# 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        'You, Shu-Li'
_publ_contact_author_email       slyou@mail.sioc.ac.cn

_publ_section_title              
;
N-Heterocyclic Carbene-Catalyzed Tandem Aza-Benzoin/Michael
Reactions: On Site Reversal of the Reactivity of N-Boc Imines
;
loop_
_publ_author_name
'Shu-Li You'
'Ke-Jia Wu'
'Gong-Qiang Li'
'Yi Li'
'Li-Xin Dai'

# Attachment '- cd29258.cif'

data_cd29258
_database_code_depnum_ccdc_archive 'CCDC 772193'
#TrackingRef '- cd29258.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H12 Br N O2'
_chemical_formula_weight         342.19

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.978(2)
_cell_length_b                   11.514(2)
_cell_length_c                   12.103(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 113.623(3)
_cell_angle_gamma                90.00
_cell_volume                     1529.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2053
_cell_measurement_theta_min      5.128
_cell_measurement_theta_max      50.077

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.452
_exptl_crystal_size_mid          0.380
_exptl_crystal_size_min          0.287
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    2.691
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.4856
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   sadabs

_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       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9025
_diffrn_reflns_av_R_equivalents  0.0528
_diffrn_reflns_av_sigmaI/netI    0.0747
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.02
_diffrn_reflns_theta_max         27.50
_reflns_number_total             3484
_reflns_number_gt                1884
_reflns_threshold_expression     >2sigma(I)

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

_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^)+(0.0629P)^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     SHELXL
_refine_ls_extinction_coef       0.0289(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         3484
_refine_ls_number_parameters     195
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0901
_refine_ls_R_factor_gt           0.0480
_refine_ls_wR_factor_ref         0.1200
_refine_ls_wR_factor_gt          0.1108
_refine_ls_goodness_of_fit_ref   0.853
_refine_ls_restrained_S_all      0.853
_refine_ls_shift/su_max          0.001
_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
Br Br 0.88515(4) 0.90066(4) -0.24051(4) 0.0888(3) Uani 1 1 d . . .
O1 O 0.57270(17) 0.45905(17) 0.16122(16) 0.0398(5) Uani 1 1 d . . .
O2 O 0.4532(2) 0.8523(2) -0.0202(2) 0.0629(7) Uani 1 1 d . . .
N1 N 0.5821(2) 0.6286(2) 0.0687(2) 0.0344(6) Uani 1 1 d D . .
C1 C 0.6137(2) 0.5574(3) 0.1632(2) 0.0332(6) Uani 1 1 d . . .
C2 C 0.7065(3) 0.6161(2) 0.2708(3) 0.0403(7) Uani 1 1 d . . .
H2A H 0.7846 0.5771 0.2958 0.048 Uiso 1 1 calc R . .
H2B H 0.6811 0.6153 0.3375 0.048 Uiso 1 1 calc R . .
C3 C 0.7157(2) 0.7410(2) 0.2317(2) 0.0322(7) Uani 1 1 d . . .
H3 H 0.8007 0.7613 0.2495 0.039 Uiso 1 1 calc R . .
C4 C 0.6376(2) 0.7429(2) 0.0925(2) 0.0325(7) Uani 1 1 d . . .
C5 C 0.5359(3) 0.8327(2) 0.0756(3) 0.0396(7) Uani 1 1 d . . .
C6 C 0.5578(3) 0.8827(2) 0.1931(3) 0.0400(7) Uani 1 1 d . . .
C7 C 0.6582(3) 0.8303(2) 0.2819(3) 0.0362(7) Uani 1 1 d . . .
C8 C 0.6940(3) 0.8650(3) 0.4000(3) 0.0567(9) Uani 1 1 d . . .
H8 H 0.7603 0.8301 0.4608 0.068 Uiso 1 1 calc R . .
C9 C 0.6304(4) 0.9520(4) 0.4267(4) 0.0825(13) Uani 1 1 d . . .
H9 H 0.6555 0.9773 0.5060 0.099 Uiso 1 1 calc R . .
C10 C 0.5289(4) 1.0031(4) 0.3372(4) 0.0833(13) Uani 1 1 d . . .
H10 H 0.4863 1.0609 0.3575 0.100 Uiso 1 1 calc R . .
C11 C 0.4917(3) 0.9690(3) 0.2201(3) 0.0629(10) Uani 1 1 d . . .
H11 H 0.4239 1.0025 0.1599 0.075 Uiso 1 1 calc R . .
C12 C 0.7035(2) 0.7740(2) 0.0135(3) 0.0336(7) Uani 1 1 d . . .
C13 C 0.6693(3) 0.7282(3) -0.1005(3) 0.0525(9) Uani 1 1 d . . .
H13 H 0.6088 0.6717 -0.1269 0.063 Uiso 1 1 calc R . .
C14 C 0.7232(3) 0.7646(3) -0.1764(3) 0.0620(10) Uani 1 1 d . . .
H14 H 0.6988 0.7334 -0.2534 0.074 Uiso 1 1 calc R . .
C15 C 0.8126(3) 0.8468(3) -0.1370(3) 0.0533(9) Uani 1 1 d . . .
C16 C 0.8486(3) 0.8932(3) -0.0246(3) 0.0637(10) Uani 1 1 d . . .
H16 H 0.9093 0.9495 0.0015 0.076 Uiso 1 1 calc R . .
C17 C 0.7939(3) 0.8558(3) 0.0507(3) 0.0541(9) Uani 1 1 d . . .
H17 H 0.8192 0.8869 0.1279 0.065 Uiso 1 1 calc R . .
H1 H 0.533(2) 0.609(2) -0.0011(18) 0.041(9) Uiso 1 1 d 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
Br 0.0787(4) 0.1365(5) 0.0661(3) 0.0174(3) 0.0448(3) -0.0119(3)
O1 0.0429(12) 0.0370(12) 0.0269(11) 0.0001(9) 0.0009(9) -0.0090(10)
O2 0.0507(14) 0.0769(16) 0.0376(14) 0.0050(12) -0.0068(12) 0.0175(13)
N1 0.0342(14) 0.0376(14) 0.0172(12) -0.0021(11) -0.0044(11) -0.0116(11)
C1 0.0267(15) 0.0378(17) 0.0266(15) -0.0020(13) 0.0019(12) -0.0009(13)
C2 0.0410(18) 0.0404(17) 0.0241(15) -0.0006(13) -0.0031(13) -0.0003(14)
C3 0.0264(15) 0.0397(17) 0.0219(14) -0.0015(12) 0.0006(12) -0.0054(12)
C4 0.0312(16) 0.0332(16) 0.0238(15) -0.0024(12) 0.0013(12) -0.0052(12)
C5 0.0329(17) 0.0418(18) 0.0361(18) 0.0070(14) 0.0054(14) -0.0012(14)
C6 0.0422(18) 0.0404(17) 0.0376(17) 0.0043(15) 0.0164(15) 0.0031(14)
C7 0.0381(16) 0.0378(17) 0.0303(16) -0.0013(14) 0.0111(13) -0.0047(14)
C8 0.066(2) 0.069(2) 0.0285(17) -0.0050(17) 0.0117(16) 0.0076(19)
C9 0.111(4) 0.092(3) 0.048(2) -0.015(2) 0.035(3) 0.021(3)
C10 0.103(3) 0.091(3) 0.065(3) -0.004(2) 0.043(3) 0.039(3)
C11 0.064(2) 0.069(2) 0.058(2) 0.010(2) 0.0262(19) 0.022(2)
C12 0.0332(16) 0.0338(15) 0.0271(15) 0.0009(13) 0.0049(13) -0.0015(13)
C13 0.062(2) 0.059(2) 0.0330(18) -0.0100(16) 0.0155(16) -0.0221(17)
C14 0.079(3) 0.074(2) 0.0345(19) -0.0098(18) 0.0247(19) -0.014(2)
C15 0.052(2) 0.068(2) 0.045(2) 0.0050(18) 0.0246(17) -0.0109(19)
C16 0.059(2) 0.080(3) 0.054(2) -0.011(2) 0.0249(19) -0.0325(19)
C17 0.060(2) 0.061(2) 0.0394(19) -0.0151(17) 0.0186(17) -0.0237(18)

