Facile synthesis of dicyanovinyl-di(meso-aryl)dipyrromethenes via a dipyrromethene–DDQ adduct
Shin, Ji-Young; Patrick, Brian O.; Dolphin, David; Organic & Biomolecular Chemistry 7 (2009) 2032–2035; doi:10.1039/b904446a

data_7150683
_publ_section_title
;
 Facile synthesis of dicyanovinyl-di(meso-aryl)dipyrromethenes via a
 dipyrromethene--DDQ adduct
;
_journal_issue                   10
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_page_first              2032
_journal_page_last               2035
_journal_paper_doi               10.1039/b904446a
_journal_volume                  7
_journal_year                    2009
_chemical_formula_sum            'C22 H11 Cl4 N3 O3'
_chemical_formula_weight         507.14
_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                84.895(5)
_cell_angle_beta                 77.368(5)
_cell_angle_gamma                81.828(5)
_cell_formula_units_Z            2
_cell_length_a                   7.8137(8)
_cell_length_b                   9.9057(11)
_cell_length_c                   14.0837(16)
_cell_measurement_reflns_used    9847
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.02
_cell_measurement_theta_min      2.69
_cell_volume                     1051.0(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker X8 APEX II'
_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  0.0287
_diffrn_reflns_av_sigmaI/netI    0.0183
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            36857
_diffrn_reflns_theta_full        28.09
_diffrn_reflns_theta_max         28.09
_diffrn_reflns_theta_min         1.48
_exptl_absorpt_coefficient_mu    0.595
_exptl_absorpt_correction_T_max  0.931
_exptl_absorpt_correction_T_min  0.864
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.603
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.367
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         5085
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0302
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0372P)^2^+0.4861P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0740
_refine_ls_wR_factor_ref         0.0787
_reflns_number_gt                4365
_reflns_number_total             5085
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b904446a.txt
_cod_data_source_block           dd308
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7150683