# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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. 
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#######################################################################

data_testall_a
_database_code_depnum_ccdc_archive 'CCDC 1839159'
_audit_update_record             
;
2018-04-24 deposited with the CCDC.
2018-07-04 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H31 B Br2 F5 N'
_chemical_formula_sum            'C26 H31 B Br2 F5 N'
_chemical_formula_weight         623.15

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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   11.6404(4)
_cell_length_b                   15.7259(5)
_cell_length_c                   14.2888(5)
_cell_angle_alpha                90
_cell_angle_beta                 99.812(2)
_cell_angle_gamma                90
_cell_volume                     2577.39(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9904
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      28.40


_exptl_special_details           
;
The crystal was immersed in a film of perfluoropolyether oil, mounted on a 
glass fiber and transferred to stream of cold nitrogen.
;
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.606
_exptl_crystal_F_000             1256
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    3.197
_shelx_estimated_absorpt_T_min   0.447
_shelx_estimated_absorpt_T_max   0.740
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3795
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SadAbs 2014/5 (Bruker AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker SMART-APEX'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector                 'CCD area detector (Apex1)'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            33039
_diffrn_reflns_av_unetI/netI     0.0413
_diffrn_reflns_av_R_equivalents  0.0535
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.941
_diffrn_reflns_theta_max         28.405
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6463
_reflns_number_gt                5544
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Smart NT ver. 5.63 (Bruker AXS)'
_computing_cell_refinement       'Saint+ ver. V8.37A (Bruker AXS)'
_computing_data_reduction        'Saint+ ver. V8.37A (Bruker AXS)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_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     
'w=1/[σ²(Fo²)+(0.0437P)²+0.4906P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6463
_refine_ls_number_parameters     324
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0311
_refine_ls_wR_factor_ref         0.0784
_refine_ls_wR_factor_gt          0.0748
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.75384(2) 0.12878(2) 0.51092(2) 0.01626(6) Uani 1 1 d . . . . .
F1 F 0.71051(10) 0.41863(7) 0.57312(9) 0.0157(2) Uani 1 1 d . . . . .
N1 N 0.50660(14) 0.28716(10) 0.58894(11) 0.0102(3) Uani 1 1 d . . . . .
C1 C 0.82993(17) 0.29567(12) 0.60433(14) 0.0122(4) Uani 1 1 d . . . . .
B1 B 0.72279(19) 0.22800(14) 0.59612(16) 0.0122(4) Uani 1 1 d . . . . .
C2 C 0.81796(17) 0.38323(12) 0.59294(14) 0.0129(4) Uani 1 1 d . . . . .
Br2 Br 0.73306(2) 0.17765(2) 0.72941(2) 0.01301(6) Uani 1 1 d . . . . .
F2 F 0.89040(11) 0.52353(7) 0.58653(10) 0.0213(3) Uani 1 1 d . . . . .
C3 C 0.90996(18) 0.44003(12) 0.60079(15) 0.0149(4) Uani 1 1 d . . . . .
F3 F 1.11334(10) 0.46388(8) 0.63475(10) 0.0215(3) Uani 1 1 d . . . . .
F4 F 1.14866(10) 0.29540(8) 0.67024(9) 0.0190(3) Uani 1 1 d . . . . .
C4 C 1.02238(17) 0.41039(13) 0.62563(15) 0.0150(4) Uani 1 1 d . . . . .
C5 C 1.04003(17) 0.32463(13) 0.64182(15) 0.0138(4) Uani 1 1 d . . . . .
F5 F 0.97309(11) 0.18746(7) 0.64760(9) 0.0178(3) Uani 1 1 d . . . . .
C6 C 0.94613(17) 0.26967(12) 0.63025(14) 0.0131(4) Uani 1 1 d . . . . .
C7 C 0.59612(16) 0.26859(11) 0.54818(14) 0.0108(4) Uani 1 1 d . . . . .
C8 C 0.56487(17) 0.29083(12) 0.44142(14) 0.0128(4) Uani 1 1 d . . . . .
C9 C 0.47072(17) 0.35890(12) 0.44294(15) 0.0139(4) Uani 1 1 d . . . . .
H9A H 0.5060 0.4147 0.4537 0.017 Uiso 1 1 calc R U . . .
H9B H 0.4171 0.3597 0.3830 0.017 Uiso 1 1 calc R U . . .
C10 C 0.40693(17) 0.33506(12) 0.52394(14) 0.0125(4) Uani 1 1 d . . . . .
C11 C 0.66230(19) 0.32347(14) 0.39053(15) 0.0180(4) Uani 1 1 d . . . . .
H11A H 0.6320 0.3314 0.3243 0.027 Uiso 1 1 calc R U . . .
H11B H 0.7246 0.2827 0.3975 0.027 Uiso 1 1 calc R U . . .
H11C H 0.6912 0.3766 0.4180 0.027 Uiso 1 1 calc R U . . .
C12 C 0.51345(18) 0.20984(13) 0.38648(14) 0.0158(4) Uani 1 1 d . . . . .
H12A H 0.4550 0.2263 0.3338 0.024 Uiso 1 1 calc R U . . .
H12B H 0.4790 0.1738 0.4284 0.024 Uiso 1 1 calc R U . . .
H12C H 0.5746 0.1796 0.3635 0.024 Uiso 1 1 calc R U . . .
C13 C 0.30017(17) 0.27896(13) 0.49335(15) 0.0151(4) Uani 1 1 d . . . . .
H13A H 0.2400 0.3116 0.4552 0.023 Uiso 1 1 calc R U . . .
H13B H 0.2724 0.2582 0.5486 0.023 Uiso 1 1 calc R U . . .
H13C H 0.3210 0.2318 0.4570 0.023 Uiso 1 1 calc R U . . .
C14 C 0.36871(18) 0.41210(12) 0.57497(15) 0.0159(4) Uani 1 1 d . . . . .
H14A H 0.3065 0.4406 0.5342 0.024 Uiso 1 1 calc R U . . .
H14B H 0.4333 0.4503 0.5912 0.024 Uiso 1 1 calc R U . . .
H14C H 0.3421 0.3941 0.6318 0.024 Uiso 1 1 calc R U . . .
C15 C 0.49063(16) 0.26481(12) 0.68606(14) 0.0110(4) Uani 1 1 d . . . . .
C16 C 0.44066(17) 0.18535(12) 0.69959(15) 0.0127(4) Uani 1 1 d . . . . .
C17 C 0.42648(18) 0.16477(13) 0.79206(15) 0.0164(4) Uani 1 1 d . . . . .
H17 H 0.3932 0.1128 0.8033 0.020 Uiso 1 1 calc R U . . .
C18 C 0.46066(19) 0.21971(14) 0.86739(15) 0.0181(4) Uani 1 1 d . . . . .
H18 H 0.4517 0.2041 0.9285 0.022 Uiso 1 1 calc R U . . .
C19 C 0.50812(18) 0.29764(13) 0.85140(15) 0.0165(4) Uani 1 1 d . . . . .
H19 H 0.5297 0.3345 0.9023 0.020 Uiso 1 1 calc R U . . .
C20 C 0.52467(17) 0.32269(12) 0.76085(15) 0.0127(4) Uani 1 1 d . . . . .
C21 C 0.40509(18) 0.11838(12) 0.62288(15) 0.0141(4) Uani 1 1 d . . . . .
H21 H 0.4107 0.1442 0.5614 0.017 Uiso 1 1 calc R U . . .
C22 C 0.48582(19) 0.04096(13) 0.63620(16) 0.0194(4) Uani 1 1 d . . . . .
H22A H 0.4586 -0.0007 0.5885 0.029 Uiso 1 1 calc R U . . .
H22B H 0.4860 0.0169 0.6980 0.029 Uiso 1 1 calc R U . . .
H22C H 0.5635 0.0581 0.6305 0.029 Uiso 1 1 calc R U . . .
C23 C 0.27792(19) 0.08923(14) 0.61972(17) 0.0212(4) Uani 1 1 d . . . . .
H23A H 0.2536 0.0557 0.5637 0.032 Uiso 1 1 calc R U . . .
H23B H 0.2283 0.1381 0.6185 0.032 Uiso 1 1 calc R U . . .
H23C H 0.2727 0.0557 0.6750 0.032 Uiso 1 1 calc R U . . .
C24 C 0.58316(18) 0.40814(12) 0.75211(15) 0.0155(4) Uani 1 1 d . . . . .
H24 H 0.5842 0.4186 0.6846 0.019 Uiso 1 1 calc R U . . .
C25 C 0.5166(2) 0.48142(14) 0.78984(17) 0.0224(5) Uani 1 1 d . . . . .
H25A H 0.5515 0.5346 0.7772 0.034 Uiso 1 1 calc R U . . .
H25B H 0.5201 0.4749 0.8571 0.034 Uiso 1 1 calc R U . . .
H25C H 0.4367 0.4805 0.7588 0.034 Uiso 1 1 calc R U . . .
C26 C 0.70992(19) 0.40832(14) 0.80483(16) 0.0197(4) Uani 1 1 d . . . . .
H26A H 0.7466 0.4610 0.7930 0.030 Uiso 1 1 calc R U . . .
H26B H 0.7516 0.3619 0.7826 0.030 Uiso 1 1 calc R U . . .
H26C H 0.7107 0.4022 0.8718 0.030 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 B1 2.049(2) . ?
F1 C2 1.354(2) . ?
N1 C7 1.310(2) . ?
N1 C15 1.474(2) . ?
N1 C10 1.552(2) . ?
C1 C2 1.391(3) . ?
C1 C6 1.401(3) . ?
C1 B1 1.628(3) . ?
B1 C7 1.645(3) . ?
B1 Br2 2.047(2) . ?
C2 C3 1.384(3) . ?
F2 C3 1.342(2) . ?
C3 C4 1.377(3) . ?
F3 C4 1.341(2) . ?
F4 C5 1.342(2) . ?
C4 C5 1.378(3) . ?
C5 C6 1.381(3) . ?
F5 C6 1.343(2) . ?
C7 C8 1.547(3) . ?
C8 C9 1.535(3) . ?
C8 C11 1.536(3) . ?
C8 C12 1.561(3) . ?
C9 C10 1.525(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C14 1.519(3) . ?
C10 C13 1.526(3) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.405(3) . ?
C15 C20 1.408(3) . ?
C16 C17 1.397(3) . ?
C16 C21 1.525(3) . ?
C17 C18 1.385(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.379(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.397(3) . ?
C19 H19 0.9300 . ?
C20 C24 1.521(3) . ?
C21 C22 1.530(3) . ?
C21 C23 1.543(3) . ?
C21 H21 0.9800 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 C25 1.536(3) . ?
C24 C26 1.538(3) . ?
C24 H24 0.9800 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 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
C7 N1 C15 127.07(16) . . ?
C7 N1 C10 114.34(16) . . ?
C15 N1 C10 118.54(15) . . ?
C2 C1 C6 113.13(18) . . ?
C2 C1 B1 125.34(17) . . ?
C6 C1 B1 121.42(17) . . ?
C1 B1 C7 113.42(16) . . ?
C1 B1 Br2 105.26(13) . . ?
C7 B1 Br2 116.33(14) . . ?
C1 B1 Br1 109.26(13) . . ?
C7 B1 Br1 106.52(13) . . ?
Br2 B1 Br1 105.67(10) . . ?
F1 C2 C3 115.21(17) . . ?
F1 C2 C1 120.13(17) . . ?
C3 C2 C1 124.66(18) . . ?
F2 C3 C4 119.96(18) . . ?
F2 C3 C2 120.66(18) . . ?
C4 C3 C2 119.37(18) . . ?
F3 C4 C3 120.82(18) . . ?
F3 C4 C5 120.33(18) . . ?
C3 C4 C5 118.85(18) . . ?
F4 C5 C4 119.47(18) . . ?
F4 C5 C6 120.51(17) . . ?
C4 C5 C6 120.00(18) . . ?
F5 C6 C5 115.14(17) . . ?
F5 C6 C1 120.95(17) . . ?
C5 C6 C1 123.90(18) . . ?
N1 C7 C8 108.46(16) . . ?
N1 C7 B1 128.72(17) . . ?
C8 C7 B1 122.81(16) . . ?
C9 C8 C11 111.12(16) . . ?
C9 C8 C7 101.09(15) . . ?
C11 C8 C7 118.29(16) . . ?
C9 C8 C12 111.27(16) . . ?
C11 C8 C12 106.58(16) . . ?
C7 C8 C12 108.48(15) . . ?
C10 C9 C8 106.29(15) . . ?
C10 C9 H9A 110.5 . . ?
C8 C9 H9A 110.5 . . ?
C10 C9 H9B 110.5 . . ?
C8 C9 H9B 110.5 . . ?
H9A C9 H9B 108.7 . . ?
C14 C10 C9 112.87(16) . . ?
C14 C10 C13 107.91(16) . . ?
C9 C10 C13 113.76(17) . . ?
C14 C10 N1 110.49(16) . . ?
C9 C10 N1 99.35(15) . . ?
C13 C10 N1 112.34(15) . . ?
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 . . ?
C8 C12 H12A 109.5 . . ?
C8 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C8 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C10 C14 H14A 109.5 . . ?
C10 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C10 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C20 122.67(18) . . ?
C16 C15 N1 117.59(17) . . ?
C20 C15 N1 119.73(17) . . ?
C17 C16 C15 117.03(18) . . ?
C17 C16 C21 117.27(18) . . ?
C15 C16 C21 125.66(18) . . ?
C18 C17 C16 121.73(19) . . ?
C18 C17 H17 119.1 . . ?
C16 C17 H17 119.1 . . ?
C19 C18 C17 119.72(19) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C18 C19 C20 121.76(19) . . ?
C18 C19 H19 119.1 . . ?
C20 C19 H19 119.1 . . ?
C19 C20 C15 117.07(18) . . ?
C19 C20 C24 117.36(18) . . ?
C15 C20 C24 125.50(18) . . ?
C16 C21 C22 111.98(17) . . ?
C16 C21 C23 111.58(17) . . ?
C22 C21 C23 109.45(17) . . ?
C16 C21 H21 107.9 . . ?
C22 C21 H21 107.9 . . ?
C23 C21 H21 107.9 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C20 C24 C25 111.98(17) . . ?
C20 C24 C26 111.52(17) . . ?
C25 C24 C26 109.00(17) . . ?
C20 C24 H24 108.1 . . ?
C25 C24 H24 108.1 . . ?
C26 C24 H24 108.1 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C24 C26 H26A 109.5 . . ?
C24 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C24 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?

_refine_diff_density_max         1.642
_refine_diff_density_min         -0.454
_refine_diff_density_rms         0.091

####################################################################### 
# 
# 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_ToTh069_a
_database_code_depnum_ccdc_archive 'CCDC 1839162'
_audit_update_record             
;
2018-04-24 deposited with the CCDC.
2018-07-04 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H28 B Br2 Cl0 F5 N2 O2'
_chemical_formula_sum            'C30 H28 B Br2 Cl0 F5 N2 O2'
_chemical_formula_weight         714.17

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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   8.492(5)
_cell_length_b                   15.351(7)
_cell_length_c                   22.229(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2898(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    2471
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      21.92


_exptl_special_details           
;
The crystal was immersed in a film of perfluoropolyether oil, mounted on a 
polyimide microloop (MicroMounts of MiTeGen) and transferred to stream of cold 
nitrogen (Oxford Cryostream 700).
;
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.637
_exptl_crystal_F_000             1432
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.444
_exptl_crystal_size_mid          0.286
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    2.862
_shelx_estimated_absorpt_T_min   0.363
_shelx_estimated_absorpt_T_max   0.673
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4692
_exptl_absorpt_correction_T_max  0.5950
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2.00 0.00 1.00 0.0950
2.00 0.00 -1.00 0.1310
-1.00 0.00 -1.00 0.1150
1.00 0.00 1.00 0.1320
-2.00 1.00 1.00 0.0830
2.00 -1.00 -1.00 0.1380
-1.00 1.00 2.00 0.0380
1.00 -1.00 -2.00 0.1570
-1.00 2.00 2.00 0.0400
1.00 -2.00 -2.00 0.1580
-1.00 2.00 -1.00 0.0860
1.00 -2.00 1.00 0.1310
0.00 1.00 2.00 0.0590
0.00 -1.00 -2.00 0.1960
0.00 1.00 1.00 0.0400
0.00 -1.00 -1.00 0.1700
1.00 9.00 -2.00 0.0500
-1.00 -9.00 3.00 0.0750

_exptl_absorpt_process_details   'SadAbs 2014/5 (Bruker AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      103(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'multi-layer mirror'
_diffrn_source                   'rotating-anode (Nonius FR-591)'
_diffrn_measurement_device_type  'Bruker X8-APEX II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector                 'CCD area detector (Apex2)'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            17218
_diffrn_reflns_av_unetI/netI     0.0929
_diffrn_reflns_av_R_equivalents  0.0699
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.262
_diffrn_reflns_theta_max         26.022
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5708
_reflns_number_gt                4666
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.765
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 ver. 2014.9 (Bruker AXS)'
_computing_cell_refinement       'Saint+ ver. V8.34A (Bruker AXS)'
_computing_data_reduction        'Saint+ ver. V8.34A (Bruker AXS)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_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     'w=1/[σ²(Fo²)] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1747 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.017(8)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5708
_refine_ls_number_parameters     387
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0381
_refine_ls_wR_factor_ref         0.0838
_refine_ls_wR_factor_gt          0.0768
_refine_ls_goodness_of_fit_ref   0.937
_refine_ls_restrained_S_all      0.937
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2768(7) 0.2956(4) 0.3030(2) 0.0119(13) Uani 1 1 d . . . . .
N2 N 0.2315(6) 0.2623(3) 0.3578(2) 0.0112(11) Uani 1 1 d . . . . .
C3 C 0.2138(8) 0.3171(4) 0.4120(2) 0.0134(13) Uani 1 1 d . . . . .
C4 C 0.3480(8) 0.3329(4) 0.4460(2) 0.0148(13) Uani 1 1 d . . . . .
C5 C 0.3324(9) 0.3848(4) 0.4965(2) 0.0199(14) Uani 1 1 d . . . . .
H5 H 0.4231 0.3980 0.5198 0.024 Uiso 1 1 calc R U . . .
C6 C 0.1874(9) 0.4180(4) 0.5140(2) 0.0215(16) Uani 1 1 d . . . . .
C7 C 0.0549(8) 0.3948(4) 0.4817(3) 0.0211(14) Uani 1 1 d . . . . .
H7 H -0.0448 0.4157 0.4945 0.025 Uiso 1 1 calc R U . . .
C8 C 0.0626(8) 0.3414(4) 0.4308(3) 0.0156(14) Uani 1 1 d . . . . .
C9 C 0.5049(8) 0.2923(4) 0.4315(3) 0.0209(14) Uani 1 1 d . . . . .
H9A H 0.5832 0.3113 0.4611 0.031 Uiso 1 1 calc R U . . .
H9B H 0.5382 0.3106 0.3912 0.031 Uiso 1 1 calc R U . . .
H9C H 0.4954 0.2287 0.4327 0.031 Uiso 1 1 calc R U . . .
C10 C 0.1749(10) 0.4740(5) 0.5697(3) 0.0354(19) Uani 1 1 d . . . . .
H10A H 0.0671 0.4960 0.5735 0.053 Uiso 1 1 calc R U . . .
H10B H 0.2481 0.5231 0.5664 0.053 Uiso 1 1 calc R U . . .
H10C H 0.2015 0.4391 0.6052 0.053 Uiso 1 1 calc R U . . .
C11 C -0.0867(8) 0.3085(4) 0.4038(3) 0.0209(15) Uani 1 1 d . . . . .
H11A H -0.1496 0.3577 0.3894 0.031 Uiso 1 1 calc R U . . .
H11B H -0.1465 0.2763 0.4343 0.031 Uiso 1 1 calc R U . . .
H11C H -0.0622 0.2697 0.3701 0.031 Uiso 1 1 calc R U . . .
C12 C 0.2090(7) 0.1710(4) 0.3702(3) 0.0150(13) Uani 1 1 d . . . . .
C14 C 0.1941(7) 0.1125(4) 0.3166(2) 0.0156(13) Uani 1 1 d . . . . .
O13 O 0.1954(6) 0.1477(3) 0.42157(18) 0.0214(10) Uani 1 1 d . . . . .
C15 C 0.0213(8) 0.1212(4) 0.2945(3) 0.0217(14) Uani 1 1 d . . . . .
H15A H 0.0053 0.0839 0.2593 0.032 Uiso 1 1 calc R U . . .
H15B H 0.0002 0.1820 0.2837 0.032 Uiso 1 1 calc R U . . .
H15C H -0.0505 0.1033 0.3267 0.032 Uiso 1 1 calc R U . . .
C16 C 0.2339(8) 0.0192(4) 0.3329(3) 0.0192(14) Uani 1 1 d . . . . .
H16A H 0.2289 -0.0172 0.2968 0.029 Uiso 1 1 calc R U . . .
H16B H 0.1581 -0.0023 0.3627 0.029 Uiso 1 1 calc R U . . .
H16C H 0.3403 0.0168 0.3498 0.029 Uiso 1 1 calc R U . . .
C17 C 0.2950(8) 0.1437(4) 0.2659(3) 0.0163(14) Uani 1 1 d . . . . .
O18 O 0.3493(6) 0.0971(3) 0.22777(18) 0.0252(10) Uani 1 1 d . . . . .
N19 N 0.3153(6) 0.2373(3) 0.25970(19) 0.0141(11) Uani 1 1 d . . . . .
C20 C 0.3968(8) 0.2607(4) 0.2039(2) 0.0159(14) Uani 1 1 d . . . . .
C21 C 0.3125(8) 0.2671(4) 0.1510(3) 0.0165(14) Uani 1 1 d . . . . .
C22 C 0.3977(8) 0.2910(4) 0.0996(3) 0.0215(16) Uani 1 1 d . . . . .
H22 H 0.3428 0.2981 0.0627 0.026 Uiso 1 1 calc R U . . .
C23 C 0.5576(9) 0.3045(4) 0.1006(3) 0.0251(17) Uani 1 1 d . . . . .
C24 C 0.6377(9) 0.2896(4) 0.1540(3) 0.0216(15) Uani 1 1 d . . . . .
H24 H 0.7490 0.2960 0.1548 0.026 Uiso 1 1 calc R U . . .
C25 C 0.5604(7) 0.2657(4) 0.2062(3) 0.0174(14) Uani 1 1 d . . . . .
C26 C 0.1392(9) 0.2508(4) 0.1474(3) 0.0260(16) Uani 1 1 d . . . . .
H26A H 0.1020 0.2633 0.1066 0.039 Uiso 1 1 calc R U . . .
H26B H 0.0844 0.2887 0.1761 0.039 Uiso 1 1 calc R U . . .
H26C H 0.1175 0.1897 0.1573 0.039 Uiso 1 1 calc R U . . .
C27 C 0.6452(10) 0.3332(4) 0.0447(3) 0.0306(17) Uani 1 1 d . . . . .
H27A H 0.7560 0.3158 0.0478 0.046 Uiso 1 1 calc R U . . .
H27B H 0.6385 0.3967 0.0407 0.046 Uiso 1 1 calc R U . . .
H27C H 0.5980 0.3057 0.0092 0.046 Uiso 1 1 calc R U . . .
C28 C 0.6528(8) 0.2430(4) 0.2622(3) 0.0218(15) Uani 1 1 d . . . . .
H28A H 0.7610 0.2645 0.2582 0.033 Uiso 1 1 calc R U . . .
H28B H 0.6544 0.1796 0.2674 0.033 Uiso 1 1 calc R U . . .
H28C H 0.6031 0.2701 0.2973 0.033 Uiso 1 1 calc R U . . .
B29 B 0.2571(8) 0.4030(5) 0.2914(3) 0.0187(16) Uani 1 1 d . . . . .
Br30 Br 0.01911(7) 0.39762(4) 0.27589(3) 0.01953(16) Uani 1 1 d . . . . .
Br31 Br 0.34768(8) 0.45742(4) 0.21593(2) 0.01928(16) Uani 1 1 d . . . . .
C32 C 0.3156(8) 0.4687(4) 0.3438(2) 0.0145(13) Uani 1 1 d . . . . .
C33 C 0.4757(8) 0.4746(4) 0.3559(2) 0.0159(13) Uani 1 1 d . . . . .
C34 C 0.5420(8) 0.5279(4) 0.3987(3) 0.0225(15) Uani 1 1 d . . . . .
C35 C 0.4456(9) 0.5802(4) 0.4321(3) 0.0235(17) Uani 1 1 d . . . . .
C36 C 0.2887(9) 0.5800(4) 0.4207(3) 0.0243(17) Uani 1 1 d . . . . .
C37 C 0.2244(8) 0.5261(4) 0.3775(3) 0.0195(14) Uani 1 1 d . . . . .
F38 F 0.5760(4) 0.4229(2) 0.32432(15) 0.0232(9) Uani 1 1 d . . . . .
F39 F 0.6974(5) 0.5267(3) 0.40836(17) 0.0327(10) Uani 1 1 d . . . . .
F40 F 0.5051(6) 0.6295(2) 0.47654(15) 0.0365(11) Uani 1 1 d . . . . .
F41 F 0.1918(6) 0.6326(2) 0.45334(16) 0.0329(11) Uani 1 1 d . . . . .
F42 F 0.0671(4) 0.5317(2) 0.37045(15) 0.0243(9) 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
C1 N19 1.355(7) . ?
C1 N2 1.375(7) . ?
C1 B29 1.676(9) . ?
N2 C12 1.441(7) . ?
N2 C3 1.476(7) . ?
C3 C4 1.390(9) . ?
C3 C8 1.401(9) . ?
C4 C5 1.383(9) . ?
C4 C9 1.505(9) . ?
C5 C6 1.389(10) . ?
C5 H5 0.9500 . ?
C6 C7 1.382(10) . ?
C6 C10 1.509(8) . ?
C7 C8 1.398(9) . ?
C7 H7 0.9500 . ?
C8 C11 1.491(9) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 O13 1.201(7) . ?
C12 C14 1.498(8) . ?
C14 C17 1.496(8) . ?
C14 C16 1.515(8) . ?
C14 C15 1.553(9) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 O18 1.201(7) . ?
C17 N19 1.454(8) . ?
N19 C20 1.465(7) . ?
C20 C21 1.380(8) . ?
C20 C25 1.392(9) . ?
C21 C22 1.401(9) . ?
C21 C26 1.496(10) . ?
C22 C23 1.374(10) . ?
C22 H22 0.9500 . ?
C23 C24 1.388(10) . ?
C23 C27 1.515(9) . ?
C24 C25 1.382(9) . ?
C24 H24 0.9500 . ?
C25 C28 1.512(8) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
B29 C32 1.619(9) . ?
B29 Br31 2.025(7) . ?
B29 Br30 2.052(7) . ?
C32 C37 1.393(9) . ?
C32 C33 1.389(9) . ?
C33 F38 1.359(7) . ?
C33 C34 1.377(9) . ?
C34 F39 1.337(8) . ?
C34 C35 1.365(10) . ?
C35 F40 1.344(7) . ?
C35 C36 1.357(10) . ?
C36 F41 1.362(8) . ?
C36 C37 1.379(9) . ?
C37 F42 1.347(8) . ?

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
N19 C1 N2 116.8(5) . . ?
N19 C1 B29 124.3(5) . . ?
N2 C1 B29 118.4(5) . . ?
C1 N2 C12 124.7(5) . . ?
C1 N2 C3 122.6(5) . . ?
C12 N2 C3 112.6(4) . . ?
C4 C3 C8 122.9(5) . . ?
C4 C3 N2 117.4(5) . . ?
C8 C3 N2 119.3(5) . . ?
C5 C4 C3 117.6(6) . . ?
C5 C4 C9 119.8(6) . . ?
C3 C4 C9 122.5(5) . . ?
C4 C5 C6 121.6(6) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C7 C6 C5 118.7(6) . . ?
C7 C6 C10 121.1(7) . . ?
C5 C6 C10 120.1(7) . . ?
C6 C7 C8 122.3(6) . . ?
C6 C7 H7 118.8 . . ?
C8 C7 H7 118.8 . . ?
C7 C8 C3 116.1(6) . . ?
C7 C8 C11 119.0(6) . . ?
C3 C8 C11 124.7(5) . . ?
C4 C9 H9A 109.5 . . ?
C4 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C4 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C6 C10 H10A 109.5 . . ?
C6 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C6 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
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 . . ?
O13 C12 N2 119.0(5) . . ?
O13 C12 C14 124.7(5) . . ?
N2 C12 C14 116.2(5) . . ?
C17 C14 C12 111.1(5) . . ?
C17 C14 C16 110.8(5) . . ?
C12 C14 C16 111.0(5) . . ?
C17 C14 C15 106.0(5) . . ?
C12 C14 C15 106.2(5) . . ?
C16 C14 C15 111.6(5) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O18 C17 N19 118.5(5) . . ?
O18 C17 C14 124.1(6) . . ?
N19 C17 C14 117.1(5) . . ?
C1 N19 C17 123.9(5) . . ?
C1 N19 C20 123.6(5) . . ?
C17 N19 C20 112.2(4) . . ?
C21 C20 C25 123.0(6) . . ?
C21 C20 N19 119.6(6) . . ?
C25 C20 N19 117.0(5) . . ?
C20 C21 C22 116.5(6) . . ?
C20 C21 C26 123.0(6) . . ?
C22 C21 C26 120.5(6) . . ?
C23 C22 C21 122.4(6) . . ?
C23 C22 H22 118.8 . . ?
C21 C22 H22 118.8 . . ?
C22 C23 C24 118.3(6) . . ?
C22 C23 C27 121.1(7) . . ?
C24 C23 C27 120.6(7) . . ?
C25 C24 C23 121.9(7) . . ?
C25 C24 H24 119.0 . . ?
C23 C24 H24 119.0 . . ?
C24 C25 C20 117.2(6) . . ?
C24 C25 C28 120.3(6) . . ?
C20 C25 C28 122.4(6) . . ?
C21 C26 H26A 109.5 . . ?
C21 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C21 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C23 C27 H27A 109.5 . . ?
C23 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C23 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C25 C28 H28A 109.5 . . ?
C25 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C25 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C32 B29 C1 118.1(5) . . ?
C32 B29 Br31 102.8(4) . . ?
C1 B29 Br31 119.7(4) . . ?
C32 B29 Br30 116.6(5) . . ?
C1 B29 Br30 94.9(4) . . ?
Br31 B29 Br30 104.6(3) . . ?
C37 C32 C33 113.5(6) . . ?
C37 C32 B29 127.7(6) . . ?
C33 C32 B29 118.7(5) . . ?
F38 C33 C34 116.6(6) . . ?
F38 C33 C32 118.4(5) . . ?
C34 C33 C32 125.0(6) . . ?
F39 C34 C35 120.9(6) . . ?
F39 C34 C33 120.4(6) . . ?
C35 C34 C33 118.7(6) . . ?
F40 C35 C36 120.5(7) . . ?
F40 C35 C34 120.3(7) . . ?
C36 C35 C34 119.1(6) . . ?
C35 C36 F41 119.5(6) . . ?
C35 C36 C37 121.3(6) . . ?
F41 C36 C37 119.2(7) . . ?
F42 C37 C36 115.8(6) . . ?
F42 C37 C32 121.9(6) . . ?
C36 C37 C32 122.3(7) . . ?

