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Acta Crystallogr Sect E Struct Rep Online. 2008 September 1; 64(Pt 9): o1836.
Published online 2008 August 30. doi:  10.1107/S1600536808019995
PMCID: PMC2960670

2,9-Bis(1,3-benzothia­zol-2-yl)-1,10-phenanthroline dichloro­methane disolvate

Abstract

In the title compound, C26H14N4S2·2CH2Cl2, the two pendant benzothia­zole groups are slightly twisted with respect to the phenanthroline core [dihedral angles = 1.03 (7) and 9.05 (5)°]. Weak inter­molecular C—H(...)N and C—H(...)Cl inter­actions occur in the crystal structure.

Related literature

For related literature, see: Kerbs (2003 [triangle]); Gude et al. (2005 [triangle]).

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Object name is e-64-o1836-scheme1.jpg

Experimental

Crystal data

  • C26H14N4S2·2CH2Cl2
  • M r = 616.38
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1836-efi1.jpg
  • a = 8.0969 (2) Å
  • b = 12.3990 (2) Å
  • c = 14.6006 (3) Å
  • α = 108.234 (1)°
  • β = 102.181 (1)°
  • γ = 94.335 (1)°
  • V = 1344.93 (5) Å3
  • Z = 2
  • Cu Kα radiation
  • μ = 5.67 mm−1
  • T = 100 (2) K
  • 0.75 × 0.07 × 0.05 mm

Data collection

  • Bruker APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.101, T max = 0.765
  • 10764 measured reflections
  • 4352 independent reflections
  • 3831 reflections with I > 2σ(I)
  • R int = 0.021

Refinement

  • R[F 2 > 2σ(F 2)] = 0.031
  • wR(F 2) = 0.079
  • S = 1.00
  • 4352 reflections
  • 415 parameters
  • All H-atom parameters refined
  • Δρmax = 0.37 e Å−3
  • Δρmin = −0.38 e Å−3

Data collection: APEX2 (Bruker, 2005 [triangle]); cell refinement: SAINT (Bruker, 2005 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: XP (Bruker, 2005 [triangle]); software used to prepare material for publication: XCIF (Bruker, 2005 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808019995/hb2737sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808019995/hb2737Isup2.hkl

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

supplementary crystallographic information

Comment

As part of our studies of the biological properties of Schiff bases, we attempted to synthesize Schiff bases from 1,10-phenanthroline. It has been found in the literature that Schiff bases formed from S-alkyl and S-aryl substituted amines contain both hard nitrogen and soft sulfur donor atoms. (e.g. Kerbs, 2003). Consequently, these compounds are capable of forming stable complexes with a wide variety of metal ions. These complexes have interesting physio-chemical properties and potential chemotherapeutic effets (e.g. Gude et al.2005). In this paper the synthesis and structure of the title compound, (I), are reported.

The main molecule is close to planar, with dihedral angles of 9.05 (5)° and 1.03 (7)° for the S1 and S2 benzothiazolyl moieties respectively, with respect to the phenanthroline core. There are two dichloromethane solvent molecules in the asymmetric unit (Fig. 1).

Weak intermolecular C—H···N and C—H···Cl interactions (Table 1) may help to stabilise the packing.

Experimental

To a solution of 1,10-phenanthroline (50 mg, 0.20 mmol) in 5 ml CHCl3, 2-mercaptoaniline (0.60 µL, 0.40 mmol) was added followed by the addition of p-toluene sulfonic acid mono hydrate (76 mg, 0.40 mmol) in a Pyrex tube under argon. The tube was placed in a CEM microwave. The reaction conditions were set up as follows: power: 300 W, ramp time: 20 min, hold time: 20 min, and temperature: 373 K. When the reaction vessel was opened, a yellow precipitate was observed, which was filtered off and washed with cold CHCl3 and dried under vacuum. [y: 30 mg, 40%]. IR: ν= 1597 cm-1 (C=N), 1550 cm-1 (C=C). 1H-NMR([D3],CDCl3, 300 MHz): δ=8.74 (d, 4J= 9.0 Hz,, 8-H, 3-H), 8.41 (d, 3J=9.0 Hz,2H, H-4, H-7), 7.88 (s, 2H, H-5, and H-6), 8.169 (t, 4H, 2 J= 8.1 Hz, 1J=8.7 Hz,H-16, H-16', H-13, H-13'), 7.53 (m, 4H, H-14, H-14', H-15, H-15').13 C: NMR([D3], CDCl3, 75.5 MHz): δ= 155 (C-2, C-9), δ= 146 (C-11,C-12), δ=137.48 (C-3, C-8). δ=127.591 (C-4, C-7,), δ=126.60 (C-5, C-6), δ= 172 (C-13, C-13'), δ= 152 (C-14, C-14'), δ= 130.26 (C-15, C-15'), δ=137.0 (C-19, C-19') δ=126.18 (C-19, C-19'). δ=124.04 (C-18, C-18'). δ=122.54 (C-17, C-17'). δ=120.51 (C-16, C-16').

