Highly efficient singlet oxygen generation, two-photon photodynamic therapy and melanoma ablation by rationally designed mitochondria-specific near-infrared AIEgens
Zheng, Zheng; Liu, Haixiang; Zhai, Shaodong; Zhang, Haoke; Shan, Guogang; Kwok, Ryan T. K.; Ma, Chao; Sung, Herman H. Y.; Williams, Ian D.; Lam, Jacky W. Y.; Wong, Kam Sing; Hu, Xianglong; Tang, Ben Zhong; Chemical Science 11 (2020) 2494–2503; doi:10.1039/C9SC06441A

data_1557088
_publ_section_title
;
 Highly efficient singlet oxygen generation, two-photon photodynamic
 therapy and melanoma ablation by rationally designed
 mitochondria-specific near-infrared AIEgens
;
_journal_issue                   9
_journal_name_full               'Chemical Science'
_journal_page_first              2494
_journal_page_last               2503
_journal_paper_doi               10.1039/C9SC06441A
_journal_volume                  11
_journal_year                    2020
_chemical_formula_moiety         'C27 H22 N2 O'
_chemical_formula_sum            'C27 H22 N2 O'
_chemical_formula_weight         390.46
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-05-18
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2019-06-07 deposited with the CCDC.	2020-01-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.3297(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.53897(10)
_cell_length_b                   23.1410(2)
_cell_length_c                   9.57210(10)
_cell_measurement_reflns_used    8335
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      75.5480
_cell_measurement_theta_min      3.8140
_cell_volume                     2017.04(4)
_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 0.984
_diffrn_measured_fraction_theta_max 0.983
_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     36.00 111.00   1.00    3.00    --  110.57 -45.00   0.00   75
  2  \w     39.00  96.00   1.00    2.00    --   40.57-125.00-120.00   57
  3  \w     85.00 177.00   1.00    3.00    --  110.57  45.00 -90.00   92
  4  \w     47.00 115.00   1.00    3.00    --  110.57-111.00  30.00   68
  5  \w     37.00 140.00   1.00    3.00    --  110.57 -30.00-120.00  103
  6  \w     35.00 160.00   1.00    3.00    --  110.57 -15.00  90.00  125
  7  \w     39.00 108.00   1.00    3.00    --  110.57 -94.00 150.00   69
  8  \w     32.00 127.00   1.00    3.00    --  110.57 -77.00-150.00   95
  9  \w    -70.00  33.00   1.00    2.00    --  -40.57  57.00-180.00  103
 10  \w   -111.00 -11.00   1.00    2.00    --  -40.57 -57.00   0.00  100
 11  \w   -117.00 -14.00   1.00    2.00    --  -40.57 -37.00-120.00  103
;
_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      -0.1413772000
_diffrn_orient_matrix_UB_12      0.0075053000
_diffrn_orient_matrix_UB_13      0.0445646000
_diffrn_orient_matrix_UB_21      -0.0324694000
_diffrn_orient_matrix_UB_22      0.0570746000
_diffrn_orient_matrix_UB_23      -0.0865634000
_diffrn_orient_matrix_UB_31      -0.0872369000
_diffrn_orient_matrix_UB_32      -0.0334825000
_diffrn_orient_matrix_UB_33      -0.1374925000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0108
_diffrn_reflns_av_unetI/netI     0.0110
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10527
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         67.485
_diffrn_reflns_theta_min         3.820
_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    0.613
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86709
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3583
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0349
_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^)+(0.0620P)^2^+0.6120P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0958
_refine_ls_wR_factor_ref         0.0967
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3471
_reflns_number_total             3583
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc06441a2.cif
_cod_data_source_block           zhengz1a
_cod_depositor_comments
;Adding full bibliography for 1557087--1557088.cif.

 Adding full bibliography for 1557087--1557088.cif.
;
_cod_database_code               1557088
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.13
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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. Others
 Fixed Sof: O1(0.5) O1A(0.5) H20A(0.5) H20(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C41(H41A,H41B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C8(H8), C9(H9), C11(H11), C20(H20A), C20(H20),
 C22(H22), C23(H23), C24(H24), C25(H25), C26(H26), C32(H32), C33(H33), C34(H34),
  C35(H35), C36(H36)
3.c Idealised Me refined as rotating group:
 C42(H42A,H42B,H42C)
;
_shelx_res_checksum              38293
_olex2_date_sample_data_collection 2017-05-17
_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 0.715