# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2012


data_global
_journal_name_full               Org.Biomol.Chem.
_journal_coden_cambridge         0177
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
loop_
_publ_author_name
'Yang Jia'
'Wen Yang'
'Da-Ming Du'
_publ_contact_author_name        'Da-Ming Du'
_publ_contact_author_email       dudm@bit.edu.cn

data_bo1447
_database_code_depnum_ccdc_archive 'CCDC 868579'
#TrackingRef '- BO1447.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H13 Br N2 O3'
_chemical_formula_weight         373.20

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           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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                   9.315(3)
_cell_length_b                   10.631(4)
_cell_length_c                   15.819(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1566.5(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    5829
_cell_measurement_theta_min      2.308
_cell_measurement_theta_max      29.117

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.26
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.582
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752
_exptl_absorpt_coefficient_mu    2.640
_exptl_absorpt_correction_type   Multi-scans
_exptl_absorpt_correction_T_min  0.3999
_exptl_absorpt_correction_T_max  0.5491
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  AFC10/Saturn724+
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            13727
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_av_sigmaI/netI    0.0748
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.18
_diffrn_reflns_theta_max         29.12
_reflns_number_total             4196
_reflns_number_gt                2771
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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^)+(0.0011P)^2^+-0.1000P] 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       ?
_chemical_absolute_configuration ad
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.011(4)
_refine_ls_number_reflns         4196
_refine_ls_number_parameters     222
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0291
_refine_ls_wR_factor_ref         0.0377
_refine_ls_wR_factor_gt          0.0367
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_restrained_S_all      0.989
_refine_ls_shift/su_max          0.003
_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
O1 O 0.94140(14) 0.62012(13) 0.67808(8) 0.0210(4) Uani 1 1 d . . .
O2 O 1.11151(17) 0.52191(15) 0.86761(10) 0.0401(5) Uani 1 1 d . . .
O3 O 1.11902(15) 0.40688(14) 0.75539(10) 0.0313(4) Uani 1 1 d . . .
N1 N 0.4347(2) 0.39219(19) 0.78308(11) 0.0226(5) Uani 1 1 d . A .
N2 N 1.0541(2) 0.46824(17) 0.80829(11) 0.0233(5) Uani 1 1 d . A .
C1 C 0.9038(2) 0.5236(2) 0.62290(14) 0.0170(5) Uani 1 1 d . A .
C2 C 0.9316(2) 0.5444(2) 0.53799(13) 0.0223(6) Uani 1 1 d . . .
H2 H 0.9729 0.6217 0.5201 0.027 Uiso 1 1 calc R . .
C3 C 0.8990(2) 0.4521(2) 0.47946(13) 0.0283(6) Uani 1 1 d . A .
H3 H 0.9193 0.4648 0.4212 0.034 Uiso 1 1 calc R . .
C4 C 0.8369(2) 0.34179(17) 0.50636(11) 0.0266(6) Uani 1 1 d D . .
C5 C 0.8105(2) 0.31985(17) 0.59095(11) 0.0226(5) Uani 1 1 d . A .
H5 H 0.7678 0.2429 0.6081 0.027 Uiso 1 1 calc R . .
C6 C 0.8464(2) 0.41024(19) 0.65133(12) 0.0168(5) Uani 1 1 d . . .
C7 C 0.82567(18) 0.38118(18) 0.74424(11) 0.0152(5) Uani 1 1 d . A .
H7 H 0.8767 0.3006 0.7569 0.018 Uiso 1 1 calc R . .
C8 C 0.8935(2) 0.48475(18) 0.79801(12) 0.0166(5) Uani 1 1 d . . .
H8 H 0.8477 0.4843 0.8552 0.020 Uiso 1 1 calc R A .
C9 C 0.8725(2) 0.61309(17) 0.75848(12) 0.0208(5) Uani 1 1 d . A .
H9A H 0.7686 0.6297 0.7516 0.025 Uiso 1 1 calc R . .
H9B H 0.9125 0.6784 0.7964 0.025 Uiso 1 1 calc R . .
C10 C 0.5551(2) 0.4296(2) 0.74051(13) 0.0220(5) Uani 1 1 d . A .
H10 H 0.5571 0.4913 0.6971 0.026 Uiso 1 1 calc R . .
C11 C 0.6713(2) 0.36562(18) 0.76923(11) 0.0157(5) Uani 1 1 d . . .
C12 C 0.6210(2) 0.2807(2) 0.83382(11) 0.0155(5) Uani 1 1 d . A .
C13 C 0.6851(2) 0.19183(17) 0.88578(11) 0.0200(5) Uani 1 1 d . . .
H13 H 0.7857 0.1777 0.8826 0.024 Uiso 1 1 calc R A .
C14 C 0.6022(2) 0.12389(19) 0.94218(12) 0.0246(5) Uani 1 1 d . A .
H14 H 0.6461 0.0629 0.9777 0.030 Uiso 1 1 calc R . .
C15 C 0.4533(2) 0.1446(2) 0.94729(12) 0.0260(6) Uani 1 1 d . . .
H15 H 0.3981 0.0964 0.9860 0.031 Uiso 1 1 calc R A .
C16 C 0.3858(2) 0.2325(2) 0.89772(11) 0.0234(5) Uani 1 1 d . A .
H16 H 0.2855 0.2470 0.9020 0.028 Uiso 1 1 calc R . .
C17 C 0.4710(2) 0.3000(2) 0.84045(11) 0.0177(5) Uani 1 1 d . . .
H1N H 0.349(2) 0.4240(19) 0.7716(13) 0.055(9) Uiso 1 1 d . . .
Br1 Br 0.8048(13) 0.2155(3) 0.4241(3) 0.0658(9) Uani 0.60(2) 1 d PD A 1
Br1' Br 0.7710(6) 0.2153(5) 0.4301(3) 0.0387(9) Uani 0.40(2) 1 d PD A 2

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
O1 0.0234(9) 0.0163(9) 0.0234(9) 0.0035(7) 0.0037(7) -0.0022(7)
O2 0.0346(11) 0.0488(13) 0.0370(11) -0.0077(9) -0.0174(9) -0.0072(9)
O3 0.0172(9) 0.0373(12) 0.0395(11) -0.0099(9) 0.0001(8) 0.0038(8)
N1 0.0111(12) 0.0317(13) 0.0251(11) 0.0035(9) -0.0032(9) 0.0029(10)
N2 0.0209(12) 0.0231(13) 0.0259(13) 0.0061(10) -0.0041(10) -0.0035(10)
C1 0.0124(13) 0.0223(14) 0.0163(13) 0.0002(10) 0.0004(10) 0.0027(10)
C2 0.0207(14) 0.0213(14) 0.0248(13) 0.0103(11) 0.0052(10) 0.0017(11)
C3 0.0343(16) 0.0360(16) 0.0147(12) 0.0067(11) 0.0015(11) 0.0100(14)
C4 0.0402(17) 0.0204(13) 0.0193(13) -0.0035(10) -0.0054(11) 0.0120(12)
C5 0.0280(14) 0.0160(12) 0.0239(13) 0.0022(9) -0.0016(10) 0.0015(11)
C6 0.0150(13) 0.0170(13) 0.0182(12) 0.0023(10) -0.0003(9) 0.0022(10)
C7 0.0146(12) 0.0157(12) 0.0155(11) 0.0056(9) 0.0035(10) 0.0014(9)
C8 0.0083(12) 0.0216(13) 0.0198(13) 0.0028(10) 0.0044(10) 0.0015(10)
C9 0.0195(12) 0.0233(14) 0.0195(12) -0.0027(11) 0.0014(10) 0.0024(10)
C10 0.0198(13) 0.0275(15) 0.0187(13) 0.0051(11) -0.0002(11) -0.0046(11)
C11 0.0143(12) 0.0200(12) 0.0130(11) 0.0011(9) -0.0008(9) -0.0017(10)
C12 0.0144(12) 0.0176(11) 0.0145(10) -0.0014(11) -0.0015(9) -0.0023(12)
C13 0.0200(13) 0.0209(13) 0.0190(11) -0.0011(9) -0.0004(10) 0.0018(11)
C14 0.0377(15) 0.0181(13) 0.0180(13) 0.0012(10) 0.0011(11) -0.0022(12)
C15 0.0341(15) 0.0274(14) 0.0166(13) -0.0027(11) 0.0068(11) -0.0116(12)
C16 0.0197(12) 0.0315(15) 0.0189(11) -0.0054(11) 0.0046(10) -0.0081(12)
C17 0.0185(13) 0.0195(13) 0.0152(11) -0.0038(11) -0.0016(9) -0.0062(11)
Br1 0.140(3) 0.0325(7) 0.0251(6) -0.0102(6) -0.0149(13) 0.0203(11)
Br1' 0.062(3) 0.0331(9) 0.0211(8) -0.0041(8) -0.0082(6) 0.0013(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
O1 C1 1.392(2) . ?
O1 C9 1.427(2) . ?
O2 N2 1.221(2) . ?
O3 N2 1.221(2) . ?
N1 C10 1.367(2) . ?
N1 C17 1.378(3) . ?
N1 H1N 0.889(19) . ?
N2 C8 1.515(2) . ?
C1 C2 1.386(3) . ?
C1 C6 1.393(3) . ?
C2 C3 1.383(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.375(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.380(2) . ?
C4 Br1 1.894(2) . ?
C4 Br1' 1.908(3) . ?
C5 C6 1.395(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.514(2) . ?
C7 C11 1.500(2) . ?
C7 C8 1.528(2) . ?
C7 H7 1.0000 . ?
C8 C9 1.514(2) . ?
C8 H8 1.0000 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.357(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.442(2) . ?
C12 C13 1.387(2) . ?
C12 C17 1.417(2) . ?
C13 C14 1.383(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.407(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.373(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.402(2) . ?
C16 H16 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
C1 O1 C9 114.03(15) . . ?
C10 N1 C17 109.27(18) . . ?
C10 N1 H1N 122.0(14) . . ?
C17 N1 H1N 128.7(13) . . ?
O3 N2 O2 124.0(2) . . ?
O3 N2 C8 118.50(17) . . ?
O2 N2 C8 117.41(18) . . ?
C2 C1 O1 116.3(2) . . ?
C2 C1 C6 121.5(2) . . ?
O1 C1 C6 122.14(19) . . ?
C3 C2 C1 119.6(2) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C4 C3 C2 119.37(19) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 121.27(17) . . ?
C3 C4 Br1 117.3(3) . . ?
C5 C4 Br1 121.2(3) . . ?
C3 C4 Br1' 122.7(2) . . ?
C5 C4 Br1' 115.9(2) . . ?
Br1 C4 Br1' 9.9(3) . . ?
C4 C5 C6 120.31(18) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 117.81(19) . . ?
C1 C6 C7 122.60(18) . . ?
C5 C6 C7 119.57(18) . . ?
C11 C7 C6 113.60(16) . . ?
C11 C7 C8 109.21(15) . . ?
C6 C7 C8 109.91(16) . . ?
C11 C7 H7 108.0 . . ?
C6 C7 H7 108.0 . . ?
C8 C7 H7 108.0 . . ?
C9 C8 N2 106.06(15) . . ?
C9 C8 C7 111.47(16) . . ?
N2 C8 C7 112.62(16) . . ?
C9 C8 H8 108.9 . . ?
N2 C8 H8 108.9 . . ?
C7 C8 H8 108.9 . . ?
O1 C9 C8 110.93(15) . . ?
O1 C9 H9A 109.5 . . ?
C8 C9 H9A 109.5 . . ?
O1 C9 H9B 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 108.0 . . ?
C11 C10 N1 110.13(19) . . ?
C11 C10 H10 124.9 . . ?
N1 C10 H10 124.9 . . ?
C10 C11 C12 106.95(17) . . ?
C10 C11 C7 128.42(19) . . ?
C12 C11 C7 124.56(17) . . ?
C13 C12 C17 118.66(19) . . ?
C13 C12 C11 134.95(19) . . ?
C17 C12 C11 106.39(18) . . ?
