Ethyl 2-phenyl-3-(4-phenyl-1,2,3-selenadiazol-5-yl)-3-p-tolyl­propano­ate

Sankari, S.; Sugumar, P.; Manisankar, T.; Muthusubramanian, S.; Ponnuswamy, M.N.

doi:10.1107/S1600536811056017

organic compounds

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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Page o447

doi:10.1107/S1600536811056017

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Ethyl 2-phenyl-3-(4-phenyl-1,2,3-selenadiazol-5-yl)-3-p-tolylpropanoate

S. Sankari,^a P. Sugumar,^b T. Manisankar,^c S. Muthusubramanian ^d and M. N. Ponnuswamy ^b ^*

^aDepartment of Chemistry, Sri Sarada College for Women (Autonomus), Fairlands, Salem-600 016, India, ^bCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India, ^cDepartment of Industrial Chemistry, Alagappa University, Karaikudi 630 003, India, and ^dSchool of Chemistry, Madurai Kamaraj University, Madurai 625 021, India
^*Correspondence e-mail: mnpsy2004@yahoo.com

(Received 12 December 2011; accepted 28 December 2011; online 18 January 2012)

In the title compound, C₂₆H₂₄N₂O₂Se, the selenadiazole ring is essentially planar [maximum deviation = 0.004 (3) Å]. The dihedral angle between the selenadiazole ring and the attached benzene ring is 50.17 (1)°. The crystal packing is stabilized by intermolecular C—H⋯N interactions.

Related literature

For general background to selenadiazol derivatives, see: El-Bahaie et al. (1990 ); El-Kashef et al. (1986 ); Khanna (2005 ); Kuroda et al. (2001 ); Padmavathi et al. (2002 ); Plano et al. (2010 ); Stadtman (1991 ).

Experimental

Crystal data

C₂₆H₂₄N₂O₂Se
M_r = 475.43
Monoclinic, P 2₁ /c
a = 12.148 (5) Å
b = 12.333 (5) Å
c = 16.522 (5) Å
β = 108.768 (5)°
V = 2343.7 (15) Å³
Z = 4
Mo Kα radiation
μ = 1.63 mm⁻¹
T = 293 K
0.20 × 0.20 × 0.15 mm

Data collection

Bruker SMART APEX CCD detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.715, T_max = 0.784
21985 measured reflections
5739 independent reflections
3536 reflections with I > 2σ(I)
R_int = 0.038

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.114
S = 1.02
5739 reflections
282 parameters
H-atom parameters constrained
Δρ_max = 0.63 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C20—H20⋯N1ⁱ	0.93	2.61	3.522 (4)	165
Symmetry code: (i) $[x+1, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811056017/bt5750sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811056017/bt5750Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811056017/bt5750Isup3.cml

checkCIF report

Comment top

Selenadiazoles, having one selenium and two nitrogen atoms in a five membered ring, are the important class of organoselenium compounds utilized in the synthesis of semiconductor nanoparticles (Khanna, 2005). 1,2,3-Selenadiazoles are of interest owing to their chemical properties and biological applications such as anti-fungal (Kuroda et al., 2001), anti-bacterial (El-Kashef et al., 1986), anti-microbial (El-Bahaie et al.,1990), anti-cancer (Plano et al., 2010) and insecticidal (Padmavathi et al., 2002) properties.

Glutathione peroxidases(GPx) are the antioxidant selenoenzymes protecting various organisms from oxidative stress by catalyzing the reduction of hydroperoxides at the expense of glutathione(GSH) (Stadtman, 1991). In view of the above important properties of selenium containing compounds, an attempt is made to determine the crystal structure of the title compound.

The ORTEP plot of the molecule is shown in Fig.1. The selenadiazol ring is planar and oriented at an angle of 50.17 (1)° with the attached phenyl ring. The planar phenyl rings are twisted away across the propanyl bond at an angle of 73.7 (1)°. The propanoate group assumes partially an extended conformation which can seen from the torsion angle value of [C9—C16—C23—O2] 138.0 (2)°. The molecular packing is controlled by C—H···N intermolecular interactions in addition to van der Waals forces.

Related literature top

For general background to selenadiazol derivatives, see: El-Bahaie et al. (1990); El-Kashef et al. (1986); Khanna (2005); Kuroda et al. (2001); Padmavathi et al. (2002); Plano et al. (2010); Stadtman (1991).

