5-[(Benzo[d][1,3]dioxol-5-yl)meth­yl]-3-[4-(pyridin-2-yl)phen­yl]-4,5-di­hydro­isoxazole

El-Khatatneh, N.; Vinayaka, A.C.; Chandra; Sadashiva, M.P.; Jeyaseelan, S.; Mahendra, M.

doi:10.1107/S2414314617002784

organic compounds

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ISSN: 2414-3146

Volume 2| Part 2| February 2017| x170278

https://doi.org/10.1107/S2414314617002784

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5-[(Benzo[d][1,3]dioxol-5-yl)methyl]-3-[4-(pyridin-2-yl)phenyl]-4,5-dihydroisoxazole

Nasseem El-Khatatneh,^a A. C. Vinayaka,^b Chandra,^a M. P. Sadashiva,^b S. Jeyaseelan ^c and M. Mahendra ^a ^*

^aDepartment of Studies in Physics, Manasagangotri, University of Mysore, Mysore 570 006, India, ^bDepartment of Studies in Chemistry, Manasagangotri, University of Mysore, Mysore 570 006, India, and ^cDepartment of Physics, St Philomena's College, Mysore, India
^*Correspondence e-mail: mahendra@physics.uni-mysore.ac.in

Edited by S. Parkin, University of Kentucky, USA (Received 13 January 2017; accepted 19 February 2017; online 28 February 2017)

In the molecule of the title compound C₂₂H₁₈N₂O₃, the benzodioxole and dihydroisoxazole rings are bridged via a methylene (CH₂) group. The linkage is disordered over two positions with a occupancy factors of 0.887 (5) and 0.113 (5). The dihydroisoxazole and pyridine rings exhibit syn-clinal and anti-periplanar conformations with respect to the benzodioxole and benzene ring groups, as quantified by the torsion angle values of 70.7 (3) and 157.00 (17)°. Aside from van der Waals contacts, there are no significant intermolecular interactions.

Keywords: crystal structure; isoxazole derivatives; hydrogen bonds.

CCDC reference: 1533548

Structure description

Isoxazolines are heterocyclic compounds bearing nitrogen and oxygen at adjacent positions of five-membered rings. Substituted isoxazolines have demonstrated diverse properties, including their use as anti-bacterial (Shah & Desai, 2007 ), anti-cancer (Kamal et al., 2010 ), anti-inflammatory (Habeeb et al., 2001 ) and antifungal agents (Dighade et al., 2003 ). In addition, isoxazolines produced from cycloaddition reactions of nitrile oxide and alkenes have been used as masked β-amino alcohols and β-hydroxy carbonyl aldolates. With this background and as a part of our continuing study of isoxazole derivatives (Chandra et al., 2013 ), the title compound was synthesized and its crystal structure determined.

In the title compound (Fig. 1), there is a small amount of disorder of the methylene linkage between the benzodioxazole and isoxazoline rings, involving atoms C10 and C11, with refined occupancies of 0.887 (5) and 0.113 (5), respectively, for the major and minor components. The dihydroisoxazole and pyridine rings exhibit syn-clinal and anti-periplanar orientations with respect to the benzodioxole and phenyl rings, as indicated by the torsion angles of 70.7 (3)° (O12—C11—C10—C7) and 157.00 (17)° (C18—C19—C22—N27), respectively. In addition, the benzene ring makes dihedral angles of 17.54 (11) and 24.82 (9)° with the mean planes of the dihydroisoxazole and pyridine rings, respectively.

Figure 1
A view of the molecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at 50° probability. Atoms C10 and C11 are shown for the major disorder component [occupancy = 0.887 (5)]. The minor component atoms have been omitted to enhance clarity.

Aside from van der Waals contacts, there are no significant intermolecular interactions. The packing of the molecules viewed down the a axis is shown in Fig. 2.

Figure 2
A packing diagram viewed parallel to the a axis. H atoms have been omitted for the sake of clarity.

