Gamma-hydroxynitrile alkylations: electrophile-dependent stereoselectivity.
Mycka, Robert J.; Steward, Omar W.; Fleming, Fraser F.; Organic letters 12 (2010) 3030–3033; doi:10.1021/ol101030r

data_1503442
_publ_section_title
;
 Gamma-hydroxynitrile alkylations: electrophile-dependent
 stereoselectivity.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              3030
_journal_page_last               3033
_journal_paper_doi               10.1021/ol101030r
_journal_volume                  12
_journal_year                    2010
_chemical_formula_moiety         'C16 H23 N O2'
_chemical_formula_sum            'C16 H23 N O2'
_chemical_formula_weight         261.35
_chemical_melting_point          428.5(15)
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.364(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.1272(3)
_cell_length_b                   11.7615(6)
_cell_length_c                   21.1408(12)
_cell_measurement_reflns_used    11908
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.26
_cell_measurement_theta_min      2.40
_cell_volume                     1523.48(14)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_structure_refinement  'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker Smart ApexII'
_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  0.1172
_diffrn_reflns_av_sigmaI/netI    0.0591
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            11908
_diffrn_reflns_theta_full        21.26
_diffrn_reflns_theta_max         21.26
_diffrn_reflns_theta_min         1.93
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         1690
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.9926
_exptl_absorpt_correction_T_min  0.9709
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS(Sheldrick 2002)'
_exptl_crystal_colour            clear
_exptl_crystal_density_diffrn    1.139
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.114
_refine_diff_density_rms         0.031
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.801
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         1690
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.801
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0419
_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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1129
_refine_ls_wR_factor_ref         0.1259
_reflns_number_gt                1201
_reflns_number_total             1690
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol101030r_si_001.cif
_cod_data_source_block           Retention
_cod_depositor_comments
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The following automatic conversions were performed:

'_chemical_melting_point' value '427-430K' was changed to '428.5(15)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1503442