4-[4-(n-Decyloxy)benzyl­ideneamino]benzonitrile

In the title compound, C₂₄H₃₀N₂O, the configuration of the azomethine (C=N) bond is E. A C—H...π inter­action also contributes to the stability of the structure. The mol­ecules form infinite layers with an anti­parallel arrangement of the CN groups.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.042
• wR factor = 0.132
• Data-to-parameter ratio = 15.8

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT027_ALERT_3_B _diffrn_reflns_theta_full (too) Low ............      24.97 Deg.

Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.82 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.28 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C5
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C4     -   C24    ...       1.44 Ang.

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: CAD-4 Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: PARST95 (Nardelli, 1995) and PLATON (Spek, 2003).

4-[4-(n-Decyloxy)benzylideneamino]benzonitrile

Crystal data

C24H30N2O	Z = 2
Mr = 362.50	F(000) = 392
Triclinic, P1	Dx = 1.097 Mg m^−3
Hall symbol: -P 1	Melting point: 523 K
a = 8.564 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.571 (2) Å	Cell parameters from 25 reflections
c = 14.114 (3) Å	θ = 6.2–13.5°
α = 101.56 (2)°	µ = 0.07 mm^−1
β = 91.68 (3)°	T = 295 K
γ = 103.69 (2)°	Plate, yellow
V = 1097.6 (6) Å^3	0.4 × 0.3 × 0.1 mm

Data collection

Enraf–Nonius CAD-4 diffractometer	Rint = 0.011
Radiation source: fine-focus sealed tube	θmax = 25.0°, θmin = 2.2°
Graphite monochromator	h = 0→10
ω/2θ scans	k = −11→11
3886 measured reflections	l = −16→16
3859 independent reflections	2 standard reflections every 100 reflections
1960 reflections with I > 2σ(I)	intensity decay: <2%

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.132	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0581P)^2 + 0.0582P] where P = (Fo^2 + 2Fc^2)/3
3853 reflections	(Δ/σ)max < 0.001
244 parameters	Δρmax = 0.11 e Å^−3
0 restraints	Δρmin = −0.15 e Å^−3

Special details

Experimental. The title compound was synthesized by heating 4-decyloxy benzaldehyde with 4-cyano aniline in dry methanol and pyridinum hydrochloride. 4-Decylocy benzaldehyde was obtained by stirring phenol with n-decyloxy chloride in aqueous solution of methylene chloride and benzyltributyl ammonium chloride at room temperature for six hours followed by Reimer-Tiemann reaction to obtain ortho- and para- products of decyloxy benzaldehyde. The para product was separated by column chromatography 4-cyano aniline was obtained from p-nitrobenzoic acid by first reducing nitro into the corresponding amino derivative followed by converting carboxyl group into cyano group.

Geometry. 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.

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
O1	0.10737 (15)	0.73577 (13)	0.52427 (9)	0.0673 (4)
N1	0.8487 (2)	−0.0469 (3)	−0.08978 (14)	0.1108 (8)
N2	0.5411 (2)	0.38058 (17)	0.26221 (11)	0.0665 (4)
C1	0.6056 (2)	0.2945 (2)	0.18759 (13)	0.0630 (5)
C2	0.7279 (2)	0.2336 (2)	0.21210 (14)	0.0674 (5)
H2	0.7654	0.2507	0.2769	0.081*
C3	0.7962 (2)	0.1480 (2)	0.14290 (14)	0.0699 (6)
H3	0.8774	0.1068	0.1612	0.084*
C4	0.7428 (3)	0.1238 (2)	0.04616 (15)	0.0726 (6)
C5	0.6260 (3)	0.1906 (3)	0.02079 (15)	0.0980 (8)
H5	0.5924	0.1780	−0.0443	0.118*
C6	0.5589 (3)	0.2753 (3)	0.09035 (15)	0.0910 (7)
H6	0.4812	0.3201	0.0718	0.109*
C7	0.3930 (3)	0.3813 (2)	0.25258 (13)	0.0663 (5)
H7	0.3305	0.3213	0.1979	0.080*
C8	0.3165 (2)	0.47137 (19)	0.32289 (13)	0.0574 (5)
C9	0.3985 (2)	0.5564 (2)	0.40956 (13)	0.0602 (5)
H9	0.5054	0.5564	0.4235	0.072*
C10	0.3238 (2)	0.64020 (19)	0.47483 (13)	0.0614 (5)
H10	0.3801	0.6945	0.5331	0.074*
C11	0.1660 (2)	0.64530 (19)	0.45542 (13)	0.0559 (5)
C12	0.0813 (2)	0.5602 (2)	0.36999 (14)	0.0652 (5)
H12	−0.0254	0.5606	0.3562	0.078*
C13	0.1574 (2)	0.4742 (2)	0.30519 (14)	0.0669 (5)
H13	0.0999	0.4168	0.2481	0.080*
C14	−0.0511 (2)	0.75415 (19)	0.50652 (14)	0.0624 (5)
H14A	−0.1304	0.6615	0.5019	0.075*
H14B	−0.0594	0.7858	0.4459	0.075*
C15	−0.0816 (2)	0.8678 (2)	0.58897 (14)	0.0626 (5)
H15A	0.0011	0.9584	0.5941	0.075*
H15B	−0.0729	0.8343	0.6489	0.075*
C16	−0.2454 (2)	0.8994 (2)	0.57755 (13)	0.0639 (5)
H16A	−0.2513	0.9382	0.5194	0.077*
H16B	−0.3274	0.8075	0.5683	0.077*
C17	−0.2834 (2)	1.0063 (2)	0.66178 (13)	0.0659 (5)
H17A	−0.2006	1.0978	0.6711	0.079*
H17B	−0.2772	0.9672	0.7197	0.079*
C18	−0.4459 (2)	1.0405 (2)	0.65239 (12)	0.0642 (5)
H18A	−0.4490	1.0880	0.5980	0.077*
H18B	−0.5287	0.9487	0.6378	0.077*
C19	−0.4853 (2)	1.1380 (2)	0.74169 (13)	0.0671 (5)
H19A	−0.4812	1.0901	0.7958	0.080*
H19B	−0.4019	1.2293	0.7561	0.080*
C20	−0.6465 (2)	1.1749 (2)	0.73569 (14)	0.0721 (6)
H20A	−0.7294	1.0840	0.7148	0.086*
H20B	−0.6466	1.2324	0.6864	0.086*
C21	−0.6903 (3)	1.2596 (2)	0.82947 (15)	0.0806 (6)
H21A	−0.6868	1.2034	0.8792	0.097*
H21B	−0.6088	1.3517	0.8493	0.097*
C22	−0.8509 (3)	1.2931 (3)	0.8254 (2)	0.1192 (10)
H22A	−0.9319	1.2015	0.8022	0.143*
H22B	−0.8524	1.3537	0.7780	0.143*
C23	−0.8982 (4)	1.3707 (3)	0.9200 (2)	0.1575 (14)
H23A	−1.0029	1.3878	0.9102	0.236*
H23B	−0.8208	1.4630	0.9431	0.236*
H23C	−0.9010	1.3104	0.9671	0.236*
C24	0.8051 (3)	0.0299 (3)	−0.02849 (16)	0.0863 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0560 (8)	0.0726 (9)	0.0734 (9)	0.0272 (7)	0.0032 (6)	0.0027 (7)
N1	0.0980 (15)	0.1484 (19)	0.0792 (13)	0.0595 (14)	−0.0027 (11)	−0.0248 (13)
N2	0.0680 (11)	0.0733 (11)	0.0599 (10)	0.0275 (9)	0.0099 (8)	0.0059 (8)
C1	0.0599 (12)	0.0690 (12)	0.0586 (13)	0.0193 (10)	0.0068 (10)	0.0060 (10)
C2	0.0631 (13)	0.0786 (13)	0.0569 (12)	0.0191 (11)	0.0042 (10)	0.0042 (10)
C3	0.0607 (13)	0.0828 (14)	0.0661 (13)	0.0243 (11)	0.0066 (10)	0.0078 (11)
C4	0.0655 (13)	0.0851 (15)	0.0619 (13)	0.0242 (11)	0.0077 (10)	−0.0036 (11)
C5	0.1043 (18)	0.144 (2)	0.0531 (13)	0.0646 (18)	−0.0006 (12)	−0.0010 (14)
C6	0.0971 (17)	0.1252 (19)	0.0620 (14)	0.0602 (15)	0.0038 (12)	0.0079 (13)
C7	0.0707 (14)	0.0657 (12)	0.0585 (12)	0.0191 (11)	0.0023 (10)	0.0022 (10)
C8	0.0571 (12)	0.0559 (11)	0.0592 (11)	0.0154 (9)	0.0038 (9)	0.0109 (10)
C9	0.0511 (11)	0.0665 (12)	0.0630 (12)	0.0184 (10)	0.0015 (9)	0.0094 (10)
C10	0.0554 (12)	0.0643 (12)	0.0617 (12)	0.0199 (10)	−0.0004 (9)	0.0015 (10)
C11	0.0532 (12)	0.0529 (11)	0.0634 (12)	0.0184 (9)	0.0048 (9)	0.0102 (10)
C12	0.0536 (12)	0.0685 (12)	0.0738 (13)	0.0212 (10)	−0.0040 (10)	0.0095 (11)
C13	0.0623 (13)	0.0691 (13)	0.0634 (12)	0.0178 (10)	−0.0059 (10)	0.0001 (10)
C14	0.0541 (12)	0.0613 (12)	0.0746 (13)	0.0208 (10)	0.0043 (9)	0.0132 (10)
C15	0.0571 (12)	0.0593 (11)	0.0718 (13)	0.0181 (9)	0.0058 (9)	0.0103 (10)
C16	0.0579 (12)	0.0677 (12)	0.0665 (12)	0.0225 (10)	0.0055 (9)	0.0071 (10)
C17	0.0647 (13)	0.0699 (13)	0.0647 (12)	0.0242 (10)	0.0044 (10)	0.0091 (10)
C18	0.0643 (13)	0.0698 (12)	0.0596 (12)	0.0233 (10)	0.0059 (9)	0.0086 (10)
C19	0.0676 (13)	0.0690 (12)	0.0636 (12)	0.0243 (11)	0.0042 (10)	0.0031 (10)
C20	0.0714 (14)	0.0809 (14)	0.0680 (13)	0.0301 (11)	0.0115 (10)	0.0112 (11)
C21	0.0840 (16)	0.0798 (14)	0.0799 (15)	0.0325 (12)	0.0177 (12)	0.0054 (12)
C22	0.105 (2)	0.143 (2)	0.130 (2)	0.0734 (19)	0.0340 (17)	0.0224 (19)
C23	0.149 (3)	0.139 (3)	0.188 (3)	0.063 (2)	0.086 (2)	−0.001 (2)
C24	0.0745 (15)	0.1109 (18)	0.0682 (14)	0.0343 (14)	0.0011 (12)	−0.0062 (14)

