# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_1_a
_database_code_depnum_ccdc_archive 'CCDC 1507543'
_audit_update_record             
;
2016-09-30 deposited with the CCDC.
2016-11-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H13 Br F N O2'
_chemical_formula_weight         350.18

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'
F F 0.0171 0.0103 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'

_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'

_cell_length_a                   7.9939(5)
_cell_length_b                   8.0488(4)
_cell_length_c                   22.5543(13)
_cell_angle_alpha                96.579(2)
_cell_angle_beta                 96.368(2)
_cell_angle_gamma                90.008(2)
_cell_volume                     1432.60(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5344
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      26.52
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.624
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    2.884
_shelx_estimated_absorpt_T_min   0.510
_shelx_estimated_absorpt_T_max   0.570
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\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            10475
_diffrn_reflns_av_unetI/netI     0.0700
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.548
_diffrn_reflns_theta_max         25.010
_diffrn_reflns_theta_full        25.010
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.694
_diffrn_reflns_point_group_measured_fraction_full 0.694
_reflns_number_total             7048
_reflns_number_gt                6228
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.394
_reflns_Friedel_fraction_max     0.392
_reflns_Friedel_fraction_full    0.392

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0226P)²] 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 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.022(8)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         7048
_refine_ls_number_parameters     765
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0365
_refine_ls_wR_factor_ref         0.0809
_refine_ls_wR_factor_gt          0.0778
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.004
_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 0.29812(9) 0.36465(7) 0.91013(4) 0.03524(19) Uani 1 1 d . . . . .
Br2 Br 0.70574(10) 0.63235(8) 0.59657(4) 0.0473(2) Uani 1 1 d . . . . .
Br3 Br 0.16326(8) 0.54968(9) 0.40625(4) 0.0411(2) Uani 1 1 d . . . . .
Br4 Br 1.45004(8) 0.95623(9) 0.09883(4) 0.0387(2) Uani 1 1 d . . . . .
C1 C 0.2385(8) 0.5945(7) 0.9131(3) 0.0207(15) Uani 1 1 d . . . . .
C2 C 0.1156(8) 0.6468(8) 0.9487(3) 0.0251(16) Uani 1 1 d . . . . .
H2 H 0.0651 0.5719 0.9699 0.030 Uiso 1 1 calc R U . . .
C3 C 0.0683(8) 0.8116(9) 0.9525(3) 0.0292(17) Uani 1 1 d . . . . .
H3 H -0.0125 0.8489 0.9774 0.035 Uiso 1 1 calc R U . . .
C4 C 0.1394(8) 0.9216(8) 0.9200(3) 0.0263(17) Uani 1 1 d . . . . .
H4 H 0.1071 1.0329 0.9230 0.032 Uiso 1 1 calc R U . . .
C5 C 0.2589(8) 0.8666(7) 0.8828(3) 0.0233(16) Uani 1 1 d . . . . .
H5 H 0.3020 0.9400 0.8591 0.028 Uiso 1 1 calc R U . . .
C6 C 0.3162(8) 0.7020(8) 0.8802(3) 0.0202(15) Uani 1 1 d . . . . .
C7 C 0.4514(9) 0.6488(8) 0.8390(3) 0.0223(15) Uani 1 1 d . . . . .
H7 H 0.4474 0.5267 0.8299 0.027 Uiso 1 1 calc R U . . .
C8 C 0.6291(8) 0.7023(8) 0.8655(3) 0.0215(15) Uani 1 1 d . . . . .
C9 C 0.6667(8) 0.8860(7) 0.8804(3) 0.0200(14) Uani 1 1 d . . . . .
C10 C 0.6242(8) 1.0004(8) 0.9272(3) 0.0246(16) Uani 1 1 d . . . . .
H10 H 0.5600 0.9681 0.9560 0.030 Uiso 1 1 calc R U . . .
C11 C 0.6806(10) 1.1641(9) 0.9295(4) 0.037(2) Uani 1 1 d . . . . .
H11 H 0.6550 1.2422 0.9608 0.044 Uiso 1 1 calc R U . . .
C12 C 0.7735(10) 1.2141(9) 0.8866(4) 0.036(2) Uani 1 1 d . . . . .
H12 H 0.8041 1.3262 0.8883 0.044 Uiso 1 1 calc R U . . .
C13 C 0.8229(9) 1.0988(8) 0.8405(3) 0.0318(18) Uani 1 1 d . . . . .
H13 H 0.8882 1.1299 0.8119 0.038 Uiso 1 1 calc R U . . .
C14 C 0.7670(8) 0.9333(8) 0.8405(3) 0.0210(16) Uani 1 1 d . . . . .
C15 C 0.7473(9) 0.6530(8) 0.8174(3) 0.0256(17) Uani 1 1 d . . . . .
C16 C 0.6364(8) 0.4048(8) 0.5907(3) 0.0246(15) Uani 1 1 d . . . . .
C17 C 0.4892(9) 0.3576(9) 0.5532(3) 0.0337(18) Uani 1 1 d . . . . .
H17 H 0.4298 0.4358 0.5322 0.040 Uiso 1 1 calc R U . . .
C18 C 0.4335(9) 0.1973(10) 0.5477(3) 0.036(2) Uani 1 1 d . . . . .
H18 H 0.3360 0.1652 0.5226 0.043 Uiso 1 1 calc R U . . .
C19 C 0.5209(9) 0.0804(9) 0.5794(3) 0.0332(19) Uani 1 1 d . . . . .
H19 H 0.4814 -0.0295 0.5757 0.040 Uiso 1 1 calc R U . . .
C20 C 0.6673(9) 0.1278(8) 0.6166(3) 0.0268(16) Uani 1 1 d . . . . .
H20 H 0.7242 0.0501 0.6386 0.032 Uiso 1 1 calc R U . . .
C21 C 0.7297(9) 0.2910(8) 0.6213(3) 0.0206(15) Uani 1 1 d . . . . .
C22 C 0.8887(8) 0.3369(8) 0.6634(3) 0.0213(15) Uani 1 1 d . . . . .
H22 H 0.8925 0.4586 0.6738 0.026 Uiso 1 1 calc R U . . .
C23 C 1.0534(8) 0.2832(7) 0.6377(3) 0.0179(14) Uani 1 1 d . . . . .
C24 C 1.0834(8) 0.1018(8) 0.6220(3) 0.0204(15) Uani 1 1 d . . . . .
C25 C 1.0165(8) -0.0108(8) 0.5744(3) 0.0241(16) Uani 1 1 d . . . . .
H25 H 0.9351 0.0216 0.5454 0.029 Uiso 1 1 calc R U . . .
C26 C 1.0753(9) -0.1763(9) 0.5711(3) 0.0323(18) Uani 1 1 d . . . . .
H26 H 1.0327 -0.2546 0.5395 0.039 Uiso 1 1 calc R U . . .
C27 C 1.1951(10) -0.2225(9) 0.6144(4) 0.0321(19) Uani 1 1 d . . . . .
H27 H 1.2284 -0.3336 0.6120 0.038 Uiso 1 1 calc R U . . .
C28 C 1.2676(10) -0.1129(8) 0.6608(3) 0.0286(17) Uani 1 1 d . . . . .
H28 H 1.3498 -0.1459 0.6894 0.034 Uiso 1 1 calc R U . . .
C29 C 1.2114(9) 0.0528(8) 0.6628(3) 0.0212(15) Uani 1 1 d . . . . .
C30 C 1.1998(9) 0.3356(9) 0.6869(3) 0.0288(18) Uani 1 1 d . . . . .
C31 C 1.4220(10) 0.1893(9) 0.7468(3) 0.0367(19) Uani 1 1 d . . . . .
H31A H 1.4490 0.3010 0.7651 0.055 Uiso 1 1 calc R U . . .
H31B H 1.5170 0.1431 0.7284 0.055 Uiso 1 1 calc R U . . .
H31C H 1.3946 0.1215 0.7768 0.055 Uiso 1 1 calc R U . . .
C32 C 0.9310(11) 0.8005(10) 0.7577(3) 0.0372(19) Uani 1 1 d . . . . .
H32A H 0.9935 0.6986 0.7545 0.056 Uiso 1 1 calc R U . . .
H32B H 1.0074 0.8936 0.7692 0.056 Uiso 1 1 calc R U . . .
H32C H 0.8687 0.8132 0.7196 0.056 Uiso 1 1 calc R U . . .
C33 C 0.3935(8) 0.6184(8) 0.4104(3) 0.0248(15) Uani 1 1 d . . . . .
C34 C 0.4413(9) 0.7628(8) 0.4469(3) 0.0263(16) Uani 1 1 d . . . . .
H34 H 0.3630 0.8228 0.4679 0.032 Uiso 1 1 calc R U . . .
C35 C 0.6065(9) 0.8187(8) 0.4522(3) 0.0301(18) Uani 1 1 d . . . . .
H35 H 0.6396 0.9171 0.4765 0.036 Uiso 1 1 calc R U . . .
C36 C 0.7213(9) 0.7279(8) 0.4213(3) 0.0302(18) Uani 1 1 d . . . . .
H36 H 0.8327 0.7646 0.4250 0.036 Uiso 1 1 calc R U . . .
C37 C 0.6721(9) 0.5817(8) 0.3847(3) 0.0231(15) Uani 1 1 d . . . . .
H37 H 0.7510 0.5215 0.3639 0.028 Uiso 1 1 calc R U . . .
C38 C 0.5062(9) 0.5241(8) 0.3785(3) 0.0202(15) Uani 1 1 d . . . . .
C39 C 0.4574(8) 0.3658(8) 0.3362(3) 0.0208(15) Uani 1 1 d . . . . .
H39 H 0.3352 0.3647 0.3256 0.025 Uiso 1 1 calc R U . . .
C40 C 0.5068(8) 0.2018(8) 0.3623(3) 0.0200(15) Uani 1 1 d . . . . .
C41 C 0.6900(8) 0.1727(8) 0.3797(3) 0.0182(14) Uani 1 1 d . . . . .
C42 C 0.8005(8) 0.2405(8) 0.4284(3) 0.0238(16) Uani 1 1 d . . . . .
H42 H 0.7649 0.3215 0.4569 0.029 Uiso 1 1 calc R U . . .
C43 C 0.9645(9) 0.1848(8) 0.4335(3) 0.0303(18) Uani 1 1 d . . . . .
H43 H 1.0398 0.2283 0.4660 0.036 Uiso 1 1 calc R U . . .
C44 C 1.0177(9) 0.0654(9) 0.3911(3) 0.0322(19) Uani 1 1 d . . . . .
H44 H 1.1299 0.0339 0.3945 0.039 Uiso 1 1 calc R U . . .
C45 C 0.9073(9) -0.0095(9) 0.3430(3) 0.0301(17) Uani 1 1 d . . . . .
H45 H 0.9426 -0.0919 0.3149 0.036 Uiso 1 1 calc R U . . .
C46 C 0.7449(8) 0.0445(8) 0.3396(3) 0.0211(15) Uani 1 1 d . . . . .
C47 C 0.4601(9) 0.0550(8) 0.3116(3) 0.0247(16) Uani 1 1 d . . . . .
C48 C 0.6160(10) -0.1694(9) 0.2556(3) 0.0330(19) Uani 1 1 d . . . . .
H48A H 0.5056 -0.2163 0.2430 0.049 Uiso 1 1 calc R U . . .
H48B H 0.6859 -0.2511 0.2737 0.049 Uiso 1 1 calc R U . . .
H48C H 0.6643 -0.1373 0.2215 0.049 Uiso 1 1 calc R U . . .
C49 C 1.2185(8) 1.0221(8) 0.0916(3) 0.0227(15) Uani 1 1 d . . . . .
C50 C 1.1805(9) 1.1509(7) 0.0566(3) 0.0247(16) Uani 1 1 d . . . . .
H50 H 1.2641 1.2023 0.0393 0.030 Uiso 1 1 calc R U . . .
C51 C 1.0157(9) 1.2005(8) 0.0483(3) 0.0321(18) Uani 1 1 d . . . . .
H51 H 0.9865 1.2848 0.0243 0.038 Uiso 1 1 calc R U . . .
C52 C 0.8929(9) 1.1256(8) 0.0754(3) 0.0279(17) Uani 1 1 d . . . . .
