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_7213460
_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            'C29 H22 Cl F2 N3 O2'
_chemical_formula_weight         517.95
_chemical_melting_point          220
_chemical_name_systematic
; 
3-cyano-6-(4-chlorophenyl)-4-[Bis(4-fluorophenyl)piperazino]-2H-pyran-2-one
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 92.71
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   44.292(4)
_cell_length_b                   7.6620(10)
_cell_length_c                   14.9490(10)
_cell_measurement_reflns_used    47
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      12.3
_cell_measurement_theta_min      2.7
_cell_volume                     5067.5(9)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0330
_diffrn_reflns_av_sigmaI/netI    0.0717
_diffrn_reflns_limit_h_max       52
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       1
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5388
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.70
_diffrn_standards_decay_%        nil
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.198
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellowish
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             2144
_exptl_crystal_size_max          0.375
_exptl_crystal_size_mid          0.275
_exptl_crystal_size_min          0.075
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         4445
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.1369
_refine_ls_R_factor_gt           0.0584
_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^)+(0.0710P)^2^+0.0000P] where P=3D(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1240
_refine_ls_wR_factor_ref         0.1572
_reflns_number_gt                2219
_reflns_number_total             4445
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b009725jsup1.cif
_cod_data_source_block           5h
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7213460