A stereoselective intramolecular halo-etherification of chiral enamides in the synthesis of halogenated cyclic ethers.
Ko, Changhong; Hsung, Richard P.; Al-Rashid, Ziyad F; Feltenberger, John B.; Lu, Ting; Yang, Jin-Haek; Wei, Yonggang; Zificsak, Craig A.; Organic letters 9 (2007) 4459–4462; doi:10.1021/ol701768n

data_1505545
_publ_section_title
;
 A stereoselective intramolecular halo-etherification of chiral enamides
 in the synthesis of halogenated cyclic ethers.
;
_journal_issue                   22
_journal_name_full               'Organic letters'
_journal_page_first              4459
_journal_page_last               4462
_journal_paper_doi               10.1021/ol701768n
_journal_volume                  9
_journal_year                    2007
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C13 H14 Br N O3'
_chemical_formula_sum            'C13 H14 Br N O3'
_chemical_formula_weight         312.16
_chemical_name_common            07112a
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 115.333(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   20.682(4)
_cell_length_b                   5.9165(10)
_cell_length_c                   11.670(2)
_cell_measurement_reflns_used    1656
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.67
_cell_measurement_theta_min      3.48
_cell_volume                     1290.7(4)
_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    SIR-2002
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'CCD area detector'
_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  0.0338
_diffrn_reflns_av_sigmaI/netI    0.0645
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            6044
_diffrn_reflns_theta_full        27.06
_diffrn_reflns_theta_max         27.06
_diffrn_reflns_theta_min         1.93
_exptl_absorpt_coefficient_mu    3.185
_exptl_absorpt_correction_T_max  0.6823
_exptl_absorpt_correction_T_min  0.3283
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (G. Sheldrick, 2003)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.607
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.794
_refine_diff_density_min         -0.486
_refine_diff_density_rms         0.077
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.021(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.977
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2744
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.977
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0352
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0340P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0791
_refine_ls_wR_factor_ref         0.0830
_reflns_number_gt                2344
_reflns_number_total             2744
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol701768n-file004.cif
_cod_data_source_block           07112a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1290.6(4)
_cod_original_sg_symbol_H-M      'C2   '
_cod_database_code               1505545