organic compounds
1-Piperonylpiperazinium 4-chlorobenzoate
aDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, 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 salt {systematic name: 1-[(1,3-benzodioxol-5-yl)methyl]piperazin-1-ium 4-chlorobenzoate}, C12H17N2O2+·C7H4ClO2−, the piperazine ring adopts a slightly disordered chair conformation. The dioxole ring is in a flattened with the methylene C atom forming the flap. The relative orientation of the piperonyl ring system and the piperazine rings is reflected in the N—C—C C torsion angle of 132.3 (1)°. In the anion, the mean plane of the carboxylate group is twisted from that of the benzene ring by 14.8 (9)°. In the crystal, the components are linked by N—H⋯O and weak C—H⋯O hydrogen bonds, forming chains along [010].
CCDC reference: 984052
Related literature
For the biological activity of related compounds, see: Brockunier et al. (2004); Bogatcheva et al. (2006); Elliott (2011); Gilbert et al. (1968); Gobert et al. (2003); Millan et al. (2001). For a related structure, see: Capuano et al. (2000). For puckering parameters, see: Cremer & Pople (1975). For standard bond lengths, see: Allen et al. (1987).
Experimental
Crystal data
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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); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008) in OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).
Supporting information
CCDC reference: 984052
10.1107/S1600536814002037/lh5687sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814002037/lh5687Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814002037/lh5687Isup3.cml
1-piperonylpiperazine ( 2.2 g, 0.01 mol) and p-chlorobenzoic acid (1.56 g, 0.01 mol) were dissolved in hot N,N-dimethylformamide and stirred for 10 mins at 323 K. The resulting solution was allowed to cool slowly at room temperature. The crystals of the title salt appeared after a few days and were suitable for X-ray studies (m.p.:464-470 K).
All H atoms were placed in calculated positions and then refined using the riding-model approximation with Atom—H lengths of 0.93Å (CH), 0.97Å (CH2) or 0.90Å (NH). Isotropic displacement parameters were set to 1.2Ueq 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); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008) in OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).Fig. 1. The asymmetric unit of (I) with 30% probability displacement ellipsoids. | |
Fig. 2. Crystal packing of (I) viewed along the c axis. Dashed lines indicate N—H···O and weak C—H···O interactions forming infinite 1-D chains along the b axis. H atoms not involved in hydrogen bonding have been removed for clarity. |
C12H17N2O2+·C7H4ClO2− | F(000) = 792 |
Mr = 376.83 | Dx = 1.380 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 16.9967 (6) Å | Cell parameters from 5056 reflections |
