organic compounds
N-[(2,4-Dimethylphenyl)carbamothioyl]-2-methylbenzamide
aSchool of Chemical Sciences and Food Technology, Universiti Kebangsaan Malaysia, UKM 43650 Bangi Selangor, Malaysia, bHEJ Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan, and cDepartment of Chemistry, Universiti Malaysia Terengganu, Manngabang Telipot, Terengganu, Malaysia
*Correspondence e-mail: sammer_yousuf@yahoo.com
The title compound, C17H18N2OS, adopts a trans–cis geometry of the thiourea group which is stabilized by intramolecular hydrogen bonds between the O atom of the carbonyl group and the H atom of the thioamide group. A C—H⋯S intramolecular hydrogen bond is also present. In the molecules are linked by intermolecular N—H⋯S hydrogen bonds to form centrosymmetric dimers.
Related literature
For the et al. (2007). For bond-length data, see: Allen et al. (1987).
of 1-(2,3-dimethylphenyl)-3-(2-methylbenzoyl)thiourea, which is isomeric with the title compound, see: Khawar RaufExperimental
Crystal data
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Refinement
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Data collection: SMART (Bruker, 2000); cell SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).
Supporting information
10.1107/S1600536808009501/at2557sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808009501/at2557Isup2.hkl
The mixture of 2-methylbenzoyl chloride (9.720 g, 0.025 mol) with the equimolar amount of ammonium thiocyanate (1.903 g, 0.025 mol) and 2,3-dimethyl aniline (3.025 g, 0.025 mol) in 40 ml dry acetone was refluxed with stirring for 4 h. The solution was filtered and left to evaporate at room temperature. The colourless crystals obtained after a few days, was found suitable for X-ray investigations. The yield was 85% with melting point 413.2–415.7 K.
H atoms on the C and N parent atoms were positioned geomatrically, with C—H = 0.96, 0.93 and N—H = 0.86Å
and constrained to ride on their parent atoms with Uiso(H) = 1.2Ueq(CH and NH) and 1.5Ueq(CH3).
Data collection: SMART (Bruker, 2000); cell
SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2003).C17H18N2OS | Z = 2 |
Mr = 298.39 | F(000) = 316 |
Triclinic, P1 | Dx = 1.269 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 6.2569 (15) Å | Cell parameters from 1377 reflections |
b = 9.862 (2) Å | θ = 1.5–25.5° |
c = 13.986 (3) Å | µ = 0.21 mm−1 |
α = 69.461 (4)° | T = 298 K |
β = 86.199 (4)° | Slab, colourless |
γ = 75.206 (4)° | 0.27 × 0.18 × 0.09 mm |
V = 781.1 (3) Å3 |
Bruker SMART APEX CCD area-detector diffractometer | 2904 independent reflections |
Radiation source: fine-focus sealed tube | 2069 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.034 |
Detector resolution: 83.66 pixels mm-1 | θmax = 25.5°, θmin = 1.5° |
ω scans | h = −7→7 |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | k = −11→11 |
