# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2013

#######################################################################
#
#                 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.
#
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#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
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#  from this site to visualise CIF-encoded structures and 
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data_3

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H44 N5 Nb'
_chemical_formula_weight         483.54

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   35.1793(19)
_cell_length_b                   9.4430(6)
_cell_length_c                   16.9347(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.2820(10)
_cell_angle_gamma                90.00
_cell_volume                     5371.7(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    260(2)
_cell_measurement_reflns_used    2756
_cell_measurement_theta_min      2.2403
_cell_measurement_theta_max      22.6531

_exptl_crystal_description       Prismatic
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.196
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2064
_exptl_absorpt_coefficient_mu    0.465
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6020
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      260(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21659
_diffrn_reflns_av_R_equivalents  0.0564
_diffrn_reflns_av_sigmaI/netI    0.0858
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       49
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.45
_diffrn_reflns_theta_max         30.54
_reflns_number_total             8144
_reflns_number_gt                4844
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'


_refine_special_details          
; 
 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F^2^, conventional R-factors R are based 
 on F, with F set to zero for negative F^2^. The threshold expression of 
 F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F^2^ 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/[\s^2^(Fo^2^)+(0.0387P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     patterson
_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         8144
_refine_ls_number_parameters     275
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0999
_refine_ls_R_factor_gt           0.0465
_refine_ls_wR_factor_ref         0.1020
_refine_ls_wR_factor_gt          0.0852
_refine_ls_goodness_of_fit_ref   0.954
_refine_ls_restrained_S_all      0.954
_refine_ls_shift/su_max          0.002
_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
Nb1 Nb 0.654939(7) 0.90879(2) 0.963448(14) 0.03127(8) Uani 1 1 d . . .
N1 N 0.63041(6) 0.7919(2) 1.01512(13) 0.0356(5) Uani 1 1 d . . .
N2 N 0.61592(7) 1.0731(2) 0.90195(14) 0.0385(5) Uani 1 1 d . . .
N3 N 0.60051(8) 0.9698(3) 0.76368(15) 0.0545(7) Uani 1 1 d . . .
N4 N 0.69038(7) 0.7821(3) 0.92134(15) 0.0491(6) Uani 1 1 d . . .
N5 N 0.69244(6) 1.0333(3) 1.04718(15) 0.0441(6) Uani 1 1 d . . .
C1 C 0.60969(7) 0.7045(3) 1.05379(16) 0.0343(6) Uani 1 1 d . . .
C2 C 0.56765(8) 0.6948(3) 1.02305(18) 0.0415(7) Uani 1 1 d . . .
C3 C 0.54825(9) 0.6102(3) 1.0652(2) 0.0551(9) Uani 1 1 d . . .
H3 H 0.5206 0.6040 1.0458 0.066 Uiso 1 1 calc R . .
C4 C 0.56801(10) 0.5347(3) 1.1346(2) 0.0575(9) Uani 1 1 d . . .
H4 H 0.5540 0.4785 1.1615 0.069 Uiso 1 1 calc R . .
C5 C 0.60869(10) 0.5434(3) 1.16348(19) 0.0510(8) Uani 1 1 d . . .
H5 H 0.6221 0.4921 1.2104 0.061 Uiso 1 1 calc R . .
C6 C 0.63042(8) 0.6266(3) 1.12471(17) 0.0384(6) Uani 1 1 d . . .
C7 C 0.54611(8) 0.7748(3) 0.9463(2) 0.0549(9) Uani 1 1 d . . .
H7 H 0.5608 0.8630 0.9465 0.066 Uiso 1 1 calc R . .
C8 C 0.54651(11) 0.6929(4) 0.8690(2) 0.0850(12) Uani 1 1 d . . .
H8A H 0.5735 0.6710 0.8714 0.102 Uiso 1 1 calc R . .
H8B H 0.5346 0.7494 0.8209 0.102 Uiso 1 1 calc R . .
H8C H 0.5317 0.6066 0.8660 0.102 Uiso 1 1 calc R . .
C9 C 0.50354(9) 0.8158(4) 0.9417(3) 0.0949(15) Uani 1 1 d . . .
H9A H 0.4882 0.7317 0.9414 0.114 Uiso 1 1 calc R . .
H9B H 0.4919 0.8688 0.8920 0.114 Uiso 1 1 calc R . .
H9C H 0.5038 0.8726 0.9888 0.114 Uiso 1 1 calc R . .
C10 C 0.67518(8) 0.6344(3) 1.15946(18) 0.0475(7) Uani 1 1 d . . .
H10 H 0.6850 0.6961 1.1232 0.057 Uiso 1 1 calc R . .
C11 C 0.69424(10) 0.4894(4) 1.1603(2) 0.0754(11) Uani 1 1 d . . .
H11A H 0.6852 0.4268 1.1956 0.090 Uiso 1 1 calc R . .
H11B H 0.7227 0.4983 1.1807 0.090 Uiso 1 1 calc R . .
H11C H 0.6869 0.4517 1.1052 0.090 Uiso 1 1 calc R . .
C12 C 0.68775(10) 0.6997(4) 1.24586(19) 0.0687(10) Uani 1 1 d . . .
H12A H 0.6816 0.6352 1.2842 0.082 Uiso 1 1 calc R . .
H12B H 0.6737 0.7870 1.2452 0.082 Uiso 1 1 calc R . .
H12C H 0.7159 0.7178 1.2625 0.082 Uiso 1 1 calc R . .
C13 C 0.61651(8) 0.9811(3) 0.84586(16) 0.0386(6) Uani 1 1 d . . .
C14 C 0.60792(12) 0.8385(4) 0.7251(2) 0.0788(11) Uani 1 1 d . . .
H14A H 0.6232 0.7753 0.7669 0.095 Uiso 1 1 calc R . .
H14B H 0.6224 0.8591 0.6865 0.095 Uiso 1 1 calc R . .
H14C H 0.5830 0.7948 0.6965 0.095 Uiso 1 1 calc R . .
C15 C 0.57945(11) 1.0772(4) 0.7064(2) 0.0774(12) Uani 1 1 d . . .
H15A H 0.5514 1.0583 0.6909 0.093 Uiso 1 1 calc R . .
H15B H 0.5883 1.0760 0.6580 0.093 Uiso 1 1 calc R . .
H15C H 0.5847 1.1685 0.7322 0.093 Uiso 1 1 calc R . .
C16 C 0.59429(9) 1.2041(3) 0.91092(19) 0.0493(8) Uani 1 1 d . . .
C17 C 0.54959(10) 1.1917(4) 0.8662(2) 0.0831(12) Uani 1 1 d . . .
H17A H 0.5453 1.1908 0.8076 0.100 Uiso 1 1 calc R . .
H17B H 0.5359 1.2711 0.8806 0.100 Uiso 1 1 calc R . .
H17C H 0.5396 1.1056 0.8826 0.100 Uiso 1 1 calc R . .
C18 C 0.61253(12) 1.3313(3) 0.8810(3) 0.0828(12) Uani 1 1 d . . .
H18A H 0.6407 1.3326 0.9077 0.099 Uiso 1 1 calc R . .
H18B H 0.6009 1.4166 0.8944 0.099 Uiso 1 1 calc R . .
H18C H 0.6075 1.3253 0.8222 0.099 Uiso 1 1 calc R . .
C19 C 0.60035(11) 1.2194(4) 1.0028(2) 0.0754(11) Uani 1 1 d . . .
H19A H 0.5899 1.1374 1.0228 0.091 Uiso 1 1 calc R . .
