# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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 1544196'
_audit_update_record             
;
2017-04-15 deposited with the CCDC.
2017-06-23 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C15 H12 N2 O), C7 H7 N O3, H2 O'
_chemical_formula_sum            'C37 H33 N5 O6'
_chemical_formula_weight         643.68

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                   13.6727(12)
_cell_length_b                   17.6172(15)
_cell_length_c                   14.8361(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 116.334(1)
_cell_angle_gamma                90.00
_cell_volume                     3202.8(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9945
_cell_measurement_theta_min      2.312
_cell_measurement_theta_max      30.521

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1352
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9728
_exptl_absorpt_correction_T_max  0.9818
_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         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            32373
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_av_sigmaI/netI    0.0236
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.31
_diffrn_reflns_theta_max         28.00
_reflns_number_total             7715
_reflns_number_gt                6313
_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)+(0.0471P)²+0.8148P] 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         7715
_refine_ls_number_parameters     565
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0382
_refine_ls_wR_factor_ref         0.1026
_refine_ls_wR_factor_gt          0.0955
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.027
_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
O5 O 0.32981(7) 0.52050(6) 0.17767(6) 0.0352(2) Uani 1 1 d . . .
H51 H 0.2610(16) 0.5364(10) 0.1603(13) 0.055(5) Uiso 1 1 d . . .
H52 H 0.3468(14) 0.5336(10) 0.1280(13) 0.052(5) Uiso 1 1 d . . .
N1 N 0.94835(9) 0.46529(7) 0.73036(8) 0.0409(3) Uani 1 1 d . . .
H1 H 1.0172(15) 0.4599(9) 0.7338(12) 0.052(5) Uiso 1 1 d . . .
H10 H 0.9345(14) 0.4478(10) 0.7809(13) 0.052(5) Uiso 1 1 d . . .
O1 O 0.60445(7) 0.52852(5) 0.27497(6) 0.0369(2) Uani 1 1 d . . .
O2 O 0.49658(7) 0.50521(6) 0.34930(7) 0.0427(2) Uani 1 1 d . . .
H2 H 0.4404(17) 0.5128(11) 0.2872(17) 0.074(6) Uiso 1 1 d . . .
O3 O 0.81568(8) 0.52196(6) 0.38326(7) 0.0379(2) Uani 1 1 d . . .
H3 H 0.7485(17) 0.5304(10) 0.3299(15) 0.064(5) Uiso 1 1 d . . .
C1 C 0.59325(10) 0.51358(7) 0.35156(8) 0.0301(2) Uani 1 1 d . . .
C2 C 0.68531(9) 0.50337(6) 0.44995(8) 0.0279(2) Uani 1 1 d . . .
C3 C 0.79332(9) 0.50710(6) 0.46194(8) 0.0279(2) Uani 1 1 d . . .
C4 C 0.88092(10) 0.49540(7) 0.55509(9) 0.0311(2) Uani 1 1 d . . .
C5 C 0.86358(9) 0.47821(7) 0.63878(8) 0.0304(2) Uani 1 1 d . . .
C6 C 0.75599(10) 0.47508(8) 0.62758(9) 0.0350(3) Uani 1 1 d . . .
C7 C 0.66999(10) 0.48711(8) 0.53551(9) 0.0342(3) Uani 1 1 d . . .
H4 H 0.9550(13) 0.4967(8) 0.5613(11) 0.041(4) Uiso 1 1 d . . .
H6 H 0.7422(13) 0.4619(9) 0.6837(12) 0.046(4) Uiso 1 1 d . . .
H7 H 0.5959(13) 0.4836(8) 0.5270(11) 0.042(4) Uiso 1 1 d . . .
O11 O 0.61872(6) 0.92008(5) 0.60620(6) 0.03136(18) Uani 1 1 d . . .
N11 N 0.62525(9) 0.88042(7) 0.46376(8) 0.0352(2) Uani 1 1 d . . .
H11 H 0.5936(13) 0.8573(9) 0.4066(13) 0.049(4) Uiso 1 1 d . . .
H12 H 0.6935(14) 0.8959(8) 0.4841(11) 0.040(4) Uiso 1 1 d . . .
N12 N 0.46968(7) 0.86300(5) 0.48369(7) 0.0263(2) Uani 1 1 d . . .
C10 C 0.57496(9) 0.88923(6) 0.52234(8) 0.0254(2) Uani 1 1 d . . .
C11 C 0.41580(8) 0.85572(6) 0.54682(8) 0.0264(2) Uani 1 1 d . . .
C12 C 0.42258(10) 0.78649(7) 0.59533(9) 0.0343(3) Uani 1 1 d . . .
C13 C 0.37114(12) 0.78179(9) 0.65852(10) 0.0444(3) Uani 1 1 d . . .
C14 C 0.31224(11) 0.84178(10) 0.66890(10) 0.0438(3) Uani 1 1 d . . .
C15 C 0.30290(10) 0.90864(8) 0.61665(9) 0.0368(3) Uani 1 1 d . . .
C16 C 0.35532(9) 0.91570(7) 0.55562(8) 0.0293(2) Uani 1 1 d . . .
C17 C 0.47671(12) 0.71999(8) 0.57870(12) 0.0465(3) Uani 1 1 d . . .
C21 C 0.42039(9) 0.82017(7) 0.39191(8) 0.0287(2) Uani 1 1 d . . .
C22 C 0.42823(10) 0.74118(7) 0.39673(10) 0.0376(3) Uani 1 1 d . . .
C23 C 0.37983(13) 0.70109(9) 0.30552(13) 0.0516(4) Uani 1 1 d . . .
C24 C 0.32294(13) 0.73839(11) 0.21532(12) 0.0565(4) Uani 1 1 d . . .
C25 C 0.31491(12) 0.81647(10) 0.21262(10) 0.0487(4) Uani 1 1 d . . .
C26 C 0.36441(10) 0.85802(8) 0.30130(9) 0.0355(3) Uani 1 1 d . . .
C27 C 0.47911(13) 0.70032(8) 0.49247(12) 0.0475(3) Uani 1 1 d . . .
H13 H 0.3772(14) 0.7346(10) 0.6922(13) 0.055(5) Uiso 1 1 d . . .
H14 H 0.2765(14) 0.8349(9) 0.7130(13) 0.055(5) Uiso 1 1 d . . .
H15 H 0.2613(13) 0.9517(9) 0.6231(11) 0.043(4) Uiso 1 1 d . . .
H16 H 0.3518(11) 0.9627(8) 0.5194(10) 0.034(4) Uiso 1 1 d . . .
H17 H 0.5078(14) 0.6838(10) 0.6372(13) 0.055(5) Uiso 1 1 d . . .
H23 H 0.3838(15) 0.6457(11) 0.3081(14) 0.067(5) Uiso 1 1 d . . .
H24 H 0.2892(16) 0.7085(11) 0.1519(15) 0.070(6) Uiso 1 1 d . . .
H25 H 0.2750(14) 0.8428(10) 0.1467(14) 0.058(5) Uiso 1 1 d . . .
H26 H 0.3611(12) 0.9130(9) 0.3030(11) 0.041(4) Uiso 1 1 d . . .
H27 H 0.5130(14) 0.6515(10) 0.4913(13) 0.056(5) Uiso 1 1 d . . .
O21 O 0.15219(7) 0.07272(5) 0.48241(6) 0.0373(2) Uani 1 1 d . . .
N21 N -0.02859(9) 0.09169(7) 0.42728(8) 0.0386(3) Uani 1 1 d . . .
H21 H -0.0804(14) 0.1147(10) 0.4372(13) 0.053(5) Uiso 1 1 d . . .
H22 H -0.0422(13) 0.0686(9) 0.3693(13) 0.046(4) Uiso 1 1 d . . .
N22 N 0.09539(7) 0.14283(5) 0.57786(7) 0.02588(19) Uani 1 1 d . . .
C30 C 0.07584(9) 0.10117(6) 0.49398(8) 0.0265(2) Uani 1 1 d . . .
C31 C 0.20435(9) 0.16648(6) 0.64258(8) 0.0267(2) Uani 1 1 d . . .
C32 C 0.23823(11) 0.23887(7) 0.63093(9) 0.0349(3) Uani 1 1 d . . .
C33 C 0.34745(13) 0.25869(10) 0.69475(12) 0.0493(4) Uani 1 1 d U . .
C34 C 0.41612(12) 0.20961(11) 0.76659(12) 0.0556(4) Uani 1 1 d U . .
C35 C 0.38008(12) 0.13899(10) 0.77702(11) 0.0521(4) Uani 1 1 d . . .
C36 C 0.27401(11) 0.11733(8) 0.71538(9) 0.0371(3) Uani 1 1 d . . .
C37 C 0.16456(16) 0.29390(8) 0.56011(11) 0.0497(4) Uani 1 1 d . . .
C41 C 0.01040(9) 0.18052(7) 0.59168(8) 0.0313(3) Uani 1 1 d . . .
C42 C -0.01012(11) 0.25687(8) 0.56554(9) 0.0426(3) Uani 1 1 d U . .
