# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1045078'
_audit_update_record             
;
2015-01-23 deposited with the CCDC.
2015-02-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H18 Br N3 O'
_chemical_formula_sum            'C26 H18 Br N3 O'
_chemical_formula_weight         468.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   11.7456(2)
_cell_length_b                   13.5528(3)
_cell_length_c                   13.0646(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2079.70(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    20263
_cell_measurement_theta_min      6.50
_cell_measurement_theta_max      68.20

_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_F_000             952
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    2.880
_shelx_estimated_absorpt_T_min   0.597
_shelx_estimated_absorpt_T_max   0.597
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.362
_exptl_absorpt_correction_T_max  0.487
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku Saturn944+ CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27739
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         6.533
_diffrn_reflns_theta_max         68.303
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             3780
_reflns_number_gt                3388
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.746
_reflns_Friedel_fraction_max     0.986
_reflns_Friedel_fraction_full    0.990

_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       'CrystalClear-SM 2.0 r4 (Rigaku, 2009)'
_computing_cell_refinement       'CrystalClear-SM Auto 2.0 r4'
_computing_data_reduction        'CrystalClear-SM Auto 2.0 r4'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2009)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0462P)²+0.7157P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_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 x determined using 1317 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.019(5)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3780
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0362
_refine_ls_wR_factor_ref         0.0967
_refine_ls_wR_factor_gt          0.0882
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_restrained_S_all      1.125
_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 0.13307(5) 0.19455(5) 1.04751(4) 0.0765(2) Uani 1 1 d . . . . .
O1 O 0.7430(2) 0.1767(2) 0.6788(3) 0.0611(8) Uani 1 1 d . . . . .
N1 N 0.1851(3) 0.0749(3) 0.6611(3) 0.0619(10) Uani 1 1 d . . . . .
H1 H 0.1253 0.0392 0.6524 0.074 Uiso 1 1 calc R U . . .
N2 N 0.5605(3) 0.1325(2) 0.6337(3) 0.0400(7) Uani 1 1 d . . . . .
N3 N 0.4241(3) 0.1925(3) 0.3875(2) 0.0426(7) Uani 1 1 d . . . . .
H3 H 0.3748 0.2392 0.3908 0.051 Uiso 1 1 calc R U . . .
C1 C 0.5735(4) 0.0430(4) 0.1501(4) 0.0617(12) Uani 1 1 d . . . . .
H1A H 0.6105 0.0084 0.0985 0.074 Uiso 1 1 calc R U . . .
C2 C 0.5981(4) 0.0219(4) 0.2503(4) 0.0556(11) Uani 1 1 d . . . . .
H2 H 0.6498 -0.0275 0.2670 0.067 Uiso 1 1 calc R U . . .
C3 C 0.5435(4) 0.0764(3) 0.3268(3) 0.0447(9) Uani 1 1 d . . . . .
C4 C 0.5484(3) 0.0759(3) 0.4365(3) 0.0424(9) Uani 1 1 d . . . . .
C5 C 0.4752(3) 0.1477(3) 0.4699(3) 0.0397(8) Uani 1 1 d . . . . .
C6 C 0.4618(3) 0.1784(3) 0.5806(3) 0.0372(8) Uani 1 1 d . . . . .
C7 C 0.3512(3) 0.1500(3) 0.6293(3) 0.0397(8) Uani 1 1 d . . . . .
C8 C 0.3144(3) 0.1773(3) 0.7303(3) 0.0393(8) Uani 1 1 d . . . . .
C9 C 0.2101(3) 0.1283(3) 0.7478(3) 0.0458(9) Uani 1 1 d . . . . .
C10 C 0.1535(4) 0.1315(4) 0.8412(4) 0.0559(11) Uani 1 1 d . . . . .
H10 H 0.0859 0.0973 0.8521 0.067 Uiso 1 1 calc R U . . .
C11 C 0.2027(4) 0.1878(3) 0.9163(3) 0.0524(10) Uani 1 1 d . . . . .
C12 C 0.2701(4) 0.0876(3) 0.5910(4) 0.0536(11) Uani 1 1 d . . . . .
H12 H 0.2725 0.0582 0.5268 0.064 Uiso 1 1 calc R U . . .
C13 C 0.5839(4) 0.0283(3) 0.6160(3) 0.0461(9) Uani 1 1 d . . . . .
H13A H 0.5166 -0.0104 0.6317 0.055 Uiso 1 1 calc R U . . .
H13B H 0.6449 0.0067 0.6607 0.055 Uiso 1 1 calc R U . . .
C14 C 0.6181(4) 0.0116(3) 0.5045(3) 0.0502(10) Uani 1 1 d . . . . .
H14A H 0.6982 0.0267 0.4956 0.060 Uiso 1 1 calc R U . . .
H14B H 0.6063 -0.0571 0.4863 0.060 Uiso 1 1 calc R U . . .
C15 C 0.4646(4) 0.1504(3) 0.2985(3) 0.0437(9) Uani 1 1 d . . . . .
C16 C 0.4379(4) 0.1705(3) 0.1972(3) 0.0524(10) Uani 1 1 d . . . . .
H16 H 0.3849 0.2186 0.1796 0.063 Uiso 1 1 calc R U . . .
C17 C 0.4935(4) 0.1157(4) 0.1238(4) 0.0595(12) Uani 1 1 d . . . . .
H17 H 0.4777 0.1271 0.0550 0.071 Uiso 1 1 calc R U . . .
C18 C 0.6446(3) 0.1985(3) 0.6539(3) 0.0435(8) Uani 1 1 d . . . . .
C19 C 0.5954(3) 0.2974(3) 0.6386(3) 0.0401(8) Uani 1 1 d . . . . .
C20 C 0.6375(4) 0.3901(3) 0.6650(3) 0.0520(10) Uani 1 1 d . . . . .
H20 H 0.7093 0.3972 0.6940 0.062 Uiso 1 1 calc R U . . .
C21 C 0.5697(5) 0.4705(3) 0.6467(3) 0.0567(12) Uani 1 1 d . . . . .
H21 H 0.5966 0.5333 0.6621 0.068 Uiso 1 1 calc R U . . .
C22 C 0.4619(5) 0.4596(3) 0.6058(4) 0.0581(12) Uani 1 1 d . . . . .
H22 H 0.4170 0.5153 0.5955 0.070 Uiso 1 1 calc R U . . .
C23 C 0.4192(4) 0.3676(3) 0.5799(3) 0.0502(10) Uani 1 1 d . . . . .
H23 H 0.3465 0.3605 0.5526 0.060 Uiso 1 1 calc R U . . .
C24 C 0.4885(3) 0.2871(3) 0.5961(3) 0.0392(8) Uani 1 1 d . . . . .
C25 C 0.3590(4) 0.2346(3) 0.8092(3) 0.0472(9) Uani 1 1 d . . . . .
H25 H 0.4258 0.2701 0.7990 0.057 Uiso 1 1 calc R U . . .
C26 C 0.3045(4) 0.2389(3) 0.9017(3) 0.0525(10) Uani 1 1 d . . . . .
H26 H 0.3354 0.2759 0.9549 0.063 Uiso 1 1 calc R U . . .


