organic compounds
Methyl (2Z)-2-[(2-formyl-3-methyl-1H-indol-1-yl)methyl]-3-(4-methoxyphenyl)prop-2-enoate
aDepartment of Physics, Kalasalingam University, Krishnankoil 626 126, India, bLaboratory of X-ray Crystallography, Indian Institute of Chemical Technology, Hyderabad 500 067, India, and cDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
*Correspondence e-mail: s_selvanayagam@rediffmail.com
In the title indole derivative, C22H21NO4, the dihedral angle between the benzene and pyrrole rings of indole moiety is 1.8 (1)°. The plane of the 4-methoxyphenyl ring is oriented with a dihedral angle of 60.7 (1)° with respect to the plane of the indole moiety. The molecular packing is stabilized by C—H⋯O hydrogen bonds which form a V-shaped chain arrangement along the bc plane of the In addition to this, C—H⋯π and π–π interactions [centroid–centroid distances = 3.8102 (11) and 3.8803(12) Å], which run along the b-axis direction, stabilize the molecular packing.
CCDC reference: 990594
Related literature
For general background to indole derivatives, see: Kaushik et al. (2013); Singh et al. (2000); Andreani et al. (2001); Grinev et al. (1984); Rodriguez et al. (1985). For a related structure, see: Selvanayagam et al. (2008). For the superposition of a related structure, see: Gans & Shalloway (2001)
Experimental
Crystal data
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Data collection: SMART (Bruker, 2001); cell SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2013 and PLATON.
Supporting information
CCDC reference: 990594
10.1107/S1600536814005261/zq2219sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814005261/zq2219Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814005261/zq2219Isup3.cml
POCl3 (1 ml) was added drop wise with stirring to DMF (4.25 ml) at 10–20°C over 20 minutes. Then (E)-methyl 4-(3-methyl-1H-indol-1-yl)-3-(4-methoxy phenyl)but-2-enoate (1 g) in DMF (3 ml) was added slowly with stirring and the mixture was heated. Excess concentrated aqueous solution of NaOAc was added. The mixture was stirred for 30 minutes at 28°C and extracted with AcOEt (3x20ml). The dried (MgSO4) extract after removal of solvent furnished a pale yellow oil (1.10 g), which was chromatographed on a silica gel column. Elution with light petroleum-ether/ethyl acetate (3:1) afforded the product in 80% yield. Single crystals of (I) were obtained by slow evaporation of methanol solution of the title compound at room temperature.
H atoms were placed in idealized positions and allowed to ride on their parent atoms, with C—H distances of 0.93–0.96 Å, and Uiso(H) = 1.5Ueq(methyl C) and Uiso(H) = 1.2Ueq for other C atoms.
