Synthesis of a new fluorophore: wavelength-tunable bisbenzo[<i>f</i>]isoindolylidenes.
Ye, Changqing; Huang, Rui; Chiou, Mong-Feng; Wang, Bo; Li, Daliang; Bao, Hongli; Chemical science 14 (2023) 13151–13158; doi:10.1039/d3sc04445a

data_1570240
_publ_section_title
;
 Synthesis of a new fluorophore: wavelength-tunable
 bisbenzo[<i>f</i>]isoindolylidenes.
;
_journal_issue                   45
_journal_name_full               'Chemical science'
_journal_page_first              13151
_journal_page_last               13158
_journal_paper_doi               10.1039/d3sc04445a
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C48 H30 N2'
_chemical_formula_sum            'C48 H30 N2'
_chemical_formula_weight         634.74
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-05-06
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-12-13 deposited with the CCDC.	2023-11-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.720(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.1849(11)
_cell_length_b                   8.0013(4)
_cell_length_c                   21.2949(13)
_cell_measurement_reflns_used    11851
_cell_measurement_temperature    100.01(13)
_cell_measurement_theta_max      60.2440
_cell_measurement_theta_min      2.8410
_cell_volume                     3246.4(3)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_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_environment      N~2~
_diffrn_ambient_temperature      100.01(13)
_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 0.953
_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     20.00  56.00   0.50    0.22    --   72.41-125.00   0.00   72
  2  \w     77.00 108.00   0.50    0.22    --   72.41-125.00   0.00   62
  3  \w     19.00  94.00   0.50    0.22    --   72.41 -95.00  41.00  150
  4  \w     17.00  71.00   0.50    0.22    --   72.41 -38.00  90.00  108
  5  \w     88.00 132.00   0.50    0.22    --   72.41  95.00 150.00   88
  6  \w    -33.00  17.00   0.50    0.06    --   -1.25  95.00 150.00  100
  7  \w    -94.00 -33.00   0.50    0.22    --  -74.91  95.00 150.00  122
  8  \w    -56.00  -1.00   0.50    0.22    --  -74.91  38.00 150.00  110
  9  \w     46.00  71.00   0.50    0.06    --   -1.25  57.00 -90.00   50
 10  \w    -68.00  11.00   0.50    0.06    --   -1.25 -57.00   0.00  158
 11  \w   -131.00 -83.00   0.50    0.22    --  -74.91-125.00 -60.00   96
 12  \w   -142.00-106.00   0.50    0.22    --  -74.91-125.00 -30.00   72
 13  \w   -137.00-107.00   0.50    0.22    --  -74.91 -99.00 -30.00   60
 14  \w   -146.00-101.00   0.50    0.22    --  -74.91 -95.00  41.00   90
 15  \w   -146.00 -90.00   0.50    0.22    --  -74.91 -99.00  90.00  112
 16  \w   -147.00 -88.00   0.50    0.22    --  -74.91 -99.00 120.00  118
 17  \w    -22.00   3.00   0.50    0.06    --   -1.25 -95.00  41.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0486861000
_diffrn_orient_matrix_UB_12      0.0170125000
_diffrn_orient_matrix_UB_13      -0.0499610000
_diffrn_orient_matrix_UB_21      -0.0225750000
_diffrn_orient_matrix_UB_22      -0.1557455000
_diffrn_orient_matrix_UB_23      0.0089921000
_diffrn_orient_matrix_UB_31      -0.0452423000
_diffrn_orient_matrix_UB_32      0.0594362000
_diffrn_orient_matrix_UB_33      0.0378348000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Ga K\a'
_diffrn_radiation_wavelength     1.3405
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_av_unetI/netI     0.0403
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            24902
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        53.543
_diffrn_reflns_theta_max         61.081
_diffrn_reflns_theta_min         2.868
_diffrn_source                   'micro-focus metaljet'
_exptl_absorpt_coefficient_mu    0.367
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72030
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_description       block
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.025
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.415
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     451
_refine_ls_number_reflns         7219
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0778
_refine_ls_R_factor_gt           0.0557
_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^)+(0.0520P)^2^+3.7652P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1406
_refine_ls_wR_factor_ref         0.1627
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5483
_reflns_number_total             7219
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc04445a2.cif
_cod_data_source_block           ycq-ph_auto
_cod_depositor_comments
'Adding full bibliography for 1570237--1570240.cif.'
_cod_database_code               1570240
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CNH
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     56.82
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00F(H00F), C00K(H00K), C00N(H00N), C00O(H00O), C00P(H00P), C00Q(H00Q),
 C00R(H00R), C00S(H00S), C00T(H00T), C00U(H00U), C00V(H00V), C00W(H00W),
 C00X(H00X), C00Y(H00Y), C00Z(H00Z), C010(H010), C011(H011), C012(H012),
 C013(H013), C014(H014), C015(H015), C016(H016), C017(H017), C018(H018),
 C019(H019), C01A(H01A), C01B(H01B), C01C(H01C), C01D(H01D), C01E(H01E)
;
_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 1.796
_oxdiff_exptl_absorpt_empirical_full_min 0.613