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_4037042
_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_formula_moiety         'C17 H16 O2'
_chemical_formula_sum            'C17 H16 O2'
_chemical_formula_weight         252.30
_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
_audit_creation_date             2016-02-29
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2016.02.24 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 106.701(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.2968(4)
_cell_length_b                   10.0528(3)
_cell_length_c                   11.7838(4)
_cell_measurement_reflns_used    4317
_cell_measurement_temperature    123.00(10)
_cell_measurement_theta_max      73.3530
_cell_measurement_theta_min      4.0410
_cell_volume                     1281.77(8)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41h (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41h (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41h (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 10.3546
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.983
_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   -117.00 -15.00   1.00    7.50    --  -40.89 -37.00 150.00  102
  2  \w   -115.00 -11.00   1.00    7.50    --  -40.89 -57.00  90.00  104
  3  \w   -117.00 -15.00   1.00    7.50    --  -40.89 -37.00-120.00  102
  4  \w      2.00  98.00   1.00    7.50    --   40.89-125.00-180.00   96
  5  \w     73.00 158.00   1.00   30.00    --  106.98 125.00-180.00   85
  6  \w     77.00 158.00   1.00   30.00    --  106.98  61.00  30.00   81
  7  \w     32.00  77.00   1.00   30.00    --  106.98 -45.00  90.00   45
  8  \w     32.00  79.00   1.00   30.00    --  106.98 -47.00-165.00   47
  9  \w     73.00 158.00   1.00   30.00    --  106.98 125.00-150.00   85
 10  \w     73.00 158.00   1.00   30.00    --  106.98  77.00  60.00   85
 11  \w     73.00 158.00   1.00   30.00    --  106.98  77.00  90.00   85
 12  \w     32.00  77.00   1.00   30.00    --  106.98 -45.00-120.00   45
 13  \w     77.00 158.00   1.00   30.00    --  106.98  61.00  60.00   81
 14  \w     73.00 158.00   1.00   30.00    --  106.98 125.00 120.00   85
 15  \w     29.00  69.00   1.00   30.00    --  106.98 -30.00 -30.00   40
 16  \w     79.00 158.00   1.00   30.00    --  106.98  45.00-150.00   79
 17  \w     79.00 158.00   1.00   30.00    --  106.98  45.00 150.00   79
 18  \w     32.00 121.00   1.00   30.00    --  106.98-125.00   0.00   89
 19  \w   -115.00 -11.00   1.00    7.50    --  -40.89 -57.00   0.00  104
 20  \w      2.00  27.00   1.00    7.50    --   40.89-125.00 -90.00   25
;
_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      -0.1227741000
_diffrn_orient_matrix_UB_12      -0.0013767000
_diffrn_orient_matrix_UB_13      -0.1001191000
_diffrn_orient_matrix_UB_21      0.0595788000
_diffrn_orient_matrix_UB_22      -0.0887572000
_diffrn_orient_matrix_UB_23      -0.0750184000
_diffrn_orient_matrix_UB_31      -0.0409220000
_diffrn_orient_matrix_UB_32      -0.1248647000
_diffrn_orient_matrix_UB_33      0.0544879000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11218
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.500
_diffrn_reflns_theta_max         73.509
_diffrn_reflns_theta_min         4.086
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.670
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.987
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41h (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
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    1.307
_exptl_crystal_description       plate
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.112
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.037
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2541
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0358
_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^)+(0.0394P)^2^+0.4759P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0852
_refine_ls_wR_factor_ref         0.0909
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2172
_reflns_number_total             2541
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b01339_si_002.cif
_cod_data_source_block           p026
_cod_database_code               4037042
_chemical_oxdiff_formula         'C17 H16 O2'
_chemical_oxdiff_usercomment     Dobler_Reiser_DD383
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C11(H11), C15(H15), C7(H7), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C12(H12), C13(H13), C1(H1A), C6(H6), C5(H5), C3(H3), C4(H4)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              39694
_shelx_hkl_checksum              45991
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-02-25
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems CryoStream 700'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder oil'
_olex2_submission_original_sample_id 'DD 383'
_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 1.207
_oxdiff_exptl_absorpt_empirical_full_min 0.719