Ethyl 3-(4-meth-oxy-phen-yl)-2-phenyl-3-(4-phenyl-1,2,3-selenadiazol-5-yl)propano-ate.

In the title compound, C(26)H(24)N(2)O(3)Se, the selenadiazole ring is planar [maximum deviation = 0.002 (2) Å]. The dihedral angle between the selenadiazole ring and the attached phenyl ring is 49.00 (13)°. The crystal structure is stabilized by inter-molecular C-H⋯N and C-H⋯π inter-actions.

Related literature

For general background to selenadiazole derivatives, see: El-Bahaie et al. (1990 ▶); El-Kashef et al. (1986 ▶); Kuroda et al. (2001 ▶); Padmavathi et al. (2002 ▶); Plano et al. (2010 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C26H24N2O3Se

M = 491.43

Monoclinic,

a = 11.8187 (4) Å

b = 12.8241 (5) Å

c = 16.1837 (6) Å

β = 105.280 (2)°

V = 2366.16 (15) Å3

Z = 4

Mo Kα radiation

μ = 1.62 mm−1

T = 293 K

0.20 × 0.15 × 0.15 mm

Data collection

Bruker SMART APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.748, T max = 0.785

22954 measured reflections

5918 independent reflections

3015 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.108

S = 0.99

5918 reflections

291 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.28 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/S1600536812028322/bt5929sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812028322/bt5929Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812028322/bt5929Isup3.cml

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

C26H24N2O3Se	F(000) = 1008
Mr = 491.43	Dx = 1.380 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5918 reflections
a = 11.8187 (4) Å	θ = 1.8–28.4°
b = 12.8241 (5) Å	µ = 1.62 mm−1
c = 16.1837 (6) Å	T = 293 K
β = 105.280 (2)°	Block, white crystalline
V = 2366.16 (15) Å3	0.20 × 0.15 × 0.15 mm
Z = 4

Bruker SMART APEXII area-detector diffractometer	5918 independent reflections
Radiation source: fine-focus sealed tube	3015 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.046
ω and φ scans	θmax = 28.4°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −15→15
Tmin = 0.748, Tmax = 0.785	k = −13→17
22954 measured reflections	l = −18→21

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108	H-atom parameters constrained
S = 0.99	w = 1/[σ2(Fo2) + (0.0454P)2 + 0.2327P] where P = (Fo2 + 2Fc2)/3
5918 reflections	(Δ/σ)max = 0.002
291 parameters	Δρmax = 0.24 e Å−3
2 restraints	Δρmin = −0.28 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	0.93252 (18)	0.38149 (19)	0.26921 (14)	0.0573 (6)
C2	0.8634 (2)	0.45552 (18)	0.30523 (15)	0.0600 (6)
C3	0.8805 (3)	0.4614 (2)	0.39336 (18)	0.0801 (8)
H3	0.9360	0.4188	0.4292	0.096*
C4	0.8160 (3)	0.5299 (3)	0.4282 (2)	0.0970 (10)
H4	0.8284	0.5335	0.4873	0.116*
C5	0.7334 (3)	0.5929 (3)	0.3758 (3)	0.1004 (10)
H5	0.6889	0.6381	0.3995	0.120*
C6	0.7164 (3)	0.5894 (2)	0.2896 (2)	0.0874 (8)
H6	0.6607	0.6325	0.2544	0.105*
C7	0.7816 (2)	0.5218 (2)	0.25363 (17)	0.0689 (7)
H7	0.7706	0.5208	0.1946	0.083*
C8	0.89231 (18)	0.31086 (19)	0.20497 (14)	0.0552 (6)
C9	0.76498 (17)	0.28768 (18)	0.15966 (13)	0.0517 (6)
H9	0.7194	0.3502	0.1642	0.062*
C10	0.71970 (17)	0.20024 (19)	0.20511 (13)	0.0506 (6)
C11	0.6465 (2)	0.2215 (2)	0.25734 (16)	0.0621 (6)
H11	0.6253	0.2902	0.2643	0.075*
C12	0.6049 (2)	0.1429 (2)	0.29906 (15)	0.0692 (7)
H12	0.5557	0.1589	0.3337	0.083*
C13	0.63546 (19)	0.0406 (2)	0.28997 (14)	0.0610 (6)
C14	0.7102 (2)	0.0182 (2)	0.23980 (14)	0.0602 (6)
H14	0.7331	−0.0502	0.2341	0.072*
C15	0.75087 (19)	0.0977 (2)	0.19819 (14)	0.0569 (6)
H15	0.8010	0.0818	0.1643	0.068*
C16	0.74743 (19)	0.26514 (18)	0.06321 (14)	0.0532 (6)
H16	0.7854	0.1984	0.0581	0.064*
C17	0.6178 (2)	0.25479 (19)	0.01685 (14)	0.0559 (6)
C18	0.5418 (2)	0.3368 (2)	0.01082 (15)	0.0692 (7)
H18	0.5694	0.4004	0.0358	0.083*
C19	0.4241 (2)	0.3260 (3)	−0.03218 (17)	0.0874 (9)
H19	0.3733	0.3821	−0.0357	0.105*
C20	0.3833 (3)	0.2340 (4)	−0.06894 (19)	0.1056 (13)
H20	0.3046	0.2273	−0.0983	0.127*
C21	0.4568 (3)	0.1517 (3)	−0.0631 (2)	0.1099 (12)
H21	0.4280	0.0882	−0.0876	0.132*
C22	0.5750 (2)	0.1614 (2)	−0.02057 (16)	0.0825 (8)
H22	0.6251	0.1048	−0.0174	0.099*
C23	0.8048 (2)	0.3473 (2)	0.02199 (15)	0.0636 (6)
C24	0.9300 (3)	0.3684 (3)	−0.0716 (2)	0.1186 (13)
H24A	0.8975	0.3616	−0.1330	0.142*
H24B	0.9233	0.4409	−0.0563	0.142*
C25	1.0508 (3)	0.3386 (3)	−0.0492 (3)	0.1373 (15)
H25A	1.0866	0.3579	0.0091	0.206*
H25B	1.0901	0.3734	−0.0863	0.206*
H25C	1.0566	0.2645	−0.0555	0.206*
C26	0.6290 (3)	−0.1371 (3)	0.3307 (2)	0.0979 (10)
H26A	0.6117	−0.1605	0.2723	0.147*
H26B	0.5900	−0.1813	0.3624	0.147*
H26C	0.7121	−0.1399	0.3558	0.147*
N1	1.11262 (17)	0.3127 (2)	0.27663 (15)	0.0825 (7)
N2	1.05298 (17)	0.37906 (18)	0.30570 (13)	0.0737 (6)
O1	0.79677 (18)	0.43897 (17)	0.03213 (13)	0.0920 (6)
O2	0.86503 (16)	0.30345 (16)	−0.02744 (11)	0.0793 (5)
O3	0.58939 (16)	−0.03346 (17)	0.33286 (11)	0.0845 (6)
Se1	1.01611 (2)	0.23384 (2)	0.189123 (19)	0.07749 (14)

