Download citation
Download citation
link to html
In the title compound, C22H16N2O2S2, two benzene rings are connected by a phthalo­nitrile moiety, the dihedral angle between them being 47.9 (2)°. The crystal structure is stabilized by intermolecular C—H...N contacts.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805008706/kp6030sup1.cif
Contains datablocks tuf2, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805008706/kp6030Isup2.hkl
Contains datablock I

CCDC reference: 270464

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.051
  • wR factor = 0.151
  • Data-to-parameter ratio = 19.7

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for N1 - C15 .. 12.48 su PLAT230_ALERT_2_B Hirshfeld Test Diff for N2 - C14 .. 12.52 su PLAT230_ALERT_2_B Hirshfeld Test Diff for O1 - C1 .. 13.43 su PLAT230_ALERT_2_B Hirshfeld Test Diff for O2 - C20 .. 10.60 su PLAT230_ALERT_2_B Hirshfeld Test Diff for O2 - C22 .. 13.63 su
Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 48 Perc. PLAT230_ALERT_2_C Hirshfeld Test Diff for O1 - C2 .. 6.23 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 S2 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for O1 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C14 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C15 PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C11 - C14 ... 1.43 Ang. PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C12 - C15 ... 1.42 Ang. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 4
0 ALERT level A = In general: serious problem 5 ALERT level B = Potentially serious problem 10 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 13 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 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: X-AREA (Stoe, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe, 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, 1997), PARST (Nardelli, 1995).

4,5-Bis(3-methoxythiophenoxy)phthalonitrile top
Crystal data top
C22H16N2O2S2Z = 2
Mr = 404.49F(000) = 420
Triclinic, P1Dx = 1.378 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.8208 (11) ÅCell parameters from 16920 reflections
b = 11.0356 (14) Åθ = 2.5–28.6°
c = 11.5767 (15) ŵ = 0.29 mm1
α = 91.531 (10)°T = 293 K
β = 102.391 (11)°Prism, yellow
γ = 91.567 (11)°0.30 × 0.22 × 0.12 mm
V = 975.0 (2) Å3
Data collection top
STOE IPDS 2
diffractometer
4979 independent reflections
Radiation source: fine-focus sealed tube2390 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.084
Detector resolution: 6.67 pixels mm-1θmax = 28.7°, θmin = 2.5°
ω scansh = 1010
Absorption correction: integration
X-RED32 (Stoe, 2002)
k = 1414
Tmin = 0.926, Tmax = 0.970l = 1415
25939 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)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.151H-atom parameters constrained
S = 0.85 w = 1/[σ2(Fo2) + (0.0861P)2]
where P = (Fo2 + 2Fc2)/3
4979 reflections(Δ/σ)max < 0.001
253 parametersΔρmax = 0.37 e Å3
0 restraintsΔρmin = 0.37 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 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
C10.8781 (5)0.0920 (4)0.2293 (4)0.0881 (12)
H1A0.95900.15530.22620.132*
H1B0.87270.07470.31010.132*
H1C0.91660.02030.19570.132*
C20.5790 (4)0.0509 (2)0.1593 (3)0.0482 (6)
C30.6012 (4)0.0672 (2)0.2041 (2)0.0474 (6)
H30.71180.09890.24010.057*
C40.4538 (4)0.1376 (2)0.1943 (2)0.0487 (6)
C50.2901 (4)0.0928 (3)0.1404 (3)0.0588 (8)
H50.19260.14010.13630.071*
C60.2726 (4)0.0239 (3)0.0924 (3)0.0576 (8)
H60.16290.05430.05310.069*
C70.4156 (4)0.0956 (2)0.1021 (3)0.0538 (7)
H70.40200.17430.07010.065*
C80.3794 (4)0.3834 (2)0.1655 (2)0.0457 (6)
C90.3315 (4)0.4937 (2)0.2137 (2)0.0460 (6)
C100.2514 (4)0.5801 (2)0.1379 (2)0.0464 (6)
H100.21950.65260.16900.056*
C110.2184 (3)0.5604 (2)0.0175 (2)0.0442 (6)
C120.2629 (3)0.4507 (2)0.0308 (2)0.0451 (6)
C130.3425 (4)0.3638 (2)0.0444 (2)0.0477 (6)
H130.37180.29080.01270.057*
C140.1372 (4)0.6521 (2)0.0581 (3)0.0503 (7)
C150.2284 (4)0.4308 (3)0.1552 (3)0.0544 (7)
C160.3268 (4)0.6616 (2)0.3976 (2)0.0492 (7)
C170.4301 (4)0.7570 (3)0.3745 (3)0.0578 (7)
H170.52420.74390.33890.069*
C180.3894 (5)0.8732 (3)0.4059 (3)0.0616 (8)
H180.45560.93920.38930.074*
C190.2539 (4)0.8922 (3)0.4607 (3)0.0592 (8)
H190.22890.97080.48140.071*
C200.1542 (4)0.7957 (3)0.4855 (3)0.0535 (7)
C210.1880 (4)0.6789 (3)0.4526 (2)0.0522 (7)
H210.11920.61340.46710.063*
C220.0838 (5)0.7287 (4)0.5684 (4)0.0919 (13)
H22A0.17030.76110.60730.138*
H22B0.01260.67410.61970.138*
H22C0.14120.68580.49670.138*
N10.1987 (5)0.4173 (3)0.2561 (3)0.1082 (10)
N20.0758 (4)0.7277 (3)0.1170 (3)0.0961 (9)
O10.7109 (3)0.12980 (18)0.1645 (2)0.0476 (6)
O20.0235 (3)0.8251 (2)0.5411 (2)0.0578 (7)
S10.48939 (12)0.28192 (7)0.26827 (7)0.0637 (3)
S20.37893 (13)0.50926 (7)0.36866 (7)0.0635 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.078 (3)0.077 (2)0.109 (3)0.026 (2)0.015 (2)0.005 (2)
C20.0569 (17)0.0422 (13)0.0470 (15)0.0100 (12)0.0132 (13)0.0033 (12)
C30.0550 (16)0.0417 (13)0.0454 (15)0.0050 (12)0.0102 (12)0.0009 (11)
C40.0608 (17)0.0390 (13)0.0478 (16)0.0090 (12)0.0141 (13)0.0032 (11)
C50.0536 (18)0.0533 (16)0.069 (2)0.0107 (14)0.0113 (15)0.0011 (15)
C60.0564 (18)0.0514 (16)0.063 (2)0.0037 (14)0.0086 (15)0.0007 (14)
C70.068 (2)0.0387 (14)0.0559 (18)0.0006 (13)0.0159 (15)0.0000 (12)
C80.0499 (15)0.0368 (12)0.0497 (16)0.0066 (11)0.0092 (12)0.0036 (11)
C90.0552 (16)0.0390 (13)0.0430 (15)0.0050 (12)0.0093 (12)0.0043 (11)
C100.0569 (16)0.0368 (12)0.0445 (15)0.0057 (12)0.0088 (12)0.0049 (11)
C110.0468 (15)0.0390 (13)0.0455 (15)0.0008 (11)0.0068 (12)0.0012 (11)
C120.0460 (15)0.0446 (14)0.0438 (15)0.0022 (11)0.0091 (12)0.0064 (11)
C130.0552 (16)0.0392 (13)0.0479 (16)0.0054 (12)0.0101 (13)0.0087 (12)
C140.0531 (16)0.0437 (14)0.0506 (17)0.0056 (12)0.0028 (13)0.0031 (13)
C150.0683 (19)0.0537 (16)0.0384 (16)0.0003 (14)0.0065 (14)0.0077 (13)
C160.0659 (18)0.0429 (14)0.0372 (14)0.0068 (13)0.0075 (13)0.0030 (11)
C170.0690 (19)0.0563 (17)0.0497 (17)0.0031 (15)0.0184 (15)0.0072 (14)
C180.083 (2)0.0496 (16)0.0550 (19)0.0083 (15)0.0221 (17)0.0076 (14)
C190.084 (2)0.0418 (15)0.0501 (17)0.0050 (14)0.0121 (16)0.0087 (13)
C200.0655 (19)0.0471 (15)0.0477 (16)0.0031 (14)0.0119 (14)0.0033 (12)
C210.0656 (18)0.0452 (14)0.0439 (16)0.0031 (13)0.0088 (13)0.0037 (12)
C220.082 (3)0.120 (3)0.080 (3)0.000 (2)0.034 (2)0.012 (2)
N10.135 (3)0.111 (2)0.075 (2)0.0021 (19)0.0148 (18)0.0096 (17)
N20.104 (2)0.0877 (19)0.092 (2)0.0189 (16)0.0070 (16)0.0108 (16)
O10.0472 (13)0.0360 (11)0.0572 (14)0.0136 (9)0.0056 (11)0.0067 (10)
O20.0590 (15)0.0517 (13)0.0718 (17)0.0035 (11)0.0352 (13)0.0096 (12)
S10.0893 (6)0.0429 (4)0.0517 (5)0.0213 (4)0.0026 (4)0.0060 (3)
S20.1019 (7)0.0450 (4)0.0415 (4)0.0198 (4)0.0095 (4)0.0033 (3)
Geometric parameters (Å, º) top
C1—O11.406 (4)C11—C121.404 (3)
C1—H1A0.9600C11—C141.427 (4)
C1—H1B0.9600C12—C131.381 (4)
C1—H1C0.9600C12—C151.417 (4)
C2—O11.361 (3)C13—H130.9300
C2—C71.378 (4)C14—N21.141 (4)
C2—C31.382 (4)C15—N11.146 (4)
C3—C41.394 (4)C16—C171.376 (4)
C3—H30.9300C16—C211.386 (4)
C4—C51.371 (4)C16—S21.780 (3)
C4—S11.775 (3)C17—C181.387 (4)
C5—C61.379 (4)C17—H170.9300
C5—H50.9300C18—C191.366 (4)
C6—C71.374 (4)C18—H180.9300
C6—H60.9300C19—C201.376 (4)
C7—H70.9300C19—H190.9300
C8—C131.380 (4)C20—O21.360 (4)
C8—C91.419 (3)C20—C211.383 (4)
C8—S11.759 (3)C21—H210.9300
C9—C101.382 (4)C22—O21.422 (5)
C9—S21.755 (3)C22—H22A0.9600
C10—C111.373 (4)C22—H22B0.9600
C10—H100.9300C22—H22C0.9600
O1—C1—H1A109.5C13—C12—C11119.1 (2)
O1—C1—H1B109.5C13—C12—C15120.9 (2)
H1A—C1—H1B109.5C11—C12—C15120.0 (3)
O1—C1—H1C109.5C8—C13—C12121.2 (2)
H1A—C1—H1C109.5C8—C13—H13119.4
H1B—C1—H1C109.5C12—C13—H13119.4
O1—C2—C7115.2 (2)N2—C14—C11178.1 (3)
O1—C2—C3124.4 (3)N1—C15—C12178.5 (3)
C7—C2—C3120.4 (2)C17—C16—C21121.9 (3)
C2—C3—C4118.4 (3)C17—C16—S2120.6 (2)
C2—C3—H3120.8C21—C16—S2117.3 (2)
C4—C3—H3120.8C16—C17—C18117.9 (3)
C5—C4—C3121.6 (3)C16—C17—H17121.0
C5—C4—S1122.5 (2)C18—C17—H17121.0
C3—C4—S1115.6 (2)C19—C18—C17121.1 (3)
C4—C5—C6118.8 (3)C19—C18—H18119.5
C4—C5—H5120.6C17—C18—H18119.5
C6—C5—H5120.6C18—C19—C20120.3 (3)
C7—C6—C5120.7 (3)C18—C19—H19119.9
C7—C6—H6119.6C20—C19—H19119.9
C5—C6—H6119.6O2—C20—C19115.3 (3)
C6—C7—C2120.1 (3)O2—C20—C21124.5 (3)
C6—C7—H7120.0C19—C20—C21120.2 (3)
C2—C7—H7120.0C20—C21—C16118.6 (3)
C13—C8—C9119.4 (2)C20—C21—H21120.7
C13—C8—S1124.68 (19)C16—C21—H21120.7
C9—C8—S1115.9 (2)O2—C22—H22A109.5
C10—C9—C8119.2 (2)O2—C22—H22B109.5
C10—C9—S2124.66 (19)H22A—C22—H22B109.5
C8—C9—S2116.2 (2)O2—C22—H22C109.5
C11—C10—C9120.9 (2)H22A—C22—H22C109.5
C11—C10—H10119.5H22B—C22—H22C109.5
C9—C10—H10119.5C2—O1—C1117.5 (2)
C10—C11—C12120.3 (2)C20—O2—C22117.6 (3)
C10—C11—C14119.4 (2)C8—S1—C4105.00 (13)
C12—C11—C14120.3 (3)C9—S2—C16104.28 (13)
O1—C2—C3—C4179.0 (3)C11—C12—C13—C80.3 (4)
C7—C2—C3—C42.5 (4)C15—C12—C13—C8178.8 (3)
C2—C3—C4—C50.8 (4)C21—C16—C17—C181.3 (5)
C2—C3—C4—S1173.3 (2)S2—C16—C17—C18175.9 (2)
C3—C4—C5—C61.7 (5)C16—C17—C18—C191.6 (5)
S1—C4—C5—C6175.3 (2)C17—C18—C19—C200.3 (5)
C4—C5—C6—C72.4 (5)C18—C19—C20—O2179.5 (3)
C5—C6—C7—C20.6 (5)C18—C19—C20—C211.5 (5)
O1—C2—C7—C6179.5 (3)O2—C20—C21—C16179.3 (3)
C3—C2—C7—C61.9 (4)C19—C20—C21—C161.8 (4)
C13—C8—C9—C101.0 (4)C17—C16—C21—C200.4 (4)
S1—C8—C9—C10177.2 (2)S2—C16—C21—C20174.4 (2)
C13—C8—C9—S2178.6 (2)C7—C2—O1—C1175.5 (3)
S1—C8—C9—S23.2 (3)C3—C2—O1—C16.0 (5)
C8—C9—C10—C110.1 (4)C19—C20—O2—C22179.8 (3)
S2—C9—C10—C11179.7 (2)C21—C20—O2—C220.9 (5)
C9—C10—C11—C121.1 (4)C13—C8—S1—C424.4 (3)
C9—C10—C11—C14179.3 (3)C9—C8—S1—C4157.4 (2)
C10—C11—C12—C130.9 (4)C5—C4—S1—C851.8 (3)
C14—C11—C12—C13179.5 (3)C3—C4—S1—C8134.2 (2)
C10—C11—C12—C15180.0 (3)C10—C9—S2—C167.0 (3)
C14—C11—C12—C150.4 (4)C8—C9—S2—C16173.4 (2)
C9—C8—C13—C121.2 (4)C17—C16—S2—C971.0 (3)
S1—C8—C13—C12176.9 (2)C21—C16—S2—C9114.1 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H5···N2i0.932.563.493 (4)178
Symmetry code: (i) x, y+1, z.
 

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