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_7154340
_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          368.5(15)
_chemical_name_systematic
5-(cyclohexylidenemethyl)-3,3-diphenyldihydrofuran-2(3H)-one
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2014-04-14 deposited with the CCDC.
2015-02-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.1728(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.28820(10)
_cell_length_b                   10.08340(10)
_cell_length_c                   17.6278(2)
_cell_measurement_reflns_used    9853
_cell_measurement_temperature    125(2)
_cell_measurement_theta_max      68.75
_cell_measurement_theta_min      5.07
_cell_volume                     1799.96(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL (XP)'
_computing_publication_material  'Bruker SHELXTL (XCIF)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      125(2)
_diffrn_detector_area_resol_mean 0.75
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_av_unetI/netI     0.0170
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            26227
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        66.595
_diffrn_reflns_theta_max         66.595
_diffrn_reflns_theta_min         4.366
_diffrn_standards_decay_%        N/A
_diffrn_standards_interval_count N/A
_diffrn_standards_interval_time  N/A
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.598
_exptl_absorpt_correction_T_max  0.865
_exptl_absorpt_correction_T_min  0.796
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_density_meas      ?
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_recrystallization_method
'slow diff of pentane into ether/dichloromethane soln'
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.250
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       0.0029(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3169
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0345
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0348P)^2^+0.7764P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0841
_refine_ls_wR_factor_ref         0.0844
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3122
_reflns_number_total             3169
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4ob02640c2.cif
_cod_data_source_block           cmpd2a_sh009
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '367-370' was changed to '368.5(15)'
- the average value was taken and precision was estimated.

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

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

 Adding full bibliography for 7154340--7154342.cif.
;
_cod_database_code               7154340
_shelx_estimated_absorpt_t_min   0.796
_shelx_estimated_absorpt_t_max   0.865
_shelxl_version_number           2013-4
_shelx_res_checksum              3969