# Electronic Supplementary Material (ESI) for Chemical Science.
# 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
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  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_(1)
_chemical_name_common            'Complex 2a'
_chemical_melting_point          ?
_chemical_formula_moiety         'C39 H55 F N3 Nb'
_chemical_formula_sum            'C39 H55 F N3 Nb'
_chemical_formula_weight         677.77

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'
Nb Nb -2.0727 0.6215 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.795(5)
_cell_length_b                   12.323(5)
_cell_length_c                   13.680(5)
_cell_angle_alpha                79.363(5)
_cell_angle_beta                 87.377(5)
_cell_angle_gamma                88.428(5)
_cell_volume                     1786.3(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9878
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      25.44

_exptl_crystal_description       rode
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             720
_exptl_absorpt_coefficient_mu    0.372
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8654
_exptl_absorpt_correction_T_max  0.8966
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-I CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.366
_diffrn_reflns_number            27323
_diffrn_reflns_av_R_equivalents  0.0168
_diffrn_reflns_av_sigmaI/netI    0.0155
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.52
_diffrn_reflns_theta_max         25.44
_reflns_number_total             6588
_reflns_number_gt                6259
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2 v.2011.4'
_computing_cell_refinement       'Bruker APEX2 v.2011.4'
_computing_data_reduction        'Bruker APEX2 v.2011.4'
_computing_structure_solution    SIR-2004
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ORTEP-32
_computing_publication_material  WinGX

_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)+(0.0231P)²+1.3452P] 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         6588
_refine_ls_number_parameters     410
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0240
_refine_ls_R_factor_gt           0.0224
_refine_ls_wR_factor_ref         0.0587
_refine_ls_wR_factor_gt          0.0576
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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
C1 C -0.02922(15) 0.29992(15) 0.39217(13) 0.0249(4) Uani 1 1 d . . .
H1A H -0.0126 0.2552 0.4574 0.037 Uiso 1 1 calc R . .
H1B H -0.1145 0.2884 0.3752 0.037 Uiso 1 1 calc R . .
H1C H -0.0185 0.3781 0.3943 0.037 Uiso 1 1 calc R . .
C2 C 0.05992(14) 0.26613(13) 0.31444(12) 0.0177(3) Uani 1 1 d . . .
C3 C 0.00918(15) 0.21853(13) 0.24208(12) 0.0194(3) Uani 1 1 d . . .
H3 H -0.0784 0.2256 0.2381 0.023 Uiso 1 1 calc R . .
C4 C 0.07015(15) 0.16066(13) 0.17306(12) 0.0182(3) Uani 1 1 d . . .
C5 C -0.01234(16) 0.09166(15) 0.12328(13) 0.0260(4) Uani 1 1 d . . .
H5A H -0.0251 0.1290 0.0547 0.039 Uiso 1 1 calc R . .
H5B H -0.0926 0.0821 0.1600 0.039 Uiso 1 1 calc R . .
H5C H 0.0272 0.0192 0.1229 0.039 Uiso 1 1 calc R . .
C6 C 0.21799(14) 0.30614(13) 0.41714(11) 0.0168(3) Uani 1 1 d . . .
C7 C 0.23485(15) 0.21767(13) 0.49692(12) 0.0188(3) Uani 1 1 d . . .
C8 C 0.27146(16) 0.24101(15) 0.58700(12) 0.0243(4) Uani 1 1 d . . .
H8 H 0.2850 0.1820 0.6411 0.029 Uiso 1 1 calc R . .
C9 C 0.28850(18) 0.34832(16) 0.59918(13) 0.0288(4) Uani 1 1 d . . .
H9 H 0.3147 0.3627 0.6608 0.035 Uiso 1 1 calc R . .
C10 C 0.26733(17) 0.43441(15) 0.52162(13) 0.0260(4) Uani 1 1 d . . .
H10 H 0.2776 0.5081 0.5310 0.031 Uiso 1 1 calc R . .
C11 C 0.23106(15) 0.41586(14) 0.42936(12) 0.0203(3) Uani 1 1 d . . .
C12 C 0.20692(16) 0.51484(13) 0.34777(12) 0.0232(4) Uani 1 1 d . . .
H12 H 0.1781 0.4867 0.2888 0.028 Uiso 1 1 calc R . .
C13 C 0.10506(18) 0.59215(15) 0.37947(14) 0.0316(4) Uani 1 1 d . . .
H13A H 0.0305 0.5497 0.4027 0.047 Uiso 1 1 calc R . .
H13B H 0.0855 0.6500 0.3226 0.047 Uiso 1 1 calc R . .
H13C H 0.1341 0.6261 0.4334 0.047 Uiso 1 1 calc R . .
C14 C 0.32583(18) 0.57917(14) 0.31568(14) 0.0284(4) Uani 1 1 d . . .
H14A H 0.3530 0.6118 0.3710 0.043 Uiso 1 1 calc R . .
H14B H 0.3097 0.6379 0.2586 0.043 Uiso 1 1 calc R . .
H14C H 0.3909 0.5290 0.2969 0.043 Uiso 1 1 calc R . .
C15 C 0.21579(15) 0.09796(13) 0.48798(12) 0.0210(3) Uani 1 1 d . . .
H15 H 0.1753 0.0976 0.4238 0.025 Uiso 1 1 calc R . .
C16 C 0.34097(16) 0.03720(14) 0.48486(14) 0.0263(4) Uani 1 1 d . . .
H16A H 0.3909 0.0723 0.4265 0.039 Uiso 1 1 calc R . .
H16B H 0.3275 -0.0401 0.4806 0.039 Uiso 1 1 calc R . .
H16C H 0.3847 0.0405 0.5454 0.039 Uiso 1 1 calc R . .
C17 C 0.13138(18) 0.03774(16) 0.57268(15) 0.0319(4) Uani 1 1 d . . .
H17A H 0.1719 0.0327 0.6361 0.048 Uiso 1 1 calc R . .
H17B H 0.1157 -0.0367 0.5611 0.048 Uiso 1 1 calc R . .
H17C H 0.0525 0.0787 0.5751 0.048 Uiso 1 1 calc R . .
C18 C 0.24143(15) 0.09301(13) 0.08707(12) 0.0192(3) Uani 1 1 d . . .
C19 C 0.30031(16) -0.00672(14) 0.12896(13) 0.0222(3) Uani 1 1 d . . .
C20 C 0.34873(17) -0.07468(15) 0.06489(14) 0.0293(4) Uani 1 1 d . . .
H20 H 0.3874 -0.1431 0.0919 0.035 Uiso 1 1 calc R . .
C21 C 0.34138(18) -0.04427(16) -0.03670(14) 0.0313(4) Uani 1 1 d . . .
H21 H 0.3743 -0.0917 -0.0792 0.038 Uiso 1 1 calc R . .
C22 C 0.28597(17) 0.05550(15) -0.07669(13) 0.0278(4) Uani 1 1 d . . .
H22 H 0.2822 0.0762 -0.1469 0.033 Uiso 1 1 calc R . .
C23 C 0.23532(16) 0.12675(14) -0.01625(12) 0.0225(4) Uani 1 1 d . . .
C24 C 0.18447(18) 0.23940(15) -0.06376(13) 0.0273(4) Uani 1 1 d . . .
H24 H 0.1416 0.2732 -0.0100 0.033 Uiso 1 1 calc R . .
C25 C 0.0899(2) 0.23329(18) -0.14267(14) 0.0370(5) Uani 1 1 d . . .
H25A H 0.1301 0.2017 -0.1970 0.055 Uiso 1 1 calc R . .
H25B H 0.0580 0.3077 -0.1689 0.055 Uiso 1 1 calc R . .
H25C H 0.0212 0.1865 -0.1126 0.055 Uiso 1 1 calc R . .
C26 C 0.2918(2) 0.31461(17) -0.10850(14) 0.0367(5) Uani 1 1 d . . .
H26A H 0.3496 0.3200 -0.0565 0.055 Uiso 1 1 calc R . .
H26B H 0.2588 0.3883 -0.1358 0.055 Uiso 1 1 calc R . .
H26C H 0.3354 0.2835 -0.1617 0.055 Uiso 1 1 calc R . .
C27 C 0.31157(16) -0.04001(14) 0.24091(13) 0.0240(4) Uani 1 1 d . . .
H27 H 0.3114 0.0295 0.2688 0.029 Uiso 1 1 calc R . .
C28 C 0.43220(18) -0.10282(16) 0.27003(15) 0.0319(4) Uani 1 1 d . . .
H28A H 0.4327 -0.1743 0.2483 0.048 Uiso 1 1 calc R . .
H28B H 0.4385 -0.1147 0.3425 0.048 Uiso 1 1 calc R . .
H28C H 0.5028 -0.0597 0.2380 0.048 Uiso 1 1 calc R . .
C29 C 0.19965(18) -0.10609(17) 0.28848(15) 0.0357(4) Uani 1 1 d . . .
H29A H 0.1243 -0.0600 0.2778 0.054 Uiso 1 1 calc R . .
H29B H 0.2107 -0.1291 0.3601 0.054 Uiso 1 1 calc R . .
H29C H 0.1921 -0.1715 0.2581 0.054 Uiso 1 1 calc R . .
C30 C 0.57066(15) 0.30168(14) 0.31665(12) 0.0197(3) Uani 1 1 d . . .
C31 C 0.55865(16) 0.29710(16) 0.42915(13) 0.0267(4) Uani 1 1 d . . .
H31A H 0.5167 0.3646 0.4429 0.040 Uiso 1 1 calc R . .
H31B H 0.6414 0.2910 0.4566 0.040 Uiso 1 1 calc R . .
H31C H 0.5101 0.2328 0.4601 0.040 Uiso 1 1 calc R . .
C32 C 0.63503(16) 0.19665(14) 0.29285(14) 0.0252(4) Uani 1 1 d . . .
H32A H 0.5848 0.1325 0.3211 0.038 Uiso 1 1 calc R . .
H32B H 0.7169 0.1881 0.3217 0.038 Uiso 1 1 calc R . .
H32C H 0.6445 0.2023 0.2205 0.038 Uiso 1 1 calc R . .
C33 C 0.64342(16) 0.40358(14) 0.26636(13) 0.0245(4) Uani 1 1 d . . .
H33A H 0.6500 0.4058 0.1943 0.037 Uiso 1 1 calc R . .
H33B H 0.7267 0.3996 0.2927 0.037 Uiso 1 1 calc R . .
H33C H 0.6001 0.4705 0.2800 0.037 Uiso 1 1 calc R . .
C34 C 0.28832(15) 0.44587(13) 0.11713(12) 0.0199(3) Uani 1 1 d . . .
C35 C 0.37816(16) 0.52526(14) 0.08098(13) 0.0242(4) Uani 1 1 d . . .
H35 H 0.4620 0.5103 0.0983 0.029 Uiso 1 1 calc R . .
C36 C 0.34770(18) 0.62506(15) 0.02056(14) 0.0292(4) Uani 1 1 d . . .
H36 H 0.4104 0.6767 -0.0046 0.035 Uiso 1 1 calc R . .
C37 C 0.22552(19) 0.64862(16) -0.00266(14) 0.0330(4) Uani 1 1 d . . .
H37 H 0.2040 0.7173 -0.0430 0.040 Uiso 1 1 calc R . .
C38 C 0.13434(18) 0.57280(16) 0.03245(14) 0.0315(4) Uani 1 1 d . . .
H38 H 0.0504 0.5896 0.0166 0.038 Uiso 1 1 calc R . .
C39 C 0.16585(16) 0.47199(15) 0.09097(13) 0.0253(4) Uani 1 1 d . . .
H39 H 0.1029 0.4198 0.1136 0.030 Uiso 1 1 calc R . .
N1 N 0.18367(12) 0.28120(10) 0.32177(9) 0.0151(3) Uani 1 1 d . . .
N2 N 0.19102(12) 0.16449(10) 0.15354(9) 0.0161(3) Uani 1 1 d . . .
N3 N 0.44846(12) 0.31025(11) 0.27467(10) 0.0174(3) Uani 1 1 d . . .
F1 F 0.42738(9) 0.21717(8) 0.11282(8) 0.0280(2) Uani 1 1 d . . .
Nb1 Nb 0.322817(12) 0.284245(11) 0.204560(10) 0.01360(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
C1 C2 1.509(2) . ?
C2 N1 1.365(2) . ?
C2 C3 1.380(2) . ?
C3 C4 1.414(2) . ?
C4 N2 1.320(2) . ?
C4 C5 1.513(2) . ?
C6 C11 1.404(2) . ?
C6 C7 1.407(2) . ?
C6 N1 1.460(2) . ?
C7 C8 1.393(2) . ?
C7 C15 1.523(2) . ?
C8 C9 1.381(3) . ?
C9 C10 1.377(3) . ?
C10 C11 1.398(2) . ?
C11 C12 1.519(2) . ?
C12 C14 1.531(2) . ?
C12 C13 1.535(2) . ?
C15 C16 1.530(2) . ?
C15 C17 1.532(2) . ?
C18 C23 1.402(2) . ?
C18 C19 1.405(2) . ?
C18 N2 1.457(2) . ?
C19 C20 1.396(2) . ?
C19 C27 1.520(2) . ?
C20 C21 1.376(3) . ?
C21 C22 1.382(3) . ?
C22 C23 1.398(2) . ?
C23 C24 1.519(3) . ?
C24 C25 1.532(2) . ?
C24 C26 1.536(3) . ?
C27 C28 1.527(3) . ?
C27 C29 1.527(3) . ?
C30 N3 1.456(2) . ?
C30 C31 1.529(2) . ?
C30 C32 1.533(2) . ?
C30 C33 1.534(2) . ?
C34 C39 1.399(2) . ?
C34 C35 1.404(2) . ?
C34 Nb1 2.1580(18) . ?
C35 C36 1.390(3) . ?
C36 C37 1.381(3) . ?
C37 C38 1.384(3) . ?
C38 C39 1.391(3) . ?
N1 Nb1 2.1422(14) . ?
N2 Nb1 2.2968(14) . ?
N3 Nb1 1.7659(14) . ?
F1 Nb1 1.9325(11) . ?

