# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_ljh034
_database_code_depnum_ccdc_archive 'CCDC 1438591'
_audit_update_record             
;
2015-11-24 deposited with the CCDC.
2016-07-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H24 Br N O'
_chemical_formula_sum            'C23 H24 Br N O'
_chemical_formula_weight         410.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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           orthorhombic
_symmetry_space_group_name_H-M   Pna21
_symmetry_space_group_name_Hall  P2c-2n

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

_cell_length_a                   11.8036(9)
_cell_length_b                   21.3495(16)
_cell_length_c                   7.9601(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2006.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4493
_cell_measurement_theta_min      1.91
_cell_measurement_theta_max      27.55

_exptl_crystal_description       lump
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      1.359
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             848
_exptl_absorpt_coefficient_mu    2.060
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6487
_exptl_absorpt_correction_T_max  0.7081
_exptl_absorpt_process_details   'SHELXL-97 (Sheldrick, 2008)'

_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11717
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_sigmaI/netI    0.0599
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.91
_diffrn_reflns_theta_max         27.55
_reflns_number_total             4493
_reflns_number_gt                3486
_reflns_threshold_expression     >2sigma(I)

_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-97 (Sheldrick, 2008)'
_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)+(0.0056P)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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.003(7)
_refine_ls_number_reflns         4493
_refine_ls_number_parameters     235
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0318
_refine_ls_wR_factor_ref         0.0707
_refine_ls_wR_factor_gt          0.0656
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_refine_ls_shift/su_max          0.002
_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 0.93800(2) 0.361753(12) 1.24613(5) 0.06449(11) Uani 1 1 d . . .
O1 O 0.80168(18) -0.02561(9) 0.5424(3) 0.0809(7) Uani 1 1 d . . .
N1 N 0.94866(18) 0.04071(10) 0.5627(3) 0.0552(6) Uani 1 1 d . . .
C1 C 0.8363(2) 0.02790(12) 0.5468(4) 0.0524(7) Uani 1 1 d . . .
C2 C 0.7572(2) 0.08477(10) 0.5258(3) 0.0401(5) Uani 1 1 d . . .
C3 C 0.6349(2) 0.06772(12) 0.5735(3) 0.0466(6) Uani 1 1 d . . .
H3A H 0.5842 0.0923 0.5039 0.056 Uiso 1 1 calc R . .
H3B H 0.6227 0.0240 0.5454 0.056 Uiso 1 1 calc R . .
C4 C 0.60102(18) 0.07731(9) 0.7561(4) 0.0424(5) Uani 1 1 d . . .
C5 C 0.6275(2) 0.14485(10) 0.8033(3) 0.0420(6) Uani 1 1 d . . .
H5A H 0.5743 0.1723 0.7466 0.050 Uiso 1 1 calc R . .
H5B H 0.6167 0.1500 0.9233 0.050 Uiso 1 1 calc R . .
C6 C 0.74693(17) 0.16472(8) 0.7584(3) 0.0344(4) Uani 1 1 d . . .
C7 C 0.80476(19) 0.13787(9) 0.6318(3) 0.0349(5) Uani 1 1 d . . .
C8 C 0.92176(19) 0.15355(12) 0.5813(3) 0.0392(5) Uani 1 1 d . . .
C9 C 0.9634(2) 0.21371(13) 0.5564(3) 0.0495(7) Uani 1 1 d . . .
H9 H 0.9168 0.2480 0.5777 0.059 Uiso 1 1 calc R . .
C10 C 1.0727(2) 0.22339(16) 0.5007(4) 0.0608(8) Uani 1 1 d . . .
H10 H 1.0996 0.2640 0.4857 0.073 Uiso 1 1 calc R . .
C11 C 1.1412(3) 0.17361(18) 0.4677(4) 0.0731(9) Uani 1 1 d . . .
H11 H 1.2151 0.1804 0.4312 0.088 Uiso 1 1 calc R . .
