# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is (c) The Royal Society of Chemistry 2009

data_global
_journal_name_full               Org.Biomol.Chem.

_journal_coden_Cambridge         0177

_publ_contact_author_name        'Wenhao Hu'
_publ_contact_author_email       WHU@CHEM.ECNU.EDU.CN

_publ_section_title              
;
Component match in rhodium catalyzed three-component
reactions of ethyl diazoacetate, H2O and aryl imines: diastereoselective
one-step synthesis of ?-aryl isoserine derivatives
;
loop_
_publ_author_name
'Wenhao Hu'
'Zhenqiu Guo'
'Jun Jiang'
'Taoda Shi'
'Liping Yang'

# Attachment 'compound4K.cif'

data_z
_database_code_depnum_ccdc_archive 'CCDC 725598'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H17 Br Cl N O3'
_chemical_formula_weight         398.68

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'
Cl Cl 0.1484 0.1585 '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           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   8.8875(3)
_cell_length_b                   9.6663(3)
_cell_length_c                   11.1750(3)
_cell_angle_alpha                84.7920(10)
_cell_angle_beta                 76.1370(10)
_cell_angle_gamma                67.1100(10)
_cell_volume                     858.67(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.728
_exptl_crystal_size_mid          0.477
_exptl_crystal_size_min          0.134
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             404
_exptl_absorpt_coefficient_mu    2.562
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.512079
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      296(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11714
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_av_sigmaI/netI    0.0220
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.88
_diffrn_reflns_theta_max         25.01
_reflns_number_total             3017
_reflns_number_gt                2783
_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^)+(0.0416P)^2^+0.5603P] 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         3017
_refine_ls_number_parameters     212
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0337
_refine_ls_R_factor_gt           0.0308
_refine_ls_wR_factor_ref         0.0836
_refine_ls_wR_factor_gt          0.0811
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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
N1 N 0.6395(2) 0.8248(2) 0.30072(18) 0.0403(4) Uani 1 1 d . . .
H1A H 0.5847 0.9017 0.3484 0.048 Uiso 1 1 calc R . .
Br1 Br 0.30487(4) 0.37890(3) 0.09028(3) 0.05626(12) Uani 1 1 d . . .
Cl1 Cl 0.98873(11) 0.93600(9) -0.19723(6) 0.0657(2) Uani 1 1 d . . .
C1 C 0.4102(3) 0.4710(3) 0.1683(2) 0.0409(5) Uani 1 1 d . . .
C2 C 0.3326(3) 0.6220(3) 0.1957(2) 0.0480(6) Uani 1 1 d . . .
H2A H 0.2298 0.6782 0.1763 0.058 Uiso 1 1 calc R . .
C3 C 0.4092(3) 0.6891(3) 0.2523(2) 0.0455(6) Uani 1 1 d . . .
H3A H 0.3572 0.7911 0.2708 0.055 Uiso 1 1 calc R . .
C4 C 0.5625(3) 0.6067(2) 0.2819(2) 0.0355(5) Uani 1 1 d . . .
C5 C 0.6380(3) 0.4558(3) 0.2521(2) 0.0404(5) Uani 1 1 d . . .
H5A H 0.7413 0.3993 0.2707 0.048 Uiso 1 1 calc R . .
C6 C 0.5630(3) 0.3868(3) 0.1950(2) 0.0444(5) Uani 1 1 d . . .
H6A H 0.6154 0.2852 0.1750 0.053 Uiso 1 1 calc R . .
C7 C 0.7200(3) 0.8441(2) 0.1809(2) 0.0359(5) Uani 1 1 d . . .
C8 C 0.8724(3) 0.7383(3) 0.1215(2) 0.0454(6) Uani 1 1 d . . .
H8A H 0.9198 0.6474 0.1601 0.055 Uiso 1 1 calc R . .
C9 C 0.9543(3) 0.7663(3) 0.0059(2) 0.0483(6) Uani 1 1 d . . .
H9A H 1.0567 0.6951 -0.0324 0.058 Uiso 1 1 calc R . .
C10 C 0.8842(3) 0.8988(3) -0.0519(2) 0.0451(6) Uani 1 1 d . . .
C11 C 0.7314(4) 1.0041(3) 0.0030(2) 0.0499(6) Uani 1 1 d . . .
