# Electronic Supplementary Material (ESI) for Faraday Discussions.
# 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_cadmbz
_database_code_depnum_ccdc_archive 'CCDC 1486589'
_audit_update_record             
;
2016-06-18 deposited with the CCDC.
2016-08-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          480
_chemical_formula_moiety         CHNO
_chemical_formula_sum            'C12 H12 N2 O3'
_chemical_formula_weight         232.24

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   'P 1 21/n 1'

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                   10.5310(11)
_cell_length_b                   15.6321(15)
_cell_length_c                   13.7351(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.071(10)
_cell_angle_gamma                90.00
_cell_volume                     2255.4(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1678
_cell_measurement_theta_min      2.9944
_cell_measurement_theta_max      29.1879

_exptl_crystal_description       rectangular
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             854
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.86613
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   multi-scan

_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, Eos'
_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            10852
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_sigmaI/netI    0.0554
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.00
_diffrn_reflns_theta_max         29.25
_reflns_number_total             5167
_reflns_number_gt                2669
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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 > 2σ(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)+(0.0969P)²+3.0795P] 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_number_reflns         5167
_refine_ls_number_parameters     311
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1469
_refine_ls_R_factor_gt           0.0818
_refine_ls_wR_factor_ref         0.2624
_refine_ls_wR_factor_gt          0.2164
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_restrained_S_all      0.981
_refine_ls_shift/su_max          0.035
_refine_ls_shift/su_mean         0.011

