erythro-2-Morpholino-1,2-di­phenylethanol

The title compound, C₁₈H₂₁NO₂, consists of two aromatic rings and a morpholine ring attached to an ethanol moiety. The mol­ecule is non-planar. There is an intramolecular O—H...N hydrogen bond.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.054
• wR factor = 0.132
• Data-to-parameter ratio = 13.9

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



GOODF_01  Alert C The least squares goodness of fit parameter lies
          outside the range 0.80 <> 2.00
          Goodness of fit given =      0.728


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check

---

S1. Comment

Photo-initiated free-radical polymerization is of great commercial importance (Davidson, 1999; Pappas, 1978). Techniques such as curing of the coating on various materials, adhesives, printing inks, and photoresists are based on photo-initiated free-radical polymerization. The title compound, (I), was synthesized and used for the polymerization of acrylates and methacrylates (Davidson & Steiner, 1971; Arsu & Aydın, 1999). In this paper we report the structure of (I).

The molecular structure of (I) is shown in Fig. 1. The C5—C12 distance of 1.563 (3) Å is nearly equal to the value of 1.520 (3) Å in (E,E)-4-[3-(dichloro-2-hydroxyphenyl-azo)-2-morpholino-2-butenoyl]morpholine (Ramm et al., 1995). The N1—C1 and N1—C4 bond lengths are 1.472 (3) and 1.475 (3) Å, respectively, and agree with the corresponding distances in 1,3-bis(2-methylphenyl)-2-(4-morpholino)-isothiourea [1.473 (3) and 1.470 (4) Å; Sudha et al.;1996]. The N1—C5 and C12—O2 bond lengths are 1.491 (2) and 1.441 (3) Å, respectively; these are similar to the corresponding bond lengths in the salt of diclofenac with N-(2-hydroxyethyl)morpholine [1.489 (4) and 1.403 (4) Å, respectively; Castellari & Sabatino, 1996]. There is an intramolecular O—H···N hydrogen bond (Table 2). The crystal structure is stabilized by van der Waals interactions.

The molecule (I) contains three ring systems; two phenyl rings and a morpholino ring. For the morpholino ring we calculated, following the method of Cremer & Pople (1975), a phase angle θ₂ =0.030 (2)° and ϕ₂ =320 (5)°, indicating a chair conformation, and a puckering amplitude Q = 0.580 (2) Å.

S2. Experimental

trans-Stilbene oxide (1 g) and 1 molar equivalent of distilled morpholine was refluxed for 12 h with vigorous stirring. The product was extracted with diethyl ether and excess of morpholine was separated by addition of 5 ml of distilled water. The combined organic layers were washed with distilled water several times. The solution was dried over anhydrous magnesium sulfate. The crude product of (I) was recrystallized from ethanol. Mp: 394 K. Analysis calculated for C₁₈H₂₁NO₂: C, 76.30; H, 7.54; N, 5.01. Found, C, 76.43; H, 7.60; N, 4.93. ¹H NMR (100 MHz) in CDCI₃: δ 7.08–7.30 (m,10H), 4.89 (m,1H), 3.89 (m,1H), 3.43 (m, 4H), 3.35 (s, 1H), 2.61 (m, 4H).

S3. Refinement

The hydroxy H atom was located from difference Fourier maps and refined isotropically. The other H atoms were positioned geometrically and refined using a riding model.

Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: WinGX (Farrugia, 1999), PARST (Nardelli, 1995) and PLATON (Spek, 1997).

Figures

Fig. 1. An ORTEPIII drawing (Burnett & Johnson, 1996) of (I), showing the atomic numbering scheme. Displacement ellipsoids of non-H atoms are shown at the 50% probability level.

Erythro-2-morpholino-1,2-diphenyl ethanol

Crystal data

C18H21NO2	F(000) = 608
Mr = 283.36	Dx = 1.192 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3846 reflections
a = 13.4628 (7) Å	θ = 3.1–28.3°
b = 5.8074 (3) Å	µ = 0.08 mm^−1
c = 20.3321 (11) Å	T = 293 K
β = 96.611 (10)°	Slab, colourless
V = 1579.07 (14) Å^3	0.36 × 0.30 × 0.16 mm
Z = 4

Data collection

Siemens SMART CCD area-detector diffractometer	1426 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.082
Graphite monochromator	θmax = 25.0°, θmin = 3.1°
Detector resolution: 8.33 pixels mm^-1	h = −16→14
ω scans	k = −6→6
6883 measured reflections	l = −22→24
2711 independent reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.054	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.132	w = 1/[σ^2(Fo^2)]
S = 0.73	(Δ/σ)max < 0.001
2711 reflections	Δρmax = 0.17 e Å^−3
195 parameters	Δρmin = −0.20 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^* = kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.044 (4)