C12 C 1.1022(3) 0.11355(17) 0.4881(4) 0.0690(9) Uani 1 1 d . . .
H12 H 1.1494 0.0799 0.4633 0.083 Uiso 1 1 calc R . .
C13 C 0.9940(2) 0.10259(12) 0.5447(3) 0.0487(6) Uani 1 1 d . . .
C14 C 1.0279(3) -0.01241(16) 0.5746(5) 0.0900(12) Uani 1 1 d . . .
H14A H 1.1039 0.0031 0.5853 0.135 Uiso 1 1 calc R . .
H14B H 1.0221 -0.0377 0.4752 0.135 Uiso 1 1 calc R . .
H14C H 1.0094 -0.0373 0.6713 0.135 Uiso 1 1 calc R . .
C15 C 0.7608(2) 0.10195(13) 0.3375(3) 0.0531(7) Uani 1 1 d . . .
H15A H 0.7301 0.0681 0.2726 0.080 Uiso 1 1 calc R . .
H15B H 0.8378 0.1094 0.3043 0.080 Uiso 1 1 calc R . .
H15C H 0.7167 0.1391 0.3186 0.080 Uiso 1 1 calc R . .
C16 C 0.4736(2) 0.06558(13) 0.7731(4) 0.0620(8) Uani 1 1 d . . .
H16A H 0.4511 0.0717 0.8878 0.093 Uiso 1 1 calc R . .
H16B H 0.4567 0.0234 0.7396 0.093 Uiso 1 1 calc R . .
H16C H 0.4331 0.0943 0.7024 0.093 Uiso 1 1 calc R . .
C17 C 0.6655(3) 0.03320(12) 0.8734(4) 0.0610(8) Uani 1 1 d . . .
H17A H 0.6424 0.0407 0.9873 0.092 Uiso 1 1 calc R . .
H17B H 0.7453 0.0406 0.8628 0.092 Uiso 1 1 calc R . .
H17C H 0.6491 -0.0094 0.8437 0.092 Uiso 1 1 calc R . .
C18 C 0.7961(2) 0.21339(10) 0.8712(3) 0.0347(5) Uani 1 1 d . . .
C19 C 0.7410(2) 0.27027(11) 0.8965(3) 0.0461(6) Uani 1 1 d . . .
H19 H 0.6746 0.2787 0.8377 0.055 Uiso 1 1 calc R . .
C20 C 0.7826(2) 0.31434(11) 1.0071(3) 0.0496(6) Uani 1 1 d . . .
H20 H 0.7454 0.3523 1.0225 0.059 Uiso 1 1 calc R . .
C21 C 0.8799(2) 0.30109(10) 1.0936(3) 0.0404(6) Uani 1 1 d . . .
C22 C 0.9368(2) 0.24554(12) 1.0744(3) 0.0473(6) Uani 1 1 d . . .
H22 H 1.0021 0.2374 1.1360 0.057 Uiso 1 1 calc R . .
C23 C 0.8951(2) 0.20185(11) 0.9617(3) 0.0424(6) Uani 1 1 d . . .
H23 H 0.9336 0.1643 0.9461 0.051 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 C21 1.903(2) . ?
O1 C1 1.214(3) . ?
N1 C1 1.360(3) . ?
N1 C13 1.433(3) . ?
N1 C14 1.473(3) . ?
C1 C2 1.541(3) . ?
C2 C7 1.520(3) . ?
C2 C3 1.536(3) . ?
C2 C15 1.544(3) . ?
C3 C4 1.522(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.523(3) . ?
C4 C17 1.529(4) . ?
C4 C16 1.531(3) . ?
C5 C6 1.515(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.345(3) . ?
C6 C18 1.491(3) . ?
C7 C8 1.477(3) . ?
C8 C9 1.389(4) . ?
C8 C13 1.413(3) . ?
