# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_B1
_database_code_depnum_ccdc_archive 'CCDC 1403910'
_audit_update_record             
;
2015-05-29 deposited with the CCDC.
2015-06-19 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT057_B1                  
;
PROBLEM: Correction for Absorption Required   RT(exp) ...       1.69 Do !  
RESPONSE: As this is organic ligand, no absorption correction was 
performed
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2014
_chemical_formula_moiety         'C17 H15 N2 O, Br'
_chemical_formula_sum            'C17 H15 Br N2 O'
_chemical_formula_weight         343.22

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.8274(2)
_cell_length_b                   8.3498(2)
_cell_length_c                   14.5138(4)
_cell_angle_alpha                90.1471(10)
_cell_angle_beta                 101.3231(10)
_cell_angle_gamma                107.6322(9)
_cell_volume                     771.47(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9985
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      28.33

_exptl_crystal_description       Rectangular
_exptl_crystal_colour            yellow
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    2.664
_shelx_estimated_absorpt_T_min   0.456
_shelx_estimated_absorpt_T_max   0.777
_exptl_absorpt_correction_type   none

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11522
_diffrn_reflns_av_unetI/netI     0.0123
_diffrn_reflns_av_R_equivalents  0.0175
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.855
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             2681
_reflns_number_gt                2588
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0682P)²+1.1508P] 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     SHELXL
_refine_ls_extinction_coef       0.057(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2681
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0394
_refine_ls_wR_factor_ref         0.1211
_refine_ls_wR_factor_gt          0.1194
_refine_ls_goodness_of_fit_ref   1.135
_refine_ls_restrained_S_all      1.135
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.05707(5) 0.42781(4) 0.28102(2) 0.0402(2) Uani 1 1 d . . . . .
C1 C 0.5537(8) 0.7841(7) 0.4324(4) 0.0616(12) Uani 1 1 d . . . . .
H1 H 0.6706 0.7969 0.4059 0.074 Uiso 1 1 calc R U . . .
C2 C 0.5474(9) 0.7163(7) 0.5162(4) 0.0680(13) Uani 1 1 d . . . . .
H2 H 0.6600 0.6827 0.5469 0.082 Uiso 1 1 calc R U . . .
C3 C 0.3749(10) 0.6957(8) 0.5573(4) 0.0743(15) Uani 1 1 d . . . . .
H3 H 0.3680 0.6430 0.6135 0.089 Uiso 1 1 calc R U . . .
C4 C 0.2173(10) 0.7531(8) 0.5148(4) 0.0713(14) Uani 1 1 d . . . . .
H4 H 0.1033 0.7426 0.5430 0.086 Uiso 1 1 calc R U . . .
C5 C 0.2231(8) 0.8287(6) 0.4285(3) 0.0584(11) Uani 1 1 d . . . . .
C6 C 0.0907(8) 0.9769(7) 0.3149(4) 0.0597(11) Uani 1 1 d . . . . .
H6 H -0.0055 1.0336 0.2927 0.072 Uiso 1 1 calc R U . . .
C7 C 0.2478(8) 0.9842(6) 0.2641(3) 0.0562(11) Uani 1 1 d . . . . .
C8 C 0.2628(8) 1.0757(7) 0.1767(4) 0.0626(12) Uani 1 1 d . . . . .
H8A H 0.2138 1.1726 0.1805 0.075 Uiso 1 1 calc R U . . .
H8B H 0.1740 1.0023 0.1228 0.075 Uiso 1 1 calc R U . . .
C9 C 0.4891(8) 1.1335(6) 0.1638(4) 0.0597(11) Uani 1 1 d . . . . .
H9A H 0.4962 1.1846 0.1041 0.072 Uiso 1 1 calc R U . . .
H9B H 0.5756 1.2170 0.2138 0.072 Uiso 1 1 calc R U . . .
C10 C 0.5687(7) 0.9852(6) 0.1659(3) 0.0518(10) Uani 1 1 d . . . . .
C11 C 0.6766(8) 0.9548(7) 0.1009(3) 0.0583(11) Uani 1 1 d . . . . .
H11 H 0.7132 1.0342 0.0574 0.070 Uiso 1 1 calc R U . . .
C12 C 0.7327(8) 0.8083(7) 0.0984(3) 0.0584(11) Uani 1 1 d . . . . .
C13 C 0.6790(8) 0.6897(7) 0.1638(4) 0.0640(12) Uani 1 1 d . . . . .
H13 H 0.7139 0.5905 0.1624 0.077 Uiso 1 1 calc R U . . .
C14 C 0.5754(8) 0.7193(6) 0.2298(4) 0.0588(11) Uani 1 1 d . . . . .
H14 H 0.5403 0.6396 0.2734 0.071 Uiso 1 1 calc R U . . .
C15 C 0.5203(7) 0.8682(6) 0.2334(3) 0.0532(10) Uani 1 1 d . . . . .
C16 C 0.3868(7) 0.8982(6) 0.2955(3) 0.0514(10) Uani 1 1 d . . . . .
C17 C 0.8857(16) 0.6412(11) 0.0207(6) 0.109(3) Uani 1 1 d . . . . .
H17A H 0.9745 0.6530 -0.0242 0.163 Uiso 1 1 calc R U . . .
H17B H 0.7591 0.5496 -0.0005 0.163 Uiso 1 1 calc R U . . .
H17C H 0.9580 0.6189 0.0806 0.163 Uiso 1 1 calc R U . . .
N1 N 0.3871(6) 0.8354(5) 0.3848(3) 0.0547(9) Uani 1 1 d . . . . .
N2 N 0.0701(7) 0.8961(6) 0.3910(3) 0.0662(11) Uani 1 1 d . . . . .
O2 O 0.8352(7) 0.7916(6) 0.0300(3) 0.0778(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 1.346(7) . ?
C1 N1 1.394(6) . ?
C1 H1 0.9300 . ?
C2 C3 1.389(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.350(9) . ?
C3 H3 0.9300 . ?
C4 C5 1.407(7) . ?
C4 H4 0.9300 . ?
C5 N2 1.356(7) . ?
C5 N1 1.378(6) . ?
C6 N2 1.305(7) . ?
C6 C7 1.403(7) . ?
C6 H6 0.9300 . ?
C7 C16 1.367(7) . ?
C7 C8 1.488(7) . ?
C8 C9 1.522(7) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.494(7) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.372(7) . ?
C10 C15 1.400(7) . ?
C11 C12 1.391(7) . ?
C11 H11 0.9300 . ?
C12 O2 1.352(6) . ?
C12 C13 1.392(7) . ?
C13 C14 1.360(7) . ?
C13 H13 0.9300 . ?
C14 C15 1.408(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.471(6) . ?
C16 N1 1.400(6) . ?
C17 O2 1.412(8) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 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
C2 C1 N1 120.7(5) . . ?
C2 C1 H1 119.6 . . ?
N1 C1 H1 119.6 . . ?
C1 C2 C3 120.8(5) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 H2 119.6 . . ?
C4 C3 C2 119.2(5) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C3 C4 C5 120.9(5) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
N2 C5 N1 121.5(4) . . ?
N2 C5 C4 119.4(5) . . ?
N1 C5 C4 119.0(5) . . ?
N2 C6 C7 124.6(5) . . ?
N2 C6 H6 117.7 . . ?
C7 C6 H6 117.7 . . ?
C16 C7 C6 117.8(5) . . ?
C16 C7 C8 119.6(4) . . ?
C6 C7 C8 122.6(4) . . ?
C7 C8 C9 110.2(4) . . ?
C7 C8 H8A 109.6 . . ?
C9 C8 H8A 109.6 . . ?
C7 C8 H8B 109.6 . . ?
C9 C8 H8B 109.6 . . ?
H8A C8 H8B 108.1 . . ?
C10 C9 C8 109.2(4) . . ?
C10 C9 H9A 109.8 . . ?
C8 C9 H9A 109.8 . . ?
C10 C9 H9B 109.8 . . ?
C8 C9 H9B 109.8 . . ?
H9A C9 H9B 108.3 . . ?
C11 C10 C15 119.1(4) . . ?
C11 C10 C9 122.3(4) . . ?
C15 C10 C9 118.5(4) . . ?
C10 C11 C12 121.7(5) . . ?
C10 C11 H11 119.2 . . ?
C12 C11 H11 119.2 . . ?
O2 C12 C11 116.1(4) . . ?
O2 C12 C13 124.7(5) . . ?
C11 C12 C13 119.2(4) . . ?
C14 C13 C12 119.9(5) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C13 C14 C15 121.2(5) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
C10 C15 C14 118.9(4) . . ?
C10 C15 C16 116.9(4) . . ?
C14 C15 C16 123.6(4) . . ?
C7 C16 N1 117.5(4) . . ?
C7 C16 C15 119.4(4) . . ?
N1 C16 C15 123.0(4) . . ?
O2 C17 H17A 109.5 . . ?
O2 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O2 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C5 N1 C1 118.9(4) . . ?
C5 N1 C16 119.7(4) . . ?
C1 N1 C16 121.4(4) . . ?
C6 N2 C5 117.4(4) . . ?
C12 O2 C17 118.6(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
N1 C1 C2 C3 0.0(8) . . . . ?
C1 C2 C3 C4 -3.6(9) . . . . ?
C2 C3 C4 C5 1.9(9) . . . . ?
C3 C4 C5 N2 -175.2(5) . . . . ?
C3 C4 C5 N1 3.5(8) . . . . ?
N2 C6 C7 C16 1.2(8) . . . . ?
N2 C6 C7 C8 179.0(5) . . . . ?
C16 C7 C8 C9 -29.2(6) . . . . ?
C6 C7 C8 C9 153.1(5) . . . . ?
C7 C8 C9 C10 54.7(5) . . . . ?
C8 C9 C10 C11 133.7(5) . . . . ?
C8 C9 C10 C15 -42.5(6) . . . . ?
C15 C10 C11 C12 2.2(7) . . . . ?
C9 C10 C11 C12 -173.9(5) . . . . ?
C10 C11 C12 O2 178.8(4) . . . . ?
C10 C11 C12 C13 -0.3(8) . . . . ?
O2 C12 C13 C14 -179.9(5) . . . . ?
C11 C12 C13 C14 -0.9(8) . . . . ?
C12 C13 C14 C15 0.2(8) . . . . ?
C11 C10 C15 C14 -2.9(7) . . . . ?
C9 C10 C15 C14 173.4(4) . . . . ?
C11 C10 C15 C16 -174.2(4) . . . . ?
C9 C10 C15 C16 2.1(6) . . . . ?
C13 C14 C15 C10 1.7(7) . . . . ?
C13 C14 C15 C16 172.4(5) . . . . ?
C6 C7 C16 N1 -11.5(7) . . . . ?
C8 C7 C16 N1 170.7(4) . . . . ?
C6 C7 C16 C15 165.5(4) . . . . ?
C8 C7 C16 C15 -12.4(7) . . . . ?
C10 C15 C16 C7 27.5(6) . . . . ?
C14 C15 C16 C7 -143.3(5) . . . . ?
C10 C15 C16 N1 -155.7(4) . . . . ?
C14 C15 C16 N1 33.5(7) . . . . ?
N2 C5 N1 C1 171.7(5) . . . . ?
C4 C5 N1 C1 -7.0(7) . . . . ?
N2 C5 N1 C16 -6.3(7) . . . . ?
C4 C5 N1 C16 175.0(5) . . . . ?
C2 C1 N1 C5 5.4(7) . . . . ?
C2 C1 N1 C16 -176.7(5) . . . . ?
C7 C16 N1 C5 14.1(6) . . . . ?
C15 C16 N1 C5 -162.8(4) . . . . ?
C7 C16 N1 C1 -163.8(5) . . . . ?
C15 C16 N1 C1 19.3(7) . . . . ?
C7 C6 N2 C5 6.7(8) . . . . ?
N1 C5 N2 C6 -4.1(7) . . . . ?
C4 C5 N2 C6 174.6(5) . . . . ?
C11 C12 O2 C17 -176.5(6) . . . . ?
C13 C12 O2 C17 2.5(9) . . . . ?

_refine_diff_density_max         0.576
_refine_diff_density_min         -0.447
_refine_diff_density_rms         0.100

_shelxl_version_number           2014-3



