# 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_g140609a
_database_code_depnum_ccdc_archive 'CCDC 1045560'
_audit_update_record             
;
2015-01-26 deposited with the CCDC.
2015-05-14 downloaded from the CCDC.
;
_audit_creation_method           'Created with Diamond (www.crystalimpact.com)'
_audit_creation_date             14-08-28
_chemical_formula_sum            'C18 H20 Br N O2'
_chemical_formula_weight         362.260
_refine_ls_R_factor_all          0.042
_cell_length_a                   7.9136(3)
_cell_length_b                   10.4625(5)
_cell_length_c                   11.1965(5)
_cell_angle_alpha                68.134(5)
_cell_angle_beta                 76.650(4)
_cell_angle_gamma                87.633(4)
_cell_volume                     836.1(1)
_cell_formula_units_Z            2

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 'x, y, z'

loop_
_atom_type_symbol
_atom_type_oxidation_number
_atom_type_radius_bond
Br ? 1.200
O ? 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
Br1 Br 0.774() 1.0341(0) 0.4125(0) 1.000 ? ? ? d Uani 0.04893(13)
O1 O 0.6565(2) 0.7292(2) 0.2855(2) 1.000 ? ? ? d Uani 0.0440(4)
O2 O 0.7312(3) 0.5319(2) 0.2105(2) 1.000 ? ? ? d Uani 0.0529(5)
N1 N 0.7468(3) 0.5078(2) 0.3407(2) 1.000 ? ? ? d Uani 0.0463(5)
C1 C 0.6747(3) 1.0869(2) 0.0960(2) 1.000 ? ? ? d Uani 0.0349(5)
C2 C 0.8550(3) 1.1217(3) 0.0505(2) 1.000 ? ? ? d Uani 0.0399(5)
H2 H 0.9315 1.0643 0.0953 1.000 ? ? ? calc Uiso 0.04800
C3 C 0.9199(4) 1.2371(3) -0.0573(3) 1.000 ? ? ? d Uani 0.0485(6)
H3 H 1.0392 1.2572 -0.0849 1.000 ? ? ? calc Uiso 0.05800
C4 C 0.8075(4) 1.3258(3) -0.1269(3) 1.000 ? ? ? d Uani 0.0554(7)
H4 H 0.8526 1.4045 -0.2003 1.000 ? ? ? calc Uiso 0.06600
C5 C 0.6343(4) 1.2972(3) -0.0874(3) 1.000 ? ? ? d Uani 0.0517(7)
H5 H 0.5613 1.3563 -0.1348 1.000 ? ? ? calc Uiso 0.06200
C6 C 0.5608(3) 1.1783(3) 0.0254(2) 1.000 ? ? ? d Uani 0.0415(6)
C7 C 0.3796(4) 1.1479(3) 0.0669(3) 1.000 ? ? ? d Uani 0.0510(7)
H7 H 0.3058 1.2077 0.0211 1.000 ? ? ? calc Uiso 0.06100
C8 C 0.3117(3) 1.0327(3) 0.1725(3) 1.000 ? ? ? d Uani 0.0502(7)
H8 H 0.1921 1.0139 0.1989 1.000 ? ? ? calc Uiso 0.06000
C9 C 0.4230(3) 0.9411(3) 0.2427(3) 1.000 ? ? ? d Uani 0.0420(6)
H9 H 0.3754 0.8622 0.3149 1.000 ? ? ? calc Uiso 0.05000
C10 C 0.5993(3) 0.9661(2) 0.2065(2) 1.000 ? ? ? d Uani 0.0336(5)
C11 C 0.7101(3) 0.8612(2) 0.2840(2) 1.000 ? ? ? d Uani 0.0325(5)
H11 H 0.8324 0.8829 0.2368 1.000 ? ? ? calc Uiso 0.03900
C12 C 0.6906(3) 0.8544(2) 0.4255(2) 1.000 ? ? ? d Uani 0.0338(5)
H12 H 0.5665 0.8418 0.4687 1.000 ? ? ? calc Uiso 0.04100
C13 C 0.7846(3) 0.7354(2) 0.5092(2) 1.000 ? ? ? d Uani 0.0400(5)
C14 C 0.7048(4) 0.6059(3) 0.5067(3) 1.000 ? ? ? d Uani 0.0492(6)
H14A H 0.7668 0.5267 0.5502 1.000 ? ? ? calc Uiso 0.05900
H14B H 0.5848 0.5920 0.5566 1.000 ? ? ? calc Uiso 0.05900