H11A H 0.6837 1.0935 -0.0373 0.060 Uiso 1 1 calc R . .
C12 C 0.6498(3) 0.9759(3) 0.1179(2) 0.0454(6) Uani 1 1 d . . .
H12A H 0.5457 1.0464 0.1543 0.055 Uiso 1 1 calc R . .
C13 C 0.6461(3) 0.6781(2) 0.3468(2) 0.0359(5) Uani 1 1 d . . .
H13A H 0.7645 0.6115 0.3352 0.043 Uiso 1 1 calc R . .
C14 C 0.5706(3) 0.6937(3) 0.4867(2) 0.0424(5) Uani 1 1 d . . .
H14A H 0.5771 0.5949 0.5205 0.051 Uiso 1 1 calc R . .
C15 C 0.6695(3) 0.7509(3) 0.5481(2) 0.0421(5) Uani 1 1 d . . .
C16 C 0.9390(4) 0.7060(4) 0.5783(4) 0.0764(10) Uani 1 1 d . . .
H16A H 0.8788 0.7656 0.6526 0.092 Uiso 1 1 calc R . .
H16B H 1.0300 0.6188 0.5989 0.092 Uiso 1 1 calc R . .
C17 C 1.0062(7) 0.7932(9) 0.4872(5) 0.157(3) Uani 1 1 d . . .
H17A H 1.0801 0.8238 0.5185 0.236 Uiso 1 1 calc R . .
H17B H 0.9164 0.8805 0.4678 0.236 Uiso 1 1 calc R . .
H17C H 1.0673 0.7338 0.4141 0.236 Uiso 1 1 calc R . .
O1 O 0.4018(2) 0.7934(3) 0.51084(19) 0.0585(5) Uani 1 1 d . . .
O2 O 0.6098(3) 0.8670(2) 0.60386(19) 0.0631(5) Uani 1 1 d . . .
O3 O 0.8262(2) 0.6574(2) 0.5342(2) 0.0597(5) Uani 1 1 d . . .
H1B H 0.404(7) 0.863(6) 0.538(5) 0.13(2) Uiso 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
N1 0.0447(11) 0.0317(9) 0.0417(11) -0.0073(8) -0.0045(9) -0.0130(8)
Br1 0.0656(2) 0.05559(18) 0.0613(2) -0.00659(13) -0.02574(14) -0.02942(14)
Cl1 0.0845(5) 0.0763(5) 0.0401(4) 0.0010(3) -0.0038(3) -0.0407(4)
C1 0.0491(13) 0.0439(13) 0.0369(12) -0.0028(10) -0.0117(10) -0.0235(11)
C2 0.0451(14) 0.0456(13) 0.0554(15) -0.0022(11) -0.0203(12) -0.0138(11)
C3 0.0476(14) 0.0348(12) 0.0534(15) -0.0059(10) -0.0179(11) -0.0097(10)
C4 0.0399(12) 0.0348(11) 0.0321(11) -0.0007(9) -0.0070(9) -0.0151(9)
C5 0.0406(12) 0.0363(12) 0.0424(13) -0.0015(9) -0.0136(10) -0.0098(10)
C6 0.0509(14) 0.0342(11) 0.0487(14) -0.0048(10) -0.0127(11) -0.0149(10)
C7 0.0390(12) 0.0350(11) 0.0393(12) -0.0059(9) -0.0098(9) -0.0179(10)
C8 0.0431(13) 0.0401(12) 0.0485(14) 0.0010(10) -0.0093(11) -0.0117(11)
C9 0.0415(13) 0.0494(14) 0.0503(15) -0.0068(11) -0.0061(11) -0.0142(11)
C10 0.0574(15) 0.0517(14) 0.0355(12) -0.0032(10) -0.0092(11) -0.0308(12)
C11 0.0627(16) 0.0402(13) 0.0470(14) 0.0034(11) -0.0173(12) -0.0176(12)
C12 0.0452(13) 0.0363(12) 0.0498(14) -0.0060(10) -0.0088(11) -0.0099(10)
C13 0.0364(11) 0.0341(11) 0.0364(12) -0.0035(9) -0.0075(9) -0.0121(9)
C14 0.0429(13) 0.0460(13) 0.0395(12) -0.0023(10) -0.0089(10) -0.0178(11)
C15 0.0480(14) 0.0391(12) 0.0374(12) -0.0038(10) -0.0117(10) -0.0124(11)
C16 0.0612(19) 0.074(2) 0.101(3) -0.0262(19) -0.0453(19) -0.0105(16)
C17 0.133(4) 0.318(9) 0.092(3) -0.016(4) -0.007(3) -0.168(6)
O1 0.0390(10) 0.0784(14) 0.0511(11) -0.0112(10) -0.0039(8) -0.0160(10)
O2 0.0634(12) 0.0556(11) 0.0627(12) -0.0259(10) -0.0155(10) -0.0080(9)
O3 0.0505(11) 0.0498(10) 0.0791(14) -0.0202(9) -0.0313(10) -0.0052(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
N1 C7 1.393(3) . ?
N1 C13 1.448(3) . ?
N1 H1A 0.8600 . ?
Br1 C1 1.900(2) . ?
Cl1 C10 1.750(2) . ?
C1 C6 1.373(4) . ?
C1 C2 1.377(4) . ?
C2 C3 1.381(3) . ?
C2 H2A 0.9300 . ?
C3 C4 1.387(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.382(3) . ?
C4 C13 1.518(3) . ?
C5 C6 1.387(3) . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9300 . ?
C7 C8 1.391(3) . ?
C7 C12 1.392(3) . ?
C8 C9 1.382(4) . ?
C8 H8A 0.9300 . ?
C9 C10 1.367(4) . ?
C9 H9A 0.9300 . ?
C10 C11 1.376(4) . ?
C11 C12 1.377(4) . ?
C11 H11A 0.9300 . ?
C12 H12A 0.9300 . ?
C13 C14 1.542(3) . ?
C13 H13A 0.9800 . ?
C14 O1 1.408(3) . ?
C14 C15 1.511(3) . ?
C14 H14A 0.9800 . ?
C15 O2 1.198(3) . ?
C15 O3 1.313(3) . ?
C16 C17 1.432(6) . ?
C16 O3 1.454(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
O1 H1B 0.77(5) . ?

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
C7 N1 C13 121.48(18) . . ?
C7 N1 H1A 119.3 . . ?
C13 N1 H1A 119.3 . . ?
C6 C1 C2 121.1(2) . . ?
C6 C1 Br1 119.64(18) . . ?
C2 C1 Br1 119.25(19) . . ?
C1 C2 C3 119.3(2) . . ?
C1 C2 H2A 120.4 . . ?
C3 C2 H2A 120.4 . . ?
C2 C3 C4 121.0(2) . . ?
C2 C3 H3A 119.5 . . ?
C4 C3 H3A 119.5 . . ?
C5 C4 C3 118.3(2) . . ?
C5 C4 C13 120.1(2) . . ?
C3 C4 C13 121.6(2) . . ?
C4 C5 C6 121.4(2) . . ?
C4 C5 H5A 119.3 . . ?
C6 C5 H5A 119.3 . . ?
C1 C6 C5 118.9(2) . . ?
C1 C6 H6A 120.6 . . ?
C5 C6 H6A 120.6 . . ?
C8 C7 C12 117.8(2) . . ?
C8 C7 N1 122.6(2) . . ?
C12 C7 N1 119.5(2) . . ?
C9 C8 C7 120.9(2) . . ?
C9 C8 H8A 119.6 . . ?
C7 C8 H8A 119.6 . . ?
C10 C9 C8 119.8(2) . . ?
C10 C9 H9A 120.1 . . ?
C8 C9 H9A 120.1 . . ?
C9 C10 C11 120.7(2) . . ?
C9 C10 Cl1 120.0(2) . . ?
C11 C10 Cl1 119.3(2) . . ?
C10 C11 C12 119.4(2) . . ?
C10 C11 H11A 120.3 . . ?
C12 C11 H11A 120.3 . . ?
C11 C12 C7 121.3(2) . . ?
C11 C12 H12A 119.4 . . ?
C7 C12 H12A 119.4 . . ?
N1 C13 C4 114.59(19) . . ?
N1 C13 C14 107.48(18) . . ?
C4 C13 C14 111.88(18) . . ?
N1 C13 H13A 107.5 . . ?
C4 C13 H13A 107.5 . . ?
C14 C13 H13A 107.5 . . ?
O1 C14 C15 109.5(2) . . ?
O1 C14 C13 110.8(2) . . ?
C15 C14 C13 109.58(19) . . ?
O1 C14 H14A 109.0 . . ?
C15 C14 H14A 109.0 . . ?
C13 C14 H14A 109.0 . . ?
O2 C15 O3 124.7(2) . . ?
O2 C15 C14 123.4(2) . . ?
O3 C15 C14 111.9(2) . . ?
C17 C16 O3 111.1(3) . . ?
C17 C16 H16A 109.4 . . ?
O3 C16 H16A 109.4 . . ?
C17 C16 H16B 109.4 . . ?
O3 C16 H16B 109.4 . . ?
H16A C16 H16B 108.0 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C14 O1 H1B 103(4) . . ?
C15 O3 C16 117.3(2) . . ?

