Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807037762/hg2267sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807037762/hg2267Isup2.hkl |
CCDC reference: 660211
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.045
- wR factor = 0.115
- Data-to-parameter ratio = 18.1
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT431_ALERT_2_B Short Inter HL..A Contact Cl1 .. O1 .. 2.96 Ang.
Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.30 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.85 Ratio
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 1 ALERT level B = Potentially serious problem 2 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 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
To a stirring acetone solution (75 ml) of decanoyl chloride (2.0 g, 10 mmol) and ammoniumthiocyanate (0.80 g, 10 mmol), 3,4-dichloroaniline (1.70 g, 10 mmol) in 40 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 before dried under vacuum. Good quality crystals were obtained by recrystallization from THF. Yield 75% (2.31 g).
After their location in the difference map, all H-atoms were fixed geometrically at ideal positions and allowed to ride on the parent C or N atoms with C—H = 0.93–0.97 Å and N—H = 0.86 Å with Uiso(H)= 1.2 (CH2 and NH) or 1.5Ueq(C)(CH3).
Thiourea derivatives receive considerable attention because of their potential applications in materials science (Wei et al., 2004) and their biological activities (Baruah et al., 2002). The title compound, (I), is similar to N-(3,4-Dichlorophenyl)-N'-(3-nitrobenzoyl)thiourea, (Yusof et al., 2006), except that the 3-nitrobenzoyl group is replaced by a decanoyl group (Fig.1). The molecule maintains its trans-cis configuration with respect to the position of the decanoyl and 3,4-dichlorophenyl groups relative to the thiono S1 atom across their C—N bonds, respectively. The bond lengths and angles are in normal ranges (Allen et al., 1987) and comparable with other thiourea derivatives (Yusof, Ramlee et al. (2007); Yusof, Yaakob et al. (2007). The thiourea-3,4-dichlorophenyl (S1/N1/N2/C11—C17/Cl1/Cl2) fragment are essentially planar with a maximum deviation of 0.039 (2) Å for atom C10 from the least-squares plane.
There are two intramolecular hydrogen bonds, N2—H2···O1 and C17—H17···S1 (Table 2), forming two pseudo-six-membered rings (O1···H2—N2—C11—N1—C10—O1 and S1···H17—C17—C12—N2—C11—S1). In the crystal structure, the molecules are linked by intermolecular interactions, N—H···S and C—H···S (symmetry codes as in Table 2) forming dimers parallel to b axis (Fig.2).
For related crystal structures of the title compound, see: Yusof, Ramlee et al. (2007); Yusof, Yaakob et al. (2007). For details of potential applications in materials and biological activities, see: Wei et al. (2004); Baruah et al. (2002).
For related literature, see: Allen et al. (1987); Yusof et al. (2006).
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).
