# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_g130925b
_database_code_depnum_ccdc_archive 'CCDC 1040947'
_audit_update_record             
;
2014-12-24 deposited with the CCDC.
2015-02-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H12 N2 O'
_chemical_formula_weight         212.25

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           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab '

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                   6.3920(4)
_cell_length_b                   8.4041(5)
_cell_length_c                   20.1646(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1083.22(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1399
_cell_measurement_theta_min      3.8590
_cell_measurement_theta_max      27.1980

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.5000
_exptl_crystal_size_mid          0.4000
_exptl_crystal_size_min          0.2000
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             448
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.39293
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_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  'Xcalibur, Atlas, Gemini'
_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            3998
_diffrn_reflns_av_R_equivalents  0.1054
_diffrn_reflns_av_sigmaI/netI    0.1213
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.16
_diffrn_reflns_theta_max         29.26
_reflns_number_total             2386
_reflns_number_gt                1678
_reflns_threshold_expression     >2sigma(I)


_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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 F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.1150P)²+0.0000P] where P=(Fo²+2Fc²)/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     SHELXL
_refine_ls_extinction_coef       0.050(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -5(4)
_refine_ls_number_reflns         2386
_refine_ls_number_parameters     150
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1075
_refine_ls_R_factor_gt           0.0887
_refine_ls_wR_factor_ref         0.2427
_refine_ls_wR_factor_gt          0.2151
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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 0.8566(5) 0.7414(3) 0.00211(14) 0.0440(8) Uani 1 1 d . . .
N1 N 0.8334(5) 0.9668(4) 0.06280(14) 0.0306(8) Uani 1 1 d . . .
N2 N 0.6424(6) 0.9182(4) 0.09103(16) 0.0318(8) Uani 1 1 d . . .
C1 C 0.9054(6) 1.1245(5) 0.07772(16) 0.0293(9) Uani 1 1 d . . .
C2 C 1.1108(6) 1.1666(5) 0.06805(18) 0.0363(10) Uani 1 1 d . . .
H2 H 1.2075 1.0907 0.0543 0.044 Uiso 1 1 calc R . .
C3 C 1.1744(8) 1.3236(5) 0.07888(19) 0.0436(11) Uani 1 1 d . . .
H3 H 1.3122 1.3533 0.0708 0.052 Uiso 1 1 calc R . .
C4 C 1.0322(8) 1.4344(5) 0.1015(2) 0.0449(12) Uani 1 1 d . . .
H4 H 1.0744 1.5389 0.1087 0.054 Uiso 1 1 calc R . .
C5 C 0.8290(7) 1.3914(5) 0.11346(19) 0.0413(10) Uani 1 1 d . . .
H5 H 0.7344 1.4666 0.1292 0.050 Uiso 1 1 calc R . .
C6 C 0.7632(7) 1.2360(5) 0.10227(18) 0.0353(10) Uani 1 1 d . . .
H6 H 0.6257 1.2066 0.1111 0.042 Uiso 1 1 calc R . .
C7 C 0.9224(7) 0.8755(5) 0.01602(19) 0.0344(10) Uani 1 1 d . . .
H7 H 1.0380 0.9146 -0.0068 0.041 Uiso 1 1 calc R . .
C8 C 0.6581(6) 0.8209(4) 0.14838(17) 0.0300(9) Uani 1 1 d . . .
C9 C 0.8355(7) 0.8136(5) 0.18747(17) 0.0359(9) Uani 1 1 d . . .
H9 H 0.9544 0.8710 0.1758 0.043 Uiso 1 1 calc R . .
C10 C 0.8351(8) 0.7206(5) 0.24386(19) 0.0448(11) Uani 1 1 d . . .
H10 H 0.9547 0.7150 0.2700 0.054 Uiso 1 1 calc R . .
C11 C 0.6590(9) 0.6358(6) 0.2618(2) 0.0501(12) Uani 1 1 d . . .
H11 H 0.6599 0.5739 0.3001 0.060 Uiso 1 1 calc R . .
C12 C 0.4834(8) 0.6428(6) 0.2233(2) 0.0506(13) Uani 1 1 d . . .
H12 H 0.3650 0.5850 0.2350 0.061 Uiso 1 1 calc R . .
C13 C 0.4819(7) 0.7362(5) 0.16671(19) 0.0387(10) Uani 1 1 d . . .
H13 H 0.3616 0.7420 0.1409 0.046 Uiso 1 1 calc R . .
H2A H 0.575(8) 0.887(7) 0.058(2) 0.049(15) 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
O1 0.0512(19) 0.0179(14) 0.0629(15) -0.0124(13) 0.0072(13) 0.0046(15)
N1 0.0374(19) 0.0115(15) 0.0430(15) -0.0032(12) 0.0092(14) -0.0003(14)
N2 0.0332(19) 0.0158(16) 0.0465(18) -0.0054(14) 0.0017(16) -0.0001(15)
C1 0.037(2) 0.0127(18) 0.0383(17) -0.0008(15) 0.0041(16) -0.0029(15)
C2 0.039(2) 0.023(2) 0.0464(19) -0.0006(17) -0.0010(18) 0.0060(18)
C3 0.050(3) 0.025(2) 0.056(2) 0.0049(19) 0.006(2) -0.012(2)
C4 0.061(3) 0.0088(19) 0.065(3) -0.0017(19) -0.004(2) 0.000(2)
C5 0.047(3) 0.013(2) 0.064(2) -0.0085(18) 0.002(2) 0.0034(19)
C6 0.039(2) 0.020(2) 0.047(2) -0.0052(18) 0.0031(16) 0.0009(19)
C7 0.042(2) 0.013(2) 0.048(2) -0.0040(17) 0.0111(18) 0.0016(16)
C8 0.041(2) 0.0091(17) 0.0400(17) -0.0060(15) 0.0063(17) 0.0014(17)
C9 0.041(2) 0.023(2) 0.0440(19) -0.0049(17) 0.0028(18) -0.007(2)
C10 0.059(3) 0.030(2) 0.046(2) -0.0060(18) -0.003(2) 0.005(2)
C11 0.077(4) 0.023(2) 0.050(2) 0.0059(19) 0.007(3) -0.005(3)
C12 0.061(3) 0.028(2) 0.063(3) 0.001(2) 0.018(3) -0.004(2)
C13 0.038(2) 0.026(2) 0.052(2) -0.0116(19) 0.0038(18) -0.001(2)

