Enantioselective enol lactone synthesis under double catalytic conditions.
Itoh, Kennosuke; Hasegawa, Masayuki; Tanaka, Junji; Kanemasa, Shuji; Organic letters 7 (2005) 979–981; doi:10.1021/ol047872g

data_1506500
_publ_section_title
;
 Enantioselective enol lactone synthesis under double catalytic
 conditions.
;
_journal_issue                   6
_journal_name_full               'Organic letters'
_journal_page_first              979
_journal_page_last               981
_journal_paper_doi               10.1021/ol047872g
_journal_volume                  7
_journal_year                    2005
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H17 Br O3 '
_chemical_formula_sum            'C17 H17 Br O3'
_chemical_formula_weight         349.22
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_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'
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_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.4250(9)
_cell_length_b                   21.493(1)
_cell_length_c                   5.9427(4)
_cell_measurement_reflns_used    20907
_cell_measurement_temperature    296.2
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1.9
_cell_volume                     1587.00(17)
_computing_cell_refinement       'MSC/AFC Diffractometer Control'
_computing_data_collection       'MSC/AFC Diffractometer Control'
_computing_data_reduction
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 teXsan for Windows version 1.06 (MSC, 1997-1999)
;
_computing_publication_material
;
 teXsan for Windows version 1.06 (MSC, 1997-1999)
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_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution
;
SHELX97 (Sheldrick, 1997)
;
_diffrn_ambient_temperature      296.2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       \w/2\q
_diffrn_orient_matrix_UB_11      0.04542
_diffrn_orient_matrix_UB_12      0.00184
_diffrn_orient_matrix_UB_13      -0.13876
_diffrn_orient_matrix_UB_21      -0.02585
_diffrn_orient_matrix_UB_22      -0.04233
_diffrn_orient_matrix_UB_23      -0.04431
_diffrn_orient_matrix_UB_31      -0.06121
_diffrn_orient_matrix_UB_32      0.01924
_diffrn_orient_matrix_UB_33      -0.08425
_diffrn_radiation_detector       'Imaging Plate'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.00000
_diffrn_reflns_av_sigmaI/netI    0.103
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
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_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            3658
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         1.89
_diffrn_standards_decay_%        0.00
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.597
_exptl_absorpt_correction_T_max  0.5096
_exptl_absorpt_correction_T_min  0.3567
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_density_meas      ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             712.00
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         1.169
_refine_diff_density_min         -0.506
_refine_diff_density_rms         0.105
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(2)
_refine_ls_extinction_coef       0.049(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   0.940
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3633
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.940
_refine_ls_R_factor_all          0.0722
_refine_ls_R_factor_gt           0.0513
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0838P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1304
_refine_ls_wR_factor_ref         0.1466
_reflns_number_gt                2457
_reflns_number_total             3633
_reflns_threshold_expression     I>3.00\s(I)
_cod_data_source_file            ol047872gsi20041223_085129.cif
_cod_data_source_block           '_ITO920___________________'
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        1586.98(18)
_cod_original_sg_symbol_Hall     ' P 2ac 2ab '
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_original_formula_sum        'C17 H17 Br O3 '
_cod_database_code               1506500