Facile synthesis of AIEgens with wide color tunability for cellular imaging and therapy
Xu, Wenhan; Lee, Michelle M. S.; Zhang, Zhihan; Sung, Herman H-Y.; Williams, Ian Duncan; Kwok, Ryan T. K.; Lam, Jacky Wing Yip; Wang, Dong; Tang, Ben Zhong; Chemical Science  (2019) –; doi:10.1039/C8SC05805A

data_1550644
_publ_section_title
;
 Facile synthesis of AIEgens with wide color tunability for cellular
 imaging and therapy
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/C8SC05805A
_journal_year                    2019
_chemical_formula_moiety         'C25 H21 N O3 S'
_chemical_formula_sum            'C25 H21 N O3 S'
_chemical_formula_weight         415.49
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-01-30
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-12-22 deposited with the CCDC.    2019-02-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.5934(19)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.89163(18)
_cell_length_b                   19.5816(3)
_cell_length_c                   10.94012(19)
_cell_measurement_reflns_used    6303
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      74.0830
_cell_measurement_theta_min      4.5180
_cell_volume                     2019.92(6)
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3577
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_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     80.00 174.00   1.00    5.00    --  107.97  30.00  90.00   94
  2  \w    -67.00  28.00   1.00    2.00    --  -40.45  37.00  90.00   95
  3  \w    -96.00  -3.00   1.00    2.00    --  -40.45 125.00 150.00   93
  4  \w   -113.00 -16.00   1.00    2.00    --  -40.45 -37.00 -90.00   97
  5  \w     54.00 108.00   1.00    5.00    --  107.97 -94.00 150.00   54
  6  \w     50.00 136.00   1.00    5.00    --  107.97 -45.00 120.00   86
  7  \w     44.00 131.00   1.00    5.00    --  107.97 -45.00  30.00   87
  8  \w     40.00 132.00   1.00    5.00    --  107.97 -61.00 -90.00   92
  9  \w     79.00 169.00   1.00    5.00    --  107.97 -15.00-150.00   90
 10  \w     38.00 116.00   1.00    5.00    --  107.97-111.00 -60.00   78
 11  \w     25.00 105.00   1.00    5.00    --  107.97 -94.00  60.00   80
 12  \w     25.00  51.00   1.00    5.00    --  107.97 -94.00 150.00   26
;
_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      0.1396902000
_diffrn_orient_matrix_UB_12      0.0181188000
_diffrn_orient_matrix_UB_13      0.1038329000
_diffrn_orient_matrix_UB_21      0.0445906000
_diffrn_orient_matrix_UB_22      -0.0756606000
_diffrn_orient_matrix_UB_23      0.0086556000
_diffrn_orient_matrix_UB_31      0.0722740000
_diffrn_orient_matrix_UB_32      0.0117408000
_diffrn_orient_matrix_UB_33      -0.1046688000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11028
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         67.471
_diffrn_reflns_theta_min         4.516
_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    1.647
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94429
_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    1.366
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     390
_refine_ls_number_reflns         3611
_refine_ls_number_restraints     240
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0325
_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^)+(0.0580P)^2^+0.3490P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0886
_refine_ls_wR_factor_ref         0.0919
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3241
_reflns_number_total             3611
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8sc05805a2.cif
_cod_data_source_block           dw20a
_cod_database_code               1550644
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.46
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C11-C12 \\sim C16-C11 \\sim C15-C16 \\sim C15-C14 \\sim C13-C14 \\sim C12-C13
 with sigma of 0.02
 C11A-C12A \\sim C16A-C11A \\sim C15A-C16A \\sim C15A-C14A \\sim C12A-C13A
\\sim C13A-C14A
 with sigma of 0.02
 S1-C4 \\sim S1-C1 \\sim S1A-C1A \\sim S1A-C4A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(O1A) \\sim Ueq, Uanis(O1) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.002
4. Rigid body (RIGU) restrains
 S1, C2, C15, C14, C13, C1, C11, C16, O1, C12, C4, C3, C5
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 S1A, C2A, C1A, C4A, C3A, O1A, C5A, C11A, C12A, C15A, C16A, C14A, C13A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Others
 Fixed Sof: S1(0.7) S1A(0.3) O1(0.7) O1A(0.3) C1(0.7) C2(0.7) H2(0.7) C3(0.7)
 H3(0.7) C4(0.7) C5(0.7) H5(0.7) C11(0.7) C12(0.7) H12(0.7) C13(0.7) H13(0.7)
 C14(0.7) C15(0.7) H15(0.7) C16(0.7) H16(0.7) C1A(0.3) C2A(0.3) H2A(0.3)
 C3A(0.3) H3A(0.3) C4A(0.3) C5A(0.3) H5A(0.3) C11A(0.3) C12A(0.3) H12A(0.3)
 C13A(0.3) H13A(0.3) C14A(0.3) C15A(0.3) H15A(0.3) C16A(0.3) H16A(0.3)
6.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C12(H12), C13(H13), C15(H15), C16(H16), C2A(H2A),
 C3A(H3A), C5A(H5A), C12A(H12A), C13A(H13A), C15A(H15A), C16A(H16A), C22(H22),
 C23(H23), C25(H25), C26(H26), C32(H32), C33(H33), C35(H35), C36(H36)
6.b Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C30(H30A,H30B,H30C)
;
_olex2_date_sample_data_collection 2017-12-20
_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 1.122
_oxdiff_exptl_absorpt_empirical_full_min 0.884