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Acta Crystallogr Sect E Struct Rep Online. 2009 October 1; 65(Pt 10): o2447.
Published online 2009 September 12. doi:  10.1107/S1600536809035880
PMCID: PMC2970362

1-[2-(2,4-Dinitro­benzyl­ideneamino)phen­yl]-3-phenyl­thio­urea

Abstract

In the title compound, C20H15N5O4S, the central benzene ring makes dihedral angles of 59.5 (1) and 51.7 (1)°, respectively, with the terminal phenyl and benzene rings. The mol­ecular structure exhibits weak intra­molecular N—H(...)N and C—H(...)S inter­actions. In the crystal structure, mol­ecules are linked by weak inter­molecular N—H(...)S and C—H(...)O inter­actions, forming a chain along [1An external file that holds a picture, illustration, etc.
Object name is e-65-o2447-efi1.jpg1].

Related literature

For the biological activity of thio­ureas, see: Huebner et al. (1953 [triangle]); Madan & Taneja (1991 [triangle]); Manjula et al. (2009 [triangle]). For related structures, see: Gayathri et al. (2007 [triangle], 2008 [triangle]). For graph-set notation, see: Bernstein et al. (1995 [triangle]).

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Object name is e-65-o2447-scheme1.jpg

Experimental

Crystal data

  • C20H15N5O4S
  • M r = 421.43
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2447-efi2.jpg
  • a = 8.362 (5) Å
  • b = 18.767 (3) Å
  • c = 12.379 (4) Å
  • β = 94.827 (5)°
  • V = 1935.7 (14) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.21 mm−1
  • T = 295 K
  • 0.20 × 0.16 × 0.16 mm

Data collection

  • Bruker Kappa APEXII diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.960, T max = 0.968
  • 28336 measured reflections
  • 6878 independent reflections
  • 4509 reflections with I > 2σ(I)
  • R int = 0.028

Refinement

  • R[F 2 > 2σ(F 2)] = 0.046
  • wR(F 2) = 0.137
  • S = 1.02
  • 6878 reflections
  • 271 parameters
  • H-atom parameters constrained
  • Δρmax = 0.25 e Å−3
  • Δρmin = −0.37 e Å−3

Data collection: APEX2 (Bruker, 2004 [triangle]); cell refinement: SAINT (Bruker, 2004 [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: PLATON (Spek, 2009 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809035880/is2457sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809035880/is2457Isup2.hkl

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

Acknowledgments

The authors wish to acknowledge IIT, Madras for the data collection.

supplementary crystallographic information

Comment

Thioureas are known to exhibit antiviral, antibacterial, anticancer (Madan & Taneja, 1991; Manjula et al., 2009), antifungal, antitubercular, antithyroidal, herbicidal and insecticidal (Huebner et al., 1953) activities.

The geometric parameters in (I), (Fig. 1) agree with the reported values of similar structures (Gayathri et al., 2007, 2008). The benzene ring C1—C6 makes the dihedral angle of 59.5 (1)° with the phenyl ring C15—C20 and 51.7 (1)° with the dinitrobenzene ring C8—C13.

The molecular structure of (I) exhibits weak intramolecular N—H···N, C—H···S and C—H···O interactions and the crystal structure is stabilized by weak intermolecular N—H···S and C—H···O interactions (Table 1 and Fig. 2). The intermolecular N5—H5A···S1 interaction generates an eight-membered ring, with graph-set motif R22(8) and the C12—H12···O3 interaction generates a ten-membered ring, with graph-set motif R22(10) (Bernstein, 1995).

Experimental

To the solution of 1-(2-aminophenyl)-3-phenylthiourea (0.3 g, 1.2 mmol) in methanol (25 ml), 2,4-dinitrobenzaldehyde (0.36 g, 1.2 mmol) in methanol (25 ml) was added under stirring. The resulting mixture was refluxed 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 chloroform.

Refinement

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

Figures

Fig. 1.
The molecular structure of (I), with atom labels and 30% probability displacement ellipsoids for non-H atoms.
Fig. 2.
The packing of (I), viewed down the a axis. Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted.

