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_1551378
_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_absolute_configuration ad
_chemical_formula_moiety         'C20 H19 N3'
_chemical_formula_sum            'C20 H19 N3'
_chemical_formula_weight         301.38
_space_group_crystal_system      orthorhombic
_space_group_IT_number           20
_space_group_name_Hall           'C 2c 2'
_space_group_name_H-M_alt        'C 2 2 21'
_symmetry_space_group_name_Hall  'C 2c 2'
_symmetry_space_group_name_H-M   'C 2 2 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2017-06-05
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2018-09-21 deposited with the CCDC.    2019-06-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.32208(15)
_cell_length_b                   18.4404(4)
_cell_length_c                   23.9475(4)
_cell_measurement_reflns_used    3270
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.2140
_cell_measurement_theta_min      4.7770
_cell_volume                     3233.44(11)
_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 2014/5 (Sheldrick, 2014)'
_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 0.999
_diffrn_measured_fraction_theta_max 0.967
_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      1.00  41.00   1.00    1.69    --   40.71 -99.00  30.00   40
  2  \w     24.00  74.00   1.00    1.69    --   40.71-125.00   0.00   50
  3  \w     64.00  99.00   1.00    6.77    --  107.48 -94.00 -60.00   35
  4  \w     52.00 130.00   1.00    6.77    --  107.48 -45.00   0.00   78
  5  \w     83.00 158.00   1.00    6.77    --  107.48  30.00  60.00   75
  6  \w     37.00 104.00   1.00    6.77    --  107.48 -94.00-180.00   67
  7  \w    113.00 140.00   1.00    6.77    --  107.48 111.00-180.00   27
  8  \w   -116.00 -41.00   1.00    1.69    --  -40.71 -37.00 150.00   75
;
_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      0.0390049000
_diffrn_orient_matrix_UB_12      -0.0458451000
_diffrn_orient_matrix_UB_13      0.0524406000
_diffrn_orient_matrix_UB_21      0.1068613000
_diffrn_orient_matrix_UB_22      0.0637973000
_diffrn_orient_matrix_UB_23      0.0256297000
_diffrn_orient_matrix_UB_31      -0.1770039000
_diffrn_orient_matrix_UB_32      0.0284213000
_diffrn_orient_matrix_UB_33      0.0270400000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0150
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            4173
_diffrn_reflns_point_group_measured_fraction_full 0.899
_diffrn_reflns_point_group_measured_fraction_max 0.855
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.543
_diffrn_reflns_theta_min         3.692
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.576
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84605
_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            yellow
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_description       block
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 964 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2798
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0305
_refine_ls_R_factor_gt           0.0299
_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^)+(0.0478P)^2^+0.9289P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0783
_refine_ls_wR_factor_ref         0.0790
_reflns_Friedel_coverage         0.559
_reflns_Friedel_fraction_full    0.766
_reflns_Friedel_fraction_max     0.709
_reflns_number_gt                2742
_reflns_number_total             2798
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc01035a2.cif
_cod_data_source_block           exp_611
_cod_database_code               1551378
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.939
_shelx_estimated_absorpt_t_min   0.893
_reflns_odcompleteness_completeness 99.94
_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:
 N2(H2), C1(H1), C13(H13), C2(H2A), C4(H4), C15(H15), C11(H11), C12(H12),
 C3(H3), C14(H14)
2.b Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C20(H20A,H20B,H20C), C19(H19A,H19B,H19C)
;
_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 1.258
_oxdiff_exptl_absorpt_empirical_full_min 0.595