In the title compound, the dihedral angles between the 1-methyl indole units (A and B) and the benzoic acid moiety (C) are A/B = 64.87 (7), A/C = 80.92 (8) and B/C = 75.05 (8)°. An intramolecular C—H⋯O interaction arising from the methyne group helps to establish the conformation. In the crystal, 
(8) carboxylic acid inversion dimers linked by pairs of O—H⋯O hydrogen bonds are observed.
Keywords: crystal structure, indole derivatives, benzoic acid
Abstract
In the title compound, C26H22N2O2, the dihedral angles between the 1-methylindole units (A and B) and the benzoic acid moiety (C) are A/B = 64.87 (7), A/C = 80.92 (8) and B/C = 75.05 (8)°. An intramolecular C—H⋯O interaction arising from the methyne group helps to establish the conformation. In the crystal, R 2 2(8) carboxylic acid inversion dimers linked by pairs of O—H⋯O hydrogen bonds are observed. A Hirshfeld surface analysis shows that the greatest contributions are from H⋯H, C⋯H/H⋯C and O⋯H/H⋯O contacts (percentage values = 54.6%, 29.6% and 10.1%, respectively).
Chemical context
Bisindolyl methane and its derivatives are relatively easy to synthesize and show a broad spectrum of potential biological activities: for example, bis(indolyl)imidazole shows antiplasmodial activity towards plasmodium falciparum (Alvarado et al., 2013 ▸). Furthermore, they also have good potential as antibacterial (Imran et al., 2014 ▸; Challa et al., 2017 ▸), antileishmanial (Bharate et al., 2013 ▸), antitumor (Carbone et al., 2013 ▸), antiplatelet (Grumel et al., 2002 ▸) and anticancer (Guo et al., 2010 ▸; Jamsheena et al., 2016 ▸) agents. Oxidized bis(indolyl)methanes containing an acidic hydrogen-bond-donor group and a basic hydrogen-bond-acceptor group can act as selective colorimetric sensors for either F− or HSO4
− in an aprotic solvent (He et al., 2006 ▸). Arylfuryl-bis(indolyl)methanes have selective chromogenic and fluorogenic ratiometric receptors for the mercury ion in aqueous solution (Batista et al., 2014 ▸). As part of our studies in this area, we now report the acid-catalysed condensation reaction between carboxy benzaldehyde and indole to generate the title compound.
Structural commentary
The title compound (Fig. 1 ▸) crystallizes in the triclinic system with space group P
and Z = 2. The molecule consists of two methylated indole ring systems [C8–C17/N1 (A) and C18–C26/N2 (B)] and a benzoic acid [C1–C7 (C)] system linked via the tertiary C8 atom, with dihedral angles between them of A/B = 64.87 (7), A/C = 80.92 (8) and B/C = 75.05 (8)°. Significant torsion angles include C7—C8—C9—C12 [67.3 (3)] and C7—C8—C18—C21 [50.2 (3)°]. An intramolecular C8—H8⋯O1 hydrogen bond (Table 1 ▸) may help to establish the conformation.
Figure 1.
The molecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level.
Table 1. Hydrogen-bond geometry (Å, °).
| D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A |
|---|---|---|---|---|
| O3—H3O⋯O1i | 0.82 (4) | 1.89 (5) | 2.679 (3) | 163 (6) |
| C8—H8⋯O1 | 0.98 | 2.20 | 2.945 (4) | 132 |
Symmetry code: (i) 
.
Supramolecular features
In the crystal of the title compound, neighbouring molecules are connected into dimers with an (8) graph-set motif via pairwise O3—H3O⋯O1 hydrogen bonds (Table 1 ▸, Fig. 2 ▸).
Figure 2.
Crystal packing of the title compound viewed down [100] showing inversion dimers linked by pairs of O—H⋯O hydrogen bonds (dashed lines; Table 1 ▸).
