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


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#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication 
#  deposited with the CCDC, and may include chemical, crystal,   
#  experimental, refinement, atomic coordinates, 
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted. 
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#  fide research purposes only. It may contain copyright material 
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data_smd250_6c
_database_code_depnum_ccdc_archive 'CCDC 906681'
#TrackingRef '14765_web_deposit_cif_file_0_ConsigliaTedesco_1350550525.smd250_6csav.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H12 Br N O3'
_chemical_formula_sum            'C16 H12 Br N O3'
_chemical_formula_weight         346.18
_chemical_absolute_configuration ad

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   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

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

_cell_length_a                   9.801(3)
_cell_length_b                   10.969(3)
_cell_length_c                   14.070(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1512.6(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    9915
_cell_measurement_theta_min      1.4472
_cell_measurement_theta_max      27.6982


_exptl_crystal_description       prism
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.29
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.520
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696
_exptl_absorpt_coefficient_mu    2.726
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.2456
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      295(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18126
_diffrn_reflns_av_R_equivalents  0.0979
_diffrn_reflns_av_sigmaI/netI    0.0707
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.35
_diffrn_reflns_theta_max         28.06
_reflns_number_total             3466
_reflns_number_gt                2339
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_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^)+(0.1000P)^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     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.018(19)
_refine_ls_number_reflns         3466
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1224
_refine_ls_R_factor_gt           0.0789
_refine_ls_wR_factor_ref         0.1993
_refine_ls_wR_factor_gt          0.1777
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_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
Br1 Br 0.13762(9) 0.36060(8) 0.22125(5) 0.0861(4) Uani 1 1 d . . .
O1 O 0.4575(4) 0.3342(4) 0.5579(3) 0.0604(11) Uani 1 1 d . . .
H1 H 0.5153 0.3328 0.5158 0.091 Uiso 1 1 calc R . .
O2 O 0.4212(5) 0.0710(5) 0.5562(3) 0.0775(14) Uani 1 1 d . . .
O3 O 0.1156(5) 0.2465(5) 0.5898(3) 0.0718(13) Uani 1 1 d . . .
N1 N 0.2774(5) 0.3193(5) 0.6880(3) 0.0553(13) Uani 1 1 d . . .
H1A H 0.3603 0.3451 0.6883 0.066 Uiso 1 1 calc R . .
C1 C 0.1992(7) 0.2164(6) 0.2797(5) 0.0589(15) Uani 1 1 d . . .
C2 C 0.1827(7) 0.1079(7) 0.2341(5) 0.0708(19) Uani 1 1 d . . .
H2 H 0.1414 0.1057 0.1746 0.085 Uiso 1 1 calc R . .
C3 C 0.2271(10) 0.0003(8) 0.2761(6) 0.090(2) Uani 1 1 d . . .
H3 H 0.2162 -0.0736 0.2445 0.108 Uiso 1 1 calc R . .
C4 C 0.2882(9) 0.0032(7) 0.3655(5) 0.077(2) Uani 1 1 d . . .
H4 H 0.3200 -0.0677 0.3940 0.093 Uiso 1 1 calc R . .
C5 C 0.2999(6) 0.1132(6) 0.4100(4) 0.0554(15) Uani 1 1 d . . .
C6 C 0.2573(6) 0.2205(5) 0.3703(4) 0.0479(13) Uani 1 1 d . . .
C7 C 0.2797(6) 0.3297(5) 0.4310(4) 0.0491(14) Uani 1 1 d . . .
H7A H 0.1946 0.3724 0.4422 0.059 Uiso 1 1 calc R . .
H7B H 0.3439 0.3853 0.4014 0.059 Uiso 1 1 calc R . .
C8 C 0.3386(6) 0.2776(6) 0.5256(4) 0.0496(14) Uani 1 1 d . . .
C9 C 0.3622(6) 0.1402(6) 0.5049(4) 0.0564(14) Uani 1 1 d . . .
C10 C 0.2326(6) 0.2804(6) 0.6046(4) 0.0487(14) Uani 1 1 d . . .
C11 C 0.2086(6) 0.3250(6) 0.7779(4) 0.0558(14) Uani 1 1 d . . .
C12 C 0.2872(7) 0.3367(7) 0.8588(4) 0.0654(19) Uani 1 1 d . . .
H12 H 0.3817 0.3410 0.8538 0.078 Uiso 1 1 calc R . .
C13 C 0.2267(8) 0.3422(8) 0.9462(4) 0.072(2) Uani 1 1 d . . .
H13 H 0.2807 0.3489 1.0003 0.086 Uiso 1 1 calc R . .
C14 C 0.0900(9) 0.3379(9) 0.9552(5) 0.086(2) Uani 1 1 d . . .
H14 H 0.0495 0.3425 1.0149 0.103 Uiso 1 1 calc R . .
C15 C 0.0124(9) 0.3268(15) 0.8759(5) 0.125(5) Uani 1 1 d . . .
H15 H -0.0820 0.3233 0.8819 0.150 Uiso 1 1 calc R . .
C16 C 0.0710(8) 0.3206(11) 0.7849(5) 0.104(3) Uani 1 1 d . . .
H16 H 0.0167 0.3138 0.7310 0.125 Uiso 1 1 calc R . .

