Ethyl 2-isopropyl­amino-5-methyl-4-oxo-3-phenyl-3,4-dihydro­thieno[2,3-d]pyrimidine-6-carboxyl­ate

Zheng, A.-H.; Huang, L.-Y.; Chen, E.; Luo, H.

doi:10.1107/S1600536809045449

organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page o2993

doi:10.1107/S1600536809045449

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Ethyl 2-isopropylamino-5-methyl-4-oxo-3-phenyl-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylate

Ai-Hua Zheng,^a Liang-Yong Huang,^b ^* E. Chen ^c and Hong Luo ^d

^aInstitute of Medicinal Chemistry, Yunyang Medical College, Shiyan 442000, People's Republic of China, ^bDepartment of Pharmacy, Taihe Hospital of Yunyang Medical College, Shiyan 442000, People's Republic of China, ^cDepartment of Pharmacy, Renmin Hospital of Yunyang Medical College, Shiyan 442000, People's Republic of China, and ^dDepartment of Medicinal Physics, Yunyang Medical College, Shiyan 442000, People's Republic of China
^*Correspondence e-mail: lyhuang6686@yahoo.com.cn

(Received 25 October 2009; accepted 29 October 2009; online 4 November 2009)

The title compound, C₁₉H₂₁N₃O₃S, was synthesized via an aza-Wittig reaction of a functionalized iminophosphorane with phenyl isocyanate under mild conditions. In the molecule, the fused thienopyrimidine ring system makes a dihedral angle of 66.30 (11)° with the phenyl ring. An intramolecular C—H⋯O hydrogen bond occurs. The terminal –OCH₂CH₃ group is disordered over two sites with refined occupancies of 0.537 (13) and 0.463 (13). The crystal packing is stabilized by intermolecular C—H⋯O and N—H⋯O hydrogen bonds.

Related literature

For the biological and pharmaceutical activity of pyrimidinone derivatives, see: Modica et al. (2004 ); Panico et al. (2001 ). For related structures, see: Zheng et al. (2007 ); Hu et al. (2007 ); Xu (2008 ); Xu et al. (2006 ).

Experimental

Crystal data

C₁₉H₂₁N₃O₃S
M_r = 371.45
Orthorhombic, P 2₁ 2₁ 2₁
a = 8.5995 (14) Å
b = 13.673 (2) Å
c = 15.912 (3) Å
V = 1871.0 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 298 K
0.30 × 0.20 × 0.10 mm

Data collection

Bruker SMART 4K CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.943, T_max = 0.981
12706 measured reflections
4636 independent reflections
4149 reflections with I > 2σ(I)
R_int = 0.061

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.123
S = 1.10
4636 reflections
271 parameters
6 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.22 e Å⁻³
Absolute structure: Flack (1983 ), 1984 Friedel pairs
Flack parameter: 0.09 (8)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16A⋯O2	0.96	2.33	3.015 (3)	128
C6—H6⋯O2ⁱ	0.93	2.58	3.479 (3)	164
N3—H3A⋯O1ⁱⁱ	0.77 (3)	2.28 (3)	2.949 (2)	145 (2)
Symmetry codes: (i) $[-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ .

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; 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 I, global. DOI: 10.1107/S1600536809045449/bt5115sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809045449/bt5115Isup2.hkl

checkCIF report

Comment top

Derivatives of pyrimidinone are attracting increasing attention in the synthetic chemistry community because of the important role played by such systems in many natural products, also in antibiotics and drugs (Modica et al., 2004; Panico et al., 2001). Recently, we have been interested in the synthesis of new thieno[3,2-d]pyrimidone derivatives. Some related X-ray crystal structure reports for pyrimidinone derivatives have been published (Zheng et al., 2007; Hu et al. 2007; Xu et al., 2006, 2008). Here, the structure of the title compound, which may be used as a new precursor for obtaining bioactive molecules, is reported (Fig. 1). In the molecule, the bond lengths and angles are unexceptional. The thienopyrimidinone rings are closer to coplanarity with maximum deviations 0.074 (2)Å for N3. The phenyl ring is twisted with respect to the pyrimidinone ring, with a dihedral angle of 66.30 (11)°. C18, C19 and attached hydrogen and O3 atoms are disordered over two sites, with refined occupancies of 0.537 (13) and 0.463 (13). Intramolecular C—H···O and intermolecular C—H···O, N—H···O hydrogen bonds interactions are present, which stabilize the conformation of the molecule and the crystal structure (Table 1).