b = 8.5990 (3) Å | θ = 3.1–32.8° |
c = 12.4150 (5) Å | µ = 0.24 mm−1 |
β = 90.923 (3)° | T = 173 K |
V = 1814.27 (12) Å3 | Irregular, light yellow |
Z = 4 | 0.48 × 0.26 × 0.18 mm |
Agilent Gemini EOS diffractometer | 6302 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 4472 reflections with I > 2σ(I) |
Detector resolution: 16.0416 pixels mm-1 | Rint = 0.033 |
ω scans | θmax = 32.8°, θmin = 3.1° |
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012) | h = −21→25 |
Tmin = 0.787, Tmax = 1.000 | k = −12→12 |
22917 measured reflections | l = −17→18 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.048 | H-atom parameters constrained |
wR(F2) = 0.120 | w = 1/[σ2(Fo2) + (0.0455P)2 + 0.5274P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
6302 reflections | Δρmax = 0.30 e Å−3 |
235 parameters | Δρmin = −0.32 e Å−3 |
0 restraints |
C12H17N2O2+·C7H4ClO2− | V = 1814.27 (12) Å3 |
Mr = 376.83 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 16.9967 (6) Å | µ = 0.24 mm−1 |
b = 8.5990 (3) Å | T = 173 K |
c = 12.4150 (5) Å | 0.48 × 0.26 × 0.18 mm |
β = 90.923 (3)° |
Agilent Gemini EOS diffractometer | 6302 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012) | 4472 reflections with I > 2σ(I) |
Tmin = 0.787, Tmax = 1.000 | Rint = 0.033 |
22917 measured reflections |
R[F2 > 2σ(F2)] = 0.048 | 0 restraints |
wR(F2) = 0.120 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.30 e Å−3 |
6302 reflections | Δρmin = −0.32 e Å−3 |
235 parameters |
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 | ||
O1A | 0.46343 (6) | 0.65641 (14) | 0.06488 (9) | 0.0439 (3) | |
O2A | 0.55838 (7) | 0.84302 (13) | 0.03707 (9) | 0.0452 (3) | |
N1A | 0.79257 (6) | 0.70236 (13) | 0.30762 (9) | 0.0280 (2) | |
N2A | 0.95243 (6) | 0.60800 (13) | 0.27472 (10) | 0.0298 (2) | |
H2AA | 0.9590 | 0.5293 | 0.3218 | 0.036* | |
H2AB | 0.9978 | 0.6209 | 0.2395 | 0.036* | |
C1A | 0.71612 (8) | 0.69075 (19) | 0.35969 (12) | 0.0360 (3) | |
H1AA | 0.7072 | 0.7843 | 0.4014 | 0.043* | |
H1AB | 0.7170 | 0.6033 | 0.4090 | 0.043* | |
C2A | 0.64927 (8) | 0.66996 (16) | 0.27979 (11) | 0.0301 (3) | |
C3A | 0.64318 (8) | 0.77080 (16) | 0.19132 (11) | 0.0321 (3) | |
H3A | 0.6810 | 0.8466 | 0.1789 | 0.039* | |
C4A | 0.57955 (8) | 0.75298 (16) | 0.12438 (11) | 0.0304 (3) | |
C5A | 0.49379 (11) | 0.7623 (2) | −0.01222 (14) | 0.0474 (4) | |
H5AA | 0.4533 | 0.8355 | −0.0346 | 0.057* | |
H5AB | 0.5113 | 0.7063 | −0.0753 | 0.057* | |
C6A | 0.52267 (8) | 0.64112 (17) | 0.14120 (11) | 0.0312 (3) | |
C7A | 0.52767 (9) | 0.54095 (18) | 0.22546 (12) | 0.0373 (3) | |
H7A | 0.4895 | 0.4654 | 0.2367 | 0.045* | |
C8A | 0.59275 (9) | 0.55669 (18) | 0.29434 (12) | 0.0352 (3) | |
H8A | 0.5983 | 0.4885 | 0.3521 | 0.042* | |
C9A | 0.85456 (8) | 0.73757 (16) | 0.38737 (11) | 0.0305 (3) | |
H9AA | 0.8570 | 0.6553 | 0.4408 | 0.037* | |
