# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1875864'
_audit_update_record             
;
2018-10-29 deposited with the CCDC.
2018-11-27 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H7 N O2, C7 H7 N O2'
_chemical_formula_sum            'C14 H14 N2 O4'
_chemical_formula_weight         274.27

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 n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'

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

_cell_length_a                   26.744(2)
_cell_length_b                   3.8660(3)
_cell_length_c                   24.352(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2517.8(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6367
_cell_measurement_theta_min      2.261
_cell_measurement_theta_max      30.303

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1152
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9684
_exptl_absorpt_correction_T_max  0.9946
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(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 SMART APEX II'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         .
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        0
_diffrn_reflns_number            23730
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_sigmaI/netI    0.0201
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         1.52
_diffrn_reflns_theta_max         28.00
_reflns_number_total             3090
_reflns_number_gt                2818
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'

_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)+(0.0639P)²+0.4202P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3090
_refine_ls_number_parameters     401
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0353
_refine_ls_wR_factor_ref         0.0937
_refine_ls_wR_factor_gt          0.0898
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_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
N1 N 0.32905(8) 0.6029(6) 0.45928(9) 0.0232(4) Uani 1 1 d . . .
H10 H 0.3542(12) 0.499(8) 0.4499(13) 0.028 Uiso 1 1 d . . .
H11 H 0.3211(11) 0.617(8) 0.4934(14) 0.028 Uiso 1 1 d . . .
O11 O 0.31180(6) 0.6319(5) 0.36925(7) 0.0285(4) Uani 1 1 d . . .
O12 O 0.22760(7) 0.8615(5) 0.33311(7) 0.0277(4) Uani 1 1 d . . .
H1 H 0.2580(15) 0.762(10) 0.3328(19) 0.055(11) Uiso 1 1 d . . .
C11 C 0.25126(8) 0.8704(6) 0.42958(9) 0.0176(4) Uani 1 1 d . . .
C12 C 0.21855(8) 0.9469(6) 0.38596(9) 0.0189(4) Uani 1 1 d . . .
C13 C 0.17347(8) 1.1185(6) 0.39627(10) 0.0207(4) Uani 1 1 d . . .
H13 H 0.1518 1.1753 0.3667 0.025 Uiso 1 1 calc R . .
C14 C 0.16043(8) 1.2053(6) 0.44929(11) 0.0210(5) Uani 1 1 d . . .
H14 H 0.1297 1.3207 0.4561 0.025 Uiso 1 1 calc R . .
C15 C 0.19196(9) 1.1254(6) 0.49293(10) 0.0226(5) Uani 1 1 d . . .
H15 H 0.1825 1.1825 0.5294 0.027 Uiso 1 1 calc R . .
C16 C 0.23697(8) 0.9633(6) 0.48320(9) 0.0201(4) Uani 1 1 d . . .
H16 H 0.2587 0.9136 0.5131 0.024 Uiso 1 1 calc R . .
C17 C 0.29925(8) 0.6931(6) 0.41813(10) 0.0198(4) Uani 1 1 d . . .
N2 N 0.61952(8) -0.0703(6) 0.28109(9) 0.0273(4) Uani 1 1 d . . .
H20 H 0.6268(11) -0.016(8) 0.2468(15) 0.033 Uiso 1 1 d . . .
H21 H 0.6402(12) -0.188(8) 0.3008(14) 0.033 Uiso 1 1 d . . .
O21 O 0.39718(6) 0.3965(5) 0.33147(7) 0.0270(4) Uani 1 1 d . . .
H2 H 0.3674(14) 0.470(10) 0.3473(17) 0.054(11) Uiso 1 1 d . . .
O22 O 0.41971(6) 0.2437(5) 0.41668(8) 0.0258(4) Uani 1 1 d . . .
C21 C 0.47827(8) 0.1742(6) 0.34363(9) 0.0177(4) Uani 1 1 d . . .
C22 C 0.49091(8) 0.2586(6) 0.28920(11) 0.0197(5) Uani 1 1 d . . .
H22 H 0.4671 0.3716 0.2664 0.024 Uiso 1 1 calc R . .
C23 C 0.53777(8) 0.1782(6) 0.26853(10) 0.0198(4) Uani 1 1 d . . .
H23 H 0.5460 0.2400 0.2319 0.024 Uiso 1 1 calc R . .
C24 C 0.57315(8) 0.0064(6) 0.30120(9) 0.0186(4) Uani 1 1 d . . .
C25 C 0.56011(8) -0.0808(6) 0.35555(9) 0.0195(4) Uani 1 1 d . . .
H25 H 0.5836 -0.1978 0.3782 0.023 Uiso 1 1 calc R . .
C26 C 0.51353(8) 0.0025(6) 0.37608(9) 0.0184(4) Uani 1 1 d . . .
H26 H 0.5053 -0.0577 0.4128 0.022 Uiso 1 1 calc R . .
C27 C 0.42987(8) 0.2706(6) 0.36763(11) 0.0185(5) Uani 1 1 d . . .
N3 N 0.41618(7) 0.0928(6) 0.53775(8) 0.0227(4) Uani 1 1 d . . .
H30 H 0.3857(11) -0.030(7) 0.5457(13) 0.027 Uiso 1 1 d . . .
H31 H 0.4244(11) 0.145(8) 0.5032(13) 0.027 Uiso 1 1 d . . .
O31 O 0.43437(6) 0.0957(5) 0.62799(7) 0.0285(4) Uani 1 1 d . . .
O32 O 0.51730(6) 0.3314(5) 0.66572(7) 0.0259(4) Uani 1 1 d . . .
H3 H 0.4883(13) 0.208(9) 0.6619(16) 0.040(9) Uiso 1 1 d . . .
C31 C 0.49431(8) 0.3549(6) 0.56909(9) 0.0168(4) Uani 1 1 d . . .
C32 C 0.52667(8) 0.4265(6) 0.61330(9) 0.0182(4) Uani 1 1 d . . .
C33 C 0.57166(8) 0.6015(6) 0.60381(10) 0.0203(4) Uani 1 1 d . . .
H33 H 0.5932 0.6541 0.6337 0.024 Uiso 1 1 calc R . .
C34 C 0.58484(9) 0.6975(6) 0.55146(11) 0.0221(5) Uani 1 1 d . . .
H34 H 0.6156 0.8143 0.5454 0.027 Uiso 1 1 calc R . .
C35 C 0.55352(9) 0.6251(6) 0.50718(10) 0.0226(5) Uani 1 1 d . . .
H35 H 0.5630 0.6902 0.4710 0.027 Uiso 1 1 calc R . .
C36 C 0.50865(8) 0.4582(6) 0.51621(9) 0.0190(4) Uani 1 1 d . . .
H36 H 0.4871 0.4125 0.4861 0.023 Uiso 1 1 calc R . .
C37 C 0.44642(8) 0.1749(6) 0.57940(10) 0.0196(4) Uani 1 1 d . . .
N4 N 0.12548(8) -0.5280(7) 0.72205(9) 0.0285(5) Uani 1 1 d . . .
H40 H 0.1197(12) -0.455(9) 0.7567(15) 0.034 Uiso 1 1 d . . .
H41 H 0.1041(12) -0.634(9) 0.7055(14) 0.034 Uiso 1 1 d . . .
O41 O 0.34763(6) -0.0950(5) 0.66469(7) 0.0324(4) Uani 1 1 d . . .
H4 H 0.3766(15) -0.044(11) 0.6474(18) 0.058(12) Uiso 1 1 d . . .
O42 O 0.32489(6) -0.2743(5) 0.58130(7) 0.0251(4) Uani 1 1 d . . .
C41 C 0.26623(8) -0.3138(6) 0.65543(9) 0.0184(4) Uani 1 1 d . . .
C42 C 0.25474(9) -0.2266(6) 0.70989(11) 0.0206(5) Uani 1 1 d . . .
H42 H 0.2794 -0.1182 0.7321 0.025 Uiso 1 1 calc R . .
C43 C 0.20852(8) -0.2955(6) 0.73145(10) 0.0222(5) Uani 1 1 d . . .
H43 H 0.2013 -0.2299 0.7682 0.027 Uiso 1 1 calc R . .
C44 C 0.17156(8) -0.4615(6) 0.70012(10) 0.0196(4) Uani 1 1 d . . .
C45 C 0.18338(8) -0.5545(6) 0.64567(9) 0.0211(5) Uani 1 1 d . . .
H45 H 0.1591 -0.6689 0.6237 0.025 Uiso 1 1 calc R . .
C46 C 0.22973(8) -0.4814(6) 0.62399(9) 0.0194(4) Uani 1 1 d . . .
H46 H 0.2370 -0.5455 0.5872 0.023 Uiso 1 1 calc R . .
C47 C 0.31460(9) -0.2306(6) 0.63024(11) 0.0210(5) Uani 1 1 d . . .


