# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is (c) The Royal Society of Chemistry 2007

data_global

_journal_coden_Cambridge         177

loop_
_publ_author_name
'Gunter Helmchen'
'Carola Berthold'
'Stephanie Spiess'
'Robert Weihofen'

_publ_contact_author_name        'Gunter Helmchen'
_publ_contact_author_address     
;
Organisch-Chemisches Institut
Ruprecht-Karls-Universitaet Heidelberg
Im Neuenheimer Feld 270
Heidelberg
69120
GERMANY
;

_publ_contact_author_email       G.HELMCHEN@OCI.UNI-HEIDELBERG.DE

_publ_requested_journal          'Organic & Biomolecular Chemistry'

_publ_section_title              
;
Synthesis of a,b-unsaturated g-lactams via asymmetric
iridium-catalysed allylic substitution
;

data_ssp2
_database_code_depnum_ccdc_archive 'CCDC 644739'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H15 Cl2 N O2'
_chemical_formula_weight         264.14

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)

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

_cell_length_a                   7.3431(3)
_cell_length_b                   6.1580(3)
_cell_length_c                   14.2504(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.8280(10)
_cell_angle_gamma                90.00
_cell_volume                     644.32(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       polyhedron
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             276
_exptl_absorpt_coefficient_mu    0.489
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8359
_exptl_absorpt_correction_T_max  0.9712
_exptl_absorpt_process_details   'Blessing, Acta Cryst. (1995) A51 33-38.'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      200(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            6344
_diffrn_reflns_av_R_equivalents  0.0539
_diffrn_reflns_av_sigmaI/netI    0.0757
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.43
_diffrn_reflns_theta_max         27.40
_reflns_number_total             2881
_reflns_number_gt                2286
_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^)+(0.0303P)^2^+0.0631P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.08(7)
_refine_ls_number_reflns         2881
_refine_ls_number_parameters     170
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0456
_refine_ls_wR_factor_ref         0.0957
_refine_ls_wR_factor_gt          0.0870
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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
Cl1 Cl 0.15874(12) -0.11575(17) 0.60766(6) 0.0566(3) Uani 1 1 d . . .
C1 C 0.6794(4) -0.1322(6) 0.2614(2) 0.0369(8) Uani 1 1 d . . .
H1A H 0.8098 -0.1240 0.2483 0.055 Uiso 1 1 calc R . .
H1B H 0.6623 -0.1540 0.3288 0.055 Uiso 1 1 calc R . .
H1C H 0.6201 0.0034 0.2419 0.055 Uiso 1 1 calc R . .
C2 C 0.5952(3) -0.3217(6) 0.20741(18) 0.0228(6) Uani 1 1 d . . .
H2 H 0.648(4) -0.458(5) 0.236(2) 0.032(9) Uiso 1 1 d . . .
N2 N 0.6544(3) -0.3022(5) 0.10701(15) 0.0248(5) Uani 1 1 d . . .
H2A H 0.590(5) -0.387(6) 0.063(2) 0.046(10) Uiso 1 1 d . . .
H2B H 0.652(5) -0.163(8) 0.080(3) 0.059(12) Uiso 1 1 d . . .
H2C H 0.785(4) -0.335(5) 0.1056(19) 0.032(8) Uiso 1 1 d . . .
C3 C 0.3841(3) -0.3364(5) 0.21121(19) 0.0232(6) Uani 1 1 d . . .
H3 H 0.334(4) -0.227(5) 0.171(2) 0.028(8) Uiso 1 1 d . . .
C4 C 0.3194(4) -0.5589(5) 0.1756(2) 0.0272(6) Uani 1 1 d . . .
H4A H 0.3949 -0.6014 0.1216 0.033 Uiso 1 1 calc R . .
H4B H 0.3403 -0.6674 0.2259 0.033 Uiso 1 1 calc R . .
C5 C 0.1227(4) -0.5673(5) 0.1459(2) 0.0295(7) Uani 1 1 d . . .
O5 O 0.0831(4) -0.7570(4) 0.1059(2) 0.0576(8) Uani 1 1 d . . .
H5 H -0.034(6) -0.750(7) 0.093(3) 0.078(15) Uiso 1 1 d . . .
O6 O 0.0139(3) -0.4228(4) 0.15593(16) 0.0387(6) Uani 1 1 d . . .
C11 C 0.3191(3) -0.2892(5) 0.31044(19) 0.0256(6) Uani 1 1 d . . .
C12 C 0.3644(4) -0.4246(6) 0.3857(2) 0.0366(8) Uani 1 1 d . . .
H12 H 0.4303 -0.5546 0.3745 0.044 Uiso 1 1 calc R . .
C13 C 0.3146(4) -0.3727(6) 0.4766(2) 0.0425(9) Uani 1 1 d . . .
H13 H 0.3460 -0.4666 0.5272 0.051 Uiso 1 1 calc R . .
C14 C 0.2200(4) -0.1851(6) 0.4927(2) 0.0389(9) Uani 1 1 d . . .
C15 C 0.1706(4) -0.0484(6) 0.4197(2) 0.0413(8) Uani 1 1 d . . .
H15 H 0.1034 0.0804 0.4314 0.050 Uiso 1 1 calc R . .
C16 C 0.2205(4) -0.1020(5) 0.3296(2) 0.0330(7) Uani 1 1 d . . .
H16 H 0.1865 -0.0085 0.2793 0.040 Uiso 1 1 calc R . .
Cl2 Cl -0.31525(8) 0.19222(11) 0.04393(5) 0.02902(18) 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
Cl1 0.0479(5) 0.0851(8) 0.0369(5) -0.0231(5) 0.0079(4) -0.0177(5)
C1 0.0315(17) 0.046(2) 0.0327(18) -0.0072(16) -0.0040(13) -0.0074(15)
C2 0.0197(12) 0.0268(15) 0.0218(14) 0.0011(15) -0.0016(10) 0.0005(14)
N2 0.0214(11) 0.0264(12) 0.0264(13) -0.0003(15) -0.0020(9) -0.0015(14)
C3 0.0189(12) 0.0246(18) 0.0261(15) 0.0061(13) -0.0007(10) 0.0011(12)
C4 0.0236(14) 0.0252(15) 0.0328(17) 0.0006(12) 0.0007(12) 0.0011(12)
C5 0.0236(15) 0.0309(17) 0.0341(18) -0.0013(14) -0.0004(12) -0.0052(13)
O5 0.0313(13) 0.0369(17) 0.104(2) -0.0195(13) -0.0200(14) 0.0000(11)
O6 0.0227(11) 0.0406(13) 0.0526(15) -0.0101(11) -0.0052(9) 0.0042(10)
C11 0.0195(12) 0.0272(15) 0.0300(15) 0.0030(15) -0.0021(11) -0.0031(13)
C12 0.0367(18) 0.0389(19) 0.0344(19) 0.0063(15) 0.0048(14) 0.0087(15)
C13 0.045(2) 0.054(2) 0.0283(18) 0.0085(15) 0.0004(15) 0.0075(16)
C14 0.0280(17) 0.060(2) 0.0288(18) -0.0123(17) 0.0053(14) -0.0095(16)
C15 0.0366(18) 0.041(2) 0.046(2) -0.0109(17) 0.0019(16) 0.0031(15)
C16 0.0338(16) 0.0265(17) 0.0385(18) 0.0013(15) -0.0014(13) 0.0022(13)
Cl2 0.0277(3) 0.0240(3) 0.0353(4) -0.0017(4) -0.0064(3) -0.0012(4)

_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
Cl1 C14 1.757(3) . ?
C1 C2 1.524(4) . ?
C2 N2 1.506(3) . ?
C2 C3 1.555(3) . ?
C3 C11 1.527(4) . ?
C3 C4 1.534(4) . ?
C4 C5 1.500(4) . ?
C5 O6 1.206(4) . ?
C5 O5 1.330(4) . ?
C11 C16 1.391(4) . ?
C11 C12 1.395(4) . ?
C12 C13 1.389(4) . ?
C13 C14 1.369(5) . ?
C14 C15 1.383(5) . ?
C15 C16 1.381(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
N2 C2 C1 107.4(3) . . ?
N2 C2 C3 109.8(2) . . ?
C1 C2 C3 115.1(2) . . ?
C11 C3 C4 112.2(2) . . ?
C11 C3 C2 110.2(2) . . ?
C4 C3 C2 110.2(2) . . ?
C5 C4 C3 114.6(2) . . ?
O6 C5 O5 123.9(3) . . ?
O6 C5 C4 125.3(3) . . ?
O5 C5 C4 110.8(3) . . ?
C16 C11 C12 117.7(3) . . ?
C16 C11 C3 120.7(3) . . ?
C12 C11 C3 121.6(3) . . ?
C13 C12 C11 121.1(3) . . ?
C14 C13 C12 119.4(3) . . ?
C13 C14 C15 121.0(3) . . ?
C13 C14 Cl1 119.9(3) . . ?
C15 C14 Cl1 119.1(3) . . ?
C16 C15 C14 119.0(3) . . ?
C15 C16 C11 121.8(3) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.40
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.053

#======================================================================

#_eof # End of Crystallographic Information File