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In the title compound, C14H10N2OS, the thienyl and phthalonitrile planes make a dihedral angle of 57.92 (2)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806034830/dn2060sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806034830/dn2060Isup2.hkl
Contains datablock I

CCDC reference: 624204

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.071
  • wR factor = 0.244
  • Data-to-parameter ratio = 15.6

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for S1 - C4 .. 10.50 su PLAT230_ALERT_2_B Hirshfeld Test Diff for C2 - C3 .. 16.03 su
Alert level C PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.70 mm PLAT230_ALERT_2_C Hirshfeld Test Diff for S1 - C1 .. 5.29 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for S1 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C2 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C3 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C4 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5 PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C11 - C13 ... 1.44 Ang. PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C12 - C14 ... 1.43 Ang.
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 9 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: WinGX (Farrugia, 1999) and PARST (Nardelli, 1995).

3-[2-(2-Thienyl)ethoxy]phthalonitrile top
Crystal data top
C14H10N2OSF(000) = 1056
Mr = 254.30Dx = 1.323 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 18471 reflections
a = 8.0888 (4) Åθ = 1.8–26.1°
b = 7.1356 (4) ŵ = 0.24 mm1
c = 44.235 (3) ÅT = 293 K
V = 2553.2 (3) Å3Plate, yellow
Z = 80.70 × 0.43 × 0.08 mm
Data collection top
Stoe IPDS-2
diffractometer
2537 independent reflections
Radiation source: fine-focus sealed tube1370 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.074
Detector resolution: 6.67 pixels mm-1θmax = 26.1°, θmin = 1.8°
ω scansh = 910
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
k = 88
Tmin = 0.865, Tmax = 0.982l = 5454
29377 measured reflections
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)] = 0.071Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.244H-atom parameters constrained
S = 0.95 w = 1/[σ2(Fo2) + (0.1655P)2]
where P = (Fo2 + 2Fc2)/3
2537 reflections(Δ/σ)max < 0.001
163 parametersΔρmax = 0.44 e Å3
0 restraintsΔρmin = 0.51 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
S10.86554 (19)0.1933 (3)0.67939 (3)0.1360 (7)
O10.9104 (2)0.0216 (3)0.61920 (5)0.0753 (7)
C120.7209 (3)0.0385 (4)0.58122 (7)0.0624 (8)
C70.8867 (4)0.0262 (4)0.59031 (7)0.0651 (8)
C100.8095 (4)0.1162 (5)0.53036 (8)0.0727 (8)
H100.78480.14570.51040.087*
C110.6848 (4)0.0827 (4)0.55102 (7)0.0655 (8)
C130.5156 (4)0.0934 (5)0.54137 (8)0.0736 (9)
C61.0815 (4)0.0380 (6)0.62962 (9)0.0807 (10)
H6A1.13700.08210.62810.097*
H6B1.14100.12820.61730.097*
C140.5895 (4)0.0052 (4)0.60214 (8)0.0687 (8)
C81.0098 (4)0.0604 (5)0.56937 (8)0.0713 (8)
H81.12020.05330.57510.086*
C90.9694 (4)0.1051 (5)0.53989 (8)0.0758 (9)
H91.05390.12830.52610.091*
N20.3812 (4)0.1018 (5)0.53336 (8)0.0961 (10)
N10.4787 (4)0.0210 (5)0.61748 (8)0.0933 (10)
C41.0272 (5)0.0460 (6)0.68439 (9)0.0860 (10)
C51.0764 (5)0.1020 (6)0.66211 (10)0.0915 (11)
H5A0.99930.20560.66370.110*
H5B1.18490.14870.66760.110*
C31.1163 (5)0.0794 (6)0.71388 (8)0.0898 (11)
H31.20920.01830.72140.108*
C10.8971 (8)0.2974 (9)0.71258 (11)0.1278 (18)
H10.83170.39500.71970.153*
C21.0225 (8)0.2289 (11)0.72761 (12)0.139 (2)
H21.05040.27530.74660.167*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.1341 (12)0.1580 (14)0.1158 (11)0.0312 (9)0.0051 (8)0.0051 (9)
O10.0534 (12)0.0932 (15)0.0792 (15)0.0004 (10)0.0025 (10)0.0035 (11)
C120.0541 (17)0.0583 (15)0.0748 (19)0.0029 (12)0.0034 (13)0.0062 (13)
C70.0597 (17)0.0642 (17)0.0712 (19)0.0018 (13)0.0029 (14)0.0043 (14)
C100.070 (2)0.0736 (19)0.074 (2)0.0002 (15)0.0031 (15)0.0028 (15)
C110.0590 (17)0.0605 (16)0.077 (2)0.0021 (13)0.0012 (14)0.0021 (14)
C130.068 (2)0.074 (2)0.079 (2)0.0005 (15)0.0048 (17)0.0011 (15)
C60.0552 (18)0.096 (2)0.090 (2)0.0063 (16)0.0078 (16)0.0007 (19)
C140.0574 (18)0.0702 (19)0.078 (2)0.0005 (13)0.0002 (16)0.0004 (15)
C80.0521 (16)0.0778 (19)0.084 (2)0.0021 (14)0.0027 (15)0.0085 (17)
C90.067 (2)0.077 (2)0.084 (2)0.0060 (15)0.0117 (17)0.0061 (16)
N20.069 (2)0.121 (3)0.098 (2)0.0021 (17)0.0109 (16)0.0088 (19)
N10.0711 (19)0.109 (2)0.100 (2)0.0034 (16)0.0110 (18)0.0000 (18)
C40.080 (2)0.097 (2)0.081 (2)0.0061 (19)0.0047 (18)0.0171 (19)
C50.077 (2)0.100 (3)0.098 (3)0.008 (2)0.0145 (19)0.010 (2)
C30.100 (3)0.098 (3)0.071 (2)0.004 (2)0.0048 (19)0.0023 (19)
C10.156 (5)0.131 (4)0.096 (3)0.007 (3)0.017 (3)0.011 (3)
C20.155 (5)0.178 (6)0.084 (3)0.019 (4)0.017 (3)0.001 (3)
Geometric parameters (Å, º) top
S1—C11.665 (5)C6—H6B0.9700
S1—C41.692 (4)C14—N11.139 (4)
O1—C71.336 (4)C8—C91.382 (5)
O1—C61.463 (4)C8—H80.9300
C12—C71.403 (4)C9—H90.9300
C12—C111.403 (4)C4—C51.498 (6)
C12—C141.430 (4)C4—C31.509 (5)
C7—C81.382 (4)C5—H5A0.9700
C10—C91.363 (5)C5—H5B0.9700
C10—C111.382 (4)C3—C21.444 (8)
C10—H100.9300C3—H30.9300
C11—C131.435 (5)C1—C21.308 (7)
C13—N21.145 (4)C1—H10.9300
C6—C51.509 (6)C2—H20.9300
C6—H6A0.9700
C1—S1—C492.5 (3)C7—C8—H8119.9
C7—O1—C6117.2 (3)C9—C8—H8119.9
C7—C12—C11119.1 (3)C10—C9—C8122.0 (3)
C7—C12—C14121.0 (3)C10—C9—H9119.0
C11—C12—C14119.9 (3)C8—C9—H9119.0
O1—C7—C8125.6 (3)C5—C4—C3123.6 (3)
O1—C7—C12115.3 (3)C5—C4—S1123.8 (3)
C8—C7—C12119.1 (3)C3—C4—S1112.6 (3)
C9—C10—C11118.6 (3)C4—C5—C6114.9 (3)
C9—C10—H10120.7C4—C5—H5A108.5
C11—C10—H10120.7C6—C5—H5A108.5
C10—C11—C12121.1 (3)C4—C5—H5B108.5
C10—C11—C13119.3 (3)C6—C5—H5B108.5
C12—C11—C13119.6 (3)H5A—C5—H5B107.5
N2—C13—C11179.3 (4)C2—C3—C4103.3 (4)
O1—C6—C5107.4 (3)C2—C3—H3128.4
O1—C6—H6A110.2C4—C3—H3128.4
C5—C6—H6A110.2C2—C1—S1113.6 (5)
O1—C6—H6B110.2C2—C1—H1123.2
C5—C6—H6B110.2S1—C1—H1123.2
H6A—C6—H6B108.5C1—C2—C3118.0 (5)
N1—C14—C12176.2 (4)C1—C2—H2121.0
C7—C8—C9120.2 (3)C3—C2—H2121.0
C6—O1—C7—C80.4 (5)C12—C7—C8—C90.3 (5)
C6—O1—C7—C12179.4 (3)C11—C10—C9—C80.4 (5)
C11—C12—C7—O1178.2 (3)C7—C8—C9—C100.3 (5)
C14—C12—C7—O11.2 (4)C1—S1—C4—C5178.9 (4)
C11—C12—C7—C80.9 (4)C1—S1—C4—C30.8 (3)
C14—C12—C7—C8179.7 (3)C3—C4—C5—C6134.5 (4)
C9—C10—C11—C120.1 (5)S1—C4—C5—C645.7 (5)
C9—C10—C11—C13179.9 (3)O1—C6—C5—C474.9 (4)
C7—C12—C11—C100.8 (4)C5—C4—C3—C2178.4 (4)
C14—C12—C11—C10179.8 (3)S1—C4—C3—C21.4 (4)
C7—C12—C11—C13179.2 (3)C4—S1—C1—C20.1 (5)
C14—C12—C11—C130.2 (4)S1—C1—C2—C31.0 (8)
C7—O1—C6—C5177.2 (3)C4—C3—C2—C11.5 (7)
O1—C7—C8—C9178.6 (3)
 

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