2-Ethyl­amino-3-phenyl-2-benzothieno[3,2-d]pyrimidin-4(3H)-one

In the title compound, C₁₈H₁₅N₃OS, the three fused rings of the benzothienopyrimidinone are essentially coplanar. The crystal structure is stabilized by C—H...O and C—H...S hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 292 K
• Mean [sigma](C-C) = 0.003 Å
• Disorder in main residue
• R factor = 0.060
• wR factor = 0.162
• Data-to-parameter ratio = 15.7

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        C11

Alert level C
PLAT301_ALERT_3_C Main Residue  Disorder .........................       8.00 Perc.
PLAT420_ALERT_2_C D-H Without Acceptor       N3     -   H3A    ...          ?
PLAT480_ALERT_4_C Long H...A H-Bond Reported H15    ..  S1      ..       2.93 Ang.

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL (Bruker, 2001) and Mercury (Macrae et al., 2006).

2-Ethylamino-3-phenyl-2-benzothieno[3,2-d]pyrimidin-4(3H)-one

Crystal data

C18H15N3OS	F(000) = 672
Mr = 321.39	Dx = 1.336 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3460 reflections
a = 10.2947 (11) Å	θ = 2.2–23.7°
b = 12.0592 (13) Å	µ = 0.21 mm^−1
c = 13.4330 (14) Å	T = 292 K
β = 106.599 (2)°	Block, colorless
V = 1598.2 (3) Å^3	0.30 × 0.20 × 0.20 mm
Z = 4

Data collection

Bruker SMART 4K CCD area-detector diffractometer	2592 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.060
Graphite monochromator	θmax = 27.5°, θmin = 2.2°
φ and ω scans	h = −13→13
13934 measured reflections	k = −15→14
3667 independent reflections	l = −17→17

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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.162	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0869P)^2 + 0.0213P] where P = (Fo^2 + 2Fc^2)/3
3667 reflections	(Δ/σ)max = 0.001
233 parameters	Δρmax = 0.34 e Å^−3
9 restraints	Δρmin = −0.18 e Å^−3

