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The molecule of the title compound, C15H16N2O2S, has crystallographic mirror symmetry. The crystal structure is stabilized by inter- and intra­molecular C—H...O hydrogen-bonding inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805024177/at6024sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805024177/at6024Isup2.hkl
Contains datablock I

CCDC reference: 283743

Key indicators

  • Single-crystal X-ray study
  • T = 292 K
  • Mean [sigma](C-C)= 0.003 Å
  • R factor = 0.044
  • wR factor = 0.122
  • Data-to-parameter ratio = 14.7

checkCIF/PLATON results

No syntax errors found


No errors found in this datablock

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: SHELXTL (Sheldrick, 2001); software used to prepare material for publication: SHELXTL.

2-Ethoxy-3-isopropylbenzo[4,5]thieno[3,2-d]pyrimidin-4(3H)-one top
Crystal data top
C15H16N2O2SDx = 1.339 Mg m3
Mr = 288.36Melting point: 439 K
Orthorhombic, PnmaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2nCell parameters from 1811 reflections
a = 13.3930 (16) Åθ = 2.6–24.4°
b = 6.8922 (8) ŵ = 0.23 mm1
c = 15.4970 (18) ÅT = 292 K
V = 1430.5 (3) Å3Block, colorless
Z = 40.30 × 0.20 × 0.20 mm
F(000) = 608
Data collection top
Bruker SMART 4K CCD area-detector
diffractometer
1339 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.039
Graphite monochromatorθmax = 27.5°, θmin = 2.0°
φ and ω scansh = 1716
8299 measured reflectionsk = 88
1768 independent reflectionsl = 2015
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0653P)2 + 0.1581P]
where P = (Fo2 + 2Fc2)/3
1768 reflections(Δ/σ)max < 0.001
120 parametersΔρmax = 0.29 e Å3
0 restraintsΔρmin = 0.24 e Å3
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
xyzUiso*/UeqOcc. (<1)
C10.49801 (18)0.25000.36424 (14)0.0429 (5)
C20.4099 (2)0.25000.31674 (15)0.0513 (6)
H20.41130.25000.25670.062*
C30.32083 (19)0.25000.36069 (17)0.0527 (6)
H30.26120.25000.32990.063*
C40.31837 (18)0.25000.45112 (16)0.0521 (6)
H40.25720.25000.47960.063*
C50.40519 (16)0.25000.49810 (15)0.0442 (5)
H50.40330.25000.55810.053*
C60.49593 (16)0.25000.45486 (13)0.0379 (5)
C70.59575 (15)0.25000.49016 (13)0.0365 (5)
C80.66755 (17)0.25000.42693 (13)0.0421 (5)
C90.77150 (17)0.25000.44766 (14)0.0451 (6)
C100.71121 (15)0.25000.59498 (13)0.0375 (5)
C110.66507 (18)0.25000.74256 (14)0.0473 (6)
H11A0.62330.13570.73700.057*0.50
H11B0.62330.36430.73700.057*0.50
C120.7166 (2)0.25000.82715 (15)0.0608 (7)
H12A0.76970.15640.82630.091*0.50
H12B0.66990.21700.87180.091*0.50
H12C0.74370.37660.83820.091*0.50
C130.89701 (16)0.25000.56478 (16)0.0486 (6)
H130.93620.25000.51140.058*
C140.92519 (14)0.0658 (3)0.61179 (14)0.0714 (6)
H14A0.89290.06320.66710.107*
H14B0.99630.06170.61960.107*
H14C0.90430.04450.57850.107*
N10.78992 (13)0.25000.53721 (11)0.0402 (4)
N20.61726 (12)0.25000.57616 (11)0.0373 (4)
O10.84015 (13)0.25000.39468 (11)0.0659 (6)
O20.74189 (11)0.25000.67665 (9)0.0469 (4)
S10.61938 (5)0.25000.32309 (4)0.0538 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0495 (13)0.0451 (13)0.0341 (12)0.0000.0038 (9)0.000
C20.0640 (16)0.0505 (15)0.0394 (12)0.0000.0153 (11)0.000
C30.0470 (14)0.0560 (15)0.0551 (15)0.0000.0188 (11)0.000
C40.0387 (13)0.0621 (16)0.0555 (16)0.0000.0055 (10)0.000
C50.0393 (12)0.0536 (14)0.0396 (12)0.0000.0018 (9)0.000
C60.0411 (12)0.0408 (12)0.0317 (11)0.0000.0025 (8)0.000
C70.0379 (11)0.0398 (12)0.0317 (10)0.0000.0005 (8)0.000
C80.0455 (13)0.0517 (14)0.0291 (10)0.0000.0014 (9)0.000
C90.0430 (13)0.0562 (15)0.0362 (12)0.0000.0066 (9)0.000
C100.0340 (11)0.0446 (12)0.0340 (11)0.0000.0009 (8)0.000
C110.0441 (13)0.0637 (15)0.0342 (11)0.0000.0018 (9)0.000
C120.0571 (16)0.088 (2)0.0374 (13)0.0000.0039 (11)0.000
C130.0332 (12)0.0647 (16)0.0478 (13)0.0000.0020 (9)0.000
C140.0468 (11)0.0737 (14)0.0935 (16)0.0111 (10)0.0056 (10)0.0133 (12)
N10.0329 (9)0.0518 (11)0.0360 (10)0.0000.0012 (7)0.000
N20.0338 (9)0.0491 (11)0.0290 (9)0.0000.0004 (7)0.000
O10.0467 (10)0.1082 (16)0.0427 (9)0.0000.0135 (8)0.000
O20.0365 (8)0.0728 (11)0.0315 (8)0.0000.0025 (6)0.000
S10.0541 (4)0.0785 (5)0.0288 (3)0.0000.0015 (2)0.000
Geometric parameters (Å, º) top
C1—C21.390 (3)C10—N21.292 (3)
C1—C61.405 (3)C10—O21.331 (2)
C1—S11.746 (2)C10—N11.383 (3)
C2—C31.374 (4)C11—O21.450 (3)
C2—H20.9300C11—C121.482 (3)
C3—C41.402 (4)C11—H11A0.9700
C3—H30.9300C11—H11B0.9700
C4—C51.372 (3)C12—H12A0.9600
C4—H40.9300C12—H12B0.9600
C5—C61.388 (3)C12—H12C0.9600
C5—H50.9300C13—N11.496 (3)
C6—C71.444 (3)C13—C141.512 (2)
C7—N21.364 (3)C13—C14i1.512 (2)
C7—C81.373 (3)C13—H130.9800
C8—C91.429 (3)C14—H14A0.9600
C8—S11.734 (2)C14—H14B0.9600
C9—O11.233 (3)C14—H14C0.9600
C9—N11.409 (3)
C2—C1—C6120.8 (2)O2—C11—C12107.01 (19)
C2—C1—S1126.61 (18)O2—C11—H11A110.3
C6—C1—S1112.56 (17)C12—C11—H11A110.3
C3—C2—C1118.3 (2)O2—C11—H11B110.3
C3—C2—H2120.8C12—C11—H11B110.3
C1—C2—H2120.8H11A—C11—H11B108.6
C2—C3—C4121.1 (2)C11—C12—H12A109.5
C2—C3—H3119.5C11—C12—H12B109.5
C4—C3—H3119.5H12A—C12—H12B109.5
C5—C4—C3120.7 (2)C11—C12—H12C109.5
C5—C4—H4119.6H12A—C12—H12C109.5
C3—C4—H4119.6H12B—C12—H12C109.5
C4—C5—C6119.1 (2)N1—C13—C14112.14 (13)
C4—C5—H5120.5N1—C13—C14i112.14 (13)
C6—C5—H5120.5C14—C13—C14i114.3 (2)
C5—C6—C1120.0 (2)N1—C13—H13105.8
C5—C6—C7128.88 (19)C14—C13—H13105.8
C1—C6—C7111.11 (19)C14i—C13—H13105.8
N2—C7—C8123.34 (19)C13—C14—H14A109.5
N2—C7—C6124.45 (18)C13—C14—H14B109.5
C8—C7—C6112.21 (19)H14A—C14—H14B109.5
C7—C8—C9121.5 (2)C13—C14—H14C109.5
C7—C8—S1113.69 (17)H14A—C14—H14C109.5
C9—C8—S1124.85 (17)H14B—C14—H14C109.5
O1—C9—N1121.7 (2)C10—N1—C9120.26 (18)
O1—C9—C8125.2 (2)C10—N1—C13123.07 (18)
N1—C9—C8113.08 (18)C9—N1—C13116.67 (18)
N2—C10—O2121.04 (19)C10—N2—C7115.25 (18)
N2—C10—N1126.60 (19)C10—O2—C11116.80 (17)
O2—C10—N1112.35 (18)C8—S1—C190.43 (11)
C6—C1—C2—C30.0N2—C10—N1—C90.0
S1—C1—C2—C3180.0O2—C10—N1—C9180.0
C1—C2—C3—C40.0N2—C10—N1—C13180.0
C2—C3—C4—C50.0O2—C10—N1—C130.0
C3—C4—C5—C60.0O1—C9—N1—C10180.0
C4—C5—C6—C10.0C8—C9—N1—C100.0
C4—C5—C6—C7180.0O1—C9—N1—C130.0
C2—C1—C6—C50.0C8—C9—N1—C13180.0
S1—C1—C6—C5180.0C14—C13—N1—C1065.06 (16)
C2—C1—C6—C7180.0C14i—C13—N1—C1065.06 (16)
S1—C1—C6—C70.0C14—C13—N1—C9114.94 (16)
C5—C6—C7—N20.0C14i—C13—N1—C9114.94 (16)
C1—C6—C7—N2180.0O2—C10—N2—C7180.0
C5—C6—C7—C8180.0N1—C10—N2—C70.0
C1—C6—C7—C80.0C8—C7—N2—C100.0
N2—C7—C8—C90.0C6—C7—N2—C10180.0
C6—C7—C8—C9180.0N2—C10—O2—C110.0
N2—C7—C8—S1180.0N1—C10—O2—C11180.0
C6—C7—C8—S10.0C12—C11—O2—C10180.0
C7—C8—C9—O1180.0C7—C8—S1—C10.0
S1—C8—C9—O10.0C9—C8—S1—C1180.0
C7—C8—C9—N10.0C2—C1—S1—C8180.0
S1—C8—C9—N1180.0C6—C1—S1—C80.0
Symmetry code: (i) x, y+1/2, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C14—H14A···O20.962.402.941 (2)115
C13—H13···O10.982.222.744 (3)112
C2—H2···O1ii0.932.533.407 (3)157
Symmetry code: (ii) x1/2, y+1/2, z+1/2.
 

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