Related literature top

For the biological and pharmaceutical activity of pyrimidinone derivatives, see: Modica et al. (2004); Panico et al. (2001). For related structures, see: Zheng et al. (2007); Hu et al. (2007); Xu et al. (2006, 2008).

Experimental top

To a solution of diethyl 5-((phenylimino)methyleneamino)- 3-methylthiophene-2,4-dicarboxylate(3 mmol) in anhydrous dichloromethane (15 ml) was added iso-propan-1-amine (3 mmol). After stirring the reaction mixture for 1 h, the solvent was removed and anhydrous ethanol (10 ml) with several drops of EtONa in EtOH was added. The mixture was stirred for 5 h at room temperature. The solution was concentrated under reduced pressure and the residue was recrystallized from ethanol to give the title compound in a yield of 85%. Crystals suitable for single-crystal X-ray diffraction were obtained by recrystallization from a mixed solvent of ethanol and dichloromethane (1:1 v/v) at room temperature.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (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. The molecular structure of the title compound, showing the atom-labeling scheme.

Ethyl 2-isopropylamino-5-methyl-4-oxo-3-phenyl-3,4- dihydrothieno[2,3-d]pyrimidine-6-carboxylate top

Crystal data top

C₁₉H₂₁N₃O₃S	F(000) = 784
M_r = 371.45	D_x = 1.319 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4510 reflections
a = 8.5995 (14) Å	θ = 2.6–26.5°
b = 13.673 (2) Å	µ = 0.20 mm⁻¹
c = 15.912 (3) Å	T = 298 K
V = 1871.0 (5) Å³	Block, colorless
Z = 4	0.30 × 0.20 × 0.10 mm

Data collection top

Bruker SMART 4K CCD area-detector diffractometer	4636 independent reflections
Radiation source: fine-focus sealed tube	4149 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.061
ϕ and ω scans	θ_max = 28.3°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −7→11
T_min = 0.943, T_max = 0.981	k = −18→17
12706 measured reflections	l = −21→18

Refinement top

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)] = 0.050	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.123	w = 1/[σ²(F_o²) + (0.0601P)²] where P = (F_o² + 2F_c²)/3
S = 1.10	(Δ/σ)_max < 0.001
4636 reflections	Δρ_max = 0.33 e Å⁻³
271 parameters	Δρ_min = −0.22 e Å⁻³
6 restraints	Absolute structure: Flack (1983), 1984 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.09 (8)

Crystal data top

C₁₉H₂₁N₃O₃S	V = 1871.0 (5) Å³
M_r = 371.45	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 8.5995 (14) Å	µ = 0.20 mm⁻¹
b = 13.673 (2) Å	T = 298 K
c = 15.912 (3) Å	0.30 × 0.20 × 0.10 mm

Data collection top

Bruker SMART 4K CCD area-detector diffractometer	4636 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	4149 reflections with I > 2σ(I)
T_min = 0.943, T_max = 0.981	R_int = 0.061
12706 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.123	Δρ_max = 0.33 e Å⁻³
S = 1.10	Δρ_min = −0.22 e Å⁻³
4636 reflections	Absolute structure: Flack (1983), 1984 Friedel pairs
271 parameters	Absolute structure parameter: 0.09 (8)
6 restraints

