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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 70| Part 9| September 2014| Page o935
doi:10.1107/S160053681401678X
ADDENDA AND ERRATA

A correction has been published for this article. To view the correction, click here.

Crystal structure of (E)-N-(3,4-di­meth­­oxy­benzyl­­idene)morpholin-4-amine

Sevim Türktekin Çelikesir,a Mehmet Akkurt,a* Aliasghar Jarrahpourb and Orhan Büyükgüngörc

aDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, bDepartment of Chemistry, College of Sciences, Shiraz University, 71454 Shiraz, Iran, and cDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, 55139 Samsun, Turkey
*Correspondence e-mail: akkurt@erciyes.edu.tr

Edited by C. Rizzoli, Universita degli Studi di Parma, Italy (Received 15 July 2014; accepted 21 July 2014; online 1 August 2014)

In the title compound, C13H18N2O3, the benzene ring makes a dihedral angle of 17.19 (11)° with the least-squares plane formed by the four C atoms of the morpholine ring, which adopts a chair conformation. In the crystal, C—H⋯N hydrogen bonds link the mol­ecules into supramolecular chains running along a 21 screw axis parallel to the b-axis direction. Weak C—H⋯π inter­actions are also observed.

CCDC reference: 1015028

1. Related literature

For the structures of related compounds, see: Akkurt et al. (2013[Akkurt, M., Jarrahpour, A., Chermahini, M. M., Aberi, M. & Büyükgüngör, O. (2013). Acta Cryst. E69, o1571.], 2014[Akkurt, M., Jarrahpour, A., Chermahini, M. M., Shiri, P. & Özdemir, N. (2014). Acta Cryst. E70, o289-o290.]). For ring-puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • C13H18N2O3

  • Mr = 250.29

  • Monoclinic, P 21

  • a = 9.1644 (6) Å

  • b = 6.0277 (6) Å

  • c = 13.1327 (9) Å

  • β = 109.989 (5)°

  • V = 681.75 (10) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 296 K

  • 0.58 × 0.42 × 0.24 mm

2.2. Data collection

  • Stoe IPDS 2 diffractometer

  • Absorption correction: integration (X-RED32; Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]) Tmin = 0.962, Tmax = 0.983

  • 8493 measured reflections

  • 3219 independent reflections

  • 2071 reflections with I > 2σ(I)

  • Rint = 0.229

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.046

  • wR(F2) = 0.106

  • S = 1.00

  • 3219 reflections

  • 164 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.09 e Å−3

  • Δρmin = −0.18 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1353 Friedel pairs

  • Absolute structure parameter: −0.4 (19)

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C6–C11 benzene ring.
D—H⋯A D—H H⋯A D⋯A D—H⋯A
C1—H1B⋯N1i 0.97 2.61 3.542 (3) 161
C8—H8⋯Cg1ii 0.93 2.87 3.576 (3) 134
Symmetry codes: (i) [-x+1, y-{\script{1\over 2}}, -z+2]; (ii) [-x, y+{\script{1\over 2}}, -z+1].

Data collection: X-AREA (Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]), PARST (Nardelli, 1983[Nardelli, M. (1983). Comput. Chem. 7, 95-98.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information

CCDC reference: 1015028

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681401678X/rz5130sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681401678X/rz5130Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681401678X/rz5130Isup3.cml

checkCIF report


Comment top

As part of our continuing interest in the design and chemistry of Schiff bases containing a morpholine moiety, the title compound has been synthesized and its crystal structure is reported herein. In the title compound (Fig. 1), the benzene ring (C6–C11) makes a dihedral angle of 17.19 (11)° with the least-squares plane formed by the four C atoms of the morpholine ring (C1–C4/N1/O1), which adopts a chair conformation [the puckering parameters (Cremer & Pople, 1975) are QT = 0.557 (3) Å, θ = 177.2 (3)°, ϕ = 177 (7)°]. The N1–N2–C5–C6, C10–C9–O2–C12 and C9–C10–O3–C13 torsion angles are -173.7 (2), 178.2 (3) and -178.9 (3)°, respectively. The bond lengths and bond angles are normal and comparable with those reported for related compounds (Akkurt et al. 2013, 2014). In the crystal structure, molecules are linked by intermolecular C—H···N hydrogen bonds forming supramolecular chains running along a 21 screw axis parallel to the [010] direction (Table 1, Fig. 2). In addition, weak C—H. . .π interactions also occur (Table 1).

Related literature top

For the structures of related compounds, see: Akkurt et al. (2013, 2014). For ring-puckering parameters, see: Cremer & Pople (1975).

Experimental top

Reaction of 3,4-dimethoxybenzaldehyde (1.0 mmol) with morpholin-4-amine (1.0 mmol) in refluxing ethanol gave the title compound. Recrystallization from ethanol gave colourless crystals in 85 % yield. M.p.: 345-347 K. IR (KBr) cm-1:1604 (C=N). 1H-NMR (250 MHz, CDCl3), δ (ppm): 3.06 (CH2-N, t, 4H, J=5 Hz), 3.79 (CH2-O, t, 4H, J=5 Hz), 3.83 (2OMe, s, 6H), 6.73 (aromatic H, d, 1H, J=7.5 Hz), 6.93 (aromatic H, d, 1H, J=7.5 Hz), 7.49 (aromatic H, s, 1H), 7.81 (HC=N, s, 1H). 13CNMR (62.9 MHz, CDCl3), δ (p.p.m): 52.1 (CH2-N), 55.8 (2OMe), 66.4 (CH2-O), 107.4-137.0 (aromatic carbons), 149.6 (C═N).

Refinement top

All H atoms were located geometrically with C—H = 0.93-0.97 Å, and refined using a riding model with Uiso(H) = 1.2 Ueq(C) or 1.5 Ueq(C) for methyl H atoms. Owing to the poor quality of the crystal, the data obtained were rather poor and the value of Rint remained high (0.229).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012), PARST (Nardelli, 1983) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with 30% probability displacement ellipsoids.
[Figure 2] Fig. 2. Packing diagram of the title compound viewed down the a axis. Hydrogen bonds are indicated by dashed lines. For clarity, H atoms not participating in hydrogen bonding are omitted.
(E)-N-(3,4-Dimethoxybenzylidene)morpholin-4-amine top
Crystal data top
C13H18N2O3F(000) = 268
Mr = 250.29Dx = 1.219 Mg m−3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 8791 reflections
a = 9.1644 (6) Åθ = 3.3–28.7°
b = 6.0277 (6) ŵ = 0.09 mm−1
c = 13.1327 (9) ÅT = 296 K
β = 109.989 (5)°Block, colourless
V = 681.75 (10) Å30.58 × 0.42 × 0.24 mm
Z = 2
Data collection top
Stoe IPDS 2
diffractometer		3219 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus2071 reflections with I > 2σ(I)
Plane graphite monochromatorRint = 0.229
Detector resolution: 6.67 pixels mm-1θmax = 28.4°, θmin = 3.3°
ω scansh = −12→12
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)		k = −8→7
Tmin = 0.962, Tmax = 0.983l = −17→17
8493 measured reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.046 w = 1/[σ2(Fo2) + (0.0511P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.106(Δ/σ)max < 0.001
S = 1.00Δρmax = 0.09 e Å−3
3219 reflectionsΔρmin = −0.18 e Å−3
164 parametersAbsolute structure: Flack (1983), 1353 Friedel pairs
1 restraintAbsolute structure parameter: −0.4 (19)
Crystal data top
C13H18N2O3V = 681.75 (10) Å3
Mr = 250.29Z = 2
Monoclinic, P21Mo Kα radiation
a = 9.1644 (6) ŵ = 0.09 mm−1
b = 6.0277 (6) ÅT = 296 K
c = 13.1327 (9) Å0.58 × 0.42 × 0.24 mm
β = 109.989 (5)°
Data collection top
Stoe IPDS 2
diffractometer		3219 independent reflections
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)		2071 reflections with I > 2σ(I)
Tmin = 0.962, Tmax = 0.983Rint = 0.229
8493 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.046H-atom parameters constrained
wR(F2) = 0.106Δρmax = 0.09 e Å−3
S = 1.00Δρmin = −0.18 e Å−3
3219 reflectionsAbsolute structure: Flack (1983), 1353 Friedel pairs
