4-Chloro-anilinium thio-cyanate.

In the title compound, C(6)H(7)ClN(+)·NCS(-), the benzene ring and the protonated amine and chloro substituents are nearly planar, with a maximum deviation of 0.002 (2) Å for the N atom. In the crystal, the mol-ecules are linked by N-H⋯N and N-H⋯S hydrogen bonds into a chain along the b axis.

Related literature

For bond-length data see: Allen et al. (1987 ▶) and for a description of the Cambridge Structural Database, see: Allen (2002 ▶). For related thio­cyanate structures, see: Salem et al. (2012 ▶); Selvakumaran et al. (2011 ▶); Khawar Rauf et al. (2008 ▶).

Experimental

Crystal data

C6H7ClN+·NCS−

M = 186.66

Orthorhombic,

a = 7.743 (2) Å

b = 7.199 (2) Å

c = 31.913 (10) Å

V = 1778.8 (10) Å3

Z = 8

Mo Kα radiation

μ = 0.60 mm−1

T = 298 K

0.50 × 0.43 × 0.30 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.754, T max = 0.841

10422 measured reflections

1846 independent reflections

1628 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.108

S = 1.18

1846 reflections

112 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.31 e Å−3

Δρmin = −0.19 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681202377X/bq2362sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681202377X/bq2362Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681202377X/bq2362Isup3.cml

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

C6H7ClN+·NCS−	F(000) = 768
Mr = 186.66	Dx = 1.394 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 4443 reflections
a = 7.743 (2) Å	θ = 1.2–26.5°
b = 7.199 (2) Å	µ = 0.60 mm−1
c = 31.913 (10) Å	T = 298 K
V = 1778.8 (10) Å3	Slab, colourless
Z = 8	0.50 × 0.43 × 0.30 mm

Bruker SMART APEX CCD area-detector diffractometer	1846 independent reflections
Radiation source: fine-focus sealed tube	1628 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
Detector resolution: 83.66 pixels mm-1	θmax = 26.5°, θmin = 1.2°
ω scan	h = −5→9
Absorption correction: multi-scan (SADABS; Bruker, 2000)	k = −9→8
Tmin = 0.754, Tmax = 0.841	l = −38→40
10422 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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108	H atoms treated by a mixture of independent and constrained refinement
S = 1.18	w = 1/[σ2(Fo2) + (0.0501P)2 + 0.6879P] where P = (Fo2 + 2Fc2)/3
1846 reflections	(Δ/σ)max < 0.002
112 parameters	Δρmax = 0.31 e Å−3
3 restraints	Δρmin = −0.19 e Å−3

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.

	x	y	z	Uiso*/Ueq
Cl1	0.41886 (10)	0.01916 (11)	0.749321 (18)	0.0681 (2)
S1	0.66687 (7)	0.20120 (7)	0.468838 (17)	0.04316 (18)
N1	0.5614 (2)	0.1442 (3)	0.56935 (6)	0.0404 (4)
H1A	0.6668 (16)	0.111 (4)	0.5642 (7)	0.048 (7)*
H1B	0.550 (3)	0.2589 (17)	0.5623 (8)	0.062 (8)*
H1C	0.490 (3)	0.082 (4)	0.5539 (7)	0.068 (8)*
N2	0.4214 (2)	0.4537 (3)	0.43930 (7)	0.0510 (5)
C1	0.4128 (3)	0.2283 (4)	0.63414 (7)	0.0581 (6)
H1	0.3576	0.3241	0.6199	0.070*
C2	0.3805 (4)	0.1992 (4)	0.67630 (8)	0.0638 (7)
H2	0.3038	0.2757	0.6906	0.077*
C3	0.4620 (3)	0.0576 (3)	0.69664 (6)	0.0446 (5)
C4	0.5754 (3)	−0.0562 (3)	0.67624 (7)	0.0561 (6)
H4	0.6301	−0.1524	0.6904	0.067*
C5	0.6076 (3)	−0.0262 (3)	0.63414 (7)	0.0526 (6)
H5	0.6847	−0.1023	0.6198	0.063*
C6	0.5263 (2)	0.1152 (3)	0.61366 (6)	0.0363 (4)
C7	0.5235 (3)	0.3494 (3)	0.45172 (6)	0.0367 (4)

	U11	U22	U33	U12	U13	U23
Cl1	0.0875 (5)	0.0781 (5)	0.0387 (3)	−0.0028 (4)	0.0118 (3)	0.0012 (3)
S1	0.0390 (3)	0.0415 (3)	0.0490 (3)	0.0027 (2)	0.0001 (2)	0.0058 (2)
N1	0.0408 (10)	0.0419 (10)	0.0387 (9)	−0.0012 (8)	−0.0013 (8)	0.0028 (7)
N2	0.0441 (10)	0.0450 (10)	0.0639 (12)	0.0019 (9)	−0.0057 (9)	0.0067 (9)
C1	0.0664 (16)	0.0605 (14)	0.0473 (13)	0.0269 (13)	−0.0001 (11)	0.0027 (11)
C2	0.0710 (16)	0.0712 (16)	0.0491 (13)	0.0305 (14)	0.0105 (12)	−0.0039 (12)
C3	0.0497 (12)	0.0505 (12)	0.0338 (9)	−0.0063 (10)	0.0016 (9)	−0.0028 (9)
C4	0.0690 (16)	0.0528 (13)	0.0465 (12)	0.0168 (12)	0.0043 (11)	0.0104 (10)
C5	0.0606 (14)	0.0531 (13)	0.0440 (12)	0.0189 (11)	0.0098 (10)	0.0047 (10)
C6	0.0354 (9)	0.0366 (10)	0.0368 (10)	−0.0023 (8)	−0.0018 (8)	−0.0012 (7)
C7	0.0372 (10)	0.0338 (9)	0.0392 (10)	−0.0066 (8)	0.0024 (8)	−0.0005 (8)

Cl1—C3	1.736 (2)	C1—H1	0.9300
S1—C7	1.634 (2)	C2—C3	1.363 (3)
N1—C6	1.455 (3)	C2—H2	0.9300
N1—H1A	0.866 (10)	C3—C4	1.365 (3)
N1—H1B	0.860 (10)	C4—C5	1.384 (3)
N1—H1C	0.868 (10)	C4—H4	0.9300
N2—C7	1.160 (3)	C5—C6	1.364 (3)
C1—C6	1.365 (3)	C5—H5	0.9300
C1—C2	1.385 (4)
C6—N1—H1A	108.8 (16)	C2—C3—Cl1	119.39 (18)
C6—N1—H1B	111.9 (19)	C4—C3—Cl1	119.33 (18)
H1A—N1—H1B	108 (3)	C3—C4—C5	119.0 (2)
C6—N1—H1C	110.9 (19)	C3—C4—H4	120.5
H1A—N1—H1C	111 (3)	C5—C4—H4	120.5
H1B—N1—H1C	107 (3)	C6—C5—C4	119.9 (2)
C6—C1—C2	119.4 (2)	C6—C5—H5	120.1
C6—C1—H1	120.3	C4—C5—H5	120.1
C2—C1—H1	120.3	C5—C6—C1	120.9 (2)
C3—C2—C1	119.5 (2)	C5—C6—N1	119.10 (18)
C3—C2—H2	120.3	C1—C6—N1	120.02 (19)
C1—C2—H2	120.3	N2—C7—S1	179.5 (2)
C2—C3—C4	121.3 (2)
C6—C1—C2—C3	−0.3 (4)	C3—C4—C5—C6	−0.1 (4)
C1—C2—C3—C4	0.2 (4)	C4—C5—C6—C1	0.0 (4)
C1—C2—C3—Cl1	−179.0 (2)	C4—C5—C6—N1	−179.8 (2)
C2—C3—C4—C5	0.1 (4)	C2—C1—C6—C5	0.2 (4)
Cl1—C3—C4—C5	179.2 (2)	C2—C1—C6—N1	180.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N2i	0.87 (2)	2.03 (1)	2.888 (2)	172 (2)
N1—H1B···N2ii	0.86 (1)	2.08 (1)	2.911 (3)	162 (2)
N1—H1C···S1iii	0.87 (2)	2.48 (3)	3.285 (2)	155 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯N2i	0.87 (2)	2.03 (1)	2.888 (2)	172 (2)
N1—H1B⋯N2ii	0.86 (1)	2.08 (1)	2.911 (3)	162 (2)
N1—H1C⋯S1iii	0.87 (2)	2.48 (3)	3.285 (2)	155 (2)

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