00    --  107.75 -94.00-120.00   52
103  \w     93.00 119.00   0.50    1.00    --  107.75  61.00  60.00   52
104  \w     86.00 133.00   0.50    1.00    --  107.75  77.00   0.00   94
105  \w     94.00 141.00   0.50    1.00    --  107.75  61.00 -30.00   94
106  \w     37.00  74.00   0.50    1.00    --  107.75 -61.00  90.00   74
107  \w     89.00 115.00   0.50    1.00    --  107.75  77.00  90.00   52
108  \w     86.00 112.00   0.50    1.00    --  107.75  77.00 -60.00   52
109  \w     95.00 152.00   0.50    1.00    --  107.75  77.00-150.00  114
110  \w     91.00 160.00   0.50    1.00    --  107.75  61.00   0.00  138
111  \w     91.00 117.00   0.50    1.00    --  107.75  61.00  90.00   52
112  \w    153.00 178.00   0.50    1.00    --  107.75  61.00-120.00   50
113  \w     91.00 121.00   0.50    1.00    --  107.75  61.00-120.00   60
114  \w    131.00 169.00   0.50    1.00    --  107.75  77.00 -90.00   76
115  \w     85.00 118.00   0.50    1.00    --  107.75  77.00 -90.00   66
116  \w    134.00 168.00   0.50    1.00    --  107.75  61.00 -60.00   68
117  \w     94.00 124.00   0.50    1.00    --  107.75  61.00 -60.00   60
118  \w    124.00 173.00   0.50    1.00    --  107.75  73.00-109.00   98
;
_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      0.0246969000
_diffrn_orient_matrix_UB_12      0.1235570000
_diffrn_orient_matrix_UB_13      -0.0431960000
_diffrn_orient_matrix_UB_21      0.1986323000
_diffrn_orient_matrix_UB_22      -0.0790792000
_diffrn_orient_matrix_UB_23      -0.0047015000
_diffrn_orient_matrix_UB_31      -0.0798243000
_diffrn_orient_matrix_UB_32      -0.1586422000
_diffrn_orient_matrix_UB_33      -0.0313260000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            14159
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.882
_diffrn_reflns_theta_min         3.073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.576
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95137
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.61a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_description       plate
_exptl_crystal_F_000             572
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.074
_exptl_crystal_size_min          0.049
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Flack x determined using 2873 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.27(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     380
_refine_ls_number_reflns         14159
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0517
_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^)+(0.0599P)^2^+1.2039P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1359
_refine_ls_wR_factor_ref         0.1387
_reflns_Friedel_coverage         0.982
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.978
_reflns_number_gt                13401
_reflns_number_total             14159
_reflns_threshold_expression     'I > 2\s(I)'
_twin_special_details
;
Component 2 rotated by -179.9273\% 
 around [-0.70 0.70 0.12] (reciprocal) or [-0.71 0.71 -0.00] (direct)
;
_cod_data_source_file            d0cc07013k2.cif
_cod_data_source_block           mf65_twin_hklf5
_cod_depositor_comments
'Adding full bibliography for 7127545--7127552.cif.'
_cod_database_code               7127551
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C40H30O2
_shelx_estimated_absorpt_t_max   0.972
_shelx_estimated_absorpt_t_min   0.934
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.7330(17)
 0.2670(17)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
3.a Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C34(H34A,H34B)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12),
 C16(H16), C17(H17), C19(H19), C20(H20), C23(H23), C24(H24), C25(H25), C26(H26),
  C27(H27), C29(H29), C30(H30), C32(H32), C33(H33), C36(H36), C37(H37),
 C38(H38), C39(H39), C40(H40)
;
_shelx_res_checksum              81941
_shelx_hkl_checksum              56387
_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 1.392
_oxdiff_exptl_absorpt_empirical_full_min 0.845
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2