The molecule of the title compound, C17H18N2O2S, is not planar; the thiourea mean plane is twisted with respect to the benzene rings with dihedral angles of 65.95 (12) and 51.54 (10)°.
Supporting information
CCDC reference: 618347
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.004 Å
- R factor = 0.039
- wR factor = 0.115
- Data-to-parameter ratio = 14.7
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for C1 - C2 .. 7.07 su
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
0 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 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
0 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: SHELXTL (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
1-(4-Ethoxybenzoyl)-3-
o-tolylthiourea
top
Crystal data top
C17H18N2O2S | Z = 2 |
Mr = 314.39 | F(000) = 332 |
Triclinic, P1 | Dx = 1.277 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.734 (1) Å | Cell parameters from 30 reflections |
b = 10.198 (2) Å | θ = 5.1–17.9° |
c = 12.314 (2) Å | µ = 0.21 mm−1 |
α = 103.94 (1)° | T = 296 K |
β = 103.09 (1)° | Block, colorless |
γ = 112.03 (1)° | 0.58 × 0.44 × 0.24 mm |
V = 817.9 (3) Å3 | |
Data collection top
Siemens P4 diffractometer | 2260 reflections with I > 2σ(I) |
Radiation source: normal-focus sealed tube | Rint = 0.010 |
Graphite monochromator | θmax = 25.5°, θmin = 1.8° |
ω scans | h = 0→9 |
Absorption correction: multi-scan (SADABS; Bruker, 1998) | k = −11→10 |
Tmin = 0.880, Tmax = 0.953 | l = −14→14 |
3332 measured reflections | 3 standard reflections every 97 reflections |
2975 independent reflections | intensity decay: 3.4% |
Refinement top
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)] = 0.039 | H-atom parameters constrained |
wR(F2) = 0.115 | w = 1/[σ2(Fo2) + (0.0626P)2 + 0.0506P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max < 0.001 |
2975 reflections | Δρmax = 0.38 e Å−3 |
202 parameters | Δρmin = −0.18 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.019 (4) |
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 | x | y | z | Uiso*/Ueq | |
S | 1.02528 (7) | 0.57617 (6) | 0.35405 (4) | 0.0561 (2) | |
O1 | 0.3909 (2) | 0.21182 (19) | 0.21506 (13) | 0.0798 (5) | |
O2 | 0.2471 (2) | 0.05283 (15) | 0.66329 (12) | 0.0619 (4) | |
N1 | 0.6652 (2) | 0.4382 (2) | 0.18624 (14) | 0.0577 (5) | |
H1 | 0.5403 | 0.3785 | 0.1648 | 0.069* | |
N2 | 0.6851 (2) | 0.39064 (17) | 0.36085 (13) | 0.0476 (4) | |
