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

Zeng, X.-H.; Ding, M.-W.; He, H.-W.

doi:10.1107/S1600536805042881

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

In the title compound, C₁₉H₂₀N₂O₂S, the central thienopyrimidine ring system is essentially planar. The molecular structure is stabilized by C—H

O hydrogen bonds. In the crystal packing, the molecules are linked only by van der Waals forces.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805042881/rz6162sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805042881/rz6162Isup2.hkl Contains datablock I

CCDC reference: 298528

checkCIF report

Key indicators

Single-crystal X-ray study
T = 292 K
Mean (C-C) = 0.007 Å
Disorder in main residue
R factor = 0.060
wR factor = 0.169
Data-to-parameter ratio = 15.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        C14
PLAT331_ALERT_2_B Small Average Phenyl C-C Dist.   C14    -C19           1.35 Ang.

Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT166_ALERT_4_C S.U's Given on Coordinates for calc-flagged ....        H10
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O2
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C16
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C18
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C17
PLAT301_ALERT_3_C Main Residue  Disorder .........................       8.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           26.99
           From the CIF: _reflns_number_total               3473
           Count of symmetry unique reflns         2110
           Completeness (_total/calc)            164.60%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1363
           Fraction of Friedel pairs measured     0.646
           Are heavy atom types Z>Si present        yes

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

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

Computing details top

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 (Sheldrick, 2001).

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

Crystal data top

C₁₉H₂₀N₂O₂S	F(000) = 360
M_r = 340.43	D_x = 1.290 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1462 reflections
a = 12.4411 (15) Å	θ = 2.9–21.1°
b = 5.8030 (7) Å	µ = 0.20 mm⁻¹
c = 13.2870 (16) Å	T = 292 K
β = 113.994 (2)°	Block, colourless
V = 876.37 (18) Å³	0.30 × 0.20 × 0.20 mm
Z = 2

Data collection top

Bruker SMART CCD area-detector diffractometer	3473 independent reflections
Radiation source: fine-focus sealed tube	2596 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
φ and ω scans	θ_max = 27.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→15
T_min = 0.943, T_max = 0.962	k = −7→7
5473 measured reflections	l = −16→16

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)] = 0.060	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.169	w = 1/[σ²(F_o²) + (0.0921P)²] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
3473 reflections	Δρ_max = 0.27 e Å⁻³
231 parameters	Δρ_min = −0.23 e Å⁻³
7 restraints	Absolute structure: Flack (1983), 1386 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.01 (12)