_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 C11 1.902(4) . ?
O1 C18 1.237(5) . ?
N1 C12 1.365(6) . ?
N1 C9 1.376(6) . ?
N1 H1 0.8600 . ?
N2 C18 1.359(5) . ?
N2 C13 1.457(5) . ?
N2 C6 1.486(5) . ?
N3 C5 1.374(5) . ?
N3 C15 1.379(5) . ?
N3 H3 0.8600 . ?
C1 C2 1.370(7) . ?
C1 C17 1.404(8) . ?
C1 H1A 0.9300 . ?
C2 C3 1.399(6) . ?
C2 H2 0.9300 . ?
C3 C15 1.415(6) . ?
C3 C4 1.434(6) . ?
C4 C5 1.369(5) . ?
C4 C14 1.490(6) . ?
C5 C6 1.513(5) . ?
C6 C7 1.496(5) . ?
C6 C24 1.519(5) . ?
C7 C12 1.369(6) . ?
C7 C8 1.436(5) . ?
C8 C25 1.393(5) . ?
C8 C9 1.412(5) . ?
C9 C10 1.391(6) . ?
C10 C11 1.371(7) . ?
C10 H10 0.9300 . ?
C11 C26 1.395(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.528(6) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.387(6) . ?
C16 C17 1.378(7) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 C19 1.472(6) . ?
C19 C24 1.381(5) . ?
C19 C20 1.394(6) . ?
C20 C21 1.371(7) . ?
C20 H20 0.9300 . ?
C21 C22 1.383(8) . ?
C21 H21 0.9300 . ?
C22 C23 1.386(7) . ?
C22 H22 0.9300 . ?
C23 C24 1.378(6) . ?
C23 H23 0.9300 . ?
C25 C26 1.369(6) . ?
C25 H25 0.9300 . ?
C26 H26 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
C12 N1 C9 109.2(3) . . ?
C12 N1 H1 125.4 . . ?
C9 N1 H1 125.4 . . ?
C18 N2 C13 122.1(3) . . ?
C18 N2 C6 112.4(3) . . ?
C13 N2 C6 118.6(3) . . ?
C5 N3 C15 109.1(3) . . ?
C5 N3 H3 125.4 . . ?
C15 N3 H3 125.4 . . ?
C2 C1 C17 121.4(4) . . ?
C2 C1 H1A 119.3 . . ?
C17 C1 H1A 119.3 . . ?
C1 C2 C3 118.4(5) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 H2 120.8 . . ?
C2 C3 C15 119.2(4) . . ?
C2 C3 C4 133.9(4) . . ?
C15 C3 C4 106.9(3) . . ?
C5 C4 C3 106.9(3) . . ?
C5 C4 C14 124.8(4) . . ?
C3 C4 C14 128.3(4) . . ?
C4 C5 N3 109.7(3) . . ?
C4 C5 C6 124.5(3) . . ?
N3 C5 C6 125.6(3) . . ?
N2 C6 C7 111.8(3) . . ?
N2 C6 C5 104.4(3) . . ?
C7 C6 C5 115.2(3) . . ?
N2 C6 C24 100.5(3) . . ?
C7 C6 C24 111.8(3) . . ?
C5 C6 C24 111.9(3) . . ?
C12 C7 C8 106.5(4) . . ?
C12 C7 C6 127.4(4) . . ?
C8 C7 C6 125.9(3) . . ?
C25 C8 C9 117.9(4) . . ?
C25 C8 C7 135.2(4) . . ?
C9 C8 C7 106.8(3) . . ?
N1 C9 C10 129.5(4) . . ?
N1 C9 C8 107.4(4) . . ?
C10 C9 C8 122.9(4) . . ?
C11 C10 C9 116.3(4) . . ?
C11 C10 H10 121.8 . . ?
C9 C10 H10 121.8 . . ?
C10 C11 C26 122.7(4) . . ?
C10 C11 Br1 119.4(3) . . ?
C26 C11 Br1 117.9(3) . . ?
N1 C12 C7 110.0(4) . . ?
N1 C12 H12 125.0 . . ?
C7 C12 H12 125.0 . . ?
N2 C13 C14 110.1(3) . . ?
N2 C13 H13A 109.6 . . ?
C14 C13 H13A 109.6 . . ?
N2 C13 H13B 109.6 . . ?
C14 C13 H13B 109.6 . . ?
H13A C13 H13B 108.1 . . ?
C4 C14 C13 109.7(3) . . ?
C4 C14 H14A 109.7 . . ?
C13 C14 H14A 109.7 . . ?
C4 C14 H14B 109.7 . . ?
C13 C14 H14B 109.7 . . ?
H14A C14 H14B 108.2 . . ?
N3 C15 C16 130.2(4) . . ?
N3 C15 C3 107.3(4) . . ?
C16 C15 C3 122.5(4) . . ?
C17 C16 C15 116.8(4) . . ?
C17 C16 H16 121.6 . . ?
C15 C16 H16 121.6 . . ?
C16 C17 C1 121.7(5) . . ?
C16 C17 H17 119.2 . . ?
C1 C17 H17 119.2 . . ?
O1 C18 N2 124.9(4) . . ?
O1 C18 C19 128.3(4) . . ?
N2 C18 C19 106.7(3) . . ?
C24 C19 C20 120.9(4) . . ?
C24 C19 C18 108.6(3) . . ?
C20 C19 C18 130.4(3) . . ?
C21 C20 C19 117.9(4) . . ?
C21 C20 H20 121.1 . . ?
C19 C20 H20 121.1 . . ?
C20 C21 C22 121.0(4) . . ?
C20 C21 H21 119.5 . . ?
C22 C21 H21 119.5 . . ?
C21 C22 C23 121.5(4) . . ?
C21 C22 H22 119.3 . . ?
C23 C22 H22 119.3 . . ?
C24 C23 C22 117.5(4) . . ?
C24 C23 H23 121.3 . . ?
C22 C23 H23 121.3 . . ?
C23 C24 C19 121.3(3) . . ?
C23 C24 C6 128.7(4) . . ?
C19 C24 C6 109.8(3) . . ?
C26 C25 C8 120.1(4) . . ?
C26 C25 H25 119.9 . . ?
C8 C25 H25 119.9 . . ?
C25 C26 C11 120.0(4) . . ?
C25 C26 H26 120.0 . . ?
C11 C26 H26 120.0 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H3 O1 0.86 2.13 2.902(4) 149.7 2_456

_refine_diff_density_max         0.226
_refine_diff_density_min         -0.599
_refine_diff_density_rms         0.071

_shelxl_version_number           2014-3

