# 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
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# 
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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.
#
data_z

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H14 Br N O2'
_chemical_formula_weight         356.21

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'
Br Br -0.2901 2.4595 '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'

_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                   11.9849(8)
_cell_length_b                   8.8043(6)
_cell_length_c                   14.3967(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.670(2)
_cell_angle_gamma                90.00
_cell_volume                     1516.01(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.561
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             720
_exptl_absorpt_coefficient_mu    2.718
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4412
_exptl_absorpt_correction_T_max  0.5616
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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_reflns_number            16981
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_sigmaI/netI    0.0206
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.70
_diffrn_reflns_theta_max         25.01
_reflns_number_total             2675
_reflns_number_gt                2068
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0454P)²+1.2011P] 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_number_reflns         2675
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0375
_refine_ls_wR_factor_ref         0.1024
_refine_ls_wR_factor_gt          0.0923
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_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
Br1 Br -0.05846(3) 0.24115(5) 0.04578(3) 0.0850(2) Uani 1 1 d . . .
O1 O 0.50476(19) -0.0548(2) 0.38236(17) 0.0715(6) Uani 1 1 d . . .
O2 O 0.25661(16) 0.1199(2) 0.45209(12) 0.0524(5) Uani 1 1 d . . .
N1 N 0.45543(18) 0.1939(2) 0.38321(15) 0.0411(5) Uani 1 1 d . . .
C1 C 0.3744(2) 0.3094(3) 0.39096(17) 0.0395(6) Uani 1 1 d . . .
C2 C 0.4224(2) 0.4463(3) 0.38445(17) 0.0427(6) Uani 1 1 d . . .
C3 C 0.5394(2) 0.4214(3) 0.37269(17) 0.0436(6) Uani 1 1 d . . .
C4 C 0.6293(3) 0.5200(4) 0.3649(2) 0.0612(8) Uani 1 1 d . . .
H4A H 0.6187 0.6246 0.3650 0.073 Uiso 1 1 calc R . .
C5 C 0.7338(3) 0.4592(5) 0.3573(2) 0.0715(10) Uani 1 1 d . . .
H5A H 0.7945 0.5238 0.3522 0.086 Uiso 1 1 calc R . .
C6 C 0.7507(3) 0.3036(5) 0.3568(2) 0.0693(10) Uani 1 1 d . . .
H6A H 0.8225 0.2662 0.3510 0.083 Uiso 1 1 calc R . .
C7 C 0.6634(2) 0.2021(4) 0.3649(2) 0.0558(8) Uani 1 1 d . . .
H7A H 0.6746 0.0976 0.3653 0.067 Uiso 1 1 calc R . .
C8 C 0.5585(2) 0.2650(3) 0.37255(18) 0.0437(6) Uani 1 1 d . . .
C9 C 0.4340(2) 0.0411(3) 0.39038(19) 0.0486(7) Uani 1 1 d . . .
C10 C 0.3142(3) 0.0039(3) 0.4063(2) 0.0549(7) Uani 1 1 d . . .
H10A H 0.2748 -0.0164 0.3466 0.066 Uiso 1 1 calc R . .
H10B H 0.3124 -0.0883 0.4431 0.066 Uiso 1 1 calc R . .
C11 C 0.2565(2) 0.2613(3) 0.40313(19) 0.0440(6) Uani 1 1 d . . .
H11A H 0.2242 0.3371 0.4435 0.053 Uiso 1 1 calc R . .
C12 C 0.1820(2) 0.2561(3) 0.31421(19) 0.0429(6) Uani 1 1 d . . .
C13 C 0.0826(2) 0.1739(4) 0.3113(2) 0.0576(8) Uani 1 1 d . . .
H13A H 0.0638 0.1205 0.3638 0.069 Uiso 1 1 calc R . .
C14 C 0.0116(2) 0.1700(4) 0.2323(2) 0.0617(8) Uani 1 1 d . . .
H14A H -0.0541 0.1136 0.2314 0.074 Uiso 1 1 calc R . .
C15 C 0.0385(2) 0.2501(3) 0.1548(2) 0.0523(7) Uani 1 1 d . . .
C16 C 0.1361(2) 0.3319(3) 0.1548(2) 0.0535(7) Uani 1 1 d . . .
H16A H 0.1540 0.3854 0.1021 0.064 Uiso 1 1 calc R . .
C17 C 0.2074(2) 0.3336(3) 0.23433(18) 0.0473(6) Uani 1 1 d . . .
H17A H 0.2739 0.3880 0.2342 0.057 Uiso 1 1 calc R . .
C34 C 0.3668(3) 0.5981(3) 0.3892(2) 0.0581(8) Uani 1 1 d . . .
H34A H 0.2887 0.5843 0.3975 0.087 Uiso 1 1 calc R . .
H34B H 0.3759 0.6527 0.3324 0.087 Uiso 1 1 calc R . .
H34C H 0.4004 0.6547 0.4407 0.087 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
Br1 C15 1.894(3) . ?
O1 C9 1.208(3) . ?
O2 C10 1.418(3) . ?
O2 C11 1.431(3) . ?
N1 C9 1.374(3) . ?
N1 C8 1.402(4) . ?
N1 C1 1.415(3) . ?
C1 C2 1.342(4) . ?
C1 C11 1.496(4) . ?
C2 C3 1.439(4) . ?
C2 C34 1.497(4) . ?
C3 C4 1.393(4) . ?
C3 C8 1.396(4) . ?
C4 C5 1.374(5) . ?
C4 H4A 0.9300 . ?
C5 C6 1.385(5) . ?
C5 H5A 0.9300 . ?
C6 C7 1.387(5) . ?
C6 H6A 0.9300 . ?
C7 C8 1.384(4) . ?
C7 H7A 0.9300 . ?
C9 C10 1.504(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.514(4) . ?
C11 H11A 0.9800 . ?
C12 C17 1.388(4) . ?
C12 C13 1.392(4) . ?
C13 C14 1.376(4) . ?
C13 H13A 0.9300 . ?
C14 C15 1.376(4) . ?
C14 H14A 0.9300 . ?
C15 C16 1.374(4) . ?
C16 C17 1.384(4) . ?
C16 H16A 0.9300 . ?
C17 H17A 0.9300 . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?

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
C10 O2 C11 112.5(2) . . ?
C9 N1 C8 128.0(2) . . ?
C9 N1 C1 124.4(2) . . ?
C8 N1 C1 107.5(2) . . ?
C2 C1 N1 109.9(2) . . ?
C2 C1 C11 132.4(2) . . ?
N1 C1 C11 117.6(2) . . ?
C1 C2 C3 107.3(2) . . ?
C1 C2 C34 127.2(3) . . ?
C3 C2 C34 125.5(2) . . ?
C4 C3 C8 119.1(3) . . ?
C4 C3 C2 132.7(3) . . ?
C8 C3 C2 108.1(2) . . ?
C5 C4 C3 118.6(3) . . ?
C5 C4 H4A 120.7 . . ?
C3 C4 H4A 120.7 . . ?
C4 C5 C6 121.3(3) . . ?
C4 C5 H5A 119.3 . . ?
C6 C5 H5A 119.3 . . ?
C5 C6 C7 121.7(3) . . ?
C5 C6 H6A 119.1 . . ?
C7 C6 H6A 119.1 . . ?
C8 C7 C6 116.3(3) . . ?
C8 C7 H7A 121.8 . . ?
C6 C7 H7A 121.8 . . ?
C7 C8 C3 123.0(3) . . ?
C7 C8 N1 129.9(3) . . ?
C3 C8 N1 107.1(2) . . ?
O1 C9 N1 122.7(3) . . ?
O1 C9 C10 123.0(3) . . ?
N1 C9 C10 114.2(2) . . ?
O2 C10 C9 114.3(2) . . ?
O2 C10 H10A 108.7 . . ?
C9 C10 H10A 108.7 . . ?
O2 C10 H10B 108.7 . . ?
C9 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
O2 C11 C1 109.4(2) . . ?
O2 C11 C12 111.8(2) . . ?
C1 C11 C12 114.8(2) . . ?
O2 C11 H11A 106.8 . . ?
C1 C11 H11A 106.8 . . ?
C12 C11 H11A 106.8 . . ?
C17 C12 C13 117.6(3) . . ?
C17 C12 C11 122.5(2) . . ?
C13 C12 C11 119.9(2) . . ?
C14 C13 C12 121.4(3) . . ?
C14 C13 H13A 119.3 . . ?
C12 C13 H13A 119.3 . . ?
C15 C14 C13 119.5(3) . . ?
C15 C14 H14A 120.2 . . ?
C13 C14 H14A 120.2 . . ?
C16 C15 C14 120.9(3) . . ?
C16 C15 Br1 119.9(2) . . ?
C14 C15 Br1 119.2(2) . . ?
C15 C16 C17 119.1(3) . . ?
C15 C16 H16A 120.5 . . ?
C17 C16 H16A 120.5 . . ?
C16 C17 C12 121.6(3) . . ?
C16 C17 H17A 119.2 . . ?
C12 C17 H17A 119.2 . . ?
C2 C34 H34A 109.5 . . ?
C2 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C2 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?

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
C9 N1 C1 C2 177.6(2) . . . . ?
C8 N1 C1 C2 0.8(3) . . . . ?
C9 N1 C1 C11 -3.1(4) . . . . ?
C8 N1 C1 C11 -179.9(2) . . . . ?
N1 C1 C2 C3 -0.4(3) . . . . ?
C11 C1 C2 C3 -179.6(3) . . . . ?
N1 C1 C2 C34 -179.9(2) . . . . ?
C11 C1 C2 C34 0.9(5) . . . . ?
C1 C2 C3 C4 -177.9(3) . . . . ?
C34 C2 C3 C4 1.6(4) . . . . ?
C1 C2 C3 C8 0.0(3) . . . . ?
C34 C2 C3 C8 179.5(2) . . . . ?
C8 C3 C4 C5 0.1(4) . . . . ?
C2 C3 C4 C5 177.8(3) . . . . ?
C3 C4 C5 C6 0.2(5) . . . . ?
C4 C5 C6 C7 -0.6(5) . . . . ?
C5 C6 C7 C8 0.6(4) . . . . ?
C6 C7 C8 C3 -0.3(4) . . . . ?
C6 C7 C8 N1 -178.8(3) . . . . ?
C4 C3 C8 C7 -0.1(4) . . . . ?
C2 C3 C8 C7 -178.3(2) . . . . ?
C4 C3 C8 N1 178.7(2) . . . . ?
C2 C3 C8 N1 0.5(3) . . . . ?
C9 N1 C8 C7 1.2(4) . . . . ?
C1 N1 C8 C7 177.9(3) . . . . ?
C9 N1 C8 C3 -177.4(2) . . . . ?
C1 N1 C8 C3 -0.7(3) . . . . ?
C8 N1 C9 O1 -4.7(4) . . . . ?
C1 N1 C9 O1 179.1(3) . . . . ?
C8 N1 C9 C10 176.9(2) . . . . ?
C1 N1 C9 C10 0.8(4) . . . . ?
C11 O2 C10 C9 57.6(3) . . . . ?
O1 C9 C10 O2 154.4(3) . . . . ?
N1 C9 C10 O2 -27.2(3) . . . . ?
C10 O2 C11 C1 -57.4(3) . . . . ?
C10 O2 C11 C12 71.0(3) . . . . ?
C2 C1 C11 O2 -150.4(3) . . . . ?
N1 C1 C11 O2 30.5(3) . . . . ?
C2 C1 C11 C12 82.9(4) . . . . ?
N1 C1 C11 C12 -96.2(3) . . . . ?
O2 C11 C12 C17 -145.2(3) . . . . ?
C1 C11 C12 C17 -19.8(4) . . . . ?
O2 C11 C12 C13 36.2(3) . . . . ?
C1 C11 C12 C13 161.7(3) . . . . ?
C17 C12 C13 C14 -0.3(5) . . . . ?
C11 C12 C13 C14 178.3(3) . . . . ?
C12 C13 C14 C15 -0.7(5) . . . . ?
C13 C14 C15 C16 1.1(5) . . . . ?
C13 C14 C15 Br1 178.9(2) . . . . ?
C14 C15 C16 C17 -0.4(5) . . . . ?
Br1 C15 C16 C17 -178.2(2) . . . . ?
C15 C16 C17 C12 -0.7(4) . . . . ?
C13 C12 C17 C16 1.0(4) . . . . ?
C11 C12 C17 C16 -177.6(3) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.485
_refine_diff_density_min         -0.567
_refine_diff_density_rms         0.048
_database_code_depnum_ccdc_archive 'CCDC 961877'
