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Acta Cryst. (2008). E64, o408    [ doi:10.1107/S1600536807068729 ]

1-{2-[(Anthracen-10-yl)methyleneamino]phenyl}-3-phenylthiourea

D. Gayathri, D. Velmurugan, K. Ravikumar, S. Devaraj and M. Kandaswamy

Abstract top

The title compound, C28H21N3S, crystallizes with two molecules in the asymmetric unit. There are only very slight differences in the torsion angles between the two molecules. The two molecules are stabilized by intramolecular N-H...N interactions and the crystal packing is stabilized by intermolecular N-H...S interactions.

Comment top

The design and synthesis of anion receptors possessing high affinity and selectivity represents a challenge that continues to attract considerable attention within the molecular recognition and supramolecular chemistry communities due to the important role anions play in areas as diverse as the environment and medicine (Lee et al., 2005). Of particular interest in this regard are colorimetric anion sensors and fluoresecent chemosensors for anions. Recent efforts to investigate anion binding by naked eye detection (Lee et al., 2003) and through flouresencent changes (Yoon et al., 2004) may provide important results. The most desirable property of an anion sensor based on fluoresecence is the ability to respond to applied perturbation in a highly selective and sensitive manner by dramatic change in emission colour and/or intensity.

The title compound crystallizes in triclinic system with two molecules in asymmetric unit. The bond lengths, bond angles and torsion angles of the title compound are comparable with the similar structure solved earlier (Gayathri et al., 2007). The dihedral angle between the phenyl rings C1–C6 and C8–C13 in molecule A and between C29–C34 and C36–C41 in molecule B are 18.3 (1) and 20.0 (1)°, respectively. The acenapthene moiety in both the molecules are planar as analysed based on the dihedral angles between the rings in the acenapthene moiety.

The two molecules are stabilized by N—H···N intramolecular interactions generating S(5) motif. The crystal packing is stabilized by N—H···S intermolecular interactions generating centrosymmetric dimer of R22(8) ring.

Related literature top

For related literature, see: Lee et al. (2003, 2005); Gayathri et al. (2007); Yoon et al. (2004).

Experimental top

The compound 1-(2-((anthracene-10-yl)methyleneamino)phenyl)-3-phenylthiourea was synthesized by Schiff base condensation between1-(2-aminophenyl)-3-phenyl thiourea and 9-anthraldehyde. To the solution of 1-(2-aminophenyl)-3-phenyl thiourea (0.5 g, 2.05 mmol) in methanol (25 ml), 4-nitrobenzaldehyde (0.424 g, 2.05 mmol) in methanol was added under stirring. The resulting mixture was heated at reflux for 3 h and cooled to room temperature. The solid product was collected by filtration and washed with cold methanol. The microcrystalline compound was recrystallized from hot acetonitrile; yellow coloured crystals suitable for X ray diffraction were obtained on slow evaporation [yield 82.9%,; m.p.: 453 K]

Refinement top

All H-atoms were refined using a riding model with C—H = 0.93Å and N—H = 0.86 Å with Uiso(H)=1.2Ueq (C,N).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PARST (Nardelli, 1995).

Figures top
[Figure 1] Fig. 1. The molecular structure of title compound, showing 30% probability displacement ellipsoids.
[Figure 2] Fig. 2. The molecular packing of (I), viewed down the a axis.
1-{2-[(Anthracen-10-yl)methyleneamino]phenyl}-3-phenylthiourea top
Crystal data top
C28H21N3SZ = 4
Mr = 431.54F000 = 904
Triclinic, P1Dx = 1.323 Mg m−3
Hall symbol: -P 1Mo Kα radiation
λ = 0.71073 Å
a = 6.6148 (6) ÅCell parameters from 4967 reflections
b = 14.3154 (12) Åθ = 0.9–25.0º
c = 23.823 (2) ŵ = 0.17 mm−1
α = 74.045 (1)ºT = 293 (2) K
β = 88.705 (1)ºBlock, orange
γ = 87.421 (1)º0.27 × 0.25 × 0.20 mm
V = 2166.7 (3) Å3
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer		7972 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.019
Monochromator: graphiteθmax = 28.0º
T = 293(2) Kθmin = 0.9º
ω scansh = −8→8
Absorption correction: nonek = −18→18
25075 measured reflectionsl = −31→30
9927 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.047H-atom parameters constrained
wR(F2) = 0.133  w = 1/[σ2(Fo2) + (0.0719P)2 + 0.4912P]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.001
9927 reflectionsΔρmax = 0.30 e Å−3
577 parametersΔρmin = −0.18 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
C28H21N3Sγ = 87.421 (1)º
Mr = 431.54V = 2166.7 (3) Å3
Triclinic, P1Z = 4
a = 6.6148 (6) ÅMo Kα
b = 14.3154 (12) ŵ = 0.17 mm−1
c = 23.823 (2) ÅT = 293 (2) K
α = 74.045 (1)º0.27 × 0.25 × 0.20 mm
β = 88.705 (1)º
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer		9927 independent reflections
Absorption correction: none7972 reflections with I > 2σ(I)
25075 measured reflectionsRint = 0.019
Refinement top
R[F2 > 2σ(F2)] = 0.047577 parameters
wR(F2) = 0.133H-atom parameters constrained
S = 1.01Δρmax = 0.30 e Å−3
9927 reflectionsΔρmin = −0.18 e Å−3
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
C11.0750 (3)0.83551 (13)0.43543 (8)0.0668 (5)
H10.94280.85120.42260.080*
C21.2051 (4)0.90827 (15)0.43618 (9)0.0824 (7)
H21.16040.97300.42270.099*
C31.4005 (4)0.88623 (17)0.45663 (9)0.0757 (6)
H31.48740.93570.45630.091*
C41.4646 (3)0.79053 (17)0.47747 (9)0.0661 (5)
H41.59370.77500.49280.079*
C51.3389 (3)0.71766 (14)0.47575 (8)0.0549 (4)
H51.38470.65310.48930.066*
C61.1435 (2)0.73914 (12)0.45391 (6)0.0453 (3)
C70.8606 (2)0.64513 (10)0.42670 (7)0.0407 (3)
C80.6251 (2)0.73651 (10)0.34664 (6)0.0388 (3)
C90.4771 (3)0.67024 (12)0.34774 (7)0.0499 (4)
H90.49530.60610.37000.060*
C100.3022 (3)0.69976 (13)0.31565 (8)0.0533 (4)
H100.20260.65530.31720.064*
C110.2736 (3)0.79363 (13)0.28152 (8)0.0548 (4)
H110.15440.81290.26080.066*
C120.4229 (3)0.85882 (12)0.27830 (8)0.0529 (4)
H120.40540.92190.25440.063*
C130.5993 (2)0.83184 (10)0.31016 (7)0.0405 (3)
C140.7895 (2)0.96526 (11)0.26658 (7)0.0455 (4)
H140.72020.96970.23230.055*
C150.9408 (2)1.03762 (10)0.26697 (7)0.0414 (3)
C161.0866 (2)1.05835 (10)0.22175 (7)0.0428 (3)
C171.0824 (3)1.02141 (12)0.17182 (8)0.0554 (4)
H170.97500.98450.16730.067*
