Ethyl 2-phenyl-3-(4-phenyl-1,2,3-selenadiazol-5-yl)-3-p-tolyl-propano-ate.

In the title compound, C(26)H(24)N(2)O(2)Se, 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 inter-molecular C-H⋯N inter-actions.

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 = 475.43

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.114

S = 1.02

5739 reflections

282 parameters

H-atom parameters constrained

Δρmax = 0.63 e Å−3

Δρmin = −0.30 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/S1600536811056017/bt5750sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536811056017/bt5750Isup3.cml

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

C26H24N2O2Se	F(000) = 976
Mr = 475.43	Dx = 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

Bruker SMART APEX CCD detector diffractometer	5739 independent reflections
Radiation source: fine-focus sealed tube	3536 reflections with I > 2σ(I)
graphite	Rint = 0.038
ω scans	θmax = 28.3°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −16→16
Tmin = 0.715, Tmax = 0.784	k = −16→15
21985 measured reflections	l = −22→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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.045P)2 + 0.8234P] where P = (Fo2 + 2Fc2)/3
5739 reflections	(Δ/σ)max = 0.007
282 parameters	Δρmax = 0.63 e Å−3
0 restraints	Δρmin = −0.30 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	0.6317 (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)

	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)

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)

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

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) .