(4-Methyl-piperazin-1-yl)(2,3,4-tri-meth-oxy-benzyl-idene)amine.

In the title compound, C15H23N3O3, the piperazine ring is in a slightly distorted chair conformation and is twisted from the mean plane of the benzene ring making a dihedral angle of 14.94 (6)°. The 4-meth-oxy substituent is almost co-planar with the benzene ring [C-C-O-C torsion angle = 5.4 (1)°], while the meth-oxy groups at positions 2 and 3 [C-C-O-C torsion angles of 122.6 (4) and -66.1 (4)°, respectively] are twisted away from the mean plane of the benzene ring in anti-clinical and synclinical conformations, respectively. No classical hydrogen bonds or any weak inter-molecular inter-actions are observed in the crystal structure.

Related literature

For a review of pharmacological and toxicological information for piperazine derivatives, see: Elliott (2011 ▶). For the anti­microbial activity of Schiff base piperazine derivatives, see: Savaliya et al. (2010 ▶) and for their anti­bacterial activity, see: Xu et al. (2012 ▶). For the anti­microbial activity of piperazine derivatives, see: Kharb et al. (2012 ▶). For related structures, see: Kavitha et al. (2013a ▶,b ▶); Guo (2007 ▶); Guo & Qiu (2007 ▶); Xu et al. (2009 ▶); Zhou et al. (2011 ▶). For puckering parameters, see Cremer & Pople (1975 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C15H23N3O3

M = 293.36

Orthorhombic,

a = 7.84207 (14) Å

b = 14.2305 (3) Å

c = 27.6218 (5) Å

V = 3082.49 (10) Å3

Z = 8

Cu Kα radiation

μ = 0.73 mm−1

T = 173 K

0.30 × 0.26 × 0.18 mm

Data collection

Agilent Xcalibur (Eos, Gemini) diffractometer

Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012 ▶) T min = 0.290, T max = 1.000

19693 measured reflections

2978 independent reflections

2643 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.113

S = 1.04

2978 reflections

195 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.17 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012 ▶); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007 ▶); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814006291/hg5389sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814006291/hg5389Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814006291/hg5389Isup3.cml

CCDC reference: 992877

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

C15H23N3O3	Dx = 1.264 Mg m−3
Mr = 293.36	Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, Pbca	Cell parameters from 8346 reflections
a = 7.84207 (14) Å	θ = 4.5–71.5°
b = 14.2305 (3) Å	µ = 0.73 mm−1
c = 27.6218 (5) Å	T = 173 K
V = 3082.49 (10) Å3	Irregular, colourless
Z = 8	0.30 × 0.26 × 0.18 mm
F(000) = 1264

Agilent Xcalibur (Eos, Gemini) diffractometer	2978 independent reflections
Radiation source: Enhance (Cu) X-ray Source	2643 reflections with I > 2σ(I)
Detector resolution: 16.0416 pixels mm-1	Rint = 0.051
ω scans	θmax = 71.3°, θmin = 3.2°
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012)	h = −9→9
Tmin = 0.290, Tmax = 1.000	k = −14→17
19693 measured reflections	l = −33→33

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.040	w = 1/[σ2(Fo2) + (0.0679P)2 + 0.5881P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.113	(Δ/σ)max = 0.001
S = 1.04	Δρmax = 0.23 e Å−3
2978 reflections	Δρmin = −0.17 e Å−3
195 parameters	Extinction correction: SHELXL2012 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraints	Extinction coefficient: 0.00092 (14)
Primary atom site location: structure-invariant direct methods

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

	x	y	z	Uiso*/Ueq
O1	0.29270 (12)	0.40317 (7)	0.53704 (3)	0.0368 (2)
O2	0.27459 (11)	0.21257 (6)	0.51816 (3)	0.0335 (2)
O3	0.44344 (12)	0.08844 (6)	0.57497 (3)	0.0352 (2)
N1	0.44972 (15)	0.77433 (8)	0.70944 (4)	0.0362 (3)
N2	0.54792 (13)	0.60211 (7)	0.66430 (4)	0.0295 (2)
N3	0.54620 (13)	0.50677 (7)	0.65387 (4)	0.0302 (2)
C1	0.44272 (17)	0.76304 (9)	0.65706 (5)	0.0357 (3)
H1A	0.5484	0.7854	0.6429	0.043*
H1B	0.3503	0.8008	0.6442	0.043*
C2	0.41546 (17)	0.66106 (9)	0.64310 (5)	0.0353 (3)
H2A	0.3045	0.6404	0.6544	0.042*
H2B	0.4179	0.6550	0.6081	0.042*
C3	0.56104 (18)	0.61506 (9)	0.71668 (5)	0.0351 (3)
H3A	0.6555	0.5782	0.7291	0.042*
H3B	0.4573	0.5931	0.7321	0.042*
C4	0.58872 (19)	0.71782 (10)	0.72874 (5)	0.0372 (3)
H4A	0.5946	0.7257	0.7636	0.045*
H4B	0.6960	0.7388	0.7150	0.045*
C5	0.46406 (15)	0.47565 (9)	0.61694 (4)	0.0286 (3)
H5	0.4013	0.5165	0.5976	0.034*
C6	0.47012 (14)	0.37502 (9)	0.60550 (4)	0.0279 (3)
C7	0.38193 (14)	0.34008 (9)	0.56495 (4)	0.0276 (3)
C8	0.37692 (14)	0.24401 (9)	0.55517 (4)	0.0278 (3)
C9	0.46380 (15)	0.18119 (9)	0.58557 (4)	0.0285 (3)
C10	0.55834 (16)	0.21556 (9)	0.62441 (4)	0.0318 (3)
H10	0.6207	0.1746	0.6438	0.038*
C11	0.55890 (16)	0.31101 (9)	0.63400 (4)	0.0309 (3)
H11	0.6207	0.3331	0.6604	0.037*
C12	0.4689 (2)	0.87309 (11)	0.72222 (6)	0.0494 (4)
H12A	0.5711	0.8974	0.7078	0.074*
H12B	0.4757	0.8792	0.7568	0.074*
H12C	0.3724	0.9078	0.7105	0.074*
C13	0.3389 (2)	0.40626 (11)	0.48695 (5)	0.0441 (3)
H13A	0.2757	0.3594	0.4695	0.066*
H13B	0.4588	0.3941	0.4837	0.066*
H13C	0.3132	0.4673	0.4741	0.066*
C14	0.36197 (19)	0.16466 (11)	0.47953 (5)	0.0398 (3)
H14A	0.2870	0.1586	0.4522	0.060*
H14B	0.3962	0.1034	0.4903	0.060*
H14C	0.4610	0.2001	0.4703	0.060*
C15	0.51186 (19)	0.02173 (9)	0.60812 (5)	0.0400 (3)
H15A	0.4813	−0.0405	0.5980	0.060*
H15B	0.4666	0.0333	0.6399	0.060*
H15C	0.6338	0.0274	0.6089	0.060*

	U11	U22	U33	U12	U13	U23
O1	0.0377 (5)	0.0364 (5)	0.0363 (5)	0.0096 (4)	−0.0095 (4)	−0.0018 (4)
O2	0.0263 (4)	0.0382 (5)	0.0360 (5)	0.0000 (3)	−0.0049 (3)	−0.0069 (4)
O3	0.0389 (5)	0.0280 (5)	0.0388 (5)	−0.0006 (4)	−0.0020 (4)	0.0006 (4)
N1	0.0396 (6)	0.0337 (6)	0.0353 (6)	−0.0016 (4)	0.0053 (4)	−0.0043 (5)
N2	0.0288 (5)	0.0294 (5)	0.0303 (5)	−0.0002 (4)	−0.0043 (4)	−0.0007 (4)
N3	0.0277 (5)	0.0297 (5)	0.0331 (5)	−0.0011 (4)	−0.0009 (4)	−0.0004 (4)
C1	0.0374 (7)	0.0333 (7)	0.0366 (7)	0.0029 (5)	−0.0056 (5)	−0.0002 (5)
C2	0.0347 (6)	0.0356 (7)	0.0355 (6)	0.0017 (5)	−0.0098 (5)	−0.0020 (5)
C3	0.0395 (7)	0.0360 (7)	0.0298 (6)	−0.0035 (5)	−0.0063 (5)	0.0019 (5)
C4	0.0438 (7)	0.0399 (7)	0.0278 (6)	−0.0075 (6)	−0.0038 (5)	−0.0022 (5)
C5	0.0250 (6)	0.0323 (6)	0.0286 (6)	0.0000 (5)	0.0003 (4)	0.0007 (5)
C6	0.0234 (5)	0.0328 (6)	0.0276 (6)	−0.0008 (4)	0.0031 (4)	−0.0001 (5)
C7	0.0220 (5)	0.0323 (6)	0.0285 (6)	0.0021 (4)	0.0015 (4)	0.0016 (5)
C8	0.0213 (5)	0.0352 (7)	0.0269 (6)	−0.0012 (4)	0.0015 (4)	−0.0022 (5)
C9	0.0260 (6)	0.0293 (6)	0.0300 (6)	−0.0006 (4)	0.0045 (4)	−0.0010 (5)
C10	0.0322 (6)	0.0335 (7)	0.0297 (6)	0.0031 (5)	−0.0026 (5)	0.0040 (5)
C11	0.0297 (6)	0.0363 (7)	0.0267 (6)	−0.0005 (5)	−0.0022 (4)	−0.0017 (5)
C12	0.0702 (11)	0.0380 (8)	0.0400 (8)	−0.0030 (7)	0.0069 (7)	−0.0063 (6)
C13	0.0510 (8)	0.0443 (8)	0.0370 (7)	0.0011 (6)	−0.0104 (6)	0.0083 (6)
C14	0.0409 (7)	0.0442 (8)	0.0343 (7)	0.0017 (6)	−0.0051 (5)	−0.0104 (6)
C15	0.0428 (7)	0.0310 (7)	0.0462 (8)	0.0045 (6)	−0.0006 (6)	0.0029 (6)

O1—C7	1.3747 (15)	C5—H5	0.9300
O1—C13	1.4308 (17)	C5—C6	1.4673 (17)
O2—C8	1.3745 (14)	C6—C7	1.4071 (17)
O2—C14	1.4397 (16)	C6—C11	1.3908 (18)
O3—C9	1.3614 (15)	C7—C8	1.3941 (18)
O3—C15	1.4239 (16)	C8—C9	1.4032 (18)
N1—C1	1.4570 (17)	C9—C10	1.3928 (18)
N1—C4	1.4556 (19)	C10—H10	0.9300
N1—C12	1.4567 (18)	C10—C11	1.3838 (18)
N2—N3	1.3871 (14)	C11—H11	0.9300
N2—C2	1.4579 (16)	C12—H12A	0.9600
N2—C3	1.4623 (16)	C12—H12B	0.9600
N3—C5	1.2852 (16)	C12—H12C	0.9600
C1—H1A	0.9700	C13—H13A	0.9600
C1—H1B	0.9700	C13—H13B	0.9600
C1—C2	1.5167 (18)	C13—H13C	0.9600
C2—H2A	0.9700	C14—H14A	0.9600
C2—H2B	0.9700	C14—H14B	0.9600
C3—H3A	0.9700	C14—H14C	0.9600
C3—H3B	0.9700	C15—H15A	0.9600
C3—C4	1.5154 (18)	C15—H15B	0.9600
C4—H4A	0.9700	C15—H15C	0.9600
C4—H4B	0.9700
C7—O1—C13	115.69 (10)	O1—C7—C6	117.76 (11)
C8—O2—C14	115.31 (10)	O1—C7—C8	121.16 (11)
C9—O3—C15	117.64 (10)	C8—C7—C6	120.97 (11)
C4—N1—C1	109.32 (10)	O2—C8—C7	118.68 (11)
C4—N1—C12	111.54 (12)	O2—C8—C9	121.42 (11)
C12—N1—C1	110.54 (11)	C7—C8—C9	119.68 (11)
N3—N2—C2	118.20 (10)	O3—C9—C8	115.60 (11)
N3—N2—C3	109.23 (10)	O3—C9—C10	124.65 (11)
C2—N2—C3	112.02 (10)	C10—C9—C8	119.72 (11)
C5—N3—N2	120.44 (11)	C9—C10—H10	120.2
N1—C1—H1A	109.4	C11—C10—C9	119.59 (11)
N1—C1—H1B	109.4	C11—C10—H10	120.2
N1—C1—C2	111.30 (11)	C6—C11—H11	118.9
H1A—C1—H1B	108.0	C10—C11—C6	122.20 (11)
C2—C1—H1A	109.4	C10—C11—H11	118.9
C2—C1—H1B	109.4	N1—C12—H12A	109.5
N2—C2—C1	110.37 (10)	N1—C12—H12B	109.5
N2—C2—H2A	109.6	N1—C12—H12C	109.5
N2—C2—H2B	109.6	H12A—C12—H12B	109.5
C1—C2—H2A	109.6	H12A—C12—H12C	109.5
C1—C2—H2B	109.6	H12B—C12—H12C	109.5
H2A—C2—H2B	108.1	O1—C13—H13A	109.5
N2—C3—H3A	109.6	O1—C13—H13B	109.5
N2—C3—H3B	109.6	O1—C13—H13C	109.5
N2—C3—C4	110.43 (10)	H13A—C13—H13B	109.5
H3A—C3—H3B	108.1	H13A—C13—H13C	109.5
C4—C3—H3A	109.6	H13B—C13—H13C	109.5
C4—C3—H3B	109.6	O2—C14—H14A	109.5
N1—C4—C3	110.21 (11)	O2—C14—H14B	109.5
N1—C4—H4A	109.6	O2—C14—H14C	109.5
N1—C4—H4B	109.6	H14A—C14—H14B	109.5
C3—C4—H4A	109.6	H14A—C14—H14C	109.5
C3—C4—H4B	109.6	H14B—C14—H14C	109.5
H4A—C4—H4B	108.1	O3—C15—H15A	109.5
N3—C5—H5	120.3	O3—C15—H15B	109.5
N3—C5—C6	119.41 (11)	O3—C15—H15C	109.5
C6—C5—H5	120.3	H15A—C15—H15B	109.5
C7—C6—C5	120.03 (11)	H15A—C15—H15C	109.5
C11—C6—C5	122.24 (11)	H15B—C15—H15C	109.5
C11—C6—C7	117.73 (11)
O1—C7—C8—O2	−2.82 (16)	C5—C6—C7—C8	−175.85 (10)
O1—C7—C8—C9	−177.37 (10)	C5—C6—C11—C10	177.07 (11)
O2—C8—C9—O3	1.80 (16)	C6—C7—C8—O2	173.26 (10)
O2—C8—C9—C10	−176.27 (11)	C6—C7—C8—C9	−1.30 (16)
O3—C9—C10—C11	−174.78 (11)	C7—C6—C11—C10	−1.90 (18)
N1—C1—C2—N2	−55.98 (15)	C7—C8—C9—O3	176.20 (10)
N2—N3—C5—C6	177.42 (10)	C7—C8—C9—C10	−1.88 (17)
N2—C3—C4—N1	58.01 (14)	C8—C9—C10—C11	3.11 (18)
N3—N2—C2—C1	−177.82 (10)	C9—C10—C11—C6	−1.20 (19)
N3—N2—C3—C4	171.89 (10)	C11—C6—C7—O1	179.34 (10)
N3—C5—C6—C7	−179.49 (11)	C11—C6—C7—C8	3.14 (17)
N3—C5—C6—C11	1.57 (18)	C12—N1—C1—C2	−177.65 (12)
C1—N1—C4—C3	−59.88 (14)	C12—N1—C4—C3	177.56 (11)
C2—N2—N3—C5	19.32 (17)	C13—O1—C7—C6	122.85 (12)
C2—N2—C3—C4	−55.19 (14)	C13—O1—C7—C8	−60.96 (15)
C3—N2—N3—C5	148.93 (11)	C14—O2—C8—C7	119.41 (12)
C3—N2—C2—C1	53.86 (14)	C14—O2—C8—C9	−66.14 (15)
C4—N1—C1—C2	59.20 (14)	C15—O3—C9—C8	−172.57 (11)
C5—C6—C7—O1	0.35 (16)	C15—O3—C9—C10	5.40 (17)