9-Di­cyano­methyl­ene-4,5-di­nitro­fluorene-2,7-disulfon­amide

Batsanov, A.S.; Perepichka, I.F.

doi:10.1107/S160053680402361X

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 60| Part 10| October 2004| Pages o1892-o1894

https://doi.org/10.1107/S160053680402361X

9-Dicyanomethylene-4,5-dinitrofluorene-2,7-disulfonamide

Andrei S. Batsanov ^a ^* and Igor F. Perepichka ^a

^aDepartment of Chemistry, University of Durham, South Road, Durham DH1 3LE, England
^*Correspondence e-mail: a.s.batsanov@durham.ac.uk

(Received 15 September 2004; accepted 22 September 2004; online 30 September 2004)

The title compound, C₁₆H₈N₆O₈S₂, has a twisted fluorene moiety due to steric repulsion between the 4- and 5-nitro groups.

Comment

2,4,5,7-Tetranitro-9-dicyanomethylenefluorene (DTeF) (Silverman et al., 1974 ) is a strong electron acceptor, used as a component of charge-transfer complexes (CTC) (Perepichka et al., 1998 ; Batsanov, Bryce et al., 2001 ; Batsanov, Perepichka et al., 2001 ). We also prepared and structurally characterized similar complexes with 2,7-bis(n-butylsulfonyl)- and 2,7-bis(phenylsulfonyl)-9-dicyanomethylene-4,5-dinitrofluorene (Perepichka et al., 2000 ). The title compound, (I), was prepared in the course of the same study.

The fluorene system of (I), like that of DTeF, adopts a twisted conformation (Fig. 1), due to steric repulsion between the nitro groups in positions 4 and 5 [intramolecular contacts O42⋯N5 = 2.646 (5) Å and O51⋯N4 = 2.674 (5) Å]. The strain is relieved by (i) both nitro groups tilting out of the aromatic plane in opposite directions and (ii) the fluorene moiety itself twisting substantially. Thus, the 13 C atoms of the fluorene moiety show an average deviation of 0.13 Å from their mean plane. Both benzene rings adopt `sofa' conformations, atoms C11 and C12 deviating by 0.12 and 0.06 Å from the planes of the essentially planar moieties C1–C4/C10 and C5–C8/C13, respectively. The latter planes form a dihedral angle of 15.2 (3)°. The twist around the C9=C14 bond, i.e. the dihedral angle between the C9/C10/C13/C14 and C9/C14/C15/C16/N15/N16 planes, is 11.5 (3)°. The bond lengths and angles in (I) (Table 1) are consistent with those observed in other distorted fluorene systems.

The NH₂ groups adopt trans orientations with respect to the mean fluorene plane. All amine H atoms participate in intermolecular hydrogen bonds (Table 2), although one of these (H71⋯O41) is very weak.

Figure 1
The molecular structure of (I

). Displacement ellipsoids are drawn at the 50% probability level.