Hirshfeld surface analysis
The Hirshfeld surface and fingerprint (FP) plots for the title compound were generated using CrystalExplorer17 (McKinnon et al., 2007 ▸). A view of the Hirshfeld surface mapped over d norm is shown in Fig. 3 ▸. The intense red spots near the O1-carbonyl and H30-benzoic acid atoms indicate the short interatomic O⋯H/H⋯O contacts relating to the hydrogen bond given in Table 1 ▸. The two-dimensional fingerprint plots for the H⋯H, O⋯H/H⋯O, C⋯H/H⋯C, N⋯H/H⋯N, C⋯C and C⋯N/C⋯N contacts are illustrated in Fig. 4 ▸. The percentage contributions from the different interatomic contact to the Hirshfeld surface are summarized in Table 2 ▸. The fingerprint plot for the H⋯H contacts, which make the largest contribution to the Hirshfeld surface (54.6%), has a broad appearance with a single tip at d e + d i = 2.2 Å. The FP plot for the O⋯H/H⋯O (10.1%) contacts has prominent ‘forceps-like’ tips at d e + d i = 1.7 Å, whereas that for C⋯H/H⋯C contacts (29.6%) shows two pairs of adjacent peaks with d e + d i = 2.6 Å. The other remaining interatomic contacts, which make a small percentage contribution, have a negligible effect on the packing.
Figure 3.
View of the Hirshfeld surface of the title compound mapped over d norm in the range −0.68 to +1.45 au.
Figure 4.
Two-dimensional fingerprint plots of the title compound delineated into H⋯H, O⋯H/H⋯O, C⋯H/H⋯C, N⋯H/H⋯N, C⋯C, C⋯N/N⋯C contacts.
Table 2. Percentage contributions of interatomic contacts to the Hirshfield surface of the title compound.
| Contact | Percentage contribution |
|---|---|
| H⋯H | 54.6 |
| O⋯H/H⋯O | 10.1 |
| C⋯H/H⋯C | 29.6 |
| N⋯H/H⋯N | 1.1 |
| C⋯N/C⋯N | 1.7 |
| C⋯C | 2.8 |
Database survey
A search of the Cambridge Structural Database (Groom et al., 2016 ▸) revealed only seven structures of bis(indole-3-yl) derivatives. These include 3,5-bis(indol-3-yl)-1,2,4-triazin-6(1H,6H)-one methanol solvate (FOLSOP) and 3,6-bis(indol-3-yl)-1,2,4-triazin-4(1H,4H)-one dimethylformamide solvate (FOLTAC; Garg & Stoltz, 2005 ▸), bis(indol-3-yl)(p-tolyl)methane (HODROH; Krishna et al., 1999 ▸), 1,1-bis(indol-3-yl)-1-phenylethane (MEDJEK; Ganesan et al., 2000 ▸), cyclo-N,N′-(α,α′-p-xylyl)bis(indol-3-yl)-N-methylmaleimide (UJALOG), cyclo-N,N′-(α,α′-m-xylyl)bis(indol-3-yl)-N-methylmaleimide (UJALUM) and cyclo-N,N′-[1,11-(3,6,9-trioxaundecyl)]bis(indol-3-yl)-N-methylmaleimide (UJAMAT; Mandl et al., 2003 ▸). Two of these entries (MEDJEK and HODROH) are closely related to the title compound. Two of these entries (MEDJEK and HODROH) are closely related to the title compound with dihedral angles between the 1-methyl indole units of 63.4 (2) and 73.06 (19)° for the two independent molecules in MEDJEK and of 80.8 (1)° in HODROH [64.87 (7)° in the title compound]. In another related compound 4-[bis(1H-indol-3-yl)methyl]benzonitrile (Deng et al., 2011 ▸), the dihedral angle is 72.08 (6)°.
Synthesis and crystallization
Equimolar amounts of 2-carboxybenzaldehyde (3.0 mmol) and 1-methylindole (3.0 mmol) was mixed in a reaction vessel. A few drops of anhydrous acetic acid was added and the mixture was then irradiated in a domestic microwave oven at 100 W for 5 min. The crude product obtained was purified by recrystallization from an acetone–EtOH solvent mixture (v:v = 1:2) to give the pure product in 13.3% yield. IR (ATR, υmax/cm−1): 3058, 2930 (broad, O—H), 1676 (C=O), 1473 (C=C), 1331–1067 (C—O, C—N), 731. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 3.67 (s, 6H, 2 × N-CH3), 6.70 (s, 2H, 2 × H), 6.91 (t, 2H, 2 × ArH), 6.99 (s, 1H, H), 7.11 (t, 2H, 2 × ArH), 7.25–7.30 (m, 3H, J = 7.6, 6.6, 2.2 Hz, ArH and 2 × ArH), 7.35–7.41 (m, 4H,J = 8.0, 5.6, 1.2 Hz, ArH and 2 × ArH), 7.77 (d, 1H, J = 8.0 Hz, ArH) (the OH signal cannot be seen in the 1H NMR sprectrum and hence there are only 21 H atoms in the integration peaks). 13C NMR (101 MHz, DMSO-d6) δ (ppm): 32.7, 34.5, 110.1, 117.9, 118.9, 119.5, 121.6, 126.4, 127.4, 128.6, 130.0, 130.1, 131.3, 131.6, 137.4, 145.2, 170.1.
