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The indole and indane moieties of the title mol­ecule, C18H13NO, form a dihedral angle of 10.2 (2)°. In the crystal structure, symmetry-related mol­ecules are linked by intermolecular N—H...O and C—H...O hydrogen bonds to form infinite one-dimensional chains along the b axis. This chain structure is further stabilized by π–π and C—H...π interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802017774/ci6162sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802017774/ci6162Isup2.hkl
Contains datablock I

CCDC reference: 200760

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.043
  • wR factor = 0.099
  • Data-to-parameter ratio = 6.8

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes

REFLT_03 From the CIF: _diffrn_reflns_theta_max 24.97 From the CIF: _reflns_number_total 1244 Count of symmetry unique reflns 1182 Completeness (_total/calc) 105.25% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 62 Fraction of Friedel pairs measured 0.052 Are heavy atom types Z>Si present no ALERT: MoKa measured Friedel data cannot be used to determine absolute structure in a light-atom study EXCEPT under VERY special conditions. It is preferred that Friedel data is merged in such cases.

Computing details top

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: MolEN (Fair, 1990); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP97 (Zsolnai, 1997); software used to prepare material for publication: SHELXL97.

2-(1H-indol-3-ylmethylene)indane-1-one top
Crystal data top
C18H13NOF(000) = 544
Mr = 259.29Dx = 1.313 Mg m3
Orthorhombic, Pca21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2acCell parameters from 25 reflections
a = 12.3964 (17) Åθ = 10–15°
b = 4.961 (4) ŵ = 0.08 mm1
c = 21.330 (4) ÅT = 293 K
V = 1311.7 (10) Å3Needle, brown
Z = 40.40 × 0.20 × 0.05 mm
Data collection top
Enraf-Nonius CAD-4
diffractometer
848 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.026
Graphite monochromatorθmax = 25.0°, θmin = 3.3°
ω–2θ scansh = 114
Absorption correction: ψ scan
(North et al., 1968)
k = 15
Tmin = 0.968, Tmax = 0.996l = 251
1686 measured reflections2 standard reflections every 120 min
1244 independent reflections intensity decay: none
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043H-atom parameters constrained
wR(F2) = 0.099 w = 1/[σ2(Fo2) + (0.0239P)2 + 0.4636P]
where P = (Fo2 + 2Fc2)/3
S = 1.19(Δ/σ)max < 0.001
1244 reflectionsΔρmax = 0.15 e Å3
182 parametersΔρmin = 0.16 e Å3
1 restraintExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0077 (13)
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
N10.3003 (3)0.3288 (8)0.26664 (18)0.0496 (11)
H10.36200.40690.27000.060*
C20.2644 (3)0.1240 (9)0.3033 (2)0.0437 (12)
H20.30250.04830.33650.052*
C30.1633 (3)0.0448 (9)0.28429 (19)0.0373 (11)
C40.1344 (3)0.2175 (9)0.23230 (19)0.0358 (10)
C50.0428 (4)0.2454 (9)0.1956 (2)0.0473 (13)
H50.01620.13200.20130.057*
C60.0407 (4)0.4451 (10)0.1504 (3)0.0548 (14)
H60.02070.46750.12590.066*
C70.1301 (4)0.6150 (10)0.1409 (2)0.0528 (13)
H70.12730.74570.10960.063*
C80.2206 (4)0.5913 (10)0.1766 (2)0.0518 (14)
H80.27970.70390.17050.062*
C90.2215 (4)0.3919 (9)0.2228 (2)0.0397 (11)
C100.0959 (3)0.1672 (9)0.3083 (2)0.0394 (12)
H100.03360.20010.28520.047*
C110.0298 (4)0.5337 (9)0.3760 (2)0.0421 (12)
O110.0522 (2)0.5955 (7)0.34663 (16)0.0579 (10)
C120.0661 (4)0.6545 (10)0.4350 (2)0.0479 (13)
C130.0169 (5)0.8525 (10)0.4713 (3)0.0603 (15)
H130.04850.92870.45940.072*
C140.0683 (6)0.9320 (13)0.5257 (3)0.079 (2)
H140.03721.06430.55070.095*
C150.1641 (6)0.8191 (14)0.5431 (3)0.0804 (19)
H150.19680.87520.58010.096*
C160.2135 (5)0.6240 (12)0.5073 (3)0.0709 (18)
H160.27960.55150.51920.085*
C170.1622 (4)0.5378 (10)0.4526 (2)0.0478 (12)
C180.1981 (4)0.3262 (10)0.4065 (2)0.0460 (13)
H18A0.26650.37430.38750.055*
H18B0.20500.15160.42660.055*
C190.1089 (3)0.3258 (9)0.3590 (2)0.0389 (11)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.037 (2)0.050 (2)0.061 (3)0.0016 (19)0.005 (2)0.001 (3)
C20.047 (3)0.042 (3)0.042 (3)0.005 (2)0.003 (2)0.002 (3)
C30.031 (2)0.038 (3)0.043 (3)0.001 (2)0.000 (2)0.007 (2)
C40.039 (2)0.036 (2)0.032 (2)0.003 (2)0.001 (2)0.002 (2)
C50.049 (3)0.041 (3)0.051 (3)0.002 (3)0.009 (3)0.002 (3)
C60.065 (3)0.048 (3)0.051 (3)0.006 (3)0.010 (3)0.004 (3)
C70.075 (3)0.037 (3)0.046 (3)0.008 (3)0.004 (3)0.003 (2)
C80.059 (3)0.044 (3)0.052 (3)0.004 (3)0.008 (3)0.002 (3)
C90.046 (3)0.032 (2)0.041 (2)0.002 (2)0.004 (2)0.004 (3)
C100.037 (2)0.040 (3)0.040 (3)0.009 (2)0.001 (2)0.004 (3)
C110.033 (2)0.044 (3)0.049 (3)0.008 (2)0.002 (2)0.000 (3)
O110.0371 (17)0.064 (2)0.072 (2)0.0023 (17)0.0036 (18)0.018 (2)
C120.052 (3)0.046 (3)0.046 (3)0.014 (3)0.006 (3)0.005 (3)
C130.078 (4)0.048 (3)0.055 (3)0.008 (3)0.021 (3)0.006 (3)
C140.122 (6)0.057 (4)0.058 (4)0.017 (4)0.033 (4)0.014 (3)
C150.132 (6)0.063 (4)0.046 (3)0.024 (4)0.000 (4)0.006 (4)
C160.098 (5)0.065 (4)0.050 (3)0.018 (4)0.014 (4)0.013 (3)
C170.067 (3)0.043 (3)0.033 (2)0.016 (3)0.003 (3)0.003 (2)
C180.049 (3)0.045 (3)0.044 (3)0.001 (3)0.002 (2)0.004 (3)
C190.036 (2)0.039 (3)0.042 (3)0.004 (2)0.001 (2)0.004 (3)
Geometric parameters (Å, º) top
N1—C21.358 (6)C10—H100.93
N1—C91.388 (5)C11—O111.232 (5)
N1—H10.86C11—C121.464 (6)
C2—C31.375 (5)C11—C191.469 (6)
C2—H20.93C12—C171.376 (7)
C3—C101.437 (6)C12—C131.392 (7)
C3—C41.446 (6)C13—C141.380 (7)
C4—C51.386 (6)C13—H130.93
C4—C91.399 (6)C14—C151.364 (8)
C5—C61.383 (6)C14—H140.93
C5—H50.93C15—C161.377 (9)
C6—C71.407 (7)C15—H150.93
C6—H60.93C16—C171.395 (7)
C7—C81.362 (6)C16—H160.93
C7—H70.93C17—C181.505 (7)
C8—C91.396 (6)C18—C191.500 (6)
C8—H80.93C18—H18A0.97
C10—C191.348 (5)C18—H18B0.97
C2—N1—C9109.1 (4)O11—C11—C12126.1 (4)
C2—N1—H1125.5O11—C11—C19126.8 (4)
C9—N1—H1125.5C12—C11—C19107.1 (4)
N1—C2—C3110.0 (4)C17—C12—C13121.6 (5)
N1—C2—H2125.0C17—C12—C11109.2 (4)
C3—C2—H2125.0C13—C12—C11129.2 (5)
C2—C3—C10129.3 (4)C14—C13—C12117.8 (6)
C2—C3—C4106.4 (4)C14—C13—H13121.1
C10—C3—C4124.2 (4)C12—C13—H13121.1
C5—C4—C9119.3 (4)C15—C14—C13120.8 (6)
C5—C4—C3134.0 (4)C15—C14—H14119.6
C9—C4—C3106.7 (4)C13—C14—H14119.6
C6—C5—C4118.7 (5)C14—C15—C16121.7 (6)
C6—C5—H5120.6C14—C15—H15119.2
C4—C5—H5120.6C16—C15—H15119.2
C5—C6—C7121.0 (5)C15—C16—C17118.4 (6)
C5—C6—H6119.5C15—C16—H16120.8
C7—C6—H6119.5C17—C16—H16120.8
C8—C7—C6121.1 (5)C12—C17—C16119.6 (5)
C8—C7—H7119.4C12—C17—C18111.8 (4)
C6—C7—H7119.4C16—C17—C18128.6 (5)
C7—C8—C9117.5 (5)C19—C18—C17102.9 (4)
C7—C8—H8121.2C19—C18—H18A111.2
C9—C8—H8121.2C17—C18—H18A111.2
N1—C9—C8129.9 (4)C19—C18—H18B111.2
N1—C9—C4107.8 (4)C17—C18—H18B111.2
C8—C9—C4122.3 (5)H18A—C18—H18B109.1
C19—C10—C3130.0 (4)C10—C19—C11121.9 (4)
C19—C10—H10115.0C10—C19—C18129.2 (4)
C3—C10—H10115.0C11—C19—C18108.9 (4)
C9—N1—C2—C31.0 (5)C17—C12—C13—C140.8 (7)
N1—C2—C3—C10178.3 (4)C11—C12—C13—C14179.9 (5)
N1—C2—C3—C40.8 (4)C12—C13—C14—C150.2 (8)
C2—C3—C4—C5176.6 (5)C13—C14—C15—C160.5 (9)
C10—C3—C4—C54.2 (7)C14—C15—C16—C171.4 (9)
C2—C3—C4—C90.4 (5)C13—C12—C17—C161.8 (7)
C10—C3—C4—C9178.8 (4)C11—C12—C17—C16179.0 (4)
C9—C4—C5—C60.2 (6)C13—C12—C17—C18178.9 (5)
C3—C4—C5—C6177.0 (5)C11—C12—C17—C180.3 (5)
C4—C5—C6—C70.9 (7)C15—C16—C17—C122.0 (8)
C5—C6—C7—C81.2 (8)C15—C16—C17—C18178.8 (5)
C6—C7—C8—C90.2 (7)C12—C17—C18—C191.3 (5)
C2—N1—C9—C8178.1 (4)C16—C17—C18—C19179.5 (5)
C2—N1—C9—C40.7 (5)C3—C10—C19—C11179.9 (4)
C7—C8—C9—N1177.7 (5)C3—C10—C19—C180.7 (7)
C7—C8—C9—C41.0 (6)O11—C11—C19—C103.0 (7)
C5—C4—C9—N1177.7 (4)C12—C11—C19—C10176.7 (4)
C3—C4—C9—N10.2 (5)O11—C11—C19—C18177.7 (4)
C5—C4—C9—C81.2 (6)C12—C11—C19—C182.6 (5)
C3—C4—C9—C8178.8 (4)C17—C18—C19—C10176.9 (4)
C2—C3—C10—C197.3 (7)C17—C18—C19—C112.3 (5)
C4—C3—C10—C19173.8 (4)C11—C19—C10—H100.1
O11—C11—C12—C17178.5 (5)C18—C19—C10—H10179.3
C19—C11—C12—C171.8 (5)H13—C13—C12—C110.1
O11—C11—C12—C132.4 (8)H10—C10—C3—C2172.7
C19—C11—C12—C13177.4 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O11i0.862.162.829 (5)134
C18—H18A···O11ii0.972.423.371 (6)168
Symmetry codes: (i) x+1/2, y, z; (ii) x+1/2, y+1, z.
 

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