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_4106190
_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            'C18 H17 Cl2 N O5'
_chemical_formula_weight         398.23
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_audit_creation_method           SHELXL-97
_cell_angle_alpha                88.98(3)
_cell_angle_beta                 81.05(3)
_cell_angle_gamma                77.28(3)
_cell_formula_units_Z            1
_cell_length_a                   4.9450(10)
_cell_length_b                   6.6101(13)
_cell_length_c                   14.853(3)
_cell_measurement_reflns_used    2863
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.94
_cell_measurement_theta_min      2.78
_cell_volume                     467.75(18)
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0118
_diffrn_reflns_av_sigmaI/netI    0.0238
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
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_diffrn_reflns_limit_k_min       -7
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_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3426
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         1.39
_diffrn_standards_decay_%        1
_exptl_absorpt_coefficient_mu    0.375
_exptl_absorpt_correction_T_max  0.9424
_exptl_absorpt_correction_T_min  0.9153
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1999)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_description       Parallalepiped
_exptl_crystal_F_000             206
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.168
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_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.14(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         2743
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.110
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0321
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0400P)^2^+0.0400P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0774
_refine_ls_wR_factor_ref         0.0785
_reflns_number_gt                2636
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_reflns_threshold_expression     >2sigma(I)
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_cod_data_source_block           nick2
_cod_original_cell_volume        467.77(16)
_cod_database_code               4106190