organic compounds
Ethyl 2-cyano-2-{(Z)-2-[2,2-dicyano-1-(4-methylphenyl)ethyl]cyclohexylidene}acetate
aDepartment of Chemistry, Annamalai University, Annamalainagar, Chidambaram 608 002, India, and bPG & Research Department of Physics, Government Arts College, Melur 625 106, India
*Correspondence e-mail: profmani.au@gmail.com
In the title compound, C22H23N3O2, the cyclohexane ring adopts a chair conformation. The methylphenyl ring is oriented at an angle of 36.2 (1)° with respect to the best plane of cyclohexane moiety. In the crystal, molecules associate via C—H⋯N hydrogen bonds, forming a three-dimensional network.
Keywords: crystal structure; cyclohexylidene derivatives; chair conformation; intermolecular C—H⋯N hydrogen bonds.
CCDC reference: 2057162
Structure description
Cyclohexylidene derivatives possess a wide range of biological activities including antibacterial (Gupta & Narayana, 1997), antiviral (Ulusoy Guzeldemirci et al., 2016), antituberculatic and anti-inflammatory (Kabir et al., 2008). As part of our studies in this area, we have undertaken a single-crystal X-ray diffraction study for the title compound, and the results are presented here.
The methylphenyl ring is oriented at an angle of 36.2 (1)° with respect to the best plane of cyclohexane moiety. The cyclohexane ring adopts a chair conformation, the puckering parameters (Cremer & Pople, 1975) are: q2 = 0.001 (1) Å, q3 = −0.562 (2) Å, QT = 0.562 (2) Å and θ = 179.0 (1)°. Atoms C1 and C4 deviate by 0.681 (1) and −0.652 (1) Å, respectively, from the least-squares plane through the remaining four atoms. An intramolecular C—H⋯O hydrogen bond is observed (Table 1), which generates an S(6) ring (Fig. 1).
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In the crystal, molecules associate via pairwise C5—H5A⋯N1i hydrogen bonds into inversion dimers with an R22(16) loop motif. In addition, C8—H8⋯N3ii hydrogen bonds form a R22(16) graph-set motif (Fig. 2).
The two-dimensional fingerprint plots (Spackman & Jayatilaka, 2009) of the molecule, created using Crystal Explorer 17 (Turner et al., 2017) for the contacts contributing to the Hirshfeld surface are shown in Figs. 3–5. The analysis reveals that H⋯H contacts (45.7%) and N⋯H/H⋯N contacts (29.8%) are the main contributors to the crystal packing, followed by C⋯H/H⋯C (14%) and O⋯H/H⋯O (7.8%) contacts.
Synthesis and crystallization
A mixture of 2-amino-4-(p-tolyl)octahydronaphthalene-1,3,3(2H)-tricarbonitrile (0.01 mol), formic acid (5 mL) and a catalytic amount of concentrated HCl was refluxed for 16 h and the reaction mixture was allowed to cool. The reaction mixture was poured onto crushed ice and the solid that separated was filtered, dried and recrystallized using ethanol and water as mixed solvents.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2Structural data
CCDC reference: 2057162
https://doi.org/10.1107/S2414314621005009/bt4111sup1.cif
contains datablocks I, shelx. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314621005009/bt4111Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314621005009/bt4111Isup3.cml
Data collection: SMART (Bruker, 2008); cell
SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2020); software used to prepare material for publication: SHELXL2018/3 (Sheldrick, 2015) and PLATON (Spek, 2020).C22H23N3O2 | Z = 2 |
Mr = 361.43 | F(000) = 384 |
Triclinic, P1 | Dx = 1.140 Mg m−3 |
a = 8.4465 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.2960 (4) Å | Cell parameters from 18428 reflections |
c = 12.1699 (4) Å | θ = 2.8–28.2° |
α = 91.240 (1)° | µ = 0.07 mm−1 |
β = 95.072 (1)° | T = 296 K |
γ = 92.102 (1)° | Block, colourless |
V = 1053.17 (7) Å3 | 0.24 × 0.21 × 0.19 mm |
Bruker SMART APEX CCD area-detector diffractometer | Rint = 0.033 |
Radiation source: fine-focus sealed tube | θmax = 30.0°, θmin = 2.6° |
ω and φ scans | h = −11→11 |
28133 measured reflections | k = −14→14 |
6098 independent reflections | l = −16→17 |
4212 reflections with I > 2σ(I) |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.064 | H-atom parameters constrained |
wR(F2) = 0.211 | w = 1/[σ2(Fo2) + (0.1037P)2 + 0.3202P] where P = (Fo2 + 2Fc2)/3 |
S = 0.97 | (Δ/σ)max < 0.001 |
6098 reflections | Δρmax = 0.38 e Å−3 |
244 parameters | Δρmin = −0.31 e Å−3 |
0 restraints |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. H atoms were placed in idealized positions and allowed to ride on their parent atoms: C—H = 0.93–0.98 Å, with Uiso(H) = 1.5Ueq(C) for methyl H atoms and 1.2Ueq(C) for other H atoms. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.2013 (2) | 0.55320 (15) | 0.86132 (11) | 0.0772 (4) | |
O2 | 0.0185 (2) | 0.42057 (16) | 0.77154 (13) | 0.0819 (5) | |
N1 | −0.1230 (3) | 1.0587 (2) | 0.60489 (18) | 0.0857 (6) | |
N2 | −0.0870 (3) | 0.7604 (3) | 0.8407 (2) | 0.1067 (8) | |
N3 | 0.11934 (19) | 0.34667 (15) | 0.52121 (14) | 0.0616 (4) | |
C1 | 0.30484 (18) | 0.75924 (14) | 0.70937 (13) | 0.0443 (3) | |
H1 | 0.285441 | 0.734845 | 0.784544 | 0.053* | |
C2 | 0.4861 (2) | 0.78324 (19) | 0.70392 (18) | 0.0628 (5) | |
H2A | 0.521171 | 0.859385 | 0.749172 | 0.075* | |
H2B | 0.541326 | 0.709455 | 0.734562 | 0.075* | |
C3 | 0.5315 (2) | 0.8033 (2) | 0.5874 (2) | 0.0732 (6) | |
H3A | 0.486124 | 0.882452 | 0.559229 | 0.088* | |
H3B | 0.646316 | 0.813127 | 0.588507 | 0.088* | |
C4 | 0.4726 (2) | 0.6896 (2) | 0.5118 (2) | 0.0700 (5) | |
H4A | 0.528715 | 0.612669 | 0.534317 | 0.084* | |
H4B | 0.495422 | 0.708172 | 0.436902 | 0.084* | |
C5 | 0.2929 (2) | 0.66303 (15) | 0.51486 (13) | 0.0489 (4) | |
H5A | 0.235573 | 0.735033 | 0.482858 | 0.059* | |
H5B | 0.260103 | 0.585006 | 0.471424 | 0.059* | |
C6 | 0.25320 (16) | 0.64621 (13) | 0.63136 (12) | 0.0411 (3) | |
C7 | 0.21454 (17) | 0.88396 (13) | 0.68062 (12) | 0.0417 (3) | |
H7 | 0.244434 | 0.910752 | 0.608248 | 0.050* | |
C8 | 0.03147 (19) | 0.85589 (15) | 0.66844 (14) | 0.0488 (4) | |
H8 | 0.009240 | 0.789898 | 0.609301 | 0.059* | |
C9 | −0.0339 (2) | 0.8042 (2) | 0.76680 (19) | 0.0646 (5) | |
C10 | −0.0551 (2) | 0.97122 (18) | 0.63408 (15) | 0.0576 (4) | |
C11 | 0.26493 (18) | 0.99501 (14) | 0.76145 (12) | 0.0440 (3) | |
C12 | 0.2656 (3) | 0.98255 (17) | 0.87475 (14) | 0.0602 (5) | |
H12 | 0.231616 | 0.904205 | 0.903138 | 0.072* | |
C13 | 0.3163 (3) | 1.08555 (19) | 0.94631 (15) | 0.0662 (5) | |
H13 | 0.315364 | 1.074856 | 1.021940 | 0.079* | |
C14 | 0.3677 (2) | 1.20274 (18) | 0.90808 (16) | 0.0602 (5) | |
C15 | 0.3642 (3) | 1.21591 (18) | 0.79527 (17) | 0.0660 (5) | |
H15 | 0.397002 | 1.294798 | 0.767239 | 0.079* | |
C16 | 0.3129 (2) | 1.11375 (16) | 0.72261 (15) | 0.0563 (4) | |
H16 | 0.310842 | 1.125603 | 0.646965 | 0.068* | |
C17 | 0.4252 (3) | 1.3131 (2) | 0.9871 (2) | 0.0852 (7) | |
H17A | 0.456292 | 1.387009 | 0.946141 | 0.128* | |
H17B | 0.341186 | 1.335986 | 1.031229 | 0.128* | |
H17C | 0.514778 | 1.286442 | 1.034240 | 0.128* | |
C18 | 0.18375 (18) | 0.53484 (14) | 0.66384 (12) | 0.0437 (3) | |
C19 | 0.14525 (18) | 0.43040 (14) | 0.58413 (13) | 0.0461 (3) | |
C20 | 0.1382 (2) | 0.50714 (16) | 0.77718 (15) | 0.0548 (4) | |
C21 | −0.0385 (4) | 0.3775 (3) | 0.8773 (3) | 0.1121 (11) | |
H21A | 0.051164 | 0.353762 | 0.927149 | 0.135* | |
H21B | −0.090609 | 0.448219 | 0.911649 | 0.135* | |
C22 | −0.1466 (7) | 0.2695 (6) | 0.8578 (4) | 0.230 (4) | |
H22A | −0.182981 | 0.242201 | 0.926523 | 0.345* | |
H22B | −0.235819 | 0.293629 | 0.809141 | 0.345* | |
H22C | −0.094368 | 0.199386 | 0.824606 | 0.345* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.1095 (12) | 0.0724 (9) | 0.0462 (7) | −0.0169 (8) | −0.0038 (7) | 0.0028 (6) |
O2 | 0.0936 (11) | 0.0866 (10) | 0.0649 (9) | −0.0352 (9) | 0.0220 (8) | −0.0082 (7) |
N1 | 0.0845 (13) | 0.0805 (12) | 0.0916 (14) | 0.0291 (10) | −0.0066 (10) | 0.0086 (10) |
N2 | 0.0828 (14) | 0.1213 (19) | 0.122 (2) | 0.0053 (13) | 0.0354 (14) | 0.0376 (16) |
N3 | 0.0638 (9) | 0.0504 (8) | 0.0681 (10) | −0.0032 (6) | −0.0017 (7) | −0.0148 (7) |
C1 | 0.0461 (7) | 0.0394 (7) | 0.0454 (7) | −0.0001 (5) | −0.0041 (6) | −0.0053 (6) |
C2 | 0.0452 (8) | 0.0555 (9) | 0.0841 (13) | 0.0001 (7) | −0.0095 (8) | −0.0148 (9) |
C3 | 0.0482 (9) | 0.0661 (11) | 0.1056 (17) | −0.0106 (8) | 0.0168 (10) | −0.0112 (11) |
C4 | 0.0612 (11) | 0.0656 (11) | 0.0858 (14) | −0.0039 (9) | 0.0272 (10) | −0.0125 (10) |
C5 | 0.0544 (9) | 0.0440 (7) | 0.0484 (8) | −0.0004 (6) | 0.0087 (6) | −0.0049 (6) |
C6 | 0.0386 (7) | 0.0381 (6) | 0.0454 (7) | 0.0034 (5) | −0.0021 (5) | −0.0044 (5) |
C7 | 0.0458 (7) | 0.0383 (7) | 0.0396 (7) | −0.0001 (5) | −0.0014 (5) | −0.0057 (5) |
C8 | 0.0475 (8) | 0.0433 (7) | 0.0537 (9) | 0.0030 (6) | −0.0040 (6) | −0.0112 (6) |
C9 | 0.0506 (9) | 0.0612 (10) | 0.0824 (13) | 0.0027 (8) | 0.0066 (9) | 0.0061 (10) |
C10 | 0.0557 (9) | 0.0585 (10) | 0.0568 (10) | 0.0076 (8) | −0.0053 (7) | −0.0078 (8) |
C11 | 0.0475 (8) | 0.0391 (7) | 0.0439 (7) | 0.0001 (6) | −0.0020 (6) | −0.0071 (6) |
C12 | 0.0866 (13) | 0.0476 (8) | 0.0446 (8) | −0.0081 (8) | 0.0010 (8) | −0.0054 (7) |
C13 | 0.0893 (14) | 0.0608 (10) | 0.0457 (9) | −0.0025 (9) | −0.0044 (9) | −0.0133 (8) |
C14 | 0.0635 (10) | 0.0509 (9) | 0.0621 (10) | 0.0011 (7) | −0.0111 (8) | −0.0184 (8) |
C15 | 0.0853 (13) | 0.0431 (8) | 0.0664 (11) | −0.0135 (8) | −0.0021 (10) | −0.0064 (8) |
C16 | 0.0739 (11) | 0.0453 (8) | 0.0480 (8) | −0.0082 (7) | 0.0008 (8) | −0.0031 (7) |
C17 | 0.1015 (17) | 0.0665 (12) | 0.0806 (15) | −0.0079 (12) | −0.0192 (12) | −0.0301 (11) |
C18 | 0.0449 (7) | 0.0394 (7) | 0.0454 (7) | 0.0007 (5) | −0.0015 (6) | −0.0044 (6) |
C19 | 0.0447 (7) | 0.0409 (7) | 0.0515 (8) | 0.0009 (6) | −0.0005 (6) | −0.0028 (6) |
C20 | 0.0654 (10) | 0.0459 (8) | 0.0528 (9) | −0.0025 (7) | 0.0055 (8) | −0.0002 (7) |
C21 | 0.133 (3) | 0.122 (2) | 0.0823 (18) | −0.037 (2) | 0.0367 (17) | 0.0020 (16) |
C22 | 0.243 (6) | 0.294 (8) | 0.152 (4) | −0.161 (6) | 0.090 (4) | −0.004 (4) |
O1—C20 | 1.192 (2) | C8—C10 | 1.466 (2) |
O2—C20 | 1.320 (2) | C8—C9 | 1.465 (3) |
O2—C21 | 1.484 (3) | C8—H8 | 0.9800 |
N1—C10 | 1.132 (2) | C11—C16 | 1.380 (2) |
N2—C9 | 1.135 (3) | C11—C12 | 1.387 (2) |
N3—C19 | 1.143 (2) | C12—C13 | 1.388 (2) |
C1—C6 | 1.5125 (19) | C12—H12 | 0.9300 |
C1—C7 | 1.548 (2) | C13—C14 | 1.372 (3) |
C1—C2 | 1.550 (2) | C13—H13 | 0.9300 |
C1—H1 | 0.9800 | C14—C15 | 1.380 (3) |
C2—C3 | 1.518 (3) | C14—C17 | 1.511 (2) |
C2—H2A | 0.9700 | C15—C16 | 1.391 (2) |
C2—H2B | 0.9700 | C15—H15 | 0.9300 |
C3—C4 | 1.514 (3) | C16—H16 | 0.9300 |
C3—H3A | 0.9700 | C17—H17A | 0.9600 |
C3—H3B | 0.9700 | C17—H17B | 0.9600 |
C4—C5 | 1.537 (3) | C17—H17C | 0.9600 |
C4—H4A | 0.9700 | C18—C19 | 1.441 (2) |
C4—H4B | 0.9700 | C18—C20 | 1.495 (2) |
C5—C6 | 1.498 (2) | C21—C22 | 1.415 (5) |
C5—H5A | 0.9700 | C21—H21A | 0.9700 |
C5—H5B | 0.9700 | C21—H21B | 0.9700 |
C6—C18 | 1.351 (2) | C22—H22A | 0.9600 |
C7—C11 | 1.5158 (18) | C22—H22B | 0.9600 |
C7—C8 | 1.556 (2) | C22—H22C | 0.9600 |
C7—H7 | 0.9800 | ||
C20—O2—C21 | 117.29 (18) | N2—C9—C8 | 177.5 (3) |
C6—C1—C7 | 112.65 (11) | N1—C10—C8 | 178.2 (2) |
C6—C1—C2 | 107.22 (13) | C16—C11—C12 | 117.76 (14) |
C7—C1—C2 | 110.65 (13) | C16—C11—C7 | 119.73 (14) |
C6—C1—H1 | 108.7 | C12—C11—C7 | 122.51 (14) |
C7—C1—H1 | 108.7 | C11—C12—C13 | 120.84 (17) |
C2—C1—H1 | 108.7 | C11—C12—H12 | 119.6 |
C3—C2—C1 | 113.00 (15) | C13—C12—H12 | 119.6 |
C3—C2—H2A | 109.0 | C14—C13—C12 | 121.55 (18) |
C1—C2—H2A | 109.0 | C14—C13—H13 | 119.2 |
C3—C2—H2B | 109.0 | C12—C13—H13 | 119.2 |
C1—C2—H2B | 109.0 | C13—C14—C15 | 117.60 (15) |
H2A—C2—H2B | 107.8 | C13—C14—C17 | 120.90 (19) |
C4—C3—C2 | 111.15 (17) | C15—C14—C17 | 121.50 (19) |
C4—C3—H3A | 109.4 | C14—C15—C16 | 121.44 (17) |
C2—C3—H3A | 109.4 | C14—C15—H15 | 119.3 |
C4—C3—H3B | 109.4 | C16—C15—H15 | 119.3 |
C2—C3—H3B | 109.4 | C11—C16—C15 | 120.78 (16) |
H3A—C3—H3B | 108.0 | C11—C16—H16 | 119.6 |
C3—C4—C5 | 111.29 (15) | C15—C16—H16 | 119.6 |
C3—C4—H4A | 109.4 | C14—C17—H17A | 109.5 |
C5—C4—H4A | 109.4 | C14—C17—H17B | 109.5 |
C3—C4—H4B | 109.4 | H17A—C17—H17B | 109.5 |
C5—C4—H4B | 109.4 | C14—C17—H17C | 109.5 |
H4A—C4—H4B | 108.0 | H17A—C17—H17C | 109.5 |
C6—C5—C4 | 110.22 (15) | H17B—C17—H17C | 109.5 |
C6—C5—H5A | 109.6 | C6—C18—C19 | 119.19 (14) |
C4—C5—H5A | 109.6 | C6—C18—C20 | 126.34 (13) |
C6—C5—H5B | 109.6 | C19—C18—C20 | 114.46 (13) |
C4—C5—H5B | 109.6 | N3—C19—C18 | 177.98 (17) |
H5A—C5—H5B | 108.1 | O1—C20—O2 | 124.07 (18) |
C18—C6—C5 | 121.57 (13) | O1—C20—C18 | 125.98 (17) |
C18—C6—C1 | 123.37 (14) | O2—C20—C18 | 109.94 (15) |
C5—C6—C1 | 114.98 (12) | C22—C21—O2 | 109.9 (3) |
C11—C7—C1 | 111.82 (11) | C22—C21—H21A | 109.7 |
C11—C7—C8 | 112.83 (12) | O2—C21—H21A | 109.7 |
C1—C7—C8 | 111.14 (12) | C22—C21—H21B | 109.7 |
C11—C7—H7 | 106.9 | O2—C21—H21B | 109.7 |
C1—C7—H7 | 106.9 | H21A—C21—H21B | 108.2 |
C8—C7—H7 | 106.9 | C21—C22—H22A | 109.5 |
C10—C8—C9 | 108.96 (15) | C21—C22—H22B | 109.5 |
C10—C8—C7 | 111.69 (14) | H22A—C22—H22B | 109.5 |
C9—C8—C7 | 114.82 (14) | C21—C22—H22C | 109.5 |
C10—C8—H8 | 107.0 | H22A—C22—H22C | 109.5 |
C9—C8—H8 | 107.0 | H22B—C22—H22C | 109.5 |
C7—C8—H8 | 107.0 | ||
C6—C1—C2—C3 | 54.57 (19) | C8—C7—C11—C12 | 74.0 (2) |
C7—C1—C2—C3 | −68.63 (18) | C16—C11—C12—C13 | −1.4 (3) |
C1—C2—C3—C4 | −56.0 (2) | C7—C11—C12—C13 | 178.39 (17) |
C2—C3—C4—C5 | 54.3 (2) | C11—C12—C13—C14 | −0.1 (3) |
C3—C4—C5—C6 | −53.9 (2) | C12—C13—C14—C15 | 1.3 (3) |
C4—C5—C6—C18 | −120.06 (16) | C12—C13—C14—C17 | −178.9 (2) |
C4—C5—C6—C1 | 56.71 (17) | C13—C14—C15—C16 | −0.9 (3) |
C7—C1—C6—C18 | −117.15 (16) | C17—C14—C15—C16 | 179.3 (2) |
C2—C1—C6—C18 | 120.89 (16) | C12—C11—C16—C15 | 1.8 (3) |
C7—C1—C6—C5 | 66.15 (17) | C7—C11—C16—C15 | −178.03 (16) |
C2—C1—C6—C5 | −55.82 (17) | C14—C15—C16—C11 | −0.6 (3) |
C6—C1—C7—C11 | 178.52 (12) | C5—C6—C18—C19 | −0.8 (2) |
C2—C1—C7—C11 | −61.47 (17) | C1—C6—C18—C19 | −177.25 (13) |
C6—C1—C7—C8 | 51.44 (17) | C5—C6—C18—C20 | −179.74 (15) |
C2—C1—C7—C8 | 171.45 (13) | C1—C6—C18—C20 | 3.8 (2) |
C11—C7—C8—C10 | 57.22 (18) | C21—O2—C20—O1 | −0.9 (3) |
C1—C7—C8—C10 | −176.25 (13) | C21—O2—C20—C18 | 177.7 (2) |
C11—C7—C8—C9 | −67.48 (17) | C6—C18—C20—O1 | −28.4 (3) |
C1—C7—C8—C9 | 59.05 (17) | C19—C18—C20—O1 | 152.57 (19) |
C1—C7—C11—C16 | 127.58 (17) | C6—C18—C20—O2 | 153.07 (17) |
C8—C7—C11—C16 | −106.25 (18) | C19—C18—C20—O2 | −26.0 (2) |
C1—C7—C11—C12 | −52.2 (2) | C20—O2—C21—C22 | −169.7 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1···O1 | 0.98 | 2.23 | 3.001 (2) | 135 |
C5—H5A···N1i | 0.97 | 2.57 | 3.536 (3) | 172 |
C8—H8···N3ii | 0.98 | 2.27 | 3.221 (2) | 163 |
Symmetry codes: (i) −x, −y+2, −z+1; (ii) −x, −y+1, −z+1. |
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