Unexpected Ring Transformation to Pyrrolo[3.2-b]pyridine Derivatives. Fused Azolium Salts. 22
Zsuzsanna Riedl; Péter Kövér; György Hajós; Orsolya Egyed; László Fábián; András Messmer; Journal of Organic Chemistry 68 (2003) 5652–5659; doi:10.1021/jo034231a

data_4022422
_publ_section_title
;
 Unexpected Ring Transformation to Pyrrolo[3.2-b]pyridine Derivatives.
 Fused Azolium Salts. 22
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5652
_journal_page_last               5659
_journal_paper_doi               10.1021/jo034231a
_journal_volume                  68
_journal_year                    2003
_chemical_formula_sum            'C21 H14 Cl2 N4 S'
_chemical_formula_weight         425.32
_chemical_name_systematic
;
 kp83
;
_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                 99.305(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.904(1)
_cell_length_b                   18.298(1)
_cell_length_c                   10.284(1)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      39.73
_cell_measurement_theta_min      35.04
_cell_volume                     2024.9(3)
_computing_cell_refinement       'CAD4 Express'
_computing_data_collection       'CAD4 Express'
_computing_data_reduction        'XCAD4 (Harms 1996)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Enraf-Nonius CAD4'
_diffrn_measurement_method       \w--2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'CU k\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0568
_diffrn_reflns_av_sigmaI/netI    0.0290
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4593
_diffrn_reflns_theta_full        75.87
_diffrn_reflns_theta_max         75.87
_diffrn_reflns_theta_min         4.11
_diffrn_standards_decay_%        4
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    3.959
_exptl_absorpt_correction_T_max  0.6729
_exptl_absorpt_correction_T_min  0.5308
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   'DATCOR (Riebenspies, 1989)'
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.412
_refine_diff_density_min         -0.471
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       0.0017(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         4217
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0670
_refine_ls_R_factor_gt           0.0510
_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^)+(0.1037P)^2^+0.1325P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1515
_refine_ls_wR_factor_ref         0.1596
_reflns_number_gt                3158
_reflns_number_total             4217
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo034231asi20030515_025854_4.cif
_cod_data_source_block           5b
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4022422