# 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_LN_AM_MF_amb

_audit_creation_date             2012-03-06T15:17:29-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
'1,5-dimethyl-3-(p-ethynylphenyl)-6-oxoverdazyl '
_chemical_formula_moiety         'C12 H11 N4 O'
_chemical_formula_sum            'C12 H11 N4 O'
_chemical_formula_weight         227.25
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.0513(9)
_cell_length_b                   11.154(2)
_cell_length_c                   12.902(3)
_cell_angle_alpha                104.617(11)
_cell_angle_beta                 94.207(11)
_cell_angle_gamma                94.195(12)
_cell_volume                     560.1(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    455
_cell_measurement_theta_min      3.28
_cell_measurement_theta_max      23.12
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.05
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             238
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.891
_exptl_absorpt_correction_T_max  0.995


#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_detector                 'CCD plate'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_unetI/netI     0.0468
_diffrn_reflns_number            6796
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.72
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.962
_reflns_number_total             2469
_reflns_number_gt                1498
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2 (Bruker, 2006)'
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2006)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2006)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  
;
           WinGX publication routines (Farrugia, 1999),
           CRYSCAL (T. Roisnel, local program)
;

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0831P)²+0.0431P] 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_number_reflns         2469
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0959
_refine_ls_R_factor_gt           0.0537
_refine_ls_wR_factor_ref         0.1663
_refine_ls_wR_factor_gt          0.1406
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_restrained_S_all      0.993
_refine_ls_shift/su_max          0.02
_refine_ls_shift/su_mean         0.004
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.034


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.2367(4) 0.29647(13) 0.44553(10) 0.0648(4) Uani 1 1 d . . .
C2 C 0.3457(4) 0.28766(17) 0.35859(14) 0.0467(5) Uani 1 1 d . . .
N3 N 0.4907(4) 0.18538(13) 0.30580(11) 0.0479(4) Uani 1 1 d . . .
C4 C 0.5342(5) 0.08417(19) 0.35649(16) 0.0627(6) Uani 1 1 d . . .
H4A H 0.638 0.0198 0.3095 0.094 Uiso 0.5 1 calc PR . .
H4B H 0.3212 0.051 0.3703 0.094 Uiso 0.5 1 calc PR . .
H4C H 0.6721 0.1149 0.4231 0.094 Uiso 0.5 1 calc PR . .
H4D H 0.4495 0.104 0.4258 0.094 Uiso 0.5 1 calc PR . .
H4E H 0.7663 0.0728 0.365 0.094 Uiso 0.5 1 calc PR . .
H4F H 0.4155 0.0089 0.3121 0.094 Uiso 0.5 1 calc PR . .
N5 N 0.6115(4) 0.17135(14) 0.20761(11) 0.0475(4) Uani 1 1 d . . .
C6 C 0.5749(4) 0.26589(15) 0.16373(13) 0.0408(4) Uani 1 1 d . . .
N7 N 0.4429(4) 0.37098(14) 0.20664(11) 0.0489(4) Uani 1 1 d . . .
N8 N 0.3349(4) 0.37979(14) 0.30579(11) 0.0488(4) Uani 1 1 d . . .
C9 C 0.2040(5) 0.49703(18) 0.35461(16) 0.0631(6) Uani 1 1 d . . .
H9A H 0.2146 0.5502 0.3067 0.095 Uiso 0.5 1 calc PR . .
H9B H 0.334 0.537 0.4213 0.095 Uiso 0.5 1 calc PR . .
H9C H -0.0229 0.4811 0.368 0.095 Uiso 0.5 1 calc PR . .
H9D H 0.1359 0.4953 0.424 0.095 Uiso 0.5 1 calc PR . .
H9E H 0.0164 0.5086 0.3094 0.095 Uiso 0.5 1 calc PR . .
H9F H 0.3734 0.5644 0.3626 0.095 Uiso 0.5 1 calc PR . .
C10 C 0.6911(4) 0.25389(16) 0.05571(13) 0.0410(4) Uani 1 1 d . . .
C11 C 0.7964(5) 0.14322(16) -0.00188(14) 0.0482(5) Uani 1 1 d . . .
H11 H 0.7968 0.0756 0.0281 0.058 Uiso 1 1 calc R . .
C12 C 0.9006(5) 0.13185(17) -0.10295(14) 0.0504(5) Uani 1 1 d . . .
H12 H 0.9698 0.0567 -0.1405 0.061 Uiso 1 1 calc R . .
C13 C 0.9029(4) 0.23170(16) -0.14904(13) 0.0438(5) Uani 1 1 d . . .
C14 C 0.7960(5) 0.34238(17) -0.09093(15) 0.0570(5) Uani 1 1 d . . .
H14 H 0.793 0.4099 -0.1209 0.068 Uiso 1 1 calc R . .
C15 C 0.6947(5) 0.35355(17) 0.00997(15) 0.0531(5) Uani 1 1 d . . .
H15 H 0.6277 0.4289 0.048 0.064 Uiso 1 1 calc R . .
C16 C 1.0108(5) 0.22222(17) -0.25430(15) 0.0509(5) Uani 1 1 d . . .
C17 C 1.0994(5) 0.21805(19) -0.33936(17) 0.0632(6) Uani 1 1 d . . .
H17 H 1.1698 0.2147 -0.4069 0.076 Uiso 1 1 calc R . .





