# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_a263
_database_code_depnum_ccdc_archive 'CCDC 1413018'
_audit_update_record             
;
2015-07-15 deposited with the CCDC.
2016-11-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H20 Br4 Cl2 F6'
_chemical_formula_weight         908.98

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'
H H 0.0000 0.0000 '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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.3184(2)
_cell_length_b                   13.4865(3)
_cell_length_c                   17.4149(4)
_cell_angle_alpha                101.672(2)
_cell_angle_beta                 94.139(2)
_cell_angle_gamma                101.918(2)
_cell_volume                     1635.33(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    17222
_cell_measurement_theta_min      3.4020
_cell_measurement_theta_max      76.1020

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.846
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             880
_exptl_absorpt_coefficient_mu    8.018
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.22148
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3829
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            33701
_diffrn_reflns_av_R_equivalents  0.0826
_diffrn_reflns_av_sigmaI/netI    0.0433
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.44
_diffrn_reflns_theta_max         70.99
_reflns_number_total             6300
_reflns_number_gt                5416
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?

_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_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)+(0.1373P)²+0.5435P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6300
_refine_ls_number_parameters     397
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0454
_refine_ls_wR_factor_ref         0.1869
_refine_ls_wR_factor_gt          0.1445
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.001
_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
Br1A Br 0.27004(7) 0.88560(4) -0.07986(3) 0.06163(19) Uani 1 1 d . . .
Br2A Br 0.16260(7) 0.98509(4) 0.09630(3) 0.06149(18) Uani 1 1 d . . .
Cl1A Cl 0.8421(2) 0.54188(11) -0.05715(10) 0.0803(4) Uani 1 1 d . . .
F2A F 0.3001(6) 0.7521(3) 0.2477(2) 0.0863(9) Uani 1 1 d . . .
F1A F 0.1299(6) 0.7131(2) 0.1362(2) 0.0935(11) Uani 1 1 d . . .
F3A F 0.1113(6) 0.8447(3) 0.2239(3) 0.0945(11) Uani 1 1 d . . .
C12A C 0.7054(8) 0.9472(5) 0.2266(3) 0.0760(14) Uani 1 1 d . . .
H12A H 0.7496 0.8944 0.1958 0.091 Uiso 1 1 calc R . .
C8A C 0.7018(7) 0.6301(3) -0.0360(2) 0.0539(9) Uani 1 1 d . . .
C3A C 0.3162(6) 0.8870(3) 0.0837(2) 0.0483(8) Uani 1 1 d . . .
C10A C 0.3975(6) 0.6668(3) -0.0351(3) 0.0532(9) Uani 1 1 d . . .
H10A H 0.2675 0.6443 -0.0456 0.064 Uiso 1 1 calc R . .
C4A C 0.3578(6) 0.8471(3) 0.0131(2) 0.0474(8) Uani 1 1 d . . .
C5A C 0.4768(6) 0.7713(3) -0.0035(2) 0.0459(8) Uani 1 1 d . . .
C6A C 0.6714(6) 0.8038(3) 0.0116(3) 0.0541(9) Uani 1 1 d . . .
H6A H 0.7261 0.8736 0.0327 0.065 Uiso 1 1 calc R . .
C2A C 0.3886(6) 0.8561(3) 0.1573(2) 0.0510(9) Uani 1 1 d . . .
H2A H 0.4689 0.8084 0.1391 0.061 Uiso 1 1 calc R . .
C11A C 0.5154(6) 0.9451(3) 0.2187(2) 0.0532(9) Uani 1 1 d . . .
C9A C 0.5085(7) 0.5963(3) -0.0511(3) 0.0559(9) Uani 1 1 d . . .
H9A H 0.4541 0.5264 -0.0720 0.067 Uiso 1 1 calc R . .
C1A C 0.2311(8) 0.7926(3) 0.1919(3) 0.0635(11) Uani 1 1 d . . .
C7A C 0.7845(6) 0.7340(3) -0.0044(3) 0.0583(10) Uani 1 1 d . . .
H7A H 0.9147 0.7563 0.0060 0.070 Uiso 1 1 calc R . .
C16A C 0.4522(8) 1.0241(4) 0.2660(3) 0.0665(11) Uani 1 1 d . . .
H16A H 0.3247 1.0239 0.2618 0.080 Uiso 1 1 calc R . .
C15A C 0.5788(11) 1.1040(4) 0.3201(4) 0.0857(17) Uani 1 1 d . . .
H15A H 0.5351 1.1563 0.3518 0.103 Uiso 1 1 calc R . .
C13A C 0.8316(9) 1.0272(7) 0.2798(4) 0.099(2) Uani 1 1 d . . .
H13A H 0.9593 1.0278 0.2841 0.118 Uiso 1 1 calc R . .
C14A C 0.7678(11) 1.1055(6) 0.3264(4) 0.097(2) Uani 1 1 d . . .
H14A H 0.8521 1.1590 0.3619 0.116 Uiso 1 1 calc R . .
Br2 Br 0.84500(8) 0.49282(4) 0.40291(3) 0.0688(2) Uani 1 1 d . . .
Br1 Br 0.73489(9) 0.64733(5) 0.55802(3) 0.0794(2) Uani 1 1 d . . .
Cl1 Cl 0.1351(2) 0.93704(12) 0.43257(11) 0.0894(4) Uani 1 1 d . . .
F2 F 0.6474(6) 0.6275(3) 0.19042(18) 0.0881(10) Uani 1 1 d . . .
F1 F 0.8443(6) 0.7021(3) 0.2914(2) 0.1052(14) Uani 1 1 d . . .
F3 F 0.8418(6) 0.5473(3) 0.2302(3) 0.0985(12) Uani 1 1 d . . .
C3 C 0.6796(6) 0.5807(3) 0.3908(2) 0.0527(9) Uani 1 1 d . . .
C10 C 0.5836(7) 0.8154(3) 0.4338(3) 0.0607(10) Uani 1 1 d . . .
H10 H 0.7099 0.8355 0.4272 0.073 Uiso 1 1 calc R . .
C11 C 0.4588(6) 0.4676(3) 0.2723(2) 0.0497(8) Uani 1 1 d . . .
C4 C 0.6395(6) 0.6444(3) 0.4529(2) 0.0531(9) Uani 1 1 d . . .
C5 C 0.5148(6) 0.7175(3) 0.4485(2) 0.0519(9) Uani 1 1 d . . .
C12 C 0.2678(7) 0.4613(4) 0.2709(3) 0.0633(11) Uani 1 1 d . . .
H12 H 0.2245 0.5213 0.2877 0.076 Uiso 1 1 calc R . .
C8 C 0.2820(6) 0.8526(4) 0.4383(3) 0.0600(10) Uani 1 1 d . . .
C2 C 0.5910(6) 0.5734(3) 0.3080(2) 0.0508(9) Uani 1 1 d . . .
H2 H 0.5096 0.6231 0.3141 0.061 Uiso 1 1 calc R . .
C16 C 0.5207(7) 0.3781(3) 0.2450(3) 0.0602(10) Uani 1 1 d . . .
H16 H 0.6488 0.3809 0.2452 0.072 Uiso 1 1 calc R . .
C13 C 0.1402(8) 0.3673(5) 0.2449(4) 0.0783(15) Uani 1 1 d . . .
H13 H 0.0123 0.3642 0.2456 0.094 Uiso 1 1 calc R . .
C6 C 0.3272(7) 0.6890(4) 0.4584(3) 0.0657(11) Uani 1 1 d . . .
H6 H 0.2792 0.6242 0.4685 0.079 Uiso 1 1 calc R . .
C7 C 0.2108(8) 0.7562(4) 0.4533(3) 0.0714(13) Uani 1 1 d . . .
H7 H 0.0844 0.7366 0.4599 0.086 Uiso 1 1 calc R . .
C9 C 0.4690(7) 0.8823(4) 0.4289(3) 0.0664(12) Uani 1 1 d . . .
H9 H 0.5169 0.9475 0.4192 0.080 Uiso 1 1 calc R . .
C15 C 0.3905(8) 0.2835(4) 0.2173(3) 0.0686(13) Uani 1 1 d . . .
H15 H 0.4327 0.2237 0.1983 0.082 Uiso 1 1 calc R . .
C1 C 0.7340(8) 0.6121(4) 0.2558(3) 0.0679(12) Uani 1 1 d . . .
C14 C 0.2018(8) 0.2776(4) 0.2176(3) 0.0718(13) Uani 1 1 d . . .
H14 H 0.1160 0.2142 0.1998 0.086 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
Br1A C4A 1.905(4) . ?
Br2A C3A 1.896(4) . ?
Cl1A C8A 1.728(4) . ?
F2A C1A 1.326(6) . ?
F1A C1A 1.336(6) . ?
F3A C1A 1.319(6) . ?
C12A C11A 1.381(7) . ?
C12A C13A 1.392(9) . ?
C12A H12A 0.9300 . ?
C8A C9A 1.382(7) . ?
C8A C7A 1.387(6) . ?
C3A C4A 1.323(6) . ?
C3A C2A 1.518(6) . ?
C10A C9A 1.374(6) . ?
C10A C5A 1.388(5) . ?
C10A H10A 0.9300 . ?
C4A C5A 1.474(6) . ?
C5A C6A 1.390(6) . ?
C6A C7A 1.377(6) . ?
C6A H6A 0.9300 . ?
C2A C11A 1.524(6) . ?
C2A C1A 1.525(6) . ?
C2A H2A 0.9800 . ?
C11A C16A 1.390(6) . ?
C9A H9A 0.9300 . ?
C7A H7A 0.9300 . ?
C16A C15A 1.399(7) . ?
C16A H16A 0.9300 . ?
C15A C14A 1.375(11) . ?
C15A H15A 0.9300 . ?
C13A C14A 1.380(11) . ?
C13A H13A 0.9300 . ?
C14A H14A 0.9300 . ?
Br2 C3 1.890(4) . ?
Br1 C4 1.902(4) . ?
Cl1 C8 1.732(5) . ?
F2 C1 1.337(6) . ?
F1 C1 1.315(6) . ?
F3 C1 1.328(7) . ?
C3 C4 1.330(6) . ?
C3 C2 1.512(6) . ?
C10 C9 1.363(7) . ?
C10 C5 1.395(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.381(7) . ?
C11 C16 1.383(6) . ?
C11 C2 1.531(5) . ?
C4 C5 1.484(6) . ?
C5 C6 1.380(7) . ?
C12 C13 1.379(7) . ?
C12 H12 0.9300 . ?
C8 C9 1.375(7) . ?
C8 C7 1.382(7) . ?
C2 C1 1.517(7) . ?
C2 H2 0.9800 . ?
C16 C15 1.398(7) . ?
C16 H16 0.9300 . ?
C13 C14 1.384(8) . ?
C13 H13 0.9300 . ?
C6 C7 1.376(8) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C9 H9 0.9300 . ?
C15 C14 1.367(8) . ?
C15 H15 0.9300 . ?
C14 H14 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
C11A C12A C13A 121.0(6) . . ?
C11A C12A H12A 119.5 . . ?
C13A C12A H12A 119.5 . . ?
C9A C8A C7A 120.8(4) . . ?
C9A C8A Cl1A 119.6(3) . . ?
C7A C8A Cl1A 119.6(4) . . ?
C4A C3A C2A 121.6(4) . . ?
C4A C3A Br2A 120.8(3) . . ?
C2A C3A Br2A 117.7(3) . . ?
C9A C10A C5A 120.9(4) . . ?
C9A C10A H10A 119.6 . . ?
C5A C10A H10A 119.6 . . ?
C3A C4A C5A 125.4(4) . . ?
C3A C4A Br1A 122.2(3) . . ?
C5A C4A Br1A 112.4(3) . . ?
C10A C5A C6A 118.9(4) . . ?
C10A C5A C4A 120.9(4) . . ?
C6A C5A C4A 120.2(3) . . ?
C7A C6A C5A 120.9(4) . . ?
C7A C6A H6A 119.6 . . ?
C5A C6A H6A 119.6 . . ?
C3A C2A C11A 114.6(3) . . ?
C3A C2A C1A 112.0(4) . . ?
C11A C2A C1A 113.2(4) . . ?
C3A C2A H2A 105.3 . . ?
C11A C2A H2A 105.3 . . ?
C1A C2A H2A 105.3 . . ?
C12A C11A C16A 118.5(5) . . ?
C12A C11A C2A 117.3(4) . . ?
C16A C11A C2A 124.2(4) . . ?
C10A C9A C8A 119.5(4) . . ?
C10A C9A H9A 120.3 . . ?
C8A C9A H9A 120.3 . . ?
F3A C1A F2A 106.4(4) . . ?
F3A C1A F1A 106.6(5) . . ?
F2A C1A F1A 106.8(4) . . ?
F3A C1A C2A 115.1(4) . . ?
F2A C1A C2A 111.0(4) . . ?
F1A C1A C2A 110.6(4) . . ?
C6A C7A C8A 119.1(4) . . ?
C6A C7A H7A 120.4 . . ?
C8A C7A H7A 120.4 . . ?
C11A C16A C15A 120.5(5) . . ?
C11A C16A H16A 119.7 . . ?
C15A C16A H16A 119.7 . . ?
C14A C15A C16A 120.2(6) . . ?
C14A C15A H15A 119.9 . . ?
C16A C15A H15A 119.9 . . ?
C14A C13A C12A 120.1(6) . . ?
C14A C13A H13A 119.9 . . ?
C12A C13A H13A 119.9 . . ?
C15A C14A C13A 119.7(6) . . ?
C15A C14A H14A 120.2 . . ?
C13A C14A H14A 120.2 . . ?
C4 C3 C2 121.5(4) . . ?
C4 C3 Br2 121.1(3) . . ?
C2 C3 Br2 117.3(3) . . ?
C9 C10 C5 121.1(5) . . ?
C9 C10 H10 119.4 . . ?
C5 C10 H10 119.4 . . ?
C12 C11 C16 118.8(4) . . ?
C12 C11 C2 117.6(4) . . ?
C16 C11 C2 123.5(4) . . ?
C3 C4 C5 124.6(4) . . ?
C3 C4 Br1 122.2(4) . . ?
C5 C4 Br1 113.2(3) . . ?
C6 C5 C10 118.7(4) . . ?
C6 C5 C4 120.3(4) . . ?
C10 C5 C4 121.0(4) . . ?
C13 C12 C11 121.0(5) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C9 C8 C7 120.4(5) . . ?
C9 C8 Cl1 120.0(4) . . ?
C7 C8 Cl1 119.6(4) . . ?
C3 C2 C1 112.4(4) . . ?
C3 C2 C11 112.8(3) . . ?
C1 C2 C11 115.3(4) . . ?
C3 C2 H2 105.1 . . ?
C1 C2 H2 105.1 . . ?
C11 C2 H2 105.1 . . ?
C11 C16 C15 119.9(5) . . ?
C11 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C12 C13 C14 120.3(5) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C7 C6 C5 120.4(5) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C6 C7 C8 119.9(5) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
C10 C9 C8 119.5(5) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C14 C15 C16 120.9(5) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
F1 C1 F3 108.2(5) . . ?
F1 C1 F2 106.3(4) . . ?
F3 C1 F2 105.1(4) . . ?
F1 C1 C2 111.4(4) . . ?
F3 C1 C2 115.0(4) . . ?
F2 C1 C2 110.4(5) . . ?
C15 C14 C13 119.1(5) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?

