# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2012


data_global
_journal_name_full               Chem.Commun.
_journal_coden_cambridge         0182
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_email       wwang@unm.edu
_publ_contact_author_name        'Wei Wang'
loop_
_publ_author_name
'Lu Liu'
'Deyan Wu'
'Xiangmin Li'
'Sinan Wang'
'Hao Li'
'Jian Li'
'Wei Wang'

data_cd201566
_database_code_depnum_ccdc_archive 'CCDC 853177'
#TrackingRef 'cd201566.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H10 Br N3 O2'
_chemical_formula_weight         332.16

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'
O O 0.0106 0.0060 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)

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

_cell_length_a                   8.6912(14)
_cell_length_b                   7.9895(14)
_cell_length_c                   9.7878(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.672(3)
_cell_angle_gamma                90.00
_cell_volume                     673.56(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2158
_cell_measurement_theta_min      5.891
_cell_measurement_theta_max      54.948

_exptl_crystal_description       prismatic
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.451
_exptl_crystal_size_mid          0.347
_exptl_crystal_size_min          0.269
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.638
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             332
_exptl_absorpt_coefficient_mu    3.056
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.44798
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   sadabs

_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  'CCD area detector'
_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            3680
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_av_sigmaI/netI    0.0356
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.10
_diffrn_reflns_theta_max         26.00
_reflns_number_total             2379
_reflns_number_gt                2113
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker 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^)+(0.0802P)^2^+0.0191P] 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    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_abs_structure_Flack   0.036(14)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2379
_refine_ls_number_parameters     186
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.1173
_refine_ls_wR_factor_gt          0.1150
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.001
_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 0.87960(6) -0.25943(10) -0.12112(5) 0.0759(2) Uani 1 1 d . . .
N1 N 0.8632(4) -0.0909(4) 0.4747(3) 0.0380(8) Uani 1 1 d D . .
N2 N 0.3843(4) -0.2315(6) 0.0930(4) 0.0567(11) Uani 1 1 d . . .
N3 N 0.2961(5) 0.0393(6) 0.4543(5) 0.0586(10) Uani 1 1 d . . .
O1 O 0.6814(4) 0.0602(4) 0.5724(3) 0.0457(7) Uani 1 1 d . . .
O2 O 0.8549(3) 0.2606(4) 0.3489(3) 0.0423(7) Uani 1 1 d . . .
C1 C 0.7328(5) -0.0027(5) 0.4747(4) 0.0354(8) Uani 1 1 d . . .
C2 C 0.6467(4) -0.0037(4) 0.3252(4) 0.0272(7) Uani 1 1 d . . .
C3 C 0.7630(4) -0.0897(4) 0.2475(4) 0.0296(8) Uani 1 1 d . . .
C4 C 0.8875(4) -0.1409(5) 0.3422(4) 0.0362(9) Uani 1 1 d . . .
C5 C 1.0105(4) -0.2268(5) 0.2991(5) 0.0457(10) Uani 1 1 d . . .
H5 H 1.0942 -0.2610 0.3622 0.055 Uiso 1 1 calc R . .
C6 C 1.0062(4) -0.2604(7) 0.1620(5) 0.0495(10) Uani 1 1 d . . .
H6 H 1.0870 -0.3200 0.1314 0.059 Uiso 1 1 calc R . .
C7 C 0.8828(5) -0.2066(5) 0.0679(5) 0.0439(10) Uani 1 1 d . . .
C8 C 0.7590(5) -0.1201(5) 0.1086(4) 0.0368(8) Uani 1 1 d . . .
H8 H 0.6766 -0.0841 0.0449 0.044 Uiso 1 1 calc R . .
C9 C 0.5016(4) -0.1196(5) 0.3335(4) 0.0314(8) Uani 1 1 d . . .
H9 H 0.5372 -0.2178 0.3890 0.038 Uiso 1 1 calc R . .
C10 C 0.4324(4) -0.1795(5) 0.1979(4) 0.0374(9) Uani 1 1 d . . .
C11 C 0.3841(5) -0.0337(6) 0.4035(4) 0.0396(9) Uani 1 1 d . . .
C12 C 0.5986(4) 0.1693(5) 0.2716(4) 0.0321(8) Uani 1 1 d . . .
H12A H 0.5540 0.1601 0.1757 0.039 Uiso 1 1 calc R . .
H12B H 0.5185 0.2115 0.3227 0.039 Uiso 1 1 calc R . .
C13 C 0.7298(4) 0.2940(5) 0.2828(4) 0.0334(8) Uani 1 1 d . . .
C14 C 0.6956(7) 0.4573(6) 0.2119(5) 0.0575(13) Uani 1 1 d . . .
H14A H 0.7423 0.5461 0.2692 0.086 Uiso 1 1 calc R . .
H14B H 0.5852 0.4738 0.1951 0.086 Uiso 1 1 calc R . .
H14C H 0.7371 0.4573 0.1258 0.086 Uiso 1 1 calc R . .
H1 H 0.925(4) -0.131(5) 0.536(4) 0.040(12) Uiso 1 1 d 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 0.0941(4) 0.0842(4) 0.0589(3) -0.0113(3) 0.0448(3) 0.0027(4)
N1 0.0399(17) 0.0309(17) 0.0380(18) 0.0035(14) -0.0135(15) 0.0023(15)
N2 0.0493(18) 0.076(3) 0.044(2) -0.016(2) 0.0027(16) -0.012(2)
N3 0.061(2) 0.059(2) 0.061(3) -0.008(2) 0.031(2) -0.007(2)
O1 0.0530(16) 0.0513(17) 0.0319(15) -0.0076(13) 0.0021(13) -0.0050(15)
O2 0.0399(13) 0.0413(17) 0.0453(15) 0.0016(14) 0.0042(11) -0.0038(14)
C1 0.0388(19) 0.0314(19) 0.034(2) 0.0009(15) -0.0027(16) -0.0070(16)
C2 0.0267(15) 0.0254(17) 0.0289(18) 0.0011(14) 0.0016(13) -0.0017(13)
C3 0.0305(17) 0.0238(17) 0.0336(19) 0.0021(15) 0.0007(14) -0.0050(15)
C4 0.0309(18) 0.025(2) 0.051(2) 0.0014(16) 0.0007(16) -0.0031(14)
C5 0.0327(17) 0.032(2) 0.070(3) 0.0008(19) -0.0003(18) 0.0029(17)
C6 0.0328(18) 0.038(2) 0.080(3) -0.007(3) 0.0184(19) 0.002(2)
C7 0.047(2) 0.039(2) 0.049(2) -0.0046(17) 0.0203(19) -0.0095(17)
C8 0.0383(18) 0.035(2) 0.038(2) 0.0048(16) 0.0087(16) -0.0031(16)
C9 0.0356(18) 0.0306(19) 0.0280(17) 0.0023(14) 0.0039(14) -0.0065(15)
C10 0.0337(19) 0.043(2) 0.036(2) -0.0057(17) 0.0066(16) -0.0084(16)
C11 0.042(2) 0.042(2) 0.036(2) -0.0034(17) 0.0088(18) -0.0093(18)
C12 0.0343(18) 0.0266(18) 0.036(2) 0.0048(15) 0.0049(15) 0.0017(14)
C13 0.044(2) 0.031(2) 0.0257(17) -0.0024(13) 0.0071(16) -0.0027(15)
C14 0.081(3) 0.035(2) 0.052(3) 0.0125(19) -0.007(2) -0.019(2)

