The title molecule, C
12H
15ClN
2OS, shows the typical geometric parameters of a substituted thiourea derivative. There is an intramolecular N—H
O hydrogen bond and the crystal packing is characterized by intermolecular N—H
S hydrogen bonds.
Supporting information
CCDC reference: 636744
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.003 Å
- R factor = 0.039
- wR factor = 0.105
- Data-to-parameter ratio = 15.9
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.57 Ratio
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
1 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: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003) and XP in SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: PLATON and SHELXL97.
1-(2-Chlorophenyl)-3-pivaloylthiourea
top
Crystal data top
C12H15ClN2OS | F(000) = 568 |
Mr = 270.77 | Dx = 1.293 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 7381 reflections |
a = 10.7622 (10) Å | θ = 3.8–25.7° |
b = 12.0925 (15) Å | µ = 0.41 mm−1 |
c = 10.9239 (11) Å | T = 173 K |
β = 101.840 (8)° | Block, colourless |
V = 1391.4 (3) Å3 | 0.37 × 0.33 × 0.31 mm |
Z = 4 | |
Data collection top
Stoe IPDS-II two-circle diffractometer | 2598 independent reflections |
Radiation source: fine-focus sealed tube | 2085 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.054 |
ω scans | θmax = 25.6°, θmin = 3.8° |
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995) | h = −11→13 |
Tmin = 0.863, Tmax = 0.883 | k = −14→13 |
8633 measured reflections | l = −13→13 |
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 atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.105 | w = 1/[σ2(Fo2) + (0.0575P)2 + 0.1984P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
2598 reflections | Δρmax = 0.23 e Å−3 |
163 parameters | Δρmin = −0.27 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 (2) |
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 | |
Cl1 | 0.29279 (8) | 0.10408 (6) | 0.42381 (6) | 0.0555 (3) | |
S1 | 0.00137 (5) | 0.33336 (4) | 0.51918 (5) | 0.02659 (18) | |
C1 | 0.33946 (18) | 0.48014 (17) | 0.62725 (17) | 0.0203 (4) | |
O1 | 0.41911 (14) | 0.40828 (13) | 0.66370 (15) | 0.0307 (4) | |
N1 | 0.21295 (15) | 0.45259 (14) | 0.57961 (15) | 0.0199 (4) | |
H1 | 0.157 (3) | 0.513 (2) | 0.545 (2) | 0.049 (8)* | |
C2 | 0.15775 (18) | 0.34847 (16) | 0.57392 (17) | 0.0177 (4) | |
N2 | 0.23505 (17) | 0.26352 (14) | 0.61387 (15) | 0.0211 (4) | |
H2 | 0.314 (3) | 0.283 (2) | 0.635 (2) | 0.047 (8)* | |
C11 | 0.3710 (2) | 0.60335 (17) | 0.63279 (19) | 0.0248 (5) | |
C12 | 0.5140 (2) | 0.6162 (2) | 0.6849 (3) | 0.0457 (7) | |
H12A | 0.5364 | 0.6949 | 0.6891 | 0.069* | |
H12B | 0.5614 | 0.5779 | 0.6299 | 0.069* | |
H12C | 0.5356 | 0.5840 | 0.7689 | 0.069* | |
C13 | 0.3382 (2) | 0.65416 (19) | 0.5002 (2) | 0.0299 (5) | |
H13A | 0.3596 | 0.7330 | 0.5048 | 0.045* | |
H13B | 0.2473 | 0.6451 | 0.4658 | 0.045* | |
H13C | 0.3871 | 0.6166 | 0.4461 | 0.045* | |
C14 | 0.2969 (2) | 0.66189 (19) | 0.7201 (2) | 0.0358 (6) | |
H14A | 0.3178 | 0.7409 | 0.7240 | 0.054* | |
H14B | 0.3201 | 0.6298 | 0.8040 | 0.054* | |
H14C | 0.2056 | 0.6524 | 0.6879 | 0.054* | |
C21 | 0.19072 (19) | 0.15291 (16) | 0.62379 (18) | 0.0211 (4) | |
C22 | 0.2123 (2) | 0.07097 (18) | 0.54181 (19) | 0.0281 (5) | |
C23 | 0.1717 (2) | −0.03649 (19) | 0.5544 (2) | 0.0378 (6) | |
H23 | 0.1880 | −0.0925 | 0.4987 | 0.045* | |
C24 | 0.1076 (2) | −0.06183 (19) | 0.6483 (2) | 0.0366 (6) | |
H24 | 0.0782 | −0.1351 | 0.6559 | 0.044* | |
C25 | 0.0859 (2) | 0.01903 (19) | 0.7313 (2) | 0.0332 (5) | |
H25 | 0.0429 | 0.0009 | 0.7964 | 0.040* | |
C26 | 0.1270 (2) | 0.12637 (18) | 0.71920 (19) | 0.0275 (5) | |
H26 | 0.1118 | 0.1819 | 0.7758 | 0.033* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0915 (6) | 0.0388 (4) | 0.0483 (4) | −0.0045 (4) | 0.0425 (4) | −0.0087 (3) |
S1 | 0.0182 (3) | 0.0151 (3) | 0.0433 (3) | 0.0000 (2) | −0.0009 (2) | −0.0006 (2) |
C1 | 0.0185 (10) | 0.0236 (11) | 0.0187 (10) | −0.0015 (9) | 0.0038 (8) | −0.0006 (8) |
O1 | 0.0184 (7) | 0.0237 (9) | 0.0480 (9) | 0.0010 (7) | 0.0017 (7) | 0.0063 (7) |
N1 | 0.0180 (8) | 0.0150 (9) | 0.0252 (9) | 0.0008 (7) | 0.0012 (7) | 0.0008 (7) |
C2 | 0.0193 (10) | 0.0155 (10) | 0.0189 (9) | 0.0003 (8) | 0.0049 (8) | −0.0012 (8) |
N2 | 0.0179 (9) | 0.0153 (9) | 0.0291 (9) | 0.0016 (7) | 0.0022 (7) | 0.0009 (7) |
C11 | 0.0217 (11) | 0.0203 (11) | 0.0297 (11) | −0.0034 (9) | −0.0010 (9) | 0.0019 (9) |
C12 | 0.0325 (14) | 0.0296 (14) | 0.0649 (17) | −0.0109 (11) | −0.0133 (12) | 0.0059 (12) |
C13 | 0.0277 (12) | 0.0265 (12) | 0.0358 (12) | −0.0034 (10) | 0.0073 (9) | 0.0064 (10) |
C14 | 0.0543 (16) | 0.0223 (12) | 0.0283 (12) | −0.0029 (11) | 0.0027 (11) | −0.0044 (9) |
C21 | 0.0204 (10) | 0.0151 (10) | 0.0255 (10) | 0.0021 (8) | −0.0005 (8) | 0.0024 (8) |
C22 | 0.0349 (12) | 0.0227 (11) | 0.0261 (11) | 0.0011 (10) | 0.0053 (9) | −0.0010 (9) |
C23 | 0.0517 (15) | 0.0188 (12) | 0.0416 (13) | 0.0030 (11) | 0.0065 (11) | −0.0078 (10) |
C24 | 0.0410 (14) | 0.0167 (11) | 0.0488 (14) | −0.0051 (11) | 0.0014 (11) | 0.0062 (10) |
C25 | 0.0351 (13) | 0.0262 (13) | 0.0383 (13) | −0.0020 (10) | 0.0078 (10) | 0.0087 (10) |
C26 | 0.0301 (12) | 0.0230 (11) | 0.0297 (11) | 0.0016 (9) | 0.0068 (9) | 0.0010 (9) |
Geometric parameters (Å, º) top
Cl1—C22 | 1.741 (2) | C13—H13A | 0.9800 |
S1—C2 | 1.676 (2) | C13—H13B | 0.9800 |
C1—O1 | 1.228 (2) | C13—H13C | 0.9800 |
C1—N1 | 1.395 (2) | C14—H14A | 0.9800 |
C1—C11 | 1.527 (3) | C14—H14B | 0.9800 |
N1—C2 | 1.388 (2) | C14—H14C | 0.9800 |
N1—H1 | 0.97 (3) | C21—C22 | 1.387 (3) |
C2—N2 | 1.337 (3) | C21—C26 | 1.398 (3) |
N2—C21 | 1.432 (3) | C22—C23 | 1.386 (3) |
N2—H2 | 0.86 (3) | C23—C24 | 1.384 (3) |
C11—C14 | 1.535 (3) | C23—H23 | 0.9500 |
C11—C12 | 1.536 (3) | C24—C25 | 1.385 (3) |
C11—C13 | 1.546 (3) | C24—H24 | 0.9500 |
C12—H12A | 0.9800 | C25—C26 | 1.386 (3) |
C12—H12B | 0.9800 | C25—H25 | 0.9500 |
C12—H12C | 0.9800 | C26—H26 | 0.9500 |
| | | |
O1—C1—N1 | 121.00 (18) | C11—C13—H13C | 109.5 |
O1—C1—C11 | 122.88 (18) | H13A—C13—H13C | 109.5 |
N1—C1—C11 | 116.11 (17) | H13B—C13—H13C | 109.5 |
C2—N1—C1 | 127.55 (17) | C11—C14—H14A | 109.5 |
C2—N1—H1 | 115.8 (17) | C11—C14—H14B | 109.5 |
C1—N1—H1 | 116.6 (17) | H14A—C14—H14B | 109.5 |
N2—C2—N1 | 116.76 (18) | C11—C14—H14C | 109.5 |
N2—C2—S1 | 122.98 (15) | H14A—C14—H14C | 109.5 |
N1—C2—S1 | 120.26 (15) | H14B—C14—H14C | 109.5 |
C2—N2—C21 | 123.21 (17) | C22—C21—C26 | 119.35 (19) |
C2—N2—H2 | 112.9 (18) | C22—C21—N2 | 121.08 (18) |
C21—N2—H2 | 123.8 (18) | C26—C21—N2 | 119.55 (18) |
C1—C11—C14 | 109.58 (17) | C21—C22—C23 | 120.5 (2) |
C1—C11—C12 | 108.13 (18) | C21—C22—Cl1 | 119.24 (17) |
C14—C11—C12 | 109.38 (19) | C23—C22—Cl1 | 120.21 (17) |
C1—C11—C13 | 110.16 (17) | C24—C23—C22 | 119.7 (2) |
C14—C11—C13 | 110.54 (18) | C24—C23—H23 | 120.1 |
C12—C11—C13 | 109.00 (18) | C22—C23—H23 | 120.1 |
C11—C12—H12A | 109.5 | C23—C24—C25 | 120.4 (2) |
C11—C12—H12B | 109.5 | C23—C24—H24 | 119.8 |
H12A—C12—H12B | 109.5 | C25—C24—H24 | 119.8 |
C11—C12—H12C | 109.5 | C24—C25—C26 | 119.9 (2) |
H12A—C12—H12C | 109.5 | C24—C25—H25 | 120.0 |
H12B—C12—H12C | 109.5 | C26—C25—H25 | 120.0 |
C11—C13—H13A | 109.5 | C25—C26—C21 | 120.1 (2) |
C11—C13—H13B | 109.5 | C25—C26—H26 | 120.0 |
H13A—C13—H13B | 109.5 | C21—C26—H26 | 120.0 |
| | | |
O1—C1—N1—C2 | 4.7 (3) | C2—N2—C21—C26 | −72.6 (3) |
C11—C1—N1—C2 | −174.37 (16) | C26—C21—C22—C23 | −0.4 (3) |
C1—N1—C2—N2 | −3.0 (3) | N2—C21—C22—C23 | 178.3 (2) |
C1—N1—C2—S1 | 176.96 (14) | C26—C21—C22—Cl1 | −179.50 (16) |
N1—C2—N2—C21 | 174.50 (16) | N2—C21—C22—Cl1 | −0.8 (3) |
S1—C2—N2—C21 | −5.4 (3) | C21—C22—C23—C24 | 1.0 (4) |
O1—C1—C11—C14 | −117.0 (2) | Cl1—C22—C23—C24 | −179.85 (18) |
N1—C1—C11—C14 | 62.0 (2) | C22—C23—C24—C25 | −1.3 (4) |
O1—C1—C11—C12 | 2.1 (3) | C23—C24—C25—C26 | 1.0 (4) |
N1—C1—C11—C12 | −178.84 (17) | C24—C25—C26—C21 | −0.3 (3) |
O1—C1—C11—C13 | 121.1 (2) | C22—C21—C26—C25 | 0.0 (3) |
N1—C1—C11—C13 | −59.8 (2) | N2—C21—C26—C25 | −178.7 (2) |
C2—N2—C21—C22 | 108.8 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···S1i | 0.97 (3) | 2.53 (3) | 3.4876 (18) | 172.3 (19) |
N2—H2···O1 | 0.86 (3) | 1.88 (3) | 2.616 (2) | 142 (3) |
Symmetry code: (i) −x, −y+1, −z+1. |