Selective Syntheses of Δα,βand Δβ,γButenolides from Allylic Cyclopropenecarboxylates via Tandem Ring Expansion/[3,3]-Sigmatropic Rearrangements
Xie, Xiaocong; Li, Yi; Fox, Joseph M.; Organic Letters 15 (2013) 1500–; doi:10.1021/ol400264a

data_1511864
_publ_section_title
;
 Selective Syntheses of \D\a,\band \D\b,\gButenolides from Allylic
 Cyclopropenecarboxylates via Tandem Ring Expansion/[3,3]-Sigmatropic
 Rearrangements
;
_journal_issue                   7
_journal_name_full               'Organic Letters'
_journal_page_first              1500
_journal_paper_doi               10.1021/ol400264a
_journal_volume                  15
_journal_year                    2013
_chemical_formula_sum            'C16 H16 O2'
_chemical_formula_weight         240.29
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.484(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.487(5)
_cell_length_b                   6.052(3)
_cell_length_c                   36.080(8)
_cell_measurement_reflns_used    991
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      27.95
_cell_measurement_theta_min      2.27
_cell_volume                     2492.2(17)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2001)'
_computing_publication_material  'SHELXTL (Sheldrick, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 836.6
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker AXS APEX diffractometer'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0647
_diffrn_reflns_av_sigmaI/netI    0.0465
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            11114
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.27
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.9959
_exptl_absorpt_correction_T_min  0.9761
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.472
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2197
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0928
_refine_ls_R_factor_gt           0.0863
_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^)+(0.1769P)^2^+7.9447P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2671
_refine_ls_wR_factor_ref         0.2747
_reflns_number_gt                1953
_reflns_number_total             2197
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol400264a_si_001.cif
_cod_data_source_block           joef103
_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_cell_volume        2492.1(16)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               1511864