In the title compound, C
22H
16N
2O
2S
2, 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
CCDC reference: 270464
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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
C22H16N2O2S2 | Z = 2 |
Mr = 404.49 | F(000) = 420 |
Triclinic, P1 | Dx = 1.378 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.8208 (11) Å | Cell parameters from 16920 reflections |
b = 11.0356 (14) Å | θ = 2.5–28.6° |
c = 11.5767 (15) Å | µ = 0.29 mm−1 |
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 tube | 2390 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.084 |
Detector resolution: 6.67 pixels mm-1 | θmax = 28.7°, θmin = 2.5° |
ω scans | h = −10→10 |
Absorption correction: integration X-RED32 (Stoe, 2002) | k = −14→14 |
Tmin = 0.926, Tmax = 0.970 | l = −14→15 |
25939 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.051 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.151 | H-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 parameters | Δρmax = 0.37 e Å−3 |
0 restraints | Δρmin = −0.37 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
C1 | 0.8781 (5) | −0.0920 (4) | 0.2293 (4) | 0.0881 (12) | |
H1A | 0.9590 | −0.1553 | 0.2262 | 0.132* | |
H1B | 0.8727 | −0.0747 | 0.3101 | 0.132* | |
H1C | 0.9166 | −0.0203 | 0.1957 | 0.132* | |
C2 | 0.5790 (4) | −0.0509 (2) | 0.1593 (3) | 0.0482 (6) | |
C3 | 0.6012 (4) | 0.0672 (2) | 0.2041 (2) | 0.0474 (6) | |
H3 | 0.7118 | 0.0989 | 0.2401 | 0.057* | |
C4 | 0.4538 (4) | 0.1376 (2) | 0.1943 (2) | 0.0487 (6) | |
C5 | 0.2901 (4) | 0.0928 (3) | 0.1404 (3) | 0.0588 (8) | |
H5 | 0.1926 | 0.1401 | 0.1363 | 0.071* | |
C6 | 0.2726 (4) | −0.0239 (3) | 0.0924 (3) | 0.0576 (8) | |
H6 | 0.1629 | −0.0543 | 0.0531 | 0.069* | |
C7 | 0.4156 (4) | −0.0956 (2) | 0.1021 (3) | 0.0538 (7) | |
H7 | 0.4020 | −0.1743 | 0.0701 | 0.065* | |
C8 | 0.3794 (4) | 0.3834 (2) | 0.1655 (2) | 0.0457 (6) | |
C9 | 0.3315 (4) | 0.4937 (2) | 0.2137 (2) | 0.0460 (6) | |
C10 | 0.2514 (4) | 0.5801 (2) | 0.1379 (2) | 0.0464 (6) | |
H10 | 0.2195 | 0.6526 | 0.1690 | 0.056* | |
C11 | 0.2184 (3) | 0.5604 (2) | 0.0175 (2) | 0.0442 (6) | |
C12 | 0.2629 (3) | 0.4507 (2) | −0.0308 (2) | 0.0451 (6) | |
C13 | 0.3425 (4) | 0.3638 (2) | 0.0444 (2) | 0.0477 (6) | |
H13 | 0.3718 | 0.2908 | 0.0127 | 0.057* | |
C14 | 0.1372 (4) | 0.6521 (2) | −0.0581 (3) | 0.0503 (7) | |
C15 | 0.2284 (4) | 0.4308 (3) | −0.1552 (3) | 0.0544 (7) | |
C16 | 0.3268 (4) | 0.6616 (2) | 0.3976 (2) | 0.0492 (7) | |
C17 | 0.4301 (4) | 0.7570 (3) | 0.3745 (3) | 0.0578 (7) | |