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	0.9240 (3)	0.4842 (8)	0.1298 (3)	0.0669 (11)
H1A	0.9802	0.4889	0.2061	0.080*	0.690 (12)
H1B	0.9416	0.6114	0.0916	0.080*	0.690 (12)
H1C	0.9730	0.4045	0.1971	0.080*	0.310 (12)
H1D	0.9593	0.6332	0.1295	0.080*	0.310 (12)
C2	0.9384 (5)	0.2595 (13)	0.0786 (6)	0.074 (2)	0.690 (12)
H2A	1.0100	0.2647	0.0662	0.089*	0.690 (12)
H2B	0.9453	0.1335	0.1289	0.089*	0.690 (12)
C3	0.8349 (5)	0.2174 (19)	−0.0290 (5)	0.086 (3)	0.690 (12)
H3A	0.8485	0.0768	−0.0616	0.103*	0.690 (12)
H3B	0.8294	0.3431	−0.0790	0.103*	0.690 (12)
C2'	0.9153 (14)	0.340 (2)	0.0304 (11)	0.058 (4)*	0.310 (12)
H2C	0.8792	0.4321	−0.0358	0.070*	0.310 (12)
H2D	0.9941	0.2999	0.0383	0.070*	0.310 (12)
C3'	0.8446 (7)	0.1200 (19)	0.0167 (14)	0.062 (4)*	0.310 (12)
H3C	0.8521	0.0222	−0.0393	0.075*	0.310 (12)
H3D	0.8716	0.0351	0.0855	0.075*	0.310 (12)
C4	0.7182 (3)	0.1966 (9)	−0.0177 (3)	0.0735 (12)
H4A	0.6535	0.2154	−0.0892	0.088*	0.690 (12)
H4B	0.7119	0.0451	0.0103	0.088*	0.690 (12)
H4C	0.6814	0.2534	−0.0927	0.088*	0.310 (12)
H4D	0.6739	0.0633	−0.0121	0.088*	0.310 (12)
C5	0.7116 (3)	0.3772 (7)	0.0593 (3)	0.0565 (9)
C6	0.8021 (3)	0.5150 (7)	0.1251 (2)	0.0522 (9)
C7	0.7671 (3)	0.6691 (7)	0.1887 (3)	0.0529 (8)
C8	0.6489 (3)	0.6475 (7)	0.1689 (3)	0.0559 (9)
C9	0.8379 (3)	0.8259 (6)	0.2744 (3)	0.0527 (8)
C10	0.8484 (3)	1.0705 (6)	0.4318 (3)	0.0560 (9)
H10	0.929 (3)	1.064 (8)	0.438 (3)	0.067*
C11	0.8170 (5)	1.3217 (8)	0.4244 (4)	0.0845 (14)
H11A	0.8206	1.3866	0.3594	0.127*
H11B	0.8716	1.4005	0.4883	0.127*
H11C	0.7388	1.3385	0.4209	0.127*
C12	0.8509 (4)	0.9572 (8)	0.5348 (3)	0.0738 (11)
H12A	0.7727	0.9523	0.5321	0.111*
H12B	0.9009	1.0438	0.5980	0.111*
H12C	0.8807	0.8031	0.5397	0.111*
C13	0.6584 (3)	0.9013 (7)	0.2978 (3)	0.0585 (9)
C14	0.4938 (3)	1.0177 (7)	0.3327 (3)	0.0610 (10)
C15	0.4558 (5)	0.8412 (10)	0.3764 (5)	0.1005 (17)
H15	0.5069	0.7245	0.4157	0.121*
C16	0.3396 (7)	0.8388 (15)	0.3613 (6)	0.130 (2)
H16	0.3103	0.7162	0.3875	0.155*
C17	0.2672 (5)	1.0180 (15)	0.3073 (6)	0.110 (2)
H17	0.1894	1.0190	0.2994	0.132*
C18	0.3059 (5)	1.1848 (16)	0.2674 (5)	0.127 (2)
H18	0.2559	1.3053	0.2311	0.152*
C19	0.4225 (4)	1.1865 (12)	0.2781 (4)	0.0995 (16)
H19	0.4495	1.3049	0.2473	0.119*
N1	0.7763 (2)	0.9347 (6)	0.3305 (2)	0.0543 (7)
N2	0.5916 (2)	0.7707 (6)	0.2201 (2)	0.0606 (8)
O1	0.9429 (2)	0.8604 (5)	0.3023 (2)	0.0682 (8)
O2	0.6138 (2)	1.0358 (6)	0.3550 (2)	0.0793 (9)
S1	0.58093 (8)	0.44030 (19)	0.07274 (8)	0.0693 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.055 (2)	0.091 (3)	0.063 (2)	−0.003 (2)	0.0315 (17)	−0.008 (2)
C2	0.064 (4)	0.088 (5)	0.074 (4)	0.013 (4)	0.031 (3)	0.004 (4)
C3	0.079 (4)	0.120 (7)	0.064 (4)	0.030 (4)	0.034 (3)	−0.005 (5)
C4	0.069 (2)	0.087 (3)	0.064 (2)	0.013 (2)	0.0251 (19)	−0.008 (2)
C5	0.0524 (18)	0.065 (2)	0.0488 (16)	0.0058 (17)	0.0174 (15)	−0.0023 (17)
C6	0.0507 (18)	0.064 (2)	0.0417 (16)	0.0041 (17)	0.0186 (14)	0.0066 (15)
C7	0.0489 (18)	0.068 (2)	0.0434 (16)	−0.0004 (17)	0.0205 (14)	0.0070 (16)
C8	0.0478 (19)	0.064 (2)	0.0509 (18)	0.0075 (18)	0.0151 (15)	0.0003 (17)
C9	0.051 (2)	0.055 (2)	0.0481 (17)	−0.0043 (16)	0.0160 (16)	0.0043 (16)
C10	0.060 (2)	0.0412 (19)	0.059 (2)	−0.0026 (17)	0.0155 (17)	−0.0057 (16)
C11	0.100 (3)	0.044 (2)	0.089 (3)	−0.005 (2)	0.018 (2)	0.007 (2)
C12	0.098 (3)	0.060 (2)	0.057 (2)	0.008 (3)	0.0236 (19)	0.002 (2)
C13	0.0529 (19)	0.067 (3)	0.0564 (18)	0.0003 (19)	0.0228 (16)	−0.0070 (19)
C14	0.061 (2)	0.065 (3)	0.063 (2)	0.0030 (19)	0.0305 (18)	−0.0111 (19)
C15	0.102 (4)	0.084 (4)	0.123 (4)	0.002 (3)	0.054 (3)	0.018 (3)
C16	0.146 (6)	0.133 (6)	0.157 (6)	−0.040 (5)	0.110 (5)	−0.016 (5)
C17	0.083 (4)	0.142 (6)	0.128 (5)	−0.015 (4)	0.065 (4)	−0.048 (5)
C18	0.084 (4)	0.154 (7)	0.124 (5)	0.039 (5)	0.023 (4)	0.012 (5)
C19	0.084 (3)	0.113 (4)	0.102 (4)	0.010 (3)	0.038 (3)	0.027 (4)
N1	0.0518 (15)	0.0629 (18)	0.0476 (13)	−0.0032 (16)	0.0196 (12)	−0.0024 (14)
N2	0.0499 (17)	0.063 (2)	0.0667 (18)	−0.0002 (15)	0.0216 (14)	−0.0184 (16)
O1	0.0508 (14)	0.085 (2)	0.0686 (15)	−0.0102 (13)	0.0241 (12)	−0.0083 (14)
O2	0.0617 (16)	0.088 (2)	0.0918 (19)	−0.0028 (15)	0.0349 (14)	−0.0397 (17)
S1	0.0479 (5)	0.0818 (7)	0.0712 (6)	−0.0003 (5)	0.0172 (4)	−0.0232 (5)

