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

Khalaji, A.D.; Ng, S.W.

doi:10.1107/S1600536808025919

organic compounds

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Volume 64| Part 9| September 2008| Page o1771

doi:10.1107/S1600536808025919

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

Aliakbar Dehno Khalaji ^a and Seik Weng Ng ^b ^*

^aDepartment of Science, Gorgan University of Agricultural Sciences and Natural Resources, Gorgan 49189-43464, Iran, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 11 August 2008; accepted 11 August 2008; online 16 August 2008)

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, $[P \overline 1]$
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) Å³
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[F² > 2σ(F²)] = 0.069
wR(F²) = 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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808025919/xu2448sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808025919/xu2448Isup2.hkl

checkCIF report

Related literature top

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 top

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.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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).

Figures top

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.

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

Crystal data top

C₂₂H₂₄N₂	Z = 2
M_r = 316.43	F(000) = 340
Triclinic, P1	D_x = 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 = 3.2–28.0°
c = 10.202 (2) Å	µ = 0.07 mm⁻¹
α = 88.160 (3)°	T = 100 K
β = 76.865 (2)°	Block, colorless
γ = 78.651 (3)°	0.24 × 0.12 × 0.08 mm
V = 888.3 (3) Å³

Data collection top

Bruker SMART APEX diffractometer	2186 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.023
Graphite monochromator	θ_max = 25.0°, θ_min = 2.1°
ω scans	h = −11→11
4114 measured reflections	k = −11→7
3015 independent reflections	l = −12→12

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.228	H-atom parameters constrained
S = 1.13	w = 1/[σ²(F_o²) + (0.0966P)² + 1.385P] where P = (F_o² + 2F_c²)/3
3015 reflections	(Δ/σ)_max = 0.001
219 parameters	Δρ_max = 0.34 e Å⁻³
0 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₂₂H₂₄N₂	γ = 78.651 (3)°
M_r = 316.43	V = 888.3 (3) Å³
Triclinic, P1	Z = 2
a = 9.524 (2) Å	Mo Kα radiation
b = 9.576 (2) Å	µ = 0.07 mm⁻¹
c = 10.202 (2) Å	T = 100 K
α = 88.160 (3)°	0.24 × 0.12 × 0.08 mm
β = 76.865 (2)°

Data collection top

Bruker SMART APEX diffractometer	2186 reflections with I > 2σ(I)
4114 measured reflections	R_int = 0.023
3015 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.069	0 restraints
wR(F²) = 0.228	H-atom parameters constrained
S = 1.13	Δρ_max = 0.34 e Å⁻³
3015 reflections	Δρ_min = −0.31 e Å⁻³
219 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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 (Å²) top

	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, º) top

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.

Experimental details

Crystal data
Chemical formula	C₂₂H₂₄N₂
M_r	316.43
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	9.524 (2), 9.576 (2), 10.202 (2)
α, β, γ (°)	88.160 (3), 76.865 (2), 78.651 (3)
V (Å³)	888.3 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.24 × 0.12 × 0.08

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	4114, 3015, 2186
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.069, 0.228, 1.13
No. of reflections	3015
No. of parameters	219
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.31

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2008).

Acknowledgements

We thank Gorgan University of Agricultural Sciences and Natural Resources and the University of Malaya for supporting this study.

References

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