# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1478332'
_audit_update_record             
;
2016-05-05 deposited with the CCDC.
2016-10-19 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 H12 N2 O3'
_chemical_formula_weight         256.26

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   Cc

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

_cell_length_a                   10.7683(4)
_cell_length_b                   13.4401(5)
_cell_length_c                   8.4892(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.755(2)
_cell_angle_gamma                90.00
_cell_volume                     1225.98(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    155(2)
_cell_measurement_reflns_used    380
_cell_measurement_theta_min      0.994
_cell_measurement_theta_max      26.40

_exptl_crystal_description       prismatic
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             536.0
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.985
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      155(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
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4910
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_sigmaI/netI    0.0279
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.43
_diffrn_reflns_theta_max         26.40
_reflns_number_total             2204
_reflns_number_gt                1980
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker Smart'
_computing_cell_refinement       'Bruker Smart'
_computing_data_reduction        'Bruker Saint'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.0464P)²+0.1480P] 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       0.0142(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.06(11)
_refine_ls_number_reflns         2204
_refine_ls_number_parameters     175
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0331
_refine_ls_wR_factor_ref         0.0842
_refine_ls_wR_factor_gt          0.0812
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C9 C 0.46704(16) 0.30343(15) 0.5853(2) 0.0390(4) Uani 1 1 d . . .
C14 C 0.43374(17) 0.23263(16) 0.4723(2) 0.0456(5) Uani 1 1 d . . .
H14 H 0.4458 0.1640 0.4954 0.055 Uiso 1 1 calc R . .
O2 O 0.74739(14) 0.20951(12) 1.41856(16) 0.0564(4) Uani 1 1 d . . .
H2 H 0.7807 0.2578 1.4679 0.085 Uiso 1 1 calc R . .
O3 O 0.64996(14) 0.07413(10) 1.22849(16) 0.0537(4) Uani 1 1 d . . .
O1 O 0.79581(15) 0.39963(12) 1.47338(19) 0.0726(5) Uani 1 1 d . . .
C12 C 0.36450(18) 0.36033(17) 0.2920(2) 0.0533(5) Uani 1 1 d . . .
H12 H 0.3295 0.3799 0.1911 0.064 Uiso 1 1 calc R . .
C13 C 0.38286(17) 0.26147(17) 0.3255(2) 0.0503(5) Uani 1 1 d . . .
H13 H 0.3606 0.2126 0.2478 0.060 Uiso 1 1 calc R . .
N2 N 0.51673(13) 0.26643(13) 0.73422(17) 0.0419(4) Uani 1 1 d . . .
N1 N 0.55612(14) 0.33296(13) 0.82796(17) 0.0427(4) Uani 1 1 d . . .
C11 C 0.3969(2) 0.43174(16) 0.4049(3) 0.0528(5) Uani 1 1 d . . .
H11 H 0.3839 0.5002 0.3815 0.063 Uiso 1 1 calc R . .
C6 C 0.60201(17) 0.29745(13) 0.9786(2) 0.0383(4) Uani 1 1 d . . .
C7 C 0.60022(17) 0.19713(13) 1.0245(2) 0.0382(4) Uani 1 1 d . . .
H7 H 0.5655 0.1485 0.9533 0.046 Uiso 1 1 calc R . .
C2 C 0.64805(16) 0.16874(14) 1.1709(2) 0.0395(4) Uani 1 1 d . . .
C3 C 0.70060(16) 0.24032(15) 1.2767(2) 0.0401(4) Uani 1 1 d . . .
C10 C 0.44822(18) 0.40363(14) 0.5516(2) 0.0460(4) Uani 1 1 d . . .
H10 H 0.4705 0.4526 0.6291 0.055 Uiso 1 1 calc R . .
C5 C 0.65060(16) 0.36827(15) 1.0821(2) 0.0427(4) Uani 1 1 d . . .
H5 H 0.6500 0.4364 1.0520 0.051 Uiso 1 1 calc R . .
C4 C 0.70071(15) 0.34027(15) 1.2313(2) 0.0421(4) Uani 1 1 d . . .
C1 C 0.5921(2) -0.00064(15) 1.1296(3) 0.0616(6) Uani 1 1 d . . .
H1A H 0.5057 0.0184 1.1010 0.092 Uiso 1 1 calc R . .
H1B H 0.5935 -0.0642 1.1863 0.092 Uiso 1 1 calc R . .
H1C H 0.6373 -0.0075 1.0337 0.092 Uiso 1 1 calc R . .
C8 C 0.7505(2) 0.41562(17) 1.3398(3) 0.0573(5) Uani 1 1 d . . .
H8 H 0.7477 0.4827 1.3045 0.069 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C9 C14 1.382(3) . ?
C9 C10 1.389(3) . ?
C9 N2 1.429(2) . ?
C14 C13 1.383(3) . ?
C14 H14 0.9500 . ?
O2 C3 1.340(2) . ?
O2 H2 0.8400 . ?
O3 C2 1.362(2) . ?
O3 C1 1.426(3) . ?
O1 C8 1.224(3) . ?
C12 C13 1.371(3) . ?
C12 C11 1.385(3) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
N2 N1 1.252(2) . ?
N1 C6 1.423(2) . ?
C11 C10 1.381(3) . ?
C11 H11 0.9500 . ?
C6 C5 1.375(3) . ?
C6 C7 1.404(2) . ?
C7 C2 1.368(3) . ?
C7 H7 0.9500 . ?
C2 C3 1.409(3) . ?
C3 C4 1.398(3) . ?
C10 H10 0.9500 . ?
C5 C4 1.395(2) . ?
C5 H5 0.9500 . ?
C4 C8 1.448(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C8 H8 0.9500 . ?

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
C14 C9 C10 119.79(18) . . ?
C14 C9 N2 116.08(17) . . ?
C10 C9 N2 124.11(18) . . ?
C9 C14 C13 120.13(19) . . ?
C9 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C3 O2 H2 109.5 . . ?
C2 O3 C1 116.79(15) . . ?
C13 C12 C11 120.09(18) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C14 120.15(19) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
N1 N2 C9 113.90(15) . . ?
N2 N1 C6 114.51(15) . . ?
C10 C11 C12 120.15(18) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C5 C6 C7 119.93(16) . . ?
C5 C6 N1 115.93(15) . . ?
C7 C6 N1 124.13(16) . . ?
C2 C7 C6 120.58(17) . . ?
C2 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
O3 C2 C7 125.64(17) . . ?
O3 C2 C3 114.34(16) . . ?
C7 C2 C3 120.02(17) . . ?
O2 C3 C4 122.52(17) . . ?
O2 C3 C2 118.27(17) . . ?
C4 C3 C2 119.20(17) . . ?
C11 C10 C9 119.68(19) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C6 C5 C4 120.10(17) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C4 C3 120.15(17) . . ?
C5 C4 C8 119.57(18) . . ?
C3 C4 C8 120.27(18) . . ?
O3 C1 H1A 109.5 . . ?
O3 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O3 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C8 C4 125.1(2) . . ?
O1 C8 H8 117.4 . . ?
C4 C8 H8 117.4 . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        26.40
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.150
_refine_diff_density_min         -0.120
_refine_diff_density_rms         0.026
####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1478333'
_audit_update_record             
;
2016-05-05 deposited with the CCDC.
2016-10-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C31 H30 N6 O4'
_chemical_formula_weight         550.61

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                   8.648(2)
_cell_length_b                   11.051(3)
_cell_length_c                   13.816(4)
_cell_angle_alpha                91.833(9)
_cell_angle_beta                 97.710(9)
_cell_angle_gamma                92.902(8)
_cell_volume                     1305.8(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    360
_cell_measurement_theta_min      0.967
_cell_measurement_theta_max      23.56

