# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © 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_name        'Min Shi'
_publ_contact_author_email       mshi@mail.sioc.ac.cn
loop_
_publ_author_name
'Min Shi'
'Long Huang'

data_cd21140
_database_code_depnum_ccdc_archive 'CCDC 812598'
#TrackingRef 'cd21140.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H13 Br N2 O'
_chemical_formula_weight         329.19

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'
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                   8.5810(18)
_cell_length_b                   9.4511(19)
_cell_length_c                   18.265(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1481.3(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2556
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      27.58

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664
_exptl_absorpt_coefficient_mu    2.772
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5349
_exptl_absorpt_correction_T_max  0.7060
_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            8034
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_sigmaI/netI    0.0537
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.23
_diffrn_reflns_theta_max         26.00
_reflns_number_total             2911
_reflns_number_gt                2230
_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^)+(0.0634P)^2^+0.0452P] 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   0.002(14)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2911
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0407
_refine_ls_wR_factor_ref         0.1216
_refine_ls_wR_factor_gt          0.1105
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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 0.48884(5) 0.23722(6) 0.84134(3) 0.1040(2) Uani 1 1 d . . .
N1 N 0.9545(3) 0.5632(3) 0.58801(15) 0.0536(6) Uani 1 1 d . . .
O1 O 1.2010(4) 0.4095(3) 0.50438(15) 0.0819(7) Uani 1 1 d . . .
C1 C 0.6408(4) 0.2879(4) 0.7703(2) 0.0682(10) Uani 1 1 d . . .
C2 C 0.6787(5) 0.1980(4) 0.7157(2) 0.0753(10) Uani 1 1 d . . .
H2 H 0.6320 0.1094 0.7128 0.090 Uiso 1 1 calc R . .
N2 N 0.7142(5) 0.4411(4) 0.4492(2) 0.0853(10) Uani 1 1 d . . .
C3 C 0.7883(4) 0.2391(4) 0.6639(2) 0.0652(9) Uani 1 1 d . . .
H3 H 0.8158 0.1769 0.6266 0.078 Uiso 1 1 calc R . .
C4 C 0.8571(4) 0.3716(3) 0.66698(18) 0.0532(7) Uani 1 1 d . . .
C5 C 0.8141(5) 0.4583(4) 0.7233(2) 0.0666(9) Uani 1 1 d . . .
H5 H 0.8593 0.5476 0.7263 0.080 Uiso 1 1 calc R . .
C6 C 0.7064(5) 0.4194(4) 0.7758(2) 0.0739(10) Uani 1 1 d . . .
H6 H 0.6794 0.4805 0.8137 0.089 Uiso 1 1 calc R . .
C7 C 0.9733(4) 0.4136(3) 0.60910(17) 0.0531(7) Uani 1 1 d . . .
H7 H 0.9501 0.3569 0.5655 0.064 Uiso 1 1 calc R . .
C8 C 1.1423(4) 0.3857(4) 0.62864(19) 0.0596(8) Uani 1 1 d . . .
C9 C 1.2522(5) 0.3870(4) 0.5656(2) 0.0663(9) Uani 1 1 d . . .
C10 C 1.4207(5) 0.3583(6) 0.5768(3) 0.0971(15) Uani 1 1 d . . .
H10A H 1.4769 0.3809 0.5329 0.146 Uiso 1 1 calc R . .
H10B H 1.4352 0.2601 0.5884 0.146 Uiso 1 1 calc R . .
H10C H 1.4589 0.4154 0.6164 0.146 Uiso 1 1 calc R . .
C11 C 1.1892(5) 0.3579(5) 0.6955(2) 0.0850(12) Uani 1 1 d . . .
H11A H 1.2937 0.3383 0.7045 0.102 Uiso 1 1 calc R . .
H11B H 1.1180 0.3577 0.7339 0.102 Uiso 1 1 calc R . .
C12 C 1.0158(5) 0.6770(3) 0.6231(2) 0.0657(9) Uani 1 1 d . . .
H12 H 1.0887 0.6743 0.6607 0.079 Uiso 1 1 calc R . .
C13 C 0.9517(5) 0.7956(4) 0.5936(2) 0.0740(11) Uani 1 1 d . . .
H13 H 0.9742 0.8881 0.6073 0.089 Uiso 1 1 calc R . .
C14 C 0.8470(5) 0.7549(4) 0.5397(2) 0.0741(10) Uani 1 1 d . . .
H14 H 0.7864 0.8145 0.5109 0.089 Uiso 1 1 calc R . .
C15 C 0.8498(4) 0.6091(3) 0.53706(18) 0.0564(8) Uani 1 1 d . . .
C16 C 0.7743(5) 0.5157(4) 0.4888(2) 0.0661(10) 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 0.0858(3) 0.1483(5) 0.0779(3) 0.0353(3) 0.0032(2) -0.0232(3)
N1 0.0609(16) 0.0453(13) 0.0546(16) 0.0050(11) -0.0007(12) 0.0013(11)
O1 0.1001(19) 0.0787(16) 0.067(2) 0.0068(13) 0.0143(16) 0.0060(16)
C1 0.0594(18) 0.085(3) 0.060(2) 0.021(2) -0.0088(17) -0.0051(18)
C2 0.084(3) 0.070(2) 0.072(3) 0.015(2) -0.015(2) -0.0168(19)
N2 0.098(3) 0.085(2) 0.073(2) 0.000(2) -0.021(2) 0.017(2)
C3 0.076(2) 0.0628(19) 0.057(2) 0.0046(17) -0.0068(18) -0.0074(17)
C4 0.0609(18) 0.0509(16) 0.0478(18) 0.0029(16) -0.0119(16) 0.0028(14)
C5 0.082(2) 0.0562(19) 0.061(2) 0.0011(17) 0.005(2) -0.0033(18)
C6 0.084(3) 0.076(2) 0.061(2) 0.0008(19) 0.011(2) 0.004(2)
C7 0.068(2) 0.0427(15) 0.0485(17) 0.0006(12) -0.0065(15) 0.0033(14)
C8 0.068(2) 0.0525(17) 0.058(2) -0.0004(16) -0.0043(17) 0.0069(16)
C9 0.076(2) 0.0536(18) 0.069(2) -0.0009(18) 0.0043(19) 0.0002(17)
C10 0.070(3) 0.105(3) 0.116(4) -0.018(3) 0.009(3) -0.001(2)
C11 0.072(3) 0.109(3) 0.073(3) 0.010(2) -0.009(2) 0.017(2)
C12 0.072(2) 0.0544(18) 0.070(2) -0.0019(17) 0.004(2) -0.0090(18)
C13 0.091(3) 0.0468(19) 0.084(3) -0.0003(18) 0.024(2) -0.0036(17)
C14 0.090(3) 0.057(2) 0.075(3) 0.0168(19) 0.018(2) 0.017(2)
C15 0.066(2) 0.0531(17) 0.0498(19) 0.0062(16) 0.0053(16) 0.0066(15)
C16 0.076(2) 0.067(2) 0.055(2) 0.0134(18) -0.006(2) 0.0169(19)

_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 C1 1.901(4) . ?
N1 C12 1.358(4) . ?
N1 C15 1.364(4) . ?
N1 C7 1.474(4) . ?
O1 C9 1.221(4) . ?
C1 C2 1.350(6) . ?
C1 C6 1.368(6) . ?
C2 C3 1.390(5) . ?
C2 H2 0.9300 . ?
N2 C16 1.134(5) . ?
C3 C4 1.385(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.366(5) . ?
C4 C7 1.507(5) . ?
C5 C6 1.383(5) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.516(5) . ?
C7 H7 0.9800 . ?
C8 C11 1.312(5) . ?
C8 C9 1.488(5) . ?
C9 C10 1.485(6) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9300 . ?
C11 H11B 0.9300 . ?
C12 C13 1.359(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.388(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.379(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.406(6) . ?

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
C12 N1 C15 108.9(3) . . ?
C12 N1 C7 126.4(3) . . ?
C15 N1 C7 123.7(3) . . ?
C2 C1 C6 121.8(4) . . ?
C2 C1 Br1 120.7(3) . . ?
C6 C1 Br1 117.5(3) . . ?
C1 C2 C3 119.4(3) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C4 C3 C2 120.9(4) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C5 C4 C3 117.3(3) . . ?
C5 C4 C7 123.3(3) . . ?
C3 C4 C7 119.5(3) . . ?
C4 C5 C6 122.9(3) . . ?
C4 C5 H5 118.5 . . ?
C6 C5 H5 118.5 . . ?
C1 C6 C5 117.7(4) . . ?
C1 C6 H6 121.1 . . ?
C5 C6 H6 121.1 . . ?
N1 C7 C4 111.3(3) . . ?
N1 C7 C8 109.5(3) . . ?
C4 C7 C8 114.9(3) . . ?
N1 C7 H7 106.9 . . ?
C4 C7 H7 106.9 . . ?
C8 C7 H7 106.9 . . ?
C11 C8 C9 121.8(4) . . ?
C11 C8 C7 123.2(3) . . ?
C9 C8 C7 115.0(3) . . ?
O1 C9 C10 120.5(4) . . ?
O1 C9 C8 118.8(4) . . ?
C10 C9 C8 120.6(4) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 120.0 . . ?
C8 C11 H11B 120.0 . . ?
H11A C11 H11B 120.0 . . ?
N1 C12 C13 108.0(3) . . ?
N1 C12 H12 126.0 . . ?
C13 C12 H12 126.0 . . ?
C12 C13 C14 108.3(3) . . ?
C12 C13 H13 125.8 . . ?
C14 C13 H13 125.8 . . ?
C15 C14 C13 106.9(4) . . ?
C15 C14 H14 126.6 . . ?
C13 C14 H14 126.6 . . ?
N1 C15 C14 107.8(3) . . ?
N1 C15 C16 122.1(3) . . ?
C14 C15 C16 129.9(4) . . ?
N2 C16 C15 179.2(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
C6 C1 C2 C3 0.5(6) . . . . ?
Br1 C1 C2 C3 178.9(3) . . . . ?
C1 C2 C3 C4 -0.9(6) . . . . ?
C2 C3 C4 C5 0.7(5) . . . . ?
C2 C3 C4 C7 -178.9(3) . . . . ?
C3 C4 C5 C6 -0.2(5) . . . . ?
C7 C4 C5 C6 179.4(3) . . . . ?
C2 C1 C6 C5 0.0(6) . . . . ?
Br1 C1 C6 C5 -178.4(3) . . . . ?
C4 C5 C6 C1 -0.2(6) . . . . ?
C12 N1 C7 C4 83.7(4) . . . . ?
C15 N1 C7 C4 -84.4(4) . . . . ?
C12 N1 C7 C8 -44.5(4) . . . . ?
C15 N1 C7 C8 147.4(3) . . . . ?
C5 C4 C7 N1 -38.6(4) . . . . ?
C3 C4 C7 N1 141.0(3) . . . . ?
C5 C4 C7 C8 86.6(4) . . . . ?
C3 C4 C7 C8 -93.8(4) . . . . ?
N1 C7 C8 C11 111.3(4) . . . . ?
C4 C7 C8 C11 -14.9(5) . . . . ?
N1 C7 C8 C9 -70.8(4) . . . . ?
C4 C7 C8 C9 163.1(3) . . . . ?
C11 C8 C9 O1 177.9(4) . . . . ?
C7 C8 C9 O1 -0.1(5) . . . . ?
C11 C8 C9 C10 -0.8(6) . . . . ?
C7 C8 C9 C10 -178.8(4) . . . . ?
C15 N1 C12 C13 -0.9(4) . . . . ?
C7 N1 C12 C13 -170.5(3) . . . . ?
N1 C12 C13 C14 0.8(4) . . . . ?
C12 C13 C14 C15 -0.3(4) . . . . ?
C12 N1 C15 C14 0.8(4) . . . . ?
C7 N1 C15 C14 170.7(3) . . . . ?
C12 N1 C15 C16 176.0(3) . . . . ?
C7 N1 C15 C16 -14.1(5) . . . . ?
C13 C14 C15 N1 -0.3(4) . . . . ?
C13 C14 C15 C16 -175.0(4) . . . . ?
N1 C15 C16 N2 -116(28) . . . . ?
C14 C15 C16 N2 58(28) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.639
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.051