The Use of Br/Cl to Promote Regioselective Gold-Catalyzed Rearrangement of Propargylic Carboxylates: Efficient Synthesis of (1Z, 3E)-1-Bromo/Chloro-2-Carboxy-1,3-Dienes from Terminally Halogenated Propargyl Carboxylates
Yanzhao Wang; Biao Lu; Liming Zhang; Chem.Commun. 46 (2010) 9179–; doi:10.1039/c0cc03669b

data_7105734
_publ_section_title
;
 The Use of Br/Cl to Promote Regioselective Gold-Catalyzed Rearrangement
 of Propargylic Carboxylates: Efficient Synthesis of (1Z,
 3E)-1-Bromo/Chloro-2-Carboxy-1,3-Dienes from Terminally Halogenated
 Propargyl Carboxylates
;
_journal_name_full               Chem.Commun.
_journal_page_first              9179
_journal_paper_doi               10.1039/c0cc03669b
_journal_volume                  46
_journal_year                    2010
_chemical_formula_sum            'C18 H18 Br N O4'
_chemical_formula_weight         392.24
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 100.544(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   31.963(4)
_cell_length_b                   5.3557(7)
_cell_length_c                   20.129(3)
_cell_measurement_temperature    150(2)
_cell_volume                     3387.6(8)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'Omega scan'
_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  0.0372
_diffrn_reflns_av_sigmaI/netI    0.0340
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            12990
_diffrn_reflns_theta_full        26.42
_diffrn_reflns_theta_max         26.42
_diffrn_reflns_theta_min         1.30
_exptl_absorpt_coefficient_mu    2.448
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.5
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1600
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.452
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.112
_refine_ls_extinction_coef       0.0037(3)
_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   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3428
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0285
_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^)+(0.0571P)^2^+0.6337P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0784
_refine_ls_wR_factor_ref         0.0929
_reflns_number_gt                2892
_reflns_number_total             3428
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            C0CC03669B.TXT
_cod_data_source_block           zm
_cod_depositor_comments
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The following automatic conversions were performed:
'_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_enum 1527 2010-12-29 10:47:43Z saulius 
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_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7105734