2-Cyano-5-({4-[N-methyl-N-(2-hy-droxy-eth-yl)amino] phen-yl}diazen-yl)pyridine.

In the title compound, C(15)H(15)N(5)O, the benzene and pyridine rings make a dihedral angle of 30.86 (7)°. In the crystal, chains of mol-ecules are wrapped around the screw axes into compressed helices, through hydrogen bonding between the hy-droxy and cyano groups. The chains are linked by weak C-H⋯N and C-H⋯O inter-actions. The π conjugated unit of the mol-ecule is almost perpendicular to the helix axis, and the formation of the helix is allowed by a gauche-type torsion angle in the hy-droxy-ethyl tail. In this way, consecutive chromophore units along the chain are placed in a strict anti-parallel arrangement, and this is energetically favoured because of the high dipole moment of the mol-ecule.

Related literature

For general information on non-linear optical compounds, see: Singer et al. (1989 ▶); Dalton (2002 ▶). For structural and theoretical analysis of conjugation in push–pull mol­ecules, see: Gainsford et al. (2008 ▶); Centore et al. (2009 ▶); Capobianco et al. (2012 ▶). For the local packing modes of non-linear optical chromophores, see: Coe et al. (2000 ▶); Thallapally et al. (2002 ▶); Centore et al. (2006 ▶). For theoretical computations on similar compounds, see: Willets et al. (1992 ▶); Castaldo et al. (2002 ▶); Locatelli et al. (2005 ▶). For the CSD see: Allen (2002 ▶). For the synthesis of related compounds, see: Bruno et al. (2002 ▶); Centore et al. (2007 ▶); Centore et al. (2012 ▶).

Experimental

Crystal data

C15H15N5O

M = 281.32

Monoclinic,

a = 17.755 (8) Å

b = 7.240 (4) Å

c = 11.045 (8) Å

β = 101.07 (5)°

V = 1393.4 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.40 × 0.10 × 0.05 mm

Data collection

Bruker–Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.965, T max = 0.996

8528 measured reflections

2403 independent reflections

1336 reflections with I > 2σ(I)

R int = 0.069

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.139

S = 1.02

2403 reflections

191 parameters

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.21 e Å−3

Data collection: COLLECT (Nonius, 1999 ▶); cell refinement: CELLFITW (Centore, 2004 ▶); data reduction: EVALCCD (Duisenberg et al., 2003 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812041396/fj2599sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812041396/fj2599Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812041396/fj2599Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C15H15N5O	Dx = 1.341 Mg m−3
Mr = 281.32	Melting point: 439 K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 17.755 (8) Å	Cell parameters from 76 reflections
b = 7.240 (4) Å	θ = 5.6–23.2°
c = 11.045 (8) Å	µ = 0.09 mm−1
β = 101.07 (5)°	T = 293 K
V = 1393.4 (14) Å3	Plate, red
Z = 4	0.40 × 0.10 × 0.05 mm
F(000) = 592

Bruker–Nonius KappaCCD diffractometer	2403 independent reflections
Radiation source: fine-focus sealed tube	1336 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.069
Detector resolution: 9 pixels mm-1	θmax = 25.0°, θmin = 3.1°
CCD rotation images, thick slices scans	h = −20→21
Absorption correction: multi-scan (SADABS; Bruker, 2001)	k = −7→8
Tmin = 0.965, Tmax = 0.996	l = −13→11
8528 measured reflections

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.139	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0646P)2 + 0.0464P] where P = (Fo2 + 2Fc2)/3
2403 reflections	(Δ/σ)max < 0.001
191 parameters	Δρmax = 0.14 e Å−3
0 restraints	Δρmin = −0.21 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	0.39381 (17)	0.5114 (4)	−0.0089 (3)	0.0658 (9)
H1A	0.4101	0.4652	−0.0821	0.079*
H1B	0.3398	0.5431	−0.0314	0.079*
C2	0.40363 (16)	0.3604 (3)	0.0877 (3)	0.0539 (7)
H2A	0.3763	0.2511	0.0523	0.065*
H2B	0.4576	0.3290	0.1102	0.065*
C3	0.43153 (16)	0.4817 (4)	0.3024 (3)	0.0634 (8)
H3A	0.4355	0.3973	0.3704	0.095*
H3B	0.4154	0.6004	0.3266	0.095*
H3C	0.4806	0.4931	0.2788	0.095*
C4	0.29960 (14)	0.4002 (3)	0.2038 (2)	0.0389 (6)
C5	0.27273 (14)	0.4488 (3)	0.3117 (2)	0.0426 (7)
H5	0.3073	0.4906	0.3803	0.051*
C6	0.19600 (15)	0.4353 (3)	0.3169 (2)	0.0416 (6)
H6	0.1799	0.4664	0.3895	0.050*
C7	0.14206 (14)	0.3759 (3)	0.2154 (2)	0.0356 (6)
C8	0.16750 (14)	0.3312 (3)	0.1079 (2)	0.0412 (6)
H8	0.1322	0.2941	0.0388	0.049*
C9	0.24378 (14)	0.3407 (3)	0.1019 (2)	0.0423 (7)
H9	0.2593	0.3072	0.0292	0.051*
C10	−0.03818 (14)	0.3687 (3)	0.3055 (2)	0.0377 (6)
C11	−0.09206 (15)	0.4028 (3)	0.2005 (2)	0.0445 (7)
H11	−0.0770	0.4255	0.1258	0.053*
C12	−0.16836 (15)	0.4026 (3)	0.2081 (2)	0.0479 (7)
H12	−0.2061	0.4250	0.1387	0.058*
C13	−0.18771 (15)	0.3687 (3)	0.3206 (3)	0.0420 (6)
C14	−0.06318 (15)	0.3353 (3)	0.4146 (2)	0.0484 (7)
H14	−0.0264	0.3124	0.4852	0.058*
C15	−0.26695 (18)	0.3730 (3)	0.3352 (3)	0.0519 (7)
N1	0.37562 (12)	0.4124 (3)	0.1987 (2)	0.0459 (6)
N2	0.06251 (12)	0.3612 (2)	0.21080 (19)	0.0417 (5)
N3	0.04319 (12)	0.3723 (3)	0.3147 (2)	0.0455 (6)
N4	−0.13639 (13)	0.3339 (3)	0.4246 (2)	0.0493 (6)
N5	−0.32935 (16)	0.3783 (3)	0.3473 (3)	0.0743 (8)
O1	0.43618 (12)	0.6724 (3)	0.0323 (2)	0.0771 (7)
H1O	0.4068	0.7588	0.0816	0.093*

	U11	U22	U33	U12	U13	U23
C1	0.0473 (19)	0.093 (2)	0.063 (2)	0.0003 (17)	0.0247 (16)	0.0034 (17)
C2	0.0400 (17)	0.0608 (17)	0.067 (2)	0.0028 (13)	0.0272 (15)	−0.0057 (14)
C3	0.0399 (18)	0.086 (2)	0.064 (2)	−0.0063 (15)	0.0079 (16)	0.0043 (16)
C4	0.0361 (17)	0.0363 (14)	0.0476 (17)	0.0008 (11)	0.0161 (13)	0.0059 (11)
C5	0.0417 (17)	0.0504 (15)	0.0365 (16)	−0.0018 (11)	0.0096 (13)	0.0015 (11)
C6	0.0458 (18)	0.0425 (14)	0.0411 (16)	0.0033 (11)	0.0202 (14)	0.0034 (11)
C7	0.0308 (15)	0.0362 (13)	0.0420 (16)	−0.0004 (10)	0.0128 (13)	0.0053 (11)
C8	0.0390 (17)	0.0465 (15)	0.0391 (16)	−0.0018 (11)	0.0102 (13)	−0.0007 (11)
C9	0.0440 (18)	0.0458 (15)	0.0411 (17)	−0.0047 (12)	0.0186 (13)	−0.0054 (11)
C10	0.0328 (16)	0.0368 (14)	0.0464 (17)	−0.0024 (10)	0.0152 (13)	−0.0026 (11)
C11	0.0447 (18)	0.0501 (15)	0.0432 (17)	−0.0018 (12)	0.0195 (14)	−0.0005 (11)
C12	0.0415 (19)	0.0572 (17)	0.0463 (18)	0.0016 (12)	0.0113 (14)	0.0006 (12)
C13	0.0404 (17)	0.0366 (14)	0.0537 (18)	−0.0061 (11)	0.0207 (15)	−0.0089 (12)
C14	0.0409 (19)	0.0608 (17)	0.0449 (18)	−0.0036 (13)	0.0117 (14)	0.0022 (12)
C15	0.049 (2)	0.0473 (16)	0.064 (2)	−0.0056 (13)	0.0236 (16)	−0.0076 (13)
N1	0.0332 (14)	0.0546 (13)	0.0525 (15)	0.0002 (10)	0.0153 (11)	−0.0010 (10)
N2	0.0466 (16)	0.0383 (12)	0.0435 (14)	0.0014 (9)	0.0174 (11)	0.0022 (9)
N3	0.0462 (16)	0.0468 (12)	0.0469 (14)	−0.0011 (10)	0.0180 (11)	0.0027 (10)
N4	0.0442 (16)	0.0613 (14)	0.0461 (15)	−0.0063 (11)	0.0183 (12)	−0.0022 (10)
N5	0.0514 (19)	0.0733 (17)	0.108 (2)	−0.0089 (13)	0.0397 (16)	−0.0089 (15)
O1	0.0668 (16)	0.0722 (14)	0.1043 (18)	−0.0004 (11)	0.0466 (13)	0.0101 (12)

C1—O1	1.414 (3)	C7—N2	1.408 (3)
C1—C2	1.514 (4)	C8—C9	1.370 (3)
C1—H1A	0.9700	C8—H8	0.9300
C1—H1B	0.9700	C9—H9	0.9300
C2—N1	1.458 (3)	C10—C11	1.376 (4)
C2—H2A	0.9700	C10—C14	1.383 (3)
C2—H2B	0.9700	C10—N3	1.429 (3)
C3—N1	1.454 (3)	C11—C12	1.373 (3)
C3—H3A	0.9600	C11—H11	0.9300
C3—H3B	0.9600	C12—C13	1.373 (3)
C3—H3C	0.9600	C12—H12	0.9300
C4—N1	1.365 (3)	C13—N4	1.346 (3)
C4—C5	1.410 (3)	C13—C15	1.447 (4)
C4—C9	1.416 (3)	C14—N4	1.325 (3)
C5—C6	1.378 (3)	C14—H14	0.9300
C5—H5	0.9300	C15—N5	1.142 (3)
C6—C7	1.395 (3)	N2—N3	1.262 (3)
C6—H6	0.9300	O1—H1O	1.0341
C7—C8	1.387 (3)
O1—C1—C2	112.8 (2)	C9—C8—C7	121.1 (2)
O1—C1—H1A	109.0	C9—C8—H8	119.4
C2—C1—H1A	109.0	C7—C8—H8	119.4
O1—C1—H1B	109.0	C8—C9—C4	121.6 (2)
C2—C1—H1B	109.0	C8—C9—H9	119.2
H1A—C1—H1B	107.8	C4—C9—H9	119.2
N1—C2—C1	113.2 (2)	C11—C10—C14	118.5 (2)
N1—C2—H2A	108.9	C11—C10—N3	125.9 (2)
C1—C2—H2A	108.9	C14—C10—N3	115.5 (2)
N1—C2—H2B	108.9	C12—C11—C10	118.9 (3)
C1—C2—H2B	108.9	C12—C11—H11	120.6
H2A—C2—H2B	107.8	C10—C11—H11	120.6
N1—C3—H3A	109.5	C13—C12—C11	118.5 (3)
N1—C3—H3B	109.5	C13—C12—H12	120.8
H3A—C3—H3B	109.5	C11—C12—H12	120.8
N1—C3—H3C	109.5	N4—C13—C12	124.0 (3)
H3A—C3—H3C	109.5	N4—C13—C15	115.0 (2)
H3B—C3—H3C	109.5	C12—C13—C15	121.0 (3)
N1—C4—C5	121.1 (2)	N4—C14—C10	123.9 (3)
N1—C4—C9	122.2 (2)	N4—C14—H14	118.1
C5—C4—C9	116.6 (2)	C10—C14—H14	118.1
C6—C5—C4	121.0 (2)	N5—C15—C13	179.3 (3)
C6—C5—H5	119.5	C4—N1—C3	121.4 (2)
C4—C5—H5	119.5	C4—N1—C2	121.2 (2)
C5—C6—C7	121.3 (2)	C3—N1—C2	117.4 (2)
C5—C6—H6	119.3	N3—N2—C7	114.1 (2)
C7—C6—H6	119.3	N2—N3—C10	112.4 (2)
C8—C7—C6	118.3 (2)	C14—N4—C13	116.2 (2)
C8—C7—N2	116.1 (2)	C1—O1—H1O	112.1
C6—C7—N2	125.6 (2)
O1—C1—C2—N1	62.7 (3)	C11—C10—C14—N4	0.0 (3)
N1—C4—C5—C6	−179.6 (2)	N3—C10—C14—N4	177.4 (2)
C9—C4—C5—C6	1.1 (3)	C5—C4—N1—C3	−2.1 (3)
C4—C5—C6—C7	−1.0 (3)	C9—C4—N1—C3	177.2 (2)
C5—C6—C7—C8	−0.3 (3)	C5—C4—N1—C2	179.4 (2)
C5—C6—C7—N2	−178.6 (2)	C9—C4—N1—C2	−1.4 (3)
C6—C7—C8—C9	1.5 (3)	C1—C2—N1—C4	82.0 (3)
N2—C7—C8—C9	180.0 (2)	C1—C2—N1—C3	−96.6 (3)
C7—C8—C9—C4	−1.4 (3)	C8—C7—N2—N3	168.65 (18)
N1—C4—C9—C8	−179.2 (2)	C6—C7—N2—N3	−13.0 (3)
C5—C4—C9—C8	0.1 (3)	C7—N2—N3—C10	176.23 (17)
C14—C10—C11—C12	0.1 (3)	C11—C10—N3—N2	−18.0 (3)
N3—C10—C11—C12	−176.9 (2)	C14—C10—N3—N2	164.91 (19)
C10—C11—C12—C13	0.1 (3)	C10—C14—N4—C13	−0.4 (3)
C11—C12—C13—N4	−0.6 (4)	C12—C13—N4—C14	0.7 (3)
C11—C12—C13—C15	177.8 (2)	C15—C13—N4—C14	−177.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···N5i	1.03	1.92	2.925 (4)	165
C6—H6···N4ii	0.93	2.74	3.637 (4)	162
C2—H2B···O1iii	0.97	2.68	3.369 (4)	129

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯N5i	1.03	1.92	2.925 (4)	165
C6—H6⋯N4ii	0.93	2.74	3.637 (4)	162
C2—H2B⋯O1iii	0.97	2.68	3.369 (4)	129

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