Geometric parameters (Å, º)

O1—C11	1.357 (2)	C14—H14A	0.9700
O1—C14	1.431 (2)	C14—H14B	0.9700
N1—C24	1.149 (2)	C15—C16	1.514 (2)
N2—C7	1.274 (2)	C15—H15A	0.9700
N2—C1	1.412 (2)	C15—H15B	0.9700
C1—C2	1.381 (3)	C16—C17	1.503 (2)
C1—C6	1.381 (3)	C16—H16A	0.9700
C2—C3	1.381 (2)	C16—H16B	0.9700
C2—H2	0.9300	C17—C18	1.512 (2)
C3—C4	1.383 (3)	C17—H17A	0.9700
C3—H3	0.9300	C17—H17B	0.9700
C4—C5	1.382 (3)	C18—C19	1.508 (2)
C4—C24	1.443 (3)	C18—H18A	0.9700
C5—C6	1.373 (3)	C18—H18B	0.9700
C5—H5	0.9300	C19—C20	1.508 (2)
C6—H6	0.9300	C19—H19A	0.9700
C7—C8	1.456 (2)	C19—H19B	0.9700
C7—H7	0.9300	C20—C21	1.514 (2)
C8—C13	1.385 (2)	C20—H20A	0.9700
C8—C9	1.390 (2)	C20—H20B	0.9700
C9—C10	1.372 (2)	C21—C22	1.486 (3)
C9—H9	0.9300	C21—H21A	0.9700
C10—C11	1.386 (2)	C21—H21B	0.9700
C10—H10	0.9300	C22—C23	1.509 (3)
C11—C12	1.385 (2)	C22—H22A	0.9700
C12—C13	1.387 (2)	C22—H22B	0.9700
C12—H12	0.9300	C23—H23A	0.9600
C13—H13	0.9300	C23—H23B	0.9600
C14—C15	1.500 (2)	C23—H23C	0.9600
C11—O1—C14	118.72 (15)	C16—C15—H15B	108.9
C7—N2—C1	118.90 (17)	H15A—C15—H15B	107.7
C2—C1—C6	118.03 (18)	C17—C16—C15	114.54 (16)
C2—C1—N2	118.67 (17)	C17—C16—H16A	108.6
C6—C1—N2	123.18 (19)	C15—C16—H16A	108.6
C1—C2—C3	121.76 (19)	C17—C16—H16B	108.6
C1—C2—H2	119.1	C15—C16—H16B	108.6
C3—C2—H2	119.1	H16A—C16—H16B	107.6
C2—C3—C4	119.4 (2)	C16—C17—C18	115.79 (16)
C2—C3—H3	120.3	C16—C17—H17A	108.3
C4—C3—H3	120.3	C18—C17—H17A	108.3
C5—C4—C3	119.00 (19)	C16—C17—H17B	108.3
C5—C4—C24	119.4 (2)	C18—C17—H17B	108.3
C3—C4—C24	121.6 (2)	H17A—C17—H17B	107.4
C6—C5—C4	120.9 (2)	C19—C18—C17	114.17 (15)
C6—C5—H5	119.5	C19—C18—H18A	108.7
C4—C5—H5	119.5	C17—C18—H18A	108.7
C5—C6—C1	120.7 (2)	C19—C18—H18B	108.7
C5—C6—H6	119.6	C17—C18—H18B	108.7
C1—C6—H6	119.6	H18A—C18—H18B	107.6
N2—C7—C8	123.32 (18)	C20—C19—C18	116.04 (16)
N2—C7—H7	118.3	C20—C19—H19A	108.3
C8—C7—H7	118.3	C18—C19—H19A	108.3
C13—C8—C9	117.69 (17)	C20—C19—H19B	108.3
C13—C8—C7	120.48 (18)	C18—C19—H19B	108.3
C9—C8—C7	121.83 (18)	H19A—C19—H19B	107.4
C10—C9—C8	120.80 (18)	C19—C20—C21	114.91 (17)
C10—C9—H9	119.6	C19—C20—H20A	108.5
C8—C9—H9	119.6	C21—C20—H20A	108.5
C9—C10—C11	121.10 (18)	C19—C20—H20B	108.5
C9—C10—H10	119.4	C21—C20—H20B	108.5
C11—C10—H10	119.4	H20A—C20—H20B	107.5
O1—C11—C12	125.45 (17)	C22—C21—C20	115.49 (19)
O1—C11—C10	115.50 (17)	C22—C21—H21A	108.4
C12—C11—C10	119.04 (17)	C20—C21—H21A	108.4
C11—C12—C13	119.30 (18)	C22—C21—H21B	108.4
C11—C12—H12	120.3	C20—C21—H21B	108.4
C13—C12—H12	120.3	H21A—C21—H21B	107.5
C8—C13—C12	122.02 (18)	C21—C22—C23	115.5 (2)
C8—C13—H13	119.0	C21—C22—H22A	108.4
C12—C13—H13	119.0	C23—C22—H22A	108.4
O1—C14—C15	108.26 (15)	C21—C22—H22B	108.4
O1—C14—H14A	110.0	C23—C22—H22B	108.4
C15—C14—H14A	110.0	H22A—C22—H22B	107.5
O1—C14—H14B	110.0	C22—C23—H23A	109.5
C15—C14—H14B	110.0	C22—C23—H23B	109.5
H14A—C14—H14B	108.4	H23A—C23—H23B	109.5
C14—C15—C16	113.31 (16)	C22—C23—H23C	109.5
C14—C15—H15A	108.9	H23A—C23—H23C	109.5
C16—C15—H15A	108.9	H23B—C23—H23C	109.5
C14—C15—H15B	108.9	N1—C24—C4	177.3 (2)
C7—N2—C1—C2	−148.27 (19)	C7—N2—C1—C6	35.7 (3)