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_4038453
_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         'C48 H39 N3 S, C H4 O '
_chemical_formula_sum            'C49 H43 N3 O S'
_chemical_formula_weight         721.92
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 95.369(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.926(3)
_cell_length_b                   14.889(3)
_cell_length_c                   18.825(3)
_cell_measurement_reflns_used    2737
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      19.05
_cell_measurement_theta_min      2.57
_cell_volume                     3886.1(13)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.1186
_diffrn_reflns_av_unetI/netI     0.1633
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            50203
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_min         1.086
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.125
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_density_meas      1.235
_exptl_crystal_density_method    none
_exptl_crystal_description       block
_exptl_crystal_F_000             1528
_exptl_crystal_size_max          0.247
_exptl_crystal_size_mid          0.154
_exptl_crystal_size_min          0.085
_refine_diff_density_max         0.603
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details
;
 Flack x determined using 2470 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.32(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     941
_refine_ls_number_reflns         15264
_refine_ls_number_restraints     625
_refine_ls_restrained_S_all      0.979
_refine_ls_R_factor_all          0.1641
_refine_ls_R_factor_gt           0.0765
_refine_ls_shift/su_max          0.047
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0829P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1589
_refine_ls_wR_factor_ref         0.2029
_reflns_Friedel_coverage         0.921
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                7995
_reflns_number_total             15264
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00754_si_001.cif
_cod_data_source_block           shelx
_cod_original_cell_volume        3886.2(12)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4038453
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.970
_shelx_estimated_absorpt_t_max   0.989
_shelx_res_checksum              70105
_shelx_hkl_checksum              51467