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
C2A C3A C4A C5A -0.7(6) . . . . ?
Br2A C3A C4A C5A 179.4(3) . . . . ?
C2A C3A C4A Br1A -179.5(3) . . . . ?
Br2A C3A C4A Br1A 0.6(5) . . . . ?
C9A C10A C5A C6A 0.2(6) . . . . ?
C9A C10A C5A C4A 179.5(4) . . . . ?
C3A C4A C5A C10A 102.9(5) . . . . ?
Br1A C4A C5A C10A -78.2(4) . . . . ?
C3A C4A C5A C6A -77.9(5) . . . . ?
Br1A C4A C5A C6A 101.0(4) . . . . ?
C10A C5A C6A C7A -0.1(7) . . . . ?
C4A C5A C6A C7A -179.3(4) . . . . ?
C4A C3A C2A C11A 118.2(4) . . . . ?
Br2A C3A C2A C11A -61.9(4) . . . . ?
C4A C3A C2A C1A -111.1(4) . . . . ?
Br2A C3A C2A C1A 68.8(4) . . . . ?
C13A C12A C11A C16A -0.9(9) . . . . ?
C13A C12A C11A C2A 178.4(6) . . . . ?
C3A C2A C11A C12A -106.8(5) . . . . ?
C1A C2A C11A C12A 123.1(5) . . . . ?
C3A C2A C11A C16A 72.5(6) . . . . ?
C1A C2A C11A C16A -57.7(6) . . . . ?
C5A C10A C9A C8A -0.4(7) . . . . ?
C7A C8A C9A C10A 0.5(7) . . . . ?
Cl1A C8A C9A C10A -179.2(3) . . . . ?
C3A C2A C1A F3A -69.4(5) . . . . ?
C11A C2A C1A F3A 62.0(6) . . . . ?
C3A C2A C1A F2A 169.7(4) . . . . ?
C11A C2A C1A F2A -58.9(5) . . . . ?
C3A C2A C1A F1A 51.4(5) . . . . ?
C11A C2A C1A F1A -177.2(4) . . . . ?
C5A C6A C7A C8A 0.2(7) . . . . ?
C9A C8A C7A C6A -0.3(7) . . . . ?
Cl1A C8A C7A C6A 179.4(4) . . . . ?
C12A C11A C16A C15A 0.3(8) . . . . ?
C2A C11A C16A C15A -178.9(5) . . . . ?
C11A C16A C15A C14A 0.5(9) . . . . ?
C11A C12A C13A C14A 0.6(11) . . . . ?
C16A C15A C14A C13A -0.7(11) . . . . ?
C12A C13A C14A C15A 0.2(12) . . . . ?
C2 C3 C4 C5 -3.1(6) . . . . ?
Br2 C3 C4 C5 178.6(3) . . . . ?
C2 C3 C4 Br1 175.3(3) . . . . ?
Br2 C3 C4 Br1 -3.0(5) . . . . ?
C9 C10 C5 C6 -0.2(7) . . . . ?
C9 C10 C5 C4 179.3(4) . . . . ?
C3 C4 C5 C6 95.2(6) . . . . ?
Br1 C4 C5 C6 -83.3(4) . . . . ?
C3 C4 C5 C10 -84.2(6) . . . . ?
Br1 C4 C5 C10 97.2(4) . . . . ?
C16 C11 C12 C13 1.8(7) . . . . ?
C2 C11 C12 C13 -175.3(5) . . . . ?
C4 C3 C2 C1 114.3(5) . . . . ?
Br2 C3 C2 C1 -67.3(4) . . . . ?
C4 C3 C2 C11 -113.4(4) . . . . ?
Br2 C3 C2 C11 65.0(4) . . . . ?
C12 C11 C2 C3 102.3(5) . . . . ?
C16 C11 C2 C3 -74.6(5) . . . . ?
C12 C11 C2 C1 -126.8(5) . . . . ?
C16 C11 C2 C1 56.3(6) . . . . ?
C12 C11 C16 C15 -0.4(7) . . . . ?
C2 C11 C16 C15 176.4(4) . . . . ?
C11 C12 C13 C14 -1.7(9) . . . . ?
C10 C5 C6 C7 0.4(7) . . . . ?
C4 C5 C6 C7 -179.1(5) . . . . ?
C5 C6 C7 C8 -0.1(8) . . . . ?
C9 C8 C7 C6 -0.4(8) . . . . ?
Cl1 C8 C7 C6 -179.6(4) . . . . ?
C5 C10 C9 C8 -0.3(7) . . . . ?
C7 C8 C9 C10 0.6(7) . . . . ?
Cl1 C8 C9 C10 179.7(4) . . . . ?
C11 C16 C15 C14 -0.9(8) . . . . ?
C3 C2 C1 F1 -47.6(6) . . . . ?
C11 C2 C1 F1 -178.7(4) . . . . ?
C3 C2 C1 F3 75.9(5) . . . . ?
C11 C2 C1 F3 -55.2(6) . . . . ?
C3 C2 C1 F2 -165.4(4) . . . . ?
C11 C2 C1 F2 63.5(5) . . . . ?
C16 C15 C14 C13 1.0(8) . . . . ?
C12 C13 C14 C15 0.3(9) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        70.99
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.918
_refine_diff_density_min         -1.204
_refine_diff_density_rms         0.200
####################################################################### 
# 
# 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_a274
_database_code_depnum_ccdc_archive 'CCDC 1413019'
_audit_update_record             
;
2015-07-15 deposited with the CCDC.
2016-11-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H20 Br F3 O'
_chemical_formula_weight         413.27

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'
H H 0.0000 0.0000 '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'
F F 0.0727 0.0534 '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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.8481(5)
_cell_length_b                   10.5581(7)
_cell_length_c                   12.2042(10)
_cell_angle_alpha                75.472(6)
_cell_angle_beta                 72.741(6)
_cell_angle_gamma                72.301(6)
_cell_volume                     905.55(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5104
_cell_measurement_theta_min      3.8600
_cell_measurement_theta_max      76.0720

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.516
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             420
_exptl_absorpt_coefficient_mu    3.403
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.64613
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3829
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9514
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_sigmaI/netI    0.0249
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.85
_diffrn_reflns_theta_max         72.49
_reflns_number_total             3568
_reflns_number_gt                3280
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?

_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_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)+(0.0672P)²+0.3068P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3568
_refine_ls_number_parameters     230
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0388
_refine_ls_wR_factor_ref         0.1098
_refine_ls_wR_factor_gt          0.1066
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.003
_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 0.50652(4) 0.58352(3) 0.72935(3) 0.06491(13) Uani 1 1 d . . .
C2 C 0.7205(3) 0.6372(2) 0.73792(19) 0.0427(4) Uani 1 1 d . . .
H2 H 0.8040 0.5604 0.7750 0.051 Uiso 1 1 calc R . .
F3 F 1.0960(2) 0.6670(2) 0.66928(17) 0.0772(5) Uani 1 1 d . . .
F1 F 1.1195(2) 0.6738(2) 0.48891(16) 0.0783(5) Uani 1 1 d . . .
C9 C 0.7532(3) 0.8432(2) 0.60322(18) 0.0392(4) Uani 1 1 d . . .
C6 C 0.5789(3) 1.1114(2) 0.6250(2) 0.0473(5) Uani 1 1 d . . .
C3 C 0.6529(3) 0.7550(2) 0.80712(18) 0.0413(4) Uani 1 1 d . . .
H3 H 0.5255 0.7584 0.8514 0.050 Uiso 1 1 calc R . .
C14 C 0.7703(3) 0.7394(2) 0.89171(17) 0.0419(4) Uani 1 1 d . . .
C8 C 0.7680(3) 0.9425(2) 0.50341(19) 0.0446(4) Uani 1 1 d . . .
F2 F 1.0708(2) 0.49852(17) 0.61346(18) 0.0770(5) Uani 1 1 d . . .
O1 O 1.0717(3) 0.6829(2) 1.13651(17) 0.0675(5) Uani 1 1 d . . .
C4 C 0.6544(3) 0.8776(2) 0.71132(17) 0.0398(4) Uani 1 1 d . . .
C7 C 0.6786(3) 1.0750(2) 0.5181(2) 0.0495(5) Uani 1 1 d . . .
H7 H 0.6861 1.1429 0.4527 0.059 Uiso 1 1 calc R . .
C1 C 0.8205(3) 0.6908(2) 0.61315(18) 0.0421(4) Uani 1 1 d . . .
H1 H 0.7789 0.6625 0.5570 0.050 Uiso 1 1 calc R . .
C15 C 0.7528(3) 0.6447(2) 0.99418(19) 0.0468(5) Uani 1 1 d . . .
H15 H 0.6701 0.5918 1.0097 0.056 Uiso 1 1 calc R . .
C5 C 0.5656(3) 1.0108(2) 0.72497(19) 0.0451(5) Uani 1 1 d . . .
C19 C 0.8943(3) 0.8168(2) 0.8715(2) 0.0511(5) Uani 1 1 d . . .
H19 H 0.9079 0.8809 0.8037 0.061 Uiso 1 1 calc R . .
C17 C 0.9790(3) 0.7062(2) 1.05171(19) 0.0485(5) Uani 1 1 d . . .
C10 C 1.0266(3) 0.6341(3) 0.5963(2) 0.0535(5) Uani 1 1 d . . .
C13 C 0.4553(4) 1.0432(3) 0.8431(2) 0.0640(7) Uani 1 1 d . . .
H13A H 0.4935 1.1133 0.8596 0.096 Uiso 1 1 calc R . .
H13B H 0.4755 0.9639 0.9015 0.096 Uiso 1 1 calc R . .
H13C H 0.3268 1.0733 0.8435 0.096 Uiso 1 1 calc R . .
C16 C 0.8558(4) 0.6279(2) 1.07313(19) 0.0513(5) Uani 1 1 d . . .
H16 H 0.8423 0.5637 1.1409 0.062 Uiso 1 1 calc R . .
C18 C 0.9991(4) 0.8008(2) 0.9505(2) 0.0530(5) Uani 1 1 d . . .
H18 H 1.0821 0.8535 0.9353 0.064 Uiso 1 1 calc R . .
C11 C 0.8703(4) 0.9134(3) 0.3831(2) 0.0599(6) Uani 1 1 d . . .
H11A H 0.9966 0.9152 0.3694 0.090 Uiso 1 1 calc R . .
H11B H 0.8147 0.9806 0.3261 0.090 Uiso 1 1 calc R . .
H11C H 0.8649 0.8258 0.3771 0.090 Uiso 1 1 calc R . .
C12 C 0.4839(4) 1.2575(2) 0.6320(3) 0.0634(7) Uani 1 1 d . . .
H12A H 0.5421 1.2907 0.6741 0.095 Uiso 1 1 calc R . .
H12B H 0.3566 1.2653 0.6717 0.095 Uiso 1 1 calc R . .
H12C H 0.4925 1.3097 0.5547 0.095 Uiso 1 1 calc R . .
C20 C 1.1929(5) 0.7651(4) 1.1224(3) 0.0762(8) Uani 1 1 d . . .
H20A H 1.2918 0.7500 1.0547 0.114 Uiso 1 1 calc R . .
H20B H 1.2421 0.7425 1.1900 0.114 Uiso 1 1 calc R . .
H20C H 1.1266 0.8585 1.1130 0.114 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 C2 1.966(2) . ?
C2 C1 1.544(3) . ?
C2 C3 1.549(3) . ?
C2 H2 0.9800 . ?
F3 C10 1.330(3) . ?
F1 C10 1.330(3) . ?
C9 C4 1.391(3) . ?
C9 C8 1.395(3) . ?
C9 C1 1.518(3) . ?
C6 C7 1.387(4) . ?
C6 C5 1.403(3) . ?
C6 C12 1.508(3) . ?
C3 C4 1.511(3) . ?
C3 C14 1.526(3) . ?
C3 H3 0.9800 . ?
C14 C19 1.385(3) . ?
C14 C15 1.391(3) . ?
C8 C7 1.392(3) . ?
C8 C11 1.508(3) . ?
F2 C10 1.343(3) . ?
O1 C17 1.368(3) . ?
O1 C20 1.420(4) . ?
C4 C5 1.394(3) . ?
C7 H7 0.9300 . ?
C1 C10 1.514(3) . ?
C1 H1 0.9800 . ?
C15 C16 1.379(3) . ?
C15 H15 0.9300 . ?
C5 C13 1.507(3) . ?
C19 C18 1.393(3) . ?
C19 H19 0.9300 . ?
C17 C18 1.382(3) . ?
C17 C16 1.384(4) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C16 H16 0.9300 . ?
C18 H18 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 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
C1 C2 C3 107.31(16) . . ?
C1 C2 Br1 108.59(14) . . ?
C3 C2 Br1 109.23(14) . . ?
C1 C2 H2 110.5 . . ?
C3 C2 H2 110.5 . . ?
Br1 C2 H2 110.5 . . ?
C4 C9 C8 120.61(19) . . ?
C4 C9 C1 110.47(17) . . ?
C8 C9 C1 128.74(19) . . ?
C7 C6 C5 119.3(2) . . ?
C7 C6 C12 119.8(2) . . ?
C5 C6 C12 120.9(2) . . ?
C4 C3 C14 115.17(18) . . ?
C4 C3 C2 102.52(16) . . ?
C14 C3 C2 112.61(16) . . ?
C4 C3 H3 108.8 . . ?
C14 C3 H3 108.8 . . ?
C2 C3 H3 108.8 . . ?
C19 C14 C15 117.8(2) . . ?
C19 C14 C3 122.66(18) . . ?
C15 C14 C3 119.5(2) . . ?
C7 C8 C9 116.7(2) . . ?
C7 C8 C11 119.4(2) . . ?
C9 C8 C11 123.8(2) . . ?
C17 O1 C20 118.0(2) . . ?
C9 C4 C5 122.14(19) . . ?
C9 C4 C3 112.06(17) . . ?
C5 C4 C3 125.78(19) . . ?
C6 C7 C8 123.6(2) . . ?
C6 C7 H7 118.2 . . ?
C8 C7 H7 118.2 . . ?
C10 C1 C9 115.69(18) . . ?
C10 C1 C2 109.99(18) . . ?
C9 C1 C2 103.64(16) . . ?
C10 C1 H1 109.1 . . ?
C9 C1 H1 109.1 . . ?
C2 C1 H1 109.1 . . ?
C16 C15 C14 121.3(2) . . ?
C16 C15 H15 119.3 . . ?
C14 C15 H15 119.3 . . ?
C4 C5 C6 117.7(2) . . ?
C4 C5 C13 120.4(2) . . ?
C6 C5 C13 121.8(2) . . ?
C14 C19 C18 121.4(2) . . ?
C14 C19 H19 119.3 . . ?
C18 C19 H19 119.3 . . ?
O1 C17 C18 124.9(2) . . ?
O1 C17 C16 115.4(2) . . ?
C18 C17 C16 119.7(2) . . ?
F3 C10 F1 107.0(2) . . ?
F3 C10 F2 106.2(2) . . ?
F1 C10 F2 106.0(2) . . ?
F3 C10 C1 113.53(19) . . ?
F1 C10 C1 112.6(2) . . ?
F2 C10 C1 111.1(2) . . ?
C5 C13 H13A 109.5 . . ?
C5 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C5 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C16 C17 120.2(2) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C17 C18 C19 119.6(2) . . ?
C17 C18 H18 120.2 . . ?
C19 C18 H18 120.2 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C6 C12 H12A 109.5 . . ?
C6 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C6 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O1 C20 H20A 109.5 . . ?
O1 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O1 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
C1 C2 C3 C4 19.8(2) . . . . ?
Br1 C2 C3 C4 -97.69(16) . . . . ?
C1 C2 C3 C14 -104.52(19) . . . . ?
Br1 C2 C3 C14 137.94(15) . . . . ?
C4 C3 C14 C19 -11.0(3) . . . . ?
C2 C3 C14 C19 106.1(2) . . . . ?
C4 C3 C14 C15 168.51(19) . . . . ?
C2 C3 C14 C15 -74.4(2) . . . . ?
C4 C9 C8 C7 -0.5(3) . . . . ?
C1 C9 C8 C7 174.2(2) . . . . ?
C4 C9 C8 C11 -179.2(2) . . . . ?
C1 C9 C8 C11 -4.6(4) . . . . ?
C8 C9 C4 C5 0.4(3) . . . . ?
C1 C9 C4 C5 -175.14(19) . . . . ?
C8 C9 C4 C3 179.00(18) . . . . ?
C1 C9 C4 C3 3.5(2) . . . . ?
C14 C3 C4 C9 108.0(2) . . . . ?
C2 C3 C4 C9 -14.6(2) . . . . ?
C14 C3 C4 C5 -73.4(3) . . . . ?
C2 C3 C4 C5 163.9(2) . . . . ?
C5 C6 C7 C8 0.0(4) . . . . ?
C12 C6 C7 C8 -178.9(2) . . . . ?
C9 C8 C7 C6 0.3(3) . . . . ?
C11 C8 C7 C6 179.1(2) . . . . ?
C4 C9 C1 C10 -111.1(2) . . . . ?
C8 C9 C1 C10 73.8(3) . . . . ?
C4 C9 C1 C2 9.4(2) . . . . ?
C8 C9 C1 C2 -165.7(2) . . . . ?
C3 C2 C1 C10 106.1(2) . . . . ?
Br1 C2 C1 C10 -135.96(16) . . . . ?
C3 C2 C1 C9 -18.2(2) . . . . ?
Br1 C2 C1 C9 99.78(15) . . . . ?
C19 C14 C15 C16 -0.2(3) . . . . ?
C3 C14 C15 C16 -179.7(2) . . . . ?
C9 C4 C5 C6 -0.1(3) . . . . ?
C3 C4 C5 C6 -178.5(2) . . . . ?
C9 C4 C5 C13 178.2(2) . . . . ?
C3 C4 C5 C13 -0.2(4) . . . . ?
C7 C6 C5 C4 -0.1(3) . . . . ?
C12 C6 C5 C4 178.8(2) . . . . ?
C7 C6 C5 C13 -178.4(2) . . . . ?
C12 C6 C5 C13 0.5(3) . . . . ?
C15 C14 C19 C18 0.2(3) . . . . ?
C3 C14 C19 C18 179.7(2) . . . . ?
C20 O1 C17 C18 2.5(4) . . . . ?
C20 O1 C17 C16 -176.7(3) . . . . ?
C9 C1 C10 F3 56.8(3) . . . . ?
C2 C1 C10 F3 -60.1(3) . . . . ?
C9 C1 C10 F1 -65.0(3) . . . . ?
C2 C1 C10 F1 178.09(19) . . . . ?
C9 C1 C10 F2 176.39(19) . . . . ?
C2 C1 C10 F2 59.4(3) . . . . ?
C14 C15 C16 C17 0.3(3) . . . . ?
O1 C17 C16 C15 178.9(2) . . . . ?
C18 C17 C16 C15 -0.3(4) . . . . ?
O1 C17 C18 C19 -178.9(2) . . . . ?
C16 C17 C18 C19 0.3(4) . . . . ?
C14 C19 C18 C17 -0.3(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        72.49
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.690
_refine_diff_density_min         -0.491
_refine_diff_density_rms         0.060
####################################################################### 
# 
# 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_a283
_database_code_depnum_ccdc_archive 'CCDC 1413020'
_audit_update_record             
;
2015-07-15 deposited with the CCDC.
2016-11-24 downloaded from the CCDC.
;
_audit_creation_date             2014-11-21
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C20 H20 Br F3 O2'
_chemical_formula_sum            'C20 H20 Br F3 O2'
_chemical_formula_weight         429.27
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H20 F3 Br1 O2'
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'
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           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                   8.3533(5)
_cell_length_b                   9.4941(4)
_cell_length_c                   12.1934(7)
_cell_angle_alpha                100.216(4)
_cell_angle_beta                 97.306(5)
_cell_angle_gamma                100.289(4)
_cell_volume                     923.70(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4567
_cell_measurement_temperature    105(8)
_cell_measurement_theta_max      28.9480
_cell_measurement_theta_min      3.0580
_exptl_absorpt_coefficient_mu    2.265
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82160
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_unetI/netI     0.0378
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10460
_diffrn_reflns_theta_full        28.94
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.99
_diffrn_ambient_temperature      105(8)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.9984
_diffrn_measured_fraction_theta_max 0.9984
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -62.00  -36.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777 -178.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega  -90.00  -46.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777  -38.0000 -120.0000 44

