# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_C:\Users\JRWang\Desktop\ADI\2013109.CIF

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ADI
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H30 N12 O8'
_chemical_formula_weight         638.62

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           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   5.2426(8)
_cell_length_b                   11.965(2)
_cell_length_c                   12.256(2)
_cell_angle_alpha                75.126(11)
_cell_angle_beta                 87.661(10)
_cell_angle_gamma                83.717(11)
_cell_volume                     738.5(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6169
_cell_measurement_theta_min      4.50
_cell_measurement_theta_max      54.87

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             334
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9945
_exptl_absorpt_correction_T_max  0.9978
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(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 APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10677
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_sigmaI/netI    0.0377
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.72
_diffrn_reflns_theta_max         24.91
_reflns_number_total             2567
_reflns_number_gt                1709
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0538P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       0.0015(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2567
_refine_ls_number_parameters     225
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0741
_refine_ls_R_factor_gt           0.0398
_refine_ls_wR_factor_ref         0.1007
_refine_ls_wR_factor_gt          0.0874
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_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 0.6086(3) 0.46151(12) 0.66522(11) 0.0531(4) Uani 1 1 d . . .
H1 H 0.733(4) 0.4238(19) 0.6213(18) 0.080 Uiso 1 1 d . . .
O2 O 0.8968(3) 0.39007(14) 0.79811(11) 0.0692(5) Uani 1 1 d . . .
N3' N -0.0117(3) 1.03953(15) 0.82285(14) 0.0472(5) Uani 1 1 d . . .
H6 H 0.002(4) 1.0370(18) 0.8934(18) 0.071 Uiso 1 1 d . . .
O4 O 0.1448(2) 0.96181(11) 0.68166(10) 0.0472(4) Uani 1 1 d . . .
N3 N 0.6905(3) 0.09054(14) 0.54365(14) 0.0415(4) Uani 1 1 d . . .
H13 H 0.673(4) 0.0904(16) 0.4711(17) 0.062 Uiso 1 1 d . . .
O6 O 0.5639(2) 0.15534(12) 0.69641(10) 0.0512(4) Uani 1 1 d . . .
N1' N 0.3370(3) 0.89693(13) 0.96735(12) 0.0407(4) Uani 1 1 d . . .
C6 C 0.6932(4) 0.44280(16) 0.76896(15) 0.0410(5) Uani 1 1 d . . .
C7 C 0.5108(3) 0.49492(17) 0.84314(14) 0.0431(5) Uani 1 1 d . . .
H3 H 0.3491 0.4617 0.8461 0.052 Uiso 1 1 calc R . .
H2 H 0.4784 0.5777 0.8091 0.052 Uiso 1 1 calc R . .
C8 C 0.6015(3) 0.47729(17) 0.96262(14) 0.0433(5) Uani 1 1 d . . .
H4 H 0.7541 0.5169 0.9608 0.052 Uiso 1 1 calc R . .
H5 H 0.6477 0.3950 0.9951 0.052 Uiso 1 1 calc R . .
C5' C 0.1524(3) 0.96902(16) 0.78011(15) 0.0363(5) Uani 1 1 d . . .
C1' C 0.3559(3) 0.89856(15) 0.85796(14) 0.0340(4) Uani 1 1 d . . .
C4' C 0.5255(4) 0.83470(16) 1.03208(15) 0.0440(5) Uani 1 1 d . . .
H19 H 0.5201 0.8312 1.1088 0.053 Uiso 1 1 calc R . .
C3' C 0.7289(4) 0.77514(16) 0.98952(15) 0.0450(5) Uani 1 1 d . . .
H7 H 0.8570 0.7335 1.0384 0.054 Uiso 1 1 calc R . .
N2' N 0.7488(3) 0.77504(14) 0.88118(13) 0.0497(4) Uani 1 1 d . . .
C2' C 0.5586(4) 0.83760(17) 0.81673(15) 0.0455(5) Uani 1 1 d . . .
H8 H 0.5632 0.8402 0.7402 0.055 Uiso 1 1 calc R . .
C5 C 0.5343(3) 0.15295(15) 0.59803(14) 0.0362(4) Uani 1 1 d . . .
C1 C 0.3108(3) 0.22477(14) 0.53469(14) 0.0334(4) Uani 1 1 d . . .
N1 N 0.2793(3) 0.22436(13) 0.42717(12) 0.0417(4) Uani 1 1 d . . .
C4 C 0.0776(4) 0.29044(17) 0.37565(15) 0.0472(5) Uani 1 1 d . . .
H18 H 0.0480 0.2918 0.3010 0.057 Uiso 1 1 calc R . .
C3 C -0.0898(4) 0.35719(17) 0.42874(16) 0.0444(5) Uani 1 1 d . . .
H17 H -0.2273 0.4030 0.3887 0.053 Uiso 1 1 calc R . .
N2 N -0.0600(3) 0.35783(13) 0.53562(12) 0.0420(4) Uani 1 1 d . . .
C2 C 0.1414(4) 0.29123(16) 0.58834(15) 0.0408(5) Uani 1 1 d . . .
H16 H 0.1691 0.2893 0.6633 0.049 Uiso 1 1 calc R . .
H9 H 0.839(4) 0.0450(16) 0.5839(16) 0.064(6) Uiso 1 1 d . . .
H10 H -0.169(5) 1.0842(19) 0.7740(18) 0.086(7) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0480(8) 0.0724(10) 0.0384(8) -0.0250(7) -0.0083(6) 0.0257(7)
O2 0.0507(9) 0.1059(13) 0.0477(9) -0.0298(8) -0.0119(7) 0.0347(9)
N3' 0.0456(10) 0.0611(11) 0.0327(9) -0.0159(9) -0.0062(8) 0.0159(9)
O4 0.0451(8) 0.0665(9) 0.0296(7) -0.0177(6) -0.0040(6) 0.0104(7)
N3 0.0364(10) 0.0536(11) 0.0333(9) -0.0158(8) -0.0029(8) 0.0131(8)
O6 0.0467(8) 0.0718(10) 0.0334(8) -0.0201(7) -0.0088(6) 0.0201(7)
N1' 0.0443(10) 0.0489(10) 0.0298(8) -0.0145(7) -0.0029(7) 0.0035(8)
C6 0.0391(12) 0.0478(12) 0.0354(11) -0.0134(9) -0.0035(9) 0.0058(10)
C7 0.0403(11) 0.0521(12) 0.0377(11) -0.0167(9) -0.0009(9) 0.0052(10)
C8 0.0397(11) 0.0525(12) 0.0396(11) -0.0177(9) -0.0001(9) 0.0021(10)
C5' 0.0337(11) 0.0431(11) 0.0316(11) -0.0108(9) 0.0008(8) 0.0020(9)
C1' 0.0368(10) 0.0386(11) 0.0280(10) -0.0118(8) -0.0009(8) -0.0011(9)
C4' 0.0505(12) 0.0522(13) 0.0280(10) -0.0103(9) -0.0086(9) 0.0041(11)
C3' 0.0433(12) 0.0483(13) 0.0395(12) -0.0066(10) -0.0084(9) 0.0040(10)
N2' 0.0477(10) 0.0575(11) 0.0387(10) -0.0108(8) -0.0024(8) 0.0148(9)
C2' 0.0454(12) 0.0575(13) 0.0310(10) -0.0128(9) -0.0040(9) 0.0108(10)
C5 0.0333(10) 0.0437(11) 0.0304(10) -0.0099(9) 0.0007(8) 0.0025(9)
C1 0.0327(10) 0.0369(11) 0.0299(10) -0.0098(8) 0.0001(8) 0.0024(9)
N1 0.0393(9) 0.0535(10) 0.0314(9) -0.0144(7) -0.0035(7) 0.0092(8)
C4 0.0472(12) 0.0616(14) 0.0311(10) -0.0154(10) -0.0082(9) 0.0137(11)
C3 0.0403(11) 0.0526(12) 0.0364(11) -0.0105(9) -0.0056(9) 0.0118(10)
N2 0.0400(9) 0.0475(10) 0.0366(9) -0.0135(7) -0.0033(7) 0.0114(8)
C2 0.0415(11) 0.0477(12) 0.0330(10) -0.0144(9) -0.0019(9) 0.0061(10)