H2 | 0.7506 | 0.4242 | 0.4362 | 0.057* | |
C1 | 0.6324 (4) | 0.2338 (3) | −0.0313 (2) | 0.0945 (9) | |
H1A | 0.6546 | 0.1880 | −0.1012 | 0.113* | |
H1B | 0.4921 | 0.1893 | −0.0451 | 0.113* | |
H1C | 0.7003 | 0.2169 | 0.0354 | 0.113* | |
C2 | 0.7107 (3) | 0.4008 (3) | −0.00489 (19) | 0.0677 (6) | |
C3 | 0.7688 (4) | 0.4627 (4) | −0.0864 (2) | 0.0877 (9) | |
H3 | 0.7607 | 0.3991 | −0.1577 | 0.105* | |
C4 | 0.8371 (4) | 0.6125 (5) | −0.0665 (3) | 0.0976 (11) | |
H4 | 0.8740 | 0.6501 | −0.1237 | 0.117* | |
C5 | 0.8520 (4) | 0.7093 (4) | 0.0388 (3) | 0.0901 (9) | |
H5 | 0.8979 | 0.8123 | 0.0525 | 0.108* | |
C6 | 0.7983 (4) | 0.6525 (3) | 0.1243 (2) | 0.0714 (7) | |
H6 | 0.8087 | 0.7169 | 0.1960 | 0.086* | |
C7 | 0.7298 (3) | 0.5004 (3) | 0.10164 (17) | 0.0567 (5) | |
C8 | 0.7810 (3) | 0.4646 (2) | 0.29470 (15) | 0.0445 (4) | |
C9 | 0.4971 (3) | 0.2697 (2) | 0.32023 (18) | 0.0525 (5) | |
C10 | 0.4354 (3) | 0.2144 (2) | 0.41251 (17) | 0.0471 (5) | |
C11 | 0.4844 (3) | 0.3098 (2) | 0.52767 (17) | 0.0493 (5) | |
H11 | 0.5643 | 0.4134 | 0.5506 | 0.059* | |
C12 | 0.4162 (3) | 0.2530 (2) | 0.60860 (18) | 0.0520 (5) | |
H12 | 0.4461 | 0.3185 | 0.6849 | 0.062* | |
C13 | 0.3024 (3) | 0.0978 (2) | 0.57635 (18) | 0.0497 (5) | |
C14 | 0.2526 (3) | 0.0008 (2) | 0.46141 (19) | 0.0543 (5) | |
H14 | 0.1762 | −0.1031 | 0.4394 | 0.065* | |
C15 | 0.3168 (3) | 0.0593 (2) | 0.38008 (18) | 0.0540 (5) | |
H15 | 0.2804 | −0.0055 | 0.3024 | 0.065* | |
C16 | 0.1374 (3) | −0.1066 (2) | 0.6371 (2) | 0.0612 (6) | |
H16A | 0.2095 | −0.1593 | 0.6090 | 0.073* | |
H16B | 0.0084 | −0.1475 | 0.5751 | 0.073* | |
C17 | 0.1111 (4) | −0.1278 (3) | 0.7493 (2) | 0.0842 (8) | |
H17A | 0.2390 | −0.0950 | 0.8078 | 0.101* | |
H17B | 0.0288 | −0.2331 | 0.7324 | 0.101* | |
H17C | 0.0488 | −0.0690 | 0.7796 | 0.101* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S | 0.0466 (3) | 0.0593 (3) | 0.0472 (3) | 0.0080 (2) | 0.0108 (2) | 0.0260 (2) |
O1 | 0.0539 (9) | 0.0928 (12) | 0.0546 (9) | −0.0004 (8) | 0.0036 (8) | 0.0344 (8) |
O2 | 0.0678 (10) | 0.0558 (8) | 0.0612 (9) | 0.0176 (7) | 0.0268 (7) | 0.0327 (7) |
N1 | 0.0438 (9) | 0.0764 (12) | 0.0469 (9) | 0.0164 (9) | 0.0134 (7) | 0.0326 (8) |
N2 | 0.0437 (9) | 0.0513 (9) | 0.0399 (8) | 0.0127 (7) | 0.0117 (7) | 0.0209 (7) |
C1 | 0.0803 (19) | 0.115 (2) | 0.0658 (16) | 0.0397 (18) | 0.0163 (14) | 0.0121 (15) |
C2 | 0.0488 (13) | 0.1070 (19) | 0.0482 (12) | 0.0364 (13) | 0.0131 (10) | 0.0313 (12) |
C3 | 0.0639 (16) | 0.162 (3) | 0.0519 (14) | 0.0556 (19) | 0.0250 (12) | 0.0520 (17) |
C4 | 0.0725 (18) | 0.189 (4) | 0.082 (2) | 0.070 (2) | 0.0440 (15) | 0.098 (2) |
C5 | 0.0776 (18) | 0.123 (2) | 0.112 (2) | 0.0518 (18) | 0.0473 (17) | 0.088 (2) |
C6 | 0.0715 (15) | 0.0922 (18) | 0.0724 (15) | 0.0396 (14) | 0.0363 (13) | 0.0511 (14) |
C7 | 0.0439 (11) | 0.0873 (16) | 0.0477 (12) | 0.0293 (11) | 0.0173 (9) | 0.0386 (11) |
C8 | 0.0478 (11) | 0.0459 (10) | 0.0394 (10) | 0.0190 (9) | 0.0151 (8) | 0.0184 (8) |
C9 | 0.0427 (11) | 0.0578 (12) | 0.0525 (12) | 0.0174 (9) | 0.0126 (9) | 0.0253 (10) |
C10 | 0.0372 (10) | 0.0528 (11) | 0.0538 (11) | 0.0176 (9) | 0.0157 (8) | 0.0280 (9) |
C11 | 0.0421 (10) | 0.0441 (10) | 0.0581 (12) | 0.0144 (9) | 0.0159 (9) | 0.0226 (9) |
C12 | 0.0498 (11) | 0.0499 (11) | 0.0525 (11) | 0.0170 (9) | 0.0177 (9) | 0.0218 (9) |
C13 | 0.0434 (11) | 0.0553 (12) | 0.0572 (12) | 0.0222 (9) | 0.0187 (9) | 0.0308 (10) |
C14 | 0.0508 (11) | 0.0442 (10) | 0.0645 (13) | 0.0153 (9) | 0.0196 (10) | 0.0252 (10) |
C15 | 0.0495 (12) | 0.0535 (12) | 0.0516 (11) | 0.0176 (10) | 0.0154 (9) | 0.0184 (9) |
C16 | 0.0600 (13) | 0.0570 (13) | 0.0802 (15) | 0.0257 (11) | 0.0314 (11) | 0.0420 (11) |
C17 | 0.0909 (19) | 0.0793 (17) | 0.0917 (19) | 0.0289 (15) | 0.0401 (16) | 0.0548 (15) |
Geometric parameters (Å, º) top
S—C8 | 1.6612 (19) | C5—H5 | 0.9300 |
O1—C9 | 1.219 (2) | C6—C7 | 1.368 (3) |
O2—C13 | 1.355 (2) | C6—H6 | 0.9300 |
O2—C16 | 1.434 (2) | C9—C10 | 1.480 (3) |
N1—C8 | 1.328 (2) | C10—C11 | 1.384 (3) |
N1—C7 | 1.433 (2) | C10—C15 | 1.394 (3) |
N1—H1 | 0.8600 | C11—C12 | 1.376 (2) |
N2—C9 | 1.383 (2) | C11—H11 | 0.9300 |
N2—C8 | 1.390 (2) | C12—C13 | 1.390 (3) |
N2—H2 | 0.8600 | C12—H12 | 0.9300 |
C1—C2 | 1.498 (4) | C13—C14 | 1.386 (3) |
C1—H1A | 0.9600 | C14—C15 | 1.377 (3) |
C1—H1B | 0.9600 | C14—H14 | 0.9300 |
C1—H1C | 0.9600 | C15—H15 | 0.9300 |
C2—C3 | 1.380 (3) | C16—C17 | 1.495 (3) |
C2—C7 | 1.390 (3) | C16—H16A | 0.9700 |
C3—C4 | 1.352 (4) | C16—H16B | 0.9700 |
C3—H3 | 0.9300 | C17—H17A | 0.9600 |
C4—C5 | 1.378 (4) | C17—H17B | 0.9600 |
C4—H4 | 0.9300 | C17—H17C | 0.9600 |
C5—C6 | 1.389 (3) | | |
| | | |
C13—O2—C16 | 118.05 (16) | O1—C9—N2 | 121.99 (18) |
C8—N1—C7 | 125.80 (16) | O1—C9—C10 | 122.47 (18) |
C8—N1—H1 | 117.1 | N2—C9—C10 | 115.53 (16) |
C7—N1—H1 | 117.1 | C11—C10—C15 | 118.80 (17) |
C9—N2—C8 | 127.92 (15) | C11—C10—C9 | 123.08 (17) |
C9—N2—H2 | 116.0 | C15—C10—C9 | 118.08 (18) |
C8—N2—H2 | 116.0 | C12—C11—C10 | 120.72 (18) |
C2—C1—H1A | 109.5 | C12—C11—H11 | 119.6 |
C2—C1—H1B | 109.5 | C10—C11—H11 | 119.6 |
H1A—C1—H1B | 109.5 | C11—C12—C13 | 119.99 (19) |
C2—C1—H1C | 109.5 | C11—C12—H12 | 120.0 |
H1A—C1—H1C | 109.5 | C13—C12—H12 | 120.0 |
H1B—C1—H1C | 109.5 | O2—C13—C14 | 124.61 (18) |
C3—C2—C7 | 116.9 (3) | O2—C13—C12 | 115.50 (18) |
C3—C2—C1 | 120.7 (3) | C14—C13—C12 | 119.90 (17) |
C7—C2—C1 | 122.3 (2) | C15—C14—C13 | 119.59 (18) |
C4—C3—C2 | 122.4 (3) | C15—C14—H14 | 120.2 |
C4—C3—H3 | 118.8 | C13—C14—H14 | 120.2 |
C2—C3—H3 | 118.8 | C14—C15—C10 | 120.94 (19) |
C3—C4—C5 | 119.9 (2) | C14—C15—H15 | 119.5 |
C3—C4—H4 | 120.0 | C10—C15—H15 | 119.5 |
C5—C4—H4 | 120.0 | O2—C16—C17 | 107.94 (19) |
C4—C5—C6 | 119.7 (3) | O2—C16—H16A | 110.1 |
C4—C5—H5 | 120.1 | C17—C16—H16A | 110.1 |
C6—C5—H5 | 120.1 | O2—C16—H16B | 110.1 |
C7—C6—C5 | 119.0 (3) | C17—C16—H16B | 110.1 |
C7—C6—H6 | 120.5 | H16A—C16—H16B | 108.4 |
C5—C6—H6 | 120.5 | C16—C17—H17A | 109.5 |
C6—C7—C2 | 122.0 (2) | C16—C17—H17B | 109.5 |
C6—C7—N1 | 120.0 (2) | H17A—C17—H17B | 109.5 |
C2—C7—N1 | 117.9 (2) | C16—C17—H17C | 109.5 |
N1—C8—N2 | 115.61 (16) | H17A—C17—H17C | 109.5 |
N1—C8—S | 125.12 (14) | H17B—C17—H17C | 109.5 |
N2—C8—S | 119.27 (13) | | |
| | | |
C7—C2—C3—C4 | −1.5 (3) | C8—N2—C9—C10 | 179.73 (17) |
C1—C2—C3—C4 | 178.9 (2) | O1—C9—C10—C11 | −143.9 (2) |
C2—C3—C4—C5 | 0.5 (4) | N2—C9—C10—C11 | 37.0 (3) |
C3—C4—C5—C6 | 0.5 (4) | O1—C9—C10—C15 | 33.9 (3) |
C4—C5—C6—C7 | −0.5 (4) | N2—C9—C10—C15 | −145.28 (18) |
C5—C6—C7—C2 | −0.6 (3) | C15—C10—C11—C12 | −0.5 (3) |
C5—C6—C7—N1 | −177.2 (2) | C9—C10—C11—C12 | 177.26 (18) |
C3—C2—C7—C6 | 1.6 (3) | C10—C11—C12—C13 | 2.2 (3) |
C1—C2—C7—C6 | −178.9 (2) | C16—O2—C13—C14 | 3.2 (3) |
C3—C2—C7—N1 | 178.30 (18) | C16—O2—C13—C12 | −177.16 (17) |
C1—C2—C7—N1 | −2.2 (3) | C11—C12—C13—O2 | 178.26 (17) |
C8—N1—C7—C6 | −67.5 (3) | C11—C12—C13—C14 | −2.1 (3) |
C8—N1—C7—C2 | 115.7 (2) | O2—C13—C14—C15 | 179.79 (18) |
C7—N1—C8—N2 | −179.55 (18) | C12—C13—C14—C15 | 0.2 (3) |
C7—N1—C8—S | 0.2 (3) | C13—C14—C15—C10 | 1.6 (3) |
C9—N2—C8—N1 | 15.5 (3) | C11—C10—C15—C14 | −1.5 (3) |
C9—N2—C8—S | −164.23 (16) | C9—C10—C15—C14 | −179.31 (18) |
C8—N2—C9—O1 | 0.6 (3) | C13—O2—C16—C17 | 174.69 (18) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1 | 0.86 | 1.99 | 2.649 (2) | 133 |
N2—H2···Si | 0.86 | 2.77 | 3.5712 (16) | 156 |
Symmetry code: (i) −x+2, −y+1, −z+1. |