#__ type_ start__ end____ width___ exp.time_
  3 omega   -5.00   24.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777  -99.0000   60.0000 29

#__ type_ start__ end____ width___ exp.time_
  4 omega  -16.00   17.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777  -99.0000    0.0000 33

#__ type_ start__ end____ width___ exp.time_
  5 omega  -20.00   18.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777  -99.0000 -180.0000 38

#__ type_ start__ end____ width___ exp.time_
  6 omega  -94.00  -42.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777 -178.0000  -60.0000 52

#__ type_ start__ end____ width___ exp.time_
  7 omega   -2.00   86.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8152   57.0000  -30.0000 88

#__ type_ start__ end____ width___ exp.time_
  8 omega   55.00   95.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8152  178.0000 -150.0000 40

#__ type_ start__ end____ width___ exp.time_
  9 omega  -15.00   79.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8152   19.0000  -90.0000 94

#__ type_ start__ end____ width___ exp.time_
 10 omega  -25.00   60.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8152  -99.0000  -30.0000 85

#__ type_ start__ end____ width___ exp.time_
 11 omega   34.00   61.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8152  -99.0000  120.0000 27
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0638978000
_diffrn_orient_matrix_UB_12      -0.0177861000
_diffrn_orient_matrix_UB_13      -0.0295853000
_diffrn_orient_matrix_UB_21      0.0557133000
_diffrn_orient_matrix_UB_22      0.0169671000
_diffrn_orient_matrix_UB_23      0.0517441000
_diffrn_orient_matrix_UB_31      -0.0216076000
_diffrn_orient_matrix_UB_32      -0.0735808000
_diffrn_orient_matrix_UB_33      0.0061321000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3711
_reflns_number_total             4114
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_refine_diff_density_max         0.413
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         4114
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0286
_refine_ls_restrained_S_all      1.048
_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)+(0.0268P)²+0.3223P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0627
_refine_ls_wR_factor_ref         0.0651
_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. 
;
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.45555(2) 0.14790(2) 0.770594(17) 0.02045(7) Uani 1 1 d . . .
F3 F 0.44588(14) 0.13301(12) 0.49433(10) 0.0225(3) Uani 1 1 d . . .
F2 F 0.19747(15) 0.10042(12) 0.40826(9) 0.0226(3) Uani 1 1 d . . .
F1 F 0.25419(15) -0.02672(11) 0.53162(10) 0.0229(3) Uani 1 1 d . . .
O2 O 0.46117(15) 0.60720(13) 0.77690(12) 0.0171(3) Uani 1 1 d . . .
O1 O -0.19217(16) 0.56029(14) 0.59874(12) 0.0185(3) Uani 1 1 d . . .
C12 C 0.2455(2) 0.48080(19) 1.03281(16) 0.0177(4) Uani 1 1 d . . .
H12A H 0.3538 0.4603 1.0470 0.027 Uiso 1 1 calc R . .
H12B H 0.2117 0.5157 1.1033 0.027 Uiso 1 1 calc R . .
H12C H 0.2471 0.5541 0.9877 0.027 Uiso 1 1 calc R . .
C2 C 0.2500(2) 0.22254(18) 0.59654(16) 0.0125(4) Uani 1 1 d . . .
H2 H 0.1809 0.2808 0.5710 0.015 Uiso 1 1 calc R . .
C3 C 0.3038(2) 0.25004(18) 0.70617(16) 0.0125(4) Uani 1 1 d . . .
C8 C -0.1068(2) 0.1460(2) 0.97239(16) 0.0156(4) Uani 1 1 d . . .
C20 C 0.5771(2) 0.7375(2) 0.77740(19) 0.0218(4) Uani 1 1 d . . .
H20A H 0.5827 0.7483 0.7011 0.033 Uiso 1 1 calc R . .
H20B H 0.6839 0.7315 0.8137 0.033 Uiso 1 1 calc R . .
H20C H 0.5428 0.8203 0.8177 0.033 Uiso 1 1 calc R . .
C18 C 0.3002(2) 0.60074(18) 0.73288(15) 0.0121(4) Uani 1 1 d . . .
C7 C -0.1012(2) 0.0888(2) 0.86058(16) 0.0170(4) Uani 1 1 d . . .
H7 H -0.1766 0.0045 0.8229 0.020 Uiso 1 1 calc R . .
C10 C 0.1254(2) 0.34263(19) 0.97053(15) 0.0136(4) Uani 1 1 d . . .
C16 C 0.0813(2) 0.69096(19) 0.63946(16) 0.0160(4) Uani 1 1 d . . .
H16 H 0.0456 0.7632 0.6062 0.019 Uiso 1 1 calc R . .
C11 C -0.2337(3) 0.0749(2) 1.03382(18) 0.0227(4) Uani 1 1 d . . .
H11A H -0.3387 0.0970 1.0096 0.034 Uiso 1 1 calc R . .
H11B H -0.2013 0.1115 1.1137 0.034 Uiso 1 1 calc R . .
H11C H -0.2421 -0.0291 1.0173 0.034 Uiso 1 1 calc R . .
C1 C 0.2883(2) 0.10824(19) 0.50965(17) 0.0160(4) Uani 1 1 d . . .
C17 C 0.2456(2) 0.70810(19) 0.68232(16) 0.0147(4) Uani 1 1 d . . .
H17 H 0.3203 0.7912 0.6776 0.018 Uiso 1 1 calc R . .
C14 C 0.0221(2) 0.46080(18) 0.69689(15) 0.0124(4) Uani 1 1 d . . .
H14 H -0.0533 0.3783 0.7021 0.015 Uiso 1 1 calc R . .
C5 C 0.1285(2) 0.28239(18) 0.85758(15) 0.0118(4) Uani 1 1 d . . .
C9 C 0.0080(2) 0.27297(19) 1.02546(16) 0.0150(4) Uani 1 1 d . . .
H9 H 0.0061 0.3127 1.1006 0.018 Uiso 1 1 calc R . .
C13 C 0.1872(2) 0.47650(18) 0.74068(15) 0.0112(4) Uani 1 1 d . . .
C19 C -0.3098(2) 0.4320(2) 0.60139(18) 0.0206(4) Uani 1 1 d . . .
H19A H -0.4156 0.4367 0.5626 0.031 Uiso 1 1 calc R . .
H19B H -0.3176 0.4263 0.6784 0.031 Uiso 1 1 calc R . .
H19C H -0.2752 0.3470 0.5649 0.031 Uiso 1 1 calc R . .
C6 C 0.0146(2) 0.15495(19) 0.80420(16) 0.0152(4) Uani 1 1 d . . .
H6 H 0.0166 0.1138 0.7294 0.018 Uiso 1 1 calc R . .
C15 C -0.0323(2) 0.56719(19) 0.64514(15) 0.0136(4) Uani 1 1 d . . .
C4 C 0.2515(2) 0.35885(18) 0.79375(15) 0.0114(4) Uani 1 1 d . . .
H4 H 0.3502 0.4080 0.8489 0.014 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 C3 1.9024(17) . ?
F3 C1 1.338(2) . ?
F2 C1 1.348(2) . ?
F1 C1 1.344(2) . ?
O2 C20 1.427(2) . ?
O2 C18 1.369(2) . ?
O1 C19 1.430(2) . ?
O1 C15 1.368(2) . ?
C12 C10 1.512(2) . ?
C2 C3 1.319(3) . ?
C2 C1 1.485(2) . ?
C3 C4 1.513(2) . ?
C8 C7 1.385(3) . ?
C8 C11 1.505(3) . ?
C8 C9 1.394(3) . ?
C18 C17 1.394(2) . ?
C18 C13 1.399(2) . ?
C7 C6 1.381(3) . ?
C10 C5 1.400(3) . ?
C10 C9 1.393(3) . ?
C16 C17 1.376(3) . ?
C16 C15 1.390(3) . ?
C14 C13 1.385(3) . ?
C14 C15 1.393(2) . ?
C5 C6 1.395(2) . ?
C5 C4 1.525(2) . ?
C13 C4 1.529(2) . ?

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
C18 O2 C20 117.06(14) . . ?
C15 O1 C19 116.90(14) . . ?
C3 C2 C1 126.74(16) . . ?
C2 C3 Br1 121.71(14) . . ?
C2 C3 C4 125.45(16) . . ?
C4 C3 Br1 112.81(12) . . ?
C7 C8 C11 121.23(17) . . ?
C7 C8 C9 117.53(17) . . ?
C9 C8 C11 121.24(17) . . ?
O2 C18 C17 124.25(16) . . ?
O2 C18 C13 115.94(15) . . ?
C17 C18 C13 119.81(17) . . ?
C6 C7 C8 121.08(17) . . ?
C5 C10 C12 121.40(17) . . ?
C9 C10 C12 119.96(17) . . ?
C9 C10 C5 118.64(17) . . ?
C17 C16 C15 120.95(16) . . ?
F3 C1 F2 106.02(15) . . ?
F3 C1 F1 106.77(14) . . ?
F3 C1 C2 113.70(16) . . ?
F2 C1 C2 110.50(15) . . ?
F1 C1 F2 105.81(15) . . ?
F1 C1 C2 113.48(15) . . ?
C16 C17 C18 119.94(17) . . ?
C13 C14 C15 120.73(16) . . ?
C10 C5 C4 119.96(16) . . ?
C6 C5 C10 118.98(17) . . ?
C6 C5 C4 121.02(16) . . ?
C10 C9 C8 122.66(17) . . ?
C18 C13 C4 118.55(16) . . ?
C14 C13 C18 119.51(16) . . ?
C14 C13 C4 121.89(15) . . ?
C7 C6 C5 121.10(17) . . ?
O1 C15 C16 116.19(15) . . ?
O1 C15 C14 124.76(16) . . ?
C16 C15 C14 119.05(17) . . ?
C3 C4 C5 111.39(14) . . ?
C3 C4 C13 110.99(14) . . ?
C5 C4 C13 112.62(14) . . ?

