(E)-3-Methyl-2,6-di­phenyl­piperidin-4-one O-(3-methyl­benzo­yl)oxime

Kathiravan, V.; Krishnan, K.G.; Mohandas, T.; Thanikachalam, V.; Sakthivel, P.

doi:10.1107/S1600536814016638

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 70| Part 8| August 2014| Page o883

doi:10.1107/S1600536814016638

Open

access

(E)-3-Methyl-2,6-diphenylpiperidin-4-one O-(3-methylbenzoyl)oxime

V. Kathiravan,^a K. Gokula Krishnan,^b T. Mohandas,^c V. Thanikachalam ^b and P. Sakthivel ^d ^*

^aDepartment of Physics, Goverment Arts College, Karur 639 005, India, ^bDepartment of Chemistry, Annamalai University, Annamalainagar, Chidambaram, India, ^cDepartment of Physics, Shri Angalamman College of Engineering and Technology, Siruganoor, Tiruchirappalli, India, and ^dDepartment of Physics, Urumu Dhanalakshmi College, Tiruchirappalli 620 019, India
^*Correspondence e-mail: sakthi2udc@gmail.com

Edited by M. Bolte, Goethe-Universität Frankfurt, Germany (Received 5 June 2014; accepted 17 July 2014; online 31 July 2014)

In the title compound, C₂₆H₂₆N₂O₂, the piperidine ring exhibits a chair conformation. The phenyl rings are attached to the central heterocycle in an equatorial position. The dihedral angle between the planes of the phenyl rings is 57.58 (8)°. In the crystal, C—H⋯O interactions connect the molecules into zigzag chains along [001].

Keywords: crystal structure; piperidinone; oxime; hydrogen bonding.

CCDC reference: 1005453

Related literature

For the biological activity of oxime esters, see: Crichlow et al. (2007 ); Hwu et al. (2008 ); Neely et al. (2013 ); Liu et al. (2011 ). For ring conformations, see: Cremer & Pople (1975 ). For comparable structures, see: Park et al. (2012a ,b ).

Experimental

Crystal data

C₂₆H₂₆N₂O₂
M_r = 398.49
Monoclinic, P 2₁ /n
a = 10.6265 (6) Å
b = 12.7146 (7) Å
c = 16.4031 (8) Å
β = 99.524 (2)°
V = 2185.7 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.977, T_max = 0.985
37978 measured reflections
5367 independent reflections
3097 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.175
S = 1.04
5367 reflections
275 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O2ⁱ	0.93	2.59	3.485 (3)	160
Symmetry code: (i) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

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 ) and Mercury (Macrae et al., 2008 ); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009 ).

Supporting information

CCDC reference: 1005453

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536814016638/bt6984sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814016638/bt6984Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814016638/bt6984Isup3.cml

checkCIF report

Comment top

The chemistry of oxime esters are serving as important synthetic intermediate, and have been employed as starting materials for both synthetic and medicinal chemistry (Crichlow et al. 2007; Hwu et al.2008; Neely et al.2013). Oxime esters have received great potential in biologically active molecules such as agrochemical industries (Liu et al., 2011).

The central ring (N1/C7/C8/C9/C10/C11) adopts a chair conformation with the puckering parameters Q=0.5398 Å, θ=8.88° and ϕ=30.1509° (Cremer & Pople, 1975).

The bond distances and bond angles in the title compound agree very well with the corresponding values reported in closely related compounds (Park et al., 2012a,b).

This stucture was stabilized by C—H···O intramolecular interactions linking the molecules to zigzag chains running parallel to [001] axis.

Related literature top

For the biological activity of oxime esters. see Crichlow et al. (2007); Hwu et al. (2008) and Neely et al. (2013); Liu et al. (2011). For ring conformations see: Cremer & Pople(1975). For comparable structures, see: Park et al. (2012a, 2012b).

Experimental top

A mixture of 3-methyl-2,6-diphenylpiperidin-4-one oxime (0.73 g, 2.5 mmol) and m-methylbenzoic acid (0.37 g, 2.75 mmol) in dry pyridine (7 ml) was stirred at ambient temperature. POCl₃ (0.25 ml, 2.75 mmol) was added drop wise to the reaction mixture and stirring is continued for 20 to 30 min. The progress of the reaction was monitored by TLC. After completion of the reaction, a saturated solution of NaHCO3 was added portion wise to the reaction mixture and the crude product was thrown out as a precipitate. The crude product was then recrystallized from absolute ethanol to get the pure 3-methyl-2,6-diphenylpiperidin-4-one-O-(3-methylbenzoyl) oxime. Yield 0.76 g (78%).

