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

Zheng, A.-H.; Ren, Y.-M.; Xu, J.

doi:10.1107/S1600536809033595

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 9| September 2009| Page o2266

doi:10.1107/S1600536809033595

Open

access

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

Ai-Hua Zheng,^a Yan-Mei Ren ^b and Jing Xu ^a ^*

^aInstitute of Medicinal Chemistry, Yunyang Medical College, Shiyan 442000, People's Republic of China, and ^bClinical Laboratory, Zhushan Center for Disease Control and Prevention, Shiyan 442000, People's Republic of China
^*Correspondence e-mail: jxu6686@yahoo.com.cn

(Received 14 August 2009; accepted 23 August 2009; online 29 August 2009)

The title compound, C₁₉H₂₁N₃O₃S, was synthesized via the aza-Wittig reaction of functionalized iminophosphorane with phenyl isocyanate under mild conditions. In the molecule, the fused thienopyrimidine ring system is essentially planar, with a maximum deviation of 0.072 (2) Å, and makes a dihedral angle of 60.11 (9)° with the phenyl ring. An intramolecular C—H⋯O hydrogen bond is present. The crystal packing is stabilized by intermolecular N—H⋯O and C—H⋯O hydrogen bonds.

Related literature

For the preparation and biological and pharmaceutical activities of pyrimidinone derivatives, see: Modica et al. (2004 ); Panico et al. (2001 ). For the biological activity of thienopyrimidine derivatives, see: Ding et al. (2004 ).

Experimental

Crystal data

C₁₉H₂₁N₃O₃S
M_r = 371.45
Orthorhombic, P 2₁ 2₁ 2₁
a = 8.1682 (2) Å
b = 14.1247 (3) Å
c = 16.0672 (5) Å
V = 1853.73 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 298 K
0.16 × 0.12 × 0.10 mm

Data collection

Bruker SMART 4K CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.969, T_max = 0.980
10064 measured reflections
4472 independent reflections
4226 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.136
S = 1.13
4472 reflections
241 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.37 e Å⁻³
Absolute structure: Flack (1983 ), 1861 Freidel pairs
Flack parameter: 0.08 (10)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O2ⁱ	0.93	2.58	3.359 (3)	142
C2—H2⋯O2ⁱⁱ	0.93	2.50	3.432 (3)	177
N3—H3A⋯O1ⁱⁱⁱ	0.88 (3)	2.08 (3)	2.863 (3)	147 (3)
C16—H16C⋯O2	0.96	2.31	3.000 (3)	128
Symmetry codes: (i) $[-x+{\script{1\over 2}}, -y+1, z-{\script{1\over 2}}]$ ; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ .

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/S1600536809033595/at2864sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809033595/at2864Isup2.hkl

checkCIF report

Comment top

The derivatives of thienopyrimidine are of great importance because of their remarked biological properties (Ding et al., 2004). We have recently focused on the synthesis of fused heterocyclic systems containing a fused pyrimidinone ring moiety using aza-Wittig reaction. The title compound, may be used as a new precursor for obtaining bioactive molecules and its structure is reported here, Fig.1. The bond lengths and angles are unexceptional. The thienopyrimidinone rings are closer to coplanarity with maximum deviations 0.072 (2)Å and -0.058 (2)Å for C10 and N1, respectively. The phenyl ring is twisted with respect to the pyrimidinone ring, with a dihedral angle of 60.11 (9)°. 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 preparation and biological and pharmaceutical activities of pyrimidinone derivatives, see: Modica et al. (2004); Panico et al. (2001). For biological activity of thienopyrimidine derivatives, see: Ding et al. (2004).

Experimental top

To a solution of diethyl 5-((phenylimino)methyleneamino)- 3-methylthiophene-2,4-dicarboxylate(3 mmol) in anhydrous dichloromethane (15 ml) was added 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 78%. 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. ORTEP drawing and atom labelling scheme of the title compound with thermal ellipsoids drawn at the 50% probability level.

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

Crystal data top

C₁₉H₂₁N₃O₃S	F(000) = 784
M_r = 371.45	D_x = 1.331 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4659 reflections
a = 8.1682 (2) Å	θ = 2.5–28.0°
b = 14.1247 (3) Å	µ = 0.20 mm⁻¹
c = 16.0672 (5) Å	T = 298 K
V = 1853.73 (8) Å³	Block, colourless
Z = 4	0.16 × 0.12 × 0.10 mm

Data collection top

Bruker SMART 4K CCD area-detector diffractometer	4472 independent reflections
Radiation source: fine-focus sealed tube	4226 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
ϕ and ω scans	θ_max = 28.3°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→5
T_min = 0.969, T_max = 0.980	k = −18→18
10064 measured reflections	l = −21→21

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)] = 0.053	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.136	w = 1/[σ²(F_o²) + (0.0772P)² + 0.1133P] where P = (F_o² + 2F_c²)/3
S = 1.13	(Δ/σ)_max < 0.001
4472 reflections	Δρ_max = 0.39 e Å⁻³
241 parameters	Δρ_min = −0.37 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1861 Freidel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.08 (10)

Crystal data top

C₁₉H₂₁N₃O₃S	V = 1853.73 (8) Å³
M_r = 371.45	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 8.1682 (2) Å	µ = 0.20 mm⁻¹
b = 14.1247 (3) Å	T = 298 K
c = 16.0672 (5) Å	0.16 × 0.12 × 0.10 mm

