Crystal structure of 2-[4-(methyl­sulfan­yl)quinazolin-2-yl]-1-phenyl­ethanol

In the mol­ecule of the title compound, C₁₇H₁₆N₂OS, the almost planar methyl­sulfanylquinazoline group [the methyl C atom deviates by 0.032 (2) Å from the plane through the ring system] forms an inter­planar angle of 76.26 (4)° with the plane of the phenyl group. An intra­molecular O—H...N hydrogen bond is present between the quinazoline and hy­droxy groups. In the crystal, mol­ecules are stacked along the b-axis direction.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• R factor = 0.032
• wR factor = 0.094
• Data-to-parameter ratio = 15.3

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S1. Comment

In C₁₇H₁₆N₂OS (Fig. 1), the methylsulfanylquinazoline group is planar and is oriented at an angle of 76.26 (4)° with the phenyl group. The hydroxyl group forms an intramolecular hydrogen bond to one of the quinazoline ring nitrogen atoms (Table 1) whereas the second N atom is not involved in hydrogen bonding. In the crystal structure, molecules are stacked along the b-axis direction (Fig. 2).

Related literature

For the synthesis of 4-(methylsulfanyl)quinazoline derivatives, see: Smith et al. (2005a,b); Leonard & Curtin (1946); Meerwein et al. (1956). For the X-ray structures of related compounds, see: Alshammari et al. (2014a,b).

S2. Experimental

Synthesis and crystallization: 2-(2-hydroxy-2-phenylethyl)-4-(methylsulfanyl)quinazoline was obtained in 83% yield from lithiation of 2-methyl-4-(methylsulfanyl)quinazoline with n-butyllithium at 78°C in anhydrous THF under nitrogen followed by reaction with benzaldehyde (Smith et al., 2005b). Crystallization from a mixture of ethyl acetate and diethyl ether (1:3 by volume) gave the title compound as colorless crystals. The NMR and low and high resolution mass spectra for the title compound were consistent with those reported (Smith et al., 2005b).

S3. Refinement

H atoms were positioned geometrically and refined using a riding model with U_iso(H) constrained to be 1.2 times U_eq(C) except for the methyl group where it was 1.5 times with free rotation about the C—C bond. For the OH group, U_iso(H) 1.5 times U_eq(O) was used with free rotation about the C—O bond.

Computing details

Data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SHELXL2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al. 2006), ORTEP-3 for Windows (Farrugia, 2012) and CHEMDRAW Ultra (Cambridge Soft, 2001); software used to prepare material for publication: publCIF, (Westrip, 2010).

Figures

	Fig. 1. A molecule of C17H16N2OS with atom labels and 50% probability displacement ellipsoids for nonhydrogen atoms.
	Fig. 2. Crystal structure packing viewed down the b axis.

2-[4-(Methylsulfanyl)quinazolin-2-yl]-1-phenylethanol

Crystal data

C17H16N2OS	F(000) = 624
Mr = 296.38	Dx = 1.328 Mg m^−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54184 Å
a = 15.6142 (3) Å	Cell parameters from 5816 reflections
b = 5.6142 (1) Å	θ = 3.5–73.7°
c = 17.2355 (3) Å	µ = 1.93 mm^−1
β = 101.138 (2)°	T = 293 K
V = 1482.43 (5) Å^3	Block, colourless
Z = 4	0.32 × 0.19 × 0.14 mm

Data collection

Agilent SuperNova (Dual, Cu at 0, Atlas) diffractometer	2688 reflections with I > 2σ(I)
ω scans	Rint = 0.014
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	θmax = 74.0°, θmin = 3.5°
Tmin = 0.867, Tmax = 1.000	h = −19→19
9606 measured reflections	k = −6→6
2938 independent reflections	l = −11→21

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.032	H-atom parameters constrained
wR(F^2) = 0.094	w = 1/[σ^2(Fo^2) + (0.0507P)^2 + 0.2343P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.001
2938 reflections	Δρmax = 0.16 e Å^−3
192 parameters	Δρmin = −0.28 e Å^−3

Special details

Experimental. Absorption correction: CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) Empirical absorption correction in SCALE3 ABSPACK.