H52 H 0.7815 1.1587 0.0691 0.034 Uiso 1 1 calc R U . . .
C53 C 0.9361(8) 1.0008(8) 0.1121(3) 0.0214(15) Uani 1 1 d . . . . .
H53 H 0.8533 0.9537 0.1311 0.026 Uiso 1 1 calc R U . . .
C54 C 1.1022(8) 0.9448(8) 0.1209(3) 0.0192(15) Uani 1 1 d . . . . .
C55 C 1.1442(8) 0.8120(7) 0.1620(3) 0.0192(14) Uani 1 1 d . . . . .
H55 H 1.2661 0.8149 0.1735 0.023 Uiso 1 1 calc R U . . .
C56 C 1.0920(8) 0.6321(8) 0.1358(3) 0.0186(15) Uani 1 1 d . . . . .
C57 C 0.9081(7) 0.5908(8) 0.1190(3) 0.0176(14) Uani 1 1 d . . . . .
C58 C 0.7946(8) 0.6257(8) 0.0710(3) 0.0231(15) Uani 1 1 d . . . . .
H58 H 0.8274 0.6900 0.0425 0.028 Uiso 1 1 calc R U . . .
C59 C 0.6312(8) 0.5632(8) 0.0663(3) 0.0284(18) Uani 1 1 d . . . . .
H59 H 0.5545 0.5850 0.0341 0.034 Uiso 1 1 calc R U . . .
C60 C 0.5809(9) 0.4686(9) 0.1090(4) 0.032(2) Uani 1 1 d . . . . .
H60 H 0.4696 0.4321 0.1060 0.038 Uiso 1 1 calc R U . . .
C61 C 0.6945(9) 0.4274(9) 0.1564(3) 0.0275(17) Uani 1 1 d . . . . .
H61 H 0.6618 0.3632 0.1850 0.033 Uiso 1 1 calc R U . . .
C62 C 0.8573(8) 0.4862(7) 0.1591(3) 0.0172(14) Uani 1 1 d . . . . .
C63 C 1.1411(8) 0.5169(8) 0.1856(3) 0.0220(15) Uani 1 1 d . . . . .
C64 C 0.9905(10) 0.3290(9) 0.2436(3) 0.0337(18) Uani 1 1 d . . . . .
H64A H 1.1020 0.2935 0.2566 0.050 Uiso 1 1 calc R U . . .
H64B H 0.9232 0.2336 0.2259 0.050 Uiso 1 1 calc R U . . .
H64C H 0.9406 0.3826 0.2775 0.050 Uiso 1 1 calc R U . . .
F1 F 0.6712(5) 0.6156(4) 0.91511(16) 0.0250(9) Uani 1 1 d . . . . .
F2 F 1.0657(5) 0.3731(4) 0.58831(15) 0.0248(9) Uani 1 1 d . . . . .
F3 F 0.4115(5) 0.1897(5) 0.40929(16) 0.0266(9) Uani 1 1 d . . . . .
F4 F 1.1851(5) 0.5899(4) 0.08792(16) 0.0245(9) Uani 1 1 d . . . . .
N1 N 0.8171(7) 0.7945(6) 0.8021(2) 0.0220(13) Uani 1 1 d . . . . .
N2 N 1.2788(7) 0.1928(7) 0.7014(2) 0.0229(14) Uani 1 1 d . . . . .
N3 N 0.6039(7) -0.0215(7) 0.2997(2) 0.0237(14) Uani 1 1 d . . . . .
N4 N 0.9994(7) 0.4471(7) 0.1991(2) 0.0244(14) Uani 1 1 d . . . . .
O1 O 0.4222(6) 0.7212(6) 0.78404(19) 0.0281(11) Uani 1 1 d . . . . .
H1 H 0.3859 0.6492 0.7570 0.042 Uiso 1 1 calc R U . . .
O2 O 0.8912(7) 0.2608(5) 0.71732(19) 0.0303(12) Uani 1 1 d . . . . .
H2A H 0.8570 0.3272 0.7435 0.045 Uiso 1 1 calc R U . . .
O3 O 0.5362(6) 0.3647(6) 0.28267(19) 0.0270(11) Uani 1 1 d . . . . .
H3A H 0.4747 0.4093 0.2577 0.040 Uiso 1 1 calc R U . . .