Experimental

4,5-Dinitro-9-fluorenone-2,7-disulfonyl dichloride [(II); 200 mg, 0.43 mol] (Mysyk et al., 1997 ) was dissolved in dry dioxane (10 ml) and ammonia (35% solution in water, 0.2 ml) was added dropwise with intense stirring. The mixture was stirred at room temperature for 1 h and poured into water. The solid was filtered off, washed with warm water, dried and recrystallized from acetone, yielding pale yellow crystals of 4,5-dinitro-9-fluorenone-2,7-disulfonamide, (III) (130 mg, yield 71%, m.p. >573 K). ¹H NMR (400 MHz, acetone-d₆): δ 8.63 (2H, d, J = 1.5 Hz, H-3,6), 8.50 (2H, d, J = 1.5 Hz, H-1,8), 7.19 (4H, s, SO₂NH₂); ¹³C NMR (100 MHz, acetone-d₆): δ 186.56 (C=O), 149.28, 147.15, 139.40, 136.61, 128.86, 126.07. Analysis found: C 36.42, H 1.95, N 13.18, S 14.89%; C₁₃H₈N₄O₉S₂ requires: C 36.45, H 1.88, N 13.08, S 14.97%. Compound (III) (300 mg, 0.70 mmol) and malononitrile (100 mg, 167 mmol) in dimethylformamide (1.5 ml) were stirred at room temperature for 4 h and diluted with methanol (5 ml), resulting in precipitation. After keeping this solution at 273 K for 6 h, the solid obtained was filtered off and washed with water, yielding crude product (I) as a yellow–green solid. This was dissolved in a minimal amount of hot acetone and diluted with a fourfold volume of hot methanol. On cooling, a bright yellow solid was collected, washed with methanol and dried, giving 210 mg of (I) (yield 63%), m.p. >573 K. ¹H NMR (300 MHz, acetone-d₆ + ca 0.2 drop CF₃CO₂D): δ 9.36 (2H, d, J = 1.4 Hz, H-1.8), 8.71 (2H, d, J = 1.4 Hz, H-3,6), 7.32 (4H, s, SO₂NH₂). Analysis found: C 40.22, H 1.65, N 17.78, S 13.37; C₁₆H₈N₆O₈S₂ requires: C 40.34, H 1.69, N 17.64, S 13.46%. Single crystals of (I) of X-ray quality were obtained by slow evaporation (over several days) at room temperature of a solution of (I) (10 mg) in PhCl (10 ml) and acetonitrile (3 ml).

Crystal data

C₁₆H₈N₆O₈S₂
M_r = 476.40
Orthorhombic, Pna2₁
a = 9.574 (2) Å
b = 10.778 (6) Å
c = 17.461 (5) Å
V = 1801.8 (12) Å³
Z = 4
D_x = 1.756 Mg m⁻³
Cu Kα radiation
Cell parameters from 25 reflections
θ = 15.5–25.0°
μ = 3.30 mm⁻¹
T = 150 (2) K
Needle, yellow
0.45 × 0.06 × 0.05 mm

Data collection

Rigaku AFC-6S four-circle diffractometer
2θ/ω scans
Absorption correction: ψ scan (TEXSAN; Molecular Structure Corporation, 1989 ) T_min = 0.745, T_max = 0.848
2381 measured reflections
1942 independent reflections
1730 reflections with I > 2σ(I)
R_int = 0.033
θ_max = 75.1°
h = −1 → 12
k = −1 → 13
l = −1 → 21
3 standard reflections every 147 reflections intensity decay: 0.9%

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.106
S = 1.03
1942 reflections
199 parameters
H-atom parameters constrained
w = 1/[σ²(F_o²) + (0.06P)² + 0.7842P] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max < 0.001
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.43 e Å⁻³
Absolute structure: Flack (1983 )
Flack parameter = 0.01 (3)

Table 1
Selected geometric parameters (Å, °)

S2—O22	1.424 (4)
S2—O21	1.433 (4)
S2—N2	1.612 (4)
S2—C2	1.785 (5)
S7—O72	1.428 (4)
S7—O71	1.432 (3)
S7—N7	1.606 (4)
S7—C7	1.784 (5)
C1—C2	1.383 (7)
C1—C10	1.396 (6)
C2—C3	1.381 (7)
C3—C4	1.393 (6)
C4—C11	1.387 (7)
C4—N4	1.476 (6)
C5—C12	1.387 (6)
C5—C6	1.391 (6)
C5—N5	1.465 (6)
C6—C7	1.384 (6)
C7—C8	1.394 (6)
C8—C13	1.387 (7)
C9—C14	1.358 (6)
C9—C13	1.469 (6)
C9—C10	1.475 (6)
C10—C11	1.410 (6)
C11—C12	1.473 (6)
C12—C13	1.429 (6)
C14—C15	1.435 (6)
C14—C16	1.446 (7)
C15—N15	1.144 (7)
C16—N16	1.146 (7)
N4—O41	1.218 (5)
N4—O42	1.236 (5)
N5—O52	1.219 (5)
N5—O51	1.239 (5)

C2—C1—C10	117.7 (4)
C3—C2—C1	122.6 (4)
C3—C2—S2	117.4 (4)
C1—C2—S2	120.0 (4)
C2—C3—C4	118.2 (5)
C11—C4—C3	121.7 (4)
C11—C4—N4	122.2 (4)
C3—C4—N4	115.8 (4)
C12—C5—C6	122.6 (4)
C12—C5—N5	122.7 (4)
C6—C5—N5	114.5 (4)
C7—C6—C5	118.5 (4)
C6—C7—C8	121.9 (4)
C6—C7—S7	117.8 (3)
C8—C7—S7	120.2 (4)
C13—C8—C7	118.3 (4)
C14—C9—C13	125.9 (4)
C14—C9—C10	127.1 (4)
C13—C9—C10	106.8 (4)
C1—C10—C11	121.5 (4)
C1—C10—C9	130.4 (4)
C11—C10—C9	108.0 (4)
C4—C11—C10	117.4 (4)
C4—C11—C12	134.2 (4)
C10—C11—C12	108.3 (4)
C5—C12—C13	116.8 (4)
C5—C12—C11	135.2 (4)
C13—C12—C11	107.8 (4)
C8—C13—C12	121.7 (4)
C8—C13—C9	130.2 (4)
C12—C13—C9	107.9 (4)
C9—C14—C15	123.4 (4)
C9—C14—C16	122.2 (4)
C15—C14—C16	114.4 (4)

C1—C2—S2—N2	79.0 (4)
C8—C7—S7—N7	96.3 (4)

Table 2
Hydrogen-bonding geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H21⋯O72ⁱ	0.89	2.03	2.878 (6)	159
N2—H22⋯O52ⁱⁱ	0.89	2.10	2.925 (5)	153
N7—H71⋯O41ⁱⁱⁱ	0.89	2.51	3.116 (6)	126
N7—H72⋯N2^iv	0.89	2.24	3.103 (6)	162
Symmetry codes: (i) $[{\script{3\over 2}}-x,y-{\script{1\over 2}},{\script{1\over 2}}+z]$ ; (ii) x,y-1,z; (iii) $[1-x,2-y,z-{\script{1\over 2}}]$ ; (iv) $[1-x,1-y,z-{\script{1\over 2}}]$ .

Owing to an insufficient number of observed reflections, only the S, O and N atoms were refined with anisotropic displacement parameters, the C atoms being refined in isotropic approximation. Amine H atoms were refined in isotropic approximation, then constrained with the same bond direction but idealized N—H bond lengths (0.89 Å). Other H atoms were treated as riding in idealized positions, with C—H bond lengths of 0.95 Å and U_iso(H) = 1.2U_eq(C).

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1988 $[Molecular Structure Corporation (1988). MSC/AFC Diffractometer Control Software. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA.]$ ); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S160053680402361X/cv6380sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053680402361X/cv6380Isup2.hkl

Computing details top

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1988); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

9-Dicyanomethylene-4,5-dinitrofluorene-2,7-disulfonamide top

Crystal data top

C₁₆H₈N₆O₈S₂	D_x = 1.756 Mg m⁻³
M_r = 476.40	Melting point > 573 K
Orthorhombic, Pna2₁	Cu Kα radiation, λ = 1.54178 Å
a = 9.574 (2) Å	Cell parameters from 25 reflections
b = 10.778 (6) Å	θ = 15.5–25.0°
c = 17.461 (5) Å	µ = 3.30 mm⁻¹
V = 1801.8 (12) Å³	T = 150 K
Z = 4	Needle, yellow
F(000) = 968	0.45 × 0.06 × 0.05 mm