_exptl_crystal_description       Block
_exptl_crystal_colour            Orange
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             580
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9830
_exptl_absorpt_correction_T_max  0.9962
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(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
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12084
_diffrn_reflns_av_R_equivalents  0.0726
_diffrn_reflns_av_sigmaI/netI    0.0769
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.33
_diffrn_reflns_theta_max         23.56
_reflns_number_total             3806
_reflns_number_gt                2308
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker Smart'
_computing_cell_refinement       'Bruker Smart'
_computing_data_reduction        'Bruker Saint'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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     SHELXL
_refine_ls_extinction_coef       0.13(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3806
_refine_ls_number_parameters     373
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2097
_refine_ls_R_factor_gt           0.1616
_refine_ls_wR_factor_ref         0.4619
_refine_ls_wR_factor_gt          0.4275
_refine_ls_goodness_of_fit_ref   1.753
_refine_ls_restrained_S_all      1.753
_refine_ls_shift/su_max          0.030
_refine_ls_shift/su_mean         0.005

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 0.9706(7) 0.5439(4) 0.3863(4) 0.0514(18) Uani 1 1 d . . .
H1 H 1.0352 0.5633 0.4360 0.077 Uiso 1 1 calc R . .
O2 O 0.7860(7) 0.9392(4) 0.5274(5) 0.058(2) Uani 1 1 d . . .
H2 H 0.8522 0.9139 0.5711 0.087 Uiso 1 1 calc R . .
O3 O 0.7748(7) 0.5157(4) 0.2221(4) 0.0559(19) Uani 1 1 d . . .
O4 O 0.5600(7) 0.9881(5) 0.3913(5) 0.063(2) Uani 1 1 d . . .
N1 N 0.8481(9) 0.9489(6) 0.1714(6) 0.059(2) Uani 1 1 d . . .
N2 N 0.7829(12) 0.9332(6) 0.0879(6) 0.090(4) Uani 1 1 d . . .
N3 N 1.1666(8) 0.6822(5) 0.5092(5) 0.046(2) Uani 1 1 d . . .
N4 N 0.9367(8) 0.7798(5) 0.6332(5) 0.050(2) Uani 1 1 d . . .
N5 N 0.4340(8) 0.5494(6) 0.3377(5) 0.052(2) Uani 1 1 d . . .
N6 N 0.3339(8) 0.5728(6) 0.2660(5) 0.050(2) Uani 1 1 d . . .
C1 C 0.9450(9) 0.6358(6) 0.3363(6) 0.044(2) Uani 1 1 d . . .
C2 C 1.0211(10) 0.7555(7) 0.3675(6) 0.049(2) Uani 1 1 d . . .
C3 C 0.9813(11) 0.8564(7) 0.3095(6) 0.052(3) Uani 1 1 d . . .
H3 H 1.0291 0.9341 0.3294 0.063 Uiso 1 1 calc R . .
C4 C 0.8769(10) 0.8448(6) 0.2263(6) 0.051(3) Uani 1 1 d . . .
C5 C 0.8085(10) 0.7292(7) 0.1925(6) 0.050(2) Uani 1 1 d . . .
H5 H 0.7414 0.7213 0.1321 0.060 Uiso 1 1 calc R . .
C6 C 0.8381(10) 0.6292(6) 0.2459(6) 0.046(2) Uani 1 1 d . . .
C7 C 0.6731(11) 0.4987(7) 0.1303(7) 0.061(3) Uani 1 1 d . . .
H7A H 0.5788 0.5435 0.1334 0.073 Uiso 1 1 calc R . .
H7B H 0.6437 0.4122 0.1180 0.073 Uiso 1 1 calc R . .
H7C H 0.7276 0.5287 0.0774 0.073 Uiso 1 1 calc R . .
C8 C 0.7427(13) 1.0397(8) 0.0364(7) 0.069(4) Uani 1 1 d . . .
C9 C 0.8097(13) 1.0644(9) -0.0481(10) 0.078(3) Uani 1 1 d . . .
H9 H 0.8840 1.0123 -0.0689 0.093 Uiso 1 1 calc R . .
C10 C 0.7693(15) 1.1612(9) -0.1000(10) 0.089(4) Uani 1 1 d . . .
H10 H 0.8217 1.1810 -0.1541 0.107 Uiso 1 1 calc R . .
C11 C 0.6535(12) 1.2320(7) -0.0759(7) 0.063(3) Uani 1 1 d . . .
H11 H 0.6255 1.2999 -0.1136 0.076 Uiso 1 1 calc R . .
C12 C 0.5774(14) 1.2049(7) 0.0029(8) 0.071(3) Uani 1 1 d . . .
H12 H 0.4921 1.2502 0.0172 0.085 Uiso 1 1 calc R . .
C13 C 0.6281(17) 1.1090(8) 0.0621(8) 0.086(4) Uani 1 1 d . . .
H13 H 0.5825 1.0929 0.1195 0.103 Uiso 1 1 calc R . .
C14 C 1.1296(10) 0.7696(7) 0.4522(6) 0.049(2) Uani 1 1 d . . .
H14 H 1.1787 0.8477 0.4688 0.059 Uiso 1 1 calc R . .
C15 C 1.2757(10) 0.7007(7) 0.6008(6) 0.049(2) Uani 1 1 d . . .
H15A H 1.3786 0.7305 0.5845 0.059 Uiso 1 1 calc R . .
H15B H 1.2897 0.6212 0.6309 0.059 Uiso 1 1 calc R . .
C16 C 1.2247(10) 0.7894(7) 0.6763(7) 0.054(3) Uani 1 1 d . . .
H16A H 1.3059 0.7960 0.7343 0.064 Uiso 1 1 calc R . .
H16B H 1.2184 0.8705 0.6481 0.064 Uiso 1 1 calc R . .
C17 C 1.0694(10) 0.7541(7) 0.7091(7) 0.053(3) Uani 1 1 d . . .
H17A H 1.0650 0.6665 0.7224 0.064 Uiso 1 1 calc R . .
H17B H 1.0595 0.7998 0.7706 0.064 Uiso 1 1 calc R . .
C18 C 0.8375(10) 0.6993(7) 0.5892(7) 0.053(2) Uani 1 1 d . . .
H18 H 0.8458 0.6174 0.6070 0.063 Uiso 1 1 calc R . .
C19 C 0.7179(9) 0.7267(7) 0.5161(6) 0.048(2) Uani 1 1 d . . .
C20 C 0.6984(10) 0.8493(7) 0.4865(7) 0.051(3) Uani 1 1 d . . .
C21 C 0.5740(10) 0.8677(7) 0.4089(7) 0.052(3) Uani 1 1 d . . .
C22 C 0.4387(11) 1.0112(7) 0.3085(7) 0.064(3) Uani 1 1 d . . .
H22A H 0.4587 0.9652 0.2501 0.077 Uiso 1 1 calc R . .
H22B H 0.4417 1.0980 0.2958 0.077 Uiso 1 1 calc R . .
H22C H 0.3355 0.9857 0.3249 0.077 Uiso 1 1 calc R . .
C23 C 0.4851(10) 0.7731(7) 0.3613(7) 0.053(3) Uani 1 1 d . . .
H23 H 0.4046 0.7880 0.3100 0.064 Uiso 1 1 calc R . .
C24 C 0.5123(10) 0.6524(7) 0.3880(6) 0.046(2) Uani 1 1 d . . .
C25 C 0.6228(9) 0.6295(7) 0.4639(6) 0.044(2) Uani 1 1 d . . .
H25 H 0.6371 0.5483 0.4824 0.053 Uiso 1 1 calc R . .
C26 C 0.2675(11) 0.4691(7) 0.2118(7) 0.055(2) Uani 1 1 d . . .
C27 C 0.1372(11) 0.4858(9) 0.1472(7) 0.064(3) Uani 1 1 d . . .
H27 H 0.0937 0.5630 0.1436 0.077 Uiso 1 1 calc R . .
C28 C 0.0687(12) 0.3903(9) 0.0871(8) 0.070(3) Uani 1 1 d . . .
H28 H -0.0236 0.4011 0.0433 0.084 Uiso 1 1 calc R . .
C29 C 0.1336(11) 0.2811(8) 0.0907(7) 0.064(3) Uani 1 1 d . . .
H29 H 0.0864 0.2167 0.0478 0.077 Uiso 1 1 calc R . .
C30 C 0.2641(12) 0.2606(8) 0.1536(7) 0.062(3) Uani 1 1 d . . .
H30 H 0.3067 0.1831 0.1552 0.074 Uiso 1 1 calc R . .
C31 C 0.3335(11) 0.3556(7) 0.2154(7) 0.061(3) Uani 1 1 d . . .
H31 H 0.4249 0.3437 0.2597 0.073 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.258(8) . ?
O1 H1 0.8400 . ?
O2 C20 1.286(9) . ?
O2 H2 0.8400 . ?
O3 C6 1.355(9) . ?
O3 C7 1.445(9) . ?
O4 C21 1.369(9) . ?
O4 C22 1.483(9) . ?
N1 N2 1.217(9) . ?
N1 C4 1.413(9) . ?
N2 C8 1.429(11) . ?
N3 C14 1.291(9) . ?
N3 C15 1.475(9) . ?
N4 C18 1.282(10) . ?
N4 C17 1.492(9) . ?
N5 N6 1.267(9) . ?
N5 C24 1.408(10) . ?
N6 C26 1.403(11) . ?
C1 C6 1.448(10) . ?
C1 C2 1.473(10) . ?
C2 C14 1.398(11) . ?
C2 C3 1.423(10) . ?
C3 C4 1.362(10) . ?
C3 H3 0.9500 . ?
C4 C5 1.418(10) . ?
C5 C6 1.364(10) . ?
C5 H5 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C13 1.360(16) . ?
C8 C9 1.399(16) . ?
C9 C10 1.342(14) . ?
C9 H9 0.9500 . ?
C10 C11 1.371(15) . ?
C10 H10 0.9500 . ?
C11 C12 1.379(15) . ?
C11 H11 0.9500 . ?
C12 C13 1.411(13) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.533(13) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.511(13) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.396(11) . ?
C18 H18 0.9500 . ?
C19 C25 1.433(11) . ?
C19 C20 1.440(10) . ?
C20 C21 1.441(11) . ?
C21 C23 1.362(12) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C24 1.417(10) . ?
C23 H23 0.9500 . ?
C24 C25 1.360(10) . ?
C25 H25 0.9500 . ?
C26 C27 1.365(12) . ?
C26 C31 1.405(12) . ?
C27 C28 1.379(14) . ?
C27 H27 0.9500 . ?
C28 C29 1.356(13) . ?
C28 H28 0.9500 . ?
C29 C30 1.362(12) . ?
C29 H29 0.9500 . ?
C30 C31 1.390(12) . ?
C30 H30 0.9500 . ?
C31 H31 0.9500 . ?

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
C1 O1 H1 109.5 . . ?
C20 O2 H2 109.5 . . ?
C6 O3 C7 117.0(5) . . ?
C21 O4 C22 113.7(6) . . ?
N2 N1 C4 117.3(7) . . ?
N1 N2 C8 116.5(7) . . ?
C14 N3 C15 122.5(6) . . ?
C18 N4 C17 124.8(6) . . ?
N6 N5 C24 114.4(6) . . ?
N5 N6 C26 113.4(6) . . ?
O1 C1 C6 121.6(6) . . ?
O1 C1 C2 121.6(6) . . ?
C6 C1 C2 116.8(6) . . ?
C14 C2 C3 120.9(7) . . ?
C14 C2 C1 120.7(6) . . ?
C3 C2 C1 118.5(6) . . ?
C4 C3 C2 121.9(7) . . ?
C4 C3 H3 119.0 . . ?
C2 C3 H3 119.0 . . ?
C3 C4 N1 118.2(6) . . ?
C3 C4 C5 120.3(7) . . ?
N1 C4 C5 121.3(6) . . ?
C6 C5 C4 120.7(7) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
O3 C6 C5 125.5(7) . . ?
O3 C6 C1 112.9(6) . . ?
C5 C6 C1 121.6(6) . . ?
O3 C7 H7A 109.5 . . ?
O3 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O3 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C13 C8 C9 119.8(9) . . ?
C13 C8 N2 120.7(11) . . ?
C9 C8 N2 119.1(11) . . ?
C10 C9 C8 120.3(11) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.9 . . ?
C9 C10 C11 120.8(12) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C10 C11 C12 120.2(9) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C11 C12 C13 119.0(11) . . ?
C11 C12 H12 120.5 . . ?
C13 C12 H12 120.5 . . ?
C8 C13 C12 119.6(11) . . ?
C8 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
N3 C14 C2 123.6(7) . . ?
N3 C14 H14 118.2 . . ?
C2 C14 H14 118.2 . . ?
N3 C15 C16 115.1(7) . . ?
N3 C15 H15A 108.5 . . ?
C16 C15 H15A 108.5 . . ?
N3 C15 H15B 108.5 . . ?
C16 C15 H15B 108.5 . . ?
H15A C15 H15B 107.5 . . ?
C17 C16 C15 114.3(7) . . ?
C17 C16 H16A 108.7 . . ?
C15 C16 H16A 108.7 . . ?
C17 C16 H16B 108.7 . . ?
C15 C16 H16B 108.7 . . ?
H16A C16 H16B 107.6 . . ?
N4 C17 C16 111.2(7) . . ?
N4 C17 H17A 109.4 . . ?
C16 C17 H17A 109.4 . . ?
N4 C17 H17B 109.4 . . ?
C16 C17 H17B 109.4 . . ?
H17A C17 H17B 108.0 . . ?
N4 C18 C19 123.0(7) . . ?
N4 C18 H18 118.5 . . ?
C19 C18 H18 118.5 . . ?
C18 C19 C25 119.1(7) . . ?
C18 C19 C20 121.1(7) . . ?
C25 C19 C20 119.6(7) . . ?
O2 C20 C19 122.2(7) . . ?
O2 C20 C21 120.9(6) . . ?
C19 C20 C21 116.9(7) . . ?
C23 C21 O4 126.5(7) . . ?
C23 C21 C20 121.8(7) . . ?
O4 C21 C20 111.7(7) . . ?
O4 C22 H22A 109.5 . . ?
O4 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O4 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 C24 120.3(7) . . ?
C21 C23 H23 119.8 . . ?
C24 C23 H23 119.8 . . ?
C25 C24 N5 115.5(6) . . ?
C25 C24 C23 120.7(7) . . ?
N5 C24 C23 123.8(7) . . ?
C24 C25 C19 120.5(7) . . ?
C24 C25 H25 119.7 . . ?
C19 C25 H25 119.7 . . ?
C27 C26 N6 115.9(7) . . ?
C27 C26 C31 119.9(8) . . ?
N6 C26 C31 124.0(8) . . ?
C26 C27 C28 119.9(8) . . ?
C26 C27 H27 120.0 . . ?
C28 C27 H27 120.0 . . ?
C29 C28 C27 119.8(9) . . ?
C29 C28 H28 120.1 . . ?
C27 C28 H28 120.1 . . ?
C28 C29 C30 122.3(9) . . ?
C28 C29 H29 118.9 . . ?
C30 C29 H29 118.9 . . ?
C29 C30 C31 118.6(8) . . ?
C29 C30 H30 120.7 . . ?
C31 C30 H30 120.7 . . ?
C30 C31 C26 119.4(8) . . ?
C30 C31 H31 120.3 . . ?
C26 C31 H31 120.3 . . ?

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
C14 H14 O2 0.95 2.36 3.258(9) 158.2 2_776
C16 H16B O4 0.99 2.54 3.246(10) 128.3 2_776
C17 H17A O3 0.99 2.58 3.442(9) 145.5 2_766
C18 H18 O1 0.95 2.44 3.233(9) 140.6 2_766
C22 H22C O2 0.98 2.55 3.229(14) 126.2 2_676

_diffrn_measured_fraction_theta_max 0.976
_diffrn_reflns_theta_full        23.56
_diffrn_measured_fraction_theta_full 0.976
_refine_diff_density_max         0.983
_refine_diff_density_min         -0.623
_refine_diff_density_rms         0.201