	U11	U22	U33	U12	U13	U23
C1	0.0423 (12)	0.0620 (15)	0.0588 (14)	−0.0054 (11)	−0.0022 (10)	0.0037 (12)
C2	0.0525 (13)	0.0566 (15)	0.0631 (15)	−0.0116 (12)	0.0011 (11)	−0.0054 (12)
C3	0.087 (2)	0.074 (2)	0.0717 (19)	−0.0048 (16)	0.0061 (15)	0.0003 (15)
C4	0.124 (3)	0.088 (2)	0.084 (2)	−0.012 (2)	0.037 (2)	−0.0146 (19)
C5	0.099 (2)	0.087 (2)	0.123 (3)	0.002 (2)	0.042 (2)	−0.018 (2)
C6	0.0725 (18)	0.071 (2)	0.109 (2)	0.0075 (16)	0.0075 (17)	−0.0109 (18)
C7	0.0575 (14)	0.0651 (17)	0.0728 (16)	−0.0058 (13)	−0.0024 (12)	−0.0041 (14)
C8	0.0386 (11)	0.0635 (15)	0.0582 (13)	0.0012 (11)	0.0032 (10)	0.0024 (12)
C9	0.0339 (10)	0.0581 (15)	0.0572 (13)	0.0005 (10)	0.0018 (9)	−0.0093 (11)
C10	0.0333 (10)	0.0654 (16)	0.0495 (12)	−0.0019 (10)	0.0046 (9)	−0.0100 (11)
C11	0.0460 (12)	0.0768 (17)	0.0615 (15)	0.0070 (13)	0.0105 (11)	−0.0119 (14)
C12	0.0502 (13)	0.103 (2)	0.0595 (15)	−0.0009 (15)	0.0233 (12)	−0.0128 (15)
C13	0.0465 (13)	0.083 (2)	0.0532 (14)	−0.0084 (13)	0.0119 (11)	−0.0031 (13)
C14	0.0530 (13)	0.0678 (16)	0.0602 (14)	−0.0020 (12)	0.0159 (11)	−0.0057 (13)
C15	0.0463 (12)	0.0696 (17)	0.0577 (14)	−0.0014 (12)	0.0190 (11)	−0.0060 (13)
C16	0.0414 (11)	0.0583 (14)	0.0563 (13)	−0.0021 (11)	0.0065 (10)	−0.0027 (11)
C17	0.0450 (12)	0.0755 (18)	0.0434 (12)	−0.0083 (12)	0.0051 (10)	0.0011 (11)
C18	0.0496 (14)	0.091 (2)	0.0614 (15)	−0.0017 (14)	0.0058 (11)	−0.0004 (14)
C19	0.0488 (15)	0.147 (3)	0.0614 (16)	0.0033 (18)	0.0053 (12)	0.0100 (18)
C20	0.0575 (18)	0.185 (4)	0.0605 (18)	−0.036 (2)	−0.0079 (14)	0.014 (2)
C21	0.091 (2)	0.128 (3)	0.089 (2)	−0.052 (2)	−0.0134 (19)	−0.009 (2)
C22	0.0764 (18)	0.083 (2)	0.0766 (17)	−0.0195 (16)	−0.0004 (15)	−0.0111 (16)
C23	0.0447 (13)	0.079 (2)	0.0600 (15)	−0.0092 (14)	0.0021 (11)	0.0016 (15)
C24	0.080 (2)	0.169 (4)	0.110 (2)	−0.011 (2)	0.0330 (19)	0.049 (2)
C25	0.097 (3)	0.108 (3)	0.229 (5)	−0.029 (2)	0.082 (3)	−0.020 (3)
C26	0.105 (2)	0.098 (3)	0.097 (2)	−0.017 (2)	0.0379 (19)	0.0164 (19)
N1	0.0399 (11)	0.1018 (18)	0.0956 (17)	−0.0025 (12)	0.0000 (11)	0.0053 (14)
N2	0.0448 (11)	0.0841 (16)	0.0790 (14)	−0.0109 (11)	−0.0068 (10)	0.0003 (12)
O1	0.0964 (15)	0.0734 (14)	0.1110 (16)	−0.0179 (12)	0.0357 (12)	0.0019 (12)
O2	0.0643 (11)	0.1052 (14)	0.0741 (11)	−0.0009 (11)	0.0280 (10)	0.0144 (11)
O3	0.0791 (12)	0.1050 (16)	0.0787 (12)	−0.0122 (12)	0.0376 (10)	0.0076 (11)
Se1	0.04128 (15)	0.0978 (3)	0.0883 (2)	0.00942 (14)	0.00818 (13)	−0.00765 (16)