_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
Br C15 1.893(3) . ?
O1 C1 1.231(3) . ?
O2 C5 1.207(3) . ?
N1 C1 1.332(4) . ?
N1 C4 1.449(3) . ?
N1 H1 0.846(17) . ?
C1 C2 1.492(4) . ?
C2 C3 1.532(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C7 1.495(4) . ?
C3 C4 1.566(4) . ?
C3 H3 0.9800 . ?
C4 C12 1.507(4) . ?
C4 C5 1.547(4) . ?
C5 C6 1.458(4) . ?
C6 C11 1.388(4) . ?
C6 C7 1.390(4) . ?
C7 C8 1.377(4) . ?
C8 C9 1.373(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.394(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.362(5) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C17 1.368(4) . ?
C12 C13 1.378(4) . ?
C13 C14 1.382(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.364(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.361(5) . ?
C16 C17 1.387(4) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?

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
C1 N1 C4 116.0(2) . . ?
C1 N1 H1 122.4(19) . . ?
C4 N1 H1 121.6(19) . . ?
O1 C1 N1 125.1(2) . . ?
O1 C1 C2 125.8(3) . . ?
N1 C1 C2 109.1(2) . . ?
C1 C2 C3 106.0(2) . . ?
C1 C2 H2A 110.5 . . ?
C3 C2 H2A 110.5 . . ?
C1 C2 H2B 110.5 . . ?
C3 C2 H2B 110.5 . . ?
H2A C2 H2B 108.7 . . ?
C7 C3 C2 114.7(2) . . ?
C7 C3 C4 104.7(2) . . ?
C2 C3 C4 105.0(2) . . ?
C7 C3 H3 110.7 . . ?
C2 C3 H3 110.7 . . ?
C4 C3 H3 110.7 . . ?
N1 C4 C12 113.9(2) . . ?
N1 C4 C5 107.8(2) . . ?
C12 C4 C5 110.0(2) . . ?
N1 C4 C3 103.3(2) . . ?
C12 C4 C3 116.5(2) . . ?
C5 C4 C3 104.5(2) . . ?
O2 C5 C6 128.3(3) . . ?
O2 C5 C4 123.5(3) . . ?
C6 C5 C4 108.1(2) . . ?
C11 C6 C7 121.9(3) . . ?
C11 C6 C5 128.0(3) . . ?
C7 C6 C5 110.1(3) . . ?
C8 C7 C6 119.3(3) . . ?
C8 C7 C3 128.3(3) . . ?
C6 C7 C3 112.4(3) . . ?
C9 C8 C7 119.0(3) . . ?
C9 C8 H8 120.5 . . ?
C7 C8 H8 120.5 . . ?
C8 C9 C10 121.2(4) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
C11 C10 C9 120.5(3) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C6 118.1(3) . . ?
C10 C11 H11 120.9 . . ?
C6 C11 H11 120.9 . . ?
C17 C12 C13 118.1(3) . . ?
C17 C12 C4 120.1(3) . . ?
C13 C12 C4 121.6(3) . . ?
C12 C13 C14 121.3(3) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 H13 119.4 . . ?
C15 C14 C13 119.2(3) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C16 C15 C14 120.8(3) . . ?
C16 C15 Br 119.2(3) . . ?
C14 C15 Br 120.0(3) . . ?
C15 C16 C17 119.4(3) . . ?
C15 C16 H16 120.3 . . ?
C17 C16 H16 120.3 . . ?
C12 C17 C16 121.2(3) . . ?
C12 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?

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
C4 N1 C1 O1 177.2(3) . . . . ?
C4 N1 C1 C2 -2.9(3) . . . . ?
O1 C1 C2 C3 -173.2(3) . . . . ?
N1 C1 C2 C3 6.9(3) . . . . ?
C1 C2 C3 C7 106.4(3) . . . . ?
C1 C2 C3 C4 -7.9(3) . . . . ?
C1 N1 C4 C12 125.1(3) . . . . ?
C1 N1 C4 C5 -112.5(3) . . . . ?
C1 N1 C4 C3 -2.3(3) . . . . ?
C7 C3 C4 N1 -114.9(2) . . . . ?
C2 C3 C4 N1 6.2(3) . . . . ?
C7 C3 C4 C12 119.4(2) . . . . ?
C2 C3 C4 C12 -119.4(3) . . . . ?
C7 C3 C4 C5 -2.2(3) . . . . ?
C2 C3 C4 C5 119.0(2) . . . . ?
N1 C4 C5 O2 -65.9(4) . . . . ?
C12 C4 C5 O2 58.8(4) . . . . ?
C3 C4 C5 O2 -175.4(3) . . . . ?
N1 C4 C5 C6 112.5(2) . . . . ?
C12 C4 C5 C6 -122.8(2) . . . . ?
C3 C4 C5 C6 3.0(3) . . . . ?
O2 C5 C6 C11 -3.7(5) . . . . ?
C4 C5 C6 C11 178.0(3) . . . . ?
O2 C5 C6 C7 175.5(3) . . . . ?
C4 C5 C6 C7 -2.8(3) . . . . ?
C11 C6 C7 C8 -0.4(5) . . . . ?
C5 C6 C7 C8 -179.7(3) . . . . ?
C11 C6 C7 C3 -179.4(3) . . . . ?
C5 C6 C7 C3 1.3(3) . . . . ?
C2 C3 C7 C8 67.3(4) . . . . ?
C4 C3 C7 C8 -178.2(3) . . . . ?
C2 C3 C7 C6 -113.9(3) . . . . ?
C4 C3 C7 C6 0.6(3) . . . . ?
C6 C7 C8 C9 -1.0(5) . . . . ?
C3 C7 C8 C9 177.8(3) . . . . ?
C7 C8 C9 C10 1.8(6) . . . . ?
C8 C9 C10 C11 -1.2(7) . . . . ?
C9 C10 C11 C6 -0.2(6) . . . . ?
C7 C6 C11 C10 1.0(5) . . . . ?
C5 C6 C11 C10 -179.8(3) . . . . ?
N1 C4 C12 C17 -156.6(3) . . . . ?
C5 C4 C12 C17 82.2(3) . . . . ?
C3 C4 C12 C17 -36.5(4) . . . . ?
N1 C4 C12 C13 28.1(4) . . . . ?
C5 C4 C12 C13 -93.1(3) . . . . ?
C3 C4 C12 C13 148.3(3) . . . . ?
C17 C12 C13 C14 -0.9(5) . . . . ?
C4 C12 C13 C14 174.4(3) . . . . ?
C12 C13 C14 C15 0.5(5) . . . . ?
C13 C14 C15 C16 -0.2(6) . . . . ?
C13 C14 C15 Br -178.5(3) . . . . ?
C14 C15 C16 C17 0.3(6) . . . . ?
Br C15 C16 C17 178.6(3) . . . . ?
C13 C12 C17 C16 1.0(5) . . . . ?
C4 C12 C17 C16 -174.4(3) . . . . ?
C15 C16 C17 C12 -0.7(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 0.846(17) 2.000(18) 2.840(3) 172(3) 3_665

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.548
_refine_diff_density_min         -0.541
_refine_diff_density_rms         0.065