Supplementary Material (ESI) for Chemical Communications
This journal is (C) The Royal Society of Chemistry 2001

data_Compound_2

_database_code_CSD	169247

_journal_coden_Cambridge      182

_publ_requested_journal       'Chemical Communications'

loop_
_publ_author_name
'Donohoe, Timothy'
'Helliwell, Madeleine'
'Johnson, Peter D.'
'Keenan, Martine'

_publ_contact_author_name     	'Dr Timothy Donohoe'  
_publ_contact_author_address 
;
Dr Timothy Donohoe
Chemistry
University of Manchester
Department of Chemistry
Oxford Road
Manchester
M13 9PL
UNITED KINGDOM
;

_publ_contact_author_email       'T.J.DONOHOE@MAN.AC.UK'

_publ_section_title
;The Regioselective Aminohydroxylation of Allylic Carbamates
;
_audit_creation_date '19101-03-07'
_audit_creation_method 'by teXsan v1.7'
_audit_update_record
;
The data were collected using the RAXIS in 103 x 3 degree
phi oscillations of 10 minutes per exposure. The structure was
solved by direct methods. H atoms bonded to C were included
in calculated positions, and those bonded to N and O were
found by difference Fourier methods and refined isotropically.
The non-H atoms were refined anisotropically.
Molecular Structure Corporation. (1995). teXsan.
Single Crystal Structure Analysis Software. Version 1.7.
MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA.
Altomare, A., Cascarano, M.,
Giacovazzo, C., Guagliardi, A. (1993).
J. Appl. Cryst., 26, 343.
;
_chemical_name_common ?
_chemical_formula_moiety ?
_chemical_formula_sum
'C10 H11 N O3'
_chemical_formula_weight 193.20
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'
'O' 'O' 0.0106 0.0060
'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'
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M 'P 21/n '
_symmetry_Int_Tables_number 14
_symmetry_space_group_name_Hall ?
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 7.551(4)
_cell_length_b 23.367(3)
_cell_length_c 5.612(5)
_cell_angle_alpha 90.00
_cell_angle_beta 111.25(6)
_cell_angle_gamma 90.00
_cell_volume 922.7(9)
_cell_formula_units_Z 4
_cell_measurement_temperature 293(2)
_cell_measurement_reflns_used 21
_cell_measurement_theta_min 7.2
_cell_measurement_theta_max 9.2
_exptl_crystal_description 'plate'
_exptl_crystal_colour 'colourless'
_exptl_crystal_size_max 0.45
_exptl_crystal_size_mid 0.38
_exptl_crystal_size_min 0.08
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.391
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 408
_exptl_absorpt_coefficient_mu 0.104
_exptl_absorpt_correction_type none
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_T_max ?
_exptl_special_details ?
_diffrn_ambient_temperature 293(2)
_diffrn_radiation_wavelength 0.71069
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'Rigaku rotating anode'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_detector 'image plate'
_diffrn_measurement_device 'Rigaku RAXIS'
_diffrn_measurement_method '103 x 3 degree phi scans'
_diffrn_standards_number 0
_diffrn_standards_interval_count 0
_diffrn_standards_decay_% 0.00
_diffrn_reflns_number 11748
_diffrn_reflns_av_R_equivalents 0.047
_diffrn_reflns_av_sigmaI/netI 0.0371
_diffrn_reflns_limit_h_min -8
_diffrn_reflns_limit_h_max 8
_diffrn_reflns_limit_k_min -27
_diffrn_reflns_limit_k_max 0
_diffrn_reflns_limit_l_min 0
_diffrn_reflns_limit_l_max 6
_diffrn_reflns_theta_min 3.02
_diffrn_reflns_theta_max 25.06
_reflns_number_total 1520
_reflns_number_gt 1303
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'MSC RAXIS11 Control'
_computing_cell_refinement 'DENZO (Otwinowski, Z. 1988)'
_computing_data_reduction 'DENZO (Otwinowski, Z. 1988)'
_computing_structure_solution
;
SHELXS86 (Sheldrick, 1985)
;
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_publication_material 'teXsan (MSC, 1995)'
_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 w=1/[\s^2^(Fo^2^)+(0.0533P)^2^+0.2561P] 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 0.086(15)
_refine_ls_extinction_expression
'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^'
_refine_ls_number_reflns 1520
_refine_ls_number_parameters 136
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0460
_refine_ls_R_factor_gt 0.0390
_refine_ls_wR_factor_ref 0.1121
_refine_ls_wR_factor_gt 0.1067
_refine_ls_goodness_of_fit_ref 1.048
_refine_ls_restrained_S_all 1.048
_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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.37167(15) 0.97717(5) 0.1595(2) 0.0479(4) Uani 1 d . . .
O2 O 0.54269(16) 0.90840(5) 0.0638(2) 0.0490(4) Uani 1 d . . .
O3 O 1.01331(19) 0.94230(6) 0.8281(2) 0.0549(4) Uani 1 d . . .
H3O H 1.127(4) 0.9529(10) 0.901(5) 0.077(8) Uiso 1 d . . .
N1 N 0.6679(2) 0.95085(7) 0.4371(3) 0.0470(4) Uani 1 d . . .
H1N H 0.663(3) 0.9701(9) 0.564(4) 0.056(6) Uiso 1 d . . .
C1 C 0.5179(2) 0.94878(7) 0.2208(3) 0.0394(4) Uani 1 d . . .
C2 C 0.7338(2) 0.88616(8) 0.1772(3) 0.0500(5) Uani 1 d . . .
H2A H 0.8169 0.9036 0.1004 0.060 Uiso 1 calc R . .
H2B H 0.7353 0.8450 0.1565 0.060 Uiso 1 calc R . .
C3 C 0.7948(2) 0.90233(7) 0.4601(3) 0.0445(5) Uani 1 d . . .
H3 H 0.7627 0.8713 0.5548 0.053 Uiso 1 calc R . .
C4 C 1.0016(2) 0.91849(7) 0.5897(3) 0.0442(4) Uani 1 d . . .
H4 H 1.0350 0.9478 0.4881 0.053 Uiso 1 calc R . .
C5 C 1.1309(2) 0.86694(7) 0.6220(3) 0.0393(4) Uani 1 d . . .
C6 C 1.1439(2) 0.82500(8) 0.8021(3) 0.0486(5) Uani 1 d . . .
H6 H 1.0678 0.8273 0.9001 0.058 Uiso 1 calc R . .
C7 C 1.2689(3) 0.77970(8) 0.8376(4) 0.0561(5) Uani 1 d . . .
H7 H 1.2770 0.7520 0.9600 0.067 Uiso 1 calc R . .
C8 C 1.3810(3) 0.77554(8) 0.6928(4) 0.0576(5) Uani 1 d . . .
H8 H 1.4663 0.7454 0.7185 0.069 Uiso 1 calc R . .
C9 C 1.3667(3) 0.81608(9) 0.5101(4) 0.0570(5) Uani 1 d . . .
H9 H 1.4408 0.8130 0.4096 0.068 Uiso 1 calc R . .
C10 C 1.2424(2) 0.86163(8) 0.4746(3) 0.0482(5) Uani 1 d . . .
H10 H 1.2338 0.8889 0.3503 0.058 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
O1 0.0344(7) 0.0548(8) 0.0464(7) -0.0024(5) 0.0048(5) 0.0050(5)
O2 0.0419(7) 0.0522(7) 0.0418(7) -0.0100(5) 0.0020(6) 0.0047(5)
O3 0.0377(8) 0.0653(9) 0.0522(8) -0.0221(6) 0.0051(6) 0.0029(6)
N1 0.0351(8) 0.0572(9) 0.0394(8) -0.0110(7) 0.0022(7) 0.0092(6)
C1 0.0338(9) 0.0421(9) 0.0380(9) -0.0017(6) 0.0079(7) -0.0013(7)
C2 0.0423(10) 0.0530(11) 0.0466(10) -0.0089(8) 0.0062(8) 0.0086(8)
C3 0.0379(9) 0.0445(9) 0.0457(10) -0.0026(7) 0.0086(8) 0.0033(7)
C4 0.0377(9) 0.0445(9) 0.0453(10) -0.0029(7) 0.0089(8) 0.0021(7)
C5 0.0330(9) 0.0414(9) 0.0373(9) -0.0028(6) 0.0053(7) -0.0007(6)
C6 0.0471(10) 0.0537(11) 0.0452(10) 0.0013(7) 0.0170(8) 0.0006(8)
C7 0.0618(12) 0.0443(10) 0.0537(11) 0.0075(8) 0.0108(10) 0.0049(8)
C8 0.0456(10) 0.0490(11) 0.0671(13) -0.0072(9) 0.0070(10) 0.0099(8)
C9 0.0425(10) 0.0659(12) 0.0651(12) -0.0097(10) 0.0226(9) 0.0017(9)
C10 0.0437(10) 0.0528(11) 0.0470(10) 0.0026(7) 0.0150(8) -0.0019(8)
_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
O1 C1 1.226(2) . ?
O2 C1 1.349(2) . ?
O2 C2 1.446(2) . ?
O3 C4 1.422(2) . ?
O3 H3O 0.84(3) . ?
N1 C1 1.327(3) . ?
N1 C3 1.460(2) . ?
N1 H1N 0.85(2) . ?
C2 C3 1.531(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.512(2) . ?
C3 H3 0.9800 . ?
C4 C5 1.520(2) . ?
C4 H4 0.9800 . ?
C5 C10 1.383(3) . ?
C5 C6 1.385(2) . ?
C6 C7 1.384(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.373(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.371(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.385(3) . ?
C9 H9 0.9300 . ?
C10 H10 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 O2 C2 108.43(13) . . ?
C4 O3 H3O 106.0(16) . . ?
C1 N1 C3 111.58(14) . . ?
C1 N1 H1N 120.1(14) . . ?
C3 N1 H1N 124.1(14) . . ?
O1 C1 N1 128.34(16) . . ?
O1 C1 O2 121.26(16) . . ?
N1 C1 O2 110.39(14) . . ?
O2 C2 C3 104.19(14) . . ?
O2 C2 H2A 110.9 . . ?
C3 C2 H2A 110.9 . . ?
O2 C2 H2B 110.9 . . ?
C3 C2 H2B 110.9 . . ?
H2A C2 H2B 108.9 . . ?
N1 C3 C4 112.27(14) . . ?
N1 C3 C2 99.12(14) . . ?
C4 C3 C2 115.52(15) . . ?
N1 C3 H3 109.8 . . ?
C4 C3 H3 109.8 . . ?
C2 C3 H3 109.8 . . ?
O3 C4 C3 104.58(14) . . ?
O3 C4 C5 112.32(14) . . ?
C3 C4 C5 111.49(14) . . ?
O3 C4 H4 109.4 . . ?
C3 C4 H4 109.4 . . ?
C5 C4 H4 109.4 . . ?
C10 C5 C6 118.38(16) . . ?
C10 C5 C4 120.27(15) . . ?
C6 C5 C4 121.34(15) . . ?
C7 C6 C5 120.70(17) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C8 C7 C6 120.23(18) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C9 C8 C7 119.68(18) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C8 C9 C10 120.28(18) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C5 C10 C9 120.71(17) . . ?
C5 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
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
C3 N1 C1 O1 167.75(16) . . . . ?
C3 N1 C1 O2 -11.1(2) . . . . ?
C2 O2 C1 O1 174.81(15) . . . . ?
C2 O2 C1 N1 -6.25(19) . . . . ?
C1 O2 C2 C3 19.70(18) . . . . ?
C1 N1 C3 C4 144.40(16) . . . . ?
C1 N1 C3 C2 21.90(19) . . . . ?
O2 C2 C3 N1 -23.89(17) . . . . ?
O2 C2 C3 C4 -144.02(15) . . . . ?
N1 C3 C4 O3 55.98(18) . . . . ?
C2 C3 C4 O3 168.64(14) . . . . ?
N1 C3 C4 C5 177.60(14) . . . . ?
C2 C3 C4 C5 -69.74(19) . . . . ?
O3 C4 C5 C10 -134.77(17) . . . . ?
C3 C4 C5 C10 108.22(18) . . . . ?
O3 C4 C5 C6 43.7(2) . . . . ?
C3 C4 C5 C6 -73.3(2) . . . . ?
C10 C5 C6 C7 1.6(3) . . . . ?
C4 C5 C6 C7 -176.94(16) . . . . ?
C5 C6 C7 C8 -0.5(3) . . . . ?
C6 C7 C8 C9 -0.9(3) . . . . ?
C7 C8 C9 C10 1.2(3) . . . . ?
C6 C5 C10 C9 -1.3(3) . . . . ?
C4 C5 C10 C9 177.22(16) . . . . ?
C8 C9 C10 C5 -0.1(3) . . . . ?
_diffrn_measured_fraction_theta_max 0.908
_diffrn_reflns_theta_full 25.06
_diffrn_measured_fraction_theta_full 0.908
_refine_diff_density_max 0.293
_refine_diff_density_min -0.160
_refine_diff_density_rms 0.032