Crystallization of an Achiral Cyclohexanone Ethylene Ketal in Enantiomorphs and Determination of the Absolute Structure
Sara Graus; Rosa M. Tejedor; Santiago Uriel; José Luis Serrano; Ibon Alkorta; José Elguero; Journal of the American Chemical Society 132 (2010) 7862–7863; doi:10.1021/ja1025062

data_4102524
_publ_contact_author_address
;Departamento de Qu\'imica Organica, Universidad de Zaragoza
C/ Maria de Luna 3 50015 Zaragoza Spain
;
_publ_contact_author_email       suriel@unizar.es
_publ_contact_author_name        'Santiago Uriel'
_publ_contact_author_phone       '+34 976762397'
_publ_section_title
;
 Crystallization of an Achiral Cyclohexanone Ethylene Ketal in
 Enantiomorphs and Determination of the Absolute Structure
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7862
_journal_page_last               7863
_journal_paper_doi               10.1021/ja1025062
_journal_volume                  132
_journal_year                    2010
_chemical_formula_sum            'C16 H22 O4'
_chemical_formula_weight         278.34
_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
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.19 (release 28-02-2008 CrysAlis171 .NET)
(compiled Feb 28 2008,12:10:31)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 94.397(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.4942(2)
_cell_length_b                   7.3340(2)
_cell_length_c                   15.1138(4)
_cell_measurement_reflns_used    4432
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.4940
_cell_measurement_theta_min      3.1325
_cell_volume                     717.73(4)
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.19 (release 28-02-2008 CrysAlis171 .NET)
(compiled Feb 28 2008,12:10:31)
;
_computing_data_collection
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.32.19 (release 28-02-2008 CrysAlis171 .NET)
(compiled Feb 28 2008,12:10:31)
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.19 (release 28-02-2008 CrysAlis171 .NET)
(compiled Feb 28 2008,12:10:31)
;
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.3990
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -43.00   12.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      -21.1177  -77.0000   30.0000    0.0000    0.0000 55

  2 omega   -3.00   49.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       21.5865  -45.0000   90.0000    0.0000    0.0000 52

  3 omega    0.00   55.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       21.5865  -77.0000  300.0000    0.0000    0.0000 55

  4 omega   -3.00   49.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       21.5865  -45.0000    0.0000    0.0000    0.0000 52

  5 omega    0.00   55.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       21.5865  -77.0000  210.0000    0.0000    0.0000 55

  6 omega   20.00   97.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       21.5865    0.0000  150.0000    0.0000    0.0000 77

  7 omega   40.00   94.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       21.5865   77.0000  330.0000    0.0000    0.0000 54

  8 omega   42.00   94.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       21.5865   45.0000  270.0000    0.0000    0.0000 52

  9 omega  -11.00   44.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       21.5865   77.0000  210.0000    0.0000    0.0000 55

 10 omega   45.00   97.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       21.5865    0.0000  240.0000    0.0000    0.0000 52

 11 omega  -96.00   54.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      -21.1177    0.0000   60.0000    0.0000    0.0000 150

 12 omega  -53.00   97.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       21.5865    0.0000  210.0000    0.0000    0.0000 150

 13 omega  -53.00   97.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       21.5865    0.0000  270.0000    0.0000    0.0000 150

 14 omega  -53.00   59.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       21.5865    0.0000  180.0000    0.0000    0.0000 112

;
_diffrn_orient_matrix_UB_11      -0.0195687978
_diffrn_orient_matrix_UB_12      -0.0018944307
_diffrn_orient_matrix_UB_13      0.0456057389
_diffrn_orient_matrix_UB_21      0.1078413279
_diffrn_orient_matrix_UB_22      0.0035378782
_diffrn_orient_matrix_UB_23      0.0119742872
_diffrn_orient_matrix_UB_31      -0.0042791136
_diffrn_orient_matrix_UB_32      0.0967186237
_diffrn_orient_matrix_UB_33      0.0004701636
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0528
_diffrn_reflns_av_sigmaI/netI    0.0545
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13974
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.70
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  1.1173
_exptl_absorpt_correction_T_min  0.9062
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.19 (release 28-02-2008 CrysAlis171 .NET)
(compiled Feb 28 2008,12:10:31)
empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.124
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1.6(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.860
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     269
_refine_ls_number_reflns         2875
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.860
_refine_ls_R_factor_all          0.0650
_refine_ls_R_factor_gt           0.0359
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0339P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0631
_refine_ls_wR_factor_ref         0.0683
_reflns_number_gt                1908
_reflns_number_total             2875
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja1025062_si_001.cif
_cod_data_source_block           Compound(1)
_cod_database_code               4102524