# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 908167'
_audit_update_record             
;
2016-01-25 deposited with the CCDC.
2016-07-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H12 N4, C4 H6 O4'
_chemical_formula_sum            'C10 H18 N4 O4'
_chemical_formula_weight         258.28

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c
_symmetry_space_group_name_Hall  '-P 2ybc'


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

_cell_length_a                   6.0011(3)
_cell_length_b                   18.2772(10)
_cell_length_c                   11.7435(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.398(2)
_cell_angle_gamma                90.00
_cell_volume                     1270.78(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    5060
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      28.30

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             552
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9091
_exptl_absorpt_correction_T_max  0.9792
_exptl_absorpt_process_details   'SADABS (Bruker, 2004)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      295(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 AXS Kappa APEX2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12113
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_sigmaI/netI    0.0185
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.08
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2235
_reflns_number_gt                1801
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Macrae et al., 2008)'
_computing_publication_material  'PLATON (Spek, 2003)'

_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)+(0.0672P)²+0.7824P] 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     SHELXL
_refine_ls_extinction_coef       0.015(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2235
_refine_ls_number_parameters     201
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.0672
_refine_ls_R_factor_gt           0.0554
_refine_ls_wR_factor_ref         0.1568
_refine_ls_wR_factor_gt          0.1447
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.071
_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
C1 C 0.7371(7) 0.5651(2) 0.6032(3) 0.0644(10) Uani 0.868(4) 1 d PD A 1
C2 C 0.8081(7) 0.4943(2) 0.6646(4) 0.0778(13) Uani 0.868(4) 1 d PD A 1
H2A H 0.6940 0.4795 0.7097 0.093 Uiso 0.868(4) 1 calc PR A 1
H2B H 0.8189 0.4564 0.6079 0.093 Uiso 0.868(4) 1 calc PR A 1
C3 C 1.0171(9) 0.5011(2) 0.7377(5) 0.105(2) Uani 0.868(4) 1 d PD A 1
H3A H 1.0013 0.5383 0.7947 0.126 Uiso 0.868(4) 1 calc PR A 1
H3B H 1.1260 0.5192 0.6919 0.126 Uiso 0.868(4) 1 calc PR A 1
C4 C 1.1151(9) 0.4341(2) 0.8007(4) 0.0597(16) Uani 0.868(4) 1 d PD A 1
O1 O 0.5276(5) 0.57883(13) 0.5947(2) 0.0778(9) Uani 0.868(4) 1 d PD A 1
H1 H 0.4997 0.6181 0.5616 0.117 Uiso 0.868(4) 1 calc PR A 1
O2 O 0.8647(5) 0.6050(2) 0.5665(5) 0.141(2) Uani 0.868(4) 1 d PD A 1
O3 O 1.0505(10) 0.3744(2) 0.7811(5) 0.0660(14) Uani 0.868(4) 1 d PD A 1
O4 O 1.2685(8) 0.4509(2) 0.8884(4) 0.112(2) Uani 0.868(4) 1 d PD A 1
H4 H 1.3200 0.4134 0.9207 0.168 Uiso 0.868(4) 1 calc PR A 1
C1' C 0.773(5) 0.5527(14) 0.561(2) 0.0644(10) Uani 0.132(4) 1 d PD A 2
C2' C 0.869(4) 0.4846(13) 0.619(3) 0.0778(13) Uani 0.132(4) 1 d PD A 2
H2'1 H 0.7557 0.4664 0.6624 0.093 Uiso 0.132(4) 1 calc PR A 2
H2'2 H 0.8773 0.4493 0.5584 0.093 Uiso 0.132(4) 1 calc PR A 2
C3' C 1.068(6) 0.4809(15) 0.691(3) 0.105(2) Uani 0.132(4) 1 d PD A 2
H3'1 H 1.0838 0.5273 0.7317 0.126 Uiso 0.132(4) 1 calc PR A 2
H3'2 H 1.1827 0.4804 0.6417 0.126 Uiso 0.132(4) 1 calc PR A 2
C4' C 1.137(7) 0.4236(17) 0.781(4) 0.0597(16) Uani 0.132(4) 1 d PD A 2
O1' O 0.675(4) 0.5968(10) 0.6207(16) 0.0778(9) Uani 0.132(4) 1 d PD A 2
H1' H 0.6357 0.6335 0.5826 0.117 Uiso 0.132(4) 1 calc PR A 2
O2' O 0.786(4) 0.5714(12) 0.468(2) 0.141(2) Uani 0.132(4) 1 d PD A 2
O3' O 1.086(8) 0.3632(16) 0.765(4) 0.089(15) Uani 0.132(4) 1 d PD A 2
O4' O 1.327(3) 0.4396(10) 0.8472(16) 0.044(5) Uani 0.132(4) 1 d PD A 2
H4' H 1.3570 0.4076 0.8964 0.066 Uiso 0.132(4) 1 calc PR A 2
C5 C 0.2027(4) 0.72470(14) 0.4904(2) 0.0562(7) Uani 1 1 d . . .
H5A H 0.1098 0.6863 0.4500 0.067 Uiso 1 1 calc R . .
H5B H 0.1776 0.7250 0.5699 0.067 Uiso 1 1 calc R . .
C6 C 0.5804(4) 0.76760(12) 0.54829(19) 0.0454(6) Uani 1 1 d . . .
H6A H 0.7385 0.7584 0.5451 0.055 Uiso 1 1 calc R . .
H6B H 0.5616 0.7679 0.6288 0.055 Uiso 1 1 calc R . .
C7 C 0.2741(4) 0.85113(14) 0.4994(2) 0.0534(6) Uani 1 1 d . . .
H7A H 0.2499 0.8520 0.5790 0.064 Uiso 1 1 calc R . .
H7B H 0.2291 0.8983 0.4654 0.064 Uiso 1 1 calc R . .
C8 C 0.1746(4) 0.79282(13) 0.31832(19) 0.0466(6) Uani 1 1 d . . .
H8A H 0.0828 0.7546 0.2769 0.056 Uiso 1 1 calc R . .
H8B H 0.1286 0.8391 0.2814 0.056 Uiso 1 1 calc R . .
C9 C 0.4758(4) 0.70951(13) 0.3660(2) 0.0531(6) Uani 1 1 d . . .
H9A H 0.6333 0.6998 0.3623 0.064 Uiso 1 1 calc R . .
H9B H 0.3863 0.6709 0.3242 0.064 Uiso 1 1 calc R . .
C10 C 0.5462(4) 0.83700(13) 0.3741(2) 0.0506(6) Uani 1 1 d . . .
H10A H 0.5032 0.8838 0.3382 0.061 Uiso 1 1 calc R . .
H10B H 0.7044 0.8288 0.3701 0.061 Uiso 1 1 calc R . .
N1 N 0.5161(3) 0.83959(10) 0.49656(15) 0.0442(5) Uani 1 1 d . . .
N2 N 0.1342(3) 0.79470(11) 0.43771(17) 0.0494(5) Uani 1 1 d . . .
N3 N 0.4421(3) 0.70861(10) 0.48747(16) 0.0472(5) Uani 1 1 d . . .
N4 N 0.4118(3) 0.77943(10) 0.31082(15) 0.0453(5) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O2 1.188(5) . ?
C1 O1 1.270(5) . ?
C1 C2 1.509(4) . ?
C2 C3 1.405(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.500(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 O3 1.170(4) . ?
C4 O4 1.301(4) . ?
O1 H1 0.8200 . ?
O4 H4 0.8200 . ?
C1' O2' 1.155(17) . ?
C1' O1' 1.276(17) . ?
C1' C2' 1.490(17) . ?
C2' C3' 1.347(18) . ?
C2' H2'1 0.9700 . ?
C2' H2'2 0.9700 . ?
C3' C4' 1.495(18) . ?
C3' H3'1 0.9700 . ?
C3' H3'2 0.9700 . ?
C4' O3' 1.151(18) . ?
C4' O4' 1.307(18) . ?
O1' H1' 0.8200 . ?
O4' H4' 0.8200 . ?
C5 N2 1.451(3) . ?
C5 N3 1.473(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 N3 1.472(3) . ?
C6 N1 1.474(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 N2 1.448(3) . ?
C7 N1 1.473(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 N4 1.461(3) . ?
C8 N2 1.462(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 N4 1.456(3) . ?
C9 N3 1.473(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 N4 1.454(3) . ?
C10 N1 1.479(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 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
O2 C1 O1 122.6(3) . . ?
O2 C1 C2 123.5(4) . . ?
O1 C1 C2 113.9(3) . . ?
C3 C2 C1 111.7(3) . . ?
C3 C2 H2A 109.3 . . ?
C1 C2 H2A 109.3 . . ?
C3 C2 H2B 109.3 . . ?
C1 C2 H2B 109.3 . . ?
H2A C2 H2B 107.9 . . ?
C2 C3 C4 117.9(3) . . ?
C2 C3 H3A 107.8 . . ?
C4 C3 H3A 107.8 . . ?
C2 C3 H3B 107.8 . . ?
C4 C3 H3B 107.8 . . ?
H3A C3 H3B 107.2 . . ?
O3 C4 O4 123.1(4) . . ?
O3 C4 C3 125.1(4) . . ?
O4 C4 C3 111.6(3) . . ?
C1 O1 H1 109.5 . . ?
C4 O4 H4 109.5 . . ?
O2' C1' O1' 116(2) . . ?
O2' C1' C2' 127(2) . . ?
O1' C1' C2' 117(2) . . ?
C3' C2' C1' 125(2) . . ?
C3' C2' H2'1 106.2 . . ?
C1' C2' H2'1 106.2 . . ?
C3' C2' H2'2 106.2 . . ?
C1' C2' H2'2 106.2 . . ?
H2'1 C2' H2'2 106.4 . . ?
C2' C3' C4' 126(2) . . ?
C2' C3' H3'1 105.8 . . ?
C4' C3' H3'1 105.8 . . ?
C2' C3' H3'2 105.8 . . ?
C4' C3' H3'2 105.8 . . ?
H3'1 C3' H3'2 106.2 . . ?
O3' C4' O4' 119(3) . . ?
O3' C4' C3' 122(3) . . ?
O4' C4' C3' 112(2) . . ?
C1' O1' H1' 109.5 . . ?
C4' O4' H4' 109.5 . . ?
N2 C5 N3 112.06(18) . . ?
N2 C5 H5A 109.2 . . ?
N3 C5 H5A 109.2 . . ?
N2 C5 H5B 109.2 . . ?
N3 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
N3 C6 N1 111.39(16) . . ?
N3 C6 H6A 109.3 . . ?
N1 C6 H6A 109.3 . . ?
N3 C6 H6B 109.3 . . ?
N1 C6 H6B 109.3 . . ?
H6A C6 H6B 108.0 . . ?
N2 C7 N1 112.34(18) . . ?
N2 C7 H7A 109.1 . . ?
N1 C7 H7A 109.1 . . ?
N2 C7 H7B 109.1 . . ?
N1 C7 H7B 109.1 . . ?
H7A C7 H7B 107.9 . . ?
N4 C8 N2 112.19(16) . . ?
N4 C8 H8A 109.2 . . ?
N2 C8 H8A 109.2 . . ?
N4 C8 H8B 109.2 . . ?
N2 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
N4 C9 N3 111.88(17) . . ?
N4 C9 H9A 109.2 . . ?
N3 C9 H9A 109.2 . . ?
N4 C9 H9B 109.2 . . ?
N3 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
N4 C10 N1 111.98(17) . . ?
N4 C10 H10A 109.2 . . ?
N1 C10 H10A 109.2 . . ?
N4 C10 H10B 109.2 . . ?
N1 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
C7 N1 C6 108.15(18) . . ?
C7 N1 C10 107.71(17) . . ?
C6 N1 C10 107.86(17) . . ?
C7 N2 C5 108.30(19) . . ?
C7 N2 C8 108.85(18) . . ?
C5 N2 C8 107.97(18) . . ?
C6 N3 C5 108.49(18) . . ?
C6 N3 C9 107.83(18) . . ?
C5 N3 C9 107.99(18) . . ?
C10 N4 C9 108.89(18) . . ?
C10 N4 C8 108.22(17) . . ?
C9 N4 C8 108.01(18) . . ?

