# Electronic Supplementary Material (ESI) for New Journal of Chemistry
# This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 2013

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_drt07
#TrackingRef '15602_web_deposit_cif_file_0_Madhuprasad_1353572754.DRT07_FINALIZED.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_symmetry_space_group_name_Hall  '-P 2ybc'
_chemical_formula_moiety         'C13 H10 N2 O3'
_chemical_formula_sum            'C13 H10 N2 O3'
_chemical_formula_weight         242.23

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                   11.9767(8)
_cell_length_b                   5.9302(4)
_cell_length_c                   16.1269(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.635(2)
_cell_angle_gamma                90.00
_cell_volume                     1137.73(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      0.964
_cell_measurement_theta_max      0.973

_exptl_crystal_description       block
_exptl_crystal_colour            pink
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.27
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             504
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9533
_exptl_absorpt_correction_T_max  0.9728
_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            12717
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_sigmaI/netI    0.0157
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.71
_diffrn_reflns_theta_max         24.99
_reflns_number_total             1993
_reflns_number_gt                1758
_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 F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0871P)^2^+0.2423P] where P=(Fo^2^+2Fc^2^)/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         1993
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0523
_refine_ls_wR_factor_ref         0.1485
_refine_ls_wR_factor_gt          0.1314
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_restrained_S_all      1.113
_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 0.55309(11) 1.44344(19) 0.57773(8) 0.0568(4) Uani 1 1 d . . .
H1 H 0.4941 1.4053 0.5505 0.085 Uiso 1 1 calc R . .
C2 C 0.58690(12) 1.2797(2) 0.63405(9) 0.0385(4) Uani 1 1 d . . .
C3 C 0.68481(13) 1.3069(3) 0.68798(9) 0.0442(4) Uani 1 1 d . . .
H3 H 0.7272 1.4380 0.6866 0.053 Uiso 1 1 calc R . .
C4 C 0.71856(13) 1.1372(3) 0.74373(9) 0.0459(4) Uani 1 1 d . . .
H4 H 0.7848 1.1532 0.7795 0.055 Uiso 1 1 calc R . .
C5 C 0.65494(13) 0.9431(3) 0.74703(10) 0.0470(4) Uani 1 1 d . . .
H5 H 0.6783 0.8302 0.7852 0.056 Uiso 1 1 calc R . .
C6 C 0.55689(13) 0.9168(3) 0.69385(9) 0.0416(4) Uani 1 1 d . . .
H6 H 0.5142 0.7865 0.6965 0.050 Uiso 1 1 calc R . .
C7 C 0.52167(12) 1.0844(2) 0.63634(8) 0.0351(4) Uani 1 1 d . . .
N8 N 0.42345(10) 1.0853(2) 0.57849(7) 0.0384(3) Uani 1 1 d . . .
C9 C 0.35600(13) 0.9203(3) 0.57056(9) 0.0431(4) Uani 1 1 d . . .
H9 H 0.3718 0.7935 0.6037 0.052 Uiso 1 1 calc R . .
C10 C 0.25367(12) 0.9219(3) 0.51089(9) 0.0407(4) Uani 1 1 d . . .
C11 C 0.18196(15) 0.7366(3) 0.50758(11) 0.0548(5) Uani 1 1 d . . .
H11 H 0.1989 0.6155 0.5435 0.066 Uiso 1 1 calc R . .
C12 C 0.08570(15) 0.7312(3) 0.45126(11) 0.0581(5) Uani 1 1 d . . .
H12 H 0.0376 0.6076 0.4491 0.070 Uiso 1 1 calc R . .
C13 C 0.06232(13) 0.9117(3) 0.39854(11) 0.0501(4) Uani 1 1 d . . .
N14 N -0.03990(13) 0.9053(4) 0.33823(12) 0.0720(5) Uani 1 1 d . . .
O15 O -0.10841(13) 0.7583(4) 0.34700(13) 0.1098(7) Uani 1 1 d . . .
O16 O -0.05117(15) 1.0441(4) 0.28283(14) 0.1082(7) Uani 1 1 d . . .
C17 C 0.13229(14) 1.0967(3) 0.39935(11) 0.0509(4) Uani 1 1 d . . .
H17 H 0.1154 1.2156 0.3624 0.061 Uiso 1 1 calc R . .
C18 C 0.22781(14) 1.1019(3) 0.45603(10) 0.0448(4) Uani 1 1 d . . .
H18 H 0.2754 1.2262 0.4578 0.054 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0647(8) 0.0460(7) 0.0544(7) 0.0154(5) -0.0156(5) -0.0108(5)
C2 0.0434(8) 0.0388(8) 0.0325(7) 0.0011(6) 0.0012(6) 0.0010(6)
C3 0.0434(8) 0.0460(9) 0.0421(8) -0.0032(6) 0.0005(6) -0.0067(7)
C4 0.0374(8) 0.0600(10) 0.0384(8) -0.0023(7) -0.0034(6) 0.0024(7)
C5 0.0468(9) 0.0513(9) 0.0414(8) 0.0086(7) -0.0009(7) 0.0067(7)
C6 0.0427(8) 0.0411(8) 0.0406(8) 0.0040(6) 0.0036(6) -0.0001(6)
C7 0.0369(7) 0.0390(8) 0.0291(7) -0.0012(5) 0.0030(5) 0.0011(6)
N8 0.0385(7) 0.0419(7) 0.0340(6) -0.0010(5) 0.0000(5) -0.0013(5)
C9 0.0472(9) 0.0456(9) 0.0359(8) 0.0018(6) 0.0016(6) -0.0046(7)
C10 0.0400(8) 0.0461(9) 0.0361(8) -0.0047(6) 0.0050(6) -0.0049(6)
C11 0.0591(10) 0.0570(10) 0.0476(9) 0.0033(7) 0.0031(8) -0.0169(8)
C12 0.0500(10) 0.0682(12) 0.0562(10) -0.0080(9) 0.0069(8) -0.0245(8)
C13 0.0323(8) 0.0668(11) 0.0506(9) -0.0164(8) 0.0017(6) -0.0012(7)
N14 0.0393(9) 0.0938(14) 0.0793(12) -0.0255(10) -0.0087(8) -0.0008(9)
O15 0.0549(9) 0.1517(18) 0.1170(14) -0.0234(13) -0.0142(9) -0.0386(11)
O16 0.0783(11) 0.1100(14) 0.1219(16) 0.0105(12) -0.0496(10) 0.0085(10)
C17 0.0452(9) 0.0506(9) 0.0546(10) -0.0045(7) -0.0043(7) 0.0051(7)
C18 0.0411(8) 0.0425(8) 0.0493(9) -0.0048(7) -0.0014(7) -0.0039(6)

_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 C2 1.3588(18) . ?
O1 H1 0.8200 . ?
C2 C3 1.386(2) . ?
C2 C7 1.400(2) . ?
C3 C4 1.379(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.385(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.381(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.391(2) . ?
C6 H6 0.9300 . ?
C7 N8 1.4145(19) . ?
N8 C9 1.266(2) . ?
C9 C10 1.468(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.392(2) . ?
C10 C18 1.398(2) . ?
C11 C12 1.383(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.376(3) . ?
C12 H12 0.9300 . ?
C13 C17 1.380(2) . ?
C13 N14 1.474(2) . ?
N14 O16 1.211(3) . ?
N14 O15 1.217(3) . ?
C17 C18 1.380(2) . ?
C17 H17 0.9300 . ?
C18 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
C2 O1 H1 109.5 . . ?
O1 C2 C3 120.09(13) . . ?
O1 C2 C7 118.99(13) . . ?
C3 C2 C7 120.92(13) . . ?
C4 C3 C2 119.15(14) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C3 C4 C5 120.72(14) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 120.16(14) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C7 120.26(14) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C6 C7 C2 118.79(14) . . ?
C6 C7 N8 127.41(13) . . ?
C2 C7 N8 113.79(12) . . ?
C9 N8 C7 122.41(13) . . ?
N8 C9 C10 122.40(14) . . ?
N8 C9 H9 118.8 . . ?
C10 C9 H9 118.8 . . ?
C11 C10 C18 119.21(15) . . ?
C11 C10 C9 118.99(14) . . ?
C18 C10 C9 121.79(14) . . ?
C12 C11 C10 120.49(17) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C13 C12 C11 118.83(16) . . ?
C13 C12 H12 120.6 . . ?
C11 C12 H12 120.6 . . ?
C12 C13 C17 122.22(15) . . ?
C12 C13 N14 118.81(16) . . ?
C17 C13 N14 118.96(17) . . ?
O16 N14 O15 123.62(19) . . ?
O16 N14 C13 118.87(18) . . ?
O15 N14 C13 117.5(2) . . ?
C13 C17 C18 118.70(16) . . ?
C13 C17 H17 120.6 . . ?
C18 C17 H17 120.6 . . ?
C17 C18 C10 120.55(15) . . ?
C17 C18 H18 119.7 . . ?
C10 C18 H18 119.7 . . ?

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
O1 H1 O1 0.82 2.26 2.760(2) 119.3 3_686

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.418
_refine_diff_density_rms         0.132


_database_code_depnum_ccdc_archive 'CCDC 912057'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_mo_nitk97_0m_a

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          367.5
_chemical_formula_moiety         'C13 H10 N2 O2'
_chemical_formula_sum            'C13 H10 N2 O2'
_chemical_formula_weight         226.23

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)/n

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

_cell_length_a                   14.6480(2)
_cell_length_b                   10.8265(2)
_cell_length_c                   14.7278(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.9400(10)
_cell_angle_gamma                90.00
_cell_volume                     2285.10(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.26
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             944
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9455
_exptl_absorpt_correction_T_max  0.9643
_exptl_absorpt_process_details   SADABS

_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31249
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_av_sigmaI/netI    0.0215
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.78
_diffrn_reflns_theta_max         26.00
_reflns_number_total             4493
_reflns_number_gt                2972
_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 F^2^ against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F^2^, conventional R-factors R are based 
 on F, with F set to zero for negative F^2^. The threshold expression of 
 F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F^2^ 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/[\s^2^(Fo^2^)+(0.0575P)^2^+0.7502P] where P=(Fo^2^+2Fc^2^)/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         4493
_refine_ls_number_parameters     387
_refine_ls_number_restraints     82
_refine_ls_R_factor_all          0.1054
_refine_ls_R_factor_gt           0.0685
_refine_ls_wR_factor_ref         0.1580
_refine_ls_wR_factor_gt          0.1440
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_restrained_S_all      1.092
_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 0.47616(15) 0.82962(19) 0.78413(12) 0.0898(6) Uani 1 1 d U . .
N2 N 0.52383(12) 0.78993(18) 0.32379(13) 0.0585(5) Uani 1 1 d U . .
N4 N 0.51724(16) 0.7417(2) 0.76008(14) 0.0735(6) Uani 1 1 d U . .
N3 N 0.28534(15) 0.5509(2) -0.28366(15) 0.0759(6) Uani 1 1 d U . .
N1 N 0.23163(14) 0.5425(2) 0.14042(14) 0.0703(6) Uani 1 1 d U . .
C17 C 0.54652(14) 0.7227(2) 0.48170(14) 0.0527(5) Uani 1 1 d U . .
O1 O 0.31878(17) 0.6337(2) -0.32109(14) 0.1169(8) Uani 1 1 d U . .
O2 O 0.25665(18) 0.4571(2) -0.32402(14) 0.1094(7) Uani 1 1 d U . .
C16 C 0.50310(16) 0.8235(2) 0.51303(16) 0.0554(6) Uani 1 1 d U . .
O4 O 0.54754(19) 0.6564(2) 0.81114(14) 0.1158(8) Uani 1 1 d U . .
C14 C 0.52915(15) 0.7367(2) 0.66334(14) 0.0553(6) Uani 1 1 d U . .
C15 C 0.49451(16) 0.8309(2) 0.60402(16) 0.0576(6) Uani 1 1 d U . .
C20 C 0.55481(16) 0.7112(3) 0.38445(16) 0.0591(6) Uani 1 1 d U . .
C8 C 0.23177(15) 0.5695(2) 0.23567(15) 0.0567(6) Uani 1 1 d U . .
C1 C 0.27705(15) 0.5663(2) -0.18691(16) 0.0609(6) Uani 1 1 d U . .
C21 C 0.53105(14) 0.7670(2) 0.23080(15) 0.0584(6) Uani 1 1 d U . .
C4 C 0.26315(16) 0.6003(2) -0.00640(16) 0.0637(6) Uani 1 1 d U . .
C9 C 0.17396(18) 0.4983(2) 0.27713(18) 0.0652(6) Uani 1 1 d U . .
C7 C 0.25675(18) 0.6221(3) 0.09216(19) 0.0715(7) Uani 1 1 d U . .
C18 C 0.58163(18) 0.6307(3) 0.54401(18) 0.0692(7) Uani 1 1 d U . .
C19 C 0.57346(19) 0.6373(3) 0.63501(18) 0.0699(7) Uani 1 1 d U . .
C6 C 0.29909(19) 0.6775(3) -0.14554(19) 0.0737(7) Uani 1 1 d U . .
C10 C 0.1720(2) 0.5146(3) 0.3691(2) 0.0785(8) Uani 1 1 d U . .
C13 C 0.28799(19) 0.6558(3) 0.2887(2) 0.0758(7) Uani 1 1 d U . .
C26 C 0.55102(18) 0.8650(3) 0.17880(19) 0.0746(7) Uani 1 1 d U . .
C22 C 0.5141(2) 0.6522(3) 0.18956(19) 0.0775(8) Uani 1 1 d U . .
C11 C 0.2276(2) 0.6008(3) 0.4206(2) 0.0833(9) Uani 1 1 d U . .
