Crystal structure of N (1)-benzyl-N (1),N (2),N (2)-tri-methyl-ethane-1,2-diaminium dichloride.

In the title mol-ecular salt, C12H22N2 (2+)·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 inter-actions, generating a three-dimensional network. The structure was refined as an inversion twin.

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 ▶).

Experimental

Crystal data

C12H22N2 2+·2Cl−

M = 265.21

Monoclinic,

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

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

Refinement

R[F 2 > 2σ(F 2)] = 0.082

wR(F 2) = 0.229

S = 1.13

1986 reflections

149 parameters

7 restraints

H-atom parameters constrained

Δρmax = 1.15 e Å−3

Δρmin = −0.62 e Å−3

Refined as an inversion twin

Absolute structure parameter: 0.25 (7)

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 ▶).

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

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

Click here for additional data file.

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

Click here for additional data file.

12 22 2 . DOI: 10.1107/S1600536814015797/hb7244fig1.tif

The mol­ecular structure of C12H22N2·2Cl showing 30% probability displacement ellipsoids and the n class="Chemical">N—H⋯Cl hydrogen bonds (shown as dashed lines).

Click here for additional data file.

12 22 2 b . DOI: 10.1107/S1600536814015797/hb7244fig2.tif

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).

CCDC reference: 1012363

Additional supporting information: crystallographic information; 3D view; checkCIF report

C12H22N22+·2Cl−	F(000) = 284
Mr = 265.21	Dx = 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

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

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(Fo2) + (0.1591P)2 + 1.0863P] where P = (Fo2 + 2Fc2)/3
S = 1.13	(Δ/σ)max < 0.001
1986 reflections	Δρmax = 1.15 e Å−3
149 parameters	Δρmin = −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)

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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···Cl1iv	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···Cl1iv	0.98	2.89	3.831 (17)	161
C12—H12B···Cl2ii	0.98	2.89	3.842 (15)	166
C12—H12C···Cl2v	0.98	2.88	3.747 (13)	147

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⋯Cl1iv	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⋯Cl1iv	0.98	2.89	3.831 (17)	161
C12—H12B⋯Cl2ii	0.98	2.89	3.842 (15)	166
C12—H12C⋯Cl2v	0.98	2.88	3.747 (13)	147

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .