organic compounds
In the title compound, C20H19N3O4S, the 3-methylene-1H-indole unit is nearly planar with a dihedral angle of 2.69 (2)° between the rings. The crystal structure is stabilized by intermolecular N—HO, N—HS, O—HS and C—HO hydrogen bonds, forming a two-dimensional network approximately parallel to the (011) plane.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806004065/hk6084sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806004065/hk6084Isup2.hkl |
CCDC reference: 601196
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.004 Å
- R factor = 0.071
- wR factor = 0.139
- Data-to-parameter ratio = 13.1
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5 PLAT432_ALERT_2_C Short Inter X...Y Contact O3 .. C2 .. 2.99 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 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 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion
checkCIF publication errors
Alert level A PUBL023_ALERT_1_A There is a mismatched ^ on line 351 'calc w=1/[\s2^(Fo2^)+(0.0428P)2^+2.2534P] where P=(Fo2^+2Fc2^)/3' If you require a ^ then it should be escaped with a \, i.e. \^ Otherwise there must be a matching closing ~, e.g. ^12^C
1 ALERT level A = Data missing that is essential or data in wrong format 0 ALERT level G = General alerts. Data that may be required is missing
Computing details top
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).
3-(1H-Indol-3-yl)-2-[3-(4-methoxybenzoyl)thioureido]propionic acid top
Crystal data top
C20H19N3O4S | F(000) = 1664 |
Mr = 397.44 | Dx = 1.394 Mg m−3 |
Orthorhombic, Pbcn | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2n 2ab | Cell parameters from 781 reflections |
a = 18.247 (4) Å | θ = 1.8–25.0° |
b = 14.083 (3) Å | µ = 0.20 mm−1 |
c = 14.736 (3) Å | T = 298 K |
V = 3787.0 (14) Å3 | Block, colorless |
Z = 8 | 0.19 × 0.16 × 0.15 mm |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 3343 independent reflections |
Radiation source: fine-focus sealed tube | 2772 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.043 |
Detector resolution: 83.66 pixels mm-1 | θmax = 25.0°, θmin = 1.8° |
ω scans | h = −21→19 |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | k = −13→16 |
Tmin = 0.962, Tmax = 0.970 | l = −17→17 |
18371 measured reflections |
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)] = 0.071 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.139 | H-atom parameters constrained |
S = 1.26 | w = 1/[σ2(Fo2) + (0.0428P)2 + 2.2534P] where P = (Fo2 + 2Fc2)/3 |