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
N1 C2 C3 124.70(15) . . ?
N1 C2 C1 118.62(14) . . ?
C3 C2 C1 116.66(14) . . ?
C2 C3 C4 128.64(15) . . ?
N2 C4 C3 122.94(14) . . ?
N2 C4 C5 121.56(15) . . ?
C3 C4 C5 115.49(14) . . ?
C11 C6 C7 120.95(14) . . ?
C11 C6 N1 120.71(14) . . ?
C7 C6 N1 118.33(14) . . ?
C8 C7 C6 118.42(15) . . ?
C8 C7 C15 119.05(15) . . ?
C6 C7 C15 122.52(14) . . ?
C9 C8 C7 121.22(16) . . ?
C10 C9 C8 119.76(16) . . ?
C9 C10 C11 121.49(16) . . ?
C10 C11 C6 118.07(15) . . ?
C10 C11 C12 118.64(15) . . ?
C6 C11 C12 123.29(14) . . ?
C11 C12 C14 111.10(15) . . ?
C11 C12 C13 111.99(14) . . ?
C14 C12 C13 109.98(14) . . ?
C7 C15 C16 110.16(14) . . ?
C7 C15 C17 112.08(14) . . ?
C16 C15 C17 110.34(14) . . ?
C23 C18 C19 121.59(15) . . ?
C23 C18 N2 119.91(15) . . ?
C19 C18 N2 118.43(14) . . ?
C20 C19 C18 118.17(16) . . ?
C20 C19 C27 120.68(16) . . ?
C18 C19 C27 121.16(15) . . ?
C21 C20 C19 121.17(18) . . ?
C20 C21 C22 119.84(17) . . ?
C21 C22 C23 121.57(17) . . ?
C22 C23 C18 117.61(16) . . ?
C22 C23 C24 119.61(16) . . ?
C18 C23 C24 122.64(15) . . ?
C23 C24 C25 113.00(15) . . ?
C23 C24 C26 109.82(16) . . ?
C25 C24 C26 110.50(16) . . ?
C19 C27 C28 113.16(15) . . ?
C19 C27 C29 111.06(15) . . ?
C28 C27 C29 110.67(15) . . ?
N3 C30 C31 110.25(13) . . ?
N3 C30 C32 107.87(13) . . ?
C31 C30 C32 110.69(14) . . ?
N3 C30 C33 107.65(13) . . ?
C31 C30 C33 110.30(14) . . ?
C32 C30 C33 110.00(14) . . ?
C39 C34 C35 117.18(15) . . ?
C39 C34 Nb1 116.81(12) . . ?
C35 C34 Nb1 125.96(13) . . ?
C36 C35 C34 121.72(17) . . ?
C37 C36 C35 119.47(17) . . ?
C36 C37 C38 120.37(17) . . ?
C37 C38 C39 119.87(17) . . ?
C38 C39 C34 121.36(16) . . ?
C2 N1 C6 114.55(13) . . ?
C2 N1 Nb1 125.96(10) . . ?
C6 N1 Nb1 119.29(10) . . ?
C4 N2 C18 116.39(13) . . ?
C4 N2 Nb1 125.30(11) . . ?
C18 N2 Nb1 118.08(10) . . ?
C30 N3 Nb1 160.41(11) . . ?
N3 Nb1 F1 93.48(6) . . ?
N3 Nb1 N1 96.14(6) . . ?
F1 Nb1 N1 153.68(5) . . ?
N3 Nb1 C34 101.38(6) . . ?
F1 Nb1 C34 101.27(6) . . ?
N1 Nb1 C34 100.75(6) . . ?
N3 Nb1 N2 151.01(5) . . ?
F1 Nb1 N2 77.37(5) . . ?
N1 Nb1 N2 82.44(5) . . ?
C34 Nb1 N2 107.35(6) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.047
_database_code_depnum_ccdc_archive 'CCDC 977241'
#######################################################################
#
#                 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_(2)
_chemical_name_common            'Complex 2c'
_chemical_melting_point          ?
_chemical_formula_moiety         'C39 H53 F2 N3 Nb'
_chemical_formula_sum            'C39 H53 F2 N3 Nb'
_chemical_formula_weight         694.75

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'
Nb Nb -2.0727 0.6215 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.8194(10)
_cell_length_b                   12.3148(12)
_cell_length_c                   13.7249(13)
_cell_angle_alpha                79.695(6)
_cell_angle_beta                 87.396(6)
_cell_angle_gamma                88.376(6)
_cell_volume                     1797.0(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9987
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      25.39

_exptl_crystal_description       rode
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             734
_exptl_absorpt_coefficient_mu    0.375
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9458
_exptl_absorpt_correction_T_max  0.9706
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26452
_diffrn_reflns_av_R_equivalents  0.0659
_diffrn_reflns_av_sigmaI/netI    0.0798
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.51
_diffrn_reflns_theta_max         25.43
_reflns_number_total             6544
_reflns_number_gt                5065
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2 v.2011.4'
_computing_cell_refinement       'Bruker APEX2 v.2011.4'
_computing_data_reduction        'Bruker APEX2 v.2011.4'
_computing_structure_solution    SIR-2004
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ORTEP-32
_computing_publication_material  WinGX

