Orthogonal Synthesis of Densely Functionalized Pyrroles and Thiophenes from the Reactions of Imidazo[1,5-a]pyridine Carbene-Derived Zwitterions with Electron-Deficient Alkynes
Ying Cheng; Jiang-Hua Peng; Jia-Qi Li; Journal of Organic Chemistry 75 (2010) 2382–2388; doi:10.1021/jo100225r

data_4025348
_publ_section_title
;
 Orthogonal Synthesis of Densely Functionalized Pyrroles and Thiophenes
 from the Reactions of Imidazo[1,5-a]pyridine Carbene-Derived Zwitterions
 with Electron-Deficient Alkynes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2382
_journal_page_last               2388
_journal_paper_doi               10.1021/jo100225r
_journal_volume                  75
_journal_year                    2010
_chemical_formula_moiety         'C31 H23 Br Cl N3 O2 S'
_chemical_formula_sum            'C31 H23 Br Cl N3 O2 S'
_chemical_formula_weight         616.94
_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                 97.588(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.2162(12)
_cell_length_b                   15.3633(17)
_cell_length_c                   17.547(2)
_cell_measurement_reflns_used    5930
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.9
_cell_measurement_theta_min      1.8
_cell_volume                     2730.0(5)
_computing_cell_refinement       CrystalClear
_computing_data_collection       CrystalClear
_computing_data_reduction        CrystalClear
_computing_publication_material  'CrystalStructure 3.7.0'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  cofnocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0558
_diffrn_reflns_av_sigmaI/netI    0.0510
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            25264
_diffrn_reflns_theta_full        27.88
_diffrn_reflns_theta_max         27.88
_diffrn_reflns_theta_min         1.77
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.715
_exptl_absorpt_correction_T_max  0.7254
_exptl_absorpt_correction_T_min  0.6837
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'numabs (Rigaku, 2005)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1256
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.432
_refine_diff_density_min         -0.719
_refine_diff_density_rms         0.103
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     353
_refine_ls_number_reflns         6486
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0423
_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^)+(0.0571P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0979
_refine_ls_wR_factor_ref         0.1163
_reflns_number_gt                5373
_reflns_number_total             6486
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo100225r_si_001.cif
_cod_data_source_block           shelxl
_cod_original_cell_volume        2729.9(5)
_cod_database_code               4025348