Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807049495/ci2482sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807049495/ci2482Isup2.hkl |
CCDC reference: 667345
Key indicators
- Single-crystal X-ray study
- T = 153 K
- Mean (C-C) = 0.002 Å
- R factor = 0.039
- wR factor = 0.136
- Data-to-parameter ratio = 16.8
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for C24 - C25 .. 8.64 su
Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.22 Ratio
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 1 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 2 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For applications of 1,4-naphthalenedicarboxylic acid derivatives, see: Fukuzumi et al. (1994) and Tsukada et al. (1994). For related structures, see: Jing, Qin, Gu, Zhang & Lei (2006); Jing, Qin, Gu, Zhang & Mao (2006).
Naphthalene-1,4-dicarboxylic acid (2 mmol) and an excess of thionyl chloride (6 mmol) in dioxane (20 ml) were boiled under reflux for 6 h. The solution was distilled under reduced pressure and a yellow solid was formed. N-Methyl phenylamine (4 mmol) in tetrahydrofuran (20 ml) was added to the yellow solid and boiled under reflux for 1 d. The solution was then cooled to ambient temperature and filtered to remove the tetrahydrofuran. The precipitate was dissolved in dimethylsulfoxide and allowed to stand for one month at ambient temperature, after which time white single crystals of (I) suitable for X-ray diffraction were obtained.
All H atoms were placed in calculated positions, with C—H = 0.95 or 0.98 Å, and refined using a riding model, with Uiso(H) = 1.2Ueq(C). The methyl groups were allowed to rotate but not to tip.
1,4-Naphthalenedicarboxylic acid derivatives are a class of intermediates important for applications as monomers in the preparation of polymers (Fukuzumi et al., 1994; Tsukada et al., 1994). Previously, we have reported the crystal structures of N,N'-bis(4-nitrophenyl)naphthalene-1,4-dicarboxamide dimethylsulfoxide disolvate (Jing, Qin, Gu, Zhang & Mao, 2006) and N,N'-bis(2-methoxyphenyl)naphthalene-1,4-dicarboxamide (Jing, Qin, Gu, Zhang & Lei, 2006). We now report the crystal structure of the title compound, (I).
The bond lengths and angles in (I) are normal. The naphthalene ring system is planar, with a maximum deviation of 0.017 (1) Å for atom C2. As a result of steric effects, two amide groups (O1/N1/C1/C11 and O2/N2/C4/C19) are twisted away from the naphthalene mean plane by 63.94 (3) and 66.07 (3)°, respectively (Fig. 1). The dihedral angle between the O1/N1/C1/C11 and C13—C18 planes is 65.80 (5)°, and that between the O2/N2/C4/C19 and C21—C26 planes is 56.36 (6)°. The crystal packing is stabilized by intermolecular C—H···π interactions involving the C21—C26 phenyl ring (centroid Cg1; Table 1).
For applications of 1,4-naphthalenedicarboxylic acid derivatives, see: Fukuzumi et al. (1994) and Tsukada et al. (1994). For related structures, see: Jing, Qin, Gu, Zhang & Lei (2006); Jing, Qin, Gu, Zhang & Mao (2006).