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
N19 C1 N2 C12 -5.7(8) . . . . ?
B29 C1 N2 C12 166.0(5) . . . . ?
N19 C1 N2 C3 168.8(5) . . . . ?
B29 C1 N2 C3 -19.5(8) . . . . ?
C1 N2 C3 C4 -85.4(7) . . . . ?
C12 N2 C3 C4 89.8(6) . . . . ?
C1 N2 C3 C8 102.4(7) . . . . ?
C12 N2 C3 C8 -82.4(7) . . . . ?
C8 C3 C4 C5 -8.7(9) . . . . ?
N2 C3 C4 C5 179.4(5) . . . . ?
C8 C3 C4 C9 168.3(6) . . . . ?
N2 C3 C4 C9 -3.6(8) . . . . ?
C3 C4 C5 C6 2.0(9) . . . . ?
C9 C4 C5 C6 -175.1(6) . . . . ?
C4 C5 C6 C7 3.3(9) . . . . ?
C4 C5 C6 C10 179.6(6) . . . . ?
C5 C6 C7 C8 -2.3(9) . . . . ?
C10 C6 C7 C8 -178.5(6) . . . . ?
C6 C7 C8 C3 -3.9(9) . . . . ?
C6 C7 C8 C11 170.9(6) . . . . ?
C4 C3 C8 C7 9.5(9) . . . . ?
N2 C3 C8 C7 -178.7(5) . . . . ?
C4 C3 C8 C11 -164.9(6) . . . . ?
N2 C3 C8 C11 6.8(9) . . . . ?
C1 N2 C12 O13 167.6(6) . . . . ?
C3 N2 C12 O13 -7.5(8) . . . . ?
C1 N2 C12 C14 -16.2(8) . . . . ?
C3 N2 C12 C14 168.7(5) . . . . ?
O13 C12 C14 C17 -149.7(6) . . . . ?
N2 C12 C14 C17 34.4(7) . . . . ?
O13 C12 C14 C16 -25.9(9) . . . . ?
N2 C12 C14 C16 158.1(5) . . . . ?
O13 C12 C14 C15 95.5(7) . . . . ?
N2 C12 C14 C15 -80.4(6) . . . . ?
C12 C14 C17 O18 152.4(6) . . . . ?
C16 C14 C17 O18 28.5(8) . . . . ?
C15 C14 C17 O18 -92.7(7) . . . . ?
C12 C14 C17 N19 -33.6(7) . . . . ?
C16 C14 C17 N19 -157.4(5) . . . . ?
C15 C14 C17 N19 81.4(6) . . . . ?
N2 C1 N19 C17 6.9(8) . . . . ?
B29 C1 N19 C17 -164.3(5) . . . . ?
N2 C1 N19 C20 -166.6(5) . . . . ?
B29 C1 N19 C20 22.2(9) . . . . ?
O18 C17 N19 C1 -171.5(6) . . . . ?
C14 C17 N19 C1 14.1(8) . . . . ?
O18 C17 N19 C20 2.6(8) . . . . ?
C14 C17 N19 C20 -171.8(5) . . . . ?
C1 N19 C20 C21 -102.8(7) . . . . ?
C17 N19 C20 C21 83.1(7) . . . . ?
C1 N19 C20 C25 84.3(8) . . . . ?
C17 N19 C20 C25 -89.9(7) . . . . ?
C25 C20 C21 C22 -8.4(9) . . . . ?
N19 C20 C21 C22 179.1(5) . . . . ?
C25 C20 C21 C26 172.2(6) . . . . ?
N19 C20 C21 C26 -0.3(9) . . . . ?
C20 C21 C22 C23 2.3(10) . . . . ?
C26 C21 C22 C23 -178.4(6) . . . . ?
C21 C22 C23 C24 3.2(10) . . . . ?
C21 C22 C23 C27 -177.9(6) . . . . ?
C22 C23 C24 C25 -3.0(10) . . . . ?
C27 C23 C24 C25 178.2(6) . . . . ?
C23 C24 C25 C20 -2.7(9) . . . . ?
C23 C24 C25 C28 175.0(6) . . . . ?
C21 C20 C25 C24 8.7(10) . . . . ?
N19 C20 C25 C24 -178.6(5) . . . . ?
C21 C20 C25 C28 -169.0(5) . . . . ?
N19 C20 C25 C28 3.7(9) . . . . ?
N19 C1 B29 C32 -143.3(6) . . . . ?
N2 C1 B29 C32 45.7(8) . . . . ?
N19 C1 B29 Br31 -16.8(8) . . . . ?
N2 C1 B29 Br31 172.2(4) . . . . ?
N19 C1 B29 Br30 93.1(6) . . . . ?
N2 C1 B29 Br30 -78.0(5) . . . . ?
C1 B29 C32 C37 -116.0(7) . . . . ?
Br31 B29 C32 C37 109.8(6) . . . . ?
Br30 B29 C32 C37 -4.0(8) . . . . ?
C1 B29 C32 C33 68.0(7) . . . . ?
Br31 B29 C32 C33 -66.2(6) . . . . ?
Br30 B29 C32 C33 -180.0(4) . . . . ?
C37 C32 C33 F38 -178.5(5) . . . . ?
B29 C32 C33 F38 -1.9(8) . . . . ?
C37 C32 C33 C34 3.1(9) . . . . ?
B29 C32 C33 C34 179.6(5) . . . . ?
F38 C33 C34 F39 -0.7(8) . . . . ?
C32 C33 C34 F39 177.8(6) . . . . ?
F38 C33 C34 C35 -179.2(5) . . . . ?
C32 C33 C34 C35 -0.7(10) . . . . ?
F39 C34 C35 F40 -2.1(9) . . . . ?
C33 C34 C35 F40 176.3(5) . . . . ?
F39 C34 C35 C36 179.5(6) . . . . ?
C33 C34 C35 C36 -2.0(10) . . . . ?
F40 C35 C36 F41 2.2(10) . . . . ?
C34 C35 C36 F41 -179.4(5) . . . . ?
F40 C35 C36 C37 -176.2(5) . . . . ?
C34 C35 C36 C37 2.2(10) . . . . ?
C35 C36 C37 F42 179.8(6) . . . . ?
F41 C36 C37 F42 1.4(9) . . . . ?
C35 C36 C37 C32 0.5(10) . . . . ?
F41 C36 C37 C32 -178.0(5) . . . . ?
C33 C32 C37 F42 177.8(5) . . . . ?
B29 C32 C37 F42 1.6(10) . . . . ?
C33 C32 C37 C36 -2.9(9) . . . . ?
B29 C32 C37 C36 -179.1(6) . . . . ?

_refine_diff_density_max         0.601
_refine_diff_density_min         -0.853
_refine_diff_density_rms         0.086

####################################################################### 
# 
# 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_test_a
_database_code_depnum_ccdc_archive 'CCDC 1839163'
_audit_update_record             
;
2018-04-24 deposited with the CCDC.
2018-07-04 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C84 H104 B2 Br2 F10 Li2 N4 O10'
_chemical_formula_sum            'C84 H104 B2 Br2 F10 Li2 N4 O10'
_chemical_formula_weight         1715.03

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'
Li Li -0.0003 0.0001 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   10.2637(10)
_cell_length_b                   24.161(3)
_cell_length_c                   16.6779(17)
_cell_angle_alpha                90
_cell_angle_beta                 97.972(4)
_cell_angle_gamma                90
_cell_volume                     4095.8(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9936
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      24.85


_exptl_special_details           
;
The crystal was immersed in a film of perfluoropolyether oil, mounted on a 
polyimide microloop (MicroMounts of MiTeGen) and transferred to stream of cold 
nitrogen (Bruker Kryoflex2).
;
_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_F_000             1784
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    1.073
_shelx_estimated_absorpt_T_min   0.806
_shelx_estimated_absorpt_T_max   0.938
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6819
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   'SadAbs 2016/2 (Bruker AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'multi-layer mirror'
_diffrn_source                   'microfocus sealed tube (Incoatec ImS)'
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector                 'CMOS area detector (Photon 100)'
_diffrn_detector_area_resol_mean 10.24
_diffrn_reflns_number            51264
_diffrn_reflns_av_unetI/netI     0.0629
_diffrn_reflns_av_R_equivalents  0.0897
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.174
_diffrn_reflns_theta_max         26.020
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             8075
_reflns_number_gt                5654
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 ver. 2014.9 (Bruker AXS)'
_computing_cell_refinement       'Saint+ ver. V8.37A (Bruker AXS)'
_computing_data_reduction        'Saint+ ver. V8.37A (Bruker AXS)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2016/6 (Sheldrick, 2016)'
_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     
'w=1/[σ²(Fo²)+(0.0425P)²+3.7916P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8075
_refine_ls_number_parameters     542
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0853
_refine_ls_R_factor_gt           0.0460
_refine_ls_wR_factor_ref         0.1031
_refine_ls_wR_factor_gt          0.0908
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
Br01 Br 0.11458(3) 0.65355(2) 0.74539(2) 0.02584(10) Uani 1 1 d . . . . .
B1 B 0.2914(3) 0.61824(14) 0.75531(19) 0.0166(7) Uani 1 1 d . . . . .
C1 C 0.4534(3) 0.50752(12) 0.64893(15) 0.0143(6) Uani 1 1 d . . . . .
F002 F 0.52760(15) 0.68520(7) 0.80010(9) 0.0220(4) Uani 1 1 d . . . . .
C2 C 0.2920(2) 0.55484(12) 0.54974(16) 0.0156(6) Uani 1 1 d . . . . .
O2 O 0.54718(18) 0.47477(8) 0.65634(10) 0.0177(4) Uani 1 1 d . . . . .
F003 F 0.65041(17) 0.70182(7) 0.95010(10) 0.0324(4) Uani 1 1 d . . . . .
F004 F 0.20916(17) 0.57526(7) 0.90540(10) 0.0299(4) Uani 1 1 d . . . . .
F005 F 0.32781(19) 0.59663(8) 1.05545(10) 0.0377(5) Uani 1 1 d . . . . .
F007 F 0.55388(19) 0.65702(8) 1.07922(10) 0.0403(5) Uani 1 1 d . . . . .
O008 O 0.26516(17) 0.56177(8) 0.47537(10) 0.0175(4) Uani 1 1 d . . . . .
O009 O 0.17854(17) 0.57300(8) 0.29060(11) 0.0198(5) Uani 1 1 d . . . . .
O00A O 0.40127(19) 0.65007(8) 0.36950(12) 0.0260(5) Uani 1 1 d . . . . .
N00B N 0.4514(2) 0.55277(9) 0.69652(12) 0.0129(5) Uani 1 1 d . . . . .
N00C N 0.2844(2) 0.59629(9) 0.60330(12) 0.0133(5) Uani 1 1 d . . . . .
C00D C 0.5511(3) 0.55475(11) 0.76795(15) 0.0143(6) Uani 1 1 d . . . . .
C00F C 0.6680(3) 0.58348(12) 0.76642(16) 0.0164(6) Uani 1 1 d . . . . .
C00G C 0.3643(3) 0.62736(12) 0.84544(16) 0.0185(6) Uani 1 1 d . . . . .
C00H C 0.5276(3) 0.52438(12) 0.83640(16) 0.0162(6) Uani 1 1 d . . . . .
C00J C 0.3053(3) 0.69482(12) 0.57006(15) 0.0170(6) Uani 1 1 d . . . . .
C00K C 0.4762(3) 0.66038(12) 0.86144(16) 0.0194(6) Uani 1 1 d . . . . .
C00L C 0.3320(3) 0.49921(12) 0.58681(16) 0.0160(6) Uani 1 1 d . . . . .
C00M C 0.2265(3) 0.64827(12) 0.57325(15) 0.0163(6) Uani 1 1 d . . . . .
C00N C 0.0911(3) 0.65056(13) 0.54741(16) 0.0208(6) Uani 1 1 d . . . . .
C00O C 0.7569(3) 0.58621(12) 0.83775(17) 0.0197(6) Uani 1 1 d . . . . .
H00O H 0.836433 0.606345 0.837825 0.024 Uiso 1 1 calc R U . . .
C00P C 0.3399(2) 0.59074(11) 0.68824(15) 0.0136(6) Uani 1 1 d . . . . .
C00Q C 0.4106(3) 0.48678(12) 0.83429(16) 0.0214(7) Uani 1 1 d . . . . .
H00A H 0.331382 0.506280 0.809574 0.032 Uiso 1 1 calc R U . . .
H00B H 0.400172 0.475790 0.889599 0.032 Uiso 1 1 calc R U . . .
H00C H 0.424005 0.453749 0.802320 0.032 Uiso 1 1 calc R U . . .
C00R C 0.4528(3) 0.69154(12) 0.59030(17) 0.0209(6) Uani 1 1 d . . . . .
H00D H 0.486349 0.662270 0.557993 0.031 Uiso 1 1 calc R U . . .
H00E H 0.476276 0.683156 0.647987 0.031 Uiso 1 1 calc R U . . .
H00F H 0.491743 0.727066 0.578088 0.031 Uiso 1 1 calc R U . . .
C00S C 0.3562(3) 0.45699(12) 0.52192(16) 0.0195(6) Uani 1 1 d . . . . .
H00G H 0.277169 0.453808 0.481859 0.029 Uiso 1 1 calc R U . . .
H00H H 0.376796 0.420882 0.547332 0.029 Uiso 1 1 calc R U . . .
H00I H 0.430258 0.469278 0.495058 0.029 Uiso 1 1 calc R U . . .
C00T C 0.4922(3) 0.64807(13) 1.00354(17) 0.0264(7) Uani 1 1 d . . . . .
C00U C 0.7037(3) 0.61029(13) 0.69075(17) 0.0225(7) Uani 1 1 d . . . . .
H00J H 0.648900 0.594810 0.643255 0.034 Uiso 1 1 calc R U . . .
H00K H 0.796615 0.603192 0.686769 0.034 Uiso 1 1 calc R U . . .
H00L H 0.688881 0.650295 0.693066 0.034 Uiso 1 1 calc R U . . .
C00V C 0.2453(3) 0.74482(13) 0.54580(16) 0.0228(7) Uani 1 1 d . . . . .
H00V H 0.298067 0.777098 0.545500 0.027 Uiso 1 1 calc R U . . .
C00W C 0.5411(3) 0.67071(12) 0.93861(18) 0.0240(7) Uani 1 1 d . . . . .
C00X C 0.3183(3) 0.60703(12) 0.91282(18) 0.0237(7) Uani 1 1 d . . . . .
C00Y C 0.7326(3) 0.56036(12) 0.90850(17) 0.0201(6) Uani 1 1 d . . . . .
C00Z C 0.2193(3) 0.47789(13) 0.63123(17) 0.0205(7) Uani 1 1 d . . . . .
H00M H 0.139852 0.472521 0.592063 0.031 Uiso 1 1 calc R U . . .
H00N H 0.201501 0.505040 0.672001 0.031 Uiso 1 1 calc R U . . .
H00P H 0.245051 0.442604 0.657772 0.031 Uiso 1 1 calc R U . . .
C010 C 0.0360(3) 0.70145(14) 0.52251(17) 0.0263(7) Uani 1 1 d . . . . .
H010 H -0.056099 0.703464 0.505271 0.032 Uiso 1 1 calc R U . . .
C011 C 0.6192(3) 0.52894(12) 0.90591(16) 0.0193(6) Uani 1 1 d . . . . .
H011 H 0.603368 0.509771 0.953346 0.023 Uiso 1 1 calc R U . . .
C012 C 0.3795(3) 0.61707(13) 0.99142(17) 0.0271(7) Uani 1 1 d . . . . .
C013 C 0.1101(3) 0.74905(13) 0.52193(17) 0.0251(7) Uani 1 1 d . . . . .
C014 C 0.2035(3) 0.56586(14) 0.20836(16) 0.0270(7) Uani 1 1 d . . . . .
H01A H 0.265806 0.534971 0.204711 0.032 Uiso 1 1 calc R U . . .
H01B H 0.241503 0.600034 0.188416 0.032 Uiso 1 1 calc R U . . .
C015 C 0.8286(3) 0.56525(14) 0.98544(18) 0.0309(8) Uani 1 1 d . . . . .
H01C H 0.915932 0.574624 0.971980 0.046 Uiso 1 1 calc R U . . .
H01D H 0.833115 0.529918 1.014565 0.046 Uiso 1 1 calc R U . . .
H01E H 0.799168 0.594361 1.019683 0.046 Uiso 1 1 calc R U . . .
C016 C 0.0733(3) 0.55335(15) 0.15976(18) 0.0322(8) Uani 1 1 d . . . . .
H01F H 0.083524 0.529564 0.112709 0.039 Uiso 1 1 calc R U . . .
H01G H 0.026770 0.587743 0.140366 0.039 Uiso 1 1 calc R U . . .
C017 C 0.0052(3) 0.60015(14) 0.54768(19) 0.0291(8) Uani 1 1 d . . . . .
H01H H -0.087413 0.611190 0.536968 0.044 Uiso 1 1 calc R U . . .
H01I H 0.022288 0.582015 0.600654 0.044 Uiso 1 1 calc R U . . .
H01J H 0.024904 0.574389 0.505574 0.044 Uiso 1 1 calc R U . . .
C01A C 0.5072(3) 0.66415(14) 0.3256(2) 0.0321(8) Uani 1 1 d . . . . .
H01K H 0.558933 0.630856 0.315769 0.038 Uiso 1 1 calc R U . . .
H01L H 0.566465 0.691587 0.355887 0.038 Uiso 1 1 calc R U . . .
C01B C 0.3116(3) 0.69523(14) 0.3551(2) 0.0361(8) Uani 1 1 d . . . . .
H01M H 0.341370 0.726921 0.390608 0.043 Uiso 1 1 calc R U . . .
H01N H 0.222590 0.684095 0.365516 0.043 Uiso 1 1 calc R U . . .
C01C C 0.4419(4) 0.68831(14) 0.24664(19) 0.0372(9) Uani 1 1 d . . . . .
H01O H 0.427777 0.659548 0.204029 0.045 Uiso 1 1 calc R U . . .
H01P H 0.495741 0.718483 0.228089 0.045 Uiso 1 1 calc R U . . .
C01D C 0.0492(3) 0.80432(15) 0.4952(2) 0.0397(9) Uani 1 1 d . . . . .
H01Q H 0.074127 0.814314 0.442424 0.060 Uiso 1 1 calc R U . . .
H01R H 0.080986 0.832756 0.535076 0.060 Uiso 1 1 calc R U . . .
H01S H -0.046770 0.801657 0.490775 0.060 Uiso 1 1 calc R U . . .
C01E C 0.0009(3) 0.52320(19) 0.2199(2) 0.0479(11) Uani 1 1 d . . . . .
H01T H -0.093231 0.533726 0.212586 0.058 Uiso 1 1 calc R U . . .
H01U H 0.007647 0.482621 0.213329 0.058 Uiso 1 1 calc R U . . .
C01F C 0.3103(4) 0.71053(15) 0.2669(2) 0.0430(9) Uani 1 1 d . . . . .
H01V H 0.304399 0.751133 0.259278 0.052 Uiso 1 1 calc R U . . .
H01W H 0.235357 0.692827 0.232519 0.052 Uiso 1 1 calc R U . . .
C01G C 0.0673(3) 0.54089(19) 0.3009(2) 0.0526(12) Uani 1 1 d . . . . .
H01X H 0.005935 0.562930 0.328913 0.063 Uiso 1 1 calc R U . . .
H01Y H 0.094631 0.507985 0.334497 0.063 Uiso 1 1 calc R U . . .
Li1J Li 0.3298(4) 0.5754(2) 0.3765(3) 0.0190(10) Uani 1 1 d . . . . .
O1_1 O 0.8236(11) 0.6475(4) 1.2502(5) 0.066(2) Uani 0.7 1 d . . P A 1
C1_1 C 0.8650(9) 0.6792(3) 1.1866(4) 0.061(2) Uani 0.7 1 d . . P A 1
H1A_1 H 0.821626 0.665569 1.133534 0.074 Uiso 0.7 1 calc R U P A 1
H1B_1 H 0.961442 0.675975 1.187800 0.074 Uiso 0.7 1 calc R U P A 1
C2_1 C 0.8268(6) 0.7395(2) 1.1990(4) 0.0538(17) Uani 0.7 1 d . . P A 1
H2A_1 H 0.886562 0.765349 1.175831 0.065 Uiso 0.7 1 calc R U P A 1
H2B_1 H 0.735101 0.746970 1.174423 0.065 Uiso 0.7 1 calc R U P A 1
C3_1 C 0.8419(8) 0.7442(3) 1.2892(4) 0.065(2) Uani 0.7 1 d . . P A 1
H3A_1 H 0.760183 0.758169 1.307465 0.078 Uiso 0.7 1 calc R U P A 1
H3B_1 H 0.915731 0.769014 1.309791 0.078 Uiso 0.7 1 calc R U P A 1
C4_1 C 0.8707(18) 0.6834(8) 1.3177(10) 0.089(6) Uani 0.7 1 d . . P A 1
H4A_1 H 0.966359 0.678100 1.333997 0.107 Uiso 0.7 1 calc R U P A 1
H4B_1 H 0.824891 0.674931 1.364697 0.107 Uiso 0.7 1 calc R U P A 1
O1_2 O 0.803(2) 0.6550(9) 1.2647(14) 0.046(5) Uiso 0.3 1 d . . P B 2
C1_2 C 0.8061(16) 0.6843(8) 1.1867(11) 0.045(5) Uiso 0.3 1 d . . P B 2
H1A_2 H 0.828546 0.658705 1.144263 0.055 Uiso 0.3 1 calc R U P B 2
H1B_2 H 0.720823 0.702324 1.167706 0.055 Uiso 0.3 1 calc R U P B 2
C2_2 C 0.9082(16) 0.7244(7) 1.2080(9) 0.056(4) Uiso 0.3 1 d . . P B 2
H2A_2 H 0.885783 0.760282 1.180959 0.068 Uiso 0.3 1 calc R U P B 2
H2B_2 H 0.993445 0.711253 1.193797 0.068 Uiso 0.3 1 calc R U P B 2
C3_2 C 0.864(3) 0.6781(13) 1.329(2) 0.035(6) Uiso 0.3 1 d . . P B 2
H3A_2 H 0.937565 0.654478 1.353305 0.042 Uiso 0.3 1 calc R U P B 2
H3B_2 H 0.803388 0.684507 1.368898 0.042 Uiso 0.3 1 calc R U P B 2
C4_2 C 0.9120(14) 0.7292(6) 1.3021(8) 0.038(4) Uiso 0.3 1 d . . P B 2
H4A_2 H 1.003096 0.735821 1.328541 0.045 Uiso 0.3 1 calc R U P B 2
H4B_2 H 0.855879 0.760206 1.315576 0.045 Uiso 0.3 1 calc R U P B 2


_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
Br01 B1 1.992(3) . ?
B1 C00P 1.447(4) . ?
B1 C00G 1.599(4) . ?
C1 O2 1.239(3) . ?
C1 N00B 1.353(3) . ?
C1 C00L 1.520(4) . ?
F002 C00K 1.354(3) . ?
C2 O008 1.244(3) . ?
C2 N00C 1.351(3) . ?
C2 C00L 1.512(4) . ?
O2 Li1J 1.885(5) 3_666 ?
F003 C00W 1.342(3) . ?
F004 C00X 1.349(3) . ?
F005 C012 1.350(3) . ?
F007 C00T 1.349(3) . ?
O008 Li1J 1.890(5) . ?
O009 C01G 1.410(4) . ?
O009 C014 1.440(3) . ?
O009 Li1J 1.961(5) . ?
O00A C01B 1.426(4) . ?
O00A C01A 1.434(3) . ?
O00A Li1J 1.957(5) . ?
N00B C00P 1.458(3) . ?
N00B C00D 1.460(3) . ?
N00C C00M 1.449(4) . ?
N00C C00P 1.458(3) . ?
C00D C00F 1.389(4) . ?
C00D C00H 1.406(4) . ?
C00F C00O 1.397(4) . ?
C00F C00U 1.508(4) . ?
C00G C00X 1.369(4) . ?
C00G C00K 1.393(4) . ?
C00H C011 1.392(4) . ?
C00H C00Q 1.502(4) . ?
C00J C00V 1.391(4) . ?
C00J C00M 1.391(4) . ?
C00J C00R 1.506(4) . ?
C00K C00W 1.387(4) . ?
C00L C00S 1.532(4) . ?
C00L C00Z 1.546(3) . ?
C00M C00N 1.397(4) . ?
C00N C010 1.393(4) . ?
C00N C017 1.504(4) . ?
C00O C00Y 1.388(4) . ?
C00O H00O 0.9500 . ?
C00Q H00A 0.9800 . ?
C00Q H00B 0.9800 . ?
C00Q H00C 0.9800 . ?
C00R H00D 0.9800 . ?
C00R H00E 0.9800 . ?
C00R H00F 0.9800 . ?
C00S H00G 0.9800 . ?
C00S H00H 0.9800 . ?
C00S H00I 0.9800 . ?
C00T C012 1.369(4) . ?
C00T C00W 1.369(4) . ?
C00U H00J 0.9800 . ?
C00U H00K 0.9800 . ?
C00U H00L 0.9800 . ?
C00V C013 1.393(4) . ?
C00V H00V 0.9500 . ?
C00X C012 1.394(4) . ?
C00Y C011 1.385(4) . ?
C00Y C015 1.510(4) . ?
C00Z H00M 0.9800 . ?
C00Z H00N 0.9800 . ?
C00Z H00P 0.9800 . ?
C010 C013 1.380(4) . ?
C010 H010 0.9500 . ?
C011 H011 0.9500 . ?
C013 C01D 1.515(4) . ?
C014 C016 1.495(4) . ?
C014 H01A 0.9900 . ?
C014 H01B 0.9900 . ?
C015 H01C 0.9800 . ?
C015 H01D 0.9800 . ?
C015 H01E 0.9800 . ?
C016 C01E 1.515(5) . ?
C016 H01F 0.9900 . ?
C016 H01G 0.9900 . ?
C017 H01H 0.9800 . ?
C017 H01I 0.9800 . ?
C017 H01J 0.9800 . ?
C01A C01C 1.509(5) . ?
C01A H01K 0.9900 . ?
C01A H01L 0.9900 . ?
C01B C01F 1.516(5) . ?
C01B H01M 0.9900 . ?
C01B H01N 0.9900 . ?
C01C C01F 1.534(5) . ?
C01C H01O 0.9900 . ?
C01C H01P 0.9900 . ?
C01D H01Q 0.9800 . ?
C01D H01R 0.9800 . ?
C01D H01S 0.9800 . ?
C01E C01G 1.489(5) . ?
C01E H01T 0.9900 . ?
C01E H01U 0.9900 . ?
C01F H01V 0.9900 . ?
C01F H01W 0.9900 . ?
C01G H01X 0.9900 . ?
C01G H01Y 0.9900 . ?
O1_1 C1_1 1.420(13) . ?
O1_1 C4_1 1.451(19) . ?
C1_1 C2_1 1.532(9) . ?
C1_1 H1A_1 0.9900 . ?
C1_1 H1B_1 0.9900 . ?
C2_1 C3_1 1.495(9) . ?
C2_1 H2A_1 0.9900 . ?
C2_1 H2B_1 0.9900 . ?
C3_1 C4_1 1.558(18) . ?
C3_1 H3A_1 0.9900 . ?
C3_1 H3B_1 0.9900 . ?
C4_1 H4A_1 0.9900 . ?
C4_1 H4B_1 0.9900 . ?
O1_2 C3_2 1.29(4) . ?
O1_2 C1_2 1.49(3) . ?
C1_2 C2_2 1.44(2) . ?
C1_2 H1A_2 0.9900 . ?
C1_2 H1B_2 0.9900 . ?
C2_2 C4_2 1.57(2) . ?
C2_2 H2A_2 0.9900 . ?
C2_2 H2B_2 0.9900 . ?
C3_2 C4_2 1.42(4) . ?
C3_2 H3A_2 0.9900 . ?
C3_2 H3B_2 0.9900 . ?
C4_2 H4A_2 0.9900 . ?
C4_2 H4B_2 0.9900 . ?

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
C00P B1 C00G 128.6(3) . . ?
C00P B1 Br01 122.7(2) . . ?
C00G B1 Br01 108.74(19) . . ?
O2 C1 N00B 122.2(2) . . ?
O2 C1 C00L 122.4(2) . . ?
N00B C1 C00L 115.4(2) . . ?
O008 C2 N00C 122.3(3) . . ?
O008 C2 C00L 122.5(2) . . ?
N00C C2 C00L 115.2(2) . . ?
C1 O2 Li1J 157.5(2) . 3_666 ?
C2 O008 Li1J 146.9(2) . . ?
C01G O009 C014 107.7(2) . . ?
C01G O009 Li1J 119.9(2) . . ?
C014 O009 Li1J 118.1(2) . . ?
C01B O00A C01A 104.5(2) . . ?
C01B O00A Li1J 118.5(2) . . ?
C01A O00A Li1J 124.5(2) . . ?
C1 N00B C00P 121.9(2) . . ?
C1 N00B C00D 116.1(2) . . ?
C00P N00B C00D 120.6(2) . . ?
C2 N00C C00M 118.2(2) . . ?
C2 N00C C00P 121.6(2) . . ?
C00M N00C C00P 120.1(2) . . ?
C00F C00D C00H 121.4(2) . . ?
C00F C00D N00B 120.7(2) . . ?
C00H C00D N00B 117.8(2) . . ?
C00D C00F C00O 118.2(2) . . ?
C00D C00F C00U 122.7(2) . . ?
C00O C00F C00U 119.1(2) . . ?
C00X C00G C00K 114.7(3) . . ?
C00X C00G B1 123.5(3) . . ?
C00K C00G B1 121.7(2) . . ?
C011 C00H C00D 117.6(3) . . ?
C011 C00H C00Q 120.8(2) . . ?
C00D C00H C00Q 121.5(2) . . ?
C00V C00J C00M 118.5(3) . . ?
C00V C00J C00R 120.1(3) . . ?
C00M C00J C00R 121.4(3) . . ?
F002 C00K C00W 115.7(3) . . ?
F002 C00K C00G 120.4(2) . . ?
C00W C00K C00G 123.9(3) . . ?
C2 C00L C1 108.1(2) . . ?
C2 C00L C00S 111.4(2) . . ?
C1 C00L C00S 111.8(2) . . ?
C2 C00L C00Z 108.3(2) . . ?
C1 C00L C00Z 108.4(2) . . ?
C00S C00L C00Z 108.8(2) . . ?
C00J C00M C00N 121.0(3) . . ?
C00J C00M N00C 120.0(2) . . ?
C00N C00M N00C 119.0(3) . . ?
C010 C00N C00M 118.2(3) . . ?
C010 C00N C017 120.1(3) . . ?
C00M C00N C017 121.7(3) . . ?
C00Y C00O C00F 122.0(3) . . ?
C00Y C00O H00O 119.0 . . ?
C00F C00O H00O 119.0 . . ?
B1 C00P N00C 125.4(2) . . ?
B1 C00P N00B 124.4(2) . . ?
N00C C00P N00B 110.2(2) . . ?
C00H C00Q H00A 109.5 . . ?
C00H C00Q H00B 109.5 . . ?
H00A C00Q H00B 109.5 . . ?
C00H C00Q H00C 109.5 . . ?
H00A C00Q H00C 109.5 . . ?
H00B C00Q H00C 109.5 . . ?
C00J C00R H00D 109.5 . . ?
C00J C00R H00E 109.5 . . ?
H00D C00R H00E 109.5 . . ?
C00J C00R H00F 109.5 . . ?
H00D C00R H00F 109.5 . . ?
H00E C00R H00F 109.5 . . ?
C00L C00S H00G 109.5 . . ?
C00L C00S H00H 109.5 . . ?
H00G C00S H00H 109.5 . . ?
C00L C00S H00I 109.5 . . ?
H00G C00S H00I 109.5 . . ?
H00H C00S H00I 109.5 . . ?
F007 C00T C012 120.2(3) . . ?
F007 C00T C00W 120.0(3) . . ?
C012 C00T C00W 119.8(3) . . ?
C00F C00U H00J 109.5 . . ?
C00F C00U H00K 109.5 . . ?
H00J C00U H00K 109.5 . . ?
C00F C00U H00L 109.5 . . ?
H00J C00U H00L 109.5 . . ?
H00K C00U H00L 109.5 . . ?
C00J C00V C013 122.0(3) . . ?
C00J C00V H00V 119.0 . . ?
C013 C00V H00V 119.0 . . ?
F003 C00W C00T 120.1(3) . . ?
F003 C00W C00K 121.2(3) . . ?
C00T C00W C00K 118.7(3) . . ?
F004 C00X C00G 120.4(3) . . ?
F004 C00X C012 116.4(3) . . ?
C00G C00X C012 123.2(3) . . ?
C011 C00Y C00O 118.0(3) . . ?
C011 C00Y C015 121.1(3) . . ?
C00O C00Y C015 120.9(3) . . ?
C00L C00Z H00M 109.5 . . ?
C00L C00Z H00N 109.5 . . ?
H00M C00Z H00N 109.5 . . ?
C00L C00Z H00P 109.5 . . ?
H00M C00Z H00P 109.5 . . ?
H00N C00Z H00P 109.5 . . ?
C013 C010 C00N 122.4(3) . . ?
C013 C010 H010 118.8 . . ?
C00N C010 H010 118.8 . . ?
C00Y C011 C00H 122.5(3) . . ?
C00Y C011 H011 118.8 . . ?
C00H C011 H011 118.8 . . ?
F005 C012 C00T 120.0(3) . . ?
F005 C012 C00X 120.3(3) . . ?
C00T C012 C00X 119.7(3) . . ?
C010 C013 C00V 117.7(3) . . ?
C010 C013 C01D 122.1(3) . . ?
C00V C013 C01D 120.2(3) . . ?
O009 C014 C016 106.0(2) . . ?
O009 C014 H01A 110.5 . . ?
C016 C014 H01A 110.5 . . ?
O009 C014 H01B 110.5 . . ?
C016 C014 H01B 110.5 . . ?
H01A C014 H01B 108.7 . . ?
C00Y C015 H01C 109.5 . . ?
C00Y C015 H01D 109.5 . . ?
H01C C015 H01D 109.5 . . ?
C00Y C015 H01E 109.5 . . ?
H01C C015 H01E 109.5 . . ?
H01D C015 H01E 109.5 . . ?
C014 C016 C01E 102.8(2) . . ?
C014 C016 H01F 111.2 . . ?
C01E C016 H01F 111.2 . . ?
C014 C016 H01G 111.2 . . ?
C01E C016 H01G 111.2 . . ?
H01F C016 H01G 109.1 . . ?
C00N C017 H01H 109.5 . . ?
C00N C017 H01I 109.5 . . ?
H01H C017 H01I 109.5 . . ?
C00N C017 H01J 109.5 . . ?
H01H C017 H01J 109.5 . . ?
H01I C017 H01J 109.5 . . ?
O00A C01A C01C 105.1(3) . . ?
O00A C01A H01K 110.7 . . ?
C01C C01A H01K 110.7 . . ?
O00A C01A H01L 110.7 . . ?
C01C C01A H01L 110.7 . . ?
H01K C01A H01L 108.8 . . ?
O00A C01B C01F 105.6(2) . . ?
O00A C01B H01M 110.6 . . ?
C01F C01B H01M 110.6 . . ?
O00A C01B H01N 110.6 . . ?
C01F C01B H01N 110.6 . . ?
H01M C01B H01N 108.8 . . ?
C01A C01C C01F 104.0(3) . . ?
C01A C01C H01O 111.0 . . ?
C01F C01C H01O 111.0 . . ?
C01A C01C H01P 111.0 . . ?
C01F C01C H01P 111.0 . . ?
H01O C01C H01P 109.0 . . ?
C013 C01D H01Q 109.5 . . ?
C013 C01D H01R 109.5 . . ?
H01Q C01D H01R 109.5 . . ?
C013 C01D H01S 109.5 . . ?
H01Q C01D H01S 109.5 . . ?
H01R C01D H01S 109.5 . . ?
C01G C01E C016 104.9(3) . . ?
C01G C01E H01T 110.8 . . ?
C016 C01E H01T 110.8 . . ?
C01G C01E H01U 110.8 . . ?
C016 C01E H01U 110.8 . . ?
H01T C01E H01U 108.8 . . ?
C01B C01F C01C 103.8(3) . . ?
C01B C01F H01V 111.0 . . ?
C01C C01F H01V 111.0 . . ?
C01B C01F H01W 111.0 . . ?
C01C C01F H01W 111.0 . . ?
H01V C01F H01W 109.0 . . ?
O009 C01G C01E 108.9(3) . . ?
O009 C01G H01X 109.9 . . ?
C01E C01G H01X 109.9 . . ?
O009 C01G H01Y 109.9 . . ?
C01E C01G H01Y 109.9 . . ?
H01X C01G H01Y 108.3 . . ?
O2 Li1J O008 118.1(3) 3_666 . ?
O2 Li1J O00A 107.7(2) 3_666 . ?
O008 Li1J O00A 113.1(2) . . ?
O2 Li1J O009 105.3(2) 3_666 . ?
O008 Li1J O009 107.1(2) . . ?
O00A Li1J O009 104.4(2) . . ?
C1_1 O1_1 C4_1 98.9(9) . . ?
O1_1 C1_1 C2_1 107.7(6) . . ?
O1_1 C1_1 H1A_1 110.2 . . ?
C2_1 C1_1 H1A_1 110.2 . . ?
O1_1 C1_1 H1B_1 110.2 . . ?
C2_1 C1_1 H1B_1 110.2 . . ?
H1A_1 C1_1 H1B_1 108.5 . . ?
C3_1 C2_1 C1_1 102.4(6) . . ?
C3_1 C2_1 H2A_1 111.3 . . ?
C1_1 C2_1 H2A_1 111.3 . . ?
C3_1 C2_1 H2B_1 111.3 . . ?
C1_1 C2_1 H2B_1 111.3 . . ?
H2A_1 C2_1 H2B_1 109.2 . . ?
C2_1 C3_1 C4_1 103.0(7) . . ?
C2_1 C3_1 H3A_1 111.2 . . ?
C4_1 C3_1 H3A_1 111.2 . . ?
C2_1 C3_1 H3B_1 111.2 . . ?
C4_1 C3_1 H3B_1 111.2 . . ?
H3A_1 C3_1 H3B_1 109.1 . . ?
O1_1 C4_1 C3_1 107.4(11) . . ?
O1_1 C4_1 H4A_1 110.2 . . ?
C3_1 C4_1 H4A_1 110.2 . . ?
O1_1 C4_1 H4B_1 110.2 . . ?
C3_1 C4_1 H4B_1 110.2 . . ?
H4A_1 C4_1 H4B_1 108.5 . . ?
C3_2 O1_2 C1_2 117(2) . . ?
C2_2 C1_2 O1_2 102.1(15) . . ?
C2_2 C1_2 H1A_2 111.4 . . ?
O1_2 C1_2 H1A_2 111.4 . . ?
C2_2 C1_2 H1B_2 111.4 . . ?
O1_2 C1_2 H1B_2 111.4 . . ?
H1A_2 C1_2 H1B_2 109.2 . . ?
C1_2 C2_2 C4_2 102.4(13) . . ?
C1_2 C2_2 H2A_2 111.3 . . ?
C4_2 C2_2 H2A_2 111.3 . . ?
C1_2 C2_2 H2B_2 111.3 . . ?
C4_2 C2_2 H2B_2 111.3 . . ?
H2A_2 C2_2 H2B_2 109.2 . . ?
O1_2 C3_2 C4_2 106(3) . . ?
O1_2 C3_2 H3A_2 110.6 . . ?
C4_2 C3_2 H3A_2 110.6 . . ?
O1_2 C3_2 H3B_2 110.6 . . ?
C4_2 C3_2 H3B_2 110.6 . . ?
H3A_2 C3_2 H3B_2 108.7 . . ?
C3_2 C4_2 C2_2 106.5(18) . . ?
C3_2 C4_2 H4A_2 110.4 . . ?
C2_2 C4_2 H4A_2 110.4 . . ?
C3_2 C4_2 H4B_2 110.4 . . ?
C2_2 C4_2 H4B_2 110.4 . . ?
H4A_2 C4_2 H4B_2 108.6 . . ?

_refine_diff_density_max         0.595
_refine_diff_density_min         -0.465
_refine_diff_density_rms         0.069

####################################################################### 
# 
# 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_test_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1839160'
_audit_update_record             
;
2018-04-24 deposited with the CCDC.
2018-07-04 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H28 B Br F5 N2 O2'
_chemical_formula_sum            'C30 H28 B Br F5 N2 O2'
_chemical_formula_weight         634.26

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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.394(2)
_cell_length_b                   11.982(4)
_cell_length_c                   16.917(6)
_cell_angle_alpha                104.90(2)
_cell_angle_beta                 102.465(12)
_cell_angle_gamma                99.493(19)
_cell_volume                     1375.2(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9813
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      26.77


_exptl_special_details           
;
The crystal was immersed in a film of perfluoropolyether oil, mounted on a 
polyimide microloop (MicroMounts of MiTeGen) and transferred to stream of cold 