3343 reflections | (Δ/σ)max < 0.001 |
255 parameters | Δρmax = 0.22 e Å−3 |
0 restraints | Δρmin = −0.22 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
S1 | 0.59694 (5) | 0.90541 (7) | 0.18486 (5) | 0.0556 (3) | |
O1 | 0.99771 (13) | 1.15890 (18) | −0.03042 (15) | 0.0616 (7) | |
O2 | 0.81750 (12) | 0.99523 (19) | 0.29934 (14) | 0.0596 (7) | |
O3 | 0.69494 (12) | 0.98072 (17) | 0.49981 (14) | 0.0532 (6) | |
O4 | 0.57986 (13) | 0.9375 (2) | 0.52763 (16) | 0.0655 (7) | |
H4 | 0.5841 | 0.9735 | 0.5711 | 0.098* | |
N1 | 0.73433 (12) | 0.96631 (18) | 0.18760 (16) | 0.0423 (6) | |
H1A | 0.7280 | 0.9682 | 0.1298 | 0.051* | |
N2 | 0.68560 (13) | 0.92567 (19) | 0.32609 (16) | 0.0431 (6) | |
H2A | 0.7273 | 0.9421 | 0.3483 | 0.052* | |
N3 | 0.8036 (2) | 0.7103 (2) | 0.5208 (2) | 0.0701 (9) | |
H3A | 0.8290 | 0.7011 | 0.5691 | 0.084* | |
C1 | 0.85237 (15) | 1.0350 (2) | 0.14956 (19) | 0.0400 (7) | |
C2 | 0.85121 (15) | 1.0085 (2) | 0.0590 (2) | 0.0431 (7) | |
H2 | 0.8174 | 0.9635 | 0.0395 | 0.052* | |
C3 | 0.89936 (16) | 1.0475 (2) | −0.0027 (2) | 0.0443 (8) | |
H3 | 0.8981 | 1.0285 | −0.0631 | 0.053* | |
C4 | 0.94919 (16) | 1.1144 (2) | 0.0250 (2) | 0.0455 (8) | |
C5 | 0.95175 (17) | 1.1412 (3) | 0.1158 (2) | 0.0533 (9) | |
H5 | 0.9856 | 1.1863 | 0.1350 | 0.064* | |
C6 | 0.90440 (16) | 1.1013 (2) | 0.1768 (2) | 0.0495 (8) | |
H6 | 0.9071 | 1.1187 | 0.2375 | 0.059* | |
C7 | 0.9960 (2) | 1.1356 (3) | −0.1247 (2) | 0.0678 (11) | |
H7A | 1.0062 | 1.0692 | −0.1323 | 0.102* | |
H7B | 1.0322 | 1.1723 | −0.1563 | 0.102* | |
H7C | 0.9483 | 1.1496 | −0.1488 | 0.102* | |
C8 | 0.80210 (15) | 0.9969 (2) | 0.2193 (2) | 0.0420 (7) | |
C9 | 0.67605 (16) | 0.9333 (2) | 0.23808 (19) | 0.0411 (7) | |
C10 | 0.62998 (17) | 0.8913 (2) | 0.3879 (2) | 0.0456 (8) | |
H10 | 0.5816 | 0.9063 | 0.3630 | 0.055* | |
C11 | 0.63555 (18) | 0.7834 (2) | 0.4018 (2) | 0.0546 (9) | |
H11A | 0.5995 | 0.7643 | 0.4466 | 0.066* | |
H11B | 0.6233 | 0.7521 | 0.3452 | 0.066* | |
C12 | 0.70946 (19) | 0.7497 (2) | 0.4322 (2) | 0.0505 (8) | |
C13 | 0.76977 (19) | 0.7214 (2) | 0.3761 (2) | 0.0498 (8) | |
C14 | 0.7801 (2) | 0.7114 (3) | 0.2825 (2) | 0.0621 (10) | |
H14 | 0.7433 | 0.7282 | 0.2420 | 0.074* | |
C15 | 0.8456 (2) | 0.6765 (3) | 0.2518 (3) | 0.0759 (12) | |
H15 | 0.8530 | 0.6698 | 0.1897 | 0.091* | |
C16 | 0.9012 (2) | 0.6509 (3) | 0.3115 (3) | 0.0819 (13) | |
H16 | 0.9447 | 0.6262 | 0.2885 | 0.098* | |
C17 | 0.8936 (2) | 0.6612 (3) | 0.4032 (3) | 0.0748 (11) | |
