Kinetic resolution of racemic 2,3-allenoates by organocatalytic asymmetric 1,3-dipolar cycloaddition.
Yu, Jie; Chen, Wei-Jie; Gong, Liu-Zhu; Organic letters 12 (2010) 4050–4053; doi:10.1021/ol101544c

data_1503151
_publ_section_title
;
 Kinetic resolution of racemic 2,3-allenoates by organocatalytic
 asymmetric 1,3-dipolar cycloaddition.
;
_journal_issue                   18
_journal_name_full               'Organic letters'
_journal_page_first              4050
_journal_page_last               4053
_journal_paper_doi               10.1021/ol101544c
_journal_volume                  12
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_formula_sum            'C18 H15 Br O2'
_chemical_formula_weight         343.21
_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                 107.156(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.5681(3)
_cell_length_b                   8.12920(10)
_cell_length_c                   15.1521(3)
_cell_measurement_reflns_used    9565
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      62.5552
_cell_measurement_theta_min      3.0477
_cell_volume                     1596.88(5)
_computing_cell_refinement       'CrysAlisPro (Oxford Diffraction Ltd.)'
_computing_data_collection       'CrysAlisPro (Oxford Diffraction Ltd.)'
_computing_data_reduction        'CrysAlisPro (Oxford Diffraction Ltd.)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      291(2)
_diffrn_detector_area_resol_mean 15.9149
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Gemini S Ultra, Oxford Diffraction'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_sigmaI/netI    0.0189
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14999
_diffrn_reflns_theta_full        62.74
_diffrn_reflns_theta_max         62.74
_diffrn_reflns_theta_min         3.05
_exptl_absorpt_coefficient_mu    3.516
_exptl_absorpt_correction_T_max  0.3642
_exptl_absorpt_correction_T_min  0.3337
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET)
(compiled Feb 27 2009,15:38:38)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.36
_refine_diff_density_max         0.485
_refine_diff_density_min         -0.480
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     381
_refine_ls_number_reflns         4914
_refine_ls_number_restraints     64
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0639
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0850P)^2^+1.6027P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1700
_refine_ls_wR_factor_ref         0.1756
_reflns_number_gt                4202
_reflns_number_total             4914
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol101544c_si_002.cif
_cod_data_source_block           100507
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1503151