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

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

	x	y	z	Uiso*/Ueq
C1	0.67633 (8)	0.0261 (2)	0.10297 (7)	0.0458 (3)
C2	0.68632 (8)	−0.1600 (2)	0.04845 (7)	0.0450 (3)
C3	0.62090 (9)	−0.3225 (3)	0.01440 (8)	0.0553 (3)
H3	0.5652	−0.3110	0.0258	0.066*
C4	0.63923 (10)	−0.4967 (3)	−0.03523 (9)	0.0601 (4)
H4	0.5961	−0.6048	−0.0569	0.072*
C5	0.72249 (10)	−0.5136 (3)	−0.05366 (8)	0.0569 (3)
H5	0.7342	−0.6336	−0.0873	0.068*
C6	0.78660 (9)	−0.3561 (3)	−0.02273 (8)	0.0523 (3)
H6	0.8413	−0.3669	−0.0363	0.063*
C7	0.76994 (8)	−0.1775 (2)	0.02961 (7)	0.0444 (3)
C8	0.81859 (8)	0.1354 (2)	0.11131 (7)	0.0445 (3)
C9	0.59215 (12)	0.3019 (3)	0.19721 (11)	0.0734 (5)
H9A	0.6392	0.2626	0.2400	0.110*
H9B	0.5401	0.3312	0.2176	0.110*
H9C	0.6070	0.4421	0.1708	0.110*
C10	0.88942 (8)	0.3057 (2)	0.14745 (8)	0.0479 (3)
H10A	0.8870	0.3261	0.2029	0.058*
H10B	0.8775	0.4595	0.1220	0.058*
C11	0.98167 (8)	0.2298 (2)	0.14133 (7)	0.0429 (3)
H11	0.9941	0.0764	0.1683	0.051*
C12	1.04767 (8)	0.4094 (2)	0.18105 (7)	0.0414 (3)
C13	1.06970 (9)	0.6065 (2)	0.14024 (8)	0.0483 (3)
H13	1.0441	0.6280	0.0873	0.058*
C14	1.12977 (9)	0.7713 (2)	0.17802 (9)	0.0538 (3)
H14	1.1449	0.9011	0.1499	0.065*
C15	1.16716 (9)	0.7448 (2)	0.25659 (9)	0.0544 (3)
H15	1.2075	0.8556	0.2815	0.065*
C16	1.14426 (9)	0.5519 (3)	0.29825 (8)	0.0541 (3)
H16	1.1681	0.5350	0.3517	0.065*
C17	1.08585 (8)	0.3841 (2)	0.26030 (8)	0.0477 (3)
H17	1.0720	0.2526	0.2883	0.057*
N1	0.83603 (7)	−0.0253 (2)	0.06177 (6)	0.0475 (3)
N2	0.74020 (7)	0.1686 (2)	0.13399 (6)	0.0475 (3)
O1	0.99198 (7)	0.2036 (2)	0.06187 (6)	0.0606 (3)
H1	0.9563	0.1070	0.0393	0.091*
S1	0.57374 (2)	0.05921 (7)	0.12865 (2)	0.06185 (14)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0408 (6)	0.0551 (7)	0.0426 (6)	0.0077 (5)	0.0110 (5)	0.0052 (5)
C2	0.0415 (6)	0.0531 (7)	0.0399 (6)	0.0044 (5)	0.0071 (5)	0.0040 (5)
C3	0.0463 (7)	0.0683 (9)	0.0517 (7)	−0.0049 (6)	0.0101 (6)	−0.0006 (6)
C4	0.0609 (8)	0.0649 (8)	0.0529 (8)	−0.0122 (7)	0.0070 (6)	−0.0060 (6)
C5	0.0654 (9)	0.0565 (8)	0.0487 (7)	0.0011 (7)	0.0105 (6)	−0.0077 (6)
C6	0.0504 (7)	0.0597 (8)	0.0474 (7)	0.0065 (6)	0.0107 (5)	−0.0063 (6)
C7	0.0414 (6)	0.0508 (7)	0.0405 (6)	0.0059 (5)	0.0065 (5)	0.0007 (5)
C8	0.0398 (6)	0.0514 (7)	0.0418 (6)	0.0076 (5)	0.0072 (5)	−0.0004 (5)
C9	0.0777 (11)	0.0691 (10)	0.0845 (11)	0.0061 (8)	0.0435 (9)	−0.0105 (8)
C10	0.0431 (6)	0.0510 (7)	0.0492 (7)	0.0052 (5)	0.0078 (5)	−0.0062 (5)
C11	0.0433 (6)	0.0459 (6)	0.0410 (6)	0.0028 (5)	0.0123 (5)	0.0009 (5)
C12	0.0376 (6)	0.0434 (6)	0.0451 (6)	0.0061 (5)	0.0129 (5)	−0.0006 (5)
C13	0.0508 (7)	0.0475 (7)	0.0482 (6)	0.0057 (5)	0.0139 (5)	0.0037 (5)
C14	0.0538 (7)	0.0434 (6)	0.0691 (8)	0.0010 (6)	0.0244 (6)	0.0017 (6)
C15	0.0451 (7)	0.0510 (7)	0.0677 (8)	−0.0014 (6)	0.0123 (6)	−0.0110 (6)
C16	0.0479 (7)	0.0604 (8)	0.0517 (7)	0.0045 (6)	0.0038 (6)	−0.0037 (6)
C17	0.0468 (6)	0.0489 (7)	0.0477 (6)	0.0037 (5)	0.0098 (5)	0.0039 (5)
N1	0.0390 (5)	0.0554 (6)	0.0482 (5)	0.0046 (4)	0.0084 (4)	−0.0067 (5)
N2	0.0429 (5)	0.0546 (6)	0.0462 (5)	0.0072 (5)	0.0116 (4)	−0.0021 (5)
O1	0.0655 (6)	0.0740 (7)	0.0477 (5)	−0.0177 (5)	0.0247 (4)	−0.0148 (5)
S1	0.0459 (2)	0.0755 (3)	0.0698 (2)	0.00317 (16)	0.02499 (17)	−0.00692 (17)