_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 C7 1.894(5) . ?
N1 C1 1.334(5) . ?
N1 C4 1.399(6) . ?
N1 H1 0.817(19) . ?
N2 C10 1.135(5) . ?
N3 C11 1.129(6) . ?
O1 C1 1.217(5) . ?
O2 C13 1.219(5) . ?
C1 C2 1.552(5) . ?
C2 C3 1.509(5) . ?
C2 C12 1.517(5) . ?
C2 C9 1.576(5) . ?
C3 C8 1.377(5) . ?
C3 C4 1.390(5) . ?
C4 C5 1.382(6) . ?
C5 C6 1.364(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.386(7) . ?
C6 H6 0.9300 . ?
C7 C8 1.381(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.462(5) . ?
C9 C11 1.473(6) . ?
C9 H9 0.9800 . ?
C12 C13 1.506(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.489(6) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 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
C1 N1 C4 112.6(3) . . ?
C1 N1 H1 133(3) . . ?
C4 N1 H1 114(3) . . ?
O1 C1 N1 128.2(4) . . ?
O1 C1 C2 124.2(3) . . ?
N1 C1 C2 107.4(3) . . ?
C3 C2 C12 114.4(3) . . ?
C3 C2 C1 101.9(3) . . ?
C12 C2 C1 113.4(3) . . ?
C3 C2 C9 110.7(3) . . ?
C12 C2 C9 111.6(3) . . ?
C1 C2 C9 104.1(3) . . ?
C8 C3 C4 121.4(4) . . ?
C8 C3 C2 130.4(3) . . ?
C4 C3 C2 108.2(3) . . ?
C5 C4 C3 120.5(4) . . ?
C5 C4 N1 130.0(4) . . ?
C3 C4 N1 109.5(3) . . ?
C6 C5 C4 118.5(4) . . ?
C6 C5 H5 120.7 . . ?
C4 C5 H5 120.7 . . ?
C5 C6 C7 120.7(4) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C8 C7 C6 121.8(4) . . ?
C8 C7 Br1 118.9(3) . . ?
C6 C7 Br1 119.3(3) . . ?
C3 C8 C7 117.1(4) . . ?
C3 C8 H8 121.5 . . ?
C7 C8 H8 121.5 . . ?
C10 C9 C11 110.4(3) . . ?
C10 C9 C2 112.4(3) . . ?
C11 C9 C2 111.1(3) . . ?
C10 C9 H9 107.6 . . ?
C11 C9 H9 107.6 . . ?
C2 C9 H9 107.6 . . ?
N2 C10 C9 176.7(4) . . ?
N3 C11 C9 176.6(5) . . ?
C13 C12 C2 114.0(3) . . ?
C13 C12 H12A 108.8 . . ?
C2 C12 H12A 108.8 . . ?
C13 C12 H12B 108.8 . . ?
C2 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
O2 C13 C14 123.2(4) . . ?
O2 C13 C12 120.5(4) . . ?
C14 C13 C12 116.3(3) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

