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

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

data_f
_database_code_depnum_ccdc_archive 'CCDC 1425998'
_audit_update_record             
;
2015-09-21 deposited with the CCDC.
2016-06-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        'Diethanolammonium Picrate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H2 N3 O7, C8 H19 02 N, H2O'
_chemical_formula_sum            'C14 H22 N4 O10'
_chemical_formula_weight         406.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c
_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                   13.5048(2)
_cell_length_b                   19.1864(3)
_cell_length_c                   7.05670(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.400(2)
_cell_angle_gamma                90.00
_cell_volume                     1827.91(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       'rod shape'
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          .45
_exptl_crystal_size_mid          .35
_exptl_crystal_size_min          .35
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             856
_exptl_absorpt_coefficient_mu    1.095
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  .663
_exptl_absorpt_correction_T_max  .682
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  w/
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9408
_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_av_sigmaI/netI    0.0181
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         3.27
_diffrn_reflns_theta_max         66.59
_reflns_number_total             3202
_reflns_number_gt                3056
_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)+(0.0616P)²+1.0555P] 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         3202
_refine_ls_number_parameters     256
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0413
_refine_ls_wR_factor_ref         0.1145
_refine_ls_wR_factor_gt          0.1129
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_restrained_S_all      1.120
_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
O7 O 0.60566(8) 0.19865(6) 0.21818(17) 0.0191(3) Uani 1 1 d . . .
O8 O 0.44702(8) 0.12004(6) 0.11369(17) 0.0215(3) Uani 1 1 d . . .
H9 H 0.5064 0.1306 0.1379 0.032 Uiso 1 1 calc R . .
O9 O 0.27681(9) 0.23470(6) 0.67636(18) 0.0234(3) Uani 1 1 d . . .
H8 H 0.3313 0.2462 0.7271 0.035 Uiso 1 1 calc R . .
O10 O 0.44339(8) 0.25915(6) -0.09367(14) 0.0198(3) Uani 1 1 d G . .
H10E H 0.4995 0.2612 -0.1453 0.030 Uiso 1 1 d G . .
H10D H 0.4415 0.2237 -0.0217 0.030 Uiso 1 1 d G . .
N4 N 0.33465(9) 0.11627(6) 0.46751(15) 0.0129(3) Uani 1 1 d G . .
H4B H 0.3624 0.1597 0.4443 0.015 Uiso 1 1 calc R . .
O6 O 0.65706(9) 0.06637(6) 0.1317(2) 0.0272(3) Uani 1 1 d . . .
O3 O 1.01525(9) 0.31856(7) -0.0139(2) 0.0286(3) Uani 1 1 d . . .
O2 O 0.68362(9) 0.39436(6) 0.05954(19) 0.0262(3) Uani 1 1 d . . .
N1 N 0.66333(10) 0.34156(7) 0.1510(2) 0.0152(3) Uani 1 1 d . . .
O1 O 0.59139(9) 0.33791(6) 0.25213(19) 0.0265(3) Uani 1 1 d . . .
O4 O 1.04780(9) 0.20807(7) -0.0204(2) 0.0346(4) Uani 1 1 d . . .
C4 C 0.86321(12) 0.17360(8) 0.0909(2) 0.0152(3) Uani 1 1 d . . .
H4 H 0.9099 0.1369 0.0789 0.018 Uiso 1 1 calc R . .
N2 N 0.99168(10) 0.25721(8) 0.0062(2) 0.0198(3) Uani 1 1 d . . .
N3 N 0.74245(10) 0.08556(7) 0.1595(2) 0.0168(3) Uani 1 1 d . . .
O5 O 0.81064(9) 0.04545(7) 0.2003(2) 0.0303(3) Uani 1 1 d . . .
C7 C 0.23957(11) 0.11279(8) 0.3513(2) 0.0142(3) Uani 1 1 d . . .
H7A H 0.2548 0.1192 0.2159 0.017 Uiso 1 1 calc R . .
H7B H 0.1959 0.1516 0.3890 0.017 Uiso 1 1 calc R . .
C2 C 0.69172(11) 0.21194(8) 0.1675(2) 0.0132(3) Uani 1 1 d . . .
C3 C 0.76692(12) 0.15932(8) 0.1369(2) 0.0143(3) Uani 1 1 d . . .
C8 C 0.18467(12) 0.04443(8) 0.3744(2) 0.0165(3) Uani 1 1 d . . .
H8A H 0.1615 0.0406 0.5060 0.020 Uiso 1 1 calc R . .
H8B H 0.2305 0.0052 0.3517 0.020 Uiso 1 1 calc R . .
C13 C 0.31915(12) 0.11231(8) 0.6789(2) 0.0161(3) Uani 1 1 d . . .
H13A H 0.3837 0.1178 0.7468 0.019 Uiso 1 1 calc R . .
H13B H 0.2923 0.0659 0.7110 0.019 Uiso 1 1 calc R . .
C12 C 0.42459(12) 0.05567(9) 0.2020(3) 0.0206(4) Uani 1 1 d . . .
H12A H 0.4788 0.0222 0.1793 0.025 Uiso 1 1 calc R . .
H12B H 0.3632 0.0364 0.1432 0.025 Uiso 1 1 calc R . .
C1 C 0.72917(11) 0.28176(8) 0.1350(2) 0.0133(3) Uani 1 1 d . . .
C11 C 0.41094(11) 0.06290(8) 0.4145(2) 0.0170(3) Uani 1 1 d . . .
H11A H 0.3913 0.0171 0.4661 0.020 Uiso 1 1 calc R . .
H11B H 0.4753 0.0758 0.4750 0.020 Uiso 1 1 calc R . .
C9 C 0.09605(13) 0.03924(9) 0.2368(3) 0.0206(4) Uani 1 1 d . . .
H9A H 0.0475 0.0761 0.2667 0.025 Uiso 1 1 calc R . .
H9B H 0.1184 0.0471 0.1060 0.025 Uiso 1 1 calc R . .
C6 C 0.82431(11) 0.29632(8) 0.0819(2) 0.0146(3) Uani 1 1 d . . .
H6 H 0.8440 0.3430 0.0589 0.018 Uiso 1 1 calc R . .
C5 C 0.89106(11) 0.24209(9) 0.0625(2) 0.0149(3) Uani 1 1 d . . .
C14 C 0.24845(12) 0.16828(9) 0.7444(2) 0.0206(4) Uani 1 1 d . . .
H14A H 0.1805 0.1573 0.6975 0.025 Uiso 1 1 calc R . .
H14B H 0.2481 0.1690 0.8846 0.025 Uiso 1 1 calc R . .
C10 C 0.04613(13) -0.03161(9) 0.2481(3) 0.0228(4) Uani 1 1 d . . .
H10A H 0.0924 -0.0679 0.2086 0.034 Uiso 1 1 calc R . .
H10B H -0.0128 -0.0322 0.1642 0.034 Uiso 1 1 calc R . .
H10C H 0.0266 -0.0404 0.3788 0.034 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
O7 C2 1.2506(19) . ?
O8 C12 1.419(2) . ?
O8 H9 0.8400 . ?
O9 C14 1.418(2) . ?
O9 H8 0.8400 . ?
O10 H10E 0.8501 . ?
O10 H10D 0.8499 . ?
N4 C11 1.5062(19) . ?
N4 C7 1.508(2) . ?
N4 C13 1.5133(18) . ?
N4 H4B 0.9300 . ?
O6 N3 1.2216(19) . ?
O3 N2 1.228(2) . ?
O2 N1 1.2354(18) . ?
N1 O1 1.2216(18) . ?
N1 C1 1.458(2) . ?
O4 N2 1.227(2) . ?
C4 C3 1.375(2) . ?
C4 C5 1.383(2) . ?
C4 H4 0.9500 . ?
N2 C5 1.454(2) . ?
N3 O5 1.2291(19) . ?
N3 C3 1.463(2) . ?
C7 C8 1.517(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C2 C3 1.452(2) . ?
C2 C1 1.452(2) . ?
C8 C9 1.526(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C13 C14 1.516(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C12 C11 1.522(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C1 C6 1.376(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C9 C10 1.520(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C6 C5 1.386(2) . ?
C6 H6 0.9500 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 O8 H9 109.5 . . ?
C14 O9 H8 109.5 . . ?
H10E O10 H10D 109.5 . . ?
C11 N4 C7 114.41(12) . . ?
C11 N4 C13 108.82(11) . . ?
C7 N4 C13 113.43(11) . . ?
C11 N4 H4B 106.5 . . ?
C7 N4 H4B 106.5 . . ?
C13 N4 H4B 106.5 . . ?
O1 N1 O2 122.82(13) . . ?
O1 N1 C1 119.70(13) . . ?
O2 N1 C1 117.48(13) . . ?
C3 C4 C5 119.05(14) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
O4 N2 O3 123.77(14) . . ?
O4 N2 C5 118.25(14) . . ?
O3 N2 C5 117.98(14) . . ?
O6 N3 O5 123.22(14) . . ?
O6 N3 C3 119.27(13) . . ?
O5 N3 C3 117.47(13) . . ?
N4 C7 C8 113.05(12) . . ?
N4 C7 H7A 109.0 . . ?
C8 C7 H7A 109.0 . . ?
N4 C7 H7B 109.0 . . ?
C8 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
O7 C2 C3 124.00(14) . . ?
O7 C2 C1 124.26(14) . . ?
C3 C2 C1 111.74(13) . . ?
C4 C3 C2 124.43(14) . . ?
C4 C3 N3 115.84(14) . . ?
C2 C3 N3 119.72(13) . . ?
C7 C8 C9 111.46(13) . . ?
C7 C8 H8A 109.3 . . ?
C9 C8 H8A 109.3 . . ?
C7 C8 H8B 109.3 . . ?
C9 C8 H8B 109.3 . . ?
H8A C8 H8B 108.0 . . ?
N4 C13 C14 111.59(13) . . ?
N4 C13 H13A 109.3 . . ?
C14 C13 H13A 109.3 . . ?
N4 C13 H13B 109.3 . . ?
C14 C13 H13B 109.3 . . ?
H13A C13 H13B 108.0 . . ?
O8 C12 C11 112.68(13) . . ?
O8 C12 H12A 109.1 . . ?
C11 C12 H12A 109.1 . . ?
O8 C12 H12B 109.1 . . ?
C11 C12 H12B 109.1 . . ?
H12A C12 H12B 107.8 . . ?
C6 C1 C2 124.16(14) . . ?
C6 C1 N1 115.90(14) . . ?
C2 C1 N1 119.89(13) . . ?
N4 C11 C12 114.01(13) . . ?
N4 C11 H11A 108.8 . . ?
C12 C11 H11A 108.8 . . ?
N4 C11 H11B 108.8 . . ?
C12 C11 H11B 108.8 . . ?
H11A C11 H11B 107.6 . . ?
C10 C9 C8 111.54(14) . . ?
C10 C9 H9A 109.3 . . ?
C8 C9 H9A 109.3 . . ?
C10 C9 H9B 109.3 . . ?
C8 C9 H9B 109.3 . . ?
H9A C9 H9B 108.0 . . ?
C1 C6 C5 119.25(15) . . ?
C1 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
C4 C5 C6 121.28(14) . . ?
C4 C5 N2 119.24(14) . . ?
C6 C5 N2 119.46(15) . . ?
O9 C14 C13 110.86(13) . . ?
O9 C14 H14A 109.5 . . ?
C13 C14 H14A 109.5 . . ?
O9 C14 H14B 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        66.59
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.052
####################################################################### 
# 
# 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_f
_database_code_depnum_ccdc_archive 'CCDC 1425999'
_audit_update_record             
;
2015-09-21 deposited with the CCDC.
2016-06-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H23 N4 O10'
_chemical_formula_weight         407.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

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                   13.5233(2)
_cell_length_b                   19.2674(2)
_cell_length_c                   7.10340(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.5850(10)
_cell_angle_gamma                90.00
_cell_volume                     1850.15(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    185(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       rod
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             860
_exptl_absorpt_coefficient_mu    1.082
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6416
_exptl_absorpt_correction_T_max  0.8126
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      185(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  w/
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9619
_diffrn_reflns_av_R_equivalents  0.0377
_diffrn_reflns_av_sigmaI/netI    0.0291
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         3.27
_diffrn_reflns_theta_max         66.59
_reflns_number_total             3276
_reflns_number_gt                2975
_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)+(0.1004P)²+0.7960P] 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         3276
_refine_ls_number_parameters     274
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0586
_refine_ls_wR_factor_ref         0.1621
_refine_ls_wR_factor_gt          0.1583
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.003
_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
O7 O 0.89710(10) 0.19898(7) 0.2800(2) 0.0374(4) Uani 1 1 d . A .
N1 N 0.83734(13) 0.34103(8) 0.3389(2) 0.0303(4) Uani 1 1 d . . .
C4 C 0.64064(14) 0.17291(10) 0.4059(3) 0.0273(4) Uani 1 1 d . . .
H4 H 0.5946 0.1362 0.4199 0.033 Uiso 1 1 calc R . .
C3 C 0.73701(14) 0.15892(9) 0.3588(3) 0.0261(4) Uani 1 1 d . A .
O3 O 0.48756(12) 0.31601(9) 0.5093(3) 0.0518(5) Uani 1 1 d . . .
C2 C 0.81086(14) 0.21177(9) 0.3276(3) 0.0257(4) Uani 1 1 d . . .
N3 N 0.76188(13) 0.08597(8) 0.3371(3) 0.0330(4) Uani 1 1 d . . .
N2 N 0.51156(13) 0.25538(10) 0.4886(3) 0.0356(4) Uani 1 1 d . . .
O1 O 0.91062(14) 0.33720(8) 0.2501(3) 0.0606(6) Uani 1 1 d . A .
C1 C 0.77275(14) 0.28100(9) 0.3582(3) 0.0256(4) Uani 1 1 d . A .
O2B O 0.81616(15) 0.39377(9) 0.4307(4) 0.0491(9) Uani 0.851(8) 1 d P A 2
O4 O 0.45673(13) 0.20612(10) 0.5164(3) 0.0615(6) Uani 1 1 d . . .
C5 C 0.61215(14) 0.24073(10) 0.4323(3) 0.0271(4) Uani 1 1 d . A .
C6 C 0.67739(14) 0.29524(10) 0.4102(3) 0.0280(4) Uani 1 1 d . . .
H6 H 0.6568 0.3417 0.4304 0.034 Uiso 1 1 calc R A .
O5B O 0.84697(14) 0.06690(9) 0.3585(4) 0.0495(9) Uani 0.855(8) 1 d P A 2
O6B O 0.69380(17) 0.04502(10) 0.3049(5) 0.0561(12) Uani 0.880(10) 1 d P A 2
O9 O 0.05644(11) 0.12023(9) 0.3858(2) 0.0405(4) Uani 1 1 d . . .
H9 H -0.0012 0.1325 0.3536 0.061 Uiso 1 1 calc R . .
N4 N 0.16792(11) 0.11575(7) 0.0350(2) 0.0241(4) Uani 1 1 d . . .
H4A H 0.1405 0.1590 0.0587 0.029 Uiso 1 1 calc R . .
O8 O 0.22583(14) 0.23365(8) -0.1758(3) 0.0505(5) Uani 1 1 d . . .
H8 H 0.1732 0.2464 -0.2312 0.076 Uiso 1 1 calc R . .
C7 C 0.26313(14) 0.11224(9) 0.1494(3) 0.0268(4) Uani 1 1 d . . .
H7A H 0.2485 0.1191 0.2839 0.032 Uiso 1 1 calc R . .
H7B H 0.3068 0.1507 0.1108 0.032 Uiso 1 1 calc R . .
C8 C 0.31770(14) 0.04406(10) 0.1278(3) 0.0298(4) Uani 1 1 d . . .
H8A H 0.2725 0.0052 0.1555 0.036 Uiso 1 1 calc R . .
H8B H 0.3384 0.0391 -0.0041 0.036 Uiso 1 1 calc R . .
C11 C 0.18183(15) 0.11215(10) -0.1742(3) 0.0303(4) Uani 1 1 d . . .
H11A H 0.1170 0.1181 -0.2402 0.036 Uiso 1 1 calc R . .
H11B H 0.2077 0.0658 -0.2070 0.036 Uiso 1 1 calc R . .
C13 C 0.09169(14) 0.06287(10) 0.0889(3) 0.0305(4) Uani 1 1 d . . .
H13A H 0.1110 0.0171 0.0383 0.037 Uiso 1 1 calc R . .
H13B H 0.0273 0.0757 0.0289 0.037 Uiso 1 1 calc R . .
C9 C 0.40790(17) 0.03987(11) 0.2583(3) 0.0378(5) Uani 1 1 d . . .
H9A H 0.4558 0.0761 0.2229 0.045 Uiso 1 1 calc R . .
H9B H 0.3880 0.0492 0.3890 0.045 Uiso 1 1 calc R . .
C12 C 0.25288(17) 0.16751(13) -0.2414(3) 0.0403(5) Uani 1 1 d . . .
H12A H 0.3208 0.1564 -0.1952 0.048 Uiso 1 1 calc R . .
H12B H 0.2527 0.1678 -0.3807 0.048 Uiso 1 1 calc R . .
C14 C 0.07860(16) 0.05611(11) 0.2990(3) 0.0381(5) Uani 1 1 d . . .
H14A H 0.0245 0.0228 0.3222 0.046 Uiso 1 1 calc R . .
H14B H 0.1401 0.0370 0.3576 0.046 Uiso 1 1 calc R . .
O10 O 0.06039(11) 0.24025(7) 0.0929(2) 0.0408(4) Uani 1 1 d G . .
H10D H 0.0031 0.2363 0.1383 0.061 Uiso 1 1 d G . .
H10E H 0.0644 0.2788 0.0352 0.061 Uiso 1 1 d G . .
C10 C 0.45744(14) -0.03045(10) 0.2508(3) 0.0419(5) Uani 1 1 d G . .
H10A H 0.4120 -0.0661 0.2957 0.063 Uiso 1 1 calc R . .
H10B H 0.5175 -0.0301 0.3311 0.063 Uiso 1 1 calc R . .
H10C H 0.4748 -0.0408 0.1208 0.063 Uiso 1 1 calc R . .
O2A O 0.8011(8) 0.3974(5) 0.2844(17) 0.040(4) Uiso 0.152(8) 1 d P A 1
O5A O 0.8333(9) 0.0741(7) 0.217(2) 0.043(5) Uiso 0.133(8) 1 d P A 1
O6A O 0.7249(11) 0.0424(7) 0.421(3) 0.042(5) Uiso 0.129(10) 1 d P A 1


_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
O7 C2 1.248(2) . ?
N1 O1 1.191(2) . ?
N1 O2B 1.245(2) . ?
N1 O2A 1.249(11) . ?
N1 C1 1.458(2) . ?
C4 C5 1.377(3) . ?
C4 C3 1.381(3) . ?
C3 C2 1.448(3) . ?
C3 N3 1.454(2) . ?
O3 N2 1.222(2) . ?
C2 C1 1.449(2) . ?
N3 O6A 1.150(13) . ?
N3 O5B 1.214(3) . ?
N3 O6B 1.229(3) . ?
N3 O5A 1.327(13) . ?
N2 O4 1.224(3) . ?
N2 C5 1.456(2) . ?
C1 C6 1.379(3) . ?
C5 C6 1.383(3) . ?
O9 C14 1.416(3) . ?
N4 C11 1.505(2) . ?
N4 C7 1.505(2) . ?
N4 C13 1.506(2) . ?
O8 C12 1.409(3) . ?
C7 C8 1.517(3) . ?
C8 C9 1.514(3) . ?
C11 C12 1.521(3) . ?
C13 C14 1.513(3) . ?
C9 C10 1.513(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 N1 O2B 122.31(18) . . ?
O1 N1 O2A 102.4(5) . . ?
O2B N1 O2A 50.1(5) . . ?
O1 N1 C1 120.66(16) . . ?
O2B N1 C1 116.80(17) . . ?
O2A N1 C1 119.3(5) . . ?
C5 C4 C3 119.19(17) . . ?
C4 C3 C2 124.02(17) . . ?
C4 C3 N3 115.89(16) . . ?
C2 C3 N3 120.07(17) . . ?
O7 C2 C3 123.82(17) . . ?
O7 C2 C1 124.17(17) . . ?
C3 C2 C1 112.01(16) . . ?
O6A N3 O5B 98.0(8) . . ?
O6A N3 O6B 45.1(9) . . ?
O5B N3 O6B 122.11(19) . . ?
O6A N3 O5A 122.7(9) . . ?
O5B N3 O5A 47.4(6) . . ?
O6B N3 O5A 108.9(6) . . ?
O6A N3 C3 123.1(7) . . ?
O5B N3 C3 120.04(17) . . ?
O6B N3 C3 117.77(19) . . ?
O5A N3 C3 114.2(6) . . ?
O3 N2 O4 123.89(18) . . ?
O3 N2 C5 118.14(18) . . ?
O4 N2 C5 117.95(18) . . ?
C6 C1 C2 124.25(17) . . ?
C6 C1 N1 115.76(16) . . ?
C2 C1 N1 119.98(17) . . ?
C4 C5 C6 121.56(18) . . ?
C4 C5 N2 119.25(18) . . ?
C6 C5 N2 119.18(17) . . ?
C1 C6 C5 118.92(17) . . ?
C11 N4 C7 113.76(14) . . ?
C11 N4 C13 108.97(15) . . ?
C7 N4 C13 114.42(14) . . ?
N4 C7 C8 113.31(14) . . ?
C9 C8 C7 111.74(16) . . ?
N4 C11 C12 112.01(16) . . ?
N4 C13 C14 114.11(16) . . ?
C10 C9 C8 112.10(17) . . ?
O8 C12 C11 111.01(17) . . ?
O9 C14 C13 112.71(16) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        66.59
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.395
_refine_diff_density_min         -0.421
_refine_diff_density_rms         0.075
