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The mol­ecule in the title compound, C11H13N3O3S, adopts a transcis configuration with respect to the positions of the butanoyl and 4-nitro­phenyl groups relative to the S atom across their respective C—N bonds. In the crystal structure, mol­ecules are linked into two-dimensional networks by N—H...S and C—H...O inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807038433/bi2219sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807038433/bi2219Isup2.hkl
Contains datablock I

CCDC reference: 660270

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.043
  • wR factor = 0.128
  • Data-to-parameter ratio = 15.5

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C11 H13 N3 O3 S
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

The title compound is similar to the previously reported compound N-(4-methylbenzoyl)-N'-(4-nitrophenyl)thiourea (Yusof et al., 2006), except that the 4-methylbenzoyl group is replaced by a butanoyl group. The bond lengths and angles are comparable to those in that compound and to other thiourea derivatives (Yusof et al., 2007a,b). The central thiourea fragment (S1/C5/N1/N2) and phenyl ring (C6–C7) are essentially planar with maximum deviation of 0.013 (1) Å for atom N1, and the dihedral angle between them is 5.27 (8)°. An intramolecular hydrogen bond, N2—H2A···O1, forms a pseudo-six-membered ring (O1···H2A/N2/C5/N1/C4), and a relatively short intramolecular C—H···S contact is also observed (H11A···S1 = 2.56 Å, C11···S1 = 3.222 (2) Å, C11—H11A···S1 = 128 °). In the crystal structure, the molecules are linked into two-dimensional networks parallel to the bc planes via intermolecular N—H···S and C—H···O interactions (Fig. 2 & Table 1).

Related literature top

For some related structures, see: Yusof et al. (2006, 2007a,b).

Experimental top

To a stirring acetone solution (75 ml) of butyrylchloride (2.0 g, 19 mmol) and ammoniumthiocyanate (1.43 g, 19 mmol), 4-nitroaniline (2.59 g, 19 mmol) in 45 ml of acetone was added dropwise. The solution mixture was refluxed for 1 h. The resulting solution was poured into a beaker containing some ice blocks. The white precipitate was filtered off and washed with distilled water and cold ethanol then dried under vacuum. Good quality crystals were obtained by recrystallization from DMSO. Yield 74% (2.03 g).

Refinement top

All H atoms were visible in difference Fourier maps, but were placed geometrically at ideal positions then allowed to ride on their parent C or N atoms with C—H = 0.93–0.97 Å and N—H = 0.86 Å, and with Uiso(H)= 1.2(C/N) or 1.5Ueq(methyl C).

Structure description top

The title compound is similar to the previously reported compound N-(4-methylbenzoyl)-N'-(4-nitrophenyl)thiourea (Yusof et al., 2006), except that the 4-methylbenzoyl group is replaced by a butanoyl group. The bond lengths and angles are comparable to those in that compound and to other thiourea derivatives (Yusof et al., 2007a,b). The central thiourea fragment (S1/C5/N1/N2) and phenyl ring (C6–C7) are essentially planar with maximum deviation of 0.013 (1) Å for atom N1, and the dihedral angle between them is 5.27 (8)°. An intramolecular hydrogen bond, N2—H2A···O1, forms a pseudo-six-membered ring (O1···H2A/N2/C5/N1/C4), and a relatively short intramolecular C—H···S contact is also observed (H11A···S1 = 2.56 Å, C11···S1 = 3.222 (2) Å, C11—H11A···S1 = 128 °). In the crystal structure, the molecules are linked into two-dimensional networks parallel to the bc planes via intermolecular N—H···S and C—H···O interactions (Fig. 2 & Table 1).