Special details top

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.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	0.2137 (2)	0.27871 (14)	0.47156 (12)	0.0406 (4)
C2	0.2947 (3)	0.21627 (15)	0.41948 (14)	0.0488 (5)
H2	0.3578	0.1675	0.4417	0.059*
C3	0.2800 (3)	0.22783 (18)	0.33286 (15)	0.0606 (6)
H3	0.3351	0.1869	0.2969	0.073*
C4	0.1855 (4)	0.2987 (2)	0.30019 (16)	0.0694 (8)
H4	0.1765	0.3056	0.2423	0.083*
C5	0.1040 (4)	0.3595 (2)	0.35261 (17)	0.0716 (8)
H5	0.0385	0.4070	0.3303	0.086*
C6	0.1196 (3)	0.35009 (17)	0.43916 (15)	0.0552 (6)
H6	0.0663	0.3921	0.4749	0.066*
C7	0.2851 (2)	0.34531 (13)	0.61047 (13)	0.0395 (4)
C8	0.2038 (2)	0.27158 (14)	0.72863 (12)	0.0408 (4)
C9	0.1490 (2)	0.18802 (14)	0.68884 (12)	0.0376 (4)
C10	0.1562 (2)	0.18457 (13)	0.59891 (13)	0.0391 (4)
C11	0.4070 (3)	0.50790 (14)	0.60896 (14)	0.0464 (5)
H11	0.3291	0.5270	0.6508	0.056*
C12	0.4122 (4)	0.5855 (2)	0.5416 (2)	0.0834 (10)
H12A	0.4823	0.5656	0.4979	0.125*
H12B	0.4476	0.6460	0.5655	0.125*
H12C	0.3101	0.5944	0.5185	0.125*
C13	0.5612 (3)	0.4960 (2)	0.6528 (2)	0.0693 (7)
H13A	0.5529	0.4459	0.6948	0.104*
H13B	0.5899	0.5566	0.6790	0.104*
H13C	0.6392	0.4779	0.6125	0.104*
C14	0.0844 (2)	0.11758 (14)	0.74560 (13)	0.0400 (4)
C15	0.0934 (2)	0.14955 (14)	0.82673 (14)	0.0446 (5)
C16	0.0151 (3)	0.02200 (17)	0.71855 (17)	0.0597 (6)
H16A	−0.0409	−0.0065	0.7647	0.089*
H16B	0.0966	−0.0216	0.7012	0.089*
H16C	−0.0547	0.0328	0.6724	0.089*
C17	0.0542 (3)	0.09639 (19)	0.90376 (15)	0.0544 (6)
C18'	0.0196 (9)	0.1295 (7)	1.0546 (4)	0.065 (2)	0.463 (13)
H18C	−0.0535	0.0755	1.0519	0.078*	0.463 (13)
H18D	−0.0262	0.1809	1.0885	0.078*	0.463 (13)
C19'	0.1698 (11)	0.0955 (10)	1.0941 (7)	0.099 (4)	0.463 (13)
H19D	0.2073	0.0388	1.0648	0.148*	0.463 (13)
H19E	0.1519	0.0792	1.1520	0.148*	0.463 (13)
H19F	0.2457	0.1468	1.0907	0.148*	0.463 (13)
O3'	0.0508 (11)	0.1657 (6)	0.9710 (4)	0.0593 (17)	0.463 (13)
C18	0.0891 (12)	0.0864 (5)	1.0496 (3)	0.070 (2)	0.537 (13)
H18A	0.1427	0.0240	1.0484	0.084*	0.537 (13)
H18B	−0.0205	0.0748	1.0601	0.084*	0.537 (13)
C19	0.1567 (16)	0.1515 (7)	1.1163 (5)	0.106 (3)	0.537 (13)
H19A	0.2569	0.1746	1.0984	0.160*	0.537 (13)
H19B	0.1676	0.1154	1.1676	0.160*	0.537 (13)
H19C	0.0889	0.2063	1.1253	0.160*	0.537 (13)
O3	0.1105 (10)	0.1383 (5)	0.9708 (3)	0.0599 (15)	0.537 (13)
N1	0.22489 (19)	0.26857 (11)	0.56226 (10)	0.0390 (4)
N2	0.2725 (2)	0.34924 (12)	0.69284 (11)	0.0414 (4)
