# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_111
_database_code_depnum_ccdc_archive 'CCDC 1468837'
_audit_update_record             
;
2016-10-13 deposited with the CCDC.
2016-11-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H9 N2 O, C7 H4 N O4, C7 H5 N O4'
_chemical_formula_sum            'C24 H18 N4 O9'
_chemical_formula_weight         506.42

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'
_space_group_name_Hall           '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.3884(7)
_cell_length_b                   11.2382(10)
_cell_length_c                   14.8080(13)
_cell_angle_alpha                94.017(5)
_cell_angle_beta                 96.891(5)
_cell_angle_gamma                109.057(5)
_cell_volume                     1145.92(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1099
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      21.35

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             524
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.967
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_process_details   multi-scan

_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 and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8184
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_av_sigmaI/netI    0.0707
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.39
_diffrn_reflns_theta_max         25.25
_reflns_number_total             4150
_reflns_number_gt                2068
_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)+(0.0500P)²+0.0200P] 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         4150
_refine_ls_number_parameters     340
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1260
_refine_ls_R_factor_gt           0.0515
_refine_ls_wR_factor_ref         0.1284
_refine_ls_wR_factor_gt          0.1042
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_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
C2 C 0.7171(5) 0.7785(4) 0.5486(2) 0.0520(9) Uani 1 1 d . . .
C9 C 0.8983(5) 0.8641(3) 0.5946(2) 0.0474(9) Uani 1 1 d . . .
C8 C 0.9422(5) 0.9956(4) 0.6106(2) 0.0598(10) Uani 1 1 d . . .
H8 H 0.8496 1.0317 0.5912 0.072 Uiso 1 1 calc R . .
C1 C 0.5593(5) 0.8228(3) 0.5134(2) 0.0633(10) Uani 1 1 d . . .
H1 H 0.5722 0.9080 0.5230 0.076 Uiso 1 1 calc R . .
C5 C 1.2261(5) 0.8927(4) 0.6710(2) 0.0643(10) Uani 1 1 d . . .
H5 H 1.3201 0.8585 0.6917 0.077 Uiso 1 1 calc R . .
C10 C 1.0438(5) 0.8142(4) 0.6253(2) 0.0523(9) Uani 1 1 d . . .
C4 C 0.8374(6) 0.6068(4) 0.5687(3) 0.0746(12) Uani 1 1 d . . .
H4 H 0.8168 0.5204 0.5601 0.090 Uiso 1 1 calc R . .
C3 C 0.6915(5) 0.6518(4) 0.5376(2) 0.0744(12) Uani 1 1 d . . .
H3 H 0.5731 0.5949 0.5086 0.089 Uiso 1 1 calc R . .
C7 C 1.1207(6) 1.0710(3) 0.6546(2) 0.0699(11) Uani 1 1 d . . .
H7 H 1.1482 1.1581 0.6648 0.084 Uiso 1 1 calc R . .
C6 C 1.2622(5) 1.0195(4) 0.6844(2) 0.0723(11) Uani 1 1 d . . .
H6 H 1.3829 1.0727 0.7138 0.087 Uiso 1 1 calc R . .
C12 C 0.6764(5) 0.5753(3) 0.2487(3) 0.0497(9) Uani 1 1 d . . .
C17 C 0.6985(5) 0.5848(3) 0.1574(3) 0.0602(10) Uani 1 1 d . . .
C11 C 0.8014(5) 0.5307(4) 0.3161(2) 0.0599(10) Uani 1 1 d . . .
C13 C 0.5246(6) 0.6065(3) 0.2771(3) 0.0680(11) Uani 1 1 d . . .
H13 H 0.5043 0.6002 0.3376 0.082 Uiso 1 1 calc R . .
C15 C 0.4274(7) 0.6543(4) 0.1301(4) 0.0886(14) Uani 1 1 d . . .
H15 H 0.3432 0.6800 0.0906 0.106 Uiso 1 1 calc R . .
C16 C 0.5754(7) 0.6250(4) 0.0982(3) 0.0811(13) Uani 1 1 d . . .
H16 H 0.5937 0.6318 0.0375 0.097 Uiso 1 1 calc R . .
C14 C 0.4029(6) 0.6462(4) 0.2191(4) 0.0834(13) Uani 1 1 d . . .
H14 H 0.3033 0.6677 0.2408 0.100 Uiso 1 1 calc R . .
C19 C 0.8602(5) 0.8442(4) 0.8625(2) 0.0556(10) Uani 1 1 d . . .
C20 C 0.9314(5) 0.9740(4) 0.8656(2) 0.0563(10) Uani 1 1 d . . .
C21 C 1.1222(6) 1.0446(4) 0.8974(2) 0.0720(11) Uani 1 1 d . . .
H21 H 1.1654 1.1325 0.9000 0.086 Uiso 1 1 calc R . .
C18 C 0.6514(6) 0.7621(4) 0.8322(3) 0.0638(11) Uani 1 1 d . . .
C24 C 0.9898(6) 0.7838(4) 0.8908(2) 0.0722(11) Uani 1 1 d . . .
H24 H 0.9465 0.6960 0.8895 0.087 Uiso 1 1 calc R . .
C23 C 1.1838(6) 0.8532(6) 0.9210(3) 0.0844(13) Uani 1 1 d . . .
H23 H 1.2707 0.8119 0.9385 0.101 Uiso 1 1 calc R . .
C22 C 1.2465(6) 0.9825(6) 0.9251(3) 0.0852(13) Uani 1 1 d . . .
H22 H 1.3757 1.0289 0.9470 0.102 Uiso 1 1 calc R . .
N2 N 1.0064(5) 0.6857(3) 0.61082(18) 0.0586(9) Uani 1 1 d . . .
N1 N 0.4036(4) 0.7415(3) 0.46941(18) 0.0610(8) Uani 1 1 d . . .
N4 N 0.8022(6) 1.0435(4) 0.8353(2) 0.0727(10) Uani 1 1 d . . .
N3 N 0.8505(5) 0.5494(4) 0.1225(3) 0.0912(12) Uani 1 1 d . . .
O1 O 0.2708(3) 0.7980(2) 0.43929(17) 0.0785(8) Uani 1 1 d . . .
H1A H 0.1729 0.7439 0.4110 0.118 Uiso 1 1 calc R . .
O5 O 0.7295(3) 0.4167(3) 0.33270(16) 0.0716(8) Uani 1 1 d . . .
O4 O 0.9565(3) 0.6067(2) 0.35730(18) 0.0892(9) Uani 1 1 d . . .
O7 O 0.6117(3) 0.7336(3) 0.74358(17) 0.0831(8) Uani 1 1 d . . .
H7A H 0.5002 0.6844 0.7297 0.125 Uiso 1 1 calc R . .
O6 O 0.5410(4) 0.7217(3) 0.88536(19) 0.0939(9) Uani 1 1 d . . .
O8 O 0.6319(4) 0.9877(3) 0.8196(2) 0.1239(13) Uani 1 1 d . . .
O2 O 0.9356(4) 0.4923(3) 0.1666(2) 0.1054(11) Uani 1 1 d . . .
O9 O 0.8726(5) 1.1540(4) 0.8267(3) 0.1305(13) Uani 1 1 d . . .
O3 O 0.8901(6) 0.5818(5) 0.0480(3) 0.183(2) Uani 1 1 d . . .
H2A H 1.102(5) 0.646(3) 0.632(2) 0.080(13) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C2 C3 1.368(4) . ?
C2 C9 1.425(4) . ?
C2 C1 1.465(4) . ?
C9 C8 1.402(4) . ?
C9 C10 1.410(4) . ?
C8 C7 1.367(4) . ?
C1 N1 1.278(4) . ?
C5 C6 1.357(4) . ?
C5 C10 1.404(4) . ?
C10 N2 1.375(4) . ?
C4 N2 1.322(4) . ?
C4 C3 1.378(4) . ?
C7 C6 1.394(4) . ?
C12 C13 1.380(4) . ?
C12 C17 1.388(4) . ?
C12 C11 1.501(4) . ?
C17 C16 1.390(5) . ?
C17 N3 1.446(5) . ?
C11 O4 1.239(4) . ?
C11 O5 1.270(4) . ?
C13 C14 1.370(5) . ?
C15 C14 1.358(5) . ?
C15 C16 1.366(5) . ?
C19 C20 1.374(4) . ?
C19 C24 1.386(4) . ?
C19 C18 1.510(5) . ?
C20 C21 1.377(4) . ?
C20 N4 1.469(5) . ?
C21 C22 1.366(5) . ?
C18 O6 1.205(4) . ?
C18 O7 1.303(4) . ?
C24 C23 1.390(5) . ?
C23 C22 1.368(5) . ?
N1 O1 1.381(3) . ?
N4 O8 1.193(4) . ?
N4 O9 1.202(3) . ?
N3 O2 1.207(4) . ?
N3 O3 1.225(4) . ?

