# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2011


data_global
#TrackingRef '- 832992.cif'

_journal_name_full               Chem.Commun.
_journal_coden_cambridge         0182
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_name        'Dan-Dan Li'
_publ_contact_author_email       dandanli@mail.ustc.edu.cn
loop_
_publ_author_name
'Dan-Dan Li'
'Ting-Ting Yuan'
'Guan-Wu Wang'

data_110112
#TrackingRef '- 832992.cif'

_database_code_depnum_ccdc_archive 'CCDC 832992'
#TrackingRef '110112.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H11 N O4'
_chemical_formula_weight         233.22

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           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'

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

_cell_length_a                   8.0492(6)
_cell_length_b                   19.9116(11)
_cell_length_c                   7.3009(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.729(8)
_cell_angle_gamma                90.00
_cell_volume                     1114.56(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    291(2)
_cell_measurement_reflns_used    1748
_cell_measurement_theta_min      4.4446
_cell_measurement_theta_max      67.4731

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             488
_exptl_absorpt_coefficient_mu    0.888
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7765
_exptl_absorpt_correction_T_max  0.8424
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      291(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Gemini S Ultra, Oxford Diffraction'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean 15.9149
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3702
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_av_sigmaI/netI    0.0348
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         4.44
_diffrn_reflns_theta_max         67.37
_reflns_number_total             1950
_reflns_number_gt                1623
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro (Oxford Diffraction Ltd.)'
_computing_cell_refinement       'CrysAlisPro (Oxford Diffraction Ltd.)'
_computing_data_reduction        'CrysAlisPro (Oxford Diffraction Ltd.)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-97

_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^)+(0.0402P)^2^+0.0855P] 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    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0101(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         1950
_refine_ls_number_parameters     157
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0380
_refine_ls_wR_factor_ref         0.1052
_refine_ls_wR_factor_gt          0.0931
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_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
O4 O 0.88108(17) 0.38002(6) 1.12977(17) 0.0568(4) Uani 1 1 d . . .
O1 O 0.81703(18) 0.03264(6) 1.09069(19) 0.0658(4) Uani 1 1 d . . .
O2 O 1.03194(16) 0.14604(6) 1.22097(16) 0.0560(4) Uani 1 1 d . . .
O3 O 0.65343(19) 0.34703(6) 0.88309(18) 0.0645(4) Uani 1 1 d . . .
C9 C 0.8560(2) 0.26658(8) 1.0737(2) 0.0465(4) Uani 1 1 d . . .
H9 H 0.9671 0.2657 1.1619 0.056 Uiso 1 1 calc R . .
N1 N 0.86921(18) 0.14669(7) 1.08663(19) 0.0485(4) Uani 1 1 d . . .
C10 C 0.7817(2) 0.33302(9) 1.0145(2) 0.0480(4) Uani 1 1 d . . .
C3 C 0.4707(2) 0.21755(9) 0.7625(2) 0.0499(4) Uani 1 1 d . . .
H3 H 0.4736 0.2639 0.7479 0.060 Uiso 1 1 calc R . .
C4 C 0.6104(2) 0.18374(8) 0.8875(2) 0.0421(4) Uani 1 1 d . . .
C5 C 0.6026(2) 0.11389(8) 0.9039(2) 0.0473(4) Uani 1 1 d . . .
C2 C 0.3270(2) 0.18043(10) 0.6602(3) 0.0576(5) Uani 1 1 d . . .
H2 H 0.2329 0.2024 0.5750 0.069 Uiso 1 1 calc R . .
C1 C 0.3192(2) 0.11150(10) 0.6809(3) 0.0629(5) Uani 1 1 d . . .
H1 H 0.2198 0.0881 0.6118 0.076 Uiso 1 1 calc R . .
C11 C 0.8283(3) 0.44866(9) 1.0834(3) 0.0657(5) Uani 1 1 d . . .
H11A H 0.8331 0.4590 0.9567 0.099 Uiso 1 1 calc R . .
H11C H 0.9053 0.4781 1.1750 0.099 Uiso 1 1 calc R . .
H11B H 0.7112 0.4547 1.0878 0.099 Uiso 1 1 calc R . .
C8 C 0.7819(2) 0.20668(8) 1.0151(2) 0.0428(4) Uani 1 1 d . . .
C12 C 1.1611(2) 0.12827(11) 1.1290(3) 0.0662(5) Uani 1 1 d . . .
H12B H 1.1550 0.1592 1.0263 0.099 Uiso 1 1 calc R . .
H12A H 1.1390 0.0836 1.0781 0.099 Uiso 1 1 calc R . .
H12C H 1.2751 0.1302 1.2213 0.099 Uiso 1 1 calc R . .
C6 C 0.4584(2) 0.07712(10) 0.8038(3) 0.0578(5) Uani 1 1 d . . .
H6 H 0.4548 0.0308 0.8183 0.069 Uiso 1 1 calc R . .
C7 C 0.7701(2) 0.08927(8) 1.0363(2) 0.0490(4) 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
O4 0.0576(8) 0.0512(7) 0.0563(7) -0.0066(5) 0.0096(6) -0.0108(6)
O1 0.0659(9) 0.0525(7) 0.0726(8) 0.0110(6) 0.0113(7) 0.0024(6)
O2 0.0432(7) 0.0704(8) 0.0446(6) 0.0000(5) -0.0014(5) 0.0049(6)
O3 0.0636(8) 0.0542(7) 0.0608(8) 0.0028(6) -0.0030(7) -0.0051(6)
C9 0.0406(8) 0.0546(10) 0.0410(8) -0.0022(7) 0.0076(7) -0.0059(7)
N1 0.0384(7) 0.0540(8) 0.0459(7) 0.0015(6) 0.0021(6) 0.0002(6)
C10 0.0469(9) 0.0542(9) 0.0438(8) -0.0042(7) 0.0149(8) -0.0107(8)
C3 0.0416(9) 0.0537(9) 0.0512(9) -0.0040(7) 0.0091(8) 0.0012(7)
C4 0.0375(8) 0.0499(9) 0.0391(7) -0.0023(6) 0.0118(6) -0.0024(7)
C5 0.0450(9) 0.0501(9) 0.0465(8) 0.0010(7) 0.0133(7) -0.0043(7)
C2 0.0363(8) 0.0676(12) 0.0620(10) -0.0060(9) 0.0047(8) 0.0009(8)
C1 0.0407(9) 0.0711(12) 0.0702(12) -0.0100(10) 0.0068(9) -0.0113(9)
C11 0.0779(13) 0.0509(10) 0.0693(12) -0.0048(9) 0.0238(11) -0.0127(10)
C8 0.0398(8) 0.0520(9) 0.0358(7) 0.0001(6) 0.0103(7) -0.0011(7)
C12 0.0446(10) 0.0725(12) 0.0773(13) -0.0044(10) 0.0123(10) 0.0038(9)
C6 0.0507(10) 0.0548(10) 0.0658(11) -0.0033(8) 0.0145(9) -0.0112(8)
C7 0.0484(9) 0.0510(9) 0.0470(9) 0.0027(7) 0.0136(8) -0.0011(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
O4 C10 1.347(2) . ?
O4 C11 1.441(2) . ?
O1 C7 1.217(2) . ?
O2 N1 1.3768(17) . ?
O2 C12 1.443(2) . ?
O3 C10 1.209(2) . ?
C9 C8 1.344(2) . ?
C9 C10 1.462(2) . ?
C9 H9 0.9300 . ?
N1 C7 1.379(2) . ?
N1 C8 1.404(2) . ?
C3 C2 1.385(2) . ?
C3 C4 1.387(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.399(2) . ?
C4 C8 1.483(2) . ?
C5 C6 1.378(2) . ?
C5 C7 1.483(2) . ?
C2 C1 1.384(3) . ?
C2 H2 0.9300 . ?
C1 C6 1.385(3) . ?
C1 H1 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11C 0.9600 . ?
C11 H11B 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12C 0.9600 . ?
C6 H6 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
C10 O4 C11 115.84(14) . . ?
N1 O2 C12 109.55(12) . . ?
C8 C9 C10 127.39(16) . . ?
C8 C9 H9 116.3 . . ?
C10 C9 H9 116.3 . . ?
O2 N1 C7 122.02(13) . . ?
O2 N1 C8 122.20(13) . . ?
C7 N1 C8 115.03(14) . . ?
O3 C10 O4 122.47(16) . . ?
O3 C10 C9 128.11(16) . . ?
O4 C10 C9 109.42(14) . . ?
C2 C3 C4 118.20(17) . . ?
C2 C3 H3 120.9 . . ?
C4 C3 H3 120.9 . . ?
C3 C4 C5 119.36(15) . . ?
C3 C4 C8 132.57(15) . . ?
C5 C4 C8 108.05(13) . . ?
C6 C5 C4 122.36(16) . . ?
C6 C5 C7 128.41(16) . . ?
C4 C5 C7 109.21(14) . . ?
C1 C2 C3 121.90(17) . . ?
C1 C2 H2 119.0 . . ?
C3 C2 H2 119.0 . . ?
C2 C1 C6 120.43(16) . . ?
C2 C1 H1 119.8 . . ?
C6 C1 H1 119.8 . . ?
O4 C11 H11A 109.5 . . ?
O4 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
O4 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11C C11 H11B 109.5 . . ?
C9 C8 N1 120.91(15) . . ?
C9 C8 C4 135.34(16) . . ?
N1 C8 C4 103.67(13) . . ?
O2 C12 H12B 109.5 . . ?
O2 C12 H12A 109.5 . . ?
H12B C12 H12A 109.5 . . ?
O2 C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
C5 C6 C1 117.73(18) . . ?
C5 C6 H6 121.1 . . ?
C1 C6 H6 121.1 . . ?
O1 C7 N1 125.76(17) . . ?
O1 C7 C5 130.52(17) . . ?
N1 C7 C5 103.72(14) . . ?

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
C12 O2 N1 C7 85.36(19) . . . . ?
C12 O2 N1 C8 -105.06(17) . . . . ?
C11 O4 C10 O3 -1.8(2) . . . . ?
C11 O4 C10 C9 177.33(14) . . . . ?
C8 C9 C10 O3 -12.0(3) . . . . ?
C8 C9 C10 O4 168.90(16) . . . . ?
C2 C3 C4 C5 0.9(2) . . . . ?
C2 C3 C4 C8 179.18(16) . . . . ?
C3 C4 C5 C6 -1.8(2) . . . . ?
C8 C4 C5 C6 179.52(16) . . . . ?
C3 C4 C5 C7 176.67(14) . . . . ?
C8 C4 C5 C7 -2.03(17) . . . . ?
C4 C3 C2 C1 0.6(3) . . . . ?
C3 C2 C1 C6 -1.2(3) . . . . ?
C10 C9 C8 N1 -179.34(15) . . . . ?
C10 C9 C8 C4 -3.1(3) . . . . ?
O2 N1 C8 C9 1.0(2) . . . . ?
C7 N1 C8 C9 171.26(14) . . . . ?
O2 N1 C8 C4 -176.26(13) . . . . ?
C7 N1 C8 C4 -6.01(18) . . . . ?
C3 C4 C8 C9 9.5(3) . . . . ?
C5 C4 C8 C9 -172.03(18) . . . . ?
C3 C4 C8 N1 -173.83(16) . . . . ?
C5 C4 C8 N1 4.64(17) . . . . ?
C4 C5 C6 C1 1.2(3) . . . . ?
C7 C5 C6 C1 -176.97(17) . . . . ?
C2 C1 C6 C5 0.3(3) . . . . ?
O2 N1 C7 O1 -5.7(3) . . . . ?
C8 N1 C7 O1 -175.97(16) . . . . ?
O2 N1 C7 C5 175.08(13) . . . . ?
C8 N1 C7 C5 4.81(19) . . . . ?
C6 C5 C7 O1 -2.3(3) . . . . ?
C4 C5 C7 O1 179.37(18) . . . . ?
C6 C5 C7 N1 176.87(17) . . . . ?
C4 C5 C7 N1 -1.46(18) . . . . ?

_diffrn_measured_fraction_theta_max 0.970
_diffrn_reflns_theta_full        67.37
_diffrn_measured_fraction_theta_full 0.970
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.043