C1—C8	1.366 (3)	C16—C23	1.502 (3)
C1—N2	1.390 (3)	C16—C17	1.524 (3)
C1—C2	1.470 (3)	C16—H16	0.9800
C2—C7	1.388 (3)	C17—C18	1.369 (3)
C2—C3	1.389 (3)	C17—C22	1.377 (3)
C3—C4	1.377 (4)	C18—C19	1.389 (3)
C3—H3	0.9300	C18—H18	0.9300
C4—C5	1.375 (4)	C19—C20	1.351 (5)
C4—H4	0.9300	C19—H19	0.9300
C5—C6	1.357 (4)	C20—C21	1.355 (5)
C5—H5	0.9300	C20—H20	0.9300
C6—C7	1.386 (4)	C21—C22	1.390 (4)
C6—H6	0.9300	C21—H21	0.9300
C7—H7	0.9300	C22—H22	0.9300
C8—C9	1.520 (3)	C23—O1	1.194 (3)
C8—Se1	1.838 (2)	C23—O2	1.328 (3)
C9—C10	1.514 (3)	C24—C25	1.429 (4)
C9—C16	1.547 (3)	C24—O2	1.444 (3)
C9—H9	0.9800	C24—H24A	0.9700
C10—C15	1.378 (3)	C24—H24B	0.9700
C10—C11	1.386 (3)	C25—H25A	0.9600
C11—C12	1.375 (3)	C25—H25B	0.9600
C11—H11	0.9300	C25—H25C	0.9600
C12—C13	1.380 (4)	C26—O3	1.412 (4)
C12—H12	0.9300	C26—H26A	0.9600
C13—O3	1.371 (3)	C26—H26B	0.9600
C13—C14	1.378 (3)	C26—H26C	0.9600
C14—C15	1.377 (3)	N1—N2	1.272 (3)
C14—H14	0.9300	N1—Se1	1.865 (2)
C15—H15	0.9300
C8—C1—N2	114.9 (2)	C23—C16—C9	111.16 (19)
C8—C1—C2	127.72 (19)	C17—C16—C9	111.29 (18)
N2—C1—C2	117.4 (2)	C23—C16—H16	107.8
C7—C2—C3	118.3 (3)	C17—C16—H16	107.8
C7—C2—C1	121.9 (2)	C9—C16—H16	107.8
C3—C2—C1	119.8 (2)	C18—C17—C22	118.6 (2)
C4—C3—C2	120.6 (3)	C18—C17—C16	121.6 (2)
C4—C3—H3	119.7	C22—C17—C16	119.8 (2)
C2—C3—H3	119.7	C17—C18—C19	120.7 (3)
C5—C4—C3	120.1 (3)	C17—C18—H18	119.7
C5—C4—H4	119.9	C19—C18—H18	119.7
C3—C4—H4	119.9	C20—C19—C18	120.1 (3)
C6—C5—C4	120.2 (3)	C20—C19—H19	119.9
C6—C5—H5	119.9	C18—C19—H19	119.9
C4—C5—H5	119.9	C19—C20—C21	120.1 (3)
C5—C6—C7	120.3 (3)	C19—C20—H20	120.0
C5—C6—H6	119.9	C21—C20—H20	120.0
C7—C6—H6	119.9	C20—C21—C22	120.5 (3)
C6—C7—C2	120.4 (3)	C20—C21—H21	119.8
C6—C7—H7	119.8	C22—C21—H21	119.8
C2—C7—H7	119.8	C17—C22—C21	120.0 (3)
C1—C8—C9	126.8 (2)	C17—C22—H22	120.0
C1—C8—Se1	109.41 (16)	C21—C22—H22	120.0
C9—C8—Se1	123.43 (17)	O1—C23—O2	125.1 (2)
C10—C9—C8	110.02 (17)	O1—C23—C16	124.6 (3)
C10—C9—C16	112.41 (17)	O2—C23—C16	110.3 (2)
C8—C9—C16	112.08 (18)	C25—C24—O2	110.2 (3)
C10—C9—H9	107.4	C25—C24—H24A	109.6
C8—C9—H9	107.4	O2—C24—H24A	109.6
C16—C9—H9	107.4	C25—C24—H24B	109.6
C15—C10—C11	117.4 (2)	O2—C24—H24B	109.6
C15—C10—C9	122.1 (2)	H24A—C24—H24B	108.1
C11—C10—C9	120.5 (2)	C24—C25—H25A	109.5
C12—C11—C10	121.1 (2)	C24—C25—H25B	109.5
C12—C11—H11	119.4	H25A—C25—H25B	109.5
C10—C11—H11	119.4	C24—C25—H25C	109.5
C11—C12—C13	120.5 (2)	H25A—C25—H25C	109.5
C11—C12—H12	119.8	H25B—C25—H25C	109.5
