Selective Vinylogous Reactivity of Carbene Intermediate in Gold-Catalyzed Alkyne Carbocyclization: Synthesis of Indenols
Zhang, Cheng; Li, Hongli; Pei, Chao; Qiu, Lihua; Hu, Wenhao; Bao, Xiaoguang; Xu, Xinfang; ACS Catalysis 9 (2019) 2440–; doi:10.1021/acscatal.8b04144

data_4514866
_publ_section_title
;
 Selective Vinylogous Reactivity of Carbene Intermediate in Gold-Catalyzed
 Alkyne Carbocyclization: Synthesis of Indenols
;
_journal_issue                   3
_journal_name_full               'ACS Catalysis'
_journal_page_first              2440
_journal_paper_doi               10.1021/acscatal.8b04144
_journal_volume                  9
_journal_year                    2019
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C27 H32 O3'
_chemical_formula_sum            'C27 H32 O3'
_chemical_formula_weight         404.53
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-07-04
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2017.06.29 svn.r3433 for OlexSys, GUI svn.r5356)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 94.588(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.720(2)
_cell_length_b                   7.5084(18)
_cell_length_c                   16.171(4)
_cell_measurement_reflns_used    7844
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      26.24
_cell_measurement_theta_min      2.36
_cell_volume                     1176.4(5)
_computing_cell_refinement       'Bruker D8 Quest'
_computing_data_collection       'Bruker D8 Quest'
_computing_data_reduction        'Bruker D8 Quest'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120.02
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0749
_diffrn_reflns_av_unetI/netI     0.0892
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            19723
_diffrn_reflns_theta_full        27.52
_diffrn_reflns_theta_max         27.52
_diffrn_reflns_theta_min         2.99
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_correction_T_min  0.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 Sheldrick, G.M. SADABS (Program for Scaling and Correction of Area Detector
 Data), version 2008/1; University of G\"ottingen: G\"ottingen, Germany, 2008.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.142
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.2(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         5355
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.1100
_refine_ls_R_factor_gt           0.0554
_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^)+(0.0554P)^2^+0.1088P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1149
_refine_ls_wR_factor_ref         0.1346
_reflns_number_gt                3579
_reflns_number_total             5355
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cs8b04144_si_004.cif
_cod_data_source_block           zc
_cod_database_code               4514866
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C18(H18), C20(H20), C23(H23), C25(H25)
2.b Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C21(H21A,H21B), C22(H22A,H22B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C24(H24A,H24B,H24C), C26(H26A,H26B,H26C), C27(H27A,H27B,
 H27C)
;
_olex2_submission_special_instructions 'No special instructions were received'