C5 C 0.2914(2) 0.6937(3) -0.0559(2) 0.0786(8) Uani 1 1 d U . .
C3 C 0.2418(2) 0.4871(3) -0.0485(2) 0.0807(8) Uani 1 1 d U . .
C12 C 0.2859(2) 0.6711(3) 0.3803(2) 0.0874(9) Uani 1 1 d U . .
C2 C 0.2475(2) 0.4690(3) -0.1405(2) 0.0833(8) Uani 1 1 d U . .
C25 C 0.5573(2) 0.8477(5) 0.0876(2) 0.0954(10) Uani 1 1 d U . .
C24 C 0.5410(2) 0.7340(5) 0.0476(2) 0.1090(13) Uani 1 1 d U . .
C23 C 0.5192(3) 0.6367(4) 0.0987(2) 0.1029(11) Uani 1 1 d U . .
H3 H 0.225(2) 0.421(3) -0.020(2) 0.107(10) Uiso 1 1 d . . .
H4 H 0.236(2) 0.394(3) -0.171(2) 0.103(10) Uiso 1 1 d . . .
H1 H 0.320(2) 0.741(3) -0.179(2) 0.112(11) Uiso 1 1 d . . .
H5 H 0.276(2) 0.709(3) 0.116(2) 0.132(12) Uiso 1 1 d . . .
H2 H 0.309(2) 0.773(3) -0.022(2) 0.107(10) Uiso 1 1 d . . .
H6 H 0.1318(17) 0.439(2) 0.2383(17) 0.083(8) Uiso 1 1 d . . .
H7 H 0.128(2) 0.468(3) 0.3961(19) 0.107(10) Uiso 1 1 d . . .
H9 H 0.325(2) 0.733(3) 0.419(2) 0.116(11) Uiso 1 1 d . . .
H8 H 0.2270(18) 0.611(2) 0.4802(19) 0.087(9) Uiso 1 1 d . . .
H10 H 0.3291(18) 0.704(2) 0.2610(17) 0.088(8) Uiso 1 1 d . . .
H14 H 0.4633(16) 0.900(2) 0.6234(15) 0.072(7) Uiso 1 1 d . . .
H13 H 0.4777(15) 0.886(2) 0.4708(15) 0.061(6) Uiso 1 1 d . . .
H11 H 0.5953(16) 0.580(2) 0.6774(16) 0.069(7) Uiso 1 1 d . . .
H12 H 0.6106(16) 0.565(2) 0.5229(16) 0.077(8) Uiso 1 1 d . . .
H15 H 0.5863(17) 0.639(2) 0.3718(16) 0.077(7) Uiso 1 1 d . . .
H20 H 0.5613(18) 0.945(3) 0.2073(18) 0.082(8) Uiso 1 1 d . . .
H16 H 0.4985(18) 0.586(3) 0.2232(18) 0.083(9) Uiso 1 1 d . . .
H17 H 0.505(2) 0.556(3) 0.071(2) 0.122(12) Uiso 1 1 d . . .
H19 H 0.569(2) 0.920(3) 0.056(2) 0.115(12) Uiso 1 1 d . . .
H18 H 0.542(2) 0.726(3) -0.010(3) 0.128(13) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O3 0.1219(16) 0.0831(13) 0.0751(12) -0.0190(10) 0.0446(11) -0.0192(12)
N2 0.0556(11) 0.0688(12) 0.0510(11) -0.0052(10) 0.0112(9) 0.0018(10)
N4 0.0902(16) 0.0751(15) 0.0560(13) -0.0033(12) 0.0168(12) -0.0228(13)
N3 0.0745(15) 0.0881(17) 0.0677(14) -0.0035(13) 0.0202(12) -0.0042(13)
N1 0.0621(13) 0.0776(15) 0.0700(13) 0.0092(11) 0.0108(10) 0.0000(11)
C17 0.0474(12) 0.0579(13) 0.0515(12) -0.0062(11) 0.0072(10) 0.0002(10)
O1 0.1349(19) 0.145(2) 0.0775(13) 0.0007(13) 0.0379(13) -0.0550(17)
O2 0.155(2) 0.0928(15) 0.0876(14) -0.0235(12) 0.0428(14) -0.0083(15)
C16 0.0619(14) 0.0528(14) 0.0500(13) -0.0010(11) 0.0085(11) 0.0003(11)
O4 0.178(2) 0.1088(17) 0.0615(12) 0.0193(12) 0.0265(13) 0.0098(16)
C14 0.0579(13) 0.0605(14) 0.0467(12) -0.0051(11) 0.0090(10) -0.0131(11)
C15 0.0639(15) 0.0532(14) 0.0571(14) -0.0075(11) 0.0157(11) -0.0018(12)
C20 0.0551(14) 0.0670(16) 0.0552(14) -0.0108(12) 0.0115(11) 0.0076(12)
C8 0.0520(13) 0.0631(14) 0.0525(13) 0.0015(11) 0.0051(10) 0.0095(11)
C1 0.0536(13) 0.0715(16) 0.0583(14) -0.0005(12) 0.0133(11) 0.0009(12)
C21 0.0467(12) 0.0803(17) 0.0482(13) -0.0045(12) 0.0098(10) 0.0051(11)
C4 0.0503(13) 0.0780(17) 0.0613(14) -0.0035(13) 0.0080(11) 0.0013(12)
C9 0.0642(15) 0.0635(16) 0.0651(16) 0.0046(13) 0.0072(13) -0.0039(13)
C7 0.0619(16) 0.0690(18) 0.0811(18) 0.0027(15) 0.0093(13) 0.0000(13)
C18 0.0742(17) 0.0694(17) 0.0641(16) -0.0019(13) 0.0148(13) 0.0218(14)
C19 0.0770(17) 0.0688(17) 0.0593(16) 0.0122(14) 0.0036(13) 0.0096(14)
C6 0.0816(18) 0.0703(18) 0.0711(17) 0.0012(14) 0.0201(14) -0.0069(14)
C10 0.0684(17) 0.099(2) 0.0694(18) 0.0166(16) 0.0168(14) -0.0006(16)
C13 0.0690(17) 0.0818(19) 0.0778(18) -0.0061(15) 0.0179(14) -0.0132(15)
C26 0.0689(17) 0.090(2) 0.0667(17) 0.0038(16) 0.0184(13) 0.0046(15)
C22 0.0827(19) 0.091(2) 0.0583(16) -0.0167(15) 0.0138(14) -0.0054(16)
C11 0.0681(18) 0.122(3) 0.0581(17) -0.0081(17) 0.0099(15) 0.0154(17)
C5 0.092(2) 0.0755(19) 0.0707(17) -0.0032(15) 0.0217(15) -0.0077(15)
C3 0.088(2) 0.083(2) 0.0757(19) 0.0131(16) 0.0274(15) -0.0126(16)
C12 0.0751(19) 0.099(2) 0.085(2) -0.0291(18) 0.0099(16) -0.0117(17)
C2 0.103(2) 0.0720(19) 0.0780(19) -0.0066(16) 0.0254(16) -0.0168(16)
C25 0.082(2) 0.140(3) 0.069(2) 0.022(2) 0.0260(16) 0.012(2)
C24 0.093(2) 0.186(4) 0.0481(19) -0.012(2) 0.0150(17) 0.016(2)
C23 0.107(3) 0.133(3) 0.067(2) -0.035(2) 0.0156(18) 0.000(2)

