Ethyl 2-methyl-6-(propan-2-yl-amino)-4-sulfanyl-idene-3H,11H-pyrimido[1,6-c]quinazoline-1-carboxyl-ate.

The title compound, C(18)H(22)N(4)O(2)S, contains a substituted pyrimidine ring fused to both a benzene ring and a substituted thioxopyrimidine ring. The pyrimidine and thioxopyrimidine rings adopt distorted chair conformations. In the crystal, adjacent mol-ecules are linked by pairs of N-H⋯S and N-H⋯O hydrogen bonds to generate centrosymmetric R(2) (2)(8) and R(2) (2)(16) loops, respectively. This combination leads to [100] chains of mol-ecules.

Related literature

For further synthetic details, see: Li et al. (2007 ▶, 2008 ▶); Huang et al. (2009 ▶); Zeng et al. (2010 ▶). For a related structure, see: Li et al. (2010 ▶). For ring conformations, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C18H22N4O2S

M = 358.46

Monoclinic,

a = 9.4128 (3) Å

b = 10.5636 (5) Å

c = 19.2052 (6) Å

β = 102.347 (1)°

V = 1865.46 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.19 mm−1

T = 298 K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.955, T max = 0.962

12093 measured reflections

3857 independent reflections

3014 reflections with I > 2σ(I)

R int = 0.076

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.139

S = 1.03

3857 reflections

236 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.34 e Å−3

Δρmin = −0.27 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; 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 datablock(s) global, I. DOI: 10.1107/S1600536812019952/hb6711sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812019952/hb6711Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812019952/hb6711Isup3.cml

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

C18H22N4O2S	F(000) = 760.0
Mr = 358.46	Dx = 1.288 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4329 reflections
a = 9.4128 (3) Å	θ = 2.2–27.7°
b = 10.5636 (5) Å	µ = 0.19 mm−1
c = 19.2052 (6) Å	T = 298 K
β = 102.347 (1)°	Block, colorless
V = 1865.46 (12) Å3	0.30 × 0.20 × 0.20 mm
Z = 4

Bruker SMART CCD diffractometer	3857 independent reflections
Radiation source: fine-focus sealed tube	3014 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.076
φ and ω scans	θmax = 26.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
Tmin = 0.955, Tmax = 0.962	k = −13→10
12093 measured reflections	l = −24→24

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.139	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0772P)2 + 0.1069P] where P = (Fo2 + 2Fc2)/3
3857 reflections	(Δ/σ)max = 0.025
236 parameters	Δρmax = 0.34 e Å−3
2 restraints	Δρmin = −0.27 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
C1	0.09011 (18)	0.72990 (17)	0.84262 (9)	0.0364 (4)
C2	0.0719 (2)	0.67844 (18)	0.77505 (10)	0.0462 (5)
H2	0.0294	0.5991	0.7656	0.055*
C3	0.1170 (3)	0.7450 (2)	0.72128 (10)	0.0570 (6)
H3	0.1042	0.7107	0.6758	0.068*
C4	0.1809 (3)	0.8623 (2)	0.73568 (11)	0.0558 (6)
H4	0.2120	0.9067	0.6998	0.067*
C5	0.1991 (2)	0.91431 (19)	0.80297 (10)	0.0494 (5)
H5	0.2422	0.9935	0.8120	0.059*
C6	0.1535 (2)	0.84940 (17)	0.85729 (9)	0.0380 (4)
C7	0.17531 (19)	0.83292 (16)	0.97816 (9)	0.0348 (4)
C8	0.04635 (19)	0.66650 (16)	0.90571 (9)	0.0345 (4)
H8	−0.0437	0.7061	0.9126	0.041*
C9	0.2171 (2)	1.00033 (18)	1.06939 (10)	0.0466 (5)
H9	0.1470	1.0559	1.0387	0.056*
C10	0.1933 (3)	1.0103 (2)	1.14433 (12)	0.0612 (6)
H10A	0.0963	0.9833	1.1453	0.092*
H10B	0.2063	1.0965	1.1601	0.092*
H10C	0.2621	0.9573	1.1753	0.092*
C11	0.3679 (3)	1.0396 (2)	1.06328 (15)	0.0795 (8)
H11A	0.4385	0.9897	1.0953	0.119*
H11B	0.3823	1.1275	1.0754	0.119*
H11C	0.3791	1.0265	1.0153	0.119*
C12	0.28831 (19)	0.62791 (16)	0.97962 (9)	0.0343 (4)
C13	0.13802 (19)	0.44969 (16)	0.92654 (9)	0.0363 (4)
C14	0.02360 (19)	0.52521 (16)	0.90196 (9)	0.0355 (4)
C15	0.1435 (2)	0.30767 (17)	0.92606 (12)	0.0502 (5)
H15A	0.1103	0.2753	0.9665	0.075*
H15B	0.2417	0.2804	0.9284	0.075*
H15C	0.0821	0.2765	0.8830	0.075*
C16	−0.1233 (2)	0.47530 (18)	0.87161 (9)	0.0404 (4)
C17	−0.3692 (2)	0.5353 (2)	0.82596 (12)	0.0552 (5)
H17A	−0.4100	0.4905	0.8612	0.066*
H17B	−0.3745	0.4806	0.7849	0.066*
C18	−0.4504 (3)	0.6539 (3)	0.8048 (2)	0.0979 (11)
H18A	−0.4431	0.7077	0.8457	0.147*
H18B	−0.5508	0.6345	0.7856	0.147*
H18C	−0.4101	0.6966	0.7693	0.147*
S1	0.44958 (5)	0.68615 (5)	1.01900 (3)	0.04898 (19)
N1	0.16807 (17)	0.90727 (14)	0.92474 (8)	0.0399 (4)
N2	0.18611 (17)	0.86974 (14)	1.04561 (8)	0.0387 (4)
H2A	0.191 (2)	0.8115 (14)	1.0774 (8)	0.046*
N3	0.16359 (15)	0.69732 (13)	0.96840 (7)	0.0326 (3)
N4	0.27056 (16)	0.50620 (14)	0.95704 (8)	0.0393 (4)
H4A	0.3503 (15)	0.4619 (16)	0.9646 (10)	0.047*
O1	−0.21898 (14)	0.57011 (13)	0.85569 (8)	0.0525 (4)
O2	−0.15658 (16)	0.36556 (14)	0.86187 (8)	0.0569 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0333 (9)	0.0385 (10)	0.0363 (9)	0.0059 (8)	0.0045 (7)	0.0066 (7)
C2	0.0516 (12)	0.0455 (11)	0.0392 (10)	0.0030 (9)	0.0045 (9)	0.0016 (8)
C3	0.0744 (15)	0.0612 (14)	0.0352 (10)	0.0142 (12)	0.0113 (10)	0.0055 (9)
C4	0.0695 (15)	0.0559 (13)	0.0460 (11)	0.0109 (11)	0.0215 (10)	0.0180 (10)
C5	0.0567 (13)	0.0425 (11)	0.0509 (11)	0.0035 (9)	0.0163 (10)	0.0131 (9)
C6	0.0387 (10)	0.0348 (10)	0.0401 (9)	0.0068 (8)	0.0077 (8)	0.0051 (7)
C7	0.0306 (9)	0.0329 (9)	0.0409 (9)	0.0019 (7)	0.0077 (7)	−0.0004 (7)
C8	0.0298 (8)	0.0366 (10)	0.0357 (8)	0.0006 (7)	0.0041 (7)	0.0004 (7)
C9	0.0554 (12)	0.0361 (10)	0.0481 (11)	0.0040 (9)	0.0107 (9)	−0.0051 (8)
C10	0.0690 (15)	0.0603 (14)	0.0544 (12)	0.0072 (12)	0.0140 (11)	−0.0168 (10)
C11	0.0865 (19)	0.0674 (17)	0.0933 (19)	−0.0312 (14)	0.0387 (16)	−0.0277 (14)
C12	0.0369 (9)	0.0324 (9)	0.0338 (8)	0.0020 (7)	0.0077 (7)	0.0034 (7)
C13	0.0379 (10)	0.0346 (9)	0.0379 (9)	−0.0025 (7)	0.0113 (7)	0.0015 (7)
C14	0.0362 (9)	0.0358 (10)	0.0348 (9)	−0.0028 (7)	0.0085 (7)	0.0006 (7)
C15	0.0483 (12)	0.0375 (11)	0.0662 (13)	−0.0022 (9)	0.0150 (10)	0.0009 (9)
C16	0.0414 (10)	0.0440 (11)	0.0356 (9)	−0.0047 (9)	0.0074 (8)	0.0039 (8)
C17	0.0373 (11)	0.0642 (14)	0.0587 (12)	−0.0093 (10)	−0.0021 (9)	−0.0010 (10)
C18	0.0541 (16)	0.0719 (18)	0.148 (3)	0.0067 (13)	−0.0231 (17)	−0.0301 (18)
S1	0.0332 (3)	0.0401 (3)	0.0684 (4)	0.00183 (19)	−0.0007 (2)	−0.0082 (2)
N1	0.0450 (9)	0.0325 (8)	0.0420 (8)	0.0024 (7)	0.0088 (7)	0.0039 (6)
N2	0.0451 (9)	0.0327 (8)	0.0389 (8)	0.0017 (7)	0.0104 (7)	−0.0004 (6)
N3	0.0310 (7)	0.0323 (8)	0.0335 (7)	0.0012 (6)	0.0043 (6)	0.0010 (6)
N4	0.0338 (8)	0.0320 (8)	0.0507 (9)	0.0033 (6)	0.0057 (7)	0.0006 (7)
O1	0.0345 (7)	0.0504 (9)	0.0675 (9)	−0.0043 (6)	−0.0002 (6)	−0.0017 (7)
O2	0.0522 (9)	0.0447 (9)	0.0673 (9)	−0.0126 (7)	−0.0016 (7)	0.0034 (7)

C1—C2	1.384 (2)	C11—H11A	0.9600
C1—C6	1.399 (3)	C11—H11B	0.9600
C1—C8	1.516 (2)	C11—H11C	0.9600
C2—C3	1.389 (3)	C12—N4	1.356 (2)
C2—H2	0.9300	C12—N3	1.362 (2)
C3—C4	1.380 (3)	C12—S1	1.6625 (18)
C3—H3	0.9300	C13—C14	1.342 (2)
C4—C5	1.381 (3)	C13—N4	1.394 (2)
C4—H4	0.9300	C13—C15	1.501 (2)
C5—C6	1.390 (3)	C14—C16	1.478 (2)
C5—H5	0.9300	C15—H15A	0.9600
C6—N1	1.412 (2)	C15—H15B	0.9600
C7—N1	1.282 (2)	C15—H15C	0.9600
C7—N2	1.335 (2)	C16—O2	1.205 (2)
C7—N3	1.446 (2)	C16—O1	1.338 (2)
C8—N3	1.485 (2)	C17—O1	1.454 (2)
C8—C14	1.507 (2)	C17—C18	1.479 (3)
C8—H8	0.9800	C17—H17A	0.9700
C9—N2	1.463 (2)	C17—H17B	0.9700
C9—C10	1.507 (3)	C18—H18A	0.9600
C9—C11	1.507 (3)	C18—H18B	0.9600
C9—H9	0.9800	C18—H18C	0.9600
C10—H10A	0.9600	N2—H2A	0.861 (9)
C10—H10B	0.9600	N4—H4A	0.870 (9)
C10—H10C	0.9600
C2—C1—C6	120.35 (16)	H11A—C11—H11C	109.5
C2—C1—C8	125.15 (16)	H11B—C11—H11C	109.5
C6—C1—C8	114.50 (15)	N4—C12—N3	114.64 (15)
C1—C2—C3	120.16 (19)	N4—C12—S1	122.31 (13)
C1—C2—H2	119.9	N3—C12—S1	123.04 (13)
C3—C2—H2	119.9	C14—C13—N4	118.16 (16)
C4—C3—C2	119.69 (19)	C14—C13—C15	128.17 (17)
C4—C3—H3	120.2	N4—C13—C15	113.67 (16)
C2—C3—H3	120.2	C13—C14—C16	122.63 (17)
C3—C4—C5	120.42 (19)	C13—C14—C8	118.46 (16)
C3—C4—H4	119.8	C16—C14—C8	118.91 (15)
C5—C4—H4	119.8	C13—C15—H15A	109.5
C4—C5—C6	120.66 (19)	C13—C15—H15B	109.5
C4—C5—H5	119.7	H15A—C15—H15B	109.5
C6—C5—H5	119.7	C13—C15—H15C	109.5
C5—C6—C1	118.72 (17)	H15A—C15—H15C	109.5
C5—C6—N1	119.32 (17)	H15B—C15—H15C	109.5
C1—C6—N1	121.92 (15)	O2—C16—O1	122.99 (17)
N1—C7—N2	125.29 (16)	O2—C16—C14	126.50 (18)
N1—C7—N3	120.91 (15)	O1—C16—C14	110.52 (16)
N2—C7—N3	113.72 (15)	O1—C17—C18	107.19 (18)
N3—C8—C14	109.22 (13)	O1—C17—H17A	110.3
N3—C8—C1	105.62 (13)	C18—C17—H17A	110.3
C14—C8—C1	117.33 (14)	O1—C17—H17B	110.3
N3—C8—H8	108.1	C18—C17—H17B	110.3
C14—C8—H8	108.1	H17A—C17—H17B	108.5
C1—C8—H8	108.1	C17—C18—H18A	109.5
N2—C9—C10	107.66 (17)	C17—C18—H18B	109.5
N2—C9—C11	111.32 (17)	H18A—C18—H18B	109.5
C10—C9—C11	112.96 (19)	C17—C18—H18C	109.5
N2—C9—H9	108.3	H18A—C18—H18C	109.5
C10—C9—H9	108.3	H18B—C18—H18C	109.5
C11—C9—H9	108.3	C7—N1—C6	116.54 (15)
C9—C10—H10A	109.5	C7—N2—C9	123.11 (15)
C9—C10—H10B	109.5	C7—N2—H2A	117.5 (13)
H10A—C10—H10B	109.5	C9—N2—H2A	118.4 (13)
C9—C10—H10C	109.5	C12—N3—C7	118.27 (14)
H10A—C10—H10C	109.5	C12—N3—C8	118.45 (14)
H10B—C10—H10C	109.5	C7—N3—C8	110.19 (13)
C9—C11—H11A	109.5	C12—N4—C13	125.35 (15)
C9—C11—H11B	109.5	C12—N4—H4A	114.4 (14)
H11A—C11—H11B	109.5	C13—N4—H4A	120.2 (14)
C9—C11—H11C	109.5	C16—O1—C17	116.80 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2i	0.86 (1)	2.26 (1)	3.102 (2)	165 (2)
N4—H4A···S1ii	0.87 (1)	2.42 (1)	3.2804 (15)	172 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O2i	0.86 (1)	2.26 (1)	3.102 (2)	165 (2)
N4—H4A⋯S1ii	0.87 (1)	2.42 (1)	3.2804 (15)	172 (2)

Symmetry codes: (i) ; (ii) .