1-(4-Bromo­phen­yl)-4,5-diphenyl-2-(1H-pyrrol-2-yl)-1H-imidazole

Nagaraj, S.; Loganathan, N.

doi:10.1107/S2414314626001070

organic compounds

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ISSN: 2414-3146

Volume 11| Part 2| February 2026| x260107

https://doi.org/10.1107/S2414314626001070

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1-(4-Bromophenyl)-4,5-diphenyl-2-(1H-pyrrol-2-yl)-1H-imidazole

Seeralan Nagaraj ^a and Nagarajan Loganathan ^a,^b ^*

^aSchool of Chemistry, Bharathidasan University, Tiruchirappalli 620 024, Tamilnadu, India, and ^bUGC Faculty Recharge Programme, New Delhi, India
^*Correspondence e-mail: [email protected]

Edited by R. J. Butcher, Howard University, USA (Received 14 November 2025; accepted 2 February 2026; online 3 February 2026)

The title compound, C₂₅H₁₈BrN₃, crystallizes in the triclinic P1 space group. It is of interest with respect to anticancer activity, antibiotic, antibacterial and antifungal properties. The extended structure features N—H⋯N, C—H⋯N, C—H⋯π, N—H⋯π, C—H⋯Br and C—Br⋯π interactions.

Keywords: crystal structure; Debus–Radziszewski reaction; 1,2,4,5-tetrasubstituted imidazoles; anion–π interactions; C—H⋯Br interactions.

CCDC reference: 2224025

Structure description

Imidazoles are one of the essential building blocks in many natural products and are of importance in the pharmaceutical industry. It is well known that the major constituent of most of the marine sponges contains bromopyrrole-imidazole alkaloids (Forte et al., 2009 ; Lindel et al., 2017 ; Zhang et al., 2017 ). Several metalloenzymes consist of histidine (which contains an imidazole moiety) as one of the amino acids in their protein sequence. In addition, N-substituted imidazoles are vital ingredients in several known pharmacologically active metabolites, namely clotrimazole, ketoconazole, miconazole, oxicanozole (a well-known antibiotic for the treatment of fungal infections), zoledronic acid (used for the treatment of osteoporosis), and nilotinib (an anti-cancer drug) (Yadav et al., 2025 ). Similarly, several 1,2,4,5-tetra-substituted imidazole-based commercial drugs are available in the form of capravirine (anti-viral drug), losartan (angiotension receptor blocker), olmersatan, and medoximil (anti-hypertensive agent) (Gupta et al., 2004 ; Narasimhan et al., 2011 ; Siwach et al., 2021 ).

Herein, we report the structure of a 1,2,4,5-tetra-substituted imidazole, namely, 1-(4-bromophenyl)-4,5-diphenyl-2-(1H-pyrrol-2-yl)-1H-imidazole (1). To achieve this, many methods of synthesis were demonstrated (Zhang et al., 2016 ; Hamdi et al., 2024 ; Parameswari & Jayamoorthy, 2025 ). Among these, a multicomponent Debus–Radziszewski reaction involving benzil, pyrrole-2-carboxaldehyde, 4-bromoaniline and ammonium acetate (1:1:3:3 ratio) in glacial acetic acid medium under overnight reflux condition afforded the title compound (1) as a white solid in very good yield (65–70%).