N3	0.3553 (2)	0.41720 (12)	0.56877 (12)	0.0464 (4)
H3A	0.387 (3)	0.4055 (18)	0.5245 (18)	0.056*
O1	0.1063 (2)	0.11958 (11)	0.55348 (10)	0.0530 (4)
O2	0.0060 (2)	0.01385 (13)	0.90784 (12)	0.0684 (5)
S1	0.17644 (7)	0.26585 (4)	0.83568 (3)	0.05191 (16)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0506 (11)	0.0394 (10)	0.0320 (9)	−0.0100 (9)	0.0019 (8)	−0.0027 (8)
C2	0.0563 (12)	0.0467 (10)	0.0435 (11)	−0.0021 (9)	−0.0007 (9)	−0.0103 (9)
C3	0.0789 (16)	0.0605 (13)	0.0425 (12)	−0.0130 (12)	0.0112 (12)	−0.0177 (12)
C4	0.102 (2)	0.0714 (17)	0.0345 (12)	−0.0149 (17)	−0.0017 (13)	0.0018 (11)
C5	0.099 (2)	0.0705 (16)	0.0456 (15)	0.0111 (15)	−0.0045 (14)	0.0150 (13)
C6	0.0710 (15)	0.0511 (12)	0.0434 (13)	0.0092 (11)	0.0073 (11)	0.0047 (10)
C7	0.0475 (11)	0.0334 (9)	0.0375 (10)	−0.0033 (8)	0.0027 (8)	−0.0061 (7)
C8	0.0475 (11)	0.0422 (10)	0.0327 (9)	−0.0002 (9)	0.0015 (8)	−0.0026 (8)
C9	0.0428 (10)	0.0340 (8)	0.0359 (9)	−0.0008 (8)	−0.0028 (8)	0.0014 (7)
C10	0.0460 (10)	0.0325 (8)	0.0389 (10)	0.0009 (8)	−0.0033 (8)	−0.0008 (7)
C11	0.0578 (13)	0.0343 (9)	0.0472 (12)	−0.0073 (9)	0.0111 (10)	−0.0077 (8)
C12	0.122 (3)	0.0458 (13)	0.082 (2)	−0.0179 (16)	0.0038 (19)	0.0125 (14)
C13	0.0615 (15)	0.0708 (16)	0.0756 (19)	−0.0120 (13)	−0.0005 (14)	−0.0171 (15)
C14	0.0424 (10)	0.0358 (9)	0.0418 (11)	0.0007 (8)	0.0007 (8)	0.0052 (8)
C15	0.0475 (11)	0.0414 (10)	0.0449 (12)	−0.0033 (8)	−0.0007 (9)	0.0060 (9)
C16	0.0805 (17)	0.0412 (12)	0.0573 (15)	−0.0124 (11)	0.0060 (13)	0.0022 (11)
C17	0.0591 (14)	0.0637 (14)	0.0403 (12)	−0.0082 (11)	−0.0004 (10)	0.0081 (11)
C18'	0.082 (5)	0.059 (4)	0.053 (4)	0.003 (3)	0.020 (3)	0.003 (3)
C19'	0.099 (6)	0.128 (10)	0.070 (7)	0.009 (7)	−0.001 (5)	0.028 (7)
O3'	0.083 (5)	0.055 (4)	0.040 (2)	−0.004 (3)	0.006 (3)	0.007 (2)
C18	0.107 (6)	0.071 (4)	0.032 (3)	−0.005 (4)	−0.004 (3)	0.013 (3)
C19	0.193 (10)	0.073 (5)	0.054 (4)	−0.001 (5)	−0.024 (5)	0.003 (3)
O3	0.090 (4)	0.050 (3)	0.0398 (19)	0.000 (2)	−0.002 (2)	0.0111 (18)
N1	0.0515 (9)	0.0339 (7)	0.0315 (8)	−0.0024 (7)	0.0007 (7)	−0.0029 (7)
N2	0.0549 (10)	0.0348 (8)	0.0345 (9)	−0.0057 (7)	0.0030 (7)	−0.0040 (7)
N3	0.0623 (11)	0.0403 (8)	0.0365 (9)	−0.0117 (8)	0.0130 (8)	−0.0084 (7)
O1	0.0762 (11)	0.0409 (7)	0.0420 (9)	−0.0149 (7)	−0.0053 (8)	−0.0033 (6)
O2	0.0874 (13)	0.0600 (10)	0.0578 (11)	−0.0188 (10)	0.0060 (10)	0.0144 (9)
S1	0.0734 (4)	0.0499 (3)	0.0324 (2)	−0.0140 (3)	0.0024 (2)	−0.0019 (2)

Geometric parameters (Å, º) top

C1—C6	1.369 (3)	C13—H13A	0.9600
C1—C2	1.379 (3)	C13—H13B	0.9600
C1—N1	1.453 (2)	C13—H13C	0.9600
C2—C3	1.393 (3)	C14—C15	1.365 (3)
C2—H2	0.9300	C14—C16	1.499 (3)
C3—C4	1.367 (4)	C15—C17	1.464 (3)
C3—H3	0.9300	C15—S1	1.749 (2)
C4—C5	1.371 (4)	C16—H16A	0.9600
C4—H4	0.9300	C16—H16B	0.9600
C5—C6	1.390 (3)	C16—H16C	0.9600
C5—H5	0.9300	C17—O2	1.204 (3)
C6—H6	0.9300	C17—O3	1.303 (7)
C7—N2	1.316 (3)	C17—O3'	1.429 (8)
C7—N3	1.331 (3)	C18'—O3'	1.445 (7)
C7—N1	1.399 (2)	C18'—C19'	1.510 (8)
C8—N2	1.342 (2)	C18'—H18C	0.9700
C8—C9	1.389 (3)	C18'—H18D	0.9700
C8—S1	1.721 (2)	C19'—H19D	0.9600
C9—C14	1.433 (3)	C19'—H19E	0.9600
C9—C10	1.433 (3)	C19'—H19F	0.9600
C10—O1	1.223 (2)	C18—O3	1.453 (6)
C10—N1	1.417 (2)	C18—C19	1.502 (7)
C11—N3	1.464 (3)	C18—H18A	0.9700
C11—C13	1.508 (4)	C18—H18B	0.9700
C11—C12	1.509 (4)	C19—H19A	0.9600
C11—H11	0.9800	C19—H19B	0.9600
C12—H12A	0.9600	C19—H19C	0.9600
C12—H12B	0.9600	N3—H3A	0.77 (3)
C12—H12C	0.9600

