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_4036886
_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 H18 O4'
_chemical_formula_sum            'C12 H18 O4'
_chemical_formula_weight         226.26
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-04-24
_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                 105.7348(19)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.6494(2)
_cell_length_b                   10.45558(17)
_cell_length_c                   9.88362(18)
_cell_measurement_reflns_used    3704
_cell_measurement_temperature    100.2(9)
_cell_measurement_theta_max      75.2080
_cell_measurement_theta_min      5.7820
_cell_volume                     1158.73(4)
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.2(9)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3587
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details
;
  1 omega  114.00  178.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  125.0000 -180.0000 64

  2 omega  -48.00   35.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.9453   37.0000    0.0000 83

  3 omega  -38.00   30.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.9453   37.0000  150.0000 68

  4 omega  -96.00   -2.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.9453  125.0000    0.0000 94

  5 omega -113.00  -12.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.9453  -57.0000 -150.0000 101

  6 omega   36.00   84.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -30.0000 -120.0000 48

  7 omega   49.00  170.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   15.0000 -150.0000 121

  8 omega   85.00  175.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   77.0000 -120.0000 90

  9 omega   51.00  126.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -61.0000 -180.0000 75

 10 omega   58.00  121.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703 -125.0000    0.0000 63

 11 omega   43.00   92.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -45.0000  120.0000 49

 12 omega   36.00  108.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -94.0000  150.0000 72

 13 omega   37.00   98.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -45.0000  -60.0000 61
;
_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      0.0113540000
_diffrn_orient_matrix_UB_12      0.0370748000
_diffrn_orient_matrix_UB_13      0.1539233000
_diffrn_orient_matrix_UB_21      0.0985908000
_diffrn_orient_matrix_UB_22      0.0969569000
_diffrn_orient_matrix_UB_23      -0.0047260000
_diffrn_orient_matrix_UB_31      -0.0949155000
_diffrn_orient_matrix_UB_32      0.1046745000
_diffrn_orient_matrix_UB_33      -0.0501857000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6092
_diffrn_reflns_theta_full        66.50
_diffrn_reflns_theta_max         67.49
_diffrn_reflns_theta_min         5.79
_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    0.796
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93370
_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            colorless
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description
;
;
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         2062
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0320
_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^)+(0.0570P)^2^+0.1814P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0865
_refine_ls_wR_factor_ref         0.0894
_reflns_number_gt                1870
_reflns_number_total             2062
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo6b00788_si_005.cif
_cod_data_source_block           jwang6cult
_cod_original_cell_volume        1158.72(4)
_cod_database_code               4036886
_chemical_oxdiff_formula         'Ph3 O4'
_reflns_odcompleteness_completeness 99.96
_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
2.a Ternary CH refined with riding coordinates:
 C3(H3), C4(H4), 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)
;
_olex2_date_sample_data_collection 2015-03-24
_olex2_submission_special_instructions 'No special instructions were received'