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In crystals of the title compound, C23H23N5O3S, the indole system is planar and the phenyl ring of the phenylsulfonyl group makes a dihedral angle with the best plane of the indole system of 77.18 (4)°. The olefinic bond connecting the aza­bicyclic and indole systems has Z geometry. The geometry adopted by the C=O bond with respect to the N-N bond is trans. The O atom of the carbonyl group of each mol­ecule is hydrogen bonded to the hydrazidic H atom of an adjacent mol­ecule to form an eight-membered-ring dimeric structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270107006129/hj3030sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270107006129/hj3030Isup2.hkl
Contains datablock I

CCDC reference: 649082

Comment top

Radiotherapy is the treatment of cancer and other diseases with ionizing radiation. The technique is successful because ionizing radiation kills dividing cells and is thus slightly more toxic to fast-growing cancer cells than to normal cells. Radiotherapy may be used to treat localized solid tumours, such as cancers of the skin, tongue, larynx, brain, breast, uterus or cervix. Agents which are used to potentiate the effectiveness of radiation therapy in destroying unwanted cells are radio-sensitizing agents. Recently, we have reported (Sekhar et al., 2007) the radio-sensitizing activity of N-arylsubstituted (Z)-(±)-2-(1H-indol-3-ylmethylene)-1-azabicyclo[2.2.2]octan-3-ols. Systematic structural modification of the active molecule (Z)-2-(1-phenylsulfonyl-1H-indol-3-ylmethylene)-1-azabicyclo[2.2.2]octan-3-one, (II), was carried out and the title compound, (I), was synthesized as a structural analogue of (II). In order to confirm the double-bond geometry, and to determine the molecular conformation in the crystal structure, the X-ray crystallographic analysis of (I) has been carried out and the results are presented here.

X-ray crystallography confirmed the molecular structure and atom connectivity for (I), as illustrated in Fig. 1. Selected geometric parameters are presented in Table 1. The indole ring is planar, with bond distances and angles comparable with those previously reported for other indole derivatives (Mason et al., 2003; Zarza, et al., 1988).

In compound (I), atom N1 lies only very slightly [0.0555 (15) Å] out of the plane of the connecting atoms S1, C1 and C8, the sum of the angles about N1 being 359.58 (11)°. In a previous study, 21 structurally related indole analogues bearing N-arylsulphonate groupings were analyzed (Beddoes et al., 1986) (available in the Cambridge Structural Database; Allen, 2002), and the sums of the three angles around the N atom were determined, to assess planarity. It was found that only two of the 21 compounds had values that were outside the range 359.0–360°, the farthest value from the perfectly planar situation being 357.2°. This is in general agreement with our current observation with compound (I). However, it should be noted that in at least one case, i.e. in a moiety consisting of a pyrrolidine N atom bearing a toluene sulfonyl group, atom N1 can exist significantly out of the plane of the connecting atoms S1, C1 and C4 (335.1°), indicating pyrimidalization at the N atom (Helliwell et al., 1997).

The sulfonyl group of (I) has a distorted tetrahedral geometry, with widening of the O2—S1—O3 angle [120.99 (7)°] and the resultant narrowing of the N1—S1—C18 angle [104.88 (7)°] from ideal tetrahedral values. This type of deviation in the sulfonyl group has been reported previously (Beddoes et al., 1994; Govindasamy et al., 1998; Zhao et al., 1997, 1999), and is due to the repulsive interaction between the short S O bonds. The S—O, S—C and S—N distances are comparable with those found in N-phenylsulfonamides (Gomes et al., 1993). The orientation of the phenylsulfonyl group with respect to the planar indole moiety [r.m.s. deviation = 0.0172 (13) Å] is described by the torsion angles O3—S1—N1—C1, O2—S1—N1—C8 and N1—S1—C18—C19 (Table 1). The phenyl ring linked to the sulfonyl group is orthogonal to the indole moiety, forming a dihedral angle of 77.18 (4)°.

