# Electronic Supplementary Material (ESI) for RSC Advances
# This journal is © The Royal Society of Chemistry 2013

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#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
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#  fide research purposes only. It may contain copyright material
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#  data retrieval see:
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data_junfeng071013

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H10 N2 O2'
_chemical_formula_sum            'C9 H10 N2 O2'
_chemical_formula_weight         178.19

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(1)/n

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                   4.44860(10)
_cell_length_b                   25.8691(6)
_cell_length_c                   7.4266(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.8670(10)
_cell_angle_gamma                90.00
_cell_volume                     850.19(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4355
_cell_measurement_theta_min      2.87
_cell_measurement_theta_max      28.27

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             380
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9793
_exptl_absorpt_correction_T_max  0.9945
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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            6929
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_sigmaI/netI    0.0226
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.57
_diffrn_reflns_theta_max         26.29
_reflns_number_total             1731
_reflns_number_gt                1483
_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^)+(0.0451P)^2^+0.3014P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1731
_refine_ls_number_parameters     120
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0345
_refine_ls_wR_factor_ref         0.0941
_refine_ls_wR_factor_gt          0.0892
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6262(2) 0.84365(4) 0.28193(12) 0.0207(2) Uani 1 1 d . . .
H1A H 0.7542 0.8675 0.2821 0.031 Uiso 1 1 calc R . .
O2 O 1.50108(19) 1.00180(3) 0.25847(12) 0.0192(2) Uani 1 1 d . . .
N1 N 1.2041(2) 0.95428(4) 0.41900(14) 0.0155(2) Uani 1 1 d . . .
H1B H 1.2766 0.9698 0.5197 0.019 Uiso 1 1 calc R . .
N2 N 0.9893(2) 0.91624(4) 0.42478(14) 0.0155(2) Uani 1 1 d . . .
C1 C 0.5600(3) 0.83489(5) 0.45400(17) 0.0165(3) Uani 1 1 d . . .
C2 C 0.3594(3) 0.79514(5) 0.48198(18) 0.0202(3) Uani 1 1 d . . .
H2 H 0.2743 0.7751 0.3823 0.024 Uiso 1 1 calc R . .
C3 C 0.2834(3) 0.78466(5) 0.65385(19) 0.0215(3) Uani 1 1 d . . .
H3 H 0.1480 0.7572 0.6717 0.026 Uiso 1 1 calc R . .
C4 C 0.4033(3) 0.81399(5) 0.80157(19) 0.0208(3) Uani 1 1 d . . .
H4 H 0.3484 0.8070 0.9194 0.025 Uiso 1 1 calc R . .
C5 C 0.6031(3) 0.85340(5) 0.77401(17) 0.0181(3) Uani 1 1 d . . .
H5 H 0.6853 0.8734 0.8744 0.022 Uiso 1 1 calc R . .
C6 C 0.6875(3) 0.86455(5) 0.60181(17) 0.0151(3) Uani 1 1 d . . .
C7 C 0.9077(3) 0.90510(5) 0.58096(17) 0.0151(3) Uani 1 1 d . . .
H7 H 0.9923 0.9236 0.6845 0.018 Uiso 1 1 calc R . .
C8 C 1.3047(3) 0.96810(5) 0.26058(17) 0.0154(3) Uani 1 1 d . . .
C9 C 1.1694(3) 0.94169(5) 0.09160(17) 0.0189(3) Uani 1 1 d . . .
H9A H 1.2627 0.9552 -0.0128 0.028 Uiso 1 1 calc R . .
H9B H 0.9513 0.9483 0.0751 0.028 Uiso 1 1 calc R . .
H9C H 1.2056 0.9044 0.1020 0.028 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 0.0232(5) 0.0228(5) 0.0168(5) -0.0023(4) 0.0044(4) -0.0066(4)
O2 0.0207(5) 0.0209(5) 0.0165(5) -0.0001(4) 0.0038(4) -0.0059(4)
N1 0.0154(5) 0.0173(5) 0.0140(5) -0.0023(4) 0.0019(4) -0.0039(4)
N2 0.0135(5) 0.0149(5) 0.0183(6) 0.0005(4) 0.0026(4) -0.0007(4)
C1 0.0142(6) 0.0173(6) 0.0182(7) -0.0002(5) 0.0028(5) 0.0025(4)
C2 0.0184(6) 0.0165(6) 0.0258(7) -0.0028(5) 0.0033(5) -0.0005(5)
C3 0.0169(6) 0.0164(6) 0.0319(8) 0.0034(5) 0.0065(5) -0.0009(5)
C4 0.0194(6) 0.0225(7) 0.0216(7) 0.0057(5) 0.0071(5) 0.0038(5)
C5 0.0166(6) 0.0206(6) 0.0172(6) 0.0008(5) 0.0014(5) 0.0024(5)
C6 0.0125(5) 0.0153(6) 0.0176(7) 0.0009(5) 0.0020(5) 0.0027(4)
C7 0.0139(5) 0.0166(6) 0.0147(6) -0.0011(5) 0.0012(5) 0.0015(4)
C8 0.0147(6) 0.0145(6) 0.0171(7) 0.0006(5) 0.0028(5) 0.0020(4)
C9 0.0215(6) 0.0210(6) 0.0146(6) -0.0007(5) 0.0034(5) -0.0024(5)

_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 1.3594(15) . ?
O1 H1A 0.8400 . ?
O2 C8 1.2354(15) . ?
N1 C8 1.3492(16) . ?
N1 N2 1.3751(14) . ?
N1 H1B 0.8800 . ?
N2 C7 1.2832(16) . ?
C1 C2 1.3910(17) . ?
C1 C6 1.4100(17) . ?
C2 C3 1.3803(19) . ?
C2 H2 0.9500 . ?
C3 C4 1.3944(19) . ?
C3 H3 0.9500 . ?
C4 C5 1.3814(18) . ?
C4 H4 0.9500 . ?
C5 C6 1.3991(18) . ?
C5 H5 0.9500 . ?
C6 C7 1.4543(16) . ?
C7 H7 0.9500 . ?
C8 C9 1.4998(17) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 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 H1A 109.5 . . ?
C8 N1 N2 120.69(10) . . ?
C8 N1 H1B 119.7 . . ?
N2 N1 H1B 119.7 . . ?
C7 N2 N1 116.78(10) . . ?
O1 C1 C2 117.88(11) . . ?
O1 C1 C6 122.19(11) . . ?
C2 C1 C6 119.94(12) . . ?
C3 C2 C1 120.33(12) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 120.69(12) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 119.02(12) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 121.63(12) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C5 C6 C1 118.38(11) . . ?
C5 C6 C7 119.51(11) . . ?
C1 C6 C7 122.09(11) . . ?
N2 C7 C6 120.94(11) . . ?
N2 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
O2 C8 N1 119.75(11) . . ?
O2 C8 C9 122.33(11) . . ?
N1 C8 C9 117.92(10) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.29
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.041
_database_code_depnum_ccdc_archive 'CCDC 970383'