Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801004081/cf6054sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801004081/cf6054Isup2.hkl |
CCDC reference: 162814
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.007 Å
- R factor = 0.071
- wR factor = 0.303
- Data-to-parameter ratio = 18.6
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level C:
RFACR_01 Alert C The value of the weighted R factor is > 0.25 Weighted R factor given 0.303 PLAT_371 Alert C Long C(sp2)-C(sp1) Bond C(1) - C(2) = 1.44 Ang.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
2 Alert Level C = Please check
The title compound (CP10OB) was prepared by esterification of 4-cyanophenol with 4-n-decanyloxybenzoyl chloride. Single crystals of CP10OB were obtained by recrystallization from ethyl acetate.
All H atoms were located at ideal positions and constrained with Uiso held fixed to 1.2Ueq of the parent atoms.
Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: MolEN (Fair, 1990); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: Xtal_GX (Hall & du Boulay, 1995); software used to prepare material for publication: SHELXL97.
Fig. 1. The molecular structure of CP10OB showing 50% probability displacement ellipsoids. | |
Fig. 2. Packing diagram viewed down the a axis. H atoms have been omitted for clarity. |
C24H29NO3 | Z = 2 |
Mr = 379.48 | F(000) = 408 |
Triclinic, P1 | Dx = 1.162 Mg m−3 |
a = 10.9982 (17) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 14.850 (2) Å | Cell parameters from 25 reflections |
c = 6.7625 (6) Å | θ = 8.8–18.1° |
α = 96.864 (9)° | µ = 0.08 mm−1 |
β = 93.694 (9)° | T = 296 K |
γ = 81.945 (12)° | Prism, colorless |
V = 1084.5 (2) Å3 | 0.47 × 0.37 × 0.34 mm |
Enraf-Nonius CAD-4 diffractometer | 1517 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.079 |
Graphite monochromator | θmax = 27.0°, θmin = 3.6° |
ω–2θ scans | h = −14→14 |
Absorption correction: ψ scan (North et al., 1968) | k = −18→18 |
Tmin = 0.926, Tmax = 1.000 | l = 0→8 |
5095 measured reflections | 3 standard reflections every 120 min |
4695 independent reflections | intensity decay: 0.7% |
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)] = 0.071 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.303 | H-atom parameters constrained |
S = 0.92 | w = 1/[σ2(Fo2) + (0.1516P)2] where P = (Fo2 + 2Fc2)/3 |
4695 reflections | (Δ/σ)max < 0.001 |
253 parameters | Δρmax = 0.35 e Å−3 |
0 restraints | Δρmin = −0.43 e Å−3 |
C24H29NO3 | γ = 81.945 (12)° |
Mr = 379.48 | V = 1084.5 (2) Å3 |
Triclinic, P1 | Z = 2 |
a = 10.9982 (17) Å | Mo Kα radiation |
b = 14.850 (2) Å | µ = 0.08 mm−1 |
c = 6.7625 (6) Å | T = 296 K |
α = 96.864 (9)° | 0.47 × 0.37 × 0.34 mm |
β = 93.694 (9)° |
Enraf-Nonius CAD-4 diffractometer | 1517 reflections with I > 2σ(I) |
Absorption correction: ψ scan (North et al., 1968) | Rint = 0.079 |
Tmin = 0.926, Tmax = 1.000 | 3 standard reflections every 120 min |
5095 measured reflections | intensity decay: 0.7% |
4695 independent reflections |
R[F2 > 2σ(F2)] = 0.071 | 0 restraints |
wR(F2) = 0.303 | H-atom parameters constrained |
S = 0.92 | Δρmax = 0.35 e Å−3 |
4695 reflections | Δρmin = −0.43 e Å−3 |
253 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 | 1.4310 (5) | 0.4653 (4) | −0.7411 (8) | 0.0903 (18) | |
O1 | 0.8982 (4) | 0.4366 (3) | −0.1312 (6) | 0.0811 (14) | |
O2 | 1.0699 (3) | 0.3369 (2) | −0.0946 (5) | 0.0557 (10) | |
O3 | 0.7841 (3) | 0.2094 (2) | 0.5610 (5) | 0.0659 (11) | |
C1 | 1.3670 (5) | 0.4469 (4) | −0.6322 (8) | 0.0595 (15) | |
C2 | 1.2875 (4) | 0.4210 (3) | −0.4936 (7) | 0.0452 (12) | |
C3 | 1.1648 (5) | 0.4156 (3) | −0.5480 (8) | 0.0541 (14) | |
H3 | 1.1339 | 0.4290 | −0.6740 | 0.065* | |
C4 | 1.0883 (4) | 0.3904 (3) | −0.4166 (8) | 0.0530 (14) | |
H4 | 1.0059 | 0.3868 | −0.4525 | 0.064* | |
C5 | 1.1363 (4) | 0.3706 (3) | −0.2308 (7) | 0.0449 (12) | |
C6 | 1.2577 (4) | 0.3759 (3) | −0.1754 (8) | 0.0541 (14) | |
H6 | 1.2883 | 0.3619 | −0.0497 | 0.065* | |
C7 | 1.3337 (5) | 0.4016 (3) | −0.3049 (8) | 0.0547 (14) | |
H7 | 1.4156 | 0.4061 | −0.2668 | 0.066* | |
C8 | 0.9525 (5) | 0.3743 (3) | −0.0512 (7) | 0.0497 (13) | |
C9 | 0.9067 (4) | 0.3282 (3) | 0.1030 (7) | 0.0435 (12) | |
C10 | 0.7958 (5) | 0.3650 (3) | 0.1836 (8) | 0.0538 (14) | |
H10 | 0.7506 | 0.4158 | 0.1335 | 0.065* | |
C11 | 0.7508 (4) | 0.3277 (3) | 0.3376 (7) | 0.0516 (13) | |
H11 | 0.6765 | 0.3535 | 0.3917 | 0.062* | |
C12 | 0.8174 (4) | 0.2519 (3) | 0.4094 (7) | 0.0494 (13) | |
C13 | 0.9266 (5) | 0.2127 (3) | 0.3245 (8) | 0.0586 (15) | |
H13 | 0.9696 | 0.1598 | 0.3690 | 0.070* | |
C14 | 0.9713 (4) | 0.2517 (3) | 0.1752 (7) | 0.0498 (13) | |
H14 | 1.0460 | 0.2262 | 0.1222 | 0.060* | |
C15 | 0.6759 (4) | 0.2465 (3) | 0.6631 (7) | 0.0540 (14) | |
H15A | 0.6045 | 0.2484 | 0.5711 | 0.065* | |
H15B | 0.6826 | 0.3082 | 0.7244 | 0.065* | |
C16 | 0.6644 (5) | 0.1847 (3) | 0.8201 (8) | 0.0560 (14) | |
H16A | 0.7352 | 0.1855 | 0.9133 | 0.067* | |
H16B | 0.6644 | 0.1225 | 0.7571 | 0.067* | |
C17 | 0.5486 (4) | 0.2131 (4) | 0.9333 (7) | 0.0543 (14) | |
H17A | 0.4781 | 0.2136 | 0.8395 | 0.065* | |
H17B | 0.5496 | 0.2750 | 0.9980 | 0.065* | |
C18 | 0.5339 (5) | 0.1506 (3) | 1.0900 (8) | 0.0561 (14) | |
H18A | 0.5356 | 0.0885 | 1.0252 | 0.067* | |
H18B | 0.6038 | 0.1513 | 1.1849 | 0.067* | |
C19 | 0.4179 (5) | 0.1752 (4) | 1.2028 (8) | 0.0601 (15) | |
H19A | 0.3479 | 0.1765 | 1.1078 | 0.072* | |
H19B | 0.4174 | 0.2364 | 1.2717 | 0.072* | |
C20 | 0.4023 (5) | 0.1106 (4) | 1.3533 (8) | 0.0620 (15) | |
H20A | 0.4054 | 0.0492 | 1.2846 | 0.074* | |
H20B | 0.4714 | 0.1107 | 1.4500 | 0.074* | |
C21 | 0.2865 (5) | 0.1322 (4) | 1.4627 (9) | 0.0694 (16) | |
H21A | 0.2173 | 0.1308 | 1.3665 | 0.083* | |
H21B | 0.2825 | 0.1940 | 1.5294 | 0.083* | |
C22 | 0.2732 (5) | 0.0682 (4) | 1.6161 (9) | 0.0740 (18) | |
H22A | 0.2759 | 0.0065 | 1.5488 | 0.089* | |
H22B | 0.3434 | 0.0687 | 1.7105 | 0.089* | |
C23 | 0.1588 (6) | 0.0901 (5) | 1.7294 (11) | 0.104 (3) | |
H23A | 0.1547 | 0.1524 | 1.7932 | 0.125* | |
H23B | 0.0886 | 0.0875 | 1.6355 | 0.125* | |
C24 | 0.1481 (8) | 0.0293 (5) | 1.8831 (13) | 0.128 (3) | |
H24A | 0.0719 | 0.0480 | 1.9473 | 0.192* | |
H24B | 0.2154 | 0.0330 | 1.9803 | 0.192* | |
H24C | 0.1503 | −0.0326 | 1.8217 | 0.192* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.083 (4) | 0.139 (5) | 0.062 (4) | −0.050 (3) | 0.012 (3) | 0.021 (3) |
O1 | 0.076 (3) | 0.094 (3) | 0.078 (3) | 0.017 (2) | 0.025 (2) | 0.052 (3) |
O2 | 0.054 (2) | 0.065 (2) | 0.053 (2) | −0.0008 (17) | 0.0133 (18) | 0.0301 (18) |
O3 | 0.066 (2) | 0.075 (3) | 0.064 (3) | −0.0018 (19) | 0.019 (2) | 0.038 (2) |
C1 | 0.062 (4) | 0.076 (4) | 0.045 (3) | −0.025 (3) | 0.002 (3) | 0.009 (3) |
C2 | 0.050 (3) | 0.049 (3) | 0.040 (3) | −0.012 (2) | 0.010 (2) | 0.004 (2) |
C3 | 0.057 (3) | 0.067 (3) | 0.040 (3) | −0.010 (3) | −0.001 (3) | 0.016 (3) |
C4 | 0.045 (3) | 0.071 (4) | 0.047 (3) | −0.014 (3) | −0.001 (3) | 0.016 (3) |
C5 | 0.052 (3) | 0.048 (3) | 0.039 (3) | −0.004 (2) | 0.011 (2) | 0.016 (2) |
C6 | 0.049 (3) | 0.072 (4) | 0.045 (3) | −0.008 (3) | −0.002 (3) | 0.024 (3) |
C7 | 0.045 (3) | 0.066 (3) | 0.055 (4) | −0.011 (2) | 0.001 (3) | 0.012 (3) |
C8 | 0.056 (3) | 0.052 (3) | 0.043 (3) | −0.007 (3) | 0.002 (3) | 0.012 (3) |
C9 | 0.048 (3) | 0.045 (3) | 0.041 (3) | −0.009 (2) | 0.003 (2) | 0.014 (2) |
C10 | 0.054 (3) | 0.057 (3) | 0.052 (3) | −0.002 (2) | 0.006 (3) | 0.019 (3) |
C11 | 0.053 (3) | 0.055 (3) | 0.048 (3) | −0.003 (2) | 0.013 (3) | 0.009 (3) |
C12 | 0.052 (3) | 0.054 (3) | 0.048 (3) | −0.014 (2) | 0.008 (3) | 0.016 (3) |
C13 | 0.054 (3) | 0.058 (3) | 0.067 (4) | 0.001 (3) | 0.012 (3) | 0.027 (3) |
C14 | 0.049 (3) | 0.056 (3) | 0.047 (3) | −0.003 (2) | 0.011 (2) | 0.017 (3) |
C15 | 0.055 (3) | 0.066 (3) | 0.047 (3) | −0.016 (3) | 0.008 (3) | 0.016 (3) |
C16 | 0.065 (3) | 0.063 (3) | 0.047 (3) | −0.017 (3) | 0.008 (3) | 0.018 (3) |
C17 | 0.058 (3) | 0.070 (3) | 0.040 (3) | −0.017 (3) | −0.001 (3) | 0.020 (3) |
C18 | 0.058 (3) | 0.062 (3) | 0.053 (3) | −0.009 (2) | 0.012 (3) | 0.018 (3) |
C19 | 0.063 (3) | 0.069 (4) | 0.052 (3) | −0.009 (3) | 0.010 (3) | 0.018 (3) |
C20 | 0.062 (4) | 0.064 (4) | 0.064 (4) | −0.007 (3) | 0.017 (3) | 0.016 (3) |
C21 | 0.066 (4) | 0.086 (4) | 0.059 (4) | 0.001 (3) | 0.021 (3) | 0.024 (3) |
C22 | 0.080 (4) | 0.081 (4) | 0.068 (4) | −0.014 (3) | 0.026 (3) | 0.018 (3) |
C23 | 0.097 (5) | 0.131 (6) | 0.094 (5) | 0.001 (4) | 0.040 (4) | 0.053 (5) |
C24 | 0.158 (8) | 0.113 (6) | 0.127 (7) | −0.031 (5) | 0.063 (6) | 0.025 (5) |
N1—C1 | 1.132 (6) | C15—H15A | 0.970 |
O1—C8 | 1.195 (6) | C15—H15B | 0.970 |
O2—C8 | 1.367 (6) | C16—C17 | 1.511 (6) |
O2—C5 | 1.390 (5) | C16—H16A | 0.970 |
O3—C12 | 1.360 (5) | C16—H16B | 0.970 |
O3—C15 | 1.424 (5) | C17—C18 | 1.520 (6) |
C1—C2 | 1.441 (7) | C17—H17A | 0.970 |
C2—C3 | 1.386 (6) | C17—H17B | 0.970 |
C2—C7 | 1.391 (7) | C18—C19 | 1.507 (6) |
C3—C4 | 1.379 (6) | C18—H18A | 0.970 |
C3—H3 | 0.930 | C18—H18B | 0.970 |
C4—C5 | 1.379 (6) | C19—C20 | 1.513 (6) |
C4—H4 | 0.930 | C19—H19A | 0.970 |
C5—C6 | 1.373 (6) | C19—H19B | 0.970 |
C6—C7 | 1.369 (6) | C20—C21 | 1.490 (7) |
C6—H6 | 0.930 | C20—H20A | 0.970 |
C7—H7 | 0.930 | C20—H20B | 0.970 |
C8—C9 | 1.465 (6) | C21—C22 | 1.515 (7) |
C9—C14 | 1.377 (6) | C21—H21A | 0.970 |
C9—C10 | 1.382 (6) | C21—H21B | 0.970 |
C10—C11 | 1.385 (6) | C22—C23 | 1.492 (8) |
C10—H10 | 0.930 | C22—H22A | 0.970 |
C11—C12 | 1.376 (6) | C22—H22B | 0.970 |
C11—H11 | 0.930 | C23—C24 | 1.475 (8) |
C12—C13 | 1.387 (7) | C23—H23A | 0.970 |
C13—C14 | 1.371 (6) | C23—H23B | 0.970 |
C13—H13 | 0.930 | C24—H24A | 0.960 |
C14—H14 | 0.930 | C24—H24B | 0.960 |
C15—C16 | 1.507 (6) | C24—H24C | 0.960 |
C8—O2—C5 | 122.3 (4) | C15—C16—H16B | 109.1 |
C12—O3—C15 | 119.5 (4) | C17—C16—H16B | 109.1 |
N1—C1—C2 | 178.4 (7) | H16A—C16—H16B | 107.9 |
C3—C2—C7 | 119.9 (4) | C16—C17—C18 | 113.3 (4) |
C3—C2—C1 | 120.1 (5) | C16—C17—H17A | 108.9 |
C7—C2—C1 | 120.0 (5) | C18—C17—H17A | 108.9 |
C4—C3—C2 | 120.4 (5) | C16—C17—H17B | 108.9 |
C4—C3—H3 | 119.8 | C18—C17—H17B | 108.9 |
C2—C3—H3 | 119.8 | H17A—C17—H17B | 107.7 |
C5—C4—C3 | 118.7 (5) | C19—C18—C17 | 114.9 (4) |
C5—C4—H4 | 120.6 | C19—C18—H18A | 108.5 |
C3—C4—H4 | 120.6 | C17—C18—H18A | 108.5 |
C6—C5—C4 | 121.3 (4) | C19—C18—H18B | 108.5 |
C6—C5—O2 | 115.4 (4) | C17—C18—H18B | 108.5 |
C4—C5—O2 | 123.1 (4) | H18A—C18—H18B | 107.5 |
C7—C6—C5 | 120.2 (5) | C18—C19—C20 | 114.4 (4) |
C7—C6—H6 | 119.9 | C18—C19—H19A | 108.7 |
C5—C6—H6 | 119.9 | C20—C19—H19A | 108.7 |
C6—C7—C2 | 119.5 (5) | C18—C19—H19B | 108.7 |
C6—C7—H7 | 120.2 | C20—C19—H19B | 108.7 |
C2—C7—H7 | 120.2 | H19A—C19—H19B | 107.6 |
O1—C8—O2 | 122.7 (4) | C21—C20—C19 | 115.4 (4) |
O1—C8—C9 | 126.5 (5) | C21—C20—H20A | 108.4 |
O2—C8—C9 | 110.8 (4) | C19—C20—H20A | 108.4 |
C14—C9—C10 | 118.8 (4) | C21—C20—H20B | 108.4 |
C14—C9—C8 | 122.7 (4) | C19—C20—H20B | 108.4 |
C10—C9—C8 | 118.4 (4) | H20A—C20—H20B | 107.5 |
C9—C10—C11 | 121.2 (5) | C20—C21—C22 | 114.8 (5) |
C9—C10—H10 | 119.4 | C20—C21—H21A | 108.6 |
C11—C10—H10 | 119.4 | C22—C21—H21A | 108.6 |
C12—C11—C10 | 119.1 (5) | C20—C21—H21B | 108.6 |
C12—C11—H11 | 120.5 | C22—C21—H21B | 108.6 |
C10—C11—H11 | 120.5 | H21A—C21—H21B | 107.5 |
O3—C12—C11 | 124.9 (5) | C23—C22—C21 | 115.4 (5) |
O3—C12—C13 | 115.2 (5) | C23—C22—H22A | 108.4 |
C11—C12—C13 | 120.0 (4) | C21—C22—H22A | 108.4 |
C14—C13—C12 | 120.2 (5) | C23—C22—H22B | 108.4 |
C14—C13—H13 | 119.9 | C21—C22—H22B | 108.4 |
C12—C13—H13 | 119.9 | H22A—C22—H22B | 107.5 |
C13—C14—C9 | 120.6 (5) | C24—C23—C22 | 115.2 (6) |
C13—C14—H14 | 119.7 | C24—C23—H23A | 108.5 |
C9—C14—H14 | 119.7 | C22—C23—H23A | 108.5 |
O3—C15—C16 | 106.6 (4) | C24—C23—H23B | 108.5 |
O3—C15—H15A | 110.4 | C22—C23—H23B | 108.5 |
C16—C15—H15A | 110.4 | H23A—C23—H23B | 107.5 |
O3—C15—H15B | 110.4 | C23—C24—H24A | 109.5 |
C16—C15—H15B | 110.4 | C23—C24—H24B | 109.5 |
H15A—C15—H15B | 108.6 | H24A—C24—H24B | 109.5 |
C15—C16—C17 | 112.4 (4) | C23—C24—H24C | 109.5 |
C15—C16—H16A | 109.1 | H24A—C24—H24C | 109.5 |
C17—C16—H16A | 109.1 | H24B—C24—H24C | 109.5 |
C7—C2—C3—C4 | −0.5 (7) | C9—C10—C11—C12 | −0.8 (7) |
C1—C2—C3—C4 | 179.7 (5) | C15—O3—C12—C11 | −3.2 (7) |
C2—C3—C4—C5 | −0.1 (7) | C15—O3—C12—C13 | 177.6 (5) |
C3—C4—C5—C6 | 0.2 (8) | C10—C11—C12—O3 | 179.3 (5) |
C3—C4—C5—O2 | −174.1 (4) | C10—C11—C12—C13 | −1.5 (8) |
C8—O2—C5—C6 | 138.4 (5) | O3—C12—C13—C14 | −177.7 (5) |
C8—O2—C5—C4 | −47.0 (7) | C11—C12—C13—C14 | 3.0 (8) |
C4—C5—C6—C7 | 0.4 (8) | C12—C13—C14—C9 | −2.2 (8) |
O2—C5—C6—C7 | 175.1 (4) | C10—C9—C14—C13 | −0.1 (7) |
C5—C6—C7—C2 | −1.0 (8) | C8—C9—C14—C13 | 177.8 (5) |
C3—C2—C7—C6 | 1.0 (7) | C12—O3—C15—C16 | 179.9 (4) |
C1—C2—C7—C6 | −179.1 (5) | O3—C15—C16—C17 | −176.8 (4) |
C5—O2—C8—O1 | 2.1 (8) | C15—C16—C17—C18 | 178.9 (4) |
C5—O2—C8—C9 | −177.5 (4) | C16—C17—C18—C19 | −178.6 (5) |
O1—C8—C9—C14 | 174.2 (5) | C17—C18—C19—C20 | 178.0 (5) |
O2—C8—C9—C14 | −6.2 (7) | C18—C19—C20—C21 | −178.4 (5) |
O1—C8—C9—C10 | −8.0 (8) | C19—C20—C21—C22 | −178.8 (5) |
O2—C8—C9—C10 | 171.6 (4) | C20—C21—C22—C23 | 178.9 (6) |
C14—C9—C10—C11 | 1.5 (7) | C21—C22—C23—C24 | −178.1 (6) |
C8—C9—C10—C11 | −176.4 (5) |
Experimental details
Crystal data | |
Chemical formula | C24H29NO3 |
Mr | 379.48 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 296 |
a, b, c (Å) | 10.9982 (17), 14.850 (2), 6.7625 (6) |
α, β, γ (°) | 96.864 (9), 93.694 (9), 81.945 (12) |
V (Å3) | 1084.5 (2) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.47 × 0.37 × 0.34 |
Data collection | |
Diffractometer | Enraf-Nonius CAD-4 diffractometer |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.926, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5095, 4695, 1517 |
Rint | 0.079 |
(sin θ/λ)max (Å−1) | 0.638 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.071, 0.303, 0.92 |
No. of reflections | 4695 |
No. of parameters | 253 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.35, −0.43 |
Computer programs: CAD-4 Software (Enraf-Nonius, 1989), CAD-4 Software, MolEN (Fair, 1990), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 1997), Xtal_GX (Hall & du Boulay, 1995), SHELXL97.
N1—C1 | 1.132 (6) | O3—C12 | 1.360 (5) |
O1—C8 | 1.195 (6) | C1—C2 | 1.441 (7) |
O2—C8 | 1.367 (6) | C8—C9 | 1.465 (6) |
O2—C5 | 1.390 (5) | ||
N1—C1—C2 | 178.4 (7) | O2—C8—C9 | 110.8 (4) |
C8—O2—C5—C4 | −47.0 (7) | O2—C8—C9—C10 | 171.6 (4) |
C5—O2—C8—O1 | 2.1 (8) | C12—O3—C15—C16 | 179.9 (4) |
C5—O2—C8—C9 | −177.5 (4) |
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Mesomorphic sequences of 4-cyanophenyl 4-n-alkoxybenzoates (CPnOB) are dependent on the length of the alkoxy chains, i.e. crystals–nematic–isotropic for n = 5–8, crystals–smectic A–nematic–isotropic for n = 9–11, and crystals–smectic A–isotropic for n = 12 (Vill, 2000). The crystal structures of CPnOB with some alkyl chains (n = 4, 5, 6, 7, 8, 12) have been reported (Baumeister et al., 1981; Ibrahim et al., 1995; Iki & Hori, 1995; Kubo & Mori, 2001). We now report the structures of 4-cyanophenyl 4-n-decanyloxybenzoate (CP10OB), to elucidate the relationships between mesomorphic properties and molecular packings of CPnOB in the crystal lattice.
The intersection angle between the least-squares planes A (defined by C2–C7) and B (defined by C9–C14) of CP10OB is 49.6 (2)°, which is similar to those [49.2 and 50.5 (1)°] of CP8OB (Iki & Hori, 1995) and CP12OB (Kubo & Mori, 2001), while that between the least-squares planes B and C (defined by O1/O2/C8) is 8.3 (3)°, which is similar to those (8.3 and 7.9°) of CP8OB and CP12OB. The paraffin chains have all-trans conformations and the molecular length of the compound is 25.323 (9) Å for the N1—C24 distance.
Intermolecular close contact between CN groups of a pair of antiparallel molecules is observed in the crystal lattice. The distance for C1—N1i [symmetry code: (i) 1 - x, 1 - y, -1 - z] is 3.50 (7) Å, which is similar to those (3.486 and 3.514 Å) of CP8OB (Iki & Hori, 1995) and CP12OB (Kubo & Mori, 2001), and shorter than those (3.829 and 3.602 Å) of CP4OB (Ibrahim et al., 1995) and CP6OB (Iki & Hori, 1995). Carbonyloxy groups of another pair of antiparallel molecules are also closely arranged. The distances for O1—O1ii [symmetry code: (ii) 2 - x, 1 - y, -z], O1—O2ii and O1—C8ii are 3.403 (6), 3.578 (5) and 3.508 (7) Å, respectively. In addition, close contacts between a CN and a carbonyloxy group of the other pair of molecules are observed; the distances for C1—O1iii [symmetry code: (iii) 2 - x, 1 - y, -1 - z] and N1—O1iii are 3.565 (7) and 3.794 (7) Å, respectively.
The crystal of CP10OB has a distinct layer structure through infinite networks of the CN···CN interaction, which is similar to those of CP8OB and CP12OB. In conclusion, correlations between crystal structure and mesomorphic properties of CPnOB with different smectic phases have not been found.