4,5-Bis(1-naphthoxy)­phthalo­nitrile

In the title mol­ecule, C₂₈H₁₆N₂O₂, the dihedral angles between the planes of the two naphthalene moieties and the benzene ring are 84.78 (9) and 76.66 (9)°. The molecular structure is influenced by C—H...O and C—H...π interactions and the crystal structure is stabilized by π–π interactions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.035
• wR factor = 0.069
• Data-to-parameter ratio = 10.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         47 Perc.
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.80 mm
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C12    -   C13      =       6.84 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C23    -   C28      =       5.32 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C26    -   C27      =       5.43 su
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C3     -   C6       =       1.44 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C4     -   C7       =       1.44 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   7 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
   5 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

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Computing details

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 1990); software used to prepare material for publication: WinGX (Farrugia, 1999).

4,5-Bis(1-naphthoxy)phthalonitrile

Crystal data

C28H16N2O2	Z = 2
Mr = 412.43	F(000) = 428
Triclinic, P1	Dx = 1.338 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.9667 (14) Å	Cell parameters from 5492 reflections
b = 10.4946 (15) Å	θ = 2.1–29.5°
c = 11.2637 (16) Å	µ = 0.09 mm^−1
α = 116.931 (11)°	T = 293 K
β = 99.441 (11)°	Plate, brown
γ = 93.570 (12)°	0.80 × 0.35 × 0.03 mm
V = 1023.6 (3) Å^3

Data collection

Stoe IPDS 2 diffractometer	1694 reflections with I > 2σ(I)
Radiation source: sealed X-ray tube	Rint = 0.090
Plane graphite monochromator	θmax = 25.0°, θmin = 2.1°
Detector resolution: 6.67 pixels mm^-1	h = −11→11
φ scans	k = −12→12
13294 measured reflections	l = −13→13
3606 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)] = 0.035	All H-atom parameters refined
wR(F^2) = 0.069	w = 1/[σ^2(Fo^2) + (0.0125P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.80	(Δ/σ)max = 0.001
3606 reflections	Δρmax = 0.18 e Å^−3
354 parameters	Δρmin = −0.15 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: 0.0086 (10)