Data collection top

Rigaku AFC-6S four-circle diffractometer	1730 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.033
Graphite monochromator	θ_max = 75.1°, θ_min = 4.8°
2θ/ω scans	h = −1→12
Absorption correction: ψ scan (TEXSAN; Molecular Structure Corporation, 1989)	k = −1→13
T_min = 0.745, T_max = 0.848	l = −1→21
2381 measured reflections	3 standard reflections every 147 reflections
1942 independent reflections	intensity decay: 0.9%

Refinement top

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)] = 0.041	H-atom parameters constrained
wR(F²) = 0.106	w = 1/[σ²(F_o²) + (0.06P)² + 0.7842P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
1942 reflections	Δρ_max = 0.37 e Å⁻³
199 parameters	Δρ_min = −0.43 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 28 Friedel pairs [CHECK]
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.01 (3)

Special details top

Experimental. Needle-like crystal aligned approximately along the φ axis. 118 Friedel pairs has been measured.

exptl_absorpt_correction_type psi-scan (TEXSAN; Molecular Structure Corporation, 1989), on 108 ψ-scans of 3 reflections

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.

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

	x	y	z	U_iso*/U_eq
S2	0.32267 (12)	0.29279 (10)	0.30553 (7)	0.0227 (2)
S7	0.85953 (12)	0.95636 (10)	−0.00931 (7)	0.0214 (2)
C1	0.4962 (5)	0.4139 (4)	0.2047 (3)	0.0215 (9)*
H1	0.5019	0.3380	0.1773	0.026*
C2	0.4190 (5)	0.4233 (4)	0.2714 (3)	0.0212 (9)*
C3	0.4144 (5)	0.5305 (4)	0.3147 (3)	0.0248 (9)*
H3	0.3639	0.5331	0.3615	0.030*
C4	0.4858 (5)	0.6344 (4)	0.2879 (3)	0.0242 (10)*
C5	0.6182 (5)	0.8599 (4)	0.1692 (3)	0.0207 (9)*
C6	0.6941 (5)	0.9288 (4)	0.1162 (3)	0.0236 (10)*
H6	0.6960	1.0168	0.1187	0.028*
C7	0.7667 (5)	0.8662 (4)	0.0596 (3)	0.0185 (9)*
C8	0.7648 (5)	0.7372 (4)	0.0541 (3)	0.0213 (9)*
H8	0.8123	0.6958	0.0138	0.026*
C9	0.6638 (5)	0.5371 (4)	0.1149 (3)	0.0201 (9)*
C10	0.5655 (5)	0.5201 (4)	0.1790 (3)	0.0200 (9)*
C11	0.5517 (5)	0.6348 (4)	0.2171 (3)	0.0211 (9)*
C12	0.6193 (5)	0.7312 (4)	0.1702 (3)	0.0195 (9)*
C13	0.6921 (5)	0.6707 (4)	0.1093 (3)	0.0209 (9)*
C14	0.7247 (5)	0.4468 (4)	0.0721 (3)	0.0207 (9)*
C15	0.6810 (5)	0.3196 (4)	0.0736 (3)	0.0253 (10)*
C16	0.8411 (5)	0.4717 (5)	0.0216 (3)	0.0278 (10)*
N2	0.4291 (4)	0.1993 (4)	0.3479 (2)	0.0237 (9)
H21	0.4669	0.2361	0.3885	0.028*
H22	0.4937	0.1670	0.3171	0.028*
N4	0.4993 (4)	0.7382 (4)	0.3425 (2)	0.0272 (9)*
N5	0.5253 (4)	0.9336 (4)	0.2179 (2)	0.0276 (9)*
N7	0.7527 (4)	1.0028 (4)	−0.0741 (2)	0.0290 (9)
H71	0.7014	1.0593	−0.0498	0.035*
H72	0.7186	0.9356	−0.0971	0.035*
N15	0.6447 (5)	0.2185 (4)	0.0715 (3)	0.0365 (11)
N16	0.9357 (5)	0.4914 (4)	−0.0167 (3)	0.0386 (11)
O21	0.2300 (4)	0.3387 (3)	0.3634 (2)	0.0324 (8)
O22	0.2694 (4)	0.2294 (4)	0.2402 (2)	0.0374 (9)
O41	0.4083 (4)	0.7526 (4)	0.3904 (2)	0.0384 (9)
O42	0.6069 (4)	0.8012 (3)	0.3374 (2)	0.0328 (8)
O51	0.4081 (4)	0.8909 (3)	0.2326 (2)	0.0309 (8)
O52	0.5671 (4)	1.0355 (3)	0.2378 (2)	0.0405 (10)
O71	0.9091 (4)	1.0654 (3)	0.0289 (2)	0.0296 (8)
O72	0.9576 (4)	0.8737 (3)	−0.0438 (2)	0.0313 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S2	0.0195 (5)	0.0265 (5)	0.0222 (5)	−0.0038 (4)	−0.0003 (5)	0.0048 (5)
S7	0.0202 (5)	0.0226 (5)	0.0213 (5)	−0.0031 (4)	0.0013 (5)	−0.0003 (5)
N2	0.020 (2)	0.0255 (18)	0.025 (2)	0.0030 (15)	−0.0008 (17)	0.0011 (16)
N7	0.029 (2)	0.032 (2)	0.026 (2)	−0.0028 (17)	−0.0022 (19)	0.0052 (18)
N15	0.050 (3)	0.024 (2)	0.036 (3)	0.002 (2)	0.002 (2)	−0.0027 (18)
N16	0.037 (3)	0.033 (2)	0.046 (3)	0.0059 (19)	0.016 (2)	−0.002 (2)
O21	0.0257 (18)	0.0314 (18)	0.0402 (19)	0.0000 (15)	0.0115 (18)	0.0068 (16)
O22	0.041 (2)	0.042 (2)	0.0292 (19)	−0.0135 (18)	−0.0079 (18)	0.0041 (17)
O41	0.042 (2)	0.041 (2)	0.0321 (19)	−0.0055 (18)	0.0155 (18)	−0.0097 (18)
O42	0.033 (2)	0.0359 (18)	0.0297 (18)	−0.0071 (15)	−0.0014 (17)	−0.0050 (17)
O51	0.0259 (18)	0.0340 (18)	0.0327 (19)	0.0028 (15)	0.0033 (16)	−0.0009 (16)
O52	0.045 (2)	0.0264 (18)	0.050 (2)	−0.0054 (17)	0.020 (2)	−0.0156 (18)
O71	0.034 (2)	0.0239 (16)	0.0305 (18)	−0.0077 (15)	−0.0018 (17)	−0.0069 (15)
O72	0.0233 (17)	0.0338 (19)	0.0368 (19)	0.0021 (15)	0.0099 (18)	0.0034 (16)