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 39.2(7) . . . . ?
O1 C1 C2 C3 -140.3(5) . . . . ?
C1 C2 C3 C4 -177.3(5) . . . . ?
C2 C3 C4 O3 12.5(10) . . . . ?
C2 C3 C4 O4 -161.3(6) . . . . ?
O2' C1' C2' C3' 96(5) . . . . ?
O1' C1' C2' C3' -80(5) . . . . ?
C1' C2' C3' C4' 158(4) . . . . ?
C2' C3' C4' O3' 37(8) . . . . ?
C2' C3' C4' O4' -171(4) . . . . ?
N2 C7 N1 C6 -58.7(2) . . . . ?
N2 C7 N1 C10 57.6(2) . . . . ?
N3 C6 N1 C7 57.4(2) . . . . ?
N3 C6 N1 C10 -58.9(2) . . . . ?
N4 C10 N1 C7 -58.2(2) . . . . ?
N4 C10 N1 C6 58.3(2) . . . . ?
N1 C7 N2 C5 59.4(2) . . . . ?
N1 C7 N2 C8 -57.8(2) . . . . ?
N3 C5 N2 C7 -59.0(2) . . . . ?
N3 C5 N2 C8 58.7(2) . . . . ?
N4 C8 N2 C7 58.0(2) . . . . ?
N4 C8 N2 C5 -59.3(2) . . . . ?
N1 C6 N3 C5 -57.4(2) . . . . ?
N1 C6 N3 C9 59.3(2) . . . . ?
N2 C5 N3 C6 58.4(2) . . . . ?
N2 C5 N3 C9 -58.2(2) . . . . ?
N4 C9 N3 C6 -59.0(2) . . . . ?
N4 C9 N3 C5 58.0(2) . . . . ?
N1 C10 N4 C9 -58.4(2) . . . . ?
N1 C10 N4 C8 58.8(2) . . . . ?
N3 C9 N4 C10 58.8(2) . . . . ?
N3 C9 N4 C8 -58.5(2) . . . . ?
N2 C8 N4 C10 -58.4(2) . . . . ?
N2 C8 N4 C9 59.3(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O4 H4 N1 0.82 1.85 2.659(4) 169.1 2_746
C8 H8A O3 0.97 2.55 3.465(5) 158.3 3_666
C10 H10B N2 0.97 2.65 3.570(3) 159.3 1_655
C6 H6B N4 0.97 2.60 3.505(3) 155.5 4_576
C7 H7A O3 0.97 2.66 3.502(7) 145.2 2_656
O1 H1 N3 0.82 1.88 2.695(3) 178.7 .

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.467
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.042
####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 908168'
_audit_update_record             
;
2016-01-25 deposited with the CCDC.
2016-07-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H6 O4, C4 H4 O4, 2(C7 H10 N)'
_chemical_formula_sum            'C22 H30 N2 O8'
_chemical_formula_weight         450.48

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           monoclinic
_symmetry_space_group_name_H-M   P21/c
_symmetry_space_group_name_Hall  '-P 2ybc'


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

_cell_length_a                   9.3856(4)
_cell_length_b                   11.0691(6)
_cell_length_c                   21.5537(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.617(3)
_cell_angle_gamma                90.00
_cell_volume                     2236.88(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5865
_cell_measurement_theta_min      2.82
_cell_measurement_theta_max      27.43

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             960
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9100
_exptl_absorpt_correction_T_max  0.9799
_exptl_absorpt_process_details   'SADABS (Bruker, 2004)'

_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 AXS Kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20104
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_sigmaI/netI    0.0223
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.07
_diffrn_reflns_theta_max         25.50
_reflns_number_total             4164
_reflns_number_gt                3384
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Macrae et al., 2008)'
_computing_publication_material  'PLATON (Spek, 2003)'

