# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_ns243
_database_code_depnum_ccdc_archive 'CCDC 1482011'
_audit_update_record             
;
2016-05-26 deposited with the CCDC.
2017-04-07 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT220_ns243               
;
PROBLEM: Non-Solvent Resd 2   O   Ueq(max)/Ueq(min) Range        3.6 Ratio
RESPONSE: Crystal was not of good quality.
;
_vrf_PLAT222_ns243               
;
PROBLEM: Non-Solvent Resd 1   H Uiso(max)/Uiso(min) Range        5.7 Ratio
RESPONSE: Crystal was not of good quality.
;
# Added during the CSD deposition process: Thursday 26 May 2016 08:22 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H15 N O8'
_chemical_formula_sum            'C25 H15 N O8'
_chemical_formula_weight         457.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.9725(6)
_cell_length_b                   13.6991(8)
_cell_length_c                   16.1145(9)
_cell_angle_alpha                76.131(3)
_cell_angle_beta                 74.391(3)
_cell_angle_gamma                84.035(3)
_cell_volume                     2056.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5600
_cell_measurement_theta_min      2.207
_cell_measurement_theta_max      24.999

_exptl_crystal_description       plates
_exptl_crystal_colour            white
_exptl_crystal_size_max          .5
_exptl_crystal_size_mid          .2
_exptl_crystal_size_min          .1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             944
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  .972
_exptl_absorpt_correction_T_max  .987
_exptl_absorpt_process_details   'SADABS; (sheldrick, 2003)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'INCOATEC Imus micro-focus source'
_diffrn_radiation_monochromator  mirrors
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'phi scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            27981
_diffrn_reflns_av_R_equivalents  0.0964
_diffrn_reflns_av_sigmaI/netI    0.1008
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.21
_diffrn_reflns_theta_max         25.00
_reflns_number_total             7173
_reflns_number_gt                3830
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_cell_refinement       'APEX2 (Bruker, 2010); SAINT (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009);XPREP(Sheldrick,2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP (Siemens)'
_computing_publication_material  SHELXL-97

_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)+(0.0332P)²+5.1267P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7173
_refine_ls_number_parameters     617
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1877
_refine_ls_R_factor_gt           0.0989
_refine_ls_wR_factor_ref         0.1874
_refine_ls_wR_factor_gt          0.1657
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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
O1 O -0.2115(3) 0.8370(3) 0.8286(2) 0.0467(9) Uani 1 1 d . . .
O2 O -0.1175(4) 0.6918(3) 0.8821(2) 0.0516(10) Uani 1 1 d . . .
O3 O 0.0792(4) 0.8691(4) 0.5922(2) 0.0744(13) Uani 1 1 d . . .
H3A H 0.1094 0.8144 0.5812 0.06(2) Uiso 1 1 calc R . .
O4 O 0.1747(4) 0.5553(3) 0.5595(2) 0.0589(11) Uani 1 1 d . . .
O5 O 0.2288(4) 0.7077(3) 0.5526(3) 0.0617(11) Uani 1 1 d . . .
O6 O -0.0613(3) 0.5255(3) 0.8142(2) 0.0513(10) Uani 1 1 d . . .
H6B H -0.0697 0.5778 0.8318 0.018(13) Uiso 1 1 calc R . .
O7 O 0.7500(4) 0.6714(4) 0.6583(4) 0.0993(17) Uani 1 1 d . . .
O8 O 0.6192(5) 0.5591(4) 0.6575(4) 0.0955(17) Uani 1 1 d . . .
O9 O 0.0107(3) 0.1620(3) 1.0291(2) 0.0438(9) Uani 1 1 d . . .
O10 O -0.0028(3) 0.3164(3) 0.9528(2) 0.0519(10) Uani 1 1 d . . .
O11 O 0.4160(3) 0.1208(3) 0.8900(2) 0.0514(10) Uani 1 1 d . . .
H11A H 0.4558 0.1741 0.8711 0.11(3) Uiso 1 1 calc R . .
O12 O 0.5633(3) 0.4345(3) 0.8649(2) 0.0480(9) Uani 1 1 d . . .
O13 O 0.5499(3) 0.2866(3) 0.8395(2) 0.0526(10) Uani 1 1 d . . .
O14 O 0.1403(3) 0.4857(3) 0.9170(2) 0.0491(10) Uani 1 1 d . . .
H14B H 0.0996 0.4404 0.9102 0.023(13) Uiso 1 1 calc R . .
O15 O 0.2964(8) 0.1136(6) 0.5366(4) 0.159(3) Uani 1 1 d . . .
O16 O 0.1734(6) 0.0721(4) 0.6680(4) 0.0916(16) Uani 1 1 d . . .
N1 N 0.6358(5) 0.6424(5) 0.6650(3) 0.0681(15) Uani 1 1 d . . .
N2 N 0.2606(7) 0.1233(5) 0.6121(4) 0.0830(18) Uani 1 1 d . . .
C1 C 0.1202(5) 0.6981(4) 0.7399(3) 0.0394(13) Uani 1 1 d . . .
H1A H 0.1063 0.6629 0.8019 0.047 Uiso 1 1 calc R . .
C2 C 0.0021(5) 0.7775(4) 0.7399(3) 0.0388(13) Uani 1 1 d . . .
C3 C -0.0092(5) 0.8553(5) 0.6715(4) 0.0547(16) Uani 1 1 d . . .
C4 C -0.1225(6) 0.9315(4) 0.6808(4) 0.0542(15) Uani 1 1 d . . .
C5 C -0.1382(7) 1.0149(5) 0.6158(4) 0.086(2) Uani 1 1 d . . .
H5A H -0.0740 1.0250 0.5610 0.103 Uiso 1 1 calc R . .
C6 C -0.2477(7) 1.0828(5) 0.6314(4) 0.084(2) Uani 1 1 d . . .
H6A H -0.2579 1.1385 0.5871 0.101 Uiso 1 1 calc R . .
C7 C -0.3416(6) 1.0688(5) 0.7117(4) 0.0670(18) Uani 1 1 d . . .
H7A H -0.4151 1.1156 0.7220 0.080 Uiso 1 1 calc R . .
C8 C -0.3291(5) 0.9873(5) 0.7769(4) 0.0536(15) Uani 1 1 d . . .
H8A H -0.3938 0.9778 0.8315 0.064 Uiso 1 1 calc R . .
C9 C -0.2201(5) 0.9197(4) 0.7611(4) 0.0433(13) Uani 1 1 d . . .
C10 C -0.1080(5) 0.7655(4) 0.8196(4) 0.0424(13) Uani 1 1 d . . .
C11 C 0.1057(5) 0.6179(4) 0.6926(3) 0.0398(13) Uani 1 1 d . . .
C12 C 0.0192(5) 0.5402(4) 0.7318(4) 0.0453(14) Uani 1 1 d . . .