Data collection: RAPID-AUTO (Rigaku/MSC, 2004); cell refinement: RAPID-AUTO (Rigaku/MSC, 2004); data reduction: RAPID-AUTO (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
Fig. 1. The molecular structure of (I), showing 30% probability displacement ellipsoids. |
C26H22N2O2 | Z = 2 |
Mr = 394.46 | F(000) = 416 |
Triclinic, P1 | Dx = 1.296 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.9970 (6) Å | Cell parameters from 7714 reflections |
b = 9.3627 (5) Å | θ = 3.1–27.5° |
c = 13.5538 (7) Å | µ = 0.08 mm−1 |
α = 105.329 (1)° | T = 153 K |
β = 92.391 (2)° | Block, colourless |
γ = 111.656 (2)° | 0.55 × 0.33 × 0.21 mm |
V = 1010.95 (10) Å3 |
Rigaku R-AXIS RAPID diffractometer | 3695 reflections with I > 2σ(I) |
Radiation source: Rotating Anode | Rint = 0.017 |
Graphite monochromator | θmax = 27.5°, θmin = 3.1° |
ω scans | h = −11→11 |
9974 measured reflections | k = −12→12 |
4593 independent reflections | l = −15→17 |
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)] = 0.039 | H-atom parameters constrained |
wR(F2) = 0.136 | w = 1/[σ2(Fo2) + (0.0828P)2 + 0.279P] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max = 0.001 |
4593 reflections | Δρmax = 0.35 e Å−3 |
274 parameters | Δρmin = −0.26 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.017 (4) |
C26H22N2O2 | γ = 111.656 (2)° |
Mr = 394.46 | V = 1010.95 (10) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.9970 (6) Å | Mo Kα radiation |
b = 9.3627 (5) Å | µ = 0.08 mm−1 |
c = 13.5538 (7) Å | T = 153 K |
α = 105.329 (1)° | 0.55 × 0.33 × 0.21 mm |
β = 92.391 (2)° |
Rigaku R-AXIS RAPID diffractometer | 3695 reflections with I > 2σ(I) |
9974 measured reflections | Rint = 0.017 |
4593 independent reflections |
R[F2 > 2σ(F2)] = 0.039 | 0 restraints |
wR(F2) = 0.136 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.35 e Å−3 |
4593 reflections | Δρmin = −0.26 e Å−3 |
274 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.78271 (13) | 0.56379 (13) | −0.00270 (8) | 0.0238 (2) | |
N2 | 0.77994 (13) | 0.57326 (13) | 0.52950 (8) | 0.0258 (3) | |
O1 | 0.80460 (13) | 0.32300 (11) | −0.03540 (7) | 0.0323 (2) | |
O2 | 0.81029 (13) | 0.33566 (11) | 0.47733 (7) | 0.0320 (2) | |
C1 | 0.78108 (15) | 0.44480 (14) | 0.13806 (9) | 0.0211 (3) | |
C2 | 0.90138 (15) | 0.56211 (14) | 0.21448 (10) | 0.0232 (3) | |
H2 | 0.9872 | 0.6429 | 0.1971 | 0.028* | |
C3 | 0.89866 (15) | 0.56371 (14) | 0.31845 (10) | 0.0234 (3) | |
H3 | 0.9834 | 0.6451 | 0.3706 | 0.028* | |
C4 | 0.77506 (15) | 0.44910 (14) | 0.34541 (9) | 0.0208 (3) | |
C5 | 0.51417 (15) | 0.20772 (15) | 0.29354 (10) | 0.0239 (3) | |
H5 | 0.5098 | 0.2092 | 0.3637 | 0.029* | |
C6 | 0.39271 (16) | 0.09150 (15) | 0.21772 (11) | 0.0281 (3) | |
H6 | 0.3048 | 0.0133 | 0.2356 | 0.034* | |
C7 | 0.39727 (16) | 0.08714 (16) | 0.11339 (11) | 0.0281 (3) | |
H7 | 0.3130 | 0.0054 | 0.0612 | 0.034* | |
C8 | 0.52240 (15) | 0.19998 (15) | 0.08664 (10) | 0.0239 (3) | |
H8 | 0.5236 | 0.1956 | 0.0159 | 0.029* | |
C9 | 0.65017 (14) | 0.32318 (14) | 0.16274 (9) | 0.0201 (3) | |
C10 | 0.64688 (14) | 0.32649 (13) | 0.26882 (9) | 0.0196 (3) | |
C11 | 0.79059 (15) | 0.43809 (15) | 0.02613 (10) | 0.0228 (3) | |
C12 | 0.79649 (18) | 0.56323 (18) | −0.11009 (10) | 0.0314 (3) | |
H12A | 0.9103 | 0.6186 | −0.1159 | 0.038* | |
H12B | 0.7331 | 0.6190 | −0.1308 | 0.038* | |
H12C | 0.7552 | 0.4518 | −0.1554 | 0.038* | |
C13 | 0.78233 (16) | 0.70820 (15) | 0.06758 (10) | 0.0233 (3) | |
C14 | 0.64906 (17) | 0.70588 (17) | 0.11556 (10) | 0.0292 (3) | |
H14 | 0.5575 | 0.6077 | 0.1038 | 0.035* | |
C15 | 0.6503 (2) | 0.84799 (19) | 0.18088 (12) | 0.0372 (4) | |
H15 | 0.5594 | 0.8469 | 0.2143 | 0.045* | |
C16 | 0.7831 (2) | 0.99164 (19) | 0.19777 (12) | 0.0420 (4) | |
H16 | 0.7832 | 1.0887 | 0.2426 | 0.050* | |
C17 | 0.9154 (2) | 0.99328 (18) | 0.14922 (13) | 0.0421 (4) | |
H17 | 1.0064 | 1.0918 | 0.1606 | 0.050* | |
C18 | 0.91587 (18) | 0.85181 (16) | 0.08391 (11) | 0.0324 (3) | |
H18 | 1.0070 | 0.8531 | 0.0506 | 0.039* | |
C19 | 0.78729 (15) | 0.44667 (15) | 0.45572 (9) | 0.0230 (3) | |
C20 | 0.81888 (19) | 0.5865 (2) | 0.63851 (10) | 0.0377 (4) | |
H20A | 0.7882 | 0.4784 | 0.6460 | 0.045* | |
H20B | 0.7591 | 0.6420 | 0.6806 | 0.045* | |
H20C | 0.9354 | 0.6478 | 0.6618 | 0.045* | |
C21 | 0.74327 (16) | 0.69856 (15) | 0.50824 (10) | 0.0265 (3) | |
C22 | 0.60438 (17) | 0.66366 (17) | 0.44191 (11) | 0.0298 (3) | |
H22 | 0.5337 | 0.5546 | 0.4088 | 0.036* | |
C23 | 0.5681 (2) | 0.7869 (2) | 0.42367 (14) | 0.0452 (4) | |
H23 | 0.4733 | 0.7616 | 0.3776 | 0.054* | |
C24 | 0.6678 (3) | 0.9448 (2) | 0.47155 (18) | 0.0592 (6) | |
H24 | 0.6428 | 1.0288 | 0.4584 | 0.071* | |
C25 | 0.8031 (3) | 0.98039 (19) | 0.53825 (18) | 0.0631 (7) | |
H25 | 0.8711 | 1.0900 | 0.5720 | 0.076* | |
C26 | 0.8442 (2) | 0.85844 (18) | 0.55828 (14) | 0.0451 (4) | |
H26 | 0.9387 | 0.8848 | 0.6049 | 0.054* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0268 (5) | 0.0250 (5) | 0.0212 (5) | 0.0105 (4) | 0.0082 (4) | 0.0084 (4) |
