Synthesis of 5-hydroxycyclopent-2-enones from allenyl vinyl ketones via an interrupted Nazarov cyclization.
Marx, Vanessa M.; Burnell, D. Jean; Organic letters 11 (2009) 1229–1231; doi:10.1021/ol900029d

data_1503807
_publ_section_title
;
 Synthesis of 5-hydroxycyclopent-2-enones from allenyl vinyl ketones via
 an interrupted Nazarov cyclization.
;
_journal_issue                   6
_journal_name_full               'Organic letters'
_journal_page_first              1229
_journal_page_last               1231
_journal_paper_doi               10.1021/ol900029d
_journal_volume                  11
_journal_year                    2009
_chemical_formula_moiety         'C13 H14 O2 '
_chemical_formula_sum            'C13 H14 O2'
_chemical_formula_weight         202.25
_chemical_melting_point          351.6(5)
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_cell_angle_alpha                90.0000
_cell_angle_beta                 106.022(3)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            8
_cell_length_a                   18.7028(14)
_cell_length_b                   5.9021(2)
_cell_length_c                   20.8680(12)
_cell_measurement_reflns_used    9497
_cell_measurement_temperature    120.1
_cell_measurement_theta_max      72.4
_cell_measurement_theta_min      2.3
_cell_volume                     2214.1(2)
_computing_cell_refinement       PROCESS
_computing_data_collection       PROCESS
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.8'
_computing_structure_refinement  CRYSTALS
_computing_structure_solution    SHELXS97
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.842
_diffrn_measurement_device_type  'Rigaku RAXIS-UNKNOWN'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.035
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -49
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       51
_diffrn_reflns_limit_l_min       -53
_diffrn_reflns_number            41835
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         72.34
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.819
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
    Higashi, T. (1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             864.00
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.51
_refine_diff_density_min         -0.25
_refine_ls_extinction_coef       15(13)
_refine_ls_extinction_method
'Larson (1970) Crystallographic Computing eq. 22'
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     178
_refine_ls_number_reflns         1841
_refine_ls_R_factor_gt           0.0634
_refine_ls_shift/su_max          0.0039
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
    Chebychev polynomial with 3 parameters (Carruthers & Watkin, 1979)
    9.8132    5.0194    6.4664
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0795
_reflns_number_gt                1841
_reflns_number_total             2156
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ol900029d_si_002.cif
_cod_data_source_block           '__JB12'
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '78-79 degree C' was changed to
'351.6(5)' - it was converted from degrees Celsius(C) to Kelvins(K),
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        2214.0(2)
_cod_original_formula_sum        'C13 H14 O2 '
_cod_database_code               1503807