Tmin = 0.946, Tmax = 0.982 | l = −16→16 |
7817 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)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.119 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0567P)2 + 0.1084P] where P = (Fo2 + 2Fc2)/3 |
2904 reflections | (Δ/σ)max = 0.001 |
193 parameters | Δρmax = 0.23 e Å−3 |
0 restraints | Δρmin = −0.17 e Å−3 |
C17H18N2OS | γ = 75.206 (4)° |
Mr = 298.39 | V = 781.1 (3) Å3 |
Triclinic, P1 | Z = 2 |
a = 6.2569 (15) Å | Mo Kα radiation |
b = 9.862 (2) Å | µ = 0.21 mm−1 |
c = 13.986 (3) Å | T = 298 K |
α = 69.461 (4)° | 0.27 × 0.18 × 0.09 mm |
β = 86.199 (4)° |
Bruker SMART APEX CCD area-detector diffractometer | 2904 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | 2069 reflections with I > 2σ(I) |
Tmin = 0.946, Tmax = 0.982 | Rint = 0.034 |
7817 measured reflections |
R[F2 > 2σ(F2)] = 0.047 | 0 restraints |
wR(F2) = 0.119 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.23 e Å−3 |
2904 reflections | Δρmin = −0.17 e Å−3 |
193 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 | ||
S1 | 0.00124 (10) | 0.51524 (6) | 0.34145 (4) | 0.0441 (2) | |
O1 | 0.2196 (3) | 0.02671 (18) | 0.54848 (13) | 0.0630 (5) | |
N1 | 0.1412 (3) | 0.27939 (19) | 0.50519 (13) | 0.0374 (4) | |
H1 | 0.1341 | 0.3473 | 0.5313 | 0.045* | |
N2 | 0.0595 (3) | 0.22917 (19) | 0.36460 (13) | 0.0394 (5) | |
H2 | 0.0883 | 0.1375 | 0.4048 | 0.047* | |
C1 | 0.2131 (4) | 0.0521 (3) | 0.75752 (18) | 0.0519 (6) | |
H1A | 0.1042 | 0.0051 | 0.7537 | 0.062* | |
C2 | 0.2787 (5) | 0.0473 (3) | 0.85127 (19) | 0.0644 (8) | |
H2A | 0.2120 | −0.0007 | 0.9105 | 0.077* | |
C3 | 0.4424 (5) | 0.1138 (3) | 0.8562 (2) | 0.0639 (8) | |
H3 | 0.4864 | 0.1112 | 0.9192 | 0.077* | |
C4 | 0.5414 (4) | 0.1835 (3) | 0.77013 (19) | 0.0541 (7) | |
H4 | 0.6543 | 0.2264 | 0.7754 | 0.065* | |
C5 | 0.4783 (4) | 0.1923 (3) | 0.67457 (17) | 0.0430 (6) | |
C6 | 0.3089 (3) | 0.1265 (2) | 0.66943 (16) | 0.0367 (5) | |
C7 | 0.5968 (5) | 0.2679 (4) | 0.5822 (2) | 0.0696 (8) | |
H7A | 0.5020 | 0.3625 | 0.5433 | 0.104* | |
H7B | 0.6355 | 0.2060 | 0.5407 | 0.104* | |
H7C | 0.7286 | 0.2835 | 0.6034 | 0.104* | |
C8 | 0.2225 (4) | 0.1361 (2) | 0.56942 (17) | 0.0393 (5) | |
C9 | 0.0679 (3) | 0.3321 (2) | 0.40383 (15) | 0.0334 (5) | |
C10 | 0.0056 (4) | 0.2603 (2) | 0.25979 (16) | 0.0366 (5) | |
C11 | 0.1738 (4) | 0.2193 (3) | 0.19879 (18) | 0.0473 (6) | |
H11 | 0.3167 | 0.1740 | 0.2259 | 0.057* | |
C12 | 0.1297 (4) | 0.2456 (3) | 0.09727 (19) | 0.0538 (7) | |
H12 | 0.2440 | 0.2181 | 0.0565 | 0.065* | |
C13 | −0.0810 (4) | 0.3119 (3) | 0.05573 (17) | 0.0499 (6) | |
C14 | −0.2460 (4) | 0.3481 (3) | 0.11976 (17) | 0.0463 (6) | |
H14 | −0.3895 | 0.3910 | 0.0929 | 0.056* | |
C15 | −0.2098 (4) | 0.3239 (2) | 0.22153 (16) | 0.0394 (5) | |
