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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2011 Aug 17;67(Pt 9):o2359. doi: 10.1107/S1600536811032284

1-Benzyl-2,5-diphenyl-3-tosylimidazol­idin-4-one

K Sakthimurugesan a, S Ranjith a, A SubbiahPandi a,*, K Namitharan b, K Pitchumani b
PMCID: PMC3200849  PMID: 22058970

Abstract

In the title compound, C29H26N2O3S, the central imidazolidine ring adopts an envelope conformation with the N atom bearing the benzyl ring at the flap. The S atom has distorted tetra­hedral geometry. The benzyl and tosyl rings are oriented at a dihedral angle of 52.1 (1)°. The phenyl rings connected to the imidazolidine ring form a dihedral angle of 28.7 (1)°.

Related literature

For the biological activity of sulfonamides, see: Zareef et al. (2007 ▶); Chohan & Shad (2007 ▶); Pomarnacka & Kozlarska-Kedra (2003 ▶); Nieto et al. (2005 ▶); Wang et al. (1995 ▶). For a related structure, see: Ranjith et al. (2011 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶). For asymmetry parameters, see: Nardelli et al. (1983 ▶).graphic file with name e-67-o2359-scheme1.jpg

Experimental

Crystal data

  • C29H26N2O3S

  • M r = 482.58

  • Monoclinic, Inline graphic

  • a = 18.6024 (7) Å

  • b = 8.0489 (3) Å

  • c = 17.0860 (6) Å

  • β = 106.426 (2)°

  • V = 2453.85 (16) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.17 mm−1

  • T = 293 K

  • 0.25 × 0.22 × 0.19 mm

Data collection

  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.981, T max = 0.985

  • 25449 measured reflections

  • 4805 independent reflections

  • 3598 reflections with I > 2σ(I)

  • R int = 0.032

Refinement

  • R[F 2 > 2σ(F 2)] = 0.039

  • wR(F 2) = 0.115

  • S = 1.01

  • 4805 reflections

  • 317 parameters

  • H-atom parameters constrained

  • Δρmax = 0.15 e Å−3

  • Δρmin = −0.38 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811032284/ci5194sup1.cif

e-67-o2359-sup1.cif (24KB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811032284/ci5194Isup2.hkl

e-67-o2359-Isup2.hkl (230.6KB, hkl)

Supplementary material file. DOI: 10.1107/S1600536811032284/ci5194Isup3.cml

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

Acknowledgments

SR and ASP thank Dr Babu Varghese, SAIF, IIT, Chennai, India, for the data collection.

supplementary crystallographic information

Comment

Sulfonamides have widely been recognized for their wide variety of pharmacological activities such as antibacterial, antitumor, anti-carbonic anhydrase, diuretic, hypoglycaemic, antithyroid and protease inhibitory activity. Sulfonamides, particularly sulfadiazine and sulfadoxine, have also been used clinically as antimalarial agents (Zareef et al., 2007). Due to their significant pharmacological applications and widespread use in medicine, these compounds have also gained attention in bioinorganic and metal-based drug chemistry (Chohan et al., 2007). Sulfonamide derivatives are well known drugs and are used to control diseases caused by bacterial infections. Benzene sulfonamide derivatives are known to exhibit anticancer and HIV activities (Pomarnacka & Kozlarska-Kedra, 2003) and antibacterial activities (Nieto et al., 2005). Imidazolidine compounds are important intermediates and building blocks in the construction of various biologically active compounds (Wang et al., 1995). Against this background, and in order to obtain detailed information on molecular conformations in the solid state, an X-ray study of the title compound was carried out.

X-Ray analysis confirms the molecular structure and atom connectivity as illustrated in Fig. 1. The geometry around the S atom is distorted tetrahedral, with a O1—S1—O2 angle of 120.5 (1)°. The widening of this angle may be due to repulsive interactions between the two short S═O bonds, similar to that observed in a related structure (Ranjith et al., 2011). The S—O, S—C and S–N distances are comparable to those observed in similar structures (Ranjith et al., 2011). The methyl atom C1 deviates by 0.021 (3) Å from the plane of the C2–C7 ring.