Data collection top

Bruker SMART 4K CCD area-detector diffractometer	4472 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4226 reflections with I > 2σ(I)
T_min = 0.969, T_max = 0.980	R_int = 0.031
10064 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.136	Δρ_max = 0.39 e Å⁻³
S = 1.13	Δρ_min = −0.37 e Å⁻³
4472 reflections	Absolute structure: Flack (1983), 1861 Freidel pairs
241 parameters	Absolute structure parameter: 0.08 (10)
0 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
C1	0.2534 (2)	0.22884 (14)	0.48554 (12)	0.0322 (4)
C2	0.3341 (3)	0.15050 (17)	0.45355 (15)	0.0412 (5)
H2	0.3794	0.1052	0.4887	0.049*
C3	0.3457 (3)	0.14132 (19)	0.36796 (15)	0.0515 (6)
H3	0.4008	0.0895	0.3457	0.062*
C4	0.2783 (4)	0.2063 (2)	0.31554 (15)	0.0545 (6)
H4	0.2864	0.1984	0.2582	0.065*
C5	0.1984 (3)	0.28367 (18)	0.34767 (15)	0.0502 (6)
H5	0.1530	0.3283	0.3119	0.060*
C6	0.1848 (3)	0.29565 (16)	0.43303 (13)	0.0388 (5)
H6	0.1304	0.3479	0.4547	0.047*
C7	0.3242 (3)	0.32075 (14)	0.61007 (13)	0.0347 (4)
C8	0.3275 (3)	0.32060 (16)	0.69897 (13)	0.0358 (4)
C9	0.2629 (3)	0.24251 (15)	0.74015 (12)	0.0374 (4)
C10	0.1679 (2)	0.17242 (14)	0.62462 (12)	0.0342 (4)
C11	0.3990 (3)	0.38959 (15)	0.75391 (13)	0.0362 (4)
C12	0.3869 (3)	0.36077 (15)	0.83528 (14)	0.0407 (5)
C13	−0.0094 (3)	0.03243 (17)	0.62828 (15)	0.0483 (6)
H13A	−0.1188	0.0260	0.6055	0.058*
H13B	−0.0201	0.0488	0.6867	0.058*
C14	0.0757 (4)	−0.0588 (2)	0.6213 (2)	0.0725 (9)
H14A	0.0157	−0.1056	0.6532	0.087*
H14B	0.1834	−0.0526	0.6462	0.087*
C15	0.0958 (7)	−0.0951 (3)	0.5329 (3)	0.1005 (15)
H15A	−0.0083	−0.1161	0.5121	0.151*
H15B	0.1716	−0.1471	0.5325	0.151*
H15C	0.1368	−0.0452	0.4981	0.151*
C16	0.4758 (4)	0.47961 (18)	0.72536 (16)	0.0507 (6)
H16A	0.3920	0.5227	0.7075	0.076*
H16B	0.5486	0.4667	0.6798	0.076*
H16C	0.5363	0.5074	0.7704	0.076*
C17	0.4320 (3)	0.41350 (18)	0.91026 (15)	0.0443 (5)
C18	0.4227 (5)	0.4121 (2)	1.05795 (16)	0.0689 (9)
H18A	0.3688	0.4733	1.0586	0.083*
H18B	0.5391	0.4218	1.0662	0.083*
C19	0.3562 (5)	0.3512 (3)	1.12406 (18)	0.0761 (9)
H19A	0.2411	0.3419	1.1151	0.114*
H19B	0.3731	0.3809	1.1771	0.114*
H19C	0.4110	0.2911	1.1231	0.114*
N1	0.2447 (2)	0.24077 (12)	0.57496 (10)	0.0340 (4)
N2	0.1836 (2)	0.16896 (13)	0.70577 (11)	0.0393 (4)
N3	0.0749 (2)	0.10894 (14)	0.58518 (13)	0.0422 (4)
H3A	0.055 (3)	0.121 (2)	0.5323 (18)	0.051*
O1	0.3846 (2)	0.38072 (11)	0.56420 (9)	0.0453 (4)
O2	0.4921 (3)	0.49108 (14)	0.91163 (11)	0.0578 (5)
O3	0.3935 (3)	0.36454 (14)	0.97886 (11)	0.0609 (5)
S1	0.29211 (8)	0.25028 (4)	0.84614 (3)	0.04848 (17)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0379 (9)	0.0327 (10)	0.0261 (9)	−0.0042 (7)	0.0009 (7)	0.0019 (7)
C2	0.0486 (12)	0.0380 (12)	0.0369 (11)	0.0050 (9)	−0.0041 (9)	0.0002 (9)
C3	0.0667 (15)	0.0487 (14)	0.0391 (12)	0.0029 (11)	0.0069 (11)	−0.0120 (10)
C4	0.0743 (17)	0.0613 (16)	0.0278 (10)	−0.0083 (14)	0.0003 (11)	−0.0038 (10)
C5	0.0619 (13)	0.0515 (13)	0.0372 (11)	−0.0084 (11)	−0.0076 (11)	0.0142 (11)
C6	0.0430 (11)	0.0356 (11)	0.0378 (11)	0.0019 (9)	−0.0006 (9)	0.0052 (8)
C7	0.0427 (11)	0.0287 (9)	0.0327 (10)	0.0026 (8)	0.0031 (8)	−0.0027 (8)
C8	0.0447 (11)	0.0326 (10)	0.0301 (10)	−0.0012 (9)	0.0029 (8)	−0.0024 (8)
C9	0.0489 (11)	0.0390 (11)	0.0242 (8)	0.0002 (10)	−0.0013 (8)	0.0001 (8)
C10	0.0439 (11)	0.0290 (10)	0.0297 (10)	−0.0004 (8)	0.0015 (8)	0.0028 (8)
C11	0.0412 (10)	0.0328 (10)	0.0344 (11)	0.0030 (8)	0.0017 (8)	−0.0056 (8)
C12	0.0498 (11)	0.0389 (11)	0.0334 (11)	−0.0011 (9)	0.0002 (9)	−0.0048 (9)
C13	0.0618 (14)	0.0451 (13)	0.0381 (12)	−0.0169 (11)	0.0044 (11)	0.0009 (10)
C14	0.079 (2)	0.0551 (17)	0.083 (2)	−0.0100 (15)	−0.0015 (17)	0.0234 (16)
C15	0.139 (4)	0.053 (2)	0.109 (3)	−0.005 (2)	0.043 (3)	−0.018 (2)
C16	0.0734 (17)	0.0381 (12)	0.0406 (13)	−0.0103 (11)	0.0032 (11)	−0.0060 (10)
C17	0.0517 (12)	0.0460 (13)	0.0354 (11)	0.0043 (10)	−0.0032 (10)	−0.0104 (10)
C18	0.104 (2)	0.0697 (19)	0.0329 (13)	−0.0100 (18)	−0.0062 (14)	−0.0123 (12)
C19	0.101 (2)	0.086 (2)	0.0413 (15)	0.000 (2)	−0.0002 (16)	−0.0025 (15)
N1	0.0460 (8)	0.0304 (8)	0.0258 (8)	−0.0008 (7)	0.0016 (6)	0.0007 (6)
N2	0.0547 (11)	0.0356 (9)	0.0276 (8)	−0.0092 (8)	−0.0007 (8)	0.0024 (7)
N3	0.0570 (11)	0.0387 (10)	0.0309 (9)	−0.0101 (8)	−0.0060 (8)	0.0028 (8)
O1	0.0673 (10)	0.0378 (9)	0.0308 (8)	−0.0124 (8)	0.0093 (7)	0.0004 (6)
O2	0.0789 (12)	0.0515 (11)	0.0429 (10)	−0.0127 (9)	−0.0058 (9)	−0.0113 (8)
O3	0.0943 (14)	0.0570 (11)	0.0313 (9)	−0.0150 (10)	−0.0040 (9)	−0.0089 (8)
S1	0.0721 (4)	0.0474 (3)	0.0259 (2)	−0.0128 (3)	−0.0033 (2)	0.0012 (2)

Geometric parameters (Å, º) top

C1—C6	1.384 (3)	C12—S1	1.751 (2)
C1—C2	1.387 (3)	C13—N3	1.456 (3)
C1—N1	1.448 (2)	C13—C14	1.468 (4)
C2—C3	1.385 (3)	C13—H13A	0.9700
C2—H2	0.9300	C13—H13B	0.9700
C3—C4	1.362 (4)	C14—C15	1.519 (5)
C3—H3	0.9300	C14—H14A	0.9700
C4—C5	1.373 (4)	C14—H14B	0.9700
C4—H4	0.9300	C15—H15A	0.9600
C5—C6	1.386 (3)	C15—H15B	0.9600
C5—H5	0.9300	C15—H15C	0.9600
C6—H6	0.9300	C16—H16A	0.9600
C7—O1	1.226 (3)	C16—H16B	0.9600
C7—N1	1.420 (3)	C16—H16C	0.9600
C7—C8	1.429 (3)	C17—O2	1.201 (3)
C8—C9	1.390 (3)	C17—O3	1.339 (3)
C8—C11	1.439 (3)	C18—O3	1.457 (3)
C9—N2	1.343 (3)	C18—C19	1.471 (5)
C9—S1	1.723 (2)	C18—H18A	0.9700
C10—N2	1.311 (3)	C18—H18B	0.9700
C10—N3	1.335 (3)	C19—H19A	0.9600
C10—N1	1.401 (3)	C19—H19B	0.9600
C11—C12	1.373 (3)	C19—H19C	0.9600
C11—C16	1.490 (3)	N3—H3A	0.88 (3)
C12—C17	1.463 (3)

C6—C1—C2	120.7 (2)	C13—C14—C15	114.8 (3)
C6—C1—N1	120.37 (18)	C13—C14—H14A	108.6
C2—C1—N1	118.93 (18)	C15—C14—H14A	108.6
C3—C2—C1	118.4 (2)	C13—C14—H14B	108.6
C3—C2—H2	120.8	C15—C14—H14B	108.6
C1—C2—H2	120.8	H14A—C14—H14B	107.6
C4—C3—C2	121.5 (2)	C14—C15—H15A	109.5
C4—C3—H3	119.2	C14—C15—H15B	109.5
C2—C3—H3	119.2	H15A—C15—H15B	109.5
C3—C4—C5	119.7 (2)	C14—C15—H15C	109.5
C3—C4—H4	120.1	H15A—C15—H15C	109.5
C5—C4—H4	120.1	H15B—C15—H15C	109.5
C4—C5—C6	120.5 (2)	C11—C16—H16A	109.5
C4—C5—H5	119.8	C11—C16—H16B	109.5
C6—C5—H5	119.8	H16A—C16—H16B	109.5
C1—C6—C5	119.2 (2)	C11—C16—H16C	109.5
C1—C6—H6	120.4	H16A—C16—H16C	109.5
C5—C6—H6	120.4	H16B—C16—H16C	109.5
O1—C7—N1	119.66 (19)	O2—C17—O3	123.5 (2)
O1—C7—C8	126.5 (2)	O2—C17—C12	125.6 (2)
N1—C7—C8	113.87 (18)	O3—C17—C12	110.8 (2)
C9—C8—C7	118.0 (2)	O3—C18—C19	107.5 (3)
C9—C8—C11	113.54 (18)	O3—C18—H18A	110.2
C7—C8—C11	128.3 (2)	C19—C18—H18A	110.2
N2—C9—C8	126.94 (19)	O3—C18—H18B	110.2
N2—C9—S1	121.50 (16)	C19—C18—H18B	110.2
C8—C9—S1	111.54 (16)	H18A—C18—H18B	108.5
N2—C10—N3	120.16 (19)	C18—C19—H19A	109.5
N2—C10—N1	123.25 (18)	C18—C19—H19B	109.5
N3—C10—N1	116.58 (18)	H19A—C19—H19B	109.5
C12—C11—C8	110.74 (19)	C18—C19—H19C	109.5
C12—C11—C16	125.2 (2)	H19A—C19—H19C	109.5
C8—C11—C16	124.04 (19)	H19B—C19—H19C	109.5
C11—C12—C17	127.9 (2)	C10—N1—C7	121.80 (16)
C11—C12—S1	113.03 (16)	C10—N1—C1	120.45 (16)
C17—C12—S1	118.88 (17)	C7—N1—C1	117.67 (16)
N3—C13—C14	113.0 (2)	C10—N2—C9	115.30 (18)
N3—C13—H13A	109.0	C10—N3—C13	122.80 (19)
C14—C13—H13A	109.0	C10—N3—H3A	115.4 (19)
N3—C13—H13B	109.0	C13—N3—H3A	121.2 (19)
C14—C13—H13B	109.0	C17—O3—C18	116.2 (2)
H13A—C13—H13B	107.8	C9—S1—C12	91.12 (11)

C6—C1—C2—C3	0.6 (3)	S1—C12—C17—O3	1.2 (3)
N1—C1—C2—C3	−178.1 (2)	N2—C10—N1—C7	−10.4 (3)
C1—C2—C3—C4	−0.9 (4)	N3—C10—N1—C7	169.45 (18)
C2—C3—C4—C5	0.8 (4)	N2—C10—N1—C1	166.03 (19)
C3—C4—C5—C6	−0.5 (4)	N3—C10—N1—C1	−14.1 (3)
C2—C1—C6—C5	−0.3 (3)	O1—C7—N1—C10	−177.29 (19)
N1—C1—C6—C5	178.4 (2)	C8—C7—N1—C10	4.1 (3)
C4—C5—C6—C1	0.2 (4)	O1—C7—N1—C1	6.2 (3)
O1—C7—C8—C9	−175.2 (2)	C8—C7—N1—C1	−172.42 (17)
N1—C7—C8—C9	3.3 (3)	C6—C1—N1—C10	120.7 (2)
O1—C7—C8—C11	0.8 (4)	C2—C1—N1—C10	−60.5 (3)
N1—C7—C8—C11	179.28 (19)	C6—C1—N1—C7	−62.7 (3)
C7—C8—C9—N2	−6.1 (3)	C2—C1—N1—C7	116.0 (2)
C11—C8—C9—N2	177.4 (2)	N3—C10—N2—C9	−172.1 (2)
C7—C8—C9—S1	175.14 (16)	N1—C10—N2—C9	7.7 (3)
C11—C8—C9—S1	−1.4 (2)	C8—C9—N2—C10	0.5 (3)
C9—C8—C11—C12	0.4 (3)	S1—C9—N2—C10	179.13 (17)
C7—C8—C11—C12	−175.7 (2)	N2—C10—N3—C13	−1.6 (3)
C9—C8—C11—C16	−179.8 (2)	N1—C10—N3—C13	178.5 (2)
C7—C8—C11—C16	4.1 (4)	C14—C13—N3—C10	−100.7 (3)
C8—C11—C12—C17	−174.6 (2)	O2—C17—O3—C18	2.3 (4)
C16—C11—C12—C17	5.6 (4)	C12—C17—O3—C18	−176.2 (3)
C8—C11—C12—S1	0.8 (2)	C19—C18—O3—C17	173.9 (3)
C16—C11—C12—S1	−179.1 (2)	N2—C9—S1—C12	−177.32 (19)
N3—C13—C14—C15	−60.7 (4)	C8—C9—S1—C12	1.53 (17)
C11—C12—C17—O2	−2.1 (4)	C11—C12—S1—C9	−1.33 (19)
S1—C12—C17—O2	−177.2 (2)	C17—C12—S1—C9	174.47 (19)
C11—C12—C17—O3	176.3 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O2ⁱ	0.93	2.58	3.359 (3)	142
C2—H2···O2ⁱⁱ	0.93	2.50	3.432 (3)	177
N3—H3A···O1ⁱⁱⁱ	0.88 (3)	2.08 (3)	2.863 (3)	147 (3)
C16—H16C···O2	0.96	2.31	3.000 (3)	128

Symmetry codes: (i) −x+1/2, −y+1, z−1/2; (ii) −x+1, y−1/2, −z+3/2; (iii) 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)	8.1682 (2), 14.1247 (3), 16.0672 (5)
V (Å³)	1853.73 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.16 × 0.12 × 0.10

Data collection
Diffractometer	Bruker SMART 4K CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.969, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	10064, 4472, 4226
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.666

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.136, 1.13
No. of reflections	4472
No. of parameters	241
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.37
Absolute structure	Flack (1983), 1861 Freidel pairs
Absolute structure parameter	0.08 (10)

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
C6—H6···O2ⁱ	0.93	2.58	3.359 (3)	141.7
C2—H2···O2ⁱⁱ	0.93	2.50	3.432 (3)	176.7
N3—H3A···O1ⁱⁱⁱ	0.88 (3)	2.08 (3)	2.863 (3)	147 (3)
C16—H16C···O2	0.96	2.31	3.000 (3)	128.3

Symmetry codes: (i) −x+1/2, −y+1, z−1/2; (ii) −x+1, y−1/2, −z+3/2; (iii) 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) and the Science Research Project of Yunyang Medical College (No. 2007QDJ14).

References

Bruker (2001). SMART and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Ding, M. W., Xu, S. Z. & Zhao, J. F. (2004). J. Org. Chem. 69, 8366–8371. Web of Science CrossRef PubMed CAS Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science 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). Farmaco, 56, 959–964. Web of Science CrossRef PubMed CAS 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

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 65| Part 9| September 2009| Page o2266

doi:10.1107/S1600536809033595

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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