Yellow needles of (I) were grown from CH2Cl2/hexane at 253 K.

Refinement

The H atoms were located in difference maps and their positions and Uiso values were freely refined.

Figures

Fig. 1.
The molecular structure of (I) showing 50% displacement ellipsoids for the non-hydrogen atoms.
Fig. 2.
The formation of the title compound.

Crystal data

C26H14N4S2·2CH2Cl2Z = 2
Mr = 616.38F000 = 628
Triclinic, P1Dx = 1.522 Mg m3
Hall symbol: -P 1Melting point > 573 K
a = 8.0969 (2) ÅCu Kα radiation λ = 1.54178 Å
b = 12.3990 (2) ÅCell parameters from 5710 reflections
c = 14.6006 (3) Åθ = 3–65º
α = 108.234 (1)ºµ = 5.67 mm1
β = 102.181 (1)ºT = 100 (2) K
γ = 94.335 (1)ºNeedle, yellow
V = 1344.93 (5) Å30.75 × 0.07 × 0.05 mm

Data collection

Bruker APEXII CCD diffractometer4352 independent reflections
Radiation source: fine-focus sealed tube3831 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.021
T = 100(2) Kθmax = 66.5º
ω scansθmin = 3.3º
Absorption correction: multi-scan(SADABS; Bruker, 2005)h = −9→9
Tmin = 0.101, Tmax = 0.765k = −14→13
10764 measured reflectionsl = 0→17

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.031All H-atom parameters refined
wR(F2) = 0.079  w = 1/[σ2(Fo2) + (0.0482P)2 + 0.6095P] where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.001
4352 reflectionsΔρmax = 0.37 e Å3
415 parametersΔρmin = −0.38 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

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.

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

xyzUiso*/Ueq
S1−0.16197 (6)0.64055 (4)0.22928 (3)0.02003 (12)
S20.22351 (6)0.40021 (4)0.33879 (3)0.01732 (12)
N1−0.02010 (19)0.73385 (13)0.44545 (11)0.0161 (3)
N20.17914 (18)0.58715 (12)0.50867 (11)0.0155 (3)
N3−0.2641 (2)0.84086 (13)0.26682 (12)0.0211 (4)
N40.39069 (19)0.33830 (12)0.48236 (11)0.0167 (3)
C1−0.1189 (2)0.80420 (15)0.41677 (14)0.0172 (4)
C2−0.1611 (2)0.90203 (16)0.48337 (14)0.0195 (4)
C3−0.0951 (2)0.92663 (16)0.58255 (14)0.0195 (4)
C40.0093 (2)0.85441 (15)0.61687 (13)0.0164 (4)
C50.0753 (2)0.87447 (16)0.72043 (14)0.0186 (4)
C60.1658 (2)0.79970 (16)0.75169 (14)0.0196 (4)
C70.2011 (2)0.69974 (15)0.68113 (13)0.0167 (4)
C80.2901 (2)0.61883 (16)0.71135 (14)0.0188 (4)
C90.3234 (2)0.52576 (16)0.64199 (14)0.0180 (4)
C100.2672 (2)0.51431 (15)0.54114 (14)0.0160 (4)
C110.0425 (2)0.75722 (15)0.54414 (13)0.0156 (4)
C120.1452 (2)0.67863 (15)0.57772 (13)0.0159 (4)
C13−0.1855 (2)0.77490 (15)0.30927 (14)0.0174 (4)
C14−0.2697 (2)0.67676 (16)0.12950 (14)0.0198 (4)
C15−0.3127 (2)0.78754 (16)0.16477 (14)0.0202 (4)
C16−0.3991 (3)0.83493 (19)0.09613 (15)0.0274 (5)
C17−0.4411 (3)0.77107 (19)−0.00363 (16)0.0295 (5)
C18−0.3985 (3)0.66055 (19)−0.03754 (16)0.0280 (5)
C19−0.3121 (3)0.61241 (18)0.02860 (15)0.0247 (4)
C200.3034 (2)0.41652 (15)0.46417 (13)0.0154 (4)
C210.3131 (2)0.27520 (15)0.30739 (14)0.0177 (4)
C220.3991 (2)0.25688 (15)0.39417 (14)0.0171 (4)
C230.4800 (2)0.15927 (16)0.38635 (15)0.0196 (4)
C240.4739 (2)0.08355 (16)0.29330 (15)0.0221 (4)
C250.3865 (3)0.10262 (17)0.20755 (15)0.0245 (4)
C260.3058 (2)0.19776 (17)0.21311 (15)0.0219 (4)
H2−0.233 (3)0.9445 (19)0.4549 (16)0.028 (6)*
H3−0.118 (2)0.9906 (18)0.6279 (15)0.017 (5)*
H50.054 (2)0.9395 (18)0.7645 (15)0.016 (5)*
H60.207 (2)0.8083 (16)0.8204 (15)0.015 (5)*
H80.328 (2)0.6297 (17)0.7835 (16)0.021 (5)*
H90.380 (3)0.4734 (18)0.6609 (15)0.022 (5)*
H16−0.425 (3)0.909 (2)0.1181 (16)0.029 (6)*
H17−0.504 (3)0.803 (2)−0.0520 (17)0.034 (6)*
H18−0.429 (2)0.6211 (17)−0.1043 (16)0.019 (5)*
H19−0.286 (3)0.535 (2)0.0041 (16)0.029 (6)*
H230.535 (3)0.1458 (18)0.4413 (16)0.021 (5)*
H240.528 (3)0.0190 (19)0.2872 (15)0.023 (5)*
H250.381 (3)0.0496 (19)0.1426 (16)0.025 (6)*
H260.245 (3)0.2090 (17)0.1567 (16)0.021 (5)*
Cl1S0.32173 (7)0.83312 (4)0.34294 (4)0.03355 (14)
Cl2S0.32540 (7)0.60371 (4)0.20953 (4)0.03418 (14)
C1S0.3093 (3)0.68551 (17)0.33012 (15)0.0217 (4)
H1SA0.201 (3)0.6616 (17)0.3398 (14)0.020 (5)*
H1SB0.403 (3)0.6741 (18)0.3742 (16)0.026 (6)*
Cl3S0.07322 (8)0.63525 (5)0.93119 (5)0.04547 (17)
Cl4S0.05564 (10)0.87470 (6)1.03272 (6)0.0674 (2)
C2S0.1165 (3)0.7470 (2)1.04721 (19)0.0406 (6)
