Download citation
Download citation
link to html
In the crystal structure of the title compound, C18H14N2O2S, the packing of the mol­ecules is mainly governed by inter­molecular π–π inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806015959/is2030sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806015959/is2030Isup2.hkl
Contains datablock I

CCDC reference: 610815

Key indicators

  • Single-crystal X-ray study
  • T = 292 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.045
  • wR factor = 0.120
  • Data-to-parameter ratio = 17.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 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 1 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).

2-Ethoxy-3-phenyl-1-benzothieno[3,2-d]pyrimidin-4(3H)-one top
Crystal data top
C18H14N2O2SDx = 1.412 Mg m3
Mr = 322.37Melting point: 463 K
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 22.4877 (18) ÅCell parameters from 7441 reflections
b = 11.2298 (9) Åθ = 2.3–28.3°
c = 14.8969 (12) ŵ = 0.23 mm1
β = 126.298 (1)°T = 292 K
V = 3031.9 (4) Å3Block, colorless
Z = 80.30 × 0.20 × 0.20 mm
F(000) = 1344
Data collection top
Bruker SMART 4K CCD area-detector
diffractometer
3620 independent reflections
Radiation source: fine-focus sealed tube3090 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.057
φ and ω scansθmax = 28.0°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
h = 2928
Tmin = 0.936, Tmax = 0.956k = 1414
16980 measured reflectionsl = 1919
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)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0671P)2 + 0.7743P]
where P = (Fo2 + 2Fc2)/3
3620 reflections(Δ/σ)max < 0.001
209 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = 0.35 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*/Ueq
C10.02951 (7)0.00160 (12)0.08998 (11)0.0408 (3)
C20.07988 (8)0.09192 (15)0.04456 (12)0.0494 (3)
H20.06450.16930.07040.059*
C30.15289 (9)0.06803 (18)0.03936 (14)0.0594 (4)
H30.18700.12990.07130.071*
C40.17585 (8)0.04851 (18)0.07664 (13)0.0596 (4)
H40.22540.06310.13270.071*
C50.12722 (9)0.14225 (16)0.03289 (13)0.0546 (4)
H50.14330.21950.05830.066*
C60.05263 (8)0.11815 (13)0.05129 (11)0.0454 (3)
C70.04878 (7)0.00306 (12)0.17617 (10)0.0380 (3)
C80.08178 (8)0.10584 (12)0.19779 (11)0.0423 (3)
C90.15982 (8)0.12020 (12)0.27669 (11)0.0439 (3)
C100.15544 (7)0.09391 (11)0.30399 (10)0.0373 (3)
C110.27430 (7)0.01167 (12)0.41539 (11)0.0403 (3)
C120.31985 (8)0.05726 (13)0.40266 (12)0.0481 (3)
H120.30010.10360.33920.058*
C130.39512 (9)0.05632 (16)0.48557 (15)0.0597 (4)
H130.42610.10320.47830.072*
C140.42440 (9)0.01378 (16)0.57889 (15)0.0638 (5)
H140.47510.01450.63400.077*
C150.37891 (9)0.08225 (14)0.59035 (13)0.0592 (4)
H150.39890.12930.65350.071*
C160.30339 (8)0.08216 (12)0.50884 (12)0.0469 (3)
H160.27260.12890.51680.056*
C170.15953 (8)0.29895 (11)0.34532 (12)0.0449 (3)
H17A0.19010.35050.40940.054*
H17B0.11370.28500.33640.054*
C180.14303 (10)0.36009 (14)0.24347 (14)0.0582 (4)
H18A0.18590.35770.24400.087*
H18B0.12980.44150.24300.087*
H18C0.10290.32030.17820.087*
N10.08543 (6)0.10562 (10)0.22964 (9)0.0393 (3)
N20.19518 (6)0.01064 (9)0.33058 (9)0.0394 (3)
O10.19509 (6)0.21130 (9)0.29867 (10)0.0609 (3)
O20.19736 (5)0.18566 (8)0.36566 (8)0.0446 (2)
S10.02024 (2)0.21962 (3)0.11776 (3)0.05381 (15)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0359 (7)0.0508 (8)0.0362 (6)0.0060 (5)0.0216 (6)0.0048 (5)
C20.0402 (7)0.0582 (9)0.0459 (7)0.0015 (6)0.0233 (6)0.0045 (6)
C30.0397 (8)0.0809 (12)0.0494 (8)0.0030 (8)0.0219 (7)0.0017 (8)
C40.0369 (7)0.0915 (13)0.0426 (8)0.0121 (8)0.0194 (6)0.0053 (8)
C50.0489 (8)0.0674 (10)0.0450 (8)0.0222 (7)0.0263 (7)0.0120 (7)
C60.0433 (7)0.0516 (8)0.0416 (7)0.0096 (6)0.0253 (6)0.0048 (6)
C70.0376 (7)0.0394 (7)0.0371 (6)0.0032 (5)0.0221 (6)0.0034 (5)
C80.0412 (7)0.0367 (7)0.0439 (7)0.0071 (5)0.0223 (6)0.0058 (5)
C90.0448 (7)0.0341 (6)0.0469 (7)0.0008 (5)0.0238 (6)0.0027 (5)
C100.0385 (6)0.0339 (6)0.0353 (6)0.0007 (5)0.0197 (5)0.0032 (5)
C110.0362 (7)0.0373 (6)0.0395 (7)0.0028 (5)0.0181 (6)0.0056 (5)
C120.0463 (8)0.0479 (8)0.0483 (8)0.0014 (6)0.0270 (7)0.0047 (6)
C130.0438 (8)0.0603 (10)0.0715 (11)0.0075 (7)0.0322 (8)0.0165 (8)
C140.0382 (8)0.0599 (10)0.0639 (10)0.0087 (7)0.0141 (7)0.0119 (8)
C150.0545 (9)0.0483 (8)0.0473 (8)0.0158 (7)0.0151 (7)0.0013 (6)
C160.0483 (8)0.0389 (7)0.0468 (7)0.0061 (6)0.0245 (6)0.0005 (6)
C170.0453 (7)0.0324 (6)0.0462 (7)0.0003 (5)0.0212 (6)0.0078 (5)
C180.0619 (10)0.0451 (8)0.0564 (9)0.0011 (7)0.0289 (8)0.0025 (7)
N10.0358 (6)0.0370 (6)0.0376 (5)0.0006 (4)0.0176 (5)0.0045 (4)
N20.0356 (6)0.0343 (5)0.0387 (6)0.0004 (4)0.0168 (5)0.0028 (4)
O10.0542 (7)0.0362 (5)0.0683 (7)0.0055 (4)0.0232 (6)0.0060 (5)
O20.0375 (5)0.0350 (5)0.0430 (5)0.0003 (4)0.0139 (4)0.0076 (4)
S10.0505 (2)0.0386 (2)0.0600 (3)0.01165 (14)0.0259 (2)0.00964 (15)
Geometric parameters (Å, º) top
C1—C21.392 (2)C10—N21.3838 (16)
C1—C61.400 (2)C11—C121.384 (2)
C1—C71.4403 (18)C11—C161.384 (2)
C2—C31.379 (2)C11—N21.4493 (17)
C2—H20.9300C12—C131.384 (2)
C3—C41.396 (3)C12—H120.9300
C3—H30.9300C13—C141.379 (3)
C4—C51.373 (2)C13—H130.9300
C4—H40.9300C14—C151.369 (3)
C5—C61.4033 (19)C14—H140.9300
C5—H50.9300C15—C161.385 (2)
C6—S11.7444 (16)C15—H150.9300
C7—N11.3650 (16)C16—H160.9300
C7—C81.3664 (19)C17—O21.4591 (15)
C8—C91.4301 (19)C17—C181.498 (2)
C8—S11.7366 (13)C17—H17A0.9700
C9—O11.2147 (17)C17—H17B0.9700
C9—N21.4265 (17)C18—H18A0.9600
C10—N11.2876 (16)C18—H18B0.9600
C10—O21.3300 (15)C18—H18C0.9600
C2—C1—C6120.55 (13)C11—C12—C13119.14 (15)
C2—C1—C7128.29 (13)C11—C12—H12120.4
C6—C1—C7111.15 (12)C13—C12—H12120.4
C3—C2—C1118.93 (15)C14—C13—C12120.38 (16)
C3—C2—H2120.5C14—C13—H13119.8
C1—C2—H2120.5C12—C13—H13119.8
C2—C3—C4120.31 (16)C15—C14—C13120.02 (15)
C2—C3—H3119.8C15—C14—H14120.0
C4—C3—H3119.8C13—C14—H14120.0
C5—C4—C3121.81 (14)C14—C15—C16120.63 (15)
C5—C4—H4119.1C14—C15—H15119.7
C3—C4—H4119.1C16—C15—H15119.7
C4—C5—C6118.11 (15)C11—C16—C15119.12 (15)
C4—C5—H5120.9C11—C16—H16120.4
C6—C5—H5120.9C15—C16—H16120.4
C1—C6—C5120.28 (14)O2—C17—C18111.98 (13)
C1—C6—S1112.45 (10)O2—C17—H17A109.2
C5—C6—S1127.27 (13)C18—C17—H17A109.2
N1—C7—C8124.16 (12)O2—C17—H17B109.2
N1—C7—C1123.24 (11)C18—C17—H17B109.2
C8—C7—C1112.60 (11)H17A—C17—H17B107.9
C7—C8—C9121.72 (12)C17—C18—H18A109.5
C7—C8—S1113.31 (10)C17—C18—H18B109.5
C9—C8—S1124.94 (10)H18A—C18—H18B109.5
O1—C9—N2121.14 (12)C17—C18—H18C109.5
O1—C9—C8127.18 (13)H18A—C18—H18C109.5
N2—C9—C8111.67 (11)H18B—C18—H18C109.5
N1—C10—O2121.38 (11)C10—N1—C7115.11 (11)
N1—C10—N2125.90 (11)C10—N2—C9121.35 (11)
O2—C10—N2112.70 (11)C10—N2—C11120.52 (10)
C12—C11—C16120.70 (13)C9—N2—C11118.13 (10)
C12—C11—N2120.16 (12)C10—O2—C17116.38 (10)
C16—C11—N2119.14 (13)C8—S1—C690.46 (7)
C6—C1—C2—C30.2 (2)C13—C14—C15—C160.1 (2)
C7—C1—C2—C3178.95 (14)C12—C11—C16—C150.5 (2)
C1—C2—C3—C41.0 (2)N2—C11—C16—C15179.39 (12)
C2—C3—C4—C50.8 (2)C14—C15—C16—C110.1 (2)
C3—C4—C5—C60.2 (2)O2—C10—N1—C7177.12 (12)
C2—C1—C6—C50.9 (2)N2—C10—N1—C71.9 (2)
C7—C1—C6—C5179.87 (12)C8—C7—N1—C100.30 (19)
C2—C1—C6—S1178.44 (11)C1—C7—N1—C10179.54 (12)
C7—C1—C6—S10.82 (15)N1—C10—N2—C91.4 (2)
C4—C5—C6—C11.0 (2)O2—C10—N2—C9177.65 (11)
C4—C5—C6—S1178.16 (12)N1—C10—N2—C11179.24 (13)
C2—C1—C7—N12.0 (2)O2—C10—N2—C111.71 (17)
C6—C1—C7—N1178.85 (12)O1—C9—N2—C10178.51 (14)
C2—C1—C7—C8177.88 (14)C8—C9—N2—C101.13 (18)
C6—C1—C7—C81.30 (17)O1—C9—N2—C112.1 (2)
N1—C7—C8—C92.9 (2)C8—C9—N2—C11178.24 (12)
C1—C7—C8—C9176.94 (12)C12—C11—N2—C1060.74 (17)
N1—C7—C8—S1178.93 (10)C16—C11—N2—C10119.17 (14)
C1—C7—C8—S11.22 (16)C12—C11—N2—C9119.88 (14)
C7—C8—C9—O1176.52 (15)C16—C11—N2—C960.21 (17)
S1—C8—C9—O11.4 (2)N1—C10—O2—C170.79 (18)
C7—C8—C9—N23.1 (2)N2—C10—O2—C17178.31 (11)
S1—C8—C9—N2178.98 (10)C18—C17—O2—C1078.89 (16)
C16—C11—C12—C130.9 (2)C7—C8—S1—C60.63 (12)
N2—C11—C12—C13178.97 (13)C9—C8—S1—C6177.45 (13)
C11—C12—C13—C140.9 (2)C1—C6—S1—C80.13 (11)
C12—C13—C14—C150.5 (3)C5—C6—S1—C8179.39 (14)
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds