The indole and indane moieties of the title molecule, C
18H
13NO, 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
CCDC reference: 200760
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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.
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-(1
H-indol-3-ylmethylene)indane-1-one
top
Crystal data top
C18H13NO | F(000) = 544 |
Mr = 259.29 | Dx = 1.313 Mg m−3 |
Orthorhombic, Pca21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2ac | Cell parameters from 25 reflections |
a = 12.3964 (17) Å | θ = 10–15° |
b = 4.961 (4) Å | µ = 0.08 mm−1 |
c = 21.330 (4) Å | T = 293 K |
V = 1311.7 (10) Å3 | Needle, brown |
Z = 4 | 0.40 × 0.20 × 0.05 mm |
Data collection top
Enraf-Nonius CAD-4 diffractometer | 848 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.026 |
Graphite monochromator | θmax = 25.0°, θmin = 3.3° |
ω–2θ scans | h = −1→14 |
Absorption correction: ψ scan (North et al., 1968) | k = −1→5 |
Tmin = 0.968, Tmax = 0.996 | l = −25→1 |
1686 measured reflections | 2 standard reflections every 120 min |
1244 independent reflections | intensity decay: none |
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) = 0.099 | w = 1/[σ2(Fo2) + (0.0239P)2 + 0.4636P] where P = (Fo2 + 2Fc2)/3 |
S = 1.19 | (Δ/σ)max < 0.001 |
1244 reflections | Δρmax = 0.15 e Å−3 |
182 parameters | Δρmin = −0.16 e Å−3 |
1 restraint | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction 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 | x | y | z | Uiso*/Ueq | |
N1 | 0.3003 (3) | −0.3288 (8) | 0.26664 (18) | 0.0496 (11) | |
H1 | 0.3620 | −0.4069 | 0.2700 | 0.060* | |
C2 | 0.2644 (3) | −0.1240 (9) | 0.3033 (2) | 0.0437 (12) | |
H2 | 0.3025 | −0.0483 | 0.3365 | 0.052* | |
C3 | 0.1633 (3) | −0.0448 (9) | 0.28429 (19) | 0.0373 (11) | |
C4 | 0.1344 (3) | −0.2175 (9) | 0.23230 (19) | 0.0358 (10) | |
C5 | 0.0428 (4) | −0.2454 (9) | 0.1956 (2) | 0.0473 (13) | |
H5 | −0.0162 | −0.1320 | 0.2013 | 0.057* | |
C6 | 0.0407 (4) | −0.4451 (10) | 0.1504 (3) | 0.0548 (14) | |
H6 | −0.0207 | −0.4675 | 0.1259 | 0.066* | |
C7 | 0.1301 (4) | −0.6150 (10) | 0.1409 (2) | 0.0528 (13) | |
H7 | 0.1273 | −0.7457 | 0.1096 | 0.063* | |
C8 | 0.2206 (4) | −0.5913 (10) | 0.1766 (2) | 0.0518 (14) | |
H8 | 0.2797 | −0.7039 | 0.1705 | 0.062* | |
C9 | 0.2215 (4) | −0.3919 (9) | 0.2228 (2) | 0.0397 (11) | |
C10 | 0.0959 (3) | 0.1672 (9) | 0.3083 (2) | 0.0394 (12) | |
H10 | 0.0336 | 0.2001 | 0.2852 | 0.047* | |
C11 | 0.0298 (4) | 0.5337 (9) | 0.3760 (2) | 0.0421 (12) | |
O11 | −0.0522 (2) | 0.5955 (7) | 0.34663 (16) | 0.0579 (10) | |
C12 | 0.0661 (4) | 0.6545 (10) | 0.4350 (2) | 0.0479 (13) | |
C13 | 0.0169 (5) | 0.8525 (10) | 0.4713 (3) | 0.0603 (15) | |
H13 | −0.0485 | 0.9287 | 0.4594 | 0.072* | |
C14 | 0.0683 (6) | 0.9320 (13) | 0.5257 (3) | 0.079 (2) | |
H14 | 0.0372 | 1.0643 | 0.5507 | 0.095* | |
C15 | 0.1641 (6) | 0.8191 (14) | 0.5431 (3) | 0.0804 (19) | |
