1-(3,5-Dimethyl­phen­yl)-3-phenyl­thio­urea

The title compound, C₁₅H₁₆N₂S, was prepared by the reaction of 3,5-dimethyl­phenyl­amine with 1-isothio­cyanato­benzene. In the mol­ecule, all bond lengths and angles are within normal ranges. The dihedral angle between the two aromatic rings is 48.77 (1)°. The crystal packing is stabilized by van der Waals forces.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.043
• wR factor = 0.135
• Data-to-parameter ratio = 18.3

checkCIF/PLATON results

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Alert level C
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000)        3000 Deg.
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety         C1
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety         C2
PLAT420_ALERT_2_C D-H Without Acceptor       N1     -   H1A    ...          ?

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
   5 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

Thiosemicarbazides are able to form complexes with biological activities (Shen et al., 1998). Thiourea derivatives have been successful screened for various biological activities (Antholine & Taketa,1982), and some of them have shown promising anti-HIV properties (Mao et al., 1999). The title compound was synthesized as part of our study of these ligands. Here we report the crystal structure of (I).

In (I) (Fig. 1),the bond lengths and angles are usual for this type of compound (Ji et al., 2002). The mean planes p1(S1,N1,N2,C8,C9,C10) and p2 (N1,C1,C2,C3,C4,C5,C6,C7) make a dihedral angle of 59.69 (1)°. The dihedral angles formed by phenyl ring (C3,C4,C5,C6,C7,C8) and phenyl ring (C10,C11,C12,C13,C14,C15) with p1 are 59.82 (2)and 52.72 (2)° respectively. The dihedral angles between the benzene rings is 48.77 (1)°. The crystal packing is stabilized by van der Waals forces.

Related literature

For related literature, see: Antholine & Taketa (1982); Ji et al. (2002); Mao et al. (1999); Shen et al. (1998).

S2. Experimental

A mixture of 3,5-Dimethyl-phenylamine (0.02 mol) and 1-isothiocyanatobenzeneat (0.02 mol) was stirred in refluxing ethanol (30 ml) for 0.5 h to afford the title compound (4.35 g, yield 85%). Single crystals suitable for X-ray measurementswere obtained by recrystallization from ethanol at room temperature.

S3. Refinement

H atoms were fixed geometrically and allowed to ride on their parent atoms, with N—H and C—H distances of 0.86 and 0.93–0.96 Å, respectively, and with U_iso=1.2–1.5U_eq of the parent atoms.

Computing details

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: NRCVAX (Gabe et al., 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1990); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures

Fig. 1. The molecular structure and atom-labeling scheme for (I), with displacement ellipsoids drawn at the 30% probability level.

1-(3,5-Dimethylphenyl)-3-phenylthiourea

Crystal data

C15H16N2S	Z = 2
Mr = 256.36	F(000) = 272
Triclinic, P1	Dx = 1.197 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.3740 (17) Å	Cell parameters from 25 reflections
b = 9.1870 (18) Å	θ = 4–14°
c = 9.889 (2) Å	µ = 0.21 mm^−1
α = 107.57 (3)°	T = 293 K
β = 98.57 (3)°	Block, colourless
γ = 94.42 (3)°	0.20 × 0.18 × 0.15 mm
V = 711.2 (2) Å^3

Data collection

Enraf–Nonius CAD-4 diffractometer	Rint = 0.014
Radiation source: fine-focus sealed tube	θmax = 27.0°, θmin = 2.2°
Graphite monochromator	h = 0→9
ω scans	k = −10→10
3177 measured reflections	l = −11→11
2975 independent reflections	3 standard reflections every 100 reflections
2373 reflections with I > 2σ(I)	intensity decay: none

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.135	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0792P)^2 + 0.1571P] where P = (Fo^2 + 2Fc^2)/3
2975 reflections	(Δ/σ)max < 0.001
163 parameters	Δρmax = 0.28 e Å^−3
0 restraints	Δρmin = −0.26 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
S1	0.38703 (6)	0.61876 (6)	0.35631 (5)	0.05568 (19)
N1	0.17597 (19)	0.76385 (18)	0.51155 (16)	0.0481 (4)
H1A	0.1340	0.7829	0.5883	0.058*
N2	0.31741 (19)	0.59706 (19)	0.60148 (16)	0.0499 (4)
H2A	0.3850	0.5304	0.5884	0.060*
C1	0.2911 (3)	1.1300 (3)	0.2466 (3)	0.0826 (8)
H1B	0.3984	1.1334	0.2987	0.124*
H1C	0.2584	1.2312	0.2728	0.124*
H1D	0.2915	1.0943	0.1449	0.124*
C2	−0.2810 (3)	0.8645 (4)	0.1871 (3)	0.0815 (8)
H2B	−0.3012	0.9263	0.1251	0.122*
H2C	−0.3452	0.8911	0.2617	0.122*
H2D	−0.3101	0.7576	0.1318	0.122*
C3	0.2287 (2)	0.9438 (2)	0.3790 (2)	0.0477 (4)
H3A	0.3381	0.9609	0.4218	0.057*
C4	0.1728 (2)	1.0214 (2)	0.2835 (2)	0.0513 (5)
C5	0.0072 (2)	0.9943 (2)	0.2225 (2)	0.0507 (5)
H5A	−0.0310	1.0453	0.1584	0.061*
C6	−0.1017 (2)	0.8935 (2)	0.2548 (2)	0.0492 (4)
C7	−0.0428 (2)	0.8165 (2)	0.34959 (19)	0.0452 (4)
H7A	−0.1138	0.7483	0.3724	0.054*
C8	0.1213 (2)	0.84127 (19)	0.40996 (18)	0.0419 (4)
C9	0.2877 (2)	0.6635 (2)	0.49727 (18)	0.0417 (4)
C10	0.2511 (2)	0.6231 (2)	0.73090 (18)	0.0418 (4)
C11	0.3591 (3)	0.6609 (3)	0.8603 (2)	0.0635 (6)
H11A	0.4707	0.6749	0.8619	0.076*
C12	0.3007 (3)	0.6779 (3)	0.9874 (2)	0.0723 (7)
H12A	0.3736	0.7021	1.0740	0.087*
C13	0.1356 (3)	0.6592 (2)	0.9868 (2)	0.0579 (5)
H13A	0.0973	0.6729	1.0728	0.069*
C14	0.0281 (2)	0.6203 (2)	0.8582 (2)	0.0531 (5)
H14A	−0.0833	0.6064	0.8572	0.064*
C15	0.0849 (2)	0.6016 (2)	0.7296 (2)	0.0461 (4)
H15A	0.0117	0.5747	0.6429	0.055*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0619 (3)	0.0785 (4)	0.0472 (3)	0.0398 (3)	0.0248 (2)	0.0356 (2)
N1	0.0564 (9)	0.0570 (9)	0.0464 (8)	0.0294 (7)	0.0211 (7)	0.0282 (7)
N2	0.0534 (9)	0.0676 (10)	0.0466 (8)	0.0331 (8)	0.0205 (7)	0.0327 (7)
C1	0.0739 (16)	0.0851 (17)	0.114 (2)	0.0088 (13)	0.0233 (15)	0.0667 (17)
C2	0.0535 (13)	0.102 (2)	0.0914 (19)	0.0119 (13)	−0.0059 (12)	0.0430 (16)
C3	0.0422 (9)	0.0523 (10)	0.0547 (10)	0.0127 (8)	0.0092 (8)	0.0241 (8)
C4	0.0566 (11)	0.0489 (10)	0.0591 (11)	0.0140 (8)	0.0172 (9)	0.0280 (9)
C5	0.0606 (12)	0.0508 (10)	0.0497 (10)	0.0219 (9)	0.0094 (8)	0.0259 (8)
C6	0.0462 (10)	0.0501 (10)	0.0525 (10)	0.0155 (8)	0.0061 (8)	0.0169 (8)
C7	0.0464 (10)	0.0440 (9)	0.0508 (10)	0.0130 (7)	0.0136 (8)	0.0194 (8)
C8	0.0473 (10)	0.0430 (9)	0.0436 (9)	0.0193 (7)	0.0144 (7)	0.0193 (7)
C9	0.0412 (9)	0.0495 (9)	0.0404 (8)	0.0167 (7)	0.0095 (7)	0.0196 (7)
C10	0.0472 (9)	0.0451 (9)	0.0417 (9)	0.0138 (7)	0.0131 (7)	0.0220 (7)
C11	0.0443 (10)	0.1004 (17)	0.0518 (11)	0.0002 (10)	0.0069 (8)	0.0360 (11)
C12	0.0680 (14)	0.1048 (19)	0.0416 (11)	−0.0103 (13)	0.0039 (10)	0.0279 (11)
C13	0.0745 (14)	0.0600 (12)	0.0488 (11)	0.0094 (10)	0.0270 (10)	0.0236 (9)
C14	0.0512 (11)	0.0538 (11)	0.0683 (13)	0.0142 (8)	0.0252 (9)	0.0313 (9)
C15	0.0456 (10)	0.0492 (10)	0.0482 (10)	0.0111 (7)	0.0084 (7)	0.0212 (8)

Geometric parameters (Å, º)

S1—C9	1.6897 (17)	C4—C5	1.398 (3)
N1—C9	1.356 (2)	C5—C6	1.388 (3)
N1—C8	1.439 (2)	C5—H5A	0.9300
N1—H1A	0.8600	C6—C7	1.393 (2)
N2—C9	1.350 (2)	C7—C8	1.386 (3)
N2—C10	1.432 (2)	C7—H7A	0.9300
N2—H2A	0.8600	C10—C11	1.383 (3)
C1—C4	1.512 (3)	C10—C15	1.388 (3)
C1—H1B	0.9600	C11—C12	1.386 (3)
C1—H1C	0.9600	C11—H11A	0.9300
C1—H1D	0.9600	C12—C13	1.378 (3)
C2—C6	1.518 (3)	C12—H12A	0.9300
C2—H2B	0.9600	C13—C14	1.375 (3)
C2—H2C	0.9600	C13—H13A	0.9300
C2—H2D	0.9600	C14—C15	1.390 (3)
C3—C8	1.384 (3)	C14—H14A	0.9300
C3—C4	1.395 (2)	C15—H15A	0.9300
C3—H3A	0.9300
C9—N1—C8	125.94 (14)	C7—C6—C2	120.04 (19)
C9—N1—H1A	117.0	C8—C7—C6	120.14 (17)
C8—N1—H1A	117.0	C8—C7—H7A	119.9
C9—N2—C10	128.50 (14)	C6—C7—H7A	119.9
C9—N2—H2A	115.8	C3—C8—C7	120.93 (16)
C10—N2—H2A	115.8	C3—C8—N1	120.63 (16)
C4—C1—H1B	109.5	C7—C8—N1	118.36 (16)
C4—C1—H1C	109.5	N2—C9—N1	117.07 (15)
H1B—C1—H1C	109.5	N2—C9—S1	119.88 (12)
C4—C1—H1D	109.5	N1—C9—S1	123.04 (13)
H1B—C1—H1D	109.5	C11—C10—C15	119.58 (17)
H1C—C1—H1D	109.5	C11—C10—N2	117.76 (16)
C6—C2—H2B	109.5	C15—C10—N2	122.50 (16)
C6—C2—H2C	109.5	C10—C11—C12	119.82 (19)
H2B—C2—H2C	109.5	C10—C11—H11A	120.1
C6—C2—H2D	109.5	C12—C11—H11A	120.1
H2B—C2—H2D	109.5	C13—C12—C11	120.8 (2)
H2C—C2—H2D	109.5	C13—C12—H12A	119.6
C8—C3—C4	119.93 (17)	C11—C12—H12A	119.6
C8—C3—H3A	120.0	C14—C13—C12	119.49 (18)
C4—C3—H3A	120.0	C14—C13—H13A	120.3
C3—C4—C5	118.50 (17)	C12—C13—H13A	120.3
C3—C4—C1	119.87 (19)	C13—C14—C15	120.41 (18)
C5—C4—C1	121.63 (18)	C13—C14—H14A	119.8
C6—C5—C4	121.90 (16)	C15—C14—H14A	119.8
C6—C5—H5A	119.1	C10—C15—C14	119.91 (17)
C4—C5—H5A	119.1	C10—C15—H15A	120.0
C5—C6—C7	118.59 (17)	C14—C15—H15A	120.0
C5—C6—C2	121.36 (18)
C8—C3—C4—C5	0.8 (3)	C10—N2—C9—N1	−3.0 (3)
C8—C3—C4—C1	−178.3 (2)	C10—N2—C9—S1	177.62 (15)
C3—C4—C5—C6	0.2 (3)	C8—N1—C9—N2	−176.96 (17)
C1—C4—C5—C6	179.3 (2)	C8—N1—C9—S1	2.4 (3)
C4—C5—C6—C7	−0.7 (3)	C9—N2—C10—C11	−126.3 (2)
C4—C5—C6—C2	−179.7 (2)	C9—N2—C10—C15	58.1 (3)
C5—C6—C7—C8	0.2 (3)	C15—C10—C11—C12	−0.4 (3)
C2—C6—C7—C8	179.1 (2)	N2—C10—C11—C12	−176.1 (2)
C4—C3—C8—C7	−1.3 (3)	C10—C11—C12—C13	−0.8 (4)
C4—C3—C8—N1	−178.10 (17)	C11—C12—C13—C14	1.3 (4)
C6—C7—C8—C3	0.9 (3)	C12—C13—C14—C15	−0.8 (3)
C6—C7—C8—N1	177.69 (16)	C11—C10—C15—C14	0.9 (3)
C9—N1—C8—C3	−63.1 (3)	N2—C10—C15—C14	176.39 (16)
C9—N1—C8—C7	120.0 (2)	C13—C14—C15—C10	−0.4 (3)