Synthesis, crystal structure and Hirshfeld surface analysis of [1-(4-bromo­phen­yl)-1H-1,2,3-triazol-4-yl]methyl 2-(4-nitro­phen­oxy)acetate

Hakimov, M.; Khozhimatova, S.; Ortikov, I.; Abdugafurov, I.; Tojiboev, A.

doi:10.1107/S2056989024007436

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Volume 80| Part 8| August 2024| Pages 910-912

https://doi.org/10.1107/S2056989024007436

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Synthesis, crystal structure and Hirshfeld surface analysis of [1-(4-bromophenyl)-1H-1,2,3-triazol-4-yl]methyl 2-(4-nitrophenoxy)acetate

Muminjon Hakimov,^a ^* Shakhnoza Khozhimatova,^b Ilkhomjon Ortikov,^c Ibragimdjan Abdugafurov ^d and Akmaljon Tojiboev ^e,^a

^aNamangan State University, Boburshoh str. 161, Namangan 160107, Uzbekistan, ^bAndijan Machine Building Institute, Bobur Shox Ave 56, Andijan 170119, Uzbekistan, ^cInstitute of the Chemistry of Plant Substances, Uzbekistan Academy of Sciences, Mirzo Ulugbek Str. 77, Tashkent 100170, Uzbekistan, ^dNational University of Uzbekistan, University Str., 4, Tashkent 100174, Uzbekistan, and ^eUniversity of Geological Sciences, Olimlar Str. 64, Tashkent 100170, Uzbekistan
^*Correspondence e-mail: hakimov1094@yahoo.com

Edited by A. S. Batsanov, University of Durham, United Kingdom (Received 26 April 2024; accepted 28 July 2024; online 31 July 2024)

The title compound, C₁₇H₁₃BrN₄O₅, was synthesized by a Cu₂Br₂-catalysed Meldal–Sharpless reaction between 4-nitrophenoxyacetic acid propargyl ether and para-bromophenylazide, and characterized by X-ray structure determination and ¹H NMR spectroscopy. The molecules, with a near-perpendicular orientation of the bromophenyl-triazole and nitrophenoxyacetate fragments, are connected into a three-dimensional network by intermolecular C—H⋯O and C—H⋯N hydrogen bonds (confirmed by Hirshfeld surface analysis), π–π and Br–π interactions.

Keywords: crystal structure; 1,2,3-triazole; click chemistry; hydrogen bonds; Hirshfeld surface analysis.

CCDC reference: 2322358

1. Chemical context

1,3-Dipolar cycloaddition, a reaction between a 1,3-dipole and a dipolarophile to generate a five-membered ring, has been known since the early 20th century, following the discovery of 1,3-dipoles; its mechanism was studied and synthetic applications were developed in the 1960s, primarily through the work of Rolf Huisgen (Bertrand et al., 1994 ; Huisgen, 1963 ). Meldal and Sharpless independently developed a copper(I)-catalysed version of the Huisgen cycloaddition reaction (Tornøe et al., 2002 ; Rostovtsev et al., 2002 ), which earned the name of ‘click chemistry’ for its versatility. They found that only one isomer, 1,4-disubstituted 1,2,3-triazole, was formed from the cycloaddition of terminal alkyne and organic azides under these conditions. The mechanism of the reaction and the role of the Cu^I salt were fully explained. Currently, 1,2,3-triazole derivatives are researched intensively because of their pharmacological and biological activity (Borgati et al., 2013 ; Bozorov et al., 2019 ; Faraz et al., 2017 ; Li et al., 2015 ). In the course these studies, we prepared the title compound 1 by the cross-ring reaction of 4-nitrophenoxyacetic acid propargyl ether with para-bromophenylazide and characterized it by single-crystal X-ray diffraction and NMR spectroscopy.

2. Structural commentary

Compound 1 crystallizes in the monoclinic space group P2₁/n, the asymmetric unit comprising one molecule (Fig. 1) which contains five planar fragments, namely a bromophenyl group, a 1-H-1,2,3-triazole ring, a CH₂OC(=O)CH₂O bridge, phenyl and nitro groups. The interplanar angles between adjacent fragments in this succession are 23.5 (1), 80.3 (1), 19.3 (1) and 6.0 (2)°, respectively. The N17—C12—C11—O10 torsion angle is 97.3 (3)°.