C13 C 0.0096(5) 0.4643(4) 0.6852(4) 0.0493(14) Uani 1 1 d . . .
C14 C -0.0791(6) 0.3851(5) 0.7205(5) 0.0665(18) Uani 1 1 d . . .
H14A H -0.1378 0.3794 0.7770 0.080 Uiso 1 1 calc R . .
C15 C -0.0810(8) 0.3153(5) 0.6732(6) 0.078(2) Uani 1 1 d . . .
H15A H -0.1405 0.2620 0.6975 0.093 Uiso 1 1 calc R . .
C16 C 0.0061(9) 0.3238(6) 0.5884(6) 0.082(2) Uani 1 1 d . . .
H16A H 0.0055 0.2757 0.5564 0.098 Uiso 1 1 calc R . .
C17 C 0.0932(7) 0.4032(6) 0.5518(5) 0.076(2) Uani 1 1 d . . .
H17A H 0.1510 0.4097 0.4951 0.091 Uiso 1 1 calc R . .
C18 C 0.0926(6) 0.4725(4) 0.6009(4) 0.0530(15) Uani 1 1 d . . .
C19 C 0.1714(6) 0.6313(5) 0.5998(4) 0.0506(15) Uani 1 1 d . . .
C20 C 0.2658(5) 0.7392(4) 0.7144(3) 0.0441(13) Uani 1 1 d . . .
C21 C 0.2863(6) 0.8365(5) 0.7158(4) 0.0679(19) Uani 1 1 d . . .
H21A H 0.2093 0.8797 0.7293 0.081 Uiso 1 1 calc R . .
C22 C 0.4171(7) 0.8715(5) 0.6980(5) 0.084(2) Uani 1 1 d . . .
H22A H 0.4271 0.9385 0.6971 0.101 Uiso 1 1 calc R . .
C23 C 0.5336(6) 0.8094(5) 0.6816(4) 0.0707(19) Uani 1 1 d . . .
H23A H 0.6225 0.8324 0.6712 0.085 Uiso 1 1 calc R . .
C24 C 0.5136(5) 0.7124(5) 0.6813(3) 0.0506(15) Uani 1 1 d . . .
C25 C 0.3834(5) 0.6753(4) 0.6984(3) 0.0443(13) Uani 1 1 d . . .
H25A H 0.3741 0.6082 0.6993 0.053 Uiso 1 1 calc R . .
C26 C 0.2604(5) 0.3160(4) 0.8351(3) 0.0368(12) Uani 1 1 d . . .
H26A H 0.1751 0.3554 0.8275 0.044 Uiso 1 1 calc R . .
C27 C 0.2083(5) 0.2250(4) 0.9088(3) 0.0355(12) Uani 1 1 d . . .
C28 C 0.2828(5) 0.1383(4) 0.9304(3) 0.0409(13) Uani 1 1 d . . .
C29 C 0.2178(5) 0.0553(4) 0.9994(3) 0.0383(12) Uani 1 1 d . . .
C30 C 0.2842(5) -0.0387(4) 1.0221(4) 0.0500(14) Uani 1 1 d . . .
H30A H 0.3748 -0.0512 0.9907 0.060 Uiso 1 1 calc R . .
C31 C 0.2182(6) -0.1122(4) 1.0897(4) 0.0568(16) Uani 1 1 d . . .
H31A H 0.2631 -0.1746 1.1040 0.068 Uiso 1 1 calc R . .
C32 C 0.0831(6) -0.0932(4) 1.1370(4) 0.0540(15) Uani 1 1 d . . .
H32A H 0.0389 -0.1431 1.1838 0.065 Uiso 1 1 calc R . .
C33 C 0.0137(6) -0.0025(4) 1.1163(4) 0.0504(15) Uani 1 1 d . . .
H33A H -0.0772 0.0092 1.1477 0.060 Uiso 1 1 calc R . .
C34 C 0.0821(5) 0.0708(4) 1.0475(3) 0.0401(13) Uani 1 1 d . . .
C35 C 0.0682(5) 0.2387(4) 0.9621(3) 0.0397(13) Uani 1 1 d . . .
C36 C 0.3400(5) 0.3852(4) 0.8620(3) 0.0371(12) Uani 1 1 d . . .
C37 C 0.2782(5) 0.4654(4) 0.8953(3) 0.0415(13) Uani 1 1 d . . .
C38 C 0.3587(5) 0.5386(4) 0.9079(3) 0.0404(13) Uani 1 1 d . . .
C39 C 0.3034(6) 0.6276(4) 0.9338(4) 0.0518(15) Uani 1 1 d . . .
H39A H 0.2076 0.6408 0.9473 0.062 Uiso 1 1 calc R . .
C40 C 0.3912(7) 0.6960(5) 0.9394(4) 0.0627(17) Uani 1 1 d . . .
H40A H 0.3548 0.7554 0.9567 0.075 Uiso 1 1 calc R . .
C41 C 0.5334(6) 0.6756(5) 0.9191(4) 0.0587(16) Uani 1 1 d . . .
H41A H 0.5917 0.7224 0.9228 0.070 Uiso 1 1 calc R . .
C42 C 0.5908(6) 0.5902(5) 0.8941(4) 0.0556(16) Uani 1 1 d . . .
H42A H 0.6869 0.5779 0.8805 0.067 Uiso 1 1 calc R . .
C43 C 0.5035(5) 0.5224(4) 0.8892(3) 0.0431(13) Uani 1 1 d . . .
C44 C 0.4867(5) 0.3646(4) 0.8548(3) 0.0419(13) Uani 1 1 d . . .
C45 C 0.3267(5) 0.2918(4) 0.7445(3) 0.0425(13) Uani 1 1 d . . .
C46 C 0.4257(6) 0.3516(5) 0.6808(4) 0.0575(16) Uani 1 1 d . . .
H46A H 0.4584 0.4054 0.6946 0.069 Uiso 1 1 calc R . .
C47 C 0.4767(7) 0.3330(6) 0.5975(4) 0.075(2) Uani 1 1 d . . .
H47A H 0.5464 0.3723 0.5569 0.089 Uiso 1 1 calc R . .
C48 C 0.4267(7) 0.2575(6) 0.5733(4) 0.072(2) Uani 1 1 d . . .
H48A H 0.4599 0.2448 0.5170 0.087 Uiso 1 1 calc R . .
C49 C 0.3253(6) 0.2020(5) 0.6363(4) 0.0554(16) Uani 1 1 d . . .
C50 C 0.2756(5) 0.2158(4) 0.7206(3) 0.0460(14) Uani 1 1 d . . .
H50A H 0.2081 0.1746 0.7612 0.055 Uiso 1 1 calc R . .


_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
O1 C10 1.350(6) . ?
O1 C9 1.383(6) . ?
O2 C10 1.235(6) . ?
O3 C3 1.326(6) . ?
O3 H3A 0.8200 . ?
O4 C19 1.347(6) . ?
O4 C18 1.392(7) . ?
