A mitochondria-targeted BODIPY-Ir(III) conjugate as a photoinduced ROS generator for the oxidative destruction of triple-negative breast cancer cells
Qiao, Liping; Liu, Jiangping; Kuang, Shi; Liao, Xinxing; Kou, Junfeng; Ji, Liangnian; Chao, Hui; Dalton Transactions  (2021) –; doi:10.1039/D1DT01460A

data_7707476
_publ_section_title
;
 A mitochondria-targeted BODIPY-Ir(III) conjugate as a photoinduced ROS
 generator for the oxidative destruction of triple-negative breast cancer
 cells
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D1DT01460A
_journal_year                    2021
_chemical_formula_moiety
'2(C60 H45 B F2 Ir N8), 2(Cl), 2.25(H4 O2), 2(C7 H8)'
_chemical_formula_sum            'C134 H109 B2 Cl2 F4 Ir2 N16 O5.5'
_chemical_formula_weight         2584.29
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2019-11-13
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-11-17 deposited with the CCDC.	2021-05-26 downloaded from the CCDC.
;
_cell_angle_alpha                93.911(5)
_cell_angle_beta                 92.383(5)
_cell_angle_gamma                104.711(4)
_cell_formula_units_Z            2
_cell_length_a                   17.6837(15)
_cell_length_b                   18.1876(18)
_cell_length_c                   20.173(2)
_cell_measurement_reflns_used    9233
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      53.230
_cell_measurement_theta_min      2.791
_cell_volume                     6249.1(10)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 0.958
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0947
_diffrn_reflns_av_unetI/netI     0.1771
_diffrn_reflns_Laue_measured_fraction_full 0.958
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            49724
_diffrn_reflns_point_group_measured_fraction_full 0.958
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        25.158
_diffrn_reflns_theta_max         25.158
_diffrn_reflns_theta_min         1.014
_exptl_absorpt_coefficient_mu    2.236
_exptl_absorpt_correction_T_max  0.7504
_exptl_absorpt_correction_T_min  0.5887
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1189 before and 0.0735 after correction.
The Ratio of minimum to maximum transmission is 0.7845.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_description       needle
_exptl_crystal_F_000             2606
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.025
_refine_diff_density_max         1.732
_refine_diff_density_min         -1.526
_refine_diff_density_rms         0.173
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1554
_refine_ls_number_reflns         21462
_refine_ls_number_restraints     150
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.1937
_refine_ls_R_factor_gt           0.0981
_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^)+(0.1058P)^2^+60.1282P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2371
_refine_ls_wR_factor_ref         0.2726
_reflns_Friedel_coverage         0.000
_reflns_number_gt                11979
_reflns_number_total             21462
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1dt01460a2.cif
_cod_data_source_block           b
_cod_original_cell_volume        6249.3(10)
_cod_original_formula_sum        'C134 H109 B2 Cl2 F4 Ir2 N16 O5.50'
_cod_database_code               7707476
_shelx_shelxl_version_number     2014/7
_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, All O(H,H) groups
2. Restrained distances
 C128-C134 \\sim C135_$1-C136_$1
 with sigma of 0.02
 C128-C129 \\sim C128-C133
 with sigma of 0.02
3. Rigid bond restraints
 C94, C99, C98, C97, C96, C95
 with sigma for 1-2 distances of 0.02 and sigma for 1-3 distances of 0.04
 C126, C127
 with sigma for 1-2 distances of 0.04 and sigma for 1-3 distances of 0.08
 C129, C130, C131
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.008
4. Uiso/Uaniso restraints and constraints
C140 \\sim C135 \\sim C136 \\sim C137 \\sim C141 \\sim C138 \\sim C139: within
2A with sigma of 0.008 and sigma for terminal atoms of 0.16
C135 \\sim C136 \\sim C137 \\sim C141 \\sim C138 \\sim C140 \\sim C139: within
2A with sigma of 0.008 and sigma for terminal atoms of 0.016
Uanis(O2) \\sim Ueq, Uanis(O3) \\sim Ueq, Uanis(O4) \\sim Ueq, Uanis(O6) \\sim
Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(O1) \\sim Ueq, Uanis(O7) \\sim Ueq, Uanis(Cl2A) \\sim Ueq: with sigma of
0.008 and sigma for terminal atoms of 0.016
Uanis(C52) \\sim Ueq, Uanis(C129) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C130) \\sim Ueq, Uanis(C134) \\sim Ueq, Uanis(C131) \\sim Ueq,
Uanis(C133) \\sim Ueq, Uanis(C128) \\sim Ueq, Uanis(C132) \\sim Ueq: with sigma
of 0.02 and sigma for terminal atoms of 0.04
5. Others
 Fixed Sof: Cl2A(0.75) O3(0.5) H3A(0.5) H3B(0.5) O4(0.5) H4A(0.5) H4B(0.5)
 O6(0.5) H6A(0.5) H6B(0.5) C128(0.4) H12D(0.4) H12E(0.4) H12F(0.4) C129(0.4)
 H129(0.4) C130(0.4) H130(0.4) C131(0.4) H131(0.4) C132(0.4) H132(0.4)
 C133(0.4) H133(0.4) C134(0.4) C135(0.6) H13A(0.6) H13B(0.6) H13C(0.6)
 C136(0.6) C137(0.6) H137(0.6) C138(0.6) H138(0.6) C139(0.6) H139(0.6)
 C140(0.6) H140(0.6) C141(0.6) H141(0.6) Cl2B(0.25)
6.a Riding coordinates:
 O1(H1A,H1B), O2(H2A,H2B), O3(H3A,H3B), O4(H4A,H4B), O6(H6A,H6B), O7(H7A,H7B)
6.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C0AA(H0AA), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11),
 C13(H13), C14(H14), C15(H15), C16(H16), C19(H19), C20(H20), C21(H21), C22(H22),
  C23(H23), C24(H24), C25(H25), C30(H30), C31(H31), C32(H32), C36(H36),
 C37(H37), C38(H38), C39(H39), C40(H40), C43(H43), C44(H44), C46(H46), C47(H47),
  C50(H50), C56(H56), C61(H61), C62(H62), C63(H63), C64(H64), C67(H67),
 C68(H68), C69(H69), C70(H70), C72(H72), C73(H73), C74(H74), C75(H75), C78(H78),
  C79(H79), C80(H80), C81(H81), C82(H82), C83(H83), C84(H84), C89(H89),
 C90(H90), C91(H91), C95(H95), C96(H96), C97(H97), C98(H98), C99(H99),
 C102(H102), C103(H103), C105(H105), C106(H106), C110(H110), C116(H116),
 C123(H123), C124(H124), C125(H125), C126(H126), C127(H127), C129(H129),
 C130(H130), C131(H131), C132(H132), C133(H133), C137(H137), C138(H138),
 C139(H139), C140(H140), C141(H141)
6.c Fitted hexagon refined as free rotating group:
 C129(C130,C131,C132,C133,C134), C136(C137,C138,C139,C140,C141)
6.d Idealised Me refined as rotating group:
 C52(H52A,H52B,H52C), C53(H53A,H53B,H53C), C58(H58A,H58B,H58C), C59(H59A,H59B,
 H59C), C112(H11A,H11B,H11C), C113(H11D,H11E,H11F), C118(H11G,H11H,H11I),
 C119(H11J,H11K,H11L), C121(H12A,H12B,H12C), C128(H12D,H12E,H12F), C135(H13A,
 H13B,H13C)
;
_shelx_res_checksum              17273
_shelx_hkl_checksum              11310
_olex2_submission_special_instructions 'No special instructions were received'