# Supplementary Material (ESI) for Perkin Transactions
# This journal is © The Royal Society of Chemistry 2000
# CCDC Number: 207/459

data_global

_audit_creation_method            SHELXL-97

# SUBMISSION DETAILS

_publ_contact_author
;
 Professor Tim C. Gallagher
 School of Chemistry
 University of Bristol
 Bristol
 BS8 1TS
 UK
;
_publ_contact_author_email        t.gallagher@bris.ac.uk
_publ_contact_author_fax          '+44(0)117 929 8611'
_publ_contact_author_phone        '+44(0)117 928 8260'
_publ_contact_letter
;
 Please consider this CIF submission for publication in
 J Chem Soc Perkin 1
;
_publ_requested_journal           'J Chem Soc Perkin 1'

# TITLE AND AUTHOR LIST

_publ_section_title
;
 Asymmetric Reduction of Prochiral Cycloalkenones.
 The Influence of Exocyclic Alkene Geometry.
;
loop_
_publ_author_name
_publ_author_address
 'Alison F. Simpson'
;
 School of Chemistry
 University of Bristol
 Bristol
 BS8 1TS
 UK
;
 'Corinna Prengel'
;
 School of Chemistry
 University of Bristol
 Bristol
 BS8 1TS
 UK
;
 'Craig P. Butts'
;
 School of Chemistry
 University of Bristol
 Bristol
 BS8 1TS
 UK
;
 'Mark Armitage'
;
 School of Chemistry
 University of Bristol
 Bristol
 BS8 1TS
 UK
;
 'Timothy Gallagher'
;
 School of Chemistry
 University of Bristol
 Bristol
 BS8 1TS
 UK
;

########################################################################
#




data_structure1

_audit_creation_method            SHELXL
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_formula_moiety          ?
_chemical_formula_structural      ?
_chemical_formula_analytical      ?
_chemical_formula_sum             'C21 H23 N O2'
_chemical_formula_weight          321.40
_chemical_melting_point           ?
_chemical_compound_source         ?

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            Orthorhombic
_symmetry_space_group_name_H-M    P2(1)2(1)2(1)

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

_cell_length_a                    5.1199(13)
_cell_length_b                    13.998(4)
_cell_length_c                    24.286(6)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      1740.6(8)
_cell_formula_units_Z             4
_cell_measurement_temperature     173(2)
_cell_measurement_reflns_used     140
_cell_measurement_theta_min       1.75
_cell_measurement_theta_max       27.5

_exptl_crystal_description        Needles
_exptl_crystal_colour             Colourless
_exptl_crystal_size_max           .6
_exptl_crystal_size_mid           .12
_exptl_crystal_size_min           .1
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.226
_exptl_crystal_density_method     None
_exptl_crystal_F_000              688
_exptl_absorpt_coefficient_mu     0.078
_exptl_absorpt_correction_type    none
_exptl_absorpt_correction_T_min   ?
_exptl_absorpt_correction_T_max   ?

_exptl_special_details
;
 ?
;

_diffrn_ambient_temperature       173(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        'Siemens SMART Area Detector'
_diffrn_measurement_method        '\w rotation with narrow frames'
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             18250
_diffrn_reflns_av_R_equivalents   0.0765
_diffrn_reflns_av_sigmaI/netI     0.0745
_diffrn_reflns_limit_h_min        -6
_diffrn_reflns_limit_h_max        6
_diffrn_reflns_limit_k_min        -18
_diffrn_reflns_limit_k_max        17
_diffrn_reflns_limit_l_min        -31
_diffrn_reflns_limit_l_max        31
_diffrn_reflns_theta_min          1.68
_diffrn_reflns_theta_max          27.50
_reflns_number_total              3980
_reflns_number_observed           2526
_reflns_observed_criterion        >2sigma(I)

_computing_data_collection        'SMART (Siemens, 1995b)'
_computing_cell_refinement        'SMART (Siemens, 1995b)'
_computing_data_reduction         'SMART (Siemens, 1995b)'
_computing_structure_solution     'SHELXTL (Siemens, 1995a)'
_computing_structure_refinement   'SHELXTL (Siemens, 1995a)'
_computing_molecular_graphics     'SHELXTL (Siemens, 1995a)'
_computing_publication_material   'SHELXTL (Siemens, 1995a)'

