Asymmetric Total Syntheses of (-)-Penicipyrone and (-)-Tenuipyrone via Biomimetic Cascade Intermolecular Michael Addition/Cycloketalization.
Song, Liyan; Yao, Hongliang; Zhu, Liangyu; Tong, Rongbiao; Organic letters 15 (2013) 6–9; doi:10.1021/ol303071t

data_1508845
_publ_section_title
;
 Asymmetric Total Syntheses of (-)-Penicipyrone and (-)-Tenuipyrone via
 Biomimetic Cascade Intermolecular Michael Addition/Cycloketalization.
;
_journal_issue                   1
_journal_name_full               'Organic letters'
_journal_page_first              6
_journal_page_last               9
_journal_paper_doi               10.1021/ol303071t
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C13 H16 O4'
_chemical_formula_sum            'C13 H16 O4'
_chemical_formula_weight         236.26
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2012-07-30
_audit_creation_method
;
  Olex2 1.2-beta
  (compiled May  9 2012 12:37:22, GUI svn.r4230)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 110.216(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.6914(2)
_cell_length_b                   9.8462(2)
_cell_length_c                   11.5299(2)
_cell_measurement_reflns_used    4298
_cell_measurement_temperature    173.00(14)
_cell_measurement_theta_max      71.2884
_cell_measurement_theta_min      4.0825
_cell_volume                     1138.98(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_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      173.00(14)
_diffrn_detector_area_resol_mean 15.9578
_diffrn_measured_fraction_theta_full 0.9793
_diffrn_measured_fraction_theta_max 0.9595
_diffrn_measurement_details
;
  1 omega  -92.00  -21.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -64.0000   77.0000   60.0000 71

  2 omega   16.00   42.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000  -90.0000 26

  3 omega  -85.00  -18.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -55.0000  125.0000  120.0000 67

  4 omega   76.00   97.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       55.0000  125.0000   60.0000 21

  5 omega  -17.00   52.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       55.0000  -38.0000   60.0000 69

  6 omega   14.00  127.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       55.0000   19.0000   60.0000 113

  7 omega -110.00  -58.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -64.0000  178.0000  150.0000 52

  8 omega   46.00   72.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000  -92.0000  -60.0000 26

  9 omega   38.00   71.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000  -25.0000  120.0000 33

 10 omega  140.00  175.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000   50.0000  150.0000 35

 11 omega   40.00   83.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000  -50.0000 -150.0000 43

 12 omega   41.00   68.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000  -25.0000  -30.0000 27

 13 omega   83.00  147.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000  -92.0000  -60.0000 64

 14 omega   37.00   68.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000  -25.0000 -120.0000 31

 15 omega   90.00  136.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000   50.0000  150.0000 46

 16 omega   42.00   76.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000  -50.0000  -30.0000 34

 17 omega   37.00   72.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000  -25.0000  -90.0000 35

 18 omega   46.00   76.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000  -92.0000 -150.0000 30

 19 omega   40.00   82.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000  -50.0000   60.0000 42

 20 omega   37.00   72.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000  -25.0000    0.0000 35

 21 omega   95.00  177.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000   25.0000  -90.0000 82

 22 omega   38.00   72.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000  -25.0000  150.0000 34

 23 omega   62.00  148.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000  -92.0000   60.0000 86

 24 omega  -25.00    3.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000  -90.0000 28
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0421247000
_diffrn_orient_matrix_UB_12      0.1351703000
_diffrn_orient_matrix_UB_13      -0.0697521000
_diffrn_orient_matrix_UB_21      0.0596381000
_diffrn_orient_matrix_UB_22      0.0784357000
_diffrn_orient_matrix_UB_23      0.1224932000
_diffrn_orient_matrix_UB_31      0.1351060000
_diffrn_orient_matrix_UB_32      0.0075805000
_diffrn_orient_matrix_UB_33      -0.0199160000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5772
_diffrn_reflns_theta_full        66.50
_diffrn_reflns_theta_max         67.48
_diffrn_reflns_theta_min         6.30
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           35
_diffrn_source_power             1.75
_diffrn_source_target            Cu
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.841
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83425
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.034
_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     156
_refine_ls_number_reflns         2010
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_gt           0.0337
_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^)+(0.0496P)^2^+0.2217P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0899
_refine_ls_wR_factor_ref         0.0925
_reflns_number_gt                1870
_reflns_number_total             2010
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol303071t_si_003.cif
_cod_data_source_block           song1cult
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1508845
_reflns_odcompleteness_completeness 97.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13