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

3. Supramolecular features

Although the structure contains no classical strong hydrogen bonds, some intermolecular C—H⋯O and C—H⋯N contacts (Table 1) can be identified as hydrogen bonds by Hirshfeld surface analysis (vide infra). They link the molecules into a three-dimensional network (Fig. 2), complemented by π–π stacking between the triazole ring and the brominated phenyl ring [interplanar angle of 8.76 (15)°, Cg1⋯Cg2 distance of 3.723 (16) Å and slippage of 0.917 Å], as well as C24—Br27⋯π interactions [Br27⋯Cg2 = 3.787 (11) Å] involving the same phenyl ring.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C26—H26⋯N17ⁱ	0.93	2.54	3.463 (3)	173
C5—H5⋯O16ⁱⁱ	0.93	2.56	3.493 (3)	176
C8—H8A⋯O16ⁱⁱ	0.97	2.51	3.195 (3)	128
C8—H8B⋯O14ⁱⁱⁱ	0.97	2.54	3.427 (3)	153
C2—H2⋯O16^iv	0.93	2.52	3.287 (3)	140
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) ; (iv) .

Figure 2
Crystal packing of 1, showing hydrogen bonds, π-π- and Br–π interactions as blue, green and red dotted lines, respectively. The centroids of the triazole (Cg1) and brominated phenyl (Cg2) rings are shown by blue and red circles, respectively. H atoms not participating in hydrogen bonds are omitted.

4. Hirshfeld surface analysis

A Hirshfeld surface analysis was performed using CrystalExplorer21 (Spackman et al., 2021 ). The Hirshfeld surface of molecule 1 mapped over d_norm is shown in Fig. 3. The C—H⋯O and C—H⋯N contacts are represented by red spots on the d_norm surface, indicating close interactions (hydrogen bonds). The 2D fingerprint plots (McKinnon et al., 2007 ), show that intermolecular H⋯H and O⋯H/H⋯O contacts make the largest contributions to the total Hirshfeld surface, 23.2% and 25.7%, respectively, other significant contributions being N⋯H/H⋯N (11.7%), Br⋯H/H⋯Br (5.6%) and C⋯H/H⋯C (11.1%) (Fig. 4). The characteristic ‘spikes’ in the N⋯H/H⋯N and especially O⋯H/H⋯O plots are also indicative of hydrogen bonds.

Figure 3
Hirshfeld surface of 1 mapped over d_norm and close intermolecular contacts.

Figure 4
Two-dimensional fingerprint plots of the intermolecular contacts in 1.

5. Database survey

A search of the Cambridge Structural Database (CSD, Version 5.43, last update November 2022; Groom et al., 2016 ) for the 1-(4-bromophenyl)-1H-1,2,3-triazole unit, resulted in four hits, CSD refcodes CEWMID (Tireli et al., 2017 ), HEHNAL (Boechat et al., 2012 ), HOHVAD01 (Li et al., 2015) and XABPIC (Singh et al., 2013 ). In these structures, the dihedral angles between the bromophenyl and triazole rings are comparable to those in the title compound.

6. Synthesis and crystallization

Synthesis of 1.

1.00 g (5 mmol) of para-bromophenylazide, 1.175 g (5 mmol) of prop-2-yn-1-yl-2-(4-nitrophenoxy) acetate, 0.10 g (0.32 mmol) of CuBr and 30 ml of toluene were placed into a flask with a reflux condenser, which was heated on an oil bath at the boiling point of toluene (383 K) for 6 h. The progress of the reaction was monitored by thin-layer chromatography. Over time, a precipitate began to form in the reaction mixture. After 6 h, the reaction was stopped and it was left overnight at room temperature. The precipitate was filtered, dried and recrystallized from ethanol, yielding 1.717 g (79.3%) of 1, m.p. 417–419 K, R_f = 0.55 (system benzene:methanol, 10:1). Colourless single crystals suitable for X-ray diffraction analysis were grown from ethanol at room temperature over two weeks.

In the ¹H NMR spectrum (Fig. S1) of 1 in CDCl₃ the protons of the methylene groups C8H₂ and C11H₂ (see atom numbering in Fig. 1) showed as 2H singlets at 4.76 and 5.43 ppm, respectively. Protons H1 and H5 of the 4-nitrophenoxy group gave a 2H doublet (J = 9.35 Hz) at 6.94 ppm, H2 and H4 a 2H doublet at 8.18 ppm (J = 9.2 Hz). Protons H22 and H26 of the 4-bromophenyl group give a 2H doublet (J = 9.1 Hz) at 7.59 ppm, H23 and H25 a 2H doublet at 7.66 ppm (J = 9.0 Hz). The sole proton of the triazole moiety shows a singlet signal at 8.03 ppm.

7. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. H atoms attached to C were positioned geometrically, with C—H = 0.93 Å for aromatic or C—H = 0.97 Å for methylene C atoms, and were refined as riding with U_iso(H) = 1.2U_eq(C).

Table 2
Experimental details

Crystal data
Chemical formula	C₁₇H₁₃BrN₄O₅
M_r	433.22
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	17.3468 (3), 10.40583 (19), 9.87841 (16)
β (°)	99.4243 (16)
V (Å³)	1759.07 (5)
Z	4
Radiation type	Cu Kα
μ (mm⁻¹)	3.54
Crystal size (mm)	0.6 × 0.4 × 0.2

Data collection
Diffractometer	XtaLAB Synergy, Single source at home/near, HyPix3000
Absorption correction	Multi-scan (CrysAlis PRO; Rigaku OD, 2020 $[Rigaku OD (2020). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ )
T_min, T_max	0.654, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	16655, 3401, 2758
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.616

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.094, 1.06
No. of reflections	3401
No. of parameters	244
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.53
Computer programs: CrysAlis PRO (Rigaku OD, 2020 $[Rigaku OD (2020). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ ), SHELXT2014/1 (Sheldrick, 2015a ), SHELXL2018/3 (Sheldrick, 2015b ), Mercury (Macrae et al., 2020 ) and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 2322358

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989024007436/zv2035sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989024007436/zv2035Isup3.hkl

Figure S1. 1H NMR spectra of compound 1. DOI: https://doi.org/10.1107/S2056989024007436/zv2035sup4.tif

Supporting information file. DOI: https://doi.org/10.1107/S2056989024007436/zv2035Isup4.cml

checkCIF report

Computing details top

[1-(4-Bromophenyl)-1H-1,2,3-triazol-4-yl]methyl 2-(4-nitrophenoxy)acetate top

Crystal data top

C₁₇H₁₃BrN₄O₅	D_x = 1.636 Mg m⁻³
M_r = 433.22	Melting point: 419 K
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54184 Å
a = 17.3468 (3) Å	Cell parameters from 5570 reflections
b = 10.40583 (19) Å	θ = 2.6–70.8°
c = 9.87841 (16) Å	µ = 3.54 mm⁻¹
β = 99.4243 (16)°	T = 293 K
V = 1759.07 (5) Å³	Prism, colourless
Z = 4	0.6 × 0.4 × 0.2 mm
F(000) = 872

Data collection top

XtaLAB Synergy, Single source at home/near, HyPix3000 diffractometer	2758 reflections with I > 2σ(I)
Detector resolution: 10.0000 pixels mm^-1	R_int = 0.044
ω scans	θ_max = 71.6°, θ_min = 2.6°
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2020)	h = −21→21
T_min = 0.654, T_max = 1.000	k = −12→11
16655 measured reflections	l = −11→12
3401 independent reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.094	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0412P)² + 0.3925P] where P = (F_o² + 2F_c²)/3
3401 reflections	(Δ/σ)_max < 0.001
244 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.53 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.

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

	x	y	z	U_iso*/U_eq
Br27	0.23315 (2)	0.34083 (3)	0.13747 (3)	0.05876 (13)
C25	0.33490 (14)	0.4068 (2)	0.3824 (3)	0.0435 (5)
H25	0.312633	0.487975	0.368205	0.052*
O10	0.71928 (9)	0.30539 (17)	0.81015 (16)	0.0444 (4)
O7	0.92280 (10)	0.35886 (19)	0.85518 (17)	0.0513 (5)
O16	0.80463 (11)	0.33428 (18)	1.00422 (17)	0.0526 (5)
N19	0.48779 (11)	0.24275 (18)	0.6241 (2)	0.0393 (4)
O14	1.15099 (13)	0.4209 (2)	0.4317 (2)	0.0723 (6)
O15	1.21345 (13)	0.5260 (2)	0.6045 (3)	0.0725 (6)
N18	0.50303 (15)	0.1230 (2)	0.6747 (3)	0.0599 (6)
N13	1.15860 (13)	0.4594 (2)	0.5506 (3)	0.0531 (6)
N17	0.56280 (15)	0.1328 (2)	0.7739 (3)	0.0629 (7)
C24	0.31006 (14)	0.3080 (2)	0.2928 (2)	0.0423 (5)
C21	0.42602 (13)	0.2639 (2)	0.5120 (2)	0.0377 (5)
C26	0.39253 (14)	0.3849 (2)	0.4926 (3)	0.0413 (5)
H26	0.409094	0.450859	0.554001	0.050*
C9	0.79074 (14)	0.3230 (2)	0.8828 (2)	0.0382 (5)
C3	1.09852 (14)	0.4243 (2)	0.6322 (3)	0.0449 (6)
C6	0.97995 (14)	0.3746 (2)	0.7767 (2)	0.0424 (5)
C20	0.53775 (14)	0.3271 (2)	0.6942 (3)	0.0429 (5)
H20	0.538958	0.415583	0.681321	0.052*
C12	0.58587 (14)	0.2570 (2)	0.7874 (3)	0.0434 (6)
C5	0.97409 (15)	0.3327 (3)	0.6420 (3)	0.0463 (6)
H5	0.930095	0.287661	0.600952	0.056*
C8	0.84817 (14)	0.3220 (3)	0.7848 (2)	0.0441 (6)
H8A	0.850981	0.236529	0.746602	0.053*
H8B	0.831325	0.381126	0.709912	0.053*
C22	0.40085 (15)	0.1648 (2)	0.4226 (3)	0.0441 (6)
H22	0.423542	0.083905	0.436396	0.053*
C23	0.34185 (16)	0.1861 (2)	0.3127 (3)	0.0466 (6)
H23	0.323799	0.119527	0.252980	0.056*
C11	0.65520 (15)	0.2966 (3)	0.8875 (3)	0.0505 (6)
H11A	0.646112	0.379063	0.927913	0.061*
H11B	0.666662	0.233527	0.960297	0.061*
C2	1.10697 (15)	0.4614 (3)	0.7680 (3)	0.0503 (6)
H2	1.152186	0.502689	0.809906	0.060*
C4	1.03377 (15)	0.3580 (2)	0.5696 (3)	0.0470 (6)
H4	1.030331	0.330596	0.479185	0.056*
C1	1.04753 (15)	0.4362 (3)	0.8399 (3)	0.0521 (7)
H1	1.052372	0.460485	0.931496	0.063*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br27	0.0594 (2)	0.0613 (2)	0.05047 (19)	−0.00121 (14)	−0.00636 (14)	−0.00058 (13)
C25	0.0436 (13)	0.0356 (12)	0.0504 (14)	0.0032 (10)	0.0049 (11)	0.0015 (11)
O10	0.0324 (8)	0.0594 (11)	0.0399 (9)	−0.0027 (7)	0.0020 (7)	0.0041 (8)
O7	0.0361 (9)	0.0798 (13)	0.0372 (9)	−0.0098 (8)	0.0034 (7)	−0.0045 (8)
O16	0.0471 (10)	0.0738 (13)	0.0352 (9)	−0.0019 (9)	0.0019 (8)	0.0010 (8)
N19	0.0348 (10)	0.0323 (10)	0.0506 (11)	0.0024 (8)	0.0067 (9)	0.0047 (9)
O14	0.0652 (14)	0.1000 (18)	0.0563 (13)	0.0045 (12)	0.0239 (11)	0.0074 (12)
O15	0.0580 (13)	0.0667 (14)	0.0988 (16)	−0.0162 (11)	0.0307 (12)	−0.0042 (12)
N18	0.0595 (15)	0.0357 (11)	0.0773 (17)	−0.0009 (10)	−0.0099 (12)	0.0114 (11)
N13	0.0463 (13)	0.0515 (13)	0.0643 (15)	0.0071 (10)	0.0171 (11)	0.0111 (11)
N17	0.0587 (15)	0.0465 (13)	0.0766 (17)	0.0007 (11)	−0.0093 (13)	0.0150 (12)
C24	0.0385 (13)	0.0472 (14)	0.0414 (13)	−0.0027 (10)	0.0070 (10)	0.0002 (11)
C21	0.0331 (12)	0.0379 (12)	0.0429 (13)	−0.0016 (9)	0.0090 (10)	0.0016 (10)
C26	0.0402 (13)	0.0347 (12)	0.0484 (14)	−0.0008 (10)	0.0057 (10)	−0.0034 (10)
C9	0.0350 (12)	0.0378 (12)	0.0403 (13)	0.0009 (9)	0.0014 (10)	0.0057 (10)
C3	0.0389 (13)	0.0449 (14)	0.0519 (14)	0.0052 (11)	0.0104 (11)	0.0037 (11)
C6	0.0349 (12)	0.0521 (14)	0.0400 (13)	0.0002 (10)	0.0059 (10)	0.0004 (11)
C20	0.0354 (12)	0.0362 (12)	0.0567 (15)	−0.0028 (10)	0.0058 (11)	0.0029 (11)
C12	0.0333 (12)	0.0481 (14)	0.0496 (14)	0.0001 (10)	0.0094 (10)	0.0033 (11)
C5	0.0384 (13)	0.0558 (16)	0.0430 (13)	−0.0045 (11)	0.0020 (10)	−0.0057 (11)
C8	0.0365 (13)	0.0562 (15)	0.0377 (12)	−0.0058 (11)	0.0007 (10)	−0.0024 (11)
C22	0.0446 (13)	0.0359 (13)	0.0529 (14)	0.0034 (10)	0.0115 (11)	−0.0036 (11)
C23	0.0519 (15)	0.0425 (14)	0.0455 (14)	−0.0045 (11)	0.0084 (12)	−0.0093 (11)
C11	0.0380 (13)	0.0693 (17)	0.0448 (14)	0.0007 (12)	0.0086 (11)	0.0038 (13)
C2	0.0368 (13)	0.0553 (16)	0.0576 (16)	−0.0071 (11)	0.0040 (11)	−0.0067 (13)
C4	0.0441 (14)	0.0547 (16)	0.0422 (13)	0.0015 (12)	0.0071 (11)	−0.0054 (11)
C1	0.0438 (14)	0.0692 (18)	0.0430 (14)	−0.0045 (13)	0.0061 (11)	−0.0098 (13)

Geometric parameters (Å, º) top

Br27—C24	1.892 (2)	C9—C8	1.498 (3)
C25—H25	0.9300	C3—C2	1.381 (4)
C25—C24	1.379 (3)	C3—C4	1.376 (4)
C25—C26	1.371 (3)	C6—C5	1.388 (3)
O10—C9	1.339 (3)	C6—C1	1.391 (3)
O10—C11	1.451 (3)	C20—H20	0.9300
O7—C6	1.365 (3)	C20—C12	1.351 (3)
O7—C8	1.418 (3)	C12—C11	1.485 (4)
O16—C9	1.190 (3)	C5—H5	0.9300
N19—N18	1.353 (3)	C5—C4	1.377 (4)
N19—C21	1.426 (3)	C8—H8A	0.9700
N19—C20	1.344 (3)	C8—H8B	0.9700
O14—N13	1.228 (3)	C22—H22	0.9300
O15—N13	1.226 (3)	C22—C23	1.383 (4)
N18—N17	1.309 (3)	C23—H23	0.9300
N13—C3	1.464 (3)	C11—H11A	0.9700
N17—C12	1.353 (3)	C11—H11B	0.9700
C24—C23	1.385 (4)	C2—H2	0.9300
C21—C26	1.387 (3)	C2—C1	1.370 (3)
C21—C22	1.381 (3)	C4—H4	0.9300
C26—H26	0.9300	C1—H1	0.9300

C24—C25—H25	120.1	N17—C12—C11	121.7 (2)
C26—C25—H25	120.1	C20—C12—N17	108.0 (2)
C26—C25—C24	119.8 (2)	C20—C12—C11	130.3 (2)
C9—O10—C11	116.63 (19)	C6—C5—H5	120.2
C6—O7—C8	116.33 (18)	C4—C5—C6	119.6 (2)
N18—N19—C21	120.4 (2)	C4—C5—H5	120.2
C20—N19—N18	109.9 (2)	O7—C8—C9	109.35 (19)
C20—N19—C21	129.7 (2)	O7—C8—H8A	109.8
N17—N18—N19	106.7 (2)	O7—C8—H8B	109.8
O14—N13—C3	118.1 (2)	C9—C8—H8A	109.8
O15—N13—O14	123.6 (2)	C9—C8—H8B	109.8
O15—N13—C3	118.3 (2)	H8A—C8—H8B	108.3
N18—N17—C12	109.5 (2)	C21—C22—H22	120.0
C25—C24—Br27	119.41 (19)	C21—C22—C23	119.9 (2)
C25—C24—C23	121.1 (2)	C23—C22—H22	120.0
C23—C24—Br27	119.47 (19)	C24—C23—H23	120.5
C26—C21—N19	119.5 (2)	C22—C23—C24	119.0 (2)
C22—C21—N19	120.0 (2)	C22—C23—H23	120.5
C22—C21—C26	120.5 (2)	O10—C11—C12	105.9 (2)
C25—C26—C21	119.7 (2)	O10—C11—H11A	110.6
C25—C26—H26	120.2	O10—C11—H11B	110.6
C21—C26—H26	120.2	C12—C11—H11A	110.6
O10—C9—C8	107.9 (2)	C12—C11—H11B	110.6
O16—C9—O10	124.8 (2)	H11A—C11—H11B	108.7
O16—C9—C8	127.3 (2)	C3—C2—H2	120.6
C2—C3—N13	119.6 (2)	C1—C2—C3	118.8 (2)
C4—C3—N13	118.7 (2)	C1—C2—H2	120.6
C4—C3—C2	121.7 (2)	C3—C4—C5	119.4 (2)
O7—C6—C5	124.1 (2)	C3—C4—H4	120.3
O7—C6—C1	115.9 (2)	C5—C4—H4	120.3
C5—C6—C1	120.0 (2)	C6—C1—H1	119.8
N19—C20—H20	127.1	C2—C1—C6	120.4 (2)
N19—C20—C12	105.8 (2)	C2—C1—H1	119.8
C12—C20—H20	127.1

Br27—C24—C23—C22	176.72 (19)	C21—N19—N18—N17	178.9 (2)
C25—C24—C23—C22	−1.7 (4)	C21—N19—C20—C12	−178.4 (2)
O10—C9—C8—O7	171.6 (2)	C21—C22—C23—C24	1.3 (4)
O7—C6—C5—C4	177.3 (2)	C26—C25—C24—Br27	−177.75 (18)
O7—C6—C1—C2	−177.3 (2)	C26—C25—C24—C23	0.6 (4)
O16—C9—C8—O7	−10.0 (4)	C26—C21—C22—C23	0.1 (4)
N19—N18—N17—C12	0.1 (3)	C9—O10—C11—C12	−171.2 (2)
N19—C21—C26—C25	177.9 (2)	C3—C2—C1—C6	−0.1 (4)
N19—C21—C22—C23	−178.9 (2)	C6—O7—C8—C9	−173.9 (2)
N19—C20—C12—N17	−1.5 (3)	C6—C5—C4—C3	0.2 (4)
N19—C20—C12—C11	176.0 (2)	C20—N19—N18—N17	−1.0 (3)
O14—N13—C3—C2	177.3 (3)	C20—N19—C21—C26	−23.2 (4)
O14—N13—C3—C4	−4.5 (4)	C20—N19—C21—C22	155.8 (2)
O15—N13—C3—C2	−3.1 (4)	C20—C12—C11—O10	−79.9 (3)
O15—N13—C3—C4	175.0 (2)	C5—C6—C1—C2	3.2 (4)
N18—N19—C21—C26	156.9 (2)	C8—O7—C6—C5	−13.6 (4)
N18—N19—C21—C22	−24.1 (3)	C8—O7—C6—C1	166.9 (2)
N18—N19—C20—C12	1.6 (3)	C22—C21—C26—C25	−1.1 (3)
N18—N17—C12—C20	0.9 (3)	C11—O10—C9—O16	−1.6 (4)
N18—N17—C12—C11	−176.8 (2)	C11—O10—C9—C8	176.9 (2)
N13—C3—C2—C1	175.2 (2)	C2—C3—C4—C5	2.9 (4)
N13—C3—C4—C5	−175.2 (2)	C4—C3—C2—C1	−3.0 (4)
N17—C12—C11—O10	97.3 (3)	C1—C6—C5—C4	−3.2 (4)
C24—C25—C26—C21	0.8 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C26—H26···N17ⁱ	0.93	2.54	3.463 (3)	173
C5—H5···O16ⁱⁱ	0.93	2.56	3.493 (3)	176
C8—H8A···O16ⁱⁱ	0.97	2.51	3.195 (3)	128
C8—H8B···O14ⁱⁱⁱ	0.97	2.54	3.427 (3)	153
C2—H2···O16^iv	0.93	2.52	3.287 (3)	140

Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) x, −y+1/2, z−1/2; (iii) −x+2, −y+1, −z+1; (iv) −x+2, −y+1, −z+2.

Acknowledgements

The authors thank the Institute of Bioorganic Chemistry of Academy Sciences of Uzbekistan, Tashkent, Uzbekistan for providing the single-crystal XRD facility.

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