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


data_global
_journal_name_full               Chem.Commun.
_journal_coden_cambridge         0182
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_author_name                'Zheng-Hui Guan'
_publ_contact_author_name        'Guan, Zheng-Hui'
_publ_contact_author_email       guanzhh@nwu.edu.cn

data_xb5259
_database_code_depnum_ccdc_archive 'CCDC 876059'
#TrackingRef '- xb5259.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H17 N O5'
_chemical_formula_weight         315.32

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           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   8.158(2)
_cell_length_b                   8.3923(18)
_cell_length_c                   11.774(2)
_cell_angle_alpha                73.710(3)
_cell_angle_beta                 86.066(3)
_cell_angle_gamma                86.367(3)
_cell_volume                     771.1(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    921
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      25.96

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             332
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9639
_exptl_absorpt_correction_T_max  0.9868
_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3921
_diffrn_reflns_av_R_equivalents  0.0191
_diffrn_reflns_av_sigmaI/netI    0.0429
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.80
_diffrn_reflns_theta_max         25.09
_reflns_number_total             2725
_reflns_number_gt                1920
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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^)+(0.1138P)^2^+0.0158P] 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         2725
_refine_ls_number_parameters     212
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0770
_refine_ls_R_factor_gt           0.0533
_refine_ls_wR_factor_ref         0.1920
_refine_ls_wR_factor_gt          0.1624
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_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 0.1760(2) 0.2094(2) 0.04980(16) 0.0394(5) Uani 1 1 d . . .
O1 O 0.4471(3) 0.7160(2) -0.19828(17) 0.0658(6) Uani 1 1 d . . .
O2 O 0.4998(2) 0.5337(2) -0.30174(14) 0.0544(5) Uani 1 1 d . . .
O3 O 0.5756(2) 0.1693(2) -0.20811(14) 0.0532(5) Uani 1 1 d . . .
O4 O 0.3542(2) 0.2214(2) -0.31665(14) 0.0561(5) Uani 1 1 d . . .
O5 O -0.1610(2) 0.1854(2) 0.42751(15) 0.0576(5) Uani 1 1 d . . .
C1 C 0.5825(4) 0.6568(4) -0.3939(2) 0.0626(8) Uani 1 1 d . . .
H1A H 0.5080 0.7504 -0.4231 0.094 Uiso 1 1 calc R . .
H1B H 0.6196 0.6101 -0.4574 0.094 Uiso 1 1 calc R . .
H1C H 0.6753 0.6922 -0.3629 0.094 Uiso 1 1 calc R . .
C2 C 0.4374(3) 0.5806(3) -0.2091(2) 0.0420(6) Uani 1 1 d . . .
C3 C 0.3497(3) 0.4441(3) -0.12043(19) 0.0374(6) Uani 1 1 d . . .
C4 C 0.2700(3) 0.4830(3) -0.02405(19) 0.0384(6) Uani 1 1 d . . .
H4 H 0.2737 0.5897 -0.0157 0.046 Uiso 1 1 calc R . .
C5 C 0.1842(3) 0.3631(3) 0.06068(18) 0.0360(5) Uani 1 1 d . . .
C6 C 0.0971(3) 0.3974(3) 0.16718(19) 0.0364(5) Uani 1 1 d . . .
C7 C 0.1010(3) 0.5490(3) 0.1903(2) 0.0482(6) Uani 1 1 d . . .
H7 H 0.1599 0.6336 0.1388 0.058 Uiso 1 1 calc R . .
C8 C 0.0178(3) 0.5754(3) 0.2898(2) 0.0544(7) Uani 1 1 d . . .
H8 H 0.0206 0.6785 0.3044 0.065 Uiso 1 1 calc R . .
C9 C -0.0684(3) 0.4533(3) 0.3674(2) 0.0491(7) Uani 1 1 d . . .
H9 H -0.1241 0.4726 0.4342 0.059 Uiso 1 1 calc R . .
C10 C -0.0721(3) 0.3005(3) 0.34539(19) 0.0405(6) Uani 1 1 d . . .
C11 C 0.0095(3) 0.2725(3) 0.24544(19) 0.0382(6) Uani 1 1 d . . .
H11 H 0.0055 0.1696 0.2306 0.046 Uiso 1 1 calc R . .
C12 C 0.2528(3) 0.1704(3) -0.04313(19) 0.0412(6) Uani 1 1 d . . .
C13 C 0.3425(3) 0.2840(3) -0.13078(18) 0.0376(6) Uani 1 1 d . . .
C14 C 0.4220(3) 0.2255(3) -0.2312(2) 0.0416(6) Uani 1 1 d . . .
C15 C 0.6611(4) 0.0988(4) -0.2950(3) 0.0715(9) Uani 1 1 d . . .
H15A H 0.5934 0.0202 -0.3126 0.107 Uiso 1 1 calc R . .
H15B H 0.7621 0.0437 -0.2644 0.107 Uiso 1 1 calc R . .
H15C H 0.6848 0.1857 -0.3660 0.107 Uiso 1 1 calc R . .
C16 C 0.2355(4) -0.0044(3) -0.0489(2) 0.0579(7) Uani 1 1 d . . .
H16A H 0.2137 -0.0753 0.0296 0.087 Uiso 1 1 calc R . .
H16B H 0.3355 -0.0428 -0.0825 0.087 Uiso 1 1 calc R . .
H16C H 0.1462 -0.0066 -0.0973 0.087 Uiso 1 1 calc R . .
C17 C -0.1803(4) 0.0312(4) 0.4050(3) 0.0674(9) Uani 1 1 d . . .
H17A H -0.2311 0.0494 0.3310 0.101 Uiso 1 1 calc R . .
H17B H -0.2483 -0.0362 0.4677 0.101 Uiso 1 1 calc R . .
H17C H -0.0744 -0.0246 0.4012 0.101 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
N1 0.0494(12) 0.0364(11) 0.0324(10) -0.0103(8) 0.0055(8) -0.0059(8)
O1 0.0883(15) 0.0485(12) 0.0591(12) -0.0138(9) 0.0182(10) -0.0207(10)
O2 0.0674(12) 0.0508(11) 0.0407(10) -0.0082(8) 0.0191(8) -0.0141(9)
O3 0.0527(12) 0.0600(12) 0.0455(10) -0.0166(8) 0.0072(8) 0.0051(9)
O4 0.0652(12) 0.0709(13) 0.0370(10) -0.0225(9) 0.0003(8) -0.0080(9)
O5 0.0678(13) 0.0631(12) 0.0428(10) -0.0181(8) 0.0218(9) -0.0203(9)
C1 0.0672(19) 0.0663(18) 0.0430(15) 0.0011(13) 0.0184(13) -0.0164(14)
C2 0.0434(14) 0.0426(15) 0.0368(13) -0.0059(11) 0.0003(10) -0.0039(11)
C3 0.0387(13) 0.0410(13) 0.0303(11) -0.0055(10) -0.0028(9) -0.0037(10)
C4 0.0438(14) 0.0364(12) 0.0347(12) -0.0095(10) 0.0005(10) -0.0038(10)
C5 0.0387(13) 0.0380(13) 0.0302(11) -0.0078(9) -0.0011(9) -0.0032(10)
C6 0.0370(12) 0.0417(13) 0.0307(11) -0.0105(10) -0.0015(9) -0.0018(10)
C7 0.0589(16) 0.0405(14) 0.0460(14) -0.0139(11) 0.0068(12) -0.0101(12)
C8 0.0665(18) 0.0453(15) 0.0576(16) -0.0257(13) 0.0082(13) -0.0085(13)
C9 0.0518(16) 0.0600(17) 0.0420(14) -0.0268(12) 0.0068(11) -0.0040(12)
C10 0.0409(13) 0.0469(14) 0.0334(12) -0.0115(10) 0.0032(10) -0.0045(10)
C11 0.0431(14) 0.0361(12) 0.0357(12) -0.0105(10) 0.0002(10) -0.0033(10)
C12 0.0494(14) 0.0415(13) 0.0318(12) -0.0094(10) 0.0032(10) -0.0049(11)
C13 0.0403(13) 0.0430(13) 0.0290(11) -0.0096(10) 0.0005(9) -0.0019(10)
C14 0.0492(15) 0.0385(13) 0.0337(12) -0.0054(10) 0.0066(11) -0.0068(10)
C15 0.068(2) 0.078(2) 0.0689(19) -0.0301(16) 0.0190(15) 0.0125(16)
C16 0.081(2) 0.0476(15) 0.0472(15) -0.0184(12) 0.0165(13) -0.0163(13)
C17 0.086(2) 0.0585(18) 0.0569(17) -0.0159(14) 0.0232(15) -0.0288(16)

_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 C12 1.333(3) . ?
N1 C5 1.337(3) . ?
O1 C2 1.186(3) . ?
O2 C2 1.321(3) . ?
O2 C1 1.435(3) . ?
O3 C14 1.329(3) . ?
O3 C15 1.439(3) . ?
O4 C14 1.191(3) . ?
O5 C10 1.365(3) . ?
O5 C17 1.412(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.498(3) . ?
C3 C4 1.378(3) . ?
C3 C13 1.388(3) . ?
C4 C5 1.389(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.488(3) . ?
C6 C7 1.376(3) . ?
C6 C11 1.386(3) . ?
C7 C8 1.379(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.363(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.380(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.382(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.394(3) . ?
C12 C16 1.503(3) . ?
C13 C14 1.497(3) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

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
C12 N1 C5 119.50(19) . . ?
C2 O2 C1 116.8(2) . . ?
C14 O3 C15 115.5(2) . . ?
C10 O5 C17 117.87(18) . . ?
O2 C1 H1A 109.5 . . ?
O2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 O2 123.9(2) . . ?
O1 C2 C3 123.9(2) . . ?
O2 C2 C3 112.2(2) . . ?
C4 C3 C13 118.9(2) . . ?
C4 C3 C2 117.0(2) . . ?
C13 C3 C2 124.1(2) . . ?
C3 C4 C5 120.0(2) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
N1 C5 C4 121.0(2) . . ?
N1 C5 C6 116.61(19) . . ?
C4 C5 C6 122.4(2) . . ?
C7 C6 C11 119.1(2) . . ?
C7 C6 C5 122.1(2) . . ?
C11 C6 C5 118.8(2) . . ?
C6 C7 C8 120.1(2) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C9 C8 C7 121.3(2) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C8 C9 C10 119.1(2) . . ?
C8 C9 H9 120.5 . . ?
C10 C9 H9 120.5 . . ?
O5 C10 C9 115.3(2) . . ?
O5 C10 C11 124.4(2) . . ?
C9 C10 C11 120.3(2) . . ?
C10 C11 C6 120.1(2) . . ?
C10 C11 H11 119.9 . . ?
C6 C11 H11 119.9 . . ?
N1 C12 C13 122.6(2) . . ?
N1 C12 C16 115.9(2) . . ?
C13 C12 C16 121.5(2) . . ?
C3 C13 C12 118.0(2) . . ?
C3 C13 C14 124.4(2) . . ?
C12 C13 C14 117.5(2) . . ?
O4 C14 O3 124.8(2) . . ?
O4 C14 C13 124.7(2) . . ?
O3 C14 C13 110.42(19) . . ?
O3 C15 H15A 109.5 . . ?
O3 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O3 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C12 C16 H16A 109.5 . . ?
C12 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C12 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O5 C17 H17A 109.5 . . ?
O5 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O5 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

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
C1 O2 C2 O1 -0.5(4) . . . . ?
C1 O2 C2 C3 178.22(19) . . . . ?
O1 C2 C3 C4 3.1(4) . . . . ?
O2 C2 C3 C4 -175.6(2) . . . . ?
O1 C2 C3 C13 -177.8(2) . . . . ?
O2 C2 C3 C13 3.5(3) . . . . ?
C13 C3 C4 C5 -0.1(3) . . . . ?
C2 C3 C4 C5 179.05(19) . . . . ?
C12 N1 C5 C4 0.6(3) . . . . ?
C12 N1 C5 C6 -179.39(19) . . . . ?
C3 C4 C5 N1 -0.6(3) . . . . ?
C3 C4 C5 C6 179.40(19) . . . . ?
N1 C5 C6 C7 177.8(2) . . . . ?
C4 C5 C6 C7 -2.3(4) . . . . ?
N1 C5 C6 C11 -2.2(3) . . . . ?
C4 C5 C6 C11 177.8(2) . . . . ?
C11 C6 C7 C8 -0.3(4) . . . . ?
C5 C6 C7 C8 179.7(2) . . . . ?
C6 C7 C8 C9 0.5(4) . . . . ?
C7 C8 C9 C10 0.0(4) . . . . ?
C17 O5 C10 C9 175.0(2) . . . . ?
C17 O5 C10 C11 -4.4(4) . . . . ?
C8 C9 C10 O5 179.9(2) . . . . ?
C8 C9 C10 C11 -0.6(4) . . . . ?
O5 C10 C11 C6 -179.8(2) . . . . ?
C9 C10 C11 C6 0.7(3) . . . . ?
C7 C6 C11 C10 -0.2(3) . . . . ?
C5 C6 C11 C10 179.7(2) . . . . ?
C5 N1 C12 C13 0.0(3) . . . . ?
C5 N1 C12 C16 -179.3(2) . . . . ?
C4 C3 C13 C12 0.7(3) . . . . ?
C2 C3 C13 C12 -178.3(2) . . . . ?
C4 C3 C13 C14 179.4(2) . . . . ?
C2 C3 C13 C14 0.4(4) . . . . ?
N1 C12 C13 C3 -0.7(3) . . . . ?
C16 C12 C13 C3 178.6(2) . . . . ?
N1 C12 C13 C14 -179.6(2) . . . . ?
C16 C12 C13 C14 -0.2(3) . . . . ?
C15 O3 C14 O4 -0.2(3) . . . . ?
C15 O3 C14 C13 175.9(2) . . . . ?
C3 C13 C14 O4 -95.4(3) . . . . ?
C12 C13 C14 O4 83.3(3) . . . . ?
C3 C13 C14 O3 88.4(3) . . . . ?
C12 C13 C14 O3 -92.8(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        25.09
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.070