C181.2331 (4)1.03941 (15)0.13084 (9)0.0704 (6)
H181.22631.01530.09850.084*
C191.3993 (4)1.09424 (16)0.13679 (10)0.0738 (6)
H191.50291.10440.10900.089*
C201.4083 (3)1.13178 (13)0.18254 (9)0.0627 (5)
H201.51781.16850.18570.075*
C211.2538 (2)1.11652 (11)0.22630 (7)0.0473 (4)
C221.2633 (3)1.15498 (11)0.27368 (8)0.0527 (4)
H221.37401.19080.27700.063*
C231.1118 (3)1.14130 (11)0.31620 (7)0.0512 (4)
C241.1149 (4)1.18661 (14)0.36275 (9)0.0726 (6)
H241.22391.22350.36610.087*
C250.9601 (5)1.17627 (17)0.40198 (10)0.0892 (8)
H250.96391.20600.43210.107*
C260.7947 (5)1.12125 (17)0.39754 (10)0.0862 (7)
H260.68771.11670.42400.103*
C270.7874 (3)1.07436 (14)0.35527 (9)0.0640 (5)
H270.67741.03690.35390.077*
C280.9462 (3)1.08186 (11)0.31304 (7)0.0464 (4)
C290.8250 (2)0.82162 (12)0.11334 (8)0.0498 (4)
H290.88000.87070.08360.060*
C300.9403 (3)0.77475 (14)0.16104 (9)0.0596 (5)
H301.07220.79310.16360.071*
C310.8624 (3)0.70121 (14)0.20488 (9)0.0660 (5)
H310.94130.66930.23680.079*
C320.6657 (3)0.67491 (14)0.20117 (8)0.0663 (5)
H320.61300.62460.23060.080*
C330.5464 (3)0.72254 (13)0.15422 (7)0.0564 (4)
H330.41300.70560.15260.068*
C340.6266 (2)0.79581 (11)0.10948 (7)0.0423 (3)
C350.3493 (2)0.83579 (10)0.03364 (6)0.0393 (3)
C360.1103 (2)0.70265 (10)0.03509 (6)0.0372 (3)
C37−0.0307 (2)0.74808 (12)−0.00702 (7)0.0469 (4)
H37−0.00830.8100−0.03110.056*
C38−0.2040 (3)0.70172 (13)−0.01336 (8)0.0531 (4)
H38−0.29790.7331−0.04150.064*
C39−0.2395 (3)0.61000 (14)0.02130 (8)0.0615 (5)
H39−0.35700.57940.01700.074*
C40−0.0983 (3)0.56365 (13)0.06269 (8)0.0586 (5)
H40−0.12090.50110.08590.070*
C410.0756 (2)0.60844 (11)0.07029 (6)0.0411 (3)
C420.1800 (2)0.50230 (11)0.15842 (7)0.0450 (3)
H420.04370.49500.16830.054*
C430.3335 (2)0.44540 (10)0.19903 (7)0.0427 (3)
C440.3104 (3)0.43694 (11)0.25943 (7)0.0473 (4)
C450.1310 (3)0.46802 (12)0.28476 (8)0.0593 (5)
H450.02160.49480.26100.071*
C460.1176 (4)0.45915 (14)0.34297 (9)0.0736 (6)
H46−0.00250.47770.35870.088*
C470.2841 (5)0.42199 (16)0.37991 (9)0.0795 (7)
H470.27480.41900.41940.095*
C480.4553 (4)0.39112 (15)0.35819 (8)0.0699 (6)
H480.56330.36690.38310.084*
C490.4761 (3)0.39443 (12)0.29795 (7)0.0545 (4)
C500.6473 (3)0.35753 (13)0.27574 (8)0.0573 (5)
H500.75550.33310.30050.069*
C510.6633 (2)0.35574 (11)0.21783 (7)0.0500 (4)
C520.8315 (3)0.30881 (13)0.19662 (9)0.0620 (5)
H520.93890.28300.22140.074*
C530.8381 (3)0.30117 (14)0.14154 (10)0.0660 (5)
H530.94870.26990.12870.079*
C540.6768 (3)0.34067 (13)0.10326 (9)0.0587 (4)
H540.67960.33290.06580.070*
C550.5179 (3)0.38982 (11)0.12048 (7)0.0486 (4)
H550.41620.41730.09400.058*
C560.5029 (2)0.40045 (10)0.17814 (7)0.0426 (3)
N11.0247 (2)0.65807 (9)0.45631 (6)0.0500 (3)
H1A1.06550.60610.48200.060*
N20.8043 (2)0.71818 (9)0.38004 (6)0.0456 (3)
H2A0.89320.76160.36840.055*
N30.75168 (19)0.89754 (9)0.31147 (6)0.0452 (3)
N40.5165 (2)0.85242 (9)0.06068 (6)0.0485 (3)
H4A0.56540.90840.04520.058*
