# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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. 
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data_A9_2_a
_database_code_depnum_ccdc_archive 'CCDC 1062760'
_audit_update_record             
;
2015-04-30 deposited with the CCDC.	2019-07-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H16 N2 O2'
_chemical_formula_weight         304.34

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.1822(10)
_cell_length_b                   14.0258(18)
_cell_length_c                   15.7770(19)
_cell_angle_alpha                89.987(9)
_cell_angle_beta                 90.007(10)
_cell_angle_gamma                77.128(10)
_cell_volume                     1549.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1710
_cell_measurement_theta_min      2.58
_cell_measurement_theta_max      18.70

_exptl_crystal_description       Rectangular
_exptl_crystal_colour            Brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_F_000             640
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.086
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15885
_diffrn_reflns_av_unetI/netI     0.1522
_diffrn_reflns_av_R_equivalents  0.0935
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.291
_diffrn_reflns_theta_max         24.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.910
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.910
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.910
_reflns_number_total             5122
_reflns_number_gt                2244
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_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-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+1.7445P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.011(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5122
_refine_ls_number_parameters     420
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1952
_refine_ls_R_factor_gt           0.1074
_refine_ls_wR_factor_ref         0.2926
_refine_ls_wR_factor_gt          0.2463
_refine_ls_goodness_of_fit_ref   1.130
_refine_ls_restrained_S_all      1.130
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O001 O 0.1018(6) 0.7823(3) -0.3281(2) 0.0836(13) Uani 1 1 d . . . . .
O002 O 0.3981(6) 0.7179(3) 0.1715(2) 0.0828(13) Uani 1 1 d . . . . .
N003 N 0.2811(7) 0.4448(3) 0.0649(3) 0.0658(13) Uani 1 1 d . . . . .
O1 O 0.1320(7) 1.2361(3) 0.6037(3) 0.0902(14) Uani 1 1 d . . . . .
H1 H 0.0274 1.2330 0.5845 0.135 Uiso 1 1 calc R U . . .
O2 O 0.3720(7) 0.2628(3) 0.1038(2) 0.0908(14) Uani 1 1 d . . . . .
H2 H 0.3509 0.3112 0.0731 0.136 Uiso 1 1 calc R U . . .
N006 N 0.2331(7) 0.5267(3) 0.0114(3) 0.0687(14) Uani 1 1 d . . . . .
N007 N 0.2194(7) 1.0556(3) 0.5646(3) 0.0659(13) Uani 1 1 d . . . . .
N008 N 0.2667(7) 0.9734(3) 0.5117(3) 0.0697(14) Uani 1 1 d . . . . .
C009 C 0.2106(8) 0.5754(4) -0.1344(3) 0.0573(14) Uani 1 1 d . . . . .
C00A C 0.1373(8) 0.7102(4) -0.2676(3) 0.0624(15) Uani 1 1 d . . . . .
C00B C 0.2899(8) 0.9249(4) 0.3651(3) 0.0583(15) Uani 1 1 d . . . . .
C00C C 0.3621(8) 0.7903(4) 0.2317(3) 0.0627(15) Uani 1 1 d . . . . .
C00D C 0.2512(8) 0.5045(4) -0.0673(3) 0.0655(16) Uani 1 1 d . . . . .
H00D H 0.2929 0.4389 -0.0818 0.079 Uiso 1 1 calc R U . . .
C00E C 0.2025(8) 1.0863(4) 0.7965(3) 0.0606(15) Uani 1 1 d . . . . .
C00F C 0.2996(8) 0.4138(4) 0.2972(3) 0.0617(15) Uani 1 1 d . . . . .
C00G C 0.1900(8) 1.1102(4) 0.7091(3) 0.0585(14) Uani 1 1 d . . . . .
C00H C 0.2611(9) 0.9528(4) 0.2816(3) 0.0693(17) Uani 1 1 d . . . . .
H00H H 0.2163 1.0189 0.2697 0.083 Uiso 1 1 calc R U . . .
C00I C 0.2290(8) 1.0345(4) 0.6439(3) 0.0628(15) Uani 1 1 d . . . . .
H00I H 0.2617 0.9692 0.6603 0.075 Uiso 1 1 calc R U . . .
C00J C 0.1429(8) 1.2082(4) 0.6855(4) 0.0690(16) Uani 1 1 d . . . . .
C00K C 0.3572(8) 0.2912(4) 0.1856(4) 0.0679(16) Uani 1 1 d . . . . .
C00L C 0.3094(8) 0.3898(4) 0.2089(3) 0.0576(14) Uani 1 1 d . . . . .
C00M C 0.3740(9) 0.2402(5) 0.3307(4) 0.0787(19) Uani 1 1 d . . . . .
H00M H 0.3940 0.1898 0.3703 0.094 Uiso 1 1 calc R U . . .
C00N C 0.3943(9) 0.7596(4) 0.3149(3) 0.0729(17) Uani 1 1 d . . . . .
H00N H 0.4398 0.6935 0.3264 0.087 Uiso 1 1 calc R U . . .
C00O C 0.2949(9) 0.8882(4) 0.2149(3) 0.0690(17) Uani 1 1 d . . . . .
H00O H 0.2728 0.9103 0.1595 0.083 Uiso 1 1 calc R U . . .
C00P C 0.1126(9) 1.2818(4) 0.7477(4) 0.0818(19) Uani 1 1 d . . . . .
H00P H 0.0829 1.3470 0.7311 0.098 Uiso 1 1 calc R U . . .
C00Q C 0.2395(8) 0.5466(4) -0.2180(3) 0.0695(17) Uani 1 1 d . . . . .
H00Q H 0.2838 0.4804 -0.2298 0.083 Uiso 1 1 calc R U . . .
C00R C 0.2713(8) 0.4655(4) 0.1445(3) 0.0641(16) Uani 1 1 d . . . . .
H00R H 0.2389 0.5307 0.1612 0.077 Uiso 1 1 calc R U . . .
C00S C 0.3299(8) 0.3383(5) 0.3587(4) 0.0703(17) Uani 1 1 d . . . . .
C00T C 0.2498(8) 0.9957(4) 0.4330(3) 0.0657(16) Uani 1 1 d . . . . .
H00T H 0.2093 1.0613 0.4186 0.079 Uiso 1 1 calc R U . . .
C00U C 0.1710(9) 1.1614(5) 0.8588(4) 0.0721(17) Uani 1 1 d . . . . .
C00V C 0.3604(8) 0.8249(4) 0.3808(3) 0.0698(17) Uani 1 1 d . . . . .
H00V H 0.3842 0.8028 0.4362 0.084 Uiso 1 1 calc R U . . .
C00W C 0.1050(9) 0.7404(4) -0.1848(3) 0.0738(18) Uani 1 1 d . . . . .