N2 | 0.0271 (6) | 0.0300 (6) | 0.0192 (5) | 0.0122 (4) | 0.0031 (4) | 0.0043 (4) |
O1 | 0.0445 (6) | 0.0268 (5) | 0.0272 (5) | 0.0163 (4) | 0.0127 (4) | 0.0067 (4) |
O2 | 0.0407 (6) | 0.0317 (5) | 0.0287 (5) | 0.0183 (4) | 0.0022 (4) | 0.0120 (4) |
C1 | 0.0233 (6) | 0.0218 (6) | 0.0223 (6) | 0.0123 (5) | 0.0060 (5) | 0.0080 (5) |
C2 | 0.0218 (6) | 0.0202 (6) | 0.0272 (6) | 0.0072 (5) | 0.0056 (5) | 0.0080 (5) |
C3 | 0.0223 (6) | 0.0195 (6) | 0.0259 (6) | 0.0079 (5) | 0.0019 (5) | 0.0039 (5) |
C4 | 0.0237 (6) | 0.0199 (6) | 0.0214 (6) | 0.0119 (5) | 0.0041 (5) | 0.0055 (5) |
C5 | 0.0258 (6) | 0.0238 (6) | 0.0238 (6) | 0.0108 (5) | 0.0081 (5) | 0.0077 (5) |
C6 | 0.0239 (6) | 0.0236 (6) | 0.0331 (7) | 0.0059 (5) | 0.0086 (5) | 0.0072 (5) |
C7 | 0.0230 (6) | 0.0245 (6) | 0.0297 (7) | 0.0062 (5) | 0.0010 (5) | 0.0017 (5) |
C8 | 0.0255 (6) | 0.0247 (6) | 0.0209 (6) | 0.0112 (5) | 0.0024 (5) | 0.0040 (5) |
C9 | 0.0208 (6) | 0.0195 (6) | 0.0219 (6) | 0.0107 (5) | 0.0044 (5) | 0.0053 (5) |
C10 | 0.0211 (6) | 0.0184 (5) | 0.0213 (6) | 0.0107 (4) | 0.0043 (4) | 0.0047 (4) |
C11 | 0.0210 (6) | 0.0240 (6) | 0.0220 (6) | 0.0073 (5) | 0.0049 (5) | 0.0066 (5) |
C12 | 0.0402 (8) | 0.0383 (7) | 0.0225 (6) | 0.0190 (6) | 0.0121 (6) | 0.0139 (6) |
C13 | 0.0280 (6) | 0.0251 (6) | 0.0216 (6) | 0.0136 (5) | 0.0045 (5) | 0.0103 (5) |
C14 | 0.0290 (7) | 0.0358 (7) | 0.0278 (7) | 0.0162 (6) | 0.0065 (5) | 0.0123 (6) |
C15 | 0.0438 (8) | 0.0498 (9) | 0.0317 (7) | 0.0327 (7) | 0.0111 (6) | 0.0128 (7) |
C16 | 0.0638 (11) | 0.0347 (8) | 0.0360 (8) | 0.0318 (8) | 0.0044 (7) | 0.0065 (6) |
C17 | 0.0513 (10) | 0.0259 (7) | 0.0440 (9) | 0.0114 (6) | 0.0032 (7) | 0.0086 (6) |
C18 | 0.0334 (7) | 0.0295 (7) | 0.0339 (7) | 0.0103 (6) | 0.0088 (6) | 0.0116 (6) |
C19 | 0.0212 (6) | 0.0252 (6) | 0.0215 (6) | 0.0085 (5) | 0.0017 (5) | 0.0065 (5) |
C20 | 0.0412 (8) | 0.0539 (9) | 0.0185 (6) | 0.0246 (7) | 0.0008 (6) | 0.0037 (6) |
C21 | 0.0293 (7) | 0.0229 (6) | 0.0264 (6) | 0.0097 (5) | 0.0135 (5) | 0.0054 (5) |
C22 | 0.0354 (7) | 0.0320 (7) | 0.0303 (7) | 0.0181 (6) | 0.0141 (6) | 0.0139 (6) |
C23 | 0.0608 (11) | 0.0530 (10) | 0.0519 (10) | 0.0407 (9) | 0.0329 (8) | 0.0335 (8) |
C24 | 0.0801 (15) | 0.0446 (10) | 0.0856 (15) | 0.0423 (10) | 0.0564 (13) | 0.0394 (10) |
C25 | 0.0787 (15) | 0.0202 (7) | 0.0832 (15) | 0.0115 (8) | 0.0504 (13) | 0.0100 (8) |
C26 | 0.0413 (9) | 0.0280 (7) | 0.0492 (9) | 0.0028 (6) | 0.0187 (7) | −0.0013 (7) |
N1—C11 | 1.3583 (16) | C12—H12B | 0.98 |
N1—C13 | 1.4347 (16) | C12—H12C | 0.98 |
N1—C12 | 1.4647 (16) | C13—C14 | 1.3836 (19) |
N2—C19 | 1.3587 (16) | C13—C18 | 1.3887 (18) |
N2—C21 | 1.4229 (17) | C14—C15 | 1.385 (2) |
N2—C20 | 1.4660 (17) | C14—H14 | 0.95 |
O1—C11 | 1.2273 (16) | C15—C16 | 1.384 (2) |
O2—C19 | 1.2343 (15) | C15—H15 | 0.95 |
C1—C2 | 1.3704 (17) | C16—C17 | 1.381 (3) |
C1—C9 | 1.4283 (16) | C16—H16 | 0.95 |
C1—C11 | 1.5091 (17) | C17—C18 | 1.387 (2) |
C2—C3 | 1.4067 (18) | C17—H17 | 0.95 |
C2—H2 | 0.95 | C18—H18 | 0.95 |
C3—C4 | 1.3719 (17) | C20—H20A | 0.98 |
C3—H3 | 0.95 | C20—H20B | 0.98 |
C4—C10 | 1.4207 (16) | C20—H20C | 0.98 |
C4—C19 | 1.5014 (17) | C21—C22 | 1.388 (2) |
C5—C6 | 1.3681 (18) | C21—C26 | 1.3906 (19) |
C5—C10 | 1.4230 (17) | C22—C23 | 1.386 (2) |
C5—H5 | 0.95 | C22—H22 | 0.95 |
C6—C7 | 1.4066 (19) | C23—C24 | 1.370 (3) |
C6—H6 | 0.95 | C23—H23 | 0.95 |
C7—C8 | 1.3688 (18) | C24—C25 | 1.364 (3) |
C7—H7 | 0.95 | C24—H24 | 0.95 |
C8—C9 | 1.4174 (17) | C25—C26 | 1.408 (3) |
C8—H8 | 0.95 | C25—H25 | 0.95 |
C9—C10 | 1.4317 (17) | C26—H26 | 0.95 |
C12—H12A | 0.98 | ||
C11—N1—C13 | 124.44 (10) | C14—C13—C18 | 120.41 (12) |
C11—N1—C12 | 118.52 (11) | C14—C13—N1 | 120.69 (11) |
C13—N1—C12 | 116.55 (10) | C18—C13—N1 | 118.86 (12) |
C19—N2—C21 | 124.32 (11) | C13—C14—C15 | 119.45 (13) |
C19—N2—C20 | 118.31 (11) | C13—C14—H14 | 120.3 |
C21—N2—C20 | 117.32 (11) | C15—C14—H14 | 120.3 |
C2—C1—C9 | 120.60 (11) | C16—C15—C14 | 120.51 (14) |
C2—C1—C11 | 120.02 (11) | C16—C15—H15 | 119.7 |
C9—C1—C11 | 119.30 (11) | C14—C15—H15 | 119.7 |
C1—C2—C3 | 120.47 (11) | C17—C16—C15 | 119.75 (14) |
C1—C2—H2 | 119.8 | C17—C16—H16 | 120.1 |
C3—C2—H2 | 119.8 | C15—C16—H16 | 120.1 |
C4—C3—C2 | 120.75 (11) | C16—C17—C18 | 120.32 (15) |
C4—C3—H3 | 119.6 | C16—C17—H17 | 119.8 |
C2—C3—H3 | 119.6 | C18—C17—H17 | 119.8 |
C3—C4—C10 | 120.63 (11) | C17—C18—C13 | 119.55 (14) |
C3—C4—C19 | 118.30 (11) | C17—C18—H18 | 120.2 |
C10—C4—C19 | 120.79 (11) | C13—C18—H18 | 120.2 |
C6—C5—C10 | 120.94 (12) | O2—C19—N2 | 122.19 (12) |
C6—C5—H5 | 119.5 | O2—C19—C4 | 120.00 (11) |
C10—C5—H5 | 119.5 | N2—C19—C4 | 117.74 (11) |
C5—C6—C7 | 120.34 (12) | N2—C20—H20A | 109.5 |
C5—C6—H6 | 119.8 | N2—C20—H20B | 109.5 |
C7—C6—H6 | 119.8 | H20A—C20—H20B | 109.5 |
C8—C7—C6 | 120.41 (12) | N2—C20—H20C | 109.5 |
C8—C7—H7 | 119.8 | H20A—C20—H20C | 109.5 |
C6—C7—H7 | 119.8 | H20B—C20—H20C | 109.5 |
C7—C8—C9 | 121.13 (12) | C22—C21—C26 | 119.48 (14) |
C7—C8—H8 | 119.4 | C22—C21—N2 | 120.95 (11) |
C9—C8—H8 | 119.4 | C26—C21—N2 | 119.50 (14) |
C8—C9—C1 | 122.74 (11) | C23—C22—C21 | 120.40 (15) |
C8—C9—C10 | 118.54 (11) | C23—C22—H22 | 119.8 |
C1—C9—C10 | 118.72 (11) | C21—C22—H22 | 119.8 |
C4—C10—C5 | 122.54 (11) | C24—C23—C22 | 120.59 (18) |
C4—C10—C9 | 118.83 (11) | C24—C23—H23 | 119.7 |
C5—C10—C9 | 118.63 (11) | C22—C23—H23 | 119.7 |
O1—C11—N1 | 122.12 (11) | C25—C24—C23 | 119.46 (17) |
O1—C11—C1 | 120.70 (11) | C25—C24—H24 | 120.3 |
N1—C11—C1 | 117.18 (10) | C23—C24—H24 | 120.3 |
N1—C12—H12A | 109.5 | C24—C25—C26 | 121.53 (16) |
N1—C12—H12B | 109.5 | C24—C25—H25 | 119.2 |
H12A—C12—H12B | 109.5 | C26—C25—H25 | 119.2 |
N1—C12—H12C | 109.5 | C21—C26—C25 | 118.52 (19) |
H12A—C12—H12C | 109.5 | C21—C26—H26 | 120.7 |
H12B—C12—H12C | 109.5 | C25—C26—H26 | 120.7 |
C9—C1—C2—C3 | 0.62 (18) | C11—N1—C13—C14 | −70.76 (17) |
C11—C1—C2—C3 | −176.18 (11) | C12—N1—C13—C14 | 117.40 (13) |
C1—C2—C3—C4 | −0.63 (19) | C11—N1—C13—C18 | 111.51 (14) |
C2—C3—C4—C10 | −0.15 (18) | C12—N1—C13—C18 | −60.33 (16) |
C2—C3—C4—C19 | 173.82 (11) | C18—C13—C14—C15 | −0.5 (2) |
C10—C5—C6—C7 | 0.19 (19) | N1—C13—C14—C15 | −178.25 (12) |
C5—C6—C7—C8 | −0.6 (2) | C13—C14—C15—C16 | 0.4 (2) |
C6—C7—C8—C9 | 0.2 (2) | C14—C15—C16—C17 | −0.1 (2) |
C7—C8—C9—C1 | −178.76 (12) | C15—C16—C17—C18 | −0.1 (2) |
C7—C8—C9—C10 | 0.67 (18) | C16—C17—C18—C13 | 0.0 (2) |
C2—C1—C9—C8 | 179.58 (11) | C14—C13—C18—C17 | 0.3 (2) |
C11—C1—C9—C8 | −3.59 (18) | N1—C13—C18—C17 | 178.08 (13) |
C2—C1—C9—C10 | 0.16 (17) | C21—N2—C19—O2 | −175.71 (12) |
C11—C1—C9—C10 | 176.98 (10) | C20—N2—C19—O2 | 7.03 (19) |
C3—C4—C10—C5 | −178.34 (11) | C21—N2—C19—C4 | 7.42 (18) |
C19—C4—C10—C5 | 7.84 (17) | C20—N2—C19—C4 | −169.84 (12) |
C3—C4—C10—C9 | 0.91 (17) | C3—C4—C19—O2 | −109.93 (14) |
C19—C4—C10—C9 | −172.90 (10) | C10—C4—C19—O2 | 64.03 (16) |
C6—C5—C10—C4 | 179.92 (12) | C3—C4—C19—N2 | 67.01 (15) |
C6—C5—C10—C9 | 0.66 (18) | C10—C4—C19—N2 | −119.03 (13) |
C8—C9—C10—C4 | 179.64 (10) | C19—N2—C21—C22 | 53.51 (18) |
C1—C9—C10—C4 | −0.91 (16) | C20—N2—C21—C22 | −129.20 (14) |
C8—C9—C10—C5 | −1.07 (17) | C19—N2—C21—C26 | −129.46 (14) |
C1—C9—C10—C5 | 178.38 (10) | C20—N2—C21—C26 | 47.84 (17) |
C13—N1—C11—O1 | −173.60 (12) | C26—C21—C22—C23 | 1.5 (2) |
C12—N1—C11—O1 | −1.91 (18) | N2—C21—C22—C23 | 178.52 (12) |
C13—N1—C11—C1 | 6.50 (17) | C21—C22—C23—C24 | −0.7 (2) |
C12—N1—C11—C1 | 178.19 (11) | C22—C23—C24—C25 | −0.5 (3) |
C2—C1—C11—O1 | 115.16 (14) | C23—C24—C25—C26 | 0.8 (3) |
C9—C1—C11—O1 | −61.68 (16) | C22—C21—C26—C25 | −1.2 (2) |
C2—C1—C11—N1 | −64.93 (16) | N2—C21—C26—C25 | −178.23 (13) |
C9—C1—C11—N1 | 118.22 (12) | C24—C25—C26—C21 | 0.0 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···Cg1i | 0.95 | 2.82 | 3.614 (1) | 142 |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C26H22N2O2 |
Mr | 394.46 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 153 |
a, b, c (Å) | 8.9970 (6), 9.3627 (5), 13.5538 (7) |
α, β, γ (°) | 105.329 (1), 92.391 (2), 111.656 (2) |
V (Å3) | 1010.95 (10) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.55 × 0.33 × 0.21 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9974, 4593, 3695 |
Rint | 0.017 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.039, 0.136, 1.00 |
No. of reflections | 4593 |
No. of parameters | 274 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.35, −0.26 |
Computer programs: RAPID-AUTO (Rigaku/MSC, 2004), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), XP in SHELXTL (Bruker, 1997).
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···Cg1i | 0.95 | 2.82 | 3.614 (1) | 142 |
Symmetry code: (i) −x+1, −y+1, −z+1. |
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1,4-Naphthalenedicarboxylic acid derivatives are a class of intermediates important for applications as monomers in the preparation of polymers (Fukuzumi et al., 1994; Tsukada et al., 1994). Previously, we have reported the crystal structures of N,N'-bis(4-nitrophenyl)naphthalene-1,4-dicarboxamide dimethylsulfoxide disolvate (Jing, Qin, Gu, Zhang & Mao, 2006) and N,N'-bis(2-methoxyphenyl)naphthalene-1,4-dicarboxamide (Jing, Qin, Gu, Zhang & Lei, 2006). We now report the crystal structure of the title compound, (I).
The bond lengths and angles in (I) are normal. The naphthalene ring system is planar, with a maximum deviation of 0.017 (1) Å for atom C2. As a result of steric effects, two amide groups (O1/N1/C1/C11 and O2/N2/C4/C19) are twisted away from the naphthalene mean plane by 63.94 (3) and 66.07 (3)°, respectively (Fig. 1). The dihedral angle between the O1/N1/C1/C11 and C13—C18 planes is 65.80 (5)°, and that between the O2/N2/C4/C19 and C21—C26 planes is 56.36 (6)°. The crystal packing is stabilized by intermolecular C—H···π interactions involving the C21—C26 phenyl ring (centroid Cg1; Table 1).