N50.29052 (19)0.74304 (9)0.04688 (6)0.0436 (3)
H5A0.37860.70090.06590.052*
N60.22933 (19)0.56134 (9)0.11000 (6)0.0435 (3)
S10.74429 (7)0.53913 (3)0.45046 (2)0.05533 (13)
S20.23302 (6)0.93114 (3)−0.01346 (2)0.05342 (13)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0887 (14)0.0436 (9)0.0634 (11)−0.0040 (9)−0.0342 (10)−0.0039 (8)
C20.132 (2)0.0445 (10)0.0649 (12)−0.0186 (12)−0.0358 (13)−0.0002 (9)
C30.1011 (17)0.0719 (14)0.0559 (11)−0.0431 (13)−0.0029 (11)−0.0140 (10)
C40.0545 (11)0.0793 (14)0.0698 (12)−0.0173 (10)0.0013 (9)−0.0274 (11)
C50.0492 (9)0.0562 (10)0.0595 (10)−0.0036 (8)−0.0024 (8)−0.0156 (8)
C60.0528 (9)0.0423 (8)0.0377 (8)−0.0060 (7)−0.0069 (6)−0.0045 (6)
C70.0406 (7)0.0336 (7)0.0435 (8)0.0008 (6)−0.0049 (6)−0.0032 (6)
C80.0415 (7)0.0345 (7)0.0373 (7)−0.0041 (6)−0.0073 (6)−0.0038 (6)
C90.0583 (10)0.0373 (8)0.0486 (9)−0.0115 (7)−0.0134 (7)−0.0002 (7)
C100.0507 (9)0.0484 (9)0.0589 (10)−0.0162 (7)−0.0136 (7)−0.0083 (8)
C110.0455 (9)0.0490 (9)0.0672 (11)−0.0035 (7)−0.0212 (8)−0.0092 (8)
C120.0500 (9)0.0354 (8)0.0672 (11)−0.0011 (7)−0.0186 (8)−0.0025 (7)
C130.0406 (7)0.0329 (7)0.0457 (8)−0.0040 (6)−0.0078 (6)−0.0055 (6)
C140.0452 (8)0.0364 (7)0.0498 (9)−0.0024 (6)−0.0141 (7)−0.0021 (6)
C150.0448 (8)0.0279 (6)0.0455 (8)−0.0017 (6)−0.0099 (6)0.0007 (6)
C160.0477 (8)0.0284 (7)0.0458 (8)0.0022 (6)−0.0096 (6)0.0009 (6)
C170.0681 (11)0.0430 (9)0.0516 (10)0.0030 (8)−0.0110 (8)−0.0069 (7)
C180.0955 (16)0.0606 (12)0.0484 (10)0.0151 (11)0.0003 (10)−0.0065 (9)
C190.0757 (14)0.0616 (12)0.0665 (13)0.0092 (11)0.0179 (11)0.0087 (10)
C200.0554 (10)0.0448 (9)0.0731 (13)−0.0020 (8)0.0060 (9)0.0082 (9)
C210.0471 (8)0.0304 (7)0.0549 (9)−0.0010 (6)−0.0060 (7)0.0046 (6)
C220.0544 (9)0.0330 (7)0.0645 (10)−0.0110 (7)−0.0154 (8)−0.0003 (7)
C230.0677 (11)0.0318 (7)0.0502 (9)−0.0048 (7)−0.0142 (8)−0.0034 (7)
C240.1128 (18)0.0435 (10)0.0621 (12)−0.0131 (11)−0.0221 (12)−0.0124 (9)
C250.156 (3)0.0593 (13)0.0565 (12)−0.0048 (15)−0.0014 (15)−0.0237 (10)
C260.129 (2)0.0610 (13)0.0683 (14)−0.0083 (14)0.0262 (14)−0.0183 (11)
C270.0812 (13)0.0460 (10)0.0611 (11)−0.0065 (9)0.0113 (10)−0.0086 (8)
C280.0571 (9)0.0305 (7)0.0460 (8)−0.0021 (6)−0.0057 (7)−0.0007 (6)
C290.0455 (9)0.0467 (9)0.0562 (10)−0.0021 (7)−0.0099 (7)−0.0116 (7)
C300.0490 (9)0.0618 (11)0.0711 (12)0.0055 (8)−0.0229 (8)−0.0231 (10)
C310.0815 (13)0.0551 (11)0.0612 (11)0.0114 (10)−0.0356 (10)−0.0150 (9)
C320.0912 (15)0.0551 (11)0.0465 (10)−0.0107 (10)−0.0176 (9)−0.0009 (8)
C330.0576 (10)0.0574 (10)0.0483 (9)−0.0124 (8)−0.0103 (8)−0.0025 (8)
C340.0426 (8)0.0373 (7)0.0453 (8)0.0005 (6)−0.0106 (6)−0.0079 (6)
C350.0352 (7)0.0360 (7)0.0416 (7)−0.0021 (6)−0.0029 (6)−0.0020 (6)
C360.0371 (7)0.0351 (7)0.0370 (7)−0.0019 (6)−0.0050 (5)−0.0054 (6)
C370.0505 (9)0.0402 (8)0.0446 (8)−0.0025 (7)−0.0131 (7)−0.0014 (6)
C380.0500 (9)0.0536 (10)0.0511 (9)−0.0028 (7)−0.0204 (7)−0.0050 (8)
C390.0524 (10)0.0588 (11)0.0668 (11)−0.0167 (8)−0.0214 (8)−0.0028 (9)
