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

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

data_Ia
_database_code_depnum_ccdc_archive 'CCDC 1045622'
_audit_update_record             
;
2015-01-26 deposited with the CCDC.
2016-01-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_symmetry_space_group_name_Hall  '-P 2ybc'
_chemical_formula_moiety         'C9 H11 N3 O, C7 H6 O4'
_chemical_formula_sum            'C16 H17 N3 O5'
_chemical_formula_weight         331.33

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           MONOCLINIC
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   15.2726(7)
_cell_length_b                   11.5810(5)
_cell_length_c                   9.1189(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.0230(10)
_cell_angle_gamma                90.00
_cell_volume                     1606.68(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       PLATE
_exptl_crystal_colour            COLORLESS
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9500
_exptl_absorpt_correction_T_max  0.9907
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'BRUKER CCD AREA'
_diffrn_measurement_method       'PHI-OMEGA SCAN'
_diffrn_detector_area_resol_mean 3
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18715
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_sigmaI/netI    0.0180
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.34
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2832
_reflns_number_gt                2179
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART APEX II'
_computing_cell_refinement       'SMART APEX II'
_computing_data_reduction        'SMART APEX SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  'MERCURY 2.3'

_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)+(0.0791P)²+0.2534P] 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         2832
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0415
_refine_ls_wR_factor_ref         0.1425
_refine_ls_wR_factor_gt          0.1125
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_restrained_S_all      1.117
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.37921(12) 0.75603(16) 0.4531(2) 0.0475(5) Uani 1 1 d . . .
O2 O 0.41459(9) 0.84970(12) 0.51091(17) 0.0602(4) Uani 1 1 d . . .
H2 H 0.4529 0.8324 0.5758 0.090 Uiso 1 1 calc R . .
O3 O 0.40601(10) 0.65890(12) 0.48763(17) 0.0647(4) Uani 1 1 d . . .
C4 C 0.30509(12) 0.77510(15) 0.3410(2) 0.0425(4) Uani 1 1 d . . .
C5 C 0.26615(14) 0.68100(16) 0.2633(2) 0.0502(5) Uani 1 1 d . . .
O6 O 0.29320(12) 0.57093(12) 0.29167(19) 0.0733(5) Uani 1 1 d . . .
H6 H 0.3356 0.5714 0.3534 0.110 Uiso 1 1 calc R . .
C7 C 0.19852(15) 0.70090(18) 0.1559(2) 0.0583(6) Uani 1 1 d . . .
H7 H 0.1740 0.6392 0.1014 0.070 Uiso 1 1 calc R . .
C8 C 0.16695(14) 0.81029(17) 0.1284(2) 0.0531(5) Uani 1 1 d . . .
H8 H 0.1212 0.8220 0.0557 0.064 Uiso 1 1 calc R . .
C9 C 0.20256(12) 0.90351(15) 0.2079(2) 0.0433(4) Uani 1 1 d . . .
O10 O 0.16673(9) 1.01064(11) 0.17616(15) 0.0567(4) Uani 1 1 d . . .
H10 H 0.1826 1.0558 0.2425 0.085 Uiso 1 1 calc R . .
C11 C 0.27203(11) 0.88551(15) 0.3118(2) 0.0416(4) Uani 1 1 d . . .
H11 H 0.2973 0.9481 0.3634 0.050 Uiso 1 1 calc R . .
C12 C 0.75155(12) 0.73001(15) 0.0411(2) 0.0452(5) Uani 1 1 d . . .
O13 O 0.75641(11) 0.63106(12) 0.08627(18) 0.0729(5) Uani 1 1 d . . .
N14 N 0.80614(11) 0.81312(14) 0.09355(19) 0.0494(4) Uani 1 1 d . . .
N15 N 0.86409(12) 0.78660(15) 0.21529(19) 0.0579(5) Uani 1 1 d . . .
C16 C 0.92160(12) 0.86232(18) 0.2559(2) 0.0518(5) Uani 1 1 d . . .
C17 C 0.93485(15) 0.97443(19) 0.1817(3) 0.0682(6) Uani 1 1 d . . .
H17A H 0.9392 0.9615 0.0786 0.102 Uiso 1 1 calc R . .
H17B H 0.9880 1.0098 0.2241 0.102 Uiso 1 1 calc R . .
