# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is (c) The Royal Society of Chemistry 2011


data_global
_journal_name_full               Org.Biomol.Chem.
_journal_coden_cambridge         0177
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_email       duyunfeier@yahoo.com.cn
_publ_contact_author_name        'Yunfei Du'
loop_
_publ_author_name
'Zisheng Zheng'
'Lina Tang'
'Yanfeng Fan'
'Xiuxiang Qi'
'Yunfei Du'
'Daisy Zhang-Negrerie'

data_1
_database_code_depnum_ccdc_archive 'CCDC 772745'
#TrackingRef '- 1.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H13 N3'
_chemical_formula_sum            'C12 H13 N3'
_chemical_formula_weight         199.25

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           Triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.8268(18)
_cell_length_b                   8.9764(18)
_cell_length_c                   16.501(3)
_cell_angle_alpha                99.27(3)
_cell_angle_beta                 96.72(3)
_cell_angle_gamma                118.09(3)
_cell_volume                     1110.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2895
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      27.89

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.192
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             424
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.986
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_process_details   '(Jacobson, 1998)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku/MSC Mercury CCD'
_diffrn_measurement_method       \w
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8940
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_sigmaI/netI    0.0408
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.99
_diffrn_reflns_theta_max         25.20
_reflns_number_total             3982
_reflns_number_gt                2172
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'RAPID-AUTO (Rigaku, 1998)'
_computing_cell_refinement       RAPID-AUTO
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2002)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL97

_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^)+(0.1156P)^2^+0.0137P] 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_number_reflns         3982
_refine_ls_number_parameters     277
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1123
_refine_ls_R_factor_gt           0.0535
_refine_ls_wR_factor_ref         0.2100
_refine_ls_wR_factor_gt          0.1461
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1519(3) -0.0803(4) 0.09392(18) 0.0660(7) Uani 1 1 d . . .
C2 C 0.0560(4) -0.2202(4) 0.1288(2) 0.0778(9) Uani 1 1 d . . .
H2 H 0.0284 -0.3328 0.1033 0.093 Uiso 1 1 calc R . .
C3 C 0.0037(4) -0.1861(4) 0.2018(2) 0.0808(9) Uani 1 1 d . . .
H3 H -0.0598 -0.2775 0.2257 0.097 Uiso 1 1 calc R . .
C4 C 0.0433(4) -0.0189(4) 0.2408(2) 0.0771(8) Uani 1 1 d . . .
H4 H 0.0057 -0.0007 0.2899 0.093 Uiso 1 1 calc R . .
C5 C 0.1373(4) 0.1203(4) 0.20781(18) 0.0711(8) Uani 1 1 d . . .
H5 H 0.1639 0.2322 0.2338 0.085 Uiso 1 1 calc R . .
C6 C 0.1914(3) 0.0879(4) 0.13418(18) 0.0635(7) Uani 1 1 d . . .
C7 C 0.3015(3) 0.1074(4) 0.01680(18) 0.0664(7) Uani 1 1 d . . .
C8 C 0.2236(4) -0.0640(4) 0.01995(18) 0.0681(7) Uani 1 1 d . . .
C9 C 0.2163(4) -0.1991(4) -0.0417(2) 0.0796(9) Uani 1 1 d . . .
C10 C 0.2355(4) 0.4390(4) 0.0984(2) 0.0848(9) Uani 1 1 d . . .
H10A H 0.1661 0.3963 0.0419 0.127 Uiso 1 1 calc R . .
H10B H 0.2953 0.5640 0.1135 0.127 Uiso 1 1 calc R . .
H10C H 0.1601 0.3946 0.1363 0.127 Uiso 1 1 calc R . .
C11 C 0.5031(4) 0.4657(4) 0.1800(2) 0.0820(9) Uani 1 1 d . . .
H11A H 0.4517 0.4448 0.2281 0.123 Uiso 1 1 calc R . .
H11B H 0.5683 0.5888 0.1848 0.123 Uiso 1 1 calc R . .
H11C H 0.5809 0.4189 0.1776 0.123 Uiso 1 1 calc R . .
C12 C 0.3881(4) 0.1916(4) -0.0479(2) 0.0857(9) Uani 1 1 d . . .
H12A H 0.3080 0.2100 -0.0838 0.129 Uiso 1 1 calc R . .
H12B H 0.4208 0.1177 -0.0809 0.129 Uiso 1 1 calc R . .
H12C H 0.4915 0.3016 -0.0207 0.129 Uiso 1 1 calc R . .
C13 C 1.1012(4) 0.3684(4) 0.43664(17) 0.0659(7) Uani 1 1 d . . .
C14 C 1.2663(4) 0.4905(4) 0.4271(2) 0.0796(9) Uani 1 1 d . . .
H14 H 1.3684 0.5170 0.4642 0.096 Uiso 1 1 calc R . .
C15 C 1.2759(5) 0.5705(4) 0.3623(2) 0.0889(10) Uani 1 1 d . . .
H15 H 1.3848 0.6532 0.3558 0.107 Uiso 1 1 calc R . .
C16 C 1.1229(5) 0.5282(4) 0.3063(2) 0.0884(10) Uani 1 1 d . . .
H16 H 1.1322 0.5862 0.2636 0.106 Uiso 1 1 calc R . .
C17 C 0.9578(5) 0.4037(4) 0.31147(19) 0.0789(9) Uani 1 1 d . . .
H17 H 0.8571 0.3742 0.2724 0.095 Uiso 1 1 calc R . .
C18 C 0.9496(4) 0.3248(4) 0.37770(17) 0.0653(7) Uani 1 1 d . . .
C19 C 0.8629(4) 0.1649(4) 0.47435(17) 0.0653(7) Uani 1 1 d . . .
C20 C 1.0431(4) 0.2676(4) 0.49700(17) 0.0656(7) Uani 1 1 d . . .
C21 C 0.7397(4) 0.0406(4) 0.51675(19) 0.0802(9) Uani 1 1 d . . .
H21A H 0.8056 0.0232 0.5612 0.120 Uiso 1 1 calc R . .
H21B H 0.6625 -0.0688 0.4766 0.120 Uiso 1 1 calc R . .
H21C H 0.6713 0.0869 0.5399 0.120 Uiso 1 1 calc R . .
C22 C 1.1500(4) 0.2739(4) 0.56977(19) 0.0714(8) Uani 1 1 d . . .
C31 C 0.6034(5) -0.0050(5) 0.2778(2) 0.1002(11) Uani 1 1 d . . .
H31A H 0.6607 0.0680 0.2417 0.150 Uiso 1 1 calc R . .
H31B H 0.4799 -0.0766 0.2527 0.150 Uiso 1 1 calc R . .
H31C H 0.6535 -0.0778 0.2850 0.150 Uiso 1 1 calc R . .
C32 C 0.5509(4) 0.2178(5) 0.3562(2) 0.1022(12) Uani 1 1 d . . .
H32A H 0.6117 0.3018 0.3254 0.153 Uiso 1 1 calc R . .
H32B H 0.5624 0.2771 0.4124 0.153 Uiso 1 1 calc R . .
H32C H 0.4286 0.1487 0.3286 0.153 Uiso 1 1 calc R . .
N1 N 0.2845(3) 0.1994(3) 0.08636(14) 0.0664(6) Uani 1 1 d . . .
N2 N 0.3642(3) 0.3815(3) 0.10359(15) 0.0691(6) Uani 1 1 d . . .
N3 N 0.2110(4) -0.3083(4) -0.0908(2) 0.1043(10) Uani 1 1 d . . .
N4 N 0.8065(3) 0.1981(3) 0.40189(14) 0.0680(6) Uani 1 1 d . . .
N5 N 0.6279(3) 0.1037(3) 0.35957(15) 0.0763(7) Uani 1 1 d . . .
N6 N 1.2393(4) 0.2807(4) 0.62855(18) 0.0955(9) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0590(15) 0.0696(18) 0.0649(18) 0.0178(15) 0.0087(14) 0.0293(14)
C2 0.0709(18) 0.0723(19) 0.086(2) 0.0274(17) 0.0127(17) 0.0315(16)
C3 0.0683(18) 0.089(2) 0.088(2) 0.0447(19) 0.0216(17) 0.0335(17)
C4 0.0705(18) 0.093(2) 0.074(2) 0.0344(18) 0.0236(16) 0.0397(18)
C5 0.0693(17) 0.0753(19) 0.0666(19) 0.0191(16) 0.0174(15) 0.0335(16)
C6 0.0582(15) 0.0675(18) 0.0616(17) 0.0214(14) 0.0146(13) 0.0271(14)
C7 0.0581(15) 0.0735(19) 0.0590(18) 0.0146(15) 0.0107(13) 0.0272(15)
C8 0.0609(16) 0.0685(18) 0.0634(18) 0.0096(15) 0.0078(14) 0.0268(14)
C9 0.0657(18) 0.082(2) 0.078(2) 0.0052(18) 0.0075(16) 0.0333(17)
C10 0.0764(19) 0.093(2) 0.094(2) 0.0356(19) 0.0193(17) 0.0451(18)
C11 0.0700(18) 0.0752(19) 0.081(2) 0.0147(17) 0.0028(16) 0.0256(16)
C12 0.084(2) 0.105(2) 0.068(2) 0.0280(18) 0.0248(17) 0.0428(19)
C13 0.0705(18) 0.0711(18) 0.0571(17) 0.0098(14) 0.0122(14) 0.0384(15)
C14 0.075(2) 0.083(2) 0.076(2) 0.0152(17) 0.0169(16) 0.0372(17)
C15 0.092(2) 0.086(2) 0.087(2) 0.0249(19) 0.032(2) 0.0396(19)
C16 0.115(3) 0.092(2) 0.079(2) 0.0366(19) 0.038(2) 0.060(2)
C17 0.094(2) 0.092(2) 0.066(2) 0.0261(17) 0.0233(17) 0.055(2)
C18 0.0701(17) 0.0706(17) 0.0587(17) 0.0148(14) 0.0150(14) 0.0380(15)
C19 0.0733(18) 0.0771(18) 0.0533(16) 0.0161(14) 0.0119(14) 0.0440(16)
C20 0.0677(17) 0.0736(18) 0.0545(16) 0.0106(14) 0.0073(13) 0.0376(15)
C21 0.081(2) 0.092(2) 0.074(2) 0.0295(18) 0.0241(17) 0.0442(18)
C22 0.0695(18) 0.0771(19) 0.0603(18) 0.0111(15) 0.0071(15) 0.0342(16)
C31 0.095(2) 0.096(2) 0.080(2) -0.004(2) -0.0008(19) 0.037(2)
C32 0.088(2) 0.134(3) 0.105(3) 0.030(2) 0.012(2) 0.073(2)
N1 0.0681(14) 0.0615(14) 0.0626(15) 0.0177(12) 0.0174(12) 0.0255(12)
N2 0.0623(13) 0.0602(14) 0.0742(16) 0.0157(12) 0.0088(12) 0.0238(11)
N3 0.095(2) 0.105(2) 0.103(2) -0.0037(19) 0.0146(18) 0.0536(19)
N4 0.0646(14) 0.0811(15) 0.0586(14) 0.0152(12) 0.0081(11) 0.0386(13)
N5 0.0659(14) 0.0915(18) 0.0674(16) 0.0137(14) 0.0043(12) 0.0403(14)
N6 0.0931(19) 0.113(2) 0.0746(19) 0.0230(16) 0.0033(16) 0.0503(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
C1 C6 1.404(4) . ?
C1 C2 1.404(4) . ?
C1 C8 1.436(4) . ?
C2 C3 1.380(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.389(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.376(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.393(4) . ?
C5 H5 0.9300 . ?
C6 N1 1.390(3) . ?
C7 N1 1.369(3) . ?
C7 C8 1.371(4) . ?
C7 C12 1.484(4) . ?
C8 C9 1.422(4) . ?
C9 N3 1.145(4) . ?
C10 N2 1.452(4) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 N2 1.457(4) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.398(4) . ?
C13 C18 1.404(4) . ?
C13 C20 1.430(4) . ?
C14 C15 1.369(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.391(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.380(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.386(4) . ?
C17 H17 0.9300 . ?
C18 N4 1.400(3) . ?
C19 C20 1.374(4) . ?
C19 N4 1.372(3) . ?
C19 C21 1.484(4) . ?
C20 C22 1.414(4) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 N6 1.150(3) . ?
C31 N5 1.459(4) . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32 N5 1.476(4) . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
N1 N2 1.403(3) . ?
N4 N5 1.409(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
C6 C1 C2 119.3(3) . . ?
C6 C1 C8 106.2(3) . . ?
C2 C1 C8 134.5(3) . . ?
C3 C2 C1 118.2(3) . . ?
C3 C2 H2 120.9 . . ?
C1 C2 H2 120.9 . . ?
C2 C3 C4 121.8(3) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C5 C4 C3 121.0(3) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 117.8(3) . . ?
C4 C5 H5 121.1 . . ?
C6 C5 H5 121.1 . . ?
C5 C6 N1 130.9(3) . . ?
C5 C6 C1 121.8(3) . . ?
N1 C6 C1 107.2(3) . . ?
N1 C7 C8 108.0(3) . . ?
N1 C7 C12 122.1(3) . . ?
C8 C7 C12 130.0(3) . . ?
C7 C8 C9 124.2(3) . . ?
C7 C8 C1 108.5(3) . . ?
C9 C8 C1 127.4(3) . . ?
N3 C9 C8 179.5(4) . . ?
N2 C10 H10A 109.5 . . ?
N2 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N2 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N2 C11 H11A 109.5 . . ?
N2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C7 C12 H12A 109.5 . . ?
C7 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C7 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C18 119.4(3) . . ?
C14 C13 C20 134.0(3) . . ?
C18 C13 C20 106.6(3) . . ?
C15 C14 C13 119.2(3) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C14 C15 C16 120.1(3) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C17 C16 C15 122.7(3) . . ?
C17 C16 H16 118.7 . . ?
C15 C16 H16 118.7 . . ?
C16 C17 C18 116.7(3) . . ?
C16 C17 H17 121.6 . . ?
C18 C17 H17 121.6 . . ?
C17 C18 N4 131.4(3) . . ?
C17 C18 C13 121.9(3) . . ?
N4 C18 C13 106.7(2) . . ?
C20 C19 N4 107.5(3) . . ?
C20 C19 C21 129.9(3) . . ?
N4 C19 C21 122.6(3) . . ?
C19 C20 C22 124.6(3) . . ?
C19 C20 C13 108.8(2) . . ?
C22 C20 C13 126.6(3) . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N6 C22 C20 178.9(4) . . ?
N5 C31 H31A 109.5 . . ?
N5 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
N5 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
N5 C32 H32A 109.5 . . ?
N5 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
N5 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C7 N1 C6 110.2(2) . . ?
C7 N1 N2 120.8(2) . . ?
C6 N1 N2 128.9(2) . . ?
N1 N2 C10 112.1(2) . . ?
N1 N2 C11 111.6(2) . . ?
C10 N2 C11 115.7(2) . . ?
C19 N4 C18 110.4(2) . . ?
C19 N4 N5 121.1(2) . . ?
C18 N4 N5 128.4(2) . . ?
N4 N5 C31 111.0(2) . . ?
N4 N5 C32 111.8(2) . . ?
C31 N5 C32 114.1(3) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.20
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.053