Compound (I) is the Z isomer and the C10—C16 bond is in a trans disposition with respect to the C2—C9 bond. The double bond has a nearly planar arrangement, since the r.m.s. deviation from the best plane passing through atoms N2/C10/C16/C9/C2 is 0.0195 (9) Å. Deviations from ideal geometry are observed in the bond angles around atoms C2, C9 and C10. While the C9—C10—C16 angle is close to the ideal value of 120°, the C1—C2—C9, C2—C9—C10 and N2—C10—C16 angles are more distorted, as a consequence of the strain induced by the double-bond linkage at C9—C10. The azabicyclic moiety presents very small distortions around atoms N2, C11, C12, C13, C14 and C15. The value of the C1—C2—C9—C10 torsion angle [25.1 (3)°] indicates a deviation of the indole ring from the plane of the double bond connected to the azabicyclic ring. However, the C2—C9 bond length [1.455 (2) Å], when compared with the standard value for a single bond connecting a Car atom to a Csp2 atom [1.470 (15) Å; Wilson, 1992], suggests extensive conjugation, beginning at atom N5 of the semicarbazone moiety and extending through to the indole ring in (I), which is also evident from the C10—C16 and C16—N3 bond lengths.

The mode of packing of (I), as viewed down the crystallographic b axis, is shown in Fig. 2. The molecules are linked by two types of hydrogen bonding. Atoms N4 and O1 are mutually hydrogen-bonded to an inversion-related molecule at (-x, -y, -z), leading to dimers, and atom N5 is hydrogen-bonded to sulfonyl atom O2 of a different inversion-related molecule at (-x + 1, -y, -z + 1). In addition to hydrogen bonding, ππ interactions between phenyl rings [3.433 (1) Å] of inversion-related molecules at (1 - x, 1 - y, 1 - z) and between different inversion-related indole rings at (1 - x, -y, 1 - z) (3.343 Å) link these dimers in an extended fashion parallel to the b axis.

Related literature top

For related literature, see: Allen (2002); Beddoes et al. (1986, 1994); Gomes et al. (1993); Govindasamy et al. (1998); Helliwell et al. (1997); Mason et al. (2003); Sekhar et al. (2007); Sonar et al. (2004); Wilson (1992); Zarza et al. (1988); Zhao et al. (1997, 1999).

Experimental top

The starting material, (II), was prepared according to the previously reported procedure of Sonar et al. (2004). The title compound, (I), was prepared by the reaction of (II) with semicarbazide to afford a single geometric isomer. Crystallization from methanol afforded yellow crystals. 1H NMR (DMSO-d6, δ, p.p.m.): 1.70 (m, 4H), 2.81 (m, 2H), 3.16 (m, 2H), 3.40 (s, 1H), 6.51 (b, 2H), 7.13 (s, 1H), 7.34 (m, 2H), 7.59 (t, 2H), 7.69 (t, 1H), 7.92 (d, 3H) 8.07 (d, 1H), 8.42 (s, 1H), 9.54 (s, 1H); 13C NMR (DMSO-d6, δ, p.p.m.): 24.63, 25.13, 46.62, 105.47, 112.94, 117.65, 120.31, 123.33, 124.94, 125.99, 126.38, 129.77, 130.18, 133.52, 134.54, 136.59, 146.02, 148.47, 157.27.

Refinement top

H atoms were found in difference Fourier maps and subsequently placed in idealized positions, with constrained distances of 0.95 (Csp2), 0.99 (CH2), 1.00 (CH) and 0.88 Å (NH). Uiso(H) values were set to 1.2Ueq of the attached atom.

Computing details top

Data collection: COLLECT (Nonius, 1999); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL (Sheldrick, 1995); software used to prepare material for publication: SHELXL97 and local programs.

Figures top
[Figure 1] Fig. 1. A view of the molecule of (I), with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii.
[Figure 2] Fig. 2. A packing diagram for (I), viewed down the b axis, showing the hydrogen-bonding interactions (dashed lines). For clarity, only those H atoms involved in hydrogen bonding are shown.
(Z)-2-[(1-Phenylsulfonyl-1H-indol-3-yl)methylene]-1-azabicyclo[2.2.2]octan-3-one semicarbazone top
Crystal data top
C23H23N5O3SF(000) = 944
Mr = 449.52Dx = 1.405 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5073 reflections
a = 11.2058 (2) Åθ = 1.0–27.5°
b = 12.7677 (2) ŵ = 0.19 mm1
c = 15.0499 (3) ÅT = 90 K
β = 99.3278 (9)°Block, yellow
V = 2124.75 (7) Å30.30 × 0.20 × 0.20 mm
Z = 4
Data collection top
Nonius KappaCCD area-detector
diffractometer
4851 independent reflections
Radiation source: fine-focus sealed tube3681 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
Detector resolution: 18 pixels mm-1θmax = 27.5°, θmin = 1.8°
ω scans at fixed χ = 55°h = 1414
Absorption correction: multi-scan
(SCALEPACK; Otwinowski & Minor, 1997)
k = 1616
Tmin = 0.945, Tmax = 0.963l = 1919
9258 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0574P)2 + 0.4741P]
where P = (Fo2 + 2Fc2)/3
4851 reflections(Δ/σ)max < 0.001
289 parametersΔρmax = 0.32 e Å3
0 restraintsΔρmin = 0.38 e Å3
Crystal data top
C23H23N5O3SV = 2124.75 (7) Å3
Mr = 449.52Z = 4
Monoclinic, P21/cMo Kα radiation
a = 11.2058 (2) ŵ = 0.19 mm1
b = 12.7677 (2) ÅT = 90 K
c = 15.0499 (3) Å0.30 × 0.20 × 0.20 mm
β = 99.3278 (9)°
Data collection top
Nonius KappaCCD area-detector
diffractometer
4851 independent reflections
Absorption correction: multi-scan
(SCALEPACK; Otwinowski & Minor, 1997)
3681 reflections with I > 2σ(I)
Tmin = 0.945, Tmax = 0.963Rint = 0.027
9258 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0400 restraints
wR(F2) = 0.111H-atom parameters constrained
S = 1.06Δρmax = 0.32 e Å3
4851 reflectionsΔρmin = 0.38 e Å3
289 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.52629 (4)0.23309 (3)0.65312 (3)0.02064 (12)
O10.06361 (10)0.12945 (9)0.01015 (7)0.0228 (3)
N10.51618 (11)0.17182 (10)0.55438 (8)0.0184 (3)
C10.40908 (14)0.16767 (12)0.49169 (10)0.0185 (3)
H10.33300.19430.50130.022*
O20.62682 (11)0.18602 (9)0.70982 (7)0.0277 (3)
N20.18784 (12)0.21890 (11)0.34876 (9)0.0214 (3)
C20.43040 (13)0.11985 (12)0.41515 (10)0.0163 (3)
O30.40802 (11)0.22977 (10)0.67635 (8)0.0274 (3)
N30.18362 (11)0.01288 (11)0.18193 (9)0.0198 (3)
C30.55802 (13)0.09339 (12)0.42848 (10)0.0164 (3)
N40.10182 (12)0.01862 (11)0.10775 (9)0.0212 (3)
H4A0.03620.01840.08930.025*
C40.62985 (14)0.04215 (13)0.37463 (11)0.0201 (3)
H40.59600.01750.31640.024*
N50.21256 (12)0.17097 (11)0.10530 (9)0.0228 (3)
H5A0.22870.23030.07990.027*
H5B0.25390.15290.15780.027*
C50.75117 (15)0.02789 (13)0.40746 (11)0.0236 (4)
H50.80070.00820.37190.028*
C60.80220 (14)0.06584 (13)0.49234 (11)0.0237 (4)
H60.88650.05710.51230.028*
C70.73292 (14)0.11590 (12)0.54810 (11)0.0215 (3)
H70.76740.14060.60620.026*
C80.61085 (14)0.12816 (12)0.51490 (10)0.0175 (3)
C90.34470 (13)0.08920 (12)0.33617 (10)0.0170 (3)
H90.36910.03330.30160.020*
C100.23579 (14)0.13025 (12)0.30645 (10)0.0178 (3)
C110.15035 (16)0.30028 (13)0.27930 (12)0.0268 (4)
H11A0.22140.32170.25220.032*
H11B0.12100.36270.30830.032*
C120.04970 (17)0.26100 (14)0.20419 (12)0.0311 (4)
H12A0.02620.29990.20630.037*
H12B0.07370.27240.14440.037*
C130.03073 (14)0.14414 (14)0.21932 (11)0.0246 (4)
H130.02830.11340.16910.030*
C140.01258 (16)0.12963 (16)0.31082 (12)0.0322 (4)
H14A0.01820.05410.32440.039*
H14B0.09360.16130.30870.039*
C150.07947 (15)0.18361 (15)0.38475 (12)0.0289 (4)
H15A0.04060.24460.40890.035*
H15B0.10400.13390.43490.035*
C160.15120 (13)0.08962 (12)0.22868 (10)0.0177 (3)
C170.12469 (14)0.10794 (13)0.06382 (10)0.0194 (3)
C180.56295 (14)0.36276 (13)0.63079 (10)0.0186 (3)
C190.47539 (14)0.44052 (13)0.63028 (10)0.0218 (4)
H190.39610.42340.64020.026*
C200.50653 (15)0.54334 (14)0.61499 (11)0.0249 (4)
H200.44850.59750.61540.030*
C210.62182 (15)0.56746 (14)0.59919 (11)0.0256 (4)
H210.64270.63820.58930.031*
C220.70691 (15)0.48886 (13)0.59772 (12)0.0270 (4)
H220.78500.50570.58510.032*
C230.67862 (14)0.38589 (13)0.61449 (11)0.0227 (4)
H230.73720.33210.61480.027*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0274 (2)0.0202 (2)0.01356 (19)0.00139 (16)0.00103 (15)0.00125 (16)
O10.0246 (6)0.0214 (6)0.0199 (6)0.0007 (5)0.0034 (5)0.0035 (5)
N10.0196 (7)0.0188 (7)0.0159 (6)0.0007 (5)0.0002 (5)0.0019 (6)
C10.0171 (8)0.0180 (8)0.0196 (8)0.0006 (6)0.0008 (6)0.0015 (6)
O20.0381 (7)0.0237 (7)0.0179 (6)0.0035 (5)0.0061 (5)0.0012 (5)
N20.0232 (7)0.0211 (8)0.0188 (7)0.0047 (6)0.0002 (5)0.0019 (6)
C20.0171 (8)0.0149 (8)0.0167 (7)0.0000 (6)0.0021 (6)0.0026 (6)
O30.0324 (7)0.0294 (7)0.0222 (6)0.0059 (5)0.0103 (5)0.0041 (5)
N30.0187 (7)0.0216 (7)0.0175 (6)0.0025 (5)0.0021 (5)0.0022 (6)
C30.0183 (8)0.0137 (8)0.0168 (7)0.0007 (6)0.0015 (6)0.0035 (6)
N40.0174 (7)0.0231 (8)0.0207 (7)0.0018 (5)0.0045 (5)0.0046 (6)
C40.0240 (8)0.0193 (9)0.0176 (7)0.0015 (6)0.0050 (6)0.0010 (6)
N50.0259 (7)0.0213 (7)0.0190 (7)0.0019 (6)0.0029 (6)0.0038 (6)
C50.0230 (8)0.0212 (9)0.0278 (9)0.0022 (7)0.0076 (7)0.0016 (7)
C60.0167 (8)0.0207 (9)0.0330 (9)0.0021 (6)0.0014 (7)0.0049 (7)
C70.0218 (8)0.0176 (8)0.0229 (8)0.0034 (6)0.0028 (6)0.0025 (7)
C80.0200 (8)0.0143 (8)0.0181 (7)0.0007 (6)0.0031 (6)0.0024 (6)
C90.0209 (8)0.0160 (8)0.0142 (7)0.0014 (6)0.0030 (6)0.0007 (6)
C100.0206 (8)0.0183 (8)0.0145 (7)0.0001 (6)0.0028 (6)0.0001 (6)