_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
N1 C17 1.327(3) . ?
N1 H10 0.82(3) . ?
N1 H11 0.86(3) . ?
O11 C17 1.259(3) . ?
O12 C12 1.350(3) . ?
O12 H1 0.90(4) . ?
C11 C16 1.407(3) . ?
C11 C12 1.408(3) . ?
C11 C17 1.481(3) . ?
C12 C13 1.399(3) . ?
C13 C14 1.379(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.391(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.378(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
N2 C24 1.366(3) . ?
N2 H20 0.88(4) . ?
N2 H21 0.86(3) . ?
O21 C27 1.333(3) . ?
O21 H2 0.93(4) . ?
O22 C27 1.229(3) . ?
C21 C26 1.398(3) . ?
C21 C22 1.406(3) . ?
C21 C27 1.468(3) . ?
C22 C23 1.386(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.403(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.409(3) . ?
C25 C26 1.381(3) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
N3 C37 1.335(3) . ?
N3 H30 0.96(3) . ?
N3 H31 0.89(3) . ?
O31 C37 1.264(3) . ?
O32 C32 1.352(3) . ?
O32 H3 0.91(3) . ?
C31 C36 1.402(3) . ?
C31 C32 1.409(3) . ?
C31 C37 1.479(3) . ?
C32 C33 1.399(3) . ?
C33 C34 1.374(3) . ?
C33 H33 0.9500 . ?
C34 C35 1.394(4) . ?
C34 H34 0.9500 . ?
C35 C36 1.380(3) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
N4 C44 1.367(3) . ?
N4 H40 0.90(4) . ?
N4 H41 0.81(3) . ?
O41 C47 1.326(3) . ?
O41 H4 0.90(4) . ?
O42 C47 1.235(3) . ?
C41 C46 1.400(3) . ?
C41 C42 1.402(3) . ?
C41 C47 1.467(3) . ?
C42 C43 1.369(3) . ?
C42 H42 0.9500 . ?
C43 C44 1.404(3) . ?
C43 H43 0.9500 . ?
C44 C45 1.410(3) . ?
C45 C46 1.377(3) . ?
C45 H45 0.9500 . ?
C46 H46 0.9500 . ?

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
C17 N1 H10 114(2) . . ?
C17 N1 H11 124(2) . . ?
H10 N1 H11 120(3) . . ?
C12 O12 H1 106(3) . . ?
C16 C11 C12 118.55(19) . . ?
C16 C11 C17 121.9(2) . . ?
C12 C11 C17 119.6(2) . . ?
O12 C12 C13 116.2(2) . . ?
O12 C12 C11 123.8(2) . . ?
C13 C12 C11 120.0(2) . . ?
C14 C13 C12 120.1(2) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C15 120.5(2) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C16 C15 C14 119.9(2) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C11 120.9(2) . . ?
C15 C16 H16 119.6 . . ?
C11 C16 H16 119.6 . . ?
O11 C17 N1 120.3(2) . . ?
O11 C17 C11 119.7(2) . . ?
N1 C17 C11 120.0(2) . . ?
C24 N2 H20 119(2) . . ?
C24 N2 H21 120(2) . . ?
H20 N2 H21 121(3) . . ?
C27 O21 H2 114(2) . . ?
C26 C21 C22 118.7(2) . . ?
C26 C21 C27 119.3(2) . . ?
C22 C21 C27 121.9(2) . . ?
C23 C22 C21 120.5(2) . . ?
C23 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C22 C23 C24 120.7(2) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 H23 119.7 . . ?
N2 C24 C23 120.8(2) . . ?
N2 C24 C25 120.6(2) . . ?
C23 C24 C25 118.6(2) . . ?
C26 C25 C24 120.5(2) . . ?
C26 C25 H25 119.8 . . ?
C24 C25 H25 119.8 . . ?
C25 C26 C21 121.0(2) . . ?
C25 C26 H26 119.5 . . ?
C21 C26 H26 119.5 . . ?
O22 C27 O21 121.9(2) . . ?
O22 C27 C21 124.1(2) . . ?
O21 C27 C21 114.1(2) . . ?
C37 N3 H30 118.5(19) . . ?
C37 N3 H31 121(2) . . ?
H30 N3 H31 121(3) . . ?
C32 O32 H3 102(2) . . ?
C36 C31 C32 118.56(19) . . ?
C36 C31 C37 121.8(2) . . ?
C32 C31 C37 119.6(2) . . ?
O32 C32 C33 116.54(19) . . ?
O32 C32 C31 123.66(19) . . ?
C33 C32 C31 119.8(2) . . ?
C34 C33 C32 120.3(2) . . ?
C34 C33 H33 119.8 . . ?
C32 C33 H33 119.8 . . ?
C33 C34 C35 120.6(2) . . ?
C33 C34 H34 119.7 . . ?
C35 C34 H34 119.7 . . ?
C36 C35 C34 119.6(2) . . ?
C36 C35 H35 120.2 . . ?
C34 C35 H35 120.2 . . ?
C35 C36 C31 121.2(2) . . ?
C35 C36 H36 119.4 . . ?
C31 C36 H36 119.4 . . ?
O31 C37 N3 119.9(2) . . ?
O31 C37 C31 119.6(2) . . ?
N3 C37 C31 120.5(2) . . ?
C44 N4 H40 117(2) . . ?
C44 N4 H41 123(2) . . ?
H40 N4 H41 120(3) . . ?
C47 O41 H4 111(3) . . ?
C46 C41 C42 118.4(2) . . ?
C46 C41 C47 119.2(2) . . ?
C42 C41 C47 122.4(2) . . ?
C43 C42 C41 120.9(2) . . ?
C43 C42 H42 119.5 . . ?
C41 C42 H42 119.5 . . ?
C42 C43 C44 121.1(2) . . ?
C42 C43 H43 119.5 . . ?
C44 C43 H43 119.5 . . ?
N4 C44 C43 120.5(2) . . ?
N4 C44 C45 121.4(2) . . ?
C43 C44 C45 118.0(2) . . ?
C46 C45 C44 120.7(2) . . ?
C46 C45 H45 119.7 . . ?
C44 C45 H45 119.7 . . ?
C45 C46 C41 120.9(2) . . ?
C45 C46 H46 119.6 . . ?
C41 C46 H46 119.6 . . ?
O42 C47 O41 121.1(2) . . ?
O42 C47 C41 124.8(2) . . ?
O41 C47 C41 114.2(2) . . ?

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
C16 C11 C12 O12 -178.1(2) . . . . ?
C17 C11 C12 O12 1.4(3) . . . . ?
C16 C11 C12 C13 1.4(3) . . . . ?
C17 C11 C12 C13 -179.1(2) . . . . ?
O12 C12 C13 C14 177.9(2) . . . . ?
C11 C12 C13 C14 -1.6(3) . . . . ?
C12 C13 C14 C15 0.4(4) . . . . ?
C13 C14 C15 C16 1.1(4) . . . . ?
C14 C15 C16 C11 -1.3(4) . . . . ?
C12 C11 C16 C15 0.1(3) . . . . ?
C17 C11 C16 C15 -179.4(2) . . . . ?
C16 C11 C17 O11 -176.1(2) . . . . ?
C12 C11 C17 O11 4.5(3) . . . . ?
C16 C11 C17 N1 3.2(3) . . . . ?
C12 C11 C17 N1 -176.3(2) . . . . ?
C26 C21 C22 C23 -1.1(3) . . . . ?
C27 C21 C22 C23 177.0(2) . . . . ?
C21 C22 C23 C24 1.0(4) . . . . ?
C22 C23 C24 N2 -179.4(2) . . . . ?
C22 C23 C24 C25 -0.4(3) . . . . ?
N2 C24 C25 C26 178.8(2) . . . . ?
C23 C24 C25 C26 -0.2(3) . . . . ?
C24 C25 C26 C21 0.1(3) . . . . ?
C22 C21 C26 C25 0.6(3) . . . . ?
C27 C21 C26 C25 -177.6(2) . . . . ?
C26 C21 C27 O22 8.1(4) . . . . ?
C22 C21 C27 O22 -170.0(2) . . . . ?
C26 C21 C27 O21 -172.7(2) . . . . ?
C22 C21 C27 O21 9.2(3) . . . . ?
C36 C31 C32 O32 -178.3(2) . . . . ?
C37 C31 C32 O32 1.8(3) . . . . ?
C36 C31 C32 C33 0.9(3) . . . . ?
C37 C31 C32 C33 -179.0(2) . . . . ?
O32 C32 C33 C34 177.9(2) . . . . ?
C31 C32 C33 C34 -1.3(3) . . . . ?
C32 C33 C34 C35 0.6(3) . . . . ?
C33 C34 C35 C36 0.6(4) . . . . ?
C34 C35 C36 C31 -1.0(3) . . . . ?
C32 C31 C36 C35 0.3(3) . . . . ?
C37 C31 C36 C35 -179.8(2) . . . . ?
C36 C31 C37 O31 -177.9(2) . . . . ?
C32 C31 C37 O31 2.0(3) . . . . ?
C36 C31 C37 N3 2.7(3) . . . . ?
C32 C31 C37 N3 -177.4(2) . . . . ?
C46 C41 C42 C43 -1.6(4) . . . . ?
C47 C41 C42 C43 177.3(2) . . . . ?
C41 C42 C43 C44 1.3(4) . . . . ?
C42 C43 C44 N4 -179.8(2) . . . . ?
C42 C43 C44 C45 -0.2(3) . . . . ?
N4 C44 C45 C46 179.1(2) . . . . ?
C43 C44 C45 C46 -0.5(3) . . . . ?
C44 C45 C46 C41 0.1(3) . . . . ?
C42 C41 C46 C45 0.9(3) . . . . ?
C47 C41 C46 C45 -178.1(2) . . . . ?
C46 C41 C47 O42 5.6(4) . . . . ?
C42 C41 C47 O42 -173.3(2) . . . . ?
C46 C41 C47 O41 -175.4(2) . . . . ?
C42 C41 C47 O41 5.7(3) . . . . ?

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
O12 H1 O11 0.90(4) 1.76(4) 2.576(2) 149(4) .
N1 H10 O22 0.82(3) 2.17(3) 2.980(3) 174(3) .
N1 H11 O42 0.86(3) 2.18(3) 3.011(3) 162(3) 1_565
O21 H2 O11 0.93(4) 1.70(4) 2.624(2) 173(4) .
N2 H20 O41 0.88(4) 2.16(4) 3.035(3) 174(3) 2_654
N2 H21 O12 0.86(3) 2.55(3) 3.351(3) 154(3) 3
O32 H3 O31 0.91(3) 1.72(4) 2.568(2) 153(3) .
N3 H30 O42 0.96(3) 2.07(3) 3.017(3) 167(3) .
N3 H31 O22 0.89(3) 2.15(3) 3.007(3) 162(3) .
O41 H4 O31 0.90(4) 1.70(4) 2.593(2) 167(4) .
N4 H40 O21 0.90(4) 2.32(4) 3.188(3) 162(3) 4_545
N4 H41 O32 0.81(3) 2.63(3) 3.410(3) 162(3) 3_445

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        28.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.044
####################################################################### 
# 
# 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_z
_database_code_depnum_ccdc_archive 'CCDC 1875868'
_audit_update_record             
;
2018-10-29 deposited with the CCDC.
2018-11-27 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H12 N O, C7 H6 N O2'
_chemical_formula_sum            'C15 H18 N2 O3'
_chemical_formula_weight         274.31

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 n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'

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

_cell_length_a                   12.8319(9)
_cell_length_b                   11.6670(8)
_cell_length_c                   9.5936(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1436.26(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5303
_cell_measurement_theta_min      2.359
_cell_measurement_theta_max      28.924

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             584
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9652
_exptl_absorpt_correction_T_max  0.9737
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(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 SMART APEX II'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         .
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        0
_diffrn_reflns_number            15467
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_sigmaI/netI    0.0167
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.36
_diffrn_reflns_theta_max         29.00
_reflns_number_total             2019
_reflns_number_gt                1892
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'

_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)+(0.0571P)²+0.1719P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2019
_refine_ls_number_parameters     253
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0329
_refine_ls_wR_factor_ref         0.0886
_refine_ls_wR_factor_gt          0.0862
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.047
_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
N1 N 0.41246(10) 0.61688(12) 0.29008(16) 0.0230(3) Uani 1 1 d . . .
H1 H 0.3433(18) 0.596(2) 0.273(3) 0.033(6) Uiso 1 1 d . . .
O1 O 0.61220(10) 0.50533(12) 0.51165(16) 0.0337(3) Uani 1 1 d . . .
H2 H 0.669(2) 0.544(2) 0.552(3) 0.052(8) Uiso 1 1 d . . .
C1 C 0.46070(12) 0.54955(13) 0.38387(18) 0.0229(3) Uani 1 1 d . . .
C2 C 0.56451(12) 0.57380(14) 0.41933(18) 0.0237(3) Uani 1 1 d . . .
C3 C 0.61206(12) 0.66821(15) 0.35612(19) 0.0263(3) Uani 1 1 d . . .
C4 C 0.55864(13) 0.73389(15) 0.2602(2) 0.0271(4) Uani 1 1 d . . .
C5 C 0.45629(12) 0.70764(14) 0.22639(19) 0.0246(3) Uani 1 1 d . . .
C6 C 0.39255(15) 0.77377(17) 0.1239(2) 0.0350(4) Uani 1 1 d . . .
C7 C 0.39757(14) 0.45761(16) 0.4529(2) 0.0312(4) Uani 1 1 d . . .
C8 C 0.32826(19) 0.5088(2) 0.5662(3) 0.0478(6) Uani 1 1 d . . .
H3 H 0.6809(19) 0.6831(19) 0.381(3) 0.038(6) Uiso 1 1 d . . .
H4 H 0.5915(16) 0.797(2) 0.225(3) 0.029(5) Uiso 1 1 d . . .
H61 H 0.420(2) 0.768(3) 0.026(4) 0.092(12) Uiso 1 1 d D . .
H62 H 0.393(2) 0.853(3) 0.144(4) 0.081(11) Uiso 1 1 d D . .
H63 H 0.322(2) 0.748(2) 0.117(3) 0.043(7) Uiso 1 1 d D . .
H71 H 0.4450(19) 0.404(2) 0.496(3) 0.035(6) Uiso 1 1 d . . .
H72 H 0.3534(19) 0.423(2) 0.388(3) 0.036(6) Uiso 1 1 d . . .
H81 H 0.368(2) 0.549(2) 0.630(4) 0.060(9) Uiso 1 1 d D . .
H82 H 0.288(2) 0.449(2) 0.603(3) 0.062(9) Uiso 1 1 d D . .
H83 H 0.278(2) 0.566(2) 0.522(3) 0.058(8) Uiso 1 1 d D . .
N2 N -0.22675(12) 0.31581(15) 0.3409(2) 0.0350(4) Uani 1 1 d . . .
H21 H -0.2646(19) 0.366(2) 0.380(3) 0.035(6) Uiso 1 1 d . . .
H22 H -0.258(2) 0.262(2) 0.281(3) 0.053(8) Uiso 1 1 d . . .
O11 O 0.23751(9) 0.39554(10) 0.12672(15) 0.0289(3) Uani 1 1 d . . .
O12 O 0.21440(8) 0.55791(10) 0.24611(16) 0.0273(3) Uani 1 1 d . . .
C11 C 0.18348(11) 0.46199(13) 0.20374(17) 0.0214(3) Uani 1 1 d . . .
C12 C 0.07682(11) 0.42213(13) 0.24309(18) 0.0209(3) Uani 1 1 d . . .
C13 C 0.03214(13) 0.32747(16) 0.17737(19) 0.0282(4) Uani 1 1 d . . .
C14 C -0.06831(13) 0.29303(17) 0.2087(2) 0.0315(4) Uani 1 1 d . . .
C15 C -0.12750(12) 0.35218(15) 0.30808(19) 0.0258(3) Uani 1 1 d . . .
C16 C -0.08233(13) 0.44662(15) 0.3753(2) 0.0264(3) Uani 1 1 d . . .
C17 C 0.01860(12) 0.48022(14) 0.34340(18) 0.0240(3) Uani 1 1 d . . .
H13 H 0.070(2) 0.287(2) 0.106(3) 0.040(7) Uiso 1 1 d . . .
H14 H -0.097(2) 0.225(2) 0.164(3) 0.058(8) Uiso 1 1 d . . .
H16 H -0.122(2) 0.4866(19) 0.441(3) 0.036(6) Uiso 1 1 d . . .
H17 H 0.0486(17) 0.5438(17) 0.393(3) 0.026(5) Uiso 1 1 d . . .