#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 1.2190(19) . ?
C2 N3 1.369(2) . ?
C2 N8 1.370(2) . ?
N3 N5 1.3680(19) . ?
N3 C4 1.455(2) . ?
C4 H4A 0.96 . ?
C4 H4B 0.96 . ?
C4 H4C 0.96 . ?
C4 H4D 0.96 . ?
C4 H4E 0.96 . ?
C4 H4F 0.96 . ?
N5 C6 1.329(2) . ?
C6 N7 1.332(2) . ?
C6 C10 1.481(2) . ?
N7 N8 1.3647(19) . ?
N8 C9 1.457(2) . ?
C9 H9A 0.96 . ?
C9 H9B 0.96 . ?
C9 H9C 0.96 . ?
C9 H9D 0.96 . ?
C9 H9E 0.96 . ?
C9 H9F 0.96 . ?
C10 C15 1.384(2) . ?
C10 C11 1.385(2) . ?
C11 C12 1.378(2) . ?
C11 H11 0.93 . ?
C12 C13 1.388(2) . ?
C12 H12 0.93 . ?
C13 C14 1.390(2) . ?
C13 C16 1.438(2) . ?
C14 C15 1.372(2) . ?
C14 H14 0.93 . ?
C15 H15 0.93 . ?
C16 C17 1.170(2) . ?
C17 H17 0.93 . ?


