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_7154342
_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         'C24 H26 O3'
_chemical_formula_sum            'C24 H26 O3'
_chemical_formula_weight         362.45
_chemical_name_systematic
;        
2-methoxy-4-phenyl-4,5,5a,6,6a,7,8,9,10,10a-decahydroacephenanthrylene-
4-carboxylic acid
;
_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                78.548(2)
_cell_angle_beta                 77.234(2)
_cell_angle_gamma                64.389(3)
_cell_formula_units_Z            2
_cell_length_a                   9.7954(4)
_cell_length_b                   9.8427(4)
_cell_length_c                   11.0909(5)
_cell_measurement_reflns_used    8356
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.27
_cell_measurement_theta_min      2.31
_cell_volume                     933.94(7)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'SMART (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD Bruker APEX'
_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  0.0154
_diffrn_reflns_av_sigmaI/netI    0.0142
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            17614
_diffrn_reflns_theta_full        25.25
_diffrn_reflns_theta_max         28.30
_diffrn_reflns_theta_min         1.90
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.9983
_exptl_absorpt_correction_T_min  0.9579
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldirck, 2001)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             388
_exptl_crystal_recrystallization_method
'slow diff of pentane into ether/dichloromethane soln'
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.422
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     303
_refine_ls_number_reflns         4626
_refine_ls_number_restraints     322
_refine_ls_restrained_S_all      0.997
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0431
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0800P)^2^+0.2800P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1193
_refine_ls_wR_factor_ref         0.1243
_reflns_number_gt                4139
_reflns_number_total             4626
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            c4ob02640c2.cif
_cod_data_source_block           cmpd9_sh012_12115
_cod_depositor_comments
;Adding full bibliography for 7154340--7154342.cif.

The following automatic conversions were performed:

data name '_iucr_refine_instruction_details' was replaced with
'_iucr_refine_instructions_details' as specified in the replacement
file 'data/replacement-values/replacement_tags.lst'.

Automatic conversion script
Id: cif_correct_tags 9268 2022-04-12 08:56:07Z antanas 
;
_cod_database_code               7154342