An efficient approach to generate aryl carbenes: gold-catalyzed sequential activation of 1,6-diynes
Cao, Tongxiang; Chen, Kai; Zhu, Shifa; Organic Chemistry Frontiers 4 (2017) 450–; doi:10.1039/C6QO00769D

data_1553620
_publ_section_title
;
 An efficient approach to generate aryl carbenes: gold-catalyzed
 sequential activation of 1,6-diynes
;
_journal_issue                   3
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              450
_journal_paper_doi               10.1039/C6QO00769D
_journal_volume                  4
_journal_year                    2017
_chemical_formula_moiety         'C23 H26 O'
_chemical_formula_sum            'C23 H26 O'
_chemical_formula_weight         318.44
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-05-24
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-11-30 deposited with the CCDC.
2016-12-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.884(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.3103(16)
_cell_length_b                   20.299(3)
_cell_length_c                   6.9248(9)
_cell_measurement_reflns_used    2974
_cell_measurement_temperature    130
_cell_measurement_theta_max      29.42
_cell_measurement_theta_min      2.61
_cell_volume                     1721.3(4)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      130
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_av_unetI/netI     0.0458
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            17008
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.492
_diffrn_reflns_theta_min         1.663
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6831
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0524 before and 0.0466 after correction.
The Ratio of minimum to maximum transmission is 0.9156.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         5226
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0754
_refine_ls_R_factor_gt           0.0487
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0660P)^2^+0.2333P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1184
_refine_ls_wR_factor_ref         0.1330
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3718
_reflns_number_total             5226
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6qo00769d2.cif
_cod_data_source_block           dm16314
_cod_database_code               1553620
_shelx_estimated_absorpt_t_max   0.996
_shelx_estimated_absorpt_t_min   0.989
_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:
 C13(H13), C14(H14), C16(H16), C18(H18)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C15(H15A,H15B), C21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C8(H8)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C)
;
_shelx_res_checksum              78446
_shelx_hkl_checksum              50872
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'