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 0.1276(7) 0.0868(5) 0.0439(3) 0.0001(3) -0.0191(4) 0.0186(5)
O1 0.058(2) 0.086(3) 0.038(2) -0.008(2) -0.0016(16) -0.008(2)
O2 0.100(3) 0.078(3) 0.054(3) 0.014(3) -0.003(3) 0.024(3)
O3 0.064(3) 0.111(4) 0.040(2) -0.011(2) -0.0001(19) -0.009(3)
N1 0.060(3) 0.070(4) 0.035(2) -0.003(2) 0.003(2) -0.001(2)
C1 0.076(4) 0.061(4) 0.040(3) -0.012(3) -0.001(3) 0.000(3)
C2 0.082(4) 0.080(5) 0.050(4) -0.019(3) -0.013(3) -0.010(4)
C3 0.133(7) 0.066(5) 0.070(5) -0.018(4) -0.015(5) -0.009(5)
C4 0.118(6) 0.051(4) 0.062(4) -0.009(3) -0.004(4) 0.008(4)
C5 0.066(4) 0.054(4) 0.047(3) 0.000(3) 0.006(3) 0.001(3)
C6 0.055(3) 0.050(3) 0.039(3) -0.007(2) 0.007(2) -0.002(3)
C7 0.065(4) 0.054(4) 0.029(2) -0.002(2) -0.001(2) 0.002(3)
C8 0.058(4) 0.059(3) 0.032(2) 0.001(2) -0.002(2) 0.002(3)
C9 0.071(4) 0.057(3) 0.042(3) 0.009(3) 0.004(3) 0.007(4)
C10 0.051(4) 0.062(4) 0.033(3) -0.003(3) 0.004(2) -0.001(3)
C11 0.070(4) 0.066(4) 0.032(3) -0.008(3) -0.001(3) 0.004(3)
C12 0.069(4) 0.086(5) 0.041(3) -0.005(3) -0.003(3) -0.005(4)
C13 0.099(6) 0.086(5) 0.031(3) -0.002(3) -0.008(3) 0.007(4)
C14 0.106(6) 0.119(7) 0.032(3) -0.008(4) 0.006(3) 0.001(5)
C15 0.075(5) 0.253(14) 0.047(4) -0.014(7) 0.018(4) -0.001(6)
C16 0.068(4) 0.207(11) 0.037(3) -0.001(5) 0.000(3) 0.011(5)

_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 1.882(7) . ?
O1 C8 1.396(7) . ?
O1 H1 0.8200 . ?
O2 C9 1.196(7) . ?
O3 C10 1.223(7) . ?
N1 C10 1.323(7) . ?
N1 C11 1.435(8) . ?
N1 H1A 0.8600 . ?
C1 C2 1.362(9) . ?
C1 C6 1.397(9) . ?
C2 C3 1.390(11) . ?
C2 H2 0.9300 . ?
C3 C4 1.393(11) . ?
C3 H3 0.9300 . ?
C4 C5 1.364(10) . ?
C4 H4 0.9300 . ?
C5 C6 1.368(9) . ?
C5 C9 1.498(8) . ?
C6 C7 1.487(8) . ?
C7 C8 1.560(7) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C10 1.522(8) . ?
C8 C9 1.553(9) . ?
C11 C16 1.353(10) . ?
C11 C12 1.381(8) . ?
C12 C13 1.366(9) . ?
C12 H12 0.9300 . ?
C13 C14 1.346(11) . ?
C13 H13 0.9300 . ?
C14 C15 1.356(11) . ?
C14 H14 0.9300 . ?
C15 C16 1.405(11) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?