Refinement
Crystal data, data collection and structure refinement details are summarized in Table 3 ▸. The hydroxy H atom was freely refined. C-bound H atoms were positioned geometrically and refined using a riding model with C—H = 0.93–0.96 and U iso(H) = 1.2–1.5U eq(C).
Table 3. Experimental details.
| Crystal data | |
| Chemical formula | C26H22N2O2 |
| M r | 394.45 |
| Crystal system, space group | Triclinic, P
|
| Temperature (K) | 293 |
| a, b, c (Å) | 8.654 (5), 10.923 (6), 10.964 (5) |
| α, β, γ (°) | 85.85 (2), 82.38 (2), 74.57 (3) |
| V (Å3) | 989.4 (9) |
| Z | 2 |
| Radiation type | Mo Kα |
| μ (mm−1) | 0.08 |
| Crystal size (mm) | 0.55 × 0.39 × 0.30 |
| Data collection | |
| Diffractometer | Bruker PHOTON 100 CMOS |
| Absorption correction | Multi-scan (SADABS; Bruker, 2016 ▸) |
| T min, T max | 0.548, 0.746 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 37627, 4929, 3077 |
| R int | 0.101 |
| (sin θ/λ)max (Å−1) | 0.669 |
| Refinement | |
| R[F 2 > 2σ(F 2)], wR(F 2), S | 0.069, 0.190, 1.03 |
| No. of reflections | 4929 |
| No. of parameters | 277 |
| No. of restraints | 1 |
| H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
| Δρmax, Δρmin (e Å−3) | 0.72, −0.35 |
Supplementary Material
Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989018014160/hb7773sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989018014160/hb7773Isup3.hkl
Supporting information file. DOI: 10.1107/S2056989018014160/hb7773Isup4.cml
Supplementary figures. DOI: 10.1107/S2056989018014160/hb7773sup5.pdf
CCDC reference: 1871874
Additional supporting information: crystallographic information; 3D view; checkCIF report
Acknowledgments
The authors thank Universiti Kebangsaan Malaysia (UKM), the Center of Advanced Materials and Renewable Energy (CAMARR) and the Center for Research and Instrumentation Management (CRIM), UKM, for providing facilities.
supplementary crystallographic information
Crystal data
| C26H22N2O2 | Z = 2 |
| Mr = 394.45 | F(000) = 416 |
| Triclinic, P1 | Dx = 1.324 Mg m−3 |
| a = 8.654 (5) Å | Mo Kα radiation, λ = 0.71076 Å |
| b = 10.923 (6) Å | Cell parameters from 8410 reflections |
| c = 10.964 (5) Å | θ = 2.9–27.3° |
| α = 85.85 (2)° | µ = 0.08 mm−1 |
| β = 82.38 (2)° | T = 293 K |
| γ = 74.57 (3)° | Block, colourless |
| V = 989.4 (9) Å3 | 0.55 × 0.39 × 0.30 mm |
Data collection
| Bruker PHOTON 100 CMOS diffractometer | 3077 reflections with I > 2σ(I) |
| Radiation source: fine-focus sealed tube | Rint = 0.101 |
| φ and ω scans | θmax = 28.4°, θmin = 2.9° |
| Absorption correction: multi-scan (SADABS; Bruker, 2016) | h = −11→11 |
| Tmin = 0.548, Tmax = 0.746 | k = −14→14 |
| 37627 measured reflections | l = −14→14 |
| 4929 independent reflections |
Refinement
| Refinement on F2 | Primary atom site location: structure-invariant direct methods |
| Least-squares matrix: full | Hydrogen site location: mixed |
| R[F2 > 2σ(F2)] = 0.069 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.190 | w = 1/[σ2(Fo2) + (0.0831P)2 + 0.5551P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.03 | (Δ/σ)max < 0.001 |
| 4929 reflections | Δρmax = 0.72 e Å−3 |
| 277 parameters | Δρmin = −0.35 e Å−3 |
| 1 restraint |
Special details
| Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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)
| x | y | z | Uiso*/Ueq | ||
| O1 | 0.1286 (3) | 0.9468 (2) | 0.8786 (2) | 0.0672 (6) | |
| C1 | 0.0635 (3) | 0.8626 (2) | 0.8846 (2) | 0.0418 (6) | |
| H3O | −0.070 (8) | 0.925 (3) | 1.005 (6) | 0.20 (3)* | |
| C26 | 0.8219 (3) | 0.8016 (3) | 0.3643 (3) | 0.0575 (7) | |
| H26A | 0.840826 | 0.738582 | 0.303606 | 0.086* | |
| H26B | 0.901263 | 0.775487 | 0.420976 | 0.086* | |
| H26C | 0.829479 | 0.881343 | 0.324457 | 0.086* | |
| C25 | 0.4893 (3) | 0.9294 (2) | 0.2705 (2) | 0.0465 (6) | |
| H25 | 0.573439 | 0.932437 | 0.209051 | 0.056* | |
| C24 | 0.3315 (4) | 0.9808 (3) | 0.2504 (3) | 0.0556 (7) | |
| H24 | 0.308350 | 1.019279 | 0.174135 | 0.067* | |
| N1 | 0.6152 (2) | 0.6429 (2) | 0.97202 (18) | 0.0427 (5) | |
| N2 | 0.6626 (2) | 0.81578 (19) | 0.43055 (18) | 0.0403 (5) | |
| C2 | 0.1002 (3) | 0.7587 (2) | 0.7937 (2) | 0.0346 (5) | |
| C14 | 0.7258 (3) | 0.3672 (3) | 0.7182 (3) | 0.0517 (7) | |
| H14 | 0.748386 | 0.307509 | 0.657587 | 0.062* | |
| C3 | −0.0168 (3) | 0.6924 (2) | 0.7922 (2) | 0.0420 (6) | |
| H3 | −0.109288 | 0.711578 | 0.848612 | 0.050* | |
| O3 | −0.0538 (3) | 0.8571 (2) | 0.97210 (19) | 0.0631 (6) | |
| C4 | 0.0012 (3) | 0.5995 (2) | 0.7097 (2) | 0.0456 (6) | |
| H4 | −0.076746 | 0.554773 | 0.711828 | 0.055* | |
| C5 | 0.1353 (3) | 0.5732 (3) | 0.6238 (2) | 0.0452 (6) | |
| H5 | 0.147565 | 0.512118 | 0.565909 | 0.054* | |
| C6 | 0.2518 (3) | 0.6386 (2) | 0.6243 (2) | 0.0419 (6) | |
| H6 | 0.341532 | 0.621037 | 0.565193 | 0.050* | |
| C7 | 0.2402 (3) | 0.7292 (2) | 0.7094 (2) | 0.0341 (5) | |
| C21 | 0.3939 (3) | 0.8673 (2) | 0.4803 (2) | 0.0339 (5) | |
| C8 | 0.3842 (3) | 0.7849 (2) | 0.7119 (2) | 0.0332 (5) | |
| H8 | 0.341561 | 0.869135 | 0.746666 | 0.040* | |
| C22 | 0.2345 (3) | 0.9212 (2) | 0.4559 (2) | 0.0436 (6) | |
| H22 | 0.148793 | 0.919612 | 0.516422 | 0.052* | |
| C9 | 0.4939 (3) | 0.7048 (2) | 0.7995 (2) | 0.0347 (5) | |
| C23 | 0.2062 (3) | 0.9762 (3) | 0.3419 (3) | 0.0543 (7) | |
| H23 | 0.100327 | 1.011219 | 0.325564 | 0.065* | |
