Ethyl 3-(4-chloro-phen-yl)-2-phenyl-3-(4-phenyl-1,2,3-selena-diazol-5-yl)propano-ate.

In the title compound, C25H21ClN2O2Se, the selena-diazole ring is almost planar [maximum deviation = 0.004 (2) Å], and the adjacent benzene ring is twisted by 50.6 (1)° with respect to this ring.

Related literature

For general background to selena­diazol derivatives, see: Khanna (2005 ▶). For related structures, see: Marx et al. (2008 ▶); Muthukumaran et al. (2011 ▶).

Experimental

Crystal data

C25H21ClN2O2Se

M = 495.85

Monoclinic,

a = 12.1337 (3) Å

b = 12.2267 (3) Å

c = 16.4423 (4) Å

β = 107.744 (1)°

V = 2323.26 (10) Å3

Z = 4

Mo Kα radiation

μ = 1.76 mm−1

T = 293 K

0.25 × 0.20 × 0.18 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.663, T max = 0.729

22323 measured reflections

5764 independent reflections

3745 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.107

S = 1.02

5764 reflections

280 parameters

H-atom parameters constrained

Δρmax = 0.42 e Å−3

Δρmin = −0.27 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 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813017790/ng5333sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813017790/ng5333Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813017790/ng5333Isup3.cml

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

C25H21ClN2O2Se	F(000) = 1008
Mr = 495.85	Dx = 1.418 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5764 reflections
a = 12.1337 (3) Å	θ = 1.8–28.4°
b = 12.2267 (3) Å	µ = 1.76 mm−1
c = 16.4423 (4) Å	T = 293 K
β = 107.744 (1)°	Block, yellow
V = 2323.26 (10) Å3	0.25 × 0.20 × 0.18 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	5764 independent reflections
Radiation source: fine-focus sealed tube	3745 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
ω and φ scans	θmax = 28.4°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −12→16
Tmin = 0.663, Tmax = 0.729	k = −16→15
22323 measured reflections	l = −21→19

