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_4119403
_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            'C13 H14 Cl N3 O'
_chemical_formula_weight         263.72
_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                   6.3709(8)
_cell_length_b                   12.5855(16)
_cell_length_c                   16.038(2)
_cell_measurement_reflns_used    2552
_cell_measurement_temperature    140(2)
_cell_measurement_theta_max      28.74
_cell_measurement_theta_min      3.01
_cell_volume                     1285.9(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      140(2)
_diffrn_measured_fraction_theta_full 0.999
_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_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_av_sigmaI/netI    0.0443
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            11561
_diffrn_reflns_theta_full        29.10
_diffrn_reflns_theta_max         29.10
_diffrn_reflns_theta_min         2.06
_exptl_absorpt_coefficient_mu    0.289
_exptl_absorpt_correction_T_max  0.9857
_exptl_absorpt_correction_T_min  0.9446
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_description       prism
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.04(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         3451
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0370
_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^)+(0.0297P)^2^+0.1100P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0738
_refine_ls_wR_factor_ref         0.0788
_reflns_number_gt                2852
_reflns_number_total             3451
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja3110472_si_001.cif
_cod_data_source_block           mo_dm12570_0m
_cod_database_code               4119403