Fluoren-9-one 4-toluene­sulfonyl­hydrazone: hydrogen-bonded R{_2^2}(8) dimers are linked into sheets by π–π stacking interactions

Glidewell, C.; Low, J.N.; Skakle, J.M.S.; Wardell, J.L.

doi:10.1107/S1600536804004878

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 60| Part 4| April 2004| Pages o520-o522

https://doi.org/10.1107/S1600536804004878

Fluoren-9-one 4-toluenesulfonylhydrazone: hydrogen-bonded R $[{_2^2}]$ (8) dimers are linked into sheets by π–π stacking interactions

Christopher Glidewell,^a ^* John N. Low,^b Janet M. S. Skakle ^b and James L. Wardell ^c

^aSchool of Chemistry, University of St Andrews, St Andrews, Fife KY16 9ST, Scotland, ^bDepartment of Chemistry, University of Aberdeen, Meston Walk, Old Aberdeen AB24 3UE, Scotland, and ^cInstituto de Química, Departamento de Química Inorgânica, Universidade Federal do Rio de Janeiro, 21945-970 Rio de Janeiro-RJ, Brazil
^*Correspondence e-mail: cg@st-andrews.ac.uk

(Received 1 March 2004; accepted 2 March 2004; online 13 March 2004)

Molecules of the title compound, C₂₀H₁₆N₂O₂S, are linked into centrosymmetric R $[{_2^2}]$ (8) dimers by paired N—H⋯O hydrogen bonds [H⋯O 2.14 Å, N⋯O 2.9951 (15) Å and N—H⋯O 164°]. Two distinct π–π stacking interactions link the dimers into chains along [10 $[\overline 1]$ ] and [001], respectively, hence forming (010) sheets.

Comment

4-Toluenesulfonylhydrazones, R¹R²C=NNHC₆H₄Me, are not only important derivatives of carbonyl compounds, R¹R²C=O, but are also very useful precursors of diazo compounds, R¹R²CN₂, (Jonczyk & Wlostowska, 1978 ), as exemplified by the title compound, (I) (Fig. 1).

The molecules of (I) are linked by paired N—H⋯O=S hydrogen bonds into centrosymmetric dimers, with the reference dimer centred at ( $[{1 \over 2}]$ , $[{1 \over 2}]$ , $[{1 \over 2}]$ ) (Fig. 2). The associated R $[{_2^2}]$ (8) (Bernstein et al., 1995 ) motif has been observed previously in a number of sulfonamido species (Klug, 1968 ; Blaschette et al., 1986 ; Tremayne et al., 1999 , 2002 ; Kelly et al., 2002 ; Clark et al., 2003 ). While there are no soft hydrogen bonds of either C—H⋯O or C—H⋯π(arene) types present in the structure of (I), the dimeric aggregates are linked into sheets by two distinct π–π stacking interactions, one involving aryl rings and the other involving the fulvene portion of the fluorenone hydrazone.

The C11–C16 aryl rings of the molecules at (x, y, z) and (2 − x, 1 − y, −z) are parallel, with an interplanar spacing of 3.427 (2) Å; the centroid separation is 3.725 (2) Å, corresponding to a centroid offset of 1.460 (2) Å. These two molecules lie in the R $[{_2^2}]$ (8) dimers centred at ( $[{1 \over 2}]$ , $[{1 \over 2}]$ , $[{1 \over 2}]$ ) and ( $[{3 \over 2}]$ , $[{1 \over 2}]$ , − $[{1 \over 2}]$ ), respectively, so that propagation by inversion of this π–π interaction generates a chain of π-stacked dimers running parallel to the [10 $[\overline 1]$ ] direction (Fig. 3).

The fulvene-type rings (C7/C11/C16/C26/C21) of the molecules at (x, y, z) and (1 − x, 1 − y, −z), which lie in the R $[{_2^2}]$ (8) dimers centred at ( $[{1 \over 2}]$ , $[{1 \over 2}]$ , $[{1 \over 2}]$ ) and ( $[{1 \over 2}]$ , $[{1 \over 2}]$ , − $[{1 \over 2}]$ ), respectively, are also parallel; the interplanar spacing is 3.419 (2) Å and the centroid separation is 3.451 (2) Å, corresponding to a centroid offset of only 0.473 (2) Å. Propagation by inversion of the interaction generates a second chain of π-stacked dimers, in this case running parallel to the [001] direction (Fig. 4). The combination of the [001] and [10 $[\overline 1]$ ] chains generates an (010) sheet.

