# 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_2_Y

_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H9 N3 O'
_chemical_formula_sum            'C14 H9 N3 O'
_chemical_formula_weight         235.24

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/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                   6.052(6)
_cell_length_b                   4.919(5)
_cell_length_c                   36.98(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.115(4)
_cell_angle_gamma                90.00
_cell_volume                     1098.0(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    8137
_cell_measurement_theta_min      3.3
_cell_measurement_theta_max      27.4

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             488
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9815
_exptl_absorpt_correction_T_max  0.9953
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71070
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Rotating anode'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_detector       CCD
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       dtprofit.ref
_diffrn_detector_area_resol_mean 14.7059
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8137
_diffrn_reflns_av_R_equivalents  0.1011
_diffrn_reflns_av_sigmaI/netI    0.0977
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_theta_min         3.31
_diffrn_reflns_theta_max         27.44
_reflns_number_total             2402
_reflns_number_gt                1011
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       CrystalClear
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalStructure
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1189P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2402
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1193
_refine_ls_R_factor_gt           0.0754
_refine_ls_wR_factor_ref         0.2201
_refine_ls_wR_factor_gt          0.1910
_refine_ls_goodness_of_fit_ref   0.938
_refine_ls_restrained_S_all      0.938
_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 0.0540(4) 0.1559(6) 0.14602(6) 0.0324(7) Uani 1 1 d . . .
C15 C 0.6251(6) 0.6455(8) 0.13380(7) 0.0247(8) Uani 1 1 d . . .
N2 N 0.2755(4) 0.5200(6) 0.11366(6) 0.0242(8) Uani 1 1 d . . .
N3 N 0.7634(5) 1.5130(7) 0.02642(7) 0.0327(8) Uani 1 1 d . . .
C1 C 0.4502(5) 0.4743(8) 0.13948(8) 0.0216(8) Uani 1 1 d . . .
C2 C 0.3425(6) 0.7154(8) 0.09221(8) 0.0244(9) Uani 1 1 d . . .
C3 C 0.2363(6) 0.8402(9) 0.06117(8) 0.0282(9) Uani 1 1 d . . .
C4 C 0.3408(6) 1.0427(8) 0.04411(8) 0.0267(9) Uani 1 1 d . . .
C5 C 0.5572(6) 1.1231(8) 0.05736(8) 0.0246(9) Uani 1 1 d . . .
C6 C 0.6636(6) 1.0027(8) 0.08685(8) 0.0252(9) Uani 1 1 d . . .
N4 N 0.5553(5) 0.7992(6) 0.10378(6) 0.0232(7) Uani 1 1 d . . .
C8 C 0.6716(6) 1.3386(8) 0.03991(8) 0.0268(9) Uani 1 1 d . . .
C9 C 0.4307(6) 0.2685(8) 0.16770(7) 0.0218(8) Uani 1 1 d . . .
C10 C 0.6087(6) 0.2154(8) 0.19315(8) 0.0264(9) Uani 1 1 d . . .
C11 C 0.5938(6) 0.0216(9) 0.22005(8) 0.0287(9) Uani 1 1 d . . .
C12 C 0.3979(6) -0.1264(9) 0.22172(8) 0.0269(9) Uani 1 1 d . . .
C13 C 0.2192(6) -0.0762(8) 0.19707(8) 0.0277(9) Uani 1 1 d . . .
C14 C 0.2354(6) 0.1188(8) 0.16974(8) 0.0252(9) Uani 1 1 d . . .
H1 H 0.775(5) 0.678(7) 0.1468(8) 0.024(9) Uiso 1 1 d . . .
H2 H 0.820(6) 1.045(8) 0.0979(9) 0.036(10) Uiso 1 1 d . . .
H3 H 0.264(5) 1.140(7) 0.0212(7) 0.011(7) Uiso 1 1 d . . .
H4 H 0.082(6) 0.786(7) 0.0517(8) 0.027(9) Uiso 1 1 d . . .
H5 H 0.746(8) 0.322(9) 0.1910(11) 0.063(14) Uiso 1 1 d . . .
H6 H 0.720(7) -0.008(9) 0.2354(11) 0.061(13) Uiso 1 1 d . . .
H7 H 0.377(6) -0.273(8) 0.2405(9) 0.032(10) Uiso 1 1 d . . .
H8 H 0.076(6) -0.179(7) 0.1976(7) 0.016(8) Uiso 1 1 d . . .
H9 H 0.104(8) 0.313(10) 0.1290(11) 0.063(14) 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 0.0204(14) 0.042(2) 0.0338(12) 0.0045(12) -0.0018(9) -0.0053(14)
C15 0.0275(19) 0.026(2) 0.0202(14) 0.0000(13) -0.0004(12) 0.0008(19)
N2 0.0213(16) 0.029(2) 0.0219(13) 0.0012(12) 0.0028(10) -0.0005(16)
N3 0.0323(19) 0.034(2) 0.0313(15) 0.0023(13) 0.0010(12) -0.0021(18)
C1 0.0203(18) 0.022(2) 0.0225(14) -0.0063(13) 0.0015(11) 0.0036(17)
C2 0.0195(18) 0.030(2) 0.0241(14) -0.0045(14) 0.0063(12) 0.0014(18)
C3 0.0227(19) 0.038(3) 0.0240(15) 0.0001(15) 0.0016(13) 0.0013(19)
C4 0.0249(19) 0.032(3) 0.0228(15) 0.0008(14) 0.0023(12) -0.0028(18)
C5 0.029(2) 0.025(2) 0.0210(14) -0.0017(14) 0.0064(12) -0.0003(18)
C6 0.0233(19) 0.030(2) 0.0228(15) -0.0047(14) 0.0052(12) -0.0029(19)
N4 0.0225(15) 0.026(2) 0.0215(12) -0.0012(11) 0.0020(10) -0.0020(15)
C8 0.028(2) 0.030(2) 0.0227(15) -0.0043(14) 0.0030(13) 0.001(2)
C9 0.0237(18) 0.020(2) 0.0216(14) -0.0030(13) 0.0034(11) -0.0008(17)
C10 0.024(2) 0.028(3) 0.0277(16) -0.0040(14) 0.0016(13) 0.0005(18)
C11 0.031(2) 0.028(2) 0.0264(16) -0.0005(14) 0.0005(13) 0.0002(19)
C12 0.032(2) 0.025(2) 0.0248(15) -0.0002(14) 0.0038(13) 0.0029(19)
C13 0.025(2) 0.030(3) 0.0286(17) -0.0017(14) 0.0072(13) -0.0058(18)
C14 0.0214(18) 0.032(2) 0.0223(15) -0.0065(14) 0.0027(11) 0.0014(18)

_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 C14 1.368(4) . ?
C15 C1 1.380(5) . ?
C15 N4 1.384(4) . ?
N2 C2 1.328(4) . ?
N2 C1 1.391(4) . ?
N3 C8 1.155(4) . ?
C1 C9 1.465(5) . ?
C2 N4 1.390(4) . ?
C2 C3 1.415(5) . ?
C3 C4 1.359(5) . ?
C4 C5 1.421(5) . ?
C5 C6 1.362(5) . ?
C5 C8 1.443(5) . ?
C6 N4 1.372(4) . ?
C9 C14 1.399(5) . ?
C9 C10 1.403(4) . ?
C10 C11 1.385(5) . ?
C11 C12 1.397(5) . ?
C12 C13 1.386(5) . ?
C13 C14 1.402(5) . ?

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 C15 N4 105.2(3) . . ?
C2 N2 C1 106.1(3) . . ?
C15 C1 N2 110.5(3) . . ?
C15 C1 C9 129.2(3) . . ?
N2 C1 C9 120.3(3) . . ?
N2 C2 N4 110.3(3) . . ?
N2 C2 C3 131.2(3) . . ?
N4 C2 C3 118.5(3) . . ?
C4 C3 C2 119.7(3) . . ?
C3 C4 C5 119.5(3) . . ?
C6 C5 C4 121.8(3) . . ?
C6 C5 C8 117.6(3) . . ?
C4 C5 C8 120.7(3) . . ?
C5 C6 N4 118.0(3) . . ?
C6 N4 C15 129.5(3) . . ?
C6 N4 C2 122.6(3) . . ?
C15 N4 C2 107.9(3) . . ?
N3 C8 C5 179.0(3) . . ?
C14 C9 C10 118.5(3) . . ?
C14 C9 C1 120.9(3) . . ?
C10 C9 C1 120.6(3) . . ?
