# 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.
# 
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#  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.
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data_y

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H18 Br N O2'
_chemical_formula_sum            'C18 H18 Br N O2'
_chemical_formula_weight         360.23

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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   17.4725(10)
_cell_length_b                   8.0638(4)
_cell_length_c                   24.9462(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.2240(10)
_cell_angle_gamma                90.00
_cell_volume                     3318.8(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    4217
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      22.17

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      1.442
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1472
_exptl_absorpt_coefficient_mu    2.484
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      273(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            20430
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_av_sigmaI/netI    0.0450
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.73
_diffrn_reflns_theta_max         26.03
_reflns_number_total             6538
_reflns_number_gt                4809
_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)+(0.0551P)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         6519
_refine_ls_number_parameters     401
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0642
_refine_ls_R_factor_gt           0.0409
_refine_ls_wR_factor_ref         0.0994
_refine_ls_wR_factor_gt          0.0903
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_restrained_S_all      0.989
_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
C1 C 0.34075(18) 0.5971(4) 0.09682(13) 0.0349(7) Uani 1 1 d . . .
C2 C 0.27390(19) 0.5313(4) 0.05669(13) 0.0415(8) Uani 1 1 d . . .
H2 H 0.2782 0.4833 0.0239 0.050 Uiso 1 1 calc R . .
C3 C 0.19947(19) 0.5373(4) 0.06564(14) 0.0444(8) Uani 1 1 d . . .
H3 H 0.1538 0.4940 0.0383 0.053 Uiso 1 1 calc R . .
C4 C 0.19221(18) 0.6066(4) 0.11455(13) 0.0387(8) Uani 1 1 d . . .
C5 C 0.2608(2) 0.6729(5) 0.15379(14) 0.0489(9) Uani 1 1 d . . .
H5 H 0.2568 0.7226 0.1864 0.059 Uiso 1 1 calc R . .
C6 C 0.3356(2) 0.6670(5) 0.14559(14) 0.0463(8) Uani 1 1 d . . .
H6 H 0.3815 0.7099 0.1728 0.056 Uiso 1 1 calc R . .
C7 C 0.1540(3) 0.3945(6) 0.21926(19) 0.0872(15) Uani 1 1 d . . .
H7A H 0.1646 0.5112 0.2190 0.131 Uiso 1 1 calc R . .
H7B H 0.2040 0.3344 0.2276 0.131 Uiso 1 1 calc R . .
H7C H 0.1296 0.3707 0.2477 0.131 Uiso 1 1 calc R . .
C8 C 0.0708(3) 0.1746(5) 0.1588(2) 0.0933(16) Uani 1 1 d . . .
H8A H 0.0434 0.1541 0.1858 0.140 Uiso 1 1 calc R . .
H8B H 0.1158 0.1001 0.1658 0.140 Uiso 1 1 calc R . .
H8C H 0.0338 0.1574 0.1211 0.140 Uiso 1 1 calc R . .
C9 C 0.0708(2) 0.4490(4) 0.11991(15) 0.0472(9) Uani 1 1 d . . .
C10 C 0.11003(19) 0.6200(4) 0.12339(14) 0.0439(8) Uani 1 1 d . . .
H10 H 0.1183 0.6662 0.1612 0.053 Uiso 1 1 calc R . .
C11 C 0.0527(2) 0.7330(4) 0.07953(16) 0.0490(9) Uani 1 1 d . . .
H11A H 0.0823 0.8301 0.0744 0.059 Uiso 1 1 calc R . .
H11B H 0.0332 0.6751 0.0435 0.059 Uiso 1 1 calc R . .
C12 C -0.0191(2) 0.7881(4) 0.09605(17) 0.0499(9) Uani 1 1 d . . .
C13 C -0.08690(19) 0.8713(4) 0.05305(16) 0.0456(9) Uani 1 1 d . . .
C14 C -0.1040(2) 0.8480(5) -0.00424(17) 0.0563(10) Uani 1 1 d . . .
H14 H -0.0703 0.7814 -0.0172 0.068 Uiso 1 1 calc R . .
C15 C -0.1718(2) 0.9237(5) -0.04330(19) 0.0681(11) Uani 1 1 d . . .
H15 H -0.1840 0.9044 -0.0820 0.082 Uiso 1 1 calc R . .
C16 C -0.2199(2) 1.0261(5) -0.0245(2) 0.0711(12) Uani 1 1 d . . .
H16 H -0.2653 1.0751 -0.0503 0.085 Uiso 1 1 calc R . .
C17 C -0.2017(2) 1.0563(5) 0.0318(2) 0.0731(13) Uani 1 1 d . . .
H17 H -0.2330 1.1312 0.0439 0.088 Uiso 1 1 calc R . .
C18 C -0.1372(2) 0.9775(5) 0.07138(18) 0.0629(11) Uani 1 1 d . . .
H18 H -0.1272 0.9947 0.1100 0.075 Uiso 1 1 calc R . .
C19 C 0.37169(18) 1.0687(4) 0.93863(12) 0.0326(7) Uani 1 1 d . . .
C20 C 0.3263(2) 1.0752(4) 0.88207(13) 0.0403(8) Uani 1 1 d . . .
H20 H 0.3093 1.1762 0.8641 0.048 Uiso 1 1 calc R . .
C21 C 0.3064(2) 0.9268(4) 0.85237(13) 0.0416(8) Uani 1 1 d . . .
H21 H 0.2747 0.9291 0.8142 0.050 Uiso 1 1 calc R . .
C22 C 0.33276(18) 0.7747(4) 0.87830(12) 0.0316(7) Uani 1 1 d . . .
C23 C 0.37921(18) 0.7731(4) 0.93495(12) 0.0342(7) Uani 1 1 d . . .
H23 H 0.3979 0.6726 0.9527 0.041 Uiso 1 1 calc R . .
C24 C 0.39851(17) 0.9199(4) 0.96595(13) 0.0350(7) Uani 1 1 d . . .
H24 H 0.4289 0.9179 1.0043 0.042 Uiso 1 1 calc R . .
C25 C 0.0831(2) 0.5718(5) 0.79368(17) 0.0702(12) Uani 1 1 d . . .
H25A H 0.0778 0.6248 0.7582 0.105 Uiso 1 1 calc R . .
H25B H 0.0530 0.6329 0.8131 0.105 Uiso 1 1 calc R . .
H25C H 0.0625 0.4607 0.7868 0.105 Uiso 1 1 calc R . .
C26 C 0.1861(2) 0.5096(5) 0.88704(14) 0.0590(10) Uani 1 1 d . . .
H26A H 0.1866 0.3905 0.8877 0.088 Uiso 1 1 calc R . .
H26B H 0.1447 0.5494 0.9014 0.088 Uiso 1 1 calc R . .
H26C H 0.2379 0.5507 0.9104 0.088 Uiso 1 1 calc R . .
C27 C 0.22565(19) 0.6120(4) 0.80559(13) 0.0369(7) Uani 1 1 d . . .
C28 C 0.31417(18) 0.6144(4) 0.84358(12) 0.0334(7) Uani 1 1 d . . .
H28 H 0.3246 0.5193 0.8694 0.040 Uiso 1 1 calc R . .
C29 C 0.36969(17) 0.6043(4) 0.80736(12) 0.0319(7) Uani 1 1 d . . .
H29A H 0.3583 0.6978 0.7815 0.038 Uiso 1 1 calc R . .
H29B H 0.4255 0.6140 0.8321 0.038 Uiso 1 1 calc R . .
C30 C 0.36087(17) 0.4473(4) 0.77348(12) 0.0330(7) Uani 1 1 d . . .
C31 C 0.40320(17) 0.4398(4) 0.73030(12) 0.0313(7) Uani 1 1 d . . .
C32 C 0.47449(18) 0.5262(4) 0.73690(13) 0.0370(7) Uani 1 1 d . . .
H32 H 0.4979 0.5893 0.7694 0.044 Uiso 1 1 calc R . .
C33 C 0.51084(19) 0.5191(4) 0.69532(14) 0.0434(8) Uani 1 1 d . . .
H33 H 0.5593 0.5751 0.7005 0.052 Uiso 1 1 calc R . .
C34 C 0.4759(2) 0.4301(4) 0.64667(14) 0.0449(8) Uani 1 1 d . . .
H34 H 0.5000 0.4275 0.6185 0.054 Uiso 1 1 calc R . .
C35 C 0.4048(2) 0.3439(4) 0.63955(13) 0.0442(8) Uani 1 1 d . . .
H35 H 0.3809 0.2841 0.6064 0.053 Uiso 1 1 calc R . .
C36 C 0.36921(19) 0.3461(4) 0.68120(13) 0.0393(8) Uani 1 1 d . . .
H36 H 0.3223 0.2850 0.6766 0.047 Uiso 1 1 calc R . .
N1 N 0.10000(19) 0.3452(4) 0.16459(15) 0.0617(9) Uani 1 1 d . . .
N2 N 0.16926(16) 0.5673(4) 0.82900(11) 0.0450(7) Uani 1 1 d . . .
O1 O 0.01775(17) 0.4058(3) 0.07620(11) 0.0698(8) Uani 1 1 d . . .
O2 O -0.01967(15) 0.7702(3) 0.14457(12) 0.0671(8) Uani 1 1 d . . .
O3 O 0.32031(14) 0.3318(3) 0.78024(9) 0.0463(6) Uani 1 1 d . . .
O4 O 0.20744(13) 0.6567(3) 0.75584(9) 0.0503(6) Uani 1 1 d . . .
Br1 Br 0.442910(19) 0.59829(4) 0.084816(14) 0.04186(11) Uani 1 1 d . . .
Br2 Br 0.39635(2) 1.26897(4) 0.981277(14) 0.04170(11) Uani 1 1 d . . .


_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
C1 C2 1.370(4) . ?
C1 C6 1.371(4) . ?
C1 Br1 1.905(3) . ?
C2 C3 1.391(4) . ?
C3 C4 1.385(4) . ?
C4 C5 1.381(4) . ?
C4 C10 1.527(4) . ?
C5 C6 1.388(4) . ?
C7 N1 1.436(5) . ?
C8 N1 1.458(5) . ?
C9 O1 1.226(4) . ?
C9 N1 1.352(4) . ?
C9 C10 1.530(5) . ?
C10 C11 1.520(4) . ?
C11 C12 1.511(5) . ?
C12 O2 1.222(4) . ?
C12 C13 1.472(5) . ?
C13 C14 1.373(5) . ?
C13 C18 1.407(5) . ?
C14 C15 1.402(5) . ?
C15 C16 1.368(6) . ?
C16 C17 1.354(6) . ?
C17 C18 1.385(5) . ?
C19 C20 1.373(4) . ?
C19 C24 1.383(4) . ?
C19 Br2 1.903(3) . ?
C20 C21 1.390(4) . ?
C21 C22 1.392(4) . ?
C22 C23 1.379(4) . ?
C22 C28 1.530(4) . ?
C23 C24 1.394(4) . ?
C25 N2 1.472(4) . ?
C26 N2 1.456(4) . ?
C27 O4 1.229(3) . ?
C27 N2 1.349(4) . ?
C27 C28 1.525(4) . ?
C28 C29 1.530(4) . ?
C29 C30 1.501(4) . ?
C30 O3 1.216(3) . ?
C30 C31 1.495(4) . ?
C31 C32 1.389(4) . ?
C31 C36 1.394(4) . ?
C32 C33 1.384(4) . ?
C33 C34 1.369(4) . ?
C34 C35 1.383(5) . ?
C35 C36 1.375(4) . ?

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 121.2(3) . . ?
C2 C1 Br1 120.3(2) . . ?
C6 C1 Br1 118.5(2) . . ?
C1 C2 C3 119.1(3) . . ?
C4 C3 C2 121.1(3) . . ?
C5 C4 C3 118.1(3) . . ?
C5 C4 C10 120.5(3) . . ?
C3 C4 C10 121.3(3) . . ?
C4 C5 C6 121.4(3) . . ?
C1 C6 C5 119.0(3) . . ?
O1 C9 N1 121.8(3) . . ?
O1 C9 C10 120.0(3) . . ?
N1 C9 C10 118.1(3) . . ?
C11 C10 C4 111.5(3) . . ?
C11 C10 C9 108.8(3) . . ?
C4 C10 C9 110.7(3) . . ?
C12 C11 C10 112.9(3) . . ?
O2 C12 C13 120.6(3) . . ?
O2 C12 C11 120.9(3) . . ?
C13 C12 C11 118.4(3) . . ?
C14 C13 C18 118.5(3) . . ?
C14 C13 C12 122.9(3) . . ?
C18 C13 C12 118.6(3) . . ?
C13 C14 C15 120.5(4) . . ?
C16 C15 C14 119.9(4) . . ?
C17 C16 C15 120.2(4) . . ?
C16 C17 C18 121.0(4) . . ?
C17 C18 C13 119.7(4) . . ?
C20 C19 C24 121.8(3) . . ?
C20 C19 Br2 119.4(2) . . ?
C24 C19 Br2 118.9(2) . . ?
C19 C20 C21 118.3(3) . . ?
C20 C21 C22 121.6(3) . . ?
C23 C22 C21 118.6(3) . . ?
C23 C22 C28 121.0(3) . . ?
C21 C22 C28 120.3(3) . . ?
C22 C23 C24 120.9(3) . . ?
C19 C24 C23 118.9(3) . . ?
O4 C27 N2 122.1(3) . . ?
O4 C27 C28 119.7(3) . . ?
N2 C27 C28 118.0(3) . . ?
C27 C28 C22 110.2(2) . . ?
C27 C28 C29 110.0(2) . . ?
C22 C28 C29 108.8(2) . . ?
C30 C29 C28 114.2(2) . . ?
O3 C30 C31 121.2(3) . . ?
O3 C30 C29 121.6(3) . . ?
C31 C30 C29 117.2(3) . . ?
C32 C31 C36 118.8(3) . . ?
C32 C31 C30 122.1(3) . . ?
C36 C31 C30 119.1(3) . . ?
C33 C32 C31 120.3(3) . . ?
C34 C33 C32 120.4(3) . . ?
C33 C34 C35 119.8(3) . . ?
C36 C35 C34 120.5(3) . . ?
C35 C36 C31 120.2(3) . . ?
C9 N1 C7 124.3(3) . . ?
C9 N1 C8 118.6(4) . . ?
C7 N1 C8 117.0(4) . . ?
C27 N2 C26 125.4(3) . . ?
C27 N2 C25 118.8(3) . . ?
C26 N2 C25 115.8(3) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        26.03
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.606
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.073
_database_code_depnum_ccdc_archive 'CCDC 996425'