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
C3 C2 C9 118.5(3) . . ?
C3 C2 C1 119.8(3) . . ?
C9 C2 C1 121.7(3) . . ?
C8 C9 C10 117.6(3) . . ?
C8 C9 C2 124.1(3) . . ?
C10 C9 C2 118.3(3) . . ?
C7 C8 C9 120.2(3) . . ?
N1 C1 C2 118.4(3) . . ?
C6 C5 C10 118.6(4) . . ?
N2 C10 C5 119.1(4) . . ?
N2 C10 C9 119.4(3) . . ?
C5 C10 C9 121.6(4) . . ?
N2 C4 C3 120.4(4) . . ?
C2 C3 C4 121.4(3) . . ?
C8 C7 C6 121.2(4) . . ?
C5 C6 C7 120.8(3) . . ?
C13 C12 C17 116.4(3) . . ?
C13 C12 C11 119.0(4) . . ?
C17 C12 C11 124.6(4) . . ?
C12 C17 C16 121.6(4) . . ?
C12 C17 N3 119.2(4) . . ?
C16 C17 N3 119.1(4) . . ?
O4 C11 O5 124.1(3) . . ?
O4 C11 C12 119.8(4) . . ?
O5 C11 C12 115.8(3) . . ?
C14 C13 C12 122.2(4) . . ?
C14 C15 C16 120.2(4) . . ?
C15 C16 C17 119.3(4) . . ?
C15 C14 C13 120.1(4) . . ?
C20 C19 C24 117.5(3) . . ?
C20 C19 C18 125.3(3) . . ?
C24 C19 C18 117.2(4) . . ?
C19 C20 C21 122.8(4) . . ?
C19 C20 N4 120.2(3) . . ?
C21 C20 N4 117.1(4) . . ?
C22 C21 C20 118.4(4) . . ?
O6 C18 O7 125.0(4) . . ?
O6 C18 C19 122.9(4) . . ?
O7 C18 C19 111.9(4) . . ?
C19 C24 C23 120.6(4) . . ?
C22 C23 C24 119.7(4) . . ?
C21 C22 C23 121.0(4) . . ?
C4 N2 C10 122.0(4) . . ?
C1 N1 O1 111.5(3) . . ?
O8 N4 O9 122.8(4) . . ?
O8 N4 C20 118.6(4) . . ?
O9 N4 C20 118.6(4) . . ?
O2 N3 O3 122.3(5) . . ?
O2 N3 C17 120.6(4) . . ?
O3 N3 C17 117.1(5) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.041
####################################################################### 
# 
# 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_11
_database_code_depnum_ccdc_archive 'CCDC 1468838'
_audit_update_record             
;
2016-10-13 deposited with the CCDC.
2016-11-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H9 N2 O, C7 H4 N O4'
_chemical_formula_sum            'C17 H13 N3 O5'
_chemical_formula_weight         339.30

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'
_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                   14.4119(6)
_cell_length_b                   7.3071(3)
_cell_length_c                   15.2855(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.646(3)
_cell_angle_gamma                90.00
_cell_volume                     1542.25(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3412
_cell_measurement_theta_min      2.75
_cell_measurement_theta_max      21.58

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             704
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.968
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_process_details   multi-scan

_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 and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19095
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_av_sigmaI/netI    0.0316
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.47
_diffrn_reflns_theta_max         25.25
_reflns_number_total             2776
_reflns_number_gt                1884
_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)+(0.0800P)²+0.0200P] 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         2776
_refine_ls_number_parameters     231
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0707
_refine_ls_R_factor_gt           0.0438
_refine_ls_wR_factor_ref         0.1350
_refine_ls_wR_factor_gt          0.1166
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.061
_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
C3 C 0.37049(15) 0.6074(3) 0.97166(13) 0.0472(5) Uani 1 1 d . . .
H3 H 0.4329 0.6501 0.9784 0.057 Uiso 1 1 calc R . .
C2 C 0.30947(14) 0.5743(2) 0.88571(13) 0.0406(5) Uani 1 1 d . . .
C9 C 0.21485(13) 0.5063(3) 0.87840(13) 0.0406(5) Uani 1 1 d . . .
C5 C 0.09697(15) 0.4043(3) 0.95660(15) 0.0540(6) Uani 1 1 d . . .
H5 H 0.0803 0.3848 1.0103 0.065 Uiso 1 1 calc R . .
C10 C 0.18839(13) 0.4768(3) 0.95953(13) 0.0423(5) Uani 1 1 d . . .
C1 C 0.34156(15) 0.6083(3) 0.80443(14) 0.0492(5) Uani 1 1 d . . .
H1 H 0.2967 0.6179 0.7472 0.059 Uiso 1 1 calc R . .
C4 C 0.33940(15) 0.5774(3) 1.04813(14) 0.0516(6) Uani 1 1 d . . .
H4 H 0.3818 0.6013 1.1055 0.062 Uiso 1 1 calc R . .
C8 C 0.14571(14) 0.4613(3) 0.79463(14) 0.0535(6) Uani 1 1 d . . .
H8 H 0.1606 0.4804 0.7400 0.064 Uiso 1 1 calc R . .
C7 C 0.05778(15) 0.3902(3) 0.79298(16) 0.0639(7) Uani 1 1 d . . .
H7 H 0.0137 0.3596 0.7374 0.077 Uiso 1 1 calc R . .
C6 C 0.03325(15) 0.3629(3) 0.87422(17) 0.0631(7) Uani 1 1 d . . .
H6 H -0.0274 0.3159 0.8720 0.076 Uiso 1 1 calc R . .
C12 C 0.29516(13) 0.4327(3) 0.35507(12) 0.0401(5) Uani 1 1 d . . .
C14 C 0.22103(13) 0.5026(3) 0.47212(13) 0.0421(5) Uani 1 1 d . . .
C11 C 0.29292(14) 0.4215(3) 0.25672(14) 0.0458(5) Uani 1 1 d . . .
C13 C 0.21623(13) 0.4984(2) 0.38043(13) 0.0417(5) Uani 1 1 d . . .
H13 H 0.1611 0.5390 0.3365 0.050 Uiso 1 1 calc R . .
C17 C 0.37725(14) 0.3757(3) 0.42259(14) 0.0488(5) Uani 1 1 d . . .
H17 H 0.4307 0.3328 0.4062 0.059 Uiso 1 1 calc R . .
C15 C 0.30205(15) 0.4443(3) 0.53910(14) 0.0506(5) Uani 1 1 d . . .
H15 H 0.3035 0.4472 0.6003 0.061 Uiso 1 1 calc R . .
C16 C 0.38030(15) 0.3821(3) 0.51384(14) 0.0530(6) Uani 1 1 d . . .
H16 H 0.4357 0.3440 0.5582 0.064 Uiso 1 1 calc R . .
N2 N 0.25180(12) 0.5162(2) 1.04248(11) 0.0480(4) Uani 1 1 d D . .
N3 N 0.13809(13) 0.5743(2) 0.49924(13) 0.0542(5) Uani 1 1 d . . .
N1 N 0.43232(13) 0.6246(2) 0.81350(12) 0.0557(5) Uani 1 1 d . . .
O4 O 0.21992(10) 0.4959(2) 0.19931(9) 0.0598(4) Uani 1 1 d . . .
O1 O 0.44967(11) 0.6587(3) 0.73068(10) 0.0710(5) Uani 1 1 d . . .
H1A H 0.5082 0.6659 0.7381 0.106 Uiso 1 1 calc R . .
O5 O 0.35823(11) 0.3433(2) 0.23429(10) 0.0676(5) Uani 1 1 d . . .
O3 O 0.06729(12) 0.6282(2) 0.44011(11) 0.0719(5) Uani 1 1 d . . .
O2 O 0.14421(13) 0.5798(3) 0.58059(12) 0.0884(6) Uani 1 1 d . . .
H2A H 0.236(2) 0.501(4) 1.1000(11) 0.121(11) Uiso 1 1 d D . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C3 C2 1.377(3) . ?
C3 C4 1.384(3) . ?
C2 C9 1.425(3) . ?
C2 C1 1.466(3) . ?
C9 C10 1.414(3) . ?
C9 C8 1.418(3) . ?
C5 C6 1.363(3) . ?
C5 C10 1.409(3) . ?
C10 N2 1.365(2) . ?
C1 N1 1.281(3) . ?
C4 N2 1.319(2) . ?
C8 C7 1.363(3) . ?
C7 C6 1.399(3) . ?
C12 C13 1.388(3) . ?
C12 C17 1.392(3) . ?
C12 C11 1.497(3) . ?
C14 C15 1.381(3) . ?
C14 C13 1.384(3) . ?
C14 N3 1.469(3) . ?
C11 O5 1.231(2) . ?
C11 O4 1.282(2) . ?
C17 C16 1.384(3) . ?
C15 C16 1.370(3) . ?
N3 O3 1.219(2) . ?
N3 O2 1.222(2) . ?
N1 O1 1.381(2) . ?

