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_4025857
_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_email       peter.langer@uni-rostock.de
_publ_contact_author_fax         '+49 (0)381/498-6410'
_publ_contact_author_name        'Peter Langer'
_publ_contact_author_phone       '+49 (0)381/498-6412'
_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_absolute_configuration unk
_chemical_formula_moiety         'C16 H11 F2 N O4'
_chemical_formula_sum            'C16 H11 F2 N O4'
_chemical_formula_weight         319.26
_chemical_name_systematic
; 
Ethyl 2,7-difluoro-2-(5-oxo-5H-chromeno[2,3-b]pyridin-2-yl)acetate 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_author_name               'Reinke, H., Villinger, A.'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.7205(3)
_cell_length_b                   11.9607(7)
_cell_length_c                   24.1144(12)
_cell_measurement_reflns_used    3647
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      35.04
_cell_measurement_theta_min      3.05
_cell_volume                     1361.51(14)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      103(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0941
_diffrn_reflns_av_sigmaI/netI    0.0852
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            13914
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         2.40
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_T_max  0.9922
_exptl_absorpt_correction_T_min  0.9283
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker (2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.558
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'fragment of prism'
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2302
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.1035
_refine_ls_R_factor_gt           0.0654
_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^)+(0.0531P)^2^+0.2426P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1044
_refine_ls_wR_factor_ref         0.1132
_reflns_number_gt                1657
_reflns_number_total             2302
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo1018443_si_002_1.cif
_cod_data_source_block           ma233_(5p)
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to the built-in table from CIF Core
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_database_code               4025857