Ethyl 2-methyl-6-(propan-2-yl­amino)-4-sulfanyl­idene-3H,11H-pyrimido[1,6-c]quinazoline-1-carboxyl­ate

Li, H.-X.; Song, Y.-S.; Qu, Y.; Lu, J.-B.; Wang, H.-M.

doi:10.1107/S1600536812019952

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1821

doi:10.1107/S1600536812019952

Open

access

Ethyl 2-methyl-6-(propan-2-ylamino)-4-sulfanylidene-3H,11H-pyrimido[1,6-c]quinazoline-1-carboxylate

Hong-Xia Li,^a Yu-Su Song,^a Yong-nian Qu,^b Jiang-Bing Lu ^b and Hong-Mei Wang ^b ^*

^aCollege of Science, Naval University of Engineering, Wuhan 430033, People's Republic of China, and ^bInstitute of Medicinal Chemistry, Hubei University of Medicine, Shi Yan 442000, People's Republic of China
^*Correspondence e-mail: meirwang@126.com

(Received 27 March 2012; accepted 3 May 2012; online 19 May 2012)

The title compound, C₁₈H₂₂N₄O₂S, 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 molecules are linked by pairs of N—H⋯S and N—H⋯O hydrogen bonds to generate centrosymmetric R₂²(8) and R₂²(16) loops, respectively. This combination leads to [100] chains of molecules.

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_r = 358.46
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.050
wR(F²) = 0.139
S = 1.03
3857 reflections
236 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.27 e Å⁻³

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) -x, -y+1, -z+2; (ii) -x+1, -y+1, -z+2.

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).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812019952/hb6711sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812019952/hb6711Isup3.cml

checkCIF report

Comment top

In recent years, we have been engaged in the preparation of heterocyclic derivatives using the aza-Wittig reaction (Li et al. 2007, 2008; Huang et al. 2009; Li et al. 2010; Zeng et al., 2010). We present here the crystal structure of the title compound (Fig. 1). The molecule contains a substituted pyrimidine ring fused to a benzene ring and a substituted thioxopyrimidine ring. The centre ring of pyrimidine moiety adopts a distored chair conformation [ϕ = 208.8 (2)° and θ = 68.85 (19)°, Puckering Amplitude = 0.5502 (17)Å], and the substituted thioxopyrimidine ring also show a distorted chair form [ϕ = 214.6 (4)° and θ = 113.9 (3)°, Puckering Amplitude = 0.3827 (17)Å] (Cremer & Pople, 1975). In the crystal, there are N—H···O and N—H···S (Table 1) hydrogen bonds.

Related literature top

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 related literature [on what subject?], see: Cremer & Pople (1975).

Experimental top

To a solution of iminophosphorane prepared according to Li et al. (2010) (0.55 g, 1 mmol) in CH₃CN (10 mL) was added phenylisocyanate (0.12 g, 1 mmol) under nitrogen at room temperature. After stirred for 2 h at room temperature, K₂CO₃ (0.014 g,0.1 mmol) was added and the mixture was stirred for 1 h. The solvent was removed off under reduced pressure and the residue was recrystallized from methylene dichloride and ethanol to give the title compound (I) in yield of 85% (m.p. 490 K). Colourless blocks were obtained from a dichloromethane solution at room temperature.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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).

Figures top

Fig. 1. View of the molecule showing displacement ellipsoids drawn at the 50% probability level.

Ethyl 2-methyl-6-(propan-2-ylamino)-4-sulfanylidene-3H,11H- pyrimido[1,6-c]quinazoline-1-carboxylate top

Crystal data top

C₁₈H₂₂N₄O₂S	F(000) = 760.0
M_r = 358.46	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0772P)² + 0.1069P] where P = (F_o² + 2F_c²)/3
3857 reflections	(Δ/σ)_max = 0.025
236 parameters	Δρ_max = 0.34 e Å⁻³
2 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₁₈H₂₂N₄O₂S	V = 1865.46 (12) Å³
M_r = 358.46	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.4128 (3) Å	µ = 0.19 mm⁻¹
b = 10.5636 (5) Å	T = 298 K
c = 19.2052 (6) Å	0.30 × 0.20 × 0.20 mm
β = 102.347 (1)°

Data collection top

Bruker SMART CCD diffractometer	3857 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3014 reflections with I > 2σ(I)
T_min = 0.955, T_max = 0.962	R_int = 0.076
12093 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	2 restraints
wR(F²) = 0.139	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.34 e Å⁻³
3857 reflections	Δρ_min = −0.27 e Å⁻³
236 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x, −y+1, −z+2; (ii) −x+1, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₈H₂₂N₄O₂S
M_r	358.46
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	9.4128 (3), 10.5636 (5), 19.2052 (6)
β (°)	102.347 (1)
V (Å³)	1865.46 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.19
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.955, 0.962
No. of measured, independent and observed [I > 2σ(I)] reflections	12093, 3857, 3014
R_int	0.076
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.139, 1.03
No. of reflections	3857
No. of parameters	236
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.27

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2ⁱ	0.861 (9)	2.263 (11)	3.102 (2)	164.6 (18)
N4—H4A···S1ⁱⁱ	0.870 (9)	2.417 (10)	3.2804 (15)	172.1 (18)

Symmetry codes: (i) −x, −y+1, −z+2; (ii) −x+1, −y+1, −z+2.

Acknowledgements

The authors gratefully acknowledge financial support of this work by the Foundation of Naval University of Engineering (grant No. HGDQNJJ11007) and Hubei University of Medicine (grant Nos. 2010QDJ02 and 2011XS13).

References

Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Huang, N. Y., Liang, Y. J., Ding, M. W., Fu, L. W. & He, H. W. (2009). Bioorg. Med. Chem. Lett. 19, 831–834. Web of Science CrossRef PubMed CAS Google Scholar
Li, W. J., Liu, S., He, P. & Ding, M. W. (2010). Tetrahedron, 66, 8151–8159. Web of Science CSD CrossRef CAS Google Scholar
Li, H. X., Sun, Y. & Ding, M. W. (2008). Synth. Commun. 38, 4328–4336. Web of Science CSD CrossRef CAS Google Scholar
Li, H. X., Xie, C., Ding, M. W., Liu, Z. M. & Yang, G. F. (2007). Synlett, pp. 2280–2282. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zeng, X. H., Liu, M., Ding, M. W. & He, H. W. (2010). Synth. Commun. 40, 1453–1460. Web of Science CrossRef CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1821

doi:10.1107/S1600536812019952

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Ethyl 2-methyl-6-(propan-2-yl­amino)-4-sulfanyl­­idene-3H,11H-pyrimido[1,6-c]quinazoline-1-carboxyl­ate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Ethyl 2-methyl-6-(propan-2-ylamino)-4-sulfanylidene-3H,11H-pyrimido[1,6-c]quinazoline-1-carboxylate