C17H24Cl2N2OS | Z = 2 |
Mr = 375.34 | F(000) = 396 |
Triclinic, P1 | Dx = 1.286 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 4.7368 (13) Å | Cell parameters from 797 reflections |
b = 11.295 (3) Å | θ = 1.8–25.9° |
c = 18.324 (5) Å | µ = 0.45 mm−1 |
α = 88.289 (5)° | T = 293 K |
β = 83.774 (5)° | Slab, colourless |
γ = 84.268 (4)° | 0.46 × 0.41 × 0.09 mm |
V = 969.5 (5) Å3 |
Bruker SMART APEX CCD area-detector diffractometer | 3778 independent reflections |
Radiation source: fine-focus sealed tube | 2856 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
Detector resolution: 83.66 pixels mm-1 | θmax = 26.0°, θmin = 1.8° |
ω scans | h = −5→5 |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | k = −13→13 |
Tmin = 0.821, Tmax = 0.961 | l = −22→22 |
10011 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.115 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0538P)2 + 0.1967P] where P = (Fo2 + 2Fc2)/3 |
3778 reflections | (Δ/σ)max < 0.001 |
209 parameters | Δρmax = 0.26 e Å−3 |
0 restraints | Δρmin = −0.15 e Å−3 |
C17H24Cl2N2OS | γ = 84.268 (4)° |
Mr = 375.34 | V = 969.5 (5) Å3 |
Triclinic, P1 | Z = 2 |
a = 4.7368 (13) Å | Mo Kα radiation |
b = 11.295 (3) Å | µ = 0.45 mm−1 |
c = 18.324 (5) Å | T = 293 K |
α = 88.289 (5)° | 0.46 × 0.41 × 0.09 mm |
β = 83.774 (5)° |
Bruker SMART APEX CCD area-detector diffractometer | 3778 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | 2856 reflections with I > 2σ(I) |
Tmin = 0.821, Tmax = 0.961 | Rint = 0.027 |
10011 measured reflections |
R[F2 > 2σ(F2)] = 0.045 | 0 restraints |
wR(F2) = 0.115 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.26 e Å−3 |
3778 reflections | Δρmin = −0.15 e Å−3 |
209 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.01781 (13) | −0.07409 (5) | 0.37362 (4) | 0.0680 (2) | |
Cl2 | 0.2794 (2) | −0.02429 (7) | 0.21084 (4) | 0.0968 (3) | |
S1 | 0.91305 (13) | 0.40736 (5) | 0.40393 (3) | 0.05798 (19) | |
O1 | 0.3719 (3) | 0.26352 (14) | 0.59943 (8) | 0.0627 (4) | |
N1 | 0.7140 (4) | 0.36909 (14) | 0.54034 (9) | 0.0481 (4) | |
H1 | 0.8297 | 0.4205 | 0.5476 | 0.058* | |
N2 | 0.5577 (4) | 0.24761 (15) | 0.45933 (10) | 0.0517 (4) | |
H2 | 0.4722 | 0.2223 | 0.4998 | 0.062* | |
C1 | 0.9528 (12) | 0.8466 (4) | 1.0584 (2) | 0.1484 (18) | |
H1A | 0.8029 | 0.8256 | 1.0945 | 0.223* | |
H1B | 0.9753 | 0.9298 | 1.0616 | 0.223* | |
H1C | 1.1280 | 0.8006 | 1.0670 | 0.223* | |
C2 | 0.8783 (11) | 0.8216 (3) | 0.9835 (2) | 0.1307 (15) | |
H2A | 0.7070 | 0.8720 | 0.9745 | 0.157* | |
