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

data_p
_database_code_depnum_ccdc_archive 'CCDC 1851694'
_audit_update_record             
;
2018-06-26 deposited with the CCDC.
2018-08-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H24 Cl2 N O2 Ta'
_chemical_formula_weight         598.28

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_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+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   16.8270(12)
_cell_length_b                   14.9556(10)
_cell_length_c                   8.5588(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2153.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    140(2)
_cell_measurement_reflns_used    6108
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      24.88

_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.845
_exptl_crystal_F_000             1168
_exptl_transmission_factor_min   0.445
_exptl_transmission_factor_max   0.565
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    5.371
_shelx_estimated_absorpt_T_min   0.445
_shelx_estimated_absorpt_T_max   0.565
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'SADABS 2014/5'

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      140(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23448
_diffrn_reflns_av_unetI/netI     0.0691
_diffrn_reflns_av_R_equivalents  0.1107
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.421
_diffrn_reflns_theta_max         24.994
_diffrn_reflns_theta_full        24.994
_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 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3784
_reflns_number_gt                3181
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.859
_reflns_Friedel_fraction_max     0.993
_reflns_Friedel_fraction_full    0.993

_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       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0652P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1265 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.021(15)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3784
_refine_ls_number_parameters     267
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0475
_refine_ls_wR_factor_ref         0.1103
_refine_ls_wR_factor_gt          0.1055
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.000
_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
Ta Ta 0.17444(3) 0.23815(3) 0.75095(13) 0.01598(19) Uani 1 1 d . . . . .
N1 N 0.0795(8) 0.2776(11) 0.9273(18) 0.021(4) Uani 1 1 d . . . . .
C1 C 0.1410(9) 0.4410(9) 0.778(2) 0.020(4) Uani 1 1 d . . . . .
O1 O 0.1787(5) 0.3666(7) 0.7241(14) 0.023(3) Uani 1 1 d . . . . .
O2 O 0.1343(7) 0.1248(7) 0.8405(12) 0.028(3) Uani 1 1 d . . . . .
Cl1 Cl 0.2469(4) 0.2592(4) 0.9940(7) 0.0316(15) Uani 1 1 d . . . . .
Cl2 Cl 0.0517(3) 0.2450(3) 0.6024(6) 0.0332(12) Uani 1 1 d . . . . .
C2 C 0.0834(9) 0.4386(10) 0.8909(18) 0.020(3) Uani 1 1 d . . . . .
C3 C 0.0469(9) 0.5187(12) 0.9409(19) 0.030(4) Uani 1 1 d . . . . .
H3A H 0.0054 0.5166 1.0161 0.037 Uiso 1 1 calc R U . . .
C4 C 0.0714(10) 0.6008(11) 0.881(2) 0.038(5) Uani 1 1 d . . . . .
H4A H 0.0465 0.6548 0.9127 0.046 Uiso 1 1 calc R U . . .
C5 C 0.1326(9) 0.6020(9) 0.774(2) 0.026(4) Uani 1 1 d . . . . .
H5A H 0.1515 0.6577 0.7352 0.032 Uiso 1 1 calc R U . . .
C6 C 0.1668(9) 0.5241(10) 0.7215(19) 0.027(5) Uani 1 1 d . . . . .
H6A H 0.2083 0.5266 0.6464 0.032 Uiso 1 1 calc R U . . .
C7 C 0.0547(10) 0.3544(11) 0.9589(18) 0.025(4) Uani 1 1 d . . . . .
H7A H 0.0133 0.3586 1.0341 0.030 Uiso 1 1 calc R U . . .
C8 C 0.0455(9) 0.2002(10) 1.0022(18) 0.021(3) Uani 1 1 d . . . . .
C9 C 0.0779(9) 0.1212(10) 0.9510(19) 0.022(4) Uani 1 1 d . . . . .
C10 C 0.0507(10) 0.0410(10) 1.0109(17) 0.024(3) Uani 1 1 d . . . . .
