organic papers
Acta Cryst.(2005). E61, o1121–o1122 doi:10.1107/S1600536805008706 Tufan Akbalet al. C
22H16N2O2S2
o1121
Acta Crystallographica Section E Structure Reports
Online
ISSN 1600-5368
4,5-Bis(3-methoxyphenylsulfanyl)phthalonitrile
Tufan Akbal,a* Nesuhi Akdemir,b Musa O¨ zil,bErbil Ag˘arband
Ahmet Erdo¨nmezb
aDepartment of Physics, Faculty of Arts and
Sciences, Ondokuz Mayıs University, TR-55139, Kurupelit-Samsun, Turkey, and
bDepartment of Chemistry, Faculty of Arts and
Sciences, Ondokuz Mayıs University, 55139 Samsun, Turkey
Correspondence e-mail: [email protected]
Key indicators
Single-crystal X-ray study T= 293 K
Mean(C–C) = 0.004 A˚ Rfactor = 0.051 wRfactor = 0.151
Data-to-parameter ratio = 19.7
For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.
#2005 International Union of Crystallography Printed in Great Britain – all rights reserved
In the title compound, C22H16N2O2S2, two benzene rings are
connected by a phthalonitrile moiety, the dihedral angle
between them being 47.9 (2). The crystal structure is
stabilized by intermolecular C—H N contacts.
Comment
Phthalonitriles are known precursors of phthalocyanines, an important class of molecules with wide applications (Leznoff & Lever, 1989–1996) ranging from catalysis to solid-state materials. Disubstituted phthalonitriles [e.g. 4,5-bis(3-methoxythiophenoxy)phthalonitrile] are generally used for synthesis of octasubstituted phthalocyanines (McKeown, 1998). For many years, phthalocyanines have attracted continued interest in various research fields, such as chemical
sensors, electrochromism, batteries, photosensitizers for
photodynamic cancer therapy, semiconductive materials, liquid crystals and non-linear optics (Leznoff & Lever, 1989– 1996).
The average value of C—N bond distances in the title compound, (I), (Table 1) indicates triple-bond character and it is consistent with the values observed in
4-(2-allylphenoxy)-phthalohalonitrile (Ko¨ysal et al., 2003a) and
4-(8-quinolinoxy)phthalohalonitrile (Ko¨ysal et al., 2003b). The O—C bond distances correspond to those in 4,40-(N
[image:1.610.264.398.393.498.2] [image:1.610.207.460.605.718.2]-phenyl-Received 20 December 2004 Accepted 17 March 2005 Online 25 March 2005
Figure 1
2,20-iminodiethanoxy)-diphthalonitrile (Ocaket al., 2003). The
three aromatic rings in the molecule are not coplanar. The dihedral angle between the C2–C7 and C16–C21 rings is 47.9 (2). These rings make dihedral angles of 61.61 (8)and
70.76 (9), respectively with the central aromatic ring. The two
methoxy groups are in ananti-orientation with respect to the central aromatic ring.
The crystal structure (Fig. 2) is stabilized by an inter-molecular contact C5—H5 N2i(i =x,y+ 1,z).
Experimental
3-methoxythiophenol (1.43 g, 10.20 mmol) and 4,5-dichlorophthalo-nitrile (1.00 g, 5.08 mmol) were dissolved in dry DMF (50 ml) with stirring under N2. Dry fine-powdered potassium carbonate (2.1 g,
15.21 mmol) was added in portions (101 mmol) every 10 min. The reaction mixture was stirred for 48 h at room temperature and poured into ice–water (150 g). The product was filtered off and washed with (10%w/w) NaOH solution and water until the filtrate was neutral. Recrystallization from ethanol gave a yellow product, yield 1.08 g (52.68%). Single crystals were obtained from ethyl acetate by slow evaporation at room temperature (m.p. 421 K); elemental analysis, calculated for C22H16N2O2S2: C 65.32, H 3.99, N 6.92%; found: C
65.28 H 3.90 N 6.96%.1H NMR (CDCl3) 3.86 p.p.m. (s, 3H, OCH3),
7.03–7.48 p.p.m. (m, 5H, Ar). 13C NMR (CDCl3) 55.50 (OCH3), 111.74, 115.36, 116.28, 120.23, 127.68, 129.68, 129.42, 130.12, 131.40, 144.03, 160.88.