_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)+(0.0231P)²+1.1305P] 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         6544
_refine_ls_number_parameters     429
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0445
_refine_ls_wR_factor_ref         0.0829
_refine_ls_wR_factor_gt          0.0746
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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
C1 C 0.2123(3) 0.0493(2) 0.8806(2) 0.0130(7) Uani 1 1 d . A .
C2 C 0.3318(3) 0.0186(3) 0.9084(2) 0.0228(8) Uani 1 1 d . . .
C3 C 0.3634(3) -0.0818(3) 0.9659(3) 0.0312(9) Uani 1 1 d . A .
H3 H 0.4470 -0.0999 0.9815 0.037 Uiso 1 1 calc R . .
C4 C 0.2696(4) -0.1552(3) 1.0002(3) 0.0344(10) Uani 1 1 d . . .
H4 H 0.2886 -0.2240 1.0409 0.041 Uiso 1 1 calc R A .
C5 C 0.1495(4) -0.1290(3) 0.9757(2) 0.0276(9) Uani 1 1 d . A .
H5 H 0.0855 -0.1795 0.9991 0.033 Uiso 1 1 calc R . .
C6 C 0.1221(3) -0.0290(3) 0.9170(2) 0.0192(8) Uani 1 1 d . . .
C7 C 0.5283(3) 0.2040(3) 0.6058(2) 0.0202(8) Uani 1 1 d . . .
H7A H 0.5216 0.1248 0.6059 0.030 Uiso 1 1 calc R . .
H7B H 0.6129 0.2201 0.6204 0.030 Uiso 1 1 calc R . .
H7C H 0.5080 0.2455 0.5404 0.030 Uiso 1 1 calc R . .
C8 C 0.4397(3) 0.2371(2) 0.6832(2) 0.0133(7) Uani 1 1 d . . .
C9 C 0.4899(3) 0.2870(2) 0.7542(2) 0.0149(7) Uani 1 1 d . . .
H9 H 0.5776 0.2836 0.7559 0.018 Uiso 1 1 calc R . .
C10 C 0.4289(3) 0.3424(2) 0.8247(2) 0.0151(7) Uani 1 1 d . . .
C11 C 0.5099(3) 0.4123(3) 0.8753(2) 0.0199(8) Uani 1 1 d . . .
H11A H 0.4689 0.4841 0.8766 0.030 Uiso 1 1 calc R . .
H11B H 0.5897 0.4233 0.8387 0.030 Uiso 1 1 calc R . .
H11C H 0.5232 0.3747 0.9433 0.030 Uiso 1 1 calc R . .
C12 C 0.2819(3) 0.1937(2) 0.5821(2) 0.0121(7) Uani 1 1 d . . .
C13 C 0.2688(3) 0.0836(2) 0.5702(2) 0.0147(7) Uani 1 1 d . . .
C14 C 0.2329(3) 0.0653(3) 0.4781(2) 0.0196(8) Uani 1 1 d . . .
H14 H 0.2223 -0.0083 0.4686 0.023 Uiso 1 1 calc R . .
C15 C 0.2124(3) 0.1508(3) 0.4008(2) 0.0219(8) Uani 1 1 d . . .
H15 H 0.1869 0.1360 0.3392 0.026 Uiso 1 1 calc R . .
C16 C 0.2291(3) 0.2582(3) 0.4131(2) 0.0181(8) Uani 1 1 d . . .
H16 H 0.2157 0.3170 0.3593 0.022 Uiso 1 1 calc R . .
C17 C 0.2653(3) 0.2821(2) 0.5029(2) 0.0137(7) Uani 1 1 d . . .
C18 C 0.2843(3) 0.4017(2) 0.5115(2) 0.0162(7) Uani 1 1 d . . .
H18 H 0.3246 0.4022 0.5756 0.019 Uiso 1 1 calc R . .
C19 C 0.1598(3) 0.4627(3) 0.5152(2) 0.0222(8) Uani 1 1 d . . .
H19A H 0.1148 0.4576 0.4559 0.033 Uiso 1 1 calc R . .
H19B H 0.1736 0.5405 0.5176 0.033 Uiso 1 1 calc R . .
H19C H 0.1112 0.4293 0.5744 0.033 Uiso 1 1 calc R . .
C20 C 0.3694(3) 0.4618(3) 0.4277(2) 0.0275(9) Uani 1 1 d . . .
H20A H 0.4474 0.4200 0.4248 0.041 Uiso 1 1 calc R . .
H20B H 0.3861 0.5357 0.4404 0.041 Uiso 1 1 calc R . .
H20C H 0.3288 0.4681 0.3645 0.041 Uiso 1 1 calc R . .
C21 C 0.2929(3) -0.0153(2) 0.6507(2) 0.0160(7) Uani 1 1 d . . .
H21 H 0.3214 0.0130 0.7096 0.019 Uiso 1 1 calc R . .
C22 C 0.1743(3) -0.0796(3) 0.6827(2) 0.0218(8) Uani 1 1 d . . .
H22A H 0.1090 -0.0291 0.7004 0.033 Uiso 1 1 calc R . .
H22B H 0.1901 -0.1373 0.7402 0.033 Uiso 1 1 calc R . .
H22C H 0.1481 -0.1137 0.6279 0.033 Uiso 1 1 calc R . .
C23 C 0.3946(3) -0.0920(3) 0.6197(2) 0.0270(9) Uani 1 1 d . . .
H23A H 0.3655 -0.1277 0.5668 0.041 Uiso 1 1 calc R . .
H23B H 0.4153 -0.1486 0.6768 0.041 Uiso 1 1 calc R . .
H23C H 0.4682 -0.0492 0.5955 0.041 Uiso 1 1 calc R . .
C24 C 0.2570(3) 0.4066(2) 0.9123(2) 0.0118(7) Uani 1 1 d . . .
C25 C 0.2646(3) 0.3726(2) 1.0153(2) 0.0147(7) Uani 1 1 d . . .
C26 C 0.2130(3) 0.4432(3) 1.0763(2) 0.0182(8) Uani 1 1 d . . .
H26 H 0.2174 0.4226 1.1462 0.022 Uiso 1 1 calc R . .
C27 C 0.1560(3) 0.5419(3) 1.0373(2) 0.0219(8) Uani 1 1 d . . .
H27 H 0.1227 0.5890 1.0801 0.026 Uiso 1 1 calc R . .
C28 C 0.1474(3) 0.5722(3) 0.9361(2) 0.0200(8) Uani 1 1 d . . .
H28 H 0.1067 0.6398 0.9099 0.024 Uiso 1 1 calc R . .
C29 C 0.1972(3) 0.5055(2) 0.8715(2) 0.0143(7) Uani 1 1 d . . .
C30 C 0.1855(3) 0.5395(2) 0.7601(2) 0.0172(7) Uani 1 1 d . . .
H30 H 0.1857 0.4701 0.7318 0.021 Uiso 1 1 calc R . .
C31 C 0.0653(3) 0.6019(3) 0.7314(2) 0.0261(8) Uani 1 1 d . . .
H31A H -0.0050 0.5592 0.7637 0.039 Uiso 1 1 calc R . .
H31B H 0.0585 0.6130 0.6593 0.039 Uiso 1 1 calc R . .
H31C H 0.0650 0.6738 0.7527 0.039 Uiso 1 1 calc R . .
C32 C 0.2979(3) 0.6053(3) 0.7134(3) 0.0303(9) Uani 1 1 d . . .
H32A H 0.3063 0.6699 0.7450 0.046 Uiso 1 1 calc R . .
H32B H 0.2867 0.6296 0.6423 0.046 Uiso 1 1 calc R . .
H32C H 0.3727 0.5585 0.7231 0.046 Uiso 1 1 calc R . .
C33 C 0.3189(3) 0.2610(3) 1.0616(2) 0.0189(8) Uani 1 1 d . . .
H33 H 0.3624 0.2283 1.0075 0.023 Uiso 1 1 calc R . .
C34 C 0.4140(3) 0.2691(3) 1.1403(2) 0.0283(9) Uani 1 1 d . . .
H34A H 0.3726 0.2971 1.1961 0.042 Uiso 1 1 calc R . .
H34B H 0.4794 0.3196 1.1109 0.042 Uiso 1 1 calc R . .
H34C H 0.4503 0.1958 1.1638 0.042 Uiso 1 1 calc R . .
C35 C 0.2145(3) 0.1831(3) 1.1065(2) 0.0269(9) Uani 1 1 d . . .
H35A H 0.1695 0.2138 1.1593 0.040 Uiso 1 1 calc R . .
H35B H 0.2500 0.1106 1.1341 0.040 Uiso 1 1 calc R . .
H35C H 0.1575 0.1752 1.0549 0.040 Uiso 1 1 calc R . .
C36 C -0.0688(3) 0.2004(2) 0.6827(2) 0.0137(7) Uani 1 1 d . . .
C37 C -0.1446(3) 0.1004(2) 0.7322(2) 0.0200(8) Uani 1 1 d . . .
H37A H -0.1016 0.0323 0.7210 0.030 Uiso 1 1 calc R . .
H37B H -0.2264 0.1049 0.7036 0.030 Uiso 1 1 calc R . .
H37C H -0.1543 0.1003 0.8036 0.030 Uiso 1 1 calc R . .
C38 C -0.0569(3) 0.2044(3) 0.5704(2) 0.0206(8) Uani 1 1 d . . .
H38A H -0.0076 0.2680 0.5397 0.031 Uiso 1 1 calc R . .
H38B H -0.1395 0.2116 0.5430 0.031 Uiso 1 1 calc R . .
H38C H -0.0162 0.1364 0.5566 0.031 Uiso 1 1 calc R . .
C39 C -0.1305(3) 0.3063(2) 0.7071(2) 0.0198(8) Uani 1 1 d . . .
H39A H -0.1396 0.3007 0.7792 0.030 Uiso 1 1 calc R . .
H39B H -0.2122 0.3164 0.6784 0.030 Uiso 1 1 calc R . .
H39C H -0.0791 0.3696 0.6793 0.030 Uiso 1 1 calc R . .
N1 N 0.3166(2) 0.21945(19) 0.67743(17) 0.0108(6) Uani 1 1 d . A .
N2 N 0.3082(2) 0.33601(19) 0.84544(17) 0.0112(6) Uani 1 1 d . A .
N3 N 0.0539(2) 0.18997(19) 0.72485(17) 0.0126(6) Uani 1 1 d . A .
F2 F 0.4225(3) 0.0772(3) 0.8778(2) 0.0236(11) Uani 0.532(4) 1 d P A 1
F2B F 0.0126(3) -0.0144(3) 0.8963(3) 0.0167(12) Uani 0.468(4) 1 d P A 2
F1 F 0.07554(15) 0.27874(14) 0.88813(12) 0.0198(4) Uani 1 1 d . A .
Nb1 Nb 0.17942(3) 0.21321(2) 0.79490(2) 0.01153(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 C2 1.387(4) . ?
C1 C6 1.404(4) . ?
C1 Nb1 2.176(3) . ?
C2 F2 1.246(4) . ?
C2 C3 1.386(5) . ?
C3 C4 1.387(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.373(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.377(4) . ?
C5 H5 0.9500 . ?
C6 F2B 1.231(4) . ?
C7 C8 1.501(4) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 N1 1.364(3) . ?
C8 C9 1.380(4) . ?
C9 C10 1.411(4) . ?
C9 H9 0.9500 . ?
C10 N2 1.325(4) . ?
C10 C11 1.518(4) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.405(4) . ?
C12 C17 1.408(4) . ?
C12 N1 1.468(3) . ?
C13 C14 1.397(4) . ?
C13 C21 1.517(4) . ?
C14 C15 1.375(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.382(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.392(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.519(4) . ?
C18 C19 1.527(4) . ?
C18 C20 1.535(4) . ?
C18 H18 1.0000 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C23 1.525(4) . ?
C21 C22 1.532(4) . ?
C21 H21 1.0000 . ?
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 C29 1.400(4) . ?
C24 C25 1.407(4) . ?
C24 N2 1.455(4) . ?
C25 C26 1.400(4) . ?
C25 C33 1.521(4) . ?
C26 C27 1.377(4) . ?
C26 H26 0.9500 . ?
C27 C28 1.380(4) . ?
C27 H27 0.9500 . ?
C28 C29 1.393(4) . ?
C28 H28 0.9500 . ?
C29 C30 1.522(4) . ?
C30 C31 1.523(4) . ?
C30 C32 1.532(4) . ?
C30 H30 1.0000 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 C35 1.537(4) . ?
C33 C34 1.542(4) . ?
C33 H33 1.0000 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C36 N3 1.465(3) . ?
C36 C39 1.531(4) . ?
C36 C38 1.533(4) . ?
C36 C37 1.536(4) . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?
N1 Nb1 2.134(2) . ?
N2 Nb1 2.301(2) . ?
N3 Nb1 1.758(2) . ?
F1 Nb1 1.9336(17) . ?

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
C2 C1 C6 114.9(3) . . ?
C2 C1 Nb1 118.7(2) . . ?
C6 C1 Nb1 126.2(2) . . ?
F2 C2 C3 113.6(3) . . ?
F2 C2 C1 122.2(3) . . ?
C3 C2 C1 124.0(3) . . ?
C2 C3 C4 118.2(3) . . ?
C2 C3 H3 120.9 . . ?
C4 C3 H3 120.9 . . ?
C5 C4 C3 120.4(3) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 119.7(3) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
F2B C6 C5 115.0(3) . . ?
F2B C6 C1 122.1(3) . . ?
C5 C6 C1 122.8(3) . . ?
C8 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C8 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C8 C9 124.5(3) . . ?
N1 C8 C7 118.8(2) . . ?
C9 C8 C7 116.6(3) . . ?
C8 C9 C10 128.9(3) . . ?
C8 C9 H9 115.5 . . ?
C10 C9 H9 115.5 . . ?
N2 C10 C9 122.9(3) . . ?
N2 C10 C11 121.3(3) . . ?
C9 C10 C11 115.8(3) . . ?
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 . . ?
C13 C12 C17 121.4(3) . . ?
C13 C12 N1 120.6(3) . . ?
C17 C12 N1 118.0(2) . . ?
C14 C13 C12 117.5(3) . . ?
C14 C13 C21 118.6(3) . . ?
C12 C13 C21 123.9(3) . . ?
C15 C14 C13 122.0(3) . . ?
C15 C14 H14 119.0 . . ?
C13 C14 H14 119.0 . . ?
C14 C15 C16 119.6(3) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C15 C16 C17 121.3(3) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 H16 119.4 . . ?
C16 C17 C12 118.2(3) . . ?
C16 C17 C18 118.9(3) . . ?
C12 C17 C18 123.0(3) . . ?
C17 C18 C19 110.4(2) . . ?
C17 C18 C20 112.5(3) . . ?
C19 C18 C20 110.6(3) . . ?
C17 C18 H18 107.7 . . ?
C19 C18 H18 107.7 . . ?
C20 C18 H18 107.7 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C13 C21 C23 112.3(3) . . ?
C13 C21 C22 111.2(2) . . ?
C23 C21 C22 110.2(2) . . ?
C13 C21 H21 107.6 . . ?
C23 C21 H21 107.6 . . ?
C22 C21 H21 107.6 . . ?
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 . . ?
C29 C24 C25 121.8(3) . . ?
C29 C24 N2 118.4(3) . . ?
C25 C24 N2 119.7(3) . . ?
C26 C25 C24 117.4(3) . . ?
C26 C25 C33 119.7(3) . . ?
C24 C25 C33 122.7(3) . . ?
C27 C26 C25 121.5(3) . . ?
C27 C26 H26 119.2 . . ?
C25 C26 H26 119.2 . . ?
C26 C27 C28 120.0(3) . . ?
C26 C27 H27 120.0 . . ?
C28 C27 H27 120.0 . . ?
C27 C28 C29 121.2(3) . . ?
C27 C28 H28 119.4 . . ?
C29 C28 H28 119.4 . . ?
C28 C29 C24 118.1(3) . . ?
C28 C29 C30 120.6(3) . . ?
C24 C29 C30 121.3(3) . . ?
C29 C30 C31 113.5(3) . . ?
C29 C30 C32 110.7(3) . . ?
C31 C30 C32 111.1(3) . . ?
C29 C30 H30 107.1 . . ?
C31 C30 H30 107.1 . . ?
C32 C30 H30 107.1 . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C30 C32 H32A 109.5 . . ?
C30 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C30 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C25 C33 C35 110.0(3) . . ?
C25 C33 C34 113.0(3) . . ?
C35 C33 C34 110.3(3) . . ?
C25 C33 H33 107.8 . . ?
C35 C33 H33 107.8 . . ?
C34 C33 H33 107.8 . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C33 C35 H35A 109.5 . . ?
C33 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C33 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
N3 C36 C39 107.6(2) . . ?
N3 C36 C38 110.2(2) . . ?
C39 C36 C38 111.0(3) . . ?
N3 C36 C37 108.2(2) . . ?
C39 C36 C37 109.5(2) . . ?
C38 C36 C37 110.2(2) . . ?
C36 C37 H37A 109.5 . . ?
C36 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C36 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C36 C38 H38A 109.5 . . ?
C36 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C36 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C36 C39 H39A 109.5 . . ?
C36 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C36 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C8 N1 C12 114.3(2) . . ?
C8 N1 Nb1 126.36(19) . . ?
C12 N1 Nb1 119.18(17) . . ?
C10 N2 C24 116.4(2) . . ?
C10 N2 Nb1 125.18(19) . . ?
C24 N2 Nb1 118.26(17) . . ?
C36 N3 Nb1 160.6(2) . . ?
N3 Nb1 F1 93.22(9) . . ?
N3 Nb1 N1 96.10(10) . . ?
F1 Nb1 N1 153.24(8) . . ?
N3 Nb1 C1 101.51(11) . . ?
F1 Nb1 C1 100.74(9) . . ?
N1 Nb1 C1 101.88(10) . . ?
N3 Nb1 N2 148.86(10) . . ?
F1 Nb1 N2 76.78(8) . . ?
N1 Nb1 N2 82.38(9) . . ?
C1 Nb1 N2 109.26(9) . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.756
_refine_diff_density_min         -0.469
_refine_diff_density_rms         0.090
_database_code_depnum_ccdc_archive 'CCDC 977242'
#######################################################################
#
#                 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_(3)

_chemical_name_common            'Complex 2d'
_chemical_melting_point          ?
_chemical_formula_moiety         'C39 H54 F2 N3 Nb'
_chemical_formula_sum            'C39 H54 F2 N3 Nb'
_chemical_formula_weight         695.76

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'
Nb Nb -2.0727 0.6215 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.9151(4)
_cell_length_b                   12.3010(4)
_cell_length_c                   13.7072(5)
_cell_angle_alpha                79.714(2)
_cell_angle_beta                 87.243(2)
_cell_angle_gamma                88.804(2)
_cell_volume                     1808.60(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9945
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      25.42

_exptl_crystal_description       rode
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             736
_exptl_absorpt_coefficient_mu    0.373
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9427
_exptl_absorpt_correction_T_max  0.9708
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(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  'Bruker APEX-I CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.366
_diffrn_reflns_number            42043
_diffrn_reflns_av_R_equivalents  0.0493
_diffrn_reflns_av_sigmaI/netI    0.0369
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.51
_diffrn_reflns_theta_max         25.47
_reflns_number_total             6684
_reflns_number_gt                5860
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2 v.2011.4'
_computing_cell_refinement       'Bruker APEX2 v.2011.4'
_computing_data_reduction        'Bruker APEX2 v.2011.4'
_computing_structure_solution    SIR-2004
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ORTEP-32
_computing_publication_material  WinGX

