Crystal structure of 2-[4-(methyl-sulfan-yl)quinazolin-2-yl]-1-phenyl-ethanol.

In the mol-ecule of the title compound, C17H16N2OS, the almost planar methyl-sulfanylquinazoline group [the methyl C atom deviates by 0.032 (2) Å from the plane through the ring system] forms an inter-planar angle of 76.26 (4)° with the plane of the phenyl group. An intra-molecular O-H⋯N hydrogen bond is present between the quinazoline and hy-droxy groups. In the crystal, mol-ecules are stacked along the b-axis direction.

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 crystal structures of related compounds, see: Alshammari et al. (2014a ▶,b ▶).

Experimental

Crystal data

C17H16N2OS

M = 296.38

Monoclinic,

a = 15.6142 (3) Å

b = 5.6142 (1) Å

c = 17.2355 (3) Å

β = 101.138 (2)°

V = 1482.43 (5) Å3

Z = 4

Cu Kα radiation

μ = 1.93 mm−1

T = 293 K

0.32 × 0.19 × 0.14 mm

Data collection

Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014 ▶) T min = 0.867, T max = 1.000

9606 measured reflections

2938 independent reflections

2688 reflections with I > 2σ(I)

R int = 0.014

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.094

S = 1.06

2938 reflections

192 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.28 e Å−3

Data collection: CrysAlis PRO (Agilent, 2014 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS2013 (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 ▶).

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536814019990/gg2141sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814019990/gg2141Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814019990/gg2141Isup3.cml

Click here for additional data file.

17 16 2 . DOI: 10.1107/S1600536814019990/gg2141fig1.tif

A mol­ecule of C17H16N2OS with atom labels and 50% probability displacement ellipsoids for nonhydrogen atoms.

Click here for additional data file.

b . DOI: 10.1107/S1600536814019990/gg2141fig2.tif

Crystal structure packing viewed down the b axis.

CCDC reference: 1022918

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

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) Å3	Block, colourless
Z = 4	0.32 × 0.19 × 0.14 mm

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 on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.032	H-atom parameters constrained
wR(F2) = 0.094	w = 1/[σ2(Fo2) + (0.0507P)2 + 0.2343P] where P = (Fo2 + 2Fc2)/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

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.

	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)

	U11	U22	U33	U12	U13	U23
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)

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)

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

Table 1

Hydrogen-bond geometry (Å, °)

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