# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2010

data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182

_publ_contact_author_name        'Liming Zhang'
_publ_contact_author_email       ZHANG@CHEM.UCSB.EDU

_publ_section_title              
;
Efficient Synthesis of Azepan-4-ones via Two-Step [5+2]
Annulation: Gold Catalysis Involving An Unusual
1,7-Hydride Migration
;
loop_
_publ_author_name
'Liming Zhang'
'Li Cui'
'Longwu Ye'

# Attachment 'L1-corrected.CIF'

data_l1
_database_code_depnum_ccdc_archive 'CCDC 762367'
#TrackingRef 'L1-corrected.CIF'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C38 H42 N2 O2'
_chemical_formula_weight         558.74

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.7366(19)
_cell_length_b                   10.508(3)
_cell_length_c                   13.624(4)
_cell_angle_alpha                109.154(5)
_cell_angle_beta                 91.003(5)
_cell_angle_gamma                102.607(5)
_cell_volume                     753.5(4)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             300
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.320
_exptl_absorpt_correction_T_max  0.554
_exptl_absorpt_process_details   'Psi scan'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'Omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6116
_diffrn_reflns_av_R_equivalents  0.0596
_diffrn_reflns_av_sigmaI/netI    0.0747
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.59
_diffrn_reflns_theta_max         26.41
_reflns_number_total             2958
_reflns_number_gt                1789
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0524P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2958
_refine_ls_number_parameters     274
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0865
_refine_ls_R_factor_gt           0.0498
_refine_ls_wR_factor_ref         0.1170
_refine_ls_wR_factor_gt          0.1030
_refine_ls_goodness_of_fit_ref   0.914
_refine_ls_restrained_S_all      0.914
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1735(3) 0.82136(19) 0.15695(13) 0.0414(4) Uani 1 1 d . . .
C2 C 0.0238(3) 0.94875(18) 0.31834(13) 0.0383(4) Uani 1 1 d . . .
C3 C 0.2737(3) 1.0349(2) 0.36825(15) 0.0442(5) Uani 1 1 d . . .
C4 C 0.3837(4) 1.15446(19) 0.33334(14) 0.0501(5) Uani 1 1 d . . .
C5 C 0.2284(4) 1.2150(2) 0.28006(16) 0.0536(5) Uani 1 1 d . . .
C6 C 0.1545(4) 1.1209(2) 0.16668(15) 0.0533(5) Uani 1 1 d . . .
C7 C -0.0490(4) 0.99535(19) 0.15521(16) 0.0467(5) Uani 1 1 d . . .
C8 C -0.0630(3) 0.82690(17) 0.35684(12) 0.0389(4) Uani 1 1 d . . .
C9 C 0.0737(4) 0.79061(19) 0.42366(14) 0.0464(5) Uani 1 1 d . . .
C10 C -0.0182(4) 0.6776(2) 0.45424(16) 0.0550(5) Uani 1 1 d . . .
C11 C -0.2470(4) 0.6000(2) 0.42086(15) 0.0554(5) Uani 1 1 d . . .
C12 C -0.3869(4) 0.6358(2) 0.35529(16) 0.0568(6) Uani 1 1 d . . .
C13 C -0.2949(3) 0.7469(2) 0.32330(15) 0.0474(5) Uani 1 1 d . . .
C14 C 0.1033(3) 0.73233(16) 0.04380(12) 0.0379(4) Uani 1 1 d . . .
C15 C 0.2708(4) 0.7291(2) -0.02804(15) 0.0513(5) Uani 1 1 d . . .
C16 C 0.2123(4) 0.6409(2) -0.13061(16) 0.0598(6) Uani 1 1 d . . .
C17 C -0.0119(4) 0.5564(2) -0.16207(15) 0.0545(5) Uani 1 1 d . . .
C18 C -0.1819(4) 0.56028(19) -0.09133(15) 0.0498(5) Uani 1 1 d . . .
C19 C -0.1233(3) 0.64768(18) 0.01083(14) 0.0432(5) Uani 1 1 d . . .
H2 H -0.094(3) 1.0111(16) 0.3384(11) 0.037(4) Uiso 1 1 d . . .
H9 H 0.237(3) 0.8420(18) 0.4469(13) 0.054(5) Uiso 1 1 d . . .
H10 H 0.079(3) 0.6517(19) 0.4954(15) 0.057(6) Uiso 1 1 d . . .
H11 H -0.318(3) 0.5186(19) 0.4424(13) 0.055(5) Uiso 1 1 d . . .
H12 H -0.548(4) 0.583(2) 0.3343(15) 0.071(6) Uiso 1 1 d . . .
H13 H -0.401(3) 0.7724(18) 0.2755(14) 0.059(5) Uiso 1 1 d . . .
H15 H 0.431(4) 0.7919(19) -0.0036(15) 0.066(6) Uiso 1 1 d . . .
H16 H 0.338(3) 0.6430(19) -0.1796(15) 0.067(6) Uiso 1 1 d . . .
H17 H -0.056(4) 0.493(2) -0.2361(16) 0.074(6) Uiso 1 1 d . . .
H18 H -0.343(3) 0.4992(18) -0.1125(13) 0.053(5) Uiso 1 1 d . . .
H19 H -0.246(3) 0.6516(18) 0.0624(14) 0.054(5) Uiso 1 1 d . . .
H1A H 0.338(3) 0.8816(18) 0.1612(13) 0.049(5) Uiso 1 1 d . . .
H3A H 0.268(3) 1.0753(19) 0.4443(16) 0.062(6) Uiso 1 1 d . . .
H5A H 0.326(3) 1.305(2) 0.2823(14) 0.060(6) Uiso 1 1 d . . .
H6A H 0.098(3) 1.169(2) 0.1307(15) 0.063(6) Uiso 1 1 d . . .
H7A H -0.095(3) 0.9447(18) 0.0805(15) 0.052(5) Uiso 1 1 d . . .
H1B H 0.191(3) 0.7603(18) 0.1991(13) 0.050(5) Uiso 1 1 d . . .
H3B H 0.391(3) 0.9777(19) 0.3626(13) 0.052(5) Uiso 1 1 d . . .
H5B H 0.085(3) 1.2273(18) 0.3163(14) 0.055(5) Uiso 1 1 d . . .
H6B H 0.300(4) 1.091(2) 0.1316(15) 0.073(6) Uiso 1 1 d . . .
H7B H -0.196(3) 1.0260(18) 0.1879(13) 0.054(5) Uiso 1 1 d . . .
N N -0.0051(2) 0.89600(13) 0.20324(10) 0.0386(4) Uani 1 1 d . . .
O O 0.5992(3) 1.19953(17) 0.34695(12) 0.0811(5) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0430(11) 0.0446(11) 0.0376(10) 0.0119(9) 0.0029(8) 0.0157(9)
C2 0.0409(10) 0.0399(10) 0.0334(9) 0.0087(8) 0.0035(8) 0.0142(8)
C3 0.0456(11) 0.0448(11) 0.0384(11) 0.0084(9) 0.0013(9) 0.0121(9)
C4 0.0520(12) 0.0471(11) 0.0410(11) 0.0059(9) 0.0026(9) 0.0051(10)
C5 0.0613(13) 0.0408(12) 0.0558(13) 0.0145(10) 0.0058(11) 0.0089(11)
C6 0.0738(15) 0.0463(12) 0.0467(12) 0.0211(10) 0.0072(11) 0.0197(11)
C7 0.0577(13) 0.0459(11) 0.0386(11) 0.0123(9) -0.0008(10) 0.0202(10)
C8 0.0432(10) 0.0409(10) 0.0314(9) 0.0075(8) 0.0061(8) 0.0148(8)
C9 0.0459(11) 0.0519(12) 0.0409(11) 0.0148(9) 0.0002(9) 0.0120(10)
C10 0.0662(14) 0.0622(13) 0.0448(12) 0.0238(10) 0.0050(10) 0.0234(12)
C11 0.0654(14) 0.0503(12) 0.0520(13) 0.0208(10) 0.0117(11) 0.0106(11)
C12 0.0508(13) 0.0542(13) 0.0594(13) 0.0165(11) 0.0052(10) 0.0047(11)
C13 0.0450(11) 0.0518(11) 0.0455(11) 0.0157(9) 0.0004(9) 0.0136(10)
C14 0.0440(10) 0.0360(9) 0.0361(10) 0.0112(8) 0.0040(8) 0.0161(8)
C15 0.0480(12) 0.0550(12) 0.0475(12) 0.0117(10) 0.0083(10) 0.0141(10)
C16 0.0630(14) 0.0689(14) 0.0480(12) 0.0140(11) 0.0197(11) 0.0245(12)
C17 0.0747(15) 0.0488(12) 0.0377(12) 0.0057(10) 0.0024(11) 0.0243(11)
C18 0.0549(13) 0.0376(10) 0.0520(12) 0.0100(9) -0.0039(10) 0.0096(10)
C19 0.0469(11) 0.0409(10) 0.0427(11) 0.0140(9) 0.0073(9) 0.0127(9)
N 0.0449(8) 0.0398(8) 0.0328(8) 0.0102(6) 0.0030(6) 0.0171(7)
O 0.0520(9) 0.0927(12) 0.0942(12) 0.0421(10) -0.0052(8) -0.0069(9)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N 1.453(2) . ?
C1 C14 1.510(2) . ?
C1 H1A 1.003(17) . ?
C1 H1B 1.010(18) . ?
C2 N 1.474(2) . ?
C2 C3 1.527(2) . ?
C2 C8 1.528(2) . ?
C2 H2 1.019(16) . ?
C3 C4 1.503(3) . ?
C3 H3A 0.987(19) . ?
C3 H3B 0.98(2) . ?
C4 O 1.211(2) . ?
C4 C5 1.501(3) . ?
C5 C6 1.528(3) . ?
C5 H5A 0.976(19) . ?
C5 H5B 0.980(19) . ?
C6 C7 1.521(3) . ?
C6 H6A 0.91(2) . ?
C6 H6B 1.02(2) . ?
C7 N 1.463(2) . ?
C7 H7A 0.981(18) . ?
C7 H7B 1.024(19) . ?
C8 C9 1.387(2) . ?
C8 C13 1.387(2) . ?
C9 C10 1.386(3) . ?
C9 H9 0.960(18) . ?
C10 C11 1.365(3) . ?
C10 H10 0.92(2) . ?
C11 C12 1.383(3) . ?
C11 H11 1.001(18) . ?
C12 C13 1.380(3) . ?
C12 H12 0.95(2) . ?
C13 H13 1.020(19) . ?
C14 C19 1.377(2) . ?
C14 C15 1.381(2) . ?
C15 C16 1.386(3) . ?
C15 H15 0.983(19) . ?
C16 C17 1.363(3) . ?
C16 H16 0.99(2) . ?
C17 C18 1.380(3) . ?
C17 H17 1.00(2) . ?
C18 C19 1.380(3) . ?
C18 H18 0.981(17) . ?
C19 H19 0.999(18) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N C1 C14 113.26(14) . . ?
N C1 H1A 114.6(10) . . ?
C14 C1 H1A 107.3(10) . . ?
N C1 H1B 106.4(10) . . ?
C14 C1 H1B 109.2(9) . . ?
H1A C1 H1B 105.8(13) . . ?
N C2 C3 115.49(14) . . ?
N C2 C8 108.43(13) . . ?
C3 C2 C8 112.55(15) . . ?
N C2 H2 104.2(8) . . ?
C3 C2 H2 108.2(8) . . ?
C8 C2 H2 107.4(8) . . ?
C4 C3 C2 117.66(16) . . ?
C4 C3 H3A 105.7(10) . . ?
C2 C3 H3A 108.9(11) . . ?
C4 C3 H3B 107.8(10) . . ?
C2 C3 H3B 112.5(10) . . ?
H3A C3 H3B 103.1(15) . . ?
O C4 C5 120.47(18) . . ?
O C4 C3 119.22(19) . . ?
C5 C4 C3 120.29(18) . . ?
C4 C5 C6 110.27(17) . . ?
C4 C5 H5A 106.4(11) . . ?
C6 C5 H5A 109.8(11) . . ?
C4 C5 H5B 110.8(10) . . ?
C6 C5 H5B 109.5(10) . . ?
H5A C5 H5B 110.0(15) . . ?
C7 C6 C5 113.16(17) . . ?
C7 C6 H6A 105.8(12) . . ?
C5 C6 H6A 109.0(12) . . ?
C7 C6 H6B 111.0(11) . . ?
C5 C6 H6B 110.6(11) . . ?
H6A C6 H6B 107.0(16) . . ?
N C7 C6 117.60(17) . . ?
N C7 H7A 107.6(10) . . ?
C6 C7 H7A 108.2(10) . . ?
N C7 H7B 104.5(9) . . ?
C6 C7 H7B 110.5(9) . . ?
H7A C7 H7B 108.1(14) . . ?
C9 C8 C13 117.39(17) . . ?
C9 C8 C2 124.54(16) . . ?
C13 C8 C2 118.06(16) . . ?
C10 C9 C8 120.93(19) . . ?
C10 C9 H9 119.3(11) . . ?
C8 C9 H9 119.7(11) . . ?
C11 C10 C9 121.0(2) . . ?
C11 C10 H10 119.2(11) . . ?
C9 C10 H10 119.7(11) . . ?
C10 C11 C12 118.8(2) . . ?
C10 C11 H11 122.5(10) . . ?
C12 C11 H11 118.6(10) . . ?
C13 C12 C11 120.4(2) . . ?
C13 C12 H12 121.6(12) . . ?
C11 C12 H12 118.1(12) . . ?
C12 C13 C8 121.47(19) . . ?
C12 C13 H13 119.3(10) . . ?
C8 C13 H13 119.2(10) . . ?
C19 C14 C15 118.51(16) . . ?
C19 C14 C1 121.24(16) . . ?
C15 C14 C1 120.17(16) . . ?
C14 C15 C16 120.56(19) . . ?
C14 C15 H15 117.5(11) . . ?
C16 C15 H15 122.0(11) . . ?
C17 C16 C15 120.4(2) . . ?
C17 C16 H16 121.9(11) . . ?
C15 C16 H16 117.7(11) . . ?
C16 C17 C18 119.55(19) . . ?
C16 C17 H17 121.0(11) . . ?
C18 C17 H17 119.5(11) . . ?
C19 C18 C17 120.02(19) . . ?
C19 C18 H18 119.4(10) . . ?
C17 C18 H18 120.6(10) . . ?
C14 C19 C18 120.94(18) . . ?
C14 C19 H19 118.5(10) . . ?
C18 C19 H19 120.5(10) . . ?
C1 N C7 114.60(14) . . ?
C1 N C2 113.59(13) . . ?
C7 N C2 114.83(13) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N C2 C3 C4 52.2(2) . . . . ?
C8 C2 C3 C4 177.50(15) . . . . ?
C2 C3 C4 O -159.13(18) . . . . ?
C2 C3 C4 C5 19.5(3) . . . . ?
O C4 C5 C6 101.9(2) . . . . ?
C3 C4 C5 C6 -76.7(2) . . . . ?
C4 C5 C6 C7 78.6(2) . . . . ?
C5 C6 C7 N -62.5(2) . . . . ?
N C2 C8 C9 124.50(17) . . . . ?
C3 C2 C8 C9 -4.5(2) . . . . ?
N C2 C8 C13 -55.78(19) . . . . ?
C3 C2 C8 C13 175.20(16) . . . . ?
C13 C8 C9 C10 0.8(3) . . . . ?
C2 C8 C9 C10 -179.46(16) . . . . ?
C8 C9 C10 C11 -1.1(3) . . . . ?
C9 C10 C11 C12 0.2(3) . . . . ?
C10 C11 C12 C13 0.9(3) . . . . ?
C11 C12 C13 C8 -1.1(3) . . . . ?
C9 C8 C13 C12 0.2(3) . . . . ?
C2 C8 C13 C12 -179.51(16) . . . . ?
N C1 C14 C19 -46.1(2) . . . . ?
N C1 C14 C15 137.29(17) . . . . ?
C19 C14 C15 C16 -1.0(3) . . . . ?
C1 C14 C15 C16 175.77(17) . . . . ?
C14 C15 C16 C17 0.3(3) . . . . ?
C15 C16 C17 C18 0.7(3) . . . . ?
C16 C17 C18 C19 -1.0(3) . . . . ?
C15 C14 C19 C18 0.7(3) . . . . ?
C1 C14 C19 C18 -175.98(16) . . . . ?
C17 C18 C19 C14 0.2(3) . . . . ?
C14 C1 N C7 -62.48(19) . . . . ?
C14 C1 N C2 162.78(14) . . . . ?
C6 C7 N C1 -66.2(2) . . . . ?
C6 C7 N C2 67.9(2) . . . . ?
C3 C2 N C1 52.4(2) . . . . ?
C8 C2 N C1 -75.00(17) . . . . ?
C3 C2 N C7 -82.3(2) . . . . ?
C8 C2 N C7 150.37(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.955
_diffrn_reflns_theta_full        26.41
_diffrn_measured_fraction_theta_full 0.955
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.060