organic compounds
Molecules of the title compound, C14H18N2O4S, are linked into a linear chain, which propagates along the a axis of the triclinic unit cell through intermolecular hydrogen bonding between the carboxyl group and the thioxo S atom.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806013146/nc2011sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806013146/nc2011Isup2.hkl |
CCDC reference: 608462
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.004 Å
- Disorder in main residue
- R factor = 0.062
- wR factor = 0.162
- Data-to-parameter ratio = 14.5
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O4 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C5 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C11 PLAT301_ALERT_3_C Main Residue Disorder ......................... 16.00 Perc. PLAT414_ALERT_2_C Short Intra D-H..H-X H1N .. H2 .. 1.95 Ang. PLAT414_ALERT_2_C Short Intra D-H..H-X H1N .. H2' .. 1.99 Ang. PLAT420_ALERT_2_C D-H Without Acceptor N1 - H1N ... ? PLAT731_ALERT_1_C Bond Calc 0.86(3), Rep 0.850(10) ...... 3.00 su-Rat O1 -H1O 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.86(3), Rep 0.850(10) ...... 3.00 su-Rat O1 -H1O 1.555 1.555
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 10 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 6 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion
Computing details top
Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); 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, 1998); software used to prepare material for publication: SHELXL97.
2-[3-(4-Methoxybenzoyl)thioureido]-3-methylbutyric acid top
Crystal data top
C14H18N2O4S | Z = 2 |
Mr = 310.36 | F(000) = 328 |
Triclinic, P1 | Dx = 1.332 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.051 (1) Å | Cell parameters from 679 reflections |
b = 8.084 (1) Å | θ = 1.6–22.2° |
c = 13.205 (2) Å | µ = 0.23 mm−1 |
α = 83.741 (2)° | T = 295 K |
β = 80.164 (3)° | Block, colourless |
γ = 66.162 (2)° | 0.31 × 0.16 × 0.12 mm |
V = 773.8 (2) Å3 |
Data collection top
Bruker APEX area-detector diffractometer | 2078 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.034 |
Graphite monochromator | θmax = 27.5°, θmin = 1.6° |
φ and ω scans | h = −10→10 |
8876 measured reflections | k = −10→10 |
3509 independent reflections | l = −17→17 |
Refinement top
