# Electronic Supplementary Material (ESI) for Chemical Communications
# 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
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  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_I
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C17 H12 Br N O'
_chemical_formula_sum            'C17 H12 Br N O'
_chemical_formula_iupac          ?
_chemical_formula_weight         326.19
_chemical_absolute_configuration ad

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_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                   5.1024(5)
_cell_length_b                   12.3099(12)
_cell_length_c                   22.118(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1389.2(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7466
_cell_measurement_theta_min      2.4757
_cell_measurement_theta_max      27.6568
_cell_measurement_temperature    173.(2)

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.120
_exptl_crystal_density_diffrn    1.560
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656

_exptl_absorpt_coefficient_mu    2.953
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.48
_exptl_absorpt_correction_T_max  0.72

_exptl_special_details           
;

A X-ray quality crystal was selected under ambient conditions
and covered with PARATONE oil
The crystal was mounted and centered in the X-ray beam by
using a video camera.The crystal evaluation and data
collection were performed on APEX-2 CCD diffractometer
with the detector to crystal distance of 5cm. 
The initial cell constants were obtained from three series of
OMEGA scans at different starting angles. Each series consisted
of 30 frames collected at intervals of 0.3 in a 10 range about
OMEGA with the exposure time of 10 seconds per frame. The 
obtained reflections were successfully indexed by an automated
indexing routine built to APEX2 program package. The final cell 
constants were calculated from a set of strong reflections from
the actual data collection.  

The data were collected using the full sphere routine by
collecting four sets of frames with 0.3 scans in \w with an
exposure time 10 sec per frame till resolution of 0.69 \%A. 
Data were truncated to the resolution with  statistically 
reasonable R~\s~.

;

_diffrn_ambient_temperature      173.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           ?
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            19879
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_sigmaI/netI    ?
_diffrn_reflns_theta_min         1.84
_diffrn_reflns_theta_max         28.73
_diffrn_reflns_theta_full        28.73
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29

_refine_special_details          
;
The systematic absences in the diffraction data were consistent for the
stated space group. The position of almost all non-hydrogen atoms
were found by direct methods. The remaining atoms were located in an 
alternating series of least-squares cycles on difference Fourier maps.
All non-hydrogen atoms were refined in full-matrix anisotropic approximation.
All hydrogen atoms were placed in the structure factor calculation at
idealized positions and were allowed to ride on the neighboring atoms with
relative isotropic displacement coefficients. 

All other expected hydrogen 
atoms were placed on a calculated positions and were refined in isotropic
approximation using "riding" model. The U~iso~(H) values have been set 
at 1.2  - 1.5  times the U~eq~ value of the carrier atom.

Final results were tested with CHECKCIF routine and all A-warnings (if any)
were addressed on the very top of this file.
;

_reflns_number_total             3580
_reflns_number_gt                3250
_reflns_threshold_expression     'I > 2\s(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0263
_refine_ls_R_factor_gt           0.0218
_refine_ls_wR_factor_gt          0.0503
_refine_ls_wR_factor_ref         0.0514
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_restrained_S_all      0.999
_refine_ls_number_reflns         3580
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
w=1/[\s^2^(Fo^2^)+(0.0253P)^2^]
where P=(Fo^2^+2Fc^2^)/3
;

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.278
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
Flack x determined using 1254 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.005(4)

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'