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
C6 C1 C2 C3 -0.8(4) . . . . ?
Br1 C1 C2 C3 -179.9(2) . . . . ?
C1 C2 C3 C4 -0.1(4) . . . . ?
C2 C3 C4 C5 0.8(4) . . . . ?
C2 C3 C4 C13 -178.5(2) . . . . ?
C3 C4 C5 C6 -0.6(4) . . . . ?
C13 C4 C5 C6 178.7(2) . . . . ?
C2 C1 C6 C5 1.0(4) . . . . ?
Br1 C1 C6 C5 -179.93(18) . . . . ?
C4 C5 C6 C1 -0.3(4) . . . . ?
C13 N1 C7 C8 -35.3(3) . . . . ?
C13 N1 C7 C12 146.7(2) . . . . ?
C12 C7 C8 C9 2.7(4) . . . . ?
N1 C7 C8 C9 -175.3(2) . . . . ?
C7 C8 C9 C10 -0.8(4) . . . . ?
C8 C9 C10 C11 -1.0(4) . . . . ?
C8 C9 C10 Cl1 179.1(2) . . . . ?
C9 C10 C11 C12 0.9(4) . . . . ?
Cl1 C10 C11 C12 -179.2(2) . . . . ?
C10 C11 C12 C7 1.1(4) . . . . ?
C8 C7 C12 C11 -2.8(4) . . . . ?
N1 C7 C12 C11 175.2(2) . . . . ?
C7 N1 C13 C4 -64.3(3) . . . . ?
C7 N1 C13 C14 170.65(19) . . . . ?
C5 C4 C13 N1 137.9(2) . . . . ?
C3 C4 C13 N1 -42.8(3) . . . . ?
C5 C4 C13 C14 -99.4(2) . . . . ?
C3 C4 C13 C14 79.8(3) . . . . ?
N1 C13 C14 O1 62.0(3) . . . . ?
C4 C13 C14 O1 -64.6(3) . . . . ?
N1 C13 C14 C15 -58.9(2) . . . . ?
C4 C13 C14 C15 174.43(19) . . . . ?
O1 C14 C15 O2 -2.8(3) . . . . ?
C13 C14 C15 O2 118.9(3) . . . . ?
O1 C14 C15 O3 176.4(2) . . . . ?
C13 C14 C15 O3 -61.9(3) . . . . ?
O2 C15 O3 C16 -6.9(4) . . . . ?
C14 C15 O3 C16 174.0(3) . . . . ?
C17 C16 O3 C15 -85.4(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.495
_refine_diff_density_min         -0.494
_refine_diff_density_rms         0.052