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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—H...O, N—H...S, O—H...S and C—H...O hydrogen bonds, forming a two-dimensional network approximately parallel to the (011) plane.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806004065/hk6084sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806004065/hk6084Isup2.hkl
Contains datablock I

CCDC reference: 601196

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](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
C20H19N3O4SF(000) = 1664
Mr = 397.44Dx = 1.394 Mg m3
Orthorhombic, PbcnMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2abCell parameters from 781 reflections
a = 18.247 (4) Åθ = 1.8–25.0°
b = 14.083 (3) ŵ = 0.20 mm1
c = 14.736 (3) ÅT = 298 K
V = 3787.0 (14) Å3Block, colorless
Z = 80.19 × 0.16 × 0.15 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
3343 independent reflections
Radiation source: fine-focus sealed tube2772 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.043
Detector resolution: 83.66 pixels mm-1θmax = 25.0°, θmin = 1.8°
ω scansh = 2119
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
k = 1316
Tmin = 0.962, Tmax = 0.970l = 1717
18371 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.071Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.139H-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 parametersΔρmax = 0.22 e Å3
0 restraintsΔρmin = 0.22 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.59694 (5)0.90541 (7)0.18486 (5)0.0556 (3)
O10.99771 (13)1.15890 (18)0.03042 (15)0.0616 (7)
O20.81750 (12)0.99523 (19)0.29934 (14)0.0596 (7)
O30.69494 (12)0.98072 (17)0.49981 (14)0.0532 (6)
O40.57986 (13)0.9375 (2)0.52763 (16)0.0655 (7)
H40.58410.97350.57110.098*
N10.73433 (12)0.96631 (18)0.18760 (16)0.0423 (6)
H1A0.72800.96820.12980.051*
N20.68560 (13)0.92567 (19)0.32609 (16)0.0431 (6)
H2A0.72730.94210.34830.052*
N30.8036 (2)0.7103 (2)0.5208 (2)0.0701 (9)
H3A0.82900.70110.56910.084*
C10.85237 (15)1.0350 (2)0.14956 (19)0.0400 (7)
C20.85121 (15)1.0085 (2)0.0590 (2)0.0431 (7)
H20.81740.96350.03950.052*
C30.89936 (16)1.0475 (2)0.0027 (2)0.0443 (8)
H30.89811.02850.06310.053*
C40.94919 (16)1.1144 (2)0.0250 (2)0.0455 (8)
C50.95175 (17)1.1412 (3)0.1158 (2)0.0533 (9)
H50.98561.18630.13500.064*
C60.90440 (16)1.1013 (2)0.1768 (2)0.0495 (8)
H60.90711.11870.23750.059*
C70.9960 (2)1.1356 (3)0.1247 (2)0.0678 (11)
H7A1.00621.06920.13230.102*
H7B1.03221.17230.15630.102*
H7C0.94831.14960.14880.102*
C80.80210 (15)0.9969 (2)0.2193 (2)0.0420 (7)
C90.67605 (16)0.9333 (2)0.23808 (19)0.0411 (7)
C100.62998 (17)0.8913 (2)0.3879 (2)0.0456 (8)
H100.58160.90630.36300.055*
C110.63555 (18)0.7834 (2)0.4018 (2)0.0546 (9)
H11A0.59950.76430.44660.066*
H11B0.62330.75210.34520.066*
C120.70946 (19)0.7497 (2)0.4322 (2)0.0505 (8)
C130.76977 (19)0.7214 (2)0.3761 (2)0.0498 (8)
C140.7801 (2)0.7114 (3)0.2825 (2)0.0621 (10)
H140.74330.72820.24200.074*
C150.8456 (2)0.6765 (3)0.2518 (3)0.0759 (12)
