2,3-Dihydro-pyrrolo-[2,1-b]quinazoline-9(1H)-thione.

In the crystal, mol-ecules of the title compound, C(11)H(10)N(2)S, are connected by C-H⋯N inter-actions around threefold axes. Furthermore, they form stacks along the c axis showing π-π inter-actions between pyrimidine rings [centroid-centroid distance = 3.721 (1) Å]. The central ring is essentially planar with an r.m.s. deviation of 0.007 Å. The five-membered ring adopts an envelope conformation with the flap atom deviating by 0.241 (4) Å from the mean plane (r.m.s. deviation = 0.002 Å) through the other four ring atoms.

Related literature

For the synthesis of 2,3-dihydro-1H,9H-pyrrolo­[2,1-b]quinazolin-9-one and the title compound, see: Abduraza­kov et al. (2007 ▶); Shakhidoyatov & Kadyrov (1977 ▶); Elmuradov et al. (2010 ▶). For related structures, see Elmuradov et al. (2010 ▶); Turgunov et al. (1995 ▶).

Experimental

Crystal data

C11H10N2S

M = 202.27

Trigonal,

a = 26.206 (1) Å

c = 7.441 (2) Å

V = 4425.5 (12) Å3

Z = 18

Cu Kα radiation

μ = 2.57 mm−1

T = 295 K

0.65 × 0.25 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur Ruby diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.601, T max = 1.000

5753 measured reflections

1379 independent reflections

1305 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.078

S = 1.06

1379 reflections

128 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.19 e Å−3

Absolute structure: Flack (1983 ▶), 501 Friedel pairs

Flack parameter: −0.003 (19)

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP (Bruker, 1998 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812021228/bt5913sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812021228/bt5913Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812021228/bt5913Isup3.cml

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

C11H10N2S	Dx = 1.366 Mg m−3
Mr = 202.27	Melting point: 411 K
Trigonal, R3c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: R 3 -2"c	Cell parameters from 2338 reflections
a = 26.206 (1) Å	θ = 3.4–66.8°
c = 7.441 (2) Å	µ = 2.57 mm−1
V = 4425.5 (12) Å3	T = 295 K
Z = 18	Prism, yellow
F(000) = 1908	0.65 × 0.25 × 0.20 mm

Oxford Diffraction Xcalibur Ruby diffractometer	1379 independent reflections
Radiation source: Enhance (Cu) X-ray Source	1305 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
Detector resolution: 10.2576 pixels mm-1	θmax = 66.8°, θmin = 3.4°
ω scans	h = −28→31
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −31→31
Tmin = 0.601, Tmax = 1.000	l = −8→8
5753 measured reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.029	w = 1/[σ2(Fo2) + (0.0613P)2 + 0.028P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.078	(Δ/σ)max < 0.001
S = 1.06	Δρmax = 0.16 e Å−3
1379 reflections	Δρmin = −0.19 e Å−3
128 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraint	Extinction coefficient: 0.00144 (11)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 501 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: −0.003 (19)

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.

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 > σ(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	0.89225 (2)	0.23959 (3)	0.13284 (10)	0.0588 (2)
N1	0.71400 (8)	0.21624 (8)	0.2807 (3)	0.0562 (5)
C2	0.72288 (9)	0.17396 (9)	0.2343 (3)	0.0480 (4)
N3	0.77699 (7)	0.18140 (7)	0.1857 (2)	0.0445 (4)
C4	0.82758 (8)	0.23443 (9)	0.1852 (3)	0.0451 (4)
C4A	0.81976 (9)	0.28375 (9)	0.2345 (3)	0.0477 (4)
C5	0.86723 (10)	0.34181 (10)	0.2392 (4)	0.0614 (5)
H5A	0.9050	0.3495	0.2105	0.074*
C6	0.85814 (13)	0.38726 (11)	0.2857 (5)	0.0765 (8)
H6A	0.8898	0.4256	0.2880	0.092*
C7	0.80209 (14)	0.37644 (12)	0.3296 (5)	0.0827 (9)
H7A	0.7964	0.4076	0.3604	0.099*
C8	0.75527 (11)	0.32025 (12)	0.3276 (5)	0.0746 (7)
H8A	0.7180	0.3135	0.3581	0.090*
C8A	0.76270 (10)	0.27240 (9)	0.2803 (3)	0.0528 (5)
C9	0.67738 (10)	0.11011 (10)	0.2275 (4)	0.0601 (5)
H9A	0.6436	0.1040	0.1570	0.072*
H9B	0.6642	0.0947	0.3475	0.072*
C10	0.70825 (10)	0.08040 (10)	0.1391 (4)	0.0670 (6)
H10A	0.6999	0.0450	0.2044	0.080*
H10B	0.6949	0.0697	0.0161	0.080*
C11	0.77385 (10)	0.12481 (9)	0.1437 (4)	0.0548 (5)
H11A	0.7934	0.1146	0.2356	0.066*
H11B	0.7920	0.1267	0.0283	0.066*

	U11	U22	U33	U12	U13	U23
S1	0.0415 (3)	0.0673 (4)	0.0720 (3)	0.0306 (2)	0.0040 (2)	−0.0012 (3)
N1	0.0407 (8)	0.0548 (10)	0.0767 (12)	0.0265 (8)	−0.0002 (8)	0.0031 (9)
C2	0.0375 (9)	0.0509 (10)	0.0541 (10)	0.0210 (8)	−0.0041 (8)	0.0011 (9)
N3	0.0422 (8)	0.0457 (9)	0.0480 (8)	0.0238 (7)	−0.0023 (6)	0.0014 (7)
C4	0.0420 (9)	0.0512 (11)	0.0442 (9)	0.0250 (9)	−0.0033 (8)	0.0018 (8)
C4A	0.0444 (10)	0.0472 (10)	0.0541 (10)	0.0249 (8)	−0.0033 (8)	0.0033 (9)
C5	0.0499 (11)	0.0504 (11)	0.0791 (14)	0.0215 (9)	−0.0041 (11)	0.0013 (11)
C6	0.0686 (15)	0.0437 (12)	0.110 (2)	0.0229 (12)	−0.0094 (14)	−0.0012 (13)
C7	0.0838 (17)	0.0545 (13)	0.124 (3)	0.0454 (13)	−0.0099 (18)	−0.0084 (15)
C8	0.0615 (14)	0.0649 (14)	0.112 (2)	0.0429 (12)	−0.0006 (15)	−0.0018 (15)
C8A	0.0485 (11)	0.0482 (11)	0.0667 (12)	0.0279 (9)	−0.0062 (10)	0.0009 (9)
C9	0.0429 (10)	0.0519 (11)	0.0752 (13)	0.0160 (9)	−0.0014 (10)	−0.0002 (11)
C10	0.0616 (14)	0.0464 (11)	0.0850 (16)	0.0211 (10)	−0.0043 (13)	−0.0053 (11)
C11	0.0601 (12)	0.0512 (11)	0.0592 (11)	0.0325 (10)	−0.0004 (11)	−0.0029 (12)

S1—C4	1.6771 (18)	C6—H6A	0.9300
N1—C2	1.288 (3)	C7—C8	1.366 (4)
N1—C8A	1.384 (3)	C7—H7A	0.9300
C2—N3	1.380 (3)	C8—C8A	1.406 (3)
C2—C9	1.493 (3)	C8—H8A	0.9300
N3—C4	1.359 (3)	C9—C10	1.524 (3)
N3—C11	1.477 (3)	C9—H9A	0.9700
C4—C4A	1.453 (3)	C9—H9B	0.9700
C4A—C5	1.404 (3)	C10—C11	1.520 (3)
C4A—C8A	1.413 (3)	C10—H10A	0.9700
C5—C6	1.371 (4)	C10—H10B	0.9700
C5—H5A	0.9300	C11—H11A	0.9700
C6—C7	1.388 (4)	C11—H11B	0.9700
C2—N1—C8A	116.55 (17)	C7—C8—H8A	119.6
N1—C2—N3	124.32 (18)	C8A—C8—H8A	119.6
N1—C2—C9	125.92 (19)	N1—C8A—C8	118.8 (2)
N3—C2—C9	109.75 (18)	N1—C8A—C4A	122.71 (18)
C4—N3—C2	123.61 (16)	C8—C8A—C4A	118.5 (2)
C4—N3—C11	124.21 (16)	C2—C9—C10	104.87 (19)
C2—N3—C11	112.11 (16)	C2—C9—H9A	110.8
N3—C4—C4A	114.17 (16)	C10—C9—H9A	110.8
N3—C4—S1	120.86 (15)	C2—C9—H9B	110.8
C4A—C4—S1	124.97 (16)	C10—C9—H9B	110.8
C5—C4A—C8A	119.56 (19)	H9A—C9—H9B	108.8
C5—C4A—C4	121.83 (19)	C11—C10—C9	106.58 (18)
C8A—C4A—C4	118.61 (18)	C11—C10—H10A	110.4
C6—C5—C4A	120.2 (2)	C9—C10—H10A	110.4
C6—C5—H5A	119.9	C11—C10—H10B	110.4
C4A—C5—H5A	119.9	C9—C10—H10B	110.4
C5—C6—C7	120.5 (2)	H10A—C10—H10B	108.6
C5—C6—H6A	119.7	N3—C11—C10	104.32 (18)
C7—C6—H6A	119.7	N3—C11—H11A	110.9
C8—C7—C6	120.4 (2)	C10—C11—H11A	110.9
C8—C7—H7A	119.8	N3—C11—H11B	110.9
C6—C7—H7A	119.8	C10—C11—H11B	110.9
C7—C8—C8A	120.9 (2)	H11A—C11—H11B	108.9

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···N1i	0.93	2.61	3.464 (4)	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7A⋯N1i	0.93	2.61	3.464 (4)	153

Symmetry code: (i) .