1,3-Dipolar Cycloaddition of 2,6-Dichlorobenzonitrile Oxide to 2-Methyl-N-confused Porphyrin. Regio- and Stereoselective Synthesis and Structural Characterization of 2-Aza-21-carbabacteriochlorin and Resolution of 2-Aza-21-carbachlorin Enantiomers
Xiaofang Li; Bin Liu; Xianyong Yu; Pinggui Yi; Rongqiong Yi; Piotr J. Chmielewski; Journal of Organic Chemistry 77 (2012) 2431–2440; doi:10.1021/jo3000817

data_4027052
_publ_section_title
;
 1,3-Dipolar Cycloaddition of 2,6-Dichlorobenzonitrile Oxide to
 2-Methyl-N-confused Porphyrin. Regio- and Stereoselective Synthesis and
 Structural Characterization of 2-Aza-21-carbabacteriochlorin and
 Resolution of 2-Aza-21-carbachlorin Enantiomers
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2431
_journal_page_last               2440
_journal_paper_doi               10.1021/jo3000817
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety
'C59 H37 Cl4 N6 O2, 1.5(C H Cl3), 0.5(C6 H14)'
_chemical_formula_sum            'C63.5 H45.5 Cl8.5 N6 O2'
_chemical_formula_weight         1225.88
_chemical_name_systematic
; 
 ? 
;
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 102.235(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.1898(5)
_cell_length_b                   27.8850(10)
_cell_length_c                   17.4845(7)
_cell_measurement_reflns_used    7902
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      36.7038
_cell_measurement_theta_min      2.9944
_cell_volume                     5808.2(4)
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET)
(compiled May 29 2009,17:40:42)
;
_computing_data_collection
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET)
(compiled May 29 2009,17:40:42)
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET)
(compiled May 29 2009,17:40:42)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       '\w and \p scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0773
_diffrn_reflns_av_sigmaI/netI    0.1210
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            35944
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.00
_exptl_absorpt_coefficient_mu    0.462
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_description       block
_exptl_crystal_F_000             2516
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         1.110
_refine_diff_density_min         -0.758
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.939
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     748
_refine_ls_number_reflns         10211
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.939
_refine_ls_R_factor_all          0.1398
_refine_ls_R_factor_gt           0.0627
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0800P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1463
_refine_ls_wR_factor_ref         0.1628
_reflns_number_gt                4929
_reflns_number_total             10211
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo3000817_si_002.cif
_cod_data_source_block           chin63
_cod_original_formula_sum        'C63.50 H45.50 Cl8.50 N6 O2'
_cod_database_code               4027052