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

####################################################################### 
# 
# 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_ups482kt_0m
_database_code_depnum_ccdc_archive 'CCDC 1030331'
_audit_update_record             
;
2014-10-21 deposited with the CCDC.
2014-12-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H5 O6, C5 H9 N2'
_chemical_formula_sum            'C14 H14 N2 O6'
_chemical_formula_weight         306.27

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   3.8298(4)
_cell_length_b                   13.6659(13)
_cell_length_c                   26.168(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.048(5)
_cell_angle_gamma                90.00
_cell_volume                     1369.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    112
_cell_measurement_theta_min      2.77
_cell_measurement_theta_max      30.86

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             640.0
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.973
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'

_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  'CCD area detector'
_diffrn_measurement_method       'phi omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22270
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_av_sigmaI/netI    0.0275
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         2.77
_diffrn_reflns_theta_max         26.75
_reflns_number_total             2901
_reflns_number_gt                2191
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker Kappa Apex'
_computing_cell_refinement       'Bruker Kappa Apex'
_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)+(0.0620P)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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2901
_refine_ls_number_parameters     203
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0629
_refine_ls_R_factor_gt           0.0446
_refine_ls_wR_factor_ref         0.1351
_refine_ls_wR_factor_gt          0.1262
_refine_ls_goodness_of_fit_ref   1.392
_refine_ls_restrained_S_all      1.392
_refine_ls_shift/su_max          0.002
_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 0.8398(4) 0.96581(9) 0.32447(5) 0.0473(4) Uani 1 1 d . . .
O2 O 1.0531(4) 0.93732(9) 0.40201(5) 0.0457(4) Uani 1 1 d . . .
O3 O 1.0624(4) 0.62029(10) 0.47917(5) 0.0468(4) Uani 1 1 d . . .
H3 H 1.0992 0.5794 0.5016 0.070 Uiso 1 1 calc R . .
O4 O 0.8070(4) 0.49266(9) 0.44127(5) 0.0480(4) Uani 1 1 d . . .
O5 O 0.4451(4) 0.52546(9) 0.26158(5) 0.0514(4) Uani 1 1 d . . .
H5 H 0.3623 0.5068 0.2341 0.077 Uiso 1 1 calc R . .
O6 O 0.3243(4) 0.67220(10) 0.22946(5) 0.0452(4) Uani 1 1 d . . .
N1 N 0.9105(4) 0.67329(10) 0.13837(6) 0.0322(4) Uani 1 1 d . . .
H1 H 1.0182 0.6512 0.1651 0.039 Uiso 1 1 calc R . .
N2 N 0.8019(4) 0.61823(11) 0.09900(5) 0.0338(4) Uani 1 1 d . . .
H2 H 0.8280 0.5560 0.0961 0.041 Uiso 1 1 calc R . .
C1 C 0.8182(4) 0.80318(12) 0.35739(6) 0.0255(4) Uani 1 1 d . . .
C2 C 0.8964(4) 0.74294(12) 0.39873(6) 0.0264(4) Uani 1 1 d . . .
H2A H 1.0008 0.7693 0.4280 0.032 Uiso 1 1 calc R . .
C3 C 0.8203(4) 0.64364(12) 0.39683(6) 0.0255(4) Uani 1 1 d . . .
C4 C 0.6727(4) 0.60326(12) 0.35276(6) 0.0262(4) Uani 1 1 d . . .
H4 H 0.6254 0.5366 0.3512 0.031 Uiso 1 1 calc R . .
C5 C 0.5965(4) 0.66262(12) 0.31121(6) 0.0258(4) Uani 1 1 d . . .
C6 C 0.6656(4) 0.76286(12) 0.31403(6) 0.0278(4) Uani 1 1 d . . .
H6 H 0.6082 0.8029 0.2864 0.033 Uiso 1 1 calc R . .
C7 C 0.9059(5) 0.91043(13) 0.36053(6) 0.0313(4) Uani 1 1 d . . .
C8 C 0.9006(5) 0.58023(12) 0.44156(6) 0.0295(4) Uani 1 1 d . . .
C9 C 0.4407(4) 0.62154(12) 0.26320(6) 0.0288(4) Uani 1 1 d . . .
C10 C 0.9191(6) 0.84443(15) 0.16846(8) 0.0490(5) Uani 1 1 d . . .
H10A H 0.7590 0.8416 0.1962 0.074 Uiso 1 1 calc R . .
H10B H 0.9037 0.9074 0.1523 0.074 Uiso 1 1 calc R . .
H10C H 1.1527 0.8343 0.1813 0.074 Uiso 1 1 calc R . .
C11 C 0.8295(5) 0.76711(12) 0.13063(7) 0.0322(4) Uani 1 1 d . . .
C12 C 0.6592(5) 0.77120(14) 0.08418(7) 0.0364(5) Uani 1 1 d . . .
H12 H 0.5690 0.8270 0.0684 0.044 Uiso 1 1 calc R . .
C13 C 0.6463(4) 0.67686(13) 0.06510(7) 0.0322(4) Uani 1 1 d . . .
C14 C 0.4982(5) 0.63842(17) 0.01634(7) 0.0484(5) Uani 1 1 d . . .
H14A H 0.6845 0.6219 -0.0061 0.073 Uiso 1 1 calc R . .
H14B H 0.3524 0.6874 0.0006 0.073 Uiso 1 1 calc R . .
H14C H 0.3617 0.5811 0.0230 0.073 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.232(2) . ?
O2 C7 1.268(2) . ?
O3 C8 1.2766(19) . ?
O3 H3 0.8200 . ?
O4 C8 1.249(2) . ?
O5 C9 1.314(2) . ?
O5 H5 0.8200 . ?
O6 C9 1.201(2) . ?
N1 C11 1.334(2) . ?
N1 N2 1.336(2) . ?
N1 H1 0.8600 . ?
N2 C13 1.328(2) . ?
N2 H2 0.8600 . ?
C1 C6 1.381(2) . ?
C1 C2 1.388(2) . ?
C1 C7 1.506(2) . ?
C2 C3 1.389(2) . ?
C2 H2A 0.9300 . ?
C3 C4 1.389(2) . ?
C3 C8 1.484(2) . ?
C4 C5 1.383(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.397(2) . ?
C5 C9 1.491(2) . ?
C6 H6 0.9300 . ?
C10 C11 1.484(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.370(3) . ?
C12 C13 1.383(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.483(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 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
C8 O3 H3 109.5 . . ?
C9 O5 H5 109.5 . . ?
C11 N1 N2 110.85(14) . . ?
C11 N1 H1 124.6 . . ?
N2 N1 H1 124.6 . . ?
C13 N2 N1 107.75(14) . . ?
C13 N2 H2 126.1 . . ?
N1 N2 H2 126.1 . . ?
C6 C1 C2 119.06(15) . . ?
C6 C1 C7 121.59(14) . . ?
C2 C1 C7 119.35(14) . . ?
C3 C2 C1 120.64(15) . . ?
C3 C2 H2A 119.7 . . ?
C1 C2 H2A 119.7 . . ?
C4 C3 C2 119.98(15) . . ?
C4 C3 C8 119.88(14) . . ?
C2 C3 C8 120.14(14) . . ?
C5 C4 C3 119.77(15) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 119.75(15) . . ?
C4 C5 C9 121.14(15) . . ?
C6 C5 C9 119.10(14) . . ?
C1 C6 C5 120.76(15) . . ?
C1 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
O1 C7 O2 124.00(16) . . ?
O1 C7 C1 120.90(15) . . ?
O2 C7 C1 115.09(14) . . ?
O4 C8 O3 123.42(15) . . ?
O4 C8 C3 119.94(14) . . ?
O3 C8 C3 116.63(15) . . ?
O6 C9 O5 123.85(15) . . ?
O6 C9 C5 122.67(16) . . ?
O5 C9 C5 113.48(14) . . ?
C11 C10 H10A 109.5 . . ?
C11 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C11 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 C12 106.24(16) . . ?
N1 C11 C10 122.19(17) . . ?
C12 C11 C10 131.57(17) . . ?
C11 C12 C13 107.19(16) . . ?
C11 C12 H12 126.4 . . ?
C13 C12 H12 126.4 . . ?
N2 C13 C12 107.97(16) . . ?
N2 C13 C14 121.38(17) . . ?
C12 C13 C14 130.65(17) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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
C11 N1 N2 C13 -0.2(2) . . . . ?
C6 C1 C2 C3 -0.5(2) . . . . ?
C7 C1 C2 C3 -179.65(16) . . . . ?
C1 C2 C3 C4 1.7(2) . . . . ?
C1 C2 C3 C8 -179.13(15) . . . . ?
C2 C3 C4 C5 -1.1(2) . . . . ?
C8 C3 C4 C5 179.67(15) . . . . ?
C3 C4 C5 C6 -0.6(2) . . . . ?
C3 C4 C5 C9 179.50(15) . . . . ?
C2 C1 C6 C5 -1.2(2) . . . . ?
C7 C1 C6 C5 177.92(15) . . . . ?
C4 C5 C6 C1 1.8(2) . . . . ?
C9 C5 C6 C1 -178.30(15) . . . . ?
C6 C1 C7 O1 0.8(3) . . . . ?
C2 C1 C7 O1 179.98(16) . . . . ?
C6 C1 C7 O2 -178.29(16) . . . . ?
C2 C1 C7 O2 0.9(2) . . . . ?
C4 C3 C8 O4 -6.4(3) . . . . ?
C2 C3 C8 O4 174.35(17) . . . . ?
C4 C3 C8 O3 174.33(16) . . . . ?
C2 C3 C8 O3 -4.9(2) . . . . ?
C4 C5 C9 O6 168.72(17) . . . . ?
C6 C5 C9 O6 -11.2(3) . . . . ?
C4 C5 C9 O5 -11.5(2) . . . . ?
C6 C5 C9 O5 168.54(16) . . . . ?
N2 N1 C11 C12 0.4(2) . . . . ?
N2 N1 C11 C10 179.87(16) . . . . ?
N1 C11 C12 C13 -0.4(2) . . . . ?
C10 C11 C12 C13 -179.81(19) . . . . ?
N1 N2 C13 C12 -0.04(19) . . . . ?
N1 N2 C13 C14 179.41(16) . . . . ?
C11 C12 C13 N2 0.3(2) . . . . ?
C11 C12 C13 C14 -179.10(18) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        26.75
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.057
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ups424kt
_database_code_depnum_ccdc_archive 'CCDC 1030332'
_audit_update_record             
;
2014-10-21 deposited with the CCDC.
2014-12-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8.83 H16.49 N2, C9 H6 O6, C9 H5 O6, 0.11(O) '
_chemical_formula_sum            'C26.83 H27.49 N2 O12.11'
_chemical_formula_weight         571.80

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'
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   10.122(2)
_cell_length_b                   10.636(2)
_cell_length_c                   14.713(3)
_cell_angle_alpha                94.212(11)
_cell_angle_beta                 105.650(11)
_cell_angle_gamma                104.860(11)
_cell_volume                     1456.8(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    569(2)
_cell_measurement_reflns_used    114
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      27.00

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.221
_exptl_crystal_size_mid          0.187
_exptl_crystal_size_min          0.157
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             598.8
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.977
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      569(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  'CCD area detector'
_diffrn_measurement_method       'phi omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            27518
_diffrn_reflns_av_R_equivalents  0.0472
_diffrn_reflns_av_sigmaI/netI    0.0420
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.50
_diffrn_reflns_theta_max         27.00
_reflns_number_total             6349
_reflns_number_gt                3627
_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)+(0.0000P)²+0.4983P] 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         6146
_refine_ls_number_parameters     375
_refine_ls_number_restraints     346
_refine_ls_R_factor_all          0.1109
_refine_ls_R_factor_gt           0.0641
_refine_ls_wR_factor_ref         0.1429
_refine_ls_wR_factor_gt          0.1309
_refine_ls_goodness_of_fit_ref   1.681
_refine_ls_restrained_S_all      1.654
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.2272(2) 0.53036(19) 0.50827(12) 0.0479(5) Uani 1 1 d U . .
O2 O 1.2028(2) 0.4076(2) 0.37176(14) 0.0575(6) Uani 1 1 d U . .
H2A H 1.2680 0.3849 0.4064 0.086 Uiso 1 1 calc R . .
O3 O 0.9330(2) 0.8259(2) 0.50801(13) 0.0556(6) Uani 1 1 d U . .
H3 H 0.9017 0.8808 0.5305 0.083 Uiso 1 1 calc R . .
O4 O 0.7916(2) 0.85767(19) 0.37202(13) 0.0515(5) Uani 1 1 d U . .
O5 O 0.7669(2) 0.6056(2) 0.06803(13) 0.0552(6) Uani 1 1 d U . .
O6 O 0.8679(3) 0.4429(2) 0.07545(13) 0.0689(7) Uani 1 1 d U . .
H6A H 0.8263 0.4271 0.0179 0.103 Uiso 1 1 calc R . .
O7 O 0.4194(2) 0.4270(2) 0.60490(13) 0.0553(6) Uani 1 1 d U . .
H7 H 0.3609 0.4558 0.5689 0.083 Uiso 1 1 calc R . .
O8 O 0.3928(2) 0.3026(2) 0.46915(13) 0.0554(6) Uani 1 1 d U . .
O9 O 0.7476(3) 0.3797(2) 0.90315(14) 0.0714(7) Uani 1 1 d U . .
O10 O 0.8722(2) 0.2365(2) 0.90346(14) 0.0684(7) Uani 1 1 d U . .
O11 O 0.8430(2) -0.01094(18) 0.60029(13) 0.0469(5) Uani 1 1 d U . .
O12 O 0.7060(2) 0.0263(2) 0.46462(12) 0.0494(5) Uani 1 1 d U . .
H12 H 0.7449 -0.0210 0.4416 0.074 Uiso 1 1 calc R . .
O1W O 0.547(3) 0.710(5) 0.107(2) 0.19(3) Uani 0.114(11) 1 d P . .
N1 N 0.8071(3) 0.7097(3) 0.91270(17) 0.0582(7) Uani 1 1 d U . .
H1 H 0.7695 0.6602 0.9482 0.070 Uiso 1 1 calc R . .
N2 N 0.9464(3) 0.7618(3) 0.92731(19) 0.0642(8) Uani 1 1 d U . .
H2B H 1.0130 0.7509 0.9738 0.077 Uiso 1 1 calc R . .
C1 C 1.0605(3) 0.5516(2) 0.36662(17) 0.0321(6) Uani 1 1 d U . .
C2 C 1.0007(3) 0.5160(2) 0.26835(17) 0.0354(6) Uani 1 1 d U . .
H2 H 1.0271 0.4527 0.2360 0.042 Uiso 1 1 calc R . .
C3 C 0.9017(3) 0.5747(2) 0.21850(17) 0.0347(6) Uani 1 1 d U . .
C4 C 0.8635(3) 0.6685(2) 0.26745(17) 0.0353(6) Uani 1 1 d U . .
H4 H 0.7983 0.7091 0.2341 0.042 Uiso 1 1 calc R . .
C5 C 0.9210(3) 0.7029(2) 0.36559(17) 0.0326(6) Uani 1 1 d U . .
C6 C 1.0204(3) 0.6443(2) 0.41531(17) 0.0328(6) Uani 1 1 d U . .
H6 H 1.0599 0.6674 0.4812 0.039 Uiso 1 1 calc R . .
C7 C 1.1707(3) 0.4930(2) 0.42023(18) 0.0346(6) Uani 1 1 d U . .
C8 C 0.8399(3) 0.5407(3) 0.11228(18) 0.0417(7) Uani 1 1 d U . .
C9 C 0.8781(3) 0.8026(3) 0.41742(18) 0.0361(6) Uani 1 1 d U . .
C10 C 0.5555(3) 0.2770(2) 0.61039(17) 0.0333(6) Uani 1 1 d U . .
C11 C 0.6135(3) 0.3089(3) 0.70879(18) 0.0368(6) Uani 1 1 d U . .
H11 H 0.5842 0.3688 0.7423 0.044 Uiso 1 1 calc R . .
C12 C 0.7150(3) 0.2519(3) 0.75745(17) 0.0357(6) Uani 1 1 d U . .
C13 C 0.7569(3) 0.1623(2) 0.70719(17) 0.0348(6) Uani 1 1 d U . .
H13 H 0.8232 0.1221 0.7397 0.042 Uiso 1 1 calc R . .
C14 C 0.7010(3) 0.1317(2) 0.60873(17) 0.0311(6) Uani 1 1 d U . .
C15 C 0.6000(3) 0.1894(2) 0.56019(17) 0.0335(6) Uani 1 1 d U . .
H15 H 0.5624 0.1692 0.4941 0.040 Uiso 1 1 calc R . .
C16 C 0.4490(3) 0.3390(3) 0.55722(19) 0.0375(6) Uani 1 1 d U . .
C17 C 0.7839(3) 0.2907(3) 0.86320(19) 0.0452(7) Uani 1 1 d U . .
C18 C 0.7533(3) 0.0423(2) 0.55503(18) 0.0345(6) Uani 1 1 d U . .
C19 C 1.1697(8) 1.0220(8) 0.9177(7) 0.276(6) Uani 1 1 d DU . .
H19A H 1.2720 1.0507 0.9316 0.414 Uiso 1 1 calc R . .
H19B H 1.1454 1.0136 0.9761 0.414 Uiso 1 1 calc R . .
H19C H 1.1293 1.0853 0.8861 0.414 Uiso 1 1 calc R . .
C20 C 1.1158(6) 0.9020(7) 0.8592(4) 0.1409(15) Uani 1 1 d DU . .
H20 H 1.1719 0.8496 0.8955 0.169 Uiso 1 1 calc R . .
C21 C 1.1393(6) 0.8841(6) 0.7696(4) 0.1409(15) Uani 1 1 d U . .
H21A H 1.0788 0.9218 0.7246 0.211 Uiso 1 1 calc R . .
H21B H 1.1174 0.7917 0.7477 0.211 Uiso 1 1 calc R . .
H21C H 1.2378 0.9265 0.7756 0.211 Uiso 1 1 calc R . .
C22 C 0.9677(4) 0.8329(3) 0.8601(2) 0.0646(6) Uani 1 1 d U . .
C23 C 0.8346(4) 0.8249(3) 0.8001(2) 0.0646(6) Uani 1 1 d U . .
H23 H 0.8159 0.8655 0.7461 0.077 Uiso 1 1 calc R . .
C24 C 0.7347(4) 0.7464(3) 0.8341(2) 0.0575(8) Uani 1 1 d U . .
C25 C 0.5759(5) 0.7043(6) 0.7973(4) 0.1223(16) Uani 1 1 d DU . .
H25 H 0.5557 0.6296 0.7475 0.147 Uiso 1 1 calc R . .
C26 C 0.5173(5) 0.7977(6) 0.7447(4) 0.147(2) Uani 1 1 d U . .
H26A H 0.4175 0.7575 0.7117 0.220 Uiso 1 1 calc R . .
H26B H 0.5675 0.8235 0.6991 0.220 Uiso 1 1 calc R . .
H26C H 0.5280 0.8740 0.7883 0.220 Uiso 1 1 calc R . .
C27 C 0.5075(5) 0.6477(7) 0.8618(4) 0.1223(16) Uani 0.831(9) 1 d PDU . .
H27A H 0.5163 0.7149 0.9121 0.183 Uiso 0.831(9) 1 calc PR . .
H27B H 0.5513 0.5832 0.8884 0.183 Uiso 0.831(9) 1 calc PR . .
H27C H 0.4079 0.6061 0.8289 0.183 Uiso 0.831(9) 1 calc PR . .


_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 C7 1.254(3) . ?
O2 C7 1.272(3) . ?
O2 H2A 0.8200 . ?
O3 C9 1.276(3) . ?
O3 H3 0.8200 . ?
O4 C9 1.249(3) . ?
O5 C8 1.231(3) . ?
O6 C8 1.267(3) . ?
O6 H6A 0.8200 . ?
O7 C16 1.272(3) . ?
O7 H7 0.8200 . ?
O8 C16 1.252(3) . ?
O9 C17 1.261(3) . ?
O10 C17 1.229(3) . ?
O11 C18 1.257(3) . ?
O12 C18 1.268(3) . ?
O12 H12 0.8200 . ?
N1 N2 1.326(4) . ?
N1 C24 1.334(3) . ?
N1 H1 0.8600 . ?
N2 C22 1.318(4) . ?
N2 H2B 0.8600 . ?
C1 C6 1.381(3) . ?
C1 C2 1.389(3) . ?
C1 C7 1.487(3) . ?
C2 C3 1.388(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.380(3) . ?
C3 C8 1.496(3) . ?
C4 C5 1.385(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.388(3) . ?
C5 C9 1.481(3) . ?
C6 H6 0.9300 . ?
C10 C15 1.382(3) . ?
C10 C11 1.387(3) . ?
C10 C16 1.481(3) . ?
C11 C12 1.386(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.382(3) . ?
C12 C17 1.500(3) . ?
C13 C14 1.385(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.387(3) . ?
C14 C18 1.477(3) . ?
C15 H15 0.9300 . ?
C19 C20 1.377(7) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.408(6) . ?
C20 C22 1.496(6) . ?
C20 H20 0.9800 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.375(5) . ?
C23 C24 1.369(5) . ?
C23 H23 0.9300 . ?
C24 C25 1.484(5) . ?
C25 C27 1.402(6) . ?
C25 C26 1.452(6) . ?
C25 H25 0.9800 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 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
C7 O2 H2A 109.5 . . ?
C9 O3 H3 109.5 . . ?
C8 O6 H6A 109.5 . . ?
C16 O7 H7 109.5 . . ?
C18 O12 H12 109.5 . . ?
N2 N1 C24 109.1(3) . . ?
N2 N1 H1 125.4 . . ?
C24 N1 H1 125.4 . . ?
C22 N2 N1 110.0(3) . . ?
C22 N2 H2B 125.0 . . ?
N1 N2 H2B 125.0 . . ?
C6 C1 C2 120.3(2) . . ?
C6 C1 C7 119.2(2) . . ?
C2 C1 C7 120.5(2) . . ?
C3 C2 C1 120.0(2) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C4 C3 C2 119.4(2) . . ?
C4 C3 C8 119.9(2) . . ?
C2 C3 C8 120.7(2) . . ?
C3 C4 C5 120.8(2) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C4 C5 C6 119.7(2) . . ?
C4 C5 C9 120.3(2) . . ?
C6 C5 C9 120.0(2) . . ?
C1 C6 C5 119.8(2) . . ?
C1 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
O1 C7 O2 124.2(2) . . ?
O1 C7 C1 119.4(2) . . ?
O2 C7 C1 116.5(2) . . ?
O5 C8 O6 125.3(2) . . ?
O5 C8 C3 119.7(2) . . ?
O6 C8 C3 115.0(2) . . ?
O4 C9 O3 123.9(2) . . ?
O4 C9 C5 119.7(2) . . ?
O3 C9 C5 116.4(2) . . ?
C15 C10 C11 120.1(2) . . ?
C15 C10 C16 119.0(2) . . ?
C11 C10 C16 120.8(2) . . ?
C12 C11 C10 120.2(2) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C13 C12 C11 119.5(2) . . ?
C13 C12 C17 119.8(2) . . ?
C11 C12 C17 120.7(2) . . ?
C12 C13 C14 120.5(2) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C13 C14 C15 119.9(2) . . ?
C13 C14 C18 120.1(2) . . ?
C15 C14 C18 120.0(2) . . ?
C10 C15 C14 119.8(2) . . ?
C10 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
O8 C16 O7 123.6(2) . . ?
O8 C16 C10 119.2(2) . . ?
O7 C16 C10 117.2(2) . . ?
O10 C17 O9 125.4(3) . . ?
O10 C17 C12 118.4(3) . . ?
O9 C17 C12 116.2(2) . . ?
O11 C18 O12 123.9(2) . . ?
O11 C18 C14 119.1(2) . . ?
O12 C18 C14 117.0(2) . . ?
C20 C19 H19A 109.5 . . ?
C20 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C20 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C19 C20 C21 121.9(6) . . ?
C19 C20 C22 111.6(6) . . ?
C21 C20 C22 114.3(5) . . ?
C19 C20 H20 101.7 . . ?
C21 C20 H20 101.7 . . ?
C22 C20 H20 101.7 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N2 C22 C23 106.7(3) . . ?
N2 C22 C20 121.0(4) . . ?
C23 C22 C20 132.3(4) . . ?
C24 C23 C22 107.6(3) . . ?
C24 C23 H23 126.2 . . ?
C22 C23 H23 126.2 . . ?
N1 C24 C23 106.6(3) . . ?
N1 C24 C25 122.9(3) . . ?
C23 C24 C25 130.5(3) . . ?
C27 C25 C26 117.3(5) . . ?
C27 C25 C24 114.4(4) . . ?
C26 C25 C24 113.6(4) . . ?
C27 C25 H25 103.0 . . ?
C26 C25 H25 103.0 . . ?
C24 C25 H25 103.0 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 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
C24 N1 N2 C22 0.3(4) . . . . ?
C6 C1 C2 C3 0.8(4) . . . . ?
C7 C1 C2 C3 -177.7(2) . . . . ?
C1 C2 C3 C4 0.0(4) . . . . ?
C1 C2 C3 C8 178.0(3) . . . . ?
C2 C3 C4 C5 -1.0(4) . . . . ?
C8 C3 C4 C5 -179.0(3) . . . . ?
C3 C4 C5 C6 1.2(4) . . . . ?
C3 C4 C5 C9 -179.4(2) . . . . ?
C2 C1 C6 C5 -0.6(4) . . . . ?
C7 C1 C6 C5 177.9(2) . . . . ?
C4 C5 C6 C1 -0.4(4) . . . . ?
C9 C5 C6 C1 -179.8(2) . . . . ?
C6 C1 C7 O1 -1.3(4) . . . . ?
C2 C1 C7 O1 177.2(3) . . . . ?
C6 C1 C7 O2 179.7(3) . . . . ?
C2 C1 C7 O2 -1.9(4) . . . . ?
C4 C3 C8 O5 7.3(4) . . . . ?
C2 C3 C8 O5 -170.6(3) . . . . ?
C4 C3 C8 O6 -171.9(3) . . . . ?
C2 C3 C8 O6 10.1(4) . . . . ?
C4 C5 C9 O4 -1.3(4) . . . . ?
C6 C5 C9 O4 178.1(3) . . . . ?
C4 C5 C9 O3 178.1(3) . . . . ?
C6 C5 C9 O3 -2.6(4) . . . . ?
C15 C10 C11 C12 -0.8(4) . . . . ?
C16 C10 C11 C12 -178.9(3) . . . . ?
C10 C11 C12 C13 -0.6(4) . . . . ?
C10 C11 C12 C17 176.9(3) . . . . ?
C11 C12 C13 C14 1.6(4) . . . . ?
C17 C12 C13 C14 -175.9(3) . . . . ?
C12 C13 C14 C15 -1.3(4) . . . . ?
C12 C13 C14 C18 176.0(2) . . . . ?
C11 C10 C15 C14 1.2(4) . . . . ?
C16 C10 C15 C14 179.2(2) . . . . ?
C13 C14 C15 C10 -0.1(4) . . . . ?
C18 C14 C15 C10 -177.4(2) . . . . ?
C15 C10 C16 O8 5.9(4) . . . . ?
C11 C10 C16 O8 -176.0(3) . . . . ?
C15 C10 C16 O7 -174.4(3) . . . . ?
C11 C10 C16 O7 3.7(4) . . . . ?
C13 C12 C17 O10 -3.3(4) . . . . ?
C11 C12 C17 O10 179.2(3) . . . . ?
C13 C12 C17 O9 175.2(3) . . . . ?
C11 C12 C17 O9 -2.3(4) . . . . ?
C13 C14 C18 O11 3.9(4) . . . . ?
C15 C14 C18 O11 -178.8(2) . . . . ?
C13 C14 C18 O12 -174.6(2) . . . . ?
C15 C14 C18 O12 2.7(4) . . . . ?
N1 N2 C22 C23 0.0(4) . . . . ?
N1 N2 C22 C20 -179.5(4) . . . . ?
C19 C20 C22 N2 -84.1(8) . . . . ?
C21 C20 C22 N2 132.5(5) . . . . ?
C19 C20 C22 C23 96.6(8) . . . . ?
C21 C20 C22 C23 -46.8(9) . . . . ?
N2 C22 C23 C24 -0.2(4) . . . . ?
C20 C22 C23 C24 179.2(5) . . . . ?
N2 N1 C24 C23 -0.4(4) . . . . ?
N2 N1 C24 C25 179.7(4) . . . . ?
C22 C23 C24 N1 0.4(4) . . . . ?
C22 C23 C24 C25 -179.7(4) . . . . ?
N1 C24 C25 C27 13.2(8) . . . . ?
C23 C24 C25 C27 -166.6(5) . . . . ?
N1 C24 C25 C26 151.6(4) . . . . ?
C23 C24 C25 C26 -28.2(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.968
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.968
_refine_diff_density_max         0.702
_refine_diff_density_min         -0.494
_refine_diff_density_rms         0.058
####################################################################### 
# 
# 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_ups475kt3_0m
_database_code_depnum_ccdc_archive 'CCDC 1030333'
_audit_update_record             
;
2014-10-21 deposited with the CCDC.
2014-12-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H6 O6, C9 H5 O6, C9.92 H19 N2, 0.06(O)'
_chemical_formula_sum            'C27.92 H30 N2 O12.06'
_chemical_formula_weight         586.54

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'
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   10.037(3)
_cell_length_b                   10.936(3)
_cell_length_c                   14.655(4)
_cell_angle_alpha                94.839(15)
_cell_angle_beta                 104.698(14)
_cell_angle_gamma                104.297(14)
_cell_volume                     1489.1(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    102
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      26.78

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616.0
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.975
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'

_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  'CCD area detector'
_diffrn_measurement_method       'phi omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25830
_diffrn_reflns_av_R_equivalents  0.0474
_diffrn_reflns_av_sigmaI/netI    0.0408
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.45
_diffrn_reflns_theta_max         25.00
_reflns_number_total             5233
_reflns_number_gt                3362
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker Kappa Apex'
_computing_cell_refinement       'Bruker Kappa Apex'
_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)+(0.1000P)²+0.7687P] 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         5233
_refine_ls_number_parameters     423
_refine_ls_number_restraints     384
_refine_ls_R_factor_all          0.0875
_refine_ls_R_factor_gt           0.0569
_refine_ls_wR_factor_ref         0.1837
_refine_ls_wR_factor_gt          0.1611
_refine_ls_goodness_of_fit_ref   0.973
_refine_ls_restrained_S_all      0.953
_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
O1W O 0.544(5) 0.218(5) 0.098(5) 0.12(3) Uani 0.060(9) 1 d P A 1
O1 O 0.7682(2) 0.10479(18) 0.06620(12) 0.0479(5) Uani 1 1 d U B 1
O2 O 0.8679(3) -0.0561(2) 0.07102(13) 0.0626(6) Uani 1 1 d U B 1
H2B H 0.8257 -0.0717 0.0138 0.094 Uiso 1 1 calc R B 1
O3 O 1.2264(2) 0.02832(18) 0.50515(12) 0.0474(5) Uani 1 1 d U B 1
O4 O 1.2021(2) -0.0935(2) 0.36854(14) 0.0570(6) Uani 1 1 d U B 1
H4A H 1.2535 -0.1271 0.4049 0.085 Uiso 1 1 calc R B 1
O5 O 0.7886(2) 0.35033(18) 0.37098(13) 0.0491(5) Uani 1 1 d U B 1
O6 O 0.9329(2) 0.3235(2) 0.50705(12) 0.0527(5) Uani 1 1 d U B 1
H6 H 0.8978 0.3744 0.5300 0.079 Uiso 1 1 calc R B 1
O7 O 0.7037(2) 0.52240(19) 0.45983(12) 0.0475(5) Uani 1 1 d U C 1
H7 H 0.7396 0.4722 0.4369 0.071 Uiso 1 1 calc R C 1
O8 O 0.8415(2) 0.48953(18) 0.59674(13) 0.0475(5) Uani 1 1 d U C 1
O9 O 0.3890(2) 0.7984(2) 0.46374(13) 0.0536(5) Uani 1 1 d U C 1
O10 O 0.4196(2) 0.92583(19) 0.59896(14) 0.0539(6) Uani 1 1 d U C 1
H10 H 0.3623 0.9546 0.5629 0.081 Uiso 1 1 calc R C 1
O11 O 0.7466(3) 0.8826(2) 0.89859(13) 0.0652(7) Uani 1 1 d U C 1
O12 O 0.8726(2) 0.7420(2) 0.89884(13) 0.0556(6) Uani 1 1 d U C 1
N1 N 0.0400(3) 0.7325(2) 0.07037(16) 0.0494(6) Uani 1 1 d U D 1
H1 H -0.0272 0.7433 0.0247 0.059 Uiso 1 1 calc R D 1
N2 N 0.1806(3) 0.7857(2) 0.08469(17) 0.0535(6) Uani 1 1 d U D 1
H2A H 0.2176 0.8353 0.0497 0.064 Uiso 1 1 calc R D 1
C1 C 0.6999(2) 0.6322(2) 0.60406(16) 0.0310(5) Uani 1 1 d U C 1
C2 C 0.5990(3) 0.6880(2) 0.55456(17) 0.0336(6) Uani 1 1 d U C 1
H2 H 0.5617 0.6665 0.4886 0.040 Uiso 1 1 calc R C 1
C3 C 0.5541(2) 0.7769(2) 0.60473(17) 0.0326(6) Uani 1 1 d U C 1
C4 C 0.6123(3) 0.8100(2) 0.70369(18) 0.0363(6) Uani 1 1 d U C 1
H4 H 0.5829 0.8697 0.7370 0.044 Uiso 1 1 calc R C 1
C5 C 0.7135(3) 0.7544(2) 0.75266(17) 0.0342(6) Uani 1 1 d U C 1
C6 C 0.7560(3) 0.6645(2) 0.70277(17) 0.0339(6) Uani 1 1 d U C 1
H6A H 0.8223 0.6257 0.7355 0.041 Uiso 1 1 calc R C 1
C7 C 0.7522(3) 0.5411(2) 0.55101(17) 0.0338(6) Uani 1 1 d U C 1
C8 C 0.4478(3) 0.8366(2) 0.55138(17) 0.0368(6) Uani 1 1 d U C 1
C9 C 0.7838(3) 0.7939(3) 0.85867(17) 0.0397(6) Uani 1 1 d U C 1
C10 C 0.9016(3) 0.0726(2) 0.21600(17) 0.0336(6) Uani 1 1 d U B 1
C11 C 0.8615(3) 0.1644(2) 0.26561(17) 0.0337(6) Uani 1 1 d U B 1
H11 H 0.7952 0.2033 0.2330 0.040 Uiso 1 1 calc R B 1
C12 C 0.9202(3) 0.1986(2) 0.36418(16) 0.0323(5) Uani 1 1 d U B 1
C13 C 1.0199(3) 0.1422(2) 0.41365(17) 0.0331(6) Uani 1 1 d U B 1
H13 H 1.0597 0.1660 0.4793 0.040 Uiso 1 1 calc R B 1
C14 C 1.0599(3) 0.0492(2) 0.36401(17) 0.0332(6) Uani 1 1 d U B 1
C15 C 1.0001(3) 0.0143(2) 0.26554(17) 0.0340(6) Uani 1 1 d U B 1
H15 H 1.0262 -0.0484 0.2328 0.041 Uiso 1 1 calc R B 1
C16 C 1.1696(3) -0.0087(2) 0.41685(17) 0.0344(6) Uani 1 1 d U B 1
C17 C 0.8396(3) 0.0403(2) 0.10932(17) 0.0374(6) Uani 1 1 d U B 1
C18 C 0.8763(3) 0.2979(2) 0.41598(17) 0.0348(6) Uani 1 1 d U B 1
C19 C 0.4763(5) 0.7027(6) 0.2494(4) 0.1176(18) Uani 1 1 d U E 1
H19A H 0.4622 0.6287 0.2041 0.176 Uiso 1 1 calc R E 1
H19B H 0.4293 0.6784 0.2972 0.176 Uiso 1 1 calc R E 1
H19C H 0.5771 0.7399 0.2792 0.176 Uiso 1 1 calc R E 1
C20 C 0.4850(6) 0.8727(8) 0.1453(6) 0.120(4) Uani 0.757(13) 1 d PU E 1
H20A H 0.4459 0.9437 0.1351 0.180 Uiso 1 1 calc R . .
H20B H 0.4721 0.8231 0.0849 0.180 Uiso 1 1 calc R . .
H20C H 0.5855 0.9036 0.1784 0.180 Uiso 1 1 calc R . .
C20' C 0.4702(19) 0.730(3) 0.0840(13) 0.123(12) Uani 0.243(13) 1 d PU E 2
C21 C 0.4153(4) 0.7971(5) 0.1996(4) 0.1142(18) Uani 1 1 d U . .
H21 H 0.4261 0.8611 0.2540 0.137 Uiso 1 1 calc R E 1
C22 C 0.2543(3) 0.7491(3) 0.1623(2) 0.0618(9) Uani 1 1 d U D .
C23 C 0.1553(4) 0.6697(3) 0.1961(2) 0.0617(9) Uani 1 1 d U . .
H23 H 0.1756 0.6291 0.2491 0.074 Uiso 1 1 calc R E .
C24 C 0.0196(3) 0.6604(3) 0.1375(2) 0.0489(7) Uani 1 1 d U D .
C25 C -0.1274(4) 0.5860(3) 0.1409(3) 0.0663(9) Uani 1 1 d U . .
C26 C -0.1237(19) 0.4509(17) 0.1605(11) 0.074(4) Uani 0.332(15) 1 d PU E 1
H26A H -0.0836 0.4133 0.1162 0.111 Uiso 1 1 calc R . .
H26B H -0.2194 0.3993 0.1530 0.111 Uiso 1 1 calc R . .
H26C H -0.0657 0.4555 0.2245 0.111 Uiso 1 1 calc R . .
C26' C -0.1455(18) 0.4493(13) 0.1137(17) 0.181(7) Uani 0.668(15) 1 d PU E 2
C27 C -0.1492(6) 0.6288(6) 0.2351(4) 0.131(3) Uani 0.920(14) 1 d PU E .
H27A H -0.2443 0.5853 0.2361 0.197 Uiso 1 1 calc R . .
H27B H -0.1370 0.7193 0.2431 0.197 Uiso 1 1 calc R . .
H27C H -0.0803 0.6091 0.2861 0.197 Uiso 1 1 calc R . .
C28 C -0.2446(13) 0.6222(13) 0.0808(9) 0.0663(9) Uani 0.332(15) 1 d PU E 1
H28A H -0.2313 0.6270 0.0185 0.099 Uiso 1 1 calc R . .
H28B H -0.2473 0.7041 0.1084 0.099 Uiso 1 1 calc R . .
H28C H -0.3333 0.5597 0.0756 0.099 Uiso 1 1 calc R . .
C28' C -0.2361(13) 0.5510(19) 0.0409(10) 0.184(8) Uani 0.668(15) 1 d PU E 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 C17 1.227(3) . ?
O2 C17 1.279(3) . ?
O2 H2B 0.8200 . ?
O3 C16 1.260(3) . ?
O4 C16 1.274(3) . ?
O4 H4A 0.8200 . ?
O5 C18 1.248(3) . ?
O6 C18 1.287(3) . ?
O6 H6 0.8200 . ?
O7 C7 1.280(3) . ?
O7 H7 0.8200 . ?
O8 C7 1.256(3) . ?
O9 C8 1.255(3) . ?
O10 C8 1.281(3) . ?
O10 H10 0.8200 . ?
O11 C9 1.271(3) . ?
O12 C9 1.226(3) . ?
N1 C24 1.336(4) . ?
N1 N2 1.341(3) . ?
N1 H1 0.8600 . ?
N2 C22 1.340(4) . ?
N2 H2A 0.8600 . ?
C1 C2 1.390(3) . ?
C1 C6 1.392(3) . ?
C1 C7 1.485(3) . ?
C2 C3 1.397(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.397(3) . ?
C3 C8 1.478(3) . ?
C4 C5 1.388(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.389(3) . ?
C5 C9 1.509(3) . ?
C6 H6A 0.9300 . ?
C10 C11 1.387(3) . ?
C10 C15 1.393(3) . ?
C10 C17 1.504(3) . ?
C11 C12 1.393(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.385(3) . ?
C12 C18 1.489(3) . ?
C13 C14 1.397(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.394(3) . ?
C14 C16 1.485(3) . ?
C15 H15 0.9300 . ?
C19 C21 1.479(6) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.383(7) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C22 1.507(5) . ?
C21 H21 0.9800 . ?
C22 C23 1.373(5) . ?
C23 C24 1.387(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.514(5) . ?
C25 C28 1.442(11) . ?
C25 C27 1.505(6) . ?
C25 C26 1.536(17) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 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
C24 N1 N2 110.0(2) . . ?
C24 N1 H1 125.0 . . ?
N2 N1 H1 125.0 . . ?
C22 N2 N1 109.1(2) . . ?
C22 N2 H2A 125.5 . . ?
N1 N2 H2A 125.5 . . ?
C2 C1 C6 120.3(2) . . ?
C2 C1 C7 119.9(2) . . ?
C6 C1 C7 119.7(2) . . ?
C1 C2 C3 119.5(2) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C4 C3 C2 119.8(2) . . ?
C4 C3 C8 121.1(2) . . ?
C2 C3 C8 119.1(2) . . ?
C5 C4 C3 120.5(2) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 119.5(2) . . ?
C4 C5 C9 121.4(2) . . ?
C6 C5 C9 119.0(2) . . ?
C5 C6 C1 120.3(2) . . ?
C5 C6 H6A 119.8 . . ?
C1 C6 H6A 119.8 . . ?
O8 C7 O7 124.2(2) . . ?
O8 C7 C1 119.2(2) . . ?
O7 C7 C1 116.5(2) . . ?
O9 C8 O10 123.2(2) . . ?
O9 C8 C3 119.9(2) . . ?
O10 C8 C3 116.9(2) . . ?
O12 C9 O11 125.3(2) . . ?
O12 C9 C5 119.1(2) . . ?
O11 C9 C5 115.6(2) . . ?
C11 C10 C15 119.5(2) . . ?
C11 C10 C17 119.1(2) . . ?
C15 C10 C17 121.4(2) . . ?
C10 C11 C12 120.2(2) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C13 C12 C11 120.6(2) . . ?
C13 C12 C18 120.1(2) . . ?
C11 C12 C18 119.3(2) . . ?
C12 C13 C14 119.4(2) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 H13 120.3 . . ?
C15 C14 C13 120.0(2) . . ?
C15 C14 C16 120.7(2) . . ?
C13 C14 C16 119.3(2) . . ?
C10 C15 C14 120.3(2) . . ?
C10 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
O3 C16 O4 123.5(2) . . ?
O3 C16 C14 119.5(2) . . ?
O4 C16 C14 116.9(2) . . ?
O1 C17 O2 125.3(2) . . ?
O1 C17 C10 119.9(2) . . ?
O2 C17 C10 114.7(2) . . ?
O5 C18 O6 123.9(2) . . ?
O5 C18 C12 120.0(2) . . ?
O6 C18 C12 116.2(2) . . ?
C21 C19 H19A 109.5 . . ?
C21 C19 H19B 109.5 . . ?
C21 C19 H19C 109.5 . . ?
C21 C20 H20A 109.5 . . ?
C21 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C21 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C20 C21 C19 121.8(5) . . ?
C20 C21 C22 116.7(4) . . ?
C19 C21 C22 111.3(4) . . ?
C20 C21 H21 100.7 . . ?
C19 C21 H21 100.7 . . ?
C22 C21 H21 100.7 . . ?
N2 C22 C23 106.7(3) . . ?
N2 C22 C21 122.0(3) . . ?
C23 C22 C21 131.3(3) . . ?
C22 C23 C24 108.2(3) . . ?
C22 C23 H23 125.9 . . ?
C24 C23 H23 125.9 . . ?
N1 C24 C23 106.0(3) . . ?
N1 C24 C25 123.2(3) . . ?
C23 C24 C25 130.9(3) . . ?
C28 C25 C27 96.9(6) . . ?
C28 C25 C24 114.3(6) . . ?
C27 C25 C24 109.2(3) . . ?
C28 C25 C26 127.2(9) . . ?
C27 C25 C26 95.6(7) . . ?
C24 C25 C26 109.2(7) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C25 C28 H28A 109.5 . . ?
C25 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C25 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 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
C24 N1 N2 C22 -0.4(3) . . . . ?
C6 C1 C2 C3 -0.1(4) . . . . ?
C7 C1 C2 C3 -177.8(2) . . . . ?
C1 C2 C3 C4 0.9(4) . . . . ?
C1 C2 C3 C8 179.5(2) . . . . ?
C2 C3 C4 C5 -0.6(4) . . . . ?
C8 C3 C4 C5 -179.1(2) . . . . ?
C3 C4 C5 C6 -0.6(4) . . . . ?
C3 C4 C5 C9 176.6(2) . . . . ?
C4 C5 C6 C1 1.4(4) . . . . ?
C9 C5 C6 C1 -175.9(2) . . . . ?
C2 C1 C6 C5 -1.0(4) . . . . ?
C7 C1 C6 C5 176.7(2) . . . . ?
C2 C1 C7 O8 -178.7(2) . . . . ?
C6 C1 C7 O8 3.6(4) . . . . ?
C2 C1 C7 O7 2.5(3) . . . . ?
C6 C1 C7 O7 -175.2(2) . . . . ?
C4 C3 C8 O9 -174.6(2) . . . . ?
C2 C3 C8 O9 6.9(4) . . . . ?
C4 C3 C8 O10 4.8(4) . . . . ?
C2 C3 C8 O10 -173.8(2) . . . . ?
C4 C5 C9 O12 179.9(3) . . . . ?
C6 C5 C9 O12 -2.8(4) . . . . ?
C4 C5 C9 O11 -1.7(4) . . . . ?
C6 C5 C9 O11 175.5(2) . . . . ?
C15 C10 C11 C12 0.5(4) . . . . ?
C17 C10 C11 C12 -178.3(2) . . . . ?
C10 C11 C12 C13 0.5(4) . . . . ?
C10 C11 C12 C18 179.6(2) . . . . ?
C11 C12 C13 C14 -0.8(4) . . . . ?
C18 C12 C13 C14 -180.0(2) . . . . ?
C12 C13 C14 C15 0.2(4) . . . . ?
C12 C13 C14 C16 178.4(2) . . . . ?
C11 C10 C15 C14 -1.1(4) . . . . ?
C17 C10 C15 C14 177.7(2) . . . . ?
C13 C14 C15 C10 0.7(4) . . . . ?
C16 C14 C15 C10 -177.5(2) . . . . ?
C15 C14 C16 O3 177.1(2) . . . . ?
C13 C14 C16 O3 -1.1(4) . . . . ?
C15 C14 C16 O4 -2.1(4) . . . . ?
C13 C14 C16 O4 179.7(2) . . . . ?
C11 C10 C17 O1 8.4(4) . . . . ?
C15 C10 C17 O1 -170.3(2) . . . . ?
C11 C10 C17 O2 -171.5(2) . . . . ?
C15 C10 C17 O2 9.7(4) . . . . ?
C13 C12 C18 O5 178.6(2) . . . . ?
C11 C12 C18 O5 -0.5(4) . . . . ?
C13 C12 C18 O6 -1.9(4) . . . . ?
C11 C12 C18 O6 179.0(2) . . . . ?
N1 N2 C22 C23 0.6(4) . . . . ?
N1 N2 C22 C21 -177.6(4) . . . . ?
C20 C21 C22 N2 -5.2(8) . . . . ?
C19 C21 C22 N2 -151.3(4) . . . . ?
C20 C21 C22 C23 177.1(6) . . . . ?
C19 C21 C22 C23 31.0(7) . . . . ?
N2 C22 C23 C24 -0.7(4) . . . . ?
C21 C22 C23 C24 177.3(5) . . . . ?
N2 N1 C24 C23 -0.1(3) . . . . ?
N2 N1 C24 C25 -179.4(3) . . . . ?
C22 C23 C24 N1 0.5(4) . . . . ?
C22 C23 C24 C25 179.7(3) . . . . ?
N1 C24 C25 C28 -14.1(7) . . . . ?
C23 C24 C25 C28 166.8(7) . . . . ?
N1 C24 C25 C27 -121.5(4) . . . . ?
C23 C24 C25 C27 59.4(5) . . . . ?
N1 C24 C25 C26 135.2(7) . . . . ?
C23 C24 C25 C26 -43.9(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.444
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.059
####################################################################### 
# 
# 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_ups481kt_8
_database_code_depnum_ccdc_archive 'CCDC 1030334'
_audit_update_record             
;
2014-10-21 deposited with the CCDC.
2014-12-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H10 N2, C9 H6 O6'
_chemical_formula_sum            'C19 H16 N2 O6'
_chemical_formula_weight         368.34

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   9.525(3)
_cell_length_b                   27.883(9)
_cell_length_c                   13.755(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.856(16)
_cell_angle_gamma                90.00
_cell_volume                     3477.2(19)
_cell_formula_units_Z            8
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    108
_cell_measurement_theta_min      2.78
_cell_measurement_theta_max      28.45

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1536.0
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.976
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'