_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 C6 1.320(2) . ?
O1 H1 0.98(2) . ?
O2 C6 1.197(2) . ?
N3' C5' 1.326(2) . ?
N3' H6 0.86(2) . ?
N3' H10 1.05(2) . ?
O4 C5' 1.2341(19) . ?
N3 C5 1.323(2) . ?
N3 H13 0.90(2) . ?
N3 H9 0.97(2) . ?
O6 C5 1.2300(19) . ?
N1' C4' 1.327(2) . ?
N1' C1' 1.336(2) . ?
C6 C7 1.490(2) . ?
C7 C8 1.514(2) . ?
C7 H3 0.9700 . ?
C7 H2 0.9700 . ?
C8 C8 1.522(3) 2_667 ?
C8 H4 0.9700 . ?
C8 H5 0.9700 . ?
C5' C1' 1.494(2) . ?
C1' C2' 1.376(2) . ?
C4' C3' 1.377(2) . ?
C4' H19 0.9300 . ?
C3' N2' 1.328(2) . ?
C3' H7 0.9300 . ?
N2' C2' 1.332(2) . ?
C2' H8 0.9300 . ?
C5 C1 1.492(2) . ?
C1 N1 1.336(2) . ?
C1 C2 1.386(2) . ?
N1 C4 1.326(2) . ?
C4 C3 1.378(2) . ?
C4 H18 0.9300 . ?
C3 N2 1.328(2) . ?
C3 H17 0.9300 . ?
N2 C2 1.332(2) . ?
C2 H16 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
C6 O1 H1 109.2(13) . . ?
C5' N3' H6 117.6(15) . . ?
C5' N3' H10 118.5(12) . . ?
H6 N3' H10 123(2) . . ?
C5 N3 H13 124.3(13) . . ?
C5 N3 H9 117.6(11) . . ?
H13 N3 H9 118.0(17) . . ?
C4' N1' C1' 115.99(15) . . ?
O2 C6 O1 122.43(17) . . ?
O2 C6 C7 124.69(17) . . ?
O1 C6 C7 112.88(16) . . ?
C6 C7 C8 114.77(16) . . ?
C6 C7 H3 108.6 . . ?
C8 C7 H3 108.6 . . ?
C6 C7 H2 108.6 . . ?
C8 C7 H2 108.6 . . ?
H3 C7 H2 107.5 . . ?
C7 C8 C8 112.52(19) . 2_667 ?
C7 C8 H4 109.1 . . ?
C8 C8 H4 109.1 2_667 . ?
C7 C8 H5 109.1 . . ?
C8 C8 H5 109.1 2_667 . ?
H4 C8 H5 107.8 . . ?
O4 C5' N3' 123.26(17) . . ?
O4 C5' C1' 120.71(16) . . ?
N3' C5' C1' 116.02(16) . . ?
N1' C1' C2' 121.19(16) . . ?
N1' C1' C5' 118.63(16) . . ?
C2' C1' C5' 120.18(15) . . ?
N1' C4' C3' 122.24(17) . . ?
N1' C4' H19 118.9 . . ?
C3' C4' H19 118.9 . . ?
N2' C3' C4' 122.39(18) . . ?
N2' C3' H7 118.8 . . ?
C4' C3' H7 118.8 . . ?
C3' N2' C2' 115.02(17) . . ?
N2' C2' C1' 123.15(17) . . ?
N2' C2' H8 118.4 . . ?
C1' C2' H8 118.4 . . ?
O6 C5 N3 123.92(17) . . ?
O6 C5 C1 118.84(16) . . ?
N3 C5 C1 117.24(16) . . ?
N1 C1 C2 121.40(16) . . ?
N1 C1 C5 119.32(15) . . ?
C2 C1 C5 119.29(16) . . ?
C4 N1 C1 116.26(15) . . ?
N1 C4 C3 122.36(17) . . ?
N1 C4 H18 118.8 . . ?
C3 C4 H18 118.8 . . ?
N2 C3 C4 121.69(17) . . ?
N2 C3 H17 119.2 . . ?
C4 C3 H17 119.2 . . ?
C3 N2 C2 116.42(16) . . ?
N2 C2 C1 121.87(17) . . ?
N2 C2 H16 119.1 . . ?
C1 C2 H16 119.1 . . ?

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
O2 C6 C7 C8 0.3(3) . . . . ?
O1 C6 C7 C8 -179.09(16) . . . . ?
C6 C7 C8 C8 -174.9(2) . . . 2_667 ?
C4' N1' C1' C2' 0.8(3) . . . . ?
C4' N1' C1' C5' -178.79(15) . . . . ?
O4 C5' C1' N1' -171.02(16) . . . . ?
N3' C5' C1' N1' 10.2(2) . . . . ?
O4 C5' C1' C2' 9.4(3) . . . . ?
N3' C5' C1' C2' -169.37(17) . . . . ?
C1' N1' C4' C3' 0.0(3) . . . . ?
N1' C4' C3' N2' -0.7(3) . . . . ?
C4' C3' N2' C2' 0.6(3) . . . . ?
C3' N2' C2' C1' 0.2(3) . . . . ?
N1' C1' C2' N2' -0.9(3) . . . . ?
C5' C1' C2' N2' 178.65(17) . . . . ?
O6 C5 C1 N1 178.84(16) . . . . ?
N3 C5 C1 N1 -0.8(2) . . . . ?
O6 C5 C1 C2 -0.6(3) . . . . ?
N3 C5 C1 C2 179.75(16) . . . . ?
C2 C1 N1 C4 -0.2(3) . . . . ?
C5 C1 N1 C4 -179.70(16) . . . . ?
C1 N1 C4 C3 0.7(3) . . . . ?
N1 C4 C3 N2 -0.9(3) . . . . ?
C4 C3 N2 C2 0.5(3) . . . . ?
C3 N2 C2 C1 0.0(3) . . . . ?
N1 C1 C2 N2 -0.1(3) . . . . ?
C5 C1 C2 N2 179.35(16) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        24.91
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.045
_database_code_depnum_ccdc_archive 'CCDC 1005601'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_C:\Users\JRWang\Desktop\SEB\2013092.CIF

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            PZA-SEB
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H28 N6 O6'
_chemical_formula_weight         448.48

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           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   5.0909(4)
_cell_length_b                   5.4368(5)
_cell_length_c                   20.3002(17)
_cell_angle_alpha                88.781(5)
_cell_angle_beta                 83.380(5)
_cell_angle_gamma                86.981(6)
_cell_volume                     557.29(8)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6169
_cell_measurement_theta_min      4.50
_cell_measurement_theta_max      54.87

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             238
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9830
_exptl_absorpt_correction_T_max  0.9939
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(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 APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8078
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_sigmaI/netI    0.0190
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.02
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1951
_reflns_number_gt                1560
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0460P)²+0.1320P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.014(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1951
_refine_ls_number_parameters     155
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0368
_refine_ls_wR_factor_ref         0.1017
_refine_ls_wR_factor_gt          0.0954
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.055
_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 1.2714(3) 0.3122(2) 0.68785(6) 0.0626(4) Uani 1 1 d . . .
O2 O 1.0871(3) 0.6558(2) 0.73269(6) 0.0676(4) Uani 1 1 d . . .
O3 O 0.6283(2) 0.1695(2) 0.06529(6) 0.0550(4) Uani 1 1 d . . .
N1 N 0.1333(2) 0.6435(2) 0.10287(7) 0.0446(4) Uani 1 1 d . . .
N2 N 0.2392(3) 0.2421(3) 0.02349(7) 0.0501(4) Uani 1 1 d D . .
H13 H 0.089(3) 0.320(3) 0.0268(10) 0.075 Uiso 1 1 d D . .
H11 H 0.271(4) 0.123(3) -0.0034(9) 0.075 Uiso 1 1 d D . .
N3 N 0.4359(3) 0.7043(3) 0.20688(7) 0.0480(4) Uani 1 1 d . . .
C1 C 1.1087(3) 0.5097(3) 0.68882(8) 0.0453(4) Uani 1 1 d . . .
C2 C 0.9531(4) 0.5204(3) 0.63079(8) 0.0546(5) Uani 1 1 d . . .
H6 H 0.8193 0.3990 0.6379 0.065 Uiso 1 1 calc R . .
H5 H 1.0711 0.4724 0.5917 0.065 Uiso 1 1 calc R . .
C3 C 0.8178(4) 0.7658(3) 0.61646(8) 0.0508(4) Uani 1 1 d . . .
H3 H 0.9471 0.8917 0.6126 0.061 Uiso 1 1 calc R . .
H2 H 0.6850 0.8079 0.6532 0.061 Uiso 1 1 calc R . .
C4 C 0.6869(4) 0.7632(3) 0.55315(9) 0.0539(5) Uani 1 1 d . . .
H4 H 0.8185 0.7060 0.5176 0.065 Uiso 1 1 calc R . .
H7 H 0.5506 0.6439 0.5588 0.065 Uiso 1 1 calc R . .
C5 C 0.5637(4) 1.0048(3) 0.53172(8) 0.0526(5) Uani 1 1 d . . .
H8 H 0.6992 1.1248 0.5260 0.063 Uiso 1 1 calc R . .
H9 H 0.4306 1.0620 0.5669 0.063 Uiso 1 1 calc R . .
C6 C 0.2307(3) 0.8573(3) 0.19718(8) 0.0482(4) Uani 1 1 d . . .
H10 H 0.1870 0.9884 0.2257 0.058 Uiso 1 1 calc R . .
C7 C 0.0814(3) 0.8258(3) 0.14585(9) 0.0484(4) Uani 1 1 d . . .
H12 H -0.0612 0.9363 0.1410 0.058 Uiso 1 1 calc R . .
C8 C 0.3419(3) 0.4924(3) 0.11203(7) 0.0375(4) Uani 1 1 d . . .
C9 C 0.4140(3) 0.2866(3) 0.06443(7) 0.0394(4) Uani 1 1 d . . .
C10 C 0.4905(3) 0.5219(3) 0.16381(8) 0.0435(4) Uani 1 1 d . . .
H14 H 0.6328 0.4113 0.1688 0.052 Uiso 1 1 calc R . .
H1 H 1.358(4) 0.303(4) 0.7230(10) 0.065 Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0750(9) 0.0643(8) 0.0500(8) -0.0174(6) -0.0263(6) 0.0299(7)
O2 0.0876(10) 0.0613(8) 0.0571(8) -0.0211(7) -0.0329(7) 0.0278(7)
O3 0.0415(6) 0.0643(8) 0.0609(8) -0.0223(6) -0.0172(5) 0.0165(6)
N1 0.0401(7) 0.0447(8) 0.0490(8) 0.0008(6) -0.0107(6) 0.0077(6)
N2 0.0463(8) 0.0537(9) 0.0530(9) -0.0116(7) -0.0208(7) 0.0086(7)
N3 0.0508(8) 0.0492(8) 0.0442(8) -0.0086(6) -0.0108(6) 0.0104(7)
C1 0.0516(10) 0.0445(9) 0.0397(9) -0.0055(7) -0.0089(7) 0.0078(8)
C2 0.0646(11) 0.0527(11) 0.0485(10) -0.0086(8) -0.0199(9) 0.0103(9)
C3 0.0590(10) 0.0498(10) 0.0456(10) -0.0055(8) -0.0179(8) 0.0066(8)
C4 0.0646(11) 0.0523(11) 0.0472(10) -0.0057(8) -0.0202(8) 0.0074(9)
C5 0.0625(11) 0.0508(10) 0.0471(10) -0.0056(8) -0.0204(8) 0.0066(8)
C6 0.0515(10) 0.0425(9) 0.0488(10) -0.0047(7) -0.0034(8) 0.0104(8)
C7 0.0420(9) 0.0444(9) 0.0574(11) 0.0028(8) -0.0070(8) 0.0127(7)
C8 0.0328(8) 0.0407(9) 0.0386(8) 0.0016(7) -0.0048(6) 0.0024(6)
C9 0.0367(8) 0.0444(9) 0.0375(8) -0.0002(7) -0.0075(6) 0.0014(7)
C10 0.0397(8) 0.0471(9) 0.0438(9) -0.0059(7) -0.0105(7) 0.0111(7)

_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 C1 1.3198(19) . ?
O1 H1 0.88(2) . ?
O2 C1 1.1978(19) . ?
O3 C9 1.2358(17) . ?
N1 C7 1.330(2) . ?
N1 C8 1.3355(18) . ?
N2 C9 1.3201(19) . ?
N2 H13 0.852(9) . ?
N2 H11 0.853(9) . ?
N3 C6 1.331(2) . ?
N3 C10 1.333(2) . ?
C1 C2 1.492(2) . ?
C2 C3 1.508(2) . ?
C2 H6 0.9700 . ?
C2 H5 0.9700 . ?
C3 C4 1.515(2) . ?
C3 H3 0.9700 . ?
C3 H2 0.9700 . ?
C4 C5 1.503(2) . ?
C4 H4 0.9700 . ?
C4 H7 0.9700 . ?
C5 C5 1.510(3) 2_676 ?
C5 H8 0.9700 . ?
C5 H9 0.9700 . ?
C6 C7 1.377(2) . ?
C6 H10 0.9300 . ?
C7 H12 0.9300 . ?
C8 C10 1.381(2) . ?
C8 C9 1.497(2) . ?
C10 H14 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
C1 O1 H1 111.6(13) . . ?
C7 N1 C8 115.90(13) . . ?
C9 N2 H13 120.6(14) . . ?
C9 N2 H11 119.3(14) . . ?
H13 N2 H11 119.7(19) . . ?
C6 N3 C10 116.39(14) . . ?
O2 C1 O1 122.79(15) . . ?
O2 C1 C2 125.35(15) . . ?
O1 C1 C2 111.82(14) . . ?
C1 C2 C3 116.24(14) . . ?
C1 C2 H6 108.2 . . ?
C3 C2 H6 108.2 . . ?
C1 C2 H5 108.2 . . ?
C3 C2 H5 108.2 . . ?
H6 C2 H5 107.4 . . ?
C2 C3 C4 111.98(14) . . ?
C2 C3 H3 109.2 . . ?
C4 C3 H3 109.2 . . ?
C2 C3 H2 109.2 . . ?
C4 C3 H2 109.2 . . ?
H3 C3 H2 107.9 . . ?
C5 C4 C3 116.13(14) . . ?
C5 C4 H4 108.3 . . ?
C3 C4 H4 108.3 . . ?
C5 C4 H7 108.3 . . ?
C3 C4 H7 108.3 . . ?
H4 C4 H7 107.4 . . ?
C4 C5 C5 114.63(18) . 2_676 ?
C4 C5 H8 108.6 . . ?
C5 C5 H8 108.6 2_676 . ?
C4 C5 H9 108.6 . . ?
C5 C5 H9 108.6 2_676 . ?
H8 C5 H9 107.6 . . ?
N3 C6 C7 121.52(15) . . ?
N3 C6 H10 119.2 . . ?
C7 C6 H10 119.2 . . ?
N1 C7 C6 122.52(14) . . ?
N1 C7 H12 118.7 . . ?
C6 C7 H12 118.7 . . ?
N1 C8 C10 121.76(14) . . ?
N1 C8 C9 118.46(13) . . ?
C10 C8 C9 119.78(13) . . ?
O3 C9 N2 123.95(14) . . ?
O3 C9 C8 119.50(13) . . ?
N2 C9 C8 116.54(13) . . ?
N3 C10 C8 121.89(14) . . ?
N3 C10 H14 119.1 . . ?
C8 C10 H14 119.1 . . ?

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
O2 C1 C2 C3 18.0(3) . . . . ?
O1 C1 C2 C3 -164.07(16) . . . . ?
C1 C2 C3 C4 174.72(16) . . . . ?
C2 C3 C4 C5 -175.61(16) . . . . ?
C3 C4 C5 C5 179.7(2) . . . 2_676 ?
C10 N3 C6 C7 0.8(2) . . . . ?
C8 N1 C7 C6 -0.6(2) . . . . ?
N3 C6 C7 N1 -0.5(3) . . . . ?
C7 N1 C8 C10 1.2(2) . . . . ?
C7 N1 C8 C9 -178.74(14) . . . . ?
N1 C8 C9 O3 168.47(15) . . . . ?
C10 C8 C9 O3 -11.5(2) . . . . ?
N1 C8 C9 N2 -11.6(2) . . . . ?
C10 C8 C9 N2 168.49(15) . . . . ?
C6 N3 C10 C8 -0.2(2) . . . . ?
N1 C8 C10 N3 -0.9(2) . . . . ?
C9 C8 C10 N3 179.09(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.137
_refine_diff_density_rms         0.030
_database_code_depnum_ccdc_archive 'CCDC 1005602'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_C:\Users\JRWang\Desktop\trans\mo_2014074.CIF

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            4
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H11 N3 O7'
_chemical_formula_weight         297.23

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   5.0630(11)
_cell_length_b                   10.312(3)
_cell_length_c                   12.716(3)
_cell_angle_alpha                92.328(16)
_cell_angle_beta                 101.006(15)
_cell_angle_gamma                92.647(17)
_cell_volume                     650.2(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.523
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             310
_exptl_absorpt_coefficient_mu    0.129
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9684
_exptl_absorpt_correction_T_max  0.9893
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(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 APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9045
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_av_sigmaI/netI    0.0418
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.98
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2270
_reflns_number_gt                1584
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0678P)²+2.5221P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.019(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2270
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1122
_refine_ls_R_factor_gt           0.0816
_refine_ls_wR_factor_ref         0.2609
_refine_ls_wR_factor_gt          0.2465
_refine_ls_goodness_of_fit_ref   1.183
_refine_ls_restrained_S_all      1.183
_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 1.1362(9) 0.8224(4) -0.0033(4) 0.0554(13) Uani 1 1 d . . .
O3 O 0.7925(11) 1.0666(4) 0.5911(4) 0.0597(14) Uani 1 1 d . . .
H3 H 0.8498 1.0820 0.5366 0.090 Uiso 1 1 calc R . .
O7 O 0.8223(10) 0.5151(5) 0.5771(4) 0.0772(18) Uani 1 1 d . . .
H5 H 0.7177 0.4780 0.5265 0.116 Uiso 1 1 calc R . .
O6 O 0.4658(9) 0.6250(5) 0.5861(4) 0.0653(14) Uani 1 1 d . . .
O2 O 0.9521(12) 0.8733(5) 0.5660(4) 0.0726(16) Uani 1 1 d . . .
O5 O 0.4514(10) 0.8617(4) 0.8664(4) 0.0580(13) Uani 1 1 d . . .
H4 H 0.3728 0.8405 0.9144 0.087 Uiso 1 1 calc R . .
O4 O 0.5747(9) 0.6574(4) 0.8737(3) 0.0497(12) Uani 1 1 d . . .
N1 N 1.2377(10) 0.6187(5) 0.0384(4) 0.0460(13) Uani 1 1 d . . .
H1 H 1.3382 0.6119 -0.0088 0.055 Uiso 1 1 calc R . .
H2 H 1.2167 0.5548 0.0779 0.055 Uiso 1 1 calc R . .
C8 C 0.7298(11) 0.7929(5) 0.7487(4) 0.0369(13) Uani 1 1 d . . .
C11 C 0.5781(12) 0.7638(5) 0.8371(5) 0.0383(13) Uani 1 1 d . . .
C3 C 0.6439(14) 0.7413(7) 0.2800(6) 0.0571(18) Uani 1 1 d . . .
H7 H 0.5430 0.7420 0.3339 0.069 Uiso 1 1 calc R . .
N3 N 0.6606(12) 0.8479(6) 0.2266(5) 0.0614(17) Uani 1 1 d . . .
C2 C 0.8125(14) 0.8406(6) 0.1524(5) 0.0514(17) Uani 1 1 d . . .
H6 H 0.8324 0.9127 0.1124 0.062 Uiso 1 1 calc R . .
C1 C 0.9417(11) 0.7300(5) 0.1325(5) 0.0381(13) Uani 1 1 d . . .
C5 C 1.1166(12) 0.7266(5) 0.0500(5) 0.0401(14) Uani 1 1 d . . .
C4 C 0.7669(14) 0.6304(7) 0.2602(6) 0.0562(18) Uani 1 1 d . . .
H8 H 0.7442 0.5583 0.2999 0.067 Uiso 1 1 calc R . .
N2 N 0.9181(11) 0.6226(5) 0.1858(4) 0.0518(14) Uani 1 1 d . . .
C6 C 0.8329(13) 0.9464(6) 0.6147(5) 0.0453(15) Uani 1 1 d . . .
C7 C 0.7128(12) 0.9096(5) 0.7079(5) 0.0416(14) Uani 1 1 d . . .
H9 H 0.6207 0.9716 0.7394 0.050 Uiso 1 1 calc R . .
C9 C 0.8724(12) 0.6809(5) 0.7117(4) 0.0383(13) Uani 1 1 d . . .
H11 H 0.9195 0.6239 0.7704 0.046 Uiso 1 1 calc R . .
H10 H 1.0383 0.7135 0.6921 0.046 Uiso 1 1 calc R . .
C10 C 0.7051(12) 0.6041(5) 0.6174(5) 0.0412(14) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.062(3) 0.048(3) 0.068(3) 0.018(2) 0.034(2) 0.012(2)
O3 0.083(3) 0.045(3) 0.066(3) 0.018(2) 0.045(3) 0.018(2)
O7 0.063(3) 0.090(4) 0.070(3) -0.041(3) -0.004(3) 0.030(3)
O6 0.049(3) 0.075(3) 0.068(3) -0.019(3) 0.003(2) 0.015(2)
O2 0.111(4) 0.054(3) 0.074(3) 0.017(2) 0.063(3) 0.025(3)
O5 0.081(3) 0.046(3) 0.062(3) 0.016(2) 0.045(3) 0.017(2)
O4 0.061(3) 0.042(2) 0.054(3) 0.012(2) 0.028(2) 0.007(2)
N1 0.054(3) 0.040(3) 0.053(3) 0.008(2) 0.027(3) 0.008(2)
C8 0.038(3) 0.038(3) 0.035(3) -0.002(2) 0.008(2) 0.000(2)
C11 0.044(3) 0.033(3) 0.040(3) 0.006(3) 0.010(3) 0.004(2)
C3 0.058(4) 0.068(5) 0.052(4) 0.007(3) 0.025(3) 0.010(4)
N3 0.075(4) 0.058(4) 0.063(4) 0.008(3) 0.039(3) 0.020(3)
C2 0.068(4) 0.040(3) 0.050(4) 0.007(3) 0.020(3) 0.010(3)
C1 0.036(3) 0.039(3) 0.039(3) 0.004(3) 0.008(3) 0.004(2)
C5 0.048(4) 0.036(3) 0.037(3) 0.003(3) 0.012(3) 0.004(3)
C4 0.061(4) 0.057(4) 0.062(4) 0.019(3) 0.034(4) 0.013(3)
N2 0.057(3) 0.045(3) 0.062(4) 0.018(3) 0.028(3) 0.015(2)
C6 0.055(4) 0.038(3) 0.050(4) 0.007(3) 0.025(3) 0.009(3)
C7 0.052(4) 0.034(3) 0.045(3) 0.003(3) 0.024(3) 0.003(3)
C9 0.045(3) 0.037(3) 0.033(3) 0.005(2) 0.009(3) 0.005(3)
C10 0.044(4) 0.040(3) 0.043(3) 0.003(3) 0.016(3) 0.011(3)

_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 C5 1.232(7) . ?
O3 C6 1.303(7) . ?
O3 H3 0.8200 . ?
O7 C10 1.259(7) . ?
O7 H5 0.8200 . ?
O6 C10 1.233(7) . ?
O2 C6 1.209(7) . ?
O5 C11 1.300(7) . ?
O5 H4 0.8200 . ?
O4 C11 1.209(6) . ?
N1 C5 1.311(7) . ?
N1 H1 0.8600 . ?
N1 H2 0.8600 . ?
C8 C7 1.329(8) . ?
C8 C9 1.497(7) . ?
C8 C11 1.510(8) . ?
C3 N3 1.324(8) . ?
C3 C4 1.364(9) . ?
C3 H7 0.9300 . ?
N3 C2 1.328(8) . ?
C2 C1 1.380(8) . ?
C2 H6 0.9300 . ?
C1 N2 1.334(7) . ?
C1 C5 1.496(8) . ?
C4 N2 1.328(8) . ?
C4 H8 0.9300 . ?
C6 C7 1.486(8) . ?
C7 H9 0.9300 . ?
C9 C10 1.502(8) . ?
C9 H11 0.9700 . ?
C9 H10 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
C6 O3 H3 109.5 . . ?
C10 O7 H5 109.5 . . ?
C11 O5 H4 109.5 . . ?
C5 N1 H1 120.0 . . ?
C5 N1 H2 120.0 . . ?
H1 N1 H2 120.0 . . ?
C7 C8 C9 126.7(5) . . ?
C7 C8 C11 118.5(5) . . ?
C9 C8 C11 114.7(5) . . ?
O4 C11 O5 124.9(5) . . ?
O4 C11 C8 121.5(5) . . ?
O5 C11 C8 113.6(5) . . ?
N3 C3 C4 123.5(6) . . ?
N3 C3 H7 118.2 . . ?
C4 C3 H7 118.2 . . ?
C3 N3 C2 114.8(6) . . ?
N3 C2 C1 122.4(6) . . ?
N3 C2 H6 118.8 . . ?
C1 C2 H6 118.8 . . ?
N2 C1 C2 121.8(5) . . ?
N2 C1 C5 117.4(5) . . ?
C2 C1 C5 120.8(5) . . ?
O1 C5 N1 124.0(5) . . ?
O1 C5 C1 119.2(5) . . ?
N1 C5 C1 116.8(5) . . ?
N2 C4 C3 121.8(6) . . ?
N2 C4 H8 119.1 . . ?
C3 C4 H8 119.1 . . ?
C4 N2 C1 115.6(5) . . ?
O2 C6 O3 124.0(6) . . ?
O2 C6 C7 124.1(5) . . ?
O3 C6 C7 111.9(5) . . ?
C8 C7 C6 123.6(5) . . ?
C8 C7 H9 118.2 . . ?
C6 C7 H9 118.2 . . ?
C8 C9 C10 112.7(5) . . ?
C8 C9 H11 109.1 . . ?
C10 C9 H11 109.1 . . ?
C8 C9 H10 109.1 . . ?
C10 C9 H10 109.1 . . ?
H11 C9 H10 107.8 . . ?
O6 C10 O7 123.4(6) . . ?
O6 C10 C9 121.0(5) . . ?
O7 C10 C9 115.6(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 C8 C11 O4 176.2(6) . . . . ?
C9 C8 C11 O4 -0.1(8) . . . . ?
C7 C8 C11 O5 -2.3(8) . . . . ?
C9 C8 C11 O5 -178.7(5) . . . . ?
C4 C3 N3 C2 -1.3(11) . . . . ?
C3 N3 C2 C1 0.2(10) . . . . ?
N3 C2 C1 N2 1.1(11) . . . . ?
N3 C2 C1 C5 -178.5(6) . . . . ?
N2 C1 C5 O1 177.6(6) . . . . ?
C2 C1 C5 O1 -2.8(9) . . . . ?
N2 C1 C5 N1 -1.4(8) . . . . ?
C2 C1 C5 N1 178.2(6) . . . . ?
N3 C3 C4 N2 1.1(12) . . . . ?
C3 C4 N2 C1 0.2(10) . . . . ?
C2 C1 N2 C4 -1.2(10) . . . . ?
C5 C1 N2 C4 178.3(6) . . . . ?
C9 C8 C7 C6 1.3(10) . . . . ?
C11 C8 C7 C6 -174.6(6) . . . . ?
O2 C6 C7 C8 1.6(11) . . . . ?
O3 C6 C7 C8 -179.0(6) . . . . ?
C7 C8 C9 C10 -82.8(8) . . . . ?
C11 C8 C9 C10 93.2(6) . . . . ?
C8 C9 C10 O6 -8.6(8) . . . . ?
C8 C9 C10 O7 174.4(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.076
_database_code_depnum_ccdc_archive 'CCDC 1005603'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_F:\Paper\PZA\SEB\2013084.CIF

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            PZA-SEB
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H13 N3 O8'
_chemical_formula_weight         315.24

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   5.4495(2)
_cell_length_b                   11.7840(3)
_cell_length_c                   12.0250(4)
_cell_angle_alpha                117.195(2)
_cell_angle_beta                 93.573(2)
_cell_angle_gamma                96.119(2)
_cell_volume                     677.53(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6169
_cell_measurement_theta_min      4.50
_cell_measurement_theta_max      54.87

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.531
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             326
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9749
_exptl_absorpt_correction_T_max  0.9811
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(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 APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9524
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_sigmaI/netI    0.0237
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.92
_diffrn_reflns_theta_max         24.72
_reflns_number_total             2307
_reflns_number_gt                1764
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0361P)²+0.1545P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.012(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2307
_refine_ls_number_parameters     212
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0342
_refine_ls_wR_factor_ref         0.0847
_refine_ls_wR_factor_gt          0.0774
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O8 O -0.0718(2) 1.12725(12) 0.41416(13) 0.0577(4) Uani 1 1 d . . .
O7 O 0.2689(3) 0.00102(13) 0.10532(14) 0.0602(4) Uani 1 1 d . . .
H6 H 0.132(5) -0.050(2) 0.051(2) 0.090 Uiso 1 1 d . . .
O5 O 1.0181(2) 0.61834(12) 0.43896(12) 0.0464(3) Uani 1 1 d . . .
H7 H 1.020(4) 0.708(2) 0.486(2) 0.070 Uiso 1 1 d . . .
O4 O 0.6293(2) 0.62298(12) 0.37349(13) 0.0549(4) Uani 1 1 d . . .
O3 O 0.3411(2) 0.38493(13) 0.33734(12) 0.0458(3) Uani 1 1 d . . .
H8 H 0.320(4) 0.460(2) 0.353(2) 0.069 Uiso 1 1 d . . .
O1 O 0.2518(2) 0.43546(11) 0.14031(11) 0.0478(3) Uani 1 1 d . . .
O2 O 0.5570(2) 0.33083(14) 0.04453(12) 0.0509(4) Uani 1 1 d . . .
H12 H 0.471(4) 0.325(2) -0.025(2) 0.076 Uiso 1 1 d . . .
N1 N 0.2307(3) 0.85191(15) 0.31208(14) 0.0463(4) Uani 1 1 d . . .
N2 N 0.3306(3) 1.11034(16) 0.45036(16) 0.0572(5) Uani 1 1 d . . .
H2 H 0.3693 1.1916 0.5009 0.069 Uiso 1 1 calc R . .
H3 H 0.4427 1.0608 0.4349 0.069 Uiso 1 1 calc R . .
N3 N -0.2230(3) 0.73471(14) 0.16032(14) 0.0454(4) Uani 1 1 d . . .
C1 C -0.0445(4) 0.66710(18) 0.16260(17) 0.0471(5) Uani 1 1 d . . .
H1 H -0.0718 0.5781 0.1121 0.057 Uiso 1 1 calc R . .
C2 C 0.1801(4) 0.72506(19) 0.23760(18) 0.0492(5) Uani 1 1 d . . .
H5 H 0.2999 0.6740 0.2361 0.059 Uiso 1 1 calc R . .
C3 C 0.0498(3) 0.91984(16) 0.31144(15) 0.0381(4) Uani 1 1 d . . .
C5 C 0.1001(3) 1.06193(17) 0.39661(16) 0.0430(5) Uani 1 1 d . . .
C4 C -0.1743(3) 0.86176(18) 0.23604(16) 0.0427(4) Uani 1 1 d . . .
H4 H -0.2951 0.9126 0.2380 0.051 Uiso 1 1 calc R . .
C10 C 0.2817(3) 0.11796(17) 0.11678(17) 0.0440(5) Uani 1 1 d . . .
C9 C 0.5126(3) 0.20538(16) 0.19755(18) 0.0446(5) Uani 1 1 d . . .
H11 H 0.6520 0.1821 0.1494 0.053 Uiso 1 1 calc R . .
H10 H 0.5425 0.1897 0.2694 0.053 Uiso 1 1 calc R . .
C8 C 0.5083(3) 0.34951(16) 0.24631(15) 0.0344(4) Uani 1 1 d . . .
C7 C 0.7730(3) 0.41948(16) 0.30507(16) 0.0385(4) Uani 1 1 d . . .
H14 H 0.8341 0.3887 0.3623 0.046 Uiso 1 1 calc R . .
H13 H 0.8794 0.3968 0.2387 0.046 Uiso 1 1 calc R . .
C6 C 0.7947(3) 0.56262(17) 0.37506(16) 0.0378(4) Uani 1 1 d . . .
O6 O 0.1254(3) 0.14913(12) 0.06447(15) 0.0658(4) Uani 1 1 d . . .
C11 C 0.4210(3) 0.37765(16) 0.13913(15) 0.0355(4) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O8 0.0428(8) 0.0450(8) 0.0647(9) 0.0097(7) -0.0056(7) 0.0066(6)
O7 0.0669(10) 0.0390(8) 0.0684(10) 0.0263(7) -0.0163(8) -0.0092(7)
O5 0.0337(7) 0.0425(7) 0.0494(8) 0.0137(6) -0.0102(6) -0.0039(6)
O4 0.0453(8) 0.0418(8) 0.0611(9) 0.0135(7) -0.0182(7) 0.0046(6)
O3 0.0378(7) 0.0541(8) 0.0445(7) 0.0224(7) 0.0074(6) 0.0042(6)
O1 0.0472(8) 0.0429(8) 0.0471(8) 0.0163(6) -0.0073(6) 0.0114(6)
O2 0.0410(8) 0.0712(9) 0.0357(7) 0.0213(7) 0.0015(6) 0.0084(7)
N1 0.0418(9) 0.0461(10) 0.0480(9) 0.0207(8) -0.0027(7) 0.0048(7)
N2 0.0435(10) 0.0449(10) 0.0607(11) 0.0083(8) -0.0107(8) 0.0032(8)
N3 0.0459(9) 0.0447(10) 0.0378(8) 0.0149(8) -0.0023(7) 0.0001(7)
C1 0.0534(12) 0.0397(11) 0.0438(11) 0.0170(9) 0.0021(9) 0.0032(9)
C2 0.0458(11) 0.0447(12) 0.0553(12) 0.0224(10) -0.0012(10) 0.0083(9)
C3 0.0372(10) 0.0426(11) 0.0334(9) 0.0172(8) 0.0031(8) 0.0046(8)
C5 0.0409(11) 0.0447(11) 0.0384(10) 0.0166(9) -0.0020(8) 0.0032(9)
C4 0.0380(10) 0.0474(12) 0.0399(10) 0.0185(9) 0.0013(8) 0.0065(8)
C10 0.0438(11) 0.0367(11) 0.0478(11) 0.0181(9) 0.0020(9) 0.0013(8)
C9 0.0386(10) 0.0405(11) 0.0514(11) 0.0209(9) -0.0046(9) 0.0019(8)
C8 0.0276(9) 0.0370(10) 0.0354(9) 0.0151(8) -0.0001(7) 0.0027(7)
C7 0.0296(9) 0.0429(11) 0.0381(9) 0.0165(8) -0.0046(8) 0.0021(8)
C6 0.0324(10) 0.0444(11) 0.0332(9) 0.0176(8) -0.0039(8) -0.0012(8)
O6 0.0547(9) 0.0423(8) 0.0902(11) 0.0301(8) -0.0276(8) -0.0091(7)
C11 0.0285(9) 0.0324(9) 0.0354(10) 0.0100(8) -0.0052(8) -0.0030(8)

_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
O8 C5 1.243(2) . ?
O7 C10 1.314(2) . ?
O7 H6 0.91(3) . ?
O5 C6 1.325(2) . ?
O5 H7 0.94(2) . ?
O4 C6 1.211(2) . ?
O3 C8 1.411(2) . ?
O3 H8 0.84(2) . ?
O1 C11 1.200(2) . ?
O2 C11 1.329(2) . ?
O2 H12 0.90(2) . ?
N1 C2 1.331(2) . ?
N1 C3 1.336(2) . ?
N2 C5 1.316(2) . ?
N2 H2 0.8600 . ?
N2 H3 0.8600 . ?
N3 C1 1.328(2) . ?
N3 C4 1.334(2) . ?
C1 C2 1.378(3) . ?
C1 H1 0.9300 . ?
C2 H5 0.9300 . ?
C3 C4 1.378(2) . ?
C3 C5 1.492(2) . ?
C4 H4 0.9300 . ?
C10 O6 1.211(2) . ?
C10 C9 1.498(2) . ?
C9 C8 1.526(2) . ?
C9 H11 0.9700 . ?
C9 H10 0.9700 . ?
C8 C11 1.532(2) . ?
C8 C7 1.532(2) . ?
C7 C6 1.488(2) . ?
C7 H14 0.9700 . ?
C7 H13 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
C10 O7 H6 109.3(16) . . ?
C6 O5 H7 109.7(13) . . ?
C8 O3 H8 105.1(15) . . ?
C11 O2 H12 108.1(14) . . ?
C2 N1 C3 116.18(16) . . ?
C5 N2 H2 120.0 . . ?
C5 N2 H3 120.0 . . ?
H2 N2 H3 120.0 . . ?
C1 N3 C4 116.31(16) . . ?
N3 C1 C2 121.91(18) . . ?
N3 C1 H1 119.0 . . ?
C2 C1 H1 119.0 . . ?
N1 C2 C1 122.00(18) . . ?
N1 C2 H5 119.0 . . ?
C1 C2 H5 119.0 . . ?
N1 C3 C4 121.73(17) . . ?
N1 C3 C5 117.12(15) . . ?
C4 C3 C5 121.15(16) . . ?
O8 C5 N2 123.77(17) . . ?
O8 C5 C3 119.99(16) . . ?
N2 C5 C3 116.24(16) . . ?
N3 C4 C3 121.86(17) . . ?
N3 C4 H4 119.1 . . ?
C3 C4 H4 119.1 . . ?
O6 C10 O7 122.93(17) . . ?
O6 C10 C9 124.43(16) . . ?
O7 C10 C9 112.61(16) . . ?
C10 C9 C8 115.65(15) . . ?
C10 C9 H11 108.4 . . ?
C8 C9 H11 108.4 . . ?
C10 C9 H10 108.4 . . ?
C8 C9 H10 108.4 . . ?
H11 C9 H10 107.4 . . ?
O3 C8 C9 106.50(14) . . ?
O3 C8 C11 110.20(13) . . ?
C9 C8 C11 110.87(14) . . ?
O3 C8 C7 111.34(13) . . ?
C9 C8 C7 107.44(13) . . ?
C11 C8 C7 110.40(13) . . ?
C6 C7 C8 114.45(14) . . ?
C6 C7 H14 108.6 . . ?
C8 C7 H14 108.6 . . ?
C6 C7 H13 108.6 . . ?
C8 C7 H13 108.6 . . ?
H14 C7 H13 107.6 . . ?
O4 C6 O5 122.99(16) . . ?
O4 C6 C7 124.42(15) . . ?
O5 C6 C7 112.57(15) . . ?
O1 C11 O2 123.99(16) . . ?
O1 C11 C8 124.42(16) . . ?
O2 C11 C8 111.59(14) . . ?

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
C4 N3 C1 C2 -0.9(3) . . . . ?
C3 N1 C2 C1 0.9(3) . . . . ?
N3 C1 C2 N1 0.1(3) . . . . ?
C2 N1 C3 C4 -1.2(3) . . . . ?
C2 N1 C3 C5 178.56(16) . . . . ?
N1 C3 C5 O8 -169.43(17) . . . . ?
C4 C3 C5 O8 10.3(3) . . . . ?
N1 C3 C5 N2 9.9(2) . . . . ?
C4 C3 C5 N2 -170.32(17) . . . . ?
C1 N3 C4 C3 0.7(2) . . . . ?
N1 C3 C4 N3 0.4(3) . . . . ?
C5 C3 C4 N3 -179.33(15) . . . . ?
O6 C10 C9 C8 18.6(3) . . . . ?
O7 C10 C9 C8 -163.21(16) . . . . ?
C10 C9 C8 O3 70.81(19) . . . . ?
C10 C9 C8 C11 -49.1(2) . . . . ?
C10 C9 C8 C7 -169.80(15) . . . . ?
O3 C8 C7 C6 -54.75(19) . . . . ?
C9 C8 C7 C6 -171.00(14) . . . . ?
C11 C8 C7 C6 67.99(18) . . . . ?
C8 C7 C6 O4 -9.7(2) . . . . ?
C8 C7 C6 O5 171.12(14) . . . . ?
O3 C8 C11 O1 8.2(2) . . . . ?
C9 C8 C11 O1 125.84(17) . . . . ?
C7 C8 C11 O1 -115.21(18) . . . . ?
O3 C8 C11 O2 -172.25(13) . . . . ?
C9 C8 C11 O2 -54.59(17) . . . . ?
C7 C8 C11 O2 64.36(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        24.72
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.135
_refine_diff_density_rms         0.031
_database_code_depnum_ccdc_archive 'CCDC 1005604'