O5 C19 1.228(7) . ?
O6 C12 1.334(6) . ?
O6 H6B 0.8200 . ?
O7 N1 1.215(6) . ?
O8 N1 1.208(6) . ?
O9 C35 1.359(6) . ?
O9 C34 1.380(6) . ?
O10 C35 1.216(6) . ?
O11 C28 1.338(5) . ?
O11 H11A 0.8200 . ?
O12 C44 1.348(6) . ?
O12 C43 1.382(6) . ?
O13 C44 1.227(6) . ?
O14 C37 1.341(5) . ?
O14 H14B 0.8200 . ?
O15 N2 1.207(7) . ?
O16 N2 1.209(7) . ?
N1 C24 1.476(7) . ?
N2 C49 1.487(8) . ?
C1 C11 1.518(7) . ?
C1 C2 1.518(6) . ?
C1 C20 1.528(7) . ?
C1 H1A 0.9800 . ?
C2 C3 1.357(7) . ?
C2 C10 1.435(7) . ?
C3 C4 1.459(7) . ?
C4 C9 1.379(7) . ?
C4 C5 1.379(8) . ?
C5 C6 1.369(8) . ?
C5 H5A 0.9300 . ?
C6 C7 1.361(8) . ?
C6 H6A 0.9300 . ?
C7 C8 1.359(8) . ?
C7 H7A 0.9300 . ?
C8 C9 1.364(7) . ?
C8 H8A 0.9300 . ?
C11 C12 1.361(7) . ?
C11 C19 1.437(8) . ?
C12 C13 1.445(7) . ?
C13 C18 1.374(8) . ?
C13 C14 1.384(8) . ?
C14 C15 1.363(9) . ?
C14 H14A 0.9300 . ?
C15 C16 1.393(10) . ?
C15 H15A 0.9300 . ?
C16 C17 1.378(9) . ?
C16 H16A 0.9300 . ?
C17 C18 1.372(8) . ?
C17 H17A 0.9300 . ?
C20 C21 1.376(7) . ?
C20 C25 1.393(7) . ?
C21 C22 1.369(8) . ?
C21 H21A 0.9300 . ?
C22 C23 1.371(8) . ?
C22 H22A 0.9300 . ?
C23 C24 1.366(8) . ?
C23 H23A 0.9300 . ?
C24 C25 1.378(7) . ?
C25 H25A 0.9300 . ?
C26 C36 1.502(7) . ?
C26 C27 1.525(7) . ?
C26 C45 1.531(7) . ?
C26 H26A 0.9800 . ?
C27 C28 1.357(6) . ?
C27 C35 1.450(6) . ?
C28 C29 1.452(7) . ?
C29 C34 1.391(7) . ?
C29 C30 1.399(7) . ?
C30 C31 1.364(7) . ?
C30 H30A 0.9300 . ?
C31 C32 1.390(7) . ?
C31 H31A 0.9300 . ?
C32 C33 1.372(7) . ?
C32 H32A 0.9300 . ?
C33 C34 1.380(7) . ?
C33 H33A 0.9300 . ?
C36 C37 1.356(7) . ?
C36 C44 1.439(6) . ?
C37 C38 1.429(7) . ?
C38 C39 1.395(7) . ?
C38 C43 1.399(7) . ?
C39 C40 1.381(8) . ?
C39 H39A 0.9300 . ?
C40 C41 1.381(8) . ?
C40 H40A 0.9300 . ?
C41 C42 1.349(8) . ?
C41 H41A 0.9300 . ?
C42 C43 1.366(7) . ?
C42 H42A 0.9300 . ?
C45 C50 1.379(7) . ?
C45 C46 1.385(7) . ?
C46 C47 1.378(8) . ?
C46 H46A 0.9300 . ?
C47 C48 1.369(9) . ?
C47 H47A 0.9300 . ?
C48 C49 1.367(8) . ?
C48 H48A 0.9300 . ?
C49 C50 1.367(7) . ?
C50 H50A 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 O1 C9 122.0(4) . . ?
C3 O3 H3A 109.5 . . ?
C19 O4 C18 121.0(5) . . ?
C12 O6 H6B 109.5 . . ?
C35 O9 C34 121.6(4) . . ?
C28 O11 H11A 109.5 . . ?
C44 O12 C43 122.0(4) . . ?
C37 O14 H14B 109.5 . . ?
O8 N1 O7 122.4(6) . . ?
O8 N1 C24 119.2(5) . . ?
O7 N1 C24 118.5(6) . . ?
O15 N2 O16 122.3(7) . . ?
O15 N2 C49 118.5(7) . . ?
O16 N2 C49 119.2(6) . . ?
C11 C1 C2 112.0(4) . . ?
C11 C1 C20 114.6(4) . . ?
C2 C1 C20 115.0(4) . . ?
C11 C1 H1A 104.6 . . ?
C2 C1 H1A 104.6 . . ?
C20 C1 H1A 104.6 . . ?
C3 C2 C10 118.5(5) . . ?
C3 C2 C1 126.0(5) . . ?
C10 C2 C1 115.5(5) . . ?
O3 C3 C2 124.0(5) . . ?
O3 C3 C4 114.6(5) . . ?
C2 C3 C4 121.4(5) . . ?
C9 C4 C5 117.8(5) . . ?
C9 C4 C3 117.3(5) . . ?
C5 C4 C3 125.0(5) . . ?
C6 C5 C4 120.5(6) . . ?
C6 C5 H5A 119.8 . . ?
C4 C5 H5A 119.8 . . ?
C7 C6 C5 120.1(6) . . ?
C7 C6 H6A 120.0 . . ?
C5 C6 H6A 120.0 . . ?
C8 C7 C6 120.8(6) . . ?
C8 C7 H7A 119.6 . . ?
C6 C7 H7A 119.6 . . ?
C7 C8 C9 119.0(5) . . ?
C7 C8 H8A 120.5 . . ?
C9 C8 H8A 120.5 . . ?
C8 C9 C4 121.9(5) . . ?
C8 C9 O1 117.4(5) . . ?
C4 C9 O1 120.7(5) . . ?
O2 C10 O1 115.9(5) . . ?
O2 C10 C2 124.3(5) . . ?
O1 C10 C2 119.8(5) . . ?
C12 C11 C19 118.3(5) . . ?
C12 C11 C1 122.4(5) . . ?
C19 C11 C1 118.8(5) . . ?
O6 C12 C11 124.9(5) . . ?
O6 C12 C13 114.1(5) . . ?
C11 C12 C13 120.9(5) . . ?
C18 C13 C14 118.7(6) . . ?
C18 C13 C12 117.6(5) . . ?
C14 C13 C12 123.7(6) . . ?
C15 C14 C13 120.5(7) . . ?
C15 C14 H14A 119.8 . . ?
C13 C14 H14A 119.8 . . ?
C14 C15 C16 119.9(7) . . ?
C14 C15 H15A 120.0 . . ?
C16 C15 H15A 120.0 . . ?
C17 C16 C15 120.2(7) . . ?
C17 C16 H16A 119.9 . . ?
C15 C16 H16A 119.9 . . ?
C18 C17 C16 118.6(7) . . ?
C18 C17 H17A 120.7 . . ?
C16 C17 H17A 120.7 . . ?
C17 C18 C13 122.1(6) . . ?
C17 C18 O4 116.9(6) . . ?
C13 C18 O4 120.9(5) . . ?
O5 C19 O4 115.6(5) . . ?
O5 C19 C11 125.0(5) . . ?
O4 C19 C11 119.3(5) . . ?
C21 C20 C25 117.5(5) . . ?
C21 C20 C1 121.9(5) . . ?
C25 C20 C1 120.3(5) . . ?
C22 C21 C20 121.8(6) . . ?
C22 C21 H21A 119.1 . . ?
C20 C21 H21A 119.1 . . ?
C21 C22 C23 121.2(6) . . ?
C21 C22 H22A 119.4 . . ?
C23 C22 H22A 119.4 . . ?
C24 C23 C22 117.1(6) . . ?
C24 C23 H23A 121.4 . . ?
C22 C23 H23A 121.4 . . ?
C23 C24 C25 123.0(5) . . ?
C23 C24 N1 119.2(5) . . ?
C25 C24 N1 117.8(6) . . ?
C24 C25 C20 119.4(5) . . ?
C24 C25 H25A 120.3 . . ?
C20 C25 H25A 120.3 . . ?
C36 C26 C27 113.2(4) . . ?
C36 C26 C45 115.4(4) . . ?
C27 C26 C45 114.7(4) . . ?
C36 C26 H26A 103.9 . . ?
C27 C26 H26A 103.9 . . ?
C45 C26 H26A 103.9 . . ?
C28 C27 C35 119.3(5) . . ?
C28 C27 C26 126.2(4) . . ?
C35 C27 C26 114.4(4) . . ?
O11 C28 C27 124.3(5) . . ?
O11 C28 C29 115.2(5) . . ?
C27 C28 C29 120.5(4) . . ?
C34 C29 C30 117.7(5) . . ?
C34 C29 C28 118.0(5) . . ?
C30 C29 C28 124.2(5) . . ?
C31 C30 C29 121.0(5) . . ?
C31 C30 H30A 119.5 . . ?
C29 C30 H30A 119.5 . . ?
C30 C31 C32 119.5(6) . . ?
C30 C31 H31A 120.3 . . ?
C32 C31 H31A 120.3 . . ?
C33 C32 C31 121.4(5) . . ?
C33 C32 H32A 119.3 . . ?
C31 C32 H32A 119.3 . . ?
C32 C33 C34 118.3(5) . . ?
C32 C33 H33A 120.9 . . ?
C34 C33 H33A 120.9 . . ?
C33 C34 O9 117.1(5) . . ?
C33 C34 C29 122.1(5) . . ?
O9 C34 C29 120.9(5) . . ?
O10 C35 O9 116.2(4) . . ?
O10 C35 C27 124.4(5) . . ?
O9 C35 C27 119.4(5) . . ?
C37 C36 C44 118.3(5) . . ?
C37 C36 C26 122.5(4) . . ?
C44 C36 C26 119.2(4) . . ?
O14 C37 C36 124.8(5) . . ?
O14 C37 C38 113.9(4) . . ?
C36 C37 C38 121.3(4) . . ?
C39 C38 C43 117.4(5) . . ?
C39 C38 C37 124.5(5) . . ?
C43 C38 C37 118.0(5) . . ?
C40 C39 C38 119.9(5) . . ?
C40 C39 H39A 120.0 . . ?
C38 C39 H39A 120.0 . . ?
C39 C40 C41 119.5(5) . . ?
C39 C40 H40A 120.2 . . ?
C41 C40 H40A 120.2 . . ?
C42 C41 C40 122.3(5) . . ?
C42 C41 H41A 118.9 . . ?
C40 C41 H41A 118.9 . . ?
C41 C42 C43 118.0(5) . . ?
C41 C42 H42A 121.0 . . ?
C43 C42 H42A 121.0 . . ?
C42 C43 O12 117.5(5) . . ?
C42 C43 C38 122.8(5) . . ?
O12 C43 C38 119.7(5) . . ?
O13 C44 O12 116.0(4) . . ?
O13 C44 C36 124.5(5) . . ?
O12 C44 C36 119.5(5) . . ?
C50 C45 C46 117.8(5) . . ?
C50 C45 C26 119.6(5) . . ?
C46 C45 C26 122.1(5) . . ?
C47 C46 C45 121.3(6) . . ?
C47 C46 H46A 119.4 . . ?
C45 C46 H46A 119.4 . . ?
C48 C47 C46 121.2(6) . . ?
C48 C47 H47A 119.4 . . ?
C46 C47 H47A 119.4 . . ?
C49 C48 C47 116.4(6) . . ?
C49 C48 H48A 121.8 . . ?
C47 C48 H48A 121.8 . . ?
C50 C49 C48 124.1(6) . . ?
C50 C49 N2 117.0(6) . . ?
C48 C49 N2 118.8(6) . . ?
C49 C50 C45 119.1(5) . . ?
C49 C50 H50A 120.4 . . ?
C45 C50 H50A 120.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 C1 C2 C3 -78.8(7) . . . . ?
C20 C1 C2 C3 54.4(7) . . . . ?
C11 C1 C2 C10 99.2(5) . . . . ?
C20 C1 C2 C10 -127.6(5) . . . . ?
C10 C2 C3 O3 -173.9(5) . . . . ?
C1 C2 C3 O3 4.1(9) . . . . ?
C10 C2 C3 C4 6.4(8) . . . . ?
C1 C2 C3 C4 -175.6(5) . . . . ?
O3 C3 C4 C9 178.3(5) . . . . ?
C2 C3 C4 C9 -2.0(9) . . . . ?
O3 C3 C4 C5 -2.5(9) . . . . ?
C2 C3 C4 C5 177.2(6) . . . . ?
C9 C4 C5 C6 -0.2(11) . . . . ?
C3 C4 C5 C6 -179.3(7) . . . . ?
C4 C5 C6 C7 0.5(12) . . . . ?
C5 C6 C7 C8 -0.6(11) . . . . ?
C6 C7 C8 C9 0.5(10) . . . . ?
C7 C8 C9 C4 -0.2(9) . . . . ?
C7 C8 C9 O1 -179.3(5) . . . . ?
C5 C4 C9 C8 0.0(9) . . . . ?
C3 C4 C9 C8 179.2(5) . . . . ?
C5 C4 C9 O1 179.1(6) . . . . ?
C3 C4 C9 O1 -1.7(8) . . . . ?
C10 O1 C9 C8 179.7(5) . . . . ?
C10 O1 C9 C4 0.6(7) . . . . ?
C9 O1 C10 O2 -174.8(4) . . . . ?
C9 O1 C10 C2 4.1(7) . . . . ?
C3 C2 C10 O2 171.2(5) . . . . ?
C1 C2 C10 O2 -6.9(7) . . . . ?
C3 C2 C10 O1 -7.5(7) . . . . ?
C1 C2 C10 O1 174.4(4) . . . . ?
C2 C1 C11 C12 -80.4(6) . . . . ?
C20 C1 C11 C12 146.2(5) . . . . ?
C2 C1 C11 C19 91.4(5) . . . . ?
C20 C1 C11 C19 -42.0(6) . . . . ?
C19 C11 C12 O6 -171.7(4) . . . . ?
C1 C11 C12 O6 0.1(8) . . . . ?
C19 C11 C12 C13 9.2(7) . . . . ?
C1 C11 C12 C13 -179.0(4) . . . . ?
O6 C12 C13 C18 -178.0(4) . . . . ?
C11 C12 C13 C18 1.2(7) . . . . ?
O6 C12 C13 C14 2.6(7) . . . . ?
C11 C12 C13 C14 -178.2(5) . . . . ?
C18 C13 C14 C15 1.7(8) . . . . ?
C12 C13 C14 C15 -179.0(5) . . . . ?
C13 C14 C15 C16 -0.4(10) . . . . ?
C14 C15 C16 C17 -0.8(10) . . . . ?
C15 C16 C17 C18 0.6(10) . . . . ?
C16 C17 C18 C13 0.8(9) . . . . ?
C16 C17 C18 O4 -175.7(5) . . . . ?
C14 C13 C18 C17 -1.9(8) . . . . ?
C12 C13 C18 C17 178.7(5) . . . . ?
C14 C13 C18 O4 174.5(5) . . . . ?
C12 C13 C18 O4 -4.9(7) . . . . ?
C19 O4 C18 C17 174.2(5) . . . . ?
C19 O4 C18 C13 -2.3(7) . . . . ?
C18 O4 C19 O5 -168.1(5) . . . . ?
C18 O4 C19 C11 13.0(7) . . . . ?
C12 C11 C19 O5 164.9(5) . . . . ?
C1 C11 C19 O5 -7.2(8) . . . . ?
C12 C11 C19 O4 -16.4(7) . . . . ?
C1 C11 C19 O4 171.5(4) . . . . ?
C11 C1 C20 C21 149.4(5) . . . . ?
C2 C1 C20 C21 17.4(8) . . . . ?
C11 C1 C20 C25 -37.9(7) . . . . ?
C2 C1 C20 C25 -169.9(5) . . . . ?
C25 C20 C21 C22 3.2(10) . . . . ?
C1 C20 C21 C22 176.1(6) . . . . ?
C20 C21 C22 C23 -2.8(11) . . . . ?
C21 C22 C23 C24 1.8(11) . . . . ?
C22 C23 C24 C25 -1.4(10) . . . . ?
C22 C23 C24 N1 -179.3(6) . . . . ?
O8 N1 C24 C23 -174.0(6) . . . . ?
O7 N1 C24 C23 5.0(8) . . . . ?
O8 N1 C24 C25 8.0(8) . . . . ?
O7 N1 C24 C25 -173.0(5) . . . . ?
C23 C24 C25 C20 1.9(9) . . . . ?
N1 C24 C25 C20 179.8(5) . . . . ?
C21 C20 C25 C24 -2.7(8) . . . . ?
C1 C20 C25 C24 -175.7(5) . . . . ?
C36 C26 C27 C28 -83.2(6) . . . . ?
C45 C26 C27 C28 52.0(7) . . . . ?
C36 C26 C27 C35 92.8(5) . . . . ?
C45 C26 C27 C35 -132.0(4) . . . . ?
C35 C27 C28 O11 -174.9(5) . . . . ?
C26 C27 C28 O11 1.0(8) . . . . ?
C35 C27 C28 C29 7.4(7) . . . . ?
C26 C27 C28 C29 -176.7(5) . . . . ?
O11 C28 C29 C34 176.2(4) . . . . ?
C27 C28 C29 C34 -5.8(7) . . . . ?
O11 C28 C29 C30 -2.0(7) . . . . ?
C27 C28 C29 C30 175.9(5) . . . . ?
C34 C29 C30 C31 -0.5(8) . . . . ?
C28 C29 C30 C31 177.8(5) . . . . ?
C29 C30 C31 C32 -0.4(9) . . . . ?
C30 C31 C32 C33 1.2(9) . . . . ?
C31 C32 C33 C34 -1.0(8) . . . . ?
C32 C33 C34 O9 -178.8(5) . . . . ?
C32 C33 C34 C29 0.0(8) . . . . ?
C35 O9 C34 C33 -179.3(5) . . . . ?
C35 O9 C34 C29 1.9(7) . . . . ?
C30 C29 C34 C33 0.7(7) . . . . ?
C28 C29 C34 C33 -177.7(5) . . . . ?
C30 C29 C34 O9 179.5(4) . . . . ?
C28 C29 C34 O9 1.1(7) . . . . ?
C34 O9 C35 O10 -178.7(4) . . . . ?
C34 O9 C35 C27 -0.3(7) . . . . ?
C28 C27 C35 O10 173.8(5) . . . . ?
C26 C27 C35 O10 -2.5(7) . . . . ?
C28 C27 C35 O9 -4.4(7) . . . . ?
C26 C27 C35 O9 179.3(4) . . . . ?
C27 C26 C36 C37 -92.6(6) . . . . ?
C45 C26 C36 C37 132.5(5) . . . . ?
C27 C26 C36 C44 85.5(5) . . . . ?
C45 C26 C36 C44 -49.4(6) . . . . ?
C44 C36 C37 O14 -170.4(5) . . . . ?
C26 C36 C37 O14 7.7(8) . . . . ?
C44 C36 C37 C38 11.4(7) . . . . ?
C26 C36 C37 C38 -170.5(5) . . . . ?
O14 C37 C38 C39 -4.7(7) . . . . ?
C36 C37 C38 C39 173.7(5) . . . . ?
O14 C37 C38 C43 178.3(4) . . . . ?
C36 C37 C38 C43 -3.3(7) . . . . ?
C43 C38 C39 C40 0.6(8) . . . . ?
C37 C38 C39 C40 -176.4(5) . . . . ?
C38 C39 C40 C41 0.1(9) . . . . ?
C39 C40 C41 C42 -0.3(9) . . . . ?
C40 C41 C42 C43 -0.1(9) . . . . ?
C41 C42 C43 O12 -179.0(5) . . . . ?
C41 C42 C43 C38 0.8(8) . . . . ?
C44 O12 C43 C42 -177.4(5) . . . . ?
C44 O12 C43 C38 2.8(7) . . . . ?
C39 C38 C43 C42 -1.1(8) . . . . ?
C37 C38 C43 C42 176.1(5) . . . . ?
C39 C38 C43 O12 178.8(5) . . . . ?
C37 C38 C43 O12 -4.0(7) . . . . ?
C43 O12 C44 O13 -174.8(4) . . . . ?
C43 O12 C44 C36 5.5(7) . . . . ?
C37 C36 C44 O13 167.8(5) . . . . ?
C26 C36 C44 O13 -10.4(8) . . . . ?
C37 C36 C44 O12 -12.6(7) . . . . ?
C26 C36 C44 O12 169.2(4) . . . . ?
C36 C26 C45 C50 168.6(4) . . . . ?
C27 C26 C45 C50 34.4(6) . . . . ?
C36 C26 C45 C46 -19.5(7) . . . . ?
C27 C26 C45 C46 -153.7(5) . . . . ?
C50 C45 C46 C47 -3.1(8) . . . . ?
C26 C45 C46 C47 -175.2(5) . . . . ?
C45 C46 C47 C48 3.1(10) . . . . ?
C46 C47 C48 C49 -0.6(10) . . . . ?
C47 C48 C49 C50 -1.8(9) . . . . ?
C47 C48 C49 N2 176.1(6) . . . . ?
O15 N2 C49 C50 175.5(7) . . . . ?
O16 N2 C49 C50 -3.7(9) . . . . ?
O15 N2 C49 C48 -2.6(10) . . . . ?
O16 N2 C49 C48 178.2(6) . . . . ?
C48 C49 C50 C45 1.7(9) . . . . ?
N2 C49 C50 C45 -176.3(5) . . . . ?
C46 C45 C50 C49 0.8(7) . . . . ?
C26 C45 C50 C49 173.1(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.057
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1482010'
_audit_update_record             
;
2016-05-26 deposited with the CCDC.
2017-04-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H10 N2 O4'
_chemical_formula_sum            'C11 H10 N2 O4'
_chemical_formula_weight         234.21

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   9.1088(4)
_cell_length_b                   9.3720(4)
_cell_length_c                   13.9495(5)
_cell_angle_alpha                97.3580(10)
_cell_angle_beta                 92.518(2)
_cell_angle_gamma                118.2320(10)
_cell_volume                     1033.06(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5500
_cell_measurement_theta_min      2.503
_cell_measurement_theta_max      25.999

_exptl_crystal_description       rods
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.512
_exptl_crystal_F_000             488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          .4
_exptl_crystal_size_mid          .2
_exptl_crystal_size_min          .2
_exptl_absorpt_coefficient_mu    0.117
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  .965
_exptl_absorpt_correction_T_max  .971
_exptl_absorpt_process_details   'SADABS; (sheldrick, 2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'INCOATEC Imus micro-focus source'
_diffrn_radiation_monochromator  mirrors
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'phi scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            43386
_diffrn_reflns_av_unetI/netI     0.0110
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.503
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4064
_reflns_number_gt                3495
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_cell_refinement       'APEX2 (Bruker, 2010); SAINT (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009);XPREP(Sheldrick,2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Siemens)'
_computing_publication_material  SHELXL-97
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0644P)²+0.2563P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4064
_refine_ls_number_parameters     326
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0391
_refine_ls_wR_factor_ref         0.1149
_refine_ls_wR_factor_gt          0.1095
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.90808(15) 0.71151(12) 0.01882(8) 0.0490(3) Uani 1 1 d . . . . .
O2 O 0.77682(16) 0.44431(12) -0.04081(7) 0.0513(3) Uani 1 1 d . . . . .
H2A H 0.7750 0.4758 -0.0928 0.077 Uiso 1 1 calc R U . . .
O3 O 0.78818(18) 0.01060(14) 0.29134(8) 0.0569(3) Uani 1 1 d . . . . .
O4 O 0.6611(8) -0.2524(7) 0.2185(6) 0.0557(15) Uani 0.60(3) 1 d . . P A 1
O5 O 0.2375(16) 0.7043(16) 0.2702(9) 0.0563(17) Uani 0.60(3) 1 d . . P A 1
O4A O 0.722(5) -0.230(3) 0.2231(10) 0.100(5) Uani 0.40(3) 1 d . . P A 2
O5A O 0.288(3) 0.734(2) 0.2763(13) 0.059(3) Uani 0.40(3) 1 d . . P A 2
O6 O 0.23529(16) 0.47945(13) 0.20356(7) 0.0460(3) Uani 1 1 d . . . . .
O7 O 0.26187(14) 0.07174(12) 0.54703(7) 0.0447(3) Uani 1 1 d . . . . .
H7A H 0.2474 0.0417 0.6001 0.067 Uiso 1 1 calc R U . . .
O8 O 0.04756(16) -0.17611(14) 0.49382(8) 0.0597(4) Uani 1 1 d . . . . .
N1 N 0.70844(16) 0.09663(14) 0.12423(8) 0.0350(3) Uani 1 1 d . . . . .
N2 N 0.76351(14) 0.35107(13) 0.13237(8) 0.0304(3) Uani 1 1 d . . . . .
N3 N 0.27013(14) 0.16689(13) 0.37211(8) 0.0307(3) Uani 1 1 d . . . . .
N4 N 0.34703(16) 0.42574(14) 0.37289(8) 0.0336(3) Uani 1 1 d . . . . .
C1 C 0.82852(19) 0.25033(18) 0.12807(9) 0.0355(3) Uani 1 1 d . . . . .
H1A H 0.9421 0.2829 0.1278 0.043 Uiso 1 1 calc R U . . .
C2 C 0.55540(18) 0.09605(16) 0.12630(9) 0.0316(3) Uani 1 1 d . . . . .
C3 C 0.3932(2) -0.03009(17) 0.12460(10) 0.0422(4) Uani 1 1 d . . . . .
H3A H 0.3693 -0.1388 0.1216 0.051 Uiso 1 1 calc R U . . .
C4 C 0.2695(2) 0.0146(2) 0.12759(11) 0.0464(4) Uani 1 1 d . . . . .
H4A H 0.1587 -0.0663 0.1265 0.056 Uiso 1 1 calc R U . . .
C5 C 0.30505(19) 0.1782(2) 0.13228(10) 0.0417(4) Uani 1 1 d . . . . .
H5A H 0.2172 0.2025 0.1342 0.050 Uiso 1 1 calc R U . . .
C6 C 0.46595(18) 0.30399(17) 0.13418(9) 0.0343(3) Uani 1 1 d . . . . .
H6A H 0.4897 0.4127 0.1375 0.041 Uiso 1 1 calc R U . . .
C7 C 0.59086(16) 0.25876(15) 0.13091(8) 0.0281(3) Uani 1 1 d . . . . .
C8 C 0.85424(18) 0.52741(16) 0.12975(9) 0.0341(3) Uani 1 1 d . . . . .
H8A H 0.9707 0.5705 0.1554 0.041 Uiso 1 1 calc R U . . .