The imidazolidine ring adopts an envelope conformation, with the puckering parameters q2 and φ (Cremer & Pople, 1975) and the smallest displacement asymmetric parameters, Δ, (Nardelli et al., 1983) as follows: q2 = 0.302 (2) Å, φ = 257.1 (3)° and Δs(N2) = 3.3 (2)°. The methylbenzene ring (C2–C7) makes dihedral angles of 43.6 (1), 52.1 (1) and 72.3 (1)° with respect to the C9–C14, C16–C21 and C24–C29 benzene rings.

The molecules lack hydrogen bonding functionality. The crystal packing is stabilized by van der Waals interactions.

Experimental

Alkyne (1 mmol) in dichloromethane (1 ml) was added slowly to a mixture of CuI-zeolite (30 mg), 4-toluene sulfonyl azide (1 mmol), N-benzylnitrone (1 mmol) and triethylamine (1.2 mmol) in dichloromethane (2 ml) under N2 atmosphere. After stirring at room temperature for the 3 h, the mixture was diluted with dichloromethane. After removing the catalyst by filtration, followed by solvent evaporation under reduced pressure, the resulting crude product was finally purified by column chromatography on silica gel (60–120 mesh) with ethyl acetate and petroleum ether as eluting solvent to give the desired product. Single crystals suitable for X-ray diffraction were obtained by slow evaporation of a solution of the title compound in acetone at room temperature.

Refinement

H atoms were positioned geometrically [C–H = 0.93–0.97 Å] and allowed to ride on their parent C atoms, with Uiso(H) = 1.2Ueq(C) [1.5Ueq(C) for methyl H atoms].

Figures

Fig. 1.

Fig. 1.

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The molecular structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.

Crystal data

C29H26N2O3S F(000) = 1016
Mr = 482.58 Dx = 1.306 Mg m−3
Monoclinic, P21/c Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc Cell parameters from 4805 reflections
a = 18.6024 (7) Å θ = 1.1–26.0°
b = 8.0489 (3) Å µ = 0.17 mm−1
c = 17.0860 (6) Å T = 293 K
β = 106.426 (2)° Block, white crystalline
V = 2453.85 (16) Å3 0.25 × 0.22 × 0.19 mm
Z = 4
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Data collection

Bruker APEXII CCD area-detector diffractometer 4805 independent reflections
Radiation source: fine-focus sealed tube 3598 reflections with I > 2σ(I)
graphite Rint = 0.032
ω and φ scans θmax = 26.0°, θmin = 1.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) h = −22→20
Tmin = 0.981, Tmax = 0.985 k = −9→8
25449 measured reflections l = −20→21
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Refinement

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)] = 0.039 Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115 H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0556P)2 + 0.6284P] where P = (Fo2 + 2Fc2)/3
4805 reflections (Δ/σ)max = 0.001
317 parameters Δρmax = 0.15 e Å−3
0 restraints Δρmin = −0.38 e Å−3
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Special details