C110.0291 (9)0.0200 (9)0.0293 (9)0.0034 (7)0.0013 (7)0.0010 (7)
C120.0340 (10)0.0274 (10)0.0276 (9)0.0102 (8)0.0078 (8)0.0016 (8)
C130.0181 (8)0.0279 (9)0.0261 (8)0.0022 (7)0.0015 (6)0.0077 (7)
C140.0240 (9)0.0380 (12)0.0370 (10)0.0009 (8)0.0123 (8)0.0104 (9)
C150.0290 (9)0.0342 (11)0.0247 (9)0.0058 (8)0.0077 (7)0.0032 (8)
C160.0177 (8)0.0176 (8)0.0177 (7)0.0012 (6)0.0030 (6)0.0009 (6)
C170.0191 (8)0.0198 (8)0.0191 (8)0.0034 (6)0.0024 (6)0.0004 (7)
C180.0228 (8)0.0180 (8)0.0138 (7)0.0002 (6)0.0010 (6)0.0016 (6)
C190.0202 (8)0.0280 (9)0.0167 (7)0.0010 (7)0.0010 (6)0.0040 (7)
C200.0289 (9)0.0232 (9)0.0205 (8)0.0080 (7)0.0029 (7)0.0042 (7)
C210.0327 (10)0.0186 (9)0.0238 (8)0.0001 (7)0.0005 (7)0.0017 (7)
C220.0247 (9)0.0243 (9)0.0313 (9)0.0042 (7)0.0020 (7)0.0037 (8)
C230.0215 (8)0.0191 (9)0.0259 (8)0.0018 (6)0.0010 (7)0.0052 (7)
Geometric parameters (Å, º) top
S1—O31.4250 (12)C7—H70.9500
S1—O21.4307 (12)C9—C101.337 (2)
S1—N11.6668 (13)C9—H90.9500
S1—C181.7514 (17)C10—C161.476 (2)
O1—C171.2394 (18)C11—C121.545 (2)
N1—C11.4023 (19)C11—H11A0.9900
N1—C81.4120 (19)C11—H11B0.9900
C1—C21.359 (2)C12—C131.529 (3)
C1—H10.9500C12—H12A0.9900
N2—C101.444 (2)C12—H12B0.9900
N2—C151.478 (2)C13—C161.505 (2)
N2—C111.485 (2)C13—C141.544 (2)
C2—C31.451 (2)C13—H131.0000
C2—C91.455 (2)C14—C151.551 (2)
N3—C161.292 (2)C14—H14A0.9900
N3—N41.3844 (17)C14—H14B0.9900
C3—C41.394 (2)C15—H15A0.9900
C3—C81.411 (2)C15—H15B0.9900
N4—C171.363 (2)C18—C231.389 (2)
N4—H4A0.8800C18—C191.395 (2)
C4—C51.381 (2)C19—C201.387 (2)
C4—H40.9500C19—H190.9500
N5—C171.344 (2)C20—C211.386 (2)
N5—H5A0.8800C20—H200.9500
N5—H5B0.8800C21—C221.387 (2)
C5—C61.399 (2)C21—H210.9500
C5—H50.9500C22—C231.385 (2)
C6—C71.388 (2)C22—H220.9500
C6—H60.9500C23—H230.9500
C7—C81.387 (2)
O3—S1—O2120.99 (7)N2—C11—H11B109.2
O3—S1—N1105.86 (7)C12—C11—H11B109.2
O2—S1—N1105.53 (7)H11A—C11—H11B107.9
O3—S1—C18109.37 (8)C13—C12—C11108.08 (14)
O2—S1—C18108.96 (7)C13—C12—H12A110.1
N1—S1—C18104.88 (7)C11—C12—H12A110.1
C1—N1—C8108.74 (12)C13—C12—H12B110.1
C1—N1—S1123.01 (11)C11—C12—H12B110.1
C8—N1—S1127.83 (10)H12A—C12—H12B108.4
C2—C1—N1109.79 (13)C16—C13—C12108.72 (14)
C2—C1—H1125.1C16—C13—C14105.54 (14)
N1—C1—H1125.1C12—C13—C14108.74 (15)
C10—N2—C15108.00 (13)C16—C13—H13111.2
C10—N2—C11108.71 (12)C12—C13—H13111.2
C15—N2—C11108.41 (13)C14—C13—H13111.2
C1—C2—C3106.99 (13)C13—C14—C15108.54 (14)
C1—C2—C9129.03 (14)C13—C14—H14A110.0
C3—C2—C9123.73 (13)C15—C14—H14A110.0
C16—N3—N4116.84 (13)C13—C14—H14B110.0
C4—C3—C8119.21 (14)C15—C14—H14B110.0
C4—C3—C2132.66 (14)H14A—C14—H14B108.4
C8—C3—C2108.12 (13)N2—C15—C14111.29 (13)
C17—N4—N3118.83 (13)N2—C15—H15A109.4
C17—N4—H4A120.6C14—C15—H15A109.4
N3—N4—H4A120.6N2—C15—H15B109.4
C5—C4—C3118.77 (15)C14—C15—H15B109.4
C5—C4—H4120.6H15A—C15—H15B108.0