Data collection: SMART (Bruker, 2001); cell
SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2013 (Sheldrick, 2008) and PLATON (Spek, 2009).Fig. 1. The molecular structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. | |
Fig. 2. Superposition of (I) (yellow) with the similar reported structure Selvanayagam et al. (2008) (red). | |
Fig. 3. Molecular packing of the title compound, viewed down the c axis; H-bonds are shown as dashed lines·For the sake of clarity, H atoms, not involved in hydrogen bonds, have been omitted | |
Fig. 4. Molecular packing of the title compound, viewed along the a axis; C—H···π interactions are shown as dashed lines·For the sake of clarity, H atoms, not involved in hydrogen bonds, have been omitted | |
Fig. 5. Molecular packing of the title compound, showing π···π interactions. For the sake of clarity, H atoms, not involved in hydrogen bonds, have been omitted |
C22H21NO4 | F(000) = 768 |
Mr = 363.40 | Dx = 1.290 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 12.6009 (13) Å | Cell parameters from 13428 reflections |
b = 10.7458 (11) Å | θ = 2.2–27.7° |
c = 14.8937 (16) Å | µ = 0.09 mm−1 |
β = 111.954 (2)° | T = 292 K |
V = 1870.5 (3) Å3 | Block, colourless |
Z = 4 | 0.20 × 0.18 × 0.16 mm |
Bruker SMART APEX CCD area-detector diffractometer | Rint = 0.030 |
Radiation source: fine-focus sealed tube | θmax = 28.0°, θmin = 1.8° |
ω scans | h = −16→16 |
21494 measured reflections | k = −14→14 |
4462 independent reflections | l = −19→19 |
3214 reflections with I > 2σ(I) |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.052 | H-atom parameters constrained |
wR(F2) = 0.143 | w = 1/[σ2(Fo2) + (0.069P)2 + 0.3592P] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max = 0.001 |
4462 reflections | Δρmax = 0.21 e Å−3 |
247 parameters | Δρmin = −0.15 e Å−3 |
C22H21NO4 | V = 1870.5 (3) Å3 |
Mr = 363.40 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 12.6009 (13) Å | µ = 0.09 mm−1 |
b = 10.7458 (11) Å | T = 292 K |
c = 14.8937 (16) Å | 0.20 × 0.18 × 0.16 mm |
β = 111.954 (2)° |
Bruker SMART APEX CCD area-detector diffractometer | 3214 reflections with I > 2σ(I) |
21494 measured reflections | Rint = 0.030 |
4462 independent reflections |
R[F2 > 2σ(F2)] = 0.052 | 0 restraints |
wR(F2) = 0.143 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.21 e Å−3 |
4462 reflections | Δρmin = −0.15 e Å−3 |
247 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 1.09513 (15) | 0.60014 (19) | 0.38553 (11) | 0.1024 (6) | |