H00W H 0.0589 0.8065 -0.1732 0.089 Uiso 1 1 calc R U . . .
C00X C 0.1395(9) 0.6751(4) -0.1192(3) 0.0707(17) Uani 1 1 d . . . . .
H00X H 0.1155 0.6972 -0.0639 0.085 Uiso 1 1 calc R U . . .
C00Y C 0.3874(9) 0.2184(4) 0.2475(4) 0.0831(19) Uani 1 1 d . . . . .
H00Y H 0.4177 0.1532 0.2309 0.100 Uiso 1 1 calc R U . . .
C00Z C 0.1343(10) 0.7532(5) -0.4150(3) 0.085(2) Uani 1 1 d . . . . .
H00A H 0.2639 0.7175 -0.4219 0.128 Uiso 1 1 calc R U . . .
H00B H 0.1115 0.8102 -0.4505 0.128 Uiso 1 1 calc R U . . .
H00C H 0.0490 0.7124 -0.4308 0.128 Uiso 1 1 calc R U . . .
C010 C 0.2582(10) 0.5107(5) 0.3279(4) 0.085(2) Uani 1 1 d . . . . .
H010 H 0.2407 0.5619 0.2891 0.101 Uiso 1 1 calc R U . . .
C011 C 0.2055(9) 0.6119(5) -0.2850(3) 0.0706(17) Uani 1 1 d . . . . .
H011 H 0.2280 0.5902 -0.3406 0.085 Uiso 1 1 calc R U . . .
C012 C 0.1256(9) 1.2598(5) 0.8302(4) 0.0800(19) Uani 1 1 d . . . . .
H012 H 0.1044 1.3102 0.8698 0.096 Uiso 1 1 calc R U . . .
C013 C 0.2411(10) 0.9894(5) 0.8286(4) 0.084(2) Uani 1 1 d . . . . .
H013 H 0.2565 0.9380 0.7901 0.101 Uiso 1 1 calc R U . . .
C014 C 0.3658(10) 0.7473(5) 0.0848(3) 0.087(2) Uani 1 1 d . . . . .
H01A H 0.2321 0.7743 0.0761 0.131 Uiso 1 1 calc R U . . .
H01B H 0.4065 0.6915 0.0486 0.131 Uiso 1 1 calc R U . . .
H01C H 0.4370 0.7957 0.0715 0.131 Uiso 1 1 calc R U . . .
C015 C 0.3110(10) 0.3631(6) 0.4463(4) 0.094(2) Uani 1 1 d . . . . .
H015 H 0.3285 0.3137 0.4869 0.112 Uiso 1 1 calc R U . . .
C016 C 0.1885(10) 1.1379(6) 0.9461(4) 0.093(2) Uani 1 1 d . . . . .
H016 H 0.1695 1.1876 0.9863 0.112 Uiso 1 1 calc R U . . .
C017 C 0.2329(12) 1.0427(7) 0.9716(4) 0.113(3) Uani 1 1 d . . . . .
H017 H 0.2475 1.0277 1.0290 0.136 Uiso 1 1 calc R U . . .
C018 C 0.2566(12) 0.9679(6) 0.9121(4) 0.112(3) Uani 1 1 d . . . . .
H018 H 0.2831 0.9030 0.9298 0.135 Uiso 1 1 calc R U . . .
C019 C 0.2431(12) 0.5322(6) 0.4119(4) 0.110(3) Uani 1 1 d . . . . .
H019 H 0.2161 0.5971 0.4297 0.132 Uiso 1 1 calc R U . . .
C01A C 0.2679(12) 0.4577(7) 0.4709(4) 0.110(3) Uani 1 1 d . . . . .
H01D H 0.2548 0.4728 0.5282 0.132 Uiso 1 1 calc R U . . .


_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
O001 C00A 1.372(6) . ?
O001 C00Z 1.436(6) . ?
O002 C00C 1.372(6) . ?
O002 C014 1.433(6) . ?
N003 C00R 1.288(6) . ?
N003 N006 1.405(6) . ?
O1 C00J 1.347(6) . ?
O1 H1 0.8200 . ?
O2 C00K 1.348(6) . ?
O2 H2 0.8200 . ?
N006 C00D 1.280(6) . ?
N007 C00I 1.284(6) . ?
N007 N008 1.403(6) . ?
N008 C00T 1.279(6) . ?
C009 C00Q 1.382(7) . ?
C009 C00X 1.398(7) . ?
C009 C00D 1.438(7) . ?
C00A C00W 1.377(7) . ?
C00A C011 1.384(8) . ?
C00B C00H 1.377(7) . ?
C00B C00V 1.402(7) . ?
C00B C00T 1.445(7) . ?
C00C C00O 1.376(8) . ?
C00C C00N 1.385(7) . ?
C00D H00D 0.9300 . ?
C00E C00G 1.417(7) . ?
C00E C013 1.419(8) . ?
C00E C00U 1.422(7) . ?
C00F C010 1.412(8) . ?
C00F C00S 1.416(7) . ?
C00F C00L 1.431(7) . ?
C00G C00J 1.391(8) . ?
C00G C00I 1.459(7) . ?
C00H C00O 1.375(7) . ?
C00H H00H 0.9300 . ?
C00I H00I 0.9300 . ?
C00J C00P 1.405(8) . ?
C00K C00Y 1.395(8) . ?
C00K C00L 1.397(7) . ?
C00L C00R 1.450(7) . ?
C00M C00Y 1.345(8) . ?
C00M C00S 1.414(8) . ?
C00M H00M 0.9300 . ?
C00N C00V 1.371(7) . ?
C00N H00N 0.9300 . ?
C00O H00O 0.9300 . ?
C00P C012 1.336(8) . ?
C00P H00P 0.9300 . ?
C00Q C011 1.384(8) . ?
C00Q H00Q 0.9300 . ?
C00R H00R 0.9300 . ?
C00S C015 1.424(8) . ?
C00T H00T 0.9300 . ?
C00U C016 1.416(8) . ?
C00U C012 1.419(9) . ?
C00V H00V 0.9300 . ?
C00W C00X 1.367(7) . ?
C00W H00W 0.9300 . ?
C00X H00X 0.9300 . ?
C00Y H00Y 0.9300 . ?
C00Z H00A 0.9600 . ?
C00Z H00B 0.9600 . ?
C00Z H00C 0.9600 . ?
C010 C019 1.359(8) . ?
C010 H010 0.9300 . ?
C011 H011 0.9300 . ?
C012 H012 0.9300 . ?
C013 C018 1.352(8) . ?
C013 H013 0.9300 . ?
C014 H01A 0.9600 . ?
C014 H01B 0.9600 . ?
C014 H01C 0.9600 . ?
C015 C01A 1.351(10) . ?
C015 H015 0.9300 . ?
C016 C017 1.362(10) . ?
C016 H016 0.9300 . ?
C017 C018 1.389(10) . ?
C017 H017 0.9300 . ?
C018 H018 0.9300 . ?
C019 C01A 1.381(10) . ?
C019 H019 0.9300 . ?
C01A H01D 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
C00A O001 C00Z 117.6(5) . . ?
C00C O002 C014 117.2(5) . . ?
C00R N003 N006 114.2(5) . . ?
C00J O1 H1 109.5 . . ?
C00K O2 H2 109.5 . . ?
C00D N006 N003 113.0(5) . . ?
C00I N007 N008 113.6(5) . . ?
C00T N008 N007 112.7(5) . . ?
C00Q C009 C00X 117.0(5) . . ?
C00Q C009 C00D 120.4(5) . . ?
C00X C009 C00D 122.6(5) . . ?
O001 C00A C00W 116.2(5) . . ?
O001 C00A C011 124.2(5) . . ?
C00W C00A C011 119.6(5) . . ?
C00H C00B C00V 116.8(5) . . ?
C00H C00B C00T 121.3(5) . . ?
C00V C00B C00T 121.9(5) . . ?
O002 C00C C00O 124.9(5) . . ?
O002 C00C C00N 115.8(5) . . ?
C00O C00C C00N 119.3(5) . . ?
N006 C00D C009 123.5(5) . . ?
N006 C00D H00D 118.2 . . ?
C009 C00D H00D 118.2 . . ?
C00G C00E C013 124.2(5) . . ?
C00G C00E C00U 120.4(5) . . ?
C013 C00E C00U 115.4(5) . . ?
C010 C00F C00S 116.7(5) . . ?
C010 C00F C00L 123.3(5) . . ?
C00S C00F C00L 120.0(5) . . ?
C00J C00G C00E 118.8(5) . . ?
C00J C00G C00I 119.7(5) . . ?
C00E C00G C00I 121.5(5) . . ?
C00O C00H C00B 123.5(5) . . ?
C00O C00H H00H 118.3 . . ?
C00B C00H H00H 118.3 . . ?
N007 C00I C00G 121.8(5) . . ?
N007 C00I H00I 119.1 . . ?
C00G C00I H00I 119.1 . . ?
O1 C00J C00G 121.9(5) . . ?
O1 C00J C00P 117.8(6) . . ?
C00G C00J C00P 120.2(6) . . ?
O2 C00K C00Y 117.7(6) . . ?
O2 C00K C00L 122.1(5) . . ?
C00Y C00K C00L 120.2(5) . . ?
C00K C00L C00F 118.5(5) . . ?
C00K C00L C00R 120.3(5) . . ?
C00F C00L C00R 121.2(5) . . ?
C00Y C00M C00S 121.0(5) . . ?
C00Y C00M H00M 119.5 . . ?
C00S C00M H00M 119.5 . . ?
C00V C00N C00C 121.2(5) . . ?
C00V C00N H00N 119.4 . . ?
C00C C00N H00N 119.4 . . ?
C00H C00O C00C 118.9(5) . . ?
C00H C00O H00O 120.6 . . ?
C00C C00O H00O 120.6 . . ?
C012 C00P C00J 121.3(6) . . ?
C012 C00P H00P 119.4 . . ?
C00J C00P H00P 119.4 . . ?
C009 C00Q C011 122.8(5) . . ?
C009 C00Q H00Q 118.6 . . ?
C011 C00Q H00Q 118.6 . . ?
N003 C00R C00L 121.7(5) . . ?
N003 C00R H00R 119.1 . . ?
C00L C00R H00R 119.1 . . ?
C00M C00S C00F 118.5(5) . . ?
C00M C00S C015 122.0(6) . . ?
C00F C00S C015 119.5(6) . . ?
N008 C00T C00B 123.9(5) . . ?
N008 C00T H00T 118.0 . . ?
C00B C00T H00T 118.0 . . ?
C016 C00U C012 121.7(6) . . ?
C016 C00U C00E 120.6(6) . . ?
C012 C00U C00E 117.7(5) . . ?
C00N C00V C00B 120.4(5) . . ?
C00N C00V H00V 119.8 . . ?
C00B C00V H00V 119.8 . . ?
C00X C00W C00A 121.2(6) . . ?
C00X C00W H00W 119.4 . . ?
C00A C00W H00W 119.4 . . ?
C00W C00X C009 120.8(5) . . ?
C00W C00X H00X 119.6 . . ?
C009 C00X H00X 119.6 . . ?
C00M C00Y C00K 121.7(6) . . ?
C00M C00Y H00Y 119.1 . . ?
C00K C00Y H00Y 119.1 . . ?
O001 C00Z H00A 109.5 . . ?
O001 C00Z H00B 109.5 . . ?
H00A C00Z H00B 109.5 . . ?
O001 C00Z H00C 109.5 . . ?
H00A C00Z H00C 109.5 . . ?
H00B C00Z H00C 109.5 . . ?
C019 C010 C00F 122.5(6) . . ?
C019 C010 H010 118.7 . . ?
C00F C010 H010 118.7 . . ?
C00A C011 C00Q 118.6(5) . . ?
C00A C011 H011 120.7 . . ?
C00Q C011 H011 120.7 . . ?
C00P C012 C00U 121.5(5) . . ?
C00P C012 H012 119.2 . . ?
C00U C012 H012 119.2 . . ?
C018 C013 C00E 123.4(6) . . ?
C018 C013 H013 118.3 . . ?
C00E C013 H013 118.3 . . ?
O002 C014 H01A 109.5 . . ?
O002 C014 H01B 109.5 . . ?
H01A C014 H01B 109.5 . . ?
O002 C014 H01C 109.5 . . ?
H01A C014 H01C 109.5 . . ?
H01B C014 H01C 109.5 . . ?
C01A C015 C00S 120.4(6) . . ?
C01A C015 H015 119.8 . . ?
C00S C015 H015 119.8 . . ?
C017 C016 C00U 120.3(6) . . ?
C017 C016 H016 119.8 . . ?
C00U C016 H016 119.8 . . ?
C016 C017 C018 120.2(6) . . ?
C016 C017 H017 119.9 . . ?
C018 C017 H017 119.9 . . ?
C013 C018 C017 120.0(7) . . ?
C013 C018 H018 120.0 . . ?
C017 C018 H018 120.0 . . ?
C010 C019 C01A 119.9(7) . . ?
C010 C019 H019 120.0 . . ?
C01A C019 H019 120.0 . . ?
C015 C01A C019 120.9(7) . . ?
C015 C01A H01D 119.5 . . ?
C019 C01A H01D 119.5 . . ?

_refine_diff_density_max         0.325
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.071
####################################################################### 
# 
# 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_NPED_SNND_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1484206'
_audit_update_record             
;
2016-06-09 deposited with the CCDC.	2019-07-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        'NPED SNND'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H16 N3 O4'
_chemical_formula_weight         362.36

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.8682(5)
_cell_length_b                   11.1818(6)
_cell_length_c                   16.0637(8)
_cell_angle_alpha                88.542(3)
_cell_angle_beta                 73.254(2)
_cell_angle_gamma                70.084(3)
_cell_volume                     1751.83(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6389
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      22.03

_exptl_crystal_description       Plate
_exptl_crystal_colour            Off
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_F_000             756
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    0.098
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17563
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_av_R_equivalents  0.0189
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.328
_diffrn_reflns_theta_max         29.098
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.930
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.930
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.930
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             8741
_reflns_number_gt                5603
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_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-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.014(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         8741
_refine_ls_number_parameters     422
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1113
_refine_ls_R_factor_gt           0.0749
_refine_ls_wR_factor_ref         0.2493
_refine_ls_wR_factor_gt          0.2233
_refine_ls_goodness_of_fit_ref   1.575
_refine_ls_restrained_S_all      1.575
_refine_ls_shift/su_max          0.081
_refine_ls_shift/su_mean         0.002

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O001 O 0.40779(12) 0.00208(15) 0.40736(9) 0.0591(4) Uani 1 1 d . . . . .
H001 H 0.4638 -0.0266 0.3596 0.089 Uiso 1 1 calc R U . . .
O002 O 0.58859(14) 0.41920(17) 0.56097(10) 0.0635(4) Uani 1 1 d . . . . .
H002 H 0.5273 0.4852 0.5854 0.095 Uiso 1 1 calc R U . . .
N003 N 0.65374(17) 0.61158(17) 0.48558(10) 0.0523(4) Uani 1 1 d . . . . .
N004 N 0.85694(17) 0.17082(16) 0.73344(11) 0.0528(4) Uani 1 1 d . . . . .
N005 N 0.26303(16) -0.06699(17) 0.54151(10) 0.0507(4) Uani 1 1 d . . . . .
N006 N 0.35340(17) -0.06074(18) 0.69937(10) 0.0544(5) Uani 1 1 d . . . . .
H006 H 0.3756 -0.0012 0.6710 0.065 Uiso 1 1 calc R U . . .
N3 N 0.18422(17) 0.30980(19) 0.23958(12) 0.0631(5) Uani 1 1 d . . . . .
N2 N 0.65068(19) 0.6031(2) 0.30388(11) 0.0683(6) Uani 1 1 d . . . . .
H2 H 0.5948 0.5735 0.3400 0.082 Uiso 1 1 calc R U . . .
C009 C 0.82846(18) 0.26878(18) 0.68237(11) 0.0422(4) Uani 1 1 d . . . . .
C00A C 0.16539(17) 0.09804(18) 0.45900(11) 0.0404(4) Uani 1 1 d . . . . .
C00B C 0.30618(18) -0.04385(19) 0.78881(12) 0.0469(5) Uani 1 1 d . . . . .
C00C C 0.29565(17) 0.08370(18) 0.39657(11) 0.0422(4) Uani 1 1 d . . . . .
C00D C 0.17986(18) 0.24023(18) 0.31075(12) 0.0445(4) Uani 1 1 d . . . . .
C00E C 0.04772(18) 0.18494(18) 0.44414(12) 0.0449(4) Uani 1 1 d . . . . .
H00E H -0.0369 0.1965 0.4847 0.054 Uiso 1 1 calc R U . . .
C00F C 0.77478(17) 0.47409(18) 0.57472(11) 0.0421(4) Uani 1 1 d . . . . .
C00G C 0.29807(18) 0.15695(19) 0.32554(12) 0.0445(4) Uani 1 1 d . . . . .
H00G H 0.3824 0.1499 0.2862 0.053 Uiso 1 1 calc R U . . .
C00H C 0.15700(18) 0.02079(18) 0.52947(11) 0.0434(4) Uani 1 1 d . . . . .
H00H H 0.0715 0.0333 0.5692 0.052 Uiso 1 1 calc R U . . .
C00I C 0.91153(18) 0.34703(19) 0.66228(12) 0.0466(5) Uani 1 1 d . . . . .
H00I H 0.9849 0.3309 0.6849 0.056 Uiso 1 1 calc R U . . .
C00J C 0.75191(18) 0.57718(19) 0.52376(11) 0.0459(4) Uani 1 1 d . . . . .
H00J H 0.8092 0.6248 0.5161 0.055 Uiso 1 1 calc R U . . .
C00K C 0.05185(18) 0.25320(19) 0.37291(12) 0.0477(5) Uani 1 1 d . . . . .
H00K H -0.0291 0.3085 0.3648 0.057 Uiso 1 1 calc R U . . .
C00L C 0.71999(19) 0.2963(2) 0.64606(12) 0.0481(5) Uani 1 1 d . . . . .
H00L H 0.6656 0.2456 0.6579 0.058 Uiso 1 1 calc R U . . .
C00M C 0.68974(18) 0.3963(2) 0.59298(11) 0.0455(5) Uani 1 1 d . . . . .
C00N C 0.88477(18) 0.44393(19) 0.61096(12) 0.0464(5) Uani 1 1 d . . . . .
H00N H 0.9409 0.4929 0.5989 0.056 Uiso 1 1 calc R U . . .
C00O C 0.2286(2) -0.1116(2) 0.83831(13) 0.0586(5) Uani 1 1 d . . . . .
H00O H 0.2087 -0.1721 0.8111 0.070 Uiso 1 1 calc R U . . .
C00P C 0.6828(2) 0.5715(2) 0.21691(14) 0.0583(5) Uani 1 1 d . . . . .
C00Q C 0.0637(2) 0.3744(2) 0.21241(16) 0.0616(6) Uani 1 1 d . . . . .
H00A H 0.0838 0.4343 0.1705 0.074 Uiso 1 1 calc R U . . .
H00B H -0.0098 0.4230 0.2627 0.074 Uiso 1 1 calc R U . . .
C00R C 0.7059(2) 0.6833(2) 0.33743(13) 0.0555(5) Uani 1 1 d . . . . .
H00C H 0.6953 0.7598 0.3061 0.067 Uiso 1 1 calc R U . . .
H00D H 0.8031 0.6390 0.3284 0.067 Uiso 1 1 calc R U . . .
C00S C 0.3673(2) -0.1729(2) 0.65150(13) 0.0574(6) Uani 1 1 d . . . . .
H00F H 0.3671 -0.2402 0.6908 0.069 Uiso 1 1 calc R U . . .
H00M H 0.4554 -0.2004 0.6069 0.069 Uiso 1 1 calc R U . . .