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 0.6483(3) 0.27246(17) 0.1110(2) 0.0611(8) Uani 1 1 d . . .
O2 O 0.2713(2) 0.05879(17) 0.3657(2) 0.0527(7) Uani 1 1 d . . .
O5 O 0.7330(2) -0.02329(17) 0.1365(2) 0.0551(8) Uani 1 1 d . . .
O6 O 0.4641(2) -0.24409(18) 0.1387(2) 0.0665(9) Uani 1 1 d . . .
O1 O 0.3577(3) -0.23677(18) 0.3916(2) 0.0663(9) Uani 1 1 d . . .
N2 N 0.7476(3) 0.2760(2) 0.3609(3) 0.0713(12) Uani 1 1 d . . .
H2A H 0.7522 0.3307 0.3565 0.086 Uiso 1 1 calc R . .
H2B H 0.8161 0.2458 0.3656 0.086 Uiso 1 1 calc R . .
N1 N 0.8506(3) 0.0683(2) 0.3895(3) 0.0704(11) Uani 1 1 d . . .
O3 O 0.5345(3) 0.27947(18) 0.3538(3) 0.0711(9) Uani 1 1 d . . .
N3 N 0.1545(3) -0.0304(2) 0.1204(3) 0.0729(12) Uani 1 1 d . . .
C20 C 0.3710(3) -0.1073(2) 0.1292(3) 0.0412(9) Uani 1 1 d . . .
C14 C 0.6506(3) 0.0434(2) 0.1275(3) 0.0382(8) Uani 1 1 d . . .
C9 C 0.7518(3) 0.1002(2) 0.3799(3) 0.0456(9) Uani 1 1 d . . .
C21 C 0.2515(4) -0.0632(3) 0.1247(3) 0.0480(10) Uani 1 1 d . . .
C13 C 0.5184(3) 0.0214(2) 0.1240(3) 0.0378(8) Uani 1 1 d . . .
C5 C 0.5358(3) -0.1388(2) 0.3832(3) 0.0493(10) Uani 1 1 d . . .
H5 H 0.5957 -0.1826 0.3867 0.059 Uiso 1 1 calc R . .
C8 C 0.6333(3) 0.1427(2) 0.3682(3) 0.0410(9) Uani 1 1 d . . .
N4 N 0.2513(3) -0.2384(2) 0.1361(3) 0.0679(11) Uani 1 1 d . . .
H4A H 0.2442 -0.2931 0.1390 0.082 Uiso 1 1 calc R . .
H4B H 0.1844 -0.2067 0.1337 0.082 Uiso 1 1 calc R . .
C22 C 0.3670(3) -0.2024(2) 0.1354(3) 0.0485(10) Uani 1 1 d . . .
C7 C 0.5201(3) 0.1019(2) 0.3659(3) 0.0405(9) Uani 1 1 d . . .
H7 H 0.4504 0.1385 0.3594 0.049 Uiso 1 1 calc R . .
C6 C 0.5728(3) -0.0544(2) 0.3771(3) 0.0443(9) Uani 1 1 d . . .
H6 H 0.6592 -0.0421 0.3766 0.053 Uiso 1 1 calc R . .
C17 C 0.4696(4) 0.1739(3) 0.1104(3) 0.0509(10) Uani 1 1 d . . .
H17 H 0.4090 0.2172 0.1049 0.061 Uiso 1 1 calc R . .
C2 C 0.3551(3) -0.0078(2) 0.3717(3) 0.0385(8) Uani 1 1 d . . .
C16 C 0.5990(4) 0.1926(2) 0.1147(3) 0.0457(9) Uani 1 1 d . . .
C1 C 0.4859(3) 0.0134(2) 0.3715(3) 0.0375(8) Uani 1 1 d . . .
C18 C 0.4338(3) 0.0892(3) 0.1147(3) 0.0483(10) Uani 1 1 d . . .
H18 H 0.3472 0.0769 0.1111 0.058 Uiso 1 1 calc R . .
C19 C 0.4843(3) -0.0677(2) 0.1287(3) 0.0401(8) Uani 1 1 d . . .
C4 C 0.4065(4) -0.1567(2) 0.3840(3) 0.0459(9) Uani 1 1 d . . .
C24 C 0.8675(3) -0.0051(3) 0.1385(3) 0.0603(12) Uani 1 1 d . . .
H24A H 0.9147 -0.0575 0.1456 0.090 Uiso 1 1 calc R . .
H24B H 0.8911 0.0320 0.1925 0.090 Uiso 1 1 calc R . .
H24C H 0.8863 0.0225 0.0787 0.090 Uiso 1 1 calc R . .
C10 C 0.6350(3) 0.2380(3) 0.3605(3) 0.0501(10) Uani 1 1 d . . .
C23 C 0.5614(5) 0.3427(3) 0.1057(4) 0.0743(14) Uani 1 1 d . . .
H23A H 0.6079 0.3953 0.1028 0.111 Uiso 1 1 calc R . .
H23B H 0.5132 0.3428 0.1625 0.111 Uiso 1 1 calc R . .
H23C H 0.5045 0.3372 0.0482 0.111 Uiso 1 1 calc R . .
C3 C 0.3166(3) -0.0922(2) 0.3780(3) 0.0451(9) Uani 1 1 d . . .
H3 H 0.2305 -0.1054 0.3782 0.054 Uiso 1 1 calc R . .
C12 C 0.1387(3) 0.0401(3) 0.3673(3) 0.0565(11) Uani 1 1 d . . .
H12A H 0.0909 0.0923 0.3621 0.085 Uiso 1 1 calc R . .
H12B H 0.1232 0.0119 0.4274 0.085 Uiso 1 1 calc R . .
H12C H 0.1130 0.0034 0.3134 0.085 Uiso 1 1 calc R . .
C11 C 0.4434(5) -0.3078(3) 0.3910(4) 0.0795(15) Uani 1 1 d . . .
H11A H 0.3967 -0.3601 0.3970 0.119 Uiso 1 1 calc R . .
H11B H 0.5063 -0.3028 0.4449 0.119 Uiso 1 1 calc R . .
H11C H 0.4846 -0.3082 0.3309 0.119 Uiso 1 1 calc R . .
