Download citation
Download citation
link to html
1-Methyl­indole-3-carbox­aldehyde oxime, C10H10N2O, (I),and (E)-5-methoxy-1-methyl­indole-3-carbox­aldehyde oxime, C11H12N2O2, (II), were ex­amined structurally to ascertain the geometry of the hydroxy­imino function relative to the indole core. Oxime (I) exhibits cis geometry and there are two mol­ecules in the asymmetric unit. In contrast, oxime (II) exhibits trans geometry and has four mol­ecules in the asymmetric unit, with the geometry of the 5-methoxy group in one mol­ecule differing from that in the other three. Both crystal structures are maintained by hydrogen bonding with no π-stacking of the indole moiety present.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100005795/gd1087sup1.cif
Contains datablocks global, I, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100005795/gd1087Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100005795/gd1087IIsup3.hkl
Contains datablock Oxime_II

CCDC references: 158247; 158248

Comment top

Oxime derivatives (RR'CHN—OH) are often the source of iminoxy radicals (RR'CHN—O.) when oxidized chemically (Thomas, 1964), enzymatically (Lagercrantz, 1988) or by radical species (Brokenshire et al., 1972). Based on electron-spin-resonance coupling constants of iminoxy radicals derived from lkyl/aryl oximes (which fall in a narrow range, aN \sim28 to 32 G), these radicals were originally characterized as σ radicals (Gilbert & Norman, 1966). However, the impact of structure on stabilities of iminoxy radicals became apparent when the bond dissociation energies (BDEs) for the O—H bonds in ketoximes were weakened dramatically by both resonance stabilization (implying that iminoxy radicals were acting as π radicals) and by increased steric congestion in the region of the hydroxyimino functionality (Bordwell & Zhang, 1995). The RR'CHN—O. radical is a putative intermediate in the oxidation of aryl oximes to nitric oxides by the oxidase and mono-oxygenase activities of cytochrome P450s (Jousserandot et al., 1998). We report herein the structural characterization of the 1-methylindole-3-carboxyaldehyde oxime, (I), and the corresponding 5-methoxy derivative, (II), the geometry of which may influence the stability of their iminoxy radicals.

Oxime (I) contains two molecules (A and B) in the asymmetric unit. Fig. 1 presents a displacement ellipsoid plot of the labelled asymmetric unit. A pairwise comparison between these two molecules shows there to be no significant differences in their bond lengths or angles. Pairwise comparisons of the torsion angles show one significant difference between the molecules; the C7A—C6A—N9A—C10A torsion angle is 179.9 (4)°, while the C7B—C6B—N9B—C10B angle is 177.8 (4)°. The indole moiety in both molecules exhibits a high degree of planarity with overall root-mean-square deviations (rmsd) for the ring atoms of 0.0069 and 0.0082 Å for molecules A and B, respectively. The six- and five-membered rings of the indole groups are ostensibly planar with each other. The oxime moieties are also planar, with rmsd values of 0.0011 Å for molecule A and 0.0086 Å for molecule B. These oxime planes are not coplanar with the five-membered rings of the indole group, deviating by 15.82 and 14.96° for molecules, A and B, respectively. The oxime groups of both molecules have cis geometries for their O15 atoms, relative to their indole groups, and their deviations from planarity with the five-membered rings remove possible steric hindrances that would otherwise arise from this geometry.

Oxime (II) contains four molecules (A', B', C' and D') in the asymmetric unit. Minimal similarity restraints in SHELXL (Sheldrick, 1997) were applied to all atoms within these molecules with the exception of the methyl carbon of the 5-methoxy groups. Fig. 2 shows a displacement ellipsoid plot of the molecules of the asymmetric unit with labelling for molecule A' only, for ease of identification. Comparison of all four molecules shows that there are no differences for most of the corresponding bond lengths and angles, with a few notable exceptions. The methyl carbon of the 5- methoxy group of molecule A' is rotated towards the C8A atom side of the indole six-membered ring, while the remaining three methyl carbons are rotated towards their C4 atom side, resulting in significant differences in bond lengths between C1A—O2A and the other methyl C—O bonds of the methoxy groups (Table 3). The C1A—O2A bond is significantly shorter than that usually associated with a methyl C—O bond in a methoxy group attached to an aromatic ring (1.424 Å; Allen et al., 1987). Additionally, the C4A—C5A bond of the indole group is significantly shorter than the equivalent bond in the other three molecules. The bond angles associated with the methoxy group show significant differences. Unexpectedly, it is molecule B' that shows differences for the angle C3B—O2B—C1B when compared with molecules A' and D'. The methoxy groups of all four molecules are asymmetrically positioned on their respective six-membered rings. The larger of the two angles arises from distortion of the methyl group away from its ring (Table 3 and Fig. 2). The degree of asymmetry is least for molecule A', when compared with the other three molecules, and might emanate from the overall difference in geometry of its methoxy group. Other bond-angle differences exist between the four molecules, as shown in Table 3.

A number of significant differences exist between comparable torsion angles in the four molecules, many arising as a result of the difference in juxtaposition of the methoxy group in molecule A' with respect to its indole ring, in contrast to its position in the other three molecules. Further torsion-angle differences in these molecules can be implied from the least-squares deviations of the atoms in the different molecules from their indole ring planes. A table of this data is provided in the deposited material.

The different positions of the oxime groups in oxime (II) are also illustrated by the angles between their planes and the planes of the adjacent five-membered rings. These relative angles are 4.46 (3), 0.82 (3), 4.86 (3) and 3.68 (3)° for molecules A', B', C' and D', respectively, all indicating a passing degree of planarity with the rest of the molecule for these groups with trans geometry. From these values, molecule B' differs significantly in geometry from the other three molecules, but D' also differs significantly from A' and C'. However, these values are all significantly lower than those for the two molecules of oxime (I), illustrating again the need to remove steric hindrance from around the oxime in the molecules with cis geometries.

A detailed analysis of the geometries associated with the oxime moiety reveals that the C13 atom is significantly asymmetrically positioned off the five-membered ring in both oximes (I) and (II). This asymmetry is directly related to the geometry of the oxime moiety, notably whether it is cis or trans relative to the indole ring, and to the rotamer state of the oxime relative to the ring. In oxime (I), where the oxime moiety is cis to the indole ring, the rotation of the group is such that the N14 atom is towards atom C11. This juxtapositioning causes all the C7—C12—C13 angles to be smaller than the C11— C12—C13 angles. For oxime (II), the N14 atom is rotated towards the C7 side of the five-membered ring structure, and this results in the asymmetry being the opposite for the four molecules to that in the oxime (I) molecule. The need to reduce steric interaction in the cis geometry oxime (I) opens out the C12—C13— N14 angles of molecules A and B compared with the trans geometry of oxime (II). In contrast, all six independent molecules of oximes (I) and (II) have C13—N14—O15 angles of \sim110.5°. There are potential steric interactions in the cis geometry of oxime (I) between the oxime O atom and the ring. However, these are removed by the twist of the oxime groups away from planarity with the indole rings detailed earlier. The C13—N14 and N14—O15 bond lengths of the cis-geometry oxime (I) are, in the majority of comparisons, significantly shorter than the related bond lengths in the trans conformation in oxime (II) (Tables 1 and 3). These differences could also result from the cis/trans nature of the oxime group in these structures, but might reflect something of the electronic effect of adding a methoxy substituent to the indole ring.

