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_4028823
_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_formula_moiety         'C10 H10 O3'
_chemical_formula_sum            'C10 H10 O3'
_chemical_formula_weight         178.18
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2013-06-09
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_cell_angle_alpha                90
_cell_angle_beta                 100.809(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.91473(14)
_cell_length_b                   17.3076(5)
_cell_length_c                   8.6214(2)
_cell_measurement_reflns_used    2315
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      77.2572
_cell_measurement_theta_min      5.1067
_cell_volume                     866.91(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_diffrn_ambient_temperature      150.15
_diffrn_detector_area_resol_mean 10.2833
_diffrn_measured_fraction_theta_full 0.9994
_diffrn_measured_fraction_theta_max 0.9942
_diffrn_measurement_details
;
  1 omega -118.00   -7.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.6896  -77.0000   30.0000 111

  2 omega  -46.00   15.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.6896   57.0000  -30.0000 61

  3 omega -123.00  -80.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      -55.5000 -111.0000  -30.0000 43

  4 omega   36.00   91.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -30.0000  -30.0000 55

  5 omega   57.00   90.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -30.0000 -180.0000 33

  6 omega   38.00   85.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -30.0000   60.0000 47

  7 omega   75.00  103.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000 -111.0000 -150.0000 28

  8 omega   45.00   98.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000 -111.0000  -30.0000 53

  9 omega   60.00  114.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000 -111.0000  120.0000 54

 10 omega   37.00   73.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -30.0000   30.0000 36

 11 omega   57.00   89.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -30.0000   90.0000 32

 12 omega   44.00   71.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000 -111.0000 -150.0000 27

 13 omega   81.00  109.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -94.0000    0.0000 28

 14 omega   46.00   98.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -45.0000  150.0000 52
;
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0622035000
_diffrn_orient_matrix_UB_12      0.0864711000
_diffrn_orient_matrix_UB_13      0.0168800000
_diffrn_orient_matrix_UB_21      0.0016340000
_diffrn_orient_matrix_UB_22      -0.0046895000
_diffrn_orient_matrix_UB_23      0.1787006000
_diffrn_orient_matrix_UB_31      0.2576142000
_diffrn_orient_matrix_UB_32      -0.0206859000
_diffrn_orient_matrix_UB_33      0.0298786000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0167
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3304
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.469
_diffrn_reflns_theta_min         5.111
_diffrn_source                   'Enhance (Cu) x-ray Source'
_exptl_absorpt_coefficient_mu    0.839
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56809
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     121
_refine_ls_number_reflns         1792
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0389
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0620P)^2^+0.1740P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1079
_refine_ls_wR_factor_ref         0.1103
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1662
_reflns_number_total             1792
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo4020485_si_005.cif
_cod_data_source_block           jg3
_cod_database_code               4028823
_cod_database_fobs_code          4028823
_chemical_oxdiff_formula         'C20 H20 N2 O2'
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.95
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, H9 of C9, H7 of C7, H10 of C10, H11 of C11, H4 of C4, H8
  of C8
 At 1.5 times of:
  H5 of C5, H5A of C11
2.a Ternary CH refined with riding coordinates:
 C4(H4), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C11(H11)
;
_shelxl_version_number           2013-2