Asymmetric Synthesis of 2-Substituted Oxetan-3-ones via Metalated SAMP/RAMP Hydrazones
Joanna V. Geden; Benjamin O. Beasley; Guy J. Clarkson; Michael Shipman; Journal of Organic Chemistry 78 (2013) 12243–12250; doi:10.1021/jo4020485

data_4028820
_publ_section_title
;
 Asymmetric Synthesis of 2-Substituted Oxetan-3-ones via Metalated
 SAMP/RAMP Hydrazones
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              12243
_journal_page_last               12250
_journal_paper_doi               10.1021/jo4020485
_journal_volume                  78
_journal_year                    2013
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C23 H24 N2 O3, C5 H12'
_chemical_formula_sum            'C28 H36 N2 O3'
_chemical_formula_weight         448.59
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           154
_symmetry_cell_setting           hexagonal
_symmetry_space_group_name_Hall  'P 32 2"'
_symmetry_space_group_name_H-M   'P 32 2 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                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            18
_cell_length_a                   17.3834(3)
_cell_length_b                   17.3834(3)
_cell_length_c                   48.1688(14)
_cell_measurement_reflns_used    9695
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      76.83
_cell_measurement_theta_min      3.07
_cell_volume                     12605.7(5)
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd'
_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997)'
_computing_publication_material  'SHELXTL (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.2833
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Oxford Diffraction Gemini R'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) x-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0484
_diffrn_reflns_av_sigmaI/netI    0.0453
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       51
_diffrn_reflns_limit_l_min       -60
_diffrn_reflns_number            53087
_diffrn_reflns_theta_full        70.00
_diffrn_reflns_theta_max         77.00
_diffrn_reflns_theta_min         3.08
_diffrn_standards_decay_%        nil
_exptl_absorpt_coefficient_mu    0.542
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.68
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSPACK(CrysAlis, Oxford Diffraction)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.064
_exptl_crystal_description       block
_exptl_crystal_F_000             4356
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.10
_platon_squeeze_details
;

The unit cell contains 18 pentane molecules which have been 
treated as a diffuse contribution to the overall scattering without specific 
atom positions by SQUEEZE/PLATON.

Volume of pentane roughly 250 Angstroms cubed.
Electron count of pentane 42 electrons

The new fcf (bb6-sr.fcf) is appended to the end of the cif file.
;
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881, 7723 Friedel pairs '
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     775
_refine_ls_number_reflns         17317
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0942
_refine_ls_R_factor_gt           0.0755
_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^)+(0.1288P)^2^+0.0439P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2105
_refine_ls_wR_factor_ref         0.2257
_reflns_number_gt                12197
_reflns_number_total             17317
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo4020485_si_002.cif
_cod_data_source_block           bb6-sr
_cod_original_cell_volume        12605.6(5)
_cod_database_code               4028820
_cod_database_fobs_code          4028820