Geometric parameters (Å, º) top

S2—O22	1.424 (4)	C7—C8	1.394 (6)
S2—O21	1.433 (4)	C8—C13	1.387 (7)
S2—N2	1.612 (4)	C8—H8	0.9500
S2—C2	1.785 (5)	C9—C14	1.358 (6)
S7—O72	1.428 (4)	C9—C13	1.469 (6)
S7—O71	1.432 (3)	C9—C10	1.475 (6)
S7—N7	1.606 (4)	C10—C11	1.410 (6)
S7—C7	1.784 (5)	C11—C12	1.473 (6)
C1—C2	1.383 (7)	C12—C13	1.429 (6)
C1—C10	1.396 (6)	C14—C15	1.435 (6)
C1—H1	0.9500	C14—C16	1.446 (7)
C2—C3	1.381 (7)	C15—N15	1.144 (7)
C3—C4	1.393 (6)	C16—N16	1.146 (7)
C3—H3	0.9499	N2—H21	0.8901
C4—C11	1.387 (7)	N2—H22	0.8900
C4—N4	1.476 (6)	N4—O41	1.218 (5)
C5—C12	1.387 (6)	N4—O42	1.236 (5)
C5—C6	1.391 (6)	N5—O52	1.219 (5)
C5—N5	1.465 (6)	N5—O51	1.239 (5)
C6—C7	1.384 (6)	N7—H71	0.8901
C6—H6	0.9500	N7—H72	0.8900