H2SA0.241 (4)0.763 (2)1.0784 (19)0.049 (7)*
H2SB0.047 (3)0.726 (2)1.087 (2)0.049 (8)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0242 (3)0.0178 (2)0.0193 (2)0.00770 (18)0.00485 (18)0.00731 (19)
S20.0174 (2)0.0169 (2)0.0178 (2)0.00438 (17)0.00378 (17)0.00611 (18)
N10.0145 (8)0.0172 (8)0.0189 (8)0.0021 (6)0.0067 (6)0.0076 (6)
N20.0128 (8)0.0152 (8)0.0189 (8)0.0011 (6)0.0053 (6)0.0058 (6)
N30.0232 (9)0.0223 (9)0.0222 (9)0.0082 (7)0.0080 (7)0.0109 (7)
N40.0146 (8)0.0159 (8)0.0204 (8)0.0020 (6)0.0054 (6)0.0066 (6)
C10.0142 (9)0.0175 (9)0.0226 (10)0.0019 (7)0.0076 (7)0.0085 (8)
C20.0198 (10)0.0174 (9)0.0251 (10)0.0062 (8)0.0087 (8)0.0097 (8)
C30.0205 (10)0.0154 (10)0.0241 (10)0.0028 (8)0.0100 (8)0.0057 (8)
C40.0136 (9)0.0153 (9)0.0210 (10)0.0000 (7)0.0073 (7)0.0055 (7)
C50.0174 (10)0.0163 (10)0.0206 (10)0.0009 (7)0.0079 (7)0.0025 (8)
C60.0180 (10)0.0232 (10)0.0168 (10)0.0010 (8)0.0053 (7)0.0054 (8)
C70.0124 (9)0.0185 (9)0.0185 (9)−0.0010 (7)0.0041 (7)0.0059 (8)
C80.0144 (9)0.0225 (10)0.0203 (10)0.0009 (7)0.0045 (7)0.0086 (8)
C90.0149 (10)0.0186 (10)0.0224 (10)0.0038 (8)0.0040 (7)0.0098 (8)
C100.0104 (9)0.0148 (9)0.0233 (10)0.0002 (7)0.0054 (7)0.0069 (8)
C110.0121 (9)0.0162 (9)0.0201 (10)−0.0005 (7)0.0060 (7)0.0076 (7)
C120.0119 (9)0.0155 (9)0.0209 (10)−0.0006 (7)0.0063 (7)0.0062 (8)
C130.0161 (10)0.0169 (9)0.0222 (10)0.0032 (7)0.0093 (7)0.0078 (8)
C140.0163 (10)0.0237 (10)0.0228 (10)0.0051 (8)0.0065 (7)0.0110 (8)
C150.0203 (10)0.0228 (10)0.0206 (10)0.0065 (8)0.0077 (7)0.0089 (8)
C160.0330 (12)0.0290 (12)0.0264 (11)0.0177 (9)0.0105 (9)0.0128 (9)
C170.0310 (12)0.0381 (13)0.0238 (11)0.0151 (10)0.0061 (9)0.0145 (10)
C180.0301 (12)0.0337 (12)0.0187 (11)0.0105 (9)0.0040 (8)0.0069 (9)
C190.0260 (11)0.0233 (11)0.0239 (11)0.0069 (8)0.0048 (8)0.0068 (9)
C200.0109 (9)0.0163 (9)0.0199 (9)−0.0003 (7)0.0042 (7)0.0077 (7)
C210.0136 (9)0.0165 (9)0.0235 (10)0.0017 (7)0.0053 (7)0.0072 (8)
C220.0141 (9)0.0163 (9)0.0209 (10)−0.0011 (7)0.0057 (7)0.0062 (8)
C230.0174 (10)0.0185 (10)0.0271 (11)0.0030 (7)0.0080 (8)0.0116 (8)
C240.0206 (10)0.0155 (10)0.0323 (12)0.0028 (8)0.0115 (8)0.0077 (8)
C250.0237 (11)0.0199 (10)0.0254 (11)0.0005 (8)0.0086 (8)0.0005 (9)
C260.0182 (10)0.0241 (10)0.0201 (10)0.0017 (8)0.0027 (8)0.0045 (8)
Cl1S0.0412 (3)0.0209 (3)0.0436 (3)0.0111 (2)0.0151 (2)0.0133 (2)
Cl2S0.0537 (4)0.0306 (3)0.0227 (3)0.0168 (2)0.0146 (2)0.0094 (2)
C1S0.0249 (11)0.0205 (10)0.0228 (11)0.0081 (8)0.0076 (8)0.0095 (8)
Cl3S0.0506 (4)0.0385 (3)0.0509 (4)0.0138 (3)0.0195 (3)0.0139 (3)
Cl4S0.0650 (5)0.0360 (4)0.0686 (5)0.0069 (3)−0.0205 (4)−0.0029 (3)
C2S0.0348 (14)0.0513 (15)0.0376 (14)0.0033 (11)0.0082 (11)0.0187 (12)

