# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_mother
_database_code_depnum_ccdc_archive 'CCDC 1831132'
_audit_update_record             
;
2018-03-20 deposited with the CCDC.
2018-06-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H7 N O4'
_chemical_formula_weight         181.15

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

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

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

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

_cell_length_a                   7.611(15)
_cell_length_b                   10.47(2)
_cell_length_c                   10.55(2)
_cell_angle_alpha                89.45(3)
_cell_angle_beta                 81.87(3)
_cell_angle_gamma                76.75(3)
_cell_volume                     810(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298
_cell_measurement_reflns_used    1148
_cell_measurement_theta_min      2.7595
_cell_measurement_theta_max      23.494

_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.485
_exptl_crystal_F_000             376
_exptl_transmission_factor_min   0.6492
_exptl_transmission_factor_max   0.7454
_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.269
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.121
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART Breeze'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3745
_diffrn_reflns_av_unetI/netI     0.0510
_diffrn_reflns_av_R_equivalents  0.0177
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         1.999
_diffrn_reflns_theta_max         25.021
_diffrn_reflns_theta_full        25.021
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measured_fraction_theta_full 0.961
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_Laue_measured_fraction_full 0.961
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_point_group_measured_fraction_full 0.961
_reflns_number_total             2755
_reflns_number_gt                1670
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0863P)²+0.2473P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2755
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1034
_refine_ls_R_factor_gt           0.0601
_refine_ls_wR_factor_ref         0.1786
_refine_ls_wR_factor_gt          0.1588
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O5 O 0.7219(3) 0.4794(3) 0.4327(2) 0.0568(7) Uani 1 1 d . . . . .
H5 H 0.6407 0.5039 0.4930 0.085 Uiso 1 1 calc R U . . .
O6 O 0.4817(3) 0.4693(3) 0.3410(2) 0.0601(8) Uani 1 1 d . . . . .
O1 O 0.3254(3) 0.9839(3) 0.9242(2) 0.0667(8) Uani 1 1 d . . . . .
O3 O 0.8797(4) 0.7757(3) 0.4389(2) 0.0627(8) Uani 1 1 d . . . . .
O2 O 0.6191(3) 0.9415(3) 0.8497(2) 0.0727(9) Uani 1 1 d . . . . .
H2 H 0.6239 0.9657 0.9225 0.109 Uiso 1 1 calc R U . . .
O4 O 0.7162(4) 0.7558(3) 0.2935(2) 0.0703(9) Uani 1 1 d . . . . .
N1 N 0.7324(4) 0.7819(3) 0.4035(3) 0.0454(8) Uani 1 1 d . . . . .
O8 O 0.7695(4) 0.2514(3) -0.2017(3) 0.0856(10) Uani 1 1 d . . . . .
N2 N 0.6812(5) 0.2915(3) -0.0980(3) 0.0547(8) Uani 1 1 d . . . . .
O7 O 0.5166(4) 0.3025(3) -0.0726(3) 0.0867(10) Uani 1 1 d . . . . .
C5 C 0.5659(4) 0.8222(3) 0.4978(3) 0.0377(8) Uani 1 1 d . . . . .
C15 C 0.6541(4) 0.4578(3) 0.3380(3) 0.0371(8) Uani 1 1 d . . . . .
C10 C 0.9597(4) 0.3984(3) 0.1907(3) 0.0380(8) Uani 1 1 d . . . . .
C9 C 0.7699(4) 0.4119(3) 0.2125(3) 0.0353(8) Uani 1 1 d . . . . .
C7 C 0.4528(4) 0.9468(3) 0.8365(3) 0.0394(8) Uani 1 1 d . . . . .
C13 C 0.7783(5) 0.3292(3) -0.0001(3) 0.0404(8) Uani 1 1 d . . . . .
C1 C 0.4262(4) 0.9045(3) 0.7075(3) 0.0351(8) Uani 1 1 d . . . . .
C2 C 0.2518(4) 0.9064(3) 0.6734(3) 0.0387(8) Uani 1 1 d . . . . .
C6 C 0.5809(4) 0.8619(3) 0.6178(3) 0.0366(8) Uani 1 1 d . . . . .
H6 H 0.6955 0.8604 0.6397 0.044 Uiso 1 1 calc R U . . .
C14 C 0.6804(5) 0.3773(3) 0.1168(3) 0.0402(8) Uani 1 1 d . . . . .
H14 H 0.5547 0.3865 0.1313 0.048 Uiso 1 1 calc R U . . .
C12 C 0.9642(5) 0.3134(3) -0.0249(3) 0.0454(9) Uani 1 1 d . . . . .
H12 H 1.0290 0.2803 -0.1037 0.055 Uiso 1 1 calc R U . . .
C11 C 1.0517(5) 0.3484(3) 0.0712(3) 0.0459(9) Uani 1 1 d . . . . .
H11 H 1.1776 0.3380 0.0555 0.055 Uiso 1 1 calc R U . . .
C3 C 0.2467(5) 0.8643(3) 0.5496(3) 0.0466(9) Uani 1 1 d . . . . .
H3 H 0.1337 0.8644 0.5256 0.056 Uiso 1 1 calc R U . . .
C8 C 0.0759(5) 0.9535(4) 0.7611(3) 0.0536(10) Uani 1 1 d . . . . .
H8A H 0.0625 1.0440 0.7846 0.080 Uiso 1 1 calc R U . . .
H8B H 0.0765 0.9018 0.8367 0.080 Uiso 1 1 calc R U . . .
H8C H -0.0241 0.9450 0.7182 0.080 Uiso 1 1 calc R U . . .
C4 C 0.4000(5) 0.8226(3) 0.4608(3) 0.0469(9) Uani 1 1 d . . . . .
H4 H 0.3915 0.7956 0.3786 0.056 Uiso 1 1 calc R U . . .
C16 C 1.0669(5) 0.4353(4) 0.2874(3) 0.0561(10) Uani 1 1 d . . . . .
H16A H 1.1939 0.4166 0.2525 0.084 Uiso 1 1 calc R U . . .
H16B H 1.0505 0.3857 0.3633 0.084 Uiso 1 1 calc R U . . .
H16C H 1.0251 0.5273 0.3083 0.084 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O5 C15 1.233(4) . ?
O5 H5 0.8200 . ?
O6 C15 1.285(5) . ?
O1 C7 1.236(4) . ?
O3 N1 1.219(4) . ?
O2 C7 1.281(5) . ?
O2 H2 0.8200 . ?
O4 N1 1.225(4) . ?
N1 C5 1.477(5) . ?
O8 N2 1.223(4) . ?
N2 O7 1.222(5) . ?
N2 C13 1.458(5) . ?
C5 C6 1.364(5) . ?
C5 C4 1.372(5) . ?
C15 C9 1.499(5) . ?
C10 C11 1.397(5) . ?
C10 C9 1.404(5) . ?
C10 C16 1.498(5) . ?
C9 C14 1.390(5) . ?
C7 C1 1.490(5) . ?
C13 C12 1.373(5) . ?
C13 C14 1.382(5) . ?
C1 C6 1.391(5) . ?
C1 C2 1.420(5) . ?
C2 C3 1.391(5) . ?
C2 C8 1.500(5) . ?
C6 H6 0.9300 . ?
C14 H14 0.9300 . ?
C12 C11 1.385(5) . ?
C12 H12 0.9300 . ?
C11 H11 0.9300 . ?
C3 C4 1.377(5) . ?
C3 H3 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C4 H4 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 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
C15 O5 H5 109.5 . . ?
C7 O2 H2 109.5 . . ?
O3 N1 O4 123.0(3) . . ?
O3 N1 C5 118.5(3) . . ?
O4 N1 C5 118.5(3) . . ?
O7 N2 O8 123.6(3) . . ?
O7 N2 C13 118.4(3) . . ?
O8 N2 C13 117.9(4) . . ?
C6 C5 C4 122.0(3) . . ?
C6 C5 N1 119.1(3) . . ?
C4 C5 N1 118.9(3) . . ?
O5 C15 O6 122.6(3) . . ?
O5 C15 C9 121.5(3) . . ?
O6 C15 C9 115.9(3) . . ?
C11 C10 C9 117.4(3) . . ?
C11 C10 C16 118.8(3) . . ?
C9 C10 C16 123.8(3) . . ?
C14 C9 C10 120.1(3) . . ?
C14 C9 C15 116.3(3) . . ?
C10 C9 C15 123.5(3) . . ?
O1 C7 O2 122.4(3) . . ?
O1 C7 C1 123.0(3) . . ?
O2 C7 C1 114.6(3) . . ?
C12 C13 C14 121.7(3) . . ?
C12 C13 N2 119.5(3) . . ?
C14 C13 N2 118.8(3) . . ?
C6 C1 C2 119.5(3) . . ?
C6 C1 C7 117.6(3) . . ?
C2 C1 C7 123.0(3) . . ?
C3 C2 C1 117.0(3) . . ?
C3 C2 C8 119.0(3) . . ?
C1 C2 C8 124.0(3) . . ?
C5 C6 C1 120.5(3) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
C13 C14 C9 120.0(3) . . ?
C13 C14 H14 120.0 . . ?
C9 C14 H14 120.0 . . ?
C13 C12 C11 117.7(3) . . ?
C13 C12 H12 121.1 . . ?
C11 C12 H12 121.1 . . ?
C12 C11 C10 123.0(3) . . ?
C12 C11 H11 118.5 . . ?
C10 C11 H11 118.5 . . ?
C4 C3 C2 123.5(3) . . ?
C4 C3 H3 118.2 . . ?
C2 C3 H3 118.2 . . ?
C2 C8 H8A 109.5 . . ?
C2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C5 C4 C3 117.6(3) . . ?
C5 C4 H4 121.2 . . ?
C3 C4 H4 121.2 . . ?
C10 C16 H16A 109.5 . . ?
C10 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C10 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

_refine_diff_density_max         0.233
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.056

####################################################################### 
# 
# 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_twinned
_database_code_depnum_ccdc_archive 'CCDC 1831133'
_audit_update_record             
;
2018-03-20 deposited with the CCDC.
2018-06-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H7 N O4'
_chemical_formula_weight         181.15

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

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

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

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

_cell_length_a                   7.636(13)
_cell_length_b                   10.426(19)
_cell_length_c                   10.520(18)
_cell_angle_alpha                89.28(3)
_cell_angle_beta                 81.80(3)
_cell_angle_gamma                76.32(3)
_cell_volume                     805(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    298
_cell_measurement_reflns_used    859
_cell_measurement_theta_min      2.774
_cell_measurement_theta_max      21.9785

_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_F_000             376
_exptl_transmission_factor_min   0.5913
_exptl_transmission_factor_max   0.7454
_exptl_crystal_size_max          0.269
_exptl_crystal_size_mid          0.215
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.122
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART Breeze'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3821
_diffrn_reflns_av_unetI/netI     0.0999
_diffrn_reflns_av_R_equivalents  0.0488
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.956
_diffrn_reflns_theta_max         25.025
_diffrn_reflns_theta_full        25.025
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measured_fraction_theta_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_point_group_measured_fraction_full 0.969
_reflns_number_total             2769
_reflns_number_gt                1500
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2769
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1523
_refine_ls_R_factor_gt           0.1016
_refine_ls_wR_factor_ref         0.3546
_refine_ls_wR_factor_gt          0.3201
_refine_ls_goodness_of_fit_ref   1.161
_refine_ls_restrained_S_all      1.161
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O5 O 0.7211(6) 0.4793(5) 0.4318(4) 0.0586(13) Uani 1 1 d . . . . .
H5 H 0.6396 0.5037 0.4923 0.088 Uiso 1 1 calc R U . . .
O6 O 0.4816(5) 0.4691(5) 0.3407(4) 0.0623(14) Uani 1 1 d . . . . .
O1 O 0.3263(6) 0.9835(5) 0.9250(4) 0.0684(15) Uani 1 1 d . . . . .
O3 O 0.8798(6) 0.7759(5) 0.4392(4) 0.0641(14) Uani 1 1 d . . . . .
O2 O 0.6191(6) 0.9421(6) 0.8502(4) 0.0758(17) Uani 1 1 d . . . . .
H2 H 0.6235 0.9661 0.9233 0.114 Uiso 1 1 calc R U . . .
O4 O 0.7164(7) 0.7556(5) 0.2929(4) 0.0714(15) Uani 1 1 d . . . . .
N1 N 0.7321(7) 0.7814(5) 0.4036(5) 0.0479(13) Uani 1 1 d . . . . .
O8 O 0.7693(7) 0.2508(6) -0.2008(4) 0.0871(19) Uani 1 1 d . . . . .
N2 N 0.6813(8) 0.2916(6) -0.0984(5) 0.0572(15) Uani 1 1 d . . . . .
O7 O 0.5165(7) 0.3014(6) -0.0725(5) 0.0905(19) Uani 1 1 d . . . . .
C5 C 0.5642(8) 0.8226(5) 0.4975(5) 0.0385(13) Uani 1 1 d . . . . .
C15 C 0.6543(7) 0.4569(6) 0.3366(5) 0.0399(14) Uani 1 1 d . . . . .
C10 C 0.9606(7) 0.3983(6) 0.1905(5) 0.0399(14) Uani 1 1 d . . . . .
C9 C 0.7694(7) 0.4113(5) 0.2128(5) 0.0374(13) Uani 1 1 d . . . . .
C7 C 0.4533(8) 0.9465(6) 0.8372(5) 0.0419(15) Uani 1 1 d . . . . .
C13 C 0.7781(8) 0.3298(6) 0.0007(5) 0.0451(15) Uani 1 1 d . . . . .
C1 C 0.4263(7) 0.9047(5) 0.7072(5) 0.0363(13) Uani 1 1 d . . . . .
C2 C 0.2522(7) 0.9064(6) 0.6732(5) 0.0401(14) Uani 1 1 d . . . . .
C6 C 0.5808(8) 0.8620(5) 0.6183(5) 0.0395(14) Uani 1 1 d . . . . .
H6 H 0.6952 0.8600 0.6402 0.047 Uiso 1 1 calc R U . . .
C14 C 0.6807(8) 0.3768(6) 0.1156(5) 0.0428(15) Uani 1 1 d . . . . .
H14 H 0.5552 0.3860 0.1297 0.051 Uiso 1 1 calc R U . . .
C12 C 0.9645(8) 0.3132(6) -0.0248(5) 0.0491(16) Uani 1 1 d . . . . .
H12 H 1.0291 0.2798 -0.1039 0.059 Uiso 1 1 calc R U . . .
C11 C 1.0515(8) 0.3477(6) 0.0702(5) 0.0473(16) Uani 1 1 d . . . . .
H11 H 1.1771 0.3368 0.0538 0.057 Uiso 1 1 calc R U . . .
C3 C 0.2475(8) 0.8642(6) 0.5505(6) 0.0483(16) Uani 1 1 d . . . . .
H3 H 0.1348 0.8638 0.5269 0.058 Uiso 1 1 calc R U . . .
C8 C 0.0746(8) 0.9536(7) 0.7624(6) 0.0553(17) Uani 1 1 d . . . . .
H8A H 0.0567 1.0459 0.7823 0.083 Uiso 1 1 calc R U . . .
H8B H 0.0789 0.9046 0.8402 0.083 Uiso 1 1 calc R U . . .
H8C H -0.0243 0.9404 0.7212 0.083 Uiso 1 1 calc R U . . .
C4 C 0.4002(9) 0.8227(6) 0.4608(6) 0.0506(16) Uani 1 1 d . . . . .
H4 H 0.3917 0.7957 0.3784 0.061 Uiso 1 1 calc R U . . .
C16 C 1.0673(9) 0.4352(7) 0.2871(6) 0.0557(17) Uani 1 1 d . . . . .
H16A H 1.1947 0.4121 0.2536 0.084 Uiso 1 1 calc R U . . .
H16B H 1.0465 0.3887 0.3650 0.084 Uiso 1 1 calc R U . . .