####################################################################### 
# 
# 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_a174
_database_code_depnum_ccdc_archive 'CCDC 1418365'
_audit_update_record             
;
2015-08-12 deposited with the CCDC.
2016-11-24 downloaded from the CCDC.
;
_audit_creation_date             2014-12-24
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C18 H15 Br2 F3'
_chemical_formula_sum            'C18 H15 Br2 F3'
_chemical_formula_weight         448.12
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C18 H15 f3 br2'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x-1/2, y, -z-1/2'
7 '-x-1/2, y-1/2, z'
8 'x, -y-1/2, z-1/2'

_cell_length_a                   16.4974(2)
_cell_length_b                   6.84171(10)
_cell_length_c                   28.6498(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3233.71(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    17306
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.1100
_cell_measurement_theta_min      4.0690
_exptl_absorpt_coefficient_mu    6.611
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60598
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.841
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tables
_exptl_crystal_F_000             1760
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0577
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            38981
_diffrn_reflns_theta_full        72.49
_diffrn_reflns_theta_max         72.49
_diffrn_reflns_theta_min         3.08
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3829
_diffrn_measured_fraction_theta_full 0.9964
_diffrn_measured_fraction_theta_max 0.9964
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -62.00   34.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   57.0000  150.0000 96

#__ type_ start__ end____ width___ exp.time_
  2 omega  -31.00   22.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000 -150.0000 53

#__ type_ start__ end____ width___ exp.time_
  3 omega   59.00  112.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787 -178.0000  -90.0000 53

#__ type_ start__ end____ width___ exp.time_
  4 omega   69.00   94.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000    0.0000 25

#__ type_ start__ end____ width___ exp.time_
  5 omega   36.00   89.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000 -120.0000 53

#__ type_ start__ end____ width___ exp.time_
  6 omega  106.00  132.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
  7 omega   53.00   87.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  150.0000 34

#__ type_ start__ end____ width___ exp.time_
  8 omega   58.00   85.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  -60.0000 27

#__ type_ start__ end____ width___ exp.time_
  9 omega  120.00  178.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000 -150.0000 58

#__ type_ start__ end____ width___ exp.time_
 10 omega   88.00  113.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000 -120.0000 25

#__ type_ start__ end____ width___ exp.time_
 11 omega   39.00   81.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  150.0000 42

#__ type_ start__ end____ width___ exp.time_
 12 omega   87.00  112.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  150.0000 25

#__ type_ start__ end____ width___ exp.time_
 13 omega   35.00   91.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   90.0000 56

#__ type_ start__ end____ width___ exp.time_
 14 omega   39.00   76.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000   30.0000 37

#__ type_ start__ end____ width___ exp.time_
 15 omega   46.00   72.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 16 omega   48.00   73.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   30.0000 25

#__ type_ start__ end____ width___ exp.time_
 17 omega   37.00   63.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 18 omega   29.00   63.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000    0.0000 34

#__ type_ start__ end____ width___ exp.time_
 19 omega   38.00   63.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787   73.0000  -44.0000 25

#__ type_ start__ end____ width___ exp.time_
 20 omega -116.00  -27.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -38.0000   30.0000 89

#__ type_ start__ end____ width___ exp.time_
 21 omega  -44.00   32.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000  -30.0000 76

#__ type_ start__ end____ width___ exp.time_
 22 omega   56.00  128.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787 -178.0000    0.0000 72

#__ type_ start__ end____ width___ exp.time_
 23 omega   62.00   89.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  178.0000  -90.0000 27

#__ type_ start__ end____ width___ exp.time_
 24 omega   85.00  119.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  178.0000  120.0000 34

#__ type_ start__ end____ width___ exp.time_
 25 omega   80.00  110.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000    0.0000 30

#__ type_ start__ end____ width___ exp.time_
 26 omega  134.00  176.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000  -90.0000 42

#__ type_ start__ end____ width___ exp.time_
 27 omega   83.00  158.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000  120.0000 75

#__ type_ start__ end____ width___ exp.time_
 28 omega  142.00  168.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
 29 omega   53.00   79.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
 30 omega   43.00   78.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000 -120.0000 35

#__ type_ start__ end____ width___ exp.time_
 31 omega   82.00  115.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000 -150.0000 33

#__ type_ start__ end____ width___ exp.time_
 32 omega  129.00  177.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  -30.0000 48

#__ type_ start__ end____ width___ exp.time_
 33 omega  102.00  136.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000 -150.0000 34

#__ type_ start__ end____ width___ exp.time_
 34 omega  114.00  154.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000  -30.0000 40

#__ type_ start__ end____ width___ exp.time_
 35 omega   89.00  115.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 36 omega  116.00  141.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000   90.0000 25

#__ type_ start__ end____ width___ exp.time_
 37 omega  119.00  145.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
 38 omega   60.00   86.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 39 omega   87.00  131.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000   90.0000 44

#__ type_ start__ end____ width___ exp.time_
 40 omega  107.00  149.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000  150.0000 42

#__ type_ start__ end____ width___ exp.time_
 41 omega   85.00  110.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000   30.0000 25

#__ type_ start__ end____ width___ exp.time_
 42 omega  121.00  155.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000   30.0000 34

#__ type_ start__ end____ width___ exp.time_
 43 omega  106.00  132.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 44 omega  153.00  178.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000 -120.0000 25

#__ type_ start__ end____ width___ exp.time_
 45 omega   86.00  111.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  -30.0000 25

#__ type_ start__ end____ width___ exp.time_
 46 omega  116.00  142.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 47 omega   80.00  105.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   30.0000 25

#__ type_ start__ end____ width___ exp.time_
 48 omega  153.00  178.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   30.0000 25

#__ type_ start__ end____ width___ exp.time_
 49 omega  100.00  126.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
 50 omega   90.00  170.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  150.0000 80

#__ type_ start__ end____ width___ exp.time_
 51 omega  110.00  136.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 52 omega   67.00   93.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 53 omega   73.00   99.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
 54 omega   59.00   97.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000 -120.0000 38

#__ type_ start__ end____ width___ exp.time_
 55 omega   33.00   65.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -15.0000  150.0000 32

#__ type_ start__ end____ width___ exp.time_
 56 omega  143.00  169.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -15.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
 57 omega   57.00   86.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -27.0000   -6.4743 29

#__ type_ start__ end____ width___ exp.time_
 58 omega   90.00  116.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
 59 omega   42.00   77.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  -60.0000 35

#__ type_ start__ end____ width___ exp.time_
 60 omega   81.00  108.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  -60.0000 27

#__ type_ start__ end____ width___ exp.time_
 61 omega   58.00   84.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
 62 omega   35.00  102.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  -90.0000 67
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0250997000
_diffrn_orient_matrix_UB_12      0.1035756000
_diffrn_orient_matrix_UB_13      0.0455123000
_diffrn_orient_matrix_UB_21      -0.0715044000
_diffrn_orient_matrix_UB_22      0.0971388000
_diffrn_orient_matrix_UB_23      -0.0256719000
_diffrn_orient_matrix_UB_31      -0.0545549000
_diffrn_orient_matrix_UB_32      -0.1747751000
_diffrn_orient_matrix_UB_33      0.0126868000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2961
_reflns_number_total             3212
_reflns_odcompleteness_completeness 95.10
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.95
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'J. Appl. Cryst. (2007) 40, 786-790'
_refine_diff_density_max         0.586
_refine_diff_density_min         -0.422
_refine_diff_density_rms         0.078
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3212
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0263
_refine_ls_R_factor_gt           0.0232
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0387P)²+0.9051P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0596
_refine_ls_wR_factor_ref         0.0612
_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. 
;
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br2 Br 0.570144(12) 0.58110(3) 0.665378(7) 0.01850(7) Uani 1 1 d . . .
Br1 Br 0.409918(12) 0.68184(3) 0.599587(7) 0.01908(7) Uani 1 1 d . . .
F1 F 0.40769(7) 1.10949(19) 0.70777(4) 0.0222(3) Uani 1 1 d . . .
F2 F 0.31124(7) 0.98620(19) 0.66704(4) 0.0215(2) Uani 1 1 d . . .
F3 F 0.33622(8) 1.29566(19) 0.66352(4) 0.0239(3) Uani 1 1 d . . .
C4 C 0.53300(11) 0.8422(3) 0.65641(6) 0.0161(4) Uani 1 1 d . . .
C3 C 0.46747(11) 0.8830(3) 0.63072(6) 0.0155(3) Uani 1 1 d . . .
C10 C 0.64581(12) 1.0869(3) 0.65766(7) 0.0191(4) Uani 1 1 d . . .
H10 H 0.6512 1.0719 0.6256 0.023 Uiso 1 1 calc R . .
C1 C 0.37096(12) 1.1194(3) 0.66594(6) 0.0174(4) Uani 1 1 d . . .
C6 C 0.57825(12) 1.0073(3) 0.72991(7) 0.0201(4) Uani 1 1 d . . .
H6 H 0.5385 0.9389 0.7462 0.024 Uiso 1 1 calc R . .
C2 C 0.43200(11) 1.0882(3) 0.62642(6) 0.0150(4) Uani 1 1 d . . .
H2 H 0.4768 1.1791 0.6322 0.018 Uiso 1 1 calc R . .
C5 C 0.58534(11) 0.9855(3) 0.68148(7) 0.0156(4) Uani 1 1 d . . .
C12 C 0.45069(12) 1.2075(3) 0.54332(7) 0.0171(4) Uani 1 1 d . . .
C8 C 0.69077(12) 1.2327(3) 0.72972(8) 0.0240(4) Uani 1 1 d . . .
H8 H 0.7259 1.3150 0.7458 0.029 Uiso 1 1 calc R . .
C9 C 0.69808(12) 1.2105(3) 0.68173(8) 0.0225(4) Uani 1 1 d . . .
H9 H 0.7381 1.2786 0.6656 0.027 Uiso 1 1 calc R . .
C15 C 0.28428(12) 1.1860(3) 0.52565(7) 0.0215(4) Uani 1 1 d . . .
H15 H 0.2289 1.1774 0.5201 0.026 Uiso 1 1 calc R . .
C11 C 0.39806(12) 1.1403(3) 0.57829(6) 0.0163(4) Uani 1 1 d . . .
C14 C 0.33553(12) 1.2559(3) 0.49095(7) 0.0207(4) Uani 1 1 d . . .
C16 C 0.31542(12) 1.1287(3) 0.56872(7) 0.0207(4) Uani 1 1 d . . .
H16 H 0.2803 1.0819 0.5915 0.025 Uiso 1 1 calc R . .
C17 C 0.54129(12) 1.2197(3) 0.55051(7) 0.0231(4) Uani 1 1 d . . .
H17A H 0.5528 1.3060 0.5761 0.035 Uiso 1 1 calc R . .
H17B H 0.5664 1.2691 0.5227 0.035 Uiso 1 1 calc R . .
H17C H 0.5622 1.0920 0.5573 0.035 Uiso 1 1 calc R . .
C7 C 0.63065(13) 1.1314(3) 0.75362(7) 0.0228(4) Uani 1 1 d . . .
H7 H 0.6255 1.1468 0.7857 0.027 Uiso 1 1 calc R . .
C18 C 0.30206(14) 1.3214(3) 0.44449(7) 0.0263(5) Uani 1 1 d . . .
H18A H 0.3128 1.2232 0.4214 0.039 Uiso 1 1 calc R . .
H18B H 0.3275 1.4418 0.4354 0.039 Uiso 1 1 calc R . .
H18C H 0.2446 1.3408 0.4471 0.039 Uiso 1 1 calc R . .
C13 C 0.41803(12) 1.2632(3) 0.50045(7) 0.0199(4) Uani 1 1 d . . .
H13 H 0.4530 1.3070 0.4772 0.024 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
Br2 C4 1.906(2) . ?
Br1 C3 1.8950(19) . ?
F1 C1 1.345(2) . ?
F2 C1 1.343(2) . ?
F3 C1 1.337(2) . ?
C4 C3 1.337(3) . ?
C4 C5 1.490(3) . ?
C3 C2 1.526(3) . ?
C10 H10 0.9300 . ?
C10 C5 1.394(3) . ?
C10 C9 1.391(3) . ?
C1 C2 1.530(2) . ?
C6 H6 0.9300 . ?
C6 C5 1.401(3) . ?
C6 C7 1.389(3) . ?
C2 H2 0.9800 . ?
C2 C11 1.531(2) . ?
C12 C11 1.403(3) . ?
C12 C17 1.511(3) . ?
C12 C13 1.394(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.388(3) . ?
C8 C7 1.391(3) . ?
C9 H9 0.9300 . ?
C15 H15 0.9300 . ?
C15 C14 1.390(3) . ?
C15 C16 1.393(3) . ?
C11 C16 1.393(3) . ?
C14 C18 1.509(3) . ?
C14 C13 1.389(3) . ?
C16 H16 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C7 H7 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C13 H13 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
C3 C4 Br2 121.96(15) . . ?
C3 C4 C5 126.62(18) . . ?
C5 C4 Br2 111.42(13) . . ?
C4 C3 Br1 120.85(15) . . ?
C4 C3 C2 123.10(17) . . ?
C2 C3 Br1 115.98(13) . . ?
C5 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C9 C10 C5 120.26(19) . . ?
F1 C1 C2 110.85(15) . . ?
F2 C1 F1 106.01(15) . . ?
F2 C1 C2 113.92(16) . . ?
F3 C1 F1 106.55(16) . . ?
F3 C1 F2 107.39(16) . . ?
F3 C1 C2 111.69(16) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C7 C6 C5 119.85(19) . . ?
C3 C2 C1 108.73(15) . . ?
C3 C2 H2 106.3 . . ?
C3 C2 C11 115.29(16) . . ?
C1 C2 H2 106.3 . . ?
C11 C2 C1 113.17(15) . . ?
C11 C2 H2 106.3 . . ?
C10 C5 C4 120.42(17) . . ?
C10 C5 C6 119.45(18) . . ?
C6 C5 C4 119.94(17) . . ?
C11 C12 C17 122.19(18) . . ?
C13 C12 C11 118.65(18) . . ?
C13 C12 C17 119.16(17) . . ?
C9 C8 H8 120.2 . . ?
C9 C8 C7 119.67(19) . . ?
C7 C8 H8 120.2 . . ?
C10 C9 H9 119.9 . . ?
C8 C9 C10 120.24(19) . . ?
C8 C9 H9 119.9 . . ?
C14 C15 H15 119.8 . . ?
C14 C15 C16 120.40(19) . . ?
C16 C15 H15 119.8 . . ?
C12 C11 C2 119.56(17) . . ?
C16 C11 C2 121.48(17) . . ?
C16 C11 C12 118.92(17) . . ?
C15 C14 C18 120.70(19) . . ?
C13 C14 C15 117.92(18) . . ?
C13 C14 C18 121.38(19) . . ?
C15 C16 C11 121.29(18) . . ?
C15 C16 H16 119.4 . . ?
C11 C16 H16 119.4 . . ?
C12 C17 H17A 109.5 . . ?
C12 C17 H17B 109.5 . . ?
C12 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C6 C7 C8 120.53(19) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C14 C18 H18A 109.5 . . ?
C14 C18 H18B 109.5 . . ?
C14 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C12 C13 H13 118.6 . . ?
C14 C13 C12 122.79(18) . . ?
C14 C13 H13 118.6 . . ?

