5-[1-(4-Meth-oxy-phen-yl)-2-nitro-but-yl]-4-phenyl-1,2,3-selenadiazole.

In the title compound, C(19)H(19)N(3)O(3)Se, 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 meth-oxy-phenyl 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 = 416.33

Triclinic,

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[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.080

S = 1.02

4605 reflections

237 parameters

H-atom parameters constrained

Δρmax = 0.42 e Å−3

Δρmin = −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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812020752/bt5896sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536812020752/bt5896Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C19H19N3O3Se	Z = 2
Mr = 416.33	F(000) = 424
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.0368P)2 + 0.2368P] where P = (Fo2 + 2Fc2)/3
4605 reflections	(Δ/σ)max = 0.021
237 parameters	Δρmax = 0.42 e Å−3
0 restraints	Δρmin = −0.39 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)