C11 C10 C9 121.5(4) . . ?
C10 C11 C12 119.3(3) . . ?
C13 C12 C11 120.2(4) . . ?
C12 C13 C14 120.3(4) . . ?
O1 C14 C9 122.5(3) . . ?
O1 C14 C13 117.3(3) . . ?
C9 C14 C13 120.1(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
N4 C15 C1 N2 0.0(4) . . . . ?
N4 C15 C1 C9 -179.5(3) . . . . ?
C2 N2 C1 C15 0.4(4) . . . . ?
C2 N2 C1 C9 180.0(3) . . . . ?
C1 N2 C2 N4 -0.7(4) . . . . ?
C1 N2 C2 C3 178.7(4) . . . . ?
N2 C2 C3 C4 178.8(3) . . . . ?
N4 C2 C3 C4 -1.9(5) . . . . ?
C2 C3 C4 C5 1.0(5) . . . . ?
C3 C4 C5 C6 0.0(5) . . . . ?
C3 C4 C5 C8 -179.6(3) . . . . ?
C4 C5 C6 N4 -0.1(5) . . . . ?
C8 C5 C6 N4 179.5(3) . . . . ?
C5 C6 N4 C15 179.9(3) . . . . ?
C5 C6 N4 C2 -0.7(5) . . . . ?
C1 C15 N4 C6 179.0(3) . . . . ?
C1 C15 N4 C2 -0.4(4) . . . . ?
N2 C2 N4 C6 -178.8(3) . . . . ?
C3 C2 N4 C6 1.8(5) . . . . ?
N2 C2 N4 C15 0.7(4) . . . . ?
C3 C2 N4 C15 -178.8(3) . . . . ?
C6 C5 C8 N3 -58(25) . . . . ?
C4 C5 C8 N3 121(24) . . . . ?
C15 C1 C9 C14 178.0(3) . . . . ?
N2 C1 C9 C14 -1.4(5) . . . . ?
C15 C1 C9 C10 -2.5(5) . . . . ?
N2 C1 C9 C10 178.0(3) . . . . ?
C14 C9 C10 C11 -0.5(5) . . . . ?
C1 C9 C10 C11 -180.0(3) . . . . ?
C9 C10 C11 C12 0.6(5) . . . . ?
C10 C11 C12 C13 -1.1(5) . . . . ?
C11 C12 C13 C14 1.5(5) . . . . ?
C10 C9 C14 O1 -179.7(3) . . . . ?
C1 C9 C14 O1 -0.3(5) . . . . ?
C10 C9 C14 C13 0.9(5) . . . . ?
C1 C9 C14 C13 -179.6(3) . . . . ?
C12 C13 C14 O1 179.2(3) . . . . ?
C12 C13 C14 C9 -1.5(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.960
_diffrn_reflns_theta_full        27.44
_diffrn_measured_fraction_theta_full 0.960
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.080
_database_code_depnum_ccdc_archive 'CCDC 965203'
#######################################################################
#
#                 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_2_O

_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H9 N3 O'
_chemical_formula_sum            'C14 H9 N3 O'
_chemical_formula_weight         235.24

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/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                   13.654(6)
_cell_length_b                   7.343(3)
_cell_length_c                   14.200(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 130.054(2)
_cell_angle_gamma                90.00
_cell_volume                     1089.8(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    8291
_cell_measurement_theta_min      3.05
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Platelet
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             488
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9631
_exptl_absorpt_correction_T_max  0.9906
_exptl_absorpt_process_details   ?


_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71070
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_detector       CCD
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       dtprofit.ref
_diffrn_detector_area_resol_mean 14.7059
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8291
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_sigmaI/netI    0.0261
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.21
_diffrn_reflns_theta_max         27.48
_reflns_number_total             2487
_reflns_number_gt                2066
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       CrystalClear
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalStructure
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0605P)²+0.0024P] 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         2487
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0334
_refine_ls_wR_factor_ref         0.0963
_refine_ls_wR_factor_gt          0.0922
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_restrained_S_all      1.097
_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 0.24660(7) 0.48974(10) 0.86922(7) 0.0204(2) Uani 1 1 d . . .
N1 N 0.20109(8) 0.40738(11) 0.66434(8) 0.0157(2) Uani 1 1 d . . .