H150.85300.66980.18970.091*
C160.9012 (2)0.6509 (3)0.3115 (3)0.0819 (13)
H160.94470.62620.28850.098*
C170.8936 (2)0.6612 (3)0.4032 (3)0.0748 (11)
H170.93120.64530.44300.090*
C180.8274 (2)0.6963 (2)0.4344 (3)0.0570 (9)
C190.7333 (2)0.7412 (3)0.5185 (2)0.0624 (10)
H190.70520.75470.56950.075*
C200.63924 (17)0.9427 (2)0.4766 (2)0.0431 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0445 (5)0.0799 (7)0.0423 (4)0.0170 (5)0.0003 (4)0.0002 (4)
O10.0536 (14)0.0729 (17)0.0584 (14)0.0101 (13)0.0106 (12)0.0123 (13)
O20.0442 (12)0.0959 (19)0.0388 (13)0.0113 (13)0.0064 (10)0.0094 (12)
O30.0417 (13)0.0713 (17)0.0467 (13)0.0040 (12)0.0000 (10)0.0094 (11)
O40.0525 (14)0.089 (2)0.0550 (15)0.0134 (13)0.0199 (12)0.0149 (13)
N10.0366 (14)0.0588 (17)0.0315 (12)0.0058 (12)0.0021 (11)0.0020 (12)
N20.0349 (13)0.0575 (17)0.0369 (14)0.0060 (12)0.0010 (11)0.0012 (12)
N30.094 (3)0.062 (2)0.0538 (19)0.0031 (19)0.0131 (18)0.0062 (16)
C10.0301 (15)0.0469 (19)0.0429 (16)0.0029 (14)0.0031 (13)0.0003 (14)
C20.0320 (15)0.052 (2)0.0454 (17)0.0013 (15)0.0005 (14)0.0042 (15)
C30.0370 (16)0.060 (2)0.0362 (15)0.0021 (16)0.0033 (14)0.0017 (15)
C40.0364 (17)0.0503 (19)0.0499 (18)0.0027 (15)0.0039 (14)0.0052 (16)
C50.0404 (18)0.062 (2)0.057 (2)0.0125 (16)0.0001 (16)0.0070 (18)
C60.0433 (18)0.063 (2)0.0426 (17)0.0023 (17)0.0008 (15)0.0075 (16)
C70.070 (2)0.075 (3)0.059 (2)0.005 (2)0.0226 (19)0.015 (2)
C80.0349 (16)0.0496 (19)0.0416 (18)0.0017 (15)0.0002 (13)0.0019 (14)
C90.0431 (17)0.0440 (18)0.0362 (16)0.0007 (14)0.0069 (13)0.0007 (14)
C100.0371 (16)0.061 (2)0.0391 (16)0.0088 (15)0.0041 (14)0.0023 (16)
C110.058 (2)0.063 (2)0.0431 (18)0.0233 (18)0.0107 (16)0.0066 (17)
C120.066 (2)0.0393 (19)0.0461 (18)0.0130 (17)0.0063 (16)0.0028 (15)
C130.063 (2)0.0363 (18)0.0505 (18)0.0128 (16)0.0020 (17)0.0002 (15)
C140.072 (2)0.064 (2)0.051 (2)0.010 (2)0.0091 (18)0.0002 (18)
C150.084 (3)0.074 (3)0.070 (3)0.003 (2)0.025 (2)0.001 (2)
C160.069 (3)0.068 (3)0.109 (4)0.000 (2)0.032 (3)0.003 (3)
C170.068 (3)0.061 (3)0.096 (3)0.007 (2)0.001 (2)0.010 (2)
C180.070 (2)0.039 (2)0.062 (2)0.0101 (18)0.0047 (19)0.0067 (17)
C190.087 (3)0.058 (2)0.0420 (19)0.002 (2)0.0076 (19)0.0045 (17)
C200.0397 (18)0.050 (2)0.0390 (16)0.0036 (15)0.0035 (14)0.0045 (15)
Geometric parameters (Å, º) top
S1—C91.689 (3)C5—H50.9300
O1—C41.358 (4)C6—H60.9300
O1—C71.428 (4)C7—H7A0.9600
O2—C81.213 (3)C7—H7B0.9600
O3—C201.199 (4)C7—H7C0.9600
O4—C201.321 (4)C10—C201.503 (4)
O4—H40.8200C10—C111.536 (5)
N1—C91.379 (4)C10—H100.9800
N1—C81.390 (4)C11—C121.498 (5)
N1—H1A0.8600C11—H11A0.9700
N2—C91.313 (4)C11—H11B0.9700
N2—C101.448 (4)C12—C191.349 (5)
N2—H2A0.8600C12—C131.432 (5)
N3—C191.355 (5)C13—C141.399 (5)
N3—C181.360 (5)C13—C181.402 (5)
N3—H3A0.8600C14—C151.369 (5)
C1—C21.386 (4)C14—H140.9300
C1—C61.391 (4)C15—C161.391 (6)
C1—C81.478 (4)C15—H150.9300
C2—C31.379 (4)C16—C171.367 (6)
C2—H20.9300C16—H160.9300
C3—C41.372 (4)C17—C181.383 (5)
C3—H30.9300C17—H170.9300
C4—C51.390 (4)C19—H190.9300