The crystal structure of oxime (I) is maintained by hydrogen bonding, relating one molecule of the asymmetric unit to the other molecules of a symmetry-related asymmetric unit (Table 2). In contrast, while the structure of oxime (II) is also maintained by hydrogen bonding, the arrangement of hydrogen bonds within and between asymmetric units is noticeably different. Here, molecules A' and B' pseudo-heterodimerize across their oxime groups, while molecules C' and D' homodimerize to their own centrosymmetrically related mates. Both crystal structures exhibit a network of hydrogen bonds linking the molecules together, but there is no evidence of π-stacking arising from interactions between the indole rings.

Experimental top

Both oximes (I) (Hiremath et al., 1984) and (II) were prepared from commercially available indoles by N-methylation and formylation, followed by reaction with hydroxylamine. Crystals of (I) were grown by slow evaporation from methanol at room temperature, while crystals of (II) were also grown from methanol at room temperature but after initial nucleation were cooled to complete their growth at 277 K.

Refinement top

All H atoms for both crystal structures were initially located in differences maps, but were then placed geometrically in riding positions and refined isotropically with Uiso set to 1.2Ueq of the associated atom.

Computing details top

For both compounds, data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: CAD77 and CADRAL (Korber, 1982), and CADSHEL (Cooper, 1990); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of oxime (I) drawn with ellipsoids at the 30% probability level. Molecules A and B are marked, and the numbering scheme used in the text is shown for molecule A (ORTEP-3; Farrugia, 1997).
[Figure 2] Fig. 2. The asymmetric unit of oxime (II) drawn with ellipsoids at the 30% probability level. Molecules A', B', C' and D' are marked, and the numbering scheme used in the text is shown for molecule A' (ORTEP-3; Farrugia, 1997).
(I) 1-Methylindole-3-carboxyaldehyde oxime top
Crystal data top
C10H10N2OF(000) = 368
Mr = 174.20Dx = 1.288 Mg m3
Monoclinic, P21Cu Kα radiation, λ = 1.54180 Å
a = 13.462 (4) ÅCell parameters from 25 reflections
b = 5.079 (4) Åθ = 11.3–38.7°
c = 14.127 (4) ŵ = 0.69 mm1
β = 111.53 (4)°T = 293 K
V = 898.4 (8) Å3Needle, colourless
Z = 40.30 × 0.20 × 0.15 mm
Data collection top
Enraf-Nonius CAD-4
diffractometer
Rint = 0.052
Radiation source: fine-focus sealed tubeθmax = 74.2°, θmin = 3.9°
Graphite monochromatorh = 016
ω–2θ scansk = 60
3706 measured reflectionsl = 1716
2045 independent reflections3 standard reflections every 200 reflections
1039 reflections with I > 2σ(I) 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)] = 0.049H-atom parameters constrained
wR(F2) = 0.129Calculated w = 1/[σ2(Fo2) + (0.0453P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.001
2045 reflectionsΔρmax = 0.17 e Å3
240 parametersΔρmin = 0.20 e Å3
1 restraintExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0043 (7)
Crystal data top
C10H10N2OV = 898.4 (8) Å3
Mr = 174.20Z = 4
Monoclinic, P21Cu Kα radiation
a = 13.462 (4) ŵ = 0.69 mm1
b = 5.079 (4) ÅT = 293 K
c = 14.127 (4) Å0.30 × 0.20 × 0.15 mm
β = 111.53 (4)°
Data collection top
Enraf-Nonius CAD-4
diffractometer
Rint = 0.052
3706 measured reflections3 standard reflections every 200 reflections
2045 independent reflections intensity decay: none
1039 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0491 restraint
wR(F2) = 0.129H-atom parameters constrained
S = 1.00Δρmax = 0.17 e Å3
2045 reflectionsΔρmin = 0.20 e Å3
240 parameters
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
C3A0.5915 (4)0.0522 (12)0.4021 (4)0.0574 (16)
H3A0.61740.18590.44980.069*
C4A0.5035 (5)0.0968 (12)0.4003 (4)0.0592 (16)
H4A0.47270.06120.44810.071*
C5A0.4612 (4)0.2920 (11)0.3312 (4)0.0521 (14)
H5A0.40190.38810.33000.062*
C6A0.5111 (4)0.3404 (10)0.2627 (3)0.0430 (12)
C7A0.5993 (4)0.1984 (11)0.2623 (3)0.0422 (12)
C8A0.6398 (4)0.0019 (11)0.3337 (3)0.0495 (14)
H8A0.69870.09980.33490.059*
N9A0.4862 (3)0.5222 (9)0.1848 (3)0.0480 (11)
C10A0.3985 (4)0.7108 (13)0.1589 (4)0.0634 (16)
H10A0.33180.61800.13560.076*
H10B0.40150.82580.10610.076*
H10C0.40460.81280.21800.076*
C11A0.5579 (4)0.4987 (12)0.1386 (4)0.0511 (14)
H11A0.55820.60180.08430.061*
C12A0.6292 (4)0.3043 (11)0.1822 (4)0.0446 (12)