O4 O 1.0629(6) 0.8443(6) 0.21517(19) 0.0274(11) Uani 1 1 d . . . . .
H4A H 1.1279 0.8950 0.2418 0.041 Uiso 1 1 calc R U . . .
O5 O 0.7705(6) 0.5090(6) 0.7953(2) 0.0344(13) Uani 1 1 d . . . . .
O6 O 0.3184(6) 0.0221(6) 0.2884(2) 0.0343(13) Uani 1 1 d . . . . .
O7 O 1.2326(6) 0.4773(6) 0.7092(2) 0.0374(14) Uani 1 1 d . . . . .
O8 O 1.2823(6) 0.5001(6) 0.2090(2) 0.0345(12) Uani 1 1 d . . . . .


_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 1.906(6) . ?
Br2 C16 1.899(7) . ?
Br3 C33 1.911(7) . ?
Br4 C49 1.920(6) . ?
C1 C2 1.373(9) . ?
C1 C6 1.391(10) . ?
C2 C3 1.375(9) . ?
C2 H2 0.9300 . ?
C3 C4 1.374(11) . ?
C3 H3 0.9300 . ?
C4 C5 1.380(10) . ?
C4 H4 0.9300 . ?
C5 C6 1.398(9) . ?
C5 H5 0.9300 . ?
C6 C7 1.533(10) . ?
C7 O1 1.425(8) . ?
C7 C8 1.521(9) . ?
C7 H7 0.9800 . ?
C8 F1 1.395(8) . ?
C8 C9 1.501(9) . ?
C8 C15 1.535(10) . ?
C9 C14 1.355(10) . ?
C9 C10 1.391(9) . ?
C10 C11 1.386(11) . ?
C10 H10 0.9300 . ?
C11 C12 1.378(12) . ?
C11 H11 0.9300 . ?
C12 C13 1.403(11) . ?
C12 H12 0.9300 . ?
C13 C14 1.405(10) . ?
C13 H13 0.9300 . ?
C14 N1 1.420(8) . ?
C15 O5 1.231(7) . ?
C15 N1 1.364(9) . ?
C16 C21 1.379(9) . ?
C16 C17 1.396(9) . ?
C17 C18 1.352(11) . ?
C17 H17 0.9300 . ?
C18 C19 1.388(11) . ?
C18 H18 0.9300 . ?
C19 C20 1.389(9) . ?
C19 H19 0.9300 . ?
C20 C21 1.393(10) . ?
C20 H20 0.9300 . ?
C21 C22 1.519(9) . ?
C22 O2 1.422(8) . ?
C22 C23 1.538(9) . ?
C22 H22 0.9800 . ?
C23 F2 1.408(7) . ?
C23 C24 1.489(8) . ?
C23 C30 1.545(8) . ?
C24 C25 1.382(8) . ?
C24 C29 1.386(9) . ?
C25 C26 1.409(10) . ?
C25 H25 0.9300 . ?
C26 C27 1.373(11) . ?
C26 H26 0.9300 . ?
C27 C28 1.365(10) . ?
C27 H27 0.9300 . ?
C28 C29 1.404(9) . ?
C28 H28 0.9300 . ?
C29 N2 1.411(8) . ?
C30 O7 1.209(8) . ?
C30 N2 1.365(9) . ?
C31 N2 1.451(8) . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32 N1 1.430(10) . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C33 C34 1.372(9) . ?
C33 C38 1.387(10) . ?
C34 C35 1.383(10) . ?
C34 H34 0.9300 . ?
C35 C36 1.374(10) . ?
C35 H35 0.9300 . ?
C36 C37 1.388(9) . ?
C36 H36 0.9300 . ?
C37 C38 1.392(10) . ?
C37 H37 0.9300 . ?
C38 C39 1.525(8) . ?
C39 O3 1.422(8) . ?
C39 C40 1.540(9) . ?
C39 H39 0.9800 . ?
C40 F3 1.384(8) . ?
C40 C41 1.499(9) . ?
C40 C47 1.562(8) . ?
C41 C42 1.390(9) . ?
C41 C46 1.396(9) . ?
C42 C43 1.383(10) . ?
