2,7-Bis(3,4-di­cyano­phenoxy)­naphthalene

The mol­ecule of the title compound, 4,4′-naphthalene-2,7-dioxy­di­benzene-1,2-dicarbo­nitrile, C₂₆H₁₂N₄O₂, has an asymmetric conformation, with the two benzene rings approx­imately orthogonal to each other [dihedral angle = 77.18 (5)°] and forming unequal dihedral angles of 55.14 (5) and 67.62 (5)° with the naphthalene plane. The structure is stabilized by relatively weak C—H...N interactions, linking the mol­ecules into infinite chains running along the diagonal of the ac plane of the unit cell.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.036
• wR factor = 0.084
• Data-to-parameter ratio = 13.3

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSMU01_ALERT_1_C  The ratio of given/expected absorption coefficient lies
               outside the range 0.99 <> 1.01
            Calculated value of mu =     0.092
            Value of mu given      =     0.090
GOODF01_ALERT_2_C  The least squares goodness of fit parameter lies
            outside the range 0.80 <> 2.00
            Goodness of fit given =      0.770
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C1     -   C8       =       5.81 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C21    -   C22      =       5.84 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C22    -   C26      =       6.14 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C23    -   C25      =       6.78 su
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C1     -   C8       =       1.43 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C2     -   C3       =       1.43 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C22    -   C26      =       1.44 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C23    -   C25      =       1.44 Ang.
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         49
            C4  -C3  -C2  -N2   -159.00100.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         50
            C8  -C3  -C2  -N2     20.00 51.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         54
            C24 -C23 -C25 -N3     78.00  6.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         55
            C22 -C23 -C25 -N3   -100.00  6.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         56
            C21 -C22 -C26 -N4    -69.00 13.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         57
            C23 -C22 -C26 -N4    109.00 13.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         63
            C7  -C8  -C1  -N1   -160.00 11.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         64
            C3  -C8  -C1  -N1     18.00 11.00   1.555   1.555   1.555   1.555

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  18 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
   9 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
   8 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED (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, 1997) and PARST (Nardelli, 1995).

4,4'-Naphthalene-2,7-dioxydibenzene-1,2-dicarbonitrile

Crystal data

C26H12N4O2	F(000) = 848
Mr = 412.40	Dx = 1.399 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 8818 reflections
a = 8.3592 (10) Å	θ = 2.0–25.7°
b = 7.5300 (5) Å	µ = 0.09 mm^−1
c = 31.368 (3) Å	T = 293 K
β = 97.400 (9)°	Prismatic, colourless
V = 1958.0 (3) Å^3	0.50 × 0.31 × 0.07 mm
Z = 4

Data collection

Stoe IPDS-2 diffractometer	1929 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.064
Graphite monochromator	θmax = 26.0°, θmin = 2.5°
Detector resolution: 6.67 pixels mm^-1	h = −10→10
ω scans	k = −9→9
21357 measured reflections	l = −38→38
3856 independent reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.036	H-atom parameters constrained
wR(F^2) = 0.084	w = 1/[σ^2(Fo^2) + (0.0424P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.77	(Δ/σ)max = 0.001
3856 reflections	Δρmax = 0.13 e Å^−3
290 parameters	Δρmin = −0.13 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0097 (8)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.73249 (15)	0.29816 (18)	0.25158 (4)	0.0642 (4)
O2	0.06903 (14)	0.03890 (17)	0.09202 (4)	0.0591 (4)
C16	0.2977 (2)	0.1342 (2)	0.14229 (5)	0.0503 (5)
H16	0.3694	0.0752	0.1269	0.060*
C18	0.5192 (2)	0.2184 (2)	0.19854 (5)	0.0506 (5)
H18	0.5940	0.1586	0.1843	0.061*
C12	0.2434 (2)	0.3141 (2)	0.20340 (5)	0.0478 (4)
C17	0.3553 (2)	0.2231 (2)	0.18103 (5)	0.0455 (4)
C15	0.1377 (2)	0.1353 (2)	0.12778 (5)	0.0497 (5)
C14	0.0251 (2)	0.2222 (2)	0.14978 (6)	0.0551 (5)
H14	−0.0842	0.2197	0.1394	0.066*
C9	0.5670 (2)	0.3017 (2)	0.23636 (6)	0.0530 (5)
C4	0.9506 (2)	0.2419 (2)	0.30314 (6)	0.0538 (5)
H4	1.0160	0.2817	0.2833	0.065*
C13	0.0783 (2)	0.3101 (2)	0.18655 (6)	0.0543 (5)
H13	0.0042	0.3694	0.2011	0.065*
C10	0.4601 (3)	0.4000 (2)	0.25771 (6)	0.0596 (5)
H10	0.4971	0.4617	0.2827	0.071*
C5	0.7850 (2)	0.2410 (2)	0.29267 (5)	0.0524 (5)
C11	0.3015 (2)	0.4045 (2)	0.24159 (6)	0.0565 (5)
H11	0.2299	0.4684	0.2560	0.068*
C24	0.1268 (2)	−0.1447 (3)	0.03630 (5)	0.0506 (5)
H24	0.0722	−0.2361	0.0482	0.061*
C3	1.0190 (2)	0.1839 (2)	0.34300 (6)	0.0508 (5)
C8	0.9208 (2)	0.1263 (2)	0.37297 (5)	0.0522 (5)
C19	0.1498 (2)	0.0169 (3)	0.05695 (5)	0.0488 (5)
C23	0.1868 (2)	−0.1680 (3)	−0.00255 (5)	0.0498 (5)
C22	0.2702 (2)	−0.0312 (3)	−0.01989 (5)	0.0511 (5)
C7	0.7554 (2)	0.1273 (3)	0.36213 (6)	0.0586 (5)
H7	0.6894	0.0900	0.3821	0.070*
C2	1.1910 (3)	0.1813 (3)	0.35332 (6)	0.0603 (5)
C6	0.6871 (2)	0.1831 (2)	0.32191 (6)	0.0568 (5)
H6	0.5757	0.1815	0.3146	0.068*
C25	0.1560 (2)	−0.3325 (3)	−0.02555 (6)	0.0609 (5)
C26	0.3246 (2)	−0.0518 (3)	−0.06134 (7)	0.0646 (6)
C21	0.2951 (2)	0.1267 (3)	0.00232 (6)	0.0580 (5)
H21	0.3534	0.2172	−0.0087	0.070*
C20	0.2345 (2)	0.1516 (3)	0.04061 (6)	0.0558 (5)
H20	0.2508	0.2586	0.0553	0.067*
N3	0.1270 (2)	−0.4615 (3)	−0.04421 (6)	0.0845 (6)
N1	1.0527 (2)	0.0304 (3)	0.44813 (6)	0.0895 (6)
N2	1.3276 (2)	0.1787 (3)	0.36167 (6)	0.0832 (6)
C1	0.9928 (2)	0.0721 (3)	0.41484 (7)	0.0641 (6)
N4	0.3655 (2)	−0.0660 (3)	−0.09433 (6)	0.0894 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0586 (9)	0.0870 (10)	0.0463 (7)	−0.0125 (7)	0.0040 (6)	0.0055 (7)
O2	0.0520 (7)	0.0769 (9)	0.0485 (7)	−0.0082 (7)	0.0074 (6)	−0.0108 (7)
C16	0.0499 (11)	0.0575 (12)	0.0445 (10)	0.0064 (9)	0.0099 (9)	−0.0016 (9)
C18	0.0530 (12)	0.0548 (12)	0.0446 (10)	0.0003 (9)	0.0087 (9)	−0.0004 (9)
C12	0.0604 (12)	0.0411 (10)	0.0431 (10)	0.0060 (9)	0.0114 (9)	0.0034 (8)
C17	0.0530 (11)	0.0438 (11)	0.0405 (10)	0.0014 (9)	0.0095 (8)	0.0021 (8)
C15	0.0520 (12)	0.0533 (12)	0.0440 (10)	0.0005 (9)	0.0063 (9)	−0.0010 (9)
C14	0.0506 (11)	0.0628 (13)	0.0522 (11)	0.0087 (10)	0.0082 (9)	0.0027 (10)
C9	0.0558 (12)	0.0560 (13)	0.0464 (11)	−0.0064 (10)	0.0043 (9)	0.0019 (9)
C4	0.0523 (12)	0.0588 (12)	0.0518 (11)	−0.0102 (9)	0.0130 (9)	−0.0066 (9)
C13	0.0575 (12)	0.0551 (12)	0.0523 (11)	0.0122 (10)	0.0147 (9)	0.0037 (9)
C10	0.0755 (15)	0.0533 (13)	0.0498 (11)	−0.0052 (11)	0.0077 (10)	−0.0063 (9)
C5	0.0553 (12)	0.0579 (12)	0.0429 (10)	−0.0097 (9)	0.0027 (9)	−0.0023 (9)
C11	0.0726 (14)	0.0496 (12)	0.0499 (11)	0.0054 (10)	0.0180 (10)	−0.0021 (9)
C24	0.0480 (11)	0.0544 (12)	0.0482 (10)	−0.0003 (9)	0.0016 (8)	0.0027 (9)
C3	0.0472 (11)	0.0530 (12)	0.0523 (11)	−0.0020 (9)	0.0063 (9)	−0.0103 (9)
C8	0.0542 (12)	0.0554 (12)	0.0464 (10)	−0.0004 (9)	0.0039 (9)	−0.0025 (9)
C19	0.0409 (10)	0.0642 (13)	0.0406 (10)	0.0045 (9)	0.0029 (8)	0.0008 (9)
C23	0.0438 (10)	0.0575 (12)	0.0471 (10)	0.0053 (9)	0.0019 (8)	−0.0027 (9)
C22	0.0401 (10)	0.0672 (13)	0.0457 (10)	0.0027 (9)	0.0042 (8)	0.0009 (10)
C7	0.0546 (13)	0.0699 (14)	0.0516 (11)	−0.0068 (10)	0.0084 (9)	0.0057 (10)
C2	0.0532 (13)	0.0667 (14)	0.0612 (12)	−0.0024 (11)	0.0081 (10)	−0.0145 (10)
C6	0.0476 (11)	0.0662 (13)	0.0563 (12)	−0.0097 (10)	0.0055 (9)	0.0032 (10)
C25	0.0609 (13)	0.0688 (14)	0.0532 (12)	0.0057 (11)	0.0081 (10)	−0.0018 (11)
C26	0.0437 (11)	0.0908 (16)	0.0598 (13)	0.0009 (11)	0.0085 (10)	0.0014 (11)
C21	0.0482 (11)	0.0707 (15)	0.0546 (12)	−0.0068 (10)	0.0050 (9)	0.0086 (10)
C20	0.0530 (11)	0.0610 (13)	0.0519 (11)	−0.0067 (10)	0.0005 (9)	−0.0002 (10)
N3	0.0979 (15)	0.0804 (14)	0.0760 (13)	−0.0004 (12)	0.0146 (11)	−0.0187 (11)
N1	0.0832 (14)	0.1134 (16)	0.0692 (12)	0.0141 (12)	−0.0007 (10)	0.0146 (12)
N2	0.0593 (12)	0.0959 (15)	0.0934 (14)	−0.0015 (10)	0.0058 (10)	−0.0274 (11)
C1	0.0568 (13)	0.0740 (15)	0.0610 (13)	0.0045 (11)	0.0050 (10)	0.0017 (11)
N4	0.0719 (12)	0.1353 (18)	0.0649 (12)	0.0032 (12)	0.0242 (10)	−0.0034 (11)

