Functionalized Acrylonitriles with Aggregation-Induced Emission: Structure Tuning by Simple Reaction-Condition Variation, Efficient Red Emission, and Two-Photon Bioimaging.
Niu, Guangle; Zheng, Xiuli; Zhao, Zheng; Zhang, Haoke; Wang, Jianguo; He, Xuewen; Chen, Yuncong; Shi, Xiujuan; Ma, Chao; Kwok, Ryan T. K.; Lam, Jacky W. Y.; Sung, Herman H. Y.; Williams, Ian D.; Wong, Kam Sing; Wang, Pengfei; Tang, Ben Zhong; Journal of the American Chemical Society 141 (2019) 15111–15120; doi:10.1021/jacs.9b06196

data_4129002
_publ_section_title
;
 Functionalized Acrylonitriles with Aggregation-Induced Emission:
 Structure Tuning by Simple Reaction-Condition Variation, Efficient Red
 Emission, and Two-Photon Bioimaging.
;
_journal_issue                   38
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15111
_journal_page_last               15120
_journal_paper_doi               10.1021/jacs.9b06196
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         'C47 H33 N3 S2'
_chemical_formula_sum            'C47 H33 N3 S2'
_chemical_formula_weight         703.88
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-01-31
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 106.45(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.2363(16)
_cell_length_b                   8.7977(9)
_cell_length_c                   45.590(10)
_cell_measurement_reflns_used    2769
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.7670
_cell_measurement_theta_min      4.7910
_cell_volume                     3552.9(11)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (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 10.3577
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.945
_diffrn_measured_fraction_theta_max 0.943
_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     54.00 174.00   1.00    4.00    --  111.82  15.00 -60.00  120
  2  \w    -70.00  34.00   1.00    2.00    --  -39.95  57.00-150.00  104
  3  \w    -96.00  -2.00   1.00    2.00    --  -39.95 125.00 -90.00   94
  4  \w    121.00 178.00   1.00    4.00    --  111.82 125.00-120.00   57
  5  \w     67.00 131.00   1.00    4.00    --  111.82 -45.00 -30.00   64
  6  \w     64.00 109.00   1.00    4.00    --  111.82 -94.00 -30.00   45
  7  \w     37.00 140.00   1.00    4.00    --  111.82 -30.00 -90.00  103
  8  \w     29.00  54.00   1.00    4.00    --  111.82 -94.00 -30.00   25
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0309820000
_diffrn_orient_matrix_UB_12      0.0835599000
_diffrn_orient_matrix_UB_13      -0.0348317000
_diffrn_orient_matrix_UB_21      0.0143368000
_diffrn_orient_matrix_UB_22      0.1396744000
_diffrn_orient_matrix_UB_23      -0.0533767000
_diffrn_orient_matrix_UB_31      -0.0090455000
_diffrn_orient_matrix_UB_32      -0.0643126000
_diffrn_orient_matrix_UB_33      -0.1618812000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0586
_diffrn_reflns_av_unetI/netI     0.0664
_diffrn_reflns_Laue_measured_fraction_full 0.945
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       54
_diffrn_reflns_limit_l_min       -54
_diffrn_reflns_number            10607
_diffrn_reflns_point_group_measured_fraction_full 0.945
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         67.498
_diffrn_reflns_theta_min         4.044
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Cu
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    1.656
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78804
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (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    1.316
_exptl_crystal_description       plate
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.707
_refine_diff_density_min         -0.498
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     469
_refine_ls_number_reflns         6052
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0821
_refine_ls_R_factor_gt           0.0625
_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^)+(0.0470P)^2^+5.9440P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1336
_refine_ls_wR_factor_ref         0.1430
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4923
_reflns_number_total             6052
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b06196_si_002.cif
_cod_data_source_block           niu10cult
_cod_database_code               4129002
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.922
_shelx_estimated_absorpt_t_min   0.755
_reflns_odcompleteness_completeness 98.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C8(H8), C9(H9), C12(H12), C13(H13), C15(H15),
 C16(H16), C22(H22), C23(H23), C25(H25), C26(H26), C32(H32), C33(H33), C34(H34),
  C35(H35), C36(H36), C42(H42), C43(H43), C44(H44), C45(H45), C46(H46),
 C52(H52), C53(H53), C54(H54), C55(H55), C56(H56), C62(H62), C63(H63), C64(H64),
  C65(H65), C66(H66)
;
_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 1.211
_oxdiff_exptl_absorpt_empirical_full_min 0.845