Synthesis and crystallization

A solution of 4-(pyridin-2-yl)benzaldehyde (0.002 mol), hydroxylamine hydrochloride (0.002 mol) and triethylamine (0.0025 mol) in DMF was stirred at room temperature for 6 h. After completion of the reaction (monitored by TLC), crushed ice was added to the reaction mixture and the precipitated solid product (an oxime) was filtered, washed with hexane and dried. N-chlorosuccinimide (0.0015 mol) and triethylamine (0.0015 mol) were added to a solution of the oxime (0.001 mol) and safrole (0.0012 mol) in DMF at 0°C. This reaction mixture was stirred at room temperature for 12 h. After completion of reaction, water was added and the product was extracted with ethyl acetate. The combined organic layers were dried and concentrated under reduced pressure. The crude product was purified using silica gel column chromatography. Recrystallization from absolute ethanol solution by slow evaporation yielded block-shaped single crystals after five days.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 1. The disordered positions of the atoms C10 and C11, located between the benzodioxole and dihydroisoxazole rings, were refined with an occupancy ratio of 0.887 (5):0.113 (5).

Table 1
Experimental details

Crystal data
Chemical formula	C₂₂H₁₈N₂O₃
M_r	358.38
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	17.548 (5), 8.719 (3), 12.237 (4)
β (°)	108.380 (9)
V (Å³)	1776.8 (9)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Bruker MicroStar microfocus rotating anode
No. of measured, independent and observed [I > 2σ(I)] reflections	12236, 3242, 2353
R_int	0.067
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.127, 1.05
No. of reflections	3242
No. of parameters	263
No. of restraints	60
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.16
Computer programs: APEX2 and SAINT (Bruker, 2009 ), SHELXS (Sheldrick, 2008 ), SHELXL2016/6 (Sheldrick, 2015 ), PLATON (Spek, 2009 ) and Mercury (Macrae et al., 2008).

Structural data

CCDC reference: 1533548

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S2414314617002784/pk4012sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617002784/pk4012Isup2.hkl

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS (Sheldrick, 2008); program(s) used to refine structure: SHELXL2016/6 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2016/6 (Sheldrick, 2015) and PLATON (Spek, 2009).

5-[(Benzo[d][1,3]dioxol-5-yl)methyl]-3-[4-(pyridin-2-yl)phenyl]-4,5-dihydroisoxazole top

Crystal data top

C₂₂H₁₈N₂O₃	F(000) = 752
M_r = 358.38	D_x = 1.340 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 17.548 (5) Å	Cell parameters from 3242 reflections
b = 8.719 (3) Å	θ = 2.5–25.4°
c = 12.237 (4) Å	µ = 0.09 mm⁻¹
β = 108.380 (9)°	T = 293 K
V = 1776.8 (9) Å³	Block, colourless
Z = 4	0.30 × 0.25 × 0.20 mm

Data collection top

Bruker MicroStar microfocus rotating anode diffractometer	R_int = 0.067
φ and ω scans	θ_max = 25.4°, θ_min = 2.5°
12236 measured reflections	h = −21→19
3242 independent reflections	k = −10→10
2353 reflections with I > 2σ(I)	l = −14→14

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.127	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0725P)²] where P = (F_o² + 2F_c²)/3
3242 reflections	(Δ/σ)_max < 0.001
263 parameters	Δρ_max = 0.15 e Å⁻³
60 restraints	Δρ_min = −0.16 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	Occ. (<1)
C1	0.47963 (13)	0.9248 (3)	0.34808 (19)	0.0910 (7)
H1A	0.476464	1.030174	0.321532	0.109*
H1B	0.532351	0.908313	0.403500	0.109*
O2	0.41886 (8)	0.89620 (18)	0.40031 (11)	0.0904 (5)
C3	0.36100 (10)	0.8108 (2)	0.31934 (14)	0.0573 (5)
C4	0.39006 (10)	0.7669 (2)	0.23254 (15)	0.0590 (5)
O5	0.46718 (7)	0.82244 (18)	0.25346 (12)	0.0840 (5)
C6	0.28619 (10)	0.7700 (2)	0.32070 (14)	0.0599 (5)
H6	0.267161	0.801304	0.379978	0.072*
C8	0.26959 (11)	0.6370 (2)	0.14350 (15)	0.0639 (5)
H8	0.237722	0.577815	0.083071	0.077*
C9	0.34576 (11)	0.6787 (2)	0.14300 (15)	0.0705 (6)
H9	0.365640	0.647985	0.084423	0.085*
C7	0.23922 (10)	0.67991 (18)	0.23030 (14)	0.0516 (4)	0.887 (5)
C10	0.15409 (14)	0.6325 (3)	0.2197 (2)	0.0547 (6)	0.887 (5)
H10A	0.117542	0.692128	0.158454	0.066*	0.887 (5)
H10B	0.147334	0.525643	0.196520	0.066*	0.887 (5)
C11	0.12945 (13)	0.6508 (2)	0.3270 (2)	0.0424 (6)	0.887 (5)
H11	0.170276	0.604578	0.392771	0.051*	0.887 (5)
O12	0.12162 (6)	0.81353 (11)	0.34924 (10)	0.0531 (3)	0.887 (5)
C15	0.04667 (9)	0.58461 (17)	0.31803 (14)	0.0499 (4)	0.887 (5)
H15A	0.013153	0.573540	0.238529	0.060*	0.887 (5)
H15B	0.051054	0.486500	0.356906	0.060*	0.887 (5)
C7'	0.23922 (10)	0.67991 (18)	0.23030 (14)	0.0516 (4)	0.113 (5)
C10'	0.1723 (11)	0.582 (2)	0.276 (2)	0.054 (3)	0.113 (5)
H10C	0.157134	0.487997	0.232027	0.065*	0.113 (5)
H10D	0.196003	0.554748	0.356613	0.065*	0.113 (5)
C11'	0.1014 (11)	0.6773 (18)	0.2615 (18)	0.047 (3)	0.113 (5)
H11'	0.074237	0.708414	0.181713	0.057*	0.113 (5)
O12'	0.12162 (6)	0.81353 (11)	0.34924 (10)	0.0531 (3)	0.113 (5)
C15'	0.04667 (9)	0.58461 (17)	0.31803 (14)	0.0499 (4)	0.113 (5)
H15C	0.003058	0.534073	0.260051	0.060*	0.113 (5)
H15D	0.077513	0.508525	0.371765	0.060*	0.113 (5)
N13	0.05736 (8)	0.83097 (14)	0.39460 (12)	0.0506 (4)
C14	0.01581 (9)	0.70717 (15)	0.37897 (12)	0.0398 (4)
C16	−0.05616 (8)	0.69760 (15)	0.41597 (12)	0.0393 (4)
C17	−0.07063 (9)	0.80733 (16)	0.49036 (13)	0.0455 (4)
H17	−0.033776	0.886052	0.517743	0.055*
C18	−0.13835 (9)	0.80089 (16)	0.52372 (13)	0.0473 (4)
H18	−0.146039	0.874131	0.574493	0.057*
C19	−0.19610 (9)	0.68566 (16)	0.48246 (12)	0.0426 (4)
C20	−0.18195 (9)	0.57667 (17)	0.40750 (12)	0.0465 (4)
H20	−0.219542	0.499587	0.378580	0.056*
C21	−0.11317 (9)	0.58109 (16)	0.37545 (12)	0.0447 (4)
H21	−0.104622	0.506083	0.326543	0.054*
C22	−0.26850 (10)	0.67674 (18)	0.52005 (14)	0.0498 (4)
C23	−0.27040 (12)	0.7388 (2)	0.62257 (17)	0.0738 (6)
H23	−0.225885	0.791438	0.669142	0.089*
C24	−0.33721 (13)	0.7237 (3)	0.6566 (2)	0.0890 (7)
H24	−0.338453	0.765019	0.726104	0.107*
C25	−0.40116 (14)	0.6478 (3)	0.5874 (2)	0.0954 (8)
H25	−0.447397	0.635161	0.608123	0.114*
C26	−0.39649 (14)	0.5894 (3)	0.4855 (2)	0.1125 (10)
H26	−0.440903	0.537175	0.438327	0.135*
N27	−0.33213 (10)	0.6029 (2)	0.44961 (15)	0.0849 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0725 (13)	0.1224 (19)	0.0919 (15)	−0.0282 (13)	0.0456 (12)	−0.0187 (14)
O2	0.0684 (8)	0.1366 (13)	0.0756 (9)	−0.0439 (9)	0.0362 (7)	−0.0360 (9)
C3	0.0549 (10)	0.0713 (12)	0.0488 (10)	−0.0075 (9)	0.0207 (8)	−0.0040 (8)
C4	0.0497 (10)	0.0810 (12)	0.0518 (10)	0.0025 (9)	0.0240 (8)	0.0077 (9)
O5	0.0583 (8)	0.1301 (13)	0.0742 (9)	−0.0154 (8)	0.0360 (7)	−0.0085 (9)
C6	0.0603 (11)	0.0757 (12)	0.0526 (10)	−0.0100 (9)	0.0306 (8)	−0.0120 (9)
C8	0.0614 (11)	0.0793 (13)	0.0529 (10)	−0.0003 (9)	0.0208 (8)	−0.0142 (9)
C9	0.0661 (12)	0.1025 (16)	0.0512 (11)	0.0064 (11)	0.0302 (9)	−0.0079 (10)
C7	0.0536 (10)	0.0527 (10)	0.0513 (9)	−0.0013 (8)	0.0205 (8)	−0.0056 (8)
C10	0.0606 (14)	0.0617 (15)	0.0455 (14)	−0.0097 (11)	0.0218 (11)	−0.0101 (11)
C11	0.0484 (12)	0.0368 (9)	0.0434 (14)	−0.0023 (8)	0.0162 (10)	0.0014 (8)
O12	0.0586 (7)	0.0405 (6)	0.0691 (8)	−0.0076 (5)	0.0328 (6)	−0.0050 (5)
C15	0.0565 (10)	0.0413 (9)	0.0570 (10)	−0.0056 (7)	0.0253 (8)	−0.0051 (7)
C7'	0.0536 (10)	0.0527 (10)	0.0513 (9)	−0.0013 (8)	0.0205 (8)	−0.0056 (8)
C10'	0.059 (6)	0.050 (7)	0.053 (8)	−0.010 (5)	0.016 (6)	0.000 (6)
C11'	0.056 (6)	0.043 (6)	0.039 (7)	−0.016 (5)	0.011 (6)	−0.001 (5)
O12'	0.0586 (7)	0.0405 (6)	0.0691 (8)	−0.0076 (5)	0.0328 (6)	−0.0050 (5)
C15'	0.0565 (10)	0.0413 (9)	0.0570 (10)	−0.0056 (7)	0.0253 (8)	−0.0051 (7)
N13	0.0569 (8)	0.0387 (7)	0.0624 (9)	−0.0057 (6)	0.0277 (7)	−0.0041 (6)
C14	0.0465 (8)	0.0329 (8)	0.0381 (8)	0.0003 (7)	0.0104 (6)	0.0028 (6)
C16	0.0448 (9)	0.0329 (8)	0.0390 (8)	0.0012 (6)	0.0115 (6)	0.0028 (6)
C17	0.0516 (9)	0.0338 (8)	0.0511 (9)	−0.0049 (7)	0.0162 (7)	−0.0038 (7)
C18	0.0572 (10)	0.0365 (8)	0.0505 (9)	0.0013 (7)	0.0203 (8)	−0.0060 (7)
C19	0.0454 (9)	0.0402 (8)	0.0412 (8)	0.0008 (7)	0.0121 (7)	0.0031 (6)
C20	0.0506 (9)	0.0427 (9)	0.0454 (8)	−0.0109 (7)	0.0142 (7)	−0.0064 (7)
C21	0.0546 (9)	0.0372 (8)	0.0435 (8)	−0.0044 (7)	0.0173 (7)	−0.0079 (7)
C22	0.0502 (9)	0.0494 (9)	0.0510 (9)	−0.0015 (8)	0.0177 (8)	−0.0018 (7)
C23	0.0637 (12)	0.0994 (15)	0.0632 (12)	−0.0121 (10)	0.0270 (9)	−0.0261 (11)
C24	0.0831 (15)	0.1189 (19)	0.0782 (14)	−0.0061 (14)	0.0442 (12)	−0.0245 (13)
C25	0.0810 (15)	0.1163 (19)	0.1119 (19)	−0.0210 (14)	0.0634 (15)	−0.0224 (15)
C26	0.0797 (15)	0.151 (2)	0.128 (2)	−0.0545 (15)	0.0627 (15)	−0.0619 (18)
N27	0.0682 (11)	0.1091 (14)	0.0893 (12)	−0.0340 (10)	0.0419 (9)	−0.0387 (11)

