Synthesis, Structure and Optical Properties of Di-m-benzihexaphyrins (1.1.0.0.0.0) and Di-m-benziheptaphyrins (1.0.1.0.0.0.0): Blackening of m-Phenylene Linked Dicarbaporphyrinoids by Simple p-Expansion.
Sulfikarali, Thondikkal; Ajay, Jayaprakash; Suresh, Cherumuttathu H.; Bijina, Padinjare Veetil; Gokulnath, Sabapathi; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c00754

data_4038452
_publ_section_title
;
 Synthesis, Structure and Optical Properties of Di-m-benzihexaphyrins
 (1.1.0.0.0.0) and Di-m-benziheptaphyrins (1.0.1.0.0.0.0): Blackening of
 m-Phenylene Linked Dicarbaporphyrinoids by Simple p-Expansion.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00754
_journal_year                    2020
_chemical_formula_moiety         'C53 H42 Cl3 N3 S2'
_chemical_formula_sum            'C53 H42 Cl3 N3 S2'
_chemical_formula_weight         891.36
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 110.411(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.677(3)
_cell_length_b                   12.7097(16)
_cell_length_c                   20.926(3)
_cell_measurement_reflns_used    4684
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      20.84
_cell_measurement_theta_min      2.33
_cell_volume                     4655.5(12)
_computing_cell_refinement       'APEX3/SAINT (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2016)'
_computing_molecular_graphics    'ORTEP3- 2014.1(Farrugia, 1997) '
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker KAPPA APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0828
_diffrn_reflns_av_unetI/netI     0.0741
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            45024
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         1.909
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.326
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.954
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_meas      1.271
_exptl_crystal_density_method    none
_exptl_crystal_description       plate
_exptl_crystal_F_000             1856
_exptl_crystal_size_max          0.145
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.035
_refine_diff_density_max         0.728
_refine_diff_density_min         -0.696
_refine_diff_density_rms         0.071
_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     593
_refine_ls_number_reflns         8183
_refine_ls_number_restraints     150
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.1441
_refine_ls_R_factor_gt           0.0764
_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^)+(0.1306P)^2^+4.4471P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2006
_refine_ls_wR_factor_ref         0.2587
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4452
_reflns_number_total             8183
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00754_si_003.cif
_cod_data_source_block           shelx
_cod_original_cell_volume        4655.7(11)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4038452
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.954
_shelx_estimated_absorpt_t_max   0.989
_shelx_res_checksum              61438
_shelx_hkl_checksum              22823