C14 C13 C12 119.84(19) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C13 C14 C15 120.4(2) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C16 C15 C14 121.7(2) . . ?
C16 C15 H15 119.2 . . ?
C14 C15 H15 119.2 . . ?
C15 C16 C17 117.3(2) . . ?
C15 C16 H16 121.4 . . ?
C17 C16 H16 121.4 . . ?
N1 C17 C16 130.6(2) . . ?
N1 C17 C12 107.24(18) . . ?
C16 C17 C12 122.1(2) . . ?

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
C9 O1 C1 C2 161.42(17) . . . . ?
C9 O1 C1 C6 -20.9(3) . . . . ?
O1 C1 C2 C3 179.14(17) . . . . ?
C6 C1 C2 C3 1.4(3) . . . . ?
C1 C2 C3 C4 1.2(3) . . . . ?
C2 C3 C4 C5 -2.0(3) . . . . ?
C2 C3 C4 Br1 -176.5(4) . . . . ?
C2 C3 C4 Br1' 173.9(3) . . . . ?
C3 C4 C5 C6 0.2(3) . . . . ?
Br1 C4 C5 C6 174.5(4) . . . . ?
Br1' C4 C5 C6 -175.9(2) . . . . ?
C2 C1 C6 C5 -3.2(3) . . . . ?
O1 C1 C6 C5 179.24(17) . . . . ?
C2 C1 C6 C7 175.15(19) . . . . ?
O1 C1 C6 C7 -2.4(3) . . . . ?
C4 C5 C6 C1 2.4(3) . . . . ?
C4 C5 C6 C7 -176.02(17) . . . . ?
C1 C6 C7 C11 115.5(2) . . . . ?
C5 C6 C7 C11 -66.1(2) . . . . ?
C1 C6 C7 C8 -7.2(3) . . . . ?
C5 C6 C7 C8 171.16(17) . . . . ?
O3 N2 C8 C9 -98.9(2) . . . . ?
O2 N2 C8 C9 78.2(2) . . . . ?
O3 N2 C8 C7 23.3(3) . . . . ?
O2 N2 C8 C7 -159.61(17) . . . . ?
C11 C7 C8 C9 -87.64(19) . . . . ?
C6 C7 C8 C9 37.6(2) . . . . ?
C11 C7 C8 N2 153.30(15) . . . . ?
C6 C7 C8 N2 -81.5(2) . . . . ?
C1 O1 C9 C8 52.6(2) . . . . ?
N2 C8 C9 O1 60.5(2) . . . . ?
C7 C8 C9 O1 -62.4(2) . . . . ?
C17 N1 C10 C11 -1.0(2) . . . . ?
N1 C10 C11 C12 0.7(2) . . . . ?
N1 C10 C11 C7 -176.30(19) . . . . ?
C6 C7 C11 C10 -36.9(3) . . . . ?
C8 C7 C11 C10 86.2(2) . . . . ?
C6 C7 C11 C12 146.57(19) . . . . ?
C8 C7 C11 C12 -90.3(2) . . . . ?
C10 C11 C12 C13 179.7(2) . . . . ?
C7 C11 C12 C13 -3.2(4) . . . . ?
C10 C11 C12 C17 -0.2(2) . . . . ?
C7 C11 C12 C17 176.94(17) . . . . ?
C17 C12 C13 C14 0.4(3) . . . . ?
C11 C12 C13 C14 -179.5(2) . . . . ?
C12 C13 C14 C15 -0.1(3) . . . . ?
C13 C14 C15 C16 -0.6(3) . . . . ?
C14 C15 C16 C17 1.0(3) . . . . ?
C10 N1 C17 C16 -179.6(2) . . . . ?
C10 N1 C17 C12 0.8(2) . . . . ?
C15 C16 C17 N1 179.66(19) . . . . ?
C15 C16 C17 C12 -0.8(3) . . . . ?
C13 C12 C17 N1 179.74(17) . . . . ?
C11 C12 C17 N1 -0.3(2) . . . . ?
C13 C12 C17 C16 0.1(3) . . . . ?
C11 C12 C17 C16 179.99(18) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        29.12
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.051