Absolute configuration of (1S,2S)-3-methyl-2-phenyl-2,3-dihydro-thia-zolo[2,3-b]quinazolin-5-one.

The absolute structure of the molecule in the crystal of the title compound, C(17)H(14)N(2)OS, was determined by the refinement of the Flack parameter to 0.0 (2) based on 1011 Friedel pairs. The quinazoline ring is essentially planar, with a maximum deviation of 0.037 (2) Å. The thia-zole ring is distorted from planarity [maximum deviation = 0.168 (2) Å] and adopts a slightly twisted envelope conformation, with the C atom as the flap atom. The central thia-zole ring makes dihedral angles of 7.01 (8) and 76.80 (10)° with the quinazoline and phenyl rings, respectively. The corresponding angle between the quinazoline and phenyl rings is 3.74 (9)°. In the crystal, there are no classical hydrogen bonds but stabilization is provided by weak C-H⋯π inter-actions, involving the centroids of the phenyl rings.

Related literature

For details and applications of quinazoline derivatives, see: Ghorab et al. (2010a ▶,b ▶,c ▶). For related crystal structures, see: Al-Salahi et al. (2012 ▶); Priya et al. (2011 ▶); Liu et al. (2010 ▶). For ring conformations, see: Cremer & Pople (1975 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C17H14N2OS

M = 294.36

Orthorhombic,

a = 8.4865 (1) Å

b = 10.0846 (2) Å

c = 16.8290 (3) Å

V = 1440.28 (4) Å3

Z = 4

Cu Kα radiation

μ = 1.99 mm−1

T = 296 K

0.96 × 0.64 × 0.51 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.251, T max = 0.431

8654 measured reflections

2637 independent reflections

2521 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.109

S = 1.08

2637 reflections

192 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.23 e Å−3

Absolute structure: Flack (1983 ▶), with 1011 Friedel pairs

Flack parameter: 0.00 (2)

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681200832X/nk2145sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681200832X/nk2145Isup2.hkl

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

C17H14N2OS	F(000) = 616
Mr = 294.36	Dx = 1.358 Mg m−3
Orthorhombic, P212121	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4079 reflections
a = 8.4865 (1) Å	θ = 4.4–71.7°
b = 10.0846 (2) Å	µ = 1.99 mm−1
c = 16.8290 (3) Å	T = 296 K
V = 1440.28 (4) Å3	Block, colourless
Z = 4	0.96 × 0.64 × 0.51 mm

Bruker SMART APEXII CCD diffractometer	2637 independent reflections
Radiation source: fine-focus sealed tube	2521 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
φ and ω scans	θmax = 71.9°, θmin = 5.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −10→10
Tmin = 0.251, Tmax = 0.431	k = −8→12
8654 measured reflections	l = −20→20

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.043	w = 1/[σ2(Fo2) + (0.0729P)2 + 0.0628P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.109	(Δ/σ)max = 0.001
S = 1.08	Δρmax = 0.22 e Å−3
2637 reflections	Δρmin = −0.23 e Å−3
192 parameters	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraints	Extinction coefficient: 0.107 (4)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), with 1011 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.00 (2)

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

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2σ(F2) is used only for calculating R-factors(gt) 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
S1	0.93740 (6)	0.77405 (8)	0.26159 (3)	0.0835 (3)
N1	0.84292 (17)	0.75544 (18)	0.40678 (9)	0.0558 (4)
N2	0.99073 (19)	0.57264 (18)	0.35894 (9)	0.0585 (4)
O1	0.7394 (3)	0.7625 (3)	0.53134 (11)	0.0983 (7)
C3	0.8142 (2)	0.7024 (3)	0.48182 (12)	0.0654 (5)
C10	0.9264 (2)	0.6865 (2)	0.35080 (10)	0.0540 (4)
C9	0.9715 (2)	0.51345 (19)	0.43270 (11)	0.0561 (4)
C12	0.5242 (2)	0.8021 (2)	0.28662 (15)	0.0693 (6)
H12A	0.5479	0.7496	0.3304	0.083*
C11	0.6379 (2)	0.88563 (18)	0.25601 (12)	0.0556 (4)
C4	0.8811 (2)	0.5710 (2)	0.49297 (11)	0.0598 (5)
C13	0.3752 (3)	0.7954 (3)	0.25291 (17)	0.0743 (6)
H13A	0.2993	0.7396	0.2746	0.089*
C5	0.8607 (3)	0.5028 (3)	0.56509 (14)	0.0774 (6)
H5A	0.8007	0.5405	0.6055	0.093*
C14	0.3400 (3)	0.8704 (2)	0.18807 (17)	0.0730 (6)
H14A	0.2396	0.8670	0.1660	0.088*
C16	0.6023 (3)	0.9594 (2)	0.18898 (14)	0.0633 (5)
H16A	0.6783	1.0144	0.1666	0.076*
C6	0.9290 (4)	0.3807 (3)	0.57612 (17)	0.0875 (8)
H6A	0.9131	0.3350	0.6235	0.105*
C1	0.7973 (2)	0.9010 (2)	0.29489 (15)	0.0659 (5)
H1A	0.8396	0.9878	0.2798	0.079*
C15	0.4533 (3)	0.9515 (2)	0.15507 (14)	0.0723 (6)
H15A	0.4299	1.0010	0.1100	0.087*
C8	1.0433 (3)	0.3896 (2)	0.44566 (15)	0.0744 (6)
H8A	1.1052	0.3517	0.4061	0.089*
C2	0.7980 (2)	0.8926 (2)	0.38635 (14)	0.0659 (5)
H2B	0.6911	0.9094	0.4060	0.079*
C17	0.9107 (4)	0.9910 (3)	0.4252 (3)	0.1039 (11)
H17A	0.9070	0.9806	0.4818	0.156*
H17C	0.8802	1.0797	0.4113	0.156*
H17D	1.0160	0.9746	0.4067	0.156*
C7	1.0225 (4)	0.3247 (3)	0.51644 (19)	0.0874 (8)
H7A	1.0707	0.2431	0.5248	0.105*

	U11	U22	U33	U12	U13	U23
S1	0.0541 (3)	0.1285 (5)	0.0680 (3)	0.0297 (3)	0.0168 (2)	0.0362 (3)
N1	0.0436 (7)	0.0702 (9)	0.0535 (8)	0.0037 (6)	−0.0037 (6)	−0.0028 (7)
N2	0.0529 (8)	0.0726 (10)	0.0500 (7)	0.0055 (7)	−0.0055 (6)	−0.0051 (7)
O1	0.1001 (14)	0.1344 (18)	0.0602 (9)	0.0463 (14)	0.0130 (8)	−0.0049 (10)
C3	0.0512 (9)	0.0952 (14)	0.0497 (9)	0.0092 (10)	−0.0022 (8)	−0.0043 (9)
C10	0.0393 (7)	0.0739 (11)	0.0490 (8)	0.0004 (7)	−0.0014 (7)	0.0020 (7)
C9	0.0526 (9)	0.0635 (10)	0.0522 (9)	−0.0071 (7)	−0.0092 (7)	−0.0034 (7)
C12	0.0519 (10)	0.0741 (12)	0.0820 (13)	−0.0033 (8)	−0.0106 (9)	0.0223 (10)
C11	0.0469 (8)	0.0523 (8)	0.0675 (10)	0.0055 (6)	−0.0032 (8)	0.0022 (8)
C4	0.0472 (8)	0.0815 (12)	0.0507 (9)	−0.0083 (8)	−0.0059 (7)	0.0028 (8)
C13	0.0491 (10)	0.0816 (13)	0.0923 (16)	−0.0055 (9)	−0.0084 (10)	0.0104 (12)
C5	0.0615 (12)	0.1126 (18)	0.0579 (11)	−0.0103 (12)	−0.0015 (9)	0.0107 (12)
C14	0.0527 (10)	0.0768 (13)	0.0896 (15)	0.0096 (9)	−0.0178 (11)	−0.0050 (11)
C16	0.0634 (11)	0.0560 (9)	0.0705 (11)	0.0068 (8)	−0.0005 (9)	0.0064 (8)
C6	0.0857 (16)	0.0934 (17)	0.0833 (15)	−0.0174 (14)	−0.0132 (14)	0.0307 (13)
C1	0.0460 (9)	0.0666 (10)	0.0850 (14)	−0.0021 (8)	−0.0040 (9)	0.0180 (10)
C15	0.0745 (13)	0.0697 (11)	0.0727 (12)	0.0158 (10)	−0.0151 (10)	0.0056 (9)
C8	0.0880 (15)	0.0662 (11)	0.0691 (11)	0.0015 (11)	−0.0152 (12)	−0.0065 (9)
C2	0.0505 (9)	0.0676 (11)	0.0795 (13)	0.0061 (8)	−0.0114 (9)	−0.0047 (10)
C17	0.0876 (19)	0.0806 (16)	0.143 (3)	−0.0012 (14)	−0.038 (2)	−0.0195 (18)
C7	0.107 (2)	0.0709 (13)	0.0845 (15)	−0.0052 (13)	−0.0216 (15)	0.0107 (11)

S1—C10	1.7439 (18)	C5—C6	1.374 (5)
S1—C1	1.835 (2)	C5—H5A	0.9300
N1—C10	1.368 (3)	C14—C15	1.379 (4)
N1—C3	1.393 (3)	C14—H14A	0.9300
N1—C2	1.475 (3)	C16—C15	1.390 (3)
N2—C10	1.279 (3)	C16—H16A	0.9300
N2—C9	1.387 (3)	C6—C7	1.399 (5)
O1—C3	1.211 (3)	C6—H6A	0.9300
C3—C4	1.454 (3)	C1—C2	1.542 (3)
C9—C4	1.398 (3)	C1—H1A	0.9800
C9—C8	1.406 (3)	C15—H15A	0.9300
C12—C11	1.380 (3)	C8—C7	1.371 (4)
C12—C13	1.388 (3)	C8—H8A	0.9300
C12—H12A	0.9300	C2—C17	1.526 (3)
C11—C16	1.385 (3)	C2—H2B	0.9800
C11—C1	1.511 (3)	C17—H17A	0.9600
C4—C5	1.406 (3)	C17—H17C	0.9600
C13—C14	1.361 (4)	C17—H17D	0.9600
C13—H13A	0.9300	C7—H7A	0.9300
C10—S1—C1	93.18 (10)	C11—C16—H16A	119.9
C10—N1—C3	121.33 (18)	C15—C16—H16A	119.9
C10—N1—C2	116.71 (17)	C5—C6—C7	120.3 (2)
C3—N1—C2	121.72 (18)	C5—C6—H6A	119.9
C10—N2—C9	115.61 (16)	C7—C6—H6A	119.9
O1—C3—N1	121.6 (2)	C11—C1—C2	115.45 (17)
O1—C3—C4	124.9 (2)	C11—C1—S1	112.12 (16)
N1—C3—C4	113.49 (18)	C2—C1—S1	105.33 (14)
N2—C10—N1	127.10 (17)	C11—C1—H1A	107.9
N2—C10—S1	121.59 (14)	C2—C1—H1A	107.9
N1—C10—S1	111.31 (14)	S1—C1—H1A	107.9
N2—C9—C4	122.34 (19)	C14—C15—C16	120.2 (2)
N2—C9—C8	118.0 (2)	C14—C15—H15A	119.9
C4—C9—C8	119.6 (2)	C16—C15—H15A	119.9
C11—C12—C13	120.9 (2)	C7—C8—C9	120.2 (3)
C11—C12—H12A	119.5	C7—C8—H8A	119.9
C13—C12—H12A	119.5	C9—C8—H8A	119.9
C12—C11—C16	118.68 (18)	N1—C2—C17	110.36 (19)
C12—C11—C1	121.78 (18)	N1—C2—C1	106.58 (17)
C16—C11—C1	119.52 (18)	C17—C2—C1	113.2 (2)
C9—C4—C5	119.4 (2)	N1—C2—H2B	108.9
C9—C4—C3	119.94 (18)	C17—C2—H2B	108.9
C5—C4—C3	120.6 (2)	C1—C2—H2B	108.9
C14—C13—C12	120.0 (2)	C2—C17—H17A	109.5
C14—C13—H13A	120.0	C2—C17—H17C	109.5
C12—C13—H13A	120.0	H17A—C17—H17C	109.5
C6—C5—C4	120.2 (3)	C2—C17—H17D	109.5
C6—C5—H5A	119.9	H17A—C17—H17D	109.5
C4—C5—H5A	119.9	H17C—C17—H17D	109.5
C13—C14—C15	120.0 (2)	C8—C7—C6	120.3 (3)
C13—C14—H14A	120.0	C8—C7—H7A	119.8
C15—C14—H14A	120.0	C6—C7—H7A	119.8
C11—C16—C15	120.1 (2)
C10—N1—C3—O1	−179.4 (2)	C3—C4—C5—C6	−177.7 (2)
C2—N1—C3—O1	6.4 (3)	C12—C13—C14—C15	1.1 (4)
C10—N1—C3—C4	0.1 (3)	C12—C11—C16—C15	1.8 (3)
C2—N1—C3—C4	−174.12 (17)	C1—C11—C16—C15	−176.6 (2)
C9—N2—C10—N1	0.6 (3)	C4—C5—C6—C7	1.6 (4)
C9—N2—C10—S1	−179.34 (13)	C12—C11—C1—C2	−34.8 (3)
C3—N1—C10—N2	−2.2 (3)	C16—C11—C1—C2	143.6 (2)
C2—N1—C10—N2	172.28 (18)	C12—C11—C1—S1	85.8 (2)
C3—N1—C10—S1	177.70 (15)	C16—C11—C1—S1	−95.81 (19)
C2—N1—C10—S1	−7.8 (2)	C10—S1—C1—C11	−105.81 (15)
C1—S1—C10—N2	171.57 (16)	C10—S1—C1—C2	20.52 (15)
C1—S1—C10—N1	−8.37 (15)	C13—C14—C15—C16	−1.6 (4)
C10—N2—C9—C4	3.2 (3)	C11—C16—C15—C14	0.1 (3)
C10—N2—C9—C8	−178.35 (18)	N2—C9—C8—C7	−177.4 (2)
C13—C12—C11—C16	−2.4 (4)	C4—C9—C8—C7	1.2 (3)
C13—C12—C11—C1	176.0 (2)	C10—N1—C2—C17	−99.9 (3)
N2—C9—C4—C5	177.15 (19)	C3—N1—C2—C17	74.6 (3)
C8—C9—C4—C5	−1.3 (3)	C10—N1—C2—C1	23.4 (2)
N2—C9—C4—C3	−5.2 (3)	C3—N1—C2—C1	−162.12 (17)
C8—C9—C4—C3	176.33 (19)	C11—C1—C2—N1	97.6 (2)
O1—C3—C4—C9	−177.2 (2)	S1—C1—C2—N1	−26.69 (19)
N1—C3—C4—C9	3.3 (3)	C11—C1—C2—C17	−140.9 (2)
O1—C3—C4—C5	0.4 (4)	S1—C1—C2—C17	94.8 (2)
N1—C3—C4—C5	−179.06 (19)	C9—C8—C7—C6	0.3 (4)
C11—C12—C13—C14	0.9 (4)	C5—C6—C7—C8	−1.7 (4)
C9—C4—C5—C6	0.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2B···Cg3i	0.98	2.91	3.824 (2)	155
C6—H6A···Cg4ii	0.93	2.81	3.637 (3)	146

Table 1

Hydrogen-bond geometry (Å, °)

Cg3 and Cg4 are the centroids of the C4–C9 and C11–C16 phenyl rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2B⋯Cg3i	0.98	2.91	3.824 (2)	155
C6—H6A⋯Cg4ii	0.93	2.81	3.637 (3)	146

Symmetry codes: (i) ; (ii) .