_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
N1 C1 1.345(2) . ?
N1 C5 1.346(2) . ?
N1 H1 0.93(2) . ?
O1 C2 1.341(2) . ?
O1 H2 0.94(3) . ?
C1 C2 1.404(2) . ?
C1 C7 1.498(2) . ?
C2 C3 1.398(2) . ?
C3 C4 1.380(3) . ?
C3 H3 0.93(2) . ?
C4 C5 1.387(2) . ?
C4 H4 0.91(2) . ?
C5 C6 1.493(3) . ?
C6 H61 1.01(3) . ?
C6 H62 0.94(3) . ?
C6 H63 0.95(3) . ?
C7 C8 1.527(3) . ?
C7 H71 0.96(3) . ?
C7 H72 0.94(3) . ?
C8 H81 0.93(3) . ?
C8 H82 0.94(3) . ?
C8 H83 1.02(3) . ?
N2 C15 1.379(2) . ?
N2 H21 0.85(3) . ?
N2 H22 0.94(3) . ?
O11 C11 1.276(2) . ?
O12 C11 1.255(2) . ?
C11 C12 1.4940(19) . ?
C12 C17 1.394(2) . ?
C12 C13 1.395(2) . ?
C13 C14 1.383(2) . ?
C13 H13 0.96(3) . ?
C14 C15 1.401(2) . ?
C14 H14 0.98(3) . ?
C15 C16 1.402(2) . ?
C16 C17 1.387(2) . ?
C16 H16 0.93(3) . ?
C17 H17 0.96(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C5 124.81(14) . . ?
C1 N1 H1 113.9(15) . . ?
C5 N1 H1 121.3(15) . . ?
C2 O1 H2 109.9(18) . . ?
N1 C1 C2 118.76(14) . . ?
N1 C1 C7 117.69(14) . . ?
C2 C1 C7 123.39(15) . . ?
O1 C2 C3 123.85(15) . . ?
O1 C2 C1 118.24(15) . . ?
C3 C2 C1 117.90(15) . . ?
C4 C3 C2 120.68(15) . . ?
C4 C3 H3 122.5(15) . . ?
C2 C3 H3 116.8(15) . . ?
C3 C4 C5 120.25(16) . . ?
C3 C4 H4 117.6(14) . . ?
C5 C4 H4 122.0(14) . . ?
N1 C5 C4 117.60(15) . . ?
N1 C5 C6 118.46(15) . . ?
C4 C5 C6 123.94(16) . . ?
C5 C6 H61 113(2) . . ?
C5 C6 H62 112(2) . . ?
H61 C6 H62 105(2) . . ?
C5 C6 H63 113.7(16) . . ?
H61 C6 H63 104(2) . . ?
H62 C6 H63 109(2) . . ?
C1 C7 C8 110.48(16) . . ?
C1 C7 H71 108.1(15) . . ?
C8 C7 H71 108.2(17) . . ?
C1 C7 H72 110.2(16) . . ?
C8 C7 H72 106.9(15) . . ?
H71 C7 H72 113(2) . . ?
C7 C8 H81 110(2) . . ?
C7 C8 H82 107.7(19) . . ?
H81 C8 H82 115(3) . . ?
C7 C8 H83 109.2(19) . . ?
H81 C8 H83 107.7(19) . . ?
H82 C8 H83 106.6(19) . . ?
C15 N2 H21 114.9(16) . . ?
C15 N2 H22 117.5(17) . . ?
H21 N2 H22 119(2) . . ?
O12 C11 O11 123.89(14) . . ?
O12 C11 C12 119.03(14) . . ?
O11 C11 C12 117.07(14) . . ?
C17 C12 C13 118.47(14) . . ?
C17 C12 C11 120.93(14) . . ?
C13 C12 C11 120.58(14) . . ?
C14 C13 C12 120.98(16) . . ?
C14 C13 H13 118.8(16) . . ?
C12 C13 H13 120.1(16) . . ?
C13 C14 C15 120.67(16) . . ?
C13 C14 H14 119.5(17) . . ?
C15 C14 H14 119.8(17) . . ?
N2 C15 C14 120.30(16) . . ?
N2 C15 C16 121.24(16) . . ?
C14 C15 C16 118.43(14) . . ?
C17 C16 C15 120.42(16) . . ?
C17 C16 H16 121.0(15) . . ?
C15 C16 H16 118.6(15) . . ?
C16 C17 C12 121.02(16) . . ?
C16 C17 H17 118.7(13) . . ?
C12 C17 H17 120.3(13) . . ?

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
C5 N1 C1 C2 -0.2(3) . . . . ?
C5 N1 C1 C7 175.32(17) . . . . ?
N1 C1 C2 O1 -179.22(15) . . . . ?
C7 C1 C2 O1 5.5(3) . . . . ?
N1 C1 C2 C3 0.8(2) . . . . ?
C7 C1 C2 C3 -174.43(17) . . . . ?
O1 C2 C3 C4 178.95(17) . . . . ?
C1 C2 C3 C4 -1.1(3) . . . . ?
C2 C3 C4 C5 0.7(3) . . . . ?
C1 N1 C5 C4 -0.2(3) . . . . ?
C1 N1 C5 C6 179.72(17) . . . . ?
C3 C4 C5 N1 -0.1(3) . . . . ?
C3 C4 C5 C6 -179.99(18) . . . . ?
N1 C1 C7 C8 -77.3(2) . . . . ?
C2 C1 C7 C8 98.0(2) . . . . ?
O12 C11 C12 C17 -10.6(2) . . . . ?
O11 C11 C12 C17 170.12(15) . . . . ?
O12 C11 C12 C13 167.68(16) . . . . ?
O11 C11 C12 C13 -11.6(2) . . . . ?
C17 C12 C13 C14 1.2(3) . . . . ?
C11 C12 C13 C14 -177.11(17) . . . . ?
C12 C13 C14 C15 -0.4(3) . . . . ?
C13 C14 C15 N2 -178.60(18) . . . . ?
C13 C14 C15 C16 -0.3(3) . . . . ?
N2 C15 C16 C17 178.39(17) . . . . ?
C14 C15 C16 C17 0.1(3) . . . . ?
C15 C16 C17 C12 0.8(3) . . . . ?
C13 C12 C17 C16 -1.4(3) . . . . ?
C11 C12 C17 C16 176.90(16) . . . . ?