H17C H 0.8859 1.0244 0.1943 0.102 Uiso 1 1 calc R . .
C18 C 0.98106(17) 0.8326(3) 0.3901(3) 0.0839(8) Uani 1 1 d . . .
H18A H 0.9707 0.7543 0.4182 0.126 Uiso 1 1 calc R . .
H18B H 0.9694 0.8835 0.4692 0.126 Uiso 1 1 calc R . .
H18C H 1.0412 0.8411 0.3687 0.126 Uiso 1 1 calc R . .
C19 C 0.68015(12) 0.76265(15) -0.07456(19) 0.0400(4) Uani 1 1 d . . .
C20 C 0.63745(13) 0.67434(16) -0.1545(2) 0.0480(5) Uani 1 1 d . . .
H20 H 0.6543 0.5979 -0.1384 0.058 Uiso 1 1 calc R . .
C21 C 0.56944(13) 0.70178(17) -0.2585(2) 0.0506(5) Uani 1 1 d . . .
H21 H 0.5415 0.6422 -0.3126 0.061 Uiso 1 1 calc R . .
N22 N 0.54205(10) 0.80924(14) -0.28490(19) 0.0509(4) Uani 1 1 d . . .
C23 C 0.58267(13) 0.89368(17) -0.2069(2) 0.0538(5) Uani 1 1 d . . .
H23 H 0.5637 0.9692 -0.2241 0.065 Uiso 1 1 calc R . .
C24 C 0.65140(12) 0.87444(16) -0.1019(2) 0.0474(5) Uani 1 1 d . . .
H24 H 0.6782 0.9359 -0.0500 0.057 Uiso 1 1 calc R . .
H14 H 0.8069(15) 0.879(2) 0.046(2) 0.066(7) 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
C1 O3 1.229(2) . ?
C1 O2 1.303(2) . ?
C1 C4 1.474(3) . ?
O2 H2 0.8200 . ?
C4 C11 1.392(3) . ?
C4 C5 1.403(3) . ?
C5 O6 1.358(2) . ?
C5 C7 1.379(3) . ?
O6 H6 0.8200 . ?
C7 C8 1.371(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.385(3) . ?
C8 H8 0.9300 . ?
C9 C11 1.375(3) . ?
C9 O10 1.376(2) . ?
O10 H10 0.8200 . ?
C11 H11 0.9300 . ?
C12 O13 1.218(2) . ?
C12 N14 1.334(2) . ?
C12 C19 1.498(3) . ?
N14 N15 1.392(2) . ?
N14 H14 0.87(2) . ?
N15 C16 1.273(2) . ?
C16 C17 1.486(3) . ?
C16 C18 1.498(3) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C24 1.383(3) . ?
C19 C20 1.385(2) . ?
C20 C21 1.381(3) . ?
C20 H20 0.9300 . ?
C21 N22 1.328(2) . ?
C21 H21 0.9300 . ?
N22 C23 1.330(2) . ?
C23 C24 1.375(3) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 C1 O2 122.79(18) . . ?
O3 C1 C4 122.24(18) . . ?
O2 C1 C4 114.97(16) . . ?
C1 O2 H2 109.5 . . ?
C11 C4 C5 119.09(17) . . ?
C11 C4 C1 120.94(17) . . ?
C5 C4 C1 119.97(17) . . ?
O6 C5 C7 119.24(18) . . ?
O6 C5 C4 121.64(19) . . ?
C7 C5 C4 119.12(18) . . ?
C5 O6 H6 109.5 . . ?
C8 C7 C5 120.93(18) . . ?
C8 C7 H7 119.5 . . ?
C5 C7 H7 119.5 . . ?
C7 C8 C9 120.59(19) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C11 C9 O10 123.36(16) . . ?
C11 C9 C8 119.11(17) . . ?
O10 C9 C8 117.51(16) . . ?
C9 O10 H10 109.5 . . ?
C9 C11 C4 121.07(17) . . ?
C9 C11 H11 119.5 . . ?
C4 C11 H11 119.5 . . ?
O13 C12 N14 122.67(18) . . ?
O13 C12 C19 119.65(17) . . ?
N14 C12 C19 117.64(16) . . ?
C12 N14 N15 117.41(16) . . ?
C12 N14 H14 118.9(15) . . ?
N15 N14 H14 123.5(15) . . ?
C16 N15 N14 117.03(17) . . ?
N15 C16 C17 125.95(18) . . ?
N15 C16 C18 115.67(19) . . ?
C17 C16 C18 118.38(19) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C24 C19 C20 117.96(17) . . ?
C24 C19 C12 124.30(17) . . ?
C20 C19 C12 117.67(16) . . ?
C21 C20 C19 118.85(17) . . ?
C21 C20 H20 120.6 . . ?
C19 C20 H20 120.6 . . ?
N22 C21 C20 123.11(18) . . ?
N22 C21 H21 118.4 . . ?
C20 C21 H21 118.4 . . ?
C21 N22 C23 117.84(17) . . ?
N22 C23 C24 123.01(18) . . ?
N22 C23 H23 118.5 . . ?
C24 C23 H23 118.5 . . ?
C23 C24 C19 119.23(18) . . ?
C23 C24 H24 120.4 . . ?
C19 C24 H24 120.4 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 N22 0.82 1.80 2.616(2) 173.9 1_556
O10 H10 O13 0.82 1.95 2.7515(18) 164.7 2_655

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.081
####################################################################### 
# 
# 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_Ib_1045623
_database_code_depnum_ccdc_archive 'CCDC 1045623'
_audit_update_record             
;
2015-07-28 deposited with the CCDC.
2016-01-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H19 N3 O9'
_chemical_formula_weight         445.38