C16 | −0.1300 (5) | 0.3419 (3) | −0.05520 (19) | 0.0748 (9) | |
H16A | −0.0953 | 0.4338 | −0.0968 | 0.112* | |
H16B | −0.2839 | 0.3494 | −0.0643 | 0.112* | |
H16C | −0.0420 | 0.2614 | −0.0750 | 0.112* | |
C17 | −0.3997 (4) | 0.3598 (3) | 0.28774 (19) | 0.0564 (7) | |
H17A | −0.5362 | 0.3917 | 0.2493 | 0.085* | |
H17B | −0.3828 | 0.4383 | 0.3099 | 0.085* | |
H17C | −0.4015 | 0.2723 | 0.3462 | 0.085* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0630 (4) | 0.0333 (3) | 0.0343 (3) | −0.0086 (3) | −0.0061 (3) | −0.0108 (2) |
O1 | 0.1010 (14) | 0.0356 (9) | 0.0529 (11) | −0.0138 (9) | −0.0262 (10) | −0.0130 (8) |
N1 | 0.0502 (11) | 0.0303 (9) | 0.0333 (10) | −0.0070 (8) | −0.0101 (8) | −0.0128 (8) |
N2 | 0.0524 (12) | 0.0300 (9) | 0.0347 (10) | −0.0063 (8) | −0.0104 (8) | −0.0107 (8) |
C1 | 0.0657 (16) | 0.0445 (14) | 0.0448 (15) | −0.0180 (12) | −0.0029 (12) | −0.0108 (12) |
C2 | 0.092 (2) | 0.0591 (17) | 0.0327 (14) | −0.0153 (16) | 0.0040 (14) | −0.0072 (13) |
C3 | 0.089 (2) | 0.0587 (17) | 0.0398 (16) | −0.0019 (16) | −0.0202 (15) | −0.0193 (13) |
C4 | 0.0576 (16) | 0.0573 (16) | 0.0483 (16) | −0.0066 (13) | −0.0184 (13) | −0.0214 (13) |
C5 | 0.0421 (13) | 0.0453 (14) | 0.0402 (14) | −0.0053 (11) | −0.0066 (11) | −0.0157 (11) |
C6 | 0.0424 (13) | 0.0311 (11) | 0.0339 (12) | −0.0037 (10) | −0.0052 (10) | −0.0109 (10) |
C7 | 0.0598 (17) | 0.101 (2) | 0.0598 (18) | −0.0409 (16) | 0.0074 (14) | −0.0278 (17) |
C8 | 0.0450 (13) | 0.0363 (12) | 0.0380 (13) | −0.0111 (10) | −0.0058 (10) | −0.0127 (10) |
C9 | 0.0319 (11) | 0.0387 (12) | 0.0313 (12) | −0.0077 (9) | −0.0019 (9) | −0.0144 (10) |
C10 | 0.0494 (14) | 0.0326 (11) | 0.0315 (12) | −0.0110 (10) | −0.0056 (10) | −0.0135 (9) |
C11 | 0.0478 (14) | 0.0472 (14) | 0.0487 (15) | −0.0026 (11) | −0.0052 (12) | −0.0239 (12) |
C12 | 0.0579 (17) | 0.0569 (16) | 0.0475 (15) | −0.0036 (13) | 0.0052 (13) | −0.0274 (13) |
C13 | 0.0694 (17) | 0.0452 (14) | 0.0338 (13) | −0.0083 (12) | −0.0056 (12) | −0.0152 (11) |
C14 | 0.0504 (14) | 0.0455 (14) | 0.0404 (14) | −0.0049 (11) | −0.0128 (11) | −0.0143 (11) |
C15 | 0.0428 (13) | 0.0400 (12) | 0.0361 (13) | −0.0090 (10) | −0.0031 (10) | −0.0141 (10) |
C16 | 0.101 (2) | 0.080 (2) | 0.0370 (15) | −0.0053 (17) | −0.0084 (15) | −0.0226 (14) |
C17 | 0.0470 (15) | 0.0767 (19) | 0.0493 (16) | −0.0126 (13) | −0.0008 (12) | −0.0279 (14) |
S1—C9 | 1.660 (2) | C7—H7A | 0.9600 |
O1—C8 | 1.218 (3) | C7—H7B | 0.9600 |
N1—C8 | 1.366 (3) | C7—H7C | 0.9600 |
N1—C9 | 1.392 (3) | C10—C11 | 1.380 (3) |
N1—H1 | 0.8600 | C10—C15 | 1.387 (3) |
N2—C9 | 1.325 (3) | C11—C12 | 1.384 (3) |
N2—C10 | 1.433 (3) | C11—H11 | 0.9300 |
N2—H2 | 0.8600 | C12—C13 | 1.378 (3) |
C1—C6 | 1.381 (3) | C12—H12 | 0.9300 |
C1—C2 | 1.381 (3) | C13—C14 | 1.381 (3) |
C1—H1A | 0.9300 | C13—C16 | 1.511 (3) |
C2—C3 | 1.367 (4) | C14—C15 | 1.383 (3) |
C2—H2A | 0.9300 | C14—H14 | 0.9300 |
C3—C4 | 1.358 (4) | C15—C17 | 1.505 (3) |
C3—H3 | 0.9300 | C16—H16A | 0.9600 |
C4—C5 | 1.386 (3) | C16—H16B | 0.9600 |
C4—H4 | 0.9300 | C16—H16C | 0.9600 |
C5—C6 | 1.395 (3) | C17—H17A | 0.9600 |
C5—C7 | 1.501 (3) | C17—H17B | 0.9600 |
C6—C8 | 1.496 (3) | C17—H17C | 0.9600 |
C8—N1—C9 | 129.81 (17) | N2—C9—N1 | 116.13 (18) |
C8—N1—H1 | 115.1 | N2—C9—S1 | 125.20 (16) |
C9—N1—H1 | 115.1 | N1—C9—S1 | 118.67 (15) |
C9—N2—C10 | 124.43 (18) | C11—C10—C15 | 120.8 (2) |
C9—N2—H2 | 117.8 | C11—C10—N2 | 117.8 (2) |
C10—N2—H2 | 117.8 | C15—C10—N2 | 121.3 (2) |
C6—C1—C2 | 120.2 (2) | C10—C11—C12 | 120.0 (2) |
C6—C1—H1A | 119.9 | C10—C11—H11 | 120.0 |
C2—C1—H1A | 119.9 | C12—C11—H11 | 120.0 |
C3—C2—C1 | 119.4 (2) | C13—C12—C11 | 121.0 (2) |
C3—C2—H2A | 120.3 | C13—C12—H12 | 119.5 |
C1—C2—H2A | 120.3 | C11—C12—H12 | 119.5 |
C4—C3—C2 | 120.7 (2) | C12—C13—C14 | 117.4 (2) |
C4—C3—H3 | 119.7 | C12—C13—C16 | 121.2 (2) |
C2—C3—H3 | 119.7 | C14—C13—C16 | 121.4 (2) |
C3—C4—C5 | 121.6 (2) | C13—C14—C15 | 123.6 (2) |
C3—C4—H4 | 119.2 | C13—C14—H14 | 118.2 |
C5—C4—H4 | 119.2 | C15—C14—H14 | 118.2 |
C4—C5—C6 | 117.7 (2) | C14—C15—C10 | 117.2 (2) |
C4—C5—C7 | 119.4 (2) | C14—C15—C17 | 120.6 (2) |
C6—C5—C7 | 122.9 (2) | C10—C15—C17 | 122.2 (2) |
C1—C6—C5 | 120.4 (2) | C13—C16—H16A | 109.5 |
C1—C6—C8 | 118.0 (2) | C13—C16—H16B | 109.5 |
C5—C6—C8 | 121.57 (19) | H16A—C16—H16B | 109.5 |
C5—C7—H7A | 109.5 | C13—C16—H16C | 109.5 |
C5—C7—H7B | 109.5 | H16A—C16—H16C | 109.5 |
H7A—C7—H7B | 109.5 | H16B—C16—H16C | 109.5 |
C5—C7—H7C | 109.5 | C15—C17—H17A | 109.5 |
H7A—C7—H7C | 109.5 | C15—C17—H17B | 109.5 |
H7B—C7—H7C | 109.5 | H17A—C17—H17B | 109.5 |
O1—C8—N1 | 123.27 (19) | C15—C17—H17C | 109.5 |
O1—C8—C6 | 123.18 (19) | H17A—C17—H17C | 109.5 |
N1—C8—C6 | 113.52 (18) | H17B—C17—H17C | 109.5 |
C6—C1—C2—C3 | −1.5 (4) | C10—N2—C9—S1 | 4.5 (3) |
C1—C2—C3—C4 | −0.3 (4) | C8—N1—C9—N2 | 5.5 (3) |
C2—C3—C4—C5 | 1.2 (4) | C8—N1—C9—S1 | −173.80 (17) |
C3—C4—C5—C6 | −0.2 (3) | C9—N2—C10—C11 | 108.4 (2) |
C3—C4—C5—C7 | −178.7 (3) | C9—N2—C10—C15 | −74.2 (3) |
C2—C1—C6—C5 | 2.5 (3) | C15—C10—C11—C12 | 1.9 (3) |
C2—C1—C6—C8 | −176.4 (2) | N2—C10—C11—C12 | 179.4 (2) |
C4—C5—C6—C1 | −1.7 (3) | C10—C11—C12—C13 | −0.3 (4) |
C7—C5—C6—C1 | 176.8 (2) | C11—C12—C13—C14 | −1.3 (4) |
C4—C5—C6—C8 | 177.2 (2) | C11—C12—C13—C16 | 179.6 (2) |
C7—C5—C6—C8 | −4.3 (3) | C12—C13—C14—C15 | 1.3 (4) |
C9—N1—C8—O1 | −8.8 (4) | C16—C13—C14—C15 | −179.6 (2) |
C9—N1—C8—C6 | 173.14 (19) | C13—C14—C15—C10 | 0.3 (3) |
C1—C6—C8—O1 | −57.8 (3) | C13—C14—C15—C17 | −177.2 (2) |
C5—C6—C8—O1 | 123.3 (3) | C11—C10—C15—C14 | −1.9 (3) |
C1—C6—C8—N1 | 120.3 (2) | N2—C10—C15—C14 | −179.21 (19) |
C5—C6—C8—N1 | −58.6 (3) | C11—C10—C15—C17 | 175.5 (2) |
C10—N2—C9—N1 | −174.81 (18) | N2—C10—C15—C17 | −1.8 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O1 | 0.86 | 2.03 | 2.706 | 135 |
C17—H17B···S1 | 0.96 | 2.80 | 3.496 | 130 |
N1—H1···S1i | 0.86 | 2.57 | 3.372 | 155 |
Symmetry code: (i) −x, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C17H18N2OS |
Mr | 298.39 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 298 |
a, b, c (Å) | 6.2569 (15), 9.862 (2), 13.986 (3) |
α, β, γ (°) | 69.461 (4), 86.199 (4), 75.206 (4) |
V (Å3) | 781.1 (3) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.21 |
Crystal size (mm) | 0.27 × 0.18 × 0.09 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2000) |
Tmin, Tmax | 0.946, 0.982 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7817, 2904, 2069 |
Rint | 0.034 |
(sin θ/λ)max (Å−1) | 0.606 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.047, 0.119, 1.02 |
No. of reflections | 2904 |
No. of parameters | 193 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.23, −0.17 |
Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O1 | 0.86 | 2.03 | 2.706 | 135 |
C17—H17B···S1 | 0.96 | 2.80 | 3.496 | 130 |
N1—H1···S1i | 0.86 | 2.57 | 3.372 | 155 |
Symmetry code: (i) −x, −y+1, −z+1. |
Acknowledgements
The authors thank the Ministry of Higher Education of Malaysia for Fundamental Research Grants OUP UKM-OUP-BIT-28/20076 and UMT-FRGS-59001, and Universiti Kebangsaan Malaysia and HEJ Research Institute of Chemistry, University of Karachi, for research facilities.
References
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Khawar Rauf, M., Badshah, A. & Bolte, M. (2007). Acta Cryst. E63, o1256–o1257. Web of Science CSD CrossRef IUCr Journals Google Scholar
Nardelli, M. (1995). J. Appl. Cryst. 28, 659. CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar
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The title compound, (I), is isomeric to the previously reported 1-(2,3-dimethylphenyl)-3-(2-methylbenzoyl)thiourea (II), (Khawar Rauf et al., 2007) with the difference that the 2,3-dimethylphenyl ring is replaced by 2,4-dimethylphenyl (Fig.1). The bond lengths and angles are in normal range (Allen et al., 1987) and in agreement with those in (II). The central thiourea moiety (S1/N1/N2/C9), 2-methylbenzoyl (C1—C8), and 2,3-dimethylphenyl (C10—C15) rings are each planar with a maximum deviation of 0.040 (2)Å for C8 atom from the least square plane. The dihedral angles between the thiourea moiety and the 2-methylbenzoyl and 2,3-dimethylphenyl rings are 52.96 (11) and 70.34 (12)°, respectively. The trans-cis geometry of the thiourea moiety is stabilized by N2—H2···O1 and C17—H17B···S1 intramolecular hydrogen bonds. In the crystal structure, the molecules are linked to form dimers by the N1—H1···S1 intermolecular hydrogen bond (symmtery codes as in Table 2) and arranged parallel to c axis (Fig.2).