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_1570237
_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         '0.5(C40 H30 N2)'
_chemical_formula_sum            'C20 H15 N'
_chemical_formula_weight         269.349
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_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                91.733(4)
_cell_angle_beta                 97.302(5)
_cell_angle_gamma                97.178(5)
_cell_formula_units_Z            4
_cell_length_a                   8.9783(6)
_cell_length_b                   11.2080(6)
_cell_length_c                   15.2381(6)
_cell_measurement_reflns_used    6378
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      52.0130
_cell_measurement_theta_min      3.4010
_cell_volume                     1507.38(14)
_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  'olex2.refine 1.3 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.9803
_diffrn_measured_fraction_theta_max 0.9803
_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     41.00  76.00   0.50    0.80    --   55.66  38.00   0.00   70
  2  \w     84.00 110.00   0.50    0.80    --   55.66  38.00   0.00   52
  3  \w     79.00 122.00   0.50    0.80    --   55.66 125.00  90.00   86
  4  \w     84.00 129.00   0.50    0.80    --   55.66 125.00 -60.00   90
  5  \w     45.00 126.00   0.50    0.80    --   55.66  38.00-120.00  162
  6  \w    -15.00  29.00   0.50    0.80    --   55.66 -77.00 -90.00   88
  7  \w     44.00  79.00   0.50    0.80    --   55.66 -77.00 -90.00   70
  8  \w     45.00  70.00   0.50    0.80    --   55.66 -57.00  60.00   50
  9  \w    -13.00  18.00   0.50    0.80    --   55.66 -57.00  60.00   62
 10  \w     18.00  44.00   0.50    0.20    --   -0.78  38.00-180.00   52
 11  \w     32.00  65.00   0.50    0.20    --   -0.78  77.00 -90.00   66
 12  \w    -16.00  11.00   0.50    0.20    --   -0.78  77.00 -90.00   54
 13  \w    -66.00  15.00   0.50    0.80    --  -57.22  57.00 -90.00  162
 14  \w     32.00  90.00   0.50    0.80    --   55.66-125.00 -90.00  116
 15  \w     63.00  89.00   0.50    0.80    --   55.66-101.00 -69.00   52
 16  \w    -89.00 -48.00   0.50    0.80    --  -57.22 -57.00 -30.00   82
 17  \w   -127.00 -88.00   0.50    0.80    --  -57.22-125.00-120.00   78
 18  \w   -128.00 -95.00   0.50    0.80    --  -57.22-125.00  30.00   66
 19  \w   -129.00 -38.00   0.50    0.80    --  -57.22 -77.00 150.00  182
 20  \w   -106.00 -20.00   0.50    0.80    --  -57.22 125.00  30.00  172
 21  \w    -93.00   2.00   0.50    0.80    --  -57.22 101.00  34.00  190
;
_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      0.0575629000
_diffrn_orient_matrix_UB_12      -0.0295790000
_diffrn_orient_matrix_UB_13      0.0806531000
_diffrn_orient_matrix_UB_21      -0.0321235000
_diffrn_orient_matrix_UB_22      -0.1168539000
_diffrn_orient_matrix_UB_23      -0.0252512000
_diffrn_orient_matrix_UB_31      0.1365897000
_diffrn_orient_matrix_UB_32      0.0023741000
_diffrn_orient_matrix_UB_33      -0.0269310000
_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     0.0441
_diffrn_reflns_Laue_measured_fraction_full 0.9803
_diffrn_reflns_Laue_measured_fraction_max 0.9803
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13849
_diffrn_reflns_point_group_measured_fraction_full 0.9803
_diffrn_reflns_point_group_measured_fraction_max 0.9803
_diffrn_reflns_theta_full        51.9312
_diffrn_reflns_theta_max         51.93
_diffrn_reflns_theta_min         2.54
_diffrn_source                   'micro-focus metaljet'
_exptl_absorpt_coefficient_mu    0.335
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84861
_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 yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.187
_exptl_crystal_description       block
_exptl_crystal_F_000             569.104
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.2835
_refine_diff_density_min         -0.3502
_refine_diff_density_rms         0.0625
_refine_ls_d_res_high            0.8514
_refine_ls_d_res_low             15.0979
_refine_ls_goodness_of_fit_ref   1.0116
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    52
_refine_ls_number_parameters     383
_refine_ls_number_reflns         5021
_refine_ls_number_restraints     66
_refine_ls_restrained_S_all      1.0045
_refine_ls_R_factor_all          0.0765
_refine_ls_R_factor_gt           0.0562
_refine_ls_shift/su_max          0.0002
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1161P)^2^+0.0763P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1562
_refine_ls_wR_factor_ref         0.1754
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              13
_reflns_limit_k_min              -13
_reflns_limit_l_max              17
_reflns_limit_l_min              0
_reflns_number_gt                3607
_reflns_number_total             5021
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d3sc04445a2.cif
_cod_data_source_block           YCQ-2(YELLOW)_auto
_cod_depositor_comments
'Adding full bibliography for 1570237--1570240.cif.'
_cod_database_code               1570237
_reflns_odcompleteness_completeness 81.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     56.82
_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. Rigid body (RIGU) restrains
 C00R, C00X, C00Y, C00W, C00H, C00E, C00C, C00F, C009, C005, C008
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00F(H00F), C00G(H00G), C00L(H00L), C00P(H00P), C00Q(H00Q),
 C00R(H00R), C00S(H00S), C00T(H00T), C00U(H00U), C00V(H00V), C00W(H00W),
 C00X(H00X), C00Y(H00Y), C00Z(H00Z), C010(H010), C015(H015), C016(H016)
3.b Idealised Me refined as rotating group:
 C011(H01a,H01b,H01c), C012(H01g,H01h,H01i), C013(H01d,H01e,H01f), C014(H01j,
 H01k,H01l)
;
_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 2.950
_oxdiff_exptl_absorpt_empirical_full_min 0.406