Figure 1
The molecule of (I

), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.

Figure 2
Part of the crystal structure of (I

), showing the formation of an R $[{_2^2}]$ (8) dimer. For the sake of clarity, H atoms bonded to C atoms have been omitted. The atoms marked with an asterisk (*) are at the symmetry position (1 − x, 1 − y, 1 − z).

Figure 3
A stereoview of part of the crystal structure of (I

), showing the formation of a [10 $[\overline 1]$ ] chain of π-stacked dimers. For the sake of clarity, H atoms bonded to C atoms have been omitted.

Figure 4
A stereoview of part of the crystal structure of (I

), showing the formation of an [001] chain of π-stacked dimers. For the sake of clarity, H atoms bonded to C atoms have been omitted.

Experimental

The title compound was prepared using the published procedure of Bamford & Stevens (1952 ) and it was recrystallized from ethanol [m.p. 457–460 K (decomposes); literature m.p. 453–455 K (decomposes)].

Crystal data

C₂₀H₁₆N₂O₂S
M_r = 348.41
Triclinic, $[P\overline 1]$
a = 7.7487 (2) Å
b = 10.4290 (3) Å
c = 11.2007 (3) Å
α = 71.8482 (13)°
β = 76.9553 (17)°
γ = 75.3167 (17)°
V = 821.34 (4) Å³
Z = 2
D_x = 1.409 Mg m⁻³
Mo Kα radiation
Cell parameters from 3744 reflections
θ = 3.1–27.5°
μ = 0.21 mm⁻¹
T = 120 (2) K
Block, yellow
0.48 × 0.40 × 0.26 mm

Data collection

Nonius KappaCCD area-detector diffractometer
φ scans, and ω scans with κ offsets
Absorption correction: multi-scan (SORTAV; Blessing, 1995 , 1997 ) T_min = 0.915, T_max = 0.947
6955 measured reflections
3744 independent reflections
3294 reflections with I > 2σ(I)
R_int = 0.016
θ_max = 27.5°
h = −9 → 10
k = −13 → 13
l = −14 → 14

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.090
S = 1.06
3744 reflections
227 parameters
H-atom parameters constrained
w = 1/[σ²(F_o²) + (0.0355P)² + 0.4642P] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max < 0.001
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.49 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

S1—C1	1.7569 (13)
S1—O1	1.4281 (10)
S1—O2	1.4448 (10)
S1—N8	1.6375 (11)
N8—N7	1.4038 (16)
N7—C7	1.2916 (18)
C7—C11	1.4803 (19)
C7—C21	1.485 (2)
C11—C16	1.403 (2)
C21—C26	1.4140 (19)
C16—C26	1.467 (2)

C11—C7—N7—N8	178.55 (11)
C7—N7—N8—S1	169.89 (9)

Table 2
Hydrogen-bonding geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N8—H8⋯O2ⁱ	0.88	2.14	2.9951 (15)	164
Symmetry code: (i) 1-x,1-y,1-z.

All H atoms were located using difference maps and subsequently treated as riding atoms, with C—H distances of 0.95 (aromatic) or 0.98 (methyl), and an N—H distance of 0.88 Å, and with U_iso(H) = 1.2U_eq(C,N), or 1.5U_eq(C) for methyl H.

Data collection: KappaCCD Server Software (Nonius, 1997 ); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 ); data reduction: DENZO-SMN; program(s) used to solve structure: OSCAIL (McArdle, 2003 ) and SHELXS86 (Sheldrick, 1990 ); program(s) used to refine structure: OSCAIL and SHELXL97 (Sheldrick, 1997 ); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536804004878/lh6178sup1.cif

Structure factors: contains datablock 478. DOI: https://doi.org/10.1107/S1600536804004878/lh6178Isup2.hkl

Computing details top

Data collection: KappaCCD Server Software (Nonius, 1997); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: OSCAIL (McArdle, 2003) and SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: OSCAIL and SHELXS97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999).