C400.0595 (10)0.0439 (9)0.0632 (11)−0.0145 (8)−0.0194 (8)0.0044 (8)
C410.0422 (8)0.0354 (7)0.0423 (8)−0.0016 (6)−0.0088 (6)−0.0042 (6)
C420.0443 (8)0.0364 (7)0.0496 (9)−0.0059 (6)−0.0089 (7)−0.0027 (6)
C430.0488 (8)0.0301 (7)0.0445 (8)−0.0099 (6)−0.0111 (6)−0.0003 (6)
C440.0624 (10)0.0293 (7)0.0474 (8)−0.0131 (7)−0.0077 (7)−0.0033 (6)
C450.0802 (13)0.0384 (8)0.0576 (10)−0.0085 (8)−0.0003 (9)−0.0093 (8)
C460.1098 (18)0.0483 (10)0.0660 (13)−0.0177 (11)0.0168 (12)−0.0202 (9)
C470.139 (2)0.0554 (12)0.0477 (11)−0.0326 (13)−0.0053 (13)−0.0151 (9)
C480.1050 (17)0.0554 (11)0.0480 (10)−0.0246 (11)−0.0185 (11)−0.0072 (9)
C490.0767 (12)0.0377 (8)0.0451 (9)−0.0212 (8)−0.0178 (8)−0.0003 (7)
C500.0595 (10)0.0477 (9)0.0557 (10)−0.0130 (8)−0.0242 (8)0.0044 (8)
C510.0485 (9)0.0358 (8)0.0562 (10)−0.0107 (7)−0.0150 (7)0.0060 (7)
C520.0464 (9)0.0461 (9)0.0779 (13)−0.0008 (7)−0.0127 (8)0.0099 (9)
C530.0557 (11)0.0487 (10)0.0820 (14)0.0014 (8)0.0086 (10)−0.0001 (9)
C540.0654 (11)0.0454 (9)0.0600 (11)−0.0072 (8)0.0055 (9)−0.0053 (8)
C550.0531 (9)0.0383 (8)0.0486 (9)−0.0064 (7)−0.0064 (7)−0.0011 (7)
C560.0452 (8)0.0287 (7)0.0472 (8)−0.0089 (6)−0.0111 (6)0.0027 (6)
N10.0529 (8)0.0357 (6)0.0524 (8)−0.0039 (6)−0.0181 (6)0.0048 (6)
N20.0462 (7)0.0360 (6)0.0461 (7)−0.0118 (5)−0.0124 (5)0.0054 (5)
N30.0439 (7)0.0313 (6)0.0547 (8)−0.0045 (5)−0.0142 (6)−0.0009 (5)
N40.0442 (7)0.0377 (7)0.0549 (8)−0.0094 (5)−0.0144 (6)0.0042 (6)
N50.0390 (6)0.0337 (6)0.0508 (7)−0.0011 (5)−0.0137 (5)0.0015 (5)
N60.0452 (7)0.0324 (6)0.0471 (7)−0.0041 (5)−0.0120 (5)0.0001 (5)
S10.0498 (2)0.0344 (2)0.0690 (3)−0.00536 (16)−0.01566 (19)0.00915 (18)
S20.0460 (2)0.0368 (2)0.0651 (3)−0.00503 (16)−0.01748 (18)0.00861 (18)
Geometric parameters (Å, °) top
C1—C21.385 (3)C29—H290.9300
C1—C61.386 (2)C30—C311.373 (3)
C1—H10.9300C30—H300.9300
C2—C31.384 (3)C31—C321.382 (3)
C2—H20.9300C31—H310.9300
C3—C41.373 (3)C32—C331.382 (2)
C3—H30.9300C32—H320.9300
C4—C51.373 (3)C33—C341.388 (2)
C4—H40.9300C33—H330.9300
C5—C61.393 (2)C34—N41.4164 (18)
C5—H50.9300C35—N51.3506 (19)
C6—N11.418 (2)C35—N41.3545 (19)
C7—N21.3462 (18)C35—S21.6782 (14)
C7—N11.354 (2)C36—C371.3884 (19)
C7—S11.6818 (15)C36—C411.404 (2)
C8—C91.389 (2)C36—N51.4146 (18)
C8—C131.4073 (19)C37—C381.382 (2)
C8—N21.4164 (18)C37—H370.9300
C9—C101.385 (2)C38—C391.373 (2)
C9—H90.9300C38—H380.9300
C10—C111.373 (2)C39—C401.382 (2)
C10—H100.9300C39—H390.9300
C11—C121.376 (2)C40—C411.381 (2)
C11—H110.9300C40—H400.9300
C12—C131.387 (2)C41—N61.4192 (18)
C12—H120.9300C42—N61.274 (2)
C13—N31.4159 (18)C42—C431.472 (2)
C14—N31.259 (2)C42—H420.9300
C14—C151.475 (2)C43—C561.415 (2)
C14—H140.9300C43—C441.416 (2)
C15—C161.408 (2)C44—C451.427 (3)
C15—C281.412 (2)C44—C491.446 (2)
C16—C171.430 (2)C45—C461.359 (3)
C16—C211.437 (2)C45—H450.9300
C17—C181.361 (3)C46—C471.416 (3)
C17—H170.9300C46—H460.9300
C18—C191.411 (3)C47—C481.341 (3)
C18—H180.9300C47—H470.9300
C19—C201.345 (3)C48—C491.427 (3)
C19—H190.9300C48—H480.9300
C20—C211.423 (3)C49—C501.384 (3)
C20—H200.9300C50—C511.388 (3)
C21—C221.389 (3)C50—H500.9300
C22—C231.390 (3)C51—C521.428 (3)
C22—H220.9300C51—C561.443 (2)
C23—C241.431 (3)C52—C531.346 (3)
C23—C281.432 (2)C52—H520.9300
C24—C251.356 (4)C53—C541.412 (3)
C24—H240.9300C53—H530.9300
C25—C261.399 (4)C54—C551.357 (3)
C25—H250.9300C54—H540.9300
C26—C271.358 (3)C55—C561.424 (2)
C26—H260.9300C55—H550.9300
C27—C281.425 (3)N1—H1A0.8600
C27—H270.9300N2—H2A0.8600
C29—C301.377 (2)N4—H4A0.8600
C29—C341.391 (2)N5—H5A0.8600
C2—C1—C6119.44 (19)C30—C31—H31120.3
C2—C1—H1120.3C32—C31—H31120.3
C6—C1—H1120.3C31—C32—C33120.71 (18)
C3—C2—C1121.1 (2)C31—C32—H32119.6
C3—C2—H2119.5C33—C32—H32119.6
C1—C2—H2119.5C32—C33—C34119.71 (17)
C4—C3—C2119.27 (19)C32—C33—H33120.1
C4—C3—H3120.4C34—C33—H33120.1
C2—C3—H3120.4C33—C34—C29119.27 (15)
C5—C4—C3120.3 (2)C33—C34—N4124.68 (14)
C5—C4—H4119.9C29—C34—N4115.92 (14)
C3—C4—H4119.9N5—C35—N4116.82 (13)
C4—C5—C6120.85 (18)N5—C35—S2125.39 (11)
C4—C5—H5119.6N4—C35—S2117.79 (11)
C6—C5—H5119.6C37—C36—C41119.01 (13)
C1—C6—C5118.99 (16)C37—C36—N5125.81 (13)
C1—C6—N1124.94 (16)C41—C36—N5115.19 (12)
C5—C6—N1115.92 (14)C38—C37—C36120.32 (14)
N2—C7—N1117.21 (13)C38—C37—H37119.8
N2—C7—S1125.02 (12)C36—C37—H37119.8
N1—C7—S1117.76 (11)C39—C38—C37120.89 (15)
C9—C8—C13118.98 (13)C39—C38—H38119.6
C9—C8—N2126.00 (13)C37—C38—H38119.6
C13—C8—N2115.01 (12)C38—C39—C40119.14 (16)
C10—C9—C8119.98 (14)C38—C39—H39120.4
C10—C9—H9120.0C40—C39—H39120.4
C8—C9—H9120.0C41—C40—C39121.25 (16)
C11—C10—C9121.11 (15)C41—C40—H40119.4
C11—C10—H10119.4C39—C40—H40119.4
C9—C10—H10119.4C40—C41—C36119.38 (13)
C10—C11—C12119.34 (15)C40—C41—N6122.91 (13)
C10—C11—H11120.3C36—C41—N6117.60 (13)
C12—C11—H11120.3N6—C42—C43121.60 (15)
C11—C12—C13121.02 (15)N6—C42—H42119.2
C11—C12—H12119.5C43—C42—H42119.2
C13—C12—H12119.5C56—C43—C44120.31 (14)
C12—C13—C8119.47 (13)C56—C43—C42120.68 (14)
C12—C13—N3123.33 (13)C44—C43—C42119.00 (15)
C8—C13—N3117.03 (12)C43—C44—C45123.47 (16)
N3—C14—C15121.62 (14)C43—C44—C49118.77 (16)
N3—C14—H14119.2C45—C44—C49117.76 (16)
C15—C14—H14119.2C46—C45—C44121.1 (2)
C16—C15—C28120.45 (14)C46—C45—H45119.5
C16—C15—C14118.51 (14)C44—C45—H45119.5
C28—C15—C14120.97 (14)C45—C46—C47120.8 (2)
C15—C16—C17123.43 (15)C45—C46—H46119.6
C15—C16—C21119.14 (15)C47—C46—H46119.6
C17—C16—C21117.39 (15)C48—C47—C46120.2 (2)
C18—C17—C16121.09 (18)C48—C47—H47119.9
C18—C17—H17119.5C46—C47—H47119.9
C16—C17—H17119.5C47—C48—C49121.7 (2)
C17—C18—C19120.9 (2)C47—C48—H48119.1
C17—C18—H18119.6C49—C48—H48119.1
C19—C18—H18119.6C50—C49—C48122.22 (18)
C20—C19—C18120.17 (19)C50—C49—C44119.51 (15)
C20—C19—H19119.9C48—C49—C44118.3 (2)
C18—C19—H19119.9C49—C50—C51122.32 (15)
C19—C20—C21121.42 (19)C49—C50—H50118.8
C19—C20—H20119.3C51—C50—H50118.8
C21—C20—H20119.3C50—C51—C52121.97 (16)
C22—C21—C20121.45 (17)C50—C51—C56119.13 (17)
C22—C21—C16119.52 (15)C52—C51—C56118.88 (16)