Geometric parameters (Å, º)

C1—N2	1.3092 (17)	C9—H9C	0.9600
C1—C2	1.4340 (18)	C10—C11	1.5252 (16)
C1—S1	1.7521 (13)	C10—H10A	0.9700
C2—C7	1.4083 (17)	C10—H10B	0.9700
C2—C3	1.4100 (19)	C11—O1	1.4173 (14)
C3—C4	1.365 (2)	C11—C12	1.5082 (17)
C3—H3	0.9300	C11—H11	0.9800
C4—C5	1.400 (2)	C12—C17	1.3880 (17)
C4—H4	0.9300	C12—C13	1.3894 (18)
C5—C6	1.365 (2)	C13—C14	1.3873 (19)
C5—H5	0.9300	C13—H13	0.9300
C6—C7	1.4065 (18)	C14—C15	1.375 (2)
C6—H6	0.9300	C14—H14	0.9300
C7—N1	1.3713 (17)	C15—C16	1.384 (2)
C8—N1	1.3067 (16)	C15—H15	0.9300
C8—N2	1.3678 (16)	C16—C17	1.3843 (19)
C8—C10	1.5032 (18)	C16—H16	0.9300
C9—S1	1.7902 (17)	C17—H17	0.9300
C9—H9A	0.9600	O1—H1	0.8200
C9—H9B	0.9600
N2—C1—C2	122.82 (11)	C11—C10—H10A	108.5
N2—C1—S1	119.58 (10)	C8—C10—H10B	108.5
C2—C1—S1	117.60 (10)	C11—C10—H10B	108.5
C7—C2—C3	119.24 (12)	H10A—C10—H10B	107.5
C7—C2—C1	115.14 (11)	O1—C11—C12	108.24 (10)
C3—C2—C1	125.62 (12)	O1—C11—C10	112.40 (10)
C4—C3—C2	120.08 (13)	C12—C11—C10	110.70 (10)
C4—C3—H3	120.0	O1—C11—H11	108.5
C2—C3—H3	120.0	C12—C11—H11	108.5
C3—C4—C5	120.48 (13)	C10—C11—H11	108.5
C3—C4—H4	119.8	C17—C12—C13	118.57 (12)
C5—C4—H4	119.8	C17—C12—C11	120.28 (11)
C6—C5—C4	120.70 (13)	C13—C12—C11	121.12 (11)
C6—C5—H5	119.7	C14—C13—C12	120.31 (12)
C4—C5—H5	119.7	C14—C13—H13	119.8
C5—C6—C7	120.01 (13)	C12—C13—H13	119.8
C5—C6—H6	120.0	C15—C14—C13	120.65 (13)
C7—C6—H6	120.0	C15—C14—H14	119.7
N1—C7—C6	119.03 (12)	C13—C14—H14	119.7
N1—C7—C2	121.49 (11)	C14—C15—C16	119.52 (13)
C6—C7—C2	119.47 (12)	C14—C15—H15	120.2
N1—C8—N2	126.28 (12)	C16—C15—H15	120.2
N1—C8—C10	118.73 (11)	C15—C16—C17	119.99 (13)
N2—C8—C10	114.98 (11)	C15—C16—H16	120.0
S1—C9—H9A	109.5	C17—C16—H16	120.0
S1—C9—H9B	109.5	C16—C17—C12	120.92 (12)
H9A—C9—H9B	109.5	C16—C17—H17	119.5
S1—C9—H9C	109.5	C12—C17—H17	119.5
H9A—C9—H9C	109.5	C8—N1—C7	117.30 (11)
H9B—C9—H9C	109.5	C1—N2—C8	116.95 (11)
C8—C10—C11	115.00 (10)	C11—O1—H1	109.5
C8—C10—H10A	108.5	C1—S1—C9	102.08 (7)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	2.12	2.7531 (15)	134