# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1477823'
_audit_update_record             
;
2016-05-03 deposited with the CCDC.
2016-10-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H21 Br N2 O3'
_chemical_formula_weight         393.28

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'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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+1/2, -z'

_cell_length_a                   8.8396(3)
_cell_length_b                   17.5572(7)
_cell_length_c                   11.6494(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.347(2)
_cell_angle_gamma                90
_cell_volume                     1802.77(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9919
_cell_measurement_theta_min      4.56
_cell_measurement_theta_max      66.35

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_F_000             808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    3.259
_shelx_estimated_absorpt_T_min   0.696
_shelx_estimated_absorpt_T_max   0.736
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.54
_exptl_absorpt_correction_T_max  0.76
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\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            44389
_diffrn_reflns_av_unetI/netI     0.1401
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.805
_diffrn_reflns_theta_max         67.017
_diffrn_reflns_theta_full        67.000
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.929
_diffrn_reflns_point_group_measured_fraction_full 0.929
_reflns_number_total             44389
_reflns_number_gt                31362
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.814
_reflns_Friedel_fraction_max     0.865
_reflns_Friedel_fraction_full    0.865

_reflns_special_details          
; 
 _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_special_details          
; 
 Refined as a 2-component twin. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1293P)²+0.2665P] 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 1484 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.040(14)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         44389
_refine_ls_number_parameters     440
_refine_ls_number_restraints     261
_refine_ls_R_factor_all          0.1283
_refine_ls_R_factor_gt           0.0825
_refine_ls_wR_factor_ref         0.2326
_refine_ls_wR_factor_gt          0.2026
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.000
_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 0.3794(2) 0.24704(14) 0.43260(15) 0.0266(6) Uani 1 1 d . . . . .
O1 O 0.3707(14) 0.5347(8) 0.0426(10) 0.019(4) Uani 1 1 d . . . . .
O2 O 0.6813(15) 0.3466(8) -0.1702(10) 0.019(3) Uani 1 1 d . . . . .
O3 O 0.4726(14) 0.3986(7) -0.0990(10) 0.017(3) Uani 1 1 d . . . . .
N1 N 0.7026(17) 0.4422(9) -0.0373(13) 0.013(4) Uani 1 1 d . . . . .
N2 N 0.5909(19) 0.6063(11) -0.1548(14) 0.028(5) Uani 1 1 d . . . . .
C1 C 0.412(2) 0.3200(12) 0.3175(16) 0.018(3) Uani 1 1 d . U . . .
C2 C 0.307(2) 0.3743(12) 0.2947(15) 0.019(3) Uani 1 1 d . U . . .
H2 H 0.2176 0.3749 0.3351 0.023 Uiso 1 1 calc R U . . .
C3 C 0.328(2) 0.4296(12) 0.2129(15) 0.020(3) Uani 1 1 d . U . . .
H3 H 0.2544 0.4683 0.1974 0.023 Uiso 1 1 calc R U . . .
C4 C 0.462(2) 0.4282(12) 0.1521(15) 0.018(3) Uani 1 1 d . U . . .
C5 C 0.569(2) 0.3726(11) 0.1777(15) 0.018(3) Uani 1 1 d . U . . .
H5 H 0.6605 0.3723 0.1397 0.022 Uiso 1 1 calc R U . . .
C6 C 0.544(2) 0.3162(12) 0.2601(15) 0.018(3) Uani 1 1 d . U . . .
H6 H 0.6151 0.2765 0.2761 0.022 Uiso 1 1 calc R U . . .
C7 C 0.475(2) 0.4913(12) 0.0642(15) 0.018(3) Uani 1 1 d . U . . .
C8 C 0.626(2) 0.5071(12) 0.0132(16) 0.018(3) Uani 1 1 d . U . . .
C9 C 0.731(2) 0.5403(12) 0.1137(14) 0.018(3) Uani 1 1 d . U . . .
H9A H 0.6830 0.5868 0.1427 0.022 Uiso 1 1 calc R U . . .