C13A0.7159 (4)0.2069 (12)0.1558 (4)0.0541 (14)
H13A0.74190.04290.18300.065*
N14A0.7636 (4)0.3104 (10)0.1005 (3)0.0555 (12)
O15A0.7183 (3)0.5535 (8)0.0633 (3)0.0619 (11)
H15A0.75470.62820.03590.074*
C3B0.2078 (5)0.0388 (13)0.4410 (4)0.0666 (18)
H3B0.25020.17420.47930.080*
C4B0.1470 (5)0.1116 (14)0.4822 (4)0.0633 (18)
H4B0.15020.07580.54780.076*
C5B0.0828 (4)0.3106 (12)0.4281 (4)0.0566 (15)
H5B0.04260.41100.45590.068*
C6B0.0796 (4)0.3584 (11)0.3296 (4)0.0470 (14)
C7B0.1405 (4)0.2096 (11)0.2868 (3)0.0422 (12)
C8B0.2059 (4)0.0100 (12)0.3445 (4)0.0552 (15)
H8B0.24780.08910.31820.066*
N9B0.0238 (3)0.5404 (9)0.2585 (3)0.0494 (11)
C10B0.0516 (4)0.7270 (13)0.2715 (4)0.0624 (17)
H10D0.11320.63450.27280.075*
H10E0.07280.84980.21600.075*
H10F0.01860.82030.33440.075*
C11B0.0479 (4)0.5174 (12)0.1741 (4)0.0483 (13)
H11B0.01990.62160.11620.058*
C12B0.1203 (4)0.3157 (12)0.1870 (3)0.0442 (12)
C13B0.1646 (4)0.2138 (12)0.1169 (4)0.0532 (14)
H13B0.19410.04670.13340.064*
N14B0.1714 (3)0.3096 (9)0.0351 (3)0.0528 (12)
O15B0.1212 (3)0.5558 (8)0.0115 (3)0.0604 (11)
H15B0.14020.63070.03040.073*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C3A0.073 (4)0.050 (4)0.055 (3)0.000 (3)0.030 (3)0.008 (3)
C4A0.072 (4)0.060 (4)0.056 (3)0.009 (4)0.036 (3)0.006 (3)
C5A0.063 (3)0.048 (4)0.057 (3)0.001 (3)0.035 (3)0.008 (3)
C6A0.055 (3)0.035 (3)0.042 (3)0.002 (3)0.022 (2)0.002 (3)
C7A0.049 (3)0.037 (3)0.043 (3)0.005 (3)0.020 (2)0.001 (3)
C8A0.060 (3)0.047 (4)0.047 (3)0.001 (3)0.025 (3)0.005 (3)
N9A0.056 (3)0.040 (3)0.050 (2)0.009 (3)0.021 (2)0.001 (2)
C10A0.061 (4)0.048 (4)0.078 (4)0.009 (3)0.022 (3)0.004 (3)
C11A0.062 (3)0.046 (4)0.050 (3)0.003 (3)0.026 (3)0.000 (3)
C12A0.057 (3)0.037 (3)0.045 (3)0.000 (3)0.026 (3)0.004 (3)
C13A0.071 (4)0.043 (3)0.055 (3)0.001 (3)0.032 (3)0.004 (3)
N14A0.069 (3)0.051 (3)0.053 (3)0.004 (3)0.030 (2)0.008 (3)
O15A0.083 (3)0.052 (3)0.067 (2)0.006 (2)0.047 (2)0.005 (2)
C3B0.070 (4)0.066 (5)0.058 (3)0.006 (4)0.017 (3)0.013 (3)
C4B0.072 (4)0.074 (5)0.042 (3)0.014 (4)0.020 (3)0.002 (3)
C5B0.069 (4)0.059 (4)0.047 (3)0.014 (4)0.027 (3)0.015 (3)
C6B0.053 (3)0.041 (4)0.050 (3)0.011 (3)0.024 (3)0.005 (3)
C7B0.052 (3)0.037 (3)0.041 (3)0.006 (3)0.021 (2)0.002 (2)
C8B0.057 (3)0.048 (4)0.064 (3)0.000 (3)0.026 (3)0.002 (3)
N9B0.047 (3)0.048 (3)0.059 (3)0.005 (3)0.026 (2)0.008 (3)
C10B0.060 (4)0.061 (4)0.069 (4)0.004 (3)0.027 (3)0.018 (3)
C11B0.059 (3)0.048 (3)0.043 (3)0.006 (3)0.025 (3)0.006 (3)
C12B0.053 (3)0.040 (3)0.046 (3)0.001 (3)0.026 (3)0.000 (3)
C13B0.073 (4)0.034 (3)0.062 (3)0.007 (3)0.037 (3)0.001 (3)
N14B0.063 (3)0.046 (3)0.056 (3)0.000 (3)0.030 (2)0.009 (3)
O15B0.081 (3)0.051 (3)0.065 (3)0.010 (2)0.046 (2)0.011 (2)
Geometric parameters (Å, º) top
C3A—C8A1.372 (6)C3B—C8B1.377 (6)
C3A—C4A1.398 (7)C3B—C4B1.393 (8)
C4A—C5A1.361 (7)C4B—C5B1.367 (8)
C5A—C6A1.388 (6)C5B—C6B1.397 (7)
C6A—N9A1.380 (6)C6B—N9B1.369 (6)
C6A—C7A1.390 (6)C6B—C7B1.404 (7)
C7A—C8A1.395 (7)C7B—C8B1.393 (7)
C7A—C12A1.438 (6)C7B—C12B1.439 (6)
N9A—C11A1.355 (6)N9B—C11B1.349 (5)
N9A—C10A1.459 (6)N9B—C10B1.449 (6)
C11A—C12A1.357 (7)C11B—C12B1.380 (7)
C12A—C13A1.437 (7)C12B—C13B1.427 (6)
C13A—N14A1.292 (6)C13B—N14B1.288 (6)
N14A—O15A1.392 (6)N14B—O15B1.402 (6)
C8A—C3A—C4A120.3 (5)C8B—C3B—C4B121.0 (6)
C5A—C4A—C3A122.4 (5)C5B—C4B—C3B121.2 (5)
C4A—C5A—C6A116.6 (5)C4B—C5B—C6B117.9 (5)
N9A—C6A—C5A129.5 (5)N9B—C6B—C5B131.0 (5)
N9A—C6A—C7A107.6 (4)N9B—C6B—C7B107.3 (4)
C5A—C6A—C7A122.9 (5)C5B—C6B—C7B121.7 (5)
C6A—C7A—C8A118.9 (4)C8B—C7B—C6B118.9 (4)
C6A—C7A—C12A107.2 (4)C8B—C7B—C12B134.2 (5)
C8A—C7A—C12A133.9 (5)C6B—C7B—C12B106.9 (5)
C3A—C8A—C7A118.9 (5)C3B—C8B—C7B119.3 (5)
C11A—N9A—C6A108.5 (4)C11B—N9B—C6B110.2 (4)
C11A—N9A—C10A126.2 (5)C11B—N9B—C10B125.1 (5)
C6A—N9A—C10A125.2 (4)C6B—N9B—C10B124.7 (4)
N9A—C11A—C12A110.8 (5)N9B—C11B—C12B109.6 (5)
C11A—C12A—C7A105.9 (4)C11B—C12B—C13B129.3 (5)
C11A—C12A—C13A129.7 (5)C11B—C12B—C7B106.1 (4)
C7A—C12A—C13A124.4 (5)C13B—C12B—C7B124.6 (5)
N14A—C13A—C12A130.4 (5)N14B—C13B—C12B132.2 (5)
C13A—N14A—O15A110.1 (5)C13B—N14B—O15B111.2 (4)
C8A—C3A—C4A—C5A1.0 (9)C8B—C3B—C4B—C5B0.6 (9)
C3A—C4A—C5A—C6A1.1 (8)C3B—C4B—C5B—C6B0.2 (8)
C4A—C5A—C6A—N9A179.6 (5)C4B—C5B—C6B—N9B179.9 (5)
C4A—C5A—C6A—C7A0.5 (7)C4B—C5B—C6B—C7B0.4 (7)
N9A—C6A—C7A—C8A179.2 (4)N9B—C6B—C7B—C8B179.5 (4)
C5A—C6A—C7A—C8A0.0 (7)C5B—C6B—C7B—C8B0.2 (7)
N9A—C6A—C7A—C12A1.2 (5)N9B—C6B—C7B—C12B1.3 (5)
C5A—C6A—C7A—C12A179.6 (5)C5B—C6B—C7B—C12B178.4 (5)
