organic compounds
In the title molecule, C12H14N2O4S, the methoxybenzoyl group is trans to the thiono S atom across the C—N bond. The propionic acid group adopts a gauche conformation about the C—C bond, with a CCOOH—C—C—N torsion angle of 64.9 (4)°. In the crystal structure, intermolecular O—HS, N—HO and C—HO hydrogen bonds link the molecules into chains parallel to the c axis.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806026833/cv2082sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806026833/cv2082Isup2.hkl |
CCDC reference: 618183
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.006 Å
- R factor = 0.043
- wR factor = 0.106
- Data-to-parameter ratio = 10.4
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 25.00 From the CIF: _reflns_number_total 1792 Count of symmetry unique reflns 1175 Completeness (_total/calc) 152.51% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 617 Fraction of Friedel pairs measured 0.525 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 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 1 ALERT type 4 Improvement, methodology, query or suggestion
Computing details top
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).
3-[3-(4-methoxybenzoyl)thioureido]propionic acid top
Crystal data top
C12H14N2O4S | F(000) = 296 |
Mr = 282.31 | Dx = 1.411 Mg m−3 |
Monoclinic, Pc | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P -2yc | Cell parameters from 636 reflections |
a = 9.795 (3) Å | θ = 2.2–25.0° |
b = 4.7790 (13) Å | µ = 0.26 mm−1 |
c = 14.951 (4) Å | T = 298 K |
β = 108.275 (5)° | Plate, yellow |
V = 664.6 (3) Å3 | 0.34 × 0.17 × 0.07 mm |
Z = 2 |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 1792 independent reflections |
Radiation source: fine-focus sealed tube | 1660 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.019 |
Detector resolution: 83.66 pixels mm-1 | θmax = 25.0°, θmin = 2.2° |
ω scans | h = −9→11 |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | k = −5→5 |
Tmin = 0.912, Tmax = 0.979 | l = −17→17 |
3159 measured reflections |
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)] = 0.043 | H-atom parameters constrained |
wR(F2) = 0.106 | w = 1/[σ2(Fo2) + (0.0526P)2 + 0.0617P] where P = (Fo2 + 2Fc2)/3 |
S = 1.15 | (Δ/σ)max < 0.001 |
1792 reflections | Δρmax = 0.28 e Å−3 |
172 parameters | Δρmin = −0.15 e Å−3 |
2 restraints | Absolute structure: Flack (1983) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.16 (11) |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
S1 | 0.38629 (10) | −0.38705 (19) | 0.23542 (7) | 0.0556 (3) | |
O1 | 1.0598 (3) | 0.8691 (6) | 0.50390 (19) | 0.0666 (8) | |
O2 | 0.7374 (3) | 0.0951 (6) | 0.16476 (18) | 0.0578 (7) | |
O3 | 0.2748 (3) | −0.0679 (6) | −0.15426 (19) | 0.0621 (8) | |
H3 | 0.3022 | 0.0678 | −0.1776 | 0.093* | |
O4 | 0.5042 (3) | −0.0904 (6) | −0.06790 (17) | 0.0538 (7) | |
N1 | 0.6026 (3) | −0.0297 (6) | 0.25707 (19) | 0.0425 (7) | |
H1A | 0.5864 | 0.0065 | 0.3092 | 0.051* | |