Crystal data
C22H16N2O2S2
Mr= 404.49
Triclinic,P1 a= 7.8208 (11) A˚ b= 11.0356 (14) A˚ c= 11.5767 (15) A˚
= 91.531 (10)
= 102.391 (11)
= 91.567 (11) V= 975.0 (2) A˚3
Z= 2
Dx= 1.378 Mg m 3
MoKradiation
Cell parameters from 16920 reflections
= 2.5–28.6
= 0.29 mm1
T= 293 (2) K Prism, yellow 0.300.220.12 mm
Data collection
Stoe IPDS 2 diffractometer
!scans
Absorption correction: by integration (X-RED32; Stoe, 2002)
Tmin= 0.926,Tmax= 0.970 25939 measured reflections
4979 independent reflections 2390 reflections withI> 2(I) Rint= 0.084
max= 28.7
h=10!10 k=14!14 l=14!15
Refinement
Refinement onF2
R[F2> 2(F2)] = 0.051 wR(F2) = 0.151
S= 0.85 4979 reflections 253 parameters
H-atom parameters constrained w= 1/[2
(Fo2) + (0.0861P)2]
whereP= (Fo2+ 2Fc2)/3
(/)max< 0.001
max= 0.37 e A˚
3
min=0.37 e A˚
3
Table 1
Selected geometric parameters (A˚ ,).
C1—O1 1.406 (4)
C2—O1 1.361 (3)
C4—S1 1.775 (3)
C8—S1 1.759 (3)
C9—S2 1.755 (3)
C14—N2 1.141 (4)
C15—N1 1.146 (4)
C16—S2 1.780 (3)
C20—O2 1.360 (4)
C22—O2 1.422 (5)
C2—O1—C1 117.5 (2)
C20—O2—C22 117.6 (3)
C8—S1—C4 105.00 (13)
C9—S2—C16 104.28 (13)
C3—C2—O1—C1 6.0 (5)
C5—C4—S1—C8 51.8 (3)
[image:2.610.43.295.392.729.2]C17—C16—S2—C9 71.0 (3)
Table 2
Hydrogen-bonding geometry (A˚ ,).
D—H A D—H H A D A D—H A
C5—H5 N2i
0.93 2.56 3.493 (4) 177.9
Symmetry code: (i)x;1y;z.
H atoms were positioned geometrically and refined using a riding model, with aromatic C—H = 0.93 A˚ , other C—H = 0.96–0.97 A˚ and
Uiso(H) = 1.2 or 1.5 timesUeq(C).
Data collection:X-AREA(Stoe, 2002); cell refinement:X-AREA; data reduction: X-RED32 (Stoe, 2002); structure solution:
SHELXS97 (Sheldrick, 1997); structure refinement: SHELXL97
(Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication:
WinGX(Farrugia, 1999),PARST(Nardelli, 1995).
References
Burnett, M. N. & Johnson, C. K. (1996).ORTEPIII.Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.
Farrugia, L. J. (1999).J. Appl. Cryst.32, 837–838.
Ko¨ysal, Y., Isık S., Akdemir, N., Ag˘ar, E. & McKee, V. (2003a). E59, o1183– o1184.
Ko¨ysal, Y., Isık S., Akdemir, N., Ag˘ar, E. & McKee, V. (2003b). E59, o1423– o1424.
Leznoff, C. C. & Lever, A. B. P. (1989–1996).Phthalocyanines: Properties & Applications, Vols. 1,2,3 & 4. Weinheim & New York: VHC Publishers Inc. McKeown, N. B. (1998).Phthalocyanine Materials: Synthesis, Structure and
Function. Cambridge University Press. Nardelli, M. (1995).J. Appl. Cryst.28, 659.
Ocak, N., C¸ oruh, U., Akdemir, N., Kantar, C., Ag˘ar, E. & Erdo¨nmez, A. (2004).Acta Cryst.E60, o33–o34.
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Go¨ttingen, Germany.
Stoe (2002).X-AREA(Version 1.18) andX-RED32(Version 1.04). Stoe & Cie, Darmstadt, Germany.
supporting information
sup-1 Acta Cryst. (2005). E61, o1121–o1122
supporting information
Acta Cryst. (2005). E61, o1121–o1122 [https://doi.org/10.1107/S1600536805008706]
4,5-Bis(3-methoxyphenylsulfanyl)phthalonitrile
Tufan Akbal, Nesuhi Akdemir, Musa
Ö
zil, Erbil A
ğ
ar and Ahmet Erd
ö
nmez
4,5-Bis(3-methoxythiophenoxy)phthalonitrile
Crystal data
C22H16N2O2S2
Mr = 404.49 Triclinic, P1 Hall symbol: -P 1
a = 7.8208 (11) Å
b = 11.0356 (14) Å
c = 11.5767 (15) Å
α = 91.531 (10)°
β = 102.391 (11)°
γ = 91.567 (11)°
V = 975.0 (2) Å3
Z = 2
F(000) = 420
Dx = 1.378 Mg m−3
Mo Kα radiation, λ = 0.71073 Å Cell parameters from 16920 reflections
θ = 2.5–28.6°
µ = 0.29 mm−1
T = 293 K Prism, yellow
0.30 × 0.22 × 0.12 mm
Data collection
STOE IPDS 2 diffractometer
Radiation source: fine-focus sealed tube Graphite monochromator
Detector resolution: 6.67 pixels mm-1
ω scans
Absorption correction: integration X-RED32 (Stoe, 2002)
Tmin = 0.926, Tmax = 0.970
25939 measured reflections 4979 independent reflections 2390 reflections with I > 2σ(I)
Rint = 0.084
θmax = 28.7°, θmin = 2.5°
h = −10→10
k = −14→14
l = −14→15
Refinement
Refinement on F2 Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.051
wR(F2) = 0.151
S = 0.85 4979 reflections 253 parameters 0 restraints
Primary atom site location: structure-invariant direct methods
Secondary atom site location: difference Fourier map
Hydrogen site location: inferred from neighbouring sites
H-atom parameters constrained
w = 1/[σ2(F
o2) + (0.0861P)2] where P = (Fo2 + 2Fc2)/3 (Δ/σ)max < 0.001
Δρmax = 0.37 e Å−3 Δρmin = −0.37 e Å−3
Special details
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors 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.
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
x y z Uiso*/Ueq
C1 0.8781 (5) −0.0920 (4) 0.2293 (4) 0.0881 (12)
H1A 0.9590 −0.1553 0.2262 0.132*
H1B 0.8727 −0.0747 0.3101 0.132*
H1C 0.9166 −0.0203 0.1957 0.132*
C2 0.5790 (4) −0.0509 (2) 0.1593 (3) 0.0482 (6)
C3 0.6012 (4) 0.0672 (2) 0.2041 (2) 0.0474 (6)
H3 0.7118 0.0989 0.2401 0.057*
C4 0.4538 (4) 0.1376 (2) 0.1943 (2) 0.0487 (6)
C5 0.2901 (4) 0.0928 (3) 0.1404 (3) 0.0588 (8)
H5 0.1926 0.1401 0.1363 0.071*
C6 0.2726 (4) −0.0239 (3) 0.0924 (3) 0.0576 (8)
H6 0.1629 −0.0543 0.0531 0.069*
C7 0.4156 (4) −0.0956 (2) 0.1021 (3) 0.0538 (7)
H7 0.4020 −0.1743 0.0701 0.065*
C8 0.3794 (4) 0.3834 (2) 0.1655 (2) 0.0457 (6)
C9 0.3315 (4) 0.4937 (2) 0.2137 (2) 0.0460 (6)
C10 0.2514 (4) 0.5801 (2) 0.1379 (2) 0.0464 (6)
H10 0.2195 0.6526 0.1690 0.056*
C11 0.2184 (3) 0.5604 (2) 0.0175 (2) 0.0442 (6)
C12 0.2629 (3) 0.4507 (2) −0.0308 (2) 0.0451 (6)
C13 0.3425 (4) 0.3638 (2) 0.0444 (2) 0.0477 (6)
H13 0.3718 0.2908 0.0127 0.057*
C14 0.1372 (4) 0.6521 (2) −0.0581 (3) 0.0503 (7)
C15 0.2284 (4) 0.4308 (3) −0.1552 (3) 0.0544 (7)
C16 0.3268 (4) 0.6616 (2) 0.3976 (2) 0.0492 (7)
C17 0.4301 (4) 0.7570 (3) 0.3745 (3) 0.0578 (7)
H17 0.5242 0.7439 0.3389 0.069*
C18 0.3894 (5) 0.8732 (3) 0.4059 (3) 0.0616 (8)
H18 0.4556 0.9392 0.3893 0.074*
C19 0.2539 (4) 0.8922 (3) 0.4607 (3) 0.0592 (8)
H19 0.2289 0.9708 0.4814 0.071*
C20 0.1542 (4) 0.7957 (3) 0.4855 (3) 0.0535 (7)
C21 0.1880 (4) 0.6789 (3) 0.4526 (2) 0.0522 (7)
H21 0.1192 0.6134 0.4671 0.063*
C22 −0.0838 (5) 0.7287 (4) 0.5684 (4) 0.0919 (13)
H22A −0.1703 0.7611 0.6073 0.138*
H22B −0.0126 0.6741 0.6197 0.138*
H22C −0.1412 0.6858 0.4967 0.138*
N1 0.1987 (5) 0.4173 (3) −0.2561 (3) 0.1082 (10)
supporting information
sup-3 Acta Cryst. (2005). E61, o1121–o1122
O1 0.7109 (3) −0.12980 (18) 0.1645 (2) 0.0476 (6)
O2 0.0235 (3) 0.8251 (2) 0.5411 (2) 0.0578 (7)
S1 0.48939 (12) 0.28192 (7) 0.26827 (7) 0.0637 (3)
S2 0.37893 (13) 0.50926 (7) 0.36866 (7) 0.0635 (3)
Atomic displacement parameters (Å2)
U11 U22 U33 U12 U13 U23
C1 0.078 (3) 0.077 (2) 0.109 (3) 0.026 (2) 0.015 (2) −0.005 (2)
C2 0.0569 (17) 0.0422 (13) 0.0470 (15) 0.0100 (12) 0.0132 (13) 0.0033 (12)
C3 0.0550 (16) 0.0417 (13) 0.0454 (15) 0.0050 (12) 0.0102 (12) −0.0009 (11)
C4 0.0608 (17) 0.0390 (13) 0.0478 (16) 0.0090 (12) 0.0141 (13) 0.0032 (11)
C5 0.0536 (18) 0.0533 (16) 0.069 (2) 0.0107 (14) 0.0113 (15) 0.0011 (15)
C6 0.0564 (18) 0.0514 (16) 0.063 (2) −0.0037 (14) 0.0086 (15) −0.0007 (14)
C7 0.068 (2) 0.0387 (14) 0.0559 (18) −0.0006 (13) 0.0159 (15) 0.0000 (12)
C8 0.0499 (15) 0.0368 (12) 0.0497 (16) 0.0066 (11) 0.0092 (12) −0.0036 (11)
C9 0.0552 (16) 0.0390 (13) 0.0430 (15) 0.0050 (12) 0.0093 (12) −0.0043 (11)
C10 0.0569 (16) 0.0368 (12) 0.0445 (15) 0.0057 (12) 0.0088 (12) −0.0049 (11)
C11 0.0468 (15) 0.0390 (13) 0.0455 (15) 0.0008 (11) 0.0068 (12) 0.0012 (11)
