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_4027051
_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         'C52 H35 Cl2 N5 Ni0.05 O'
_chemical_formula_sum            'C52 H35 Cl2 N5 Ni0.05 O'
_chemical_formula_weight         819.69
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                72.112(7)
_cell_angle_beta                 68.340(7)
_cell_angle_gamma                75.152(6)
_cell_formula_units_Z            2
_cell_length_a                   12.1600(8)
_cell_length_b                   13.2309(9)
_cell_length_c                   13.6965(10)
_cell_measurement_reflns_used    2683
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      38.5426
_cell_measurement_theta_min      2.5787
_cell_volume                     1923.4(3)
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET)
(compiled Sep 15 2009,11:49:04)
;
_computing_data_collection
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET)
(compiled Sep 15 2009,11:49:04)
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET)
(compiled Sep 15 2009,11:49:04)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'Xcalibur with Onyx CCD'
_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  0.0614
_diffrn_reflns_av_sigmaI/netI    0.1666
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14414
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.58
_exptl_absorpt_coefficient_mu    0.243
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'dark green'
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_description       block
_exptl_crystal_F_000             850.8
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.715
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.824
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     542
_refine_ls_number_reflns         6532
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.824
_refine_ls_R_factor_all          0.1656
_refine_ls_R_factor_gt           0.0649
_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^)+(0.0700P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1414
_refine_ls_wR_factor_ref         0.1587
_reflns_number_gt                2526
_reflns_number_total             6532
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo3000817_si_001.cif
_cod_data_source_block           chin6261
_cod_original_cell_volume        1923.4(2)
_cod_database_code               4027051