Fluoren-9-one 4-toluenesulfonylhydrazone top

Crystal data top

C₂₀H₁₆N₂O₂S	Z = 2
M_r = 348.41	F(000) = 364
Triclinic, P1	D_x = 1.409 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.7487 (2) Å	Cell parameters from 3744 reflections
b = 10.4290 (3) Å	θ = 3.1–27.5°
c = 11.2007 (3) Å	µ = 0.21 mm⁻¹
α = 71.8482 (13)°	T = 120 K
β = 76.9553 (17)°	Block, yellow
γ = 75.3167 (17)°	0.48 × 0.40 × 0.26 mm
V = 821.34 (4) Å³

Data collection top

Nonius KappaCCD area-detector diffractometer	3744 independent reflections
Radiation source: rotating anode	3294 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.016
φ scans, and ω scans with κ offsets	θ_max = 27.5°, θ_min = 3.1°
Absorption correction: multi-scan (SORTAV; Blessing, 1995, 1997)	h = −9→10
T_min = 0.915, T_max = 0.947	k = −13→13
6955 measured reflections	l = −14→14

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.090	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0355P)² + 0.4642P] where P = (F_o² + 2F_c²)/3
3744 reflections	(Δ/σ)_max < 0.001
227 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.49 e Å⁻³

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

	x	y	z	U_iso*/U_eq
S1	0.49758 (4)	0.29627 (3)	0.46935 (3)	0.01486 (10)
O1	0.42730 (13)	0.19893 (10)	0.43797 (9)	0.0200 (2)
O2	0.38541 (13)	0.37025 (10)	0.55813 (9)	0.0191 (2)
N7	0.65778 (15)	0.37426 (12)	0.24099 (11)	0.0175 (2)
N8	0.53735 (15)	0.41975 (12)	0.34037 (10)	0.0170 (2)
C1	0.70124 (18)	0.21206 (14)	0.52723 (12)	0.0152 (3)
C2	0.72736 (19)	0.07160 (14)	0.58536 (13)	0.0190 (3)
C3	0.8796 (2)	0.00832 (15)	0.64325 (14)	0.0213 (3)
C4	1.00559 (19)	0.08295 (15)	0.64246 (13)	0.0198 (3)
C5	0.97835 (19)	0.22305 (15)	0.58033 (14)	0.0201 (3)
C6	0.82650 (19)	0.28867 (14)	0.52338 (13)	0.0192 (3)
C7	0.66885 (18)	0.46685 (14)	0.13309 (13)	0.0173 (3)
C11	0.79401 (19)	0.43389 (15)	0.02076 (13)	0.0203 (3)
C12	0.9210 (2)	0.31646 (16)	0.01045 (15)	0.0253 (3)
C13	1.0248 (2)	0.31484 (19)	−0.10839 (16)	0.0313 (4)
C14	0.9996 (2)	0.42802 (19)	−0.21281 (15)	0.0317 (4)
C15	0.8723 (2)	0.54628 (18)	−0.20293 (14)	0.0278 (3)
C16	0.7699 (2)	0.54903 (16)	−0.08441 (13)	0.0214 (3)
C21	0.57250 (19)	0.61144 (15)	0.08941 (13)	0.0184 (3)
C22	0.44142 (19)	0.69726 (15)	0.15144 (14)	0.0215 (3)
C23	0.3761 (2)	0.83030 (16)	0.08245 (15)	0.0264 (3)
C24	0.4379 (2)	0.87671 (16)	−0.04685 (15)	0.0273 (3)
C25	0.5645 (2)	0.79084 (16)	−0.11100 (14)	0.0253 (3)
C26	0.63292 (19)	0.65890 (15)	−0.04260 (13)	0.0203 (3)