Geometric parameters (Å, º) top

C1—O5	1.423 (2)	C11'—O12'	1.565 (15)
C1—O2	1.427 (2)	C11'—C15'	1.573 (15)
O2—C3	1.390 (2)	O12'—N13	1.4134 (15)
C3—C6	1.365 (2)	C15'—C14	1.499 (2)
C3—C4	1.370 (2)	N13—C14	1.2827 (18)
C4—C9	1.364 (3)	C14—C16	1.4723 (19)
C4—O5	1.383 (2)	C16—C17	1.398 (2)
C6—C7'	1.395 (2)	C16—C21	1.402 (2)
C6—C7	1.395 (2)	C17—C18	1.374 (2)
C8—C7'	1.382 (2)	C18—C19	1.403 (2)
C8—C7	1.382 (2)	C19—C20	1.396 (2)
C8—C9	1.387 (2)	C19—C22	1.483 (2)
C7—C10	1.516 (2)	C20—C21	1.382 (2)
C10—C11	1.514 (4)	C22—N27	1.341 (2)
C11—O12	1.459 (2)	C22—C23	1.376 (2)
C11—C15	1.535 (2)	C23—C24	1.369 (3)
O12—N13	1.4134 (15)	C24—C25	1.348 (3)
C15—C14	1.499 (2)	C25—C26	1.372 (3)
C7'—C10'	1.686 (18)	C26—N27	1.340 (2)
C10'—C11'	1.46 (3)

O5—C1—O2	108.04 (15)	O12'—C11'—C15'	97.2 (9)
C3—O2—C1	104.80 (13)	N13—O12'—C11'	108.3 (6)
C6—C3—C4	122.10 (17)	C14—C15'—C11'	102.6 (6)
C6—C3—O2	128.30 (15)	C14—N13—O12	109.71 (11)
C4—C3—O2	109.59 (15)	C14—N13—O12'	109.71 (11)
C9—C4—C3	121.55 (16)	N13—C14—C16	120.28 (12)
C9—C4—O5	128.53 (16)	N13—C14—C15'	113.37 (13)
C3—C4—O5	109.91 (17)	C16—C14—C15'	126.32 (12)
C4—O5—C1	105.10 (14)	N13—C14—C15	113.37 (13)
C3—C6—C7'	117.84 (15)	C16—C14—C15	126.32 (12)
C3—C6—C7	117.84 (15)	C17—C16—C21	118.06 (13)
C7'—C8—C9	122.56 (17)	C17—C16—C14	120.73 (12)
C7—C8—C9	122.56 (17)	C21—C16—C14	121.19 (13)
C4—C9—C8	116.77 (16)	C18—C17—C16	121.14 (13)
C8—C7—C6	119.18 (15)	C17—C18—C19	121.10 (14)
C8—C7—C10	117.97 (16)	C20—C19—C18	117.77 (14)
C6—C7—C10	122.78 (15)	C20—C19—C22	121.00 (13)
C11—C10—C7	116.1 (2)	C18—C19—C22	121.20 (13)
O12—C11—C10	109.52 (19)	C21—C20—C19	121.29 (13)
O12—C11—C15	103.67 (13)	C20—C21—C16	120.62 (13)
C10—C11—C15	114.90 (19)	N27—C22—C23	121.34 (16)
N13—O12—C11	108.16 (10)	N27—C22—C19	116.55 (14)
C14—C15—C11	100.29 (13)	C23—C22—C19	122.10 (15)
C8—C7'—C6	119.18 (15)	C24—C23—C22	120.60 (18)
C8—C7'—C10'	126.6 (6)	C25—C24—C23	118.6 (2)
C6—C7'—C10'	108.8 (7)	C24—C25—C26	118.5 (2)
C11'—C10'—C7'	109.0 (16)	N27—C26—C25	124.3 (2)
C10'—C11'—O12'	110.4 (16)	C26—N27—C22	116.64 (17)
C10'—C11'—C15'	105.5 (16)

O5—C1—O2—C3	−15.6 (2)	C10'—C11'—C15'—C14	139.5 (13)
C1—O2—C3—C6	−171.1 (2)	O12'—C11'—C15'—C14	25.9 (11)
C1—O2—C3—C4	9.9 (2)	C11—O12—N13—C14	−13.84 (18)
C6—C3—C4—C9	−0.6 (3)	C11'—O12'—N13—C14	19.5 (9)
O2—C3—C4—C9	178.55 (18)	O12—N13—C14—C16	−178.32 (11)
C6—C3—C4—O5	−179.39 (16)	O12'—N13—C14—C16	−178.32 (11)
O2—C3—C4—O5	−0.3 (2)	O12'—N13—C14—C15'	−0.43 (17)
C9—C4—O5—C1	171.8 (2)	O12—N13—C14—C15	−0.43 (17)
C3—C4—O5—C1	−9.4 (2)	C11'—C15'—C14—N13	−18.2 (9)
O2—C1—O5—C4	15.5 (2)	C11'—C15'—C14—C16	159.6 (8)
C4—C3—C6—C7'	0.5 (3)	C11—C15—C14—N13	13.34 (18)
O2—C3—C6—C7'	−178.47 (18)	C11—C15—C14—C16	−168.92 (15)
C4—C3—C6—C7	0.5 (3)	N13—C14—C16—C17	−14.3 (2)
O2—C3—C6—C7	−178.47 (18)	C15'—C14—C16—C17	168.09 (14)
C3—C4—C9—C8	0.7 (3)	C15—C14—C16—C17	168.09 (14)
O5—C4—C9—C8	179.26 (18)	N13—C14—C16—C21	163.95 (14)
C7'—C8—C9—C4	−0.7 (3)	C15'—C14—C16—C21	−13.6 (2)
C7—C8—C9—C4	−0.7 (3)	C15—C14—C16—C21	−13.6 (2)
C9—C8—C7—C6	0.7 (3)	C21—C16—C17—C18	0.5 (2)
C9—C8—C7—C10	177.9 (2)	C14—C16—C17—C18	178.82 (12)
C3—C6—C7—C8	−0.5 (3)	C16—C17—C18—C19	−1.3 (2)
C3—C6—C7—C10	−177.6 (2)	C17—C18—C19—C20	0.8 (2)
C8—C7—C10—C11	167.2 (2)	C17—C18—C19—C22	178.84 (13)
C6—C7—C10—C11	−15.8 (3)	C18—C19—C20—C21	0.4 (2)
C7—C10—C11—O12	70.7 (3)	C22—C19—C20—C21	−177.61 (13)
C7—C10—C11—C15	−173.16 (15)	C19—C20—C21—C16	−1.2 (2)
C10—C11—O12—N13	144.47 (18)	C17—C16—C21—C20	0.7 (2)
C15—C11—O12—N13	21.4 (2)	C14—C16—C21—C20	−177.59 (13)
O12—C11—C15—C14	−19.99 (19)	C20—C19—C22—N27	−25.0 (2)
C10—C11—C15—C14	−139.5 (2)	C18—C19—C22—N27	157.00 (17)
C9—C8—C7'—C6	0.7 (3)	C20—C19—C22—C23	154.08 (17)
C9—C8—C7'—C10'	−150.2 (10)	C18—C19—C22—C23	−23.9 (2)
C3—C6—C7'—C8	−0.5 (3)	N27—C22—C23—C24	1.4 (3)
C3—C6—C7'—C10'	155.2 (8)	C19—C22—C23—C24	−177.63 (18)
C8—C7'—C10'—C11'	−120.6 (13)	C22—C23—C24—C25	−0.4 (4)
C6—C7'—C10'—C11'	86.1 (16)	C23—C24—C25—C26	−0.3 (4)
C7'—C10'—C11'—O12'	−70 (2)	C24—C25—C26—N27	0.0 (4)
C7'—C10'—C11'—C15'	−174.2 (9)	C25—C26—N27—C22	1.0 (4)
C10'—C11'—O12'—N13	−137.7 (14)	C23—C22—N27—C26	−1.6 (3)
C15'—C11'—O12'—N13	−28.1 (12)	C19—C22—N27—C26	177.46 (18)

Acknowledgements

MM thanks UGC, New Delhi, Government of India, for awarding a project under the title F. No. 41–920/2012(SR) dated: 25–07–2012.

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