Synthesis of 6-Substituted 2-Pyrones Starting from Renewable Resources: Total Synthesis of Sibirinone, (E)-6-(Pent-1-en-1-yl)-2H-pyran-2-one, and (E)-6-(Hept-1-en-1-yl)-2H-pyran-2-one.
Dobler, Daniel; Reiser, Oliver; The Journal of organic chemistry 81 (2016) 10357–10365; doi:10.1021/acs.joc.6b01339

data_4037043
_publ_section_title
;
 Synthesis of 6-Substituted 2-Pyrones Starting from Renewable Resources:
 Total Synthesis of Sibirinone, (E)-6-(Pent-1-en-1-yl)-2H-pyran-2-one, and
 (E)-6-(Hept-1-en-1-yl)-2H-pyran-2-one.
;
_journal_issue                   21
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10357
_journal_page_last               10365
_journal_paper_doi               10.1021/acs.joc.6b01339
_journal_volume                  81
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C13 H12 O4'
_chemical_formula_sum            'C13 H12 O4'
_chemical_formula_weight         232.23
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-11-23
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2015.11.10 svn.r3248 for OlexSys, GUI svn.r5133)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.4205(3)
_cell_length_b                   11.7811(6)
_cell_length_c                   14.1339(6)
_cell_measurement_reflns_used    2825
_cell_measurement_temperature    123.00(10)
_cell_measurement_theta_max      66.3940
_cell_measurement_theta_min      4.8480
_cell_volume                     1069.10(9)
_computing_cell_refinement       'CrysAlisPro 1.171.38.37b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.37b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.37b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      123.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1773
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w   -118.00  -9.00   1.00   25.00    --  -42.01 -77.00   0.00  109
  2  \w    -32.00  66.00   1.00   25.00    --   42.01 -37.00 150.00   98
  3  \w     64.00 158.00   1.00   75.00    --   91.96  30.00-150.00   94
  4  \w     73.00 158.00   1.00   75.00    --   91.96 125.00 -60.00   85
  5  \w     16.00  69.00   1.00   75.00    --   91.96 -30.00 -90.00   53
  6  \w     16.00  69.00   1.00   75.00    --   91.96 -30.00-120.00   53
  7  \w     10.00 108.00   1.00   75.00    --   91.96 -94.00  60.00   98
  8  \w     82.00 150.00   1.00   75.00    --   91.96  30.00-180.00   68
  9  \w    102.00 124.00   1.00   75.00    --   91.96 125.00  30.00   22
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0713466000
_diffrn_orient_matrix_UB_12      0.1283123000
_diffrn_orient_matrix_UB_13      -0.0703571000
_diffrn_orient_matrix_UB_21      -0.0766981000
_diffrn_orient_matrix_UB_22      0.1903554000
_diffrn_orient_matrix_UB_23      0.0176905000
_diffrn_orient_matrix_UB_31      0.0781990000
_diffrn_orient_matrix_UB_32      0.0696260000
_diffrn_orient_matrix_UB_33      0.0814074000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4585
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        66.606
_diffrn_reflns_theta_max         66.606
_diffrn_reflns_theta_min         4.887
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.895
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.937
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.37b (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_description       needle
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.133
_exptl_crystal_size_mid          0.031
_exptl_crystal_size_min          0.023
_refine_diff_density_max         0.352
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 653 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.15(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         1836
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0305
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0449P)^2^+0.1525P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0767
_refine_ls_wR_factor_ref         0.0791
_reflns_Friedel_coverage         0.659
_reflns_Friedel_fraction_full    0.944
_reflns_Friedel_fraction_max     0.944
_reflns_number_gt                1732
_reflns_number_total             1836
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b01339_si_004.cif
_cod_data_source_block           o096
_cod_original_cell_volume        1069.10(8)
_cod_database_code               4037043
_chemical_oxdiff_formula         'C52 H48 O16 '
_chemical_oxdiff_usercomment     'Reiser, Dobler'
_reflns_odcompleteness_completeness 88.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(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:
 C6(H6)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C11(H11), C4(H4), C8(H8), C9(H9), C3(H3A), C2(H2)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_shelx_res_checksum              72779
_shelx_hkl_checksum              88086
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2015-11-18
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.201
_oxdiff_exptl_absorpt_empirical_full_min 0.787