# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_p
_database_code_depnum_ccdc_archive 'CCDC 1404567'
_audit_update_record             
;
2015-11-01 deposited with the CCDC.
2015-12-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H15 N3 O6'
_chemical_formula_sum            'C18 H15 N3 O6'
_chemical_formula_weight         369.33

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   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.5192(8)
_cell_length_b                   14.4309(10)
_cell_length_c                   10.9492(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.064(2)
_cell_angle_gamma                90.00
_cell_volume                     1786.3(2)
_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       granular
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             772
_exptl_absorpt_coefficient_mu    0.105
_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  'CCD area detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20581
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_sigmaI/netI    0.0250
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.80
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3474
_reflns_number_gt                2883
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WINGX V1.80.03'

_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)+(0.2000P)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         3474
_refine_ls_number_parameters     249
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0474
_refine_ls_wR_factor_ref         0.1945
_refine_ls_wR_factor_gt          0.1708
_refine_ls_goodness_of_fit_ref   0.849
_refine_ls_restrained_S_all      0.849
_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
O2 O 0.73765(9) -0.02976(7) 0.26945(11) 0.0531(4) Uani 1 1 d . . .
O3 O 0.66387(14) 0.04060(13) 0.08826(17) 0.0971(7) Uani 1 1 d . . .
N1 N 0.93039(11) 0.02339(8) 0.36711(10) 0.0401(3) Uani 1 1 d . . .
O4 O 0.98508(11) 0.32778(7) 0.13411(10) 0.0510(3) Uani 1 1 d . . .
O1 O 0.76055(11) 0.12063(8) 0.32919(12) 0.0578(4) Uani 1 1 d . . .
N2 N 0.94250(16) -0.08132(10) 0.07814(13) 0.0629(4) Uani 1 1 d . . .
C1 C 0.81807(13) 0.04253(10) 0.29626(14) 0.0435(4) Uani 1 1 d . . .
C2 C 0.92031(12) 0.05032(9) 0.23322(12) 0.0366(4) Uani 1 1 d . . .
C3 C 0.96897(12) 0.14554(9) 0.20745(12) 0.0352(3) Uani 1 1 d . . .
H3 H 0.9708 0.1483 0.1184 0.042 Uiso 1 1 calc R . .
C11 C 0.5796(2) -0.1036(2) 0.1360(3) 0.1063(10) Uani 1 1 d . . .
H1A H 0.5199 -0.0936 0.0631 0.159 Uiso 1 1 calc R . .
H1B H 0.5429 -0.1115 0.2069 0.159 Uiso 1 1 calc R . .
H1C H 0.6240 -0.1583 0.1249 0.159 Uiso 1 1 calc R . .
C10 C 0.66015(17) -0.02273(14) 0.1562(2) 0.0699(6) Uani 1 1 d . . .
C12 C 1.09559(12) 0.15499(9) 0.27772(12) 0.0365(3) Uani 1 1 d . . .
C17 C 1.11952(14) 0.17849(11) 0.40273(14) 0.0481(4) Uani 1 1 d . . .
H4 H 1.0580 0.1953 0.4422 0.058 Uiso 1 1 calc R . .
C16 C 1.23454(17) 0.17708(14) 0.46922(16) 0.0631(5) Uani 1 1 d . . .
H5 H 1.2511 0.1931 0.5531 0.076 Uiso 1 1 calc R . .
C15 C 1.32394(16) 0.15155(14) 0.40876(19) 0.0641(5) Uani 1 1 d . . .
N3 N 1.44627(19) 0.1484(2) 0.4799(3) 0.1062(8) Uani 1 1 d . . .
O6 O 1.52198(18) 0.1127(3) 0.4309(3) 0.1634(13) Uani 1 1 d . . .
C13 C 1.18856(14) 0.13220(11) 0.21937(15) 0.0481(4) Uani 1 1 d . . .
H9 H 1.1729 0.1179 0.1350 0.058 Uiso 1 1 calc R . .
C14 C 1.30414(16) 0.13038(13) 0.28441(19) 0.0611(5) Uani 1 1 d . . .
H10 H 1.3663 0.1153 0.2450 0.073 Uiso 1 1 calc R . .
O5 O 1.4665(2) 0.1821(3) 0.5828(2) 0.1717(14) Uani 1 1 d . . .
C4 C 0.88440(12) 0.21993(9) 0.23374(12) 0.0375(4) Uani 1 1 d . . .
C6 C 0.90010(13) 0.31229(9) 0.18296(12) 0.0406(4) Uani 1 1 d . . .
C7 C 0.80592(16) 0.38387(11) 0.18786(18) 0.0561(4) Uani 1 1 d . . .
H14A H 0.7430 0.3768 0.1156 0.067 Uiso 1 1 calc R . .
H14B H 0.8396 0.4452 0.1847 0.067 Uiso 1 1 calc R . .
C8 C 0.75483(18) 0.37505(12) 0.3046(2) 0.0655(5) Uani 1 1 d . . .
H15A H 0.6913 0.4196 0.3022 0.079 Uiso 1 1 calc R . .
H15B H 0.8156 0.3887 0.3768 0.079 Uiso 1 1 calc R . .
C9 C 0.70746(15) 0.27748(12) 0.31601(19) 0.0589(5) Uani 1 1 d . . .
H16A H 0.6930 0.2685 0.3996 0.071 Uiso 1 1 calc R . .
H16B H 0.6327 0.2705 0.2584 0.071 Uiso 1 1 calc R . .
C5 C 0.79193(13) 0.20531(10) 0.28911(14) 0.0447(4) Uani 1 1 d . . .
C18 C 0.93231(13) -0.02294(9) 0.14592(12) 0.0420(4) Uani 1 1 d . . .
H1 H 0.9421(16) -0.0351(14) 0.3838(16) 0.052(5) 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
O2 C10 1.386(2) . ?
O2 C1 1.3885(18) . ?
O3 C10 1.184(2) . ?
N1 C1 1.4024(19) . ?
N1 C2 1.4994(16) . ?
N1 H1 0.87(2) . ?
O4 C6 1.2229(19) . ?
O1 C5 1.3702(18) . ?
O1 C1 1.3896(19) . ?
N2 C18 1.144(2) . ?
C1 C2 1.479(2) . ?
C2 C18 1.4495(19) . ?
C2 C3 1.5305(17) . ?
C3 C4 1.5139(19) . ?
C3 C12 1.5190(18) . ?
C3 H3 0.9800 . ?
C11 C10 1.481(3) . ?
C11 H1A 0.9600 . ?
C11 H1B 0.9600 . ?
C11 H1C 0.9600 . ?
C12 C17 1.386(2) . ?
C12 C13 1.388(2) . ?
C17 C16 1.384(2) . ?
C17 H4 0.9300 . ?
C16 C15 1.377(3) . ?
C16 H5 0.9300 . ?
C15 C14 1.371(3) . ?
C15 N3 1.474(3) . ?
N3 O5 1.208(4) . ?
N3 O6 1.222(4) . ?
C13 C14 1.384(2) . ?
C13 H9 0.9300 . ?
C14 H10 0.9300 . ?
C4 C5 1.340(2) . ?
C4 C6 1.4685(19) . ?
C6 C7 1.506(2) . ?
C7 C8 1.512(3) . ?
C7 H14A 0.9700 . ?
C7 H14B 0.9700 . ?
C8 C9 1.524(3) . ?
C8 H15A 0.9700 . ?
C8 H15B 0.9700 . ?
C9 C5 1.493(2) . ?
C9 H16A 0.9700 . ?
C9 H16B 0.9700 . ?

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 O2 C1 115.04(12) . . ?
C1 N1 C2 61.19(9) . . ?
C1 N1 H1 113.4(12) . . ?
C2 N1 H1 116.0(12) . . ?
C5 O1 C1 118.17(12) . . ?
O2 C1 O1 109.40(13) . . ?
O2 C1 N1 118.44(11) . . ?
O1 C1 N1 116.83(13) . . ?
O2 C1 C2 121.14(13) . . ?
O1 C1 C2 121.42(12) . . ?
N1 C1 C2 62.64(9) . . ?
C18 C2 C1 115.93(12) . . ?
C18 C2 N1 117.15(11) . . ?
C1 C2 N1 56.17(9) . . ?
C18 C2 C3 116.66(12) . . ?
C1 C2 C3 120.45(12) . . ?
N1 C2 C3 116.78(10) . . ?
C4 C3 C12 115.50(11) . . ?
C4 C3 C2 109.26(11) . . ?
C12 C3 C2 109.71(10) . . ?
C4 C3 H3 107.3 . . ?
C12 C3 H3 107.3 . . ?
C2 C3 H3 107.3 . . ?
C10 C11 H1A 109.5 . . ?
C10 C11 H1B 109.5 . . ?
H1A C11 H1B 109.5 . . ?
C10 C11 H1C 109.5 . . ?
H1A C11 H1C 109.5 . . ?
H1B C11 H1C 109.5 . . ?
O3 C10 O2 121.59(17) . . ?
O3 C10 C11 127.7(2) . . ?
O2 C10 C11 110.68(16) . . ?
C17 C12 C13 119.22(13) . . ?
C17 C12 C3 120.79(13) . . ?
C13 C12 C3 119.76(12) . . ?
C16 C17 C12 120.32(16) . . ?
C16 C17 H4 119.8 . . ?
C12 C17 H4 119.8 . . ?
C15 C16 C17 118.68(16) . . ?
C15 C16 H5 120.7 . . ?
C17 C16 H5 120.7 . . ?
C14 C15 C16 122.67(16) . . ?
C14 C15 N3 118.5(2) . . ?
C16 C15 N3 118.8(2) . . ?
O5 N3 O6 123.6(2) . . ?
O5 N3 C15 118.3(3) . . ?
O6 N3 C15 118.2(3) . . ?
C14 C13 C12 121.24(15) . . ?
C14 C13 H9 119.4 . . ?
C12 C13 H9 119.4 . . ?
C15 C14 C13 117.83(17) . . ?
C15 C14 H10 121.1 . . ?
C13 C14 H10 121.1 . . ?
C5 C4 C6 118.73(13) . . ?
C5 C4 C3 124.81(12) . . ?
C6 C4 C3 116.17(12) . . ?
O4 C6 C4 119.90(13) . . ?
O4 C6 C7 122.19(13) . . ?
C4 C6 C7 117.84(13) . . ?
C6 C7 C8 111.86(14) . . ?
C6 C7 H14A 109.2 . . ?
C8 C7 H14A 109.2 . . ?
C6 C7 H14B 109.2 . . ?
C8 C7 H14B 109.2 . . ?
H14A C7 H14B 107.9 . . ?
C7 C8 C9 110.52(15) . . ?
C7 C8 H15A 109.5 . . ?
C9 C8 H15A 109.5 . . ?
C7 C8 H15B 109.5 . . ?
C9 C8 H15B 109.5 . . ?
H15A C8 H15B 108.1 . . ?
C5 C9 C8 111.80(14) . . ?
C5 C9 H16A 109.3 . . ?
C8 C9 H16A 109.3 . . ?
C5 C9 H16B 109.3 . . ?
C8 C9 H16B 109.3 . . ?
H16A C9 H16B 107.9 . . ?
C4 C5 O1 124.54(13) . . ?
C4 C5 C9 125.76(14) . . ?
O1 C5 C9 109.70(13) . . ?
N2 C18 C2 179.22(17) . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.069
####################################################################### 
# 
# 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_ardpmhc1_0m
_database_code_depnum_ccdc_archive 'CCDC 1404569'
_audit_update_record             
;
2015-11-01 deposited with the CCDC.
2015-12-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H16 N2 O6'
_chemical_formula_sum            'C22 H16 N2 O6'
_chemical_formula_weight         404.37

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   12.0263(11)
_cell_length_b                   12.8267(12)
_cell_length_c                   15.6641(14)
_cell_angle_alpha                70.463(4)
_cell_angle_beta                 69.253(4)
_cell_angle_gamma                62.293(3)
_cell_volume                     1958.0(3)
_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       granular
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             840
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9819
_exptl_absorpt_correction_T_max  0.9859
_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  'CCD area detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28687
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_sigmaI/netI    0.0298
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.42
_diffrn_reflns_theta_max         27.50
_reflns_number_total             8848
_reflns_number_gt                6057
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WINGX V1.80.03'

_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)+(0.0001P)²+0.8000P] 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         8848
_refine_ls_number_parameters     553
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0675
_refine_ls_R_factor_gt           0.0402
_refine_ls_wR_factor_ref         0.0796
_refine_ls_wR_factor_gt          0.0692
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_restrained_S_all      0.982
_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
C1 C 0.14205(15) -0.08038(14) 0.22169(10) 0.0440(4) Uani 1 1 d . . .
C2 C 0.04004(14) -0.00003(14) 0.17042(10) 0.0433(4) Uani 1 1 d . . .
C3 C 0.05442(14) 0.10638(13) 0.09307(10) 0.0420(3) Uani 1 1 d . . .
H18 H 0.0620 0.0891 0.0344 0.050 Uiso 1 1 calc R . .
C4 C 0.17952(14) 0.11385(13) 0.08525(10) 0.0397(3) Uani 1 1 d . . .
C5 C 0.26857(14) 0.03272(13) 0.13384(10) 0.0388(3) Uani 1 1 d . . .
C6 C -0.03806(15) -0.05203(15) 0.16042(11) 0.0482(4) Uani 1 1 d . . .
C7 C 0.2408(2) -0.40081(17) 0.24788(17) 0.0905(7) Uani 1 1 d . . .
H25 H 0.2775 -0.4524 0.2041 0.136 Uiso 1 1 calc R . .
H24 H 0.1590 -0.4035 0.2852 0.136 Uiso 1 1 calc R . .
H23 H 0.2983 -0.4275 0.2875 0.136 Uiso 1 1 calc R . .
C8 C 0.38825(14) 0.04317(13) 0.12103(10) 0.0390(3) Uani 1 1 d . . .
C9 C 0.40877(14) 0.14037(13) 0.05556(10) 0.0428(3) Uani 1 1 d . . .
C10 C 0.51892(16) 0.16049(16) 0.03865(12) 0.0557(4) Uani 1 1 d . . .
H19 H 0.5302 0.2273 -0.0045 0.067 Uiso 1 1 calc R . .
C11 C 0.61119(16) 0.07945(17) 0.08713(13) 0.0588(5) Uani 1 1 d . . .
H20 H 0.6862 0.0912 0.0762 0.071 Uiso 1 1 calc R . .
C12 C 0.59421(16) -0.01926(16) 0.15183(12) 0.0547(4) Uani 1 1 d . . .
H21 H 0.6581 -0.0737 0.1836 0.066 Uiso 1 1 calc R . .
C13 C 0.48332(15) -0.03769(14) 0.16969(11) 0.0473(4) Uani 1 1 d . . .
