4,4′-Dichloro-N,N′-(o-phenyl­ene)dibenzene­sulfonamide

Krainova, J.; Dares, C.; Lever, A.B.P.

doi:10.1107/S1600536808039718

organic compounds

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ISSN: 2056-9890

Volume 65| Part 1| January 2009| Page o178

doi:10.1107/S1600536808039718

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4,4′-Dichloro-N,N′-(o-phenylene)dibenzenesulfonamide

Julia Krainova,^a Christopher Dares ^a and A. B. P. Lever ^a ^*

^aDepartment of Chemistry, York University, Toronto, Ontario, Canada M3J 1P3
^*Correspondence e-mail: blever@yorku.ca

(Received 6 November 2008; accepted 25 November 2008; online 20 December 2008)

The title compound, C₁₈H₁₄Cl₂N₂O₄S₂, is a diamine that is a precursor to a quinonoid bidentate redox-active ligand. The dihedral angles between the central phenyl ring and the end rings are 87.5(1) and 60.7(1)°, while the two end rings make a dihedral angle of 82.5(1)°. The crystal structure is stabilized by two weak intermolecular N—H⋯O hydrogen bonds, as well as one intramolecular C—H⋯O and one N—H⋯N hydrogen bond.

Related literature

For the synthesis of related substituted o-phenylenediamines, see: Massacret et al. (1999 ). For background to the use of substituted o-benzoquinones as ligands, see: Masui & Lever (1993 ); Kalinina et al. (2008 ) and references therein.

Experimental

Crystal data

C₁₈H₁₄Cl₂N₂O₄S₂
M_r = 457.33
Triclinic, $[P \overline 1]$
a = 7.7225 (4) Å
b = 11.1920 (4) Å
c = 11.9325 (5) Å
α = 109.669 (2)°
β = 91.420 (2)°
γ = 101.782 (2)°
V = 945.79 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.59 mm⁻¹
T = 150 (1) K
0.40 × 0.36 × 0.30 mm

Data collection

Bruker–Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SORTAV; Blessing, 1995 ) T_min = 0.748, T_max = 0.876
8650 measured reflections
4235 independent reflections
3386 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.122
S = 1.08
4235 reflections
261 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.69 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O4ⁱ	0.87 (3)	2.12 (3)	2.936 (3)	157 (2)
N2—H2⋯O2ⁱⁱ	0.85 (3)	2.30 (3)	3.107 (3)	159 (2)
N1—H1⋯N2	0.87 (3)	2.45 (3)	2.811 (3)	106 (2)
C6—H6⋯O1	0.95	2.22	2.900 (3)	128
Symmetry codes: (i) -x, -y+1, -z+1; (ii) x-1, y, z.

Data collection: COLLECT (Nonius, 2002 ); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 ); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808039718/bx2184sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808039718/bx2184Isup2.hkl

checkCIF report

Comment top

Benzoquinonediimine compounds have been extensively studied as ligands in metal complex systems (Kalinina et al., 2008). As free ligands, they exist in the diamine form, however, they have the ability to bind to a metal in one of three oxidation states: as o-phenylenediamine, its one-electron oxidized o-semiquinonediiminate, or its doubly oxidized and strongly π-accepting o-benzoquinonediimine form. In addition to being redox-active, these ligands also often exhibit non-innocent behaviour. Ruthenium complexes of o-benzoquinonediimines possess highly covalent bonds. The extent of electronic coupling between the metal and diimine ligand can be tuned by using substituented o-benzoquinones (Masui & Lever, 1993, and Kalinina et al., 2008). We present here the synthesis and crystal structure of the title compound (I). In (I) (Fig. 1), highly electron-withdrawing groups (p-chlorophenylsulfonyl, PCPS) are bound to the amine N atoms, and are expected to exhibit a greater covalent metal-benzoquinonediimine ligand bond character than the unsubstituted diimine. The C1—N1—S1—C7 dihedral angle is 81.0 (2) °, while the C2—N2—S2—C13 dihedral angle is only 68.6 (2)°. The p-chlorophenyl rings are essentially perpendicular to the N—S bond, likely due to steric hindrance and intermolecular H bonding between the ortho H atoms, and the sulfonyl O atoms (Fig. 1). The crystal structure is stabilized by two weak intermolecular N—H···O hydrogen bonds (Fig. 2), as well as three intramolecular C—H···O and one N—H···N hydrogen bonds which increases the stability of the crystal, (Table 1). The bonds parameters are similar to those in the other arylsulfonamides.

Related literature top

For the synthesis of related substituted o-phenylenediamines, see: Massacret et al. (1999). For background to the use of substituted o-benzoquinones as ligands, see: Masui & Lever (1993); Kalinina et al. (2008) and references therein.

Experimental top

(I) was synthesized for the first time according to methods described by Massacret et al., 1999, using p-chlorophenylsulfonyl chloride (10 mmol) as the arenesulfonyl chloride. o-phenylenediamine (540 mg, 5 mmol) was twice sublimed under reduced pressure prior to use. After purification, (I) was dissolved in a minimal amount of ethanol, and then added to an aqueous solution of CuCl₂ (20 ml, 0.15 M). Colorless block-like crystals suitable for x-ray diffraction studies were obtained after allowing the solution to stand for 2 weeks.

Computing details top

Data collection: COLLECT (Nonius, 2002); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. A view of (I) showing the molecular structure and intramolecular H bonding present. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. Crystal packing diagram of (I) showing the intermolecular H bonds present. H atoms not involved in H bonding are not shown. Displacement ellipsoids are drawn at the 30% probability level.

4,4'-Dichloro-N,N'-(o-phenylene)dibenzenesulfonamide top

Crystal data top

C₁₈H₁₄Cl₂N₂O₄S₂	Z = 2
M_r = 457.33	F(000) = 468
Triclinic, P1	D_x = 1.606 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.7225 (4) Å	Cell parameters from 4103 reflections
b = 11.1920 (4) Å	θ = 2.6–27.5°
c = 11.9325 (5) Å	µ = 0.59 mm⁻¹
α = 109.669 (2)°	T = 150 K
β = 91.420 (2)°	Prism, colourless
γ = 101.782 (2)°	0.40 × 0.36 × 0.30 mm
V = 945.79 (7) Å³

Data collection top

Bruker–Nonius KappaCCD diffractometer	4235 independent reflections
Radiation source: fine-focus sealed tube	3386 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
ϕ scans and ω scans with κ offsets	θ_max = 27.5°, θ_min = 2.7°
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	h = −10→9
T_min = 0.748, T_max = 0.876	k = −14→14
8650 measured reflections	l = −14→15

Refinement top

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.122	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ²(F_o²) + (0.06P)² + 0.6434P] where P = (F_o² + 2F_c²)/3
4235 reflections	(Δ/σ)_max < 0.001
261 parameters	Δρ_max = 0.48 e Å⁻³
0 restraints	Δρ_min = −0.69 e Å⁻³

Crystal data top

C₁₈H₁₄Cl₂N₂O₄S₂	γ = 101.782 (2)°
M_r = 457.33	V = 945.79 (7) Å³
Triclinic, P1	Z = 2
a = 7.7225 (4) Å	Mo Kα radiation
b = 11.1920 (4) Å	µ = 0.59 mm⁻¹
c = 11.9325 (5) Å	T = 150 K
α = 109.669 (2)°	0.40 × 0.36 × 0.30 mm
β = 91.420 (2)°

