Ligand- and Brønsted acid/base-switchable reaction pathways in gold(i)-catalyzed cycloisomerizations of allenoic acids.
Handa, Sachin; Subramanium, Sri S.; Ruch, Aaron A.; Tanski, Joseph M.; Slaughter, LeGrande M; Organic & biomolecular chemistry 13 (2015) 3936–3949; doi:10.1039/c4ob02640c

data_7154341
_publ_section_title
;
 Ligand- and Br\/onsted acid/base-switchable reaction pathways in
 gold(i)-catalyzed cycloisomerizations of allenoic acids.
;
_journal_issue                   13
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3936
_journal_page_last               3949
_journal_paper_doi               10.1039/c4ob02640c
_journal_volume                  13
_journal_year                    2015
_chemical_formula_moiety         'C23 H24 O2'
_chemical_formula_sum            'C23 H24 O2'
_chemical_formula_weight         332.42
_chemical_melting_point          505.5(5)
_chemical_name_systematic
1-cyclohexyl-4-phenyl-1,2,3,4-tetrahydro-1,4-(epoxymethano)naphthalen-9-one
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2014-04-14 deposited with the CCDC.
2015-02-17 downloaded from the CCDC.
;
_cell_angle_alpha                73.1240(10)
_cell_angle_beta                 89.7970(10)
_cell_angle_gamma                88.8640(10)
_cell_formula_units_Z            4
_cell_length_a                   7.1469(5)
_cell_length_b                   15.3030(10)
_cell_length_c                   16.4534(10)
_cell_measurement_reflns_used    2524
_cell_measurement_temperature    125(2)
_cell_measurement_theta_max      30.40
_cell_measurement_theta_min      2.59
_cell_volume                     1721.7(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      125(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0862
_diffrn_reflns_av_sigmaI/netI    0.1177
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            22822
_diffrn_reflns_theta_full        30.51
_diffrn_reflns_theta_max         30.51
_diffrn_reflns_theta_min         2.16
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.9984
_exptl_absorpt_correction_T_min  0.9810
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'TWINABS Version 2008/4'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             712
_exptl_crystal_recrystallization_method
'slow diff of pentane into ether/dichloromethane soln'
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.382
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     452
_refine_ls_number_reflns         17316
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.1345
_refine_ls_R_factor_gt           0.0626
_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^)+(0.0512P)^2^+2.1711P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1199
_refine_ls_wR_factor_ref         0.1600
_reflns_number_gt                9443
_reflns_number_total             10426
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ob02640c2.cif
_cod_data_source_block           cmpd4a_sh006_ls1465c_0t
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '505-506' was changed to '505.5(5)' -
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

 Adding full bibliography for 7154340--7154342.cif.
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_cod_original_sg_symbol_Hall     -P1
_cod_database_code               7154341