C43 C -0.09894(14) 0.28963(12) 0.57580(14) 0.0667(5) Uani 1 1 d U . .
C44 C -0.15842(13) 0.24877(15) 0.61360(16) 0.0767(7) Uani 1 1 d U . .
C45 C -0.13437(12) 0.17450(13) 0.64051(14) 0.0645(5) Uani 1 1 d U . .
C46 C -0.04999(11) 0.13952(10) 0.62941(10) 0.0435(3) Uani 1 1 d . . .
C47 C 0.05822(16) 0.30213(9) 0.53332(11) 0.0538(4) Uani 1 1 d . . .
H33 H 0.3688(15) 0.3082(11) 0.6847(13) 0.062(5) Uiso 1 1 d . . .
H34 H 0.4920(16) 0.2259(10) 0.8106(14) 0.064(5) Uiso 1 1 d . . .
H35 H 0.4323(17) 0.1043(11) 0.8292(15) 0.073(6) Uiso 1 1 d . . .
H36 H 0.2464(14) 0.0674(10) 0.7217(12) 0.049(4) Uiso 1 1 d . . .
H37 H 0.2000(15) 0.3315(11) 0.5381(14) 0.067(5) Uiso 1 1 d . . .
H43 H -0.1114(17) 0.3409(12) 0.5553(16) 0.076(6) Uiso 1 1 d . . .
H44 H -0.2186(18) 0.2734(12) 0.6205(16) 0.083(6) Uiso 1 1 d . . .
H45 H -0.1796(18) 0.1437(12) 0.6668(16) 0.082(6) Uiso 1 1 d . . .
H46 H -0.0311(15) 0.0833(11) 0.6480(14) 0.062(5) Uiso 1 1 d . . .
H47 H 0.0201(16) 0.3460(12) 0.4927(15) 0.074(6) 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
O5 H51 0.903(19) . ?
O5 H52 0.896(18) . ?
N1 C5 1.3579(14) . ?
N1 H1 0.924(18) . ?
N1 H10 0.906(18) . ?
O1 C1 1.2404(14) . ?
O2 C1 1.3155(15) . ?
O2 H2 0.91(2) . ?
O3 C3 1.3570(14) . ?
O3 H3 0.92(2) . ?
C1 C2 1.4551(15) . ?
C2 C7 1.4047(16) . ?
C2 C3 1.4083(16) . ?
C3 C4 1.3850(16) . ?
C4 C5 1.3967(17) . ?
C4 H4 0.975(16) . ?
C5 C6 1.4063(17) . ?
C6 C7 1.3669(16) . ?
C6 H6 0.959(16) . ?
C7 H7 0.965(16) . ?
O11 C10 1.2413(13) . ?
N11 C10 1.3350(15) . ?
N11 H11 0.865(17) . ?
N11 H12 0.886(17) . ?
N12 C10 1.3719(14) . ?
N12 C11 1.4313(14) . ?
N12 C21 1.4364(14) . ?
C11 C16 1.3832(17) . ?
C11 C12 1.3982(17) . ?
C12 C13 1.4020(19) . ?
C12 C17 1.464(2) . ?
C13 C14 1.378(2) . ?
C13 H13 0.955(18) . ?
C14 C15 1.385(2) . ?
C14 H14 0.982(18) . ?
C15 C16 1.3873(17) . ?
C15 H15 0.978(16) . ?
C16 H16 0.976(15) . ?
C17 C27 1.340(2) . ?
C17 H17 1.006(17) . ?
C21 C26 1.3874(17) . ?
C21 C22 1.3951(18) . ?
C22 C23 1.4048(19) . ?
C22 C27 1.464(2) . ?
C23 C24 1.380(3) . ?
C23 H23 0.977(19) . ?
C24 C25 1.379(3) . ?
C24 H24 1.00(2) . ?
C25 C26 1.3910(18) . ?
C25 H25 0.998(18) . ?
C26 H26 0.971(15) . ?
C27 H27 0.981(18) . ?
O21 C30 1.2368(14) . ?
N21 C30 1.3388(15) . ?
N21 H21 0.883(18) . ?
N21 H22 0.894(17) . ?
N22 C30 1.3651(14) . ?
N22 C41 1.4301(14) . ?
N22 C31 1.4303(13) . ?
C31 C36 1.3823(17) . ?
C31 C32 1.3936(17) . ?
C32 C33 1.412(2) . ?
C32 C37 1.456(2) . ?
C33 C34 1.370(3) . ?
C33 H33 0.953(19) . ?
C34 C35 1.372(3) . ?
C34 H34 0.992(19) . ?
C35 C36 1.3815(19) . ?
C35 H35 1.00(2) . ?
C36 H36 0.978(17) . ?
C37 C47 1.334(3) . ?
C37 H37 0.96(2) . ?
C41 C46 1.388(2) . ?
C41 C42 1.3934(19) . ?
C42 C43 1.412(2) . ?
C42 C47 1.461(2) . ?
C43 C44 1.378(3) . ?
C43 H43 0.94(2) . ?
C44 C45 1.365(3) . ?
C44 H44 0.97(2) . ?
C45 C46 1.381(2) . ?
C45 H45 1.02(2) . ?
C46 H46 1.030(18) . ?
C47 H47 0.98(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
H51 O5 H52 107.6(15) . . ?
C5 N1 H1 117.9(10) . . ?
C5 N1 H10 119.1(11) . . ?
H1 N1 H10 120.1(15) . . ?
C1 O2 H2 113.4(13) . . ?
C3 O3 H3 104.5(12) . . ?
O1 C1 O2 122.10(10) . . ?
O1 C1 C2 122.80(11) . . ?
O2 C1 C2 115.09(10) . . ?
C7 C2 C3 117.63(10) . . ?
C7 C2 C1 121.48(11) . . ?
C3 C2 C1 120.86(10) . . ?
O3 C3 C4 117.51(11) . . ?
O3 C3 C2 121.61(10) . . ?
C4 C3 C2 120.89(10) . . ?
C3 C4 C5 120.44(11) . . ?
C3 C4 H4 119.5(9) . . ?
C5 C4 H4 120.0(9) . . ?
N1 C5 C4 121.31(11) . . ?
N1 C5 C6 119.70(11) . . ?
C4 C5 C6 118.99(10) . . ?
C7 C6 C5 120.20(11) . . ?
C7 C6 H6 119.4(10) . . ?
C5 C6 H6 120.3(10) . . ?
C6 C7 C2 121.84(11) . . ?
C6 C7 H7 120.6(9) . . ?
C2 C7 H7 117.6(9) . . ?
C10 N11 H11 121.1(11) . . ?
C10 N11 H12 120.7(10) . . ?
H11 N11 H12 118.2(15) . . ?
C10 N12 C11 120.39(9) . . ?
C10 N12 C21 122.50(9) . . ?
C11 N12 C21 114.33(9) . . ?
O11 C10 N11 123.02(10) . . ?
O11 C10 N12 121.08(10) . . ?
N11 C10 N12 115.89(10) . . ?
C16 C11 C12 121.59(11) . . ?
C16 C11 N12 119.74(10) . . ?
C12 C11 N12 118.63(10) . . ?
C11 C12 C13 117.21(12) . . ?
C11 C12 C17 122.30(12) . . ?
C13 C12 C17 120.43(12) . . ?
C14 C13 C12 121.39(13) . . ?
C14 C13 H13 121.9(11) . . ?
C12 C13 H13 116.6(11) . . ?
C13 C14 C15 120.21(12) . . ?
C13 C14 H14 117.9(10) . . ?
C15 C14 H14 121.9(10) . . ?
C14 C15 C16 119.71(13) . . ?
C14 C15 H15 121.3(9) . . ?
C16 C15 H15 119.0(9) . . ?
C11 C16 C15 119.78(12) . . ?
C11 C16 H16 118.8(8) . . ?
C15 C16 H16 121.4(8) . . ?
C27 C17 C12 126.60(13) . . ?
C27 C17 H17 118.7(10) . . ?
C12 C17 H17 114.4(10) . . ?
C26 C21 C22 121.72(11) . . ?
C26 C21 N12 119.42(11) . . ?
C22 C21 N12 118.84(11) . . ?
C21 C22 C23 117.36(13) . . ?
C21 C22 C27 122.20(12) . . ?
C23 C22 C27 120.36(13) . . ?
C24 C23 C22 121.11(15) . . ?
C24 C23 H23 120.7(11) . . ?
C22 C23 H23 118.0(11) . . ?
C25 C24 C23 120.43(13) . . ?
C25 C24 H24 120.2(11) . . ?
C23 C24 H24 119.4(11) . . ?
C24 C25 C26 119.89(15) . . ?
C24 C25 H25 119.6(10) . . ?
C26 C25 H25 120.5(10) . . ?
C21 C26 C25 119.44(14) . . ?
C21 C26 H26 117.8(9) . . ?
C25 C26 H26 122.8(9) . . ?
C17 C27 C22 126.65(13) . . ?
C17 C27 H27 117.1(10) . . ?
C22 C27 H27 116.0(10) . . ?
C30 N21 H21 119.4(11) . . ?
C30 N21 H22 117.8(10) . . ?
H21 N21 H22 122.0(15) . . ?
C30 N22 C41 122.50(9) . . ?
C30 N22 C31 119.54(9) . . ?
C41 N22 C31 116.05(9) . . ?
O21 C30 N21 122.42(10) . . ?
O21 C30 N22 120.55(10) . . ?
N21 C30 N22 117.02(10) . . ?
C36 C31 C32 121.23(11) . . ?
C36 C31 N22 119.57(11) . . ?
C32 C31 N22 119.20(10) . . ?
C31 C32 C33 117.00(13) . . ?
C31 C32 C37 122.50(12) . . ?
C33 C32 C37 120.44(13) . . ?
C34 C33 C32 121.43(15) . . ?
C34 C33 H33 123.2(11) . . ?
C32 C33 H33 115.3(11) . . ?
C33 C34 C35 120.24(13) . . ?
C33 C34 H34 119.0(11) . . ?
C35 C34 H34 120.7(11) . . ?
C34 C35 C36 120.00(15) . . ?
C34 C35 H35 118.4(11) . . ?
C36 C35 H35 121.6(12) . . ?
C35 C36 C31 120.09(14) . . ?
C35 C36 H36 121.4(10) . . ?
C31 C36 H36 118.5(10) . . ?
C47 C37 C32 126.94(14) . . ?
C47 C37 H37 118.1(11) . . ?
C32 C37 H37 114.4(12) . . ?
C46 C41 C42 122.16(12) . . ?
C46 C41 N22 118.87(12) . . ?
C42 C41 N22 118.97(12) . . ?
C41 C42 C43 116.16(16) . . ?
C41 C42 C47 122.62(13) . . ?
C43 C42 C47 121.17(16) . . ?
C44 C43 C42 121.42(18) . . ?
C44 C43 H43 125.2(13) . . ?
C42 C43 H43 113.4(13) . . ?
C45 C44 C43 120.71(15) . . ?
C45 C44 H44 120.1(13) . . ?
C43 C44 H44 119.2(13) . . ?
C44 C45 C46 119.91(19) . . ?
C44 C45 H45 120.8(12) . . ?
C46 C45 H45 119.2(13) . . ?
C45 C46 C41 119.59(17) . . ?
C45 C46 H46 121.4(11) . . ?
C41 C46 H46 119.0(10) . . ?
C37 C47 C42 127.87(13) . . ?
C37 C47 H47 118.9(12) . . ?
C42 C47 H47 113.0(12) . . ?

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 179.45(12) . . . . ?
O2 C1 C2 C7 -1.06(17) . . . . ?
O1 C1 C2 C3 -2.62(18) . . . . ?
O2 C1 C2 C3 176.87(11) . . . . ?
C7 C2 C3 O3 179.53(11) . . . . ?
C1 C2 C3 O3 1.53(18) . . . . ?
C7 C2 C3 C4 -0.27(17) . . . . ?
C1 C2 C3 C4 -178.28(11) . . . . ?
O3 C3 C4 C5 -178.59(11) . . . . ?
C2 C3 C4 C5 1.22(18) . . . . ?
C3 C4 C5 N1 178.88(12) . . . . ?
C3 C4 C5 C6 -1.78(19) . . . . ?
N1 C5 C6 C7 -179.23(13) . . . . ?
C4 C5 C6 C7 1.4(2) . . . . ?
C5 C6 C7 C2 -0.5(2) . . . . ?
C3 C2 C7 C6 -0.09(19) . . . . ?
C1 C2 C7 C6 177.90(12) . . . . ?
C11 N12 C10 O11 -13.40(16) . . . . ?
C21 N12 C10 O11 -173.41(10) . . . . ?
C11 N12 C10 N11 167.59(10) . . . . ?
C21 N12 C10 N11 7.58(16) . . . . ?
C10 N12 C11 C16 90.96(13) . . . . ?
C21 N12 C11 C16 -107.48(12) . . . . ?
C10 N12 C11 C12 -91.40(13) . . . . ?
C21 N12 C11 C12 70.15(13) . . . . ?
C16 C11 C12 C13 -3.91(17) . . . . ?
N12 C11 C12 C13 178.50(10) . . . . ?
C16 C11 C12 C17 173.55(11) . . . . ?
N12 C11 C12 C17 -4.04(17) . . . . ?
C11 C12 C13 C14 2.82(19) . . . . ?
C17 C12 C13 C14 -174.70(13) . . . . ?
C12 C13 C14 C15 -0.1(2) . . . . ?
C13 C14 C15 C16 -1.57(19) . . . . ?
C12 C11 C16 C15 2.32(16) . . . . ?
N12 C11 C16 C15 179.88(10) . . . . ?
C14 C15 C16 C11 0.50(17) . . . . ?
C11 C12 C17 C27 -34.3(2) . . . . ?
C13 C12 C17 C27 143.06(16) . . . . ?
C10 N12 C21 C26 -90.38(14) . . . . ?
C11 N12 C21 C26 108.51(12) . . . . ?
C10 N12 C21 C22 91.00(14) . . . . ?
C11 N12 C21 C22 -70.12(14) . . . . ?
C26 C21 C22 C23 1.88(19) . . . . ?
N12 C21 C22 C23 -179.53(11) . . . . ?
C26 C21 C22 C27 -174.76(12) . . . . ?
N12 C21 C22 C27 3.83(18) . . . . ?
C21 C22 C23 C24 -2.7(2) . . . . ?
C27 C22 C23 C24 174.05(14) . . . . ?
C22 C23 C24 C25 1.8(2) . . . . ?
C23 C24 C25 C26 0.0(2) . . . . ?
C22 C21 C26 C25 -0.21(19) . . . . ?
N12 C21 C26 C25 -178.79(11) . . . . ?
C24 C25 C26 C21 -0.8(2) . . . . ?
C12 C17 C27 C22 0.1(3) . . . . ?
C21 C22 C27 C17 34.3(2) . . . . ?
C23 C22 C27 C17 -142.27(16) . . . . ?
C41 N22 C30 O21 176.19(11) . . . . ?
C31 N22 C30 O21 12.52(17) . . . . ?
C41 N22 C30 N21 -5.13(17) . . . . ?
C31 N22 C30 N21 -168.80(11) . . . . ?
C30 N22 C31 C36 -83.98(14) . . . . ?
C41 N22 C31 C36 111.32(12) . . . . ?
C30 N22 C31 C32 96.04(13) . . . . ?
C41 N22 C31 C32 -68.66(13) . . . . ?
C36 C31 C32 C33 1.77(17) . . . . ?
N22 C31 C32 C33 -178.25(10) . . . . ?
C36 C31 C32 C37 -175.33(12) . . . . ?
N22 C31 C32 C37 4.65(17) . . . . ?
C31 C32 C33 C34 -1.62(19) . . . . ?
C37 C32 C33 C34 175.54(13) . . . . ?
C32 C33 C34 C35 1.0(2) . . . . ?
C33 C34 C35 C36 -0.4(2) . . . . ?
C34 C35 C36 C31 0.6(2) . . . . ?
C32 C31 C36 C35 -1.29(18) . . . . ?
N22 C31 C36 C35 178.73(11) . . . . ?
C31 C32 C37 C47 33.1(2) . . . . ?
C33 C32 C37 C47 -143.91(16) . . . . ?
C30 N22 C41 C46 83.57(14) . . . . ?
C31 N22 C41 C46 -112.23(12) . . . . ?
C30 N22 C41 C42 -95.53(13) . . . . ?
C31 N22 C41 C42 68.67(13) . . . . ?
C46 C41 C42 C43 -2.44(18) . . . . ?
N22 C41 C42 C43 176.63(11) . . . . ?
C46 C41 C42 C47 175.04(12) . . . . ?
N22 C41 C42 C47 -5.89(17) . . . . ?
C41 C42 C43 C44 2.6(2) . . . . ?
C47 C42 C43 C44 -174.87(14) . . . . ?
C42 C43 C44 C45 -1.3(2) . . . . ?
C43 C44 C45 C46 -0.3(2) . . . . ?
C44 C45 C46 C41 0.6(2) . . . . ?
C42 C41 C46 C45 0.91(19) . . . . ?
N22 C41 C46 C45 -178.16(11) . . . . ?
C32 C37 C47 C42 -2.2(3) . . . . ?
C41 C42 C47 C37 -29.8(2) . . . . ?
C43 C42 C47 C37 147.55(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
O5 H51 O11 0.903(19) 1.91(2) 2.7991(12) 170.1(16) 4_575
O5 H52 O21 0.896(18) 1.783(18) 2.6583(12) 165.0(16) 2
N1 H10 O11 0.906(18) 2.157(18) 3.0542(15) 170.8(15) 2_646
N11 H12 O21 0.886(17) 2.019(17) 2.9022(14) 174.4(14) 3_666
N21 H22 O1 0.894(17) 2.046(17) 2.9252(13) 167.5(15) 2_545
O2 H2 O5 0.91(2) 1.66(2) 2.5699(12) 174(2) .
O3 H3 O1 0.92(2) 1.77(2) 2.6113(13) 151.3(17) .

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        28.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.255
_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_x
_database_code_depnum_ccdc_archive 'CCDC 1544195'
_audit_update_record             
;
2017-04-15 deposited with the CCDC.
2017-06-23 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H12 N2 O, C7 H7 N O3'
_chemical_formula_sum            'C22 H19 N3 O4'
_chemical_formula_weight         389.40

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                   27.427(5)
_cell_length_b                   7.6402(15)
_cell_length_c                   21.038(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 119.263(2)
_cell_angle_gamma                90.00
_cell_volume                     3845.8(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9985
_cell_measurement_theta_min      2.220
_cell_measurement_theta_max      30.498

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1632
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9722
_exptl_absorpt_correction_T_max  0.9814
_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            20588
_diffrn_reflns_av_R_equivalents  0.0199
_diffrn_reflns_av_sigmaI/netI    0.0162
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.03
_diffrn_reflns_theta_max         29.00
_reflns_number_total             5123
_reflns_number_gt                4512
_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)+(0.0551P)²+1.9988P] 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         5123
_refine_ls_number_parameters     338
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0385
_refine_ls_wR_factor_ref         0.1058
_refine_ls_wR_factor_gt          0.1018
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_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 0.71112(5) -0.25120(15) 0.65423(6) 0.0411(3) Uani 1 1 d . . .
O1 O 0.57587(3) 0.44174(10) 0.63728(4) 0.02883(17) Uani 1 1 d . . .
O2 O 0.50779(3) 0.27114(10) 0.55522(4) 0.02976(18) Uani 1 1 d . . .
O3 O 0.67572(3) 0.31939(10) 0.71091(4) 0.03129(18) Uani 1 1 d . . .
C1 C 0.56010(4) 0.30032(13) 0.60420(5) 0.02170(18) Uani 1 1 d . . .
C2 C 0.59856(4) 0.15489(12) 0.61793(5) 0.01997(18) Uani 1 1 d . . .
C3 C 0.65535(4) 0.17037(13) 0.67114(5) 0.02144(18) Uani 1 1 d . . .
C4 C 0.69256(4) 0.03492(13) 0.68372(5) 0.0244(2) Uani 1 1 d . . .
C5 C 0.67431(4) -0.11980(14) 0.64350(5) 0.0257(2) Uani 1 1 d . . .
C6 C 0.61727(4) -0.13911(14) 0.59137(6) 0.0290(2) Uani 1 1 d . . .
C7 C 0.58096(4) -0.00391(14) 0.57952(5) 0.0259(2) Uani 1 1 d . . .
H1 H 0.7458(7) -0.235(2) 0.6862(9) 0.048(4) Uiso 1 1 d . . .
H2 H 0.4842(8) 0.369(3) 0.5508(10) 0.066(5) Uiso 1 1 d . . .
H3 H 0.6447(7) 0.397(2) 0.6919(9) 0.055(5) Uiso 1 1 d . . .
H4 H 0.7306(6) 0.051(2) 0.7194(8) 0.038(4) Uiso 1 1 d . . .
H6 H 0.6045(6) -0.246(2) 0.5654(8) 0.039(4) Uiso 1 1 d . . .
H7 H 0.5415(7) -0.018(2) 0.5432(8) 0.040(4) Uiso 1 1 d . . .
H10 H 0.7004(7) -0.341(2) 0.6262(9) 0.043(4) Uiso 1 1 d . . .
N11 N 0.49219(4) 0.69516(15) 0.62181(6) 0.0385(3) Uani 1 1 d . . .
N12 N 0.39642(3) 0.71355(11) 0.57406(5) 0.02389(18) Uani 1 1 d . . .
O11 O 0.43448(3) 0.49928(10) 0.53772(4) 0.03031(18) Uani 1 1 d . . .
C10 C 0.44132(4) 0.62983(13) 0.57656(5) 0.0247(2) Uani 1 1 d . . .
C11 C 0.34137(4) 0.64225(13) 0.53141(5) 0.02274(19) Uani 1 1 d . . .
C12 C 0.31684(4) 0.55128(13) 0.56618(6) 0.0253(2) Uani 1 1 d . . .
C13 C 0.26393(5) 0.47644(14) 0.52214(7) 0.0319(2) Uani 1 1 d . . .
C14 C 0.23639(5) 0.49788(15) 0.44733(7) 0.0340(3) Uani 1 1 d . . .
C15 C 0.26048(5) 0.59575(16) 0.41447(6) 0.0331(2) Uani 1 1 d . . .
C16 C 0.31319(5) 0.66717(15) 0.45651(6) 0.0287(2) Uani 1 1 d . . .
C17 C 0.34276(5) 0.53722(14) 0.64545(6) 0.0310(2) Uani 1 1 d . . .
C21 C 0.40268(4) 0.85546(13) 0.62199(5) 0.02318(19) Uani 1 1 d . . .
C22 C 0.39517(4) 0.82283(13) 0.68229(5) 0.0252(2) Uani 1 1 d . . .
C23 C 0.40464(5) 0.96227(15) 0.73047(6) 0.0311(2) Uani 1 1 d . . .
C24 C 0.41916(5) 1.12672(16) 0.71772(6) 0.0348(2) Uani 1 1 d . . .
C25 C 0.42491(5) 1.15736(15) 0.65656(7) 0.0344(2) Uani 1 1 d . . .
C26 C 0.41659(5) 1.02124(14) 0.60857(6) 0.0290(2) Uani 1 1 d . . .
C27 C 0.37649(5) 0.65395(15) 0.69529(6) 0.0310(2) Uani 1 1 d . . .
H11 H 0.4957(7) 0.784(2) 0.6498(9) 0.049(4) Uiso 1 1 d . . .
H12 H 0.5218(7) 0.632(2) 0.6257(9) 0.052(5) Uiso 1 1 d . . .
H13 H 0.2465(6) 0.409(2) 0.5457(8) 0.039(4) Uiso 1 1 d . . .
H14 H 0.2001(6) 0.445(2) 0.4196(8) 0.041(4) Uiso 1 1 d . . .
H15 H 0.2403(6) 0.614(2) 0.3617(8) 0.038(4) Uiso 1 1 d . . .
H16 H 0.3316(6) 0.734(2) 0.4360(8) 0.041(4) Uiso 1 1 d . . .
H17 H 0.3308(6) 0.436(2) 0.6630(8) 0.041(4) Uiso 1 1 d . . .
H23 H 0.4005(6) 0.9435(19) 0.7724(8) 0.037(4) Uiso 1 1 d . . .
H24 H 0.4257(6) 1.222(2) 0.7510(8) 0.040(4) Uiso 1 1 d . . .
H25 H 0.4357(6) 1.272(2) 0.6468(8) 0.044(4) Uiso 1 1 d . . .
H26 H 0.4208(6) 1.0375(19) 0.5661(8) 0.032(3) Uiso 1 1 d . . .
H27 H 0.3870(7) 0.630(2) 0.7462(9) 0.045(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 1.3620(14) . ?
N1 H1 0.865(17) . ?
N1 H10 0.860(17) . ?
O1 C1 1.2428(12) . ?
O2 C1 1.3132(12) . ?
O2 H2 0.96(2) . ?
O3 C3 1.3607(12) . ?
O3 H3 0.948(18) . ?
C1 C2 1.4603(13) . ?
C2 C7 1.4059(13) . ?
C2 C3 1.4102(13) . ?
C3 C4 1.3852(13) . ?
C4 C5 1.3964(14) . ?
C4 H4 0.949(15) . ?
C5 C6 1.4123(14) . ?
C6 C7 1.3704(14) . ?
C6 H6 0.952(16) . ?
C7 H7 0.980(16) . ?
N11 C10 1.3429(14) . ?
N11 H11 0.871(18) . ?
N11 H12 0.912(18) . ?
N12 C10 1.3658(12) . ?
N12 C21 1.4326(12) . ?
N12 C11 1.4341(13) . ?
O11 C10 1.2441(12) . ?
C11 C16 1.3877(15) . ?
C11 C12 1.3972(14) . ?
C12 C13 1.4060(15) . ?
C12 C17 1.4625(15) . ?
C13 C14 1.3828(18) . ?
C13 H13 0.984(15) . ?
C14 C15 1.3857(18) . ?
C14 H14 0.963(16) . ?
C15 C16 1.3857(16) . ?
C15 H15 0.979(15) . ?
C16 H16 0.954(16) . ?
C17 C27 1.3425(17) . ?
C17 H17 0.979(16) . ?
C21 C26 1.3910(15) . ?
C21 C22 1.4032(14) . ?
C22 C23 1.4045(15) . ?
C22 C27 1.4626(15) . ?
C23 C24 1.3834(18) . ?
C23 H23 0.952(15) . ?
C24 C25 1.3905(18) . ?
C24 H24 0.966(15) . ?
C25 C26 1.3884(16) . ?
C25 H25 0.980(16) . ?
C26 H26 0.963(14) . ?
C27 H27 0.980(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
C5 N1 H1 118.0(12) . . ?
C5 N1 H10 120.0(11) . . ?
H1 N1 H10 121.6(16) . . ?
C1 O2 H2 111.6(11) . . ?
C3 O3 H3 104.3(11) . . ?
O1 C1 O2 122.32(9) . . ?
O1 C1 C2 122.05(8) . . ?
O2 C1 C2 115.62(8) . . ?
C7 C2 C3 117.66(8) . . ?
C7 C2 C1 122.08(8) . . ?
C3 C2 C1 120.26(8) . . ?
O3 C3 C4 117.70(8) . . ?
O3 C3 C2 121.37(8) . . ?
C4 C3 C2 120.92(9) . . ?
C3 C4 C5 120.28(9) . . ?
C3 C4 H4 118.3(9) . . ?
C5 C4 H4 121.4(9) . . ?
N1 C5 C4 120.42(10) . . ?
N1 C5 C6 120.11(10) . . ?
C4 C5 C6 119.46(9) . . ?
C7 C6 C5 119.55(10) . . ?
C7 C6 H6 121.0(9) . . ?
C5 C6 H6 119.5(9) . . ?
C6 C7 C2 122.08(9) . . ?
C6 C7 H7 119.2(9) . . ?
C2 C7 H7 118.7(9) . . ?
C10 N11 H11 120.2(11) . . ?
C10 N11 H12 116.1(11) . . ?
H11 N11 H12 123.2(15) . . ?
C10 N12 C21 122.12(8) . . ?
C10 N12 C11 119.99(8) . . ?
C21 N12 C11 117.08(8) . . ?
O11 C10 N11 122.31(9) . . ?
O11 C10 N12 120.44(9) . . ?
N11 C10 N12 117.26(9) . . ?
C16 C11 C12 121.28(10) . . ?
C16 C11 N12 119.34(9) . . ?
C12 C11 N12 119.38(9) . . ?
C11 C12 C13 117.61(10) . . ?
C11 C12 C17 122.91(10) . . ?
C13 C12 C17 119.44(10) . . ?
C14 C13 C12 121.02(11) . . ?
C14 C13 H13 120.3(9) . . ?
C12 C13 H13 118.6(9) . . ?
C13 C14 C15 120.23(11) . . ?
C13 C14 H14 117.9(9) . . ?
C15 C14 H14 121.9(9) . . ?
C14 C15 C16 119.81(11) . . ?
C14 C15 H15 120.0(9) . . ?
C16 C15 H15 120.2(9) . . ?
C15 C16 C11 119.93(11) . . ?
C15 C16 H16 122.5(9) . . ?
C11 C16 H16 117.5(9) . . ?
C27 C17 C12 127.38(10) . . ?
C27 C17 H17 117.4(9) . . ?
C12 C17 H17 114.9(9) . . ?
C26 C21 C22 121.42(9) . . ?
C26 C21 N12 119.78(9) . . ?
C22 C21 N12 118.80(9) . . ?
C21 C22 C23 117.42(10) . . ?
C21 C22 C27 123.06(9) . . ?
C23 C22 C27 119.49(9) . . ?
C24 C23 C22 121.21(10) . . ?
C24 C23 H23 119.4(9) . . ?
C22 C23 H23 119.3(9) . . ?
C23 C24 C25 120.39(10) . . ?
C23 C24 H24 121.0(9) . . ?
C25 C24 H24 118.6(9) . . ?
C26 C25 C24 119.61(11) . . ?
C26 C25 H25 118.6(9) . . ?
C24 C25 H25 121.8(9) . . ?
C25 C26 C21 119.88(10) . . ?
C25 C26 H26 121.8(9) . . ?
C21 C26 H26 118.3(9) . . ?
C17 C27 C22 127.63(10) . . ?
C17 C27 H27 117.0(9) . . ?
C22 C27 H27 115.1(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 -178.74(10) . . . . ?
O2 C1 C2 C7 1.91(14) . . . . ?
O1 C1 C2 C3 1.37(15) . . . . ?
O2 C1 C2 C3 -177.98(9) . . . . ?
C7 C2 C3 O3 -179.76(9) . . . . ?
C1 C2 C3 O3 0.14(14) . . . . ?
C7 C2 C3 C4 1.46(14) . . . . ?
C1 C2 C3 C4 -178.65(9) . . . . ?
O3 C3 C4 C5 -178.66(9) . . . . ?
C2 C3 C4 C5 0.17(15) . . . . ?
C3 C4 C5 N1 178.05(11) . . . . ?
C3 C4 C5 C6 -1.85(16) . . . . ?
N1 C5 C6 C7 -178.03(11) . . . . ?
C4 C5 C6 C7 1.87(16) . . . . ?
C5 C6 C7 C2 -0.21(17) . . . . ?
C3 C2 C7 C6 -1.44(16) . . . . ?
C1 C2 C7 C6 178.66(10) . . . . ?
C21 N12 C10 O11 174.92(9) . . . . ?
C11 N12 C10 O11 5.54(15) . . . . ?
C21 N12 C10 N11 -5.55(15) . . . . ?
C11 N12 C10 N11 -174.92(10) . . . . ?
C10 N12 C11 C16 -78.88(12) . . . . ?
C21 N12 C11 C16 111.22(10) . . . . ?
C10 N12 C11 C12 102.06(11) . . . . ?
C21 N12 C11 C12 -67.84(12) . . . . ?
C16 C11 C12 C13 3.85(14) . . . . ?
N12 C11 C12 C13 -177.11(9) . . . . ?
C16 C11 C12 C17 -173.72(10) . . . . ?
N12 C11 C12 C17 5.32(14) . . . . ?
C11 C12 C13 C14 -2.34(15) . . . . ?
C17 C12 C13 C14 175.32(10) . . . . ?
C12 C13 C14 C15 -0.68(16) . . . . ?
C13 C14 C15 C16 2.27(16) . . . . ?
C14 C15 C16 C11 -0.78(16) . . . . ?
C12 C11 C16 C15 -2.35(15) . . . . ?
N12 C11 C16 C15 178.60(9) . . . . ?
C11 C12 C17 C27 30.33(17) . . . . ?
C13 C12 C17 C27 -147.20(12) . . . . ?
C10 N12 C21 C26 77.31(13) . . . . ?
C11 N12 C21 C26 -113.01(11) . . . . ?
C10 N12 C21 C22 -101.97(12) . . . . ?
C11 N12 C21 C22 67.70(12) . . . . ?
C26 C21 C22 C23 -2.73(15) . . . . ?
N12 C21 C22 C23 176.54(9) . . . . ?
C26 C21 C22 C27 175.29(10) . . . . ?
N12 C21 C22 C27 -5.44(15) . . . . ?
C21 C22 C23 C24 1.91(16) . . . . ?
C27 C22 C23 C24 -176.19(10) . . . . ?
C22 C23 C24 C25 -0.22(18) . . . . ?
C23 C24 C25 C26 -0.71(19) . . . . ?
C24 C25 C26 C21 -0.10(18) . . . . ?
C22 C21 C26 C25 1.87(16) . . . . ?
N12 C21 C26 C25 -177.39(10) . . . . ?
C12 C17 C27 C22 0.2(2) . . . . ?
C21 C22 C27 C17 -30.58(17) . . . . ?
C23 C22 C27 C17 147.40(12) . . . . ?

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
N11 H12 O1 0.912(18) 2.006(18) 2.8970(13) 164.9(16) .
O2 H2 O11 0.96(2) 1.60(2) 2.5481(11) 167.4(18) .
O3 H3 O1 0.948(18) 1.698(18) 2.5740(11) 152.0(16) .
N1 H1 O3 0.865(17) 2.221(18) 3.0600(14) 163.4(15) 4_646

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        29.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.041
####################################################################### 
# 
# 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 1544197'
_audit_update_record             
;
2017-04-15 deposited with the CCDC.
2017-06-23 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C15 H12 N2 O), C7 H7 N O3, C H4 O'
_chemical_formula_sum            'C38 H35 N5 O6'
_chemical_formula_weight         657.71

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                   12.6443(18)
_cell_length_b                   7.5232(11)
_cell_length_c                   34.674(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.811(3)
_cell_angle_gamma                90.00
_cell_volume                     3275.1(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    183(2)
_cell_measurement_reflns_used    4863
_cell_measurement_theta_min      2.118
_cell_measurement_theta_max      26.714

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1384
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9642
_exptl_absorpt_correction_T_max  0.9819
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      183(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         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            24975
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_sigmaI/netI    0.0341
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_theta_min         2.37
_diffrn_reflns_theta_max         26.00
_reflns_number_total             6390
_reflns_number_gt                5050
_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)+(0.0376P)²+0.8058P] 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     SHELXL
_refine_ls_extinction_coef       0.0013(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6390
_refine_ls_number_parameters     583
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0377
_refine_ls_wR_factor_ref         0.0915
_refine_ls_wR_factor_gt          0.0839
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_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
O11 O 0.72283(8) 0.24545(13) 0.10590(3) 0.0299(2) Uani 1 1 d . . .
