3-Isopropyl-2-propoxy-5,6,7,8-tetra­hydro-1-benzothieno[2,3-d]pyrimidin-4(3H)-one

In the title compound, C₁₆H₂₂N₂O₂S, the fused thio­phene and pyrimidine rings are almost coplanar. The packing of the mol­ecules in the crystal structure is mainly due to inter­molecular C—H...O hydrogen-bonding inter­actions, resulting in the formation of a zigzag chain.

Key indicators

• Single-crystal X-ray study
• T = 292 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.050
• wR factor = 0.126
• Data-to-parameter ratio = 18.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    N2     -   C9      ..       7.18 su

Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.52 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O1     -   C10     ..       5.30 su
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C11

   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
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 19907; program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 2001) and CAMERON (Watkin et al., 1993); software used to prepare material for publication: SHELXTL.

3-Isopropyl-2-propoxy-5,6,7,8-tetrahydro-1-benzothieno[2,3-d]pyrimidin-4(3H)-one

Crystal data

C16H22N2O2S	F(000) = 656
Mr = 306.42	Dx = 1.273 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2182 reflections
a = 10.1586 (9) Å	θ = 2.3–22.3°
b = 14.4156 (13) Å	µ = 0.21 mm^−1
c = 11.9245 (11) Å	T = 292 K
β = 113.675 (2)°	Block, colourless
V = 1599.3 (3) Å^3	0.30 × 0.24 × 0.20 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	2208 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.052
Graphite monochromator	θmax = 27.0°, θmin = 2.2°
φ and ω scans	h = −12→12
9659 measured reflections	k = −15→18
3476 independent reflections	l = −13→15

