#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/31/56/4315669.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4315669
loop_
_publ_author_name
'Nathalie Lavoie'
'Serge I. Gorelsky'
'Zhixian Liu'
'Tara J. Burchell'
'Glenn P. A. Yap'
'Darrin S. Richeson'
_publ_section_title
;
 Disubstituted 1,8-Diamidonaphthalene Ligands as a Flexible, Responsive,
 and Reactive Framework for Tantalum Complexes
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              5231
_journal_page_last               5240
_journal_paper_doi               10.1021/ic1003963
_journal_volume                  49
_journal_year                    2010
_chemical_formula_sum            'C25 H25 N2 Ta'
_chemical_formula_weight         534.42
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                96.708(2)
_cell_angle_beta                 113.601(2)
_cell_angle_gamma                113.073(2)
_cell_formula_units_Z            2
_cell_length_a                   10.5074(11)
_cell_length_b                   10.5509(11)
_cell_length_c                   11.9869(13)
_cell_measurement_reflns_used    'reflections from 60 data frames'
_cell_measurement_temperature    203(2)
_cell_measurement_theta_max      28.29
_cell_measurement_theta_min      1.47
_cell_volume                     1059.6(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      203(2)
_diffrn_detector_area_resol_mean 836.6
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.885
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0222
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4631
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.26
_diffrn_reflns_theta_min         2.22
_diffrn_standards_decay_%        <1
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         '50 standard frames at start and end'
_exptl_absorpt_coefficient_mu    5.198
_exptl_absorpt_correction_T_max  0.928067
_exptl_absorpt_correction_T_min  0.627688
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.675
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             524
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         1.515
_refine_diff_density_min         -1.339
_refine_diff_density_rms         0.121
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         4631
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0368
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1400P)²+3.4173P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1669
_refine_ls_wR_factor_ref         0.1691
_reflns_number_gt                4402
_reflns_number_total             4631
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic1003963_si_002_2.cif
_cod_data_source_block           dr2012a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_cell_volume        1059.64(19)
_cod_database_code               4315669
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
Ta Ta 0.62380(3) 0.27371(3) 0.23818(3) 0.03032(16) Uani 1 1 d . . .
N1 N 0.5769(7) 0.2895(7) 0.3891(6) 0.0289(13) Uani 1 1 d . . .
N2 N 0.5575(8) 0.4194(7) 0.1989(6) 0.0302(13) Uani 1 1 d . . .
C1 C 0.7338(10) 0.4297(9) 0.6183(8) 0.0357(17) Uani 1 1 d . . .
H1A H 0.7299 0.5118 0.5974 0.043 Uiso 1 1 calc R . .
C2 C 0.8117(11) 0.4413(11) 0.7450(9) 0.047(2) Uani 1 1 d . . .
H2A H 0.8649 0.5320 0.8092 0.057 Uiso 1 1 calc R . .
C3 C 0.8128(12) 0.3210(12) 0.7795(9) 0.047(2) Uani 1 1 d . . .
H3A H 0.8600 0.3272 0.8666 0.056 Uiso 1 1 calc R . .
C4 C 0.7430(12) 0.1911(12) 0.6829(10) 0.049(2) Uani 1 1 d . . .
H4A H 0.7464 0.1091 0.7042 0.058 Uiso 1 1 calc R . .
C5 C 0.6676(11) 0.1816(10) 0.5541(9) 0.0404(19) Uani 1 1 d . . .
H5A H 0.6207 0.0931 0.4890 0.048 Uiso 1 1 calc R . .
C6 C 0.6614(9) 0.3017(9) 0.5212(7) 0.0300(15) Uani 1 1 d . . .
C7 C 0.4186(9) 0.2643(8) 0.3464(7) 0.0281(14) Uani 1 1 d . . .
C8 C 0.3453(10) 0.2214(9) 0.4194(8) 0.0340(16) Uani 1 1 d . . .
H8A H 0.4065 0.2281 0.5046 0.041 Uiso 1 1 calc R . .
C9 C 0.1812(10) 0.1680(10) 0.3684(9) 0.0391(18) Uani 1 1 d . . .
H9A H 0.1359 0.1453 0.4218 0.047 Uiso 1 1 calc R . .
C10 C 0.0845(9) 0.1481(10) 0.2403(7) 0.0363(18) Uani 1 1 d . . .
H10A H -0.0265 0.1007 0.2038 0.044 Uiso 1 1 calc R . .
C11 C 0.1566(9) 0.2003(8) 0.1679(7) 0.0284(14) Uani 1 1 d . . .
