Facile Synthesis of Unsubstituted β,β'-Linked Diformyldipyrromethanes
Zhan Zhang; Ji-Young Shin; David Dolphin; Journal of Organic Chemistry 73 (2008) 9515–9517; doi:10.1021/jo802114h

data_4023913
_publ_contact_author_address
;Department of Chemistry,
University of British Columbia,
2036 Main Mall, Vancouver
BC V6T1Z1 Canada
;
_publ_contact_author_email       david.dolphin@ubc.ca
_publ_contact_author_fax         1-604-822-9678
_publ_contact_author_name        'David Dolphin'
_publ_contact_author_phone       1-604-822-4571
_publ_section_title
;
 Facile Synthesis of Unsubstituted \b,\b'-Linked
 Diformyldipyrromethanes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9515
_journal_page_last               9517
_journal_paper_doi               10.1021/jo802114h
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C11 H10 N2 O2'
_chemical_formula_weight         202.21
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.8943(12)
_cell_length_b                   4.5121(3)
_cell_length_c                   11.5662(8)
_cell_measurement_reflns_used    2962
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.64
_cell_measurement_theta_min      2.78
_cell_volume                     986.05(11)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker X8 APEX'
_diffrn_measurement_method       'area detector'
_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  0.0225
_diffrn_reflns_av_sigmaI/netI    0.0237
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7226
_diffrn_reflns_theta_full        27.84
_diffrn_reflns_theta_max         27.84
_diffrn_reflns_theta_min         2.16
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.828
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tablet
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     144
_refine_ls_number_reflns         2311
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0387
_refine_ls_R_factor_gt           0.0327
_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^)+(0.0476P)^2^+0.0908P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0813
_refine_ls_wR_factor_ref         0.0849
_reflns_number_gt                2069
_reflns_number_total             2311
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo802114h_si_001_1.cif
_cod_data_source_block           compound3
_cod_database_code               4023913