N,N′-Bis[(E)-2-Benzyl­idenepropylidene]ethane-1,2-diamine

Abstract

The two independent mol­ecules in the asymmetric unit of the title Schiff base, C₂₂H₂₄N₂, lie across centers of inversion. The C=N double bonds are in a trans configuration.

Related literature

There are many examples of similar Schiff bases in the current (2008) Cambrige Structural Database; for example, see: Khalaji et al. (2007 ▶). For the structure of bis­[(E)-3-phenyl­propen-1-al]-1,2-diimino­ethane, see: Khalaji & Weil (2007 ▶).

Experimental

Crystal data

• C₂₂H₂₄N₂

• M _r = 316.43

• Triclinic,

• a = 9.524 (2) Å

• b = 9.576 (2) Å

• c = 10.202 (2) Å

• α = 88.160 (3)°

• β = 76.865 (2)°

• γ = 78.651 (3)°

• V = 888.3 (3) ų

• Z = 2

• Mo Kα radiation

• μ = 0.07 mm⁻¹

• T = 100 (2) K

• 0.24 × 0.12 × 0.08 mm

Data collection

• Bruker SMART APEX diffractometer

• Absorption correction: none

• 4114 measured reflections

• 3015 independent reflections

• 2186 reflections with I > 2σ(I)

• R _int = 0.023

Refinement

• R[F ² > 2σ(F ²)] = 0.069

• wR(F ²) = 0.228

• S = 1.13

• 3015 reflections

• 219 parameters

• H-atom parameters constrained

• Δρ_max = 0.34 e Å⁻³

• Δρ_min = −0.30 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2008 ▶).

Supplementary Material

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

supplementary crystallographic information

Comment

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Experimental

Ethylenediamine (1 mmol, 60 mg) and α-methylcinnamaldehyde (2 mmol, 292 mg) were dissolved in methanol (10 ml) to give a colorless solution. Slow evaporation of the solvent yielded colorless crystals in about 85% yield.

Refinement

Carbon-bound H-atoms were placed in calculated positions (C—H 0.95 to 0.98 Å) and were included in the refinement in the riding model approximation, with U(H) fixed at 1.2 to 1.5U(C).

Figures

Fig. 1.

Thermal ellipsoid plot (Barbour, 2001) of the two independent molecules of the title compound; probability ellipsoids are set at the 70% level, and H atoms are drawn as spheres of arbitrary radius. The two molecules lie about centers of inversion.

Crystal data

C22H24N2	Z = 2
Mr = 316.43	F000 = 340
Triclinic, P1	Dx = 1.183 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 9.524 (2) Å	Cell parameters from 1031 reflections
b = 9.576 (2) Å	θ = 3.2–28.0º
c = 10.202 (2) Å	µ = 0.07 mm−1
α = 88.160 (3)º	T = 100 (2) K
β = 76.865 (2)º	Block, colorless
γ = 78.651 (3)º	0.24 × 0.12 × 0.08 mm
V = 888.3 (3) Å3

Data collection

Bruker SMART APEX diffractometer	2186 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.023
Monochromator: graphite	θmax = 25.0º
T = 100(2) K	θmin = 2.1º
ω scans	h = −11→11
Absorption correction: None	k = −11→7
4114 measured reflections	l = −12→12
3015 independent reflections

Refinement

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.069	H-atom parameters constrained
wR(F2) = 0.228	w = 1/[σ2(Fo2) + (0.0966P)2 + 1.385P] where P = (Fo2 + 2Fc2)/3
S = 1.13	(Δ/σ)max = 0.001
3015 reflections	Δρmax = 0.34 e Å−3
219 parameters	Δρmin = −0.30 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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

	x	y	z	Uiso*/Ueq
N1	0.3982 (3)	1.1256 (3)	0.1398 (3)	0.0221 (7)
N2	0.3642 (3)	0.5970 (3)	0.1443 (3)	0.0220 (7)
C1	0.1158 (4)	1.3426 (4)	0.6498 (4)	0.0242 (8)
H1	0.0674	1.3700	0.5785	0.029*
C2	0.0423 (4)	1.3777 (4)	0.7810 (4)	0.0268 (9)
H2	−0.0567	1.4279	0.7993	0.032*
C3	0.1114 (4)	1.3405 (4)	0.8862 (4)	0.0238 (8)
H3	0.0597	1.3646	0.9762	0.029*
C4	0.2550 (4)	1.2685 (4)	0.8602 (4)	0.0238 (8)
H4	0.3026	1.2428	0.9322	0.029*
C5	0.3297 (4)	1.2335 (4)	0.7291 (3)	0.0218 (8)
H5	0.4296	1.1860	0.7118	0.026*
C6	0.2613 (4)	1.2668 (4)	0.6210 (3)	0.0209 (8)
C7	0.3478 (4)	1.2169 (4)	0.4872 (3)	0.0211 (8)
H7	0.4501	1.1871	0.4819	0.025*
C8	0.3067 (4)	1.2062 (4)	0.3699 (3)	0.0198 (8)
C9	0.1543 (4)	1.2473 (5)	0.3469 (4)	0.0358 (10)
H9A	0.0849	1.2137	0.4217	0.054*
H9B	0.1502	1.2039	0.2625	0.054*
H9C	0.1279	1.3512	0.3415	0.054*
C10	0.4227 (4)	1.1443 (4)	0.2552 (3)	0.0209 (8)
H10	0.5204	1.1169	0.2671	0.025*
C11	0.5216 (4)	1.0601 (4)	0.0345 (3)	0.0224 (8)
H11A	0.6070	1.0211	0.0738	0.027*
H11B	0.5500	1.1325	−0.0326	0.027*
C12	0.1872 (4)	0.8841 (4)	0.6385 (4)	0.0234 (8)
H12	0.1826	0.9391	0.5599	0.028*
C13	0.1387 (4)	0.9502 (4)	0.7643 (4)	0.0235 (8)
H13	0.1002	1.0497	0.7709	0.028*
C14	0.1461 (4)	0.8727 (4)	0.8798 (4)	0.0252 (8)
H14	0.1117	0.9184	0.9656	0.030*
C15	0.2040 (4)	0.7277 (4)	0.8698 (4)	0.0238 (8)
H15	0.2112	0.6740	0.9488	0.029*
C16	0.2510 (4)	0.6617 (4)	0.7450 (4)	0.0224 (8)
H16	0.2901	0.5622	0.7394	0.027*
C17	0.2427 (3)	0.7372 (4)	0.6261 (3)	0.0188 (8)
C18	0.2977 (4)	0.6565 (4)	0.4993 (4)	0.0210 (8)
H18	0.3495	0.5626	0.5085	0.025*
C19	0.2885 (4)	0.6906 (4)	0.3718 (3)	0.0201 (8)
C20	0.2131 (4)	0.8296 (4)	0.3247 (4)	0.0260 (9)
H20A	0.1151	0.8581	0.3833	0.039*
H20B	0.2041	0.8184	0.2320	0.039*
H20C	0.2711	0.9028	0.3282	0.039*
C21	0.3610 (4)	0.5804 (4)	0.2695 (3)	0.0207 (8)
H21	0.4084	0.4915	0.2977	0.025*
C22	0.4398 (4)	0.4776 (4)	0.0556 (3)	0.0245 (8)
H22A	0.3687	0.4421	0.0145	0.029*
H22B	0.4845	0.3993	0.1079	0.029*

Atomic displacement parameters (Ų)

	U11	U22	U33	U12	U13	U23
N1	0.0217 (15)	0.0204 (16)	0.0237 (17)	−0.0038 (12)	−0.0043 (13)	−0.0017 (12)
N2	0.0225 (15)	0.0213 (16)	0.0224 (17)	−0.0058 (12)	−0.0041 (12)	0.0005 (12)
C1	0.0238 (18)	0.026 (2)	0.0222 (19)	−0.0025 (15)	−0.0076 (15)	0.0024 (15)
C2	0.0238 (19)	0.027 (2)	0.028 (2)	−0.0021 (16)	−0.0043 (16)	−0.0027 (16)
C3	0.0293 (19)	0.0191 (19)	0.0221 (19)	−0.0049 (15)	−0.0035 (15)	−0.0022 (15)
C4	0.030 (2)	0.0163 (18)	0.027 (2)	−0.0048 (15)	−0.0112 (16)	0.0010 (15)
C5	0.0228 (18)	0.0181 (18)	0.026 (2)	−0.0040 (15)	−0.0085 (15)	0.0012 (15)
C6	0.0238 (18)	0.0178 (18)	0.0226 (19)	−0.0077 (14)	−0.0054 (15)	0.0012 (14)
C7	0.0198 (17)	0.0186 (18)	0.0239 (19)	−0.0034 (14)	−0.0031 (15)	−0.0003 (15)
C8	0.0233 (18)	0.0190 (18)	0.0191 (18)	−0.0075 (15)	−0.0062 (15)	0.0033 (14)
C9	0.028 (2)	0.053 (3)	0.025 (2)	0.0003 (19)	−0.0093 (17)	−0.0110 (19)
C10	0.0200 (17)	0.0176 (18)	0.026 (2)	−0.0054 (14)	−0.0064 (15)	0.0046 (14)
C11	0.0220 (18)	0.026 (2)	0.0196 (18)	−0.0063 (15)	−0.0036 (15)	0.0001 (15)
C12	0.0253 (19)	0.023 (2)	0.026 (2)	−0.0094 (15)	−0.0108 (16)	0.0056 (15)
C13	0.0176 (17)	0.0210 (19)	0.031 (2)	−0.0011 (14)	−0.0054 (15)	−0.0033 (15)
C14	0.0189 (18)	0.030 (2)	0.0243 (19)	−0.0042 (15)	0.0006 (15)	−0.0064 (16)
C15	0.0227 (18)	0.030 (2)	0.0179 (18)	−0.0043 (16)	−0.0046 (15)	0.0036 (15)
C16	0.0208 (17)	0.0196 (19)	0.027 (2)	−0.0033 (15)	−0.0076 (15)	0.0042 (15)
C17	0.0143 (16)	0.0236 (19)	0.0185 (18)	−0.0059 (14)	−0.0021 (13)	0.0023 (14)
C18	0.0196 (17)	0.0153 (18)	0.028 (2)	−0.0020 (14)	−0.0057 (15)	0.0013 (14)
C19	0.0190 (17)	0.0210 (19)	0.0215 (19)	−0.0072 (14)	−0.0043 (14)	0.0018 (14)
C20	0.028 (2)	0.0214 (19)	0.025 (2)	0.0013 (16)	−0.0037 (16)	0.0007 (16)
C21	0.0236 (18)	0.0176 (18)	0.0222 (19)	−0.0061 (15)	−0.0059 (14)	0.0014 (14)
C22	0.031 (2)	0.0207 (19)	0.0220 (19)	−0.0058 (16)	−0.0067 (16)	−0.0025 (15)

Geometric parameters (Å, °)

N1—C10	1.276 (5)	C11—H11A	0.9900
N1—C11	1.452 (5)	C11—H11B	0.9900
N2—C21	1.276 (5)	C12—C13	1.389 (5)
N2—C22	1.446 (5)	C12—C17	1.401 (5)
C1—C2	1.380 (5)	C12—H12	0.9500
C1—C6	1.403 (5)	C13—C14	1.380 (5)
C1—H1	0.9500	C13—H13	0.9500
C2—C3	1.384 (5)	C14—C15	1.388 (5)
C2—H2	0.9500	C14—H14	0.9500
C3—C4	1.375 (5)	C15—C16	1.380 (5)
C3—H3	0.9500	C15—H15	0.9500
C4—C5	1.382 (5)	C16—C17	1.401 (5)
C4—H4	0.9500	C16—H16	0.9500
C5—C6	1.401 (5)	C17—C18	1.464 (5)
C5—H5	0.9500	C18—C19	1.349 (5)
C6—C7	1.465 (5)	C18—H18	0.9500
C7—C8	1.354 (5)	C19—C21	1.462 (5)
C7—H7	0.9500	C19—C20	1.502 (5)
C8—C10	1.463 (5)	C20—H20A	0.9800
C8—C9	1.497 (5)	C20—H20B	0.9800
C9—H9A	0.9800	C20—H20C	0.9800
C9—H9B	0.9800	C21—H21	0.9500
C9—H9C	0.9800	C22—C22ii	1.534 (7)
C10—H10	0.9500	C22—H22A	0.9900
C11—C11i	1.536 (7)	C22—H22B	0.9900
C10—N1—C11	117.7 (3)	H11A—C11—H11B	108.2
C21—N2—C22	117.0 (3)	C13—C12—C17	120.8 (3)
C2—C1—C6	120.5 (3)	C13—C12—H12	119.6
C2—C1—H1	119.8	C17—C12—H12	119.6
C6—C1—H1	119.8	C14—C13—C12	120.6 (3)
C1—C2—C3	120.7 (3)	C14—C13—H13	119.7
C1—C2—H2	119.7	C12—C13—H13	119.7
C3—C2—H2	119.7	C13—C14—C15	119.6 (3)
C4—C3—C2	119.9 (3)	C13—C14—H14	120.2
C4—C3—H3	120.0	C15—C14—H14	120.2
C2—C3—H3	120.0	C16—C15—C14	119.8 (3)
C3—C4—C5	119.8 (3)	C16—C15—H15	120.1
C3—C4—H4	120.1	C14—C15—H15	120.1
C5—C4—H4	120.1	C15—C16—C17	121.8 (3)
C4—C5—C6	121.4 (3)	C15—C16—H16	119.1
C4—C5—H5	119.3	C17—C16—H16	119.1
C6—C5—H5	119.3	C12—C17—C16	117.3 (3)
C5—C6—C1	117.6 (3)	C12—C17—C18	125.6 (3)
C5—C6—C7	116.9 (3)	C16—C17—C18	117.1 (3)
C1—C6—C7	125.5 (3)	C19—C18—C17	132.0 (3)
C8—C7—C6	131.0 (3)	C19—C18—H18	114.0
C8—C7—H7	114.5	C17—C18—H18	114.0
C6—C7—H7	114.5	C18—C19—C21	116.0 (3)
C7—C8—C10	116.5 (3)	C18—C19—C20	126.8 (3)
C7—C8—C9	126.6 (3)	C21—C19—C20	117.2 (3)
C10—C8—C9	116.9 (3)	C19—C20—H20A	109.5
C8—C9—H9A	109.5	C19—C20—H20B	109.5
C8—C9—H9B	109.5	H20A—C20—H20B	109.5
H9A—C9—H9B	109.5	C19—C20—H20C	109.5
C8—C9—H9C	109.5	H20A—C20—H20C	109.5
H9A—C9—H9C	109.5	H20B—C20—H20C	109.5
H9B—C9—H9C	109.5	N2—C21—C19	123.5 (3)
N1—C10—C8	122.7 (3)	N2—C21—H21	118.2
N1—C10—H10	118.6	C19—C21—H21	118.2
C8—C10—H10	118.6	N2—C22—C22ii	110.4 (4)
N1—C11—C11i	109.5 (3)	N2—C22—H22A	109.6
N1—C11—H11A	109.8	C22ii—C22—H22A	109.6
C11i—C11—H11A	109.8	N2—C22—H22B	109.6
N1—C11—H11B	109.8	C22ii—C22—H22B	109.6
C11i—C11—H11B	109.8	H22A—C22—H22B	108.1
C6—C1—C2—C3	0.9 (6)	C17—C12—C13—C14	0.8 (5)
C1—C2—C3—C4	0.4 (6)	C12—C13—C14—C15	0.7 (5)
C2—C3—C4—C5	0.0 (5)	C13—C14—C15—C16	−1.2 (5)
C3—C4—C5—C6	−1.6 (5)	C14—C15—C16—C17	0.2 (5)
C4—C5—C6—C1	2.8 (5)	C13—C12—C17—C16	−1.8 (5)
C4—C5—C6—C7	−176.2 (3)	C13—C12—C17—C18	−179.5 (3)
C2—C1—C6—C5	−2.4 (5)	C15—C16—C17—C12	1.3 (5)
C2—C1—C6—C7	176.5 (3)	C15—C16—C17—C18	179.2 (3)
C5—C6—C7—C8	165.1 (4)	C12—C17—C18—C19	−12.3 (6)
C1—C6—C7—C8	−13.8 (6)	C16—C17—C18—C19	169.9 (4)
C6—C7—C8—C10	−177.0 (3)	C17—C18—C19—C21	178.9 (3)
C6—C7—C8—C9	1.1 (6)	C17—C18—C19—C20	−0.6 (6)
C11—N1—C10—C8	−178.6 (3)	C22—N2—C21—C19	−179.8 (3)
C7—C8—C10—N1	178.6 (3)	C18—C19—C21—N2	−178.9 (3)
C9—C8—C10—N1	0.2 (5)	C20—C19—C21—N2	0.6 (5)
C10—N1—C11—C11i	131.7 (4)	C21—N2—C22—C22ii	−124.0 (4)

Symmetry codes: (i) −x+1, −y+2, −z; (ii) −x+1, −y+1, −z.