C12 C 0.3264(9) 0.2691(8) 0.2213(7) 0.0269(14) Uani 1 1 d . . .
C13 C 0.3910(9) 0.3354(9) 0.1443(8) 0.0299(15) Uani 1 1 d . . .
C14 C 0.2952(10) 0.3192(10) 0.0209(8) 0.0372(17) Uani 1 1 d . . .
H14A H 0.3410 0.3594 -0.0282 0.045 Uiso 1 1 calc R . .
C15 C 0.1264(11) 0.2427(12) -0.0361(8) 0.042(2) Uani 1 1 d . . .
H15A H 0.0612 0.2301 -0.1222 0.050 Uiso 1 1 calc R . .
C16 C 0.0625(10) 0.1884(10) 0.0383(8) 0.0382(18) Uani 1 1 d . . .
H16A H -0.0483 0.1412 0.0023 0.046 Uiso 1 1 calc R . .
C17 C 0.5481(11) 0.6491(10) 0.2261(9) 0.0377(18) Uani 1 1 d . . .
H17A H 0.4369 0.5985 0.1867 0.045 Uiso 1 1 calc R . .
C18 C 0.6275(13) 0.8007(11) 0.2689(11) 0.048(2) Uani 1 1 d . . .
H18A H 0.5697 0.8514 0.2606 0.057 Uiso 1 1 calc R . .
C19 C 0.7894(13) 0.8769(10) 0.3231(10) 0.046(2) Uani 1 1 d . . .
H19A H 0.8416 0.9791 0.3488 0.056 Uiso 1 1 calc R . .
C20 C 0.8747(11) 0.8040(10) 0.3399(9) 0.0429(19) Uani 1 1 d . . .
H20A H 0.9856 0.8565 0.3775 0.051 Uiso 1 1 calc R . .
C21 C 0.7978(10) 0.6515(9) 0.3013(8) 0.0346(16) Uani 1 1 d . . .
H21A H 0.8576 0.6023 0.3158 0.042 Uiso 1 1 calc R . .
C22 C 0.6313(9) 0.5718(9) 0.2409(8) 0.0312(15) Uani 1 1 d . . .
C23 C 0.4507(12) 0.0543(10) 0.1230(10) 0.045(2) Uani 1 1 d . . .
H23A H 0.5013 -0.0065 0.1330 0.067 Uiso 1 1 calc R . .
H23B H 0.4008 0.0485 0.0334 0.067 Uiso 1 1 calc R . .
H23C H 0.3711 0.0206 0.1500 0.067 Uiso 1 1 calc R . .
C24 C 0.7567(12) 0.3194(12) 0.1333(11) 0.049(2) Uani 1 1 d . . .
H24A H 0.7824 0.2422 0.1194 0.073 Uiso 1 1 calc R . .
H24B H 0.8539 0.4115 0.1831 0.073 Uiso 1 1 calc R . .
H24C H 0.6930 0.3249 0.0510 0.073 Uiso 1 1 calc R . .
C25 C 0.8440(13) 0.2941(14) 0.3790(11) 0.057(3) Uani 1 1 d . . .
H25A H 0.8237 0.2052 0.4010 0.085 Uiso 1 1 calc R . .
H25B H 0.8920 0.3755 0.4556 0.085 Uiso 1 1 calc R . .
H25C H 0.9154 0.3108 0.3437 0.085 Uiso 1 1 calc R . .
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'
Ta Ta -0.7052 6.5227 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Ta N1 87.3(3) . . ?
N2 Ta C23 115.5(3) . . ?
N1 Ta C23 99.9(3) . . ?
N2 Ta C25 131.6(4) . . ?
N1 Ta C25 84.6(4) . . ?
C23 Ta C25 112.9(4) . . ?
N2 Ta C24 92.5(3) . . ?
N1 Ta C24 159.3(4) . . ?
C23 Ta C24 98.8(4) . . ?
C25 Ta C24 80.0(4) . . ?
N2 Ta C13 32.0(2) . . ?
N1 Ta C13 79.4(2) . . ?
C23 Ta C13 86.2(3) . . ?
C25 Ta C13 157.0(4) . . ?
C24 Ta C13 110.7(3) . . ?
C6 N1 C7 114.6(6) . . ?
C6 N1 Ta 133.4(5) . . ?
C7 N1 Ta 111.5(5) . . ?
C22 N2 C13 120.6(7) . . ?
C22 N2 Ta 135.5(5) . . ?
C13 N2 Ta 101.1(5) . . ?
C6 C1 C2 121.7(8) . . ?
