# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_mo_fs264_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H8 N4'
_chemical_formula_sum            'C9 H8 N4'
_chemical_formula_weight         172.19

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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 21'

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

_cell_length_a                   7.3136(13)
_cell_length_b                   4.5404(8)
_cell_length_c                   12.823(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.900(4)
_cell_angle_gamma                90.00
_cell_volume                     413.35(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    100
_cell_measurement_reflns_used    1890
_cell_measurement_theta_min      2.87
_cell_measurement_theta_max      27.35
_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_min          0.05
_exptl_crystal_size_mid          0.102
_exptl_crystal_size_max          0.729
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             180
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9370
_exptl_absorpt_correction_T_max  0.9955

_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'

_exptl_special_details           
; 
The crystal was placed in the cold stream of an Oxford Cryosystems 
Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating 
at 100 K.
;

_diffrn_ambient_temperature      100
_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 SMART APEX II DUO CCD area-detector diffractometer 
;
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6873
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_av_sigmaI/netI    0.0246
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.64
_diffrn_reflns_theta_max         27.60
_reflns_number_total             1072
_reflns_number_gt                978
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  SHELXTL
_computing_molecular_graphics    SHELXTL
_computing_publication_material  'SHELXTL and PLATON (Spek, 2009)'

_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)+(0.0422P)²+0.0603P] 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_number_reflns         1072
_refine_ls_number_parameters     126
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0331
_refine_ls_wR_factor_ref         0.0849
_refine_ls_wR_factor_gt          0.0826
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_restrained_S_all      1.100
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.09883(19) 0.5682(4) 0.17868(10) 0.0183(4) Uani 1 1 d . . .
N2 N -0.1408(2) 0.4094(4) 0.31375(11) 0.0228(4) Uani 1 1 d . . .
N4 N -0.3281(2) 1.2320(4) -0.01712(11) 0.0210(3) Uani 1 1 d . . .
C1 C 0.1556(2) 0.3658(5) 0.25922(13) 0.0188(4) Uani 1 1 d . . .
C2 C 0.3351(2) 0.2335(5) 0.27550(13) 0.0232(4) Uani 1 1 d . . .
H2A H 0.4148 0.2810 0.2293 0.028 Uiso 1 1 calc R . .
C3 C 0.3945(3) 0.0366(5) 0.35787(14) 0.0266(4) Uani 1 1 d . . .
H3A H 0.5157 -0.0506 0.3689 0.032 Uiso 1 1 calc R . .
C4 C 0.2761(3) -0.0373(5) 0.42650(14) 0.0292(5) Uani 1 1 d . . .
H4A H 0.3191 -0.1721 0.4838 0.035 Uiso 1 1 calc R . .
C5 C 0.1006(3) 0.0831(5) 0.41116(13) 0.0261(5) Uani 1 1 d . . .
H5A H 0.0215 0.0291 0.4569 0.031 Uiso 1 1 calc R . .
C6 C 0.0362(3) 0.2878(5) 0.32749(13) 0.0205(4) Uani 1 1 d . . .
C7 C -0.1897(2) 0.6029(5) 0.23637(13) 0.0212(4) Uani 1 1 d . . .
H7A H -0.3104 0.6919 0.2251 0.025 Uiso 1 1 calc R . .
C8 C -0.0697(2) 0.6873(4) 0.16751(12) 0.0174(4) Uani 1 1 d . . .
C9 C -0.1258(2) 0.9055(4) 0.08268(13) 0.0179(4) Uani 1 1 d . . .
H9A H -0.0398 0.9592 0.0410 0.021 Uiso 1 1 calc R . .
N3 N -0.28951(18) 1.0273(4) 0.06293(11) 0.0188(4) Uani 1 1 d . . .
H2N4 H -0.270(3) 1.215(7) -0.0709(15) 0.029(6) Uiso 1 1 d . . .
H1N4 H -0.454(3) 1.292(6) -0.0367(15) 0.035(6) Uiso 1 1 d . . .


_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
N1 C8 1.322(2) . ?
N1 C1 1.370(2) . ?
N2 C7 1.309(3) . ?
N2 C6 1.379(2) . ?
N4 N3 1.363(2) . ?
N4 H2N4 0.90(2) . ?
N4 H1N4 0.93(2) . ?
C1 C2 1.413(3) . ?
C1 C6 1.422(2) . ?
C2 C3 1.372(3) . ?
C2 H2A 0.9500 . ?
C3 C4 1.416(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.365(3) . ?
C4 H4A 0.9500 . ?
C5 C6 1.412(3) . ?
C5 H5A 0.9500 . ?
C7 C8 1.439(2) . ?
C7 H7A 0.9500 . ?
C8 C9 1.456(2) . ?
C9 N3 1.288(2) . ?
C9 H9A 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 N1 C1 117.51(14) . . ?
C7 N2 C6 116.27(14) . . ?
N3 N4 H2N4 118.0(18) . . ?
N3 N4 H1N4 114.5(14) . . ?
H2N4 N4 H1N4 115.9(18) . . ?
N1 C1 C2 119.93(15) . . ?
N1 C1 C6 120.76(16) . . ?
C2 C1 C6 119.31(16) . . ?
C3 C2 C1 120.11(16) . . ?
C3 C2 H2A 119.9 . . ?
C1 C2 H2A 119.9 . . ?
C2 C3 C4 120.34(18) . . ?
C2 C3 H3A 119.8 . . ?
C4 C3 H3A 119.8 . . ?
C5 C4 C3 120.67(19) . . ?
C5 C4 H4A 119.7 . . ?
C3 C4 H4A 119.7 . . ?
C4 C5 C6 120.22(16) . . ?
C4 C5 H5A 119.9 . . ?
C6 C5 H5A 119.9 . . ?
N2 C6 C5 119.46(15) . . ?
N2 C6 C1 121.21(16) . . ?
C5 C6 C1 119.33(16) . . ?
N2 C7 C8 123.23(17) . . ?
N2 C7 H7A 118.4 . . ?
C8 C7 H7A 118.4 . . ?
N1 C8 C7 121.00(16) . . ?
N1 C8 C9 116.59(14) . . ?
C7 C8 C9 122.41(15) . . ?
N3 C9 C8 121.41(15) . . ?
N3 C9 H9A 119.3 . . ?
C8 C9 H9A 119.3 . . ?
C9 N3 N4 117.08(14) . . ?

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
C8 N1 C1 C2 -179.40(17) . . . . ?
C8 N1 C1 C6 0.2(2) . . . . ?
N1 C1 C2 C3 178.27(18) . . . . ?
C6 C1 C2 C3 -1.4(3) . . . . ?
C1 C2 C3 C4 0.5(3) . . . . ?
C2 C3 C4 C5 0.8(3) . . . . ?
C3 C4 C5 C6 -1.2(3) . . . . ?
C7 N2 C6 C5 178.37(17) . . . . ?
C7 N2 C6 C1 -1.3(3) . . . . ?
C4 C5 C6 N2 -179.41(18) . . . . ?
C4 C5 C6 C1 0.3(3) . . . . ?
N1 C1 C6 N2 1.0(3) . . . . ?
C2 C1 C6 N2 -179.34(18) . . . . ?
N1 C1 C6 C5 -178.67(17) . . . . ?
C2 C1 C6 C5 1.0(3) . . . . ?
C6 N2 C7 C8 0.5(3) . . . . ?
C1 N1 C8 C7 -1.1(2) . . . . ?
C1 N1 C8 C9 178.95(15) . . . . ?
N2 C7 C8 N1 0.8(3) . . . . ?
N2 C7 C8 C9 -179.26(17) . . . . ?
N1 C8 C9 N3 177.68(17) . . . . ?
C7 C8 C9 N3 -2.3(3) . . . . ?
C8 C9 N3 N4 179.14(16) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.60
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.038




_database_code_depnum_ccdc_archive 'CCDC 956036'
