1,3-Bis[4-(dimethyl­amino)benz­yl]-4,5,6,7-tetra­hydro-1H-1,3-diazepan-2-ium chloride

Arslan, H.; VanDerveer, D.; Gök, Y.; Özdemir, İ.; Çetinkaya, B.

doi:10.1107/S1600536808041603

organic compounds

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ISSN: 2056-9890

Volume 65| Part 1| January 2009| Pages o109-o110

doi:10.1107/S1600536808041603

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1,3-Bis[4-(dimethylamino)benzyl]-4,5,6,7-tetrahydro-1H-1,3-diazepan-2-ium chloride

Hakan Arslan,^a,^b ^* Don VanDerveer,^c Yetkin Gök,^d İsmail Özdemir ^d and Bekir Çetinkaya ^e

^aDepartment of Natural Sciences, Fayetteville State University, Fayetteville, NC 28301, USA, ^bDepartment of Chemistry, Faculty of Pharmacy, Mersin University, Mersin, TR 33169, Turkey, ^cDepartment of Chemistry, Clemson University, Clemson, SC 29634, USA, ^dDepartment of Chemistry, Faculty of Science and Arts, İnönü University, Malatya, TR 44280, Turkey, and ^eDepartment of Chemistry, Faculty of Science, Ege University, Bornova-İzmir, TR 35100, Turkey
^*Correspondence e-mail: hakan.arslan.acad@gmail.com

(Received 12 November 2008; accepted 8 December 2008; online 13 December 2008)

The title N-heterocyclic carbene derivative, C₂₃H₃₃N₄⁺·Cl⁻, has been synthesized and characterized by elemental analysis, ¹H and ¹³C NMR, IR spectroscopy and a single-crystal X-ray diffraction study. Ions of the title compound are linked by three C—H⋯Cl interactions. The seven-membered 1,3-diazepane ring has a form intermediate between twist-chair and twist-boat.

Related literature

For the synthesis, see: Özdemir et al. (2005 ); Yaşar et al. (2008 ). For general background, see: Hermann (2002 ); Littke & Fu (2002 ); Evans & Boeyens (1989 ). For puckering parameters, see: Cremer & Pople (1975 ). For related compounds, see: Arslan et al. (2007a ,b ,c ). For general background to the use of N-heterocyclic carbenes as phosphine mimics and in catalysis, see: Arduengo & Krafczyk (1998 ); Dullius et al. (1998 ); Glorius (2007 ); Hermann & Köcher (1997 ); Nolan (2006 ); Regitz (1996 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₂₃H₃₃N₄⁺·Cl⁻
M_r = 400.98
Orthorhombic, P b c n
a = 22.663 (5) Å
b = 10.081 (2) Å
c = 9.6368 (19) Å
V = 2201.7 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.19 mm⁻¹
T = 153 (2) K
0.46 × 0.12 × 0.07 mm

Data collection

Rigaku Mercury CCD diffractometer
Absorption correction: multi-scan (REQAB; Jacobson, 1998 ) T_min = 0.918, T_max = 0.987
14704 measured reflections
1947 independent reflections
1481 reflections with I > 2σ(I)
R_int = 0.053

Refinement

R[F² > 2σ(F²)] = 0.059
wR(F²) = 0.160
S = 1.10
1947 reflections
130 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯Cl1ⁱ	0.96	2.53	3.486 (4)	180
C2—H2A⋯Cl1ⁱⁱ	0.96	2.82	3.688 (3)	151
C4—H4A⋯Cl1ⁱⁱ	0.96	2.81	3.682 (3)	152
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) x, y, z+1.

Data collection: CrystalClear (Rigaku/MSC, 2001 ); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808041603/hg2445sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808041603/hg2445Isup2.hkl

checkCIF report

Comment top

N-heterocyclic carbenes, which can be considered phosphine mimics, have attracted considerable attentionas possible alternatives for widely used phosphine ligands (Regitz, 1996; Hermann & Köcher, 1997; Arduengo & Krafczyk, 1998; Dullius et al., 1998; Evans & Boeyens, 1989; Hermann, 2002; Littke & Fu, 2002). N-heterocyclic carbene-containing metal complexes have also revealed excellent catalytic properties in a wide range of metal-catalyzed transformations (Glorius, 2007; Nolan, 2006). Catalysts containing these ligands are useful in Heck, Suzuki and Sonogashira couplings, Buchwald Hartwig amination, olefin metathesis, hydroformylation and hydrogenation.

In recent years, we have pursued investigations on the synthesis, characterization, crystal structure, and catalytic activities of new N-heterocyclic carbene derivatives (Yaşar et al., 2008; Arslan et al., 2007a, 2007b, 2007c). In the present work, we report the preparation and characterization of a novel N-heterocyclic carbene derivative, 1,3-bis(4-(dimethylamino)benzyl)-4,5,6,7-tetrahydro-1H-1,3-diazepin-2-ium chloride, (I). The ligand was purified by re-crystallization from an ethanol:diethylether mixture (1:2) and was characterized by elemental analysis and ¹H and ¹³C-NMR spectroscopy. The analytical and spectroscopic data are consistent with the proposed structure given in Scheme 1.

The molecular structure of the title compound, (I), is depicted in Fig. 1. The structure consists of a 1,3-bis(4-(dimethylamino)benzyl)-4,5,6,7-tetrahydro-1H-1,3-diazepin-2-ium cation and a Cl^-anion. All bond lengths are in normal ranges (Allen et al., 1987). A seven-membered ring should have the chair, the boat, the twist chair or the twist boat according to Cremer & Pople (1975). The conformation of a seven-membered ring can be numerically described by four ring puckering parameters, q₂, q₃, ϕ₂ and ϕ₃. The 1,3-diazepane ring exhibits a puckered conformation, with puckering parameters Cremer & Pople (1975), q₂= 0.374 (3) Å, q₃ = 0.462 (3) Å, ϕ₂= 347.1 (4) °, ϕ₃= 115.7 (3)°, and Q_T= 0.595 (3) Å. The largest deviations from the mean plane are 0.403 (3) Å for atoms C3 and C3A. q₂should be 0 for a 100% twist chair form. According to Cremer & Pople ring-puckering analysis results, the 1,3-diazepane seven-membered ring can be accurately described as an intermediate form between the 44% twist chair form and the 55% twist boat form.

The crystal packing is shown in Fig. 2. Although there are no intramolecular D—H···A contacts, intermolecular C—H···Cl hydrogen bonds link the molecules of (I) into one-dimensional chains extending along the [010] direction (Fig. 3, Table 1) (Macrae et al., 2006).

Related literature top

For the synthesis, see: Özdemir et al. (2005); Yaşar et al. (2008). For general background, see: Hermann (2002); Littke & Fu (2002); Evans & Boeyens (1989). For puckering parameters, see: Cremer & Pople (1975). For related compounds, see: Arslan et al. (2007a,b,c). For related literature, see: Arduengo & Krafczyk (1998); Dullius et al. (1998); Glorius (2007); Hermann & Köcher (1997); Nolan (2006); Regitz (1996). For bond-length data, see: Allen et al. (1987).

Experimental top

To a solution of 1,4-bis(p-dimethylaminobenzylamino)butane (1 mmol) CH(OEt)₃ (30 ml), NH₄Cl (1 mmol) was added; the reaction mixture was heated for 18 h at 100 °C (Scheme 2). A white solid was precipitated. Then, the precipitate was crystallized from EtOH-Et₂O (1:2) mixture (Özdemir et al., 2005). 1,3-bis(4-(dimethylamino)benzyl)-4,5,6,7-tetrahydro-1H-1,3-diazepin-2-ium chloride: Yield: 3.11 g (92%), M.p. 247–248 °C. ¹H NMR (300.13 MHz, DMSO) δ = 1.68 (quintet, J = 6.8 Hz, 4H, NCH₂CH₂CH₂CH₂N), 2.89 (s, 12H, p-(CH₃)₂NC₆H₄CH₂), 3.52 (t, J = 6.8 Hz, 4H, NCH₂CH₂CH₂CH₂N), 4.54 (s, 4H, p-(CH₃)₂NC₆H₄CH₂), 6.73 and 7.27 (d, J =8.4 Hz, 8H, p-(CH₃)₂NC₆H₄CH₂), 8.87 (s,1H, 2-CH). ¹³C{¹H}NMR (75.47 MHz, DMSO): δ = 24.7, 48.7 (NCH₂CH₂CH₂CH₂N), 40.7 (p-(CH₃)₂NC₆H₄CH₂), 60.1 (p-(CH₃)₂NC₆H₄CH₂), 112.9, 122.2, 130.1, 151.1 (p-(CH₃)₂NC₆H₄CH₂), 158.3 (2-CH). Anal. Calcd. for C₂₃H₃₃N₄Cl: C, 68.89; H, 8.29; N, 13.97. Found: C, 68.88; H, 8.30; N, 13.94.

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2001); cell refinement: CrystalClear (Rigaku/MSC, 2001); data reduction: CrystalClear (Rigaku/MSC, 2001); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atom-numbering scheme and displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. A packing diagram for (I).
	Fig. 3. Part of the crystal structure of (I), showing the formation of linear chains of hydrogen-bonded (dashed lines) cations and anions along the [010] direction.
	Fig. 4. The formation of the title compound.

1,3-Bis[4-(dimethylamino)benzyl]-4,5,6,7-tetrahydro-1H-1,3- diazepan-2-ium chloride top

Crystal data top

C₂₃H₃₃N₄⁺·Cl⁻	F(000) = 864
M_r = 400.98	D_x = 1.210 Mg m⁻³
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 5004 reflections
a = 22.663 (5) Å	θ = 3.1–26.4°
b = 10.081 (2) Å	µ = 0.19 mm⁻¹
c = 9.6368 (19) Å	T = 153 K
V = 2201.7 (8) Å³	Rod, colorless
Z = 4	0.46 × 0.12 × 0.07 mm

Data collection top

Rigaku Mercury CCD diffractometer	1947 independent reflections
Radiation source: Sealed Tube	1481 reflections with I > 2σ(I)
Graphite Monochromator monochromator	R_int = 0.053
Detector resolution: 14.6306 pixels mm^-1	θ_max = 25.1°, θ_min = 3.1°
ω scans	h = −27→23
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	k = −12→11
T_min = 0.918, T_max = 0.987	l = −11→11
14704 measured reflections

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.160	H-atom parameters constrained
S = 1.10	w = 1/[σ²(F_o²) + (0.0629P)² + 3.1587P] where P = (F_o² + 2F_c²)/3
1947 reflections	(Δ/σ)_max < 0.001
130 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₂₃H₃₃N₄⁺·Cl⁻	V = 2201.7 (8) Å³
M_r = 400.98	Z = 4
Orthorhombic, Pbcn	Mo Kα radiation
a = 22.663 (5) Å	µ = 0.19 mm⁻¹
b = 10.081 (2) Å	T = 153 K
c = 9.6368 (19) Å	0.46 × 0.12 × 0.07 mm

Data collection top

Rigaku Mercury CCD diffractometer	1947 independent reflections
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	1481 reflections with I > 2σ(I)
T_min = 0.918, T_max = 0.987	R_int = 0.053
14704 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	0 restraints
wR(F²) = 0.160	H-atom parameters constrained
S = 1.10	Δρ_max = 0.28 e Å⁻³
1947 reflections	Δρ_min = −0.30 e Å⁻³
130 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
Cl1	0.5000	0.27328 (9)	0.2500	0.0326 (3)
N1	0.53058 (10)	0.3281 (2)	0.8530 (2)	0.0263 (5)
N2	0.81399 (11)	0.3446 (3)	0.8340 (3)	0.0465 (8)
C1	0.5000	0.3809 (4)	0.7500	0.0234 (8)
H1	0.5000	0.4761	0.7500	0.028*
C2	0.54103 (13)	0.1885 (3)	0.8905 (3)	0.0320 (7)
H2A	0.5391	0.1810	0.9897	0.038*
H2B	0.5805	0.1656	0.8631	0.038*
C3	0.49952 (13)	0.0887 (3)	0.8287 (3)	0.0299 (7)
H3A	0.4602	0.1074	0.8599	0.036*
H3B	0.5100	0.0019	0.8616	0.036*
C4	0.56701 (12)	0.4207 (3)	0.9380 (3)	0.0286 (6)
H4A	0.5588	0.4062	1.0345	0.034*
H4B	0.5564	0.5104	0.9160	0.034*
C5	0.63188 (12)	0.4015 (3)	0.9123 (3)	0.0280 (6)
C6	0.65910 (13)	0.4560 (3)	0.7968 (3)	0.0361 (7)
H6	0.6359	0.5068	0.7327	0.043*
C7	0.71893 (14)	0.4394 (3)	0.7709 (4)	0.0410 (8)
H7	0.7364	0.4791	0.6902	0.049*
C8	0.75396 (13)	0.3648 (3)	0.8622 (3)	0.0359 (7)
C9	0.72698 (13)	0.3100 (3)	0.9785 (3)	0.0359 (7)
H9	0.7500	0.2585	1.0425	0.043*
C10	0.66696 (13)	0.3289 (3)	1.0031 (3)	0.0316 (7)
H10	0.6494	0.2909	1.0846	0.038*
C11	0.84333 (15)	0.4411 (4)	0.7441 (5)	0.0577 (11)
H11A	0.8243	0.4424	0.6552	0.087*
H11B	0.8840	0.4166	0.7328	0.087*
H11C	0.8410	0.5276	0.7854	0.087*
C12	0.85025 (15)	0.2829 (4)	0.9408 (4)	0.0569 (11)
H12A	0.8501	0.3374	1.0225	0.085*
H12B	0.8900	0.2737	0.9074	0.085*
H12C	0.8346	0.1970	0.9628	0.085*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0410 (6)	0.0223 (5)	0.0347 (5)	0.000	0.0031 (4)	0.000
N1	0.0280 (12)	0.0207 (11)	0.0302 (12)	−0.0008 (9)	0.0021 (10)	−0.0010 (10)
N2	0.0300 (14)	0.0458 (17)	0.064 (2)	−0.0016 (12)	0.0035 (13)	−0.0117 (15)
C1	0.0210 (17)	0.0196 (18)	0.030 (2)	0.000	0.0053 (16)	0.000
C2	0.0399 (16)	0.0206 (14)	0.0356 (16)	0.0035 (12)	−0.0043 (13)	0.0019 (12)
C3	0.0376 (15)	0.0191 (13)	0.0331 (16)	0.0013 (12)	0.0030 (13)	0.0035 (11)
C4	0.0303 (14)	0.0239 (14)	0.0315 (15)	0.0006 (11)	0.0013 (12)	−0.0053 (12)
C5	0.0300 (15)	0.0251 (14)	0.0290 (15)	−0.0003 (11)	0.0000 (11)	−0.0032 (12)
C6	0.0331 (16)	0.0372 (17)	0.0379 (17)	0.0004 (13)	0.0013 (13)	0.0056 (14)
C7	0.0386 (17)	0.0415 (18)	0.0430 (19)	−0.0055 (14)	0.0073 (14)	0.0058 (15)
C8	0.0299 (15)	0.0327 (16)	0.0450 (17)	−0.0011 (12)	0.0007 (14)	−0.0093 (14)
C9	0.0353 (16)	0.0350 (17)	0.0373 (17)	0.0069 (13)	−0.0062 (13)	−0.0036 (14)
C10	0.0348 (16)	0.0299 (15)	0.0300 (15)	−0.0002 (12)	0.0000 (12)	−0.0013 (13)
C11	0.0358 (18)	0.045 (2)	0.092 (3)	−0.0136 (15)	0.0185 (19)	−0.014 (2)
C12	0.0326 (17)	0.067 (3)	0.071 (3)	0.0097 (17)	−0.0076 (18)	−0.024 (2)

Geometric parameters (Å, º) top

N1—C1	1.322 (3)	C5—C6	1.386 (4)
N1—C2	1.472 (3)	C5—C10	1.391 (4)
N1—C4	1.491 (3)	C6—C7	1.389 (4)
N2—C8	1.402 (4)	C6—H6	0.9600
N2—C12	1.456 (5)	C7—C8	1.404 (5)
N2—C11	1.462 (5)	C7—H7	0.9600
C1—N1ⁱ	1.322 (3)	C8—C9	1.391 (4)
C1—H1	0.9600	C9—C10	1.394 (4)
C2—C3	1.501 (4)	C9—H9	0.9600
C2—H2A	0.9600	C10—H10	0.9600
C2—H2B	0.9600	C11—H11A	0.9599
C3—C3ⁱ	1.517 (6)	C11—H11B	0.9599
C3—H3A	0.9600	C11—H11C	0.9599
C3—H3B	0.9600	C12—H12A	0.9599
C4—C5	1.503 (4)	C12—H12B	0.9599
C4—H4A	0.9600	C12—H12C	0.9599
C4—H4B	0.9600

C1—N1—C2	130.8 (3)	C10—C5—C4	121.5 (3)
C1—N1—C4	116.8 (2)	C5—C6—C7	122.1 (3)
C2—N1—C4	112.0 (2)	C5—C6—H6	119.0
C8—N2—C12	118.2 (3)	C7—C6—H6	119.0
C8—N2—C11	117.3 (3)	C6—C7—C8	120.3 (3)
C12—N2—C11	116.5 (3)	C6—C7—H7	119.9
N1ⁱ—C1—N1	132.6 (4)	C8—C7—H7	119.9
N1ⁱ—C1—H1	113.7	C9—C8—N2	121.7 (3)
N1—C1—H1	113.7	C9—C8—C7	118.0 (3)
N1—C2—C3	116.3 (2)	N2—C8—C7	120.3 (3)
N1—C2—H2A	108.2	C8—C9—C10	120.8 (3)
C3—C2—H2A	108.2	C8—C9—H9	119.6
N1—C2—H2B	108.2	C10—C9—H9	119.6
C3—C2—H2B	108.2	C5—C10—C9	121.5 (3)
H2A—C2—H2B	107.4	C5—C10—H10	119.2
C2—C3—C3ⁱ	112.8 (2)	C9—C10—H10	119.2
C2—C3—H3A	109.0	N2—C11—H11A	109.5
C3ⁱ—C3—H3A	109.0	N2—C11—H11B	109.5
C2—C3—H3B	109.0	H11A—C11—H11B	109.5
C3ⁱ—C3—H3B	109.0	N2—C11—H11C	109.5
H3A—C3—H3B	107.8	H11A—C11—H11C	109.5
N1—C4—C5	111.8 (2)	H11B—C11—H11C	109.5
N1—C4—H4A	109.3	N2—C12—H12A	109.5
C5—C4—H4A	109.3	N2—C12—H12B	109.5
N1—C4—H4B	109.3	H12A—C12—H12B	109.5
C5—C4—H4B	109.3	N2—C12—H12C	109.5
H4A—C4—H4B	107.9	H12A—C12—H12C	109.5
C6—C5—C10	117.4 (3)	H12B—C12—H12C	109.5
C6—C5—C4	121.1 (3)

C2—N1—C1—N1ⁱ	−0.7 (2)	C12—N2—C8—C9	−10.0 (4)
C4—N1—C1—N1ⁱ	171.0 (2)	C11—N2—C8—C9	−157.9 (3)
C1—N1—C2—C3	−18.0 (4)	C12—N2—C8—C7	171.5 (3)
C4—N1—C2—C3	170.0 (2)	C11—N2—C8—C7	23.6 (5)
N1—C2—C3—C3ⁱ	59.9 (4)	C6—C7—C8—C9	−0.5 (5)
C1—N1—C4—C5	−109.3 (2)	C6—C7—C8—N2	178.0 (3)
C2—N1—C4—C5	63.9 (3)	N2—C8—C9—C10	−178.6 (3)
N1—C4—C5—C6	80.0 (3)	C7—C8—C9—C10	−0.1 (5)
N1—C4—C5—C10	−100.1 (3)	C6—C5—C10—C9	−0.8 (4)
C10—C5—C6—C7	0.2 (5)	C4—C5—C10—C9	179.3 (3)
C4—C5—C6—C7	−179.9 (3)	C8—C9—C10—C5	0.7 (5)
C5—C6—C7—C8	0.4 (5)

Symmetry code: (i) −x+1, y, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···Cl1ⁱⁱ	0.96	2.53	3.486 (4)	180
C2—H2A···Cl1ⁱⁱⁱ	0.96	2.82	3.688 (3)	151
C4—H4A···Cl1ⁱⁱⁱ	0.96	2.81	3.682 (3)	152

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

Experimental details

Crystal data
Chemical formula	C₂₃H₃₃N₄⁺·Cl⁻
M_r	400.98
Crystal system, space group	Orthorhombic, Pbcn
Temperature (K)	153
a, b, c (Å)	22.663 (5), 10.081 (2), 9.6368 (19)
V (Å³)	2201.7 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.19
Crystal size (mm)	0.46 × 0.12 × 0.07

Data collection
Diffractometer	Rigaku Mercury CCD diffractometer
Absorption correction	Multi-scan (REQAB; Jacobson, 1998)
T_min, T_max	0.918, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections	14704, 1947, 1481
R_int	0.053
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.160, 1.10
No. of reflections	1947
No. of parameters	130
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.30

Computer programs: CrystalClear (Rigaku/MSC, 2001), SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2006).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···Cl1ⁱ	0.96	2.53	3.486 (4)	180.0
C2—H2A···Cl1ⁱⁱ	0.96	2.82	3.688 (3)	151.0
C4—H4A···Cl1ⁱⁱ	0.96	2.81	3.682 (3)	152.0

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

Acknowledgements

We thank the Technological and Scientific Research Council of Turkey TÜBİTAK-CNRS [TBAG-U/181 (106 T716)] and İnonu University research fund (BAP 2008/03 Güdümlü) for financial support.

References

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Volume 65| Part 1| January 2009| Pages o109-o110

doi:10.1107/S1600536808041603

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

1,3-Bis[4-(di­methyl­amino)benz­yl]-4,5,6,7-tetra­hydro-1H-1,3-diazepan-2-ium chloride

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

1,3-Bis[4-(dimethylamino)benzyl]-4,5,6,7-tetrahydro-1H-1,3-diazepan-2-ium chloride