direct Organocatalytic Asymmetric α-Chlorination of Aldehydes
Nis Halland; Alan Braunton; Stephan Bachmann; Mauro Marigo; Karl Anker Jørgensen; Journal of the American Chemical Society 126 (2004) 4790–4791; doi:10.1021/ja049231m

data_4112462
_publ_contact_author
'Rita Hazell, Chemistry department, Aarhus University, DK8000 Aarhus C'
_publ_section_title
;
 direct Organocatalytic Asymmetric \a-Chlorination of Aldehydes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4790
_journal_page_last               4791
_journal_paper_doi               10.1021/ja049231m
_journal_volume                  126
_journal_year                    2004
_chemical_formula_moiety         'C6 H13 Cl O'
_chemical_formula_sum            'C6 H13 Cl O'
_chemical_formula_weight         136.61
_chemical_name_systematic
;                                   
(R)-2-Chloro-3,3dimethyl-butan-1-ol 
;
_space_group_IT_number           145
_symmetry_cell_setting           hexagonal
_symmetry_space_group_name_Hall  'P 32'
_symmetry_space_group_name_H-M   'P 32'
_atom_type_scat_source           IntTabIV
_cell_angle_alpha                90.000
_cell_angle_beta                 90.000
_cell_angle_gamma                120.000
_cell_formula_units_Z            9
_cell_length_a                   17.826(2)
_cell_length_b                   17.826(2)
_cell_length_c                   6.193(2)
_cell_measurement_reflns_used    5237
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.20
_cell_measurement_theta_min      2.28
_cell_volume                     1704.3(6)
_computing_cell_refinement       'SAINT (Siemens, 1995)'
_computing_data_collection       'SMART (Siemens, 1995)'
_computing_data_reduction        'SAINT (Siemens, 1995)'
_computing_molecular_graphics
;                                   
      ORTEP-III (Burnett & Johnson,  1996), KRYSTAL                     
;
_computing_publication_material  KRYSTAL
_computing_structure_refinement  'modified ORFLS(1962), KRYSTAL'
_computing_structure_solution
;                                   
     SIR97 (Altomare et al., 1997 ), KRYSTAL                            
;
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Siemens SMART CCD diffractometer'
_diffrn_measurement_method       '\w rotation scans with narrow frames'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'x-ray tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.17
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       .23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            20015
_diffrn_reflns_reduction_process 20015
_diffrn_reflns_theta_full        28.2
_diffrn_reflns_theta_max         28.20
_diffrn_reflns_theta_min         2.28
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.4153
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.198
_exptl_crystal_description       plate
_exptl_crystal_F_000             666
_exptl_crystal_size_max          0.64
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_refine_diff_density_max         2.3(2)
_refine_diff_density_min         -1.2(2)
_refine_ls_abs_structure_details
;Least squares refinement included a parameter 
according to Rogers (1981) refined against all
3737 significant reflections, including 1595
Bijvoet pairs. The indication from this - although
weak supports the chirality found in other ways.
;
_refine_ls_abs_structure_Rogers  0.64(33)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.99
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     214
_refine_ls_number_reflns         3737
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.103
_refine_ls_shift/su_max          0.013
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;                                   
w= 1/{[\s~cs~(F^2^)+B+(1+A)F^2^]^1/2^- |F|}^2^ 
where A = 0.06   and B = 0.5               
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.128
_reflns_number_gt                3737
_reflns_number_total             5581
_reflns_threshold_expression     I>3\s(I)
_cod_data_source_file            ja049231msi20040212_113830.cif
_cod_data_source_block           Cpd4b
_cod_database_code               4112462