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_1551381
_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         'C20 H19 N3, C3 H6'
_chemical_formula_sum            'C23 H25 N3'
_chemical_formula_weight         343.46
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yac'
_space_group_name_H-M_alt        'P 1 2/n 1'
_symmetry_space_group_name_Hall  '-P 2yac'
_symmetry_space_group_name_H-M   'P 1 2/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2018-03-15
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-11-23 deposited with the CCDC.    2019-06-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.247(16)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.6842(19)
_cell_length_b                   15.222(4)
_cell_length_c                   15.865(2)
_cell_measurement_reflns_used    816
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      70.6450
_cell_measurement_theta_min      5.5510
_cell_volume                     1850.6(7)
_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)'
_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 0.989
_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    -66.00  31.00   1.00    3.00    --  -40.48  57.00-120.00   97
  2  \w    -63.00  34.00   1.00    3.00    --  -40.48  38.00  30.00   97
  3  \w      7.00  35.00   1.00    3.00    --   40.48 -99.00 -60.00   28
  4  \w     58.00  93.00   1.00    3.00    --   40.48-125.00  30.00   35
  5  \w     59.00 140.00   1.00    5.00    --  106.95 -77.00 120.00   81
  6  \w     91.00 119.00   1.00    5.00    --  106.95 -45.00 150.00   28
  7  \w     65.00 124.00   1.00    5.00    --  106.95 -45.00  30.00   59
  8  \w     90.00 118.00   1.00    5.00    --  106.95-125.00-120.00   28
  9  \w     35.00 103.00   1.00    5.00    --  106.95 -45.00 -30.00   68
 10  \w     55.00 173.00   1.00    5.00    --  106.95  15.00-120.00  118
 11  \w     78.00 161.00   1.00    5.00    --  106.95  61.00  90.00   83
 12  \w    107.00 175.00   1.00    5.00    --  106.95  77.00 120.00   68
 13  \w     44.00 109.00   1.00    5.00    --  106.95 -95.00  60.00   65
 14  \w     34.00  77.00   1.00    5.00    --  106.95 -45.00 150.00   43
 15  \w     31.00 106.00   1.00    5.00    --  106.95 -95.00 -30.00   75
 16  \w     42.00  67.00   1.00    5.00    --  106.95-125.00-120.00   25
 17  \w     34.00 110.00   1.00    5.00    --  106.95-125.00 -30.00   76
 18  \w   -111.00 -74.00   1.00    3.00    --  -40.48 -57.00  90.00   37
;
_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      0.1219550000
_diffrn_orient_matrix_UB_12      -0.0772961000
_diffrn_orient_matrix_UB_13      0.0255715000
_diffrn_orient_matrix_UB_21      -0.1370871000
_diffrn_orient_matrix_UB_22      -0.0649991000
_diffrn_orient_matrix_UB_23      -0.0390394000
_diffrn_orient_matrix_UB_31      0.0821543000
_diffrn_orient_matrix_UB_32      0.0066185000
_diffrn_orient_matrix_UB_33      -0.0854591000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0964
_diffrn_reflns_av_unetI/netI     0.1702
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11307
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.693
_diffrn_reflns_theta_min         2.903
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.563
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.32830
_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    1.233
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.603
_refine_diff_density_min         -0.391
_refine_diff_density_rms         0.086
_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     236
_refine_ls_number_reflns         3629
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.227
_refine_ls_R_factor_all          0.2253
_refine_ls_R_factor_gt           0.0795
_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^)+(0.1465P)^2^+4.4395P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4114
_refine_ls_wR_factor_ref         0.1468
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1785
_reflns_number_total             3629
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc01035a2.cif
_cod_data_source_block           exp1295
_cod_database_code               1551381
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.941
_shelx_estimated_absorpt_t_min   0.930
_reflns_odcompleteness_completeness 98.61
_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 C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C17(H17A,H17B), C19(H19A,H19B), C21(H21A,H21B), C23(H23A,
 H23B), C22(H22A,H22B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C12(H12), C5(H5), C16(H16), C4(H4), C2(H2), C3(H3), C14(H14),
 C15(H15), C13(H13)
2.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_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 2.084
_oxdiff_exptl_absorpt_empirical_full_min 0.223