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)] = 0.062 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.162 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0853P)2] where P = (Fo2 + 2Fc2)/3 |
3509 reflections | (Δ/σ)max = 0.001 |
242 parameters | Δρmax = 0.29 e Å−3 |
26 restraints | Δρmin = −0.15 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | Occ. (<1) | |
S1 | 0.4504 (1) | 0.48898 (9) | 0.87273 (5) | 0.0644 (3) | |
O1 | 0.3998 (3) | −0.1208 (2) | 0.9046 (2) | 0.083 (1) | |
O2 | 0.3324 (3) | −0.0243 (2) | 0.7472 (2) | 0.073 (1) | |
O3 | 0.2455 (3) | 0.4241 (2) | 0.5866 (1) | 0.067 (1) | |
O4 | 0.1847 (4) | 1.1160 (3) | 0.2984 (2) | 0.092 (1) | |
N1 | 0.3413 (3) | 0.5650 (3) | 0.6893 (2) | 0.055 (1) | |
N2 | 0.3243 (3) | 0.3060 (3) | 0.7749 (2) | 0.049 (1) | |
C1 | 0.2619 (3) | 0.7037 (3) | 0.5225 (2) | 0.048 (1) | |
C4 | 0.2144 (4) | 0.9845 (3) | 0.3740 (2) | 0.061 (1) | |
C2' | 0.256 (2) | 0.870 (1) | 0.5441 (9) | 0.047 (2) | 0.42 (2) |
C3' | 0.232 (2) | 1.013 (2) | 0.4720 (7) | 0.042 (2) | 0.42 (2) |
C5' | 0.221 (2) | 0.819 (1) | 0.3471 (9) | 0.061 (3) | 0.42 (2) |
C6' | 0.244 (2) | 0.683 (2) | 0.4221 (6) | 0.049 (2) | 0.42 (2) |
C2 | 0.324 (2) | 0.837 (1) | 0.5308 (7) | 0.056 (2) | 0.58 (2) |
C3 | 0.300 (2) | 0.977 (1) | 0.4570 (6) | 0.053 (2) | 0.58 (2) |
C5 | 0.151 (2) | 0.851 (1) | 0.3668 (8) | 0.090 (3) | 0.58 (2) |
C6 | 0.174 (2) | 0.711 (1) | 0.4385 (7) | 0.068 (2) | 0.58 (2) |
C7 | 0.2051 (5) | 1.2756 (4) | 0.3142 (2) | 0.082 (1) | |
C8 | 0.2814 (3) | 0.5513 (3) | 0.5990 (2) | 0.050 (1) | |
C9 | 0.3670 (3) | 0.4472 (3) | 0.7752 (2) | 0.048 (1) | |
C10 | 0.3217 (3) | 0.1865 (3) | 0.8658 (2) | 0.046 (1) | |
C11 | 0.1394 (4) | 0.2697 (3) | 0.9371 (2) | 0.054 (1) | |
C12 | −0.0224 (4) | 0.2735 (5) | 0.8913 (2) | 0.083 (1) | |
C13 | 0.1460 (5) | 0.1833 (4) | 1.0451 (2) | 0.085 (1) | |
C14 | 0.3521 (4) | 0.0039 (3) | 0.8307 (2) | 0.055 (1) | |
H1o | 0.400 (5) | −0.220 (3) | 0.887 (2) | 0.10 (1)* | |
H1n | 0.361 (3) | 0.658 (2) | 0.696 (2) | 0.05 (1)* | |
H2n | 0.292 (3) | 0.281 (3) | 0.722 (1) | 0.06 (1)* | |
H2' | 0.2675 | 0.8867 | 0.6106 | 0.056* | 0.42 (2) |
H3' | 0.2290 | 1.1226 | 0.4890 | 0.051* | 0.42 (2) |
H5' | 0.2098 | 0.8021 | 0.2804 | 0.073* | 0.42 (2) |
H6' | 0.2469 | 0.5728 | 0.4053 | 0.059* | 0.42 (2) |
H2 | 0.3827 | 0.8331 | 0.5865 | 0.067* | 0.58 (2) |
H3 | 0.3417 | 1.0670 | 0.4636 | 0.063* | 0.58 (2) |
H5 | 0.0912 | 0.8561 | 0.3115 | 0.108* | 0.58 (2) |
H6 | 0.1319 | 0.6220 | 0.4316 | 0.082* | 0.58 (2) |
H7a | 0.1851 | 1.3536 | 0.2533 | 0.123* | |
H7b | 0.3267 | 1.2459 | 0.3291 | 0.123* | |
H7c | 0.1173 | 1.3363 | 0.3710 | 0.123* | |
H10 | 0.4224 | 0.1728 | 0.9028 | 0.056* | |
H11 | 0.1189 | 0.3963 | 0.9437 | 0.064* | |
H12a | −0.1344 | 0.3510 | 0.9299 | 0.124* | |
H12b | −0.0195 | 0.1532 | 0.8939 | 0.124* | |
H12c | −0.0157 | 0.3186 | 0.8211 | 0.124* | |
H13a | 0.2445 | 0.1914 | 1.0734 | 0.127* | |
H13b | 0.1658 | 0.0583 | 1.0427 | 0.127* | |
H13c | 0.0320 | 0.2454 | 1.0875 | 0.127* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0977 (6) | 0.0473 (4) | 0.0649 (5) | −0.0397 (4) | −0.0344 (4) | 0.0109 (3) |
O1 | 0.143 (2) | 0.041 (1) | 0.075 (1) | −0.039 (1) | −0.041 (1) | 0.008 (1) |
O2 | 0.112 (2) | 0.054 (1) | 0.061 (1) | −0.036 (1) | −0.023 (1) | −0.010 (1) |
O3 | 0.098 (2) | 0.057 (1) | 0.058 (1) | −0.038 (1) | −0.023 (1) | 0.002 (1) |
O4 | 0.157 (2) | 0.079 (1) | 0.057 (1) | −0.060 (2) | −0.039 (1) | 0.022 (1) |
N1 | 0.074 (2) | 0.052 (1) | 0.051 (1) | −0.035 (1) | −0.018 (1) | 0.009 (1) |
N2 | 0.068 (1) | 0.043 (1) | 0.041 (1) | −0.028 (1) | −0.010 (1) | −0.001 (1) |
C1 | 0.052 (2) | 0.050 (1) | 0.039 (1) | −0.017 (1) | −0.004 (1) | −0.004 (1) |
C4 | 0.084 (2) | 0.061 (2) | 0.040 (1) | −0.030 (2) | −0.011 (1) | 0.0049 (12) |
C2' | 0.040 (5) | 0.054 (4) | 0.046 (4) | −0.016 (4) | −0.013 (4) | −0.004 (3) |
C3' | 0.028 (5) | 0.040 (4) | 0.055 (5) | −0.009 (4) | 0.000 (4) | −0.007 (3) |
C5' | 0.083 (7) | 0.062 (5) | 0.042 (5) | −0.032 (5) | −0.003 (5) | −0.012 (4) |
C6' | 0.052 (6) | 0.047 (4) | 0.047 (5) | −0.020 (4) | 0.003 (4) | −0.013 (3) |
C2 | 0.056 (5) | 0.071 (4) | 0.047 (4) | −0.030 (4) | −0.019 (4) | 0.013 (3) |
C3 | 0.049 (5) | 0.058 (4) | 0.051 (3) | −0.023 (4) | −0.004 (3) | 0.002 (3) |
C5 | 0.165 (9) | 0.088 (6) | 0.041 (5) | −0.066 (6) | −0.044 (6) | 0.010 (4) |
C6 | 0.099 (7) | 0.066 (5) | 0.053 (4) | −0.042 (5) | −0.020 (4) | 0.000 (3) |
C7 | 0.107 (3) | 0.064 (2) | 0.069 (2) | −0.034 (2) | −0.010 (2) | 0.016 (2) |
C8 | 0.052 (2) | 0.052 (1) | 0.046 (1) | −0.021 (1) | −0.002 (1) | −0.002 (1) |
C9 | 0.051 (1) | 0.043 (1) | 0.049 (1) | −0.019 (1) | −0.005 (1) | 0.002 (1) |
C10 | 0.061 (2) | 0.037 (1) | 0.046 (1) | −0.022 (1) | −0.012 (1) | 0.002 (1) |
C11 | 0.066 (2) | 0.046 (1) | 0.052 (2) | −0.025 (1) | −0.005 (1) | −0.001 (1) |
C12 | 0.068 (2) | 0.096 (2) | 0.086 (2) | −0.035 (2) | −0.009 (2) | 0.001 (2) |
C13 | 0.105 (3) | 0.091 (2) | 0.055 (2) | −0.041 (2) | −0.002 (2) | 0.007 (2) |
C14 | 0.068 (2) | 0.042 (1) | 0.059 (2) | −0.024 (1) | −0.015 (1) | 0.000 (1) |
Geometric parameters (Å, º) top
S1—C9 | 1.672 (3) | C11—C12 | 1.515 (4) |
O1—C14 | 1.310 (3) | C11—C13 | 1.517 (3) |
O2—C14 | 1.198 (3) | O1—H1o | 0.85 (1) |
O3—C8 | 1.209 (3) | N1—H1n | 0.85 (1) |
O4—C4 | 1.352 (3) | N2—H2n | 0.85 (1) |
O4—C7 | 1.406 (4) | C2'—H2' | 0.93 |
N1—C9 | 1.386 (3) | C3'—H3' | 0.93 |
N1—C8 | 1.391 (3) | C5'—H5' | 0.93 |
N2—C9 | 1.319 (3) | C6'—H6' | 0.93 |
N2—C10 | 1.459 (3) | C2—H2 | 0.93 |
C1—C2' | 1.382 (8) | C3—H3 | 0.93 |
C1—C2 | 1.383 (7) | C5—H5 | 0.93 |
C1—C6' | 1.393 (8) | C6—H6 | 0.93 |
C1—C6 | 1.397 (7) | C7—H7a | 0.96 |
C1—C8 | 1.480 (3) | C7—H7b | 0.96 |
C4—C3 | 1.375 (7) | C7—H7c | 0.96 |
C4—C3' | 1.380 (8) | C10—H10 | 0.98 |
C4—C5 | 1.388 (7) | C11—H11 | 0.98 |
C4—C5' | 1.398 (8) | C12—H12a | 0.96 |
C2'—C3' | 1.385 (8) | C12—H12b | 0.96 |
C5'—C6' | 1.375 (8) | C12—H12c | 0.96 |
C2—C3 | 1.384 (7) | C13—H13a | 0.96 |
C5—C6 | 1.364 (7) | C13—H13b | 0.96 |
C10—C14 | 1.508 (3) | C13—H13c | 0.96 |
C10—C11 | 1.537 (3) | ||
C4—O4—C7 | 118.8 (2) | C10—N2—H2n | 115 (2) |
C9—N1—C8 | 128.3 (2) | C1—C2'—H2' | 118.2 |
C9—N2—C10 | 122.3 (2) | C3'—C2'—H2' | 118.2 |
C2'—C1—C6' | 116.7 (9) | C4—C3'—H3' | 121.4 |
C2—C1—C6 | 119.3 (7) | C2'—C3'—H3' | 121.4 |
C2'—C1—C8 | 124.4 (5) | C6'—C5'—H5' | 121.0 |
C2—C1—C8 | 123.5 (4) | C4—C5'—H5' | 121.0 |
C6'—C1—C8 | 118.8 (5) | C5'—C6'—H6' | 118.8 |
C6—C1—C8 | 117.2 (4) | C1—C6'—H6' | 118.8 |
O4—C4—C3 | 124.3 (4) | C3—C2—H2 | 119.7 |
O4—C4—C3' | 122.4 (5) | C1—C2—H2 | 119.7 |
O4—C4—C5 | 117.0 (4) | C4—C3—H3 | 119.9 |
C3—C4—C5 | 118.7 (7) | C2—C3—H3 | 119.9 |
O4—C4—C5' | 115.6 (5) | C6—C5—H5 | 119.0 |
C3'—C4—C5' | 122.0 (9) | C4—C5—H5 | 119.0 |
C1—C2'—C3' | 124 (1) | C5—C6—H6 | 120.4 |
C4—C3'—C2' | 117.2 (9) | C1—C6—H6 | 120.4 |
C6'—C5'—C4 | 118 (1) | O4—C7—H7a | 109.5 |
C5'—C6'—C1 | 122 (1) | O4—C7—H7b | 109.5 |
C3—C2—C1 | 120.6 (7) | H7a—C7—H7b | 109.5 |
C4—C3—C2 | 120.2 (7) | O4—C7—H7c | 109.5 |
C6—C5—C4 | 122.0 (7) | H7a—C7—H7c | 109.5 |
C5—C6—C1 | 119.1 (7) | H7b—C7—H7c | 109.5 |
O3—C8—N1 | 121.2 (2) | N2—C10—H10 | 108.8 |
O3—C8—C1 | 123.5 (2) | C14—C10—H10 | 108.8 |
N1—C8—C1 | 115.3 (2) | C11—C10—H10 | 108.8 |
N2—C9—N1 | 117.3 (2) | C12—C11—H11 | 106.3 |
N2—C9—S1 | 123.4 (2) | C13—C11—H11 | 106.3 |
N1—C9—S1 | 119.2 (2) | C10—C11—H11 | 106.3 |
N2—C10—C14 | 108.3 (2) | C11—C12—H12a | 109.5 |
N2—C10—C11 | 109.9 (2) | C11—C12—H12b | 109.5 |
C14—C10—C11 | 112.2 (2) | H12a—C12—H12b | 109.5 |
C12—C11—C13 | 111.9 (2) | C11—C12—H12c | 109.5 |
C12—C11—C10 | 112.5 (2) | H12a—C12—H12c | 109.5 |
C13—C11—C10 | 112.9 (2) | H12b—C12—H12c | 109.5 |
O2—C14—O1 | 124.1 (2) | C11—C13—H13a | 109.5 |
O2—C14—C10 | 125.0 (2) | C11—C13—H13b | 109.5 |
O1—C14—C10 | 110.9 (2) | H13a—C13—H13b | 109.5 |
C14—O1—H1o | 110 (2) | C11—C13—H13c | 109.5 |
C9—N1—H1n | 113 (2) | H13a—C13—H13c | 109.5 |
C8—N1—H1n | 119 (2) | H13b—C13—H13c | 109.5 |
C9—N2—H2n | 122 (2) | ||
C7—O4—C4—C3 | −14.2 (8) | C9—N1—C8—O3 | −0.7 (4) |
C7—O4—C4—C3' | 11.6 (7) | C9—N1—C8—C1 | 177.9 (2) |
C7—O4—C4—C5 | 164.8 (7) | C2'—C1—C8—O3 | 162.5 (6) |
C7—O4—C4—C5' | −170.1 (6) | C2—C1—C8—O3 | −171.7 (7) |
C2—C1—C2'—C3' | 87 (2) | C6'—C1—C8—O3 | −15.7 (6) |
C6'—C1—C2'—C3' | 0.0 (3) | C6—C1—C8—O3 | 8.9 (7) |
C8—C1—C2'—C3' | −178.2 (3) | C2'—C1—C8—N1 | −16.2 (6) |
O4—C4—C3'—C2' | 177.6 (3) | C2—C1—C8—N1 | 9.7 (7) |
C5'—C4—C3'—C2' | −0.6 (6) | C6'—C1—C8—N1 | 165.6 (6) |
C1—C2'—C3'—C4 | 0.2 (3) | C6—C1—C8—N1 | −169.7 (7) |
O4—C4—C5'—C6' | −177.5 (5) | C10—N2—C9—N1 | −171.5 (2) |
C3'—C4—C5'—C6' | 0.7 (8) | C10—N2—C9—S1 | 8.8 (3) |
C4—C5'—C6'—C1 | −0.5 (8) | C8—N1—C9—N2 | −2.6 (4) |
C2'—C1—C6'—C5' | 0.2 (6) | C8—N1—C9—S1 | 177.0 (2) |
C8—C1—C6'—C5' | 178.5 (5) | C9—N2—C10—C14 | −155.1 (2) |
C6—C1—C2—C3 | 0.0 (3) | C9—N2—C10—C11 | 82.0 (3) |
C8—C1—C2—C3 | −179.4 (2) | N2—C10—C11—C12 | 68.4 (3) |
O4—C4—C3—C2 | 179.9 (3) | C14—C10—C11—C12 | −52.1 (3) |
C5—C4—C3—C2 | 0.9 (5) | N2—C10—C11—C13 | −163.7 (2) |
C1—C2—C3—C4 | −0.4 (3) | C14—C10—C11—C13 | 75.7 (3) |
O4—C4—C5—C6 | 179.8 (5) | N2—C10—C14—O2 | −18.2 (4) |
C3—C4—C5—C6 | −1.2 (7) | C11—C10—C14—O2 | 103.3 (3) |
C4—C5—C6—C1 | 0.8 (8) | N2—C10—C14—O1 | 163.1 (2) |
C2—C1—C6—C5 | −0.3 (6) | C11—C10—C14—O1 | −75.4 (3) |
C8—C1—C6—C5 | 179.2 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1o···S1i | 0.85 (1) | 2.25 (1) | 3.080 (2) | 165 (3) |
N2—H2n···O3 | 0.85 (1) | 2.03 (2) | 2.651 (3) | 129 (2) |
Symmetry code: (i) x, y−1, z. |