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
N1 H1 O12 0.93(2) 1.73(2) 2.6666(17) 178(2) .
O1 H2 O11 0.94(3) 1.57(3) 2.5051(17) 177(3) 2_665
N2 H21 O1 0.85(3) 2.60(3) 3.442(2) 176(2) 1_455
N2 H22 O11 0.94(3) 2.36(3) 3.242(2) 156(2) 3_455

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        29.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.037
####################################################################### 
# 
# 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_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1875866'
_audit_update_record             
;
2018-10-29 deposited with the CCDC.
2018-11-27 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H7 N O2, C4 H4 N2 O3'
_chemical_formula_sum            'C11 H11 N3 O5'
_chemical_formula_weight         265.23

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           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

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                   7.6177(5)
_cell_length_b                   6.5936(4)
_cell_length_c                   22.5748(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.516(1)
_cell_angle_gamma                90.00
_cell_volume                     1124.15(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5128
_cell_measurement_theta_min      2.732
_cell_measurement_theta_max      30.463

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.567
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             552
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9513
_exptl_absorpt_correction_T_max  0.9752
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(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 SMART APEX II'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         .
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        0
_diffrn_reflns_number            11346
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_sigmaI/netI    0.0226
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.73
_diffrn_reflns_theta_max         29.00
_reflns_number_total             2970
_reflns_number_gt                2583
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'

_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)+(0.0503P)²+0.4527P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2970
_refine_ls_number_parameters     216
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0369
_refine_ls_wR_factor_ref         0.0999
_refine_ls_wR_factor_gt          0.0955
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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
N11 N 1.11780(14) -0.16680(16) 0.34503(5) 0.0208(2) Uani 1 1 d . . .
O11 O 0.83589(13) 0.65829(14) 0.43774(4) 0.0233(2) Uani 1 1 d . . .
O12 O 0.69879(11) 0.67673(13) 0.34384(4) 0.01988(19) Uani 1 1 d . . .
C11 C 0.79970(15) 0.58850(17) 0.38219(5) 0.0160(2) Uani 1 1 d . . .
C12 C 0.88606(14) 0.39366(17) 0.37271(5) 0.0152(2) Uani 1 1 d . . .
C13 C 0.97809(15) 0.28566(18) 0.42059(5) 0.0172(2) Uani 1 1 d . . .
C14 C 1.05395(15) 0.09983(17) 0.41170(5) 0.0173(2) Uani 1 1 d . . .
C15 C 1.04150(14) 0.01483(17) 0.35398(5) 0.0154(2) Uani 1 1 d . . .
C16 C 0.94951(15) 0.12438(18) 0.30580(5) 0.0163(2) Uani 1 1 d . . .
C17 C 0.87388(14) 0.30978(17) 0.31521(5) 0.0158(2) Uani 1 1 d . . .
H1 H 0.774(3) 0.767(3) 0.4409(8) 0.042(5) Uiso 1 1 d . . .
H11 H 1.179(2) -0.228(3) 0.3755(8) 0.031(4) Uiso 1 1 d . . .
H12 H 1.108(2) -0.218(3) 0.3077(8) 0.038(5) Uiso 1 1 d . . .
H13 H 0.988(2) 0.341(2) 0.4599(7) 0.026(4) Uiso 1 1 d . . .
H14 H 1.118(2) 0.026(2) 0.4449(7) 0.025(4) Uiso 1 1 d . . .
H16 H 0.947(2) 0.068(2) 0.2666(7) 0.025(4) Uiso 1 1 d . . .
H17 H 0.8129(19) 0.385(2) 0.2822(7) 0.018(3) Uiso 1 1 d . . .
N21 N 0.52682(13) 1.05353(15) 0.36784(4) 0.0171(2) Uani 1 1 d . . .
N22 N 0.51230(13) 1.28605(15) 0.44598(4) 0.0167(2) Uani 1 1 d . . .
O21 O 0.65629(11) 0.98824(13) 0.46236(4) 0.01961(19) Uani 1 1 d . . .
O22 O 0.41112(14) 1.12449(15) 0.27318(4) 0.0275(2) Uani 1 1 d . . .
O23 O 0.37383(12) 1.58735(13) 0.43205(4) 0.0221(2) Uani 1 1 d . . .
C21 C 0.57004(14) 1.10158(17) 0.42703(5) 0.0149(2) Uani 1 1 d . . .
C22 C 0.43542(15) 1.17698(18) 0.32512(5) 0.0173(2) Uani 1 1 d . . .
C23 C 0.36826(15) 1.37507(17) 0.34620(5) 0.0162(2) Uani 1 1 d . . .
C24 C 0.41586(15) 1.42635(17) 0.41085(5) 0.0155(2) Uani 1 1 d . . .
H21 H 0.575(2) 0.934(3) 0.3556(7) 0.031(4) Uiso 1 1 d . . .
H22 H 0.545(2) 1.312(3) 0.4849(8) 0.035(5) Uiso 1 1 d . . .
H23 H 0.416(2) 1.484(3) 0.3237(7) 0.031(4) Uiso 1 1 d . . .
H24 H 0.241(2) 1.377(3) 0.3359(7) 0.031(4) Uiso 1 1 d . . .


_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
N11 C15 1.3578(15) . ?
N11 H11 0.876(18) . ?
N11 H12 0.902(19) . ?
O11 C11 1.3303(14) . ?
O11 H1 0.87(2) . ?
O12 C11 1.2267(14) . ?
C11 C12 1.4717(15) . ?
C12 C17 1.4027(15) . ?
C12 C13 1.4031(15) . ?
C13 C14 1.3806(16) . ?
C13 H13 0.952(16) . ?
C14 C15 1.4101(15) . ?
C14 H14 0.971(16) . ?
C15 C16 1.4130(15) . ?
C16 C17 1.3796(16) . ?
C16 H16 0.958(16) . ?
C17 H17 0.961(15) . ?
N21 C21 1.3708(14) . ?
N21 C22 1.3791(15) . ?
N21 H21 0.928(18) . ?
N22 C24 1.3682(14) . ?
N22 C21 1.3802(14) . ?
N22 H22 0.898(18) . ?
O21 C21 1.2203(14) . ?
O22 C22 1.2133(14) . ?
O23 C24 1.2242(14) . ?
C22 C23 1.5026(16) . ?
C23 C24 1.4958(15) . ?
C23 H23 0.977(18) . ?
C23 H24 0.969(17) . ?

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
C15 N11 H11 118.7(12) . . ?
C15 N11 H12 119.0(12) . . ?
H11 N11 H12 122.2(17) . . ?
C11 O11 H1 108.3(12) . . ?
O12 C11 O11 122.32(11) . . ?
O12 C11 C12 124.20(10) . . ?
O11 C11 C12 113.43(10) . . ?
C17 C12 C13 118.59(10) . . ?
C17 C12 C11 120.14(10) . . ?
C13 C12 C11 121.25(10) . . ?
C14 C13 C12 120.99(10) . . ?
C14 C13 H13 119.3(10) . . ?
C12 C13 H13 119.7(10) . . ?
C13 C14 C15 120.55(10) . . ?
C13 C14 H14 120.9(9) . . ?
C15 C14 H14 118.6(9) . . ?
N11 C15 C14 120.64(10) . . ?
N11 C15 C16 121.01(10) . . ?
C14 C15 C16 118.34(10) . . ?
C17 C16 C15 120.63(10) . . ?
C17 C16 H16 121.7(10) . . ?
C15 C16 H16 117.6(10) . . ?
C16 C17 C12 120.89(10) . . ?
C16 C17 H17 120.4(9) . . ?
C12 C17 H17 118.8(9) . . ?
C21 N21 C22 125.46(10) . . ?
C21 N21 H21 115.6(10) . . ?
C22 N21 H21 118.5(10) . . ?
C24 N22 C21 125.80(10) . . ?
C24 N22 H22 120.0(11) . . ?
C21 N22 H22 114.2(11) . . ?
O21 C21 N21 122.38(10) . . ?
O21 C21 N22 120.22(10) . . ?
N21 C21 N22 117.39(10) . . ?
O22 C22 N21 120.44(11) . . ?
O22 C22 C23 122.60(11) . . ?
N21 C22 C23 116.96(9) . . ?
C24 C23 C22 117.15(9) . . ?
C24 C23 H23 106.4(10) . . ?
C22 C23 H23 108.0(10) . . ?
C24 C23 H24 109.8(10) . . ?
C22 C23 H24 107.7(10) . . ?
H23 C23 H24 107.4(14) . . ?
O23 C24 N22 120.51(10) . . ?
O23 C24 C23 122.35(10) . . ?
N22 C24 C23 117.13(10) . . ?