Compound 1 crystallizes in the triclinic P $[\overline{1}]$ space group. Its bond parameters are in good agreement with those of previously determined 1,2,4,5-tetra-substituted imidazole derivatives (Gayathri et al., 2010a ,b ,c ,d ; Xiao et al., 2012 ; Zhao et al., 2012 ). Fig. 1 shows the molecular structure of 1 in which the four substituents on the imidazole are depicted as I to IV. The central imidazole ring is essentially coplanar with the 2-pyrrole ring [dihedral angle = 3.66 (18)]) while it is almost perpendicular to the 4-bromophenyl ring [88.6 (9)°]. The two phenyl rings attached in the 4- and 5-positions of the imidazole ring are not coplanar with it, subtending dihedral angles of 28.7 (9) and 63.3 (9)°, respectively. Intramolecular C—H⋯N, N—H⋯N (Table 1) and C—H⋯π [C2—H2⋯π_Ph(II) 3.21Å and 134°] interactions occur.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯N1	0.86	2.52	2.774 (3)	98
C6—H6⋯N1	0.93	2.61	2.893 (3)	98
C23—H23⋯N1ⁱ	0.93	2.78	3.470 (3)	132
C24—H24⋯N1ⁱⁱ	0.93	2.98	3.547 (4)	121
Symmetry codes: (i) ; (ii) .

Figure 1
The molecular structure of compound 1 with 50% probability displacement ellipsoids.

In the crystal, C—H⋯N (Table 1), C—H⋯π [C15—H15⋯π_Ph(II) 3.19 Å and 128°; symmetry code: 1 − x, 2 − y, 1 − z]; C18—H18⋯π_pyrrole 3.10 Å and 145°; symmetry code: 1 − x, 1 − y, −z; C25—H25⋯π_imidazole 2.86 Å and 136°; symmetry code: 1 − x, 2 − y, 1 − z] and N—H⋯π [N3—H3A⋯π_Ph(III) 3.09 Å and 148°; symmetry code: 1 + x, y, z] interactions are observed. Both intramolecular and intermolecular interactions are shown in (Fig. 2).

Figure 2
Perspective view of the C—H⋯π and C—H⋯Br interactions.

It is well established that weak C—H⋯halogen bonds (Desiraju et al., 2005 , 2011 ; Mazik et al., 2010 ; Capdevila-Cortada et al., 2015 ) and weak anion–π interactions (Schottel et al., 2008 ) play a significant role in crystal engineering and supramolecular chemistry. Herein, the bromine atom participates in various intermolecular interactions i.e. C—Br⋯π interactions (C17—Br⋯π_pyrrole 4.26 Å and 122° symmetry code: 1 − x, 1 − y, −z) and C—H⋯Br interactions (C11—H11⋯Br1 3.64 Å 92°; symmetry code: x, −1 + y, z; C12—H12⋯Br1 3.288 Å 133°; symmetry code: −1 + x, y, z; C21—H21⋯Br1 3.48 Å and 119°; C22—H22⋯Br1 3.05 Å 139°; symmetry code: −x, 1 − y, −z) and eventually leading to the formation of a two-dimensional pillared network type supramolecular architecture (Fig. 3).

Figure 3
Perspective view of C—H⋯Br interactions and the supramolecular architecture.

Synthesis and crystallization

A mixture of benzil (1.5324 g 7.28 mmol), 2-pyrrolecarbaldehyde (0.6847 g, 7.2 mmol), 4-bromoaniline (4.9602 g, 28.8 mmol) and ammonium acetate (3.7555 g, 28.8 mmol) was dissolved in 35 ml of glacial acetic acid and the mixture was allowed to reflux overnight. The reaction was monitored by TLC; after completion, the reaction was quenched by pouring the solution in to a crushed ice bath, the obtained white precipitate was filtered and purified by column chromatography using silica gel and hexane and ethylacetate (9:1) as eluents. Yield 65–70%, m.p. 232°C. FT–IR (cm⁻¹) 1010(s), 1093(w), 1281(w), 1489(w), 1587(w), 3029(w), 3204 (br).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₂₅H₁₈BrN₃
M_r	440.33
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	300
a, b, c (Å)	9.6044 (9), 9.7662 (7), 12.3705 (11)
α, β, γ (°)	103.837 (3), 92.480 (5), 113.592 (2)
V (Å³)	1019.82 (15)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	2.03
Crystal size (mm)	0.29 × 0.20 × 0.17

Data collection
Diffractometer	Bruker D8 QUEST diffractometer with PHOTON II detector
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 )
T_min, T_max	0.590, 0.724
No. of measured, independent and observed [I > 2σ(I)] reflections	28057, 5046, 3328
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.111, 1.02
No. of reflections	5046
No. of parameters	262
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.70, −0.67
Computer programs: APEX4 and SAINT (Bruker, 2012 ), SHELXT (Sheldrick, 2015a ), SHELXL2019/2 (Sheldrick, 2015b ), ORTEP-3 for Windows (Farrugia, 2012 ), DIAMOND (Brandenburg et al., 2014 ) and publCIF (Westrip, 2010 ).

Structural data

CCDC reference: 2224025

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314626001070/bv4059sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314626001070/bv4059Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314626001070/bv4059Isup3.cml

checkCIF report

Computing details top

1-(4-Bromophenyl)-4,5-diphenyl-2-(1H-pyrrol-2-yl)-1H-imidazole top

Crystal data top

C₂₅H₁₈BrN₃	Z = 2
M_r = 440.33	F(000) = 448
Triclinic, P1	D_x = 1.434 Mg m⁻³
a = 9.6044 (9) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.7662 (7) Å	Cell parameters from 9931 reflections
c = 12.3705 (11) Å	θ = 2.3–23.5°
α = 103.837 (3)°	µ = 2.03 mm⁻¹
β = 92.480 (5)°	T = 300 K
γ = 113.592 (2)°	Block, colourless
V = 1019.82 (15) Å³	0.29 × 0.20 × 0.17 mm

Data collection top

Bruker D8 QUEST diffractometer with PHOTON II detector	R_int = 0.044
Radiation source: i-mu-s microfocus source	θ_max = 28.3°, θ_min = 1.7°
φ and ω scans	h = −12→12
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	k = −13→13
T_min = 0.590, T_max = 0.724	l = −16→16
28057 measured reflections	4 standard reflections every 19 reflections
5046 independent reflections	intensity decay: none
3328 reflections with I > 2σ(I)

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.047	H-atom parameters constrained
wR(F²) = 0.111	w = 1/[σ²(F_o²) + (0.0391P)² + 0.6237P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max = 0.001
5046 reflections	Δρ_max = 0.70 e Å⁻³
262 parameters	Δρ_min = −0.67 e Å⁻³

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. All the non-hydrogen atoms were refined anisotropically using full-matrix least-square procedures while the hydrogen atoms were included in the idealized position and N—H proton was added from the difference Fourier map. C—H bonds were constrained to 0.95 Å for aromatic C—H (with U_iso(H) of 1.2).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Br1	0.17363 (4)	0.77956 (4)	−0.13312 (3)	0.07507 (15)
N1	0.6881 (2)	0.7667 (2)	0.40296 (17)	0.0435 (5)
N2	0.4941 (2)	0.7513 (2)	0.28907 (16)	0.0424 (5)
N3	0.8849 (3)	0.7915 (3)	0.2437 (2)	0.0631 (7)
H3A	0.919538	0.786406	0.307202	0.076*
C1	0.5738 (3)	0.7303 (3)	0.5743 (2)	0.0424 (5)
C2	0.4476 (3)	0.6416 (3)	0.6162 (2)	0.0542 (7)
H2	0.351403	0.591522	0.571249	0.065*
C3	0.4624 (4)	0.6265 (4)	0.7230 (2)	0.0629 (8)
H3	0.376028	0.567672	0.750074	0.076*
C4	0.6027 (4)	0.6970 (4)	0.7900 (2)	0.0664 (9)
H4	0.612151	0.685934	0.862259	0.080*
C5	0.7299 (4)	0.7845 (4)	0.7499 (2)	0.0689 (9)
H5	0.825907	0.831789	0.794895	0.083*
C6	0.7161 (3)	0.8026 (3)	0.6430 (2)	0.0553 (7)
H6	0.802551	0.863354	0.616948	0.066*
C7	0.5633 (3)	0.7454 (3)	0.45918 (19)	0.0403 (5)
C8	0.6437 (3)	0.7692 (3)	0.3020 (2)	0.0419 (5)
C9	0.4418 (3)	0.7368 (3)	0.39117 (19)	0.0399 (5)
C10	0.7427 (3)	0.7854 (3)	0.2166 (2)	0.0464 (6)
C11	0.7341 (4)	0.7976 (4)	0.1089 (2)	0.0619 (8)
H11	0.650583	0.797226	0.067589	0.074*
C12	0.8737 (4)	0.8109 (4)	0.0719 (3)	0.0693 (9)
H12	0.899548	0.820796	0.001732	0.083*
C13	0.9628 (4)	0.8067 (4)	0.1560 (3)	0.0706 (9)
H13	1.061884	0.813235	0.154215	0.085*
C14	0.4130 (3)	0.7570 (3)	0.19131 (19)	0.0406 (5)
C15	0.4253 (3)	0.8973 (3)	0.1795 (2)	0.0466 (6)
H15	0.481108	0.988158	0.237019	0.056*
C16	0.3550 (3)	0.9038 (3)	0.0824 (2)	0.0501 (6)
H16	0.364313	0.998937	0.073592	0.060*
C17	0.2714 (3)	0.7691 (3)	−0.0007 (2)	0.0478 (6)
C18	0.2563 (4)	0.6277 (3)	0.0102 (2)	0.0623 (8)
H18	0.199101	0.536796	−0.046879	0.075*
C19	0.3278 (4)	0.6230 (3)	0.1077 (2)	0.0596 (7)
H19	0.317994	0.527791	0.116641	0.071*
C20	0.2879 (3)	0.7227 (3)	0.41275 (19)	0.0404 (5)
C21	0.1557 (3)	0.5947 (3)	0.3567 (2)	0.0592 (7)
H21	0.161990	0.516775	0.299562	0.071*
C22	0.0139 (3)	0.5807 (4)	0.3844 (3)	0.0688 (8)
H22	−0.074278	0.493345	0.345820	0.083*
C23	0.0017 (3)	0.6925 (4)	0.4671 (3)	0.0624 (8)
H23	−0.094174	0.681746	0.485665	0.075*
C24	0.1309 (4)	0.8209 (4)	0.5229 (3)	0.0706 (9)
H24	0.123314	0.898620	0.579398	0.085*
C25	0.2730 (3)	0.8356 (3)	0.4957 (3)	0.0594 (7)
H25	0.360480	0.923780	0.534372	0.071*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0872 (3)	0.0988 (3)	0.0531 (2)	0.0534 (2)	0.00014 (16)	0.02267 (17)
N1	0.0363 (11)	0.0534 (12)	0.0419 (11)	0.0208 (10)	0.0091 (9)	0.0118 (9)
N2	0.0361 (11)	0.0536 (12)	0.0395 (10)	0.0209 (9)	0.0080 (8)	0.0129 (9)
N3	0.0405 (13)	0.0945 (19)	0.0583 (14)	0.0273 (13)	0.0178 (11)	0.0288 (13)
C1	0.0450 (14)	0.0476 (14)	0.0398 (12)	0.0263 (12)	0.0085 (11)	0.0093 (11)
C2	0.0542 (16)	0.0591 (17)	0.0507 (15)	0.0235 (14)	0.0106 (13)	0.0183 (13)
C3	0.084 (2)	0.0631 (18)	0.0529 (17)	0.0374 (17)	0.0238 (16)	0.0227 (14)
C4	0.105 (3)	0.072 (2)	0.0411 (15)	0.056 (2)	0.0121 (17)	0.0175 (14)
C5	0.076 (2)	0.085 (2)	0.0468 (16)	0.0462 (19)	−0.0089 (15)	0.0020 (15)
C6	0.0500 (16)	0.0701 (18)	0.0473 (15)	0.0307 (14)	0.0055 (12)	0.0099 (13)
C7	0.0353 (13)	0.0457 (14)	0.0398 (12)	0.0184 (11)	0.0071 (10)	0.0092 (10)
C8	0.0380 (13)	0.0442 (13)	0.0435 (13)	0.0176 (11)	0.0101 (11)	0.0114 (11)
C9	0.0372 (13)	0.0433 (13)	0.0388 (12)	0.0174 (11)	0.0077 (10)	0.0100 (10)
C10	0.0437 (14)	0.0490 (15)	0.0480 (14)	0.0199 (12)	0.0135 (11)	0.0147 (11)
C11	0.0630 (18)	0.085 (2)	0.0520 (16)	0.0407 (17)	0.0222 (14)	0.0252 (15)
C12	0.073 (2)	0.082 (2)	0.0587 (18)	0.0331 (18)	0.0336 (17)	0.0251 (16)
C13	0.0494 (18)	0.086 (2)	0.076 (2)	0.0257 (16)	0.0306 (16)	0.0241 (18)
C14	0.0391 (13)	0.0471 (14)	0.0375 (12)	0.0202 (11)	0.0094 (10)	0.0114 (10)
C15	0.0478 (15)	0.0439 (14)	0.0440 (13)	0.0194 (12)	0.0072 (11)	0.0051 (11)
C16	0.0609 (17)	0.0471 (15)	0.0506 (15)	0.0297 (13)	0.0138 (13)	0.0154 (12)
C17	0.0495 (15)	0.0612 (17)	0.0406 (13)	0.0299 (13)	0.0095 (11)	0.0160 (12)
C18	0.078 (2)	0.0446 (16)	0.0490 (16)	0.0191 (14)	−0.0093 (14)	0.0020 (12)
C19	0.075 (2)	0.0434 (15)	0.0551 (16)	0.0234 (14)	−0.0053 (14)	0.0114 (13)
C20	0.0356 (13)	0.0465 (14)	0.0417 (12)	0.0190 (11)	0.0073 (10)	0.0142 (11)
C21	0.0454 (16)	0.0628 (18)	0.0566 (16)	0.0206 (14)	0.0049 (13)	−0.0014 (13)
C22	0.0341 (15)	0.076 (2)	0.078 (2)	0.0147 (14)	0.0019 (14)	0.0055 (17)
C23	0.0400 (16)	0.080 (2)	0.079 (2)	0.0341 (16)	0.0190 (14)	0.0265 (17)
C24	0.0574 (19)	0.0584 (18)	0.094 (2)	0.0293 (16)	0.0272 (17)	0.0063 (17)
C25	0.0427 (15)	0.0496 (16)	0.0750 (19)	0.0157 (13)	0.0168 (14)	0.0037 (14)

Geometric parameters (Å, º) top

Br1—C17	1.897 (2)	C11—H11	0.9300
N1—C8	1.312 (3)	C12—C13	1.336 (5)
N1—C7	1.381 (3)	C12—H12	0.9300
N2—C8	1.373 (3)	C13—H13	0.9300
N2—C9	1.397 (3)	C14—C19	1.369 (4)
N2—C14	1.434 (3)	C14—C15	1.371 (3)
N3—C13	1.348 (4)	C15—C16	1.380 (4)
N3—C10	1.366 (3)	C15—H15	0.9300
N3—H3A	0.8600	C16—C17	1.367 (4)
C1—C2	1.385 (4)	C16—H16	0.9300
C1—C6	1.389 (4)	C17—C18	1.370 (4)
C1—C7	1.469 (3)	C18—C19	1.382 (4)
C2—C3	1.372 (4)	C18—H18	0.9300
C2—H2	0.9300	C19—H19	0.9300
C3—C4	1.366 (5)	C20—C25	1.374 (4)
C3—H3	0.9300	C20—C21	1.377 (4)
C4—C5	1.374 (5)	C21—C22	1.380 (4)
C4—H4	0.9300	C21—H21	0.9300
C5—C6	1.383 (4)	C22—C23	1.353 (4)
C5—H5	0.9300	C22—H22	0.9300
C6—H6	0.9300	C23—C24	1.362 (4)
C7—C9	1.370 (3)	C23—H23	0.9300
C8—C10	1.446 (3)	C24—C25	1.379 (4)
C9—C20	1.471 (3)	C24—H24	0.9300
C10—C11	1.368 (4)	C25—H25	0.9300
C11—C12	1.402 (4)

C8—N1—C7	106.17 (19)	C13—C12—H12	126.2
C8—N2—C9	106.67 (19)	C11—C12—H12	126.2
C8—N2—C14	125.72 (19)	C12—C13—N3	108.6 (3)
C9—N2—C14	127.50 (19)	C12—C13—H13	125.7
C13—N3—C10	109.8 (3)	N3—C13—H13	125.7
C13—N3—H3A	125.1	C19—C14—C15	119.9 (2)
C10—N3—H3A	125.1	C19—C14—N2	120.0 (2)
C2—C1—C6	118.2 (2)	C15—C14—N2	120.1 (2)
C2—C1—C7	122.4 (2)	C14—C15—C16	120.1 (2)
C6—C1—C7	119.3 (2)	C14—C15—H15	120.0
C3—C2—C1	120.9 (3)	C16—C15—H15	120.0
C3—C2—H2	119.6	C17—C16—C15	119.3 (2)
C1—C2—H2	119.6	C17—C16—H16	120.3
C4—C3—C2	120.7 (3)	C15—C16—H16	120.3
C4—C3—H3	119.7	C16—C17—C18	121.4 (2)
C2—C3—H3	119.7	C16—C17—Br1	118.9 (2)
C3—C4—C5	119.4 (3)	C18—C17—Br1	119.7 (2)
C3—C4—H4	120.3	C17—C18—C19	118.7 (2)
C5—C4—H4	120.3	C17—C18—H18	120.7
C4—C5—C6	120.4 (3)	C19—C18—H18	120.7
C4—C5—H5	119.8	C14—C19—C18	120.6 (2)
C6—C5—H5	119.8	C14—C19—H19	119.7
C5—C6—C1	120.3 (3)	C18—C19—H19	119.7
C5—C6—H6	119.9	C25—C20—C21	117.7 (2)
C1—C6—H6	119.9	C25—C20—C9	120.0 (2)
C9—C7—N1	110.3 (2)	C21—C20—C9	122.3 (2)
C9—C7—C1	130.0 (2)	C20—C21—C22	120.7 (3)
N1—C7—C1	119.7 (2)	C20—C21—H21	119.7
N1—C8—N2	111.5 (2)	C22—C21—H21	119.7
N1—C8—C10	122.5 (2)	C23—C22—C21	120.8 (3)
N2—C8—C10	126.0 (2)	C23—C22—H22	119.6
C7—C9—N2	105.3 (2)	C21—C22—H22	119.6
C7—C9—C20	131.4 (2)	C22—C23—C24	119.5 (3)
N2—C9—C20	123.2 (2)	C22—C23—H23	120.2
N3—C10—C11	106.4 (2)	C24—C23—H23	120.2
N3—C10—C8	117.0 (2)	C23—C24—C25	120.0 (3)
C11—C10—C8	136.6 (3)	C23—C24—H24	120.0
C10—C11—C12	107.7 (3)	C25—C24—H24	120.0
C10—C11—H11	126.2	C20—C25—C24	121.3 (3)
C12—C11—H11	126.2	C20—C25—H25	119.3
C13—C12—C11	107.5 (3)	C24—C25—H25	119.3

C6—C1—C2—C3	0.6 (4)	N2—C8—C10—C11	4.6 (5)
C7—C1—C2—C3	178.1 (2)	N3—C10—C11—C12	0.1 (3)
C1—C2—C3—C4	−1.0 (4)	C8—C10—C11—C12	179.9 (3)
C2—C3—C4—C5	0.3 (4)	C10—C11—C12—C13	−0.1 (4)
C3—C4—C5—C6	0.7 (5)	C11—C12—C13—N3	0.0 (4)
C4—C5—C6—C1	−1.1 (4)	C10—N3—C13—C12	0.1 (4)
C2—C1—C6—C5	0.4 (4)	C8—N2—C14—C19	92.0 (3)
C7—C1—C6—C5	−177.2 (2)	C9—N2—C14—C19	−92.4 (3)
C8—N1—C7—C9	−0.7 (3)	C8—N2—C14—C15	−85.6 (3)
C8—N1—C7—C1	177.3 (2)	C9—N2—C14—C15	90.0 (3)
C2—C1—C7—C9	28.5 (4)	C19—C14—C15—C16	−1.6 (4)
C6—C1—C7—C9	−154.0 (3)	N2—C14—C15—C16	176.1 (2)
C2—C1—C7—N1	−149.1 (2)	C14—C15—C16—C17	1.0 (4)
C6—C1—C7—N1	28.4 (3)	C15—C16—C17—C18	−0.2 (4)
C7—N1—C8—N2	0.4 (3)	C15—C16—C17—Br1	179.37 (19)
C7—N1—C8—C10	−178.3 (2)	C16—C17—C18—C19	−0.1 (4)
C9—N2—C8—N1	0.1 (3)	Br1—C17—C18—C19	−179.6 (2)
C14—N2—C8—N1	176.5 (2)	C15—C14—C19—C18	1.3 (4)
C9—N2—C8—C10	178.7 (2)	N2—C14—C19—C18	−176.3 (3)
C14—N2—C8—C10	−4.9 (4)	C17—C18—C19—C14	−0.5 (5)
N1—C7—C9—N2	0.8 (3)	C7—C9—C20—C25	59.9 (4)
C1—C7—C9—N2	−177.0 (2)	N2—C9—C20—C25	−117.1 (3)
N1—C7—C9—C20	−176.5 (2)	C7—C9—C20—C21	−116.3 (3)
C1—C7—C9—C20	5.7 (4)	N2—C9—C20—C21	66.8 (3)
C8—N2—C9—C7	−0.6 (3)	C25—C20—C21—C22	−0.6 (4)
C14—N2—C9—C7	−176.8 (2)	C9—C20—C21—C22	175.6 (3)
C8—N2—C9—C20	177.1 (2)	C20—C21—C22—C23	0.1 (5)
C14—N2—C9—C20	0.8 (4)	C21—C22—C23—C24	0.5 (5)
C13—N3—C10—C11	−0.1 (3)	C22—C23—C24—C25	−0.6 (5)
C13—N3—C10—C8	−179.9 (2)	C21—C20—C25—C24	0.6 (4)
N1—C8—C10—N3	2.7 (4)	C9—C20—C25—C24	−175.7 (3)
N2—C8—C10—N3	−175.7 (2)	C23—C24—C25—C20	0.0 (5)
N1—C8—C10—C11	−177.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···N1	0.86	2.52	2.774 (3)	98
C6—H6···N1	0.93	2.61	2.893 (3)	98
C23—H23···N1ⁱ	0.93	2.78	3.470 (3)	132
C24—H24···N1ⁱⁱ	0.93	2.98	3.547 (4)	121

Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y+2, −z+1.

Funding information

Funding for this research was provided by: Science and Engineering Research Board, India, Early Career Research Award (award No. ECR/2016/001966 to Nagarajan Loganathan); Science and Engineering Research Board, India, EMEQ Scheme (grant No. EEQ2018/001373 to Nagarajan Loganathan); Rashtriya Uchchatar Shiksha Abhiyan, Physical Sciences 2.0 (RUSA 2.0) (grant to Nagarajan Loganathan).

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