2,6-Diisopropyl-N-[(Z)-quinolin-2-yl­methyl­idene]aniline

Sood, A.; Räisänen, M.T.; Ahlgrén, M.; Leskelä, M.; Repo, T.

doi:10.1107/S1600536807044947

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2,6-Diisopropyl-N-[(Z)-quinolin-2-ylmethylidene]aniline

A. Sood, M. T. Räisänen, M. Ahlgrén, M. Leskelä and T. Repo

In the title compound, C₂₂H₂₄N₂, all bond lengths and angles are within normal ranges. The molecule is in a non-planar conformation, the dihedral angle between the two aromatic ring systems being 55.01 (8)°. The molecular packing is accomplished by a weak intermolecular C—H

N hydrogen bond.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807044947/bt2509sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807044947/bt2509Isup2.hkl Contains datablock I

CCDC reference: 663786

checkCIF report

Key indicators

Single-crystal X-ray study
T = 120 K
Mean (C-C) = 0.003 Å
R factor = 0.053
wR factor = 0.116
Data-to-parameter ratio = 15.3

checkCIF/PLATON results

No syntax errors found



Alert level C
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.141
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.14
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.53 Ratio

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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

Comment top

The title compound was prepared as a ligand for metal complexes to be studied as catalysts for ethene polymerization. Its structure is a typical example of N-aryl Schiff base ligand as it has adopted a non-planar conformation (Fig. 1) and all the bond lengths and angles are within normal ranges (Räisänen, Elo et al., 2007; Räisänen Leskelä, & Repo 2007). The N-aryl substituent is twisted along the C—N axis as the C10—N2—C11—C16 torsion angle is 64.9 (3)° whereas the other aromatic ring is practically in plane with the imine bond as the N2—C10—C9—C8 angle deviates from zero only by -9.2 (3)°. The molecular packing of the compound is facilitated by intermolecular C—H···N hydrogen bonds (H···N distance of 2.61 Å) which fall in the range of weak hydrogen bonds (Alshahateet et al., 2004).

Related literature top

For related literature, see: Yliheikkilä et al. (2007); Räisänen, Elo et al., (2007) Räisänen, Leskelä & Repo (2007); Alshahateet et al. (2004); Kottke & Stalke (1993).

Experimental top

The title compound was synthesized (Yliheikkilä et al., 2007) by refluxing 2,6-diisopropylaniline (1.6 g, 9.1 mmol) and 2-quinolinecarboxaldehyde (1.3 g, 7.8 mmol) in ethanol (40 ml) for 20 min. The solvent was removed and raw product was purified by a column chromatography on basic alumina using pentane/ethyl acetate (3:1) eluent. Recrystallization from n-pentane yielded yellow crystals. The pale yellow crystals suitable for X-ray analysis were obtained from acetone.

Structure description top

For related literature, see: Yliheikkilä et al. (2007); Räisänen, Elo et al., (2007) Räisänen, Leskelä & Repo (2007); Alshahateet et al. (2004); Kottke & Stalke (1993).

Computing details top

Data collection: COLLECT (Nonius, 1997); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top

Fig. 1. Perspective view of the title compound with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.

2,6-Diisopropyl-N-[(Z)-quinolin-2-ylmethylidene]aniline top

Crystal data top

C₂₂H₂₄N₂	Z = 4
M_r = 316.43	F(000) = 680
Monoclinic, P2₁/c	D_x = 1.159 Mg m⁻³
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 13.811 (3) Å	θ = 2.9–25.5°
b = 10.971 (2) Å	µ = 0.07 mm⁻¹
c = 11.995 (2) Å	T = 120 K
β = 93.88 (3)°	Block, yellow
V = 1813.3 (6) Å³	0.30 × 0.30 × 0.25 mm

Data collection top

Nonius KappaCCD area-detector diffractometer	3384 independent reflections
Radiation source: fine-focus sealed tube	1994 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.141
CCD scans	θ_max = 25.5°, θ_min = 2.9°
Absorption correction: multi-scan (XPREP in SHELXTL; Bruker, 1998)	h = −16→16
T_min = 0.980, T_max = 0.983	k = −13→13
29862 measured reflections	l = −14→14

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.116	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.05P)²] where P = (F_o² + 2F_c²)/3
3384 reflections	(Δ/σ)_max < 0.001
221 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₂₂H₂₄N₂	V = 1813.3 (6) Å³
M_r = 316.43	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.811 (3) Å	µ = 0.07 mm⁻¹
b = 10.971 (2) Å	T = 120 K
c = 11.995 (2) Å	0.30 × 0.30 × 0.25 mm
β = 93.88 (3)°

Data collection top

Nonius KappaCCD area-detector diffractometer	3384 independent reflections
Absorption correction: multi-scan (XPREP in SHELXTL; Bruker, 1998)	1994 reflections with I > 2σ(I)
T_min = 0.980, T_max = 0.983	R_int = 0.141
29862 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.116	H-atom parameters constrained
S = 1.06	Δρ_max = 0.18 e Å⁻³
3384 reflections	Δρ_min = −0.19 e Å⁻³
221 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
N1	0.33403 (11)	0.31501 (15)	0.32844 (14)	0.0198 (4)
N2	0.17009 (12)	0.55989 (15)	0.28608 (14)	0.0221 (4)
C1	0.38589 (14)	0.23119 (17)	0.27262 (17)	0.0181 (5)
C2	0.45110 (15)	0.15362 (19)	0.33471 (19)	0.0258 (5)
H2	0.4581	0.1603	0.4138	0.031*
C3	0.50408 (15)	0.06922 (19)	0.28154 (19)	0.0285 (6)
H3	0.5480	0.0179	0.3240	0.034*
C4	0.49432 (15)	0.0576 (2)	0.16481 (19)	0.0296 (6)
H4	0.5315	−0.0018	0.1290	0.036*
C5	0.43210 (15)	0.13036 (19)	0.10256 (19)	0.0268 (5)
H5	0.4259	0.1213	0.0236	0.032*
C6	0.37635 (13)	0.21976 (18)	0.15456 (17)	0.0187 (5)
C7	0.31029 (14)	0.29851 (18)	0.09469 (18)	0.0227 (5)
H7	0.3014	0.2931	0.0156	0.027*
C8	0.25974 (14)	0.38189 (18)	0.15135 (17)	0.0199 (5)
H8	0.2155	0.4358	0.1123	0.024*
C9	0.27386 (14)	0.38728 (18)	0.26879 (17)	0.0188 (5)
C10	0.22059 (14)	0.47578 (18)	0.33397 (18)	0.0211 (5)
H10	0.2241	0.4698	0.4132	0.025*
C11	0.12220 (14)	0.64621 (18)	0.35299 (17)	0.0199 (5)
C12	0.02034 (15)	0.64969 (18)	0.33829 (17)	0.0201 (5)
C13	−0.02806 (16)	0.73603 (19)	0.39868 (19)	0.0268 (5)
H13	−0.0969	0.7395	0.3911	0.032*
C14	0.02217 (16)	0.81686 (19)	0.46951 (19)	0.0295 (6)
H14	−0.0122	0.8757	0.5095	0.035*
C15	0.12161 (16)	0.81238 (19)	0.48227 (18)	0.0274 (6)
H15	0.1552	0.8683	0.5315	0.033*
C16	0.17470 (15)	0.72720 (18)	0.42437 (17)	0.0236 (5)
C17	−0.03429 (14)	0.55741 (18)	0.26433 (18)	0.0239 (5)
H17	0.0083	0.5350	0.2033	0.029*
C18	−0.12959 (15)	0.6060 (2)	0.2089 (2)	0.0353 (6)
H18A	−0.1767	0.6169	0.2656	0.053*
H18B	−0.1553	0.5477	0.1525	0.053*
H18C	−0.1179	0.6844	0.1732	0.053*
C19	−0.05266 (17)	0.4411 (2)	0.3303 (2)	0.0366 (6)
H19A	0.0094	0.4072	0.3601	0.055*
H19B	−0.0862	0.3812	0.2808	0.055*
H19C	−0.0930	0.4603	0.3921	0.055*
C20	0.28494 (15)	0.7276 (2)	0.44076 (19)	0.0303 (6)
H20	0.3102	0.6653	0.3892	0.036*
C21	0.31763 (18)	0.6906 (2)	0.5603 (2)	0.0457 (7)
H21A	0.2943	0.7507	0.6126	0.069*
H21B	0.3887	0.6870	0.5683	0.069*
H21C	0.2908	0.6103	0.5765	0.069*
C22	0.32809 (17)	0.8514 (2)	0.4114 (2)	0.0411 (7)
H22A	0.3058	0.8735	0.3347	0.062*
H22B	0.3991	0.8461	0.4174	0.062*
H22C	0.3069	0.9135	0.4631	0.062*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0197 (9)	0.0174 (9)	0.0222 (10)	0.0002 (8)	0.0019 (8)	−0.0019 (8)
N2	0.0209 (10)	0.0195 (10)	0.0255 (11)	0.0002 (8)	0.0000 (8)	−0.0019 (8)
C1	0.0162 (10)	0.0149 (11)	0.0232 (12)	−0.0019 (9)	0.0016 (9)	−0.0001 (10)
C2	0.0258 (12)	0.0271 (13)	0.0242 (13)	0.0020 (10)	−0.0003 (10)	0.0001 (11)
C3	0.0246 (12)	0.0252 (13)	0.0351 (15)	0.0086 (10)	−0.0015 (11)	0.0012 (11)
C4	0.0283 (13)	0.0273 (13)	0.0334 (15)	0.0071 (11)	0.0041 (11)	−0.0069 (11)
C5	0.0283 (13)	0.0263 (13)	0.0261 (13)	0.0040 (10)	0.0028 (11)	−0.0051 (11)
C6	0.0192 (11)	0.0148 (11)	0.0222 (13)	−0.0031 (9)	0.0014 (10)	−0.0013 (9)
C7	0.0235 (11)	0.0246 (12)	0.0196 (12)	−0.0025 (10)	−0.0009 (10)	0.0020 (10)
C8	0.0197 (11)	0.0180 (12)	0.0218 (12)	0.0008 (9)	0.0007 (10)	0.0012 (10)
C9	0.0187 (11)	0.0148 (11)	0.0227 (13)	0.0001 (9)	−0.0003 (10)	0.0012 (10)
C10	0.0220 (11)	0.0197 (12)	0.0218 (12)	−0.0007 (10)	0.0026 (10)	−0.0014 (10)
C11	0.0246 (12)	0.0135 (11)	0.0218 (12)	0.0039 (9)	0.0037 (10)	−0.0006 (9)
C12	0.0224 (11)	0.0163 (11)	0.0216 (12)	0.0022 (9)	0.0025 (10)	0.0027 (10)
C13	0.0236 (12)	0.0234 (12)	0.0333 (14)	0.0038 (10)	0.0022 (11)	−0.0014 (11)
C14	0.0340 (14)	0.0187 (12)	0.0364 (15)	0.0064 (11)	0.0078 (11)	−0.0064 (11)
C15	0.0355 (14)	0.0177 (12)	0.0286 (13)	0.0017 (10)	0.0001 (11)	−0.0068 (10)
C16	0.0268 (12)	0.0180 (11)	0.0258 (13)	−0.0004 (10)	−0.0005 (10)	0.0010 (10)
C17	0.0236 (12)	0.0217 (12)	0.0266 (13)	0.0006 (10)	0.0025 (10)	−0.0035 (10)
C18	0.0278 (13)	0.0379 (15)	0.0396 (16)	0.0019 (11)	−0.0023 (12)	−0.0067 (12)
C19	0.0426 (14)	0.0249 (13)	0.0422 (16)	−0.0066 (11)	0.0027 (12)	−0.0034 (12)
C20	0.0270 (12)	0.0246 (13)	0.0387 (15)	0.0000 (10)	−0.0028 (11)	−0.0063 (11)
C21	0.0402 (15)	0.0378 (15)	0.0565 (19)	−0.0018 (13)	−0.0151 (13)	0.0062 (14)
C22	0.0322 (14)	0.0359 (15)	0.0551 (18)	−0.0058 (11)	0.0022 (13)	−0.0027 (13)

Geometric parameters (Å, º) top

N1—C9	1.323 (2)	C13—C14	1.382 (3)
N1—C1	1.368 (2)	C13—H13	0.9500
N2—C10	1.270 (2)	C14—C15	1.372 (3)
N2—C11	1.432 (2)	C14—H14	0.9500
C1—C2	1.414 (3)	C15—C16	1.401 (3)
C1—C6	1.419 (3)	C15—H15	0.9500
C2—C3	1.365 (3)	C16—C20	1.522 (3)
C2—H2	0.9500	C17—C18	1.530 (3)
C3—C4	1.403 (3)	C17—C19	1.532 (3)
C3—H3	0.9500	C17—H17	1.0000
C4—C5	1.359 (3)	C18—H18A	0.9800
C4—H4	0.9500	C18—H18B	0.9800
C5—C6	1.417 (3)	C18—H18C	0.9800
C5—H5	0.9500	C19—H19A	0.9800
C6—C7	1.416 (3)	C19—H19B	0.9800
C7—C8	1.360 (3)	C19—H19C	0.9800
C7—H7	0.9500	C20—C21	1.528 (3)
C8—C9	1.410 (3)	C20—C22	1.534 (3)
C8—H8	0.9500	C20—H20	1.0000
C9—C10	1.474 (3)	C21—H21A	0.9800
C10—H10	0.9500	C21—H21B	0.9800
C11—C16	1.402 (3)	C21—H21C	0.9800
C11—C12	1.406 (3)	C22—H22A	0.9800
C12—C13	1.391 (3)	C22—H22B	0.9800
C12—C17	1.514 (3)	C22—H22C	0.9800

C9—N1—C1	117.94 (17)	C13—C14—H14	119.9
C10—N2—C11	119.16 (18)	C14—C15—C16	121.5 (2)
N1—C1—C2	118.85 (19)	C14—C15—H15	119.3
N1—C1—C6	122.11 (18)	C16—C15—H15	119.3
C2—C1—C6	119.04 (18)	C15—C16—C11	117.35 (19)
C3—C2—C1	120.3 (2)	C15—C16—C20	119.13 (19)
C3—C2—H2	119.8	C11—C16—C20	123.52 (18)
C1—C2—H2	119.8	C12—C17—C18	113.70 (17)
C2—C3—C4	120.6 (2)	C12—C17—C19	110.37 (18)
C2—C3—H3	119.7	C18—C17—C19	110.30 (18)
C4—C3—H3	119.7	C12—C17—H17	107.4
C5—C4—C3	120.6 (2)	C18—C17—H17	107.4
C5—C4—H4	119.7	C19—C17—H17	107.4
C3—C4—H4	119.7	C17—C18—H18A	109.5
C4—C5—C6	120.5 (2)	C17—C18—H18B	109.5
C4—C5—H5	119.8	H18A—C18—H18B	109.5
C6—C5—H5	119.8	C17—C18—H18C	109.5
C7—C6—C5	123.33 (19)	H18A—C18—H18C	109.5
C7—C6—C1	117.73 (18)	H18B—C18—H18C	109.5
C5—C6—C1	118.93 (19)	C17—C19—H19A	109.5
C8—C7—C6	119.5 (2)	C17—C19—H19B	109.5
C8—C7—H7	120.3	H19A—C19—H19B	109.5
C6—C7—H7	120.3	C17—C19—H19C	109.5
C7—C8—C9	119.10 (19)	H19A—C19—H19C	109.5
C7—C8—H8	120.5	H19B—C19—H19C	109.5
C9—C8—H8	120.5	C16—C20—C21	110.49 (18)
N1—C9—C8	123.67 (18)	C16—C20—C22	111.93 (18)
N1—C9—C10	115.18 (19)	C21—C20—C22	110.86 (19)
C8—C9—C10	121.14 (19)	C16—C20—H20	107.8
N2—C10—C9	121.1 (2)	C21—C20—H20	107.8
N2—C10—H10	119.4	C22—C20—H20	107.8
C9—C10—H10	119.4	C20—C21—H21A	109.5
C16—C11—C12	122.09 (18)	C20—C21—H21B	109.5
C16—C11—N2	121.48 (18)	H21A—C21—H21B	109.5
C12—C11—N2	116.34 (18)	C20—C21—H21C	109.5
C13—C12—C11	117.71 (19)	H21A—C21—H21C	109.5
C13—C12—C17	121.52 (18)	H21B—C21—H21C	109.5
C11—C12—C17	120.67 (17)	C20—C22—H22A	109.5
C14—C13—C12	121.2 (2)	C20—C22—H22B	109.5
C14—C13—H13	119.4	H22A—C22—H22B	109.5
C12—C13—H13	119.4	C20—C22—H22C	109.5
C15—C14—C13	120.17 (19)	H22A—C22—H22C	109.5
C15—C14—H14	119.9	H22B—C22—H22C	109.5

C9—N1—C1—C2	179.57 (18)	C10—N2—C11—C12	−118.6 (2)
C9—N1—C1—C6	−0.4 (3)	C16—C11—C12—C13	−0.9 (3)
N1—C1—C2—C3	−179.84 (19)	N2—C11—C12—C13	−177.40 (17)
C6—C1—C2—C3	0.1 (3)	C16—C11—C12—C17	−177.39 (19)
C1—C2—C3—C4	−0.4 (3)	N2—C11—C12—C17	6.1 (3)
C2—C3—C4—C5	0.2 (3)	C11—C12—C13—C14	0.9 (3)
C3—C4—C5—C6	0.3 (3)	C17—C12—C13—C14	177.4 (2)
C4—C5—C6—C7	180.0 (2)	C12—C13—C14—C15	−0.6 (3)
C4—C5—C6—C1	−0.6 (3)	C13—C14—C15—C16	0.3 (3)
N1—C1—C6—C7	−0.2 (3)	C14—C15—C16—C11	−0.2 (3)
C2—C1—C6—C7	179.85 (18)	C14—C15—C16—C20	179.2 (2)
N1—C1—C6—C5	−179.68 (17)	C12—C11—C16—C15	0.6 (3)
C2—C1—C6—C5	0.4 (3)	N2—C11—C16—C15	176.88 (18)
C5—C6—C7—C8	−179.93 (19)	C12—C11—C16—C20	−178.88 (19)
C1—C6—C7—C8	0.6 (3)	N2—C11—C16—C20	−2.6 (3)
C6—C7—C8—C9	−0.5 (3)	C13—C12—C17—C18	33.5 (3)
C1—N1—C9—C8	0.6 (3)	C11—C12—C17—C18	−150.12 (19)
C1—N1—C9—C10	−179.74 (16)	C13—C12—C17—C19	−91.0 (2)
C7—C8—C9—N1	−0.1 (3)	C11—C12—C17—C19	85.3 (2)
C7—C8—C9—C10	−179.82 (18)	C15—C16—C20—C21	66.5 (2)
C11—N2—C10—C9	−177.95 (17)	C11—C16—C20—C21	−114.1 (2)
N1—C9—C10—N2	171.13 (18)	C15—C16—C20—C22	−57.6 (3)
C8—C9—C10—N2	−9.2 (3)	C11—C16—C20—C22	121.8 (2)
C10—N2—C11—C16	64.9 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···N1ⁱ	0.95	2.61	3.464 (3)	151

Symmetry code: (i) x, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₂₂H₂₄N₂
M_r	316.43
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	120
a, b, c (Å)	13.811 (3), 10.971 (2), 11.995 (2)
β (°)	93.88 (3)
V (Å³)	1813.3 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.30 × 0.30 × 0.25

Data collection
Diffractometer	Nonius KappaCCD area-detector
Absorption correction	Multi-scan (XPREP in SHELXTL; Bruker, 1998)
T_min, T_max	0.980, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	29862, 3384, 1994
R_int	0.141
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.116, 1.06
No. of reflections	3384
No. of parameters	221
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.19

Computer programs: COLLECT (Nonius, 1997), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), XP in SHELXTL (Bruker, 1998).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···N1ⁱ	0.9500	2.6100	3.464 (3)	151.00

Symmetry code: (i) x, −y+1/2, z−1/2.

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