Delayed release singlet oxygen sensitizers based on pyridone-appended porphyrins
Callaghan, Susan; Filatov, Mikhail A.; Sitte, Elisabeth; Savoie, Huguette; Boyle, Ross W.; Flanagan, Keith; Senge, Mathias O.; Photochem. Photobiol. Sci.  (2017) –; doi:10.1039/C7PP00244K

data_1546795
_publ_section_title
;
 Delayed release singlet oxygen sensitizers based on pyridone-appended
 porphyrins
;
_journal_name_full               'Photochem. Photobiol. Sci.'
_journal_paper_doi               10.1039/C7PP00244K
_journal_year                    2017
_chemical_formula_moiety         'C68 H50 N8 O4, 4(H2 O)'
_chemical_formula_sum            'C68 H58 N8 O8'
_chemical_formula_weight         1115.22
_chemical_name_systematic
1,1',1'',1'''-((porphyrin-5,10,15,20-tetrayltetrakis(benzene-4,1-diyl))tetrakis(methylene))tetrakis(pyridin-2(1H)-one)
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2017-05-12
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2017-06-28 deposited with the CCDC.
2017-08-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.509(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   17.1886(10)
_cell_length_b                   7.6152(4)
_cell_length_c                   20.9922(11)
_cell_measurement_reflns_used    3230
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      63.80
_cell_measurement_theta_min      2.61
_cell_volume                     2701.7(3)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX 3 (Bruker, 2015) '
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device       'Kappa diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1757
_diffrn_reflns_av_unetI/netI     0.1264
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            32268
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        65.246
_diffrn_reflns_theta_max         65.246
_diffrn_reflns_theta_min         2.614
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.738
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_correction_T_min  0.4112
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1158 before and 0.0690 after correction. The Ratio of minimum to maximum transmission is 0.5464. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_description       plate
_exptl_crystal_F_000             1172
_exptl_crystal_recrystallization_method DCM/MeOH
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.526
_refine_diff_density_min         -0.386
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     385
_refine_ls_number_reflns         4549
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.1181
_refine_ls_R_factor_gt           0.0767
_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^)+(0.1223P)^2^+0.8341P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1949
_refine_ls_wR_factor_ref         0.2307
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2924
_reflns_number_total             4549
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7pp00244k2.cif
_cod_data_source_block           kjf073a
_cod_database_code               1546795
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.964
_shelx_estimated_absorpt_t_min   0.757
_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 O(H,H) groups
2.a Free rotating group:
 O2S(H2SA,H2SB), O1S(H1SA,H1SB)
2.b Secondary CH2 refined with riding coordinates:
 C207(H20A,H20B), C57(H57A,H57B)
2.c Aromatic/amide H refined with riding coordinates:
 N21(H21), C211(H211), C210(H210), C209(H209), C203(H203), C202(H202),
 C206(H206), C205(H205), C212(H212), C61(H61), C62(H62), C59(H59), C60(H60),
 C55(H55), C56(H56), C3(H3), C2(H2), C8(H8), C7(H7), C53(H53), C52(H52)
;
_shelx_res_checksum              56025
_olex2_exptl_crystal_mounting_method 'MitGen loop'
_olex2_submission_special_instructions 'No special instructions were received'