Enantioselective Dichlorination of Allylic Alcohols
K. C. Nicolaou; Nicholas L. Simmons; Yongcheng Ying; Philipp M. Heretsch; Jason S. Chen; Journal of the American Chemical Society 133 (2011) 8134–8137; doi:10.1021/ja202555m

data_4106189
_publ_section_title
;
 Enantioselective Dichlorination of Allylic Alcohols
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8134
_journal_page_last               8137
_journal_paper_doi               10.1021/ja202555m
_journal_volume                  133
_journal_year                    2011
_chemical_formula_sum            'C16 H12 Cl3 N O4'
_chemical_formula_weight         388.62
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
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_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                85.06(3)
_cell_angle_beta                 77.13(3)
_cell_angle_gamma                87.58(3)
_cell_formula_units_Z            2
_cell_length_a                   7.2930(15)
_cell_length_b                   10.030(2)
_cell_length_c                   12.207(2)
_cell_measurement_reflns_used    3339
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.27
_cell_measurement_theta_min      2.56
_cell_volume                     867.0(3)
_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, 1997)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_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  0.0161
_diffrn_reflns_av_sigmaI/netI    0.0356
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
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_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6299
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         1.72
_diffrn_standards_decay_%        1
_exptl_absorpt_coefficient_mu    0.548
_exptl_absorpt_correction_T_max  0.9078
_exptl_absorpt_correction_T_min  0.8485
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1999)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_description       Parallalepiped
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.074
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.07(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     433
_refine_ls_number_reflns         5030
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.110
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0614
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0.009
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0900P)^2^+0.5500P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1752
_refine_ls_wR_factor_ref         0.1826
_reflns_number_gt                4300
_reflns_number_total             5030
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja202555m_si_002.cif
_cod_data_source_block           nick
_cod_original_cell_volume        867.1(3)
_cod_database_code               4106189