Oxiranyl Anion-Mediated Synthesis of Highly Enantiomerically Enriched Styrene Oxide Derivatives
Capriati, Vito; Florio, Saverio; Luisi, Renzo; Salomone, Antonio; Organic Letters 4 (2002) 2445–; doi:10.1021/ol026212d

data_1507473
_publ_contact_author
;Prof. Saverio Florio

;
_publ_section_title
;
 Oxiranyl Anion-Mediated Synthesis of Highly Enantiomerically Enriched
 Styrene Oxide Derivatives
;
_journal_issue                   14
_journal_name_full               'Organic Letters'
_journal_page_first              2445
_journal_paper_doi               10.1021/ol026212d
_journal_volume                  4
_journal_year                    2002
_chemical_formula_sum            'C15 H14 O2'
_chemical_formula_weight         226.27
_chemical_melting_point          104-107&#x00A1;C
_chemical_name_systematic
;
1,2-diphenyl-2,3-epoxypropan-1-ol
;
_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                90.000(10)
_cell_angle_beta                 105.779(2)
_cell_angle_gamma                90.000(10)
_cell_formula_units_Z            2
_cell_length_a                   8.6090(3)
_cell_length_b                   5.8100(2)
_cell_length_c                   12.6280(5)
_cell_measurement_reflns_used    8492
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.3
_cell_measurement_theta_min      2
_cell_volume                     607.83(4)
_computing_data_collection       'KappaCCD   (Nonius, 1998)  '
_computing_data_reduction
'Denzo and Scalepak (Otwinowski & Minor, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.927
_diffrn_measured_fraction_theta_max 0.927
_diffrn_measurement_device       KappaCCD
_diffrn_measurement_method       phi-scan
_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  0.026
_diffrn_reflns_av_sigmaI/netI    0.0215
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8492
_diffrn_reflns_theta_full        26.35
_diffrn_reflns_theta_max         26.35
_diffrn_reflns_theta_min         1.68
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             236
_exptl_crystal_preparation       n-hexane
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.094
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(2)
_refine_ls_extinction_coef       3.6(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.235
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         1265
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.234
_refine_ls_R_factor_all          0.0723
_refine_ls_R_factor_gt           0.0662
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1250P)^2^+0.0152P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1602
_refine_ls_wR_factor_ref         0.1727
_reflns_number_gt                1187
_reflns_number_total             1265
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol026212d_s2.cif
_cod_data_source_block           shelxl
_cod_original_sg_symbol_H-M      P21
_cod_database_code               1507473