C42 H42 0.9300 . ?
C43 C44 1.379(11) . ?
C43 H43 0.9300 . ?
C44 C45 1.397(10) . ?
C44 H44 0.9300 . ?
C45 C46 1.366(10) . ?
C45 H45 0.9300 . ?
C46 N3 1.425(8) . ?
C47 O6 1.210(8) . ?
C47 N3 1.343(9) . ?
C48 N3 1.470(8) . ?
C48 H48A 0.9600 . ?
C48 H48B 0.9600 . ?
C48 H48C 0.9600 . ?
C49 C54 1.384(10) . ?
C49 C50 1.387(9) . ?
C50 C51 1.376(10) . ?
C50 H50 0.9300 . ?
C51 C52 1.385(11) . ?
C51 H51 0.9300 . ?
C52 C53 1.393(10) . ?
C52 H52 0.9300 . ?
C53 C54 1.403(9) . ?
C53 H53 0.9300 . ?
C54 C55 1.508(9) . ?
C55 O4 1.425(8) . ?
C55 C56 1.540(8) . ?
C55 H55 0.9800 . ?
C56 F4 1.389(7) . ?
C56 C57 1.504(8) . ?
C56 C63 1.555(9) . ?
C57 C58 1.387(9) . ?
C57 C62 1.395(9) . ?
C58 C59 1.388(9) . ?
C58 H58 0.9300 . ?
C59 C60 1.386(11) . ?
C59 H59 0.9300 . ?
C60 C61 1.394(10) . ?
C60 H60 0.9300 . ?
C61 C62 1.378(10) . ?
C61 H61 0.9300 . ?
C62 N4 1.429(8) . ?
C63 O8 1.206(8) . ?
C63 N4 1.344(9) . ?
C64 N4 1.466(9) . ?
C64 H64A 0.9600 . ?
C64 H64B 0.9600 . ?
C64 H64C 0.9600 . ?
O1 H1 0.8200 . ?
O2 H2A 0.8200 . ?
O3 H3A 0.8200 . ?
O4 H4A 0.8200 . ?

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
C2 C1 C6 122.3(6) . . ?
C2 C1 Br1 116.7(5) . . ?
C6 C1 Br1 120.9(5) . . ?
C1 C2 C3 119.0(7) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
C4 C3 C2 120.6(7) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 119.9(6) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 120.9(7) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C5 117.0(6) . . ?
C1 C6 C7 124.2(6) . . ?
C5 C6 C7 118.7(6) . . ?
O1 C7 C8 105.8(6) . . ?
O1 C7 C6 110.8(5) . . ?
C8 C7 C6 113.9(5) . . ?
O1 C7 H7 108.7 . . ?
C8 C7 H7 108.7 . . ?
C6 C7 H7 108.7 . . ?
F1 C8 C9 111.5(5) . . ?
F1 C8 C7 107.6(6) . . ?
C9 C8 C7 118.0(5) . . ?
F1 C8 C15 110.0(5) . . ?
C9 C8 C15 101.7(6) . . ?
C7 C8 C15 107.7(5) . . ?
C14 C9 C10 120.3(6) . . ?
C14 C9 C8 108.3(5) . . ?
C10 C9 C8 131.3(7) . . ?
C11 C10 C9 117.8(7) . . ?
C11 C10 H10 121.1 . . ?
C9 C10 H10 121.1 . . ?
C12 C11 C10 121.7(7) . . ?
C12 C11 H11 119.2 . . ?
C10 C11 H11 119.2 . . ?
C11 C12 C13 121.1(7) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
C14 C13 C12 115.5(8) . . ?
C14 C13 H13 122.2 . . ?
C12 C13 H13 122.2 . . ?
C9 C14 C13 123.4(6) . . ?
C9 C14 N1 111.9(6) . . ?
C13 C14 N1 124.6(7) . . ?
O5 C15 N1 126.0(7) . . ?
O5 C15 C8 125.0(7) . . ?
N1 C15 C8 109.0(5) . . ?
C21 C16 C17 121.7(6) . . ?
C21 C16 Br2 121.2(5) . . ?
C17 C16 Br2 117.1(5) . . ?
C18 C17 C16 119.5(7) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C17 C18 C19 120.5(6) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C18 C19 C20 119.8(7) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 H19 120.1 . . ?
C19 C20 C21 120.5(7) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 H20 119.7 . . ?
C16 C21 C20 117.9(6) . . ?
C16 C21 C22 123.6(6) . . ?
C20 C21 C22 118.3(6) . . ?
O2 C22 C21 111.6(6) . . ?
O2 C22 C23 105.1(5) . . ?
C21 C22 C23 114.7(5) . . ?
O2 C22 H22 108.4 . . ?
C21 C22 H22 108.4 . . ?
C23 C22 H22 108.4 . . ?
F2 C23 C24 111.3(5) . . ?
F2 C23 C22 106.8(5) . . ?
C24 C23 C22 118.9(6) . . ?
F2 C23 C30 109.4(5) . . ?
C24 C23 C30 102.8(5) . . ?
C22 C23 C30 107.4(5) . . ?
C25 C24 C29 119.8(6) . . ?
C25 C24 C23 131.6(6) . . ?
C29 C24 C23 108.4(5) . . ?
C24 C25 C26 118.0(6) . . ?
C24 C25 H25 121.0 . . ?
C26 C25 H25 121.0 . . ?
C27 C26 C25 120.4(6) . . ?
C27 C26 H26 119.8 . . ?
C25 C26 H26 119.8 . . ?
C28 C27 C26 122.9(7) . . ?
C28 C27 H27 118.5 . . ?
C26 C27 H27 118.5 . . ?
C27 C28 C29 116.3(6) . . ?
C27 C28 H28 121.9 . . ?
C29 C28 H28 121.9 . . ?
C24 C29 C28 122.4(6) . . ?
C24 C29 N2 110.1(5) . . ?
C28 C29 N2 127.4(6) . . ?
O7 C30 N2 127.4(6) . . ?
O7 C30 C23 125.3(6) . . ?
N2 C30 C23 107.3(5) . . ?
N2 C31 H31A 109.5 . . ?
N2 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
N2 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
N1 C32 H32A 109.5 . . ?
N1 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
N1 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C34 C33 C38 122.2(7) . . ?
C34 C33 Br3 116.9(5) . . ?
C38 C33 Br3 120.9(5) . . ?
C33 C34 C35 119.8(6) . . ?
C33 C34 H34 120.1 . . ?
C35 C34 H34 120.1 . . ?
C36 C35 C34 119.5(6) . . ?
C36 C35 H35 120.3 . . ?
C34 C35 H35 120.3 . . ?
C35 C36 C37 120.4(7) . . ?
C35 C36 H36 119.8 . . ?
C37 C36 H36 119.8 . . ?
C36 C37 C38 120.9(7) . . ?
C36 C37 H37 119.6 . . ?
C38 C37 H37 119.6 . . ?
C33 C38 C37 117.3(6) . . ?
C33 C38 C39 123.9(6) . . ?
C37 C38 C39 118.8(6) . . ?
O3 C39 C38 110.4(6) . . ?
O3 C39 C40 106.5(5) . . ?
C38 C39 C40 114.5(5) . . ?
O3 C39 H39 108.4 . . ?
C38 C39 H39 108.4 . . ?
C40 C39 H39 108.4 . . ?
F3 C40 C41 112.2(5) . . ?
F3 C40 C39 107.0(5) . . ?
C41 C40 C39 117.9(6) . . ?
F3 C40 C47 109.9(5) . . ?
C41 C40 C47 102.2(5) . . ?
C39 C40 C47 107.4(5) . . ?
C42 C41 C46 119.2(6) . . ?
C42 C41 C40 131.6(6) . . ?
C46 C41 C40 109.0(5) . . ?
C43 C42 C41 118.6(6) . . ?
C43 C42 H42 120.7 . . ?
C41 C42 H42 120.7 . . ?
C44 C43 C42 120.7(6) . . ?
C44 C43 H43 119.6 . . ?
C42 C43 H43 119.6 . . ?
C43 C44 C45 121.7(7) . . ?
C43 C44 H44 119.1 . . ?
C45 C44 H44 119.1 . . ?
C46 C45 C44 116.5(7) . . ?
C46 C45 H45 121.8 . . ?
C44 C45 H45 121.8 . . ?
C45 C46 C41 123.0(6) . . ?
C45 C46 N3 128.2(6) . . ?
C41 C46 N3 108.7(6) . . ?
O6 C47 N3 128.5(6) . . ?
O6 C47 C40 124.2(6) . . ?
N3 C47 C40 107.3(5) . . ?
N3 C48 H48A 109.5 . . ?
N3 C48 H48B 109.5 . . ?
H48A C48 H48B 109.5 . . ?
N3 C48 H48C 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
C54 C49 C50 124.1(6) . . ?
C54 C49 Br4 120.5(5) . . ?
C50 C49 Br4 115.3(5) . . ?
C51 C50 C49 118.1(7) . . ?
C51 C50 H50 120.9 . . ?
C49 C50 H50 120.9 . . ?
C50 C51 C52 120.4(7) . . ?
C50 C51 H51 119.8 . . ?
C52 C51 H51 119.8 . . ?
C51 C52 C53 120.1(7) . . ?
C51 C52 H52 119.9 . . ?
C53 C52 H52 119.9 . . ?
C52 C53 C54 121.2(7) . . ?
C52 C53 H53 119.4 . . ?
C54 C53 H53 119.4 . . ?
C49 C54 C53 116.0(6) . . ?
C49 C54 C55 124.5(6) . . ?
C53 C54 C55 119.4(6) . . ?
O4 C55 C54 110.7(5) . . ?
O4 C55 C56 105.4(5) . . ?
C54 C55 C56 115.7(5) . . ?
O4 C55 H55 108.3 . . ?
C54 C55 H55 108.3 . . ?
C56 C55 H55 108.3 . . ?
F4 C56 C57 111.7(5) . . ?
F4 C56 C55 106.7(5) . . ?
C57 C56 C55 118.9(5) . . ?
F4 C56 C63 109.6(5) . . ?
C57 C56 C63 102.2(6) . . ?
C55 C56 C63 107.4(5) . . ?
C58 C57 C62 119.0(6) . . ?
C58 C57 C56 132.4(7) . . ?
C62 C57 C56 108.4(5) . . ?
C57 C58 C59 119.0(7) . . ?
C57 C58 H58 120.5 . . ?
C59 C58 H58 120.5 . . ?
C60 C59 C58 120.8(7) . . ?
C60 C59 H59 119.6 . . ?
C58 C59 H59 119.6 . . ?
C59 C60 C61 121.1(7) . . ?
C59 C60 H60 119.5 . . ?
C61 C60 H60 119.5 . . ?
C62 C61 C60 117.0(7) . . ?
C62 C61 H61 121.5 . . ?
C60 C61 H61 121.5 . . ?
C61 C62 C57 122.9(6) . . ?
C61 C62 N4 127.5(6) . . ?
C57 C62 N4 109.5(5) . . ?
O8 C63 N4 127.0(7) . . ?
O8 C63 C56 124.8(6) . . ?
N4 C63 C56 108.1(5) . . ?
N4 C64 H64A 109.5 . . ?
N4 C64 H64B 109.5 . . ?
H64A C64 H64B 109.5 . . ?
N4 C64 H64C 109.5 . . ?
H64A C64 H64C 109.5 . . ?
H64B C64 H64C 109.5 . . ?
C15 N1 C14 108.4(6) . . ?
C15 N1 C32 125.7(6) . . ?
C14 N1 C32 125.8(6) . . ?
C30 N2 C29 110.7(5) . . ?
C30 N2 C31 124.1(6) . . ?
C29 N2 C31 125.0(6) . . ?
C47 N3 C46 112.2(5) . . ?
C47 N3 C48 125.1(5) . . ?
C46 N3 C48 122.3(6) . . ?
C63 N4 C62 111.1(6) . . ?
C63 N4 C64 125.6(6) . . ?
C62 N4 C64 123.0(6) . . ?
C7 O1 H1 109.5 . . ?
C22 O2 H2A 109.5 . . ?
C39 O3 H3A 109.5 . . ?
C55 O4 H4A 109.5 . . ?

_refine_diff_density_max         0.512
_refine_diff_density_min         -0.418
_refine_diff_density_rms         0.081