H15 | 0.1968 | 0.8752 | 0.5801 | 0.096* | |
C16 | 0.2135 (5) | 0.6240 (12) | 0.5073 (3) | 0.0709 (18) | |
H16 | 0.2796 | 0.5515 | 0.5192 | 0.085* | |
C17 | 0.1622 (4) | 0.5378 (10) | 0.4526 (2) | 0.0478 (12) | |
C18 | 0.1981 (4) | 0.3262 (10) | 0.4065 (2) | 0.0460 (13) | |
H18A | 0.2665 | 0.3743 | 0.3875 | 0.055* | |
H18B | 0.2050 | 0.1516 | 0.4266 | 0.055* | |
C19 | 0.1089 (3) | 0.3258 (9) | 0.3590 (2) | 0.0389 (11) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.037 (2) | 0.050 (2) | 0.061 (3) | 0.0016 (19) | −0.005 (2) | −0.001 (3) |
C2 | 0.047 (3) | 0.042 (3) | 0.042 (3) | −0.005 (2) | −0.003 (2) | −0.002 (3) |
C3 | 0.031 (2) | 0.038 (3) | 0.043 (3) | 0.001 (2) | 0.000 (2) | 0.007 (2) |
C4 | 0.039 (2) | 0.036 (2) | 0.032 (2) | −0.003 (2) | −0.001 (2) | 0.002 (2) |
C5 | 0.049 (3) | 0.041 (3) | 0.051 (3) | −0.002 (3) | −0.009 (3) | −0.002 (3) |
C6 | 0.065 (3) | 0.048 (3) | 0.051 (3) | −0.006 (3) | −0.010 (3) | 0.004 (3) |
C7 | 0.075 (3) | 0.037 (3) | 0.046 (3) | −0.008 (3) | 0.004 (3) | −0.003 (2) |
C8 | 0.059 (3) | 0.044 (3) | 0.052 (3) | −0.004 (3) | 0.008 (3) | 0.002 (3) |
C9 | 0.046 (3) | 0.032 (2) | 0.041 (2) | −0.002 (2) | 0.004 (2) | 0.004 (3) |
C10 | 0.037 (2) | 0.040 (3) | 0.040 (3) | −0.009 (2) | −0.001 (2) | 0.004 (3) |
C11 | 0.033 (2) | 0.044 (3) | 0.049 (3) | −0.008 (2) | 0.002 (2) | 0.000 (3) |
O11 | 0.0371 (17) | 0.064 (2) | 0.072 (2) | 0.0023 (17) | −0.0036 (18) | −0.018 (2) |
C12 | 0.052 (3) | 0.046 (3) | 0.046 (3) | −0.014 (3) | 0.006 (3) | −0.005 (3) |
C13 | 0.078 (4) | 0.048 (3) | 0.055 (3) | −0.008 (3) | 0.021 (3) | −0.006 (3) |
C14 | 0.122 (6) | 0.057 (4) | 0.058 (4) | −0.017 (4) | 0.033 (4) | −0.014 (3) |
C15 | 0.132 (6) | 0.063 (4) | 0.046 (3) | −0.024 (4) | 0.000 (4) | −0.006 (4) |
C16 | 0.098 (5) | 0.065 (4) | 0.050 (3) | −0.018 (4) | −0.014 (4) | 0.013 (3) |
C17 | 0.067 (3) | 0.043 (3) | 0.033 (2) | −0.016 (3) | −0.003 (3) | 0.003 (2) |
C18 | 0.049 (3) | 0.045 (3) | 0.044 (3) | 0.001 (3) | −0.002 (2) | 0.004 (3) |
C19 | 0.036 (2) | 0.039 (3) | 0.042 (3) | −0.004 (2) | −0.001 (2) | 0.004 (3) |
Geometric parameters (Å, º) top
N1—C2 | 1.358 (6) | C10—H10 | 0.93 |
N1—C9 | 1.388 (5) | C11—O11 | 1.232 (5) |
N1—H1 | 0.86 | C11—C12 | 1.464 (6) |
C2—C3 | 1.375 (5) | C11—C19 | 1.469 (6) |
C2—H2 | 0.93 | C12—C17 | 1.376 (7) |
C3—C10 | 1.437 (6) | C12—C13 | 1.392 (7) |
C3—C4 | 1.446 (6) | C13—C14 | 1.380 (7) |
C4—C5 | 1.386 (6) | C13—H13 | 0.93 |
C4—C9 | 1.399 (6) | C14—C15 | 1.364 (8) |
C5—C6 | 1.383 (6) | C14—H14 | 0.93 |
C5—H5 | 0.93 | C15—C16 | 1.377 (9) |
C6—C7 | 1.407 (7) | C15—H15 | 0.93 |
C6—H6 | 0.93 | C16—C17 | 1.395 (7) |
C7—C8 | 1.362 (6) | C16—H16 | 0.93 |
C7—H7 | 0.93 | C17—C18 | 1.505 (7) |
C8—C9 | 1.396 (6) | C18—C19 | 1.500 (6) |
C8—H8 | 0.93 | C18—H18A | 0.97 |
C10—C19 | 1.348 (5) | C18—H18B | 0.97 |
| | | |
C2—N1—C9 | 109.1 (4) | O11—C11—C12 | 126.1 (4) |
C2—N1—H1 | 125.5 | O11—C11—C19 | 126.8 (4) |
C9—N1—H1 | 125.5 | C12—C11—C19 | 107.1 (4) |
N1—C2—C3 | 110.0 (4) | C17—C12—C13 | 121.6 (5) |
N1—C2—H2 | 125.0 | C17—C12—C11 | 109.2 (4) |
C3—C2—H2 | 125.0 | C13—C12—C11 | 129.2 (5) |
C2—C3—C10 | 129.3 (4) | C14—C13—C12 | 117.8 (6) |
C2—C3—C4 | 106.4 (4) | C14—C13—H13 | 121.1 |
C10—C3—C4 | 124.2 (4) | C12—C13—H13 | 121.1 |
C5—C4—C9 | 119.3 (4) | C15—C14—C13 | 120.8 (6) |
C5—C4—C3 | 134.0 (4) | C15—C14—H14 | 119.6 |
C9—C4—C3 | 106.7 (4) | C13—C14—H14 | 119.6 |
C6—C5—C4 | 118.7 (5) | C14—C15—C16 | 121.7 (6) |
C6—C5—H5 | 120.6 | C14—C15—H15 | 119.2 |
C4—C5—H5 | 120.6 | C16—C15—H15 | 119.2 |
C5—C6—C7 | 121.0 (5) | C15—C16—C17 | 118.4 (6) |
C5—C6—H6 | 119.5 | C15—C16—H16 | 120.8 |
C7—C6—H6 | 119.5 | C17—C16—H16 | 120.8 |
C8—C7—C6 | 121.1 (5) | C12—C17—C16 | 119.6 (5) |
C8—C7—H7 | 119.4 | C12—C17—C18 | 111.8 (4) |
C6—C7—H7 | 119.4 | C16—C17—C18 | 128.6 (5) |
C7—C8—C9 | 117.5 (5) | C19—C18—C17 | 102.9 (4) |
C7—C8—H8 | 121.2 | C19—C18—H18A | 111.2 |
C9—C8—H8 | 121.2 | C17—C18—H18A | 111.2 |
N1—C9—C8 | 129.9 (4) | C19—C18—H18B | 111.2 |
N1—C9—C4 | 107.8 (4) | C17—C18—H18B | 111.2 |
C8—C9—C4 | 122.3 (5) | H18A—C18—H18B | 109.1 |
C19—C10—C3 | 130.0 (4) | C10—C19—C11 | 121.9 (4) |
C19—C10—H10 | 115.0 | C10—C19—C18 | 129.2 (4) |
C3—C10—H10 | 115.0 | C11—C19—C18 | 108.9 (4) |
| | | |
C9—N1—C2—C3 | −1.0 (5) | C17—C12—C13—C14 | 0.8 (7) |
N1—C2—C3—C10 | −178.3 (4) | C11—C12—C13—C14 | 179.9 (5) |
N1—C2—C3—C4 | 0.8 (4) | C12—C13—C14—C15 | −0.2 (8) |
C2—C3—C4—C5 | 176.6 (5) | C13—C14—C15—C16 | 0.5 (9) |
C10—C3—C4—C5 | −4.2 (7) | C14—C15—C16—C17 | −1.4 (9) |
C2—C3—C4—C9 | −0.4 (5) | C13—C12—C17—C16 | −1.8 (7) |
C10—C3—C4—C9 | 178.8 (4) | C11—C12—C17—C16 | 179.0 (4) |
C9—C4—C5—C6 | −0.2 (6) | C13—C12—C17—C18 | 178.9 (5) |
C3—C4—C5—C6 | −177.0 (5) | C11—C12—C17—C18 | −0.3 (5) |
C4—C5—C6—C7 | −0.9 (7) | C15—C16—C17—C12 | 2.0 (8) |
C5—C6—C7—C8 | 1.2 (8) | C15—C16—C17—C18 | −178.8 (5) |
C6—C7—C8—C9 | −0.2 (7) | C12—C17—C18—C19 | −1.3 (5) |
C2—N1—C9—C8 | −178.1 (4) | C16—C17—C18—C19 | 179.5 (5) |
C2—N1—C9—C4 | 0.7 (5) | C3—C10—C19—C11 | −179.9 (4) |
C7—C8—C9—N1 | 177.7 (5) | C3—C10—C19—C18 | −0.7 (7) |
C7—C8—C9—C4 | −1.0 (6) | O11—C11—C19—C10 | −3.0 (7) |
C5—C4—C9—N1 | −177.7 (4) | C12—C11—C19—C10 | 176.7 (4) |
C3—C4—C9—N1 | −0.2 (5) | O11—C11—C19—C18 | 177.7 (4) |
C5—C4—C9—C8 | 1.2 (6) | C12—C11—C19—C18 | −2.6 (5) |
C3—C4—C9—C8 | 178.8 (4) | C17—C18—C19—C10 | −176.9 (4) |
C2—C3—C10—C19 | −7.3 (7) | C17—C18—C19—C11 | 2.3 (5) |
C4—C3—C10—C19 | 173.8 (4) | C11—C19—C10—H10 | 0.1 |
O11—C11—C12—C17 | −178.5 (5) | C18—C19—C10—H10 | 179.3 |
C19—C11—C12—C17 | 1.8 (5) | H13—C13—C12—C11 | −0.1 |
O11—C11—C12—C13 | 2.4 (8) | H10—C10—C3—C2 | 172.7 |
C19—C11—C12—C13 | −177.4 (5) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O11i | 0.86 | 2.16 | 2.829 (5) | 134 |
C18—H18A···O11ii | 0.97 | 2.42 | 3.371 (6) | 168 |
Symmetry codes: (i) x+1/2, −y, z; (ii) x+1/2, −y+1, z. |