H10A H 0.0742 -0.0136 0.9777 0.028 Uiso 1 1 calc R U . . .
C11 C -0.0108(11) 0.0397(11) 1.1200(19) 0.035(4) Uani 1 1 d . . . . .
H11A H -0.0305 -0.0155 1.1591 0.042 Uiso 1 1 calc R U . . .
C12 C -0.0430(10) 0.1200(12) 1.171(2) 0.037(4) Uani 1 1 d . . . . .
H12A H -0.0840 0.1199 1.2472 0.045 Uiso 1 1 calc R U . . .
C13 C -0.0161(11) 0.1994(11) 1.111(2) 0.034(4) Uani 1 1 d . . . . .
H13A H -0.0395 0.2540 1.1442 0.041 Uiso 1 1 calc R U . . .
C15 C 0.3006(12) 0.2578(10) 0.620(2) 0.029(4) Uani 1 1 d . . . . .
C16 C 0.3052(9) 0.1723(11) 0.6925(17) 0.021(3) Uani 1 1 d . . . . .
C17 C 0.2499(8) 0.1166(10) 0.6147(18) 0.020(3) Uani 1 1 d . . . . .
C18 C 0.2099(10) 0.1672(11) 0.4985(17) 0.026(4) Uani 1 1 d . . . . .
C19 C 0.246(2) 0.2560(18) 0.505(4) 0.050(9) Uani 1 1 d . . . . .
C20 C 0.3535(11) 0.3373(12) 0.661(2) 0.048(6) Uani 1 1 d . . . . .
H20A H 0.3675 0.3349 0.7716 0.072 Uiso 1 1 calc R U . . .
H20B H 0.3249 0.3930 0.6388 0.072 Uiso 1 1 calc R U . . .
H20C H 0.4020 0.3351 0.5973 0.072 Uiso 1 1 calc R U . . .
C21 C 0.3677(10) 0.1407(12) 0.8039(18) 0.035(4) Uani 1 1 d . . . . .
H21A H 0.3481 0.0884 0.8611 0.052 Uiso 1 1 calc R U . . .
H21B H 0.3803 0.1887 0.8780 0.052 Uiso 1 1 calc R U . . .
H21C H 0.4157 0.1245 0.7456 0.052 Uiso 1 1 calc R U . . .
C22 C 0.2399(10) 0.0188(10) 0.645(2) 0.038(5) Uani 1 1 d . . . . .
H22A H 0.1980 -0.0050 0.5772 0.057 Uiso 1 1 calc R U . . .
H22B H 0.2253 0.0094 0.7545 0.057 Uiso 1 1 calc R U . . .
H22C H 0.2900 -0.0122 0.6228 0.057 Uiso 1 1 calc R U . . .
C23 C 0.1545(11) 0.1322(15) 0.377(2) 0.049(6) Uani 1 1 d . . . . .
H23A H 0.1164 0.1789 0.3489 0.073 Uiso 1 1 calc R U . . .
H23B H 0.1259 0.0803 0.4190 0.073 Uiso 1 1 calc R U . . .
H23C H 0.1848 0.1143 0.2848 0.073 Uiso 1 1 calc R U . . .
C24 C 0.2200(13) 0.3283(12) 0.394(2) 0.044(5) Uani 1 1 d . . . . .
H24A H 0.1699 0.3108 0.3438 0.066 Uiso 1 1 calc R U . . .
H24B H 0.2609 0.3368 0.3134 0.066 Uiso 1 1 calc R U . . .
H24C H 0.2123 0.3843 0.4511 0.066 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
Ta O1 1.936(10) . ?
Ta O2 1.979(10) . ?
Ta N1 2.276(15) . ?
Ta C15 2.418(19) . ?
Ta Cl2 2.427(5) . ?
Ta Cl1 2.432(6) . ?
Ta C19 2.44(3) . ?
Ta C16 2.462(16) . ?
Ta C18 2.480(15) . ?
Ta C17 2.505(14) . ?
N1 C7 1.25(2) . ?
N1 C8 1.44(2) . ?
C1 O1 1.361(17) . ?
C1 C2 1.37(2) . ?
C1 C6 1.40(2) . ?
O2 C9 1.341(18) . ?
C2 C3 1.41(2) . ?
C2 C7 1.47(2) . ?
C3 C4 1.39(2) . ?
C3 H3A 0.9500 . ?
C4 C5 1.38(2) . ?
C4 H4A 0.9500 . ?
C5 C6 1.37(2) . ?
C5 H5A 0.9500 . ?
C6 H6A 0.9500 . ?
C7 H7A 0.9500 . ?
C8 C9 1.37(2) . ?
C8 C13 1.40(2) . ?
C9 C10 1.38(2) . ?
C10 C11 1.40(2) . ?
C10 H10A 0.9500 . ?
C11 C12 1.39(2) . ?
C11 H11A 0.9500 . ?
C12 C13 1.37(2) . ?
C12 H12A 0.9500 . ?
C13 H13A 0.9500 . ?
C15 C19 1.35(4) . ?
C15 C16 1.42(2) . ?
C15 C20 1.52(2) . ?
C16 C17 1.41(2) . ?
C16 C21 1.50(2) . ?
C17 C18 1.42(2) . ?
C17 C22 1.50(2) . ?
C18 C19 1.46(3) . ?
C18 C23 1.49(2) . ?
C19 C24 1.51(4) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 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
O1 Ta O2 155.3(4) . . ?
O1 Ta N1 81.2(5) . . ?
O2 Ta N1 74.1(5) . . ?
O1 Ta C15 78.0(5) . . ?
O2 Ta C15 125.7(5) . . ?
N1 Ta C15 153.1(6) . . ?
O1 Ta Cl2 85.9(3) . . ?
O2 Ta Cl2 87.0(4) . . ?
N1 Ta Cl2 74.9(4) . . ?
C15 Ta Cl2 119.9(5) . . ?
O1 Ta Cl1 87.4(4) . . ?
O2 Ta Cl1 87.2(4) . . ?
N1 Ta Cl1 75.6(4) . . ?
C15 Ta Cl1 86.6(5) . . ?
Cl2 Ta Cl1 150.4(2) . . ?
O1 Ta C19 76.7(7) . . ?
O2 Ta C19 126.6(7) . . ?
N1 Ta C19 152.9(8) . . ?
C15 Ta C19 32.2(10) . . ?
Cl2 Ta C19 87.9(9) . . ?
Cl1 Ta C19 118.5(8) . . ?
O1 Ta C16 109.8(5) . . ?
O2 Ta C16 92.4(5) . . ?
N1 Ta C16 150.0(5) . . ?
C15 Ta C16 33.9(5) . . ?
Cl2 Ta C16 132.1(4) . . ?
Cl1 Ta C16 77.1(4) . . ?
C19 Ta C16 55.1(9) . . ?
O1 Ta C18 108.2(5) . . ?
O2 Ta C18 93.0(5) . . ?
N1 Ta C18 149.1(6) . . ?
C15 Ta C18 55.7(6) . . ?
Cl2 Ta C18 76.5(4) . . ?
Cl1 Ta C18 132.8(4) . . ?
C19 Ta C18 34.6(8) . . ?
C16 Ta C18 55.7(5) . . ?
O1 Ta C17 130.2(5) . . ?
O2 Ta C17 74.5(5) . . ?
N1 Ta C17 148.5(5) . . ?
C15 Ta C17 55.1(5) . . ?
Cl2 Ta C17 102.6(4) . . ?
Cl1 Ta C17 103.8(4) . . ?
C19 Ta C17 55.1(7) . . ?
C16 Ta C17 33.1(5) . . ?
C18 Ta C17 33.1(5) . . ?
C7 N1 C8 120.6(16) . . ?
C7 N1 Ta 128.0(13) . . ?
C8 N1 Ta 111.4(11) . . ?
O1 C1 C2 123.2(13) . . ?