C41	1.1667 (2)	0.01449 (17)	0.70916 (15)	0.0280 (3)
H12	0.9371	0.2391	0.0822	0.030*
H13	1.1135	0.2355	−0.1180	0.038*
H14	1.0713	0.4245	−0.2930	0.038*
H15	0.8556	0.6231	−0.2751	0.033*
H22	0.3971	0.6657	0.2396	0.026*
H23	0.2878	0.8904	0.1244	0.032*
H24	0.3927	0.9685	−0.0919	0.033*
H25	0.6037	0.8218	−0.2000	0.030*
H8	0.5552	0.4929	0.3555	0.020*
H2	0.6427	0.0196	0.5856	0.023*
H3	0.8979	−0.0876	0.6841	0.026*
H5	1.0654	0.2745	0.5770	0.024*
H6	0.8082	0.3845	0.4823	0.023*
H41A	1.1328	0.0129	0.7993	0.042*
H41B	1.2642	0.0659	0.6700	0.042*
H41C	1.2081	−0.0800	0.7017	0.042*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.01527 (17)	0.01553 (17)	0.01290 (16)	−0.00454 (12)	−0.00134 (12)	−0.00203 (12)
O1	0.0209 (5)	0.0209 (5)	0.0208 (5)	−0.0083 (4)	−0.0036 (4)	−0.0055 (4)
O2	0.0182 (5)	0.0195 (5)	0.0177 (5)	−0.0023 (4)	0.0001 (4)	−0.0057 (4)
N7	0.0174 (6)	0.0213 (6)	0.0156 (6)	−0.0056 (5)	−0.0013 (4)	−0.0068 (5)
N8	0.0211 (6)	0.0172 (6)	0.0123 (5)	−0.0051 (5)	−0.0002 (4)	−0.0040 (4)
C1	0.0158 (6)	0.0170 (6)	0.0120 (6)	−0.0024 (5)	−0.0014 (5)	−0.0041 (5)
C2	0.0207 (7)	0.0172 (7)	0.0185 (7)	−0.0060 (5)	−0.0013 (5)	−0.0035 (5)
C3	0.0232 (7)	0.0162 (7)	0.0204 (7)	−0.0020 (5)	−0.0024 (5)	−0.0013 (5)
C4	0.0184 (7)	0.0231 (7)	0.0158 (6)	−0.0004 (5)	−0.0017 (5)	−0.0061 (5)
C5	0.0179 (7)	0.0223 (7)	0.0222 (7)	−0.0056 (5)	−0.0027 (5)	−0.0077 (6)
C6	0.0191 (7)	0.0157 (6)	0.0214 (7)	−0.0037 (5)	−0.0019 (5)	−0.0039 (5)
C7	0.0169 (6)	0.0236 (7)	0.0148 (6)	−0.0088 (5)	−0.0021 (5)	−0.0062 (5)
C11	0.0194 (7)	0.0303 (8)	0.0166 (7)	−0.0134 (6)	0.0001 (5)	−0.0091 (6)
C12	0.0237 (8)	0.0294 (8)	0.0271 (8)	−0.0099 (6)	−0.0009 (6)	−0.0124 (6)
C13	0.0261 (8)	0.0402 (9)	0.0369 (9)	−0.0141 (7)	0.0053 (7)	−0.0244 (8)
C14	0.0332 (9)	0.0482 (10)	0.0236 (8)	−0.0243 (8)	0.0089 (6)	−0.0199 (7)
C15	0.0323 (8)	0.0419 (9)	0.0162 (7)	−0.0235 (7)	0.0027 (6)	−0.0092 (6)
C16	0.0228 (7)	0.0317 (8)	0.0155 (7)	−0.0163 (6)	−0.0013 (5)	−0.0069 (6)
C21	0.0192 (7)	0.0244 (7)	0.0148 (6)	−0.0109 (6)	−0.0038 (5)	−0.0037 (5)
C22	0.0221 (7)	0.0260 (7)	0.0172 (7)	−0.0065 (6)	−0.0042 (5)	−0.0049 (6)
C23	0.0270 (8)	0.0266 (8)	0.0278 (8)	−0.0044 (6)	−0.0090 (6)	−0.0079 (6)
C24	0.0326 (8)	0.0249 (8)	0.0263 (8)	−0.0088 (6)	−0.0146 (6)	0.0000 (6)
C25	0.0300 (8)	0.0326 (8)	0.0168 (7)	−0.0172 (7)	−0.0072 (6)	−0.0002 (6)
C26	0.0216 (7)	0.0296 (8)	0.0142 (6)	−0.0153 (6)	−0.0033 (5)	−0.0038 (6)
C41	0.0237 (8)	0.0295 (8)	0.0274 (8)	−0.0006 (6)	−0.0092 (6)	−0.0032 (6)

