Gold(i)-catalyzed [2 + 2 + 2] cycloaddition of allenamides, alkenes and aldehydes: a straightforward approach to tetrahydropyrans
Faustino, Hélio; Varela, Iván; Mascareñas, José L.; López, Fernando; Chem. Sci. 6 (2015) 2903–; doi:10.1039/C5SC00295H

data_1518845
_publ_section_title
;
 Gold(i)-catalyzed [2 + 2 + 2] cycloaddition of allenamides, alkenes and
 aldehydes: a straightforward approach to tetrahydropyrans
;
_journal_issue                   5
_journal_name_full               'Chem. Sci.'
_journal_page_first              2903
_journal_paper_doi               10.1039/C5SC00295H
_journal_volume                  6
_journal_year                    2015
_chemical_formula_moiety         'C24 H25 N O3'
_chemical_formula_sum            'C24 H25 N O3'
_chemical_formula_weight         375.45
_chemical_name_common            ' lm1HF1105B'
_chemical_name_systematic        4aia
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_creation_date             2014-09-23T18:51:06-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2014-12-09 deposited with the CCDC.
2015-03-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.6090(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.6584(5)
_cell_length_b                   6.7792(2)
_cell_length_c                   14.6200(4)
_cell_measurement_reflns_used    9914
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      33.05
_cell_measurement_theta_min      2.88
_cell_measurement_wavelength     0.71073
_cell_volume                     1885.39(9)
_computing_cell_refinement       'SAINT V8.34A integration software'
_computing_data_collection       'Bruker APEX2 software'
_computing_data_reduction        'SORTAV (Blessing, 1995)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'APEX-II CCD'
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       '\f or \w oscillation scans'
_diffrn_orient_matrix_UB_11      0.047173
_diffrn_orient_matrix_UB_12      0.019478
_diffrn_orient_matrix_UB_13      0.044799
_diffrn_orient_matrix_UB_21      0.008065
_diffrn_orient_matrix_UB_22      0.118199
_diffrn_orient_matrix_UB_23      -0.036818
_diffrn_orient_matrix_UB_31      -0.02175
_diffrn_orient_matrix_UB_32      0.086076
_diffrn_orient_matrix_UB_33      0.04042
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            85307
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_reduction_process
;
        Scaled and merged with Sortav
        R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
        R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.238
_diffrn_reflns_theta_min         2.141
_diffrn_source                   'sealed x-ray tube'
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.963
_exptl_absorpt_correction_T_min  0.916
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/3 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.55
_exptl_crystal_size_min          0.54
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.24
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     355
_refine_ls_number_reflns         7249
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0417
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0657P)^2^+0.3286P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1095
_refine_ls_wR_factor_ref         0.1189
_reflns_number_gt                5746
_reflns_number_total             7249
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5sc00295h2.cif
_cod_data_source_block           shelx
_cod_depositor_comments
'Adding full bibliography for 1518843--1518845.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1518845
_shelx_estimated_absorpt_t_min   0.951
_shelx_estimated_absorpt_t_max   0.955