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

x y z Uiso*/Ueq
C1 0.59892 (15) 1.1019 (4) 0.3124 (2) 0.1139 (11)
H1A 0.6361 1.1075 0.3644 0.171*
H1B 0.5989 1.2039 0.2833 0.171*
H1C 0.6103 1.0111 0.2814 0.171*
C2 0.52227 (12) 1.0751 (3) 0.32515 (14) 0.0663 (6)
C3 0.45945 (13) 1.1508 (3) 0.27587 (14) 0.0714 (6)
H3 0.4644 1.2209 0.2344 0.086*
C4 0.38964 (11) 1.1257 (3) 0.28613 (12) 0.0584 (5)
H4 0.3478 1.1777 0.2519 0.070*
C5 0.38237 (9) 1.0228 (2) 0.34764 (10) 0.0421 (4)
C6 0.44422 (10) 0.9453 (2) 0.39808 (12) 0.0548 (5)
H6 0.4393 0.8750 0.4395 0.066*
C7 0.51360 (11) 0.9735 (3) 0.38628 (14) 0.0665 (6)
H7 0.5556 0.9223 0.4207 0.080*
C8 0.23093 (9) 0.6933 (2) 0.36626 (10) 0.0414 (4)
H8 0.1928 0.7370 0.3904 0.050*
C9 0.29247 (9) 0.6072 (2) 0.43025 (10) 0.0453 (4)
C10 0.34796 (11) 0.5227 (3) 0.40738 (12) 0.0576 (5)
H10 0.3475 0.5206 0.3528 0.069*
C11 0.40383 (12) 0.4417 (3) 0.46466 (15) 0.0739 (6)
H11 0.4412 0.3853 0.4491 0.089*
C12 0.40401 (15) 0.4446 (3) 0.54519 (15) 0.0843 (7)
H12 0.4423 0.3919 0.5843 0.101*
C13 0.34830 (16) 0.5244 (3) 0.56805 (14) 0.0809 (7)
H13 0.3480 0.5234 0.6224 0.097*
C14 0.29260 (12) 0.6062 (3) 0.51072 (11) 0.0614 (5)
H14 0.2549 0.6611 0.5265 0.074*
C15 0.14866 (9) 0.4518 (2) 0.31824 (11) 0.0435 (4)
H15A 0.1747 0.4021 0.3702 0.052*
H15B 0.1417 0.3655 0.2771 0.052*
C16 0.07241 (9) 0.50676 (19) 0.32246 (10) 0.0405 (4)
C17 0.05947 (11) 0.5553 (2) 0.39499 (12) 0.0544 (5)
H17 0.0989 0.5565 0.4427 0.065*
C18 −0.01143 (12) 0.6018 (3) 0.39741 (14) 0.0649 (6)
H18 −0.0192 0.6350 0.4465 0.078*
C19 −0.07037 (11) 0.5994 (2) 0.32768 (14) 0.0617 (5)
H19 −0.1181 0.6298 0.3295 0.074*
C20 −0.05838 (10) 0.5521 (2) 0.25558 (13) 0.0580 (5)
H20 −0.0981 0.5513 0.2081 0.070*
C21 0.01189 (10) 0.5057 (2) 0.25284 (12) 0.0489 (4)
H21 0.0191 0.4730 0.2034 0.059*
C22 0.16901 (9) 0.6743 (2) 0.22488 (10) 0.0419 (4)
H22 0.1195 0.7190 0.2229 0.050*
C23 0.22466 (9) 0.8161 (2) 0.23794 (11) 0.0455 (4)
C24 0.16290 (10) 0.5747 (2) 0.14846 (10) 0.0451 (4)
C25 0.11035 (13) 0.6192 (3) 0.07717 (12) 0.0692 (6)
H25 0.0789 0.7093 0.0766 0.083*
C26 0.10414 (17) 0.5299 (4) 0.00611 (14) 0.0879 (8)
H26 0.0685 0.5605 −0.0419 0.105*
C27 0.14972 (16) 0.3984 (3) 0.00633 (15) 0.0830 (7)
H27 0.1455 0.3393 −0.0415 0.100*
C28 0.20162 (15) 0.3530 (3) 0.07650 (16) 0.0812 (7)
H28 0.2328 0.2627 0.0766 0.097*
C29 0.20811 (12) 0.4407 (3) 0.14747 (13) 0.0638 (5)
H29 0.2436 0.4086 0.1953 0.077*
N1 0.25830 (8) 0.82623 (17) 0.32174 (8) 0.0452 (3)
N2 0.19719 (7) 0.58031 (16) 0.29956 (8) 0.0404 (3)
O1 0.24894 (7) 1.13491 (17) 0.32774 (10) 0.0749 (5)
O2 0.30718 (8) 0.97342 (18) 0.45167 (8) 0.0668 (4)
O3 0.23762 (7) 0.90679 (16) 0.18789 (8) 0.0610 (4)
S1 0.29541 (2) 1.00278 (5) 0.36717 (3) 0.04955 (15)
