Crystal structure of (E)-N-(3,4-di-meth-oxy-benzyl-idene)morpholin-4-amine.

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 mol-ecules into supramolecular chains running along a 21 screw axis parallel to the b-axis direction. Weak C-H⋯π inter-actions are also observed.

Related literature

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

Experimental

Crystal data

C13H18N2O3

M = 250.29

Monoclinic,

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

Data collection

Stoe IPDS 2 diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.962, T max = 0.983

8493 measured reflections

3219 independent reflections

2071 reflections with I > 2σ(I)

R int = 0.229

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 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 ▶), 1353 Friedel pairs

Absolute structure parameter: −0.4 (19)

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; 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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681401678X/rz5130sup1.cif

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

Click here for additional data file.

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

Click here for additional data file.

. DOI: 10.1107/S160053681401678X/rz5130fig1.tif

The mol­ecular structure of the title compound with 30% probability displacement ellipsoids.

Click here for additional data file.

a . DOI: 10.1107/S160053681401678X/rz5130fig2.tif

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.

CCDC reference: 1015028

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

C13H18N2O3	F(000) = 268
Mr = 250.29	Dx = 1.219 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 8791 reflections
a = 9.1644 (6) Å	θ = 3.3–28.7°
b = 6.0277 (6) Å	µ = 0.09 mm−1
c = 13.1327 (9) Å	T = 296 K
β = 109.989 (5)°	Block, colourless
V = 681.75 (10) Å3	0.58 × 0.42 × 0.24 mm
Z = 2

Stoe IPDS 2 diffractometer	3219 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	2071 reflections with I > 2σ(I)
Plane graphite monochromator	Rint = 0.229
Detector resolution: 6.67 pixels mm-1	θmax = 28.4°, θmin = 3.3°
ω scans	h = −12→12
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −8→7
Tmin = 0.962, Tmax = 0.983	l = −17→17
8493 measured reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-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 = 1.00	Δρmax = 0.09 e Å−3
3219 reflections	Δρmin = −0.18 e Å−3
164 parameters	Absolute structure: Flack (1983), 1353 Friedel pairs
1 restraint	Absolute structure parameter: −0.4 (19)

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.

	x	y	z	Uiso*/Ueq
O1	0.87001 (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)
N1	0.5456 (2)	0.1976 (4)	0.89414 (16)	0.0551 (7)
N2	0.3907 (2)	0.1691 (4)	0.83192 (16)	0.0559 (7)
C1	0.6164 (3)	−0.0123 (5)	0.9354 (2)	0.0690 (10)
C2	0.7736 (3)	0.0250 (7)	1.0207 (3)	0.0825 (13)
C3	0.8006 (3)	0.3569 (6)	0.9444 (3)	0.0961 (13)
C4	0.6442 (3)	0.3349 (5)	0.8551 (3)	0.0741 (10)
C5	0.3240 (3)	0.3067 (5)	0.7579 (2)	0.0618 (9)
C6	0.1559 (3)	0.2948 (5)	0.6976 (2)	0.0577 (9)
C7	0.0901 (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)
C11	0.0628 (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)
H1A	0.62780	−0.09990	0.87660	0.0830*
H1B	0.55040	−0.09360	0.96640	0.0830*
H2A	0.76090	0.10140	1.08210	0.0990*
H2B	0.82230	−0.11720	1.04580	0.0990*
H3A	0.86890	0.44530	0.91820	0.1150*
H3B	0.78720	0.43450	1.00540	0.1150*
H4A	0.59760	0.48020	0.83530	0.0890*
H4B	0.65700	0.26800	0.79150	0.0890*
H5	0.38240	0.41810	0.74130	0.0740*
H7	0.15210	0.55610	0.60340	0.0860*
H8	−0.11160	0.55040	0.50700	0.0900*
H11	0.10700	0.02590	0.77200	0.0680*
H12A	−0.49830	0.40600	0.42040	0.1920*
H12B	−0.34400	0.43100	0.39490	0.1920*
H12C	−0.37230	0.57810	0.48490	0.1920*
H13A	−0.21360	−0.29130	0.75850	0.1160*
H13B	−0.08730	−0.12190	0.82530	0.1160*
H13C	−0.05390	−0.27630	0.73970	0.1160*

	U11	U22	U33	U12	U13	U23
O1	0.0392 (9)	0.0779 (15)	0.1082 (16)	0.0027 (11)	0.0100 (9)	0.0184 (13)
O2	0.0436 (10)	0.127 (2)	0.0832 (13)	0.0098 (12)	−0.0007 (9)	0.0218 (14)
O3	0.0453 (9)	0.1042 (16)	0.0703 (11)	−0.0062 (12)	0.0093 (8)	0.0151 (13)
N1	0.0362 (9)	0.0605 (14)	0.0612 (11)	−0.0022 (10)	0.0070 (9)	−0.0039 (11)
N2	0.0393 (9)	0.0702 (15)	0.0539 (11)	0.0014 (11)	0.0105 (8)	−0.0019 (12)
C1	0.0479 (13)	0.070 (2)	0.0838 (18)	−0.0075 (15)	0.0156 (12)	0.0121 (18)
C2	0.0496 (14)	0.093 (3)	0.091 (2)	−0.0002 (17)	0.0060 (14)	0.023 (2)
C3	0.0467 (15)	0.074 (2)	0.138 (3)	−0.0134 (15)	−0.0066 (17)	0.020 (2)
C4	0.0451 (14)	0.0609 (18)	0.102 (2)	−0.0048 (14)	0.0068 (14)	0.0169 (18)
C5	0.0459 (12)	0.0722 (19)	0.0632 (15)	−0.0077 (14)	0.0133 (12)	−0.0020 (16)
C6	0.0446 (12)	0.071 (2)	0.0521 (13)	0.0005 (14)	0.0094 (10)	−0.0019 (14)
C7	0.0562 (14)	0.079 (2)	0.0709 (16)	−0.0042 (16)	0.0100 (13)	0.0092 (17)
C8	0.0605 (15)	0.084 (2)	0.0666 (16)	0.0101 (18)	0.0042 (13)	0.0193 (17)
C9	0.0428 (13)	0.094 (2)	0.0570 (15)	0.0066 (14)	0.0050 (11)	−0.0003 (16)
C10	0.0416 (11)	0.081 (2)	0.0488 (12)	−0.0002 (14)	0.0119 (10)	−0.0001 (15)
C11	0.0436 (11)	0.075 (2)	0.0456 (12)	0.0016 (14)	0.0087 (10)	0.0017 (14)
C12	0.0602 (18)	0.159 (4)	0.130 (3)	0.022 (3)	−0.013 (2)	0.050 (3)
C13	0.0599 (16)	0.092 (2)	0.0796 (18)	−0.0077 (17)	0.0223 (14)	0.0102 (18)

O1—C2	1.408 (4)	C1—H1A	0.9700
O1—C3	1.397 (4)	C1—H1B	0.9700
O2—C9	1.364 (3)	C2—H2A	0.9700
O2—C12	1.435 (6)	C2—H2B	0.9700
O3—C10	1.366 (4)	C3—H3A	0.9700
O3—C13	1.415 (4)	C3—H3B	0.9700
N1—N2	1.385 (3)	C4—H4A	0.9700
N1—C1	1.441 (4)	C4—H4B	0.9700
N1—C4	1.443 (4)	C5—H5	0.9300
N2—C5	1.265 (3)	C7—H7	0.9300
C1—C2	1.509 (4)	C8—H8	0.9300
C3—C4	1.516 (5)	C11—H11	0.9300
C5—C6	1.474 (4)	C12—H12A	0.9600
C6—C7	1.367 (4)	C12—H12B	0.9600
C6—C11	1.391 (4)	C12—H12C	0.9600
C7—C8	1.391 (4)	C13—H13A	0.9600
C8—C9	1.366 (5)	C13—H13B	0.9600
C9—C10	1.409 (4)	C13—H13C	0.9600
C10—C11	1.376 (4)
C2—O1—C3	109.4 (2)	C1—C2—H2B	109.00
C9—O2—C12	116.5 (3)	H2A—C2—H2B	108.00
C10—O3—C13	117.1 (2)	O1—C3—H3A	109.00
N2—N1—C1	110.6 (2)	O1—C3—H3B	109.00
N2—N1—C4	120.1 (2)	C4—C3—H3A	109.00
C1—N1—C4	112.4 (2)	C4—C3—H3B	109.00
N1—N2—C5	120.0 (2)	H3A—C3—H3B	108.00
N1—C1—C2	110.0 (3)	N1—C4—H4A	110.00
O1—C2—C1	111.1 (3)	N1—C4—H4B	110.00
O1—C3—C4	112.4 (3)	C3—C4—H4A	110.00
N1—C4—C3	108.5 (3)	C3—C4—H4B	110.00
N2—C5—C6	121.5 (3)	H4A—C4—H4B	108.00
C5—C6—C7	119.0 (3)	N2—C5—H5	119.00
C5—C6—C11	121.8 (2)	C6—C5—H5	119.00
C7—C6—C11	119.2 (3)	C6—C7—H7	120.00
C6—C7—C8	120.9 (3)	C8—C7—H7	120.00
C7—C8—C9	120.0 (3)	C7—C8—H8	120.00
O2—C9—C8	125.1 (3)	C9—C8—H8	120.00
O2—C9—C10	115.2 (3)	C6—C11—H11	120.00
C8—C9—C10	119.7 (3)	C10—C11—H11	120.00
O3—C10—C9	115.5 (2)	O2—C12—H12A	109.00
O3—C10—C11	125.1 (2)	O2—C12—H12B	109.00
C9—C10—C11	119.3 (3)	O2—C12—H12C	109.00
C6—C11—C10	120.7 (3)	H12A—C12—H12B	109.00
N1—C1—H1A	110.00	H12A—C12—H12C	109.00
N1—C1—H1B	110.00	H12B—C12—H12C	110.00
C2—C1—H1A	110.00	O3—C13—H13A	109.00
C2—C1—H1B	110.00	O3—C13—H13B	109.00
H1A—C1—H1B	108.00	O3—C13—H13C	109.00
O1—C2—H2A	109.00	H13A—C13—H13B	109.00
O1—C2—H2B	109.00	H13A—C13—H13C	109.00
C1—C2—H2A	109.00	H13B—C13—H13C	110.00
C2—O1—C3—C4	−60.7 (3)	N2—C5—C6—C7	180.0 (3)
C3—O1—C2—C1	59.7 (4)	N2—C5—C6—C11	−0.3 (4)
C12—O2—C9—C8	−2.2 (5)	C5—C6—C11—C10	179.7 (3)
C12—O2—C9—C10	178.2 (3)	C11—C6—C7—C8	1.0 (4)
C13—O3—C10—C9	−178.9 (3)	C7—C6—C11—C10	−0.6 (4)
C13—O3—C10—C11	1.5 (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—C3	173.6 (2)	C7—C8—C9—O2	179.4 (3)
C4—N1—C1—C2	54.3 (3)	O2—C9—C10—O3	1.4 (4)
C1—N1—N2—C5	−153.6 (2)	C8—C9—C10—C11	1.3 (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—C6	179.1 (3)
O1—C3—C4—N1	57.1 (3)	C9—C10—C11—C6	−0.6 (4)

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

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) ; (ii) .