C5—C61.368 (4)
C4—O1—C7117.7 (3)N1—C9—S1119.1 (2)
C20—O4—H4109.5N2—C10—C20107.9 (2)
C9—N1—C8127.6 (2)N2—C10—C11111.6 (3)
C9—N1—H1A116.2C20—C10—C11110.7 (3)
C8—N1—H1A116.2N2—C10—H10108.9
C9—N2—C10123.8 (3)C20—C10—H10108.9
C9—N2—H2A118.1C11—C10—H10108.9
C10—N2—H2A118.1C12—C11—C10114.4 (3)
C19—N3—C18109.0 (3)C12—C11—H11A108.7
C19—N3—H3A125.5C10—C11—H11A108.7
C18—N3—H3A125.5C12—C11—H11B108.7
C2—C1—C6118.0 (3)C10—C11—H11B108.7
C2—C1—C8124.2 (3)H11A—C11—H11B107.6
C6—C1—C8117.8 (3)C19—C12—C13105.7 (3)
C3—C2—C1121.2 (3)C19—C12—C11126.8 (3)
C3—C2—H2119.4C13—C12—C11127.4 (3)
C1—C2—H2119.4C14—C13—C18118.5 (3)
C4—C3—C2120.0 (3)C14—C13—C12134.4 (3)
C4—C3—H3120.0C18—C13—C12107.0 (3)
C2—C3—H3120.0C15—C14—C13118.7 (4)
O1—C4—C3124.7 (3)C15—C14—H14120.7
O1—C4—C5115.6 (3)C13—C14—H14120.7
C3—C4—C5119.7 (3)C14—C15—C16121.4 (4)
C6—C5—C4119.9 (3)C14—C15—H15119.3
C6—C5—H5120.0C16—C15—H15119.3
C4—C5—H5120.0C17—C16—C15121.5 (4)
C5—C6—C1121.2 (3)C17—C16—H16119.2
C5—C6—H6119.4C15—C16—H16119.2
C1—C6—H6119.4C16—C17—C18117.1 (4)
O1—C7—H7A109.5C16—C17—H17121.4
O1—C7—H7B109.5C18—C17—H17121.4
H7A—C7—H7B109.5N3—C18—C17129.9 (4)
O1—C7—H7C109.5N3—C18—C13107.3 (3)
H7A—C7—H7C109.5C17—C18—C13122.8 (4)
H7B—C7—H7C109.5C12—C19—N3110.9 (3)
O2—C8—N1121.8 (3)C12—C19—H19124.5
O2—C8—C1122.6 (3)N3—C19—H19124.5
N1—C8—C1115.5 (3)O3—C20—O4123.9 (3)
N2—C9—N1117.3 (3)O3—C20—C10124.0 (3)
N2—C9—S1123.6 (2)O4—C20—C10112.1 (3)
C6—C1—C2—C31.0 (5)C10—C11—C12—C1989.0 (4)
C8—C1—C2—C3179.4 (3)C10—C11—C12—C1389.8 (4)
C1—C2—C3—C40.5 (5)C19—C12—C13—C14177.7 (4)
C7—O1—C4—C31.1 (5)C11—C12—C13—C143.3 (6)
C7—O1—C4—C5178.4 (3)C19—C12—C13—C180.4 (4)
C2—C3—C4—O1178.3 (3)C11—C12—C13—C18179.4 (3)
C2—C3—C4—C51.2 (5)C18—C13—C14—C150.9 (5)
O1—C4—C5—C6179.2 (3)C12—C13—C14—C15176.1 (4)
C3—C4—C5—C60.3 (5)C13—C14—C15—C160.1 (6)
C4—C5—C6—C11.2 (5)C14—C15—C16—C171.3 (7)
C2—C1—C6—C51.8 (5)C15—C16—C17—C181.4 (6)
C8—C1—C6—C5178.6 (3)C19—N3—C18—C17176.6 (4)
C9—N1—C8—O21.7 (5)C19—N3—C18—C131.2 (4)
C9—N1—C8—C1175.9 (3)C16—C17—C18—N3177.1 (4)
C2—C1—C8—O2155.1 (3)C16—C17—C18—C130.3 (6)
C6—C1—C8—O224.5 (5)C14—C13—C18—N3178.8 (3)
C2—C1—C8—N127.4 (4)C12—C13—C18—N31.0 (4)
C6—C1—C8—N1153.0 (3)C14—C13—C18—C170.8 (5)
C10—N2—C9—N1179.4 (3)C12—C13—C18—C17177.0 (3)
C10—N2—C9—S10.9 (4)C13—C12—C19—N30.3 (4)
C8—N1—C9—N23.0 (5)C11—C12—C19—N3178.8 (3)
C8—N1—C9—S1176.7 (2)C18—N3—C19—C120.9 (4)
C9—N2—C10—C20147.0 (3)N2—C10—C20—O321.3 (4)
C9—N2—C10—C1191.2 (4)C11—C10—C20—O3101.1 (4)
N2—C10—C11—C1254.7 (4)N2—C10—C20—O4161.6 (3)
C20—C10—C11—C1265.5 (3)C11—C10—C20—O476.0 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C10—H10···S10.982.643.059 (3)106
N2—H2A···O20.861.952.628 (3)135
N2—H2A···O30.862.372.680 (3)102
N1—H1A···O3i0.862.132.955 (3)160
N3—H3A···S1ii0.862.643.434 (3)154
O4—H4···S1iii0.822.403.219 (3)173
C2—H2···O3i0.932.442.986 (4)118
C3—H3···O2i0.932.533.332 (4)145
Symmetry codes: (i) x, y+2, z1/2; (ii) x+3/2, y+3/2, z+1/2; (iii) x, y+2, z+1/2.
 

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