# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_p2121

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_absolute_configuration ad
_chemical_formula_sum            'C5 H9 Cl7 N Nb O'
_chemical_formula_weight         440.19

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Nb Nb -2.0727 0.6215 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

loop_
_symmetry_equiv_pos_as_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                   6.658(2)
_cell_length_b                   13.408(4)
_cell_length_c                   15.881(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1417.8(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5835
_cell_measurement_theta_min      2.565
_cell_measurement_theta_max      28.262

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.062
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             856
_exptl_absorpt_coefficient_mu    2.142
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.6165
_exptl_absorpt_correction_T_max  0.7256
_exptl_absorpt_process_details   
;
 Data were corrected for Lorentz polarization and absorption
 effects (empirical absorption corrections SADABS).
 R(int) = 0.1429 (selected reflections only, before parameter refinement)
 R(int) = 0.0601 (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            11785
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.99
_diffrn_reflns_theta_max         27.10
_reflns_number_total             3124
_reflns_number_gt                2969
_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. The following restraints
 were applied (given as SHELXL lines):  
 DFIX 0.92 0.02 H1A N1  N1 H1B
;

_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)+(0.0158P)²+0.2709P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.11(5)
_refine_ls_number_reflns         3124
_refine_ls_number_parameters     142
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0259
_refine_ls_R_factor_gt           0.0238
_refine_ls_wR_factor_ref         0.0502
_refine_ls_wR_factor_gt          0.0492
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3517(5) 0.7824(2) 0.27672(19) 0.0231(7) Uani 1 1 d . . .
C2 C 0.5793(5) 0.7843(2) 0.28038(17) 0.0228(7) Uani 1 1 d . . .
H2 H 0.6288 0.8545 0.2851 0.027 Uiso 1 1 calc R . .
C3 C 0.6816(5) 0.7311(3) 0.2065(2) 0.0326(9) Uani 1 1 d . . .
