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_1546796
_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         'C48 H34 Br4 N4'
_chemical_formula_sum            'C48 H34 Br4 N4'
_chemical_formula_weight         986.43
_chemical_name_systematic
5,10,15,20-tetrakis(4-(bromomethyl)phenyl)porphyrin
_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   geom
_atom_sites_solution_primary     direct
_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                 107.3000(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   15.8019(13)
_cell_length_b                   8.9658(7)
_cell_length_c                   14.5051(12)
_cell_measurement_reflns_used    8426
_cell_measurement_temperature    100
_cell_measurement_theta_max      29.018
_cell_measurement_theta_min      2.643
_cell_volume                     1962.1(3)
_computing_cell_refinement       'SAINT+ Ver. 8.34A (Bruker, 2014)'
_computing_data_collection       'APEX2 Ver. v.7-1 (Bruker, 2014)'
_computing_data_reduction        'SAINT+ Ver. 8.34A (Bruker, 2014)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.01
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'Kappa diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0500
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            37651
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.168
_diffrn_reflns_theta_min         2.643
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.144
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.5828
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0739 before and 0.0436 after correction.
The Ratio of minimum to maximum transmission is 0.7814.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.670
_exptl_crystal_description       plate
_exptl_crystal_F_000             980
_exptl_crystal_recrystallization_method DCM/MeOH
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.07
_refine_diff_density_max         1.355
_refine_diff_density_min         -1.106
_refine_diff_density_rms         0.106
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         5288
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0570
_refine_ls_R_factor_gt           0.0370
_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^)+(0.0475P)^2^+2.9923P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0885
_refine_ls_wR_factor_ref         0.0964
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4085
_reflns_number_total             5288
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7pp00244k2.cif
_cod_data_source_block           kjf079
_cod_database_code               1546796
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.760
_shelx_estimated_absorpt_t_min   0.539
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C107(H10A,H10B), C57(H57A,H57B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C7(H7), C3(H3), C8(H8), C105(H105), C106(H106), C2(H2A), C103(H103),
 C102(H102), C52(H52), C53(H53), C55(H55), C56(H56)
;
_shelx_res_checksum              48476
_olex2_date_sample_data_collection 2016-01-29
_olex2_date_sample_submission    2016-01-22
_olex2_exptl_crystal_mounting_method 'MiTeGen loop'
_olex2_submission_original_sample_id
5,10,15,20-tetrakis(4-(bromomethyl)phenyl)porphyrin
_olex2_submission_special_instructions 'No special instructions were received'