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
C2 C3 C4 120.35(19) . . ?
C3 C2 C9 118.11(18) . . ?
C3 C2 C1 120.57(18) . . ?
C9 C2 C1 121.31(17) . . ?
C10 C9 C8 117.40(18) . . ?
C10 C9 C2 118.46(17) . . ?
C8 C9 C2 124.12(18) . . ?
C6 C5 C10 119.3(2) . . ?
N2 C10 C5 118.69(18) . . ?
N2 C10 C9 120.37(17) . . ?
C5 C10 C9 120.93(18) . . ?
N1 C1 C2 118.98(18) . . ?
N2 C4 C3 122.27(18) . . ?
C7 C8 C9 121.0(2) . . ?
C8 C7 C6 120.5(2) . . ?
C5 C6 C7 120.9(2) . . ?
C13 C12 C17 119.12(18) . . ?
C13 C12 C11 121.04(17) . . ?
C17 C12 C11 119.84(18) . . ?
C15 C14 C13 122.03(18) . . ?
C15 C14 N3 118.95(18) . . ?
C13 C14 N3 119.01(17) . . ?
O5 C11 O4 123.33(19) . . ?
O5 C11 C12 120.46(18) . . ?
O4 C11 C12 116.21(17) . . ?
C14 C13 C12 118.89(17) . . ?
C16 C17 C12 120.80(19) . . ?
C16 C15 C14 118.87(19) . . ?
C15 C16 C17 120.28(18) . . ?
C4 N2 C10 120.40(17) . . ?
O3 N3 O2 123.04(19) . . ?
O3 N3 C14 118.81(18) . . ?
O2 N3 C14 118.13(18) . . ?
C1 N1 O1 111.40(16) . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.039
####################################################################### 
# 
# 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_fdg
_database_code_depnum_ccdc_archive 'CCDC 1468839'
_audit_update_record             
;
2016-10-13 deposited with the CCDC.
2016-11-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H9 N2 O, C7 H4 N O4'
_chemical_formula_sum            'C17 H13 N3 O5'
_chemical_formula_weight         339.30

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

_cell_length_a                   6.5509(4)
_cell_length_b                   9.5558(7)
_cell_length_c                   24.5384(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.662(4)
_cell_angle_gamma                90.00
_cell_volume                     1535.44(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2543
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      20.96

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             704
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.969
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_process_details   multi-scan