nitrogen (Oxford Cryostream 700).
;
_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.532
_exptl_crystal_F_000             646
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    1.561
_shelx_estimated_absorpt_T_min   0.745
_shelx_estimated_absorpt_T_max   0.745
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5755
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'SadAbs 2014/5 (Bruker AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'multi-layer mirror'
_diffrn_source                   'rotating-anode (Nonius FR-591)'
_diffrn_measurement_device_type  'Bruker X8-APEX II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector                 'CCD area detector (Apex2)'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            31455
_diffrn_reflns_av_unetI/netI     0.0418
_diffrn_reflns_av_R_equivalents  0.0605
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.294
_diffrn_reflns_theta_max         26.899
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5920
_reflns_number_gt                5000
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 ver. 2014.9 (Bruker AXS)'
_computing_cell_refinement       'Saint+ ver. V8.37A (Bruker AXS)'
_computing_data_reduction        'Saint+ ver. V8.37A (Bruker AXS)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_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     
'w=1/[σ²(Fo²)+(0.0480P)²+0.7114P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5920
_refine_ls_number_parameters     378
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0350
_refine_ls_wR_factor_ref         0.0922
_refine_ls_wR_factor_gt          0.0871
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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_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
C1_1 C 0.2098(3) 0.49740(19) 0.73759(13) 0.0128(4) Uani 1 1 d . . . . .
N2_1 N 0.1325(2) 0.37597(15) 0.71289(11) 0.0121(4) Uani 1 1 d . . . . .
C3_1 C 0.0400(3) 0.32053(19) 0.76179(13) 0.0137(4) Uani 1 1 d . . . . .
C4_1 C 0.0645(3) 0.39560(19) 0.85233(13) 0.0144(4) Uani 1 1 d . . . . .
C5_1 C 0.0494(3) 0.51954(19) 0.85252(13) 0.0131(4) Uani 1 1 d . . . . .
N6_1 N 0.1455(2) 0.56635(15) 0.80148(11) 0.0117(4) Uani 1 1 d . . . . .
O7_1 O -0.0455(2) 0.21816(13) 0.73340(10) 0.0185(3) Uani 1 1 d . . . . .
O8_1 O -0.0341(2) 0.57747(14) 0.89501(9) 0.0169(3) Uani 1 1 d . . . . .
C9_1 C 0.2666(3) 0.4027(2) 0.90671(14) 0.0179(5) Uani 1 1 d . . . . .
H9A_1 H 0.2792 0.3244 0.9071 0.027 Uiso 1 1 calc R U . . .
H9B_1 H 0.2850 0.4517 0.9638 0.027 Uiso 1 1 calc R U . . .
H9C_1 H 0.3605 0.4365 0.8828 0.027 Uiso 1 1 calc R U . . .
C10_1 C -0.0837(3) 0.3410(2) 0.89002(14) 0.0198(5) Uani 1 1 d . . . . .
H10A_1 H -0.2079 0.3451 0.8608 0.030 Uiso 1 1 calc R U . . .
H10B_1 H -0.0562 0.3839 0.9492 0.030 Uiso 1 1 calc R U . . .
H10C_1 H -0.0806 0.2595 0.8838 0.030 Uiso 1 1 calc R U . . .
C1_2 C 0.1557(3) 0.29334(18) 0.63768(13) 0.0133(4) Uani 1 1 d . . . . .
C2_2 C 0.3175(3) 0.24744(19) 0.64565(14) 0.0169(4) Uani 1 1 d . . . . .
C3_2 C 0.3312(3) 0.1636(2) 0.57464(15) 0.0208(5) Uani 1 1 d . . . . .
H3_2 H 0.4389 0.1325 0.5784 0.025 Uiso 1 1 calc R U . . .
C4_2 C 0.1899(3) 0.12454(19) 0.49822(14) 0.0197(5) Uani 1 1 d . . . . .
C5_2 C 0.0297(3) 0.1715(2) 0.49389(14) 0.0187(5) Uani 1 1 d . . . . .
H5_2 H -0.0664 0.1458 0.4432 0.022 Uiso 1 1 calc R U . . .
C6_2 C 0.0086(3) 0.25574(19) 0.56318(13) 0.0153(4) Uani 1 1 d . . . . .
C7_2 C 0.4739(3) 0.2862(2) 0.72678(15) 0.0222(5) Uani 1 1 d . . . . .
H7A_2 H 0.5702 0.2427 0.7197 0.033 Uiso 1 1 calc R U . . .
H7B_2 H 0.4228 0.2713 0.7716 0.033 Uiso 1 1 calc R U . . .
H7C_2 H 0.5287 0.3696 0.7409 0.033 Uiso 1 1 calc R U . . .
C8_2 C 0.2111(4) 0.0342(2) 0.42292(15) 0.0283(6) Uani 1 1 d . . . . .
H8A_2 H 0.0873 -0.0104 0.3873 0.042 Uiso 1 1 calc R U . . .
H8B_2 H 0.2820 -0.0186 0.4421 0.042 Uiso 1 1 calc R U . . .
H8C_2 H 0.2775 0.0739 0.3912 0.042 Uiso 1 1 calc R U . . .
C9_2 C -0.1686(3) 0.3027(2) 0.55542(14) 0.0201(5) Uani 1 1 d . . . . .
H9A_2 H -0.1415 0.3804 0.5489 0.030 Uiso 1 1 calc R U . . .
H9B_2 H -0.2111 0.3071 0.6057 0.030 Uiso 1 1 calc R U . . .
H9C_2 H -0.2664 0.2504 0.5067 0.030 Uiso 1 1 calc R U . . .
C1_3 C 0.1509(3) 0.68994(18) 0.80805(13) 0.0134(4) Uani 1 1 d . . . . .
C2_3 C 0.0502(3) 0.71881(19) 0.73896(14) 0.0153(4) Uani 1 1 d . . . . .
C3_3 C 0.0684(3) 0.8382(2) 0.74552(14) 0.0191(5) Uani 1 1 d . . . . .
H3_3 H 0.0046 0.8588 0.6996 0.023 Uiso 1 1 calc R U . . .
C4_3 C 0.1782(3) 0.9279(2) 0.81791(15) 0.0202(5) Uani 1 1 d . . . . .
C5_3 C 0.2646(3) 0.8955(2) 0.88704(14) 0.0181(5) Uani 1 1 d . . . . .
H5_3 H 0.3328 0.9549 0.9371 0.022 Uiso 1 1 calc R U . . .
C6_3 C 0.2533(3) 0.77786(19) 0.88439(13) 0.0146(4) Uani 1 1 d . . . . .
C7_3 C -0.0758(3) 0.6269(2) 0.65939(14) 0.0210(5) Uani 1 1 d . . . . .
H7A_3 H -0.1714 0.6605 0.6322 0.032 Uiso 1 1 calc R U . . .
H7B_3 H -0.1361 0.5602 0.6735 0.032 Uiso 1 1 calc R U . . .
H7C_3 H -0.0007 0.6013 0.6216 0.032 Uiso 1 1 calc R U . . .
C8_3 C 0.2014(4) 1.0565(2) 0.82208(18) 0.0311(6) Uani 1 1 d . . . . .
H8A_3 H 0.3196 1.0842 0.8106 0.047 Uiso 1 1 calc R U . . .
H8B_3 H 0.2018 1.1025 0.8777 0.047 Uiso 1 1 calc R U . . .
H8C_3 H 0.0978 1.0649 0.7805 0.047 Uiso 1 1 calc R U . . .
C9_3 C 0.3473(3) 0.7511(2) 0.96356(14) 0.0182(5) Uani 1 1 d . . . . .
H9A_3 H 0.3843 0.6771 0.9480 0.027 Uiso 1 1 calc R U . . .
H9B_3 H 0.2596 0.7458 0.9975 0.027 Uiso 1 1 calc R U . . .
H9C_3 H 0.4581 0.8135 0.9956 0.027 Uiso 1 1 calc R U . . .
Br1_4 Br 0.37411(3) 0.50005(2) 0.58741(2) 0.02169(8) Uani 1 1 d . . . . .
B2_4 B 0.3532(3) 0.5601(2) 0.70127(15) 0.0148(5) Uani 1 1 d . . . . .
C3_4 C 0.4988(3) 0.68079(19) 0.75742(13) 0.0153(4) Uani 1 1 d . . . . .
C4_4 C 0.6133(3) 0.6903(2) 0.83658(14) 0.0167(4) Uani 1 1 d . . . . .
C5_4 C 0.7376(3) 0.7941(2) 0.89022(14) 0.0197(5) Uani 1 1 d . . . . .
C6_4 C 0.7485(3) 0.8945(2) 0.86489(15) 0.0221(5) Uani 1 1 d . . . . .
C7_4 C 0.6394(3) 0.8897(2) 0.78646(15) 0.0219(5) Uani 1 1 d . . . . .
C8_4 C 0.5196(3) 0.7840(2) 0.73366(14) 0.0187(5) Uani 1 1 d . . . . .
F9_4 F 0.59834(18) 0.59482(11) 0.86491(8) 0.0209(3) Uani 1 1 d . . . . .
F10_4 F 0.84002(19) 0.79922(12) 0.96716(8) 0.0257(3) Uani 1 1 d . . . . .
F11_4 F 0.8619(2) 0.99791(12) 0.91714(9) 0.0301(3) Uani 1 1 d . . . . .
F12_4 F 0.6491(2) 0.98878(12) 0.76295(9) 0.0323(4) Uani 1 1 d . . . . .
F13_4 F 0.4138(2) 0.78473(12) 0.65871(8) 0.0244(3) 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
C1_1 N2_1 1.389(3) . ?
C1_1 N6_1 1.403(3) . ?
C1_1 B2_4 1.524(3) . ?
N2_1 C3_1 1.404(3) . ?
N2_1 C1_2 1.460(3) . ?
C3_1 O7_1 1.202(3) . ?
C3_1 C4_1 1.518(3) . ?
C4_1 C5_1 1.507(3) . ?
C4_1 C10_1 1.522(3) . ?
C4_1 C9_1 1.553(3) . ?
C5_1 O8_1 1.207(3) . ?
C5_1 N6_1 1.396(3) . ?
N6_1 C1_3 1.450(3) . ?
C9_1 H9A_1 0.9600 . ?
C9_1 H9B_1 0.9600 . ?
C9_1 H9C_1 0.9600 . ?
C10_1 H10A_1 0.9600 . ?
C10_1 H10B_1 0.9600 . ?
C10_1 H10C_1 0.9600 . ?
C1_2 C6_2 1.389(3) . ?
C1_2 C2_2 1.392(3) . ?
C2_2 C3_2 1.389(3) . ?
C2_2 C7_2 1.499(3) . ?
C3_2 C4_2 1.388(3) . ?
C3_2 H3_2 0.9300 . ?
C4_2 C5_2 1.389(3) . ?
C4_2 C8_2 1.500(3) . ?
C5_2 C6_2 1.393(3) . ?
C5_2 H5_2 0.9300 . ?
C6_2 C9_2 1.502(3) . ?
C7_2 H7A_2 0.9600 . ?
C7_2 H7B_2 0.9600 . ?
C7_2 H7C_2 0.9600 . ?
C8_2 H8A_2 0.9600 . ?
C8_2 H8B_2 0.9600 . ?
C8_2 H8C_2 0.9600 . ?
C9_2 H9A_2 0.9600 . ?
C9_2 H9B_2 0.9600 . ?
C9_2 H9C_2 0.9600 . ?
C1_3 C2_3 1.399(3) . ?
C1_3 C6_3 1.402(3) . ?
C2_3 C3_3 1.388(3) . ?
C2_3 C7_3 1.500(3) . ?
C3_3 C4_3 1.385(3) . ?
C3_3 H3_3 0.9300 . ?
C4_3 C5_3 1.385(3) . ?
C4_3 C8_3 1.503(3) . ?
C5_3 C6_3 1.387(3) . ?
C5_3 H5_3 0.9300 . ?
C6_3 C9_3 1.507(3) . ?
C7_3 H7A_3 0.9600 . ?
C7_3 H7B_3 0.9600 . ?
C7_3 H7C_3 0.9600 . ?
C8_3 H8A_3 0.9600 . ?
C8_3 H8B_3 0.9600 . ?
C8_3 H8C_3 0.9600 . ?
C9_3 H9A_3 0.9600 . ?
C9_3 H9B_3 0.9600 . ?
C9_3 H9C_3 0.9600 . ?
Br1_4 B2_4 1.925(2) . ?
B2_4 C3_4 1.578(3) . ?
C3_4 C4_4 1.387(3) . ?
C3_4 C8_4 1.391(3) . ?
C4_4 F9_4 1.347(3) . ?
C4_4 C5_4 1.377(3) . ?
C5_4 F10_4 1.338(3) . ?
C5_4 C6_4 1.374(3) . ?
C6_4 F11_4 1.339(3) . ?
C6_4 C7_4 1.378(3) . ?
C7_4 F12_4 1.341(3) . ?
C7_4 C8_4 1.376(3) . ?
C8_4 F13_4 1.342(3) . ?

