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

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

doi:10.1107/S1600536813004662

organic compounds

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ISSN: 2056-9890

Volume 69| Part 3| March 2013| Page o430

doi:10.1107/S1600536813004662

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5-[1-(4-Methylphenyl)-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 29 November 2012; accepted 18 February 2013; online 23 February 2013)

In the title compound, C₁₉H₁₉N₃O₂Se, the selenadiazole ring is roughly planar [maximum deviation 0.033 (6) Å]. The attached phenyl ring is twisted away at an angle of 47.5 (1)°. The butyl group is in an extended conformation [C—C—C—C torsion angle = 174.7 (2)°]. In the crystal, C—H⋯O interactions form C(10) chains running aling the c-axis direction.

Related literature

For general background to selenadiazol derivatives, see: 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

C₁₉H₁₉N₃O₂Se
M_r = 400.33
Triclinic, $[P \overline 1]$
a = 8.2088 (5) Å
b = 8.4755 (5) Å
c = 13.7031 (8) Å
α = 80.669 (3)°
β = 81.832 (3)°
γ = 76.681 (3)°
V = 910.00 (9) Å³
Z = 2
Mo Kα radiation
μ = 2.08 mm⁻¹
T = 293 K
0.22 × 0.20 × 0.18 mm

Data collection

Bruker SMART APEX CCD detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.639, T_max = 0.688
16036 measured reflections
4516 independent reflections
3581 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.083
S = 1.04
4516 reflections
226 parameters
H-atom parameters constrained
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C19—H19C⋯O2ⁱ	0.96	2.52	3.414 (3)	155
Symmetry code: (i) x, y+1, z.

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 for Windows (Farrugia, 2012 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813004662/bt6877sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813004662/bt6877Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813004662/bt6877Isup3.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). These 1,2, 3-selenadiazoles are used as the synthetic intermediates in the preparation of many alkynes and other selenium compounds. In addition, 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). Owing to the above said important properties of selenium containing compounds, the crystal structure of the title compound has been carried out.

The ORTEP plot of the molecule is shown in Fig. 1. The attached phenyl ring is twisted away at an angle of 47.5 (1)° with respect to selenadiazol ring. The bond lengths [Se1—N1] 1.882 (2) Å and [Se1—C8] 1.839 (2) Å are comparable with the values reported in the literature (Allen et al., 1987). In nitro group, the bond lengths [N3—O1] 1.205 (3) Å and [N3—O2] 1.218 (3) Å indicate the typical resonance character.

The tolyl group is oriented to the planar nitro group at an angle of 64.4 (1)°. The butyl group is in an extended conformation, which can be seen from the torsion angle value of [C9—C16—C17—C18 ] 174.7 (2)°. The molecular packing is controlled by C—H···O interactions in addition to van der Waals forces (Fig.2).

Related literature top

For general background to selenadiazol derivatives, see: 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 4-nitro-1-phenyl-3-(4-methylphenyl)-hexan-1-one (1 mmol), semicarbazide hydrochloride (2 mmol) and 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-(2-nitro-1-p-tolylbutyl)-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 for Windows (Farrugia, 2012); 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 displacement ellipsoids drawn at 30% probability level.
	Fig. 2. The crystal packing of the molecules viewed down a axis.

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

Crystal data top

C₁₉H₁₉N₃O₂Se	Z = 2
M_r = 400.33	F(000) = 408
Triclinic, P1	D_x = 1.461 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.2088 (5) Å	Cell parameters from 3581 reflections
b = 8.4755 (5) Å	θ = 1.5–28.4°
c = 13.7031 (8) Å	µ = 2.08 mm⁻¹
α = 80.669 (3)°	T = 293 K
β = 81.832 (3)°	Block, colourless
γ = 76.681 (3)°	0.22 × 0.20 × 0.18 mm
V = 910.00 (9) Å³

Data collection top

Bruker SMART APEX CCD detector diffractometer	4516 independent reflections
Radiation source: fine-focus sealed tube	3581 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
ω scans	θ_max = 28.4°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −10→10
T_min = 0.639, T_max = 0.688	k = −11→11
16036 measured reflections	l = −18→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) = 0.083	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0366P)² + 0.2693P] where P = (F_o² + 2F_c²)/3
4516 reflections	(Δ/σ)_max = 0.001
226 parameters	Δρ_max = 0.37 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

