2-[(E)-(Morpholin-4-yl-imino)-meth-yl]-6-(morpholin-4-ylmeth-yl)phenol.

The title compound, C16H23N3O3, contains two morpholine rings, each of which adopts a chair conformation. The mol-ecular conformation is stabilized by an intra-molecular O-H⋯N hydrogen bond, leading to a S(6) ring. In the crystal, mol-ecules are linked into zigzag chains along the c-axis direction by C-H⋯O and C-H⋯π inter-actions.

Related literature

For background to Schiff bases and their applications, see: Dhar & Taploo (1982 ▶); Nelson et al. (2004 ▶); Silva et al. (2011 ▶). For ring puckering parameters, see: Cremer & Pople (1975 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C16H23N3O3

M = 305.37

Monoclinic,

a = 9.0074 (6) Å

b = 15.7781 (14) Å

c = 11.3083 (7) Å

β = 99.052 (5)°

V = 1587.1 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.51 × 0.32 × 0.09 mm

Data collection

STOE IPDS 2 diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.961, T max = 0.990

23637 measured reflections

3289 independent reflections

1955 reflections with I > 2σ(I)

R int = 0.089

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.123

S = 1.03

3289 reflections

199 parameters

H-atom parameters constrained

Δρmax = 0.13 e Å−3

Δρmin = −0.12 e Å−3

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 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681302566X/tk5257sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681302566X/tk5257Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681302566X/tk5257Isup3.cml

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

C16H23N3O3	F(000) = 656
Mr = 305.37	Dx = 1.278 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 17755 reflections
a = 9.0074 (6) Å	θ = 2.2–27.3°
b = 15.7781 (14) Å	µ = 0.09 mm−1
c = 11.3083 (7) Å	T = 296 K
β = 99.052 (5)°	Shapeless, yellow
V = 1587.1 (2) Å3	0.51 × 0.32 × 0.09 mm
Z = 4

STOE IPDS 2 diffractometer	3289 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	1955 reflections with I > 2σ(I)
Plane graphite monochromator	Rint = 0.089
Detector resolution: 6.67 pixels mm-1	θmax = 26.5°, θmin = 2.2°
ω–scans	h = −11→11
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −19→19
Tmin = 0.961, Tmax = 0.990	l = −14→14
23637 measured reflections

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.058	H-atom parameters constrained
wR(F2) = 0.123	W = 1/[Σ2(FO2) + (0.0519P)2] WHERE P = (FO2 + 2FC2)/3
S = 1.03	(Δ/σ)max < 0.001
3289 reflections	Δρmax = 0.13 e Å−3
199 parameters	Δρmin = −0.12 e Å−3

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	0.7886 (2)	0.05694 (15)	0.26574 (16)	0.0912 (9)
O2	0.46117 (17)	0.15800 (11)	0.73906 (12)	0.0586 (5)
O3	0.15802 (19)	0.22570 (11)	1.21636 (13)	0.0659 (6)
N1	0.7555 (2)	0.12192 (11)	0.49469 (14)	0.0497 (6)
N2	0.3995 (2)	0.13953 (12)	0.95782 (15)	0.0500 (6)
N3	0.2980 (2)	0.14585 (12)	1.03797 (14)	0.0514 (6)
C1	0.7095 (3)	0.03684 (16)	0.4572 (2)	0.0669 (9)
C2	0.8012 (4)	0.00352 (19)	0.3670 (2)	0.0838 (11)
C3	0.8362 (4)	0.1393 (2)	0.3018 (2)	0.0859 (13)
C4	0.7453 (3)	0.17607 (16)	0.38952 (19)	0.0614 (8)
C5	0.6625 (3)	0.15608 (18)	0.57868 (19)	0.0667 (9)
C6	0.7055 (3)	0.12328 (14)	0.70585 (18)	0.0523 (8)
C7	0.5991 (2)	0.12627 (13)	0.78287 (18)	0.0467 (7)
C8	0.6357 (2)	0.09994 (13)	0.90283 (18)	0.0452 (7)
C9	0.7809 (3)	0.07110 (14)	0.9425 (2)	0.0562 (8)
C10	0.8869 (3)	0.06887 (16)	0.8678 (2)	0.0629 (9)
C11	0.8489 (3)	0.09507 (15)	0.7501 (2)	0.0600 (9)
C12	0.5296 (3)	0.10624 (14)	0.98800 (18)	0.0501 (8)
C13	0.2093 (3)	0.22298 (16)	1.01350 (19)	0.0584 (9)
C14	0.0910 (3)	0.22850 (19)	1.0939 (2)	0.0691 (10)
C15	0.2348 (3)	0.14835 (18)	1.2391 (2)	0.0707 (10)
C16	0.3593 (3)	0.13650 (15)	1.16513 (18)	0.0566 (8)
H1A	0.60400	0.03710	0.42230	0.0800*
H1B	0.72160	−0.00030	0.52650	0.0800*
H2	0.40790	0.15670	0.79150	0.0880*
H2A	0.90580	−0.00040	0.40360	0.1010*
H2B	0.76680	−0.05290	0.34220	0.1010*
H3A	0.82770	0.17570	0.23190	0.1030*
H3B	0.94120	0.13770	0.33800	0.1030*
H4A	0.78230	0.23230	0.41320	0.0740*
H4B	0.64110	0.18110	0.35220	0.0740*
H5A	0.55830	0.14180	0.55030	0.0800*
H5B	0.67080	0.21740	0.57950	0.0800*
H9	0.80660	0.05290	1.02130	0.0670*
H10	0.98380	0.04990	0.89600	0.0750*
H11	0.92120	0.09370	0.69980	0.0720*
H12	0.55720	0.08570	1.06540	0.0600*
H13A	0.16130	0.22320	0.93050	0.0700*
H13B	0.27480	0.27200	1.02640	0.0700*
H14A	0.03510	0.28090	1.07820	0.0830*
H14B	0.02110	0.18170	1.07680	0.0830*
H15A	0.16360	0.10220	1.22240	0.0850*
H15B	0.27740	0.14560	1.32330	0.0850*
H16A	0.43750	0.17840	1.18800	0.0680*
H16B	0.40340	0.08060	1.17960	0.0680*

	U11	U22	U33	U12	U13	U23
O1	0.1117 (17)	0.1190 (17)	0.0446 (10)	0.0059 (13)	0.0173 (10)	−0.0190 (11)
O2	0.0528 (9)	0.0838 (11)	0.0411 (8)	0.0177 (8)	0.0129 (7)	0.0064 (8)
O3	0.0724 (12)	0.0822 (12)	0.0457 (9)	0.0009 (9)	0.0178 (8)	−0.0106 (8)
N1	0.0550 (11)	0.0584 (12)	0.0378 (9)	0.0049 (9)	0.0141 (8)	0.0022 (8)
N2	0.0553 (12)	0.0586 (11)	0.0379 (9)	−0.0038 (9)	0.0128 (8)	−0.0032 (8)
N3	0.0578 (11)	0.0657 (12)	0.0339 (9)	−0.0087 (10)	0.0168 (8)	−0.0046 (8)
C1	0.0723 (17)	0.0674 (16)	0.0628 (15)	−0.0028 (13)	0.0164 (13)	0.0056 (13)
C2	0.101 (2)	0.085 (2)	0.0652 (17)	0.0133 (17)	0.0121 (16)	−0.0203 (16)
C3	0.086 (2)	0.122 (3)	0.0555 (16)	−0.0115 (19)	0.0288 (15)	0.0107 (17)
C4	0.0664 (15)	0.0706 (16)	0.0480 (13)	−0.0028 (13)	0.0118 (11)	0.0105 (12)
C5	0.0764 (17)	0.0838 (17)	0.0434 (13)	0.0302 (14)	0.0202 (12)	0.0073 (12)
C6	0.0625 (15)	0.0575 (14)	0.0383 (11)	0.0173 (11)	0.0119 (10)	0.0016 (10)
C7	0.0533 (14)	0.0458 (12)	0.0409 (11)	0.0097 (10)	0.0070 (10)	−0.0036 (9)
C8	0.0555 (14)	0.0405 (11)	0.0396 (11)	0.0037 (10)	0.0075 (10)	−0.0008 (9)
C9	0.0722 (16)	0.0564 (14)	0.0390 (12)	0.0141 (12)	0.0053 (11)	0.0014 (10)
C10	0.0619 (16)	0.0742 (16)	0.0509 (14)	0.0248 (13)	0.0036 (12)	0.0025 (12)
C11	0.0608 (16)	0.0727 (16)	0.0494 (13)	0.0222 (12)	0.0177 (11)	0.0032 (12)
C12	0.0702 (17)	0.0460 (12)	0.0352 (11)	−0.0021 (11)	0.0122 (11)	−0.0006 (9)
C13	0.0563 (15)	0.0766 (17)	0.0433 (12)	0.0045 (12)	0.0110 (11)	0.0012 (12)
C14	0.0611 (16)	0.099 (2)	0.0503 (14)	−0.0016 (14)	0.0181 (12)	−0.0086 (14)
C15	0.094 (2)	0.0805 (18)	0.0419 (13)	−0.0078 (16)	0.0245 (13)	−0.0040 (13)
C16	0.0771 (16)	0.0586 (15)	0.0355 (11)	0.0008 (12)	0.0129 (11)	0.0013 (10)

O1—C2	1.412 (3)	C15—C16	1.512 (4)
O1—C3	1.409 (4)	C1—H1A	0.9700
O2—C7	1.359 (2)	C1—H1B	0.9700
O3—C14	1.422 (3)	C2—H2A	0.9700
O3—C15	1.406 (3)	C2—H2B	0.9700
O2—H2	0.8200	C3—H3A	0.9700
N1—C1	1.449 (3)	C3—H3B	0.9700
N1—C5	1.465 (3)	C4—H4A	0.9700
N1—C4	1.456 (3)	C4—H4B	0.9700
N2—N3	1.389 (2)	C5—H5A	0.9700
N2—C12	1.281 (3)	C5—H5B	0.9700
N3—C16	1.464 (3)	C9—H9	0.9300
N3—C13	1.458 (3)	C10—H10	0.9300
C1—C2	1.505 (4)	C11—H11	0.9300
C3—C4	1.499 (4)	C12—H12	0.9300
C5—C6	1.520 (3)	C13—H13A	0.9700
C6—C7	1.394 (3)	C13—H13B	0.9700
C6—C11	1.383 (4)	C14—H14A	0.9700
C7—C8	1.407 (3)	C14—H14B	0.9700
C8—C12	1.463 (3)	C15—H15A	0.9700
C8—C9	1.391 (3)	C15—H15B	0.9700
C9—C10	1.371 (4)	C16—H16A	0.9700
C10—C11	1.384 (3)	C16—H16B	0.9700
C13—C14	1.508 (4)
C2—O1—C3	109.51 (19)	O1—C3—H3B	109.00
C14—O3—C15	109.05 (18)	C4—C3—H3A	109.00
C7—O2—H2	109.00	C4—C3—H3B	109.00
C1—N1—C5	111.37 (19)	H3A—C3—H3B	108.00
C4—N1—C5	110.18 (18)	N1—C4—H4A	110.00
C1—N1—C4	109.06 (17)	N1—C4—H4B	110.00
N3—N2—C12	121.63 (17)	C3—C4—H4A	110.00
N2—N3—C16	116.65 (18)	C3—C4—H4B	110.00
C13—N3—C16	112.40 (17)	H4A—C4—H4B	108.00
N2—N3—C13	109.48 (17)	N1—C5—H5A	109.00
N1—C1—C2	111.1 (2)	N1—C5—H5B	109.00
O1—C2—C1	111.0 (2)	C6—C5—H5A	109.00
O1—C3—C4	112.1 (3)	C6—C5—H5B	109.00
N1—C4—C3	110.0 (2)	H5A—C5—H5B	108.00
N1—C5—C6	113.7 (2)	C8—C9—H9	119.00
C5—C6—C7	118.8 (2)	C10—C9—H9	119.00
C5—C6—C11	122.4 (2)	C9—C10—H10	120.00
C7—C6—C11	118.66 (19)	C11—C10—H10	120.00
O2—C7—C8	121.49 (17)	C6—C11—H11	119.00
C6—C7—C8	120.84 (18)	C10—C11—H11	119.00
O2—C7—C6	117.64 (18)	N2—C12—H12	119.00
C7—C8—C9	118.25 (18)	C8—C12—H12	119.00
C9—C8—C12	119.24 (19)	N3—C13—H13A	110.00
C7—C8—C12	122.43 (18)	N3—C13—H13B	110.00
C8—C9—C10	121.4 (2)	C14—C13—H13A	109.00
C9—C10—C11	119.6 (2)	C14—C13—H13B	110.00
C6—C11—C10	121.3 (2)	H13A—C13—H13B	108.00
N2—C12—C8	121.17 (18)	O3—C14—H14A	109.00
N3—C13—C14	110.6 (2)	O3—C14—H14B	109.00
O3—C14—C13	110.7 (2)	C13—C14—H14A	110.00
O3—C15—C16	113.1 (2)	C13—C14—H14B	110.00
N3—C16—C15	109.4 (2)	H14A—C14—H14B	108.00
N1—C1—H1A	109.00	O3—C15—H15A	109.00
N1—C1—H1B	109.00	O3—C15—H15B	109.00
C2—C1—H1A	109.00	C16—C15—H15A	109.00
C2—C1—H1B	109.00	C16—C15—H15B	109.00
H1A—C1—H1B	108.00	H15A—C15—H15B	108.00
O1—C2—H2A	109.00	N3—C16—H16A	110.00
O1—C2—H2B	109.00	N3—C16—H16B	110.00
C1—C2—H2A	109.00	C15—C16—H16A	110.00
C1—C2—H2B	109.00	C15—C16—H16B	110.00
H2A—C2—H2B	108.00	H16A—C16—H16B	108.00
O1—C3—H3A	109.00
C2—O1—C3—C4	−59.1 (3)	N1—C5—C6—C7	−158.0 (2)
C3—O1—C2—C1	58.2 (3)	C5—C6—C11—C10	177.2 (2)
C14—O3—C15—C16	60.8 (3)	C11—C6—C7—O2	176.9 (2)
C15—O3—C14—C13	−61.0 (3)	C5—C6—C7—O2	0.6 (3)
C1—N1—C4—C3	−55.5 (3)	C7—C6—C11—C10	1.0 (3)
C4—N1—C1—C2	55.8 (3)	C11—C6—C7—C8	−1.0 (3)
C5—N1—C4—C3	−178.0 (2)	C5—C6—C7—C8	−177.3 (2)
C1—N1—C5—C6	78.8 (2)	O2—C7—C8—C9	−177.62 (19)
C4—N1—C5—C6	−160.1 (2)	O2—C7—C8—C12	−1.0 (3)
C5—N1—C1—C2	177.6 (2)	C6—C7—C8—C12	176.8 (2)
C12—N2—N3—C16	17.4 (3)	C6—C7—C8—C9	0.2 (3)
C12—N2—N3—C13	146.5 (2)	C7—C8—C12—N2	−2.9 (3)
N3—N2—C12—C8	−179.97 (19)	C12—C8—C9—C10	−176.1 (2)
C13—N3—C16—C15	50.3 (3)	C7—C8—C9—C10	0.6 (3)
N2—N3—C13—C14	176.21 (18)	C9—C8—C12—N2	173.7 (2)
C16—N3—C13—C14	−52.5 (3)	C8—C9—C10—C11	−0.6 (4)
N2—N3—C16—C15	177.92 (19)	C9—C10—C11—C6	−0.3 (4)
N1—C1—C2—O1	−58.0 (3)	N3—C13—C14—O3	57.5 (3)
O1—C3—C4—N1	58.4 (3)	O3—C15—C16—N3	−55.1 (3)
N1—C5—C6—C11	25.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N2	0.82	1.91	2.636 (2)	146
C13—H13A···O3i	0.97	2.55	3.416 (3)	149
C4—H4A···Cg3i	0.97	2.87	3.646 (3)	138

Table 1

Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C6–C11 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯N2	0.82	1.91	2.636 (2)	146
C13—H13A⋯O3i	0.97	2.55	3.416 (3)	149
C4—H4A⋯Cg3i	0.97	2.87	3.646 (3)	138

Symmetry code: (i) .