2,5-Dibenzoyl-benzene-1,4-diaminium dichloride.

The asymmetric unit of the title compound, C(20)H(18)N(2)O(2) (2+)·2Cl(-), is composed of one-half of the 2,5-dibenzoyl-benzene-1,4-diaminium dication, located on a centre of inversion, and one Cl(-) ion. The dihedral angle between the central benzene ring and the benzoyl phenyl ring is 53.3 (2)°. In the crystal structure, ions are linked to form a two-dimensional network parallel to the (10) plane by N-H⋯Cl hydrogen bonds.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For general background, see: Antoniadis et al. (1994 ▶); Imai et al. (1975 ▶); Kolosov et al. (2002 ▶); Tonzola et al. (2003 ▶).

Experimental

Crystal data

C20H18N2O2 2+·2Cl−

M = 389.26

Monoclinic,

a = 12.373 (3) Å

b = 5.195 (1) Å

c = 14.315 (3) Å

β = 104.46 (3)°

V = 891.0 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.38 mm−1

T = 298 (2) K

0.40 × 0.10 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.862, T max = 0.963

1754 measured reflections

1754 independent reflections

1232 reflections with I > 2σ(I)

3 standard reflections every 200 reflections intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.162

S = 1.08

1754 reflections

130 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.28 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1985 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Bruker, 2000 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807068730/ci2546sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807068730/ci2546Isup2.hkl

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

C20H18N2O22+·2Cl–	F000 = 404
Mr = 389.26	Dx = 1.451 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 12.373 (3) Å	θ = 9–13º
b = 5.195 (1) Å	µ = 0.38 mm−1
c = 14.315 (3) Å	T = 298 (2) K
β = 104.46 (3)º	Block, colourless
V = 891.0 (4) Å3	0.40 × 0.10 × 0.10 mm
Z = 2

Enraf–Nonius CAD-4 diffractometer	1232 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.0000
Monochromator: graphite	θmax = 26.0º
T = 298(2) K	θmin = 2.0º
ω/2θ scans	h = −15→14
Absorption correction: ψ scan(North et al., 1968)	k = 0→6
Tmin = 0.862, Tmax = 0.963	l = 0→17
1754 measured reflections	3 standard reflections
1754 independent reflections	every 200 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)] = 0.055	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.162	w = 1/[σ2(Fo2) + (0.0704P)2 + 0.5685P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max = 0.001
1754 reflections	Δρmax = 0.31 e Å−3
130 parameters	Δρmin = −0.27 e Å−3
3 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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
O1	0.2971 (2)	0.0151 (5)	−0.11097 (19)	0.0386 (7)
N1	0.6436 (3)	0.5247 (6)	0.1879 (2)	0.0265 (7)
H1N	0.635 (4)	0.655 (7)	0.224 (3)	0.073 (17)*
H2N	0.633 (3)	0.394 (7)	0.222 (3)	0.045 (12)*
H3N	0.714 (2)	0.517 (8)	0.188 (3)	0.040 (12)*
C1	0.1700 (4)	0.2318 (8)	0.1666 (3)	0.0438 (10)
H1	0.1688	0.3459	0.2164	0.053*
C2	0.1003 (3)	0.0237 (9)	0.1510 (3)	0.0450 (10)
H2	0.0508	−0.0008	0.1896	0.054*
C3	0.1022 (3)	−0.1489 (8)	0.0793 (3)	0.0442 (10)
H3	0.0558	−0.2922	0.0706	0.053*
C4	0.1732 (3)	−0.1104 (7)	0.0200 (3)	0.0372 (9)
H4	0.1731	−0.2260	−0.0296	0.045*
C5	0.2448 (3)	0.1002 (7)	0.0339 (3)	0.0274 (8)
C6	0.2430 (3)	0.2733 (7)	0.1081 (3)	0.0352 (9)
H6	0.2902	0.4154	0.1184	0.042*
C7	0.3141 (3)	0.1395 (6)	−0.0361 (2)	0.0262 (8)
C8	0.4074 (3)	0.3311 (6)	−0.0166 (2)	0.0230 (7)
C9	0.4812 (3)	0.3497 (7)	0.0737 (2)	0.0250 (7)
H9	0.4697	0.2484	0.1239	0.030*
C10	0.5707 (3)	0.5142 (6)	0.0907 (2)	0.0230 (7)
Cl1	0.59773 (8)	0.02097 (17)	0.29914 (7)	0.0350 (3)

