Crystal structure and Hirshfeld analysis of 2-[bis­(1-methyl-1H-indol-3-yl)meth­yl]benzoic acid

Sapari, S.; Wong, S.; Ngatiman, M.F.; Misral, H.; Hasbullah, S.A.

doi:10.1107/S2056989018014160

research communications

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ISSN: 2056-9890

Volume 74| Part 11| November 2018| Pages 1580-1583

https://doi.org/10.1107/S2056989018014160

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Crystal structure and Hirshfeld analysis of 2-[bis(1-methyl-1H-indol-3-yl)methyl]benzoic acid

Suhaila Sapari,^a Sheryn Wong,^a Mohammad Fadzlee Ngatiman,^b Huda Misral ^a and Siti Aishah Hasbullah ^a ^*

^aCentre of Advanced Materials and Renewable Resources, Faculty of Science and Technology, National University of Malaysia, 43600 UKM Bangi, Selangor, Malaysia, and ^bCenter for Research and Instrumentation Management, Universiti Kebangsaan Malaysia, 43600 UKM Bangi, Selangor, Malaysia
^*Correspondence e-mail: aishah80@ukm.edu.my

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 11 September 2018; accepted 8 October 2018; online 16 October 2018)

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, R₂²(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).

Keywords: crystal structure; indole derivatives; benzoic acid.

CCDC reference: 1871874

1. 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.

2. Structural commentary

The title compound (Fig. 1) crystallizes in the triclinic system with space group P $[\overline{1}]$ 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.

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) -x, -y+2, -z+2.

Figure 1
The molecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level.

3. Supramolecular features

In the crystal of the title compound, neighbouring molecules are connected into dimers with an $[R_{2}^{2}]$ (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

4. 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.

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

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.

5. 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)°.

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, υ_max/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.

7. 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 $[\overline{1}]$
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[F² > 2σ(F²)], wR(F²), 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
Δρ_max, Δρ_min (e Å⁻³)	0.72, −0.35
Computer programs: APEX3 and SAINT (Bruker, 2016), SHELXT2014/5 (Sheldrick, 2015a ), SHELXL (Sheldrick, 2015b ), shelXle (Hübschle et al., 2011 ), SHELXTL (Sheldrick, 2008 ), PLATON (Spek, 2009 ), OLEX2 (Dolomanov et al., 2009 ) and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 1871874

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989018014160/hb7773sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989018014160/hb7773Isup3.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989018014160/hb7773Isup4.cml

Supplementary figures. DOI: https://doi.org/10.1107/S2056989018014160/hb7773sup5.pdf

checkCIF report

Computing details top

Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT2014/5 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b), shelXle (Hübschle et al., 2011); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009), OLEX2 (Dolomanov et al., 2009) and publCIF (Westrip, 2010).

2-[Bis(1-methyl-1H-indol-3-yl)methyl]benzoic acid top

Crystal data top

C₂₆H₂₂N₂O₂	Z = 2
M_r = 394.45	F(000) = 416
Triclinic, P1	D_x = 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 top

Bruker PHOTON 100 CMOS diffractometer	3077 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.101
φ and ω scans	θ_max = 28.4°, θ_min = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 2016)	h = −11→11
T_min = 0.548, T_max = 0.746	k = −14→14
37627 measured reflections	l = −14→14
4929 independent reflections

Refinement top

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(F_o²) + (0.0831P)² + 0.5551P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
4929 reflections	Δρ_max = 0.72 e Å⁻³
277 parameters	Δρ_min = −0.35 e Å⁻³
1 restraint

Special details top

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) top

	x	y	z	U_iso*/U_eq
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) top

	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) top

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) top

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 Hirshfield surface of the title compound top

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

Percentage contributions of interatomic contacts to the Hirshfeld surface for (I) top

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

Acknowledgements

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.

Funding information

Funding for this research was provided by: Ministry of Higher Education (grant No. FRGS-1-2015-STO1-UKM-02/2); Universiti Kebangsaan Malaysia (grant No. GUP- 2017-086; grant No. DIP-2015-015).

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