##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
N,N-Bis(2-pyridylmethyl)-tert-butylamine
;
_chemical_name_common     'N,N bis(2-pyridylmethyltert-butylamine'
_chemical_formula_moiety     'C16 H21 N3'
_chemical_formula_sum     'C16 H21 N3'
_chemical_formula_iupac     'C16 H21 N3'
_chemical_formula_weight     255.36
_chemical_melting_point     ?
_symmetry_cell_setting     'monoclinic'
_symmetry_space_group_name_H-M     'C c'
_symmetry_space_group_name_hall     'C -2yc'
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'
_cell_length_a     6.1808(3)
_cell_length_b     17.9502(8)
_cell_length_c     13.7079(6)
_cell_angle_alpha     90.00
_cell_angle_beta     100.239(4)
_cell_angle_gamma     90.00
_cell_volume     1496.62(12)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     4672
_cell_measurement_theta_min     3.9012
_cell_measurement_theta_max     31.9570
_cell_measurement_temperature     293(2)
_exptl_crystal_description     'plate'
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.50
_exptl_crystal_size_mid     0.50
_exptl_crystal_size_min     0.30
_exptl_crystal_density_diffrn     1.133
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     552
_exptl_absorpt_coefficient_mu     0.068
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2008)
;
_exptl_absorpt_correction_T_min     0.9666
_exptl_absorpt_correction_T_max     0.9798
_exptl_special_details
;
;
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'Enhance (Mo)X-Ray Source'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Oxford Diffraction Xcalibur2 CCD'
_diffrn_measurement_method     'ω-2θ'
_diffrn_detector_area_resol_mean     8.4190
_diffrn_reflns_number     7475
_diffrn_reflns_av_R_equivalents     0.0122
_diffrn_reflns_av_sigmaI/netI     0.0145
_diffrn_reflns_theta_min     4.07
_diffrn_reflns_theta_max     31.89
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.929
_diffrn_measured_fraction_theta_full     0.995
_diffrn_reflns_limit_h_min     -8
_diffrn_reflns_limit_h_max     7
_diffrn_reflns_limit_k_min     -26
_diffrn_reflns_limit_k_max     26
_diffrn_reflns_limit_l_min     -18
_diffrn_reflns_limit_l_max     20
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_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 >
σ(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.
;
_reflns_number_total     2392
_reflns_number_gt     2024
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0511
_refine_ls_R_factor_gt     0.0427
_refine_ls_wR_factor_gt     0.1146
_refine_ls_wR_factor_ref     0.1194
_refine_ls_goodness_of_fit_ref     1.021
_refine_ls_restrained_S_all     1.021
_refine_ls_number_reflns     2392
_refine_ls_number_parameters     175
_refine_ls_number_restraints     2
_refine_ls_number_constraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
          'calc w=1/[σ²(Fo²)+(0.0873P)²+0.017P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.206
_refine_diff_density_min     -0.215
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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 0.0000
                         '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 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'CrysAlis CCD (Oxford Diffraction, 2008)'
_computing_cell_refinement     'CrysAlis RED (Oxford Diffraction, 2008)'
_computing_data_reduction     'CrysAlis RED (Oxford Diffraction, 2008)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material     'WinGX (Farrugia, 1999)'
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C14 0.2251(5) 0.16330(11) 0.59751(18) 0.0645(6) Uani d . 1 . .
    H H20 0.1452 0.1875 0.6425 0.097 Uiso calc R 1 . .
    H H21 0.2314 0.1955 0.5421 0.097 Uiso calc R 1 . .
    H H19 0.3716 0.1525 0.6311 0.097 Uiso calc R 1 . .
    C C15 0.2342(5) 0.05704(14) 0.48509(17) 0.0679(6) Uani d . 1 . .
    H H18 0.3767 0.0409 0.5180 0.102 Uiso calc R 1 . .
    H H16 0.2508 0.0937 0.4359 0.102 Uiso calc R 1 . .
    H H17 0.1537 0.0152 0.4537 0.102 Uiso calc R 1 . .
    C C16 -0.1269(5) 0.10773(16) 0.5103(2) 0.0739(7) Uani d . 1 . .
    H H15 -0.1940 0.0630 0.4806 0.111 Uiso calc R 1 . .
    H H14 -0.1260 0.1449 0.4600 0.111 Uiso calc R 1 . .
    H H13 -0.2090 0.1258 0.5586 0.111 Uiso calc R 1 . .
    N N3 0.1632(2) 0.14031(8) 0.88126(11) 0.0448(3) Uani d . 1 . .
    C C9 0.2329(2) 0.09809(8) 0.81277(11) 0.0365(3) Uani d . 1 . .
    N N1 0.1221(2) 0.03781(7) 0.64559(9) 0.0382(3) Uani d . 1 . .
    C C3 0.1172(3) -0.09657(8) 0.68278(12) 0.0384(3) Uani d . 1 . .
    C C10 0.4530(3) 0.08012(10) 0.81845(13) 0.0434(3) Uani d . 1 . .
    H H8 0.4982 0.0513 0.7694 0.052 Uiso calc R 1 . .
    C C1 0.1094(3) 0.09104(10) 0.56073(13) 0.0455(4) Uani d . 1 . .
    C C2 0.0134(3) -0.03384(10) 0.61861(13) 0.0452(4) Uani d . 1 . .
    H H11 0.0200 -0.0449 0.5499 0.054 Uiso calc R 1 . .
    H H12 -0.1403 -0.0300 0.6245 0.054 Uiso calc R 1 . .
    N N2 -0.0196(2) -0.14516(8) 0.71406(13) 0.0476(3) Uani d . 1 . .
    C C8 0.0527(3) 0.06774(11) 0.73393(12) 0.0442(4) Uani d . 1 . .
    H H9 -0.0232 0.0287 0.7633 0.053 Uiso calc R 1 . .
    H H10 -0.0527 0.1073 0.7137 0.053 Uiso calc R 1 . .
    C C12 0.5344(3) 0.14791(10) 0.96934(14) 0.0529(4) Uani d . 1 . .
    H H6 0.6329 0.1652 1.0240 0.063 Uiso calc R 1 . .
    C C11 0.6047(3) 0.10564(11) 0.89812(15) 0.0501(4) Uani d . 1 . .
    H H7 0.7530 0.0941 0.9031 0.060 Uiso calc R 1 . .
    C C4 0.3437(3) -0.10609(10) 0.70322(14) 0.0466(4) Uani d . 1 . .
    H H4 0.4352 -0.0713 0.6809 0.056 Uiso calc R 1 . .
    C C13 0.3140(4) 0.16421(10) 0.95790(14) 0.0519(4) Uani d . 1 . .
    H H5 0.2664 0.1935 1.0060 0.062 Uiso calc R 1 . .
    C C5 0.4322(3) -0.16716(12) 0.75666(16) 0.0553(5) Uani d . 1 . .
    H H3 0.5836 -0.1743 0.7708 0.066 Uiso calc R 1 . .
    C C6 0.2920(4) -0.21757(11) 0.78883(17) 0.0567(5) Uani d . 1 . .
    H H2 0.3460 -0.2594 0.8252 0.068 Uiso calc R 1 . .
    C C7 0.0701(3) -0.20409(10) 0.76555(17) 0.0554(5) Uani d . 1 . .
    H H1 -0.0242 -0.2383 0.7871 0.066 Uiso calc R 1 . .
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    C14 0.0927(17) 0.0403(9) 0.0584(12) -0.0074(10) 0.0077(11) 0.0060(8)
    C15 0.0990(18) 0.0620(12) 0.0486(11) -0.0019(12) 0.0296(11) 0.0014(9)
    C16 0.0720(14) 0.0773(16) 0.0638(13) 0.0155(12) -0.0114(11) 0.0176(11)
    N3 0.0476(8) 0.0460(7) 0.0408(7) 0.0030(6) 0.0075(6) -0.0021(5)
    C9 0.0370(7) 0.0395(7) 0.0324(6) -0.0014(5) 0.0047(5) 0.0033(5)
    N1 0.0426(7) 0.0397(6) 0.0307(6) -0.0034(5) 0.0021(5) 0.0008(4)
    C3 0.0404(8) 0.0389(7) 0.0347(7) -0.0029(6) 0.0033(5) -0.0005(5)
    C10 0.0369(7) 0.0529(9) 0.0396(7) 0.0002(6) 0.0044(6) -0.0019(6)
    C1 0.0559(10) 0.0416(8) 0.0371(7) 0.0006(6) 0.0034(7) 0.0054(6)
    C2 0.0446(8) 0.0451(8) 0.0409(8) -0.0067(6) -0.0060(6) 0.0039(6)
    N2 0.0412(7) 0.0437(7) 0.0568(9) -0.0058(6) 0.0056(6) 0.0045(6)
    C8 0.0342(7) 0.0603(10) 0.0369(7) -0.0018(6) 0.0031(6) -0.0030(6)
    C12 0.0612(11) 0.0493(9) 0.0427(9) -0.0136(8) -0.0054(8) 0.0022(7)
    C11 0.0403(8) 0.0573(10) 0.0493(9) -0.0036(7) -0.0013(7) 0.0072(7)
    C4 0.0371(8) 0.0526(9) 0.0514(9) -0.0026(6) 0.0114(7) 0.0003(7)
    C13 0.0678(11) 0.0456(8) 0.0413(9) -0.0018(8) 0.0071(8) -0.0066(7)
    C5 0.0433(9) 0.0576(10) 0.0637(12) 0.0114(8) 0.0061(8) -0.0027(9)
    C6 0.0618(11) 0.0419(8) 0.0640(11) 0.0110(7) 0.0043(9) 0.0033(8)
    C7 0.0539(10) 0.0426(9) 0.0702(12) -0.0057(7) 0.0127(9) 0.0088(8)
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    C14 C1 . 1.523(3) ?
    C14 H20 . 0.9600 ?
    C14 H21 . 0.9600 ?
    C14 H19 . 0.9600 ?
    C15 C1 . 1.525(3) ?
    C15 H18 . 0.9600 ?
    C15 H16 . 0.9600 ?
    C15 H17 . 0.9600 ?
    C16 C1 . 1.531(3) ?
    C16 H15 . 0.9600 ?
    C16 H14 . 0.9600 ?
    C16 H13 . 0.9600 ?
    N3 C9 . 1.336(2) ?
    N3 C13 . 1.345(2) ?
    C9 C10 . 1.387(2) ?
    C9 C8 . 1.509(2) ?
    N1 C8 . 1.457(2) ?
    N1 C2 . 1.468(2) ?
    N1 C1 . 1.497(2) ?
    C3 N2 . 1.338(2) ?
    C3 C4 . 1.388(2) ?
    C3 C2 . 1.501(2) ?
    C10 C11 . 1.385(2) ?
    C10 H8 . 0.9300 ?
    C2 H11 . 0.9700 ?
    C2 H12 . 0.9700 ?
    N2 C7 . 1.336(2) ?
    C8 H9 . 0.9700 ?
    C8 H10 . 0.9700 ?
    C12 C11 . 1.367(3) ?
    C12 C13 . 1.375(3) ?
    C12 H6 . 0.9300 ?
    C11 H7 . 0.9300 ?
    C4 C5 . 1.377(3) ?
    C4 H4 . 0.9300 ?
    C13 H5 . 0.9300 ?
    C5 C6 . 1.378(3) ?
    C5 H3 . 0.9300 ?
    C6 C7 . 1.374(3) ?
    C6 H2 . 0.9300 ?
    C7 H1 . 0.9300 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C1 C14 H20 . . 109.5 ?
    C1 C14 H21 . . 109.5 ?
    H20 C14 H21 . . 109.5 ?
    C1 C14 H19 . . 109.5 ?
    H20 C14 H19 . . 109.5 ?
    H21 C14 H19 . . 109.5 ?
    C1 C15 H18 . . 109.5 ?
    C1 C15 H16 . . 109.5 ?
    H18 C15 H16 . . 109.5 ?
    C1 C15 H17 . . 109.5 ?
    H18 C15 H17 . . 109.5 ?
    H16 C15 H17 . . 109.5 ?
    C1 C16 H15 . . 109.5 ?
    C1 C16 H14 . . 109.5 ?
    H15 C16 H14 . . 109.5 ?
    C1 C16 H13 . . 109.5 ?
    H15 C16 H13 . . 109.5 ?
    H14 C16 H13 . . 109.5 ?
    C9 N3 C13 . . 117.70(16) ?
    N3 C9 C10 . . 121.88(15) ?
    N3 C9 C8 . . 114.75(14) ?
    C10 C9 C8 . . 123.24(14) ?
    C8 N1 C2 . . 110.06(14) ?
    C8 N1 C1 . . 115.35(14) ?
    C2 N1 C1 . . 113.90(12) ?
    N2 C3 C4 . . 121.83(15) ?
    N2 C3 C2 . . 116.63(15) ?
    C4 C3 C2 . . 121.42(15) ?
    C11 C10 C9 . . 119.16(17) ?
    C11 C10 H8 . . 120.4 ?
    C9 C10 H8 . . 120.4 ?
    N1 C1 C14 . . 109.25(14) ?
    N1 C1 C15 . . 108.06(15) ?
    C14 C1 C15 . . 107.53(19) ?
    N1 C1 C16 . . 112.96(17) ?
    C14 C1 C16 . . 109.70(18) ?
    C15 C1 C16 . . 109.18(19) ?
    N1 C2 C3 . . 112.38(12) ?
    N1 C2 H11 . . 109.1 ?
    C3 C2 H11 . . 109.1 ?
    N1 C2 H12 . . 109.1 ?
    C3 C2 H12 . . 109.1 ?
    H11 C2 H12 . . 107.9 ?
    C7 N2 C3 . . 117.31(16) ?
    N1 C8 C9 . . 116.05(14) ?
    N1 C8 H9 . . 108.3 ?
    C9 C8 H9 . . 108.3 ?
    N1 C8 H10 . . 108.3 ?
    C9 C8 H10 . . 108.3 ?
    H9 C8 H10 . . 107.4 ?
    C11 C12 C13 . . 118.10(17) ?
    C11 C12 H6 . . 121.0 ?
    C13 C12 H6 . . 121.0 ?
    C12 C11 C10 . . 119.36(17) ?
    C12 C11 H7 . . 120.3 ?
    C10 C11 H7 . . 120.3 ?
    C5 C4 C3 . . 119.78(16) ?
    C5 C4 H4 . . 120.1 ?
    C3 C4 H4 . . 120.1 ?
    N3 C13 C12 . . 123.79(17) ?
    N3 C13 H5 . . 118.1 ?
    C12 C13 H5 . . 118.1 ?
    C4 C5 C6 . . 118.68(17) ?
    C4 C5 H3 . . 120.7 ?
    C6 C5 H3 . . 120.7 ?
    C7 C6 C5 . . 117.95(18) ?
    C7 C6 H2 . . 121.0 ?
    C5 C6 H2 . . 121.0 ?
    N2 C7 C6 . . 124.45(18) ?
    N2 C7 H1 . . 117.8 ?
    C6 C7 H1 . . 117.8 ?
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C13 N3 C9 C10 . . . . -1.1(2) ?
    C13 N3 C9 C8 . . . . 174.86(16) ?
    N3 C9 C10 C11 . . . . 1.0(2) ?
    C8 C9 C10 C11 . . . . -174.62(17) ?
    C8 N1 C1 C14 . . . . 50.8(2) ?
    C2 N1 C1 C14 . . . . 179.45(17) ?
    C8 N1 C1 C15 . . . . 167.47(17) ?
    C2 N1 C1 C15 . . . . -63.8(2) ?
    C8 N1 C1 C16 . . . . -71.6(2) ?
    C2 N1 C1 C16 . . . . 57.1(2) ?
    C8 N1 C2 C3 . . . . -77.86(18) ?
    C1 N1 C2 C3 . . . . 150.82(15) ?
    N2 C3 C2 N1 . . . . 137.29(16) ?
    C4 C3 C2 N1 . . . . -46.7(2) ?
    C4 C3 N2 C7 . . . . -0.5(3) ?
    C2 C3 N2 C7 . . . . 175.54(17) ?
    C2 N1 C8 C9 . . . . 134.62(15) ?
    C1 N1 C8 C9 . . . . -94.82(18) ?
    N3 C9 C8 N1 . . . . 165.09(14) ?
    C10 C9 C8 N1 . . . . -19.0(2) ?
    C13 C12 C11 C10 . . . . -0.8(3) ?
    C9 C10 C11 C12 . . . . 0.0(3) ?
    N2 C3 C4 C5 . . . . 0.3(3) ?
    C2 C3 C4 C5 . . . . -175.51(17) ?
    C9 N3 C13 C12 . . . . 0.3(3) ?
    C11 C12 C13 N3 . . . . 0.7(3) ?
    C3 C4 C5 C6 . . . . -0.1(3) ?
    C4 C5 C6 C7 . . . . 0.1(3) ?
    C3 N2 C7 C6 . . . . 0.5(3) ?
    C5 C6 C7 N2 . . . . -0.3(3) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    C7 H1 Cg2 3_445 0.93 2.97 3.819(2) 153
    C15 H16 Cg1 2_554 0.96 2.94 3.836(2) 156
data_global
_journal_date_recd_electronic     2008-10-29
_journal_date_accepted     2009-01-12
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2009
_journal_volume     65
_journal_issue      2
_journal_page_first     o402
_journal_page_last     o402
_journal_paper_category     QO
_journal_coeditor_code     IS2355
_publ_contact_author_name     'Kirsty Stewart'
_publ_contact_author_address
;
School of Chemical and Physical Sciences, University of KwaZulu-Natal,
Scottsville, 3209, South Africa
;
_publ_contact_author_email     'stewart@ukzn.ac.za'
_publ_contact_author_fax     '0332605009'
_publ_contact_author_phone     '0332605272'
_publ_section_title
;
N,N-Bis(2-pyridylmethyl)-tert-butylamine
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Mambanda, Allen' .
;
School of Chemical and Physical Sciences, University of KwaZulu--Natal,
Scottsville 3209, South Africa
;
    'Jaganyi, Deogratius' .
;
School of Chemical and Physical Sciences, University of KwaZulu--Natal,
Scottsville 3209, South Africa
;
    'Stewart, Kirsty' .
;
School of Chemical and Physical Sciences, University of KwaZulu--Natal,
Scottsville 3209, South Africa
;