O2 | 0.73093 (13) | 0.23166 (15) | 0.23313 (11) | 0.0890 (5) | |
O3 | 0.83214 (11) | 0.40122 (13) | 0.29526 (9) | 0.0682 (4) | |
O4 | 0.44555 (12) | 0.52878 (12) | −0.32562 (9) | 0.0700 (4) | |
N1 | 0.93920 (10) | 0.46791 (12) | 0.15072 (9) | 0.0437 (3) | |
C1 | 0.97938 (13) | 0.39988 (13) | 0.09250 (12) | 0.0453 (4) | |
C2 | 0.92204 (16) | 0.35281 (16) | 0.00003 (13) | 0.0555 (4) | |
H2 | 0.8437 | 0.3640 | −0.0321 | 0.067* | |
C3 | 0.9859 (2) | 0.28912 (17) | −0.04190 (16) | 0.0710 (6) | |
H3 | 0.9499 | 0.2570 | −0.1039 | 0.085* | |
C4 | 1.1026 (2) | 0.27130 (18) | 0.00578 (19) | 0.0789 (7) | |
H4 | 1.1428 | 0.2267 | −0.0247 | 0.095* | |
C5 | 1.15958 (17) | 0.31737 (18) | 0.09595 (18) | 0.0709 (6) | |
H5 | 1.2379 | 0.3047 | 0.1270 | 0.085* | |
C6 | 1.09796 (14) | 0.38477 (15) | 0.14165 (13) | 0.0534 (4) | |
C7 | 1.12943 (14) | 0.44737 (16) | 0.23098 (13) | 0.0559 (4) | |
C8 | 1.03115 (13) | 0.49785 (15) | 0.23520 (12) | 0.0481 (4) | |
C9 | 1.24838 (17) | 0.4581 (3) | 0.30555 (18) | 0.0886 (7) | |
H9A | 1.2584 | 0.5388 | 0.3352 | 0.133* | |
H9B | 1.3028 | 0.4471 | 0.2751 | 0.133* | |
H9C | 1.2601 | 0.3952 | 0.3541 | 0.133* | |
C10 | 0.81868 (12) | 0.50076 (14) | 0.12346 (12) | 0.0450 (3) | |
H10A | 0.7900 | 0.5348 | 0.0584 | 0.054* | |
H10B | 0.8118 | 0.5646 | 0.1670 | 0.054* | |
C11 | 0.74697 (12) | 0.39005 (14) | 0.12710 (12) | 0.0469 (4) | |
C12 | 0.76846 (14) | 0.33019 (18) | 0.22202 (13) | 0.0571 (4) | |
C13 | 0.8478 (2) | 0.3602 (3) | 0.39105 (15) | 0.0955 (8) | |
H13A | 0.7749 | 0.3565 | 0.3976 | 0.143* | |
H13B | 0.8967 | 0.4176 | 0.4376 | 0.143* | |
H13C | 0.8822 | 0.2791 | 0.4020 | 0.143* | |
C14 | 0.66281 (13) | 0.34297 (16) | 0.05107 (12) | 0.0521 (4) | |
H14 | 0.6321 | 0.2685 | 0.0621 | 0.063* | |
C15 | 0.61153 (12) | 0.39180 (15) | −0.04761 (12) | 0.0483 (4) | |
C16 | 0.57841 (15) | 0.31163 (16) | −0.12596 (13) | 0.0573 (4) | |
H16 | 0.5927 | 0.2270 | −0.1150 | 0.069* | |
C17 | 0.52504 (16) | 0.35310 (17) | −0.21948 (13) | 0.0588 (4) | |
H17 | 0.5059 | 0.2973 | −0.2708 | 0.071* | |
C18 | 0.49998 (14) | 0.47814 (16) | −0.23680 (12) | 0.0514 (4) | |
C19 | 0.53108 (14) | 0.55973 (15) | −0.15976 (13) | 0.0530 (4) | |
H19 | 0.5147 | 0.6440 | −0.1708 | 0.064* | |
C20 | 0.58585 (13) | 0.51745 (15) | −0.06720 (12) | 0.0508 (4) | |
H20 | 0.6064 | 0.5739 | −0.0162 | 0.061* | |
C21 | 0.4105 (3) | 0.4468 (2) | −0.40614 (16) | 0.0957 (8) | |
H21A | 0.4760 | 0.4035 | −0.4086 | 0.144* | |
H21B | 0.3751 | 0.4937 | −0.4646 | 0.144* | |
H21C | 0.3567 | 0.3877 | −0.3996 | 0.144* | |
C22 | 1.01886 (18) | 0.57581 (18) | 0.30950 (14) | 0.0651 (5) | |