Experimental top

A mixture of ethyl-5-oxo-2,5-diphenyl-3-p-tolylpentanoate (1 mmol), semicarbazide hydrochloride(2 mmol) and anhydrous sodium acetate (3 mmol) in ethanol (10 ml) was refluxed for 4 hrs. After completion of the reaction as monitored by TLC, the mixture was poured into ice cold water and the resulting semicarbazone was filtered off. Then, a mixture of semicarbazone (1 mmol) and SeO₂ (2 mmol) in tetrahydrofuran (10 ml) were refluxed on a water bath for 1hr. The selenium deposited on cooling was removed by filtration, and the filtrate was poured into crushed ice, extracted with dichloromethane, and purified by column chromatography using silica gel (60–120 mesh) with 97:3 petroleum ether: ethyl acetate as eluent to give ethyl-2-phenyl-3-(4-phenyl-1,2, 3-selenadiazol-5-yl)-3-p-tolylpropanoate.

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 (Farrugia, 1997); 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, showing the atomic numbering and displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. The packing of the molecules viewed down the b-axis.

Ethyl 2-phenyl-3-(4-phenyl-1,2,3-selenadiazol-5-yl)-3-p-tolylpropanoate top

Crystal data top

C₂₆H₂₄N₂O₂Se	F(000) = 976
M_r = 475.43	D_x = 1.347 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3536 reflections
a = 12.148 (5) Å	θ = 1.8–28.3°
b = 12.333 (5) Å	µ = 1.63 mm⁻¹
c = 16.522 (5) Å	T = 293 K
β = 108.768 (5)°	Block, white crystalline
V = 2343.7 (15) Å³	0.20 × 0.20 × 0.15 mm
Z = 4

Data collection top

Bruker SMART APEX CCD detector diffractometer	5739 independent reflections
Radiation source: fine-focus sealed tube	3536 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
ω scans	θ_max = 28.3°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −16→16
T_min = 0.715, T_max = 0.784	k = −16→15
21985 measured reflections	l = −22→21

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.114	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.045P)² + 0.8234P] where P = (F_o² + 2F_c²)/3
5739 reflections	(Δ/σ)_max = 0.007
282 parameters	Δρ_max = 0.63 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₂₆H₂₄N₂O₂Se	V = 2343.7 (15) Å³
M_r = 475.43	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.148 (5) Å	µ = 1.63 mm⁻¹
b = 12.333 (5) Å	T = 293 K
c = 16.522 (5) Å	0.20 × 0.20 × 0.15 mm
β = 108.768 (5)°

Data collection top

Bruker SMART APEX CCD detector diffractometer	5739 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	3536 reflections with I > 2σ(I)
T_min = 0.715, T_max = 0.784	R_int = 0.038
21985 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.114	H-atom parameters constrained
S = 1.02	Δρ_max = 0.63 e Å⁻³
5739 reflections	Δρ_min = −0.30 e Å⁻³
282 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
C1	0.6317 (3)	0.4864 (2)	0.10829 (19)	0.0747 (8)
H1	0.5772	0.4457	0.0671	0.090*
C2	0.6984 (4)	0.5621 (3)	0.0839 (3)	0.1018 (12)
H2	0.6887	0.5724	0.0263	0.122*
C3	0.7792 (4)	0.6224 (3)	0.1445 (3)	0.1074 (13)
H3	0.8253	0.6723	0.1280	0.129*
C4	0.7917 (3)	0.6089 (3)	0.2288 (3)	0.0909 (11)
H4	0.8454	0.6510	0.2696	0.109*
C5	0.7258 (2)	0.5336 (2)	0.25435 (19)	0.0663 (7)
H5	0.7351	0.5248	0.3121	0.080*
C6	0.6456 (2)	0.47105 (19)	0.19370 (16)	0.0548 (6)
C7	0.57234 (19)	0.3898 (2)	0.21839 (15)	0.0511 (6)
C8	0.60737 (18)	0.3091 (2)	0.27673 (14)	0.0466 (5)
C9	0.73116 (18)	0.27921 (18)	0.32782 (13)	0.0432 (5)
H9	0.7791	0.3442	0.3320	0.052*
C10	0.77602 (18)	0.19359 (19)	0.28023 (13)	0.0444 (5)
C11	0.8454 (2)	0.2243 (2)	0.23223 (16)	0.0542 (6)
H11	0.8655	0.2969	0.2306	0.065*
C12	0.8852 (2)	0.1489 (3)	0.18676 (17)	0.0687 (8)
H12	0.9314	0.1716	0.1547	0.082*
C13	0.8582 (2)	0.0407 (3)	0.18788 (17)	0.0673 (8)
C14	0.7875 (3)	0.0105 (2)	0.23479 (17)	0.0674 (7)
H14	0.7667	−0.0620	0.2356	0.081*
C15	0.7469 (2)	0.0853 (2)	0.28051 (16)	0.0582 (6)
H15	0.6996	0.0626	0.3118	0.070*
C16	0.74223 (19)	0.24382 (19)	0.41975 (14)	0.0470 (5)
H16	0.6991	0.1760	0.4166	0.056*
C17	0.8681 (2)	0.2242 (2)	0.47442 (14)	0.0546 (6)
C18	0.9536 (2)	0.2983 (3)	0.47948 (17)	0.0817 (10)
H18	0.9356	0.3627	0.4488	0.098*
C19	1.0676 (3)	0.2777 (4)	0.5303 (2)	0.1065 (14)
H19	1.1259	0.3280	0.5337	0.128*
C20	1.0928 (3)	0.1821 (4)	0.5755 (2)	0.1085 (14)
H20	1.1690	0.1669	0.6085	0.130*
C21	1.0084 (4)	0.1112 (4)	0.5723 (3)	0.1197 (15)
H21	1.0255	0.0481	0.6047	0.144*
C22	0.8967 (3)	0.1310 (3)	0.5213 (2)	0.0866 (10)
H22	0.8391	0.0801	0.5185	0.104*
C23	0.6893 (2)	0.3282 (3)	0.46202 (15)	0.0548 (6)
C24	0.5688 (3)	0.3495 (3)	0.5502 (2)	0.0914 (10)
H24A	0.5929	0.3296	0.6102	0.110*
H24B	0.5898	0.4247	0.5462	0.110*
C25	0.4454 (3)	0.3374 (3)	0.5139 (3)	0.1169 (14)
H25A	0.4205	0.3645	0.4564	0.175*
H25B	0.4078	0.3775	0.5473	0.175*
H25C	0.4253	0.2621	0.5136	0.175*
C26	0.9020 (3)	−0.0422 (3)	0.1379 (2)	0.1073 (13)
H26A	0.8593	−0.0354	0.0781	0.161*
H26B	0.8915	−0.1137	0.1571	0.161*
H26C	0.9831	−0.0299	0.1468	0.161*
N1	0.39102 (19)	0.3233 (3)	0.19430 (17)	0.0838 (8)
N2	0.45350 (19)	0.3936 (2)	0.17484 (14)	0.0701 (6)
O1	0.70126 (18)	0.42406 (18)	0.45645 (13)	0.0752 (5)
O2	0.62809 (16)	0.28144 (16)	0.50584 (12)	0.0692 (5)
Se1	0.48065 (2)	0.22922 (3)	0.27871 (2)	0.07445 (14)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.090 (2)	0.0605 (18)	0.0701 (18)	0.0122 (16)	0.0208 (16)	0.0119 (14)
C2	0.136 (3)	0.083 (3)	0.098 (3)	0.019 (2)	0.053 (3)	0.029 (2)
C3	0.104 (3)	0.076 (3)	0.154 (4)	0.002 (2)	0.058 (3)	0.035 (3)
C4	0.071 (2)	0.059 (2)	0.131 (3)	−0.0017 (16)	0.017 (2)	0.007 (2)
C5	0.0551 (15)	0.0573 (17)	0.0774 (18)	0.0087 (13)	0.0085 (13)	0.0041 (14)
C6	0.0513 (13)	0.0466 (14)	0.0608 (15)	0.0148 (11)	0.0102 (11)	0.0049 (11)
C7	0.0396 (12)	0.0551 (15)	0.0512 (13)	0.0097 (10)	0.0045 (10)	−0.0050 (11)
C8	0.0366 (11)	0.0546 (14)	0.0452 (12)	0.0022 (10)	0.0083 (9)	−0.0033 (10)
C9	0.0352 (10)	0.0473 (13)	0.0442 (11)	0.0011 (9)	0.0085 (9)	0.0041 (10)
C10	0.0367 (11)	0.0522 (14)	0.0411 (11)	0.0048 (9)	0.0080 (9)	0.0061 (10)
C11	0.0448 (12)	0.0603 (15)	0.0583 (14)	0.0015 (11)	0.0176 (11)	0.0031 (12)
C12	0.0526 (15)	0.095 (2)	0.0645 (16)	0.0135 (15)	0.0268 (13)	0.0031 (15)
C13	0.0634 (16)	0.077 (2)	0.0576 (15)	0.0270 (15)	0.0138 (13)	0.0000 (14)
C14	0.0788 (18)	0.0554 (16)	0.0640 (16)	0.0120 (14)	0.0173 (15)	0.0007 (13)
C15	0.0626 (15)	0.0572 (16)	0.0564 (14)	0.0028 (12)	0.0215 (12)	0.0063 (12)
C16	0.0399 (11)	0.0549 (14)	0.0461 (12)	0.0030 (10)	0.0138 (9)	0.0046 (10)
C17	0.0457 (13)	0.0763 (17)	0.0405 (12)	0.0120 (12)	0.0120 (10)	0.0049 (12)
C18	0.0463 (15)	0.137 (3)	0.0567 (16)	−0.0064 (17)	0.0095 (12)	0.0272 (17)
C19	0.0470 (16)	0.210 (5)	0.0564 (18)	−0.013 (2)	0.0074 (14)	0.015 (2)
C20	0.060 (2)	0.183 (4)	0.066 (2)	0.043 (3)	−0.0019 (17)	−0.008 (3)
C21	0.101 (3)	0.109 (3)	0.108 (3)	0.041 (3)	−0.025 (2)	0.008 (2)
C22	0.078 (2)	0.075 (2)	0.083 (2)	0.0132 (17)	−0.0055 (16)	0.0092 (17)
C23	0.0440 (12)	0.0723 (19)	0.0446 (13)	0.0063 (12)	0.0093 (10)	0.0031 (12)
C24	0.076 (2)	0.126 (3)	0.085 (2)	0.001 (2)	0.0431 (17)	−0.025 (2)
C25	0.075 (2)	0.109 (3)	0.176 (4)	0.009 (2)	0.053 (3)	−0.033 (3)
C26	0.113 (3)	0.110 (3)	0.104 (3)	0.050 (2)	0.042 (2)	−0.015 (2)
N1	0.0359 (11)	0.112 (2)	0.0921 (18)	0.0028 (13)	0.0046 (12)	−0.0034 (16)
N2	0.0437 (12)	0.0825 (17)	0.0696 (14)	0.0147 (12)	−0.0020 (10)	0.0015 (12)
O1	0.0862 (14)	0.0675 (14)	0.0794 (13)	0.0092 (11)	0.0371 (11)	−0.0021 (10)
O2	0.0616 (11)	0.0898 (14)	0.0664 (11)	−0.0013 (10)	0.0349 (9)	−0.0087 (10)
Se1	0.04194 (15)	0.0938 (3)	0.0834 (2)	−0.01152 (14)	0.01441 (13)	0.00719 (16)

Geometric parameters (Å, º) top

C1—C2	1.379 (5)	C15—H15	0.9300
C1—C6	1.379 (4)	C16—C23	1.508 (4)
C1—H1	0.9300	C16—C17	1.525 (3)
C2—C3	1.373 (6)	C16—H16	0.9800
C2—H2	0.9300	C17—C18	1.365 (4)
C3—C4	1.361 (5)	C17—C22	1.367 (4)
C3—H3	0.9300	C18—C19	1.392 (4)
C4—C5	1.379 (4)	C18—H18	0.9300
C4—H4	0.9300	C19—C20	1.376 (6)
C5—C6	1.385 (4)	C19—H19	0.9300
C5—H5	0.9300	C20—C21	1.336 (6)
C6—C7	1.482 (4)	C20—H20	0.9300
C7—C8	1.355 (3)	C21—C22	1.369 (5)
C7—N2	1.391 (3)	C21—H21	0.9300
C8—C9	1.514 (3)	C22—H22	0.9300
C8—Se1	1.837 (2)	C23—O1	1.198 (3)
C9—C10	1.518 (3)	C23—O2	1.325 (3)
C9—C16	1.544 (3)	C24—C25	1.432 (5)
C9—H9	0.9800	C24—O2	1.449 (3)
C10—C15	1.383 (3)	C24—H24A	0.9700
C10—C11	1.383 (3)	C24—H24B	0.9700
C11—C12	1.377 (4)	C25—H25A	0.9600
C11—H11	0.9300	C25—H25B	0.9600
C12—C13	1.376 (4)	C25—H25C	0.9600
C12—H12	0.9300	C26—H26A	0.9600
C13—C14	1.381 (4)	C26—H26B	0.9600
C13—C26	1.514 (4)	C26—H26C	0.9600
C14—C15	1.380 (4)	N1—N2	1.261 (3)
C14—H14	0.9300	N1—Se1	1.870 (3)

C2—C1—C6	120.1 (3)	C23—C16—C9	110.20 (19)
C2—C1—H1	119.9	C17—C16—C9	112.39 (18)
C6—C1—H1	119.9	C23—C16—H16	108.3
C3—C2—C1	120.2 (4)	C17—C16—H16	108.3
C3—C2—H2	119.9	C9—C16—H16	108.3
C1—C2—H2	119.9	C18—C17—C22	118.6 (3)
C4—C3—C2	119.9 (4)	C18—C17—C16	121.9 (2)
C4—C3—H3	120.0	C22—C17—C16	119.5 (2)
C2—C3—H3	120.0	C17—C18—C19	120.3 (3)
C3—C4—C5	120.7 (3)	C17—C18—H18	119.9
C3—C4—H4	119.7	C19—C18—H18	119.9
C5—C4—H4	119.7	C20—C19—C18	119.2 (4)
C4—C5—C6	119.7 (3)	C20—C19—H19	120.4
C4—C5—H5	120.1	C18—C19—H19	120.4
C6—C5—H5	120.1	C21—C20—C19	120.3 (3)
C1—C6—C5	119.3 (3)	C21—C20—H20	119.8
C1—C6—C7	119.2 (2)	C19—C20—H20	119.8
C5—C6—C7	121.5 (2)	C20—C21—C22	120.3 (4)
C8—C7—N2	115.4 (2)	C20—C21—H21	119.9
C8—C7—C6	127.8 (2)	C22—C21—H21	119.9
N2—C7—C6	116.7 (2)	C17—C22—C21	121.3 (4)
C7—C8—C9	127.1 (2)	C17—C22—H22	119.4
C7—C8—Se1	109.47 (16)	C21—C22—H22	119.4
C9—C8—Se1	123.15 (17)	O1—C23—O2	125.1 (2)
C8—C9—C10	109.78 (17)	O1—C23—C16	124.4 (2)
C8—C9—C16	111.95 (18)	O2—C23—C16	110.5 (2)
C10—C9—C16	112.37 (18)	C25—C24—O2	110.6 (3)
C8—C9—H9	107.5	C25—C24—H24A	109.5
C10—C9—H9	107.5	O2—C24—H24A	109.5
C16—C9—H9	107.5	C25—C24—H24B	109.5
C15—C10—C11	118.0 (2)	O2—C24—H24B	109.5
C15—C10—C9	122.4 (2)	H24A—C24—H24B	108.1
C11—C10—C9	119.5 (2)	C24—C25—H25A	109.5
C12—C11—C10	120.9 (3)	C24—C25—H25B	109.5
C12—C11—H11	119.5	H25A—C25—H25B	109.5
C10—C11—H11	119.5	C24—C25—H25C	109.5
C13—C12—C11	121.3 (3)	H25A—C25—H25C	109.5
C13—C12—H12	119.3	H25B—C25—H25C	109.5
C11—C12—H12	119.3	C13—C26—H26A	109.5
C12—C13—C14	117.7 (3)	C13—C26—H26B	109.5
C12—C13—C26	121.3 (3)	H26A—C26—H26B	109.5
C14—C13—C26	121.0 (3)	C13—C26—H26C	109.5
C15—C14—C13	121.5 (3)	H26A—C26—H26C	109.5
C15—C14—H14	119.2	H26B—C26—H26C	109.5
C13—C14—H14	119.2	N2—N1—Se1	111.30 (17)
C14—C15—C10	120.5 (2)	N1—N2—C7	117.0 (2)
C14—C15—H15	119.7	C23—O2—C24	118.8 (2)
C10—C15—H15	119.7	C8—Se1—N1	86.80 (11)
C23—C16—C17	109.34 (19)

C6—C1—C2—C3	0.1 (5)	C11—C10—C15—C14	0.7 (3)
C1—C2—C3—C4	−1.4 (6)	C9—C10—C15—C14	178.5 (2)
C2—C3—C4—C5	1.4 (6)	C8—C9—C16—C23	−52.2 (3)
C3—C4—C5—C6	−0.2 (5)	C10—C9—C16—C23	−176.23 (19)
C2—C1—C6—C5	1.1 (4)	C8—C9—C16—C17	−174.4 (2)
C2—C1—C6—C7	179.6 (3)	C10—C9—C16—C17	61.6 (3)
C4—C5—C6—C1	−1.0 (4)	C23—C16—C17—C18	−72.9 (3)
C4—C5—C6—C7	−179.5 (2)	C9—C16—C17—C18	49.8 (3)
C1—C6—C7—C8	129.3 (3)	C23—C16—C17—C22	105.8 (3)
C5—C6—C7—C8	−52.2 (4)	C9—C16—C17—C22	−131.5 (3)
C1—C6—C7—N2	−48.3 (3)	C22—C17—C18—C19	1.1 (4)
C5—C6—C7—N2	130.1 (2)	C16—C17—C18—C19	179.8 (3)
N2—C7—C8—C9	174.4 (2)	C17—C18—C19—C20	−0.2 (5)
C6—C7—C8—C9	−3.3 (4)	C18—C19—C20—C21	−1.6 (6)
N2—C7—C8—Se1	−0.1 (3)	C19—C20—C21—C22	2.5 (7)
C6—C7—C8—Se1	−177.8 (2)	C18—C17—C22—C21	−0.2 (5)
C7—C8—C9—C10	−91.6 (3)	C16—C17—C22—C21	−178.9 (3)
Se1—C8—C9—C10	82.2 (2)	C20—C21—C22—C17	−1.6 (6)
C7—C8—C9—C16	142.9 (2)	C17—C16—C23—O1	82.0 (3)
Se1—C8—C9—C16	−43.3 (3)	C9—C16—C23—O1	−42.0 (3)
C8—C9—C10—C15	−78.9 (3)	C17—C16—C23—O2	−98.0 (2)
C16—C9—C10—C15	46.4 (3)	C9—C16—C23—O2	138.0 (2)
C8—C9—C10—C11	98.8 (2)	Se1—N1—N2—C7	−0.7 (3)
C16—C9—C10—C11	−135.9 (2)	C8—C7—N2—N1	0.6 (3)
C15—C10—C11—C12	−0.6 (3)	C6—C7—N2—N1	178.5 (2)
C9—C10—C11—C12	−178.5 (2)	O1—C23—O2—C24	0.9 (4)
C10—C11—C12—C13	−0.4 (4)	C16—C23—O2—C24	−179.1 (2)
C11—C12—C13—C14	1.4 (4)	C25—C24—O2—C23	114.7 (3)
C11—C12—C13—C26	−180.0 (3)	C7—C8—Se1—N1	−0.20 (19)
C12—C13—C14—C15	−1.3 (4)	C9—C8—Se1—N1	−175.0 (2)
C26—C13—C14—C15	−180.0 (3)	N2—N1—Se1—C8	0.5 (2)
C13—C14—C15—C10	0.3 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20···N1ⁱ	0.93	2.61	3.522 (4)	165

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

Experimental details

Crystal data
Chemical formula	C₂₆H₂₄N₂O₂Se
M_r	475.43
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	12.148 (5), 12.333 (5), 16.522 (5)
β (°)	108.768 (5)
V (Å³)	2343.7 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.63
Crystal size (mm)	0.20 × 0.20 × 0.15

Data collection
Diffractometer	Bruker SMART APEX CCD detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.715, 0.784
No. of measured, independent and observed [I > 2σ(I)] reflections	21985, 5739, 3536
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.114, 1.02
No. of reflections	5739
No. of parameters	282
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.63, −0.30

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20···N1ⁱ	0.93	2.61	3.522 (4)	165.2

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

Acknowledgements

The authors thank the TBI Consultancy, University of Madras, India, for the data collection.

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