Data collection top

Bruker–Nonius KappaCCD diffractometer	4235 independent reflections
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	3386 reflections with I > 2σ(I)
T_min = 0.748, T_max = 0.876	R_int = 0.032
8650 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.122	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	Δρ_max = 0.48 e Å⁻³
4235 reflections	Δρ_min = −0.69 e Å⁻³
261 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.1732 (3)	0.8391 (2)	0.77764 (19)	0.0171 (4)
C2	−0.0029 (3)	0.8152 (2)	0.72753 (19)	0.0171 (4)
C3	−0.1000 (3)	0.9105 (2)	0.7632 (2)	0.0222 (5)
H3	−0.2178	0.8935	0.7273	0.027*
C4	−0.0274 (3)	1.0303 (2)	0.8506 (2)	0.0262 (5)
H4	−0.0940	1.0957	0.8744	0.031*
C5	0.1440 (3)	1.0528 (2)	0.9026 (2)	0.0257 (5)
H5	0.1934	1.1333	0.9646	0.031*
C6	0.2444 (3)	0.9599 (2)	0.8657 (2)	0.0225 (5)
H6	0.3630	0.9785	0.9008	0.027*
C7	0.3601 (3)	0.6325 (2)	0.8929 (2)	0.0195 (5)
C8	0.3196 (3)	0.4973 (2)	0.8469 (2)	0.0270 (5)
H8	0.3392	0.4524	0.7669	0.032*
C9	0.2500 (4)	0.4285 (3)	0.9191 (2)	0.0314 (6)
H9	0.2220	0.3360	0.8891	0.038*
C10	0.2220 (3)	0.4956 (3)	1.0349 (2)	0.0284 (6)
C11	0.2637 (4)	0.6307 (3)	1.0819 (2)	0.0310 (6)
H11	0.2448	0.6752	1.1622	0.037*
C12	0.3334 (3)	0.7000 (2)	1.0100 (2)	0.0266 (5)
H12	0.3625	0.7925	1.0405	0.032*
C13	−0.2243 (3)	0.7466 (2)	0.45683 (19)	0.0189 (4)
C14	−0.4080 (3)	0.7072 (2)	0.4534 (2)	0.0210 (5)
H14	−0.4581	0.6378	0.4801	0.025*
C15	−0.5169 (3)	0.7697 (2)	0.4109 (2)	0.0225 (5)
H15	−0.6425	0.7440	0.4078	0.027*
C16	−0.4392 (3)	0.8706 (2)	0.3730 (2)	0.0236 (5)
C17	−0.2571 (3)	0.9119 (2)	0.3774 (2)	0.0264 (5)
H17	−0.2077	0.9826	0.3523	0.032*
C18	−0.1476 (3)	0.8486 (2)	0.4190 (2)	0.0233 (5)
H18	−0.0221	0.8745	0.4217	0.028*
N1	0.2723 (3)	0.7422 (2)	0.73182 (17)	0.0203 (4)
H1	0.222 (4)	0.673 (3)	0.672 (3)	0.024*
N2	−0.0870 (3)	0.68766 (18)	0.64404 (17)	0.0191 (4)
H2	−0.188 (4)	0.654 (3)	0.660 (2)	0.023*
O1	0.5452 (2)	0.84388 (16)	0.87507 (14)	0.0235 (4)
O2	0.5228 (2)	0.63638 (16)	0.70620 (14)	0.0232 (4)
O3	0.0908 (2)	0.70716 (18)	0.48023 (15)	0.0289 (4)
O4	−0.1729 (2)	0.52320 (16)	0.44441 (16)	0.0311 (4)
S1	0.44267 (7)	0.71968 (5)	0.79949 (5)	0.01842 (15)
S2	−0.08688 (7)	0.65782 (5)	0.50003 (5)	0.02006 (15)
Cl1	0.13235 (9)	0.40953 (8)	1.12463 (7)	0.0420 (2)
Cl2	−0.57712 (9)	0.94836 (6)	0.31859 (6)	0.03448 (18)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0178 (11)	0.0206 (11)	0.0154 (10)	0.0057 (9)	0.0010 (8)	0.0087 (9)
C2	0.0169 (11)	0.0195 (11)	0.0155 (10)	0.0034 (9)	0.0013 (8)	0.0072 (9)
C3	0.0196 (11)	0.0263 (12)	0.0237 (12)	0.0074 (10)	0.0014 (9)	0.0111 (10)
C4	0.0310 (13)	0.0252 (12)	0.0241 (12)	0.0123 (11)	0.0056 (10)	0.0073 (10)
C5	0.0331 (14)	0.0221 (12)	0.0188 (11)	0.0067 (10)	−0.0031 (10)	0.0032 (10)
C6	0.0243 (12)	0.0210 (11)	0.0196 (11)	0.0035 (9)	−0.0048 (9)	0.0051 (9)
C7	0.0163 (11)	0.0256 (12)	0.0180 (11)	0.0072 (9)	−0.0012 (8)	0.0080 (9)
C8	0.0342 (14)	0.0255 (12)	0.0223 (12)	0.0102 (11)	0.0037 (10)	0.0075 (10)
C9	0.0379 (15)	0.0261 (13)	0.0343 (14)	0.0084 (11)	0.0036 (12)	0.0152 (12)
C10	0.0251 (13)	0.0389 (15)	0.0296 (13)	0.0096 (11)	0.0007 (10)	0.0216 (12)
C11	0.0324 (14)	0.0425 (15)	0.0190 (12)	0.0094 (12)	0.0044 (10)	0.0111 (11)
C12	0.0285 (13)	0.0278 (13)	0.0221 (12)	0.0066 (11)	0.0007 (10)	0.0070 (10)
C13	0.0195 (11)	0.0224 (11)	0.0141 (10)	0.0064 (9)	−0.0012 (8)	0.0046 (9)
C14	0.0193 (11)	0.0251 (12)	0.0205 (11)	0.0063 (9)	0.0027 (9)	0.0096 (9)
C15	0.0181 (11)	0.0296 (13)	0.0212 (11)	0.0089 (10)	0.0029 (9)	0.0086 (10)
C16	0.0312 (13)	0.0268 (12)	0.0152 (11)	0.0162 (11)	−0.0017 (9)	0.0052 (9)
C17	0.0319 (14)	0.0242 (12)	0.0243 (12)	0.0032 (10)	−0.0019 (10)	0.0120 (10)
C18	0.0199 (12)	0.0268 (12)	0.0226 (12)	0.0023 (10)	−0.0006 (9)	0.0096 (10)
N1	0.0183 (10)	0.0222 (10)	0.0185 (9)	0.0057 (8)	−0.0048 (8)	0.0046 (8)
N2	0.0154 (9)	0.0202 (10)	0.0208 (10)	0.0005 (8)	−0.0030 (8)	0.0084 (8)
O1	0.0170 (8)	0.0242 (9)	0.0245 (8)	−0.0009 (7)	−0.0062 (7)	0.0062 (7)
O2	0.0180 (8)	0.0303 (9)	0.0220 (8)	0.0080 (7)	0.0014 (6)	0.0087 (7)
O3	0.0194 (9)	0.0431 (11)	0.0265 (9)	0.0115 (8)	0.0040 (7)	0.0126 (8)
O4	0.0343 (10)	0.0182 (8)	0.0327 (10)	0.0087 (8)	−0.0144 (8)	−0.0017 (7)
S1	0.0146 (3)	0.0234 (3)	0.0175 (3)	0.0048 (2)	−0.0017 (2)	0.0074 (2)
S2	0.0180 (3)	0.0221 (3)	0.0189 (3)	0.0076 (2)	−0.0027 (2)	0.0043 (2)
Cl1	0.0365 (4)	0.0621 (5)	0.0440 (4)	0.0103 (3)	0.0061 (3)	0.0403 (4)
Cl2	0.0453 (4)	0.0365 (4)	0.0275 (3)	0.0237 (3)	−0.0036 (3)	0.0107 (3)

Geometric parameters (Å, º) top

C1—C6	1.395 (3)	C11—H11	0.9500
C1—C2	1.408 (3)	C12—H12	0.9500
C1—N1	1.422 (3)	C13—C14	1.392 (3)
C2—C3	1.385 (3)	C13—C18	1.393 (3)
C2—N2	1.443 (3)	C13—S2	1.769 (2)
C3—C4	1.387 (3)	C14—C15	1.382 (3)
C3—H3	0.9500	C14—H14	0.9500
C4—C5	1.385 (4)	C15—C16	1.386 (3)
C4—H4	0.9500	C15—H15	0.9500
C5—C6	1.383 (3)	C16—C17	1.381 (4)
C5—H5	0.9500	C16—Cl2	1.743 (2)
C6—H6	0.9500	C17—C18	1.387 (3)
C7—C8	1.388 (3)	C17—H17	0.9500
C7—C12	1.390 (3)	C18—H18	0.9500
C7—S1	1.764 (2)	N1—S1	1.6329 (18)
C8—C9	1.387 (3)	N1—H1	0.87 (3)
C8—H8	0.9500	N2—S2	1.637 (2)
C9—C10	1.380 (4)	N2—H2	0.85 (3)
C9—H9	0.9500	O1—S1	1.4296 (17)
C10—C11	1.388 (4)	O2—S1	1.4359 (17)
C10—Cl1	1.735 (3)	O3—S2	1.4278 (18)
C11—C12	1.388 (4)	O4—S2	1.4312 (17)

C6—C1—C2	118.0 (2)	C14—C13—C18	121.3 (2)
C6—C1—N1	123.3 (2)	C14—C13—S2	119.09 (17)
C2—C1—N1	118.56 (19)	C18—C13—S2	119.43 (18)
C3—C2—C1	120.5 (2)	C15—C14—C13	119.5 (2)
C3—C2—N2	119.54 (19)	C15—C14—H14	120.3
C1—C2—N2	119.79 (19)	C13—C14—H14	120.3
C2—C3—C4	120.8 (2)	C14—C15—C16	118.7 (2)
C2—C3—H3	119.6	C14—C15—H15	120.6
C4—C3—H3	119.6	C16—C15—H15	120.6
C5—C4—C3	118.7 (2)	C17—C16—C15	122.4 (2)
C5—C4—H4	120.6	C17—C16—Cl2	119.05 (19)
C3—C4—H4	120.6	C15—C16—Cl2	118.53 (19)
C6—C5—C4	121.1 (2)	C16—C17—C18	119.0 (2)
C6—C5—H5	119.4	C16—C17—H17	120.5
C4—C5—H5	119.4	C18—C17—H17	120.5
C5—C6—C1	120.7 (2)	C17—C18—C13	119.1 (2)
C5—C6—H6	119.6	C17—C18—H18	120.5
C1—C6—H6	119.6	C13—C18—H18	120.5
C8—C7—C12	121.3 (2)	C1—N1—S1	127.72 (16)
C8—C7—S1	119.10 (18)	C1—N1—H1	117.6 (18)
C12—C7—S1	119.63 (18)	S1—N1—H1	112.0 (18)
C9—C8—C7	119.2 (2)	C2—N2—S2	119.94 (15)
C9—C8—H8	120.4	C2—N2—H2	115.3 (19)
C7—C8—H8	120.4	S2—N2—H2	110.4 (18)
C10—C9—C8	119.5 (2)	O1—S1—O2	119.90 (10)
C10—C9—H9	120.3	O1—S1—N1	108.49 (10)
C8—C9—H9	120.3	O2—S1—N1	105.21 (10)
C9—C10—C11	121.6 (2)	O1—S1—C7	107.30 (10)
C9—C10—Cl1	119.4 (2)	O2—S1—C7	107.80 (11)
C11—C10—Cl1	119.0 (2)	N1—S1—C7	107.61 (10)
C12—C11—C10	119.1 (2)	O3—S2—O4	121.51 (12)
C12—C11—H11	120.4	O3—S2—N2	106.60 (10)
C10—C11—H11	120.4	O4—S2—N2	105.45 (11)
C11—C12—C7	119.3 (2)	O3—S2—C13	107.47 (11)
C11—C12—H12	120.3	O4—S2—C13	106.22 (10)
C7—C12—H12	120.3	N2—S2—C13	109.20 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4ⁱ	0.87 (3)	2.12 (3)	2.936 (3)	157 (2)
N2—H2···O2ⁱⁱ	0.85 (3)	2.30 (3)	3.107 (3)	159 (2)
N1—H1···N2	0.87 (3)	2.45 (3)	2.811 (3)	106 (2)
C6—H6···O1	0.95	2.22	2.900 (3)	128
C8—H8···O2	0.95	2.58	2.931 (3)	103
C18—H18···O3	0.95	2.50	2.887 (3)	104

Symmetry codes: (i) −x, −y+1, −z+1; (ii) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₄Cl₂N₂O₄S₂
M_r	457.33
Crystal system, space group	Triclinic, P1
Temperature (K)	150
a, b, c (Å)	7.7225 (4), 11.1920 (4), 11.9325 (5)
α, β, γ (°)	109.669 (2), 91.420 (2), 101.782 (2)
V (Å³)	945.79 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.59
Crystal size (mm)	0.40 × 0.36 × 0.30

Data collection
Diffractometer	Bruker–Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (SORTAV; Blessing, 1995)
T_min, T_max	0.748, 0.876
No. of measured, independent and observed [I > 2σ(I)] reflections	8650, 4235, 3386
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.122, 1.08
No. of reflections	4235
No. of parameters	261
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.48, −0.69

Computer programs: COLLECT (Nonius, 2002), DENZO-SMN (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4ⁱ	0.87 (3)	2.12 (3)	2.936 (3)	157 (2)
N2—H2···O2ⁱⁱ	0.85 (3)	2.30 (3)	3.107 (3)	159 (2)
N1—H1···N2	0.87 (3)	2.45 (3)	2.811 (3)	106 (2)
C6—H6···O1	0.95	2.22	2.900 (3)	127.9
C8—H8···O2	0.95	2.58	2.931 (3)	102.5
C18—H18···O3	0.95	2.50	2.887 (3)	104.1

Symmetry codes: (i) −x, −y+1, −z+1; (ii) x−1, y, z.

Acknowledgements

The authors thank Dr Alan J. Lough for acquiring the X-ray diffraction data and for helpful discussions. Financial support for this work was provided by the Natural Sciences and Engineering Research Council of Canada (NSERC). CD thanks NSERC for a post-graduate scholarship.

References

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