H8B H 0.8073 0.5818 0.1719 0.041 Uiso 1 1 calc R U . . .
C9 C 0.84724(17) 0.56864(16) 0.02799(10) 0.0328(3) Uani 1 1 d . . . . .
C10 C 0.7303(2) -0.0489(2) 0.11988(10) 0.0471(4) Uani 1 1 d . . . . .
H10A H 0.8356 -0.0256 0.0948 0.057 Uiso 1 1 calc R U . . .
H10B H 0.6407 -0.1385 0.0746 0.057 Uiso 1 1 calc R U . . .
C11 C 0.7303(2) -0.10379(18) 0.21859(10) 0.0396(3) Uani 1 1 d . . . . .
C12 C 0.21806(19) 0.27709(17) 0.37094(9) 0.0345(3) Uani 1 1 d . . . . .
H12A H 0.1065 0.2534 0.3690 0.041 Uiso 1 1 calc R U . . .
C13 C 0.44358(17) 0.24720(15) 0.37501(8) 0.0292(3) Uani 1 1 d . . . . .
C14 C 0.55837(19) 0.18945(17) 0.37586(10) 0.0360(3) Uani 1 1 d . . . . .
H14A H 0.5252 0.0788 0.3747 0.043 Uiso 1 1 calc R U . . .
C15 C 0.7242(2) 0.30509(19) 0.37858(10) 0.0424(4) Uani 1 1 d . . . . .
H15A H 0.8052 0.2714 0.3788 0.051 Uiso 1 1 calc R U . . .
C16 C 0.7748(2) 0.47192(19) 0.38095(11) 0.0438(4) Uani 1 1 d . . . . .
H16A H 0.8885 0.5459 0.3838 0.053 Uiso 1 1 calc R U . . .
C17 C 0.66135(19) 0.52932(17) 0.37919(10) 0.0395(3) Uani 1 1 d . . . . .
H17A H 0.6950 0.6400 0.3803 0.047 Uiso 1 1 calc R U . . .
C18 C 0.49357(18) 0.41317(16) 0.37567(8) 0.0311(3) Uani 1 1 d . . . . .
C19 C 0.3349(2) 0.57602(18) 0.37241(10) 0.0423(4) Uani 1 1 d . . . . .
H19A H 0.4451 0.6697 0.3939 0.051 Uiso 1 1 calc R U . . .
H19B H 0.2609 0.5794 0.4195 0.051 Uiso 1 1 calc R U . . .
C20 C 0.27081(19) 0.59433(17) 0.27453(10) 0.0356(3) Uani 1 1 d . . . . .
C21 C 0.16356(18) -0.00672(16) 0.37754(9) 0.0341(3) Uani 1 1 d . . . . .
H21A H 0.2063 -0.0708 0.3404 0.041 Uiso 1 1 calc R U . . .
H21B H 0.0511 -0.0417 0.3476 0.041 Uiso 1 1 calc R U . . .
C22 C 0.15413(17) -0.04318(16) 0.48121(10) 0.0328(3) 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
O1 C9 1.2101(16) . ?
O2 C9 1.2816(17) . ?
O2 H2A 0.8200 . ?
O3 C11 1.2636(18) . ?
O4 C11 1.227(6) . ?
O5 C20 1.211(12) . ?
O4A C11 1.164(11) . ?
O5A C20 1.235(17) . ?
O6 C20 1.2701(17) . ?
O7 C22 1.2781(17) . ?
O7 H7A 0.8200 . ?
O8 C22 1.2051(17) . ?
N1 C1 1.3261(18) . ?
N1 C2 1.3929(19) . ?
N1 C10 1.4632(17) . ?
N2 C1 1.3279(18) . ?
N2 C7 1.3884(17) . ?
N2 C8 1.4634(16) . ?
N3 C12 1.3262(17) . ?
N3 C13 1.3878(18) . ?
N3 C21 1.4626(16) . ?
N4 C12 1.3270(18) . ?
N4 C18 1.3937(19) . ?
N4 C19 1.4648(17) . ?
C1 H1A 0.9300 . ?
C2 C3 1.385(2) . ?
C2 C7 1.3932(17) . ?
C3 C4 1.376(2) . ?
C3 H3A 0.9300 . ?
C4 C5 1.401(2) . ?
C4 H4A 0.9300 . ?
C5 C6 1.376(2) . ?
C5 H5A 0.9300 . ?
C6 C7 1.3900(19) . ?
C6 H6A 0.9300 . ?
C8 C9 1.5246(18) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C10 C11 1.5304(19) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C12 H12A 0.9300 . ?
C13 C14 1.3865(19) . ?
C13 C18 1.3974(17) . ?
C14 C15 1.376(2) . ?
C14 H14A 0.9300 . ?
C15 C16 1.401(2) . ?
C15 H15A 0.9300 . ?
C16 C17 1.373(2) . ?
C16 H16A 0.9300 . ?
C17 C18 1.389(2) . ?
C17 H17A 0.9300 . ?
C19 C20 1.5229(18) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C21 C22 1.5249(18) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?

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
C9 O2 H2A 109.5 . . ?
C22 O7 H7A 109.5 . . ?
C1 N1 C2 108.36(11) . . ?
C1 N1 C10 126.60(14) . . ?
C2 N1 C10 125.04(13) . . ?
C1 N2 C7 108.53(11) . . ?
C1 N2 C8 126.33(12) . . ?
C7 N2 C8 124.90(11) . . ?
C12 N3 C13 108.29(11) . . ?
C12 N3 C21 125.44(12) . . ?
C13 N3 C21 126.10(11) . . ?
C12 N4 C18 108.30(11) . . ?
C12 N4 C19 125.15(13) . . ?
C18 N4 C19 126.55(12) . . ?
N1 C1 N2 110.32(13) . . ?
N1 C1 H1A 124.8 . . ?
N2 C1 H1A 124.8 . . ?
C3 C2 N1 131.83(13) . . ?
C3 C2 C7 121.77(13) . . ?
N1 C2 C7 106.39(12) . . ?
C4 C3 C2 116.17(13) . . ?
C4 C3 H3A 121.9 . . ?
C2 C3 H3A 121.9 . . ?
C3 C4 C5 122.08(14) . . ?
C3 C4 H4A 119.0 . . ?
C5 C4 H4A 119.0 . . ?
C6 C5 C4 121.99(14) . . ?
C6 C5 H5A 119.0 . . ?
C4 C5 H5A 119.0 . . ?
C5 C6 C7 115.93(13) . . ?
C5 C6 H6A 122.0 . . ?
C7 C6 H6A 122.0 . . ?
N2 C7 C6 131.54(12) . . ?
N2 C7 C2 106.40(11) . . ?
C6 C7 C2 122.06(12) . . ?
N2 C8 C9 113.51(11) . . ?
N2 C8 H8A 108.9 . . ?
C9 C8 H8A 108.9 . . ?
N2 C8 H8B 108.9 . . ?
C9 C8 H8B 108.9 . . ?
H8A C8 H8B 107.7 . . ?
O1 C9 O2 126.20(13) . . ?
O1 C9 C8 118.72(12) . . ?
O2 C9 C8 115.07(11) . . ?
N1 C10 C11 113.44(11) . . ?
N1 C10 H10A 108.9 . . ?
C11 C10 H10A 108.9 . . ?
N1 C10 H10B 108.9 . . ?
C11 C10 H10B 108.9 . . ?
H10A C10 H10B 107.7 . . ?
O4A C11 O3 121.4(10) . . ?
O4 C11 O3 127.8(4) . . ?
O4A C11 C10 120.3(6) . . ?
O4 C11 C10 116.7(4) . . ?
O3 C11 C10 115.09(12) . . ?
N3 C12 N4 110.65(13) . . ?
N3 C12 H12A 124.7 . . ?
N4 C12 H12A 124.7 . . ?
C14 C13 N3 131.56(12) . . ?
C14 C13 C18 121.79(13) . . ?
N3 C13 C18 106.65(12) . . ?
C15 C14 C13 116.21(13) . . ?
C15 C14 H14A 121.9 . . ?
C13 C14 H14A 121.9 . . ?
C14 C15 C16 122.06(14) . . ?
C14 C15 H15A 119.0 . . ?
C16 C15 H15A 119.0 . . ?
C17 C16 C15 121.90(14) . . ?
C17 C16 H16A 119.1 . . ?
C15 C16 H16A 119.1 . . ?
C16 C17 C18 116.39(13) . . ?
C16 C17 H17A 121.8 . . ?
C18 C17 H17A 121.8 . . ?
C17 C18 N4 132.25(12) . . ?
C17 C18 C13 121.64(13) . . ?
N4 C18 C13 106.12(12) . . ?
N4 C19 C20 115.28(11) . . ?
N4 C19 H19A 108.5 . . ?
C20 C19 H19A 108.5 . . ?
N4 C19 H19B 108.5 . . ?
C20 C19 H19B 108.5 . . ?
H19A C19 H19B 107.5 . . ?
O5 C20 O6 123.1(6) . . ?
O5A C20 O6 130.7(8) . . ?
O5 C20 C19 119.4(6) . . ?
O5A C20 C19 111.3(9) . . ?
O6 C20 C19 116.85(12) . . ?
N3 C21 C22 113.59(11) . . ?
N3 C21 H21A 108.8 . . ?
C22 C21 H21A 108.8 . . ?
N3 C21 H21B 108.8 . . ?
C22 C21 H21B 108.8 . . ?
H21A C21 H21B 107.7 . . ?
O8 C22 O7 126.04(13) . . ?
O8 C22 C21 117.78(12) . . ?
O7 C22 C21 116.17(11) . . ?

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
C2 N1 C1 N2 -0.12(14) . . . . ?
C10 N1 C1 N2 -179.35(11) . . . . ?
C7 N2 C1 N1 -0.24(14) . . . . ?
C8 N2 C1 N1 -174.89(11) . . . . ?
C1 N1 C2 C3 -179.55(13) . . . . ?
C10 N1 C2 C3 -0.3(2) . . . . ?
C1 N1 C2 C7 0.42(13) . . . . ?
C10 N1 C2 C7 179.67(11) . . . . ?
N1 C2 C3 C4 -179.95(13) . . . . ?
C7 C2 C3 C4 0.09(19) . . . . ?
C2 C3 C4 C5 -0.1(2) . . . . ?
C3 C4 C5 C6 0.0(2) . . . . ?
C4 C5 C6 C7 0.2(2) . . . . ?
C1 N2 C7 C6 179.76(13) . . . . ?
C8 N2 C7 C6 -5.5(2) . . . . ?
C1 N2 C7 C2 0.49(13) . . . . ?
C8 N2 C7 C2 175.24(11) . . . . ?
C5 C6 C7 N2 -179.37(12) . . . . ?
C5 C6 C7 C2 -0.20(18) . . . . ?
C3 C2 C7 N2 179.43(11) . . . . ?
N1 C2 C7 N2 -0.55(13) . . . . ?
C3 C2 C7 C6 0.07(19) . . . . ?
N1 C2 C7 C6 -179.90(11) . . . . ?
C1 N2 C8 C9 94.12(15) . . . . ?
C7 N2 C8 C9 -79.69(16) . . . . ?
N2 C8 C9 O1 174.79(13) . . . . ?
N2 C8 C9 O2 -5.90(18) . . . . ?
C1 N1 C10 C11 99.11(17) . . . . ?
C2 N1 C10 C11 -80.00(18) . . . . ?
N1 C10 C11 O4A 169(2) . . . . ?
N1 C10 C11 O4 142.3(4) . . . . ?
N1 C10 C11 O3 -31.3(2) . . . . ?
C13 N3 C12 N4 0.00(14) . . . . ?
C21 N3 C12 N4 175.41(11) . . . . ?
C18 N4 C12 N3 -0.09(14) . . . . ?
C19 N4 C12 N3 -179.94(11) . . . . ?
C12 N3 C13 C14 -179.00(13) . . . . ?
C21 N3 C13 C14 5.6(2) . . . . ?
C12 N3 C13 C18 0.09(13) . . . . ?
C21 N3 C13 C18 -175.28(11) . . . . ?
N3 C13 C14 C15 179.73(12) . . . . ?
C18 C13 C14 C15 0.76(19) . . . . ?
C13 C14 C15 C16 0.4(2) . . . . ?
C14 C15 C16 C17 -1.0(2) . . . . ?
C15 C16 C17 C18 0.5(2) . . . . ?
C16 C17 C18 N4 -179.83(13) . . . . ?
C16 C17 C18 C13 0.66(19) . . . . ?
C12 N4 C18 C17 -179.43(13) . . . . ?
C19 N4 C18 C17 0.4(2) . . . . ?
C12 N4 C18 C13 0.14(13) . . . . ?
C19 N4 C18 C13 179.99(11) . . . . ?
C14 C13 C18 C17 -1.32(19) . . . . ?
N3 C13 C18 C17 179.49(11) . . . . ?
C14 C13 C18 N4 179.06(11) . . . . ?
N3 C13 C18 N4 -0.14(13) . . . . ?
C12 N4 C19 C20 -75.38(18) . . . . ?
C18 N4 C19 C20 104.79(16) . . . . ?
N4 C19 C20 O5 171.0(7) . . . . ?
N4 C19 C20 O5A -169.7(13) . . . . ?
N4 C19 C20 O6 -0.3(2) . . . . ?
C12 N3 C21 C22 -92.40(15) . . . . ?
C13 N3 C21 C22 82.20(16) . . . . ?
N3 C21 C22 O8 167.30(14) . . . . ?
N3 C21 C22 O7 -12.89(18) . . . . ?

_refine_diff_density_max         0.253
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.042