Geometric parameters (Å, º) top

C1—C6	1.503 (5)	C8—N2	1.370 (4)
C1—C2	1.515 (6)	C8—S1	1.707 (4)
C1—C2'	1.531 (8)	C9—O1	1.220 (4)
C1—H1A	0.9700	C9—N1	1.416 (4)
C1—H1B	0.9700	C10—C11	1.502 (6)
C1—H1C	0.9700	C10—N1	1.502 (4)
C1—H1D	0.9700	C10—C12	1.507 (5)
C2—C3	1.505 (7)	C10—H10	0.98 (4)
C2—H2A	0.9700	C11—H11A	0.9600
C2—H2B	0.9700	C11—H11B	0.9600
C3—C4	1.524 (6)	C11—H11C	0.9600
C3—H3A	0.9700	C12—H12A	0.9600
C3—H3B	0.9700	C12—H12B	0.9600
C2'—C3'	1.517 (9)	C12—H12C	0.9600
C2'—H2C	0.9700	C13—N2	1.278 (4)
C2'—H2D	0.9700	C13—O2	1.356 (4)
C3'—C4	1.515 (8)	C13—N1	1.364 (4)
C3'—H3C	0.9700	C14—C19	1.323 (7)
C3'—H3D	0.9700	C14—C15	1.354 (7)
C4—C5	1.490 (6)	C14—O2	1.402 (4)
C4—H4A	0.9700	C15—C16	1.376 (9)
C4—H4B	0.9700	C15—H15	0.9300
C4—H4C	0.9700	C16—C17	1.372 (10)
C4—H4D	0.9700	C16—H16	0.9300
C5—C6	1.367 (5)	C17—C18	1.287 (9)
C5—S1	1.745 (4)	C17—H17	0.9300
C6—C7	1.415 (5)	C18—C19	1.398 (8)
C7—C8	1.391 (4)	C18—H18	0.9300
C7—C9	1.444 (5)	C19—H19	0.9300

C6—C1—C2	112.6 (4)	C6—C5—C4	126.1 (3)
C6—C1—C2'	108.2 (6)	C6—C5—S1	111.8 (3)
C6—C1—H1A	109.1	C4—C5—S1	122.1 (3)
C2—C1—H1A	109.1	C5—C6—C7	112.2 (3)
C2'—C1—H1A	133.2	C5—C6—C1	120.8 (3)
C6—C1—H1B	109.1	C7—C6—C1	126.9 (3)
C2—C1—H1B	109.1	C8—C7—C6	112.9 (3)
C2'—C1—H1B	85.2	C8—C7—C9	117.8 (3)
H1A—C1—H1B	107.8	C6—C7—C9	129.2 (3)
C6—C1—H1C	109.9	N2—C8—C7	125.7 (3)
C2—C1—H1C	81.9	N2—C8—S1	122.7 (3)
C2'—C1—H1C	109.4	C7—C8—S1	111.6 (3)
H1B—C1—H1C	130.9	O1—C9—N1	120.5 (3)
C6—C1—H1D	110.2	O1—C9—C7	125.3 (3)
C2—C1—H1D	129.0	N1—C9—C7	114.1 (3)
C2'—C1—H1D	111.0	C11—C10—N1	114.0 (3)
H1A—C1—H1D	81.1	C11—C10—C12	113.1 (4)
H1C—C1—H1D	108.3	N1—C10—C12	111.7 (3)
C3—C2—C1	110.8 (6)	C11—C10—H10	106 (3)
C3—C2—H2A	109.5	N1—C10—H10	106 (2)
C1—C2—H2A	109.5	C12—C10—H10	106 (2)
C3—C2—H2B	109.5	C10—C11—H11A	109.5
C1—C2—H2B	109.5	C10—C11—H11B	109.5
H2A—C2—H2B	108.1	H11A—C11—H11B	109.5
C2—C3—C4	113.6 (5)	C10—C11—H11C	109.5
C2—C3—H3A	108.8	H11A—C11—H11C	109.5
C4—C3—H3A	108.8	H11B—C11—H11C	109.5
C2—C3—H3B	108.8	C10—C12—H12A	109.5
C4—C3—H3B	108.8	C10—C12—H12B	109.5
H3A—C3—H3B	107.7	H12A—C12—H12B	109.5
C3'—C2'—C1	113.5 (10)	C10—C12—H12C	109.5
C3'—C2'—H2C	108.9	H12A—C12—H12C	109.5
C1—C2'—H2C	108.9	H12B—C12—H12C	109.5
C3'—C2'—H2D	108.9	N2—C13—O2	120.9 (3)
C1—C2'—H2D	108.9	N2—C13—N1	127.2 (3)
H2C—C2'—H2D	107.7	O2—C13—N1	111.8 (3)
C4—C3'—C2'	105.6 (9)	C19—C14—C15	121.4 (4)
C4—C3'—H3C	110.6	C19—C14—O2	118.7 (4)
C2'—C3'—H3C	110.6	C15—C14—O2	119.6 (4)
C4—C3'—H3D	110.6	C14—C15—C16	118.3 (6)
C2'—C3'—H3D	110.6	C14—C15—H15	120.8
H3C—C3'—H3D	108.7	C16—C15—H15	120.8
C5—C4—C3'	109.9 (6)	C17—C16—C15	119.7 (6)
C5—C4—C3	109.4 (4)	C17—C16—H16	120.1
C5—C4—H4A	109.8	C15—C16—H16	120.1
C3'—C4—H4A	132.4	C18—C17—C16	120.6 (6)
C3—C4—H4A	109.8	C18—C17—H17	119.7
C5—C4—H4B	109.8	C16—C17—H17	119.7
C3'—C4—H4B	81.6	C17—C18—C19	120.6 (6)
C3—C4—H4B	109.8	C17—C18—H18	119.7
H4A—C4—H4B	108.2	C19—C18—H18	119.7
C5—C4—H4C	109.4	C14—C19—C18	119.2 (6)
C3'—C4—H4C	114.1	C14—C19—H19	120.4
C3—C4—H4C	86.7	C18—C19—H19	120.4
H4B—C4—H4C	128.6	C13—N1—C9	120.7 (3)
C5—C4—H4D	108.4	C13—N1—C10	122.2 (3)
C3'—C4—H4D	107.2	C9—N1—C10	116.9 (3)
C3—C4—H4D	131.6	C13—N2—C8	114.3 (3)
H4A—C4—H4D	83.9	C13—O2—C14	118.8 (3)
H4C—C4—H4D	107.7	C8—S1—C5	91.48 (17)

C6—C1—C2—C3	44.5 (8)	C6—C7—C9—N1	−172.6 (3)
C2'—C1—C2—C3	−42.2 (10)	C19—C14—C15—C16	1.1 (8)
C1—C2—C3—C4	−61.5 (11)	O2—C14—C15—C16	174.3 (5)
C6—C1—C2'—C3'	−50.4 (14)	C14—C15—C16—C17	−2.9 (9)
C2—C1—C2'—C3'	53.7 (9)	C15—C16—C17—C18	2.3 (11)
C1—C2'—C3'—C4	69.6 (17)	C16—C17—C18—C19	0.1 (11)
C2'—C3'—C4—C5	−50.7 (13)	C15—C14—C19—C18	1.3 (8)
C2'—C3'—C4—C3	44.2 (8)	O2—C14—C19—C18	−172.0 (5)
C2—C3—C4—C5	42.7 (10)	C17—C18—C19—C14	−1.9 (10)
C2—C3—C4—C3'	−53.7 (10)	N2—C13—N1—C9	2.5 (6)
C3'—C4—C5—C6	21.9 (8)	O2—C13—N1—C9	−174.4 (3)
C3—C4—C5—C6	−10.6 (6)	N2—C13—N1—C10	−172.4 (4)
C3'—C4—C5—S1	−159.5 (6)	O2—C13—N1—C10	10.7 (5)
C3—C4—C5—S1	167.9 (4)	O1—C9—N1—C13	178.3 (3)
C4—C5—C6—C7	−180.0 (4)	C7—C9—N1—C13	−4.5 (5)
S1—C5—C6—C7	1.4 (4)	O1—C9—N1—C10	−6.5 (5)
C4—C5—C6—C1	−3.7 (6)	C7—C9—N1—C10	170.6 (3)
S1—C5—C6—C1	177.7 (3)	C11—C10—N1—C13	−65.8 (5)
C2—C1—C6—C5	−13.7 (6)	C12—C10—N1—C13	63.8 (5)
C2'—C1—C6—C5	16.4 (7)	C11—C10—N1—C9	119.1 (4)
C2—C1—C6—C7	162.1 (5)	C12—C10—N1—C9	−111.2 (4)
C2'—C1—C6—C7	−167.9 (7)	O2—C13—N2—C8	179.2 (3)
C5—C6—C7—C8	−0.8 (4)	N1—C13—N2—C8	2.6 (6)
C1—C6—C7—C8	−176.8 (3)	C7—C8—N2—C13	−5.6 (6)
C5—C6—C7—C9	173.8 (3)	S1—C8—N2—C13	173.1 (3)
C1—C6—C7—C9	−2.2 (6)	N2—C13—O2—C14	4.3 (6)
C6—C7—C8—N2	178.6 (3)	N1—C13—O2—C14	−178.6 (3)
C9—C7—C8—N2	3.4 (6)	C19—C14—O2—C13	−107.0 (5)
C6—C7—C8—S1	−0.2 (4)	C15—C14—O2—C13	79.6 (5)
C9—C7—C8—S1	−175.4 (3)	N2—C8—S1—C5	−178.0 (3)
C8—C7—C9—O1	178.8 (4)	C7—C8—S1—C5	0.8 (3)
C6—C7—C9—O1	4.4 (6)	C6—C5—S1—C8	−1.2 (3)
C8—C7—C9—N1	1.8 (5)	C4—C5—S1—C8	−180.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O1	0.98 (4)	2.21 (4)	2.733 (5)	112 (3)
C11—H11C···O2	0.96	2.27	2.846 (6)	118
C12—H12A···O2	0.96	2.43	2.981 (5)	116

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

Supporting information

Key indicators

checkCIF/PLATON results

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