N-heterocyclic carbene catalyzed transformations of 3-halopropenals to the equivalents of beta-acylvinyl anions.
Wu, Yihua; Yao, Weijun; Pan, Lianjie; Zhang, Yiping; Ma, Cheng; Organic letters 12 (2010) 640–643; doi:10.1021/ol902961y

data_1503435
_publ_section_title
;
 N-heterocyclic carbene catalyzed transformations of 3-halopropenals to
 the equivalents of beta-acylvinyl anions.
;
_journal_issue                   3
_journal_name_full               'Organic letters'
_journal_page_first              640
_journal_page_last               643
_journal_paper_doi               10.1021/ol902961y
_journal_volume                  12
_journal_year                    2010
_chemical_formula_moiety         'C17 H19 Br N2 O5'
_chemical_formula_sum            'C17 H19 Br N2 O5'
_chemical_formula_weight         411.25
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                97.369(2)
_cell_angle_beta                 101.399(2)
_cell_angle_gamma                107.244(2)
_cell_formula_units_Z            2
_cell_length_a                   9.5516(6)
_cell_length_b                   9.9896(5)
_cell_length_c                   10.7976(7)
_cell_measurement_reflns_used    5511
_cell_measurement_temperature    296(1)
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      3.2
_cell_volume                     945.15(10)
_computing_cell_refinement       'PROCESS-AUTO  (Rigaku,2006)'
_computing_data_collection       'PROCESS-AUTO  (Rigaku,2006)'
_computing_data_reduction        'CrystalStructure (Rigaku,2007)'
_computing_molecular_graphics    'Ortep3 for windows (Farrugia,1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(1)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rolling anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_sigmaI/netI    0.0417
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8291
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.17
_exptl_absorpt_coefficient_mu    2.203
_exptl_absorpt_correction_T_max  0.5877
_exptl_absorpt_correction_T_min  0.4178
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Higashi, T. (1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       chunk
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.418
_refine_diff_density_min         -0.549
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       0.037(2)
_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   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         3714
_refine_ls_number_restraints     54
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0899
_refine_ls_R_factor_gt           0.0390
_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^)+(0.0350P)^2^+1.6000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0841
_refine_ls_wR_factor_ref         0.1275
_reflns_number_gt                2152
_reflns_number_total             3714
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol902961y_si_003.cif
_cod_data_source_block           6d
_cod_database_code               1503435