N,N,N',N'-Tetrakis(2-pyridyl­methyl)-1,2-di­amino­ethane: a multidentate ligand

The reaction of 1,2-di­amino­ethane and 2-pyridinecarboxy­aldehyde in the presence of a reducing agent, sodium tri­acetoxy­borohydride, leads to the title compound, C₂₆H₂₈N₆. The mol­ecule has a centre of symmetry.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.054
• wR factor = 0.142
• Data-to-parameter ratio = 15.1

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Computing details

Data collection: SMART-W2K/NT (Bruker, 2003); cell refinement: SMART-W2K/NT; data reduction: SAINT-W2K/NT (Bruker, 2003); program(s) used to solve structure: SHELXTL-NT (Bruker, 2003); program(s) used to refine structure: SHELXTL-NT; molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXTL-NT.

N,N,N',N'-Tetrakis(2-pyridylmethyl)-1,2-diaminoethane

Crystal data

C26H28N6	Z = 1
Mr = 424.54	F(000) = 226
Triclinic, P1	Dx = 1.179 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.228 (1) Å	Cell parameters from 954 reflections
b = 9.482 (2) Å	θ = 2.7–22.9°
c = 10.760 (2) Å	µ = 0.07 mm^−1
α = 77.66 (3)°	T = 298 K
β = 87.74 (3)°	Prism, colourless
γ = 74.47 (3)°	0.48 × 0.45 × 0.35 mm
V = 598.0 (2) Å^3

Data collection

Bruker SMART APEX CCD area-detector diffractometer	2824 independent reflections
Radiation source: fine-focus sealed tube	1800 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.018
Detector resolution: 8.366 pixels mm^-1	θmax = 27.9°, θmin = 1.9°
φ and ω scans	h = −8→8
Absorption correction: empirical (using intensity measurements) (SADABS; Scheldrick, 1996)	k = −12→10
Tmin = 0.966, Tmax = 0.977	l = −14→13
4392 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.054	Hydrogen site location: difference Fourier map
wR(F^2) = 0.142	Only H-atom coordinates refined
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0689P)^2 + 0.0224P] where P = (Fo^2 + 2Fc^2)/3
2824 reflections	(Δ/σ)max < 0.001
187 parameters	Δρmax = 0.12 e Å^−3
0 restraints	Δρmin = −0.12 e Å^−3

Special details

Experimental. ? #Insert any special details here.

Geometry. Mean-plane data from final SHELXL refinement run:-

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

0.5024 (0.0057) x - 3.2819 (0.0072) y + 8.8452 (0.0066) z = 2.9039 (0.0028)

* 0.0023 (0.0011) C3 * -0.0006 (0.0008) C4 * -0.0013 (0.0009) C6 * 0.0032 (0.0012) C7 * -0.0037 (0.0010) N2

Rms deviation of fitted atoms = 0.0025

0.9886 (0.0045) x + 6.3156 (0.0066) y + 9.3717 (0.0065) z = 5.0488 (0.0044)

Angle to previous plane (with approximate e.s.d.) = 63.11 (0.06)

* -0.0044 (0.0011) C9 * 0.0025 (0.0012) C10 * 0.0023 (0.0013) C11 * -0.0053 (0.0013) C12 * 0.0036 (0.0013) C13 * 0.0013 (0.0011) N3

Rms deviation of fitted atoms = 0.0035

Refinement. 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.0300 (2)	0.39675 (13)	0.36619 (12)	0.0538 (4)
N2	0.0892 (2)	0.02657 (14)	0.33271 (13)	0.0577 (4)
N3	−0.1486 (2)	0.68340 (15)	0.09403 (13)	0.0643 (4)
C1	−0.0729 (3)	0.50526 (19)	0.44404 (17)	0.0588 (4)
C2	0.0152 (3)	0.24517 (17)	0.42498 (18)	0.0599 (4)
C3	0.1732 (3)	0.12822 (16)	0.36635 (14)	0.0510 (4)
C4	0.3953 (3)	0.1250 (2)	0.35211 (18)	0.0678 (5)
C5	0.5366 (3)	0.0118 (2)	0.30220 (19)	0.0778 (6)
C6	0.4514 (4)	−0.0928 (2)	0.26823 (19)	0.0753 (6)
C7	0.2295 (4)	−0.0819 (2)	0.28548 (18)	0.0690 (5)
C8	−0.0708 (3)	0.4430 (2)	0.23878 (16)	0.0605 (5)
C9	0.0080 (3)	0.56677 (16)	0.15541 (14)	0.0505 (4)
C10	0.2310 (3)	0.5580 (2)	0.13853 (18)	0.0671 (5)
C11	0.2958 (4)	0.6699 (2)	0.05638 (19)	0.0743 (5)
C12	0.1363 (4)	0.7884 (2)	−0.00757 (18)	0.0729 (5)
C13	−0.0814 (4)	0.7915 (2)	0.01424 (19)	0.0756 (5)
H1A	−0.221 (3)	0.4906 (17)	0.4768 (16)	0.071*
H1B	−0.093 (3)	0.6066 (19)	0.3876 (16)	0.071*
H2A	−0.142 (3)	0.2319 (18)	0.4227 (16)	0.072*
H2B	0.054 (3)	0.2263 (18)	0.5172 (19)	0.072*
H4	0.451 (3)	0.199 (2)	0.3766 (18)	0.081*
H5	0.685 (4)	0.015 (2)	0.2968 (19)	0.093*
H6	0.539 (3)	−0.172 (2)	0.2275 (18)	0.090*
H7	0.164 (3)	−0.153 (2)	0.2563 (17)	0.083*
H8A	−0.238 (3)	0.4707 (19)	0.2416 (17)	0.073*
H8B	−0.031 (3)	0.353 (2)	0.1993 (16)	0.073*
H10	0.332 (3)	0.472 (2)	0.1842 (17)	0.081*
H11	0.446 (4)	0.663 (2)	0.0446 (19)	0.089*
H12	0.175 (3)	0.873 (2)	−0.0652 (19)	0.088*
H13	−0.196 (3)	0.877 (2)	−0.0311 (19)	0.091*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0673 (9)	0.0435 (7)	0.0520 (8)	−0.0148 (6)	−0.0001 (6)	−0.0129 (6)
N2	0.0650 (9)	0.0502 (8)	0.0616 (8)	−0.0190 (7)	0.0087 (7)	−0.0164 (6)
N3	0.0602 (9)	0.0640 (9)	0.0610 (9)	−0.0061 (7)	−0.0020 (7)	−0.0095 (7)
C1	0.0636 (11)	0.0503 (9)	0.0626 (10)	−0.0099 (8)	−0.0019 (8)	−0.0184 (8)
C2	0.0700 (12)	0.0489 (9)	0.0626 (11)	−0.0188 (8)	0.0128 (9)	−0.0140 (8)
C3	0.0589 (10)	0.0433 (8)	0.0485 (9)	−0.0132 (7)	0.0016 (7)	−0.0049 (6)
C4	0.0576 (11)	0.0677 (12)	0.0796 (13)	−0.0201 (9)	0.0004 (9)	−0.0145 (9)
C5	0.0526 (11)	0.0844 (14)	0.0809 (14)	−0.0043 (11)	0.0043 (10)	−0.0024 (11)
C6	0.0812 (15)	0.0612 (12)	0.0690 (12)	0.0024 (10)	0.0136 (10)	−0.0116 (9)
C7	0.0876 (14)	0.0563 (10)	0.0671 (11)	−0.0200 (10)	0.0135 (10)	−0.0222 (9)
C8	0.0699 (12)	0.0578 (10)	0.0588 (10)	−0.0207 (9)	−0.0070 (9)	−0.0171 (8)
C9	0.0563 (10)	0.0510 (9)	0.0452 (8)	−0.0092 (7)	−0.0036 (7)	−0.0180 (7)
C10	0.0577 (11)	0.0645 (11)	0.0751 (12)	−0.0099 (9)	−0.0054 (9)	−0.0131 (9)
C11	0.0649 (12)	0.0892 (14)	0.0769 (13)	−0.0280 (12)	0.0112 (10)	−0.0274 (11)
C12	0.0936 (16)	0.0729 (13)	0.0568 (11)	−0.0335 (12)	0.0051 (10)	−0.0097 (9)
C13	0.0845 (15)	0.0632 (11)	0.0664 (12)	−0.0080 (10)	−0.0071 (10)	0.0003 (9)

Geometric parameters (Å, º)

N1—C8	1.459 (2)	C2—H2A	1.03 (2)
N1—C1	1.464 (2)	C2—H2B	1.00 (2)
N1—C2	1.467 (2)	C4—C5	1.384 (3)
N2—C3	1.330 (2)	C4—H4	0.95 (2)
N2—C7	1.337 (2)	C7—C6	1.366 (3)
N3—C9	1.331 (2)	C7—H7	0.99 (2)
N3—C13	1.337 (2)	C13—C12	1.361 (3)
C3—C4	1.379 (2)	C13—H13	0.98 (2)
C3—C2	1.504 (2)	C10—C11	1.368 (3)
C9—C10	1.376 (2)	C10—H10	0.94 (2)
C9—C8	1.499 (2)	C5—C6	1.361 (3)
C1—C1^i	1.507 (3)	C5—H5	0.93 (2)
C1—H1A	1.01 (2)	C11—C12	1.360 (3)
C1—H1B	1.00 (2)	C11—H11	0.92 (2)
C8—H8A	1.01 (2)	C6—H6	0.98 (2)
C8—H8B	1.00 (2)	C12—H12	0.98 (2)
C8—N1—C1	110.61 (13)	C3—C2—H2B	109.0 (10)
C8—N1—C2	110.19 (13)	H2A—C2—H2B	104.9 (14)
C1—N1—C2	112.02 (13)	C3—C4—C5	119.23 (19)
C3—N2—C7	117.41 (15)	C3—C4—H4	120.6 (12)
C9—N3—C13	117.54 (16)	C5—C4—H4	120.1 (12)
N2—C3—C4	122.11 (15)	N2—C7—C6	124.02 (19)
N2—C3—C2	116.69 (14)	N2—C7—H7	116.9 (11)
C4—C3—C2	121.18 (15)	C6—C7—H7	119.0 (11)
N3—C9—C10	121.40 (16)	N3—C13—C12	123.81 (19)
N3—C9—C8	116.65 (15)	N3—C13—H13	118.0 (12)
C10—C9—C8	121.89 (16)	C12—C13—H13	118.2 (12)
N1—C1—C1^i	112.30 (18)	C11—C10—C9	120.00 (18)
N1—C1—H1A	110.9 (9)	C11—C10—H10	123.1 (11)
C1^i—C1—H1A	108.6 (10)	C9—C10—H10	116.9 (11)
N1—C1—H1B	106.3 (10)	C6—C5—C4	118.83 (19)
C1^i—C1—H1B	108.3 (10)	C6—C5—H5	126.4 (13)
H1A—C1—H1B	110.4 (13)	C4—C5—H5	114.8 (13)
N1—C8—C9	113.28 (13)	C12—C11—C10	118.8 (2)
N1—C8—H8A	111.7 (11)	C12—C11—H11	121.5 (12)
C9—C8—H8A	110.5 (10)	C10—C11—H11	119.8 (12)
N1—C8—H8B	107.2 (10)	C5—C6—C7	118.40 (19)
C9—C8—H8B	109.0 (10)	C5—C6—H6	123.4 (11)
H8A—C8—H8B	104.7 (14)	C7—C6—H6	118.2 (11)
N1—C2—C3	111.91 (13)	C11—C12—C13	118.47 (18)
N1—C2—H2A	113.7 (9)	C11—C12—H12	121.6 (12)
C3—C2—H2A	109.2 (10)	C13—C12—H12	119.9 (12)
N1—C2—H2B	107.9 (10)
C7—N2—C3—C4	0.9 (2)	C4—C3—C2—N1	50.3 (2)
C7—N2—C3—C2	−177.2 (1)	N2—C3—C4—C5	−0.5 (3)
C13—N3—C9—C10	0.6 (2)	C2—C3—C4—C5	177.5 (2)
C13—N3—C9—C8	−176.7 (2)	C3—N2—C7—C6	−1.0 (3)
C8—N1—C1—C1^i	−159.6 (2)	C9—N3—C13—C12	0.2 (3)
C2—N1—C1—C1^i	77.1 (2)	N3—C9—C10—C11	−0.6 (3)
C1—N1—C8—C9	76.8 (2)	C8—C9—C10—C11	176.5 (2)
C2—N1—C8—C9	−158.8 (1)	C3—C4—C5—C6	0.2 (3)
N3—C9—C8—N1	−130.8 (1)	C9—C10—C11—C12	−0.1 (3)
C10—C9—C8—N1	52.0 (2)	C4—C5—C6—C7	−0.3 (3)
C8—N1—C2—C3	72.5 (2)	N2—C7—C6—C5	0.7 (3)
C1—N1—C2—C3	−163.9 (1)	C10—C11—C12—C13	0.8 (3)
N2—C3—C2—N1	−131.5 (2)	N3—C13—C12—C11	−0.9 (3)

Symmetry code: (i) −x, −y+1, −z+1.