# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1870916'
_audit_update_record             
;
2018-10-01 deposited with the CCDC.
2018-12-06 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-97
_audit_creation_date             2018-07-09
_chemical_formula_sum            'C25 H24 Br N3 O'
_chemical_formula_weight         462.380
_refine_ls_R_factor_all          0.106
_cell_length_a                   10.1801(4)
_cell_length_b                   10.2257(14)
_cell_length_c                   21.1176(12)
_cell_angle_alpha                90.000
_cell_angle_beta                 103.581(10)
_cell_angle_gamma                90.000
_cell_volume                     2136.8(3)
_cell_formula_units_Z            4
_symmetry_int_tables_number      14
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_symmetry_space_group_name_Hall  -P_2yn

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,1/2+y,1/2-z
3 -x,-y,-z
4 1/2+x,1/2-y,1/2+z

loop_
_atom_type_symbol
_atom_type_oxidation_number
_atom_type_radius_bond
O ? 1.200
Br ? 1.200
N ? 1.200
C ? 1.200
H ? 1.200


loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_Wyckoff_symbol
_atom_site_attached_hydrogens
_atom_site_calc_flag
_atom_site_thermal_displace_type
_atom_site_u_iso_or_equiv
O1 O -0.1707(3) 0.2150(3) 0.7647(1) 1.000 4 e ? d Uani 0.0667(8)
Br1 Br -0.1143(0) -0.2101(0) 0.5317(0) 1.000 4 e ? d Uani 0.0733(2)
N1 N 0.0513(4) 0.2503(3) 0.7783(1) 1.000 4 e ? d Uani 0.0479(8)
N2 N 0.1751(3) 0.1853(3) 0.7806(1) 1.000 4 e ? d Uani 0.0382(7)
N3 N 0.0868(3) 0.2779(3) 0.8917(1) 1.000 4 e ? d Uani 0.0460(8)
C1 C 0.5674(5) 0.0430(5) 0.8197(2) 1.000 4 e ? d Uani 0.0671(13)
H1A H 0.6220 0.0621 0.7912 1.000 4 e ? calc Uiso 0.08000
C2 C 0.6140(5) -0.0379(5) 0.8704(3) 1.000 4 e ? d Uani 0.0724(14)
H2A H 0.7013 -0.0710 0.8775 1.000 4 e ? calc Uiso 0.08700
C3 C 0.5340(5) -0.0715(4) 0.9116(2) 1.000 4 e ? d Uani 0.0677(13)
H3A H 0.5649 -0.1299 0.9456 1.000 4 e ? calc Uiso 0.08100
C4 C 0.4088(4) -0.0182(4) 0.9020(2) 1.000 4 e ? d Uani 0.050(1)
H4A H 0.3550 -0.0389 0.9306 1.000 4 e ? calc Uiso 0.06000
C5 C 0.3594(4) 0.0657(3) 0.8511(2) 1.000 4 e ? d Uani 0.0412(9)
C6 C 0.4390(4) 0.0984(4) 0.8091(2) 1.000 4 e ? d Uani 0.0492(10)
C7 C 0.3874(4) 0.1864(4) 0.7524(2) 1.000 4 e ? d Uani 0.0564(11)
H7A H 0.3548 0.1338 0.7136 1.000 4 e ? calc Uiso 0.06800
H7B H 0.4609 0.2405 0.7452 1.000 4 e ? calc Uiso 0.06800
C8 C 0.2756(4) 0.2722(4) 0.7631(2) 1.000 4 e ? d Uani 0.0521(10)
H8A H 0.3095 0.3341 0.7980 1.000 4 e ? calc Uiso 0.06200
H8B H 0.2358 0.3207 0.7238 1.000 4 e ? calc Uiso 0.06200
C9 C 0.2229(3) 0.1266(3) 0.8450(2) 1.000 4 e ? d Uani 0.0386(9)
H9A H 0.1605 0.0551 0.8479 1.000 4 e ? calc Uiso 0.04600
C10 C 0.2190(4) 0.2191(4) 0.9000(2) 1.000 4 e ? d Uani 0.0449(9)
H10A H 0.2414 0.1719 0.9410 1.000 4 e ? calc Uiso 0.05400
H10B H 0.2861 0.2872 0.9017 1.000 4 e ? calc Uiso 0.05400
C11 C 0.0524(4) 0.3442(4) 0.8298(2) 1.000 4 e ? d Uani 0.0523(10)
H11A H 0.1180 0.4124 0.8286 1.000 4 e ? calc Uiso 0.06300
H11B H -0.0359 0.3846 0.8238 1.000 4 e ? calc Uiso 0.06300
C12 C -0.0654(4) 0.1860(4) 0.7514(2) 1.000 4 e ? d Uani 0.0456(10)
C13 C -0.0624(4) 0.0850(4) 0.7015(2) 1.000 4 e ? d Uani 0.0434(9)
C14 C 0.0064(4) 0.1017(4) 0.6531(2) 1.000 4 e ? d Uani 0.050(1)
H14A H 0.0630 0.1735 0.6543 1.000 4 e ? calc Uiso 0.06000
C15 C -0.0080(4) 0.0131(4) 0.6030(2) 1.000 4 e ? d Uani 0.0476(10)
H15A H 0.0378 0.0250 0.5701 1.000 4 e ? calc Uiso 0.05700
C16 C -0.0903(4) -0.0923(4) 0.6020(2) 1.000 4 e ? d Uani 0.0473(10)
C17 C -0.1574(4) -0.1138(4) 0.6501(2) 1.000 4 e ? d Uani 0.0477(10)
H17A H -0.2111 -0.1876 0.6495 1.000 4 e ? calc Uiso 0.05700
C18 C -0.1430(4) -0.0226(4) 0.6995(2) 1.000 4 e ? d Uani 0.0484(10)
H18A H -0.1893 -0.0346 0.7321 1.000 4 e ? calc Uiso 0.05800
C19 C 0.0780(4) 0.3638(4) 0.9445(2) 1.000 4 e ? d Uani 0.0583(11)
H19A H 0.0024 0.4229 0.9299 1.000 4 e ? calc Uiso 0.07000
H19B H 0.1596 0.4162 0.9558 1.000 4 e ? calc Uiso 0.07000
C20 C 0.0605(4) 0.2942(4) 1.0038(2) 1.000 4 e ? d Uani 0.0465(10)
C21 C -0.0258(4) 0.1884(5) 0.9981(2) 1.000 4 e ? d Uani 0.0686(13)
H21A H -0.0687 0.1578 0.9570 1.000 4 e ? calc Uiso 0.08200
C22 C -0.0487(5) 0.1291(5) 1.0514(2) 1.000 4 e ? d Uani 0.0829(15)
H22A H -0.1095 0.0598 1.0462 1.000 4 e ? calc Uiso 0.09900
C23 C 0.0142(5) 0.1674(5) 1.1123(2) 1.000 4 e ? d Uani 0.0740(13)
H23A H -0.0011 0.1240 1.1486 1.000 4 e ? calc Uiso 0.08900
C24 C 0.0998(5) 0.2703(5) 1.1191(2) 1.000 4 e ? d Uani 0.0658(13)
H24A H 0.1417 0.3001 1.1605 1.000 4 e ? calc Uiso 0.07900
C25 C 0.1250(4) 0.3306(4) 1.0655(2) 1.000 4 e ? d Uani 0.0542(11)
H25A H 0.1877 0.3983 1.0712 1.000 4 e ? calc Uiso 0.06500



loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C12 . . 1.207(4) no
Br1 C16 . . 1.883(4) no
N1 C12 . . 1.360(5) no
N1 N2 . . 1.415(4) no
N1 C11 . . 1.450(4) no
N2 C9 . . 1.462(4) no
N2 C8 . . 1.466(4) no
N3 C19 . . 1.439(4) no
N3 C11 . . 1.440(4) no
N3 C10 . . 1.447(4) no
C1 C2 . . 1.348(6) no
C1 C6 . . 1.394(5) no
C1 H1A . . 0.9300 no
C2 C3 . . 1.366(6) no
C2 H2A . . 0.9300 no
C3 C4 . . 1.357(5) no
C3 H3A . . 0.9300 no
C4 C5 . . 1.375(5) no
C4 H4A . . 0.9300 no
C5 C6 . . 1.375(5) no
C5 C9 . . 1.501(5) no
C6 C7 . . 1.492(5) no
C7 C8 . . 1.497(5) no
C7 H7A . . 0.9700 no
C7 H7B . . 0.9700 no
C8 H8A . . 0.9700 no
C8 H8B . . 0.9700 no
C9 C10 . . 1.506(5) no
C9 H9A . . 0.9800 no
C10 H10A . . 0.9700 no
C10 H10B . . 0.9700 no
C11 H11A . . 0.9700 no
C11 H11B . . 0.9700 no
C12 C13 . . 1.480(5) no
C13 C14 . . 1.379(5) no
C13 C18 . . 1.367(5) no
C14 C15 . . 1.374(5) no
C14 H14A . . 0.9300 no
C15 C16 . . 1.362(5) no
C15 H15A . . 0.9300 no
C16 C17 . . 1.368(5) no
C17 C18 . . 1.381(5) no
C17 H17A . . 0.9300 no
C18 H18A . . 0.9300 no
C19 C20 . . 1.488(5) no
C19 H19A . . 0.9700 no
C19 H19B . . 0.9700 no
C20 C25 . . 1.367(5) no
C20 C21 . . 1.381(5) no
C21 C22 . . 1.346(6) no
C21 H21A . . 0.9300 no
C22 C23 . . 1.353(6) no
C22 H22A . . 0.9300 no
C23 C24 . . 1.352(6) no
C23 H23A . . 0.9300 no
C24 C25 . . 1.364(5) no
C24 H24A . . 0.9300 no
C25 H25A . . 0.9300 no

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C12 N1 N2 . . . 118.1(3) no
C12 N1 C11 . . . 119.1(3) no
N2 N1 C11 . . . 115.8(3) no
N1 N2 C9 . . . 108.9(3) no
N1 N2 C8 . . . 112.0(3) no
C9 N2 C8 . . . 112.6(3) no
C19 N3 C11 . . . 111.7(3) no
C19 N3 C10 . . . 112.6(3) no
C11 N3 C10 . . . 109.1(3) no
C2 C1 C6 . . . 121.2(4) no
C2 C1 H1A . . . 119.40 no
C6 C1 H1A . . . 119.40 no
C1 C2 C3 . . . 120.6(4) no
C1 C2 H2A . . . 119.70 no
C3 C2 H2A . . . 119.70 no
C2 C3 C4 . . . 118.9(4) no
C2 C3 H3A . . . 120.60 no
C4 C3 H3A . . . 120.60 no
C5 C4 C3 . . . 121.7(4) no
C5 C4 H4A . . . 119.20 no
C3 C4 H4A . . . 119.20 no
C4 C5 C6 . . . 119.6(4) no
C4 C5 C9 . . . 119.2(3) no
C6 C5 C9 . . . 121.2(3) no
C5 C6 C1 . . . 118.0(4) no
C5 C6 C7 . . . 121.0(4) no
C1 C6 C7 . . . 120.9(4) no
C6 C7 C8 . . . 111.6(3) no
C6 C7 H7A . . . 109.30 no
C8 C7 H7A . . . 109.30 no
C6 C7 H7B . . . 109.30 no
C8 C7 H7B . . . 109.30 no
H7A C7 H7B . . . 108.00 no
N2 C8 C7 . . . 106.4(3) no
N2 C8 H8A . . . 110.40 no
C7 C8 H8A . . . 110.40 no
N2 C8 H8B . . . 110.40 no
C7 C8 H8B . . . 110.40 no
H8A C8 H8B . . . 108.60 no
N2 C9 C5 . . . 110.4(3) no
N2 C9 C10 . . . 113.4(3) no
C5 C9 C10 . . . 112.7(3) no
N2 C9 H9A . . . 106.60 no
C5 C9 H9A . . . 106.60 no
C10 C9 H9A . . . 106.60 no
N3 C10 C9 . . . 111.0(3) no
N3 C10 H10A . . . 109.40 no
C9 C10 H10A . . . 109.40 no
N3 C10 H10B . . . 109.40 no
C9 C10 H10B . . . 109.40 no
H10A C10 H10B . . . 108.00 no
N3 C11 N1 . . . 109.0(3) no
N3 C11 H11A . . . 109.90 no
N1 C11 H11A . . . 109.90 no
N3 C11 H11B . . . 109.90 no
N1 C11 H11B . . . 109.90 no
H11A C11 H11B . . . 108.30 no
O1 C12 N1 . . . 121.3(4) no
O1 C12 C13 . . . 120.3(4) no
N1 C12 C13 . . . 118.2(4) no
C14 C13 C18 . . . 118.8(4) no
C14 C13 C12 . . . 122.7(4) no
C18 C13 C12 . . . 118.1(3) no
C15 C14 C13 . . . 120.5(4) no
C15 C14 H14A . . . 119.70 no
C13 C14 H14A . . . 119.70 no
C14 C15 C16 . . . 119.1(4) no
C14 C15 H15A . . . 120.40 no
C16 C15 H15A . . . 120.40 no
C15 C16 C17 . . . 121.9(4) no
C15 C16 Br1 . . . 118.9(3) no
C17 C16 Br1 . . . 119.2(3) no
C16 C17 C18 . . . 118.0(4) no
C16 C17 H17A . . . 121.00 no
C18 C17 H17A . . . 121.00 no
C13 C18 C17 . . . 121.6(4) no
C13 C18 H18A . . . 119.20 no
C17 C18 H18A . . . 119.20 no
N3 C19 C20 . . . 113.7(3) no
N3 C19 H19A . . . 108.80 no
C20 C19 H19A . . . 108.80 no
N3 C19 H19B . . . 108.80 no
C20 C19 H19B . . . 108.80 no
H19A C19 H19B . . . 107.70 no
C25 C20 C21 . . . 116.7(4) no
C25 C20 C19 . . . 123.2(4) no
C21 C20 C19 . . . 120.1(3) no
C22 C21 C20 . . . 120.8(4) no
C22 C21 H21A . . . 119.60 no
C20 C21 H21A . . . 119.60 no
C21 C22 C23 . . . 121.9(5) no
C21 C22 H22A . . . 119.10 no
C23 C22 H22A . . . 119.10 no
C24 C23 C22 . . . 118.4(5) no
C24 C23 H23A . . . 120.80 no
C22 C23 H23A . . . 120.80 no
C23 C24 C25 . . . 120.4(4) no
C23 C24 H24A . . . 119.80 no
C25 C24 H24A . . . 119.80 no
C24 C25 C20 . . . 121.7(4) no
C24 C25 H25A . . . 119.20 no
C20 C25 H25A . . . 119.20 no
