Total Synthesis of Purported Cephalosporolides H and I, Penisporolide B, and Their Stereoisomers.
Wang, Jian; Tong, Rongbiao; The Journal of organic chemistry 81 (2016) 4325–4339; doi:10.1021/acs.joc.6b00788

data_4036884
_publ_section_title
;
 Total Synthesis of Purported Cephalosporolides H and I, Penisporolide B,
 and Their Stereoisomers.
;
_journal_issue                   10
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4325
_journal_page_last               4339
_journal_paper_doi               10.1021/acs.joc.6b00788
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C12 H20 O5'
_chemical_formula_sum            'C12 H20 O5'
_chemical_formula_weight         244.28
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-03-10
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   16.80683(18)
_cell_length_b                   14.18677(16)
_cell_length_c                   10.38483(11)
_cell_measurement_reflns_used    7301
_cell_measurement_temperature    99.9(5)
_cell_measurement_theta_max      75.4220
_cell_measurement_theta_min      5.2570
_cell_volume                     2476.10(5)
_computing_cell_refinement
'CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01)'
_computing_data_collection
'CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01)'
_computing_data_reduction
'CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3587
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details
;
  1 omega   36.00  108.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -94.0000 -120.0000 72

  2 omega  -49.00   35.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8203   37.0000   30.0000 84

  3 omega  -46.00   32.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8203   37.0000 -180.0000 78

  4 omega  -96.00   -5.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8203  125.0000   30.0000 91

  5 omega -113.00  -11.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8203  -57.0000 -120.0000 102

  6 omega   29.00  108.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -94.0000  120.0000 79

  7 omega   49.00   87.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -45.0000    0.0000 38

  8 omega   33.00   83.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -30.0000  -30.0000 50

  9 omega   36.00   70.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -45.0000 -150.0000 34

 10 omega   39.00   96.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -45.0000 -120.0000 57

 11 omega   82.00  178.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   30.0000 -120.0000 96

 12 omega   84.00  178.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   30.0000  150.0000 94

 13 omega   36.00   94.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -45.0000  120.0000 58

 14 omega   26.00  108.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -94.0000    0.0000 82
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0805870000
_diffrn_orient_matrix_UB_12      0.0386260000
_diffrn_orient_matrix_UB_13      -0.0469037000
_diffrn_orient_matrix_UB_21      -0.0388835000
_diffrn_orient_matrix_UB_22      -0.0963237000
_diffrn_orient_matrix_UB_23      0.0271129000
_diffrn_orient_matrix_UB_31      -0.0197284000
_diffrn_orient_matrix_UB_32      0.0320919000
_diffrn_orient_matrix_UB_33      0.1381100000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_unetI/netI     0.0136
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            12818
_diffrn_reflns_theta_full        66.50
_diffrn_reflns_theta_max         67.49
_diffrn_reflns_theta_min         4.08
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Cu
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.844
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81463
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) 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    1.311
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         2224
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0318
_refine_ls_R_factor_gt           0.0291
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0407P)^2^+0.9732P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0739
_refine_ls_wR_factor_ref         0.0758
_reflns_number_gt                2056
_reflns_number_total             2224
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo6b00788_si_003.cif
_cod_data_source_block           jwang4cult
_cod_database_code               4036884
_chemical_oxdiff_formula         'C12 H15 O5'
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3A), C4(H4A), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C7(H7A,H7B), C8(H8A,H8B)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3), O4(H4)
;
_olex2_date_sample_data_collection 2015-02-04
_olex2_submission_special_instructions 'No special instructions were received'