C₁₉H₁₉N₃O₂Se	γ = 76.681 (3)°
M_r = 400.33	V = 910.00 (9) Å³
Triclinic, P1	Z = 2
a = 8.2088 (5) Å	Mo Kα radiation
b = 8.4755 (5) Å	µ = 2.08 mm⁻¹
c = 13.7031 (8) Å	T = 293 K
α = 80.669 (3)°	0.22 × 0.20 × 0.18 mm
β = 81.832 (3)°

Data collection top

Bruker SMART APEX CCD detector diffractometer	4516 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	3581 reflections with I > 2σ(I)
T_min = 0.639, T_max = 0.688	R_int = 0.029
16036 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	0 restraints
wR(F²) = 0.083	H-atom parameters constrained
S = 1.04	Δρ_max = 0.37 e Å⁻³
4516 reflections	Δρ_min = −0.35 e Å⁻³
226 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	0.2947 (3)	0.3855 (3)	1.00144 (16)	0.0503 (5)
H1	0.3533	0.4691	0.9817	0.060*
C2	0.1576 (3)	0.4047 (3)	1.07280 (18)	0.0629 (6)
H2	0.1249	0.5011	1.1013	0.075*
C3	0.0694 (3)	0.2834 (3)	1.10192 (18)	0.0652 (6)
H3	−0.0239	0.2983	1.1493	0.078*
C4	0.1185 (3)	0.1394 (3)	1.06127 (16)	0.0556 (5)
H4	0.0591	0.0566	1.0817	0.067*
C5	0.2557 (3)	0.1179 (3)	0.99035 (14)	0.0458 (4)
H5	0.2885	0.0202	0.9633	0.055*
C6	0.3455 (2)	0.2407 (2)	0.95882 (13)	0.0401 (4)
C7	0.4922 (2)	0.2231 (2)	0.88259 (14)	0.0387 (4)
C8	0.5046 (2)	0.1710 (2)	0.79162 (13)	0.0374 (4)
C9	0.3631 (2)	0.1341 (2)	0.74558 (13)	0.0368 (4)
H9	0.2798	0.1065	0.8006	0.044*
C10	0.2765 (2)	0.2886 (2)	0.68336 (13)	0.0355 (4)
C11	0.3452 (2)	0.3521 (2)	0.59131 (14)	0.0435 (4)
H11	0.4483	0.2974	0.5632	0.052*
C12	0.2619 (3)	0.4961 (3)	0.54083 (15)	0.0472 (5)
H12	0.3104	0.5365	0.4791	0.057*
C13	0.1083 (3)	0.5815 (2)	0.57996 (15)	0.0439 (4)
C14	0.0403 (3)	0.5158 (3)	0.67137 (16)	0.0527 (5)
H14	−0.0634	0.5699	0.6993	0.063*
C15	0.1222 (2)	0.3722 (3)	0.72230 (14)	0.0476 (5)
H15	0.0729	0.3311	0.7836	0.057*
C16	0.4238 (2)	−0.0165 (2)	0.69108 (15)	0.0437 (4)
H16	0.5191	−0.0003	0.6415	0.052*
C17	0.4758 (3)	−0.1734 (3)	0.76190 (19)	0.0647 (6)
H17A	0.5717	−0.1646	0.7931	0.078*
H17B	0.3839	−0.1828	0.8140	0.078*
C18	0.5217 (4)	−0.3281 (3)	0.7132 (3)	0.0928 (10)
H18A	0.5515	−0.4209	0.7625	0.139*
H18B	0.6155	−0.3223	0.6632	0.139*
H18C	0.4271	−0.3393	0.6829	0.139*
C19	0.0164 (3)	0.7377 (3)	0.52454 (19)	0.0585 (6)
H19A	−0.0870	0.7788	0.5635	0.088*
H19B	−0.0079	0.7163	0.4621	0.088*
H19C	0.0856	0.8175	0.5128	0.088*
N1	0.7608 (2)	0.2547 (2)	0.83861 (15)	0.0553 (4)
N2	0.6345 (2)	0.2673 (2)	0.90304 (13)	0.0477 (4)
N3	0.2804 (2)	−0.0354 (2)	0.63942 (14)	0.0503 (4)
O1	0.1466 (2)	−0.0390 (2)	0.68800 (15)	0.0737 (5)
O2	0.3084 (2)	−0.0475 (2)	0.55093 (13)	0.0743 (5)
Se1	0.71589 (3)	0.17548 (3)	0.726788 (16)	0.05444 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0530 (11)	0.0487 (12)	0.0547 (12)	−0.0144 (9)	−0.0076 (9)	−0.0163 (9)
C2	0.0634 (14)	0.0657 (15)	0.0626 (14)	−0.0092 (12)	0.0011 (11)	−0.0309 (12)
C3	0.0566 (13)	0.0859 (18)	0.0541 (13)	−0.0153 (13)	0.0065 (11)	−0.0231 (12)
C4	0.0597 (13)	0.0662 (14)	0.0441 (11)	−0.0243 (11)	−0.0021 (10)	−0.0037 (10)
C5	0.0565 (11)	0.0445 (11)	0.0386 (10)	−0.0149 (9)	−0.0050 (9)	−0.0062 (8)
C6	0.0440 (10)	0.0419 (10)	0.0359 (9)	−0.0078 (8)	−0.0108 (8)	−0.0059 (8)
C7	0.0424 (9)	0.0327 (9)	0.0424 (10)	−0.0087 (7)	−0.0101 (8)	−0.0035 (7)
C8	0.0357 (8)	0.0378 (9)	0.0377 (9)	−0.0082 (7)	−0.0039 (7)	−0.0020 (7)
C9	0.0347 (8)	0.0416 (10)	0.0343 (9)	−0.0096 (7)	−0.0024 (7)	−0.0053 (7)
C10	0.0336 (8)	0.0411 (9)	0.0344 (9)	−0.0099 (7)	−0.0045 (7)	−0.0094 (7)
C11	0.0350 (9)	0.0507 (11)	0.0428 (10)	−0.0083 (8)	0.0023 (8)	−0.0071 (8)
C12	0.0475 (11)	0.0520 (12)	0.0425 (10)	−0.0180 (9)	−0.0027 (8)	0.0012 (9)
C13	0.0479 (10)	0.0422 (10)	0.0470 (11)	−0.0117 (8)	−0.0157 (8)	−0.0092 (8)
C14	0.0436 (10)	0.0608 (13)	0.0476 (11)	0.0066 (9)	−0.0041 (9)	−0.0153 (10)
C15	0.0416 (10)	0.0614 (13)	0.0341 (9)	−0.0037 (9)	0.0020 (8)	−0.0061 (9)
C16	0.0406 (9)	0.0429 (10)	0.0498 (11)	−0.0073 (8)	−0.0093 (8)	−0.0110 (8)
C17	0.0781 (17)	0.0461 (12)	0.0714 (16)	−0.0045 (11)	−0.0276 (13)	−0.0080 (11)
C18	0.107 (2)	0.0507 (15)	0.121 (3)	0.0067 (15)	−0.040 (2)	−0.0229 (16)
C19	0.0648 (14)	0.0447 (12)	0.0698 (14)	−0.0094 (10)	−0.0281 (12)	−0.0042 (10)
N1	0.0464 (9)	0.0612 (11)	0.0647 (12)	−0.0214 (8)	−0.0099 (9)	−0.0091 (9)
N2	0.0479 (9)	0.0458 (9)	0.0551 (10)	−0.0156 (7)	−0.0135 (8)	−0.0085 (8)
N3	0.0512 (10)	0.0465 (10)	0.0584 (11)	−0.0126 (8)	−0.0115 (8)	−0.0135 (8)
O1	0.0512 (9)	0.0907 (13)	0.0909 (13)	−0.0282 (9)	−0.0038 (9)	−0.0312 (10)
O2	0.0850 (13)	0.0909 (13)	0.0587 (10)	−0.0269 (10)	−0.0189 (9)	−0.0225 (9)
Se1	0.03995 (12)	0.07233 (17)	0.05185 (14)	−0.01761 (10)	0.00149 (9)	−0.00817 (10)

