organic compounds
6-Cyanonaphthalen-2-yl 4-hexylbenzoate
aUniversity Malaysia Pahang, Faculty of Industrial Sciences and Technology, 26300 Gambang, Kuantan, Pahang, Malaysia, bRaman Research Institute, C.V. Raman Avenue, Sadashivanagar, Bangalore 560080, India, cSchool of Chemistry Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and dX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
*Correspondence e-mail: lutfor73@gmail.com
In the title compound, C24H23NO2, a whole molecule is disordered over two sets of sites with occupancies in a ratio of 0.692 (6):0.308 (6). In the major disorder component, the naphthalene ring system forms a dihedral angle of 68.6 (5)° with the benzene ring. The corresponding angle in the minor component is 81.6 (10)°. In the crystal, molecules are linked into chains propagating along the b-axis direction via weak C—H⋯O hydrogen bonds. The crystal packing is further consolidated by weak C—H⋯π interactions.
CCDC reference: 998819
Related literature
For features of electro-optical display devices, see: Cox & Clecak (1976); Reddy & Tschierske (2006); Hanasaki et al. (2011) For applications of cyano groups in displays, see: Coates & Gray (1976); Klingbiel et al. (1974); Takezoe & Takanishi (2006). For related structures, see: Kuzmina et al. (2010); Blake et al. (1995); Li (2006). For standard bond-length data, see: Allen et al. (1987).
Experimental
Crystal data
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Data collection: APEX2 (Bruker, 2009); cell SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).
Supporting information
CCDC reference: 998819
10.1107/S160053681400909X/lh5699sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S160053681400909X/lh5699Isup2.hkl
Supporting information file. DOI: 10.1107/S160053681400909X/lh5699Isup3.cml
A mixture of 4-hexylbenzoic acid (1.0 mmol), 2-cyano-6-hydroxy-naphthalene (1.0 mmol), dicyclohexylcarbodiimide (1.2 mmol) and catalytic quantity of N,N-dimethylaminopyridine in 5 ml of dry dichloromethane was stirred at room temperature for 1 h. Progress of the reaction was monitored by TLC (ethyl acetate: pet ether 2:8). After completion of the reaction, the reaction mass was diluted with water and extracted into dichloromethane (25 ml). The organic layer was washed with diluted acetic acid and water. The organic layer was dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. The crude product was purified by δ = 8.11–6.98 (m, 10H, Ar—H), 2.54 (t, J = 1.37 Hz, 2H, Ar—CH2–), 1.47–1.44 (m, 8H, alkyl-CH2–), 0.91 (m, 3H, alkyl-CH3) p.p.m.; Elemental analysis calcd for C24H23NO2 (%): C 80.64, H 6.49, N 3.92; found. C 80.69, H 6.54, N 4.07.
by using ethyl acetate: petroleum ether (2:8) as and the product was recrystallization from chloroform. Yield = 70% as colourless block crystals. IR(KBr): v = 2920, 2856, 2224, 1724, 1454, 1066, 902 cm-1; 1H NMR (400 MHz, CDCl3):The title compound is disordered over two positions with a refined site-occupancy ratio of 0.692 (6): 0.308 (6) and the minor disordered component was refined isotropically. All H atoms were positioned geometrically [C—H = 0.95–0.99 Å] and refined using a riding model with Uiso(H) = 1.2 or 1.5 Ueq(C). A rotating group model was applied to the methyl groups. The restraints of same geometries were applied to all disordered components. Identical anisotropic displacement and distance restraint were used in the final