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Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
C1 0.0717 (17) 0.137 (3) 0.153 (3) −0.0412 (18) 0.0645 (18) −0.059 (2)
C2 0.0541 (13) 0.0747 (14) 0.0762 (14) −0.0185 (11) 0.0283 (11) −0.0283 (12)
C3 0.0761 (16) 0.0759 (15) 0.0662 (13) −0.0238 (13) 0.0269 (12) 0.0004 (11)
C4 0.0532 (12) 0.0566 (11) 0.0588 (11) −0.0067 (10) 0.0050 (9) 0.0084 (9)
C5 0.0362 (9) 0.0389 (9) 0.0485 (9) −0.0027 (7) 0.0077 (7) −0.0069 (7)
C6 0.0466 (11) 0.0569 (11) 0.0574 (11) 0.0054 (9) 0.0092 (9) 0.0047 (9)
C7 0.0393 (11) 0.0765 (15) 0.0769 (14) 0.0085 (10) 0.0051 (10) −0.0123 (12)
C8 0.0348 (9) 0.0426 (9) 0.0487 (9) −0.0014 (7) 0.0146 (7) −0.0042 (7)
C9 0.0392 (9) 0.0472 (10) 0.0470 (9) −0.0033 (8) 0.0082 (7) −0.0025 (8)
C10 0.0475 (11) 0.0686 (13) 0.0538 (11) 0.0074 (10) 0.0096 (9) −0.0021 (9)
C11 0.0531 (13) 0.0760 (15) 0.0832 (16) 0.0162 (11) 0.0038 (11) −0.0034 (12)
C12 0.0822 (18) 0.0794 (16) 0.0699 (15) 0.0139 (14) −0.0134 (13) 0.0098 (13)
C13 0.0952 (19) 0.0859 (17) 0.0519 (12) 0.0079 (15) 0.0053 (12) 0.0054 (11)
C14 0.0642 (13) 0.0693 (13) 0.0499 (11) 0.0030 (11) 0.0149 (9) −0.0016 (9)
C15 0.0391 (9) 0.0359 (8) 0.0534 (10) −0.0006 (7) 0.0097 (8) 0.0023 (7)
C16 0.0370 (9) 0.0321 (8) 0.0520 (9) −0.0033 (7) 0.0120 (7) 0.0029 (7)
C17 0.0485 (11) 0.0609 (11) 0.0540 (11) −0.0055 (9) 0.0146 (9) 0.0009 (9)
C18 0.0650 (14) 0.0648 (13) 0.0769 (14) −0.0025 (11) 0.0398 (12) −0.0036 (11)
C19 0.0440 (11) 0.0486 (11) 0.0983 (16) 0.0030 (9) 0.0293 (11) 0.0086 (11)
C20 0.0384 (10) 0.0512 (11) 0.0783 (14) −0.0009 (9) 0.0064 (9) 0.0082 (10)
C21 0.0425 (10) 0.0461 (10) 0.0562 (10) −0.0024 (8) 0.0109 (8) −0.0001 (8)
C22 0.0349 (9) 0.0414 (9) 0.0485 (9) 0.0004 (7) 0.0104 (7) 0.0013 (7)
C23 0.0390 (9) 0.0422 (9) 0.0546 (10) 0.0013 (8) 0.0119 (8) 0.0022 (8)
C24 0.0425 (10) 0.0457 (10) 0.0483 (9) −0.0075 (8) 0.0147 (8) −0.0016 (8)
C25 0.0835 (16) 0.0604 (13) 0.0554 (12) 0.0079 (12) 0.0060 (11) −0.0002 (10)
C26 0.114 (2) 0.0915 (19) 0.0479 (12) −0.0014 (16) 0.0059 (13) −0.0045 (12)
C27 0.110 (2) 0.0846 (18) 0.0618 (14) −0.0159 (16) 0.0372 (14) −0.0192 (13)
C28 0.0861 (17) 0.0805 (16) 0.0884 (17) 0.0104 (14) 0.0433 (14) −0.0187 (13)
C29 0.0532 (12) 0.0716 (13) 0.0679 (13) 0.0111 (11) 0.0192 (10) −0.0088 (11)
N1 0.0424 (8) 0.0405 (8) 0.0512 (8) −0.0072 (6) 0.0109 (6) −0.0030 (6)
N2 0.0346 (7) 0.0390 (7) 0.0455 (7) −0.0026 (6) 0.0079 (6) −0.0006 (6)
O1 0.0429 (8) 0.0440 (8) 0.1284 (13) 0.0088 (6) 0.0087 (8) −0.0106 (8)
O2 0.0708 (10) 0.0728 (9) 0.0662 (9) −0.0216 (8) 0.0346 (7) −0.0267 (7)
O3 0.0617 (9) 0.0556 (8) 0.0642 (8) −0.0102 (7) 0.0153 (7) 0.0122 (7)
S1 0.0380 (3) 0.0413 (3) 0.0695 (3) −0.00206 (19) 0.0156 (2) −0.0123 (2)
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Geometric parameters (Å, °)