H17 | 0.9312 | 0.6453 | 0.4430 | 0.090* | |
C18 | 0.8274 (2) | 0.6963 (2) | 0.4344 (3) | 0.0570 (9) | |
C19 | 0.7333 (2) | 0.7412 (3) | 0.5185 (2) | 0.0624 (10) | |
H19 | 0.7052 | 0.7547 | 0.5695 | 0.075* | |
C20 | 0.63924 (17) | 0.9427 (2) | 0.4766 (2) | 0.0431 (7) |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0445 (5) | 0.0799 (7) | 0.0423 (4) | −0.0170 (5) | 0.0003 (4) | 0.0002 (4) |
O1 | 0.0536 (14) | 0.0729 (17) | 0.0584 (14) | −0.0101 (13) | 0.0106 (12) | 0.0123 (13) |
O2 | 0.0442 (12) | 0.0959 (19) | 0.0388 (13) | −0.0113 (13) | −0.0064 (10) | 0.0094 (12) |
O3 | 0.0417 (13) | 0.0713 (17) | 0.0467 (13) | −0.0040 (12) | 0.0000 (10) | −0.0094 (11) |
O4 | 0.0525 (14) | 0.089 (2) | 0.0550 (15) | −0.0134 (13) | 0.0199 (12) | −0.0149 (13) |
N1 | 0.0366 (14) | 0.0588 (17) | 0.0315 (12) | −0.0058 (12) | 0.0021 (11) | 0.0020 (12) |
N2 | 0.0349 (13) | 0.0575 (17) | 0.0369 (14) | −0.0060 (12) | 0.0010 (11) | 0.0012 (12) |
N3 | 0.094 (3) | 0.062 (2) | 0.0538 (19) | 0.0031 (19) | −0.0131 (18) | 0.0062 (16) |
C1 | 0.0301 (15) | 0.0469 (19) | 0.0429 (16) | 0.0029 (14) | −0.0031 (13) | −0.0003 (14) |
C2 | 0.0320 (15) | 0.052 (2) | 0.0454 (17) | −0.0013 (15) | −0.0005 (14) | −0.0042 (15) |
C3 | 0.0370 (16) | 0.060 (2) | 0.0362 (15) | 0.0021 (16) | 0.0033 (14) | −0.0017 (15) |
C4 | 0.0364 (17) | 0.0503 (19) | 0.0499 (18) | 0.0027 (15) | 0.0039 (14) | 0.0052 (16) |
C5 | 0.0404 (18) | 0.062 (2) | 0.057 (2) | −0.0125 (16) | 0.0001 (16) | −0.0070 (18) |
C6 | 0.0433 (18) | 0.063 (2) | 0.0426 (17) | −0.0023 (17) | −0.0008 (15) | −0.0075 (16) |
C7 | 0.070 (2) | 0.075 (3) | 0.059 (2) | 0.005 (2) | 0.0226 (19) | 0.015 (2) |
C8 | 0.0349 (16) | 0.0496 (19) | 0.0416 (18) | 0.0017 (15) | −0.0002 (13) | 0.0019 (14) |
C9 | 0.0431 (17) | 0.0440 (18) | 0.0362 (16) | 0.0007 (14) | 0.0069 (13) | −0.0007 (14) |
C10 | 0.0371 (16) | 0.061 (2) | 0.0391 (16) | −0.0088 (15) | 0.0041 (14) | 0.0023 (16) |
C11 | 0.058 (2) | 0.063 (2) | 0.0431 (18) | −0.0233 (18) | 0.0107 (16) | −0.0066 (17) |
C12 | 0.066 (2) | 0.0393 (19) | 0.0461 (18) | −0.0130 (17) | 0.0063 (16) | 0.0028 (15) |
C13 | 0.063 (2) | 0.0363 (18) | 0.0505 (18) | −0.0128 (16) | 0.0020 (17) | 0.0002 (15) |
C14 | 0.072 (2) | 0.064 (2) | 0.051 (2) | −0.010 (2) | 0.0091 (18) | −0.0002 (18) |
C15 | 0.084 (3) | 0.074 (3) | 0.070 (3) | −0.003 (2) | 0.025 (2) | 0.001 (2) |
C16 | 0.069 (3) | 0.068 (3) | 0.109 (4) | 0.000 (2) | 0.032 (3) | 0.003 (3) |
C17 | 0.068 (3) | 0.061 (3) | 0.096 (3) | −0.007 (2) | −0.001 (2) | 0.010 (2) |
