Chiral Gold Complex-Catalyzed Hetero-Diels-Alder Reaction of Diazenes: Highly Enantioselective and General for Dienes
Bin Liu; Kang-Nan Li; Shi-Wei Luo; Jian-Zhou Huang; Huan Pang; Liu-Zhu Gong; Journal of the American Chemical Society 135 (2013) 3323–3326; doi:10.1021/ja3110472

data_4119404
_publ_section_title
;
 Chiral Gold Complex-Catalyzed Hetero-Diels-Alder Reaction of Diazenes:
 Highly Enantioselective and General for Dienes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3323
_journal_page_last               3326
_journal_paper_doi               10.1021/ja3110472
_journal_volume                  135
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_sum            'C15 H20 Cl N3 O2'
_chemical_formula_weight         309.79
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.43700(10)
_cell_length_b                   8.4944(3)
_cell_length_c                   34.8951(10)
_cell_measurement_reflns_used    5606
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      69.9037
_cell_measurement_theta_min      3.7970
_cell_volume                     1611.60(8)
_computing_cell_refinement       'CrysAlisPro (Oxford Diffraction Ltd.)'
_computing_data_collection       'CrysAlisPro (Oxford Diffraction Ltd.)'
_computing_data_reduction        'CrysAlisPro (Oxford Diffraction Ltd.)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      290(2)
_diffrn_detector_area_resol_mean 15.9149
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Gemini S Ultra, Oxford Diffraction'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'Enhance Ultra (Cu) x-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_sigmaI/netI    0.0211
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            11726
_diffrn_reflns_theta_full        70.03
_diffrn_reflns_theta_max         70.03
_diffrn_reflns_theta_min         5.07
_exptl_absorpt_coefficient_mu    2.166
_exptl_absorpt_correction_T_max  0.5532
_exptl_absorpt_correction_T_min  0.5093
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.31
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.024(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3017
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0367
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0498P)^2^+0.1507P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0915
_refine_ls_wR_factor_ref         0.0963
_reflns_number_gt                2721
_reflns_number_total             3017
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja3110472_si_002.cif
_cod_data_source_block           shelxl
_cod_database_code               4119404