Special details

Experimental. The data collection covered over a hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different ϕ angle (0,88 and 180°) for the crystal and each exposure of 30 s covered 0.3° in ω. The crystal-to-detector distance was 5 cm and the detector swing angle was −35°. Crystal decay was monitored by repeating fifty initial frames at the end of data collection and analysing the intensity of duplicate reflections, and was found to be negligible.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	−0.14867 (12)	0.0438 (3)	0.11837 (8)	0.0352 (5)
O1	−0.27349 (12)	−0.1238 (4)	0.00323 (8)	0.0705 (6)
O2	−0.15115 (13)	0.3706 (3)	0.22085 (9)	0.0586 (6)
C1	−0.10818 (17)	−0.0346 (4)	0.05795 (11)	0.0484 (7)
H1A	−0.0914	−0.1969	0.0619	0.058*
H1B	−0.0476	0.0501	0.0525	0.058*
C2	−0.18443 (18)	0.0029 (5)	−0.00188 (11)	0.0614 (8)
H2B	−0.2003	0.1656	−0.0059	0.074*
H2C	−0.1560	−0.0443	−0.0415	0.074*
C3	−0.31456 (17)	−0.0566 (5)	0.06180 (12)	0.0645 (8)
H3A	−0.3740	−0.1474	0.0660	0.077*
H3B	−0.3344	0.1039	0.0581	0.077*
C4	−0.24106 (16)	−0.0883 (5)	0.12354 (11)	0.0515 (7)
H4A	−0.2714	−0.0368	0.1620	0.062*
H4B	−0.2249	−0.2503	0.1294	0.062*
C5	−0.07577 (14)	0.0220 (4)	0.17905 (9)	0.0312 (5)
H5A	−0.0655	−0.1419	0.1890	0.037*
C6	0.02507 (14)	0.1294 (4)	0.16976 (10)	0.0332 (5)
C7	0.03364 (18)	0.3404 (4)	0.13865 (12)	0.0505 (7)
H7A	−0.0238	0.4187	0.1215	0.061*
C8	0.1271 (2)	0.4362 (5)	0.13286 (14)	0.0703 (9)
H8A	0.1320	0.5776	0.1120	0.084*
C9	0.2132 (2)	0.3186 (7)	0.15853 (13)	0.0748 (10)
H9A	0.2758	0.3811	0.1545	0.090*
C10	0.20586 (18)	0.1115 (6)	0.18960 (12)	0.0640 (8)
H10A	0.2634	0.0345	0.2073	0.077*
C11	0.11286 (16)	0.0165 (4)	0.19477 (10)	0.0431 (6)
H11A	0.1088	−0.1256	0.2154	0.052*
C12	−0.12205 (15)	0.1375 (4)	0.23795 (10)	0.0388 (6)
H12A	−0.1824	0.0515	0.2453	0.047*
C13	−0.05216 (14)	0.1354 (4)	0.30190 (10)	0.0344 (5)
C14	0.01204 (17)	0.3162 (4)	0.32144 (11)	0.0466 (6)
H14A	0.0124	0.4469	0.2950	0.056*
C15	0.07608 (17)	0.3033 (5)	0.38039 (12)	0.0548 (7)
H15A	0.1186	0.4256	0.3932	0.066*
C16	0.07650 (18)	0.1101 (5)	0.41962 (12)	0.0561 (7)
H16A	0.1194	0.1017	0.4588	0.067*
C17	0.01387 (18)	−0.0694 (5)	0.40104 (11)	0.0552 (7)
H17A	0.0143	−0.2000	0.4275	0.066*
C18	−0.05057 (16)	−0.0569 (4)	0.34249 (11)	0.0451 (6)
H18A	−0.0933	−0.1795	0.3304	0.054*
H2A	−0.174 (2)	0.374 (5)	0.1779 (16)	0.103 (12)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0245 (10)	0.0550 (13)	0.0276 (10)	0.0036 (8)	0.0087 (7)	0.0038 (8)
O1	0.0471 (11)	0.1236 (18)	0.0401 (10)	−0.0111 (11)	0.0014 (8)	−0.0095 (10)
O2	0.0610 (12)	0.0709 (14)	0.0465 (11)	0.0325 (9)	0.0167 (9)	0.0035 (9)
C1	0.0396 (14)	0.0729 (19)	0.0341 (13)	0.0090 (12)	0.0099 (10)	−0.0063 (12)
C2	0.0448 (16)	0.107 (2)	0.0332 (14)	0.0003 (15)	0.0080 (11)	−0.0020 (14)
C3	0.0375 (15)	0.113 (3)	0.0431 (15)	−0.0098 (14)	0.0044 (12)	0.0068 (15)
C4	0.0358 (14)	0.0769 (19)	0.0413 (14)	−0.0091 (12)	0.0029 (11)	0.0083 (13)
C5	0.0276 (11)	0.0361 (13)	0.0311 (11)	0.0004 (9)	0.0078 (9)	0.0053 (9)
C6	0.0301 (12)	0.0404 (14)	0.0317 (11)	0.0012 (10)	0.0146 (9)	−0.0061 (10)
C7	0.0542 (16)	0.0419 (16)	0.0612 (16)	0.0012 (12)	0.0319 (12)	0.0024 (12)
C8	0.090 (2)	0.0566 (19)	0.0711 (19)	−0.0296 (17)	0.0408 (18)	−0.0109 (15)
C9	0.0526 (19)	0.125 (3)	0.0514 (17)	−0.0414 (19)	0.0261 (14)	−0.0298 (18)
C10	0.0310 (15)	0.116 (3)	0.0463 (16)	−0.0056 (15)	0.0083 (12)	−0.0038 (16)
C11	0.0311 (13)	0.0642 (17)	0.0356 (12)	0.0028 (11)	0.0105 (10)	−0.0021 (11)
C12	0.0306 (12)	0.0542 (16)	0.0337 (12)	0.0058 (11)	0.0129 (10)	0.0007 (11)
C13	0.0282 (12)	0.0477 (15)	0.0303 (11)	0.0003 (10)	0.0168 (9)	−0.0021 (10)
C14	0.0488 (15)	0.0493 (16)	0.0445 (14)	−0.0080 (12)	0.0172 (12)	−0.0010 (12)
C15	0.0439 (15)	0.0658 (19)	0.0558 (16)	−0.0110 (13)	0.0104 (12)	−0.0210 (14)
C16	0.0412 (15)	0.086 (2)	0.0402 (14)	0.0059 (14)	0.0023 (11)	−0.0084 (15)
C17	0.0597 (17)	0.0640 (18)	0.0415 (15)	0.0018 (14)	0.0038 (13)	0.0096 (13)
C18	0.0461 (15)	0.0508 (16)	0.0398 (14)	−0.0078 (11)	0.0104 (11)	0.0022 (11)

