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_1570238
_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         'C19 H13 N S'
_chemical_formula_sum            'C19 H13 N S'
_chemical_formula_weight         287.36
_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                 92.734(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.8893(9)
_cell_length_b                   6.3212(5)
_cell_length_c                   18.6664(15)
_cell_measurement_reflns_used    9516
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      60.3760
_cell_measurement_theta_min      3.6820
_cell_volume                     1401.27(19)
_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_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 1.000
_diffrn_measured_fraction_theta_max 0.983
_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     59.00 147.00   0.50    0.24    --   73.50  57.00-150.00  176
  2  \w     76.00 147.00   0.50    0.24    --   73.50  57.00-180.00  142
  3  \w     79.00 129.00   0.50    0.24    --   73.50 125.00  60.00  100
  4  \w    118.00 147.00   0.50    0.24    --   73.50 125.00 120.00   58
  5  \w     95.00 121.00   0.50    0.24    --   73.50  93.00  42.00   52
  6  \w    -31.00  12.00   0.50    0.06    --   -0.70  93.00  42.00   86
  7  \w    -53.00  -2.00   0.50    0.24    --  -74.91  93.00  42.00  102
  8  \w    -87.00 -61.00   0.50    0.24    --  -74.91  93.00  42.00   52
  9  \w   -102.00 -30.00   0.50    0.24    --  -74.91 125.00-180.00  144
 10  \w     15.00  65.00   0.50    0.06    --   -0.70  38.00-150.00  100
 11  \w    -65.00  -1.00   0.50    0.24    --  -74.91  38.00   0.00  128
 12  \w    -61.00 -34.00   0.50    0.24    --  -74.91  38.00  30.00   54
 13  \w    -89.00  -8.00   0.50    0.24    --  -74.91  57.00 150.00  162
 14  \w     14.00  69.00   0.50    0.06    --   -0.70  77.00  90.00  110
 15  \w   -147.00-112.00   0.50    0.24    --  -74.91 -99.00  30.00   70
 16  \w   -140.00-115.00   0.50    0.24    --  -74.91 -93.00 -69.00   50
 17  \w   -127.00-101.00   0.50    0.24    --  -74.91 -99.00-120.00   52
 18  \w    -26.00  30.00   0.50    0.06    --   -0.70 -93.00 -69.00  112
 19  \w     20.00 105.00   0.50    0.24    --   73.50-125.00  60.00  170
 20  \w     67.00  96.00   0.50    0.24    --   73.50 -99.00 120.00   58
 21  \w     57.00 110.00   0.50    0.24    --   73.50-125.00 150.00  106
 22  \w      1.00  30.00   0.50    0.24    --   73.50 -99.00 120.00   58
 23  \w      2.00  69.00   0.50    0.24    --   73.50 -38.00  90.00  134
 24  \w     25.00  96.00   0.50    0.24    --   73.50-125.00 -60.00  142
 25  \w     64.00  91.00   0.50    0.24    --   73.50 -93.00 -69.00   54
 26  \w     15.00  41.00   0.50    0.24    --   73.50 -93.00 -69.00   52
;
_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      -0.0426489000
_diffrn_orient_matrix_UB_12      -0.0223171000
_diffrn_orient_matrix_UB_13      0.0646448000
_diffrn_orient_matrix_UB_21      -0.0737162000
_diffrn_orient_matrix_UB_22      0.1556409000
_diffrn_orient_matrix_UB_23      -0.0154947000
_diffrn_orient_matrix_UB_31      -0.0740685000
_diffrn_orient_matrix_UB_32      -0.1417662000
_diffrn_orient_matrix_UB_33      -0.0271794000
_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  0.0362
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            17389
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        53.543
_diffrn_reflns_theta_max         60.782
_diffrn_reflns_theta_min         3.753
_diffrn_source                   'micro-focus metaljet'
_exptl_absorpt_coefficient_mu    1.284
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80068
_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 reddish red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.039
_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     191
_refine_ls_number_reflns         3194
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0415
_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^)+(0.0499P)^2^+0.3110P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1082
_refine_ls_wR_factor_ref         0.1151
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2508
_reflns_number_total             3194
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc04445a2.cif
_cod_data_source_block           ycq-1(red)_auto
_cod_depositor_comments
'Adding full bibliography for 1570237--1570240.cif.'
_cod_database_code               1570238
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.975
_shelx_estimated_absorpt_t_min   0.939
_reflns_odcompleteness_completeness 100.00
_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.a Aromatic/amide H refined with riding coordinates:
 C008(H008), C00B(H00B), C00C(H00C), C00D(H00D), C00F(H00F), C00G(H00G),
 C00H(H00H), C00I(H00I), C00J(H00J), C00K(H00K)
2.b Idealised Me refined as rotating group:
 C00L(H00A,H00E,H00L)
;
_shelx_res_checksum              49668
_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 1.734
_oxdiff_exptl_absorpt_empirical_full_min 0.580