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_1557087
_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         'C39 H34 N3 O, F6 P'
_chemical_formula_sum            'C39 H34 F6 N3 O P'
_chemical_formula_weight         705.66
_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     iterative
_audit_creation_date             2017-06-30
_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                 102.511(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.3923(3)
_cell_length_b                   29.4208(8)
_cell_length_c                   11.9664(3)
_cell_measurement_reflns_used    4012
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      74.6850
_cell_measurement_theta_min      4.0400
_cell_volume                     3228.14(16)
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_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 0.981
_diffrn_measured_fraction_theta_max 0.941
_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     85.00 176.00   1.00    3.00    --  110.76  45.00-180.00   91
  2  \w    -62.00  33.00   1.00    2.00    --  -41.51  37.00  60.00   95
  3  \w   -115.00 -13.00   1.00    2.00    --  -41.51 -57.00 -90.00  102
  4  \w    106.00 178.00   1.00    3.00    --  110.76 125.00  30.00   72
  5  \w     83.00 178.00   1.00    3.00    --  110.76  30.00  90.00   95
  6  \w     32.00 109.00   1.00    3.00    --  110.76 -94.00 -30.00   77
;
_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      0.1038510000
_diffrn_orient_matrix_UB_12      0.0110673000
_diffrn_orient_matrix_UB_13      -0.0798496000
_diffrn_orient_matrix_UB_21      0.1098073000
_diffrn_orient_matrix_UB_22      0.0208242000
_diffrn_orient_matrix_UB_23      0.1015337000
_diffrn_orient_matrix_UB_31      0.0734229000
_diffrn_orient_matrix_UB_32      -0.0467514000
_diffrn_orient_matrix_UB_33      0.0265425000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10260
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         76.186
_diffrn_reflns_theta_min         4.072
_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    1.390
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76026
_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_density_diffrn    1.452
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1464
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.980
_refine_diff_density_min         -0.515
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     453
_refine_ls_number_reflns         6341
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0750
_refine_ls_R_factor_gt           0.0650
_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^)+(0.0980P)^2^+3.9500P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1706
_refine_ls_wR_factor_ref         0.1803
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5333
_reflns_number_total             6341
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc06441a2.cif
_cod_data_source_block           zhengz10cult
_cod_depositor_comments
;Adding full bibliography for 1557087--1557088.cif.

 Adding full bibliography for 1557087--1557088.cif.
;
_cod_database_code               1557087
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 98.50
_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, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C39(H39A,H39B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11), C13(H13), C14(H14),
 C16(H16), C18(H18), C19(H19), C22(H22), C23(H23), C25(H25), C28(H28), C29(H29),
  C30(H30), C31(H31), C32(H32), C34(H34), C35(H35), C36(H36), C37(H37), C38(H38)
2.c Idealised Me refined as rotating group:
 C40(H40A,H40B,H40C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              13210
_olex2_date_sample_data_collection 2017-06-28
_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 1.248
_oxdiff_exptl_absorpt_empirical_full_min 0.800