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_1503259
_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_absolute_configuration unk
_chemical_formula_moiety         'C20 H16 O2'
_chemical_formula_sum            'C20 H16 O2'
_chemical_formula_weight         288.35
_chemical_melting_point          ?
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P -2n 2a'
_symmetry_space_group_name_H-M   'P 21 c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             10-03-19
_audit_creation_method           CRYSTALS_ver_14.06
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.3338(2)
_cell_length_b                   12.6452(5)
_cell_length_c                   19.4647(9)
_cell_measurement_reflns_used    1598
_cell_measurement_temperature    150
_cell_measurement_theta_max      25
_cell_measurement_theta_min      5
_cell_volume                     1558.97(11)
_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 0.988
_diffrn_measured_fraction_theta_max 0.988
_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  0.023
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            6847
_diffrn_reflns_theta_full        25.343
_diffrn_reflns_theta_max         25.343
_diffrn_reflns_theta_min         5.272
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.98
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.16
_refine_diff_density_min         -0.15
_refine_ls_extinction_coef       420(90)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   0.9601
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         1549
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0318
_refine_ls_shift/su_max          0.0002851
_refine_ls_shift/su_mean         0.0000331
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.05P)^2^ + 0.19P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0801
_refine_ls_wR_factor_gt          0.0767
_refine_ls_wR_factor_ref         0.0801
_reflns_limit_h_max              7
_reflns_limit_h_min              0
_reflns_limit_k_max              15
_reflns_limit_k_min              0
_reflns_limit_l_max              23
_reflns_limit_l_min              0
_reflns_number_gt                1371
_reflns_number_total             1549
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.89
_oxford_diffrn_Wilson_scale      1.35
_oxford_refine_ls_r_factor_ref   0.0383
_oxford_refine_ls_scale          0.875(4)
_oxford_reflns_number_all        1549
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_oxford_structure_analysis_title 009GG052JR03
_cod_data_source_file            ol102061k_si_002.cif
_cod_data_source_block           3fa
_cod_depositor_comments
;
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 21 c n '
_cod_database_code               1503259