_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)+(0.0273P)²+1.2845P] 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         6684
_refine_ls_number_parameters     419
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0302
_refine_ls_wR_factor_ref         0.0702
_refine_ls_wR_factor_gt          0.0672
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_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
C1 C 0.2980(2) 0.44673(16) 0.12088(15) 0.0137(4) Uani 1 1 d . . .
C2 C 0.3912(2) 0.52291(16) 0.08767(16) 0.0168(5) Uani 1 1 d . . .
H2 H 0.4729 0.5046 0.1059 0.020 Uiso 1 1 calc R . .
C3 C 0.3671(2) 0.62469(17) 0.02861(17) 0.0216(5) Uani 1 1 d . . .
H3 H 0.4322 0.6742 0.0057 0.026 Uiso 1 1 calc R . .
C4 C 0.2486(2) 0.65349(17) 0.00344(17) 0.0211(5) Uani 1 1 d . . .
H4 H 0.2305 0.7233 -0.0356 0.025 Uiso 1 1 calc R . .
C5 C 0.1574(2) 0.57871(18) 0.03621(17) 0.0199(5) Uani 1 1 d . . .
C6 C 0.1785(2) 0.47640(17) 0.09273(16) 0.0169(5) Uani 1 1 d . . .
H6 H 0.1129 0.4265 0.1124 0.020 Uiso 1 1 calc R . .
C7 C -0.0244(2) 0.30054(18) 0.39056(17) 0.0199(5) Uani 1 1 d . . .
H7A H -0.0087 0.2559 0.4555 0.030 Uiso 1 1 calc R . .
H7B H -0.1086 0.2890 0.3733 0.030 Uiso 1 1 calc R . .
H7C H -0.0132 0.3788 0.3931 0.030 Uiso 1 1 calc R . .
C8 C 0.06425(19) 0.26650(16) 0.31299(15) 0.0133(4) Uani 1 1 d . . .
C9 C 0.0144(2) 0.22035(16) 0.23994(15) 0.0148(5) Uani 1 1 d . . .
H9 H -0.0720 0.2282 0.2356 0.018 Uiso 1 1 calc R . .
C10 C 0.0744(2) 0.16258(16) 0.16999(15) 0.0135(4) Uani 1 1 d . . .
C11 C -0.0084(2) 0.09621(18) 0.11844(17) 0.0212(5) Uani 1 1 d . . .
H11A H -0.0266 0.1385 0.0530 0.032 Uiso 1 1 calc R . .
H11B H -0.0850 0.0806 0.1583 0.032 Uiso 1 1 calc R . .
H11C H 0.0327 0.0265 0.1105 0.032 Uiso 1 1 calc R . .
C12 C 0.21979(19) 0.30536(16) 0.41723(15) 0.0130(4) Uani 1 1 d . . .
C13 C 0.2359(2) 0.21673(16) 0.49651(16) 0.0152(5) Uani 1 1 d . . .
C14 C 0.2712(2) 0.23998(18) 0.58665(16) 0.0212(5) Uani 1 1 d . . .
H14 H 0.2841 0.1809 0.6402 0.025 Uiso 1 1 calc R . .
C15 C 0.2881(2) 0.34740(19) 0.59992(17) 0.0240(5) Uani 1 1 d . . .
H15 H 0.3135 0.3617 0.6617 0.029 Uiso 1 1 calc R . .
C16 C 0.2676(2) 0.43363(18) 0.52291(16) 0.0209(5) Uani 1 1 d . . .
H16 H 0.2776 0.5073 0.5329 0.025 Uiso 1 1 calc R . .
C17 C 0.2327(2) 0.41523(16) 0.43072(16) 0.0162(5) Uani 1 1 d . . .
C18 C 0.2099(2) 0.51430(16) 0.35016(16) 0.0180(5) Uani 1 1 d . . .
H18 H 0.1818 0.4864 0.2909 0.022 Uiso 1 1 calc R . .
C19 C 0.3273(2) 0.57913(17) 0.31916(17) 0.0233(5) Uani 1 1 d . . .
H19A H 0.3538 0.6114 0.3749 0.035 Uiso 1 1 calc R . .
H19B H 0.3117 0.6383 0.2629 0.035 Uiso 1 1 calc R . .
H19C H 0.3916 0.5294 0.2998 0.035 Uiso 1 1 calc R . .
C20 C 0.1096(2) 0.59159(18) 0.38187(18) 0.0259(6) Uani 1 1 d . . .
H20A H 0.0358 0.5490 0.4056 0.039 Uiso 1 1 calc R . .
H20B H 0.0902 0.6488 0.3250 0.039 Uiso 1 1 calc R . .
H20C H 0.1387 0.6265 0.4353 0.039 Uiso 1 1 calc R . .
C21 C 0.2165(2) 0.09661(16) 0.48669(16) 0.0170(5) Uani 1 1 d . . .
H21 H 0.1770 0.0963 0.4224 0.020 Uiso 1 1 calc R . .
C22 C 0.1320(2) 0.03637(19) 0.57057(18) 0.0259(6) Uani 1 1 d . . .
H22A H 0.1729 0.0285 0.6336 0.039 Uiso 1 1 calc R . .
H22B H 0.1133 -0.0369 0.5570 0.039 Uiso 1 1 calc R . .
H22C H 0.0557 0.0790 0.5748 0.039 Uiso 1 1 calc R . .
C23 C 0.3399(2) 0.03635(17) 0.48361(18) 0.0216(5) Uani 1 1 d . . .
H23A H 0.3897 0.0714 0.4255 0.032 Uiso 1 1 calc R . .
H23B H 0.3265 -0.0411 0.4793 0.032 Uiso 1 1 calc R . .
H23C H 0.3829 0.0401 0.5441 0.032 Uiso 1 1 calc R . .
C24 C 0.24420(19) 0.09340(16) 0.08542(16) 0.0145(5) Uani 1 1 d . . .
C25 C 0.3018(2) -0.00572(16) 0.12730(17) 0.0168(5) Uani 1 1 d . . .
C26 C 0.3508(2) -0.07335(17) 0.06346(18) 0.0217(5) Uani 1 1 d . . .
H26 H 0.3885 -0.1417 0.0905 0.026 Uiso 1 1 calc R . .
C27 C 0.3457(2) -0.04345(18) -0.03801(18) 0.0240(5) Uani 1 1 d . . .
H27 H 0.3796 -0.0907 -0.0803 0.029 Uiso 1 1 calc R . .
C28 C 0.2910(2) 0.05545(18) -0.07779(17) 0.0211(5) Uani 1 1 d . . .
H28 H 0.2883 0.0759 -0.1478 0.025 Uiso 1 1 calc R . .
C29 C 0.2395(2) 0.12647(17) -0.01747(16) 0.0165(5) Uani 1 1 d . . .
C30 C 0.1883(2) 0.23861(18) -0.06551(16) 0.0190(5) Uani 1 1 d . . .
H30 H 0.1442 0.2719 -0.0122 0.023 Uiso 1 1 calc R . .
C31 C 0.2935(2) 0.31560(19) -0.10877(18) 0.0269(6) Uani 1 1 d . . .
H31A H 0.3478 0.3242 -0.0559 0.040 Uiso 1 1 calc R . .
H31B H 0.2599 0.3879 -0.1380 0.040 Uiso 1 1 calc R . .
H31C H 0.3400 0.2839 -0.1601 0.040 Uiso 1 1 calc R . .
C32 C 0.0965(2) 0.2304(2) -0.14476(18) 0.0290(6) Uani 1 1 d . . .
H32A H 0.1383 0.2014 -0.1998 0.044 Uiso 1 1 calc R . .
H32B H 0.0622 0.3038 -0.1695 0.044 Uiso 1 1 calc R . .
H32C H 0.0302 0.1806 -0.1158 0.044 Uiso 1 1 calc R . .
C33 C 0.3106(2) -0.03914(17) 0.23903(17) 0.0194(5) Uani 1 1 d . . .
H33 H 0.3104 0.0304 0.2673 0.023 Uiso 1 1 calc R . .
C34 C 0.1984(2) -0.1051(2) 0.28483(19) 0.0300(6) Uani 1 1 d . . .
H34A H 0.1244 -0.0592 0.2727 0.045 Uiso 1 1 calc R . .
H34B H 0.2071 -0.1272 0.3565 0.045 Uiso 1 1 calc R . .
H34C H 0.1919 -0.1711 0.2547 0.045 Uiso 1 1 calc R . .
C35 C 0.4295(2) -0.10223(19) 0.26884(19) 0.0264(6) Uani 1 1 d . . .
H35A H 0.4306 -0.1732 0.2458 0.040 Uiso 1 1 calc R . .
H35B H 0.4340 -0.1152 0.3412 0.040 Uiso 1 1 calc R . .
H35C H 0.5001 -0.0586 0.2385 0.040 Uiso 1 1 calc R . .
C36 C 0.57087(19) 0.29881(16) 0.31900(16) 0.0150(5) Uani 1 1 d . . .
C37 C 0.5585(2) 0.29479(19) 0.43135(16) 0.0222(5) Uani 1 1 d . . .
H37A H 0.5170 0.3622 0.4451 0.033 Uiso 1 1 calc R . .
H37B H 0.6402 0.2893 0.4586 0.033 Uiso 1 1 calc R . .
H37C H 0.5104 0.2303 0.4622 0.033 Uiso 1 1 calc R . .
C38 C 0.6346(2) 0.19434(17) 0.29394(17) 0.0202(5) Uani 1 1 d . . .
H38A H 0.5842 0.1299 0.3204 0.030 Uiso 1 1 calc R . .
H38B H 0.7149 0.1853 0.3237 0.030 Uiso 1 1 calc R . .
H38C H 0.6456 0.2011 0.2217 0.030 Uiso 1 1 calc R . .
C39 C 0.6436(2) 0.40109(17) 0.26858(17) 0.0202(5) Uani 1 1 d . . .
H39A H 0.6522 0.4017 0.1970 0.030 Uiso 1 1 calc R . .
H39B H 0.7251 0.3986 0.2960 0.030 Uiso 1 1 calc R . .
H39C H 0.5998 0.4681 0.2806 0.030 Uiso 1 1 calc R . .
N1 N 0.18685(16) 0.28055(13) 0.32157(12) 0.0111(4) Uani 1 1 d . . .
N2 N 0.19417(16) 0.16489(13) 0.15172(12) 0.0115(4) Uani 1 1 d . . .
N3 N 0.45048(16) 0.30715(13) 0.27663(13) 0.0128(4) Uani 1 1 d . . .
F1 F 0.42935(11) 0.21563(10) 0.11385(9) 0.0201(3) Uani 1 1 d . . .
F2 F 0.04038(13) 0.60871(11) 0.01145(12) 0.0348(4) Uani 1 1 d . . .
Nb1 Nb 0.325923(17) 0.282899(14) 0.206437(14) 0.01004(6) 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 C6 1.400(3) . ?
C1 C2 1.401(3) . ?
C1 Nb1 2.167(2) . ?
C2 C3 1.392(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.377(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.374(3) . ?
C4 H4 0.9500 . ?
C5 F2 1.363(3) . ?
C5 C6 1.376(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.511(3) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 N1 1.366(3) . ?
C8 C9 1.374(3) . ?
C9 C10 1.420(3) . ?
C9 H9 0.9500 . ?
C10 N2 1.319(3) . ?
C10 C11 1.510(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C17 1.407(3) . ?
C12 C13 1.410(3) . ?
C12 N1 1.461(3) . ?
C13 C14 1.391(3) . ?
C13 C21 1.527(3) . ?
C14 C15 1.383(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.379(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.395(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.517(3) . ?
C18 C19 1.525(3) . ?
C18 C20 1.533(3) . ?
C18 H18 1.0000 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C23 1.527(3) . ?
C21 C22 1.531(3) . ?
C21 H21 1.0000 . ?
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 C25 1.402(3) . ?
C24 C29 1.399(3) . ?
C24 N2 1.454(3) . ?
C25 C26 1.393(3) . ?
C25 C33 1.520(3) . ?
C26 C27 1.377(3) . ?
C26 H26 0.9500 . ?
C27 C28 1.377(3) . ?
C27 H27 0.9500 . ?
C28 C29 1.399(3) . ?
C28 H28 0.9500 . ?
C29 C30 1.525(3) . ?
C30 C31 1.531(3) . ?
C30 C32 1.531(3) . ?
C30 H30 1.0000 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 C34 1.529(3) . ?
C33 C35 1.533(3) . ?
C33 H33 1.0000 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C36 N3 1.456(3) . ?
C36 C37 1.531(3) . ?
C36 C38 1.533(3) . ?
C36 C39 1.539(3) . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?
N1 Nb1 2.1333(17) . ?
N2 Nb1 2.3061(16) . ?
N3 Nb1 1.7631(17) . ?
F1 Nb1 1.9411(12) . ?