C4A—C3A—C8A—C7A0.4 (8)C4B—C3B—C8B—C7B1.3 (8)
C6A—C7A—C8A—C3A0.1 (7)C6B—C7B—C8B—C3B1.1 (7)
C12A—C7A—C8A—C3A179.3 (5)C12B—C7B—C8B—C3B178.7 (5)
C5A—C6A—N9A—C11A179.6 (5)C5B—C6B—N9B—C11B178.5 (5)
C7A—C6A—N9A—C11A1.3 (5)C7B—C6B—N9B—C11B1.2 (6)
C5A—C6A—N9A—C10A0.8 (8)C5B—C6B—N9B—C10B2.5 (8)
C7A—C6A—N9A—C10A179.9 (4)C7B—C6B—N9B—C10B177.8 (4)
C6A—N9A—C11A—C12A0.8 (6)C6B—N9B—C11B—C12B0.6 (6)
C10A—N9A—C11A—C12A179.6 (5)C10B—N9B—C11B—C12B178.4 (5)
N9A—C11A—C12A—C7A0.1 (6)N9B—C11B—C12B—C13B177.1 (5)
N9A—C11A—C12A—C13A177.8 (5)N9B—C11B—C12B—C7B0.3 (6)
C6A—C7A—C12A—C11A0.7 (6)C8B—C7B—C12B—C11B178.8 (6)
C8A—C7A—C12A—C11A179.8 (5)C6B—C7B—C12B—C11B1.0 (5)
C6A—C7A—C12A—C13A178.8 (5)C8B—C7B—C12B—C13B4.3 (9)
C8A—C7A—C12A—C13A1.8 (9)C6B—C7B—C12B—C13B178.0 (5)
C11A—C12A—C13A—N14A17.2 (9)C11B—C12B—C13B—N14B18.7 (1)
C7A—C12A—C13A—N14A165.3 (5)C7B—C12B—C13B—N14B165.1 (5)
C12A—C13A—N14A—O15A0.4 (8)C12B—C13B—N14B—O15B2.9 (8)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O15A—H15A···N14Bi0.821.892.709 (5)176
O15B—H15B···N14Ai0.822.112.895 (6)162
Symmetry code: (i) x+1, y+1/2, z.
(II) (E)-5-Methoxy-1-Methylindole-3-carboxyaldehyde oxime top
Crystal data top
C11H12N2O2Z = 8
Mr = 204.23F(000) = 864
Triclinic, P1Dx = 1.277 Mg m3
a = 8.2351 (2) ÅCu Kα radiation, λ = 1.54180 Å
b = 15.8892 (7) ÅCell parameters from 21 reflections
c = 17.8070 (11) Åθ = 20.8–42.1°
α = 71.148 (4)°µ = 0.73 mm1
β = 81.245 (4)°T = 293 K
γ = 75.124 (3)°Needle, colourless
V = 2125.02 (17) Å30.60 × 0.20 × 0.03 mm
Data collection top
Enraf-Nonius CAD-4
diffractometer
4302 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.025
Graphite monochromatorθmax = 66.1°, θmin = 2.6°
ω–2θ scansh = 95
Absorption correction: ψ scan
(North et al., 1968)
k = 1817
Tmin = 0.755, Tmax = 0.854l = 2120
10056 measured reflections3 standard reflections every 200 reflections
7107 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)] = 0.054H-atom parameters constrained
wR(F2) = 0.173Calculated w = 1/[σ2(Fo2) + (0.1003P)2 + 0.0623P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.005
7107 reflectionsΔρmax = 0.20 e Å3
554 parametersΔρmin = 0.18 e Å3
216 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0058 (5)
Crystal data top
C11H12N2O2γ = 75.124 (3)°
Mr = 204.23V = 2125.02 (17) Å3
Triclinic, P1Z = 8
a = 8.2351 (2) ÅCu Kα radiation
b = 15.8892 (7) ŵ = 0.73 mm1
c = 17.8070 (11) ÅT = 293 K
α = 71.148 (4)°0.60 × 0.20 × 0.03 mm
β = 81.245 (4)°
Data collection top
Enraf-Nonius CAD-4
diffractometer
4302 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)
Rint = 0.025
Tmin = 0.755, Tmax = 0.8543 standard reflections every 200 reflections
10056 measured reflections intensity decay: none
7107 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.054216 restraints
wR(F2) = 0.173H-atom parameters constrained
S = 1.05Δρmax = 0.20 e Å3
7107 reflectionsΔρmin = 0.18 e Å3
554 parameters
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
C1A0.2798 (6)0.1015 (3)0.4897 (3)0.162 (2)
H1A10.38360.05630.49340.194*
H1A20.21090.08700.53860.194*
H1A30.30340.16030.48000.194*
O2A0.1958 (4)0.1026 (2)0.4281 (2)0.1520 (13)
C3A0.0366 (4)0.1559 (2)0.4164 (2)0.1007 (11)
C4A0.0627 (5)0.1364 (3)0.3692 (2)0.1222 (15)
H4A0.01950.08740.34880.147*
C5A0.2192 (4)0.1869 (2)0.3529 (2)0.1072 (13)
H5A0.28320.17410.32090.129*
C6A0.2818 (3)0.25848 (19)0.38517 (16)0.0795 (9)
C7A0.1856 (3)0.27979 (16)0.43241 (14)0.0659 (7)
C8A0.0234 (3)0.22759 (18)0.44775 (16)0.0748 (8)
H8A0.04260.24090.47850.090*
N9A0.4375 (3)0.31834 (18)0.37950 (15)0.0884 (8)
C10A0.5717 (4)0.3209 (3)0.3337 (2)0.1269 (16)
H10A0.59700.26160.34910.152*
H10B0.53620.33820.27800.152*
H10C0.67060.36440.34390.152*
C11A0.4403 (3)0.37657 (19)0.42097 (17)0.0811 (9)
H11A0.53140.42370.42590.097*
C12A0.2913 (3)0.35703 (16)0.45472 (14)0.0656 (7)
C13A0.2581 (3)0.40740 (18)0.50208 (15)0.0692 (7)
H13A0.34470.45370.51280.083*
N14A0.1175 (3)0.39278 (15)0.53043 (13)0.0673 (6)
O15A0.1247 (3)0.45155 (15)0.57653 (14)0.0897 (7)
H15A0.03180.44260.59270.108*
C1B0.1246 (4)0.6800 (2)0.7871 (2)0.0933 (10)
H1B10.23650.71190.77250.112*
H1B20.04850.72000.76450.112*
H1B30.12320.66000.84400.112*
O2B0.0736 (2)0.60327 (14)0.75792 (13)0.0870 (7)
C3B0.0913 (3)0.55582 (18)0.76276 (16)0.0682 (7)
C4B0.1995 (3)0.5649 (2)0.81181 (16)0.0779 (8)
H4B0.16020.60510.84200.093*
C5B0.3620 (3)0.5155 (2)0.81580 (16)0.0776 (8)
H5B0.43350.52130.84870.093*
