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_1554402
_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
'2(C43 H27 B F2 N2 O2), 3(B2 F6 O) [+ solvent]'
_chemical_formula_sum            'C86 H54 B8 F22 N4 O7'
_chemical_formula_weight         1759.81
_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                82.58(2)
_cell_angle_beta                 89.11(2)
_cell_angle_gamma                70.85(3)
_cell_formula_units_Z            1
_cell_length_a                   8.090(2)
_cell_length_b                   12.074(3)
_cell_length_c                   24.254(3)
_cell_measurement_reflns_used    1241
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      80.2418
_cell_measurement_theta_min      1.8361
_cell_volume                     2218.3(9)
_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 0.996
_diffrn_measured_fraction_theta_max 0.948
_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  0.1544
_diffrn_reflns_av_unetI/netI     0.2807
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            22839
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        67.676
_diffrn_reflns_theta_max         80.508
_diffrn_reflns_theta_min         1.838
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.986
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            maroon
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_description       needle
_exptl_crystal_F_000             892
_exptl_crystal_size_max          0.654
_exptl_crystal_size_mid          0.041
_exptl_crystal_size_min          0.035
_refine_diff_density_max         0.392
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.664
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     632
_refine_ls_number_reflns         9238
_refine_ls_number_restraints     120
_refine_ls_restrained_S_all      0.687
_refine_ls_R_factor_all          0.2001
_refine_ls_R_factor_gt           0.0810
_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^)+(0.0923P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1883
_refine_ls_wR_factor_ref         0.2196
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2150
_reflns_number_total             9238
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo00751a2.cif
_cod_data_source_block           2BF2
_cod_database_code               1554402
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.565
_shelx_estimated_absorpt_t_max   0.966
_shelx_res_checksum              70274
_shelx_hkl_checksum              26045
_shelx_fab_checksum              16785