C20—C21—C16119.02 (17)C53—C52—C51121.42 (17)
C21—C22—C23121.73 (15)C53—C52—H52119.3
C21—C22—H22119.1C51—C52—H52119.3
C23—C22—H22119.1C52—C53—C54119.96 (18)
C22—C23—C24121.61 (18)C52—C53—H53120.0
C22—C23—C28119.49 (15)C54—C53—H53120.0
C24—C23—C28118.89 (18)C55—C54—C53120.86 (19)
C25—C24—C23120.5 (2)C55—C54—H54119.6
C25—C24—H24119.7C53—C54—H54119.6
C23—C24—H24119.7C54—C55—C56121.67 (16)
C24—C25—C26120.5 (2)C54—C55—H55119.2
C24—C25—H25119.7C56—C55—H55119.2
C26—C25—H25119.7C43—C56—C55123.44 (14)
C27—C26—C25121.2 (2)C43—C56—C51119.30 (15)
C27—C26—H26119.4C55—C56—C51117.07 (15)
C25—C26—H26119.4C7—N1—C6133.57 (13)
C26—C27—C28120.8 (2)C7—N1—H1A113.2
C26—C27—H27119.6C6—N1—H1A113.2
C28—C27—H27119.6C7—N2—C8131.67 (13)
C15—C28—C27122.69 (16)C7—N2—H2A114.2
C15—C28—C23119.31 (15)C8—N2—H2A114.2
C27—C28—C23117.91 (16)C14—N3—C13120.04 (13)
C30—C29—C34120.22 (17)C35—N4—C34132.70 (13)
C30—C29—H29119.9C35—N4—H4A113.6
C34—C29—H29119.9C34—N4—H4A113.6
C31—C30—C29120.60 (17)C35—N5—C36131.68 (12)
C31—C30—H30119.7C35—N5—H5A114.2
C29—C30—H30119.7C36—N5—H5A114.2
C30—C31—C32119.46 (17)C42—N6—C41119.36 (13)
C6—C1—C2—C3−1.9 (3)C37—C38—C39—C40−0.5 (3)
C1—C2—C3—C4−1.2 (3)C38—C39—C40—C410.9 (3)
C2—C3—C4—C52.7 (3)C39—C40—C41—C36−0.3 (3)
C3—C4—C5—C6−1.2 (3)C39—C40—C41—N6−176.40 (18)
C2—C1—C6—C53.4 (3)C37—C36—C41—C40−0.7 (2)
C2—C1—C6—N1178.75 (19)N5—C36—C41—C40178.87 (15)
C4—C5—C6—C1−1.9 (3)C37—C36—C41—N6175.57 (14)
C4—C5—C6—N1−177.70 (17)N5—C36—C41—N6−4.9 (2)
C13—C8—C9—C10−3.4 (3)N6—C42—C43—C56−43.0 (2)
N2—C8—C9—C10175.63 (16)N6—C42—C43—C44136.46 (16)
C8—C9—C10—C111.3 (3)C56—C43—C44—C45−170.72 (14)
C9—C10—C11—C121.3 (3)C42—C43—C44—C459.9 (2)
C10—C11—C12—C13−1.7 (3)C56—C43—C44—C499.1 (2)
C11—C12—C13—C8−0.4 (3)C42—C43—C44—C49−170.34 (13)
C11—C12—C13—N3−175.68 (17)C43—C44—C45—C46−179.29 (16)
C9—C8—C13—C123.0 (2)C49—C44—C45—C460.9 (2)
N2—C8—C13—C12−176.15 (15)C44—C45—C46—C472.3 (3)
C9—C8—C13—N3178.55 (15)C45—C46—C47—C48−2.8 (3)
N2—C8—C13—N3−0.6 (2)C46—C47—C48—C490.0 (3)
N3—C14—C15—C16131.51 (17)C47—C48—C49—C50−176.09 (18)
N3—C14—C15—C28−45.5 (2)C47—C48—C49—C443.2 (3)
C28—C15—C16—C17−175.64 (14)C43—C44—C49—C50−4.1 (2)
C14—C15—C16—C177.4 (2)C45—C44—C49—C50175.73 (15)
C28—C15—C16—C216.8 (2)C43—C44—C49—C48176.64 (15)
C14—C15—C16—C21−170.17 (13)C45—C44—C49—C48−3.5 (2)
C15—C16—C17—C18−176.45 (16)C48—C49—C50—C51176.32 (16)
C21—C16—C17—C181.1 (2)C44—C49—C50—C51−2.9 (2)
C16—C17—C18—C190.7 (3)C49—C50—C51—C52−173.56 (15)
C17—C18—C19—C20−1.8 (3)C49—C50—C51—C564.9 (2)
C18—C19—C20—C210.8 (3)C50—C51—C52—C53174.92 (17)
C19—C20—C21—C22179.76 (17)C56—C51—C52—C53−3.5 (2)
C19—C20—C21—C161.0 (3)C51—C52—C53—C540.5 (3)
C15—C16—C21—C22−3.1 (2)C52—C53—C54—C552.6 (3)
C17—C16—C21—C22179.26 (14)C53—C54—C55—C56−2.4 (3)
C15—C16—C21—C20175.70 (14)C44—C43—C56—C55167.66 (14)
C17—C16—C21—C20−2.0 (2)C42—C43—C56—C55−12.9 (2)
C20—C21—C22—C23179.24 (15)C44—C43—C56—C51−7.2 (2)
C16—C21—C22—C23−2.0 (2)C42—C43—C56—C51172.21 (13)
C21—C22—C23—C24−175.56 (16)C54—C55—C56—C43−175.61 (15)
C21—C22—C23—C283.3 (2)C54—C55—C56—C51−0.6 (2)
C22—C23—C24—C25176.57 (19)C50—C51—C56—C430.2 (2)
C28—C23—C24—C25−2.3 (3)C52—C51—C56—C43178.72 (14)
C23—C24—C25—C26−0.1 (4)C50—C51—C56—C55−174.95 (14)
C24—C25—C26—C272.2 (4)C52—C51—C56—C553.5 (2)
C25—C26—C27—C28−1.7 (3)N2—C7—N1—C69.4 (3)
C16—C15—C28—C27170.93 (15)S1—C7—N1—C6−171.10 (15)
C14—C15—C28—C27−12.2 (2)C1—C6—N1—C726.5 (3)
C16—C15—C28—C23−5.6 (2)C5—C6—N1—C7−157.95 (18)
C14—C15—C28—C23171.36 (14)N1—C7—N2—C8−166.81 (16)
C26—C27—C28—C15−177.34 (18)S1—C7—N2—C813.8 (3)
C26—C27—C28—C23−0.8 (3)C9—C8—N2—C7−14.2 (3)
C22—C23—C28—C150.5 (2)C13—C8—N2—C7164.89 (16)
C24—C23—C28—C15179.40 (15)C15—C14—N3—C13177.32 (14)
C22—C23—C28—C27−176.18 (15)C12—C13—N3—C14−34.9 (2)
C24—C23—C28—C272.7 (2)C8—C13—N3—C14149.78 (16)
C34—C29—C30—C311.0 (3)N5—C35—N4—C34−14.2 (3)
C29—C30—C31—C32−0.7 (3)S2—C35—N4—C34165.96 (15)
C30—C31—C32—C33−0.7 (3)C33—C34—N4—C35−25.0 (3)
C31—C32—C33—C341.8 (3)C29—C34—N4—C35159.31 (17)
C32—C33—C34—C29−1.4 (3)N4—C35—N5—C36167.90 (15)
C32—C33—C34—N4−177.02 (17)S2—C35—N5—C36−12.3 (3)
C30—C29—C34—C330.1 (3)C37—C36—N5—C3518.4 (3)
C30—C29—C34—N4176.05 (16)C41—C36—N5—C35−161.10 (16)
C41—C36—C37—C381.1 (2)C43—C42—N6—C41174.85 (14)
N5—C36—C37—C38−178.38 (15)C40—C41—N6—C42−36.1 (2)
C36—C37—C38—C39−0.5 (3)C36—C41—N6—C42147.81 (15)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···S1i0.862.553.399 (2)169
N2—H2A···N30.862.222.650 (2)111
N4—H4A···S2ii0.862.633.475 (1)169
N5—H5A···N60.862.252.666 (2)110
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+1, −y+2, −z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···S1i0.862.553.399 (2)169
N2—H2A···N30.862.222.650 (2)111
N4—H4A···S2ii0.862.633.475 (1)169
N5—H5A···N60.862.252.666 (2)110
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+1, −y+2, −z.
Acknowledgements top

DG thanks the Council of Scientific and Industrial Research (CSIR), India, for a Senior Research Fellowship. Financial support from the University Grants Commission (UGC–SAP) and the Department of Science & Technology (DST–FIST), Government of India, is acknowledged by DV for providing facilities to the department.

references
References top

Bruker (2001). SMART (Version. 5.625/NT/2000) and SAINT (Version 6.28a). Bruker AXS Inc., Madison, Wisconsin, USA.

Gayathri, D., Velmurugan, D., Ravikumar, K., Devaraj, S. & Kandaswamy, M. (2007). Acta Cryst. E63, o2226–o2227.

Lee, D. H., Im, J. H., Son, S. U., Chung, Y. K. & Hong, J.-I. (2003). J. Am. Chem. Soc. 125, 7752–7753.

Lee, C. H., Lee, J. S., Na, H. K., Yoon, D. W., Miyaji, H., Cho, W. S. & Sessler, J. L. (2005). J. Org. Chem. 70, 2067–2074.

Nardelli, M. (1995). J. Appl. Cryst. 28, 659–?.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13.

Yoon, J., Kim, S. K., Sing, N. J., Lee, J. W., Yang, Y. J., Chellappan, K. & Kim, K. S. (2004). J. Org. Chem. 69, 581–583.