_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      273(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  'CCD area detector'
_diffrn_measurement_method       'phi omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24658
_diffrn_reflns_av_R_equivalents  0.0609
_diffrn_reflns_av_sigmaI/netI    0.0729
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.46
_diffrn_reflns_theta_max         25.00
_reflns_number_total             6129
_reflns_number_gt                3321
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker Kappa Apex'
_computing_cell_refinement       'Bruker Kappa Apex'
_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)+(0.1000P)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    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0094(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6129
_refine_ls_number_parameters     496
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1193
_refine_ls_R_factor_gt           0.0594
_refine_ls_wR_factor_ref         0.1713
_refine_ls_wR_factor_gt          0.1354
_refine_ls_goodness_of_fit_ref   0.940
_refine_ls_restrained_S_all      0.940
_refine_ls_shift/su_max          0.009
_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 0.0200(2) 0.31316(7) 0.46340(17) 0.0503(6) Uani 1 1 d . . .
H1 H -0.0080 0.3003 0.5078 0.075 Uiso 1 1 calc R . .
O2 O 0.0727(3) 0.23830(7) 0.43298(17) 0.0568(7) Uani 1 1 d . . .
O3 O 0.3139(2) 0.20919(7) 0.17427(16) 0.0470(6) Uani 1 1 d . . .
H3 H 0.3457 0.1923 0.1370 0.070 Uiso 1 1 calc R . .
O4 O 0.4168(2) 0.26683(7) 0.10781(16) 0.0516(6) Uani 1 1 d . . .
O5 O 0.3489(2) 0.43634(7) 0.21838(16) 0.0501(6) Uani 1 1 d . . .
O6 O 0.1881(2) 0.44736(7) 0.30579(17) 0.0514(6) Uani 1 1 d . . .
H6 H 0.2103 0.4755 0.3008 0.077 Uiso 1 1 calc R . .
O7 O 0.5277(3) 0.17452(7) 0.48839(16) 0.0500(6) Uani 1 1 d . . .
H7 H 0.4928 0.1904 0.5255 0.075 Uiso 1 1 calc R . .
O8 O 0.5756(3) 0.24643(8) 0.43751(18) 0.0664(7) Uani 1 1 d . . .
O9 O 0.7931(2) 0.04045(7) 0.21263(17) 0.0578(7) Uani 1 1 d . . .
O10 O 0.6668(3) 0.03071(7) 0.32419(17) 0.0528(6) Uani 1 1 d . . .
H10 H 0.6654 0.0029 0.3047 0.079 Uiso 1 1 calc R . .
O11 O 0.8224(3) 0.26522(7) 0.18424(16) 0.0513(6) Uani 1 1 d . . .
H11 H 0.8574 0.2809 0.1467 0.077 Uiso 1 1 calc R . .
O12 O 0.9070(3) 0.20349(8) 0.11554(17) 0.0576(7) Uani 1 1 d . . .
N1 N -0.0991(3) 0.33570(8) 0.08818(17) 0.0379(6) Uani 1 1 d . . .
N2 N -0.0097(2) 0.34261(8) 0.02946(17) 0.0356(6) Uani 1 1 d . . .
H2 H 0.0252 0.3196 0.0020 0.043 Uiso 1 1 calc R . .
N3 N 0.5022(3) 0.16798(8) 0.01428(17) 0.0375(6) Uani 1 1 d . . .
H3A H 0.5198 0.1981 0.0106 0.045 Uiso 1 1 calc R . .
N4 N 0.4073(3) 0.15054(8) 0.06084(17) 0.0352(6) Uani 1 1 d . . .
C1 C 0.2119(3) 0.26996(10) 0.2906(2) 0.0320(7) Uani 1 1 d . . .
H1B H 0.2015 0.2370 0.2969 0.038 Uiso 1 1 calc R . .
C2 C 0.2860(3) 0.28733(9) 0.22548(19) 0.0288(7) Uani 1 1 d . . .
C3 C 0.3035(3) 0.33664(10) 0.2176(2) 0.0337(7) Uani 1 1 d . . .
H3B H 0.3545 0.3486 0.1750 0.040 Uiso 1 1 calc R . .
C4 C 0.2446(3) 0.36806(10) 0.2734(2) 0.0320(7) Uani 1 1 d . . .
C5 C 0.1683(3) 0.35049(9) 0.3371(2) 0.0317(7) Uani 1 1 d . . .
H5 H 0.1276 0.3717 0.3733 0.038 Uiso 1 1 calc R . .
C6 C 0.1526(3) 0.30125(9) 0.3470(2) 0.0295(7) Uani 1 1 d . . .
C7 C 0.0788(3) 0.28067(11) 0.4180(2) 0.0343(7) Uani 1 1 d . . .
C8 C 0.3454(3) 0.25402(10) 0.1629(2) 0.0337(7) Uani 1 1 d . . .
C9 C 0.2624(3) 0.42061(10) 0.2654(2) 0.0336(7) Uani 1 1 d . . .
C10 C 0.7235(3) 0.10969(9) 0.2861(2) 0.0314(7) Uani 1 1 d . . .
C11 C 0.6564(3) 0.12972(9) 0.3533(2) 0.0333(7) Uani 1 1 d . . .
H11A H 0.6160 0.1100 0.3923 0.040 Uiso 1 1 calc R . .
C12 C 0.6497(3) 0.17920(10) 0.3620(2) 0.0322(7) Uani 1 1 d . . .
C13 C 0.7102(3) 0.20815(10) 0.3028(2) 0.0340(7) Uani 1 1 d . . .
H13 H 0.7044 0.2413 0.3078 0.041 Uiso 1 1 calc R . .
C14 C 0.7790(3) 0.18864(10) 0.2363(2) 0.0300(7) Uani 1 1 d . . .
C15 C 0.7857(3) 0.13926(10) 0.2286(2) 0.0341(7) Uani 1 1 d . . .
H15 H 0.8321 0.1257 0.1848 0.041 Uiso 1 1 calc R . .
C16 C 0.7288(3) 0.05699(10) 0.2743(2) 0.0359(7) Uani 1 1 d . . .
C17 C 0.5810(3) 0.20357(11) 0.4322(2) 0.0375(7) Uani 1 1 d . . .
C18 C 0.8426(3) 0.21973(10) 0.1721(2) 0.0363(7) Uani 1 1 d . . .
C19 C -0.2239(4) 0.38648(13) 0.1827(3) 0.0650(11) Uani 1 1 d . . .
H19A H -0.2282 0.3572 0.2182 0.098 Uiso 1 1 calc R . .
H19B H -0.3214 0.3953 0.1416 0.098 Uiso 1 1 calc R . .
H19C H -0.1835 0.4114 0.2314 0.098 Uiso 1 1 calc R . .
C20 C -0.1282(3) 0.37957(11) 0.1158(2) 0.0409(8) Uani 1 1 d . . .
C21 C -0.0576(3) 0.41356(10) 0.0737(2) 0.0408(8) Uani 1 1 d . . .
H21 H -0.0612 0.4466 0.0812 0.049 Uiso 1 1 calc R . .
C22 C 0.0188(3) 0.38925(10) 0.0188(2) 0.0339(7) Uani 1 1 d . . .
C23 C 0.1177(3) 0.40584(10) -0.0377(2) 0.0369(7) Uani 1 1 d . . .
C24 C 0.1728(4) 0.45221(11) -0.0225(2) 0.0521(9) Uani 1 1 d . . .
H24 H 0.1423 0.4728 0.0203 0.063 Uiso 1 1 calc R . .
C25 C 0.2721(4) 0.46826(13) -0.0700(3) 0.0664(11) Uani 1 1 d . . .
H25 H 0.3086 0.4994 -0.0586 0.080 Uiso 1 1 calc R . .
C26 C 0.3173(4) 0.43848(15) -0.1341(3) 0.0686(11) Uani 1 1 d . . .
H26 H 0.3843 0.4493 -0.1660 0.082 Uiso 1 1 calc R . .
C27 C 0.2631(4) 0.39269(14) -0.1508(3) 0.0623(10) Uani 1 1 d . . .
H27 H 0.2934 0.3724 -0.1942 0.075 Uiso 1 1 calc R . .
C28 C 0.1632(4) 0.37654(12) -0.1032(2) 0.0507(9) Uani 1 1 d . . .
H28 H 0.1263 0.3455 -0.1155 0.061 Uiso 1 1 calc R . .
C29 C 0.6695(4) 0.14419(12) -0.0855(3) 0.0582(10) Uani 1 1 d . . .
H29A H 0.6945 0.1776 -0.0794 0.087 Uiso 1 1 calc R . .
H29B H 0.6230 0.1364 -0.1560 0.087 Uiso 1 1 calc R . .
H29C H 0.7576 0.1254 -0.0593 0.087 Uiso 1 1 calc R . .
C30 C 0.5661(3) 0.13354(11) -0.0256(2) 0.0388(8) Uani 1 1 d . . .
C31 C 0.5117(3) 0.09132(11) -0.0017(2) 0.0403(8) Uani 1 1 d . . .
H31 H 0.5363 0.0607 -0.0175 0.048 Uiso 1 1 calc R . .
C32 C 0.4131(3) 0.10282(10) 0.0508(2) 0.0334(7) Uani 1 1 d . . .
C33 C 0.3147(3) 0.07022(10) 0.0843(2) 0.0374(8) Uani 1 1 d . . .
C34 C 0.3559(4) 0.02306(11) 0.1080(2) 0.0536(9) Uani 1 1 d . . .
H34 H 0.4481 0.0127 0.1067 0.064 Uiso 1 1 calc R . .
C35 C 0.2630(5) -0.00866(13) 0.1335(3) 0.0726(12) Uani 1 1 d . . .
H35 H 0.2932 -0.0402 0.1499 0.087 Uiso 1 1 calc R . .
C36 C 0.1260(5) 0.00562(14) 0.1349(3) 0.0739(12) Uani 1 1 d . . .
H36 H 0.0626 -0.0162 0.1510 0.089 Uiso 1 1 calc R . .
C37 C 0.0831(4) 0.05241(14) 0.1126(3) 0.0655(11) Uani 1 1 d . . .
H37 H -0.0094 0.0624 0.1140 0.079 Uiso 1 1 calc R . .
C38 C 0.1771(4) 0.08463(11) 0.0880(2) 0.0491(9) Uani 1 1 d . . .
H38 H 0.1478 0.1163 0.0738 0.059 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.319(3) . ?
O1 H1 0.8200 . ?
O2 C7 1.204(3) . ?
O3 C8 1.306(3) . ?
O3 H3 0.8200 . ?
O4 C8 1.217(3) . ?
O5 C9 1.271(3) . ?
O6 C9 1.268(3) . ?
O6 H6 0.8200 . ?
O7 C17 1.323(3) . ?
O7 H7 0.8200 . ?
O8 C17 1.199(3) . ?
O9 C16 1.274(3) . ?
O10 C16 1.268(3) . ?
O10 H10 0.8200 . ?
O11 C18 1.301(3) . ?
O11 H11 0.8200 . ?
O12 C18 1.216(3) . ?
N1 C20 1.335(4) . ?
N1 N2 1.356(3) . ?
N2 C22 1.346(3) . ?
N2 H2 0.8600 . ?
N3 C30 1.341(3) . ?
N3 N4 1.349(3) . ?
N3 H3A 0.8600 . ?
N4 C32 1.340(3) . ?
C1 C2 1.387(4) . ?
C1 C6 1.396(4) . ?
C1 H1B 0.9300 . ?
C2 C3 1.393(4) . ?
C2 C8 1.491(4) . ?
C3 C4 1.392(4) . ?
C3 H3B 0.9300 . ?
C4 C5 1.387(4) . ?
C4 C9 1.483(4) . ?
C5 C6 1.392(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.483(4) . ?
C10 C11 1.392(4) . ?
C10 C15 1.394(4) . ?
C10 C16 1.481(4) . ?
C11 C12 1.388(4) . ?
C11 H11A 0.9300 . ?
C12 C13 1.391(4) . ?
C12 C17 1.487(4) . ?
C13 C14 1.388(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.384(4) . ?
C14 C18 1.492(4) . ?
C15 H15 0.9300 . ?
C19 C20 1.492(4) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.387(4) . ?
C21 C22 1.378(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.467(4) . ?
C23 C28 1.381(4) . ?
C23 C24 1.387(4) . ?
C24 C25 1.379(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.372(5) . ?
C25 H25 0.9300 . ?
C26 C27 1.370(5) . ?
C26 H26 0.9300 . ?
C27 C28 1.385(4) . ?
C27 H27 0.9300 . ?
C28 H28 0.9300 . ?
C29 C30 1.495(4) . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 C31 1.366(4) . ?
C31 C32 1.386(4) . ?
C31 H31 0.9300 . ?
C32 C33 1.477(4) . ?
C33 C34 1.383(4) . ?
C33 C38 1.387(4) . ?
C34 C35 1.371(4) . ?
C34 H34 0.9300 . ?
C35 C36 1.370(5) . ?
C35 H35 0.9300 . ?
C36 C37 1.374(5) . ?
C36 H36 0.9300 . ?
C37 C38 1.382(4) . ?
C37 H37 0.9300 . ?
C38 H38 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
C7 O1 H1 109.5 . . ?
C8 O3 H3 109.5 . . ?
C9 O6 H6 109.5 . . ?
C17 O7 H7 109.5 . . ?
C16 O10 H10 109.5 . . ?
C18 O11 H11 109.5 . . ?
C20 N1 N2 105.2(2) . . ?
C22 N2 N1 112.8(2) . . ?
C22 N2 H2 123.6 . . ?
N1 N2 H2 123.6 . . ?
C30 N3 N4 113.0(2) . . ?
C30 N3 H3A 123.5 . . ?
N4 N3 H3A 123.5 . . ?
C32 N4 N3 104.7(2) . . ?
C2 C1 C6 120.9(2) . . ?
C2 C1 H1B 119.6 . . ?
C6 C1 H1B 119.6 . . ?
C1 C2 C3 119.4(2) . . ?
C1 C2 C8 120.9(2) . . ?
C3 C2 C8 119.6(2) . . ?
C4 C3 C2 120.0(3) . . ?
C4 C3 H3B 120.0 . . ?
C2 C3 H3B 120.0 . . ?
C5 C4 C3 120.2(3) . . ?
C5 C4 C9 119.3(3) . . ?
C3 C4 C9 120.4(3) . . ?
C4 C5 C6 120.2(3) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C1 119.2(2) . . ?
C5 C6 C7 122.2(2) . . ?
C1 C6 C7 118.6(2) . . ?
O2 C7 O1 122.9(3) . . ?
O2 C7 C6 123.4(3) . . ?
O1 C7 C6 113.7(2) . . ?
O4 C8 O3 123.2(3) . . ?
O4 C8 C2 124.1(3) . . ?
O3 C8 C2 112.7(2) . . ?
O6 C9 O5 123.8(3) . . ?
O6 C9 C4 117.2(3) . . ?
O5 C9 C4 119.1(3) . . ?
C11 C10 C15 120.0(2) . . ?
C11 C10 C16 120.6(3) . . ?
C15 C10 C16 119.3(3) . . ?
C12 C11 C10 119.9(3) . . ?
C12 C11 H11A 120.1 . . ?
C10 C11 H11A 120.1 . . ?
C13 C12 C11 119.2(3) . . ?
C13 C12 C17 117.3(2) . . ?
C11 C12 C17 123.4(3) . . ?
C12 C13 C14 121.5(3) . . ?
C12 C13 H13 119.3 . . ?
C14 C13 H13 119.3 . . ?
C15 C14 C13 118.8(3) . . ?
C15 C14 C18 119.8(2) . . ?
C13 C14 C18 121.4(2) . . ?
C14 C15 C10 120.5(3) . . ?
C14 C15 H15 119.7 . . ?
C10 C15 H15 119.7 . . ?
O10 C16 O9 123.4(3) . . ?
O10 C16 C10 118.5(3) . . ?
O9 C16 C10 118.2(3) . . ?
O8 C17 O7 122.9(3) . . ?
O8 C17 C12 122.0(3) . . ?
O7 C17 C12 115.1(2) . . ?
O12 C18 O11 124.6(3) . . ?
O12 C18 C14 122.6(3) . . ?
O11 C18 C14 112.8(2) . . ?
C20 C19 H19A 109.5 . . ?
C20 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C20 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N1 C20 C21 109.7(3) . . ?
N1 C20 C19 120.9(3) . . ?
C21 C20 C19 129.4(3) . . ?
C22 C21 C20 107.4(3) . . ?
C22 C21 H21 126.3 . . ?
C20 C21 H21 126.3 . . ?
N2 C22 C21 104.9(2) . . ?
N2 C22 C23 123.1(3) . . ?
C21 C22 C23 131.9(3) . . ?
C28 C23 C24 118.0(3) . . ?
C28 C23 C22 122.7(3) . . ?
C24 C23 C22 119.3(3) . . ?
C25 C24 C23 121.0(3) . . ?
C25 C24 H24 119.5 . . ?
C23 C24 H24 119.5 . . ?
C26 C25 C24 120.2(3) . . ?
C26 C25 H25 119.9 . . ?
C24 C25 H25 119.9 . . ?
C25 C26 C27 119.7(3) . . ?
C25 C26 H26 120.1 . . ?
C27 C26 H26 120.1 . . ?
C26 C27 C28 120.1(4) . . ?
C26 C27 H27 120.0 . . ?
C28 C27 H27 120.0 . . ?
C23 C28 C27 121.0(3) . . ?
C23 C28 H28 119.5 . . ?
C27 C28 H28 119.5 . . ?
C30 C29 H29A 109.5 . . ?
C30 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C30 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
N3 C30 C31 105.4(3) . . ?
N3 C30 C29 122.8(3) . . ?
C31 C30 C29 131.8(3) . . ?
C30 C31 C32 107.1(3) . . ?
C30 C31 H31 126.5 . . ?
C32 C31 H31 126.5 . . ?
N4 C32 C31 109.8(3) . . ?
N4 C32 C33 121.9(3) . . ?
C31 C32 C33 128.0(3) . . ?
C34 C33 C38 118.0(3) . . ?
C34 C33 C32 119.9(3) . . ?
C38 C33 C32 122.0(3) . . ?
C35 C34 C33 121.0(3) . . ?
C35 C34 H34 119.5 . . ?
C33 C34 H34 119.5 . . ?
C36 C35 C34 120.6(3) . . ?
C36 C35 H35 119.7 . . ?
C34 C35 H35 119.7 . . ?
C35 C36 C37 119.5(3) . . ?
C35 C36 H36 120.3 . . ?
C37 C36 H36 120.3 . . ?
C36 C37 C38 120.1(3) . . ?
C36 C37 H37 120.0 . . ?
C38 C37 H37 120.0 . . ?
C37 C38 C33 120.8(3) . . ?
C37 C38 H38 119.6 . . ?
C33 C38 H38 119.6 . . ?

