Aromaticity control via modifications of a macrocyclic frame: 5,6-dimethoxyphenanthriporphyrin and 5,6-dioxophenanthriporphyrin
Kupietz, Kamil; Białek, Michał J.; Białońska, Agata; Szyszko, Bartosz; Latos-Grażyński, Lechosław; Organic Chemistry Frontiers 5 (2018) 3068–; doi:10.1039/C8QO00751A

data_1554400
_publ_section_title
;
 Aromaticity control via modifications of a macrocyclic frame:
 5,6-dimethoxyphenanthriporphyrin and 5,6-dioxophenanthriporphyrin
;
_journal_issue                   21
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              3068
_journal_paper_doi               10.1039/C8QO00751A
_journal_volume                  5
_journal_year                    2018
_chemical_formula_sum            'C43 H26 N2 O2'
_chemical_formula_weight         602.66
_chemical_name_systematic        5,6-dioxophenanthriporphyrin
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-07-19 deposited with the CCDC.
2018-08-20 downloaded from the CCDC.
;
_cell_angle_alpha                91.24(4)
_cell_angle_beta                 106.05(4)
_cell_angle_gamma                99.94(3)
_cell_formula_units_Z            2
_cell_length_a                   9.516(3)
_cell_length_b                   11.551(6)
_cell_length_c                   13.616(7)
_cell_measurement_reflns_used    415
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      78.49
_cell_measurement_theta_min      3.49
_cell_volume                     1412.9(12)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.20
_diffrn_measured_fraction_theta_full 0.916
_diffrn_measured_fraction_theta_max 0.863
_diffrn_measurement_device_type  'Xcalibur, Onyx'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.2960
_diffrn_reflns_av_unetI/netI     0.4114
_diffrn_reflns_Laue_measured_fraction_full 0.916
_diffrn_reflns_Laue_measured_fraction_max 0.863
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8357
_diffrn_reflns_point_group_measured_fraction_full 0.916
_diffrn_reflns_point_group_measured_fraction_max 0.863
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.468
_diffrn_reflns_theta_min         3.387
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.685
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_description       block
_exptl_crystal_F_000             628
_exptl_crystal_size_max          0.109
_exptl_crystal_size_mid          0.034
_exptl_crystal_size_min          0.027
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.089
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.895
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     424
_refine_ls_number_reflns         4981
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.895
_refine_ls_R_factor_all          0.3027
_refine_ls_R_factor_gt           0.1221
_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^)+(0.0086P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2214
_refine_ls_wR_factor_ref         0.3452
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1131
_reflns_number_total             4981
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo00751a2.cif
_cod_data_source_block           2
_cod_database_code               1554400
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.929
_shelx_estimated_absorpt_t_max   0.982
_shelx_res_checksum              5705
_shelx_hkl_checksum              86383