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
C4 N1 C1 O1 -178.7(4) . . . . ?
C4 N1 C1 C2 5.6(4) . . . . ?
O1 C1 C2 C3 178.0(4) . . . . ?
N1 C1 C2 C3 -6.1(4) . . . . ?
O1 C1 C2 C12 54.5(5) . . . . ?
N1 C1 C2 C12 -129.5(3) . . . . ?
O1 C1 C2 C9 -66.9(4) . . . . ?
N1 C1 C2 C9 109.1(3) . . . . ?
C12 C2 C3 C8 -53.1(5) . . . . ?
C1 C2 C3 C8 -175.8(4) . . . . ?
C9 C2 C3 C8 74.0(5) . . . . ?
C12 C2 C3 C4 127.3(3) . . . . ?
C1 C2 C3 C4 4.5(3) . . . . ?
C9 C2 C3 C4 -105.6(3) . . . . ?
C8 C3 C4 C5 -1.0(6) . . . . ?
C2 C3 C4 C5 178.7(3) . . . . ?
C8 C3 C4 N1 178.7(3) . . . . ?
C2 C3 C4 N1 -1.6(4) . . . . ?
C1 N1 C4 C5 177.0(4) . . . . ?
C1 N1 C4 C3 -2.7(5) . . . . ?
C3 C4 C5 C6 -0.2(6) . . . . ?
N1 C4 C5 C6 -179.9(4) . . . . ?
C4 C5 C6 C7 1.3(7) . . . . ?
C5 C6 C7 C8 -1.1(7) . . . . ?
C5 C6 C7 Br1 -178.8(3) . . . . ?
C4 C3 C8 C7 1.2(5) . . . . ?
C2 C3 C8 C7 -178.4(3) . . . . ?
C6 C7 C8 C3 -0.1(6) . . . . ?
Br1 C7 C8 C3 177.6(3) . . . . ?
C3 C2 C9 C10 -53.1(4) . . . . ?
C12 C2 C9 C10 75.4(4) . . . . ?
C1 C2 C9 C10 -161.9(3) . . . . ?
C3 C2 C9 C11 -177.3(3) . . . . ?
C12 C2 C9 C11 -48.8(4) . . . . ?
C1 C2 C9 C11 73.9(4) . . . . ?
C11 C9 C10 N2 -157(8) . . . . ?
C2 C9 C10 N2 79(8) . . . . ?
C10 C9 C11 N3 -90(7) . . . . ?
C2 C9 C11 N3 35(8) . . . . ?
C3 C2 C12 C13 -62.7(4) . . . . ?
C1 C2 C12 C13 53.6(4) . . . . ?
C9 C2 C12 C13 170.7(3) . . . . ?
C2 C12 C13 O2 -10.7(5) . . . . ?
C2 C12 C13 C14 170.6(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O2 0.817(19) 2.26(2) 3.043(4) 161(5) 2_746

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.590
_refine_diff_density_min         -0.642
_refine_diff_density_rms         0.070