Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807034654/cv2277sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807034654/cv2277Isup2.hkl |
CCDC reference: 653948
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.002 Å
- R factor = 0.033
- wR factor = 0.094
- Data-to-parameter ratio = 17.5
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 3 PLAT230_ALERT_2_C Hirshfeld Test Diff for S1 - C9 .. 5.63 su
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 PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 3
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 2 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 2 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
For the synthesis of the title compound, see: Liu et al. (1994). For details of the pharmacological properties of thiazolone derivatives, see: Mane & Ingle (1983).
A mixture of 4-Ethoxyaniline(13.7 g,0.1 mol), 36% aqueous HCl(10.1 g,0.1 mol) and ammonium thiocyanate(7.6 g,0.1 mol) was refluxed in water(30 ml) for 4 hrs, then a white precipitate was observed and filtered. The solid was recrystallized from water to give the pure product. The pure product was dissolved in water evaporated gradually at room temperature to afford single crystals of (I). (m.p. 450–451 K). 1HNMR(CDCl3)σp.p.m.:7.15(d,2H,J=8.4 Hz),6.92(d,2H,J=8.4 Hz), 4.03(q,2H,CH2), 1.42(t,3H,CH3). MS.(m/z,%).196(M,100),163 (35),154 (70),108 (95),80 (35),60 (25).
The atoms H1X, H2X and H2Y were located in difference Fourier maps and refined isotropically with the N—H bond restraint of 0.86 (2) Å. Methyl H atoms were placed in calculated positions, with C—H = 0.96 Å, and torsion angles were refined to fit the electron density [Uiso(H) = 1.5Ueq(C)]. Other H atoms were placed in calculated positions, with C—H = 0.93 Å, and refined in riding mode, with Uiso(H) = 1.2Ueq(C).
Thiazolone derivatives have potential antimicrobial and antitumour properties (Mane et al., 1983). The title compound, (p-ethoxyphenyl)thiourea (I), is an important intermediate in the synthesis of thiazolone derivatives. In our work, we present its crystal structure.
In (I) (Fig. 1), the benzene ring is twisted out of –N1—C9(=S1)—N2 and –O1—C7—C8 planes by the diherdral angles of 59.19 (3)° and 12.26 (3)°, respectively. In the crystal, the weak intermolecular N—H···S and N—H···O hydrogen bonds link the molecules into three-dimensional hydrogen-bonding network (Table 1, Fig. 2).
For the synthesis of the title compound, see: Liu et al. (1994). For details of the pharmacological properties of thiazolone derivatives, see: Mane & Ingle (1983).
Data collection: SMART (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); 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, 2005); software used to prepare material for publication: SHELXTL.
C9H12N2OS | F(000) = 832 |
Mr = 196.27 | Dx = 1.274 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 3819 reflections |
a = 14.8450 (19) Å | θ = 2.8–28.1° |
b = 8.2482 (11) Å | µ = 0.28 mm−1 |
c = 16.860 (2) Å | T = 293 K |
β = 97.489 (1)° | Prismatic, colourless |
V = 2046.8 (4) Å3 | 0.30 × 0.25 × 0.15 mm |
Z = 8 |
Bruker SMART APEXII CCD area-detector diffractometer | 2313 independent reflections |
Radiation source: fine-focus sealed tube | 2082 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.016 |
φ and ω scans | θmax = 27.5°, θmin = 2.4° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −17→19 |
Tmin = 0.921, Tmax = 0.949 | k = −10→10 |
6278 measured reflections | l = −19→21 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.033 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.094 | w = 1/[σ2(Fo2) + (0.0558P)2 + 0.628P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = 0.001 |
2313 reflections | Δρmax = 0.22 e Å−3 |
132 parameters | Δρmin = −0.20 e Å−3 |
3 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0053 (7) |
C9H12N2OS | V = 2046.8 (4) Å3 |
Mr = 196.27 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 14.8450 (19) Å | µ = 0.28 mm−1 |
b = 8.2482 (11) Å | T = 293 K |
c = 16.860 (2) Å | 0.30 × 0.25 × 0.15 mm |
β = 97.489 (1)° |
Bruker SMART APEXII CCD area-detector diffractometer | 2313 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2082 reflections with I > 2σ(I) |
Tmin = 0.921, Tmax = 0.949 | Rint = 0.016 |
6278 measured reflections |
R[F2 > 2σ(F2)] = 0.033 | 3 restraints |
wR(F2) = 0.094 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | Δρmax = 0.22 e Å−3 |
2313 reflections | Δρmin = −0.20 e Å−3 |
132 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 | 0.60518 (2) | 1.19209 (4) | 0.507891 (19) | 0.04179 (14) | |
O1 | 0.64641 (7) | 0.45160 (12) | 0.19824 (6) | 0.0506 (3) | |
N1 | 0.58619 (7) | 0.92414 (14) | 0.42155 (7) | 0.0415 (3) | |
H1X | 0.5372 (10) | 0.9124 (19) | 0.4426 (9) | 0.047 (4)* | |
N2 | 0.71911 (8) | 1.06437 (17) | 0.41752 (8) | 0.0525 (3) | |
H2X | 0.7399 (11) | 0.9898 (19) | 0.3879 (10) | 0.058 (5)* | |
H2Y | 0.7562 (10) | 1.1336 (19) | 0.4382 (10) | 0.052 (4)* | |
C1 | 0.60403 (8) | 0.80089 (15) | 0.36640 (7) | 0.0365 (3) | |
C2 | 0.61645 (9) | 0.84100 (16) | 0.28852 (8) | 0.0411 (3) | |
H2 | 0.6153 | 0.9492 | 0.2729 | 0.049* | |
C3 | 0.63050 (9) | 0.72167 (16) | 0.23422 (7) | 0.0415 (3) | |
H3 | 0.6393 | 0.7497 | 0.1824 | 0.050* | |
C4 | 0.63154 (9) | 0.56007 (15) | 0.25676 (7) | 0.0387 (3) | |
C5 | 0.61802 (10) | 0.51855 (17) | 0.33402 (8) | 0.0475 (3) | |
H5 | 0.6179 | 0.4102 | 0.3493 | 0.057* | |
C6 | 0.60467 (10) | 0.63975 (17) | 0.38853 (8) | 0.0458 (3) | |
H6 | 0.5961 | 0.6120 | 0.4405 | 0.055* | |
C7 | 0.62819 (11) | 0.28480 (17) | 0.21063 (10) | 0.0515 (4) | |
H7A | 0.5677 | 0.2719 | 0.2256 | 0.062* | |
H7B | 0.6717 | 0.2415 | 0.2533 | 0.062* | |
C8 | 0.63544 (13) | 0.1967 (2) | 0.13409 (10) | 0.0625 (4) | |
H8A | 0.5950 | 0.2450 | 0.0916 | 0.094* | |
H8B | 0.6193 | 0.0849 | 0.1398 | 0.094* | |
H8C | 0.6967 | 0.2035 | 0.1218 | 0.094* | |
C9 | 0.63966 (8) | 1.05019 (15) | 0.44530 (7) | 0.0360 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0422 (2) | 0.0416 (2) | 0.0448 (2) | −0.01078 (12) | 0.01772 (14) | −0.01294 (12) |
O1 | 0.0699 (7) | 0.0407 (5) | 0.0453 (5) | −0.0050 (5) | 0.0236 (5) | −0.0091 (4) |
N1 | 0.0395 (6) | 0.0443 (6) | 0.0442 (6) | −0.0121 (5) | 0.0187 (5) | −0.0130 (5) |
N2 | 0.0418 (6) | 0.0594 (8) | 0.0607 (7) | −0.0188 (6) | 0.0236 (5) | −0.0276 (6) |
C1 | 0.0340 (6) | 0.0407 (6) | 0.0359 (6) | −0.0081 (5) | 0.0090 (5) | −0.0083 (5) |
C2 | 0.0492 (7) | 0.0360 (6) | 0.0389 (6) | −0.0021 (5) | 0.0085 (5) | −0.0001 (5) |
C3 | 0.0510 (7) | 0.0435 (7) | 0.0309 (6) | −0.0015 (5) | 0.0096 (5) | 0.0005 (5) |
C4 | 0.0412 (6) | 0.0394 (6) | 0.0369 (6) | −0.0037 (5) | 0.0105 (5) | −0.0062 (5) |
C5 | 0.0652 (9) | 0.0365 (7) | 0.0434 (7) | −0.0064 (6) | 0.0165 (6) | 0.0000 (5) |
C6 | 0.0595 (8) | 0.0458 (7) | 0.0349 (6) | −0.0098 (6) | 0.0159 (6) | −0.0013 (5) |
C7 | 0.0559 (8) | 0.0419 (7) | 0.0601 (9) | −0.0089 (6) | 0.0204 (7) | −0.0099 (6) |
C8 | 0.0717 (11) | 0.0540 (9) | 0.0624 (10) | −0.0081 (8) | 0.0116 (8) | −0.0210 (7) |
C9 | 0.0368 (6) | 0.0392 (6) | 0.0334 (6) | −0.0065 (5) | 0.0096 (4) | −0.0037 (5) |
S1—C9 | 1.6989 (12) | C3—C4 | 1.3855 (18) |
O1—C4 | 1.3708 (15) | C3—H3 | 0.9300 |
O1—C7 | 1.4228 (17) | C4—C5 | 1.3866 (18) |
N1—C9 | 1.3374 (16) | C5—C6 | 1.3894 (19) |
N1—C1 | 1.4255 (15) | C5—H5 | 0.9300 |
N1—H1X | 0.855 (13) | C6—H6 | 0.9300 |
N2—C9 | 1.3297 (16) | C7—C8 | 1.497 (2) |
N2—H2X | 0.874 (14) | C7—H7A | 0.9700 |
N2—H2Y | 0.836 (14) | C7—H7B | 0.9700 |
C1—C6 | 1.3802 (19) | C8—H8A | 0.9599 |
C1—C2 | 1.3895 (18) | C8—H8B | 0.9599 |
C2—C3 | 1.3785 (18) | C8—H8C | 0.9599 |
C2—H2 | 0.9300 | ||
C4—O1—C7 | 118.29 (10) | C4—C5—H5 | 120.2 |
C9—N1—C1 | 126.59 (10) | C6—C5—H5 | 120.2 |
C9—N1—H1X | 117.9 (11) | C1—C6—C5 | 120.71 (12) |
C1—N1—H1X | 115.5 (11) | C1—C6—H6 | 119.6 |
C9—N2—H2X | 122.4 (11) | C5—C6—H6 | 119.6 |
C9—N2—H2Y | 118.6 (11) | O1—C7—C8 | 107.86 (13) |
H2X—N2—H2Y | 117.1 (16) | O1—C7—H7A | 110.1 |
C6—C1—C2 | 119.18 (11) | C8—C7—H7A | 110.1 |
C6—C1—N1 | 120.38 (11) | O1—C7—H7B | 110.1 |
C2—C1—N1 | 120.36 (11) | C8—C7—H7B | 110.1 |
C3—C2—C1 | 120.52 (12) | H7A—C7—H7B | 108.4 |
C3—C2—H2 | 119.7 | C7—C8—H8A | 109.5 |
C1—C2—H2 | 119.7 | C7—C8—H8B | 109.5 |
C2—C3—C4 | 120.13 (11) | H8A—C8—H8B | 109.5 |
C2—C3—H3 | 119.9 | C7—C8—H8C | 109.5 |
C4—C3—H3 | 119.9 | H8A—C8—H8C | 109.5 |
O1—C4—C3 | 115.32 (11) | H8B—C8—H8C | 109.5 |
O1—C4—C5 | 124.86 (12) | N2—C9—N1 | 118.82 (11) |
C3—C4—C5 | 119.83 (12) | N2—C9—S1 | 120.74 (10) |
C4—C5—C6 | 119.62 (12) | N1—C9—S1 | 120.42 (9) |
C9—N1—C1—C6 | 123.61 (15) | O1—C4—C5—C6 | 179.21 (13) |
C9—N1—C1—C2 | −59.64 (19) | C3—C4—C5—C6 | −0.8 (2) |
C6—C1—C2—C3 | −0.9 (2) | C2—C1—C6—C5 | 0.4 (2) |
N1—C1—C2—C3 | −177.68 (12) | N1—C1—C6—C5 | 177.14 (13) |
C1—C2—C3—C4 | 0.6 (2) | C4—C5—C6—C1 | 0.5 (2) |
C7—O1—C4—C3 | −165.98 (13) | C4—O1—C7—C8 | 171.20 (13) |
C7—O1—C4—C5 | 14.0 (2) | C1—N1—C9—N2 | −1.7 (2) |
C2—C3—C4—O1 | −179.75 (12) | C1—N1—C9—S1 | 176.65 (10) |
C2—C3—C4—C5 | 0.3 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1X···S1i | 0.86 (1) | 2.52 (1) | 3.3594 (11) | 166 (1) |
N2—H2X···O1ii | 0.87 (1) | 2.39 (2) | 3.1105 (15) | 141 (1) |
N2—H2Y···S1iii | 0.84 (1) | 2.58 (1) | 3.4008 (13) | 168 (2) |
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x+3/2, y+1/2, −z+1/2; (iii) −x+3/2, −y+5/2, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C9H12N2OS |
Mr | 196.27 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 293 |
a, b, c (Å) | 14.8450 (19), 8.2482 (11), 16.860 (2) |
β (°) | 97.489 (1) |
V (Å3) | 2046.8 (4) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.28 |
Crystal size (mm) | 0.30 × 0.25 × 0.15 |
Data collection | |
Diffractometer | Bruker SMART APEXII CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.921, 0.949 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6278, 2313, 2082 |
Rint | 0.016 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.033, 0.094, 1.06 |
No. of reflections | 2313 |
No. of parameters | 132 |
No. of restraints | 3 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.22, −0.20 |
Computer programs: SMART (Bruker, 2005), SAINT (Bruker, 2005), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2005), SHELXTL.
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1X···S1i | 0.855 (13) | 2.523 (14) | 3.3594 (11) | 166.0 (14) |
N2—H2X···O1ii | 0.874 (14) | 2.386 (16) | 3.1105 (15) | 140.5 (14) |
N2—H2Y···S1iii | 0.836 (14) | 2.578 (14) | 3.4008 (13) | 168.3 (15) |
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x+3/2, y+1/2, −z+1/2; (iii) −x+3/2, −y+5/2, −z+1. |
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Thiazolone derivatives have potential antimicrobial and antitumour properties (Mane et al., 1983). The title compound, (p-ethoxyphenyl)thiourea (I), is an important intermediate in the synthesis of thiazolone derivatives. In our work, we present its crystal structure.
In (I) (Fig. 1), the benzene ring is twisted out of –N1—C9(=S1)—N2 and –O1—C7—C8 planes by the diherdral angles of 59.19 (3)° and 12.26 (3)°, respectively. In the crystal, the weak intermolecular N—H···S and N—H···O hydrogen bonds link the molecules into three-dimensional hydrogen-bonding network (Table 1, Fig. 2).