Push-pull quinoidal porphyrins.
Smith, Martin J.; Blake, Iain M.; Clegg, William; Anderson, Harry L.; Organic & biomolecular chemistry 16 (2018) 3648–3654; doi:10.1039/c8ob00491a

data_7156223
_publ_section_title
;
 Push-pull quinoidal porphyrins.
;
_journal_issue                   19
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3648
_journal_page_last               3654
_journal_paper_doi               10.1039/c8ob00491a
_journal_volume                  16
_journal_year                    2018
_chemical_formula_moiety         'C54 H52 N8'
_chemical_formula_sum            'C54 H52 N8'
_chemical_formula_weight         813.03
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_symmetry_space_group_name_Hall  '-I 2ya'
_symmetry_space_group_name_H-M   'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/1
_audit_update_record
;
2018-02-05 deposited with the CCDC.
2018-04-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.378(10)
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   34.85(3)
_cell_length_b                   13.785(11)
_cell_length_c                   40.21(3)
_cell_measurement_reflns_used    5490
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      22.14
_cell_measurement_theta_min      2.27
_cell_volume                     19301(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'SHELXL and local programs'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.893
_diffrn_measured_fraction_theta_max 0.893
_diffrn_measurement_device_type  'Bruker SMART 1K CCD diffractometer'
_diffrn_measurement_method       'thin-slice \w scans'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.6893
_diffrn_reflns_av_R_equivalents  0.1012
_diffrn_reflns_av_unetI/netI     0.1476
_diffrn_reflns_Laue_measured_fraction_full 0.893
_diffrn_reflns_Laue_measured_fraction_max 0.893
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            33400
_diffrn_reflns_point_group_measured_fraction_full 0.893
_diffrn_reflns_point_group_measured_fraction_max 0.893
_diffrn_reflns_theta_full        23.677
_diffrn_reflns_theta_max         23.677
_diffrn_reflns_theta_min         2.269
_diffrn_source                   'Daresbury SRS station 9.8'
_exptl_absorpt_coefficient_mu    0.063
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.119
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             6912
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: aqueous methanol'
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.030
_refine_diff_density_max         1.229
_refine_diff_density_min         -0.445
_refine_diff_density_rms         0.096
_refine_ls_extinction_coef       0.00044(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.142
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1202
_refine_ls_number_reflns         14281
_refine_ls_number_restraints     3291
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.2429
_refine_ls_R_factor_gt           0.1812
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1111P)^2^+309.8881P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3842
_refine_ls_wR_factor_ref         0.4153
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8224
_reflns_number_total             14281
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob00491a2.cif
_cod_data_source_block           oxdp22_H29
_cod_depositor_comments
'Adding full bibliography for 7156219--7156223.cif.'
_cod_original_cell_volume        19302(26)
_cod_database_code               7156223
_shelx_shelxl_version_number     2018/1
_shelx_estimated_absorpt_t_min   0.986
_shelx_estimated_absorpt_t_max   0.998
_shelx_res_checksum              41402
_shelx_fab_checksum              80793