N2 | 0.5386 (3) | −0.2939 (6) | 0.12120 (19) | 0.0485 (7) | |
H2A | 0.6072 | −0.2080 | 0.1082 | 0.058* | |
C1 | 0.7862 (5) | 0.3355 (9) | 0.4027 (3) | 0.0588 (11) | |
H1B | 0.7216 | 0.2210 | 0.4197 | 0.071* | |
C2 | 0.8709 (5) | 0.5207 (11) | 0.4685 (3) | 0.0634 (12) | |
H2B | 0.8616 | 0.5314 | 0.5284 | 0.076* | |
C3 | 0.9684 (4) | 0.6880 (8) | 0.4451 (3) | 0.0505 (9) | |
C4 | 0.9782 (4) | 0.6750 (8) | 0.3544 (3) | 0.0511 (9) | |
H4A | 1.0423 | 0.7910 | 0.3375 | 0.061* | |
C5 | 0.8940 (4) | 0.4926 (8) | 0.2899 (3) | 0.0478 (9) | |
H5A | 0.9025 | 0.4852 | 0.2297 | 0.057* | |
C6 | 0.7953 (4) | 0.3170 (7) | 0.3125 (2) | 0.0427 (8) | |
C7 | 1.0561 (6) | 0.8900 (11) | 0.5985 (3) | 0.0825 (16) | |
H7A | 1.1255 | 1.0257 | 0.6322 | 0.124* | |
H7B | 1.0785 | 0.7113 | 0.6289 | 0.124* | |
H7C | 0.9619 | 0.9471 | 0.5979 | 0.124* | |
C8 | 0.7119 (4) | 0.1219 (7) | 0.2399 (2) | 0.0416 (8) | |
C9 | 0.5164 (4) | −0.2310 (7) | 0.2014 (2) | 0.0421 (8) | |
C10 | 0.4560 (5) | −0.4982 (8) | 0.0525 (3) | 0.0547 (10) | |
H10A | 0.4186 | −0.6405 | 0.0849 | 0.066* | |
H10B | 0.5189 | −0.5892 | 0.0227 | 0.066* | |
C11 | 0.3323 (4) | −0.3616 (8) | −0.0223 (3) | 0.0518 (9) | |
H11A | 0.2744 | −0.5058 | −0.0622 | 0.062* | |
H11B | 0.2720 | −0.2635 | 0.0080 | 0.062* | |
C12 | 0.3816 (4) | −0.1610 (8) | −0.0818 (2) | 0.0449 (8) |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0630 (6) | 0.0511 (5) | 0.0539 (5) | −0.0134 (5) | 0.0201 (4) | −0.0049 (5) |
O1 | 0.0608 (19) | 0.0754 (19) | 0.0603 (18) | −0.0264 (15) | 0.0143 (15) | −0.0117 (14) |
O2 | 0.0648 (18) | 0.0664 (18) | 0.0479 (15) | −0.0121 (14) | 0.0259 (14) | −0.0057 (13) |
O3 | 0.0499 (16) | 0.080 (2) | 0.0535 (15) | 0.0136 (14) | 0.0126 (14) | 0.0121 (14) |
O4 | 0.0448 (17) | 0.0726 (19) | 0.0435 (14) | −0.0013 (13) | 0.0129 (12) | −0.0001 (12) |
N1 | 0.0471 (18) | 0.0452 (16) | 0.0374 (15) | −0.0030 (14) | 0.0163 (14) | −0.0023 (12) |
N2 | 0.0588 (19) | 0.0444 (17) | 0.0419 (16) | −0.0022 (15) | 0.0155 (14) | −0.0033 (13) |
C1 | 0.058 (2) | 0.074 (3) | 0.048 (2) | −0.027 (2) | 0.0215 (19) | −0.0061 (19) |
C2 | 0.065 (3) | 0.080 (3) | 0.050 (2) | −0.027 (2) | 0.024 (2) | −0.014 (2) |
C3 | 0.040 (2) | 0.056 (2) | 0.051 (2) | −0.0034 (17) | 0.0087 (17) | −0.0060 (17) |
C4 | 0.048 (2) | 0.052 (2) | 0.056 (2) | −0.0097 (18) | 0.0188 (18) | 0.0008 (17) |
C5 | 0.043 (2) | 0.057 (2) | 0.0442 (19) | 0.0013 (17) | 0.0156 (17) | 0.0019 (17) |
C6 | 0.0405 (19) | 0.0427 (19) | 0.0467 (19) | 0.0014 (15) | 0.0162 (16) | 0.0009 (15) |
C7 | 0.086 (4) | 0.099 (4) | 0.058 (3) | −0.039 (3) | 0.015 (2) | −0.021 (3) |
C8 | 0.038 (2) | 0.0447 (19) | 0.0403 (19) | 0.0029 (15) | 0.0101 (16) | 0.0046 (15) |
C9 | 0.046 (2) | 0.0338 (17) | 0.0397 (19) | 0.0084 (16) | 0.0043 (16) | 0.0040 (15) |
C10 | 0.071 (3) | 0.042 (2) | 0.050 (2) | −0.0024 (19) | 0.017 (2) | −0.0061 (17) |
C11 | 0.052 (2) | 0.060 (2) | 0.0434 (19) | −0.0089 (18) | 0.0149 (17) | −0.0079 (17) |
C12 | 0.048 (2) | 0.050 (2) | 0.0393 (18) | 0.0042 (17) | 0.0167 (17) | −0.0113 (15) |
Geometric parameters (Å, º) top
S1—C9 | 1.687 (4) | C2—H2B | 0.9300 |
O1—C3 | 1.353 (4) | C3—C4 | 1.391 (5) |
O1—C7 | 1.429 (5) | C4—C5 | 1.368 (5) |
O2—C8 | 1.231 (4) | C4—H4A | 0.9300 |
O3—C12 | 1.325 (4) | C5—C6 | 1.399 (5) |
O3—H3 | 0.8200 | C5—H5A | 0.9300 |
O4—C12 | 1.201 (5) | C6—C8 | 1.470 (5) |
N1—C9 | 1.375 (4) | C7—H7A | 0.9600 |
N1—C8 | 1.382 (5) | C7—H7B | 0.9600 |
N1—H1A | 0.8600 | C7—H7C | 0.9600 |
N2—C9 | 1.318 (4) | C10—C11 | 1.515 (6) |
N2—C10 | 1.463 (5) | C10—H10A | 0.9700 |
N2—H2A | 0.8600 | C10—H10B | 0.9700 |
C1—C6 | 1.381 (5) | C11—C12 | 1.488 (5) |
C1—C2 | 1.389 (6) | C11—H11A | 0.9700 |
C1—H1B | 0.9300 | C11—H11B | 0.9700 |
C2—C3 | 1.372 (6) | ||
C3—O1—C7 | 118.1 (3) | O1—C7—H7B | 109.5 |
C12—O3—H3 | 109.5 | H7A—C7—H7B | 109.5 |
C9—N1—C8 | 128.2 (3) | O1—C7—H7C | 109.5 |
C9—N1—H1A | 115.9 | H7A—C7—H7C | 109.5 |
C8—N1—H1A | 115.9 | H7B—C7—H7C | 109.5 |
C9—N2—C10 | 125.3 (3) | O2—C8—N1 | 120.4 (3) |
C9—N2—H2A | 117.4 | O2—C8—C6 | 121.0 (3) |
C10—N2—H2A | 117.4 | N1—C8—C6 | 118.6 (3) |
C6—C1—C2 | 121.7 (4) | N2—C9—N1 | 117.7 (3) |
C6—C1—H1B | 119.2 | N2—C9—S1 | 122.0 (3) |
C2—C1—H1B | 119.2 | N1—C9—S1 | 120.3 (3) |
C3—C2—C1 | 120.0 (4) | N2—C10—C11 | 111.7 (3) |
C3—C2—H2B | 120.0 | N2—C10—H10A | 109.3 |
C1—C2—H2B | 120.0 | C11—C10—H10A | 109.3 |
O1—C3—C2 | 125.4 (3) | N2—C10—H10B | 109.3 |
O1—C3—C4 | 115.4 (3) | C11—C10—H10B | 109.3 |
C2—C3—C4 | 119.3 (3) | H10A—C10—H10B | 108.0 |
C5—C4—C3 | 120.4 (3) | C12—C11—C10 | 112.6 (3) |
C5—C4—H4A | 119.8 | C12—C11—H11A | 109.1 |
C3—C4—H4A | 119.8 | C10—C11—H11A | 109.1 |
C4—C5—C6 | 121.4 (3) | C12—C11—H11B | 109.1 |
C4—C5—H5A | 119.3 | C10—C11—H11B | 109.1 |
C6—C5—H5A | 119.3 | H11A—C11—H11B | 107.8 |
C1—C6—C5 | 117.3 (3) | O4—C12—O3 | 122.5 (4) |
C1—C6—C8 | 124.8 (3) | O4—C12—C11 | 124.9 (4) |
C5—C6—C8 | 117.9 (3) | O3—C12—C11 | 112.6 (3) |
O1—C7—H7A | 109.5 | ||
C6—C1—C2—C3 | −1.1 (7) | C9—N1—C8—C6 | −176.7 (3) |
C7—O1—C3—C2 | 0.2 (7) | C1—C6—C8—O2 | −171.7 (4) |
C7—O1—C3—C4 | −179.4 (4) | C5—C6—C8—O2 | 6.7 (5) |
C1—C2—C3—O1 | −177.7 (4) | C1—C6—C8—N1 | 9.0 (5) |
C1—C2—C3—C4 | 1.8 (7) | C5—C6—C8—N1 | −172.6 (3) |
O1—C3—C4—C5 | 178.0 (4) | C10—N2—C9—N1 | −178.8 (3) |
C2—C3—C4—C5 | −1.6 (6) | C10—N2—C9—S1 | 0.6 (5) |
C3—C4—C5—C6 | 0.6 (6) | C8—N1—C9—N2 | 0.5 (5) |
C2—C1—C6—C5 | 0.1 (6) | C8—N1—C9—S1 | −178.9 (3) |
C2—C1—C6—C8 | 178.5 (4) | N2—C10—C11—C12 | 64.9 (4) |
C4—C5—C6—C1 | 0.1 (6) | C10—C11—C12—O4 | −7.0 (5) |
C4—C5—C6—C8 | −178.4 (3) | C10—C11—C12—O3 | 172.2 (3) |
C9—N1—C8—O2 | 4.0 (5) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O2 | 0.86 | 1.94 | 2.622 (4) | 135 |
N2—H2A···O4 | 0.86 | 2.57 | 2.908 (4) | 105 |
C10—H10A···S1 | 0.97 | 2.66 | 3.066 (5) | 105 |
O3—H3···S1i | 0.82 | 2.32 | 3.126 (3) | 169 |
N1—H1A···O4ii | 0.86 | 2.26 | 3.113 (4) | 170 |
C1—H1B···O4ii | 0.93 | 2.28 | 3.155 (6) | 156 |
Symmetry codes: (i) x, −y, z−1/2; (ii) x, −y, z+1/2. |