Similarity were applied to the disordered atoms. DFIX restraints of 1.50 (1) Å were used for the long-disordered alkyl chains such as C19B—C20B, C21B—C22B, C22B—C23B, C23B—C24B and C23A—C24A distances. Same Uij parameters restraints were used for C22A/C23A and C22B/C23B atom pairs. One outlier (1 1 10) was omitted from the reflection data.Data collection: APEX2 (Bruker, 2009); cell
SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).Fig. 1. : The molecular structure of the title compound showing 30% probability displacement ellipsoids for the major component of disorder. Open bonds show the minor disordered component. | |
Fig. 2. : The crystal packing of the title compound. Dashed lines represent the intermolecular hydrogen bonds. Only major disordered component is shown. |
C24H23NO2 | F(000) = 1520 |
Mr = 357.43 | Dx = 1.176 Mg m−3 |
Monoclinic, C2/c | Cu Kα radiation, λ = 1.54178 Å |
Hall symbol: -C 2yc | Cell parameters from 5436 reflections |
a = 14.4712 (2) Å | θ = 3.0–59.5° |
b = 9.5592 (2) Å | µ = 0.59 mm−1 |
c = 29.5386 (5) Å | T = 298 K |
β = 98.898 (1)° | Block, colourless |
V = 4036.99 (12) Å3 | 0.29 × 0.11 × 0.08 mm |
Z = 8 |
Bruker SMART APEXII CCD area-detector diffractometer | 3574 independent reflections |
Radiation source: fine-focus sealed tube | 2344 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.026 |
ϕ and ω scans | θmax = 67.5°, θmin = 3.0° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −17→17 |
Tmin = 0.848, Tmax = 0.954 | k = −11→10 |
15700 measured reflections | l = −35→34 |
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)] = 0.069 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.268 | H-atom parameters constrained |
S = 1.10 | w = 1/[σ2(Fo2) + (0.1621P)2 + 0.4013P] where P = (Fo2 + 2Fc2)/3 |
3574 reflections | (Δ/σ)max = 0.001 |
348 parameters | Δρmax = 0.25 e Å−3 |
73 restraints | Δρmin = −0.22 e Å−3 |
C24H23NO2 | V = 4036.99 (12) Å3 |
Mr = 357.43 | Z = 8 |
Monoclinic, C2/c | Cu Kα radiation |
a = 14.4712 (2) Å | µ = 0.59 mm−1 |
b = 9.5592 (2) Å | T = 298 K |
c = 29.5386 (5) Å | 0.29 × 0.11 × 0.08 mm |
β = 98.898 (1)° |
Bruker SMART APEXII CCD area-detector diffractometer | 3574 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | 2344 reflections with I > 2σ(I) |
Tmin = 0.848, Tmax = 0.954 | Rint = 0.026 |
15700 measured reflections |
R[F2 > 2σ(F2)] = 0.069 | 73 restraints |
wR(F2) = 0.268 | H-atom parameters constrained |
S = 1.10 | Δρmax = 0.25 e Å−3 |
3574 reflections | Δρmin = −0.22 e Å−3 |
348 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 | Occ. (<1) | |
N1A | 0.4778 (8) | 0.1930 (11) | 0.99962 (18) | 0.145 (3) | 0.692 (6) |
C1A | 0.4583 (9) | 0.1754 (13) | 0.9609 (2) | 0.161 (4) | 0.692 (6) |
C2A | 0.4351 (12) | 0.1379 (10) | 0.9130 (2) | 0.121 (5) | 0.692 (6) |
C3A | 0.4307 (11) | −0.0035 (9) | 0.8995 (3) | 0.125 (5) | 0.692 (6) |
H3AA | 0.4415 | −0.0758 | 0.9218 | 0.150* | 0.692 (6) |
C4A | 0.4110 (9) | −0.0350 (9) | 0.8543 (3) | 0.130 (4) | 0.692 (6) |
H4AA | 0.4045 | −0.1304 | 0.8453 | 0.156* | 0.692 (6) |
C5A | 0.3996 (15) | 0.0695 (7) | 0.8201 (2) | 0.095 (5) | 0.692 (6) |
C6A | 0.3754 (5) | 0.0381 (5) | 0.77329 (15) | 0.090 (2) | 0.692 (6) |
H6AA | 0.3707 | −0.0566 | 0.7635 | 0.108* | 0.692 (6) |
C7A | 0.3590 (10) | 0.1417 (10) | 0.7424 (2) | 0.113 (5) | 0.692 (6) |
C8A | 0.3659 (11) | 0.2835 (11) | 0.7551 (3) | 0.154 (5) | 0.692 (6) |
H8AA | 0.3557 | 0.3550 | 0.7325 | 0.185* | 0.692 (6) |
C9A | 0.3874 (10) | 0.3163 (8) | 0.8002 (3) | 0.146 (5) | 0.692 (6) |
H9AA | 0.3895 | 0.4117 | 0.8093 | 0.175* | 0.692 (6) |
C10A | 0.4066 (15) | 0.2110 (8) | 0.8340 (2) | 0.109 (4) | 0.692 (6) |
C11A | 0.4239 (8) | 0.2407 (9) | 0.8809 (3) | 0.137 (4) | 0.692 (6) |