C1—C2 1.517 (3) C15—H15B 0.97
C1—H1A 0.96 C16—C17 1.384 (2)
C1—H1B 0.96 C16—C21 1.388 (2)
C1—H1C 0.96 C17—C18 1.383 (3)
C2—C7 1.372 (3) C17—H17 0.93
C2—C3 1.375 (3) C18—C19 1.372 (3)
C3—C4 1.374 (3) C18—H18 0.93
C3—H3 0.93 C19—C20 1.367 (3)
C4—C5 1.375 (2) C19—H19 0.93
C4—H4 0.93 C20—C21 1.373 (3)
C5—C6 1.377 (2) C20—H20 0.93
C5—S1 1.7492 (17) C21—H21 0.93
C6—C7 1.380 (3) C22—N2 1.448 (2)
C6—H6 0.93 C22—C24 1.509 (2)
C7—H7 0.93 C22—C23 1.514 (2)
C8—N2 1.454 (2) C22—H22 0.98
C8—N1 1.484 (2) C23—O3 1.199 (2)
C8—C9 1.510 (2) C23—N1 1.393 (2)
C8—H8 0.98 C24—C29 1.370 (3)
C9—C14 1.374 (2) C24—C25 1.376 (3)
C9—C10 1.382 (3) C25—C26 1.387 (3)
C10—C11 1.374 (3) C25—H25 0.93
C10—H10 0.93 C26—C27 1.356 (4)
C11—C12 1.375 (3) C26—H26 0.93
C11—H11 0.93 C27—C28 1.360 (3)
C12—C13 1.367 (4) C27—H27 0.93
C12—H12 0.93 C28—C29 1.379 (3)
C13—C14 1.376 (3) C28—H28 0.93
C13—H13 0.93 C29—H29 0.93
C14—H14 0.93 N1—S1 1.6719 (14)
C15—N2 1.466 (2) O1—S1 1.4152 (14)
C15—C16 1.507 (2) O2—S1 1.4176 (15)
C15—H15A 0.97
C2—C1—H1A 109.5 C21—C16—C15 120.25 (15)
C2—C1—H1B 109.5 C18—C17—C16 120.81 (18)
H1A—C1—H1B 109.5 C18—C17—H17 119.6
C2—C1—H1C 109.5 C16—C17—H17 119.6
H1A—C1—H1C 109.5 C19—C18—C17 120.31 (19)
H1B—C1—H1C 109.5 C19—C18—H18 119.8
C7—C2—C3 117.91 (19) C17—C18—H18 119.8
C7—C2—C1 120.8 (2) C20—C19—C18 119.51 (18)
C3—C2—C1 121.3 (2) C20—C19—H19 120.2
C4—C3—C2 121.8 (2) C18—C19—H19 120.2
C4—C3—H3 119.1 C19—C20—C21 120.41 (19)
C2—C3—H3 119.1 C19—C20—H20 119.8
C3—C4—C5 119.14 (19) C21—C20—H20 119.8
C3—C4—H4 120.4 C20—C21—C16 121.24 (18)
C5—C4—H4 120.4 C20—C21—H21 119.4
C4—C5—C6 120.42 (17) C16—C21—H21 119.4
C4—C5—S1 119.85 (14) N2—C22—C24 113.86 (14)
C6—C5—S1 119.54 (14) N2—C22—C23 101.65 (13)
C5—C6—C7 118.97 (19) C24—C22—C23 114.16 (14)
C5—C6—H6 120.5 N2—C22—H22 109.0
C7—C6—H6 120.5 C24—C22—H22 109.0
C2—C7—C6 121.7 (2) C23—C22—H22 109.0
C2—C7—H7 119.1 O3—C23—N1 125.08 (16)
C6—C7—H7 119.1 O3—C23—C22 128.34 (16)
