An acrylate AIE-active dye with a two-photon fluorescent switch for fluorescent nanoparticles by RAFT polymerization: synthesis, molecular structure and application in cell imaging
Huang, Zengfang; Chen, Yali; Wang, Runze; Zhou, Chaoyue; Liu, Xiaobo; Mao, Liucheng; Yuan, Jinying; Tao, Lei; Wei, Yen; RSC Advances 10 (2020) 5704–5711; doi:10.1039/C9RA10430E

data_7239873
_publ_section_title
;
 An acrylate AIE-active dye with a two-photon fluorescent switch for
 fluorescent nanoparticles by RAFT polymerization: synthesis, molecular
 structure and application in cell imaging
;
_journal_issue                   10
_journal_name_full               'RSC Advances'
_journal_page_first              5704
_journal_page_last               5711
_journal_paper_doi               10.1039/C9RA10430E
_journal_volume                  10
_journal_year                    2020
_chemical_formula_moiety         'C39 H29 N O2'
_chemical_formula_sum            'C39 H29 N O2'
_chemical_formula_weight         543.63
_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     direct
_audit_creation_date             2019-03-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-04-15 deposited with the CCDC.	2020-01-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.620(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   29.6191(12)
_cell_length_b                   5.7006(2)
_cell_length_c                   17.6543(6)
_cell_measurement_reflns_used    3496
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.3640
_cell_measurement_theta_min      3.0250
_cell_volume                     2929.81(19)
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.969
_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    -42.00  22.00   1.00    1.00    --  -40.98  38.00 120.00   64
  2  \w    -81.00  39.00   1.00    1.00    --  -40.98  19.00-120.00  120
  3  \w     69.00  94.00   1.00    1.00    --   40.98-125.00-150.00   25
  4  \w     55.00  90.00   1.00    1.00    --   40.98-125.00-180.00   35
  5  \w     95.00 171.00   1.00    1.50    --  106.95  45.00-180.00   76
  6  \w    106.00 133.00   1.00    1.50    --  106.95 114.00   9.00   27
  7  \w    114.00 176.00   1.00    1.50    --  106.95 125.00  60.00   62
  8  \w     61.00 172.00   1.00    1.50    --  106.95  15.00 120.00  111
  9  \w     38.00 133.00   1.00    1.50    --  106.95 -45.00 150.00   95
 10  \w     34.00  61.00   1.00    1.50    --  106.95 -95.00 120.00   27
;
_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      -0.0419027000
_diffrn_orient_matrix_UB_12      -0.0287495000
_diffrn_orient_matrix_UB_13      0.0395037000
_diffrn_orient_matrix_UB_21      0.0309249000
_diffrn_orient_matrix_UB_22      -0.1131039000
_diffrn_orient_matrix_UB_23      0.0702818000
_diffrn_orient_matrix_UB_31      0.0094013000
_diffrn_orient_matrix_UB_32      0.2437039000
_diffrn_orient_matrix_UB_33      0.0372328000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10271
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.465
_diffrn_reflns_theta_min         3.036
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.588
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73003
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_description       block
_exptl_crystal_F_000             1144
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.587
_refine_diff_density_min         -0.540
_refine_diff_density_rms         0.119
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     380
_refine_ls_number_reflns         5699
_refine_ls_number_restraints     14
_refine_ls_restrained_S_all      1.943
_refine_ls_R_factor_all          0.0935
_refine_ls_R_factor_gt           0.0702
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1357
_refine_ls_wR_factor_ref         0.1670
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4479
_reflns_number_total             5699
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ra10430e2.cif
_cod_data_source_block           f1
_cod_depositor_comments          'Adding full bibliography for 7239873.cif.'
_cod_database_code               7239873
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.938
_shelx_estimated_absorpt_t_min   0.922
_reflns_odcompleteness_completeness 99.91
_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
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 O1, C36
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 O1, C33
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
O1 \\sim C36: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004
O1 \\sim C33: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004
4.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C14(H14), C12(H12), C13(H13), C20(H20), C26(H26),
 C16(H16), C19(H19), C25(H25), C18(H18), C17(H17), C27(H27), C35(H35), C8(H8),
 C22(H22), C31(H31), C6(H6), C23(H23), C7(H7), C34(H34), C4(H4), C32(H32),
 C5(H5)
4.b X=CH2 refined with riding coordinates:
 C38(H38A,H38B)
4.c Idealised Me refined as rotating group:
 C39(H39A,H39B,H39C)
;
_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 1.549
_oxdiff_exptl_absorpt_empirical_full_min 0.621