Geometric parameters (Å, º)

N1—C1	1.472 (3)	C7—C8	1.393 (3)
N1—C4	1.475 (3)	C7—H7A	0.9300
N1—C5	1.491 (2)	C8—C9	1.394 (4)
O1—C2	1.421 (3)	C8—H8A	0.9300
O1—C3	1.424 (3)	C9—C10	1.367 (4)
O2—C12	1.441 (3)	C9—H9A	0.9300
O2—H2A	0.89 (3)	C10—C11	1.383 (3)
C1—C2	1.514 (3)	C10—H10A	0.9300
C1—H1A	0.9700	C11—H11A	0.9300
C1—H1B	0.9700	C12—C13	1.515 (3)
C2—H2B	0.9700	C12—H12A	0.9800
C2—H2C	0.9700	C13—C18	1.387 (3)
C3—C4	1.517 (3)	C13—C14	1.389 (3)
C3—H3A	0.9700	C14—C15	1.396 (3)
C3—H3B	0.9700	C14—H14A	0.9300
C4—H4A	0.9700	C15—C16	1.376 (3)
C4—H4B	0.9700	C15—H15A	0.9300
C5—C6	1.525 (3)	C16—C17	1.366 (3)
C5—C12	1.563 (3)	C16—H16A	0.9300
C5—H5A	0.9800	C17—C18	1.392 (3)
C6—C7	1.390 (3)	C17—H17A	0.9300
C6—C11	1.395 (3)	C18—H18A	0.9300
C1—N1—C4	107.14 (18)	C6—C7—H7A	119.5
C1—N1—C5	113.11 (15)	C8—C7—H7A	119.5
C4—N1—C5	112.15 (16)	C7—C8—C9	119.5 (3)
C2—O1—C3	109.36 (18)	C7—C8—H8A	120.2
C12—O2—H2A	108 (2)	C9—C8—H8A	120.2
N1—C1—C2	110.11 (18)	C10—C9—C8	120.2 (2)
N1—C1—H1A	109.6	C10—C9—H9A	119.9
C2—C1—H1A	109.6	C8—C9—H9A	119.9
N1—C1—H1B	109.6	C9—C10—C11	120.0 (3)
C2—C1—H1B	109.6	C9—C10—H10A	120.0
H1A—C1—H1B	108.2	C11—C10—H10A	120.0
O1—C2—C1	111.5 (2)	C10—C11—C6	121.4 (2)
O1—C2—H2B	109.3	C10—C11—H11A	119.3
C1—C2—H2B	109.3	C6—C11—H11A	119.3
O1—C2—H2C	109.3	O2—C12—C13	109.86 (18)
C1—C2—H2C	109.3	O2—C12—C5	109.85 (16)
H2B—C2—H2C	108.0	C13—C12—C5	113.02 (16)
O1—C3—C4	112.3 (2)	O2—C12—H12A	108.0
O1—C3—H3A	109.1	C13—C12—H12A	108.0
C4—C3—H3A	109.1	C5—C12—H12A	108.0
O1—C3—H3B	109.1	C18—C13—C14	118.2 (2)
C4—C3—H3B	109.1	C18—C13—C12	118.9 (2)
H3A—C3—H3B	107.9	C14—C13—C12	123.0 (2)
N1—C4—C3	110.67 (19)	C13—C14—C15	120.5 (2)
N1—C4—H4A	109.5	C13—C14—H14A	119.7
C3—C4—H4A	109.5	C15—C14—H14A	119.7
N1—C4—H4B	109.5	C16—C15—C14	120.2 (2)
C3—C4—H4B	109.5	C16—C15—H15A	119.9
H4A—C4—H4B	108.1	C14—C15—H15A	119.9
N1—C5—C6	111.92 (16)	C17—C16—C15	120.0 (2)
N1—C5—C12	108.37 (15)	C17—C16—H16A	120.0
C6—C5—C12	111.00 (17)	C15—C16—H16A	120.0
N1—C5—H5A	108.5	C16—C17—C18	120.1 (2)
C6—C5—H5A	108.5	C16—C17—H17A	120.0
C12—C5—H5A	108.5	C18—C17—H17A	120.0
C7—C6—C11	118.0 (2)	C13—C18—C17	121.1 (2)
C7—C6—C5	122.58 (19)	C13—C18—H18A	119.5
C11—C6—C5	119.4 (2)	C17—C18—H18A	119.5
C6—C7—C8	120.9 (2)
C4—N1—C1—C2	58.5 (2)	C8—C9—C10—C11	1.0 (4)
C5—N1—C1—C2	−177.36 (19)	C9—C10—C11—C6	−1.1 (4)
C3—O1—C2—C1	58.3 (3)	C7—C6—C11—C10	0.7 (3)
N1—C1—C2—O1	−61.0 (3)	C5—C6—C11—C10	−177.6 (2)
C2—O1—C3—C4	−56.8 (3)	N1—C5—C12—O2	−54.3 (2)
C1—N1—C4—C3	−56.9 (2)	C6—C5—C12—O2	69.0 (2)
C5—N1—C4—C3	178.39 (19)	N1—C5—C12—C13	−177.35 (17)
O1—C3—C4—N1	57.7 (3)	C6—C5—C12—C13	−54.1 (2)
C1—N1—C5—C6	50.4 (2)	O2—C12—C13—C18	151.10 (19)
C4—N1—C5—C6	171.73 (17)	C5—C12—C13—C18	−85.8 (2)
C1—N1—C5—C12	173.15 (18)	O2—C12—C13—C14	−30.0 (3)
C4—N1—C5—C12	−65.5 (2)	C5—C12—C13—C14	93.0 (2)
N1—C5—C6—C7	43.0 (3)	C18—C13—C14—C15	0.0 (3)
C12—C5—C6—C7	−78.2 (2)	C12—C13—C14—C15	−178.9 (2)
N1—C5—C6—C11	−138.73 (19)	C13—C14—C15—C16	0.3 (4)
C12—C5—C6—C11	100.0 (2)	C14—C15—C16—C17	−0.3 (4)
C11—C6—C7—C8	−0.2 (3)	C15—C16—C17—C18	−0.1 (4)
C5—C6—C7—C8	178.1 (2)	C14—C13—C18—C17	−0.3 (3)
C6—C7—C8—C9	0.1 (4)	C12—C13—C18—C17	178.6 (2)
C7—C8—C9—C10	−0.5 (4)	C16—C17—C18—C13	0.4 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···N1	0.89 (3)	2.31 (3)	2.821 (2)	116 (2)