Versatile Strategy To Generate a Rhodamine Triplet State as Mitochondria-Targeting Visible-Light Photosensitizers for Efficient Photodynamic Therapy.
Liu, Chuangjun; Zhou, Lihua; Wei, Fangfang; Li, Ling; Zhao, Shunan; Gong, Ping; Cai, Lintao; Wong, Keith Man-Chung; ACS applied materials & interfaces 11 (2019) 8797–8806; doi:10.1021/acsami.8b20224

data_4514556
_publ_section_title
;
 Versatile Strategy To Generate a Rhodamine Triplet State as
 Mitochondria-Targeting Visible-Light Photosensitizers for Efficient
 Photodynamic Therapy.
;
_journal_issue                   9
_journal_name_full               'ACS applied materials &amp; interfaces'
_journal_page_first              8797
_journal_page_last               8806
_journal_paper_doi               10.1021/acsami.8b20224
_journal_volume                  11
_journal_year                    2019
_chemical_formula_moiety         'C35 H35 Br N4 O4 Re, F6 P'
_chemical_formula_sum            'C35 H35 Br F6 N4 O4 P Re'
_chemical_formula_weight         986.75
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yac'
_space_group_name_H-M_alt        'P 1 2/n 1'
_symmetry_space_group_name_Hall  '-P 2yac'
_symmetry_space_group_name_H-M   'P 1 2/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2018-08-07
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.046(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.661(3)
_cell_length_b                   13.734(2)
_cell_length_c                   16.996(3)
_cell_measurement_reflns_used    9129
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.04
_cell_measurement_theta_min      2.26
_cell_volume                     3889.1(11)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0670
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            116706
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.556
_diffrn_reflns_theta_min         2.264
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.263
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5346
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1510 before and 0.0628 after correction. The Ratio of minimum to maximum transmission is 0.7170. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.685
_exptl_crystal_description       block
_exptl_crystal_F_000             1936
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.17
_refine_diff_density_max         4.053
_refine_diff_density_min         -3.439
_refine_diff_density_rms         0.210
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.133
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     595
_refine_ls_number_reflns         8936
_refine_ls_number_restraints     204
_refine_ls_restrained_S_all      1.127
_refine_ls_R_factor_all          0.1665
_refine_ls_R_factor_gt           0.1221
_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^)+(0.0687P)^2^+99.9851P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2666
_refine_ls_wR_factor_ref         0.2911
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6048
_reflns_number_total             8936
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            am8b20224_si_002.cif
_cod_data_source_block           Rh-bpy-Re
_cod_original_cell_volume        3889.0(10)
_cod_database_code               4514556
_shelxl_version_number           2013-2
_shelx_estimated_absorpt_t_max   0.531
_shelx_estimated_absorpt_t_min   0.468
_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. Uiso/Uaniso restraints and constraints
Uanis(C17) \\sim Ueq, Uanis(C19) \\sim Ueq, Uanis(C23) \\sim Ueq, Uanis(C24)
\\sim Ueq, Uanis(C24') \\sim Ueq, Uanis(C25) \\sim Ueq, Uanis(C25') \\sim Ueq,
Uanis(C26) \\sim Ueq, Uanis(C27) \\sim Ueq, Uanis(C29) \\sim Ueq, Uanis(C26')
\\sim Ueq, Uanis(C27') \\sim Ueq, Uanis(C31') \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
Uanis(N1) \\sim Ueq, Uanis(C33) \\sim Ueq, Uanis(C34) \\sim Ueq, Uanis(O1)
\\sim Ueq, Uanis(C34') \\sim Ueq, Uanis(O2) \\sim Ueq, Uanis(N4) \\sim Ueq,
Uanis(N4') \\sim Ueq, Uanis(C32) \\sim Ueq, Uanis(C32') \\sim Ueq, Uanis(C35)
\\sim Ueq, Uanis(C35') \\sim Ueq, Uanis(O4) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
Uanis(C16) \\sim Ueq, Uanis(C18) \\sim Ueq, Uanis(C28) \\sim Ueq, Uanis(C28')
\\sim Ueq, Uanis(C29') \\sim Ueq, Uanis(C30) \\sim Ueq, Uanis(C30') \\sim Ueq:
with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C23') \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(C18) = Uanis(C20)
Uanis(C20) = Uanis(C19)
Uanis(C16) = Uanis(C17)
3. Others
 Fixed Sof: O4(0.5) O3'(0.5) O3(0.5) O4'(0.5) N4'(0.5) N4(0.5) C32'(0.5)
 H32A(0.5) H32B(0.5) H32C(0.5) C34'(0.5) C35(0.5) C35'(0.5) C24(0.5) H24(0.5)
 C29(0.5) H29(0.5) C31(0.5) H31(0.5) C32(0.5) H32D(0.5) H32E(0.5) H32F(0.5)
 C23(0.5) H23(0.5) C30(0.5) C25(0.5) C28(0.5) H28(0.5) C29'(0.5) H29'(0.5)
 C28'(0.5) H28'(0.5) C27'(0.5) C26'(0.5) H26'(0.5) C30'(0.5) C31'(0.5)
 H31'(0.5) C23'(0.5) H23'(0.5) C25'(0.5) H25'(0.5) C24'(0.5) C26(0.5) H26(0.5)
 C27(0.5) C34(0.5) Br1(0.5) Br1'(0.5)
4.a Riding coordinates:
 C28(H28), C28'(H28')
4.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C20(H20A,H20B), C18(H18A,H18B), C16(H16A,H16B)
4.c Me refined with riding coordinates:
 C32'(H32A,H32B,H32C), C21(H21A,H21B,H21C), C15(H15A,H15B,H15C), C32(H32D,H32E,
 H32F), C19(H19A,H19B,H19C), C17(H17A,H17B,H17C)
4.d Aromatic/amide H refined with riding coordinates:
 C13(H13), C10(H10), C7(H7), C3(H3), C8(H8), C2(H2), C24(H24), C29(H29),
 C31(H31), C23(H23), C29'(H29'), C26'(H26'), C31'(H31'), C23'(H23'), C25'(H25'),
  C26(H26)
;
_shelx_res_checksum              22911
_shelx_hkl_checksum              14412
_olex2_submission_special_instructions 'No special instructions were received'