_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)+(0.0741P)²+1.0521P] 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         4164
_refine_ls_number_parameters     291
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0625
_refine_ls_R_factor_gt           0.0499
_refine_ls_wR_factor_ref         0.1485
_refine_ls_wR_factor_gt          0.1401
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.094
_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
O1A O 0.88394(16) -0.19531(14) 0.44330(8) 0.0455(4) Uani 1 1 d . . .
H1A H 0.9499 -0.2432 0.4490 0.068 Uiso 1 1 calc R . .
O2A O 0.95593(18) -0.13433(15) 0.53701(7) 0.0497(4) Uani 1 1 d . . .
O3A O 0.60257(17) 0.17734(15) 0.48182(7) 0.0439(4) Uani 1 1 d . . .
H3A H 0.5400 0.2290 0.4826 0.066 Uiso 1 1 calc R . .
O4A O 0.57309(19) 0.17567(15) 0.58303(7) 0.0490(4) Uani 1 1 d . . .
C1A C 0.8750(2) -0.12675(18) 0.49179(9) 0.0322(5) Uani 1 1 d . . .
C2A C 0.7570(2) -0.03587(19) 0.48670(11) 0.0377(5) Uani 1 1 d . . .
H2A1 H 0.6675 -0.0782 0.4789 0.045 Uiso 1 1 calc R . .
H2A2 H 0.7719 0.0156 0.4512 0.045 Uiso 1 1 calc R . .
C3A C 0.7444(2) 0.0428(2) 0.54336(10) 0.0396(5) Uani 1 1 d . . .
H3A1 H 0.7244 -0.0084 0.5784 0.047 Uiso 1 1 calc R . .
H3A2 H 0.8355 0.0817 0.5525 0.047 Uiso 1 1 calc R . .
C4A C 0.6311(2) 0.13839(18) 0.53720(10) 0.0326(5) Uani 1 1 d . . .
N1A N 0.35853(19) 0.16614(18) 0.11068(8) 0.0392(4) Uani 1 1 d . . .
H1A1 H 0.2731 0.1813 0.0928 0.059 Uiso 1 1 calc R . .
H1A2 H 0.3831 0.0902 0.1029 0.059 Uiso 1 1 calc R . .
H1A3 H 0.4225 0.2162 0.0955 0.059 Uiso 1 1 calc R . .
C5A C 0.3534(2) 0.1838(2) 0.17779(9) 0.0351(5) Uani 1 1 d . . .
C6A C 0.4382(2) 0.1140(2) 0.21699(10) 0.0386(5) Uani 1 1 d . . .
H6A H 0.4966 0.0553 0.2006 0.046 Uiso 1 1 calc R . .
C7A C 0.4377(3) 0.1300(2) 0.28078(11) 0.0453(6) Uani 1 1 d . . .
C8A C 0.3512(3) 0.2179(3) 0.30299(12) 0.0651(8) Uani 1 1 d . . .
H8A H 0.3496 0.2307 0.3456 0.078 Uiso 1 1 calc R . .
C9A C 0.2671(4) 0.2871(3) 0.26372(14) 0.0778(10) Uani 1 1 d . . .
H9A H 0.2089 0.3459 0.2800 0.093 Uiso 1 1 calc R . .
C10A C 0.2671(3) 0.2710(3) 0.20004(12) 0.0587(7) Uani 1 1 d . . .
H10A H 0.2100 0.3183 0.1733 0.070 Uiso 1 1 calc R . .
C11A C 0.5304(3) 0.0552(3) 0.32337(13) 0.0657(8) Uani 1 1 d . . .
H11A H 0.5841 -0.0005 0.2995 0.099 Uiso 1 1 calc R . .
H11B H 0.4723 0.0111 0.3510 0.099 Uiso 1 1 calc R . .
H11C H 0.5947 0.1067 0.3470 0.099 Uiso 1 1 calc R . .
O1B O 0.40137(15) 0.32136(14) 0.47087(7) 0.0412(4) Uani 1 1 d . . .
O2B O 0.54896(15) 0.43434(14) 0.41907(7) 0.0421(4) Uani 1 1 d . . .
O3B O -0.07663(15) 0.52664(14) 0.41874(7) 0.0404(4) Uani 1 1 d . . .
O4B O 0.08621(15) 0.66037(13) 0.44890(8) 0.0405(4) Uani 1 1 d . . .
C1B C 0.4299(2) 0.41539(18) 0.43984(9) 0.0306(4) Uani 1 1 d . . .
C2B C 0.3136(2) 0.5065(2) 0.42992(12) 0.0430(5) Uani 1 1 d . . .
H2B1 H 0.3257 0.5681 0.4617 0.052 Uiso 1 1 calc R . .
H2B2 H 0.3256 0.5454 0.3902 0.052 Uiso 1 1 calc R . .
C3B C 0.1640(2) 0.45993(19) 0.43088(10) 0.0357(5) Uani 1 1 d . . .
H3B1 H 0.1567 0.4084 0.4670 0.043 Uiso 1 1 calc R . .
H3B2 H 0.1459 0.4100 0.3944 0.043 Uiso 1 1 calc R . .
C4B C 0.0488(2) 0.55456(18) 0.43241(9) 0.0299(4) Uani 1 1 d . . .
N1B N 0.83220(19) 0.29529(18) 0.41062(8) 0.0409(5) Uani 1 1 d . . .
H1B1 H 0.8868 0.2445 0.4332 0.061 Uiso 1 1 calc R . .
H1B2 H 0.7435 0.2928 0.4235 0.061 Uiso 1 1 calc R . .
H1B3 H 0.8664 0.3700 0.4150 0.061 Uiso 1 1 calc R . .
C5B C 0.8322(2) 0.2599(2) 0.34512(10) 0.0353(5) Uani 1 1 d . . .
C6B C 0.9216(2) 0.1695(2) 0.32743(11) 0.0445(6) Uani 1 1 d . . .
H6B H 0.9800 0.1302 0.3570 0.053 Uiso 1 1 calc R . .
C7B C 0.9251(3) 0.1367(2) 0.26538(11) 0.0498(6) Uani 1 1 d . . .
C8B C 0.8377(3) 0.1976(3) 0.22306(11) 0.0565(7) Uani 1 1 d . . .
H8B H 0.8398 0.1776 0.1812 0.068 Uiso 1 1 calc R . .
C9B C 0.7482(3) 0.2866(3) 0.24094(12) 0.0574(7) Uani 1 1 d . . .
H9B H 0.6894 0.3257 0.2114 0.069 Uiso 1 1 calc R . .
C10B C 0.7443(3) 0.3189(2) 0.30253(12) 0.0474(6) Uani 1 1 d . . .
H10B H 0.6832 0.3795 0.3150 0.057 Uiso 1 1 calc R . .
C11B C 1.0240(3) 0.0377(3) 0.24695(16) 0.0784(10) Uani 1 1 d . . .
H11D H 1.0755 0.0075 0.2832 0.118 Uiso 1 1 calc R . .
H11E H 1.0901 0.0689 0.2183 0.118 Uiso 1 1 calc R . .
H11F H 0.9697 -0.0266 0.2276 0.118 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
O1A C1A 1.297(3) . ?
O1A H1A 0.8200 . ?
O2A C1A 1.211(3) . ?
O3A C4A 1.286(3) . ?
O3A H3A 0.8200 . ?
O4A C4A 1.221(2) . ?
C1A C2A 1.497(3) . ?
C2A C3A 1.509(3) . ?
C2A H2A1 0.9700 . ?
C2A H2A2 0.9700 . ?
C3A C4A 1.502(3) . ?
C3A H3A1 0.9700 . ?
C3A H3A2 0.9700 . ?
N1A C5A 1.463(3) . ?
N1A H1A1 0.8900 . ?
N1A H1A2 0.8900 . ?
N1A H1A3 0.8900 . ?
C5A C10A 1.361(3) . ?
C5A C6A 1.373(3) . ?
C6A C7A 1.387(3) . ?
C6A H6A 0.9300 . ?
C7A C8A 1.368(4) . ?
C7A C11A 1.487(4) . ?
C8A C9A 1.366(4) . ?
C8A H8A 0.9300 . ?
C9A C10A 1.384(4) . ?
C9A H9A 0.9300 . ?
C10A H10A 0.9300 . ?
C11A H11A 0.9600 . ?
C11A H11B 0.9600 . ?
C11A H11C 0.9600 . ?
O1B C1B 1.272(2) . ?
O2B C1B 1.240(2) . ?
O3B C4B 1.240(2) . ?
O4B C4B 1.269(3) . ?
C1B C2B 1.495(3) . ?
C2B C3B 1.496(3) . ?
C2B H2B1 0.9700 . ?
C2B H2B2 0.9700 . ?
C3B C4B 1.507(3) . ?
C3B H3B1 0.9700 . ?
C3B H3B2 0.9700 . ?
N1B C5B 1.465(3) . ?
N1B H1B1 0.8900 . ?
N1B H1B2 0.8900 . ?
N1B H1B3 0.8900 . ?
C5B C10B 1.372(3) . ?
C5B C6B 1.371(3) . ?
C6B C7B 1.388(3) . ?
C6B H6B 0.9300 . ?
C7B C8B 1.375(4) . ?
C7B C11B 1.501(4) . ?
C8B C9B 1.362(4) . ?
C8B H8B 0.9300 . ?
C9B C10B 1.377(4) . ?
C9B H9B 0.9300 . ?
C10B H10B 0.9300 . ?
C11B H11D 0.9600 . ?
C11B H11E 0.9600 . ?
C11B H11F 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1A O1A H1A 109.5 . . ?
C4A O3A H3A 109.5 . . ?
O2A C1A O1A 123.14(19) . . ?
O2A C1A C2A 122.72(19) . . ?
O1A C1A C2A 114.14(18) . . ?
C1A C2A C3A 114.43(18) . . ?
C1A C2A H2A1 108.7 . . ?
C3A C2A H2A1 108.7 . . ?
C1A C2A H2A2 108.7 . . ?
C3A C2A H2A2 108.7 . . ?
H2A1 C2A H2A2 107.6 . . ?
C4A C3A C2A 114.61(18) . . ?
C4A C3A H3A1 108.6 . . ?
C2A C3A H3A1 108.6 . . ?
C4A C3A H3A2 108.6 . . ?
C2A C3A H3A2 108.6 . . ?
H3A1 C3A H3A2 107.6 . . ?
O4A C4A O3A 123.78(19) . . ?
O4A C4A C3A 120.44(19) . . ?
O3A C4A C3A 115.78(17) . . ?
C5A N1A H1A1 109.5 . . ?
C5A N1A H1A2 109.5 . . ?
H1A1 N1A H1A2 109.5 . . ?
C5A N1A H1A3 109.5 . . ?
H1A1 N1A H1A3 109.5 . . ?
H1A2 N1A H1A3 109.5 . . ?
C10A C5A C6A 121.3(2) . . ?
C10A C5A N1A 119.4(2) . . ?
C6A C5A N1A 119.28(19) . . ?
C5A C6A C7A 120.7(2) . . ?
C5A C6A H6A 119.7 . . ?
C7A C6A H6A 119.7 . . ?
C8A C7A C6A 117.8(2) . . ?
C8A C7A C11A 121.3(2) . . ?
C6A C7A C11A 120.8(2) . . ?
C9A C8A C7A 121.2(2) . . ?
C9A C8A H8A 119.4 . . ?
C7A C8A H8A 119.4 . . ?
C8A C9A C10A 121.1(3) . . ?
C8A C9A H9A 119.5 . . ?
C10A C9A H9A 119.5 . . ?
C5A C10A C9A 117.9(3) . . ?
C5A C10A H10A 121.1 . . ?
C9A C10A H10A 121.1 . . ?
C7A C11A H11A 109.5 . . ?
C7A C11A H11B 109.5 . . ?
H11A C11A H11B 109.5 . . ?
C7A C11A H11C 109.5 . . ?
H11A C11A H11C 109.5 . . ?
H11B C11A H11C 109.5 . . ?
O2B C1B O1B 122.89(18) . . ?
O2B C1B C2B 119.90(19) . . ?
O1B C1B C2B 117.20(17) . . ?
C3B C2B C1B 116.43(19) . . ?
C3B C2B H2B1 108.2 . . ?
C1B C2B H2B1 108.2 . . ?
C3B C2B H2B2 108.2 . . ?
C1B C2B H2B2 108.2 . . ?
H2B1 C2B H2B2 107.3 . . ?
C2B C3B C4B 115.80(18) . . ?
C2B C3B H3B1 108.3 . . ?
C4B C3B H3B1 108.3 . . ?
C2B C3B H3B2 108.3 . . ?
C4B C3B H3B2 108.3 . . ?
H3B1 C3B H3B2 107.4 . . ?
O3B C4B O4B 122.97(18) . . ?
O3B C4B C3B 119.74(19) . . ?
O4B C4B C3B 117.28(18) . . ?
C5B N1B H1B1 109.5 . . ?
C5B N1B H1B2 109.5 . . ?
H1B1 N1B H1B2 109.5 . . ?
C5B N1B H1B3 109.5 . . ?
H1B1 N1B H1B3 109.5 . . ?
H1B2 N1B H1B3 109.5 . . ?
C10B C5B C6B 121.2(2) . . ?
C10B C5B N1B 119.4(2) . . ?
C6B C5B N1B 119.3(2) . . ?
C5B C6B C7B 120.1(2) . . ?
C5B C6B H6B 120.0 . . ?
C7B C6B H6B 120.0 . . ?
C8B C7B C6B 118.1(2) . . ?
C8B C7B C11B 122.7(2) . . ?
C6B C7B C11B 119.2(3) . . ?
C9B C8B C7B 121.6(2) . . ?
C9B C8B H8B 119.2 . . ?
C7B C8B H8B 119.2 . . ?
C8B C9B C10B 120.3(3) . . ?
C8B C9B H9B 119.8 . . ?
C10B C9B H9B 119.8 . . ?
C5B C10B C9B 118.7(2) . . ?
C5B C10B H10B 120.7 . . ?
C9B C10B H10B 120.7 . . ?
C7B C11B H11D 109.5 . . ?
C7B C11B H11E 109.5 . . ?
H11D C11B H11E 109.5 . . ?
C7B C11B H11F 109.5 . . ?
H11D C11B H11F 109.5 . . ?
H11E C11B H11F 109.5 . . ?