_refine_special_details
;
 Refinement on F^2^ for ALL reflections except for 0 with very negative
F^2^
 or flagged by the user for potential systematic errors.  Weighted
R-factors
 wR and all goodnesses 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 observed
criterion
 of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0476P)^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     noref
_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    -0.27(143)
_refine_ls_number_reflns          3980
_refine_ls_number_parameters      217
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1002
_refine_ls_R_factor_obs           0.0500
_refine_ls_wR_factor_all          0.1033
_refine_ls_wR_factor_obs          0.0878
_refine_ls_goodness_of_fit_all    0.969
_refine_ls_goodness_of_fit_obs    1.049
_refine_ls_restrained_S_all       0.969
_refine_ls_restrained_S_obs       1.049
_refine_ls_shift/esd_max          0.001
_refine_ls_shift/esd_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_thermal_displace_type
 _atom_site_occupancy
 _atom_site_calc_flag
 _atom_site_refinement_flags
 _atom_site_disorder_group
C1 C 0.6340(5) 0.55588(14) -0.00456(8) 0.0320(5) Uani 1 d . .
H1A H 0.8183(5) 0.54213(14) 0.00655(8) 0.038 Uiso 1 calc R .
C2 C 0.5169(4) 0.4790(2) -0.04122(8) 0.0293(5) Uani 1 d . .
C3 C 0.3205(5) 0.5270(2) -0.07901(8) 0.0325(5) Uani 1 d . .
H3A H 0.1422(5) 0.5025(2) -0.07198(8) 0.039 Uiso 1 calc R .
H3B H 0.3653(5) 0.5153(2) -0.11808(8) 0.039 Uiso 1 calc R .
C4 C 0.3370(4) 0.6341(2) -0.06556(9) 0.0355(5) Uani 1 d . .
H4A H 0.3226(4) 0.6731(2) -0.09944(9) 0.043 Uiso 1 calc R .
H4B H 0.1966(4) 0.6531(2) -0.03974(9) 0.043 Uiso 1 calc R .
C5 C 0.6069(5) 0.6461(2) -0.03891(9) 0.0366(5) Uani 1 d . .
H5A H 0.7460(5) 0.6501(2) -0.06714(9) 0.044 Uiso 1 calc R .
H5B H 0.6134(5) 0.7040(2) -0.01549(9) 0.044 Uiso 1 calc R .
C6 C 0.5969(4) 0.38853(15) -0.03945(8) 0.0330(5) Uani 1 d . .
H6A H 0.7317(4) 0.37621(15) -0.01353(8) 0.040 Uiso 1 calc R .
C7 C 0.5107(4) 0.30436(15) -0.07105(8) 0.0315(5) Uani 1 d . .
C8 C 0.6390(5) 0.2177(2) -0.06181(9) 0.0398(6) Uani 1 d . .
H8A H 0.7813(5) 0.2157(2) -0.03673(9) 0.048 Uiso 1 calc R .
C9 C 0.5640(5) 0.1348(2) -0.08824(9) 0.0447(6) Uani 1 d . .
H9A H 0.6533(5) 0.0767(2) -0.08073(9) 0.054 Uiso 1 calc R .
C10 C 0.3623(5) 0.1354(2) -0.12513(9) 0.0432(6) Uani 1 d . .
H10A H 0.3117(5) 0.0784(2) -0.14341(9) 0.052 Uiso 1 calc R .
C11 C 0.2331(5) 0.2200(2) -0.13548(10) 0.0458(7) Uani 1 d . .
H11A H 0.0928(5) 0.2210(2) -0.16107(10) 0.055 Uiso 1 calc R .
C12 C 0.3058(5) 0.3037(2) -0.10892(9) 0.0435(6) Uani 1 d . .
H12A H 0.2147(5) 0.3613(2) -0.11662(9) 0.052 Uiso 1 calc R .
O13 O 0.4551(3) 0.56416(10) 0.04248(5) 0.0350(4) Uani 1 d . .
C14 C 0.5518(5) 0.60585(15) 0.08865(8) 0.0297(5) Uani 1 d . .
O15 O 0.7823(3) 0.61879(11) 0.09761(6) 0.0358(4) Uani 1 d . .
N16 N 0.3561(4) 0.62982(13) 0.12237(6) 0.0323(4) Uani 1 d . .
H16A H 0.1943(4) 0.62228(13) 0.11091(6) 0.039 Uiso 1 calc R .
C17 C 0.4005(4) 0.66794(14) 0.17739(8) 0.0288(5) Uani 1 d . .
H17A H 0.5535(4) 0.71229(14) 0.17579(8) 0.035 Uiso 1 calc R .
C18 C 0.1605(5) 0.7253(2) 0.19489(8) 0.0369(6) Uani 1 d . .
H18A H 0.1245(5) 0.7748(2) 0.16739(8) 0.055 Uiso 1 calc R .
H18B H 0.1935(5) 0.7553(2) 0.23067(8) 0.055 Uiso 1 calc R .
H18C H 0.0096(5) 0.6825(2) 0.19784(8) 0.055 Uiso 1 calc R .
C19 C 0.4584(4) 0.5908(2) 0.21980(8) 0.0318(5) Uani 1 d . .
C20 C 0.3491(6) 0.5008(2) 0.21616(10) 0.0531(7) Uani 1 d . .
H20A H 0.2437(6) 0.4846(2) 0.18534(10) 0.064 Uiso 1 calc R .
C21 C 0.3927(8) 0.4337(2) 0.25748(12) 0.0743(10) Uani 1 d . .
H21A H 0.3183(8) 0.3717(2) 0.25455(12) 0.089 Uiso 1 calc R .
C22 C 0.5412(7) 0.4564(2) 0.30199(12) 0.0722(11) Uani 1 d . .
H22A H 0.5688(7) 0.4103(2) 0.33012(12) 0.087 Uiso 1 calc R .
C23 C 0.6512(6) 0.5451(2) 0.30655(10) 0.0588(8) Uani 1 d . .
H23A H 0.7551(6) 0.5606(2) 0.33770(10) 0.071 Uiso 1 calc R .
C24 C 0.6105(5) 0.6120(2) 0.26563(8) 0.0421(6) Uani 1 d . .
H24A H 0.6876(5) 0.6735(2) 0.26886(8) 0.050 Uiso 1 calc R .

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 0.0275(13) 0.0375(13) 0.0310(11) -0.0084(10) 0.0039(10) -0.0042(11)
C2 0.0266(12) 0.0365(13) 0.0249(10) -0.0019(10) 0.0024(9) -0.0037(11)
C3 0.0268(13) 0.0367(12) 0.0340(11) -0.0057(10) 0.0012(10) 0.0008(11)
C4 0.0335(13) 0.0322(12) 0.0409(12) 0.0005(10) 0.0021(11) 0.0011(12)
C5 0.0352(14) 0.0362(12) 0.0384(12) -0.0033(10) 0.0026(11) -0.0047(11)
C6 0.0319(13) 0.0368(13) 0.0304(11) -0.0015(10) -0.0028(10) 0.0028(11)
C7 0.0326(13) 0.0318(12) 0.0299(11) 0.0002(9) 0.0054(10) 0.0025(10)
C8 0.0438(14) 0.0394(14) 0.0362(12) 0.0010(11) -0.0026(12) 0.0083(13)
C9 0.054(2) 0.0326(13) 0.0481(14) -0.0032(12) 0.0028(12) 0.0109(13)
C10 0.050(2) 0.0329(13) 0.0464(13) -0.0079(11) 0.0059(13) -0.0019(13)
C11 0.045(2) 0.043(2) 0.0498(15) -0.0093(12) -0.0102(12) 0.0003(13)
C12 0.044(2) 0.0343(14) 0.0524(14) -0.0038(11) -0.0132(12) 0.0062(12)
O13 0.0296(9) 0.0472(9) 0.0282(8) -0.0087(7) 0.0037(7) -0.0087(7)
C14 0.0306(13) 0.0302(12) 0.0281(11) 0.0006(9) -0.0008(10) -0.0053(11)
O15 0.0244(9) 0.0442(10) 0.0389(8) -0.0075(7) -0.0021(7) -0.0018(8)
N16 0.0198(9) 0.0500(11) 0.0270(9) -0.0076(8) -0.0013(8) -0.0041(10)
C17 0.0260(13) 0.0318(12) 0.0285(10) -0.0041(9) -0.0013(9) -0.0022(10)
C18 0.0336(14) 0.0420(13) 0.0351(12) -0.0060(10) -0.0033(11) 0.0048(12)
C19 0.0292(13) 0.0370(13) 0.0291(11) -0.0035(10) 0.0075(10) 0.0032(11)
C20 0.073(2) 0.044(2) 0.0424(14) -0.0032(12) 0.0058(15) -0.007(2)
C21 0.126(3) 0.0371(15) 0.060(2) 0.0031(14) 0.029(2) 0.004(2)
C22 0.107(3) 0.063(2) 0.047(2) 0.0144(15) 0.025(2) 0.042(2)
C23 0.063(2) 0.081(2) 0.0333(13) 0.0082(14) 0.0019(14) 0.025(2)
C24 0.0362(14) 0.058(2) 0.0324(12) -0.0012(12) 0.0035(11) 0.0092(13)

_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 O13 1.469(2) . ?
C1 C2 1.520(3) . ?
C1 C5 1.520(3) . ?
C2 C6 1.332(3) . ?
C2 C3 1.518(3) . ?
C3 C4 1.537(3) . ?
C4 C5 1.536(3) . ?
C6 C7 1.474(3) . ?
C7 C12 1.395(3) . ?
C7 C8 1.398(3) . ?
C8 C9 1.380(3) . ?
C9 C10 1.367(3) . ?
C10 C11 1.380(3) . ?
C11 C12 1.387(3) . ?
O13 C14 1.358(2) . ?
C14 O15 1.214(2) . ?
C14 N16 1.337(3) . ?
N16 C17 1.457(2) . ?
C17 C19 1.521(3) . ?
C17 C18 1.528(3) . ?
C19 C20 1.382(3) . ?
C19 C24 1.390(3) . ?
C20 C21 1.393(3) . ?
C21 C22 1.359(4) . ?
C22 C23 1.368(4) . ?
C23 C24 1.382(3) . ?

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
O13 C1 C2 105.4(2) . . ?
O13 C1 C5 107.7(2) . . ?
C2 C1 C5 103.4(2) . . ?
C6 C2 C3 130.1(2) . . ?
C6 C2 C1 122.2(2) . . ?
C3 C2 C1 107.6(2) . . ?
C2 C3 C4 105.5(2) . . ?
C5 C4 C3 104.2(2) . . ?
C1 C5 C4 102.9(2) . . ?
C2 C6 C7 130.6(2) . . ?
C12 C7 C8 116.9(2) . . ?
C12 C7 C6 125.0(2) . . ?
C8 C7 C6 118.0(2) . . ?
C9 C8 C7 121.6(2) . . ?
C10 C9 C8 120.6(2) . . ?
C9 C10 C11 119.2(2) . . ?
C10 C11 C12 120.7(2) . . ?
C11 C12 C7 120.9(2) . . ?
C14 O13 C1 116.7(2) . . ?
O15 C14 N16 125.6(2) . . ?
O15 C14 O13 124.5(2) . . ?
N16 C14 O13 109.9(2) . . ?
C14 N16 C17 122.5(2) . . ?
N16 C17 C19 113.1(2) . . ?
N16 C17 C18 108.8(2) . . ?
C19 C17 C18 109.9(2) . . ?
C20 C19 C24 118.2(2) . . ?
C20 C19 C17 121.7(2) . . ?
C24 C19 C17 120.0(2) . . ?
C19 C20 C21 120.3(3) . . ?
C22 C21 C20 120.3(3) . . ?
C21 C22 C23 120.5(3) . . ?
C22 C23 C24 119.7(3) . . ?
C23 C24 C19 121.0(2) . . ?

_refine_diff_density_max    0.151
_refine_diff_density_min   -0.190
_refine_diff_density_rms    0.040

#===END