Crystal structure of N1-benzyl-N1,N2,N2-tri­methyl­ethane-1,2-diaminium dichloride

Singh, P.; Singh, H.B.; Butcher, R.J.

doi:10.1107/S1600536814015797

organic compounds

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ISSN: 2056-9890

Volume 70| Part 9| September 2014| Pages o911-o912

doi:10.1107/S1600536814015797

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Crystal structure of N¹-benzyl-N¹,N²,N²-trimethylethane-1,2-diaminium dichloride

Pushpendra Singh,^a Harkesh B. Singh ^a and Ray J. Butcher ^b ^*

^aDepartment of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai, 400076, India, and ^bDepartment of Chemistry, Howard University, 525 College Street NW, Washington DC 20059, USA
^*Correspondence e-mail: rbutcher99@yahoo.com

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 27 June 2014; accepted 7 July 2014; online 1 August 2014)

In the title molecular salt, C₁₂H₂₂N₂²⁺·2Cl⁻, which was obtained as a by-product in the attempted synthesis of a mercury derivative, the conformation of the N—C—C—N bond in the cation is anti [torsion angle = 175.1 (10)°]. In the crystal, the cations are linked to the anions by N—H⋯Cl hydrogen bonds, generating ion-triplets. These are linked by numerous weak C—H⋯Cl interactions, generating a three-dimensional network. The structure was refined as an inversion twin.

Keywords: crystal structure; hydrogen bonds; C—H⋯Cl interactions; ion-triplets; inversion twin.

CCDC reference: 1012363

1. Related literature

For further synthetic details, see: Rietveld et al. (1994 ). For the application of the parent diamine as a precursor of anti-histamine derivatives for therapeutic use, see: Gardner & Stevens (1949 ); Fox & Wenner (1951 ); For a related structure, see: Manjare et al. (2014 ).

2. Experimental

2.1. Crystal data

C₁₂H₂₂N₂²⁺·2Cl⁻
M_r = 265.21
Monoclinic, P 2₁
a = 5.6744 (7) Å
b = 22.384 (3) Å
c = 5.9991 (7) Å
β = 105.372 (12)°
V = 734.72 (16) Å³
Z = 2
Cu Kα radiation
μ = 3.79 mm⁻¹
T = 123 K
0.49 × 0.16 × 0.13 mm

2.2. Data collection

Agilent Xcalibur, Ruby, Gemini diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ) T_min = 0.273, T_max = 1.000
2002 measured reflections
1986 independent reflections
1961 reflections with I > 2σ(I)
R_int = 0.000

2.3. Refinement

R[F² > 2σ(F²)] = 0.082
wR(F²) = 0.229
S = 1.13
1986 reflections
149 parameters
7 restraints
H-atom parameters constrained
Δρ_max = 1.15 e Å⁻³
Δρ_min = −0.62 e Å⁻³
Refined as an inversion twin
Absolute structure parameter: 0.25 (7)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯Cl1	1.00	2.11	3.107 (8)	179
N2—H2B⋯Cl2	1.00	2.18	3.148 (11)	163
C7—H7B⋯Cl1ⁱ	0.99	2.92	3.749 (13)	142
C8—H8A⋯Cl2ⁱⁱ	0.98	2.93	3.893 (10)	168
C8—H8B⋯Cl1ⁱ	0.98	2.79	3.690 (11)	154
C8—H8C⋯Cl1ⁱⁱⁱ	0.98	2.88	3.486 (12)	121
C9—H9A⋯Cl1^iv	0.99	2.74	3.711 (12)	168
C10—H10A⋯Cl1	0.99	2.98	3.682 (11)	129
C10—H10B⋯Cl2ⁱⁱ	0.99	2.78	3.750 (13)	168
C11—H11B⋯Cl1^iv	0.98	2.89	3.831 (17)	161
C12—H12B⋯Cl2ⁱⁱ	0.98	2.89	3.842 (15)	166
C12—H12C⋯Cl2^v	0.98	2.88	3.747 (13)	147
Symmetry codes: (i) x-1, y, z-1; (ii) x+1, y, z; (iii) x, y, z-1; (iv) x-1, y, z; (v) x+1, y, z+1.

