2-Meth-oxy-4-[(4-methyl-piperazin-1-yl)imino-meth-yl]phenol.

The title compound, C(13)H(19)N(3)O(2), was obtained by the direct solvent-free reaction of 4-hy-droxy-3-meth-oxy-benzaldehyde with 1-amino-4-methyl-piperazine. The piperazine ring adopts a chair conformation. In the crystal, strong inter-molecular O-H⋯N and weak inter-molecular C-H⋯O and C-H⋯N hydrogen bonds help to establish the packing.

Related literature

For the biological properties of piperazine compounds, see: Obniska et al. (2005 ▶); Smid et al. (2005 ▶). For background and related structures, see: Guo (2004 ▶, 2007 ▶).

Experimental

Crystal data

C13H19N3O2

M = 249.31

Orthorhombic,

a = 12.179 (2) Å

b = 18.624 (3) Å

c = 6.0187 (10) Å

V = 1365.1 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.25 × 0.25 × 0.10 mm

Data collection

Siemens SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.642, T max = 0.745

7503 measured reflections

1582 independent reflections

1126 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.077

S = 1.01

1582 reflections

169 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.13 e Å−3

Δρmin = −0.13 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 1999) ▶; software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810051135/im2254sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810051135/im2254Isup2.hkl

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

C13H19N3O2	Dx = 1.213 Mg m−3
Mr = 249.31	Melting point: not measured K
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 1708 reflections
a = 12.179 (2) Å	θ = 2.0–25.1°
b = 18.624 (3) Å	µ = 0.08 mm−1
c = 6.0187 (10) Å	T = 296 K
V = 1365.1 (4) Å3	Club-shaped, colorless
Z = 4	0.25 × 0.25 × 0.10 mm
F(000) = 536

Siemens SMART CCD diffractometer	1582 independent reflections
Radiation source: fine-focus sealed tube	1126 reflections with I > 2σ(I)
graphite	Rint = 0.043
Detector resolution: 9.00 cm pixels mm-1	θmax = 26.7°, θmin = 2.0°
ω scans	h = −15→14
Absorption correction: multi-scan (SADABS; Bruker, 2002)	k = −23→21
Tmin = 0.642, Tmax = 0.745	l = −7→6
7503 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.077	w = 1/[σ2(Fo2) + (0.010P)2 + 0.480P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
1582 reflections	Δρmax = 0.13 e Å−3
169 parameters	Δρmin = −0.13 e Å−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0157 (12)

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
O1	0.38591 (18)	0.68018 (10)	0.1639 (4)	0.0597 (7)
H1	0.440 (3)	0.6712 (18)	0.271 (7)	0.090*
O2	0.39131 (16)	0.56755 (10)	0.4468 (4)	0.0563 (6)
N1	0.02060 (18)	0.33961 (11)	0.1024 (4)	0.0441 (6)
N2	−0.05455 (17)	0.20217 (11)	−0.0440 (5)	0.0459 (6)
N3	0.09346 (17)	0.39555 (11)	0.1421 (5)	0.0460 (6)
C1	0.3972 (3)	0.50737 (15)	0.5919 (6)	0.0621 (9)
H1A	0.3291	0.5025	0.6707	0.093*
H1B	0.4560	0.5143	0.6961	0.093*
H1C	0.4107	0.4647	0.5068	0.093*
C2	0.3147 (2)	0.56473 (14)	0.2784 (5)	0.0406 (7)
C3	0.3161 (2)	0.62428 (13)	0.1367 (5)	0.0433 (7)
C4	0.2429 (2)	0.62631 (14)	−0.0381 (6)	0.0500 (7)
H4	0.2428	0.6656	−0.1336	0.060*
C5	0.1695 (2)	0.57068 (14)	−0.0731 (6)	0.0491 (8)
H5	0.1202	0.5733	−0.1908	0.059*
C6	0.1687 (2)	0.51122 (14)	0.0650 (5)	0.0429 (7)
C7	0.2418 (2)	0.50933 (14)	0.2442 (5)	0.0439 (7)
H7	0.2412	0.4704	0.3408	0.053*
C8	0.0937 (2)	0.45134 (14)	0.0184 (6)	0.0478 (8)
H8A	0.0471	0.4551	−0.1155	0.057*
C9	0.0658 (2)	0.27338 (13)	0.1924 (6)	0.0517 (8)
H9A	0.0887	0.2812	0.3449	0.062*
H9B	0.1299	0.2594	0.1070	0.062*
C10	−0.0186 (2)	0.21406 (15)	0.1845 (6)	0.0518 (8)
H10A	0.0129	0.1702	0.2435	0.062*
H10B	−0.0812	0.2270	0.2759	0.062*
C11	−0.1364 (2)	0.14440 (14)	−0.0515 (7)	0.0655 (10)
H11A	−0.1034	0.1003	−0.0032	0.098*
H11B	−0.1628	0.1390	−0.2009	0.098*
H11C	−0.1967	0.1562	0.0446	0.098*
C12	−0.1020 (2)	0.26857 (13)	−0.1319 (6)	0.0524 (9)
H12A	−0.1667	0.2810	−0.0461	0.063*
H12B	−0.1247	0.2609	−0.2845	0.063*
C13	−0.0210 (2)	0.33023 (15)	−0.1233 (6)	0.0500 (9)
H13A	0.0398	0.3206	−0.2233	0.060*
H13B	−0.0567	0.3741	−0.1718	0.060*

	U11	U22	U33	U12	U13	U23
O1	0.0704 (15)	0.0501 (12)	0.0588 (16)	−0.0206 (11)	−0.0153 (13)	0.0126 (12)
O2	0.0664 (13)	0.0492 (11)	0.0535 (14)	−0.0121 (10)	−0.0184 (14)	0.0125 (12)
N1	0.0432 (13)	0.0371 (12)	0.0519 (17)	−0.0026 (10)	−0.0032 (13)	−0.0023 (12)
N2	0.0443 (12)	0.0383 (12)	0.0550 (17)	−0.0042 (10)	0.0015 (14)	−0.0058 (14)
N3	0.0453 (13)	0.0377 (12)	0.0549 (17)	−0.0026 (11)	0.0025 (13)	−0.0054 (13)
C1	0.075 (2)	0.0572 (18)	0.054 (2)	0.0014 (16)	−0.013 (2)	0.0147 (18)
C2	0.0438 (16)	0.0369 (15)	0.0410 (17)	0.0015 (12)	−0.0031 (14)	0.0023 (14)
C3	0.0462 (16)	0.0365 (15)	0.0473 (19)	−0.0047 (12)	−0.0008 (15)	0.0041 (16)
C4	0.0592 (18)	0.0406 (15)	0.0502 (19)	−0.0013 (14)	−0.0062 (18)	0.0078 (17)
C5	0.0479 (16)	0.0477 (16)	0.052 (2)	0.0020 (14)	−0.0128 (17)	0.0035 (16)
C6	0.0377 (15)	0.0378 (14)	0.053 (2)	0.0014 (12)	−0.0004 (14)	−0.0016 (14)
C7	0.0460 (16)	0.0352 (14)	0.051 (2)	−0.0021 (13)	−0.0013 (16)	0.0065 (14)
C8	0.0420 (16)	0.0428 (15)	0.059 (2)	0.0007 (13)	−0.0032 (15)	−0.0021 (15)
C9	0.0599 (18)	0.0465 (16)	0.049 (2)	−0.0022 (14)	−0.0068 (16)	0.0026 (16)
C10	0.0581 (19)	0.0421 (16)	0.055 (2)	−0.0050 (14)	0.0064 (17)	0.0006 (16)
C11	0.0586 (19)	0.0456 (16)	0.092 (3)	−0.0088 (14)	0.001 (2)	−0.008 (2)
C12	0.0487 (17)	0.0434 (16)	0.065 (2)	0.0024 (14)	−0.0094 (15)	−0.0078 (16)
C13	0.0531 (18)	0.0421 (17)	0.055 (2)	0.0010 (14)	−0.0105 (16)	0.0010 (15)

O1—C3	1.354 (3)	C5—C6	1.385 (4)
O1—H1	0.94 (4)	C5—H5	0.9300
O2—C2	1.378 (3)	C6—C7	1.399 (4)
O2—C1	1.423 (3)	C6—C8	1.468 (4)
N1—N3	1.389 (3)	C7—H7	0.9300
N1—C9	1.456 (3)	C8—H8A	0.9884
N1—C13	1.460 (4)	C9—C10	1.510 (4)
N2—C10	1.460 (4)	C9—H9A	0.9700
N2—C12	1.464 (3)	C9—H9B	0.9700
N2—C11	1.468 (3)	C10—H10A	0.9700
N3—C8	1.278 (3)	C10—H10B	0.9700
C1—H1A	0.9600	C11—H11A	0.9600
C1—H1B	0.9600	C11—H11B	0.9600
C1—H1C	0.9600	C11—H11C	0.9600
C2—C7	1.377 (4)	C12—C13	1.515 (4)
C2—C3	1.399 (4)	C12—H12A	0.9700
C3—C4	1.380 (4)	C12—H12B	0.9700
C4—C5	1.384 (3)	C13—H13A	0.9700
C4—H4	0.9300	C13—H13B	0.9700
C3—O1—H1	113 (2)	N3—C8—C6	120.5 (3)
C2—O2—C1	117.1 (2)	N3—C8—H8A	122.1
N3—N1—C9	109.2 (2)	C6—C8—H8A	117.3
N3—N1—C13	118.1 (2)	N1—C9—C10	110.5 (2)
C9—N1—C13	112.1 (2)	N1—C9—H9A	109.5
C10—N2—C12	109.3 (2)	C10—C9—H9A	109.5
C10—N2—C11	110.1 (3)	N1—C9—H9B	109.5
C12—N2—C11	109.9 (2)	C10—C9—H9B	109.5
C8—N3—N1	120.7 (2)	H9A—C9—H9B	108.1
O2—C1—H1A	109.5	N2—C10—C9	110.2 (3)
O2—C1—H1B	109.5	N2—C10—H10A	109.6
H1A—C1—H1B	109.5	C9—C10—H10A	109.6
O2—C1—H1C	109.5	N2—C10—H10B	109.6
H1A—C1—H1C	109.5	C9—C10—H10B	109.6
H1B—C1—H1C	109.5	H10A—C10—H10B	108.1
C7—C2—O2	125.1 (3)	N2—C11—H11A	109.5
C7—C2—C3	120.7 (3)	N2—C11—H11B	109.5
O2—C2—C3	114.2 (2)	H11A—C11—H11B	109.5
O1—C3—C4	118.5 (3)	N2—C11—H11C	109.5
O1—C3—C2	122.9 (3)	H11A—C11—H11C	109.5
C4—C3—C2	118.6 (2)	H11B—C11—H11C	109.5
C3—C4—C5	120.9 (3)	N2—C12—C13	111.8 (2)
C3—C4—H4	119.6	N2—C12—H12A	109.3
C5—C4—H4	119.6	C13—C12—H12A	109.3
C4—C5—C6	120.8 (3)	N2—C12—H12B	109.3
C4—C5—H5	119.6	C13—C12—H12B	109.3
C6—C5—H5	119.6	H12A—C12—H12B	107.9
C5—C6—C7	118.6 (3)	N1—C13—C12	110.4 (3)
C5—C6—C8	119.9 (3)	N1—C13—H13A	109.6
C7—C6—C8	121.6 (3)	C12—C13—H13A	109.6
C2—C7—C6	120.5 (3)	N1—C13—H13B	109.6
C2—C7—H7	119.8	C12—C13—H13B	109.6
C6—C7—H7	119.8	H13A—C13—H13B	108.1
C9—N1—N3—C8	155.1 (3)	C5—C6—C7—C2	−1.6 (4)
C13—N1—N3—C8	25.5 (4)	C8—C6—C7—C2	177.0 (3)
C1—O2—C2—C7	2.0 (4)	N1—N3—C8—C6	178.2 (2)
C1—O2—C2—C3	−177.6 (3)	C5—C6—C8—N3	178.7 (3)
C7—C2—C3—O1	179.7 (3)	C7—C6—C8—N3	0.1 (4)
O2—C2—C3—O1	−0.7 (4)	N3—N1—C9—C10	171.1 (3)
C7—C2—C3—C4	0.0 (4)	C13—N1—C9—C10	−56.0 (3)
O2—C2—C3—C4	179.6 (3)	C12—N2—C10—C9	−59.3 (3)
O1—C3—C4—C5	−179.8 (3)	C11—N2—C10—C9	179.9 (2)
C2—C3—C4—C5	−0.1 (4)	N1—C9—C10—N2	58.7 (3)
C3—C4—C5—C6	−0.7 (5)	C10—N2—C12—C13	58.0 (3)
C4—C5—C6—C7	1.5 (4)	C11—N2—C12—C13	178.9 (3)
C4—C5—C6—C8	−177.1 (3)	N3—N1—C13—C12	−177.9 (2)
O2—C2—C7—C6	−178.7 (3)	C9—N1—C13—C12	53.7 (3)
C3—C2—C7—C6	0.8 (4)	N2—C12—C13—N1	−54.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N2i	0.94 (4)	1.88 (4)	2.734 (3)	151 (3)
C11—H11A···O2ii	0.96	2.67	3.311 (4)	125.
C5—H5···N1iii	0.93	2.67	3.460 (4)	143.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N2i	0.94 (4)	1.88 (4)	2.734 (3)	151 (3)
C11—H11A⋯O2ii	0.96	2.67	3.311 (4)	125
C5—H5⋯N1iii	0.93	2.67	3.460 (4)	143

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