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
C6 C1 C2 117.67(19) . . ?
C6 C1 Nb1 117.33(15) . . ?
C2 C1 Nb1 124.93(16) . . ?
C3 C2 C1 121.7(2) . . ?
C3 C2 H2 119.1 . . ?
C1 C2 H2 119.1 . . ?
C4 C3 C2 119.8(2) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C5 C4 C3 118.3(2) . . ?
C5 C4 H4 120.8 . . ?
C3 C4 H4 120.8 . . ?
F2 C5 C6 119.0(2) . . ?
F2 C5 C4 117.71(19) . . ?
C6 C5 C4 123.3(2) . . ?
C5 C6 C1 119.2(2) . . ?
C5 C6 H6 120.4 . . ?
C1 C6 H6 120.4 . . ?
C8 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C8 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C8 C9 124.80(19) . . ?
N1 C8 C7 118.46(18) . . ?
C9 C8 C7 116.71(19) . . ?
C8 C9 C10 128.9(2) . . ?
C8 C9 H9 115.5 . . ?
C10 C9 H9 115.5 . . ?
N2 C10 C9 122.83(19) . . ?
N2 C10 C11 121.84(19) . . ?
C9 C10 C11 115.32(19) . . ?
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 . . ?
C17 C12 C13 120.62(19) . . ?
C17 C12 N1 120.89(18) . . ?
C13 C12 N1 118.48(17) . . ?
C14 C13 C12 118.54(19) . . ?
C14 C13 C21 119.06(19) . . ?
C12 C13 C21 122.40(19) . . ?
C15 C14 C13 121.3(2) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C16 C15 C14 119.6(2) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C15 C16 C17 121.6(2) . . ?
C15 C16 H16 119.2 . . ?
C17 C16 H16 119.2 . . ?
C16 C17 C12 118.26(19) . . ?
C16 C17 C18 118.55(18) . . ?
C12 C17 C18 123.19(19) . . ?
C17 C18 C19 111.24(19) . . ?
C17 C18 C20 112.20(18) . . ?
C19 C18 C20 109.56(17) . . ?
C17 C18 H18 107.9 . . ?
C19 C18 H18 107.9 . . ?
C20 C18 H18 107.9 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C23 C21 C13 110.01(18) . . ?
C23 C21 C22 110.51(18) . . ?
C13 C21 C22 112.00(18) . . ?
C23 C21 H21 108.1 . . ?
C13 C21 H21 108.1 . . ?
C22 C21 H21 108.1 . . ?
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 . . ?
C25 C24 C29 121.56(19) . . ?
C25 C24 N2 118.22(18) . . ?
C29 C24 N2 120.14(18) . . ?
C26 C25 C24 118.0(2) . . ?
C26 C25 C33 120.70(19) . . ?
C24 C25 C33 121.28(18) . . ?
C27 C26 C25 121.5(2) . . ?
C27 C26 H26 119.2 . . ?
C25 C26 H26 119.2 . . ?
C28 C27 C26 119.6(2) . . ?
C28 C27 H27 120.2 . . ?
C26 C27 H27 120.2 . . ?
C27 C28 C29 121.6(2) . . ?
C27 C28 H28 119.2 . . ?
C29 C28 H28 119.2 . . ?
C28 C29 C24 117.7(2) . . ?
C28 C29 C30 119.3(2) . . ?
C24 C29 C30 122.81(19) . . ?
C29 C30 C31 110.04(19) . . ?
C29 C30 C32 113.00(18) . . ?
C31 C30 C32 110.71(19) . . ?
C29 C30 H30 107.6 . . ?
C31 C30 H30 107.6 . . ?
C32 C30 H30 107.6 . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C30 C32 H32A 109.5 . . ?
C30 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C30 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C25 C33 C34 110.93(19) . . ?
C25 C33 C35 113.05(19) . . ?
C34 C33 C35 110.92(18) . . ?
C25 C33 H33 107.2 . . ?
C34 C33 H33 107.2 . . ?
C35 C33 H33 107.2 . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C33 C35 H35A 109.5 . . ?
C33 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C33 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
N3 C36 C37 110.51(18) . . ?
N3 C36 C38 107.76(16) . . ?
C37 C36 C38 111.30(18) . . ?
N3 C36 C39 107.30(17) . . ?
C37 C36 C39 110.42(17) . . ?
C38 C36 C39 109.43(18) . . ?
C36 C37 H37A 109.5 . . ?
C36 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C36 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C36 C38 H38A 109.5 . . ?
C36 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C36 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C36 C39 H39A 109.5 . . ?
C36 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C36 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C8 N1 C12 114.61(17) . . ?
C8 N1 Nb1 126.07(14) . . ?
C12 N1 Nb1 119.10(13) . . ?
C10 N2 C24 116.77(17) . . ?
C10 N2 Nb1 124.95(13) . . ?
C24 N2 Nb1 118.09(12) . . ?
C36 N3 Nb1 161.29(14) . . ?
N3 Nb1 F1 93.19(7) . . ?
N3 Nb1 N1 96.90(7) . . ?
F1 Nb1 N1 153.80(6) . . ?
N3 Nb1 C1 100.46(8) . . ?
F1 Nb1 C1 100.96(7) . . ?
N1 Nb1 C1 100.89(7) . . ?
N3 Nb1 N2 151.27(7) . . ?
F1 Nb1 N2 77.00(5) . . ?
N1 Nb1 N2 82.66(6) . . ?
C1 Nb1 N2 107.86(7) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.469
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.065
_database_code_depnum_ccdc_archive 'CCDC 977243'
#######################################################################
#
#                 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_shelx

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            'Complex h'
_chemical_melting_point          ?
_chemical_formula_moiety         'C39 H52 F4 N3 Nb'
_chemical_formula_sum            'C39 H52 F4 N3 Nb'
_chemical_formula_weight         731.74

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'
Nb Nb -2.0727 0.6215 '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                   12.7898(5)
_cell_length_b                   11.5223(4)
_cell_length_c                   24.9612(9)
_cell_angle_alpha                90
_cell_angle_beta                 91.2170(10)
_cell_angle_gamma                90
_cell_volume                     3677.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9941
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      25.31

_exptl_crystal_description       rode
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_F_000             1536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.378
_shelx_estimated_absorpt_T_min   0.945
_shelx_estimated_absorpt_T_max   0.974
_exptl_absorpt_correction_type   multi_scan
_exptl_absorpt_correction_T_min  0.9717
_exptl_absorpt_correction_T_max  0.9802
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-I CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.366
_diffrn_reflns_number            26888
_diffrn_reflns_av_unetI/netI     0.0468
_diffrn_reflns_av_R_equivalents  0.0468
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.593
_diffrn_reflns_theta_max         25.357
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6733
_reflns_number_gt                5363
_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       'Bruker APEX2 v.2011.4'
_computing_cell_refinement       'Bruker APEX2 v.2011.4'
_computing_data_reduction        'Bruker APEX2 v.2011.4'
_computing_structure_solution    SIR-2004
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ORTEP-32
_computing_publication_material  WinGX