| C10 | 0.5135 (3) | 0.7397 (2) | 0.9123 (2) | 0.0414 (6) | |
| H10 | 0.464125 | 0.819036 | 0.944587 | 0.050* | |
| C11 | 0.6628 (3) | 0.5408 (2) | 0.8979 (2) | 0.0368 (5) | |
| C13 | 0.6259 (3) | 0.4862 (2) | 0.6972 (2) | 0.0421 (6) | |
| H13 | 0.582726 | 0.506790 | 0.622801 | 0.050* | |
| C12 | 0.5903 (3) | 0.5755 (2) | 0.7882 (2) | 0.0339 (5) | |
| C19 | 0.6294 (3) | 0.7755 (2) | 0.5505 (2) | 0.0371 (5) | |
| H19 | 0.707140 | 0.734204 | 0.601145 | 0.044* | |
| C15 | 0.7928 (3) | 0.3347 (3) | 0.8272 (3) | 0.0542 (7) | |
| H15 | 0.858248 | 0.253282 | 0.839323 | 0.065* | |
| C17 | 0.6653 (4) | 0.6456 (3) | 1.0926 (2) | 0.0616 (8) | |
| H17A | 0.769095 | 0.663417 | 1.083578 | 0.092* | |
| H17B | 0.672004 | 0.564573 | 1.134905 | 0.092* | |
| H17C | 0.587916 | 0.710521 | 1.139210 | 0.092* | |
| C16 | 0.7642 (3) | 0.4213 (3) | 0.9186 (2) | 0.0493 (6) | |
| H16 | 0.811197 | 0.400285 | 0.991351 | 0.059* | |
| C20 | 0.5193 (3) | 0.8728 (2) | 0.3856 (2) | 0.0363 (5) | |
| C18 | 0.4677 (3) | 0.8041 (2) | 0.5851 (2) | 0.0322 (5) |
Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O1 | 0.0693 (14) | 0.0618 (13) | 0.0698 (14) | −0.0252 (11) | 0.0249 (11) | −0.0267 (11) |
| C1 | 0.0343 (12) | 0.0498 (15) | 0.0381 (13) | −0.0080 (11) | −0.0023 (10) | 0.0048 (11) |
| C26 | 0.0394 (14) | 0.0683 (19) | 0.0607 (18) | −0.0173 (13) | 0.0129 (12) | 0.0022 (14) |
| C25 | 0.0609 (16) | 0.0423 (13) | 0.0386 (13) | −0.0200 (12) | −0.0030 (12) | 0.0028 (11) |
| C24 | 0.0698 (19) | 0.0517 (16) | 0.0477 (16) | −0.0171 (14) | −0.0213 (14) | 0.0135 (12) |
| N1 | 0.0414 (11) | 0.0582 (13) | 0.0315 (10) | −0.0179 (10) | −0.0058 (8) | −0.0007 (9) |
| N2 | 0.0317 (10) | 0.0449 (11) | 0.0427 (11) | −0.0119 (8) | 0.0025 (8) | 0.0025 (9) |
| C2 | 0.0281 (10) | 0.0387 (12) | 0.0344 (11) | −0.0053 (9) | −0.0052 (9) | 0.0066 (9) |
| C14 | 0.0551 (16) | 0.0435 (14) | 0.0540 (16) | −0.0087 (12) | −0.0038 (13) | −0.0073 (12) |
| C3 | 0.0290 (11) | 0.0503 (14) | 0.0440 (13) | −0.0097 (10) | 0.0006 (10) | 0.0045 (11) |
| O3 | 0.0614 (13) | 0.0700 (14) | 0.0543 (12) | −0.0209 (11) | 0.0201 (10) | −0.0137 (11) |
| C4 | 0.0379 (13) | 0.0517 (15) | 0.0535 (15) | −0.0237 (11) | −0.0074 (11) | 0.0056 (12) |
| C5 | 0.0428 (13) | 0.0518 (15) | 0.0448 (14) | −0.0182 (11) | −0.0032 (11) | −0.0067 (11) |
| C6 | 0.0327 (12) | 0.0542 (15) | 0.0394 (13) | −0.0144 (11) | 0.0013 (10) | −0.0040 (11) |
| C7 | 0.0287 (10) | 0.0411 (12) | 0.0329 (11) | −0.0104 (9) | −0.0055 (9) | 0.0050 (9) |
| C21 | 0.0348 (11) | 0.0290 (11) | 0.0380 (12) | −0.0089 (9) | −0.0040 (9) | −0.0002 (9) |
| C8 | 0.0275 (10) | 0.0372 (12) | 0.0351 (12) | −0.0096 (9) | −0.0004 (9) | −0.0034 (9) |
