A selective C-H insertion/olefination protocol for the synthesis of α-methylene-γ-butyrolactone natural products.
Lloyd, Matthew G.; D'Acunto, Mariantonietta; Taylor, Richard J. K.; Unsworth, William P.; Organic & biomolecular chemistry 14 (2016) 1641–1645; doi:10.1039/c5ob02579f

data_7154852
_publ_section_title
;
 A selective C-H insertion/olefination protocol for the synthesis of
 \a-methylene-\g-butyrolactone natural products.
;
_journal_issue                   5
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1641
_journal_page_last               1645
_journal_paper_doi               10.1039/c5ob02579f
_journal_volume                  14
_journal_year                    2016
_chemical_formula_moiety         'C15 H20 O2'
_chemical_formula_sum            'C15 H20 O2'
_chemical_formula_weight         232.31
_chemical_melting_point          340.0(10)
_chemical_name_systematic
(3aRS,5aRS,9aRS,9bRS)-5a-methyl-3,9-dimethylenedecahydronaphtho[1,2-b]furan-2(9bH)-one
_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_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-03-02
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-08-28 deposited with the CCDC.
2015-12-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.654(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   6.95182(16)
_cell_length_b                   12.2280(3)
_cell_length_c                   30.5046(6)
_cell_measurement_reflns_used    953
_cell_measurement_temperature    110.05(10)
_cell_measurement_theta_max      44.2870
_cell_measurement_theta_min      5.6660
_cell_volume                     2580.48(10)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      110.05(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1450
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -10.00   17.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000   30.0000 27

  2 omega  -15.00   20.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000  120.0000 35

  3 omega   23.00   61.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000  120.0000 38

  4 omega   34.00   68.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000   30.0000 34

  5 omega   33.00  113.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000  -60.0000 80

  6 omega    2.00   52.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -99.0000 -120.0000 50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.2164933000
_diffrn_orient_matrix_UB_12      0.0277695000
_diffrn_orient_matrix_UB_13      0.0010276000
_diffrn_orient_matrix_UB_21      -0.0270093000
_diffrn_orient_matrix_UB_22      0.0243795000
_diffrn_orient_matrix_UB_23      -0.0497705000
_diffrn_orient_matrix_UB_31      -0.0446484000
_diffrn_orient_matrix_UB_32      0.1204183000
_diffrn_orient_matrix_UB_33      0.0098411000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0192
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            8613
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.072
_diffrn_reflns_theta_max         67.072
_diffrn_reflns_theta_min         3.897
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.611
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75311
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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    1.196
_exptl_crystal_description       plate
_exptl_crystal_F_000             1008
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: chloroform/diethyl ether'
_exptl_crystal_size_max          0.1215
_exptl_crystal_size_mid          0.081
_exptl_crystal_size_min          0.0366
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         4600
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0487
_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^)+(0.0797P)^2^+0.4903P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1285
_refine_ls_wR_factor_ref         0.1362
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3624
_reflns_number_total             4600
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ob02579f2.cif
_cod_data_source_block           rjkt1506
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '339-341' was changed to '340.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 7154852--7154854.cif.
;
_cod_original_cell_volume        2580.47(10)
_cod_database_code               7154852
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         'C16 H20 O2'
_chemical_oxdiff_usercomment     'Matthew MGL/06/58-P1'
_reflns_odcompleteness_completeness 27.66
_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 C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C18(H18), C19(H19), C20(H20)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C11(H11A,H11B), C12(H12A,H12B),
 C22(H22A,H22B), C23(H23A,H23B), C24(H24A,H24B), C26(H26A,H26B), C27(H27A,H27B)
2.c X=CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B), C28(H28A,H28B), C29(H29A,H29B)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C30(H30A,H30B,H30C)
;
_olex2_date_sample_data_collection 2015-02-10
_olex2_submission_special_instructions 'No special instructions were received'