# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_t

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H10 Br N O3'
_chemical_formula_weight         284.11

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   Pbca

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'
'-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                   12.936(3)
_cell_length_b                   12.022(2)
_cell_length_c                   14.578(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2267.1(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3067
_cell_measurement_theta_min      2.70
_cell_measurement_theta_max      23.66

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1136
_exptl_absorpt_coefficient_mu    3.617
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.6708
_exptl_absorpt_correction_T_max  0.7137
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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            12486
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_av_sigmaI/netI    0.1014
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.70
_diffrn_reflns_theta_max         25.99
_reflns_number_total             2209
_reflns_number_gt                1812
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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 F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0000P)²+0.0000P] where P=(Fo²+2Fc²)/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_number_reflns         2209
_refine_ls_number_parameters     147
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0346
_refine_ls_wR_factor_ref         0.1224
_refine_ls_wR_factor_gt          0.1023
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_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 1.09248(3) 0.76340(3) 1.01120(3) 0.0652(2) Uani 1 1 d . . .
C1 C 0.88350(18) 0.5826(2) 0.85789(18) 0.0378(6) Uani 1 1 d . . .
C2 C 0.96603(17) 0.6499(2) 0.8817(2) 0.0412(6) Uani 1 1 d . . .
H2 H 1.0098 0.6798 0.8374 0.049 Uiso 1 1 calc R . .
C3 C 0.98071(19) 0.6710(2) 0.9741(2) 0.0419(6) Uani 1 1 d . . .
C4 C 0.9175(2) 0.6270(2) 1.0407(2) 0.0436(6) Uani 1 1 d . . .
H4 H 0.9299 0.6431 1.1021 0.052 Uiso 1 1 calc R . .
C5 C 0.8353(2) 0.5587(2) 1.01671(19) 0.0447(7) Uani 1 1 d . . .
H5 H 0.7921 0.5279 1.0610 0.054 Uiso 1 1 calc R . .
C6 C 0.82011(18) 0.53823(19) 0.92514(18) 0.0372(6) Uani 1 1 d . . .
C7 C 0.75007(18) 0.4749(2) 0.7914(2) 0.0423(6) Uani 1 1 d . . .
C8 C 0.85018(19) 0.5386(2) 0.76677(19) 0.0414(7) Uani 1 1 d . . .
C9 C 0.6618(2) 0.4155(3) 0.9337(2) 0.0609(9) Uani 1 1 d . . .
H9A H 0.6140 0.4692 0.9578 0.091 Uiso 1 1 calc R . .
H9B H 0.6913 0.3736 0.9833 0.091 Uiso 1 1 calc R . .
H9C H 0.6261 0.3660 0.8929 0.091 Uiso 1 1 calc R . .
C10 C 0.9272(2) 0.4589(3) 0.7239(2) 0.0633(9) Uani 1 1 d . . .
H10A H 0.8984 0.4281 0.6688 0.095 Uiso 1 1 calc R . .
H10B H 0.9422 0.3999 0.7664 0.095 Uiso 1 1 calc R . .
H10C H 0.9898 0.4981 0.7096 0.095 Uiso 1 1 calc R . .
C11 C 0.7516(2) 0.6903(2) 0.7105(2) 0.0527(7) Uani 1 1 d . . .
H11 H 0.7403 0.7450 0.6665 0.063 Uiso 1 1 calc R . .
N1 N 0.74330(15) 0.47229(17) 0.88428(17) 0.0428(6) Uani 1 1 d . . .
O1 O 0.69218(17) 0.43045(17) 0.73732(14) 0.0565(6) Uani 1 1 d . . .
O2 O 0.83165(14) 0.62307(16) 0.69757(13) 0.0501(5) Uani 1 1 d . . .
O3 O 0.69279(18) 0.68697(18) 0.77336(18) 0.0675(6) 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 0.0598(3) 0.0657(3) 0.0702(4) -0.00799(16) -0.02414(17) -0.01165(14)
C1 0.0347(11) 0.0467(14) 0.0319(15) -0.0026(11) -0.0026(11) 0.0056(10)
C2 0.0348(12) 0.0490(14) 0.0397(17) 0.0010(12) -0.0004(11) 0.0007(10)
C3 0.0406(13) 0.0415(14) 0.0436(17) -0.0046(12) -0.0138(12) 0.0030(11)
C4 0.0509(14) 0.0514(16) 0.0284(15) -0.0058(13) -0.0087(12) 0.0095(12)
C5 0.0487(15) 0.0528(17) 0.0325(16) 0.0021(12) 0.0007(12) 0.0029(12)
C6 0.0375(11) 0.0404(13) 0.0337(16) 0.0031(10) -0.0037(11) 0.0025(10)
C7 0.0397(14) 0.0440(14) 0.0431(18) -0.0035(12) -0.0053(11) 0.0047(11)
C8 0.0393(14) 0.0539(16) 0.0310(15) -0.0057(12) -0.0009(11) 0.0054(11)
C9 0.0562(17) 0.069(2) 0.058(2) 0.0108(16) -0.0027(16) -0.0183(14)
C10 0.0511(16) 0.085(2) 0.054(2) -0.0286(18) -0.0005(15) 0.0189(16)
C11 0.0585(17) 0.0510(16) 0.0486(19) 0.0058(14) -0.0072(16) 0.0019(13)
N1 0.0434(11) 0.0436(12) 0.0416(16) 0.0037(10) -0.0040(10) -0.0051(9)
O1 0.0560(12) 0.0593(13) 0.0543(15) -0.0106(10) -0.0157(10) -0.0071(10)
O2 0.0509(10) 0.0676(12) 0.0318(12) 0.0034(9) 0.0017(9) -0.0008(9)
O3 0.0674(14) 0.0666(14) 0.0686(17) 0.0081(11) 0.0139(13) 0.0203(11)