_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 and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17556
_diffrn_reflns_av_R_equivalents  0.0534
_diffrn_reflns_av_sigmaI/netI    0.0848
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.66
_diffrn_reflns_theta_max         25.25
_reflns_number_total             2697
_reflns_number_gt                1652
_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)+(0.0800P)²+0.0200P] 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         2697
_refine_ls_number_parameters     231
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0960
_refine_ls_R_factor_gt           0.0553
_refine_ls_wR_factor_ref         0.1713
_refine_ls_wR_factor_gt          0.1441
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.016
_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
C12 C 0.6022(3) 0.4113(2) 0.16112(9) 0.0466(6) Uani 1 1 d . . .
C15 C 0.2546(4) 0.4205(3) 0.22121(10) 0.0538(7) Uani 1 1 d . . .
C2 C 0.5672(4) 0.2137(2) 0.01929(10) 0.0468(6) Uani 1 1 d . . .
C9 C 0.5166(3) 0.1194(2) 0.06205(9) 0.0453(6) Uani 1 1 d . . .
C10 C 0.3309(4) 0.1412(2) 0.08882(9) 0.0474(6) Uani 1 1 d . . .
C3 C 0.4361(4) 0.3226(3) 0.00701(10) 0.0530(7) Uani 1 1 d . . .
H3 H 0.4647 0.3838 -0.0212 0.064 Uiso 1 1 calc R . .
C1 C 0.7524(4) 0.1943(3) -0.01193(10) 0.0553(7) Uani 1 1 d . . .
H1 H 0.8182 0.1081 -0.0118 0.066 Uiso 1 1 calc R . .
C11 C 0.7911(4) 0.4061(3) 0.12762(10) 0.0541(7) Uani 1 1 d . . .
C13 C 0.5594(4) 0.3037(3) 0.19712(10) 0.0533(7) Uani 1 1 d . . .
H13 H 0.6487 0.2285 0.2010 0.064 Uiso 1 1 calc R . .
C5 C 0.2695(4) 0.0493(3) 0.13011(10) 0.0601(7) Uani 1 1 d . . .
H5 H 0.1451 0.0627 0.1467 0.072 Uiso 1 1 calc R . .
C16 C 0.2936(4) 0.5288(3) 0.18604(10) 0.0601(7) Uani 1 1 d . . .
H16 H 0.2043 0.6041 0.1825 0.072 Uiso 1 1 calc R . .
C14 C 0.3841(4) 0.3082(3) 0.22725(10) 0.0579(7) Uani 1 1 d . . .
H14 H 0.3544 0.2362 0.2512 0.069 Uiso 1 1 calc R . .
C4 C 0.2609(4) 0.3408(3) 0.03686(10) 0.0572(7) Uani 1 1 d . . .
H4 H 0.1770 0.4171 0.0290 0.069 Uiso 1 1 calc R . .
C17 C 0.4682(4) 0.5231(3) 0.15610(10) 0.0576(7) Uani 1 1 d . . .
H17 H 0.4965 0.5954 0.1321 0.069 Uiso 1 1 calc R . .
C8 C 0.6402(4) 0.0058(3) 0.08000(10) 0.0578(7) Uani 1 1 d . . .
H8 H 0.7647 -0.0102 0.0638 0.069 Uiso 1 1 calc R . .
C7 C 0.5789(4) -0.0802(3) 0.12058(11) 0.0649(8) Uani 1 1 d . . .
H7 H 0.6621 -0.1542 0.1318 0.078 Uiso 1 1 calc R . .
C6 C 0.3920(5) -0.0588(3) 0.14565(11) 0.0658(8) Uani 1 1 d . . .
H6 H 0.3518 -0.1190 0.1731 0.079 Uiso 1 1 calc R . .
N2 N 0.2092(3) 0.2542(2) 0.07573(8) 0.0536(6) Uani 1 1 d D . .
N1 N 0.8230(3) 0.2955(2) -0.03923(9) 0.0587(6) Uani 1 1 d . . .
N3 N 0.0682(4) 0.4264(3) 0.25314(9) 0.0680(7) Uani 1 1 d . . .
O2 O 0.8990(3) 0.29467(19) 0.13431(7) 0.0664(6) Uani 1 1 d . . .
O3 O 0.8306(3) 0.5018(2) 0.09636(8) 0.0768(6) Uani 1 1 d . . .
O1 O 0.9938(3) 0.25578(19) -0.06731(8) 0.0721(6) Uani 1 1 d . . .
H1A H 1.0443 0.3247 -0.0816 0.108 Uiso 1 1 calc R . .
O5 O -0.0504(3) 0.5224(3) 0.24561(9) 0.1032(8) Uani 1 1 d . . .
O4 O 0.0384(3) 0.3323(3) 0.28564(10) 0.0987(8) Uani 1 1 d . . .
H2 H 0.094(3) 0.266(3) 0.0978(10) 0.099(11) Uiso 1 1 d D . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C12 C17 1.386(3) . ?
C12 C13 1.389(3) . ?
C12 C11 1.506(3) . ?
C15 C14 1.373(3) . ?
C15 C16 1.376(3) . ?
C15 N3 1.471(3) . ?
C2 C3 1.377(3) . ?
C2 C9 1.429(3) . ?
C2 C1 1.465(3) . ?
C9 C10 1.414(3) . ?
C9 C8 1.416(3) . ?
C10 N2 1.375(3) . ?
C10 C5 1.409(3) . ?
C3 C4 1.391(3) . ?
C1 N1 1.271(3) . ?
C11 O3 1.226(3) . ?
C11 O2 1.286(3) . ?
C13 C14 1.384(3) . ?
C5 C6 1.356(4) . ?
C16 C17 1.378(3) . ?
C4 N2 1.314(3) . ?
C8 C7 1.361(3) . ?
C7 C6 1.401(4) . ?
N1 O1 1.384(2) . ?
N3 O5 1.213(3) . ?
N3 O4 1.221(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
C17 C12 C13 119.2(2) . . ?
C17 C12 C11 120.4(2) . . ?
C13 C12 C11 120.5(2) . . ?
C14 C15 C16 122.0(2) . . ?
C14 C15 N3 119.5(2) . . ?
C16 C15 N3 118.5(2) . . ?
C3 C2 C9 118.7(2) . . ?
C3 C2 C1 120.1(2) . . ?
C9 C2 C1 121.2(2) . . ?
C10 C9 C8 117.4(2) . . ?
C10 C9 C2 117.9(2) . . ?
C8 C9 C2 124.7(2) . . ?
N2 C10 C5 118.8(2) . . ?
N2 C10 C9 120.5(2) . . ?
C5 C10 C9 120.6(2) . . ?
C2 C3 C4 119.9(2) . . ?
N1 C1 C2 119.9(2) . . ?
O3 C11 O2 124.9(2) . . ?
O3 C11 C12 120.6(2) . . ?
O2 C11 C12 114.5(2) . . ?
C14 C13 C12 120.2(2) . . ?
C6 C5 C10 119.9(2) . . ?
C15 C16 C17 118.5(2) . . ?
C15 C14 C13 119.1(2) . . ?
N2 C4 C3 122.5(2) . . ?
C16 C17 C12 121.1(2) . . ?
C7 C8 C9 120.8(2) . . ?
C8 C7 C6 120.9(2) . . ?
C5 C6 C7 120.4(2) . . ?
C4 N2 C10 120.3(2) . . ?
C1 N1 O1 111.4(2) . . ?
O5 N3 O4 122.8(3) . . ?
O5 N3 C15 119.1(3) . . ?
O4 N3 C15 118.1(3) . . ?

_diffrn_measured_fraction_theta_max 0.970
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.970
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.048
####################################################################### 
# 
# 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_exp_2508
_database_code_depnum_ccdc_archive 'CCDC 1481864'
_audit_update_record             
;
2016-10-13 deposited with the CCDC.
2016-11-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H9 N2 O, C7 H5 O3'
_chemical_formula_sum            'C17 H14 N2 O4'
_chemical_formula_weight         310.30

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'
F F 0.0171 0.0103 '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'
_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                   9.0241(15)
_cell_length_b                   11.982(2)
_cell_length_c                   14.549(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.874(19)
_cell_angle_gamma                90.00
_cell_volume                     1497.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1052
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      20.30

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1252
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.972
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_process_details   multi-scan

_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 and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3384
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_av_sigmaI/netI    0.0597
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.92
_diffrn_reflns_theta_max         25.24
_reflns_number_total             2690
_reflns_number_gt                1114
_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)+(0.0100P)²+5.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2690
_refine_ls_number_parameters     214
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1722
_refine_ls_R_factor_gt           0.0928
_refine_ls_wR_factor_ref         0.1945
_refine_ls_wR_factor_gt          0.1547
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_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
O3 O 0.4949(6) 0.3538(4) 0.3721(4) 0.0760(15) Uani 1 1 d . . .
O2 O 0.3522(5) 0.5045(4) 0.3173(4) 0.0739(14) Uani 1 1 d . . .
C9 C 0.7431(7) 0.7797(5) 0.4809(4) 0.0453(15) Uani 1 1 d . . .
C13 C 0.2625(10) 0.2075(6) 0.2744(5) 0.080(3) Uani 1 1 d . . .
H13 H 0.3557 0.1752 0.3110 0.096 Uiso 1 1 calc R . .
N2 N 0.6049(8) 0.6082(5) 0.4255(5) 0.0617(15) Uani 1 1 d D . .
C2 C 0.8743(8) 0.7143(5) 0.5321(5) 0.0545(17) Uani 1 1 d . . .
O1 O 1.2751(6) 0.7733(5) 0.6439(5) 0.1001(19) Uani 1 1 d . . .
H1 H 1.3544 0.7397 0.6443 0.150 Uiso 1 1 calc R . .
C12 C 0.2400(7) 0.3270(5) 0.2650(4) 0.0479(15) Uani 1 1 d . . .
C10 C 0.6082(8) 0.7233(5) 0.4267(5) 0.0538(17) Uani 1 1 d . . .
C3 C 0.8633(8) 0.5983(5) 0.5281(5) 0.0592(18) Uani 1 1 d . . .
H3 H 0.9482 0.5548 0.5613 0.071 Uiso 1 1 calc R . .
C17 C 0.1022(9) 0.3728(6) 0.2081(5) 0.0613(18) Uani 1 1 d . . .
C11 C 0.3720(8) 0.3978(6) 0.3209(5) 0.0583(18) Uani 1 1 d . . .
C7 C 0.6133(9) 0.9527(6) 0.4259(5) 0.073(2) Uani 1 1 d . . .
H7 H 0.6134 1.0303 0.4248 0.088 Uiso 1 1 calc R . .
N1 N 1.1463(7) 0.7106(5) 0.5958(4) 0.0728(17) Uani 1 1 d . . .
C8 C 0.7422(9) 0.8971(5) 0.4784(5) 0.0625(19) Uani 1 1 d . . .
H8 H 0.8304 0.9367 0.5128 0.075 Uiso 1 1 calc R . .
O4 O 0.0833(7) 0.4809(5) 0.1946(5) 0.112(2) Uani 1 1 d . . .
H4 H 0.1581 0.5138 0.2311 0.167 Uiso 1 1 calc R . .
C4 C 0.7271(9) 0.5483(6) 0.4751(5) 0.0636(19) Uani 1 1 d . . .
H4A H 0.7203 0.4708 0.4739 0.076 Uiso 1 1 calc R . .
C5 C 0.4735(8) 0.7816(6) 0.3732(5) 0.0645(19) Uani 1 1 d . . .
H5 H 0.3835 0.7438 0.3389 0.077 Uiso 1 1 calc R . .
C14 C 0.1329(11) 0.1447(7) 0.2239(6) 0.082(2) Uani 1 1 d . . .
H14 H 0.1405 0.0674 0.2278 0.098 Uiso 1 1 calc R . .
C6 C 0.4797(9) 0.8943(7) 0.3734(5) 0.074(2) Uani 1 1 d . . .
H6 H 0.3928 0.9343 0.3376 0.089 Uiso 1 1 calc R . .
C16 C -0.0245(8) 0.3049(7) 0.1583(5) 0.076(2) Uani 1 1 d . . .
H16 H -0.1173 0.3361 0.1200 0.091 Uiso 1 1 calc R . .
C1 C 1.0214(8) 0.7673(6) 0.5835(5) 0.066(2) Uani 1 1 d . . .
H1A H 1.0247 0.8399 0.6067 0.080 Uiso 1 1 calc R . .
C15 C -0.0069(10) 0.1912(7) 0.1682(6) 0.082(2) Uani 1 1 d . . .
H15 H -0.0897 0.1447 0.1372 0.098 Uiso 1 1 calc R . .
H2A H 0.519(5) 0.582(6) 0.386(4) 0.10(3) Uiso 1 1 d D . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O3 C11 1.247(8) . ?
O2 C11 1.290(7) . ?
C9 C10 1.404(8) . ?
C9 C8 1.408(8) . ?
C9 C2 1.425(8) . ?
C13 C14 1.395(10) . ?
C13 C12 1.447(9) . ?
N2 C4 1.328(9) . ?
N2 C10 1.379(8) . ?
C2 C3 1.394(8) . ?
C2 C1 1.455(9) . ?
O1 N1 1.381(7) . ?
C12 C17 1.379(9) . ?
C12 C11 1.485(9) . ?
C10 C5 1.412(9) . ?
C3 C4 1.372(9) . ?
C17 O4 1.314(8) . ?
C17 C16 1.409(9) . ?
C7 C8 1.354(9) . ?
C7 C6 1.400(10) . ?
N1 C1 1.281(8) . ?
C5 C6 1.351(9) . ?
C14 C15 1.390(10) . ?
C16 C15 1.374(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 C9 C8 118.0(6) . . ?
C10 C9 C2 117.8(5) . . ?
C8 C9 C2 124.1(6) . . ?
C14 C13 C12 114.4(8) . . ?
C4 N2 C10 121.5(7) . . ?
C3 C2 C9 119.3(6) . . ?
C3 C2 C1 120.0(6) . . ?
C9 C2 C1 120.6(6) . . ?
C17 C12 C13 121.7(6) . . ?
C17 C12 C11 121.7(6) . . ?
C13 C12 C11 116.6(6) . . ?
N2 C10 C9 120.0(6) . . ?
N2 C10 C5 118.5(7) . . ?
C9 C10 C5 121.5(6) . . ?
C4 C3 C2 119.9(7) . . ?
O4 C17 C12 122.3(7) . . ?
O4 C17 C16 116.4(7) . . ?
C12 C17 C16 121.3(7) . . ?
O3 C11 O2 122.0(7) . . ?
O3 C11 C12 120.1(6) . . ?
O2 C11 C12 117.8(6) . . ?
C8 C7 C6 120.6(7) . . ?
C1 N1 O1 110.5(6) . . ?
C7 C8 C9 120.2(7) . . ?
N2 C4 C3 121.4(7) . . ?
C6 C5 C10 117.7(7) . . ?
C15 C14 C13 123.8(8) . . ?
C5 C6 C7 121.9(7) . . ?
C15 C16 C17 118.0(8) . . ?
N1 C1 C2 117.7(6) . . ?
C16 C15 C14 120.9(7) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.578
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.053
####################################################################### 
# 
# 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_11
_database_code_depnum_ccdc_archive 'CCDC 1481865'
_audit_update_record             
;
2016-10-13 deposited with the CCDC.
2016-11-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H8 N2 O, C8 H8 O2'
_chemical_formula_sum            'C18 H16 N2 O3'
_chemical_formula_weight         308.33

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'
_space_group_name_Hall           '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   3.9318(5)
_cell_length_b                   11.7049(15)
_cell_length_c                   16.914(2)
_cell_angle_alpha                99.084(8)
_cell_angle_beta                 94.248(8)
_cell_angle_gamma                94.176(8)
_cell_volume                     763.69(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    486
_cell_measurement_theta_min      2.78
_cell_measurement_theta_max      19.22

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             324
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.974
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_process_details   multi-scan