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0471P)2 + 0.6047P] where P = (Fo2 + 2Fc2)/3
5764 reflections	(Δ/σ)max = 0.002
280 parameters	Δρmax = 0.42 e Å−3
0 restraints	Δρmin = −0.27 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	0.7760 (2)	0.5374 (2)	0.74986 (16)	0.0633 (6)
H1	0.7656	0.5310	0.6916	0.076*
C2	0.7134 (3)	0.6137 (2)	0.7793 (2)	0.0836 (9)
H2	0.6610	0.6588	0.7407	0.100*
C3	0.7278 (3)	0.6234 (3)	0.8652 (3)	0.0954 (10)
H3	0.6847	0.6744	0.8846	0.114*
C4	0.8054 (3)	0.5580 (3)	0.9219 (2)	0.0908 (10)
H4	0.8151	0.5647	0.9800	0.109*
C5	0.8696 (2)	0.4818 (2)	0.89387 (17)	0.0706 (7)
H5	0.9230	0.4381	0.9331	0.085*
C6	0.85467 (19)	0.47046 (18)	0.80734 (14)	0.0536 (5)
C7	0.92554 (18)	0.38995 (18)	0.77867 (13)	0.0502 (5)
C8	0.88943 (17)	0.31106 (18)	0.71769 (13)	0.0469 (5)
C9	0.76586 (16)	0.28344 (17)	0.66740 (12)	0.0428 (4)
H9	0.7191	0.3492	0.6659	0.051*
C10	0.72046 (16)	0.19519 (17)	0.71371 (12)	0.0426 (4)
C11	0.64815 (19)	0.2233 (2)	0.76108 (15)	0.0549 (5)
H11	0.6269	0.2960	0.7634	0.066*
C12	0.6070 (2)	0.1451 (2)	0.80495 (15)	0.0656 (7)
H12	0.5585	0.1648	0.8367	0.079*
C13	0.6383 (2)	0.0383 (2)	0.80109 (15)	0.0631 (7)
C14	0.7116 (2)	0.0082 (2)	0.75615 (15)	0.0622 (6)
H14	0.7338	−0.0644	0.7551	0.075*
C15	0.7521 (2)	0.08659 (19)	0.71257 (14)	0.0538 (5)
H15	0.8016	0.0663	0.6818	0.065*
C16	0.75310 (17)	0.25174 (17)	0.57420 (13)	0.0456 (5)
H16	0.7931	0.1820	0.5747	0.055*
C17	0.62689 (19)	0.23681 (19)	0.52183 (13)	0.0497 (5)
C18	0.5471 (2)	0.3186 (2)	0.51442 (14)	0.0640 (6)
H18	0.5699	0.3853	0.5415	0.077*
C19	0.4325 (2)	0.3023 (3)	0.46674 (16)	0.0834 (9)
H19	0.3785	0.3579	0.4619	0.100*
C20	0.3993 (3)	0.2040 (4)	0.4268 (2)	0.0985 (12)
H20	0.3222	0.1923	0.3958	0.118*
C21	0.4772 (3)	0.1247 (3)	0.4322 (2)	0.1093 (13)
H21	0.4542	0.0589	0.4037	0.131*
C22	0.5919 (3)	0.1399 (2)	0.47981 (18)	0.0818 (8)
H22	0.6454	0.0842	0.4833	0.098*
C23	0.80904 (19)	0.3363 (2)	0.53277 (14)	0.0533 (5)
C24	0.9294 (3)	0.3559 (3)	0.4427 (2)	0.0910 (9)
H24A	0.9033	0.3406	0.3820	0.109*
H24B	0.9149	0.4325	0.4509	0.109*
C25	1.0522 (3)	0.3337 (3)	0.4767 (3)	0.1152 (13)
H25A	1.0935	0.3782	0.4477	0.173*
H25B	1.0663	0.2579	0.4683	0.173*
H25C	1.0781	0.3502	0.5366	0.173*
N1	1.04418 (17)	0.39168 (19)	0.81995 (13)	0.0663 (5)
N2	1.10574 (18)	0.3221 (2)	0.79702 (15)	0.0766 (6)
O1	0.80184 (17)	0.43304 (16)	0.54165 (12)	0.0777 (5)
O2	0.86582 (16)	0.28857 (15)	0.48558 (11)	0.0679 (5)
Cl1	0.58491 (9)	−0.06117 (8)	0.85433 (6)	0.1057 (3)
Se1	1.01461 (2)	0.23132 (3)	0.710678 (17)	0.06928 (12)