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
Br2 C4 C3 Br1 -2.5(2) . . . . ?
Br2 C4 C3 C2 174.45(13) . . . . ?
Br2 C4 C5 C10 98.44(18) . . . . ?
Br2 C4 C5 C6 -76.5(2) . . . . ?
Br1 C3 C2 C1 88.61(16) . . . . ?
Br1 C3 C2 C11 -39.7(2) . . . . ?
F1 C1 C2 C3 62.7(2) . . . . ?
F1 C1 C2 C11 -167.79(16) . . . . ?
F2 C1 C2 C3 -56.7(2) . . . . ?
F2 C1 C2 C11 72.8(2) . . . . ?
F3 C1 C2 C3 -178.60(15) . . . . ?
F3 C1 C2 C11 -49.1(2) . . . . ?
C4 C3 C2 C1 -88.4(2) . . . . ?
C4 C3 C2 C11 143.26(18) . . . . ?
C3 C4 C5 C10 -82.0(3) . . . . ?
C3 C4 C5 C6 103.1(2) . . . . ?
C3 C2 C11 C12 -83.5(2) . . . . ?
C3 C2 C11 C16 98.7(2) . . . . ?
C1 C2 C11 C12 150.43(18) . . . . ?
C1 C2 C11 C16 -27.4(3) . . . . ?
C2 C11 C16 C15 176.59(19) . . . . ?
C5 C4 C3 Br1 178.00(14) . . . . ?
C5 C4 C3 C2 -5.1(3) . . . . ?
C5 C10 C9 C8 0.4(3) . . . . ?
C5 C6 C7 C8 -0.7(3) . . . . ?
C12 C11 C16 C15 -1.2(3) . . . . ?
C9 C10 C5 C4 -175.65(18) . . . . ?
C9 C10 C5 C6 -0.7(3) . . . . ?
C9 C8 C7 C6 0.4(3) . . . . ?
C15 C14 C13 C12 -1.4(3) . . . . ?
C11 C12 C13 C14 0.4(3) . . . . ?
C14 C15 C16 C11 0.2(3) . . . . ?
C16 C15 C14 C18 -179.0(2) . . . . ?
C16 C15 C14 C13 1.1(3) . . . . ?
C17 C12 C11 C2 3.6(3) . . . . ?
C17 C12 C11 C16 -178.5(2) . . . . ?
C17 C12 C13 C14 179.8(2) . . . . ?
C7 C6 C5 C4 175.79(19) . . . . ?
C7 C6 C5 C10 0.8(3) . . . . ?
C7 C8 C9 C10 -0.3(3) . . . . ?
C18 C14 C13 C12 178.7(2) . . . . ?
C13 C12 C11 C2 -176.91(18) . . . . ?
C13 C12 C11 C16 1.0(3) . . . . ?

####################################################################### 
# 
# 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_amp-1
_database_code_depnum_ccdc_archive 'CCDC 1498476'
_audit_update_record             
;
2016-08-09 deposited with the CCDC.
2016-11-24 downloaded from the CCDC.
;
_audit_creation_date             2016-08-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C16 H11 Br2 F3)'
_chemical_formula_sum            'C32 H22 Br4 F6'
_chemical_formula_weight         840.13
_chemical_melting_point          ?
_chemical_oxdiff_formula         'O3 N3 C10 H4 Br2'
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'
H H 0.0000 0.0000 '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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_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_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.1399(2)
_cell_length_b                   9.7404(3)
_cell_length_c                   22.8361(6)
_cell_angle_alpha                97.673(2)
_cell_angle_beta                 97.146(2)
_cell_angle_gamma                106.455(3)
_cell_volume                     1487.30(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    16076
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.9650
_cell_measurement_theta_min      3.9550
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    7.138
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.05657
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'translucent colorless'
_exptl_crystal_density_diffrn    1.876
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0832
_diffrn_reflns_av_unetI/netI     0.0397
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            33518
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.956
_diffrn_reflns_theta_min         3.965
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3829
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega    5.00   30.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   33.0000  118.0000 25

#__ type_ start__ end____ width___ exp.time_
  2 omega  -50.00   36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000  -30.0000 86

#__ type_ start__ end____ width___ exp.time_
  3 omega  -62.00   33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   57.0000   60.0000 95

#__ type_ start__ end____ width___ exp.time_
  4 omega -112.00  -15.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -57.0000 -180.0000 97

#__ type_ start__ end____ width___ exp.time_
  5 omega   14.00   78.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  -99.0000  120.0000 64

#__ type_ start__ end____ width___ exp.time_
  6 omega   88.00  122.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  178.0000   30.0000 34

#__ type_ start__ end____ width___ exp.time_
  7 omega   38.00   88.00   1.0000    1.4400
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  150.0000 50

#__ type_ start__ end____ width___ exp.time_
  8 omega   82.00  139.00   1.0000    1.4400
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000  150.0000 57

#__ type_ start__ end____ width___ exp.time_
  9 omega   74.00   99.00   1.0000    1.4400
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000   30.0000 25

#__ type_ start__ end____ width___ exp.time_
 10 omega   84.00  155.00   1.0000    1.4400
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000   60.0000 71

#__ type_ start__ end____ width___ exp.time_
 11 omega  127.00  167.00   1.0000    1.4400
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  -30.0000 40

#__ type_ start__ end____ width___ exp.time_
 12 omega   37.00   76.00   1.0000    1.4400
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  120.0000 39

#__ type_ start__ end____ width___ exp.time_
 13 omega   86.00  132.00   1.0000    1.4400
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000    0.0000 46

#__ type_ start__ end____ width___ exp.time_
 14 omega  125.00  177.00   1.0000    1.4400
omega____ theta____ kappa____ phi______ frames
    -      113.0000   15.0000  -60.0000 52

#__ type_ start__ end____ width___ exp.time_
 15 omega   85.00  113.00   1.0000    1.4400
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  -90.0000 28

#__ type_ start__ end____ width___ exp.time_
 16 omega  109.00  177.00   1.0000    1.4400
omega____ theta____ kappa____ phi______ frames
    -      113.0000   15.0000   30.0000 68

#__ type_ start__ end____ width___ exp.time_
 17 omega   89.00  115.00   1.0000    1.4400
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
 18 omega   36.00   61.00   1.0000    1.4400
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  120.0000 25

#__ type_ start__ end____ width___ exp.time_
 19 omega  112.00  138.00   1.0000    1.4400
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 20 omega   40.00   94.00   1.0000    1.4400
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000 -120.0000 54

#__ type_ start__ end____ width___ exp.time_
 21 omega   60.00   96.00   1.0000    1.4400
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000  150.0000 36

#__ type_ start__ end____ width___ exp.time_
 22 omega  115.00  145.00   1.0000    1.4400
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000  150.0000 30

#__ type_ start__ end____ width___ exp.time_
 23 omega   35.00   73.00   1.0000    1.4400
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  -90.0000 38

#__ type_ start__ end____ width___ exp.time_
 24 omega   38.00   65.00   1.0000    1.4400
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000   90.0000 27

#__ type_ start__ end____ width___ exp.time_
 25 omega   69.00  114.00   1.0000    1.4400
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  -30.0000 45

#__ type_ start__ end____ width___ exp.time_
 26 omega   67.00  106.00   1.0000    1.4400
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000 -180.0000 39

#__ type_ start__ end____ width___ exp.time_
 27 omega   36.00   90.00   1.0000    1.4400
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000 -180.0000 54

#__ type_ start__ end____ width___ exp.time_
 28 omega   54.00   79.00   1.0000    1.4400
omega____ theta____ kappa____ phi______ frames
    -      113.0000   15.0000  -60.0000 25

#__ type_ start__ end____ width___ exp.time_
 29 omega   55.00   94.00   1.0000    1.4400
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  120.0000 39

#__ type_ start__ end____ width___ exp.time_
 30 omega   99.00  142.00   1.0000    1.4400
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000 -120.0000 43

#__ type_ start__ end____ width___ exp.time_
 31 omega   58.00   84.00   1.0000    1.4400
omega____ theta____ kappa____ phi______ frames
    -      113.0000   15.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
 32 omega   29.00   71.00   1.0000    1.4400
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  150.0000 42

#__ type_ start__ end____ width___ exp.time_
 33 omega   70.00  110.00   1.0000    1.4400
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -90.0000   80.1221 40

#__ type_ start__ end____ width___ exp.time_
 34 omega   76.00  113.00   1.0000    1.4400
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000   90.0000 37

#__ type_ start__ end____ width___ exp.time_
 35 omega  120.00  154.00   1.0000    1.4400
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000 -120.0000 34

#__ type_ start__ end____ width___ exp.time_
 36 omega   35.00   66.00   1.0000    1.4400
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000 -120.0000 31

#__ type_ start__ end____ width___ exp.time_
 37 omega   55.00   80.00   1.0000    1.4400
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   30.0000 25

#__ type_ start__ end____ width___ exp.time_
 38 omega   45.00   73.00   1.0000    1.4400
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000 -180.0000 28

#__ type_ start__ end____ width___ exp.time_
 39 omega   95.00  122.00   1.0000    1.4400
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000 -180.0000 27

#__ type_ start__ end____ width___ exp.time_
 40 omega   71.00   98.00   1.0000    1.4400
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000    0.0000 27

#__ type_ start__ end____ width___ exp.time_
 41 omega   80.00  105.00   1.0000    1.4400
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  -30.0000 25

#__ type_ start__ end____ width___ exp.time_
 42 omega   54.00  115.00   1.0000    1.4400
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  150.0000 61

#__ type_ start__ end____ width___ exp.time_
 43 omega  125.00  150.00   1.0000    1.4400
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000 -150.0000 25

#__ type_ start__ end____ width___ exp.time_
 44 omega  145.00  172.00   1.0000    1.4400
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000 -120.0000 27

#__ type_ start__ end____ width___ exp.time_
 45 omega   87.00  117.00   1.0000    1.4400
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000  -60.0000 30

#__ type_ start__ end____ width___ exp.time_
 46 omega   32.00  107.00   1.0000    1.4400
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -83.0000  -91.6540 75

#__ type_ start__ end____ width___ exp.time_
 47 omega -121.00    3.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -19.0000  -30.0000 124

#__ type_ start__ end____ width___ exp.time_
 48 omega  -61.00  -15.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -38.0000 -120.0000 46

#__ type_ start__ end____ width___ exp.time_
 49 omega  -93.00  -68.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -38.0000 -120.0000 25

#__ type_ start__ end____ width___ exp.time_
 50 omega   57.00  116.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  178.0000  -90.0000 59

#__ type_ start__ end____ width___ exp.time_
 51 omega   10.00   35.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       44.0000   80.0000  -63.8689 25

#__ type_ start__ end____ width___ exp.time_
 52 omega    8.00   33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       44.0000   86.0000    5.8329 25

#__ type_ start__ end____ width___ exp.time_
 53 omega    7.00   32.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       44.0000   87.0000  134.4845 25

#__ type_ start__ end____ width___ exp.time_
 54 omega   12.00   37.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       48.0000   84.0000 -149.1265 25

#__ type_ start__ end____ width___ exp.time_
 55 omega   12.00   37.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       48.0000   84.0000  -14.4003 25

#__ type_ start__ end____ width___ exp.time_
 56 omega   17.00   42.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       52.0000   81.0000 -114.3568 25

#__ type_ start__ end____ width___ exp.time_
 57 omega   18.00   43.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       52.0000   80.0000  -52.9147 25

#__ type_ start__ end____ width___ exp.time_
 58 omega   22.00   47.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   78.0000  151.6868 25

#__ type_ start__ end____ width___ exp.time_
 59 omega   23.00   48.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   78.0000   43.0875 25

#__ type_ start__ end____ width___ exp.time_
 60 omega   31.00   64.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       64.0000   76.0000  -37.8219 33

#__ type_ start__ end____ width___ exp.time_
 61 omega   35.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   76.0000  -96.4991 28

#__ type_ start__ end____ width___ exp.time_
 62 omega   36.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   75.0000   98.6848 27

#__ type_ start__ end____ width___ exp.time_
 63 omega  106.00  133.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   76.0000  -96.4991 27

#__ type_ start__ end____ width___ exp.time_
 64 omega   35.00   62.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   76.0000  -68.6818 27

#__ type_ start__ end____ width___ exp.time_
 65 omega   35.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   75.0000   23.4880 28

#__ type_ start__ end____ width___ exp.time_
 66 omega  110.00  137.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   75.0000   23.4880 27

#__ type_ start__ end____ width___ exp.time_
 67 omega   35.00   61.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   76.0000  178.0113 26

#__ type_ start__ end____ width___ exp.time_
 68 omega   39.00   65.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       72.0000   75.0000 -155.9476 26

#__ type_ start__ end____ width___ exp.time_
 69 omega   38.00   70.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       72.0000   77.0000   60.7720 32

#__ type_ start__ end____ width___ exp.time_
 70 omega   40.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       72.0000   72.0000 -115.3198 35

#__ type_ start__ end____ width___ exp.time_
 71 omega   38.00   67.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       72.0000   77.0000  131.0625 29

#__ type_ start__ end____ width___ exp.time_
 72 omega   54.00   85.00   1.0000    1.4400
omega____ theta____ kappa____ phi______ frames
    -       84.0000   64.0000  -73.9210 31

#__ type_ start__ end____ width___ exp.time_
 73 omega   59.00   86.00   1.0000    1.4400
omega____ theta____ kappa____ phi______ frames
    -       88.0000   58.0000 -117.5758 27

#__ type_ start__ end____ width___ exp.time_
 74 omega   56.00   83.00   1.0000    1.4400
omega____ theta____ kappa____ phi______ frames
    -       88.0000   70.0000  -18.7294 27

#__ type_ start__ end____ width___ exp.time_
 75 omega   60.00   89.00   1.0000    1.4400
omega____ theta____ kappa____ phi______ frames
    -       88.0000   56.0000  108.5222 29

#__ type_ start__ end____ width___ exp.time_
 76 omega   61.00   89.00   1.0000    1.4400
omega____ theta____ kappa____ phi______ frames
    -       92.0000   66.0000   33.8229 28

#__ type_ start__ end____ width___ exp.time_
 77 omega   61.00   86.00   1.0000    1.4400
omega____ theta____ kappa____ phi______ frames
    -       92.0000   70.0000  156.7869 25

#__ type_ start__ end____ width___ exp.time_
 78 omega   80.00  111.00   1.0000    1.4400
omega____ theta____ kappa____ phi______ frames
    -      112.0000   69.0000 -119.9141 31

#__ type_ start__ end____ width___ exp.time_
 79 omega  134.00  167.00   1.0000    1.4400
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000 -150.0000 33

#__ type_ start__ end____ width___ exp.time_
 80 omega   84.00  121.00   1.0000    1.4400
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  -90.0000 37

#__ type_ start__ end____ width___ exp.time_
 81 omega   87.00  119.00   1.0000    1.4400
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000 -150.0000 32

#__ type_ start__ end____ width___ exp.time_
 82 omega   79.00  106.00   1.0000    1.4400
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000    0.0000 27

#__ type_ start__ end____ width___ exp.time_
 83 omega  140.00  168.00   1.0000    1.4400
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  120.0000 28

#__ type_ start__ end____ width___ exp.time_
 84 omega   80.00  105.00   1.0000    1.4400
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  120.0000 25

#__ type_ start__ end____ width___ exp.time_
 85 omega   83.00  157.00   1.0000    1.4400
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000   90.0000 74

#__ type_ start__ end____ width___ exp.time_
 86 omega   87.00  169.00   1.0000    1.4400
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  150.0000 82

#__ type_ start__ end____ width___ exp.time_
 87 omega   84.00  114.00   1.0000    1.4400
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  -60.0000 30

#__ type_ start__ end____ width___ exp.time_
 88 omega   81.00  121.00   1.0000    1.4400
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000 -120.0000 40

#__ type_ start__ end____ width___ exp.time_
 89 omega   86.00  126.00   1.0000    1.4400
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  120.0000 40

#__ type_ start__ end____ width___ exp.time_
 90 omega   80.00  105.00   1.0000    1.4400
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  150.0000 25

#__ type_ start__ end____ width___ exp.time_
 91 omega  142.00  178.00   1.0000    1.4400
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   90.0000 36

#__ type_ start__ end____ width___ exp.time_
 92 omega   85.00  163.00   1.0000    1.4400
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000 -180.0000 78

#__ type_ start__ end____ width___ exp.time_
 93 omega   80.00  121.00   1.0000    1.4400
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   90.0000 41

#__ type_ start__ end____ width___ exp.time_
 94 omega  119.00  144.00   1.0000    1.4400
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000 -180.0000 25

#__ type_ start__ end____ width___ exp.time_
 95 omega  125.00  154.00   1.0000    1.4400
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  150.0000 29

#__ type_ start__ end____ width___ exp.time_
 96 omega   80.00  109.00   1.0000    1.4400
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000 -150.0000 29

#__ type_ start__ end____ width___ exp.time_
 97 omega   79.00  108.00   1.0000    1.4400
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000 -180.0000 29

#__ type_ start__ end____ width___ exp.time_
 98 omega  141.00  167.00   1.0000    1.4400
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
 99 omega   80.00  124.00   1.0000    1.4400
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   60.0000 44

#__ type_ start__ end____ width___ exp.time_
100 omega   79.00  105.00   1.0000    1.4400
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
101 omega  115.00  155.00   1.0000    1.4400
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   30.0000 40

#__ type_ start__ end____ width___ exp.time_
102 omega   79.00  104.00   1.0000    1.4400
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   30.0000 25

#__ type_ start__ end____ width___ exp.time_
103 omega  139.00  165.00   1.0000    1.4400
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
104 omega   83.00  110.00   1.0000    1.4400
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000    0.0000 27

#__ type_ start__ end____ width___ exp.time_
105 omega   79.00  119.00   1.0000    1.4400
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  -90.0000 40

#__ type_ start__ end____ width___ exp.time_
106 omega  116.00  143.00   1.0000    1.4400
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  -60.0000 27

#__ type_ start__ end____ width___ exp.time_
107 omega   79.00  107.00   1.0000    1.4400
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  -60.0000 28
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1863982000
_diffrn_orient_matrix_UB_12      0.0828748000
_diffrn_orient_matrix_UB_13      -0.0228947000
_diffrn_orient_matrix_UB_21      -0.1042950000
_diffrn_orient_matrix_UB_22      0.1100598000
_diffrn_orient_matrix_UB_23      -0.0183225000
_diffrn_orient_matrix_UB_31      0.0807142000
_diffrn_orient_matrix_UB_32      0.0953914000
_diffrn_orient_matrix_UB_33      0.0625528000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5173
_reflns_number_total             5637
_reflns_odcompleteness_completeness 94.21
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.95
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         1.038
_refine_diff_density_min         -0.789
_refine_diff_density_rms         0.160
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         5637
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0469
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0955P)²+0.1069P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1234
_refine_ls_wR_factor_ref         0.1276
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C2A(H2A), C2(H2)
2.b Aromatic/amide H refined with riding coordinates:
 C12A(H12A), C14(H14), C7(H7), C7A(H7A), C8A(H8A), C8(H8), C12(H12), C13(H13),
 C6(H6), C16(H16), C9(H9), C6A(H6A), C15(H15), C10(H10), C14A(H14A), C16A(H16A),
  C13A(H13A), C10A(H10A), C15A(H15A), C9A(H9A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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
Br2A Br 0.25738(5) 0.35087(4) 0.65531(2) 0.03938(13) Uani 1 1 d . . . . .
Br1 Br 0.60143(5) 0.81799(4) 1.03044(2) 0.03988(13) Uani 1 1 d . . . . .
Br2 Br 0.81081(5) 0.99517(4) 0.93025(2) 0.03894(13) Uani 1 1 d . . . . .
Br1A Br 0.44697(5) 0.62157(4) 0.58438(2) 0.04423(14) Uani 1 1 d . . . . .
F1A F -0.2286(3) 0.4913(2) 0.74658(10) 0.0429(5) Uani 1 1 d . . . . .
F2 F 0.5541(4) 0.6221(3) 0.81429(12) 0.0559(6) Uani 1 1 d . . . . .
F3 F 0.7453(3) 0.8253(3) 0.80043(11) 0.0527(6) Uani 1 1 d . . . . .
F1 F 0.4621(3) 0.7293(3) 0.74430(10) 0.0490(5) Uani 1 1 d . . . . .
F3A F 0.0525(3) 0.6521(2) 0.75012(10) 0.0453(5) Uani 1 1 d . . . . .
F2A F 0.0413(3) 0.4352(3) 0.76275(10) 0.0463(5) Uani 1 1 d . . . . .
C4 C 0.4749(5) 0.7804(4) 0.94898(16) 0.0355(7) Uani 1 1 d . . . . .
C3A C 0.1290(5) 0.4921(3) 0.64224(15) 0.0328(6) Uani 1 1 d . . . . .
C3 C 0.5576(5) 0.8521(4) 0.90831(16) 0.0347(6) Uani 1 1 d . . . . .
C11A C -0.2179(5) 0.3208(3) 0.63699(15) 0.0343(7) Uani 1 1 d . . . . .
C4A C 0.2030(5) 0.6002(4) 0.61339(16) 0.0355(7) Uani 1 1 d . . . . .
C12A C -0.3205(5) 0.3027(4) 0.57949(17) 0.0390(7) Uani 1 1 d . . . . .
H12A H -0.2935 0.3790 0.5582 0.047 Uiso 1 1 calc R . . . .
C14 C 0.3236(6) 1.2133(4) 0.80194(19) 0.0466(8) Uani 1 1 d . . . . .
H14 H 0.2947 1.2974 0.7947 0.056 Uiso 1 1 calc R . . . .
C7 C -0.0790(6) 0.6053(5) 0.92569(19) 0.0457(8) Uani 1 1 d . . . . .
H7 H -0.1932 0.6336 0.9245 0.055 Uiso 1 1 calc R . . . .
C7A C -0.0680(6) 0.8145(4) 0.52872(18) 0.0436(8) Uani 1 1 d . . . . .
H7A H -0.1290 0.8103 0.4898 0.052 Uiso 1 1 calc R . . . .
C8A C -0.0633(6) 0.9264(4) 0.57451(19) 0.0445(8) Uani 1 1 d . . . . .
H8A H -0.1216 0.9972 0.5660 0.053 Uiso 1 1 calc R . . . .
C2A C -0.0699(5) 0.4700(4) 0.66327(16) 0.0356(7) Uani 1 1 d . . . . .
H2A H -0.1265 0.5399 0.6465 0.043 Uiso 1 1 calc R . . . .
C8 C -0.0935(6) 0.4593(4) 0.91748(18) 0.0458(8) Uani 1 1 d . . . . .
H8 H -0.2171 0.3895 0.9112 0.055 Uiso 1 1 calc R . . . .
C5A C 0.1102(5) 0.7136(4) 0.60021(17) 0.0369(7) Uani 1 1 d . . . . .
C12 C 0.2247(5) 0.9749(4) 0.82797(16) 0.0381(7) Uani 1 1 d . . . . .
H12 H 0.1279 0.8988 0.8375 0.046 Uiso 1 1 calc R . . . .
C13 C 0.1799(6) 1.0986(4) 0.81612(18) 0.0442(8) Uani 1 1 d . . . . .
H13 H 0.0530 1.1051 0.8176 0.053 Uiso 1 1 calc R . . . .
C1 C 0.5566(6) 0.7516(4) 0.80042(18) 0.0423(8) Uani 1 1 d . . . . .
C2 C 0.4555(5) 0.8277(4) 0.84389(16) 0.0368(7) Uani 1 1 d . . . . .
H2 H 0.3246 0.7579 0.8421 0.044 Uiso 1 1 calc R . . . .
C5 C 0.2773(5) 0.6680(4) 0.93732(16) 0.0362(7) Uani 1 1 d . . . . .
C6 C 0.1061(6) 0.7101(4) 0.93571(17) 0.0408(7) Uani 1 1 d . . . . .
H6 H 0.1154 0.8083 0.9413 0.049 Uiso 1 1 calc R . . . .
C16 C 0.5557(5) 1.0767(5) 0.81071(18) 0.0448(8) Uani 1 1 d . . . . .
H16 H 0.6822 1.0700 0.8086 0.054 Uiso 1 1 calc R . . . .
C9 C 0.0763(6) 0.4168(4) 0.91854(19) 0.0471(8) Uani 1 1 d . . . . .
H9 H 0.0660 0.3184 0.9126 0.057 Uiso 1 1 calc R . . . .
C6A C 0.0200(5) 0.7090(4) 0.54217(17) 0.0397(7) Uani 1 1 d . . . . .
H6A H 0.0182 0.6345 0.5118 0.048 Uiso 1 1 calc R . . . .
C1A C -0.0499(5) 0.5108(4) 0.73064(17) 0.0383(7) Uani 1 1 d . . . . .
C15 C 0.5095(6) 1.2004(5) 0.79879(19) 0.0486(9) Uani 1 1 d . . . . .
H15 H 0.6055 1.2758 0.7885 0.058 Uiso 1 1 calc R . . . .
C10 C 0.2615(6) 0.5202(4) 0.92837(18) 0.0438(8) Uani 1 1 d . . . . .
H10 H 0.3750 0.4911 0.9290 0.053 Uiso 1 1 calc R . . . .
C14A C -0.5059(6) 0.0574(4) 0.58407(19) 0.0446(8) Uani 1 1 d . . . . .
H14A H -0.6028 -0.0296 0.5666 0.054 Uiso 1 1 calc R . . . .
C16A C -0.2557(6) 0.2034(4) 0.66798(18) 0.0411(7) Uani 1 1 d . . . . .
H16A H -0.1834 0.2121 0.7058 0.049 Uiso 1 1 calc R . . . .
C11 C 0.4144(5) 0.9632(4) 0.82575(15) 0.0357(7) Uani 1 1 d . . . . .
C13A C -0.4632(5) 0.1720(4) 0.55324(18) 0.0422(8) Uani 1 1 d . . . . .
H13A H -0.5306 0.1615 0.5146 0.051 Uiso 1 1 calc R . . . .
C10A C 0.1149(5) 0.8271(4) 0.64547(18) 0.0401(7) Uani 1 1 d . . . . .
H10A H 0.1766 0.8320 0.6844 0.048 Uiso 1 1 calc R . . . .
C15A C -0.4023(6) 0.0736(4) 0.6416(2) 0.0466(8) Uani 1 1 d . . . . .
H15A H -0.4311 -0.0029 0.6628 0.056 Uiso 1 1 calc R . . . .
C9A C 0.0270(6) 0.9331(4) 0.63225(19) 0.0445(8) Uani 1 1 d . . . . .
H9A H 0.0293 1.0081 0.6624 0.053 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
Br2A C3A 1.891(3) . ?
Br1 C4 1.903(4) . ?
Br2 C3 1.904(3) . ?
Br1A C4A 1.907(3) . ?
F1A C1A 1.339(4) . ?
F2 C1 1.337(5) . ?
F3 C1 1.335(5) . ?
F1 C1 1.331(5) . ?
F3A C1A 1.347(4) . ?
F2A C1A 1.342(4) . ?
C4 C3 1.332(5) . ?
C4 C5 1.488(5) . ?
C3A C4A 1.334(5) . ?
C3A C2A 1.522(4) . ?
C3 C2 1.515(5) . ?
C11A C12A 1.385(5) . ?
C11A C2A 1.526(4) . ?
C11A C16A 1.403(5) . ?
C4A C5A 1.484(5) . ?
C12A H12A 0.9300 . ?
C12A C13A 1.389(5) . ?
C14 H14 0.9300 . ?
C14 C13 1.392(6) . ?
C14 C15 1.378(6) . ?
C7 H7 0.9300 . ?
C7 C8 1.382(6) . ?
C7 C6 1.393(6) . ?
C7A H7A 0.9300 . ?
C7A C8A 1.396(6) . ?
C7A C6A 1.395(5) . ?
C8A H8A 0.9300 . ?
C8A C9A 1.378(6) . ?
C2A H2A 0.9800 . ?
C2A C1A 1.515(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.386(6) . ?
C5A C6A 1.389(5) . ?
C5A C10A 1.399(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.383(5) . ?
C12 C11 1.397(5) . ?
C13 H13 0.9300 . ?
C1 C2 1.530(5) . ?
C2 H2 0.9800 . ?
C2 C11 1.527(5) . ?
C5 C6 1.393(5) . ?
C5 C10 1.397(5) . ?
C6 H6 0.9300 . ?
C16 H16 0.9300 . ?
C16 C15 1.388(6) . ?
C16 C11 1.383(5) . ?
C9 H9 0.9300 . ?
C9 C10 1.387(6) . ?
C6A H6A 0.9300 . ?
C15 H15 0.9300 . ?
C10 H10 0.9300 . ?
C14A H14A 0.9300 . ?
C14A C13A 1.380(6) . ?
C14A C15A 1.392(6) . ?
C16A H16A 0.9300 . ?
C16A C15A 1.395(6) . ?
C13A H13A 0.9300 . ?
C10A H10A 0.9300 . ?
C10A C9A 1.398(5) . ?
C15A H15A 0.9300 . ?
C9A H9A 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
C3 C4 Br1 121.9(3) . . ?
C3 C4 C5 125.2(3) . . ?
C5 C4 Br1 112.9(2) . . ?
C4A C3A Br2A 122.0(3) . . ?
C4A C3A C2A 121.9(3) . . ?
C2A C3A Br2A 116.1(2) . . ?
C4 C3 Br2 120.4(3) . . ?
C4 C3 C2 122.6(3) . . ?
C2 C3 Br2 117.0(2) . . ?
C12A C11A C2A 117.3(3) . . ?
C12A C11A C16A 119.1(3) . . ?
C16A C11A C2A 123.7(3) . . ?
C3A C4A Br1A 121.3(3) . . ?
C3A C4A C5A 125.5(3) . . ?
C5A C4A Br1A 113.2(2) . . ?
C11A C12A H12A 119.6 . . ?
C11A C12A C13A 120.8(3) . . ?
C13A C12A H12A 119.6 . . ?
C13 C14 H14 120.5 . . ?
C15 C14 H14 120.5 . . ?
C15 C14 C13 119.0(4) . . ?
C8 C7 H7 119.9 . . ?
C8 C7 C6 120.1(4) . . ?
C6 C7 H7 119.9 . . ?
C8A C7A H7A 120.5 . . ?
C6A C7A H7A 120.5 . . ?
C6A C7A C8A 119.1(4) . . ?
C7A C8A H8A 119.7 . . ?
C9A C8A C7A 120.7(4) . . ?
C9A C8A H8A 119.7 . . ?
C3A C2A C11A 113.0(3) . . ?
C3A C2A H2A 105.3 . . ?
C11A C2A H2A 105.3 . . ?
C1A C2A C3A 113.0(3) . . ?
C1A C2A C11A 113.7(3) . . ?
C1A C2A H2A 105.3 . . ?
C7 C8 H8 120.0 . . ?
C7 C8 C9 120.0(4) . . ?
C9 C8 H8 120.0 . . ?
C6A C5A C4A 120.0(3) . . ?
C6A C5A C10A 119.2(3) . . ?
C10A C5A C4A 120.8(3) . . ?
C13 C12 H12 119.7 . . ?
C13 C12 C11 120.6(3) . . ?
C11 C12 H12 119.7 . . ?
C14 C13 H13 119.9 . . ?
C12 C13 C14 120.3(4) . . ?
C12 C13 H13 119.9 . . ?
F2 C1 C2 109.9(3) . . ?
F3 C1 F2 107.2(3) . . ?
F3 C1 C2 114.2(3) . . ?
F1 C1 F2 107.8(3) . . ?
F1 C1 F3 106.6(3) . . ?
F1 C1 C2 110.8(3) . . ?
C3 C2 C1 112.1(3) . . ?
C3 C2 H2 105.2 . . ?
C3 C2 C11 113.4(3) . . ?
C1 C2 H2 105.2 . . ?
C11 C2 C1 114.7(3) . . ?
C11 C2 H2 105.2 . . ?
C6 C5 C4 119.9(3) . . ?
C6 C5 C10 119.5(3) . . ?
C10 C5 C4 120.6(3) . . ?
C7 C6 C5 120.1(4) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C15 C16 H16 119.9 . . ?
C11 C16 H16 119.9 . . ?
C11 C16 C15 120.3(3) . . ?
C8 C9 H9 119.8 . . ?
C8 C9 C10 120.4(4) . . ?
C10 C9 H9 119.8 . . ?
C7A C6A H6A 119.5 . . ?
C5A C6A C7A 121.0(4) . . ?
C5A C6A H6A 119.5 . . ?
F1A C1A F3A 106.6(3) . . ?
F1A C1A F2A 106.6(3) . . ?
F1A C1A C2A 110.5(3) . . ?
F3A C1A C2A 111.4(3) . . ?
F2A C1A F3A 106.3(3) . . ?
F2A C1A C2A 115.0(3) . . ?
C14 C15 C16 121.0(4) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C5 C10 H10 120.1 . . ?
C9 C10 C5 119.9(4) . . ?
C9 C10 H10 120.1 . . ?
C13A C14A H14A 120.4 . . ?
C13A C14A C15A 119.2(3) . . ?
C15A C14A H14A 120.4 . . ?
C11A C16A H16A 120.2 . . ?
C15A C16A C11A 119.6(4) . . ?
C15A C16A H16A 120.2 . . ?
C12 C11 C2 117.1(3) . . ?
C16 C11 C12 118.8(3) . . ?
C16 C11 C2 124.0(3) . . ?
C12A C13A H13A 119.7 . . ?
C14A C13A C12A 120.6(4) . . ?
C14A C13A H13A 119.7 . . ?
C5A C10A H10A 120.0 . . ?
C9A C10A C5A 120.0(4) . . ?
C9A C10A H10A 120.0 . . ?
C14A C15A C16A 120.7(4) . . ?
C14A C15A H15A 119.7 . . ?
C16A C15A H15A 119.7 . . ?
C8A C9A C10A 120.0(4) . . ?
C8A C9A H9A 120.0 . . ?
C10A C9A H9A 120.0 . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_avv_21
_database_code_depnum_ccdc_archive 'CCDC 1498617'
_audit_update_record             
;
2016-08-10 deposited with the CCDC.
2016-11-24 downloaded from the CCDC.
;
_audit_creation_date             2014-10-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C17 H12 Br F3'
_chemical_formula_sum            'C17 H12 Br F3'
_chemical_formula_weight         353.18
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 h7 f3 Br2'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y, -z+1/2'
3 'x+1/2, y+1/2, z'
4 '-x+1/2, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x, -y, z-1/2'
7 '-x+1/2, -y+1/2, -z'
8 'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   22.8229(15)
_cell_length_b                   7.4881(4)
_cell_length_c                   16.5828(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.102(7)
_cell_angle_gamma                90.00
_cell_volume                     2771.0(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2440
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.6500
_cell_measurement_theta_min      3.9610
_exptl_absorpt_coefficient_mu    4.282
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76650
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.693
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.09
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_av_unetI/netI     0.0461
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7552
_diffrn_reflns_theta_full        72.46
_diffrn_reflns_theta_max         72.46
_diffrn_reflns_theta_min         3.96
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3829
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -113.00  -83.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -57.0000  -30.0000 30

#__ type_ start__ end____ width___ exp.time_
  2 omega  -74.00  -15.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -57.0000  -30.0000 59

#__ type_ start__ end____ width___ exp.time_
  3 omega -128.00  -38.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  178.0000 -150.0000 90

#__ type_ start__ end____ width___ exp.time_
  4 omega  -29.00   36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000 -150.0000 65

#__ type_ start__ end____ width___ exp.time_
  5 omega   59.00   97.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  178.0000  -30.0000 38

#__ type_ start__ end____ width___ exp.time_
  6 omega   72.00   97.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  -30.0000 25

#__ type_ start__ end____ width___ exp.time_
  7 omega   58.00  147.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000   30.0000 89

#__ type_ start__ end____ width___ exp.time_
  8 omega   82.00  108.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
  9 omega  123.00  149.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
 10 omega   58.00   84.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 11 omega   82.00  126.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  120.0000 44

#__ type_ start__ end____ width___ exp.time_
 12 omega   49.00   96.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000 -180.0000 47

#__ type_ start__ end____ width___ exp.time_
 13 omega   37.00   73.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000 -150.0000 36

#__ type_ start__ end____ width___ exp.time_
 14 omega   40.00   75.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  -30.0000 35

#__ type_ start__ end____ width___ exp.time_
 15 omega  152.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 16 omega   90.00  115.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000 -150.0000 25

#__ type_ start__ end____ width___ exp.time_
 17 omega  107.00  137.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000 -180.0000 30

#__ type_ start__ end____ width___ exp.time_
 18 omega   39.00   98.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  120.0000 59

#__ type_ start__ end____ width___ exp.time_
 19 omega   39.00   90.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000   30.0000 51

#__ type_ start__ end____ width___ exp.time_
 20 omega   83.00  116.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000   30.0000 33

#__ type_ start__ end____ width___ exp.time_
 21 omega   36.00   61.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000 -150.0000 25

#__ type_ start__ end____ width___ exp.time_
 22 omega   38.00   73.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   30.0000 35

#__ type_ start__ end____ width___ exp.time_
 23 omega   35.00   64.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  150.0000 29

#__ type_ start__ end____ width___ exp.time_
 24 omega   94.00  140.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000  -30.0000 46
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0577102000
_diffrn_orient_matrix_UB_12      -0.1040954000
_diffrn_orient_matrix_UB_13      0.0031545000
_diffrn_orient_matrix_UB_21      -0.0006701000
_diffrn_orient_matrix_UB_22      -0.0773714000
_diffrn_orient_matrix_UB_23      -0.0861153000
_diffrn_orient_matrix_UB_31      0.0379117000
_diffrn_orient_matrix_UB_32      -0.1600552000
_diffrn_orient_matrix_UB_33      0.0396454000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2259
_reflns_number_total             2738
_reflns_odcompleteness_completeness 93.30
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.95
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.629
_refine_diff_density_min         -0.383
_refine_diff_density_rms         0.098
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2738
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0379
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0556P)²+1.3991P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0933
_refine_ls_wR_factor_ref         0.1027
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C16(H16), C15(H15), C13(H13), C5(H5), C4(H4), C14(H14), C17(H17)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_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 0.690703(15) 1.29510(4) 0.567442(19) 0.02302(13) Uani 1 d . . .
F1 F 0.55762(9) 1.2898(3) 0.30587(11) 0.0280(5) Uani 1 d . . .
F2 F 0.63906(9) 1.1360(3) 0.33741(12) 0.0271(4) Uani 1 d . . .
F3 F 0.63604(9) 1.4049(3) 0.38266(11) 0.0257(4) Uani 1 d . . .
C1 C 0.58468(13) 1.1807(4) 0.44262(18) 0.0175(6) Uani 1 d . . .
H1 H 0.5596 1.2692 0.4630 0.021 Uiso 1 calc . . R
C11 C 0.55090(13) 1.0055(4) 0.42416(18) 0.0171(6) Uani 1 d . . .
C10 C 0.58150(13) 0.8724(4) 0.47510(17) 0.0165(6) Uani 1 d . . .
C2 C 0.63671(13) 1.1255(4) 0.51157(17) 0.0166(6) Uani 1 d . . .
C7 C 0.49939(13) 0.9668(4) 0.36596(18) 0.0185(6) Uani 1 d . . .
H7 H 0.4795 1.0566 0.3322 0.022 Uiso 1 calc . . R
C3 C 0.63511(13) 0.9517(4) 0.52957(17) 0.0172(6) Uani 1 d . . .
C16 C 0.77886(14) 0.7440(4) 0.6452(2) 0.0221(7) Uani 1 d . . .
H16 H 0.8193 0.7430 0.6432 0.026 Uiso 1 calc . . R
C15 C 0.75896(14) 0.6416(4) 0.70340(18) 0.0215(7) Uani 1 d . . .
H15 H 0.7858 0.5714 0.7400 0.026 Uiso 1 calc . . R
C13 C 0.65827(14) 0.7449(4) 0.65064(18) 0.0195(6) Uani 1 d . . .
H13 H 0.6178 0.7438 0.6524 0.023 Uiso 1 calc . . R
C5 C 0.50859(14) 0.6600(4) 0.41062(19) 0.0210(6) Uani 1 d . . .
H5 H 0.4942 0.5434 0.4061 0.025 Uiso 1 calc . . R
C4 C 0.56053(14) 0.6982(4) 0.46924(19) 0.0193(6) Uani 1 d . . .
H4 H 0.5805 0.6091 0.5034 0.023 Uiso 1 calc . . R
C14 C 0.69859(15) 0.6439(4) 0.70697(18) 0.0204(6) Uani 1 d . . .
H14 H 0.6852 0.5778 0.7470 0.024 Uiso 1 calc . . R
C6 C 0.47741(13) 0.7911(4) 0.35828(19) 0.0197(6) Uani 1 d . . .
C9 C 0.42272(14) 0.7472(5) 0.2935(2) 0.0255(7) Uani 1 d . . .
H9A H 0.3951 0.8454 0.2877 0.038 Uiso 1 calc . . GR
H9B H 0.4039 0.6421 0.3095 0.038 Uiso 1 calc . . GR
H9C H 0.4342 0.7260 0.2418 0.038 Uiso 1 calc . . GR
C8 C 0.60502(14) 1.2524(4) 0.36764(19) 0.0201(6) Uani 1 d . . .
C17 C 0.73908(14) 0.8489(4) 0.58944(18) 0.0189(6) Uani 1 d . . .
H17 H 0.7531 0.9190 0.5512 0.023 Uiso 1 calc . . R
C12 C 0.67811(14) 0.8486(4) 0.59113(18) 0.0172(6) Uani 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 C2 1.874(3) . ?
F1 C8 1.354(3) . ?
F2 C8 1.334(4) . ?
F3 C8 1.339(4) . ?
C1 C11 1.520(4) . ?
C1 C2 1.523(4) . ?
C1 C8 1.514(4) . ?
C11 C10 1.395(4) . ?
C11 C7 1.386(4) . ?
C10 C3 1.484(4) . ?
C10 C4 1.386(4) . ?
C2 C3 1.337(4) . ?
C7 C6 1.404(5) . ?
C3 C12 1.477(4) . ?
C16 C15 1.382(5) . ?
C16 C17 1.394(4) . ?
C15 C14 1.392(5) . ?
C13 C14 1.390(4) . ?
C13 C12 1.403(5) . ?
C5 C4 1.396(4) . ?
C5 C6 1.402(4) . ?
C6 C9 1.503(4) . ?
C17 C12 1.398(4) . ?

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
C11 C1 C2 101.5(2) . . ?
C8 C1 C11 111.7(3) . . ?
C8 C1 C2 112.8(3) . . ?
C10 C11 C1 109.0(2) . . ?
C7 C11 C1 129.9(3) . . ?
C7 C11 C10 121.1(3) . . ?
C11 C10 C3 109.1(3) . . ?
C4 C10 C11 120.5(3) . . ?
C4 C10 C3 130.4(3) . . ?
C1 C2 Br1 121.0(2) . . ?
C3 C2 Br1 126.5(2) . . ?
C3 C2 C1 112.2(3) . . ?
C11 C7 C6 119.6(3) . . ?
C2 C3 C10 108.1(3) . . ?
C2 C3 C12 128.2(3) . . ?
C12 C3 C10 123.7(3) . . ?
C15 C16 C17 120.8(3) . . ?
C16 C15 C14 119.7(3) . . ?
C14 C13 C12 120.5(3) . . ?
C4 C5 C6 122.3(3) . . ?
C10 C4 C5 118.2(3) . . ?
C13 C14 C15 120.0(3) . . ?
C7 C6 C9 119.8(3) . . ?
C5 C6 C7 118.3(3) . . ?
C5 C6 C9 121.8(3) . . ?
F1 C8 C1 111.2(3) . . ?
F2 C8 F1 106.7(2) . . ?
F2 C8 F3 107.5(3) . . ?
F2 C8 C1 112.3(3) . . ?
F3 C8 F1 105.8(2) . . ?
F3 C8 C1 113.0(3) . . ?
C16 C17 C12 119.9(3) . . ?
C13 C12 C3 120.6(3) . . ?
C17 C12 C3 120.4(3) . . ?
C17 C12 C13 119.0(3) . . ?

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 C2 C3 C10 174.2(2) . . . . ?
Br1 C2 C3 C12 -6.6(5) . . . . ?
C1 C11 C10 C3 1.0(3) . . . . ?
C1 C11 C10 C4 -178.6(3) . . . . ?
C1 C11 C7 C6 177.6(3) . . . . ?
C1 C2 C3 C10 -0.5(4) . . . . ?
C1 C2 C3 C12 178.7(3) . . . . ?
C11 C1 C2 Br1 -174.0(2) . . . . ?
C11 C1 C2 C3 1.1(3) . . . . ?
C11 C1 C8 F1 62.6(3) . . . . ?
C11 C1 C8 F2 -56.8(3) . . . . ?
C11 C1 C8 F3 -178.7(2) . . . . ?
C11 C10 C3 C2 -0.3(4) . . . . ?
C11 C10 C3 C12 -179.6(3) . . . . ?
C11 C10 C4 C5 0.6(5) . . . . ?
C11 C7 C6 C5 0.3(5) . . . . ?
C11 C7 C6 C9 -178.0(3) . . . . ?
C10 C11 C7 C6 0.3(5) . . . . ?
C10 C3 C12 C13 -53.8(4) . . . . ?
C10 C3 C12 C17 124.4(3) . . . . ?
C2 C1 C11 C10 -1.2(3) . . . . ?
C2 C1 C11 C7 -178.9(3) . . . . ?
C2 C1 C8 F1 176.2(2) . . . . ?
C2 C1 C8 F2 56.8(3) . . . . ?
C2 C1 C8 F3 -65.0(3) . . . . ?
C2 C3 C12 C13 127.2(4) . . . . ?
C2 C3 C12 C17 -54.7(5) . . . . ?
C7 C11 C10 C3 178.9(3) . . . . ?
C7 C11 C10 C4 -0.8(5) . . . . ?
C3 C10 C4 C5 -178.9(3) . . . . ?
C16 C15 C14 C13 1.8(5) . . . . ?
C16 C17 C12 C3 -176.8(3) . . . . ?
C16 C17 C12 C13 1.4(5) . . . . ?
C15 C16 C17 C12 -1.2(5) . . . . ?
C4 C10 C3 C2 179.3(3) . . . . ?
C4 C10 C3 C12 0.1(5) . . . . ?
C4 C5 C6 C7 -0.4(5) . . . . ?
C4 C5 C6 C9 177.9(3) . . . . ?
C14 C13 C12 C3 178.1(3) . . . . ?
C14 C13 C12 C17 -0.1(5) . . . . ?
C6 C5 C4 C10 -0.1(5) . . . . ?
C8 C1 C11 C10 119.2(3) . . . . ?
C8 C1 C11 C7 -58.4(4) . . . . ?
C8 C1 C2 Br1 66.3(3) . . . . ?
C8 C1 C2 C3 -118.6(3) . . . . ?
C17 C16 C15 C14 -0.5(5) . . . . ?
C12 C13 C14 C15 -1.5(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_a259
_database_code_depnum_ccdc_archive 'CCDC 1498726'
_audit_update_record             
;
2016-08-10 deposited with the CCDC.
2016-11-24 downloaded from the CCDC.
;
_audit_creation_date             2014-11-21
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C19 H17 Br Cl F3'
_chemical_formula_sum            'C19 H17 Br Cl F3'
_chemical_formula_weight         417.69
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C19 H17 F3 Cl1 Br1'
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   8.2233(3)
_cell_length_b                   22.8182(7)
_cell_length_c                   10.0565(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.447(4)
_cell_angle_gamma                90.00
_cell_volume                     1779.35(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4710
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.5300
_cell_measurement_theta_min      2.8990
_exptl_absorpt_coefficient_mu    2.487
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87103
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.559
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10596
_diffrn_reflns_theta_full        28.53
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.63
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.9987
_diffrn_measured_fraction_theta_max 0.8688
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -77.00   -3.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777  -77.0000   30.0000 74

#__ type_ start__ end____ width___ exp.time_
  2 omega  -48.00   -7.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8152  -57.0000 -120.0000 41

#__ type_ start__ end____ width___ exp.time_
  3 omega   70.00   95.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8152  178.0000   30.0000 25

#__ type_ start__ end____ width___ exp.time_
  4 omega  -26.00   49.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8152  -77.0000  150.0000 75

#__ type_ start__ end____ width___ exp.time_
  5 omega  -90.00  -63.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777  -38.0000 -150.0000 27

#__ type_ start__ end____ width___ exp.time_
  6 omega   -6.00   23.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777  -99.0000  -90.0000 29

#__ type_ start__ end____ width___ exp.time_
  7 omega  -36.00   -8.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777  -38.0000 -150.0000 28
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0449597000
_diffrn_orient_matrix_UB_12      0.0246723000
_diffrn_orient_matrix_UB_13      0.0129871000
_diffrn_orient_matrix_UB_21      0.0204133000
_diffrn_orient_matrix_UB_22      -0.0087924000
_diffrn_orient_matrix_UB_23      0.0713490000
_diffrn_orient_matrix_UB_31      0.0770362000
_diffrn_orient_matrix_UB_32      0.0167374000
_diffrn_orient_matrix_UB_33      0.0182957000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3444
_reflns_number_total             3970
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3970
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0347
_refine_ls_R_factor_gt           0.0266
_refine_ls_restrained_S_all      1.011
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0290P)²+0.5907P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0598
_refine_ls_wR_factor_ref         0.0631
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.14132(2) 0.348031(9) 0.322358(18) 0.02204(7) Uani 1 1 d . . .
C16 C 0.5785(2) 0.39146(8) 0.81780(18) 0.0156(4) Uani 1 1 d . . .
H16 H 0.6534 0.3887 0.7663 0.019 Uiso 1 1 calc R . .
C5 C 0.4981(2) 0.31049(8) 0.57877(17) 0.0148(4) Uani 1 1 d . . .
C6 C 0.5448(2) 0.25382(8) 0.62822(19) 0.0192(4) Uani 1 1 d . . .
H6 H 0.4825 0.2345 0.6770 0.023 Uiso 1 1 calc R . .
C11 C 0.4121(2) 0.36946(8) 0.75930(18) 0.0148(4) Uani 1 1 d . . .
C4 C 0.3521(2) 0.34112(8) 0.61284(18) 0.0157(4) Uani 1 1 d . . .
H4 H 0.2679 0.3109 0.6137 0.019 Uiso 1 1 calc R . .
C3 C 0.2594(2) 0.38479(8) 0.49843(18) 0.0155(4) Uani 1 1 d . . .
C2 C 0.2594(2) 0.44223(8) 0.51368(18) 0.0170(4) Uani 1 1 d . . .
H2 H 0.3188 0.4568 0.6031 0.020 Uiso 1 1 calc R . .
C15 C 0.6372(2) 0.41755(8) 0.95067(19) 0.0172(4) Uani 1 1 d . . .
C13 C 0.3584(3) 0.39884(8) 0.97006(19) 0.0213(4) Uani 1 1 d . . .
H13 H 0.2841 0.4012 1.0223 0.026 Uiso 1 1 calc R . .
C14 C 0.5251(2) 0.41993(8) 1.02968(18) 0.0189(4) Uani 1 1 d . . .
C10 C 0.5910(2) 0.33842(8) 0.50409(19) 0.0167(4) Uani 1 1 d . . .
H10 H 0.5599 0.3760 0.4693 0.020 Uiso 1 1 calc R . .
C12 C 0.2968(2) 0.37429(8) 0.83551(19) 0.0179(4) Uani 1 1 d . . .
F2 F 0.00190(14) 0.48153(5) 0.35226(11) 0.0257(3) Uani 1 1 d . . .
F1 F 0.20836(15) 0.54088(5) 0.45436(13) 0.0319(3) Uani 1 1 d . . .
F3 F 0.22763(16) 0.48343(6) 0.29020(12) 0.0344(3) Uani 1 1 d . . .
C9 C 0.7293(2) 0.31086(8) 0.48085(18) 0.0184(4) Uani 1 1 d . . .
H9 H 0.7912 0.3298 0.4312 0.022 Uiso 1 1 calc R . .
C1 C 0.1745(2) 0.48620(8) 0.4031(2) 0.0208(4) Uani 1 1 d . . .
C17 C 0.1127(3) 0.35386(9) 0.7744(2) 0.0254(4) Uani 1 1 d . . .
H17A H 0.0603 0.3711 0.6830 0.038 Uiso 1 1 calc R . .
H17B H 0.0501 0.3655 0.8354 0.038 Uiso 1 1 calc R . .
H17C H 0.1102 0.3119 0.7658 0.038 Uiso 1 1 calc R . .
C7 C 0.6830(2) 0.22575(8) 0.6057(2) 0.0213(4) Uani 1 1 d . . .
H7 H 0.7139 0.1880 0.6393 0.026 Uiso 1 1 calc R . .
C18 C 0.5848(3) 0.44483(9) 1.1779(2) 0.0267(4) Uani 1 1 d . . .
H18A H 0.6817 0.4227 1.2361 0.040 Uiso 1 1 calc R . .
H18B H 0.4925 0.4426 1.2162 0.040 Uiso 1 1 calc R . .
H18C H 0.6181 0.4850 1.1753 0.040 Uiso 1 1 calc R . .
C8 C 0.7741(2) 0.25493(8) 0.53231(19) 0.0177(4) Uani 1 1 d . . .
C19 C 0.8179(2) 0.44177(9) 1.0080(2) 0.0228(4) Uani 1 1 d . . .
H19A H 0.8812 0.4212 1.0927 0.034 Uiso 1 1 calc R . .
H19B H 0.8132 0.4827 1.0286 0.034 Uiso 1 1 calc R . .
H19C H 0.8744 0.4369 0.9391 0.034 Uiso 1 1 calc R . .
Cl1 Cl 0.94824(6) 0.22013(2) 0.50320(5) 0.02578(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 C3 1.9071(17) . ?
C16 H16 0.9300 . ?
C16 C11 1.391(2) . ?
C16 C15 1.394(2) . ?
C5 C6 1.393(3) . ?
C5 C4 1.524(2) . ?
C5 C10 1.391(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.387(3) . ?
C11 C4 1.532(2) . ?
C11 C12 1.408(2) . ?
C4 H4 0.9800 . ?
C4 C3 1.521(3) . ?
C3 C2 1.320(3) . ?
C2 H2 0.9300 . ?
C2 C1 1.488(3) . ?
C15 C14 1.404(3) . ?
C15 C19 1.509(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.387(3) . ?
C13 C12 1.395(3) . ?
C14 C18 1.516(2) . ?
C10 H10 0.9300 . ?
C10 C9 1.386(2) . ?
C12 C17 1.506(3) . ?
F2 C1 1.343(2) . ?
F1 C1 1.343(2) . ?
F3 C1 1.347(2) . ?
C9 H9 0.9300 . ?
C9 C8 1.380(3) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C7 H7 0.9300 . ?
C7 C8 1.385(3) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C8 Cl1 1.7455(18) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 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
C11 C16 H16 118.7 . . ?
C11 C16 C15 122.52(16) . . ?
C15 C16 H16 118.7 . . ?
C6 C5 C4 119.33(15) . . ?
C10 C5 C6 118.84(16) . . ?
C10 C5 C4 121.78(16) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 C5 120.92(16) . . ?
C7 C6 H6 119.5 . . ?
C16 C11 C4 121.05(15) . . ?
C16 C11 C12 119.16(16) . . ?
C12 C11 C4 119.79(16) . . ?
C5 C4 C11 112.58(14) . . ?
C5 C4 H4 106.9 . . ?
C5 C4 C3 111.36(14) . . ?
C11 C4 H4 106.9 . . ?
C3 C4 C11 111.76(15) . . ?
C3 C4 H4 106.9 . . ?
C4 C3 Br1 112.72(12) . . ?
C2 C3 Br1 121.66(14) . . ?
C2 C3 C4 125.61(16) . . ?
C3 C2 H2 116.5 . . ?
C3 C2 C1 126.95(17) . . ?
C1 C2 H2 116.5 . . ?
C16 C15 C14 118.42(17) . . ?
C16 C15 C19 120.34(16) . . ?
C14 C15 C19 121.23(17) . . ?
C14 C13 H13 118.5 . . ?
C14 C13 C12 123.09(16) . . ?
C12 C13 H13 118.5 . . ?
C15 C14 C18 120.80(17) . . ?
C13 C14 C15 118.86(17) . . ?
C13 C14 C18 120.35(17) . . ?
C5 C10 H10 119.6 . . ?
C5 C10 C9 120.80(17) . . ?
C9 C10 H10 119.6 . . ?
C11 C12 C17 121.42(16) . . ?
C13 C12 C11 117.86(17) . . ?
C13 C12 C17 120.72(16) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 C10 119.20(16) . . ?
C8 C9 H9 120.4 . . ?
F2 C1 C2 113.83(15) . . ?
F2 C1 F1 106.10(15) . . ?
F2 C1 F3 105.89(15) . . ?
F1 C1 C2 110.71(16) . . ?
F1 C1 F3 106.46(15) . . ?
F3 C1 C2 113.29(15) . . ?
C12 C17 H17A 109.5 . . ?
C12 C17 H17B 109.5 . . ?
C12 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C6 C7 H7 120.6 . . ?
C8 C7 C6 118.89(17) . . ?
C8 C7 H7 120.6 . . ?
C14 C18 H18A 109.5 . . ?
C14 C18 H18B 109.5 . . ?
C14 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C9 C8 C7 121.34(17) . . ?
C9 C8 Cl1 119.28(14) . . ?
C7 C8 Cl1 119.37(15) . . ?
C15 C19 H19A 109.5 . . ?
C15 C19 H19B 109.5 . . ?
C15 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