C00T C 0.2562(2) -0.1561(2) 0.60841(12) 0.0541(5) Uani 1 1 d . . . . .
H00P H 0.2671 -0.2379 0.5825 0.065 Uiso 1 1 calc R U . . .
H00Q H 0.1671 -0.1246 0.6520 0.065 Uiso 1 1 calc R U . . .
C00U C 0.3345(2) 0.0451(2) 0.83191(15) 0.0622(6) Uani 1 1 d . . . . .
H00U H 0.3867 0.0911 0.8001 0.075 Uiso 1 1 calc R U . . .
C00V C 0.6348(3) 0.7199(2) 0.43288(14) 0.0621(6) Uani 1 1 d . . . . .
H00R H 0.6693 0.7798 0.4527 0.075 Uiso 1 1 calc R U . . .
H00S H 0.5375 0.7628 0.4414 0.075 Uiso 1 1 calc R U . . .
C00W C 0.9655(2) 0.1474(2) 0.77492(15) 0.0625(6) Uani 1 1 d . . . . .
H00T H 1.0462 0.1539 0.7321 0.075 Uiso 1 1 calc R U . . .
H00V H 0.9889 0.0606 0.7920 0.075 Uiso 1 1 calc R U . . .
C00X C 0.7787(3) 0.6072(2) 0.15459(15) 0.0733(7) Uani 1 1 d . . . . .
H00X H 0.8235 0.6553 0.1718 0.088 Uiso 1 1 calc R U . . .
C00Y C 0.1814(3) -0.0890(3) 0.92785(16) 0.0805(8) Uani 1 1 d . . . . .
H00Y H 0.1286 -0.1338 0.9607 0.097 Uiso 1 1 calc R U . . .
C00Z C 0.7677(3) 0.0970(2) 0.76009(19) 0.0796(8) Uani 1 1 d . . . . .
H00W H 0.8190 0.0153 0.7766 0.096 Uiso 1 1 calc R U . . .
H00$ H 0.7398 0.0805 0.7106 0.096 Uiso 1 1 calc R U . . .
C010 C 0.9316(3) 0.2348(3) 0.85252(16) 0.0836(8) Uani 1 1 d . . . . .
H01A H 0.9089 0.3212 0.8365 0.125 Uiso 1 1 calc R U . . .
H01B H 1.0091 0.2136 0.8745 0.125 Uiso 1 1 calc R U . . .
H01C H 0.8547 0.2262 0.8968 0.125 Uiso 1 1 calc R U . . .
C011 C 0.2113(3) -0.0012(3) 0.96901(17) 0.0917(9) Uani 1 1 d . . . . .
H011 H 0.1803 0.0125 1.0295 0.110 Uiso 1 1 calc R U . . .
C012 C 0.6186(3) 0.4992(3) 0.18881(18) 0.0842(8) Uani 1 1 d . . . . .
H012 H 0.5535 0.4739 0.2293 0.101 Uiso 1 1 calc R U . . .
C013 C 0.2862(3) 0.0654(3) 0.92095(18) 0.0836(8) Uani 1 1 d . . . . .
H013 H 0.3051 0.1260 0.9489 0.100 Uiso 1 1 calc R U . . .
C014 C 0.0149(3) 0.2863(3) 0.17223(19) 0.0813(8) Uani 1 1 d . . . . .
H01D H 0.0853 0.2407 0.1206 0.122 Uiso 1 1 calc R U . . .
H01E H -0.0661 0.3351 0.1571 0.122 Uiso 1 1 calc R U . . .
H01F H -0.0055 0.2266 0.2132 0.122 Uiso 1 1 calc R U . . .
C015 C 0.8086(4) 0.5728(3) 0.0680(2) 0.1138(14) Uani 1 1 d . . . . .
H015 H 0.8730 0.5983 0.0270 0.137 Uiso 1 1 calc R U . . .
C016 C 0.3204(4) 0.3228(4) 0.1860(2) 0.1171(14) Uani 1 1 d . . . . .
H01G H 0.3038 0.4076 0.1656 0.141 Uiso 1 1 calc R U . . .
H01H H 0.3807 0.3107 0.2222 0.141 Uiso 1 1 calc R U . . .
C017 C 0.6421(3) 0.1605(4) 0.8346(2) 0.1179(13) Uani 1 1 d . . . . .
H01I H 0.5954 0.2450 0.8212 0.177 Uiso 1 1 calc R U . . .
H01J H 0.6680 0.1655 0.8863 0.177 Uiso 1 1 calc R U . . .
H01K H 0.5823 0.1118 0.8440 0.177 Uiso 1 1 calc R U . . .
C018 C 0.7458(6) 0.5022(4) 0.0411(2) 0.148(2) Uani 1 1 d . . . . .
H018 H 0.7670 0.4792 -0.0179 0.177 Uiso 1 1 calc R U . . .
C019 C 0.6504(5) 0.4647(3) 0.1017(2) 0.1245(14) Uani 1 1 d . . . . .
H019 H 0.6072 0.4159 0.0835 0.149 Uiso 1 1 calc R U . . .
C01A C 0.3798(5) 0.2352(5) 0.1178(3) 0.1489(17) Uani 1 1 d . . . . .
H01L H 0.3887 0.1520 0.1380 0.223 Uiso 1 1 calc R U . . .
H01M H 0.4689 0.2377 0.0875 0.223 Uiso 1 1 calc R U . . .
H01N H 0.3243 0.2531 0.0789 0.223 Uiso 1 1 calc R U . . .


_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
O001 C00C 1.305(2) . ?
O001 H001 0.8200 . ?
O002 C00M 1.291(2) . ?
O002 H002 0.8200 . ?
N003 C00J 1.322(2) . ?
N003 C00V 1.450(3) . ?
N004 C009 1.356(2) . ?
N004 C00Z 1.447(3) . ?
N004 C00W 1.462(2) . ?
N005 C00H 1.295(2) . ?
N005 C00T 1.450(2) . ?
N006 C00B 1.373(2) . ?
N006 C00S 1.428(3) . ?
N006 H006 0.8600 . ?
N3 C00D 1.365(2) . ?
N3 C00Q 1.448(3) . ?
N3 C016 1.536(4) . ?
N2 C00P 1.363(3) . ?
N2 C00R 1.426(3) . ?
N2 H2 0.8600 . ?
C009 C00L 1.402(2) . ?
C009 C00I 1.429(3) . ?
C00A C00E 1.398(2) . ?
C00A C00H 1.407(3) . ?
C00A C00C 1.439(2) . ?
C00B C00U 1.389(3) . ?
C00B C00O 1.391(3) . ?
C00C C00G 1.387(2) . ?
C00D C00G 1.387(2) . ?
C00D C00K 1.422(3) . ?
C00E C00K 1.358(3) . ?
C00E H00E 0.9300 . ?
