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_4028822
_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     direct
_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                 91.672(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.2592(2)
_cell_length_b                   5.45466(16)
_cell_length_c                   38.5981(10)
_cell_measurement_reflns_used    3530
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      75.0254
_cell_measurement_theta_min      3.4338
_cell_volume                     1738.15(8)
_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
;
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
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      150.15
_diffrn_detector_area_resol_mean 10.2833
_diffrn_measured_fraction_theta_full 0.9954
_diffrn_measured_fraction_theta_max 0.9755
_diffrn_measurement_details
;
  1 omega   56.00   99.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000 -178.0000  -30.0000 43

  2 omega    8.00   42.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   82.0000  -36.0000 34

  3 omega   53.00   78.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000 -178.0000    0.0000 25

  4 omega   22.00   48.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000   30.0000 26

  5 omega    4.00   29.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000 -106.0000  -64.0000 25

  6 omega -125.00  -77.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -59.6766  -82.0000   22.0000 48

  7 omega -125.00  -73.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -59.6766  -61.0000  -60.0000 52

  8 omega  -60.00  -22.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -59.6766  -61.0000  -60.0000 38

  9 omega   96.00  150.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       59.6766  125.0000  -30.0000 54

 10 omega   95.00  154.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       59.6766  125.0000 -120.0000 59

 11 omega   95.00  150.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       59.6766  125.0000   30.0000 55

 12 omega  -93.00  -32.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      -73.5000  178.0000   60.0000 61

 13 omega   25.00   52.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      119.3533  -38.0000    0.0000 27

 14 omega   86.00  148.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      119.3533  178.0000   60.0000 62

 15 omega   23.00   92.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      119.3533  -25.0000 -120.0000 69

 16 omega  109.00  178.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      119.3533  111.0000 -120.0000 69

 17 omega   98.00  148.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      119.3533   82.0000  -22.0000 50

 18 omega   29.00   80.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      119.3533  -50.0000 -150.0000 51

 19 omega  102.00  168.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      119.3533  111.0000  -90.0000 66

 20 omega   24.00   97.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      119.3533 -111.0000 -120.0000 73

 21 omega   75.00  141.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      119.3533  178.0000 -180.0000 66
;
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0687064000
_diffrn_orient_matrix_UB_12      0.0292630000
_diffrn_orient_matrix_UB_13      0.0373065000
_diffrn_orient_matrix_UB_21      0.0795499000
_diffrn_orient_matrix_UB_22      0.2439830000
_diffrn_orient_matrix_UB_23      -0.0101988000
_diffrn_orient_matrix_UB_31      -0.1540914000
_diffrn_orient_matrix_UB_32      0.1392259000
_diffrn_orient_matrix_UB_33      0.0099925000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0180
_diffrn_reflns_av_unetI/netI     0.0194
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_number            5880
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.204
_diffrn_reflns_theta_min         4.584
_diffrn_source                   'Enhance (Cu) x-ray Source'
_exptl_absorpt_coefficient_mu    0.837
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61454
_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    1.362
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         3497
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0449
_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^)+(0.0572P)^2^+0.8286P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1189
_refine_ls_wR_factor_ref         0.1202
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3334
_reflns_number_total             3497
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo4020485_si_004.cif
_cod_data_source_block           jg2
_cod_database_code               4028822
_cod_database_fobs_code          4028822
_chemical_oxdiff_formula         'C20 H20 N2 O2'
_reflns_odcompleteness_completeness 99.54
_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, H21 of C21, H8 of C8, H9 of C9, H22 of C22, H20 of C20,
  H7 of C7, H4 of C4, H18 of C18, H15 of C15, H10 of C10, H11 of C11, H19 of C19
 At 1.5 times of:
  H5 of C5, H16 of C16
2. Restrained distances
 O5-H5A
 0.87 with sigma of 0.02
 H5A-H5
 2.1 with sigma of 0.04
3.a Ternary CH refined with riding coordinates:
 C4(H4), C5(H5), C15(H15), C16(H16)
3.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C13(H13A,H13B)
3.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C18(H18), C19(H19), C20(H20),
 C21(H21), C22(H22)
;
_shelxl_version_number           2013-2