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_1570239
_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         'C36 H22 N2'
_chemical_formula_sum            'C36 H22 N2'
_chemical_formula_weight         482.55
_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             2019-11-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-12-13 deposited with the CCDC.	2023-11-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.414(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.4695(8)
_cell_length_b                   5.8013(3)
_cell_length_c                   17.3780(10)
_cell_measurement_reflns_used    2426
_cell_measurement_temperature    299.22(19)
_cell_measurement_theta_max      57.6510
_cell_measurement_theta_min      3.4530
_cell_volume                     1232.25(13)
_computing_cell_refinement       'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      299.22(19)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.964
_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    -71.00 -39.00   0.50    0.60    --   -1.41 -18.00  48.00   64
  2  \w    -34.00  14.00   0.50    0.60    --   -1.41 -18.00  48.00   96
  3  \w      1.00  26.00   0.50    2.40    --   72.34 -18.00  48.00   50
  4  \w      0.00  43.00   0.50    2.40    --   72.34 -38.00  90.00   86
  5  \w      1.00  63.00   0.50    2.40    --   72.34 -57.00-120.00  124
  6  \w     68.00  96.00   0.50    2.40    --   72.34 -77.00-120.00   56
  7  \w     43.00 108.00   0.50    2.40    --   72.34-125.00-120.00  130
  8  \w     17.00  59.00   0.50    2.40    --   72.34 -77.00-120.00   84
  9  \w     57.00 136.00   0.50    2.40    --   72.34  18.00-143.00  158
 10  \w     40.00  70.00   0.50    0.60    --   -1.41  38.00-150.00   60
 11  \w     20.00  45.00   0.50    0.60    --   -1.41  18.00-143.00   50
 12  \w     10.00  35.00   0.50    0.60    --   -1.41  38.00-150.00   50
 13  \w    -26.00  -1.00   0.50    2.40    --  -75.15  18.00-143.00   50
 14  \w    -26.00  -1.00   0.50    2.40    --  -75.15  19.00-180.00   50
 15  \w    -42.00  -5.00   0.50    2.40    --  -75.15  38.00 -30.00   74
 16  \w    -28.00  -2.00   0.50    2.40    --  -75.15  38.00   0.00   52
 17  \w    -66.00  -6.00   0.50    2.40    --  -75.15  57.00   0.00  120
 18  \w   -146.00 -71.00   0.50    2.40    --  -75.15 -18.00  48.00  150
;
_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      -0.0348030000
_diffrn_orient_matrix_UB_12      0.0363363000
_diffrn_orient_matrix_UB_13      -0.0769642000
_diffrn_orient_matrix_UB_21      -0.1031689000
_diffrn_orient_matrix_UB_22      -0.0389979000
_diffrn_orient_matrix_UB_23      0.0078963000
_diffrn_orient_matrix_UB_31      -0.0122712000
_diffrn_orient_matrix_UB_32      0.2246143000
_diffrn_orient_matrix_UB_33      0.0138182000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.3405
_diffrn_reflns_av_R_equivalents  0.0691
_diffrn_reflns_av_unetI/netI     0.0603
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            9039
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        53.543
_diffrn_reflns_theta_max         60.545
_diffrn_reflns_theta_min         3.488
_diffrn_source                   'micro-focus metaljet'
_exptl_absorpt_coefficient_mu    0.375
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52010
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.59a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'dark orange'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_description       needle
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2730
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0937
_refine_ls_R_factor_gt           0.0617
_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^)+(0.1205P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1756
_refine_ls_wR_factor_ref         0.2001
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1785
_reflns_number_total             2730
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc04445a2.cif
_cod_data_source_block           ycq-20191111
_cod_depositor_comments
'Adding full bibliography for 1570237--1570240.cif.'
_cod_database_code               1570239
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         CHN
_diffrn_oxdiff_digest_frames
;
01e5f25597962cb53dc4c9cc56247b967d00030662d
;
_diffrn_oxdiff_digest_hkl
;
01e9d0dd0db28c3d29d169c03e3c7c0009f8b2
;
_reflns_odcompleteness_completeness 99.53
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     56.82
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H009(0.068) H00A(0.066) H00B(0.073) H00C(0.08) H00D(0.078)
 H00E(0.079) H00F(0.084) H00G(0.092) H00H(0.09) H00I(0.098) H00J(0.107)
 Fixed X: H009(0.486267) H00A(0.691839) H00B(0.685318) H00C(0.635799)
 H00D(0.639568) H00E(0.488196) H00F(0.537629) H00G(0.738356) H00H(0.861729)
 H00I(0.792933) H00J(0.889775)
 Fixed Y: H009(1.083192) H00A(0.401316) H00B(0.373499) H00C(0.521899)
 H00D(0.469046) H00E(1.05491) H00F(0.864299) H00G(0.18528) H00H(-0.032764)
 H00I(0.328876) H00J(0.042151)
 Fixed Z: H009(0.33321) H00A(0.374449) H00B(0.230933) H00C(0.108102)
 H00D(0.655223) H00E(0.18985) H00F(0.087388) H00G(0.728876) H00H(0.678811)
 H00I(0.480108) H00J(0.554267)
;
_shelx_res_checksum              14380
_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 2.140
_oxdiff_exptl_absorpt_empirical_full_min 0.377