A Supramolecular Approach for Modulated Photoprotection, Lysosomal Delivery, and Photodynamic Activity of a Photosensitizer.
Roy, Indranil; Bobbala, Sharan; Young, Ryan M.; Beldjoudi, Yassine; Nguyen, Minh T.; Cetin, M. Mustafa; Cooper, James A.; Allen, Sean; Anamimoghadam, Ommid; Scott, Evan A.; Wasielewski, Michael R.; Stoddart, J. Fraser; Journal of the American Chemical Society 141 (2019) 12296–12304; doi:10.1021/jacs.9b03990

data_4128658
_publ_section_title
;
 A Supramolecular Approach for Modulated Photoprotection, Lysosomal
 Delivery, and Photodynamic Activity of a Photosensitizer.
;
_journal_issue                   31
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12296
_journal_page_last               12304
_journal_paper_doi               10.1021/jacs.9b03990
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety
'2(C24 H20 N2), 2(C16 H11 N2), 4(F6 P), C3 H6 O, 2(C2 H3 N)'
_chemical_formula_sum            'C87 H74 F24 N10 O P4'
_chemical_formula_weight         1855.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yc'
_space_group_name_H-M_alt        'P 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2019-03-15
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                90
_cell_angle_beta                 104.239(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   31.4603(19)
_cell_length_b                   15.0357(9)
_cell_length_c                   20.4599(10)
_cell_measurement_reflns_used    9936
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      65.117
_cell_measurement_theta_min      2.898
_cell_volume                     9380.8(9)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       'APEX2 V2014.11-0 (Bruker, 2014)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      100.01
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker Kappa APEX CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_unetI/netI     0.0422
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            49019
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        65.236
_diffrn_reflns_theta_max         65.236
_diffrn_reflns_theta_min         1.449
_exptl_absorpt_coefficient_mu    1.594
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_correction_T_min  0.5944
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1239 before and 0.0528 after correction. The Ratio of minimum to maximum transmission is 0.7898. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_description       needle
_exptl_crystal_F_000             3800
_exptl_crystal_recrystallization_method
'The material was recrystallised from --- by as supplied'
_exptl_crystal_size_max          0.323
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.056
_refine_diff_density_max         0.833
_refine_diff_density_min         -0.578
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1230
_refine_ls_number_reflns         15796
_refine_ls_number_restraints     1302
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.1122
_refine_ls_R_factor_gt           0.0925
_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^)+(0.1569P)^2^+10.2138P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2636
_refine_ls_wR_factor_ref         0.2865
_reflns_Friedel_coverage         0.000
_reflns_number_gt                11672
_reflns_number_total             15796
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b03990_si_003.cif
_cod_data_source_block           Ex_Por
_cod_database_code               4128658
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.916
_shelx_estimated_absorpt_t_min   0.627
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 F23-F27 \\sim F23-F26 \\sim F23-F25 \\sim F23-F24 \\sim F27-F26 \\sim F27-F22
\\sim F27-F24 \\sim F26-F25
 \\sim F26-F22 \\sim F25-F22 \\sim F25-F24 \\sim F22-F24
 with sigma of 0.02
 P5-F23 \\sim P5-F27 \\sim P5-F26 \\sim P5-F25 \\sim P5-F22 \\sim P5-F24
 with sigma of 0.01
 F1-F6 \\sim F1-F5 \\sim F1-F4 \\sim F1-F3 \\sim F6-F2 \\sim F6-F5 \\sim F2-F5
\\sim F2-F4 \\sim F2-F3 \\sim F5-F4
 with sigma of 0.02
 P1-F1 \\sim P1-F6 \\sim P1-F2 \\sim P1-F5 \\sim P1-F4 \\sim P1-F3
 with sigma of 0.01
 F2-F5 \\sim F2-F4 \\sim F2-F3 \\sim F2-F6 \\sim F5-F4 \\sim F5-F6 \\sim F5-F1
\\sim F4-F3 \\sim F4-F1 \\sim F3-F6
 \\sim F3-F1 \\sim F6-F1
 with sigma of 0.02
 P1-F2 \\sim P1-F5 \\sim P1-F4 \\sim P1-F3 \\sim P1-F6 \\sim P1-F1
 with sigma of 0.01
 F4A-F2A \\sim F4A-F5A \\sim F4A-F3A \\sim F4A-F1A \\sim F2A-F5A \\sim F2A-F3A
\\sim F2A-F6A \\sim F5A-F1A
 \\sim F5A-F6A \\sim F3A-F1A \\sim F3A-F6A \\sim F1A-F6A
 with sigma of 0.02
 P1-F4A \\sim P1-F2A \\sim P1-F5A \\sim P1-F3A \\sim P1-F1A \\sim P1-F6A
 with sigma of 0.01
3. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(F1A)=Sof(F2A)=Sof(F3A)=Sof(F4A)=Sof(F5A)=Sof(F6A)=1-FVAR(1)
 Sof(F1)=Sof(F2)=Sof(F3)=Sof(F4)=Sof(F5)=Sof(F6)=FVAR(1)
 Fixed Sof: H3B(0.5) H4(0.5) H4A(0.5) P5(0.5) F22(0.5) F23(0.5) F24(0.5)
 F25(0.5) F26(0.5) F27(0.5) H3AA(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C18(H18A,H18B), C1A(H1AA,H1AB), C18A(H18C,H18D)
5.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C9(H9), C11(H11), C12(H12), C14(H14),
 C15(H15), C16(H16), C17(H17), C20(H20), C21(H21), C23(H23), C24(H24), C2A(H2A),
  C3A(H3A), C5A(H5A), C6A(H6A), C8A(H8A), C9A(H9A), C11A(H11A), C12A(H12A),
 C14A(H14A), C15A(H15A), C16A(H16A), C17A(H17A), C20A(H20A), C21A(H21A),
 C23A(H23A), C24A(H24A), N3(H3B), N4(H4), C25(H25), C27(H27), C28(H28),
 C32(H32), C33(H33), C36(H36), C37(H37), C38(H38), C39(H39), C40(H40), N4A(H4A),
  C25A(H25A), C27A(H27A), C28A(H28A), C32A(H32A), C33A(H33A), C36A(H36A),
 C37A(H37A), C38A(H38A), C39A(H39A), C40A(H40A)
5.c Idealised Me refined as rotating group:
 C2S(H2SA,H2SB,H2SC), C3S(H3SA,H3SB,H3SC), C5S(H5SA,H5SB,H5SC), C7S(H7SA,H7SB,
 H7SC)
;
_shelx_res_checksum              51614
_shelx_hkl_checksum              72611
_shelx_fab_checksum              2753
_olex2_date_sample_data_collection 2018-01-19
_olex2_date_sample_submission    2018-01-17
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder in Paratone oil'
_olex2_submission_original_sample_id cx1172
_olex2_submission_special_instructions 'No special instructions were received'