164 parametersAbsolute structure parameter: −0.4 (19)
1 restraint
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.87001 (19)0.1514 (4)0.97941 (17)0.0790 (8)
O2−0.3171 (2)0.2682 (4)0.53060 (17)0.0904 (9)
O3−0.19462 (19)−0.0304 (4)0.67524 (15)0.0760 (7)
N10.5456 (2)0.1976 (4)0.89414 (16)0.0551 (7)
N20.3907 (2)0.1691 (4)0.83192 (16)0.0559 (7)
C10.6164 (3)−0.0123 (5)0.9354 (2)0.0690 (10)
C20.7736 (3)0.0250 (7)1.0207 (3)0.0825 (13)
C30.8006 (3)0.3569 (6)0.9444 (3)0.0961 (13)
C40.6442 (3)0.3349 (5)0.8551 (3)0.0741 (10)
C50.3240 (3)0.3067 (5)0.7579 (2)0.0618 (9)
C60.1559 (3)0.2948 (5)0.6976 (2)0.0577 (9)
C70.0901 (3)0.4480 (6)0.6185 (2)0.0717 (10)
C8−0.0684 (3)0.4447 (6)0.5604 (2)0.0749 (10)
C9−0.1606 (3)0.2862 (6)0.5817 (2)0.0677 (9)
C10−0.0941 (3)0.1245 (5)0.66164 (19)0.0581 (9)
C110.0628 (3)0.1315 (5)0.71871 (18)0.0564 (9)
C12−0.3889 (4)0.4346 (9)0.4511 (4)0.1281 (18)
C13−0.1323 (3)−0.1930 (6)0.7562 (3)0.0776 (10)
H1A0.62780−0.099900.876600.0830*
H1B0.55040−0.093600.966400.0830*
H2A0.760900.101401.082100.0990*
H2B0.82230−0.117201.045800.0990*
H3A0.868900.445300.918200.1150*
H3B0.787200.434501.005400.1150*
H4A0.597600.480200.835300.0890*
H4B0.657000.268000.791500.0890*
H50.382400.418100.741300.0740*
H70.152100.556100.603400.0860*
H8−0.111600.550400.507000.0900*
H110.107000.025900.772000.0680*
H12A−0.498300.406000.420400.1920*
H12B−0.344000.431000.394900.1920*
H12C−0.372300.578100.484900.1920*
H13A−0.21360−0.291300.758500.1160*
H13B−0.08730−0.121900.825300.1160*
H13C−0.05390−0.276300.739700.1160*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0392 (9)0.0779 (15)0.1082 (16)0.0027 (11)0.0100 (9)0.0184 (13)
O20.0436 (10)0.127 (2)0.0832 (13)0.0098 (12)−0.0007 (9)0.0218 (14)
O30.0453 (9)0.1042 (16)0.0703 (11)−0.0062 (12)0.0093 (8)0.0151 (13)
N10.0362 (9)0.0605 (14)0.0612 (11)−0.0022 (10)0.0070 (9)−0.0039 (11)
N20.0393 (9)0.0702 (15)0.0539 (11)0.0014 (11)0.0105 (8)−0.0019 (12)
C10.0479 (13)0.070 (2)0.0838 (18)−0.0075 (15)0.0156 (12)0.0121 (18)
C20.0496 (14)0.093 (3)0.091 (2)−0.0002 (17)0.0060 (14)0.023 (2)
C30.0467 (15)0.074 (2)0.138 (3)−0.0134 (15)−0.0066 (17)0.020 (2)
C40.0451 (14)0.0609 (18)0.102 (2)−0.0048 (14)0.0068 (14)0.0169 (18)
C50.0459 (12)0.0722 (19)0.0632 (15)−0.0077 (14)0.0133 (12)−0.0020 (16)
C60.0446 (12)0.071 (2)0.0521 (13)0.0005 (14)0.0094 (10)−0.0019 (14)
C70.0562 (14)0.079 (2)0.0709 (16)−0.0042 (16)0.0100 (13)0.0092 (17)
C80.0605 (15)0.084 (2)0.0666 (16)0.0101 (18)0.0042 (13)0.0193 (17)
C90.0428 (13)0.094 (2)0.0570 (15)0.0066 (14)0.0050 (11)−0.0003 (16)
C100.0416 (11)0.081 (2)0.0488 (12)−0.0002 (14)0.0119 (10)−0.0001 (15)
C110.0436 (11)0.075 (2)0.0456 (12)0.0016 (14)0.0087 (10)0.0017 (14)
C120.0602 (18)0.159 (4)0.130 (3)0.022 (3)−0.013 (2)0.050 (3)
C130.0599 (16)0.092 (2)0.0796 (18)−0.0077 (17)0.0223 (14)0.0102 (18)
Geometric parameters (Å, º) top
O1—C21.408 (4)C1—H1A0.9700
O1—C31.397 (4)C1—H1B0.9700
O2—C91.364 (3)C2—H2A0.9700
O2—C121.435 (6)C2—H2B0.9700
O3—C101.366 (4)C3—H3A0.9700
O3—C131.415 (4)C3—H3B0.9700
N1—N21.385 (3)C4—H4A0.9700
N1—C11.441 (4)C4—H4B0.9700
N1—C41.443 (4)C5—H50.9300
N2—C51.265 (3)C7—H70.9300
C1—C21.509 (4)C8—H80.9300
C3—C41.516 (5)C11—H110.9300
C5—C61.474 (4)C12—H12A0.9600
C6—C71.367 (4)C12—H12B0.9600
C6—C111.391 (4)C12—H12C0.9600
C7—C81.391 (4)C13—H13A0.9600
C8—C91.366 (5)C13—H13B0.9600
C9—C101.409 (4)C13—H13C0.9600
C10—C111.376 (4)
C2—O1—C3109.4 (2)C1—C2—H2B109.00
C9—O2—C12116.5 (3)H2A—C2—H2B108.00
C10—O3—C13117.1 (2)O1—C3—H3A109.00
N2—N1—C1110.6 (2)O1—C3—H3B109.00
N2—N1—C4120.1 (2)C4—C3—H3A109.00
C1—N1—C4112.4 (2)C4—C3—H3B109.00
N1—N2—C5120.0 (2)H3A—C3—H3B108.00
N1—C1—C2110.0 (3)N1—C4—H4A110.00
O1—C2—C1111.1 (3)N1—C4—H4B110.00
O1—C3—C4112.4 (3)C3—C4—H4A110.00
N1—C4—C3108.5 (3)C3—C4—H4B110.00
N2—C5—C6121.5 (3)H4A—C4—H4B108.00
C5—C6—C7119.0 (3)N2—C5—H5119.00
C5—C6—C11121.8 (2)C6—C5—H5119.00
C7—C6—C11119.2 (3)C6—C7—H7120.00
C6—C7—C8120.9 (3)C8—C7—H7120.00
C7—C8—C9120.0 (3)C7—C8—H8120.00
O2—C9—C8125.1 (3)C9—C8—H8120.00
O2—C9—C10115.2 (3)C6—C11—H11120.00
C8—C9—C10119.7 (3)C10—C11—H11120.00
O3—C10—C9115.5 (2)O2—C12—H12A109.00
O3—C10—C11125.1 (2)O2—C12—H12B109.00
C9—C10—C11119.3 (3)O2—C12—H12C109.00
C6—C11—C10120.7 (3)H12A—C12—H12B109.00
N1—C1—H1A110.00H12A—C12—H12C109.00
N1—C1—H1B110.00H12B—C12—H12C110.00
C2—C1—H1A110.00O3—C13—H13A109.00
C2—C1—H1B110.00O3—C13—H13B109.00
H1A—C1—H1B108.00O3—C13—H13C109.00
O1—C2—H2A109.00H13A—C13—H13B109.00
O1—C2—H2B109.00H13A—C13—H13C109.00
C1—C2—H2A109.00H13B—C13—H13C110.00
C2—O1—C3—C4−60.7 (3)N2—C5—C6—C7180.0 (3)
C3—O1—C2—C159.7 (4)N2—C5—C6—C11−0.3 (4)
C12—O2—C9—C8−2.2 (5)C5—C6—C11—C10179.7 (3)
C12—O2—C9—C10178.2 (3)C11—C6—C7—C81.0 (4)
C13—O3—C10—C9−178.9 (3)C7—C6—C11—C10−0.6 (4)
C13—O3—C10—C111.5 (4)C5—C6—C7—C8−179.2 (3)
N2—N1—C1—C2−168.4 (2)C6—C7—C8—C9−0.3 (5)
C4—N1—N2—C5−20.1 (4)C7—C8—C9—C10−0.9 (4)
N2—N1—C4—C3173.6 (2)C7—C8—C9—O2179.4 (3)
C4—N1—C1—C254.3 (3)O2—C9—C10—O31.4 (4)
C1—N1—N2—C5−153.6 (2)C8—C9—C10—C111.3 (4)
C1—N1—C4—C3−53.6 (3)O2—C9—C10—C11−179.0 (2)
N1—N2—C5—C6−173.7 (2)C8—C9—C10—O3−178.3 (3)
N1—C1—C2—O1−56.7 (3)O3—C10—C11—C6179.1 (3)
O1—C3—C4—N157.1 (3)C9—C10—C11—C6−0.6 (4)
Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the C6–C11 benzene ring.
D—H···AD—HH···AD···AD—H···A
C1—H1B···N1i0.972.613.542 (3)161
C8—H8···Cg1ii0.932.873.576 (3)134
Symmetry codes: (i) −x+1, y−1/2, −z+2; (ii) −x, y+1/2, −z+1.
Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the C6–C11 benzene ring.
D—H···AD—HH···AD···AD—H···A
C1—H1B···N1i0.972.613.542 (3)161
C8—H8···Cg1ii0.932.873.576 (3)134
Symmetry codes: (i) −x+1, y−1/2, −z+2; (ii) −x, y+1/2, −z+1.
 

Acknowledgements

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDS 2 diffractometer (purchased under grant F.279 of the University Research Fund).

References

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ISSN: 2056-9890
Volume 70| Part 9| September 2014| Page o935
doi:10.1107/S160053681401678X
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