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
O12 C11 C12 C17 8.31(17) . . . . ?
O11 C11 C12 C17 -174.17(10) . . . . ?
O12 C11 C12 C13 -170.14(11) . . . . ?
O11 C11 C12 C13 7.38(15) . . . . ?
C17 C12 C13 C14 -0.60(17) . . . . ?
C11 C12 C13 C14 177.88(11) . . . . ?
C12 C13 C14 C15 0.43(18) . . . . ?
C13 C14 C15 N11 179.21(11) . . . . ?
C13 C14 C15 C16 -0.11(17) . . . . ?
N11 C15 C16 C17 -179.35(11) . . . . ?
C14 C15 C16 C17 -0.03(16) . . . . ?
C15 C16 C17 C12 -0.15(17) . . . . ?
C13 C12 C17 C16 0.46(17) . . . . ?
C11 C12 C17 C16 -178.03(10) . . . . ?
C22 N21 C21 O21 -177.57(11) . . . . ?
C22 N21 C21 N22 2.30(17) . . . . ?
C24 N22 C21 O21 179.65(11) . . . . ?
C24 N22 C21 N21 -0.23(17) . . . . ?
C21 N21 C22 O22 176.37(11) . . . . ?
C21 N21 C22 C23 -3.99(17) . . . . ?
O22 C22 C23 C24 -176.75(11) . . . . ?
N21 C22 C23 C24 3.62(15) . . . . ?
C21 N22 C24 O23 -178.76(11) . . . . ?
C21 N22 C24 C23 0.19(17) . . . . ?
C22 C23 C24 O23 177.05(11) . . . . ?
C22 C23 C24 N22 -1.88(15) . . . . ?

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
O11 H1 O21 0.87(2) 1.81(2) 2.6669(12) 169.2(18) .
N21 H21 O12 0.928(18) 1.974(18) 2.8928(13) 170.1(15) .
N22 H22 O23 0.898(18) 2.009(18) 2.8993(13) 171.1(16) 3_686
N11 H11 O23 0.876(18) 2.197(18) 3.0477(13) 163.7(16) 1_635
N11 H12 O22 0.902(19) 2.089(19) 2.9850(14) 172.3(17) 2_635

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        29.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.490
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.048
####################################################################### 
# 
# 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_z_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1875865'
_audit_update_record             
;
2018-10-29 deposited with the CCDC.
2018-11-27 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H7 N O2, C7 H7 N O2'
_chemical_formula_sum            'C14 H14 N2 O4'
_chemical_formula_weight         274.27

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 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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                   3.9358(5)
_cell_length_b                   15.944(2)
_cell_length_c                   20.680(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.305(2)
_cell_angle_gamma                90.00
_cell_volume                     1297.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4210
_cell_measurement_theta_min      2.555
_cell_measurement_theta_max      30.526

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             576
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9574
_exptl_absorpt_correction_T_max  0.9948
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(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 SMART APEX II'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         .
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        0
_diffrn_reflns_number            11187
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_sigmaI/netI    0.0236
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         0.98
_diffrn_reflns_theta_max         27.00
_reflns_number_total             2812
_reflns_number_gt                2395
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'

_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)+(0.0430P)²+0.3636P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2812
_refine_ls_number_parameters     238
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0342
_refine_ls_wR_factor_ref         0.0894
_refine_ls_wR_factor_gt          0.0843
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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
N1 N 0.2965(3) 0.44238(7) 0.44532(6) 0.0280(3) Uani 1 1 d . . .
H1 H 0.247(4) 0.4960(12) 0.4393(8) 0.043(5) Uiso 1 1 d . . .
H2 H 0.237(4) 0.4177(11) 0.4812(9) 0.041(5) Uiso 1 1 d . . .
O1 O 0.5411(3) 0.44126(5) 0.34725(4) 0.0283(2) Uani 1 1 d . . .
O2 O 0.6349(3) 0.05191(6) 0.40299(5) 0.0316(2) Uani 1 1 d . . .
H5 H 0.784(6) 0.0372(13) 0.3714(10) 0.062(6) Uiso 1 1 d . . .
C1 C 0.4482(3) 0.40279(8) 0.39681(6) 0.0209(3) Uani 1 1 d . . .
C2 C 0.5018(3) 0.31057(7) 0.40145(6) 0.0188(3) Uani 1 1 d . . .
C3 C 0.3789(3) 0.26133(8) 0.45204(6) 0.0211(3) Uani 1 1 d . . .
C4 C 0.4254(3) 0.17503(8) 0.45203(6) 0.0229(3) Uani 1 1 d . . .
C5 C 0.5975(3) 0.13700(8) 0.40134(6) 0.0225(3) Uani 1 1 d . . .
C6 C 0.7212(3) 0.18530(8) 0.35057(6) 0.0233(3) Uani 1 1 d . . .
C7 C 0.6739(3) 0.27121(8) 0.35108(6) 0.0208(3) Uani 1 1 d . . .
H3 H 0.257(4) 0.2870(9) 0.4863(7) 0.026(4) Uiso 1 1 d . . .
H4 H 0.346(4) 0.1410(10) 0.4863(8) 0.031(4) Uiso 1 1 d . . .
H6 H 0.849(4) 0.1586(9) 0.3147(7) 0.030(4) Uiso 1 1 d . . .
H7 H 0.759(4) 0.3050(9) 0.3168(7) 0.024(4) Uiso 1 1 d . . .
N2 N 1.0732(3) 0.98187(7) 0.31270(6) 0.0281(3) Uani 1 1 d . . .
H21 H 1.059(4) 0.9931(11) 0.2708(9) 0.041(5) Uiso 1 1 d . . .
H22 H 1.268(5) 1.0016(12) 0.3308(9) 0.046(5) Uiso 1 1 d . . .
O11 O 0.9454(3) 0.60730(5) 0.42372(4) 0.0285(2) Uani 1 1 d . . .
O12 O 0.7020(3) 0.59427(6) 0.32609(5) 0.0312(2) Uani 1 1 d . . .
H12 H 0.651(5) 0.5411(13) 0.3398(9) 0.057(6) Uiso 1 1 d . . .
C11 C 0.8584(3) 0.63776(8) 0.37170(6) 0.0217(3) Uani 1 1 d . . .
C12 C 0.9172(3) 0.72690(7) 0.35479(6) 0.0192(3) Uani 1 1 d . . .
C13 C 1.0934(3) 0.77843(8) 0.39817(6) 0.0208(3) Uani 1 1 d . . .
C14 C 1.1458(3) 0.86225(8) 0.38430(6) 0.0226(3) Uani 1 1 d . . .
C15 C 1.0257(3) 0.89570(8) 0.32610(6) 0.0206(3) Uani 1 1 d . . .
C16 C 0.8445(3) 0.84512(8) 0.28314(6) 0.0214(3) Uani 1 1 d . . .
C17 C 0.7923(3) 0.76126(8) 0.29737(6) 0.0204(3) Uani 1 1 d . . .
H13 H 1.189(4) 0.7554(9) 0.4367(7) 0.023(4) Uiso 1 1 d . . .
H14 H 1.272(4) 0.8973(9) 0.4138(7) 0.029(4) Uiso 1 1 d . . .
H16 H 0.754(4) 0.8690(9) 0.2443(7) 0.024(4) Uiso 1 1 d . . .
H17 H 0.665(4) 0.7262(9) 0.2680(7) 0.029(4) Uiso 1 1 d . . .