C15 C 0.6881(3) 0.1270(2) 0.1229(3) 0.0434(9) Uani 1 1 d . . .
H15 H 0.7744 0.1401 0.1254 0.052 Uiso 1 1 calc R . .
H19 H 0.558(3) -0.108(2) 0.129(2) 0.040(10) Uiso 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 C16 1.355(4) . ?
O4 C23 1.428(5) . ?
O2 C2 1.364(4) . ?
O2 C12 1.428(4) . ?
O5 C14 1.355(4) . ?
O5 C24 1.444(4) . ?
O6 C22 1.211(4) . ?
O1 C4 1.359(5) . ?
O1 C11 1.432(5) . ?
N2 C10 1.326(5) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
N1 C9 1.153(5) . ?
O3 C10 1.239(4) . ?
N3 C21 1.140(5) . ?
C20 C19 1.344(5) . ?
C20 C21 1.433(5) . ?
C20 C22 1.490(5) . ?
C14 C15 1.368(5) . ?
C14 C13 1.432(5) . ?
C9 C8 1.412(5) . ?
C13 C18 1.384(5) . ?
C13 C19 1.441(5) . ?
C5 C6 1.379(5) . ?
C5 C4 1.391(5) . ?
C5 H5 0.9300 . ?
C8 C7 1.351(5) . ?
C8 C10 1.495(5) . ?
N4 C22 1.342(4) . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8600 . ?
C7 C1 1.433(5) . ?
C7 H7 0.9300 . ?
C6 C1 1.399(5) . ?
C6 H6 0.9300 . ?
C17 C18 1.378(5) . ?
C17 C16 1.391(5) . ?
C17 H17 0.9300 . ?
C2 C3 1.384(5) . ?
C2 C1 1.417(5) . ?
C16 C15 1.389(5) . ?
C18 H18 0.9300 . ?
C19 H19 1.00(4) . ?
C4 C3 1.381(5) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C3 H3 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C15 H15 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
C16 O4 C23 117.7(3) . . ?
C2 O2 C12 118.1(3) . . ?
C14 O5 C24 118.1(3) . . ?
C4 O1 C11 118.1(3) . . ?
C10 N2 H2A 120.0 . . ?
C10 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C19 C20 C21 123.7(4) . . ?
C19 C20 C22 119.2(3) . . ?
C21 C20 C22 117.0(3) . . ?
O5 C14 C15 123.6(3) . . ?
O5 C14 C13 115.7(3) . . ?
C15 C14 C13 120.7(3) . . ?
N1 C9 C8 177.6(4) . . ?
N3 C21 C20 177.9(4) . . ?
C18 C13 C14 116.0(3) . . ?
C18 C13 C19 125.7(3) . . ?
C14 C13 C19 118.3(3) . . ?
C6 C5 C4 118.3(3) . . ?
C6 C5 H5 120.8 . . ?
C4 C5 H5 120.8 . . ?
C7 C8 C9 123.5(3) . . ?
C7 C8 C10 118.9(3) . . ?
C9 C8 C10 117.5(3) . . ?
C22 N4 H4A 120.0 . . ?
C22 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
O6 C22 N4 122.6(4) . . ?
O6 C22 C20 120.8(3) . . ?
N4 C22 C20 116.6(3) . . ?
C8 C7 C1 132.8(3) . . ?
C8 C7 H7 113.6 . . ?
C1 C7 H7 113.6 . . ?
C5 C6 C1 122.7(3) . . ?
C5 C6 H6 118.6 . . ?
C1 C6 H6 118.6 . . ?
C18 C17 C16 118.0(4) . . ?
C18 C17 H17 121.0 . . ?
C16 C17 H17 121.0 . . ?
O2 C2 C3 122.7(3) . . ?
O2 C2 C1 116.5(3) . . ?
C3 C2 C1 120.8(3) . . ?
O4 C16 C17 124.7(4) . . ?
O4 C16 C15 115.2(3) . . ?
C17 C16 C15 120.2(3) . . ?
C6 C1 C2 117.1(3) . . ?
C6 C1 C7 124.6(3) . . ?
C2 C1 C7 118.3(3) . . ?
C17 C18 C13 124.3(3) . . ?
C17 C18 H18 117.9 . . ?
C13 C18 H18 117.9 . . ?
C20 C19 C13 132.0(3) . . ?
C20 C19 H19 114(2) . . ?
C13 C19 H19 114(2) . . ?
O1 C4 C3 114.6(3) . . ?
O1 C4 C5 124.2(3) . . ?
C3 C4 C5 121.2(4) . . ?
O5 C24 H24A 109.5 . . ?
O5 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O5 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O3 C10 N2 121.7(4) . . ?
O3 C10 C8 120.8(3) . . ?
N2 C10 C8 117.4(3) . . ?
O4 C23 H23A 109.5 . . ?
O4 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O4 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C4 C3 C2 119.8(3) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
O2 C12 H12A 109.5 . . ?
O2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O1 C11 H11A 109.5 . . ?
O1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C14 C15 C16 120.9(3) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?

