Synthesis of Highly Functionalized Biaryls by Condensation of 2-Fluoro-1,3-bis(silyloxy) 1,3-Dienes with 3-Cyanochromones and Subsequent Domino "Retro-Michael/Aldol/Fragmentation"
Muhammad Farooq Ibad; Obaid-Ur-Rahman Abid; Muhammad Adeel; Muhammad Nawaz; Verena Wolf; Alexander Villinger; Peter Langer; Journal of Organic Chemistry 75 (2010) 8315–8318; doi:10.1021/jo1018443

data_4025858
_publ_contact_author_address
;
Universit\"at Rostock
Institut f\"ur Chemie
Abteilung f\"ur Organische Chemie
Albert-Einstein-Strasse 3a 
18059 Rostock
Bundesrepublik Deutschland
;
_publ_contact_author_name        'Peter Langer'
_publ_section_title
;
 Synthesis of Highly Functionalized Biaryls by Condensation of
 2-Fluoro-1,3-bis(silyloxy) 1,3-Dienes with 3-Cyanochromones and
 Subsequent Domino "Retro-Michael/Aldol/Fragmentation"
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8315
_journal_page_last               8318
_journal_paper_doi               10.1021/jo1018443
_journal_volume                  75
_journal_year                    2010
_chemical_formula_moiety         'C20 H19 Cl F N O4'
_chemical_formula_sum            'C20 H19 Cl F N O4'
_chemical_formula_weight         391.81
_chemical_name_systematic
;
6-butyl-4-cyano-2-fluoro-3-5-chloro-(2-ethoxycarbonyloxy)-phenole
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_author_name               'Villinger, A.'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 109.443(16)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   21.194(18)
_cell_length_b                   8.813(7)
_cell_length_c                   22.075(19)
_cell_measurement_reflns_used    9981
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      59.322
_cell_measurement_theta_min      6.077
_cell_volume                     3888(6)
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_collection       'Bruker Apex V7.51A'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker Apex Kappa II-CCD-diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_av_sigmaI/netI    0.0497
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            35474
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         3.43
_exptl_absorpt_coefficient_mu    0.231
_exptl_absorpt_correction_T_max  0.9662
_exptl_absorpt_correction_T_min  0.8627
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1632
_exptl_crystal_size_max          0.66
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     508
_refine_ls_number_reflns         8885
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0935
_refine_ls_R_factor_gt           0.0517
_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^)+(0.0872P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1357
_refine_ls_wR_factor_ref         0.1510
_reflns_number_gt                5793
_reflns_number_total             8885
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            jo1018443_si_002_2.cif
_cod_data_source_block           av_mn30
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4025858