C13—C12—H12	119.8	O3—C26—H26A	109.5
O3—C13—C14	123.8 (3)	O3—C26—H26B	109.5
O3—C13—C12	117.1 (2)	H26A—C26—H26B	109.5
C14—C13—C12	119.2 (2)	O3—C26—H26C	109.5
C15—C14—C13	119.6 (2)	H26A—C26—H26C	109.5
C15—C14—H14	120.2	H26B—C26—H26C	109.5
C13—C14—H14	120.2	N2—N1—Se1	110.86 (15)
C14—C15—C10	122.1 (2)	N1—N2—C1	117.6 (2)
C14—C15—H15	118.9	C23—O2—C24	119.5 (3)
C10—C15—H15	118.9	C13—O3—C26	117.4 (2)
C23—C16—C17	110.84 (18)	C8—Se1—N1	87.29 (10)
C8—C1—C2—C7	−51.0 (4)	C9—C10—C15—C14	179.68 (19)
N2—C1—C2—C7	131.4 (2)	C10—C9—C16—C23	−173.75 (19)
C8—C1—C2—C3	129.9 (3)	C8—C9—C16—C23	−49.2 (3)
N2—C1—C2—C3	−47.6 (3)	C10—C9—C16—C17	62.2 (2)
C7—C2—C3—C4	1.3 (4)	C8—C9—C16—C17	−173.29 (19)
C1—C2—C3—C4	−179.6 (2)	C23—C16—C17—C18	−60.5 (3)
C2—C3—C4—C5	0.3 (5)	C9—C16—C17—C18	63.8 (3)
C3—C4—C5—C6	−1.2 (5)	C23—C16—C17—C22	119.2 (3)
C4—C5—C6—C7	0.4 (5)	C9—C16—C17—C22	−116.6 (2)
C5—C6—C7—C2	1.2 (4)	C22—C17—C18—C19	0.0 (4)
C3—C2—C7—C6	−2.1 (4)	C16—C17—C18—C19	179.6 (2)
C1—C2—C7—C6	178.9 (2)	C17—C18—C19—C20	−0.3 (4)
N2—C1—C8—C9	173.3 (2)	C18—C19—C20—C21	0.8 (5)
C2—C1—C8—C9	−4.3 (4)	C19—C20—C21—C22	−1.1 (5)
N2—C1—C8—Se1	0.4 (3)	C18—C17—C22—C21	−0.3 (4)
C2—C1—C8—Se1	−177.27 (19)	C16—C17—C22—C21	−179.9 (3)
C1—C8—C9—C10	−91.0 (3)	C20—C21—C22—C17	0.8 (5)
Se1—C8—C9—C10	81.0 (2)	C17—C16—C23—O1	78.4 (3)
C1—C8—C9—C16	143.1 (2)	C9—C16—C23—O1	−46.0 (3)
Se1—C8—C9—C16	−44.8 (3)	C17—C16—C23—O2	−101.3 (2)
C8—C9—C10—C15	−74.9 (3)	C9—C16—C23—O2	134.35 (19)
C16—C9—C10—C15	50.8 (3)	Se1—N1—N2—C1	−0.1 (3)
C8—C9—C10—C11	103.6 (2)	C8—C1—N2—N1	−0.2 (3)
C16—C9—C10—C11	−130.7 (2)	C2—C1—N2—N1	177.7 (2)
C15—C10—C11—C12	−1.4 (3)	O1—C23—O2—C24	2.0 (4)
C9—C10—C11—C12	−179.9 (2)	C16—C23—O2—C24	−178.4 (2)
C10—C11—C12—C13	0.2 (4)	C25—C24—O2—C23	123.3 (3)
C11—C12—C13—O3	−179.3 (2)	C14—C13—O3—C26	5.4 (3)
C11—C12—C13—C14	1.2 (3)	C12—C13—O3—C26	−174.0 (2)
O3—C13—C14—C15	179.1 (2)	C1—C8—Se1—N1	−0.32 (18)
C12—C13—C14—C15	−1.5 (3)	C9—C8—Se1—N1	−173.5 (2)
C13—C14—C15—C10	0.3 (3)	N2—N1—Se1—C8	0.2 (2)
C11—C10—C15—C14	1.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···N1i	0.93	2.57	3.420 (3)	152
C12—H12···Cg4ii	0.96	2.81	3.673 (3)	154
C24—H24A···Cg3iii	0.96	2.80	3.580 (3)	138

Table 1

Hydrogen-bond geometry (Å, °)

Cg3 and Cg4 are the centroids of the C10–C15 and C17–C22 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14⋯N1i	0.93	2.57	3.420 (3)	152
C12—H12⋯Cg4ii	0.96	2.81	3.673 (3)	154
C24—H24A⋯Cg3iii	0.96	2.80	3.580 (3)	138

Symmetry code: (i) .