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
O2A C1A C2A C3A -1.8(3) . . . . ?
O1A C1A C2A C3A 179.02(19) . . . . ?
C1A C2A C3A C4A 176.94(18) . . . . ?
C2A C3A C4A O4A 152.1(2) . . . . ?
C2A C3A C4A O3A -28.7(3) . . . . ?
C10A C5A C6A C7A 0.4(3) . . . . ?
N1A C5A C6A C7A 178.81(19) . . . . ?
C5A C6A C7A C8A -0.5(3) . . . . ?
C5A C6A C7A C11A -179.5(2) . . . . ?
C6A C7A C8A C9A 0.5(4) . . . . ?
C11A C7A C8A C9A 179.5(3) . . . . ?
C7A C8A C9A C10A -0.3(5) . . . . ?
C6A C5A C10A C9A -0.2(4) . . . . ?
N1A C5A C10A C9A -178.6(3) . . . . ?
C8A C9A C10A C5A 0.2(5) . . . . ?
O2B C1B C2B C3B 154.8(2) . . . . ?
O1B C1B C2B C3B -26.5(3) . . . . ?
C1B C2B C3B C4B 169.42(18) . . . . ?
C2B C3B C4B O3B 163.1(2) . . . . ?
C2B C3B C4B O4B -18.0(3) . . . . ?
C10B C5B C6B C7B 0.5(4) . . . . ?
N1B C5B C6B C7B -178.6(2) . . . . ?
C5B C6B C7B C8B 0.4(4) . . . . ?
C5B C6B C7B C11B 179.8(2) . . . . ?
C6B C7B C8B C9B -1.0(4) . . . . ?
C11B C7B C8B C9B 179.6(3) . . . . ?
C7B C8B C9B C10B 0.8(4) . . . . ?
C6B C5B C10B C9B -0.7(4) . . . . ?
N1B C5B C10B C9B 178.4(2) . . . . ?
C8B C9B C10B C5B 0.1(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1A H1A O4B 0.82 1.67 2.480(2) 171.3 1_645
N1B H1B3 O3B 0.89 1.82 2.703(2) 174.8 1_655
N1A H1A1 O1A 0.89 2.13 2.940(2) 151.0 2_655
N1A H1A2 O2B 0.89 1.91 2.793(3) 173.9 2_645
N1A H1A3 O4A 0.89 1.88 2.754(2) 166.6 4_565
N1B H1B1 O2A 0.89 2.00 2.863(3) 163.6 3_756
O3A H3A O1B 0.82 1.67 2.474(2) 168.5 .
N1B H1B2 O3A 0.89 2.26 3.001(2) 140.3 .
N1B H1B2 O2B 0.89 2.40 3.084(2) 133.4 .

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.046
####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1485474'
_audit_update_record             
;
2016-06-14 deposited with the CCDC.
2016-07-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H30 N2 O10'
_chemical_formula_weight         482.48

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           ?
_symmetry_space_group_name_H-M   ?

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

_cell_length_a                   14.320(2)
_cell_length_b                   9.6613(13)
_cell_length_c                   17.751(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.215(5)
_cell_angle_gamma                90.00
_cell_volume                     2441.4(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1024
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            35202
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_av_sigmaI/netI    0.0384
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.74
_diffrn_reflns_theta_max         28.70
_reflns_number_total             6191
_reflns_number_gt                3823
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0619P)²+2.5112P] 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       ?
_refine_ls_number_reflns         6191
_refine_ls_number_parameters     427
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0965
_refine_ls_R_factor_gt           0.0462
_refine_ls_wR_factor_ref         0.1548
_refine_ls_wR_factor_gt          0.1069
_refine_ls_goodness_of_fit_ref   0.906
_refine_ls_restrained_S_all      0.906
_refine_ls_shift/su_max          4.515
_refine_ls_shift/su_mean         0.240

