The molecule of the title compound, 4,4′-naphthalene-2,7-dioxydibenzene-1,2-dicarbonitrile, C
26H
12N
4O
2, 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.
Supporting information
CCDC reference: 236103
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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
top
Crystal data top
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) Å3 | 0.50 × 0.31 × 0.07 mm |
Z = 4 | |
Data collection top
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 top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.036 | H-atom parameters constrained |
wR(F2) = 0.084 | w = 1/[σ2(Fo2) + (0.0424P)2] where P = (Fo2 + 2Fc2)/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+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0097 (8) |
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 | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
D—H···A | D—H | H···A | D···A | D—H···A |
C16—H16···N4i | 0.93 | 2.56 | 3.397 (2) | 151 |
C7—H7···N3ii | 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. |