# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_20160628zcj_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1499990'
_audit_update_record             
;
2016-08-19 deposited with the CCDC.
2016-10-07 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 H10 N2 O2'
_chemical_formula_weight         226.23

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   P2(1)2(1)2(1)

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

_cell_length_a                   5.2167(7)
_cell_length_b                   10.4562(12)
_cell_length_c                   18.815(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1026.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4060
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      27.74

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             472
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9722
_exptl_absorpt_correction_T_max  0.9781
_exptl_absorpt_process_details   SADABS

_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       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6066
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_sigmaI/netI    0.0302
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.23
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1816
_reflns_number_gt                1714
_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-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0363P)²+0.2976P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1.3(15)
_refine_ls_number_reflns         1816
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0350
_refine_ls_wR_factor_ref         0.0838
_refine_ls_wR_factor_gt          0.0828
_refine_ls_goodness_of_fit_ref   1.146
_refine_ls_restrained_S_all      1.146
_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
O2 O 0.8041(3) 0.31444(12) 0.62019(7) 0.0233(3) Uani 1 1 d . . .
O1 O 0.5968(3) 0.95123(13) 0.67466(7) 0.0262(3) Uani 1 1 d . . .
N2 N 0.8039(3) 0.57173(14) 0.66503(8) 0.0192(4) Uani 1 1 d . . .
N1 N 0.7645(3) 0.69819(14) 0.67768(8) 0.0203(4) Uani 1 1 d . . .
C5 C 0.5716(4) 0.73256(17) 0.63414(9) 0.0177(4) Uani 1 1 d . . .
C7 C 0.2963(4) 0.59566(17) 0.54020(9) 0.0200(4) Uani 1 1 d . . .
H7 H 0.1850 0.6577 0.5228 0.024 Uiso 1 1 calc R . .
C12 C 0.9912(4) 0.48666(18) 0.69707(10) 0.0221(4) Uani 1 1 d . . .
H12A H 1.0191 0.5095 0.7464 0.026 Uiso 1 1 calc R . .
H12B H 1.1534 0.4924 0.6720 0.026 Uiso 1 1 calc R . .
C13 C 0.6418(3) 0.52684(18) 0.61502(9) 0.0176(4) Uani 1 1 d . . .
C6 C 0.4826(4) 0.62583(17) 0.59223(9) 0.0180(4) Uani 1 1 d . . .
C4 C 0.4686(4) 0.86123(17) 0.63441(9) 0.0191(4) Uani 1 1 d . . .
C10 C 0.6307(4) 0.40018(18) 0.59161(10) 0.0196(4) Uani 1 1 d . . .
C8 C 0.2849(4) 0.47139(18) 0.51606(10) 0.0225(4) Uani 1 1 d . . .
H8 H 0.1634 0.4508 0.4817 0.027 Uiso 1 1 calc R . .
C9 C 0.4507(4) 0.37266(18) 0.54121(10) 0.0224(4) Uani 1 1 d . . .
H9 H 0.4362 0.2900 0.5233 0.027 Uiso 1 1 calc R . .
C1 C 0.2549(4) 1.04549(18) 0.62505(10) 0.0256(5) Uani 1 1 d . . .
H1 H 0.1339 1.1067 0.6123 0.031 Uiso 1 1 calc R . .
C3 C 0.2601(4) 0.91465(18) 0.60391(10) 0.0240(5) Uani 1 1 d . . .
H3 H 0.1422 0.8737 0.5746 0.029 Uiso 1 1 calc R . .
C11 C 0.8835(4) 0.35140(19) 0.69172(10) 0.0250(5) Uani 1 1 d . . .
H11A H 1.0127 0.2916 0.7082 0.030 Uiso 1 1 calc R . .
H11B H 0.7371 0.3443 0.7233 0.030 Uiso 1 1 calc R . .
C2 C 0.4590(4) 1.06252(18) 0.66702(11) 0.0280(5) Uani 1 1 d . . .
H2 H 0.5023 1.1398 0.6883 0.034 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
O2 0.0256(8) 0.0206(7) 0.0236(7) 0.0014(5) 0.0001(6) 0.0047(6)
O1 0.0280(8) 0.0209(8) 0.0297(7) -0.0052(6) -0.0023(7) -0.0044(6)
N2 0.0177(9) 0.0200(9) 0.0199(8) 0.0027(6) -0.0004(7) -0.0006(7)
N1 0.0210(9) 0.0204(9) 0.0194(8) 0.0008(6) -0.0008(8) -0.0036(7)
C5 0.0172(10) 0.0212(9) 0.0146(8) 0.0021(7) 0.0003(8) -0.0032(7)
C7 0.0204(10) 0.0226(10) 0.0171(9) 0.0029(7) -0.0010(8) -0.0005(8)
C12 0.0173(10) 0.0297(11) 0.0192(9) 0.0024(8) -0.0025(8) 0.0023(9)
C13 0.0151(10) 0.0217(10) 0.0161(9) 0.0018(7) 0.0018(8) -0.0015(8)
C6 0.0185(10) 0.0180(9) 0.0176(9) 0.0015(7) 0.0035(8) -0.0033(8)
C4 0.0224(10) 0.0192(9) 0.0156(9) -0.0012(7) 0.0022(8) -0.0062(8)
C10 0.0188(10) 0.0212(11) 0.0189(9) 0.0034(7) 0.0042(8) 0.0004(8)
C8 0.0234(10) 0.0250(10) 0.0191(9) -0.0003(7) -0.0055(9) -0.0052(9)
C9 0.0250(11) 0.0190(10) 0.0232(10) -0.0023(8) 0.0010(9) -0.0044(9)
C1 0.0297(12) 0.0224(10) 0.0247(10) 0.0018(7) 0.0051(10) 0.0050(10)
C3 0.0252(12) 0.0223(10) 0.0246(10) -0.0013(8) -0.0033(9) -0.0004(9)
C11 0.0251(11) 0.0292(12) 0.0208(10) 0.0056(8) -0.0006(9) 0.0048(9)
C2 0.0338(12) 0.0149(10) 0.0353(11) -0.0044(8) 0.0066(11) -0.0033(9)

_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
O2 C10 1.382(2) . ?
O2 C11 1.460(2) . ?
O1 C2 1.375(2) . ?
O1 C4 1.381(2) . ?
N2 C13 1.349(2) . ?
N2 N1 1.359(2) . ?
N2 C12 1.452(2) . ?
N1 C5 1.346(2) . ?
C5 C6 1.443(3) . ?
C5 C4 1.449(3) . ?
C7 C8 1.378(3) . ?
C7 C6 1.415(3) . ?
C7 H7 0.9300 . ?
C12 C11 1.525(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C6 1.395(3) . ?
C13 C10 1.397(3) . ?
C4 C3 1.351(3) . ?
C10 C9 1.365(3) . ?
C8 C9 1.428(3) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C1 C2 1.338(3) . ?
C1 C3 1.425(3) . ?
C1 H1 0.9300 . ?
C3 H3 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C2 H2 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 O2 C11 111.87(14) . . ?
C2 O1 C4 105.44(15) . . ?
C13 N2 N1 111.45(15) . . ?
C13 N2 C12 119.87(16) . . ?
N1 N2 C12 128.68(16) . . ?
C5 N1 N2 105.44(14) . . ?
N1 C5 C6 111.49(16) . . ?
N1 C5 C4 121.52(16) . . ?
C6 C5 C4 126.94(16) . . ?
C8 C7 C6 117.89(17) . . ?
C8 C7 H7 121.1 . . ?
C6 C7 H7 121.1 . . ?
N2 C12 C11 107.01(16) . . ?
N2 C12 H12A 110.3 . . ?
C11 C12 H12A 110.3 . . ?
N2 C12 H12B 110.3 . . ?
C11 C12 H12B 110.3 . . ?
H12A C12 H12B 108.6 . . ?
N2 C13 C6 109.24(16) . . ?
N2 C13 C10 125.14(17) . . ?
C6 C13 C10 125.60(17) . . ?
C13 C6 C7 117.14(16) . . ?
C13 C6 C5 102.38(16) . . ?
C7 C6 C5 140.47(17) . . ?
C3 C4 O1 109.94(16) . . ?
C3 C4 C5 132.93(18) . . ?
O1 C4 C5 117.09(16) . . ?
C9 C10 O2 125.70(17) . . ?
C9 C10 C13 116.57(17) . . ?
O2 C10 C13 117.72(17) . . ?
C7 C8 C9 123.14(18) . . ?
C7 C8 H8 118.4 . . ?
C9 C8 H8 118.4 . . ?
C10 C9 C8 119.64(17) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C2 C1 C3 106.09(18) . . ?
C2 C1 H1 127.0 . . ?
C3 C1 H1 127.0 . . ?
C4 C3 C1 107.10(18) . . ?
C4 C3 H3 126.4 . . ?
C1 C3 H3 126.4 . . ?
O2 C11 C12 114.25(15) . . ?
O2 C11 H11A 108.7 . . ?
C12 C11 H11A 108.7 . . ?
O2 C11 H11B 108.7 . . ?
C12 C11 H11B 108.7 . . ?
H11A C11 H11B 107.6 . . ?
C1 C2 O1 111.42(16) . . ?
C1 C2 H2 124.3 . . ?
O1 C2 H2 124.3 . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.050
