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_1554401
_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_moiety         'C43 H27 N2 O2, 3(C6 H6), B F4'
_chemical_formula_sum            'C61 H45 B F4 N2 O2'
_chemical_formula_weight         924.80
_chemical_name_systematic        'monocation of 5,6-dioxophenanthriporphyrin'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 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                90
_cell_angle_beta                 106.78(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.154(3)
_cell_length_b                   17.553(3)
_cell_length_c                   19.832(3)
_cell_measurement_reflns_used    9442
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.9931
_cell_measurement_theta_min      2.3250
_cell_volume                     4717.4(16)
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_data_collection
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.1956
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Xcalibur, Onyx'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54175
_diffrn_reflns_av_R_equivalents  0.0460
_diffrn_reflns_av_unetI/netI     0.0477
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            18917
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.676
_diffrn_reflns_theta_max         68.103
_diffrn_reflns_theta_min         3.416
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.721
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            blueish
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_description       plate
_exptl_crystal_F_000             1928
_exptl_crystal_size_max          0.538
_exptl_crystal_size_mid          0.422
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.420
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.947
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     639
_refine_ls_number_reflns         8435
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.947
_refine_ls_R_factor_all          0.0708
_refine_ls_R_factor_gt           0.0564
_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^)+(0.1159P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1492
_refine_ls_wR_factor_ref         0.1600
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6112
_reflns_number_total             8435
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo00751a2.cif
_cod_data_source_block           2H+
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1554401
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              8731
_shelx_hkl_checksum              93931