N11 N 0.87546(11) 0.09775(18) 0.09990(4) 0.0343(3) Uani 1 1 d . . .
N12 N 0.82945(9) 0.34661(15) 0.06241(3) 0.0262(3) Uani 1 1 d . . .
C10 C 0.80559(11) 0.22919(18) 0.09021(4) 0.0247(3) Uani 1 1 d . . .
C11 C 0.75706(11) 0.48963(18) 0.05122(4) 0.0240(3) Uani 1 1 d . . .
C12 C 0.68922(11) 0.47745(19) 0.01644(4) 0.0280(3) Uani 1 1 d . . .
C13 C 0.62026(13) 0.6205(2) 0.00660(5) 0.0348(4) Uani 1 1 d . . .
C14 C 0.61907(13) 0.7668(2) 0.03017(5) 0.0376(4) Uani 1 1 d . . .
C15 C 0.68596(13) 0.7753(2) 0.06473(5) 0.0344(4) Uani 1 1 d . . .
C16 C 0.75534(12) 0.6372(2) 0.07503(4) 0.0283(3) Uani 1 1 d . . .
C17 C 0.68787(14) 0.3228(2) -0.00913(5) 0.0362(4) Uani 1 1 d . . .
C21 C 0.91094(12) 0.31163(19) 0.03781(4) 0.0280(3) Uani 1 1 d . . .
C22 C 0.88105(13) 0.24110(19) 0.00085(5) 0.0322(4) Uani 1 1 d . . .
C23 C 0.96259(15) 0.1970(2) -0.02146(5) 0.0399(4) Uani 1 1 d . . .
C24 C 1.06791(15) 0.2262(2) -0.00793(6) 0.0429(4) Uani 1 1 d . . .
C25 C 1.09545(14) 0.3013(2) 0.02798(6) 0.0422(4) Uani 1 1 d . . .
C26 C 1.01649(12) 0.3453(2) 0.05099(5) 0.0352(4) Uani 1 1 d . . .
C27 C 0.77008(14) 0.2190(2) -0.01529(5) 0.0384(4) Uani 1 1 d . . .
H11 H 0.9370(15) 0.089(2) 0.0905(5) 0.045(5) Uiso 1 1 d . . .
H12 H 0.8609(13) 0.022(2) 0.1191(5) 0.040(5) Uiso 1 1 d . . .
H13 H 0.5736(13) 0.613(2) -0.0176(5) 0.039(5) Uiso 1 1 d . . .
H14 H 0.5707(14) 0.865(3) 0.0230(5) 0.049(5) Uiso 1 1 d . . .
H15 H 0.6842(12) 0.881(2) 0.0813(5) 0.038(4) Uiso 1 1 d . . .
H16 H 0.8042(12) 0.641(2) 0.0988(5) 0.032(4) Uiso 1 1 d . . .
H17 H 0.6202(15) 0.300(2) -0.0258(5) 0.053(5) Uiso 1 1 d . . .
H23 H 0.9423(13) 0.146(2) -0.0471(5) 0.046(5) Uiso 1 1 d . . .
H24 H 1.1212(15) 0.193(2) -0.0243(5) 0.054(5) Uiso 1 1 d . . .
H25 H 1.1701(16) 0.324(2) 0.0383(5) 0.052(5) Uiso 1 1 d . . .
H26 H 1.0344(12) 0.403(2) 0.0757(5) 0.032(4) Uiso 1 1 d . . .
H27 H 0.7563(14) 0.130(2) -0.0357(5) 0.048(5) Uiso 1 1 d . . .
O21 O 0.81651(8) 0.86330(14) 0.16341(3) 0.0346(3) Uani 1 1 d . . .
N21 N 0.66225(12) 1.00760(18) 0.16691(4) 0.0339(3) Uani 1 1 d . . .
N22 N 0.69786(10) 0.74522(15) 0.20075(3) 0.0279(3) Uani 1 1 d . . .
C30 C 0.72882(12) 0.87283(19) 0.17633(4) 0.0269(3) Uani 1 1 d . . .
C31 C 0.59816(12) 0.75239(18) 0.21672(4) 0.0275(3) Uani 1 1 d . . .
C32 C 0.59898(13) 0.78302(19) 0.25647(4) 0.0324(4) Uani 1 1 d . . .
C33 C 0.49991(15) 0.7938(2) 0.27086(5) 0.0404(4) Uani 1 1 d . . .
C34 C 0.40586(15) 0.7740(2) 0.24704(6) 0.0435(4) Uani 1 1 d . . .
C35 C 0.40700(14) 0.7440(2) 0.20774(6) 0.0400(4) Uani 1 1 d . . .
C36 C 0.50339(13) 0.7309(2) 0.19267(5) 0.0338(4) Uani 1 1 d . . .
C37 C 0.69704(15) 0.8024(2) 0.28291(5) 0.0401(4) Uani 1 1 d . . .
C41 C 0.76711(11) 0.59960(18) 0.21290(4) 0.0270(3) Uani 1 1 d . . .
C42 C 0.81456(12) 0.5941(2) 0.25139(4) 0.0311(3) Uani 1 1 d . . .
C43 C 0.88455(14) 0.4533(2) 0.26204(5) 0.0400(4) Uani 1 1 d . . .
C44 C 0.90184(14) 0.3214(2) 0.23612(5) 0.0410(4) Uani 1 1 d . . .
C45 C 0.85106(13) 0.3257(2) 0.19869(5) 0.0372(4) Uani 1 1 d . . .
C46 C 0.78384(13) 0.4657(2) 0.18697(5) 0.0322(4) Uani 1 1 d . . .
C47 C 0.79008(15) 0.7223(2) 0.28067(5) 0.0404(4) Uani 1 1 d . . .
H21 H 0.5999(16) 1.013(3) 0.1761(5) 0.053(6) Uiso 1 1 d . . .
H22 H 0.6816(14) 1.083(3) 0.1499(5) 0.046(5) Uiso 1 1 d . . .
H33 H 0.5010(13) 0.815(2) 0.2990(5) 0.044(5) Uiso 1 1 d . . .
H34 H 0.3375(16) 0.780(2) 0.2573(5) 0.055(5) Uiso 1 1 d . . .
H35 H 0.3414(15) 0.734(2) 0.1907(5) 0.046(5) Uiso 1 1 d . . .
H36 H 0.5069(13) 0.707(2) 0.1652(5) 0.041(5) Uiso 1 1 d . . .
H37 H 0.6897(15) 0.873(3) 0.3062(6) 0.057(5) Uiso 1 1 d . . .
H43 H 0.9190(14) 0.450(2) 0.2877(5) 0.049(5) Uiso 1 1 d . . .
H44 H 0.9486(14) 0.232(2) 0.2440(5) 0.046(5) Uiso 1 1 d . . .
H45 H 0.8640(13) 0.233(2) 0.1805(5) 0.042(5) Uiso 1 1 d . . .
H46 H 0.7460(13) 0.473(2) 0.1601(5) 0.042(5) Uiso 1 1 d . . .
H47 H 0.8464(15) 0.735(2) 0.3020(5) 0.049(5) Uiso 1 1 d . . .
N1 N 0.51845(12) 0.4480(2) 0.09537(4) 0.0373(3) Uani 1 1 d . . .
O1 O 0.22881(9) -0.22588(14) 0.11901(4) 0.0407(3) Uani 1 1 d . . .
O2 O 0.11645(8) -0.00689(15) 0.12819(3) 0.0352(3) Uani 1 1 d . . .
O3 O 0.41413(9) -0.15592(14) 0.09966(3) 0.0372(3) Uani 1 1 d . . .
C1 C 0.21025(12) -0.06513(19) 0.11998(4) 0.0280(3) Uani 1 1 d . . .
C2 C 0.28737(11) 0.06907(19) 0.11263(4) 0.0252(3) Uani 1 1 d . . .
C3 C 0.38904(11) 0.01855(18) 0.10331(4) 0.0260(3) Uani 1 1 d . . .
C4 C 0.46477(12) 0.14366(19) 0.09744(4) 0.0274(3) Uani 1 1 d . . .
C5 C 0.44309(11) 0.32473(19) 0.10066(4) 0.0265(3) Uani 1 1 d . . .
C6 C 0.34109(12) 0.3762(2) 0.10914(5) 0.0319(3) Uani 1 1 d . . .
C7 C 0.26688(12) 0.2511(2) 0.11494(4) 0.0304(3) Uani 1 1 d . . .
H1 H 0.5830(15) 0.413(2) 0.0935(5) 0.046(5) Uiso 1 1 d . . .
H2 H 0.0763(16) -0.105(3) 0.1352(6) 0.060(6) Uiso 1 1 d . . .
H3 H 0.3549(17) -0.215(3) 0.1059(6) 0.068(7) Uiso 1 1 d . . .