_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 N4 1.217(3) . ?
N2 C20 1.250(3) . ?
N2 C21 1.417(3) . ?
N4 O4 1.216(3) . ?
N4 C14 1.472(3) . ?
N3 O1 1.208(3) . ?
N3 O2 1.208(3) . ?
N3 C1 1.464(3) . ?
N1 C7 1.221(3) . ?
N1 C8 1.432(3) . ?
C17 C18 1.379(3) . ?
C17 C16 1.389(3) . ?
C17 C20 1.468(3) . ?
C16 C15 1.374(3) . ?
C14 C19 1.366(3) . ?
C14 C15 1.370(3) . ?
C8 C13 1.377(3) . ?
C8 C9 1.378(3) . ?
C1 C6 1.358(3) . ?
C1 C2 1.374(4) . ?
C21 C26 1.375(4) . ?
C21 C22 1.383(4) . ?
C4 C5 1.360(4) . ?
C4 C3 1.380(4) . ?
C4 C7 1.492(4) . ?
C9 C10 1.372(4) . ?
C18 C19 1.372(3) . ?
C6 C5 1.359(4) . ?
C10 C11 1.362(4) . ?
C13 C12 1.365(4) . ?
C26 C25 1.378(4) . ?
C22 C23 1.366(4) . ?
C11 C12 1.367(4) . ?
C3 C2 1.389(4) . ?
C25 C24 1.363(5) . ?
C24 C23 1.370(6) . ?