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.126	H-atom parameters constrained
S = 0.92	w = 1/[σ^2(Fo^2) + (0.0632P)^2] where P = (Fo^2 + 2Fc^2)/3
3476 reflections	(Δ/σ)max = 0.001
193 parameters	Δρmax = 0.23 e Å^−3
0 restraints	Δρmin = −0.23 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
C1	0.7080 (2)	1.08157 (14)	0.18118 (18)	0.0489 (5)
C2	0.8181 (2)	1.12025 (15)	0.1394 (2)	0.0592 (6)
H2A	0.8835	1.1608	0.2018	0.071*
H2B	0.7709	1.1562	0.0651	0.071*
C3	0.9012 (2)	1.04025 (15)	0.1153 (2)	0.0597 (6)
H3A	0.9582	1.0633	0.0727	0.072*
H3B	0.9662	1.0141	0.1927	0.072*
C4	0.8009 (2)	0.96590 (16)	0.0395 (2)	0.0618 (6)
H4A	0.8565	0.9182	0.0210	0.074*
H4B	0.7357	0.9926	−0.0375	0.074*
C5	0.7140 (2)	0.92179 (14)	0.10299 (19)	0.0558 (5)
H5A	0.6324	0.8894	0.0430	0.067*
H5B	0.7730	0.8766	0.1620	0.067*
C6	0.6609 (2)	0.99311 (13)	0.16769 (17)	0.0436 (5)
C7	0.55744 (19)	0.97881 (13)	0.22007 (17)	0.0428 (5)
C8	0.5283 (2)	1.05851 (12)	0.27015 (17)	0.0442 (5)
C9	0.3667 (2)	0.99094 (13)	0.32644 (18)	0.0463 (5)
C10	0.4844 (2)	0.89520 (14)	0.22598 (17)	0.0483 (5)
C11	0.3034 (2)	0.82151 (14)	0.2881 (2)	0.0600 (6)
H11	0.3413	0.7732	0.2513	0.072*
C12	0.1500 (2)	0.82618 (17)	0.2048 (2)	0.0779 (8)
H12A	0.1010	0.8676	0.2380	0.117*
H12B	0.1083	0.7655	0.1959	0.117*
H12C	0.1411	0.8485	0.1262	0.117*
C13	0.3397 (3)	0.78673 (19)	0.4135 (2)	0.1084 (12)
H13A	0.3064	0.8300	0.4575	0.163*
H13B	0.4420	0.7799	0.4548	0.163*
H13C	0.2943	0.7277	0.4097	0.163*
C14	0.2452 (2)	1.07632 (15)	0.42559 (19)	0.0551 (5)
H14A	0.2085	1.1228	0.3616	0.066*
H14B	0.3345	1.0989	0.4879	0.066*
C15	0.1381 (2)	1.05858 (15)	0.48011 (18)	0.0552 (5)
H15A	0.1740	1.0101	0.5414	0.066*
H15B	0.0488	1.0371	0.4166	0.066*
C16	0.1099 (3)	1.14533 (15)	0.5386 (2)	0.0699 (7)
H16A	0.1978	1.1657	0.6030	0.105*
H16B	0.0402	1.1320	0.5719	0.105*
H16C	0.0739	1.1933	0.4780	0.105*
N1	0.43320 (17)	1.06688 (11)	0.32377 (14)	0.0483 (4)
N2	0.38591 (16)	0.90596 (10)	0.28235 (14)	0.0470 (4)
O1	0.50040 (17)	0.81948 (10)	0.18727 (15)	0.0691 (5)
O2	0.26968 (14)	0.98975 (9)	0.37519 (13)	0.0544 (4)
S1	0.62818 (6)	1.15096 (3)	0.25581 (6)	0.0581 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0541 (12)	0.0446 (12)	0.0557 (13)	0.0040 (9)	0.0301 (10)	−0.0016 (9)
C2	0.0655 (14)	0.0543 (13)	0.0742 (15)	−0.0020 (11)	0.0453 (12)	−0.0024 (11)
C3	0.0584 (13)	0.0645 (14)	0.0652 (14)	0.0053 (11)	0.0340 (12)	−0.0033 (11)
C4	0.0598 (13)	0.0731 (15)	0.0551 (13)	0.0091 (12)	0.0259 (11)	−0.0084 (11)
C5	0.0617 (13)	0.0501 (12)	0.0569 (13)	0.0067 (10)	0.0252 (11)	−0.0066 (10)
C6	0.0463 (11)	0.0402 (11)	0.0430 (11)	0.0033 (9)	0.0167 (9)	0.0005 (8)
C7	0.0441 (10)	0.0333 (10)	0.0468 (12)	−0.0003 (8)	0.0137 (9)	−0.0003 (8)
C8	0.0458 (11)	0.0358 (11)	0.0546 (12)	−0.0017 (8)	0.0241 (10)	−0.0001 (8)
C9	0.0430 (11)	0.0475 (12)	0.0489 (12)	−0.0038 (9)	0.0189 (9)	0.0048 (9)
C10	0.0494 (11)	0.0412 (12)	0.0498 (12)	0.0007 (9)	0.0152 (10)	0.0024 (9)
C11	0.0650 (14)	0.0396 (12)	0.0706 (15)	−0.0155 (10)	0.0222 (12)	0.0033 (10)
C12	0.0625 (15)	0.0682 (16)	0.0842 (18)	−0.0254 (12)	0.0100 (14)	0.0078 (13)
C13	0.116 (2)	0.085 (2)	0.089 (2)	−0.0339 (18)	0.0056 (18)	0.0455 (17)
C14	0.0548 (12)	0.0557 (13)	0.0617 (14)	−0.0094 (10)	0.0307 (11)	0.0005 (10)
C15	0.0575 (13)	0.0611 (13)	0.0534 (13)	−0.0099 (10)	0.0289 (11)	0.0016 (10)
C16	0.0833 (17)	0.0639 (15)	0.0771 (17)	−0.0027 (13)	0.0473 (14)	0.0044 (12)
N1	0.0523 (10)	0.0380 (9)	0.0628 (11)	−0.0063 (7)	0.0316 (9)	−0.0026 (8)
N2	0.0499 (9)	0.0317 (9)	0.0547 (10)	−0.0059 (7)	0.0161 (8)	0.0020 (7)
O1	0.0881 (12)	0.0356 (8)	0.0899 (12)	−0.0055 (8)	0.0424 (10)	−0.0120 (8)
O2	0.0567 (9)	0.0472 (8)	0.0682 (10)	−0.0103 (7)	0.0345 (8)	−0.0003 (7)
S1	0.0721 (4)	0.0362 (3)	0.0889 (5)	−0.0085 (3)	0.0561 (4)	−0.0090 (3)

Geometric parameters (Å, º)

C1—C6	1.349 (3)	C10—O1	1.221 (2)
C1—C2	1.502 (3)	C10—N2	1.420 (2)
C1—S1	1.7409 (19)	C11—C12	1.475 (3)
C2—C3	1.523 (3)	C11—C13	1.477 (3)
C2—H2A	0.9700	C11—N2	1.495 (2)
C2—H2B	0.9700	C11—H11	0.9800
C3—C4	1.505 (3)	C12—H12A	0.9600
C3—H3A	0.9700	C12—H12B	0.9600
C3—H3B	0.9700	C12—H12C	0.9600
C4—C5	1.515 (3)	C13—H13A	0.9600
C4—H4A	0.9700	C13—H13B	0.9600
C4—H4B	0.9700	C13—H13C	0.9600
C5—C6	1.509 (3)	C14—O2	1.450 (2)
C5—H5A	0.9700	C14—C15	1.496 (2)
C5—H5B	0.9700	C14—H14A	0.9700
C6—C7	1.437 (3)	C14—H14B	0.9700
C7—C8	1.381 (2)	C15—C16	1.515 (3)
C7—C10	1.432 (3)	C15—H15A	0.9700
C8—N1	1.361 (2)	C15—H15B	0.9700
C8—S1	1.7248 (18)	C16—H16A	0.9600
C9—N1	1.294 (2)	C16—H16B	0.9600
C9—O2	1.330 (2)	C16—H16C	0.9600
C9—N2	1.378 (2)
C6—C1—C2	125.95 (18)	C12—C11—C13	117.7 (2)
C6—C1—S1	112.85 (15)	C12—C11—N2	113.06 (17)
C2—C1—S1	121.20 (15)	C13—C11—N2	113.98 (18)
C1—C2—C3	108.91 (17)	C12—C11—H11	103.3
C1—C2—H2A	109.9	C13—C11—H11	103.3
C3—C2—H2A	109.9	N2—C11—H11	103.3
C1—C2—H2B	109.9	C11—C12—H12A	109.5
C3—C2—H2B	109.9	C11—C12—H12B	109.5
H2A—C2—H2B	108.3	H12A—C12—H12B	109.5
C4—C3—C2	111.09 (18)	C11—C12—H12C	109.5
C4—C3—H3A	109.4	H12A—C12—H12C	109.5
C2—C3—H3A	109.4	H12B—C12—H12C	109.5
C4—C3—H3B	109.4	C11—C13—H13A	109.5
C2—C3—H3B	109.4	C11—C13—H13B	109.5
H3A—C3—H3B	108.0	H13A—C13—H13B	109.5
C3—C4—C5	112.87 (17)	C11—C13—H13C	109.5
C3—C4—H4A	109.0	H13A—C13—H13C	109.5
C5—C4—H4A	109.0	H13B—C13—H13C	109.5
C3—C4—H4B	109.0	O2—C14—C15	107.99 (16)
C5—C4—H4B	109.0	O2—C14—H14A	110.1
H4A—C4—H4B	107.8	C15—C14—H14A	110.1
C6—C5—C4	111.67 (17)	O2—C14—H14B	110.1
C6—C5—H5A	109.3	C15—C14—H14B	110.1
C4—C5—H5A	109.3	H14A—C14—H14B	108.4
C6—C5—H5B	109.3	C14—C15—C16	111.36 (18)
C4—C5—H5B	109.3	C14—C15—H15A	109.4
H5A—C5—H5B	107.9	C16—C15—H15A	109.4
C1—C6—C7	111.73 (17)	C14—C15—H15B	109.4
C1—C6—C5	121.51 (18)	C16—C15—H15B	109.4
C7—C6—C5	126.75 (17)	H15A—C15—H15B	108.0
C8—C7—C10	118.27 (18)	C15—C16—H16A	109.5
C8—C7—C6	112.96 (16)	C15—C16—H16B	109.5
C10—C7—C6	128.77 (18)	H16A—C16—H16B	109.5
N1—C8—C7	126.37 (17)	C15—C16—H16C	109.5
N1—C8—S1	122.33 (14)	H16A—C16—H16C	109.5
C7—C8—S1	111.30 (14)	H16B—C16—H16C	109.5
N1—C9—O2	120.51 (18)	C9—N1—C8	114.38 (16)
N1—C9—N2	125.98 (18)	C9—N2—C10	120.84 (16)
O2—C9—N2	113.51 (16)	C9—N2—C11	122.58 (17)
O1—C10—N2	120.18 (18)	C10—N2—C11	116.57 (16)
O1—C10—C7	125.69 (19)	C9—O2—C14	116.80 (15)
N2—C10—C7	114.14 (17)	C8—S1—C1	91.16 (9)
C6—C1—C2—C3	−17.2 (3)	O2—C9—N1—C8	−179.31 (16)
S1—C1—C2—C3	162.31 (15)	N2—C9—N1—C8	0.9 (3)
C1—C2—C3—C4	47.5 (2)	C7—C8—N1—C9	0.3 (3)
C2—C3—C4—C5	−62.7 (2)	S1—C8—N1—C9	179.65 (15)
C3—C4—C5—C6	41.5 (2)	N1—C9—N2—C10	−0.9 (3)
C2—C1—C6—C7	178.87 (18)	O2—C9—N2—C10	179.24 (15)
S1—C1—C6—C7	−0.7 (2)	N1—C9—N2—C11	−179.47 (19)
C2—C1—C6—C5	−1.8 (3)	O2—C9—N2—C11	0.7 (3)
S1—C1—C6—C5	178.67 (15)	O1—C10—N2—C9	−179.99 (17)
C4—C5—C6—C1	−9.9 (3)	C7—C10—N2—C9	−0.2 (3)
C4—C5—C6—C7	169.28 (18)	O1—C10—N2—C11	−1.4 (3)
C1—C6—C7—C8	1.0 (2)	C7—C10—N2—C11	178.40 (16)
C5—C6—C7—C8	−178.32 (18)	C12—C11—N2—C9	69.8 (3)
C1—C6—C7—C10	−179.07 (18)	C13—C11—N2—C9	−68.1 (3)
C5—C6—C7—C10	1.6 (3)	C12—C11—N2—C10	−108.8 (2)
C10—C7—C8—N1	−1.4 (3)	C13—C11—N2—C10	113.3 (2)
C6—C7—C8—N1	178.57 (17)	N1—C9—O2—C14	−0.9 (3)
C10—C7—C8—S1	179.20 (14)	N2—C9—O2—C14	178.96 (15)
C6—C7—C8—S1	−0.8 (2)	C15—C14—O2—C9	−177.50 (16)
C8—C7—C10—O1	−179.00 (19)	N1—C8—S1—C1	−179.04 (17)
C6—C7—C10—O1	1.0 (3)	C7—C8—S1—C1	0.39 (15)
C8—C7—C10—N2	1.2 (3)	C6—C1—S1—C8	0.17 (16)
C6—C7—C10—N2	−178.73 (17)	C2—C1—S1—C8	−179.38 (17)
O2—C14—C15—C16	178.19 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16C···O1	0.96	2.56	3.520 (3)	175
C11—H11···O1	0.98	2.15	2.717 (3)	115
C12—H12A···O2	0.96	2.54	3.030 (3)	112
C13—H13A···O2	0.96	2.47	3.003 (3)	115