C15 C 0.7102(3) 0.6133(2) 0.3704(3) 1.000 ? ? ? d Uani 0.0394(5)
C16 C 0.7469(5) 0.7294(3) 0.6513(3) 1.000 ? ? ? d Uani 0.0615(8)
H16A H 0.8044 0.8072 0.6535 1.000 ? ? ? calc Uiso 0.09200
H16B H 0.7887 0.6458 0.7061 1.000 ? ? ? calc Uiso 0.09200
H16C H 0.6238 0.7315 0.6836 1.000 ? ? ? calc Uiso 0.09200
C17 C 0.9809(3) 0.7459(3) 0.4527(3) 1.000 ? ? ? d Uani 0.0518(7)
H17A H 1.0042 0.7416 0.3663 1.000 ? ? ? calc Uiso 0.07800
H17B H 1.0337 0.6709 0.5098 1.000 ? ? ? calc Uiso 0.07800
H17C H 1.0282 0.8318 0.4465 1.000 ? ? ? calc Uiso 0.07800
C18 C 0.7878(5) 0.4156(4) 0.1791(4) 1.000 ? ? ? d Uani 0.0731(10)
H18A H 0.7895 0.4348 0.0880 1.000 ? ? ? calc Uiso 0.11000
H18B H 0.7095 0.3376 0.2346 1.000 ? ? ? calc Uiso 0.11000
H18C H 0.9026 0.3956 0.1934 1.000 ? ? ? calc Uiso 0.11000



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
Br1 C12 . . 1.960(2) no
O1 C11 . . 1.454(3) no
O1 C15 . . 1.357(3) no
O2 N1 . . 1.417(3) no
O2 C18 . . 1.417(4) no
N1 C15 . . 1.270(3) no
C1 C2 . . 1.413(3) no
C1 C6 . . 1.430(3) no
C1 C10 . . 1.428(3) no
C2 H2 . . 0.9300 no
C2 C3 . . 1.363(4) no
C3 H3 . . 0.9300 no
C3 C4 . . 1.405(4) no
C4 H4 . . 0.9300 no
C4 C5 . . 1.349(4) no
C5 H5 . . 0.9300 no
C5 C6 . . 1.426(4) no
C6 C7 . . 1.412(4) no
C7 H7 . . 0.9300 no
C7 C8 . . 1.356(4) no
C8 H8 . . 0.9300 no
C8 C9 . . 1.414(4) no
C9 H9 . . 0.9300 no
C9 C10 . . 1.367(3) no
C10 C11 . . 1.513(3) no
C11 H11 . . 0.9800 no
C11 C12 . . 1.530(3) no
C12 H12 . . 0.9800 no
C12 C13 . . 1.536(3) no
C13 C14 . . 1.531(4) no
C13 C16 . . 1.527(4) no
C13 C17 . . 1.528(4) no
C14 H14A . . 0.9700 no
C14 H14B . . 0.9700 no
C14 C15 . . 1.490(4) no
C16 H16A . . 0.9600 no
C16 H16B . . 0.9600 no
C16 H16C . . 0.9600 no
C17 H17A . . 0.9600 no
C17 H17B . . 0.9600 no
C17 H17C . . 0.9600 no
C18 H18A . . 0.9600 no
C18 H18B . . 0.9600 no
C18 H18C . . 0.9600 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
C15 O1 C11 . . . 117.82(17) no
N1 O2 C18 . . . 108.8(2) no
C15 N1 O2 . . . 111.5(2) no
C2 C1 C6 . . . 117.5(2) no
C2 C1 C10 . . . 124.4(2) no
C10 C1 C6 . . . 118.1(2) no
C1 C2 H2 . . . 119.10 no
C3 C2 C1 . . . 121.9(2) no
C3 C2 H2 . . . 119.10 no
C2 C3 H3 . . . 119.80 no
C2 C3 C4 . . . 120.4(3) no
C4 C3 H3 . . . 119.80 no
C3 C4 H4 . . . 119.90 no
C5 C4 C3 . . . 120.1(3) no
C5 C4 H4 . . . 119.90 no
C4 C5 H5 . . . 119.30 no
C4 C5 C6 . . . 121.4(2) no
C6 C5 H5 . . . 119.30 no
C5 C6 C1 . . . 118.8(2) no
C7 C6 C1 . . . 119.7(2) no
C7 C6 C5 . . . 121.5(2) no
C6 C7 H7 . . . 119.50 no
C8 C7 C6 . . . 120.9(2) no
C8 C7 H7 . . . 119.50 no
C7 C8 H8 . . . 120.10 no
C7 C8 C9 . . . 119.9(2) no
C9 C8 H8 . . . 120.10 no
C8 C9 H9 . . . 119.30 no
C10 C9 C8 . . . 121.4(3) no
C10 C9 H9 . . . 119.30 no
C1 C10 C11 . . . 121.7(2) no
C9 C10 C1 . . . 120.1(2) no
C9 C10 C11 . . . 118.2(2) no
O1 C11 C10 . . . 105.61(17) no
O1 C11 H11 . . . 108.90 no
O1 C11 C12 . . . 110.26(18) no