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
C20 N2 C21 118.9(2) . . ?
O4 N4 O3 123.6(2) . . ?
O4 N4 C14 118.0(2) . . ?
O3 N4 C14 118.4(2) . . ?
O1 N3 O2 122.1(2) . . ?
O1 N3 C1 118.9(2) . . ?
O2 N3 C1 119.0(2) . . ?
C7 N1 C8 119.1(2) . . ?
C18 C17 C16 118.6(2) . . ?
C18 C17 C20 119.6(2) . . ?
C16 C17 C20 121.8(2) . . ?
C15 C16 C17 120.7(2) . . ?
C19 C14 C15 121.9(2) . . ?
C19 C14 N4 118.9(2) . . ?
C15 C14 N4 119.2(2) . . ?
C14 C15 C16 118.8(2) . . ?
N2 C20 C17 123.3(2) . . ?
C13 C8 C9 118.6(2) . . ?
C13 C8 N1 125.0(2) . . ?
C9 C8 N1 116.3(2) . . ?
C6 C1 C2 121.8(2) . . ?
C6 C1 N3 118.5(2) . . ?
C2 C1 N3 119.7(2) . . ?
C26 C21 C22 119.2(2) . . ?
C26 C21 N2 118.1(2) . . ?
C22 C21 N2 122.6(2) . . ?
C5 C4 C3 119.0(2) . . ?
C5 C4 C7 119.4(3) . . ?
C3 C4 C7 121.5(2) . . ?
C10 C9 C8 120.4(3) . . ?
N1 C7 C4 122.8(3) . . ?
C19 C18 C17 121.1(2) . . ?
C14 C19 C18 118.9(2) . . ?
C1 C6 C5 119.4(3) . . ?
C11 C10 C9 120.4(3) . . ?
C12 C13 C8 120.7(3) . . ?
C21 C26 C25 120.2(3) . . ?
C23 C22 C21 120.0(3) . . ?
C10 C11 C12 119.6(3) . . ?
C6 C5 C4 121.4(3) . . ?
C4 C3 C2 120.7(3) . . ?
C13 C12 C11 120.3(3) . . ?
C1 C2 C3 117.8(3) . . ?
C24 C25 C26 120.2(4) . . ?
C25 C24 C23 119.8(3) . . ?
C22 C23 C24 120.6(4) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.146
_refine_diff_density_rms         0.029
_database_code_depnum_ccdc_archive 'CCDC 939305'