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

In the title compound, C22H17N3, the dihedral angles between the central benzene ring and the terminal phenyl ring and quinoline ring system (r.m.s. deviation = 0.027 Å) are 44.72 (7) and 9.02 (4)°, respectively, and the bond-angle sum at the amine N atom is 359.9°. In the crystal, the N-H group is not involved in hydrogen bonding and the mol-ecules are linked by weak C-H⋯π inter-actions, generating [010] chains.

Related literature

For applications of quinoline-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 ▶).

Experimental

Crystal data

C22H17N3

M = 323.39

Monoclinic,

a = 17.595 (2) Å

b = 7.3348 (8) Å

c = 12.5712 (18) Å

β = 99.769 (6)°

V = 1598.9 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 100 K

0.29 × 0.21 × 0.15 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.967, T max = 0.984

6866 measured reflections

2964 independent reflections

1557 reflections with I > 2σ(I)

R int = 0.063

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.105

S = 0.97

2964 reflections

234 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.19 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, 2008 ▶); molecular graphics: DIAMOND (Brandenberg & Putz, 2006 ▶); software used to prepare material for publication: DIAMOND.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814016006/hb7248sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814016006/hb7248Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814016006/hb7248Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S1600536814016006/hb7248fig1.tif

The mol­ecular structure of the title compound, with non-H atoms drawn as 40% probability displacement ellipsoids.

CCDC reference: 1012864

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

C22H17N3	F(000) = 680
Mr = 323.39	Dx = 1.343 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 999 reflections
a = 17.595 (2) Å	θ = 2.6–28.6°
b = 7.3348 (8) Å	µ = 0.08 mm−1
c = 12.5712 (18) Å	T = 100 K
β = 99.769 (6)°	Block, yellow
V = 1598.9 (4) Å3	0.29 × 0.21 × 0.15 mm
Z = 4

Bruker SMART APEX CCD diffractometer	2964 independent reflections
Radiation source: fine-focus sealed tube	1557 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.063
ω–scans	θmax = 25.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −19→21
Tmin = 0.967, Tmax = 0.984	k = −8→8
6866 measured reflections	l = −12→15

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105	H atoms treated by a mixture of independent and constrained refinement
S = 0.97	w = 1/[σ2(Fo2) + (0.033P)2] where P = (Fo2 + 2Fc2)/3
2964 reflections	(Δ/σ)max < 0.001
234 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.19 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	0.25415 (13)	0.2764 (3)	0.16305 (19)	0.0148 (6)
C2	0.18560 (13)	0.3785 (3)	0.1579 (2)	0.0186 (6)
H2	0.1771	0.4464	0.2173	0.022*
C3	0.13189 (14)	0.3776 (3)	0.0660 (2)	0.0209 (6)
H3	0.0869	0.4454	0.0635	0.025*
C4	0.14301 (14)	0.2766 (3)	−0.0251 (2)	0.0215 (7)
H4	0.1059	0.2777	−0.0873	0.026*
C5	0.20884 (14)	0.1767 (3)	−0.0211 (2)	0.0208 (6)
H5	0.2164	0.1100	−0.0813	0.025*
C6	0.26537 (14)	0.1730 (3)	0.07237 (19)	0.0155 (6)
C7	0.33399 (13)	0.0704 (3)	0.08109 (19)	0.0173 (6)
H7	0.3429	−0.0027	0.0240	0.021*
C8	0.38676 (14)	0.0787 (3)	0.1728 (2)	0.0174 (6)
H8	0.4318	0.0101	0.1798	0.021*
C9	0.37258 (14)	0.1929 (3)	0.2577 (2)	0.0157 (6)
C10	0.43043 (15)	0.2137 (3)	0.3554 (2)	0.0163 (6)
C11	0.55486 (14)	0.1692 (3)	0.4537 (2)	0.0138 (6)
C12	0.62578 (13)	0.0883 (3)	0.44931 (19)	0.0179 (6)
H12	0.6325	0.0252	0.3874	0.022*
C13	0.68652 (13)	0.0993 (3)	0.5345 (2)	0.0182 (6)
H13	0.7332	0.0432	0.5296	0.022*
C14	0.67803 (14)	0.1942 (3)	0.62763 (19)	0.0159 (6)
C15	0.60659 (14)	0.2723 (3)	0.6334 (2)	0.0182 (6)
H15	0.5996	0.3345	0.6955	0.022*
C16	0.54638 (13)	0.2585 (3)	0.54833 (19)	0.0180 (6)
H16	0.4990	0.3101	0.5543	0.022*
C17	0.81614 (14)	0.1848 (3)	0.7206 (2)	0.0159 (6)
C18	0.85238 (14)	0.2256 (3)	0.6337 (2)	0.0196 (6)
H18	0.8234	0.2653	0.5691	0.023*
C19	0.93117 (15)	0.2075 (3)	0.6429 (2)	0.0246 (7)
H19	0.9548	0.2354	0.5841	0.030*
C20	0.97548 (15)	0.1486 (3)	0.7378 (2)	0.0286 (7)
H20	1.0285	0.1349	0.7431	0.034*
C21	0.93964 (15)	0.1103 (3)	0.8252 (2)	0.0282 (7)
H21	0.9690	0.0731	0.8901	0.034*
C22	0.86074 (14)	0.1270 (3)	0.8167 (2)	0.0211 (7)
H22	0.8372	0.0993	0.8756	0.025*
N1	0.30802 (11)	0.2868 (2)	0.25571 (15)	0.0160 (5)
N2	0.49805 (11)	0.1482 (2)	0.36031 (15)	0.0165 (5)
N3	0.73653 (12)	0.2067 (3)	0.71688 (18)	0.0206 (6)
H3N	0.7212 (13)	0.233 (3)	0.779 (2)	0.034 (8)*
H10	0.4135 (11)	0.284 (3)	0.4156 (16)	0.016 (6)*

	U11	U22	U33	U12	U13	U23
C1	0.0146 (16)	0.0161 (14)	0.0142 (15)	−0.0034 (12)	0.0040 (12)	0.0024 (11)
C2	0.0214 (16)	0.0176 (14)	0.0176 (17)	−0.0046 (12)	0.0052 (13)	0.0003 (12)
C3	0.0174 (16)	0.0222 (15)	0.0226 (18)	0.0018 (12)	0.0021 (13)	0.0023 (13)
C4	0.0190 (17)	0.0225 (15)	0.0204 (17)	−0.0068 (13)	−0.0038 (12)	0.0032 (13)
C5	0.0271 (17)	0.0182 (15)	0.0172 (17)	−0.0056 (13)	0.0041 (13)	−0.0017 (12)
C6	0.0168 (16)	0.0146 (14)	0.0154 (16)	−0.0047 (11)	0.0036 (12)	0.0020 (12)
C7	0.0236 (16)	0.0152 (14)	0.0141 (16)	−0.0031 (12)	0.0063 (13)	−0.0006 (11)
C8	0.0189 (16)	0.0151 (14)	0.0200 (17)	0.0023 (11)	0.0086 (13)	0.0019 (12)
C9	0.0157 (16)	0.0138 (14)	0.0183 (16)	−0.0033 (12)	0.0045 (12)	0.0027 (12)
C10	0.0195 (17)	0.0123 (14)	0.0180 (17)	−0.0002 (12)	0.0056 (13)	−0.0014 (12)
C11	0.0132 (15)	0.0132 (14)	0.0159 (16)	−0.0024 (11)	0.0046 (12)	0.0022 (11)
C12	0.0227 (16)	0.0133 (14)	0.0182 (17)	0.0010 (12)	0.0045 (13)	−0.0013 (11)
C13	0.0141 (16)	0.0167 (14)	0.0236 (18)	0.0053 (11)	0.0027 (13)	0.0018 (12)
C14	0.0180 (16)	0.0155 (14)	0.0134 (16)	−0.0029 (12)	0.0007 (12)	0.0041 (12)
C15	0.0234 (17)	0.0144 (14)	0.0176 (16)	−0.0012 (12)	0.0058 (13)	−0.0013 (11)
C16	0.0160 (16)	0.0205 (15)	0.0190 (16)	−0.0006 (11)	0.0069 (13)	−0.0006 (12)
C17	0.0158 (16)	0.0132 (14)	0.0181 (16)	−0.0023 (11)	0.0007 (12)	−0.0015 (12)
C18	0.0189 (17)	0.0185 (14)	0.0206 (17)	−0.0019 (12)	0.0012 (13)	0.0001 (12)
C19	0.0248 (17)	0.0296 (16)	0.0206 (17)	−0.0071 (13)	0.0070 (13)	−0.0038 (13)
C20	0.0177 (17)	0.0350 (17)	0.033 (2)	−0.0028 (13)	0.0045 (15)	−0.0060 (14)
C21	0.0247 (18)	0.0319 (17)	0.0254 (19)	0.0011 (13)	−0.0031 (14)	−0.0006 (13)
C22	0.0209 (17)	0.0212 (15)	0.0210 (18)	−0.0025 (12)	0.0030 (13)	0.0022 (12)
N1	0.0139 (13)	0.0151 (11)	0.0190 (14)	−0.0002 (10)	0.0026 (10)	0.0026 (9)
N2	0.0152 (13)	0.0157 (12)	0.0179 (14)	−0.0014 (9)	0.0005 (10)	0.0025 (9)
N3	0.0185 (14)	0.0302 (14)	0.0137 (14)	0.0002 (10)	0.0041 (11)	−0.0032 (11)

