Cyclo-hexa-naminium 3,4,5,6-tetra-chloro-2-(meth-oxy-carbon-yl)benzoate.

In the title compound, C(6)H(14)N(+)·C(9)H(3)Cl(4)O(4) (-), the cyclo-hexane ring of the cation adopts a chair conformation. In the anion, the mean planes of the meth-oxy-carbonyl and carboxyl-ate groups form dihedral angles of 67.3 (3) and 55.7 (3)°, respectively, with the benzene ring. In the crystal, inter-molecular N-H⋯O hydrogen bonds connect the components into chains along [100].

Related literature

For related structures, see: Li (2011 ▶); Liang (2008 ▶).

Experimental

Crystal data

C6H14N+·C9H3Cl4O4 −

M = 417.10

Triclinic,

a = 5.9435 (4) Å

b = 11.3494 (12) Å

c = 14.3414 (15) Å

α = 90.755 (1)°

β = 97.901 (1)°

γ = 101.651 (2)°

V = 937.64 (15) Å3

Z = 2

Mo Kα radiation

μ = 0.65 mm−1

T = 298 K

0.45 × 0.42 × 0.40 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1997 ▶) T min = 0.759, T max = 0.781

4881 measured reflections

3239 independent reflections

2041 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.136

S = 1.03

3239 reflections

219 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.32 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811008531/lh5210sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811008531/lh5210Isup2.hkl

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

C6H14N+·C9H3Cl4O4−	Z = 2
Mr = 417.10	F(000) = 428
Triclinic, P1	Dx = 1.477 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.9435 (4) Å	Cell parameters from 1650 reflections
b = 11.3494 (12) Å	θ = 2.3–24.6°
c = 14.3414 (15) Å	µ = 0.65 mm−1
α = 90.755 (1)°	T = 298 K
β = 97.901 (1)°	Block, colorless
γ = 101.651 (2)°	0.45 × 0.42 × 0.40 mm
V = 937.64 (15) Å3

Bruker SMART CCD diffractometer	3239 independent reflections
Radiation source: fine-focus sealed tube	2041 reflections with I > 2σ(I)
graphite	Rint = 0.017
φ and ω scans	θmax = 25.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −7→6
Tmin = 0.759, Tmax = 0.781	k = −9→13
4881 measured reflections	l = −16→16

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.136	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0463P)2 + 0.7109P] where P = (Fo2 + 2Fc2)/3
3239 reflections	(Δ/σ)max = 0.001
219 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.32 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	0.0817 (2)	0.80648 (10)	0.03785 (7)	0.0826 (4)
Cl2	−0.1463 (2)	0.97241 (11)	0.14937 (11)	0.1099 (5)
Cl3	−0.0240 (3)	1.00178 (11)	0.36695 (12)	0.1385 (7)
Cl4	0.3042 (3)	0.85179 (12)	0.47324 (8)	0.1157 (5)
N1	0.2196 (4)	0.5077 (3)	0.90782 (18)	0.0543 (7)
H1A	0.0689	0.4744	0.8983	0.081*
H1B	0.2651	0.5258	0.9690	0.081*
H1C	0.2996	0.4561	0.8883	0.081*
O1	0.6531 (5)	0.7188 (3)	0.40242 (19)	0.0921 (10)
O2	0.3683 (5)	0.5620 (3)	0.3543 (2)	0.0804 (8)
O3	0.5961 (4)	0.6704 (2)	0.16858 (18)	0.0648 (7)
O4	0.2495 (4)	0.5752 (2)	0.09970 (15)	0.0538 (6)
C1	0.4495 (6)	0.6663 (4)	0.3552 (2)	0.0596 (9)
C2	0.3833 (6)	0.6552 (3)	0.1529 (2)	0.0440 (7)
C3	0.3263 (6)	0.7536 (3)	0.3036 (2)	0.0521 (8)
C4	0.2755 (5)	0.7423 (3)	0.2053 (2)	0.0452 (8)
C5	0.1354 (6)	0.8134 (3)	0.1590 (2)	0.0528 (8)
C6	0.0384 (7)	0.8919 (3)	0.2082 (3)	0.0665 (11)
C7	0.0916 (8)	0.9040 (3)	0.3046 (3)	0.0759 (12)
C8	0.2351 (7)	0.8370 (3)	0.3518 (3)	0.0673 (11)
C9	0.7685 (9)	0.6398 (6)	0.4622 (4)	0.125 (2)
H9A	0.6549	0.5838	0.4896	0.188*
H9B	0.8763	0.6871	0.5113	0.188*
H9C	0.8503	0.5966	0.4251	0.188*
C10	0.2615 (6)	0.6191 (3)	0.8543 (3)	0.0621 (10)
H10	0.1572	0.6702	0.8708	0.075*
C11	0.5086 (7)	0.6870 (4)	0.8821 (3)	0.0747 (11)
H11A	0.6150	0.6355	0.8709	0.090*
H11B	0.5344	0.7096	0.9488	0.090*
C12	0.5552 (9)	0.7989 (4)	0.8256 (4)	0.1079 (17)
H12A	0.4623	0.8545	0.8431	0.130*
H12B	0.7174	0.8381	0.8409	0.130*
C13	0.4999 (10)	0.7705 (5)	0.7218 (4)	0.121 (2)
H13A	0.6065	0.7235	0.7028	0.145*
H13B	0.5208	0.8449	0.6885	0.145*
C14	0.2526 (10)	0.7006 (5)	0.6948 (4)	0.1153 (19)
H14A	0.1452	0.7514	0.7063	0.138*
H14B	0.2261	0.6781	0.6281	0.138*
C15	0.2075 (8)	0.5892 (4)	0.7506 (3)	0.0829 (13)
H15A	0.0459	0.5491	0.7351	0.100*
H15B	0.3023	0.5343	0.7336	0.100*

	U11	U22	U33	U12	U13	U23
Cl1	0.0978 (8)	0.0969 (8)	0.0616 (6)	0.0438 (7)	0.0045 (5)	0.0168 (5)
Cl2	0.1097 (10)	0.0726 (7)	0.1708 (13)	0.0512 (7)	0.0501 (9)	0.0356 (8)
Cl3	0.2122 (17)	0.0708 (8)	0.1644 (14)	0.0421 (9)	0.1197 (13)	−0.0101 (8)
Cl4	0.1700 (14)	0.1050 (9)	0.0601 (7)	−0.0151 (9)	0.0422 (8)	−0.0307 (6)
N1	0.0421 (16)	0.0685 (19)	0.0515 (16)	0.0113 (14)	0.0050 (13)	−0.0072 (14)
O1	0.0748 (19)	0.109 (2)	0.0676 (18)	−0.0237 (17)	−0.0154 (15)	0.0083 (17)
O2	0.0749 (19)	0.0667 (18)	0.085 (2)	−0.0021 (15)	−0.0154 (15)	0.0157 (15)
O3	0.0399 (14)	0.0735 (17)	0.0796 (17)	0.0094 (12)	0.0088 (12)	−0.0134 (13)
O4	0.0450 (13)	0.0612 (14)	0.0530 (13)	0.0098 (11)	0.0028 (11)	−0.0159 (11)
C1	0.060 (2)	0.070 (3)	0.0400 (19)	−0.005 (2)	0.0039 (17)	0.0014 (18)
C2	0.047 (2)	0.0497 (19)	0.0373 (17)	0.0120 (16)	0.0086 (15)	0.0040 (15)
C3	0.057 (2)	0.0472 (19)	0.0468 (19)	−0.0069 (16)	0.0145 (16)	−0.0050 (15)
C4	0.0432 (18)	0.0445 (18)	0.0466 (18)	0.0042 (15)	0.0092 (14)	−0.0022 (14)
C5	0.055 (2)	0.050 (2)	0.055 (2)	0.0082 (17)	0.0171 (17)	0.0047 (16)
C6	0.073 (3)	0.041 (2)	0.094 (3)	0.0166 (18)	0.037 (2)	0.012 (2)
C7	0.101 (3)	0.045 (2)	0.090 (3)	0.010 (2)	0.054 (3)	−0.006 (2)
C8	0.090 (3)	0.053 (2)	0.056 (2)	−0.008 (2)	0.033 (2)	−0.0106 (18)
C9	0.085 (4)	0.173 (6)	0.091 (4)	−0.006 (4)	−0.035 (3)	0.038 (4)
C10	0.053 (2)	0.066 (2)	0.067 (2)	0.0155 (19)	0.0009 (18)	−0.0006 (19)
C11	0.061 (3)	0.071 (3)	0.083 (3)	0.004 (2)	−0.008 (2)	0.007 (2)
C12	0.093 (4)	0.084 (3)	0.129 (5)	−0.006 (3)	−0.013 (3)	0.026 (3)
C13	0.115 (5)	0.116 (4)	0.117 (5)	−0.006 (4)	0.002 (4)	0.053 (4)
C14	0.117 (4)	0.121 (4)	0.091 (4)	0.006 (4)	−0.021 (3)	0.038 (3)
C15	0.077 (3)	0.091 (3)	0.069 (3)	0.003 (2)	−0.011 (2)	0.010 (2)

Cl1—C5	1.721 (3)	C9—H9A	0.9600
Cl2—C6	1.710 (4)	C9—H9B	0.9600
Cl3—C7	1.718 (4)	C9—H9C	0.9600
Cl4—C8	1.732 (4)	C10—C15	1.497 (5)
N1—C10	1.483 (4)	C10—C11	1.511 (5)
N1—H1A	0.8900	C10—H10	0.9800
N1—H1B	0.8900	C11—C12	1.514 (6)
N1—H1C	0.8900	C11—H11A	0.9700
O1—C1	1.323 (4)	C11—H11B	0.9700
O1—C9	1.454 (5)	C12—C13	1.496 (7)
O2—C1	1.185 (4)	C12—H12A	0.9700
O3—C2	1.230 (4)	C12—H12B	0.9700
O4—C2	1.250 (4)	C13—C14	1.518 (7)
C1—C3	1.492 (5)	C13—H13A	0.9700
C2—C4	1.523 (4)	C13—H13B	0.9700
C3—C4	1.399 (4)	C14—C15	1.503 (6)
C3—C8	1.400 (5)	C14—H14A	0.9700
C4—C5	1.386 (4)	C14—H14B	0.9700
C5—C6	1.388 (5)	C15—H15A	0.9700
C6—C7	1.374 (6)	C15—H15B	0.9700
C7—C8	1.371 (6)
C10—N1—H1A	109.5	N1—C10—C15	110.3 (3)
C10—N1—H1B	109.5	N1—C10—C11	109.9 (3)
H1A—N1—H1B	109.5	C15—C10—C11	111.8 (3)
C10—N1—H1C	109.5	N1—C10—H10	108.2
H1A—N1—H1C	109.5	C15—C10—H10	108.2
H1B—N1—H1C	109.5	C11—C10—H10	108.2
C1—O1—C9	114.8 (3)	C10—C11—C12	110.3 (3)
O2—C1—O1	124.7 (4)	C10—C11—H11A	109.6
O2—C1—C3	122.5 (3)	C12—C11—H11A	109.6
O1—C1—C3	112.7 (3)	C10—C11—H11B	109.6
O3—C2—O4	126.4 (3)	C12—C11—H11B	109.6
O3—C2—C4	115.8 (3)	H11A—C11—H11B	108.1
O4—C2—C4	117.8 (3)	C13—C12—C11	112.0 (4)
C4—C3—C8	118.9 (3)	C13—C12—H12A	109.2
C4—C3—C1	119.3 (3)	C11—C12—H12A	109.2
C8—C3—C1	121.3 (3)	C13—C12—H12B	109.2
C5—C4—C3	118.9 (3)	C11—C12—H12B	109.2
C5—C4—C2	122.4 (3)	H12A—C12—H12B	107.9
C3—C4—C2	118.7 (3)	C12—C13—C14	111.5 (5)
C4—C5—C6	121.4 (3)	C12—C13—H13A	109.3
C4—C5—Cl1	119.8 (2)	C14—C13—H13A	109.3
C6—C5—Cl1	118.8 (3)	C12—C13—H13B	109.3
C7—C6—C5	119.4 (4)	C14—C13—H13B	109.3
C7—C6—Cl2	120.3 (3)	H13A—C13—H13B	108.0
C5—C6—Cl2	120.3 (3)	C15—C14—C13	111.0 (4)
C8—C7—C6	120.2 (3)	C15—C14—H14A	109.4
C8—C7—Cl3	119.6 (3)	C13—C14—H14A	109.4
C6—C7—Cl3	120.3 (4)	C15—C14—H14B	109.4
C7—C8—C3	121.2 (3)	C13—C14—H14B	109.4
C7—C8—Cl4	120.6 (3)	H14A—C14—H14B	108.0
C3—C8—Cl4	118.2 (3)	C10—C15—C14	111.3 (4)
O1—C9—H9A	109.5	C10—C15—H15A	109.4
O1—C9—H9B	109.5	C14—C15—H15A	109.4
H9A—C9—H9B	109.5	C10—C15—H15B	109.4
O1—C9—H9C	109.5	C14—C15—H15B	109.4
H9A—C9—H9C	109.5	H15A—C15—H15B	108.0
H9B—C9—H9C	109.5
C9—O1—C1—O2	−5.2 (6)	Cl1—C5—C6—Cl2	4.3 (4)
C9—O1—C1—C3	173.5 (4)	C5—C6—C7—C8	−1.5 (6)
O2—C1—C3—C4	−63.1 (5)	Cl2—C6—C7—C8	178.3 (3)
O1—C1—C3—C4	118.2 (3)	C5—C6—C7—Cl3	179.4 (3)
O2—C1—C3—C8	108.9 (4)	Cl2—C6—C7—Cl3	−0.9 (5)
O1—C1—C3—C8	−69.8 (4)	C6—C7—C8—C3	−1.3 (6)
C8—C3—C4—C5	−0.5 (5)	Cl3—C7—C8—C3	177.9 (3)
C1—C3—C4—C5	171.7 (3)	C6—C7—C8—Cl4	179.8 (3)
C8—C3—C4—C2	177.4 (3)	Cl3—C7—C8—Cl4	−1.0 (5)
C1—C3—C4—C2	−10.4 (4)	C4—C3—C8—C7	2.3 (5)
O3—C2—C4—C5	122.9 (3)	C1—C3—C8—C7	−169.7 (3)
O4—C2—C4—C5	−58.1 (4)	C4—C3—C8—Cl4	−178.8 (2)
O3—C2—C4—C3	−54.9 (4)	C1—C3—C8—Cl4	9.1 (5)
O4—C2—C4—C3	124.1 (3)	N1—C10—C11—C12	178.3 (4)
C3—C4—C5—C6	−2.3 (5)	C15—C10—C11—C12	55.4 (5)
C2—C4—C5—C6	179.8 (3)	C10—C11—C12—C13	−54.7 (6)
C3—C4—C5—Cl1	176.9 (2)	C11—C12—C13—C14	54.7 (6)
C2—C4—C5—Cl1	−1.0 (4)	C12—C13—C14—C15	−54.6 (7)
C4—C5—C6—C7	3.3 (5)	N1—C10—C15—C14	−179.0 (4)
Cl1—C5—C6—C7	−175.9 (3)	C11—C10—C15—C14	−56.4 (5)
C4—C5—C6—Cl2	−176.5 (3)	C13—C14—C15—C10	55.3 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O4i	0.89	1.87	2.743 (4)	168
N1—H1B···O4ii	0.89	1.97	2.819 (3)	159
N1—H1C···O3iii	0.89	1.89	2.766 (4)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O4i	0.89	1.87	2.743 (4)	168
N1—H1B⋯O4ii	0.89	1.97	2.819 (3)	159
N1—H1C⋯O3iii	0.89	1.89	2.766 (4)	167

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