5-[1-(4-Meth­oxy­phen­yl)-2-nitro­but­yl]-4-phenyl-1,2,3-selenadiazole

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

doi:10.1107/S1600536812020752

organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1784

doi:10.1107/S1600536812020752

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5-[1-(4-Methoxyphenyl)-2-nitrobutyl]-4-phenyl-1,2,3-selenadiazole

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

^aCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India, ^bDepartment of Chemistry, Sri Sarada College for Women (Autonomus), Fairlands, Salem 636 016, India, and ^cDepartment of Industrial Chemistry, Alagappa University, Karaikudi 630 003, India
^*Correspondence e-mail: mnpsy2004@yahoo.com

(Received 23 April 2012; accepted 8 May 2012; online 19 May 2012)

In the title compound, C₁₉H₁₉N₃O₃Se, the selenadiazole ring is essentially planar (r.m.s. deviation = 0.001 Å). The heterocyclic ring makes dihedral angles of 50.2 (2) and 76.3 (9)°, respectively, with the methoxyphenyl and phenyl rings.

Related literature

For general background to selenadiazol derivatives, see: Cuvardic (2003 ); El-Bahaie et al. (1990 ); El-Kashef et al. (1986 ); Kuroda et al. (2001 ); Khanna (2005 ); Padmavathi et al. (2002 ); Plano et al. (2010 ); Stadtman (1991 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₉H₁₉N₃O₃Se
M_r = 416.33
Triclinic, $[P \overline 1]$
a = 8.3072 (5) Å
b = 8.5468 (5) Å
c = 13.6969 (9) Å
α = 81.293 (3)°
β = 79.670 (3)°
γ = 78.888 (3)°
V = 931.88 (10) Å³
Z = 2
Mo Kα radiation
μ = 2.04 mm⁻¹
T = 293 K
0.24 × 0.20 × 0.18 mm

Data collection

Bruker SMART APEX CCD detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.607, T_max = 0.693
16582 measured reflections
4605 independent reflections
3605 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.080
S = 1.02
4605 reflections
237 parameters
H-atom parameters constrained
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.39 e Å⁻³

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/S1600536812020752/bt5896sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812020752/bt5896Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812020752/bt5896Isup3.cml

checkCIF report

Comment top

Selenium containing heterocyclic compounds have gained importance due to their diverse biological, medicinal and synthetic applications. Selenadiazoles, having one selenium and two nitrogen atoms in a five membered ring, are the class of organoselenium compounds utilized in the synthesis of semiconductor nanoparticles (Khanna, 2005). These 1,2,3-selenadiazoles are used as the synthetic intermediates in the preparation of many compounds. In addition, 1,2,3-Selenadiazoles possess 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. Selenium is an essential microelement, necessary for normal functioning of human and animal organisms. Its deficiency in food and feed causes a number of diseases. In high concentrations, selenium is toxic for humans, animals and plants(Cuvardic, 2003).

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). Owing to the above said important properties of selenium containing compounds, the crystal structure of the title compound is carried out.

The ORTEP plot of the molecule is shown in Fig.1. The selenadiazole ring is planar and oriented at an angle of 50.2 (2)° with the attached phenyl ring. The sum of the bond angles around N3 atom in the molecule is 360° indicating sp² hybridized state. The bond lengths [Se1—N1] 1.879 (2) Å and [Se1—C8] 1.844 (2) Å are comparable with the values reported in the literature (Allen et al., 1987). The selenadiazole ring system and the methoxyphenyl group are oriented at an angle of 76.3 (1)° with respect to each other. In nitro group, the bond lengths [N3—O1] 1.215 (2) Å and [N3—O2] 1.210 (2) Å indicate the typical resonance character. The packing of the molecules viewed down c-axis is shown in Fig.2.

Related literature top

For general background to selenadiazol derivatives, see: Cuvardic (2003); El-Bahaie et al. (1990); El-Kashef et al. (1986); Kuroda et al. (2001); Khanna (2005); Padmavathi et al. (2002); Plano et al. (2010); Stadtman (1991). For bond-length data, see: Allen et al. (1987).

Experimental top

A mixture of 3-(4-methoxyphenyl)-4-nitro-1-phenylhexan-1-one(1 mmol), semicarbazide hydrochloride(2 mmol) and anhydrous sodium acetate(3 mmol) in ethanol(10 ml) was refluxed for 4 h. 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 1 h. 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 5-(1-(4-methoxyphenyl) -2-nitrobutyl)-4-phenyl-1,2,3-selenadiazole.

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 30% probability level. Hydrogen atoms have been omitted for clarity.
	Fig. 2. The crystal packing of the molecules viewed down c axis.

5-[1-(4-Methoxyphenyl)-2-nitrobutyl]-4-phenyl-1,2,3-selenadiazole top

Crystal data top

C₁₉H₁₉N₃O₃Se	Z = 2
M_r = 416.33	F(000) = 424
Triclinic, P1	D_x = 1.484 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.3072 (5) Å	Cell parameters from 3605 reflections
b = 8.5468 (5) Å	θ = 1.5–28.3°
c = 13.6969 (9) Å	µ = 2.04 mm⁻¹
α = 81.293 (3)°	T = 293 K
β = 79.670 (3)°	Block, colourless
γ = 78.888 (3)°	0.24 × 0.20 × 0.18 mm
V = 931.88 (10) Å³

Data collection top

Bruker SMART APEX CCD detector diffractometer	4605 independent reflections
Radiation source: fine-focus sealed tube	3605 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
ω scans	θ_max = 28.3°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −11→11
T_min = 0.607, T_max = 0.693	k = −11→11
16582 measured reflections	l = −17→18

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.080	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0368P)² + 0.2368P] where P = (F_o² + 2F_c²)/3
4605 reflections	(Δ/σ)_max = 0.021
237 parameters	Δρ_max = 0.42 e Å⁻³
0 restraints	Δρ_min = −0.39 e Å⁻³

Crystal data top

C₁₉H₁₉N₃O₃Se	γ = 78.888 (3)°
M_r = 416.33	V = 931.88 (10) Å³
Triclinic, P1	Z = 2
a = 8.3072 (5) Å	Mo Kα radiation
b = 8.5468 (5) Å	µ = 2.04 mm⁻¹
c = 13.6969 (9) Å	T = 293 K
α = 81.293 (3)°	0.24 × 0.20 × 0.18 mm
β = 79.670 (3)°

Data collection top

Bruker SMART APEX CCD detector diffractometer	4605 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	3605 reflections with I > 2σ(I)
T_min = 0.607, T_max = 0.693	R_int = 0.024
16582 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	0 restraints
wR(F²) = 0.080	H-atom parameters constrained
S = 1.02	Δρ_max = 0.42 e Å⁻³
4605 reflections	Δρ_min = −0.39 e Å⁻³
237 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	0.7080 (3)	0.1143 (2)	−0.00387 (15)	0.0532 (5)
H1	0.6485	0.0305	0.0178	0.064*
C2	0.8475 (3)	0.0937 (3)	−0.07483 (17)	0.0673 (6)
H2	0.8810	−0.0037	−0.1011	0.081*
C3	0.9378 (3)	0.2151 (3)	−0.10723 (17)	0.0697 (6)
H3	1.0337	0.1992	−0.1540	0.084*
C4	0.8857 (3)	0.3608 (3)	−0.07019 (15)	0.0619 (5)
H4	0.9453	0.4442	−0.0930	0.074*
C5	0.7454 (3)	0.3830 (2)	0.00070 (13)	0.0502 (4)
H5	0.7108	0.4816	0.0253	0.060*
C6	0.6551 (2)	0.2590 (2)	0.03568 (12)	0.0427 (4)
C7	0.5064 (2)	0.27772 (19)	0.11255 (13)	0.0420 (4)
C8	0.4926 (2)	0.33050 (19)	0.20352 (13)	0.0414 (4)
C9	0.6313 (2)	0.37263 (19)	0.24707 (12)	0.0403 (4)
H9	0.7190	0.3932	0.1909	0.048*
C10	0.7054 (2)	0.23002 (19)	0.31467 (12)	0.0404 (4)
C11	0.8557 (2)	0.1404 (2)	0.28056 (14)	0.0514 (4)
H11	0.9122	0.1725	0.2180	0.062*
C12	0.9254 (3)	0.0033 (3)	0.33688 (16)	0.0582 (5)
H12	1.0266	−0.0558	0.3118	0.070*
C13	0.8438 (3)	−0.0443 (2)	0.42993 (15)	0.0516 (5)
C14	0.6949 (3)	0.0457 (2)	0.46637 (14)	0.0557 (5)
H14	0.6406	0.0151	0.5299	0.067*
C15	0.6259 (2)	0.1806 (2)	0.40976 (14)	0.0500 (4)
H15	0.5249	0.2395	0.4353	0.060*
C16	0.5739 (2)	0.5295 (2)	0.29509 (14)	0.0461 (4)
H16	0.4754	0.5191	0.3454	0.055*
C17	0.5340 (3)	0.6751 (2)	0.21955 (17)	0.0648 (6)
H17A	0.4426	0.6606	0.1885	0.078*
H17B	0.6296	0.6801	0.1676	0.078*
C18	0.4881 (4)	0.8345 (3)	0.2628 (2)	0.0881 (8)
H18A	0.3973	0.8291	0.3168	0.132*
H18B	0.4559	0.9189	0.2117	0.132*
H18C	0.5821	0.8560	0.2871	0.132*
C19	1.0446 (4)	−0.2802 (3)	0.4575 (2)	0.0879 (9)
H19A	1.0289	−0.3208	0.3989	0.132*
H19B	1.0674	−0.3681	0.5085	0.132*
H19C	1.1362	−0.2227	0.4413	0.132*
N1	0.2397 (2)	0.2408 (2)	0.16056 (14)	0.0591 (4)
N2	0.3652 (2)	0.23047 (18)	0.09389 (13)	0.0521 (4)
N3	0.7123 (2)	0.55482 (18)	0.34525 (13)	0.0539 (4)
O1	0.6804 (2)	0.5740 (2)	0.43322 (12)	0.0790 (5)
O2	0.8482 (2)	0.5549 (2)	0.29537 (14)	0.0783 (5)
O3	0.8996 (2)	−0.17608 (19)	0.49253 (13)	0.0751 (5)
Se1	0.28223 (2)	0.31972 (3)	0.272539 (16)	0.06042 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0558 (11)	0.0459 (10)	0.0621 (11)	−0.0131 (9)	−0.0071 (9)	−0.0166 (8)
C2	0.0680 (14)	0.0640 (13)	0.0723 (14)	−0.0091 (11)	0.0006 (11)	−0.0321 (11)
C3	0.0630 (13)	0.0850 (16)	0.0616 (13)	−0.0177 (12)	0.0069 (10)	−0.0240 (11)
C4	0.0698 (14)	0.0678 (13)	0.0506 (11)	−0.0279 (11)	0.0000 (10)	−0.0061 (9)
C5	0.0643 (12)	0.0443 (9)	0.0439 (9)	−0.0139 (9)	−0.0083 (8)	−0.0061 (7)
C6	0.0469 (10)	0.0421 (9)	0.0420 (9)	−0.0074 (8)	−0.0123 (7)	−0.0075 (7)
C7	0.0456 (9)	0.0330 (8)	0.0498 (9)	−0.0083 (7)	−0.0110 (8)	−0.0059 (7)
C8	0.0410 (9)	0.0364 (8)	0.0463 (9)	−0.0066 (7)	−0.0057 (7)	−0.0048 (7)
C9	0.0416 (9)	0.0411 (8)	0.0390 (8)	−0.0101 (7)	−0.0025 (7)	−0.0083 (7)
C10	0.0412 (9)	0.0425 (9)	0.0402 (8)	−0.0110 (7)	−0.0049 (7)	−0.0104 (7)
C11	0.0456 (10)	0.0617 (11)	0.0437 (9)	−0.0043 (9)	−0.0015 (8)	−0.0088 (8)
C12	0.0499 (11)	0.0595 (12)	0.0630 (12)	0.0062 (9)	−0.0124 (9)	−0.0161 (10)
C13	0.0604 (12)	0.0458 (10)	0.0563 (11)	−0.0158 (9)	−0.0253 (9)	−0.0028 (8)
C14	0.0620 (12)	0.0632 (12)	0.0448 (10)	−0.0249 (10)	−0.0085 (9)	0.0025 (9)
C15	0.0458 (10)	0.0560 (11)	0.0463 (10)	−0.0097 (8)	0.0013 (8)	−0.0091 (8)
C16	0.0446 (10)	0.0443 (9)	0.0524 (10)	−0.0090 (8)	−0.0085 (8)	−0.0119 (8)
C17	0.0813 (16)	0.0468 (11)	0.0701 (14)	−0.0062 (10)	−0.0249 (12)	−0.0093 (10)
C18	0.113 (2)	0.0459 (12)	0.107 (2)	0.0026 (13)	−0.0318 (18)	−0.0174 (12)
C19	0.0873 (19)	0.0537 (13)	0.134 (2)	−0.0043 (13)	−0.0648 (18)	0.0000 (14)
N1	0.0493 (9)	0.0564 (10)	0.0787 (12)	−0.0193 (8)	−0.0129 (9)	−0.0136 (8)
N2	0.0518 (9)	0.0449 (8)	0.0661 (10)	−0.0138 (7)	−0.0157 (8)	−0.0117 (7)
N3	0.0590 (10)	0.0465 (8)	0.0613 (10)	−0.0122 (8)	−0.0142 (8)	−0.0126 (7)
O1	0.0894 (12)	0.0929 (12)	0.0644 (10)	−0.0116 (10)	−0.0205 (9)	−0.0349 (9)
O2	0.0577 (9)	0.0962 (12)	0.0904 (12)	−0.0340 (9)	−0.0057 (9)	−0.0215 (9)
O3	0.0899 (12)	0.0609 (9)	0.0800 (11)	−0.0170 (9)	−0.0390 (9)	0.0097 (8)
Se1	0.04506 (12)	0.07248 (16)	0.06460 (15)	−0.01676 (10)	0.00230 (9)	−0.01524 (10)

Geometric parameters (Å, º) top

C1—C2	1.374 (3)	C12—H12	0.9300
C1—C6	1.387 (2)	C13—O3	1.366 (2)
C1—H1	0.9300	C13—C14	1.378 (3)
C2—C3	1.370 (3)	C14—C15	1.375 (3)
C2—H2	0.9300	C14—H14	0.9300
C3—C4	1.378 (3)	C15—H15	0.9300
C3—H3	0.9300	C16—N3	1.505 (2)
C4—C5	1.379 (3)	C16—C17	1.517 (3)
C4—H4	0.9300	C16—H16	0.9800
C5—C6	1.393 (2)	C17—C18	1.521 (3)
C5—H5	0.9300	C17—H17A	0.9700
C6—C7	1.473 (2)	C17—H17B	0.9700
C7—C8	1.367 (2)	C18—H18A	0.9600
C7—N2	1.388 (2)	C18—H18B	0.9600
C8—C9	1.512 (2)	C18—H18C	0.9600
C8—Se1	1.8438 (17)	C19—O3	1.407 (3)
C9—C10	1.515 (2)	C19—H19A	0.9600
C9—C16	1.538 (2)	C19—H19B	0.9600
C9—H9	0.9800	C19—H19C	0.9600
C10—C11	1.377 (2)	N1—N2	1.255 (2)
C10—C15	1.394 (2)	N1—Se1	1.8792 (18)
C11—C12	1.388 (3)	N3—O2	1.210 (2)
C11—H11	0.9300	N3—O1	1.215 (2)
C12—C13	1.374 (3)

C2—C1—C6	120.59 (18)	O3—C13—C14	115.45 (18)
C2—C1—H1	119.7	C12—C13—C14	119.47 (18)
C6—C1—H1	119.7	C15—C14—C13	120.66 (18)
C3—C2—C1	120.67 (19)	C15—C14—H14	119.7
C3—C2—H2	119.7	C13—C14—H14	119.7
C1—C2—H2	119.7	C14—C15—C10	120.88 (18)
C2—C3—C4	119.7 (2)	C14—C15—H15	119.6
C2—C3—H3	120.2	C10—C15—H15	119.6
C4—C3—H3	120.2	N3—C16—C17	108.37 (15)
C3—C4—C5	120.12 (19)	N3—C16—C9	107.81 (14)
C3—C4—H4	119.9	C17—C16—C9	112.92 (15)
C5—C4—H4	119.9	N3—C16—H16	109.2
C4—C5—C6	120.54 (18)	C17—C16—H16	109.2
C4—C5—H5	119.7	C9—C16—H16	109.2
C6—C5—H5	119.7	C16—C17—C18	114.67 (19)
C1—C6—C5	118.39 (17)	C16—C17—H17A	108.6
C1—C6—C7	119.66 (16)	C18—C17—H17A	108.6
C5—C6—C7	121.95 (15)	C16—C17—H17B	108.6
C8—C7—N2	115.27 (16)	C18—C17—H17B	108.6
C8—C7—C6	127.29 (16)	H17A—C17—H17B	107.6
N2—C7—C6	117.37 (15)	C17—C18—H18A	109.5
C7—C8—C9	126.18 (15)	C17—C18—H18B	109.5
C7—C8—Se1	109.09 (13)	H18A—C18—H18B	109.5
C9—C8—Se1	124.37 (12)	C17—C18—H18C	109.5
C8—C9—C10	110.23 (13)	H18A—C18—H18C	109.5
C8—C9—C16	110.96 (14)	H18B—C18—H18C	109.5
C10—C9—C16	115.08 (14)	O3—C19—H19A	109.5
C8—C9—H9	106.7	O3—C19—H19B	109.5
C10—C9—H9	106.7	H19A—C19—H19B	109.5
C16—C9—H9	106.7	O3—C19—H19C	109.5
C11—C10—C15	117.54 (17)	H19A—C19—H19C	109.5
C11—C10—C9	119.27 (15)	H19B—C19—H19C	109.5
C15—C10—C9	123.16 (16)	N2—N1—Se1	111.05 (12)
C10—C11—C12	121.92 (17)	N1—N2—C7	117.76 (16)
C10—C11—H11	119.0	O2—N3—O1	124.24 (19)
C12—C11—H11	119.0	O2—N3—C16	117.87 (17)
C13—C12—C11	119.51 (18)	O1—N3—C16	117.89 (17)
C13—C12—H12	120.2	C13—O3—C19	118.6 (2)
C11—C12—H12	120.2	C8—Se1—N1	86.83 (7)
O3—C13—C12	125.1 (2)

C6—C1—C2—C3	0.5 (4)	C10—C11—C12—C13	−0.7 (3)
C1—C2—C3—C4	−1.7 (4)	C11—C12—C13—O3	−179.72 (18)
C2—C3—C4—C5	1.4 (4)	C11—C12—C13—C14	−0.7 (3)
C3—C4—C5—C6	0.1 (3)	O3—C13—C14—C15	−179.59 (17)
C2—C1—C6—C5	0.9 (3)	C12—C13—C14—C15	1.3 (3)
C2—C1—C6—C7	−179.2 (2)	C13—C14—C15—C10	−0.5 (3)
C4—C5—C6—C1	−1.2 (3)	C11—C10—C15—C14	−0.9 (3)
C4—C5—C6—C7	178.94 (19)	C9—C10—C15—C14	176.95 (16)
C1—C6—C7—C8	128.2 (2)	C8—C9—C16—N3	174.57 (14)
C5—C6—C7—C8	−52.0 (3)	C10—C9—C16—N3	48.55 (19)
C1—C6—C7—N2	−48.7 (2)	C8—C9—C16—C17	−65.7 (2)
C5—C6—C7—N2	131.17 (18)	C10—C9—C16—C17	168.24 (16)
N2—C7—C8—C9	173.33 (15)	N3—C16—C17—C18	−56.6 (3)
C6—C7—C8—C9	−3.6 (3)	C9—C16—C17—C18	−176.0 (2)
N2—C7—C8—Se1	0.06 (19)	Se1—N1—N2—C7	−0.5 (2)
C6—C7—C8—Se1	−176.86 (14)	C8—C7—N2—N1	0.3 (2)
C7—C8—C9—C10	−95.23 (19)	C6—C7—N2—N1	177.56 (16)
Se1—C8—C9—C10	77.06 (17)	C17—C16—N3—O2	−68.0 (2)
C7—C8—C9—C16	136.09 (17)	C9—C16—N3—O2	54.5 (2)
Se1—C8—C9—C16	−51.62 (19)	C17—C16—N3—O1	112.0 (2)
C8—C9—C10—C11	103.29 (18)	C9—C16—N3—O1	−125.52 (18)
C16—C9—C10—C11	−130.31 (17)	C12—C13—O3—C19	−5.6 (3)
C8—C9—C10—C15	−74.5 (2)	C14—C13—O3—C19	175.42 (18)
C16—C9—C10—C15	51.9 (2)	C7—C8—Se1—N1	−0.26 (13)
C15—C10—C11—C12	1.5 (3)	C9—C8—Se1—N1	−173.68 (15)
C9—C10—C11—C12	−176.43 (17)	N2—N1—Se1—C8	0.44 (14)

Experimental details

Crystal data
Chemical formula	C₁₉H₁₉N₃O₃Se
M_r	416.33
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.3072 (5), 8.5468 (5), 13.6969 (9)
α, β, γ (°)	81.293 (3), 79.670 (3), 78.888 (3)
V (Å³)	931.88 (10)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.04
Crystal size (mm)	0.24 × 0.20 × 0.18

Data collection
Diffractometer	Bruker SMART APEX CCD detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.607, 0.693
No. of measured, independent and observed [I > 2σ(I)] reflections	16582, 4605, 3605
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.080, 1.02
No. of reflections	4605
No. of parameters	237
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.42, −0.39

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

Acknowledgements

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

References

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