	U11	U22	U33	U12	U13	U23
C1	0.0524 (13)	0.0566 (14)	0.0712 (15)	−0.0052 (11)	0.0043 (11)	−0.0039 (12)
C2	0.0652 (17)	0.0621 (17)	0.109 (2)	0.0021 (14)	0.0058 (16)	−0.0044 (16)
C3	0.090 (2)	0.079 (2)	0.120 (3)	0.0026 (18)	0.036 (2)	−0.025 (2)
C4	0.119 (3)	0.079 (2)	0.080 (2)	−0.015 (2)	0.039 (2)	−0.0217 (17)
C5	0.0822 (19)	0.0585 (16)	0.0642 (16)	−0.0078 (13)	0.0121 (13)	−0.0058 (12)
C6	0.0494 (12)	0.0467 (12)	0.0576 (13)	−0.0146 (10)	0.0057 (10)	−0.0040 (10)
C7	0.0385 (11)	0.0530 (13)	0.0515 (12)	−0.0106 (9)	0.0025 (9)	0.0027 (10)
C8	0.0350 (10)	0.0535 (12)	0.0485 (11)	−0.0031 (9)	0.0071 (8)	0.0028 (9)
C9	0.0331 (9)	0.0476 (12)	0.0437 (11)	−0.0031 (8)	0.0056 (8)	−0.0046 (8)
C10	0.0336 (9)	0.0515 (12)	0.0391 (10)	−0.0046 (8)	0.0058 (8)	−0.0060 (8)
C11	0.0436 (11)	0.0644 (14)	0.0559 (13)	0.0018 (10)	0.0142 (10)	−0.0053 (11)
C12	0.0503 (13)	0.093 (2)	0.0591 (14)	−0.0091 (13)	0.0247 (11)	−0.0038 (13)
C13	0.0588 (14)	0.0749 (18)	0.0536 (13)	−0.0249 (13)	0.0141 (11)	0.0025 (12)
C14	0.0702 (16)	0.0545 (14)	0.0609 (14)	−0.0117 (12)	0.0185 (12)	−0.0019 (11)
C15	0.0561 (13)	0.0543 (14)	0.0546 (13)	−0.0043 (10)	0.0222 (10)	−0.0054 (10)
C16	0.0383 (10)	0.0516 (13)	0.0451 (11)	−0.0037 (9)	0.0098 (8)	−0.0024 (9)
C17	0.0447 (11)	0.0649 (14)	0.0365 (10)	−0.0117 (10)	0.0082 (8)	−0.0027 (9)
C18	0.0468 (13)	0.0940 (19)	0.0471 (13)	0.0022 (13)	0.0082 (10)	−0.0126 (12)
C19	0.0429 (13)	0.148 (3)	0.0523 (14)	0.0061 (16)	0.0045 (11)	−0.0008 (16)
C20	0.0558 (18)	0.154 (4)	0.0665 (18)	−0.038 (2)	−0.0093 (14)	0.011 (2)
C21	0.097 (3)	0.095 (3)	0.101 (2)	−0.043 (2)	−0.024 (2)	−0.007 (2)
C22	0.0739 (18)	0.0680 (18)	0.0809 (18)	−0.0149 (14)	−0.0103 (14)	−0.0079 (14)
C23	0.0448 (12)	0.0626 (16)	0.0478 (12)	−0.0083 (10)	0.0073 (9)	0.0007 (10)
C24	0.085 (2)	0.114 (3)	0.086 (2)	−0.0062 (19)	0.0439 (17)	0.0262 (18)
C25	0.087 (3)	0.094 (3)	0.179 (4)	−0.016 (2)	0.062 (3)	0.019 (2)
N1	0.0416 (11)	0.0765 (14)	0.0671 (13)	−0.0124 (10)	−0.0039 (9)	−0.0003 (10)
N2	0.0349 (10)	0.0998 (18)	0.0827 (15)	−0.0066 (11)	−0.0002 (10)	−0.0018 (13)
O1	0.0910 (14)	0.0613 (12)	0.0898 (13)	−0.0124 (10)	0.0409 (11)	0.0029 (9)
O2	0.0688 (11)	0.0807 (12)	0.0641 (10)	−0.0032 (9)	0.0352 (9)	0.0054 (9)
Cl1	0.1182 (7)	0.1091 (7)	0.1002 (6)	−0.0457 (5)	0.0485 (5)	0.0149 (5)
Se1	0.03892 (14)	0.0867 (2)	0.0777 (2)	0.00811 (12)	0.01107 (11)	−0.00725 (13)

C1—C2	1.380 (4)	C14—H14	0.9300
C1—C6	1.387 (3)	C15—H15	0.9300
C1—H1	0.9300	C16—C23	1.509 (3)
C2—C3	1.374 (4)	C16—C17	1.522 (3)
C2—H2	0.9300	C16—H16	0.9800
C3—C4	1.364 (5)	C17—C18	1.372 (3)
C3—H3	0.9300	C17—C22	1.372 (3)
C4—C5	1.381 (4)	C18—C19	1.386 (3)
C4—H4	0.9300	C18—H18	0.9300
C5—C6	1.385 (3)	C19—C20	1.371 (5)
C5—H5	0.9300	C19—H19	0.9300
C6—C7	1.476 (3)	C20—C21	1.338 (5)
C7—C8	1.364 (3)	C20—H20	0.9300
C7—N1	1.392 (3)	C21—C22	1.386 (4)
C8—C9	1.513 (3)	C21—H21	0.9300
C8—Se1	1.838 (2)	C22—H22	0.9300
C9—C10	1.518 (3)	C23—O1	1.198 (3)
C9—C16	1.542 (3)	C23—O2	1.320 (3)
C9—H9	0.9800	C24—C25	1.448 (5)
C10—C11	1.382 (3)	C24—O2	1.449 (3)
C10—C15	1.384 (3)	C24—H24A	0.9700
C11—C12	1.379 (3)	C24—H24B	0.9700
C11—H11	0.9300	C25—H25A	0.9600
C12—C13	1.367 (4)	C25—H25B	0.9600
C12—H12	0.9300	C25—H25C	0.9600
C13—C14	1.368 (3)	N1—N2	1.263 (3)
C13—Cl1	1.736 (2)	N2—Se1	1.874 (2)
C14—C15	1.374 (3)
C2—C1—C6	119.8 (3)	C14—C15—H15	119.4
C2—C1—H1	120.1	C10—C15—H15	119.4
C6—C1—H1	120.1	C23—C16—C17	109.90 (17)
C3—C2—C1	120.5 (3)	C23—C16—C9	110.70 (17)
C3—C2—H2	119.7	C17—C16—C9	111.81 (17)
C1—C2—H2	119.7	C23—C16—H16	108.1
C4—C3—C2	119.8 (3)	C17—C16—H16	108.1
C4—C3—H3	120.1	C9—C16—H16	108.1
C2—C3—H3	120.1	C18—C17—C22	118.9 (2)
C3—C4—C5	120.6 (3)	C18—C17—C16	121.6 (2)
C3—C4—H4	119.7	C22—C17—C16	119.5 (2)
C5—C4—H4	119.7	C17—C18—C19	120.3 (3)
C4—C5—C6	120.0 (3)	C17—C18—H18	119.8
C4—C5—H5	120.0	C19—C18—H18	119.8
C6—C5—H5	120.0	C20—C19—C18	119.7 (3)
C5—C6—C1	119.2 (2)	C20—C19—H19	120.2
C5—C6—C7	119.2 (2)	C18—C19—H19	120.2
C1—C6—C7	121.5 (2)	C21—C20—C19	120.3 (3)
C8—C7—N1	115.0 (2)	C21—C20—H20	119.8
C8—C7—C6	128.22 (19)	C19—C20—H20	119.8
N1—C7—C6	116.80 (19)	C20—C21—C22	120.6 (3)
C7—C8—C9	127.0 (2)	C20—C21—H21	119.7
C7—C8—Se1	109.56 (15)	C22—C21—H21	119.7
C9—C8—Se1	123.19 (16)	C17—C22—C21	120.2 (3)
C8—C9—C10	109.59 (16)	C17—C22—H22	119.9
C8—C9—C16	112.45 (17)	C21—C22—H22	119.9
C10—C9—C16	112.21 (16)	O1—C23—O2	125.4 (2)
C8—C9—H9	107.4	O1—C23—C16	124.2 (2)
C10—C9—H9	107.4	O2—C23—C16	110.4 (2)
C16—C9—H9	107.4	C25—C24—O2	110.1 (3)
C11—C10—C15	118.2 (2)	C25—C24—H24A	109.6
C11—C10—C9	119.7 (2)	O2—C24—H24A	109.6
C15—C10—C9	122.06 (19)	C25—C24—H24B	109.6
C12—C11—C10	121.1 (2)	O2—C24—H24B	109.6
C12—C11—H11	119.5	H24A—C24—H24B	108.2
C10—C11—H11	119.5	C24—C25—H25A	109.5
C13—C12—C11	119.1 (2)	C24—C25—H25B	109.5
C13—C12—H12	120.4	H25A—C25—H25B	109.5
C11—C12—H12	120.4	C24—C25—H25C	109.5
C14—C13—C12	121.2 (2)	H25A—C25—H25C	109.5
C14—C13—Cl1	119.2 (2)	H25B—C25—H25C	109.5
C12—C13—Cl1	119.6 (2)	N2—N1—C7	117.5 (2)
C13—C14—C15	119.3 (2)	N1—N2—Se1	111.03 (15)
C13—C14—H14	120.4	C23—O2—C24	119.0 (2)
C15—C14—H14	120.4	C8—Se1—N2	86.93 (10)
C14—C15—C10	121.2 (2)
C6—C1—C2—C3	−0.4 (4)	C11—C10—C15—C14	1.0 (3)
C1—C2—C3—C4	0.7 (5)	C9—C10—C15—C14	178.84 (19)
C2—C3—C4—C5	−0.1 (5)	C8—C9—C16—C23	−50.6 (2)
C3—C4—C5—C6	−0.7 (5)	C10—C9—C16—C23	−174.72 (17)
C4—C5—C6—C1	1.0 (4)	C8—C9—C16—C17	−173.52 (18)
C4—C5—C6—C7	179.0 (2)	C10—C9—C16—C17	62.4 (2)
C2—C1—C6—C5	−0.5 (4)	C23—C16—C17—C18	−66.8 (3)
C2—C1—C6—C7	−178.4 (2)	C9—C16—C17—C18	56.6 (3)
C5—C6—C7—C8	129.5 (3)	C23—C16—C17—C22	112.2 (3)
C1—C6—C7—C8	−52.6 (3)	C9—C16—C17—C22	−124.4 (2)
C5—C6—C7—N1	−48.6 (3)	C22—C17—C18—C19	1.4 (4)
C1—C6—C7—N1	129.3 (2)	C16—C17—C18—C19	−179.6 (2)
N1—C7—C8—C9	174.8 (2)	C17—C18—C19—C20	−0.1 (4)
C6—C7—C8—C9	−3.3 (4)	C18—C19—C20—C21	−1.4 (5)
N1—C7—C8—Se1	−0.1 (2)	C19—C20—C21—C22	1.6 (6)
C6—C7—C8—Se1	−178.24 (18)	C18—C17—C22—C21	−1.3 (4)
C7—C8—C9—C10	−91.3 (3)	C16—C17—C22—C21	179.7 (3)
Se1—C8—C9—C10	83.0 (2)	C20—C21—C22—C17	−0.2 (6)
C7—C8—C9—C16	143.2 (2)	C17—C16—C23—O1	82.5 (3)
Se1—C8—C9—C16	−42.5 (2)	C9—C16—C23—O1	−41.5 (3)
C8—C9—C10—C11	101.5 (2)	C17—C16—C23—O2	−97.2 (2)
C16—C9—C10—C11	−132.8 (2)	C9—C16—C23—O2	138.78 (19)
C8—C9—C10—C15	−76.3 (2)	C8—C7—N1—N2	0.5 (3)
C16—C9—C10—C15	49.4 (2)	C6—C7—N1—N2	178.9 (2)
C15—C10—C11—C12	−1.1 (3)	C7—N1—N2—Se1	−0.7 (3)
C9—C10—C11—C12	−178.98 (19)	O1—C23—O2—C24	2.6 (4)
C10—C11—C12—C13	−0.1 (4)	C16—C23—O2—C24	−177.8 (2)
C11—C12—C13—C14	1.5 (4)	C25—C24—O2—C23	115.2 (3)
C11—C12—C13—Cl1	−178.78 (18)	C7—C8—Se1—N2	−0.22 (17)
C12—C13—C14—C15	−1.5 (4)	C9—C8—Se1—N2	−175.37 (18)
Cl1—C13—C14—C15	178.69 (18)	N1—N2—Se1—C8	0.5 (2)
C13—C14—C15—C10	0.3 (3)