H22 | 0.9471 | 0.6098 | 0.2981 | 0.078* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0958 (12) | 0.1354 (16) | 0.0626 (9) | −0.0236 (11) | 0.0141 (8) | −0.0265 (9) |
O2 | 0.0856 (10) | 0.0859 (10) | 0.0928 (11) | −0.0224 (8) | 0.0304 (8) | 0.0320 (8) |
O3 | 0.0729 (8) | 0.0836 (9) | 0.0526 (7) | −0.0043 (7) | 0.0284 (6) | 0.0071 (6) |
O4 | 0.0881 (9) | 0.0592 (8) | 0.0563 (8) | 0.0043 (7) | 0.0197 (7) | −0.0027 (6) |
N1 | 0.0396 (6) | 0.0444 (7) | 0.0481 (7) | −0.0008 (5) | 0.0174 (6) | 0.0023 (5) |
C1 | 0.0491 (8) | 0.0369 (7) | 0.0578 (9) | −0.0016 (6) | 0.0290 (7) | 0.0064 (7) |
C2 | 0.0657 (10) | 0.0494 (9) | 0.0614 (10) | −0.0101 (8) | 0.0351 (9) | −0.0008 (8) |
C3 | 0.0993 (16) | 0.0541 (11) | 0.0823 (13) | −0.0183 (10) | 0.0601 (12) | −0.0107 (9) |
C4 | 0.1000 (17) | 0.0518 (11) | 0.1216 (19) | −0.0048 (10) | 0.0836 (16) | −0.0062 (12) |
C5 | 0.0616 (11) | 0.0558 (11) | 0.1150 (17) | 0.0047 (9) | 0.0556 (12) | 0.0115 (11) |
C6 | 0.0482 (9) | 0.0452 (9) | 0.0750 (12) | 0.0008 (7) | 0.0324 (8) | 0.0135 (8) |
C7 | 0.0436 (8) | 0.0562 (10) | 0.0655 (11) | −0.0032 (7) | 0.0177 (8) | 0.0156 (8) |
C8 | 0.0448 (8) | 0.0475 (8) | 0.0499 (9) | −0.0061 (6) | 0.0152 (7) | 0.0068 (7) |
C9 | 0.0472 (11) | 0.1087 (18) | 0.0958 (17) | −0.0028 (11) | 0.0107 (10) | 0.0148 (14) |
C10 | 0.0420 (8) | 0.0429 (8) | 0.0502 (8) | 0.0020 (6) | 0.0173 (7) | 0.0027 (7) |
C11 | 0.0396 (8) | 0.0479 (9) | 0.0575 (10) | 0.0023 (6) | 0.0232 (7) | 0.0046 (7) |
C12 | 0.0454 (9) | 0.0649 (11) | 0.0660 (11) | 0.0019 (8) | 0.0266 (8) | 0.0137 (9) |
C13 | 0.0927 (16) | 0.144 (2) | 0.0604 (13) | 0.0094 (15) | 0.0402 (12) | 0.0229 (14) |
C14 | 0.0445 (8) | 0.0483 (9) | 0.0676 (11) | −0.0025 (7) | 0.0255 (8) | 0.0015 (8) |
C15 | 0.0373 (7) | 0.0489 (9) | 0.0602 (10) | −0.0023 (6) | 0.0201 (7) | −0.0044 (7) |
C16 | 0.0573 (10) | 0.0437 (9) | 0.0696 (12) | −0.0010 (7) | 0.0221 (9) | −0.0051 (8) |
C17 | 0.0648 (11) | 0.0505 (10) | 0.0601 (11) | −0.0014 (8) | 0.0220 (9) | −0.0133 (8) |
C18 | 0.0484 (9) | 0.0522 (9) | 0.0554 (10) | 0.0004 (7) | 0.0215 (8) | −0.0047 (7) |
C19 | 0.0497 (9) | 0.0432 (8) | 0.0661 (11) | 0.0039 (7) | 0.0216 (8) | −0.0042 (8) |
C20 | 0.0442 (8) | 0.0478 (9) | 0.0598 (10) | 0.0007 (7) | 0.0186 (7) | −0.0122 (7) |
C21 | 0.138 (2) | 0.0762 (15) | 0.0564 (12) | 0.0015 (14) | 0.0173 (13) | −0.0096 (11) |
C22 | 0.0671 (11) | 0.0654 (11) | 0.0594 (11) | −0.0121 (9) | 0.0198 (9) | −0.0061 (9) |
O1—C22 | 1.209 (2) | C9—H9C | 0.9600 |
O2—C12 | 1.196 (2) | C10—C11 | 1.507 (2) |
O3—C12 | 1.327 (2) | C10—H10A | 0.9700 |