C3—C4—H4120.6N3—C16—C10119.82 (14)
C17—N5—H5A120.0N3—C16—C13128.82 (14)
C17—N5—H5B120.0C10—C16—C13111.26 (13)
H5A—N5—H5B120.0O1—C17—N5122.73 (15)
C4—C5—C6120.93 (15)O1—C17—N4120.07 (14)
C4—C5—H5119.5N5—C17—N4117.18 (13)
C6—C5—H5119.5C23—C18—C19121.55 (15)
C7—C6—C5121.71 (15)C23—C18—S1119.29 (12)
C7—C6—H6119.1C19—C18—S1119.15 (12)
C5—C6—H6119.1C20—C19—C18118.61 (15)
C8—C7—C6116.73 (15)C20—C19—H19120.7
C8—C7—H7121.6C18—C19—H19120.7
C6—C7—H7121.6C21—C20—C19120.36 (15)
C7—C8—C3122.60 (14)C21—C20—H20119.8
C7—C8—N1131.09 (14)C19—C20—H20119.8
C3—C8—N1106.30 (13)C20—C21—C22120.29 (17)
C10—C9—C2127.85 (14)C20—C21—H21119.9
C10—C9—H9116.1C22—C21—H21119.9
C2—C9—H9116.1C23—C22—C21120.37 (16)
C9—C10—N2122.99 (14)C23—C22—H22119.8
C9—C10—C16124.17 (14)C21—C22—H22119.8
N2—C10—C16112.84 (13)C22—C23—C18118.78 (15)
N2—C11—C12112.17 (14)C22—C23—H23120.6
N2—C11—H11A109.2C18—C23—H23120.6
C12—C11—H11A109.2
O3—S1—N1—C127.83 (14)C11—N2—C10—C1654.35 (17)
O2—S1—N1—C1157.21 (12)C10—N2—C11—C1261.52 (18)
C18—S1—N1—C187.77 (13)C15—N2—C11—C1255.65 (18)
O3—S1—N1—C8160.46 (13)N2—C11—C12—C136.9 (2)
O2—S1—N1—C831.08 (15)C11—C12—C13—C1651.93 (18)
C18—S1—N1—C883.93 (14)C11—C12—C13—C1462.51 (18)
C8—N1—C1—C22.20 (17)C16—C13—C14—C1561.99 (18)
S1—N1—C1—C2175.29 (11)C12—C13—C14—C1554.51 (19)
N1—C1—C2—C31.00 (17)C10—N2—C15—C1453.66 (18)
N1—C1—C2—C9173.35 (15)C11—N2—C15—C1463.96 (18)
C1—C2—C3—C4178.39 (17)C13—C14—C15—N28.0 (2)
C9—C2—C3—C43.7 (3)N4—N3—C16—C10177.48 (13)
C1—C2—C3—C80.55 (17)N4—N3—C16—C136.5 (2)
C9—C2—C3—C8175.28 (14)C9—C10—C16—N33.7 (2)
C16—N3—N4—C17171.07 (14)N2—C10—C16—N3177.31 (14)
C8—C3—C4—C50.6 (2)C9—C10—C16—C13172.99 (15)
C2—C3—C4—C5179.45 (16)N2—C10—C16—C136.05 (18)
C3—C4—C5—C61.3 (2)C12—C13—C16—N3122.76 (18)
C4—C5—C6—C72.2 (2)C14—C13—C16—N3120.73 (18)
C5—C6—C7—C81.1 (2)C12—C13—C16—C1060.98 (17)
C6—C7—C8—C30.8 (2)C14—C13—C16—C1055.53 (17)
C6—C7—C8—N1177.86 (15)N3—N4—C17—O1168.96 (14)
C4—C3—C8—C71.7 (2)N3—N4—C17—N512.8 (2)
C2—C3—C8—C7179.17 (14)O3—S1—C18—C23174.30 (12)
C4—C3—C8—N1177.26 (14)O2—S1—C18—C2340.05 (14)
C2—C3—C8—N11.85 (16)N1—S1—C18—C2372.55 (13)
C1—N1—C8—C7178.68 (16)O3—S1—C18—C195.35 (15)
S1—N1—C8—C76.0 (2)O2—S1—C18—C19139.61 (12)
C1—N1—C8—C32.46 (16)N1—S1—C18—C19107.79 (13)
S1—N1—C8—C3175.13 (11)C23—C18—C19—C201.4 (2)
C1—C2—C9—C1025.1 (3)S1—C18—C19—C20178.23 (12)
C3—C2—C9—C10161.39 (15)C18—C19—C20—C211.0 (2)
C2—C9—C10—N23.1 (3)C19—C20—C21—C220.6 (2)
C2—C9—C10—C16175.84 (14)C20—C21—C22—C231.8 (3)
C15—N2—C10—C9115.97 (17)C21—C22—C23—C181.4 (2)
C11—N2—C10—C9126.60 (16)C19—C18—C23—C220.2 (2)
C15—N2—C10—C1663.08 (16)S1—C18—C23—C22179.42 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4A···O1i0.882.062.8785 (17)154
N5—H5B···O2ii0.882.253.0651 (17)154
Symmetry codes: (i) x, y, z; (ii) x+1, y, z+1.