_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 and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5169
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_av_sigmaI/netI    0.0910
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.22
_diffrn_reflns_theta_max         25.24
_reflns_number_total             2760
_reflns_number_gt                1250
_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)+(0.0500P)²+0.3000P] 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         2760
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1602
_refine_ls_R_factor_gt           0.0555
_refine_ls_wR_factor_ref         0.1705
_refine_ls_wR_factor_gt          0.1151
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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
C9 C 0.4578(12) 0.2268(4) 0.1124(3) 0.0580(14) Uani 1 1 d . . .
C2 C 0.3137(12) 0.2925(5) 0.0559(3) 0.0612(14) Uani 1 1 d . . .
C3 C 0.3509(13) 0.4107(5) 0.0754(3) 0.0704(16) Uani 1 1 d . . .
H3 H 0.2591 0.4562 0.0402 0.084 Uiso 1 1 calc R . .
C10 C 0.6302(13) 0.2876(5) 0.1848(3) 0.0610(14) Uani 1 1 d . . .
C1 C 0.1317(13) 0.2339(4) -0.0209(3) 0.0725(16) Uani 1 1 d . . .
H1 H 0.0516 0.1560 -0.0272 0.087 Uiso 1 1 calc R . .
C5 C 0.7792(13) 0.2266(5) 0.2420(3) 0.0732(16) Uani 1 1 d . . .
H5 H 0.8940 0.2674 0.2892 0.088 Uiso 1 1 calc R . .
C8 C 0.4429(13) 0.1032(5) 0.1009(3) 0.0699(15) Uani 1 1 d . . .
H8 H 0.3330 0.0603 0.0538 0.084 Uiso 1 1 calc R . .
C4 C 0.5274(14) 0.4633(5) 0.1485(3) 0.0755(17) Uani 1 1 d . . .
H4 H 0.5505 0.5440 0.1598 0.091 Uiso 1 1 calc R . .
C7 C 0.5875(15) 0.0466(4) 0.1580(3) 0.0834(18) Uani 1 1 d . . .
H7 H 0.5724 -0.0341 0.1495 0.100 Uiso 1 1 calc R . .
C6 C 0.7565(14) 0.1083(6) 0.2286(3) 0.0811(18) Uani 1 1 d . . .
H6 H 0.8545 0.0688 0.2668 0.097 Uiso 1 1 calc R . .
C17 C 0.3148(12) 0.6861(4) 0.4082(3) 0.0557(14) Uani 1 1 d . . .
C12 C 0.4706(13) 0.7990(4) 0.4143(3) 0.0650(15) Uani 1 1 d . . .
C18 C 0.1298(13) 0.6234(5) 0.3318(3) 0.0664(16) Uani 1 1 d . . .
C16 C 0.3268(12) 0.6306(4) 0.4742(3) 0.0641(15) Uani 1 1 d . . .
H16 H 0.2242 0.5553 0.4693 0.077 Uiso 1 1 calc R . .
C13 C 0.6349(12) 0.8511(5) 0.4892(4) 0.0762(17) Uani 1 1 d . . .
H13 H 0.7429 0.9257 0.4950 0.091 Uiso 1 1 calc R . .
C15 C 0.4870(14) 0.6837(5) 0.5472(3) 0.0788(17) Uani 1 1 d . . .
H15 H 0.4924 0.6455 0.5915 0.095 Uiso 1 1 calc R . .
C14 C 0.6387(14) 0.7946(5) 0.5531(4) 0.0851(19) Uani 1 1 d . . .
H14 H 0.7467 0.8317 0.6022 0.102 Uiso 1 1 calc R . .
C11 C 0.4761(13) 0.8675(4) 0.3462(3) 0.0929(19) Uani 1 1 d . . .
H11A H 0.5778 0.8247 0.3021 0.139 Uiso 1 1 calc R . .
H11B H 0.6077 0.9406 0.3639 0.139 Uiso 1 1 calc R . .
H11C H 0.2463 0.8809 0.3291 0.139 Uiso 1 1 calc R . .
O2 O 0.0935(10) 0.6634(3) 0.2700(2) 0.0965(14) Uani 1 1 d . . .
O3 O 0.0112(10) 0.5177(3) 0.33587(19) 0.0875(12) Uani 1 1 d . . .
H3A H -0.1080 0.4904 0.2944 0.131 Uiso 1 1 calc R . .
O1 O -0.0866(11) 0.2193(3) -0.1452(2) 0.1009(14) Uani 1 1 d . . .
H1A H -0.1087 0.2559 -0.1826 0.151 Uiso 1 1 calc R . .
N2 N 0.6624(11) 0.4065(4) 0.2022(2) 0.0716(13) Uani 1 1 d . . .
N1 N 0.0850(11) 0.2911(4) -0.0786(3) 0.0806(14) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C9 C10 1.414(6) . ?
C9 C8 1.425(6) . ?
C9 C2 1.428(6) . ?
C2 C3 1.365(6) . ?
C2 C1 1.476(6) . ?
C3 C4 1.400(6) . ?
C10 N2 1.370(5) . ?
C10 C5 1.408(6) . ?
C1 N1 1.277(5) . ?
C5 C6 1.362(6) . ?
C8 C7 1.368(6) . ?
C4 N2 1.311(5) . ?
C7 C6 1.388(6) . ?
C17 C16 1.378(5) . ?
C17 C12 1.401(6) . ?
C17 C18 1.490(6) . ?
C12 C13 1.405(6) . ?
C12 C11 1.504(6) . ?
C18 O2 1.214(5) . ?
C18 O3 1.304(5) . ?
C16 C15 1.377(6) . ?
C13 C14 1.353(6) . ?
C15 C14 1.374(6) . ?
O1 N1 1.392(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 C9 C8 117.0(5) . . ?
C10 C9 C2 118.3(5) . . ?
C8 C9 C2 124.7(5) . . ?
C3 C2 C9 117.8(5) . . ?
C3 C2 C1 121.5(5) . . ?
C9 C2 C1 120.8(5) . . ?
C2 C3 C4 119.9(5) . . ?
N2 C10 C5 117.4(5) . . ?
N2 C10 C9 122.2(5) . . ?
C5 C10 C9 120.3(5) . . ?
N1 C1 C2 119.4(5) . . ?
C6 C5 C10 120.5(5) . . ?
C7 C8 C9 121.1(5) . . ?
N2 C4 C3 124.4(5) . . ?
C8 C7 C6 120.7(5) . . ?
C5 C6 C7 120.2(5) . . ?
C16 C17 C12 119.9(5) . . ?
C16 C17 C18 118.2(5) . . ?
C12 C17 C18 121.9(5) . . ?
C17 C12 C13 117.5(5) . . ?
C17 C12 C11 124.5(5) . . ?
C13 C12 C11 118.0(5) . . ?
O2 C18 O3 121.5(5) . . ?
O2 C18 C17 124.8(5) . . ?
O3 C18 C17 113.8(5) . . ?
C15 C16 C17 121.6(5) . . ?
C14 C13 C12 121.1(5) . . ?
C14 C15 C16 118.3(5) . . ?
C13 C14 C15 121.6(5) . . ?
C4 N2 C10 117.5(5) . . ?
C1 N1 O1 110.0(4) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.048
####################################################################### 
# 
# 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_1213
_database_code_depnum_ccdc_archive 'CCDC 1481866'
_audit_update_record             
;
2016-10-13 deposited with the CCDC.
2016-11-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C10 H9 N2 O), 2(C7 H5 O4), H2 O'
_chemical_formula_sum            'C34 H30 N4 O11'
_chemical_formula_weight         670.62

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_space_group_name_Hall           '-C 2yc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   16.7216(18)
_cell_length_b                   10.9118(11)
_cell_length_c                   18.807(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 113.093(6)
_cell_angle_gamma                90.00
_cell_volume                     3156.7(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2768
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      23.00

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1400
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.970
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_process_details   multi-scan

_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 and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18990
_diffrn_reflns_av_R_equivalents  0.0586
_diffrn_reflns_av_sigmaI/netI    0.0692
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.29
_diffrn_reflns_theta_max         25.05
_reflns_number_total             2739
_reflns_number_gt                1679
_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)+(0.0100P)²+2.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2739
_refine_ls_number_parameters     233
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0926
_refine_ls_R_factor_gt           0.0514
_refine_ls_wR_factor_ref         0.1204
_refine_ls_wR_factor_gt          0.1046
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_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
C2 C 0.14310(15) 0.6732(2) 0.05670(13) 0.0465(6) Uani 1 1 d . . .
C10 C 0.26805(16) 0.5743(2) 0.04442(13) 0.0475(6) Uani 1 1 d . . .
C5 C 0.35726(17) 0.5640(3) 0.06182(16) 0.0610(7) Uani 1 1 d . . .
H5 H 0.3780 0.5029 0.0391 0.073 Uiso 1 1 calc R . .
C9 C 0.23466(15) 0.6668(2) 0.07804(13) 0.0459(6) Uani 1 1 d . . .
C3 C 0.09021(16) 0.5909(2) 0.00348(13) 0.0524(6) Uani 1 1 d . . .
H3 H 0.0302 0.5962 -0.0126 0.063 Uiso 1 1 calc R . .
C8 C 0.29594(17) 0.7467(2) 0.13178(14) 0.0596(7) Uani 1 1 d . . .
H8 H 0.2768 0.8071 0.1563 0.072 Uiso 1 1 calc R . .
C4 C 0.12644(17) 0.5002(2) -0.02611(14) 0.0548(7) Uani 1 1 d . . .
H4 H 0.0903 0.4431 -0.0605 0.066 Uiso 1 1 calc R . .
C6 C 0.41313(18) 0.6443(3) 0.11231(17) 0.0744(8) Uani 1 1 d . . .
H6 H 0.4724 0.6388 0.1236 0.089 Uiso 1 1 calc R . .
C1 C 0.10446(17) 0.7676(2) 0.08878(14) 0.0564(7) Uani 1 1 d . . .
H1 H 0.1336 0.8404 0.1086 0.068 Uiso 1 1 calc R . .
C7 C 0.38199(19) 0.7357(3) 0.14764(17) 0.0725(8) Uani 1 1 d . . .
H7 H 0.4211 0.7895 0.1824 0.087 Uiso 1 1 calc R . .
C12 C 0.24569(15) 0.8381(2) 0.33678(12) 0.0438(6) Uani 1 1 d . . .
C17 C 0.33319(15) 0.8495(2) 0.34934(12) 0.0447(6) Uani 1 1 d . . .
C16 C 0.35999(16) 0.9392(2) 0.30994(13) 0.0485(6) Uani 1 1 d . . .
C13 C 0.18520(16) 0.9160(2) 0.28319(14) 0.0537(7) Uani 1 1 d . . .
H13 H 0.1265 0.9084 0.2737 0.064 Uiso 1 1 calc R . .
C15 C 0.29895(17) 1.0147(2) 0.25843(14) 0.0554(7) Uani 1 1 d . . .
H15 H 0.3165 1.0744 0.2324 0.067 Uiso 1 1 calc R . .
C11 C 0.21631(18) 0.7453(2) 0.37939(14) 0.0507(6) Uani 1 1 d . . .
C14 C 0.21141(17) 1.0033(2) 0.24457(14) 0.0601(7) Uani 1 1 d . . .
H14 H 0.1707 1.0548 0.2092 0.072 Uiso 1 1 calc R . .
O2 O 0.13694(11) 0.73386(16) 0.36646(10) 0.0639(5) Uani 1 1 d . . .
O3 O 0.27461(11) 0.67725(16) 0.42813(10) 0.0620(5) Uani 1 1 d . . .
O4 O 0.39651(10) 0.77815(16) 0.40052(10) 0.0610(5) Uani 1 1 d . . .
H4A H 0.3746 0.7295 0.4208 0.092 Uiso 1 1 calc R . .
O5 O 0.44688(10) 0.94453(17) 0.32563(10) 0.0669(5) Uani 1 1 d . . .
H5A H 0.4566 1.0026 0.3025 0.100 Uiso 1 1 calc R . .
O6 O 0.0000 0.6203(2) 0.2500 0.0567(7) Uani 1 2 d S . .
O1 O -0.00046(12) 0.84526(17) 0.11791(12) 0.0756(6) Uani 1 1 d . . .
H1A H -0.0462 0.8275 0.1219 0.113 Uiso 1 1 calc R . .
N1 N 0.02822(15) 0.74605(19) 0.08856(12) 0.0602(6) Uani 1 1 d . . .
N2 N 0.21115(14) 0.49323(18) -0.00645(11) 0.0501(5) Uani 1 1 d . . .
H2 H 0.2384(17) 0.426(3) -0.0289(16) 0.098(10) Uiso 1 1 d . . .
H6A H 0.0407(19) 0.665(3) 0.2821(17) 0.115(13) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C2 C3 1.377(3) . ?
C2 C9 1.424(3) . ?
C2 C1 1.466(3) . ?
C10 N2 1.375(3) . ?
C10 C5 1.401(3) . ?
C10 C9 1.417(3) . ?
C5 C6 1.359(4) . ?
C9 C8 1.421(3) . ?
C3 C4 1.386(3) . ?
C8 C7 1.355(3) . ?
C4 N2 1.318(3) . ?
C6 C7 1.407(4) . ?
C1 N1 1.295(3) . ?
C12 C17 1.393(3) . ?
C12 C13 1.401(3) . ?
C12 C11 1.489(3) . ?
C17 O4 1.361(2) . ?
C17 C16 1.403(3) . ?
C16 O5 1.366(3) . ?
C16 C15 1.372(3) . ?
C13 C14 1.370(3) . ?
C15 C14 1.388(3) . ?
C11 O2 1.258(3) . ?
C11 O3 1.281(3) . ?
O1 N1 1.384(2) . ?

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
C3 C2 C9 119.1(2) . . ?
C3 C2 C1 119.8(2) . . ?
C9 C2 C1 121.2(2) . . ?
N2 C10 C5 119.6(2) . . ?
N2 C10 C9 118.9(2) . . ?
C5 C10 C9 121.5(2) . . ?
C6 C5 C10 119.2(3) . . ?
C10 C9 C8 117.0(2) . . ?
C10 C9 C2 118.5(2) . . ?
C8 C9 C2 124.5(2) . . ?
C2 C3 C4 120.0(2) . . ?
C7 C8 C9 120.6(2) . . ?
N2 C4 C3 121.3(2) . . ?
C5 C6 C7 120.5(3) . . ?
N1 C1 C2 117.6(2) . . ?
C8 C7 C6 121.1(3) . . ?
C17 C12 C13 118.8(2) . . ?
C17 C12 C11 121.0(2) . . ?
C13 C12 C11 120.2(2) . . ?
O4 C17 C12 122.9(2) . . ?
O4 C17 C16 116.8(2) . . ?
C12 C17 C16 120.3(2) . . ?
O5 C16 C15 124.1(2) . . ?
O5 C16 C17 116.7(2) . . ?
C15 C16 C17 119.2(2) . . ?
C14 C13 C12 120.8(2) . . ?
C16 C15 C14 121.1(2) . . ?
O2 C11 O3 122.0(2) . . ?
O2 C11 C12 120.6(2) . . ?
O3 C11 C12 117.4(2) . . ?
C13 C14 C15 119.7(2) . . ?
C1 N1 O1 110.6(2) . . ?
C4 N2 C10 122.2(2) . . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.043
####################################################################### 
# 
# 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_gsd
_database_code_depnum_ccdc_archive 'CCDC 1481867'
_audit_update_record             
;
2016-10-13 deposited with the CCDC.
2016-11-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H9 N2 O, C7 H5 O4, H2 O'
_chemical_formula_sum            'C17 H16 N2 O6'
_chemical_formula_weight         344.32

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'
_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                   14.9671(9)
_cell_length_b                   7.0737(4)
_cell_length_c                   15.0978(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.540(4)
_cell_angle_gamma                90.00
_cell_volume                     1588.04(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1513
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      18.90

_exptl_crystal_description       Needle
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             720
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.969
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_process_details   multi-scan

_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 and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19942
_diffrn_reflns_av_R_equivalents  0.0754
_diffrn_reflns_av_sigmaI/netI    0.0735
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.82
_diffrn_reflns_theta_max         25.24
_reflns_number_total             2847
_reflns_number_gt                1584
_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)+(0.0700P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2847
_refine_ls_number_parameters     241
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.1155
_refine_ls_R_factor_gt           0.0541
_refine_ls_wR_factor_ref         0.1535
_refine_ls_wR_factor_gt          0.1265
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.028
_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
C12 C 0.72629(18) 0.2051(4) 0.41331(18) 0.0380(7) Uani 1 1 d . . .
C17 C 0.81884(18) 0.1942(3) 0.44112(17) 0.0375(7) Uani 1 1 d . . .
C10 C 0.76911(18) 0.1909(4) 1.04479(17) 0.0382(7) Uani 1 1 d . . .
C2 C 0.65691(19) 0.1272(3) 0.91844(17) 0.0374(7) Uani 1 1 d . . .
C5 C 0.8586(2) 0.2137(4) 1.0834(2) 0.0490(8) Uani 1 1 d . . .
H5 H 0.8711 0.2391 1.1440 0.059 Uiso 1 1 calc R . .
C14 C 0.69911(19) 0.1259(4) 0.56394(18) 0.0459(7) Uani 1 1 d . . .
H14 H 0.6588 0.1059 0.6056 0.055 Uiso 1 1 calc R . .
C4 C 0.6157(2) 0.1847(4) 1.06513(18) 0.0456(7) Uani 1 1 d . . .
H4 H 0.5714 0.1946 1.1034 0.055 Uiso 1 1 calc R . .
C9 C 0.74892(17) 0.1497(4) 0.95309(17) 0.0364(7) Uani 1 1 d . . .
C16 C 0.85101(18) 0.1453(4) 0.52742(17) 0.0415(7) Uani 1 1 d . . .
H16 H 0.9126 0.1355 0.5440 0.050 Uiso 1 1 calc R . .
C11 C 0.6914(2) 0.2487(4) 0.31979(19) 0.0425(7) Uani 1 1 d . . .
C13 C 0.66835(19) 0.1703(4) 0.47756(18) 0.0436(7) Uani 1 1 d . . .
H13 H 0.6066 0.1775 0.4611 0.052 Uiso 1 1 calc R . .
C3 C 0.59121(19) 0.1472(4) 0.97579(18) 0.0444(7) Uani 1 1 d . . .
H3 H 0.5308 0.1353 0.9541 0.053 Uiso 1 1 calc R . .
C15 C 0.79146(19) 0.1108(4) 0.58894(18) 0.0418(7) Uani 1 1 d . . .
C8 C 0.8223(2) 0.1350(4) 0.90127(19) 0.0498(8) Uani 1 1 d . . .
H8 H 0.8115 0.1086 0.8407 0.060 Uiso 1 1 calc R . .
C6 C 0.9267(2) 0.1981(4) 1.0309(2) 0.0580(9) Uani 1 1 d . . .
H6 H 0.9859 0.2134 1.0560 0.070 Uiso 1 1 calc R . .
C1 C 0.6298(2) 0.0845(4) 0.82403(17) 0.0491(8) Uani 1 1 d . . .
H1 H 0.6685 0.1079 0.7813 0.059 Uiso 1 1 calc R . .
C7 C 0.9083(2) 0.1595(4) 0.9399(2) 0.0560(8) Uani 1 1 d . . .
H7 H 0.9556 0.1503 0.9051 0.067 Uiso 1 1 calc R . .
O4 O 0.87998(12) 0.2324(3) 0.38260(13) 0.0580(6) Uani 1 1 d . . .
H4A H 0.8533 0.2637 0.3344 0.087 Uiso 1 1 calc R . .
O5 O 0.81896(13) 0.0604(3) 0.67452(11) 0.0591(6) Uani 1 1 d . . .
H5A H 0.8737 0.0460 0.6808 0.089 Uiso 1 1 calc R . .
O3 O 0.74860(13) 0.2989(3) 0.26745(12) 0.0557(6) Uani 1 1 d . . .
O2 O 0.60930(13) 0.2361(3) 0.29461(13) 0.0598(6) Uani 1 1 d . . .
O6 O 1.00309(17) 0.9953(4) 0.29525(18) 0.0791(7) Uani 1 1 d D . .
O1 O 0.53439(14) -0.0103(3) 0.71116(11) 0.0710(7) Uani 1 1 d . . .
H1A H 0.4889 -0.0744 0.7000 0.107 Uiso 1 1 calc R . .
N2 N 0.70106(16) 0.2068(3) 1.09701(16) 0.0426(6) Uani 1 1 d D . .
N1 N 0.55184(17) 0.0144(3) 0.80212(14) 0.0508(7) Uani 1 1 d . . .
H2 H 0.7133(19) 0.236(4) 1.1561(13) 0.073(10) Uiso 1 1 d D . .
H6A H 0.9652(16) 0.923(4) 0.2631(17) 0.072(11) Uiso 1 1 d D . .
H6B H 0.966(2) 1.068(5) 0.317(2) 0.128(19) Uiso 1 1 d D . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C12 C13 1.395(3) . ?
C12 C17 1.403(4) . ?
C12 C11 1.481(4) . ?
C17 O4 1.369(3) . ?
C17 C16 1.381(3) . ?
C10 N2 1.362(3) . ?
C10 C5 1.407(4) . ?
C10 C9 1.413(3) . ?
C2 C3 1.389(4) . ?
C2 C9 1.425(4) . ?
C2 C1 1.468(3) . ?
C5 C6 1.365(4) . ?
C14 C13 1.369(3) . ?
C14 C15 1.395(4) . ?
C4 N2 1.322(3) . ?
C4 C3 1.383(4) . ?
C9 C8 1.423(4) . ?
C16 C15 1.380(3) . ?
C11 O2 1.248(3) . ?
C11 O3 1.279(3) . ?
C15 O5 1.358(3) . ?
C8 C7 1.362(4) . ?
C6 C7 1.397(4) . ?
C1 N1 1.276(3) . ?
O1 N1 1.380(2) . ?

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
C13 C12 C17 116.9(2) . . ?
C13 C12 C11 121.4(3) . . ?
C17 C12 C11 121.7(3) . . ?
O4 C17 C16 118.1(2) . . ?
O4 C17 C12 120.4(2) . . ?
C16 C17 C12 121.5(3) . . ?
N2 C10 C5 119.3(3) . . ?
N2 C10 C9 119.6(2) . . ?
C5 C10 C9 121.1(3) . . ?
C3 C2 C9 118.9(2) . . ?
C3 C2 C1 119.3(3) . . ?
C9 C2 C1 121.9(2) . . ?
C6 C5 C10 119.2(3) . . ?
C13 C14 C15 119.4(3) . . ?
N2 C4 C3 121.0(3) . . ?
C10 C9 C8 117.5(3) . . ?
C10 C9 C2 118.2(2) . . ?
C8 C9 C2 124.4(3) . . ?
C15 C16 C17 119.8(3) . . ?
O2 C11 O3 122.4(3) . . ?
O2 C11 C12 120.2(3) . . ?
O3 C11 C12 117.3(3) . . ?
C14 C13 C12 122.3(3) . . ?
C4 C3 C2 120.0(3) . . ?
O5 C15 C16 122.5(2) . . ?
O5 C15 C14 117.5(2) . . ?
C16 C15 C14 120.0(3) . . ?
C7 C8 C9 120.4(3) . . ?
C5 C6 C7 120.7(3) . . ?
N1 C1 C2 118.4(3) . . ?
C8 C7 C6 121.1(3) . . ?
C4 N2 C10 122.3(2) . . ?
C1 N1 O1 111.8(2) . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.044
