Gold(i)- and platinum(iv)-catalyzed intramolecular annulations of allenes towards furans
Liu, Cheng-Hang; Yu, Zhi-Xiang; Org. Chem. Front. 1 (2014) 1205–; doi:10.1039/C4QO00223G

data_1553034
_publ_section_title
;
 Gold(i)- and platinum(iv)-catalyzed intramolecular annulations of allenes
 towards furans
;
_journal_issue                   10
_journal_name_full               'Org. Chem. Front.'
_journal_page_first              1205
_journal_paper_doi               10.1039/C4QO00223G
_journal_volume                  1
_journal_year                    2014
_chemical_formula_moiety         'C21 H17 Br2 N O3 S'
_chemical_formula_sum            'C21 H17 Br2 N O3 S'
_chemical_formula_weight         523.24
_chemical_properties_physical    Oxygen-sensitive
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2014-04-28
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_cell_angle_alpha                90
_cell_angle_beta                 106.900(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.4812(7)
_cell_length_b                   8.1107(6)
_cell_length_c                   13.3671(9)
_cell_measurement_reflns_used    1847
_cell_measurement_temperature    180.00(10)
_cell_measurement_theta_max      27.6410
_cell_measurement_theta_min      3.4420
_cell_volume                     983.53(13)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      180.00(10)
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 0.9861
_diffrn_measured_fraction_theta_max 0.6080
_diffrn_measurement_details
;
  1 omega  -23.00   56.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       10.7017   77.0000    0.0000 79

  2 omega    2.00   83.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       10.7017   38.0000  -90.0000 81
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0685271000
_diffrn_orient_matrix_UB_12      0.0195340000
_diffrn_orient_matrix_UB_13      0.0085188000
_diffrn_orient_matrix_UB_21      -0.0368990000
_diffrn_orient_matrix_UB_22      -0.0179044000
_diffrn_orient_matrix_UB_23      -0.0531300000
_diffrn_orient_matrix_UB_31      -0.0082272000
_diffrn_orient_matrix_UB_32      -0.0832808000
_diffrn_orient_matrix_UB_33      0.0134284000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0673
_diffrn_reflns_av_unetI/netI     0.0996
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3819
_diffrn_reflns_point_group_measured_fraction_full 0.750
_diffrn_reflns_point_group_measured_fraction_max 0.737
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.020
_diffrn_reflns_theta_min         2.974
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    4.250
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56240
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'colorless '
_exptl_crystal_density_diffrn    1.767
_exptl_crystal_F_000             520
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DCM/n-Octane'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.865
_refine_diff_density_min         -0.759
_refine_diff_density_rms         0.135
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.04(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         2860
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0816
_refine_ls_R_factor_gt           0.0628
_refine_ls_shift/su_max          0.021
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1020P)^2^+0.1273P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1638
_refine_ls_wR_factor_ref         0.1843
_reflns_Friedel_coverage         0.389
_reflns_Friedel_fraction_full    0.473
_reflns_Friedel_fraction_max     0.446
_reflns_number_gt                2264
_reflns_number_total             2860
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4qo00223g2.cif
_cod_data_source_block           3
_cod_original_cell_volume        983.53(12)
_cod_database_code               1553034
_chemical_oxdiff_formula         'C21 O3 Br2 N1 S1'
_reflns_odcompleteness_completeness 98.61
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C7(H7A,H7B), C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C8(H8), C11(H11), C12(H12), C14(H14), C15(H15), C17(H17),
 C18(H18), C20(H20), C21(H21)
;
_shelx_estimated_absorpt_t_max   0.676
_shelx_estimated_absorpt_t_min   0.484
_shelxl_version_number           2013-3