4-Benzyl­piperazin-1-ium chloride chloro­form solvate

Nema, M.G.; Varga, R.A.; Silvestru, C.; Breunig, H.J.

doi:10.1107/S1600536808022587

organic compounds

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Volume 64| Part 8| August 2008| Page o1585

doi:10.1107/S1600536808022587

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4-Benzylpiperazin-1-ium chloride chloroform solvate

Mihai G. Nema,^a Richard A. Varga,^a ^* Cristian Silvestru ^a and Hans J. Breunig ^b

^aFaculty of Chemistry and Chemical Engineering, Babes-Bolyai University, 11 Arany Janos Street, RO-400028, Cluj Napoca, Romania, and ^bInstitut für Anorganische und Physikalische Chemie, Universität Bremen, D-28334 Bremen, Germany
^*Correspondence e-mail: richy@chem.ubbcluj.ro

(Received 10 July 2008; accepted 18 July 2008; online 23 July 2008)

The ions of the title chloroform-solvated salt, C₁₁H₁₇N₂⁺·Cl⁻·CHCl₃, are linked by a strong N—H⋯Cl hydrogen bond; the solvent molecule also interacts with the chloride ion through a C—H⋯Cl hydrogen bond. Additionally, neighboring cations form weak hydrogen bonds to the anion, resulting in a supramolecular ribbon that runs along the a axis.

Related literature

For related literature, see Albinati et al. (1980 ); Antolini et al. (1981 , 1982 ); Osa et al. (2002 ); Tanaka et al. (2005 ).

Experimental

Crystal data

C₁₁H₁₇N₂⁺·Cl⁻·CHCl₃
M_r = 332.08
Triclinic, $[P \overline 1]$
a = 5.6053 (4) Å
b = 9.4889 (9) Å
c = 15.303 (2) Å
α = 100.980 (8)°
β = 90.957 (7)°
γ = 93.219 (7)°
V = 797.51 (15) Å³
Z = 2
Mo Kα radiation
μ = 0.73 mm⁻¹
T = 173 (2) K
0.40 × 0.32 × 0.30 mm

Data collection

Siemens P4 diffractometer
Absorption correction: none
4013 measured reflections
2967 independent reflections
2811 reflections with I > 2σ(I)
R_int = 0.015
3 standard reflections every 197 reflections intensity decay: none

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.128
S = 1.07
2967 reflections
175 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.56 e Å⁻³
Δρ_min = −0.72 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N⋯Cl1	0.85 (2)	2.30 (2)	3.140 (2)	169 (2)
C12—H12⋯Cl1	0.89 (3)	2.60 (3)	3.401 (2)	151 (2)
N2—H2N⋯Cl1ⁱ	0.88 (2)	2.26 (2)	3.096 (2)	159 (2)
C10—H10A⋯Cl1ⁱⁱ	0.97	2.74	3.684 (2)	165
Symmetry codes: (i) x-1, y, z; (ii) -x+1, -y, -z+1.

Data collection: XSCANS (Siemens, 1994 ); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2008 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808022587/ng2473sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808022587/ng2473Isup2.hkl

checkCIF report

Comment top

Derivatives of piperazine are useful compounds because of their biological activity (Osa et al., 2002). Trimetazidine is a clinically antianginal agent (Tanaka et al., 2005). A compound of the type (NBzpipzH₂)₂CuCl₆ (NBzpipzH₂ = N-benzylpiperazinium dication) was reported (Antolini et al., 1982) and the preparation of mercury(III) compounds (NbzpipzH)Hg₂X₅ (NbzpipzH = N-benzylpiperazinium monocation; X = Cl, Br) is known (Albinati, et al., 1980, Antolini et al., 1981).

The title compound (Fig.1) is formed by C₁₁H₁₇N₂⁺ cation and Cl^- anion connected through a strong N—H···Cl^- hydrogen bond [H1N···Cl1 = 2.30 (2) Å, N2—H1N···Cl1 = 169 (2)°] and crystallizes with a CHCl₃ molecule bonded to the Cl^- through a hydrogen bond [H12···Cl1 = 2.60 (3) Å, C12—H12···Cl1 = 151 (2)°]. Intermolecular hydrogen bonds link the Cl^- anion to two aditional cations (Table 1) resulting in a double chain-like supramolecular arrangement along the a axis. In crystal there are no interactions between the chains (Fig.2).

