2-Chloro-anilinium perchlorate.

In the crystal of the title compound, C(6)H(7)ClN(+)·ClO(4) (-), a layer-like structure parallel to the bc plane is formed through N-H⋯O hydrogen bonds between the cations and anions. These layers are connected by weak C-H⋯O inter-actions, forming a three-dimensional network.

Related literature

For general background to ferroelectric organic frameworks, see: Gray et al. (2002 ▶); Fu et al. (2007 ▶); Ye et al. (2009 ▶). For phase transitions of ferroelectric materials, see: Ye et al. (2006 ▶); Zhang et al. (2008 ▶); Zhao et al. (2008 ▶). For related structures, see: Gray et al. (2002 ▶); Balamurugan et al. (2010 ▶).

Experimental

Crystal data

C6H7ClN+·n class="Chemical">ClO4 −

M = 228.03

Monoclinic,

a = 11.069 (2) Å

b = 7.3093 (15) Å

c = 13.718 (5) Å

β = 125.737 (19)°

V = 900.9 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.70 mm−1

T = 293 K

0.20 × 0.20 × 0.20 mm

Data collection

Rigaku SCXmini diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.869, T max = 0.869

8912 measured reflections

2060 independent reflections

1749 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.089

S = 2.26

2060 reflections

119 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.38 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536812023963/zq2165sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812023963/zq2165Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812023963/zq2165Isup3.cml

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

C6H7ClN+·ClO4−	F(000) = 464
Mr = 228.03	Dx = 1.681 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2060 reflections
a = 11.069 (2) Å	θ = 3.3–27.5°
b = 7.3093 (15) Å	µ = 0.70 mm−1
c = 13.718 (5) Å	T = 293 K
β = 125.737 (19)°	Prism, colourless
V = 900.9 (4) Å3	0.20 × 0.20 × 0.20 mm
Z = 4

Rigaku SCXmini diffractometer	2060 independent reflections
Radiation source: fine-focus sealed tube	1749 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.040
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 3.3°
CCD_Profile_fitting scans	h = −14→14
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −9→9
Tmin = 0.869, Tmax = 0.869	l = −17→17
8912 measured 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)] = 0.046	H-atom parameters constrained
wR(F2) = 0.089	w = 1/[σ2(Fo2) + (0.010P)2] where P = (Fo2 + 2Fc2)/3
S = 2.26	(Δ/σ)max < 0.001
2060 reflections	Δρmax = 0.31 e Å−3
119 parameters	Δρmin = −0.38 e Å−3
0 restraints	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.231 (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. 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
Cl2	−0.30288 (8)	−0.34063 (9)	−0.34203 (6)	0.0620 (3)
N1	−0.12505 (19)	−0.1679 (2)	−0.41599 (16)	0.0359 (5)
H1A	−0.0953	−0.0767	−0.3637	0.043*
H1B	−0.0808	−0.1583	−0.4530	0.043*
H1C	−0.1008	−0.2743	−0.3773	0.043*
C1	−0.2866 (2)	−0.1583 (3)	−0.50492 (19)	0.0316 (5)
C2	−0.3452 (3)	−0.0700 (3)	−0.6122 (2)	0.0421 (6)
H2	−0.2824	−0.0175	−0.6287	0.051*
C3	−0.4974 (3)	−0.0596 (3)	−0.6954 (2)	0.0556 (7)
H3	−0.5375	−0.0005	−0.7683	0.067*
C4	−0.5902 (3)	−0.1370 (3)	−0.6702 (3)	0.0584 (8)
H4	−0.6928	−0.1305	−0.7267	0.070*
C5	−0.5324 (3)	−0.2237 (3)	−0.5624 (3)	0.0536 (7)
H5	−0.5954	−0.2742	−0.5455	0.064*
C6	−0.3789 (3)	−0.2350 (3)	−0.4790 (2)	0.0391 (5)
Cl1	0.07943 (6)	−0.17797 (7)	−0.07815 (5)	0.0349 (2)
O1	0.21439 (19)	−0.0998 (3)	0.01753 (15)	0.0676 (6)
O2	0.10292 (19)	−0.2780 (2)	−0.15577 (14)	0.0545 (5)
O3	0.0235 (2)	−0.3048 (2)	−0.03403 (16)	0.0582 (5)
O4	−0.0262 (2)	−0.0368 (2)	−0.14591 (16)	0.0658 (5)

	U11	U22	U33	U12	U13	U23
Cl2	0.0771 (6)	0.0615 (5)	0.0639 (5)	−0.0132 (3)	0.0506 (5)	0.0054 (3)
N1	0.0367 (11)	0.0319 (10)	0.0425 (11)	−0.0002 (8)	0.0251 (10)	0.0026 (8)
C1	0.0303 (12)	0.0283 (12)	0.0360 (12)	−0.0023 (8)	0.0192 (11)	−0.0060 (9)
C2	0.0420 (14)	0.0435 (14)	0.0394 (13)	−0.0055 (10)	0.0229 (12)	−0.0035 (10)
C3	0.0513 (17)	0.0539 (17)	0.0420 (14)	0.0032 (12)	0.0163 (14)	−0.0065 (12)
C4	0.0341 (15)	0.0604 (18)	0.0604 (19)	−0.0024 (12)	0.0161 (14)	−0.0211 (14)
C5	0.0423 (16)	0.0518 (16)	0.0750 (19)	−0.0159 (12)	0.0389 (15)	−0.0235 (14)
C6	0.0457 (15)	0.0315 (12)	0.0499 (14)	−0.0057 (10)	0.0335 (13)	−0.0077 (10)
Cl1	0.0385 (3)	0.0308 (3)	0.0353 (3)	−0.0012 (2)	0.0214 (3)	0.0015 (2)
O1	0.0539 (12)	0.0806 (13)	0.0458 (10)	−0.0245 (10)	0.0163 (10)	−0.0160 (9)
O2	0.0699 (13)	0.0548 (11)	0.0535 (11)	0.0007 (9)	0.0443 (11)	−0.0075 (8)
O3	0.0762 (13)	0.0476 (11)	0.0782 (13)	−0.0014 (8)	0.0606 (12)	0.0120 (9)
O4	0.0618 (12)	0.0375 (10)	0.0780 (13)	0.0180 (8)	0.0294 (11)	0.0155 (9)

Cl2—C6	1.729 (2)	C3—H3	0.9300
N1—C1	1.464 (3)	C4—C5	1.376 (4)
N1—H1A	0.8900	C4—H4	0.9300
N1—H1B	0.8899	C5—C6	1.390 (3)
N1—H1C	0.8900	C5—H5	0.9300
C1—C2	1.374 (3)	Cl1—O1	1.4107 (17)
C1—C6	1.381 (3)	Cl1—O4	1.4237 (16)
C2—C3	1.379 (3)	Cl1—O3	1.4309 (15)
C2—H2	0.9300	Cl1—O2	1.4350 (16)
C3—C4	1.382 (4)
C1—N1—H1A	109.4	C5—C4—C3	120.7 (2)
C1—N1—H1B	109.4	C5—C4—H4	119.6
H1A—N1—H1B	109.5	C3—C4—H4	119.6
C1—N1—H1C	109.6	C4—C5—C6	119.3 (2)
H1A—N1—H1C	109.5	C4—C5—H5	120.4
H1B—N1—H1C	109.5	C6—C5—H5	120.4
C2—C1—C6	120.6 (2)	C1—C6—C5	119.8 (2)
C2—C1—N1	119.84 (19)	C1—C6—Cl2	119.82 (18)
C6—C1—N1	119.5 (2)	C5—C6—Cl2	120.40 (19)
C1—C2—C3	119.8 (2)	O1—Cl1—O4	109.51 (12)
C1—C2—H2	120.1	O1—Cl1—O3	110.70 (11)
C3—C2—H2	120.1	O4—Cl1—O3	110.62 (11)
C2—C3—C4	119.9 (2)	O1—Cl1—O2	110.14 (11)
C2—C3—H3	120.1	O4—Cl1—O2	108.70 (11)
C4—C3—H3	120.1	O3—Cl1—O2	107.13 (11)
C6—C1—C2—C3	−0.7 (3)	N1—C1—C6—C5	179.00 (19)
N1—C1—C2—C3	−179.39 (19)	C2—C1—C6—Cl2	−178.46 (16)
C1—C2—C3—C4	0.3 (3)	N1—C1—C6—Cl2	0.2 (3)
C2—C3—C4—C5	0.4 (4)	C4—C5—C6—C1	0.5 (3)
C3—C4—C5—C6	−0.8 (4)	C4—C5—C6—Cl2	179.23 (18)
C2—C1—C6—C5	0.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2i	0.89	2.21	2.978 (2)	145
N1—H1A···O4	0.89	2.63	3.333 (3)	136
N1—H1B···O3ii	0.89	2.04	2.911 (2)	168
N1—H1C···O4iii	0.89	2.29	3.022 (2)	140
N1—H1C···O2	0.89	2.51	3.039 (3)	118
C3—H3···O1iv	0.93	2.70	3.331 (3)	126

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2i	0.89	2.21	2.978 (2)	145
N1—H1A⋯O4	0.89	2.63	3.333 (3)	136
N1—H1B⋯O3ii	0.89	2.04	2.911 (2)	168
N1—H1C⋯O4iii	0.89	2.29	3.022 (2)	140
N1—H1C⋯O2	0.89	2.51	3.039 (3)	118
C3—H3⋯O1iv	0.93	2.70	3.331 (3)	126

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