Geometric parameters (Å, º) top

S1—C1	1.7569 (13)	C22—H22	0.95
S1—O1	1.4281 (10)	C23—C24	1.389 (2)
S1—O2	1.4448 (10)	C23—H23	0.95
S1—N8	1.6375 (11)	C24—C25	1.385 (2)
N8—N7	1.4038 (16)	C24—H24	0.95
N7—C7	1.2916 (18)	C25—C26	1.385 (2)
C11—C12	1.381 (2)	C25—H25	0.95
C7—C11	1.4803 (19)	N8—H8	0.88
C7—C21	1.485 (2)	C1—C2	1.3876 (19)
C11—C16	1.403 (2)	C1—C6	1.3911 (19)
C21—C26	1.4140 (19)	C2—C3	1.390 (2)
C16—C26	1.467 (2)	C2—H2	0.95
C12—C13	1.394 (2)	C3—C4	1.392 (2)
C12—H12	0.95	C3—H3	0.95
C13—C14	1.388 (3)	C4—C5	1.393 (2)
C13—H13	0.95	C4—C41	1.504 (2)
C14—C15	1.388 (3)	C5—C6	1.385 (2)
C14—H14	0.95	C5—H5	0.95
C15—C16	1.389 (2)	C6—H6	0.95
C15—H15	0.95	C41—H41A	0.98
C21—C22	1.387 (2)	C41—H41B	0.98
C22—C23	1.390 (2)	C41—H41C	0.98

C12—C11—C16	121.46 (13)	N7—C7—C21	133.19 (13)
C12—C11—C7	130.27 (14)	C11—C7—C21	106.51 (12)
C16—C11—C7	108.25 (13)	C7—N7—N8	114.54 (12)
C11—C12—C13	118.00 (15)	N7—N8—S1	114.07 (9)
C11—C12—H12	121.0	N7—N8—H8	116.2
C13—C12—H12	121.0	S1—N8—H8	113.6
C14—C13—C12	120.60 (16)	O1—S1—O2	118.82 (6)
C14—C13—H13	119.7	O1—S1—N8	108.85 (6)
C12—C13—H13	119.7	O2—S1—N8	102.95 (6)
C13—C14—C15	121.61 (14)	O1—S1—C1	108.45 (6)
C13—C14—H14	119.2	O2—S1—C1	108.17 (6)
C15—C14—H14	119.2	N8—S1—C1	109.26 (6)
C14—C15—C16	118.02 (15)	C2—C1—C6	121.17 (13)
C14—C15—H15	121.0	C2—C1—S1	119.07 (10)
C16—C15—H15	121.0	C6—C1—S1	119.55 (10)
C15—C16—C11	120.29 (15)	C1—C2—C3	118.80 (13)
C15—C16—C26	130.92 (15)	C1—C2—H2	120.6
C11—C16—C26	108.77 (12)	C3—C2—H2	120.6
C22—C21—C26	119.77 (13)	C2—C3—C4	121.18 (13)
C22—C21—C7	132.65 (13)	C2—C3—H3	119.4
C26—C21—C7	107.54 (12)	C4—C3—H3	119.4
C21—C22—C23	118.84 (14)	C3—C4—C5	118.73 (13)
C21—C22—H22	120.6	C3—C4—C41	120.79 (13)
C23—C22—H22	120.6	C5—C4—C41	120.48 (13)
C24—C23—C22	121.00 (15)	C6—C5—C4	121.09 (13)
C24—C23—H23	119.5	C6—C5—H5	119.5
C22—C23—H23	119.5	C4—C5—H5	119.5
C25—C24—C23	120.84 (14)	C5—C6—C1	119.00 (13)
C25—C24—H24	119.6	C5—C6—H6	120.5
C23—C24—H24	119.6	C1—C6—H6	120.5
C26—C25—C24	118.57 (14)	C4—C41—H41A	109.5
C26—C25—H25	120.7	C4—C41—H41B	109.5
C24—C25—H25	120.7	H41A—C41—H41B	109.5
C25—C26—C21	120.93 (14)	C4—C41—H41C	109.5
C25—C26—C16	130.19 (13)	H41A—C41—H41C	109.5
C21—C26—C16	108.88 (13)	H41B—C41—H41C	109.5
N7—C7—C11	120.27 (13)