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

CCDC reference: 1012363

Crystal structure: contains datablock I. DOI: 10.1107/S1600536814015797/hb7244sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814015797/hb7244Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814015797/hb7244Isup3.cml

checkCIF report

Experimental top

The starting material, o-diamine-substituted aryl bromide, N¹-(2-bromobenzyl)-N¹,N²,N²-trimethylethane-1,2-diamine, can be prepared by the reaction of N¹,N¹,N²-trimethylethane-1,2-diamine and ortho-bromobenzylbromide (Rietveld et al., 1994). This ligand is moisture sensitive and is difficult to purify by column chromatography. However, it could be easily purified by vacuum distillation. The moisture sensitive ligand when treated with n-BuLi in THF produced the lithiated product (2) which when treated with AlCl₃ afforded the title salt.

A stirred solution of N¹-(2-bromobenzyl)-N¹,N²,N²-trimethylethane-1,2-diamine (1.10 ml, 5.34 mmol) in dry THF (15 ml) was treated dropwise with a 1.6 M solution of n-BuLi in hexane (3.80 ml, 6.15 mmol) via syringe under N₂ at 0°C. On stirring the reaction mixture for 2 h at this temperature the lithiated product (2) was obtained. To a freshly prepared 2 (1.10 ml, 5.34 mmol) in dry THF (15 ml) was added anhydrous aluminum trichloride (0.75 g, 5.70 mmol) under a brisk flow of N₂ gas and stirring was continued for an additional 6 h at room temperature. The reaction mixture was then removed from the N₂ line and evaporated to dryness to give a colourless hygroscopic solid. The solid was extracted with dry ether. The organic phase was separated, dried over Na₂SO₄, and filtered. The filtrate was evaporated to dryness to give a colourless crystalline solid of the title salt (0.48, 34% yield). ¹H NMR (CDCl₃) δ 2.72 (s, NMe₂), 2.38 (s, NMe), 2.95 (t, 2H), 3.13 (3, 2H), 3.65 (s, CH₂), 5.48 (s, br 2NH), 7.31-7.39 (m, 5H-aryl); ¹³C NMR (DMSO-d₆) δ 41.52, 43.40, 51.86, 54.32, 61.69, 67. 34, 127.50, 128.51, 129.43, 138.18.

Refinement top

H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms with a C—H distances of 0.95 and 0.99 Å and an N—H distance of 1.00 U_iso(H) = 1.2U_eq(C, N) and 0.98 Å for CH₃ [U_iso(H)= 1.5U_eq(C)]

Related literature top

For further synthetic details, see: Rietveld et al. (1994). For the application of the parent diamine as a precursor of anti-histamine derivatives for therapeutic use, see: Gardner & Stevens (1949); Fox & Wenner (1951); For a related structure, see: Manjare et al. (2014).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of C₁₂H₂₂N₂.2Cl showing 30% probability displacement ellipsoids and the N—H···Cl hydrogen bonds (shown as dashed lines).
	Fig. 2. The packing for C₁₂H₂₂N₂.2Cl viewed along the b axis showing the linking of the cations and anions into a three-dimensional array by an extensive network of C—H···Cl interactions (shown as dashed bonds).

N¹-Benzyl-N¹,N²,N²-trimethylethane-1,2-diaminium dichloride top

Crystal data top

C₁₂H₂₂N₂²⁺·2Cl⁻	F(000) = 284
M_r = 265.21	D_x = 1.199 Mg m⁻³
Monoclinic, P2₁	Cu Kα radiation, λ = 1.54178 Å
a = 5.6744 (7) Å	Cell parameters from 1555 reflections
b = 22.384 (3) Å	θ = 4.0–76.4°
c = 5.9991 (7) Å	µ = 3.79 mm⁻¹
β = 105.372 (12)°	T = 123 K
V = 734.72 (16) Å³	Needle, colorless
Z = 2	0.49 × 0.16 × 0.13 mm

Data collection top

Agilent Xcalibur, Ruby, Gemini diffractometer	1961 reflections with I > 2σ(I)
Detector resolution: 10.5081 pixels mm^-1	R_int = 0.000
ω scans	θ_max = 76.6°, θ_min = 4.0°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	h = −7→6
T_min = 0.273, T_max = 1.000	k = −27→21
2002 measured reflections	l = 0→7
1986 independent reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.082	H-atom parameters constrained
wR(F²) = 0.229	w = 1/[σ²(F_o²) + (0.1591P)² + 1.0863P] where P = (F_o² + 2F_c²)/3
S = 1.13	(Δ/σ)_max < 0.001
1986 reflections	Δρ_max = 1.15 e Å⁻³
149 parameters	Δρ_min = −0.62 e Å⁻³
7 restraints	Absolute structure: Refined as an inversion twin.
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.25 (7)

Crystal data top

C₁₂H₂₂N₂²⁺·2Cl⁻	V = 734.72 (16) Å³
M_r = 265.21	Z = 2
Monoclinic, P2₁	Cu Kα radiation
a = 5.6744 (7) Å	µ = 3.79 mm⁻¹
b = 22.384 (3) Å	T = 123 K
c = 5.9991 (7) Å	0.49 × 0.16 × 0.13 mm
β = 105.372 (12)°

Data collection top

Agilent Xcalibur, Ruby, Gemini diffractometer	1986 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	1961 reflections with I > 2σ(I)
T_min = 0.273, T_max = 1.000	R_int = 0.000
2002 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.082	H-atom parameters constrained
wR(F²) = 0.229	Δρ_max = 1.15 e Å⁻³
S = 1.13	Δρ_min = −0.62 e Å⁻³
1986 reflections	Absolute structure: Refined as an inversion twin.
149 parameters	Absolute structure parameter: 0.25 (7)
7 restraints

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. Refined as a 2-component inversion twin.

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

	x	y	z	U_iso*/U_eq
Cl1	0.5443 (3)	0.30227 (7)	1.3350 (2)	0.0313 (4)
Cl2	−0.5635 (2)	0.48206 (5)	0.67629 (19)	0.0219 (3)
N1	0.0818 (16)	0.3087 (4)	0.9195 (14)	0.052 (2)
H1A	0.2296	0.3060	1.0540	0.063*
N2	−0.0884 (18)	0.4633 (5)	1.083 (2)	0.061 (2)
H2B	−0.2225	0.4640	0.9363	0.074*
C1	0.092 (2)	0.1998 (6)	0.814 (2)	0.065 (3)
C2	−0.012 (3)	0.1787 (6)	0.583 (2)	0.078 (4)
H2A	−0.1656	0.1919	0.4903	0.094*
C3	0.141 (3)	0.1344 (6)	0.500 (2)	0.075 (3)
H3A	0.0818	0.1180	0.3493	0.090*
C4	0.359 (3)	0.1172 (6)	0.629 (3)	0.092 (4)
H4A	0.4563	0.0907	0.5670	0.110*
C5	0.446 (3)	0.1374 (7)	0.855 (3)	0.094 (5)
H5A	0.6003	0.1239	0.9458	0.113*
C6	0.310 (2)	0.1772 (6)	0.950 (2)	0.074 (3)
H6A	0.3662	0.1887	1.1075	0.088*
C7	−0.044 (3)	0.2487 (6)	0.896 (2)	0.067 (3)
H7A	−0.0677	0.2372	1.0479	0.080*
H7B	−0.2077	0.2525	0.7861	0.080*
C8	0.171 (2)	0.3228 (4)	0.7060 (17)	0.050 (2)
H8A	0.2488	0.3622	0.7239	0.074*
H8B	0.0318	0.3227	0.5683	0.074*
H8C	0.2896	0.2925	0.6890	0.074*
C9	−0.065 (2)	0.3554 (5)	0.967 (2)	0.057 (3)
H9A	−0.1454	0.3416	1.0862	0.069*
H9B	−0.1955	0.3646	0.8253	0.069*
C10	0.079 (2)	0.4127 (6)	1.0534 (19)	0.058 (3)
H10A	0.1997	0.4047	1.2031	0.069*
H10B	0.1706	0.4249	0.9411	0.069*
C11	−0.205 (3)	0.4576 (7)	1.257 (3)	0.075 (4)
H11A	−0.0833	0.4579	1.4077	0.113*
H11B	−0.2958	0.4198	1.2383	0.113*
H11C	−0.3186	0.4910	1.2494	0.113*
C12	0.045 (3)	0.5223 (6)	1.088 (2)	0.066 (3)
H12A	−0.0741	0.5546	1.0381	0.099*
H12B	0.1517	0.5202	0.9838	0.099*
H12C	0.1441	0.5304	1.2459	0.099*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0262 (7)	0.0399 (11)	0.0259 (7)	−0.0014 (7)	0.0034 (6)	0.0010 (6)
Cl2	0.0176 (6)	0.0285 (7)	0.0176 (6)	−0.0026 (6)	0.0012 (4)	0.0048 (5)
N1	0.049 (4)	0.063 (5)	0.038 (4)	−0.010 (4)	−0.001 (3)	0.007 (4)
N2	0.044 (4)	0.060 (6)	0.084 (6)	0.002 (4)	0.024 (4)	0.005 (4)
C1	0.065 (6)	0.067 (7)	0.067 (6)	0.001 (5)	0.026 (5)	−0.006 (5)
C2	0.082 (9)	0.080 (8)	0.065 (7)	−0.004 (7)	0.007 (6)	−0.004 (6)
C3	0.091 (8)	0.053 (6)	0.081 (7)	−0.008 (7)	0.023 (6)	−0.012 (6)
C4	0.107 (10)	0.045 (6)	0.143 (13)	0.000 (7)	0.067 (9)	−0.017 (7)
C5	0.084 (9)	0.055 (6)	0.130 (12)	0.005 (8)	0.006 (8)	−0.012 (9)
C6	0.067 (7)	0.083 (9)	0.071 (7)	−0.003 (6)	0.019 (6)	0.002 (6)
C7	0.076 (7)	0.070 (7)	0.060 (6)	−0.003 (6)	0.025 (5)	−0.002 (5)
C8	0.060 (6)	0.049 (6)	0.034 (4)	−0.005 (4)	0.002 (4)	0.002 (3)
C9	0.050 (5)	0.063 (6)	0.060 (6)	0.006 (5)	0.016 (5)	0.003 (5)
C10	0.050 (5)	0.065 (6)	0.049 (5)	0.007 (5)	−0.004 (4)	0.009 (4)
C11	0.056 (6)	0.086 (8)	0.078 (7)	−0.009 (6)	0.007 (6)	−0.018 (6)
C12	0.061 (6)	0.068 (7)	0.063 (7)	0.011 (6)	0.006 (5)	0.006 (5)