Special details

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	Occ. (<1)
C1	0.4593 (2)	0.63612 (19)	0.06513 (15)	0.0562 (5)
C2	0.5330 (2)	0.6843 (2)	0.00298 (17)	0.0673 (6)
H2	0.6237	0.6666	0.0127	0.081*
C3	0.4683 (3)	0.7578 (2)	−0.0721 (2)	0.0829 (8)
H3	0.5156	0.7894	−0.1145	0.100*
C4	0.3339 (3)	0.7865 (2)	−0.0866 (2)	0.0864 (8)
H4	0.2933	0.8376	−0.1379	0.104*
C5	0.2592 (3)	0.7407 (2)	−0.02659 (19)	0.0768 (7)
H5	0.1691	0.7604	−0.0363	0.092*
C6	0.3231 (2)	0.66403 (18)	0.04909 (16)	0.0583 (5)
C7	0.5048 (2)	0.55801 (17)	0.14888 (15)	0.0510 (5)
C8	0.40231 (19)	0.52836 (17)	0.19061 (15)	0.0515 (5)
C9	0.42392 (19)	0.45236 (17)	0.27416 (15)	0.0503 (5)
C10	0.65740 (19)	0.44964 (19)	0.26138 (16)	0.0548 (5)
C11	0.8894 (6)	0.4561 (6)	0.2586 (7)	0.0543 (17)	0.512 (14)
H11A	0.8646	0.4466	0.1838	0.065*	0.512 (14)
H11B	0.9002	0.5347	0.2741	0.065*	0.512 (14)
C12	1.0162 (6)	0.3970 (11)	0.3077 (10)	0.112 (4)	0.512 (14)
H12A	1.0361	0.4022	0.3818	0.168*	0.512 (14)
H12B	1.0887	0.4297	0.2860	0.168*	0.512 (14)
H12C	1.0066	0.3204	0.2873	0.168*	0.512 (14)
C11'	0.8966 (7)	0.4048 (12)	0.2532 (7)	0.089 (3)	0.488 (14)
H11C	0.9170	0.3288	0.2396	0.106*	0.488 (14)
H11D	0.8734	0.4456	0.1883	0.106*	0.488 (14)
C12'	1.0139 (8)	0.4565 (10)	0.3294 (9)	0.110 (3)	0.488 (14)
H12D	0.9978	0.5345	0.3337	0.165*	0.488 (14)
H12E	1.0940	0.4454	0.3075	0.165*	0.488 (14)
H12F	1.0261	0.4231	0.3963	0.165*	0.488 (14)
C13	0.59356 (19)	0.34433 (18)	0.39928 (15)	0.0510 (5)
C14	0.6441 (2)	0.3898 (2)	0.49611 (17)	0.0669 (6)
H14	0.6587	0.4658	0.5041	0.080*
C15	0.6729 (3)	0.3210 (3)	0.58137 (18)	0.0817 (8)
H15	0.7079	0.3509	0.6474	0.098*
C16	0.6509 (2)	0.2094 (3)	0.5704 (2)	0.0789 (8)
H16	0.6711	0.1638	0.6287	0.095*
C17	0.5991 (2)	0.1649 (2)	0.4733 (2)	0.0739 (7)
H17	0.5829	0.0890	0.4657	0.089*
C18	0.5708 (2)	0.23210 (19)	0.38691 (18)	0.0610 (6)
H18	0.5366	0.2019	0.3209	0.073*
N1	0.63425 (16)	0.51894 (16)	0.18331 (13)	0.0577 (5)
N2	0.55993 (15)	0.41620 (14)	0.30898 (12)	0.0496 (4)
N3	0.78229 (18)	0.4085 (2)	0.30106 (17)	0.0735 (6)
O1	0.34087 (14)	0.41967 (13)	0.31651 (12)	0.0645 (4)
S1	0.24932 (5)	0.59419 (5)	0.13297 (4)	0.0618 (2)
H3A	0.793 (2)	0.360 (2)	0.3486 (19)	0.076 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0579 (12)	0.0575 (13)	0.0524 (11)	−0.0075 (10)	0.0145 (10)	−0.0032 (10)
C2	0.0662 (14)	0.0751 (16)	0.0613 (13)	−0.0096 (12)	0.0192 (11)	0.0013 (12)
C3	0.0855 (18)	0.092 (2)	0.0712 (16)	−0.0130 (15)	0.0220 (14)	0.0213 (14)
C4	0.092 (2)	0.0802 (19)	0.0796 (17)	−0.0010 (15)	0.0125 (15)	0.0263 (14)
C5	0.0729 (15)	0.0732 (17)	0.0764 (16)	0.0011 (13)	0.0086 (13)	0.0143 (13)
C6	0.0591 (13)	0.0572 (13)	0.0558 (12)	−0.0037 (10)	0.0121 (10)	−0.0004 (10)
C7	0.0476 (11)	0.0524 (12)	0.0521 (11)	−0.0050 (9)	0.0130 (9)	−0.0067 (9)
C8	0.0425 (10)	0.0536 (12)	0.0573 (11)	−0.0010 (8)	0.0124 (8)	−0.0018 (9)
C9	0.0415 (10)	0.0550 (12)	0.0555 (11)	−0.0031 (9)	0.0154 (9)	−0.0036 (9)
C10	0.0407 (10)	0.0684 (14)	0.0559 (12)	−0.0050 (9)	0.0149 (9)	−0.0016 (10)
C11	0.039 (3)	0.055 (4)	0.078 (3)	0.014 (2)	0.032 (2)	0.013 (3)
C12	0.061 (4)	0.140 (7)	0.144 (7)	0.018 (4)	0.044 (4)	0.046 (6)
C11'	0.053 (4)	0.120 (9)	0.096 (5)	0.028 (5)	0.025 (3)	0.025 (6)
C12'	0.080 (5)	0.095 (7)	0.170 (8)	−0.027 (4)	0.060 (5)	−0.035 (6)
C13	0.0418 (10)	0.0597 (13)	0.0537 (11)	0.0028 (9)	0.0171 (8)	0.0011 (9)
C14	0.0730 (15)	0.0676 (15)	0.0579 (13)	0.0103 (11)	0.0153 (11)	−0.0065 (11)
C15	0.0908 (19)	0.099 (2)	0.0534 (14)	0.0283 (16)	0.0181 (12)	−0.0055 (14)
C16	0.0724 (16)	0.101 (2)	0.0689 (16)	0.0293 (15)	0.0286 (13)	0.0279 (15)
C17	0.0629 (14)	0.0683 (16)	0.0908 (18)	0.0042 (12)	0.0223 (13)	0.0178 (14)
C18	0.0575 (12)	0.0613 (14)	0.0627 (13)	−0.0020 (10)	0.0146 (10)	0.0016 (11)
N1	0.0464 (9)	0.0696 (12)	0.0592 (10)	−0.0054 (8)	0.0182 (8)	0.0038 (9)
N2	0.0410 (9)	0.0563 (10)	0.0521 (9)	−0.0005 (7)	0.0141 (7)	0.0017 (7)
N3	0.0410 (10)	0.1077 (18)	0.0743 (13)	0.0081 (10)	0.0207 (9)	0.0214 (13)
O1	0.0463 (8)	0.0753 (11)	0.0778 (10)	0.0007 (7)	0.0272 (7)	0.0128 (8)
S1	0.0479 (3)	0.0686 (4)	0.0685 (4)	0.0045 (2)	0.0160 (3)	0.0084 (3)

