2-Diethyl­amino-6-ethyl-6-methyl-3-phenylthieno[2,3-d]pyrimidin-4(3H)-one

In the title compound, C₁₉H₂₃N₃OS, the two fused rings of the thieno[2,3-d]pyrimidin-4(3H)-one system are almost coplanar. The packing of the mol­ecules in the crystal structure is determined by van der Waals forces. No inter­molecular hydrogen-bonding inter­actions or π–π stacking inter­actions are present in the crystal structure.

Key indicators

• Single-crystal X-ray study
• T = 292 K
• Mean [sigma](C-C)= 0.003 Å
• R factor = 0.054
• wR factor = 0.137
• Data-to-parameter ratio = 18.9

checkCIF/PLATON results

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Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL.

2-Diethylamino-6-ethyl-6-methyl-3-phenylthieno[2,3-d]pyrimidin-4(3H)-one

Crystal data

C19H23N3OS	F(000) = 728
Mr = 341.46	Dx = 1.233 Mg m^−3 Dm = 1.233 Mg m^−3 Dm measured by not measured
Monoclinic, P21/c	Melting point: 418 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 8.8085 (10) Å	Cell parameters from 3015 reflections
b = 9.5503 (11) Å	θ = 2.3–24.8°
c = 22.037 (3) Å	µ = 0.19 mm^−1
β = 97.269 (2)°	T = 292 K
V = 1839.0 (4) Å^3	Block, yellow
Z = 4	0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer	3015 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.055
Graphite monochromator	θmax = 27.5°, θmin = 1.9°
φ and ω scans	h = −11→11
11310 measured reflections	k = −11→12
4174 independent reflections	l = −28→22

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.137	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0682P)^2] where P = (Fo^2 + 2Fc^2)/3
4174 reflections	(Δ/σ)max = 0.001
221 parameters	Δρmax = 0.19 e Å^−3
0 restraints	Δρmin = −0.31 e Å^−3

Special details

Experimental. Spectroscopic analysis: ¹H NMR (CDCl₃, 400 MHz): 0.787–0.822 (t, 6H, 2CH₃, J = 14.0 Hz), 1.110–1.147 (t, 3H, CH₃, J = 14.8 Hz), 2.365 (s, 3H, CH₃), 2.846–2.864 (d, 2H, CH₂, J = 7.2 Hz), 3.018–3.070 (q, 4H, 2CH₂, J = 20.8 Hz), 7.264–7.498 (m, 5H, Ar—H); IR (KBr, ν, cm^-1): 1681 (C ═ O), 1540 (C ═N), 2965 (C—H, alkyl).

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.2748 (3)	0.2136 (2)	0.47246 (12)	0.0772 (7)
H1A	0.1909	0.2297	0.4955	0.116*
H1B	0.3375	0.1390	0.4910	0.116*
H1C	0.2358	0.1882	0.4313	0.116*
C2	0.3693 (2)	0.3452 (2)	0.47186 (9)	0.0562 (5)
H2A	0.4083	0.3702	0.5136	0.067*
H2B	0.4563	0.3270	0.4501	0.067*
C3	0.2044 (3)	0.5770 (3)	0.54139 (9)	0.0739 (7)
H3A	0.2433	0.4926	0.5613	0.111*
H3B	0.1007	0.5915	0.5491	0.111*
H3C	0.2662	0.6549	0.5570	0.111*
C4	0.2803 (2)	0.4659 (2)	0.44234 (8)	0.0456 (4)
C5	0.2090 (2)	0.5642 (2)	0.47370 (9)	0.0543 (5)
C6	0.1628 (2)	0.60491 (19)	0.36148 (8)	0.0432 (4)
C7	0.25372 (19)	0.49043 (18)	0.37756 (8)	0.0396 (4)
C8	0.3169 (2)	0.41712 (18)	0.32959 (8)	0.0415 (4)
C9	0.16679 (19)	0.58387 (17)	0.25994 (8)	0.0395 (4)
C10	0.35126 (19)	0.42110 (18)	0.22131 (7)	0.0396 (4)
C11	0.3336 (2)	0.2844 (2)	0.20222 (9)	0.0521 (5)
H11	0.2669	0.2254	0.2196	0.062*
C12	0.4153 (3)	0.2350 (2)	0.15717 (10)	0.0665 (6)
H12	0.4041	0.1426	0.1442	0.080*
C13	0.5132 (3)	0.3230 (3)	0.13161 (10)	0.0693 (7)
H13	0.5677	0.2900	0.1011	0.083*
C14	0.5309 (2)	0.4598 (3)	0.15098 (9)	0.0626 (6)
H14	0.5973	0.5187	0.1334	0.075*
C15	0.4502 (2)	0.5102 (2)	0.19660 (8)	0.0477 (4)
H15	0.4627	0.6022	0.2102	0.057*
C16	0.0477 (2)	0.5203 (2)	0.15713 (9)	0.0518 (5)
H16A	−0.0617	0.5372	0.1527	0.062*
H16B	0.0661	0.4271	0.1740	0.062*
C17	0.1021 (3)	0.5266 (2)	0.09473 (9)	0.0670 (6)
H17A	0.0849	0.6189	0.0780	0.101*
H17B	0.0464	0.4596	0.0681	0.101*
H17C	0.2094	0.5053	0.0985	0.101*
C18	0.0651 (2)	0.7675 (2)	0.19106 (9)	0.0509 (5)
H18A	−0.0163	0.7812	0.2163	0.061*
H18B	0.0216	0.7789	0.1487	0.061*
C19	0.1857 (3)	0.8767 (2)	0.20685 (10)	0.0636 (6)
H19A	0.2169	0.8763	0.2502	0.095*
H19B	0.1451	0.9671	0.1946	0.095*
H19C	0.2723	0.8568	0.1859	0.095*
N1	0.26886 (15)	0.47293 (14)	0.26980 (6)	0.0381 (3)
N2	0.11491 (17)	0.65260 (15)	0.30406 (7)	0.0450 (4)
N3	0.12541 (16)	0.62379 (15)	0.20014 (7)	0.0436 (4)
O1	0.40594 (18)	0.31988 (14)	0.33535 (6)	0.0634 (4)
S1	0.10895 (7)	0.68593 (6)	0.42534 (2)	0.0605 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0916 (18)	0.0622 (15)	0.0769 (17)	−0.0034 (13)	0.0068 (14)	0.0146 (12)
C2	0.0601 (12)	0.0658 (14)	0.0412 (11)	−0.0017 (10)	0.0010 (9)	0.0058 (9)
C3	0.0953 (18)	0.0848 (17)	0.0448 (12)	−0.0026 (14)	0.0210 (12)	−0.0080 (11)
C4	0.0475 (10)	0.0513 (11)	0.0385 (10)	−0.0069 (8)	0.0073 (8)	0.0003 (8)
C5	0.0618 (12)	0.0621 (13)	0.0408 (11)	−0.0052 (10)	0.0139 (9)	−0.0021 (9)
C6	0.0468 (10)	0.0428 (10)	0.0422 (10)	−0.0022 (8)	0.0138 (8)	−0.0019 (8)
C7	0.0423 (9)	0.0401 (10)	0.0369 (9)	−0.0052 (7)	0.0069 (7)	−0.0010 (7)
C8	0.0472 (10)	0.0378 (10)	0.0397 (10)	0.0024 (8)	0.0059 (8)	0.0041 (7)
C9	0.0398 (9)	0.0353 (9)	0.0440 (10)	−0.0016 (7)	0.0072 (7)	0.0026 (7)
C10	0.0442 (9)	0.0403 (10)	0.0338 (9)	0.0053 (8)	0.0033 (7)	0.0004 (7)
C11	0.0687 (13)	0.0414 (11)	0.0469 (11)	0.0020 (9)	0.0103 (9)	−0.0017 (8)
C12	0.0863 (16)	0.0576 (14)	0.0552 (13)	0.0176 (12)	0.0072 (12)	−0.0136 (11)
C13	0.0682 (14)	0.0951 (19)	0.0459 (12)	0.0283 (13)	0.0127 (10)	−0.0083 (12)
C14	0.0509 (12)	0.0902 (17)	0.0489 (12)	0.0024 (11)	0.0144 (10)	0.0062 (11)
C15	0.0457 (10)	0.0517 (11)	0.0456 (10)	−0.0022 (8)	0.0055 (8)	0.0003 (8)
C16	0.0529 (11)	0.0497 (12)	0.0504 (11)	−0.0035 (9)	−0.0029 (9)	0.0032 (9)
C17	0.0855 (16)	0.0660 (15)	0.0473 (12)	−0.0046 (12)	−0.0004 (11)	−0.0052 (10)
C18	0.0566 (11)	0.0470 (11)	0.0483 (11)	0.0117 (9)	0.0044 (9)	0.0073 (9)
C19	0.0831 (15)	0.0441 (12)	0.0632 (13)	0.0022 (11)	0.0082 (11)	0.0061 (10)
N1	0.0437 (8)	0.0354 (8)	0.0355 (8)	0.0025 (6)	0.0063 (6)	0.0009 (6)
N2	0.0491 (9)	0.0427 (9)	0.0447 (9)	0.0064 (7)	0.0121 (7)	0.0032 (7)
N3	0.0492 (9)	0.0405 (9)	0.0402 (8)	0.0056 (7)	0.0017 (7)	0.0031 (7)
O1	0.0832 (10)	0.0615 (9)	0.0461 (8)	0.0317 (8)	0.0101 (7)	0.0075 (6)
S1	0.0763 (4)	0.0582 (4)	0.0517 (3)	0.0104 (3)	0.0265 (3)	−0.0038 (2)

Geometric parameters (Å, º)

C1—C2	1.509 (3)	C10—N1	1.453 (2)
C1—H1A	0.9600	C11—C12	1.381 (3)
C1—H1B	0.9600	C11—H11	0.9300
C1—H1C	0.9600	C12—C13	1.374 (3)
C2—C4	1.496 (3)	C12—H12	0.9300
C2—H2A	0.9700	C13—C14	1.377 (3)
C2—H2B	0.9700	C13—H13	0.9300
C3—C5	1.502 (3)	C14—C15	1.389 (3)
C3—H3A	0.9600	C14—H14	0.9300
C3—H3B	0.9600	C15—H15	0.9300
C3—H3C	0.9600	C16—N3	1.476 (2)
C4—C5	1.365 (3)	C16—C17	1.514 (3)
C4—C7	1.436 (2)	C16—H16A	0.9700
C5—S1	1.739 (2)	C16—H16B	0.9700
C6—N2	1.361 (2)	C17—H17A	0.9600
C6—C7	1.375 (2)	C17—H17B	0.9600
C6—S1	1.7240 (18)	C17—H17C	0.9600
C7—C8	1.437 (2)	C18—N3	1.476 (2)
C8—O1	1.212 (2)	C18—C19	1.498 (3)
C8—N1	1.435 (2)	C18—H18A	0.9700
C9—N2	1.303 (2)	C18—H18B	0.9700
C9—N3	1.376 (2)	C19—H19A	0.9600
C9—N1	1.389 (2)	C19—H19B	0.9600
C10—C11	1.374 (2)	C19—H19C	0.9600
C10—C15	1.379 (2)
C2—C1—H1A	109.5	C13—C12—H12	120.1
C2—C1—H1B	109.5	C11—C12—H12	120.1
H1A—C1—H1B	109.5	C12—C13—C14	120.3 (2)
C2—C1—H1C	109.5	C12—C13—H13	119.8
H1A—C1—H1C	109.5	C14—C13—H13	119.8
H1B—C1—H1C	109.5	C13—C14—C15	120.3 (2)
C4—C2—C1	112.75 (18)	C13—C14—H14	119.8
C4—C2—H2A	109.0	C15—C14—H14	119.8
C1—C2—H2A	109.0	C10—C15—C14	118.60 (19)
C4—C2—H2B	109.0	C10—C15—H15	120.7
C1—C2—H2B	109.0	C14—C15—H15	120.7
H2A—C2—H2B	107.8	N3—C16—C17	112.47 (16)
C5—C3—H3A	109.5	N3—C16—H16A	109.1
C5—C3—H3B	109.5	C17—C16—H16A	109.1
H3A—C3—H3B	109.5	N3—C16—H16B	109.1
C5—C3—H3C	109.5	C17—C16—H16B	109.1
H3A—C3—H3C	109.5	H16A—C16—H16B	107.8
H3B—C3—H3C	109.5	C16—C17—H17A	109.5
C5—C4—C7	111.33 (17)	C16—C17—H17B	109.5
C5—C4—C2	124.00 (17)	H17A—C17—H17B	109.5
C7—C4—C2	124.63 (17)	C16—C17—H17C	109.5
C4—C5—C3	129.1 (2)	H17A—C17—H17C	109.5
C4—C5—S1	112.28 (14)	H17B—C17—H17C	109.5
C3—C5—S1	118.62 (16)	N3—C18—C19	112.54 (16)
N2—C6—C7	127.41 (16)	N3—C18—H18A	109.1
N2—C6—S1	121.61 (14)	C19—C18—H18A	109.1
C7—C6—S1	110.97 (13)	N3—C18—H18B	109.1
C6—C7—C4	113.70 (16)	C19—C18—H18B	109.1
C6—C7—C8	117.71 (15)	H18A—C18—H18B	107.8
C4—C7—C8	128.47 (16)	C18—C19—H19A	109.5
O1—C8—N1	119.51 (16)	C18—C19—H19B	109.5
O1—C8—C7	127.02 (16)	H19A—C19—H19B	109.5
N1—C8—C7	113.44 (15)	C18—C19—H19C	109.5
N2—C9—N3	119.98 (16)	H19A—C19—H19C	109.5
N2—C9—N1	123.28 (16)	H19B—C19—H19C	109.5
N3—C9—N1	116.69 (15)	C9—N1—C8	122.48 (14)
C11—C10—C15	121.21 (16)	C9—N1—C10	121.24 (14)
C11—C10—N1	120.08 (15)	C8—N1—C10	115.62 (14)
C15—C10—N1	118.68 (16)	C9—N2—C6	115.40 (15)
C10—C11—C12	119.69 (19)	C9—N3—C18	115.77 (14)
C10—C11—H11	120.2	C9—N3—C16	118.33 (14)
C12—C11—H11	120.2	C18—N3—C16	113.93 (14)
C13—C12—C11	119.8 (2)	C6—S1—C5	91.72 (9)
C1—C2—C4—C5	94.7 (2)	N3—C9—N1—C8	−177.50 (14)
C1—C2—C4—C7	−82.8 (2)	N2—C9—N1—C10	−165.23 (16)
C7—C4—C5—C3	178.9 (2)	N3—C9—N1—C10	12.2 (2)
C2—C4—C5—C3	1.1 (3)	O1—C8—N1—C9	179.79 (16)
C7—C4—C5—S1	0.3 (2)	C7—C8—N1—C9	−2.2 (2)
C2—C4—C5—S1	−177.44 (15)	O1—C8—N1—C10	−9.4 (2)
N2—C6—C7—C4	−178.44 (17)	C7—C8—N1—C10	168.60 (14)
S1—C6—C7—C4	0.5 (2)	C11—C10—N1—C9	−120.08 (19)
N2—C6—C7—C8	5.3 (3)	C15—C10—N1—C9	62.0 (2)
S1—C6—C7—C8	−175.78 (13)	C11—C10—N1—C8	69.0 (2)
C5—C4—C7—C6	−0.5 (2)	C15—C10—N1—C8	−108.95 (17)
C2—C4—C7—C6	177.22 (17)	N3—C9—N2—C6	−179.92 (15)
C5—C4—C7—C8	175.24 (17)	N1—C9—N2—C6	−2.5 (2)
C2—C4—C7—C8	−7.0 (3)	C7—C6—N2—C9	−2.7 (3)
C6—C7—C8—O1	175.38 (18)	S1—C6—N2—C9	178.44 (13)
C4—C7—C8—O1	−0.3 (3)	N2—C9—N3—C18	18.8 (2)
C6—C7—C8—N1	−2.5 (2)	N1—C9—N3—C18	−158.79 (15)
C4—C7—C8—N1	−178.09 (16)	N2—C9—N3—C16	−121.77 (18)
C15—C10—C11—C12	−0.5 (3)	N1—C9—N3—C16	60.7 (2)
N1—C10—C11—C12	−178.37 (17)	C19—C18—N3—C9	69.6 (2)
C10—C11—C12—C13	−0.2 (3)	C19—C18—N3—C16	−148.17 (17)
C11—C12—C13—C14	0.4 (3)	C17—C16—N3—C9	−140.08 (17)
C12—C13—C14—C15	0.1 (3)	C17—C16—N3—C18	78.7 (2)
C11—C10—C15—C14	1.0 (3)	N2—C6—S1—C5	178.76 (15)
N1—C10—C15—C14	178.91 (16)	C7—C6—S1—C5	−0.25 (15)
C13—C14—C15—C10	−0.8 (3)	C4—C5—S1—C6	−0.06 (16)
N2—C9—N1—C8	5.0 (3)	C3—C5—S1—C6	−178.80 (17)