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_4037041
_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 O3'
_chemical_formula_sum            'C17 H16 O3'
_chemical_formula_weight         268.31
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     direct
_audit_creation_date             2016-02-26
_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                 110.522(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.9767(2)
_cell_length_b                   11.8794(2)
_cell_length_c                   11.9166(3)
_cell_measurement_reflns_used    5488
_cell_measurement_temperature    123.01(10)
_cell_measurement_theta_max      73.5780
_cell_measurement_theta_min      4.9580
_cell_volume                     1322.69(5)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      123.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3546
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.0000
_diffrn_measured_fraction_theta_max 0.9884
_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    -98.00  -2.00   1.00    1.50    --  -40.96 125.00 120.00   96
  2  \w   -115.00 -11.00   1.00    1.50    --  -40.96 -57.00 -90.00  104
  3  \w    -41.00  87.00   1.00    1.50    --   40.96 -19.00-150.00  128
  4  \w     32.00  77.00   1.00    6.00    --  106.98 -45.00-180.00   45
  5  \w     23.00 109.00   1.00    6.00    --  106.98 -94.00 120.00   86
  6  \w     23.00 109.00   1.00    6.00    --  106.98 -94.00 -90.00   86
  7  \w     23.00 109.00   1.00    6.00    --  106.98 -94.00-150.00   86
  8  \w     79.00 158.00   1.00    6.00    --  106.98  45.00  30.00   79
  9  \w     73.00 158.00   1.00    6.00    --  106.98  77.00 -60.00   85
 10  \w     77.00 158.00   1.00    6.00    --  106.98  61.00-120.00   81
 11  \w     73.00 158.00   1.00    6.00    --  106.98  77.00 150.00   85
 12  \w     76.00 158.00   1.00    6.00    --  106.98  30.00   0.00   82
 13  \w     32.00  77.00   1.00    6.00    --  106.98 -45.00-120.00   45
 14  \w     32.00 121.00   1.00    6.00    --  106.98-125.00  60.00   89
 15  \w   -115.00 -11.00   1.00    1.50    --  -40.96 -57.00  30.00  104
 16  \w      7.00 120.00   1.00    1.50    --   40.96  77.00-180.00  113
 17  \w      2.00  98.00   1.00    1.50    --   40.96-125.00  90.00   96
 18  \w     29.00  69.00   1.00    6.00    --  106.98 -30.00 -90.00   40
 19  \w     77.00 158.00   1.00    6.00    --  106.98  61.00-150.00   81
 20  \w     73.00 111.00   1.00    6.00    --  106.98  77.00 -90.00   38
 21  \w     76.00 158.00   1.00    6.00    --  106.98  30.00 120.00   82
;
_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      0.0598717000
_diffrn_orient_matrix_UB_12      0.0590397000
_diffrn_orient_matrix_UB_13      -0.0875615000
_diffrn_orient_matrix_UB_21      -0.0609630000
_diffrn_orient_matrix_UB_22      0.1129329000
_diffrn_orient_matrix_UB_23      0.0237649000
_diffrn_orient_matrix_UB_31      0.1410947000
_diffrn_orient_matrix_UB_32      0.0238428000
_diffrn_orient_matrix_UB_33      0.1040184000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12773
_diffrn_reflns_theta_full        67.5000
_diffrn_reflns_theta_max         73.41
_diffrn_reflns_theta_min         5.00
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.741
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87872
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.3473
_exptl_crystal_description       irregular
_exptl_crystal_F_000             569.8709
_exptl_crystal_size_max          0.242
_exptl_crystal_size_mid          0.153
_exptl_crystal_size_min          0.105
_refine_diff_density_max         0.2605
_refine_diff_density_min         -0.2237
_refine_diff_density_rms         0.0466
_refine_ls_d_res_high            0.8044
_refine_ls_d_res_low             8.8529
_refine_ls_goodness_of_fit_ref   1.0660
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    31
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2633
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0660
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0357
_refine_ls_shift/su_max          0.0006
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0486P)^2^+0.3053P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0910
_refine_ls_wR_factor_ref         0.0959
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              7
_reflns_limit_h_min              -12
_reflns_limit_k_max              14
_reflns_limit_k_min              0
_reflns_limit_l_max              14
_reflns_limit_l_min              -7
_reflns_number_gt                2262
_reflns_number_total             2633
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            jo6b01339_si_003.cif
_cod_data_source_block           P025
_cod_original_cell_volume        1322.70(6)
_cod_original_sg_symbol_Hall     '-P 2ybc (x-z,y,z)'
_cod_database_code               4037041
_chemical_oxdiff_formula         'C17 H16 O3'
_chemical_oxdiff_usercomment     'Dobler_Reiser_DD 392'
_reflns_odcompleteness_completeness 99.96
_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:
 C009(H009), C00A(H00A), C00C(H00C), C00D(H00D), C00H(H00H), C00J(H00J)
2.b Secondary CH2 refined with riding coordinates:
 C00K(H00k,H00l)
2.c Aromatic/amide H refined with riding coordinates:
 C007(H007), C008(H008), C00B(H00B), C00E(H00E), C00F(H00F), C00G(H00G),
 C00I(H00I)
2.d Idealised tetrahedral OH refined as rotating group:
 O003(H003)
;
_olex2_date_sample_data_collection 2016-02-24
_olex2_date_sample_submission    2016-02-24
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder oil'
_olex2_submission_original_sample_id P025
_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 1.231
_oxdiff_exptl_absorpt_empirical_full_min 0.759