_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 C7 1.235(5) . ?
N1 C7 1.343(5) . ?
N1 N2 1.407(4) . ?
N1 C1 1.435(5) . ?
N2 C8 1.420(5) . ?
N2 H2A 0.83(5) . ?
C1 C2 1.374(6) . ?
C1 C6 1.396(5) . ?
C2 C3 1.398(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.379(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.370(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.390(6) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C13 1.382(5) . ?
C8 C9 1.382(6) . ?
C9 C10 1.380(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.381(7) . ?
C10 H10 0.9300 . ?
C11 C12 1.366(7) . ?
C11 H11 0.9300 . ?
C12 C13 1.385(6) . ?
C12 H12 0.9300 . ?
C13 H13 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
C7 N1 N2 119.1(3) . . ?
C7 N1 C1 122.6(3) . . ?
N2 N1 C1 117.5(3) . . ?
N1 N2 C8 115.8(3) . . ?
N1 N2 H2A 103(3) . . ?
C8 N2 H2A 120(4) . . ?
C2 C1 C6 120.0(4) . . ?
C2 C1 N1 121.0(4) . . ?
C6 C1 N1 119.0(3) . . ?
C1 C2 C3 119.9(4) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C4 C3 C2 119.8(5) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C5 C4 C3 120.3(4) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 120.4(4) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C1 119.4(4) . . ?
C5 C6 H6 120.3 . . ?
C1 C6 H6 120.3 . . ?
O1 C7 N1 122.5(4) . . ?
O1 C7 H7 118.8 . . ?
N1 C7 H7 118.8 . . ?
C13 C8 C9 119.6(3) . . ?
C13 C8 N2 117.2(3) . . ?
C9 C8 N2 123.2(3) . . ?
C10 C9 C8 119.6(4) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C9 C10 C11 120.7(4) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C12 C11 C10 119.9(4) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C11 C12 C13 119.9(4) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C8 C13 C12 120.4(4) . . ?
C8 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.397
_refine_diff_density_min         -0.388
_refine_diff_density_rms         0.094