C1—N1	1.373 (3)	C12—C13	1.381 (3)
C1—C6	1.411 (3)	C12—H12	0.9300
C1—C2	1.412 (3)	C13—C14	1.392 (3)
C2—C3	1.363 (3)	C13—H13	0.9300
C2—H2	0.9300	C14—N3	1.391 (3)
C3—C4	1.405 (3)	C14—C15	1.394 (3)
C3—H3	0.9300	C15—C16	1.375 (3)
C4—C5	1.364 (3)	C15—H15	0.9300
C4—H4	0.9300	C16—H16	0.9300
C5—C6	1.405 (3)	C17—C18	1.387 (3)
C5—H5	0.9300	C17—C22	1.391 (3)
C6—C7	1.411 (3)	C17—N3	1.403 (3)
C7—C8	1.354 (3)	C18—C19	1.378 (3)
C7—H7	0.9300	C18—H18	0.9300
C8—C9	1.412 (3)	C19—C20	1.380 (3)
C8—H8	0.9300	C19—H19	0.9300
C9—N1	1.325 (3)	C20—C21	1.384 (3)
C9—C10	1.464 (3)	C20—H20	0.9300
C10—N2	1.275 (3)	C21—C22	1.380 (3)
C10—H10	1.00 (2)	C21—H21	0.9300
C11—C16	1.388 (3)	C22—H22	0.9300
C11—C12	1.391 (3)	N3—H3N	0.89 (2)
C11—N2	1.415 (3)
N1—C1—C6	123.0 (2)	C12—C13—C14	120.1 (2)
N1—C1—C2	118.1 (2)	C12—C13—H13	119.9
C6—C1—C2	118.9 (2)	C14—C13—H13	119.9
C3—C2—C1	120.0 (2)	N3—C14—C13	122.8 (2)
C3—C2—H2	120.0	N3—C14—C15	118.8 (2)
C1—C2—H2	120.0	C13—C14—C15	118.4 (2)
C2—C3—C4	121.4 (2)	C16—C15—C14	120.8 (2)
C2—C3—H3	119.3	C16—C15—H15	119.6
C4—C3—H3	119.3	C14—C15—H15	119.6
C5—C4—C3	119.2 (2)	C15—C16—C11	121.4 (2)
C5—C4—H4	120.4	C15—C16—H16	119.3
C3—C4—H4	120.4	C11—C16—H16	119.3
C4—C5—C6	121.1 (2)	C18—C17—C22	118.9 (2)
C4—C5—H5	119.4	C18—C17—N3	122.6 (2)
C6—C5—H5	119.4	C22—C17—N3	118.5 (2)
C5—C6—C1	119.3 (2)	C19—C18—C17	120.3 (2)
C5—C6—C7	123.4 (2)	C19—C18—H18	119.9
C1—C6—C7	117.3 (2)	C17—C18—H18	119.9
C8—C7—C6	119.7 (2)	C18—C19—C20	121.0 (3)
C8—C7—H7	120.1	C18—C19—H19	119.5
C6—C7—H7	120.1	C20—C19—H19	119.5
C7—C8—C9	119.2 (2)	C19—C20—C21	118.9 (3)
C7—C8—H8	120.4	C19—C20—H20	120.6
C9—C8—H8	120.4	C21—C20—H20	120.6
N1—C9—C8	123.7 (2)	C22—C21—C20	120.6 (3)
N1—C9—C10	115.7 (2)	C22—C21—H21	119.7
C8—C9—C10	120.6 (2)	C20—C21—H21	119.7
N2—C10—C9	120.8 (2)	C21—C22—C17	120.4 (3)
N2—C10—H10	123.5 (12)	C21—C22—H22	119.8
C9—C10—H10	115.7 (12)	C17—C22—H22	119.8
C16—C11—C12	117.6 (2)	C9—N1—C1	117.0 (2)
C16—C11—N2	126.8 (2)	C10—N2—C11	121.4 (2)
C12—C11—N2	115.6 (2)	C14—N3—C17	128.1 (2)
C13—C12—C11	121.7 (2)	C14—N3—H3N	115.3 (16)
C13—C12—H12	119.1	C17—N3—H3N	116.5 (16)
C11—C12—H12	119.1
N1—C1—C2—C3	177.5 (2)	C13—C14—C15—C16	−1.1 (3)
C6—C1—C2—C3	−0.7 (3)	C14—C15—C16—C11	−1.0 (3)
C1—C2—C3—C4	0.0 (4)	C12—C11—C16—C15	2.2 (3)
C2—C3—C4—C5	0.3 (4)	N2—C11—C16—C15	−179.0 (2)
C3—C4—C5—C6	0.2 (4)	C22—C17—C18—C19	0.5 (3)
C4—C5—C6—C1	−0.9 (3)	N3—C17—C18—C19	177.8 (2)
C4—C5—C6—C7	179.2 (2)	C17—C18—C19—C20	0.1 (4)
N1—C1—C6—C5	−177.0 (2)	C18—C19—C20—C21	−1.0 (4)
C2—C1—C6—C5	1.1 (3)	C19—C20—C21—C22	1.4 (4)
N1—C1—C6—C7	2.9 (3)	C20—C21—C22—C17	−0.8 (4)
C2—C1—C6—C7	−179.0 (2)	C18—C17—C22—C21	−0.1 (3)
C5—C6—C7—C8	177.9 (2)	N3—C17—C22—C21	−177.5 (2)
C1—C6—C7—C8	−2.0 (3)	C8—C9—N1—C1	−2.9 (3)
C6—C7—C8—C9	−1.0 (3)	C10—C9—N1—C1	177.1 (2)
C7—C8—C9—N1	3.7 (3)	C6—C1—N1—C9	−0.5 (3)
C7—C8—C9—C10	−176.3 (2)	C2—C1—N1—C9	−178.6 (2)
N1—C9—C10—N2	−171.1 (2)	C9—C10—N2—C11	179.2 (2)
C8—C9—C10—N2	8.9 (3)	C16—C11—N2—C10	0.0 (3)
C16—C11—C12—C13	−1.5 (3)	C12—C11—N2—C10	178.8 (2)
N2—C11—C12—C13	179.6 (2)	C13—C14—N3—C17	22.2 (4)
C11—C12—C13—C14	−0.5 (3)	C15—C14—N3—C17	−161.0 (2)
C12—C13—C14—N3	178.6 (2)	C18—C17—N3—C14	29.4 (4)
C12—C13—C14—C15	1.8 (3)	C22—C17—N3—C14	−153.2 (2)
N3—C14—C15—C16	−178.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···Cg3i	0.93	2.61	3.430 (2)	148
C12—H12···Cg1i	0.93	2.79	3.536 (2)	138
C13—H13···Cg2i	0.93	2.71	3.508 (3)	145

Table 1

Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the N1/C1/C6–C9, C1–C6 and C11–C16 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯Cg3i	0.93	2.61	3.430 (2)	148
C12—H12⋯Cg1i	0.93	2.79	3.536 (2)	138
C13—H13⋯Cg2i	0.93	2.71	3.508 (3)	145

Symmetry code: (i) .