C00F C00J 1.391(3) . ?
C00F C00N 1.414(2) . ?
C00F C00M 1.441(3) . ?
C00G H00G 0.9300 . ?
C00H H00H 0.9300 . ?
C00I C00N 1.348(3) . ?
C00I H00I 0.9300 . ?
C00J H00J 0.9300 . ?
C00K H00K 0.9300 . ?
C00L C00M 1.395(3) . ?
C00L H00L 0.9300 . ?
C00N H00N 0.9300 . ?
C00O C00Y 1.379(3) . ?
C00O H00O 0.9300 . ?
C00P C00X 1.382(3) . ?
C00P C012 1.389(4) . ?
C00Q C014 1.501(3) . ?
C00Q H00A 0.9700 . ?
C00Q H00B 0.9700 . ?
C00R C00V 1.500(3) . ?
C00R H00C 0.9700 . ?
C00R H00D 0.9700 . ?
C00S C00T 1.514(3) . ?
C00S H00F 0.9700 . ?
C00S H00M 0.9700 . ?
C00T H00P 0.9700 . ?
C00T H00Q 0.9700 . ?
C00U C013 1.370(3) . ?
C00U H00U 0.9300 . ?
C00V H00R 0.9700 . ?
C00V H00S 0.9700 . ?
C00W C010 1.482(3) . ?
C00W H00T 0.9700 . ?
C00W H00V 0.9700 . ?
C00X C015 1.368(4) . ?
C00X H00X 0.9300 . ?
C00Y C011 1.372(4) . ?
C00Y H00Y 0.9300 . ?
C00Z C017 1.497(4) . ?
C00Z H00W 0.9700 . ?
C00Z H00$ 0.9700 . ?
C010 H01A 0.9600 . ?
C010 H01B 0.9600 . ?
C010 H01C 0.9600 . ?
C011 C013 1.355(5) . ?
C011 H011 0.9300 . ?
C012 C019 1.373(4) . ?
C012 H012 0.9300 . ?
C013 H013 0.9300 . ?
C014 H01D 0.9600 . ?
C014 H01E 0.9600 . ?
C014 H01F 0.9600 . ?
C015 C018 1.353(6) . ?
C015 H015 0.9300 . ?
C016 C01A 1.340(5) . ?
C016 H01G 0.9700 . ?
C016 H01H 0.9700 . ?
C017 H01I 0.9600 . ?
C017 H01J 0.9600 . ?
C017 H01K 0.9600 . ?
C018 C019 1.376(6) . ?
C018 H018 0.9300 . ?
C019 H019 0.9300 . ?
C01A H01L 0.9600 . ?
C01A H01M 0.9600 . ?
C01A H01N 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
C00C O001 H001 109.5 . . ?
C00M O002 H002 109.5 . . ?
C00J N003 C00V 121.68(18) . . ?
C009 N004 C00Z 120.99(16) . . ?
C009 N004 C00W 121.80(17) . . ?
C00Z N004 C00W 116.56(17) . . ?
C00H N005 C00T 124.16(16) . . ?
C00B N006 C00S 122.84(18) . . ?
C00B N006 H006 118.6 . . ?
C00S N006 H006 118.6 . . ?
C00D N3 C00Q 122.40(17) . . ?
C00D N3 C016 119.77(17) . . ?
C00Q N3 C016 117.83(18) . . ?
C00P N2 C00R 122.72(18) . . ?
C00P N2 H2 118.6 . . ?
C00R N2 H2 118.6 . . ?
N004 C009 C00L 122.33(17) . . ?
N004 C009 C00I 120.27(16) . . ?
C00L C009 C00I 117.38(17) . . ?
C00E C00A C00H 121.38(16) . . ?
C00E C00A C00C 117.85(16) . . ?
C00H C00A C00C 120.64(16) . . ?
N006 C00B C00U 119.35(19) . . ?
N006 C00B C00O 122.26(19) . . ?
C00U C00B C00O 118.38(19) . . ?
O001 C00C C00G 121.68(16) . . ?
O001 C00C C00A 119.75(15) . . ?
C00G C00C C00A 118.57(16) . . ?
N3 C00D C00G 121.82(17) . . ?
N3 C00D C00K 120.09(16) . . ?
C00G C00D C00K 118.09(16) . . ?
C00K C00E C00A 122.71(17) . . ?
C00K C00E H00E 118.6 . . ?
C00A C00E H00E 118.6 . . ?
C00J C00F C00N 119.36(17) . . ?
C00J C00F C00M 122.57(16) . . ?
C00N C00F C00M 118.07(16) . . ?
C00C C00G C00D 122.68(17) . . ?
C00C C00G H00G 118.7 . . ?
C00D C00G H00G 118.7 . . ?
N005 C00H C00A 122.96(16) . . ?
N005 C00H H00H 118.5 . . ?
C00A C00H H00H 118.5 . . ?
C00N C00I C009 120.72(16) . . ?
C00N C00I H00I 119.6 . . ?
C009 C00I H00I 119.6 . . ?
N003 C00J C00F 124.02(18) . . ?
N003 C00J H00J 118.0 . . ?
C00F C00J H00J 118.0 . . ?
C00E C00K C00D 120.05(16) . . ?
C00E C00K H00K 120.0 . . ?
C00D C00K H00K 120.0 . . ?
C00M C00L C009 123.08(18) . . ?
C00M C00L H00L 118.5 . . ?
C009 C00L H00L 118.5 . . ?
O002 C00M C00L 121.38(17) . . ?
O002 C00M C00F 120.53(17) . . ?
C00L C00M C00F 118.09(15) . . ?
C00I C00N C00F 122.66(17) . . ?
C00I C00N H00N 118.7 . . ?
C00F C00N H00N 118.7 . . ?
C00Y C00O C00B 119.9(2) . . ?
C00Y C00O H00O 120.1 . . ?
C00B C00O H00O 120.1 . . ?
N2 C00P C00X 122.7(2) . . ?
N2 C00P C012 119.4(2) . . ?
C00X C00P C012 117.9(2) . . ?
N3 C00Q C014 113.96(19) . . ?
N3 C00Q H00A 108.8 . . ?
C014 C00Q H00A 108.8 . . ?
N3 C00Q H00B 108.8 . . ?
C014 C00Q H00B 108.8 . . ?
H00A C00Q H00B 107.7 . . ?
N2 C00R C00V 110.88(18) . . ?
N2 C00R H00C 109.5 . . ?
C00V C00R H00C 109.5 . . ?
N2 C00R H00D 109.5 . . ?
C00V C00R H00D 109.5 . . ?
H00C C00R H00D 108.1 . . ?
N006 C00S C00T 114.49(17) . . ?
N006 C00S H00F 108.6 . . ?
C00T C00S H00F 108.6 . . ?