Related literature top

For related literature, see Albinati et al. (1980); Antolini et al. (1981, 1982); Osa et al. (2002); Tanaka et al. (2005).

Experimental top

The compound was obtained as a by-product of the reaction between [2-{HN(CH₂CH₂)₂NCH₂}C₆H₄]Li and BiCl₃. Crystals were grown by slow difusion from chloroform / n-hexane (1:5).

¹H NMR (CDCl₃, 200 MHz, 291 K): δ 2.74 (4H, m, N—CH₂—CH₂—N), 3.20 (4H, m, N—CH₂—CH₂—N), 3.55 (2H, s, C₆H₅—CH₂—N), 7.29 (5H, m, C₆H₅), 8.90 (2H, s, br, NH₂). ¹³C NMR (CDCl₃, 50 MHz, 291 K): δ 43.59 (s, N—CH₂—CH₂—N), 49.47 (s, N—CH₂—CH₂—N), 62.39 (s, C₆H₅—CH₂—N), 127.53 (s, C-p), 128.45 (s, C-m), 128.95 (s, C-o), 136.89 (s, C-i).

Computing details top

Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS (Siemens, 1994); data reduction: XSCANS (Siemens, 1994); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2006); software used to prepare material for publication: publCIF (Westrip, 2008).

Figures top

	Fig. 1. : View of the title compound showing the atom-numbering (50% probability thermal ellipsoids).
	Fig. 2. : Crystal packing of the title compound showing the supramolecular arrays (hydrogen bonds as dashes lines).

4-Benzylpiperazin-1-ium chloride chloroform solvate top

Crystal data top

C₁₁H₁₇N₂⁺·Cl⁻·CHCl₃	Z = 2
M_r = 332.08	F(000) = 344
Triclinic, P1	D_x = 1.383 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.6053 (4) Å	Cell parameters from 44 reflections
b = 9.4889 (9) Å	θ = 8.5–25.1°
c = 15.303 (2) Å	µ = 0.73 mm⁻¹
α = 100.980 (8)°	T = 173 K
β = 90.957 (7)°	Block, colorless
γ = 93.219 (7)°	0.40 × 0.32 × 0.30 mm
V = 797.51 (15) Å³

Data collection top

Siemens P4 diffractometer	R_int = 0.015
Radiation source: sealed tube	θ_max = 25.5°, θ_min = 2.7°
Graphite monochromator	h = −6→2
2θ–/ω scans	k = −11→11
4013 measured reflections	l = −18→18
2967 independent reflections	3 standard reflections every 197 reflections
2811 reflections with I > 2σ(I)	intensity decay: none

Refinement top

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.128	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ²(F_o²) + (0.0804P)² + 0.5046P] where P = (F_o² + 2F_c²)/3
2967 reflections	(Δ/σ)_max < 0.001
175 parameters	Δρ_max = 0.56 e Å⁻³
2 restraints	Δρ_min = −0.72 e Å⁻³

Crystal data top

C₁₁H₁₇N₂⁺·Cl⁻·CHCl₃	γ = 93.219 (7)°
M_r = 332.08	V = 797.51 (15) Å³
Triclinic, P1	Z = 2
a = 5.6053 (4) Å	Mo Kα radiation
b = 9.4889 (9) Å	µ = 0.73 mm⁻¹
c = 15.303 (2) Å	T = 173 K
α = 100.980 (8)°	0.40 × 0.32 × 0.30 mm
β = 90.957 (7)°

Data collection top

Siemens P4 diffractometer	R_int = 0.015
4013 measured reflections	3 standard reflections every 197 reflections
2967 independent reflections	intensity decay: none
2811 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.047	2 restraints
wR(F²) = 0.128	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.56 e Å⁻³
2967 reflections	Δρ_min = −0.72 e Å⁻³
175 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl4	1.23828 (12)	0.13191 (10)	0.29039 (5)	0.0610 (2)
C12	0.9555 (4)	0.1520 (2)	0.24518 (15)	0.0300 (5)
Cl1	0.70662 (8)	0.21020 (5)	0.44910 (3)	0.02735 (17)
Cl2	0.94353 (13)	0.32245 (6)	0.21628 (5)	0.0472 (2)
Cl3	0.87877 (13)	0.01645 (7)	0.15238 (4)	0.0450 (2)
N1	0.3777 (3)	0.37270 (18)	0.71793 (11)	0.0228 (4)
N2	0.2108 (3)	0.25651 (19)	0.53939 (12)	0.0251 (4)
C2	0.6514 (4)	0.2552 (3)	0.89764 (16)	0.0353 (5)
H2	0.7872	0.2308	0.8654	0.042*
C6	0.2964 (4)	0.3838 (3)	0.91871 (15)	0.0324 (5)
H6	0.1924	0.4466	0.9010	0.039*
C11	0.3743 (4)	0.2181 (2)	0.68279 (14)	0.0275 (4)
H11A	0.3486	0.1659	0.7308	0.033*
H11B	0.5274	0.1940	0.6572	0.033*
C1	0.5004 (4)	0.3496 (2)	0.87052 (13)	0.0264 (4)
C8	0.4281 (4)	0.4505 (2)	0.64568 (14)	0.0260 (4)
H8A	0.5804	0.4242	0.6202	0.031*
H8B	0.4386	0.5531	0.6690	0.031*
C9	0.2325 (4)	0.4145 (2)	0.57441 (14)	0.0273 (4)
H9A	0.0819	0.4460	0.5991	0.033*
H9B	0.2689	0.4647	0.5262	0.033*
C5	0.2475 (4)	0.3245 (3)	0.99313 (16)	0.0380 (5)
H5	0.1106	0.3477	1.0249	0.046*
C10	0.1780 (4)	0.1739 (2)	0.61243 (14)	0.0280 (4)
H10A	0.1808	0.0718	0.5884	0.034*
H10B	0.0239	0.1917	0.6389	0.034*
C4	0.4008 (5)	0.2314 (3)	1.02029 (15)	0.0389 (6)
H4	0.3681	0.1925	1.0705	0.047*
C7	0.5559 (4)	0.4164 (2)	0.79057 (14)	0.0286 (5)
H7A	0.5634	0.5203	0.8085	0.034*
H7B	0.7117	0.3888	0.7691	0.034*
C3	0.6033 (5)	0.1962 (3)	0.97243 (17)	0.0415 (6)
H3	0.7071	0.1332	0.9902	0.050*
H1N	0.339 (4)	0.232 (3)	0.5127 (17)	0.035 (7)*
H2N	0.089 (4)	0.235 (3)	0.5012 (16)	0.039 (7)*
H12	0.848 (5)	0.145 (3)	0.2865 (19)	0.039 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl4	0.0309 (4)	0.0937 (6)	0.0588 (5)	0.0100 (3)	−0.0096 (3)	0.0144 (4)
C12	0.0240 (10)	0.0381 (12)	0.0271 (10)	0.0006 (9)	0.0046 (9)	0.0044 (9)
Cl1	0.0176 (3)	0.0367 (3)	0.0265 (3)	0.0034 (2)	0.00211 (19)	0.0023 (2)
Cl2	0.0565 (4)	0.0326 (3)	0.0527 (4)	0.0009 (3)	0.0136 (3)	0.0079 (3)
Cl3	0.0589 (4)	0.0362 (3)	0.0360 (3)	−0.0047 (3)	−0.0030 (3)	−0.0007 (2)
N1	0.0214 (8)	0.0232 (8)	0.0230 (8)	−0.0007 (6)	0.0010 (7)	0.0032 (6)
N2	0.0167 (8)	0.0323 (9)	0.0248 (9)	0.0026 (7)	0.0004 (7)	0.0014 (7)
C2	0.0256 (11)	0.0460 (13)	0.0335 (12)	0.0042 (9)	−0.0001 (9)	0.0053 (10)
C6	0.0274 (11)	0.0396 (12)	0.0286 (11)	0.0031 (9)	−0.0004 (9)	0.0020 (9)
C11	0.0290 (11)	0.0248 (10)	0.0283 (10)	0.0021 (8)	−0.0002 (8)	0.0043 (8)
C1	0.0231 (10)	0.0306 (10)	0.0226 (10)	−0.0044 (8)	−0.0037 (8)	0.0001 (8)
C8	0.0254 (10)	0.0253 (10)	0.0272 (10)	−0.0021 (8)	0.0027 (8)	0.0056 (8)
C9	0.0264 (10)	0.0274 (10)	0.0291 (10)	0.0035 (8)	0.0008 (8)	0.0074 (8)
C5	0.0335 (12)	0.0491 (14)	0.0282 (11)	−0.0033 (10)	0.0062 (9)	0.0003 (10)
C10	0.0268 (10)	0.0250 (10)	0.0312 (11)	−0.0029 (8)	0.0000 (8)	0.0040 (8)
C4	0.0443 (14)	0.0468 (13)	0.0246 (10)	−0.0096 (11)	−0.0027 (10)	0.0082 (10)
C7	0.0230 (10)	0.0333 (11)	0.0273 (10)	−0.0053 (8)	−0.0017 (8)	0.0023 (9)
C3	0.0418 (14)	0.0471 (14)	0.0380 (13)	0.0035 (11)	−0.0078 (11)	0.0146 (11)

Geometric parameters (Å, º) top

Cl4—C12	1.753 (2)	C11—H11A	0.9700
C12—Cl3	1.755 (2)	C11—H11B	0.9700
C12—Cl2	1.761 (2)	C1—C7	1.510 (3)
C12—H12	0.89 (3)	C8—C9	1.511 (3)
N1—C11	1.462 (3)	C8—H8A	0.9700
N1—C8	1.464 (2)	C8—H8B	0.9700
N1—C7	1.465 (3)	C9—H9A	0.9700
N2—C9	1.490 (3)	C9—H9B	0.9700
N2—C10	1.491 (3)	C5—C4	1.381 (4)
N2—H1N	0.852 (17)	C5—H5	0.9300
N2—H2N	0.881 (17)	C10—H10A	0.9700
C2—C1	1.381 (3)	C10—H10B	0.9700
C2—C3	1.391 (3)	C4—C3	1.383 (4)
C2—H2	0.9300	C4—H4	0.9300
C6—C5	1.387 (3)	C7—H7A	0.9700
C6—C1	1.391 (3)	C7—H7B	0.9700
C6—H6	0.9300	C3—H3	0.9300
C11—C10	1.511 (3)

Cl4—C12—Cl3	111.93 (13)	C9—C8—H8A	109.6
Cl4—C12—Cl2	110.52 (13)	N1—C8—H8B	109.6
Cl3—C12—Cl2	110.17 (12)	C9—C8—H8B	109.6
Cl4—C12—H12	108.1 (19)	H8A—C8—H8B	108.2
Cl3—C12—H12	107.5 (19)	N2—C9—C8	110.19 (16)
Cl2—C12—H12	108.5 (18)	N2—C9—H9A	109.6
C11—N1—C8	109.08 (16)	C8—C9—H9A	109.6
C11—N1—C7	111.36 (16)	N2—C9—H9B	109.6
C8—N1—C7	110.31 (16)	C8—C9—H9B	109.6
C9—N2—C10	111.57 (16)	H9A—C9—H9B	108.1
C9—N2—H1N	108.5 (19)	C4—C5—C6	120.4 (2)
C10—N2—H1N	108.6 (18)	C4—C5—H5	119.8
C9—N2—H2N	109.8 (18)	C6—C5—H5	119.8
C10—N2—H2N	109.3 (18)	N2—C10—C11	110.24 (17)
H1N—N2—H2N	109 (3)	N2—C10—H10A	109.6
C1—C2—C3	120.9 (2)	C11—C10—H10A	109.6
C1—C2—H2	119.5	N2—C10—H10B	109.6
C3—C2—H2	119.5	C11—C10—H10B	109.6
C5—C6—C1	120.3 (2)	H10A—C10—H10B	108.1
C5—C6—H6	119.8	C5—C4—C3	119.6 (2)
C1—C6—H6	119.8	C5—C4—H4	120.2
N1—C11—C10	110.42 (17)	C3—C4—H4	120.2
N1—C11—H11A	109.6	N1—C7—C1	112.66 (17)
C10—C11—H11A	109.6	N1—C7—H7A	109.1
N1—C11—H11B	109.6	C1—C7—H7A	109.1
C10—C11—H11B	109.6	N1—C7—H7B	109.1
H11A—C11—H11B	108.1	C1—C7—H7B	109.1
C2—C1—C6	118.9 (2)	H7A—C7—H7B	107.8
C2—C1—C7	120.9 (2)	C4—C3—C2	119.8 (2)
C6—C1—C7	120.3 (2)	C4—C3—H3	120.1
N1—C8—C9	110.12 (16)	C2—C3—H3	120.1
N1—C8—H8A	109.6

C8—N1—C11—C10	−61.9 (2)	C1—C6—C5—C4	0.1 (4)
C7—N1—C11—C10	176.10 (16)	C9—N2—C10—C11	−53.5 (2)
C3—C2—C1—C6	−0.8 (3)	N1—C11—C10—N2	57.5 (2)
C3—C2—C1—C7	178.5 (2)	C6—C5—C4—C3	−0.5 (4)
C5—C6—C1—C2	0.5 (3)	C11—N1—C7—C1	−63.9 (2)
C5—C6—C1—C7	−178.8 (2)	C8—N1—C7—C1	174.83 (17)
C11—N1—C8—C9	62.1 (2)	C2—C1—C7—N1	115.9 (2)
C7—N1—C8—C9	−175.25 (17)	C6—C1—C7—N1	−64.7 (3)
C10—N2—C9—C8	53.8 (2)	C5—C4—C3—C2	0.2 (4)
N1—C8—C9—N2	−58.0 (2)	C1—C2—C3—C4	0.4 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N···Cl1	0.85 (2)	2.30 (2)	3.140 (2)	169 (2)
C12—H12···Cl1	0.89 (3)	2.60 (3)	3.401 (2)	151 (2)
N2—H2N···Cl1ⁱ	0.88 (2)	2.26 (2)	3.096 (2)	159 (2)
C10—H10A···Cl1ⁱⁱ	0.97	2.74	3.684 (2)	165

Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₁H₁₇N₂⁺·Cl⁻·CHCl₃
M_r	332.08
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	5.6053 (4), 9.4889 (9), 15.303 (2)
α, β, γ (°)	100.980 (8), 90.957 (7), 93.219 (7)
V (Å³)	797.51 (15)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.73
Crystal size (mm)	0.40 × 0.32 × 0.30

Data collection
Diffractometer	Siemens P4 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	4013, 2967, 2811
R_int	0.015
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.128, 1.07
No. of reflections	2967
No. of parameters	175
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.56, −0.72

Computer programs: XSCANS (Siemens, 1994), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg & Putz, 2006), publCIF (Westrip, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N···Cl1	0.85 (2)	2.30 (2)	3.140 (2)	169 (2)
C12—H12···Cl1	0.89 (3)	2.60 (3)	3.401 (2)	151 (2)
N2—H2N···Cl1ⁱ	0.88 (2)	2.26 (2)	3.096 (2)	159 (2)
C10—H10A···Cl1ⁱⁱ	0.97	2.74	3.684 (2)	165

Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y, −z+1.

Acknowledgements

The financial support provided by the Ministry of Education and Research of Romania (Excellency Research Program, project CEx-05-D11-16/2005; grant No. CNCSIS TD-80/2007) is greatly appreciated.

References

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