Crystal data

C20H15N5O4SF(000) = 872
Mr = 421.43Dx = 1.446 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9702 reflections
a = 8.362 (5) Åθ = 2.2–32.3°
b = 18.767 (3) ŵ = 0.21 mm1
c = 12.379 (4) ÅT = 295 K
β = 94.827 (5)°Prism, orange
V = 1935.7 (14) Å30.20 × 0.16 × 0.16 mm
Z = 4

Data collection

Bruker Kappa APEXII diffractometer6878 independent reflections
Radiation source: fine-focus sealed tube4509 reflections with I > 2σ(I)
graphiteRint = 0.028
ω and [var phi] scansθmax = 32.3°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −12→12
Tmin = 0.960, Tmax = 0.968k = −28→26
28336 measured reflectionsl = −9→18

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.137H-atom parameters constrained
S = 1.02w = 1/[σ2(Fo2) + (0.0628P)2 + 0.3472P] where P = (Fo2 + 2Fc2)/3
6878 reflections(Δ/σ)max < 0.001
271 parametersΔρmax = 0.25 e Å3
0 restraintsΔρmin = −0.37 e Å3

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

xyzUiso*/Ueq
C10.62398 (16)0.29698 (7)0.34283 (10)0.0381 (3)
C20.65955 (15)0.23913 (7)0.41328 (9)0.0360 (3)
C30.76661 (18)0.24941 (8)0.50420 (11)0.0448 (3)
H30.78600.21270.55410.054*
C40.84381 (19)0.31360 (9)0.52044 (12)0.0511 (4)
H40.91490.32000.58160.061*
C50.8174 (2)0.36867 (9)0.44751 (13)0.0560 (4)
H50.87400.41110.45760.067*
C60.70627 (19)0.36049 (8)0.35919 (12)0.0496 (4)
H60.68680.39790.31060.060*
C70.42126 (16)0.33645 (8)0.21914 (10)0.0412 (3)
H70.43210.38090.25220.049*
C80.30541 (16)0.32650 (7)0.12401 (10)0.0381 (3)
C90.32496 (18)0.26958 (8)0.05491 (11)0.0459 (3)
H90.40400.23590.07390.055*
C100.23061 (19)0.26145 (9)−0.04113 (11)0.0478 (3)
H100.24410.2225−0.08590.057*
C110.11616 (16)0.31229 (8)−0.06909 (10)0.0425 (3)
C120.08777 (17)0.36881 (8)−0.00335 (11)0.0424 (3)
H120.00870.4023−0.02340.051*
C130.18123 (16)0.37421 (8)0.09399 (10)0.0393 (3)
C140.57689 (16)0.11081 (7)0.42739 (10)0.0387 (3)
C150.41735 (19)0.06746 (7)0.26115 (11)0.0435 (3)
C160.2548 (2)0.05512 (8)0.24467 (12)0.0471 (3)
H160.19550.04570.30340.057*
C170.1798 (2)0.05672 (10)0.14094 (14)0.0606 (4)
H170.07000.04820.12980.073*
C180.2668 (3)0.07077 (10)0.05446 (13)0.0687 (5)
H180.21610.0721−0.01530.082*
C190.4278 (3)0.08286 (11)0.07051 (14)0.0703 (5)
H190.48620.09230.01140.084*
C200.5058 (2)0.08133 (10)0.17423 (13)0.0599 (4)
H200.61570.08950.18490.072*
N10.01932 (16)0.30558 (9)−0.17349 (10)0.0534 (3)
N20.14010 (17)0.43172 (8)0.16707 (11)0.0542 (3)
N30.50634 (14)0.28461 (6)0.25608 (9)0.0406 (3)
N40.58017 (14)0.17574 (6)0.38222 (8)0.0409 (3)
H4A0.52160.17910.32190.049*
N50.49272 (17)0.06127 (7)0.36821 (10)0.0529 (3)
H5A0.48320.02060.39900.064*
O10.0455 (2)0.25501 (10)−0.23077 (11)0.0917 (5)
O2−0.08088 (15)0.35115 (8)−0.19739 (9)0.0652 (3)
O30.0704 (2)0.48301 (8)0.12851 (13)0.0930 (5)
O40.1705 (2)0.42321 (9)0.26429 (11)0.0902 (5)
S10.66368 (5)0.08789 (2)0.55035 (3)0.04838 (12)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0389 (7)0.0402 (7)0.0341 (5)0.0022 (5)−0.0038 (5)0.0060 (5)
C20.0366 (7)0.0377 (7)0.0330 (5)0.0040 (5)−0.0017 (5)0.0047 (5)
C30.0487 (8)0.0449 (8)0.0384 (6)0.0049 (6)−0.0100 (5)0.0062 (5)
C40.0529 (9)0.0506 (9)0.0465 (7)0.0005 (7)−0.0159 (6)−0.0013 (6)
C50.0595 (10)0.0439 (8)0.0609 (9)−0.0082 (7)−0.0171 (7)0.0021 (7)
C60.0544 (9)0.0403 (8)0.0516 (8)−0.0045 (6)−0.0108 (6)0.0107 (6)
C70.0429 (7)0.0426 (7)0.0368 (6)0.0018 (6)−0.0041 (5)0.0065 (5)
C80.0371 (7)0.0428 (7)0.0335 (5)0.0017 (5)−0.0012 (5)0.0091 (5)
C90.0442 (8)0.0509 (8)0.0416 (6)0.0108 (6)−0.0018 (5)0.0056 (6)
C100.0498 (8)0.0550 (9)0.0381 (6)0.0062 (7)0.0015 (6)−0.0022 (6)
C110.0374 (7)0.0572 (9)0.0322 (5)−0.0021 (6)−0.0015 (5)0.0077 (5)
C120.0375 (7)0.0482 (8)0.0405 (6)0.0042 (6)−0.0030 (5)0.0106 (5)
C130.0403 (7)0.0408 (7)0.0364 (6)0.0024 (6)0.0002 (5)0.0062 (5)
C140.0401 (7)0.0392 (7)0.0364 (6)0.0017 (5)−0.0001 (5)0.0072 (5)
C150.0586 (9)0.0340 (7)0.0369 (6)−0.0010 (6)−0.0032 (6)0.0032 (5)
C160.0558 (9)0.0397 (7)0.0455 (7)0.0040 (7)0.0019 (6)−0.0005 (6)
C170.0665 (11)0.0515 (10)0.0602 (9)0.0048 (8)−0.0163 (8)−0.0025 (7)
C180.1052 (16)0.0567 (11)0.0405 (7)0.0006 (10)−0.0150 (8)−0.0024 (7)
C190.1034 (17)0.0702 (12)0.0388 (7)−0.0056 (11)0.0143 (9)0.0021 (7)
C200.0657 (11)0.0657 (11)0.0489 (8)−0.0085 (9)0.0079 (7)0.0050 (7)
N10.0498 (7)0.0732 (10)0.0357 (5)−0.0006 (7)−0.0040 (5)0.0038 (6)
N20.0549 (8)0.0525 (8)0.0531 (7)0.0126 (6)−0.0072 (6)−0.0041 (6)
N30.0413 (6)0.0429 (6)0.0360 (5)−0.0013 (5)−0.0064 (4)0.0103 (4)
N40.0464 (6)0.0384 (6)0.0358 (5)−0.0013 (5)−0.0096 (4)0.0074 (4)
N50.0704 (9)0.0438 (7)0.0420 (6)−0.0131 (6)−0.0106 (6)0.0141 (5)
O10.1080 (12)0.1083 (13)0.0534 (7)0.0283 (10)−0.0248 (7)−0.0255 (8)
O20.0583 (7)0.0850 (9)0.0490 (6)0.0074 (6)−0.0157 (5)0.0116 (6)
O30.1231 (13)0.0625 (9)0.0886 (10)0.0423 (9)−0.0200 (9)−0.0069 (7)
O40.1129 (13)0.1065 (12)0.0489 (7)0.0467 (10)−0.0073 (7)−0.0162 (7)
S10.0547 (2)0.0481 (2)0.04016 (17)−0.00134 (16)−0.00860 (14)0.01530 (14)

Geometric parameters (Å, °)

C1—C61.383 (2)C12—H120.9300
C1—C21.4085 (17)C13—N21.468 (2)
C1—N31.4132 (16)C14—N41.3419 (17)
C2—C31.3914 (18)C14—N51.3452 (19)
C2—N41.4003 (17)C14—S11.6860 (13)
C3—C41.374 (2)C15—C161.377 (2)
C3—H30.9300C15—C201.381 (2)
C4—C51.378 (2)C15—N51.4236 (17)
C4—H40.9300C16—C171.381 (2)
C5—C61.383 (2)C16—H160.9300
C5—H50.9300C17—C181.370 (3)
C6—H60.9300C17—H170.9300
C7—N31.2678 (17)C18—C191.363 (3)
C7—C81.4725 (18)C18—H180.9300
C7—H70.9300C19—C201.391 (2)
C8—C91.387 (2)C19—H190.9300
C8—C131.3975 (19)C20—H200.9300
C9—C101.379 (2)N1—O11.215 (2)
C9—H90.9300N1—O21.2162 (19)
C10—C111.375 (2)N2—O31.2031 (18)
C10—H100.9300N2—O41.2194 (18)
C11—C121.370 (2)N4—H4A0.8600
C11—N11.4716 (17)N5—H5A0.8600
C12—C131.3837 (18)
C6—C1—C2119.82 (12)C12—C13—N2116.50 (12)
C6—C1—N3123.98 (12)C8—C13—N2120.97 (12)
C2—C1—N3116.18 (12)N4—C14—N5115.39 (11)
C3—C2—N4126.71 (12)N4—C14—S1125.83 (11)
C3—C2—C1118.81 (13)N5—C14—S1118.76 (10)
N4—C2—C1114.48 (11)C16—C15—C20120.20 (14)
C4—C3—C2120.16 (13)C16—C15—N5118.58 (13)
C4—C3—H3119.9C20—C15—N5121.10 (15)
C2—C3—H3119.9C15—C16—C17119.97 (15)
C3—C4—C5120.97 (13)C15—C16—H16120.0
C3—C4—H4119.5C17—C16—H16120.0
C5—C4—H4119.5C18—C17—C16120.07 (18)
C4—C5—C6119.67 (15)C18—C17—H17120.0
C4—C5—H5120.2C16—C17—H17120.0
C6—C5—H5120.2C19—C18—C17120.09 (15)
C5—C6—C1120.30 (13)C19—C18—H18120.0
C5—C6—H6119.9C17—C18—H18120.0
C1—C6—H6119.9C18—C19—C20120.80 (17)
N3—C7—C8120.17 (13)C18—C19—H19119.6
N3—C7—H7119.9C20—C19—H19119.6
C8—C7—H7119.9C15—C20—C19118.87 (18)
C9—C8—C13116.94 (12)C15—C20—H20120.6
C9—C8—C7119.16 (12)C19—C20—H20120.6
C13—C8—C7123.75 (13)O1—N1—O2124.14 (13)
C10—C9—C8121.91 (13)O1—N1—C11117.79 (14)
C10—C9—H9119.0O2—N1—C11118.06 (14)
C8—C9—H9119.0O3—N2—O4123.37 (15)
C11—C10—C9118.42 (14)O3—N2—C13118.34 (13)
C11—C10—H10120.8O4—N2—C13118.15 (13)
C9—C10—H10120.8C7—N3—C1118.79 (12)
C12—C11—C10122.65 (12)C14—N4—C2133.07 (11)
C12—C11—N1118.55 (13)C14—N4—H4A113.5
C10—C11—N1118.80 (14)C2—N4—H4A113.5
C11—C12—C13117.43 (13)C14—N5—C15128.38 (12)
C11—C12—H12121.3C14—N5—H5A115.8
C13—C12—H12121.3C15—N5—H5A115.8
C12—C13—C8122.50 (13)
C6—C1—C2—C36.0 (2)N5—C15—C16—C17−176.32 (14)
N3—C1—C2—C3−175.84 (12)C15—C16—C17—C18−0.2 (2)
C6—C1—C2—N4−173.89 (14)C16—C17—C18—C190.3 (3)
N3—C1—C2—N44.25 (18)C17—C18—C19—C20−0.2 (3)
N4—C2—C3—C4175.60 (15)C16—C15—C20—C190.3 (3)
C1—C2—C3—C4−4.3 (2)N5—C15—C20—C19176.38 (16)
C2—C3—C4—C5−0.2 (3)C18—C19—C20—C15−0.1 (3)
C3—C4—C5—C63.0 (3)C12—C11—N1—O1−179.74 (16)
C4—C5—C6—C1−1.2 (3)C10—C11—N1—O1−0.1 (2)
C2—C1—C6—C5−3.3 (2)C12—C11—N1—O20.8 (2)
N3—C1—C6—C5178.69 (15)C10—C11—N1—O2−179.62 (15)
N3—C7—C8—C9−20.9 (2)C12—C13—N2—O3−24.3 (2)
N3—C7—C8—C13163.79 (13)C8—C13—N2—O3157.70 (17)
C13—C8—C9—C102.3 (2)C12—C13—N2—O4151.72 (17)
C7—C8—C9—C10−173.30 (14)C8—C13—N2—O4−26.3 (2)
C8—C9—C10—C111.1 (2)C8—C7—N3—C1175.78 (12)
C9—C10—C11—C12−2.8 (2)C6—C1—N3—C7−31.3 (2)
C9—C10—C11—N1177.57 (13)C2—C1—N3—C7150.61 (13)
C10—C11—C12—C130.9 (2)N5—C14—N4—C2−175.70 (14)
N1—C11—C12—C13−179.52 (12)S1—C14—N4—C25.9 (2)
C11—C12—C13—C82.9 (2)C3—C2—N4—C142.5 (2)
C11—C12—C13—N2−175.14 (13)C1—C2—N4—C14−177.57 (14)
C9—C8—C13—C12−4.4 (2)N4—C14—N5—C155.2 (2)
C7—C8—C13—C12171.00 (13)S1—C14—N5—C15−176.34 (13)
C9—C8—C13—N2173.51 (13)C16—C15—N5—C14−121.98 (17)
C7—C8—C13—N2−11.1 (2)C20—C15—N5—C1461.8 (2)
C20—C15—C16—C17−0.1 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N4—H4A···N30.862.142.614 (2)114
C3—H3···S10.932.553.215 (2)128
C7—H7···O40.932.342.749 (3)106
N4—H4A···N30.862.142.614 (2)114
N5—H5A···S1i0.862.493.284 (2)155
C12—H12···O3ii0.932.573.397 (3)148

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS2457).

References

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