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_4036883
_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_absolute_configuration ad
_chemical_formula_moiety         'C12 H20 O4'
_chemical_formula_sum            'C12 H20 O4'
_chemical_formula_weight         228.28
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-01-19
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.12 svn.r3133 for OlexSys, GUI svn.r4987)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.05049(8)
_cell_length_b                   11.43870(12)
_cell_length_c                   12.60616(16)
_cell_measurement_reflns_used    5125
_cell_measurement_temperature    99.9(5)
_cell_measurement_theta_max      75.9880
_cell_measurement_theta_min      5.2070
_cell_volume                     1160.87(2)
_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      99.9(5)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3587
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details
;
  1 omega   94.00  178.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      110.7633  125.0000  -90.0000 84

  2 omega  -49.00   33.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9397   37.0000  -90.0000 82

  3 omega -122.00   -1.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9397  -19.0000   90.0000 121

  4 omega   82.00  178.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      110.7633   30.0000  120.0000 96

  5 omega   34.00   90.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      110.7633  -30.0000 -120.0000 56

  6 omega   82.00  178.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      110.7633   30.0000    0.0000 96

  7 omega   38.00   98.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      110.7633  -45.0000 -180.0000 60

  8 omega   34.00   90.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      110.7633  -30.0000  120.0000 56

  9 omega  -70.00  -11.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9397   57.0000   60.0000 59

 10 omega -118.00   -9.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9397  -77.0000  -60.0000 109

 11 omega  -77.00  -30.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.0022  -57.0000   90.0000 47

 12 omega  -58.00  -32.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.0022  -77.0000   30.0000 26

 13 omega  -91.00  -66.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.0022  -77.0000  150.0000 25

 14 omega   23.00   80.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       42.0022 -125.0000  120.0000 57

 15 omega   83.00  108.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      110.7633   61.0000   60.0000 25

 16 omega  130.00  160.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      110.7633   61.0000   60.0000 30

 17 omega  100.00  130.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      110.7633   30.0000 -120.0000 30
;
_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      0.1510817000
_diffrn_orient_matrix_UB_12      -0.0690694000
_diffrn_orient_matrix_UB_13      -0.0411309000
_diffrn_orient_matrix_UB_21      0.1170352000
_diffrn_orient_matrix_UB_22      0.0827521000
_diffrn_orient_matrix_UB_23      0.0607552000
_diffrn_orient_matrix_UB_31      -0.0092526000
_diffrn_orient_matrix_UB_32      -0.0807522000
_diffrn_orient_matrix_UB_33      0.0977524000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0168
_diffrn_reflns_av_unetI/netI     0.0164
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6678
_diffrn_reflns_theta_full        66.50
_diffrn_reflns_theta_max         67.42
_diffrn_reflns_theta_min         5.22
_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    0.795
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.36666
_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_density_diffrn    1.306
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         2022
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0252
_refine_ls_R_factor_gt           0.0240
_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^)+(0.0371P)^2^+0.2000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0610
_refine_ls_wR_factor_ref         0.0622
_reflns_number_gt                1958
_reflns_number_total             2022
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo6b00788_si_002.cif
_cod_data_source_block           jwang1cult
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Orthorhombic' was changed
to 'orthorhombic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               4036883
_reflns_odcompleteness_completeness 99.84
_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:
 C1(H1), C3(H3A), C4(H4), C5(H5), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 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), O6(H6)
;
_olex2_date_sample_data_collection 2015-01-12
_olex2_submission_special_instructions 'No special instructions were received'