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	0.49340 (14)	0.74607 (14)	0.05429 (13)	0.0515 (4)
O2	0.68250 (14)	0.73471 (14)	0.24528 (14)	0.0570 (4)
N1	0.0331 (2)	0.4099 (2)	0.0951 (2)	0.0783 (7)
N2	0.3128 (2)	0.4235 (2)	0.4124 (2)	0.0856 (7)
C1	0.4542 (2)	0.6767 (2)	0.1247 (2)	0.0462 (5)
C2	0.3205 (2)	0.6088 (2)	0.0916 (2)	0.0484 (6)
C3	0.2824 (2)	0.53677 (19)	0.1609 (2)	0.0476 (6)
C4	0.3782 (2)	0.53688 (19)	0.2657 (2)	0.0469 (5)
C5	0.5139 (2)	0.6031 (2)	0.2981 (2)	0.0495 (6)
C6	0.1432 (3)	0.4648 (2)	0.1256 (2)	0.0594 (6)
C7	0.3379 (2)	0.4710 (2)	0.3449 (2)	0.0575 (6)
C8	0.5520 (2)	0.67022 (19)	0.2256 (2)	0.0461 (5)
C9	0.5321 (2)	0.8979 (2)	0.1315 (2)	0.0472 (6)
C10	0.4707 (3)	0.9800 (3)	0.2325 (3)	0.0597 (7)
C11	0.5131 (3)	1.1311 (3)	0.3027 (3)	0.0717 (8)
C12	0.6118 (3)	1.1931 (3)	0.2671 (3)	0.0669 (8)
C13	0.6744 (2)	1.1090 (2)	0.1608 (2)	0.0510 (6)
C14	0.6360 (2)	0.9574 (2)	0.0909 (2)	0.0445 (5)
C15	0.6994 (2)	0.8740 (3)	−0.0135 (2)	0.0555 (6)
C16	0.7986 (3)	0.9372 (3)	−0.0503 (3)	0.0692 (7)
C17	0.8361 (3)	1.0876 (3)	0.0190 (3)	0.0748 (8)
C18	0.7778 (3)	1.1712 (3)	0.1213 (3)	0.0668 (8)
C19	0.7855 (2)	0.7367 (2)	0.3483 (2)	0.0498 (6)
C20	0.8495 (2)	0.6190 (3)	0.3210 (3)	0.0624 (7)
C21	0.9568 (3)	0.6250 (3)	0.4212 (3)	0.0706 (8)
C22	0.9975 (3)	0.7458 (3)	0.5419 (3)	0.0683 (8)
C23	0.9328 (2)	0.8701 (2)	0.5708 (2)	0.0542 (6)
C24	0.8232 (2)	0.8648 (2)	0.4706 (2)	0.0485 (6)
C25	0.7611 (3)	0.9889 (3)	0.4968 (3)	0.0621 (7)
C26	0.8075 (3)	1.1115 (3)	0.6154 (3)	0.0763 (8)
C27	0.9148 (4)	1.1178 (3)	0.7154 (3)	0.0854 (9)
C28	0.9749 (3)	0.9996 (3)	0.6929 (3)	0.0746 (8)
H2	0.259 (2)	0.6063 (18)	0.0161 (19)	0.052 (6)*
H5	0.5742 (19)	0.6033 (17)	0.3686 (18)	0.044 (6)*
H10	0.401 (2)	0.940 (2)	0.261 (2)	0.080 (8)*
H11	0.467 (2)	1.184 (2)	0.369 (2)	0.076 (9)*
H12	0.637 (2)	1.296 (2)	0.315 (2)	0.084 (8)*
H15	0.671 (2)	0.769 (2)	−0.0599 (19)	0.062 (6)*
H16	0.836 (3)	0.876 (3)	−0.131 (3)	0.107 (10)*
H17	0.903 (3)	1.135 (3)	−0.005 (3)	0.113 (10)*
H18	0.801 (2)	1.273 (2)	0.166 (2)	0.067 (7)*
H20	0.822 (2)	0.529 (2)	0.226 (2)	0.085 (7)*
H21	0.993 (3)	0.540 (2)	0.400 (2)	0.089 (9)*
H22	1.062 (2)	0.756 (2)	0.611 (2)	0.064 (7)*
H25	0.700 (2)	0.986 (2)	0.429 (2)	0.072 (8)*
H26	0.761 (3)	1.192 (3)	0.622 (3)	0.109 (11)*
H27	0.950 (3)	1.206 (3)	0.792 (2)	0.090 (8)*
H28	1.045 (3)	0.999 (2)	0.753 (2)	0.084 (9)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0586 (10)	0.0491 (9)	0.0480 (9)	−0.0042 (7)	0.0007 (7)	0.0289 (7)
O2	0.0465 (10)	0.0669 (10)	0.0621 (10)	−0.0082 (7)	−0.0046 (8)	0.0417 (8)
N1	0.0576 (14)	0.0731 (14)	0.1016 (17)	−0.0088 (11)	0.0069 (12)	0.0445 (12)
N2	0.0949 (17)	0.0954 (16)	0.0957 (16)	0.0100 (12)	0.0330 (14)	0.0661 (14)
C1	0.0499 (14)	0.0439 (12)	0.0451 (12)	−0.0003 (10)	0.0023 (11)	0.0248 (10)
C2	0.0506 (15)	0.0437 (12)	0.0457 (13)	0.0007 (11)	−0.0022 (12)	0.0217 (11)
C3	0.0494 (14)	0.0372 (11)	0.0504 (13)	0.0007 (10)	0.0079 (11)	0.0174 (10)
C4	0.0523 (15)	0.0405 (12)	0.0490 (13)	0.0014 (10)	0.0095 (12)	0.0233 (10)
C5	0.0535 (16)	0.0486 (13)	0.0492 (14)	0.0037 (11)	0.0019 (12)	0.0290 (12)
C6	0.0570 (16)	0.0466 (13)	0.0707 (17)	−0.0002 (12)	0.0094 (14)	0.0267 (12)
C7	0.0604 (16)	0.0561 (14)	0.0618 (15)	0.0066 (11)	0.0165 (13)	0.0319 (13)
C8	0.0438 (14)	0.0435 (12)	0.0489 (13)	0.0002 (10)	0.0020 (11)	0.0235 (10)
C9	0.0468 (14)	0.0431 (12)	0.0508 (13)	0.0039 (11)	−0.0028 (12)	0.0262 (11)
C10	0.0592 (17)	0.0633 (17)	0.0649 (17)	0.0135 (14)	0.0174 (14)	0.0356 (14)
C11	0.081 (2)	0.0579 (18)	0.0737 (19)	0.0294 (16)	0.0189 (17)	0.0260 (15)
C12	0.075 (2)	0.0452 (16)	0.0741 (19)	0.0097 (14)	−0.0028 (16)	0.0290 (15)
C13	0.0537 (15)	0.0444 (13)	0.0526 (14)	0.0022 (12)	−0.0057 (12)	0.0271 (12)
C14	0.0400 (13)	0.0458 (13)	0.0503 (13)	0.0018 (10)	−0.0032 (11)	0.0296 (11)
C15	0.0545 (16)	0.0571 (16)	0.0574 (16)	0.0044 (13)	0.0070 (13)	0.0312 (14)
C16	0.0652 (18)	0.0792 (19)	0.0687 (18)	0.0017 (15)	0.0135 (15)	0.0410 (16)
C17	0.066 (2)	0.081 (2)	0.082 (2)	−0.0123 (16)	0.0019 (17)	0.0503 (18)
C18	0.0666 (18)	0.0530 (17)	0.0779 (19)	−0.0105 (15)	−0.0121 (16)	0.0399 (16)
C19	0.0407 (13)	0.0593 (14)	0.0539 (14)	−0.0010 (11)	0.0015 (11)	0.0345 (12)
C20	0.0662 (17)	0.0551 (15)	0.0640 (17)	0.0061 (13)	0.0040 (14)	0.0299 (14)
C21	0.0711 (19)	0.0656 (18)	0.081 (2)	0.0193 (15)	0.0093 (16)	0.0411 (17)
C22	0.0524 (17)	0.088 (2)	0.0697 (19)	0.0077 (15)	−0.0021 (15)	0.0472 (17)
C23	0.0467 (14)	0.0628 (15)	0.0505 (14)	−0.0069 (12)	0.0031 (12)	0.0288 (12)
C24	0.0421 (13)	0.0555 (14)	0.0503 (13)	0.0009 (11)	0.0110 (11)	0.0274 (12)
C25	0.0624 (18)	0.0632 (17)	0.0654 (18)	0.0099 (14)	0.0205 (15)	0.0320 (15)
C26	0.093 (2)	0.068 (2)	0.069 (2)	0.0127 (17)	0.0336 (18)	0.0278 (18)
C27	0.108 (3)	0.071 (2)	0.0592 (19)	−0.013 (2)	0.0270 (19)	0.0155 (17)
C28	0.070 (2)	0.088 (2)	0.0568 (18)	−0.0106 (17)	0.0057 (16)	0.0324 (17)

Geometric parameters (Å, º)

O1—C1	1.379 (2)	C14—C15	1.389 (3)
O1—C9	1.415 (2)	C15—C16	1.375 (3)
O2—C8	1.363 (2)	C15—H15	0.976 (18)
O2—C19	1.409 (2)	C16—C17	1.398 (3)
N1—C6	1.128 (3)	C16—H16	0.99 (2)
N2—C7	1.130 (3)	C17—C18	1.343 (3)
C1—C2	1.378 (3)	C17—H17	0.95 (3)
C1—C8	1.401 (3)	C18—H18	0.948 (19)
C2—C3	1.386 (3)	C19—C20	1.358 (3)
C2—H2	0.951 (19)	C19—C24	1.391 (3)
C3—C4	1.391 (3)	C20—C21	1.397 (3)
C3—C6	1.439 (3)	C20—H20	1.03 (2)
C4—C5	1.391 (3)	C21—C22	1.347 (3)
C4—C7	1.441 (3)	C21—H21	0.92 (2)
C5—C8	1.377 (3)	C22—C23	1.419 (3)
C5—H5	0.913 (18)	C22—H22	0.88 (2)
C9—C10	1.348 (3)	C23—C28	1.401 (3)
C9—C14	1.416 (3)	C23—C24	1.414 (3)
C10—C11	1.410 (3)	C24—C25	1.407 (3)
C10—H10	0.96 (2)	C25—C26	1.349 (3)
C11—C12	1.356 (3)	C25—H25	0.88 (2)
C11—H11	0.92 (2)	C26—C27	1.395 (4)
C12—C13	1.400 (3)	C26—H26	0.97 (3)
C12—H12	0.95 (2)	C27—C28	1.349 (4)
C13—C14	1.410 (3)	C27—H27	0.93 (2)
C13—C18	1.420 (3)	C28—H28	0.90 (2)
C1—O1—C9	115.68 (15)	C16—C15—H15	121.5 (12)
C8—O2—C19	118.56 (15)	C14—C15—H15	117.6 (12)
C2—C1—O1	119.98 (18)	C15—C16—C17	119.3 (3)
C2—C1—C8	120.2 (2)	C15—C16—H16	119.1 (15)
O1—C1—C8	119.72 (18)	C17—C16—H16	121.4 (15)
C1—C2—C3	119.7 (2)	C18—C17—C16	121.2 (3)
C1—C2—H2	118.1 (11)	C18—C17—H17	117.3 (16)
C3—C2—H2	121.9 (11)	C16—C17—H17	121.4 (16)
C2—C3—C4	119.76 (19)	C17—C18—C13	120.7 (3)
C2—C3—C6	119.7 (2)	C17—C18—H18	121.1 (13)
C4—C3—C6	120.5 (2)	C13—C18—H18	118.2 (13)
C3—C4—C5	120.8 (2)	C20—C19—C24	123.2 (2)
C3—C4—C7	120.47 (19)	C20—C19—O2	119.2 (2)
C5—C4—C7	118.71 (19)	C24—C19—O2	117.4 (2)
C8—C5—C4	119.0 (2)	C19—C20—C21	118.8 (2)
C8—C5—H5	122.0 (11)	C19—C20—H20	120.3 (13)
C4—C5—H5	119.0 (11)	C21—C20—H20	120.8 (13)
N1—C6—C3	177.9 (3)	C22—C21—C20	120.7 (3)
N2—C7—C4	176.1 (3)	C22—C21—H21	124.1 (15)
O2—C8—C5	124.25 (19)	C20—C21—H21	115.2 (15)
O2—C8—C1	115.39 (18)	C21—C22—C23	121.0 (3)
C5—C8—C1	120.4 (2)	C21—C22—H22	125.4 (13)
C10—C9—O1	122.4 (2)	C23—C22—H22	113.5 (13)
C10—C9—C14	122.7 (2)	C28—C23—C24	118.3 (3)
O1—C9—C14	114.9 (2)	C28—C23—C22	122.9 (3)
C9—C10—C11	118.9 (3)	C24—C23—C22	118.8 (2)
C9—C10—H10	123.0 (13)	C19—C24—C25	123.3 (2)
C11—C10—H10	118.1 (13)	C19—C24—C23	117.5 (2)
C12—C11—C10	120.5 (3)	C25—C24—C23	119.1 (2)
C12—C11—H11	123.0 (14)	C26—C25—C24	120.0 (3)
C10—C11—H11	116.4 (14)	C26—C25—H25	122.6 (14)
C11—C12—C13	120.9 (2)	C24—C25—H25	116.9 (14)
C11—C12—H12	118.5 (14)	C25—C26—C27	121.4 (3)
C13—C12—H12	120.6 (14)	C25—C26—H26	113.6 (17)
C12—C13—C14	119.7 (2)	C27—C26—H26	125.0 (17)
C12—C13—C18	122.1 (2)	C28—C27—C26	119.5 (3)
C14—C13—C18	118.2 (3)	C28—C27—H27	121.0 (17)
C15—C14—C13	119.6 (2)	C26—C27—H27	119.2 (16)
C15—C14—C9	123.18 (19)	C27—C28—C23	121.6 (3)
C13—C14—C9	117.2 (2)	C27—C28—H28	123.0 (15)
C16—C15—C14	121.0 (2)	C23—C28—H28	115.4 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···O1	0.98 (2)	2.41 (2)	2.775 (3)	101 (1)
C25—H25···O2	0.88 (2)	2.48 (2)	2.815 (3)	103 (2)
C25—H25···Cg2	0.88 (2)	3.04 (2)	3.882 (3)	160 (2)
C26—H26···Cg1^i	0.97 (3)	3.10 (3)	3.879 (3)	138 (2)
C28—H28···Cg3^ii	0.90 (2)	2.90 (2)	3.793 (3)	176 (2)

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