| C22 | 0.0373 (12) | 0.0411 (13) | 0.0495 (15) | −0.0047 (10) | −0.0080 (11) | 0.0016 (11) |
| C9 | 0.0292 (11) | 0.0442 (13) | 0.0326 (11) | −0.0147 (9) | 0.0001 (9) | −0.0016 (9) |
| C23 | 0.0486 (15) | 0.0500 (16) | 0.0623 (18) | −0.0049 (12) | −0.0209 (13) | 0.0071 (13) |
| C10 | 0.0375 (12) | 0.0496 (14) | 0.0383 (13) | −0.0154 (11) | 0.0003 (10) | −0.0038 (11) |
| C11 | 0.0326 (11) | 0.0463 (13) | 0.0341 (12) | −0.0174 (10) | −0.0008 (9) | 0.0023 (10) |
| C13 | 0.0420 (13) | 0.0439 (14) | 0.0416 (13) | −0.0127 (11) | −0.0060 (10) | −0.0024 (11) |
| C12 | 0.0290 (10) | 0.0422 (12) | 0.0323 (11) | −0.0144 (9) | −0.0001 (9) | −0.0003 (9) |
| C19 | 0.0323 (11) | 0.0415 (13) | 0.0369 (12) | −0.0106 (10) | −0.0022 (9) | 0.0016 (10) |
| C15 | 0.0528 (16) | 0.0438 (15) | 0.0589 (17) | −0.0042 (12) | −0.0037 (13) | 0.0072 (13) |
| C17 | 0.0698 (19) | 0.087 (2) | 0.0350 (14) | −0.0299 (17) | −0.0130 (13) | −0.0032 (14) |
| C16 | 0.0462 (14) | 0.0571 (16) | 0.0433 (14) | −0.0139 (12) | −0.0085 (11) | 0.0141 (12) |
| C20 | 0.0381 (12) | 0.0321 (11) | 0.0399 (12) | −0.0125 (9) | −0.0021 (10) | −0.0017 (9) |
| C18 | 0.0293 (10) | 0.0304 (11) | 0.0363 (12) | −0.0082 (9) | −0.0009 (9) | −0.0018 (9) |
Geometric parameters (Å, º)
| O1—C1 | 1.193 (3) | C5—H5 | 0.9300 |
| C1—O3 | 1.311 (3) | C6—C7 | 1.384 (3) |
| C1—C2 | 1.507 (4) | C6—H6 | 0.9300 |
| C26—N2 | 1.445 (3) | C7—C8 | 1.529 (3) |
| C26—H26A | 0.9600 | C21—C22 | 1.402 (3) |
| C26—H26B | 0.9600 | C21—C20 | 1.410 (3) |
| C26—H26C | 0.9600 | C21—C18 | 1.431 (3) |
| C25—C24 | 1.371 (4) | C8—C9 | 1.507 (3) |
| C25—C20 | 1.389 (3) | C8—C18 | 1.507 (3) |
| C25—H25 | 0.9300 | C8—H8 | 0.9800 |
| C24—C23 | 1.385 (4) | C22—C23 | 1.370 (4) |
| C24—H24 | 0.9300 | C22—H22 | 0.9300 |
| N1—C11 | 1.368 (3) | C9—C10 | 1.365 (3) |
| N1—C10 | 1.371 (3) | C9—C12 | 1.441 (3) |
| N1—C17 | 1.449 (3) | C23—H23 | 0.9300 |
| N2—C20 | 1.370 (3) | C10—H10 | 0.9300 |
| N2—C19 | 1.375 (3) | C11—C16 | 1.388 (4) |
| C2—C3 | 1.395 (3) | C11—C12 | 1.410 (3) |
| C2—C7 | 1.402 (3) | C13—C12 | 1.394 (3) |
| C14—C13 | 1.379 (4) | C13—H13 | 0.9300 |
| C14—C15 | 1.380 (4) | C19—C18 | 1.358 (3) |
| C14—H14 | 0.9300 | C19—H19 | 0.9300 |
| C3—C4 | 1.373 (4) | C15—C16 | 1.380 (4) |
| C3—H3 | 0.9300 | C15—H15 | 0.9300 |
| O3—H3O | 0.820 (10) | C17—H17A | 0.9600 |
| C4—C5 | 1.374 (3) | C17—H17B | 0.9600 |
| C4—H4 | 0.9300 | C17—H17C | 0.9600 |
| C5—C6 | 1.383 (3) | C16—H16 | 0.9300 |
| O1—C1—O3 | 120.9 (2) | C9—C8—C7 | 108.83 (18) |
| O1—C1—C2 | 124.9 (2) | C18—C8—C7 | 112.70 (18) |
| O3—C1—C2 | 114.1 (2) | C9—C8—H8 | 106.9 |
| N2—C26—H26A | 109.5 | C18—C8—H8 | 106.9 |
| N2—C26—H26B | 109.5 | C7—C8—H8 | 106.9 |
| H26A—C26—H26B | 109.5 | C23—C22—C21 | 119.3 (2) |
| N2—C26—H26C | 109.5 | C23—C22—H22 | 120.3 |
| H26A—C26—H26C | 109.5 | C21—C22—H22 | 120.3 |
| H26B—C26—H26C | 109.5 | C10—C9—C12 | 105.5 (2) |
| C24—C25—C20 | 117.9 (2) | C10—C9—C8 | 125.6 (2) |
| C24—C25—H25 | 121.1 | C12—C9—C8 | 128.7 (2) |
| C20—C25—H25 | 121.1 | C22—C23—C24 | 121.6 (3) |
| C25—C24—C23 | 121.0 (3) | C22—C23—H23 | 119.2 |
| C25—C24—H24 | 119.5 | C24—C23—H23 | 119.2 |
| C23—C24—H24 | 119.5 | C9—C10—N1 | 111.3 (2) |
| C11—N1—C10 | 108.1 (2) | C9—C10—H10 | 124.4 |
| C11—N1—C17 | 125.0 (2) | N1—C10—H10 | 124.4 |
| C10—N1—C17 | 126.9 (2) | N1—C11—C16 | 129.4 (2) |
| C20—N2—C19 | 108.30 (19) | N1—C11—C12 | 108.1 (2) |
| C20—N2—C26 | 126.1 (2) | C16—C11—C12 | 122.5 (2) |
| C19—N2—C26 | 125.6 (2) | C14—C13—C12 | 119.5 (2) |
| C3—C2—C7 | 119.2 (2) | C14—C13—H13 | 120.2 |
| C3—C2—C1 | 116.8 (2) | C12—C13—H13 | 120.2 |
| C7—C2—C1 | 123.9 (2) | C13—C12—C11 | 118.0 (2) |
| C13—C14—C15 | 121.4 (3) | C13—C12—C9 | 135.0 (2) |
| C13—C14—H14 | 119.3 | C11—C12—C9 | 107.0 (2) |
| C15—C14—H14 | 119.3 | C18—C19—N2 | 110.8 (2) |
| C4—C3—C2 | 121.6 (2) | C18—C19—H19 | 124.6 |
| C4—C3—H3 | 119.2 | N2—C19—H19 | 124.6 |
| C2—C3—H3 | 119.2 | C14—C15—C16 | 121.0 (2) |
| C1—O3—H3O | 102 (5) | C14—C15—H15 | 119.5 |
| C3—C4—C5 | 119.5 (2) | C16—C15—H15 | 119.5 |
| C3—C4—H4 | 120.2 | N1—C17—H17A | 109.5 |
| C5—C4—H4 | 120.2 | N1—C17—H17B | 109.5 |
| C4—C5—C6 | 119.2 (2) | H17A—C17—H17B | 109.5 |
| C4—C5—H5 | 120.4 | N1—C17—H17C | 109.5 |
| C6—C5—H5 | 120.4 | H17A—C17—H17C | 109.5 |
| C5—C6—C7 | 122.6 (2) | H17B—C17—H17C | 109.5 |
| C5—C6—H6 | 118.7 | C15—C16—C11 | 117.6 (2) |
| C7—C6—H6 | 118.7 | C15—C16—H16 | 121.2 |
| C6—C7—C2 | 117.7 (2) | C11—C16—H16 | 121.2 |
| C6—C7—C8 | 118.5 (2) | N2—C20—C25 | 130.2 (2) |
| C2—C7—C8 | 123.7 (2) | N2—C20—C21 | 107.6 (2) |
| C22—C21—C20 | 118.0 (2) | C25—C20—C21 | 122.2 (2) |
| C22—C21—C18 | 134.8 (2) | C19—C18—C21 | 106.1 (2) |
| C20—C21—C18 | 107.2 (2) | C19—C18—C8 | 126.7 (2) |
| C9—C8—C18 | 114.13 (18) | C21—C18—C8 | 126.96 (19) |
| C20—C25—C24—C23 | −0.1 (4) | C14—C13—C12—C11 | 1.9 (3) |
| O1—C1—C2—C3 | −161.0 (3) | C14—C13—C12—C9 | −179.8 (2) |
| O3—C1—C2—C3 | 16.6 (3) | N1—C11—C12—C13 | 178.30 (19) |
| O1—C1—C2—C7 | 16.6 (4) | C16—C11—C12—C13 | −1.4 (3) |
| O3—C1—C2—C7 | −165.8 (2) | N1—C11—C12—C9 | −0.5 (2) |
| C7—C2—C3—C4 | −0.5 (3) | C16—C11—C12—C9 | 179.8 (2) |
| C1—C2—C3—C4 | 177.2 (2) | C10—C9—C12—C13 | −178.4 (2) |
| C2—C3—C4—C5 | −1.9 (4) | C8—C9—C12—C13 | 5.4 (4) |
| C3—C4—C5—C6 | 1.7 (4) | C10—C9—C12—C11 | 0.1 (2) |
| C4—C5—C6—C7 | 0.8 (4) | C8—C9—C12—C11 | −176.1 (2) |
| C5—C6—C7—C2 | −3.1 (4) | C20—N2—C19—C18 | 0.3 (3) |
| C5—C6—C7—C8 | 172.9 (2) | C26—N2—C19—C18 | 179.6 (2) |
| C3—C2—C7—C6 | 2.9 (3) | C13—C14—C15—C16 | −1.0 (4) |
| C1—C2—C7—C6 | −174.7 (2) | C14—C15—C16—C11 | 1.5 (4) |
| C3—C2—C7—C8 | −172.9 (2) | N1—C11—C16—C15 | −179.9 (2) |
| C1—C2—C7—C8 | 9.5 (3) | C12—C11—C16—C15 | −0.2 (4) |
| C6—C7—C8—C9 | −90.0 (2) | C19—N2—C20—C25 | 179.3 (2) |
| C2—C7—C8—C9 | 85.8 (3) | C26—N2—C20—C25 | 0.1 (4) |
| C6—C7—C8—C18 | 37.6 (3) | C19—N2—C20—C21 | −0.2 (3) |
| C2—C7—C8—C18 | −146.6 (2) | C26—N2—C20—C21 | −179.4 (2) |
| C20—C21—C22—C23 | 0.4 (3) | C24—C25—C20—N2 | −179.5 (2) |
| C18—C21—C22—C23 | 179.7 (3) | C24—C25—C20—C21 | −0.1 (4) |
| C18—C8—C9—C10 | 125.1 (2) | C22—C21—C20—N2 | 179.5 (2) |
| C7—C8—C9—C10 | −108.1 (2) | C18—C21—C20—N2 | 0.0 (2) |
| C18—C8—C9—C12 | −59.5 (3) | C22—C21—C20—C25 | 0.0 (3) |
| C7—C8—C9—C12 | 67.3 (3) | C18—C21—C20—C25 | −179.5 (2) |
| C21—C22—C23—C24 | −0.6 (4) | N2—C19—C18—C21 | −0.3 (3) |
| C25—C24—C23—C22 | 0.4 (4) | N2—C19—C18—C8 | −174.8 (2) |
| C12—C9—C10—N1 | 0.4 (3) | C22—C21—C18—C19 | −179.2 (3) |
| C8—C9—C10—N1 | 176.70 (19) | C20—C21—C18—C19 | 0.2 (2) |
| C11—N1—C10—C9 | −0.7 (3) | C22—C21—C18—C8 | −4.7 (4) |
| C17—N1—C10—C9 | 179.4 (2) | C20—C21—C18—C8 | 174.7 (2) |
| C10—N1—C11—C16 | −179.6 (2) | C9—C8—C18—C19 | −11.6 (3) |
| C17—N1—C11—C16 | 0.3 (4) | C7—C8—C18—C19 | −136.4 (2) |
| C10—N1—C11—C12 | 0.7 (2) | C9—C8—C18—C21 | 175.0 (2) |
| C17—N1—C11—C12 | −179.4 (2) | C7—C8—C18—C21 | 50.2 (3) |
| C15—C14—C13—C12 | −0.7 (4) |
Hydrogen-bond geometry (Å, º)
| D—H···A | D—H | H···A | D···A | D—H···A |
| O3—H3O···O1i | 0.82 (4) | 1.89 (5) | 2.679 (3) | 163 (6) |
| C8—H8···O1 | 0.98 | 2.20 | 2.945 (4) | 132 |
Symmetry code: (i) −x, −y+2, −z+2.
Percentage contributions of interatomic contacts to the Hirshfeld surface for (I)
| Contact | Percentage contribution |
| H ··· H | 54.6 |
| O ··· H / H ··· O | 10.1 |
| C ··· H / H ··· C | 29.6 |
| N ··· H / H ··· N | 1.1 |
| C ··· N / N ··· C | 1.7 |
| C ··· C | 2.8 |
Funding Statement
This work was funded by Ministry of Higher Education grant FRGS-1-2015-STO1-UKM-02/2. Universiti Kebangsaan Malaysia grants GUP- 2017-086 and DIP-2015-015.
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Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Supplementary Materials
Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989018014160/hb7773sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989018014160/hb7773Isup3.hkl
Supporting information file. DOI: 10.1107/S2056989018014160/hb7773Isup4.cml
Supplementary figures. DOI: 10.1107/S2056989018014160/hb7773sup5.pdf
CCDC reference: 1871874
Additional supporting information: crystallographic information; 3D view; checkCIF report