# Electronic Supplementary Material (ESI) for Organic & Biomolecular 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_b

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H16 Br N O2'
_chemical_formula_weight         370.24

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   P212121
_chemical_absolute_configuration ad

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                   17.158(3)
_cell_length_b                   6.0010(12)
_cell_length_c                   15.681(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1614.6(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      9
_cell_measurement_theta_max      13

_exptl_crystal_description       rod
_exptl_crystal_colour            'pale green'
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.523
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752
_exptl_absorpt_coefficient_mu    2.555
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.6290
_exptl_absorpt_correction_T_max  0.7842
_exptl_absorpt_process_details   ?

_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  'Nonius CAD4'
_diffrn_measurement_method       ω/2θ
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2h
_diffrn_standards_decay_%        1
_diffrn_reflns_number            3363
_diffrn_reflns_av_R_equivalents  0.0824
_diffrn_reflns_av_sigmaI/netI    0.1359
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.76
_diffrn_reflns_theta_max         25.37
_reflns_number_total             2962
_reflns_number_gt                1597
_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 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)+(0.0430P)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    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   0.00(2)
_refine_ls_number_reflns         2962
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1486
_refine_ls_R_factor_gt           0.0643
_refine_ls_wR_factor_ref         0.1261
_refine_ls_wR_factor_gt          0.1009
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_refine_ls_shift/su_max          0.000
_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
Br Br 0.45436(5) 0.95874(15) 0.30840(6) 0.0684(3) Uani 1 1 d . . .
N N 0.2015(3) 0.1763(10) 0.2061(4) 0.0441(17) Uani 1 1 d . . .
C1 C 0.3143(4) 0.2060(11) 0.1265(4) 0.0319(18) Uani 1 1 d . . .
H1A H 0.3523 0.1290 0.1627 0.038 Uiso 1 1 calc R . .
O1 O 0.1549(3) -0.1614(10) 0.1594(4) 0.071(2) Uani 1 1 d . . .
O2 O 0.3455(3) 0.5381(10) 0.0488(3) 0.0531(15) Uani 1 1 d . . .
C2 C 0.2607(4) 0.3429(11) 0.1836(5) 0.0385(19) Uani 1 1 d . . .
H2A H 0.2361 0.4598 0.1492 0.046 Uiso 1 1 calc R . .
C3 C 0.2956(4) 0.4481(14) 0.2626(4) 0.0344(18) Uani 1 1 d . . .
C4 C 0.3493(4) 0.6217(11) 0.2537(5) 0.0352(19) Uani 1 1 d . . .
H4A H 0.3633 0.6704 0.1995 0.042 Uiso 1 1 calc R . .
C5 C 0.3815(4) 0.7207(12) 0.3239(5) 0.041(2) Uani 1 1 d . . .
C6 C 0.3631(5) 0.6503(15) 0.4050(6) 0.050(2) Uani 1 1 d . . .
H6A H 0.3864 0.7148 0.4526 0.060 Uiso 1 1 calc R . .
C7 C 0.3096(4) 0.4827(15) 0.4136(5) 0.051(2) Uani 1 1 d . . .
H7A H 0.2962 0.4368 0.4683 0.062 Uiso 1 1 calc R . .
C8 C 0.2741(4) 0.3770(13) 0.3443(5) 0.039(2) Uani 1 1 d . . .
C9 C 0.2160(4) 0.1958(15) 0.3575(5) 0.053(2) Uani 1 1 d . . .
H9A H 0.1882 0.2203 0.4105 0.063 Uiso 1 1 calc R . .
H9B H 0.2425 0.0533 0.3612 0.063 Uiso 1 1 calc R . .
C10 C 0.1592(4) 0.1922(14) 0.2843(5) 0.053(2) Uani 1 1 d . . .
H10A H 0.1243 0.0658 0.2900 0.064 Uiso 1 1 calc R . .
H10B H 0.1281 0.3272 0.2847 0.064 Uiso 1 1 calc R . .
C11 C 0.1993(4) -0.0035(15) 0.1534(5) 0.047(2) Uani 1 1 d . . .
C12 C 0.2610(4) 0.0324(14) 0.0866(4) 0.045(2) Uani 1 1 d . . .
H12A H 0.2384 0.0870 0.0340 0.055 Uiso 1 1 calc R . .
H12B H 0.2891 -0.1046 0.0750 0.055 Uiso 1 1 calc R . .
C13 C 0.3585(4) 0.3398(14) 0.0601(5) 0.036(2) Uani 1 1 d . . .
C14 C 0.4163(4) 0.2207(13) 0.0039(5) 0.0371(19) Uani 1 1 d . . .
C15 C 0.4466(4) 0.0118(12) 0.0217(5) 0.049(2) Uani 1 1 d . . .
H15A H 0.4311 -0.0640 0.0706 0.059 Uiso 1 1 calc R . .
C16 C 0.5000(4) -0.0839(14) -0.0331(6) 0.057(3) Uani 1 1 d . . .
H16A H 0.5199 -0.2243 -0.0209 0.068 Uiso 1 1 calc R . .
C17 C 0.5241(4) 0.0257(18) -0.1059(6) 0.065(3) Uani 1 1 d . . .
H17A H 0.5595 -0.0405 -0.1430 0.078 Uiso 1 1 calc R . .
C18 C 0.4951(5) 0.2326(18) -0.1224(6) 0.071(3) Uani 1 1 d . . .
H18A H 0.5122 0.3108 -0.1700 0.085 Uiso 1 1 calc R . .
C19 C 0.4405(4) 0.3268(13) -0.0689(5) 0.053(2) Uani 1 1 d . . .
H19A H 0.4197 0.4654 -0.0825 0.063 Uiso 1 1 calc R . .


_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
Br C5 1.914(7) . ?
N C11 1.359(9) . ?
N C10 1.429(9) . ?
N C2 1.468(8) . ?
C1 C13 1.518(10) . ?
C1 C12 1.520(9) . ?
C1 C2 1.524(9) . ?
C1 H1A 0.9800 . ?
O1 C11 1.220(9) . ?
O2 C13 1.224(8) . ?
C2 C3 1.513(9) . ?
C2 H2A 0.9800 . ?
C3 C4 1.398(9) . ?
C3 C8 1.401(9) . ?
C4 C5 1.368(9) . ?
C4 H4A 0.9300 . ?
C5 C6 1.376(10) . ?
C6 C7 1.368(10) . ?
C6 H6A 0.9300 . ?
C7 C8 1.398(10) . ?
C7 H7A 0.9300 . ?
C8 C9 1.490(10) . ?
C9 C10 1.505(10) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.504(9) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.505(10) . ?
C14 C19 1.373(10) . ?
C14 C15 1.386(10) . ?
C15 C16 1.381(10) . ?
C15 H15A 0.9300 . ?
C16 C17 1.380(10) . ?
C16 H16A 0.9300 . ?
C17 C18 1.363(11) . ?
C17 H17A 0.9300 . ?
C18 C19 1.378(10) . ?
C18 H18A 0.9300 . ?
C19 H19A 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
C11 N C10 124.1(6) . . ?
C11 N C2 114.5(6) . . ?
C10 N C2 120.8(6) . . ?
C13 C1 C12 112.4(6) . . ?
C13 C1 C2 114.8(6) . . ?
C12 C1 C2 104.4(5) . . ?
C13 C1 H1A 108.3 . . ?
C12 C1 H1A 108.3 . . ?
C2 C1 H1A 108.3 . . ?
N C2 C3 111.2(6) . . ?
N C2 C1 101.0(5) . . ?
C3 C2 C1 117.8(5) . . ?
N C2 H2A 108.8 . . ?
C3 C2 H2A 108.8 . . ?
C1 C2 H2A 108.8 . . ?
C4 C3 C8 119.4(7) . . ?
C4 C3 C2 119.4(7) . . ?
C8 C3 C2 121.2(7) . . ?
C5 C4 C3 120.6(7) . . ?
C5 C4 H4A 119.7 . . ?
C3 C4 H4A 119.7 . . ?
C4 C5 C6 121.2(7) . . ?
C4 C5 Br 119.0(6) . . ?
C6 C5 Br 119.7(6) . . ?
C7 C6 C5 118.0(8) . . ?
C7 C6 H6A 121.0 . . ?
C5 C6 H6A 121.0 . . ?
C6 C7 C8 123.3(8) . . ?
C6 C7 H7A 118.3 . . ?
C8 C7 H7A 118.3 . . ?
C7 C8 C3 117.3(7) . . ?
C7 C8 C9 121.0(8) . . ?
C3 C8 C9 121.7(7) . . ?
C8 C9 C10 109.8(6) . . ?
C8 C9 H9A 109.7 . . ?
C10 C9 H9A 109.7 . . ?
C8 C9 H9B 109.7 . . ?
C10 C9 H9B 109.7 . . ?
H9A C9 H9B 108.2 . . ?
N C10 C9 109.0(6) . . ?
N C10 H10A 109.9 . . ?
C9 C10 H10A 109.9 . . ?
N C10 H10B 109.9 . . ?
C9 C10 H10B 109.9 . . ?
H10A C10 H10B 108.3 . . ?
O1 C11 N 125.9(7) . . ?
O1 C11 C12 127.2(8) . . ?
N C11 C12 106.9(7) . . ?
C11 C12 C1 103.6(6) . . ?
C11 C12 H12A 111.0 . . ?
C1 C12 H12A 111.0 . . ?
C11 C12 H12B 111.0 . . ?
C1 C12 H12B 111.0 . . ?
H12A C12 H12B 109.0 . . ?
O2 C13 C14 119.9(7) . . ?
O2 C13 C1 121.4(7) . . ?
C14 C13 C1 118.6(7) . . ?
C19 C14 C15 118.2(7) . . ?
C19 C14 C13 117.8(7) . . ?
C15 C14 C13 124.0(7) . . ?
C16 C15 C14 120.0(7) . . ?
C16 C15 H15A 120.0 . . ?
C14 C15 H15A 120.0 . . ?
C17 C16 C15 121.1(8) . . ?
C17 C16 H16A 119.5 . . ?
C15 C16 H16A 119.5 . . ?
C18 C17 C16 118.8(8) . . ?
C18 C17 H17A 120.6 . . ?
C16 C17 H17A 120.6 . . ?
C17 C18 C19 120.5(9) . . ?
C17 C18 H18A 119.8 . . ?
C19 C18 H18A 119.8 . . ?
C14 C19 C18 121.5(8) . . ?
C14 C19 H19A 119.3 . . ?
C18 C19 H19A 119.3 . . ?

