Steric control in the synthesis of p-benziporphyrins. Formation of a doubly N-confused benzihexaphyrin macrocycle.
Stepień, Marcin; Szyszko, Bartosz; Latos-Grazyński, Lechosław; Organic letters 11 (2009) 3930–3933; doi:10.1021/ol9016222

data_1504130
_publ_section_title
;
 Steric control in the synthesis of p-benziporphyrins. Formation of a
 doubly N-confused benzihexaphyrin macrocycle.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              3930
_journal_page_last               3933
_journal_paper_doi               10.1021/ol9016222
_journal_volume                  11
_journal_year                    2009
_chemical_formula_moiety         'C94 H96 N4 O2, 4(C H2 Cl2)'
_chemical_formula_sum            'C98 H104 Cl8 N4 O2'
_chemical_formula_weight         1653.45
_chemical_name_systematic
; 
 5,15,20,30-tetramesityl-10,25-diphenyl-8,23-dioxo-7,22-diaza-33,37-dicarba-A,D-di-p-benzi[28]hexaphyrin(1.1.1.1.1.1)
 dichloromethane tetrasolvate  
;
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method
;
1. CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.32 (release 27-01-2009 CrysAlis171 .NET)
(compiled Jan 27 2009,14:17:37)
2. SXELXL-97
;
_cell_angle_alpha                90.00
_cell_angle_beta                 105.354(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   14.7357(4)
_cell_length_b                   17.0703(3)
_cell_length_c                   17.6198(4)
_cell_measurement_reflns_used    15557
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      38.5079
_cell_measurement_theta_min      4.1289
_cell_volume                     4273.94(18)
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.32 (release 27-01-2009 CrysAlis171 .NET)
(compiled Jan 27 2009,14:17:37)
;
_computing_data_collection
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.33.32 (release 27-01-2009 CrysAlis171 .NET)
(compiled Jan 27 2009,14:17:37)
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.32 (release 27-01-2009 CrysAlis171 .NET)
(compiled Jan 27 2009,14:17:37)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.1956
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_details
;
  1 phi      0.00  100.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
   0.0000   14.0000    0.0000     -     100

  2 omega  -60.00   84.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       40.0000  -79.0000    0.0000 144

  3 omega  -60.00   84.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       40.0000  -79.0000  120.0000 144

  4 omega  -60.00   20.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       40.0000  -79.0000  240.0000 80

;
_diffrn_measurement_device_type  'Goniometer Xcalibur, detector: Onyx'
_diffrn_measurement_method       '\w and \p scans'
_diffrn_orient_matrix_UB_11      -0.0026235822
_diffrn_orient_matrix_UB_12      0.0265214582
_diffrn_orient_matrix_UB_13      -0.0315039908
_diffrn_orient_matrix_UB_21      -0.0470820511
_diffrn_orient_matrix_UB_22      0.0091471746
_diffrn_orient_matrix_UB_23      -0.0004968508
_diffrn_orient_matrix_UB_31      0.0163364260
_diffrn_orient_matrix_UB_32      0.0306523388
_diffrn_orient_matrix_UB_33      0.0273770661
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0523
_diffrn_reflns_av_sigmaI/netI    0.1103
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            66843
_diffrn_reflns_theta_full        38.59
_diffrn_reflns_theta_max         38.59
_diffrn_reflns_theta_min         4.14
_exptl_absorpt_coefficient_mu    0.316
_exptl_absorpt_correction_T_max  0.945
_exptl_absorpt_correction_T_min  0.886
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.32 (release 27-01-2009 CrysAlis171 .NET)
(compiled Jan 27 2009,14:17:37)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            dark
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1744
_exptl_crystal_size_max          0.4893
_exptl_crystal_size_mid          0.2659
_exptl_crystal_size_min          0.2364
_refine_diff_density_max         0.704
_refine_diff_density_min         -0.803
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.913
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     539
_refine_ls_number_reflns         23396
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.913
_refine_ls_R_factor_all          0.1334
_refine_ls_R_factor_gt           0.0552
_refine_ls_shift/su_max          0.026
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0708P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1291
_refine_ls_wR_factor_ref         0.1488
_reflns_number_gt                11814
_reflns_number_total             23396
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol9016222_si_002.cif
_cod_data_source_block           diamide
_cod_original_cell_volume        4273.94(17)
_cod_database_code               1504130