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


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#                                CCDC 
# 
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# 
#  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 
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data_1a
_database_code_depnum_ccdc_archive 'CCDC 924356'
#TrackingRef 'xray.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C31 H42 Br N4 Nb'
_chemical_formula_weight         643.51
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'
Br Br -0.2901 2.4595 '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   P2(1)/c
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
_cell_length_a                   11.9922(14)
_cell_length_b                   18.927(2)
_cell_length_c                   15.0340(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.5790(10)
_cell_angle_gamma                90.00
_cell_volume                     3150.7(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    260(2)
_cell_measurement_reflns_used    4935
_cell_measurement_theta_min      2.6049
_cell_measurement_theta_max      22.1105
_exptl_crystal_description       Prismatic
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.352
_exptl_crystal_size_mid          0.173
_exptl_crystal_size_min          0.142
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1328
_exptl_absorpt_coefficient_mu    1.675
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6440
_exptl_absorpt_correction_T_max  0.7458
_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 scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20346
_diffrn_reflns_av_R_equivalents  0.0913
_diffrn_reflns_av_unetI/netI     0.0752
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.82
_diffrn_reflns_theta_max         25.00
_reflns_number_total             5509
_reflns_number_gt                3840
_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^)+(0.0193P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5509
_refine_ls_number_parameters     345
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.0348
_refine_ls_wR_factor_ref         0.0708
_refine_ls_wR_factor_gt          0.0672
_refine_ls_goodness_of_fit_ref   0.873
_refine_ls_restrained_S_all      0.873
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Nb1 Nb 0.14122(2) 1.019434(14) 0.76273(2) 0.03648(9) Uani 1 1 d . . .
Br1 Br -0.44781(3) 1.219144(18) 0.74569(4) 0.07691(16) Uani 1 1 d . . .
N1 N 0.28503(18) 1.00062(12) 0.76231(18) 0.0387(6) Uani 1 1 d . . .
N2 N 0.02736(19) 0.94756(13) 0.66208(19) 0.0401(6) Uani 1 1 d . . .
N3 N -0.1821(2) 0.92750(16) 0.6202(2) 0.0547(8) Uani 1 1 d . . .
H3 H -0.176(3) 0.8932(15) 0.581(2) 0.058(11) Uiso 1 1 d . . .
N4 N -0.06572(19) 1.01131(12) 0.73752(19) 0.0397(6) Uani 1 1 d . . .
C1 C 0.4055(3) 0.98747(16) 0.7611(3) 0.0468(9) Uani 1 1 d . . .
C2 C 0.5001(2) 1.01613(18) 0.8545(3) 0.0621(10) Uani 1 1 d . . .
H2A H 0.4909 1.0664 0.8571 0.093 Uiso 1 1 calc R . .
H2B H 0.5794 1.0056 0.8566 0.093 Uiso 1 1 calc R . .
H2C H 0.4896 0.9945 0.9085 0.093 Uiso 1 1 calc R . .
C3 C 0.4133(3) 1.02633(17) 0.6745(3) 0.0645(11) Uani 1 1 d . . .
H3C H 0.3540 1.0075 0.6162 0.097 Uiso 1 1 calc R . .
H3D H 0.4924 1.0201 0.6739 0.097 Uiso 1 1 calc R . .
H3E H 0.3983 1.0758 0.6791 0.097 Uiso 1 1 calc R . .
C4 C 0.4249(3) 0.90829(16) 0.7533(3) 0.0613(11) Uani 1 1 d . . .
H4A H 0.4131 0.8840 0.8051 0.092 Uiso 1 1 calc R . .
H4B H 0.5055 0.9001 0.7570 0.092 Uiso 1 1 calc R . .
H4C H 0.3680 0.8910 0.6928 0.092 Uiso 1 1 calc R . .
C5 C -0.0777(2) 0.96143(16) 0.6721(2) 0.0406(8) Uani 1 1 d . . .
C6 C 0.0436(3) 0.88782(17) 0.6052(2) 0.0478(9) Uani 1 1 d . . .
H6 H -0.0364 0.8719 0.5615 0.057 Uiso 1 1 calc R . .
C7 C 0.1054(3) 0.82697(17) 0.6709(3) 0.0683(11) Uani 1 1 d . . .
H7A H 0.1825 0.8422 0.7165 0.102 Uiso 1 1 calc R . .
H7B H 0.1166 0.7887 0.6332 0.102 Uiso 1 1 calc R . .
H7C H 0.0562 0.8113 0.7046 0.102 Uiso 1 1 calc R . .
C8 C 0.1126(3) 0.91241(18) 0.5449(3) 0.0623(10) Uani 1 1 d . . .
H8A H 0.0640 0.9453 0.4970 0.094 Uiso 1 1 calc R . .
H8B H 0.1313 0.8725 0.5138 0.094 Uiso 1 1 calc R . .
H8C H 0.1861 0.9351 0.5856 0.094 Uiso 1 1 calc R . .
C9 C -0.2808(2) 0.91176(17) 0.6533(3) 0.0493(9) Uani 1 1 d . . .
H9 H -0.2983 0.9543 0.6829 0.059 Uiso 1 1 calc R . .
C10 C -0.3914(3) 0.8922(2) 0.5664(3) 0.0880(14) Uani 1 1 d . . .
H10A H -0.4170 0.9321 0.5240 0.132 Uiso 1 1 calc R . .
H10B H -0.4550 0.8784 0.5867 0.132 Uiso 1 1 calc R . .
H10C H -0.3725 0.8535 0.5333 0.132 Uiso 1 1 calc R . .
C11 C -0.2461(3) 0.8533(2) 0.7259(3) 0.0843(13) Uani 1 1 d . . .
H11A H -0.2242 0.8122 0.6988 0.127 Uiso 1 1 calc R . .
H11B H -0.3132 0.8421 0.7433 0.127 Uiso 1 1 calc R . .
H11C H -0.1787 0.8679 0.7822 0.127 Uiso 1 1 calc R . .
C12 C 0.1200(3) 1.12661(16) 0.6998(3) 0.0563(10) Uani 1 1 d . . .
H12A H 0.1703 1.1356 0.6635 0.068 Uiso 1 1 calc R . .
H12B H 0.0368 1.1401 0.6633 0.068 Uiso 1 1 calc R . .
C13 C 0.1694(3) 1.15434(15) 0.7981(3) 0.0470(9) Uani 1 1 d . . .
C14 C 0.0956(3) 1.16918(17) 0.8476(3) 0.0657(11) Uani 1 1 d . . .
H14 H 0.0123 1.1661 0.8148 0.079 Uiso 1 1 calc R . .
C15 C 0.1395(4) 1.1880(2) 0.9421(4) 0.0891(14) Uani 1 1 d . . .
H15 H 0.0866 1.1983 0.9721 0.107 Uiso 1 1 calc R . .
C16 C 0.2618(5) 1.1919(2) 0.9932(4) 0.0975(15) Uani 1 1 d . . .
H16 H 0.2923 1.2037 1.0582 0.117 Uiso 1 1 calc R . .
C17 C 0.3381(4) 1.1784(2) 0.9475(4) 0.0891(15) Uani 1 1 d . . .
H17 H 0.4211 1.1818 0.9813 0.107 Uiso 1 1 calc R . .
C18 C 0.2935(3) 1.15971(18) 0.8518(3) 0.0659(11) Uani 1 1 d . . .
H18 H 0.3472 1.1504 0.8221 0.079 Uiso 1 1 calc R . .
C21 C 0.1862(3) 0.99986(14) 0.9183(2) 0.0431(8) Uani 1 1 d . . .
H21A H 0.2654 1.0184 0.9571 0.052 Uiso 1 1 calc R . .
H21B H 0.1267 1.0211 0.9391 0.052 Uiso 1 1 calc R . .