_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 1.902(3) . ?
C1 C2 1.384(4) . ?
C1 C6 1.385(3) . ?
C1 C8 1.493(4) . ?
C2 C3 1.384(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.375(4) . ?
C4 C5 1.389(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.371(4) . ?
C5 H5 0.9300 . ?
C6 N1 1.404(3) . ?
C7 O1 1.212(3) . ?
C7 N1 1.357(4) . ?
C7 C8 1.547(4) . ?
C8 O2 1.451(4) . ?
C8 C10 1.517(4) . ?
C9 N1 1.448(3) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 O3 1.192(4) . ?
C11 O2 1.328(3) . ?
C11 H11 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
C2 C1 C6 120.3(2) . . ?
C2 C1 C8 130.7(3) . . ?
C6 C1 C8 108.8(2) . . ?
C3 C2 C1 117.2(3) . . ?
C3 C2 H2 121.4 . . ?
C1 C2 H2 121.4 . . ?
C4 C3 C2 122.4(2) . . ?
C4 C3 Br1 118.4(2) . . ?
C2 C3 Br1 119.2(2) . . ?
C3 C4 C5 120.4(3) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 117.4(3) . . ?
C6 C5 H5 121.3 . . ?
C4 C5 H5 121.3 . . ?
C5 C6 C1 122.4(2) . . ?
C5 C6 N1 128.0(2) . . ?
C1 C6 N1 109.6(2) . . ?
O1 C7 N1 126.8(3) . . ?
O1 C7 C8 125.8(3) . . ?
N1 C7 C8 107.3(2) . . ?
O2 C8 C1 114.7(2) . . ?
O2 C8 C10 105.3(2) . . ?
C1 C8 C10 113.6(2) . . ?
O2 C8 C7 111.7(2) . . ?
C1 C8 C7 102.1(2) . . ?
C10 C8 C7 109.4(2) . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O3 C11 O2 125.9(3) . . ?
O3 C11 H11 117.1 . . ?
O2 C11 H11 117.1 . . ?
C7 N1 C6 111.4(2) . . ?
C7 N1 C9 123.7(2) . . ?
C6 N1 C9 124.8(3) . . ?
C11 O2 C8 117.2(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
C6 C1 C2 C3 -0.7(4) . . . . ?
C8 C1 C2 C3 -175.9(3) . . . . ?
C1 C2 C3 C4 0.5(4) . . . . ?
C1 C2 C3 Br1 -179.75(18) . . . . ?
C2 C3 C4 C5 0.0(4) . . . . ?
Br1 C3 C4 C5 -179.7(2) . . . . ?
C3 C4 C5 C6 -0.4(4) . . . . ?
C4 C5 C6 C1 0.3(4) . . . . ?
C4 C5 C6 N1 179.8(2) . . . . ?
C2 C1 C6 C5 0.3(4) . . . . ?
C8 C1 C6 C5 176.4(2) . . . . ?
C2 C1 C6 N1 -179.3(2) . . . . ?
C8 C1 C6 N1 -3.1(3) . . . . ?
C2 C1 C8 O2 -56.4(3) . . . . ?
C6 C1 C8 O2 128.0(2) . . . . ?
C2 C1 C8 C10 64.8(4) . . . . ?
C6 C1 C8 C10 -110.8(3) . . . . ?
C2 C1 C8 C7 -177.4(3) . . . . ?
C6 C1 C8 C7 6.9(3) . . . . ?
O1 C7 C8 O2 52.2(3) . . . . ?
N1 C7 C8 O2 -131.6(2) . . . . ?
O1 C7 C8 C1 175.3(3) . . . . ?
N1 C7 C8 C1 -8.5(3) . . . . ?
O1 C7 C8 C10 -64.0(4) . . . . ?
N1 C7 C8 C10 112.1(3) . . . . ?
O1 C7 N1 C6 -176.6(3) . . . . ?
C8 C7 N1 C6 7.2(3) . . . . ?
O1 C7 N1 C9 -1.2(4) . . . . ?
C8 C7 N1 C9 -177.3(2) . . . . ?
C5 C6 N1 C7 177.7(2) . . . . ?
C1 C6 N1 C7 -2.8(3) . . . . ?
C5 C6 N1 C9 2.3(4) . . . . ?
C1 C6 N1 C9 -178.2(2) . . . . ?
O3 C11 O2 C8 -0.8(4) . . . . ?
C1 C8 O2 C11 -67.6(3) . . . . ?
C10 C8 O2 C11 166.7(2) . . . . ?
C7 C8 O2 C11 48.0(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.413
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.085
_database_code_depnum_ccdc_archive 'CCDC 937531'