C12 0.0460 (15) 0.0446 (14) 0.0438 (15) −0.0022 (11) 0.0091 (12) −0.0064 (11)
C13 0.0552 (16) 0.0392 (13) 0.0479 (16) 0.0054 (12) 0.0101 (13) −0.0087 (12)
C14 0.0531 (16) 0.0437 (14) 0.0506 (17) 0.0056 (12) 0.0028 (13) 0.0031 (13)
C15 0.0683 (19) 0.0537 (16) 0.0384 (16) 0.0003 (14) 0.0065 (14) −0.0077 (13)
C16 0.0659 (18) 0.0429 (14) 0.0372 (14) 0.0068 (13) 0.0075 (13) −0.0030 (11)
C17 0.0690 (19) 0.0563 (17) 0.0497 (17) −0.0031 (15) 0.0184 (15) −0.0072 (14)
C18 0.083 (2) 0.0496 (16) 0.0550 (19) −0.0083 (15) 0.0221 (17) −0.0076 (14)
C19 0.084 (2) 0.0418 (15) 0.0501 (17) 0.0050 (14) 0.0121 (16) −0.0087 (13)
C20 0.0655 (19) 0.0471 (15) 0.0477 (16) 0.0031 (14) 0.0119 (14) −0.0033 (12)
C21 0.0656 (18) 0.0452 (14) 0.0439 (16) −0.0031 (13) 0.0088 (13) −0.0037 (12)
C22 0.082 (3) 0.120 (3) 0.080 (3) 0.000 (2) 0.034 (2) −0.012 (2)
N1 0.135 (3) 0.111 (2) 0.075 (2) 0.0021 (19) 0.0148 (18) −0.0096 (17)
N2 0.104 (2) 0.0877 (19) 0.092 (2) 0.0189 (16) 0.0070 (16) 0.0108 (16)
O1 0.0472 (13) 0.0360 (11) 0.0572 (14) 0.0136 (9) 0.0056 (11) −0.0067 (10)
O2 0.0590 (15) 0.0517 (13) 0.0718 (17) 0.0035 (11) 0.0352 (13) −0.0096 (12)
S1 0.0893 (6) 0.0429 (4) 0.0517 (5) 0.0213 (4) −0.0026 (4) −0.0060 (3)
S2 0.1019 (7) 0.0450 (4) 0.0415 (4) 0.0198 (4) 0.0095 (4) −0.0033 (3)
Geometric parameters (Å, º)
C1—O1 1.406 (4) C11—C12 1.404 (3)
C1—H1A 0.9600 C11—C14 1.427 (4)
C1—H1B 0.9600 C12—C13 1.381 (4)
C1—H1C 0.9600 C12—C15 1.417 (4)
C2—O1 1.361 (3) C13—H13 0.9300
C2—C7 1.378 (4) C14—N2 1.141 (4)
C2—C3 1.382 (4) C15—N1 1.146 (4)
C3—C4 1.394 (4) C16—C17 1.376 (4)
C4—C5 1.371 (4) C16—S2 1.780 (3)
C4—S1 1.775 (3) C17—C18 1.387 (4)
C5—C6 1.379 (4) C17—H17 0.9300
C5—H5 0.9300 C18—C19 1.366 (4)
C6—C7 1.374 (4) C18—H18 0.9300
C6—H6 0.9300 C19—C20 1.376 (4)
C7—H7 0.9300 C19—H19 0.9300
C8—C13 1.380 (4) C20—O2 1.360 (4)
C8—C9 1.419 (3) C20—C21 1.383 (4)
C8—S1 1.759 (3) C21—H21 0.9300
C9—C10 1.382 (4) C22—O2 1.422 (5)
C9—S2 1.755 (3) C22—H22A 0.9600
C10—C11 1.373 (4) C22—H22B 0.9600
C10—H10 0.9300 C22—H22C 0.9600
O1—C1—H1A 109.5 C13—C12—C11 119.1 (2)
O1—C1—H1B 109.5 C13—C12—C15 120.9 (2)
H1A—C1—H1B 109.5 C11—C12—C15 120.0 (3)
O1—C1—H1C 109.5 C8—C13—C12 121.2 (2)
H1A—C1—H1C 109.5 C8—C13—H13 119.4
H1B—C1—H1C 109.5 C12—C13—H13 119.4
O1—C2—C7 115.2 (2) N2—C14—C11 178.1 (3)
O1—C2—C3 124.4 (3) N1—C15—C12 178.5 (3)
C7—C2—C3 120.4 (2) C17—C16—C21 121.9 (3)
C2—C3—C4 118.4 (3) C17—C16—S2 120.6 (2)
C2—C3—H3 120.8 C21—C16—S2 117.3 (2)
C4—C3—H3 120.8 C16—C17—C18 117.9 (3)
C5—C4—C3 121.6 (3) C16—C17—H17 121.0
C5—C4—S1 122.5 (2) C18—C17—H17 121.0
C3—C4—S1 115.6 (2) C19—C18—C17 121.1 (3)
C4—C5—C6 118.8 (3) C19—C18—H18 119.5
C4—C5—H5 120.6 C17—C18—H18 119.5
C6—C5—H5 120.6 C18—C19—C20 120.3 (3)
C7—C6—C5 120.7 (3) C18—C19—H19 119.9
C7—C6—H6 119.6 C20—C19—H19 119.9
C5—C6—H6 119.6 O2—C20—C19 115.3 (3)
C6—C7—C2 120.1 (3) O2—C20—C21 124.5 (3)
C6—C7—H7 120.0 C19—C20—C21 120.2 (3)
C2—C7—H7 120.0 C20—C21—C16 118.6 (3)
C13—C8—C9 119.4 (2) C20—C21—H21 120.7
C13—C8—S1 124.68 (19) C16—C21—H21 120.7
C9—C8—S1 115.9 (2) O2—C22—H22A 109.5
C10—C9—C8 119.2 (2) O2—C22—H22B 109.5
C10—C9—S2 124.66 (19) H22A—C22—H22B 109.5
C8—C9—S2 116.2 (2) O2—C22—H22C 109.5
C11—C10—C9 120.9 (2) H22A—C22—H22C 109.5
C11—C10—H10 119.5 H22B—C22—H22C 109.5
supporting information
sup-5 Acta Cryst. (2005). E61, o1121–o1122
C10—C11—C12 120.3 (2) C20—O2—C22 117.6 (3)
C10—C11—C14 119.4 (2) C8—S1—C4 105.00 (13)
C12—C11—C14 120.3 (3) C9—S2—C16 104.28 (13)
O1—C2—C3—C4 −179.0 (3) C11—C12—C13—C8 −0.3 (4)
C7—C2—C3—C4 2.5 (4) C15—C12—C13—C8 178.8 (3)
C2—C3—C4—C5 −0.8 (4) C21—C16—C17—C18 −1.3 (5)
C2—C3—C4—S1 173.3 (2) S2—C16—C17—C18 −175.9 (2)
C3—C4—C5—C6 −1.7 (5) C16—C17—C18—C19 1.6 (5)
S1—C4—C5—C6 −175.3 (2) C17—C18—C19—C20 −0.3 (5)
C4—C5—C6—C7 2.4 (5) C18—C19—C20—O2 179.5 (3)
C5—C6—C7—C2 −0.6 (5) C18—C19—C20—C21 −1.5 (5)
O1—C2—C7—C6 179.5 (3) O2—C20—C21—C16 −179.3 (3)
C3—C2—C7—C6 −1.9 (4) C19—C20—C21—C16 1.8 (4)
C13—C8—C9—C10 −1.0 (4) C17—C16—C21—C20 −0.4 (4)
S1—C8—C9—C10 177.2 (2) S2—C16—C21—C20 174.4 (2)
C13—C8—C9—S2 178.6 (2) C7—C2—O1—C1 −175.5 (3)
S1—C8—C9—S2 −3.2 (3) C3—C2—O1—C1 6.0 (5)
C8—C9—C10—C11 −0.1 (4) C19—C20—O2—C22 179.8 (3)
S2—C9—C10—C11 −179.7 (2) C21—C20—O2—C22 0.9 (5)
C9—C10—C11—C12 1.1 (4) C13—C8—S1—C4 −24.4 (3)
C9—C10—C11—C14 −179.3 (3) C9—C8—S1—C4 157.4 (2)
C10—C11—C12—C13 −0.9 (4) C5—C4—S1—C8 −51.8 (3)
C14—C11—C12—C13 179.5 (3) C3—C4—S1—C8 134.2 (2)
C10—C11—C12—C15 180.0 (3) C10—C9—S2—C16 −7.0 (3)
C14—C11—C12—C15 0.4 (4) C8—C9—S2—C16 173.4 (2)
C9—C8—C13—C12 1.2 (4) C17—C16—S2—C9 −71.0 (3)
S1—C8—C13—C12 −176.9 (2) C21—C16—S2—C9 114.1 (2)
Hydrogen-bond geometry (Å, º)
D—H···A D—H H···A D···A D—H···A
C5—H5···N2i 0.93 2.56 3.493 (4) 178