_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)+(0.0447P)²+2.5341P] 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         6733
_refine_ls_number_parameters     437
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0368
_refine_ls_wR_factor_ref         0.0929
_refine_ls_wR_factor_gt          0.0862
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.012
_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 0.7581(2) 0.0943(2) 0.11884(10) 0.0174(6) Uani 1 1 d . . . . .
C2 C 0.7821(2) -0.0020(2) 0.08900(11) 0.0198(6) Uani 1 1 d . . . . .
C3 C 0.7271(3) -0.1049(3) 0.09217(12) 0.0299(8) Uani 1 1 d . . . . .
C4 C 0.6438(3) -0.1163(3) 0.12542(13) 0.0375(9) Uani 1 1 d . . . . .
H4 H 0.6055 -0.1868 0.1266 0.045 Uiso 1 1 calc R U . . .
C5 C 0.6168(3) -0.0242(3) 0.15697(13) 0.0372(8) Uani 1 1 d . . . . .
H5 H 0.5601 -0.0291 0.1808 0.045 Uiso 1 1 calc R U . . .
C6 C 0.6754(2) 0.0760(3) 0.15265(11) 0.0238(7) Uani 1 1 d . . . . .
C7 C 0.8986(2) 0.6376(3) 0.17184(12) 0.0250(7) Uani 1 1 d . . . . .
H7A H 0.8472 0.7002 0.1677 0.037 Uiso 1 1 calc R U . . .
H7B H 0.9619 0.6577 0.1524 0.037 Uiso 1 1 calc R U . . .
H7C H 0.9163 0.6270 0.2099 0.037 Uiso 1 1 calc R U . . .
C8 C 0.8531(2) 0.5264(2) 0.14945(11) 0.0158(6) Uani 1 1 d . . . . .
C9 C 0.8007(2) 0.5364(2) 0.09941(11) 0.0174(6) Uani 1 1 d . . . . .
H9 H 0.8203 0.6017 0.0787 0.021 Uiso 1 1 calc R U . . .
C10 C 0.7247(2) 0.4654(2) 0.07559(10) 0.0153(6) Uani 1 1 d . . . . .
C11 C 0.6576(2) 0.5235(3) 0.03244(11) 0.0206(6) Uani 1 1 d . . . . .
H11A H 0.6250 0.5932 0.0472 0.031 Uiso 1 1 calc R U . . .
H11B H 0.6030 0.4696 0.0200 0.031 Uiso 1 1 calc R U . . .
H11C H 0.7014 0.5453 0.0023 0.031 Uiso 1 1 calc R U . . .
C12 C 0.9019(2) 0.4277(2) 0.23115(10) 0.0156(6) Uani 1 1 d . . . . .
C13 C 0.8332(2) 0.4227(2) 0.27388(11) 0.0181(6) Uani 1 1 d . . . . .
C14 C 0.8747(2) 0.4236(3) 0.32583(11) 0.0233(7) Uani 1 1 d . . . . .
H14 H 0.8288 0.4211 0.3552 0.028 Uiso 1 1 calc R U . . .
C15 C 0.9816(2) 0.4281(3) 0.33562(11) 0.0250(7) Uani 1 1 d . . . . .
H15 H 1.0086 0.4294 0.3714 0.030 Uiso 1 1 calc R U . . .
C16 C 1.0484(2) 0.4305(3) 0.29286(11) 0.0229(7) Uani 1 1 d . . . . .
H16 H 1.1218 0.4332 0.2996 0.028 Uiso 1 1 calc R U . . .
C17 C 1.0109(2) 0.4293(2) 0.24026(11) 0.0180(6) Uani 1 1 d . . . . .
C18 C 0.7153(2) 0.4196(3) 0.26531(11) 0.0207(6) Uani 1 1 d . . . . .
H18 H 0.7011 0.3891 0.2284 0.025 Uiso 1 1 calc R U . . .
C19 C 0.6700(3) 0.5414(3) 0.26777(15) 0.0389(9) Uani 1 1 d . . . . .
H19A H 0.6826 0.5738 0.3036 0.058 Uiso 1 1 calc R U . . .
H19B H 0.5946 0.5384 0.2601 0.058 Uiso 1 1 calc R U . . .
H19C H 0.7037 0.5906 0.2412 0.058 Uiso 1 1 calc R U . . .
C20 C 0.6620(2) 0.3377(3) 0.30454(12) 0.0304(8) Uani 1 1 d . . . . .
H20A H 0.6648 0.3715 0.3406 0.046 Uiso 1 1 calc R U . . .
H20B H 0.6981 0.2627 0.3049 0.046 Uiso 1 1 calc R U . . .
H20C H 0.5888 0.3264 0.2932 0.046 Uiso 1 1 calc R U . . .
C21 C 1.0891(2) 0.4271(3) 0.19521(11) 0.0242(7) Uani 1 1 d . . . . .
H21 H 1.0491 0.4326 0.1604 0.029 Uiso 1 1 calc R U . . .
C22 C 1.1662(2) 0.5286(3) 0.19801(13) 0.0375(9) Uani 1 1 d . . . . .
H22A H 1.1274 0.6017 0.2002 0.056 Uiso 1 1 calc R U . . .
H22B H 1.2087 0.5289 0.1658 0.056 Uiso 1 1 calc R U . . .
H22C H 1.2119 0.5201 0.2298 0.056 Uiso 1 1 calc R U . . .
C23 C 1.1479(2) 0.3116(3) 0.19594(12) 0.0316(8) Uani 1 1 d . . . . .
H23A H 1.1951 0.3085 0.1655 0.047 Uiso 1 1 calc R U . . .
H23B H 1.0977 0.2475 0.1933 0.047 Uiso 1 1 calc R U . . .
H23C H 1.1887 0.3047 0.2295 0.047 Uiso 1 1 calc R U . . .
C24 C 0.6079(2) 0.3033(2) 0.07339(10) 0.0157(6) Uani 1 1 d . . . . .
C25 C 0.6018(2) 0.2308(2) 0.02788(11) 0.0183(6) Uani 1 1 d . . . . .
C26 C 0.5046(2) 0.1862(3) 0.01275(12) 0.0253(7) Uani 1 1 d . . . . .
H26 H 0.4992 0.1366 -0.0176 0.030 Uiso 1 1 calc R U . . .
C27 C 0.4155(2) 0.2123(3) 0.04081(13) 0.0293(7) Uani 1 1 d . . . . .
H27 H 0.3497 0.1818 0.0294 0.035 Uiso 1 1 calc R U . . .
C28 C 0.4227(2) 0.2826(3) 0.08523(12) 0.0252(7) Uani 1 1 d . . . . .
H28 H 0.3614 0.2998 0.1045 0.030 Uiso 1 1 calc R U . . .
C29 C 0.5179(2) 0.3291(3) 0.10242(11) 0.0194(6) Uani 1 1 d . . . . .
C30 C 0.5182(2) 0.4076(3) 0.15167(11) 0.0228(7) Uani 1 1 d . . . . .
H30 H 0.5926 0.4208 0.1633 0.027 Uiso 1 1 calc R U . . .
C31 C 0.4611(2) 0.3519(3) 0.19837(12) 0.0329(8) Uani 1 1 d . . . . .
H31A H 0.4685 0.4014 0.2301 0.049 Uiso 1 1 calc R U . . .
H31B H 0.4915 0.2755 0.2061 0.049 Uiso 1 1 calc R U . . .
H31C H 0.3869 0.3432 0.1888 0.049 Uiso 1 1 calc R U . . .
C32 C 0.4690(3) 0.5259(3) 0.13868(14) 0.0376(8) Uani 1 1 d . . . . .
H32A H 0.4686 0.5736 0.1712 0.056 Uiso 1 1 calc R U . . .
H32B H 0.3971 0.5147 0.1254 0.056 Uiso 1 1 calc R U . . .
H32C H 0.5098 0.5649 0.1112 0.056 Uiso 1 1 calc R U . . .
C33 C 0.6963(2) 0.2032(2) -0.00639(11) 0.0204(6) Uani 1 1 d . . . . .
H33 H 0.7606 0.2098 0.0169 0.024 Uiso 1 1 calc R U . . .
C34 C 0.7062(3) 0.2892(3) -0.05272(12) 0.0286(7) Uani 1 1 d . . . . .
H34A H 0.7199 0.3670 -0.0384 0.043 Uiso 1 1 calc R U . . .
H34B H 0.6411 0.2900 -0.0741 0.043 Uiso 1 1 calc R U . . .
H34C H 0.7642 0.2657 -0.0754 0.043 Uiso 1 1 calc R U . . .
C35 C 0.6920(2) 0.0805(3) -0.02932(12) 0.0272(7) Uani 1 1 d . . . . .
H35A H 0.7603 0.0603 -0.0438 0.041 Uiso 1 1 calc R U . . .
H35B H 0.6385 0.0767 -0.0579 0.041 Uiso 1 1 calc R U . . .
H35C H 0.6746 0.0256 -0.0009 0.041 Uiso 1 1 calc R U . . .
C36 C 1.0187(2) 0.2662(3) 0.04464(11) 0.0215(6) Uani 1 1 d . . . . .
C37 C 1.0903(2) 0.1645(3) 0.05889(12) 0.0300(8) Uani 1 1 d . . . . .
H37A H 1.1492 0.1632 0.0345 0.045 Uiso 1 1 calc R U . . .
H37B H 1.0510 0.0918 0.0555 0.045 Uiso 1 1 calc R U . . .
H37C H 1.1166 0.1733 0.0958 0.045 Uiso 1 1 calc R U . . .
C38 C 1.0784(2) 0.3812(3) 0.04801(12) 0.0304(8) Uani 1 1 d . . . . .
H38A H 1.0294 0.4458 0.0426 0.046 Uiso 1 1 calc R U . . .
H38B H 1.1313 0.3833 0.0202 0.046 Uiso 1 1 calc R U . . .
H38C H 1.1126 0.3882 0.0834 0.046 Uiso 1 1 calc R U . . .
C39 C 0.9724(2) 0.2508(3) -0.01202(11) 0.0301(8) Uani 1 1 d . . . . .
H39A H 0.9258 0.3161 -0.0205 0.045 Uiso 1 1 calc R U . . .
H39B H 0.9327 0.1781 -0.0139 0.045 Uiso 1 1 calc R U . . .
H39C H 1.0290 0.2484 -0.0378 0.045 Uiso 1 1 calc R U . . .
N1 N 0.85980(16) 0.42676(19) 0.17648(8) 0.0134(5) Uani 1 1 d . . . . .
N2 N 0.70741(16) 0.35470(19) 0.09040(8) 0.0132(5) Uani 1 1 d . . . . .
N3 N 0.93323(17) 0.2693(2) 0.08247(9) 0.0172(5) Uani 1 1 d . . . . .
F1 F 0.90068(12) 0.19418(13) 0.19513(6) 0.0205(4) Uani 1 1 d . . . . .
F2 F 0.86248(13) 0.00131(14) 0.05428(6) 0.0259(4) Uani 1 1 d . . . . .
F3 F 0.75453(17) -0.19498(17) 0.06102(8) 0.0461(5) Uani 1 1 d . . . . .
F4 F 0.65134(13) 0.16790(16) 0.18558(7) 0.0324(4) Uani 1 1 d . . . . .
Nb1 Nb 0.83798(2) 0.26603(2) 0.13151(2) 0.01225(8) 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 C2 1.375(4) . ?
C1 C6 1.383(4) . ?
C1 Nb1 2.246(3) . ?
C2 F2 1.359(3) . ?
C2 C3 1.382(4) . ?
C3 F3 1.348(4) . ?
C3 C4 1.371(5) . ?
C4 C5 1.370(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.382(4) . ?
C5 H5 0.9500 . ?
C6 F4 1.379(3) . ?
C7 C8 1.509(4) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 N1 1.334(3) . ?
C8 C9 1.409(4) . ?
C9 C10 1.394(4) . ?
C9 H9 0.9500 . ?
C10 N2 1.348(3) . ?
C10 C11 1.518(4) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.397(4) . ?
C12 C17 1.407(4) . ?
C12 N1 1.457(3) . ?
C13 C14 1.391(4) . ?
C13 C18 1.519(4) . ?
C14 C15 1.384(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.382(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.389(4) . ?
C16 H16 0.9500 . ?
C17 C21 1.521(4) . ?
C18 C19 1.521(4) . ?
C18 C20 1.531(4) . ?
C18 H18 1.0000 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C23 1.529(4) . ?
C21 C22 1.531(4) . ?
C21 H21 1.0000 . ?
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 C29 1.406(4) . ?
C24 C25 1.411(4) . ?
C24 N2 1.458(3) . ?
C25 C26 1.390(4) . ?
C25 C33 1.528(4) . ?
C26 C27 1.383(4) . ?
C26 H26 0.9500 . ?
C27 C28 1.375(4) . ?
C27 H27 0.9500 . ?
C28 C29 1.389(4) . ?
C28 H28 0.9500 . ?
C29 C30 1.527(4) . ?
C30 C31 1.530(4) . ?
C30 C32 1.533(4) . ?
C30 H30 1.0000 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 C35 1.527(4) . ?
C33 C34 1.530(4) . ?
C33 H33 1.0000 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C36 N3 1.460(3) . ?
C36 C37 1.524(4) . ?
C36 C39 1.532(4) . ?
C36 C38 1.531(4) . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?
N1 Nb1 2.180(2) . ?
N2 Nb1 2.194(2) . ?
N3 Nb1 1.746(2) . ?
F1 Nb1 1.9482(15) . ?

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
C2 C1 C6 113.0(3) . . ?
C2 C1 Nb1 132.9(2) . . ?
C6 C1 Nb1 113.6(2) . . ?
F2 C2 C1 120.2(2) . . ?
F2 C2 C3 117.0(3) . . ?
C1 C2 C3 122.8(3) . . ?
F3 C3 C4 119.4(3) . . ?
F3 C3 C2 119.2(3) . . ?
C4 C3 C2 121.3(3) . . ?
C5 C4 C3 118.9(3) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 117.3(3) . . ?
C4 C5 H5 121.4 . . ?
C6 C5 H5 121.4 . . ?
F4 C6 C5 117.8(3) . . ?
F4 C6 C1 115.4(3) . . ?
C5 C6 C1 126.7(3) . . ?
C8 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C8 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C8 C9 122.9(2) . . ?
N1 C8 C7 121.5(2) . . ?
C9 C8 C7 115.6(2) . . ?
C10 C9 C8 130.1(3) . . ?
C10 C9 H9 114.9 . . ?
C8 C9 H9 114.9 . . ?
N2 C10 C9 123.7(2) . . ?
N2 C10 C11 121.2(2) . . ?
C9 C10 C11 115.0(2) . . ?
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 . . ?
C13 C12 C17 120.9(2) . . ?
C13 C12 N1 119.3(2) . . ?
C17 C12 N1 119.8(2) . . ?
C14 C13 C12 118.5(3) . . ?
C14 C13 C18 119.3(2) . . ?
C12 C13 C18 122.1(2) . . ?
C15 C14 C13 121.4(3) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C16 C15 C14 119.3(3) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
C15 C16 C17 121.5(3) . . ?
C15 C16 H16 119.2 . . ?
C17 C16 H16 119.2 . . ?
C16 C17 C12 118.3(3) . . ?
C16 C17 C21 118.7(2) . . ?
C12 C17 C21 123.0(2) . . ?
C13 C18 C19 110.5(2) . . ?
C13 C18 C20 112.3(2) . . ?
C19 C18 C20 111.6(3) . . ?
C13 C18 H18 107.4 . . ?
C19 C18 H18 107.4 . . ?
C20 C18 H18 107.4 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C17 C21 C23 109.7(2) . . ?
C17 C21 C22 112.8(3) . . ?
C23 C21 C22 110.4(2) . . ?
C17 C21 H21 108.0 . . ?
C23 C21 H21 108.0 . . ?
C22 C21 H21 108.0 . . ?
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 . . ?
C29 C24 C25 120.5(2) . . ?
C29 C24 N2 118.9(2) . . ?
C25 C24 N2 120.5(2) . . ?
C26 C25 C24 118.1(3) . . ?
C26 C25 C33 119.0(3) . . ?
C24 C25 C33 122.8(2) . . ?
C27 C26 C25 121.6(3) . . ?
C27 C26 H26 119.2 . . ?
C25 C26 H26 119.2 . . ?
C28 C27 C26 119.6(3) . . ?
C28 C27 H27 120.2 . . ?
C26 C27 H27 120.2 . . ?
C27 C28 C29 121.3(3) . . ?
C27 C28 H28 119.3 . . ?
C29 C28 H28 119.3 . . ?
C28 C29 C24 118.8(3) . . ?
C28 C29 C30 117.7(3) . . ?
C24 C29 C30 123.5(2) . . ?
C29 C30 C31 111.8(3) . . ?
C29 C30 C32 111.3(2) . . ?
C31 C30 C32 109.5(3) . . ?
C29 C30 H30 108.1 . . ?
C31 C30 H30 108.1 . . ?
C32 C30 H30 108.1 . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C30 C32 H32A 109.5 . . ?
C30 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C30 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C35 C33 C25 112.3(2) . . ?
C35 C33 C34 108.6(2) . . ?
C25 C33 C34 111.6(2) . . ?
C35 C33 H33 108.0 . . ?
C25 C33 H33 108.0 . . ?
C34 C33 H33 108.0 . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C33 C35 H35A 109.5 . . ?
C33 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C33 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
N3 C36 C37 108.8(2) . . ?
N3 C36 C39 108.7(2) . . ?
C37 C36 C39 110.2(2) . . ?
N3 C36 C38 108.8(2) . . ?
C37 C36 C38 110.9(2) . . ?
C39 C36 C38 109.5(2) . . ?
C36 C37 H37A 109.5 . . ?
C36 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C36 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C36 C38 H38A 109.5 . . ?
C36 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C36 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C36 C39 H39A 109.5 . . ?
C36 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C36 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C8 N1 C12 119.1(2) . . ?
C8 N1 Nb1 117.70(17) . . ?
C12 N1 Nb1 121.97(16) . . ?
C10 N2 C24 116.8(2) . . ?
C10 N2 Nb1 116.22(17) . . ?
C24 N2 Nb1 126.72(17) . . ?
C36 N3 Nb1 175.0(2) . . ?
N3 Nb1 F1 107.43(9) . . ?
N3 Nb1 N1 105.01(9) . . ?
F1 Nb1 N1 84.00(7) . . ?
N3 Nb1 N2 101.39(9) . . ?
F1 Nb1 N2 151.07(7) . . ?
N1 Nb1 N2 86.16(8) . . ?
N3 Nb1 C1 104.04(10) . . ?
F1 Nb1 C1 85.33(8) . . ?
N1 Nb1 C1 150.87(9) . . ?
N2 Nb1 C1 90.27(9) . . ?

_refine_diff_density_max         0.963
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.072

_shelxl_version_number           2014-1

_database_code_depnum_ccdc_archive 'CCDC 994967'
