Zirconocene-Mediated Intermolecular Coupling of One Molecule of Si-Tethered Diyne with Three Molecules of Organonitriles: One-Pot Formation of Pyrrolo[3,2-c]pyridine Derivatives via Cleavage of C\τbN Triple Bonds of Organonitriles
Xiaohua Sun; Congyang Wang; Zhiping Li; Shiwei Zhang; Zhenfeng Xi; Journal of the American Chemical Society 126 (2004) 7172–7173; doi:10.1021/ja0497173

data_4112670
_publ_section_title
;
 Zirconocene-Mediated Intermolecular Coupling of One Molecule of
 Si-Tethered Diyne with Three Molecules of Organonitriles: One-Pot
 Formation of Pyrrolo[3,2-c]pyridine Derivatives via Cleavage of C\\tbN
 Triple Bonds of Organonitriles
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7172
_journal_page_last               7173
_journal_paper_doi               10.1021/ja0497173
_journal_volume                  126
_journal_year                    2004
_chemical_formula_sum            'C40 H32 N2'
_chemical_formula_weight         540.68
_space_group_IT_number           43
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'F 2 -2d'
_symmetry_space_group_name_H-M   'F d d 2'
_atom_sites_solution_hydrogens
'hydrogen atoms are generated by HFIX instructions'
_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            16
_cell_length_a                   24.991(5)
_cell_length_b                   51.872(10)
_cell_length_c                   9.933(2)
_cell_measurement_reflns_used    19238
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.24
_cell_volume                     12876(4)
_computing_cell_refinement
;
Molecular Structure Corporation (1994)
MSC/AFC Diffractometer Control Software
MSC, 3200 Research Forest Drive, The
Woodlands, TX 77381, USA.
;
_computing_data_collection
;
Molecular Structure Corporation (1994)
MSC/AFC Diffractometer Control Software
MSC, 3200 Research Forest Drive, The
Woodlands, TX 77381, USA.
;
_computing_data_reduction
;
Sheldrick, G. M. (1998) SHELXS98, Program
for the Solution of Crystal Structure,
University of Gottingen, Germany.
;
_computing_molecular_graphics
;
Interactive Molecular Graphics XP, Virsion
4.2 for MSDOS (1990), Siemens Analytical
X-ray Instruments Inc., Madison, Wisconsin,
USA.
;
_computing_publication_material
;
Sheldrick, G. M. (1998) SHELXL98, Program
for the Refinement of Crystal Structure,
University of Gottingen, Germany.
;
_computing_structure_refinement
;
Sheldrick, G. M. (1998) SHELXL98, Program
for the Refinement of Crystal Structure,
University of Gottingen, Germany.
;
_computing_structure_solution
;
Sheldrick, G. M. (1998) SHELXS98, Program
for the Solution of Crystal Structure,
University of Gottingen, Germany.
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean '100x100 microns'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Rigaku RAXIS RAPID IP'
_diffrn_measurement_method       Oscillation
_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  0.0462
_diffrn_reflns_av_sigmaI/netI    0.0796
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       67
_diffrn_reflns_limit_k_min       -67
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            19238
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.24
_exptl_absorpt_coefficient_mu    0.065
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.558
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.116
_exptl_crystal_description       Block
_exptl_crystal_F_000             4576
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   4(6)
_refine_ls_extinction_coef       0.00298(17)
_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   1.023
_refine_ls_hydrogen_treatment
;
hydrogen coordinates ride on the coordinates
of the previous atom, the isotropic U values
are 1.2 OR 1.5 time over the U values of the
previous atom.
;
_refine_ls_matrix_type           full
_refine_ls_number_parameters     380
_refine_ls_number_reflns         3891
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.1055
_refine_ls_R_factor_gt           0.0549
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0648P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1398
_refine_ls_wR_factor_ref         0.1505
_reflns_number_gt                1836
_reflns_number_total             3891
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0497173si20040120_050547.cif
_cod_data_source_block           a
_cod_original_cell_volume        12877(4)
_cod_database_code               4112670