_diffrn_measured_fraction_theta_max 0.962
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.962
_refine_diff_density_max         0.579
_refine_diff_density_min         -0.474
_refine_diff_density_rms         0.186
####################################################################### 
# 
# 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_ups558kt
_database_code_depnum_ccdc_archive 'CCDC 1030335'
_audit_update_record             
;
2014-10-21 deposited with the CCDC.
2014-12-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H17 N2, C9 H6 O6, C9 H5 O6'
_chemical_formula_sum            'C31 H28 N2 O12'
_chemical_formula_weight         620.55

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'
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   10.979(2)
_cell_length_b                   11.020(2)
_cell_length_c                   14.010(3)
_cell_angle_alpha                89.54(3)
_cell_angle_beta                 78.13(3)
_cell_angle_gamma                77.87(3)
_cell_volume                     1620.7(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    100
_cell_measurement_theta_min      2.88
_cell_measurement_theta_max      28.45

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648.0
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.970
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      273(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  'CCD area detector'
_diffrn_measurement_method       'phi omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            32695
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_av_sigmaI/netI    0.0362
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.49
_diffrn_reflns_theta_max         27.00
_reflns_number_total             7062
_reflns_number_gt                4309
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker Kappa Apex'
_computing_cell_refinement       'Bruker Kappa Apex'
_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)+(0.1000P)²+0.9257P] 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         7062
_refine_ls_number_parameters     408
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0938
_refine_ls_R_factor_gt           0.0531
_refine_ls_wR_factor_ref         0.1968
_refine_ls_wR_factor_gt          0.1479
_refine_ls_goodness_of_fit_ref   0.966
_refine_ls_restrained_S_all      0.966
_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 0.92574(16) 0.24373(16) 1.05228(12) 0.0486(4) Uani 1 1 d . . .
H1 H 0.9587 0.2927 1.0766 0.073 Uiso 1 1 calc R . .
O2 O 1.08942(17) 0.24935(17) 0.92130(12) 0.0538(5) Uani 1 1 d . . .
O3 O 1.16262(17) -0.03944(19) 0.62656(13) 0.0594(5) Uani 1 1 d . . .
O4 O 0.99937(16) -0.12647(18) 0.60452(12) 0.0537(5) Uani 1 1 d . . .
O5 O 0.63739(17) -0.04682(19) 1.04249(13) 0.0572(5) Uani 1 1 d . . .
H5 H 0.5831 -0.0864 1.0646 0.086 Uiso 1 1 calc R . .
O6 O 0.66603(17) -0.17626(17) 0.90797(13) 0.0567(5) Uani 1 1 d . . .
O7 O 0.12335(17) 0.80943(19) 0.43275(13) 0.0573(5) Uani 1 1 d . . .
H7 H 0.0818 0.8252 0.4886 0.086 Uiso 1 1 calc R . .
O8 O -0.03447(16) 0.70954(18) 0.42043(14) 0.0601(5) Uani 1 1 d . . .
O9 O 0.46166(17) 0.83073(18) 0.13197(13) 0.0558(5) Uani 1 1 d . . .
O10 O 0.48985(19) 0.6985(2) -0.00019(14) 0.0665(6) Uani 1 1 d . . .
H10 H 0.5460 0.7359 -0.0222 0.100 Uiso 1 1 calc R . .
O11 O 0.18460(19) 0.42334(18) -0.00402(12) 0.0572(5) Uani 1 1 d . . .
H11 H 0.1543 0.3704 -0.0261 0.086 Uiso 1 1 calc R . .
O12 O 0.03719(17) 0.40276(18) 0.13484(13) 0.0574(5) Uani 1 1 d . . .
N1 N 0.30424(18) 1.0375(2) 0.46233(15) 0.0490(5) Uani 1 1 d . . .
H1A H 0.2735 0.9890 0.5047 0.059 Uiso 1 1 calc R . .
N2 N 0.25151(19) 1.1600(2) 0.45485(16) 0.0521(6) Uani 1 1 d . . .
H2A H 0.1831 1.2008 0.4921 0.063 Uiso 1 1 calc R . .
C1 C 0.9796(2) -0.0227(2) 0.76060(15) 0.0341(5) Uani 1 1 d . . .
C2 C 1.0188(2) 0.0664(2) 0.81344(16) 0.0352(5) Uani 1 1 d . . .
H2 H 1.0899 0.0972 0.7852 0.042 Uiso 1 1 calc R . .
C3 C 0.95014(19) 0.10931(19) 0.90966(15) 0.0325(5) Uani 1 1 d . . .
C4 C 0.84329(19) 0.0601(2) 0.95542(16) 0.0348(5) Uani 1 1 d . . .
H4A H 0.7992 0.0870 1.0182 0.042 Uiso 1 1 calc R . .
C5 C 0.80522(19) -0.0311(2) 0.90327(16) 0.0349(5) Uani 1 1 d . . .
C6 C 0.8722(2) -0.0714(2) 0.80522(16) 0.0359(5) Uani 1 1 d . . .
H6 H 0.8452 -0.1292 0.7711 0.043 Uiso 1 1 calc R . .
C7 C 1.0546(2) -0.0649(2) 0.65594(16) 0.0385(5) Uani 1 1 d . . .
C8 C 0.9940(2) 0.2072(2) 0.96262(16) 0.0358(5) Uani 1 1 d . . .
C9 C 0.6955(2) -0.0900(2) 0.95324(17) 0.0396(5) Uani 1 1 d . . .
C10 C 0.32541(19) 0.6830(2) 0.14258(16) 0.0353(5) Uani 1 1 d . . .
C11 C 0.2847(2) 0.5909(2) 0.09313(16) 0.0372(5) Uani 1 1 d . . .
H11A H 0.3278 0.5615 0.0306 0.045 Uiso 1 1 calc R . .
C12 C 0.1769(2) 0.5449(2) 0.14140(16) 0.0354(5) Uani 1 1 d . . .
C13 C 0.1097(2) 0.5918(2) 0.23713(16) 0.0356(5) Uani 1 1 d . . .
H13 H 0.0384 0.5624 0.2672 0.043 Uiso 1 1 calc R . .
C14 C 0.15086(19) 0.6828(2) 0.28656(15) 0.0336(5) Uani 1 1 d . . .
C15 C 0.2596(2) 0.7280(2) 0.23944(16) 0.0356(5) Uani 1 1 d . . .
H15 H 0.2881 0.7867 0.2714 0.043 Uiso 1 1 calc R . .
C16 C 0.4337(2) 0.7416(2) 0.08968(17) 0.0394(5) Uani 1 1 d . . .
C17 C 0.1269(2) 0.4501(2) 0.09007(17) 0.0387(5) Uani 1 1 d . . .
C18 C 0.0725(2) 0.7368(2) 0.38805(16) 0.0381(5) Uani 1 1 d . . .
C19 C 0.2850(4) 1.3414(4) 0.3508(3) 0.1073(15) Uani 1 1 d . . .
H19A H 0.1946 1.3620 0.3548 0.161 Uiso 1 1 calc R . .
H19B H 0.3282 1.3510 0.2852 0.161 Uiso 1 1 calc R . .
H19C H 0.3074 1.3956 0.3944 0.161 Uiso 1 1 calc R . .
C20 C 0.3241(3) 1.2073(3) 0.3792(2) 0.0611(8) Uani 1 1 d . . .
C21 C 0.4292(3) 1.1102(3) 0.3383(2) 0.0644(8) Uani 1 1 d . . .
H21 H 0.4953 1.1162 0.2862 0.077 Uiso 1 1 calc R . .
C22 C 0.4146(2) 1.0029(3) 0.39157(17) 0.0453(6) Uani 1 1 d . . .
C23 C 0.4949(2) 0.8736(3) 0.37813(17) 0.0455(6) Uani 1 1 d . . .
C24 C 0.4509(3) 0.7695(3) 0.4210(2) 0.0663(8) Uani 1 1 d . . .
H24 H 0.3724 0.7811 0.4642 0.080 Uiso 1 1 calc R . .
C25 C 0.5258(3) 0.6479(3) 0.3983(3) 0.0812(11) Uani 1 1 d . . .
H25 H 0.4943 0.5809 0.4261 0.097 Uiso 1 1 calc R . .
C26 C 0.6478(3) 0.6253(3) 0.3343(2) 0.0644(8) Uani 1 1 d . . .
C27 C 0.6922(3) 0.7292(3) 0.2948(2) 0.0643(8) Uani 1 1 d . . .
H27 H 0.7724 0.7175 0.2541 0.077 Uiso 1 1 calc R . .
C28 C 0.6188(2) 0.8507(3) 0.3153(2) 0.0597(7) Uani 1 1 d . . .
H28 H 0.6512 0.9172 0.2875 0.072 Uiso 1 1 calc R . .
C29 C 0.7308(4) 0.4926(4) 0.3064(4) 0.1056(10) Uani 1 1 d . . .
H29 H 0.7990 0.5012 0.2510 0.127 Uiso 1 1 calc R . .
C30 C 0.7967(4) 0.4405(4) 0.3915(4) 0.1056(10) Uani 1 1 d . . .
H30A H 0.7337 0.4234 0.4454 0.158 Uiso 1 1 calc R . .
H30B H 0.8387 0.5008 0.4120 0.158 Uiso 1 1 calc R . .
H30C H 0.8582 0.3653 0.3694 0.158 Uiso 1 1 calc R . .
C31 C 0.6582(5) 0.4030(5) 0.2724(6) 0.178(3) Uani 1 1 d . . .
H31A H 0.5925 0.3892 0.3255 0.267 Uiso 1 1 calc R . .
H31B H 0.7159 0.3255 0.2506 0.267 Uiso 1 1 calc R . .
H31C H 0.6205 0.4380 0.2196 0.267 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C8 1.340(3) . ?
O1 H1 0.8200 . ?
O2 C8 1.264(3) . ?
O3 C7 1.261(3) . ?
O4 C7 1.307(3) . ?
O5 C9 1.323(3) . ?
O5 H5 0.8200 . ?
O6 C9 1.278(3) . ?
O7 C18 1.298(3) . ?
O7 H7 0.8200 . ?
O8 C18 1.265(3) . ?
O9 C16 1.273(3) . ?
O10 C16 1.326(3) . ?
O10 H10 0.8200 . ?
O11 C17 1.345(3) . ?
O11 H11 0.8200 . ?
O12 C17 1.261(3) . ?
N1 N2 1.365(3) . ?
N1 C22 1.384(3) . ?
N1 H1A 0.8600 . ?
N2 C20 1.360(3) . ?
N2 H2A 0.8600 . ?
C1 C2 1.420(3) . ?
C1 C6 1.424(3) . ?
C1 C7 1.549(3) . ?
C2 C3 1.432(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.426(3) . ?
C3 C8 1.525(3) . ?
C4 C5 1.426(3) . ?
C4 H4A 0.9300 . ?
C5 C6 1.443(3) . ?
C5 C9 1.529(3) . ?
C6 H6 0.9300 . ?
C10 C11 1.428(3) . ?
C10 C15 1.437(3) . ?
C10 C16 1.527(3) . ?
C11 C12 1.427(3) . ?
C11 H11A 0.9300 . ?
C12 C13 1.433(3) . ?
C12 C17 1.525(3) . ?
C13 C14 1.421(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.424(3) . ?
C14 C18 1.553(3) . ?
C15 H15 0.9300 . ?
C19 C20 1.523(5) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.423(4) . ?
C21 C22 1.414(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.501(4) . ?
C23 C24 1.419(4) . ?
C23 C28 1.433(3) . ?
C24 C25 1.417(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.425(4) . ?
C25 H25 0.9300 . ?
C26 C27 1.403(4) . ?
C26 C29 1.557(5) . ?
C27 C28 1.407(4) . ?
C27 H27 0.9300 . ?
C28 H28 0.9300 . ?
C29 C31 1.527(7) . ?
C29 C30 1.563(7) . ?
C29 H29 0.9800 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 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
C8 O1 H1 109.5 . . ?
C9 O5 H5 109.5 . . ?
C18 O7 H7 109.5 . . ?
C16 O10 H10 109.5 . . ?
C17 O11 H11 109.5 . . ?
N2 N1 C22 109.8(2) . . ?
N2 N1 H1A 125.1 . . ?
C22 N1 H1A 125.1 . . ?
C20 N2 N1 109.3(2) . . ?
C20 N2 H2A 125.3 . . ?
N1 N2 H2A 125.3 . . ?
C2 C1 C6 119.19(19) . . ?
C2 C1 C7 119.37(18) . . ?
C6 C1 C7 121.45(19) . . ?
C1 C2 C3 120.86(18) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 H2 119.6 . . ?
C4 C3 C2 120.38(19) . . ?
C4 C3 C8 120.66(18) . . ?
C2 C3 C8 118.96(17) . . ?
C5 C4 C3 118.87(19) . . ?
C5 C4 H4A 120.6 . . ?
C3 C4 H4A 120.6 . . ?
C4 C5 C6 120.61(18) . . ?
C4 C5 C9 119.54(19) . . ?
C6 C5 C9 119.82(19) . . ?
C1 C6 C5 120.06(19) . . ?
C1 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
O3 C7 O4 124.8(2) . . ?
O3 C7 C1 119.2(2) . . ?
O4 C7 C1 115.95(18) . . ?
O2 C8 O1 124.0(2) . . ?
O2 C8 C3 119.90(19) . . ?
O1 C8 C3 116.10(17) . . ?
O6 C9 O5 124.43(19) . . ?
O6 C9 C5 119.28(19) . . ?
O5 C9 C5 116.29(19) . . ?
C11 C10 C15 120.72(18) . . ?
C11 C10 C16 119.86(19) . . ?
C15 C10 C16 119.27(19) . . ?
C12 C11 C10 118.74(19) . . ?
C12 C11 H11A 120.6 . . ?
C10 C11 H11A 120.6 . . ?
C11 C12 C13 120.42(19) . . ?
C11 C12 C17 120.64(19) . . ?
C13 C12 C17 118.87(18) . . ?
C14 C13 C12 120.77(18) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C13 C14 C15 119.16(19) . . ?
C13 C14 C18 119.65(18) . . ?
C15 C14 C18 121.09(19) . . ?
C14 C15 C10 120.18(19) . . ?
C14 C15 H15 119.9 . . ?
C10 C15 H15 119.9 . . ?
O9 C16 O10 123.97(19) . . ?
O9 C16 C10 119.00(19) . . ?
O10 C16 C10 116.98(19) . . ?
O12 C17 O11 124.2(2) . . ?
O12 C17 C12 120.73(19) . . ?
O11 C17 C12 115.10(18) . . ?
O8 C18 O7 125.0(2) . . ?
O8 C18 C14 119.23(19) . . ?
O7 C18 C14 115.75(18) . . ?
C20 C19 H19A 109.5 . . ?
C20 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C20 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N2 C20 C21 107.4(2) . . ?
N2 C20 C19 120.9(3) . . ?
C21 C20 C19 131.7(3) . . ?
C22 C21 C20 107.3(2) . . ?
C22 C21 H21 126.4 . . ?
C20 C21 H21 126.4 . . ?
N1 C22 C21 106.2(2) . . ?
N1 C22 C23 123.6(2) . . ?
C21 C22 C23 130.1(2) . . ?
C24 C23 C28 117.4(3) . . ?
C24 C23 C22 122.7(2) . . ?
C28 C23 C22 119.8(2) . . ?
C25 C24 C23 120.4(2) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C24 C25 C26 122.0(3) . . ?
C24 C25 H25 119.0 . . ?
C26 C25 H25 119.0 . . ?
C27 C26 C25 117.1(3) . . ?
C27 C26 C29 119.8(3) . . ?
C25 C26 C29 123.1(3) . . ?
C26 C27 C28 121.8(2) . . ?
C26 C27 H27 119.1 . . ?
C28 C27 H27 119.1 . . ?
C27 C28 C23 121.2(3) . . ?
C27 C28 H28 119.4 . . ?
C23 C28 H28 119.4 . . ?
C31 C29 C26 113.4(4) . . ?
C31 C29 C30 112.3(4) . . ?
C26 C29 C30 110.5(4) . . ?
C31 C29 H29 106.7 . . ?
C26 C29 H29 106.7 . . ?
C30 C29 H29 106.7 . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C29 C31 H31A 109.5 . . ?
C29 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C29 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 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
C22 N1 N2 C20 0.9(3) . . . . ?
C6 C1 C2 C3 -1.4(3) . . . . ?
C7 C1 C2 C3 178.8(2) . . . . ?
C1 C2 C3 C4 2.1(3) . . . . ?
C1 C2 C3 C8 -178.6(2) . . . . ?
C2 C3 C4 C5 -0.8(3) . . . . ?
C8 C3 C4 C5 179.9(2) . . . . ?
C3 C4 C5 C6 -1.1(3) . . . . ?
C3 C4 C5 C9 176.7(2) . . . . ?
C2 C1 C6 C5 -0.6(3) . . . . ?
C7 C1 C6 C5 179.3(2) . . . . ?
C4 C5 C6 C1 1.8(3) . . . . ?
C9 C5 C6 C1 -176.0(2) . . . . ?
C2 C1 C7 O3 14.0(3) . . . . ?
C6 C1 C7 O3 -165.8(2) . . . . ?
C2 C1 C7 O4 -166.5(2) . . . . ?
C6 C1 C7 O4 13.6(3) . . . . ?
C4 C3 C8 O2 179.5(2) . . . . ?
C2 C3 C8 O2 0.2(3) . . . . ?
C4 C3 C8 O1 -0.8(3) . . . . ?
C2 C3 C8 O1 179.8(2) . . . . ?
C4 C5 C9 O6 -176.4(2) . . . . ?
C6 C5 C9 O6 1.4(3) . . . . ?
C4 C5 C9 O5 3.3(3) . . . . ?
C6 C5 C9 O5 -178.9(2) . . . . ?
C15 C10 C11 C12 0.4(3) . . . . ?
C16 C10 C11 C12 -175.0(2) . . . . ?
C10 C11 C12 C13 1.0(3) . . . . ?
C10 C11 C12 C17 177.7(2) . . . . ?
C11 C12 C13 C14 -1.5(3) . . . . ?
C17 C12 C13 C14 -178.3(2) . . . . ?
C12 C13 C14 C15 0.5(3) . . . . ?
C12 C13 C14 C18 177.0(2) . . . . ?
C13 C14 C15 C10 0.8(3) . . . . ?
C18 C14 C15 C10 -175.6(2) . . . . ?
C11 C10 C15 C14 -1.3(3) . . . . ?
C16 C10 C15 C14 174.2(2) . . . . ?
C11 C10 C16 O9 174.2(2) . . . . ?
C15 C10 C16 O9 -1.3(3) . . . . ?
C11 C10 C16 O10 -3.3(3) . . . . ?
C15 C10 C16 O10 -178.8(2) . . . . ?
C11 C12 C17 O12 175.0(2) . . . . ?
C13 C12 C17 O12 -8.2(3) . . . . ?
C11 C12 C17 O11 -5.4(3) . . . . ?
C13 C12 C17 O11 171.4(2) . . . . ?
C13 C14 C18 O8 -7.9(3) . . . . ?
C15 C14 C18 O8 168.5(2) . . . . ?
C13 C14 C18 O7 173.1(2) . . . . ?
C15 C14 C18 O7 -10.6(3) . . . . ?
N1 N2 C20 C21 -1.2(3) . . . . ?
N1 N2 C20 C19 177.3(3) . . . . ?
N2 C20 C21 C22 1.1(4) . . . . ?
C19 C20 C21 C22 -177.2(4) . . . . ?
N2 N1 C22 C21 -0.2(3) . . . . ?
N2 N1 C22 C23 -178.8(2) . . . . ?
C20 C21 C22 N1 -0.6(3) . . . . ?
C20 C21 C22 C23 177.9(3) . . . . ?
N1 C22 C23 C24 14.9(4) . . . . ?
C21 C22 C23 C24 -163.4(3) . . . . ?
N1 C22 C23 C28 -168.9(2) . . . . ?
C21 C22 C23 C28 12.9(4) . . . . ?
C28 C23 C24 C25 -2.5(5) . . . . ?
C22 C23 C24 C25 173.9(3) . . . . ?
C23 C24 C25 C26 1.4(6) . . . . ?
C24 C25 C26 C27 0.7(6) . . . . ?
C24 C25 C26 C29 -178.6(4) . . . . ?
C25 C26 C27 C28 -1.5(5) . . . . ?
C29 C26 C27 C28 177.8(3) . . . . ?
C26 C27 C28 C23 0.3(5) . . . . ?
C24 C23 C28 C27 1.7(4) . . . . ?
C22 C23 C28 C27 -174.8(3) . . . . ?
C27 C26 C29 C31 -129.4(5) . . . . ?
C25 C26 C29 C31 49.9(6) . . . . ?
C27 C26 C29 C30 103.5(4) . . . . ?
C25 C26 C29 C30 -77.2(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.629
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.111
####################################################################### 
# 
# 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_ups581kt_0m_2
_database_code_depnum_ccdc_archive 'CCDC 1030336'
_audit_update_record             
;
2014-10-21 deposited with the CCDC.
2014-12-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H13 N2, C15 H12 N2, C9 H5 O6, C H4 O'
_chemical_formula_sum            'C40 H34 N4 O7'
_chemical_formula_weight         682.71

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   7.9394(17)
_cell_length_b                   11.221(2)
_cell_length_c                   19.683(4)
_cell_angle_alpha                93.603(8)
_cell_angle_beta                 92.516(7)
_cell_angle_gamma                95.843(7)
_cell_volume                     1738.7(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    106
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      29.43

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             716.0
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.978
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'

_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  'CCD area detector'
_diffrn_measurement_method       'phi omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9921
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_sigmaI/netI    0.0353
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.83
_diffrn_reflns_theta_max         24.99
_reflns_number_total             6132
_reflns_number_gt                3566
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker Kappa Apex'
_computing_cell_refinement       'Bruker Kappa Apex'
_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)+(0.1000P)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    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.051(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6132
_refine_ls_number_parameters     465
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0747
_refine_ls_R_factor_gt           0.0517
_refine_ls_wR_factor_ref         0.1713
_refine_ls_wR_factor_gt          0.1325
_refine_ls_goodness_of_fit_ref   1.189
_refine_ls_restrained_S_all      1.189
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.1044(3) 0.50192(17) 0.79940(9) 0.0739(6) Uani 1 1 d . . .
O2 O 0.0327(3) 0.34919(15) 0.83182(10) 0.0733(6) Uani 1 1 d . . .
H2A H -0.0258 0.3126 0.8003 0.110 Uiso 1 1 calc R . .
O3 O 0.3721(2) 0.38814(14) 1.04641(8) 0.0541(5) Uani 1 1 d . . .
O4 O 0.4159(2) 0.56549(14) 1.10610(8) 0.0595(5) Uani 1 1 d . . .
O5 O 0.1235(3) 0.90358(15) 1.03306(9) 0.0712(6) Uani 1 1 d . . .
O6 O -0.0482(3) 0.87851(16) 0.93935(10) 0.0721(6) Uani 1 1 d . . .
H6A H -0.0644 0.9477 0.9510 0.108 Uiso 1 1 calc R . .
O7 O 0.8438(3) 0.20542(17) 0.74167(9) 0.0728(6) Uani 1 1 d . . .
H7 H 0.8118 0.2408 0.7091 0.109 Uiso 1 1 calc R . .
N1 N 0.2319(3) 0.54742(19) 0.33170(10) 0.0625(6) Uani 1 1 d . . .
H1 H 0.2092 0.5322 0.2887 0.075 Uiso 1 1 calc R . .
N2 N 0.2582(3) 0.65913(19) 0.36233(10) 0.0619(6) Uani 1 1 d . . .
N3 N 0.5732(3) 0.42786(19) 0.19090(10) 0.0540(6) Uani 1 1 d . . .
H3 H 0.5288 0.4904 0.1786 0.065 Uiso 1 1 calc R . .
N4 N 0.5560(3) 0.31982(18) 0.15715(10) 0.0536(6) Uani 1 1 d . . .
H4A H 0.4973 0.3021 0.1195 0.064 Uiso 1 1 calc R . .
C1 C 0.2465(3) 0.55239(19) 1.00345(10) 0.0401(6) Uani 1 1 d . . .
C2 C 0.2095(3) 0.66988(19) 1.01422(11) 0.0433(6) Uani 1 1 d . . .
H2 H 0.2555 0.7163 1.0527 0.052 Uiso 1 1 calc R . .
C3 C 0.1040(3) 0.71841(19) 0.96770(11) 0.0424(6) Uani 1 1 d . . .
C4 C 0.0382(3) 0.6498(2) 0.90994(11) 0.0440(6) Uani 1 1 d . . .
H4 H -0.0310 0.6827 0.8784 0.053 Uiso 1 1 calc R . .
C5 C 0.0749(3) 0.53185(19) 0.89885(10) 0.0402(6) Uani 1 1 d . . .
C6 C 0.1789(3) 0.4837(2) 0.94553(11) 0.0425(6) Uani 1 1 d . . .
H6 H 0.2039 0.4049 0.9382 0.051 Uiso 1 1 calc R . .
C7 C 0.3523(3) 0.4963(2) 1.05478(11) 0.0456(6) Uani 1 1 d . . .
C8 C 0.0591(3) 0.8418(2) 0.98163(12) 0.0488(6) Uani 1 1 d . . .
C9 C -0.0052(3) 0.4584(2) 0.83845(12) 0.0490(6) Uani 1 1 d . . .
C10 C 0.2673(4) 0.8591(3) 0.46519(15) 0.0751(9) Uani 1 1 d . . .
H10 H 0.2166 0.8692 0.4227 0.090 Uiso 1 1 calc R . .
C11 C 0.2906(5) 0.9539(3) 0.51358(17) 0.0920(11) Uani 1 1 d . . .
H11 H 0.2565 1.0279 0.5034 0.110 Uiso 1 1 calc R . .
C12 C 0.3635(4) 0.9405(3) 0.57691(16) 0.0844(10) Uani 1 1 d . . .
H12 H 0.3773 1.0047 0.6096 0.101 Uiso 1 1 calc R . .
C13 C 0.4154(4) 0.8327(3) 0.59134(14) 0.0768(9) Uani 1 1 d . . .
H13 H 0.4658 0.8236 0.6340 0.092 Uiso 1 1 calc R . .
C14 C 0.3938(4) 0.7367(3) 0.54320(13) 0.0681(8) Uani 1 1 d . . .
H14 H 0.4297 0.6633 0.5537 0.082 Uiso 1 1 calc R . .
C15 C 0.3191(3) 0.7486(2) 0.47935(13) 0.0561(7) Uani 1 1 d . . .
C16 C 0.2913(3) 0.6448(2) 0.42869(12) 0.0561(7) Uani 1 1 d . . .
C17 C 0.2864(3) 0.5229(2) 0.43899(13) 0.0610(7) Uani 1 1 d . . .
H17 H 0.3067 0.4886 0.4800 0.073 Uiso 1 1 calc R . .
C18 C 0.2454(3) 0.4631(2) 0.37611(13) 0.0553(7) Uani 1 1 d . . .
C19 C 0.2098(3) 0.3344(2) 0.35495(13) 0.0556(7) Uani 1 1 d . . .
C20 C 0.1316(4) 0.2562(3) 0.39906(14) 0.0715(8) Uani 1 1 d . . .
H20 H 0.1050 0.2853 0.4421 0.086 Uiso 1 1 calc R . .
C21 C 0.0934(4) 0.1363(3) 0.37945(16) 0.0793(9) Uani 1 1 d . . .
H21 H 0.0413 0.0847 0.4093 0.095 Uiso 1 1 calc R . .
C22 C 0.1323(4) 0.0925(3) 0.31570(17) 0.0789(9) Uani 1 1 d . . .
H22 H 0.1068 0.0114 0.3024 0.095 Uiso 1 1 calc R . .
C23 C 0.2083(4) 0.1685(3) 0.27204(16) 0.0764(9) Uani 1 1 d . . .
H23 H 0.2341 0.1389 0.2290 0.092 Uiso 1 1 calc R . .
C24 C 0.2469(3) 0.2883(3) 0.29111(13) 0.0638(8) Uani 1 1 d . . .
H24 H 0.2986 0.3390 0.2608 0.077 Uiso 1 1 calc R . .
C25 C 0.6630(5) 0.6369(3) 0.28331(18) 0.0987(11) Uani 1 1 d . . .
H25 H 0.5991 0.6459 0.2436 0.118 Uiso 1 1 calc R . .
C26 C 0.7051(6) 0.7346(4) 0.3290(2) 0.1254(15) Uani 1 1 d . . .
H26 H 0.6700 0.8088 0.3198 0.150 Uiso 1 1 calc R . .
C27 C 0.7983(5) 0.7228(4) 0.38758(19) 0.1050(12) Uani 1 1 d . . .
H27 H 0.8250 0.7886 0.4187 0.126 Uiso 1 1 calc R . .
C28 C 0.8519(4) 0.6153(4) 0.40054(15) 0.0905(11) Uani 1 1 d . . .
H28 H 0.9168 0.6077 0.4402 0.109 Uiso 1 1 calc R . .
C29 C 0.8103(4) 0.5171(3) 0.35489(14) 0.0741(8) Uani 1 1 d . . .
H29 H 0.8477 0.4437 0.3641 0.089 Uiso 1 1 calc R . .
C30 C 0.7134(3) 0.5266(3) 0.29539(12) 0.0599(7) Uani 1 1 d . . .
C31 C 0.6712(3) 0.4217(2) 0.24688(12) 0.0526(7) Uani 1 1 d . . .
C32 C 0.7176(3) 0.3064(2) 0.24785(12) 0.0566(7) Uani 1 1 d . . .
H32 H 0.7861 0.2773 0.2812 0.068 Uiso 1 1 calc R . .
C33 C 0.6433(3) 0.2427(2) 0.19024(12) 0.0516(7) Uani 1 1 d . . .
C34 C 0.6488(3) 0.1179(2) 0.16427(13) 0.0566(7) Uani 1 1 d . . .
C35 C 0.7616(4) 0.0483(3) 0.19338(19) 0.0915(11) Uani 1 1 d . . .
H35 H 0.8330 0.0810 0.2300 0.110 Uiso 1 1 calc R . .
C36 C 0.7712(5) -0.0684(3) 0.1695(2) 0.1123(14) Uani 1 1 d . . .
H36 H 0.8478 -0.1140 0.1902 0.135 Uiso 1 1 calc R . .
C37 C 0.6677(5) -0.1178(3) 0.1150(2) 0.1017(12) Uani 1 1 d . . .
H37 H 0.6749 -0.1964 0.0983 0.122 Uiso 1 1 calc R . .
C38 C 0.5554(5) -0.0513(3) 0.08584(18) 0.0899(10) Uani 1 1 d . . .
H38 H 0.4848 -0.0844 0.0490 0.108 Uiso 1 1 calc R . .
C39 C 0.5450(4) 0.0652(3) 0.11028(15) 0.0726(8) Uani 1 1 d . . .
H39 H 0.4661 0.1094 0.0899 0.087 Uiso 1 1 calc R . .
C40 C 0.7020(4) 0.1636(3) 0.77819(17) 0.0949(11) Uani 1 1 d . . .
H40A H 0.7385 0.1172 0.8143 0.142 Uiso 1 1 calc R . .
H40B H 0.6215 0.1145 0.7479 0.142 Uiso 1 1 calc R . .
H40C H 0.6499 0.2310 0.7971 0.142 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C9 1.234(3) . ?
O2 C9 1.292(3) . ?
O2 H2A 0.8200 . ?
O3 C7 1.241(3) . ?
O4 C7 1.286(3) . ?
O5 C8 1.250(3) . ?
O6 C8 1.280(3) . ?
O6 H6A 0.8200 . ?
O7 C40 1.418(3) . ?
O7 H7 0.8200 . ?
N1 C18 1.337(3) . ?
N1 N2 1.349(3) . ?
N1 H1 0.8600 . ?
N2 C16 1.344(3) . ?
N3 N4 1.337(3) . ?
N3 C31 1.330(3) . ?
N3 H3 0.8600 . ?
N4 C33 1.344(3) . ?
N4 H4A 0.8600 . ?
C1 C2 1.385(3) . ?
C1 C6 1.390(3) . ?
C1 C7 1.495(3) . ?
C2 C3 1.387(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.384(3) . ?
C3 C8 1.477(3) . ?
C4 C5 1.389(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.380(3) . ?
C5 C9 1.483(3) . ?
C6 H6 0.9300 . ?
C10 C11 1.374(4) . ?
C10 C15 1.386(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.375(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.359(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.382(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.386(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.477(3) . ?
C16 C17 1.393(4) . ?
C17 C18 1.380(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.473(3) . ?
C19 C24 1.384(4) . ?
C19 C20 1.393(4) . ?
C20 C21 1.376(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.378(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.365(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.372(4) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 C30 1.370(4) . ?
C25 C26 1.377(5) . ?
C25 H25 0.9300 . ?
C26 C27 1.364(5) . ?
C26 H26 0.9300 . ?
C27 C28 1.355(5) . ?
C27 H27 0.9300 . ?
C28 C29 1.381(4) . ?
C28 H28 0.9300 . ?
C29 C30 1.389(4) . ?
C29 H29 0.9300 . ?
C30 C31 1.470(4) . ?
C31 C32 1.381(4) . ?
C32 C33 1.378(3) . ?
C32 H32 0.9300 . ?
C33 C34 1.466(4) . ?
C34 C39 1.380(4) . ?
C34 C35 1.377(4) . ?
C35 C36 1.374(5) . ?
C35 H35 0.9300 . ?
C36 C37 1.375(5) . ?
C36 H36 0.9300 . ?
C37 C38 1.351(5) . ?
C37 H37 0.9300 . ?
C38 C39 1.375(4) . ?
C38 H38 0.9300 . ?
C39 H39 0.9300 . ?
C40 H40A 0.9600 . ?
C40 H40B 0.9600 . ?
C40 H40C 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
C9 O2 H2A 109.5 . . ?
C8 O6 H6A 109.5 . . ?
C40 O7 H7 109.5 . . ?
C18 N1 N2 112.0(2) . . ?
C18 N1 H1 124.0 . . ?
N2 N1 H1 124.0 . . ?
C16 N2 N1 105.9(2) . . ?
N4 N3 C31 108.0(2) . . ?
N4 N3 H3 126.0 . . ?
C31 N3 H3 126.0 . . ?
N3 N4 C33 110.62(19) . . ?
N3 N4 H4A 124.7 . . ?
C33 N4 H4A 124.7 . . ?
C2 C1 C6 119.8(2) . . ?
C2 C1 C7 120.9(2) . . ?
C6 C1 C7 119.3(2) . . ?
C1 C2 C3 120.1(2) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C4 C3 C2 119.8(2) . . ?
C4 C3 C8 120.8(2) . . ?
C2 C3 C8 119.4(2) . . ?
C3 C4 C5 120.4(2) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 119.6(2) . . ?
C6 C5 C9 121.3(2) . . ?
C4 C5 C9 119.1(2) . . ?
C5 C6 C1 120.4(2) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
O3 C7 O4 124.2(2) . . ?
O3 C7 C1 119.5(2) . . ?
O4 C7 C1 116.3(2) . . ?
O5 C8 O6 123.7(2) . . ?
O5 C8 C3 119.8(2) . . ?
O6 C8 C3 116.5(2) . . ?
O1 C9 O2 124.3(2) . . ?
O1 C9 C5 119.9(2) . . ?
O2 C9 C5 115.8(2) . . ?
C11 C10 C15 120.3(3) . . ?
C11 C10 H10 119.8 . . ?
C15 C10 H10 119.8 . . ?
C10 C11 C12 120.8(3) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C13 C12 C11 119.5(3) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C12 C13 C14 120.6(3) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C13 C14 C15 120.6(3) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C14 C15 C10 118.3(2) . . ?
C14 C15 C16 120.5(2) . . ?
C10 C15 C16 121.2(2) . . ?
N2 C16 C17 109.5(2) . . ?
N2 C16 C15 121.5(2) . . ?
C17 C16 C15 129.0(2) . . ?
C18 C17 C16 106.2(2) . . ?
C18 C17 H17 126.9 . . ?
C16 C17 H17 126.9 . . ?
N1 C18 C17 106.5(2) . . ?
N1 C18 C19 121.5(2) . . ?
C17 C18 C19 131.9(2) . . ?
C24 C19 C20 118.2(2) . . ?
C24 C19 C18 122.0(2) . . ?
C20 C19 C18 119.8(2) . . ?
C21 C20 C19 120.6(3) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C20 C21 C22 120.1(3) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C23 C22 C21 119.8(3) . . ?
C23 C22 H22 120.1 . . ?
C21 C22 H22 120.1 . . ?
C22 C23 C24 120.6(3) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 H23 119.7 . . ?
C23 C24 C19 120.8(3) . . ?
C23 C24 H24 119.6 . . ?
C19 C24 H24 119.6 . . ?
C30 C25 C26 121.2(3) . . ?
C30 C25 H25 119.4 . . ?
C26 C25 H25 119.4 . . ?
C27 C26 C25 120.1(4) . . ?
C27 C26 H26 119.9 . . ?
C25 C26 H26 119.9 . . ?
C28 C27 C26 120.1(3) . . ?
C28 C27 H27 120.0 . . ?
C26 C27 H27 120.0 . . ?
C27 C28 C29 120.1(3) . . ?
C27 C28 H28 120.0 . . ?
C29 C28 H28 120.0 . . ?
C28 C29 C30 120.9(3) . . ?
C28 C29 H29 119.6 . . ?
C30 C29 H29 119.6 . . ?
C25 C30 C29 117.7(3) . . ?
C25 C30 C31 121.9(3) . . ?
C29 C30 C31 120.4(3) . . ?
N3 C31 C32 108.2(2) . . ?
N3 C31 C30 121.3(2) . . ?
C32 C31 C30 130.6(2) . . ?
C33 C32 C31 107.2(2) . . ?
C33 C32 H32 126.4 . . ?
C31 C32 H32 126.4 . . ?
N4 C33 C32 106.0(2) . . ?
N4 C33 C34 122.4(2) . . ?
C32 C33 C34 131.6(2) . . ?
C39 C34 C35 117.1(3) . . ?
C39 C34 C33 122.7(3) . . ?
C35 C34 C33 120.2(3) . . ?
C36 C35 C34 121.5(3) . . ?
C36 C35 H35 119.2 . . ?
C34 C35 H35 119.2 . . ?
C37 C36 C35 120.0(4) . . ?
C37 C36 H36 120.0 . . ?
C35 C36 H36 120.0 . . ?
C38 C37 C36 119.5(3) . . ?
C38 C37 H37 120.3 . . ?
C36 C37 H37 120.3 . . ?
C37 C38 C39 120.4(3) . . ?
C37 C38 H38 119.8 . . ?
C39 C38 H38 119.8 . . ?
C38 C39 C34 121.5(3) . . ?
C38 C39 H39 119.2 . . ?
C34 C39 H39 119.2 . . ?
O7 C40 H40A 109.5 . . ?
O7 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
O7 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 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
C18 N1 N2 C16 0.6(3) . . . . ?
C31 N3 N4 C33 -0.5(3) . . . . ?
C6 C1 C2 C3 0.6(3) . . . . ?
C7 C1 C2 C3 -176.7(2) . . . . ?
C1 C2 C3 C4 -1.1(3) . . . . ?
C1 C2 C3 C8 177.0(2) . . . . ?
C2 C3 C4 C5 1.1(3) . . . . ?
C8 C3 C4 C5 -177.0(2) . . . . ?
C3 C4 C5 C6 -0.6(3) . . . . ?
C3 C4 C5 C9 176.6(2) . . . . ?
C4 C5 C6 C1 0.2(3) . . . . ?
C9 C5 C6 C1 -177.1(2) . . . . ?
C2 C1 C6 C5 -0.2(3) . . . . ?
C7 C1 C6 C5 177.20(19) . . . . ?
C2 C1 C7 O3 174.2(2) . . . . ?
C6 C1 C7 O3 -3.1(3) . . . . ?
C2 C1 C7 O4 -4.9(3) . . . . ?
C6 C1 C7 O4 177.77(19) . . . . ?
C4 C3 C8 O5 -178.0(2) . . . . ?
C2 C3 C8 O5 3.9(4) . . . . ?
C4 C3 C8 O6 2.9(4) . . . . ?
C2 C3 C8 O6 -175.2(2) . . . . ?
C6 C5 C9 O1 176.3(2) . . . . ?
C4 C5 C9 O1 -0.9(3) . . . . ?
C6 C5 C9 O2 -1.8(3) . . . . ?
C4 C5 C9 O2 -179.1(2) . . . . ?
C15 C10 C11 C12 -0.7(5) . . . . ?
C10 C11 C12 C13 1.0(6) . . . . ?
C11 C12 C13 C14 -0.6(5) . . . . ?
C12 C13 C14 C15 0.1(5) . . . . ?
C13 C14 C15 C10 0.1(4) . . . . ?
C13 C14 C15 C16 -178.1(3) . . . . ?
C11 C10 C15 C14 0.2(5) . . . . ?
C11 C10 C15 C16 178.4(3) . . . . ?
N1 N2 C16 C17 0.4(3) . . . . ?
N1 N2 C16 C15 -177.1(2) . . . . ?
C14 C15 C16 N2 -163.8(3) . . . . ?
C10 C15 C16 N2 18.1(4) . . . . ?
C14 C15 C16 C17 19.3(4) . . . . ?
C10 C15 C16 C17 -158.8(3) . . . . ?
N2 C16 C17 C18 -1.2(3) . . . . ?
C15 C16 C17 C18 176.0(3) . . . . ?
N2 N1 C18 C17 -1.4(3) . . . . ?
N2 N1 C18 C19 175.6(2) . . . . ?
C16 C17 C18 N1 1.5(3) . . . . ?
C16 C17 C18 C19 -175.0(3) . . . . ?
N1 C18 C19 C24 34.4(4) . . . . ?
C17 C18 C19 C24 -149.6(3) . . . . ?
N1 C18 C19 C20 -143.5(3) . . . . ?
C17 C18 C19 C20 32.5(4) . . . . ?
C24 C19 C20 C21 0.3(4) . . . . ?
C18 C19 C20 C21 178.3(3) . . . . ?
C19 C20 C21 C22 -0.1(5) . . . . ?
C20 C21 C22 C23 -0.2(5) . . . . ?
C21 C22 C23 C24 0.2(5) . . . . ?
C22 C23 C24 C19 0.0(4) . . . . ?
C20 C19 C24 C23 -0.3(4) . . . . ?
C18 C19 C24 C23 -178.3(3) . . . . ?
C30 C25 C26 C27 -0.2(7) . . . . ?
C25 C26 C27 C28 1.1(7) . . . . ?
C26 C27 C28 C29 -0.9(6) . . . . ?
C27 C28 C29 C30 -0.1(5) . . . . ?
C26 C25 C30 C29 -0.8(5) . . . . ?
C26 C25 C30 C31 -179.3(3) . . . . ?
C28 C29 C30 C25 0.9(4) . . . . ?
C28 C29 C30 C31 179.5(2) . . . . ?
N4 N3 C31 C32 0.4(3) . . . . ?
N4 N3 C31 C30 -179.6(2) . . . . ?
C25 C30 C31 N3 -4.1(4) . . . . ?
C29 C30 C31 N3 177.4(2) . . . . ?
C25 C30 C31 C32 175.9(3) . . . . ?
C29 C30 C31 C32 -2.6(4) . . . . ?
N3 C31 C32 C33 -0.2(3) . . . . ?
C30 C31 C32 C33 179.8(2) . . . . ?
N3 N4 C33 C32 0.4(3) . . . . ?
N3 N4 C33 C34 -179.2(2) . . . . ?
C31 C32 C33 N4 -0.2(3) . . . . ?
C31 C32 C33 C34 179.4(2) . . . . ?
N4 C33 C34 C39 -10.4(4) . . . . ?
C32 C33 C34 C39 170.1(3) . . . . ?
N4 C33 C34 C35 169.0(3) . . . . ?
C32 C33 C34 C35 -10.5(4) . . . . ?
C39 C34 C35 C36 0.3(5) . . . . ?
C33 C34 C35 C36 -179.1(3) . . . . ?
C34 C35 C36 C37 0.6(6) . . . . ?
C35 C36 C37 C38 -0.9(6) . . . . ?
C36 C37 C38 C39 0.2(6) . . . . ?
C37 C38 C39 C34 0.7(5) . . . . ?
C35 C34 C39 C38 -1.0(5) . . . . ?
C33 C34 C39 C38 178.4(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.774
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.774
_refine_diff_density_max         0.460
_refine_diff_density_min         -0.442
_refine_diff_density_rms         0.148
####################################################################### 
# 
# 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_ups777kt_0m
_database_code_depnum_ccdc_archive 'CCDC 1030337'
_audit_update_record             
;
2014-10-21 deposited with the CCDC.
2014-12-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H16 N4, 2(C9 H5 O6), C H4 O'
_chemical_formula_sum            'C29 H30 N4 O13'
_chemical_formula_weight         642.57

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

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

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

_cell_length_a                   15.056(2)
_cell_length_b                   13.1093(18)
_cell_length_c                   15.2651(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.105(5)
_cell_angle_gamma                90.00
_cell_volume                     2908.9(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    100
_cell_measurement_theta_min      2.89
_cell_measurement_theta_max      30.31

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1344.0
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.971
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'

_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  'CCD area detector'
_diffrn_measurement_method       'phi omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            42927
_diffrn_reflns_av_R_equivalents  0.0622
_diffrn_reflns_av_sigmaI/netI    0.0332
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.11
_diffrn_reflns_theta_max         25.00
_reflns_number_total             5105
_reflns_number_gt                4491
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker Kappa Apex'
_computing_cell_refinement       'Bruker Kappa Apex'
_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)+(0.0654P)²+10.7229P] 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       0.0016(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5105
_refine_ls_number_parameters     434
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0847
_refine_ls_R_factor_gt           0.0776
_refine_ls_wR_factor_ref         0.2095
_refine_ls_wR_factor_gt          0.2056
_refine_ls_goodness_of_fit_ref   1.175
_refine_ls_restrained_S_all      1.175
_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 1.04337(18) 0.6207(2) 0.08732(18) 0.0256(7) Uani 1 1 d . . .
H1 H 1.0714 0.6207 0.0479 0.038 Uiso 1 1 calc R . .
O2 O 0.92153(18) 0.6113(2) -0.03363(18) 0.0239(6) Uani 1 1 d . . .
O3 O 1.01101(18) 0.6131(2) 0.38816(17) 0.0228(6) Uani 1 1 d . . .
O4 O 0.87376(18) 0.6079(2) 0.41903(17) 0.0207(6) Uani 1 1 d . . .
O5 O 0.61922(18) 0.6099(2) 0.01069(18) 0.0234(6) Uani 1 1 d . . .
H5 H 0.5644 0.6240 -0.0073 0.035 Uiso 1 1 calc R . .
O6 O 0.58974(18) 0.6058(2) 0.14684(18) 0.0226(6) Uani 1 1 d . . .
O7 O 0.98167(17) 0.3694(2) 0.15125(18) 0.0220(6) Uani 1 1 d . . .
H7 H 1.0111 0.3692 0.1130 0.033 Uiso 1 1 calc R . .
O8 O 0.8633(2) 0.3509(3) 0.02884(18) 0.0316(7) Uani 1 1 d . . .
O9 O 0.92685(18) 0.3606(2) 0.44936(17) 0.0233(6) Uani 1 1 d . . .
H9 H 0.9412 0.3715 0.5041 0.035 Uiso 1 1 calc R . .
O10 O 0.78481(18) 0.3520(2) 0.46859(17) 0.0208(6) Uani 1 1 d . . .
O11 O 0.52111(17) 0.3504(2) 0.19013(17) 0.0213(6) Uani 1 1 d . . .
O12 O 0.54983(17) 0.3626(2) 0.05442(17) 0.0191(6) Uani 1 1 d . . .
O13 O 0.9457(3) 0.1211(5) 0.1798(3) 0.0790(16) Uani 1 1 d . . .
H13 H 0.9364 0.1006 0.2273 0.118 Uiso 1 1 calc R . .
N1 N 0.7908(2) 0.2726(2) 0.6275(2) 0.0183(7) Uani 1 1 d . . .
H1B H 0.799(3) 0.290(3) 0.581(3) 0.020(12) Uiso 1 1 d . . .
N2 N 0.8583(2) 0.2225(2) 0.6876(2) 0.0178(7) Uani 1 1 d . . .
H2B H 0.9103 0.2050 0.6787 0.021 Uiso 1 1 calc R . .
N3 N 0.6123(2) 0.2849(3) 0.9161(2) 0.0235(8) Uani 1 1 d . . .
H3A H 0.587(3) 0.318(4) 0.957(3) 0.034(13) Uiso 1 1 d . . .
N4 N 0.6170(2) 0.1828(3) 0.9161(2) 0.0242(8) Uani 1 1 d . . .
H4A H 0.5943 0.1429 0.9493 0.029 Uiso 1 1 calc R . .
C1 C 0.8965(3) 0.6115(3) 0.1129(2) 0.0161(8) Uani 1 1 d . . .
C2 C 0.9357(3) 0.6111(3) 0.2061(2) 0.0166(8) Uani 1 1 d . . .
H2 H 0.9993 0.6135 0.2288 0.020 Uiso 1 1 calc R . .
C3 C 0.8796(3) 0.6073(3) 0.2649(2) 0.0147(7) Uani 1 1 d . . .
C4 C 0.7846(2) 0.6054(3) 0.2303(2) 0.0145(7) Uani 1 1 d . . .
H4 H 0.7469 0.6037 0.2699 0.017 Uiso 1 1 calc R . .
C5 C 0.7451(3) 0.6061(3) 0.1371(2) 0.0164(8) Uani 1 1 d . . .
C6 C 0.8017(3) 0.6086(3) 0.0784(2) 0.0163(8) Uani 1 1 d . . .
H6 H 0.7761 0.6084 0.0160 0.020 Uiso 1 1 calc R . .
C7 C 0.9556(3) 0.6144(3) 0.0495(2) 0.0159(8) Uani 1 1 d . . .
C8 C 0.9230(3) 0.6090(3) 0.3655(2) 0.0165(8) Uani 1 1 d . . .
C9 C 0.6431(3) 0.6072(3) 0.0993(2) 0.0168(8) Uani 1 1 d . . .
C10 C 0.8320(2) 0.3541(3) 0.1717(2) 0.0156(8) Uani 1 1 d . . .
C11 C 0.8655(3) 0.3545(3) 0.2654(2) 0.0156(8) Uani 1 1 d . . .
H11 H 0.9286 0.3539 0.2919 0.019 Uiso 1 1 calc R . .
C12 C 0.8040(3) 0.3558(3) 0.3193(2) 0.0150(7) Uani 1 1 d . . .
C13 C 0.7095(2) 0.3557(3) 0.2787(2) 0.0146(7) Uani 1 1 d . . .
H13A H 0.6684 0.3552 0.3148 0.018 Uiso 1 1 calc R . .
C14 C 0.6761(2) 0.3562(3) 0.1847(2) 0.0143(7) Uani 1 1 d . . .
C15 C 0.7384(3) 0.3555(3) 0.1321(2) 0.0151(8) Uani 1 1 d . . .
H15 H 0.7169 0.3560 0.0692 0.018 Uiso 1 1 calc R . .
C16 C 0.8950(3) 0.3572(3) 0.1117(2) 0.0167(8) Uani 1 1 d . . .
C17 C 0.8401(3) 0.3565(3) 0.4208(2) 0.0170(8) Uani 1 1 d . . .
C18 C 0.5748(2) 0.3565(3) 0.1408(2) 0.0152(8) Uani 1 1 d . . .
C19 C 0.6348(3) 0.3398(3) 0.6115(3) 0.0215(8) Uani 1 1 d . . .
H19A H 0.6407 0.4118 0.6232 0.032 Uiso 1 1 calc R . .
H19B H 0.5830 0.3140 0.6302 0.032 Uiso 1 1 calc R . .
H19C H 0.6258 0.3277 0.5477 0.032 Uiso 1 1 calc R . .
C20 C 0.7200(2) 0.2870(3) 0.6630(2) 0.0167(8) Uani 1 1 d . . .
C21 C 0.7430(3) 0.2438(3) 0.7500(2) 0.0160(7) Uani 1 1 d . . .
C22 C 0.8315(2) 0.2044(3) 0.7634(2) 0.0159(8) Uani 1 1 d . . .
C23 C 0.8934(3) 0.1510(3) 0.8418(3) 0.0236(9) Uani 1 1 d . . .
H23A H 0.8886 0.0786 0.8319 0.035 Uiso 1 1 calc R . .
H23B H 0.8758 0.1675 0.8962 0.035 Uiso 1 1 calc R . .
H23C H 0.9557 0.1722 0.8479 0.035 Uiso 1 1 calc R . .
C26 C 0.6873(2) 0.2403(3) 0.8162(2) 0.0169(8) Uani 1 1 d . . .
C25 C 0.6542(3) 0.3234(3) 0.8564(3) 0.0213(8) Uani 1 1 d . . .
C24 C 0.6601(3) 0.4352(3) 0.8423(3) 0.0327(10) Uani 1 1 d . . .
H24A H 0.6123 0.4555 0.7902 0.049 Uiso 1 1 calc R . .
H24B H 0.7190 0.4514 0.8326 0.049 Uiso 1 1 calc R . .
H24C H 0.6528 0.4708 0.8949 0.049 Uiso 1 1 calc R . .
C28 C 0.6759(3) 0.0431(3) 0.8409(3) 0.0334(10) Uani 1 1 d . . .
H28A H 0.7229 0.0163 0.8907 0.050 Uiso 1 1 calc R . .
H28B H 0.6941 0.0349 0.7856 0.050 Uiso 1 1 calc R . .
H28C H 0.6194 0.0071 0.8364 0.050 Uiso 1 1 calc R . .
C27 C 0.6623(3) 0.1532(3) 0.8565(3) 0.0212(8) Uani 1 1 d . . .
C29 C 0.8869(5) 0.0721(5) 0.1075(4) 0.0631(18) Uani 1 1 d . . .
H29A H 0.8309 0.1105 0.0879 0.095 Uiso 1 1 calc R . .
H29B H 0.8733 0.0051 0.1259 0.095 Uiso 1 1 calc R . .
H29C H 0.9156 0.0666 0.0584 0.095 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.299(5) . ?
O1 H1 0.8200 . ?
O2 C7 1.240(4) . ?
O3 C8 1.281(5) . ?
O4 C8 1.238(5) . ?
O5 C9 1.307(4) . ?
O5 H5 0.8200 . ?
O6 C9 1.215(5) . ?
O7 C16 1.298(5) . ?
O7 H7 0.8200 . ?
O8 C16 1.232(5) . ?
O9 C17 1.266(5) . ?
O9 H9 0.8200 . ?
O10 C17 1.243(5) . ?
O11 C18 1.242(4) . ?
O12 C18 1.276(4) . ?
O13 C29 1.380(7) . ?
O13 H13 0.8200 . ?
N1 C20 1.330(5) . ?
N1 N2 1.349(5) . ?
N1 H1B 0.78(5) . ?
N2 C22 1.343(5) . ?
N2 H2B 0.8600 . ?
N3 C25 1.334(5) . ?
N3 N4 1.339(5) . ?
N3 H3A 0.92(5) . ?
N4 C27 1.329(5) . ?
N4 H4A 0.8600 . ?
C1 C6 1.388(5) . ?
C1 C2 1.390(5) . ?
C1 C7 1.476(5) . ?
C2 C3 1.386(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.390(5) . ?
C3 C8 1.503(5) . ?
C4 C5 1.391(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.390(5) . ?
C5 C9 1.493(5) . ?
C6 H6 0.9300 . ?
C10 C15 1.381(5) . ?
C10 C11 1.387(5) . ?
C10 C16 1.480(5) . ?
C11 C12 1.390(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.396(5) . ?
C12 C17 1.501(5) . ?
C13 C14 1.390(5) . ?
C13 H13A 0.9300 . ?
C14 C15 1.385(5) . ?
C14 C18 1.498(5) . ?
C15 H15 0.9300 . ?
C19 C20 1.490(5) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.401(5) . ?
C21 C22 1.393(5) . ?
C21 C26 1.472(5) . ?
C22 C23 1.487(5) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C26 C27 1.395(5) . ?
C26 C25 1.404(6) . ?
C25 C24 1.487(6) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C28 C27 1.485(6) . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 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
C7 O1 H1 109.5 . . ?
C9 O5 H5 109.5 . . ?
C16 O7 H7 109.5 . . ?
C17 O9 H9 109.5 . . ?
C29 O13 H13 109.5 . . ?
C20 N1 N2 109.5(3) . . ?
C20 N1 H1B 131(3) . . ?
N2 N1 H1B 120(3) . . ?
C22 N2 N1 109.3(3) . . ?
C22 N2 H2B 125.4 . . ?
N1 N2 H2B 125.4 . . ?
C25 N3 N4 110.1(3) . . ?
C25 N3 H3A 130(3) . . ?
N4 N3 H3A 120(3) . . ?
C27 N4 N3 109.2(3) . . ?
C27 N4 H4A 125.4 . . ?
N3 N4 H4A 125.4 . . ?
C6 C1 C2 120.6(3) . . ?
C6 C1 C7 119.2(3) . . ?
C2 C1 C7 120.2(3) . . ?
C3 C2 C1 119.7(3) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C2 C3 C4 119.7(3) . . ?
C2 C3 C8 119.0(3) . . ?
C4 C3 C8 121.2(3) . . ?
C3 C4 C5 120.8(3) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 119.3(3) . . ?
C6 C5 C9 119.5(3) . . ?
C4 C5 C9 121.2(3) . . ?
C1 C6 C5 119.9(3) . . ?
C1 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
O2 C7 O1 123.9(3) . . ?
O2 C7 C1 120.8(3) . . ?
O1 C7 C1 115.3(3) . . ?
O4 C8 O3 125.2(3) . . ?
O4 C8 C3 119.9(3) . . ?
O3 C8 C3 114.9(3) . . ?
O6 C9 O5 124.9(3) . . ?
O6 C9 C5 122.9(3) . . ?
O5 C9 C5 112.2(3) . . ?
C15 C10 C11 120.5(3) . . ?
C15 C10 C16 118.2(3) . . ?
C11 C10 C16 121.2(3) . . ?
C10 C11 C12 119.4(3) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
C11 C12 C13 119.7(3) . . ?
C11 C12 C17 119.6(3) . . ?
C13 C12 C17 120.7(3) . . ?
C14 C13 C12 120.7(3) . . ?
C14 C13 H13A 119.6 . . ?
C12 C13 H13A 119.6 . . ?
C15 C14 C13 118.8(3) . . ?
C15 C14 C18 120.3(3) . . ?
C13 C14 C18 120.9(3) . . ?
C10 C15 C14 120.9(3) . . ?
C10 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
O8 C16 O7 124.0(3) . . ?
O8 C16 C10 119.6(3) . . ?
O7 C16 C10 116.4(3) . . ?
O10 C17 O9 126.0(3) . . ?
O10 C17 C12 119.2(3) . . ?
O9 C17 C12 114.8(3) . . ?
O11 C18 O12 124.6(3) . . ?
O11 C18 C14 118.4(3) . . ?
O12 C18 C14 117.0(3) . . ?
C20 C19 H19A 109.5 . . ?
C20 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C20 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N1 C20 C21 107.6(3) . . ?
N1 C20 C19 121.5(3) . . ?
C21 C20 C19 130.9(3) . . ?
C22 C21 C20 106.2(3) . . ?
C22 C21 C26 125.6(3) . . ?
C20 C21 C26 128.2(3) . . ?
N2 C22 C21 107.4(3) . . ?
N2 C22 C23 120.7(3) . . ?
C21 C22 C23 131.9(3) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C27 C26 C25 105.9(3) . . ?
C27 C26 C21 126.6(3) . . ?
C25 C26 C21 127.4(3) . . ?
N3 C25 C26 106.8(4) . . ?
N3 C25 C24 121.9(4) . . ?
C26 C25 C24 131.2(4) . . ?
C25 C24 H24A 109.5 . . ?
C25 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C25 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
N4 C27 C26 108.0(4) . . ?
N4 C27 C28 120.7(4) . . ?
C26 C27 C28 131.3(4) . . ?
O13 C29 H29A 109.5 . . ?
O13 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
O13 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 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
C20 N1 N2 C22 -0.3(4) . . . . ?
C25 N3 N4 C27 0.2(5) . . . . ?
C6 C1 C2 C3 0.4(5) . . . . ?
C7 C1 C2 C3 -179.4(3) . . . . ?
C1 C2 C3 C4 -1.0(5) . . . . ?
C1 C2 C3 C8 -178.9(3) . . . . ?
C2 C3 C4 C5 0.8(5) . . . . ?
C8 C3 C4 C5 178.7(3) . . . . ?
C3 C4 C5 C6 0.0(5) . . . . ?
C3 C4 C5 C9 -178.1(3) . . . . ?
C2 C1 C6 C5 0.4(5) . . . . ?
C7 C1 C6 C5 -179.8(3) . . . . ?
C4 C5 C6 C1 -0.6(5) . . . . ?
C9 C5 C6 C1 177.6(3) . . . . ?
C6 C1 C7 O2 -2.2(5) . . . . ?
C2 C1 C7 O2 177.6(3) . . . . ?
C6 C1 C7 O1 177.6(3) . . . . ?
C2 C1 C7 O1 -2.6(5) . . . . ?
C2 C3 C8 O4 178.4(3) . . . . ?
C4 C3 C8 O4 0.5(5) . . . . ?
C2 C3 C8 O3 -0.5(5) . . . . ?
C4 C3 C8 O3 -178.4(3) . . . . ?
C6 C5 C9 O6 -179.5(3) . . . . ?
C4 C5 C9 O6 -1.4(6) . . . . ?
C6 C5 C9 O5 0.5(5) . . . . ?
C4 C5 C9 O5 178.6(3) . . . . ?
C15 C10 C11 C12 0.4(5) . . . . ?
C16 C10 C11 C12 177.4(3) . . . . ?
C10 C11 C12 C13 0.6(5) . . . . ?
C10 C11 C12 C17 -179.9(3) . . . . ?
C11 C12 C13 C14 -1.2(5) . . . . ?
C17 C12 C13 C14 179.3(3) . . . . ?
C12 C13 C14 C15 0.8(5) . . . . ?
C12 C13 C14 C18 -179.8(3) . . . . ?
C11 C10 C15 C14 -0.8(5) . . . . ?
C16 C10 C15 C14 -177.9(3) . . . . ?
C13 C14 C15 C10 0.2(5) . . . . ?
C18 C14 C15 C10 -179.3(3) . . . . ?
C15 C10 C16 O8 -7.0(5) . . . . ?
C11 C10 C16 O8 176.0(4) . . . . ?
C15 C10 C16 O7 171.1(3) . . . . ?
C11 C10 C16 O7 -5.9(5) . . . . ?
C11 C12 C17 O10 -176.1(3) . . . . ?
C13 C12 C17 O10 3.4(5) . . . . ?
C11 C12 C17 O9 3.1(5) . . . . ?
C13 C12 C17 O9 -177.4(3) . . . . ?
C15 C14 C18 O11 175.5(3) . . . . ?
C13 C14 C18 O11 -4.0(5) . . . . ?
C15 C14 C18 O12 -4.3(5) . . . . ?
C13 C14 C18 O12 176.3(3) . . . . ?
N2 N1 C20 C21 -0.2(4) . . . . ?
N2 N1 C20 C19 -179.5(3) . . . . ?
N1 C20 C21 C22 0.6(4) . . . . ?
C19 C20 C21 C22 179.8(4) . . . . ?
N1 C20 C21 C26 179.9(4) . . . . ?
C19 C20 C21 C26 -0.9(7) . . . . ?
N1 N2 C22 C21 0.6(4) . . . . ?
N1 N2 C22 C23 -179.3(3) . . . . ?
C20 C21 C22 N2 -0.7(4) . . . . ?
C26 C21 C22 N2 179.9(3) . . . . ?
C20 C21 C22 C23 179.2(4) . . . . ?
C26 C21 C22 C23 -0.2(7) . . . . ?
C22 C21 C26 C27 -56.9(6) . . . . ?
C20 C21 C26 C27 123.8(5) . . . . ?
C22 C21 C26 C25 118.2(5) . . . . ?
C20 C21 C26 C25 -61.0(6) . . . . ?
N4 N3 C25 C26 0.0(4) . . . . ?
N4 N3 C25 C24 -179.7(4) . . . . ?
C27 C26 C25 N3 -0.2(4) . . . . ?
C21 C26 C25 N3 -176.1(4) . . . . ?
C27 C26 C25 C24 179.5(4) . . . . ?
C21 C26 C25 C24 3.5(7) . . . . ?
N3 N4 C27 C26 -0.3(4) . . . . ?
N3 N4 C27 C28 -178.6(4) . . . . ?
C25 C26 C27 N4 0.3(4) . . . . ?
C21 C26 C27 N4 176.3(4) . . . . ?
C25 C26 C27 C28 178.4(4) . . . . ?
C21 C26 C27 C28 -5.6(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.779
_refine_diff_density_min         -0.707
_refine_diff_density_rms         0.093
