Synthesis of Benziporphyrins and Heterobenziporphyrins and an Assessment of the Diatropic Characteristics of the Protonated Species
Timothy D. Lash; Ashley M. Toney; Kylie M. Castans; Gregory M. Ferrence; Journal of Organic Chemistry 78 (2013) 9143–9152; doi:10.1021/jo401365p

data_4028600
_publ_contact_author_address
;
CB 4160
Department of Chemistry
Illinois State University
Normal, IL 61790-4160
USA
;
_publ_contact_author_email       ferrence@ilstu.edu
_publ_contact_author_fax         (309)438-5538
_publ_contact_author_name        'Ferrence, Gregory M.'
_publ_contact_author_phone       (309)438-7971
_publ_section_title
;
 Synthesis of Benziporphyrins and Heterobenziporphyrins and an Assessment
 of the Diatropic Characteristics of the Protonated Species
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9143
_journal_page_last               9152
_journal_paper_doi               10.1021/jo401365p
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C42  H37  N3  Pd1, 0.5 C6 H14'
_chemical_formula_sum            'C45 H44 N3 Pd'
_chemical_formula_weight         733.23
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_creation_date             2013-07-28T15:53:36-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 105.406(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.3442(3)
_cell_length_b                   29.4631(8)
_cell_length_c                   11.8597(3)
_cell_measurement_reflns_used    9379
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.63
_cell_measurement_theta_min      2.25
_cell_volume                     3484.63(17)
_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 0.999
_diffrn_measurement_details
;
2556 frames were collected.  The total exposure time was 127.80 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  0.1082
_diffrn_reflns_av_unetI/netI     0.0708
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            82747
_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         29.306
_diffrn_reflns_theta_min         1.382
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.57
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.588
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Apex2 v2013.2-0 (Bruker, 2013)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_description       needle
_exptl_crystal_F_000             1524
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.005
_platon_squeeze_details
;
Residual electron density consistent with disordered hexane was clearly
 identified, but no suitable model for the hexane was found.  The electron
 density was near special positions.  SQUEEZE was used to 'remove' the solvent.
 SQUEEZE found 58 electrons in the voids which contained the hexane 
(50 electrons). 
;
_refine_diff_density_max         0.644
_refine_diff_density_min         -1.173
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     420
_refine_ls_number_reflns         9535
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0851
_refine_ls_R_factor_gt           0.0467
_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^)+(0.0424P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0929
_reflns_number_gt                6719
_reflns_number_total             9535
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo401365p_si_004.cif
_cod_data_source_block           gmf13051_0m
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4028600
_shelxl_version_number           0.000002012