H2B | 1.0311 | 0.8436 | 0.9476 | 0.157* | |
C3 | 0.8308 (9) | 0.6977 (3) | 0.97181 (18) | 0.1074 (11) | |
H3A | 0.6837 | 0.6750 | 1.0091 | 0.129* | |
H3B | 1.0048 | 0.6479 | 0.9792 | 0.129* | |
C4 | 0.7440 (8) | 0.6707 (3) | 0.89723 (16) | 0.0951 (9) | |
H4A | 0.5734 | 0.7221 | 0.8889 | 0.114* | |
H4B | 0.8942 | 0.6900 | 0.8598 | 0.114* | |
C5 | 0.6872 (7) | 0.5449 (3) | 0.88831 (15) | 0.0873 (9) | |
H5A | 0.5416 | 0.5250 | 0.9269 | 0.105* | |
H5B | 0.8598 | 0.4939 | 0.8954 | 0.105* | |
C6 | 0.5922 (6) | 0.5167 (2) | 0.81562 (13) | 0.0747 (7) | |
H6A | 0.4186 | 0.5668 | 0.8084 | 0.090* | |
H6B | 0.7373 | 0.5360 | 0.7768 | 0.090* | |
C7 | 0.5383 (7) | 0.3888 (3) | 0.80900 (14) | 0.0787 (8) | |
H7A | 0.4022 | 0.3685 | 0.8498 | 0.094* | |
H7B | 0.7152 | 0.3394 | 0.8137 | 0.094* | |
C8 | 0.4263 (5) | 0.3578 (2) | 0.73827 (13) | 0.0658 (6) | |
H8A | 0.3892 | 0.2748 | 0.7406 | 0.079* | |
H8B | 0.2470 | 0.4055 | 0.7335 | 0.079* | |
C9 | 0.6313 (5) | 0.3787 (2) | 0.67181 (12) | 0.0550 (6) | |
H9A | 0.6436 | 0.4637 | 0.6655 | 0.066* | |
H9B | 0.8189 | 0.3422 | 0.6807 | 0.066* | |
C10 | 0.5548 (4) | 0.33149 (18) | 0.60210 (12) | 0.0502 (5) | |
C11 | 0.7161 (4) | 0.33642 (17) | 0.46781 (11) | 0.0448 (5) | |
C12 | 0.5032 (4) | 0.18709 (18) | 0.39686 (12) | 0.0478 (5) | |
C13 | 0.3189 (4) | 0.09942 (18) | 0.41067 (12) | 0.0499 (5) | |
H13 | 0.2411 | 0.0848 | 0.4585 | 0.060* | |
C14 | 0.2497 (4) | 0.03368 (18) | 0.35420 (13) | 0.0515 (5) | |
C15 | 0.3639 (5) | 0.0554 (2) | 0.28369 (13) | 0.0600 (6) | |
C16 | 0.5490 (6) | 0.1417 (2) | 0.26975 (14) | 0.0665 (7) | |
H16 | 0.6266 | 0.1557 | 0.2218 | 0.080* | |
C17 | 0.6212 (5) | 0.2079 (2) | 0.32576 (13) | 0.0613 (6) | |
H17 | 0.7476 | 0.2657 | 0.3159 | 0.074* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0635 (4) | 0.0518 (3) | 0.0937 (5) | −0.0211 (3) | −0.0138 (3) | −0.0129 (3) |
Cl2 | 0.1279 (7) | 0.0942 (5) | 0.0775 (5) | −0.0338 (5) | −0.0231 (4) | −0.0307 (4) |
S1 | 0.0643 (4) | 0.0517 (3) | 0.0606 (4) | −0.0245 (3) | −0.0003 (3) | −0.0033 (3) |
O1 | 0.0618 (10) | 0.0693 (10) | 0.0627 (10) | −0.0372 (8) | −0.0035 (8) | −0.0062 (8) |
N1 | 0.0472 (10) | 0.0453 (9) | 0.0553 (11) | −0.0194 (8) | −0.0065 (8) | −0.0065 (8) |
N2 | 0.0549 (11) | 0.0517 (10) | 0.0523 (10) | −0.0232 (9) | −0.0059 (8) | −0.0036 (8) |
C1 | 0.246 (5) | 0.117 (3) | 0.099 (3) | −0.070 (3) | −0.043 (3) | −0.014 (2) |
C2 | 0.205 (5) | 0.100 (3) | 0.100 (3) | −0.049 (3) | −0.042 (3) | −0.010 (2) |
C3 | 0.158 (3) | 0.092 (2) | 0.081 (2) | −0.035 (2) | −0.033 (2) | −0.0059 (17) |
C4 | 0.134 (3) | 0.089 (2) | 0.0673 (18) | −0.0217 (19) | −0.0211 (18) | −0.0084 (15) |
C5 | 0.118 (2) | 0.091 (2) | 0.0575 (16) | −0.0275 (18) | −0.0122 (16) | −0.0076 (14) |
C6 | 0.096 (2) | 0.0782 (18) | 0.0521 (14) | −0.0202 (15) | −0.0076 (13) | −0.0066 (12) |
C7 | 0.098 (2) | 0.089 (2) | 0.0534 (15) | −0.0347 (16) | −0.0063 (14) | 0.0052 (13) |
C8 | 0.0718 (16) | 0.0731 (16) | 0.0562 (14) | −0.0297 (13) | −0.0043 (12) | 0.0029 (12) |
C9 | 0.0527 (13) | 0.0580 (13) | 0.0576 (13) | −0.0179 (10) | −0.0080 (10) | −0.0038 (10) |
C10 | 0.0464 (12) | 0.0463 (12) | 0.0600 (14) | −0.0113 (10) | −0.0082 (10) | −0.0035 (10) |
C11 | 0.0399 (11) | 0.0372 (10) | 0.0588 (13) | −0.0051 (8) | −0.0092 (9) | −0.0042 (9) |
C12 | 0.0480 (12) | 0.0434 (11) | 0.0541 (13) | −0.0087 (9) | −0.0108 (10) | −0.0039 (9) |
C13 | 0.0472 (12) | 0.0451 (11) | 0.0584 (13) | −0.0068 (9) | −0.0074 (10) | −0.0050 (10) |
C14 | 0.0479 (12) | 0.0414 (11) | 0.0682 (15) | −0.0083 (9) | −0.0140 (11) | −0.0081 (10) |
C15 | 0.0673 (15) | 0.0541 (13) | 0.0625 (15) | −0.0081 (11) | −0.0190 (12) | −0.0138 (11) |
C16 | 0.0820 (17) | 0.0647 (15) | 0.0558 (14) | −0.0194 (13) | −0.0082 (12) | −0.0041 (11) |
C17 | 0.0717 (16) | 0.0548 (13) | 0.0608 (15) | −0.0220 (12) | −0.0080 (12) | −0.0013 (11) |
Cl1—C14 | 1.724 (2) | C5—H5A | 0.9700 |
Cl2—C15 | 1.736 (2) | C5—H5B | 0.9700 |
S1—C11 | 1.655 (2) | C6—C7 | 1.503 (4) |
O1—C10 | 1.219 (2) | C6—H6A | 0.9700 |
N1—C10 | 1.371 (3) | C6—H6B | 0.9700 |
N1—C11 | 1.389 (3) | C7—C8 | 1.515 (3) |
N1—H1 | 0.8600 | C7—H7A | 0.9700 |
N2—C11 | 1.333 (2) | C7—H7B | 0.9700 |
N2—C12 | 1.411 (2) | C8—C9 | 1.501 (3) |
N2—H2 | 0.8600 | C8—H8A | 0.9700 |
C1—C2 | 1.495 (4) | C8—H8B | 0.9700 |
C1—H1A | 0.9600 | C9—C10 | 1.492 (3) |
C1—H1B | 0.9600 | C9—H9A | 0.9700 |
C1—H1C | 0.9600 | C9—H9B | 0.9700 |
C2—C3 | 1.465 (4) | C12—C17 | 1.384 (3) |
C2—H2A | 0.9700 | C12—C13 | 1.384 (3) |
C2—H2B | 0.9700 | C13—C14 | 1.378 (3) |
C3—C4 | 1.517 (4) | C13—H13 | 0.9300 |
C3—H3A | 0.9700 | C14—C15 | 1.370 (3) |
C3—H3B | 0.9700 | C15—C16 | 1.375 (3) |
C4—C5 | 1.489 (4) | C16—C17 | 1.379 (3) |
C4—H4A | 0.9700 | C16—H16 | 0.9300 |
C4—H4B | 0.9700 | C17—H17 | 0.9300 |
C5—C6 | 1.504 (3) | ||
C10—N1—C11 | 129.58 (17) | C6—C7—C8 | 115.6 (2) |
C10—N1—H1 | 115.2 | C6—C7—H7A | 108.4 |
C11—N1—H1 | 115.2 | C8—C7—H7A | 108.4 |
C11—N2—C12 | 132.43 (18) | C6—C7—H7B | 108.4 |
C11—N2—H2 | 113.8 | C8—C7—H7B | 108.4 |
C12—N2—H2 | 113.8 | H7A—C7—H7B | 107.4 |
C2—C1—H1A | 109.5 | C9—C8—C7 | 112.5 (2) |
C2—C1—H1B | 109.5 | C9—C8—H8A | 109.1 |
H1A—C1—H1B | 109.5 | C7—C8—H8A | 109.1 |
C2—C1—H1C | 109.5 | C9—C8—H8B | 109.1 |
H1A—C1—H1C | 109.5 | C7—C8—H8B | 109.1 |
H1B—C1—H1C | 109.5 | H8A—C8—H8B | 107.8 |
C3—C2—C1 | 115.0 (3) | C10—C9—C8 | 114.85 (18) |
C3—C2—H2A | 108.5 | C10—C9—H9A | 108.6 |
C1—C2—H2A | 108.5 | C8—C9—H9A | 108.6 |
C3—C2—H2B | 108.5 | C10—C9—H9B | 108.6 |
C1—C2—H2B | 108.5 | C8—C9—H9B | 108.6 |
H2A—C2—H2B | 107.5 | H9A—C9—H9B | 107.5 |
C2—C3—C4 | 116.1 (3) | O1—C10—N1 | 122.20 (19) |
C2—C3—H3A | 108.3 | O1—C10—C9 | 123.8 (2) |
C4—C3—H3A | 108.3 | N1—C10—C9 | 114.00 (17) |
C2—C3—H3B | 108.3 | N2—C11—N1 | 113.74 (18) |
C4—C3—H3B | 108.3 | N2—C11—S1 | 128.19 (16) |
H3A—C3—H3B | 107.4 | N1—C11—S1 | 118.06 (14) |
C5—C4—C3 | 114.6 (3) | C17—C12—C13 | 119.6 (2) |
C5—C4—H4A | 108.6 | C17—C12—N2 | 125.30 (19) |
C3—C4—H4A | 108.6 | C13—C12—N2 | 115.07 (18) |
C5—C4—H4B | 108.6 | C14—C13—C12 | 120.6 (2) |
C3—C4—H4B | 108.6 | C14—C13—H13 | 119.7 |
H4A—C4—H4B | 107.6 | C12—C13—H13 | 119.7 |
C4—C5—C6 | 115.6 (2) | C15—C14—C13 | 119.7 (2) |
C4—C5—H5A | 108.4 | C15—C14—Cl1 | 121.13 (17) |
C6—C5—H5A | 108.4 | C13—C14—Cl1 | 119.17 (18) |
C4—C5—H5B | 108.4 | C14—C15—C16 | 119.9 (2) |
C6—C5—H5B | 108.4 | C14—C15—Cl2 | 121.17 (18) |
H5A—C5—H5B | 107.4 | C16—C15—Cl2 | 118.9 (2) |
C7—C6—C5 | 113.8 (2) | C15—C16—C17 | 121.0 (2) |
C7—C6—H6A | 108.8 | C15—C16—H16 | 119.5 |
C5—C6—H6A | 108.8 | C17—C16—H16 | 119.5 |
C7—C6—H6B | 108.8 | C16—C17—C12 | 119.1 (2) |
C5—C6—H6B | 108.8 | C16—C17—H17 | 120.4 |
H6A—C6—H6B | 107.7 | C12—C17—H17 | 120.4 |
C1—C2—C3—C4 | 177.8 (4) | C11—N2—C12—C17 | 2.1 (4) |
C2—C3—C4—C5 | −177.9 (4) | C11—N2—C12—C13 | −178.9 (2) |
C3—C4—C5—C6 | 178.2 (3) | C17—C12—C13—C14 | −0.7 (3) |
C4—C5—C6—C7 | 179.8 (3) | N2—C12—C13—C14 | −179.76 (17) |
C5—C6—C7—C8 | 176.7 (3) | C12—C13—C14—C15 | −0.1 (3) |
C6—C7—C8—C9 | 61.8 (3) | C12—C13—C14—Cl1 | −179.65 (17) |
C7—C8—C9—C10 | 170.5 (2) | C13—C14—C15—C16 | 0.7 (3) |
C11—N1—C10—O1 | −3.9 (3) | Cl1—C14—C15—C16 | −179.83 (19) |
C11—N1—C10—C9 | 174.66 (19) | C13—C14—C15—Cl2 | −179.33 (16) |
C8—C9—C10—O1 | −12.4 (3) | Cl1—C14—C15—Cl2 | 0.2 (3) |
C8—C9—C10—N1 | 169.1 (2) | C14—C15—C16—C17 | −0.4 (4) |
C12—N2—C11—N1 | −179.19 (19) | Cl2—C15—C16—C17 | 179.6 (2) |
C12—N2—C11—S1 | −0.6 (3) | C15—C16—C17—C12 | −0.4 (4) |
C10—N1—C11—N2 | −6.8 (3) | C13—C12—C17—C16 | 1.0 (3) |
C10—N1—C11—S1 | 174.47 (17) | N2—C12—C17—C16 | 179.9 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O1 | 0.86 | 1.90 | 2.627 (2) | 142 |
C17—H17···S1 | 0.93 | 2.54 | 3.207 (3) | 129 |
N1—H1···S1i | 0.86 | 2.62 | 3.461 (2) | 166 |
C9—H9A···S1i | 0.97 | 2.84 | 3.552 (3) | 131 |
Symmetry code: (i) −x+2, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C17H24Cl2N2OS |
Mr | 375.34 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 4.7368 (13), 11.295 (3), 18.324 (5) |
α, β, γ (°) | 88.289 (5), 83.774 (5), 84.268 (4) |
V (Å3) | 969.5 (5) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.45 |
Crystal size (mm) | 0.46 × 0.41 × 0.09 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 2000) |
Tmin, Tmax | 0.821, 0.961 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10011, 3778, 2856 |
Rint | 0.027 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.045, 0.115, 1.04 |
No. of reflections | 3778 |
No. of parameters | 209 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.26, −0.15 |
Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SAINT, SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b), SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O1 | 0.86 | 1.90 | 2.627 (2) | 142 |
C17—H17···S1 | 0.93 | 2.54 | 3.207 (3) | 129 |
N1—H1···S1i | 0.86 | 2.62 | 3.461 (2) | 166 |
C9—H9A···S1i | 0.97 | 2.84 | 3.552 (3) | 131 |
Symmetry code: (i) −x+2, −y+1, −z+1. |
Thiourea derivatives receive considerable attention because of their potential applications in materials science (Wei et al., 2004) and their biological activities (Baruah et al., 2002). The title compound, (I), is similar to N-(3,4-Dichlorophenyl)-N'-(3-nitrobenzoyl)thiourea, (Yusof et al., 2006), except that the 3-nitrobenzoyl group is replaced by a decanoyl group (Fig.1). The molecule maintains its trans-cis configuration with respect to the position of the decanoyl and 3,4-dichlorophenyl groups relative to the thiono S1 atom across their C—N bonds, respectively. The bond lengths and angles are in normal ranges (Allen et al., 1987) and comparable with other thiourea derivatives (Yusof, Ramlee et al. (2007); Yusof, Yaakob et al. (2007). The thiourea-3,4-dichlorophenyl (S1/N1/N2/C11—C17/Cl1/Cl2) fragment are essentially planar with a maximum deviation of 0.039 (2) Å for atom C10 from the least-squares plane.
There are two intramolecular hydrogen bonds, N2—H2···O1 and C17—H17···S1 (Table 2), forming two pseudo-six-membered rings (O1···H2—N2—C11—N1—C10—O1 and S1···H17—C17—C12—N2—C11—S1). In the crystal structure, the molecules are linked by intermolecular interactions, N—H···S and C—H···S (symmetry codes as in Table 2) forming dimers parallel to b axis (Fig.2).