N2—C8—N1 100.60 (12) N1—C23—C22 106.56 (14)
N2—C8—C9 110.56 (13) C29—C24—C25 118.58 (18)
N1—C8—C9 113.73 (13) C29—C24—C22 122.18 (16)
N2—C8—H8 110.5 C25—C24—C22 119.24 (17)
N1—C8—H8 110.5 C24—C25—C26 120.2 (2)
C9—C8—H8 110.5 C24—C25—H25 119.9
C14—C9—C10 119.34 (17) C26—C25—H25 119.9
C14—C9—C8 120.91 (16) C27—C26—C25 120.3 (2)
C10—C9—C8 119.70 (15) C27—C26—H26 119.8
C11—C10—C9 120.48 (19) C25—C26—H26 119.8
C11—C10—H10 119.8 C26—C27—C28 120.0 (2)
C9—C10—H10 119.8 C26—C27—H27 120.0
C10—C11—C12 119.5 (2) C28—C27—H27 120.0
C10—C11—H11 120.3 C27—C28—C29 120.1 (2)
C12—C11—H11 120.3 C27—C28—H28 119.9
C13—C12—C11 120.4 (2) C29—C28—H28 119.9
C13—C12—H12 119.8 C24—C29—C28 120.8 (2)
C11—C12—H12 119.8 C24—C29—H29 119.6
C12—C13—C14 120.1 (2) C28—C29—H29 119.6
C12—C13—H13 120.0 C23—N1—C8 111.42 (13)
C14—C13—H13 120.0 C23—N1—S1 122.21 (12)
C9—C14—C13 120.2 (2) C8—N1—S1 122.10 (11)
C9—C14—H14 119.9 C22—N2—C8 109.39 (12)
C13—C14—H14 119.9 C22—N2—C15 117.95 (12)
N2—C15—C16 116.69 (13) C8—N2—C15 115.24 (13)
N2—C15—H15A 108.1 O1—S1—O2 120.51 (10)
C16—C15—H15A 108.1 O1—S1—N1 107.54 (8)
N2—C15—H15B 108.1 O2—S1—N1 104.82 (8)
C16—C15—H15B 108.1 O1—S1—C5 108.26 (9)
H15A—C15—H15B 107.3 O2—S1—C5 108.96 (8)
C17—C16—C21 117.71 (17) N1—S1—C5 105.81 (7)
C17—C16—C15 122.02 (16)
C7—C2—C3—C4 −0.6 (3) C23—C22—C24—C25 −91.4 (2)
C1—C2—C3—C4 179.1 (2) C29—C24—C25—C26 −0.4 (3)
C2—C3—C4—C5 0.3 (3) C22—C24—C25—C26 179.6 (2)
C3—C4—C5—C6 −0.3 (3) C24—C25—C26—C27 0.0 (4)
C3—C4—C5—S1 174.68 (16) C25—C26—C27—C28 0.3 (4)
C4—C5—C6—C7 0.5 (3) C26—C27—C28—C29 −0.1 (4)
S1—C5—C6—C7 −174.51 (15) C25—C24—C29—C28 0.5 (3)
C3—C2—C7—C6 0.8 (3) C22—C24—C29—C28 −179.43 (19)
C1—C2—C7—C6 −178.9 (2) C27—C28—C29—C24 −0.3 (4)
C5—C6—C7—C2 −0.7 (3) O3—C23—N1—C8 −178.77 (16)
N2—C8—C9—C14 −126.54 (18) C22—C23—N1—C8 2.63 (18)
N1—C8—C9—C14 121.16 (18) O3—C23—N1—S1 24.0 (2)
N2—C8—C9—C10 51.0 (2) C22—C23—N1—S1 −154.56 (11)
N1—C8—C9—C10 −61.3 (2) N2—C8—N1—C23 16.44 (17)