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
N2_1 C1_1 N6_1 115.35(18) . . ?
N2_1 C1_1 B2_4 126.11(18) . . ?
N6_1 C1_1 B2_4 118.53(19) . . ?
C1_1 N2_1 C3_1 123.07(17) . . ?
C1_1 N2_1 C1_2 122.80(17) . . ?
C3_1 N2_1 C1_2 113.90(17) . . ?
O7_1 C3_1 N2_1 120.77(19) . . ?
O7_1 C3_1 C4_1 123.26(19) . . ?
N2_1 C3_1 C4_1 115.89(18) . . ?
C5_1 C4_1 C3_1 108.97(17) . . ?
C5_1 C4_1 C10_1 110.90(18) . . ?
C3_1 C4_1 C10_1 110.75(18) . . ?
C5_1 C4_1 C9_1 108.23(17) . . ?
C3_1 C4_1 C9_1 108.72(17) . . ?
C10_1 C4_1 C9_1 109.21(18) . . ?
O8_1 C5_1 N6_1 121.1(2) . . ?
O8_1 C5_1 C4_1 123.70(19) . . ?
N6_1 C5_1 C4_1 115.20(18) . . ?
C5_1 N6_1 C1_1 123.73(18) . . ?
C5_1 N6_1 C1_3 116.06(17) . . ?
C1_1 N6_1 C1_3 119.52(17) . . ?
C4_1 C9_1 H9A_1 109.5 . . ?
C4_1 C9_1 H9B_1 109.5 . . ?
H9A_1 C9_1 H9B_1 109.5 . . ?
C4_1 C9_1 H9C_1 109.5 . . ?
H9A_1 C9_1 H9C_1 109.5 . . ?
H9B_1 C9_1 H9C_1 109.5 . . ?
C4_1 C10_1 H10A_1 109.5 . . ?
C4_1 C10_1 H10B_1 109.5 . . ?
H10A_1 C10_1 H10B_1 109.5 . . ?
C4_1 C10_1 H10C_1 109.5 . . ?
H10A_1 C10_1 H10C_1 109.5 . . ?
H10B_1 C10_1 H10C_1 109.5 . . ?
C6_2 C1_2 C2_2 122.51(19) . . ?
C6_2 C1_2 N2_1 118.84(19) . . ?
C2_2 C1_2 N2_1 118.40(18) . . ?
C3_2 C2_2 C1_2 117.5(2) . . ?
C3_2 C2_2 C7_2 120.2(2) . . ?
C1_2 C2_2 C7_2 122.3(2) . . ?
C4_2 C3_2 C2_2 122.3(2) . . ?
C4_2 C3_2 H3_2 118.8 . . ?
C2_2 C3_2 H3_2 118.8 . . ?
C3_2 C4_2 C5_2 118.0(2) . . ?
C3_2 C4_2 C8_2 120.6(2) . . ?
C5_2 C4_2 C8_2 121.4(2) . . ?
C4_2 C5_2 C6_2 122.0(2) . . ?
C4_2 C5_2 H5_2 119.0 . . ?
C6_2 C5_2 H5_2 119.0 . . ?
C1_2 C6_2 C5_2 117.6(2) . . ?
C1_2 C6_2 C9_2 122.49(19) . . ?
C5_2 C6_2 C9_2 119.9(2) . . ?
C2_2 C7_2 H7A_2 109.5 . . ?
C2_2 C7_2 H7B_2 109.5 . . ?
H7A_2 C7_2 H7B_2 109.5 . . ?
C2_2 C7_2 H7C_2 109.5 . . ?
H7A_2 C7_2 H7C_2 109.5 . . ?
H7B_2 C7_2 H7C_2 109.5 . . ?
C4_2 C8_2 H8A_2 109.5 . . ?
C4_2 C8_2 H8B_2 109.5 . . ?
H8A_2 C8_2 H8B_2 109.5 . . ?
C4_2 C8_2 H8C_2 109.5 . . ?
H8A_2 C8_2 H8C_2 109.5 . . ?
H8B_2 C8_2 H8C_2 109.5 . . ?
C6_2 C9_2 H9A_2 109.5 . . ?
C6_2 C9_2 H9B_2 109.5 . . ?
H9A_2 C9_2 H9B_2 109.5 . . ?
C6_2 C9_2 H9C_2 109.5 . . ?
H9A_2 C9_2 H9C_2 109.5 . . ?
H9B_2 C9_2 H9C_2 109.5 . . ?
C2_3 C1_3 C6_3 121.4(2) . . ?
C2_3 C1_3 N6_1 119.40(19) . . ?
C6_3 C1_3 N6_1 119.17(18) . . ?
C3_3 C2_3 C1_3 117.8(2) . . ?
C3_3 C2_3 C7_3 119.3(2) . . ?
C1_3 C2_3 C7_3 123.0(2) . . ?
C4_3 C3_3 C2_3 122.4(2) . . ?
C4_3 C3_3 H3_3 118.8 . . ?
C2_3 C3_3 H3_3 118.8 . . ?
C5_3 C4_3 C3_3 117.9(2) . . ?
C5_3 C4_3 C8_3 120.8(2) . . ?
C3_3 C4_3 C8_3 121.3(2) . . ?
C4_3 C5_3 C6_3 122.5(2) . . ?
C4_3 C5_3 H5_3 118.8 . . ?
C6_3 C5_3 H5_3 118.8 . . ?
C5_3 C6_3 C1_3 117.7(2) . . ?
C5_3 C6_3 C9_3 118.7(2) . . ?
C1_3 C6_3 C9_3 123.6(2) . . ?
C2_3 C7_3 H7A_3 109.5 . . ?
C2_3 C7_3 H7B_3 109.5 . . ?
H7A_3 C7_3 H7B_3 109.5 . . ?
C2_3 C7_3 H7C_3 109.5 . . ?
H7A_3 C7_3 H7C_3 109.5 . . ?
H7B_3 C7_3 H7C_3 109.5 . . ?
C4_3 C8_3 H8A_3 109.5 . . ?
C4_3 C8_3 H8B_3 109.5 . . ?
H8A_3 C8_3 H8B_3 109.5 . . ?
C4_3 C8_3 H8C_3 109.5 . . ?
H8A_3 C8_3 H8C_3 109.5 . . ?
H8B_3 C8_3 H8C_3 109.5 . . ?
C6_3 C9_3 H9A_3 109.5 . . ?
C6_3 C9_3 H9B_3 109.5 . . ?
H9A_3 C9_3 H9B_3 109.5 . . ?
C6_3 C9_3 H9C_3 109.5 . . ?
H9A_3 C9_3 H9C_3 109.5 . . ?
H9B_3 C9_3 H9C_3 109.5 . . ?
C1_1 B2_4 C3_4 120.72(19) . . ?
C1_1 B2_4 Br1_4 123.84(17) . . ?
C3_4 B2_4 Br1_4 115.44(16) . . ?
C4_4 C3_4 C8_4 115.4(2) . . ?
C4_4 C3_4 B2_4 120.6(2) . . ?
C8_4 C3_4 B2_4 123.9(2) . . ?
F9_4 C4_4 C5_4 117.4(2) . . ?
F9_4 C4_4 C3_4 118.95(19) . . ?
C5_4 C4_4 C3_4 123.6(2) . . ?
F10_4 C5_4 C6_4 120.1(2) . . ?
F10_4 C5_4 C4_4 121.1(2) . . ?
C6_4 C5_4 C4_4 118.7(2) . . ?
F11_4 C6_4 C5_4 120.1(2) . . ?
F11_4 C6_4 C7_4 119.9(2) . . ?
C5_4 C6_4 C7_4 120.1(2) . . ?
F12_4 C7_4 C8_4 120.7(2) . . ?
F12_4 C7_4 C6_4 119.5(2) . . ?
C8_4 C7_4 C6_4 119.8(2) . . ?
F13_4 C8_4 C7_4 117.3(2) . . ?
F13_4 C8_4 C3_4 120.2(2) . . ?
C7_4 C8_4 C3_4 122.4(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N6_1 C1_1 N2_1 C3_1 -17.1(3) . . . . ?
B2_4 C1_1 N2_1 C3_1 163.54(19) . . . . ?
N6_1 C1_1 N2_1 C1_2 168.67(17) . . . . ?
B2_4 C1_1 N2_1 C1_2 -10.7(3) . . . . ?
C1_1 N2_1 C3_1 O7_1 170.58(19) . . . . ?
C1_2 N2_1 C3_1 O7_1 -14.8(3) . . . . ?
C1_1 N2_1 C3_1 C4_1 -12.6(3) . . . . ?
C1_2 N2_1 C3_1 C4_1 162.08(17) . . . . ?
O7_1 C3_1 C4_1 C5_1 -141.7(2) . . . . ?
N2_1 C3_1 C4_1 C5_1 41.5(2) . . . . ?
O7_1 C3_1 C4_1 C10_1 -19.5(3) . . . . ?
N2_1 C3_1 C4_1 C10_1 163.78(18) . . . . ?
O7_1 C3_1 C4_1 C9_1 100.5(2) . . . . ?
N2_1 C3_1 C4_1 C9_1 -76.2(2) . . . . ?
C3_1 C4_1 C5_1 O8_1 139.1(2) . . . . ?
C10_1 C4_1 C5_1 O8_1 17.0(3) . . . . ?
C9_1 C4_1 C5_1 O8_1 -102.8(2) . . . . ?
C3_1 C4_1 C5_1 N6_1 -43.0(2) . . . . ?
C10_1 C4_1 C5_1 N6_1 -165.13(17) . . . . ?
C9_1 C4_1 C5_1 N6_1 75.1(2) . . . . ?
O8_1 C5_1 N6_1 C1_1 -165.82(19) . . . . ?
C4_1 C5_1 N6_1 C1_1 16.2(3) . . . . ?
O8_1 C5_1 N6_1 C1_3 4.7(3) . . . . ?
C4_1 C5_1 N6_1 C1_3 -173.32(17) . . . . ?
N2_1 C1_1 N6_1 C5_1 15.4(3) . . . . ?
B2_4 C1_1 N6_1 C5_1 -165.24(19) . . . . ?
N2_1 C1_1 N6_1 C1_3 -154.78(18) . . . . ?
B2_4 C1_1 N6_1 C1_3 24.6(3) . . . . ?
C1_1 N2_1 C1_2 C6_2 -99.0(2) . . . . ?
C3_1 N2_1 C1_2 C6_2 86.3(2) . . . . ?
C1_1 N2_1 C1_2 C2_2 86.5(3) . . . . ?
C3_1 N2_1 C1_2 C2_2 -88.2(2) . . . . ?
C6_2 C1_2 C2_2 C3_2 2.0(3) . . . . ?
N2_1 C1_2 C2_2 C3_2 176.21(19) . . . . ?
C6_2 C1_2 C2_2 C7_2 -178.6(2) . . . . ?
N2_1 C1_2 C2_2 C7_2 -4.3(3) . . . . ?
C1_2 C2_2 C3_2 C4_2 -0.7(3) . . . . ?
C7_2 C2_2 C3_2 C4_2 179.8(2) . . . . ?
C2_2 C3_2 C4_2 C5_2 -0.4(3) . . . . ?
C2_2 C3_2 C4_2 C8_2 179.7(2) . . . . ?
C3_2 C4_2 C5_2 C6_2 0.3(3) . . . . ?
C8_2 C4_2 C5_2 C6_2 -179.7(2) . . . . ?
C2_2 C1_2 C6_2 C5_2 -2.0(3) . . . . ?
N2_1 C1_2 C6_2 C5_2 -176.22(19) . . . . ?
C2_2 C1_2 C6_2 C9_2 178.1(2) . . . . ?
N2_1 C1_2 C6_2 C9_2 3.9(3) . . . . ?
C4_2 C5_2 C6_2 C1_2 0.8(3) . . . . ?
C4_2 C5_2 C6_2 C9_2 -179.3(2) . . . . ?
C5_1 N6_1 C1_3 C2_3 -111.8(2) . . . . ?
C1_1 N6_1 C1_3 C2_3 59.1(3) . . . . ?
C5_1 N6_1 C1_3 C6_3 66.6(2) . . . . ?
C1_1 N6_1 C1_3 C6_3 -122.4(2) . . . . ?
C6_3 C1_3 C2_3 C3_3 5.6(3) . . . . ?
N6_1 C1_3 C2_3 C3_3 -175.96(18) . . . . ?
C6_3 C1_3 C2_3 C7_3 -174.0(2) . . . . ?
N6_1 C1_3 C2_3 C7_3 4.4(3) . . . . ?
C1_3 C2_3 C3_3 C4_3 -1.4(3) . . . . ?
C7_3 C2_3 C3_3 C4_3 178.2(2) . . . . ?
C2_3 C3_3 C4_3 C5_3 -3.1(3) . . . . ?
C2_3 C3_3 C4_3 C8_3 177.6(2) . . . . ?
C3_3 C4_3 C5_3 C6_3 3.6(3) . . . . ?
C8_3 C4_3 C5_3 C6_3 -177.2(2) . . . . ?
C4_3 C5_3 C6_3 C1_3 0.5(3) . . . . ?
C4_3 C5_3 C6_3 C9_3 -178.3(2) . . . . ?
C2_3 C1_3 C6_3 C5_3 -5.2(3) . . . . ?
N6_1 C1_3 C6_3 C5_3 176.40(18) . . . . ?
C2_3 C1_3 C6_3 C9_3 173.5(2) . . . . ?
N6_1 C1_3 C6_3 C9_3 -4.9(3) . . . . ?
N2_1 C1_1 B2_4 C3_4 -151.4(2) . . . . ?
N6_1 C1_1 B2_4 C3_4 29.3(3) . . . . ?
N2_1 C1_1 B2_4 Br1_4 27.7(3) . . . . ?
N6_1 C1_1 B2_4 Br1_4 -151.60(16) . . . . ?
C1_1 B2_4 C3_4 C4_4 52.6(3) . . . . ?
Br1_4 B2_4 C3_4 C4_4 -126.61(19) . . . . ?
C1_1 B2_4 C3_4 C8_4 -125.9(2) . . . . ?
Br1_4 B2_4 C3_4 C8_4 55.0(3) . . . . ?
C8_4 C3_4 C4_4 F9_4 178.54(18) . . . . ?
B2_4 C3_4 C4_4 F9_4 0.0(3) . . . . ?
C8_4 C3_4 C4_4 C5_4 1.3(3) . . . . ?
B2_4 C3_4 C4_4 C5_4 -177.3(2) . . . . ?
F9_4 C4_4 C5_4 F10_4 0.4(3) . . . . ?
C3_4 C4_4 C5_4 F10_4 177.69(19) . . . . ?
F9_4 C4_4 C5_4 C6_4 -176.61(19) . . . . ?
C3_4 C4_4 C5_4 C6_4 0.7(3) . . . . ?
F10_4 C5_4 C6_4 F11_4 0.1(3) . . . . ?
C4_4 C5_4 C6_4 F11_4 177.12(19) . . . . ?
F10_4 C5_4 C6_4 C7_4 -178.4(2) . . . . ?
C4_4 C5_4 C6_4 C7_4 -1.4(3) . . . . ?
F11_4 C6_4 C7_4 F12_4 0.5(3) . . . . ?
C5_4 C6_4 C7_4 F12_4 179.0(2) . . . . ?
F11_4 C6_4 C7_4 C8_4 -178.5(2) . . . . ?
C5_4 C6_4 C7_4 C8_4 0.0(3) . . . . ?
F12_4 C7_4 C8_4 F13_4 -0.3(3) . . . . ?
C6_4 C7_4 C8_4 F13_4 178.7(2) . . . . ?
F12_4 C7_4 C8_4 C3_4 -176.9(2) . . . . ?
C6_4 C7_4 C8_4 C3_4 2.1(3) . . . . ?
C4_4 C3_4 C8_4 F13_4 -179.20(19) . . . . ?
B2_4 C3_4 C8_4 F13_4 -0.7(3) . . . . ?
C4_4 C3_4 C8_4 C7_4 -2.7(3) . . . . ?
B2_4 C3_4 C8_4 C7_4 175.8(2) . . . . ?

_refine_diff_density_max         0.654
_refine_diff_density_min         -0.541
_refine_diff_density_rms         0.075

####################################################################### 
# 
# 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_test_a_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1839161'
_audit_update_record             
;
2018-04-24 deposited with the CCDC.
2018-07-04 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C29 H34 B F5 N'
_chemical_formula_sum            'C29 H34 B F5 N'
_chemical_formula_weight         502.38

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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   7.7509(4)
_cell_length_b                   10.5075(7)
_cell_length_c                   31.1985(19)
_cell_angle_alpha                90
_cell_angle_beta                 91.565(2)
_cell_angle_gamma                90
_cell_volume                     2539.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9863
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      26.71


_exptl_special_details           
;
The crystal was immersed in a film of perfluoropolyether oil, mounted on a 
polyimide microloop (MicroMounts of MiTeGen) and transferred to stream of cold 
nitrogen (Bruker Kryoflex2).
;
_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_F_000             1060
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.09
_exptl_absorpt_coefficient_mu    0.101
_shelx_estimated_absorpt_T_min   0.961
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6512
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'SadAbs 2014/5 (Bruker AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'multi-layer mirror'
_diffrn_source                   'microfocus sealed tube (Incoatec ImS)'
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector                 'CMOS area detector (Photon 100)'
_diffrn_detector_area_resol_mean 10.24
_diffrn_reflns_number            37502
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_av_R_equivalents  0.0507
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         2.337
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5185
_reflns_number_gt                3924
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 ver. 2014.9 (Bruker AXS)'
_computing_cell_refinement       'Saint+ ver. V8.34A (Bruker AXS)'
_computing_data_reduction        'Saint+ ver. V8.34A (Bruker AXS)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_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     
'w=1/[σ²(Fo²)+(0.0563P)²+2.2079P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5185
_refine_ls_number_parameters     336
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0790
_refine_ls_R_factor_gt           0.0524
_refine_ls_wR_factor_ref         0.1369
_refine_ls_wR_factor_gt          0.1205
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_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_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
F001 F 0.50152(15) 0.77258(11) 0.55547(4) 0.0251(3) Uani 1 1 d . . . . .
H1 H 0.572(3) 0.840(2) 0.6386(7) 0.023(6) Uiso 1 1 d . . . . .
F002 F 0.66703(15) 0.49313(12) 0.66877(4) 0.0262(3) Uani 1 1 d . . . . .
F003 F 0.81491(16) 0.34199(12) 0.61294(4) 0.0332(3) Uani 1 1 d . . . . .
F004 F 0.64176(18) 0.61340(14) 0.49951(4) 0.0368(4) Uani 1 1 d . . . . .
F005 F 0.80190(18) 0.39639(14) 0.52738(5) 0.0410(4) Uani 1 1 d . . . . .
N006 N 0.23368(19) 0.89467(15) 0.65019(5) 0.0137(3) Uani 1 1 d . . . . .
C007 C 0.2925(2) 0.78472(18) 0.63757(6) 0.0148(4) Uani 1 1 d . . . . .
C008 C 0.3480(2) 0.98695(18) 0.67149(6) 0.0145(4) Uani 1 1 d . . . . .
C009 C 0.5710(2) 0.64049(19) 0.61510(6) 0.0173(4) Uani 1 1 d . . . . .
C00A C 0.4235(2) 0.94989(19) 0.71109(6) 0.0167(4) Uani 1 1 d . . . . .
C00B C 0.1428(2) 0.69914(19) 0.62428(6) 0.0182(4) Uani 1 1 d . . . . .
C00C C 0.3893(2) 1.10121(19) 0.65149(6) 0.0176(4) Uani 1 1 d . . . . .
C00D C 0.6536(2) 0.52923(19) 0.62689(6) 0.0187(4) Uani 1 1 d . . . . .
C00E C 0.0372(2) 0.9062(2) 0.65144(6) 0.0181(4) Uani 1 1 d . . . . .
C00F C 0.5095(3) 0.7220(2) 0.69884(6) 0.0197(4) Uani 1 1 d . . . . .
H00A H 0.4708 0.6338 0.7042 0.024 Uiso 1 1 calc R U . . .
H00B H 0.6324 0.7279 0.7082 0.024 Uiso 1 1 calc R U . . .
C00G C -0.0186(3) 0.8995(2) 0.69819(7) 0.0233(5) Uani 1 1 d . . . . .
H00C H -0.1435 0.9129 0.6994 0.035 Uiso 1 1 calc R U . . .
H00D H 0.0415 0.9655 0.7150 0.035 Uiso 1 1 calc R U . . .
H00E H 0.0105 0.8156 0.7101 0.035 Uiso 1 1 calc R U . . .
C00H C 0.4972(3) 1.1853(2) 0.67430(6) 0.0221(4) Uani 1 1 d . . . . .
H00H H 0.5238 1.2655 0.6621 0.026 Uiso 1 1 calc R U . . .
C00I C 0.5315(2) 1.0365(2) 0.73222(6) 0.0210(4) Uani 1 1 d . . . . .
H00I H 0.5825 1.0148 0.7593 0.025 Uiso 1 1 calc R U . . .
C00J C 0.4025(3) 0.8142(2) 0.72673(6) 0.0193(4) Uani 1 1 d . . . . .
H00J H 0.2784 0.7912 0.7217 0.023 Uiso 1 1 calc R U . . .
C00K C 0.5744(2) 0.66428(19) 0.57135(7) 0.0200(4) Uani 1 1 d . . . . .
C00L C 0.3416(3) 1.1318(2) 0.60488(6) 0.0202(4) Uani 1 1 d . . . . .
H00L H 0.2531 1.0688 0.5946 0.024 Uiso 1 1 calc R U . . .
C00M C -0.0331(3) 1.0284(2) 0.63173(7) 0.0225(5) Uani 1 1 d . . . . .
H00F H -0.0029 1.0323 0.6015 0.034 Uiso 1 1 calc R U . . .
H00G H 0.0173 1.1016 0.6470 0.034 Uiso 1 1 calc R U . . .
H00K H -0.1589 1.0301 0.6340 0.034 Uiso 1 1 calc R U . . .
C00N C 0.5657(3) 1.1539(2) 0.71423(7) 0.0236(5) Uani 1 1 d . . . . .
H00N H 0.6367 1.2132 0.7294 0.028 Uiso 1 1 calc R U . . .
C00O C 0.6471(3) 0.5842(2) 0.54158(6) 0.0243(5) Uani 1 1 d . . . . .
C00P C 0.1344(3) 0.5902(2) 0.65731(7) 0.0239(5) Uani 1 1 d . . . . .
H00M H 0.0354 0.5353 0.6502 0.036 Uiso 1 1 calc R U . . .
H00O H 0.1216 0.6260 0.6860 0.036 Uiso 1 1 calc R U . . .
H00P H 0.2408 0.5400 0.6566 0.036 Uiso 1 1 calc R U . . .
C00Q C 0.1594(3) 0.6404(2) 0.57960(6) 0.0233(5) Uani 1 1 d . . . . .
H00Q H 0.1827 0.7078 0.5588 0.035 Uiso 1 1 calc R U . . .
H00R H 0.0516 0.5971 0.5714 0.035 Uiso 1 1 calc R U . . .
H00S H 0.2546 0.5790 0.5801 0.035 Uiso 1 1 calc R U . . .
C00R C 0.7315(3) 0.4472(2) 0.59860(7) 0.0235(5) Uani 1 1 d . . . . .
C00S C -0.0152(3) 0.7886(2) 0.62529(7) 0.0228(5) Uani 1 1 d . . . . .
H00T H -0.0510 0.8136 0.5958 0.027 Uiso 1 1 calc R U . . .
H00U H -0.1133 0.7449 0.6387 0.027 Uiso 1 1 calc R U . . .
C00T C 0.7272(3) 0.4743(2) 0.55557(7) 0.0257(5) Uani 1 1 d . . . . .
C00U C 0.5021(3) 1.1160(2) 0.57776(7) 0.0257(5) Uani 1 1 d . . . . .
H00V H 0.4729 1.1365 0.5478 0.038 Uiso 1 1 calc R U . . .
H00W H 0.5430 1.0279 0.5797 0.038 Uiso 1 1 calc R U . . .
H00X H 0.5931 1.1735 0.5884 0.038 Uiso 1 1 calc R U . . .
C00V C 0.8352(3) -0.0429(2) 0.50790(7) 0.0303(5) Uani 1 1 d . . . . .
H00Y H 0.7222 -0.0724 0.5135 0.036 Uiso 1 1 calc R U . . .
C00W C 1.0343(3) 0.1294(2) 0.49991(7) 0.0304(5) Uani 1 1 d . . . . .
H00Z H 1.0580 0.2181 0.5000 0.036 Uiso 1 1 calc R U . . .
C00X C 0.4416(3) 0.7954(2) 0.77449(6) 0.0282(5) Uani 1 1 d . . . . .
H010 H 0.4166 0.7072 0.7824 0.042 Uiso 1 1 calc R U . . .
H011 H 0.3697 0.8531 0.7910 0.042 Uiso 1 1 calc R U . . .
H012 H 0.5637 0.8138 0.7807 0.042 Uiso 1 1 calc R U . . .
C00Y C 0.2655(3) 1.2657(2) 0.59924(7) 0.0289(5) Uani 1 1 d . . . . .
H013 H 0.2241 1.2768 0.5695 0.043 Uiso 1 1 calc R U . . .
H014 H 0.3546 1.3292 0.6060 0.043 Uiso 1 1 calc R U . . .
H015 H 0.1690 1.2765 0.6186 0.043 Uiso 1 1 calc R U . . .
C00Z C 0.8692(3) 0.0860(2) 0.50756(7) 0.0318(5) Uani 1 1 d . . . . .
H016 H 0.7792 0.1451 0.5126 0.038 Uiso 1 1 calc R U . . .
B010 B 0.4941(3) 0.7504(2) 0.64675(7) 0.0167(5) 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
F001 C00K 1.358(2) . ?
F002 C00D 1.362(2) . ?
F003 C00R 1.351(2) . ?
F004 C00O 1.348(2) . ?
F005 C00T 1.344(2) . ?
N006 C007 1.307(2) . ?
N006 C008 1.461(2) . ?
N006 C00E 1.529(2) . ?
C007 C00B 1.517(3) . ?
C007 B010 1.621(3) . ?
C008 C00C 1.394(3) . ?
C008 C00A 1.407(3) . ?
C009 C00D 1.378(3) . ?
C009 C00K 1.388(3) . ?
C009 B010 1.642(3) . ?
C00A C00I 1.390(3) . ?
C00A C00J 1.517(3) . ?
C00B C00Q 1.533(3) . ?
C00B C00P 1.543(3) . ?
C00B C00S 1.544(3) . ?
C00C C00H 1.398(3) . ?
C00C C00L 1.525(3) . ?
C00D C00R 1.384(3) . ?
C00E C00M 1.518(3) . ?
C00E C00S 1.530(3) . ?
C00E C00G 1.534(3) . ?
C00F C00J 1.556(3) . ?
C00F B010 1.654(3) . ?
C00F H00A 0.9900 . ?
C00F H00B 0.9900 . ?
C00G H00C 0.9800 . ?
C00G H00D 0.9800 . ?
C00G H00E 0.9800 . ?
C00H C00N 1.381(3) . ?
C00H H00H 0.9500 . ?
C00I C00N 1.384(3) . ?
C00I H00I 0.9500 . ?
C00J C00X 1.525(3) . ?
C00J H00J 1.0000 . ?
C00K C00O 1.384(3) . ?
C00L C00U 1.532(3) . ?
C00L C00Y 1.533(3) . ?
C00L H00L 1.0000 . ?
C00M H00F 0.9800 . ?
C00M H00G 0.9800 . ?
C00M H00K 0.9800 . ?
C00N H00N 0.9500 . ?
C00O C00T 1.376(3) . ?
C00P H00M 0.9800 . ?
C00P H00O 0.9800 . ?
C00P H00P 0.9800 . ?
C00Q H00Q 0.9800 . ?
C00Q H00R 0.9800 . ?
C00Q H00S 0.9800 . ?
C00R C00T 1.372(3) . ?
C00S H00T 0.9900 . ?
C00S H00U 0.9900 . ?
C00U H00V 0.9800 . ?
C00U H00W 0.9800 . ?
C00U H00X 0.9800 . ?
C00V C00Z 1.380(3) . ?
C00V C00W 1.386(3) 3_756 ?
C00V H00Y 0.9500 . ?
C00W C00Z 1.385(3) . ?
C00W C00V 1.386(3) 3_756 ?
C00W H00Z 0.9500 . ?
C00X H010 0.9800 . ?
C00X H011 0.9800 . ?
C00X H012 0.9800 . ?
C00Y H013 0.9800 . ?
C00Y H014 0.9800 . ?
C00Y H015 0.9800 . ?
C00Z H016 0.9500 . ?
B010 H1 1.15(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
C007 N006 C008 120.76(15) . . ?
C007 N006 C00E 115.69(15) . . ?
C008 N006 C00E 121.86(15) . . ?
N006 C007 C00B 109.61(16) . . ?
N006 C007 B010 119.08(16) . . ?
C00B C007 B010 130.01(17) . . ?
C00C C008 C00A 122.41(17) . . ?
C00C C008 N006 120.77(16) . . ?
C00A C008 N006 116.62(17) . . ?
C00D C009 C00K 113.22(18) . . ?
C00D C009 B010 127.57(17) . . ?
C00K C009 B010 118.77(18) . . ?
C00I C00A C008 117.76(18) . . ?
C00I C00A C00J 122.07(17) . . ?
C008 C00A C00J 119.78(17) . . ?
C007 C00B C00Q 113.83(16) . . ?
C007 C00B C00P 107.65(16) . . ?
C00Q C00B C00P 108.36(17) . . ?
C007 C00B C00S 103.59(16) . . ?
C00Q C00B C00S 110.47(16) . . ?
C00P C00B C00S 112.95(17) . . ?
C008 C00C C00H 117.26(18) . . ?
C008 C00C C00L 123.77(17) . . ?
C00H C00C C00L 118.56(18) . . ?
F002 C00D C009 121.01(17) . . ?
F002 C00D C00R 114.54(18) . . ?
C009 C00D C00R 124.44(19) . . ?
C00M C00E N006 113.76(16) . . ?
C00M C00E C00S 112.34(16) . . ?
N006 C00E C00S 99.94(15) . . ?
C00M C00E C00G 108.46(17) . . ?
N006 C00E C00G 109.11(15) . . ?
C00S C00E C00G 113.10(17) . . ?
C00J C00F B010 114.35(16) . . ?
C00J C00F H00A 108.7 . . ?
B010 C00F H00A 108.7 . . ?
C00J C00F H00B 108.7 . . ?
B010 C00F H00B 108.7 . . ?
H00A C00F H00B 107.6 . . ?
C00E C00G H00C 109.5 . . ?
C00E C00G H00D 109.5 . . ?
H00C C00G H00D 109.5 . . ?
C00E C00G H00E 109.5 . . ?
H00C C00G H00E 109.5 . . ?
H00D C00G H00E 109.5 . . ?
C00N C00H C00C 121.2(2) . . ?
C00N C00H H00H 119.4 . . ?
C00C C00H H00H 119.4 . . ?
C00N C00I C00A 120.70(18) . . ?
C00N C00I H00I 119.7 . . ?
C00A C00I H00I 119.7 . . ?
C00A C00J C00X 114.55(17) . . ?
C00A C00J C00F 109.98(16) . . ?
C00X C00J C00F 111.79(16) . . ?
C00A C00J H00J 106.7 . . ?
C00X C00J H00J 106.7 . . ?
C00F C00J H00J 106.7 . . ?
F001 C00K C00O 115.95(18) . . ?
F001 C00K C009 119.39(18) . . ?
C00O C00K C009 124.7(2) . . ?
C00C C00L C00U 108.93(16) . . ?
C00C C00L C00Y 112.66(17) . . ?
C00U C00L C00Y 110.61(17) . . ?
C00C C00L H00L 108.2 . . ?
C00U C00L H00L 108.2 . . ?
C00Y C00L H00L 108.2 . . ?
C00E C00M H00F 109.5 . . ?
C00E C00M H00G 109.5 . . ?
H00F C00M H00G 109.5 . . ?
C00E C00M H00K 109.5 . . ?
H00F C00M H00K 109.5 . . ?
H00G C00M H00K 109.5 . . ?
C00H C00N C00I 120.37(19) . . ?
C00H C00N H00N 119.8 . . ?
C00I C00N H00N 119.8 . . ?
F004 C00O C00T 120.10(19) . . ?
F004 C00O C00K 120.8(2) . . ?
C00T C00O C00K 119.06(19) . . ?
C00B C00P H00M 109.5 . . ?
C00B C00P H00O 109.5 . . ?
H00M C00P H00O 109.5 . . ?
C00B C00P H00P 109.5 . . ?
H00M C00P H00P 109.5 . . ?
H00O C00P H00P 109.5 . . ?
C00B C00Q H00Q 109.5 . . ?
C00B C00Q H00R 109.5 . . ?
H00Q C00Q H00R 109.5 . . ?
C00B C00Q H00S 109.5 . . ?
H00Q C00Q H00S 109.5 . . ?
H00R C00Q H00S 109.5 . . ?
F003 C00R C00T 119.49(19) . . ?
F003 C00R C00D 120.8(2) . . ?
C00T C00R C00D 119.7(2) . . ?
C00E C00S C00B 107.65(16) . . ?
C00E C00S H00T 110.2 . . ?
C00B C00S H00T 110.2 . . ?
C00E C00S H00U 110.2 . . ?
C00B C00S H00U 110.2 . . ?
H00T C00S H00U 108.5 . . ?
F005 C00T C00R 121.0(2) . . ?
F005 C00T C00O 120.1(2) . . ?
C00R C00T C00O 118.87(19) . . ?
C00L C00U H00V 109.5 . . ?
C00L C00U H00W 109.5 . . ?
H00V C00U H00W 109.5 . . ?
C00L C00U H00X 109.5 . . ?
H00V C00U H00X 109.5 . . ?
H00W C00U H00X 109.5 . . ?
C00Z C00V C00W 120.1(2) . 3_756 ?
C00Z C00V H00Y 119.9 . . ?
C00W C00V H00Y 119.9 3_756 . ?
C00Z C00W C00V 119.7(2) . 3_756 ?
C00Z C00W H00Z 120.1 . . ?
C00V C00W H00Z 120.1 3_756 . ?
C00J C00X H010 109.5 . . ?
C00J C00X H011 109.5 . . ?
H010 C00X H011 109.5 . . ?
C00J C00X H012 109.5 . . ?
H010 C00X H012 109.5 . . ?
H011 C00X H012 109.5 . . ?
C00L C00Y H013 109.5 . . ?
C00L C00Y H014 109.5 . . ?
H013 C00Y H014 109.5 . . ?
C00L C00Y H015 109.5 . . ?
H013 C00Y H015 109.5 . . ?
H014 C00Y H015 109.5 . . ?
C00V C00Z C00W 120.1(2) . . ?
C00V C00Z H016 119.9 . . ?
C00W C00Z H016 119.9 . . ?
C007 B010 C009 114.48(16) . . ?
C007 B010 C00F 104.89(15) . . ?
C009 B010 C00F 116.53(17) . . ?
C007 B010 H1 106.6(11) . . ?
C009 B010 H1 104.1(11) . . ?
C00F B010 H1 109.9(11) . . ?

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
C008 N006 C007 C00B 169.51(15) . . . . ?
C00E N006 C007 C00B 4.0(2) . . . . ?
C008 N006 C007 B010 1.3(2) . . . . ?
C00E N006 C007 B010 -164.23(16) . . . . ?
C007 N006 C008 C00C 112.2(2) . . . . ?
C00E N006 C008 C00C -83.3(2) . . . . ?
C007 N006 C008 C00A -62.9(2) . . . . ?
C00E N006 C008 C00A 101.7(2) . . . . ?
C00C C008 C00A C00I 5.6(3) . . . . ?
N006 C008 C00A C00I -179.41(16) . . . . ?
C00C C008 C00A C00J -167.30(17) . . . . ?
N006 C008 C00A C00J 7.7(2) . . . . ?
N006 C007 C00B C00Q 128.19(18) . . . . ?
B010 C007 C00B C00Q -65.2(3) . . . . ?
N006 C007 C00B C00P -111.68(18) . . . . ?
B010 C007 C00B C00P 54.9(2) . . . . ?
N006 C007 C00B C00S 8.2(2) . . . . ?
B010 C007 C00B C00S 174.74(18) . . . . ?
C00A C008 C00C C00H -6.2(3) . . . . ?
N006 C008 C00C C00H 178.97(17) . . . . ?
C00A C008 C00C C00L 166.22(18) . . . . ?
N006 C008 C00C C00L -8.6(3) . . . . ?
C00K C009 C00D F002 178.03(16) . . . . ?
B010 C009 C00D F002 5.8(3) . . . . ?
C00K C009 C00D C00R -0.6(3) . . . . ?
B010 C009 C00D C00R -172.78(19) . . . . ?
C007 N006 C00E C00M -134.23(18) . . . . ?
C008 N006 C00E C00M 60.5(2) . . . . ?
C007 N006 C00E C00S -14.3(2) . . . . ?
C008 N006 C00E C00S -179.62(16) . . . . ?
C007 N006 C00E C00G 104.53(19) . . . . ?
C008 N006 C00E C00G -60.8(2) . . . . ?
C008 C00C C00H C00N 2.7(3) . . . . ?
C00L C00C C00H C00N -170.19(19) . . . . ?
C008 C00A C00I C00N -1.3(3) . . . . ?
C00J C00A C00I C00N 171.43(18) . . . . ?
C00I C00A C00J C00X 24.7(3) . . . . ?
C008 C00A C00J C00X -162.68(18) . . . . ?
C00I C00A C00J C00F -102.1(2) . . . . ?
C008 C00A C00J C00F 70.4(2) . . . . ?
B010 C00F C00J C00A -43.5(2) . . . . ?
B010 C00F C00J C00X -171.95(17) . . . . ?
C00D C009 C00K F001 -178.32(16) . . . . ?
B010 C009 C00K F001 -5.4(3) . . . . ?
C00D C009 C00K C00O 2.1(3) . . . . ?
B010 C009 C00K C00O 175.01(19) . . . . ?
C008 C00C C00L C00U -102.7(2) . . . . ?
C00H C00C C00L C00U 69.7(2) . . . . ?
C008 C00C C00L C00Y 134.2(2) . . . . ?
C00H C00C C00L C00Y -53.5(2) . . . . ?
C00C C00H C00N C00I 1.4(3) . . . . ?
C00A C00I C00N C00H -2.1(3) . . . . ?
F001 C00K C00O F004 -1.0(3) . . . . ?
C009 C00K C00O F004 178.67(18) . . . . ?
F001 C00K C00O C00T 178.36(17) . . . . ?
C009 C00K C00O C00T -2.0(3) . . . . ?
F002 C00D C00R F003 -0.9(3) . . . . ?
C009 C00D C00R F003 177.77(17) . . . . ?
F002 C00D C00R C00T -179.61(17) . . . . ?
C009 C00D C00R C00T -0.9(3) . . . . ?
C00M C00E C00S C00B 139.16(17) . . . . ?
N006 C00E C00S C00B 18.2(2) . . . . ?
C00G C00E C00S C00B -97.65(19) . . . . ?
C007 C00B C00S C00E -17.0(2) . . . . ?
C00Q C00B C00S C00E -139.24(17) . . . . ?
C00P C00B C00S C00E 99.2(2) . . . . ?
F003 C00R C00T F005 1.2(3) . . . . ?
C00D C00R C00T F005 179.94(18) . . . . ?
F003 C00R C00T C00O -177.68(18) . . . . ?
C00D C00R C00T C00O 1.0(3) . . . . ?
F004 C00O C00T F005 0.7(3) . . . . ?
C00K C00O C00T F005 -178.59(18) . . . . ?
F004 C00O C00T C00R 179.65(18) . . . . ?
C00K C00O C00T C00R 0.3(3) . . . . ?
C00W C00V C00Z C00W -0.8(4) 3_756 . . . ?
C00V C00W C00Z C00V 0.8(4) 3_756 . . . ?
N006 C007 B010 C009 -157.92(17) . . . . ?
C00B C007 B010 C009 36.6(3) . . . . ?
N006 C007 B010 C00F 73.1(2) . . . . ?
C00B C007 B010 C00F -92.4(2) . . . . ?
C00D C009 B010 C007 -125.7(2) . . . . ?
C00K C009 B010 C007 62.4(2) . . . . ?
C00D C009 B010 C00F -2.9(3) . . . . ?
C00K C009 B010 C00F -174.69(17) . . . . ?
C00J C00F B010 C007 -40.3(2) . . . . ?
C00J C00F B010 C009 -168.06(16) . . . . ?

_refine_diff_density_max         0.268
_refine_diff_density_min         -0.412
_refine_diff_density_rms         0.090