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
C8 O1 H1 109.5 . . ?
C10 N1 C11 129.7(5) . . ?
C10 N1 H1A 115.1 . . ?
C11 N1 H1A 115.1 . . ?
C2 C1 C6 120.4(7) . . ?
C2 C1 Br1 119.4(5) . . ?
C6 C1 Br1 120.1(5) . . ?
C1 C2 C3 120.4(6) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C2 C3 C4 119.9(7) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 118.1(7) . . ?
C5 C4 H4 120.9 . . ?
C3 C4 H4 120.9 . . ?
C6 C5 C4 123.2(6) . . ?
C6 C5 C9 108.6(5) . . ?
C4 C5 C9 128.2(6) . . ?
C5 C6 C1 118.0(6) . . ?
C5 C6 C7 114.4(5) . . ?
C1 C6 C7 127.6(6) . . ?
C6 C7 C8 104.5(5) . . ?
C6 C7 H7A 110.9 . . ?
C8 C7 H7A 110.9 . . ?
C6 C7 H7B 110.9 . . ?
C8 C7 H7B 110.9 . . ?
H7A C7 H7B 108.9 . . ?
O1 C8 C10 108.9(4) . . ?
O1 C8 C9 111.6(5) . . ?
C10 C8 C9 105.0(5) . . ?
O1 C8 C7 115.1(5) . . ?
C10 C8 C7 111.3(5) . . ?
C9 C8 C7 104.5(4) . . ?
O2 C9 C5 127.6(6) . . ?
O2 C9 C8 125.1(6) . . ?
C5 C9 C8 107.4(5) . . ?
O3 C10 N1 124.1(5) . . ?
O3 C10 C8 120.6(5) . . ?
N1 C10 C8 115.3(5) . . ?
C16 C11 C12 120.0(6) . . ?
C16 C11 N1 122.1(6) . . ?
C12 C11 N1 117.9(5) . . ?
C13 C12 C11 120.2(6) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C14 C13 C12 121.1(6) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C13 C14 C15 118.9(7) . . ?
C13 C14 H14 120.6 . . ?
C15 C14 H14 120.6 . . ?
C14 C15 C16 121.7(8) . . ?
C14 C15 H15 119.2 . . ?
C16 C15 H15 119.2 . . ?
C11 C16 C15 118.2(7) . . ?
C11 C16 H16 120.9 . . ?
C15 C16 H16 120.9 . . ?

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 -1.9(11) . . . . ?
Br1 C1 C2 C3 -179.9(6) . . . . ?
C1 C2 C3 C4 0.4(12) . . . . ?
C2 C3 C4 C5 1.2(13) . . . . ?
C3 C4 C5 C6 -1.4(12) . . . . ?
C3 C4 C5 C9 -179.3(7) . . . . ?
C4 C5 C6 C1 -0.1(10) . . . . ?
C9 C5 C6 C1 178.2(5) . . . . ?
C4 C5 C6 C7 180.0(7) . . . . ?
C9 C5 C6 C7 -1.7(7) . . . . ?
C2 C1 C6 C5 1.7(9) . . . . ?
Br1 C1 C6 C5 179.7(4) . . . . ?
C2 C1 C6 C7 -178.4(6) . . . . ?
Br1 C1 C6 C7 -0.4(9) . . . . ?
C5 C6 C7 C8 -3.6(7) . . . . ?
C1 C6 C7 C8 176.4(6) . . . . ?
C6 C7 C8 O1 129.9(5) . . . . ?
C6 C7 C8 C10 -105.7(5) . . . . ?
C6 C7 C8 C9 7.1(6) . . . . ?
C6 C5 C9 O2 -172.8(6) . . . . ?
C4 C5 C9 O2 5.5(11) . . . . ?
C6 C5 C9 C8 6.4(6) . . . . ?
C4 C5 C9 C8 -175.4(7) . . . . ?
O1 C8 C9 O2 45.9(8) . . . . ?
C10 C8 C9 O2 -71.8(7) . . . . ?
C7 C8 C9 O2 170.9(6) . . . . ?
O1 C8 C9 C5 -133.3(5) . . . . ?
C10 C8 C9 C5 109.0(5) . . . . ?
C7 C8 C9 C5 -8.3(6) . . . . ?
C11 N1 C10 O3 3.9(11) . . . . ?
C11 N1 C10 C8 -175.0(6) . . . . ?
O1 C8 C10 O3 172.9(6) . . . . ?
C9 C8 C10 O3 -67.4(7) . . . . ?
C7 C8 C10 O3 45.0(8) . . . . ?
O1 C8 C10 N1 -8.1(7) . . . . ?
C9 C8 C10 N1 111.5(6) . . . . ?
C7 C8 C10 N1 -136.0(6) . . . . ?
C10 N1 C11 C16 -18.7(12) . . . . ?
C10 N1 C11 C12 162.2(7) . . . . ?
C16 C11 C12 C13 1.0(13) . . . . ?
N1 C11 C12 C13 -179.8(7) . . . . ?
C11 C12 C13 C14 -0.9(14) . . . . ?
C12 C13 C14 C15 0.7(18) . . . . ?
C13 C14 C15 C16 0(2) . . . . ?
C12 C11 C16 C15 -0.8(16) . . . . ?
N1 C11 C16 C15 -180.0(10) . . . . ?
C14 C15 C16 C11 1(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.962
_diffrn_reflns_theta_full        28.06
_diffrn_measured_fraction_theta_full 0.962
_refine_diff_density_max         0.851
_refine_diff_density_min         -0.927
_refine_diff_density_rms         0.090