Crystal structure of N (1),N (1)-diethyl-N (4)-[(quinolin-2-yl)methyl-idene]benzene-1,4-di-amine.

The title compound, C20H21N3, is non-planar with a dihedral angle between the planes of the quinoline and phenyl-enedi-amine rings of 9.40 (4)°. In the crystal, mol-ecules are connected by C-H⋯π inter-actions, generating a chain extending along the a-axis direction. Weak C-H⋯π inter-actions also occur.

Related literature

For applications of quinolinyl-containing Schiff bases, see: Das et al. (2013 ▸); Jursic et al. (2002 ▸); Motswainyana et al. (2013 ▸); Song et al. (2011 ▸). The present work is part of an ongoing structural study of Schiff base–metal complexes, see: Faizi & Hussain (2014 ▸); Faizi & Sen (2014 ▸); Faizi et al. (2014 ▸). For related Schiff bases and their applications, see: Gonzalez et al. (2012 ▸); Patra & Goldberg (2003 ▸).

Experimental

Crystal data

C20H21N3

M = 303.40

Orthorhombic,

a = 20.354 (5) Å

b = 7.534 (5) Å

c = 21.801 (5) Å

V = 3343 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.07 mm−1

T = 100 K

0.27 × 0.21 × 0.16 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2008a ▸) T min = 0.981, T max = 0.989

14928 measured reflections

2937 independent reflections

1912 reflections with I > 2σ(I)

R int = 0.146

Refinement

R[F 2 > 2σ(F 2)] = 0.084

wR(F 2) = 0.195

S = 1.09

2937 reflections

212 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.32 e Å−3

Δρmin = −0.23 e Å−3

Data collection: SMART (Bruker, 2003 ▸); cell refinement: SAINT (Bruker, 2003 ▸); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▸); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008b ▸); molecular graphics: DIAMOND (Brandenberg & Putz, 2005 ▸); software used to prepare material for publication: DIAMOND.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989014027108/hg5416sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989014027108/hg5416Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989014027108/hg5416Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989014027108/hg5416fig1.tif

The mol­ecular conformation and atom-numbering scheme for the title compound, with non-H atoms drawn as 40% probability displacement ellipsoids.

Click here for additional data file.

a . DOI: 10.1107/S2056989014027108/hg5416fig2.tif

The mol­ecular packing viewed along the a direction.

CCDC reference: 1038674

Additional supporting information: crystallographic information; 3D view; checkCIF report

C20H21N3	F(000) = 1296
Mr = 303.40	Dx = 1.206 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1765 reflections
a = 20.354 (5) Å	θ = 2.7–27.5°
b = 7.534 (5) Å	µ = 0.07 mm−1
c = 21.801 (5) Å	T = 100 K
V = 3343 (2) Å3	Needle, yellow
Z = 8	0.27 × 0.21 × 0.16 mm

Bruker SMART APEX CCD diffractometer	2937 independent reflections
Radiation source: fine-focus sealed tube	1912 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.146
/w–scans	θmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008a)	h = −24→23
Tmin = 0.981, Tmax = 0.989	k = −8→8
14928 measured reflections	l = −18→25

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)] = 0.084	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.195	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ2(Fo2) + (0.0662P)2 + 3.082P] where P = (Fo2 + 2Fc2)/3
2937 reflections	(Δ/σ)max < 0.001
212 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	0.35623 (17)	−0.0493 (5)	0.07353 (16)	0.0221 (9)
C2	0.38904 (17)	−0.1200 (5)	0.12533 (16)	0.0243 (9)
H2	0.4301	−0.1726	0.1205	0.029*
C3	0.36114 (17)	−0.1119 (5)	0.18233 (16)	0.0241 (9)
H3	0.3830	−0.1600	0.2159	0.029*
C4	0.29920 (19)	−0.0306 (5)	0.19034 (17)	0.0292 (10)
H4	0.2806	−0.0249	0.2292	0.035*
C5	0.26640 (18)	0.0397 (5)	0.14123 (16)	0.0246 (9)
H5	0.2257	0.0930	0.1472	0.029*
C6	0.29346 (17)	0.0326 (4)	0.08169 (16)	0.0195 (8)
C7	0.26231 (17)	0.0998 (5)	0.02881 (16)	0.0233 (9)
H7	0.2216	0.1552	0.0322	0.028*
C8	0.29143 (17)	0.0843 (5)	−0.02734 (16)	0.0237 (9)
H8	0.2705	0.1256	−0.0625	0.028*
C9	0.35419 (17)	0.0040 (5)	−0.03101 (16)	0.0204 (8)
C10	0.38967 (19)	−0.0092 (5)	−0.08980 (17)	0.0232 (9)
C11	0.39650 (17)	0.0327 (5)	−0.19610 (15)	0.0208 (8)
C12	0.45481 (18)	−0.0590 (5)	−0.20748 (16)	0.0229 (8)
H12	0.4741	−0.1235	−0.1759	0.027*
C13	0.48440 (17)	−0.0565 (5)	−0.26392 (15)	0.0225 (9)
H13	0.5233	−0.1190	−0.2696	0.027*
C14	0.45734 (17)	0.0384 (5)	−0.31347 (15)	0.0197 (8)
C15	0.39852 (16)	0.1316 (5)	−0.30210 (16)	0.0208 (8)
H15	0.3792	0.1971	−0.3335	0.025*
C16	0.36925 (17)	0.1269 (5)	−0.24513 (15)	0.0199 (8)
H16	0.3301	0.1883	−0.2391	0.024*
C17	0.46058 (17)	0.1451 (5)	−0.42064 (15)	0.0226 (9)
H17A	0.4951	0.1662	−0.4505	0.027*
H17B	0.4464	0.2595	−0.4051	0.027*
C18	0.40284 (17)	0.0555 (5)	−0.45265 (16)	0.0255 (9)
H18A	0.3874	0.1299	−0.4854	0.038*
H18B	0.3680	0.0367	−0.4237	0.038*
H18C	0.4167	−0.0567	−0.4691	0.038*
C19	0.54187 (16)	−0.0777 (5)	−0.38531 (15)	0.0213 (8)
H19A	0.5381	−0.1130	−0.4280	0.026*
H19B	0.5382	−0.1839	−0.3604	0.026*
C20	0.60919 (18)	0.0044 (6)	−0.37512 (18)	0.0308 (10)
H20A	0.6426	−0.0802	−0.3856	0.046*
H20B	0.6137	0.0375	−0.3328	0.046*
H20C	0.6137	0.1078	−0.4005	0.046*
N1	0.38663 (14)	−0.0612 (4)	0.01724 (13)	0.0227 (8)
N2	0.36253 (14)	0.0420 (4)	−0.13964 (13)	0.0227 (7)
N3	0.48728 (14)	0.0418 (4)	−0.37025 (12)	0.0201 (7)
H10	0.4353 (17)	−0.053 (4)	−0.0845 (14)	0.015 (9)*

	U11	U22	U33	U12	U13	U23
C1	0.021 (2)	0.020 (2)	0.025 (2)	−0.0063 (16)	0.0031 (16)	−0.0065 (16)
C2	0.019 (2)	0.024 (2)	0.030 (2)	−0.0016 (16)	0.0000 (16)	−0.0058 (17)
C3	0.025 (2)	0.028 (2)	0.0193 (19)	−0.0033 (17)	−0.0025 (16)	−0.0011 (16)
C4	0.030 (2)	0.033 (2)	0.025 (2)	−0.0110 (18)	0.0055 (17)	−0.0053 (18)
C5	0.020 (2)	0.027 (2)	0.027 (2)	−0.0042 (16)	0.0055 (16)	−0.0068 (17)
C6	0.0166 (19)	0.0157 (19)	0.0261 (19)	−0.0065 (15)	0.0018 (15)	−0.0037 (15)
C7	0.016 (2)	0.021 (2)	0.033 (2)	0.0013 (15)	0.0014 (16)	−0.0035 (17)
C8	0.023 (2)	0.023 (2)	0.025 (2)	−0.0025 (16)	−0.0044 (16)	−0.0014 (16)
C9	0.022 (2)	0.015 (2)	0.0239 (19)	−0.0012 (15)	−0.0022 (15)	−0.0019 (15)
C10	0.022 (2)	0.022 (2)	0.026 (2)	0.0014 (16)	0.0010 (16)	0.0003 (16)
C11	0.023 (2)	0.023 (2)	0.0170 (18)	−0.0011 (16)	0.0016 (15)	−0.0021 (15)
C12	0.026 (2)	0.021 (2)	0.0212 (19)	0.0028 (16)	−0.0063 (16)	0.0007 (16)
C13	0.019 (2)	0.025 (2)	0.023 (2)	0.0060 (16)	−0.0012 (15)	−0.0025 (16)
C14	0.020 (2)	0.020 (2)	0.0191 (18)	−0.0048 (15)	−0.0011 (15)	−0.0034 (15)
C15	0.0205 (19)	0.022 (2)	0.0196 (19)	0.0039 (16)	−0.0061 (15)	0.0010 (16)
C16	0.0134 (18)	0.024 (2)	0.0224 (19)	−0.0006 (15)	−0.0029 (15)	−0.0050 (16)
C17	0.022 (2)	0.025 (2)	0.0207 (19)	−0.0001 (16)	−0.0018 (15)	0.0002 (16)
C18	0.025 (2)	0.031 (2)	0.0203 (19)	0.0025 (17)	0.0002 (16)	0.0029 (16)
C19	0.019 (2)	0.027 (2)	0.0175 (19)	0.0035 (15)	0.0036 (15)	−0.0015 (16)
C20	0.026 (2)	0.034 (2)	0.032 (2)	0.0057 (18)	0.0025 (17)	0.0039 (19)
N1	0.0247 (18)	0.0214 (19)	0.0221 (17)	−0.0012 (13)	0.0046 (13)	−0.0022 (13)
N2	0.0211 (17)	0.0194 (17)	0.0277 (18)	−0.0012 (13)	−0.0012 (13)	−0.0017 (14)
N3	0.0177 (17)	0.0266 (18)	0.0161 (15)	0.0078 (13)	−0.0002 (12)	0.0001 (13)

C1—N1	1.377 (4)	C12—C13	1.370 (5)
C1—C2	1.416 (5)	C12—H12	0.9300
C1—C6	1.430 (5)	C13—C14	1.408 (5)
C2—C3	1.368 (5)	C13—H13	0.9300
C2—H2	0.9300	C14—N3	1.380 (4)
C3—C4	1.412 (5)	C14—C15	1.410 (5)
C3—H3	0.9300	C15—C16	1.378 (5)
C4—C5	1.368 (5)	C15—H15	0.9300
C4—H4	0.9300	C16—H16	0.9300
C5—C6	1.411 (5)	C17—N3	1.452 (4)
C5—H5	0.9300	C17—C18	1.525 (5)
C6—C7	1.410 (5)	C17—H17A	0.9700
C7—C8	1.365 (5)	C17—H17B	0.9700
C7—H7	0.9300	C18—H18A	0.9600
C8—C9	1.416 (5)	C18—H18B	0.9600
C8—H8	0.9300	C18—H18C	0.9600
C9—N1	1.336 (4)	C19—N3	1.467 (4)
C9—C10	1.474 (5)	C19—C20	1.519 (5)
C10—N2	1.278 (5)	C19—H19A	0.9700
C10—H10	0.99 (3)	C19—H19B	0.9700
C11—C12	1.396 (5)	C20—H20A	0.9600
C11—C16	1.398 (5)	C20—H20B	0.9600
C11—N2	1.413 (4)	C20—H20C	0.9600
N1—C1—C2	118.3 (3)	N3—C14—C13	121.7 (3)
N1—C1—C6	122.7 (3)	N3—C14—C15	121.6 (3)
C2—C1—C6	119.0 (3)	C13—C14—C15	116.8 (3)
C3—C2—C1	120.8 (3)	C16—C15—C14	120.8 (3)
C3—C2—H2	119.6	C16—C15—H15	119.6
C1—C2—H2	119.6	C14—C15—H15	119.6
C2—C3—C4	120.2 (3)	C15—C16—C11	122.1 (3)
C2—C3—H3	119.9	C15—C16—H16	119.0
C4—C3—H3	119.9	C11—C16—H16	119.0
C5—C4—C3	120.4 (3)	N3—C17—C18	113.4 (3)
C5—C4—H4	119.8	N3—C17—H17A	108.9
C3—C4—H4	119.8	C18—C17—H17A	108.9
C4—C5—C6	121.0 (4)	N3—C17—H17B	108.9
C4—C5—H5	119.5	C18—C17—H17B	108.9
C6—C5—H5	119.5	H17A—C17—H17B	107.7
C7—C6—C5	124.3 (3)	C17—C18—H18A	109.5
C7—C6—C1	117.1 (3)	C17—C18—H18B	109.5
C5—C6—C1	118.7 (3)	H18A—C18—H18B	109.5
C8—C7—C6	120.5 (3)	C17—C18—H18C	109.5
C8—C7—H7	119.8	H18A—C18—H18C	109.5
C6—C7—H7	119.8	H18B—C18—H18C	109.5
C7—C8—C9	118.6 (3)	N3—C19—C20	113.6 (3)
C7—C8—H8	120.7	N3—C19—H19A	108.8
C9—C8—H8	120.7	C20—C19—H19A	108.8
N1—C9—C8	124.0 (3)	N3—C19—H19B	108.8
N1—C9—C10	114.7 (3)	C20—C19—H19B	108.8
C8—C9—C10	121.3 (3)	H19A—C19—H19B	107.7
N2—C10—C9	120.5 (3)	C19—C20—H20A	109.5
N2—C10—H10	127.2 (18)	C19—C20—H20B	109.5
C9—C10—H10	112.2 (18)	H20A—C20—H20B	109.5
C12—C11—C16	116.9 (3)	C19—C20—H20C	109.5
C12—C11—N2	126.5 (3)	H20A—C20—H20C	109.5
C16—C11—N2	116.5 (3)	H20B—C20—H20C	109.5
C13—C12—C11	121.8 (3)	C9—N1—C1	117.1 (3)
C13—C12—H12	119.1	C10—N2—C11	120.9 (3)
C11—C12—H12	119.1	C14—N3—C17	121.6 (3)
C12—C13—C14	121.6 (3)	C14—N3—C19	121.6 (3)
C12—C13—H13	119.2	C17—N3—C19	116.3 (3)
C14—C13—H13	119.2
N1—C1—C2—C3	−180.0 (3)	C12—C13—C14—C15	0.4 (5)
C6—C1—C2—C3	0.5 (5)	N3—C14—C15—C16	−180.0 (3)
C1—C2—C3—C4	−0.7 (6)	C13—C14—C15—C16	−0.7 (5)
C2—C3—C4—C5	0.4 (6)	C14—C15—C16—C11	0.9 (5)
C3—C4—C5—C6	0.1 (6)	C12—C11—C16—C15	−0.7 (5)
C4—C5—C6—C7	179.1 (3)	N2—C11—C16—C15	178.5 (3)
C4—C5—C6—C1	−0.2 (5)	C8—C9—N1—C1	0.4 (5)
N1—C1—C6—C7	1.1 (5)	C10—C9—N1—C1	178.8 (3)
C2—C1—C6—C7	−179.5 (3)	C2—C1—N1—C9	179.0 (3)
N1—C1—C6—C5	−179.5 (3)	C6—C1—N1—C9	−1.6 (5)
C2—C1—C6—C5	−0.1 (5)	C9—C10—N2—C11	178.9 (3)
C5—C6—C7—C8	−178.7 (3)	C12—C11—N2—C10	13.1 (6)
C1—C6—C7—C8	0.6 (5)	C16—C11—N2—C10	−166.1 (3)
C6—C7—C8—C9	−1.8 (5)	C13—C14—N3—C17	−177.7 (3)
C7—C8—C9—N1	1.3 (5)	C15—C14—N3—C17	1.5 (5)
C7—C8—C9—C10	−177.1 (3)	C13—C14—N3—C19	11.2 (5)
N1—C9—C10—N2	177.1 (3)	C15—C14—N3—C19	−169.6 (3)
C8—C9—C10—N2	−4.5 (5)	C18—C17—N3—C14	−79.2 (4)
C16—C11—C12—C13	0.4 (5)	C18—C17—N3—C19	92.3 (4)
N2—C11—C12—C13	−178.8 (3)	C20—C19—N3—C14	−94.8 (4)
C11—C12—C13—C14	−0.2 (6)	C20—C19—N3—C17	93.7 (4)
C12—C13—C14—N3	179.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···Cg2i	0.93	2.99	3.705 (5)	135
C7—H7···Cg1i	0.93	2.90	3.612 (5)	135
C13—H13···Cg3ii	0.93	2.84	3.588 (5)	138
C15—H15···Cg2iii	0.93	2.89	3.686 (5)	145
C18—H18A···Cg1iii	0.96	2.95	3.625 (5)	128

Table 1

Hydrogen-bond geometry (, )

Cg1, Cg2 and Cg3 are the centroids of the N1/C1/C6C9, C1C16 and C11C16 rings, respectively.

DHA	DH	HA	D A	DHA
C5H5Cg2i	0.93	2.99	3.705(5)	135
C7H7Cg1i	0.93	2.90	3.612(5)	135
C13H13Cg3ii	0.93	2.84	3.588(5)	138
C15H15Cg2iii	0.93	2.89	3.686(5)	145
C18H18A Cg1iii	0.96	2.95	3.625(5)	128

Symmetry codes: (i) ; (ii) ; (iii) .