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Journal logoIUCrDATA
ISSN: 2414-3146

2-(5-Bromo-1H-indol-3-yl)-4-(4-bromo­phen­yl)-5-(4-chloro­benzo­yl)-1H-pyrrole-3-carbo­nitrile di­methyl sulfoxide monosolvate

CROSSMARK_Color_square_no_text.svg

aDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India, and bOrganic Chemistry Division, Central Leather Research Institute, Adyar, Chennai 602 020, India
*Correspondence e-mail: aspandian59@gmail.com

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 3 July 2016; accepted 22 July 2016; online 26 July 2016)

In the title solvated compound, C26H14Br2ClN3O·C2H6OS, the indole ring is inclined to the central pyrrole ring by 25.7 (2)°. The chloro­benzene ring and the bromo­benzene rings subtend dihedral angles of 56.5 (2) and 53.4 (2)°, respectively, with the central pyrrole ring. In the crystal, mol­ecules are bridged by N—H⋯O hydrogen bonds, involving the dimethyl sulfoxide solvent mol­ecule, forming chains along [010]. There are no other significant inter­molecular inter­actions present.

3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

Indole structures are considered to be privileged structural motifs due to their ability to bind many receptors within the body (Fuwa & Sasaki, 2009[Fuwa, H. & Sasaki, M. (2009). J. Org. Chem. 74, 212-221.]). Several indole derivatives are in clinical use, such as sunitinib as a tyrosine kinase inhibitor (Oudard et al., 2011[Oudard, S., Beuselinck, B., Decoene, J. & Albers, P. (2011). Cancer Treat. Rev. 37, 178-184.]) or delavirdine as a non-nucleoside reverse transcriptase inhibitor (Beale, 2011[Beale, J. M. (2011). Wilson and Gisvold's Textbook of Organic Medicinal and Pharmaceutical Chemistry, 12th ed., edited by J. M. Beale & J. H. Block, pp. 342-352. Philadelphia: Lippincott Williams and Wilkins.]). Indole derivatives are known to exhibit biological activities such as anti-proliferative (Parrino et al., 2015[Parrino, B., Carbone, A., Di Vita, G., Ciancimino, C., Attanzio, A., Spano, V., Montalbano, A., Barraja, P., Tesoriere, L., Livera, M. A., Diana, P. & Cirrincione, G. (2015). Mar. Drugs, 13, 1901-1924.]), potential mushroom tyrosinase inhibition (Ferro et al., 2015[Ferro, S., Certo, G., De Luca, L., Germanò, M. P., Rapisarda, A. & Gitto, R. (2015). J. Enzyme Inhib. Med. Chem. pp. 1-6.]), anti-inflammatory (Chen et al., 2015[Chen, Y. R., Tseng, C. H., Chen, Y. L., Hwang, T. L. & Tzeng, C. C. (2015). Int. J. Mol. Sci. 16, 6532-6544.]) and anti-tumor (Ma et al., 2015[Ma, J., Bao, G., Wang, L., Li, W., Xu, B., Du, B., Lv, J., Zhai, X. & Gong, P. (2015). Eur. J. Med. Chem. 96, 173-186.]). As part of our studies of indole derivatives, we have synthesized the title compound and report herein on its crystal structure.

In the title compound, Fig. 1[link], the indole ring system is twisted away from the central pyrrole ring by 25.7 (2)°. The C16—C17—N3 bond angle of 178.3 (5)° indicates the linear character of the cyano group, a feature observed in carbo­nitrile compounds. In the benzene ring of the indole ring system, the endocyclic angle at C26 is contracted to 117.8 (4)°, while the angle at C21 is expanded to 122.6 (4)°. This would appear to be a real effect caused by the fusion of the pyrrole ring with the benzene ring resulting in an angular distortion. The chloro­benzene (C1–C6) and bromo­benzene (C10–C15) rings subtend dihedral angles of 56.5 (2)° and 53.4 (2)°, respectively, with the central pyrrole ring.

[Figure 1]
Figure 1
The mol­ecular structure of the title compound, showing the atom labelling. Displacement ellipsoids are drawn at the 30% probability level.