H17 | 0.5242 | 0.7439 | 0.3389 | 0.069* | |
C18 | 0.3894 (5) | 0.8732 (3) | 0.4059 (3) | 0.0616 (8) | |
H18 | 0.4556 | 0.9392 | 0.3893 | 0.074* | |
C19 | 0.2539 (4) | 0.8922 (3) | 0.4607 (3) | 0.0592 (8) | |
H19 | 0.2289 | 0.9708 | 0.4814 | 0.071* | |
C20 | 0.1542 (4) | 0.7957 (3) | 0.4855 (3) | 0.0535 (7) | |
C21 | 0.1880 (4) | 0.6789 (3) | 0.4526 (2) | 0.0522 (7) | |
H21 | 0.1192 | 0.6134 | 0.4671 | 0.063* | |
C22 | −0.0838 (5) | 0.7287 (4) | 0.5684 (4) | 0.0919 (13) | |
H22A | −0.1703 | 0.7611 | 0.6073 | 0.138* | |
H22B | −0.0126 | 0.6741 | 0.6197 | 0.138* | |
H22C | −0.1412 | 0.6858 | 0.4967 | 0.138* | |
N1 | 0.1987 (5) | 0.4173 (3) | −0.2561 (3) | 0.1082 (10) | |
N2 | 0.0758 (4) | 0.7277 (3) | −0.1170 (3) | 0.0961 (9) | |
O1 | 0.7109 (3) | −0.12980 (18) | 0.1645 (2) | 0.0476 (6) | |
O2 | 0.0235 (3) | 0.8251 (2) | 0.5411 (2) | 0.0578 (7) | |
S1 | 0.48939 (12) | 0.28192 (7) | 0.26827 (7) | 0.0637 (3) | |
S2 | 0.37893 (13) | 0.50926 (7) | 0.36866 (7) | 0.0635 (3) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.078 (3) | 0.077 (2) | 0.109 (3) | 0.026 (2) | 0.015 (2) | −0.005 (2) |
C2 | 0.0569 (17) | 0.0422 (13) | 0.0470 (15) | 0.0100 (12) | 0.0132 (13) | 0.0033 (12) |
C3 | 0.0550 (16) | 0.0417 (13) | 0.0454 (15) | 0.0050 (12) | 0.0102 (12) | −0.0009 (11) |
C4 | 0.0608 (17) | 0.0390 (13) | 0.0478 (16) | 0.0090 (12) | 0.0141 (13) | 0.0032 (11) |
C5 | 0.0536 (18) | 0.0533 (16) | 0.069 (2) | 0.0107 (14) | 0.0113 (15) | 0.0011 (15) |
C6 | 0.0564 (18) | 0.0514 (16) | 0.063 (2) | −0.0037 (14) | 0.0086 (15) | −0.0007 (14) |
C7 | 0.068 (2) | 0.0387 (14) | 0.0559 (18) | −0.0006 (13) | 0.0159 (15) | 0.0000 (12) |
C8 | 0.0499 (15) | 0.0368 (12) | 0.0497 (16) | 0.0066 (11) | 0.0092 (12) | −0.0036 (11) |
C9 | 0.0552 (16) | 0.0390 (13) | 0.0430 (15) | 0.0050 (12) | 0.0093 (12) | −0.0043 (11) |
C10 | 0.0569 (16) | 0.0368 (12) | 0.0445 (15) | 0.0057 (12) | 0.0088 (12) | −0.0049 (11) |
C11 | 0.0468 (15) | 0.0390 (13) | 0.0455 (15) | 0.0008 (11) | 0.0068 (12) | 0.0012 (11) |
C12 | 0.0460 (15) | 0.0446 (14) | 0.0438 (15) | −0.0022 (11) | 0.0091 (12) | −0.0064 (11) |
C13 | 0.0552 (16) | 0.0392 (13) | 0.0479 (16) | 0.0054 (12) | 0.0101 (13) | −0.0087 (12) |
C14 | 0.0531 (16) | 0.0437 (14) | 0.0506 (17) | 0.0056 (12) | 0.0028 (13) | 0.0031 (13) |
C15 | 0.0683 (19) | 0.0537 (16) | 0.0384 (16) | 0.0003 (14) | 0.0065 (14) | −0.0077 (13) |
C16 | 0.0659 (18) | 0.0429 (14) | 0.0372 (14) | 0.0068 (13) | 0.0075 (13) | −0.0030 (11) |
C17 | 0.0690 (19) | 0.0563 (17) | 0.0497 (17) | −0.0031 (15) | 0.0184 (15) | −0.0072 (14) |
C18 | 0.083 (2) | 0.0496 (16) | 0.0550 (19) | −0.0083 (15) | 0.0221 (17) | −0.0076 (14) |
C19 | 0.084 (2) | 0.0418 (15) | 0.0501 (17) | 0.0050 (14) | 0.0121 (16) | −0.0087 (13) |
C20 | 0.0655 (19) | 0.0471 (15) | 0.0477 (16) | 0.0031 (14) | 0.0119 (14) | −0.0033 (12) |
C21 | 0.0656 (18) | 0.0452 (14) | 0.0439 (16) | −0.0031 (13) | 0.0088 (13) | −0.0037 (12) |
C22 | 0.082 (3) | 0.120 (3) | 0.080 (3) | 0.000 (2) | 0.034 (2) | −0.012 (2) |
N1 | 0.135 (3) | 0.111 (2) | 0.075 (2) | 0.0021 (19) | 0.0148 (18) | −0.0096 (17) |
N2 | 0.104 (2) | 0.0877 (19) | 0.092 (2) | 0.0189 (16) | 0.0070 (16) | 0.0108 (16) |
O1 | 0.0472 (13) | 0.0360 (11) | 0.0572 (14) | 0.0136 (9) | 0.0056 (11) | −0.0067 (10) |
O2 | 0.0590 (15) | 0.0517 (13) | 0.0718 (17) | 0.0035 (11) | 0.0352 (13) | −0.0096 (12) |
S1 | 0.0893 (6) | 0.0429 (4) | 0.0517 (5) | 0.0213 (4) | −0.0026 (4) | −0.0060 (3) |
S2 | 0.1019 (7) | 0.0450 (4) | 0.0415 (4) | 0.0198 (4) | 0.0095 (4) | −0.0033 (3) |
Geometric parameters (Å, º) top
C1—O1 | 1.406 (4) | C11—C12 | 1.404 (3) |
C1—H1A | 0.9600 | C11—C14 | 1.427 (4) |
C1—H1B | 0.9600 | C12—C13 | 1.381 (4) |
C1—H1C | 0.9600 | C12—C15 | 1.417 (4) |
C2—O1 | 1.361 (3) | C13—H13 | 0.9300 |
C2—C7 | 1.378 (4) | C14—N2 | 1.141 (4) |
C2—C3 | 1.382 (4) | C15—N1 | 1.146 (4) |
C3—C4 | 1.394 (4) | C16—C17 | 1.376 (4) |
C3—H3 | 0.9300 | C16—C21 | 1.386 (4) |
C4—C5 | 1.371 (4) | C16—S2 | 1.780 (3) |
C4—S1 | 1.775 (3) | C17—C18 | 1.387 (4) |
C5—C6 | 1.379 (4) | C17—H17 | 0.9300 |
C5—H5 | 0.9300 | C18—C19 | 1.366 (4) |
C6—C7 | 1.374 (4) | C18—H18 | 0.9300 |
C6—H6 | 0.9300 | C19—C20 | 1.376 (4) |
C7—H7 | 0.9300 | C19—H19 | 0.9300 |
C8—C13 | 1.380 (4) | C20—O2 | 1.360 (4) |
C8—C9 | 1.419 (3) | C20—C21 | 1.383 (4) |
C8—S1 | 1.759 (3) | C21—H21 | 0.9300 |
C9—C10 | 1.382 (4) | C22—O2 | 1.422 (5) |
C9—S2 | 1.755 (3) | C22—H22A | 0.9600 |
C10—C11 | 1.373 (4) | C22—H22B | 0.9600 |
C10—H10 | 0.9300 | C22—H22C | 0.9600 |
| | | |
O1—C1—H1A | 109.5 | C13—C12—C11 | 119.1 (2) |
O1—C1—H1B | 109.5 | C13—C12—C15 | 120.9 (2) |
H1A—C1—H1B | 109.5 | C11—C12—C15 | 120.0 (3) |
O1—C1—H1C | 109.5 | C8—C13—C12 | 121.2 (2) |
H1A—C1—H1C | 109.5 | C8—C13—H13 | 119.4 |
H1B—C1—H1C | 109.5 | C12—C13—H13 | 119.4 |
O1—C2—C7 | 115.2 (2) | N2—C14—C11 | 178.1 (3) |
O1—C2—C3 | 124.4 (3) | N1—C15—C12 | 178.5 (3) |
C7—C2—C3 | 120.4 (2) | C17—C16—C21 | 121.9 (3) |
C2—C3—C4 | 118.4 (3) | C17—C16—S2 | 120.6 (2) |
C2—C3—H3 | 120.8 | C21—C16—S2 | 117.3 (2) |
C4—C3—H3 | 120.8 | C16—C17—C18 | 117.9 (3) |
C5—C4—C3 | 121.6 (3) | C16—C17—H17 | 121.0 |
C5—C4—S1 | 122.5 (2) | C18—C17—H17 | 121.0 |
C3—C4—S1 | 115.6 (2) | C19—C18—C17 | 121.1 (3) |
C4—C5—C6 | 118.8 (3) | C19—C18—H18 | 119.5 |
C4—C5—H5 | 120.6 | C17—C18—H18 | 119.5 |
C6—C5—H5 | 120.6 | C18—C19—C20 | 120.3 (3) |
C7—C6—C5 | 120.7 (3) | C18—C19—H19 | 119.9 |
C7—C6—H6 | 119.6 | C20—C19—H19 | 119.9 |
C5—C6—H6 | 119.6 | O2—C20—C19 | 115.3 (3) |
C6—C7—C2 | 120.1 (3) | O2—C20—C21 | 124.5 (3) |
C6—C7—H7 | 120.0 | C19—C20—C21 | 120.2 (3) |
C2—C7—H7 | 120.0 | C20—C21—C16 | 118.6 (3) |
C13—C8—C9 | 119.4 (2) | C20—C21—H21 | 120.7 |
C13—C8—S1 | 124.68 (19) | C16—C21—H21 | 120.7 |
C9—C8—S1 | 115.9 (2) | O2—C22—H22A | 109.5 |
C10—C9—C8 | 119.2 (2) | O2—C22—H22B | 109.5 |
C10—C9—S2 | 124.66 (19) | H22A—C22—H22B | 109.5 |
C8—C9—S2 | 116.2 (2) | O2—C22—H22C | 109.5 |
C11—C10—C9 | 120.9 (2) | H22A—C22—H22C | 109.5 |
C11—C10—H10 | 119.5 | H22B—C22—H22C | 109.5 |
C9—C10—H10 | 119.5 | C2—O1—C1 | 117.5 (2) |
C10—C11—C12 | 120.3 (2) | C20—O2—C22 | 117.6 (3) |
C10—C11—C14 | 119.4 (2) | C8—S1—C4 | 105.00 (13) |
C12—C11—C14 | 120.3 (3) | C9—S2—C16 | 104.28 (13) |
| | | |
O1—C2—C3—C4 | −179.0 (3) | C11—C12—C13—C8 | −0.3 (4) |
C7—C2—C3—C4 | 2.5 (4) | C15—C12—C13—C8 | 178.8 (3) |
C2—C3—C4—C5 | −0.8 (4) | C21—C16—C17—C18 | −1.3 (5) |
C2—C3—C4—S1 | 173.3 (2) | S2—C16—C17—C18 | −175.9 (2) |
C3—C4—C5—C6 | −1.7 (5) | C16—C17—C18—C19 | 1.6 (5) |
S1—C4—C5—C6 | −175.3 (2) | C17—C18—C19—C20 | −0.3 (5) |
C4—C5—C6—C7 | 2.4 (5) | C18—C19—C20—O2 | 179.5 (3) |
C5—C6—C7—C2 | −0.6 (5) | C18—C19—C20—C21 | −1.5 (5) |
O1—C2—C7—C6 | 179.5 (3) | O2—C20—C21—C16 | −179.3 (3) |
C3—C2—C7—C6 | −1.9 (4) | C19—C20—C21—C16 | 1.8 (4) |
C13—C8—C9—C10 | −1.0 (4) | C17—C16—C21—C20 | −0.4 (4) |
S1—C8—C9—C10 | 177.2 (2) | S2—C16—C21—C20 | 174.4 (2) |
C13—C8—C9—S2 | 178.6 (2) | C7—C2—O1—C1 | −175.5 (3) |
S1—C8—C9—S2 | −3.2 (3) | C3—C2—O1—C1 | 6.0 (5) |
C8—C9—C10—C11 | −0.1 (4) | C19—C20—O2—C22 | 179.8 (3) |
S2—C9—C10—C11 | −179.7 (2) | C21—C20—O2—C22 | 0.9 (5) |
C9—C10—C11—C12 | 1.1 (4) | C13—C8—S1—C4 | −24.4 (3) |
C9—C10—C11—C14 | −179.3 (3) | C9—C8—S1—C4 | 157.4 (2) |
C10—C11—C12—C13 | −0.9 (4) | C5—C4—S1—C8 | −51.8 (3) |
C14—C11—C12—C13 | 179.5 (3) | C3—C4—S1—C8 | 134.2 (2) |
C10—C11—C12—C15 | 180.0 (3) | C10—C9—S2—C16 | −7.0 (3) |
C14—C11—C12—C15 | 0.4 (4) | C8—C9—S2—C16 | 173.4 (2) |
C9—C8—C13—C12 | 1.2 (4) | C17—C16—S2—C9 | −71.0 (3) |
S1—C8—C13—C12 | −176.9 (2) | C21—C16—S2—C9 | 114.1 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···N2i | 0.93 | 2.56 | 3.493 (4) | 178 |
Symmetry code: (i) −x, −y+1, −z. |