3-Isopropyl-2-p-tol-yloxy-5,6,7,8-tetra-hydro-1-benzothieno[2,3-d]pyrimidin-4(3H)-one.

In the title compound, C(20)H(22)N(2)O(2)S, the central thieno-pyrimidine ring system is essentially planar, with a maximum displacement of 0.023 (2) Å. The attached cyclo-hexene ring is disordered over two possible conformations, with an occupancy ratio of 0.776 (12):0.224 (12). Neither inter-molecular hydrogen-bonding inter-actions nor π-π stacking inter-actions are present in the crystal structure. The mol-ecular conformation and crystal packing are stabilized by three intra-molecular C-H⋯O hydrogen bonds and two C-H⋯π inter-actions.

Related literature

For the biological activity of thienopyrimidin-4(3H)-one derivatives, see: De Laszlo et al. (1992a ▶,b ▶); Taguchi et al. (1993a ▶,b ▶); Walter (1999a ▶,b ▶,c ▶,d ▶); Walter & Zeun (2004 ▶); Ding et al. (2004 ▶); Santagati et al. (2003 ▶); Abbott GmbH Co KG (2004a ▶, 2004b ▶); Waehaelae et al. (2004a ▶,b ▶); Ford et al. (2004a ▶,b ▶); Duval et al. (2005 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶). For related structures, see: Xie et al. (2008 ▶); Xu et al. (2005 ▶); Zeng et al. (2005 ▶, 2006 ▶, 2007 ▶, 2008 ▶); Wang et al. (2006 ▶, 2007 ▶, 2008 ▶); Zheng et al. (2007 ▶).

Experimental

Crystal data

C20H22N2O2S

M = 354.47

Monoclinic,

a = 13.2367 (7) Å

b = 5.7493 (3) Å

c = 13.4306 (7) Å

β = 115.858 (4)°

V = 919.76 (8) Å3

Z = 2

Mo Kα radiation

μ = 0.19 mm−1

T = 298 K

0.20 × 0.10 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.963, T max = 0.981

6373 measured reflections

3920 independent reflections

3370 reflections with I > 2σ(I)

R int = 0.079

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.141

S = 1.01

3920 reflections

248 parameters

16 restraints

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.32 e Å−3

Absolute structure: Flack (1983 ▶), 1702 Freidel pairs

Flack parameter: 0.16 (10)

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAIn class="Chemical">NT program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809014962/at2765sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809014962/at2765Isup2.hkl

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

C20H22N2O2S	F(000) = 376
Mr = 354.47	Dx = 1.280 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 2048 reflections
a = 13.2367 (7) Å	θ = 2.9–24.5°
b = 5.7493 (3) Å	µ = 0.19 mm−1
c = 13.4306 (7) Å	T = 298 K
β = 115.858 (4)°	Block, colourless
V = 919.76 (8) Å3	0.20 × 0.10 × 0.10 mm
Z = 2

Bruker SMART CCD area-detector diffractometer	3920 independent reflections
Radiation source: fine-focus sealed tube	3370 reflections with I > 2σ(I)
graphite	Rint = 0.079
φ and ω scans	θmax = 27.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→16
Tmin = 0.963, Tmax = 0.981	k = −7→7
6373 measured reflections	l = −17→15

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.057	H-atom parameters constrained
wR(F2) = 0.141	w = 1/[σ2(Fo2) + (0.0798P)2] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
3920 reflections	Δρmax = 0.20 e Å−3
248 parameters	Δρmin = −0.32 e Å−3
16 restraints	Absolute structure: Flack (1983), 1702 Freidel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.16 (10)

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	Occ. (<1)
C1	0.20878 (19)	0.6656 (5)	0.88050 (19)	0.0448 (6)
C2	0.0948 (2)	0.6877 (6)	0.8794 (2)	0.0563 (7)
H2A	0.0446	0.7700	0.8132	0.068*	0.776 (12)
H2B	0.0639	0.5339	0.8776	0.068*	0.776 (12)
H2C	0.0817	0.5593	0.9191	0.068*	0.224 (12)
H2D	0.0370	0.6849	0.8037	0.068*	0.224 (12)
C3	0.1018 (4)	0.8162 (11)	0.9796 (5)	0.0662 (16)	0.776 (12)
H3A	0.1348	0.7157	1.0439	0.079*	0.776 (12)
H3B	0.0268	0.8576	0.9693	0.079*	0.776 (12)
C4	0.1717 (4)	1.0336 (10)	0.9996 (6)	0.0690 (17)	0.776 (12)
H4A	0.1703	1.1175	1.0616	0.083*	0.776 (12)
H4B	0.1383	1.1329	0.9349	0.083*	0.776 (12)
C3'	0.0904 (12)	0.916 (2)	0.9334 (14)	0.061 (5)	0.224 (12)
H3'1	0.0829	1.0405	0.8817	0.073*	0.224 (12)
H3'2	0.0230	0.9169	0.9448	0.073*	0.224 (12)
C4'	0.1882 (9)	0.974 (5)	1.0420 (11)	0.068 (6)	0.224 (12)
H4'1	0.1965	0.8556	1.0964	0.081*	0.224 (12)
H4'2	0.1758	1.1224	1.0692	0.081*	0.224 (12)
C5	0.2932 (2)	0.9853 (6)	1.0236 (3)	0.0615 (8)
H5A	0.3283	1.1265	1.0144	0.074*	0.776 (12)
H5B	0.3346	0.9322	1.0993	0.074*	0.776 (12)
H5C	0.2996	1.1376	0.9958	0.074*	0.224 (12)
H5D	0.3578	0.9636	1.0943	0.074*	0.224 (12)
C6	0.2953 (2)	0.8022 (5)	0.9451 (2)	0.0489 (6)
C7	0.3471 (2)	0.5369 (5)	0.8298 (2)	0.0457 (6)
C8	0.23832 (18)	0.5102 (5)	0.81357 (19)	0.0419 (5)
C9	0.1665 (2)	0.3547 (5)	0.7278 (2)	0.0440 (5)
C10	0.33155 (19)	0.2882 (5)	0.6970 (2)	0.0472 (6)
C11	0.1476 (2)	0.1089 (5)	0.5680 (2)	0.0476 (6)
H11	0.0727	0.1104	0.5658	0.057*
C12	0.1818 (3)	−0.1432 (6)	0.5773 (3)	0.0763 (10)
H12A	0.2536	−0.1556	0.5760	0.114*
H12B	0.1269	−0.2287	0.5163	0.114*
H12C	0.1867	−0.2060	0.6455	0.114*
C13	0.1348 (3)	0.2214 (6)	0.4619 (2)	0.0640 (8)
H13A	0.1085	0.3781	0.4587	0.096*
H13B	0.0817	0.1349	0.4001	0.096*
H13C	0.2061	0.2229	0.4591	0.096*
C14	0.4833 (2)	0.1798 (5)	0.6585 (2)	0.0515 (7)
C15	0.5521 (3)	0.0051 (7)	0.7178 (3)	0.0704 (9)
H15	0.5252	−0.1141	0.7466	0.084*
C16	0.6628 (3)	0.0076 (7)	0.7348 (3)	0.0743 (9)
H16	0.7098	−0.1137	0.7741	0.089*
C17	0.7055 (2)	0.1829 (6)	0.6956 (2)	0.0592 (8)
C18	0.6321 (3)	0.3536 (7)	0.6344 (3)	0.0721 (9)
H18	0.6583	0.4727	0.6050	0.086*
C19	0.5207 (3)	0.3543 (6)	0.6149 (3)	0.0710 (9)
H19	0.4724	0.4715	0.5730	0.085*
C20	0.8275 (2)	0.1872 (10)	0.7183 (3)	0.0936 (15)
H20A	0.8639	0.3178	0.7646	0.140*
H20B	0.8332	0.2006	0.6496	0.140*
H20C	0.8632	0.0460	0.7549	0.140*
N1	0.22102 (15)	0.2496 (4)	0.66777 (15)	0.0435 (4)
N2	0.39874 (17)	0.4226 (4)	0.77485 (19)	0.0524 (6)
O2	0.36853 (15)	0.1676 (4)	0.63340 (17)	0.0689 (7)
O1	0.06852 (14)	0.3137 (4)	0.70296 (16)	0.0607 (6)
S1	0.41623 (5)	0.74703 (15)	0.92707 (6)	0.0585 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0409 (13)	0.0542 (15)	0.0392 (12)	0.0072 (10)	0.0172 (10)	0.0072 (11)
C2	0.0453 (14)	0.068 (2)	0.0600 (16)	0.0029 (12)	0.0267 (12)	−0.0012 (14)
C3	0.062 (3)	0.086 (4)	0.062 (3)	−0.003 (2)	0.038 (2)	−0.010 (3)
C4	0.075 (3)	0.074 (4)	0.070 (4)	0.005 (2)	0.042 (3)	−0.014 (3)
C3'	0.053 (7)	0.072 (8)	0.060 (8)	0.002 (6)	0.026 (6)	0.000 (6)
C4'	0.075 (9)	0.081 (10)	0.056 (9)	0.012 (6)	0.036 (7)	0.012 (7)
C5	0.0554 (16)	0.071 (2)	0.0553 (16)	0.0041 (14)	0.0213 (13)	−0.0128 (15)
C6	0.0409 (12)	0.0616 (17)	0.0410 (12)	0.0051 (11)	0.0149 (10)	−0.0014 (12)
C7	0.0371 (13)	0.0556 (15)	0.0383 (12)	0.0036 (11)	0.0107 (10)	−0.0022 (11)
C8	0.0347 (11)	0.0508 (13)	0.0373 (12)	0.0014 (10)	0.0130 (10)	0.0026 (10)
C9	0.0369 (12)	0.0502 (14)	0.0449 (13)	0.0016 (10)	0.0179 (10)	0.0058 (11)
C10	0.0360 (11)	0.0563 (16)	0.0490 (13)	0.0013 (11)	0.0182 (10)	−0.0032 (12)
C11	0.0381 (13)	0.0495 (15)	0.0485 (14)	−0.0052 (11)	0.0127 (11)	−0.0059 (12)
C12	0.095 (3)	0.0463 (17)	0.072 (2)	−0.0096 (16)	0.0220 (19)	0.0016 (16)
C13	0.0728 (18)	0.0565 (18)	0.0483 (15)	0.0039 (15)	0.0130 (13)	−0.0016 (14)
C14	0.0381 (13)	0.0631 (18)	0.0561 (15)	−0.0044 (11)	0.0232 (12)	−0.0184 (13)
C15	0.0602 (18)	0.075 (2)	0.082 (2)	−0.0034 (17)	0.0366 (17)	0.0130 (19)
C16	0.0570 (18)	0.083 (2)	0.077 (2)	0.0165 (17)	0.0243 (16)	0.0157 (19)
C17	0.0473 (14)	0.085 (2)	0.0514 (15)	−0.0026 (14)	0.0276 (12)	−0.0128 (15)
C18	0.0622 (19)	0.085 (2)	0.076 (2)	−0.0121 (18)	0.0372 (17)	0.0070 (18)
C19	0.0608 (18)	0.067 (2)	0.083 (2)	0.0070 (16)	0.0292 (17)	0.0075 (18)
C20	0.0496 (17)	0.166 (5)	0.073 (2)	0.002 (2)	0.0332 (16)	−0.020 (3)
N1	0.0338 (9)	0.0498 (11)	0.0439 (10)	−0.0019 (10)	0.0143 (8)	−0.0033 (10)
N2	0.0319 (10)	0.0662 (15)	0.0566 (13)	−0.0020 (10)	0.0169 (9)	−0.0152 (11)
O2	0.0398 (10)	0.0937 (17)	0.0744 (13)	−0.0097 (10)	0.0261 (9)	−0.0374 (12)
O1	0.0361 (9)	0.0808 (15)	0.0670 (11)	−0.0103 (9)	0.0242 (8)	−0.0142 (11)
S1	0.0359 (3)	0.0722 (5)	0.0603 (4)	−0.0040 (3)	0.0144 (3)	−0.0216 (4)

C1—C6	1.347 (4)	C9—O1	1.213 (3)
C1—C8	1.437 (4)	C9—N1	1.429 (3)
C1—C2	1.508 (3)	C10—N2	1.292 (3)
C2—C3	1.502 (5)	C10—O2	1.348 (3)
C2—C3'	1.515 (10)	C10—N1	1.358 (3)
C2—H2A	0.9700	C11—N1	1.503 (3)
C2—H2B	0.9700	C11—C13	1.506 (4)
C2—H2C	0.9700	C11—C12	1.508 (5)
C2—H2D	0.9700	C11—H11	0.9800
C3—C4	1.508 (7)	C12—H12A	0.9600
C3—H3A	0.9700	C12—H12B	0.9600
C3—H3B	0.9700	C12—H12C	0.9600
C4—C5	1.521 (5)	C13—H13A	0.9600
C4—H4A	0.9700	C13—H13B	0.9600
C4—H4B	0.9700	C13—H13C	0.9600
C3'—C4'	1.505 (10)	C14—C15	1.356 (5)
C3'—H3'1	0.9700	C14—C19	1.359 (4)
C3'—H3'2	0.9700	C14—O2	1.407 (3)
C4'—C5	1.515 (9)	C15—C16	1.382 (4)
C4'—H4'1	0.9700	C15—H15	0.9300
C4'—H4'2	0.9700	C16—C17	1.368 (5)
C5—C6	1.499 (4)	C16—H16	0.9300
C5—H5A	0.9700	C17—C18	1.373 (5)
C5—H5B	0.9700	C17—C20	1.508 (4)
C5—H5C	0.9700	C18—C19	1.381 (4)
C5—H5D	0.9700	C18—H18	0.9300
C6—S1	1.749 (3)	C19—H19	0.9300
C7—C8	1.368 (3)	C20—H20A	0.9600
C7—N2	1.372 (3)	C20—H20B	0.9600
C7—S1	1.721 (3)	C20—H20C	0.9600
C8—C9	1.440 (4)
C6—C1—C8	112.2 (2)	H5A—C5—H5D	88.0
C6—C1—C2	121.6 (2)	H5B—C5—H5D	23.0
C8—C1—C2	126.2 (2)	H5C—C5—H5D	107.8
C3—C2—C1	111.2 (3)	C1—C6—C5	126.2 (2)
C3—C2—C3'	31.2 (6)	C1—C6—S1	112.19 (19)
C1—C2—C3'	108.4 (7)	C5—C6—S1	121.6 (2)
C3—C2—H2A	109.4	C8—C7—N2	126.7 (2)
C1—C2—H2A	109.4	C8—C7—S1	111.93 (19)
C3'—C2—H2A	82.1	N2—C7—S1	121.34 (18)
C3—C2—H2B	109.4	C7—C8—C1	112.7 (2)
C1—C2—H2B	109.4	C7—C8—C9	118.6 (2)
C3'—C2—H2B	134.4	C1—C8—C9	128.4 (2)
H2A—C2—H2B	108.0	O1—C9—N1	120.3 (2)
C3—C2—H2C	80.7	O1—C9—C8	126.4 (2)
C1—C2—H2C	110.4	N1—C9—C8	113.2 (2)
C3'—C2—H2C	110.1	N2—C10—O2	120.6 (2)
H2A—C2—H2C	131.4	N2—C10—N1	127.4 (2)
H2B—C2—H2C	31.3	O2—C10—N1	112.1 (2)
C3—C2—H2D	131.3	N1—C11—C13	112.0 (2)
C1—C2—H2D	109.7	N1—C11—C12	112.9 (2)
C3'—C2—H2D	109.9	C13—C11—C12	113.4 (3)
H2A—C2—H2D	30.2	N1—C11—H11	105.9
H2B—C2—H2D	80.0	C13—C11—H11	105.9
H2C—C2—H2D	108.4	C12—C11—H11	105.9
C2—C3—C4	111.1 (5)	C11—C12—H12A	109.5
C2—C3—H3A	109.4	C11—C12—H12B	109.5
C4—C3—H3A	109.4	H12A—C12—H12B	109.5
C2—C3—H3B	109.4	C11—C12—H12C	109.5
C4—C3—H3B	109.4	H12A—C12—H12C	109.5
H3A—C3—H3B	108.0	H12B—C12—H12C	109.5
C3—C4—C5	113.3 (4)	C11—C13—H13A	109.5
C3—C4—H4A	108.9	C11—C13—H13B	109.5
C5—C4—H4A	108.9	H13A—C13—H13B	109.5
C3—C4—H4B	108.9	C11—C13—H13C	109.5
C5—C4—H4B	108.9	H13A—C13—H13C	109.5
H4A—C4—H4B	107.7	H13B—C13—H13C	109.5
C4'—C3'—C2	117.3 (15)	C15—C14—C19	121.5 (3)
C4'—C3'—H3'1	108.0	C15—C14—O2	118.8 (3)
C2—C3'—H3'1	108.0	C19—C14—O2	119.4 (3)
C4'—C3'—H3'2	108.0	C14—C15—C16	118.8 (3)
C2—C3'—H3'2	108.0	C14—C15—H15	120.6
H3'1—C3'—H3'2	107.2	C16—C15—H15	120.6
C3'—C4'—C5	108.3 (10)	C17—C16—C15	122.0 (3)
C3'—C4'—H4'1	110.0	C17—C16—H16	119.0
C5—C4'—H4'1	110.0	C15—C16—H16	119.0
C3'—C4'—H4'2	110.0	C16—C17—C18	117.0 (3)
C5—C4'—H4'2	110.0	C16—C17—C20	121.3 (3)
H4'1—C4'—H4'2	108.4	C18—C17—C20	121.6 (3)
C6—C5—C4'	112.6 (9)	C17—C18—C19	122.2 (3)
C6—C5—C4	108.8 (3)	C17—C18—H18	118.9
C4'—C5—C4	23.5 (6)	C19—C18—H18	118.9
C6—C5—H5A	109.9	C14—C19—C18	118.4 (3)
C4'—C5—H5A	125.5	C14—C19—H19	120.8
C4—C5—H5A	109.9	C18—C19—H19	120.8
C6—C5—H5B	109.9	C17—C20—H20A	109.5
C4'—C5—H5B	87.4	C17—C20—H20B	109.5
C4—C5—H5B	109.9	H20A—C20—H20B	109.5
H5A—C5—H5B	108.3	C17—C20—H20C	109.5
C6—C5—H5C	109.4	H20A—C20—H20C	109.5
C4'—C5—H5C	110.0	H20B—C20—H20C	109.5
C4—C5—H5C	90.9	C10—N1—C9	120.8 (2)
H5A—C5—H5C	21.3	C10—N1—C11	122.9 (2)
H5B—C5—H5C	125.7	C9—N1—C11	116.21 (18)
C6—C5—H5D	108.6	C10—N2—C7	113.1 (2)
C4'—C5—H5D	108.3	C10—O2—C14	118.4 (2)
C4—C5—H5D	129.0	C7—S1—C6	90.97 (12)
C6—C1—C2—C3	−17.9 (5)	C19—C14—C15—C16	0.6 (5)
C8—C1—C2—C3	164.4 (4)	O2—C14—C15—C16	174.8 (3)
C6—C1—C2—C3'	15.2 (8)	C14—C15—C16—C17	1.4 (5)
C8—C1—C2—C3'	−162.5 (8)	C15—C16—C17—C18	−2.5 (5)
C1—C2—C3—C4	46.7 (6)	C15—C16—C17—C20	177.8 (3)
C3'—C2—C3—C4	−44.0 (11)	C16—C17—C18—C19	1.7 (5)
C2—C3—C4—C5	−62.5 (8)	C20—C17—C18—C19	−178.6 (3)
C3—C2—C3'—C4'	53.3 (13)	C15—C14—C19—C18	−1.4 (5)
C1—C2—C3'—C4'	−47.5 (19)	O2—C14—C19—C18	−175.5 (3)
C2—C3'—C4'—C5	61 (3)	C17—C18—C19—C14	0.2 (5)
C3'—C4'—C5—C6	−39 (2)	N2—C10—N1—C9	−2.7 (4)
C3'—C4'—C5—C4	46.5 (12)	O2—C10—N1—C9	177.7 (2)
C3—C4—C5—C6	43.0 (7)	N2—C10—N1—C11	173.4 (3)
C3—C4—C5—C4'	−61 (2)	O2—C10—N1—C11	−6.3 (4)
C8—C1—C6—C5	179.2 (3)	O1—C9—N1—C10	−177.9 (3)
C2—C1—C6—C5	1.2 (4)	C8—C9—N1—C10	3.8 (3)
C8—C1—C6—S1	0.0 (3)	O1—C9—N1—C11	5.8 (4)
C2—C1—C6—S1	−178.0 (2)	C8—C9—N1—C11	−172.6 (2)
C4'—C5—C6—C1	11.4 (9)	C13—C11—N1—C10	−64.3 (3)
C4—C5—C6—C1	−13.4 (5)	C12—C11—N1—C10	65.2 (3)
C4'—C5—C6—S1	−169.5 (9)	C13—C11—N1—C9	112.0 (3)
C4—C5—C6—S1	165.8 (3)	C12—C11—N1—C9	−118.6 (3)
N2—C7—C8—C1	−176.8 (3)	O2—C10—N2—C7	178.4 (3)
S1—C7—C8—C1	0.7 (3)	N1—C10—N2—C7	−1.2 (4)
N2—C7—C8—C9	−2.7 (4)	C8—C7—N2—C10	4.0 (4)
S1—C7—C8—C9	174.81 (19)	S1—C7—N2—C10	−173.3 (2)
C6—C1—C8—C7	−0.4 (3)	N2—C10—O2—C14	4.1 (4)
C2—C1—C8—C7	177.4 (2)	N1—C10—O2—C14	−176.3 (2)
C6—C1—C8—C9	−173.8 (2)	C15—C14—O2—C10	98.6 (3)
C2—C1—C8—C9	4.1 (4)	C19—C14—O2—C10	−87.0 (3)
C7—C8—C9—O1	−179.5 (3)	C8—C7—S1—C6	−0.6 (2)
C1—C8—C9—O1	−6.5 (4)	N2—C7—S1—C6	177.0 (2)
C7—C8—C9—N1	−1.3 (3)	C1—C6—S1—C7	0.4 (2)
C1—C8—C9—N1	171.7 (2)	C5—C6—S1—C7	−178.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13C···O2	0.96	2.41	2.959 (4)	116
C12—H12A···O2	0.96	2.31	2.871 (4)	117
C11—H11···O1	0.98	2.20	2.725 (3)	112
C12—H12C···Cg1i	0.96	2.94	3.838 (4)	156
C12—H12C···Cg2i	0.96	2.72	3.413 (4)	130

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13C⋯O2	0.96	2.41	2.959 (4)	116
C12—H12A⋯O2	0.96	2.31	2.871 (4)	117
C11—H11⋯O1	0.98	2.20	2.725 (3)	112
C12—H12C⋯Cg1i	0.96	2.94	3.838 (4)	156
C12—H12C⋯Cg2i	0.96	2.72	3.413 (4)	130

Symmetry code: (i) . Cg1 and Cg2 are the centroids of the thio­phene (S1/C1/C6–C8) and pyrimidine (N1/N2/C7–C10) rings, respectively.