H19B H 0.5867 1.3024 1.0128 0.091 Uiso 1 1 calc R . .
H19C H 0.6283 1.2280 1.0312 0.091 Uiso 1 1 calc R . .
C20 C 0.69438(12) 0.6309(4) 0.9293(3) 0.0900(14) Uani 1 1 d . . .
H20A H 0.6831 0.5876 0.8762 0.108 Uiso 1 1 calc R . .
H20B H 0.6807 0.5976 0.9670 0.108 Uiso 1 1 calc R . .
H20C H 0.7221 0.6065 0.9501 0.108 Uiso 1 1 calc R . .
C21 C 0.71267(12) 0.8355(5) 0.8688(3) 0.1005(15) Uani 1 1 d . . .
H21A H 0.7404 0.8149 0.8931 0.121 Uiso 1 1 calc R . .
H21B H 0.7090 0.9361 0.8627 0.121 Uiso 1 1 calc R . .
H21C H 0.7034 0.7912 0.8155 0.121 Uiso 1 1 calc R . .
C22 C 0.70244(11) 1.0346(4) 1.1357(2) 0.0764(11) Uani 1 1 d . . .
H22A H 0.7299 1.0086 1.1591 0.092 Uiso 1 1 calc R . .
H22B H 0.6859 0.9682 1.1532 0.092 Uiso 1 1 calc R . .
H22C H 0.6982 1.1278 1.1541 0.092 Uiso 1 1 calc R . .
C23 C 0.71347(10) 1.1421(4) 1.0178(2) 0.0714(10) Uani 1 1 d . . .
H23A H 0.7048 1.2334 1.0307 0.086 Uiso 1 1 calc R . .
H23B H 0.7081 1.1335 0.9591 0.086 Uiso 1 1 calc R . .
H23C H 0.7415 1.1321 1.0442 0.086 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Nb1 0.03263(12) 0.03206(13) 0.02877(12) 0.00090(12) 0.00857(9) -0.00218(11)
N1 0.0325(11) 0.0369(13) 0.0343(12) 0.0029(10) 0.0052(10) -0.0016(10)
N2 0.0446(13) 0.0382(14) 0.0330(12) 0.0029(10) 0.0121(10) 0.0008(11)
N3 0.0731(17) 0.0526(16) 0.0304(14) 0.0016(12) 0.0041(13) 0.0018(14)
N4 0.0486(14) 0.0522(16) 0.0490(15) -0.0065(12) 0.0184(12) 0.0042(12)
N5 0.0414(13) 0.0442(14) 0.0430(14) -0.0017(12) 0.0069(11) -0.0081(11)
C1 0.0374(14) 0.0268(13) 0.0406(15) -0.0040(12) 0.0144(12) -0.0036(11)
C2 0.0357(14) 0.0356(16) 0.0530(18) -0.0080(13) 0.0132(13) -0.0045(12)
C3 0.0400(16) 0.051(2) 0.080(2) -0.0139(18) 0.0254(17) -0.0163(14)
C4 0.068(2) 0.051(2) 0.064(2) -0.0027(17) 0.0359(19) -0.0196(17)
C5 0.070(2) 0.0417(17) 0.0456(18) 0.0039(14) 0.0230(16) -0.0119(15)
C6 0.0444(15) 0.0344(15) 0.0382(15) 0.0010(12) 0.0154(13) -0.0051(12)
C7 0.0321(15) 0.0471(19) 0.078(2) 0.0008(17) 0.0047(15) -0.0054(14)
C8 0.081(3) 0.093(3) 0.062(3) 0.008(2) -0.008(2) 0.010(2)
C9 0.044(2) 0.075(3) 0.152(4) 0.016(3) 0.007(2) 0.0099(19)
C10 0.0460(16) 0.0507(18) 0.0443(17) 0.0164(14) 0.0114(14) 0.0007(14)
C11 0.065(2) 0.071(3) 0.091(3) 0.021(2) 0.024(2) 0.016(2)
C12 0.064(2) 0.080(3) 0.052(2) 0.0107(19) 0.0017(17) -0.0100(19)
C13 0.0438(15) 0.0382(16) 0.0322(15) 0.0022(12) 0.0087(12) -0.0040(13)
C14 0.101(3) 0.084(3) 0.044(2) -0.022(2) 0.010(2) 0.005(2)
C15 0.106(3) 0.068(2) 0.0423(19) 0.0120(18) -0.0036(19) -0.010(2)
C16 0.0603(19) 0.0395(17) 0.0514(19) 0.0052(14) 0.0213(16) 0.0107(15)
C17 0.064(2) 0.085(3) 0.097(3) 0.015(2) 0.019(2) 0.026(2)
C18 0.113(3) 0.043(2) 0.101(3) 0.010(2) 0.045(3) 0.014(2)
C19 0.093(3) 0.078(3) 0.063(2) -0.008(2) 0.035(2) 0.027(2)
C20 0.121(4) 0.070(3) 0.088(3) -0.001(2) 0.045(3) 0.034(3)
C21 0.102(3) 0.099(3) 0.134(4) -0.014(3) 0.086(3) 0.001(3)
C22 0.096(3) 0.072(2) 0.049(2) -0.0088(19) 0.003(2) -0.014(2)
C23 0.065(2) 0.063(2) 0.090(3) -0.008(2) 0.028(2) -0.0203(19)

_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
Nb1 N1 1.783(2) . ?
Nb1 N5 2.005(2) . ?
Nb1 N4 2.005(2) . ?
Nb1 N2 2.128(2) . ?
Nb1 C13 2.159(3) . ?
N1 C1 1.387(3) . ?
N2 C13 1.292(3) . ?
N2 C16 1.484(3) . ?
N3 C13 1.341(3) . ?
N3 C15 1.446(4) . ?
N3 C14 1.460(4) . ?
N4 C20 1.438(4) . ?
N4 C21 1.441(4) . ?
N5 C22 1.435(4) . ?
N5 C23 1.438(4) . ?
C1 C6 1.412(4) . ?
C1 C2 1.418(3) . ?
C2 C3 1.380(4) . ?
C2 C7 1.500(4) . ?
C3 C4 1.374(4) . ?
C4 C5 1.371(4) . ?
C5 C6 1.390(4) . ?
C6 C10 1.510(4) . ?
C7 C8 1.524(5) . ?
C7 C9 1.526(4) . ?
C10 C11 1.523(4) . ?
C10 C12 1.527(4) . ?
C16 C19 1.513(4) . ?
C16 C18 1.518(4) . ?
C16 C17 1.534(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
N1 Nb1 N5 109.18(10) . . ?
N1 Nb1 N4 104.36(10) . . ?
N5 Nb1 N4 104.66(10) . . ?
N1 Nb1 N2 110.85(9) . . ?
N5 Nb1 N2 96.42(9) . . ?
N4 Nb1 N2 129.77(10) . . ?
N1 Nb1 C13 112.75(10) . . ?
N5 Nb1 C13 124.56(11) . . ?
N4 Nb1 C13 98.38(10) . . ?
N2 Nb1 C13 35.09(9) . . ?
C1 N1 Nb1 177.33(18) . . ?
C13 N2 C16 139.2(2) . . ?
C13 N2 Nb1 73.76(15) . . ?
C16 N2 Nb1 146.50(18) . . ?
C13 N3 C15 127.9(3) . . ?
C13 N3 C14 117.1(3) . . ?
C15 N3 C14 114.8(3) . . ?
C20 N4 C21 110.5(3) . . ?
C20 N4 Nb1 127.8(2) . . ?
C21 N4 Nb1 121.4(2) . . ?
C22 N5 C23 111.3(3) . . ?
C22 N5 Nb1 130.5(2) . . ?
C23 N5 Nb1 118.2(2) . . ?
N1 C1 C6 120.0(2) . . ?
N1 C1 C2 120.1(2) . . ?
C6 C1 C2 119.8(2) . . ?
C3 C2 C1 118.0(3) . . ?
C3 C2 C7 122.7(3) . . ?
C1 C2 C7 119.3(3) . . ?
C4 C3 C2 122.7(3) . . ?
C5 C4 C3 118.9(3) . . ?
C4 C5 C6 121.9(3) . . ?
C5 C6 C1 118.6(3) . . ?
C5 C6 C10 120.0(3) . . ?
C1 C6 C10 121.4(2) . . ?
C2 C7 C8 110.9(3) . . ?
C2 C7 C9 114.0(3) . . ?
C8 C7 C9 110.1(3) . . ?
C6 C10 C11 111.4(3) . . ?
C6 C10 C12 111.4(3) . . ?
C11 C10 C12 110.6(3) . . ?
N2 C13 N3 136.3(3) . . ?
N2 C13 Nb1 71.15(15) . . ?
N3 C13 Nb1 152.5(2) . . ?
N2 C16 C19 105.4(2) . . ?
N2 C16 C18 110.2(3) . . ?
C19 C16 C18 108.8(3) . . ?
N2 C16 C17 111.6(3) . . ?
C19 C16 C17 109.0(3) . . ?
C18 C16 C17 111.7(3) . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        30.54
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.380
_refine_diff_density_min         -0.578
_refine_diff_density_rms         0.074

#=======================================================================_eof


# End of Crystallographic Information File
_database_code_depnum_ccdc_archive 'CCDC 948135'