C6—C1—C2	120.9 (2)	H13B—C13—H13C	109.5
C6—C1—N1	118.77 (19)	C15—C14—C9	111.03 (18)
C2—C1—N1	120.30 (19)	C15—C14—C16	125.0 (2)
C1—C2—C3	118.6 (2)	C9—C14—C16	123.99 (19)
C1—C2—H2	120.7	C14—C15—C17	128.3 (2)
C3—C2—H2	120.7	C14—C15—S1	113.04 (16)
C4—C3—C2	120.7 (2)	C17—C15—S1	118.50 (17)
C4—C3—H3	119.7	C14—C16—H16A	109.5
C2—C3—H3	119.7	C14—C16—H16B	109.5
C3—C4—C5	120.2 (2)	H16A—C16—H16B	109.5
C3—C4—H4	119.9	C14—C16—H16C	109.5
C5—C4—H4	119.9	H16A—C16—H16C	109.5
C4—C5—C6	119.8 (2)	H16B—C16—H16C	109.5
C4—C5—H5	120.1	O2—C17—O3	119.7 (3)
C6—C5—H5	120.1	O2—C17—O3'	125.0 (3)
C1—C6—C5	119.8 (2)	O3—C17—O3'	26.4 (3)
C1—C6—H6	120.1	O2—C17—C15	126.1 (2)
C5—C6—H6	120.1	O3—C17—C15	112.4 (3)
N2—C7—N3	120.23 (18)	O3'—C17—C15	107.6 (3)
N2—C7—N1	123.12 (18)	O3'—C18'—C19'	109.3 (6)
N3—C7—N1	116.64 (17)	O3'—C18'—H18C	109.8
N2—C8—C9	127.35 (18)	C19'—C18'—H18C	109.8
N2—C8—S1	121.07 (14)	O3'—C18'—H18D	109.8
C9—C8—S1	111.57 (14)	C19'—C18'—H18D	109.8
C8—C9—C14	113.40 (18)	H18C—C18'—H18D	108.3
C8—C9—C10	117.90 (18)	C17—O3'—C18'	117.8 (5)
C14—C9—C10	128.62 (19)	O3—C18—C19	105.8 (5)
O1—C10—N1	119.46 (18)	O3—C18—H18A	110.6
O1—C10—C9	126.79 (19)	C19—C18—H18A	110.6
N1—C10—C9	113.72 (17)	O3—C18—H18B	110.6
N3—C11—C13	112.19 (19)	C19—C18—H18B	110.6
N3—C11—C12	107.1 (2)	H18A—C18—H18B	108.7
C13—C11—C12	112.2 (2)	C18—C19—H19A	109.5
N3—C11—H11	108.4	C18—C19—H19B	109.5
C13—C11—H11	108.4	H19A—C19—H19B	109.5
C12—C11—H11	108.4	C18—C19—H19C	109.5
C11—C12—H12A	109.5	H19A—C19—H19C	109.5
C11—C12—H12B	109.5	H19B—C19—H19C	109.5
H12A—C12—H12B	109.5	C17—O3—C18	116.4 (5)
C11—C12—H12C	109.5	C7—N1—C10	122.44 (16)
H12A—C12—H12C	109.5	C7—N1—C1	119.84 (16)
H12B—C12—H12C	109.5	C10—N1—C1	117.29 (15)
C11—C13—H13A	109.5	C7—N2—C8	115.24 (17)
C11—C13—H13B	109.5	C7—N3—C11	123.06 (18)
H13A—C13—H13B	109.5	C7—N3—H3A	117.6 (19)
C11—C13—H13C	109.5	C11—N3—H3A	117.7 (19)
H13A—C13—H13C	109.5	C8—S1—C15	90.95 (10)

C6—C1—C2—C3	0.6 (3)	O3—C17—O3'—C18'	−72.8 (10)
N1—C1—C2—C3	179.51 (18)	C15—C17—O3'—C18'	−177.9 (5)
C1—C2—C3—C4	−1.0 (4)	C19'—C18'—O3'—C17	85.6 (13)
C2—C3—C4—C5	0.1 (4)	O2—C17—O3—C18	−9.1 (7)
C3—C4—C5—C6	1.0 (5)	O3'—C17—O3—C18	100.6 (13)
C2—C1—C6—C5	0.5 (4)	C15—C17—O3—C18	−174.9 (5)
N1—C1—C6—C5	−178.4 (2)	C19—C18—O3—C17	−177.4 (12)
C4—C5—C6—C1	−1.4 (4)	N2—C7—N1—C10	−5.2 (3)
N2—C8—C9—C14	178.76 (19)	N3—C7—N1—C10	175.90 (18)
S1—C8—C9—C14	−0.3 (2)	N2—C7—N1—C1	167.00 (19)
N2—C8—C9—C10	−4.3 (3)	N3—C7—N1—C1	−11.9 (3)
S1—C8—C9—C10	176.67 (15)	O1—C10—N1—C7	−179.60 (19)
C8—C9—C10—O1	−176.0 (2)	C9—C10—N1—C7	2.4 (3)
C14—C9—C10—O1	0.5 (4)	O1—C10—N1—C1	8.0 (3)
C8—C9—C10—N1	1.9 (3)	C9—C10—N1—C1	−170.04 (17)
C14—C9—C10—N1	178.34 (18)	C6—C1—N1—C7	−62.7 (3)
C8—C9—C14—C15	−0.6 (3)	C2—C1—N1—C7	118.4 (2)
C10—C9—C14—C15	−177.1 (2)	C6—C1—N1—C10	109.9 (2)
C8—C9—C14—C16	179.0 (2)	C2—C1—N1—C10	−69.0 (3)
C10—C9—C14—C16	2.4 (4)	N3—C7—N2—C8	−178.13 (19)
C9—C14—C15—C17	−173.8 (2)	N1—C7—N2—C8	3.0 (3)
C16—C14—C15—C17	6.7 (4)	C9—C8—N2—C7	1.7 (3)
C9—C14—C15—S1	1.2 (2)	S1—C8—N2—C7	−179.30 (16)
C16—C14—C15—S1	−178.38 (19)	N2—C7—N3—C11	−6.7 (3)
C14—C15—C17—O2	−0.3 (4)	N1—C7—N3—C11	172.24 (19)
S1—C15—C17—O2	−175.0 (2)	C13—C11—N3—C7	81.3 (3)
C14—C15—C17—O3	164.5 (5)	C12—C11—N3—C7	−155.1 (2)
S1—C15—C17—O3	−10.3 (5)	N2—C8—S1—C15	−178.33 (18)
C14—C15—C17—O3'	−167.9 (5)	C9—C8—S1—C15	0.79 (16)
S1—C15—C17—O3'	17.4 (5)	C14—C15—S1—C8	−1.14 (17)
O2—C17—O3'—C18'	14.3 (9)	C17—C15—S1—C8	174.36 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16A···O2	0.96	2.33	3.015 (3)	128
C6—H6···O2ⁱ	0.93	2.58	3.479 (3)	164
N3—H3A···O1ⁱⁱ	0.77 (3)	2.28 (3)	2.949 (2)	145 (2)

Symmetry codes: (i) −x, y+1/2, −z+3/2; (ii) x+1/2, −y+1/2, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₉H₂₁N₃O₃S
M_r	371.45
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	298
a, b, c (Å)	8.5995 (14), 13.673 (2), 15.912 (3)
V (Å³)	1871.0 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Bruker SMART 4K CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.943, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections	12706, 4636, 4149
R_int	0.061
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.123, 1.10
No. of reflections	4636
No. of parameters	271
No. of restraints	6
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.22
Absolute structure	Flack (1983), 1984 Friedel pairs
Absolute structure parameter	0.09 (8)

Computer programs: SMART (Bruker, 2001), SAINT-Plus (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
C16—H16A···O2	0.96	2.33	3.015 (3)	127.7
C6—H6···O2ⁱ	0.93	2.58	3.479 (3)	164.1
N3—H3A···O1ⁱⁱ	0.77 (3)	2.28 (3)	2.949 (2)	145 (2)

Symmetry codes: (i) −x, y+1/2, −z+3/2; (ii) x+1/2, −y+1/2, −z+1.

Acknowledgements

We gratefully acknowledge financial support of this work by the Key Science Research Project of Hubei Provincial Department of Education (No. D20092406).

References

Bruker (2001). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Hu, Y.-G., Chen, Y.-L., Xie, T. & Liu, M.-G. (2007). Acta Cryst. E63, o3474–o3475. Web of Science CSD CrossRef IUCr Journals Google Scholar
Modica, M., Romeo, G., Materia, L., Russo, F., Cagnotto, A., Mennini, T., Falkay, G. & George, F. (2004). Bioorg. Med. Chem. 12, 3891–3901. Web of Science CrossRef PubMed CAS Google Scholar
Panico, A., Cardile, V., Santagati, A. & Gentile, B. (2001). Il Farm. 56, 959–964. Web of Science CrossRef CAS 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
Xu, S.-Z. (2008). Acta Cryst. E64, o222. Web of Science CSD CrossRef IUCr Journals Google Scholar
Xu, S.-Z., Hu, Y.-G., Liu, M.-G. & Ding, M.-W. (2006). Acta Cryst. E62, o3428–o3429. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zheng, A.-H., Long, J.-Y., Zeng, X.-H. & Wang, H.-M. (2007). Acta Cryst. E63, o1142–o1144. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 65| Part 12| December 2009| Page o2993

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

Ethyl 2-iso­propyl­amino-5-methyl-4-oxo-3-phenyl-3,4-di­hydro­thieno[2,3-d]pyrimidine-6-carboxyl­ate

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Experimental

Crystal data

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Supporting information

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organic compounds

Ethyl 2-isopropylamino-5-methyl-4-oxo-3-phenyl-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylate