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The title compound, C10H9NO2, was isolated and characterized from an EtOAc extract of marine Streptomyces sp. 060524. All atoms, except the methyl H atoms, are nearly coplanar. There is an inter­molecular N—H...O hydrogen bond in the crystal stucture. The compound is cytotoxic against K562 human chronic leukaemia.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805012109/bt6646sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805012109/bt6646Isup2.hkl
Contains datablock I

CCDC reference: 274336

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.056
  • wR factor = 0.152
  • Data-to-parameter ratio = 14.4

checkCIF/PLATON results

No syntax errors found



Alert level C CELLV02_ALERT_1_C The supplied cell volume s.u. differs from that calculated from the cell parameter s.u.'s by > 2 Calculated cell volume su = 8.88 Cell volume su given = 6.00 RINTA01_ALERT_3_C The value of Rint is greater than 0.10 Rint given 0.146 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.15 PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98 PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT230_ALERT_2_C Hirshfeld Test Diff for C7 - C8 .. 6.16 su
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 8 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 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 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 (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); 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.

Methyl indole-3-carboxylate top
Crystal data top
C10H9NO2F(000) = 736
Mr = 175.18Dx = 1.347 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 21.382 (4) ÅCell parameters from 1009 reflections
b = 7.4070 (15) Åθ = 2.9–26.5°
c = 13.372 (3) ŵ = 0.10 mm1
β = 125.34 (3)°T = 298 K
V = 1727.6 (6) Å3Prism, colourless
Z = 80.45 × 0.41 × 0.38 mm
Data collection top
Siemens SMART CCD area-detector
diffractometer
1752 independent reflections
Radiation source: fine-focus sealed tube1315 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.146
φ and ω scansθmax = 26.5°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 2626
Tmin = 0.959, Tmax = 0.965k = 95
5009 measured reflectionsl = 1616
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)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.152H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0677P)2 + 0.0691P]
where P = (Fo2 + 2Fc2)/3
1752 reflections(Δ/σ)max < 0.001
122 parametersΔρmax = 0.34 e Å3
1 restraintΔρmin = 0.33 e Å3
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
xyzUiso*/Ueq
O10.23931 (6)0.28869 (16)0.36724 (11)0.0529 (4)
O20.35102 (5)0.43096 (16)0.49706 (10)0.0534 (4)
N10.23271 (7)0.90625 (17)0.35139 (12)0.0478 (4)
C10.16367 (8)0.6504 (2)0.28083 (12)0.0403 (4)
C20.15931 (8)0.8388 (2)0.27359 (13)0.0433 (4)
C30.09050 (9)0.9314 (3)0.19884 (15)0.0564 (5)
H30.08881.05690.19520.068*
C40.02488 (10)0.8286 (3)0.13045 (17)0.0658 (5)
H40.02230.88590.07950.079*
C50.02772 (9)0.6419 (3)0.13603 (16)0.0626 (5)
H50.01780.57700.08890.075*
C60.09592 (8)0.5490 (3)0.20931 (14)0.0517 (4)
H60.09700.42340.21130.062*
C70.24359 (7)0.6066 (2)0.36797 (12)0.0400 (4)
C80.28203 (9)0.7678 (2)0.40701 (15)0.0461 (4)
H80.33470.77980.46390.055*
C90.27562 (8)0.4288 (2)0.40758 (13)0.0401 (4)
C100.38748 (10)0.2590 (2)0.54184 (19)0.0615 (5)
H10A0.36100.18970.56710.092*
H10B0.43980.27620.61040.092*
H10C0.38620.19580.47800.092*
H10.2455 (10)1.0248 (15)0.3644 (18)0.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0529 (6)0.0330 (7)0.0656 (7)0.0009 (5)0.0302 (6)0.0007 (5)
O20.0436 (6)0.0418 (7)0.0631 (7)0.0047 (4)0.0242 (5)0.0034 (5)
N10.0514 (7)0.0300 (8)0.0571 (8)0.0024 (5)0.0286 (6)0.0030 (6)
C10.0463 (8)0.0319 (9)0.0442 (7)0.0009 (6)0.0271 (6)0.0008 (6)
C20.0487 (8)0.0366 (10)0.0463 (7)0.0021 (6)0.0284 (7)0.0010 (6)
C30.0577 (9)0.0429 (10)0.0642 (10)0.0129 (7)0.0327 (8)0.0066 (8)
C40.0484 (9)0.0645 (15)0.0713 (11)0.0126 (9)0.0270 (8)0.0084 (10)
C50.0435 (8)0.0579 (13)0.0695 (10)0.0033 (8)0.0228 (8)0.0020 (10)
C60.0490 (8)0.0390 (10)0.0597 (9)0.0052 (7)0.0272 (7)0.0010 (7)
C70.0434 (7)0.0313 (8)0.0449 (8)0.0018 (6)0.0252 (6)0.0022 (6)
C80.0434 (7)0.0392 (10)0.0520 (8)0.0009 (6)0.0254 (7)0.0018 (6)
C90.0421 (7)0.0354 (8)0.0451 (7)0.0004 (6)0.0266 (6)0.0009 (6)
C100.0506 (9)0.0546 (13)0.0710 (11)0.0151 (7)0.0304 (9)0.0138 (8)
Geometric parameters (Å, º) top
O1—C91.2189 (18)C4—C51.384 (3)
O2—C91.3415 (18)C4—H40.9300
O2—C101.4312 (19)C5—C61.381 (3)
N1—C81.345 (2)C5—H50.9300
N1—C21.3808 (19)C6—H60.9300
N1—H10.906 (10)C7—C81.370 (2)
C1—C21.398 (2)C7—C91.437 (2)
C1—C61.406 (2)C8—H80.9300
C1—C71.4421 (19)C10—H10A0.9600
C2—C31.390 (2)C10—H10B0.9600
C3—C41.379 (3)C10—H10C0.9600
C3—H30.9300
C9—O2—C10116.44 (13)C5—C6—C1117.76 (18)
C8—N1—C2109.06 (13)C5—C6—H6121.1
C8—N1—H1125.4 (12)C1—C6—H6121.1
C2—N1—H1125.5 (12)C8—C7—C9127.25 (14)
C2—C1—C6119.04 (13)C8—C7—C1106.32 (13)
C2—C1—C7106.33 (12)C9—C7—C1126.41 (13)
C6—C1—C7134.64 (15)N1—C8—C7110.36 (15)
N1—C2—C3129.18 (16)N1—C8—H8124.8
N1—C2—C1107.93 (12)C7—C8—H8124.8
C3—C2—C1122.89 (14)O1—C9—O2122.29 (14)
C4—C3—C2116.87 (18)O1—C9—C7124.85 (14)
C4—C3—H3121.6O2—C9—C7112.85 (13)
C2—C3—H3121.6O2—C10—H10A109.5
C3—C4—C5121.32 (15)O2—C10—H10B109.5
C3—C4—H4119.3H10A—C10—H10B109.5
C5—C4—H4119.3O2—C10—H10C109.5
C6—C5—C4122.12 (16)H10A—C10—H10C109.5
C6—C5—H5118.9H10B—C10—H10C109.5
C4—C5—H5118.9
C8—N1—C2—C3179.28 (14)C2—C1—C7—C80.25 (14)
C8—N1—C2—C10.50 (15)C6—C1—C7—C8179.87 (15)
C6—C1—C2—N1179.86 (12)C2—C1—C7—C9178.33 (13)
C7—C1—C2—N10.46 (12)C6—C1—C7—C91.3 (2)
C6—C1—C2—C30.35 (18)C2—N1—C8—C70.34 (18)
C7—C1—C2—C3179.34 (13)C9—C7—C8—N1178.62 (12)
N1—C2—C3—C4179.58 (14)C1—C7—C8—N10.05 (17)
C1—C2—C3—C40.2 (2)C10—O2—C9—O11.1 (2)
C2—C3—C4—C50.2 (2)C10—O2—C9—C7179.98 (12)
C3—C4—C5—C60.3 (3)C8—C7—C9—O1177.58 (14)
C4—C5—C6—C10.8 (2)C1—C7—C9—O14.1 (2)
C2—C1—C6—C50.84 (19)C8—C7—C9—O23.5 (2)
C7—C1—C6—C5178.74 (14)C1—C7—C9—O2174.74 (11)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.91 (1)1.96 (1)2.8381 (18)162 (2)
Symmetry code: (i) x, y+1, z.
 

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