H9AB | 0.8422 | 0.8340 | 0.4239 | 0.037* | |
C10A | 0.93326 (8) | 0.75244 (15) | 0.33388 (12) | 0.0313 (3) | |
H10A | 0.9320 | 0.8395 | 0.2842 | 0.038* | |
H10B | 0.9738 | 0.7727 | 0.3880 | 0.038* | |
C11A | 0.88861 (8) | 0.56853 (18) | 0.19658 (12) | 0.0349 (3) | |
H11A | 0.9003 | 0.4701 | 0.1621 | 0.042* | |
H11B | 0.8854 | 0.6479 | 0.1412 | 0.042* | |
C12A | 0.81076 (8) | 0.55708 (16) | 0.25287 (12) | 0.0316 (3) | |
H12A | 0.7695 | 0.5336 | 0.2005 | 0.038* | |
H12B | 0.8129 | 0.4730 | 0.3049 | 0.038* | |
Cl1B | 0.33436 (2) | 0.68123 (5) | 0.27279 (3) | 0.04524 (12) | |
O1B | 0.02434 (6) | 0.65334 (11) | 0.59960 (8) | 0.0335 (2) | |
O2B | 0.07906 (6) | 0.87721 (13) | 0.65085 (9) | 0.0411 (3) | |
C1B | 0.14214 (7) | 0.73384 (14) | 0.51518 (10) | 0.0255 (2) | |
C2B | 0.21013 (8) | 0.82354 (16) | 0.52310 (12) | 0.0308 (3) | |
H2B | 0.2152 | 0.8966 | 0.5780 | 0.037* | |
C3B | 0.27034 (8) | 0.80532 (16) | 0.45013 (12) | 0.0339 (3) | |
H3B | 0.3161 | 0.8642 | 0.4562 | 0.041* | |
C4B | 0.26105 (8) | 0.69800 (16) | 0.36822 (11) | 0.0310 (3) | |
C5B | 0.19465 (8) | 0.60586 (16) | 0.35906 (11) | 0.0311 (3) | |
H5B | 0.1897 | 0.5333 | 0.3038 | 0.037* | |
C6B | 0.13543 (8) | 0.62363 (15) | 0.43395 (11) | 0.0284 (3) | |
H6B | 0.0909 | 0.5610 | 0.4296 | 0.034* | |
C7B | 0.07682 (8) | 0.75601 (15) | 0.59450 (11) | 0.0275 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1A | 0.0290 (5) | 0.0598 (7) | 0.0426 (6) | −0.0056 (5) | −0.0065 (4) | 0.0000 (5) |
O2A | 0.0446 (6) | 0.0445 (6) | 0.0461 (6) | −0.0058 (5) | −0.0140 (5) | 0.0112 (5) |
N1A | 0.0247 (5) | 0.0295 (5) | 0.0297 (6) | 0.0009 (4) | −0.0029 (4) | −0.0040 (4) |
N2A | 0.0248 (5) | 0.0248 (5) | 0.0398 (6) | 0.0004 (4) | −0.0013 (4) | 0.0035 (5) |
C1A | 0.0289 (7) | 0.0482 (9) | 0.0310 (7) | 0.0017 (6) | 0.0001 (5) | −0.0022 (6) |
C2A | 0.0243 (6) | 0.0350 (7) | 0.0311 (6) | 0.0031 (5) | 0.0028 (5) | −0.0031 (5) |
C3A | 0.0278 (6) | 0.0295 (7) | 0.0391 (7) | −0.0028 (5) | 0.0005 (5) | −0.0004 (5) |
C4A | 0.0292 (6) | 0.0292 (6) | 0.0328 (7) | 0.0029 (5) | 0.0012 (5) | −0.0007 (5) |
C5A | 0.0497 (10) | 0.0517 (10) | 0.0403 (8) | −0.0057 (8) | −0.0118 (7) | −0.0001 (7) |
C6A | 0.0226 (6) | 0.0374 (7) | 0.0337 (7) | 0.0002 (5) | 0.0022 (5) | −0.0067 (6) |
C7A | 0.0312 (7) | 0.0422 (8) | 0.0387 (8) | −0.0097 (6) | 0.0072 (6) | −0.0005 (6) |
C8A | 0.0341 (7) | 0.0399 (8) | 0.0317 (7) | −0.0015 (6) | 0.0058 (5) | 0.0035 (6) |
C9A | 0.0309 (7) | 0.0293 (6) | 0.0310 (6) | 0.0010 (5) | −0.0055 (5) | −0.0025 (5) |
C10A | 0.0287 (6) | 0.0239 (6) | 0.0411 (7) | −0.0019 (5) | −0.0072 (5) | −0.0013 (5) |
C11A | 0.0304 (7) | 0.0355 (7) | 0.0385 (7) | 0.0033 (5) | −0.0030 (6) | −0.0084 (6) |
C12A | 0.0276 (6) | 0.0276 (6) | 0.0393 (7) | −0.0002 (5) | −0.0049 (5) | −0.0056 (5) |
Cl1B | 0.0359 (2) | 0.0490 (2) | 0.0512 (2) | −0.00034 (16) | 0.01216 (16) | 0.00508 (18) |