O22—S2—O21	120.6 (3)	C13—C8—H8	120.8
O22—S2—N2	107.1 (2)	C7—C8—H8	120.9
O21—S2—N2	106.5 (2)	C14—C9—C13	125.9 (4)
O22—S2—C2	107.2 (2)	C14—C9—C10	127.1 (4)
O21—S2—C2	106.5 (2)	C13—C9—C10	106.8 (4)
N2—S2—C2	108.6 (2)	C1—C10—C11	121.5 (4)
O72—S7—O71	119.4 (2)	C1—C10—C9	130.4 (4)
O72—S7—N7	108.4 (2)	C11—C10—C9	108.0 (4)
O71—S7—N7	106.5 (2)	C4—C11—C10	117.4 (4)
O72—S7—C7	105.8 (2)	C4—C11—C12	134.2 (4)
O71—S7—C7	107.3 (2)	C10—C11—C12	108.3 (4)
N7—S7—C7	109.1 (2)	C5—C12—C13	116.8 (4)
C2—C1—C10	117.7 (4)	C5—C12—C11	135.2 (4)
C2—C1—H1	121.2	C13—C12—C11	107.8 (4)
C10—C1—H1	121.2	C8—C13—C12	121.7 (4)
C3—C2—C1	122.6 (4)	C8—C13—C9	130.2 (4)
C3—C2—S2	117.4 (4)	C12—C13—C9	107.9 (4)
C1—C2—S2	120.0 (4)	C9—C14—C15	123.4 (4)
C2—C3—C4	118.2 (5)	C9—C14—C16	122.2 (4)
C2—C3—H3	120.8	C15—C14—C16	114.4 (4)
C4—C3—H3	121.0	N15—C15—C14	177.0 (6)
C11—C4—C3	121.7 (4)	N16—C16—C14	178.2 (6)
C11—C4—N4	122.2 (4)	S2—N2—H21	110.1
C3—C4—N4	115.8 (4)	S2—N2—H22	114.0
C12—C5—C6	122.6 (4)	H21—N2—H22	111.9
C12—C5—N5	122.7 (4)	O41—N4—O42	125.1 (4)
C6—C5—N5	114.5 (4)	O41—N4—C4	118.5 (4)
C7—C6—C5	118.5 (4)	O42—N4—C4	116.3 (4)
C7—C6—H6	120.6	O52—N5—O51	125.0 (4)
C5—C6—H6	120.8	O52—N5—C5	117.0 (4)
C6—C7—C8	121.9 (4)	O51—N5—C5	117.9 (4)
C6—C7—S7	117.8 (3)	S7—N7—H71	103.2
C8—C7—S7	120.2 (4)	S7—N7—H72	107.3
C13—C8—C7	118.3 (4)	H71—N7—H72	124.7

C1—C2—S2—N2	79.0 (4)	C8—C7—S7—N7	96.3 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H21···O72ⁱ	0.89	2.03	2.878 (6)	159
N2—H22···O52ⁱⁱ	0.89	2.10	2.925 (5)	153
N7—H71···O41ⁱⁱⁱ	0.89	2.51	3.116 (6)	126
N7—H72···N2^iv	0.89	2.24	3.103 (6)	162

Symmetry codes: (i) −x+3/2, y−1/2, z+1/2; (ii) x, y−1, z; (iii) −x+1, −y+2, z−1/2; (iv) −x+1, −y+1, z−1/2.

Acknowledgements

The authors thank Professor M. R. Bryce for fruitful advice. IFP thanks the Royal Society of Chemistry for an International Author grant.

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