C9 C10 1.381(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.361(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.372(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.374(4) . ?
C12 H12 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.393(3) . ?
C18 C23 1.394(3) . ?
C19 C20 1.379(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.368(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.371(3) . ?
C22 C23 1.385(3) . ?
C22 H22 0.9300 . ?
C23 H23 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
C1 N1 C13 122.7(2) . . ?
C1 N1 C14 118.1(3) . . ?
C13 N1 C14 118.6(2) . . ?
O1 C1 N1 121.4(2) . . ?
O1 C1 C2 122.3(3) . . ?
N1 C1 C2 116.3(2) . . ?
C7 C2 C3 112.74(19) . . ?
C7 C2 C1 107.7(2) . . ?
C3 C2 C1 110.9(2) . . ?
C7 C2 C15 110.56(19) . . ?
C3 C2 C15 108.8(2) . . ?
C1 C2 C15 106.0(2) . . ?
C4 C3 C2 116.84(19) . . ?
C4 C3 H3A 108.1 . . ?
C2 C3 H3A 108.1 . . ?
C4 C3 H3B 108.1 . . ?
C2 C3 H3B 108.1 . . ?
H3A C3 H3B 107.3 . . ?
C3 C4 C5 108.0(2) . . ?
C3 C4 C17 111.7(2) . . ?
C5 C4 C17 109.3(2) . . ?
C3 C4 C16 108.7(2) . . ?
C5 C4 C16 109.58(19) . . ?
C17 C4 C16 109.5(2) . . ?
C6 C5 C4 113.46(18) . . ?
C6 C5 H5A 108.9 . . ?
C4 C5 H5A 108.9 . . ?
C6 C5 H5B 108.9 . . ?
C4 C5 H5B 108.9 . . ?
H5A C5 H5B 107.7 . . ?
C7 C6 C18 123.40(19) . . ?
C7 C6 C5 121.99(19) . . ?
C18 C6 C5 114.52(19) . . ?
C6 C7 C8 125.6(2) . . ?
C6 C7 C2 123.1(2) . . ?
C8 C7 C2 111.31(19) . . ?
C9 C8 C13 118.0(2) . . ?
C9 C8 C7 125.4(2) . . ?
C13 C8 C7 116.5(2) . . ?
C10 C9 C8 121.0(3) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C11 C10 C9 120.0(3) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C12 120.5(3) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C11 C12 C13 120.6(3) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C12 C13 C8 119.8(3) . . ?
C12 C13 N1 122.5(2) . . ?
C8 C13 N1 117.7(2) . . ?
N1 C14 H14A 109.5 . . ?
N1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C2 C15 H15A 109.5 . . ?
C2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C4 C16 H16A 109.5 . . ?
C4 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C4 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C4 C17 H17A 109.5 . . ?
C4 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C4 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C23 118.1(2) . . ?
C19 C18 C6 120.8(2) . . ?
C23 C18 C6 120.94(18) . . ?
C20 C19 C18 121.4(2) . . ?
C20 C19 H19 119.3 . . ?
C18 C19 H19 119.3 . . ?
C21 C20 C19 118.7(2) . . ?
C21 C20 H20 120.7 . . ?
C19 C20 H20 120.7 . . ?
C20 C21 C22 122.2(2) . . ?
C20 C21 Br1 118.89(17) . . ?
C22 C21 Br1 118.88(19) . . ?
C21 C22 C23 118.7(2) . . ?
C21 C22 H22 120.6 . . ?
C23 C22 H22 120.6 . . ?
C22 C23 C18 120.9(2) . . ?
C22 C23 H23 119.6 . . ?
C18 C23 H23 119.6 . . ?

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
C13 N1 C1 O1 171.0(3) . . . . ?
C14 N1 C1 O1 -0.1(4) . . . . ?
C13 N1 C1 C2 -6.0(4) . . . . ?
C14 N1 C1 C2 -177.0(3) . . . . ?
O1 C1 C2 C7 147.6(3) . . . . ?
N1 C1 C2 C7 -35.5(3) . . . . ?
O1 C1 C2 C3 23.9(3) . . . . ?
N1 C1 C2 C3 -159.2(2) . . . . ?
O1 C1 C2 C15 -94.0(3) . . . . ?
N1 C1 C2 C15 82.9(3) . . . . ?
C7 C2 C3 C4 -30.7(3) . . . . ?
C1 C2 C3 C4 90.1(3) . . . . ?
C15 C2 C3 C4 -153.7(2) . . . . ?
C2 C3 C4 C5 54.2(3) . . . . ?
C2 C3 C4 C17 -66.0(3) . . . . ?
C2 C3 C4 C16 173.1(2) . . . . ?
C3 C4 C5 C6 -50.4(3) . . . . ?
C17 C4 C5 C6 71.3(3) . . . . ?
C16 C4 C5 C6 -168.7(2) . . . . ?
C4 C5 C6 C7 26.7(3) . . . . ?
C4 C5 C6 C18 -150.1(2) . . . . ?
C18 C6 C7 C8 -2.4(3) . . . . ?
C5 C6 C7 C8 -178.9(2) . . . . ?
C18 C6 C7 C2 175.1(2) . . . . ?
C5 C6 C7 C2 -1.4(3) . . . . ?
C3 C2 C7 C6 2.8(3) . . . . ?
C1 C2 C7 C6 -119.8(2) . . . . ?
C15 C2 C7 C6 124.8(2) . . . . ?
C3 C2 C7 C8 -179.3(2) . . . . ?
C1 C2 C7 C8 58.1(2) . . . . ?
C15 C2 C7 C8 -57.3(3) . . . . ?
C6 C7 C8 C9 -47.9(4) . . . . ?
C2 C7 C8 C9 134.3(2) . . . . ?
C6 C7 C8 C13 136.6(2) . . . . ?
C2 C7 C8 C13 -41.2(3) . . . . ?
C13 C8 C9 C10 -1.2(4) . . . . ?
C7 C8 C9 C10 -176.6(2) . . . . ?
C8 C9 C10 C11 0.6(4) . . . . ?
C9 C10 C11 C12 0.6(5) . . . . ?
C10 C11 C12 C13 -1.1(5) . . . . ?
C11 C12 C13 C8 0.5(4) . . . . ?
C11 C12 C13 N1 178.0(3) . . . . ?
C9 C8 C13 C12 0.6(4) . . . . ?
C7 C8 C13 C12 176.5(2) . . . . ?
C9 C8 C13 N1 -177.0(2) . . . . ?
C7 C8 C13 N1 -1.2(3) . . . . ?
C1 N1 C13 C12 -150.8(3) . . . . ?
C14 N1 C13 C12 20.2(4) . . . . ?
C1 N1 C13 C8 26.8(4) . . . . ?
C14 N1 C13 C8 -162.3(3) . . . . ?
C7 C6 C18 C19 127.4(3) . . . . ?
C5 C6 C18 C19 -55.9(3) . . . . ?
C7 C6 C18 C23 -56.3(3) . . . . ?
C5 C6 C18 C23 120.4(2) . . . . ?
C23 C18 C19 C20 0.3(4) . . . . ?
C6 C18 C19 C20 176.7(2) . . . . ?
C18 C19 C20 C21 -0.4(4) . . . . ?
C19 C20 C21 C22 -0.2(4) . . . . ?
C19 C20 C21 Br1 179.90(19) . . . . ?
C20 C21 C22 C23 1.0(4) . . . . ?
Br1 C21 C22 C23 -179.12(18) . . . . ?
C21 C22 C23 C18 -1.1(4) . . . . ?
C19 C18 C23 C22 0.5(4) . . . . ?
C6 C18 C23 C22 -175.9(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.55
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.039