H4 H 0.5342(13) 0.106(2) 0.0907(5) 0.038(4) Uiso 1 1 d . . .
H6 H 0.3241(13) 0.502(2) 0.1117(5) 0.040(4) Uiso 1 1 d . . .
H7 H 0.1977(13) 0.289(2) 0.1217(5) 0.037(4) Uiso 1 1 d . . .
H10 H 0.5027(14) 0.559(3) 0.0961(5) 0.041(5) Uiso 1 1 d . . .
O4 O 0.00023(10) 0.73072(15) 0.14772(4) 0.0442(3) Uani 1 1 d . . .
C40 C 0.04872(17) 0.5708(3) 0.16213(7) 0.0501(5) Uani 1 1 d . . .
H41 H -0.0620(18) 0.755(3) 0.1565(6) 0.070(7) Uiso 1 1 d . . .
H401 H 0.0080(18) 0.467(3) 0.1504(6) 0.078(7) Uiso 1 1 d . . .
H402 H 0.0461(18) 0.561(3) 0.1899(7) 0.086(8) Uiso 1 1 d . . .
H403 H 0.1197(19) 0.568(3) 0.1546(6) 0.075(7) 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
O11 C10 1.2414(16) . ?
N11 C10 1.3419(19) . ?
N11 H11 0.881(19) . ?
N11 H12 0.909(18) . ?
N12 C10 1.3674(17) . ?
N12 C11 1.4359(18) . ?
N12 C21 1.4376(18) . ?
C11 C16 1.385(2) . ?
C11 C12 1.398(2) . ?
C12 C13 1.401(2) . ?
C12 C17 1.462(2) . ?
C13 C14 1.372(2) . ?
C13 H13 0.969(17) . ?
C14 C15 1.384(2) . ?
C14 H14 0.971(19) . ?
C15 C16 1.379(2) . ?
C15 H15 0.984(17) . ?
C16 H16 0.971(16) . ?
C17 C27 1.337(2) . ?
C17 H17 0.990(19) . ?
C21 C26 1.382(2) . ?
C21 C22 1.397(2) . ?
C22 C23 1.400(2) . ?
C22 C27 1.457(2) . ?
C23 C24 1.376(3) . ?
C23 H23 0.973(18) . ?
C24 C25 1.374(3) . ?
C24 H24 0.965(19) . ?
C25 C26 1.390(2) . ?
C25 H25 0.984(19) . ?
C26 H26 0.964(16) . ?
C27 H27 0.974(18) . ?
O21 C30 1.2461(17) . ?
N21 C30 1.3333(19) . ?
N21 H21 0.89(2) . ?
N21 H22 0.875(19) . ?
N22 C30 1.3678(18) . ?
N22 C41 1.4342(18) . ?
N22 C31 1.4367(18) . ?
C31 C36 1.386(2) . ?
C31 C32 1.396(2) . ?
C32 C33 1.405(2) . ?
C32 C37 1.459(2) . ?
C33 C34 1.373(3) . ?
C33 H33 0.988(17) . ?
C34 C35 1.383(3) . ?
C34 H34 0.973(19) . ?
C35 C36 1.385(2) . ?
C35 H35 0.963(18) . ?
C36 H36 0.976(17) . ?
C37 C47 1.332(2) . ?
C37 H37 0.983(19) . ?
C41 C46 1.383(2) . ?
C41 C42 1.398(2) . ?
C42 C43 1.402(2) . ?
C42 C47 1.460(2) . ?
C43 C44 1.373(3) . ?
C43 H43 0.945(18) . ?
C44 C45 1.379(3) . ?
C44 H44 0.916(18) . ?
C45 C46 1.384(2) . ?
C45 H45 0.968(17) . ?
C46 H46 0.999(17) . ?
C47 H47 0.968(19) . ?
N1 C5 1.3576(19) . ?
N1 H1 0.868(19) . ?
N1 H10 0.859(19) . ?
O1 C1 1.2331(17) . ?
O2 C1 1.3266(17) . ?
O2 H2 0.94(2) . ?
O3 C3 1.3598(17) . ?
O3 H3 0.92(2) . ?
C1 C2 1.447(2) . ?
C2 C7 1.398(2) . ?
C2 C3 1.4143(19) . ?
C3 C4 1.375(2) . ?
C4 C5 1.397(2) . ?
C4 H4 0.977(17) . ?
C5 C6 1.411(2) . ?
C6 C7 1.361(2) . ?
C6 H6 0.978(17) . ?
C7 H7 0.974(17) . ?
O4 C40 1.415(2) . ?
O4 H41 0.90(2) . ?
C40 H401 1.00(2) . ?
C40 H402 0.97(2) . ?
C40 H403 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
C10 N11 H11 123.0(12) . . ?
C10 N11 H12 117.3(11) . . ?
H11 N11 H12 119.4(16) . . ?
C10 N12 C11 119.19(11) . . ?
C10 N12 C21 122.25(11) . . ?
C11 N12 C21 117.11(11) . . ?
O11 C10 N11 121.81(13) . . ?
O11 C10 N12 120.88(12) . . ?
N11 C10 N12 117.30(13) . . ?
C16 C11 C12 121.03(13) . . ?
C16 C11 N12 119.60(13) . . ?
C12 C11 N12 119.37(12) . . ?
C11 C12 C13 117.40(14) . . ?
C11 C12 C17 122.50(13) . . ?
C13 C12 C17 120.10(14) . . ?
C14 C13 C12 121.43(15) . . ?
C14 C13 H13 120.8(10) . . ?
C12 C13 H13 117.8(10) . . ?
C13 C14 C15 120.27(15) . . ?
C13 C14 H14 120.5(10) . . ?
C15 C14 H14 119.2(10) . . ?
C16 C15 C14 119.60(15) . . ?
C16 C15 H15 121.1(9) . . ?
C14 C15 H15 119.3(9) . . ?
C15 C16 C11 120.26(15) . . ?
C15 C16 H16 121.1(9) . . ?
C11 C16 H16 118.6(9) . . ?
C27 C17 C12 127.45(16) . . ?
C27 C17 H17 116.0(11) . . ?
C12 C17 H17 116.2(11) . . ?
C26 C21 C22 121.24(14) . . ?
C26 C21 N12 120.16(14) . . ?
C22 C21 N12 118.60(13) . . ?
C21 C22 C23 117.38(15) . . ?
C21 C22 C27 122.62(14) . . ?
C23 C22 C27 119.96(15) . . ?
C24 C23 C22 121.33(17) . . ?
C24 C23 H23 120.9(10) . . ?
C22 C23 H23 117.7(10) . . ?
C25 C24 C23 120.38(16) . . ?
C25 C24 H24 121.4(11) . . ?
C23 C24 H24 118.2(11) . . ?
C24 C25 C26 119.74(17) . . ?
C24 C25 H25 122.0(11) . . ?
C26 C25 H25 118.3(11) . . ?
C21 C26 C25 119.85(17) . . ?
C21 C26 H26 119.5(9) . . ?
C25 C26 H26 120.6(9) . . ?
C17 C27 C22 127.13(16) . . ?
C17 C27 H27 116.2(10) . . ?
C22 C27 H27 116.0(10) . . ?
C30 N21 H21 120.6(12) . . ?
C30 N21 H22 116.2(12) . . ?
H21 N21 H22 123.0(17) . . ?
C30 N22 C41 120.56(12) . . ?
C30 N22 C31 122.74(12) . . ?
C41 N22 C31 116.65(11) . . ?
O21 C30 N21 121.24(13) . . ?
O21 C30 N22 120.95(13) . . ?
N21 C30 N22 117.81(13) . . ?
C36 C31 C32 121.18(14) . . ?
C36 C31 N22 119.97(13) . . ?
C32 C31 N22 118.84(14) . . ?
C31 C32 C33 117.23(15) . . ?
C31 C32 C37 122.88(14) . . ?
C33 C32 C37 119.89(15) . . ?
C34 C33 C32 121.70(16) . . ?
C34 C33 H33 121.4(10) . . ?
C32 C33 H33 116.9(10) . . ?
C33 C34 C35 120.05(16) . . ?
C33 C34 H34 121.3(11) . . ?
C35 C34 H34 118.7(11) . . ?
C34 C35 C36 119.71(17) . . ?
C34 C35 H35 120.6(11) . . ?
C36 C35 H35 119.7(11) . . ?
C35 C36 C31 120.11(16) . . ?
C35 C36 H36 121.7(10) . . ?
C31 C36 H36 118.2(10) . . ?
C47 C37 C32 127.49(16) . . ?
C47 C37 H37 117.7(11) . . ?
C32 C37 H37 114.5(11) . . ?
C46 C41 C42 121.18(14) . . ?
C46 C41 N22 120.04(14) . . ?
C42 C41 N22 118.75(13) . . ?
C41 C42 C43 117.38(14) . . ?
C41 C42 C47 122.83(14) . . ?
C43 C42 C47 119.71(15) . . ?
C44 C43 C42 121.23(17) . . ?
C44 C43 H43 120.3(11) . . ?
C42 C43 H43 118.4(11) . . ?
C43 C44 C45 120.43(16) . . ?
C43 C44 H44 118.9(11) . . ?
C45 C44 H44 120.7(11) . . ?
C44 C45 C46 119.72(16) . . ?
C44 C45 H45 119.9(10) . . ?
C46 C45 H45 120.3(10) . . ?
C41 C46 C45 119.96(16) . . ?
C41 C46 H46 118.1(10) . . ?
C45 C46 H46 121.9(10) . . ?
C37 C47 C42 126.93(16) . . ?
C37 C47 H47 119.0(11) . . ?
C42 C47 H47 113.5(11) . . ?
C5 N1 H1 118.8(12) . . ?
C5 N1 H10 119.4(12) . . ?
H1 N1 H10 121.5(17) . . ?
C1 O2 H2 108.6(12) . . ?
C3 O3 H3 103.8(13) . . ?
O1 C1 O2 120.51(14) . . ?
O1 C1 C2 123.03(13) . . ?
O2 C1 C2 116.46(13) . . ?
C7 C2 C3 117.13(13) . . ?
C7 C2 C1 122.70(13) . . ?
C3 C2 C1 120.17(13) . . ?
O3 C3 C4 118.21(13) . . ?
O3 C3 C2 120.61(13) . . ?
C4 C3 C2 121.18(13) . . ?
C3 C4 C5 120.60(14) . . ?
C3 C4 H4 119.9(10) . . ?
C5 C4 H4 119.4(10) . . ?
N1 C5 C4 120.52(14) . . ?
N1 C5 C6 120.96(14) . . ?
C4 C5 C6 118.52(13) . . ?
C7 C6 C5 120.30(14) . . ?
C7 C6 H6 119.6(10) . . ?
C5 C6 H6 120.1(10) . . ?
C6 C7 C2 122.24(14) . . ?
C6 C7 H7 119.3(10) . . ?
C2 C7 H7 118.4(10) . . ?
C40 O4 H41 114.6(14) . . ?
O4 C40 H401 110.1(13) . . ?
O4 C40 H402 110.7(14) . . ?
H401 C40 H402 105.4(19) . . ?
O4 C40 H403 107.6(13) . . ?
H401 C40 H403 108.8(18) . . ?
H402 C40 H403 114.2(19) . . ?

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
C11 N12 C10 O11 -0.4(2) . . . . ?
C21 N12 C10 O11 -166.20(13) . . . . ?
C11 N12 C10 N11 -179.84(13) . . . . ?
C21 N12 C10 N11 14.3(2) . . . . ?
C10 N12 C11 C16 77.53(17) . . . . ?
C21 N12 C11 C16 -115.91(15) . . . . ?
C10 N12 C11 C12 -102.35(15) . . . . ?
C21 N12 C11 C12 64.21(17) . . . . ?
C16 C11 C12 C13 0.4(2) . . . . ?
N12 C11 C12 C13 -179.72(12) . . . . ?
C16 C11 C12 C17 -179.16(14) . . . . ?
N12 C11 C12 C17 0.7(2) . . . . ?
C11 C12 C13 C14 -0.1(2) . . . . ?
C17 C12 C13 C14 179.45(15) . . . . ?
C12 C13 C14 C15 -0.7(2) . . . . ?
C13 C14 C15 C16 1.2(2) . . . . ?
C14 C15 C16 C11 -0.9(2) . . . . ?
C12 C11 C16 C15 0.1(2) . . . . ?
N12 C11 C16 C15 -179.76(13) . . . . ?
C11 C12 C17 C27 -33.2(2) . . . . ?
C13 C12 C17 C27 147.21(17) . . . . ?
C10 N12 C21 C26 -82.32(18) . . . . ?
C11 N12 C21 C26 111.56(15) . . . . ?
C10 N12 C21 C22 96.78(16) . . . . ?
C11 N12 C21 C22 -69.33(17) . . . . ?
C26 C21 C22 C23 3.4(2) . . . . ?
N12 C21 C22 C23 -175.74(13) . . . . ?
C26 C21 C22 C27 -174.30(15) . . . . ?
N12 C21 C22 C27 6.6(2) . . . . ?
C21 C22 C23 C24 -1.6(2) . . . . ?
C27 C22 C23 C24 176.11(15) . . . . ?
C22 C23 C24 C25 -0.6(2) . . . . ?
C23 C24 C25 C26 1.1(2) . . . . ?
C22 C21 C26 C25 -2.9(2) . . . . ?
N12 C21 C26 C25 176.15(13) . . . . ?
C24 C25 C26 C21 0.7(2) . . . . ?
C12 C17 C27 C22 -2.9(3) . . . . ?
C21 C22 C27 C17 33.1(3) . . . . ?
C23 C22 C27 C17 -144.50(17) . . . . ?
C41 N22 C30 O21 1.7(2) . . . . ?
C31 N22 C30 O21 179.11(13) . . . . ?
C41 N22 C30 N21 -178.17(13) . . . . ?
C31 N22 C30 N21 -0.7(2) . . . . ?
C30 N22 C31 C36 68.22(19) . . . . ?
C41 N22 C31 C36 -114.24(15) . . . . ?
C30 N22 C31 C32 -111.11(16) . . . . ?
C41 N22 C31 C32 66.43(17) . . . . ?
C36 C31 C32 C33 -1.0(2) . . . . ?
N22 C31 C32 C33 178.36(13) . . . . ?
C36 C31 C32 C37 178.61(14) . . . . ?
N22 C31 C32 C37 -2.1(2) . . . . ?
C31 C32 C33 C34 0.4(2) . . . . ?
C37 C32 C33 C34 -179.15(15) . . . . ?
C32 C33 C34 C35 -0.5(2) . . . . ?
C33 C34 C35 C36 1.1(2) . . . . ?
C34 C35 C36 C31 -1.6(2) . . . . ?
C32 C31 C36 C35 1.6(2) . . . . ?
N22 C31 C36 C35 -177.73(13) . . . . ?
C31 C32 C37 C47 -32.9(3) . . . . ?
C33 C32 C37 C47 146.63(18) . . . . ?
C30 N22 C41 C46 -72.61(18) . . . . ?
C31 N22 C41 C46 109.79(15) . . . . ?
C30 N22 C41 C42 108.98(16) . . . . ?
C31 N22 C41 C42 -68.61(17) . . . . ?
C46 C41 C42 C43 3.7(2) . . . . ?
N22 C41 C42 C43 -177.95(13) . . . . ?
C46 C41 C42 C47 -173.25(15) . . . . ?
N22 C41 C42 C47 5.1(2) . . . . ?
C41 C42 C43 C44 -3.0(2) . . . . ?
C47 C42 C43 C44 174.00(16) . . . . ?
C42 C43 C44 C45 0.6(3) . . . . ?
C43 C44 C45 C46 1.2(2) . . . . ?
C42 C41 C46 C45 -1.9(2) . . . . ?
N22 C41 C46 C45 179.71(13) . . . . ?
C44 C45 C46 C41 -0.6(2) . . . . ?
C32 C37 C47 C42 -1.0(3) . . . . ?
C41 C42 C47 C37 32.6(3) . . . . ?
C43 C42 C47 C37 -144.20(18) . . . . ?
O1 C1 C2 C7 -178.02(15) . . . . ?
O2 C1 C2 C7 1.7(2) . . . . ?
O1 C1 C2 C3 0.9(2) . . . . ?
O2 C1 C2 C3 -179.41(13) . . . . ?
C7 C2 C3 O3 -178.50(13) . . . . ?
C1 C2 C3 O3 2.6(2) . . . . ?
C7 C2 C3 C4 1.1(2) . . . . ?
C1 C2 C3 C4 -177.88(13) . . . . ?
O3 C3 C4 C5 179.73(13) . . . . ?
C2 C3 C4 C5 0.2(2) . . . . ?
C3 C4 C5 N1 179.11(14) . . . . ?
C3 C4 C5 C6 -1.5(2) . . . . ?
N1 C5 C6 C7 -179.03(15) . . . . ?
C4 C5 C6 C7 1.6(2) . . . . ?
C5 C6 C7 C2 -0.3(2) . . . . ?
C3 C2 C7 C6 -1.0(2) . . . . ?
C1 C2 C7 C6 177.94(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
O2 H2 O4 0.94(2) 1.66(2) 2.5982(16) 176.7(19) 1_545
O3 H3 O1 0.92(2) 1.71(2) 2.5673(16) 153.9(19) .
N1 H1 O11 0.868(19) 2.17(2) 2.9849(19) 156.0(16) .
N1 H10 O3 0.859(19) 2.430(19) 3.2692(19) 165.7(15) 1_565
N11 H12 O21 0.909(18) 2.077(19) 2.9843(17) 175.2(15) 1_545
N21 H22 O11 0.875(19) 2.07(2) 2.9408(17) 174.7(17) 1_565
O4 H41 O21 0.90(2) 1.78(2) 2.6434(16) 161(2) 1_455

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.034