For some related structures, see: Yusof et al. (2006, 2007a,b).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound showing displacement ellipsoids at the 50% probability level for non-H atoms. The dashed line indicates an N—H···O hydrogen bond.
[Figure 2] Fig. 2. Partial packing diagram, viewed down the a-axis. The dashed lines denote N—H···S and C—H···O interactions.
N-Butanoyl-N'-(4-nitrophenyl)thiourea top
Crystal data top
C11H13N3O3SF(000) = 560
Mr = 267.30Dx = 1.367 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 894 reflections
a = 4.9002 (12) Åθ = 1.9–26°
b = 12.385 (3) ŵ = 0.25 mm1
c = 21.774 (5) ÅT = 293 K
β = 100.727 (6)°Block, light yellow
V = 1298.3 (5) Å30.51 × 0.50 × 0.46 mm
Z = 4
Data collection top
Bruker SMART APEX CCD
diffractometer
2540 independent reflections
Radiation source: fine-focus sealed tube1933 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.018
ω scansθmax = 26.0°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 63
Tmin = 0.882, Tmax = 0.892k = 1514
7048 measured reflectionsl = 2626
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)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0696P)2 + 0.2521P]
where P = (Fo2 + 2Fc2)/3
2540 reflections(Δ/σ)max < 0.001
164 parametersΔρmax = 0.23 e Å3
0 restraintsΔρmin = 0.16 e Å3
Crystal data top
C11H13N3O3SV = 1298.3 (5) Å3
Mr = 267.30Z = 4
Monoclinic, P21/cMo Kα radiation
a = 4.9002 (12) ŵ = 0.25 mm1
b = 12.385 (3) ÅT = 293 K
c = 21.774 (5) Å0.51 × 0.50 × 0.46 mm
β = 100.727 (6)°
Data collection top
Bruker SMART APEX CCD
diffractometer
2540 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
1933 reflections with I > 2σ(I)
Tmin = 0.882, Tmax = 0.892Rint = 0.018
7048 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0430 restraints
wR(F2) = 0.128H-atom parameters constrained
S = 1.03Δρmax = 0.23 e Å3
2540 reflectionsΔρmin = 0.16 e Å3
164 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
S10.82531 (12)0.85936 (4)0.46315 (2)0.0606 (2)
O10.5256 (3)1.15131 (11)0.36784 (8)0.0678 (4)
O20.0653 (4)0.61661 (16)0.22970 (9)0.0912 (6)
O30.1567 (5)0.50150 (15)0.27592 (10)0.1057 (7)
N10.7852 (3)1.06019 (12)0.42783 (7)0.0538 (4)
H1A0.90451.06980.45170.065*
N20.5553 (3)0.93999 (12)0.37607 (7)0.0535 (4)
H2A0.50990.99940.36020.064*
N30.0939 (4)0.59385 (17)0.26469 (9)0.0716 (5)
C10.8042 (7)1.4546 (2)0.43218 (16)0.1014 (10)
H1B0.69111.51660.42820.152*
H1C0.98401.46390.40630.152*
H1D0.82421.44690.47500.152*
C20.6687 (6)1.35530 (18)0.41193 (14)0.0844 (8)
H2B0.47911.35120.43470.101*
H2C0.66221.36130.36780.101*
C30.8166 (5)1.25460 (17)0.42254 (12)0.0687 (6)
H3A0.82291.24950.46670.082*
H3B1.00661.25990.40010.082*
C40.6927 (4)1.15281 (16)0.40304 (10)0.0557 (5)
C50.7122 (4)0.95391 (15)0.41966 (8)0.0478 (4)
C60.4504 (4)0.84770 (14)0.35126 (9)0.0482 (4)
C70.2850 (4)0.86884 (16)0.30707 (9)0.0558 (5)
H7A0.25360.94000.29660.067*
C80.1682 (4)0.78694 (17)0.27893 (9)0.0598 (5)
H8A0.05640.80150.24980.072*
C90.2196 (4)0.68234 (17)0.29470 (9)0.0567 (5)
C100.3827 (5)0.65870 (16)0.33746 (11)0.0635 (6)
H10A0.41460.58730.34720.076*
C110.4999 (4)0.74187 (16)0.36612 (10)0.0611 (5)
H11A0.61140.72670.39520.073*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0715 (4)0.0573 (3)0.0613 (4)0.0000 (2)0.0338 (3)0.0062 (2)
O10.0797 (11)0.0556 (8)0.0808 (10)0.0014 (7)0.0480 (9)0.0016 (7)
O20.0923 (13)0.0943 (13)0.0985 (13)0.0146 (10)0.0478 (11)0.0184 (10)
O30.1409 (18)0.0634 (12)0.1246 (16)0.0070 (11)0.0552 (14)0.0201 (10)
N10.0552 (10)0.0537 (9)0.0599 (10)0.0003 (7)0.0298 (8)0.0014 (7)
N20.0584 (10)0.0490 (9)0.0599 (9)0.0002 (7)0.0285 (8)0.0028 (7)
N30.0749 (13)0.0690 (13)0.0720 (12)0.0105 (10)0.0166 (10)0.0164 (10)
C10.127 (3)0.0594 (15)0.131 (2)0.0039 (15)0.058 (2)0.0052 (15)
C20.105 (2)0.0579 (14)0.105 (2)0.0031 (12)0.0562 (17)0.0037 (12)
C30.0747 (15)0.0552 (12)0.0860 (16)0.0019 (10)0.0399 (12)0.0003 (10)
C40.0574 (12)0.0538 (11)0.0607 (12)0.0012 (9)0.0236 (10)0.0002 (8)
C50.0432 (10)0.0551 (11)0.0473 (10)0.0004 (8)0.0143 (8)0.0000 (8)
C60.0458 (10)0.0505 (10)0.0510 (10)0.0013 (8)0.0161 (8)0.0015 (8)
C70.0615 (13)0.0548 (11)0.0571 (11)0.0016 (9)0.0267 (10)0.0043 (9)
C80.0606 (12)0.0674 (13)0.0564 (11)0.0036 (10)0.0241 (10)0.0014 (9)
C90.0532 (12)0.0616 (12)0.0567 (11)0.0073 (9)0.0140 (9)0.0097 (9)
C100.0697 (14)0.0464 (11)0.0781 (15)0.0015 (9)0.0231 (12)0.0017 (9)
C110.0659 (13)0.0543 (11)0.0716 (13)0.0034 (9)0.0346 (11)0.0003 (10)
Geometric parameters (Å, º) top
S1—C51.6646 (19)C2—H2B0.970
O1—C41.221 (2)C2—H2C0.970
O2—N31.221 (3)C3—C41.495 (3)
O3—N31.221 (3)C3—H3A0.970
N1—C41.380 (2)C3—H3B0.970
N1—C51.384 (2)C6—C111.382 (3)
N1—H1A0.860C6—C71.393 (3)
N2—C51.339 (2)C7—C81.365 (3)
N2—C61.402 (2)C7—H7A0.930
N2—H2A0.860C8—C91.375 (3)
N3—C91.469 (3)C8—H8A0.930
C1—C21.503 (3)C9—C101.367 (3)
C1—H1B0.960C10—C111.383 (3)
C1—H1C0.960C10—H10A0.930
C1—H1D0.960C11—H11A0.930
C2—C31.482 (3)
C4—N1—C5128.95 (16)H3A—C3—H3B107.5
C4—N1—H1A115.6O1—C4—N1122.71 (17)
C5—N1—H1A115.5O1—C4—C3123.12 (17)
C5—N2—C6132.70 (16)N1—C4—C3114.17 (17)
C5—N2—H2A113.6N2—C5—N1114.19 (16)
C6—N2—H2A113.7N2—C5—S1127.48 (14)
O2—N3—O3123.7 (2)N1—C5—S1118.32 (13)
O2—N3—C9118.4 (2)C11—C6—C7119.32 (17)
O3—N3—C9117.9 (2)C11—C6—N2126.15 (17)
C2—C1—H1B109.5C7—C6—N2114.52 (16)
C2—C1—H1C109.5C8—C7—C6121.12 (18)
H1B—C1—H1C109.5C8—C7—H7A119.4
C2—C1—H1D109.5C6—C7—H7A119.4
H1B—C1—H1D109.5C7—C8—C9118.45 (19)
H1C—C1—H1D109.5C7—C8—H8A120.8
C3—C2—C1112.8 (2)C9—C8—H8A120.8
C3—C2—H2B109.0C10—C9—C8121.95 (18)
C1—C2—H2B109.0C10—C9—N3119.3 (2)
C3—C2—H2C109.0C8—C9—N3118.7 (2)
C1—C2—H2C109.0C9—C10—C11119.49 (19)
H2B—C2—H2C107.8C9—C10—H10A120.3
C2—C3—C4115.40 (18)C11—C10—H10A120.3
C2—C3—H3A108.4C6—C11—C10119.66 (18)
C4—C3—H3A108.4C6—C11—H11A120.2
C2—C3—H3B108.4C10—C11—H11A120.2
C4—C3—H3B108.4
C1—C2—C3—C4179.7 (2)C6—C7—C8—C90.6 (3)
C5—N1—C4—O10.9 (4)C7—C8—C9—C100.1 (3)
C5—N1—C4—C3179.61 (19)C7—C8—C9—N3179.85 (18)
C2—C3—C4—O116.9 (4)O2—N3—C9—C10175.4 (2)
C2—C3—C4—N1163.6 (2)O3—N3—C9—C105.2 (3)
C6—N2—C5—N1176.16 (18)O2—N3—C9—C84.4 (3)
C6—N2—C5—S13.5 (3)O3—N3—C9—C8175.1 (2)
C4—N1—C5—N28.5 (3)C8—C9—C10—C110.2 (3)
C4—N1—C5—S1171.81 (16)N3—C9—C10—C11179.57 (19)
C5—N2—C6—C112.9 (3)C7—C6—C11—C100.6 (3)
C5—N2—C6—C7178.0 (2)N2—C6—C11—C10179.7 (2)
C11—C6—C7—C80.9 (3)C9—C10—C11—C60.1 (3)
N2—C6—C7—C8179.92 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O10.861.892.629 (2)143
N1—H1A···S1i0.862.623.4579 (18)164
C7—H7A···O2ii0.932.483.397 (3)168
Symmetry codes: (i) x+2, y2, z1; (ii) x, y1/2, z1/2.

Experimental details

Crystal data
Chemical formulaC11H13N3O3S
Mr267.30
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)4.9002 (12), 12.385 (3), 21.774 (5)
β (°) 100.727 (6)
V3)1298.3 (5)
Z4
Radiation typeMo Kα
µ (mm1)0.25
Crystal size (mm)0.51 × 0.50 × 0.46
Data collection
DiffractometerBruker SMART APEX CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2000)
Tmin, Tmax0.882, 0.892
No. of measured, independent and
observed [I > 2σ(I)] reflections
7048, 2540, 1933
Rint0.018
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.128, 1.03
No. of reflections2540
No. of parameters164
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.23, 0.16

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O10.861.892.629 (2)143
N1—H1A···S1i0.862.623.4579 (18)164
C7—H7A···O2ii0.932.483.397 (3)168
Symmetry codes: (i) x+2, y2, z1; (ii) x, y1/2, z1/2.
 

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