In the crystal, mol­ecules are bridged by N—H⋯O hydrogen bonds involving the dimethyl sulfoxide solvent mol­ecule, forming chains along [010], see Table 1[link] and Fig. 2[link]. There are no other significant inter­molecular inter­actions present.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1⋯O2 0.86 2.08 2.812 (4) 143
N2—H2⋯O2i 0.86 1.96 2.813 (4) 170
Symmetry code: (i) [-x+{\script{5\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].
[Figure 2]
Figure 2
A view along the b axis of the crystal packing of the title compound. The hydrogen bonds are shown as dashed lines (see Table 1[link]), and for clarity C-bound H atoms have been omitted.

Synthesis and crystallization

To a stirred mixture of 4-bromo­benzaldehyde 1 (1.0 mmol), 3-(5-bromo-1H-indol-3-yl)-3-oxo­propane­nitrile 2 (1.0 mmol) and 4-chloro­phenacyl­azide 3 (1.0 mmol) in H2O (3 ml), piperidine (0.25 mmol) was added at 353 K. The turbid solution slowly turned into a clear solution, followed by the formation of a solid after 30 min. After completion of the reaction, as indicated by TLC, the solid was filtered and washed with a PE–EtOAc mixture (1:1 ratio, v/v, 5 ml) to give the title compound (yield 91%), which was recrystallized from EtOH solution to give yellow crystals on slow evaporation of the solvent.

Refinement

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

Table 2
Experimental details

Crystal data
Chemical formula C26H14Br2ClN3O·C2H6OS
Mr 657.80
Crystal system, space group Monoclinic, P21/n
Temperature (K) 293
a, b, c (Å) 12.4962 (12), 12.8055 (10), 17.6834 (17)
β (°) 92.820 (3)
V3) 2826.3 (4)
Z 4
Radiation type Mo Kα
μ (mm−1) 3.07
Crystal size (mm) 0.20 × 0.19 × 0.17
 
Data collection
Diffractometer Bruker SMART APEXII CCD
Absorption correction Multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.])
Tmin, Tmax 0.547, 0.594
No. of measured, independent and observed [I > 2σ(I)] reflections 29776, 4972, 3236
Rint 0.054
(sin θ/λ)max−1) 0.595
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.070, 0.107, 1.15
No. of reflections 4972
No. of parameters 334
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.59, −0.40
Computer programs: APEX2 and SAINT (Bruker, 2008[Bruker (2008). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]), SHELXS97 and SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Structural data


Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

2-(5-Bromo-1H-indol-3-yl)-4-(4-bromophenyl)-5-(4-chlorobenzoyl)-1H-pyrrole-3-carbonitrile dimethyl sulfoxide monosolvate top
Crystal data top
C26H14Br2ClN3O·C2H6OSF(000) = 1312
Mr = 657.80Dx = 1.546 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 3236 reflections
a = 12.4962 (12) Åθ = 2.0–25.0°
b = 12.8055 (10) ŵ = 3.07 mm1
c = 17.6834 (17) ÅT = 293 K
β = 92.820 (3)°Block, yellow
V = 2826.3 (4) Å30.20 × 0.19 × 0.17 mm
Z = 4
Data collection top
Bruker SMART APEXII CCD
diffractometer
4972 independent reflections
Radiation source: fine-focus sealed tube3236 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.054
ω and φ scansθmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
h = 1414
Tmin = 0.547, Tmax = 0.594k = 1515
29776 measured reflectionsl = 2021
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.070Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107H-atom parameters constrained
S = 1.15 w = 1/[σ2(Fo2) + (0.0239P)2 + 4.3884P]
where P = (Fo2 + 2Fc2)/3
4972 reflections(Δ/σ)max = 0.001
334 parametersΔρmax = 0.59 e Å3
0 restraintsΔρmin = 0.40 e Å3
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 > 2sigma(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
xyzUiso*/Ueq
C11.3650 (3)0.7573 (3)0.1460 (3)0.0423 (12)
H1A1.37150.71430.18830.051*
C21.4030 (4)0.8589 (4)0.1498 (3)0.0499 (13)
H2A1.43450.88490.19470.060*
C31.3936 (4)0.9203 (4)0.0868 (4)0.0529 (14)
C41.3434 (4)0.8858 (4)0.0210 (3)0.0563 (15)
H41.33550.92990.02070.068*
C51.3050 (4)0.7857 (4)0.0172 (3)0.0486 (13)
H51.27020.76180.02720.058*
C61.3176 (3)0.7199 (3)0.0791 (3)0.0368 (11)
C71.2789 (3)0.6105 (3)0.0726 (3)0.0389 (11)
C81.3422 (3)0.5262 (3)0.1073 (2)0.0320 (10)
C91.4510 (3)0.5131 (3)0.1266 (2)0.0310 (10)
C101.5384 (3)0.5894 (3)0.1181 (2)0.0323 (10)
C111.5531 (3)0.6405 (3)0.0511 (3)0.0412 (11)
H111.51100.62230.00830.049*
C121.6288 (4)0.7183 (4)0.0458 (3)0.0486 (13)
H121.63790.75240.00010.058*
C131.6907 (4)0.7445 (4)0.1096 (3)0.0490 (13)
C141.6812 (3)0.6930 (4)0.1768 (3)0.0487 (13)
H141.72490.71030.21900.058*
C151.6052 (3)0.6148 (3)0.1807 (3)0.0421 (12)
H151.59880.57860.22590.050*
C161.4618 (3)0.4099 (3)0.1543 (2)0.0305 (10)
C171.5598 (4)0.3568 (4)0.1722 (3)0.0414 (12)
C181.3605 (3)0.3633 (3)0.1538 (2)0.0297 (10)
C191.3286 (3)0.2625 (3)0.1812 (2)0.0317 (10)
C201.3851 (3)0.2061 (3)0.2357 (2)0.0370 (11)
H201.44830.22820.26070.044*
C211.2458 (3)0.1067 (3)0.2000 (2)0.0346 (11)
C221.2373 (3)0.1996 (3)0.1580 (2)0.0307 (10)
C231.1506 (3)0.2111 (3)0.1054 (2)0.0370 (11)
H231.14290.27130.07610.044*
