Assembly of 1H-Isoindole Derivatives by Selective Carbon-Nitrogen Triple Bond Activation: Access to Aggregation-Induced Emission Fluorophores for Lipid Droplets Imaging
Jiang, Huanfeng; He, Dandan; Zhuang, Zeyan; Wang, Xu; Li, Jiawei; Li, Jianxiao; Wu, Wanqing; Zhao, Zujin; Tang, Ben Zhong; Chemical Science  (2019) –; doi:10.1039/C9SC01035A

data_1551380
_publ_section_title
;
 Assembly of 1H-Isoindole Derivatives by Selective Carbon-Nitrogen Triple
 Bond Activation: Access to Aggregation-Induced Emission Fluorophores for
 Lipid Droplets Imaging
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/C9SC01035A
_journal_year                    2019
_chemical_formula_moiety         'C24 H20 F N3 S'
_chemical_formula_sum            'C24 H20 F N3 S'
_chemical_formula_weight         401.49
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-10-26
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-09-26 deposited with the CCDC.    2019-06-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.2070(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.52460(10)
_cell_length_b                   15.58000(10)
_cell_length_c                   9.81710(10)
_cell_measurement_reflns_used    8603
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.5020
_cell_measurement_theta_min      5.3630
_cell_volume                     2035.86(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.984
_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     -7.00  20.00   1.00    1.00    --  -41.11  37.00  30.00   27
  2  \w      1.00  42.00   1.00    1.00    --   41.11 -99.00  90.00   41
  3  \w     36.00 115.00   1.00    1.00    --  106.95 -15.00 120.00   79
  4  \w    111.00 140.00   1.00    1.00    --  106.95 -77.00 120.00   29
  5  \w     64.00 109.00   1.00    1.00    --  106.95 -94.00  60.00   45
  6  \w     62.00  89.00   1.00    1.00    --  106.95 -77.00 120.00   27
  7  \w     35.00 123.00   1.00    1.00    --  106.95 -61.00  90.00   88
  8  \w     87.00 178.00   1.00    1.00    --  106.95  45.00 150.00   91
  9  \w    114.00 171.00   1.00    1.00    --  106.95  45.00  90.00   57
 10  \w    108.00 162.00   1.00    1.00    --  106.95 125.00  90.00   54
 11  \w     98.00 174.00   1.00    1.00    --  106.95  77.00  30.00   76
 12  \w     70.00  97.00   1.00    1.00    --  106.95 -94.00-180.00   27
 13  \w     41.00 120.00   1.00    1.00    --  106.95-125.00 -30.00   79
 14  \w     48.00 132.00   1.00    1.00    --  106.95 -45.00 -30.00   84
 15  \w     39.00  99.00   1.00    1.00    --  106.95 -94.00   0.00   60
 16  \w    -96.00  -7.00   1.00    1.00    --  -41.11 125.00  90.00   89
 17  \w   -116.00 -29.00   1.00    1.00    --  -41.11 -37.00-150.00   87
 18  \w   -108.00 -10.00   1.00    1.00    --  -41.11 -77.00 -30.00   98
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0419505000
_diffrn_orient_matrix_UB_12      -0.0858089000
_diffrn_orient_matrix_UB_13      -0.0634682000
_diffrn_orient_matrix_UB_21      0.1056119000
_diffrn_orient_matrix_UB_22      -0.0255122000
_diffrn_orient_matrix_UB_23      -0.0240282000
_diffrn_orient_matrix_UB_31      0.0217649000
_diffrn_orient_matrix_UB_32      -0.0420462000
_diffrn_orient_matrix_UB_33      0.1442930000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0547
_diffrn_reflns_av_unetI/netI     0.0425
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            13713
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.578
_diffrn_reflns_theta_min         4.369
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.603
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41301
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.555
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         4043
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0490
_refine_ls_R_factor_gt           0.0464
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0847P)^2^+0.3957P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1267
_refine_ls_wR_factor_ref         0.1316
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3710
_reflns_number_total             4043
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc01035a2.cif
_cod_data_source_block           exp_926
_cod_database_code               1551380
_shelx_shelxl_version_number     2017/1
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C11(H11), C3(H3), C12(H12), C6(H6), C5(H5), C4(H4), C19(H19),
 C16(H16), C15(H15), C18(H18)
2.b Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C)
;
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.001
_oxdiff_exptl_absorpt_empirical_full_min 0.511