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_1508844
_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         'C15 H18 O4'
_chemical_formula_sum            'C15 H18 O4'
_chemical_formula_weight         262.29
_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             2012-08-10
_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                 99.952(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.5908(4)
_cell_length_b                   12.0381(3)
_cell_length_c                   7.2191(2)
_cell_measurement_reflns_used    3714
_cell_measurement_temperature    173.15
_cell_measurement_theta_max      71.2712
_cell_measurement_theta_min      4.6635
_cell_volume                     1334.52(6)
_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 0.972
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_details
;
  1 omega   39.00   90.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000 -111.0000    0.0000 51

  2 omega   40.00   72.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000  -25.0000 -150.0000 32

  3 omega  -24.00   21.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000 -120.0000 45

  4 omega -113.00  -49.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -55.0000  128.0000  144.0000 64

  5 omega   75.00  123.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       55.0000  125.0000 -150.0000 48

  6 omega   34.00   85.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       55.0000   38.0000 -150.0000 51

  7 omega  -65.00    8.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -64.0000   38.0000  -30.0000 73

  8 omega   39.00   69.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000  -25.0000   30.0000 30

  9 omega   42.00   83.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000  -50.0000   60.0000 41

 10 omega   57.00   89.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000 -111.0000   60.0000 32

 11 omega   37.00   72.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000  -25.0000 -180.0000 35

 12 omega   47.00   83.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000  -50.0000  150.0000 36

 13 omega   40.00   69.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000  -38.0000  120.0000 29

 14 omega   41.00   69.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000  -38.0000   90.0000 28

 15 omega   49.00   85.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000 -111.0000   90.0000 36

 16 omega   54.00  141.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000  -92.0000  150.0000 87

 17 omega  -30.00   70.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   77.0000  -30.0000 100

 18 omega -124.00  -34.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -55.0000  -57.0000 -120.0000 90

 19 omega -125.00 -100.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -55.0000  -77.0000   90.0000 25
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0490580000
_diffrn_orient_matrix_UB_12      0.1169152000
_diffrn_orient_matrix_UB_13      0.0294481000
_diffrn_orient_matrix_UB_21      -0.0659197000
_diffrn_orient_matrix_UB_22      0.0336222000
_diffrn_orient_matrix_UB_23      -0.0957214000
_diffrn_orient_matrix_UB_31      -0.2004839000
_diffrn_orient_matrix_UB_32      -0.0396953000
_diffrn_orient_matrix_UB_33      0.0056302000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0192
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            4956
_diffrn_reflns_theta_full        66.50
_diffrn_reflns_theta_max         66.98
_diffrn_reflns_theta_min         4.67
_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    0.772
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85292
_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    1.305
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.136
_refine_diff_density_rms         0.029
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2312
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0329
_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^)+(0.0479P)^2^+0.2317P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0863
_refine_ls_wR_factor_ref         0.0881
_reflns_number_gt                2164
_reflns_number_total             2312
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol303071t_si_002.cif
_cod_data_source_block           song2
_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               1508844
_reflns_odcompleteness_completeness 97.61
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13