O1B | 0.0296 (5) | 0.0288 (5) | 0.0421 (6) | −0.0036 (4) | 0.0024 (4) | 0.0014 (4) |
O2B | 0.0365 (6) | 0.0362 (5) | 0.0509 (6) | −0.0063 (4) | 0.0073 (5) | −0.0127 (5) |
C1B | 0.0249 (6) | 0.0224 (6) | 0.0289 (6) | 0.0012 (4) | −0.0045 (5) | 0.0052 (5) |
C2B | 0.0282 (6) | 0.0271 (6) | 0.0369 (7) | −0.0019 (5) | −0.0059 (5) | −0.0003 (5) |
C3B | 0.0250 (6) | 0.0303 (7) | 0.0463 (8) | −0.0035 (5) | −0.0036 (5) | 0.0042 (6) |
C4B | 0.0248 (6) | 0.0321 (7) | 0.0362 (7) | 0.0033 (5) | 0.0005 (5) | 0.0084 (5) |
C5B | 0.0299 (6) | 0.0313 (7) | 0.0322 (7) | 0.0020 (5) | −0.0043 (5) | −0.0003 (5) |
C6B | 0.0240 (6) | 0.0281 (6) | 0.0330 (7) | −0.0018 (5) | −0.0052 (5) | 0.0030 (5) |
C7B | 0.0261 (6) | 0.0253 (6) | 0.0309 (6) | 0.0024 (5) | −0.0046 (5) | 0.0031 (5) |
O1A—C5A | 1.424 (2) | C9A—H9AA | 0.9700 |
O1A—C6A | 1.3777 (17) | C9A—H9AB | 0.9700 |
O2A—C4A | 1.3753 (17) | C9A—C10A | 1.508 (2) |
O2A—C5A | 1.4281 (19) | C10A—H10A | 0.9700 |
N1A—C1A | 1.4640 (17) | C10A—H10B | 0.9700 |
N1A—C9A | 1.4658 (16) | C11A—H11A | 0.9700 |
N1A—C12A | 1.4578 (17) | C11A—H11B | 0.9700 |
N2A—H2AA | 0.9000 | C11A—C12A | 1.510 (2) |
N2A—H2AB | 0.9000 | C12A—H12A | 0.9700 |
N2A—C10A | 1.4818 (17) | C12A—H12B | 0.9700 |
N2A—C11A | 1.4829 (18) | Cl1B—C4B | 1.7391 (14) |
C1A—H1AA | 0.9700 | O1B—C7B | 1.2573 (16) |
C1A—H1AB | 0.9700 | O2B—C7B | 1.2554 (16) |
C1A—C2A | 1.5069 (19) | C1B—C2B | 1.3916 (18) |
C2A—C3A | 1.4019 (19) | C1B—C6B | 1.3873 (18) |
C2A—C8A | 1.382 (2) | C1B—C7B | 1.5079 (18) |
C3A—H3A | 0.9300 | C2B—H2B | 0.9300 |
C3A—C4A | 1.3619 (19) | C2B—C3B | 1.386 (2) |
C4A—C6A | 1.3820 (19) | C3B—H3B | 0.9300 |
C5A—H5AA | 0.9700 | C3B—C4B | 1.380 (2) |
C5A—H5AB | 0.9700 | C4B—C5B | 1.382 (2) |
C6A—C7A | 1.357 (2) | C5B—H5B | 0.9300 |
C7A—H7A | 0.9300 | C5B—C6B | 1.3896 (19) |
C7A—C8A | 1.394 (2) | C6B—H6B | 0.9300 |
C8A—H8A | 0.9300 | ||
C6A—O1A—C5A | 104.75 (11) | N1A—C9A—C10A | 110.67 (11) |
C4A—O2A—C5A | 104.70 (12) | H9AA—C9A—H9AB | 108.1 |
C1A—N1A—C9A | 110.44 (11) | C10A—C9A—H9AA | 109.5 |
C12A—N1A—C1A | 110.11 (11) | C10A—C9A—H9AB | 109.5 |
C12A—N1A—C9A | 109.66 (10) | N2A—C10A—C9A | 110.53 (11) |
H2AA—N2A—H2AB | 108.1 | N2A—C10A—H10A | 109.5 |
C10A—N2A—H2AA | 109.5 | N2A—C10A—H10B | 109.5 |
C10A—N2A—H2AB | 109.5 | C9A—C10A—H10A | 109.5 |
C10A—N2A—C11A | 110.60 (10) | C9A—C10A—H10B | 109.5 |
C11A—N2A—H2AA | 109.5 | H10A—C10A—H10B | 108.1 |
C11A—N2A—H2AB | 109.5 | N2A—C11A—H11A | 109.6 |
N1A—C1A—H1AA | 109.1 | N2A—C11A—H11B | 109.6 |
N1A—C1A—H1AB | 109.1 | N2A—C11A—C12A | 110.45 (12) |
N1A—C1A—C2A | 112.49 (11) | H11A—C11A—H11B | 108.1 |
H1AA—C1A—H1AB | 107.8 | C12A—C11A—H11A | 109.6 |
C2A—C1A—H1AA | 109.1 | C12A—C11A—H11B | 109.6 |
C2A—C1A—H1AB | 109.1 | N1A—C12A—C11A | 110.74 (11) |
C3A—C2A—C1A | 119.20 (13) | N1A—C12A—H12A | 109.5 |
C8A—C2A—C1A | 121.06 (13) | N1A—C12A—H12B | 109.5 |