C6B0.4180 (3)0.45656 (17)0.76965 (15)0.0654 (7)
C7B0.3107 (3)0.44605 (16)0.72031 (13)0.0580 (6)
C8B0.1459 (3)0.49641 (16)0.71765 (14)0.0626 (7)
H8B0.07280.49020.68580.075*
N9B0.5759 (2)0.40192 (16)0.76053 (13)0.0745 (7)
C10B0.7229 (4)0.3936 (3)0.8009 (2)0.1017 (11)
H10D0.70680.36110.85620.122*
H10E0.73780.45320.79570.122*
H10F0.82110.36080.77740.122*
C11B0.5697 (3)0.35883 (18)0.70716 (15)0.0693 (7)
H11B0.66070.31840.69080.083*
C12B0.4124 (3)0.38231 (17)0.68027 (14)0.0611 (7)
C13B0.3709 (3)0.34638 (18)0.62310 (14)0.0634 (7)
H13B0.45590.30580.60360.076*
N14B0.2261 (3)0.36631 (15)0.59734 (12)0.0648 (6)
O15B0.2258 (3)0.31724 (14)0.54326 (12)0.0797 (6)
H15B0.13240.33150.52630.096*
C1C0.6215 (5)0.1051 (3)0.60024 (19)0.1031 (12)
H1C10.53130.08370.58940.124*
H1C20.72750.06790.58780.124*
H1C30.61550.16730.56820.124*
O2C0.6066 (3)0.10007 (16)0.68205 (11)0.0933 (7)
C3C0.7317 (3)0.11950 (18)0.71208 (14)0.0665 (7)
C4C0.8627 (3)0.1562 (2)0.66456 (14)0.0758 (8)
H4C0.86960.16660.60980.091*
C5C0.9813 (3)0.1772 (2)0.69749 (13)0.0749 (8)
H5C1.06830.20200.66570.090*
C6C0.9686 (3)0.16068 (17)0.77920 (12)0.0612 (7)
C7C0.8380 (3)0.12268 (16)0.82832 (11)0.0540 (6)
C8C0.7185 (3)0.10269 (16)0.79368 (12)0.0589 (7)
H8C0.63060.07830.82490.071*
N9C1.0707 (3)0.17415 (16)0.82718 (12)0.0705 (6)
C10C1.2178 (4)0.2135 (2)0.80034 (19)0.0967 (11)
H10G1.18380.27620.76950.116*
H10H1.29480.18040.76810.116*
H10I1.27220.21000.84560.116*
C11C1.0085 (3)0.14496 (18)0.90371 (13)0.0686 (7)
H11C1.05560.14700.94720.082*
C12C0.8684 (3)0.11230 (17)0.90879 (12)0.0571 (6)
C13C0.7832 (3)0.07139 (18)0.98329 (13)0.0615 (7)
H13C0.82110.07081.03010.074*
N14C0.6586 (3)0.03604 (14)0.98809 (11)0.0616 (6)
O15C0.6038 (3)0.00210 (16)1.06859 (10)0.0845 (6)
H15C0.51820.02031.07040.101*
C1D0.6362 (7)0.0596 (3)1.2327 (2)0.148 (2)
H1D10.52330.05621.25450.177*
H1D20.70960.03951.27510.177*
H1D30.67310.02121.19860.177*
O2D0.6403 (3)0.15132 (15)1.18796 (14)0.1108 (8)
C3D0.7878 (4)0.17145 (18)1.14763 (17)0.0846 (10)
C4D0.9437 (4)0.11039 (19)1.15949 (19)0.0998 (12)
H4D0.94980.05251.19560.120*
C5D1.0876 (4)0.13441 (18)1.11874 (19)0.1014 (12)
H5D1.19140.09351.12670.122*
C6D1.0755 (3)0.22120 (16)1.06515 (16)0.0803 (9)
C7D0.9186 (3)0.28396 (15)1.05226 (14)0.0663 (7)
C8D0.7749 (3)0.25784 (16)1.09412 (15)0.0738 (8)
H8D0.67040.29801.08640.089*
N9D1.1984 (3)0.26227 (17)1.01692 (16)0.0907 (8)
C10D1.3792 (3)0.2233 (3)1.0141 (3)0.1327 (16)
H10J1.40020.16521.00460.159*
H10K1.42110.21551.06390.159*
H10L1.43530.26350.97200.159*
C11D1.1243 (3)0.34815 (18)0.97538 (18)0.0848 (9)
H11D1.18150.38950.93900.102*
C12D0.9544 (3)0.36572 (15)0.99418 (15)0.0663 (7)
C13D0.8455 (3)0.45320 (15)0.96149 (16)0.0677 (7)
H13D0.89220.49830.92380.081*
N14D0.6890 (3)0.47187 (13)0.98148 (13)0.0652 (6)
O15D0.6150 (2)0.56374 (12)0.94160 (14)0.0876 (7)
H15D0.51350.57400.95410.105*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C1A0.153 (4)0.163 (4)0.176 (5)0.061 (3)0.089 (4)0.100 (4)
O2A0.146 (3)0.156 (3)0.175 (3)0.051 (2)0.068 (2)0.116 (2)
C3A0.115 (3)0.103 (3)0.095 (2)0.003 (2)0.030 (2)0.056 (2)
C4A0.160 (4)0.124 (3)0.112 (3)0.015 (3)0.038 (3)0.075 (3)
C5A0.136 (4)0.122 (3)0.086 (2)0.034 (3)0.035 (2)0.044 (2)
C6A0.101 (3)0.090 (2)0.0569 (17)0.034 (2)0.0160 (16)0.0205 (16)
C7A0.0773 (19)0.0741 (18)0.0490 (14)0.0248 (16)0.0089 (13)0.0138 (13)
C8A0.085 (2)0.084 (2)0.0616 (17)0.0123 (17)0.0172 (15)0.0306 (15)
N9A0.0838 (19)0.112 (2)0.0733 (17)0.0350 (17)0.0227 (14)0.0151 (16)
C10A0.122 (3)0.164 (4)0.111 (3)0.061 (3)0.051 (3)0.020 (3)
C11A0.075 (2)0.089 (2)0.078 (2)0.0230 (17)0.0117 (17)0.0153 (17)
C12A0.0664 (18)0.0728 (18)0.0581 (16)0.0252 (15)0.0060 (13)0.0117 (14)
C13A0.0619 (18)0.0686 (18)0.0768 (19)0.0174 (14)0.0005 (15)0.0213 (15)
N14A0.0714 (16)0.0714 (15)0.0676 (14)0.0210 (12)0.0004 (12)0.0305 (12)
O15A0.0870 (15)0.0991 (16)0.1066 (17)0.0250 (13)0.0000 (13)0.0621 (14)
C1B0.102 (3)0.089 (2)0.099 (2)0.0067 (19)0.022 (2)0.047 (2)
O2B0.0775 (15)0.1044 (16)0.1004 (16)0.0109 (12)0.0099 (12)0.0652 (14)
C3B0.0664 (18)0.0823 (19)0.0648 (17)0.0218 (16)0.0039 (14)0.0301 (15)
C4B0.087 (2)0.091 (2)0.0729 (19)0.0235 (18)0.0081 (16)0.0437 (17)
C5B0.084 (2)0.095 (2)0.0716 (19)0.0255 (18)0.0151 (16)0.0392 (17)
C6B0.0690 (18)0.0751 (18)0.0610 (16)0.0266 (15)0.0073 (14)0.0228 (14)
C7B0.0617 (16)0.0684 (17)0.0497 (14)0.0272 (14)0.0004 (12)0.0174 (12)
C8B0.0703 (18)0.0763 (18)0.0534 (15)0.0293 (15)0.0026 (13)0.0264 (14)