H16C H 1.0292 0.5286 0.3046 0.084 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O5 C15 1.235(7) . ?
O5 H5 0.8200 . ?
O6 C15 1.289(7) . ?
O1 C7 1.232(7) . ?
O3 N1 1.226(7) . ?
O2 C7 1.282(7) . ?
O2 H2 0.8200 . ?
O4 N1 1.228(6) . ?
N1 C5 1.481(8) . ?
O8 N2 1.209(7) . ?
N2 O7 1.229(7) . ?
N2 C13 1.470(8) . ?
C5 C4 1.362(9) . ?
C5 C6 1.372(8) . ?
C15 C9 1.479(8) . ?
C10 C11 1.399(8) . ?
C10 C9 1.419(8) . ?
C10 C16 1.496(8) . ?
C9 C14 1.399(8) . ?
C7 C1 1.497(8) . ?
C13 C14 1.357(8) . ?
C13 C12 1.380(9) . ?
C1 C6 1.383(8) . ?
C1 C2 1.421(8) . ?
C2 C3 1.377(8) . ?
C2 C8 1.515(8) . ?
C6 H6 0.9300 . ?
C14 H14 0.9300 . ?
C12 C11 1.371(8) . ?
C12 H12 0.9300 . ?
C11 H11 0.9300 . ?
C3 C4 1.377(9) . ?
C3 H3 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C4 H4 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 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
C15 O5 H5 109.5 . . ?
C7 O2 H2 109.5 . . ?
O3 N1 O4 123.0(5) . . ?
O3 N1 C5 118.9(5) . . ?
O4 N1 C5 118.1(5) . . ?
O8 N2 O7 123.7(6) . . ?
O8 N2 C13 117.9(6) . . ?
O7 N2 C13 118.4(5) . . ?
C4 C5 C6 122.6(5) . . ?
C4 C5 N1 119.4(5) . . ?
C6 C5 N1 118.0(5) . . ?
O5 C15 O6 121.9(5) . . ?
O5 C15 C9 121.5(5) . . ?
O6 C15 C9 116.6(5) . . ?
C11 C10 C9 116.8(5) . . ?
C11 C10 C16 119.3(5) . . ?
C9 C10 C16 124.0(5) . . ?
C14 C9 C10 119.9(5) . . ?
C14 C9 C15 116.4(5) . . ?
C10 C9 C15 123.7(5) . . ?
O1 C7 O2 122.3(5) . . ?
O1 C7 C1 122.8(5) . . ?
O2 C7 C1 114.8(5) . . ?
C14 C13 C12 122.4(5) . . ?
C14 C13 N2 118.5(5) . . ?
C12 C13 N2 119.1(5) . . ?
C6 C1 C2 119.9(5) . . ?
C6 C1 C7 117.0(5) . . ?
C2 C1 C7 123.1(5) . . ?
C3 C2 C1 117.0(5) . . ?
C3 C2 C8 119.0(5) . . ?
C1 C2 C8 124.1(5) . . ?
C5 C6 C1 119.5(5) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
C13 C14 C9 119.8(5) . . ?
C13 C14 H14 120.1 . . ?
C9 C14 H14 120.1 . . ?
C11 C12 C13 117.8(5) . . ?
C11 C12 H12 121.1 . . ?
C13 C12 H12 121.1 . . ?
C12 C11 C10 123.3(6) . . ?
C12 C11 H11 118.4 . . ?
C10 C11 H11 118.4 . . ?
C4 C3 C2 123.7(5) . . ?
C4 C3 H3 118.1 . . ?
C2 C3 H3 118.1 . . ?
C2 C8 H8A 109.5 . . ?
C2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C5 C4 C3 117.3(6) . . ?
C5 C4 H4 121.3 . . ?
C3 C4 H4 121.3 . . ?
C10 C16 H16A 109.5 . . ?
C10 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C10 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

_refine_diff_density_max         0.428
_refine_diff_density_min         -0.447
_refine_diff_density_rms         0.121