Geometric parameters (Å, º)

C1—C6	1.398 (3)	C11—H11B	0.9700
C1—C2	1.404 (3)	C12—H12A	0.9600
C1—C7	1.439 (3)	C12—H12B	0.9600
C2—C3	1.365 (3)	C12—H12C	0.9600
C2—H2	0.9300	C11'—C12'	1.479 (8)
C3—C4	1.384 (4)	C11'—N3	1.494 (6)
C3—H3	0.9300	C11'—H11C	0.9700
C4—C5	1.379 (4)	C11'—H11D	0.9700
C4—H4	0.9300	C12'—H12D	0.9600
C5—C6	1.393 (3)	C12'—H12E	0.9600
C5—H5	0.9300	C12'—H12F	0.9600
C6—S1	1.745 (2)	C13—C14	1.370 (3)
C7—N1	1.364 (2)	C13—C18	1.376 (3)
C7—C8	1.376 (3)	C13—N2	1.450 (3)
C8—C9	1.416 (3)	C14—C15	1.376 (3)
C8—S1	1.736 (2)	C14—H14	0.9300
C9—O1	1.220 (2)	C15—C16	1.365 (4)
C9—N2	1.412 (2)	C15—H15	0.9300
C10—N1	1.309 (3)	C16—C17	1.370 (4)
C10—N3	1.338 (3)	C16—H16	0.9300
C10—N2	1.395 (3)	C17—C18	1.376 (3)
C11—C12	1.468 (6)	C17—H17	0.9300
C11—N3	1.493 (5)	C18—H18	0.9300
C11—H11A	0.9700	N3—H3A	0.85 (3)
C6—C1—C2	119.8 (2)	N3—C11'—H11C	110.5
C6—C1—C7	111.46 (19)	C12'—C11'—H11D	110.5
C2—C1—C7	128.7 (2)	N3—C11'—H11D	110.5
C3—C2—C1	118.4 (2)	H11C—C11'—H11D	108.7
C3—C2—H2	120.8	C11'—C12'—H12D	109.5
C1—C2—H2	120.8	C11'—C12'—H12E	109.5
C2—C3—C4	121.6 (2)	H12D—C12'—H12E	109.5
C2—C3—H3	119.2	C11'—C12'—H12F	109.5
C4—C3—H3	119.2	H12D—C12'—H12F	109.5
C5—C4—C3	121.3 (2)	H12E—C12'—H12F	109.5
C5—C4—H4	119.3	C14—C13—C18	120.9 (2)
C3—C4—H4	119.3	C14—C13—N2	119.35 (19)
C4—C5—C6	117.8 (2)	C18—C13—N2	119.69 (18)
C4—C5—H5	121.1	C13—C14—C15	118.8 (2)
C6—C5—H5	121.1	C13—C14—H14	120.6
C5—C6—C1	121.1 (2)	C15—C14—H14	120.6
C5—C6—S1	126.15 (18)	C16—C15—C14	121.0 (2)
C1—C6—S1	112.76 (16)	C16—C15—H15	119.5
N1—C7—C8	124.11 (19)	C14—C15—H15	119.5
N1—C7—C1	124.00 (18)	C15—C16—C17	119.7 (2)
C8—C7—C1	111.88 (18)	C15—C16—H16	120.1
C7—C8—C9	121.72 (18)	C17—C16—H16	120.1
C7—C8—S1	113.77 (16)	C16—C17—C18	120.2 (3)
C9—C8—S1	124.50 (15)	C16—C17—H17	119.9
O1—C9—N2	120.42 (19)	C18—C17—H17	119.9
O1—C9—C8	127.32 (19)	C13—C18—C17	119.3 (2)
N2—C9—C8	112.25 (17)	C13—C18—H18	120.3
N1—C10—N3	119.3 (2)	C17—C18—H18	120.3
N1—C10—N2	124.19 (18)	C10—N1—C7	115.41 (17)
N3—C10—N2	116.4 (2)	C10—N2—C9	122.27 (17)
C12—C11—N3	107.5 (5)	C10—N2—C13	121.69 (16)
C12—C11—H11A	110.2	C9—N2—C13	116.03 (16)
N3—C11—H11A	110.2	C10—N3—C11	115.8 (3)
C12—C11—H11B	110.2	C10—N3—C11'	128.7 (5)
N3—C11—H11B	110.2	C10—N3—H3A	117.2 (17)
H11A—C11—H11B	108.5	C11—N3—H3A	126.9 (17)
C12'—C11'—N3	106.1 (6)	C11'—N3—H3A	110.6 (18)
C12'—C11'—H11C	110.5	C8—S1—C6	90.11 (10)
C6—C1—C2—C3	0.0 (3)	C16—C17—C18—C13	−0.8 (3)
C7—C1—C2—C3	−179.4 (2)	N3—C10—N1—C7	−179.0 (2)
C1—C2—C3—C4	1.0 (4)	N2—C10—N1—C7	−0.4 (3)
C2—C3—C4—C5	−0.9 (5)	C8—C7—N1—C10	−0.4 (3)
C3—C4—C5—C6	−0.3 (4)	C1—C7—N1—C10	178.99 (19)
C4—C5—C6—C1	1.3 (4)	N1—C10—N2—C9	2.1 (3)
C4—C5—C6—S1	−179.2 (2)	N3—C10—N2—C9	−179.27 (18)
C2—C1—C6—C5	−1.2 (3)	N1—C10—N2—C13	−176.22 (19)
C7—C1—C6—C5	178.3 (2)	N3—C10—N2—C13	2.4 (3)
C2—C1—C6—S1	179.28 (17)	O1—C9—N2—C10	178.59 (18)
C7—C1—C6—S1	−1.2 (2)	C8—C9—N2—C10	−2.7 (3)
C6—C1—C7—N1	−178.02 (19)	O1—C9—N2—C13	−3.0 (3)
C2—C1—C7—N1	1.4 (4)	C8—C9—N2—C13	175.72 (17)
C6—C1—C7—C8	1.4 (3)	C14—C13—N2—C10	84.9 (3)
C2—C1—C7—C8	−179.1 (2)	C18—C13—N2—C10	−96.9 (2)
N1—C7—C8—C9	−0.5 (3)	C14—C13—N2—C9	−93.5 (2)
C1—C7—C8—C9	−179.93 (18)	C18—C13—N2—C9	84.7 (2)
N1—C7—C8—S1	178.42 (16)	N1—C10—N3—C11	6.4 (5)
C1—C7—C8—S1	−1.0 (2)	N2—C10—N3—C11	−172.4 (4)
C7—C8—C9—O1	−179.4 (2)	N1—C10—N3—C11'	−18.3 (7)
S1—C8—C9—O1	1.8 (3)	N2—C10—N3—C11'	163.0 (6)
C7—C8—C9—N2	1.9 (3)	C12—C11—N3—C10	−177.3 (9)
S1—C8—C9—N2	−176.87 (13)	C12—C11—N3—C11'	−49.4 (12)
C18—C13—C14—C15	0.5 (3)	C12'—C11'—N3—C10	126.6 (9)
N2—C13—C14—C15	178.6 (2)	C12'—C11'—N3—C11	61.1 (14)
C13—C14—C15—C16	−0.4 (4)	C7—C8—S1—C6	0.27 (16)
C14—C15—C16—C17	−0.2 (4)	C9—C8—S1—C6	179.16 (19)
C15—C16—C17—C18	0.8 (4)	C5—C6—S1—C8	−179.0 (2)
C14—C13—C18—C17	0.1 (3)	C1—C6—S1—C8	0.56 (17)
N2—C13—C18—C17	−178.00 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12B···O1^i	0.96	2.51	3.322 (6)	142
C15—H15···S1^ii	0.93	2.93	3.828 (3)	163

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