C3 C2 C1 120.7(9) . . ?
C2 C3 C4 118.5(9) . . ?
C5 C4 C3 120.2(9) . . ?
C4 C5 C6 120.5(9) . . ?
C1 C6 C5 118.3(8) . . ?
C1 C6 N1 121.3(7) . . ?
C5 C6 N1 120.3(8) . . ?
C8 C7 N1 120.5(7) . . ?
C8 C7 C12 118.4(7) . . ?
N1 C7 C12 120.8(7) . . ?
C7 C8 C9 121.3(8) . . ?
C10 C9 C8 121.2(8) . . ?
C9 C10 C11 118.3(7) . . ?
C10 C11 C16 120.1(7) . . ?
C10 C11 C12 121.6(7) . . ?
C16 C11 C12 118.3(7) . . ?
C11 C12 C13 117.4(7) . . ?
C11 C12 C7 117.7(7) . . ?
C13 C12 C7 124.9(7) . . ?
C14 C13 N2 119.5(7) . . ?
C14 C13 C12 121.2(7) . . ?
N2 C13 C12 119.3(7) . . ?
C14 C13 Ta 130.1(6) . . ?
N2 C13 Ta 46.9(4) . . ?
C12 C13 Ta 91.6(5) . . ?
C13 C14 C15 121.7(8) . . ?
C16 C15 C14 118.1(8) . . ?
C15 C16 C11 122.9(8) . . ?
C22 C17 C18 120.7(9) . . ?
C19 C18 C17 120.7(9) . . ?
C18 C19 C20 120.0(9) . . ?
C19 C20 C21 120.4(9) . . ?
C20 C21 C22 120.1(8) . . ?
C17 C22 N2 123.2(8) . . ?
C17 C22 C21 118.0(8) . . ?
N2 C22 C21 118.8(7) . . ?
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 N2 1.954(7) . ?
Ta N1 2.061(7) . ?
Ta C23 2.125(10) . ?
Ta C25 2.156(11) . ?
Ta C24 2.187(10) . ?
Ta C13 2.624(8) . ?
N1 C6 1.432(9) . ?
N1 C7 1.428(10) . ?
N2 C22 1.401(10) . ?
N2 C13 1.417(10) . ?
C1 C6 1.370(12) . ?
C1 C2 1.369(13) . ?
C2 C3 1.384(14) . ?
C3 C4 1.385(16) . ?
C4 C5 1.394(13) . ?
C5 C6 1.388(11) . ?
C7 C8 1.386(11) . ?
C7 C12 1.443(10) . ?
C8 C9 1.407(12) . ?
C9 C10 1.394(13) . ?
C10 C11 1.394(12) . ?
C11 C16 1.426(11) . ?
C11 C12 1.443(10) . ?
C12 C13 1.443(10) . ?
C13 C14 1.358(11) . ?
C14 C15 1.429(12) . ?
C15 C16 1.367(13) . ?
C17 C22 1.388(12) . ?
C17 C18 1.392(13) . ?
C18 C19 1.372(15) . ?
C19 C20 1.366(14) . ?
C20 C21 1.401(12) . ?
C21 C22 1.409(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
N2 Ta N1 C6 -134.5(7) . . . . ?
C23 Ta N1 C6 110.1(7) . . . . ?
C25 Ta N1 C6 -2.3(8) . . . . ?
C24 Ta N1 C6 -44.5(13) . . . . ?
C13 Ta N1 C6 -165.7(7) . . . . ?
N2 Ta N1 C7 54.8(5) . . . . ?
C23 Ta N1 C7 -60.6(6) . . . . ?
C25 Ta N1 C7 -172.9(6) . . . . ?
C24 Ta N1 C7 144.8(9) . . . . ?
C13 Ta N1 C7 23.6(5) . . . . ?
N1 Ta N2 C22 85.7(7) . . . . ?
C23 Ta N2 C22 -174.5(7) . . . . ?
C25 Ta N2 C22 5.3(10) . . . . ?
C24 Ta N2 C22 -73.5(8) . . . . ?
C13 Ta N2 C22 159.8(10) . . . . ?
N1 Ta N2 C13 -74.1(5) . . . . ?
C23 Ta N2 C13 25.7(6) . . . . ?
C25 Ta N2 C13 -154.5(6) . . . . ?
C24 Ta N2 C13 126.7(5) . . . . ?
C6 C1 C2 C3 -3.3(15) . . . . ?
C1 C2 C3 C4 4.4(16) . . . . ?
C2 C3 C4 C5 -2.7(16) . . . . ?