C10 C11 H11 . . . 108.90 no
C10 C11 C12 . . . 114.03(18) no
C12 C11 H11 . . . 108.90 no
Br1 C12 H12 . . . 108.00 no
C11 C12 Br1 . . . 107.05(15) no
C11 C12 H12 . . . 108.00 no
C11 C12 C13 . . . 113.70(19) no
C13 C12 Br1 . . . 111.85(15) no
C13 C12 H12 . . . 108.00 no
C14 C13 C12 . . . 104.29(19) no
C16 C13 C12 . . . 110.2(2) no
C16 C13 C14 . . . 109.6(2) no
C17 C13 C12 . . . 112.8(2) no
C17 C13 C14 . . . 110.0(2) no
C17 C13 C16 . . . 109.8(2) no
C13 C14 H14A . . . 108.90 no
C13 C14 H14B . . . 108.90 no
H14A C14 H14B . . . 107.80 no
C15 C14 C13 . . . 113.2(2) no
C15 C14 H14A . . . 108.90 no
C15 C14 H14B . . . 108.90 no
O1 C15 C14 . . . 118.0(2) no
N1 C15 O1 . . . 121.6(2) no
N1 C15 C14 . . . 120.0(2) no
C13 C16 H16A . . . 109.50 no
C13 C16 H16B . . . 109.50 no
C13 C16 H16C . . . 109.50 no
H16A C16 H16B . . . 109.50 no
H16A C16 H16C . . . 109.50 no
H16B C16 H16C . . . 109.50 no
C13 C17 H17A . . . 109.50 no
C13 C17 H17B . . . 109.50 no
C13 C17 H17C . . . 109.50 no
H17A C17 H17B . . . 109.50 no
H17A C17 H17C . . . 109.50 no
H17B C17 H17C . . . 109.50 no
O2 C18 H18A . . . 109.50 no
O2 C18 H18B . . . 109.50 no
O2 C18 H18C . . . 109.50 no
H18A C18 H18B . . . 109.50 no
H18A C18 H18C . . . 109.50 no
H18B C18 H18C . . . 109.50 no

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
Br1 C12 C13 C14 . . . . -179.41(16) no
Br1 C12 C13 C16 . . . . 63.0(2) no
Br1 C12 C13 C17 . . . . -60.0(2) no
O1 C11 C12 Br1 . . . . 177.92(13) no
O1 C11 C12 C13 . . . . 53.9(2) no
O2 N1 C15 O1 . . . . 2.6(3) no
O2 N1 C15 C14 . . . . 175.1(2) no
C1 C2 C3 C4 . . . . 0.1(4) no
C1 C6 C7 C8 . . . . -0.3(4) no
C1 C10 C11 O1 . . . . -126.6(2) no
C1 C10 C11 C12 . . . . 112.2(2) no
C2 C1 C6 C5 . . . . 1.1(3) no
C2 C1 C6 C7 . . . . 179.9(2) no
C2 C1 C10 C9 . . . . -179.7(2) no
C2 C1 C10 C11 . . . . -1.3(4) no
C2 C3 C4 C5 . . . . -0.1(4) no
C3 C4 C5 C6 . . . . 0.6(4) no
C4 C5 C6 C1 . . . . -1.1(4) no
C4 C5 C6 C7 . . . . -179.9(3) no
C5 C6 C7 C8 . . . . 178.4(3) no
C6 C1 C2 C3 . . . . -0.6(4) no
C6 C1 C10 C9 . . . . -0.5(3) no
C6 C1 C10 C11 . . . . 177.88(19) no
C6 C7 C8 C9 . . . . -0.1(4) no
C7 C8 C9 C10 . . . . 0.2(4) no
C8 C9 C10 C1 . . . . 0.1(4) no
C8 C9 C10 C11 . . . . -178.3(2) no
C9 C10 C11 O1 . . . . 51.9(3) no
C9 C10 C11 C12 . . . . -69.3(3) no
C10 C1 C2 C3 . . . . 178.6(2) no
C10 C1 C6 C5 . . . . -178.2(2) no
C10 C1 C6 C7 . . . . 0.6(3) no
C10 C11 C12 Br1 . . . . -63.5(2) no
C10 C11 C12 C13 . . . . 172.48(19) no
C11 O1 C15 N1 . . . . -145.3(2) no
C11 O1 C15 C14 . . . . 42.0(3) no
C11 C12 C13 C14 . . . . -58.0(3) no
C11 C12 C13 C16 . . . . -175.6(2) no
C11 C12 C13 C17 . . . . 61.4(3) no
C12 C13 C14 C15 . . . . 52.7(3) no
C13 C14 C15 O1 . . . . -47.7(3) no
C13 C14 C15 N1 . . . . 139.5(2) no
C15 O1 C11 C10 . . . . -167.18(19) no
C15 O1 C11 C12 . . . . -43.5(3) no
C16 C13 C14 C15 . . . . 170.6(2) no
C17 C13 C14 C15 . . . . -68.6(3) no
C18 O2 N1 C15 . . . . 175.1(3) no
####################################################################### 
# 
# 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_g140915b
_database_code_depnum_ccdc_archive 'CCDC 1045561'
_audit_update_record             
;
2015-01-26 deposited with the CCDC.
2015-05-14 downloaded from the CCDC.
;
_audit_creation_date             2014-09-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.02.28 svn.r2899 for OlexSys, GUI svn.r4781)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C18 H18 Br N O2'
_chemical_formula_sum            'C18 H18 Br N O2'
_chemical_formula_weight         360.24
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   8.2950(4)
_cell_length_b                   10.0959(4)
_cell_length_c                   11.1296(5)
_cell_angle_alpha                114.134(4)
_cell_angle_beta                 108.692(4)
_cell_angle_gamma                90.710(4)
_cell_volume                     794.56(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3184
_cell_measurement_temperature    223.00(10)
_cell_measurement_theta_max      27.7640
_cell_measurement_theta_min      3.2070
_exptl_absorpt_coefficient_mu    2.593
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85349
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.506
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             368
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_unetI/netI     0.0451
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8528
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.16
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      223.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4471
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0330573000
_diffrn_orient_matrix_UB_12      0.0761845000
_diffrn_orient_matrix_UB_13      0.0308851000
_diffrn_orient_matrix_UB_21      0.0541399000
_diffrn_orient_matrix_UB_22      -0.0046282000
_diffrn_orient_matrix_UB_23      0.0615875000
_diffrn_orient_matrix_UB_31      0.0659961000
_diffrn_orient_matrix_UB_32      -0.0163992000
_diffrn_orient_matrix_UB_33      -0.0290037000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2683
_reflns_number_total             3261
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         1.438
_refine_diff_density_min         -0.843
_refine_diff_density_rms         0.082
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.278
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3261
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0731
_refine_ls_R_factor_gt           0.0573
_refine_ls_restrained_S_all      1.278
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1770
_refine_ls_wR_factor_ref         0.1889
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Br1 Br 1.14795(7) -0.13256(5) 0.09050(5) 0.0520(3) Uani 1 d . . .
O1 O 0.8890(4) -0.0203(3) 0.2788(3) 0.0364(7) Uani 1 d . . .
O2 O 0.6893(4) -0.1536(3) 0.3402(3) 0.0356(7) Uani 1 d . . .
N1 N 0.6885(4) 0.0018(3) 0.3881(4) 0.0298(8) Uani 1 d . . .
C1 C 1.1687(6) 0.0292(6) 0.2689(5) 0.0473(12) Uani 1 d . . .
H1A H 1.2066 -0.0029 0.3431 0.057 Uiso 1 calc . . R
H1B H 1.2552 0.1094 0.2909 0.057 Uiso 1 calc . . R
C2 C 1.0004(6) 0.0825(5) 0.2638(6) 0.0427(11) Uani 1 d . . .
H2 H 0.9445 0.0891 0.1749 0.051 Uiso 1 calc . . R
C3 C 1.0130(6) 0.2286(5) 0.3894(5) 0.0374(10) Uani 1 d . . .
H3A H 1.0442 0.3123 0.3748 0.045 Uiso 1 calc . . R
H3B H 1.0960 0.2346 0.4766 0.045 Uiso 1 calc . . R
C4 C 0.8274(5) 0.2196(4) 0.3897(4) 0.0266(8) Uani 1 d . . .
C5 C 0.7937(5) 0.0569(4) 0.3537(4) 0.0285(9) Uani 1 d . . .
C6 C 0.8184(5) 0.3221(4) 0.5331(4) 0.0253(8) Uani 1 d . . .
C7 C 0.9223(5) 0.3080(5) 0.6528(5) 0.0349(10) Uani 1 d . . .
H7 H 0.9898 0.2341 0.6438 0.042 Uiso 1 calc . . R
C8 C 0.9244(6) 0.4047(5) 0.7849(5) 0.0407(11) Uani 1 d . . .
H8 H 0.9950 0.3958 0.8643 0.049 Uiso 1 calc . . R
C9 C 0.8227(6) 0.5144(5) 0.8004(5) 0.0390(10) Uani 1 d . . .
H9 H 0.8241 0.5784 0.8893 0.047 Uiso 1 calc . . R
C10 C 0.7200(5) 0.5268(5) 0.6826(5) 0.0356(10) Uani 1 d . . .
H10 H 0.6517 0.6001 0.6917 0.043 Uiso 1 calc . . R
C11 C 0.7173(5) 0.4309(4) 0.5497(4) 0.0307(9) Uani 1 d . . .
H11 H 0.6462 0.4402 0.4709 0.037 Uiso 1 calc . . R
C12 C 0.7057(5) 0.2476(4) 0.2676(4) 0.0283(9) Uani 1 d . . .
C13 C 0.7516(6) 0.3654(5) 0.2438(5) 0.0417(11) Uani 1 d . . .
H13 H 0.8559 0.4282 0.3029 0.050 Uiso 1 calc . . R
C14 C 0.6459(7) 0.3903(6) 0.1349(6) 0.0508(13) Uani 1 d . . .
H14 H 0.6797 0.4688 0.1200 0.061 Uiso 1 calc . . R
C15 C 0.4884(7) 0.2989(6) 0.0466(5) 0.0499(13) Uani 1 d . . .
H15 H 0.4169 0.3154 -0.0277 0.060 Uiso 1 calc . . R
C16 C 0.4396(7) 0.1846(5) 0.0699(5) 0.0446(11) Uani 1 d . . .
H16 H 0.3340 0.1234 0.0115 0.053 Uiso 1 calc . . R
C17 C 0.5462(5) 0.1591(4) 0.1796(4) 0.0332(9) Uani 1 d . . .
H17 H 0.5107 0.0815 0.1949 0.040 Uiso 1 calc . . R
C18 C 0.5420(6) -0.2164(5) 0.3492(6) 0.0450(12) Uani 1 d . . .
H18A H 0.4410 -0.2242 0.2726 0.067 Uiso 1 calc . . GR
H18B H 0.5294 -0.1549 0.4370 0.067 Uiso 1 calc . . GR
H18C H 0.5560 -0.3126 0.3443 0.067 Uiso 1 calc . . GR


_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 C1 1.940(5) . ?
O1 C2 1.474(5) . ?
O1 C5 1.355(5) . ?
O2 N1 1.436(4) . ?
O2 C18 1.420(5) . ?
N1 C5 1.263(5) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.495(7) . ?
C2 H2 0.9800 . ?
C2 C3 1.535(6) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.542(5) . ?
C4 C5 1.522(5) . ?
C4 C6 1.533(5) . ?
C4 C12 1.545(6) . ?
C6 C7 1.400(6) . ?
C6 C11 1.378(6) . ?
C7 H7 0.9300 . ?
C7 C8 1.387(6) . ?
C8 H8 0.9300 . ?
C8 C9 1.389(7) . ?
C9 H9 0.9300 . ?
C9 C10 1.372(7) . ?
C10 H10 0.9300 . ?
C10 C11 1.390(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.393(6) . ?
C12 C17 1.390(6) . ?
C13 H13 0.9300 . ?
C13 C14 1.369(7) . ?
C14 H14 0.9300 . ?
C14 C15 1.389(8) . ?
C15 H15 0.9300 . ?
C15 C16 1.365(8) . ?
C16 H16 0.9300 . ?
C16 C17 1.382(7) . ?
C17 H17 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 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
C5 O1 C2 109.0(3) . . ?
C18 O2 N1 107.9(3) . . ?
C5 N1 O2 110.0(3) . . ?
Br1 C1 H1A 109.4 . . ?
Br1 C1 H1B 109.4 . . ?
H1A C1 H1B 108.0 . . ?
C2 C1 Br1 111.1(3) . . ?
C2 C1 H1A 109.4 . . ?
C2 C1 H1B 109.4 . . ?
O1 C2 C1 108.7(4) . . ?
O1 C2 H2 110.4 . . ?
O1 C2 C3 102.1(3) . . ?
C1 C2 H2 110.4 . . ?
C1 C2 C3 114.4(4) . . ?
C3 C2 H2 110.4 . . ?
C2 C3 H3A 111.4 . . ?
C2 C3 H3B 111.4 . . ?
C2 C3 C4 101.6(3) . . ?
H3A C3 H3B 109.3 . . ?
C4 C3 H3A 111.4 . . ?
C4 C3 H3B 111.4 . . ?
C3 C4 C12 109.8(3) . . ?
C5 C4 C3 98.2(3) . . ?
C5 C4 C6 113.8(3) . . ?
C5 C4 C12 109.3(3) . . ?
C6 C4 C3 112.2(3) . . ?
C6 C4 C12 112.7(3) . . ?
O1 C5 C4 111.2(3) . . ?
N1 C5 O1 124.8(4) . . ?
N1 C5 C4 124.0(4) . . ?
C7 C6 C4 118.5(3) . . ?
C11 C6 C4 122.8(4) . . ?
C11 C6 C7 118.7(4) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 C6 119.8(4) . . ?
C8 C7 H7 120.1 . . ?
C7 C8 H8 119.5 . . ?
C7 C8 C9 121.0(4) . . ?
C9 C8 H8 119.5 . . ?
C8 C9 H9 120.5 . . ?
C10 C9 C8 118.9(4) . . ?
C10 C9 H9 120.5 . . ?
C9 C10 H10 119.7 . . ?
C9 C10 C11 120.6(4) . . ?
C11 C10 H10 119.7 . . ?
C6 C11 C10 121.0(4) . . ?
C6 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C13 C12 C4 120.6(4) . . ?
C17 C12 C4 121.8(4) . . ?
C17 C12 C13 117.6(4) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 C12 121.2(4) . . ?
C14 C13 H13 119.4 . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 120.2(5) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 H15 120.3 . . ?
C16 C15 C14 119.4(5) . . ?
C16 C15 H15 120.3 . . ?
C15 C16 H16 119.8 . . ?
C15 C16 C17 120.4(5) . . ?
C17 C16 H16 119.8 . . ?
C12 C17 H17 119.5 . . ?
C16 C17 C12 121.1(4) . . ?
C16 C17 H17 119.5 . . ?
O2 C18 H18A 109.5 . . ?
O2 C18 H18B 109.5 . . ?
O2 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
Br1 C1 C2 O1 78.1(4) . . . . ?
Br1 C1 C2 C3 -168.6(3) . . . . ?
O1 C2 C3 C4 -39.4(4) . . . . ?
O2 N1 C5 O1 1.9(6) . . . . ?
O2 N1 C5 C4 -179.1(3) . . . . ?
C1 C2 C3 C4 -156.6(4) . . . . ?
C2 O1 C5 N1 -178.1(4) . . . . ?
C2 O1 C5 C4 2.8(5) . . . . ?
C2 C3 C4 C5 39.3(4) . . . . ?
C2 C3 C4 C6 159.2(4) . . . . ?
C2 C3 C4 C12 -74.7(4) . . . . ?
C3 C4 C5 O1 -27.2(4) . . . . ?
C3 C4 C5 N1 153.7(4) . . . . ?
C3 C4 C6 C7 -55.5(5) . . . . ?
C3 C4 C6 C11 121.9(4) . . . . ?
C3 C4 C12 C13 -47.0(5) . . . . ?
C3 C4 C12 C17 134.2(4) . . . . ?
C4 C6 C7 C8 176.3(4) . . . . ?
C4 C6 C11 C10 -176.4(3) . . . . ?
C4 C12 C13 C14 179.2(4) . . . . ?
C4 C12 C17 C16 -179.3(4) . . . . ?
C5 O1 C2 C1 144.5(4) . . . . ?
C5 O1 C2 C3 23.3(5) . . . . ?
C5 C4 C6 C7 54.9(4) . . . . ?
C5 C4 C6 C11 -127.7(4) . . . . ?
C5 C4 C12 C13 -153.7(4) . . . . ?
C5 C4 C12 C17 27.5(5) . . . . ?
C6 C4 C5 O1 -145.9(3) . . . . ?
C6 C4 C5 N1 35.0(5) . . . . ?
C6 C4 C12 C13 78.8(5) . . . . ?
C6 C4 C12 C17 -99.9(4) . . . . ?
C6 C7 C8 C9 0.9(7) . . . . ?
C7 C6 C11 C10 1.1(6) . . . . ?
C7 C8 C9 C10 -0.4(7) . . . . ?
C8 C9 C10 C11 0.2(6) . . . . ?
C9 C10 C11 C6 -0.6(6) . . . . ?
C11 C6 C7 C8 -1.3(6) . . . . ?
C12 C4 C5 O1 87.2(4) . . . . ?
C12 C4 C5 N1 -91.9(5) . . . . ?
C12 C4 C6 C7 179.9(3) . . . . ?
C12 C4 C6 C11 -2.6(5) . . . . ?
C12 C13 C14 C15 0.9(8) . . . . ?
C13 C12 C17 C16 1.9(6) . . . . ?
C13 C14 C15 C16 0.4(8) . . . . ?
C14 C15 C16 C17 -0.5(7) . . . . ?
C15 C16 C17 C12 -0.7(7) . . . . ?
C17 C12 C13 C14 -2.0(7) . . . . ?
C18 O2 N1 C5 -165.8(4) . . . . ?