Geometric parameters (Å, °)

S1—C141.7370 (19)C10—C201.469 (2)
S1—C131.7607 (18)C11—C121.460 (2)
S2—C211.7334 (18)C14—C191.391 (3)
S2—C201.7491 (18)C14—C151.407 (3)
N1—C11.330 (2)C15—C161.405 (3)
N1—C111.351 (2)C16—C171.376 (3)
N2—C101.331 (2)C16—H160.94 (2)
N2—C121.352 (2)C17—C181.400 (3)
N3—C131.299 (2)C17—H170.98 (2)
N3—C151.382 (2)C18—C191.385 (3)
N4—C201.303 (2)C18—H180.91 (2)
N4—C221.384 (2)C19—H190.97 (2)
C1—C21.414 (3)C21—C261.397 (3)
C1—C131.464 (3)C21—C221.405 (3)
C2—C31.359 (3)C22—C231.404 (3)
C2—H20.93 (2)C23—C241.377 (3)
C3—C41.408 (3)C23—H230.90 (2)
C3—H30.92 (2)C24—C251.400 (3)
C4—C111.422 (3)C24—H240.93 (2)
C4—C51.427 (3)C25—C261.380 (3)
C5—C61.353 (3)C25—H250.96 (2)
C5—H50.92 (2)C26—H260.92 (2)
C6—C71.435 (3)Cl1S—C1S1.7733 (19)
C6—H60.96 (2)Cl2S—C1S1.773 (2)
C7—C81.405 (3)C1S—H1SA0.95 (2)
C7—C121.414 (3)C1S—H1SB0.94 (2)
C8—C91.364 (3)Cl3S—C2S1.766 (3)
C8—H80.99 (2)Cl4S—C2S1.754 (3)
C9—C101.404 (3)C2S—H2SA0.99 (3)
C9—H90.90 (2)C2S—H2SB0.97 (3)
C14—S1—C1388.49 (9)N3—C15—C16125.46 (18)
C21—S2—C2088.48 (9)N3—C15—C14115.44 (17)
C1—N1—C11117.85 (15)C16—C15—C14119.10 (18)
C10—N2—C12117.47 (15)C17—C16—C15119.06 (19)
C13—N3—C15110.46 (16)C17—C16—H16120.7 (14)
C20—N4—C22110.30 (15)C15—C16—H16120.3 (14)
N1—C1—C2123.86 (17)C16—C17—C18121.17 (19)
N1—C1—C13116.02 (16)C16—C17—H17119.5 (13)
C2—C1—C13120.12 (16)C18—C17—H17119.3 (13)
C3—C2—C1118.15 (18)C19—C18—C17120.83 (19)
C3—C2—H2125.4 (14)C19—C18—H18120.8 (13)
C1—C2—H2116.4 (14)C17—C18—H18118.4 (13)
C2—C3—C4120.23 (18)C18—C19—C14118.09 (19)
C2—C3—H3120.3 (12)C18—C19—H19119.8 (13)
C4—C3—H3119.5 (12)C14—C19—H19122.1 (13)
C3—C4—C11117.41 (17)N4—C20—C10124.42 (16)
C3—C4—C5122.00 (17)N4—C20—S2116.40 (14)
C11—C4—C5120.56 (17)C10—C20—S2119.17 (13)
C6—C5—C4120.92 (17)C26—C21—C22121.22 (17)
C6—C5—H5121.6 (12)C26—C21—S2128.96 (15)
C4—C5—H5117.4 (12)C22—C21—S2109.82 (14)
C5—C6—C7120.55 (17)N4—C22—C23125.39 (17)
C5—C6—H6123.3 (12)N4—C22—C21114.98 (16)
C7—C6—H6116.1 (12)C23—C22—C21119.60 (17)
C8—C7—C12117.46 (16)C24—C23—C22119.06 (19)
C8—C7—C6121.80 (17)C24—C23—H23120.1 (13)
C12—C7—C6120.73 (16)C22—C23—H23120.9 (13)
C9—C8—C7120.03 (17)C23—C24—C25120.61 (18)
C9—C8—H8120.5 (12)C23—C24—H24119.8 (13)
C7—C8—H8119.5 (12)C25—C24—H24119.6 (13)
C8—C9—C10118.20 (17)C26—C25—C24121.51 (19)
C8—C9—H9120.5 (13)C26—C25—H25117.7 (13)
C10—C9—H9121.3 (13)C24—C25—H25120.8 (13)
N2—C10—C9124.03 (17)C25—C26—C21117.99 (19)
N2—C10—C20116.04 (16)C25—C26—H26121.5 (13)
C9—C10—C20119.93 (16)C21—C26—H26120.4 (13)
N1—C11—C4122.47 (16)Cl2S—C1S—Cl1S110.15 (11)
N1—C11—C12118.95 (16)Cl2S—C1S—H1SA109.8 (12)
C4—C11—C12118.57 (16)Cl1S—C1S—H1SA107.6 (12)
N2—C12—C7122.76 (16)Cl2S—C1S—H1SB105.3 (13)
N2—C12—C11118.65 (16)Cl1S—C1S—H1SB110.1 (13)
C7—C12—C11118.56 (16)H1SA—C1S—H1SB113.8 (18)
N3—C13—C1124.79 (16)Cl4S—C2S—Cl3S111.12 (14)
N3—C13—S1116.14 (14)Cl4S—C2S—H2SA106.9 (15)
C1—C13—S1119.06 (13)Cl3S—C2S—H2SA109.9 (15)
C19—C14—C15121.75 (18)Cl4S—C2S—H2SB106.1 (16)
C19—C14—S1128.78 (15)Cl3S—C2S—H2SB108.2 (16)
C15—C14—S1109.46 (14)H2SA—C2S—H2SB115 (2)
C11—N1—C1—C20.4 (3)C14—S1—C13—N3−0.46 (15)
C11—N1—C1—C13−179.31 (15)C14—S1—C13—C1178.90 (14)
N1—C1—C2—C30.9 (3)C13—S1—C14—C19−179.45 (19)
C13—C1—C2—C3−179.40 (16)C13—S1—C14—C150.63 (14)
C1—C2—C3—C4−1.3 (3)C13—N3—C15—C16−179.48 (19)
C2—C3—C4—C110.5 (3)C13—N3—C15—C140.4 (2)
C2—C3—C4—C5−177.33 (17)C19—C14—C15—N3179.34 (17)
C3—C4—C5—C6175.55 (18)S1—C14—C15—N3−0.7 (2)
C11—C4—C5—C6−2.2 (3)C19—C14—C15—C16−0.8 (3)
C4—C5—C6—C71.5 (3)S1—C14—C15—C16179.16 (15)
C5—C6—C7—C8−177.99 (17)N3—C15—C16—C17−179.27 (19)
C5—C6—C7—C121.3 (3)C14—C15—C16—C170.8 (3)
C12—C7—C8—C91.7 (3)C15—C16—C17—C18−0.4 (3)
C6—C7—C8—C9−179.01 (17)C16—C17—C18—C19−0.2 (3)
C7—C8—C9—C100.3 (3)C17—C18—C19—C140.3 (3)
C12—N2—C10—C91.2 (2)C15—C14—C19—C180.2 (3)
C12—N2—C10—C20−179.38 (15)S1—C14—C19—C18−179.70 (16)
C8—C9—C10—N2−1.8 (3)C22—N4—C20—C10178.79 (16)
C8—C9—C10—C20178.81 (16)C22—N4—C20—S2−0.35 (19)
C1—N1—C11—C4−1.3 (2)N2—C10—C20—N4178.51 (16)
C1—N1—C11—C12177.38 (16)C9—C10—C20—N4−2.1 (3)
C3—C4—C11—N10.9 (3)N2—C10—C20—S2−2.4 (2)
C5—C4—C11—N1178.72 (16)C9—C10—C20—S2177.03 (13)
C3—C4—C11—C12−177.81 (16)C21—S2—C20—N40.89 (14)
C5—C4—C11—C120.0 (2)C21—S2—C20—C10−178.30 (14)
C10—N2—C12—C70.9 (2)C20—S2—C21—C26177.75 (18)
C10—N2—C12—C11−177.37 (15)C20—S2—C21—C22−1.12 (13)
C8—C7—C12—N2−2.3 (3)C20—N4—C22—C23−178.48 (17)
C6—C7—C12—N2178.33 (16)C20—N4—C22—C21−0.6 (2)
C8—C7—C12—C11175.94 (16)C26—C21—C22—N4−177.75 (16)
C6—C7—C12—C11−3.4 (2)S2—C21—C22—N41.22 (19)
N1—C11—C12—N22.3 (2)C26—C21—C22—C230.3 (3)
C4—C11—C12—N2−178.98 (15)S2—C21—C22—C23179.26 (14)
N1—C11—C12—C7−176.04 (15)N4—C22—C23—C24178.07 (17)
C4—C11—C12—C72.7 (2)C21—C22—C23—C240.3 (3)
C15—N3—C13—C1−179.20 (16)C22—C23—C24—C25−0.8 (3)
C15—N3—C13—S10.1 (2)C23—C24—C25—C260.8 (3)
N1—C1—C13—N3−170.20 (17)C24—C25—C26—C21−0.2 (3)
C2—C1—C13—N310.1 (3)C22—C21—C26—C25−0.3 (3)
N1—C1—C13—S110.5 (2)S2—C21—C26—C25−179.07 (15)
C2—C1—C13—S1−169.22 (14)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C1S—H1SB···N4i0.94 (2)2.44 (2)3.360 (3)166.7 (19)
C3—H3···Cl1Sii0.92 (2)2.82 (2)3.615 (2)145.6 (16)

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB2737).

References

  • Bruker (2005). APEX2, SAINT, SADABS, XP and XCIF Bruker AXS Inc., Madison, Wisconsin, USA.
  • Gude, L., Fernandez, M. J., Grant, K. B. & Loernte, A. (2005). Org. Biomol. Chem.3, 1856–1862. [PubMed]
  • Kerbs, F. C. (2003). Tetrahedron Lett.44, 6643–6646.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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