N006 C00S H00M 108.6 . . ?
C00T C00S H00M 108.6 . . ?
H00F C00S H00M 107.6 . . ?
N005 C00T C00S 110.60(17) . . ?
N005 C00T H00P 109.5 . . ?
C00S C00T H00P 109.5 . . ?
N005 C00T H00Q 109.5 . . ?
C00S C00T H00Q 109.5 . . ?
H00P C00T H00Q 108.1 . . ?
C013 C00U C00B 120.4(2) . . ?
C013 C00U H00U 119.8 . . ?
C00B C00U H00U 119.8 . . ?
N003 C00V C00R 113.17(17) . . ?
N003 C00V H00R 108.9 . . ?
C00R C00V H00R 108.9 . . ?
N003 C00V H00S 108.9 . . ?
C00R C00V H00S 108.9 . . ?
H00R C00V H00S 107.8 . . ?
N004 C00W C010 115.32(19) . . ?
N004 C00W H00T 108.4 . . ?
C010 C00W H00T 108.4 . . ?
N004 C00W H00V 108.4 . . ?
C010 C00W H00V 108.4 . . ?
H00T C00W H00V 107.5 . . ?
C015 C00X C00P 120.8(3) . . ?
C015 C00X H00X 119.6 . . ?
C00P C00X H00X 119.6 . . ?
C011 C00Y C00O 120.7(3) . . ?
C011 C00Y H00Y 119.7 . . ?
C00O C00Y H00Y 119.7 . . ?
N004 C00Z C017 113.9(2) . . ?
N004 C00Z H00W 108.8 . . ?
C017 C00Z H00W 108.8 . . ?
N004 C00Z H00$ 108.8 . . ?
C017 C00Z H00$ 108.8 . . ?
H00W C00Z H00$ 107.7 . . ?
C00W C010 H01A 109.5 . . ?
C00W C010 H01B 109.5 . . ?
H01A C010 H01B 109.5 . . ?
C00W C010 H01C 109.5 . . ?
H01A C010 H01C 109.5 . . ?
H01B C010 H01C 109.5 . . ?
C013 C011 C00Y 119.6(2) . . ?
C013 C011 H011 120.2 . . ?
C00Y C011 H011 120.2 . . ?
C019 C012 C00P 120.5(3) . . ?
C019 C012 H012 119.7 . . ?
C00P C012 H012 119.7 . . ?
C011 C013 C00U 121.1(3) . . ?
C011 C013 H013 119.5 . . ?
C00U C013 H013 119.5 . . ?
C00Q C014 H01D 109.5 . . ?
C00Q C014 H01E 109.5 . . ?
H01D C014 H01E 109.5 . . ?
C00Q C014 H01F 109.5 . . ?
H01D C014 H01F 109.5 . . ?
H01E C014 H01F 109.5 . . ?
C018 C015 C00X 120.9(4) . . ?
C018 C015 H015 119.6 . . ?
C00X C015 H015 119.6 . . ?
C01A C016 N3 109.4(4) . . ?
C01A C016 H01G 109.8 . . ?
N3 C016 H01G 109.8 . . ?
C01A C016 H01H 109.8 . . ?
N3 C016 H01H 109.8 . . ?
H01G C016 H01H 108.2 . . ?
C00Z C017 H01I 109.5 . . ?
C00Z C017 H01J 109.5 . . ?
H01I C017 H01J 109.5 . . ?
C00Z C017 H01K 109.5 . . ?
H01I C017 H01K 109.5 . . ?
H01J C017 H01K 109.5 . . ?
C015 C018 C019 119.6(3) . . ?
C015 C018 H018 120.2 . . ?
C019 C018 H018 120.2 . . ?
C012 C019 C018 120.3(4) . . ?
C012 C019 H019 119.9 . . ?
C018 C019 H019 119.9 . . ?
C016 C01A H01L 109.5 . . ?
C016 C01A H01M 109.5 . . ?
H01L C01A H01M 109.5 . . ?
C016 C01A H01N 109.5 . . ?
H01L C01A H01N 109.5 . . ?
H01M C01A H01N 109.5 . . ?

_refine_diff_density_max         0.776
_refine_diff_density_min         -0.410
_refine_diff_density_rms         0.092

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1501269'
_audit_update_record             
;
2016-10-20 deposited with the CCDC.	2019-07-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H12 N2 O2'
_chemical_formula_weight         240.26

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   16.524(3)
_cell_length_b                   5.9394(12)
_cell_length_c                   13.232(2)
_cell_angle_alpha                90
_cell_angle_beta                 113.560(11)
_cell_angle_gamma                90
_cell_volume                     1190.3(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_F_000             504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.092
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12164
_diffrn_reflns_av_unetI/netI     0.0551
_diffrn_reflns_av_R_equivalents  0.0971
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.344
_diffrn_reflns_theta_max         20.809
_diffrn_reflns_theta_full        20.809
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1239
_reflns_number_gt                915
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0829P)²+0.3605P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1239
_refine_ls_number_parameters     166
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0828
_refine_ls_R_factor_gt           0.0525
_refine_ls_wR_factor_ref         0.1502
_refine_ls_wR_factor_gt          0.1276
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N2 N 0.5264(3) -0.0501(8) 0.4755(4) 0.0527(15) Uani 1 1 d . . . . .
C13 C 0.5930(4) 0.0067(10) 0.3480(5) 0.0460(16) Uani 1 1 d . . . . .
O1 O 0.8770(4) 0.3859(7) 0.3246(4) 0.0686(15) Uani 1 1 d . . . . .
H1 H 0.9097 0.3274 0.3828 0.103 Uiso 1 1 calc R U . . .
O2 O 0.6231(3) -0.3563(7) 0.4331(4) 0.0725(16) Uani 1 1 d . . . . .
H2 H 0.5962 -0.2989 0.4668 0.109 Uiso 1 1 calc R U . . .
C14 C 0.5417(4) 0.0802(11) 0.4084(5) 0.0482(18) Uani 1 1 d . . . . .
H14 H 0.5193 0.2260 0.3981 0.058 Uiso 1 1 calc R U . . .
C6 C 0.9083(4) 0.0351(11) 0.2560(5) 0.0431(16) Uani 1 1 d . . . . .
N1 N 0.9748(3) 0.0582(8) 0.4519(4) 0.0526(16) Uani 1 1 d . . . . .
C2 C 0.8208(5) 0.3231(11) 0.1331(6) 0.057(2) Uani 1 1 d . . . . .
H2A H 0.7937 0.4635 0.1220 0.069 Uiso 1 1 calc R U . . .
C7 C 0.9591(4) -0.0572(10) 0.3639(5) 0.0477(16) Uani 1 1 d . . . . .
H7 H 0.9810 -0.2030 0.3698 0.057 Uiso 1 1 calc R U . . .
C1 C 0.8695(5) 0.2487(11) 0.2394(5) 0.0453(18) Uani 1 1 d . . . . .
C8 C 0.6321(5) -0.2044(11) 0.3623(6) 0.054(2) Uani 1 1 d . . . . .
C5 C 0.8978(4) -0.0914(10) 0.1642(5) 0.0540(17) Uani 1 1 d . . . . .
H5 H 0.9238 -0.2331 0.1741 0.065 Uiso 1 1 calc R U . . .
C9 C 0.6798(5) -0.2651(12) 0.3018(6) 0.062(2) Uani 1 1 d . . . . .
H9 H 0.7071 -0.4052 0.3129 0.074 Uiso 1 1 calc R U . . .
C12 C 0.6027(4) 0.1504(11) 0.2706(6) 0.0592(19) Uani 1 1 d . . . . .
H12 H 0.5776 0.2931 0.2610 0.071 Uiso 1 1 calc R U . . .
C10 C 0.6873(5) -0.1217(13) 0.2261(6) 0.065(2) Uani 1 1 d . . . . .
H10 H 0.7193 -0.1659 0.1855 0.078 Uiso 1 1 calc R U . . .
C11 C 0.6481(5) 0.0892(13) 0.2081(6) 0.068(2) Uani 1 1 d . . . . .
H11 H 0.6525 0.1860 0.1553 0.081 Uiso 1 1 calc R U . . .
C4 C 0.8503(4) -0.0164(12) 0.0586(6) 0.063(2) Uani 1 1 d . . . . .
H4 H 0.8442 -0.1049 -0.0020 0.076 Uiso 1 1 calc R U . . .
C3 C 0.8122(5) 0.1932(13) 0.0451(6) 0.063(2) Uani 1 1 d . . . . .
H3 H 0.7798 0.2469 -0.0257 0.075 Uiso 1 1 calc R U . . .


_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
N2 C14 1.277(7) . ?
N2 N2 1.409(9) 3_656 ?
C13 C8 1.389(9) . ?
C13 C12 1.392(8) . ?
C13 C14 1.444(8) . ?
O1 C1 1.356(7) . ?
O1 H1 0.8200 . ?
O2 C8 1.350(7) . ?
O2 H2 0.8200 . ?
C14 H14 0.9300 . ?
C6 C5 1.379(8) . ?
C6 C1 1.399(8) . ?
C6 C7 1.444(8) . ?
N1 C7 1.286(7) . ?
N1 N1 1.395(9) 3_756 ?
C2 C3 1.356(8) . ?
C2 C1 1.384(9) . ?
C2 H2A 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.377(9) . ?
C5 C4 1.375(8) . ?
C5 H5 0.9300 . ?
C9 C10 1.357(9) . ?
C9 H9 0.9300 . ?
C12 C11 1.368(9) . ?
C12 H12 0.9300 . ?
C10 C11 1.386(9) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C4 C3 1.374(9) . ?
C4 H4 0.9300 . ?
C3 H3 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
C14 N2 N2 113.3(6) . 3_656 ?
C8 C13 C12 118.0(6) . . ?
C8 C13 C14 122.8(6) . . ?
C12 C13 C14 119.2(6) . . ?
C1 O1 H1 109.5 . . ?
C8 O2 H2 109.5 . . ?
N2 C14 C13 121.7(6) . . ?
N2 C14 H14 119.2 . . ?
C13 C14 H14 119.2 . . ?
C5 C6 C1 117.9(6) . . ?
C5 C6 C7 118.8(6) . . ?
C1 C6 C7 123.3(6) . . ?
C7 N1 N1 113.1(6) . 3_756 ?
C3 C2 C1 120.7(7) . . ?
C3 C2 H2A 119.7 . . ?
C1 C2 H2A 119.7 . . ?
N1 C7 C6 121.3(6) . . ?
N1 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
O1 C1 C2 118.4(6) . . ?
O1 C1 C6 122.0(6) . . ?
C2 C1 C6 119.6(6) . . ?
O2 C8 C9 118.4(6) . . ?
O2 C8 C13 121.6(6) . . ?
C9 C8 C13 120.0(6) . . ?
C4 C5 C6 122.5(6) . . ?
C4 C5 H5 118.7 . . ?
C6 C5 H5 118.7 . . ?
C10 C9 C8 120.5(7) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C11 C12 C13 122.3(6) . . ?
C11 C12 H12 118.8 . . ?
C13 C12 H12 118.8 . . ?
C9 C10 C11 121.3(7) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 H10 119.4 . . ?
C12 C11 C10 117.9(7) . . ?
C12 C11 H11 121.1 . . ?
C10 C11 H11 121.1 . . ?
C3 C4 C5 118.1(7) . . ?
C3 C4 H4 120.9 . . ?
C5 C4 H4 120.9 . . ?
C2 C3 C4 121.2(7) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?

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
N2 N2 C14 C13 -178.6(6) 3_656 . . . ?
C8 C13 C14 N2 -3.0(10) . . . . ?
C12 C13 C14 N2 175.8(6) . . . . ?
N1 N1 C7 C6 -179.7(5) 3_756 . . . ?
C5 C6 C7 N1 176.4(5) . . . . ?
C1 C6 C7 N1 -2.9(9) . . . . ?
C3 C2 C1 O1 179.2(6) . . . . ?
C3 C2 C1 C6 -1.6(10) . . . . ?
C5 C6 C1 O1 -179.3(6) . . . . ?
C7 C6 C1 O1 0.0(9) . . . . ?
C5 C6 C1 C2 1.5(9) . . . . ?
C7 C6 C1 C2 -179.2(6) . . . . ?
C12 C13 C8 O2 -177.7(6) . . . . ?
C14 C13 C8 O2 1.1(11) . . . . ?
C12 C13 C8 C9 0.8(11) . . . . ?
C14 C13 C8 C9 179.6(7) . . . . ?
C1 C6 C5 C4 -0.8(9) . . . . ?
C7 C6 C5 C4 179.9(5) . . . . ?
O2 C8 C9 C10 177.0(6) . . . . ?
C13 C8 C9 C10 -1.6(12) . . . . ?
C8 C13 C12 C11 0.9(11) . . . . ?
C14 C13 C12 C11 -178.0(6) . . . . ?
C8 C9 C10 C11 0.6(12) . . . . ?
C13 C12 C11 C10 -1.8(11) . . . . ?
C9 C10 C11 C12 1.1(11) . . . . ?
C6 C5 C4 C3 0.0(9) . . . . ?
C1 C2 C3 C4 0.8(11) . . . . ?
C5 C4 C3 C2 0.0(10) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 N2 0.82 1.91 2.626(6) 145.9 .

_refine_diff_density_max         0.160
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.044