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

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

_cell_length_a                   7.6313(7)
_cell_length_b                   7.8438(7)
_cell_length_c                   17.8835(17)
_cell_angle_alpha                81.836(3)
_cell_angle_beta                 88.720(3)
_cell_angle_gamma                64.742(3)
_cell_volume                     957.45(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Rod
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.545
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             464
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9661
_exptl_absorpt_correction_T_max  0.9938
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker ApexII CCD'
_diffrn_measurement_method       'w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11342
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_sigmaI/netI    0.0298
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.15
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3313
_reflns_number_gt                2414
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0836P)²+0.1281P] 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         3313
_refine_ls_number_parameters     313
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0392
_refine_ls_wR_factor_ref         0.1232
_refine_ls_wR_factor_gt          0.1034
_refine_ls_goodness_of_fit_ref   0.908
_refine_ls_restrained_S_all      0.908
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C13 C 0.1691(3) 0.2520(3) 0.42363(11) 0.0412(4) Uani 1 1 d . . .
O2 O 0.2477(2) 0.1546(2) 0.48770(8) 0.0615(4) Uani 1 1 d . . .
O3 O 0.1480(2) 0.4191(2) 0.40467(8) 0.0567(4) Uani 1 1 d . . .
C12 C 0.1013(2) 0.1584(2) 0.37241(9) 0.0355(4) Uani 1 1 d . . .
C7 C 0.0221(3) 0.2526(3) 0.29978(10) 0.0418(5) Uani 1 1 d . . .
O5 O 0.0080(2) 0.4311(2) 0.27627(8) 0.0566(4) Uani 1 1 d . . .
H13 H 0.0454 0.4678 0.3107 0.085 Uiso 1 1 calc R . .
C8 C -0.0443(3) 0.1687(4) 0.25185(11) 0.0547(6) Uani 1 1 d . . .
H9 H -0.0943 0.2315 0.2036 0.066 Uiso 1 1 calc R . .
C9 C -0.0361(3) -0.0091(4) 0.27600(13) 0.0597(6) Uani 1 1 d . . .
H10 H -0.0818 -0.0653 0.2436 0.072 Uiso 1 1 calc R . .
C10 C 0.0379(3) -0.1056(3) 0.34651(13) 0.0524(5) Uani 1 1 d . . .
H11 H 0.0404 -0.2249 0.3620 0.063 Uiso 1 1 calc R . .
C11 C 0.1092(3) -0.0231(3) 0.39480(10) 0.0407(4) Uani 1 1 d . . .
O4 O 0.1895(2) -0.12478(19) 0.46216(8) 0.0590(4) Uani 1 1 d . . .
H12 H 0.2218 -0.0607 0.4863 0.088 Uiso 1 1 calc R . .
C20 C 0.2504(3) -0.1585(2) 1.05595(9) 0.0348(4) Uani 1 1 d . . .
O6 O 0.2809(2) -0.31839(17) 1.03720(7) 0.0457(4) Uani 1 1 d . . .
O7 O 0.2155(2) -0.12344(17) 1.12323(7) 0.0441(3) Uani 1 1 d . . .
C19 C 0.2561(2) -0.0072(2) 0.99753(9) 0.0325(4) Uani 1 1 d . . .
C14 C 0.2112(2) 0.1754(2) 1.01440(9) 0.0369(4) Uani 1 1 d . . .
O8 O 0.1614(2) 0.21867(18) 1.08483(7) 0.0486(4) Uani 1 1 d . . .
H17 H 0.1662 0.1238 1.1125 0.073 Uiso 1 1 calc R . .
C15 C 0.2174(3) 0.3173(3) 0.95966(11) 0.0446(5) Uani 1 1 d . . .
H14 H 0.1858 0.4387 0.9712 0.054 Uiso 1 1 calc R . .
C16 C 0.2710(3) 0.2749(3) 0.88790(11) 0.0477(5) Uani 1 1 d . . .
H15 H 0.2747 0.3697 0.8510 0.057 Uiso 1 1 calc R . .
C17 C 0.3195(3) 0.0956(3) 0.86944(10) 0.0455(5) Uani 1 1 d . . .
H16 H 0.3576 0.0695 0.8210 0.055 Uiso 1 1 calc R . .
C18 C 0.3109(3) -0.0443(3) 0.92357(10) 0.0378(4) Uani 1 1 d . . .
O9 O 0.3607(2) -0.21917(19) 0.90376(7) 0.0508(4) Uani 1 1 d . . .
H18 H 0.3424 -0.2881 0.9390 0.076 Uiso 1 1 calc R . .
C6 C 0.4469(3) 0.4223(2) 0.27039(9) 0.0337(4) Uani 1 1 d . . .
O1 O 0.48347(19) 0.25463(17) 0.28469(7) 0.0461(3) Uani 1 1 d . . .
N2 N 0.3393(2) 0.5332(2) 0.20843(8) 0.0427(4) Uani 1 1 d . . .
N3 N 0.2748(3) 0.4460(3) 0.15844(9) 0.0426(4) Uani 1 1 d . . .
C5 C 0.5167(2) 0.5234(2) 0.31966(9) 0.0333(4) Uani 1 1 d . . .
C1 C 0.6067(3) 0.4233(3) 0.38892(10) 0.0412(4) Uani 1 1 d . . .
H1 H 0.6220 0.2989 0.4034 0.049 Uiso 1 1 calc R . .
C2 C 0.6728(3) 0.5088(3) 0.43578(10) 0.0444(5) Uani 1 1 d . . .
H2 H 0.7332 0.4420 0.4823 0.053 Uiso 1 1 calc R . .
N1 N 0.6517(2) 0.6861(2) 0.41547(9) 0.0420(4) Uani 1 1 d . . .
C3 C 0.5665(3) 0.7871(3) 0.34891(10) 0.0431(5) Uani 1 1 d . . .
H3 H 0.5537 0.9110 0.3359 0.052 Uiso 1 1 calc R . .
C4 C 0.4978(3) 0.7074(3) 0.29980(10) 0.0383(4) Uani 1 1 d . . .
H4 H 0.4389 0.7770 0.2535 0.046 Uiso 1 1 calc R . .
H7 H 0.168(4) 0.427(3) 0.1779(14) 0.064(7) Uiso 1 1 d . . .
H30 H 0.690(4) 0.751(3) 0.4515(15) 0.079(7) Uiso 1 1 d . . .
H8 H 0.366(4) 0.336(4) 0.1508(14) 0.069(8) Uiso 1 1 d . . .
H6 H 0.244(4) 0.540(4) 0.1061(16) 0.086(8) Uiso 1 1 d . . .
H5 H 0.311(3) 0.660(3) 0.1920(12) 0.057(6) 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
C13 O3 1.247(2) . ?
C13 O2 1.283(2) . ?
C13 C12 1.477(3) . ?
C12 C11 1.399(3) . ?
C12 C7 1.407(2) . ?
C7 O5 1.361(2) . ?
C7 C8 1.375(3) . ?
O5 H13 0.8200 . ?
C8 C9 1.375(3) . ?
C8 H9 0.9300 . ?
C9 C10 1.370(3) . ?
C9 H10 0.9300 . ?
C10 C11 1.393(3) . ?
C10 H11 0.9300 . ?
C11 O4 1.344(2) . ?
O4 H12 0.8200 . ?
C20 O6 1.267(2) . ?
C20 O7 1.270(2) . ?
C20 C19 1.481(2) . ?
C19 C14 1.400(2) . ?
C19 C18 1.410(2) . ?
C14 O8 1.355(2) . ?
C14 C15 1.390(2) . ?
O8 H17 0.8200 . ?
C15 C16 1.381(3) . ?
C15 H14 0.9300 . ?
C16 C17 1.381(3) . ?
C16 H15 0.9300 . ?
C17 C18 1.380(3) . ?
C17 H16 0.9300 . ?
C18 O9 1.356(2) . ?
O9 H18 0.8200 . ?
C6 O1 1.211(2) . ?
C6 N2 1.348(2) . ?
C6 C5 1.506(2) . ?
N2 N3 1.410(2) . ?
N2 H5 0.93(2) . ?
N3 H7 0.94(3) . ?
N3 H8 0.88(3) . ?
N3 H6 1.07(3) . ?
C5 C4 1.382(2) . ?
C5 C1 1.387(2) . ?
C1 C2 1.369(3) . ?
C1 H1 0.9300 . ?
C2 N1 1.327(2) . ?
C2 H2 0.9300 . ?
N1 C3 1.340(2) . ?
N1 H30 0.99(3) . ?
C3 C4 1.376(3) . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 C13 O2 122.40(17) . . ?
O3 C13 C12 120.50(17) . . ?
O2 C13 C12 117.10(16) . . ?
C11 C12 C7 118.03(17) . . ?
C11 C12 C13 121.52(16) . . ?
C7 C12 C13 120.43(16) . . ?
O5 C7 C8 118.86(18) . . ?
O5 C7 C12 119.98(17) . . ?
C8 C7 C12 121.16(19) . . ?
C7 O5 H13 109.5 . . ?
C7 C8 C9 119.24(19) . . ?
C7 C8 H9 120.4 . . ?
C9 C8 H9 120.4 . . ?
C10 C9 C8 121.73(19) . . ?
C10 C9 H10 119.1 . . ?
C8 C9 H10 119.1 . . ?
C9 C10 C11 119.4(2) . . ?
C9 C10 H11 120.3 . . ?
C11 C10 H11 120.3 . . ?
O4 C11 C10 118.09(18) . . ?
O4 C11 C12 121.42(17) . . ?
C10 C11 C12 120.46(18) . . ?
C11 O4 H12 109.5 . . ?
O6 C20 O7 122.32(15) . . ?
O6 C20 C19 119.00(15) . . ?
O7 C20 C19 118.69(15) . . ?
C14 C19 C18 118.08(15) . . ?
C14 C19 C20 121.08(15) . . ?
C18 C19 C20 120.82(15) . . ?
O8 C14 C15 118.04(16) . . ?
O8 C14 C19 120.85(15) . . ?
C15 C14 C19 121.11(16) . . ?
C14 O8 H17 109.5 . . ?
C16 C15 C14 118.86(18) . . ?
C16 C15 H14 120.6 . . ?
C14 C15 H14 120.6 . . ?
C17 C16 C15 121.73(17) . . ?
C17 C16 H15 119.1 . . ?
C15 C16 H15 119.1 . . ?
C18 C17 C16 119.32(18) . . ?
C18 C17 H16 120.3 . . ?
C16 C17 H16 120.3 . . ?
O9 C18 C17 117.84(16) . . ?
O9 C18 C19 121.26(15) . . ?
C17 C18 C19 120.89(17) . . ?
C18 O9 H18 109.5 . . ?
O1 C6 N2 122.01(16) . . ?
O1 C6 C5 123.25(15) . . ?
N2 C6 C5 114.74(15) . . ?
C6 N2 N3 117.66(15) . . ?
C6 N2 H5 127.3(14) . . ?
N3 N2 H5 114.8(14) . . ?
N2 N3 H7 110.1(14) . . ?
N2 N3 H8 112.2(16) . . ?
H7 N3 H8 108(2) . . ?
N2 N3 H6 104.2(14) . . ?
H7 N3 H6 114(2) . . ?
H8 N3 H6 108(2) . . ?
C4 C5 C1 118.59(16) . . ?
C4 C5 C6 124.12(15) . . ?
C1 C5 C6 117.29(15) . . ?
C2 C1 C5 119.55(17) . . ?
C2 C1 H1 120.2 . . ?
C5 C1 H1 120.2 . . ?
N1 C2 C1 120.58(17) . . ?
N1 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 N1 C3 121.63(17) . . ?
C2 N1 H30 120.0(14) . . ?
C3 N1 H30 118.2(15) . . ?
N1 C3 C4 119.99(17) . . ?
N1 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C5 119.65(16) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H5 O7 0.93(2) 1.82(2) 2.6823(19) 153(2) 1_564
N3 H6 O7 1.07(3) 2.61(3) 3.180(2) 112.5(17) 1_564
N3 H6 O6 1.07(3) 1.64(3) 2.655(2) 157(2) 1_564
N1 H30 O2 0.99(3) 1.59(3) 2.577(2) 177(2) 2_666