H9B H 0.7391 0.5028 0.1772 0.022 Uiso 1 1 calc R U . . .
C10 C 0.891(2) 0.5604(12) 0.0809(16) 0.021(3) Uani 1 1 d . U . . .
H10A H 0.9540 0.5791 0.1491 0.025 Uiso 1 1 calc R U . . .
H10B H 0.8865 0.6007 0.0212 0.025 Uiso 1 1 calc R U . . .
C11 C 0.960(2) 0.4870(12) 0.0346(15) 0.021(3) Uani 1 1 d . U . . .
H11A H 1.0630 0.4976 0.0113 0.026 Uiso 1 1 calc R U . . .
H11B H 0.9679 0.4480 0.0962 0.026 Uiso 1 1 calc R U . . .
C12 C 0.863(2) 0.4570(12) -0.0668(15) 0.020(4) Uani 1 1 d . U . . .
H12A H 0.9073 0.4090 -0.0937 0.024 Uiso 1 1 calc R U . . .
H12B H 0.8616 0.4943 -0.1305 0.024 Uiso 1 1 calc R U . . .
C13 C 0.623(2) 0.3914(11) -0.1102(16) 0.016(4) Uani 1 1 d . . . . .
C14 C 0.362(2) 0.3378(11) -0.1457(16) 0.017(3) Uani 1 1 d . U . . .
C15 C 0.363(2) 0.3340(12) -0.2750(15) 0.019(4) Uani 1 1 d . U . . .
H15A H 0.2825 0.2996 -0.3057 0.029 Uiso 1 1 calc R U . . .
H15B H 0.4615 0.3149 -0.2956 0.029 Uiso 1 1 calc R U . . .
H15C H 0.3456 0.3850 -0.3076 0.029 Uiso 1 1 calc R U . . .
C16 C 0.216(2) 0.3692(12) -0.1096(16) 0.024(4) Uani 1 1 d . U . . .
H16A H 0.1981 0.4197 -0.1437 0.036 Uiso 1 1 calc R U . . .
H16B H 0.2209 0.3733 -0.0255 0.036 Uiso 1 1 calc R U . . .
H16C H 0.1324 0.3351 -0.1358 0.036 Uiso 1 1 calc R U . . .
C17 C 0.3956(19) 0.2597(12) -0.0904(14) 0.020(4) Uani 1 1 d . U . . .
H17A H 0.3802 0.2622 -0.0080 0.030 Uiso 1 1 calc R U . . .
H17B H 0.5009 0.2454 -0.1005 0.030 Uiso 1 1 calc R U . . .
H17C H 0.3271 0.2215 -0.1272 0.030 Uiso 1 1 calc R U . . .
C18 C 0.600(2) 0.5646(12) -0.0790(16) 0.018(3) Uani 1 1 d . U . . .
Br00 Br 1.1167(2) 0.75186(13) 0.96565(15) 0.0279(6) Uani 1 1 d . . . . .
O1A O 1.1572(15) 0.4752(8) 0.5559(11) 0.019(3) Uani 1 1 d . . . . .
O2A O 0.7898(15) 0.6682(8) 0.3624(10) 0.021(3) Uani 1 1 d . . . . .
O3A O 1.0154(14) 0.6110(7) 0.4158(10) 0.014(3) Uani 1 1 d . . . . .
N1A N 0.7980(17) 0.5588(9) 0.4674(12) 0.012(4) Uani 1 1 d . . . . .
N2A N 0.9310(19) 0.4112(11) 0.3273(15) 0.021(4) Uani 1 1 d . . . . .
C1A C 1.091(2) 0.6796(12) 0.8464(15) 0.017(3) Uani 1 1 d . U . . .
C2A C 0.949(2) 0.6686(11) 0.7889(14) 0.017(3) Uani 1 1 d . U . . .
H2A H 0.8646 0.6981 0.8093 0.020 Uiso 1 1 calc R U . . .
C3A C 0.929(2) 0.6146(11) 0.7020(15) 0.017(3) Uani 1 1 d . U . . .
H3A H 0.8316 0.6065 0.6639 0.020 Uiso 1 1 calc R U . . .
C4A C 1.049(2) 0.5734(12) 0.6717(17) 0.016(3) Uani 1 1 d . U . . .
C5A C 1.197(2) 0.5834(12) 0.7299(15) 0.018(3) Uani 1 1 d . U . . .
H5A H 1.2812 0.5544 0.7084 0.021 Uiso 1 1 calc R U . . .
C6A C 1.215(2) 0.6366(12) 0.8185(15) 0.019(3) Uani 1 1 d . U . . .
H6A H 1.3106 0.6433 0.8598 0.023 Uiso 1 1 calc R U . . .
C7A C 1.045(2) 0.5149(12) 0.5763(15) 0.015(3) Uani 1 1 d . U . . .
C8A C 0.893(2) 0.4930(11) 0.5098(15) 0.015(3) Uani 1 1 d . U . . .
C9A C 0.813(2) 0.4450(11) 0.5957(15) 0.018(3) Uani 1 1 d . U . . .
H9A1 H 0.8089 0.4739 0.6684 0.022 Uiso 1 1 calc R U . . .
H9A2 H 0.8719 0.3980 0.6128 0.022 Uiso 1 1 calc R U . . .
C10A C 0.652(2) 0.4234(12) 0.5514(15) 0.020(3) Uani 1 1 d . U . . .
H10C H 0.6031 0.3932 0.6101 0.024 Uiso 1 1 calc R U . . .
H10D H 0.6541 0.3923 0.4806 0.024 Uiso 1 1 calc R U . . .
C11A C 0.562(2) 0.4980(12) 0.5251(15) 0.020(3) Uani 1 1 d . U . . .
H11C H 0.4557 0.4855 0.4978 0.024 Uiso 1 1 calc R U . . .
H11D H 0.5592 0.5286 0.5963 0.024 Uiso 1 1 calc R U . . .
C12A C 0.635(2) 0.5441(12) 0.4337(15) 0.020(4) Uani 1 1 d . U . . .
H12C H 0.6253 0.5160 0.3598 0.024 Uiso 1 1 calc R U . . .
H12D H 0.5809 0.5932 0.4222 0.024 Uiso 1 1 calc R U . . .
C13A C 0.865(2) 0.6176(11) 0.4093(16) 0.015(4) Uani 1 1 d . . . . .
C14A C 1.113(2) 0.6795(11) 0.3964(17) 0.020(4) Uani 1 1 d . U . . .
C15A C 1.269(2) 0.6445(12) 0.4168(17) 0.026(4) Uani 1 1 d . U . . .
H15D H 1.3463 0.6823 0.4002 0.038 Uiso 1 1 calc R U . . .
H15E H 1.2775 0.6003 0.3662 0.038 Uiso 1 1 calc R U . . .
H15F H 1.2856 0.6282 0.4973 0.038 Uiso 1 1 calc R U . . .
C16A C 1.0949(19) 0.7420(14) 0.4840(14) 0.021(4) Uani 1 1 d . U . . .
H16D H 0.9907 0.7614 0.4761 0.032 Uiso 1 1 calc R U . . .
H16E H 1.1656 0.7836 0.4707 0.032 Uiso 1 1 calc R U . . .
H16F H 1.1170 0.7216 0.5617 0.032 Uiso 1 1 calc R U . . .
C17A C 1.090(2) 0.7056(13) 0.2740(16) 0.027(4) Uani 1 1 d . U . . .
H17D H 0.9816 0.7063 0.2498 0.040 Uiso 1 1 calc R U . . .
H17E H 1.1423 0.6706 0.2246 0.040 Uiso 1 1 calc R U . . .
H17F H 1.1322 0.7569 0.2674 0.040 Uiso 1 1 calc R U . . .
C18A C 0.922(2) 0.4464(11) 0.4069(16) 0.014(3) Uani 1 1 d . 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 C1 1.891(19) . ?
O1 C7 1.21(2) . ?
O2 C13 1.20(2) . ?
O3 C13 1.35(2) . ?
O3 C14 1.52(2) . ?
N1 C13 1.39(2) . ?
N1 C8 1.47(2) . ?
N1 C12 1.50(2) . ?
N2 C18 1.14(2) . ?
C1 C2 1.34(3) . ?
C1 C6 1.39(2) . ?
C2 C3 1.38(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.42(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.38(3) . ?
C4 C7 1.52(3) . ?
C5 C6 1.41(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.53(3) . ?
C8 C18 1.48(3) . ?
C8 C9 1.55(3) . ?
C9 C10 1.54(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.54(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.50(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C14 C15 1.51(2) . ?
C14 C16 1.49(3) . ?
C14 C17 1.54(3) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
Br00 C1A 1.882(19) . ?
O1A C7A 1.25(2) . ?
O2A C13A 1.21(2) . ?
O3A C13A 1.33(2) . ?
O3A C14A 1.50(2) . ?
N1A C13A 1.39(2) . ?
N1A C8A 1.49(2) . ?
N1A C12A 1.49(2) . ?
N2A C18A 1.12(2) . ?
C1A C6A 1.38(3) . ?
C1A C2A 1.40(2) . ?
C2A C3A 1.39(3) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.35(3) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.44(3) . ?
C4A C7A 1.51(3) . ?
C5A C6A 1.39(3) . ?
C5A H5A 0.9500 . ?
C6A H6A 0.9500 . ?
C7A C8A 1.55(3) . ?
C8A C18A 1.49(3) . ?
C8A C9A 1.52(2) . ?
C9A C10A 1.52(3) . ?
C9A H9A1 0.9900 . ?
C9A H9A2 0.9900 . ?
C10A C11A 1.55(3) . ?
C10A H10C 0.9900 . ?
C10A H10D 0.9900 . ?
C11A C12A 1.52(3) . ?
C11A H11C 0.9900 . ?
C11A H11D 0.9900 . ?
C12A H12C 0.9900 . ?
C12A H12D 0.9900 . ?
C14A C17A 1.50(2) . ?
C14A C15A 1.52(3) . ?
C14A C16A 1.52(3) . ?
C15A H15D 0.9800 . ?
C15A H15E 0.9800 . ?
C15A H15F 0.9800 . ?
C16A H16D 0.9800 . ?
C16A H16E 0.9800 . ?
C16A H16F 0.9800 . ?
C17A H17D 0.9800 . ?
C17A H17E 0.9800 . ?
C17A H17F 0.9800 . ?

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
C13 O3 C14 120.8(14) . . ?
C13 N1 C8 121.0(15) . . ?
C13 N1 C12 114.4(15) . . ?
C8 N1 C12 115.4(15) . . ?
C2 C1 C6 122.0(18) . . ?
C2 C1 Br1 118.9(15) . . ?
C6 C1 Br1 119.1(15) . . ?
C1 C2 C3 120.5(19) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C2 C3 C4 119(2) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C5 C4 C3 119.3(18) . . ?
C5 C4 C7 125.3(18) . . ?
C3 C4 C7 115.4(18) . . ?
C4 C5 C6 120.1(19) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C5 118.6(19) . . ?
C1 C6 H6 120.7 . . ?
C5 C6 H6 120.7 . . ?
O1 C7 C4 120.6(17) . . ?
O1 C7 C8 118.5(18) . . ?
C4 C7 C8 120.4(17) . . ?
N1 C8 C18 106.8(15) . . ?
N1 C8 C7 117.3(17) . . ?
C18 C8 C7 108.4(16) . . ?
N1 C8 C9 108.9(15) . . ?
C18 C8 C9 110.0(17) . . ?
C7 C8 C9 105.4(15) . . ?
C10 C9 C8 114.2(14) . . ?
C10 C9 H9A 108.7 . . ?
C8 C9 H9A 108.7 . . ?
C10 C9 H9B 108.7 . . ?
C8 C9 H9B 108.7 . . ?
H9A C9 H9B 107.6 . . ?
C9 C10 C11 106.8(16) . . ?
C9 C10 H10A 110.4 . . ?
C11 C10 H10A 110.4 . . ?
C9 C10 H10B 110.4 . . ?
C11 C10 H10B 110.4 . . ?
H10A C10 H10B 108.6 . . ?
C12 C11 C10 110.7(17) . . ?
C12 C11 H11A 109.5 . . ?
C10 C11 H11A 109.5 . . ?
C12 C11 H11B 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
C11 C12 N1 111.8(14) . . ?
C11 C12 H12A 109.3 . . ?
N1 C12 H12A 109.3 . . ?
C11 C12 H12B 109.3 . . ?
N1 C12 H12B 109.3 . . ?
H12A C12 H12B 107.9 . . ?
O2 C13 O3 126.0(18) . . ?
O2 C13 N1 124.2(18) . . ?
O3 C13 N1 109.8(16) . . ?
C15 C14 O3 109.6(13) . . ?
C15 C14 C16 111.6(16) . . ?
O3 C14 C16 100.8(15) . . ?
C15 C14 C17 111.3(16) . . ?
O3 C14 C17 112.2(15) . . ?
C16 C14 C17 110.8(15) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N2 C18 C8 174(2) . . ?
C13A O3A C14A 120.1(14) . . ?
C13A N1A C8A 119.2(15) . . ?
C13A N1A C12A 116.1(15) . . ?
C8A N1A C12A 117.6(16) . . ?
C6A C1A C2A 120.7(19) . . ?
C6A C1A Br00 119.3(14) . . ?
C2A C1A Br00 120.0(15) . . ?
C3A C2A C1A 120.1(19) . . ?
C3A C2A H2A 120.0 . . ?
C1A C2A H2A 120.0 . . ?
C4A C3A C2A 119.9(19) . . ?
C4A C3A H3A 120.0 . . ?
C2A C3A H3A 120.0 . . ?
C3A C4A C5A 121.0(19) . . ?
C3A C4A C7A 125.4(19) . . ?
C5A C4A C7A 113.6(18) . . ?
C6A C5A C4A 118.6(19) . . ?
C6A C5A H5A 120.7 . . ?
C4A C5A H5A 120.7 . . ?
C5A C6A C1A 119.7(18) . . ?
C5A C6A H6A 120.2 . . ?
C1A C6A H6A 120.2 . . ?
O1A C7A C4A 123.1(18) . . ?
O1A C7A C8A 115.9(18) . . ?
C4A C7A C8A 120.5(17) . . ?
N1A C8A C18A 106.6(14) . . ?
N1A C8A C9A 111.5(15) . . ?
C18A C8A C9A 110.1(16) . . ?
N1A C8A C7A 114.8(16) . . ?
C18A C8A C7A 110.0(16) . . ?
C9A C8A C7A 103.9(14) . . ?
C8A C9A C10A 112.6(15) . . ?
C8A C9A H9A1 109.1 . . ?
C10A C9A H9A1 109.1 . . ?
C8A C9A H9A2 109.1 . . ?
C10A C9A H9A2 109.1 . . ?
H9A1 C9A H9A2 107.8 . . ?
C9A C10A C11A 108.1(17) . . ?
C9A C10A H10C 110.1 . . ?
C11A C10A H10C 110.1 . . ?
C9A C10A H10D 110.1 . . ?
C11A C10A H10D 110.1 . . ?
H10C C10A H10D 108.4 . . ?
C12A C11A C10A 110.3(16) . . ?
C12A C11A H11C 109.6 . . ?
C10A C11A H11C 109.6 . . ?
C12A C11A H11D 109.6 . . ?
C10A C11A H11D 109.6 . . ?
H11C C11A H11D 108.1 . . ?
N1A C12A C11A 111.3(15) . . ?
N1A C12A H12C 109.4 . . ?
C11A C12A H12C 109.4 . . ?
N1A C12A H12D 109.4 . . ?
C11A C12A H12D 109.4 . . ?
H12C C12A H12D 108.0 . . ?
O2A C13A O3A 126.8(18) . . ?
O2A C13A N1A 121.6(18) . . ?
O3A C13A N1A 111.6(16) . . ?
C17A C14A O3A 110.6(15) . . ?
C17A C14A C15A 109.1(17) . . ?
O3A C14A C15A 100.3(15) . . ?
C17A C14A C16A 114.0(18) . . ?
O3A C14A C16A 112.9(15) . . ?
C15A C14A C16A 109.1(16) . . ?
C14A C15A H15D 109.5 . . ?
C14A C15A H15E 109.5 . . ?
H15D C15A H15E 109.5 . . ?
C14A C15A H15F 109.5 . . ?
H15D C15A H15F 109.5 . . ?
H15E C15A H15F 109.5 . . ?
C14A C16A H16D 109.5 . . ?
C14A C16A H16E 109.5 . . ?
H16D C16A H16E 109.5 . . ?
C14A C16A H16F 109.5 . . ?
H16D C16A H16F 109.5 . . ?
H16E C16A H16F 109.5 . . ?
C14A C17A H17D 109.5 . . ?
C14A C17A H17E 109.5 . . ?
H17D C17A H17E 109.5 . . ?
C14A C17A H17F 109.5 . . ?
H17D C17A H17F 109.5 . . ?
H17E C17A H17F 109.5 . . ?
N2A C18A C8A 174(2) . . ?

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
C6 C1 C2 C3 -1(3) . . . . ?
Br1 C1 C2 C3 178.6(14) . . . . ?
C1 C2 C3 C4 0(3) . . . . ?
C2 C3 C4 C5 -1(3) . . . . ?
C2 C3 C4 C7 180.0(17) . . . . ?
C3 C4 C5 C6 2(3) . . . . ?
C7 C4 C5 C6 -179.1(18) . . . . ?
C2 C1 C6 C5 2(3) . . . . ?
Br1 C1 C6 C5 -177.6(14) . . . . ?
C4 C5 C6 C1 -3(3) . . . . ?
C5 C4 C7 O1 175.5(19) . . . . ?
C3 C4 C7 O1 -6(3) . . . . ?
C5 C4 C7 C8 -12(3) . . . . ?
C3 C4 C7 C8 166.1(17) . . . . ?
C13 N1 C8 C18 -76(2) . . . . ?
C12 N1 C8 C18 68.9(19) . . . . ?
C13 N1 C8 C7 46(3) . . . . ?
C12 N1 C8 C7 -169.4(16) . . . . ?
C13 N1 C8 C9 165.2(16) . . . . ?
C12 N1 C8 C9 -50(2) . . . . ?
O1 C7 C8 N1 -135.3(19) . . . . ?
C4 C7 C8 N1 52(2) . . . . ?
O1 C7 C8 C18 -14(2) . . . . ?
C4 C7 C8 C18 173.3(16) . . . . ?
O1 C7 C8 C9 103(2) . . . . ?
C4 C7 C8 C9 -69(2) . . . . ?
N1 C8 C9 C10 53(2) . . . . ?
C18 C8 C9 C10 -63(2) . . . . ?
C7 C8 C9 C10 179.9(17) . . . . ?
C8 C9 C10 C11 -58(2) . . . . ?
C9 C10 C11 C12 58(2) . . . . ?
C10 C11 C12 N1 -57(2) . . . . ?
C13 N1 C12 C11 -158.6(17) . . . . ?
C8 N1 C12 C11 54(2) . . . . ?
C14 O3 C13 O2 13(3) . . . . ?
C14 O3 C13 N1 -165.0(15) . . . . ?
C8 N1 C13 O2 165.5(18) . . . . ?
C12 N1 C13 O2 20(3) . . . . ?
C8 N1 C13 O3 -17(2) . . . . ?
C12 N1 C13 O3 -162.1(15) . . . . ?
C13 O3 C14 C15 -64(2) . . . . ?
C13 O3 C14 C16 178.0(15) . . . . ?
C13 O3 C14 C17 60(2) . . . . ?
C6A C1A C2A C3A -1(3) . . . . ?
Br00 C1A C2A C3A -179.1(14) . . . . ?
C1A C2A C3A C4A -1(3) . . . . ?
C2A C3A C4A C5A 1(3) . . . . ?
C2A C3A C4A C7A -177.8(18) . . . . ?
C3A C4A C5A C6A 0(3) . . . . ?
C7A C4A C5A C6A 179.3(18) . . . . ?
C4A C5A C6A C1A -2(3) . . . . ?
C2A C1A C6A C5A 2(3) . . . . ?
Br00 C1A C6A C5A -179.5(14) . . . . ?
C3A C4A C7A O1A -176(2) . . . . ?
C5A C4A C7A O1A 5(3) . . . . ?
C3A C4A C7A C8A -5(3) . . . . ?
C5A C4A C7A C8A 175.9(17) . . . . ?
C13A N1A C8A C18A -74.1(19) . . . . ?
C12A N1A C8A C18A 75.3(18) . . . . ?
C13A N1A C8A C9A 165.7(15) . . . . ?
C12A N1A C8A C9A -45(2) . . . . ?
C13A N1A C8A C7A 48(2) . . . . ?
C12A N1A C8A C7A -162.7(15) . . . . ?
O1A C7A C8A N1A -139.6(17) . . . . ?
C4A C7A C8A N1A 49(2) . . . . ?
O1A C7A C8A C18A -19(2) . . . . ?
C4A C7A C8A C18A 169.1(16) . . . . ?
O1A C7A C8A C9A 98.4(19) . . . . ?
C4A C7A C8A C9A -73(2) . . . . ?
N1A C8A C9A C10A 50(2) . . . . ?
C18A C8A C9A C10A -68(2) . . . . ?
C7A C8A C9A C10A 174.5(17) . . . . ?
C8A C9A C10A C11A -59(2) . . . . ?
C9A C10A C11A C12A 60.6(19) . . . . ?
C13A N1A C12A C11A -161.8(17) . . . . ?
C8A N1A C12A C11A 48(2) . . . . ?
C10A C11A C12A N1A -55(2) . . . . ?
C14A O3A C13A O2A 19(3) . . . . ?
C14A O3A C13A N1A -158.9(14) . . . . ?
C8A N1A C13A O2A 171.9(16) . . . . ?
C12A N1A C13A O2A 22(3) . . . . ?
C8A N1A C13A O3A -10(2) . . . . ?
C12A N1A C13A O3A -159.5(15) . . . . ?
C13A O3A C14A C17A -67(2) . . . . ?
C13A O3A C14A C15A 178.0(15) . . . . ?
C13A O3A C14A C16A 62(2) . . . . ?

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
C17A H17F O2 0.98 2.60 3.47(2) 147.9 2_755
C17A H17D O2A 0.98 2.32 2.99(2) 125.2 .
C16A H16D O2A 0.98 2.69 3.22(2) 114.6 .
C6A H6A N2 0.95 2.58 3.36(3) 139.6 1_656
C17 H17B O2 0.98 2.56 3.15(2) 118.8 .
C15 H15B O2 0.98 2.41 2.99(2) 117.6 .
C15 H15A O2A 0.98 2.47 3.34(2) 147.0 2_645
C2 H2 N2A 0.95 2.61 3.44(3) 145.9 1_455

_refine_diff_density_max         1.757
_refine_diff_density_min         -0.621
_refine_diff_density_rms         0.163

_shelxl_version_number           2014-1

