Enantioselective Desymmetrization of Cyclopropenes by Hydroacylation
Diem H. T. Phan; Kevin G. M. Kou; Vy M. Dong; Journal of the American Chemical Society 132 (2010) 16354–16355; doi:10.1021/ja107738a

data_4103555
_publ_section_title
;
 Enantioselective Desymmetrization of Cyclopropenes by Hydroacylation
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              16354
_journal_page_last               16355
_journal_paper_doi               10.1021/ja107738a
_journal_volume                  132
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H15 Cl O2'
_chemical_formula_sum            'C17 H15 Cl O2'
_chemical_formula_weight         286.74
_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                 90.022(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   5.7293(3)
_cell_length_b                   22.6204(15)
_cell_length_c                   22.0844(11)
_cell_measurement_reflns_used    16905
_cell_measurement_temperature    150(1)
_cell_measurement_theta_max      25.4
_cell_measurement_theta_min      2.6
_cell_volume                     2862.1(3)
_computing_cell_refinement       'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Nonius B.V., 1997-2002)'
_computing_data_reduction        Denzo-SMN
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL V6.1'
_computing_structure_refinement  'SHELXTL V6.1 (Sheldrick, 2008)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150(1)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       '\f scans and \w scans with \k offsets'
_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  0.0798
_diffrn_reflns_av_sigmaI/netI    0.1053
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            16905
_diffrn_reflns_theta_full        25.04
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_min         2.58
_exptl_absorpt_coefficient_mu    0.265
_exptl_absorpt_correction_T_max  0.975
_exptl_absorpt_correction_T_min  0.771
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.07(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     726
_refine_ls_number_reflns         8341
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.1229
_refine_ls_R_factor_gt           0.0644
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0845P)^2^+0.6360P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1469
_refine_ls_wR_factor_ref         0.1803
_reflns_number_gt                5247
_reflns_number_total             8341
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ja107738a_si_005.cif
_cod_data_source_block           k10211a
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4103555