# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3a
_database_code_depnum_ccdc_archive 'CCDC 1437953'
_audit_update_record             
;
2015-11-20 deposited with the CCDC.
2016-03-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H36 Br5 N2 Ta'
_chemical_formula_weight         969.08

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ta Ta -0.7052 6.5227 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

loop_
_symmetry_equiv_pos_as_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                   10.232(3)
_cell_length_b                   17.868(5)
_cell_length_c                   17.892(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.018(3)
_cell_angle_gamma                90.00
_cell_volume                     3159.3(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9861
_cell_measurement_theta_min      2.2795
_cell_measurement_theta_max      27.0935

_exptl_crystal_description       plate
_exptl_crystal_colour            bright-orange
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.037
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1840
_exptl_absorpt_coefficient_mu    9.822
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.2212
_exptl_absorpt_correction_T_max  0.3401
_exptl_absorpt_process_details   
; 
 Data were corrected for Lorentz polarization and absorption
 effects (empirical absorption correction SADABS).
 R(int) =  0.1716 (selected reflections only, before parameter refinement)
 R(int) =  0.0808 (selected reflections only, after parameter refinement)
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            29725
_diffrn_reflns_av_R_equivalents  0.0727
_diffrn_reflns_av_unetI/netI     0.0543
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.64
_diffrn_reflns_theta_max         26.00
_reflns_number_total             6217
_reflns_number_gt                5080
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1996)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0369P)²+69.7282P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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         6217
_refine_ls_number_parameters     316
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0766
_refine_ls_R_factor_gt           0.0581
_refine_ls_wR_factor_ref         0.1413
_refine_ls_wR_factor_gt          0.1315
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_restrained_S_all      1.101
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ta1 Ta 0.94866(4) 0.81240(2) 0.68759(2) 0.02137(13) Uani 1 1 d . . .
Br1 Br 1.03750(12) 0.89538(7) 0.80347(7) 0.0360(3) Uani 1 1 d . . .
Br2 Br 0.84011(16) 0.92326(8) 0.62085(8) 0.0500(4) Uani 1 1 d . . .
Br3 Br 1.14955(12) 0.83319(7) 0.63642(7) 0.0383(3) Uani 1 1 d . . .
Br4 Br 1.05987(11) 0.70535(6) 0.76401(6) 0.0273(2) Uani 1 1 d . . .
Br5 Br 0.73336(11) 0.77893(7) 0.71842(6) 0.0321(3) Uani 1 1 d . . .
N1 N 0.8848(8) 0.6614(5) 0.5669(4) 0.0189(17) Uani 1 1 d . . .
N2 N 0.7996(8) 0.7588(5) 0.5020(5) 0.0216(18) Uani 1 1 d . . .
C1 C 0.8720(10) 0.7361(6) 0.5755(5) 0.020(2) Uani 1 1 d . . .
C2 C 0.8238(12) 0.6393(7) 0.4913(6) 0.032(3) Uani 1 1 d . . .
H2 H 0.8195 0.5899 0.4712 0.039 Uiso 1 1 calc R . .
C3 C 0.7735(11) 0.6997(6) 0.4532(6) 0.029(2) Uani 1 1 d . . .
H3 H 0.7265 0.7017 0.3999 0.035 Uiso 1 1 calc R . .
C4 C 0.9509(9) 0.6032(5) 0.6186(5) 0.019(2) Uani 1 1 d . . .
C5 C 0.8724(12) 0.5613(6) 0.6575(6) 0.027(2) Uani 1 1 d . . .
C6 C 0.9329(14) 0.4975(7) 0.6975(6) 0.039(3) Uani 1 1 d . . .
H6 H 0.8831 0.4666 0.7235 0.047 Uiso 1 1 calc R . .
C7 C 1.0646(15) 0.4797(7) 0.6993(6) 0.045(4) Uani 1 1 d . . .
H7 H 1.1051 0.4369 0.7275 0.055 Uiso 1 1 calc R . .
C8 C 1.1376(13) 0.5216(7) 0.6619(6) 0.037(3) Uani 1 1 d . . .
H8 H 1.2283 0.5076 0.6645 0.044 Uiso 1 1 calc R . .
C9 C 1.0836(11) 0.5846(6) 0.6198(6) 0.027(2) Uani 1 1 d . . .
C10 C 0.7259(11) 0.5828(6) 0.6535(6) 0.028(2) Uani 1 1 d . . .
H10 H 0.7132 0.6362 0.6363 0.034 Uiso 1 1 calc R . .
C11 C 0.6259(12) 0.5354(8) 0.5934(7) 0.042(3) Uani 1 1 d . . .
H11A H 0.6470 0.5398 0.5432 0.063 Uiso 1 1 calc R . .
H11B H 0.5336 0.5531 0.5888 0.063 Uiso 1 1 calc R . .
H11C H 0.6333 0.4829 0.6098 0.063 Uiso 1 1 calc R . .
C12 C 0.6975(14) 0.5779(7) 0.7329(7) 0.044(3) Uani 1 1 d . . .
H12A H 0.6036 0.5927 0.7287 0.066 Uiso 1 1 calc R . .
H12B H 0.7588 0.6116 0.7690 0.066 Uiso 1 1 calc R . .
H12C H 0.7117 0.5264 0.7522 0.066 Uiso 1 1 calc R . .
C13 C 1.1664(11) 0.6305(7) 0.5774(7) 0.035(3) Uani 1 1 d . . .
H13 H 1.1155 0.6777 0.5594 0.042 Uiso 1 1 calc R . .
C14 C 1.3047(13) 0.6521(9) 0.6296(9) 0.056(4) Uani 1 1 d . . .
H14A H 1.3544 0.6816 0.5999 0.084 Uiso 1 1 calc R . .
H14B H 1.3560 0.6066 0.6490 0.084 Uiso 1 1 calc R . .
H14C H 1.2924 0.6817 0.6733 0.084 Uiso 1 1 calc R . .
C15 C 1.1829(16) 0.5878(9) 0.5051(8) 0.056(4) Uani 1 1 d . . .
H15A H 1.2362 0.6181 0.4781 0.085 Uiso 1 1 calc R . .
H15B H 1.0935 0.5779 0.4702 0.085 Uiso 1 1 calc R . .
H15C H 1.2295 0.5402 0.5210 0.085 Uiso 1 1 calc R . .
C16 C 0.7549(10) 0.8313(6) 0.4686(6) 0.022(2) Uani 1 1 d . . .
C17 C 0.6278(11) 0.8556(6) 0.4698(5) 0.026(2) Uani 1 1 d . . .
C18 C 0.5875(12) 0.9234(7) 0.4328(7) 0.038(3) Uani 1 1 d . . .
H18 H 0.5012 0.9435 0.4323 0.046 Uiso 1 1 calc R . .
C19 C 0.6717(15) 0.9625(7) 0.3965(6) 0.041(3) Uani 1 1 d . . .
H19 H 0.6423 1.0087 0.3716 0.050 Uiso 1 1 calc R . .
C20 C 0.7972(13) 0.9346(7) 0.3964(6) 0.037(3) Uani 1 1 d . . .
H20 H 0.8534 0.9617 0.3712 0.045 Uiso 1 1 calc R . .
C21 C 0.8416(11) 0.8685(6) 0.4321(6) 0.028(2) Uani 1 1 d . . .
C22 C 0.5345(11) 0.8118(7) 0.5075(7) 0.036(3) Uani 1 1 d . . .
H22 H 0.5899 0.7730 0.5419 0.043 Uiso 1 1 calc R . .
C23 C 0.4267(13) 0.7713(8) 0.4451(8) 0.047(3) Uani 1 1 d . . .
H23A H 0.3688 0.7416 0.4697 0.070 Uiso 1 1 calc R . .
H23B H 0.4710 0.7381 0.4155 0.070 Uiso 1 1 calc R . .
H23C H 0.3715 0.8082 0.4102 0.070 Uiso 1 1 calc R . .
C24 C 0.4695(12) 0.8618(8) 0.5573(7) 0.043(3) Uani 1 1 d . . .
H24A H 0.5404 0.8865 0.5970 0.064 Uiso 1 1 calc R . .
H24B H 0.4134 0.8311 0.5823 0.064 Uiso 1 1 calc R . .
H24C H 0.4129 0.8996 0.5245 0.064 Uiso 1 1 calc R . .
C25 C 0.9771(13) 0.8372(7) 0.4278(7) 0.038(3) Uani 1 1 d . . .
H25 H 1.0052 0.7987 0.4694 0.046 Uiso 1 1 calc R . .
C26 C 1.0880(14) 0.8955(9) 0.4400(8) 0.058(4) Uani 1 1 d . . .
H26A H 1.1726 0.8717 0.4368 0.087 Uiso 1 1 calc R . .
H26B H 1.1004 0.9185 0.4911 0.087 Uiso 1 1 calc R . .
H26C H 1.0627 0.9341 0.4000 0.087 Uiso 1 1 calc R . .
C27 C 0.9616(15) 0.7975(10) 0.3483(8) 0.058(4) Uani 1 1 d . . .
H27A H 1.0491 0.7768 0.3459 0.087 Uiso 1 1 calc R . .
H27B H 0.9306 0.8337 0.3063 0.087 Uiso 1 1 calc R . .
H27C H 0.8953 0.7569 0.3427 0.087 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ta1 C1 2.383(10) . ?
Ta1 Br2 2.4281(15) . ?
Ta1 Br4 2.4529(12) . ?
Ta1 Br5 2.4788(12) . ?
Ta1 Br3 2.4852(13) . ?
Ta1 Br1 2.5193(13) . ?
N1 C1 1.354(13) . ?
N1 C2 1.392(13) . ?
N1 C4 1.439(12) . ?
N2 C3 1.352(14) . ?
N2 C1 1.392(12) . ?
N2 C16 1.450(13) . ?
C2 C3 1.308(16) . ?
C2 H2 0.9500 . ?
C3 H3 0.9500 . ?
C4 C9 1.393(14) . ?
C4 C5 1.406(15) . ?
C5 C6 1.403(16) . ?
C5 C10 1.531(15) . ?
C6 C7 1.376(19) . ?
C6 H6 0.9500 . ?
C7 C8 1.351(19) . ?
C7 H7 0.9500 . ?
C8 C9 1.386(16) . ?
C8 H8 0.9500 . ?
C9 C13 1.516(17) . ?
C10 C12 1.525(14) . ?
C10 C11 1.534(16) . ?
C10 H10 1.0000 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.528(16) . ?
C13 C15 1.550(16) . ?
C13 H13 1.0000 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.376(15) . ?
C16 C21 1.398(14) . ?
C17 C18 1.392(17) . ?
C17 C22 1.521(16) . ?
C18 C19 1.394(18) . ?
C18 H18 0.9500 . ?
C19 C20 1.377(18) . ?
C19 H19 0.9500 . ?
C20 C21 1.365(17) . ?
C20 H20 0.9500 . ?
C21 C25 1.514(17) . ?
C22 C24 1.531(16) . ?
C22 C23 1.532(17) . ?
C22 H22 1.0000 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 C26 1.514(17) . ?
C25 C27 1.562(17) . ?
C25 H25 1.0000 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Ta1 Br2 92.5(2) . . ?
C1 Ta1 Br4 91.5(2) . . ?
Br2 Ta1 Br4 175.77(4) . . ?
C1 Ta1 Br5 86.1(2) . . ?
Br2 Ta1 Br5 89.23(5) . . ?
Br4 Ta1 Br5 89.91(4) . . ?
C1 Ta1 Br3 84.2(2) . . ?
Br2 Ta1 Br3 90.77(5) . . ?
Br4 Ta1 Br3 90.77(4) . . ?
Br5 Ta1 Br3 170.26(4) . . ?
C1 Ta1 Br1 177.5(2) . . ?
Br2 Ta1 Br1 86.91(5) . . ?
Br4 Ta1 Br1 89.07(4) . . ?
Br5 Ta1 Br1 96.36(4) . . ?
Br3 Ta1 Br1 93.37(5) . . ?
C1 N1 C2 111.0(8) . . ?
C1 N1 C4 133.1(8) . . ?
C2 N1 C4 115.9(8) . . ?
C3 N2 C1 110.6(9) . . ?
C3 N2 C16 116.3(8) . . ?
C1 N2 C16 133.1(9) . . ?
N1 C1 N2 102.8(8) . . ?
N1 C1 Ta1 129.8(7) . . ?
N2 C1 Ta1 127.4(7) . . ?
C3 C2 N1 106.8(10) . . ?
C3 C2 H2 126.6 . . ?
N1 C2 H2 126.6 . . ?
C2 C3 N2 108.8(10) . . ?
C2 C3 H3 125.6 . . ?
N2 C3 H3 125.6 . . ?
C9 C4 C5 123.0(10) . . ?
C9 C4 N1 118.4(9) . . ?
C5 C4 N1 118.0(9) . . ?
C6 C5 C4 116.8(11) . . ?
C6 C5 C10 121.6(11) . . ?
C4 C5 C10 121.5(9) . . ?
C7 C6 C5 119.9(12) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C8 C7 C6 121.6(11) . . ?
C8 C7 H7 119.2 . . ?
C6 C7 H7 119.2 . . ?
C7 C8 C9 121.6(11) . . ?
C7 C8 H8 119.2 . . ?
C9 C8 H8 119.2 . . ?
C8 C9 C4 116.9(11) . . ?
C8 C9 C13 121.0(10) . . ?
C4 C9 C13 122.1(10) . . ?
C12 C10 C5 111.4(10) . . ?
C12 C10 C11 111.6(9) . . ?
C5 C10 C11 111.2(9) . . ?
C12 C10 H10 107.5 . . ?
C5 C10 H10 107.5 . . ?
C11 C10 H10 107.5 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C9 C13 C14 112.4(11) . . ?
C9 C13 C15 110.3(10) . . ?
C14 C13 C15 110.5(10) . . ?
C9 C13 H13 107.8 . . ?
C14 C13 H13 107.8 . . ?
C15 C13 H13 107.8 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C21 125.0(10) . . ?
C17 C16 N2 118.3(9) . . ?
C21 C16 N2 116.5(9) . . ?
C16 C17 C18 115.6(10) . . ?
C16 C17 C22 123.3(10) . . ?
C18 C17 C22 121.1(10) . . ?
C17 C18 C19 120.9(11) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 H18 119.5 . . ?
C20 C19 C18 120.6(11) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C21 C20 C19 120.6(11) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C20 C21 C16 117.1(11) . . ?
C20 C21 C25 119.6(10) . . ?
C16 C21 C25 123.2(10) . . ?
C17 C22 C24 112.1(11) . . ?
C17 C22 C23 109.6(10) . . ?
C24 C22 C23 111.1(10) . . ?
C17 C22 H22 108.0 . . ?
C24 C22 H22 108.0 . . ?
C23 C22 H22 108.0 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C26 C25 C21 113.7(11) . . ?
C26 C25 C27 109.8(11) . . ?
C21 C25 C27 109.6(10) . . ?
C26 C25 H25 107.9 . . ?
C21 C25 H25 107.9 . . ?
C27 C25 H25 107.9 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N1 C1 N2 0.4(10) . . . . ?
C4 N1 C1 N2 178.1(9) . . . . ?
C2 N1 C1 Ta1 179.4(7) . . . . ?
C4 N1 C1 Ta1 -2.8(15) . . . . ?
C3 N2 C1 N1 -0.7(10) . . . . ?
C16 N2 C1 N1 -177.2(9) . . . . ?
C3 N2 C1 Ta1 -179.8(7) . . . . ?
C16 N2 C1 Ta1 3.8(14) . . . . ?
Br2 Ta1 C1 N1 -175.2(8) . . . . ?
Br4 Ta1 C1 N1 3.6(8) . . . . ?
Br5 Ta1 C1 N1 -86.2(8) . . . . ?
Br3 Ta1 C1 N1 94.2(8) . . . . ?
Br1 Ta1 C1 N1 108(5) . . . . ?
Br2 Ta1 C1 N2 3.5(8) . . . . ?
Br4 Ta1 C1 N2 -177.6(7) . . . . ?
Br5 Ta1 C1 N2 92.6(8) . . . . ?
Br3 Ta1 C1 N2 -87.0(7) . . . . ?
Br1 Ta1 C1 N2 -74(6) . . . . ?
C1 N1 C2 C3 0.0(12) . . . . ?
C4 N1 C2 C3 -178.1(9) . . . . ?
N1 C2 C3 N2 -0.5(13) . . . . ?
C1 N2 C3 C2 0.8(12) . . . . ?
C16 N2 C3 C2 177.9(9) . . . . ?
C1 N1 C4 C9 -92.8(12) . . . . ?
C2 N1 C4 C9 84.8(11) . . . . ?
C1 N1 C4 C5 95.6(13) . . . . ?
C2 N1 C4 C5 -86.8(11) . . . . ?
C9 C4 C5 C6 -1.2(15) . . . . ?
N1 C4 C5 C6 170.0(9) . . . . ?
C9 C4 C5 C10 -178.9(9) . . . . ?
N1 C4 C5 C10 -7.7(14) . . . . ?
C4 C5 C6 C7 1.8(15) . . . . ?
C10 C5 C6 C7 179.5(10) . . . . ?
C5 C6 C7 C8 -1.3(17) . . . . ?
C6 C7 C8 C9 -0.1(18) . . . . ?
C7 C8 C9 C4 0.7(16) . . . . ?
C7 C8 C9 C13 -179.3(10) . . . . ?
C5 C4 C9 C8 -0.1(15) . . . . ?
N1 C4 C9 C8 -171.2(9) . . . . ?
C5 C4 C9 C13 -180.0(9) . . . . ?
N1 C4 C9 C13 8.8(14) . . . . ?
C6 C5 C10 C12 46.3(14) . . . . ?
C4 C5 C10 C12 -136.1(10) . . . . ?
C6 C5 C10 C11 -78.8(13) . . . . ?
C4 C5 C10 C11 98.8(12) . . . . ?
C8 C9 C13 C14 -51.1(14) . . . . ?
C4 C9 C13 C14 128.9(11) . . . . ?
C8 C9 C13 C15 72.7(14) . . . . ?
C4 C9 C13 C15 -107.4(12) . . . . ?
C3 N2 C16 C17 91.3(11) . . . . ?
C1 N2 C16 C17 -92.4(13) . . . . ?
C3 N2 C16 C21 -83.8(12) . . . . ?
C1 N2 C16 C21 92.5(12) . . . . ?
C21 C16 C17 C18 -1.6(16) . . . . ?
N2 C16 C17 C18 -176.3(9) . . . . ?
C21 C16 C17 C22 177.4(10) . . . . ?
N2 C16 C17 C22 2.8(15) . . . . ?
C16 C17 C18 C19 0.9(16) . . . . ?
C22 C17 C18 C19 -178.2(10) . . . . ?
C17 C18 C19 C20 0.0(17) . . . . ?
C18 C19 C20 C21 -0.3(18) . . . . ?
C19 C20 C21 C16 -0.4(16) . . . . ?
C19 C20 C21 C25 177.1(10) . . . . ?
C17 C16 C21 C20 1.4(16) . . . . ?
N2 C16 C21 C20 176.2(9) . . . . ?
C17 C16 C21 C25 -176.0(10) . . . . ?
N2 C16 C21 C25 -1.2(15) . . . . ?
C16 C17 C22 C24 134.4(11) . . . . ?
C18 C17 C22 C24 -46.6(14) . . . . ?
C16 C17 C22 C23 -101.7(13) . . . . ?
C18 C17 C22 C23 77.3(14) . . . . ?
C20 C21 C25 C26 43.2(15) . . . . ?
C16 C21 C25 C26 -139.5(11) . . . . ?
C20 C21 C25 C27 -80.1(14) . . . . ?
C16 C21 C25 C27 97.2(13) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         4.113
_refine_diff_density_min         -1.987
_refine_diff_density_rms         0.239
####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 1437954'
_audit_update_record             
;
2015-11-20 deposited with the CCDC.
2016-03-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H21 F6 N2 Ta'
_chemical_formula_weight         572.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ta Ta -0.7052 6.5227 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pnma

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

_cell_length_a                   11.105(2)
_cell_length_b                   16.481(3)
_cell_length_c                   10.701(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1958.7(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5125
_cell_measurement_theta_min      2.4715
_cell_measurement_theta_max      27.0765

_exptl_crystal_description       needle
_exptl_crystal_colour            pale-yellow
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.941
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1104
_exptl_absorpt_coefficient_mu    5.673
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.4638
_exptl_absorpt_correction_T_max  0.6008
_exptl_absorpt_process_details   
; 
 Data were corrected for Lorentz polarization and absorption
 effects (empirical absorption correction SADABS).
 R(int) =  0.1516 (selected reflections only, before parameter refinement)
 R(int) =  0.0674 (selected reflections only, after parameter refinement)
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17842
_diffrn_reflns_av_R_equivalents  0.0609
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.27
_diffrn_reflns_theta_max         27.00
_reflns_number_total             2220
_reflns_number_gt                1876
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1996)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0211P)²+2.8778P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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         2220
_refine_ls_number_parameters     135
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0348
_refine_ls_R_factor_gt           0.0238
_refine_ls_wR_factor_ref         0.0549
_refine_ls_wR_factor_gt          0.0499
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ta1 Ta 0.904389(19) 0.7500 0.02101(2) 0.01719(8) Uani 1 2 d S . .
F1 F 1.0676(3) 0.7500 -0.0331(3) 0.0282(7) Uani 1 2 d S . .
F2 F 0.8697(2) 0.66990(14) -0.1003(2) 0.0293(5) Uani 1 1 d . . .
F3 F 0.9395(2) 0.66840(13) 0.1404(2) 0.0266(5) Uani 1 1 d . . .
F4 F 0.7415(3) 0.7500 0.0740(3) 0.0293(7) Uani 1 2 d S . .
N1 N 0.3650(3) 0.68421(18) 0.9539(3) 0.0192(7) Uani 1 1 d . . .
C1 C 0.3742(3) 0.7090(2) 1.0768(3) 0.0217(8) Uani 1 1 d . . .
H1 H 0.3795 0.6748 1.1481 0.026 Uiso 1 1 calc R . .
C2 C 0.3591(5) 0.7500 0.8817(5) 0.0172(11) Uani 1 2 d S . .
H2 H 0.3519 0.7500 0.7933 0.021 Uiso 1 2 calc SR . .
C3 C 0.3744(3) 0.6007(2) 0.9107(3) 0.0184(8) Uani 1 1 d . . .
C4 C 0.4817(3) 0.5776(2) 0.8518(3) 0.0197(8) Uani 1 1 d . . .
C5 C 0.4902(3) 0.4974(2) 0.8117(4) 0.0218(8) Uani 1 1 d . . .
H5 H 0.5606 0.4796 0.7695 0.026 Uiso 1 1 calc R . .
C6 C 0.3967(3) 0.4431(2) 0.8328(3) 0.0226(8) Uani 1 1 d . . .
H6 H 0.4040 0.3886 0.8048 0.027 Uiso 1 1 calc R . .
C7 C 0.2937(4) 0.4673(2) 0.8939(3) 0.0225(8) Uani 1 1 d . . .
H7 H 0.2311 0.4290 0.9082 0.027 Uiso 1 1 calc R . .
C8 C 0.2796(3) 0.5471(2) 0.9353(3) 0.0210(8) Uani 1 1 d . . .
C9 C 0.5851(3) 0.6352(2) 0.8328(4) 0.0249(8) Uani 1 1 d . . .
H9A H 0.6584 0.6042 0.8145 0.037 Uiso 1 1 calc R . .
H9B H 0.5972 0.6673 0.9088 0.037 Uiso 1 1 calc R . .
H9C H 0.5672 0.6715 0.7627 0.037 Uiso 1 1 calc R . .
C10 C 0.1656(4) 0.5710(2) 1.0012(4) 0.0272(9) Uani 1 1 d . . .
H10A H 0.1798 0.6203 1.0502 0.041 Uiso 1 1 calc R . .
H10B H 0.1404 0.5270 1.0570 0.041 Uiso 1 1 calc R . .
H10C H 0.1023 0.5812 0.9394 0.041 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ta1 F2 1.891(2) . ?
Ta1 F2 1.891(2) 7_575 ?
Ta1 F4 1.895(3) . ?
Ta1 F3 1.896(2) 7_575 ?
Ta1 F3 1.896(2) . ?
Ta1 F1 1.902(3) . ?
N1 C2 1.332(4) . ?
N1 C1 1.382(5) . ?
N1 C3 1.456(4) . ?
C1 C1 1.351(7) 7_575 ?
C1 H1 0.9500 . ?
C2 N1 1.332(4) 7_575 ?
C2 H2 0.9500 . ?
C3 C8 1.399(5) . ?
C3 C4 1.400(5) . ?
C4 C5 1.394(5) . ?
C4 C9 1.503(5) . ?
C5 C6 1.388(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.377(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.397(5) . ?
C7 H7 0.9500 . ?
C8 C10 1.501(5) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F2 Ta1 F2 88.56(14) . 7_575 ?
F2 Ta1 F4 90.63(10) . . ?
F2 Ta1 F4 90.63(10) 7_575 . ?
F2 Ta1 F3 179.03(9) . 7_575 ?
F2 Ta1 F3 90.52(10) 7_575 7_575 ?
F4 Ta1 F3 89.68(10) . 7_575 ?
F2 Ta1 F3 90.52(10) . . ?
F2 Ta1 F3 179.03(9) 7_575 . ?
F4 Ta1 F3 89.68(10) . . ?
F3 Ta1 F3 90.39(14) 7_575 . ?
F2 Ta1 F1 89.16(10) . . ?
F2 Ta1 F1 89.16(10) 7_575 . ?
F4 Ta1 F1 179.71(14) . . ?
F3 Ta1 F1 90.53(10) 7_575 . ?
F3 Ta1 F1 90.53(10) . . ?
C2 N1 C1 108.3(3) . . ?
C2 N1 C3 126.1(3) . . ?
C1 N1 C3 125.2(3) . . ?
C1 C1 N1 107.21(19) 7_575 . ?
C1 C1 H1 126.4 7_575 . ?
N1 C1 H1 126.4 . . ?
N1 C2 N1 108.9(4) 7_575 . ?
N1 C2 H2 125.5 7_575 . ?
N1 C2 H2 125.5 . . ?
C8 C3 C4 123.6(3) . . ?
C8 C3 N1 118.9(3) . . ?
C4 C3 N1 117.5(3) . . ?
C5 C4 C3 117.0(3) . . ?
C5 C4 C9 120.4(3) . . ?
C3 C4 C9 122.6(3) . . ?
C6 C5 C4 120.7(4) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C7 C6 C5 120.8(3) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C7 C8 121.0(4) . . ?
C6 C7 H7 119.5 . . ?
C8 C7 H7 119.5 . . ?
C7 C8 C3 116.8(3) . . ?
C7 C8 C10 119.3(3) . . ?
C3 C8 C10 123.9(3) . . ?
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 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N1 C1 C1 -0.2(3) . . . 7_575 ?
C3 N1 C1 C1 173.2(3) . . . 7_575 ?
C1 N1 C2 N1 0.4(6) . . . 7_575 ?
C3 N1 C2 N1 -173.0(2) . . . 7_575 ?
C2 N1 C3 C8 -115.2(4) . . . . ?
C1 N1 C3 C8 72.5(5) . . . . ?
C2 N1 C3 C4 68.0(5) . . . . ?
C1 N1 C3 C4 -104.4(4) . . . . ?
C8 C3 C4 C5 2.8(5) . . . . ?
N1 C3 C4 C5 179.5(3) . . . . ?
C8 C3 C4 C9 -176.5(4) . . . . ?
N1 C3 C4 C9 0.2(5) . . . . ?
C3 C4 C5 C6 -1.6(5) . . . . ?
C9 C4 C5 C6 177.7(3) . . . . ?
C4 C5 C6 C7 0.0(6) . . . . ?
C5 C6 C7 C8 0.6(6) . . . . ?
C6 C7 C8 C3 0.5(5) . . . . ?
C6 C7 C8 C10 179.9(3) . . . . ?
C4 C3 C8 C7 -2.3(5) . . . . ?
N1 C3 C8 C7 -178.9(3) . . . . ?
C4 C3 C8 C10 178.4(3) . . . . ?
N1 C3 C8 C10 1.8(5) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         1.084
_refine_diff_density_min         -0.925
_refine_diff_density_rms         0.127