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) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound with the atom numbering scheme, displacement ellipsoids are drawn at 30% probability level. H atoms are present as small spheres of arbitary radius.
	Fig. 2. Part of crystal structure of the title compound, showing the formation one dimensional C(12) chains running parallel to [0 0 1] axis.

(E)-3-Methyl-2,6-diphenylpiperidin-4-one O-(3-methylbenzoyl)oxime top

Crystal data top

C₂₆H₂₆N₂O₂	F(000) = 848
M_r = 398.49	D_x = 1.211 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3910 reflections
a = 10.6265 (6) Å	θ = 2.0–28.3°
b = 12.7146 (7) Å	µ = 0.08 mm⁻¹
c = 16.4031 (8) Å	T = 293 K
β = 99.524 (2)°	Block, colourless
V = 2185.7 (2) Å³	0.30 × 0.25 × 0.20 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	5367 independent reflections
Radiation source: fine-focus sealed tube	3097 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
ω & ϕ scans	θ_max = 28.3°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −14→14
T_min = 0.977, T_max = 0.985	k = −16→16
37978 measured reflections	l = −21→19

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.175	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.070P)² + 0.8065P] where P = (F_o² + 2F_c²)/3
5367 reflections	(Δ/σ)_max < 0.001
275 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₂₆H₂₆N₂O₂	V = 2185.7 (2) Å³
M_r = 398.49	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.6265 (6) Å	µ = 0.08 mm⁻¹
b = 12.7146 (7) Å	T = 293 K
c = 16.4031 (8) Å	0.30 × 0.25 × 0.20 mm
β = 99.524 (2)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	5367 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	3097 reflections with I > 2σ(I)
T_min = 0.977, T_max = 0.985	R_int = 0.034
37978 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.175	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.25 e Å⁻³
5367 reflections	Δρ_min = −0.23 e Å⁻³
275 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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
H1A	0.018 (2)	1.0450 (18)	0.1578 (13)	0.061 (7)*
O1	0.02902 (16)	0.61978 (10)	0.21324 (9)	0.0619 (4)
O2	−0.06469 (18)	0.49464 (12)	0.27901 (11)	0.0731 (5)
N1	0.04764 (16)	0.99163 (12)	0.18907 (10)	0.0436 (4)
C11	−0.04007 (18)	0.97408 (14)	0.24813 (11)	0.0440 (4)
H11	−0.1257	0.9608	0.2172	0.053*
N2	−0.01386 (18)	0.69687 (13)	0.26740 (11)	0.0564 (5)
C20	0.05405 (18)	0.44768 (15)	0.17305 (12)	0.0456 (4)
C10	0.0019 (2)	0.87831 (15)	0.30293 (12)	0.0515 (5)
H10	0.0828	0.8974	0.3378	0.062*
C7	0.05728 (18)	0.90311 (15)	0.13409 (11)	0.0446 (4)
H7	−0.0282	0.8857	0.1047	0.054*
C6	0.14265 (18)	0.92717 (15)	0.07160 (11)	0.0459 (5)
C9	0.0297 (2)	0.78632 (15)	0.25099 (12)	0.0480 (5)
C12	−0.04334 (19)	1.07383 (15)	0.29832 (11)	0.0445 (4)
C19	−0.00232 (19)	0.51999 (15)	0.22822 (12)	0.0478 (5)
C25	0.10773 (19)	0.48317 (16)	0.10675 (12)	0.0500 (5)
H25	0.1056	0.5547	0.0946	0.060*
C24	0.1646 (2)	0.41475 (18)	0.05806 (13)	0.0563 (5)
C13	−0.1543 (2)	1.13041 (16)	0.29641 (12)	0.0511 (5)
H13	−0.2295	1.1070	0.2643	0.061*
C8	0.1099 (2)	0.80955 (16)	0.18605 (14)	0.0562 (5)
H8A	0.1115	0.7485	0.1508	0.067*
H8B	0.1968	0.8243	0.2123	0.067*
C14	−0.1543 (3)	1.22239 (18)	0.34226 (15)	0.0652 (6)
H14	−0.2294	1.2607	0.3400	0.078*
C15	−0.0451 (3)	1.25700 (18)	0.39050 (15)	0.0694 (7)
H15	−0.0463	1.3177	0.4219	0.083*
C17	0.0669 (2)	1.11168 (17)	0.34612 (14)	0.0606 (6)
