2,2-Dibenzyl-hydrazin-1-ium chloride.

In the title salt, C14H17N2(+)·Cl(-), the central N atom is pyramidal (sum of bond angles = 330.9°) and there is a near orthogonal relationship between the benzene rings [dihedral angle = 89.95 (10)°]. The crystal packing features N-H⋯Cl hydrogen bonds, which lead to a supra-molecular undulating ribbon along the a axis comprising edge-shared eight-membered {⋯HNH⋯Cl}2 synthons. The chains are connected into layers in the ab plane by C-H⋯π inter-actions.

Related literature

For background to the synthesis of S-substituted dithio­carbaza­tes and their metal complexes, see: Ravoof et al. (2010 ▶); Tayamon et al. (2012 ▶). For the synthesis, see: Tarafder et al. (2000 ▶). For the structure of the n class="Chemical">diphenyl analogue of the cation, see: Stender et al. (2003 ▶).

Experimental

Crystal data

C14H17N2 +·Cl−

M = 248.75

Triclinic,

a = 5.6155 (4) Å

b = 9.9804 (7) Å

c = 11.7302 (9) Å

α = 79.532 (6)°

β = 78.508 (6)°

γ = 83.550 (6)°

V = 631.54 (8) Å3

Z = 2

Cu Kα radiation

μ = 2.49 mm−1

T = 100 K

0.14 × 0.09 × 0.02 mm

Data collection

Oxford Diffraction Xcalibur Eos Gemini diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.72, T max = 0.95

6961 measured reflections

2407 independent reflections

2076 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.129

S = 1.07

2407 reflections

166 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.45 e Å−3

Δρmin = −0.24 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813003966/hb7036sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813003966/hb7036Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813003966/hb7036Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C14H17N2+·Cl−	Z = 2
Mr = 248.75	F(000) = 264
Triclinic, P1	Dx = 1.308 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54180 Å
a = 5.6155 (4) Å	Cell parameters from 3230 reflections
b = 9.9804 (7) Å	θ = 4–71°
c = 11.7302 (9) Å	µ = 2.49 mm−1
α = 79.532 (6)°	T = 100 K
β = 78.508 (6)°	Plate, colourless
γ = 83.550 (6)°	0.14 × 0.09 × 0.02 mm
V = 631.54 (8) Å3

Oxford Diffraction Xcalibur Eos Gemini diffractometer	2407 independent reflections
Radiation source: fine-focus sealed tube	2076 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
Detector resolution: 16.1952 pixels mm-1	θmax = 71.5°, θmin = 3.9°
ω scans	h = −6→6
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −12→11
Tmin = 0.72, Tmax = 0.95	l = −14→14
6961 measured reflections

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) = 0.129	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.079P)2 + 0.1383P] where P = (Fo2 + 2Fc2)/3
2407 reflections	(Δ/σ)max < 0.001
166 parameters	Δρmax = 0.45 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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.

	x	y	z	Uiso*/Ueq
Cl1	0.84514 (8)	0.01710 (5)	0.33994 (4)	0.02664 (19)
N1	0.2435 (3)	0.28342 (17)	0.37150 (14)	0.0250 (4)
N2	0.2870 (3)	0.13600 (18)	0.40100 (16)	0.0248 (4)
H1n	0.444 (5)	0.104 (3)	0.367 (2)	0.033 (6)*
H2n	0.264 (4)	0.109 (3)	0.486 (2)	0.034 (6)*
H3n	0.167 (5)	0.095 (3)	0.379 (2)	0.041 (7)*
C1	0.2203 (4)	0.3190 (2)	0.24543 (18)	0.0279 (5)
H1A	0.1843	0.4191	0.2271	0.033*
H1B	0.0782	0.2754	0.2346	0.033*
C2	0.4393 (4)	0.2781 (2)	0.15639 (17)	0.0250 (4)
C3	0.6219 (4)	0.3662 (2)	0.10779 (19)	0.0309 (5)
H3	0.6066	0.4551	0.1280	0.037*
C4	0.8266 (4)	0.3253 (2)	0.02986 (19)	0.0340 (5)
H4	0.9500	0.3863	−0.0029	0.041*
C5	0.8508 (4)	0.1958 (2)	0.00005 (19)	0.0313 (5)
H5	0.9908	0.1676	−0.0529	0.038*
C6	0.6703 (4)	0.1077 (2)	0.04771 (18)	0.0301 (5)
H6	0.6871	0.0185	0.0279	0.036*
C7	0.4638 (4)	0.1489 (2)	0.12462 (18)	0.0281 (5)
H7	0.3389	0.0884	0.1556	0.034*
C8	0.4435 (4)	0.3486 (2)	0.40018 (18)	0.0269 (5)
H8A	0.4279	0.4481	0.3709	0.032*
H8B	0.6021	0.3107	0.3601	0.032*
C9	0.4366 (4)	0.3245 (2)	0.53131 (18)	0.0244 (4)
C10	0.6359 (4)	0.2601 (2)	0.57891 (19)	0.0282 (5)
H10	0.7779	0.2302	0.5281	0.034*
C11	0.6301 (4)	0.2389 (2)	0.70000 (19)	0.0285 (5)
H11	0.7673	0.1944	0.7313	0.034*
C12	0.4247 (4)	0.2827 (2)	0.77478 (18)	0.0269 (5)
H12	0.4207	0.2693	0.8574	0.032*
C13	0.2239 (4)	0.3465 (2)	0.72795 (18)	0.0275 (5)
H13	0.0817	0.3759	0.7790	0.033*
C14	0.2303 (4)	0.3675 (2)	0.60783 (18)	0.0259 (4)
H14	0.0925	0.4117	0.5769	0.031*

	U11	U22	U33	U12	U13	U23
Cl1	0.0242 (3)	0.0312 (3)	0.0251 (3)	−0.00283 (19)	−0.00452 (19)	−0.0057 (2)
N1	0.0277 (9)	0.0256 (9)	0.0217 (9)	−0.0021 (7)	−0.0038 (7)	−0.0047 (7)
N2	0.0237 (10)	0.0277 (10)	0.0233 (9)	−0.0037 (7)	−0.0040 (7)	−0.0041 (7)
C1	0.0296 (11)	0.0293 (11)	0.0236 (10)	0.0006 (9)	−0.0047 (8)	−0.0032 (8)
C2	0.0274 (11)	0.0294 (11)	0.0186 (9)	−0.0006 (8)	−0.0065 (8)	−0.0035 (8)
C3	0.0404 (13)	0.0289 (11)	0.0240 (10)	−0.0048 (9)	−0.0060 (9)	−0.0048 (9)
C4	0.0356 (12)	0.0416 (14)	0.0242 (11)	−0.0113 (10)	−0.0013 (9)	−0.0035 (9)
C5	0.0276 (11)	0.0420 (13)	0.0237 (10)	0.0012 (9)	−0.0037 (8)	−0.0072 (9)
C6	0.0356 (12)	0.0308 (12)	0.0247 (10)	0.0016 (9)	−0.0072 (9)	−0.0073 (9)
C7	0.0299 (11)	0.0313 (11)	0.0236 (10)	−0.0043 (9)	−0.0058 (8)	−0.0037 (9)
C8	0.0278 (11)	0.0293 (11)	0.0234 (10)	−0.0066 (8)	−0.0010 (8)	−0.0054 (8)
C9	0.0249 (10)	0.0247 (10)	0.0243 (10)	−0.0071 (8)	−0.0016 (8)	−0.0057 (8)
C10	0.0245 (11)	0.0316 (11)	0.0279 (11)	−0.0033 (8)	0.0013 (8)	−0.0092 (9)
C11	0.0266 (11)	0.0279 (11)	0.0320 (11)	−0.0023 (8)	−0.0076 (9)	−0.0052 (9)
C12	0.0310 (11)	0.0291 (11)	0.0215 (10)	−0.0068 (9)	−0.0045 (8)	−0.0039 (8)
C13	0.0268 (11)	0.0280 (11)	0.0264 (11)	−0.0020 (8)	−0.0001 (8)	−0.0062 (8)
C14	0.0250 (10)	0.0256 (11)	0.0268 (10)	−0.0017 (8)	−0.0047 (8)	−0.0039 (8)

N1—N2	1.453 (2)	C6—C7	1.392 (3)
N1—C8	1.481 (3)	C6—H6	0.9500
N1—C1	1.485 (3)	C7—H7	0.9500
N2—H1n	0.94 (3)	C8—C9	1.506 (3)
N2—H2n	0.97 (3)	C8—H8A	0.9900
N2—H3n	0.93 (3)	C8—H8B	0.9900
C1—C2	1.516 (3)	C9—C10	1.391 (3)
C1—H1A	0.9900	C9—C14	1.395 (3)
C1—H1B	0.9900	C10—C11	1.392 (3)
C2—C7	1.391 (3)	C10—H10	0.9500
C2—C3	1.391 (3)	C11—C12	1.383 (3)
C3—C4	1.391 (3)	C11—H11	0.9500
C3—H3	0.9500	C12—C13	1.392 (3)
C4—C5	1.385 (3)	C12—H12	0.9500
C4—H4	0.9500	C13—C14	1.380 (3)
C5—C6	1.381 (3)	C13—H13	0.9500
C5—H5	0.9500	C14—H14	0.9500
N2—N1—C8	108.71 (15)	C7—C6—H6	119.8
N2—N1—C1	108.85 (15)	C2—C7—C6	120.4 (2)
C8—N1—C1	113.32 (16)	C2—C7—H7	119.8
N1—N2—H1n	112.5 (16)	C6—C7—H7	119.8
N1—N2—H2n	110.1 (14)	N1—C8—C9	110.82 (17)
H1n—N2—H2n	109 (2)	N1—C8—H8A	109.5
N1—N2—H3n	108.9 (16)	C9—C8—H8A	109.5
H1n—N2—H3n	112 (2)	N1—C8—H8B	109.5
H2n—N2—H3n	104 (2)	C9—C8—H8B	109.5
N1—C1—C2	116.42 (16)	H8A—C8—H8B	108.1
N1—C1—H1A	108.2	C10—C9—C14	118.43 (19)
C2—C1—H1A	108.2	C10—C9—C8	120.94 (18)
N1—C1—H1B	108.2	C14—C9—C8	120.63 (18)
C2—C1—H1B	108.2	C11—C10—C9	120.91 (19)
H1A—C1—H1B	107.3	C11—C10—H10	119.5
C7—C2—C3	118.77 (19)	C9—C10—H10	119.5
C7—C2—C1	119.93 (19)	C12—C11—C10	120.03 (19)
C3—C2—C1	121.27 (18)	C12—C11—H11	120.0
C4—C3—C2	120.7 (2)	C10—C11—H11	120.0
C4—C3—H3	119.7	C11—C12—C13	119.43 (19)
C2—C3—H3	119.7	C11—C12—H12	120.3
C5—C4—C3	120.1 (2)	C13—C12—H12	120.3
C5—C4—H4	119.9	C14—C13—C12	120.40 (18)
C3—C4—H4	119.9	C14—C13—H13	119.8
C6—C5—C4	119.7 (2)	C12—C13—H13	119.8
C6—C5—H5	120.2	C13—C14—C9	120.80 (19)
C4—C5—H5	120.2	C13—C14—H14	119.6
C5—C6—C7	120.4 (2)	C9—C14—H14	119.6
C5—C6—H6	119.8
N2—N1—C1—C2	−60.2 (2)	N2—N1—C8—C9	−66.5 (2)
C8—N1—C1—C2	60.9 (2)	C1—N1—C8—C9	172.31 (16)
N1—C1—C2—C7	87.6 (2)	N1—C8—C9—C10	122.1 (2)
N1—C1—C2—C3	−90.4 (2)	N1—C8—C9—C14	−58.4 (3)
C7—C2—C3—C4	−0.7 (3)	C14—C9—C10—C11	0.0 (3)
C1—C2—C3—C4	177.35 (19)	C8—C9—C10—C11	179.45 (19)
C2—C3—C4—C5	−0.2 (3)	C9—C10—C11—C12	−0.3 (3)
C3—C4—C5—C6	0.2 (3)	C10—C11—C12—C13	0.7 (3)
C4—C5—C6—C7	0.5 (3)	C11—C12—C13—C14	−0.7 (3)
C3—C2—C7—C6	1.5 (3)	C12—C13—C14—C9	0.4 (3)
C1—C2—C7—C6	−176.61 (18)	C10—C9—C14—C13	0.0 (3)
C5—C6—C7—C2	−1.4 (3)	C8—C9—C14—C13	−179.51 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N···Cl1	0.94 (3)	2.30 (3)	3.2130 (18)	163 (2)
N2—H2N···Cl1i	0.97 (2)	2.21 (2)	3.1287 (19)	158 (2)
N2—H3N···Cl1ii	0.93 (3)	2.20 (3)	3.1235 (18)	172 (2)
C8—H8A···Cg1iii	0.99	2.64	3.542 (2)	152

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C9–C14 phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N⋯Cl1	0.94 (3)	2.30 (3)	3.2130 (18)	163 (2)
N2—H2N⋯Cl1i	0.97 (2)	2.21 (2)	3.1287 (19)	158 (2)
N2—H3N⋯Cl1ii	0.93 (3)	2.20 (3)	3.1235 (18)	172 (2)
C8—H8A⋯Cg1iii	0.99	2.64	3.542 (2)	152

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