H3A H 0.5985 0.7353 0.1549 0.039 Uiso 1 1 calc R . .
H3B H 0.8153 0.7603 0.1948 0.039 Uiso 1 1 calc R . .
C4 C 0.7003(6) 0.6241(3) 0.2361(2) 0.0332(8) Uani 1 1 d . . .
H4A H 0.5707 0.5884 0.2312 0.040 Uiso 1 1 calc R . .
H4B H 0.8038 0.5878 0.2036 0.040 Uiso 1 1 calc R . .
C5 C 0.7620(5) 0.6353(3) 0.32748(19) 0.0281(8) Uani 1 1 d . . .
H5A H 0.7267 0.5751 0.3604 0.034 Uiso 1 1 calc R . .
H5B H 0.9081 0.6476 0.3325 0.034 Uiso 1 1 calc R . .
Cl1 Cl 0.25505(15) 0.85371(8) 0.19373(6) 0.0444(3) Uani 1 1 d . . .
N1 N 0.6430(4) 0.7243(2) 0.35648(17) 0.0263(6) Uani 1 1 d D . .
H1A H 0.721(4) 0.765(2) 0.3900(18) 0.032 Uiso 1 1 d D . .
H1B H 0.537(4) 0.702(2) 0.3864(19) 0.032 Uiso 1 1 d D . .
O1 O 0.2455(4) 0.73854(16) 0.32353(14) 0.0295(5) Uani 1 1 d . . .
Nb1 Nb 0.78698(4) 1.014324(18) 0.478936(16) 0.01344(7) Uani 1 1 d . . .
Cl2 Cl 0.96075(11) 0.85427(5) 0.46580(5) 0.02044(16) Uani 1 1 d . . .
Cl3 Cl 1.09961(10) 1.08842(5) 0.48791(5) 0.02118(16) Uani 1 1 d . . .
Cl4 Cl 0.77921(13) 0.99187(5) 0.62458(4) 0.02482(16) Uani 1 1 d . . .
Cl5 Cl 0.61048(12) 1.16061(5) 0.49120(5) 0.02618(18) Uani 1 1 d . . .
Cl6 Cl 0.48757(11) 0.92033(5) 0.46323(5) 0.02083(16) Uani 1 1 d . . .
Cl7 Cl 0.80384(12) 1.02915(6) 0.33140(4) 0.02661(18) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0312(19) 0.0155(16) 0.0227(16) -0.0055(14) 0.0026(14) -0.0015(14)
C2 0.0307(19) 0.0240(17) 0.0136(15) 0.0007(13) 0.0014(13) -0.0108(15)
C3 0.0268(19) 0.055(2) 0.0163(15) -0.0037(16) 0.0053(15) -0.0117(18)
C4 0.0206(18) 0.049(2) 0.0301(18) -0.0198(16) 0.0042(15) -0.0043(18)
C5 0.0162(16) 0.038(2) 0.0296(17) -0.0031(15) -0.0006(14) -0.0014(14)
Cl1 0.0424(6) 0.0494(6) 0.0413(5) 0.0190(4) -0.0053(5) -0.0057(5)
N1 0.0347(16) 0.0258(16) 0.0184(14) -0.0027(12) 0.0005(12) -0.0085(13)
O1 0.0332(14) 0.0229(12) 0.0325(12) -0.0012(10) 0.0126(11) -0.0054(11)
Nb1 0.01434(12) 0.01356(11) 0.01243(11) 0.00030(10) -0.00053(10) -0.00065(10)
Cl2 0.0200(4) 0.0166(3) 0.0248(4) -0.0042(3) -0.0032(3) 0.0030(3)
Cl3 0.0168(3) 0.0208(4) 0.0259(4) -0.0023(3) -0.0014(3) -0.0039(3)
Cl4 0.0350(4) 0.0261(4) 0.0133(3) 0.0006(3) 0.0015(3) -0.0025(4)
Cl5 0.0242(4) 0.0165(4) 0.0379(5) -0.0012(3) -0.0034(3) 0.0036(3)
Cl6 0.0149(3) 0.0192(4) 0.0284(4) -0.0044(3) 0.0017(3) -0.0026(3)
Cl7 0.0277(4) 0.0384(4) 0.0137(3) 0.0043(3) -0.0018(3) -0.0077(4)

_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 O1 1.183(4) . ?
C1 C2 1.516(5) . ?
C1 Cl1 1.751(3) . ?
C2 N1 1.512(4) . ?
C2 C3 1.534(4) . ?
C2 H2 1.0000 . ?
C3 C4 1.515(5) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.515(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 N1 1.505(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
N1 H1A 0.924(18) . ?
N1 H1B 0.903(18) . ?
Nb1 Cl5 2.2948(9) . ?
Nb1 Cl3 2.3110(9) . ?
Nb1 Cl4 2.3330(10) . ?
Nb1 Cl7 2.3541(10) . ?
Nb1 Cl6 2.3716(9) . ?
Nb1 Cl2 2.4470(9) . ?

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
O1 C1 C2 125.6(3) . . ?
O1 C1 Cl1 121.7(3) . . ?
C2 C1 Cl1 112.8(2) . . ?
N1 C2 C1 107.6(3) . . ?
N1 C2 C3 103.9(3) . . ?
C1 C2 C3 114.0(3) . . ?
N1 C2 H2 110.4 . . ?
C1 C2 H2 110.4 . . ?
C3 C2 H2 110.4 . . ?
C4 C3 C2 103.8(3) . . ?
C4 C3 H3A 111.0 . . ?
C2 C3 H3A 111.0 . . ?
C4 C3 H3B 111.0 . . ?
C2 C3 H3B 111.0 . . ?
H3A C3 H3B 109.0 . . ?
C5 C4 C3 103.1(3) . . ?
C5 C4 H4A 111.1 . . ?
C3 C4 H4A 111.1 . . ?
C5 C4 H4B 111.1 . . ?
C3 C4 H4B 111.1 . . ?
H4A C4 H4B 109.1 . . ?
N1 C5 C4 103.2(3) . . ?
N1 C5 H5A 111.1 . . ?
C4 C5 H5A 111.1 . . ?
N1 C5 H5B 111.1 . . ?
C4 C5 H5B 111.1 . . ?
H5A C5 H5B 109.1 . . ?
C5 N1 C2 109.0(2) . . ?
C5 N1 H1A 111(2) . . ?
C2 N1 H1A 107(2) . . ?
C5 N1 H1B 108(2) . . ?
C2 N1 H1B 112(2) . . ?
H1A N1 H1B 110(3) . . ?
Cl5 Nb1 Cl3 95.08(4) . . ?
Cl5 Nb1 Cl4 90.85(3) . . ?
Cl3 Nb1 Cl4 90.82(3) . . ?
Cl5 Nb1 Cl7 92.10(3) . . ?
Cl3 Nb1 Cl7 88.98(3) . . ?
Cl4 Nb1 Cl7 177.05(3) . . ?
Cl5 Nb1 Cl6 91.87(4) . . ?
Cl3 Nb1 Cl6 172.79(3) . . ?
Cl4 Nb1 Cl6 90.98(3) . . ?
Cl7 Nb1 Cl6 88.87(3) . . ?
Cl5 Nb1 Cl2 177.41(3) . . ?
Cl3 Nb1 Cl2 87.50(3) . . ?
Cl4 Nb1 Cl2 88.96(3) . . ?
Cl7 Nb1 Cl2 88.09(3) . . ?
Cl6 Nb1 Cl2 85.55(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 N1 -2.6(4) . . . . ?
Cl1 C1 C2 N1 177.5(2) . . . . ?
O1 C1 C2 C3 112.0(4) . . . . ?
Cl1 C1 C2 C3 -67.9(3) . . . . ?
N1 C2 C3 C4 28.0(3) . . . . ?
C1 C2 C3 C4 -88.8(3) . . . . ?
C2 C3 C4 C5 -41.1(3) . . . . ?
C3 C4 C5 N1 37.6(3) . . . . ?
C4 C5 N1 C2 -20.4(3) . . . . ?
C1 C2 N1 C5 116.5(3) . . . . ?
C3 C2 N1 C5 -4.6(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A Cl2 0.924(18) 2.329(19) 3.244(3) 171(3) .
N1 H1A Cl6 0.924(18) 2.84(3) 3.294(3) 111(2) .
N1 H1B O1 0.903(18) 2.24(3) 2.704(4) 112(3) .
N1 H1B Cl2 0.903(18) 2.52(3) 3.248(3) 139(3) 4_466

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        27.10
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.502
_refine_diff_density_min         -0.487
_refine_diff_density_rms         0.081
_database_code_depnum_ccdc_archive 'CCDC 1009695'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_p2121

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_absolute_configuration ad
_chemical_formula_sum            'C5 H9 Cl7 N O Ta'
_chemical_formula_weight         528.23

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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   P2(1)2(1)2(1)

loop_
_symmetry_equiv_pos_as_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                   7.7230(13)
_cell_length_b                   11.633(2)
_cell_length_c                   15.913(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1429.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9902
_cell_measurement_theta_min      2.560
_cell_measurement_theta_max      28.700

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.454
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             984
_exptl_absorpt_coefficient_mu    8.970
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.2429
_exptl_absorpt_correction_T_max  0.3464
_exptl_absorpt_process_details   
;
 Data were corrected for Lorentz polarization and absorption
 effects (empirical absorption corrections SADABS).
 R(int) = 0.1624 (selected reflections only, before parameter refinement)
 R(int) = 0.0769 (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            14819
_diffrn_reflns_av_R_equivalents  0.0448
_diffrn_reflns_av_unetI/netI     0.0396
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.56
_diffrn_reflns_theta_max         26.99
_reflns_number_total             3105
_reflns_number_gt                3052
_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. The following restraints
 were applied (given as SHELXL lines):  
 simu $c
;

_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)+(0.0199P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.024(7)
_refine_ls_number_reflns         3105
_refine_ls_number_parameters     136
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.0243
_refine_ls_R_factor_gt           0.0236
_refine_ls_wR_factor_ref         0.0527
_refine_ls_wR_factor_gt          0.0523
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.050
_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 0.21508(2) 0.490352(17) 0.030834(11) 0.01360(6) Uani 1 1 d . . .
Cl6 Cl 0.14653(15) 0.48435(12) 0.17447(7) 0.0200(3) Uani 1 1 d . . .
Cl2 Cl -0.07335(16) 0.52201(12) -0.00425(8) 0.0251(3) Uani 1 1 d . . .
Cl4 Cl 0.18345(18) 0.29478(11) 0.01742(8) 0.0251(3) Uani 1 1 d . . .
Cl3 Cl 0.30144(16) 0.50743(12) -0.10974(7) 0.0262(3) Uani 1 1 d . . .
Cl5 Cl 0.51110(15) 0.47066(12) 0.06982(8) 0.0216(3) Uani 1 1 d . . .
Cl7 Cl 0.24923(15) 0.69559(10) 0.04398(7) 0.0202(3) Uani 1 1 d . . .
C1 C 0.6069(7) 0.3051(5) 0.2670(3) 0.0198(12) Uani 1 1 d U . .
C2 C 0.4998(7) 0.1995(5) 0.2773(3) 0.0169(11) Uani 1 1 d U . .
H2 H 0.5743 0.1316 0.2905 0.020 Uiso 1 1 calc R . .
C3 C 0.3875(7) 0.1763(5) 0.2001(3) 0.0190(12) Uani 1 1 d U . .
H3A H 0.4402 0.1164 0.1641 0.023 Uiso 1 1 calc R . .
H3B H 0.3718 0.2472 0.1665 0.023 Uiso 1 1 calc R . .
C4 C 0.2144(8) 0.1352(6) 0.2361(4) 0.0356(14) Uani 1 1 d U . .
H4A H 0.1197 0.1474 0.1952 0.043 Uiso 1 1 calc R . .
H4B H 0.2198 0.0524 0.2504 0.043 Uiso 1 1 calc R . .
C5 C 0.1863(8) 0.2057(6) 0.3129(4) 0.0309(15) Uani 1 1 d U . .
H5A H 0.1115 0.1651 0.3538 0.037 Uiso 1 1 calc R . .
H5B H 0.1332 0.2808 0.2989 0.037 Uiso 1 1 calc R . .
Cl1 Cl 0.7845(2) 0.28322(12) 0.20036(9) 0.0274(3) Uani 1 1 d . . .
N1 N 0.3702(6) 0.2211(4) 0.3473(3) 0.0225(10) Uani 1 1 d . . .
H1A H 0.3837 0.2945 0.3679 0.027 Uiso 1 1 calc R . .
H1B H 0.3891 0.1702 0.3906 0.027 Uiso 1 1 calc R . .
O1 O 0.5772(6) 0.3954(3) 0.2975(3) 0.0355(11) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Ta1 0.01679(10) 0.01242(10) 0.01158(9) -0.00069(8) -0.00109(7) 0.00086(8)
Cl6 0.0244(6) 0.0220(7) 0.0137(5) 0.0006(5) 0.0026(4) -0.0022(6)
Cl2 0.0198(6) 0.0299(8) 0.0255(6) -0.0041(6) -0.0059(5) 0.0025(6)
Cl4 0.0362(7) 0.0148(6) 0.0242(7) -0.0025(5) -0.0079(6) -0.0020(5)
Cl3 0.0352(7) 0.0289(7) 0.0146(5) 0.0000(6) 0.0044(5) 0.0042(8)
Cl5 0.0172(5) 0.0223(7) 0.0255(6) -0.0040(5) -0.0017(5) 0.0040(5)
Cl7 0.0271(7) 0.0143(6) 0.0191(6) 0.0001(5) -0.0032(5) 0.0003(4)
C1 0.018(3) 0.025(3) 0.017(3) -0.002(2) 0.000(2) -0.003(2)
C2 0.021(2) 0.011(3) 0.018(3) 0.003(2) 0.002(2) 0.000(2)
C3 0.021(3) 0.018(3) 0.018(3) -0.006(2) -0.002(2) -0.003(2)
C4 0.020(3) 0.038(4) 0.049(4) -0.015(3) -0.005(3) 0.006(3)
C5 0.022(3) 0.041(4) 0.030(3) -0.003(3) 0.004(3) -0.003(3)
Cl1 0.0200(6) 0.0300(7) 0.0321(7) 0.0005(6) 0.0041(6) -0.0013(7)
N1 0.028(3) 0.023(3) 0.016(2) 0.004(2) 0.0018(18) 0.002(2)
O1 0.046(3) 0.017(2) 0.043(3) -0.016(2) 0.014(2) -0.009(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
Ta1 Cl4 2.2981(13) . ?
Ta1 Cl2 2.3258(12) . ?
Ta1 Cl3 2.3427(12) . ?
Ta1 Cl6 2.3472(11) . ?
Ta1 Cl5 2.3800(12) . ?
Ta1 Cl7 2.4112(13) . ?
C1 O1 1.180(7) . ?
C1 C2 1.489(8) . ?
C1 Cl1 1.752(5) . ?
C2 N1 1.519(6) . ?
C2 C3 1.528(7) . ?
C2 H2 1.0000 . ?
C3 C4 1.531(8) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.488(8) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 N1 1.533(7) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
N1 H1A 0.9200 . ?
N1 H1B 0.9200 . ?

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
Cl4 Ta1 Cl2 91.87(5) . . ?
Cl4 Ta1 Cl3 91.46(5) . . ?
Cl2 Ta1 Cl3 91.72(4) . . ?
Cl4 Ta1 Cl6 92.12(5) . . ?
Cl2 Ta1 Cl6 91.28(4) . . ?
Cl3 Ta1 Cl6 175.24(5) . . ?
Cl4 Ta1 Cl5 91.78(5) . . ?
Cl2 Ta1 Cl5 176.25(5) . . ?
Cl3 Ta1 Cl5 89.06(4) . . ?
Cl6 Ta1 Cl5 87.70(4) . . ?
Cl4 Ta1 Cl7 179.61(4) . . ?
Cl2 Ta1 Cl7 88.21(5) . . ?
Cl3 Ta1 Cl7 88.15(4) . . ?
Cl6 Ta1 Cl7 88.26(4) . . ?
Cl5 Ta1 Cl7 88.14(4) . . ?
O1 C1 C2 125.5(5) . . ?
O1 C1 Cl1 122.0(5) . . ?
C2 C1 Cl1 112.5(4) . . ?
C1 C2 N1 108.1(4) . . ?
C1 C2 C3 111.8(4) . . ?
N1 C2 C3 104.2(4) . . ?
C1 C2 H2 110.8 . . ?
N1 C2 H2 110.8 . . ?
C3 C2 H2 110.8 . . ?
C2 C3 C4 104.4(4) . . ?
C2 C3 H3A 110.9 . . ?
C4 C3 H3A 110.9 . . ?
C2 C3 H3B 110.9 . . ?
C4 C3 H3B 110.9 . . ?
H3A C3 H3B 108.9 . . ?
C5 C4 C3 105.2(5) . . ?
C5 C4 H4A 110.7 . . ?
C3 C4 H4A 110.7 . . ?
C5 C4 H4B 110.7 . . ?
C3 C4 H4B 110.7 . . ?
H4A C4 H4B 108.8 . . ?
C4 C5 N1 102.8(4) . . ?
C4 C5 H5A 111.2 . . ?
N1 C5 H5A 111.2 . . ?
C4 C5 H5B 111.2 . . ?
N1 C5 H5B 111.2 . . ?
H5A C5 H5B 109.1 . . ?
C2 N1 C5 109.2(4) . . ?
C2 N1 H1A 109.8 . . ?
C5 N1 H1A 109.8 . . ?
C2 N1 H1B 109.8 . . ?
C5 N1 H1B 109.8 . . ?
H1A N1 H1B 108.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 N1 -11.8(7) . . . . ?
Cl1 C1 C2 N1 170.0(3) . . . . ?
O1 C1 C2 C3 102.4(6) . . . . ?
Cl1 C1 C2 C3 -75.8(5) . . . . ?
C1 C2 C3 C4 -140.2(5) . . . . ?
N1 C2 C3 C4 -23.7(5) . . . . ?
C2 C3 C4 C5 37.6(6) . . . . ?
C3 C4 C5 N1 -35.1(6) . . . . ?
C1 C2 N1 C5 121.5(5) . . . . ?
C3 C2 N1 C5 2.4(6) . . . . ?
C4 C5 N1 C2 20.4(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O1 0.92 2.21 2.701(6) 113.0 .
N1 H1B Cl5 0.92 2.53 3.326(5) 145.7 3_645

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.99
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         1.254
_refine_diff_density_min         -1.722
_refine_diff_density_rms         0.171
_database_code_depnum_ccdc_archive 'CCDC 1009696'
