Gold-catalyzed cascade cyclization-oxidative alkynylation of allenoates.
Hopkinson, Matthew N.; Ross, Jonathan E.; Giuffredi, Guy T.; Gee, Antony D.; Gouverneur, Véronique; Organic letters 12 (2010) 4904–4907; doi:10.1021/ol102061k

data_1503260
_publ_section_title
;
 Gold-catalyzed cascade cyclization-oxidative alkynylation of allenoates.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              4904
_journal_page_last               4907
_journal_paper_doi               10.1021/ol102061k
_journal_volume                  12
_journal_year                    2010
_chemical_formula_moiety         'C12 H10 O2'
_chemical_formula_sum            'C12 H10 O2'
_chemical_formula_weight         186.21
_chemical_melting_point          ?
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             10-03-23
_audit_creation_method           CRYSTALS_ver_14.06
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.8904(2)
_cell_length_b                   13.3099(2)
_cell_length_c                   13.8982(2)
_cell_measurement_reflns_used    2362
_cell_measurement_temperature    150
_cell_measurement_theta_max      27
_cell_measurement_theta_min      5
_cell_volume                     1829.56(5)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2001).'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.018
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            32432
_diffrn_reflns_theta_full        27.447
_diffrn_reflns_theta_max         27.447
_diffrn_reflns_theta_min         5.095
_diffrn_standards_decay_%        'not measured'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.34
_refine_diff_density_min         -0.30
_refine_ls_extinction_coef       200(100)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   0.9260
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         2071
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0461
_refine_ls_shift/su_max          0.0004138
_refine_ls_shift/su_mean         0.0000583
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.10P)^2^ + 0.39P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1353
_refine_ls_wR_factor_gt          0.1249
_refine_ls_wR_factor_ref         0.1353
_reflns_limit_h_max              12
_reflns_limit_h_min              0
_reflns_limit_k_max              17
_reflns_limit_k_min              0
_reflns_limit_l_max              18
_reflns_limit_l_min              0
_reflns_number_gt                1608
_reflns_number_total             2071
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.71
_oxford_diffrn_Wilson_scale      4.25
_oxford_refine_ls_r_factor_ref   0.0598
_oxford_refine_ls_scale          0.4727(18)
_oxford_reflns_number_all        2071
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_oxford_structure_analysis_title 010GG328MH01
_cod_data_source_file            ol102061k_si_003.cif
_cod_data_source_block           5
_cod_depositor_comments
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The following automatic conversions were performed:

'_chemical_melting_point' value 'not measured' was changed to '?' -
the value is undefined or not given.

'_symmetry_cell_setting' value
'Orthorhombic' changed to 'orthorhombic' 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 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P b c a '
_cod_database_code               1503260