_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.30C (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.30C (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.64319(5) 0.04058(2) 0.38453(2) 0.03808(8) Uani d . . . 1 . .
C C1 0.6029(4) 0.35266(17) 0.31972(8) 0.0239(4) Uani d . . . 1 . .
C C2 0.6773(5) 0.43285(18) 0.27798(9) 0.0299(5) Uani d . . . 1 . .
H H2 0.5951 0.5021 0.2771 0.036 Uiso calc U . R 1 . .
C C3 0.8759(5) 0.4060(2) 0.23822(10) 0.0376(5) Uani d . . . 1 . .
H H3 0.9303 0.4581 0.2091 0.045 Uiso calc U . R 1 . .
C C4 0.9999(5) 0.3040(2) 0.23957(10) 0.0390(6) Uani d . . . 1 . .
H H4 1.1398 0.2897 0.2124 0.047 Uiso calc U . R 1 . .
C C5 0.9227(5) 0.2247(2) 0.27945(10) 0.0338(5) Uani d . . . 1 . .
H H5 1.0066 0.1558 0.2798 0.041 Uiso calc U . R 1 . .
C C6 0.7167(4) 0.24757(18) 0.31974(9) 0.0256(5) Uani d . . . 1 . .
C C7 0.5844(4) 0.18652(17) 0.36528(9) 0.0249(5) Uani d . . . 1 . .
C C8 0.4046(4) 0.25437(15) 0.39177(8) 0.0217(4) Uani d . . . 1 . .
C C9 0.2005(4) 0.25719(17) 0.43808(9) 0.0229(4) Uani d . . . 1 . .
C C10 0.0963(4) 0.37250(17) 0.43967(9) 0.0262(4) Uani d . . . 1 . .
H H10A 0.1371 0.4068 0.4791 0.031 Uiso calc U . R 1 . .
H H10B -0.0962 0.3726 0.4341 0.031 Uiso calc U . R 1 . .
C C11 0.2306(4) 0.43608(15) 0.38758(10) 0.0227(4) Uani d . . . 1 . .
H H11 0.0981 0.4516 0.3554 0.027 Uiso calc U . R 1 . .
C C12 0.3668(4) 0.54091(16) 0.40471(8) 0.0226(4) Uani d . . . 1 . .
C C13 0.5413(4) 0.54522(19) 0.45283(10) 0.0287(5) Uani d . . . 1 . .
H H13 0.5669 0.483 0.4775 0.034 Uiso calc U . R 1 . .
C C14 0.6776(5) 0.6395(2) 0.46491(11) 0.0381(6) Uani d . . . 1 . .
H H14 0.799 0.6413 0.4975 0.046 Uiso calc U . R 1 . .
C C15 0.6390(6) 0.73182(19) 0.42992(12) 0.0410(6) Uani d . . . 1 . .
H H15 0.7343 0.7964 0.4381 0.049 Uiso calc U . R 1 . .
C C16 0.4610(5) 0.72860(19) 0.38319(12) 0.0391(6) Uani d . . . 1 . .
H H16 0.4302 0.7918 0.3596 0.047 Uiso calc U . R 1 . .
C C17 0.3268(5) 0.63381(18) 0.37044(10) 0.0320(5) Uani d . . . 1 . .
H H17 0.2058 0.6323 0.3378 0.038 Uiso calc U . R 1 . .
N N1 0.4190(3) 0.35458(14) 0.36469(7) 0.0218(4) Uani d . . . 1 . .
O O1 0.1248(3) 0.18201(12) 0.46919(6) 0.0303(3) Uani d . . . 1 . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Br1 0.05404(15) 0.02108(10) 0.03912(13) 0.00377(11) 0.00356(13) -0.00344(10)
C1 0.0253(11) 0.0290(10) 0.0173(9) -0.0061(9) -0.0014(8) -0.0029(8)
C2 0.0346(13) 0.0324(11) 0.0226(10) -0.0095(9) 0.0025(9) -0.0005(8)
C3 0.0446(14) 0.0443(13) 0.0238(10) -0.0181(13) 0.0079(12) -0.0018(9)
C4 0.0371(13) 0.0537(16) 0.0261(12) -0.0115(12) 0.0111(11) -0.0145(12)
C5 0.0341(13) 0.0373(13) 0.0299(11) -0.0030(10) 0.0052(10) -0.0120(10)
C6 0.0281(11) 0.0286(11) 0.0201(10) -0.0045(9) -0.0010(8) -0.0071(8)
C7 0.0303(12) 0.0208(10) 0.0237(10) -0.0022(8) -0.0030(8) -0.0039(8)
C8 0.0231(10) 0.0204(9) 0.0215(9) -0.0058(8) -0.0032(8) 0.0022(7)
C9 0.0203(11) 0.0264(10) 0.0221(9) -0.0046(8) -0.0054(8) 0.0010(8)
C10 0.0232(11) 0.0284(11) 0.0271(11) -0.0002(9) 0.0031(9) 0.0045(9)
C11 0.0198(9) 0.0246(10) 0.0237(10) 0.0014(7) -0.0017(8) 0.0057(8)
C12 0.0223(9) 0.0228(9) 0.0227(8) 0.0045(11) 0.0036(8) 0.0019(8)
C13 0.0294(11) 0.0251(10) 0.0317(11) 0.0073(10) -0.0043(9) 0.0004(10)
C14 0.0351(14) 0.0334(12) 0.0460(14) -0.0009(11) -0.0086(12) -0.0091(10)
C15 0.0418(13) 0.0244(11) 0.0567(15) -0.0027(12) 0.0091(14) -0.0089(10)
C16 0.0463(14) 0.0228(11) 0.0483(14) 0.0010(10) 0.0097(13) 0.0089(11)
C17 0.0362(13) 0.0283(11) 0.0314(12) 0.0028(10) -0.0013(10) 0.0073(9)
N1 0.0234(9) 0.0224(9) 0.0195(8) -0.0029(7) 0.0011(7) 0.0014(6)
O1 0.0296(8) 0.0294(8) 0.0320(8) -0.0055(7) 0.0014(8) 0.0098(6)

_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C7 . 1.871(2) ?
C1 N1 . 1.367(3) ?
C1 C2 . 1.404(3) ?
C1 C6 . 1.418(3) ?
C2 C3 . 1.382(3) ?
C2 H2 . 0.95 ?
C3 C4 . 1.406(4) ?
C3 H3 . 0.95 ?
C4 C5 . 1.374(3) ?
C4 H4 . 0.95 ?
C5 C6 . 1.406(3) ?
C5 H5 . 0.95 ?
C6 C7 . 1.427(3) ?
C7 C8 . 1.372(3) ?
C8 N1 . 1.373(2) ?
C8 C9 . 1.461(3) ?
C9 O1 . 1.216(2) ?
C9 C10 . 1.516(3) ?
C10 C11 . 1.552(3) ?
C10 H10A . 0.99 ?
C10 H10B . 0.99 ?
C11 N1 . 1.479(3) ?
C11 C12 . 1.514(3) ?
C11 H11 . 1.0 ?
C12 C17 . 1.387(3) ?
C12 C13 . 1.389(3) ?
C13 C14 . 1.379(3) ?
C13 H13 . 0.95 ?
C14 C15 . 1.389(4) ?
C14 H14 . 0.95 ?
C15 C16 . 1.377(4) ?
C15 H15 . 0.95 ?
C16 C17 . 1.382(3) ?
C16 H16 . 0.95 ?
C17 H17 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 C1 C2 . . 130.7(2) ?
N1 C1 C6 . . 107.24(18) ?
C2 C1 C6 . . 122.1(2) ?
C3 C2 C1 . . 116.7(2) ?
C3 C2 H2 . . 121.7 ?
C1 C2 H2 . . 121.7 ?
C2 C3 C4 . . 122.0(2) ?
C2 C3 H3 . . 119.0 ?
C4 C3 H3 . . 119.0 ?
C5 C4 C3 . . 121.3(2) ?
C5 C4 H4 . . 119.4 ?
C3 C4 H4 . . 119.4 ?
C4 C5 C6 . . 118.6(2) ?
C4 C5 H5 . . 120.7 ?
C6 C5 H5 . . 120.7 ?
C5 C6 C1 . . 119.2(2) ?
C5 C6 C7 . . 134.1(2) ?
C1 C6 C7 . . 106.68(18) ?
C8 C7 C6 . . 107.29(19) ?
C8 C7 Br1 . . 126.49(16) ?
C6 C7 Br1 . . 126.21(16) ?
C7 C8 N1 . . 108.95(17) ?
C7 C8 C9 . . 142.21(19) ?
N1 C8 C9 . . 108.83(17) ?
O1 C9 C8 . . 127.2(2) ?
O1 C9 C10 . . 126.01(19) ?
C8 C9 C10 . . 106.76(16) ?
C9 C10 C11 . . 107.46(16) ?
C9 C10 H10A . . 110.2 ?
C11 C10 H10A . . 110.2 ?
C9 C10 H10B . . 110.2 ?
C11 C10 H10B . . 110.2 ?
H10A C10 H10B . . 108.5 ?
N1 C11 C12 . . 111.44(16) ?
N1 C11 C10 . . 101.48(15) ?
C12 C11 C10 . . 116.53(18) ?
N1 C11 H11 . . 109.0 ?
C12 C11 H11 . . 109.0 ?
C10 C11 H11 . . 109.0 ?
C17 C12 C13 . . 118.8(2) ?
C17 C12 C11 . . 119.91(19) ?
C13 C12 C11 . . 121.25(18) ?
C14 C13 C12 . . 120.3(2) ?
C14 C13 H13 . . 119.9 ?
C12 C13 H13 . . 119.9 ?
C13 C14 C15 . . 120.6(2) ?
C13 C14 H14 . . 119.7 ?
C15 C14 H14 . . 119.7 ?
C16 C15 C14 . . 119.2(2) ?
C16 C15 H15 . . 120.4 ?
C14 C15 H15 . . 120.4 ?
C15 C16 C17 . . 120.3(2) ?
C15 C16 H16 . . 119.9 ?
C17 C16 H16 . . 119.9 ?
C16 C17 C12 . . 120.8(2) ?
C16 C17 H17 . . 119.6 ?
C12 C17 H17 . . 119.6 ?
C1 N1 C8 . . 109.79(17) ?
C1 N1 C11 . . 134.96(17) ?
C8 N1 C11 . . 115.16(16) ?


_database_code_depnum_ccdc_archive 'CCDC 976167'