C241.0777 (3)0.1317 (4)0.0981 (3)0.0440 (12)
C251.0879 (4)0.0392 (4)0.1398 (3)0.0504 (13)
H251.03670.01320.13300.060*
C261.1730 (4)0.0255 (3)0.1906 (3)0.0447 (12)
H261.18170.03630.21790.054*
C270.9319 (5)0.5805 (5)0.0966 (4)0.088 (2)
H27A0.98150.62270.07020.132*
H27B0.92440.60820.14650.132*
H27C0.86350.58080.06940.132*
C280.8771 (5)0.3945 (6)0.1528 (4)0.108 (3)
H28A0.89180.32180.16130.162*
H28B0.81070.40190.12350.162*
H28C0.87180.42930.20050.162*
N11.2906 (3)0.4344 (2)0.12369 (19)0.0323 (9)
H11.22310.42370.11580.039*
N21.3361 (3)0.1139 (3)0.2479 (2)0.0415 (10)
H21.35760.06740.28030.050*
N31.6377 (3)0.3126 (3)0.1851 (3)0.0713 (14)
O11.1943 (3)0.5897 (3)0.0367 (2)0.0657 (11)
O21.0750 (2)0.4536 (2)0.16015 (17)0.0458 (8)
Cl11.44831 (14)1.04501 (10)0.09004 (10)0.0869 (6)
Br10.95687 (4)0.14674 (5)0.03007 (4)0.0779 (2)
Br21.79124 (5)0.85467 (5)0.10269 (4)0.0916 (3)
S0.98089 (9)0.45031 (11)0.10350 (8)0.0537 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.047 (3)0.035 (3)0.046 (3)0.004 (2)0.015 (2)0.004 (2)
C20.057 (3)0.040 (3)0.054 (3)0.002 (3)0.022 (3)0.013 (3)
C30.052 (3)0.029 (3)0.081 (4)0.002 (2)0.037 (3)0.000 (3)
C40.057 (3)0.045 (3)0.068 (4)0.008 (3)0.016 (3)0.023 (3)
C50.040 (3)0.046 (3)0.059 (4)0.005 (2)0.001 (2)0.013 (3)
C60.031 (2)0.030 (2)0.050 (3)0.003 (2)0.005 (2)0.008 (2)
C70.035 (3)0.038 (3)0.044 (3)0.001 (2)0.003 (2)0.007 (2)
C80.032 (2)0.029 (2)0.035 (3)0.0015 (19)0.001 (2)0.002 (2)
C90.030 (2)0.035 (3)0.028 (3)0.0016 (19)0.003 (2)0.004 (2)
C100.027 (2)0.034 (2)0.037 (3)0.0016 (19)0.005 (2)0.002 (2)
C110.038 (3)0.046 (3)0.040 (3)0.004 (2)0.004 (2)0.005 (3)
C120.050 (3)0.051 (3)0.046 (3)0.005 (3)0.017 (3)0.008 (3)
C130.038 (3)0.045 (3)0.065 (4)0.010 (2)0.012 (3)0.005 (3)
C140.039 (3)0.055 (3)0.052 (4)0.013 (2)0.006 (2)0.001 (3)
C150.038 (3)0.048 (3)0.040 (3)0.007 (2)0.001 (2)0.006 (2)
C160.024 (2)0.034 (2)0.034 (3)0.0017 (19)0.0025 (19)0.000 (2)
C170.033 (3)0.045 (3)0.047 (3)0.003 (2)0.003 (2)0.011 (2)
C180.030 (2)0.029 (2)0.030 (3)0.003 (2)0.0008 (19)0.002 (2)
C190.028 (2)0.030 (2)0.038 (3)0.0032 (19)0.003 (2)0.002 (2)
C200.034 (3)0.036 (3)0.041 (3)0.000 (2)0.000 (2)0.002 (2)
C210.036 (3)0.034 (3)0.035 (3)0.001 (2)0.011 (2)0.003 (2)
C220.029 (2)0.030 (2)0.033 (3)0.0021 (19)0.007 (2)0.002 (2)
C230.037 (3)0.033 (3)0.041 (3)0.005 (2)0.001 (2)0.000 (2)
C240.032 (3)0.042 (3)0.057 (3)0.000 (2)0.002 (2)0.008 (3)
C250.044 (3)0.047 (3)0.060 (4)0.017 (2)0.006 (3)0.009 (3)
C260.053 (3)0.037 (3)0.045 (3)0.008 (2)0.014 (3)0.004 (2)
C270.074 (4)0.091 (5)0.097 (5)0.037 (4)0.022 (4)0.006 (4)
C280.060 (4)0.153 (7)0.112 (6)0.043 (4)0.013 (4)0.005 (5)
N10.0240 (18)0.030 (2)0.042 (2)0.0013 (16)0.0044 (16)0.0012 (17)
N20.045 (2)0.040 (2)0.039 (2)0.0005 (18)0.0018 (19)0.0119 (18)
N30.035 (3)0.071 (3)0.108 (4)0.011 (2)0.000 (3)0.019 (3)
O10.047 (2)0.055 (2)0.092 (3)0.0101 (17)0.034 (2)0.021 (2)
O20.0327 (17)0.0505 (19)0.053 (2)0.0011 (14)0.0076 (15)0.0094 (16)
Cl10.1126 (13)0.0388 (8)0.1155 (14)0.0208 (8)0.0667 (11)0.0138 (8)
Br10.0487 (3)0.0751 (4)0.1063 (5)0.0023 (3)0.0312 (3)0.0132 (4)
Br20.0821 (5)0.0819 (5)0.1114 (6)0.0496 (4)0.0096 (4)0.0078 (4)
S0.0351 (7)0.0641 (9)0.0608 (9)0.0025 (6)0.0066 (6)0.0133 (7)
Geometric parameters (Å, º) top
C1—C61.383 (6)C16—C171.423 (6)
C1—C21.386 (6)C17—N31.139 (5)
C1—H1A0.9300C18—N11.352 (5)
C2—C31.365 (7)C18—C191.443 (6)
C2—H2A0.9300C19—C201.371 (5)
C3—C41.367 (7)C19—C221.440 (5)
C3—Cl11.737 (5)C20—N21.353 (5)
C4—C51.370 (6)C20—H200.9300
C4—H40.9300C21—N21.380 (5)
C5—C61.384 (6)C21—C261.386 (6)
C5—H50.9300C21—C221.405 (6)
C6—C71.485 (6)C22—C231.400 (5)
C7—O11.235 (5)C23—C241.368 (6)
C7—C81.456 (6)C23—H230.9300
C8—N11.379 (5)C24—C251.397 (6)
C8—C91.395 (5)C24—Br11.893 (4)
C9—C161.414 (6)C25—C261.370 (6)
C9—C101.479 (6)C25—H250.9300
C10—C111.373 (6)C26—H260.9300
C10—C151.392 (6)C27—S1.777 (6)
C11—C121.381 (6)C27—H27A0.9600
C11—H110.9300C27—H27B0.9600
C12—C131.377 (6)C27—H27C0.9600
C12—H120.9300C28—S1.750 (6)
C13—C141.368 (6)C28—H28A0.9600
C13—Br21.898 (4)C28—H28B0.9600
C14—C151.384 (6)C28—H28C0.9600
C14—H140.9300N1—H10.8600
C15—H150.9300N2—H20.8600
C16—C181.399 (5)O2—S1.508 (3)
C6—C1—C2119.9 (4)N1—C18—C16106.4 (3)
C6—C1—H1A120.0N1—C18—C19123.5 (4)
C2—C1—H1A120.0C16—C18—C19130.1 (4)
C3—C2—C1119.0 (5)C20—C19—C22106.3 (4)
C3—C2—H2A120.5C20—C19—C18124.5 (4)
C1—C2—H2A120.5C22—C19—C18129.3 (4)
C2—C3—C4121.8 (4)N2—C20—C19110.5 (4)
C2—C3—Cl1119.0 (5)N2—C20—H20124.7
C4—C3—Cl1119.2 (4)C19—C20—H20124.7
C3—C4—C5119.3 (5)N2—C21—C26129.5 (4)
C3—C4—H4120.3N2—C21—C22107.9 (4)
C5—C4—H4120.3C26—C21—C22122.6 (4)
C4—C5—C6120.3 (5)C23—C22—C21118.5 (4)
C4—C5—H5119.8C23—C22—C19135.0 (4)
C6—C5—H5119.8C21—C22—C19106.5 (3)
C1—C6—C5119.5 (4)C24—C23—C22118.3 (4)
C1—C6—C7121.2 (4)C24—C23—H23120.9
C5—C6—C7119.3 (4)C22—C23—H23120.9
O1—C7—C8119.4 (4)C23—C24—C25122.5 (4)
O1—C7—C6120.7 (4)C23—C24—Br1119.4 (4)
C8—C7—C6119.9 (4)C25—C24—Br1118.1 (3)
N1—C8—C9107.8 (3)C26—C25—C24120.1 (4)
N1—C8—C7118.1 (4)C26—C25—H25119.9
C9—C8—C7134.0 (4)C24—C25—H25119.9
C8—C9—C16105.8 (3)C25—C26—C21117.8 (4)
C8—C9—C10127.7 (4)C25—C26—H26121.1
C16—C9—C10126.4 (4)C21—C26—H26121.1
C11—C10—C15118.3 (4)S—C27—H27A109.5
C11—C10—C9122.2 (4)S—C27—H27B109.5
C15—C10—C9119.4 (4)H27A—C27—H27B109.5
C10—C11—C12121.6 (4)S—C27—H27C109.5
C10—C11—H11119.2H27A—C27—H27C109.5
C12—C11—H11119.2H27B—C27—H27C109.5
C13—C12—C11118.6 (5)S—C28—H28A109.5
C13—C12—H12120.7S—C28—H28B109.5
C11—C12—H12120.7H28A—C28—H28B109.5
C14—C13—C12121.7 (4)S—C28—H28C109.5
C14—C13—Br2120.0 (4)H28A—C28—H28C109.5
C12—C13—Br2118.3 (4)H28B—C28—H28C109.5
C13—C14—C15118.8 (4)C18—N1—C8111.0 (3)
C13—C14—H14120.6C18—N1—H1124.5
C15—C14—H14120.6C8—N1—H1124.5
C14—C15—C10121.0 (4)C20—N2—C21108.9 (3)
C14—C15—H15119.5C20—N2—H2125.6
C10—C15—H15119.5C21—N2—H2125.6
C18—C16—C9109.0 (3)O2—S—C28104.7 (3)
C18—C16—C17124.5 (4)O2—S—C27105.9 (2)
C9—C16—C17126.2 (4)C28—S—C2799.0 (3)
N3—C17—C16178.3 (5)
C6—C1—C2—C30.6 (7)C8—C9—C16—C17171.9 (4)
C1—C2—C3—C43.0 (7)C10—C9—C16—C176.5 (7)
C1—C2—C3—Cl1176.2 (3)C18—C16—C17—N359 (18)
C2—C3—C4—C52.4 (8)C9—C16—C17—N3114 (18)
Cl1—C3—C4—C5176.7 (4)C9—C16—C18—N12.5 (5)
C3—C4—C5—C60.5 (7)C17—C16—C18—N1171.4 (4)
C2—C1—C6—C52.3 (7)C9—C16—C18—C19175.2 (4)
C2—C1—C6—C7178.3 (4)C17—C16—C18—C1911.0 (7)
C4—C5—C6—C12.8 (7)N1—C18—C19—C20154.1 (4)
C4—C5—C6—C7177.7 (4)C16—C18—C19—C2023.2 (7)
C1—C6—C7—O1140.8 (5)N1—C18—C19—C2227.7 (7)
C5—C6—C7—O138.6 (7)C16—C18—C19—C22155.0 (4)
C1—C6—C7—C840.5 (6)C22—C19—C20—N20.1 (5)
C5—C6—C7—C8140.0 (4)C18—C19—C20—N2178.6 (4)
O1—C7—C8—N123.6 (7)N2—C21—C22—C23179.5 (4)
C6—C7—C8—N1157.8 (4)C26—C21—C22—C231.1 (6)
O1—C7—C8—C9152.9 (5)N2—C21—C22—C191.6 (5)
C6—C7—C8—C925.8 (8)C26—C21—C22—C19177.8 (4)
N1—C8—C9—C160.5 (5)C20—C19—C22—C23179.5 (5)
C7—C8—C9—C16176.2 (5)C18—C19—C22—C231.1 (8)
N1—C8—C9—C10178.9 (4)C20—C19—C22—C211.0 (5)
C7—C8—C9—C102.1 (8)C18—C19—C22—C21177.5 (4)
C8—C9—C10—C1150.7 (6)C21—C22—C23—C240.7 (6)
C16—C9—C10—C11127.4 (5)C19—C22—C23—C24179.2 (5)
C8—C9—C10—C15126.0 (5)C22—C23—C24—C251.4 (7)
C16—C9—C10—C1556.0 (6)C22—C23—C24—Br1177.8 (3)
C15—C10—C11—C122.7 (7)C23—C24—C25—C260.3 (7)
C9—C10—C11—C12174.0 (4)Br1—C24—C25—C26178.9 (4)
C10—C11—C12—C130.1 (7)C24—C25—C26—C211.5 (7)
C11—C12—C13—C142.2 (7)N2—C21—C26—C25178.5 (4)
C11—C12—C13—Br2177.9 (3)C22—C21—C26—C252.2 (7)
C12—C13—C14—C151.8 (7)C16—C18—N1—C82.2 (5)
Br2—C13—C14—C15178.3 (3)C19—C18—N1—C8175.7 (4)
C13—C14—C15—C100.9 (7)C9—C8—N1—C181.1 (5)
C11—C10—C15—C143.1 (7)C7—C8—N1—C18178.4 (4)
C9—C10—C15—C14173.7 (4)C19—C20—N2—C211.1 (5)
C8—C9—C16—C181.8 (5)C26—C21—N2—C20177.6 (4)
C10—C9—C16—C18179.8 (4)C22—C21—N2—C201.7 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O20.862.082.812 (4)143
N2—H2···O2i0.861.962.813 (4)170
Symmetry code: (i) x+5/2, y1/2, z+1/2.
 

Acknowledgements

The authors thank Dr Babu Varghese, SAIF, IIT, Chennai, India, for the data collection.

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