# 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 2012


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#                                CCDC 
# 
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# 
#  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. 
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data_1
_database_code_depnum_ccdc_archive 'CCDC 889575'
#TrackingRef '120420.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H6 N10'
_chemical_formula_sum            'C4 H6 N10'
_chemical_formula_weight         194.19

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

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

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

_cell_length_a                   7.0325(17)
_cell_length_b                   9.9190(12)
_cell_length_c                   12.4750(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     870.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    291(2)
_cell_measurement_reflns_used    2537
_cell_measurement_theta_min      2.11
_cell_measurement_theta_max      23.52

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             400
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7
_exptl_absorpt_correction_T_max  0.8
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      291(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Smart Apex CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8144
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_av_sigmaI/netI    0.0222
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.27
_diffrn_reflns_theta_max         26.00
_reflns_number_total             1704
_reflns_number_gt                1649
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 2000)'
_computing_cell_refinement       SMART
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_structure_solution    'SHELXTL (Bruker, 2000)'
_computing_structure_refinement  SHELXTL
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0300P)^2^+0.1400P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(3)
_refine_ls_number_reflns         1704
_refine_ls_number_parameters     130
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0320
_refine_ls_R_factor_gt           0.0310
_refine_ls_wR_factor_ref         0.0751
_refine_ls_wR_factor_gt          0.0745
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.139
_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
N5 N 0.09522(17) 0.86215(12) 0.09337(10) 0.0435(3) Uani 1 1 d . . .
N4 N 0.24095(17) 0.90058(12) 0.02601(10) 0.0423(3) Uani 1 1 d . . .
N6 N 0.15985(18) 0.81087(12) 0.17664(10) 0.0428(3) Uani 1 1 d . . .
C1 C 0.2131(2) 0.95154(14) -0.07333(11) 0.0464(4) Uani 1 1 d . . .
N7 N 0.01508(17) 0.77273(12) 0.24495(10) 0.0422(3) Uani 1 1 d . . .
C3 C 0.0434(2) 0.70141(14) 0.33573(12) 0.0465(4) Uani 1 1 d . . .
N3 N 0.4295(2) 0.90167(15) 0.05030(11) 0.0560(3) Uani 1 1 d . . .
N8 N -0.17212(19) 0.80377(14) 0.23360(12) 0.0557(4) Uani 1 1 d . . .
N9 N -0.2514(2) 0.75023(15) 0.31654(14) 0.0652(4) Uani 1 1 d . . .
N1 N 0.3804(2) 0.98225(13) -0.11220(11) 0.0570(4) Uani 1 1 d . . .
N2 N 0.5101(2) 0.95019(16) -0.03374(13) 0.0630(4) Uani 1 1 d . . .
N10 N -0.1227(2) 0.68560(14) 0.38134(12) 0.0597(4) Uani 1 1 d . . .
C4 C 0.2292(3) 0.65073(19) 0.37371(14) 0.0631(5) Uani 1 1 d . . .
H4A H 0.2349 0.6573 0.4504 0.095 Uiso 1 1 calc R . .
H4B H 0.3293 0.7037 0.3427 0.095 Uiso 1 1 calc R . .
H4C H 0.2440 0.5582 0.3526 0.095 Uiso 1 1 calc R . .
C2 C 0.0270(3) 0.9644(2) -0.12694(14) 0.0687(5) Uani 1 1 d . . .
H2A H 0.0435 1.0073 -0.1953 0.103 Uiso 1 1 calc R . .
H2B H -0.0566 1.0178 -0.0833 0.103 Uiso 1 1 calc R . .
H2C H -0.0272 0.8765 -0.1371 0.103 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N5 0.0451(7) 0.0436(6) 0.0418(6) 0.0009(5) -0.0003(6) -0.0001(5)
N4 0.0425(6) 0.0415(6) 0.0431(6) 0.0018(5) 0.0015(5) -0.0019(5)
N6 0.0457(6) 0.0416(6) 0.0411(6) -0.0004(5) 0.0007(5) -0.0013(5)
C1 0.0578(10) 0.0397(7) 0.0418(7) 0.0008(6) 0.0040(7) 0.0000(7)
N7 0.0429(6) 0.0407(6) 0.0430(6) -0.0013(5) 0.0014(5) -0.0020(5)
C3 0.0585(9) 0.0406(7) 0.0405(7) -0.0012(6) 0.0043(7) -0.0034(6)
N3 0.0448(7) 0.0626(8) 0.0606(8) 0.0022(7) -0.0018(6) -0.0064(6)
N8 0.0449(7) 0.0585(8) 0.0638(9) 0.0043(7) 0.0049(7) 0.0047(6)
N9 0.0548(8) 0.0634(9) 0.0773(10) 0.0037(8) 0.0181(8) 0.0020(8)
N1 0.0658(9) 0.0521(8) 0.0529(8) 0.0010(6) 0.0094(7) -0.0081(7)
N2 0.0550(8) 0.0651(9) 0.0687(9) -0.0014(8) 0.0086(7) -0.0136(7)
N10 0.0676(9) 0.0541(8) 0.0574(8) 0.0051(7) 0.0181(8) -0.0017(7)
C4 0.0682(11) 0.0694(11) 0.0516(9) 0.0106(8) -0.0057(9) 0.0015(9)
C2 0.0667(11) 0.0875(13) 0.0520(9) 0.0122(10) -0.0035(9) 0.0112(10)

_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
N5 N6 1.2427(16) . ?
N5 N4 1.3790(17) . ?
N4 C1 1.3526(18) . ?
N4 N3 1.3603(19) . ?
N6 N7 1.3805(17) . ?
C1 N1 1.308(2) . ?
C1 C2 1.476(2) . ?
N7 C3 1.3500(19) . ?
N7 N8 1.3594(18) . ?
C3 N10 1.308(2) . ?
C3 C4 1.478(2) . ?
N3 N2 1.2851(19) . ?
N8 N9 1.290(2) . ?
N9 N10 1.373(2) . ?
N1 N2 1.375(2) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?

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
N6 N5 N4 110.53(12) . . ?
C1 N4 N3 110.01(12) . . ?
C1 N4 N5 123.64(12) . . ?
N3 N4 N5 126.22(12) . . ?
N5 N6 N7 111.01(12) . . ?
N1 C1 N4 107.25(14) . . ?
N1 C1 C2 127.55(14) . . ?
N4 C1 C2 125.16(14) . . ?
C3 N7 N8 110.42(13) . . ?
C3 N7 N6 123.55(13) . . ?
N8 N7 N6 126.00(13) . . ?
N10 C3 N7 107.21(14) . . ?
N10 C3 C4 127.51(14) . . ?
N7 C3 C4 125.28(14) . . ?
N2 N3 N4 104.53(13) . . ?
N9 N8 N7 103.99(14) . . ?
N8 N9 N10 112.32(13) . . ?
C1 N1 N2 106.18(13) . . ?
N3 N2 N1 112.02(14) . . ?
C3 N10 N9 106.06(13) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.110
_refine_diff_density_min         -0.109
_refine_diff_density_rms         0.028