C14—C9—C10—C11 −1.6 (3) C9—C8—N1—C23 134.65 (15)
C8—C9—C10—C11 −179.11 (19) N2—C8—N1—S1 173.67 (10)
C9—C10—C11—C12 0.3 (3) C9—C8—N1—S1 −68.13 (17)
C10—C11—C12—C13 1.3 (4) C24—C22—N2—C8 155.71 (13)
C11—C12—C13—C14 −1.7 (4) C23—C22—N2—C8 32.47 (16)
C10—C9—C14—C13 1.2 (3) C24—C22—N2—C15 −69.98 (18)
C8—C9—C14—C13 178.72 (19) C23—C22—N2—C15 166.78 (13)
C12—C13—C14—C9 0.4 (4) N1—C8—N2—C22 −30.57 (15)
N2—C15—C16—C17 −92.39 (19) C9—C8—N2—C22 −151.07 (13)
N2—C15—C16—C21 89.38 (19) N1—C8—N2—C15 −166.24 (13)
C21—C16—C17—C18 −0.4 (3) C9—C8—N2—C15 73.27 (17)
C15—C16—C17—C18 −178.65 (17) C16—C15—N2—C22 −56.7 (2)
C16—C17—C18—C19 0.5 (3) C16—C15—N2—C8 75.00 (18)
C17—C18—C19—C20 −0.6 (3) C23—N1—S1—O1 37.22 (16)
C18—C19—C20—C21 0.6 (3) C8—N1—S1—O1 −117.56 (14)
C19—C20—C21—C16 −0.5 (3) C23—N1—S1—O2 166.60 (13)
C17—C16—C21—C20 0.4 (3) C8—N1—S1—O2 11.81 (15)
C15—C16—C21—C20 178.67 (16) C23—N1—S1—C5 −78.31 (15)
N2—C22—C23—O3 160.73 (18) C8—N1—S1—C5 126.91 (13)
C24—C22—C23—O3 37.7 (2) C4—C5—S1—O1 −15.47 (17)
N2—C22—C23—N1 −20.73 (16) C6—C5—S1—O1 159.54 (14)
C24—C22—C23—N1 −143.77 (15) C4—C5—S1—O2 −148.21 (15)
N2—C22—C24—C29 −27.6 (2) C6—C5—S1—O2 26.80 (17)
C23—C22—C24—C29 88.6 (2) C4—C5—S1—N1 99.56 (15)
N2—C22—C24—C25 152.48 (17) C6—C5—S1—N1 −85.43 (15)
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Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI5194).

References

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Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811032284/ci5194sup1.cif

e-67-o2359-sup1.cif (24KB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811032284/ci5194Isup2.hkl

e-67-o2359-Isup2.hkl (230.6KB, hkl)

Supplementary material file. DOI: 10.1107/S1600536811032284/ci5194Isup3.cml

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

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography

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