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
C24 O5 C14 C15 -1.9(6) . . . . ?
C24 O5 C14 C13 178.8(3) . . . . ?
C19 C20 C21 N3 165(13) . . . . ?
C22 C20 C21 N3 -16(13) . . . . ?
O5 C14 C13 C18 -179.9(3) . . . . ?
C15 C14 C13 C18 0.8(5) . . . . ?
O5 C14 C13 C19 -1.0(5) . . . . ?
C15 C14 C13 C19 179.7(3) . . . . ?
N1 C9 C8 C7 -178(100) . . . . ?
N1 C9 C8 C10 1(11) . . . . ?
C19 C20 C22 O6 -0.9(6) . . . . ?
C21 C20 C22 O6 179.5(4) . . . . ?
C19 C20 C22 N4 179.7(4) . . . . ?
C21 C20 C22 N4 0.0(5) . . . . ?
C9 C8 C7 C1 -1.5(7) . . . . ?
C10 C8 C7 C1 -179.9(4) . . . . ?
C4 C5 C6 C1 -0.1(6) . . . . ?
C12 O2 C2 C3 0.8(5) . . . . ?
C12 O2 C2 C1 -179.0(3) . . . . ?
C23 O4 C16 C17 2.2(6) . . . . ?
C23 O4 C16 C15 -178.0(4) . . . . ?
C18 C17 C16 O4 179.8(4) . . . . ?
C18 C17 C16 C15 0.0(6) . . . . ?
C5 C6 C1 C2 -0.4(6) . . . . ?
C5 C6 C1 C7 179.4(4) . . . . ?
O2 C2 C1 C6 -179.7(3) . . . . ?
C3 C2 C1 C6 0.6(5) . . . . ?
O2 C2 C1 C7 0.5(5) . . . . ?
C3 C2 C1 C7 -179.3(3) . . . . ?
C8 C7 C1 C6 -3.0(7) . . . . ?
C8 C7 C1 C2 176.9(4) . . . . ?
C16 C17 C18 C13 0.7(6) . . . . ?
C14 C13 C18 C17 -1.1(6) . . . . ?
C19 C13 C18 C17 -180.0(4) . . . . ?
C21 C20 C19 C13 0.0(7) . . . . ?
C22 C20 C19 C13 -179.6(4) . . . . ?
C18 C13 C19 C20 -2.8(7) . . . . ?
C14 C13 C19 C20 178.4(4) . . . . ?
C11 O1 C4 C3 175.6(4) . . . . ?
C11 O1 C4 C5 -5.1(6) . . . . ?
C6 C5 C4 O1 -178.7(4) . . . . ?
C6 C5 C4 C3 0.6(6) . . . . ?
C7 C8 C10 O3 1.3(6) . . . . ?
C9 C8 C10 O3 -177.3(4) . . . . ?
C7 C8 C10 N2 -178.6(4) . . . . ?
C9 C8 C10 N2 2.9(6) . . . . ?
O1 C4 C3 C2 178.9(3) . . . . ?
C5 C4 C3 C2 -0.4(6) . . . . ?
O2 C2 C3 C4 -179.9(3) . . . . ?
C1 C2 C3 C4 -0.2(6) . . . . ?
O5 C14 C15 C16 -179.4(4) . . . . ?
C13 C14 C15 C16 -0.1(6) . . . . ?
O4 C16 C15 C14 179.9(3) . . . . ?
C17 C16 C15 C14 -0.3(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.840
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.058
####################################################################### 
# 
# 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_skv
_database_code_depnum_ccdc_archive 'CCDC 1486590'
_audit_update_record             
;
2016-06-18 deposited with the CCDC.
2016-08-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         CHNO
_chemical_formula_sum            'C11 H10 N2 O2'
_chemical_formula_weight         202.21

