Synthesis and metalation of dimethoxybenziporphyrins, thiabenziporphyrins, and dibenziporphyrins.
Fosu, Stacy C.; Ferrence, Gregory M.; Lash, Timothy D.; The Journal of organic chemistry 79 (2014) 11061–11074; doi:10.1021/jo502063w

data_4030120
_publ_section_title
;
 Synthesis and metalation of dimethoxybenziporphyrins,
 thiabenziporphyrins, and dibenziporphyrins.
;
_journal_issue                   22
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11061
_journal_page_last               11074
_journal_paper_doi               10.1021/jo502063w
_journal_volume                  79
_journal_year                    2014
_chemical_formula_moiety         'C49 H36 N2 O2 S1, 0.5(C6 H14)'
_chemical_formula_sum            'C52 H43 N2 O2 S'
_chemical_formula_weight         759.94
_chemical_name_systematic
;
 2,4-Dimethoxy-3-methyl-6,11,16,21-tetraphenyl-
24-thiabenziporphyrin
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-06-17T14:35:06-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                117.9910(10)
_cell_angle_beta                 107.0500(10)
_cell_angle_gamma                92.9020(10)
_cell_formula_units_Z            2
_cell_length_a                   13.0557(4)
_cell_length_b                   13.3816(4)
_cell_length_c                   13.8875(4)
_cell_measurement_reflns_used    9212
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.89
_cell_measurement_theta_min      2.59
_cell_volume                     1996.69(11)
_computing_cell_refinement       'APEX2 & SAINT (Bruker, 2013)'
_computing_data_collection       'APEX2 (Bruker, 2013)'
_computing_data_reduction        SAINT
_computing_molecular_graphics
;
<i>Ortep-3</i> for Windows (Farrugia, 2012) and <i>Mercury CSD</i> (Macrae et
 al., 2008)
;
_computing_publication_material
;
        <i>WinGX</i> (Farrugia, 2012) and <i>publCIF</i> (Westrip, 2010)
;
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2012)'
_computing_structure_solution    'SUPERFLIP (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measurement_details
;
A total of 3672 frames were collected.  The total 
exposure time was 10.20 hours.
;
_diffrn_measurement_device_type  'Bruker APEX-II CCD diffractometer'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_av_unetI/netI     0.0159
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            79468
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         32.142
_diffrn_reflns_theta_min         1.674
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_correction_T_min  0.7124
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Apex2 v2013.2-0 (Bruker, 2013)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             802
_exptl_crystal_size_max          0.328
_exptl_crystal_size_mid          0.273
_exptl_crystal_size_min          0.162
_platon_squeeze_details
;
One hexane molecule has 50 electrons.  The strucutre 
could be refined with the hexane included, but 
there was significant residual electron density, 
which could not be adequately modeled and the 
C-C distance about the crystallographic 
inversion center refined as unrealistically short.
;
_refine_diff_density_max         0.559
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     494
_refine_ls_number_reflns         13237
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0418
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0737P)^2^+0.4528P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1207
_reflns_number_gt                11588
_reflns_number_total             13237
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo502063w_si_001.cif
_cod_data_source_block           shelx
_cod_depositor_comments
'Adding full bibliography for 4030120--4030121.cif.'
_cod_original_cell_volume        1996.68(10)
_cod_database_code               4030120
_shelxl_version_number           0.000002012