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

In the title salt, C(4)H(14)N(2) (+)·2C(9)H(3)Cl(4)O(4) (-), the cation lies on an inversion center. In the anion, the mean planes of meth-oxy-carbonyl and carboxyl-ate groups form dihedral angles of 64.9 (3) and 58.5 (3)°, respectively, with the benzene ring. In the crystal, inter-molecular N-H⋯O hydrogen bonds connect the components into sheets parallel to (100).

Related literature

For a related structure, see: Li (2011 ▶).

Experimental

Crystal data

C4H14N2 2+·2C9H3Cl4O4 −

M = 724.00

Monoclinic,

a = 14.4243 (13) Å

b = 6.1041 (6) Å

c = 16.9653 (15) Å

β = 97.056 (1)°

V = 1482.4 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.81 mm−1

T = 298 K

0.46 × 0.43 × 0.40 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1997 ▶) T min = 0.708, T max = 0.738

7307 measured reflections

2603 independent reflections

1908 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.096

S = 1.05

2603 reflections

183 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.20 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 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811016795/lh5244sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811016795/lh5244Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811016795/lh5244Isup3.cml

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

C4H14N22+·2C9H3Cl4O4−	F(000) = 732
Mr = 724.00	Dx = 1.622 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2612 reflections
a = 14.4243 (13) Å	θ = 2.4–26.5°
b = 6.1041 (6) Å	µ = 0.81 mm−1
c = 16.9653 (15) Å	T = 298 K
β = 97.056 (1)°	Block, colorless
V = 1482.4 (2) Å3	0.46 × 0.43 × 0.40 mm
Z = 2

Bruker SMART CCD diffractometer	2603 independent reflections
Radiation source: fine-focus sealed tube	1908 reflections with I > 2σ(I)
graphite	Rint = 0.024
φ and ω scans	θmax = 25.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −9→17
Tmin = 0.708, Tmax = 0.738	k = −7→7
7307 measured reflections	l = −18→20

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0373P)2 + 1.0059P] where P = (Fo2 + 2Fc2)/3
2603 reflections	(Δ/σ)max < 0.001
183 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.20 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	0.27338 (6)	0.79357 (15)	0.17344 (4)	0.0617 (3)
Cl2	0.10875 (6)	1.10088 (15)	0.19656 (5)	0.0705 (3)
Cl3	0.01193 (5)	1.07644 (14)	0.34929 (5)	0.0642 (3)
Cl4	0.07322 (6)	0.72291 (15)	0.47687 (5)	0.0630 (3)
N1	0.46526 (16)	0.9951 (4)	0.31490 (13)	0.0465 (6)
H1A	0.4416	0.8603	0.3128	0.070*
H1B	0.5002	1.0132	0.2756	0.070*
H1C	0.4189	1.0923	0.3099	0.070*
O1	0.19109 (14)	0.3094 (3)	0.46777 (12)	0.0559 (5)
O2	0.32465 (15)	0.4957 (4)	0.48905 (13)	0.0675 (6)
O3	0.31815 (14)	0.2789 (3)	0.31198 (14)	0.0626 (6)
O4	0.41355 (12)	0.5599 (3)	0.30166 (11)	0.0459 (5)
C1	0.24890 (19)	0.4667 (5)	0.45324 (15)	0.0415 (6)
C2	0.33628 (19)	0.4761 (4)	0.30956 (14)	0.0379 (6)
C3	0.20896 (17)	0.6149 (4)	0.38674 (15)	0.0376 (6)
C4	0.25510 (17)	0.6303 (4)	0.31904 (15)	0.0358 (6)
C5	0.22239 (18)	0.7791 (4)	0.26073 (15)	0.0390 (6)
C6	0.14757 (18)	0.9170 (4)	0.26928 (16)	0.0428 (7)
C7	0.10285 (18)	0.9025 (4)	0.33718 (17)	0.0430 (7)
C8	0.13250 (18)	0.7475 (5)	0.39497 (16)	0.0415 (7)
C9	0.2212 (2)	0.1710 (6)	0.53489 (19)	0.0662 (9)
H9A	0.2630	0.0610	0.5195	0.099*
H9B	0.1679	0.1018	0.5529	0.099*
H9C	0.2529	0.2581	0.5770	0.099*
C10	0.5233 (2)	1.0276 (6)	0.39168 (18)	0.0619 (9)
H10A	0.5461	1.1772	0.3950	0.074*
H10B	0.5770	0.9309	0.3947	0.074*
C11	0.4702 (2)	0.9828 (6)	0.46041 (17)	0.0578 (8)
H11A	0.4477	0.8330	0.4572	0.069*
H11B	0.4163	1.0791	0.4572	0.069*

	U11	U22	U33	U12	U13	U23
Cl1	0.0654 (5)	0.0794 (6)	0.0435 (4)	0.0200 (4)	0.0191 (4)	0.0101 (4)
Cl2	0.0592 (5)	0.0752 (6)	0.0774 (6)	0.0234 (5)	0.0093 (4)	0.0269 (5)
Cl3	0.0443 (4)	0.0644 (5)	0.0856 (6)	0.0176 (4)	0.0143 (4)	−0.0125 (4)
Cl4	0.0541 (5)	0.0812 (6)	0.0597 (5)	0.0003 (4)	0.0309 (4)	−0.0073 (4)
N1	0.0478 (14)	0.0430 (13)	0.0528 (14)	0.0035 (11)	0.0233 (11)	0.0023 (11)
O1	0.0553 (13)	0.0521 (12)	0.0602 (13)	−0.0123 (11)	0.0065 (10)	0.0088 (10)
O2	0.0502 (13)	0.0832 (16)	0.0665 (14)	−0.0169 (12)	−0.0032 (11)	0.0221 (12)
O3	0.0513 (13)	0.0355 (12)	0.1034 (18)	0.0027 (10)	0.0198 (12)	−0.0069 (11)
O4	0.0376 (11)	0.0456 (11)	0.0581 (12)	0.0035 (9)	0.0206 (9)	−0.0009 (9)
C1	0.0385 (16)	0.0471 (17)	0.0407 (15)	−0.0064 (13)	0.0117 (13)	−0.0019 (12)
C2	0.0390 (16)	0.0385 (16)	0.0372 (14)	0.0043 (13)	0.0087 (12)	−0.0014 (11)
C3	0.0320 (14)	0.0382 (15)	0.0433 (14)	−0.0038 (12)	0.0076 (11)	−0.0036 (12)
C4	0.0319 (14)	0.0339 (14)	0.0424 (14)	−0.0005 (11)	0.0077 (11)	−0.0051 (11)
C5	0.0352 (15)	0.0435 (15)	0.0393 (14)	0.0011 (12)	0.0083 (11)	−0.0043 (12)
C6	0.0357 (15)	0.0415 (16)	0.0502 (16)	0.0029 (13)	0.0014 (12)	0.0003 (13)
C7	0.0308 (14)	0.0415 (16)	0.0572 (17)	0.0040 (12)	0.0074 (13)	−0.0096 (13)
C8	0.0335 (14)	0.0487 (17)	0.0448 (15)	−0.0025 (13)	0.0144 (12)	−0.0093 (13)
C9	0.077 (2)	0.062 (2)	0.063 (2)	−0.0074 (19)	0.0209 (18)	0.0136 (17)
C10	0.0485 (19)	0.082 (2)	0.057 (2)	−0.0095 (17)	0.0134 (15)	0.0004 (17)
C11	0.0532 (19)	0.067 (2)	0.0557 (18)	−0.0077 (17)	0.0179 (15)	0.0026 (16)

Cl1—C5	1.735 (3)	C3—C8	1.389 (4)
Cl2—C6	1.711 (3)	C3—C4	1.400 (3)
Cl3—C7	1.719 (3)	C4—C5	1.382 (4)
Cl4—C8	1.725 (3)	C5—C6	1.390 (4)
N1—C10	1.473 (4)	C6—C7	1.390 (4)
N1—H1A	0.8900	C7—C8	1.391 (4)
N1—H1B	0.8900	C9—H9A	0.9600
N1—H1C	0.8900	C9—H9B	0.9600
O1—C1	1.314 (3)	C9—H9C	0.9600
O1—C9	1.441 (4)	C10—C11	1.497 (4)
O2—C1	1.196 (3)	C10—H10A	0.9700
O3—C2	1.234 (3)	C10—H10B	0.9700
O4—C2	1.248 (3)	C11—C11i	1.518 (6)
C1—C3	1.504 (4)	C11—H11A	0.9700
C2—C4	1.526 (3)	C11—H11B	0.9700
C10—N1—H1A	109.5	C6—C7—C8	119.6 (2)
C10—N1—H1B	109.5	C6—C7—Cl3	119.9 (2)
H1A—N1—H1B	109.5	C8—C7—Cl3	120.6 (2)
C10—N1—H1C	109.5	C3—C8—C7	120.3 (2)
H1A—N1—H1C	109.5	C3—C8—Cl4	120.6 (2)
H1B—N1—H1C	109.5	C7—C8—Cl4	119.1 (2)
C1—O1—C9	116.1 (2)	O1—C9—H9A	109.5
O2—C1—O1	125.0 (3)	O1—C9—H9B	109.5
O2—C1—C3	122.2 (3)	H9A—C9—H9B	109.5
O1—C1—C3	112.7 (2)	O1—C9—H9C	109.5
O3—C2—O4	126.8 (3)	H9A—C9—H9C	109.5
O3—C2—C4	115.5 (2)	H9B—C9—H9C	109.5
O4—C2—C4	117.7 (2)	N1—C10—C11	112.0 (2)
C8—C3—C4	120.5 (2)	N1—C10—H10A	109.2
C8—C3—C1	120.7 (2)	C11—C10—H10A	109.2
C4—C3—C1	118.6 (2)	N1—C10—H10B	109.2
C5—C4—C3	118.5 (2)	C11—C10—H10B	109.2
C5—C4—C2	121.9 (2)	H10A—C10—H10B	107.9
C3—C4—C2	119.6 (2)	C10—C11—C11i	112.1 (3)
C4—C5—C6	121.6 (2)	C10—C11—H11A	109.2
C4—C5—Cl1	120.1 (2)	C11i—C11—H11A	109.2
C6—C5—Cl1	118.3 (2)	C10—C11—H11B	109.2
C5—C6—C7	119.5 (2)	C11i—C11—H11B	109.2
C5—C6—Cl2	120.8 (2)	H11A—C11—H11B	107.9
C7—C6—Cl2	119.7 (2)
C9—O1—C1—O2	3.3 (4)	C4—C5—C6—C7	−1.5 (4)
C9—O1—C1—C3	−175.2 (2)	Cl1—C5—C6—C7	177.3 (2)
O2—C1—C3—C8	−112.4 (3)	C4—C5—C6—Cl2	179.6 (2)
O1—C1—C3—C8	66.2 (3)	Cl1—C5—C6—Cl2	−1.6 (3)
O2—C1—C3—C4	62.3 (4)	C5—C6—C7—C8	−1.2 (4)
O1—C1—C3—C4	−119.2 (3)	Cl2—C6—C7—C8	177.8 (2)
C8—C3—C4—C5	−0.4 (4)	C5—C6—C7—Cl3	178.6 (2)
C1—C3—C4—C5	−175.1 (2)	Cl2—C6—C7—Cl3	−2.5 (3)
C8—C3—C4—C2	−177.3 (2)	C4—C3—C8—C7	−2.2 (4)
C1—C3—C4—C2	8.0 (4)	C1—C3—C8—C7	172.4 (2)
O3—C2—C4—C5	−119.9 (3)	C4—C3—C8—Cl4	178.0 (2)
O4—C2—C4—C5	61.3 (3)	C1—C3—C8—Cl4	−7.5 (3)
O3—C2—C4—C3	56.9 (3)	C6—C7—C8—C3	3.0 (4)
O4—C2—C4—C3	−121.9 (3)	Cl3—C7—C8—C3	−176.8 (2)
C3—C4—C5—C6	2.3 (4)	C6—C7—C8—Cl4	−177.2 (2)
C2—C4—C5—C6	179.1 (2)	Cl3—C7—C8—Cl4	3.1 (3)
C3—C4—C5—Cl1	−176.52 (19)	N1—C10—C11—C11i	−179.8 (3)
C2—C4—C5—Cl1	0.3 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1C···O3ii	0.89	1.85	2.735 (3)	172
N1—H1B···O4iii	0.89	1.94	2.823 (3)	174
N1—H1A···O4	0.89	1.88	2.761 (3)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1C⋯O3i	0.89	1.85	2.735 (3)	172
N1—H1B⋯O4ii	0.89	1.94	2.823 (3)	174
N1—H1A⋯O4	0.89	1.88	2.761 (3)	169

Symmetry codes: (i) ; (ii) .