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   'P 1 21/c 1'

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                   3.9225(3)
_cell_length_b                   10.7762(9)
_cell_length_c                   23.142(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.453(7)
_cell_angle_gamma                90.00
_cell_volume                     976.43(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    862
_cell_measurement_theta_min      3.2451
_cell_measurement_theta_max      29.0183

_exptl_crystal_description       rectangular
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             424
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.91656
_exptl_absorpt_correction_T_max  1.00000
_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  'Xcalibur, Eos'
_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            3726
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_av_sigmaI/netI    0.0439
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         3.25
_diffrn_reflns_theta_max         29.08
_reflns_number_total             2119
_reflns_number_gt                1414
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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 > 2σ(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)+(0.0499P)²+0.0475P] 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       0.018(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2119
_refine_ls_number_parameters     138
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0796
_refine_ls_R_factor_gt           0.0466
_refine_ls_wR_factor_ref         0.1223
_refine_ls_wR_factor_gt          0.1021
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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
O2 O 0.0343(3) 0.83921(12) 0.01244(6) 0.0582(4) Uani 1 1 d . . .
O1 O 0.7343(3) 0.17742(11) 0.15441(6) 0.0544(4) Uani 1 1 d . . .
C7 C 0.3341(4) 0.65048(16) 0.07697(7) 0.0398(4) Uani 1 1 d . . .
H7 H 0.2065 0.6422 0.0420 0.048 Uiso 1 1 calc R . .
C6 C 0.6297(4) 0.51557(16) 0.15477(7) 0.0415(4) Uani 1 1 d . . .
H6 H 0.6832 0.5842 0.1779 0.050 Uiso 1 1 calc R . .
C8 C 0.3702(4) 0.76876(16) 0.09441(7) 0.0385(4) Uani 1 1 d . . .
C1 C 0.4520(4) 0.53330(16) 0.10109(7) 0.0365(4) Uani 1 1 d . . .
N2 N 0.2657(4) 0.98486(14) 0.07155(7) 0.0583(5) Uani 1 1 d . . .
H2B H 0.1762 1.0439 0.0508 0.070 Uiso 1 1 calc R . .
H2A H 0.3907 1.0017 0.1024 0.070 Uiso 1 1 calc R . .
C2 C 0.3789(4) 0.42733(17) 0.06799(7) 0.0437(4) Uani 1 1 d . . .
H2 H 0.2587 0.4358 0.0323 0.052 Uiso 1 1 calc R . .
C4 C 0.6516(4) 0.29681(16) 0.13965(7) 0.0392(4) Uani 1 1 d . . .
C3 C 0.4781(5) 0.31158(17) 0.08617(8) 0.0464(5) Uani 1 1 d . . .
H3 H 0.4293 0.2429 0.0627 0.056 Uiso 1 1 calc R . .
N1 N 0.6993(5) 0.84178(17) 0.18777(8) 0.0678(6) Uani 1 1 d . . .
C10 C 0.2112(4) 0.86809(17) 0.05614(8) 0.0418(4) Uani 1 1 d . . .
C5 C 0.7276(4) 0.39958(17) 0.17431(7) 0.0427(4) Uani 1 1 d . . .
H5 H 0.8432 0.3901 0.2103 0.051 Uiso 1 1 calc R . .
C9 C 0.5541(5) 0.80680(16) 0.14650(8) 0.0447(4) Uani 1 1 d . . .
C11 C 0.9129(5) 0.15572(18) 0.20876(9) 0.0571(6) Uani 1 1 d . . .
H11C H 1.1234 0.2014 0.2107 0.086 Uiso 1 1 calc R . .
H11A H 0.9609 0.0687 0.2130 0.086 Uiso 1 1 calc R . .
H11B H 0.7750 0.1824 0.2393 0.086 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 1.2314(19) . ?
O1 C4 1.365(2) . ?
O1 C11 1.422(2) . ?
C7 C8 1.342(2) . ?
C7 C1 1.445(2) . ?
C7 H7 0.9300 . ?
C6 C5 1.376(2) . ?
C6 C1 1.401(2) . ?
C6 H6 0.9300 . ?
C8 C9 1.427(2) . ?
C8 C10 1.501(2) . ?
C1 C2 1.395(2) . ?
N2 C10 1.322(2) . ?
N2 H2B 0.8600 . ?
N2 H2A 0.8600 . ?
C2 C3 1.365(2) . ?
C2 H2 0.9300 . ?
C4 C3 1.385(2) . ?
C4 C5 1.389(2) . ?
C3 H3 0.9300 . ?
N1 C9 1.146(2) . ?
C5 H5 0.9300 . ?
C11 H11C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?

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
C4 O1 C11 118.25(14) . . ?
C8 C7 C1 133.49(16) . . ?
C8 C7 H7 113.3 . . ?
C1 C7 H7 113.3 . . ?
C5 C6 C1 121.97(16) . . ?
C5 C6 H6 119.0 . . ?
C1 C6 H6 119.0 . . ?
C7 C8 C9 124.44(16) . . ?
C7 C8 C10 117.86(15) . . ?
C9 C8 C10 117.68(15) . . ?
C2 C1 C6 116.76(15) . . ?
C2 C1 C7 116.92(15) . . ?
C6 C1 C7 126.32(16) . . ?
C10 N2 H2B 120.0 . . ?
C10 N2 H2A 120.0 . . ?
H2B N2 H2A 120.0 . . ?
C3 C2 C1 122.22(15) . . ?
C3 C2 H2 118.9 . . ?
C1 C2 H2 118.9 . . ?
O1 C4 C3 115.36(16) . . ?
O1 C4 C5 124.57(15) . . ?
C3 C4 C5 120.07(16) . . ?
C2 C3 C4 119.72(17) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
O2 C10 N2 122.42(17) . . ?
O2 C10 C8 119.87(16) . . ?
N2 C10 C8 117.71(15) . . ?
C6 C5 C4 119.25(15) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
N1 C9 C8 177.48(19) . . ?
O1 C11 H11C 109.5 . . ?
O1 C11 H11A 109.5 . . ?
H11C C11 H11A 109.5 . . ?
O1 C11 H11B 109.5 . . ?
H11C C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?

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
C1 C7 C8 C9 0.0(3) . . . . ?
C1 C7 C8 C10 178.97(16) . . . . ?
C5 C6 C1 C2 -0.2(2) . . . . ?
C5 C6 C1 C7 179.14(15) . . . . ?
C8 C7 C1 C2 -176.24(17) . . . . ?
C8 C7 C1 C6 4.4(3) . . . . ?
C6 C1 C2 C3 -0.8(2) . . . . ?
C7 C1 C2 C3 179.80(15) . . . . ?
C11 O1 C4 C3 179.96(15) . . . . ?
C11 O1 C4 C5 -0.5(3) . . . . ?
C1 C2 C3 C4 1.3(3) . . . . ?
O1 C4 C3 C2 178.86(15) . . . . ?
C5 C4 C3 C2 -0.7(3) . . . . ?
C7 C8 C10 O2 5.0(2) . . . . ?
C9 C8 C10 O2 -175.97(17) . . . . ?
C7 C8 C10 N2 -175.72(16) . . . . ?
C9 C8 C10 N2 3.3(2) . . . . ?
C1 C6 C5 C4 0.7(3) . . . . ?
O1 C4 C5 C6 -179.78(16) . . . . ?
C3 C4 C5 C6 -0.2(2) . . . . ?
C7 C8 C9 N1 177(100) . . . . ?
C10 C8 C9 N1 -2(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.807
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.972
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.140
_refine_diff_density_rms         0.035