Geometric parameters (Å, º) top

C1—C2	1.380 (3)	C12—C13	1.384 (3)
C1—C6	1.396 (3)	C12—H12	0.9300
C1—H1	0.9300	C13—C14	1.382 (3)
C2—C3	1.366 (4)	C13—C19	1.508 (3)
C2—H2	0.9300	C14—C15	1.379 (3)
C3—C4	1.376 (3)	C14—H14	0.9300
C3—H3	0.9300	C15—H15	0.9300
C4—C5	1.377 (3)	C16—N3	1.508 (3)
C4—H4	0.9300	C16—C17	1.526 (3)
C5—C6	1.389 (3)	C16—H16	0.9800
C5—H5	0.9300	C17—C18	1.514 (3)
C6—C7	1.475 (3)	C17—H17A	0.9700
C7—C8	1.372 (3)	C17—H17B	0.9700
C7—N2	1.383 (2)	C18—H18A	0.9600
C8—C9	1.511 (2)	C18—H18B	0.9600
C8—Se1	1.8385 (18)	C18—H18C	0.9600
C9—C10	1.526 (2)	C19—H19A	0.9600
C9—C16	1.532 (3)	C19—H19B	0.9600
C9—H9	0.9800	C19—H19C	0.9600
C10—C15	1.382 (2)	N1—N2	1.259 (2)
C10—C11	1.384 (3)	N1—Se1	1.8824 (19)
C11—C12	1.382 (3)	N3—O1	1.205 (2)
C11—H11	0.9300	N3—O2	1.218 (2)

C2—C1—C6	120.1 (2)	C14—C13—C12	117.15 (18)
C2—C1—H1	120.0	C14—C13—C19	121.15 (19)
C6—C1—H1	120.0	C12—C13—C19	121.7 (2)
C3—C2—C1	120.6 (2)	C15—C14—C13	121.71 (18)
C3—C2—H2	119.7	C15—C14—H14	119.1
C1—C2—H2	119.7	C13—C14—H14	119.1
C2—C3—C4	120.1 (2)	C14—C15—C10	120.83 (19)
C2—C3—H3	120.0	C14—C15—H15	119.6
C4—C3—H3	120.0	C10—C15—H15	119.6
C3—C4—C5	120.0 (2)	N3—C16—C17	107.96 (18)
C3—C4—H4	120.0	N3—C16—C9	108.05 (15)
C5—C4—H4	120.0	C17—C16—C9	112.39 (17)
C4—C5—C6	120.69 (19)	N3—C16—H16	109.5
C4—C5—H5	119.7	C17—C16—H16	109.5
C6—C5—H5	119.7	C9—C16—H16	109.5
C5—C6—C1	118.49 (18)	C18—C17—C16	114.6 (2)
C5—C6—C7	122.41 (17)	C18—C17—H17A	108.6
C1—C6—C7	119.10 (18)	C16—C17—H17A	108.6
C8—C7—N2	115.11 (17)	C18—C17—H17B	108.6
C8—C7—C6	127.85 (17)	C16—C17—H17B	108.6
N2—C7—C6	117.02 (16)	H17A—C17—H17B	107.6
C7—C8—C9	126.13 (16)	C17—C18—H18A	109.5
C7—C8—Se1	109.15 (13)	C17—C18—H18B	109.5
C9—C8—Se1	124.37 (13)	H18A—C18—H18B	109.5
C8—C9—C10	109.47 (15)	C17—C18—H18C	109.5
C8—C9—C16	111.39 (14)	H18A—C18—H18C	109.5
C10—C9—C16	115.25 (15)	H18B—C18—H18C	109.5
C8—C9—H9	106.7	C13—C19—H19A	109.5
C10—C9—H9	106.7	C13—C19—H19B	109.5
C16—C9—H9	106.7	H19A—C19—H19B	109.5
C15—C10—C11	118.05 (18)	C13—C19—H19C	109.5
C15—C10—C9	118.02 (16)	H19A—C19—H19C	109.5
C11—C10—C9	123.92 (16)	H19B—C19—H19C	109.5
C12—C11—C10	120.65 (17)	N2—N1—Se1	110.60 (13)
C12—C11—H11	119.7	N1—N2—C7	118.12 (17)
C10—C11—H11	119.7	O1—N3—O2	124.26 (19)
C11—C12—C13	121.60 (19)	O1—N3—C16	118.29 (18)
C11—C12—H12	119.2	O2—N3—C16	117.45 (18)
C13—C12—H12	119.2	C8—Se1—N1	87.01 (8)

C6—C1—C2—C3	−0.5 (4)	C9—C10—C11—C12	−177.63 (18)
C1—C2—C3—C4	1.0 (4)	C10—C11—C12—C13	0.0 (3)
C2—C3—C4—C5	−0.7 (4)	C11—C12—C13—C14	−0.7 (3)
C3—C4—C5—C6	−0.2 (3)	C11—C12—C13—C19	−179.36 (19)
C4—C5—C6—C1	0.7 (3)	C12—C13—C14—C15	0.7 (3)
C4—C5—C6—C7	−179.56 (19)	C19—C13—C14—C15	179.3 (2)
C2—C1—C6—C5	−0.3 (3)	C13—C14—C15—C10	0.1 (3)
C2—C1—C6—C7	179.92 (19)	C11—C10—C15—C14	−0.9 (3)
C5—C6—C7—C8	48.6 (3)	C9—C10—C15—C14	177.67 (19)
C1—C6—C7—C8	−131.6 (2)	C8—C9—C16—N3	−174.74 (15)
C5—C6—C7—N2	−132.97 (19)	C10—C9—C16—N3	−49.2 (2)
C1—C6—C7—N2	46.8 (2)	C8—C9—C16—C17	66.3 (2)
N2—C7—C8—C9	−172.54 (17)	C10—C9—C16—C17	−168.26 (17)
C6—C7—C8—C9	5.9 (3)	N3—C16—C17—C18	55.6 (3)
N2—C7—C8—Se1	0.9 (2)	C9—C16—C17—C18	174.7 (2)
C6—C7—C8—Se1	179.30 (15)	Se1—N1—N2—C7	0.2 (2)
C7—C8—C9—C10	90.5 (2)	C8—C7—N2—N1	−0.7 (3)
Se1—C8—C9—C10	−81.96 (17)	C6—C7—N2—N1	−179.36 (17)
C7—C8—C9—C16	−140.87 (19)	C17—C16—N3—O1	68.7 (2)
Se1—C8—C9—C16	46.7 (2)	C9—C16—N3—O1	−53.1 (2)
C8—C9—C10—C15	−103.79 (19)	C17—C16—N3—O2	−110.7 (2)
C16—C9—C10—C15	129.73 (19)	C9—C16—N3—O2	127.50 (19)
C8—C9—C10—C11	74.6 (2)	C7—C8—Se1—N1	−0.60 (14)
C16—C9—C10—C11	−51.8 (2)	C9—C8—Se1—N1	172.95 (16)
C15—C10—C11—C12	0.8 (3)	N2—N1—Se1—C8	0.23 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19C···O2ⁱ	0.96	2.52	3.414 (3)	155

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

Experimental details

Crystal data
Chemical formula	C₁₉H₁₉N₃O₂Se
M_r	400.33
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.2088 (5), 8.4755 (5), 13.7031 (8)
α, β, γ (°)	80.669 (3), 81.832 (3), 76.681 (3)
V (Å³)	910.00 (9)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.08
Crystal size (mm)	0.22 × 0.20 × 0.18

Data collection
Diffractometer	Bruker SMART APEX CCD detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.639, 0.688
No. of measured, independent and observed [I > 2σ(I)] reflections	16036, 4516, 3581
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.669

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.083, 1.04
No. of reflections	4516
No. of parameters	226
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.35

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), 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
C19—H19C···O2ⁱ	0.96	2.52	3.414 (3)	154.9

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

Acknowledgements

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

References

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