organic compounds
(Z)-1-Diphenylmethyl-4-(3-phenylprop-2-enyl)piperazine
aVittal Mallya Scientific Research Foundation, #94/3, 23rd Cross, 29th Main, BTM II Stage, Bangalore 560 076, India, and bDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA
*Correspondence e-mail: jjasinski@keene.edu
In the title compound, C26H28N2, the piperazine group adopts a chair conformation with the exocyclic N—C bonds in equatorial orientations. The dihedral angle between the geminal benzene rings is 80.46 (12)° and the C=C—C—N torsion angle is 145.9 (2)°. In the crystal, weak C—H⋯π interactions link the molecules into [100] chains.
CCDC reference: 997025
Related literature
For the use of cinnerizine as an antihistamine, see: Paton & Webster (1985). For synthetic methods of (E)-isomers of 1-benzhydryl-4-cinnamyl piperazines, see: Cignarella & Testa (1968). For the synthesis of the Z-isomer of cinnerizine, see: Shivaprakash & Chandrasekara Reddy (2014).
Experimental
Crystal data
|
|
Data collection: CrysAlis PRO (Agilent, 2012); cell CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007; Palatinus & van der Lee, 2008; Palatinus et al., 2012); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2.
Supporting information
CCDC reference: 997025
10.1107/S1600536814008289/hb7219sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814008289/hb7219Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814008289/hb7219Isup3.cml
To a solution of 1-benzhydryl-4-(2-acetaldehyde) piperazine (5.0 g, 17.0 mmol) in dichloromethane (50 ml) under N2 atmosphere was added benzyltriphenyl phosphonium chloride (6.9 g, 17.9 mmol). The mixture was cooled to 278°K and t-BuOK (4.6 g, 41.3 mmol) was added under stirring. After completion, the reaction mass was quenched into water (100 ml). The organic layer was separated, dried over anhydrous sodium sulphate and concentrated under vacuum which was then subjected to
over silica gel with a EtOAc/Hexane mixture to afford the pure form of (Z)-1-benzhydrl-4-cinnamylpiperazine which was crystallized using absolute ethanol, white solid, mp: 363-365 K.All of the H atoms were placed in their calculated positions and then refined using the riding model with Atom—H lengths of 0.95Å (CH) or 0.99Å (CH2). Isotropic displacement parameters for these atoms were set to 1.2 (CH, CH2)times Ueq of the parent atom.
Data collection: CrysAlis PRO (Agilent, 2012); cell
CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis RED (Agilent, 2012); program(s) used to solve structure: Superflip (Palatinus & Chapuis, 2007; Palatinus & van der Lee, 2008; Palatinus et al., 2012); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).Fig. 1. ORTEP drawing of (I), C26H28N2, showing 30% probability displacement ellipsoids. |
C26H28N2 | F(000) = 396 |
Mr = 368.50 | Dx = 1.166 Mg m−3 |
Monoclinic, Pn | Cu Kα radiation, λ = 1.54184 Å |
a = 8.7823 (3) Å | Cell parameters from 3666 reflections |
b = 9.6068 (3) Å | θ = 3.6–71.1° |
c = 12.4894 (4) Å | µ = 0.52 mm−1 |
β = 94.834 (3)° | T = 173 K |
V = 1049.97 (6) Å3 | Irregular, colourless |
Z = 2 | 0.42 × 0.38 × 0.32 mm |
Agilent Eos Gemini diffractometer | 3316 independent reflections |
Radiation source: Enhance (Cu) X-ray Source | 3177 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
Detector resolution: 16.0416 pixels mm-1 | θmax = 71.0°, θmin = 4.6° |
ω scans | h = −10→9 |
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012) | k = −11→9 |
Tmin = 0.907, Tmax = 1.000 | l = −15→14 |
6399 measured reflections |
Refinement on F2 | H-atom parameters constrained |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.0592P)2 + 0.0586P] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.035 | (Δ/σ)max < 0.001 |
wR(F2) = 0.096 | Δρmax = 0.13 e Å−3 |
S = 1.05 | Δρmin = −0.14 e Å−3 |
3316 reflections | Extinction correction: SHELXL2012 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
254 parameters | Extinction coefficient: 0.0072 (12) |
2 restraints | Absolute structure: Flack parameter determined using 1186 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.1 (4) |
Hydrogen site location: inferred from neighbouring sites |
C26H28N2 | V = 1049.97 (6) Å3 |
Mr = 368.50 | Z = 2 |
Monoclinic, Pn | Cu Kα radiation |
a = 8.7823 (3) Å | µ = 0.52 mm−1 |
b = 9.6068 (3) Å | T = 173 K |
c = 12.4894 (4) Å | 0.42 × 0.38 × 0.32 mm |
β = 94.834 (3)° |
Agilent Eos Gemini diffractometer | 3316 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012) | 3177 reflections with I > 2σ(I) |
Tmin = 0.907, Tmax = 1.000 | Rint = 0.027 |
6399 measured reflections |
R[F2 > 2σ(F2)] = 0.035 | H-atom parameters constrained |
wR(F2) = 0.096 | Δρmax = 0.13 e Å−3 |
S = 1.05 | Δρmin = −0.14 e Å−3 |
3316 reflections | Absolute structure: Flack parameter determined using 1186 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
254 parameters | Absolute structure parameter: 0.1 (4) |
2 restraints |
Experimental. 1H NMR: δ 7.10 - 7.42 (m, 15 H, Ar-H), 6.55 (d, J =12.0 Hz, 1 H), 5.77 (ddd, J =12.0, 6.6 Hz, 1 H), 4.22 (s, 1 H), 3.28 (dd, J = 6.6, 1.80 Hz, 2 H), 2.46 (bs, 8 H). 13C NMR: δ 142.8, 137.1, 131.6, 129.5, 128.9, 128.4, 128.1, 127.9, 126.9, 126.8, 76.2, 56.2, 53.5, 51.9. HRMS calculated for C26H28N2 [M+H] + 369.2331; found 369.2335. |
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. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.5869 (2) | 0.85143 (18) | 0.65925 (14) | 0.0334 (4) | |
N2 | 0.72189 (19) | 0.64457 (18) | 0.80568 (14) | 0.0305 (4) | |
C1 | 0.7507 (2) | 0.8187 (2) | 0.66743 (17) | 0.0328 (5) | |
H1A | 0.8089 | 0.9024 | 0.6492 | 0.039* | |
H1B | 0.7703 | 0.7447 | 0.6152 | 0.039* | |
C2 | 0.8049 (2) | 0.7707 (2) | 0.77981 (17) | 0.0340 (5) | |
H2A | 0.9159 | 0.7512 | 0.7841 | 0.041* | |
H2B | 0.7867 | 0.8448 | 0.8323 | 0.041* | |
C3 | 0.5597 (3) | 0.6811 (2) | 0.80277 (18) | 0.0359 (5) | |
H3A | 0.5452 | 0.7557 | 0.8556 | 0.043* | |
H3B | 0.5001 | 0.5988 | 0.8225 | 0.043* | |
C4 | 0.5024 (2) | 0.7302 (2) | 0.69132 (17) | 0.0344 (5) | |
H4A | 0.5132 | 0.6539 | 0.6392 | 0.041* | |
H4B | 0.3925 | 0.7539 | 0.6903 | 0.041* | |
C5 | 0.5349 (3) | 0.8889 (2) | 0.54764 (18) | 0.0377 (5) | |
H5A | 0.4226 | 0.9018 | 0.5414 | 0.045* | |
H5B | 0.5592 | 0.8123 | 0.4990 | 0.045* | |
C6 | 0.6101 (3) | 1.0202 (2) | 0.5143 (2) | 0.0442 (6) | |
H6 | 0.6307 | 1.0881 | 0.5689 | 0.053* | |
C7 | 0.6514 (3) | 1.0529 (2) | 0.4176 (2) | 0.0459 (6) | |
H7 | 0.7040 | 1.1386 | 0.4117 | 0.055* | |
C8 | 0.6241 (3) | 0.9702 (2) | 0.31837 (19) | 0.0385 (5) | |
C9 | 0.4864 (3) | 0.9022 (2) | 0.29280 (18) | 0.0377 (5) | |
H9 | 0.4093 | 0.9051 | 0.3418 | 0.045* | |
C10 | 0.4595 (3) | 0.8300 (2) | 0.19678 (19) | 0.0448 (6) | |
H10 | 0.3638 | 0.7852 | 0.1806 | 0.054* | |
C11 | 0.5692 (4) | 0.8225 (3) | 0.1250 (2) | 0.0551 (7) | |
H11 | 0.5501 | 0.7723 | 0.0598 | 0.066* | |
C12 | 0.7067 (4) | 0.8881 (3) | 0.1485 (2) | 0.0614 (8) | |
H12 | 0.7835 | 0.8824 | 0.0994 | 0.074* | |
C13 | 0.7345 (3) | 0.9627 (3) | 0.2430 (2) | 0.0522 (7) | |
H13 | 0.8294 | 1.0095 | 0.2572 | 0.063* | |
C14 | 0.7777 (2) | 0.5848 (2) | 0.91021 (16) | 0.0321 (5) | |
H14 | 0.7564 | 0.6523 | 0.9681 | 0.039* | |
C15 | 0.6962 (2) | 0.4481 (2) | 0.93040 (19) | 0.0370 (5) | |
C16 | 0.6542 (3) | 0.3558 (3) | 0.8466 (2) | 0.0465 (6) | |
H16 | 0.6703 | 0.3810 | 0.7749 | 0.056* | |
C17 | 0.5894 (3) | 0.2279 (3) | 0.8667 (3) | 0.0617 (8) | |
H17 | 0.5625 | 0.1659 | 0.8089 | 0.074* | |
C18 | 0.5639 (3) | 0.1902 (3) | 0.9704 (3) | 0.0702 (10) | |
H18 | 0.5183 | 0.1031 | 0.9842 | 0.084* | |
C19 | 0.6051 (3) | 0.2801 (4) | 1.0533 (3) | 0.0696 (10) | |
H19 | 0.5892 | 0.2539 | 1.1249 | 0.083* | |
C20 | 0.6700 (3) | 0.4093 (3) | 1.0340 (2) | 0.0496 (6) | |
H20 | 0.6962 | 0.4708 | 1.0921 | 0.060* | |
C21 | 0.9488 (2) | 0.5561 (2) | 0.91718 (17) | 0.0304 (4) | |
C22 | 1.0405 (3) | 0.5915 (2) | 1.00883 (18) | 0.0364 (5) | |
H22 | 0.9979 | 0.6412 | 1.0649 | 0.044* | |
C23 | 1.1937 (3) | 0.5551 (3) | 1.0193 (2) | 0.0433 (6) | |
H23 | 1.2553 | 0.5794 | 1.0828 | 0.052* | |
C24 | 1.2572 (3) | 0.4838 (2) | 0.9382 (2) | 0.0416 (6) | |
H24 | 1.3622 | 0.4585 | 0.9457 | 0.050* | |
C25 | 1.1672 (3) | 0.4492 (3) | 0.8459 (2) | 0.0433 (5) | |
H25 | 1.2102 | 0.4001 | 0.7898 | 0.052* | |
C26 | 1.0146 (3) | 0.4860 (2) | 0.83531 (19) | 0.0389 (5) | |
H26 | 0.9538 | 0.4631 | 0.7712 | 0.047* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0309 (10) | 0.0336 (8) | 0.0341 (9) | 0.0054 (7) | −0.0063 (7) | −0.0034 (7) |
N2 | 0.0229 (9) | 0.0342 (8) | 0.0337 (9) | 0.0008 (7) | −0.0025 (7) | 0.0018 (7) |
C1 | 0.0289 (11) | 0.0311 (10) | 0.0377 (11) | 0.0010 (8) | −0.0015 (9) | 0.0001 (8) |
C2 | 0.0263 (11) | 0.0351 (10) | 0.0392 (11) | −0.0010 (8) | −0.0061 (8) | −0.0001 (9) |
C3 | 0.0265 (11) | 0.0424 (11) | 0.0388 (11) | 0.0038 (8) | 0.0015 (9) | 0.0017 (9) |
C4 | 0.0242 (10) | 0.0393 (10) | 0.0386 (12) | 0.0050 (8) | −0.0039 (8) | −0.0047 (9) |
C5 | 0.0372 (13) | 0.0371 (11) | 0.0367 (12) | 0.0065 (9) | −0.0089 (9) | −0.0044 (8) |
C6 | 0.0520 (16) | 0.0312 (10) | 0.0456 (13) | 0.0043 (10) | −0.0184 (11) | −0.0026 (9) |
C7 | 0.0510 (16) | 0.0298 (10) | 0.0540 (15) | −0.0028 (10) | −0.0134 (12) | 0.0067 (9) |
C8 | 0.0442 (14) | 0.0277 (9) | 0.0427 (12) | 0.0041 (9) | −0.0026 (10) | 0.0105 (8) |
C9 | 0.0391 (13) | 0.0358 (11) | 0.0376 (11) | 0.0072 (9) | −0.0007 (9) | 0.0030 (9) |
C10 | 0.0541 (16) | 0.0383 (11) | 0.0403 (12) | 0.0057 (10) | −0.0061 (11) | 0.0019 (9) |
C11 | 0.081 (2) | 0.0448 (13) | 0.0399 (14) | 0.0096 (13) | 0.0088 (13) | 0.0032 (10) |
C12 | 0.081 (2) | 0.0510 (14) | 0.0570 (16) | 0.0110 (15) | 0.0313 (16) | 0.0143 (13) |
C13 | 0.0481 (16) | 0.0423 (12) | 0.0671 (17) | −0.0029 (11) | 0.0097 (12) | 0.0179 (12) |
C14 | 0.0285 (11) | 0.0376 (10) | 0.0298 (10) | 0.0043 (9) | −0.0007 (8) | −0.0001 (8) |
C15 | 0.0217 (10) | 0.0467 (12) | 0.0428 (12) | 0.0061 (8) | 0.0044 (9) | 0.0095 (9) |
C16 | 0.0382 (14) | 0.0439 (12) | 0.0590 (15) | −0.0051 (10) | 0.0139 (11) | 0.0017 (11) |
C17 | 0.0424 (16) | 0.0480 (14) | 0.096 (2) | −0.0056 (12) | 0.0120 (15) | 0.0047 (14) |
C18 | 0.0332 (14) | 0.0609 (17) | 0.116 (3) | −0.0057 (13) | 0.0018 (16) | 0.042 (2) |
C19 | 0.0252 (13) | 0.106 (3) | 0.077 (2) | 0.0017 (14) | 0.0016 (12) | 0.057 (2) |
C20 | 0.0233 (12) | 0.0780 (17) | 0.0469 (14) | 0.0040 (11) | −0.0009 (10) | 0.0215 (13) |
C21 | 0.0273 (11) | 0.0285 (9) | 0.0345 (10) | −0.0011 (7) | −0.0016 (8) | 0.0052 (8) |
C22 | 0.0364 (12) | 0.0367 (10) | 0.0349 (11) | −0.0057 (9) | −0.0034 (9) | 0.0027 (9) |
C23 | 0.0337 (12) | 0.0505 (12) | 0.0429 (13) | −0.0116 (10) | −0.0136 (10) | 0.0092 (10) |
C24 | 0.0233 (11) | 0.0470 (12) | 0.0533 (14) | −0.0029 (9) | −0.0032 (10) | 0.0184 (10) |
C25 | 0.0317 (12) | 0.0492 (13) | 0.0493 (13) | 0.0060 (9) | 0.0043 (10) | 0.0017 (10) |
C26 | 0.0287 (12) | 0.0482 (12) | 0.0385 (11) | 0.0041 (9) | −0.0047 (9) | −0.0049 (9) |
N1—C1 | 1.467 (3) | C11—C12 | 1.372 (5) |
N1—C4 | 1.456 (3) | C12—H12 | 0.9500 |
N1—C5 | 1.475 (3) | C12—C13 | 1.385 (4) |
N2—C2 | 1.464 (3) | C13—H13 | 0.9500 |
N2—C3 | 1.465 (3) | C14—H14 | 1.0000 |
N2—C14 | 1.472 (3) | C14—C15 | 1.527 (3) |
C1—H1A | 0.9900 | C14—C21 | 1.523 (3) |
C1—H1B | 0.9900 | C15—C16 | 1.397 (4) |
C1—C2 | 1.516 (3) | C15—C20 | 1.384 (3) |
C2—H2A | 0.9900 | C16—H16 | 0.9500 |
C2—H2B | 0.9900 | C16—C17 | 1.386 (4) |
C3—H3A | 0.9900 | C17—H17 | 0.9500 |
C3—H3B | 0.9900 | C17—C18 | 1.381 (5) |
C3—C4 | 1.515 (3) | C18—H18 | 0.9500 |
C4—H4A | 0.9900 | C18—C19 | 1.373 (6) |
C4—H4B | 0.9900 | C19—H19 | 0.9500 |
C5—H5A | 0.9900 | C19—C20 | 1.395 (5) |
C5—H5B | 0.9900 | C20—H20 | 0.9500 |
C5—C6 | 1.499 (3) | C21—C22 | 1.385 (3) |
C6—H6 | 0.9500 | C21—C26 | 1.390 (3) |
C6—C7 | 1.328 (4) | C22—H22 | 0.9500 |
C7—H7 | 0.9500 | C22—C23 | 1.386 (3) |
C7—C8 | 1.475 (3) | C23—H23 | 0.9500 |
C8—C9 | 1.388 (3) | C23—C24 | 1.380 (4) |
C8—C13 | 1.409 (4) | C24—H24 | 0.9500 |
C9—H9 | 0.9500 | C24—C25 | 1.382 (4) |
C9—C10 | 1.388 (3) | C25—H25 | 0.9500 |
C10—H10 | 0.9500 | C25—C26 | 1.381 (3) |
C10—C11 | 1.372 (4) | C26—H26 | 0.9500 |
C11—H11 | 0.9500 | ||
C1—N1—C5 | 110.01 (17) | C10—C11—H11 | 120.3 |
C4—N1—C1 | 109.22 (16) | C10—C11—C12 | 119.4 (3) |
C4—N1—C5 | 109.34 (17) | C12—C11—H11 | 120.3 |
C2—N2—C3 | 107.32 (16) | C11—C12—H12 | 119.7 |
C2—N2—C14 | 112.58 (16) | C11—C12—C13 | 120.6 (3) |
C3—N2—C14 | 111.44 (17) | C13—C12—H12 | 119.7 |
N1—C1—H1A | 109.4 | C8—C13—H13 | 119.5 |
N1—C1—H1B | 109.4 | C12—C13—C8 | 120.9 (3) |
N1—C1—C2 | 111.06 (18) | C12—C13—H13 | 119.5 |
H1A—C1—H1B | 108.0 | N2—C14—H14 | 108.6 |
C2—C1—H1A | 109.4 | N2—C14—C15 | 110.89 (17) |
C2—C1—H1B | 109.4 | N2—C14—C21 | 111.98 (17) |
N2—C2—C1 | 109.45 (17) | C15—C14—H14 | 108.6 |
N2—C2—H2A | 109.8 | C21—C14—H14 | 108.6 |
N2—C2—H2B | 109.8 | C21—C14—C15 | 107.97 (17) |
C1—C2—H2A | 109.8 | C16—C15—C14 | 121.3 (2) |
C1—C2—H2B | 109.8 | C20—C15—C14 | 120.2 (2) |
H2A—C2—H2B | 108.2 | C20—C15—C16 | 118.3 (2) |
N2—C3—H3A | 109.6 | C15—C16—H16 | 119.5 |
N2—C3—H3B | 109.6 | C17—C16—C15 | 120.9 (3) |
N2—C3—C4 | 110.14 (18) | C17—C16—H16 | 119.5 |
H3A—C3—H3B | 108.1 | C16—C17—H17 | 119.9 |
C4—C3—H3A | 109.6 | C18—C17—C16 | 120.2 (3) |
C4—C3—H3B | 109.6 | C18—C17—H17 | 119.9 |
N1—C4—C3 | 111.38 (18) | C17—C18—H18 | 120.3 |
N1—C4—H4A | 109.4 | C19—C18—C17 | 119.3 (3) |
N1—C4—H4B | 109.4 | C19—C18—H18 | 120.3 |
C3—C4—H4A | 109.4 | C18—C19—H19 | 119.5 |
C3—C4—H4B | 109.4 | C18—C19—C20 | 120.9 (3) |
H4A—C4—H4B | 108.0 | C20—C19—H19 | 119.5 |
N1—C5—H5A | 109.4 | C15—C20—C19 | 120.3 (3) |
N1—C5—H5B | 109.4 | C15—C20—H20 | 119.9 |
N1—C5—C6 | 111.06 (18) | C19—C20—H20 | 119.9 |
H5A—C5—H5B | 108.0 | C22—C21—C14 | 120.31 (19) |
C6—C5—H5A | 109.4 | C22—C21—C26 | 118.6 (2) |
C6—C5—H5B | 109.4 | C26—C21—C14 | 121.00 (19) |
C5—C6—H6 | 116.1 | C21—C22—H22 | 119.7 |
C7—C6—C5 | 127.8 (2) | C21—C22—C23 | 120.6 (2) |
C7—C6—H6 | 116.1 | C23—C22—H22 | 119.7 |
C6—C7—H7 | 116.6 | C22—C23—H23 | 119.8 |
C6—C7—C8 | 126.8 (2) | C24—C23—C22 | 120.3 (2) |
C8—C7—H7 | 116.6 | C24—C23—H23 | 119.8 |
C9—C8—C7 | 121.6 (2) | C23—C24—H24 | 120.2 |
C9—C8—C13 | 117.2 (2) | C23—C24—C25 | 119.6 (2) |
C13—C8—C7 | 121.1 (2) | C25—C24—H24 | 120.2 |
C8—C9—H9 | 119.5 | C24—C25—H25 | 120.0 |
C10—C9—C8 | 121.0 (2) | C26—C25—C24 | 120.1 (2) |
C10—C9—H9 | 119.5 | C26—C25—H25 | 120.0 |
C9—C10—H10 | 119.6 | C21—C26—H26 | 119.6 |
C11—C10—C9 | 120.8 (3) | C25—C26—C21 | 120.9 (2) |
C11—C10—H10 | 119.6 | C25—C26—H26 | 119.6 |
N1—C1—C2—N2 | 60.7 (2) | C9—C10—C11—C12 | −0.5 (4) |
N1—C5—C6—C7 | 145.9 (2) | C10—C11—C12—C13 | −0.7 (4) |
N2—C3—C4—N1 | −59.4 (2) | C11—C12—C13—C8 | 1.5 (4) |
N2—C14—C15—C16 | 35.6 (3) | C13—C8—C9—C10 | 0.0 (3) |
N2—C14—C15—C20 | −148.1 (2) | C14—N2—C2—C1 | 175.11 (17) |
N2—C14—C21—C22 | 135.90 (19) | C14—N2—C3—C4 | −174.99 (17) |
N2—C14—C21—C26 | −48.3 (3) | C14—C15—C16—C17 | 175.7 (2) |
C1—N1—C4—C3 | 55.5 (2) | C14—C15—C20—C19 | −175.6 (2) |
C1—N1—C5—C6 | −64.6 (2) | C14—C21—C22—C23 | 174.5 (2) |
C2—N2—C3—C4 | 61.3 (2) | C14—C21—C26—C25 | −174.2 (2) |
C2—N2—C14—C15 | −175.90 (17) | C15—C14—C21—C22 | −101.7 (2) |
C2—N2—C14—C21 | −55.2 (2) | C15—C14—C21—C26 | 74.0 (3) |
C3—N2—C2—C1 | −61.9 (2) | C15—C16—C17—C18 | 0.7 (4) |
C3—N2—C14—C15 | 63.4 (2) | C16—C15—C20—C19 | 0.9 (3) |
C3—N2—C14—C21 | −175.87 (17) | C16—C17—C18—C19 | −0.8 (5) |
C4—N1—C1—C2 | −56.3 (2) | C17—C18—C19—C20 | 1.0 (4) |
C4—N1—C5—C6 | 175.45 (19) | C18—C19—C20—C15 | −1.1 (4) |
C5—N1—C1—C2 | −176.29 (16) | C20—C15—C16—C17 | −0.7 (4) |
C5—N1—C4—C3 | 175.89 (17) | C21—C14—C15—C16 | −87.5 (2) |
C5—C6—C7—C8 | 4.0 (4) | C21—C14—C15—C20 | 88.9 (2) |
C6—C7—C8—C9 | 40.9 (4) | C21—C22—C23—C24 | 0.4 (3) |
C6—C7—C8—C13 | −142.3 (3) | C22—C21—C26—C25 | 1.6 (3) |
C7—C8—C9—C10 | 177.0 (2) | C22—C23—C24—C25 | 0.3 (3) |
C7—C8—C13—C12 | −178.2 (2) | C23—C24—C25—C26 | 0.0 (3) |
C8—C9—C10—C11 | 0.8 (3) | C24—C25—C26—C21 | −0.9 (4) |
C9—C8—C13—C12 | −1.2 (3) | C26—C21—C22—C23 | −1.4 (3) |
Cg1 is the centroid of the C15–C20 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C24—H24···Cg1i | 0.95 | 2.70 | 3.629 (3) | 164 |
Symmetry code: (i) x+1, y, z. |
Cg1 is the centroid of the C15–C20 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C24—H24···Cg1i | 0.95 | 2.70 | 3.629 (3) | 164 |
Symmetry code: (i) x+1, y, z. |
Acknowledgements
We express our sincere thanks to Dr Anil Kush, Director, VMSRF, for his keen interest and support throughout this work. JPJ acknowledges the NSF–MRI program (grant No. CHE-1039027) for funds to purchase the X-ray diffractometer.
References
Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England. Google Scholar
Cignarella, G. & Testa, E. V. J. (1968). Med. Chem. 11, 612–615. CrossRef CAS Web of Science Google Scholar
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341. Web of Science CrossRef CAS IUCr Journals Google Scholar
Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786–790. Web of Science CrossRef CAS IUCr Journals Google Scholar
Palatinus, L., Prathapa, S. J. & van Smaalen, S. (2012). J. Appl. Cryst. 45, 575–580. Web of Science CrossRef CAS IUCr Journals Google Scholar
Palatinus, L. & van der Lee, A. (2008). J. Appl. Cryst. 41, 975–984. Web of Science CrossRef CAS IUCr Journals Google Scholar
Parsons, S., Flack, H. D. & Wagner, T. (2013). Acta Cryst. B69, 249–259. Web of Science CrossRef CAS IUCr Journals Google Scholar
Paton, D. M. & Webster, D. R. (1985). Clin. Pharmacokinet., 10, 477–497. CrossRef CAS PubMed Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shivaprakash, S. & Chandrasekara Reddy, G. (2014). Synth. Commun. 44, 600–609. Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Cinnerizine: (E)-1-(Diphenyl)methyl)-4-(3-phenyl-2-propenyl)piperazine is marketed as stugeron which is used as antihistamine (Paton & Webster, 1985). Because of greater biological importance of (E)-isomers of 1-benzhydryl-4-cinnamyl piperazines, several synthetic methods are described (Cignarella & Testa, 1968). But only recently the synthesis of (Z)-1-(Diphenylmethyl)-4-(3-phenyl-2-propenyl)piperazine is reported (Shivaprakash & Chandrasekara Reddy, 2014).
The title compound, C26H28N2, (I), is a close analogue of an existing drug viz., Cinnarizine, which has (E) geometry. We have prepared for the first time the (Z) isomer to study the structure activity relationship. However there is no report of any crystallographic data for this molecule so far. Hence this study was performed to confirm its structure. This compound exists as solid in free base form which could be crystallized easily. In continuation of our work in this area, we report here the crystal structure of (I).
In (I), the piperazine group adopts a slightly distorted chair conformation (puckering parameters Q, θ, and ϕ = 0.597 (2)Å, 3.95 (19)° and 168 (3)°, respectively (Fig. 1). The dihedral angles between the mean planes of the two methyl diphenyl groups (C15–C20 and C21–C26) with that of the 2-propenyl phenyl group (C8–C13) are 35.2 (1)° and 45.8 (8)°, respectively. The two methyl phenyl groups are separated by 80.4 (6)° with respect to each other.