Experimental details

Crystal data
Chemical formulaC23H23N5O3S
Mr449.52
Crystal system, space groupMonoclinic, P21/c
Temperature (K)90
a, b, c (Å)11.2058 (2), 12.7677 (2), 15.0499 (3)
β (°) 99.3278 (9)
V3)2124.75 (7)
Z4
Radiation typeMo Kα
µ (mm1)0.19
Crystal size (mm)0.30 × 0.20 × 0.20
Data collection
DiffractometerNonius KappaCCD area-detector
diffractometer
Absorption correctionMulti-scan
(SCALEPACK; Otwinowski & Minor, 1997)
Tmin, Tmax0.945, 0.963
No. of measured, independent and
observed [I > 2σ(I)] reflections
9258, 4851, 3681
Rint0.027
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.040, 0.111, 1.06
No. of reflections4851
No. of parameters289
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.32, 0.38

Computer programs: COLLECT (Nonius, 1999), SCALEPACK (Otwinowski & Minor, 1997), DENZO-SMN (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), XP in SHELXTL (Sheldrick, 1995), SHELXL97 and local programs.

Selected geometric parameters (Å, º) top
S1—O21.4307 (12)N3—C161.292 (2)
S1—N11.6668 (13)N3—N41.3844 (17)
S1—C181.7514 (17)N5—C171.344 (2)
O1—C171.2394 (18)C9—C101.337 (2)
C2—C91.455 (2)C10—C161.476 (2)
C1—C2—C9129.03 (14)C9—C10—N2122.99 (14)
C10—C9—C2127.85 (14)N2—C10—C16112.84 (13)
O3—S1—N1—C127.83 (14)C9—C10—C16—N33.7 (2)
O2—S1—N1—C831.08 (15)N1—S1—C18—C19107.79 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4A···O1i0.882.062.8785 (17)154.0
N5—H5B···O2ii0.882.253.0651 (17)153.7
Symmetry codes: (i) x, y, z; (ii) x+1, y, z+1.
 

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