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.042
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Ic_1045624
_database_code_depnum_ccdc_archive 'CCDC 1045624'
_audit_update_record             
;
2015-07-28 deposited with the CCDC.
2016-01-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H18 N4 O3'
_chemical_formula_weight         314.34

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/c

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

_cell_length_a                   8.7707(4)
_cell_length_b                   20.4025(9)
_cell_length_c                   9.1687(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.5140(10)
_cell_angle_gamma                90.00
_cell_volume                     1613.14(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Needle
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.71
_exptl_crystal_size_mid          0.65
_exptl_crystal_size_min          0.39
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9375
_exptl_absorpt_correction_T_max  0.9650
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker ApexII CCD'
_diffrn_measurement_method       'w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18565
_diffrn_reflns_av_R_equivalents  0.0192
_diffrn_reflns_av_sigmaI/netI    0.0104
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.47
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2844
_reflns_number_gt                2503
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.1000P)²+0.4029P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.014(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2844
_refine_ls_number_parameters     224
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0399
_refine_ls_wR_factor_ref         0.1413
_refine_ls_wR_factor_gt          0.1273
_refine_ls_goodness_of_fit_ref   0.929
_refine_ls_restrained_S_all      0.929
_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
C7 C 0.4969(2) 0.61368(8) 0.82277(18) 0.0545(4) Uani 1 1 d . . .
C8 C 0.5937(3) 0.56694(10) 0.7534(3) 0.0794(6) Uani 1 1 d . . .
H8 H 0.6328 0.5886 0.6749 0.119 Uiso 1 1 calc R . .
H6 H 0.5315 0.5301 0.7138 0.119 Uiso 1 1 calc R . .
H7 H 0.6789 0.5521 0.8269 0.119 Uiso 1 1 calc R . .
C9 C 0.4159(3) 0.58695(8) 0.9398(2) 0.0698(5) Uani 1 1 d . . .
H11 H 0.4862 0.5863 1.0332 0.105 Uiso 1 1 calc R . .
H10 H 0.3809 0.5432 0.9137 0.105 Uiso 1 1 calc R . .
H9 H 0.3285 0.6142 0.9476 0.105 Uiso 1 1 calc R . .
N3 N 0.49220(16) 0.67274(6) 0.77585(15) 0.0532(4) Uani 1 1 d . . .
N2 N 0.40626(16) 0.71674(6) 0.84559(15) 0.0484(3) Uani 1 1 d . . .
C6 C 0.38113(18) 0.77716(7) 0.78679(16) 0.0451(4) Uani 1 1 d . . .
O1 O 0.41476(16) 0.79355(5) 0.66831(12) 0.0607(4) Uani 1 1 d . . .
C5 C 0.30537(17) 0.82446(7) 0.87614(15) 0.0438(4) Uani 1 1 d . . .
C1 C 0.20030(18) 0.80602(7) 0.96333(18) 0.0500(4) Uani 1 1 d . . .
H1 H 0.1735 0.7622 0.9702 0.060 Uiso 1 1 calc R . .
C2 C 0.13544(19) 0.85332(8) 1.0401(2) 0.0555(4) Uani 1 1 d . . .
H2 H 0.0628 0.8404 1.0966 0.067 Uiso 1 1 calc R . .
N1 N 0.17163(18) 0.91654(7) 1.03737(16) 0.0571(4) Uani 1 1 d . . .
C3 C 0.2724(2) 0.93391(8) 0.9527(2) 0.0654(5) Uani 1 1 d . . .
H3 H 0.2981 0.9780 0.9488 0.078 Uiso 1 1 calc R . .
C4 C 0.3409(2) 0.89013(8) 0.8702(2) 0.0607(5) Uani 1 1 d . . .
H4 H 0.4101 0.9046 0.8115 0.073 Uiso 1 1 calc R . .
C16 C 0.1705(2) 0.43667(8) 0.7167(2) 0.0582(4) Uani 1 1 d . . .
O3 O 0.09730(17) 0.49275(6) 0.72332(16) 0.0691(4) Uani 1 1 d . . .
H18 H 0.1168 0.5175 0.6587 0.104 Uiso 1 1 calc R . .
O2 O 0.2506(2) 0.42534(7) 0.62509(19) 0.0929(6) Uani 1 1 d . . .
C15 C 0.14500(18) 0.38848(8) 0.83197(18) 0.0524(4) Uani 1 1 d . . .
C14 C 0.22096(19) 0.32891(8) 0.83717(18) 0.0540(4) Uani 1 1 d . . .
H15 H 0.2854 0.3204 0.7693 0.065 Uiso 1 1 calc R . .
C13 C 0.20312(19) 0.28123(9) 0.94187(18) 0.0548(4) Uani 1 1 d . . .
N4 N 0.2748(2) 0.22126(9) 0.9425(2) 0.0755(5) Uani 1 1 d . . .
C12 C 0.1107(2) 0.29685(10) 1.0449(2) 0.0646(5) Uani 1 1 d . . .
H14 H 0.0997 0.2668 1.1185 0.078 Uiso 1 1 calc R . .
C11 C 0.0351(2) 0.35614(11) 1.0398(2) 0.0738(6) Uani 1 1 d . . .
H13 H -0.0267 0.3652 1.1097 0.089 Uiso 1 1 calc R . .
C10 C 0.0490(2) 0.40265(10) 0.9324(2) 0.0657(5) Uani 1 1 d . . .
H12 H -0.0046 0.4422 0.9280 0.079 Uiso 1 1 calc R . .
H16 H 0.259(3) 0.1932(12) 1.007(3) 0.082(7) Uiso 1 1 d . . .
H17 H 0.337(3) 0.2148(12) 0.876(3) 0.083(7) Uiso 1 1 d . . .
H5 H 0.406(2) 0.7114(10) 0.939(3) 0.071(6) 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
C7 N3 1.278(2) . ?
C7 C8 1.494(2) . ?
C7 C9 1.494(3) . ?
C8 H8 0.9600 . ?
C8 H6 0.9600 . ?
C8 H7 0.9600 . ?
C9 H11 0.9600 . ?
C9 H10 0.9600 . ?
C9 H9 0.9600 . ?
N3 N2 1.3995(18) . ?
N2 C6 1.347(2) . ?
N2 H5 0.86(2) . ?
C6 O1 1.2230(18) . ?
C6 C5 1.498(2) . ?
C5 C1 1.378(2) . ?
C5 C4 1.379(2) . ?
C1 C2 1.377(2) . ?
C1 H1 0.9300 . ?
C2 N1 1.330(2) . ?
C2 H2 0.9300 . ?
N1 C3 1.326(2) . ?
C3 C4 1.378(2) . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?
C16 O2 1.212(2) . ?
C16 O3 1.319(2) . ?
C16 C15 1.490(2) . ?
O3 H18 0.8200 . ?
C15 C14 1.383(3) . ?
C15 C10 1.387(2) . ?
C14 C13 1.395(2) . ?
C14 H15 0.9300 . ?
C13 N4 1.375(3) . ?
C13 C12 1.389(3) . ?
N4 H16 0.85(3) . ?
N4 H17 0.90(3) . ?
C12 C11 1.376(3) . ?
C12 H14 0.9300 . ?
C11 C10 1.388(3) . ?
C11 H13 0.9300 . ?
C10 H12 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 C7 C8 116.40(17) . . ?
N3 C7 C9 126.57(15) . . ?
C8 C7 C9 117.03(16) . . ?
C7 C8 H8 109.5 . . ?
C7 C8 H6 109.5 . . ?
H8 C8 H6 109.5 . . ?
C7 C8 H7 109.5 . . ?
H8 C8 H7 109.5 . . ?
H6 C8 H7 109.5 . . ?
C7 C9 H11 109.5 . . ?
C7 C9 H10 109.5 . . ?
H11 C9 H10 109.5 . . ?
C7 C9 H9 109.5 . . ?
H11 C9 H9 109.5 . . ?
H10 C9 H9 109.5 . . ?
C7 N3 N2 115.98(14) . . ?
C6 N2 N3 117.80(13) . . ?
C6 N2 H5 118.7(14) . . ?
N3 N2 H5 118.3(14) . . ?
O1 C6 N2 123.86(14) . . ?
O1 C6 C5 120.84(13) . . ?
N2 C6 C5 115.29(12) . . ?
C1 C5 C4 117.91(14) . . ?
C1 C5 C6 123.51(13) . . ?
C4 C5 C6 118.58(13) . . ?
C2 C1 C5 119.19(14) . . ?
C2 C1 H1 120.4 . . ?
C5 C1 H1 120.4 . . ?
N1 C2 C1 123.21(15) . . ?
N1 C2 H2 118.4 . . ?
C1 C2 H2 118.4 . . ?
C3 N1 C2 117.20(14) . . ?
N1 C3 C4 123.52(15) . . ?
N1 C3 H3 118.2 . . ?
C4 C3 H3 118.2 . . ?
C3 C4 C5 118.93(15) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
O2 C16 O3 123.10(16) . . ?
O2 C16 C15 123.16(17) . . ?
O3 C16 C15 113.73(15) . . ?
C16 O3 H18 109.5 . . ?
C14 C15 C10 120.50(16) . . ?
C14 C15 C16 118.08(15) . . ?
C10 C15 C16 121.41(17) . . ?
C15 C14 C13 121.51(16) . . ?
C15 C14 H15 119.2 . . ?
C13 C14 H15 119.2 . . ?
N4 C13 C12 121.62(17) . . ?
N4 C13 C14 120.97(17) . . ?
C12 C13 C14 117.41(17) . . ?
C13 N4 H16 117.9(16) . . ?
C13 N4 H17 117.4(16) . . ?
H16 N4 H17 125(2) . . ?
C11 C12 C13 121.05(17) . . ?
C11 C12 H14 119.5 . . ?
C13 C12 H14 119.5 . . ?
C12 C11 C10 121.39(18) . . ?
C12 C11 H13 119.3 . . ?
C10 C11 H13 119.3 . . ?
C15 C10 C11 118.07(19) . . ?
C15 C10 H12 121.0 . . ?
C11 C10 H12 121.0 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H5 O1 0.86(2) 2.09(2) 2.9538(17) 175(2) 4_576
N4 H17 N3 0.90(3) 2.38(3) 3.264(3) 167(2) 2_646
N4 H16 O2 0.85(3) 2.66(3) 3.453(2) 156(2) 4_566
O3 H18 N1 0.82 1.86 2.6763(18) 170.5 4_575

