# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2012


data_global

_journal_coden_Cambridge         182

_publ_requested_journal          'Chemical Communications'

loop_
_publ_author_name
'Zhaoguo Zhang'

_publ_contact_author_name        'Zhaoguo Zhang'
_publ_contact_author_address     
;

;

_publ_contact_author_email       zhaoguo@sjtu.edu.cn
# Attachment '- lwf-4s.cif'

data_(S)-4s
_database_code_depnum_ccdc_archive 'CCDC 888973'
#TrackingRef '- lwf-4s.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H19 N O4'
_chemical_formula_weight         253.29

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   P212121

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

_cell_length_a                   7.7341(4)
_cell_length_b                   8.4900(5)
_cell_length_c                   20.9282(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1374.20(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             544
_exptl_absorpt_coefficient_mu    0.748
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\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_reflns_number            7946
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_sigmaI/netI    0.0282
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         4.22
_diffrn_reflns_theta_max         68.33
_reflns_number_total             2426
_reflns_number_gt                2376
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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^)+(0.0692P)^2^+0.1776P] 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   0.0(2)
_refine_ls_number_reflns         2426
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0406
_refine_ls_wR_factor_ref         0.1150
_refine_ls_wR_factor_gt          0.1142
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_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
O1 O 0.81000(17) 0.33766(19) 0.04806(6) 0.0622(4) Uani 1 1 d . . .
N1 N 1.4461(2) 0.4463(2) 0.36918(8) 0.0636(4) Uani 1 1 d . . .
C1 C 0.6370(3) 0.3352(3) 0.03551(10) 0.0637(5) Uani 1 1 d . . .
H1A H 0.5873 0.3043 -0.0041 0.076 Uiso 1 1 calc R . .
O2 O 1.12416(18) 0.3531(3) 0.10330(7) 0.0928(7) Uani 1 1 d . . .
C2 C 0.5475(2) 0.3820(3) 0.08627(9) 0.0590(5) Uani 1 1 d . . .
H2A H 0.4254 0.3910 0.0894 0.071 Uiso 1 1 calc R . .
O3 O 1.19750(17) 0.26375(13) 0.24763(7) 0.0595(3) Uani 1 1 d . . .
H3A H 1.2911 0.2229 0.2358 0.089 Uiso 1 1 calc R . .
C3 C 0.6692(2) 0.4157(2) 0.13482(8) 0.0493(4) Uani 1 1 d . . .
H3B H 0.6445 0.4517 0.1768 0.059 Uiso 1 1 calc R . .
O4 O 1.5195(2) 0.5831(2) 0.28164(7) 0.0787(5) Uani 1 1 d . . .
C4 C 0.8264(2) 0.3870(2) 0.11005(7) 0.0440(4) Uani 1 1 d . . .
C5 C 1.0020(2) 0.3960(2) 0.13491(8) 0.0496(4) Uani 1 1 d . . .
C6 C 1.0228(2) 0.4622(2) 0.20107(8) 0.0488(4) Uani 1 1 d . . .
H6A H 0.9303 0.4191 0.2287 0.059 Uiso 1 1 calc R . .
H6B H 1.0078 0.5779 0.1993 0.059 Uiso 1 1 calc R . .
C7 C 1.1962(2) 0.42561(18) 0.23096(7) 0.0421(3) Uani 1 1 d . . .
H7A H 1.2907 0.4476 0.1996 0.051 Uiso 1 1 calc R . .
C8 C 1.2234(2) 0.5247(2) 0.29117(8) 0.0542(4) Uani 1 1 d . . .
H8A H 1.1913 0.6353 0.2821 0.065 Uiso 1 1 calc R . .
H8B H 1.1462 0.4855 0.3254 0.065 Uiso 1 1 calc R . .
C9 C 1.4078(2) 0.5192(2) 0.31421(8) 0.0531(4) Uani 1 1 d . . .
C10 C 1.3283(4) 0.3384(3) 0.40329(12) 0.0817(7) Uani 1 1 d . . .
H10A H 1.3953 0.2472 0.4194 0.098 Uiso 1 1 calc R . .
H10B H 1.2407 0.2980 0.3730 0.098 Uiso 1 1 calc R . .
C11 C 1.2396(6) 0.4152(5) 0.45749(14) 0.1218(13) Uani 1 1 d . . .
H11A H 1.1628 0.3392 0.4784 0.183 Uiso 1 1 calc R . .
H11B H 1.1714 0.5045 0.4418 0.183 Uiso 1 1 calc R . .
H11C H 1.3256 0.4529 0.4883 0.183 Uiso 1 1 calc R . .
C12 C 1.6246(3) 0.4558(4) 0.39308(12) 0.0813(7) Uani 1 1 d . . .
H12A H 1.6236 0.4540 0.4404 0.098 Uiso 1 1 calc R . .
H12B H 1.6768 0.5567 0.3793 0.098 Uiso 1 1 calc R . .
C13 C 1.7332(4) 0.3204(5) 0.36851(17) 0.1108(11) Uani 1 1 d . . .
H13A H 1.8514 0.3303 0.3849 0.166 Uiso 1 1 calc R . .
H13B H 1.7351 0.3226 0.3217 0.166 Uiso 1 1 calc R . .
H13C H 1.6833 0.2205 0.3831 0.166 Uiso 1 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 0.0386(6) 0.1027(10) 0.0451(6) -0.0193(6) -0.0008(5) -0.0011(7)
N1 0.0563(9) 0.0821(11) 0.0525(8) 0.0019(8) -0.0080(7) -0.0091(9)
C1 0.0426(9) 0.0917(14) 0.0569(10) -0.0105(9) -0.0124(8) -0.0044(9)
O2 0.0356(7) 0.177(2) 0.0654(8) -0.0485(11) 0.0031(6) 0.0048(9)
C2 0.0333(8) 0.0781(12) 0.0657(11) -0.0024(9) -0.0025(8) 0.0016(8)
O3 0.0528(7) 0.0451(6) 0.0807(9) -0.0008(6) 0.0078(6) 0.0015(5)
C3 0.0373(8) 0.0647(10) 0.0460(8) -0.0016(7) 0.0044(7) 0.0039(8)
O4 0.0713(9) 0.1010(12) 0.0637(8) 0.0025(8) 0.0005(7) -0.0370(9)
C4 0.0373(8) 0.0561(8) 0.0386(7) -0.0029(6) 0.0002(6) -0.0008(7)
C5 0.0334(8) 0.0694(11) 0.0459(8) -0.0105(7) 0.0024(7) 0.0004(8)
C6 0.0400(8) 0.0577(9) 0.0487(8) -0.0111(7) -0.0027(7) 0.0052(7)
C7 0.0367(7) 0.0445(7) 0.0451(7) -0.0032(6) 0.0004(6) -0.0020(7)
C8 0.0536(10) 0.0572(10) 0.0517(9) -0.0088(8) -0.0065(8) 0.0019(8)
C9 0.0528(10) 0.0590(10) 0.0477(9) -0.0087(8) -0.0034(7) -0.0132(8)
C10 0.0946(18) 0.0804(15) 0.0701(13) 0.0044(11) -0.0059(13) -0.0065(14)
C11 0.132(3) 0.152(3) 0.0822(18) -0.011(2) 0.0239(19) -0.023(3)
C12 0.0654(13) 0.1070(19) 0.0715(13) -0.0061(13) -0.0201(11) -0.0032(13)
C13 0.0810(19) 0.145(3) 0.106(2) -0.015(2) -0.0144(17) 0.0228(19)

_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 1.364(2) . ?
O1 C4 1.3693(19) . ?
N1 C9 1.340(2) . ?
N1 C12 1.471(3) . ?
N1 C10 1.476(3) . ?
C1 C2 1.329(3) . ?
C1 H1A 0.9500 . ?
O2 C5 1.210(2) . ?
C2 C3 1.414(3) . ?
C2 H2A 0.9500 . ?
O3 C7 1.418(2) . ?
O3 H3A 0.8400 . ?
C3 C4 1.344(2) . ?
C3 H3B 0.9500 . ?
O4 C9 1.227(2) . ?
C4 C5 1.456(2) . ?
C5 C6 1.503(2) . ?
C6 C7 1.512(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.530(2) . ?
C7 H7A 1.0000 . ?
C8 C9 1.506(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C10 C11 1.478(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.514(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?

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 O1 C4 106.15(14) . . ?
C9 N1 C12 118.31(18) . . ?
C9 N1 C10 124.46(17) . . ?
C12 N1 C10 116.7(2) . . ?
C2 C1 O1 110.64(17) . . ?
C2 C1 H1A 124.7 . . ?
O1 C1 H1A 124.7 . . ?
C1 C2 C3 106.77(16) . . ?
C1 C2 H2A 126.6 . . ?
C3 C2 H2A 126.6 . . ?
C7 O3 H3A 109.5 . . ?
C4 C3 C2 106.75(15) . . ?
C4 C3 H3B 126.6 . . ?
C2 C3 H3B 126.6 . . ?
C3 C4 O1 109.68(14) . . ?
C3 C4 C5 134.14(14) . . ?
O1 C4 C5 116.18(14) . . ?
O2 C5 C4 121.14(15) . . ?
O2 C5 C6 122.20(15) . . ?
C4 C5 C6 116.65(13) . . ?
C5 C6 C7 113.53(13) . . ?
C5 C6 H6A 108.9 . . ?
C7 C6 H6A 108.9 . . ?
C5 C6 H6B 108.9 . . ?
C7 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?
O3 C7 C6 107.87(13) . . ?
O3 C7 C8 109.23(14) . . ?
C6 C7 C8 110.47(13) . . ?
O3 C7 H7A 109.7 . . ?
C6 C7 H7A 109.7 . . ?
C8 C7 H7A 109.7 . . ?
C9 C8 C7 112.14(14) . . ?
C9 C8 H8A 109.2 . . ?
C7 C8 H8A 109.2 . . ?
C9 C8 H8B 109.2 . . ?
C7 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
O4 C9 N1 121.69(18) . . ?
O4 C9 C8 118.39(17) . . ?
N1 C9 C8 119.91(16) . . ?
N1 C10 C11 112.6(3) . . ?
N1 C10 H10A 109.1 . . ?
C11 C10 H10A 109.1 . . ?
N1 C10 H10B 109.1 . . ?
C11 C10 H10B 109.1 . . ?
H10A C10 H10B 107.8 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N1 C12 C13 111.3(2) . . ?
N1 C12 H12A 109.4 . . ?
C13 C12 H12A 109.4 . . ?
N1 C12 H12B 109.4 . . ?
C13 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        67.00
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.039