C18 | 0.070 (2) | 0.039 (2) | 0.062 (2) | −0.0101 (18) | −0.0047 (19) | 0.0067 (17) |
C19 | 0.087 (3) | 0.058 (2) | 0.0420 (19) | 0.002 (2) | 0.0076 (19) | 0.0045 (17) |
C20 | 0.0397 (18) | 0.050 (2) | 0.0390 (16) | 0.0036 (15) | 0.0035 (14) | 0.0045 (15) |
Geometric parameters (Å, º) top
S1—C9 | 1.689 (3) | C5—H5 | 0.9300 |
O1—C4 | 1.358 (4) | C6—H6 | 0.9300 |
O1—C7 | 1.428 (4) | C7—H7A | 0.9600 |
O2—C8 | 1.213 (3) | C7—H7B | 0.9600 |
O3—C20 | 1.199 (4) | C7—H7C | 0.9600 |
O4—C20 | 1.321 (4) | C10—C20 | 1.503 (4) |
O4—H4 | 0.8200 | C10—C11 | 1.536 (5) |
N1—C9 | 1.379 (4) | C10—H10 | 0.9800 |
N1—C8 | 1.390 (4) | C11—C12 | 1.498 (5) |
N1—H1A | 0.8600 | C11—H11A | 0.9700 |
N2—C9 | 1.313 (4) | C11—H11B | 0.9700 |
N2—C10 | 1.448 (4) | C12—C19 | 1.349 (5) |
N2—H2A | 0.8600 | C12—C13 | 1.432 (5) |
N3—C19 | 1.355 (5) | C13—C14 | 1.399 (5) |
N3—C18 | 1.360 (5) | C13—C18 | 1.402 (5) |
N3—H3A | 0.8600 | C14—C15 | 1.369 (5) |
C1—C2 | 1.386 (4) | C14—H14 | 0.9300 |
C1—C6 | 1.391 (4) | C15—C16 | 1.391 (6) |
C1—C8 | 1.478 (4) | C15—H15 | 0.9300 |
C2—C3 | 1.379 (4) | C16—C17 | 1.367 (6) |
C2—H2 | 0.9300 | C16—H16 | 0.9300 |
C3—C4 | 1.372 (4) | C17—C18 | 1.383 (5) |
C3—H3 | 0.9300 | C17—H17 | 0.9300 |
C4—C5 | 1.390 (4) | C19—H19 | 0.9300 |
C5—C6 | 1.368 (4) | ||
C4—O1—C7 | 117.7 (3) | N1—C9—S1 | 119.1 (2) |
C20—O4—H4 | 109.5 | N2—C10—C20 | 107.9 (2) |
C9—N1—C8 | 127.6 (2) | N2—C10—C11 | 111.6 (3) |
C9—N1—H1A | 116.2 | C20—C10—C11 | 110.7 (3) |
C8—N1—H1A | 116.2 | N2—C10—H10 | 108.9 |
C9—N2—C10 | 123.8 (3) | C20—C10—H10 | 108.9 |
C9—N2—H2A | 118.1 | C11—C10—H10 | 108.9 |
C10—N2—H2A | 118.1 | C12—C11—C10 | 114.4 (3) |
C19—N3—C18 | 109.0 (3) | C12—C11—H11A | 108.7 |
C19—N3—H3A | 125.5 | C10—C11—H11A | 108.7 |
C18—N3—H3A | 125.5 | C12—C11—H11B | 108.7 |
C2—C1—C6 | 118.0 (3) | C10—C11—H11B | 108.7 |
C2—C1—C8 | 124.2 (3) | H11A—C11—H11B | 107.6 |
C6—C1—C8 | 117.8 (3) | C19—C12—C13 | 105.7 (3) |
C3—C2—C1 | 121.2 (3) | C19—C12—C11 | 126.8 (3) |
C3—C2—H2 | 119.4 | C13—C12—C11 | 127.4 (3) |
C1—C2—H2 | 119.4 | C14—C13—C18 | 118.5 (3) |
C4—C3—C2 | 120.0 (3) | C14—C13—C12 | 134.4 (3) |
C4—C3—H3 | 120.0 | C18—C13—C12 | 107.0 (3) |
C2—C3—H3 | 120.0 | C15—C14—C13 | 118.7 (4) |
O1—C4—C3 | 124.7 (3) | C15—C14—H14 | 120.7 |
O1—C4—C5 | 115.6 (3) | C13—C14—H14 | 120.7 |
C3—C4—C5 | 119.7 (3) | C14—C15—C16 | 121.4 (4) |
C6—C5—C4 | 119.9 (3) | C14—C15—H15 | 119.3 |
C6—C5—H5 | 120.0 | C16—C15—H15 | 119.3 |
C4—C5—H5 | 120.0 | C17—C16—C15 | 121.5 (4) |
C5—C6—C1 | 121.2 (3) | C17—C16—H16 | 119.2 |
C5—C6—H6 | 119.4 | C15—C16—H16 | 119.2 |
C1—C6—H6 | 119.4 | C16—C17—C18 | 117.1 (4) |
O1—C7—H7A | 109.5 | C16—C17—H17 | 121.4 |
O1—C7—H7B | 109.5 | C18—C17—H17 | 121.4 |
H7A—C7—H7B | 109.5 | N3—C18—C17 | 129.9 (4) |
O1—C7—H7C | 109.5 | N3—C18—C13 | 107.3 (3) |
H7A—C7—H7C | 109.5 | C17—C18—C13 | 122.8 (4) |
H7B—C7—H7C | 109.5 | C12—C19—N3 | 110.9 (3) |
O2—C8—N1 | 121.8 (3) | C12—C19—H19 | 124.5 |
O2—C8—C1 | 122.6 (3) | N3—C19—H19 | 124.5 |
N1—C8—C1 | 115.5 (3) | O3—C20—O4 | 123.9 (3) |
N2—C9—N1 | 117.3 (3) | O3—C20—C10 | 124.0 (3) |
N2—C9—S1 | 123.6 (2) | O4—C20—C10 | 112.1 (3) |
C6—C1—C2—C3 | −1.0 (5) | C10—C11—C12—C19 | 89.0 (4) |
C8—C1—C2—C3 | 179.4 (3) | C10—C11—C12—C13 | −89.8 (4) |
C1—C2—C3—C4 | −0.5 (5) | C19—C12—C13—C14 | 177.7 (4) |
C7—O1—C4—C3 | 1.1 (5) | C11—C12—C13—C14 | −3.3 (6) |
C7—O1—C4—C5 | −178.4 (3) | C19—C12—C13—C18 | 0.4 (4) |
C2—C3—C4—O1 | −178.3 (3) | C11—C12—C13—C18 | 179.4 (3) |
C2—C3—C4—C5 | 1.2 (5) | C18—C13—C14—C15 | 0.9 (5) |
O1—C4—C5—C6 | 179.2 (3) | C12—C13—C14—C15 | −176.1 (4) |
C3—C4—C5—C6 | −0.3 (5) | C13—C14—C15—C16 | 0.1 (6) |
C4—C5—C6—C1 | −1.2 (5) | C14—C15—C16—C17 | −1.3 (7) |
C2—C1—C6—C5 | 1.8 (5) | C15—C16—C17—C18 | 1.4 (6) |
C8—C1—C6—C5 | −178.6 (3) | C19—N3—C18—C17 | −176.6 (4) |
C9—N1—C8—O2 | 1.7 (5) | C19—N3—C18—C13 | 1.2 (4) |
C9—N1—C8—C1 | −175.9 (3) | C16—C17—C18—N3 | 177.1 (4) |
C2—C1—C8—O2 | 155.1 (3) | C16—C17—C18—C13 | −0.3 (6) |
C6—C1—C8—O2 | −24.5 (5) | C14—C13—C18—N3 | −178.8 (3) |
C2—C1—C8—N1 | −27.4 (4) | C12—C13—C18—N3 | −1.0 (4) |
C6—C1—C8—N1 | 153.0 (3) | C14—C13—C18—C17 | −0.8 (5) |
C10—N2—C9—N1 | −179.4 (3) | C12—C13—C18—C17 | 177.0 (3) |
C10—N2—C9—S1 | 0.9 (4) | C13—C12—C19—N3 | 0.3 (4) |
C8—N1—C9—N2 | −3.0 (5) | C11—C12—C19—N3 | −178.8 (3) |
C8—N1—C9—S1 | 176.7 (2) | C18—N3—C19—C12 | −0.9 (4) |
C9—N2—C10—C20 | −147.0 (3) | N2—C10—C20—O3 | −21.3 (4) |
C9—N2—C10—C11 | 91.2 (4) | C11—C10—C20—O3 | 101.1 (4) |
N2—C10—C11—C12 | 54.7 (4) | N2—C10—C20—O4 | 161.6 (3) |
C20—C10—C11—C12 | −65.5 (3) | C11—C10—C20—O4 | −76.0 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C10—H10···S1 | 0.98 | 2.64 | 3.059 (3) | 106 |
N2—H2A···O2 | 0.86 | 1.95 | 2.628 (3) | 135 |
N2—H2A···O3 | 0.86 | 2.37 | 2.680 (3) | 102 |
N1—H1A···O3i | 0.86 | 2.13 | 2.955 (3) | 160 |
N3—H3A···S1ii | 0.86 | 2.64 | 3.434 (3) | 154 |
O4—H4···S1iii | 0.82 | 2.40 | 3.219 (3) | 173 |
C2—H2···O3i | 0.93 | 2.44 | 2.986 (4) | 118 |
C3—H3···O2i | 0.93 | 2.53 | 3.332 (4) | 145 |
Symmetry codes: (i) x, −y+2, z−1/2; (ii) −x+3/2, −y+3/2, z+1/2; (iii) x, −y+2, z+1/2. |