	U11	U22	U33	U12	U13	U23
O1	0.0478 (16)	0.0345 (15)	0.0357 (14)	−0.0127 (13)	0.0148 (12)	−0.0065 (12)
N1	0.0268 (15)	0.0226 (16)	0.0272 (15)	−0.0029 (14)	0.0015 (12)	0.0026 (14)
C1	0.054 (3)	0.037 (2)	0.047 (2)	−0.004 (2)	0.025 (2)	−0.008 (2)
C2	0.039 (2)	0.051 (3)	0.050 (2)	0.002 (2)	0.0205 (19)	0.010 (2)
C3	0.041 (2)	0.035 (2)	0.060 (3)	−0.0108 (19)	0.019 (2)	0.004 (2)
C4	0.048 (2)	0.026 (2)	0.040 (2)	−0.0095 (18)	0.0165 (18)	−0.0018 (17)
C5	0.0274 (18)	0.0209 (17)	0.0343 (19)	−0.0024 (14)	0.0082 (15)	0.0009 (15)
C6	0.042 (2)	0.0258 (19)	0.039 (2)	−0.0010 (16)	0.0108 (17)	0.0012 (16)
C7	0.0291 (18)	0.0184 (16)	0.0309 (18)	0.0025 (14)	0.0070 (15)	0.0041 (14)
C8	0.0242 (16)	0.0171 (16)	0.0276 (17)	0.0007 (13)	0.0059 (13)	0.0017 (14)
C9	0.0307 (18)	0.0199 (17)	0.0254 (17)	−0.0008 (14)	0.0091 (14)	0.0050 (14)
C10	0.0284 (17)	0.0182 (16)	0.0214 (15)	0.0012 (14)	0.0046 (13)	−0.0003 (14)
Cl1	0.0418 (5)	0.0276 (5)	0.0393 (5)	0.0038 (4)	0.0168 (4)	0.0054 (4)

O1—C7	1.223 (4)	C4—C5	1.390 (5)
N1—C10	1.458 (4)	C4—H4	0.93
N1—H1N	0.87 (3)	C5—C6	1.396 (5)
N1—H2N	0.87 (3)	C5—C7	1.487 (5)
N1—H3N	0.87 (2)	C6—H6	0.93
C1—C2	1.366 (6)	C7—C8	1.497 (5)
C1—C6	1.393 (5)	C8—C9	1.388 (5)
C1—H1	0.93	C8—C10i	1.409 (4)
C2—C3	1.367 (6)	C9—C10	1.372 (5)
C2—H2	0.93	C9—H9	0.93
C3—C4	1.381 (5)	C10—C8i	1.409 (4)
C3—H3	0.93
C10—N1—H1N	117 (3)	C4—C5—C6	119.0 (3)
C10—N1—H2N	111 (3)	C4—C5—C7	117.7 (3)
H1N—N1—H2N	102 (4)	C6—C5—C7	123.1 (3)
C10—N1—H3N	112 (3)	C1—C6—C5	119.6 (4)
H1N—N1—H3N	108 (4)	C1—C6—H6	120.2
H2N—N1—H3N	105 (4)	C5—C6—H6	120.2
C2—C1—C6	120.1 (4)	O1—C7—C5	121.1 (3)
C2—C1—H1	119.9	O1—C7—C8	118.1 (3)
C6—C1—H1	119.9	C5—C7—C8	120.9 (3)
C1—C2—C3	120.8 (4)	C9—C8—C10i	117.1 (3)
C1—C2—H2	119.6	C9—C8—C7	121.2 (3)
C3—C2—H2	119.6	C10i—C8—C7	121.6 (3)
C2—C3—C4	120.0 (4)	C10—C9—C8	121.5 (3)
C2—C3—H3	120.0	C10—C9—H9	119.2
C4—C3—H3	120.0	C8—C9—H9	119.2
C3—C4—C5	120.4 (4)	C9—C10—C8i	121.4 (3)
C3—C4—H4	119.8	C9—C10—N1	118.1 (3)
C5—C4—H4	119.8	C8i—C10—N1	120.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···Cl1ii	0.87 (4)	2.29 (4)	3.155 (3)	172 (4)
N1—H2N···Cl1	0.87 (4)	2.33 (4)	3.187 (3)	174 (4)
N1—H3N···Cl1iii	0.87 (3)	2.29 (3)	3.159 (4)	175 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯Cl1i	0.87 (4)	2.29 (4)	3.155 (3)	172 (4)
N1—H2N⋯Cl1	0.87 (4)	2.33 (4)	3.187 (3)	174 (4)
N1—H3N⋯Cl1ii	0.87 (3)	2.29 (3)	3.159 (4)	175 (2)

Symmetry codes: (i) ; (ii) .