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


data_global
_journal_name_full               J.Mater.Chem.
_journal_coden_cambridge         1145
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_address     
;
Dr. Guoping Yong
Department of Chemistry,
University of Science and Technology of China,
Hefei, 230026, China,
;

_publ_contact_author_email       gpyong@ustc.edu.cn

_publ_contact_author_name        'Dr. Guoping Yong'
loop_
_publ_author_name
'Guoping Yong'
'Yiman Zhang'
'Wenlong She'
'Yingzhou Li'

data_1
_database_code_depnum_ccdc_archive 'CCDC 845170'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H8 N2 O4'
_chemical_formula_weight         208.17

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           monoclinic
_symmetry_space_group_name_H-M   P2/c

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

_cell_length_a                   6.8155(14)
_cell_length_b                   11.734(2)
_cell_length_c                   11.551(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.23(3)
_cell_angle_gamma                90.00
_cell_volume                     899.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.23
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.530
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             428
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.965
_exptl_absorpt_correction_T_max  0.972
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3671
_diffrn_reflns_av_R_equivalents  0.0627
_diffrn_reflns_av_sigmaI/netI    0.0731
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.07
_diffrn_reflns_theta_max         24.71
_reflns_number_total             1522
_reflns_number_gt                815
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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^)+(0.1337P)^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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1522
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1529
_refine_ls_R_factor_gt           0.0923
_refine_ls_wR_factor_ref         0.2717
_refine_ls_wR_factor_gt          0.2330
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_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
C1 C 0.7503(7) 0.7499(4) 0.1839(4) 0.0536(13) Uani 1 1 d . . .
C2 C 0.7396(8) 0.6509(5) 0.2486(5) 0.0683(16) Uani 1 1 d . . .
H2A H 0.7296 0.6542 0.3275 0.082 Uiso 1 1 calc R . .
C3 C 0.7441(9) 0.5503(5) 0.1934(6) 0.0790(18) Uani 1 1 d . . .
H3A H 0.7334 0.4832 0.2343 0.095 Uiso 1 1 calc R . .
C4 C 0.7647(9) 0.5447(5) 0.0751(6) 0.0844(19) Uani 1 1 d . . .
H4A H 0.7728 0.4742 0.0398 0.101 Uiso 1 1 calc R . .
C5 C 0.7726(9) 0.6399(5) 0.0131(5) 0.0765(18) Uani 1 1 d . . .
H5A H 0.7824 0.6363 -0.0658 0.092 Uiso 1 1 calc R . .
C6 C 0.7684(7) 0.8540(4) 0.0255(4) 0.0558(14) Uani 1 1 d . . .
H6A H 0.7770 0.8751 -0.0508 0.067 Uiso 1 1 calc R . .
C7 C 0.7557(7) 0.9246(4) 0.1155(4) 0.0508(13) Uani 1 1 d . . .
C8 C 0.7523(7) 1.0494(4) 0.1258(4) 0.0551(14) Uani 1 1 d . . .
C9 C 0.7466(8) 1.1245(5) 0.0146(4) 0.0609(14) Uani 1 1 d . . .
N1 N 0.7469(6) 0.8599(3) 0.2131(3) 0.0546(12) Uani 1 1 d . . .
N2 N 0.7659(6) 0.7444(3) 0.0683(3) 0.0578(12) Uani 1 1 d . . .
O1 O 0.7501(7) 1.0936(3) 0.2197(3) 0.0898(15) Uani 1 1 d . . .
O2 O 0.7689(8) 1.2256(3) 0.0295(4) 0.1053(17) Uani 1 1 d . . .
O3 O 0.7213(6) 1.0696(3) -0.0795(3) 0.0798(13) Uani 1 1 d . . .
O4 O 1.0000 0.3219(6) 0.2500 0.119(3) Uani 1 2 d S . .
O4A O 1.5000 0.2978(5) 0.2500 0.121(2) Uani 1 2 d S . .
H1 H 0.724(8) 0.884(4) 0.298(5) 0.084(16) Uiso 1 1 d . . .
H2 H 0.935(14) 0.289(6) 0.186(8) 0.16(3) Uiso 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
C1 0.047(3) 0.062(3) 0.051(3) 0.000(2) 0.009(2) -0.002(2)
C2 0.071(4) 0.071(4) 0.065(3) 0.009(3) 0.019(3) 0.006(3)
C3 0.090(5) 0.061(4) 0.087(5) 0.008(3) 0.023(4) 0.005(3)
C4 0.104(5) 0.055(4) 0.092(5) -0.005(3) 0.019(4) 0.011(3)
C5 0.091(4) 0.073(4) 0.064(4) -0.021(3) 0.015(3) 0.009(3)
C6 0.062(3) 0.062(3) 0.044(3) -0.001(2) 0.013(2) -0.003(3)
C7 0.053(3) 0.063(3) 0.039(3) -0.002(2) 0.015(2) -0.002(2)
C8 0.069(3) 0.056(3) 0.043(3) -0.003(2) 0.019(2) -0.008(3)
C9 0.067(3) 0.069(4) 0.047(3) -0.001(3) 0.014(3) -0.002(3)
N1 0.067(3) 0.055(3) 0.044(2) -0.0008(19) 0.018(2) 0.001(2)
N2 0.070(3) 0.055(3) 0.049(2) -0.0089(19) 0.016(2) 0.002(2)
O1 0.166(4) 0.060(2) 0.050(2) -0.0074(18) 0.037(2) -0.013(2)
O2 0.186(5) 0.053(3) 0.074(3) 0.004(2) 0.025(3) -0.009(3)
O3 0.116(3) 0.084(3) 0.043(2) 0.0021(18) 0.026(2) -0.006(2)
O4 0.142(7) 0.050(4) 0.141(8) 0.000 -0.017(6) 0.000
O4A 0.123(6) 0.081(4) 0.150(6) 0.000 0.013(5) 0.000

_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 N1 1.336(6) . ?
C1 N2 1.366(6) . ?
C1 C2 1.391(7) . ?
C2 C3 1.345(7) . ?
C3 C4 1.407(8) . ?
C4 C5 1.334(8) . ?
C5 N2 1.387(6) . ?
C6 C7 1.348(6) . ?
C6 N2 1.379(6) . ?
C7 N1 1.372(6) . ?
C7 C8 1.469(7) . ?
C8 O1 1.205(5) . ?
C8 C9 1.551(7) . ?
C9 O2 1.204(6) . ?
C9 O3 1.241(6) . ?

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
N1 C1 N2 107.6(4) . . ?
N1 C1 C2 131.7(4) . . ?
N2 C1 C2 120.7(5) . . ?
C3 C2 C1 117.9(5) . . ?
C2 C3 C4 121.3(5) . . ?
C5 C4 C3 120.5(5) . . ?
C4 C5 N2 119.0(5) . . ?
C7 C6 N2 106.8(4) . . ?
C6 C7 N1 108.4(4) . . ?
C6 C7 C8 132.8(4) . . ?
N1 C7 C8 118.7(4) . . ?
O1 C8 C7 120.3(4) . . ?
O1 C8 C9 119.8(5) . . ?
C7 C8 C9 119.8(4) . . ?
O2 C9 O3 128.6(5) . . ?
O2 C9 C8 117.6(5) . . ?
O3 C9 C8 113.7(5) . . ?
C1 N1 C7 108.7(4) . . ?
C1 N2 C6 108.5(4) . . ?
C1 N2 C5 120.6(4) . . ?
C6 N2 C5 130.9(4) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        24.71
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.507
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.133