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.031
####################################################################### 
# 
# 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_Id_1045625
_database_code_depnum_ccdc_archive 'CCDC 1045625'
_audit_update_record             
;
2015-07-28 deposited with the CCDC.
2016-01-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H2 N3 O5'
_chemical_formula_weight         303.27

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

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   6.9555(3)
_cell_length_b                   9.2797(4)
_cell_length_c                   11.0293(5)
_cell_angle_alpha                97.828(2)
_cell_angle_beta                 99.815(3)
_cell_angle_gamma                100.154(2)
_cell_volume                     680.26(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Plate
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             272
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker ApexII CCD'
_diffrn_measurement_method       'w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4341
_diffrn_reflns_av_R_equivalents  0.0156
_diffrn_reflns_av_sigmaI/netI    0.0280
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.90
_diffrn_reflns_theta_max         26.00
_reflns_number_total             2582
_reflns_number_gt                2120
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2582
_refine_ls_number_parameters     215
_refine_ls_number_restraints     50
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0450
_refine_ls_wR_factor_ref         0.1497
_refine_ls_wR_factor_gt          0.1393
_refine_ls_goodness_of_fit_ref   1.150
_refine_ls_restrained_S_all      1.138
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.78976(17) 0.52875(13) 0.90097(10) 0.0532(4) Uani 1 1 d U . .
O2 O 0.79689(16) 0.67142(13) 0.60798(11) 0.0539(4) Uani 1 1 d U . .
O3 O 0.83173(18) 0.85986(14) 0.75778(11) 0.0601(4) Uani 1 1 d U . .
O4 O 0.65704(19) 1.04289(13) 0.82780(10) 0.0573(4) Uani 1 1 d U . .
N2 N 0.77778(18) 0.70873(13) 1.05639(10) 0.0383(3) Uani 1 1 d U . .
H6 H 0.7171 0.7767 1.0816 0.046 Uiso 1 1 calc R . .
N1 N 0.13749(18) 0.64464(15) 0.74592(11) 0.0405(3) Uani 1 1 d U . .
O5 O 0.3742(2) 1.11066(16) 0.77457(12) 0.0751(5) Uani 1 1 d U . .
N3 N 0.9572(2) 0.69340(18) 1.13095(11) 0.0446(4) Uani 1 1 d U . .
C5 C 0.4986(2) 0.63144(15) 0.88256(11) 0.0317(3) Uani 1 1 d U . .
C8 C 0.5358(2) 0.80516(15) 0.59397(11) 0.0314(3) Uani 1 1 d U . .
C6 C 0.7021(2) 0.61895(16) 0.94774(12) 0.0336(3) Uani 1 1 d U . .
C14 C 0.7340(2) 0.77776(16) 0.65672(13) 0.0366(4) Uani 1 1 d U . .
C7 C 0.4316(2) 0.91471(14) 0.63437(11) 0.0338(3) Uani 1 1 d U . .
C4 C 0.4125(2) 0.52930(17) 0.77410(13) 0.0397(4) Uani 1 1 d U . .
H5 H 0.4771 0.4550 0.7471 0.048 Uiso 1 1 calc R . .
C9 C 0.4500(2) 0.70747(16) 0.48194(12) 0.0385(4) Uani 1 1 d U . .
H9 H 0.5164 0.6342 0.4552 0.046 Uiso 1 1 calc R . .
C2 C 0.2146(2) 0.74166(19) 0.85157(14) 0.0445(4) Uani 1 1 d U . .
H2 H 0.1446 0.8126 0.8779 0.053 Uiso 1 1 calc R . .
C13 C 0.4891(2) 1.03071(16) 0.75267(14) 0.0441(4) Uani 1 1 d U . .
C1 C 0.3961(2) 0.73771(17) 0.92171(13) 0.0408(4) Uani 1 1 d U . .
H1 H 0.4494 0.8059 0.9948 0.049 Uiso 1 1 calc R . .
C11 C 0.1705(2) 0.82175(18) 0.44853(14) 0.0461(4) Uani 1 1 d U . .
H11 H 0.0498 0.8287 0.4005 0.055 Uiso 1 1 calc R . .
C3 C 0.2307(2) 0.53945(18) 0.70720(14) 0.0439(4) Uani 1 1 d U . .
H4 H 0.1728 0.4720 0.6342 0.053 Uiso 1 1 calc R . .
C12 C 0.2503(2) 0.91869(17) 0.56002(14) 0.0432(4) Uani 1 1 d U . .
H12 H 0.1798 0.9894 0.5863 0.052 Uiso 1 1 calc R . .
C10 C 0.2714(2) 0.71546(17) 0.40979(13) 0.0441(4) Uani 1 1 d U . .
H10 H 0.2196 0.6493 0.3353 0.053 Uiso 1 1 calc R . .
H3 H 0.011(3) 0.657(2) 0.694(2) 0.073(6) Uiso 1 1 d . . .
H13 H 0.732(4) 0.957(3) 0.797(2) 0.087(7) Uiso 1 1 d . . .
H8 H 0.985(3) 0.617(2) 1.0935(18) 0.055(5) Uiso 1 1 d . . .
H7 H 1.051(3) 0.777(2) 1.1318(17) 0.061(6) 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
O1 O1 0.000(4) 1 ?
O1 C6 1.2279(17) . ?
O2 C14 1.2416(18) . ?
O3 C14 1.2698(18) . ?
O4 C13 1.289(2) . ?
N2 C6 1.3287(18) . ?
N2 N3 1.4139(16) . ?
N1 C3 1.327(2) . ?
N1 C2 1.337(2) . ?
O5 C13 1.2138(19) . ?
C5 C1 1.380(2) . ?
C5 C4 1.3909(19) . ?
C5 C6 1.5061(19) . ?
C8 C9 1.3990(18) . ?
C8 C7 1.4153(19) . ?
C8 C14 1.514(2) . ?
C6 O1 1.2279(17) 1 ?
C7 C12 1.392(2) . ?
C7 C13 1.5195(18) . ?
C4 C3 1.377(2) . ?
C9 C10 1.376(2) . ?
C2 C1 1.372(2) . ?
C11 C10 1.371(2) . ?
C11 C12 1.385(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
O1 O1 C6 0(10) 1 . ?
C6 N2 N3 120.55(12) . . ?
C3 N1 C2 121.31(13) . . ?
C1 C5 C4 118.79(13) . . ?
C1 C5 C6 124.61(12) . . ?
C4 C5 C6 116.58(13) . . ?
C9 C8 C7 118.02(13) . . ?
C9 C8 C14 113.67(12) . . ?
C7 C8 C14 128.31(12) . . ?
O1 C6 O1 0.00(12) 1 . ?
O1 C6 N2 123.05(13) 1 . ?
O1 C6 N2 123.05(13) . . ?
O1 C6 C5 120.34(12) 1 . ?
O1 C6 C5 120.34(12) . . ?
N2 C6 C5 116.61(12) . . ?
O2 C14 O3 120.91(13) . . ?
O2 C14 C8 118.27(12) . . ?
O3 C14 C8 120.81(13) . . ?
C12 C7 C8 117.92(12) . . ?
C12 C7 C13 113.63(13) . . ?
C8 C7 C13 128.43(14) . . ?
C3 C4 C5 119.26(14) . . ?
C10 C9 C8 122.62(14) . . ?
N1 C2 C1 120.76(14) . . ?
O5 C13 O4 121.13(14) . . ?
O5 C13 C7 118.77(15) . . ?
O4 C13 C7 120.10(14) . . ?
C2 C1 C5 119.29(13) . . ?
C10 C11 C12 119.19(14) . . ?
N1 C3 C4 120.55(13) . . ?
C11 C12 C7 122.75(14) . . ?
C11 C10 C9 119.48(13) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H7 O4 0.92(2) 2.33(2) 3.219(2) 164.1(17) 2_777
N3 H8 O1 0.84(2) 2.276(19) 2.7267(16) 114.1(16) 1
N3 H8 O1 0.84(2) 2.24(2) 2.9602(18) 143.6(17) 2_767
N1 H3 O3 1.00(2) 2.52(2) 3.1702(18) 122.5(16) 1_455
N1 H3 O2 1.00(2) 1.66(2) 2.6591(16) 178.0(19) 1_455
N2 H6 O5 0.86 2.03 2.8016(16) 148.1 2_677

_diffrn_measured_fraction_theta_max 0.965
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.965
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.055