O3—C13 | 1.435 (2) | C10—H10B | 0.9700 |
O4—C18 | 1.356 (2) | C11—C14 | 1.328 (2) |
O4—C21 | 1.419 (2) | C11—C12 | 1.483 (2) |
N1—C1 | 1.3678 (19) | C13—H13A | 0.9600 |
N1—C8 | 1.3926 (19) | C13—H13B | 0.9600 |
N1—C10 | 1.4610 (18) | C13—H13C | 0.9600 |
C1—C2 | 1.390 (2) | C14—C15 | 1.464 (2) |
C1—C6 | 1.406 (2) | C14—H14 | 0.9300 |
C2—C3 | 1.371 (3) | C15—C16 | 1.383 (2) |
C2—H2 | 0.9300 | C15—C20 | 1.394 (2) |
C3—C4 | 1.387 (3) | C16—C17 | 1.375 (2) |
C3—H3 | 0.9300 | C16—H16 | 0.9300 |
C4—C5 | 1.358 (3) | C17—C18 | 1.382 (2) |
C4—H4 | 0.9300 | C17—H17 | 0.9300 |
C5—C6 | 1.409 (3) | C18—C19 | 1.379 (2) |
C5—H5 | 0.9300 | C19—C20 | 1.368 (2) |
C6—C7 | 1.409 (3) | C19—H19 | 0.9300 |
C7—C8 | 1.375 (2) | C20—H20 | 0.9300 |
C7—C9 | 1.499 (3) | C21—H21A | 0.9600 |
C8—C22 | 1.442 (3) | C21—H21B | 0.9600 |
C9—H9A | 0.9600 | C21—H21C | 0.9600 |
C9—H9B | 0.9600 | C22—H22 | 0.9300 |
C12—O3—C13 | 117.18 (17) | C14—C11—C10 | 124.63 (15) |
C18—O4—C21 | 117.36 (15) | C12—C11—C10 | 118.58 (14) |
C1—N1—C8 | 108.43 (13) | O2—C12—O3 | 122.96 (17) |
C1—N1—C10 | 123.07 (13) | O2—C12—C11 | 125.11 (18) |
C8—N1—C10 | 128.50 (13) | O3—C12—C11 | 111.89 (15) |
N1—C1—C2 | 130.12 (15) | O3—C13—H13A | 109.5 |
N1—C1—C6 | 107.75 (14) | O3—C13—H13B | 109.5 |
C2—C1—C6 | 122.11 (15) | H13A—C13—H13B | 109.5 |
C3—C2—C1 | 117.19 (18) | O3—C13—H13C | 109.5 |
C3—C2—H2 | 121.4 | H13A—C13—H13C | 109.5 |
C1—C2—H2 | 121.4 | H13B—C13—H13C | 109.5 |
C2—C3—C4 | 121.7 (2) | C11—C14—C15 | 129.15 (15) |
C2—C3—H3 | 119.1 | C11—C14—H14 | 115.4 |
C4—C3—H3 | 119.1 | C15—C14—H14 | 115.4 |
C5—C4—C3 | 121.58 (18) | C16—C15—C20 | 116.97 (16) |
C5—C4—H4 | 119.2 | C16—C15—C14 | 120.29 (15) |
C3—C4—H4 | 119.2 | C20—C15—C14 | 122.56 (15) |
C4—C5—C6 | 118.82 (19) | C17—C16—C15 | 122.12 (16) |
C4—C5—H5 | 120.6 | C17—C16—H16 | 118.9 |
C6—C5—H5 | 120.6 | C15—C16—H16 | 118.9 |
C1—C6—C7 | 107.79 (14) | C16—C17—C18 | 119.69 (16) |
C1—C6—C5 | 118.56 (18) | C16—C17—H17 | 120.2 |
C7—C6—C5 | 133.63 (18) | C18—C17—H17 | 120.2 |
C8—C7—C6 | 106.93 (14) | O4—C18—C19 | 116.06 (15) |
C8—C7—C9 | 127.16 (19) | O4—C18—C17 | 124.70 (15) |
C6—C7—C9 | 125.90 (18) | C19—C18—C17 | 119.24 (16) |
C7—C8—N1 | 109.09 (15) | C20—C19—C18 | 120.44 (16) |
C7—C8—C22 | 128.42 (16) | C20—C19—H19 | 119.8 |
N1—C8—C22 | 122.41 (15) | C18—C19—H19 | 119.8 |
C7—C9—H9A | 109.5 | C19—C20—C15 | 121.53 (15) |
C7—C9—H9B | 109.5 | C19—C20—H20 | 119.2 |
H9A—C9—H9B | 109.5 | C15—C20—H20 | 119.2 |
C7—C9—H9C | 109.5 | O4—C21—H21A | 109.5 |
H9A—C9—H9C | 109.5 | O4—C21—H21B | 109.5 |
H9B—C9—H9C | 109.5 | H21A—C21—H21B | 109.5 |
N1—C10—C11 | 111.97 (12) | O4—C21—H21C | 109.5 |
N1—C10—H10A | 109.2 | H21A—C21—H21C | 109.5 |
C11—C10—H10A | 109.2 | H21B—C21—H21C | 109.5 |
N1—C10—H10B | 109.2 | O1—C22—C8 | 124.7 (2) |
C11—C10—H10B | 109.2 | O1—C22—H22 | 117.7 |
H10A—C10—H10B | 107.9 | C8—C22—H22 | 117.7 |
C14—C11—C12 | 116.77 (15) | ||
C8—N1—C1—C2 | −177.30 (15) | C8—N1—C10—C11 | −108.02 (17) |
C10—N1—C1—C2 | 2.3 (2) | N1—C10—C11—C14 | −117.11 (17) |
C8—N1—C1—C6 | 1.06 (16) | N1—C10—C11—C12 | 64.62 (18) |
C10—N1—C1—C6 | −179.33 (12) | C13—O3—C12—O2 | −5.0 (3) |
N1—C1—C2—C3 | 178.78 (15) | C13—O3—C12—C11 | 172.89 (16) |
C6—C1—C2—C3 | 0.6 (2) | C14—C11—C12—O2 | 13.9 (3) |
C1—C2—C3—C4 | 0.4 (3) | C10—C11—C12—O2 | −167.73 (18) |
C2—C3—C4—C5 | −0.8 (3) | C14—C11—C12—O3 | −163.96 (15) |
C3—C4—C5—C6 | 0.0 (3) | C10—C11—C12—O3 | 14.4 (2) |
N1—C1—C6—C7 | −0.97 (17) | C12—C11—C14—C15 | 170.52 (15) |
C2—C1—C6—C7 | 177.54 (14) | C10—C11—C14—C15 | −7.8 (3) |
N1—C1—C6—C5 | −179.87 (14) | C11—C14—C15—C16 | 142.41 (18) |
C2—C1—C6—C5 | −1.4 (2) | C11—C14—C15—C20 | −42.6 (2) |
C4—C5—C6—C1 | 1.0 (3) | C20—C15—C16—C17 | 1.6 (2) |
C4—C5—C6—C7 | −177.55 (18) | C14—C15—C16—C17 | 176.85 (16) |
C1—C6—C7—C8 | 0.51 (17) | C15—C16—C17—C18 | −2.0 (3) |
C5—C6—C7—C8 | 179.17 (17) | C21—O4—C18—C19 | −178.81 (19) |
C1—C6—C7—C9 | −178.39 (17) | C21—O4—C18—C17 | 1.0 (3) |
C5—C6—C7—C9 | 0.3 (3) | C16—C17—C18—O4 | −178.54 (16) |
C6—C7—C8—N1 | 0.14 (17) | C16—C17—C18—C19 | 1.2 (3) |
C9—C7—C8—N1 | 179.02 (17) | O4—C18—C19—C20 | 179.64 (15) |
C6—C7—C8—C22 | −176.54 (16) | C17—C18—C19—C20 | −0.2 (2) |
C9—C7—C8—C22 | 2.3 (3) | C18—C19—C20—C15 | −0.2 (2) |
C1—N1—C8—C7 | −0.75 (17) | C16—C15—C20—C19 | −0.4 (2) |
C10—N1—C8—C7 | 179.66 (13) | C14—C15—C20—C19 | −175.62 (14) |
C1—N1—C8—C22 | 176.17 (14) | C7—C8—C22—O1 | −6.8 (3) |
C10—N1—C8—C22 | −3.4 (2) | N1—C8—C22—O1 | 176.90 (19) |
C1—N1—C10—C11 | 72.45 (17) |
Cg1 and Cg2 are the centroids of the N1/C1/C6–C8 and C1–C6 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C9—H9A···O1 | 0.96 | 2.53 | 3.033 (3) | 113 |
C14—H14···O2 | 0.93 | 2.41 | 2.789 (2) | 104 |
C10—H10B···O2i | 0.97 | 2.51 | 3.480 (2) | 173 |
C22—H22···O2i | 0.93 | 2.49 | 3.409 (3) | 171 |
C17—H17···Cg1ii | 0.93 | 2.76 | 3.573 (2) | 146 |
C21—H21A···Cg2ii | 0.96 | 2.84 | 3.635 (3) | 140 |
Symmetry codes: (i) −x+3/2, y+1/2, −z+1/2; (ii) x−1/2, −y+1/2, z−1/2. |
Cg1 and Cg2 are the centroids of the N1/C1/C6–C8 and C1–C6 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C9—H9A···O1 | 0.96 | 2.53 | 3.033 (3) | 113.0 |
C14—H14···O2 | 0.93 | 2.41 | 2.789 (2) | 104.1 |
C10—H10B···O2i | 0.97 | 2.51 | 3.480 (2) | 173.2 |
C22—H22···O2i | 0.93 | 2.49 | 3.409 (3) | 171.3 |
C17—H17···Cg1ii | 0.93 | 2.76 | 3.573 (2) | 146 |
C21—H21A···Cg2ii | 0.96 | 2.84 | 3.635 (3) | 140 |
Symmetry codes: (i) −x+3/2, y+1/2, −z+1/2; (ii) x−1/2, −y+1/2, z−1/2. |
Acknowledgements
SS acknowledges the Department of Science and Technology (DST), India, for providing computing facilities under DST–Fast Track Scheme. SS also thanks the Vice Chancellor and management of the Kalasalingam University, Krishnankoil, for their support and encouragement.
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Indole is the parent substance of a large number of important compounds that occur in nature with significant biological activity (Kaushik et al., 2013). Indole derivatives exhibit antibacterial, antifungal (Singh et al., 2000), antitumour (Andreani et al., 2001), antidepressant (Grinev et al., 1984) and anti-inflammatory (Rodriguez et al., 1985) activities. In view of that importance, we have undertaken the crystal structure determination of the title compound, and the results are presented here.
The X-ray study confirmed the molecular structure and atomic connectivity for (I), as illustrated in Fig. 1. The geometry of the indole ring system in the present structure is comparable with the related reported structure (Selvanayagam et al., 2008). Fig. 2 shows a superposition of the indole ring system of (I) with this related reported structure, using Qmol (Gans & Shalloway, 2001); the r.m.s. deviation is 0.016 Å.
The sum of the angles at N1 of the indole ring (360°) is in accordance with sp2 hybridization. The widening of the C14—C15—C20 and N1—C8—C22 bond angles [122.6 (2)° and 122.4 (2)°, respectively] are due to the short contacts H10A···H20 (2.2 Å) and H10B···H22 (2.1 Å).
The indole ring system is planar with a maximum deviation of 0.019 (1) Å for atom C3. The carbaldehyde group atoms (C22 and O1) and methyl atom (C9) deviate 0.111 (1), 0.088 (2) and 0.065 (1) Å, respectively from the best plane of the indole ring. The methoxy group atoms (O4 and C21) deviate -0.015 (1) and -0.040 (1) Å, respectively from the best plane of the methoxy phenyl ring. This ring makes a dihedral angle of 60.7 (1)° with indole ring.
In addition to the van der Waals interactions, the molecular structure is influenced by intramolecular C—H···O interactions (Table 1). In the molecular packing, two C—H···O hydrogen bonds form a V-shaped chain arrangement along 'bc' plane of the unit cell (Fig. 3). In addition to this weak C—H···π and π···π interactions stabilizes the molecular packing (Fig. 4 and Fig. 5).