# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is (c) The Royal Society of Chemistry 2010

data_global2
_journal_name_full               Org.Biomol.Chem.

_journal_coden_Cambridge         0177

_publ_contact_author_name        'Xie, Jian-Wu'
_publ_contact_author_email       xiejw@zjnu.cn

_publ_section_title              
;
The Organocatalytic Two-step Synthesis of
Diversely Functionalized Tricyclic Tetrazoles
;
loop_
_publ_author_name
'Jian-Wu Xie'
'Xiong Huang'
'Ping Li'
'Xin-Sheng Li'
'Dong-Cheng Xu'

# Attachment '- 4g.CIF'

#==============================================================================

data_a
_database_code_depnum_ccdc_archive 'CCDC 773011'
#TrackingRef '- 4g.CIF'

_audit_update_record             
;
2010-04-13 # Formatted by publCIF
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H12 Br N5 O'
_chemical_formula_sum            'C18 H12 Br N5 O'
_chemical_formula_weight         394.24

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'
Br Br -0.2901 2.4595 '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           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   6.760(3)
_cell_length_b                   7.753(4)
_cell_length_c                   15.097(7)
_cell_angle_alpha                85.324(18)
_cell_angle_beta                 83.591(17)
_cell_angle_gamma                77.658(17)
_cell_volume                     766.8(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1279
_cell_measurement_theta_min      2.69
_cell_measurement_theta_max      29.93

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          .268
_exptl_crystal_size_mid          .104
_exptl_crystal_size_min          .054
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.708
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             396
_exptl_absorpt_coefficient_mu    2.698
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_absorpt_correction_T_min  .721
_exptl_absorpt_correction_T_max  .864