N2 N 0.08939(8) 0.29812(11) 0.47336(8) 0.0147(2) Uani 1 1 d . . .
N3 N 0.11054(10) 0.21413(15) 0.15480(10) 0.0302(3) Uani 1 1 d . . .
C1 C 0.05747(10) 0.31849(13) 0.70769(9) 0.0147(2) Uani 1 1 d . . .
C2 C 0.13572(10) 0.40195(14) 0.82431(9) 0.0163(2) Uani 1 1 d . . .
C3 C 0.10189(11) 0.39716(15) 0.89846(10) 0.0196(2) Uani 1 1 d . . .
C4 C -0.00887(11) 0.30982(15) 0.85796(10) 0.0216(3) Uani 1 1 d . . .
C5 C -0.08761(11) 0.22597(15) 0.74284(10) 0.0208(3) Uani 1 1 d . . .
C6 C -0.05438(10) 0.23087(15) 0.66899(10) 0.0178(2) Uani 1 1 d . . .
C7 C 0.08957(10) 0.32489(13) 0.62703(9) 0.0147(2) Uani 1 1 d . . .
C8 C 0.01957(10) 0.25795(14) 0.50973(10) 0.0152(2) Uani 1 1 d . . .
C9 C 0.20009(9) 0.38958(13) 0.57049(9) 0.0148(2) Uani 1 1 d . . .
C10 C 0.28908(10) 0.44314(15) 0.55625(10) 0.0171(2) Uani 1 1 d . . .
C11 C 0.26711(10) 0.40204(14) 0.45045(10) 0.0186(2) Uani 1 1 d . . .
C12 C 0.15370(10) 0.30532(14) 0.35465(10) 0.0178(2) Uani 1 1 d . . .
C13 C 0.06591(10) 0.25612(14) 0.36676(10) 0.0167(2) Uani 1 1 d . . .
C14 C 0.12910(11) 0.25655(15) 0.24281(10) 0.0213(3) Uani 1 1 d . . .
H1 H -0.0616(13) 0.1970(18) 0.4547(12) 0.026(3) Uiso 1 1 d . . .
H2 H -0.0156(12) 0.1912(17) 0.3043(12) 0.021(3) Uiso 1 1 d . . .
H3 H 0.3642(12) 0.5106(16) 0.6210(11) 0.018(3) Uiso 1 1 d . . .
H4 H 0.1591(11) 0.4613(18) 0.9791(12) 0.021(3) Uiso 1 1 d . . .
H5 H -0.0333(12) 0.3072(18) 0.9095(12) 0.027(3) Uiso 1 1 d . . .
H6 H -0.1125(13) 0.1712(17) 0.5864(13) 0.024(3) Uiso 1 1 d . . .
H7 H -0.1691(13) 0.1645(18) 0.7113(12) 0.029(3) Uiso 1 1 d . . .
H8 H 0.3289(11) 0.4378(17) 0.4399(11) 0.019(3) Uiso 1 1 d . . .
H9 H 0.2543(14) 0.485(2) 0.8053(15) 0.048(4) 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 0.0204(4) 0.0216(4) 0.0170(4) -0.0038(3) 0.0110(3) -0.0051(3)
N1 0.0157(5) 0.0153(4) 0.0151(4) 0.0010(3) 0.0095(4) 0.0000(3)
N2 0.0142(4) 0.0146(4) 0.0139(4) 0.0010(3) 0.0084(4) 0.0008(3)
N3 0.0302(6) 0.0406(6) 0.0254(5) -0.0032(5) 0.0204(5) -0.0009(5)
C1 0.0147(5) 0.0140(5) 0.0139(5) 0.0022(4) 0.0085(4) 0.0029(4)
C2 0.0157(5) 0.0140(5) 0.0160(5) 0.0021(4) 0.0087(4) 0.0025(4)
C3 0.0220(6) 0.0207(5) 0.0155(5) 0.0019(4) 0.0118(5) 0.0048(4)
C4 0.0248(6) 0.0245(6) 0.0207(6) 0.0052(5) 0.0170(5) 0.0068(5)
C5 0.0179(6) 0.0240(6) 0.0224(6) 0.0044(4) 0.0139(5) 0.0027(4)
C6 0.0162(6) 0.0186(5) 0.0168(5) 0.0019(4) 0.0098(5) 0.0015(4)
C7 0.0142(5) 0.0125(5) 0.0160(5) 0.0025(4) 0.0090(4) 0.0023(4)
C8 0.0134(5) 0.0163(5) 0.0155(5) 0.0002(4) 0.0091(5) 0.0002(4)
C9 0.0145(5) 0.0129(5) 0.0134(5) 0.0015(4) 0.0073(4) 0.0015(4)
C10 0.0151(5) 0.0168(5) 0.0171(5) 0.0020(4) 0.0094(5) 0.0000(4)
C11 0.0185(6) 0.0190(5) 0.0212(6) 0.0037(4) 0.0141(5) 0.0020(4)
C12 0.0200(6) 0.0180(5) 0.0166(5) 0.0031(4) 0.0124(5) 0.0041(4)
C13 0.0168(6) 0.0170(5) 0.0147(5) 0.0003(4) 0.0094(5) 0.0015(4)
C14 0.0198(6) 0.0243(6) 0.0222(6) 0.0009(4) 0.0147(5) 0.0008(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
O1 C2 1.3682(14) . ?
N1 C9 1.3304(14) . ?
N1 C7 1.3885(15) . ?
N2 C13 1.3656(15) . ?
N2 C8 1.3770(14) . ?
N2 C9 1.3982(14) . ?
N3 C14 1.1468(16) . ?
C1 C6 1.4030(16) . ?
C1 C2 1.4080(16) . ?
C1 C7 1.4670(15) . ?
C2 C3 1.3961(15) . ?
C3 C4 1.3820(18) . ?
C4 C5 1.3948(17) . ?
C5 C6 1.3853(16) . ?
C7 C8 1.3713(16) . ?
C9 C10 1.4100(16) . ?
C10 C11 1.3631(16) . ?
C11 C12 1.4289(16) . ?
C12 C13 1.3646(16) . ?
C12 C14 1.4411(16) . ?

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
C9 N1 C7 105.85(8) . . ?
C13 N2 C8 129.94(9) . . ?
C13 N2 C9 122.38(9) . . ?
C8 N2 C9 107.63(9) . . ?
C6 C1 C2 118.11(9) . . ?
C6 C1 C7 120.38(10) . . ?
C2 C1 C7 121.50(10) . . ?
O1 C2 C3 117.66(10) . . ?
O1 C2 C1 121.86(9) . . ?
C3 C2 C1 120.48(11) . . ?
C4 C3 C2 120.16(11) . . ?
C3 C4 C5 120.29(10) . . ?
C6 C5 C4 119.66(11) . . ?
C5 C6 C1 121.31(11) . . ?
C8 C7 N1 110.85(9) . . ?
C8 C7 C1 127.72(10) . . ?
N1 C7 C1 121.42(9) . . ?
C7 C8 N2 105.61(10) . . ?
N1 C9 N2 110.06(9) . . ?
N1 C9 C10 131.45(10) . . ?
N2 C9 C10 118.48(10) . . ?
C11 C10 C9 119.84(10) . . ?
C10 C11 C12 119.63(10) . . ?
C13 C12 C11 120.89(10) . . ?
C13 C12 C14 118.19(10) . . ?
C11 C12 C14 120.93(10) . . ?
C12 C13 N2 118.77(10) . . ?
N3 C14 C12 178.55(13) . . ?

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 O1 179.79(9) . . . . ?
C7 C1 C2 O1 -1.35(15) . . . . ?
C6 C1 C2 C3 -0.13(15) . . . . ?
C7 C1 C2 C3 178.73(9) . . . . ?
O1 C2 C3 C4 -179.78(9) . . . . ?
C1 C2 C3 C4 0.14(16) . . . . ?
C2 C3 C4 C5 -0.01(16) . . . . ?
C3 C4 C5 C6 -0.12(16) . . . . ?
C4 C5 C6 C1 0.13(16) . . . . ?
C2 C1 C6 C5 0.00(15) . . . . ?
C7 C1 C6 C5 -178.88(9) . . . . ?
C9 N1 C7 C8 -0.57(11) . . . . ?
C9 N1 C7 C1 -179.80(9) . . . . ?
C6 C1 C7 C8 2.30(16) . . . . ?
C2 C1 C7 C8 -176.53(10) . . . . ?
C6 C1 C7 N1 -178.60(9) . . . . ?
C2 C1 C7 N1 2.57(15) . . . . ?
N1 C7 C8 N2 0.51(11) . . . . ?
C1 C7 C8 N2 179.69(9) . . . . ?
C13 N2 C8 C7 177.22(10) . . . . ?
C9 N2 C8 C7 -0.26(11) . . . . ?
C7 N1 C9 N2 0.39(11) . . . . ?
C7 N1 C9 C10 -178.53(11) . . . . ?
C13 N2 C9 N1 -177.80(9) . . . . ?
C8 N2 C9 N1 -0.08(11) . . . . ?
C13 N2 C9 C10 1.28(14) . . . . ?
C8 N2 C9 C10 178.99(9) . . . . ?
N1 C9 C10 C11 177.52(10) . . . . ?
N2 C9 C10 C11 -1.32(15) . . . . ?
C9 C10 C11 C12 0.18(16) . . . . ?
C10 C11 C12 C13 1.10(16) . . . . ?
C10 C11 C12 C14 -178.69(10) . . . . ?
C11 C12 C13 N2 -1.17(15) . . . . ?
C14 C12 C13 N2 178.63(9) . . . . ?
C8 N2 C13 C12 -177.19(10) . . . . ?
C9 N2 C13 C12 -0.03(15) . . . . ?
C13 C12 C14 N3 -82(5) . . . . ?
C11 C12 C14 N3 98(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.041
_database_code_depnum_ccdc_archive 'CCDC 965204'
#######################################################################
#
#                 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_2_R

_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H9 N3 O'
_chemical_formula_sum            'C14 H9 N3 O'
_chemical_formula_weight         235.24

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/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                   3.8196(10)
_cell_length_b                   11.356(3)
_cell_length_c                   25.246(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.1960(10)
_cell_angle_gamma                90.00
_cell_volume                     1093.3(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    8368
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             488
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9632
_exptl_absorpt_correction_T_max  0.9860
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71070
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_detector       CCD
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       dtprofit.ref
_diffrn_detector_area_resol_mean 14.7059
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8368
_diffrn_reflns_av_R_equivalents  0.1100
_diffrn_reflns_av_sigmaI/netI    0.1177
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         3.02
_diffrn_reflns_theta_max         27.48
_reflns_number_total             2479
_reflns_number_gt                1750
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       CrystalClear
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalStructure
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0512P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2479
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0706
_refine_ls_R_factor_gt           0.0591
_refine_ls_wR_factor_ref         0.1328
_refine_ls_wR_factor_gt          0.1298
_refine_ls_goodness_of_fit_ref   0.929
_refine_ls_restrained_S_all      0.929
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.8386(3) 0.67462(11) 0.18329(5) 0.0193(3) Uani 1 1 d . . .
C15 C 0.3369(4) 0.39160(15) 0.26091(7) 0.0133(4) Uani 1 1 d . . .
N2 N 0.5872(4) 0.57286(12) 0.26631(6) 0.0136(4) Uani 1 1 d . . .
N3 N 0.0138(4) 0.33779(15) 0.48696(7) 0.0265(4) Uani 1 1 d . . .
C1 C 0.4941(4) 0.47939(14) 0.23296(7) 0.0120(4) Uani 1 1 d . . .
N4 N 0.3317(4) 0.43148(12) 0.31237(5) 0.0117(3) Uani 1 1 d . . .
C3 C 0.2113(4) 0.37844(15) 0.35660(7) 0.0133(4) Uani 1 1 d . . .
C4 C 0.2426(4) 0.43790(16) 0.40354(7) 0.0144(4) Uani 1 1 d . . .
C5 C 0.3973(4) 0.55213(16) 0.40721(7) 0.0153(4) Uani 1 1 d . . .
C6 C 0.5155(5) 0.60371(16) 0.36301(7) 0.0149(4) Uani 1 1 d . . .
C7 C 0.4872(4) 0.54343(15) 0.31408(7) 0.0123(4) Uani 1 1 d . . .
C8 C 0.1149(5) 0.38181(15) 0.45001(7) 0.0175(4) Uani 1 1 d . . .
C9 C 0.5710(4) 0.48087(15) 0.17693(7) 0.0134(4) Uani 1 1 d . . .
C10 C 0.7360(4) 0.57843(15) 0.15411(7) 0.0143(4) Uani 1 1 d . . .
C11 C 0.7991(5) 0.57862(17) 0.10035(7) 0.0185(4) Uani 1 1 d . . .
C12 C 0.7055(5) 0.48320(17) 0.06898(8) 0.0199(4) Uani 1 1 d . . .
C13 C 0.5453(5) 0.38488(17) 0.09059(7) 0.0196(5) Uani 1 1 d . . .
C14 C 0.4790(5) 0.38579(16) 0.14393(7) 0.0165(4) Uani 1 1 d . . .
H1 H 0.231(4) 0.3159(15) 0.2504(6) 0.006(4) Uiso 1 1 d . . .
H2 H 0.096(4) 0.3019(16) 0.3505(7) 0.012(5) Uiso 1 1 d . . .
H3 H 0.415(5) 0.5906(17) 0.4411(7) 0.024(5) Uiso 1 1 d . . .
H4 H 0.627(5) 0.6770(18) 0.3632(7) 0.023(5) Uiso 1 1 d . . .
H5 H 0.912(5) 0.6484(18) 0.0850(7) 0.029(6) Uiso 1 1 d . . .
H6 H 0.757(5) 0.4857(16) 0.0311(8) 0.022(5) Uiso 1 1 d . . .
H7 H 0.478(5) 0.3180(17) 0.0675(7) 0.024(5) Uiso 1 1 d . . .
H8 H 0.365(4) 0.3154(17) 0.1608(7) 0.017(5) Uiso 1 1 d . . .
H9 H 0.790(6) 0.6595(19) 0.2190(9) 0.039(7) 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 0.0262(7) 0.0104(7) 0.0217(7) 0.0015(5) 0.0058(6) -0.0036(6)
C15 0.0155(9) 0.0077(9) 0.0168(9) -0.0022(7) 0.0023(7) 0.0016(7)
N2 0.0145(8) 0.0084(8) 0.0182(8) 0.0006(6) 0.0026(6) 0.0003(6)
N3 0.0344(10) 0.0224(10) 0.0234(9) 0.0017(8) 0.0076(8) -0.0021(8)
C1 0.0099(8) 0.0073(9) 0.0189(9) -0.0001(7) 0.0002(7) 0.0034(7)
N4 0.0118(7) 0.0063(7) 0.0171(8) -0.0004(6) 0.0032(6) 0.0013(6)
C3 0.0134(9) 0.0074(9) 0.0197(9) 0.0016(7) 0.0056(8) 0.0005(7)
C4 0.0119(9) 0.0120(9) 0.0196(9) 0.0021(7) 0.0043(7) 0.0033(7)
C5 0.0157(9) 0.0119(9) 0.0184(9) -0.0034(8) 0.0017(8) 0.0028(7)
C6 0.0146(9) 0.0077(9) 0.0225(10) -0.0021(7) 0.0015(8) 0.0005(7)
C7 0.0100(8) 0.0059(9) 0.0213(9) 0.0003(7) 0.0016(7) 0.0007(7)
C8 0.0193(10) 0.0132(10) 0.0203(10) -0.0022(8) 0.0027(8) 0.0024(8)
C9 0.0116(9) 0.0083(9) 0.0206(9) 0.0013(7) 0.0020(7) 0.0049(7)
C10 0.0125(9) 0.0089(9) 0.0216(9) 0.0009(7) 0.0016(7) 0.0040(7)
C11 0.0160(9) 0.0183(11) 0.0216(10) 0.0075(8) 0.0038(8) 0.0030(8)
C12 0.0164(10) 0.0261(11) 0.0174(9) 0.0021(8) 0.0036(8) 0.0071(8)
C13 0.0187(10) 0.0187(11) 0.0214(10) -0.0042(8) 0.0006(8) 0.0047(8)
C14 0.0155(9) 0.0113(10) 0.0227(10) 0.0008(8) 0.0031(8) 0.0020(7)

_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 C10 1.363(2) . ?
C15 N4 1.377(2) . ?
C15 C1 1.378(2) . ?
N2 C7 1.328(2) . ?
N2 C1 1.389(2) . ?
N3 C8 1.144(2) . ?
C1 C9 1.461(2) . ?
N4 C3 1.371(2) . ?
N4 C7 1.403(2) . ?
C3 C4 1.363(2) . ?
C4 C5 1.426(3) . ?
C4 C8 1.444(2) . ?
C5 C6 1.359(2) . ?
C6 C7 1.411(2) . ?
C9 C14 1.397(2) . ?
C9 C10 1.413(2) . ?
C10 C11 1.392(2) . ?
C11 C12 1.377(3) . ?
C12 C13 1.399(3) . ?
C13 C14 1.384(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
N4 C15 C1 105.96(15) . . ?
C7 N2 C1 106.34(14) . . ?
C15 C1 N2 110.27(15) . . ?
C15 C1 C9 128.39(16) . . ?
N2 C1 C9 121.32(15) . . ?
C3 N4 C15 130.35(15) . . ?
C3 N4 C7 122.27(14) . . ?
C15 N4 C7 107.37(14) . . ?
C4 C3 N4 118.25(17) . . ?
C3 C4 C5 121.52(16) . . ?
C3 C4 C8 118.07(17) . . ?
C5 C4 C8 120.40(16) . . ?
C6 C5 C4 119.60(17) . . ?
C5 C6 C7 119.79(18) . . ?
N2 C7 N4 110.06(15) . . ?
N2 C7 C6 131.38(17) . . ?
N4 C7 C6 118.56(16) . . ?
N3 C8 C4 179.7(2) . . ?
C14 C9 C10 117.78(17) . . ?
C14 C9 C1 120.74(16) . . ?
C10 C9 C1 121.47(15) . . ?
O1 C10 C11 117.75(16) . . ?
O1 C10 C9 121.97(16) . . ?
C11 C10 C9 120.28(17) . . ?
C12 C11 C10 120.39(17) . . ?
C11 C12 C13 120.60(18) . . ?
C14 C13 C12 118.77(18) . . ?
C13 C14 C9 122.18(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
N4 C15 C1 N2 0.18(19) . . . . ?
N4 C15 C1 C9 178.67(15) . . . . ?
C7 N2 C1 C15 -0.33(18) . . . . ?
C7 N2 C1 C9 -178.95(14) . . . . ?
C1 C15 N4 C3 -178.65(15) . . . . ?
C1 C15 N4 C7 0.04(18) . . . . ?
C15 N4 C3 C4 179.11(16) . . . . ?
C7 N4 C3 C4 0.6(2) . . . . ?
N4 C3 C4 C5 -0.3(3) . . . . ?
N4 C3 C4 C8 179.88(14) . . . . ?
C3 C4 C5 C6 0.3(3) . . . . ?
C8 C4 C5 C6 -179.87(16) . . . . ?
C4 C5 C6 C7 -0.6(3) . . . . ?
C1 N2 C7 N4 0.36(18) . . . . ?
C1 N2 C7 C6 179.72(18) . . . . ?
C3 N4 C7 N2 178.56(14) . . . . ?
C15 N4 C7 N2 -0.25(18) . . . . ?
C3 N4 C7 C6 -0.9(2) . . . . ?
C15 N4 C7 C6 -179.71(15) . . . . ?
C5 C6 C7 N2 -178.44(17) . . . . ?
C5 C6 C7 N4 0.9(2) . . . . ?
C3 C4 C8 N3 -169(100) . . . . ?
C5 C4 C8 N3 11(51) . . . . ?
C15 C1 C9 C14 1.0(3) . . . . ?
N2 C1 C9 C14 179.38(15) . . . . ?
C15 C1 C9 C10 -179.79(17) . . . . ?
N2 C1 C9 C10 -1.4(2) . . . . ?
C14 C9 C10 O1 -179.29(15) . . . . ?
C1 C9 C10 O1 1.5(2) . . . . ?
C14 C9 C10 C11 0.6(2) . . . . ?
C1 C9 C10 C11 -178.56(15) . . . . ?
O1 C10 C11 C12 179.13(16) . . . . ?
C9 C10 C11 C12 -0.8(3) . . . . ?
C10 C11 C12 C13 0.1(3) . . . . ?
C11 C12 C13 C14 0.7(3) . . . . ?
C12 C13 C14 C9 -0.9(3) . . . . ?
C10 C9 C14 C13 0.2(3) . . . . ?
C1 C9 C14 C13 179.41(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.364
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.070
_database_code_depnum_ccdc_archive 'CCDC 965205'