N9B0.0674 (16)0.0885 (17)0.0774 (16)0.0206 (13)0.0155 (13)0.0309 (14)
C10B0.082 (2)0.120 (3)0.119 (3)0.016 (2)0.034 (2)0.050 (2)
C11B0.0678 (18)0.0724 (18)0.0747 (18)0.0206 (15)0.0045 (15)0.0277 (15)
C12B0.0643 (17)0.0675 (17)0.0584 (15)0.0245 (14)0.0007 (13)0.0224 (13)
C13B0.0635 (17)0.0691 (17)0.0636 (16)0.0215 (14)0.0027 (14)0.0258 (14)
N14B0.0742 (16)0.0705 (14)0.0610 (13)0.0228 (12)0.0010 (11)0.0312 (11)
O15B0.0816 (14)0.0936 (15)0.0828 (14)0.0185 (12)0.0094 (11)0.0511 (12)
C1C0.143 (3)0.107 (3)0.078 (2)0.031 (2)0.032 (2)0.040 (2)
O2C0.1182 (18)0.1147 (17)0.0627 (13)0.0555 (15)0.0198 (12)0.0188 (12)
C3C0.0797 (19)0.0667 (17)0.0574 (16)0.0239 (15)0.0094 (14)0.0164 (13)
C4C0.092 (2)0.083 (2)0.0522 (16)0.0271 (18)0.0015 (16)0.0159 (15)
C5C0.078 (2)0.080 (2)0.0586 (17)0.0279 (16)0.0055 (15)0.0070 (15)
C6C0.0622 (16)0.0615 (16)0.0590 (16)0.0195 (13)0.0041 (13)0.0125 (13)
C7C0.0565 (15)0.0515 (14)0.0519 (14)0.0134 (12)0.0042 (12)0.0113 (11)
C8C0.0652 (17)0.0588 (15)0.0511 (14)0.0179 (13)0.0046 (12)0.0108 (12)
N9C0.0642 (15)0.0771 (15)0.0696 (15)0.0301 (12)0.0058 (12)0.0093 (12)
C10C0.084 (2)0.112 (3)0.097 (2)0.056 (2)0.0069 (19)0.008 (2)
C11C0.0711 (18)0.0730 (18)0.0633 (17)0.0202 (15)0.0119 (14)0.0161 (14)
C12C0.0544 (15)0.0619 (16)0.0558 (15)0.0161 (13)0.0060 (12)0.0155 (12)
C13C0.0619 (17)0.0726 (18)0.0507 (14)0.0168 (14)0.0046 (12)0.0176 (13)
N14C0.0629 (14)0.0699 (14)0.0455 (12)0.0160 (11)0.0031 (10)0.0106 (10)
O15C0.0875 (16)0.1137 (17)0.0486 (11)0.0409 (13)0.0063 (10)0.0102 (10)
C1D0.279 (6)0.099 (3)0.088 (3)0.099 (4)0.034 (3)0.007 (2)
O2D0.161 (3)0.0855 (16)0.0940 (17)0.0560 (17)0.0207 (17)0.0101 (13)
C3D0.123 (3)0.067 (2)0.073 (2)0.021 (2)0.029 (2)0.0221 (17)
C4D0.153 (4)0.062 (2)0.089 (3)0.012 (2)0.043 (3)0.0226 (18)
C5D0.129 (3)0.066 (2)0.109 (3)0.024 (2)0.058 (3)0.039 (2)
C6D0.085 (2)0.076 (2)0.090 (2)0.0018 (18)0.0270 (19)0.0450 (18)
C7D0.0713 (19)0.0637 (17)0.0727 (18)0.0025 (15)0.0246 (15)0.0334 (15)
C8D0.094 (2)0.0617 (18)0.0725 (18)0.0109 (16)0.0268 (17)0.0247 (15)
N9D0.0693 (18)0.091 (2)0.117 (2)0.0140 (16)0.0275 (17)0.0541 (18)
C10D0.072 (2)0.130 (3)0.199 (5)0.027 (2)0.037 (3)0.078 (3)
C11D0.071 (2)0.088 (2)0.102 (2)0.0055 (18)0.0142 (18)0.044 (2)
C12D0.0589 (17)0.0685 (18)0.0768 (18)0.0046 (14)0.0140 (14)0.0322 (15)
C13D0.0606 (18)0.0678 (18)0.0750 (18)0.0130 (14)0.0086 (14)0.0211 (15)
N14D0.0601 (14)0.0574 (13)0.0749 (15)0.0033 (11)0.0153 (12)0.0184 (11)
O15D0.0690 (13)0.0657 (13)0.1087 (17)0.0018 (10)0.0151 (13)0.0063 (12)
Geometric parameters (Å, º) top
C1A—O2A1.375 (4)C1C—O2C1.421 (3)
O2A—C3A1.371 (3)O2C—C3C1.371 (2)
C3A—C8A1.375 (3)C3C—C8C1.382 (3)
C3A—C4A1.407 (3)C3C—C4C1.395 (3)
C4A—C5A1.350 (3)C4C—C5C1.371 (3)
C5A—C6A1.386 (3)C5C—C6C1.385 (3)
C6A—N9A1.382 (3)C6C—N9C1.383 (2)
C6A—C7A1.405 (3)C6C—C7C1.411 (3)
C7A—C8A1.394 (3)C7C—C8C1.386 (2)
C7A—C12A1.443 (3)C7C—C12C1.442 (2)
N9A—C11A1.352 (3)N9C—C11C1.355 (3)
N9A—C10A1.455 (3)N9C—C10C1.452 (3)
C11A—C12A1.368 (3)C11C—C12C1.362 (3)
C12A—C13A1.430 (3)C12C—C13C1.438 (2)
C13A—N14A1.270 (3)C13C—N14C1.271 (2)
N14A—O15A1.415 (2)N14C—O15C1.417 (2)
C1B—O2B1.418 (3)C1D—O2D1.423 (4)
O2B—C3B1.373 (3)O2D—C3D1.371 (3)
C3B—C8B1.379 (3)C3D—C8D1.384 (3)
C3B—C4B1.401 (3)C3D—C4D1.394 (3)
C4B—C5B1.366 (3)C4D—C5D1.367 (3)
C5B—C6B1.388 (3)C5D—C6D1.389 (3)
C6B—N9B1.385 (3)C6D—N9D1.379 (3)
C6B—C7B1.409 (3)C6D—C7D1.414 (3)
C7B—C8B1.387 (3)C7D—C8D1.383 (3)
C7B—C12B1.444 (3)C7D—C12D1.442 (3)
N9B—C11B1.352 (3)N9D—C11D1.356 (3)
N9B—C10B1.456 (3)N9D—C10D1.458 (3)
C11B—C12B1.368 (3)C11D—C12D1.366 (3)
C12B—C13B1.436 (2)C12D—C13D1.439 (3)
C13B—N14B1.270 (3)C13D—N14D1.268 (3)
N14B—O15B1.422 (2)N14D—O15D1.418 (2)
C3A—O2A—C1A119.7 (3)C3C—O2C—C1C119.1 (2)
O2A—C3A—C8A121.6 (2)O2C—C3C—C8C115.7 (2)
O2A—C3A—C4A117.6 (2)O2C—C3C—C4C123.3 (2)
C8A—C3A—C4A120.8 (2)C8C—C3C—C4C121.0 (2)
C5A—C4A—C3A121.6 (3)C5C—C4C—C3C120.9 (2)
C4A—C5A—C6A118.0 (2)C4C—C5C—C6C118.4 (2)
N9A—C6A—C5A129.5 (2)N9C—C6C—C5C130.2 (2)
N9A—C6A—C7A108.8 (2)N9C—C6C—C7C108.2 (2)
C5A—C6A—C7A121.7 (2)C5C—C6C—C7C121.6 (2)
C8A—C7A—C6A119.4 (2)C8C—C7C—C6C119.1 (2)
C8A—C7A—C12A134.9 (2)C8C—C7C—C12C134.8 (2)
C6A—C7A—C12A105.7 (2)C6C—C7C—C12C106.1 (2)
C3A—C8A—C7A118.4 (2)C3C—C8C—C7C119.1 (2)
C11A—N9A—C6A108.0 (2)C11C—N9C—C6C108.1 (2)
C11A—N9A—C10A126.1 (3)C11C—N9C—C10C125.9 (2)
C6A—N9A—C10A125.9 (2)C6C—N9C—C10C126.1 (2)
N9A—C11A—C12A111.0 (2)N9C—C11C—C12C111.3 (2)
C11A—C12A—C13A123.4 (2)C11C—C12C—C13C123.1 (2)
C11A—C12A—C7A106.5 (2)C11C—C12C—C7C106.3 (2)
C13A—C12A—C7A130.1 (2)C13C—C12C—C7C130.5 (2)
N14A—C13A—C12A124.0 (2)N14C—C13C—C12C123.0 (2)
C13A—N14A—O15A110.9 (2)C13C—N14C—O15C111.0 (2)
C3B—O2B—C1B118.5 (2)C3D—O2D—C1D119.6 (3)
O2B—C3B—C8B116.5 (2)O2D—C3D—C8D116.0 (2)
O2B—C3B—C4B122.6 (2)O2D—C3D—C4D123.2 (2)
C8B—C3B—C4B120.8 (2)C8D—C3D—C4D120.8 (2)
C5B—C4B—C3B120.9 (2)C5D—C4D—C3D120.9 (2)
C4B—C5B—C6B118.4 (2)C4D—C5D—C6D118.6 (2)
N9B—C6B—C5B130.0 (2)N9D—C6D—C5D130.5 (2)
N9B—C6B—C7B108.4 (2)N9D—C6D—C7D108.2 (2)
C5B—C6B—C7B121.6 (2)C5D—C6D—C7D121.3 (2)
C8B—C7B—C6B119.0 (2)C8D—C7D—C6D118.9 (2)
C8B—C7B—C12B135.0 (2)C8D—C7D—C12D135.1 (2)
C6B—C7B—C12B106.0 (2)C6D—C7D—C12D105.9 (2)
C3B—C8B—C7B119.3 (2)C7D—C8D—C3D119.5 (2)
C11B—N9B—C6B108.1 (2)C11D—N9D—C6D108.4 (2)
C11B—N9B—C10B126.2 (2)C11D—N9D—C10D125.0 (3)
C6B—N9B—C10B125.7 (2)C6D—N9D—C10D126.4 (2)
N9B—C11B—C12B111.3 (2)N9D—C11D—C12D110.9 (2)
C11B—C12B—C13B122.9 (2)C11D—C12D—C13D122.7 (2)
C11B—C12B—C7B106.3 (2)C11D—C12D—C7D106.5 (2)
C13B—C12B—C7B130.8 (2)C13D—C12D—C7D130.8 (2)
N14B—C13B—C12B124.4 (2)N14D—C13D—C12D123.3 (2)
C13B—N14B—O15B110.3 (2)C13D—N14D—O15D110.9 (2)
C1A—O2A—C3A—C8A19.4 (7)C1C—O2C—C3C—C8C172.6 (3)
C1A—O2A—C3A—C4A162.1 (5)C1C—O2C—C3C—C4C9.1 (4)
O2A—C3A—C4A—C5A178.2 (4)O2C—C3C—C4C—C5C177.8 (3)
C8A—C3A—C4A—C5A0.2 (7)C8C—C3C—C4C—C5C0.4 (5)
C3A—C4A—C5A—C6A1.1 (7)C3C—C4C—C5C—C6C0.3 (5)
C4A—C5A—C6A—N9A178.1 (4)C4C—C5C—C6C—N9C179.1 (3)
C4A—C5A—C6A—C7A1.2 (6)C4C—C5C—C6C—C7C0.4 (4)
N9A—C6A—C7A—C8A179.1 (3)N9C—C6C—C7C—C8C179.9 (2)
C5A—C6A—C7A—C8A0.3 (4)C5C—C6C—C7C—C8C0.9 (4)
N9A—C6A—C7A—C12A0.6 (3)N9C—C6C—C7C—C12C1.0 (3)
C5A—C6A—C7A—C12A180.0 (3)C5C—C6C—C7C—C12C177.9 (3)
O2A—C3A—C8A—C7A179.0 (3)O2C—C3C—C8C—C7C178.5 (2)
C4A—C3A—C8A—C7A0.6 (5)C4C—C3C—C8C—C7C0.1 (4)
C6A—C7A—C8A—C3A0.6 (4)C6C—C7C—C8C—C3C0.8 (4)
C12A—C7A—C8A—C3A179.0 (3)C12C—C7C—C8C—C3C177.7 (3)
C5A—C6A—N9A—C11A180.0 (3)C5C—C6C—N9C—C11C178.2 (3)
C7A—C6A—N9A—C11A0.6 (3)C7C—C6C—N9C—C11C0.6 (3)
C5A—C6A—N9A—C10A2.7 (6)C5C—C6C—N9C—C10C2.3 (5)
C7A—C6A—N9A—C10A177.9 (3)C7C—C6C—N9C—C10C178.8 (3)
C6A—N9A—C11A—C12A0.4 (4)C6C—N9C—C11C—C12C0.1 (3)
C10A—N9A—C11A—C12A177.7 (3)C10C—N9C—C11C—C12C179.5 (3)
N9A—C11A—C12A—C13A180.0 (3)N9C—C11C—C12C—C13C175.8 (2)
N9A—C11A—C12A—C7A0.1 (3)N9C—C11C—C12C—C7C0.7 (3)
C8A—C7A—C12A—C11A179.3 (3)C8C—C7C—C12C—C11C179.6 (3)
C6A—C7A—C12A—C11A0.3 (3)C6C—C7C—C12C—C11C1.1 (3)
C8A—C7A—C12A—C13A0.8 (5)C8C—C7C—C12C—C13C3.5 (5)
C6A—C7A—C12A—C13A179.6 (3)C6C—C7C—C12C—C13C175.0 (3)
C11A—C12A—C13A—N14A176.4 (3)C11C—C12C—C13C—N14C175.7 (3)
C7A—C12A—C13A—N14A3.6 (5)C7C—C12C—C13C—N14C0.1 (4)
C12A—C13A—N14A—O15A178.3 (2)C12C—C13C—N14C—O15C177.8 (2)
C1B—O2B—C3B—C8B165.0 (3)C1D—O2D—C3D—C8D168.4 (3)
C1B—O2B—C3B—C4B16.2 (4)C1D—O2D—C3D—C4D12.6 (5)
O2B—C3B—C4B—C5B179.1 (3)O2D—C3D—C4D—C5D178.8 (3)
C8B—C3B—C4B—C5B0.4 (5)C8D—C3D—C4D—C5D0.2 (5)
C3B—C4B—C5B—C6B0.5 (5)C3D—C4D—C5D—C6D0.1 (5)
C4B—C5B—C6B—N9B177.4 (3)C4D—C5D—C6D—N9D179.8 (3)
C4B—C5B—C6B—C7B0.9 (4)C4D—C5D—C6D—C7D0.2 (5)
N9B—C6B—C7B—C8B178.2 (2)N9D—C6D—C7D—C8D179.7 (2)
C5B—C6B—C7B—C8B0.4 (4)C5D—C6D—C7D—C8D0.0 (4)
N9B—C6B—C7B—C12B0.3 (3)N9D—C6D—C7D—C12D0.7 (3)
C5B—C6B—C7B—C12B178.3 (3)C5D—C6D—C7D—C12D179.6 (3)
O2B—C3B—C8B—C7B179.6 (2)C6D—C7D—C8D—C3D0.2 (4)
C4B—C3B—C8B—C7B0.8 (4)C12D—C7D—C8D—C3D179.2 (3)
C6B—C7B—C8B—C3B0.4 (4)O2D—C3D—C8D—C7D178.7 (2)
C12B—C7B—C8B—C3B176.7 (3)C4D—C3D—C8D—C7D0.3 (4)
C5B—C6B—N9B—C11B178.1 (3)C5D—C6D—N9D—C11D179.7 (3)
C7B—C6B—N9B—C11B0.4 (3)C7D—C6D—N9D—C11D0.7 (3)
C5B—C6B—N9B—C10B1.2 (5)C5D—C6D—N9D—C10D3.4 (6)
C7B—C6B—N9B—C10B179.7 (3)C7D—C6D—N9D—C10D176.9 (3)
C6B—N9B—C11B—C12B0.3 (3)C6D—N9D—C11D—C12D0.3 (4)
C10B—N9B—C11B—C12B179.6 (3)C10D—N9D—C11D—C12D176.6 (3)
N9B—C11B—C12B—C13B180.0 (2)N9D—C11D—C12D—C13D177.1 (3)
N9B—C11B—C12B—C7B0.1 (3)N9D—C11D—C12D—C7D0.1 (3)
C8B—C7B—C12B—C11B177.5 (3)C8D—C7D—C12D—C11D180.0 (3)
C6B—C7B—C12B—C11B0.1 (3)C6D—C7D—C12D—C11D0.5 (3)
C8B—C7B—C12B—C13B2.3 (5)C8D—C7D—C12D—C13D3.0 (5)
C6B—C7B—C12B—C13B179.8 (3)C6D—C7D—C12D—C13D176.4 (3)
C11B—C12B—C13B—N14B179.5 (3)C11D—C12D—C13D—N14D176.3 (3)
C7B—C12B—C13B—N14B0.6 (5)C7D—C12D—C13D—N14D0.3 (5)
C12B—C13B—N14B—O15B178.3 (2)C12D—C13D—N14D—O15D178.1 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O15A—H15A···N14B0.822.162.882 (3)147
O15B—H15B···N14A0.822.042.786 (3)151
O15C—H15C···N14Ci0.822.022.755 (3)149
O15D—H15D···N14Dii0.822.032.765 (3)149
Symmetry codes: (i) x+1, y, z+2; (ii) x+1, y+1, z+2.

Experimental details

(I)(II)
Crystal data
Chemical formulaC10H10N2OC11H12N2O2
Mr174.20204.23
Crystal system, space groupMonoclinic, P21Triclinic, P1
Temperature (K)293293
a, b, c (Å)13.462 (4), 5.079 (4), 14.127 (4)8.2351 (2), 15.8892 (7), 17.8070 (11)
α, β, γ (°)90.00 (4), 111.53 (4), 90.00 (4)71.148 (4), 81.245 (4), 75.124 (3)
V3)898.4 (8)2125.02 (17)
Z48
Radiation typeCu KαCu Kα
µ (mm1)0.690.73
Crystal size (mm)0.30 × 0.20 × 0.150.60 × 0.20 × 0.03
Data collection
DiffractometerEnraf-Nonius CAD-4
diffractometer
Enraf-Nonius CAD-4
diffractometer
Absorption correctionψ scan
(North et al., 1968)
Tmin, Tmax0.755, 0.854
No. of measured, independent and
observed [I > 2σ(I)] reflections
3706, 2045, 1039 10056, 7107, 4302
Rint0.0520.025
(sin θ/λ)max1)0.6240.593
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.129, 1.00 0.054, 0.173, 1.05
No. of reflections20457107
No. of parameters240554
No. of restraints1216
H-atom treatmentH-atom parameters constrainedH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.17, 0.200.20, 0.18

Computer programs: CAD-4 Software (Enraf-Nonius, 1989), CAD-4 Software, CAD77 and CADRAL (Korber, 1982), and CADSHEL (Cooper, 1990), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997).

Selected geometric parameters (Å, º) for (I) top
C3A—C8A1.372 (6)N9A—C11A1.355 (6)
C3A—C4A1.398 (7)N9A—C10A1.459 (6)
C4A—C5A1.361 (7)C11A—C12A1.357 (7)
C5A—C6A1.388 (6)C12A—C13A1.437 (7)
C6A—N9A1.380 (6)C13A—N14A1.292 (6)
C6A—C7A1.390 (6)N14A—O15A1.392 (6)
C7A—C8A1.395 (7)C13B—N14B1.288 (6)
C7A—C12A1.438 (6)N14B—O15B1.402 (6)
C11A—C12A—C7A105.9 (4)C11B—C12B—C13B129.3 (5)
C11A—C12A—C13A129.7 (5)C11B—C12B—C7B106.1 (4)
C7A—C12A—C13A124.4 (5)C13B—C12B—C7B124.6 (5)
N14A—C13A—C12A130.4 (5)N14B—C13B—C12B132.2 (5)
C13A—N14A—O15A110.1 (5)C13B—N14B—O15B111.2 (4)
Hydrogen-bond geometry (Å, º) for (I) top
D—H···AD—HH···AD···AD—H···A
O15A—H15A···N14Bi0.821.892.709 (5)175.5
O15B—H15B···N14Ai0.822.112.895 (6)161.8
Symmetry code: (i) x+1, y+1/2, z.
Selected geometric parameters (Å, º) for (II) top
C1A—O2A1.375 (4)C12A—C13A1.430 (3)
O2A—C3A1.371 (3)C13A—N14A1.270 (3)
C3A—C8A1.375 (3)N14A—O15A1.415 (2)
C3A—C4A1.407 (3)C1B—O2B1.418 (3)
C4A—C5A1.350 (3)C13B—N14B1.270 (3)
C5A—C6A1.386 (3)N14B—O15B1.422 (2)
C6A—N9A1.382 (3)C1C—O2C1.421 (3)
C6A—C7A1.405 (3)C13C—N14C1.271 (2)
C7A—C8A1.394 (3)N14C—O15C1.417 (2)
C7A—C12A1.443 (3)C1D—O2D1.423 (4)
N9A—C11A1.352 (3)C13D—N14D1.268 (3)
N9A—C10A1.455 (3)N14D—O15D1.418 (2)
C11A—C12A1.368 (3)
C11A—C12A—C13A123.4 (2)C11C—C12C—C13C123.1 (2)
C11A—C12A—C7A106.5 (2)C11C—C12C—C7C106.3 (2)
C13A—C12A—C7A130.1 (2)C13C—C12C—C7C130.5 (2)
N14A—C13A—C12A124.0 (2)N14C—C13C—C12C123.0 (2)
C13A—N14A—O15A110.9 (2)C13C—N14C—O15C111.0 (2)
C11B—C12B—C13B122.9 (2)C11D—C12D—C13D122.7 (2)
C11B—C12B—C7B106.3 (2)C11D—C12D—C7D106.5 (2)
C13B—C12B—C7B130.8 (2)C13D—C12D—C7D130.8 (2)
N14B—C13B—C12B124.4 (2)N14D—C13D—C12D123.3 (2)
C13B—N14B—O15B110.3 (2)C13D—N14D—O15D110.9 (2)
Hydrogen-bond geometry (Å, º) for (II) top
D—H···AD—HH···AD···AD—H···A
O15A—H15A···N14B0.822.162.882 (3)147.4
O15B—H15B···N14A0.822.042.786 (3)151.3
O15C—H15C···N14Ci0.822.022.755 (3)148.7
O15D—H15D···N14Dii0.822.032.765 (3)148.7
Symmetry codes: (i) x+1, y, z+2; (ii) x+1, y+1, z+2.
Deviations of selected atoms from their respective indole ring planes, using the first nine atoms of each molecule (Å) for molecules A', B', C' and D' of the 5-methoxy compound top
0.0103 (3)C3A-0.019 (2)C3B-0.002 (2)C3C-0.002 (2)C3D
0.0080 (4)C4A-0.015 (2)C4B-0.015 (2)C4C-0.003 (3)C4D
-0.0127 (3)C5A0.010 (2)C5B-0.004 (2)C5C-0.002 (3)C5D
-0.0081 (3)C6A0.020 (3)C6B0.013 (3)C6C0.000 (3)C6D
-0.0074 (2)C7A0.025 (2)C7B0.012 (2)C7C0.004 (2)C7D
-0.0041 (3)C8A0.009 (2)C8B0.012 (2)C8C0.005 (2)C8D
0.0095 (2)N9A-0.003 (2)N9B0.010 (2)N9C0.006 (2)N9D
0.0067 (2)C11A-0.022 (2)C11B-0.008 (2)C11C-0.002 (2)C11D
-0.0023 (2)C12A-0.005 (2)C12B-0.018 (2)C12C-0.006 (2)C12D
0.3622 (7)C1A-0.375 (5)C1B-0.139 (5)C1C0.214 (5)C1D
-0.005 (5)O2A-0.025 (3)O2B0.032 (3)O2C-0.027 (4)O2D
-0.028 (5)C10A-0.021 (5)C10B0.034 (5)C10C-0.059 (5)C10D
-0.007 (4)C13A-0.019 (4)C13B-0.126 (4)C13C-0.075 (4)C13D
-0.082 (5)N14A0.005 (4)N14B-0.216 (4)N14C-0.148 (4)N14D
-0.024 (6)O15A0.021 (5)O15B-0.361 (5)O15C-0.246 (5)O15D
 

Follow Acta Cryst. C
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds