Synthesis, Characterization, and Biological Evaluation of New Ru(II) Polypyridyl Photosensitizers for Photodynamic Therapy.
Frei, Angelo; Rubbiani, Riccardo; Tubafard, Solmaz; Blacque, Olivier; Anstaett, Philipp; Felgenträger, Ariane; Maisch, Tim; Spiccia, Leone; Gasser, Gilles; Journal of medicinal chemistry 57 (2014) 7280–7292; doi:10.1021/jm500566f

data_1517447
_publ_section_title
;
 Synthesis, Characterization, and Biological Evaluation of New Ru(II)
 Polypyridyl Photosensitizers for Photodynamic Therapy.
;
_journal_issue                   17
_journal_name_full               'Journal of medicinal chemistry'
_journal_page_first              7280
_journal_page_last               7292
_journal_paper_doi               10.1021/jm500566f
_journal_volume                  57
_journal_year                    2014
_chemical_formula_moiety         'C46 H32 N6 O2 Ru, 2(F6 P)'
_chemical_formula_sum            'C46 H32 F12 N6 O2 P2 Ru'
_chemical_formula_weight         1091.78
_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_Hall           'F 2 -2d'
_space_group_name_H-M_alt        'F d d 2'
_symmetry_space_group_name_Hall  'F 2 -2d'
_symmetry_space_group_name_H-M   'F d d 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2013-10-04
_audit_creation_method
;
Olex2 1.2
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   43.6636(10)
_cell_length_b                   43.3688(7)
_cell_length_c                   9.2311(2)
_cell_measurement_reflns_used    9173
_cell_measurement_temperature    182(2)
_cell_measurement_theta_max      76.2389
_cell_measurement_theta_min      2.0357
_cell_volume                     17480.4(6)
_computing_cell_refinement
;
CrysAlisPro, version 1.171.36.20 (Agilent Technologies, 2012)
;
_computing_data_collection
;
CrysAlisPro, version 1.171.36.28 (Agilent Technologies, 2012)
;
_computing_data_reduction
;
CrysAlisPro, version 1.171.36.20 (Agilent Technologies, 2012)
;
_computing_molecular_graphics
;
<i>Mercury</i> (Macrae et al., 2006)
;
_computing_publication_material
; 
<i>WinGX</i> (Farrugia, 1999), <i>PLATON for Windows</i> (Spek, 2003) and
<i>publCIF</i> (Westrip, 2010)
;
_computing_structure_refinement  ' SHELXL2013 (Sheldrick, 2008)'
_computing_structure_solution
;
SUPERFLIP (Palatinus & Chapuis, 2007)
;
_diffrn_ambient_temperature      182(2)
_diffrn_detector_area_resol_mean 10.3801
_diffrn_measured_fraction_theta_full 0.9808
_diffrn_measured_fraction_theta_max 0.9980
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0056447000
_diffrn_orient_matrix_UB_12      -0.0350507000
_diffrn_orient_matrix_UB_13      0.0044783000
_diffrn_orient_matrix_UB_21      0.0055184000
_diffrn_orient_matrix_UB_22      0.0018115000
_diffrn_orient_matrix_UB_23      0.1645582000
_diffrn_orient_matrix_UB_31      -0.0343959000
_diffrn_orient_matrix_UB_32      -0.0054765000
_diffrn_orient_matrix_UB_33      0.0272131000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_limit_h_max       43
_diffrn_reflns_limit_h_min       -51
_diffrn_reflns_limit_k_max       52
_diffrn_reflns_limit_k_min       -47
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            16177
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.209
_diffrn_reflns_theta_min         2.872
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.489
_exptl_absorpt_correction_T_max  0.942
_exptl_absorpt_correction_T_min  0.557
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.659
_exptl_crystal_description       plate
_exptl_crystal_F_000             8768
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.835
_refine_diff_density_min         -0.625
_refine_diff_density_rms         0.104
_refine_ls_abs_structure_details
;
 Flack x determined using 2249 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.055(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     580
_refine_ls_number_reflns         6703
_refine_ls_number_restraints     289
_refine_ls_restrained_S_all      1.113
_refine_ls_R_factor_all          0.0802
_refine_ls_R_factor_gt           0.0782
_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^)+(0.0913P)^2^+264.6158P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2093
_refine_ls_wR_factor_ref         0.2110
_reflns_Friedel_coverage         0.581
_reflns_Friedel_fraction_full    0.662
_reflns_Friedel_fraction_max     0.661
_reflns_number_gt                6458
_reflns_number_total             6703
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jm500566f_si_002.cif
_cod_data_source_block           2
_cod_depositor_comments          'Adding full bibliography for 1517447.cif.'
_cod_database_code               1517447
_shelxl_version_number           2013-4
_reflns_odcompleteness_completeness 98.08
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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
2. Restrained distances
 F7A-F8A = F7A-F10A = F7A-F11A = F7A-F12A = F8A-F9A = F8A-F11A = F8A-F12A =
 F9A-F10A = F9A-F11A = F9A-F12A = F10A-F11A = F10A-F12A
 2.22 with sigma of 0.01
 F7B-F8B = F7B-F10B = F7B-F11B = F7B-F12B = F8B-F9B = F8B-F11B = F8B-F12B =
 F9B-F10B = F9B-F11B = F9B-F12B = F10B-F11B = F10B-F12B
 2.22 with sigma of 0.01
 P2-F7A \\sim P2-F8A \\sim P2-F9A \\sim P2-F10A \\sim P2-F11A \\sim P2-F12A
 with sigma of 0.005
 P2-F7B \\sim P2-F8B \\sim P2-F9B \\sim P2-F10B \\sim P2-F11B \\sim P2-F12B
 with sigma of 0.005
3. Uiso/Uaniso restraints and constraints
F7A \\sim F8A \\sim F9A \\sim F10A \\sim F11A \\sim F12A: within 3A with sigma
of 0.005 and sigma for terminal atoms of 0.01
F7B \\sim F8B \\sim F9B \\sim F10B \\sim F11B \\sim F12B: within 3A with sigma
of 0.005 and sigma for terminal atoms of 0.01
C41 \\sim C42 \\sim C43 \\sim C44 \\sim C45 \\sim C46: within 3A with sigma of
0.005 and sigma for terminal atoms of 0.01
4. Others
 Sof(F7B)=Sof(F8B)=Sof(F9B)=Sof(F10B)=Sof(F11B)=Sof(F12B)=1-FVAR(1)
 Sof(F7A)=Sof(F8A)=Sof(F9A)=Sof(F10A)=Sof(F11A)=Sof(F12A)=FVAR(1)
5.a :
 C41(C42,C43,C44,C45,C46,F1,F2,F3,F4,F5,F6,F7A,F8A,F9A,F10A,F11A,F12A,N1,N2,N3,
 N4,N5,N6,O1,O2,P1,Ru1,F7B,F8B,F9B,F10B,F11B,F12B,P2)
5.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C7(H7), C8(H8), C9(H9), C11(H11), C13(H13), C16(H16),
 C17(H17), C18(H18), C21(H21), C22(H22), C23(H23), C26(H26), C27(H27), C28(H28),
  C29(H29), C32(H32), C34(H34), C37(H37), C38(H38), C39(H39), C40(H40),
 C42(H42), C43(H43), C44(H44), C45(H45), C46(H46)
5.c Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C)
;