C3 C4 C5 C6 -0.1(15) . . . . ?
C2 C1 C6 C5 0.4(14) . . . . ?
C2 C1 C6 N1 178.5(8) . . . . ?
C4 C5 C6 C1 1.3(14) . . . . ?
C4 C5 C6 N1 -176.8(8) . . . . ?
C7 N1 C6 C1 -82.0(9) . . . . ?
Ta N1 C6 C1 107.6(9) . . . . ?
C7 N1 C6 C5 96.0(9) . . . . ?
Ta N1 C6 C5 -74.4(10) . . . . ?
C6 N1 C7 C8 -14.4(10) . . . . ?
Ta N1 C7 C8 158.1(6) . . . . ?
C6 N1 C7 C12 171.6(7) . . . . ?
Ta N1 C7 C12 -15.8(8) . . . . ?
N1 C7 C8 C9 -167.1(8) . . . . ?
C12 C7 C8 C9 7.0(12) . . . . ?
C7 C8 C9 C10 3.8(14) . . . . ?
C8 C9 C10 C11 -8.4(14) . . . . ?
C9 C10 C11 C16 -177.0(8) . . . . ?
C9 C10 C11 C12 2.1(13) . . . . ?
C10 C11 C12 C13 -172.6(8) . . . . ?
C16 C11 C12 C13 6.5(11) . . . . ?
C10 C11 C12 C7 8.5(11) . . . . ?
C16 C11 C12 C7 -172.4(7) . . . . ?
C8 C7 C12 C11 -12.8(10) . . . . ?
N1 C7 C12 C11 161.3(7) . . . . ?
C8 C7 C12 C13 168.3(8) . . . . ?
N1 C7 C12 C13 -17.6(11) . . . . ?
C22 N2 C13 C14 77.3(10) . . . . ?
Ta N2 C13 C14 -119.0(7) . . . . ?
C22 N2 C13 C12 -102.3(8) . . . . ?
Ta N2 C13 C12 61.3(8) . . . . ?
C22 N2 C13 Ta -163.7(8) . . . . ?
C11 C12 C13 C14 -7.4(12) . . . . ?
C7 C12 C13 C14 171.5(8) . . . . ?
C11 C12 C13 N2 172.3(7) . . . . ?
C7 C12 C13 N2 -8.9(12) . . . . ?
C11 C12 C13 Ta -147.9(6) . . . . ?
C7 C12 C13 Ta 31.0(8) . . . . ?
N2 Ta C13 C14 95.4(9) . . . . ?
N1 Ta C13 C14 -162.4(8) . . . . ?
C23 Ta C13 C14 -61.5(8) . . . . ?
C25 Ta C13 C14 151.0(11) . . . . ?
C24 Ta C13 C14 36.5(9) . . . . ?
N1 Ta C13 N2 102.2(5) . . . . ?
C23 Ta C13 N2 -156.9(5) . . . . ?
C25 Ta C13 N2 55.6(11) . . . . ?
C24 Ta C13 N2 -58.9(6) . . . . ?
N2 Ta C13 C12 -130.0(7) . . . . ?
N1 Ta C13 C12 -27.8(5) . . . . ?
C23 Ta C13 C12 73.0(5) . . . . ?
C25 Ta C13 C12 -74.4(11) . . . . ?
C24 Ta C13 C12 171.1(5) . . . . ?
N2 C13 C14 C15 -176.3(8) . . . . ?
C12 C13 C14 C15 3.4(14) . . . . ?
Ta C13 C14 C15 127.0(8) . . . . ?
C13 C14 C15 C16 1.6(14) . . . . ?
C14 C15 C16 C11 -2.3(15) . . . . ?
C10 C11 C16 C15 177.3(9) . . . . ?
C12 C11 C16 C15 -1.8(13) . . . . ?
C22 C17 C18 C19 2.0(15) . . . . ?
C17 C18 C19 C20 -2.4(16) . . . . ?
C18 C19 C20 C21 0.3(15) . . . . ?
C19 C20 C21 C22 2.2(13) . . . . ?
C18 C17 C22 N2 -179.5(8) . . . . ?
C18 C17 C22 C21 0.5(13) . . . . ?
C13 N2 C22 C17 -3.6(11) . . . . ?
Ta N2 C22 C17 -160.4(7) . . . . ?
C13 N2 C22 C21 176.4(7) . . . . ?
Ta N2 C22 C21 19.6(11) . . . . ?
C20 C21 C22 C17 -2.5(12) . . . . ?
C20 C21 C22 N2 177.5(7) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30660991