H22 H 0.4718 -0.1037 0.2140 0.057 Uiso 1 1 calc R . .
C14 C 0.20841(15) 0.20986(14) 0.01307(11) 0.0457(4) Uani 1 1 d . . .
C15 C -0.06460(14) 0.22133(14) 0.10668(11) 0.0438(4) Uani 1 1 d . . .
C16 C -0.15925(15) 0.26028(15) 0.05889(11) 0.0507(4) Uani 1 1 d . . .
H26 H -0.1491 0.2151 0.0189 0.061 Uiso 1 1 calc R . .
C17 C -0.26814(16) 0.36489(15) 0.06981(12) 0.0547(4) Uani 1 1 d . . .
H27 H -0.3310 0.3891 0.0378 0.066 Uiso 1 1 calc R . .
C18 C -0.28415(16) 0.43381(15) 0.12819(12) 0.0521(4) Uani 1 1 d . . .
C19 C -0.08271(16) 0.29014(15) 0.16570(12) 0.0504(4) Uani 1 1 d . . .
H29 H -0.0209 0.2649 0.1989 0.060 Uiso 1 1 calc R . .
C20 C -0.19111(16) 0.39611(15) 0.17656(12) 0.0541(4) Uani 1 1 d . . .
H28 H -0.2011 0.4416 0.2162 0.065 Uiso 1 1 calc R . .
C21 C -0.4112(2) 0.61174(17) 0.19021(14) 0.0731(6) Uani 1 1 d . . .
H32 H -0.4122 0.5680 0.2534 0.110 Uiso 1 1 calc R . .
H31 H -0.4914 0.6807 0.1883 0.110 Uiso 1 1 calc R . .
H30 H -0.3408 0.6377 0.1666 0.110 Uiso 1 1 calc R . .
C22 C 0.44900(16) 0.78533(15) 0.46024(11) 0.0495(4) Uani 1 1 d . . .
C23 C 0.57344(17) 0.68539(15) 0.47252(11) 0.0498(4) Uani 1 1 d . . .
C24 C 0.69371(16) 0.70781(14) 0.45668(11) 0.0488(4) Uani 1 1 d . . .
H2 H 0.7139 0.6861 0.5173 0.059 Uiso 1 1 calc R . .
C25 C 0.66369(15) 0.84068(14) 0.41925(10) 0.0460(4) Uani 1 1 d . . .
C26 C 0.54621(15) 0.92524(15) 0.40934(10) 0.0457(4) Uani 1 1 d . . .
C27 C 0.76782(17) 0.87918(16) 0.40026(12) 0.0525(4) Uani 1 1 d . . .
C28 C 0.52477(15) 1.04944(14) 0.36665(10) 0.0455(4) Uani 1 1 d . . .
C29 C 0.62974(16) 1.08092(15) 0.34005(11) 0.0494(4) Uani 1 1 d . . .
C30 C 0.62182(19) 1.19561(16) 0.29376(13) 0.0618(5) Uani 1 1 d . . .
H3 H 0.6932 1.2152 0.2768 0.074 Uiso 1 1 calc R . .
C31 C 0.5070(2) 1.27994(17) 0.27329(14) 0.0699(5) Uani 1 1 d . . .
H6 H 0.5006 1.3575 0.2420 0.084 Uiso 1 1 calc R . .
C32 C 0.39996(19) 1.25162(17) 0.29841(13) 0.0657(5) Uani 1 1 d . . .
H4 H 0.3226 1.3098 0.2838 0.079 Uiso 1 1 calc R . .
C33 C 0.40849(17) 1.13706(15) 0.34500(12) 0.0549(4) Uani 1 1 d . . .
H5 H 0.3367 1.1180 0.3621 0.066 Uiso 1 1 calc R . .
C34 C 0.57064(18) 0.57375(17) 0.53651(12) 0.0570(4) Uani 1 1 d . . .
C35 C 0.1178(2) 0.8039(2) 0.55205(17) 0.0958(8) Uani 1 1 d . . .
H9 H 0.0878 0.8522 0.5974 0.144 Uiso 1 1 calc R . .
H7 H 0.1426 0.7206 0.5824 0.144 Uiso 1 1 calc R . .
H8 H 0.0498 0.8269 0.5225 0.144 Uiso 1 1 calc R . .
C36 C 0.80765(16) 0.62714(14) 0.39446(11) 0.0473(4) Uani 1 1 d . . .
C37 C 0.82626(17) 0.65855(15) 0.29858(11) 0.0556(4) Uani 1 1 d . . .
H10 H 0.7691 0.7316 0.2721 0.067 Uiso 1 1 calc R . .
C38 C 0.92652(17) 0.58532(16) 0.24092(12) 0.0574(4) Uani 1 1 d . . .
H11 H 0.9369 0.6089 0.1766 0.069 Uiso 1 1 calc R . .
C39 C 1.01106(16) 0.47701(15) 0.27943(13) 0.0550(4) Uani 1 1 d . . .
C40 C 0.99436(17) 0.44265(16) 0.37549(13) 0.0608(5) Uani 1 1 d . . .
H13 H 1.0511 0.3692 0.4018 0.073 Uiso 1 1 calc R . .
C41 C 0.89366(17) 0.51747(15) 0.43187(12) 0.0559(4) Uani 1 1 d . . .
H12 H 0.8832 0.4939 0.4962 0.067 Uiso 1 1 calc R . .
C42 C 1.1435(2) 0.4395(2) 0.12893(17) 0.0968(8) Uani 1 1 d . . .
H16 H 1.0756 0.4482 0.1052 0.145 Uiso 1 1 calc R . .
H14 H 1.2240 0.3820 0.1013 0.145 Uiso 1 1 calc R . .
H15 H 1.1500 0.5158 0.1139 0.145 Uiso 1 1 calc R . .
C43 C 0.22174(16) -0.27544(15) 0.19660(14) 0.0532(4) Uani 1 1 d . . .
C44 C 0.23079(19) 0.82252(19) 0.48070(14) 0.0677(5) Uani 1 1 d . . .
H1 H 0.4913(18) 0.6658(17) 0.3890(13) 0.078(6) Uiso 1 1 d . . .
H17 H -0.0187(17) -0.0273(15) 0.3069(12) 0.059(5) Uiso 1 1 d . . .
N1 N 0.03107(14) 0.00631(13) 0.26673(10) 0.0521(4) Uani 1 1 d . . .
N2 N -0.09908(15) -0.09116(15) 0.15069(12) 0.0688(4) Uani 1 1 d . . .
N3 N 0.52263(14) 0.72021(13) 0.38772(9) 0.0532(4) Uani 1 1 d . . .
N4 N 0.57283(18) 0.48356(15) 0.58339(11) 0.0756(5) Uani 1 1 d . . .
O1 O 0.25873(10) -0.06730(9) 0.19750(7) 0.0473(3) Uani 1 1 d . . .
O2 O 0.32028(10) 0.22183(10) 0.00379(7) 0.0515(3) Uani 1 1 d . . .
O3 O 0.14219(12) 0.28104(11) -0.03999(8) 0.0663(3) Uani 1 1 d . . .
O4 O -0.39538(12) 0.53602(11) 0.13434(10) 0.0687(4) Uani 1 1 d . . .
O5 O 0.16359(11) -0.20067(10) 0.25944(7) 0.0512(3) Uani 1 1 d . . .
O6 O 0.24940(12) -0.23939(11) 0.11486(9) 0.0656(3) Uani 1 1 d . . .
O7 O 1.11517(13) 0.39882(12) 0.22791(11) 0.0780(4) Uani 1 1 d . . .
O8 O 0.74659(11) 0.99817(10) 0.35971(8) 0.0566(3) Uani 1 1 d . . .
O9 O 0.87136(12) 0.81674(12) 0.41862(10) 0.0720(4) Uani 1 1 d . . .
O10 O 0.43547(10) 0.90474(10) 0.43820(8) 0.0530(3) Uani 1 1 d . . .
O11 O 0.33599(11) 0.77554(11) 0.51959(7) 0.0571(3) Uani 1 1 d . . .
O12 O 0.23773(16) 0.86882(18) 0.40154(11) 0.1092(6) 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
C1 O5 1.3871(18) . ?
C1 O1 1.3930(17) . ?
C1 N1 1.412(2) . ?
C1 C2 1.477(2) . ?
C2 C6 1.452(2) . ?
C2 N1 1.501(2) . ?
C2 C3 1.525(2) . ?
C3 C4 1.511(2) . ?
C3 C15 1.516(2) . ?
C3 H18 0.9800 . ?
C4 C5 1.3493(19) . ?
C4 C14 1.450(2) . ?
C5 O1 1.3624(16) . ?
C5 C8 1.4445(19) . ?
C6 N2 1.134(2) . ?
C7 C43 1.486(2) . ?
C7 H25 0.9600 . ?
C7 H24 0.9600 . ?
C7 H23 0.9600 . ?
C8 C9 1.385(2) . ?
C8 C13 1.396(2) . ?
C9 O2 1.3758(17) . ?
C9 C10 1.384(2) . ?
C10 C11 1.373(2) . ?
C10 H19 0.9300 . ?
C11 C12 1.381(2) . ?
C11 H20 0.9300 . ?
C12 C13 1.377(2) . ?
C12 H21 0.9300 . ?
C13 H22 0.9300 . ?
C14 O3 1.2016(18) . ?
C14 O2 1.3759(18) . ?
C15 C19 1.380(2) . ?
C15 C16 1.389(2) . ?
C16 C17 1.380(2) . ?
C16 H26 0.9300 . ?
C17 C18 1.383(2) . ?
C17 H27 0.9300 . ?
C18 O4 1.3710(19) . ?
C18 C20 1.383(2) . ?
C19 C20 1.388(2) . ?
C19 H29 0.9300 . ?
C20 H28 0.9300 . ?
C21 O4 1.423(2) . ?
C21 H32 0.9600 . ?
C21 H31 0.9600 . ?
C21 H30 0.9600 . ?
C22 O11 1.3831(18) . ?
C22 O10 1.3951(19) . ?
C22 N3 1.416(2) . ?
C22 C23 1.475(2) . ?
C23 C34 1.455(2) . ?
C23 N3 1.504(2) . ?
C23 C24 1.524(2) . ?
C24 C25 1.513(2) . ?
C24 C36 1.519(2) . ?
C24 H2 0.9800 . ?
C25 C26 1.347(2) . ?
C25 C27 1.454(2) . ?
C26 O10 1.3663(18) . ?
C26 C28 1.442(2) . ?
C27 O9 1.203(2) . ?
C27 O8 1.379(2) . ?
C28 C29 1.385(2) . ?
C28 C33 1.398(2) . ?
C29 O8 1.3773(19) . ?
C29 C30 1.380(2) . ?
C30 C31 1.368(3) . ?
C30 H3 0.9300 . ?
C31 C32 1.387(3) . ?
C31 H6 0.9300 . ?
C32 C33 1.378(2) . ?
C32 H4 0.9300 . ?
C33 H5 0.9300 . ?
C34 N4 1.138(2) . ?
C35 C44 1.484(3) . ?
C35 H9 0.9600 . ?
C35 H7 0.9600 . ?
C35 H8 0.9600 . ?
C36 C37 1.382(2) . ?
C36 C41 1.385(2) . ?
C37 C38 1.376(2) . ?
C37 H10 0.9300 . ?
C38 C39 1.374(2) . ?
C38 H11 0.9300 . ?
C39 O7 1.372(2) . ?
C39 C40 1.387(2) . ?
C40 C41 1.377(2) . ?
C40 H13 0.9300 . ?
C41 H12 0.9300 . ?
C42 O7 1.429(3) . ?
C42 H16 0.9600 . ?
C42 H14 0.9600 . ?
C42 H15 0.9600 . ?
C43 O6 1.187(2) . ?
C43 O5 1.378(2) . ?
C44 O12 1.174(2) . ?
C44 O11 1.388(2) . ?
N1 H17 0.855(17) . ?
N3 H1 0.93(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
O5 C1 O1 108.65(12) . . ?
O5 C1 N1 117.75(13) . . ?
O1 C1 N1 117.35(13) . . ?
O5 C1 C2 122.19(13) . . ?
O1 C1 C2 121.59(12) . . ?
N1 C1 C2 62.57(10) . . ?
C6 C2 C1 117.24(13) . . ?
C6 C2 N1 118.15(13) . . ?
C1 C2 N1 56.60(10) . . ?
C6 C2 C3 115.12(13) . . ?
C1 C2 C3 121.16(12) . . ?
N1 C2 C3 115.99(13) . . ?
C4 C3 C15 114.45(12) . . ?
C4 C3 C2 109.09(12) . . ?
C15 C3 C2 111.41(12) . . ?
C4 C3 H18 107.2 . . ?
C15 C3 H18 107.2 . . ?
C2 C3 H18 107.2 . . ?
C5 C4 C14 119.15(13) . . ?
C5 C4 C3 124.82(13) . . ?
C14 C4 C3 115.74(13) . . ?
C4 C5 O1 125.16(13) . . ?
C4 C5 C8 122.09(13) . . ?
O1 C5 C8 112.74(12) . . ?
N2 C6 C2 178.49(18) . . ?
C43 C7 H25 109.5 . . ?
C43 C7 H24 109.5 . . ?
H25 C7 H24 109.5 . . ?
C43 C7 H23 109.5 . . ?
H25 C7 H23 109.5 . . ?
H24 C7 H23 109.5 . . ?
C9 C8 C13 118.54(14) . . ?
C9 C8 C5 116.98(13) . . ?
C13 C8 C5 124.49(13) . . ?
O2 C9 C10 116.61(14) . . ?
O2 C9 C8 121.44(13) . . ?
C10 C9 C8 121.95(14) . . ?
C11 C10 C9 118.39(16) . . ?
C11 C10 H19 120.8 . . ?
C9 C10 H19 120.8 . . ?
C10 C11 C12 120.91(15) . . ?
C10 C11 H20 119.5 . . ?
C12 C11 H20 119.5 . . ?
C13 C12 C11 120.48(16) . . ?
C13 C12 H21 119.8 . . ?
C11 C12 H21 119.8 . . ?
C12 C13 C8 119.71(15) . . ?
C12 C13 H22 120.1 . . ?
C8 C13 H22 120.1 . . ?
O3 C14 O2 116.52(14) . . ?
O3 C14 C4 125.34(15) . . ?
O2 C14 C4 118.15(13) . . ?
C19 C15 C16 118.07(15) . . ?
C19 C15 C3 121.92(13) . . ?
C16 C15 C3 120.01(14) . . ?
C17 C16 C15 121.06(16) . . ?
C17 C16 H26 119.5 . . ?
C15 C16 H26 119.5 . . ?
C16 C17 C18 120.24(15) . . ?
C16 C17 H27 119.9 . . ?
C18 C17 H27 119.9 . . ?
O4 C18 C20 124.70(16) . . ?
O4 C18 C17 115.86(15) . . ?
C20 C18 C17 119.44(16) . . ?
C15 C19 C20 121.42(15) . . ?
C15 C19 H29 119.3 . . ?
C20 C19 H29 119.3 . . ?
C18 C20 C19 119.76(16) . . ?
C18 C20 H28 120.1 . . ?
C19 C20 H28 120.1 . . ?
O4 C21 H32 109.5 . . ?
O4 C21 H31 109.5 . . ?
H32 C21 H31 109.5 . . ?
O4 C21 H30 109.5 . . ?
H32 C21 H30 109.5 . . ?
H31 C21 H30 109.5 . . ?
O11 C22 O10 109.60(14) . . ?
O11 C22 N3 122.49(14) . . ?
O10 C22 N3 115.99(13) . . ?
O11 C22 C23 118.65(13) . . ?
O10 C22 C23 120.95(14) . . ?
N3 C22 C23 62.65(11) . . ?
C34 C23 C22 118.04(15) . . ?
C34 C23 N3 116.19(14) . . ?
C22 C23 N3 56.77(10) . . ?
C34 C23 C24 115.24(14) . . ?
C22 C23 C24 121.62(14) . . ?
N3 C23 C24 115.84(13) . . ?
C25 C24 C36 114.14(13) . . ?
C25 C24 C23 108.86(13) . . ?
C36 C24 C23 109.85(13) . . ?
C25 C24 H2 107.9 . . ?
C36 C24 H2 107.9 . . ?
C23 C24 H2 107.9 . . ?
C26 C25 C27 118.48(15) . . ?
C26 C25 C24 124.71(14) . . ?
C27 C25 C24 116.61(14) . . ?
C25 C26 O10 124.86(14) . . ?
C25 C26 C28 122.48(14) . . ?
O10 C26 C28 112.66(14) . . ?
O9 C27 O8 116.24(15) . . ?
O9 C27 C25 125.74(17) . . ?
O8 C27 C25 118.00(15) . . ?
C29 C28 C33 118.40(15) . . ?
C29 C28 C26 117.09(15) . . ?
C33 C28 C26 124.36(15) . . ?
O8 C29 C30 117.34(15) . . ?
O8 C29 C28 120.82(14) . . ?
C30 C29 C28 121.83(17) . . ?
C31 C30 C29 118.76(17) . . ?
C31 C30 H3 120.6 . . ?
C29 C30 H3 120.6 . . ?
C30 C31 C32 121.06(18) . . ?
C30 C31 H6 119.5 . . ?
C32 C31 H6 119.5 . . ?
C33 C32 C31 119.83(18) . . ?
C33 C32 H4 120.1 . . ?
C31 C32 H4 120.1 . . ?
C32 C33 C28 120.12(17) . . ?
C32 C33 H5 119.9 . . ?
C28 C33 H5 119.9 . . ?
N4 C34 C23 176.8(2) . . ?
C44 C35 H9 109.5 . . ?
C44 C35 H7 109.5 . . ?
H9 C35 H7 109.5 . . ?
C44 C35 H8 109.5 . . ?
H9 C35 H8 109.5 . . ?
H7 C35 H8 109.5 . . ?
C37 C36 C41 117.60(16) . . ?
C37 C36 C24 121.11(14) . . ?
C41 C36 C24 121.24(14) . . ?
C38 C37 C36 122.19(16) . . ?
C38 C37 H10 118.9 . . ?
C36 C37 H10 118.9 . . ?
C39 C38 C37 119.30(16) . . ?
C39 C38 H11 120.4 . . ?
C37 C38 H11 120.4 . . ?
O7 C39 C38 123.70(17) . . ?
O7 C39 C40 116.45(16) . . ?
C38 C39 C40 119.84(17) . . ?
C41 C40 C39 119.90(16) . . ?
C41 C40 H13 120.0 . . ?
C39 C40 H13 120.0 . . ?
C40 C41 C36 121.16(16) . . ?
C40 C41 H12 119.4 . . ?
C36 C41 H12 119.4 . . ?
O7 C42 H16 109.5 . . ?
O7 C42 H14 109.5 . . ?
H16 C42 H14 109.5 . . ?
O7 C42 H15 109.5 . . ?
H16 C42 H15 109.5 . . ?
H14 C42 H15 109.5 . . ?
O6 C43 O5 122.43(16) . . ?
O6 C43 C7 128.24(19) . . ?
O5 C43 C7 109.33(17) . . ?
O12 C44 O11 121.40(18) . . ?
O12 C44 C35 128.1(2) . . ?
O11 C44 C35 110.49(17) . . ?
C1 N1 C2 60.83(10) . . ?
C1 N1 H17 109.7(12) . . ?
C2 N1 H17 109.7(12) . . ?
C22 N3 C23 60.58(11) . . ?
C22 N3 H1 112.5(12) . . ?
C23 N3 H1 110.9(12) . . ?
C5 O1 C1 117.47(11) . . ?
C9 O2 C14 121.89(12) . . ?
C18 O4 C21 117.02(15) . . ?
C43 O5 C1 115.94(12) . . ?
C39 O7 C42 117.10(16) . . ?
C29 O8 C27 122.21(13) . . ?
C26 O10 C22 117.22(13) . . ?
C22 O11 C44 116.62(13) . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.175
_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_isohc_0m
_database_code_depnum_ccdc_archive 'CCDC 1404581'
_audit_update_record             
;
2015-11-01 deposited with the CCDC.
2015-12-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H16 N2 O5'
_chemical_formula_sum            'C18 H16 N2 O5'
_chemical_formula_weight         340.33

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

_cell_length_a                   8.1462(19)
_cell_length_b                   9.013(2)
_cell_length_c                   12.122(3)
_cell_angle_alpha                76.794(10)
_cell_angle_beta                 72.910(9)
_cell_angle_gamma                79.128(9)
_cell_volume                     821.2(3)
_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       granular
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             358
_exptl_absorpt_coefficient_mu    0.102
_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  'CCD area detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8736
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_av_sigmaI/netI    0.0275
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.79
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3181
_reflns_number_gt                2741
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WINGX V1.80.03'

_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)+(0.1993P)²+0.2536P] 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         3181
_refine_ls_number_parameters     233
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0452
_refine_ls_wR_factor_ref         0.1725
_refine_ls_wR_factor_gt          0.1557
_refine_ls_goodness_of_fit_ref   0.677
_refine_ls_restrained_S_all      0.677
_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 0.57652(17) 0.78420(16) 0.47796(12) 0.0635(4) Uani 1 1 d . . .
O2 O 0.84220(13) 0.76234(13) 0.35503(10) 0.0440(3) Uani 1 1 d . . .
O1 O 0.67190(14) 0.81035(12) 0.22967(10) 0.0426(3) Uani 1 1 d . . .
O4 O 0.22415(13) 0.72891(12) 0.17712(10) 0.0431(3) Uani 1 1 d . . .
O5 O 0.26490(14) 0.48354(13) 0.24892(11) 0.0499(3) Uani 1 1 d . . .
C5 C 0.52687(17) 0.77107(16) 0.21598(12) 0.0328(3) Uani 1 1 d . . .
C6 C 0.41657(18) 0.90294(16) 0.17172(12) 0.0354(3) Uani 1 1 d . . .
C13 C 0.7237(2) 0.80507(18) 0.45388(15) 0.0477(4) Uani 1 1 d . . .
C1 C 0.77618(17) 0.69670(17) 0.28686(13) 0.0378(3) Uani 1 1 d . . .
C9 C 0.4532(2) 1.05418(17) 0.14622(14) 0.0464(4) Uani 1 1 d . . .
H3 H 0.5528 1.0754 0.1591 0.056 Uiso 1 1 calc R . .
C10 C 0.3421(3) 1.1720(2) 0.10209(17) 0.0571(5) Uani 1 1 d . . .
H4 H 0.3661 1.2727 0.0861 0.069 Uiso 1 1 calc R . .
C11 C 0.1946(2) 1.1410(2) 0.08133(17) 0.0587(5) Uani 1 1 d . . .
H5 H 0.1213 1.2211 0.0502 0.070 Uiso 1 1 calc R . .
C7 C 0.26719(18) 0.87487(17) 0.15235(13) 0.0383(4) Uani 1 1 d . . .
C8 C 0.32341(17) 0.60399(16) 0.22479(13) 0.0363(3) Uani 1 1 d . . .
C4 C 0.48683(16) 0.62666(15) 0.23968(12) 0.0324(3) Uani 1 1 d . . .
C3 C 0.59254(16) 0.48582(15) 0.29076(12) 0.0337(3) Uani 1 1 d . . .
H9 H 0.5167 0.4431 0.3660 0.040 Uiso 1 1 calc R . .
C15 C 0.64822(19) 0.35539(17) 0.21758(14) 0.0427(4) Uani 1 1 d . . .
H10 H 0.5424 0.3139 0.2237 0.051 Uiso 1 1 calc R . .
C17 C 0.7655(2) 0.2238(2) 0.27089(18) 0.0572(5) Uani 1 1 d . . .
H11A H 0.7851 0.1388 0.2311 0.086 Uiso 1 1 calc R . .
H11B H 0.7110 0.1920 0.3527 0.086 Uiso 1 1 calc R . .
H11C H 0.8742 0.2575 0.2625 0.086 Uiso 1 1 calc R . .
C16 C 0.7280(3) 0.4081(2) 0.08750(16) 0.0591(5) Uani 1 1 d . . .
H12A H 0.8316 0.4515 0.0772 0.089 Uiso 1 1 calc R . .
H12B H 0.6470 0.4843 0.0549 0.089 Uiso 1 1 calc R . .
H12C H 0.7558 0.3218 0.0482 0.089 Uiso 1 1 calc R . .
C2 C 0.74151(17) 0.53470(16) 0.32035(12) 0.0359(3) Uani 1 1 d . . .
C14 C 0.8067(3) 0.8727(2) 0.52150(19) 0.0699(6) Uani 1 1 d . . .
H14A H 0.7301 0.9583 0.5505 0.105 Uiso 1 1 calc R . .
H14B H 0.9130 0.9071 0.4713 0.105 Uiso 1 1 calc R . .
H14C H 0.8306 0.7965 0.5864 0.105 Uiso 1 1 calc R . .
N1 N 0.88816(16) 0.59130(16) 0.22007(12) 0.0433(3) Uani 1 1 d . . .
C18 C 0.78312(19) 0.44867(18) 0.42779(14) 0.0448(4) Uani 1 1 d . . .
N2 N 0.8143(2) 0.3798(2) 0.51203(14) 0.0667(5) Uani 1 1 d . . .
C12 C 0.1557(2) 0.9923(2) 0.10650(16) 0.0534(4) Uani 1 1 d . . .
H18 H 0.0566 0.9713 0.0929 0.064 Uiso 1 1 calc R . .
H H 0.986(3) 0.567(3) 0.2402(19) 0.065(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
O3 C13 1.189(2) . ?
O2 C13 1.381(2) . ?
O2 C1 1.3880(17) . ?
O1 C5 1.3596(16) . ?
O1 C1 1.3946(17) . ?
O4 C7 1.3695(19) . ?
O4 C8 1.3746(17) . ?
O5 C8 1.2081(18) . ?
C5 C4 1.348(2) . ?
C5 C6 1.4481(19) . ?
C6 C7 1.382(2) . ?
C6 C9 1.396(2) . ?
C13 C14 1.487(2) . ?
C1 N1 1.407(2) . ?
C1 C2 1.481(2) . ?
C9 C10 1.377(2) . ?
C9 H3 0.9300 . ?
C10 C11 1.386(3) . ?
C10 H4 0.9300 . ?
C11 C12 1.381(3) . ?
C11 H5 0.9300 . ?
C7 C12 1.385(2) . ?
C8 C4 1.4517(18) . ?
C4 C3 1.5094(18) . ?
C3 C2 1.5249(18) . ?
C3 C15 1.5536(19) . ?
C3 H9 0.9800 . ?
C15 C16 1.519(3) . ?
C15 C17 1.524(2) . ?
C15 H10 0.9800 . ?
C17 H11A 0.9600 . ?
C17 H11B 0.9600 . ?
C17 H11C 0.9600 . ?
C16 H12A 0.9600 . ?
C16 H12B 0.9600 . ?
C16 H12C 0.9600 . ?
C2 C18 1.453(2) . ?
C2 N1 1.5027(19) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
N1 H 0.87(2) . ?
C18 N2 1.138(2) . ?
C12 H18 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
C13 O2 C1 115.34(12) . . ?
C5 O1 C1 117.78(11) . . ?
C7 O4 C8 122.30(11) . . ?
C4 C5 O1 125.05(12) . . ?
C4 C5 C6 122.45(13) . . ?
O1 C5 C6 112.50(12) . . ?
C7 C6 C9 118.74(14) . . ?
C7 C6 C5 117.03(13) . . ?
C9 C6 C5 124.22(14) . . ?
O3 C13 O2 121.22(15) . . ?
O3 C13 C14 127.40(18) . . ?
O2 C13 C14 111.36(15) . . ?
O2 C1 O1 109.02(12) . . ?
O2 C1 N1 118.44(12) . . ?
O1 C1 N1 116.67(13) . . ?
O2 C1 C2 121.86(12) . . ?
O1 C1 C2 121.37(11) . . ?
N1 C1 C2 62.63(10) . . ?
C10 C9 C6 120.06(16) . . ?
C10 C9 H3 120.0 . . ?
C6 C9 H3 120.0 . . ?
C9 C10 C11 120.28(17) . . ?
C9 C10 H4 119.9 . . ?
C11 C10 H4 119.9 . . ?
C12 C11 C10 120.49(15) . . ?
C12 C11 H5 119.8 . . ?
C10 C11 H5 119.8 . . ?
O4 C7 C6 121.09(13) . . ?
O4 C7 C12 117.25(14) . . ?
C6 C7 C12 121.66(15) . . ?
O5 C8 O4 115.37(12) . . ?
O5 C8 C4 126.23(13) . . ?
O4 C8 C4 118.39(12) . . ?
C5 C4 C8 118.47(12) . . ?
C5 C4 C3 124.83(12) . . ?
C8 C4 C3 116.50(11) . . ?
C4 C3 C2 109.25(11) . . ?
C4 C3 C15 114.79(12) . . ?
C2 C3 C15 114.21(11) . . ?
C4 C3 H9 105.9 . . ?
C2 C3 H9 105.9 . . ?
C15 C3 H9 105.9 . . ?
C16 C15 C17 111.37(14) . . ?
C16 C15 C3 114.52(13) . . ?
C17 C15 C3 110.92(13) . . ?
C16 C15 H10 106.5 . . ?
C17 C15 H10 106.5 . . ?
C3 C15 H10 106.5 . . ?
C15 C17 H11A 109.5 . . ?
C15 C17 H11B 109.5 . . ?
H11A C17 H11B 109.5 . . ?
C15 C17 H11C 109.5 . . ?
H11A C17 H11C 109.5 . . ?
H11B C17 H11C 109.5 . . ?
C15 C16 H12A 109.5 . . ?
C15 C16 H12B 109.5 . . ?
H12A C16 H12B 109.5 . . ?
C15 C16 H12C 109.5 . . ?
H12A C16 H12C 109.5 . . ?
H12B C16 H12C 109.5 . . ?
C18 C2 C1 115.87(12) . . ?
C18 C2 N1 117.63(12) . . ?
C1 C2 N1 56.27(9) . . ?
C18 C2 C3 115.54(12) . . ?
C1 C2 C3 120.96(11) . . ?
N1 C2 C3 117.73(12) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C1 N1 C2 61.09(10) . . ?
C1 N1 H 109.9(15) . . ?
C2 N1 H 110.5(14) . . ?
N2 C18 C2 179.05(19) . . ?
C11 C12 C7 118.75(17) . . ?
C11 C12 H18 120.6 . . ?
C7 C12 H18 120.6 . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.063
####################################################################### 
# 
# 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_paaaz
_database_code_depnum_ccdc_archive 'CCDC 1434523'
_audit_update_record             
;
2015-11-01 deposited with the CCDC.
2015-12-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H19 N3 O6'
_chemical_formula_sum            'C24 H19 N3 O6'
_chemical_formula_weight         445.42

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

_cell_length_a                   7.8756(12)
_cell_length_b                   12.1142(18)
_cell_length_c                   12.4328(19)
_cell_angle_alpha                86.913(7)
_cell_angle_beta                 76.478(7)
_cell_angle_gamma                73.204(7)
_cell_volume                     1104.0(3)
_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       granular
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             466
_exptl_absorpt_coefficient_mu    0.098
_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  'CCD area detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11956
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_av_sigmaI/netI    0.0272
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.68
_diffrn_reflns_theta_max         26.00
_reflns_number_total             4287
_reflns_number_gt                3507
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WINGX V1.80.03'

_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)+(0.2000P)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         4287
_refine_ls_number_parameters     302
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0515
_refine_ls_wR_factor_ref         0.2208
_refine_ls_wR_factor_gt          0.1965
_refine_ls_goodness_of_fit_ref   0.947
_refine_ls_restrained_S_all      0.947
_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
O2 O 0.10484(16) 0.18085(12) 0.30728(10) 0.0519(4) Uani 1 1 d . . .
O6 O 0.7999(4) -0.50771(17) 0.03026(18) 0.1069(7) Uani 1 1 d . . .
N1 N 0.3020(2) 0.01227(14) 0.20597(12) 0.0466(4) Uani 1 1 d . . .
O4 O 0.95319(15) -0.02788(11) 0.21693(11) 0.0508(4) Uani 1 1 d . . .
O1 O 0.36542(16) 0.19462(11) 0.19140(10) 0.0494(4) Uani 1 1 d . . .
O3 O 0.2108(2) 0.24402(14) 0.43756(13) 0.0709(5) Uani 1 1 d . . .
C1 C 0.2802(2) 0.11887(16) 0.25467(14) 0.0441(4) Uani 1 1 d . . .
C3 C 0.5914(2) -0.02028(14) 0.27571(12) 0.0385(4) Uani 1 1 d . . .
H2 H 0.6299 -0.0185 0.3449 0.046 Uiso 1 1 calc R . .
C18 C 0.6631(2) -0.14359(14) 0.23198(13) 0.0389(4) Uani 1 1 d . . .
C11 C -0.2868(6) 0.4320(4) 0.7734(3) 0.1144(12) Uani 1 1 d . . .
H13 H -0.3250 0.4579 0.8466 0.137 Uiso 1 1 calc R . .
C12 C -0.2968(7) 0.5079(3) 0.6886(3) 0.1468(19) Uani 1 1 d . . .
H14 H -0.3450 0.5865 0.7041 0.176 Uiso 1 1 calc R . .
C13 C -0.2361(6) 0.4694(3) 0.5799(3) 0.1330(18) Uani 1 1 d . . .
H15 H -0.2421 0.5225 0.5230 0.160 Uiso 1 1 calc R . .
C8 C -0.1678(3) 0.3548(2) 0.55515(17) 0.0679(6) Uani 1 1 d . . .
C7 C -0.1125(3) 0.3097(2) 0.43816(18) 0.0730(7) Uani 1 1 d . . .
H9 H -0.1413 0.3742 0.3894 0.088 Uiso 1 1 calc R . .
H10 H -0.1850 0.2591 0.4311 0.088 Uiso 1 1 calc R . .
C6 C 0.0853(3) 0.24513(16) 0.39990(15) 0.0548(5) Uani 1 1 d . . .
C2 C 0.3844(2) 0.01386(15) 0.30296(13) 0.0418(4) Uani 1 1 d . . .
C23 C 0.7011(3) -0.23293(18) 0.30486(16) 0.0617(6) Uani 1 1 d . . .
H19 H 0.6910 -0.2166 0.3787 0.074 Uiso 1 1 calc R . .
C22 C 0.7538(4) -0.3459(2) 0.26858(19) 0.0777(7) Uani 1 1 d . . .
H18 H 0.7789 -0.4059 0.3177 0.093 Uiso 1 1 calc R . .
C21 C 0.7690(3) -0.36907(16) 0.15958(17) 0.0578(5) Uani 1 1 d . . .
N3 N 0.8174(4) -0.48921(17) 0.12148(19) 0.0830(6) Uani 1 1 d . . .
C9 C -0.1581(5) 0.2803(2) 0.6412(2) 0.0860(8) Uani 1 1 d . . .
H11 H -0.1080 0.2017 0.6262 0.103 Uiso 1 1 calc R . .
C10 C -0.2199(6) 0.3179(3) 0.7486(2) 0.1092(11) Uani 1 1 d . . .
H12 H -0.2160 0.2646 0.8054 0.131 Uiso 1 1 calc R . .
O5 O 0.8691(5) -0.56548(17) 0.1828(2) 0.1299(10) Uani 1 1 d . . .
C20 C 0.7362(3) -0.28243(16) 0.08401(15) 0.0490(4) Uani 1 1 d . . .
H17 H 0.7499 -0.2995 0.0099 0.059 Uiso 1 1 calc R . .
C19 C 0.6824(2) -0.16935(15) 0.12152(13) 0.0427(4) Uani 1 1 d . . .
H16 H 0.6589 -0.1097 0.0720 0.051 Uiso 1 1 calc R . .
C4 C 0.6587(2) 0.06698(14) 0.19938(12) 0.0382(4) Uani 1 1 d . . .
C5 C 0.5510(2) 0.16269(15) 0.16401(14) 0.0420(4) Uani 1 1 d . . .
C17 C 0.6198(3) 0.25015(17) 0.09102(16) 0.0535(5) Uani 1 1 d . . .
H7 H 0.6170 0.3139 0.1361 0.064 Uiso 1 1 calc R . .
H8 H 0.5407 0.2802 0.0406 0.064 Uiso 1 1 calc R . .
C16 C 0.8119(3) 0.19819(19) 0.02546(16) 0.0574(5) Uani 1 1 d . . .
H5 H 0.8117 0.1444 -0.0295 0.069 Uiso 1 1 calc R . .
H6 H 0.8595 0.2586 -0.0129 0.069 Uiso 1 1 calc R . .
C15 C 0.9312(3) 0.13674(18) 0.10061(17) 0.0556(5) Uani 1 1 d . . .
H4 H 0.9481 0.1933 0.1463 0.067 Uiso 1 1 calc R . .
H3 H 1.0498 0.0966 0.0560 0.067 Uiso 1 1 calc R . .
C14 C 0.8555(2) 0.05098(14) 0.17481(13) 0.0416(4) Uani 1 1 d . . .
C24 C 0.2996(3) -0.02190(17) 0.41041(15) 0.0524(5) Uani 1 1 d . . .
N2 N 0.2407(3) -0.0511(2) 0.49575(16) 0.0799(6) Uani 1 1 d . . .
H1 H 0.214(3) -0.006(2) 0.2241(19) 0.058(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
O2 C6 1.378(2) . ?
O2 C1 1.389(2) . ?
O6 N3 1.214(3) . ?
N1 C1 1.404(2) . ?
N1 C2 1.501(2) . ?
N1 H1 0.77(2) . ?
O4 C14 1.220(2) . ?
O1 C5 1.362(2) . ?
O1 C1 1.394(2) . ?
O3 C6 1.185(2) . ?
C1 C2 1.482(2) . ?
C3 C4 1.510(2) . ?
C3 C18 1.517(2) . ?
C3 C2 1.520(2) . ?
C3 H2 0.9800 . ?
C18 C23 1.384(3) . ?
C18 C19 1.388(2) . ?
C11 C10 1.353(5) . ?
C11 C12 1.362(6) . ?
C11 H13 0.9300 . ?
C12 C13 1.382(5) . ?
C12 H14 0.9300 . ?
C13 C8 1.360(4) . ?
C13 H15 0.9300 . ?
C8 C9 1.363(3) . ?
C8 C7 1.502(3) . ?
C7 C6 1.502(3) . ?
C7 H9 0.9700 . ?
C7 H10 0.9700 . ?
C2 C24 1.451(2) . ?
C23 C22 1.378(3) . ?
C23 H19 0.9300 . ?
C22 C21 1.369(3) . ?
C22 H18 0.9300 . ?
C21 C20 1.379(3) . ?
C21 N3 1.469(3) . ?
N3 O5 1.205(3) . ?
C9 C10 1.364(4) . ?
C9 H11 0.9300 . ?
C10 H12 0.9300 . ?
C20 C19 1.384(3) . ?
C20 H17 0.9300 . ?
C19 H16 0.9300 . ?
C4 C5 1.345(2) . ?
C4 C14 1.464(2) . ?
C5 C17 1.496(2) . ?
C17 C16 1.509(3) . ?
C17 H7 0.9700 . ?
C17 H8 0.9700 . ?
C16 C15 1.497(3) . ?
C16 H5 0.9700 . ?
C16 H6 0.9700 . ?
C15 C14 1.511(2) . ?
C15 H4 0.9700 . ?
C15 H3 0.9700 . ?
C24 N2 1.136(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
C6 O2 C1 117.52(14) . . ?
C1 N1 C2 61.27(11) . . ?
C1 N1 H1 110.3(17) . . ?
C2 N1 H1 110.5(17) . . ?
C5 O1 C1 117.73(13) . . ?
O2 C1 O1 108.55(14) . . ?
O2 C1 N1 117.43(14) . . ?
O1 C1 N1 117.39(14) . . ?
O2 C1 C2 122.26(14) . . ?
O1 C1 C2 121.87(13) . . ?
N1 C1 C2 62.58(11) . . ?
C4 C3 C18 114.98(13) . . ?
C4 C3 C2 109.89(13) . . ?
C18 C3 C2 108.68(12) . . ?
C4 C3 H2 107.7 . . ?
C18 C3 H2 107.7 . . ?
C2 C3 H2 107.7 . . ?
C23 C18 C19 119.11(16) . . ?
C23 C18 C3 119.29(15) . . ?
C19 C18 C3 121.51(14) . . ?
C10 C11 C12 118.4(3) . . ?
C10 C11 H13 120.8 . . ?
C12 C11 H13 120.8 . . ?
C11 C12 C13 120.8(3) . . ?
C11 C12 H14 119.6 . . ?
C13 C12 H14 119.6 . . ?
C8 C13 C12 120.7(3) . . ?
C8 C13 H15 119.7 . . ?
C12 C13 H15 119.7 . . ?
C13 C8 C9 117.6(2) . . ?
C13 C8 C7 122.0(2) . . ?
C9 C8 C7 120.3(2) . . ?
C8 C7 C6 114.9(2) . . ?
C8 C7 H9 108.5 . . ?
C6 C7 H9 108.5 . . ?
C8 C7 H10 108.5 . . ?
C6 C7 H10 108.5 . . ?
H9 C7 H10 107.5 . . ?
O3 C6 O2 122.08(18) . . ?
O3 C6 C7 129.80(19) . . ?
O2 C6 C7 108.11(17) . . ?
C24 C2 C1 117.83(15) . . ?
C24 C2 N1 119.47(14) . . ?
C1 C2 N1 56.15(10) . . ?
C24 C2 C3 115.42(14) . . ?
C1 C2 C3 120.31(14) . . ?
N1 C2 C3 114.73(13) . . ?
C22 C23 C18 120.37(18) . . ?
C22 C23 H19 119.8 . . ?
C18 C23 H19 119.8 . . ?
C21 C22 C23 119.40(18) . . ?
C21 C22 H18 120.3 . . ?
C23 C22 H18 120.3 . . ?
C22 C21 C20 121.91(19) . . ?
C22 C21 N3 119.62(19) . . ?
C20 C21 N3 118.46(18) . . ?
O5 N3 O6 122.6(2) . . ?
O5 N3 C21 118.8(2) . . ?
O6 N3 C21 118.6(2) . . ?
C8 C9 C10 121.9(3) . . ?
C8 C9 H11 119.1 . . ?
C10 C9 H11 119.1 . . ?
C11 C10 C9 120.6(3) . . ?
C11 C10 H12 119.7 . . ?
C9 C10 H12 119.7 . . ?
C21 C20 C19 118.15(16) . . ?
C21 C20 H17 120.9 . . ?
C19 C20 H17 120.9 . . ?
C20 C19 C18 121.04(15) . . ?
C20 C19 H16 119.5 . . ?
C18 C19 H16 119.5 . . ?
C5 C4 C14 118.90(14) . . ?
C5 C4 C3 124.89(14) . . ?
C14 C4 C3 115.76(13) . . ?
C4 C5 O1 124.93(15) . . ?
C4 C5 C17 124.23(15) . . ?
O1 C5 C17 110.83(14) . . ?
C5 C17 C16 111.23(15) . . ?
C5 C17 H7 109.4 . . ?
C16 C17 H7 109.4 . . ?
C5 C17 H8 109.4 . . ?
C16 C17 H8 109.4 . . ?
H7 C17 H8 108.0 . . ?
C15 C16 C17 110.31(16) . . ?
C15 C16 H5 109.6 . . ?
C17 C16 H5 109.6 . . ?
C15 C16 H6 109.6 . . ?
C17 C16 H6 109.6 . . ?
H5 C16 H6 108.1 . . ?
C16 C15 C14 113.57(15) . . ?
C16 C15 H4 108.9 . . ?
C14 C15 H4 108.9 . . ?
C16 C15 H3 108.9 . . ?
C14 C15 H3 108.9 . . ?
H4 C15 H3 107.7 . . ?
O4 C14 C4 119.94(14) . . ?
O4 C14 C15 121.63(15) . . ?
C4 C14 C15 118.38(14) . . ?
N2 C24 C2 176.8(2) . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.047