C22 C 0.1840(2) 0.92225(16) 0.9247(2) 0.0406(8) Uani 1 1 d . . .
C23 C 0.2861(3) 0.88071(16) 0.9385(2) 0.0459(8) Uani 1 1 d . . .
H23 H 0.3589 0.9030 0.9478 0.055 Uiso 1 1 calc R . .
C24 C 0.2825(3) 0.80848(17) 0.9387(3) 0.0583(10) Uani 1 1 d . . .
H24 H 0.3523 0.7828 0.9484 0.070 Uiso 1 1 calc R . .
C25 C 0.1759(3) 0.77303(18) 0.9248(3) 0.0647(11) Uani 1 1 d . . .
H25 H 0.1732 0.7239 0.9241 0.078 Uiso 1 1 calc R . .
C26 C 0.0744(3) 0.81202(18) 0.9119(3) 0.0609(10) Uani 1 1 d . . .
H26 H 0.0023 0.7891 0.9030 0.073 Uiso 1 1 calc R . .
C27 C 0.0781(3) 0.88463(17) 0.9121(2) 0.0504(9) Uani 1 1 d . . .
H27 H 0.0080 0.9097 0.9036 0.060 Uiso 1 1 calc R . .
C31 C -0.1597(2) 1.05576(15) 0.7364(2) 0.0354(7) Uani 1 1 d . . .
C32 C -0.1643(2) 1.07678(15) 0.8235(2) 0.0441(8) Uani 1 1 d . . .
H32 H -0.1097 1.0580 0.8809 0.053 Uiso 1 1 calc R . .
C33 C -0.2497(3) 1.12569(16) 0.8256(3) 0.0482(9) Uani 1 1 d . . .
H33 H -0.2518 1.1396 0.8843 0.058 Uiso 1 1 calc R . .
C34 C -0.3299(3) 1.15309(15) 0.7425(3) 0.0432(8) Uani 1 1 d . . .
C35 C -0.3290(3) 1.13297(16) 0.6552(3) 0.0476(9) Uani 1 1 d . . .
H35 H -0.3853 1.1514 0.5983 0.057 Uiso 1 1 calc R . .
C36 C -0.2429(2) 1.08482(16) 0.6528(2) 0.0449(8) Uani 1 1 d . . .
H36 H -0.2412 1.0718 0.5937 0.054 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 0.03084(14) 0.03858(16) 0.04085(19) -0.00500(14) 0.01469(13) 0.00102(12)
Br1 0.0617(2) 0.0502(2) 0.1315(5) 0.0035(2) 0.0511(3) 0.01550(18)
N1 0.0300(12) 0.0419(14) 0.0456(18) -0.0019(12) 0.0160(12) 0.0015(10)
N2 0.0332(13) 0.0497(15) 0.0439(19) -0.0141(13) 0.0220(13) -0.0014(11)
N3 0.0408(15) 0.071(2) 0.061(2) -0.0315(17) 0.0294(15) -0.0153(14)
N4 0.0304(13) 0.0508(15) 0.0374(17) -0.0141(14) 0.0127(12) 0.0012(11)
C1 0.0339(16) 0.050(2) 0.063(3) 0.0009(18) 0.0255(17) 0.0006(14)
C2 0.0327(17) 0.077(2) 0.074(3) -0.005(2) 0.0179(18) -0.0036(17)
C3 0.061(2) 0.072(2) 0.079(3) 0.001(2) 0.047(2) -0.0094(19)
C4 0.0453(18) 0.058(2) 0.091(3) 0.001(2) 0.038(2) 0.0094(16)
C5 0.0319(16) 0.0514(19) 0.038(2) -0.0063(16) 0.0134(15) -0.0015(14)
C6 0.0395(17) 0.058(2) 0.049(2) -0.0203(18) 0.0193(17) -0.0055(15)
C7 0.093(3) 0.046(2) 0.089(3) -0.009(2) 0.060(3) -0.002(2)
C8 0.078(2) 0.071(2) 0.051(3) -0.008(2) 0.038(2) 0.0074(19)
C9 0.0355(17) 0.053(2) 0.066(3) -0.0113(19) 0.0262(18) -0.0080(15)
C10 0.047(2) 0.136(4) 0.079(4) -0.009(3) 0.021(2) -0.025(2)
C11 0.057(2) 0.095(3) 0.098(4) 0.017(3) 0.027(2) -0.003(2)
C12 0.056(2) 0.049(2) 0.063(3) 0.006(2) 0.021(2) 0.0097(16)
C13 0.0475(19) 0.0340(18) 0.062(3) -0.0012(17) 0.0242(19) 0.0001(14)
C14 0.058(2) 0.056(2) 0.089(4) -0.016(2) 0.035(2) -0.0107(18)
C15 0.108(4) 0.088(3) 0.091(4) -0.021(3) 0.061(3) -0.015(3)
C16 0.135(4) 0.083(3) 0.066(4) -0.018(3) 0.028(4) -0.005(3)
C17 0.063(3) 0.067(3) 0.111(5) -0.017(3) 0.004(3) -0.004(2)
C18 0.051(2) 0.054(2) 0.093(4) -0.011(2) 0.028(2) 0.0018(17)
C21 0.0406(16) 0.0466(19) 0.044(2) -0.0051(16) 0.0183(16) -0.0002(13)
C22 0.0424(17) 0.0497(19) 0.032(2) 0.0017(15) 0.0163(15) -0.0001(14)
C23 0.0446(18) 0.048(2) 0.049(2) 0.0035(17) 0.0225(17) 0.0007(15)
C24 0.062(2) 0.049(2) 0.073(3) 0.0059(19) 0.037(2) 0.0109(17)
C25 0.085(3) 0.043(2) 0.081(3) 0.001(2) 0.049(2) -0.0059(19)
C26 0.060(2) 0.061(2) 0.072(3) 0.002(2) 0.036(2) -0.0137(19)
C27 0.0436(18) 0.059(2) 0.052(3) 0.0026(18) 0.0219(17) 0.0017(16)
C31 0.0256(15) 0.0468(18) 0.036(2) -0.0049(16) 0.0139(15) -0.0001(13)
C32 0.0381(17) 0.053(2) 0.042(2) -0.0026(17) 0.0157(16) 0.0079(14)
C33 0.0512(19) 0.049(2) 0.054(3) -0.0061(18) 0.0306(19) 0.0003(16)
C34 0.0360(16) 0.0381(18) 0.062(3) 0.0028(18) 0.0253(18) 0.0004(14)
C35 0.0355(17) 0.0473(19) 0.058(3) 0.0133(18) 0.0161(18) 0.0011(14)
C36 0.0392(17) 0.057(2) 0.043(2) -0.0014(17) 0.0217(17) -0.0045(15)
_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 1.763(2) . ?
Nb1 N2 2.102(2) . ?
Nb1 C12 2.211(3) . ?
Nb1 C21 2.220(3) . ?
Nb1 N4 2.367(2) . ?
Nb1 C13 2.604(3) . ?
Nb1 C5 2.685(3) . ?
Br1 C34 1.902(3) . ?
N1 C1 1.473(3) . ?
N2 C5 1.350(3) . ?
N2 C6 1.475(4) . ?
N3 C5 1.356(4) . ?
N3 C9 1.480(4) . ?
N4 C5 1.331(4) . ?
N4 C31 1.401(3) . ?
C1 C2 1.526(4) . ?
C1 C4 1.528(4) . ?
C1 C3 1.528(5) . ?
C6 C7 1.512(4) . ?
C6 C8 1.516(4) . ?
C9 C11 1.497(5) . ?
C9 C10 1.507(4) . ?
C12 C13 1.463(5) . ?
C13 C14 1.387(4) . ?
C13 C18 1.398(4) . ?
C14 C15 1.358(6) . ?
C15 C16 1.372(6) . ?
C16 C17 1.363(6) . ?
C17 C18 1.374(6) . ?
C21 C22 1.473(4) . ?
C22 C23 1.402(4) . ?
C22 C27 1.405(4) . ?
C23 C24 1.368(4) . ?
C24 C25 1.386(4) . ?
C25 C26 1.372(4) . ?
C26 C27 1.375(4) . ?
C31 C36 1.384(4) . ?
C31 C32 1.390(4) . ?
C32 C33 1.390(4) . ?
C33 C34 1.354(4) . ?
C34 C35 1.371(4) . ?
C35 C36 1.387(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 N2 103.45(10) . . ?
N1 Nb1 C12 97.79(11) . . ?
N2 Nb1 C12 110.45(12) . . ?
N1 Nb1 C21 97.35(11) . . ?
N2 Nb1 C21 118.57(10) . . ?
C12 Nb1 C21 123.05(12) . . ?
N1 Nb1 N4 162.35(10) . . ?
N2 Nb1 N4 59.42(8) . . ?
C12 Nb1 N4 92.86(10) . . ?
C21 Nb1 N4 88.48(10) . . ?
N1 Nb1 C13 98.53(10) . . ?
N2 Nb1 C13 141.20(10) . . ?
C12 Nb1 C13 34.15(11) . . ?
C21 Nb1 C13 89.33(11) . . ?
N4 Nb1 C13 98.18(9) . . ?
N1 Nb1 C5 133.04(10) . . ?
N2 Nb1 C5 29.71(8) . . ?
C12 Nb1 C5 103.21(11) . . ?
C21 Nb1 C5 105.14(10) . . ?
N4 Nb1 C5 29.72(8) . . ?
C13 Nb1 C5 121.99(9) . . ?
C1 N1 Nb1 178.0(2) . . ?
C5 N2 C6 123.4(2) . . ?
C5 N2 Nb1 99.80(18) . . ?
C6 N2 Nb1 136.00(17) . . ?
C5 N3 C9 125.7(3) . . ?
C5 N4 C31 124.0(2) . . ?
C5 N4 Nb1 88.46(16) . . ?
C31 N4 Nb1 138.74(18) . . ?
N1 C1 C2 108.3(3) . . ?
N1 C1 C4 110.2(2) . . ?
C2 C1 C4 109.8(3) . . ?
N1 C1 C3 108.0(3) . . ?
C2 C1 C3 110.2(3) . . ?
C4 C1 C3 110.2(3) . . ?
N4 C5 N2 112.3(2) . . ?
N4 C5 N3 125.0(3) . . ?
N2 C5 N3 122.7(3) . . ?
N4 C5 Nb1 61.82(14) . . ?
N2 C5 Nb1 50.49(14) . . ?
N3 C5 Nb1 173.1(2) . . ?
N2 C6 C7 110.2(3) . . ?
N2 C6 C8 109.6(3) . . ?
C7 C6 C8 112.4(3) . . ?
N3 C9 C11 111.1(3) . . ?
N3 C9 C10 108.0(3) . . ?
C11 C9 C10 110.8(3) . . ?
C13 C12 Nb1 87.8(2) . . ?
C14 C13 C18 115.7(4) . . ?
C14 C13 C12 121.4(3) . . ?
C18 C13 C12 122.5(3) . . ?
C14 C13 Nb1 104.4(2) . . ?
C18 C13 Nb1 102.4(2) . . ?
C12 C13 Nb1 58.06(16) . . ?
C15 C14 C13 122.8(4) . . ?
C14 C15 C16 120.1(4) . . ?
C17 C16 C15 119.2(5) . . ?
C16 C17 C18 120.6(4) . . ?
C17 C18 C13 121.5(4) . . ?
C22 C21 Nb1 103.4(2) . . ?
C23 C22 C27 115.4(3) . . ?
C23 C22 C21 122.2(3) . . ?
C27 C22 C21 122.3(3) . . ?
C24 C23 C22 122.3(3) . . ?
C23 C24 C25 120.8(3) . . ?
C26 C25 C24 118.5(3) . . ?
C25 C26 C27 120.8(3) . . ?
C26 C27 C22 122.2(3) . . ?
C36 C31 C32 117.8(3) . . ?
C36 C31 N4 123.1(3) . . ?
C32 C31 N4 118.9(3) . . ?
C31 C32 C33 120.5(3) . . ?
C34 C33 C32 120.2(3) . . ?
C33 C34 C35 120.9(3) . . ?
C33 C34 Br1 120.0(3) . . ?
C35 C34 Br1 119.1(3) . . ?
C34 C35 C36 119.1(3) . . ?
C31 C36 C35 121.5(3) . . ?
_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.529
_refine_diff_density_rms         0.063


data_3dH2
_database_code_depnum_ccdc_archive 'CCDC 924357'
#TrackingRef 'xray.cif'
_audit_creation_method           shelxl-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H36 N6'
_chemical_formula_weight         360.55
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
c c 0.0033 0.0016 'international tables vol c tables 4.2.6.8 and 6.1.1.4'
h h 0.0000 0.0000 'international tables vol c tables 4.2.6.8 and 6.1.1.4'
n n 0.0061 0.0033 'international tables vol c tables 4.2.6.8 and 6.1.1.4'
o o 0.0106 0.0060 'international tables vol c tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_h-m   P2(1)/c
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
_cell_length_a                   9.6476(7)
_cell_length_b                   16.4666(12)
_cell_length_c                   8.4418(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.015(5)
_cell_angle_gamma                90.00
_cell_volume                     1327.99(17)
_cell_formula_units_z            2
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    861
_cell_measurement_theta_min      4.928
_cell_measurement_theta_max      34.659
_exptl_crystal_description       Prismatic
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    0.902
_exptl_crystal_density_method    'not measured'
_exptl_crystal_f_000             396
_exptl_absorpt_coefficient_mu    0.056
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_t_min  0.9046
_exptl_absorpt_correction_t_max  0.9896
_exptl_absorpt_process_details   
'SADABS Version 2008/1 (Sheldrick, Bruker AXS Inc.)'
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      300(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 scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11614
_diffrn_reflns_av_r_equivalents  0.0651
_diffrn_reflns_av_sigmai/neti    0.0630
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.47
_diffrn_reflns_theta_max         25.09
_reflns_number_total             2354
_reflns_number_gt                1244
_reflns_threshold_expression     >2sigma(i)
_computing_data_collection       'Apex2, Bruker Instrument Service v2010, 1-2'
_computing_cell_refinement       
'SAINT V7.68A (Bruker: Madison, 2009 ) in Apex2 suite'
_computing_data_reduction        
'SAINT and XPREP Version 2008/2 (Sheldrick, Bruker AXS Inc.)'
_computing_structure_solution    
'XS Version 2008/1 (George M. Sheldrick, Acta Cryst. (2008). A64, 112-122)'
_computing_structure_refinement  
'XL Version 2008/4 (George M. Sheldrick, Acta Cryst. (2008). A64, 112-122)'
_computing_molecular_graphics    'Bruker SHELXTL and ORTEP III'
_computing_publication_material  'Bruker SHELXTL and WinGX'
_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. One-half of a very disordered
THF solvent molecule was found in the asymmetric unit of 3dH2 which was
removed using the program SQUEEZE implemented in Platon.
;
_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^)+(0.1185P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.054(9)
_refine_ls_number_reflns         2354
_refine_ls_number_parameters     126
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1171
_refine_ls_R_factor_gt           0.0678
_refine_ls_wR_factor_ref         0.2029
_refine_ls_wR_factor_gt          0.1809
_refine_ls_goodness_of_fit_ref   0.921
_refine_ls_restrained_S_all      0.921
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4525(2) 0.29755(14) 0.1783(3) 0.0515(7) Uani 1 1 d . . .
C9 C 0.4761(3) 0.41658(14) 0.0276(2) 0.0514(7) Uani 1 1 d . . .
C3 C 0.1327(4) 0.2337(3) 0.1438(5) 0.1155(13) Uani 1 1 d . . .
H3C H 0.1392 0.2916 0.1543 0.173 Uiso 1 1 calc R . .
H3B H 0.1244 0.2100 0.2459 0.173 Uiso 1 1 calc R . .
H3A H 0.0519 0.2198 0.0689 0.173 Uiso 1 1 calc R . .
C2 C 0.2606(3) 0.20199(16) 0.0852(3) 0.0677(8) Uani 1 1 d . . .
H2A H 0.2651 0.2253 -0.0208 0.081 Uiso 1 1 calc R . .
C4 C 0.2571(4) 0.1106(2) 0.0690(5) 0.1164(13) Uani 1 1 d . . .
H4C H 0.3408 0.0923 0.0306 0.175 Uiso 1 1 calc R . .
H4A H 0.1769 0.0950 -0.0052 0.175 Uiso 1 1 calc R . .
H4B H 0.2512 0.0866 0.1715 0.175 Uiso 1 1 calc R . .
C6 C 0.6619(3) 0.36301(17) 0.3355(3) 0.0700(8) Uani 1 1 d . . .
H6A H 0.6555 0.4096 0.2627 0.084 Uiso 1 1 calc R . .
C7 C 0.7730(4) 0.3060(3) 0.2918(5) 0.1284(15) Uani 1 1 d . . .
H7B H 0.7485 0.2884 0.1831 0.193 Uiso 1 1 calc R . .
H7A H 0.7797 0.2597 0.3616 0.193 Uiso 1 1 calc R . .
H7C H 0.8615 0.3336 0.3029 0.193 Uiso 1 1 calc R . .
C8 C 0.6986(4) 0.3933(2) 0.5034(4) 0.1008(12) Uani 1 1 d . . .
H8A H 0.6275 0.4302 0.5279 0.151 Uiso 1 1 calc R . .
H8B H 0.7871 0.4209 0.5138 0.151 Uiso 1 1 calc R . .
H8C H 0.7047 0.3483 0.5762 0.151 Uiso 1 1 calc R . .
C10 C 0.5567(3) 0.44227(14) -0.0873(3) 0.0589(7) Uani 1 1 d . . .
H10 H 0.5956 0.4038 -0.1485 0.071 Uiso 1 1 calc R . .
C11 C 0.4200(3) 0.47644(15) 0.1125(3) 0.0591(7) Uani 1 1 d . . .
H11 H 0.3645 0.4617 0.1894 0.071 Uiso 1 1 calc R . .
H1 H 0.396(3) 0.2073(16) 0.276(3) 0.066(9) Uiso 1 1 d . . .
N3 N 0.4450(2) 0.33363(11) 0.0410(2) 0.0577(6) Uani 1 1 d . . .
N2 N 0.5262(2) 0.32357(14) 0.3207(2) 0.0644(7) Uani 1 1 d D . .
N1 N 0.3866(3) 0.22533(13) 0.1892(3) 0.0639(7) Uani 1 1 d . . .
H2 H 0.518(3) 0.2917(13) 0.401(2) 0.077 Uiso 1 1 d D . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0694(16) 0.0430(14) 0.0429(14) 0.0009(11) 0.0102(12) 0.0011(12)
C9 0.0755(16) 0.0432(15) 0.0354(12) 0.0002(10) 0.0072(11) -0.0044(12)
C3 0.089(2) 0.127(3) 0.124(3) -0.020(2) -0.008(2) 0.002(2)
C2 0.088(2) 0.0579(17) 0.0553(16) 0.0004(12) 0.0034(15) -0.0194(14)
C4 0.136(3) 0.068(2) 0.145(3) -0.022(2) 0.018(3) -0.027(2)
C6 0.080(2) 0.0690(18) 0.0583(17) 0.0078(13) 0.0010(14) -0.0120(15)
C7 0.086(2) 0.154(4) 0.145(4) -0.053(3) 0.019(2) -0.005(2)
C8 0.129(3) 0.087(2) 0.078(2) -0.0130(16) -0.013(2) -0.025(2)
C10 0.0877(18) 0.0449(16) 0.0473(14) -0.0029(11) 0.0206(14) -0.0004(12)
C11 0.0854(18) 0.0510(16) 0.0446(14) 0.0020(11) 0.0218(13) -0.0042(13)
N3 0.0900(16) 0.0414(12) 0.0422(12) 0.0006(9) 0.0107(10) -0.0060(10)
N2 0.0801(16) 0.0684(15) 0.0437(13) 0.0071(10) 0.0060(11) -0.0137(12)
N1 0.0869(17) 0.0508(15) 0.0533(15) 0.0112(11) 0.0076(13) -0.0091(12)
_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 N3 1.296(3) . ?
C1 N1 1.358(3) . ?
C1 N2 1.376(3) . ?
C9 C11 1.373(3) . ?
C9 C10 1.391(3) . ?
C9 N3 1.406(3) . ?
C3 C2 1.487(4) . ?
C3 H3C 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3A 0.9600 . ?
C2 N1 1.448(3) . ?
C2 C4 1.510(4) . ?
C2 H2A 0.9800 . ?
C4 H4C 0.9600 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C6 N2 1.452(3) . ?
C6 C8 1.498(4) . ?
C6 C7 1.509(4) . ?
C6 H6A 0.9800 . ?
C7 H7B 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C10 C11 1.379(3) 3_665 ?
C10 H10 0.9300 . ?
C11 C10 1.379(3) 3_665 ?
C11 H11 0.9300 . ?
N2 H2 0.867(10) . ?
N1 H1 0.79(3) . ?
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
N3 C1 N1 119.6(2) . . ?
N3 C1 N2 126.6(2) . . ?
N1 C1 N2 113.8(2) . . ?
C11 C9 C10 116.4(2) . . ?
C11 C9 N3 123.4(2) . . ?
C10 C9 N3 119.8(2) . . ?
C2 C3 H3C 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3C C3 H3B 109.5 . . ?
C2 C3 H3A 109.5 . . ?
H3C C3 H3A 109.5 . . ?
H3B C3 H3A 109.5 . . ?
N1 C2 C3 111.8(2) . . ?
N1 C2 C4 109.0(3) . . ?
C3 C2 C4 111.7(3) . . ?
N1 C2 H2A 108.1 . . ?
C3 C2 H2A 108.1 . . ?
C4 C2 H2A 108.1 . . ?
C2 C4 H4C 109.5 . . ?
C2 C4 H4A 109.5 . . ?
H4C C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
H4C C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N2 C6 C8 108.8(2) . . ?
N2 C6 C7 111.3(3) . . ?
C8 C6 C7 110.9(3) . . ?
N2 C6 H6A 108.6 . . ?
C8 C6 H6A 108.6 . . ?
C7 C6 H6A 108.6 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7A 109.5 . . ?
H7B C7 H7A 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C11 C10 C9 121.5(2) 3_665 . ?
C11 C10 H10 119.3 3_665 . ?
C9 C10 H10 119.3 . . ?
C9 C11 C10 122.1(2) . 3_665 ?
C9 C11 H11 118.9 . . ?
C10 C11 H11 118.9 3_665 . ?
C1 N3 C9 122.08(19) . . ?
C1 N2 C6 124.4(2) . . ?
C1 N2 H2 113.7(18) . . ?
C6 N2 H2 112.2(18) . . ?
C1 N1 C2 123.6(2) . . ?
C1 N1 H1 113(2) . . ?
C2 N1 H1 117(2) . . ?
_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.09
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.057
# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.500 -0.001 157 15 ' '
2 0.000 0.000 0.495 157 15 ' '
_platon_squeeze_details          
;
;
#=======================================================================_eof
# End of Crystallographic Information File