C16—C11—C12—C13	−0.4 (2)	C12—C11—C7—C21	176.23 (14)
C7—C11—C12—C13	−178.44 (13)	C16—C11—C7—C21	−2.00 (14)
C11—C12—C13—C14	−0.4 (2)	C22—C21—C7—N7	2.4 (3)
C12—C13—C14—C15	0.4 (2)	C26—C21—C7—N7	−175.65 (14)
C13—C14—C15—C16	0.3 (2)	C22—C21—C7—C11	−179.86 (14)
C14—C15—C16—C11	−1.1 (2)	C26—C21—C7—C11	2.13 (14)
C14—C15—C16—C26	176.96 (14)	C11—C7—N7—N8	178.55 (11)
C12—C11—C16—C15	1.2 (2)	C21—C7—N7—N8	−3.9 (2)
C7—C11—C16—C15	179.58 (12)	C7—N7—N8—S1	169.89 (9)
C12—C11—C16—C26	−177.29 (12)	N7—N8—S1—O1	−57.89 (10)
C7—C11—C16—C26	1.13 (15)	N7—N8—S1—O2	175.17 (9)
C26—C21—C22—C23	−1.9 (2)	N7—N8—S1—C1	60.38 (10)
C7—C21—C22—C23	−179.72 (14)	O1—S1—C1—C2	−27.20 (13)
C21—C22—C23—C24	1.1 (2)	O2—S1—C1—C2	102.92 (11)
C22—C23—C24—C25	1.0 (2)	N8—S1—C1—C2	−145.71 (11)
C23—C24—C25—C26	−2.1 (2)	O1—S1—C1—C6	158.00 (11)
C24—C25—C26—C21	1.3 (2)	O2—S1—C1—C6	−71.89 (12)
C24—C25—C26—C16	−178.06 (14)	N8—S1—C1—C6	39.49 (12)
C22—C21—C26—C25	0.8 (2)	C6—C1—C2—C3	1.7 (2)
C7—C21—C26—C25	179.07 (12)	S1—C1—C2—C3	−173.04 (10)
C22—C21—C26—C16	−179.79 (12)	C1—C2—C3—C4	−0.7 (2)
C7—C21—C26—C16	−1.48 (15)	C2—C3—C4—C5	−1.1 (2)
C15—C16—C26—C25	1.4 (3)	C2—C3—C4—C41	177.93 (13)
C11—C16—C26—C25	179.61 (14)	C3—C4—C5—C6	1.9 (2)
C15—C16—C26—C21	−178.00 (14)	C41—C4—C5—C6	−177.11 (13)
C11—C16—C26—C21	0.23 (15)	C4—C5—C6—C1	−0.9 (2)
C12—C11—C7—N7	−5.6 (2)	C2—C1—C6—C5	−0.9 (2)
C16—C11—C7—N7	176.12 (12)	S1—C1—C6—C5	173.81 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N8—H8···O2ⁱ	0.88	2.14	2.9951 (15)	164

Symmetry code: (i) −x+1, −y+1, −z+1.

Acknowledgements

X-ray data were collected at the EPSRC X-ray Crystallographic Service, University of Southampton, UK; the authors thank the staff for all their help and advice. JNL thanks NCR Self-Service, Dundee, for grants which have provided computing facilities for this work. JLW thanks CNPq and FAPERJ for financial support.

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