_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
N1 C1 1.3295(17) . ?
N1 H1 0.885(19) . ?
N1 H2 0.874(19) . ?
O1 C1 1.2506(15) . ?
O2 C5 1.3651(15) . ?
O2 H5 0.91(2) . ?
C1 C2 1.4884(17) . ?
C2 C7 1.3947(17) . ?
C2 C3 1.3965(17) . ?
C3 C4 1.3881(18) . ?
C3 H3 0.951(15) . ?
C4 C5 1.3905(18) . ?
C4 H4 0.948(16) . ?
C5 C6 1.3921(18) . ?
C6 C7 1.3825(17) . ?
C6 H6 0.993(16) . ?
C7 H7 0.953(15) . ?
N2 C15 1.4143(16) . ?
N2 H21 0.886(18) . ?
N2 H22 0.91(2) . ?
O11 C11 1.2274(15) . ?
O12 C11 1.3202(16) . ?
O12 H12 0.92(2) . ?
C11 C12 1.4821(17) . ?
C12 C17 1.3948(17) . ?
C12 C13 1.3980(17) . ?
C13 C14 1.3825(18) . ?
C13 H13 0.954(15) . ?
C14 C15 1.3966(18) . ?
C14 H14 0.964(16) . ?
C15 C16 1.3935(18) . ?
C16 C17 1.3846(17) . ?
C16 H16 0.957(15) . ?
C17 H17 0.964(16) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 H1 116.9(11) . . ?
C1 N1 H2 123.4(11) . . ?
H1 N1 H2 119.6(16) . . ?
C5 O2 H5 107.9(13) . . ?
O1 C1 N1 121.32(12) . . ?
O1 C1 C2 119.69(11) . . ?
N1 C1 C2 118.97(11) . . ?
C7 C2 C3 118.56(11) . . ?
C7 C2 C1 117.75(11) . . ?
C3 C2 C1 123.65(11) . . ?
C4 C3 C2 120.73(12) . . ?
C4 C3 H3 119.6(9) . . ?
C2 C3 H3 119.7(9) . . ?
C3 C4 C5 119.81(12) . . ?
C3 C4 H4 121.6(9) . . ?
C5 C4 H4 118.6(9) . . ?
O2 C5 C4 117.87(11) . . ?
O2 C5 C6 122.05(12) . . ?
C4 C5 C6 120.08(11) . . ?
C7 C6 C5 119.65(12) . . ?
C7 C6 H6 119.9(9) . . ?
C5 C6 H6 120.4(9) . . ?
C6 C7 C2 121.17(11) . . ?
C6 C7 H7 120.4(9) . . ?
C2 C7 H7 118.4(9) . . ?
C15 N2 H21 112.4(11) . . ?
C15 N2 H22 111.6(12) . . ?
H21 N2 H22 112.5(17) . . ?
C11 O12 H12 111.5(12) . . ?
O11 C11 O12 123.03(11) . . ?
O11 C11 C12 122.90(11) . . ?
O12 C11 C12 114.07(11) . . ?
C17 C12 C13 119.14(11) . . ?
C17 C12 C11 121.52(11) . . ?
C13 C12 C11 119.32(11) . . ?
C14 C13 C12 120.60(11) . . ?
C14 C13 H13 119.2(9) . . ?
C12 C13 H13 120.2(9) . . ?
C13 C14 C15 119.84(12) . . ?
C13 C14 H14 120.5(9) . . ?
C15 C14 H14 119.7(9) . . ?
C16 C15 C14 119.89(11) . . ?
C16 C15 N2 120.33(11) . . ?
C14 C15 N2 119.69(12) . . ?
C17 C16 C15 119.95(11) . . ?
C17 C16 H16 120.5(9) . . ?
C15 C16 H16 119.5(9) . . ?
C16 C17 C12 120.55(12) . . ?
C16 C17 H17 120.2(9) . . ?
C12 C17 H17 119.3(9) . . ?

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
O1 C1 C2 C7 3.67(17) . . . . ?
N1 C1 C2 C7 -177.44(12) . . . . ?
O1 C1 C2 C3 -173.89(12) . . . . ?
N1 C1 C2 C3 5.00(18) . . . . ?
C7 C2 C3 C4 -0.34(18) . . . . ?
C1 C2 C3 C4 177.21(12) . . . . ?
C2 C3 C4 C5 0.32(19) . . . . ?
C3 C4 C5 O2 -179.45(12) . . . . ?
C3 C4 C5 C6 -0.37(19) . . . . ?
O2 C5 C6 C7 179.47(11) . . . . ?
C4 C5 C6 C7 0.43(19) . . . . ?
C5 C6 C7 C2 -0.45(19) . . . . ?
C3 C2 C7 C6 0.40(18) . . . . ?
C1 C2 C7 C6 -177.29(11) . . . . ?
O11 C11 C12 C17 -174.98(12) . . . . ?
O12 C11 C12 C17 4.53(17) . . . . ?
O11 C11 C12 C13 3.15(19) . . . . ?
O12 C11 C12 C13 -177.35(11) . . . . ?
C17 C12 C13 C14 -0.48(18) . . . . ?
C11 C12 C13 C14 -178.65(11) . . . . ?
C12 C13 C14 C15 -0.79(19) . . . . ?
C13 C14 C15 C16 1.96(18) . . . . ?
C13 C14 C15 N2 178.60(11) . . . . ?
C14 C15 C16 C17 -1.86(18) . . . . ?
N2 C15 C16 C17 -178.47(11) . . . . ?
C15 C16 C17 C12 0.57(18) . . . . ?
C13 C12 C17 C16 0.59(18) . . . . ?
C11 C12 C17 C16 178.72(11) . . . . ?

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 H5 N2 0.91(2) 1.89(2) 2.7828(16) 167.0(19) 1_545
N1 H1 O11 0.885(19) 2.158(19) 3.0030(15) 159.4(16) 1_455
N1 H2 O11 0.874(19) 2.133(19) 2.9827(15) 163.8(16) 3_666
O12 H12 O1 0.92(2) 1.66(2) 2.5588(13) 167.1(19) .
N2 H22 O2 0.91(2) 2.222(19) 3.0946(17) 161.2(16) 1_665

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.037
####################################################################### 
# 
# 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_z_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1875867'
_audit_update_record             
;
2018-10-29 deposited with the CCDC.
2018-11-27 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H7 N O2, C5 H6 N2 O2'
_chemical_formula_sum            'C12 H13 N3 O4'
_chemical_formula_weight         263.25

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           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'

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

_cell_length_a                   10.1018(5)
_cell_length_b                   11.3577(5)
_cell_length_c                   21.6477(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.4472(7)
_cell_angle_gamma                90.00
_cell_volume                     2456.8(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5520
_cell_measurement_theta_min      2.715
_cell_measurement_theta_max      30.506

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1104
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9577
_exptl_absorpt_correction_T_max  0.9924
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(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 SMART APEX II'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         .
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        0
_diffrn_reflns_number            12630
_diffrn_reflns_av_R_equivalents  0.0203
_diffrn_reflns_av_sigmaI/netI    0.0158
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.72
_diffrn_reflns_theta_max         28.00
_reflns_number_total             2959
_reflns_number_gt                2550
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'

_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)+(0.0452P)²+1.6851P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2959
_refine_ls_number_parameters     224
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0357
_refine_ls_wR_factor_ref         0.0944
_refine_ls_wR_factor_gt          0.0902
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_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
N1 N 0.14748(11) 0.96452(13) 0.29905(6) 0.0386(3) Uani 1 1 d . . .
O1 O 0.65303(9) 0.67403(9) 0.42055(4) 0.0333(2) Uani 1 1 d . . .
O2 O 0.53340(9) 0.66473(8) 0.49991(4) 0.0317(2) Uani 1 1 d . . .
C1 C 0.54436(11) 0.69575(10) 0.44674(5) 0.0242(2) Uani 1 1 d . . .
C2 C 0.44099(11) 0.76230(10) 0.40616(5) 0.0218(2) Uani 1 1 d . . .
C3 C 0.45029(11) 0.78726(11) 0.34362(5) 0.0246(2) Uani 1 1 d . . .
C4 C 0.35266(11) 0.85290(11) 0.30786(5) 0.0257(2) Uani 1 1 d . . .
C5 C 0.24180(11) 0.89604(11) 0.33349(5) 0.0244(2) Uani 1 1 d . . .
C6 C 0.23259(11) 0.86984(11) 0.39621(5) 0.0238(2) Uani 1 1 d . . .
C7 C 0.33075(11) 0.80451(10) 0.43141(5) 0.0226(2) Uani 1 1 d . . .
H1 H 0.1464(16) 0.9698(15) 0.2571(8) 0.043(4) Uiso 1 1 d . . .
H2 H 0.0733(17) 0.9813(14) 0.3153(8) 0.040(4) Uiso 1 1 d . . .
H3 H 0.5250(14) 0.7603(13) 0.3256(6) 0.028(4) Uiso 1 1 d . . .
H4 H 0.3602(14) 0.8696(13) 0.2648(7) 0.029(4) Uiso 1 1 d . . .
H6 H 0.1570(15) 0.8987(13) 0.4137(7) 0.031(4) Uiso 1 1 d . . .
H7 H 0.3256(13) 0.7896(12) 0.4748(6) 0.024(3) Uiso 1 1 d . . .
H10 H 0.7132(19) 0.6364(18) 0.4478(9) 0.057(5) Uiso 1 1 d . . .
N11 N 0.73468(9) 0.53889(9) 0.57778(4) 0.0217(2) Uani 1 1 d . . .
N12 N 0.94052(9) 0.45211(9) 0.57556(4) 0.0215(2) Uani 1 1 d . . .
O11 O 0.84797(8) 0.56933(8) 0.49582(4) 0.02469(19) Uani 1 1 d . . .
O12 O 0.62404(9) 0.51946(8) 0.66064(4) 0.0296(2) Uani 1 1 d . . .
C11 C 0.84156(11) 0.52275(10) 0.54724(5) 0.0202(2) Uani 1 1 d . . .
C12 C 0.72334(11) 0.49459(10) 0.63649(5) 0.0214(2) Uani 1 1 d . . .
C13 C 0.83307(11) 0.42176(10) 0.66379(5) 0.0224(2) Uani 1 1 d . . .
C14 C 0.93747(11) 0.40072(9) 0.63300(5) 0.0206(2) Uani 1 1 d . . .
C15 C 1.05331(12) 0.32245(12) 0.65533(6) 0.0276(3) Uani 1 1 d . . .
H11 H 0.6662(16) 0.5826(14) 0.5569(7) 0.036(4) Uiso 1 1 d . . .
H12 H 1.0093(16) 0.4415(13) 0.5542(7) 0.034(4) Uiso 1 1 d . . .
H13 H 0.8272(14) 0.3852(13) 0.7033(7) 0.029(4) Uiso 1 1 d . . .
H151 H 1.1373(17) 0.3682(15) 0.6628(8) 0.042(4) Uiso 1 1 d . . .
H152 H 1.0613(17) 0.2623(16) 0.6237(8) 0.048(5) Uiso 1 1 d . . .
H153 H 1.0399(16) 0.2829(15) 0.6926(8) 0.039(4) Uiso 1 1 d . . .


_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
N1 C5 1.3637(16) . ?
N1 H1 0.908(18) . ?
N1 H2 0.895(18) . ?
O1 C1 1.3305(14) . ?
O1 H10 0.89(2) . ?
O2 C1 1.2241(14) . ?
C1 C2 1.4711(16) . ?
C2 C7 1.3956(15) . ?
C2 C3 1.3997(15) . ?
C3 C4 1.3797(16) . ?
C3 H3 0.951(15) . ?
C4 C5 1.4088(16) . ?
C4 H4 0.964(15) . ?
C5 C6 1.4064(16) . ?
C6 C7 1.3757(16) . ?
C6 H6 0.958(15) . ?
C7 H7 0.963(14) . ?
N11 C11 1.3587(14) . ?
N11 C12 1.3872(14) . ?
N11 H11 0.915(16) . ?
N12 C11 1.3560(14) . ?
N12 C14 1.3781(14) . ?
N12 H12 0.897(17) . ?
O11 C11 1.2427(13) . ?
O12 C12 1.2303(14) . ?
C12 C13 1.4388(16) . ?
C13 C14 1.3492(15) . ?
C13 H13 0.959(15) . ?
C14 C15 1.4923(16) . ?
C15 H151 0.988(17) . ?
C15 H152 0.979(18) . ?
C15 H153 0.950(17) . ?

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
C5 N1 H1 119.3(11) . . ?
C5 N1 H2 117.7(10) . . ?
H1 N1 H2 119.5(15) . . ?
C1 O1 H10 109.4(12) . . ?
O2 C1 O1 122.79(11) . . ?
O2 C1 C2 123.72(10) . . ?
O1 C1 C2 113.48(10) . . ?
C7 C2 C3 118.69(10) . . ?
C7 C2 C1 118.67(10) . . ?
C3 C2 C1 122.62(10) . . ?
C4 C3 C2 120.54(10) . . ?
C4 C3 H3 119.2(9) . . ?
C2 C3 H3 120.2(9) . . ?
C3 C4 C5 120.73(11) . . ?
C3 C4 H4 119.8(9) . . ?
C5 C4 H4 119.5(9) . . ?
N1 C5 C6 120.56(11) . . ?
N1 C5 C4 121.00(11) . . ?
C6 C5 C4 118.42(11) . . ?
C7 C6 C5 120.28(10) . . ?
C7 C6 H6 121.2(9) . . ?
C5 C6 H6 118.5(9) . . ?
C6 C7 C2 121.33(10) . . ?
C6 C7 H7 119.8(8) . . ?
C2 C7 H7 118.8(8) . . ?
C11 N11 C12 125.12(10) . . ?
C11 N11 H11 115.4(10) . . ?
C12 N11 H11 119.5(10) . . ?
C11 N12 C14 123.08(9) . . ?
C11 N12 H12 115.0(10) . . ?
C14 N12 H12 121.9(10) . . ?
O11 C11 N12 121.66(10) . . ?
O11 C11 N11 121.88(10) . . ?
N12 C11 N11 116.46(10) . . ?
O12 C12 N11 119.24(10) . . ?
O12 C12 C13 125.76(10) . . ?
N11 C12 C13 115.00(9) . . ?
C14 C13 C12 120.65(10) . . ?
C14 C13 H13 121.2(9) . . ?
C12 C13 H13 118.0(9) . . ?
C13 C14 N12 119.57(10) . . ?
C13 C14 C15 125.31(10) . . ?
N12 C14 C15 115.10(10) . . ?
C14 C15 H151 110.7(10) . . ?
C14 C15 H152 109.3(10) . . ?
H151 C15 H152 108.9(14) . . ?
C14 C15 H153 110.7(10) . . ?
H151 C15 H153 109.6(14) . . ?
H152 C15 H153 107.5(14) . . ?

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
O1 H10 O11 0.89(2) 1.76(2) 2.6466(12) 172.4(19) .
N1 H1 O12 0.908(18) 2.071(18) 2.9763(15) 174.4(15) 8_465
N1 H2 O12 0.895(18) 2.132(18) 3.0035(14) 164.3(15) 7_566
N11 H11 O2 0.915(16) 1.925(17) 2.8305(13) 170.0(14) .
N12 H12 O11 0.897(17) 1.930(17) 2.8251(12) 175.0(15) 5_766

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        28.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.040