C8A—C2A—C3A | 119.71 (13) | C11A—C12A—H12A | 109.5 |
C2A—C3A—H3A | 121.4 | C11A—C12A—H12B | 109.5 |
C4A—C3A—C2A | 117.16 (13) | H12A—C12A—H12B | 108.1 |
C4A—C3A—H3A | 121.4 | C2B—C1B—C7B | 120.21 (12) |
O2A—C4A—C6A | 109.64 (12) | C6B—C1B—C2B | 119.24 (12) |
C3A—C4A—O2A | 127.79 (13) | C6B—C1B—C7B | 120.56 (11) |
C3A—C4A—C6A | 122.46 (13) | C1B—C2B—H2B | 119.6 |
O1A—C5A—O2A | 107.89 (12) | C3B—C2B—C1B | 120.80 (13) |
O1A—C5A—H5AA | 110.1 | C3B—C2B—H2B | 119.6 |
O1A—C5A—H5AB | 110.1 | C2B—C3B—H3B | 120.7 |
O2A—C5A—H5AA | 110.1 | C4B—C3B—C2B | 118.69 (13) |
O2A—C5A—H5AB | 110.1 | C4B—C3B—H3B | 120.7 |
H5AA—C5A—H5AB | 108.4 | C3B—C4B—Cl1B | 118.85 (11) |
O1A—C6A—C4A | 109.57 (13) | C3B—C4B—C5B | 121.83 (13) |
C7A—C6A—O1A | 128.82 (13) | C5B—C4B—Cl1B | 119.31 (11) |
C7A—C6A—C4A | 121.54 (13) | C4B—C5B—H5B | 120.6 |
C6A—C7A—H7A | 121.6 | C4B—C5B—C6B | 118.77 (13) |
C6A—C7A—C8A | 116.78 (13) | C6B—C5B—H5B | 120.6 |
C8A—C7A—H7A | 121.6 | C1B—C6B—C5B | 120.64 (12) |
C2A—C8A—C7A | 122.33 (14) | C1B—C6B—H6B | 119.7 |
C2A—C8A—H8A | 118.8 | C5B—C6B—H6B | 119.7 |
C7A—C8A—H8A | 118.8 | O1B—C7B—C1B | 118.33 (12) |
N1A—C9A—H9AA | 109.5 | O2B—C7B—O1B | 124.75 (13) |
N1A—C9A—H9AB | 109.5 | O2B—C7B—C1B | 116.92 (12) |
O1A—C6A—C7A—C8A | −176.43 (14) | C6A—C7A—C8A—C2A | 1.1 (2) |
O2A—C4A—C6A—O1A | 0.07 (16) | C8A—C2A—C3A—C4A | 1.3 (2) |
O2A—C4A—C6A—C7A | −177.15 (13) | C9A—N1A—C1A—C2A | 174.49 (12) |
N1A—C1A—C2A—C3A | −49.87 (18) | C9A—N1A—C12A—C11A | −59.59 (14) |
N1A—C1A—C2A—C8A | 132.26 (14) | C10A—N2A—C11A—C12A | −55.32 (15) |
N1A—C9A—C10A—N2A | −57.53 (14) | C11A—N2A—C10A—C9A | 55.29 (14) |
N2A—C11A—C12A—N1A | 57.83 (15) | C12A—N1A—C1A—C2A | −64.26 (15) |
C1A—N1A—C9A—C10A | −179.02 (11) | C12A—N1A—C9A—C10A | 59.46 (14) |
C1A—N1A—C12A—C11A | 178.69 (11) | Cl1B—C4B—C5B—C6B | −178.09 (10) |
C1A—C2A—C3A—C4A | −176.59 (13) | C1B—C2B—C3B—C4B | 1.0 (2) |
C1A—C2A—C8A—C7A | 175.95 (13) | C2B—C1B—C6B—C5B | −2.03 (19) |
C2A—C3A—C4A—O2A | 175.68 (13) | C2B—C1B—C7B—O1B | −165.32 (12) |
C2A—C3A—C4A—C6A | 0.0 (2) | C2B—C1B—C7B—O2B | 14.80 (18) |
C3A—C2A—C8A—C7A | −1.9 (2) | C2B—C3B—C4B—Cl1B | 177.00 (10) |
C3A—C4A—C6A—O1A | 176.46 (13) | C2B—C3B—C4B—C5B | −1.9 (2) |
C3A—C4A—C6A—C7A | −0.8 (2) | C3B—C4B—C5B—C6B | 0.8 (2) |
C4A—O2A—C5A—O1A | 18.16 (18) | C4B—C5B—C6B—C1B | 1.22 (19) |
C4A—C6A—C7A—C8A | 0.2 (2) | C6B—C1B—C2B—C3B | 0.89 (19) |
C5A—O1A—C6A—C4A | 11.18 (16) | C6B—C1B—C7B—O1B | 14.36 (18) |
C5A—O1A—C6A—C7A | −171.86 (16) | C6B—C1B—C7B—O2B | −165.52 (12) |
C5A—O2A—C4A—C3A | 172.60 (15) | C7B—C1B—C2B—C3B | −179.42 (12) |
C5A—O2A—C4A—C6A | −11.25 (16) | C7B—C1B—C6B—C5B | 178.29 (11) |
C6A—O1A—C5A—O2A | −18.11 (17) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2A—H2AA···O1Bi | 0.90 | 1.87 | 2.7606 (15) | 171 |
N2A—H2AB···O2Bii | 0.90 | 1.78 | 2.6684 (16) | 169 |
C10A—H10A···O2Biii | 0.97 | 2.57 | 3.1974 (17) | 122 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+1, −y+3/2, z−1/2; (iii) −x+1, −y+2, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N2A—H2AA···O1Bi | 0.90 | 1.87 | 2.7606 (15) | 170.9 |
N2A—H2AB···O2Bii | 0.90 | 1.78 | 2.6684 (16) | 168.9 |
C10A—H10A···O2Biii | 0.97 | 2.57 | 3.1974 (17) | 122.2 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+1, −y+3/2, z−1/2; (iii) −x+1, −y+2, −z+1. |
Acknowledgements
CNK thanks the University of Mysore for research facilities and is also grateful to the Principal, Maharani's Science College for Women, Mysore, for giving permission to undertake research. JPJ acknowledges the NSF–MRI program (grant No. CHE-1039027) for funds to purchase the X-ray diffractometer.
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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.
1-(3,4-Methylenedioxybenzyl)piperazine or 1-piperonylpiperazine is a psychoactive drug of the piperazine class and is used to synthesise the drug, piribedil, an antiparkinsonian agent (Millan et al., 2001). Piperonylpiperazine derivatives also have α-adrenergic antagonist properties (Gobert et al., 2003) and peripheral vasodilator properties (Gilbert et al., 1968). Piperazines are among the most important building blocks in today's drug discovery and are found in biologically active compounds across a number of different therapeutic areas (Brockunier et al., 2004; Bogatcheva et al., 2006). A review of the current pharmacological and toxicological information for piperazine derivatives is described (Elliott, 2011). The crystal structure of an N-piperonyl analogue of the atypical antipsychotic clozapine (Capuano et al., 2000) is reported. In continuation of our work on salts of piperonylpiperazines, this paper reports the crystal structure of the title compound (I).
The asymmetric unit of (I) consists of a 1-piperonylpiperazinium cation and a p-chlorobenzoate anion (Fig. 1). The piperazine ring in the cation adopts a slightly disordered chair conformation (puckering parameters Q, θ, and φ = 0.5761 (14) Å , 177.7 (2) ° and 177 (4) °; (Cremer & Pople, 1975). The dioxole group is in a slightly distorted envelope configuration (puckering parameters Q and φ = 0.1693 (15) Å and 36.1 (5) ° with atom C5A displaced by 0.2683 (18) Å from the plane through the other four atoms). The piperonyl ring system and the piperazine rings are twisted with respect to each other as reflected in the N1A-C1A-C2A-C8A torsion angle of 132.2 (5)°. In the anion, the mean plane of the carboxylate group is twisted from that of the benzene ring by 14.8 (9)°. Bond lengths are in normal ranges (Allen et al., 1987). In the crystal, N—H···O hydrogen bonds and a weak C10A—H10A···O2Biii intermolecular interactions are observed which influence the crystal packing stability forming 1-D chains along [0 1 0] (Fig. 2).