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      296(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  'Bruker APEXII area-detector diffractometer'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        0
_diffrn_reflns_number            9543
_diffrn_reflns_av_R_equivalents  0.1178
_diffrn_reflns_av_sigmaI/netI    0.1978
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.69
_diffrn_reflns_theta_max         29.93
_reflns_number_total             3590
_reflns_number_gt                1294
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEXII (Bruker, 2006)'
_computing_cell_refinement       'SAINT (Bruker, 2006)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_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^)+(0.0704P)^2^+0.0000P] 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     SHELXL
_refine_ls_extinction_coef       0.020(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         3590
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_ref          0.2236
_refine_ls_R_factor_gt           0.0714
_refine_ls_wR_factor_ref         0.1976
_refine_ls_wR_factor_gt          0.1543
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_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
Br1 Br 0.77256(14) 0.10451(11) 0.58639(6) 0.0732(4) Uani 1 1 d . . .
C1 C 0.2702(13) 0.3344(10) 0.4702(5) 0.067(2) Uani 1 1 d . . .
H1A H 0.1313 0.3592 0.4879 0.081 Uiso 1 1 calc R . .
C2 C 0.3970(13) 0.2528(11) 0.5293(6) 0.069(2) Uani 1 1 d . . .
H2A H 0.3467 0.2199 0.5867 0.083 Uiso 1 1 calc R . .
C3 C 0.5949(12) 0.2191(9) 0.5056(5) 0.0537(19) Uani 1 1 d . . .
C4 C 0.6671(13) 0.2661(10) 0.4220(6) 0.069(2) Uani 1 1 d . . .
H4A H 0.8065 0.2411 0.4055 0.083 Uiso 1 1 calc R . .
C5 C 0.5412(13) 0.3473(11) 0.3633(6) 0.069(2) Uani 1 1 d . . .
H5A H 0.5924 0.3808 0.3062 0.082 Uiso 1 1 calc R . .
C6 C 0.3346(11) 0.3821(8) 0.3868(5) 0.0470(18) Uani 1 1 d . . .
C7 C 0.1873(11) 0.4759(8) 0.3265(5) 0.0465(18) Uani 1 1 d . . .
C8 C 0.2536(10) 0.5526(8) 0.2396(5) 0.0432(17) Uani 1 1 d . . .
H8A H 0.3470 0.4609 0.2070 0.052 Uiso 1 1 calc R . .
H8B H 0.3279 0.6426 0.2489 0.052 Uiso 1 1 calc R . .
C9 C 0.0887(10) 0.6318(8) 0.1844(5) 0.0446(17) Uani 1 1 d . . .
H9A H 0.0040 0.5443 0.1828 0.053 Uiso 1 1 calc R . .
C10 C 0.1631(9) 0.6744(8) 0.0922(4) 0.0399(16) Uani 1 1 d . . .
C11 C 0.2071(10) 0.5511(9) 0.0299(5) 0.0473(18) Uani 1 1 d . . .
H11A H 0.1823 0.4385 0.0453 0.057 Uiso 1 1 calc R . .
C12 C 0.2853(11) 0.5882(11) -0.0531(5) 0.055(2) Uani 1 1 d . . .
H12A H 0.3121 0.5018 -0.0945 0.066 Uiso 1 1 calc R . .
C13 C 0.3262(10) 0.7508(10) -0.0777(5) 0.055(2) Uani 1 1 d . . .
H13A H 0.3854 0.7744 -0.1348 0.066 Uiso 1 1 calc R . .
C14 C 0.2802(11) 0.8759(10) -0.0187(5) 0.0523(19) Uani 1 1 d . . .
H14A H 0.3044 0.9883 -0.0350 0.063 Uiso 1 1 calc R . .
C15 C 0.1991(10) 0.8396(9) 0.0641(5) 0.0454(17) Uani 1 1 d . . .
C16 C 0.0356(11) 0.9529(9) 0.2030(5) 0.0473(18) Uani 1 1 d . . .
C17 C -0.0472(10) 0.7957(8) 0.2282(5) 0.0436(17) Uani 1 1 d . . .
H17A H -0.0498 0.7744 0.2932 0.052 Uiso 1 1 calc R . .
C18 C -0.2540(12) 0.8212(9) 0.2045(5) 0.053(2) Uani 1 1 d . . .
N1 N 0.0154(9) 1.0938(8) 0.2443(4) 0.0558(17) Uani 1 1 d . . .
N2 N 0.1199(10) 1.1950(8) 0.1921(5) 0.0634(19) Uani 1 1 d . . .
N3 N 0.2014(9) 1.1189(7) 0.1203(4) 0.0557(16) Uani 1 1 d . . .
N4 N 0.1466(8) 0.9652(7) 0.1278(4) 0.0450(15) Uani 1 1 d . . .
N5 N -0.4097(11) 0.8287(9) 0.1875(5) 0.074(2) Uani 1 1 d . . .
O1 O 0.0087(8) 0.4878(6) 0.3488(4) 0.0603(14) 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
Br1 0.0803(7) 0.0724(6) 0.0638(7) -0.0010(4) -0.0237(5) -0.0017(5)
C1 0.064(5) 0.083(6) 0.046(5) 0.013(5) 0.001(5) -0.006(5)
C2 0.057(6) 0.093(6) 0.042(5) 0.020(4) 0.000(4) 0.007(5)
C3 0.068(6) 0.042(4) 0.049(5) 0.008(4) -0.018(4) -0.004(4)
C4 0.053(5) 0.082(6) 0.068(6) 0.031(5) -0.011(5) -0.015(5)
C5 0.062(6) 0.090(6) 0.047(5) 0.021(5) 0.000(5) -0.014(5)
C6 0.054(5) 0.040(4) 0.045(5) 0.004(3) -0.006(4) -0.008(4)
C7 0.049(5) 0.042(4) 0.046(5) 0.002(4) -0.011(4) -0.001(4)
C8 0.043(4) 0.035(4) 0.050(5) 0.001(3) -0.002(4) -0.007(3)
C9 0.043(4) 0.037(4) 0.053(5) -0.001(3) -0.001(4) -0.009(3)
C10 0.040(4) 0.042(4) 0.038(4) 0.000(3) -0.005(3) -0.009(3)
C11 0.046(4) 0.039(4) 0.057(5) -0.006(4) -0.012(4) -0.006(3)
C12 0.056(5) 0.060(5) 0.048(5) -0.012(4) -0.003(4) -0.010(4)
C13 0.048(5) 0.069(5) 0.044(5) -0.001(4) 0.002(4) -0.006(4)
C14 0.052(4) 0.055(4) 0.048(5) 0.010(4) 0.001(4) -0.015(4)
C15 0.040(4) 0.044(4) 0.052(5) 0.003(4) -0.010(4) -0.006(3)
C16 0.046(4) 0.043(4) 0.053(5) -0.009(4) -0.005(4) -0.005(3)
C17 0.046(4) 0.038(4) 0.045(4) 0.002(3) -0.009(3) -0.002(3)
C18 0.044(5) 0.039(4) 0.074(6) -0.004(4) -0.001(4) -0.005(4)
N1 0.067(4) 0.038(3) 0.061(4) -0.005(3) -0.006(3) -0.008(3)
N2 0.069(4) 0.039(4) 0.083(5) -0.007(4) -0.013(4) -0.007(3)
N3 0.063(4) 0.038(3) 0.068(5) 0.003(3) -0.002(3) -0.019(3)
N4 0.044(3) 0.032(3) 0.059(4) -0.005(3) -0.006(3) -0.007(3)
N5 0.047(4) 0.069(5) 0.102(6) 0.012(4) -0.004(4) -0.011(4)
O1 0.048(3) 0.057(3) 0.070(4) 0.011(3) 0.002(3) -0.007(3)

_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
Br1 C3 1.848(7) . ?
C1 C2 1.333(11) . ?
C1 C6 1.336(10) . ?
C1 H1A 0.9300 . ?
C2 C3 1.321(11) . ?
C2 H2A 0.9300 . ?
C3 C4 1.352(11) . ?
C4 C5 1.324(11) . ?
C4 H4A 0.9300 . ?
C5 C6 1.376(10) . ?
C5 H5A 0.9300 . ?
C6 C7 1.461(10) . ?
C7 O1 1.202(8) . ?
C7 C8 1.460(9) . ?
C8 C9 1.464(9) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.462(9) . ?
C9 C17 1.548(8) . ?
C9 H9A 0.9800 . ?
C10 C11 1.361(8) . ?
C10 C15 1.379(9) . ?
C11 C12 1.338(10) . ?
C11 H11A 0.9300 . ?
C12 C13 1.361(10) . ?
C12 H12A 0.9300 . ?
C13 C14 1.334(9) . ?
C13 H13A 0.9300 . ?
C14 C15 1.341(9) . ?
C14 H14A 0.9300 . ?
C15 N4 1.387(8) . ?
C16 N1 1.276(7) . ?
C16 N4 1.298(8) . ?
C16 C17 1.453(9) . ?
C17 C18 1.450(10) . ?
C17 H17A 0.9800 . ?
C18 N5 1.099(8) . ?
N1 N2 1.321(8) . ?
N2 N3 1.288(8) . ?
N3 N4 1.315(7) . ?

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
C2 C1 C6 122.7(8) . . ?
C2 C1 H1A 118.7 . . ?
C6 C1 H1A 118.7 . . ?
C3 C2 C1 119.3(8) . . ?
C3 C2 H2A 120.4 . . ?
C1 C2 H2A 120.4 . . ?
C2 C3 C4 120.1(8) . . ?
C2 C3 Br1 119.8(7) . . ?
C4 C3 Br1 120.1(6) . . ?
C5 C4 C3 120.6(8) . . ?
C5 C4 H4A 119.7 . . ?
C3 C4 H4A 119.7 . . ?
C4 C5 C6 120.0(9) . . ?
C4 C5 H5A 120.0 . . ?
C6 C5 H5A 120.0 . . ?
C1 C6 C5 117.3(7) . . ?
C1 C6 C7 119.6(7) . . ?
C5 C6 C7 123.0(7) . . ?
O1 C7 C8 119.8(7) . . ?
O1 C7 C6 119.1(7) . . ?
C8 C7 C6 121.1(6) . . ?
C7 C8 C9 114.6(6) . . ?
C7 C8 H8A 108.6 . . ?
C9 C8 H8A 108.6 . . ?
C7 C8 H8B 108.6 . . ?
C9 C8 H8B 108.6 . . ?
H8A C8 H8B 107.6 . . ?
C10 C9 C8 112.6(6) . . ?
C10 C9 C17 111.7(6) . . ?
C8 C9 C17 110.1(5) . . ?
C10 C9 H9A 107.4 . . ?
C8 C9 H9A 107.4 . . ?
C17 C9 H9A 107.4 . . ?
C11 C10 C15 116.1(7) . . ?
C11 C10 C9 121.7(6) . . ?
C15 C10 C9 122.1(6) . . ?
C12 C11 C10 121.4(7) . . ?
C12 C11 H11A 119.3 . . ?
C10 C11 H11A 119.3 . . ?
C11 C12 C13 120.9(6) . . ?
C11 C12 H12A 119.5 . . ?
C13 C12 H12A 119.5 . . ?
C14 C13 C12 119.0(7) . . ?
C14 C13 H13A 120.5 . . ?
C12 C13 H13A 120.5 . . ?
C13 C14 C15 120.1(7) . . ?
C13 C14 H14A 119.9 . . ?
C15 C14 H14A 119.9 . . ?
C14 C15 C10 122.3(6) . . ?
C14 C15 N4 122.5(7) . . ?
C10 C15 N4 115.3(7) . . ?
N1 C16 N4 109.7(6) . . ?
N1 C16 C17 129.8(7) . . ?
N4 C16 C17 120.5(6) . . ?
C18 C17 C16 110.9(6) . . ?
C18 C17 C9 110.5(5) . . ?
C16 C17 C9 110.9(6) . . ?
C18 C17 H17A 108.2 . . ?
C16 C17 H17A 108.2 . . ?
C9 C17 H17A 108.2 . . ?
N5 C18 C17 175.3(8) . . ?
C16 N1 N2 105.3(6) . . ?
N3 N2 N1 111.3(5) . . ?
N2 N3 N4 104.9(6) . . ?
C16 N4 N3 108.8(5) . . ?
C16 N4 C15 126.6(6) . . ?
N3 N4 C15 124.6(6) . . ?

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 C3 1.0(13) . . . . ?
C1 C2 C3 C4 -0.5(12) . . . . ?
C1 C2 C3 Br1 -179.5(6) . . . . ?
C2 C3 C4 C5 0.6(12) . . . . ?
Br1 C3 C4 C5 179.6(6) . . . . ?
C3 C4 C5 C6 -1.1(13) . . . . ?
C2 C1 C6 C5 -1.4(12) . . . . ?
C2 C1 C6 C7 -178.2(7) . . . . ?
C4 C5 C6 C1 1.4(11) . . . . ?
C4 C5 C6 C7 178.1(7) . . . . ?
C1 C6 C7 O1 -9.9(10) . . . . ?
C5 C6 C7 O1 173.5(7) . . . . ?
C1 C6 C7 C8 171.0(6) . . . . ?
C5 C6 C7 C8 -5.6(10) . . . . ?
O1 C7 C8 C9 -3.0(9) . . . . ?
C6 C7 C8 C9 176.1(5) . . . . ?
C7 C8 C9 C10 -168.5(5) . . . . ?
C7 C8 C9 C17 66.1(7) . . . . ?
C8 C9 C10 C11 84.0(7) . . . . ?
C17 C9 C10 C11 -151.5(6) . . . . ?
C8 C9 C10 C15 -93.8(7) . . . . ?
C17 C9 C10 C15 30.7(8) . . . . ?
C15 C10 C11 C12 1.5(9) . . . . ?
C9 C10 C11 C12 -176.4(7) . . . . ?
C10 C11 C12 C13 0.9(11) . . . . ?
C11 C12 C13 C14 -2.5(11) . . . . ?
C12 C13 C14 C15 1.5(11) . . . . ?
C13 C14 C15 C10 1.0(11) . . . . ?
C13 C14 C15 N4 -179.4(6) . . . . ?
C11 C10 C15 C14 -2.5(10) . . . . ?
C9 C10 C15 C14 175.4(6) . . . . ?
C11 C10 C15 N4 177.8(5) . . . . ?
C9 C10 C15 N4 -4.2(9) . . . . ?
N1 C16 C17 C18 83.1(9) . . . . ?
N4 C16 C17 C18 -95.8(8) . . . . ?
N1 C16 C17 C9 -153.8(7) . . . . ?
N4 C16 C17 C9 27.4(9) . . . . ?
C10 C9 C17 C18 83.0(7) . . . . ?
C8 C9 C17 C18 -151.1(6) . . . . ?
C10 C9 C17 C16 -40.3(7) . . . . ?
C8 C9 C17 C16 85.6(7) . . . . ?
N4 C16 N1 N2 -0.5(8) . . . . ?
C17 C16 N1 N2 -179.5(7) . . . . ?
C16 N1 N2 N3 0.4(8) . . . . ?
N1 N2 N3 N4 -0.1(8) . . . . ?
N1 C16 N4 N3 0.5(8) . . . . ?
C17 C16 N4 N3 179.6(6) . . . . ?
N1 C16 N4 C15 -178.9(6) . . . . ?
C17 C16 N4 C15 0.2(10) . . . . ?
N2 N3 N4 C16 -0.2(7) . . . . ?
N2 N3 N4 C15 179.2(6) . . . . ?
C14 C15 N4 C16 166.7(7) . . . . ?
C10 C15 N4 C16 -13.6(10) . . . . ?
C14 C15 N4 N3 -12.5(10) . . . . ?
C10 C15 N4 N3 167.1(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.808
_diffrn_reflns_theta_full        29.93
_diffrn_measured_fraction_theta_full 0.808
_refine_diff_density_max         0.982
_refine_diff_density_min         -1.097
_refine_diff_density_rms         0.169