Geometric parameters (Å, º)

O1—C5	1.376 (2)	C13—H13	0.9300
O1—C9	1.405 (2)	C10—C11	1.357 (3)
O2—C15	1.3961 (19)	C10—H10	0.9300
O2—C19	1.3730 (19)	C5—C6	1.376 (2)
N1—C1	1.142 (2)	C11—H11	0.9300
N2—C2	1.139 (2)	C24—C19	1.380 (2)
N3—C25	1.144 (2)	C24—C23	1.387 (2)
N4—C26	1.136 (2)	C24—H24	0.9300
C16—C15	1.356 (2)	C3—C8	1.395 (2)
C16—C17	1.416 (2)	C3—C2	1.432 (3)
C16—H16	0.9300	C8—C7	1.381 (2)
C18—C9	1.356 (2)	C8—C1	1.432 (3)
C18—C17	1.410 (2)	C19—C20	1.373 (2)
C18—H18	0.9300	C23—C22	1.393 (2)
C12—C11	1.409 (2)	C23—C25	1.440 (3)
C12—C13	1.413 (2)	C22—C21	1.380 (2)
C12—C17	1.416 (2)	C22—C26	1.440 (3)
C15—C14	1.399 (2)	C7—C6	1.382 (2)
C14—C13	1.354 (2)	C7—H7	0.9300
C14—H14	0.9300	C6—H6	0.9300
C9—C10	1.396 (2)	C21—C20	1.375 (2)
C4—C3	1.377 (2)	C21—H21	0.9300
C4—C5	1.381 (2)	C20—H20	0.9300
C4—H4	0.9300
C5—O1—C9	120.36 (14)	C10—C11—H11	119.4
C19—O2—C15	120.85 (13)	C12—C11—H11	119.4
C15—C16—C17	119.75 (17)	C19—C24—C23	118.65 (17)
C15—C16—H16	120.1	C19—C24—H24	120.7
C17—C16—H16	120.1	C23—C24—H24	120.7
C9—C18—C17	119.41 (17)	C4—C3—C8	119.95 (16)
C9—C18—H18	120.3	C4—C3—C2	119.78 (17)
C17—C18—H18	120.3	C8—C3—C2	120.28 (17)
C11—C12—C13	122.82 (17)	C7—C8—C3	119.34 (16)
C11—C12—C17	118.53 (17)	C7—C8—C1	121.09 (17)
C13—C12—C17	118.65 (16)	C3—C8—C1	119.55 (17)
C18—C17—C12	119.35 (16)	O2—C19—C20	122.69 (17)
C18—C17—C16	121.87 (16)	O2—C19—C24	115.43 (16)
C12—C17—C16	118.75 (16)	C20—C19—C24	121.55 (16)
C16—C15—O2	123.51 (16)	C24—C23—C22	120.35 (17)
C16—C15—C14	122.30 (17)	C24—C23—C25	119.15 (17)
O2—C15—C14	113.99 (16)	C22—C23—C25	120.46 (16)
C13—C14—C15	118.72 (18)	C21—C22—C23	119.36 (16)
C13—C14—H14	120.6	C21—C22—C26	120.25 (18)
C15—C14—H14	120.6	C23—C22—C26	120.34 (18)
C18—C9—C10	122.03 (18)	C8—C7—C6	120.63 (17)
C18—C9—O1	117.05 (17)	C8—C7—H7	119.7
C10—C9—O1	120.70 (17)	C6—C7—H7	119.7
C3—C4—C5	120.02 (17)	N2—C2—C3	179.7 (3)
C3—C4—H4	120.0	C5—C6—C7	119.60 (18)
C5—C4—H4	120.0	C5—C6—H6	120.2
C14—C13—C12	121.81 (17)	C7—C6—H6	120.2
C14—C13—H13	119.1	N3—C25—C23	178.0 (2)
C12—C13—H13	119.1	N4—C26—C22	178.8 (2)
C11—C10—C9	119.31 (18)	C20—C21—C22	120.65 (18)
C11—C10—H10	120.3	C20—C21—H21	119.7
C9—C10—H10	120.3	C22—C21—H21	119.7
C6—C5—O1	125.34 (17)	C19—C20—C21	119.39 (19)
C6—C5—C4	120.46 (17)	C19—C20—H20	120.3
O1—C5—C4	114.19 (16)	C21—C20—H20	120.3
C10—C11—C12	121.22 (18)	N1—C1—C8	178.7 (2)
C9—C18—C17—C12	−0.3 (2)	C4—C3—C8—C7	0.4 (3)
C9—C18—C17—C16	−178.12 (16)	C2—C3—C8—C7	−179.00 (17)
C11—C12—C17—C18	3.0 (2)	C4—C3—C8—C1	−177.84 (17)
C13—C12—C17—C18	−176.83 (16)	C2—C3—C8—C1	2.8 (3)
C11—C12—C17—C16	−179.11 (15)	C15—O2—C19—C20	−41.7 (2)
C13—C12—C17—C16	1.1 (2)	C15—O2—C19—C24	144.79 (16)
C15—C16—C17—C18	176.79 (17)	C23—C24—C19—O2	171.54 (15)
C15—C16—C17—C12	−1.0 (2)	C23—C24—C19—C20	−2.1 (3)
C17—C16—C15—O2	−174.35 (15)	C19—C24—C23—C22	0.8 (2)
C17—C16—C15—C14	0.1 (3)	C19—C24—C23—C25	−176.66 (16)
C19—O2—C15—C16	−35.8 (3)	C24—C23—C22—C21	1.1 (3)
C19—O2—C15—C14	149.36 (16)	C25—C23—C22—C21	178.54 (17)
C16—C15—C14—C13	0.9 (3)	C24—C23—C22—C26	−176.49 (16)
O2—C15—C14—C13	175.78 (15)	C25—C23—C22—C26	0.9 (3)
C17—C18—C9—C10	−3.2 (3)	C3—C8—C7—C6	0.6 (3)
C17—C18—C9—O1	−177.79 (15)	C1—C8—C7—C6	178.75 (18)
C5—O1—C9—C18	−127.47 (18)	C4—C3—C2—N2	−159 (100)
C5—O1—C9—C10	57.8 (2)	C8—C3—C2—N2	20 (51)
C15—C14—C13—C12	−0.8 (3)	O1—C5—C6—C7	179.31 (17)
C11—C12—C13—C14	−179.95 (16)	C4—C5—C6—C7	0.7 (3)
C17—C12—C13—C14	−0.1 (3)	C8—C7—C6—C5	−1.1 (3)
C18—C9—C10—C11	3.9 (3)	C24—C23—C25—N3	78 (6)
O1—C9—C10—C11	178.30 (16)	C22—C23—C25—N3	−100 (6)
C9—O1—C5—C6	0.3 (3)	C21—C22—C26—N4	−69 (13)
C9—O1—C5—C4	179.06 (16)	C23—C22—C26—N4	109 (13)
C3—C4—C5—C6	0.3 (3)	C23—C22—C21—C20	−1.8 (3)
C3—C4—C5—O1	−178.52 (16)	C26—C22—C21—C20	175.79 (17)
C9—C10—C11—C12	−1.0 (3)	O2—C19—C20—C21	−171.75 (16)
C13—C12—C11—C10	177.48 (17)	C24—C19—C20—C21	1.4 (3)
C17—C12—C11—C10	−2.4 (3)	C22—C21—C20—C19	0.6 (3)
C5—C4—C3—C8	−0.8 (3)	C7—C8—C1—N1	−160 (11)
C5—C4—C3—C2	178.58 (17)	C3—C8—C1—N1	18 (11)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···N4^i	0.93	2.56	3.397 (2)	151
C7—H7···N3^ii	0.93	2.62	3.486 (3)	155

Symmetry codes: (i) −x+1, −y, −z; (ii) x+1/2, −y−1/2, z+1/2.