H17	0.1433	1.0756	0.3471	0.073*
C16	0.0654 (3)	1.20238 (19)	0.39244 (15)	0.0703 (7)
H16	0.1400	1.2261	0.4250	0.084*
C1	0.2413 (2)	0.99896 (18)	0.08749 (15)	0.0611 (6)
H1	0.2542	1.0365	0.1368	0.073*
C18	−0.0920 (3)	0.85368 (19)	0.36119 (16)	0.0790 (8)
H18A	−0.1044	0.9153	0.3928	0.119*
H18B	−0.0587	0.7979	0.3979	0.119*
H18C	−0.1721	0.8324	0.3295	0.119*
C22	0.1156 (3)	0.27329 (18)	0.14423 (17)	0.0735 (7)
H22	0.1193	0.2019	0.1569	0.088*
C21	0.0567 (2)	0.34152 (16)	0.19135 (15)	0.0590 (6)
H21	0.0192	0.3164	0.2349	0.071*
C23	0.1689 (2)	0.30943 (19)	0.07893 (16)	0.0698 (7)
H23	0.2086	0.2622	0.0481	0.084*
C5	0.1289 (2)	0.87079 (19)	−0.00125 (13)	0.0608 (6)
H5	0.0640	0.8213	−0.0126	0.073*
C4	0.2102 (3)	0.8869 (2)	−0.05753 (14)	0.0768 (8)
H4	0.1998	0.8479	−0.1062	0.092*
C2	0.3212 (3)	1.0150 (2)	0.0298 (2)	0.0838 (8)
H2	0.3864	1.0644	0.0405	0.101*
C3	0.3058 (3)	0.9595 (3)	−0.04244 (18)	0.0880 (9)
H3	0.3597	0.9711	−0.0808	0.106*
C26	0.2245 (3)	0.4555 (3)	−0.01269 (15)	0.0841 (8)
H26A	0.2596	0.3978	−0.0393	0.126*
H26B	0.2912	0.5043	0.0079	0.126*
H26C	0.1609	0.4904	−0.0518	0.126*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0913 (11)	0.0369 (7)	0.0691 (9)	−0.0054 (7)	0.0472 (8)	−0.0056 (7)
O2	0.0998 (13)	0.0492 (9)	0.0847 (11)	0.0049 (8)	0.0569 (10)	0.0115 (8)
N1	0.0528 (10)	0.0380 (8)	0.0433 (9)	0.0039 (7)	0.0178 (7)	0.0007 (7)
C11	0.0469 (11)	0.0431 (10)	0.0446 (10)	−0.0001 (8)	0.0154 (8)	−0.0039 (8)
N2	0.0797 (12)	0.0400 (9)	0.0575 (10)	0.0013 (8)	0.0349 (9)	−0.0037 (8)
C20	0.0474 (11)	0.0413 (10)	0.0487 (11)	−0.0028 (8)	0.0102 (9)	−0.0016 (8)
C10	0.0714 (14)	0.0422 (10)	0.0452 (11)	0.0007 (9)	0.0221 (10)	0.0006 (8)
C7	0.0484 (11)	0.0440 (10)	0.0445 (10)	−0.0022 (8)	0.0166 (8)	−0.0035 (8)
C6	0.0493 (11)	0.0487 (11)	0.0420 (10)	0.0070 (9)	0.0145 (8)	0.0073 (8)
C9	0.0611 (12)	0.0387 (10)	0.0486 (11)	0.0028 (9)	0.0217 (9)	0.0021 (8)
C12	0.0528 (11)	0.0408 (10)	0.0429 (10)	0.0008 (8)	0.0169 (9)	−0.0015 (8)
C19	0.0561 (12)	0.0395 (10)	0.0508 (11)	0.0021 (9)	0.0177 (9)	0.0052 (8)
C25	0.0560 (12)	0.0471 (11)	0.0486 (11)	−0.0020 (9)	0.0136 (9)	−0.0011 (9)
C24	0.0520 (12)	0.0665 (14)	0.0519 (12)	−0.0056 (10)	0.0131 (9)	−0.0136 (10)
C13	0.0547 (12)	0.0510 (12)	0.0519 (11)	0.0030 (9)	0.0214 (9)	0.0016 (9)
C8	0.0706 (14)	0.0422 (11)	0.0638 (13)	0.0050 (10)	0.0350 (11)	0.0044 (9)
C14	0.0804 (17)	0.0522 (13)	0.0720 (15)	0.0162 (12)	0.0390 (13)	0.0023 (11)
C15	0.106 (2)	0.0467 (12)	0.0627 (14)	−0.0041 (13)	0.0359 (14)	−0.0135 (11)
C17	0.0611 (14)	0.0520 (12)	0.0677 (14)	0.0033 (10)	0.0084 (11)	−0.0089 (10)
C16	0.0871 (18)	0.0604 (14)	0.0627 (14)	−0.0126 (13)	0.0103 (13)	−0.0135 (11)
C1	0.0604 (14)	0.0604 (13)	0.0679 (14)	−0.0016 (11)	0.0267 (11)	0.0030 (11)
C18	0.127 (2)	0.0534 (14)	0.0716 (16)	0.0007 (14)	0.0616 (16)	0.0000 (11)
C22	0.0898 (18)	0.0391 (12)	0.0947 (19)	−0.0051 (12)	0.0247 (15)	−0.0114 (12)
C21	0.0699 (14)	0.0406 (11)	0.0693 (14)	−0.0073 (10)	0.0192 (11)	−0.0018 (10)
C23	0.0723 (15)	0.0579 (14)	0.0811 (17)	−0.0024 (12)	0.0180 (13)	−0.0283 (12)
C5	0.0667 (14)	0.0741 (15)	0.0440 (11)	0.0095 (11)	0.0158 (10)	−0.0007 (10)
C4	0.0833 (18)	0.108 (2)	0.0433 (12)	0.0332 (17)	0.0227 (12)	0.0103 (13)
C2	0.0679 (16)	0.0896 (19)	0.103 (2)	−0.0024 (14)	0.0420 (15)	0.0255 (17)
C3	0.085 (2)	0.117 (2)	0.0742 (18)	0.0317 (18)	0.0482 (15)	0.0371 (17)
C26	0.0888 (19)	0.110 (2)	0.0610 (15)	0.0015 (16)	0.0345 (14)	−0.0119 (14)

Geometric parameters (Å, º) top

O1—C19	1.345 (2)	C8—H8A	0.9700
O1—N2	1.446 (2)	C8—H8B	0.9700
O2—C19	1.192 (2)	C14—C15	1.364 (4)
N1—C7	1.456 (2)	C14—H14	0.9300
N1—C11	1.468 (2)	C15—C16	1.360 (4)
N1—H1A	0.88 (2)	C15—H15	0.9300
C11—C12	1.516 (2)	C17—C16	1.383 (3)
C11—C10	1.535 (3)	C17—H17	0.9300
C11—H11	0.9800	C16—H16	0.9300
N2—C9	1.273 (2)	C1—C2	1.387 (3)
C20—C21	1.382 (3)	C1—H1	0.9300
C20—C25	1.384 (3)	C18—H18A	0.9600
C20—C19	1.484 (3)	C18—H18B	0.9600
C10—C9	1.505 (3)	C18—H18C	0.9600
C10—C18	1.524 (3)	C22—C23	1.371 (3)
C10—H10	0.9800	C22—C21	1.379 (3)
C7—C6	1.508 (2)	C22—H22	0.9300
C7—C8	1.516 (3)	C21—H21	0.9300
C7—H7	0.9800	C23—H23	0.9300
C6—C5	1.380 (3)	C5—C4	1.380 (3)
C6—C1	1.382 (3)	C5—H5	0.9300
C9—C8	1.500 (3)	C4—C3	1.365 (4)
C12—C13	1.377 (3)	C4—H4	0.9300
C12—C17	1.384 (3)	C2—C3	1.366 (4)
C25—C24	1.386 (3)	C2—H2	0.9300
C25—H25	0.9300	C3—H3	0.9300
C24—C23	1.381 (3)	C26—H26A	0.9600
C24—C26	1.505 (3)	C26—H26B	0.9600
C13—C14	1.390 (3)	C26—H26C	0.9600
C13—H13	0.9300

C19—O1—N2	114.49 (14)	C7—C8—H8B	109.5
C7—N1—C11	114.11 (15)	H8A—C8—H8B	108.1
C7—N1—H1A	106.9 (14)	C15—C14—C13	120.6 (2)
C11—N1—H1A	107.4 (14)	C15—C14—H14	119.7
N1—C11—C12	107.78 (15)	C13—C14—H14	119.7
N1—C11—C10	110.62 (15)	C16—C15—C14	119.8 (2)
C12—C11—C10	112.10 (15)	C16—C15—H15	120.1
N1—C11—H11	108.8	C14—C15—H15	120.1
C12—C11—H11	108.8	C16—C17—C12	121.0 (2)
C10—C11—H11	108.8	C16—C17—H17	119.5
C9—N2—O1	108.23 (15)	C12—C17—H17	119.5
C21—C20—C25	119.53 (19)	C15—C16—C17	120.1 (2)
C21—C20—C19	117.92 (18)	C15—C16—H16	119.9
C25—C20—C19	122.50 (17)	C17—C16—H16	119.9
C9—C10—C18	113.92 (17)	C6—C1—C2	120.0 (2)
C9—C10—C11	110.50 (15)	C6—C1—H1	120.0
C18—C10—C11	111.89 (18)	C2—C1—H1	120.0
C9—C10—H10	106.7	C10—C18—H18A	109.5
C18—C10—H10	106.7	C10—C18—H18B	109.5
C11—C10—H10	106.7	H18A—C18—H18B	109.5
N1—C7—C6	112.08 (16)	C10—C18—H18C	109.5
N1—C7—C8	108.40 (16)	H18A—C18—H18C	109.5
C6—C7—C8	109.50 (15)	H18B—C18—H18C	109.5
N1—C7—H7	108.9	C23—C22—C21	120.8 (2)
C6—C7—H7	108.9	C23—C22—H22	119.6
C8—C7—H7	108.9	C21—C22—H22	119.6
C5—C6—C1	118.31 (19)	C22—C21—C20	119.2 (2)
C5—C6—C7	119.59 (19)	C22—C21—H21	120.4
C1—C6—C7	121.92 (18)	C20—C21—H21	120.4
N2—C9—C8	126.54 (17)	C22—C23—C24	121.2 (2)
N2—C9—C10	117.54 (17)	C22—C23—H23	119.4
C8—C9—C10	115.90 (16)	C24—C23—H23	119.4
C13—C12—C17	118.20 (19)	C4—C5—C6	120.9 (2)
C13—C12—C11	121.42 (18)	C4—C5—H5	119.5
C17—C12—C11	120.36 (18)	C6—C5—H5	119.5
O2—C19—O1	124.49 (18)	C3—C4—C5	120.6 (3)
O2—C19—C20	125.87 (18)	C3—C4—H4	119.7
O1—C19—C20	109.63 (15)	C5—C4—H4	119.7
C20—C25—C24	121.6 (2)	C3—C2—C1	121.1 (3)
C20—C25—H25	119.2	C3—C2—H2	119.4
C24—C25—H25	119.2	C1—C2—H2	119.4
C23—C24—C25	117.7 (2)	C4—C3—C2	119.0 (2)
C23—C24—C26	121.6 (2)	C4—C3—H3	120.5
C25—C24—C26	120.6 (2)	C2—C3—H3	120.5
C12—C13—C14	120.3 (2)	C24—C26—H26A	109.5
C12—C13—H13	119.9	C24—C26—H26B	109.5
C14—C13—H13	119.9	H26A—C26—H26B	109.5
C9—C8—C7	110.72 (16)	C24—C26—H26C	109.5
C9—C8—H8A	109.5	H26A—C26—H26C	109.5
C7—C8—H8A	109.5	H26B—C26—H26C	109.5
C9—C8—H8B	109.5

C7—N1—C11—C12	−177.94 (16)	C19—C20—C25—C24	177.28 (19)
C7—N1—C11—C10	59.2 (2)	C20—C25—C24—C23	−1.5 (3)
C19—O1—N2—C9	175.23 (19)	C20—C25—C24—C26	−178.8 (2)
N1—C11—C10—C9	−48.2 (2)	C17—C12—C13—C14	−0.6 (3)
C12—C11—C10—C9	−168.54 (16)	C11—C12—C13—C14	−179.19 (17)
N1—C11—C10—C18	−176.30 (18)	N2—C9—C8—C7	131.3 (2)
C12—C11—C10—C18	63.4 (2)	C10—C9—C8—C7	−50.5 (3)
C11—N1—C7—C6	176.81 (16)	N1—C7—C8—C9	55.3 (2)
C11—N1—C7—C8	−62.2 (2)	C6—C7—C8—C9	177.81 (17)
N1—C7—C6—C5	−157.34 (18)	C12—C13—C14—C15	−0.9 (3)
C8—C7—C6—C5	82.3 (2)	C13—C14—C15—C16	1.4 (3)
N1—C7—C6—C1	27.6 (3)	C13—C12—C17—C16	1.6 (3)
C8—C7—C6—C1	−92.7 (2)	C11—C12—C17—C16	−179.80 (19)
O1—N2—C9—C8	0.9 (3)	C14—C15—C16—C17	−0.4 (4)
O1—N2—C9—C10	−177.23 (17)	C12—C17—C16—C15	−1.1 (4)
C18—C10—C9—N2	−8.3 (3)	C5—C6—C1—C2	1.9 (3)
C11—C10—C9—N2	−135.2 (2)	C7—C6—C1—C2	177.0 (2)
C18—C10—C9—C8	173.4 (2)	C23—C22—C21—C20	−1.3 (4)
C11—C10—C9—C8	46.4 (3)	C25—C20—C21—C22	1.6 (3)
N1—C11—C12—C13	117.95 (19)	C19—C20—C21—C22	−176.0 (2)
C10—C11—C12—C13	−120.1 (2)	C21—C22—C23—C24	−0.4 (4)
N1—C11—C12—C17	−60.6 (2)	C25—C24—C23—C22	1.7 (4)
C10—C11—C12—C17	61.4 (2)	C26—C24—C23—C22	179.1 (2)
N2—O1—C19—O2	3.1 (3)	C1—C6—C5—C4	−1.1 (3)
N2—O1—C19—C20	−176.11 (16)	C7—C6—C5—C4	−176.3 (2)
C21—C20—C19—O2	−13.2 (3)	C6—C5—C4—C3	−0.3 (4)
C25—C20—C19—O2	169.3 (2)	C6—C1—C2—C3	−1.2 (4)
C21—C20—C19—O1	165.91 (19)	C5—C4—C3—C2	1.0 (4)
C25—C20—C19—O1	−11.5 (3)	C1—C2—C3—C4	−0.3 (4)
C21—C20—C25—C24	−0.1 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O2ⁱ	0.93	2.59	3.485 (3)	160

Symmetry code: (i) x+1/2, −y+3/2, z−1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O2ⁱ	0.93	2.59	3.485 (3)	160.4

Symmetry code: (i) x+1/2, −y+3/2, z−1/2.

Acknowledgements

The authors thank Dr Babu Varghese, Senior Scientific Officer SAIF, IIT Madras, India, for carrying out the data collection.

References

Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Crichlow, G. V., Cheng, K. F., Dabideen, D., Ochani, M., Aljabari, B., Pavlov, V. A., Miller, E. J., Lolis, E. & Al-Abed, Y. (2007). J. Biol. Chem., 282, 23089–23095. Web of Science CrossRef PubMed CAS Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Hwu, J. R., Yang, J. R., Tsay, S. C., Hsu, M. H., Chen, Y. C. & Chou, S. S. P. (2008). Tetrahedron Lett., 49, 3312–3315. Web of Science CrossRef CAS Google Scholar
Liu, X. H., Pan, L., Tan, C. X., Weng, J. Q., Wang, B. L. & Li, Z. M. (2011). Pestic. Biochem. Physiol., pp. 101–143. Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CrossRef CAS IUCr Journals Google Scholar
Neely, J. M. & Rovis, T. (2013). J. Am. Chem. Soc., 135, 66–69. Web of Science CrossRef CAS PubMed Google Scholar
Park, D. H., Ramkumar, V. & Parthiban, P. (2012a). Acta Cryst. E68, o524. Web of Science CSD CrossRef IUCr Journals Google Scholar
Park, D. H., Ramkumar, V. & Parthiban, P. (2012b). Acta Cryst. E68, o525. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar