One-pot synthesis of unsymmetrical biaryls from suitably functionalized 2H-pyran-2-ones through carbanion-induced ring-transformation reactions
Ram, Vishnu J.; Srivastava, Pratibha; Agarwal, Nidhi; Sharon, Ashoke; Maulik, Prakas R.; Journal of the Chemical Society, Perkin Transactions 1  (2001) 1953–; doi:10.1039/b009725j

data_7213461
_publ_contact_author             'Dr Vishnu Ji Ram'
_publ_section_title
;
 One-pot synthesis of unsymmetrical biaryls from suitably functionalized
 2H-pyran-2-ones through carbanion-induced ring-transformation reactions
;
_journal_issue                   16
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 1'
_journal_page_first              1953
_journal_paper_doi               10.1039/b009725j
_journal_year                    2001
_chemical_formula_sum            'C25 H23 Cl N4'
_chemical_formula_weight         414.92
_chemical_melting_point          152
_chemical_name_systematic
; 
4-(4-chlorophenyl)-2-(2-pyridyl piperazino)-6-cyclopropyl 
benzonitrile 
;
_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
_cell_angle_alpha                75.020(10)
_cell_angle_beta                 83.190(10)
_cell_angle_gamma                81.700(10)
_cell_formula_units_Z            4
_cell_length_a                   8.4520(10)
_cell_length_b                   12.3980(10)
_cell_length_c                   21.137(2)
_cell_measurement_reflns_used    41
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      12.5
_cell_measurement_theta_min      4.9
_cell_volume                     2109.6(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       \q-2\q
_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  0.0277
_diffrn_reflns_av_sigmaI/netI    0.0360
_diffrn_reflns_limit_h_max       1
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            8892
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.76
_diffrn_standards_decay_%        nil
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.201
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.425
_exptl_crystal_size_mid          0.352
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.618
_refine_diff_density_min         -0.588
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.0073(12)
_refine_ls_extinction_expression Fc^*^=3DkFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.962
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     542
_refine_ls_number_reflns         7258
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.962
_refine_ls_R_factor_all          0.0821
_refine_ls_R_factor_gt           0.0554
_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=3D1/[\s^2^(Fo^2^)+(0.0816P)^2^+1.7264P] where P=3D(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1427
_refine_ls_wR_factor_ref         0.1705
_reflns_number_gt                5254
_reflns_number_total             7258
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b009725jsup1.cif
_cod_data_source_block           6q
_cod_database_code               7213461