Geometric parameters (Å, º) top

N1—C9	1.413 (15)	C5—H5A	0.9500
N1—C7	1.511 (17)	C6—H6A	0.9500
N1—C8	1.530 (14)	C7—H7A	0.9900
N1—H1A	1.0000	C7—H7B	0.9900
N2—C11	1.38 (2)	C8—H8A	0.9800
N2—C10	1.520 (16)	C8—H8B	0.9800
N2—C12	1.521 (17)	C8—H8C	0.9800
N2—H2B	1.0000	C9—C10	1.538 (16)
C1—C6	1.382 (18)	C9—H9A	0.9900
C1—C2	1.435 (18)	C9—H9B	0.9900
C1—C7	1.497 (18)	C10—H10A	0.9900
C2—C3	1.49 (2)	C10—H10B	0.9900
C2—H2A	0.9500	C11—H11A	0.9800
C3—C4	1.33 (2)	C11—H11B	0.9800
C3—H3A	0.9500	C11—H11C	0.9800
C4—C5	1.39 (2)	C12—H12A	0.9800
C4—H4A	0.9500	C12—H12B	0.9800
C5—C6	1.40 (2)	C12—H12C	0.9800

C9—N1—C7	112.7 (9)	C1—C7—H7B	108.7
C9—N1—C8	111.3 (9)	N1—C7—H7B	108.7
C7—N1—C8	111.0 (8)	H7A—C7—H7B	107.6
C9—N1—H1A	107.2	N1—C8—H8A	109.5
C7—N1—H1A	107.2	N1—C8—H8B	109.5
C8—N1—H1A	107.2	H8A—C8—H8B	109.5
C11—N2—C10	117.4 (11)	N1—C8—H8C	109.5
C11—N2—C12	113.6 (11)	H8A—C8—H8C	109.5
C10—N2—C12	109.0 (9)	H8B—C8—H8C	109.5
C11—N2—H2B	105.2	N1—C9—C10	113.1 (9)
C10—N2—H2B	105.2	N1—C9—H9A	109.0
C12—N2—H2B	105.2	C10—C9—H9A	109.0
C6—C1—C2	121.6 (13)	N1—C9—H9B	109.0
C6—C1—C7	122.1 (12)	C10—C9—H9B	109.0
C2—C1—C7	116.3 (12)	H9A—C9—H9B	107.8
C1—C2—C3	114.6 (13)	N2—C10—C9	111.4 (9)
C1—C2—H2A	122.7	N2—C10—H10A	109.3
C3—C2—H2A	122.7	C9—C10—H10A	109.3
C4—C3—C2	122.1 (13)	N2—C10—H10B	109.3
C4—C3—H3A	118.9	C9—C10—H10B	109.3
C2—C3—H3A	118.9	H10A—C10—H10B	108.0
C3—C4—C5	120.6 (15)	N2—C11—H11A	109.5
C3—C4—H4A	119.7	N2—C11—H11B	109.5
C5—C4—H4A	119.7	H11A—C11—H11B	109.5
C4—C5—C6	121.0 (14)	N2—C11—H11C	109.5
C4—C5—H5A	119.5	H11A—C11—H11C	109.5
C6—C5—H5A	119.5	H11B—C11—H11C	109.5
C1—C6—C5	119.7 (13)	N2—C12—H12A	109.5
C1—C6—H6A	120.1	N2—C12—H12B	109.5
C5—C6—H6A	120.1	H12A—C12—H12B	109.5
C1—C7—N1	114.2 (11)	N2—C12—H12C	109.5
C1—C7—H7A	108.7	H12A—C12—H12C	109.5
N1—C7—H7A	108.7	H12B—C12—H12C	109.5

C6—C1—C2—C3	−4 (2)	C2—C1—C7—N1	−108.9 (14)
C7—C1—C2—C3	174.3 (12)	C9—N1—C7—C1	172.2 (10)
C1—C2—C3—C4	−1 (2)	C8—N1—C7—C1	46.6 (13)
C2—C3—C4—C5	4 (2)	C7—N1—C9—C10	165.1 (9)
C3—C4—C5—C6	−1 (3)	C8—N1—C9—C10	−69.5 (11)
C2—C1—C6—C5	7 (2)	C11—N2—C10—C9	67.8 (13)
C7—C1—C6—C5	−171.5 (14)	C12—N2—C10—C9	−161.2 (10)
C4—C5—C6—C1	−4 (2)	N1—C9—C10—N2	175.1 (10)
C6—C1—C7—N1	69.3 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl1	1.00	2.11	3.107 (8)	179
N2—H2B···Cl2	1.00	2.18	3.148 (11)	163
C7—H7B···Cl1ⁱ	0.99	2.92	3.749 (13)	142
C8—H8A···Cl2ⁱⁱ	0.98	2.93	3.893 (10)	168
C8—H8B···Cl1ⁱ	0.98	2.79	3.690 (11)	154
C8—H8C···Cl1ⁱⁱⁱ	0.98	2.88	3.486 (12)	121
C9—H9A···Cl1^iv	0.99	2.74	3.711 (12)	168
C10—H10A···Cl1	0.99	2.98	3.682 (11)	129
C10—H10B···Cl2ⁱⁱ	0.99	2.78	3.750 (13)	168
C11—H11B···Cl1^iv	0.98	2.89	3.831 (17)	161
C12—H12B···Cl2ⁱⁱ	0.98	2.89	3.842 (15)	166
C12—H12C···Cl2^v	0.98	2.88	3.747 (13)	147

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl1	1.00	2.11	3.107 (8)	179
N2—H2B···Cl2	1.00	2.18	3.148 (11)	163
C7—H7B···Cl1ⁱ	0.99	2.92	3.749 (13)	142
C8—H8A···Cl2ⁱⁱ	0.98	2.93	3.893 (10)	168
C8—H8B···Cl1ⁱ	0.98	2.79	3.690 (11)	154
C8—H8C···Cl1ⁱⁱⁱ	0.98	2.88	3.486 (12)	121
C9—H9A···Cl1^iv	0.99	2.74	3.711 (12)	168
C10—H10A···Cl1	0.99	2.98	3.682 (11)	129
C10—H10B···Cl2ⁱⁱ	0.99	2.78	3.750 (13)	168
C11—H11B···Cl1^iv	0.98	2.89	3.831 (17)	161
C12—H12B···Cl2ⁱⁱ	0.98	2.89	3.842 (15)	166
C12—H12C···Cl2^v	0.98	2.88	3.747 (13)	147

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

Acknowledgements

RJB acknowledges the NSF–MRI program (grant No. CHE-0619278) for funds to purchase an X-ray diffractometer.

References

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Volume 70| Part 9| September 2014| Pages o911-o912

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