An Enantioselective Approach toward 3,4-Dihydroisocoumarin through the Bromocyclization of Styrene-type Carboxylic Acids
Jie Chen; Ling Zhou; Chong Kiat Tan; Ying-Yeung Yeung; Journal of Organic Chemistry 77 (2012) 999–1009; doi:10.1021/jo202221c

data_4026895
_publ_section_title
;
 An Enantioselective Approach toward 3,4-Dihydroisocoumarin through the
 Bromocyclization of Styrene-type Carboxylic Acids
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              999
_journal_page_last               1009
_journal_paper_doi               10.1021/jo202221c
_journal_volume                  77
_journal_year                    2012
_chemical_formula_sum            'C19 H13 Br O2'
_chemical_formula_weight         353.20
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 101.539(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.3746(10)
_cell_length_b                   5.6910(7)
_cell_length_c                   15.6697(18)
_cell_measurement_reflns_used    864
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.35
_cell_measurement_theta_min      2.48
_cell_volume                     731.72(15)
_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  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0235
_diffrn_reflns_av_sigmaI/netI    0.0623
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            5083
_diffrn_reflns_theta_full        27.41
_diffrn_reflns_theta_max         27.41
_diffrn_reflns_theta_min         2.48
_exptl_absorpt_coefficient_mu    2.813
_exptl_absorpt_correction_T_max  0.3336
_exptl_absorpt_correction_T_min  0.3018
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2001)'
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.603
_exptl_crystal_density_meas      ?
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.56
_exptl_crystal_size_min          0.50
_refine_diff_density_max         0.932
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.080
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.005(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3137
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0326
_refine_ls_R_factor_gt           0.0308
_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^)+(0.0235P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0734
_refine_ls_wR_factor_ref         0.0750
_reflns_number_gt                2956
_reflns_number_total             3137
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo202221c_si_001.cif
_cod_data_source_block           b008
_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 
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_cod_database_code               4026895