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 C2 N3 122.92(17) . . ?
O1 C2 N8 122.72(17) . . ?
N3 C2 N8 114.37(16) . . ?
N5 N3 C2 124.62(15) . . ?
N5 N3 C4 115.76(15) . . ?
C2 N3 C4 119.59(16) . . ?
N3 C4 H4A 109.5 . . ?
N3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N3 C4 H4D 109.5 . . ?
H4A C4 H4D 141.1 . . ?
H4B C4 H4D 56.3 . . ?
H4C C4 H4D 56.3 . . ?
N3 C4 H4E 109.5 . . ?
H4A C4 H4E 56.3 . . ?
H4B C4 H4E 141.1 . . ?
H4C C4 H4E 56.3 . . ?
H4D C4 H4E 109.5 . . ?
N3 C4 H4F 109.5 . . ?
H4A C4 H4F 56.3 . . ?
H4B C4 H4F 56.3 . . ?
H4C C4 H4F 141.1 . . ?
H4D C4 H4F 109.5 . . ?
H4E C4 H4F 109.5 . . ?
C6 N5 N3 114.76(14) . . ?
N5 C6 N7 126.78(16) . . ?
N5 C6 C10 117.10(16) . . ?
N7 C6 C10 116.12(16) . . ?
C6 N7 N8 115.21(15) . . ?
N7 N8 C2 124.19(15) . . ?
N7 N8 C9 115.12(15) . . ?
C2 N8 C9 120.69(16) . . ?
N8 C9 H9A 109.5 . . ?
N8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N8 C9 H9D 109.5 . . ?
H9A C9 H9D 141.1 . . ?
H9B C9 H9D 56.3 . . ?
H9C C9 H9D 56.3 . . ?
N8 C9 H9E 109.5 . . ?
H9A C9 H9E 56.3 . . ?
H9B C9 H9E 141.1 . . ?
H9C C9 H9E 56.3 . . ?
H9D C9 H9E 109.5 . . ?
N8 C9 H9F 109.5 . . ?
H9A C9 H9F 56.3 . . ?
H9B C9 H9F 56.3 . . ?
H9C C9 H9F 141.1 . . ?
H9D C9 H9F 109.5 . . ?
H9E C9 H9F 109.5 . . ?
C15 C10 C11 118.59(17) . . ?
C15 C10 C6 120.35(17) . . ?
C11 C10 C6 121.06(16) . . ?
C12 C11 C10 120.93(17) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C11 C12 C13 120.48(17) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C14 C13 C12 118.28(16) . . ?
C14 C13 C16 120.18(16) . . ?
C12 C13 C16 121.54(16) . . ?
C15 C14 C13 121.03(17) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C14 C15 C10 120.67(18) . . ?
C14 C15 H15 119.7 . . ?
C10 C15 H15 119.7 . . ?
C17 C16 C13 178.1(2) . . ?
C16 C17 H17 180 . . ?


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 C2 N3 N5 179.06(15) . . . . ?
N8 C2 N3 N5 -1.3(2) . . . . ?
O1 C2 N3 C4 -3.1(3) . . . . ?
N8 C2 N3 C4 176.51(15) . . . . ?
C2 N3 N5 C6 -0.9(2) . . . . ?
C4 N3 N5 C6 -178.76(15) . . . . ?
N3 N5 C6 N7 1.7(3) . . . . ?
N3 N5 C6 C10 -178.00(13) . . . . ?
N5 C6 N7 N8 -0.3(3) . . . . ?
C10 C6 N7 N8 179.49(13) . . . . ?
C6 N7 N8 C2 -2.3(2) . . . . ?
C6 N7 N8 C9 177.41(16) . . . . ?
O1 C2 N8 N7 -177.38(15) . . . . ?
N3 C2 N8 N7 3.0(2) . . . . ?
O1 C2 N8 C9 2.9(3) . . . . ?
N3 C2 N8 C9 -176.72(16) . . . . ?
N5 C6 C10 C15 -172.96(15) . . . . ?
N7 C6 C10 C15 7.3(3) . . . . ?
N5 C6 C10 C11 7.4(3) . . . . ?
N7 C6 C10 C11 -172.37(15) . . . . ?
C15 C10 C11 C12 -0.4(3) . . . . ?
C6 C10 C11 C12 179.20(15) . . . . ?
C10 C11 C12 C13 0.2(3) . . . . ?
C11 C12 C13 C14 -0.4(3) . . . . ?
C11 C12 C13 C16 179.94(16) . . . . ?
C12 C13 C14 C15 0.8(3) . . . . ?
C16 C13 C14 C15 -179.47(17) . . . . ?
C13 C14 C15 C10 -1.1(3) . . . . ?
C11 C10 C15 C14 0.9(3) . . . . ?
C6 C10 C15 C14 -178.74(16) . . . . ?
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane'
_exptl_crystal_preparation       'Magnetic properties'
_database_code_depnum_ccdc_archive 'CCDC 1012865'
#######################################################################
#
#                 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_LN_AM_MF_200K

_audit_creation_date             2012-03-06T18:13:38-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C12 H11 N4 O'
_chemical_formula_sum            'C12 H11 N4 O'
_chemical_formula_weight         227.25
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   3.9940(4)
_cell_length_b                   11.1412(9)
_cell_length_c                   12.8857(11)
_cell_angle_alpha                104.875(4)
_cell_angle_beta                 94.557(4)
_cell_angle_gamma                93.967(4)
_cell_volume                     550.03(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    1617
_cell_measurement_theta_min      2.82
_cell_measurement_theta_max      27.38
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.05
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             238
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.887
_exptl_absorpt_correction_T_max  0.995


#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_detector                 'CCD plate'
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_unetI/netI     0.046
_diffrn_reflns_number            6715
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         4.21
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_reflns_number_total             2472
_reflns_number_gt                1673
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2 (Bruker, 2006)'
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2006)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2006)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  
;
           WinGX publication routines (Farrugia, 1999),
           CRYSCAL (T. Roisnel, local program)
;

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0576P)²+0.1753P] 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_number_reflns         2472
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0763
_refine_ls_R_factor_gt           0.0502
_refine_ls_wR_factor_ref         0.134
_refine_ls_wR_factor_gt          0.1192
_refine_ls_goodness_of_fit_ref   0.957
_refine_ls_restrained_S_all      0.957
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.041


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.2267(3) 0.29840(11) 0.44555(9) 0.0429(3) Uani 1 1 d . . .
C2 C 0.3386(4) 0.28962(15) 0.35859(12) 0.0317(4) Uani 1 1 d . . .
N3 N 0.4835(3) 0.18604(12) 0.30536(10) 0.0320(3) Uani 1 1 d . . .
C4 C 0.5257(5) 0.08485(16) 0.35692(14) 0.0410(4) Uani 1 1 d . . .
H4A H 0.6678 0.1167 0.4255 0.062 Uiso 1 1 calc R . .
H4B H 0.6333 0.0184 0.3094 0.062 Uiso 1 1 calc R . .
H4C H 0.3045 0.0516 0.3704 0.062 Uiso 1 1 calc R . .
N5 N 0.6078(3) 0.17146(12) 0.20746(10) 0.0320(3) Uani 1 1 d . . .
C6 C 0.5712(4) 0.26635(14) 0.16340(11) 0.0275(3) Uani 1 1 d . . .
N7 N 0.4401(3) 0.37270(12) 0.20642(10) 0.0332(3) Uani 1 1 d . . .
N8 N 0.3302(3) 0.38178(13) 0.30605(10) 0.0330(3) Uani 1 1 d . . .
C9 C 0.1996(5) 0.50002(16) 0.35504(14) 0.0420(4) Uani 1 1 d . . .
H9A H 0.2137 0.5545 0.3064 0.063 Uiso 0.5 1 calc PR . .
H9B H 0.3336 0.5403 0.4238 0.063 Uiso 0.5 1 calc PR . .
H9C H -0.0362 0.4847 0.3678 0.063 Uiso 0.5 1 calc PR . .
H9D H 0.127 0.4985 0.4256 0.063 Uiso 0.5 1 calc PR . .
H9E H 0.0071 0.5127 0.3082 0.063 Uiso 0.5 1 calc PR . .
H9F H 0.377 0.5683 0.3642 0.063 Uiso 0.5 1 calc PR . .
C10 C 0.6893(4) 0.25370(14) 0.05523(11) 0.0269(3) Uani 1 1 d . . .
C11 C 0.7920(4) 0.14129(15) -0.00314(12) 0.0314(4) Uani 1 1 d . . .
H11 H 0.7892 0.0719 0.027 0.038 Uiso 1 1 calc R . .
C12 C 0.8980(4) 0.12955(15) -0.10449(12) 0.0323(4) Uani 1 1 d . . .
H12 H 0.9681 0.0523 -0.1433 0.039 Uiso 1 1 calc R . .
C13 C 0.9029(4) 0.23009(14) -0.15023(12) 0.0296(4) Uani 1 1 d . . .
C14 C 0.7980(4) 0.34250(15) -0.09172(13) 0.0375(4) Uani 1 1 d . . .
H14 H 0.7979 0.4117 -0.1221 0.045 Uiso 1 1 calc R . .
C15 C 0.6949(4) 0.35395(15) 0.00951(13) 0.0350(4) Uani 1 1 d . . .
H15 H 0.6267 0.4313 0.0486 0.042 Uiso 1 1 calc R . .
C16 C 1.0128(4) 0.22009(15) -0.25592(13) 0.0338(4) Uani 1 1 d . . .
C17 C 1.1026(5) 0.21566(17) -0.34163(14) 0.0416(4) Uani 1 1 d . . .
H17 H 1.175 0.2121 -0.4107 0.05 Uiso 1 1 calc R . .





#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 1.2225(18) . ?
C2 N8 1.368(2) . ?
C2 N3 1.373(2) . ?
N3 N5 1.3674(17) . ?
N3 C4 1.461(2) . ?
C4 H4A 0.98 . ?
C4 H4B 0.98 . ?
C4 H4C 0.98 . ?
N5 C6 1.333(2) . ?
C6 N7 1.334(2) . ?
C6 C10 1.482(2) . ?
N7 N8 1.3711(17) . ?
N8 C9 1.458(2) . ?
C9 H9A 0.98 . ?
C9 H9B 0.98 . ?
C9 H9C 0.98 . ?
C9 H9D 0.98 . ?
C9 H9E 0.98 . ?
C9 H9F 0.98 . ?
C10 C15 1.390(2) . ?
C10 C11 1.393(2) . ?
C11 C12 1.382(2) . ?
C11 H11 0.95 . ?
C12 C13 1.393(2) . ?
C12 H12 0.95 . ?
C13 C14 1.397(2) . ?
C13 C16 1.443(2) . ?
C14 C15 1.376(2) . ?
C14 H14 0.95 . ?
C15 H15 0.95 . ?
C16 C17 1.178(2) . ?
C17 H17 0.95 . ?


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 C2 N8 122.99(15) . . ?
O1 C2 N3 122.67(15) . . ?
N8 C2 N3 114.34(14) . . ?
N5 N3 C2 124.69(13) . . ?
N5 N3 C4 116.06(13) . . ?
C2 N3 C4 119.20(14) . . ?
N3 C4 H4A 109.5 . . ?
N3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 N5 N3 114.66(13) . . ?
N5 C6 N7 126.96(14) . . ?
N5 C6 C10 117.11(14) . . ?
N7 C6 C10 115.93(14) . . ?
C6 N7 N8 114.85(13) . . ?
C2 N8 N7 124.41(13) . . ?
C2 N8 C9 120.72(14) . . ?
N7 N8 C9 114.87(13) . . ?
N8 C9 H9A 109.5 . . ?
N8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N8 C9 H9D 109.5 . . ?
H9A C9 H9D 141.1 . . ?
H9B C9 H9D 56.3 . . ?
H9C C9 H9D 56.3 . . ?
N8 C9 H9E 109.5 . . ?
H9A C9 H9E 56.3 . . ?
H9B C9 H9E 141.1 . . ?
H9C C9 H9E 56.3 . . ?
H9D C9 H9E 109.5 . . ?
N8 C9 H9F 109.5 . . ?
H9A C9 H9F 56.3 . . ?
H9B C9 H9F 56.3 . . ?
H9C C9 H9F 141.1 . . ?
H9D C9 H9F 109.5 . . ?
H9E C9 H9F 109.5 . . ?
C15 C10 C11 118.70(14) . . ?
C15 C10 C6 120.35(14) . . ?
C11 C10 C6 120.94(14) . . ?
C12 C11 C10 120.72(15) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C11 C12 C13 120.48(15) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C12 C13 C14 118.66(14) . . ?
C12 C13 C16 121.48(14) . . ?
C14 C13 C16 119.86(14) . . ?
C15 C14 C13 120.62(15) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C14 C15 C10 120.81(15) . . ?
C14 C15 H15 119.6 . . ?
C10 C15 H15 119.6 . . ?
C17 C16 C13 178.04(18) . . ?
C16 C17 H17 180 . . ?


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 C2 N3 N5 179.09(14) . . . . ?
N8 C2 N3 N5 -0.9(2) . . . . ?
O1 C2 N3 C4 -3.9(2) . . . . ?
N8 C2 N3 C4 176.16(13) . . . . ?
C2 N3 N5 C6 -1.7(2) . . . . ?
C4 N3 N5 C6 -178.77(13) . . . . ?
N3 N5 C6 N7 2.6(2) . . . . ?
N3 N5 C6 C10 -177.69(12) . . . . ?
N5 C6 N7 N8 -0.8(2) . . . . ?
C10 C6 N7 N8 179.49(12) . . . . ?
O1 C2 N8 N7 -177.03(14) . . . . ?
N3 C2 N8 N7 2.9(2) . . . . ?
O1 C2 N8 C9 3.2(2) . . . . ?
N3 C2 N8 C9 -176.88(14) . . . . ?
C6 N7 N8 C2 -2.2(2) . . . . ?
C6 N7 N8 C9 177.60(14) . . . . ?
N5 C6 C10 C15 -172.71(14) . . . . ?
N7 C6 C10 C15 7.1(2) . . . . ?
N5 C6 C10 C11 8.2(2) . . . . ?
N7 C6 C10 C11 -172.06(13) . . . . ?
C15 C10 C11 C12 0.1(2) . . . . ?
C6 C10 C11 C12 179.22(14) . . . . ?
C10 C11 C12 C13 -0.2(2) . . . . ?
C11 C12 C13 C14 -0.1(2) . . . . ?
C11 C12 C13 C16 179.95(14) . . . . ?
C12 C13 C14 C15 0.6(2) . . . . ?
C16 C13 C14 C15 -179.50(15) . . . . ?
C13 C14 C15 C10 -0.7(3) . . . . ?
C11 C10 C15 C14 0.4(2) . . . . ?
C6 C10 C15 C14 -178.78(15) . . . . ?
_database_code_depnum_ccdc_archive 'CCDC 1012866'
#######################################################################
#
#                 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__LN_AM_MF_100K

_audit_creation_date             2012-03-07T10:26:46-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C12 H11 N4 O'
_chemical_formula_sum            'C12 H11 N4 O'
_chemical_formula_weight         227.25
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   3.9458(2)
_cell_length_b                   11.1337(4)
_cell_length_c                   12.8406(5)
_cell_angle_alpha                105.091(2)
_cell_angle_beta                 95.100(2)
_cell_angle_gamma                93.601(2)
_cell_volume                     540.32(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5182
_cell_measurement_theta_min      2.83
_cell_measurement_theta_max      27.46
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.05
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             238
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.896
_exptl_absorpt_correction_T_max  0.995


#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_detector                 'CCD plate'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_number            6599
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.31
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_reflns_number_total             2430
_reflns_number_gt                1909
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2 (Bruker, 2006)'
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2006)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2006)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  
;
           WinGX publication routines (Farrugia, 1999),
           CRYSCAL (T. Roisnel, local program)
;

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0660P)²+0.1476P] 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_number_reflns         2430
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.047
_refine_ls_wR_factor_ref         0.1299
_refine_ls_wR_factor_gt          0.1207
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.383
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.047


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.2154(3) 0.30020(9) 0.44561(8) 0.0241(3) Uani 1 1 d . . .
C2 C 0.3303(3) 0.29133(13) 0.35858(10) 0.0185(3) Uani 1 1 d . . .
N3 N 0.4751(3) 0.18661(10) 0.30505(9) 0.0185(3) Uani 1 1 d . . .
C4 C 0.5125(4) 0.08550(13) 0.35699(11) 0.0228(3) Uani 1 1 d . . .
H4A H 0.6192 0.0179 0.3097 0.034 Uiso 1 1 calc R . .
H4B H 0.2871 0.0538 0.3699 0.034 Uiso 1 1 calc R . .
H4C H 0.6565 0.1169 0.4263 0.034 Uiso 1 1 calc R . .
N5 N 0.6025(3) 0.17133(11) 0.20706(9) 0.0191(3) Uani 1 1 d . . .
C6 C 0.5697(3) 0.26693(12) 0.16310(10) 0.0165(3) Uani 1 1 d . . .
N7 N 0.4386(3) 0.37440(11) 0.20633(9) 0.0202(3) Uani 1 1 d . . .
N8 N 0.3261(3) 0.38416(11) 0.30611(9) 0.0195(3) Uani 1 1 d . . .
C9 C 0.1960(4) 0.50369(13) 0.35533(12) 0.0255(3) Uani 1 1 d . . .
H9A H 0.2123 0.5581 0.3067 0.038 Uiso 0.5 1 calc PR . .
H9B H 0.3319 0.5436 0.4249 0.038 Uiso 0.5 1 calc PR . .
H9C H -0.0432 0.4895 0.3674 0.038 Uiso 0.5 1 calc PR . .
H9D H 0.1217 0.5026 0.4259 0.038 Uiso 0.5 1 calc PR . .
H9E H 0.0021 0.5172 0.3078 0.038 Uiso 0.5 1 calc PR . .
H9F H 0.3772 0.5713 0.3653 0.038 Uiso 0.5 1 calc PR . .
C10 C 0.6886(3) 0.25351(12) 0.05451(10) 0.0170(3) Uani 1 1 d . . .
C11 C 0.7895(3) 0.13994(12) -0.00411(11) 0.0183(3) Uani 1 1 d . . .
H11 H 0.7849 0.0706 0.0261 0.022 Uiso 1 1 calc R . .
C12 C 0.8966(3) 0.12722(13) -0.10621(10) 0.0190(3) Uani 1 1 d . . .
H12 H 0.9658 0.0495 -0.1452 0.023 Uiso 1 1 calc R . .
C13 C 0.9032(3) 0.22830(12) -0.15189(10) 0.0176(3) Uani 1 1 d . . .
C14 C 0.8000(4) 0.34213(13) -0.09291(11) 0.0218(3) Uani 1 1 d . . .
H14 H 0.8007 0.4113 -0.1234 0.026 Uiso 1 1 calc R . .
C15 C 0.6972(4) 0.35459(13) 0.00924(11) 0.0205(3) Uani 1 1 d . . .
H15 H 0.6318 0.4327 0.0489 0.025 Uiso 1 1 calc R . .
C16 C 1.0138(3) 0.21767(12) -0.25770(11) 0.0195(3) Uani 1 1 d . . .
C17 C 1.1048(4) 0.21274(13) -0.34428(12) 0.0234(3) Uani 1 1 d . . .
H17 H 1.1776 0.2088 -0.4136 0.028 Uiso 1 1 calc R . .





#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 1.2260(15) . ?
C2 N8 1.3729(18) . ?
C2 N3 1.3763(17) . ?
N3 N5 1.3698(15) . ?
N3 C4 1.4589(17) . ?
C4 H4A 0.98 . ?
C4 H4B 0.98 . ?
C4 H4C 0.98 . ?
N5 C6 1.3362(18) . ?
C6 N7 1.3380(18) . ?
C6 C10 1.4844(18) . ?
N7 N8 1.3730(15) . ?
N8 C9 1.4627(18) . ?
C9 H9A 0.98 . ?
C9 H9B 0.98 . ?
C9 H9C 0.98 . ?
C9 H9D 0.98 . ?
C9 H9E 0.98 . ?
C9 H9F 0.98 . ?
C10 C11 1.3946(19) . ?
C10 C15 1.3946(19) . ?
C11 C12 1.3881(18) . ?
C11 H11 0.95 . ?
C12 C13 1.3979(19) . ?
C12 H12 0.95 . ?
C13 C14 1.4019(19) . ?
C13 C16 1.4419(18) . ?
C14 C15 1.3825(18) . ?
C14 H14 0.95 . ?
C15 H15 0.95 . ?
C16 C17 1.1872(19) . ?
C17 H17 0.95 . ?


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 C2 N8 123.24(13) . . ?
O1 C2 N3 122.50(13) . . ?
N8 C2 N3 114.25(12) . . ?
N5 N3 C2 124.78(11) . . ?
N5 N3 C4 116.40(11) . . ?
C2 N3 C4 118.76(11) . . ?
N3 C4 H4A 109.5 . . ?
N3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 N5 N3 114.65(11) . . ?
N5 C6 N7 126.92(12) . . ?
N5 C6 C10 117.20(12) . . ?
N7 C6 C10 115.88(12) . . ?
C6 N7 N8 114.91(11) . . ?
C2 N8 N7 124.40(11) . . ?
C2 N8 C9 120.74(11) . . ?
N7 N8 C9 114.86(11) . . ?
N8 C9 H9A 109.5 . . ?
N8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N8 C9 H9D 109.5 . . ?
H9A C9 H9D 141.1 . . ?
H9B C9 H9D 56.3 . . ?
H9C C9 H9D 56.3 . . ?
N8 C9 H9E 109.5 . . ?
H9A C9 H9E 56.3 . . ?
H9B C9 H9E 141.1 . . ?
H9C C9 H9E 56.3 . . ?
H9D C9 H9E 109.5 . . ?
N8 C9 H9F 109.5 . . ?
H9A C9 H9F 56.3 . . ?
H9B C9 H9F 56.3 . . ?
H9C C9 H9F 141.1 . . ?
H9D C9 H9F 109.5 . . ?
H9E C9 H9F 109.5 . . ?
C11 C10 C15 119.09(12) . . ?
C11 C10 C6 120.76(12) . . ?
C15 C10 C6 120.15(12) . . ?
C12 C11 C10 120.64(13) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C13 120.28(13) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C12 C13 C14 118.90(12) . . ?
C12 C13 C16 121.40(12) . . ?
C14 C13 C16 119.70(12) . . ?
C15 C14 C13 120.54(13) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C14 C15 C10 120.54(13) . . ?
C14 C15 H15 119.7 . . ?
C10 C15 H15 119.7 . . ?
C17 C16 C13 178.01(15) . . ?
C16 C17 H17 180 . . ?


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 C2 N3 N5 179.00(11) . . . . ?
N8 C2 N3 N5 -0.94(19) . . . . ?
O1 C2 N3 C4 -3.9(2) . . . . ?
N8 C2 N3 C4 176.12(11) . . . . ?
C2 N3 N5 C6 -1.58(18) . . . . ?
C4 N3 N5 C6 -178.70(11) . . . . ?
N3 N5 C6 N7 2.4(2) . . . . ?
N3 N5 C6 C10 -177.28(10) . . . . ?
N5 C6 N7 N8 -0.5(2) . . . . ?
C10 C6 N7 N8 179.17(10) . . . . ?
O1 C2 N8 N7 -176.85(12) . . . . ?
N3 C2 N8 N7 3.09(19) . . . . ?
O1 C2 N8 C9 3.1(2) . . . . ?
N3 C2 N8 C9 -176.95(12) . . . . ?
C6 N7 N8 C2 -2.47(19) . . . . ?
C6 N7 N8 C9 177.57(12) . . . . ?
N5 C6 C10 C11 7.81(19) . . . . ?
N7 C6 C10 C11 -171.89(11) . . . . ?
N5 C6 C10 C15 -172.88(12) . . . . ?
N7 C6 C10 C15 7.42(19) . . . . ?
C15 C10 C11 C12 -0.1(2) . . . . ?
C6 C10 C11 C12 179.21(12) . . . . ?
C10 C11 C12 C13 -0.3(2) . . . . ?
C11 C12 C13 C14 -0.01(19) . . . . ?
C11 C12 C13 C16 179.91(12) . . . . ?
C12 C13 C14 C15 0.7(2) . . . . ?
C16 C13 C14 C15 -179.19(12) . . . . ?
C13 C14 C15 C10 -1.1(2) . . . . ?
C11 C10 C15 C14 0.8(2) . . . . ?
C6 C10 C15 C14 -178.49(12) . . . . ?



_database_code_depnum_ccdc_archive 'CCDC 1012867'
