Hexane-1,6-diaminium bis-[3,4,5,6-tetra-chloro-2-(meth-oxy-carbon-yl)benzoate].

In the anion of the title salt, C(6)H(18)N(2) (2+)·2C(9)H(3)Cl(4)O(4) (-), the meth-oxy-carbonyl and carboxyl groups are aligned at dihedral angles of 71.0 (3) and 100.9 (3)°, respectively, with the aromatic ring. The asymmetric unit contains half a cation and one anion. In the crystal, inter-molecular N-H⋯O, C-H⋯Cl and C-H⋯O hydrogen bonds link the components into a three-dimensional network.

Related literature

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

Experimental

Crystal data

C6H18N2 2+·2C9H3Cl4O4 −

M = 752.05

Monoclinic,

a = 31.236 (3) Å

b = 5.8911 (4) Å

c = 18.3762 (18) Å

β = 107.118 (1)°

V = 3231.7 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.74 mm−1

T = 298 K

0.37 × 0.28 × 0.15 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1997 ▶) T min = 0.770, T max = 0.897

7618 measured reflections

2829 independent reflections

1817 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.154

S = 1.04

2829 reflections

192 parameters

H-atom parameters constrained

Δρmax = 0.51 e Å−3

Δρmin = −0.41 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/S1600536811008506/bt5475sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811008506/bt5475Isup2.hkl

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

C6H18N22+·2C9H3Cl4O4−	F(000) = 1528
Mr = 752.05	Dx = 1.546 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 31.236 (3) Å	Cell parameters from 2053 reflections
b = 5.8911 (4) Å	θ = 2.7–26.1°
c = 18.3762 (18) Å	µ = 0.74 mm−1
β = 107.118 (1)°	T = 298 K
V = 3231.7 (5) Å3	Block, colorless
Z = 4	0.37 × 0.28 × 0.15 mm

Bruker SMART CCD diffractometer	2829 independent reflections
Radiation source: fine-focus sealed tube	1817 reflections with I > 2σ(I)
graphite	Rint = 0.037
φ and ω scans	θmax = 25.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −36→29
Tmin = 0.770, Tmax = 0.897	k = −6→7
7618 measured reflections	l = −21→21

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.154	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0489P)2 + 12.9951P] where P = (Fo2 + 2Fc2)/3
2829 reflections	(Δ/σ)max < 0.001
192 parameters	Δρmax = 0.51 e Å−3
0 restraints	Δρmin = −0.41 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	0.16469 (4)	0.8320 (3)	0.02548 (7)	0.0738 (5)
Cl2	0.10240 (5)	0.4349 (3)	−0.04960 (8)	0.0845 (5)
Cl3	0.03378 (5)	0.2434 (2)	0.02771 (10)	0.0912 (6)
Cl4	0.02472 (5)	0.4714 (3)	0.17526 (10)	0.0918 (6)
N1	0.21033 (11)	0.4754 (6)	0.26915 (19)	0.0485 (9)
H1A	0.2012	0.6131	0.2512	0.073*
H1B	0.1918	0.3715	0.2417	0.073*
H1C	0.2379	0.4510	0.2662	0.073*
O1	0.06089 (14)	0.9497 (7)	0.2473 (2)	0.0906 (13)
O2	0.12386 (14)	0.7821 (10)	0.3033 (2)	0.1124 (18)
O3	0.14859 (11)	1.1892 (6)	0.1748 (2)	0.0769 (12)
O4	0.19786 (10)	0.9160 (5)	0.21430 (17)	0.0537 (8)
C1	0.09506 (15)	0.8248 (9)	0.2481 (3)	0.0558 (12)
C2	0.16017 (13)	0.9909 (7)	0.1788 (2)	0.0400 (10)
C3	0.09403 (13)	0.7360 (7)	0.1712 (2)	0.0432 (10)
C4	0.12605 (12)	0.8139 (6)	0.1380 (2)	0.0373 (9)
C5	0.12705 (13)	0.7243 (7)	0.0688 (2)	0.0458 (10)
C6	0.09835 (14)	0.5502 (7)	0.0339 (3)	0.0511 (12)
C7	0.06762 (15)	0.4685 (8)	0.0678 (3)	0.0559 (13)
C8	0.06449 (14)	0.5651 (8)	0.1346 (3)	0.0542 (12)
C9	0.0599 (3)	1.0419 (13)	0.3203 (3)	0.122 (3)
H9A	0.0605	0.9197	0.3552	0.184*
H9B	0.0330	1.1290	0.3134	0.184*
H9C	0.0855	1.1377	0.3405	0.184*
C10	0.21042 (15)	0.4596 (8)	0.3498 (3)	0.0531 (12)
H10A	0.2253	0.3210	0.3722	0.064*
H10B	0.1798	0.4547	0.3523	0.064*
C11	0.23434 (15)	0.6622 (8)	0.3940 (2)	0.0498 (11)
H11A	0.2645	0.6693	0.3894	0.060*
H11B	0.2188	0.7997	0.3718	0.060*
C12	0.23681 (14)	0.6522 (8)	0.4771 (2)	0.0517 (11)
H12A	0.2507	0.5102	0.4983	0.062*
H12B	0.2066	0.6541	0.4816	0.062*

	U11	U22	U33	U12	U13	U23
Cl1	0.0691 (9)	0.0891 (11)	0.0710 (8)	−0.0250 (7)	0.0329 (7)	−0.0234 (7)
Cl2	0.0825 (10)	0.0811 (11)	0.0783 (9)	−0.0055 (8)	0.0057 (8)	−0.0407 (8)
Cl3	0.0688 (9)	0.0500 (8)	0.1278 (13)	−0.0243 (7)	−0.0131 (9)	−0.0073 (8)
Cl4	0.0664 (9)	0.0909 (12)	0.1210 (13)	−0.0240 (8)	0.0322 (9)	0.0288 (10)
N1	0.044 (2)	0.033 (2)	0.060 (2)	0.0003 (16)	0.0021 (17)	−0.0084 (17)
O1	0.112 (3)	0.090 (3)	0.067 (2)	0.053 (3)	0.021 (2)	0.007 (2)
O2	0.094 (3)	0.181 (5)	0.058 (2)	0.071 (3)	0.016 (2)	0.010 (3)
O3	0.063 (2)	0.035 (2)	0.105 (3)	0.0031 (16)	−0.019 (2)	−0.0100 (18)
O4	0.0404 (17)	0.0431 (18)	0.0658 (19)	−0.0031 (14)	−0.0025 (15)	0.0026 (15)
C1	0.041 (3)	0.066 (3)	0.061 (3)	0.012 (2)	0.015 (2)	0.018 (3)
C2	0.038 (2)	0.035 (3)	0.043 (2)	−0.0057 (19)	0.0049 (18)	−0.0034 (19)
C3	0.034 (2)	0.037 (2)	0.054 (3)	0.0065 (19)	0.0067 (19)	0.010 (2)
C4	0.031 (2)	0.027 (2)	0.047 (2)	0.0021 (16)	0.0018 (17)	−0.0004 (18)
C5	0.037 (2)	0.041 (3)	0.055 (3)	−0.0035 (19)	0.007 (2)	−0.008 (2)
C6	0.041 (2)	0.036 (3)	0.065 (3)	0.002 (2)	−0.002 (2)	−0.011 (2)
C7	0.040 (3)	0.036 (3)	0.075 (3)	−0.004 (2)	−0.008 (2)	−0.003 (2)
C8	0.035 (2)	0.045 (3)	0.076 (3)	−0.003 (2)	0.007 (2)	0.019 (3)
C9	0.171 (7)	0.127 (6)	0.072 (4)	0.084 (6)	0.042 (4)	0.010 (4)
C10	0.048 (3)	0.046 (3)	0.063 (3)	−0.001 (2)	0.012 (2)	−0.003 (2)
C11	0.049 (3)	0.042 (3)	0.053 (3)	0.002 (2)	0.007 (2)	−0.007 (2)
C12	0.045 (3)	0.052 (3)	0.057 (3)	0.001 (2)	0.014 (2)	−0.007 (2)

Cl1—C5	1.723 (5)	C4—C5	1.386 (6)
Cl2—C6	1.716 (5)	C5—C6	1.389 (6)
Cl3—C7	1.721 (4)	C6—C7	1.376 (7)
Cl4—C8	1.719 (5)	C7—C8	1.382 (7)
N1—C10	1.484 (5)	C9—H9A	0.9600
N1—H1A	0.8900	C9—H9B	0.9600
N1—H1B	0.8900	C9—H9C	0.9600
N1—H1C	0.8900	C10—C11	1.511 (6)
O1—C1	1.293 (5)	C10—H10A	0.9700
O1—C9	1.456 (7)	C10—H10B	0.9700
O2—C1	1.168 (5)	C11—C12	1.507 (6)
O3—C2	1.218 (5)	C11—H11A	0.9700
O4—C2	1.247 (5)	C11—H11B	0.9700
C1—C3	1.499 (6)	C12—C12i	1.519 (9)
C2—C4	1.521 (5)	C12—H12A	0.9700
C3—C4	1.394 (6)	C12—H12B	0.9700
C3—C8	1.397 (6)
C10—N1—H1A	109.5	C7—C8—C3	121.0 (4)
C10—N1—H1B	109.5	C7—C8—Cl4	120.2 (4)
H1A—N1—H1B	109.5	C3—C8—Cl4	118.8 (4)
C10—N1—H1C	109.5	O1—C9—H9A	109.5
H1A—N1—H1C	109.5	O1—C9—H9B	109.5
H1B—N1—H1C	109.5	H9A—C9—H9B	109.5
C1—O1—C9	116.3 (4)	O1—C9—H9C	109.5
O2—C1—O1	123.7 (5)	H9A—C9—H9C	109.5
O2—C1—C3	122.7 (4)	H9B—C9—H9C	109.5
O1—C1—C3	113.6 (4)	N1—C10—C11	110.0 (4)
O3—C2—O4	126.1 (4)	N1—C10—H10A	109.7
O3—C2—C4	118.3 (4)	C11—C10—H10A	109.7
O4—C2—C4	115.6 (4)	N1—C10—H10B	109.7
C4—C3—C8	119.0 (4)	C11—C10—H10B	109.7
C4—C3—C1	118.6 (4)	H10A—C10—H10B	108.2
C8—C3—C1	122.2 (4)	C12—C11—C10	112.5 (4)
C5—C4—C3	119.3 (4)	C12—C11—H11A	109.1
C5—C4—C2	120.8 (4)	C10—C11—H11A	109.1
C3—C4—C2	120.0 (4)	C12—C11—H11B	109.1
C4—C5—C6	121.3 (4)	C10—C11—H11B	109.1
C4—C5—Cl1	119.1 (3)	H11A—C11—H11B	107.8
C6—C5—Cl1	119.6 (3)	C11—C12—C12i	113.0 (5)
C7—C6—C5	119.4 (4)	C11—C12—H12A	109.0
C7—C6—Cl2	120.7 (3)	C12i—C12—H12A	109.0
C5—C6—Cl2	119.9 (4)	C11—C12—H12B	109.0
C6—C7—C8	120.0 (4)	C12i—C12—H12B	109.0
C6—C7—Cl3	119.9 (4)	H12A—C12—H12B	107.8
C8—C7—Cl3	120.1 (4)
C9—O1—C1—O2	1.0 (9)	C4—C5—C6—C7	1.5 (6)
C9—O1—C1—C3	−179.9 (5)	Cl1—C5—C6—C7	−178.4 (3)
O2—C1—C3—C4	−68.0 (7)	C4—C5—C6—Cl2	−177.0 (3)
O1—C1—C3—C4	112.9 (5)	Cl1—C5—C6—Cl2	3.1 (5)
O2—C1—C3—C8	106.7 (6)	C5—C6—C7—C8	2.3 (6)
O1—C1—C3—C8	−72.4 (6)	Cl2—C6—C7—C8	−179.3 (3)
C8—C3—C4—C5	1.6 (6)	C5—C6—C7—Cl3	−176.7 (3)
C1—C3—C4—C5	176.5 (4)	Cl2—C6—C7—Cl3	1.7 (5)
C8—C3—C4—C2	−176.8 (4)	C6—C7—C8—C3	−4.1 (7)
C1—C3—C4—C2	−1.8 (5)	Cl3—C7—C8—C3	174.9 (3)
O3—C2—C4—C5	101.7 (5)	C6—C7—C8—Cl4	177.5 (3)
O4—C2—C4—C5	−79.0 (5)	Cl3—C7—C8—Cl4	−3.6 (5)
O3—C2—C4—C3	−79.9 (5)	C4—C3—C8—C7	2.1 (6)
O4—C2—C4—C3	99.4 (4)	C1—C3—C8—C7	−172.6 (4)
C3—C4—C5—C6	−3.4 (6)	C4—C3—C8—Cl4	−179.4 (3)
C2—C4—C5—C6	174.9 (4)	C1—C3—C8—Cl4	5.9 (6)
C3—C4—C5—Cl1	176.5 (3)	N1—C10—C11—C12	−178.2 (4)
C2—C4—C5—Cl1	−5.2 (5)	C10—C11—C12—C12i	176.6 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O4	0.89	1.90	2.770 (5)	165
N1—H1B···O3ii	0.89	1.87	2.757 (5)	171
C9—H9B···Cl4iii	0.96	2.75	3.677 (9)	161
C10—H10B···O2	0.97	2.58	3.208 (7)	122

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O4	0.89	1.90	2.770 (5)	165
N1—H1B⋯O3i	0.89	1.87	2.757 (5)	171
C9—H9B⋯Cl4ii	0.96	2.75	3.677 (9)	161
C10—H10B⋯O2	0.97	2.58	3.208 (7)	122

Symmetry codes: (i) ; (ii) .