# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 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_new
#TrackingRef 'sankararaman_34.cif'




_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;

?

;

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         'C9 H9 N3 O2'

_chemical_formula_sum            'C9 H9 N3 O2'

_chemical_formula_weight         191.19



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                   6.9540(3)

_cell_length_b                   7.6099(3)

_cell_length_c                   8.6454(3)

_cell_angle_alpha                106.098(2)

_cell_angle_beta                 101.881(2)

_cell_angle_gamma                93.586(2)

_cell_volume                     426.66(3)

_cell_formula_units_Z            2

_cell_measurement_temperature    298(2)

_cell_measurement_reflns_used    3447

_cell_measurement_theta_min      0.00

_cell_measurement_theta_max      0.00



_exptl_crystal_description       Block

_exptl_crystal_colour            Brown

_exptl_crystal_size_max          0.25

_exptl_crystal_size_mid          0.20

_exptl_crystal_size_min          0.12

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    1.488

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             200

_exptl_absorpt_coefficient_mu    0.109

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.9732

_exptl_absorpt_correction_T_max  0.9870

_exptl_absorpt_process_details   'SADABS (Bruker,2004)'



_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 APEXII CCD area detector'

_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean ?

_diffrn_standards_number         ?

_diffrn_standards_interval_count ?

_diffrn_standards_interval_time  ?

_diffrn_standards_decay_%        ?

_diffrn_reflns_number            5888

_diffrn_reflns_av_R_equivalents  0.0184

_diffrn_reflns_av_sigmaI/netI    0.0202

_diffrn_reflns_limit_h_min       -10

_diffrn_reflns_limit_h_max       8

_diffrn_reflns_limit_k_min       -10

_diffrn_reflns_limit_k_max       11

_diffrn_reflns_limit_l_min       -13

_diffrn_reflns_limit_l_max       11

_diffrn_reflns_theta_min         2.52

_diffrn_reflns_theta_max         33.88

_reflns_number_total             2247

_reflns_number_gt                1854

_reflns_threshold_expression     >2sigma(I)


_computing_data_collection       'APEXII, Bruker,2004'
_computing_cell_refinement       'APEXII/SAINT, Bruker,2004'
_computing_data_reduction        'SAINT PLUS/XPREP, Bruker,2004'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'



_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)+(0.0565P)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    constr

_refine_ls_extinction_method     none

_refine_ls_extinction_coef       ?

_refine_ls_number_reflns         2247

_refine_ls_number_parameters     129

_refine_ls_number_restraints     0

_refine_ls_R_factor_all          0.0495

_refine_ls_R_factor_gt           0.0401

_refine_ls_wR_factor_ref         0.1330

_refine_ls_wR_factor_gt          0.1273

_refine_ls_goodness_of_fit_ref   1.603

_refine_ls_restrained_S_all      1.603

_refine_ls_shift/su_max          0.000

_refine_ls_shift/su_mean         0.000



loop_

_atom_site_label

_atom_site_type_symbol

_atom_site_fract_x

_atom_site_fract_y

_atom_site_fract_z

_atom_site_U_iso_or_equiv

_atom_site_adp_type

_atom_site_occupancy

_atom_site_symmetry_multiplicity

_atom_site_calc_flag

_atom_site_refinement_flags

_atom_site_disorder_assembly

_atom_site_disorder_group























C1 C 0.40396(15) 0.22330(15) 1.00314(14) 0.0303(3) Uani 1 1 d . . .
C2 C 0.56491(16) 0.34434(17) 1.11068(15) 0.0373(3) Uani 1 1 d . . .
H2 H 0.5582 0.4030 1.2188 0.045 Uiso 1 1 calc R . .
C3 C 0.73468(17) 0.37840(18) 1.05873(18) 0.0430(3) Uani 1 1 d . . .
H3 H 0.8422 0.4582 1.1322 0.052 Uiso 1 1 calc R . .
C4 C 0.74456(16) 0.29392(18) 0.89767(18) 0.0444(3) Uani 1 1 d . . .
H4 H 0.8574 0.3197 0.8618 0.053 Uiso 1 1 calc R . .
C5 C 0.58810(16) 0.17181(18) 0.79012(16) 0.0386(3) Uani 1 1 d . . .
H5 H 0.5955 0.1148 0.6818 0.046 Uiso 1 1 calc R . .
C6 C 0.41842(14) 0.13325(15) 0.84320(13) 0.0289(3) Uani 1 1 d . . .
C7 C -0.00283(16) -0.19125(15) 0.60067(13) 0.0329(3) Uani 1 1 d . . .
C8 C 0.07222(15) -0.04022(16) 0.73324(14) 0.0336(3) Uani 1 1 d . . .
H8 H 0.0053 0.0245 0.8091 0.040 Uiso 1 1 calc R . .
C9 C -0.20561(18) -0.29605(18) 0.54409(15) 0.0426(3) Uani 1 1 d . . .
H9A H -0.3026 -0.2097 0.5461 0.051 Uiso 1 1 calc R . .
H9B H -0.2239 -0.3727 0.4306 0.051 Uiso 1 1 calc R . .
N1 N 0.26381(12) -0.00435(13) 0.73140(11) 0.0299(2) Uani 1 1 d . . .
N2 N 0.30866(14) -0.12894(14) 0.60273(12) 0.0407(3) Uani 1 1 d . . .
N3 N 0.14517(15) -0.24243(14) 0.52401(12) 0.0408(3) Uani 1 1 d . . .
O1 O 0.23413(11) 0.19318(12) 1.05050(10) 0.0427(3) Uani 1 1 d . . .
H1 H 0.2420 0.2617 1.1440 0.064 Uiso 1 1 calc R . .
O2 O -0.23971(13) -0.40936(12) 0.64407(10) 0.0465(3) Uani 1 1 d . . .
H2A H -0.2043 -0.5105 0.6080 0.070 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














C1 0.0308(5) 0.0288(6) 0.0320(6) 0.0092(5) 0.0094(4) 0.0020(4)
C2 0.0374(6) 0.0345(7) 0.0344(6) 0.0062(6) 0.0036(5) -0.0019(5)
C3 0.0309(5) 0.0406(7) 0.0530(8) 0.0131(6) 0.0030(5) -0.0026(5)
C4 0.0319(5) 0.0443(8) 0.0609(9) 0.0171(7) 0.0184(6) 0.0018(5)
C5 0.0387(6) 0.0380(7) 0.0430(7) 0.0101(6) 0.0204(5) 0.0062(5)
C6 0.0301(5) 0.0247(6) 0.0316(6) 0.0069(5) 0.0087(4) 0.0025(4)
C7 0.0397(6) 0.0308(7) 0.0251(5) 0.0033(5) 0.0086(5) 0.0011(5)
C8 0.0327(5) 0.0326(7) 0.0315(6) 0.0008(5) 0.0112(4) 0.0022(4)
C9 0.0422(6) 0.0422(8) 0.0331(6) -0.0004(6) 0.0049(5) -0.0042(5)
N1 0.0350(4) 0.0264(5) 0.0274(5) 0.0027(4) 0.0129(4) 0.0026(4)
N2 0.0469(5) 0.0364(6) 0.0349(6) -0.0037(5) 0.0214(5) 0.0010(5)
N3 0.0496(6) 0.0358(6) 0.0314(5) -0.0026(5) 0.0165(5) -0.0012(4)
O1 0.0399(4) 0.0475(6) 0.0323(5) -0.0049(4) 0.0173(4) -0.0101(4)
O2 0.0576(5) 0.0358(5) 0.0408(5) -0.0041(4) 0.0245(4) -0.0050(4)



_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 O1 1.3536(11) . ?
C1 C6 1.3900(16) . ?
C1 C2 1.3904(15) . ?
C2 C3 1.3810(15) . ?
C2 H2 0.9300 . ?
C3 C4 1.3804(19) . ?
C3 H3 0.9300 . ?
C4 C5 1.3747(18) . ?
C4 H4 0.9300 . ?
C5 C6 1.3940(14) . ?
C5 H5 0.9300 . ?
C6 N1 1.4341(14) . ?
C7 N3 1.3557(14) . ?
C7 C8 1.3620(16) . ?
C7 C9 1.4909(16) . ?
C8 N1 1.3474(12) . ?
C8 H8 0.9300 . ?
C9 O2 1.4210(15) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
N1 N2 1.3522(12) . ?
N2 N3 1.3169(13) . ?
O1 H1 0.8200 . ?
O2 H2A 0.8200 . ?



loop_

_geom_angle_atom_site_label_1

_geom_angle_atom_site_label_2

_geom_angle_atom_site_label_3

_geom_angle

_geom_angle_site_symmetry_1

_geom_angle_site_symmetry_3

_geom_angle_publ_flag





































O1 C1 C6 119.69(10) . . ?
O1 C1 C2 121.45(10) . . ?
C6 C1 C2 118.86(10) . . ?
C3 C2 C1 120.75(12) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C4 C3 C2 119.93(12) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C5 C4 C3 120.19(11) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 120.09(11) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C5 120.09(11) . . ?
C1 C6 N1 121.29(9) . . ?
C5 C6 N1 118.59(10) . . ?
N3 C7 C8 107.92(10) . . ?
N3 C7 C9 122.56(10) . . ?
C8 C7 C9 129.48(10) . . ?
N1 C8 C7 105.54(9) . . ?
N1 C8 H8 127.2 . . ?
C7 C8 H8 127.2 . . ?
O2 C9 C7 112.56(10) . . ?
O2 C9 H9A 109.1 . . ?
C7 C9 H9A 109.1 . . ?
O2 C9 H9B 109.1 . . ?
C7 C9 H9B 109.1 . . ?
H9A C9 H9B 107.8 . . ?
C8 N1 N2 110.37(9) . . ?
C8 N1 C6 130.98(9) . . ?
N2 N1 C6 118.59(9) . . ?
N3 N2 N1 106.60(9) . . ?
N2 N3 C7 109.57(9) . . ?
C1 O1 H1 109.5 . . ?
C9 O2 H2A 109.5 . . ?



loop_

_geom_torsion_atom_site_label_1

_geom_torsion_atom_site_label_2

_geom_torsion_atom_site_label_3

_geom_torsion_atom_site_label_4

_geom_torsion

_geom_torsion_site_symmetry_1

_geom_torsion_site_symmetry_2

_geom_torsion_site_symmetry_3

_geom_torsion_site_symmetry_4

_geom_torsion_publ_flag


























O1 C1 C2 C3 -177.76(11) . . . . ?
C6 C1 C2 C3 1.59(18) . . . . ?
C1 C2 C3 C4 0.99(19) . . . . ?
C2 C3 C4 C5 -1.9(2) . . . . ?
C3 C4 C5 C6 0.22(19) . . . . ?
O1 C1 C6 C5 176.09(10) . . . . ?
C2 C1 C6 C5 -3.27(17) . . . . ?
O1 C1 C6 N1 -5.87(17) . . . . ?
C2 C1 C6 N1 174.76(9) . . . . ?
C4 C5 C6 C1 2.40(18) . . . . ?
C4 C5 C6 N1 -175.69(10) . . . . ?
N3 C7 C8 N1 0.43(13) . . . . ?
C9 C7 C8 N1 177.95(11) . . . . ?
N3 C7 C9 O2 102.10(13) . . . . ?
C8 C7 C9 O2 -75.10(16) . . . . ?
C7 C8 N1 N2 -0.33(12) . . . . ?
C7 C8 N1 C6 -177.46(10) . . . . ?
C1 C6 N1 C8 18.86(18) . . . . ?
C5 C6 N1 C8 -163.08(11) . . . . ?
C1 C6 N1 N2 -158.07(10) . . . . ?
C5 C6 N1 N2 19.99(15) . . . . ?
C8 N1 N2 N3 0.11(12) . . . . ?
C6 N1 N2 N3 177.64(9) . . . . ?
N1 N2 N3 C7 0.17(13) . . . . ?
C8 C7 N3 N2 -0.38(14) . . . . ?
C9 C7 N3 N2 -178.11(10) . . . . ?



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 O2 0.82 1.87 2.6873(11) 175.4 2_557
O2 H2A N3 0.82 2.03 2.8357(13) 169.0 2_546



_diffrn_measured_fraction_theta_max 0.653

_diffrn_reflns_theta_full        25.00

_diffrn_measured_fraction_theta_full 0.960

_refine_diff_density_max         0.277

_refine_diff_density_min         -0.205

_refine_diff_density_rms         0.039
_database_code_depnum_ccdc_archive 'CCDC 924856'
#######################################################################
#
#                 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_new2
#TrackingRef 'sankararaman_81.cif'




_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;

?

;

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         'C10 H7 N3 O4'

_chemical_formula_sum            'C10 H7 N3 O4'

_chemical_formula_weight         233.19



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

_symmetry_space_group_name_Hall  '-P 2yn '

loop_

_symmetry_equiv_pos_as_xyz




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



_cell_length_a                   5.0172(11)

_cell_length_b                   9.3768(19)

_cell_length_c                   21.357(4)

_cell_angle_alpha                90.00

_cell_angle_beta                 96.602(10)

_cell_angle_gamma                90.00

_cell_volume                     998.1(4)

_cell_formula_units_Z            4

_cell_measurement_temperature    298(2)

_cell_measurement_reflns_used    1334

_cell_measurement_theta_min      2.90

_cell_measurement_theta_max      22.73



_exptl_crystal_description       Square

_exptl_crystal_colour            colourless

_exptl_crystal_size_max          0.25

_exptl_crystal_size_mid          0.20

_exptl_crystal_size_min          0.10

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    1.552

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             480

_exptl_absorpt_coefficient_mu    0.124

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.9698

_exptl_absorpt_correction_T_max  0.9878

_exptl_absorpt_process_details   'SADABS (Bruker,2004)'



_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 APEXII CCD area detector'

_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean ?

_diffrn_standards_number         ?

_diffrn_standards_interval_count ?

_diffrn_standards_interval_time  ?

_diffrn_standards_decay_%        ?

_diffrn_reflns_number            6029

_diffrn_reflns_av_R_equivalents  0.0382

_diffrn_reflns_av_sigmaI/netI    0.0477

_diffrn_reflns_limit_h_min       -5

_diffrn_reflns_limit_h_max       5

_diffrn_reflns_limit_k_min       -10

_diffrn_reflns_limit_k_max       11

_diffrn_reflns_limit_l_min       -25

_diffrn_reflns_limit_l_max       25

_diffrn_reflns_theta_min         1.92

_diffrn_reflns_theta_max         25.00

_reflns_number_total             1729

_reflns_number_gt                1215

_reflns_threshold_expression     >2sigma(I)



_computing_data_collection       'APEXII, Bruker,2004'
_computing_cell_refinement       'APEXII/SAINT, Bruker,2004'
_computing_data_reduction        'SAINT PLUS/XPREP, Bruker,2004'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'




_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)+(0.0456P)²+0.9243P] 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         1729

_refine_ls_number_parameters     162

_refine_ls_number_restraints     0

_refine_ls_R_factor_all          0.0865

_refine_ls_R_factor_gt           0.0546

_refine_ls_wR_factor_ref         0.1308

_refine_ls_wR_factor_gt          0.1173

_refine_ls_goodness_of_fit_ref   1.074

_refine_ls_restrained_S_all      1.074

_refine_ls_shift/su_max          0.000

_refine_ls_shift/su_mean         0.000



loop_

_atom_site_label

_atom_site_type_symbol

_atom_site_fract_x

_atom_site_fract_y

_atom_site_fract_z

_atom_site_U_iso_or_equiv

_atom_site_adp_type

_atom_site_occupancy

_atom_site_symmetry_multiplicity

_atom_site_calc_flag

_atom_site_refinement_flags

_atom_site_disorder_assembly

_atom_site_disorder_group
























C1 C 0.2856(6) 0.8875(3) 0.18132(12) 0.0263(7) Uani 1 1 d . . .
C2 C 0.4699(6) 0.7964(3) 0.15976(14) 0.0354(8) Uani 1 1 d . . .
H2 H 0.5746 0.7378 0.1878 0.042 Uiso 1 1 calc R . .
C3 C 0.4984(7) 0.7925(4) 0.09599(15) 0.0425(9) Uani 1 1 d . . .
H3 H 0.6213 0.7304 0.0811 0.051 Uiso 1 1 calc R . .
C4 C 0.3451(7) 0.8805(4) 0.05467(14) 0.0414(9) Uani 1 1 d . . .
H4 H 0.3635 0.8780 0.0118 0.050 Uiso 1 1 calc R . .
C5 C 0.1639(6) 0.9724(4) 0.07732(14) 0.0365(8) Uani 1 1 d . . .
H5 H 0.0630 1.0326 0.0492 0.044 Uiso 1 1 calc R . .
C6 C 0.1272(6) 0.9778(3) 0.14096(13) 0.0277(7) Uani 1 1 d . . .
C7 C -0.0779(6) 1.0750(3) 0.16375(13) 0.0285(7) Uani 1 1 d . . .
C8 C 0.2892(6) 0.9104(3) 0.34804(13) 0.0289(7) Uani 1 1 d . . .
C9 C 0.3999(6) 0.9537(3) 0.29549(13) 0.0300(7) Uani 1 1 d . . .
H9 H 0.5412 1.0170 0.2933 0.036 Uiso 1 1 calc R . .
C10 C 0.3765(7) 0.9485(4) 0.41389(14) 0.0385(8) Uani 1 1 d . . .
N1 N 0.2594(5) 0.8845(3) 0.24811(10) 0.0272(6) Uani 1 1 d . . .
N2 N 0.0694(5) 0.8005(3) 0.26918(11) 0.0348(7) Uani 1 1 d . . .
N3 N 0.0892(5) 0.8164(3) 0.33040(11) 0.0316(6) Uani 1 1 d . . .
O1 O -0.2151(5) 1.1481(3) 0.11745(10) 0.0412(6) Uani 1 1 d . . .
O2 O -0.1161(4) 1.0868(2) 0.21826(10) 0.0421(6) Uani 1 1 d . . .
O3 O 0.5680(5) 1.0299(3) 0.42672(10) 0.0572(8) Uani 1 1 d . . .
O4 O 0.2419(5) 0.8916(3) 0.45573(11) 0.0595(8) Uani 1 1 d . . .
H1O H -0.348(8) 1.209(5) 0.1345(19) 0.082(14) Uiso 1 1 d . . .
H2O H 0.318(11) 0.928(6) 0.499(3) 0.16(2) 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

















C1 0.0308(16) 0.0293(17) 0.0192(15) 0.0000(12) 0.0051(12) -0.0037(15)
C2 0.0386(19) 0.0369(19) 0.0309(17) 0.0050(15) 0.0048(14) 0.0095(16)
C3 0.046(2) 0.048(2) 0.0355(19) -0.0028(16) 0.0128(15) 0.0147(18)
C4 0.050(2) 0.055(2) 0.0213(16) -0.0032(16) 0.0103(15) 0.0104(19)
C5 0.044(2) 0.043(2) 0.0219(16) -0.0010(14) 0.0007(14) 0.0096(17)
C6 0.0303(16) 0.0319(17) 0.0210(15) -0.0022(13) 0.0041(12) 0.0002(14)
C7 0.0298(17) 0.0316(18) 0.0238(17) -0.0034(13) 0.0013(13) -0.0027(15)
C8 0.0322(17) 0.0321(18) 0.0217(15) 0.0009(13) 0.0007(12) -0.0043(15)
C9 0.0305(17) 0.0359(18) 0.0236(16) 0.0041(13) 0.0029(13) -0.0070(15)
C10 0.046(2) 0.045(2) 0.0241(17) 0.0026(15) 0.0042(15) -0.0078(18)
N1 0.0295(13) 0.0328(14) 0.0192(12) -0.0001(11) 0.0016(10) -0.0039(12)
N2 0.0353(15) 0.0435(16) 0.0263(14) 0.0021(12) 0.0068(11) -0.0128(14)
N3 0.0344(14) 0.0396(15) 0.0210(13) -0.0002(11) 0.0035(10) -0.0079(13)
O1 0.0440(14) 0.0514(16) 0.0283(12) 0.0011(11) 0.0039(10) 0.0219(13)
O2 0.0498(14) 0.0526(15) 0.0249(12) -0.0036(10) 0.0081(10) 0.0140(12)
O3 0.0683(17) 0.0741(19) 0.0279(13) -0.0031(12) 0.0006(12) -0.0418(16)
O4 0.0704(18) 0.086(2) 0.0232(13) -0.0017(13) 0.0084(12) -0.0387(16)



_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 C2 1.377(4) . ?
C1 C6 1.390(4) . ?
C1 N1 1.448(3) . ?
C2 C3 1.386(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.377(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.380(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.393(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.497(4) . ?
C7 O2 1.206(3) . ?
C7 O1 1.328(3) . ?
C8 N3 1.356(4) . ?
C8 C9 1.370(4) . ?
C8 C10 1.468(4) . ?
C9 N1 1.333(4) . ?
C9 H9 0.9300 . ?
C10 O3 1.233(4) . ?
C10 O4 1.295(4) . ?
N1 N2 1.353(3) . ?
N2 N3 1.308(3) . ?
O1 H1O 0.98(4) . ?
O4 H2O 1.01(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





































C2 C1 C6 121.9(3) . . ?
C2 C1 N1 117.2(2) . . ?
C6 C1 N1 120.8(3) . . ?
C1 C2 C3 119.6(3) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C4 C3 C2 120.0(3) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 119.5(3) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C4 C5 C6 122.1(3) . . ?
C4 C5 H5 119.0 . . ?
C6 C5 H5 119.0 . . ?
C1 C6 C5 116.9(3) . . ?
C1 C6 C7 122.3(3) . . ?
C5 C6 C7 120.8(3) . . ?
O2 C7 O1 123.0(3) . . ?
O2 C7 C6 124.1(3) . . ?
O1 C7 C6 112.9(2) . . ?
N3 C8 C9 108.8(3) . . ?
N3 C8 C10 123.6(3) . . ?
C9 C8 C10 127.5(3) . . ?
N1 C9 C8 104.4(3) . . ?
N1 C9 H9 127.8 . . ?
C8 C9 H9 127.8 . . ?
O3 C10 O4 123.8(3) . . ?
O3 C10 C8 120.1(3) . . ?
O4 C10 C8 116.0(3) . . ?
C9 N1 N2 111.2(2) . . ?
C9 N1 C1 129.7(3) . . ?
N2 N1 C1 119.1(2) . . ?
N3 N2 N1 106.9(2) . . ?
N2 N3 C8 108.7(2) . . ?
C7 O1 H1O 110(2) . . ?
C10 O4 H2O 108(3) . . ?



loop_

_geom_torsion_atom_site_label_1

_geom_torsion_atom_site_label_2

_geom_torsion_atom_site_label_3

_geom_torsion_atom_site_label_4

_geom_torsion

_geom_torsion_site_symmetry_1

_geom_torsion_site_symmetry_2

_geom_torsion_site_symmetry_3

_geom_torsion_site_symmetry_4

_geom_torsion_publ_flag
































C6 C1 C2 C3 -0.7(5) . . . . ?
N1 C1 C2 C3 178.4(3) . . . . ?
C1 C2 C3 C4 0.7(5) . . . . ?
C2 C3 C4 C5 0.1(5) . . . . ?
C3 C4 C5 C6 -1.0(5) . . . . ?
C2 C1 C6 C5 -0.2(4) . . . . ?
N1 C1 C6 C5 -179.3(3) . . . . ?
C2 C1 C6 C7 178.6(3) . . . . ?
N1 C1 C6 C7 -0.4(4) . . . . ?
C4 C5 C6 C1 1.0(5) . . . . ?
C4 C5 C6 C7 -177.8(3) . . . . ?
C1 C6 C7 O2 2.7(5) . . . . ?
C5 C6 C7 O2 -178.6(3) . . . . ?
C1 C6 C7 O1 -177.4(3) . . . . ?
C5 C6 C7 O1 1.4(4) . . . . ?
N3 C8 C9 N1 0.6(3) . . . . ?
C10 C8 C9 N1 176.7(3) . . . . ?
N3 C8 C10 O3 176.7(3) . . . . ?
C9 C8 C10 O3 1.1(5) . . . . ?
N3 C8 C10 O4 -3.2(5) . . . . ?
C9 C8 C10 O4 -178.7(3) . . . . ?
C8 C9 N1 N2 -0.4(3) . . . . ?
C8 C9 N1 C1 -179.9(3) . . . . ?
C2 C1 N1 C9 85.5(4) . . . . ?
C6 C1 N1 C9 -95.3(4) . . . . ?
C2 C1 N1 N2 -93.9(3) . . . . ?
C6 C1 N1 N2 85.2(3) . . . . ?
C9 N1 N2 N3 0.0(3) . . . . ?
C1 N1 N2 N3 179.6(2) . . . . ?
N1 N2 N3 C8 0.4(3) . . . . ?
C9 C8 N3 N2 -0.6(3) . . . . ?
C10 C8 N3 N2 -176.9(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



O4 H2O O3 1.01(6) 1.68(6) 2.684(3) 173(5) 3_676
O1 H1O N2 0.98(4) 2.59(4) 3.472(3) 149(3) 2_455
O1 H1O N3 0.98(4) 1.80(4) 2.781(3) 177(4) 2_455



_diffrn_measured_fraction_theta_max 0.991

_diffrn_reflns_theta_full        25.00

_diffrn_measured_fraction_theta_full 0.991

_refine_diff_density_max         0.200

_refine_diff_density_min         -0.236

_refine_diff_density_rms         0.053
_database_code_depnum_ccdc_archive 'CCDC 924857'
#######################################################################
#
#                 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_new3
#TrackingRef 'sankararaman_TZ.cif'




_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;

?

;

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         'C10 H9 N3 O3'

_chemical_formula_sum            'C10 H9 N3 O3'

_chemical_formula_weight         219.20



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           Orthorhombic

_symmetry_space_group_name_H-M   P2(1)2(1)2(1)
_symmetry_space_group_name_Hall  'P 2ac 2ab '


loop_

_symmetry_equiv_pos_as_xyz




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



_cell_length_a                   5.2611(2)

_cell_length_b                   9.6714(4)

_cell_length_c                   19.3615(8)

_cell_angle_alpha                90.00

_cell_angle_beta                 90.00

_cell_angle_gamma                90.00

_cell_volume                     985.16(7)

_cell_formula_units_Z            4

_cell_measurement_temperature    298(2)

_cell_measurement_reflns_used    3086

_cell_measurement_theta_min      2.35

_cell_measurement_theta_max      28.40



_exptl_crystal_description       Rectangular

_exptl_crystal_colour            colourless

_exptl_crystal_size_max          0.35

_exptl_crystal_size_mid          0.20

_exptl_crystal_size_min          0.15

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    1.478

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             456

_exptl_absorpt_coefficient_mu    0.112

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.9617

_exptl_absorpt_correction_T_max  0.9833

_exptl_absorpt_process_details   'SADABS (Bruker,2004)'



_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 APEXII CCD area detector'

_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean ?

_diffrn_standards_number         ?

_diffrn_standards_interval_count ?

_diffrn_standards_interval_time  ?

_diffrn_standards_decay_%        ?

_diffrn_reflns_number            3807

_diffrn_reflns_av_R_equivalents  0.0146

_diffrn_reflns_av_sigmaI/netI    0.0185

_diffrn_reflns_limit_h_min       -6

_diffrn_reflns_limit_h_max       5

_diffrn_reflns_limit_k_min       -11

_diffrn_reflns_limit_k_max       12

_diffrn_reflns_limit_l_min       -16

_diffrn_reflns_limit_l_max       25

_diffrn_reflns_theta_min         2.10

_diffrn_reflns_theta_max         28.40

_reflns_number_total             1871

_reflns_number_gt                1773

_reflns_threshold_expression     >2sigma(I)


_computing_data_collection       'APEXII, Bruker,2004'
_computing_cell_refinement       'APEXII/SAINT, Bruker,2004'
_computing_data_reduction        'SAINT PLUS/XPREP, Bruker,2004'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'




_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)+(0.0441P)²+0.1387P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'

_refine_ls_abs_structure_Flack   -0.2(12)

_refine_ls_number_reflns         1871

_refine_ls_number_parameters     153

_refine_ls_number_restraints     0

_refine_ls_R_factor_all          0.0316

_refine_ls_R_factor_gt           0.0295

_refine_ls_wR_factor_ref         0.0767

_refine_ls_wR_factor_gt          0.0745

_refine_ls_goodness_of_fit_ref   1.067

_refine_ls_restrained_S_all      1.067

_refine_ls_shift/su_max          0.000

_refine_ls_shift/su_mean         0.000



loop_

_atom_site_label

_atom_site_type_symbol

_atom_site_fract_x

_atom_site_fract_y

_atom_site_fract_z

_atom_site_U_iso_or_equiv

_atom_site_adp_type

_atom_site_occupancy

_atom_site_symmetry_multiplicity

_atom_site_calc_flag

_atom_site_refinement_flags

_atom_site_disorder_assembly

_atom_site_disorder_group

























C1 C 0.5239(3) 0.93192(15) 0.87925(7) 0.0265(3) Uani 1 1 d . . .
C2 C 0.6681(3) 0.93871(15) 0.93979(7) 0.0315(3) Uani 1 1 d . . .
H2 H 0.6352 1.0085 0.9716 0.038 Uiso 1 1 calc R . .
C3 C 0.8587(3) 0.84398(17) 0.95346(7) 0.0352(3) Uani 1 1 d . . .
H3 H 0.9541 0.8517 0.9937 0.042 Uiso 1 1 calc R . .
C4 C 0.9076(3) 0.73821(17) 0.90765(8) 0.0374(4) Uani 1 1 d . . .
H4 H 1.0330 0.6733 0.9174 0.045 Uiso 1 1 calc R . .
C5 C 0.7685(3) 0.72904(16) 0.84680(8) 0.0335(3) Uani 1 1 d . . .
H5 H 0.8014 0.6582 0.8156 0.040 Uiso 1 1 calc R . .
C6 C 0.5812(3) 0.82524(14) 0.83270(6) 0.0260(3) Uani 1 1 d . . .
C7 C 0.2955(3) 0.81951(15) 0.66526(7) 0.0304(3) Uani 1 1 d . . .
C8 C 0.4614(3) 0.88149(15) 0.70929(7) 0.0319(3) Uani 1 1 d . . .
H8 H 0.5626 0.9584 0.7006 0.038 Uiso 1 1 calc R . .
C9 C 0.3172(3) 1.03666(14) 0.87177(7) 0.0286(3) Uani 1 1 d . . .
C10 C 0.2191(3) 0.85367(18) 0.59247(8) 0.0404(4) Uani 1 1 d . . .
H10A H 0.3189 0.9315 0.5763 0.048 Uiso 1 1 calc R . .
H10B H 0.2559 0.7753 0.5629 0.048 Uiso 1 1 calc R . .
N1 N 0.4478(2) 0.80771(12) 0.76821(6) 0.0259(2) Uani 1 1 d . . .
N2 N 0.2835(2) 0.70304(12) 0.76216(6) 0.0304(3) Uani 1 1 d . . .
N3 N 0.1911(2) 0.71072(13) 0.69927(6) 0.0327(3) Uani 1 1 d . . .
O1 O 0.2837(2) 1.12516(13) 0.91506(6) 0.0488(3) Uani 1 1 d . . .
O2 O 0.1771(2) 1.02501(13) 0.81636(6) 0.0432(3) Uani 1 1 d . . .
O3 O -0.0420(3) 0.88656(14) 0.58749(7) 0.0495(3) Uani 1 1 d . . .
H1O H 0.057(5) 1.088(3) 0.8167(13) 0.084(8) Uiso 1 1 d . . .
H2O H -0.120(6) 0.807(3) 0.5852(14) 0.100(10) 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
















C1 0.0269(7) 0.0259(6) 0.0266(6) 0.0012(5) 0.0019(5) -0.0021(5)
C2 0.0368(8) 0.0323(7) 0.0253(6) -0.0019(5) -0.0004(5) -0.0005(7)
C3 0.0341(8) 0.0432(9) 0.0283(7) 0.0035(6) -0.0065(6) -0.0025(7)
C4 0.0324(7) 0.0393(8) 0.0406(8) 0.0050(6) -0.0037(7) 0.0079(7)
C5 0.0321(7) 0.0329(7) 0.0355(7) -0.0023(6) 0.0013(6) 0.0028(7)
C6 0.0257(6) 0.0277(7) 0.0246(6) 0.0005(5) -0.0002(5) -0.0036(6)
C7 0.0355(7) 0.0292(7) 0.0266(6) -0.0013(5) 0.0010(6) 0.0003(6)
C8 0.0385(8) 0.0292(7) 0.0280(6) 0.0011(6) 0.0005(6) -0.0056(7)
C9 0.0310(7) 0.0269(7) 0.0278(6) 0.0011(5) 0.0018(5) -0.0001(6)
C10 0.0501(9) 0.0431(9) 0.0280(7) 0.0026(6) -0.0035(7) -0.0062(8)
N1 0.0277(6) 0.0247(6) 0.0254(5) -0.0019(4) -0.0004(4) -0.0014(5)
N2 0.0311(6) 0.0297(6) 0.0304(6) 0.0013(5) -0.0036(5) -0.0061(5)
N3 0.0364(6) 0.0327(6) 0.0290(6) 0.0003(5) -0.0043(5) -0.0068(6)
O1 0.0545(7) 0.0457(6) 0.0463(6) -0.0177(5) -0.0127(6) 0.0191(6)
O2 0.0457(7) 0.0482(7) 0.0357(5) -0.0082(5) -0.0118(5) 0.0215(6)
O3 0.0542(7) 0.0448(7) 0.0496(7) 0.0160(6) -0.0160(6) -0.0038(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


























C1 C2 1.3977(19) . ?
C1 C6 1.4028(19) . ?
C1 C9 1.493(2) . ?
C2 C3 1.384(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.378(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.390(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.382(2) . ?
C5 H5 0.9300 . ?
C6 N1 1.4422(16) . ?
C7 N3 1.3575(19) . ?
C7 C8 1.359(2) . ?
C7 C10 1.502(2) . ?
C8 N1 1.3476(18) . ?
C8 H8 0.9300 . ?
C9 O1 1.2109(17) . ?
C9 O2 1.3066(17) . ?
C10 O3 1.414(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
N1 N2 1.3365(17) . ?
N2 N3 1.3132(16) . ?
O2 H1O 0.88(3) . ?
O3 H2O 0.87(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








































C2 C1 C6 117.18(13) . . ?
C2 C1 C9 116.41(12) . . ?
C6 C1 C9 126.38(12) . . ?
C3 C2 C1 121.50(13) . . ?
C3 C2 H2 119.2 . . ?
C1 C2 H2 119.2 . . ?
C4 C3 C2 120.24(13) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 119.65(14) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C6 C5 C4 119.99(13) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C1 121.42(12) . . ?
C5 C6 N1 116.01(12) . . ?
C1 C6 N1 122.56(12) . . ?
N3 C7 C8 107.31(12) . . ?
N3 C7 C10 121.14(13) . . ?
C8 C7 C10 131.54(14) . . ?
N1 C8 C7 105.28(13) . . ?
N1 C8 H8 127.4 . . ?
C7 C8 H8 127.4 . . ?
O1 C9 O2 123.17(13) . . ?
O1 C9 C1 121.22(13) . . ?
O2 C9 C1 115.61(12) . . ?
O3 C10 C7 111.94(14) . . ?
O3 C10 H10A 109.2 . . ?
C7 C10 H10A 109.2 . . ?
O3 C10 H10B 109.2 . . ?
C7 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
N2 N1 C8 111.17(11) . . ?
N2 N1 C6 118.67(10) . . ?
C8 N1 C6 130.16(11) . . ?
N3 N2 N1 106.14(11) . . ?
N2 N3 C7 110.11(12) . . ?
C9 O2 H1O 109.9(16) . . ?
C10 O3 H2O 105(2) . . ?



loop_

_geom_torsion_atom_site_label_1

_geom_torsion_atom_site_label_2

_geom_torsion_atom_site_label_3

_geom_torsion_atom_site_label_4

_geom_torsion

_geom_torsion_site_symmetry_1

_geom_torsion_site_symmetry_2

_geom_torsion_site_symmetry_3

_geom_torsion_site_symmetry_4

_geom_torsion_publ_flag






























C6 C1 C2 C3 -0.3(2) . . . . ?
C9 C1 C2 C3 177.68(13) . . . . ?
C1 C2 C3 C4 -1.2(2) . . . . ?
C2 C3 C4 C5 1.5(2) . . . . ?
C3 C4 C5 C6 -0.4(2) . . . . ?
C4 C5 C6 C1 -1.1(2) . . . . ?
C4 C5 C6 N1 179.73(13) . . . . ?
C2 C1 C6 C5 1.4(2) . . . . ?
C9 C1 C6 C5 -176.29(13) . . . . ?
C2 C1 C6 N1 -179.49(12) . . . . ?
C9 C1 C6 N1 2.8(2) . . . . ?
N3 C7 C8 N1 -0.48(17) . . . . ?
C10 C7 C8 N1 178.53(16) . . . . ?
C2 C1 C9 O1 2.4(2) . . . . ?
C6 C1 C9 O1 -179.85(14) . . . . ?
C2 C1 C9 O2 -177.07(13) . . . . ?
C6 C1 C9 O2 0.7(2) . . . . ?
N3 C7 C10 O3 61.5(2) . . . . ?
C8 C7 C10 O3 -117.42(19) . . . . ?
C7 C8 N1 N2 0.51(16) . . . . ?
C7 C8 N1 C6 179.90(13) . . . . ?
C5 C6 N1 N2 72.15(16) . . . . ?
C1 C6 N1 N2 -107.00(15) . . . . ?
C5 C6 N1 C8 -107.20(16) . . . . ?
C1 C6 N1 C8 73.7(2) . . . . ?
C8 N1 N2 N3 -0.34(15) . . . . ?
C6 N1 N2 N3 -179.80(12) . . . . ?
N1 N2 N3 C7 0.02(16) . . . . ?
C8 C7 N3 N2 0.30(18) . . . . ?
C10 C7 N3 N2 -178.83(14) . . . . ?



loop_

_geom_hbond_atom_site_label_D

_geom_hbond_atom_site_label_H

_geom_hbond_atom_site_label_A

_geom_hbond_distance_DH

_geom_hbond_distance_HA

_geom_hbond_distance_DA

_geom_hbond_angle_DHA

_geom_hbond_site_symmetry_A



O2 H1O N3 0.88(3) 1.79(3) 2.6587(17) 169(2) 3_556
O2 H1O N2 0.88(3) 2.60(3) 3.3386(16) 142(2) 3_556
O3 H2O O1 0.87(3) 1.96(3) 2.8303(19) 176(3) 3_546



_diffrn_measured_fraction_theta_max 0.876

_diffrn_reflns_theta_full        25.00

_diffrn_measured_fraction_theta_full 0.990

_refine_diff_density_max         0.147

_refine_diff_density_min         -0.185

_refine_diff_density_rms         0.037




_database_code_depnum_ccdc_archive 'CCDC 924858'
#######################################################################
#
#                 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_new



_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;

 ?

;

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         'C9 H7 N3 O3'

_chemical_formula_sum            
'C9 H7 N3 O3'

_chemical_formula_weight         205.18



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                   14.5117(7)

_cell_length_b                   5.1416(2)

_cell_length_c                   12.3092(6)

_cell_angle_alpha                90.00

_cell_angle_beta                 107.607(2)

_cell_angle_gamma                90.00

_cell_volume                     875.41(7)

_cell_formula_units_Z            4

_cell_measurement_temperature    298(2)

_cell_measurement_reflns_used    2450

_cell_measurement_theta_min      2.95

_cell_measurement_theta_max      31.59



_exptl_crystal_description       Rectangular

_exptl_crystal_colour            colourless

_exptl_crystal_size_max          0.25

_exptl_crystal_size_mid          0.15

_exptl_crystal_size_min          0.10

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    1.557

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             424

_exptl_absorpt_coefficient_mu    0.121

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.9704

_exptl_absorpt_correction_T_max  0.9880

_exptl_absorpt_process_details   ' SADABS (Bruker,2004)'



_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 APEXII CCD area detector'

_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean ?

_diffrn_standards_number         ?

_diffrn_standards_interval_count ?

_diffrn_standards_interval_time  ?

_diffrn_standards_decay_%        ?

_diffrn_reflns_number            5304

_diffrn_reflns_av_R_equivalents  0.0170

_diffrn_reflns_av_sigmaI/netI    0.0172

_diffrn_reflns_limit_h_min       -16

_diffrn_reflns_limit_h_max       17

_diffrn_reflns_limit_k_min       -5

_diffrn_reflns_limit_k_max       5

_diffrn_reflns_limit_l_min       -14

_diffrn_reflns_limit_l_max       14

_diffrn_reflns_theta_min         2.95

_diffrn_reflns_theta_max         25.00

_reflns_number_total             1521

_reflns_number_gt                1300

_reflns_threshold_expression     >2sigma(I)



_computing_data_collection       'APEXII, Bruker,2004'
_computing_cell_refinement       'APEXII/SAINT, Bruker,2004'
_computing_data_reduction        'SAINT PLUS/XPREP, Bruker,2004'
_computing_structure_solution    'SHELXS-97  (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97  (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3   (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97  (Sheldrick, 2008)'




_refine_special_details          
;

 Refinement of F² against ALL reflections.  The weighted R-factor wR and

 goodness of fit S are based on F², conventional R-factors R are based

 on F, with F set to zero for negative F². The threshold expression of

 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is

 not relevant to the choice of reflections for refinement.  R-factors based

 on F² are statistically about twice as large as those based on F, and R-

 factors based on ALL data will be even larger.

;



_refine_ls_structure_factor_coef Fsqd

_refine_ls_matrix_type           full

_refine_ls_weighting_scheme      calc

_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.1258P] 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         1521

_refine_ls_number_parameters     144

_refine_ls_number_restraints     1

_refine_ls_R_factor_all          0.0395

_refine_ls_R_factor_gt           0.0323

_refine_ls_wR_factor_ref         0.1186

_refine_ls_wR_factor_gt          0.1036

_refine_ls_goodness_of_fit_ref   0.907

_refine_ls_restrained_S_all      0.910

_refine_ls_shift/su_max          0.000

_refine_ls_shift/su_mean         0.000



loop_

_atom_site_label

_atom_site_type_symbol

_atom_site_fract_x

_atom_site_fract_y

_atom_site_fract_z

_atom_site_U_iso_or_equiv

_atom_site_adp_type

_atom_site_occupancy

_atom_site_symmetry_multiplicity

_atom_site_calc_flag

_atom_site_refinement_flags

_atom_site_disorder_assembly

_atom_site_disorder_group






















C1 C 0.12585(12) 0.8697(3) 0.28690(13) 0.0344(4) Uani 1 1 d . . .
H1 H 0.1193 0.9907 0.2289 0.041 Uiso 1 1 calc R . .
C2 C 0.06684(12) 0.8833(3) 0.35636(15) 0.0385(4) Uani 1 1 d . . .
H2 H 0.0203 1.0130 0.3456 0.046 Uiso 1 1 calc R . .
C3 C 0.07806(12) 0.7013(3) 0.44194(15) 0.0377(4) Uani 1 1 d . . .
H3 H 0.0386 0.7101 0.4889 0.045 Uiso 1 1 calc R . .
C4 C 0.14645(11) 0.5067(3) 0.45945(14) 0.0337(4) Uani 1 1 d . . .
H4 H 0.1523 0.3857 0.5173 0.040 Uiso 1 1 calc R . .
C5 C 0.20692(10) 0.4916(3) 0.39027(13) 0.0281(4) Uani 1 1 d . . .
C6 C 0.19451(10) 0.6760(3) 0.30404(12) 0.0278(4) Uani 1 1 d . . .
C7 C 0.35141(11) 0.7274(3) 0.13188(12) 0.0295(4) Uani 1 1 d . . .
C8 C 0.32207(11) 0.8270(3) 0.21885(13) 0.0301(4) Uani 1 1 d . . .
H8 H 0.3443 0.9767 0.2611 0.036 Uiso 1 1 calc R . .
C9 C 0.42076(11) 0.8338(3) 0.07802(14) 0.0333(4) Uani 1 1 d . . .
N1 N 0.25417(9) 0.6617(2) 0.22997(10) 0.0284(3) Uani 1 1 d . . .
N2 N 0.24084(10) 0.4653(2) 0.15304(11) 0.0351(4) Uani 1 1 d . . .
N3 N 0.30009(10) 0.5074(3) 0.09373(12) 0.0340(4) Uani 1 1 d . . .
O1 O 0.27786(8) 0.3130(2) 0.40321(10) 0.0367(3) Uani 1 1 d . . .
O2 O 0.46663(9) 1.0364(3) 0.12509(11) 0.0506(4) Uani 1 1 d D . .
O3 O 0.42943(9) 0.7273(2) -0.00979(10) 0.0442(4) Uani 1 1 d . . .
H1O H 0.2834(15) 0.216(4) 0.465(2) 0.061(6) Uiso 1 1 d . . .
H2O H 0.505(2) 1.109(8) 0.082(3) 0.177(17) Uiso 1 1 d 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















C1 0.0410(9) 0.0303(8) 0.0312(8) 0.0020(6) 0.0098(7) -0.0001(7)
C2 0.0367(9) 0.0345(9) 0.0461(10) -0.0029(8) 0.0152(7) 0.0034(7)
C3 0.0378(9) 0.0398(10) 0.0419(10) -0.0075(7) 0.0216(8) -0.0055(7)
C4 0.0400(9) 0.0330(9) 0.0319(9) 0.0017(6) 0.0166(7) -0.0057(7)
C5 0.0303(8) 0.0262(8) 0.0277(8) -0.0029(6) 0.0086(6) -0.0041(6)
C6 0.0327(8) 0.0276(8) 0.0245(8) -0.0029(6) 0.0111(6) -0.0048(6)
C7 0.0310(8) 0.0304(8) 0.0276(8) 0.0009(6) 0.0096(6) 0.0016(6)
C8 0.0341(8) 0.0297(8) 0.0267(8) -0.0008(6) 0.0095(6) -0.0043(6)
C9 0.0311(8) 0.0376(9) 0.0322(8) 0.0016(7) 0.0113(7) 0.0022(7)
N1 0.0366(7) 0.0262(7) 0.0247(6) -0.0017(5) 0.0130(5) -0.0026(5)
N2 0.0485(8) 0.0299(7) 0.0315(7) -0.0049(6) 0.0189(6) -0.0065(6)
N3 0.0427(8) 0.0318(8) 0.0312(7) -0.0026(5) 0.0166(6) -0.0012(6)
O1 0.0433(7) 0.0343(7) 0.0374(7) 0.0085(5) 0.0193(5) 0.0058(5)
O2 0.0512(8) 0.0610(9) 0.0461(8) -0.0136(6) 0.0246(6) -0.0222(6)
O3 0.0477(7) 0.0494(8) 0.0442(8) -0.0076(6) 0.0269(6) -0.0022(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























C1 C6 1.379(2) . ?
C1 C2 1.383(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.381(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.379(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.398(2) . ?
C4 H4 0.9300 . ?
C5 O1 1.3525(18) . ?
C5 C6 1.393(2) . ?
C6 N1 1.4364(18) . ?
C7 N3 1.358(2) . ?
C7 C8 1.366(2) . ?
C7 C9 1.468(2) . ?
C8 N1 1.3393(19) . ?
C8 H8 0.9300 . ?
C9 O3 1.2515(19) . ?
C9 O2 1.277(2) . ?
N1 N2 1.3576(18) . ?
N2 N3 1.3035(17) . ?
O1 H1O 0.89(2) . ?
O2 H2O 0.955(19) . ?



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 C1 C2 119.71(14) . . ?
C6 C1 H1 120.1 . . ?
C2 C1 H1 120.1 . . ?
C3 C2 C1 119.02(15) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C4 C3 C2 121.59(15) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C3 C4 C5 119.98(14) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
O1 C5 C6 118.03(13) . . ?
O1 C5 C4 124.18(14) . . ?
C6 C5 C4 117.78(13) . . ?
C1 C6 C5 121.91(13) . . ?
C1 C6 N1 119.07(13) . . ?
C5 C6 N1 119.01(13) . . ?
N3 C7 C8 108.37(13) . . ?
N3 C7 C9 122.23(14) . . ?
C8 C7 C9 129.29(15) . . ?
N1 C8 C7 104.81(13) . . ?
N1 C8 H8 127.6 . . ?
C7 C8 H8 127.6 . . ?
O3 C9 O2 125.02(14) . . ?
O3 C9 C7 119.28(15) . . ?
O2 C9 C7 115.68(14) . . ?
C8 N1 N2 110.78(12) . . ?
C8 N1 C6 129.48(12) . . ?
N2 N1 C6 119.64(11) . . ?
N3 N2 N1 106.76(11) . . ?
N2 N3 C7 109.29(13) . . ?
C5 O1 H1O 110.5(14) . . ?
C9 O2 H2O 112(3) . . ?



loop_

_geom_torsion_atom_site_label_1

_geom_torsion_atom_site_label_2

_geom_torsion_atom_site_label_3

_geom_torsion_atom_site_label_4

_geom_torsion

_geom_torsion_site_symmetry_1

_geom_torsion_site_symmetry_2

_geom_torsion_site_symmetry_3

_geom_torsion_site_symmetry_4

_geom_torsion_publ_flag




























C6 C1 C2 C3 0.0(2) . . . . ?
C1 C2 C3 C4 -0.1(2) . . . . ?
C2 C3 C4 C5 0.5(2) . . . . ?
C3 C4 C5 O1 177.90(14) . . . . ?
C3 C4 C5 C6 -0.7(2) . . . . ?
C2 C1 C6 C5 -0.3(2) . . . . ?
C2 C1 C6 N1 178.95(13) . . . . ?
O1 C5 C6 C1 -178.09(13) . . . . ?
C4 C5 C6 C1 0.6(2) . . . . ?
O1 C5 C6 N1 2.7(2) . . . . ?
C4 C5 C6 N1 -178.61(13) . . . . ?
N3 C7 C8 N1 0.22(17) . . . . ?
C9 C7 C8 N1 176.38(15) . . . . ?
N3 C7 C9 O3 4.0(2) . . . . ?
C8 C7 C9 O3 -171.69(15) . . . . ?
N3 C7 C9 O2 -177.54(14) . . . . ?
C8 C7 C9 O2 6.8(2) . . . . ?
C7 C8 N1 N2 -0.09(17) . . . . ?
C7 C8 N1 C6 -176.34(14) . . . . ?
C1 C6 N1 C8 67.0(2) . . . . ?
C5 C6 N1 C8 -113.72(16) . . . . ?
C1 C6 N1 N2 -108.92(16) . . . . ?
C5 C6 N1 N2 70.31(19) . . . . ?
C8 N1 N2 N3 -0.08(17) . . . . ?
C6 N1 N2 N3 176.59(12) . . . . ?
N1 N2 N3 C7 0.22(17) . . . . ?
C8 C7 N3 N2 -0.28(18) . . . . ?
C9 C7 N3 N2 -176.77(14) . . . . ?



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 H1O N3 0.89(2) 1.92(2) 2.8038(17) 177(2) 4_566
O2 H2O O3 0.955(19) 1.71(2) 2.6574(16) 173(4) 3_675



_diffrn_measured_fraction_theta_max 0.990

_diffrn_reflns_theta_full        25.00

_diffrn_measured_fraction_theta_full 0.990

_refine_diff_density_max         0.148

_refine_diff_density_min         -0.178

_refine_diff_density_rms         0.037

_database_code_depnum_ccdc_archive 'CCDC 936289'
#######################################################################
#
#                 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_new



_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;

 ?

;

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         'C15 H11 N3 O2'

_chemical_formula_sum            
'C15 H11 N3 O2'

_chemical_formula_weight         265.27



loop_

_atom_type_symbol

_atom_type_description

_atom_type_scat_dispersion_real

_atom_type_scat_dispersion_imag

_atom_type_scat_source








C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'



_symmetry_cell_setting           Orthorhombic

_symmetry_space_group_name_H-M   P2(1)2(1)2(1)



loop_

_symmetry_equiv_pos_as_xyz




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



_cell_length_a                   5.7364(2)

_cell_length_b                   11.9294(5)

_cell_length_c                   18.4660(9)

_cell_angle_alpha                90.00

_cell_angle_beta                 90.00

_cell_angle_gamma                90.00

_cell_volume                     1263.66(9)

_cell_formula_units_Z            4

_cell_measurement_temperature    298(2)

_cell_measurement_reflns_used    1396

_cell_measurement_theta_min      2.79

_cell_measurement_theta_max      22.35



_exptl_crystal_description       Square

_exptl_crystal_colour            colourless

_exptl_crystal_size_max          0.15

_exptl_crystal_size_mid          0.10

_exptl_crystal_size_min          0.06

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    1.394

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             552

_exptl_absorpt_coefficient_mu    0.096

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.9857

_exptl_absorpt_correction_T_max  0.9943

_exptl_absorpt_process_details   'SADABS (Bruker, 2004)'



_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 ApexII CCD area detector'

_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean ?

_diffrn_standards_number         ?

_diffrn_standards_interval_count ?

_diffrn_standards_interval_time  ?

_diffrn_standards_decay_%        ?

_diffrn_reflns_number            5076

_diffrn_reflns_av_R_equivalents  0.0240

_diffrn_reflns_av_sigmaI/netI    0.0501

_diffrn_reflns_limit_h_min       -7

_diffrn_reflns_limit_h_max       5

_diffrn_reflns_limit_k_min       -15

_diffrn_reflns_limit_k_max       10

_diffrn_reflns_limit_l_min       -15

_diffrn_reflns_limit_l_max       23

_diffrn_reflns_theta_min         2.03

_diffrn_reflns_theta_max         27.28

_reflns_number_total             2639

_reflns_number_gt                1915

_reflns_threshold_expression     >2sigma(I)


_computing_data_collection       'APEXII, Bruker,2004'
_computing_cell_refinement       'APEXII/SAINT, Bruker,2004'
_computing_data_reduction        'SAINT PLUS/XPREP, Bruker,2004'
_computing_structure_solution    'SHELXS-97  (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97  (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3   (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97  (Sheldrick, 2008)'




_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)+(0.0423P)²+0.0260P] 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_abs_structure_details 
'Flack H D (1983), Acta Cryst. A39, 876-881'

_refine_ls_abs_structure_Flack   -0.3(18)

_refine_ls_number_reflns         2639

_refine_ls_number_parameters     185

_refine_ls_number_restraints     0

_refine_ls_R_factor_all          0.0765

_refine_ls_R_factor_gt           0.0476

_refine_ls_wR_factor_ref         0.0973

_refine_ls_wR_factor_gt          0.0852

_refine_ls_goodness_of_fit_ref   1.043

_refine_ls_restrained_S_all      1.043

_refine_ls_shift/su_max          0.000

_refine_ls_shift/su_mean         0.000



loop_

_atom_site_label

_atom_site_type_symbol

_atom_site_fract_x

_atom_site_fract_y

_atom_site_fract_z

_atom_site_U_iso_or_equiv

_atom_site_adp_type

_atom_site_occupancy

_atom_site_symmetry_multiplicity

_atom_site_calc_flag

_atom_site_refinement_flags

_atom_site_disorder_assembly

_atom_site_disorder_group































C1 C 0.5297(4) 0.64328(19) 0.50306(12) 0.0427(6) Uani 1 1 d . . .
H1 H 0.6580 0.6769 0.5249 0.051 Uiso 1 1 calc R . .
C2 C 0.5220(4) 0.63318(19) 0.42850(12) 0.0466(6) Uani 1 1 d . . .
H2 H 0.6445 0.6606 0.4006 0.056 Uiso 1 1 calc R . .
C3 C 0.3358(4) 0.58323(19) 0.39540(12) 0.0457(6) Uani 1 1 d . . .
H3 H 0.3324 0.5755 0.3453 0.055 Uiso 1 1 calc R . .
C4 C 0.1535(5) 0.5446(2) 0.43689(12) 0.0492(6) Uani 1 1 d . . .
H4 H 0.0256 0.5114 0.4146 0.059 Uiso 1 1 calc R . .
C5 C 0.1590(4) 0.55471(19) 0.51168(12) 0.0431(6) Uani 1 1 d . . .
H5 H 0.0348 0.5283 0.5392 0.052 Uiso 1 1 calc R . .
C6 C 0.3480(4) 0.60386(17) 0.54566(11) 0.0319(5) Uani 1 1 d . . .
C7 C 0.3568(4) 0.61500(17) 0.62522(11) 0.0322(5) Uani 1 1 d . . .
C8 C 0.5142(4) 0.67187(18) 0.66722(11) 0.0363(5) Uani 1 1 d . . .
H8 H 0.6433 0.7123 0.6516 0.044 Uiso 1 1 calc R . .
C9 C 0.5452(4) 0.69813(18) 0.80173(11) 0.0325(5) Uani 1 1 d . . .
C10 C 0.7375(4) 0.64203(19) 0.82789(12) 0.0413(6) Uani 1 1 d . . .
H10 H 0.7995 0.5816 0.8025 0.050 Uiso 1 1 calc R . .
C11 C 0.8375(4) 0.6767(2) 0.89245(12) 0.0467(6) Uani 1 1 d . . .
H11 H 0.9691 0.6404 0.9101 0.056 Uiso 1 1 calc R . .
C12 C 0.7426(4) 0.76466(19) 0.93032(12) 0.0438(6) Uani 1 1 d . . .
H12 H 0.8078 0.7864 0.9742 0.053 Uiso 1 1 calc R . .
C13 C 0.5516(4) 0.82067(18) 0.90354(11) 0.0385(5) Uani 1 1 d . . .
H13 H 0.4900 0.8804 0.9297 0.046 Uiso 1 1 calc R . .
C14 C 0.4485(4) 0.79008(16) 0.83828(11) 0.0315(5) Uani 1 1 d . . .
C15 C 0.2533(4) 0.85768(19) 0.80793(11) 0.0382(5) Uani 1 1 d . . .
N1 N 0.1993(3) 0.56827(16) 0.67055(10) 0.0439(5) Uani 1 1 d . . .
N2 N 0.2507(3) 0.59314(16) 0.73814(9) 0.0453(5) Uani 1 1 d . . .
N3 N 0.4426(3) 0.65687(14) 0.73564(9) 0.0330(4) Uani 1 1 d . . .
O1 O 0.1631(3) 0.92580(16) 0.85662(9) 0.0547(5) Uani 1 1 d . . .
O2 O 0.1887(4) 0.85527(17) 0.74663(9) 0.0818(7) Uani 1 1 d . . .
H1O H 0.027(6) 0.974(3) 0.8382(16) 0.119(12) 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




















C1 0.0426(13) 0.0439(13) 0.0417(13) -0.0011(12) 0.0016(11) -0.0076(13)
C2 0.0531(15) 0.0472(14) 0.0394(13) 0.0015(12) 0.0098(13) -0.0012(13)
C3 0.0642(16) 0.0429(14) 0.0302(11) -0.0034(11) -0.0003(13) 0.0077(14)
C4 0.0521(14) 0.0550(16) 0.0405(13) -0.0050(13) -0.0123(13) -0.0053(14)
C5 0.0432(13) 0.0466(14) 0.0395(12) 0.0001(12) 0.0020(12) -0.0056(12)
C6 0.0369(11) 0.0264(11) 0.0323(11) -0.0005(10) 0.0032(10) 0.0035(11)
C7 0.0334(11) 0.0280(11) 0.0352(11) 0.0000(10) 0.0046(11) -0.0012(10)
C8 0.0351(12) 0.0380(12) 0.0356(11) 0.0007(11) 0.0045(11) -0.0083(11)
C9 0.0348(12) 0.0325(11) 0.0301(11) -0.0012(10) 0.0032(10) -0.0042(11)
C10 0.0368(12) 0.0374(12) 0.0497(13) -0.0068(12) 0.0021(12) 0.0018(12)
C11 0.0381(12) 0.0464(14) 0.0556(14) 0.0030(13) -0.0128(13) 0.0051(12)
C12 0.0482(13) 0.0431(13) 0.0401(12) -0.0017(11) -0.0122(12) -0.0035(14)
C13 0.0453(13) 0.0354(12) 0.0346(12) -0.0031(11) 0.0005(12) 0.0012(12)
C14 0.0357(11) 0.0284(11) 0.0304(11) 0.0052(10) 0.0028(10) 0.0000(10)
C15 0.0424(13) 0.0387(13) 0.0334(12) 0.0023(11) 0.0019(11) 0.0025(12)
N1 0.0415(12) 0.0547(12) 0.0354(10) -0.0040(10) 0.0029(9) -0.0180(10)
N2 0.0429(11) 0.0563(12) 0.0368(10) -0.0032(10) 0.0069(10) -0.0187(11)
N3 0.0340(10) 0.0343(10) 0.0309(9) -0.0030(9) 0.0045(8) -0.0045(9)
O1 0.0544(11) 0.0651(12) 0.0447(10) -0.0107(9) -0.0038(9) 0.0252(10)
O2 0.1098(17) 0.0966(15) 0.0389(9) -0.0094(10) -0.0240(11) 0.0585(15)



_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 C2 1.383(3) . ?
C1 C6 1.388(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.368(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.375(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.387(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.383(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.476(3) . ?
C7 N1 1.352(3) . ?
C7 C8 1.370(3) . ?
C8 N3 1.341(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.378(3) . ?
C9 C14 1.402(3) . ?
C9 N3 1.441(2) . ?
C10 C11 1.386(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.373(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.375(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.391(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.489(3) . ?
C15 O2 1.191(2) . ?
C15 O1 1.318(3) . ?
N1 N2 1.316(2) . ?
N2 N3 1.339(2) . ?
O1 H1O 1.02(4) . ?



loop_

_geom_angle_atom_site_label_1

_geom_angle_atom_site_label_2

_geom_angle_atom_site_label_3

_geom_angle

_geom_angle_site_symmetry_1

_geom_angle_site_symmetry_3

_geom_angle_publ_flag



















































C2 C1 C6 120.7(2) . . ?
C2 C1 H1 119.6 . . ?
C6 C1 H1 119.6 . . ?
C3 C2 C1 120.5(2) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 119.4(2) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C3 C4 C5 120.5(2) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C6 C5 C4 120.4(2) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C1 118.35(19) . . ?
C5 C6 C7 121.1(2) . . ?
C1 C6 C7 120.5(2) . . ?
N1 C7 C8 107.11(17) . . ?
N1 C7 C6 123.8(2) . . ?
C8 C7 C6 129.1(2) . . ?
N3 C8 C7 105.40(19) . . ?
N3 C8 H8 127.3 . . ?
C7 C8 H8 127.3 . . ?
C10 C9 C14 121.86(19) . . ?
C10 C9 N3 117.25(19) . . ?
C14 C9 N3 120.88(19) . . ?
C9 C10 C11 119.2(2) . . ?
C9 C10 H10 120.4 . . ?
C11 C10 H10 120.4 . . ?
C12 C11 C10 120.1(2) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C11 C12 C13 120.3(2) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C12 C13 C14 121.5(2) . . ?
C12 C13 H13 119.2 . . ?
C14 C13 H13 119.2 . . ?
C13 C14 C9 117.00(19) . . ?
C13 C14 C15 120.23(19) . . ?
C9 C14 C15 122.67(18) . . ?
O2 C15 O1 122.8(2) . . ?
O2 C15 C14 125.3(2) . . ?
O1 C15 C14 111.86(18) . . ?
N2 N1 C7 110.13(18) . . ?
N1 N2 N3 106.24(17) . . ?
N2 N3 C8 111.12(17) . . ?
N2 N3 C9 120.03(17) . . ?
C8 N3 C9 128.85(18) . . ?
C15 O1 H1O 114.6(17) . . ?



loop_

_geom_torsion_atom_site_label_1

_geom_torsion_atom_site_label_2

_geom_torsion_atom_site_label_3

_geom_torsion_atom_site_label_4

_geom_torsion

_geom_torsion_site_symmetry_1

_geom_torsion_site_symmetry_2

_geom_torsion_site_symmetry_3

_geom_torsion_site_symmetry_4

_geom_torsion_publ_flag








































C6 C1 C2 C3 -0.5(4) . . . . ?
C1 C2 C3 C4 1.1(4) . . . . ?
C2 C3 C4 C5 -0.8(4) . . . . ?
C3 C4 C5 C6 0.0(4) . . . . ?
C4 C5 C6 C1 0.5(3) . . . . ?
C4 C5 C6 C7 -179.8(2) . . . . ?
C2 C1 C6 C5 -0.3(3) . . . . ?
C2 C1 C6 C7 -179.9(2) . . . . ?
C5 C6 C7 N1 7.7(3) . . . . ?
C1 C6 C7 N1 -172.7(2) . . . . ?
C5 C6 C7 C8 -171.7(2) . . . . ?
C1 C6 C7 C8 7.9(4) . . . . ?
N1 C7 C8 N3 -0.3(2) . . . . ?
C6 C7 C8 N3 179.2(2) . . . . ?
C14 C9 C10 C11 0.5(3) . . . . ?
N3 C9 C10 C11 -178.07(19) . . . . ?
C9 C10 C11 C12 1.2(3) . . . . ?
C10 C11 C12 C13 -1.7(4) . . . . ?
C11 C12 C13 C14 0.4(3) . . . . ?
C12 C13 C14 C9 1.3(3) . . . . ?
C12 C13 C14 C15 -175.33(19) . . . . ?
C10 C9 C14 C13 -1.7(3) . . . . ?
N3 C9 C14 C13 176.81(19) . . . . ?
C10 C9 C14 C15 174.8(2) . . . . ?
N3 C9 C14 C15 -6.7(3) . . . . ?
C13 C14 C15 O2 162.0(3) . . . . ?
C9 C14 C15 O2 -14.4(4) . . . . ?
C13 C14 C15 O1 -15.3(3) . . . . ?
C9 C14 C15 O1 168.3(2) . . . . ?
C8 C7 N1 N2 0.0(2) . . . . ?
C6 C7 N1 N2 -179.5(2) . . . . ?
C7 N1 N2 N3 0.3(2) . . . . ?
N1 N2 N3 C8 -0.5(2) . . . . ?
N1 N2 N3 C9 -179.77(19) . . . . ?
C7 C8 N3 N2 0.5(2) . . . . ?
C7 C8 N3 C9 179.69(19) . . . . ?
C10 C9 N3 N2 100.6(2) . . . . ?
C14 C9 N3 N2 -78.0(2) . . . . ?
C10 C9 N3 C8 -78.6(3) . . . . ?
C14 C9 N3 C8 102.8(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


O1 H1O N2 1.02(4) 2.56(3) 3.561(3) 165(2) 3_556
O1 H1O N1 1.02(4) 1.73(4) 2.732(3) 165(3) 3_556



_diffrn_measured_fraction_theta_max 0.978

_diffrn_reflns_theta_full        25.00

_diffrn_measured_fraction_theta_full 0.997

_refine_diff_density_max         0.147

_refine_diff_density_min         -0.146

_refine_diff_density_rms         0.038

_database_code_depnum_ccdc_archive 'CCDC 936290'
#######################################################################
#
#                 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_new



_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;

 ?

;

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         'C10 H9 N3 O3'

_chemical_formula_sum            
'C10 H9 N3 O3'

_chemical_formula_weight         219.20



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                   5.5178(8)

_cell_length_b                   6.7350(10)

_cell_length_c                   13.337(2)

_cell_angle_alpha                87.308(6)

_cell_angle_beta                 82.823(6)

_cell_angle_gamma                74.791(6)

_cell_volume                     474.49(12)

_cell_formula_units_Z            2

_cell_measurement_temperature    298(2)

_cell_measurement_reflns_used    2463

_cell_measurement_theta_min      0.00

_cell_measurement_theta_max      0.00



_exptl_crystal_description       Block

_exptl_crystal_colour            colourless

_exptl_crystal_size_max          0.25

_exptl_crystal_size_mid          0.20

_exptl_crystal_size_min          0.15

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    1.534

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             228

_exptl_absorpt_coefficient_mu    0.117

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.9714

_exptl_absorpt_correction_T_max  0.9827

_exptl_absorpt_process_details   'SADABS (Bruker,2004)'



_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 APEXII CCD area detector'

_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean ?

_diffrn_standards_number         ?

_diffrn_standards_interval_count ?

_diffrn_standards_interval_time  ?

_diffrn_standards_decay_%        ?

_diffrn_reflns_number            4813

_diffrn_reflns_av_R_equivalents  0.0359

_diffrn_reflns_av_sigmaI/netI    0.0373

_diffrn_reflns_limit_h_min       -6

_diffrn_reflns_limit_h_max       6

_diffrn_reflns_limit_k_min       -8

_diffrn_reflns_limit_k_max       7

_diffrn_reflns_limit_l_min       -15

_diffrn_reflns_limit_l_max       15

_diffrn_reflns_theta_min         3.08

_diffrn_reflns_theta_max         25.00

_reflns_number_total             1568

_reflns_number_gt                1145

_reflns_threshold_expression     >2sigma(I)


_computing_data_collection       'APEXII, Bruker,2004'
_computing_cell_refinement       'APEXII/SAINT, Bruker,2004'
_computing_data_reduction        'SAINT PLUS/XPREP, Bruker,2004'
_computing_structure_solution    'SHELXS-97  (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97  (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3   (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97  (Sheldrick, 2008)'




_refine_special_details          
;

 Refinement of F² against ALL reflections.  The weighted R-factor wR and

 goodness of fit S are based on F², conventional R-factors R are based

 on F, with F set to zero for negative F². The threshold expression of

 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is

 not relevant to the choice of reflections for refinement.  R-factors based

 on F² are statistically about twice as large as those based on F, and R-

 factors based on ALL data will be even larger.

;



_refine_ls_structure_factor_coef Fsqd

_refine_ls_matrix_type           full

_refine_ls_weighting_scheme      calc

_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.2004P] 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         1568

_refine_ls_number_parameters     150

_refine_ls_number_restraints     0

_refine_ls_R_factor_all          0.0839

_refine_ls_R_factor_gt           0.0591

_refine_ls_wR_factor_ref         0.1933

_refine_ls_wR_factor_gt          0.1584

_refine_ls_goodness_of_fit_ref   1.178

_refine_ls_restrained_S_all      1.178

_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 0.2003(4) -0.4015(3) 0.41900(16) 0.0469(6) Uani 1 1 d . . .
O2 O -0.2057(4) -0.2621(3) 0.47331(16) 0.0480(7) Uani 1 1 d . . .
H2 H -0.1900 -0.3738 0.5026 0.072 Uiso 1 1 calc R . .
C2 C 0.0118(5) -0.0609(4) 0.36658(18) 0.0301(7) Uani 1 1 d . . .
C5 C 0.0339(5) 0.2932(4) 0.25762(19) 0.0318(7) Uani 1 1 d . . .
N2 N -0.1575(5) 0.6294(4) 0.1916(2) 0.0482(7) Uani 1 1 d . . .
C4 C 0.2446(6) 0.1297(4) 0.2542(2) 0.0378(7) Uani 1 1 d . . .
H4 H 0.3934 0.1385 0.2151 0.045 Uiso 1 1 calc R . .
C7 C -0.1974(6) 0.1054(4) 0.3708(2) 0.0346(7) Uani 1 1 d . . .
H7 H -0.3457 0.0970 0.4104 0.042 Uiso 1 1 calc R . .
N1 N 0.0475(5) 0.4745(4) 0.19861(17) 0.0370(7) Uani 1 1 d . . .
C6 C -0.1895(6) 0.2853(4) 0.3166(2) 0.0372(7) Uani 1 1 d . . .
H6 H -0.3303 0.3977 0.3198 0.045 Uiso 1 1 calc R . .
C1 C 0.0051(5) -0.2555(4) 0.42295(19) 0.0330(7) Uani 1 1 d . . .
C3 C 0.2347(6) -0.0482(4) 0.3090(2) 0.0363(7) Uani 1 1 d . . .
H3 H 0.3773 -0.1590 0.3073 0.044 Uiso 1 1 calc R . .
N3 N -0.0853(5) 0.7699(4) 0.1310(2) 0.0502(8) Uani 1 1 d . . .
C8 C 0.2518(6) 0.5155(5) 0.1438(2) 0.0431(8) Uani 1 1 d . . .
H8 H 0.4169 0.4331 0.1372 0.052 Uiso 1 1 calc R . .
C10 C 0.3066(7) 0.8261(5) 0.0317(2) 0.0521(9) Uani 1 1 d . . .
H10A H 0.2575 0.9676 0.0540 0.062 Uiso 1 1 calc R . .
H10B H 0.4867 0.7729 0.0351 0.062 Uiso 1 1 calc R . .
C9 C 0.1658(6) 0.7013(5) 0.1006(2) 0.0419(8) Uani 1 1 d . . .
O3 O 0.2557(5) 0.8203(4) -0.06948(17) 0.0580(7) Uani 1 1 d . . .
H1O H 0.213(9) 0.971(9) -0.093(3) 0.106(16) 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
















O1 0.0484(15) 0.0258(12) 0.0588(14) 0.0159(9) 0.0093(10) -0.0061(11)
O2 0.0446(14) 0.0329(13) 0.0621(14) 0.0213(10) 0.0094(10) -0.0130(11)
C2 0.0372(16) 0.0263(15) 0.0286(14) 0.0069(11) -0.0005(11) -0.0140(13)
C5 0.0419(17) 0.0252(15) 0.0315(14) 0.0112(11) -0.0024(11) -0.0172(14)
N2 0.0432(17) 0.0386(16) 0.0595(17) 0.0220(12) -0.0006(12) -0.0114(14)
C4 0.0395(18) 0.0324(17) 0.0413(16) 0.0100(12) 0.0065(12) -0.0158(15)
C7 0.0335(16) 0.0325(16) 0.0377(16) 0.0100(12) 0.0027(11) -0.0135(14)
N1 0.0426(15) 0.0272(13) 0.0417(14) 0.0148(10) -0.0032(10) -0.0136(12)
C6 0.0376(17) 0.0292(16) 0.0432(16) 0.0118(12) -0.0033(12) -0.0083(14)
C1 0.0403(18) 0.0255(16) 0.0338(15) 0.0068(11) 0.0006(12) -0.0130(15)
C3 0.0358(17) 0.0269(15) 0.0428(16) 0.0082(12) 0.0016(12) -0.0068(13)
N3 0.0517(18) 0.0394(16) 0.0580(17) 0.0270(12) -0.0051(13) -0.0146(14)
C8 0.0418(18) 0.0358(18) 0.0497(18) 0.0149(13) 0.0024(13) -0.0130(15)
C10 0.056(2) 0.048(2) 0.056(2) 0.0230(16) -0.0035(15) -0.0236(18)
C9 0.049(2) 0.0356(17) 0.0422(17) 0.0140(13) -0.0033(13) -0.0166(15)
O3 0.0690(18) 0.0460(15) 0.0504(14) 0.0198(11) 0.0048(11) -0.0088(13)



_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 1.251(3) . ?
O2 C1 1.278(3) . ?
O2 H2 0.8200 . ?
C2 C7 1.379(4) . ?
C2 C3 1.387(4) . ?
C2 C1 1.487(4) . ?
C5 C4 1.373(4) . ?
C5 C6 1.389(4) . ?
C5 N1 1.435(3) . ?
N2 N3 1.323(3) . ?
N2 N1 1.332(4) . ?
C4 C3 1.384(4) . ?
C4 H4 0.9300 . ?
C7 C6 1.389(4) . ?
C7 H7 0.9300 . ?
N1 C8 1.350(4) . ?
C6 H6 0.9300 . ?
C3 H3 0.9300 . ?
N3 C9 1.356(4) . ?
C8 C9 1.346(4) . ?
C8 H8 0.9300 . ?
C10 O3 1.417(4) . ?
C10 C9 1.499(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
O3 H1O 1.03(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








































C1 O2 H2 109.5 . . ?
C7 C2 C3 119.9(2) . . ?
C7 C2 C1 121.5(2) . . ?
C3 C2 C1 118.7(3) . . ?
C4 C5 C6 121.3(2) . . ?
C4 C5 N1 118.7(2) . . ?
C6 C5 N1 120.0(3) . . ?
N3 N2 N1 106.7(2) . . ?
C5 C4 C3 119.8(3) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C2 C7 C6 120.8(3) . . ?
C2 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
N2 N1 C8 110.8(2) . . ?
N2 N1 C5 121.1(2) . . ?
C8 N1 C5 128.1(3) . . ?
C7 C6 C5 118.4(3) . . ?
C7 C6 H6 120.8 . . ?
C5 C6 H6 120.8 . . ?
O1 C1 O2 123.8(2) . . ?
O1 C1 C2 119.6(2) . . ?
O2 C1 C2 116.6(3) . . ?
C4 C3 C2 119.8(3) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
N2 N3 C9 108.7(2) . . ?
C9 C8 N1 105.3(3) . . ?
C9 C8 H8 127.4 . . ?
N1 C8 H8 127.4 . . ?
O3 C10 C9 111.2(3) . . ?
O3 C10 H10A 109.4 . . ?
C9 C10 H10A 109.4 . . ?
O3 C10 H10B 109.4 . . ?
C9 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
C8 C9 N3 108.5(3) . . ?
C8 C9 C10 129.5(3) . . ?
N3 C9 C10 122.0(3) . . ?
C10 O3 H1O 105(3) . . ?



loop_

_geom_torsion_atom_site_label_1

_geom_torsion_atom_site_label_2

_geom_torsion_atom_site_label_3

_geom_torsion_atom_site_label_4

_geom_torsion

_geom_torsion_site_symmetry_1

_geom_torsion_site_symmetry_2

_geom_torsion_site_symmetry_3

_geom_torsion_site_symmetry_4

_geom_torsion_publ_flag





























C6 C5 C4 C3 1.1(4) . . . . ?
N1 C5 C4 C3 -178.8(2) . . . . ?
C3 C2 C7 C6 1.1(4) . . . . ?
C1 C2 C7 C6 -179.1(2) . . . . ?
N3 N2 N1 C8 0.7(3) . . . . ?
N3 N2 N1 C5 -178.7(2) . . . . ?
C4 C5 N1 N2 173.5(3) . . . . ?
C6 C5 N1 N2 -6.4(4) . . . . ?
C4 C5 N1 C8 -5.8(4) . . . . ?
C6 C5 N1 C8 174.3(3) . . . . ?
C2 C7 C6 C5 0.4(4) . . . . ?
C4 C5 C6 C7 -1.5(4) . . . . ?
N1 C5 C6 C7 178.4(2) . . . . ?
C7 C2 C1 O1 -178.5(2) . . . . ?
C3 C2 C1 O1 1.3(4) . . . . ?
C7 C2 C1 O2 1.6(4) . . . . ?
C3 C2 C1 O2 -178.6(2) . . . . ?
C5 C4 C3 C2 0.4(4) . . . . ?
C7 C2 C3 C4 -1.5(4) . . . . ?
C1 C2 C3 C4 178.7(2) . . . . ?
N1 N2 N3 C9 -0.1(3) . . . . ?
N2 N1 C8 C9 -1.0(3) . . . . ?
C5 N1 C8 C9 178.3(3) . . . . ?
N1 C8 C9 N3 0.9(3) . . . . ?
N1 C8 C9 C10 179.8(3) . . . . ?
N2 N3 C9 C8 -0.6(4) . . . . ?
N2 N3 C9 C10 -179.5(3) . . . . ?
O3 C10 C9 C8 105.1(4) . . . . ?
O3 C10 C9 N3 -76.2(4) . . . . ?



loop_

_geom_hbond_atom_site_label_D

_geom_hbond_atom_site_label_H

_geom_hbond_atom_site_label_A

_geom_hbond_distance_DH

_geom_hbond_distance_HA

_geom_hbond_distance_DA

_geom_hbond_angle_DHA

_geom_hbond_site_symmetry_A


O2 H2 O1 0.82 1.81 2.620(3) 170.5 2_546
O3 H1O N3 1.03(6) 1.78(6) 2.792(4) 170(4) 2_575



_diffrn_measured_fraction_theta_max 0.937

_diffrn_reflns_theta_full        25.00

_diffrn_measured_fraction_theta_full 0.937

_refine_diff_density_max         0.273

_refine_diff_density_min         -0.340

_refine_diff_density_rms         0.079

_database_code_depnum_ccdc_archive 'CCDC 936843'