O1 C1 C6 117.7(15) . . ?
C2 C1 C6 119.0(14) . . ?
C1 O1 Ta 138.9(10) . . ?
C9 O2 Ta 123.3(9) . . ?
C1 C2 C3 120.0(14) . . ?
C1 C2 C7 122.3(14) . . ?
C3 C2 C7 117.6(15) . . ?
C4 C3 C2 120.4(16) . . ?
C4 C3 H3A 119.8 . . ?
C2 C3 H3A 119.8 . . ?
C5 C4 C3 118.6(15) . . ?
C5 C4 H4A 120.7 . . ?
C3 C4 H4A 120.7 . . ?
C6 C5 C4 121.2(15) . . ?
C6 C5 H5A 119.4 . . ?
C4 C5 H5A 119.4 . . ?
C5 C6 C1 120.7(15) . . ?
C5 C6 H6A 119.7 . . ?
C1 C6 H6A 119.7 . . ?
N1 C7 C2 126.3(17) . . ?
N1 C7 H7A 116.9 . . ?
C2 C7 H7A 116.9 . . ?
C9 C8 C13 120.0(15) . . ?
C9 C8 N1 113.1(15) . . ?
C13 C8 N1 126.8(14) . . ?
O2 C9 C8 118.1(14) . . ?
O2 C9 C10 122.0(14) . . ?
C8 C9 C10 119.9(15) . . ?
C9 C10 C11 120.4(15) . . ?
C9 C10 H10A 119.8 . . ?
C11 C10 H10A 119.8 . . ?
C12 C11 C10 119.2(15) . . ?
C12 C11 H11A 120.4 . . ?
C10 C11 H11A 120.4 . . ?
C13 C12 C11 120.3(17) . . ?
C13 C12 H12A 119.8 . . ?
C11 C12 H12A 119.8 . . ?
C12 C13 C8 120.2(16) . . ?
C12 C13 H13A 119.9 . . ?
C8 C13 H13A 119.9 . . ?
C19 C15 C16 109.7(18) . . ?
C19 C15 C20 125.5(19) . . ?
C16 C15 C20 124.7(17) . . ?
C19 C15 Ta 74.7(16) . . ?
C16 C15 Ta 74.7(10) . . ?
C20 C15 Ta 120.1(12) . . ?
C17 C16 C15 106.7(14) . . ?
C17 C16 C21 125.2(15) . . ?
C15 C16 C21 126.8(15) . . ?
C17 C16 Ta 75.1(8) . . ?
C15 C16 Ta 71.4(10) . . ?
C21 C16 Ta 128.7(11) . . ?
C16 C17 C18 109.2(14) . . ?
C16 C17 C22 124.6(15) . . ?
C18 C17 C22 126.1(15) . . ?
C16 C17 Ta 71.8(9) . . ?
C18 C17 Ta 72.5(8) . . ?
C22 C17 Ta 124.9(10) . . ?
C17 C18 C19 105(2) . . ?
C17 C18 C23 126.7(16) . . ?
C19 C18 C23 127(2) . . ?
C17 C18 Ta 74.4(8) . . ?
C19 C18 Ta 71.1(14) . . ?
C23 C18 Ta 127.3(12) . . ?
C15 C19 C18 109(2) . . ?
C15 C19 C24 130(2) . . ?
C18 C19 C24 120(3) . . ?
C15 C19 Ta 73.2(17) . . ?
C18 C19 Ta 74.3(13) . . ?
C24 C19 Ta 118.9(18) . . ?
C15 C20 H20A 109.5 . . ?
C15 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C15 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C16 C21 H21A 109.5 . . ?
C16 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C16 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C17 C22 H22A 109.5 . . ?
C17 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C17 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C18 C23 H23A 109.5 . . ?
C18 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C18 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C19 C24 H24A 109.5 . . ?
C19 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C19 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

_refine_diff_density_max         2.631
_refine_diff_density_min         -1.960
_refine_diff_density_rms         0.193



