Synthesis, Structure, and E-Z Isomerization of β-(Hetero)aryl-α,β-enals
Patricia Martínez-Bescos; Fernando Cagide-Fagín; Luis F. Roa; Juan Carlos Ortiz-Lara; Krzysztof Kierus; Lidia Ozores-Viturro; Marta Fernández-González; Ricardo Alonso; Journal of Organic Chemistry 73 (2008) 3745–3753; doi:10.1021/jo702731b

data_4023403
_publ_contact_author_address
'Department of Organic Chemistry, USC, 15782 Santiago de Compostela, Spain'
_publ_contact_author_email       qoraa@usc.es
_publ_contact_author_fax         +34981595012
_publ_contact_author_name        'Ricardo Alonso Alonso'
_publ_contact_author_phone       +34981547085
_publ_section_title
;
 Synthesis, Structure, and E-Z Isomerization of
 \b-(Hetero)aryl-\a,\b-enals
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3745
_journal_page_last               3753
_journal_paper_doi               10.1021/jo702731b
_journal_volume                  73
_journal_year                    2008
_chemical_absolute_configuration syn
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C7 H7 N1 O4'
_chemical_formula_sum            'C7 H7 N O4'
_chemical_formula_weight         169.14
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      9
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 100.230(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.24040(10)
_cell_length_b                   22.1197(6)
_cell_length_c                   7.9235(2)
_cell_measurement_reflns_used    1882
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.28
_cell_measurement_theta_min      3.19
_cell_measurement_wavelength     0.71073
_cell_volume                     731.38(3)
_computing_cell_refinement       'Bruker APEXII'
_computing_data_collection       'Bruker APEXII'
_computing_data_reduction        'Bruker XPREP'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'BRUKER APPEX-II CCD'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5069
_diffrn_reflns_theta_full        26.38
_diffrn_reflns_theta_max         26.38
_diffrn_reflns_theta_min         1.84
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.817811
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'BRUKER SADABS'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.536
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.2(11)
_refine_ls_extinction_coef       0.0009(1)
_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   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     141
_refine_ls_number_reflns         1497
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0316
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0304P)^2^+0.2150P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0656
_refine_ls_wR_factor_ref         0.0681
_reflns_number_gt                1335
_reflns_number_total             1497
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo702731b-File005.cif
_cod_data_source_block           New_Global_Publ_Block
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               4023403