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
C11 N C2 C3 -144.3(6) . . . . ?
C10 N C2 C3 26.9(9) . . . . ?
C11 N C2 C1 -18.4(8) . . . . ?
C10 N C2 C1 152.7(6) . . . . ?
C13 C1 C2 N 152.5(6) . . . . ?
C12 C1 C2 N 29.0(7) . . . . ?
C13 C1 C2 C3 -86.2(8) . . . . ?
C12 C1 C2 C3 150.3(6) . . . . ?
N C2 C3 C4 -175.7(6) . . . . ?
C1 C2 C3 C4 68.4(9) . . . . ?
N C2 C3 C8 3.3(9) . . . . ?
C1 C2 C3 C8 -112.6(8) . . . . ?
C8 C3 C4 C5 0.7(10) . . . . ?
C2 C3 C4 C5 179.7(6) . . . . ?
C3 C4 C5 C6 1.1(10) . . . . ?
C3 C4 C5 Br -179.7(5) . . . . ?
C4 C5 C6 C7 -2.1(11) . . . . ?
Br C5 C6 C7 178.7(5) . . . . ?
C5 C6 C7 C8 1.3(11) . . . . ?
C6 C7 C8 C3 0.3(11) . . . . ?
C6 C7 C8 C9 -179.8(7) . . . . ?
C4 C3 C8 C7 -1.4(10) . . . . ?
C2 C3 C8 C7 179.7(6) . . . . ?
C4 C3 C8 C9 178.8(7) . . . . ?
C2 C3 C8 C9 -0.2(11) . . . . ?
C7 C8 C9 C10 151.2(7) . . . . ?
C3 C8 C9 C10 -29.0(10) . . . . ?
C11 N C10 C9 113.2(8) . . . . ?
C2 N C10 C9 -57.0(9) . . . . ?
C8 C9 C10 N 54.2(9) . . . . ?
C10 N C11 O1 9.6(12) . . . . ?
C2 N C11 O1 -179.5(7) . . . . ?
C10 N C11 C12 -171.2(6) . . . . ?
C2 N C11 C12 -0.4(8) . . . . ?
O1 C11 C12 C1 -161.6(7) . . . . ?
N C11 C12 C1 19.2(8) . . . . ?
C13 C1 C12 C11 -155.1(6) . . . . ?
C2 C1 C12 C11 -30.1(7) . . . . ?
C12 C1 C13 O2 112.2(8) . . . . ?
C2 C1 C13 O2 -6.9(10) . . . . ?
C12 C1 C13 C14 -64.2(8) . . . . ?
C2 C1 C13 C14 176.7(6) . . . . ?
O2 C13 C14 C19 -13.1(11) . . . . ?
C1 C13 C14 C19 163.5(7) . . . . ?
O2 C13 C14 C15 166.5(7) . . . . ?
C1 C13 C14 C15 -17.0(10) . . . . ?
C19 C14 C15 C16 0.2(11) . . . . ?
C13 C14 C15 C16 -179.4(7) . . . . ?
C14 C15 C16 C17 0.2(11) . . . . ?
C15 C16 C17 C18 0.9(12) . . . . ?
C16 C17 C18 C19 -2.3(13) . . . . ?
C15 C14 C19 C18 -1.7(12) . . . . ?
C13 C14 C19 C18 177.9(7) . . . . ?
C17 C18 C19 C14 2.8(13) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.37
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.074
_database_code_depnum_ccdc_archive 'CCDC 1029009'