H11A | 0.4280 | 0.3356 | 0.8906 | 0.164* | 0.692 (6) |
O1A | 0.3432 (3) | 0.1110 (9) | 0.69588 (13) | 0.116 (3) | 0.692 (6) |
O2A | 0.1939 (3) | 0.1789 (6) | 0.69048 (16) | 0.1168 (13) | 0.692 (6) |
C12A | 0.2548 (5) | 0.1298 (13) | 0.6719 (2) | 0.122 (4) | 0.692 (6) |
C13A | 0.2471 (4) | 0.0879 (13) | 0.62349 (17) | 0.099 (2) | 0.692 (6) |
C14A | 0.3195 (3) | 0.0298 (8) | 0.60548 (14) | 0.1111 (15) | 0.692 (6) |
H14A | 0.3777 | 0.0133 | 0.6245 | 0.133* | 0.692 (6) |
C15A | 0.3080 (3) | −0.0047 (8) | 0.55975 (13) | 0.1260 (17) | 0.692 (6) |
H15A | 0.3590 | −0.0449 | 0.5477 | 0.151* | 0.692 (6) |
C16A | 0.2256 (3) | 0.0168 (8) | 0.53108 (13) | 0.1217 (16) | 0.692 (6) |
C17A | 0.1539 (5) | 0.0786 (19) | 0.5497 (2) | 0.134 (4) | 0.692 (6) |
H17A | 0.0962 | 0.0977 | 0.5306 | 0.161* | 0.692 (6) |
C18A | 0.1643 (5) | 0.1128 (14) | 0.5950 (2) | 0.137 (4) | 0.692 (6) |
H18A | 0.1137 | 0.1544 | 0.6070 | 0.164* | 0.692 (6) |
C19A | 0.2169 (5) | −0.0254 (9) | 0.48135 (16) | 0.171 (3) | 0.692 (6) |
H19A | 0.2802 | −0.0236 | 0.4726 | 0.206* | 0.692 (6) |
H19B | 0.1948 | −0.1235 | 0.4787 | 0.206* | 0.692 (6) |
C20A | 0.1562 (6) | 0.0569 (8) | 0.44850 (17) | 0.198 (3) | 0.692 (6) |
H20A | 0.1738 | 0.1563 | 0.4536 | 0.237* | 0.692 (6) |
H20B | 0.0916 | 0.0465 | 0.4553 | 0.237* | 0.692 (6) |
C21A | 0.1545 (5) | 0.0258 (10) | 0.39913 (17) | 0.181 (3) | 0.692 (6) |
H21A | 0.1073 | 0.0879 | 0.3815 | 0.218* | 0.692 (6) |
H21B | 0.2161 | 0.0524 | 0.3912 | 0.218* | 0.692 (6) |
C22A | 0.1342 (9) | −0.1186 (11) | 0.3829 (2) | 0.250 (4) | 0.692 (6) |
H22A | 0.0863 | −0.1630 | 0.3987 | 0.300* | 0.692 (6) |
H22B | 0.1914 | −0.1770 | 0.3872 | 0.300* | 0.692 (6) |
C23A | 0.0965 (9) | −0.0943 (9) | 0.3306 (2) | 0.250 (4) | 0.692 (6) |
H23A | 0.0277 | −0.0830 | 0.3250 | 0.300* | 0.692 (6) |
H23B | 0.1261 | −0.0117 | 0.3185 | 0.300* | 0.692 (6) |
C24A | 0.1261 (7) | −0.2275 (10) | 0.3103 (3) | 0.231 (4) | 0.692 (6) |
H24A | 0.1177 | −0.2188 | 0.2768 | 0.347* | 0.692 (6) |
H24B | 0.0879 | −0.3050 | 0.3187 | 0.347* | 0.692 (6) |
H24C | 0.1921 | −0.2458 | 0.3220 | 0.347* | 0.692 (6) |
N1B | 0.459 (2) | 0.187 (4) | 1.0011 (6) | 0.194 (12)* | 0.308 (6) |
C1B | 0.4572 (10) | 0.1627 (15) | 0.9629 (3) | 0.087 (3)* | 0.308 (6) |
C2B | 0.441 (2) | 0.1329 (12) | 0.9143 (3) | 0.088 (6)* | 0.308 (6) |
C3B | 0.4330 (17) | −0.0078 (13) | 0.8999 (4) | 0.090 (7)* | 0.308 (6) |
H3BA | 0.4409 | −0.0813 | 0.9218 | 0.108* | 0.308 (6) |
C4B | 0.4144 (10) | −0.0374 (12) | 0.8545 (3) | 0.077 (4)* | 0.308 (6) |
H4BA | 0.4156 | −0.1316 | 0.8444 | 0.092* | 0.308 (6) |
C5B | 0.393 (4) | 0.0715 (14) | 0.8222 (4) | 0.095 (12)* | 0.308 (6) |
C6B | 0.379 (2) | 0.0423 (19) | 0.7750 (4) | 0.149 (11)* | 0.308 (6) |
H6BA | 0.3777 | −0.0518 | 0.7647 | 0.179* | 0.308 (6) |
C7B | 0.366 (2) | 0.1472 (15) | 0.7444 (4) | 0.099 (9)* | 0.308 (6) |
C8B | 0.3689 (13) | 0.2883 (13) | 0.7582 (4) | 0.094 (5)* | 0.308 (6) |
H8BA | 0.3570 | 0.3608 | 0.7360 | 0.112* | 0.308 (6) |
C9B | 0.3894 (12) | 0.3195 (13) | 0.8036 (4) | 0.093 (5)* | 0.308 (6) |
H9BA | 0.3970 | 0.4144 | 0.8129 | 0.112* | 0.308 (6) |
C10B | 0.399 (3) | 0.2120 (13) | 0.8370 (4) | 0.088 (6)* | 0.308 (6) |
C11B | 0.4239 (11) | 0.2405 (12) | 0.8838 (3) | 0.080 (4)* | 0.308 (6) |
H11B | 0.4289 | 0.3346 | 0.8943 | 0.096* | 0.308 (6) |
O1B | 0.3470 (9) | 0.116 (2) | 0.6980 (4) | 0.148 (9)* | 0.308 (6) |
O2B | 0.1958 (7) | 0.1460 (11) | 0.6993 (3) | 0.103 (3)* | 0.308 (6) |
C12B | 0.2563 (6) | 0.1302 (17) | 0.6760 (3) | 0.068 (3)* | 0.308 (6) |
C13B | 0.2474 (8) | 0.111 (3) | 0.6263 (3) | 0.085 (5)* | 0.308 (6) |
C14B | 0.3233 (8) | 0.0828 (13) | 0.6055 (3) | 0.110 (5)* | 0.308 (6) |
H14B | 0.3838 | 0.0751 | 0.6231 | 0.132* | 0.308 (6) |
C15B | 0.3109 (8) | 0.0656 (17) | 0.5587 (4) | 0.144 (6)* | 0.308 (6) |
H15B | 0.3636 | 0.0436 | 0.5444 | 0.173* | 0.308 (6) |
C16B | 0.2255 (8) | 0.0793 (15) | 0.5321 (3) | 0.122 (5)* | 0.308 (6) |
C17B | 0.1482 (10) | 0.092 (4) | 0.5540 (5) | 0.131 (9)* | 0.308 (6) |
H17B | 0.0871 | 0.0862 | 0.5369 | 0.157* | 0.308 (6) |
C18B | 0.1600 (7) | 0.1134 (19) | 0.6002 (4) | 0.084 (4)* | 0.308 (6) |
H18B | 0.1068 | 0.1302 | 0.6147 | 0.101* | 0.308 (6) |
C19B | 0.2193 (12) | 0.0783 (14) | 0.4804 (4) | 0.176 (6)* | 0.308 (6) |
H19C | 0.1846 | 0.1624 | 0.4678 | 0.211* | 0.308 (6) |
H19D | 0.2832 | 0.0841 | 0.4726 | 0.211* | 0.308 (6) |
C20B | 0.1719 (10) | −0.0493 (14) | 0.4583 (4) | 0.150 (4)* | 0.308 (6) |
H20C | 0.1042 | −0.0435 | 0.4599 | 0.180* | 0.308 (6) |
H20D | 0.1969 | −0.1329 | 0.4758 | 0.180* | 0.308 (6) |
C21B | 0.1845 (9) | −0.068 (2) | 0.4092 (4) | 0.197 (7)* | 0.308 (6) |
H21C | 0.2172 | 0.0170 | 0.4005 | 0.237* | 0.308 (6) |
H21D | 0.2280 | −0.1470 | 0.4083 | 0.237* | 0.308 (6) |
C22B | 0.1034 (8) | −0.0921 (19) | 0.3719 (4) | 0.169 (5)* | 0.308 (6) |
H22C | 0.0646 | −0.0066 | 0.3665 | 0.202* | 0.308 (6) |
H22D | 0.0638 | −0.1692 | 0.3804 | 0.202* | 0.308 (6) |
C23B | 0.1438 (8) | −0.130 (2) | 0.3296 (4) | 0.169 (5)* | 0.308 (6) |
H23D | 0.1818 | −0.0516 | 0.3204 | 0.202* | 0.308 (6) |
H23E | 0.1836 | −0.2140 | 0.3349 | 0.202* | 0.308 (6) |
C24B | 0.0605 (9) | −0.157 (2) | 0.2937 (4) | 0.180 (6)* | 0.308 (6) |
H24D | 0.0815 | −0.1898 | 0.2656 | 0.270* | 0.308 (6) |
H24G | 0.0247 | −0.0701 | 0.2873 | 0.270* | 0.308 (6) |
H24E | 0.0208 | −0.2281 | 0.3048 | 0.270* | 0.308 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1A | 0.162 (5) | 0.174 (5) | 0.093 (3) | −0.048 (4) | 0.003 (2) | −0.042 (2) |
C1A | 0.165 (6) | 0.177 (8) | 0.137 (5) | −0.058 (5) | 0.011 (4) | −0.031 (4) |
C2A | 0.112 (6) | 0.146 (7) | 0.104 (4) | −0.031 (3) | 0.011 (2) | −0.025 (3) |
C3A | 0.132 (7) | 0.131 (6) | 0.105 (4) | −0.023 (3) | 0.000 (2) | −0.005 (2) |
C4A | 0.143 (6) | 0.111 (4) | 0.131 (5) | −0.009 (3) | 0.004 (3) | −0.014 (2) |
C5A | 0.080 (4) | 0.103 (6) | 0.100 (6) | −0.0027 (15) | 0.011 (2) | −0.0106 (19) |
C6A | 0.082 (2) | 0.097 (3) | 0.091 (3) | 0.0071 (14) | 0.0105 (14) | −0.0054 (15) |
C7A | 0.095 (5) | 0.146 (8) | 0.098 (5) | 0.012 (3) | 0.0154 (19) | −0.001 (2) |
C8A | 0.161 (7) | 0.145 (6) | 0.155 (6) | −0.005 (3) | 0.018 (4) | 0.038 (4) |
C9A | 0.173 (7) | 0.106 (4) | 0.156 (7) | −0.017 (3) | 0.015 (4) | 0.008 (3) |
C10A | 0.097 (6) | 0.106 (5) | 0.125 (5) | −0.015 (2) | 0.019 (3) | −0.011 (2) |
C11A | 0.140 (5) | 0.119 (4) | 0.149 (6) | −0.038 (3) | 0.016 (3) | −0.036 (3) |
O1A | 0.0883 (19) | 0.176 (5) | 0.084 (2) | 0.0302 (17) | 0.0133 (10) | 0.0084 (14) |
O2A | 0.110 (2) | 0.135 (3) | 0.108 (2) | 0.0322 (19) | 0.0273 (16) | 0.014 (2) |
C12A | 0.113 (4) | 0.118 (4) | 0.140 (6) | 0.019 (2) | 0.034 (3) | 0.027 (3) |
C13A | 0.104 (3) | 0.091 (5) | 0.103 (4) | 0.017 (2) | 0.0192 (19) | 0.018 (2) |
C14A | 0.111 (3) | 0.125 (4) | 0.099 (3) | 0.027 (3) | 0.0207 (18) | 0.013 (2) |
C15A | 0.127 (3) | 0.153 (5) | 0.100 (3) | 0.041 (3) | 0.022 (2) | 0.008 (2) |
C16A | 0.142 (4) | 0.122 (4) | 0.100 (3) | 0.028 (3) | 0.015 (2) | 0.003 (2) |
C17A | 0.126 (5) | 0.152 (7) | 0.114 (4) | 0.033 (3) | −0.018 (3) | 0.002 (3) |
C18A | 0.125 (4) | 0.144 (5) | 0.140 (6) | 0.034 (3) | 0.018 (3) | 0.000 (4) |
C19A | 0.177 (5) | 0.216 (8) | 0.113 (4) | 0.050 (5) | −0.004 (3) | −0.025 (4) |
C20A | 0.286 (9) | 0.192 (7) | 0.111 (4) | 0.000 (6) | 0.015 (4) | 0.012 (4) |
C21A | 0.174 (5) | 0.251 (9) | 0.115 (4) | 0.001 (6) | 0.011 (3) | 0.006 (4) |
C22A | 0.297 (9) | 0.307 (10) | 0.127 (4) | 0.007 (7) | −0.028 (4) | 0.004 (4) |
C23A | 0.297 (9) | 0.307 (10) | 0.127 (4) | 0.007 (7) | −0.028 (4) | 0.004 (4) |
C24A | 0.258 (9) | 0.285 (11) | 0.156 (6) | 0.028 (8) | 0.048 (6) | −0.035 (6) |
N1A—C1A | 1.146 (6) | N1B—C1B | 1.148 (9) |
C1A—C2A | 1.449 (5) | C1B—C2B | 1.446 (7) |
C2A—C11A | 1.358 (6) | C2B—C11B | 1.364 (7) |
C2A—C3A | 1.408 (6) | C2B—C3B | 1.411 (8) |
C3A—C4A | 1.356 (5) | C3B—C4B | 1.356 (7) |
C3A—H3AA | 0.9500 | C3B—H3BA | 0.9500 |
C4A—C5A | 1.411 (6) | C4B—C5B | 1.415 (8) |
C4A—H4AA | 0.9500 | C4B—H4BA | 0.9500 |
C5A—C6A | 1.406 (5) | C5B—C6B | 1.405 (8) |
C5A—C10A | 1.413 (5) | C5B—C10B | 1.412 (7) |
C6A—C7A | 1.343 (5) | C6B—C7B | 1.342 (8) |
C6A—H6AA | 0.9500 | C6B—H6BA | 0.9500 |
C7A—O1A | 1.389 (5) | C7B—O1B | 1.388 (8) |
C7A—C8A | 1.406 (6) | C7B—C8B | 1.407 (8) |
C8A—C9A | 1.358 (6) | C8B—C9B | 1.361 (8) |
C8A—H8AA | 0.9500 | C8B—H8BA | 0.9500 |
C9A—C10A | 1.414 (6) | C9B—C10B | 1.417 (8) |
C9A—H9AA | 0.9500 | C9B—H9BA | 0.9500 |
C10A—C11A | 1.397 (6) | C10B—C11B | 1.399 (8) |
C11A—H11A | 0.9500 | C11B—H11B | 0.9500 |
O1A—C12A | 1.375 (5) | O1B—C12B | 1.377 (8) |
O2A—C12A | 1.204 (5) | O2B—C12B | 1.204 (7) |
C12A—C13A | 1.473 (6) | C12B—C13B | 1.465 (8) |
C13A—C14A | 1.365 (5) | C13B—C14B | 1.366 (8) |
C13A—C18A | 1.374 (5) | C13B—C18B | 1.375 (7) |
C14A—C15A | 1.375 (5) | C14B—C15B | 1.377 (8) |
C14A—H14A | 0.9500 | C14B—H14B | 0.9500 |
C15A—C16A | 1.367 (5) | C15B—C16B | 1.365 (9) |
C15A—H15A | 0.9500 | C15B—H15B | 0.9500 |
C16A—C17A | 1.380 (7) | C16B—C17B | 1.382 (10) |
C16A—C19A | 1.510 (6) | C16B—C19B | 1.513 (9) |
C17A—C18A | 1.363 (7) | C17B—C18B | 1.366 (9) |
C17A—H17A | 0.9500 | C17B—H17B | 0.9500 |
C18A—H18A | 0.9500 | C18B—H18B | 0.9500 |
C19A—C20A | 1.438 (7) | C19B—C20B | 1.4992 (11) |
C19A—H19A | 0.9900 | C19B—H19C | 0.9900 |
C19A—H19B | 0.9900 | C19B—H19D | 0.9900 |
C20A—C21A | 1.485 (6) | C20B—C21B | 1.4998 (11) |
C20A—H20A | 0.9900 | C20B—H20C | 0.9900 |
C20A—H20B | 0.9900 | C20B—H20D | 0.9900 |
C21A—C22A | 1.476 (8) | C21B—C22B | 1.4990 (11) |
C21A—H21A | 0.9900 | C21B—H21C | 0.9900 |
C21A—H21B | 0.9900 | C21B—H21D | 0.9900 |
C22A—C23A | 1.574 (7) | C22B—C23B | 1.5011 (11) |
C22A—H22A | 0.9900 | C22B—H22C | 0.9900 |
C22A—H22B | 0.9900 | C22B—H22D | 0.9900 |
C23A—C24A | 1.4984 (11) | C23B—C24B | 1.4995 (11) |
C23A—H23A | 0.9900 | C23B—H23D | 0.9900 |
C23A—H23B | 0.9900 | C23B—H23E | 0.9900 |
C24A—H24A | 0.9800 | C24B—H24D | 0.9800 |
C24A—H24B | 0.9800 | C24B—H24G | 0.9800 |
C24A—H24C | 0.9800 | C24B—H24E | 0.9800 |
N1A—C1A—C2A | 174.0 (11) | C3B—C2B—C1B | 118.7 (8) |
C11A—C2A—C3A | 120.1 (5) | C4B—C3B—C2B | 119.4 (8) |
C11A—C2A—C1A | 119.2 (6) | C4B—C3B—H3BA | 120.3 |
C3A—C2A—C1A | 120.5 (6) | C2B—C3B—H3BA | 120.3 |
C4A—C3A—C2A | 119.1 (5) | C3B—C4B—C5B | 120.3 (8) |
C4A—C3A—H3AA | 120.5 | C3B—C4B—H4BA | 119.9 |
C2A—C3A—H3AA | 120.5 | C5B—C4B—H4BA | 119.9 |
C3A—C4A—C5A | 122.0 (6) | C6B—C5B—C10B | 119.3 (8) |
C3A—C4A—H4AA | 119.0 | C6B—C5B—C4B | 120.6 (10) |
C5A—C4A—H4AA | 119.0 | C10B—C5B—C4B | 119.5 (8) |
C6A—C5A—C4A | 122.4 (5) | C7B—C6B—C5B | 120.2 (10) |
C6A—C5A—C10A | 119.1 (4) | C7B—C6B—H6BA | 119.9 |
C4A—C5A—C10A | 118.4 (5) | C5B—C6B—H6BA | 119.9 |
C7A—C6A—C5A | 120.1 (4) | C6B—C7B—O1B | 119.5 (10) |
C7A—C6A—H6AA | 119.9 | C6B—C7B—C8B | 121.8 (9) |
C5A—C6A—H6AA | 119.9 | O1B—C7B—C8B | 118.8 (9) |
C6A—C7A—O1A | 120.0 (6) | C9B—C8B—C7B | 119.1 (8) |
C6A—C7A—C8A | 122.2 (5) | C9B—C8B—H8BA | 120.4 |
O1A—C7A—C8A | 117.5 (5) | C7B—C8B—H8BA | 120.4 |
C9A—C8A—C7A | 118.7 (6) | C8B—C9B—C10B | 120.7 (8) |
C9A—C8A—H8AA | 120.6 | C8B—C9B—H9BA | 119.6 |
C7A—C8A—H8AA | 120.6 | C10B—C9B—H9BA | 119.6 |
C8A—C9A—C10A | 121.2 (6) | C11B—C10B—C5B | 119.1 (7) |
C8A—C9A—H9AA | 119.4 | C11B—C10B—C9B | 122.0 (9) |
C10A—C9A—H9AA | 119.4 | C5B—C10B—C9B | 118.6 (7) |
C11A—C10A—C5A | 118.4 (5) | C2B—C11B—C10B | 119.9 (8) |
C11A—C10A—C9A | 122.7 (6) | C2B—C11B—H11B | 120.1 |
C5A—C10A—C9A | 118.6 (5) | C10B—C11B—H11B | 120.1 |
C2A—C11A—C10A | 121.9 (5) | C12B—O1B—C7B | 118.1 (13) |
C2A—C11A—H11A | 119.0 | O2B—C12B—O1B | 117.8 (9) |
C10A—C11A—H11A | 119.0 | O2B—C12B—C13B | 129.0 (8) |
C12A—O1A—C7A | 118.6 (6) | O1B—C12B—C13B | 113.0 (7) |
O2A—C12A—O1A | 120.4 (5) | C14B—C13B—C18B | 119.0 (7) |
O2A—C12A—C13A | 126.7 (5) | C14B—C13B—C12B | 121.6 (7) |
O1A—C12A—C13A | 112.9 (5) | C18B—C13B—C12B | 119.3 (8) |
C14A—C13A—C18A | 118.7 (5) | C13B—C14B—C15B | 119.2 (9) |
C14A—C13A—C12A | 122.8 (4) | C13B—C14B—H14B | 120.4 |
C18A—C13A—C12A | 118.4 (5) | C15B—C14B—H14B | 120.4 |
C13A—C14A—C15A | 119.8 (4) | C16B—C15B—C14B | 122.1 (9) |
C13A—C14A—H14A | 120.1 | C16B—C15B—H15B | 118.9 |
C15A—C14A—H14A | 120.1 | C14B—C15B—H15B | 118.9 |
C16A—C15A—C14A | 122.3 (4) | C15B—C16B—C17B | 117.7 (8) |
C16A—C15A—H15A | 118.8 | C15B—C16B—C19B | 119.1 (9) |
C14A—C15A—H15A | 118.8 | C17B—C16B—C19B | 123.1 (9) |
C15A—C16A—C17A | 117.1 (4) | C18B—C17B—C16B | 119.8 (10) |
C15A—C16A—C19A | 119.8 (4) | C18B—C17B—H17B | 120.1 |
C17A—C16A—C19A | 123.1 (4) | C16B—C17B—H17B | 120.1 |
C18A—C17A—C16A | 121.1 (5) | C17B—C18B—C13B | 121.3 (9) |
C18A—C17A—H17A | 119.4 | C17B—C18B—H18B | 119.4 |
C16A—C17A—H17A | 119.4 | C13B—C18B—H18B | 119.4 |
C17A—C18A—C13A | 120.9 (6) | C20B—C19B—C16B | 113.4 (9) |
C17A—C18A—H18A | 119.5 | C20B—C19B—H19C | 108.9 |
C13A—C18A—H18A | 119.5 | C16B—C19B—H19C | 108.9 |
C20A—C19A—C16A | 117.4 (5) | C20B—C19B—H19D | 108.9 |
C20A—C19A—H19A | 107.9 | C16B—C19B—H19D | 108.9 |
C16A—C19A—H19A | 107.9 | H19C—C19B—H19D | 107.7 |
C20A—C19A—H19B | 107.9 | C19B—C20B—C21B | 113.6 (9) |
C16A—C19A—H19B | 107.9 | C19B—C20B—H20C | 108.8 |
H19A—C19A—H19B | 107.2 | C21B—C20B—H20C | 108.8 |
C19A—C20A—C21A | 118.0 (6) | C19B—C20B—H20D | 108.8 |
C19A—C20A—H20A | 107.8 | C21B—C20B—H20D | 108.8 |
C21A—C20A—H20A | 107.8 | H20C—C20B—H20D | 107.7 |
C19A—C20A—H20B | 107.8 | C22B—C21B—C20B | 122.1 (10) |
C21A—C20A—H20B | 107.8 | C22B—C21B—H21C | 106.8 |
H20A—C20A—H20B | 107.2 | C20B—C21B—H21C | 106.8 |
C22A—C21A—C20A | 118.6 (6) | C22B—C21B—H21D | 106.8 |
C22A—C21A—H21A | 107.7 | C20B—C21B—H21D | 106.8 |
C20A—C21A—H21A | 107.7 | H21C—C21B—H21D | 106.7 |
C22A—C21A—H21B | 107.7 | C21B—C22B—C23B | 106.7 (8) |
C20A—C21A—H21B | 107.7 | C21B—C22B—H22C | 110.4 |
H21A—C21A—H21B | 107.1 | C23B—C22B—H22C | 110.4 |
C21A—C22A—C23A | 101.6 (6) | C21B—C22B—H22D | 110.4 |
C21A—C22A—H22A | 111.4 | C23B—C22B—H22D | 110.4 |
C23A—C22A—H22A | 111.4 | H22C—C22B—H22D | 108.6 |
C21A—C22A—H22B | 111.4 | C24B—C23B—C22B | 104.8 (8) |
C23A—C22A—H22B | 111.4 | C24B—C23B—H23D | 110.8 |
H22A—C22A—H22B | 109.3 | C22B—C23B—H23D | 110.8 |
C24A—C23A—C22A | 101.0 (6) | C24B—C23B—H23E | 110.8 |
C24A—C23A—H23A | 111.6 | C22B—C23B—H23E | 110.8 |
C22A—C23A—H23A | 111.6 | H23D—C23B—H23E | 108.9 |
C24A—C23A—H23B | 111.6 | C23B—C24B—H24D | 109.5 |
C22A—C23A—H23B | 111.6 | C23B—C24B—H24G | 109.5 |
H23A—C23A—H23B | 109.4 | H24D—C24B—H24G | 109.5 |
N1B—C1B—C2B | 172 (2) | C23B—C24B—H24E | 109.5 |
C11B—C2B—C3B | 121.5 (8) | H24D—C24B—H24E | 109.5 |
C11B—C2B—C1B | 119.5 (8) | H24G—C24B—H24E | 109.5 |
C11A—C2A—C3A—C4A | −3 (2) | C11B—C2B—C3B—C4B | 4 (4) |
C1A—C2A—C3A—C4A | −178.5 (13) | C1B—C2B—C3B—C4B | 178 (2) |
C2A—C3A—C4A—C5A | 3 (2) | C2B—C3B—C4B—C5B | −7 (4) |
C3A—C4A—C5A—C6A | −177.4 (15) | C3B—C4B—C5B—C6B | 177 (3) |
C3A—C4A—C5A—C10A | −2 (3) | C3B—C4B—C5B—C10B | 6 (6) |
C4A—C5A—C6A—C7A | 175.3 (16) | C10B—C5B—C6B—C7B | −4 (6) |
C10A—C5A—C6A—C7A | 0 (3) | C4B—C5B—C6B—C7B | −175 (3) |
C5A—C6A—C7A—O1A | 174.3 (13) | C5B—C6B—C7B—O1B | −177 (3) |
C5A—C6A—C7A—C8A | 1 (2) | C5B—C6B—C7B—C8B | 2 (5) |
C6A—C7A—C8A—C9A | −2 (2) | C6B—C7B—C8B—C9B | 3 (4) |
O1A—C7A—C8A—C9A | −175.7 (12) | O1B—C7B—C8B—C9B | −178.5 (19) |
C7A—C8A—C9A—C10A | 3 (2) | C7B—C8B—C9B—C10B | −5 (4) |
C6A—C5A—C10A—C11A | 175.4 (16) | C6B—C5B—C10B—C11B | −173 (4) |
C4A—C5A—C10A—C11A | 0 (3) | C4B—C5B—C10B—C11B | −2 (7) |
C6A—C5A—C10A—C9A | 1 (3) | C6B—C5B—C10B—C9B | 1 (7) |
C4A—C5A—C10A—C9A | −174.6 (16) | C4B—C5B—C10B—C9B | 172 (3) |
C8A—C9A—C10A—C11A | −176.5 (16) | C8B—C9B—C10B—C11B | 178 (3) |
C8A—C9A—C10A—C5A | −2 (3) | C8B—C9B—C10B—C5B | 4 (5) |
C3A—C2A—C11A—C10A | 1 (3) | C3B—C2B—C11B—C10B | −1 (4) |
C1A—C2A—C11A—C10A | 176.5 (15) | C1B—C2B—C11B—C10B | −174 (3) |
C5A—C10A—C11A—C2A | 1 (3) | C5B—C10B—C11B—C2B | 0 (5) |
C9A—C10A—C11A—C2A | 174.8 (16) | C9B—C10B—C11B—C2B | −174 (3) |
C6A—C7A—O1A—C12A | 110.0 (13) | C6B—C7B—O1B—C12B | 103 (3) |
C8A—C7A—O1A—C12A | −76.0 (16) | C8B—C7B—O1B—C12B | −75 (3) |
C7A—O1A—C12A—O2A | 3.8 (16) | C7B—O1B—C12B—O2B | −12 (2) |
C7A—O1A—C12A—C13A | −177.7 (9) | C7B—O1B—C12B—C13B | 173.2 (17) |
O2A—C12A—C13A—C14A | −178.4 (11) | O2B—C12B—C13B—C14B | −174.5 (18) |
O1A—C12A—C13A—C14A | 3.2 (17) | O1B—C12B—C13B—C14B | 0 (3) |
O2A—C12A—C13A—C18A | 4 (2) | O2B—C12B—C13B—C18B | 2 (4) |
O1A—C12A—C13A—C18A | −174.6 (11) | O1B—C12B—C13B—C18B | 176 (2) |
C18A—C13A—C14A—C15A | −1.2 (15) | C18B—C13B—C14B—C15B | 4 (3) |
C12A—C13A—C14A—C15A | −178.9 (10) | C12B—C13B—C14B—C15B | 180.0 (18) |
C13A—C14A—C15A—C16A | −0.1 (12) | C13B—C14B—C15B—C16B | 2 (2) |
C14A—C15A—C16A—C17A | 1.6 (13) | C14B—C15B—C16B—C17B | −9 (3) |
C14A—C15A—C16A—C19A | −179.1 (7) | C14B—C15B—C16B—C19B | 171.8 (12) |
C15A—C16A—C17A—C18A | −2 (2) | C15B—C16B—C17B—C18B | 10 (4) |
C19A—C16A—C17A—C18A | 178.8 (12) | C19B—C16B—C17B—C18B | −170 (2) |
C16A—C17A—C18A—C13A | 1 (2) | C16B—C17B—C18B—C13B | −5 (5) |
C14A—C13A—C18A—C17A | 1 (2) | C14B—C13B—C18B—C17B | −2 (4) |
C12A—C13A—C18A—C17A | 178.7 (14) | C12B—C13B—C18B—C17B | −178 (3) |
C15A—C16A—C19A—C20A | −148.2 (8) | C15B—C16B—C19B—C20B | 111.4 (16) |
C17A—C16A—C19A—C20A | 31.1 (15) | C17B—C16B—C19B—C20B | −68 (3) |
C16A—C19A—C20A—C21A | 173.8 (6) | C16B—C19B—C20B—C21B | −166.8 (12) |
C19A—C20A—C21A—C22A | 54.9 (12) | C19B—C20B—C21B—C22B | −129.0 (19) |
C20A—C21A—C22A—C23A | 156.5 (8) | C20B—C21B—C22B—C23B | −170.5 (17) |
C21A—C22A—C23A—C24A | 149.9 (9) | C21B—C22B—C23B—C24B | 178.6 (14) |
Cg1 and Cg2 are the centroids of the C2A–C5A/C10A/C11A and C13B–C18B rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C4A—H4AA···O2Ai | 0.95 | 2.44 | 3.303 (11) | 149 |
C9B—H9BA···O2Bii | 0.95 | 2.59 | 3.352 (11) | 138 |
C14B—H14B···Cg1iii | 0.95 | 2.85 | 3.708 (14) | 151 |
C20A—H20A···Cg2iv | 0.99 | 2.91 | 3.819 (14) | 152 |
C19B—H19C···Cg2iv | 0.99 | 2.88 | 3.746 (19) | 146 |
Symmetry codes: (i) −x+1/2, y−1/2, −z+3/2; (ii) −x+1/2, y+1/2, −z+3/2; (iii) −x+1, y, −z+3/2; (iv) −x+1/2, −y+1/2, −z+1. |
Cg1 and Cg2 are the centroids of the C2A–C5A/C10A/C11A and C13B–C18B rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C4A—H4AA···O2Ai | 0.95 | 2.44 | 3.303 (11) | 149 |
C9B—H9BA···O2Bii | 0.95 | 2.59 | 3.352 (11) | 138 |
C14B—H14B···Cg1iii | 0.95 | 2.85 | 3.708 (14) | 151 |
C20A—H20A···Cg2iv | 0.99 | 2.91 | 3.819 (14) | 152 |
C19B—H19C···Cg2iv | 0.99 | 2.88 | 3.746 (19) | 146 |
Symmetry codes: (i) −x+1/2, y−1/2, −z+3/2; (ii) −x+1/2, y+1/2, −z+3/2; (iii) −x+1, y, −z+3/2; (iv) −x+1/2, −y+1/2, −z+1. |
Acknowledgements
This research was supported by a PRGS Research Grant (No. RDU 130803).
References
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–S19. CrossRef Web of Science Google Scholar
Blake, A. J., Fallis, I. A., Parsons, S., Schröder, M. & Bruce, D. W. (1995). Acta Cryst. C51, 2666–2668. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Coates, D. & Gray, G. W. (1976). Mol. Cryst. Liq. Cryst. 37, 249–262. CrossRef CAS Google Scholar
Cox, R. J. & Clecak, N. J. (1976). Mol. Cryst. Liq. Cryst. 37, 263–267. CrossRef CAS Google Scholar
Hanasaki, T., Kamei, Y., Mandai, A., Uno, K. & Kaneko, K. (2011). Liq. Cryst. 38, 785–792. CrossRef Google Scholar
Klingbiel, R. T., Genova, D. J., Crisewell, T. R. & Vanmeter, J. P. (1974). J. Am. Chem. Soc, 96, 7625–7631. CrossRef Google Scholar
Kuzmina, L. G., Pestov, S. M., Kochetov, A. N., Churakov, A. V. & Lermontova, E. K. (2010). Crystallogr. Rep. 55, 786–792. CAS Google Scholar
Li, Y.-H. (2006). Acta Cryst. E62, o5935–o5936. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Reddy, R. A. & Tschierske, C. (2006). J. Mater. Chem. 16, 907–961. CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Takezoe, H. & Takanishi, Y. (2006). Jpn. J. Appl. Phys. 45, 597–625. CrossRef CAS Google Scholar
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Electro-optical display devices require certain desirable features such as large positive dielectric anisotropy, nematic phase, low melting point, stability and lack of color (Cox & Clecak, 1976; Reddy & Tschierske, 2006; Hanasaki et al., 2011). To obtain such properties, a highly polar terminal cyano group can be incorporated to give a large dipole moment. Maximum dipole moment (90 degrees) indicates that the dipole moment is exactly parallel to the molecular short axis, which acts along the long axis of the molecule and helps to give the proper alignment for liquid crystal displays (Coates & Gray, 1976; Klingbiel et al., 1974; Takezoe & Takanishi, 2006). Here we report the synthesis and single-crystal X-ray study of an unsymmetrical naphthalene liquid crystal molecule. The shows a nematic phase after 379 K then a stable phase until an isotropic state at 411 K on a heating cycle. Upon cooling from the isotropic state, the nematic phase was reformed at 410 K, the phase is stabilized before crystallizes at 321 K.
The molecular structure of the title compound is shown in Fig 1. The whole molecule of the title compound is disordered over two positions with a refined site-occupancy ratio of 0.692 (6): 0.308 (6). For the major component, the naphthalene ring system (C2A—C11A) makes a dihedral angle of 68.6 (5)° with the benzene ring (C13A—C18A). In the minor component, the dihedral angle formed between the naphthalene ring system (C2B—C11B) and the benzene ring (C13B—C18B) is 81.6 (10)°. All the bond lengths (Allen et al., 1987) and angles are in normal ranges and compared with the closely related structures (Kuzmina et al., 2010; Blake et al., 1995; Li, 2006)
In the crystal, molecules are linked into chains propagating along the b-axis via weak C—H···O hydrogen bonds. Weak C—H···π interactions are also observed (see Table 1).