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O5 O 0.83811(11) 0.89691(17) 0.82893(10) 0.0411(4) Uani 1 1 d . . .
H5 H 0.882(3) 0.962(4) 0.861(2) 0.097(12) Uiso 1 1 d . . .
O6 O 0.72443(12) 0.96605(19) 0.89590(10) 0.0494(5) Uani 1 1 d . . .
O7 O 0.65812(13) 1.01294(17) 0.70862(10) 0.0476(4) Uani 1 1 d . . .
O8 O 0.70075(13) 0.90706(16) 0.60754(9) 0.0451(4) Uani 1 1 d . . .
C5 C 0.75258(15) 0.8933(2) 0.84700(12) 0.0328(5) Uani 1 1 d . . .
C6 C 0.69103(17) 0.7888(2) 0.80375(13) 0.0362(5) Uani 1 1 d . . .
H6A H 0.7028(17) 0.700(3) 0.8295(15) 0.046(7) Uiso 1 1 d . . .
H6B H 0.6249(19) 0.814(3) 0.8078(15) 0.046(7) Uiso 1 1 d . . .
C7 C 0.70624(18) 0.7782(2) 0.72096(13) 0.0351(5) Uani 1 1 d . . .
H7A H 0.6625(19) 0.709(3) 0.6961(15) 0.050(7) Uiso 1 1 d . . .
H7B H 0.770(2) 0.753(3) 0.7140(16) 0.059(8) Uiso 1 1 d . . .
C8 C 0.68625(14) 0.9102(2) 0.67739(12) 0.0308(4) Uani 1 1 d . . .
O9 O 0.95817(16) 0.7983(2) 0.29920(13) 0.0689(6) Uani 1 1 d . . .
N1 N 0.70835(13) 0.6773(2) 0.51015(11) 0.0344(4) Uani 1 1 d . . .
H1A H 0.736(4) 0.602(6) 0.547(4) 0.11(2) Uiso 1 1 d . . .
H1B H 0.692(4) 0.765(6) 0.539(3) 0.132(19) Uiso 1 1 d . . .
H1C H 0.650(4) 0.628(6) 0.473(3) 0.16(2) Uiso 1 1 d . . .
C9 C 0.77820(14) 0.7109(2) 0.45847(12) 0.0317(5) Uani 1 1 d . . .
C10 C 0.80806(17) 0.8443(3) 0.45232(14) 0.0415(5) Uani 1 1 d . . .
H10 H 0.786(2) 0.916(3) 0.4835(17) 0.064(9) Uiso 1 1 d . . .
C11 C 0.86927(19) 0.8775(3) 0.39946(16) 0.0474(6) Uani 1 1 d . . .
H11 H 0.887(2) 0.970(3) 0.3941(17) 0.063(9) Uiso 1 1 d . . .
C12 C 0.89969(17) 0.7761(3) 0.35370(15) 0.0448(6) Uani 1 1 d . . .
C13 C 0.8698(2) 0.6418(3) 0.36118(18) 0.0568(7) Uani 1 1 d . . .
H13 H 0.891(2) 0.571(4) 0.3287(19) 0.078(10) Uiso 1 1 d . . .
C14 C 0.8092(2) 0.6094(3) 0.41338(17) 0.0492(6) Uani 1 1 d . . .
H14 H 0.787(2) 0.517(3) 0.4182(17) 0.068(9) Uiso 1 1 d . . .
C15 C 0.9916(3) 0.9352(4) 0.2908(3) 0.0822(14) Uani 1 1 d . . .
H15A H 1.029(3) 0.929(4) 0.253(2) 0.091(12) Uiso 1 1 d . . .
H15B H 0.938(3) 0.992(4) 0.273(2) 0.090(12) Uiso 1 1 d . . .
H15C H 1.025(3) 0.968(4) 0.343(2) 0.098(15) Uiso 1 1 d . . .
O10 O 0.66682(14) 0.7399(2) 0.07099(11) 0.0602(5) Uani 1 1 d . . .
N2 N 0.49572(14) 0.8222(2) 0.33492(11) 0.0352(4) Uani 1 1 d . . .
H2C H 0.532(2) 0.899(3) 0.3673(19) 0.087(10) Uiso 1 1 d . . .
H2D H 0.504(3) 0.730(5) 0.365(3) 0.110(14) Uiso 1 1 d . . .
H2E H 0.426(2) 0.854(3) 0.3194(18) 0.084(9) Uiso 1 1 d . . .
C16 C 0.53868(15) 0.8074(2) 0.26435(12) 0.0325(5) Uani 1 1 d . . .
C17 C 0.48535(18) 0.8178(3) 0.19569(14) 0.0434(6) Uani 1 1 d . . .
H17 H 0.424(2) 0.841(3) 0.1949(15) 0.053(8) Uiso 1 1 d . . .
C18 C 0.52596(19) 0.7958(3) 0.12937(15) 0.0480(6) Uani 1 1 d . . .
H18 H 0.486(2) 0.805(3) 0.0816(18) 0.065(9) Uiso 1 1 d . . .
C19 C 0.61985(18) 0.7652(3) 0.13237(13) 0.0418(5) Uani 1 1 d . . .
C20 C 0.67324(19) 0.7586(3) 0.20153(16) 0.0509(6) Uani 1 1 d . . .
H20 H 0.736(2) 0.736(3) 0.2024(18) 0.073(9) Uiso 1 1 d . . .
C21 C 0.63294(18) 0.7793(3) 0.26730(14) 0.0454(6) Uani 1 1 d . . .
H21 H 0.672(2) 0.778(3) 0.3154(18) 0.064(9) Uiso 1 1 d . . .
C22 C 0.6152(3) 0.7363(5) -0.00131(19) 0.0789(11) Uani 1 1 d . . .
H22A H 0.657(3) 0.713(4) -0.037(2) 0.088(11) Uiso 1 1 d . . .
H22B H 0.582(2) 0.823(4) -0.0130(19) 0.072(11) Uiso 1 1 d . . .
H22C H 0.563(3) 0.663(5) -0.001(2) 0.117(14) Uiso 1 1 d . . .
O1 O 0.64415(13) 1.11642(17) 0.53660(9) 0.0448(4) Uani 1 1 d . . .
H1 H 0.670(3) 1.028(4) 0.567(2) 0.100(12) Uiso 1 1 d . . .
O2 O 0.59952(13) 0.96511(16) 0.44708(10) 0.0469(4) Uani 1 1 d . . .
O3 O 0.44051(10) 1.42601(16) 0.39721(10) 0.0405(4) Uani 1 1 d . . .
O4 O 0.55645(11) 1.57850(16) 0.41271(9) 0.0404(4) Uani 1 1 d . . .
C1 C 0.60261(15) 1.0844(2) 0.47107(13) 0.0334(5) Uani 1 1 d . . .
C2 C 0.5544(2) 1.2001(2) 0.42638(17) 0.0458(6) Uani 1 1 d . . .
H2A H 0.489(3) 1.195(4) 0.432(2) 0.094(12) Uiso 1 1 d . . .
H2B H 0.555(2) 1.182(4) 0.371(2) 0.090(11) Uiso 1 1 d . . .
C3 C 0.59031(16) 1.3434(2) 0.44588(16) 0.0386(5) Uani 1 1 d . . .
H3A H 0.651(2) 1.359(3) 0.4258(18) 0.077(10) Uiso 1 1 d . . .
H3B H 0.603(2) 1.355(3) 0.4981(19) 0.067(9) Uiso 1 1 d . . .
C4 C 0.52504(14) 1.4581(2) 0.41597(12) 0.0300(4) 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
O5 C5 1.300(3) . ?
O5 H5 1.02(4) . ?
O6 C5 1.219(3) . ?
O7 C8 1.226(3) . ?
O8 C8 1.279(3) . ?
C5 C6 1.496(3) . ?
C6 C7 1.512(3) . ?
C6 H6A 0.98(3) . ?
C6 H6B 0.99(3) . ?
C7 C8 1.503(3) . ?
C7 H7A 0.99(3) . ?
C7 H7B 0.96(3) . ?
O9 C12 1.363(3) . ?
O9 C15 1.420(4) . ?
N1 C9 1.465(3) . ?
N1 H1A 1.02(6) . ?
N1 H1B 1.03(5) . ?
N1 H1C 1.11(6) . ?
C9 C10 1.366(3) . ?
C9 C14 1.370(3) . ?
C10 C11 1.389(3) . ?
C10 H10 0.96(3) . ?
C11 C12 1.373(4) . ?
C11 H11 0.94(3) . ?
C12 C13 1.377(4) . ?
C13 C14 1.373(4) . ?
C13 H13 0.97(3) . ?
C14 H14 0.95(3) . ?
C15 H15A 0.90(4) . ?
C15 H15B 0.96(4) . ?
C15 H15C 1.05(4) . ?
O10 C19 1.363(3) . ?
O10 C22 1.411(4) . ?
N2 C16 1.461(3) . ?
N2 H2C 1.04(3) . ?
N2 H2D 1.04(5) . ?
N2 H2E 1.05(3) . ?
C16 C17 1.370(3) . ?
C16 C21 1.372(3) . ?
C17 C18 1.385(4) . ?
C17 H17 0.90(3) . ?
C18 C19 1.372(4) . ?
C18 H18 0.97(3) . ?
C19 C20 1.376(4) . ?
C20 C21 1.372(4) . ?
C20 H20 0.92(3) . ?
C21 H21 0.97(3) . ?
C22 H22A 0.94(4) . ?
C22 H22B 0.98(4) . ?
C22 H22C 1.03(5) . ?
O1 C1 1.286(3) . ?
O1 H1 1.05(4) . ?
O2 C1 1.228(3) . ?
O3 C4 1.259(3) . ?
O4 C4 1.251(3) . ?
C1 C2 1.496(3) . ?
C2 C3 1.504(3) . ?
C2 H2A 0.95(4) . ?
C2 H2B 1.00(4) . ?
C3 C4 1.509(3) . ?
C3 H3A 0.99(3) . ?
C3 H3B 0.93(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O5 H5 115(2) . . ?
O6 C5 O5 123.6(2) . . ?
O6 C5 C6 122.2(2) . . ?
O5 C5 C6 114.2(2) . . ?
C5 C6 C7 113.93(19) . . ?
C5 C6 H6A 106.7(15) . . ?
C7 C6 H6A 111.1(15) . . ?
C5 C6 H6B 108.1(15) . . ?
C7 C6 H6B 109.1(15) . . ?
H6A C6 H6B 108(2) . . ?
C8 C7 C6 113.76(19) . . ?
C8 C7 H7A 105.7(16) . . ?
C6 C7 H7A 109.2(16) . . ?
C8 C7 H7B 106.3(18) . . ?
C6 C7 H7B 112.3(18) . . ?
H7A C7 H7B 109(2) . . ?
O7 C8 O8 123.6(2) . . ?
O7 C8 C7 120.5(2) . . ?
O8 C8 C7 115.87(18) . . ?
C12 O9 C15 117.4(2) . . ?
C9 N1 H1A 108(4) . . ?
C9 N1 H1B 110(3) . . ?
H1A N1 H1B 111(4) . . ?
C9 N1 H1C 104(3) . . ?
H1A N1 H1C 107(4) . . ?
H1B N1 H1C 117(4) . . ?
C10 C9 C14 120.3(2) . . ?
C10 C9 N1 120.0(2) . . ?
C14 C9 N1 119.5(2) . . ?
C9 C10 C11 119.8(2) . . ?
C9 C10 H10 120.7(18) . . ?
C11 C10 H10 119.5(18) . . ?
C12 C11 C10 119.9(2) . . ?
C12 C11 H11 120.9(18) . . ?
C10 C11 H11 119.1(18) . . ?
O9 C12 C11 124.5(2) . . ?
O9 C12 C13 116.0(2) . . ?
C11 C12 C13 119.5(2) . . ?
C14 C13 C12 120.4(2) . . ?
C14 C13 H13 120(2) . . ?
C12 C13 H13 119(2) . . ?
C9 C14 C13 120.0(2) . . ?
C9 C14 H14 119.0(19) . . ?
C13 C14 H14 121.0(19) . . ?
O9 C15 H15A 105(2) . . ?
O9 C15 H15B 107(2) . . ?
H15A C15 H15B 108(3) . . ?
O9 C15 H15C 108(2) . . ?
H15A C15 H15C 115(3) . . ?
H15B C15 H15C 113(3) . . ?
C19 O10 C22 118.4(3) . . ?
C16 N2 H2C 108.3(18) . . ?
C16 N2 H2D 109(2) . . ?
H2C N2 H2D 108(3) . . ?
C16 N2 H2E 106.2(17) . . ?
H2C N2 H2E 110(2) . . ?
H2D N2 H2E 116(3) . . ?
C17 C16 C21 120.0(2) . . ?
C17 C16 N2 120.6(2) . . ?
C21 C16 N2 119.4(2) . . ?
C16 C17 C18 120.0(2) . . ?
C16 C17 H17 118.5(18) . . ?
C18 C17 H17 121.4(18) . . ?
C19 C18 C17 120.0(2) . . ?
C19 C18 H18 122.4(18) . . ?
C17 C18 H18 117.6(18) . . ?
O10 C19 C18 125.0(2) . . ?
O10 C19 C20 115.5(2) . . ?
C18 C19 C20 119.5(2) . . ?
C21 C20 C19 120.6(2) . . ?
C21 C20 H20 121(2) . . ?
C19 C20 H20 118(2) . . ?
C16 C21 C20 119.9(2) . . ?
C16 C21 H21 120.2(18) . . ?
C20 C21 H21 119.8(18) . . ?
O10 C22 H22A 108(2) . . ?
O10 C22 H22B 112(2) . . ?
H22A C22 H22B 113(3) . . ?
O10 C22 H22C 109(2) . . ?
H22A C22 H22C 111(3) . . ?
H22B C22 H22C 105(3) . . ?
C1 O1 H1 112(2) . . ?
O2 C1 O1 122.4(2) . . ?
O2 C1 C2 121.4(2) . . ?
O1 C1 C2 116.2(2) . . ?
C1 C2 C3 116.0(2) . . ?
C1 C2 H2A 108(2) . . ?
C3 C2 H2A 110(2) . . ?
C1 C2 H2B 110(2) . . ?
C3 C2 H2B 111(2) . . ?
H2A C2 H2B 102(3) . . ?
C2 C3 C4 114.31(19) . . ?
C2 C3 H3A 110.3(19) . . ?
C4 C3 H3A 107.5(19) . . ?
C2 C3 H3B 111(2) . . ?
C4 C3 H3B 107.9(19) . . ?
H3A C3 H3B 105(3) . . ?
O4 C4 O3 123.86(19) . . ?
O4 C4 C3 119.16(19) . . ?
O3 C4 C3 116.96(19) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O6 C5 C6 C7 141.9(2) . . . . ?
O5 C5 C6 C7 -39.5(3) . . . . ?
C5 C6 C7 C8 -61.2(3) . . . . ?
C6 C7 C8 O7 -1.7(3) . . . . ?
C6 C7 C8 O8 178.1(2) . . . . ?
C14 C9 C10 C11 0.8(4) . . . . ?
N1 C9 C10 C11 -175.5(2) . . . . ?
C9 C10 C11 C12 -0.1(4) . . . . ?
C15 O9 C12 C11 1.7(5) . . . . ?
C15 O9 C12 C13 -179.0(3) . . . . ?
C10 C11 C12 O9 178.7(3) . . . . ?
C10 C11 C12 C13 -0.6(4) . . . . ?
O9 C12 C13 C14 -178.6(3) . . . . ?
C11 C12 C13 C14 0.7(5) . . . . ?
C10 C9 C14 C13 -0.7(4) . . . . ?
N1 C9 C14 C13 175.6(3) . . . . ?
C12 C13 C14 C9 -0.1(5) . . . . ?
C21 C16 C17 C18 2.0(4) . . . . ?
N2 C16 C17 C18 -176.4(2) . . . . ?
C16 C17 C18 C19 -0.7(4) . . . . ?
C22 O10 C19 C18 -4.1(4) . . . . ?
C22 O10 C19 C20 176.0(3) . . . . ?
C17 C18 C19 O10 179.1(2) . . . . ?
C17 C18 C19 C20 -1.0(4) . . . . ?
O10 C19 C20 C21 -178.6(2) . . . . ?
C18 C19 C20 C21 1.5(4) . . . . ?
C17 C16 C21 C20 -1.5(4) . . . . ?
N2 C16 C21 C20 176.9(2) . . . . ?
C19 C20 C21 C16 -0.2(4) . . . . ?
O2 C1 C2 C3 -158.5(2) . . . . ?
O1 C1 C2 C3 23.9(4) . . . . ?
C1 C2 C3 C4 -164.2(2) . . . . ?
C2 C3 C4 O4 -162.9(2) . . . . ?
C2 C3 C4 O3 18.7(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2C O2 1.04(3) 1.75(3) 2.727(2) 155(3) .
N2 H2D O4 1.04(5) 1.81(5) 2.819(2) 162(4) 1_545

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        28.70
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.076
####################################################################### 
# 
# 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 1485475'
_audit_update_record             
;
2016-06-14 deposited with the CCDC.
2016-07-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H14 N2 O5'
_chemical_formula_weight         242.23

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'

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

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

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

_cell_length_a                   10.5893(8)
_cell_length_b                   14.2294(11)
_cell_length_c                   7.4272(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.524(3)
_cell_angle_gamma                90
_cell_volume                     1115.64(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_F_000             512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    0.117
_shelx_estimated_absorpt_T_min   0.960
_shelx_estimated_absorpt_T_max   0.971
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10306
_diffrn_reflns_av_unetI/netI     0.0249
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.402
_diffrn_reflns_theta_max         24.495
_diffrn_reflns_theta_full        24.495
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1862
_reflns_number_gt                1530
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0655P)²+0.9883P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1862
_refine_ls_number_parameters     169
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0516
_refine_ls_wR_factor_ref         0.1488
_refine_ls_wR_factor_gt          0.1402
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.074
_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
N1 N 0.7686(2) 0.34495(17) 0.8279(3) 0.0382(5) Uani 1 1 d D . . . .
H1A H 0.819(3) 0.342(2) 0.733(3) 0.057 Uiso 1 1 d D U . . .
H1B H 0.779(3) 0.4035(15) 0.874(4) 0.057 Uiso 1 1 d D U . . .
H1C H 0.796(3) 0.3039(19) 0.916(3) 0.057 Uiso 1 1 d D U . . .
N2 N 0.6787(3) 0.16695(19) 0.7220(4) 0.0604(7) Uani 1 1 d D . . . .
H2C H 0.738(3) 0.165(3) 0.819(4) 0.073 Uiso 1 1 d D U . . .
H2D H 0.633(3) 0.1131(18) 0.715(5) 0.073 Uiso 1 1 d D U . . .
C5 C 0.6356(2) 0.32977(19) 0.7667(3) 0.0387(6) Uani 1 1 d . . . . .
C6 C 0.5946(2) 0.24104(19) 0.7197(3) 0.0408(6) Uani 1 1 d . . . . .
C7 C 0.4674(3) 0.2307(2) 0.6555(4) 0.0526(8) Uani 1 1 d . . . . .
H7 H 0.4364 0.1714 0.6231 0.063 Uiso 1 1 calc R U . . .
C8 C 0.3887(3) 0.3063(3) 0.6399(5) 0.0630(9) Uani 1 1 d . . . . .
H8 H 0.3050 0.2982 0.5944 0.076 Uiso 1 1 calc R U . . .
C9 C 0.4306(3) 0.3935(3) 0.6899(6) 0.0807(12) Uani 1 1 d . . . . .
H9 H 0.3751 0.4443 0.6825 0.097 Uiso 1 1 calc R U . . .
C10 C 0.5552(3) 0.4062(2) 0.7516(5) 0.0644(9) Uani 1 1 d . . . . .
H10 H 0.5851 0.4659 0.7829 0.077 Uiso 1 1 calc R U . . .
O1 O 0.92010(17) 0.61809(14) 0.4074(2) 0.0438(5) Uani 1 1 d . . . . .
O2 O 1.11032(16) 0.67888(13) 0.4788(2) 0.0402(5) Uani 1 1 d . . . . .
O3 O 0.8122(2) 0.51817(14) 1.0227(2) 0.0500(5) Uani 1 1 d . . . . .
O4 O 0.9190(2) 0.65041(16) 1.0726(2) 0.0605(7) Uani 1 1 d . . . . .
H4 H 0.9160 0.6349 1.1785 0.091 Uiso 1 1 calc R U . . .
O5 O 0.8046(2) 0.53353(16) 0.6734(3) 0.0616(6) Uani 1 1 d . . . . .
H5 H 0.8200 0.5362 0.5670 0.092 Uiso 1 1 calc R U . . .
C1 C 1.0084(2) 0.64337(17) 0.5192(3) 0.0328(6) Uani 1 1 d . . . . .
C2 C 0.9949(3) 0.6268(2) 0.7175(3) 0.0446(7) Uani 1 1 d . . . . .
H2A H 1.0464 0.5729 0.7554 0.054 Uiso 1 1 calc R U . . .
H2B H 1.0292 0.6808 0.7841 0.054 Uiso 1 1 calc R U . . .
C3 C 0.8645(3) 0.6102(2) 0.7696(3) 0.0458(7) Uani 1 1 d . . . . .
H3 H 0.8141 0.6671 0.7441 0.055 Uiso 1 1 calc R U . . .
C4 C 0.8628(2) 0.58683(19) 0.9682(3) 0.0387(6) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C5 1.462(3) . ?
N1 H1A 0.922(18) . ?
N1 H1B 0.904(18) . ?
N1 H1C 0.906(18) . ?
N2 C6 1.379(4) . ?
N2 H2C 0.916(19) . ?
N2 H2D 0.905(18) . ?
C5 C6 1.371(4) . ?
C5 C10 1.380(4) . ?
C6 C7 1.401(4) . ?
C7 C8 1.360(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.359(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.374(5) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
O1 C1 1.253(3) . ?
O2 C1 1.249(3) . ?
O3 C4 1.200(3) . ?
O4 C4 1.304(3) . ?
O4 H4 0.8200 . ?
O5 C3 1.425(3) . ?
O5 H5 0.8200 . ?
C1 C2 1.509(3) . ?
C2 C3 1.482(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.513(4) . ?
C3 H3 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 N1 H1A 111(2) . . ?
C5 N1 H1B 110(2) . . ?
H1A N1 H1B 106(3) . . ?
C5 N1 H1C 112(2) . . ?
H1A N1 H1C 111(3) . . ?
H1B N1 H1C 107(3) . . ?
C6 N2 H2C 116(2) . . ?
C6 N2 H2D 108(2) . . ?
H2C N2 H2D 110(3) . . ?
C6 C5 C10 121.6(3) . . ?
C6 C5 N1 119.5(2) . . ?
C10 C5 N1 118.8(3) . . ?
C5 C6 N2 120.7(2) . . ?
C5 C6 C7 117.4(3) . . ?
N2 C6 C7 121.8(3) . . ?
C8 C7 C6 120.8(3) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C9 C8 C7 120.9(3) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C8 C9 C10 119.7(3) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C9 C10 C5 119.6(3) . . ?
C9 C10 H10 120.2 . . ?
C5 C10 H10 120.2 . . ?
C4 O4 H4 109.5 . . ?
C3 O5 H5 109.5 . . ?
O2 C1 O1 124.8(2) . . ?
O2 C1 C2 116.6(2) . . ?
O1 C1 C2 118.6(2) . . ?
C3 C2 C1 116.2(2) . . ?
C3 C2 H2A 108.2 . . ?
C1 C2 H2A 108.2 . . ?
C3 C2 H2B 108.2 . . ?
C1 C2 H2B 108.2 . . ?
H2A C2 H2B 107.4 . . ?
O5 C3 C2 112.2(2) . . ?
O5 C3 C4 106.4(2) . . ?
C2 C3 C4 111.9(2) . . ?
O5 C3 H3 108.8 . . ?
C2 C3 H3 108.8 . . ?
C4 C3 H3 108.8 . . ?
O3 C4 O4 124.0(2) . . ?
O3 C4 C3 123.2(2) . . ?
O4 C4 C3 112.8(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 C5 C6 N2 174.7(3) . . . . ?
N1 C5 C6 N2 -2.9(4) . . . . ?
C10 C5 C6 C7 0.0(4) . . . . ?
N1 C5 C6 C7 -177.7(2) . . . . ?
C5 C6 C7 C8 0.4(4) . . . . ?
N2 C6 C7 C8 -174.3(3) . . . . ?
C6 C7 C8 C9 -1.5(5) . . . . ?
C7 C8 C9 C10 2.2(6) . . . . ?
C8 C9 C10 C5 -1.8(6) . . . . ?
C6 C5 C10 C9 0.7(5) . . . . ?
N1 C5 C10 C9 178.4(3) . . . . ?
O2 C1 C2 C3 163.6(2) . . . . ?
O1 C1 C2 C3 -18.8(4) . . . . ?
C1 C2 C3 O5 56.0(3) . . . . ?
C1 C2 C3 C4 175.5(2) . . . . ?
O5 C3 C4 O3 -3.9(4) . . . . ?
C2 C3 C4 O3 -126.7(3) . . . . ?
O5 C3 C4 O4 177.9(2) . . . . ?
C2 C3 C4 O4 55.1(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O2 0.922(18) 1.815(19) 2.722(3) 168(3) 3_766
N1 H1B O3 0.904(18) 1.986(19) 2.877(3) 168(3) .
N1 H1B O5 0.904(18) 2.41(3) 2.955(3) 119(2) .
N1 H1C O2 0.906(18) 2.16(2) 2.999(3) 155(3) 2_746
N2 H2C O2 0.916(19) 2.12(2) 3.029(3) 170(3) 2_746
O4 H4 O1 0.82 1.71 2.528(2) 171.6 1_556
O5 H5 O1 0.82 2.02 2.688(3) 138.2 .

_refine_diff_density_max         0.490
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.049

####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1485476'
_audit_update_record             
;
2016-06-14 deposited with the CCDC.
2016-07-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H17 N O6'
_chemical_formula_weight         271.27

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

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

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

_cell_length_a                   5.9736(3)
_cell_length_b                   7.5564(4)
_cell_length_c                   16.1174(7)
_cell_angle_alpha                81.600(2)
_cell_angle_beta                 81.012(2)
_cell_angle_gamma                70.7390(10)
_cell_volume                     674.87(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             288
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14420
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_av_sigmaI/netI    0.0177
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.57
_diffrn_reflns_theta_max         27.50
_reflns_number_total             3087
_reflns_number_gt                2540
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0410P)²+0.1126P] 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       ?
_refine_ls_number_reflns         3087
_refine_ls_number_parameters     340
_refine_ls_number_restraints     265
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0351
_refine_ls_wR_factor_ref         0.0964
_refine_ls_wR_factor_gt          0.0911
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.001

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 -0.0212(13) 0.4563(12) 0.8745(6) 0.0493(17) Uani 0.70 1 d PDU A 1
O2 O 0.3361(7) 0.3249(8) 0.9108(4) 0.0545(13) Uani 0.70 1 d PDU A 1
O3 O 0.2630(10) 1.0080(7) 0.9645(3) 0.0469(8) Uani 0.70 1 d PDU A 1
H3A H 0.2883 1.1088 0.9494 0.070 Uiso 0.70 1 calc PRD A 1
O4 O 0.4904(11) 0.9272(10) 0.8454(4) 0.0580(11) Uani 0.70 1 d PDU A 1
O5 O 0.0176(13) 0.8004(8) 0.8468(6) 0.0519(14) Uani 0.70 1 d PDU A 1
H5A H -0.0881 0.7579 0.8410 0.078 Uiso 0.70 1 calc PRD A 1
C1 C 0.1728(11) 0.4660(8) 0.8847(4) 0.0343(12) Uani 0.70 1 d PDU A 1
C2 C 0.2237(3) 0.6526(2) 0.86291(13) 0.0309(3) Uani 0.70 1 d PDU A 1
H2A H 0.3376 0.6432 0.8117 0.037 Uiso 0.70 1 calc PR A 1
C3 C 0.3322(4) 0.6996(2) 0.93220(13) 0.0350(4) Uani 0.70 1 d PDU A 1
H3F H 0.4824 0.6024 0.9412 0.042 Uiso 0.70 1 calc PR A 1
H3E H 0.2257 0.7032 0.9844 0.042 Uiso 0.70 1 calc PR A 1
C4 C 0.3745(8) 0.8890(6) 0.9086(2) 0.0298(8) Uani 0.70 1 d PDU A 1
O1' O -0.038(3) 0.471(3) 0.8837(13) 0.0350(18) Uani 0.30 1 d PDU B 2
O2' O 0.341(2) 0.3298(17) 0.9226(10) 0.051(2) Uani 0.30 1 d PDU B 2
O3' O 0.282(2) 0.9825(17) 0.9400(7) 0.056(2) Uani 0.30 1 d PDU B 2
H3B H 0.2880 1.0904 0.9298 0.084 Uiso 0.30 1 calc PRD B 2
O4' O 0.535(2) 0.935(2) 0.8260(9) 0.054(2) Uani 0.30 1 d PDU B 2
O5' O -0.008(3) 0.7947(15) 0.8584(13) 0.051(3) Uani 0.30 1 d PDU B 2
H5B H -0.1240 0.7577 0.8615 0.076 Uiso 0.30 1 calc PRD B 2
C1' C 0.159(2) 0.4620(16) 0.9031(10) 0.027(2) Uani 0.30 1 d PDU B 2
C2' C 0.1627(7) 0.6664(5) 0.9093(3) 0.0363(8) Uani 0.30 1 d PDU B 2
H2B H 0.1096 0.6942 0.9680 0.044 Uiso 0.30 1 calc PR B 2
C3' C 0.4042(8) 0.6843(6) 0.8875(4) 0.0467(11) Uani 0.30 1 d PDU B 2
H3C H 0.4733 0.6315 0.8345 0.056 Uiso 0.30 1 calc PR B 2
H3D H 0.5030 0.6101 0.9306 0.056 Uiso 0.30 1 calc PR B 2
C4' C 0.411(2) 0.8811(16) 0.8796(7) 0.043(3) Uani 0.30 1 d PDU B 2
N1 N 0.80978(18) 0.19063(13) 0.83631(6) 0.0365(2) Uani 1 1 d D . .
H1A H 0.649(2) 0.228(2) 0.8579(9) 0.055 Uiso 1 1 d D . .
H1B H 0.886(2) 0.2654(19) 0.8567(9) 0.055 Uiso 1 1 d D . .
H1C H 0.874(2) 0.0687(18) 0.8542(9) 0.055 Uiso 1 1 d D . .
C5 C 0.8370(2) 0.21722(15) 0.74418(8) 0.0389(3) Uani 1 1 d D . .
O6 O 0.9201(17) 0.2883(15) 0.4840(6) 0.088(2) Uani 0.70 1 d PDU C 1
C6 C 1.0697(9) 0.1578(9) 0.7038(3) 0.0418(9) Uani 0.70 1 d PDU C 1
H6A H 1.2007 0.1085 0.7342 0.050 Uiso 0.70 1 calc PR C 1
C7 C 1.0965(19) 0.1757(15) 0.6157(5) 0.0563(15) Uani 0.70 1 d PDU C 1
H7A H 1.2479 0.1271 0.5871 0.068 Uiso 0.70 1 calc PR C 1
C8 C 0.9114(17) 0.261(2) 0.5702(6) 0.0614(19) Uani 0.70 1 d PDU C 1
C9 C 0.6871(14) 0.3181(16) 0.6140(7) 0.067(2) Uani 0.70 1 d PDU C 1
H9A H 0.5567 0.3754 0.5838 0.081 Uiso 0.70 1 calc PR C 1
C10 C 0.6483(14) 0.2937(12) 0.7010(6) 0.0580(19) Uani 0.70 1 d PDU C 1
H10A H 0.4942 0.3298 0.7290 0.070 Uiso 0.70 1 calc PR C 1
C11 C 1.1488(17) 0.2277(13) 0.4373(4) 0.086(2) Uani 0.70 1 d PDU C 1
H11A H 1.2239 0.0935 0.4505 0.103 Uiso 0.70 1 calc PR C 1
H11B H 1.2508 0.2942 0.4504 0.103 Uiso 0.70 1 calc PR C 1
C12 C 1.108(2) 0.2720(11) 0.3453(4) 0.107(3) Uani 0.70 1 d PDU C 1
H12A H 1.0072 0.2047 0.3334 0.161 Uiso 0.70 1 calc PR C 1
H12B H 1.2580 0.2345 0.3106 0.161 Uiso 0.70 1 calc PR C 1
H12C H 1.0317 0.4049 0.3335 0.161 Uiso 0.70 1 calc PR C 1
O6' O 0.872(4) 0.319(3) 0.4847(12) 0.066(2) Uani 0.30 1 d PDU C 2
C6' C 1.038(3) 0.171(3) 0.6939(11) 0.068(4) Uani 0.30 1 d PDU C 2
H6B H 1.1729 0.1012 0.7202 0.082 Uiso 0.30 1 calc PR C 2
C7' C 1.078(4) 0.211(3) 0.6077(13) 0.056(4) Uani 0.30 1 d PDU C 2
H7B H 1.2283 0.1946 0.5777 0.068 Uiso 0.30 1 calc PR C 2
C8' C 0.865(3) 0.279(4) 0.5710(12) 0.047(3) Uani 0.30 1 d PDU C 2
C9' C 0.637(3) 0.336(3) 0.6139(11) 0.042(2) Uani 0.30 1 d PDU C 2
H9B H 0.5016 0.3890 0.5863 0.051 Uiso 0.30 1 calc PR C 2
C10' C 0.627(3) 0.307(2) 0.7023(10) 0.039(3) Uani 0.30 1 d PDU C 2
H10B H 0.4799 0.3464 0.7347 0.047 Uiso 0.30 1 calc PR C 2
C11' C 1.085(4) 0.249(3) 0.4320(12) 0.077(4) Uani 0.30 1 d PDU C 2
H11C H 1.1491 0.1134 0.4445 0.092 Uiso 0.30 1 calc PR C 2
H11D H 1.2018 0.3050 0.4416 0.092 Uiso 0.30 1 calc PR C 2
C12' C 1.033(6) 0.297(3) 0.3393(13) 0.134(8) Uani 0.30 1 d PDU C 2
H12D H 0.8867 0.2746 0.3339 0.201 Uiso 0.30 1 calc PR C 2
H12E H 1.1614 0.2196 0.3041 0.201 Uiso 0.30 1 calc PR C 2
H12F H 1.0170 0.4274 0.3223 0.201 Uiso 0.30 1 calc PR C 2


_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 1.223(6) . ?
O2 C1 1.256(6) . ?
O3 C4 1.310(4) . ?
O3 H3A 0.8200 . ?
O4 C4 1.195(4) . ?
O5 C2 1.392(5) . ?
O5 H5A 0.8200 . ?
C1 C2 1.519(6) . ?
C2 C3 1.512(2) . ?
C2 H2A 0.9800 . ?
C3 C4 1.519(4) . ?
C3 H3F 0.9700 . ?
C3 H3E 0.9700 . ?
O1' C1' 1.239(12) . ?
O2' C1' 1.257(12) . ?
O3' C4' 1.314(9) . ?
O3' H3B 0.8200 . ?
O4' C4' 1.166(12) . ?
O5' C2' 1.425(10) . ?
O5' H5B 0.8200 . ?
C1' C2' 1.571(11) . ?
C2' C3' 1.476(6) . ?
C2' H2B 0.9800 . ?
C3' C4' 1.488(11) . ?
C3' H3C 0.9700 . ?
C3' H3D 0.9700 . ?
N1 C5 1.4597(16) . ?
N1 H1A 0.932(13) . ?
N1 H1B 0.950(12) . ?
N1 H1C 0.896(13) . ?
C5 C6' 1.314(14) . ?
C5 C10 1.337(6) . ?
C5 C6 1.396(5) . ?
C5 C10' 1.433(9) . ?
O6 C8 1.371(8) . ?
O6 C11 1.417(8) . ?
C6 C7 1.397(8) . ?
C6 H6A 0.9300 . ?
C7 C8 1.348(8) . ?
C7 H7A 0.9300 . ?
C8 C9 1.375(8) . ?
C9 C10 1.381(8) . ?
C9 H9A 0.9300 . ?
C10 H10A 0.9300 . ?
C11 C12 1.513(7) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
O6' C8' 1.376(17) . ?
O6' C11' 1.404(17) . ?
C6' C7' 1.379(17) . ?
C6' H6B 0.9300 . ?
C7' C8' 1.393(16) . ?
C7' H7B 0.9300 . ?
C8' C9' 1.387(16) . ?
C9' C10' 1.404(14) . ?
C9' H9B 0.9300 . ?
C10' H10B 0.9300 . ?
C11' C12' 1.540(16) . ?
C11' H11C 0.9700 . ?
C11' H11D 0.9700 . ?
C12' H12D 0.9600 . ?
C12' H12E 0.9600 . ?
C12' H12F 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 O2 122.2(7) . . ?
O1 C1 C2 119.6(5) . . ?
O2 C1 C2 118.2(5) . . ?
O5 C2 C3 108.5(3) . . ?
O5 C2 C1 111.5(4) . . ?
C3 C2 C1 112.3(3) . . ?
O5 C2 H2A 108.1 . . ?
C3 C2 H2A 108.1 . . ?
C1 C2 H2A 108.1 . . ?
C2 C3 C4 110.5(2) . . ?
C2 C3 H3F 109.6 . . ?
C4 C3 H3F 109.6 . . ?
C2 C3 H3E 109.6 . . ?
C4 C3 H3E 109.6 . . ?
H3F C3 H3E 108.1 . . ?
O4 C4 O3 123.8(5) . . ?
O4 C4 C3 124.0(5) . . ?
O3 C4 C3 112.2(4) . . ?
C4' O3' H3B 109.5 . . ?
C2' O5' H5B 109.5 . . ?
O1' C1' O2' 134.7(14) . . ?
O1' C1' C2' 109.2(12) . . ?
O2' C1' C2' 116.0(11) . . ?
O5' C2' C3' 113.3(10) . . ?
O5' C2' C1' 107.9(8) . . ?
C3' C2' C1' 112.6(6) . . ?
O5' C2' H2B 107.6 . . ?
C3' C2' H2B 107.6 . . ?
C1' C2' H2B 107.6 . . ?
C2' C3' C4' 114.4(6) . . ?
C2' C3' H3C 108.7 . . ?
C4' C3' H3C 108.7 . . ?
C2' C3' H3D 108.7 . . ?
C4' C3' H3D 108.7 . . ?
H3C C3' H3D 107.6 . . ?
O4' C4' O3' 123.3(13) . . ?
O4' C4' C3' 121.4(13) . . ?
O3' C4' C3' 115.2(9) . . ?
C5 N1 H1A 110.9(9) . . ?
C5 N1 H1B 109.0(8) . . ?
H1A N1 H1B 108.4(12) . . ?
C5 N1 H1C 110.1(9) . . ?
H1A N1 H1C 108.1(13) . . ?
H1B N1 H1C 110.4(13) . . ?
C6' C5 C10 111.9(9) . . ?
C6' C5 C6 10.1(10) . . ?
C10 C5 C6 122.0(5) . . ?
C6' C5 C10' 115.1(11) . . ?
C10 C5 C10' 3.7(12) . . ?
C6 C5 C10' 125.1(9) . . ?
C6' C5 N1 126.5(8) . . ?
C10 C5 N1 121.5(5) . . ?
C6 C5 N1 116.5(3) . . ?
C10' C5 N1 118.4(8) . . ?
C8 O6 C11 116.8(8) . . ?
C5 C6 C7 116.8(6) . . ?
C5 C6 H6A 121.6 . . ?
C7 C6 H6A 121.6 . . ?
C8 C7 C6 122.6(8) . . ?
C8 C7 H7A 118.7 . . ?
C6 C7 H7A 118.7 . . ?
C7 C8 O6 126.9(8) . . ?
C7 C8 C9 117.4(9) . . ?
O6 C8 C9 115.6(9) . . ?
C8 C9 C10 122.5(8) . . ?
C8 C9 H9A 118.8 . . ?
C10 C9 H9A 118.8 . . ?
C5 C10 C9 118.5(8) . . ?
C5 C10 H10A 120.7 . . ?
C9 C10 H10A 120.7 . . ?
O6 C11 C12 106.0(8) . . ?
O6 C11 H11A 110.5 . . ?
C12 C11 H11A 110.5 . . ?
O6 C11 H11B 110.5 . . ?
C12 C11 H11B 110.5 . . ?
H11A C11 H11B 108.7 . . ?
C8' O6' C11' 120.4(17) . . ?
C5 C6' C7' 129.1(16) . . ?
C5 C6' H6B 115.5 . . ?
C7' C6' H6B 115.5 . . ?
C6' C7' C8' 111.8(19) . . ?
C6' C7' H7B 124.1 . . ?
C8' C7' H7B 124.1 . . ?
O6' C8' C9' 113.8(16) . . ?
O6' C8' C7' 119.8(18) . . ?
C9' C8' C7' 125.8(18) . . ?
C8' C9' C10' 115.0(17) . . ?
C8' C9' H9B 122.5 . . ?
C10' C9' H9B 122.5 . . ?
C9' C10' C5 122.0(16) . . ?
C9' C10' H10B 119.0 . . ?
C5 C10' H10B 119.0 . . ?
O6' C11' C12' 108.9(18) . . ?
O6' C11' H11C 109.9 . . ?
C12' C11' H11C 109.9 . . ?
O6' C11' H11D 109.9 . . ?
C12' C11' H11D 109.9 . . ?
H11C C11' H11D 108.3 . . ?
C11' C12' H12D 109.5 . . ?
C11' C12' H12E 109.5 . . ?
H12D C12' H12E 109.5 . . ?
C11' C12' H12F 109.5 . . ?
H12D C12' H12F 109.5 . . ?
H12E C12' H12F 109.5 . . ?

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
O1 C1 C2 O5 10.5(9) . . . . ?
O2 C1 C2 O5 -171.3(6) . . . . ?
O1 C1 C2 C3 132.5(6) . . . . ?
O2 C1 C2 C3 -49.3(7) . . . . ?
O5 C2 C3 C4 -54.9(5) . . . . ?
C1 C2 C3 C4 -178.7(3) . . . . ?
C2 C3 C4 O4 -55.9(7) . . . . ?
C2 C3 C4 O3 122.1(4) . . . . ?
O1' C1' C2' O5' -24.0(17) . . . . ?
O2' C1' C2' O5' 159.7(15) . . . . ?
O1' C1' C2' C3' -149.8(12) . . . . ?
O2' C1' C2' C3' 33.9(14) . . . . ?
O5' C2' C3' C4' 48.2(10) . . . . ?
C1' C2' C3' C4' 171.1(8) . . . . ?
C2' C3' C4' O4' -139.1(15) . . . . ?
C2' C3' C4' O3' 45.3(13) . . . . ?
C6' C5 C6 C7 -1(6) . . . . ?
C10 C5 C6 C7 -2.2(9) . . . . ?
C10' C5 C6 C7 -4.6(12) . . . . ?
N1 C5 C6 C7 177.5(6) . . . . ?
C5 C6 C7 C8 5.7(14) . . . . ?
C6 C7 C8 O6 178.8(13) . . . . ?
C6 C7 C8 C9 -5.1(19) . . . . ?
C11 O6 C8 C7 -3(2) . . . . ?
C11 O6 C8 C9 -179.0(12) . . . . ?
C7 C8 C9 C10 1(2) . . . . ?
O6 C8 C9 C10 177.6(12) . . . . ?
C6' C5 C10 C9 -1.8(14) . . . . ?
C6 C5 C10 C9 -1.5(11) . . . . ?
C10' C5 C10 C9 146(18) . . . . ?
N1 C5 C10 C9 178.8(7) . . . . ?
C8 C9 C10 C5 2.3(17) . . . . ?
C8 O6 C11 C12 179.5(11) . . . . ?
C10 C5 C6' C7' 9(3) . . . . ?
C6 C5 C6' C7' -170(8) . . . . ?
C10' C5 C6' C7' 6(3) . . . . ?
N1 C5 C6' C7' -172.0(18) . . . . ?
C5 C6' C7' C8' -13(4) . . . . ?
C11' O6' C8' C9' -172(2) . . . . ?
C11' O6' C8' C7' 16(4) . . . . ?
C6' C7' C8' O6' -177(3) . . . . ?
C6' C7' C8' C9' 12(4) . . . . ?
O6' C8' C9' C10' -176(2) . . . . ?
C7' C8' C9' C10' -5(4) . . . . ?
C8' C9' C10' C5 -3(3) . . . . ?
C6' C5 C10' C9' 2(2) . . . . ?
C10 C5 C10' C9' -30(16) . . . . ?
C6 C5 C10' C9' 3(2) . . . . ?
N1 C5 C10' C9' -179.3(15) . . . . ?
C8' O6' C11' C12' 174(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3A O2 0.82 1.76 2.577(8) 176.2 1_565
O5 H5A O1 0.82 2.18 2.654(10) 116.9 .
O5 H5A O4 0.82 2.41 2.977(9) 126.7 1_455
N1 H1A O2 0.932(13) 1.881(14) 2.807(4) 171.9(13) .
N1 H1B O1 0.950(12) 1.781(15) 2.706(8) 163.5(13) 1_655
N1 H1C O5 0.896(13) 1.936(14) 2.787(5) 157.8(13) 1_645

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.027
