Ethyl 3-(4-chloro­phen­yl)-2-phenyl-3-(4-phenyl-1,2,3-selena­diazol-5-yl)propano­ate

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

doi:10.1107/S1600536813017790

organic compounds

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ISSN: 2056-9890

Volume 69| Part 8| August 2013| Page o1239

doi:10.1107/S1600536813017790

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Ethyl 3-(4-chlorophenyl)-2-phenyl-3-(4-phenyl-1,2,3-selenadiazol-5-yl)propanoate

P. Sugumar,^a S. Sankari,^b P. Manisankar,^c V. Thiruselvam ^a 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 (Autonomous), Fairlands, Salem 636 016, India, and ^cDepartment of Industrial Chemistry, Alagappa University, Karaikudi 630 003, India
^*Correspondence e-mail: mnpsy2004@yahoo.com

(Received 14 June 2013; accepted 28 June 2013; online 10 July 2013)

In the title compound, C₂₅H₂₁ClN₂O₂Se, the selenadiazole 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_r = 495.85
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.037
wR(F²) = 0.107
S = 1.02
5764 reflections
280 parameters
H-atom parameters constrained
Δρ_max = 0.42 e Å⁻³
Δρ_min = −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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813017790/ng5333sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536813017790/ng5333Isup3.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). The crystal structure of the title compound is carried out to elucidate the conformational status of the molecule.

The ORTEP plot of the molecule is shown in Fig.1. The selenadiazol ring is planar[with maximum deviation for the atom N2 is -0.004 (2) Å]. The attached phenyl ring is twisted away at an angle of 50.6 (1)° with respect to selenadiazol ring. The bond lengths [Se1—N2] 1.874 (2) Å, [Se1—C8] 1.838 (2) Å & [Cl1—C13] 1.736 (2)° are comparable with the values reported in the literature (Marx et al. 2008; Muthukumaran et al. 2011). The bond C9—C16 is slightly lengthened due to streic interaction between the phenyl and chlorophenyl rings.

The dihedral angle between the selenadiazol and chlorophenyl ring is 74.3 (1)°. The propanoate group assumes an extended conformation which can be seen from the torsion angle (C16—C23—O2—C24) value of -177.8 (2)°.

Related literature top

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

Experimental top

A mixture of ethyl 3-(4-chlorophenyl)-5-oxo-2,5-diphenylpentanoate (1 mM), semicarbazide hydrochloride(2 mM) and sodium acetate (3 mM) in ethanol (10 ml) was refluxed for 4 hrs. 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 mM) and SeO₂ (2 mM) in tetrahydrofuran (10 ml) were refluxed on a water bath for 1hr. 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 ethyl-3-(4-chlorophenyl)-2-phenyl-3- (4-phenyl-1,2, 3-selenadiazol-5-yl)propanoate.

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.

Ethyl 3-(4-chlorophenyl)-2-phenyl-3-(4-phenyl-1,2,3-selenadiazol-5-yl)propanoate top

Crystal data top

C₂₅H₂₁ClN₂O₂Se	F(000) = 1008
M_r = 495.85	D_x = 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

Data collection top

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

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.107	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0471P)² + 0.6047P] where P = (F_o² + 2F_c²)/3
5764 reflections	(Δ/σ)_max = 0.002
280 parameters	Δρ_max = 0.42 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₂₅H₂₁ClN₂O₂Se	V = 2323.26 (10) Å³
M_r = 495.85	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.1337 (3) Å	µ = 1.76 mm⁻¹
b = 12.2267 (3) Å	T = 293 K
c = 16.4423 (4) Å	0.25 × 0.20 × 0.18 mm
β = 107.744 (1)°

Data collection top

Bruker SMART APEXII CCD diffractometer	5764 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	3745 reflections with I > 2σ(I)
T_min = 0.663, T_max = 0.729	R_int = 0.035
22323 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.107	H-atom parameters constrained
S = 1.02	Δρ_max = 0.42 e Å⁻³
5764 reflections	Δρ_min = −0.27 e Å⁻³
280 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	0.7760 (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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Experimental details

Crystal data
Chemical formula	C₂₅H₂₁ClN₂O₂Se
M_r	495.85
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	12.1337 (3), 12.2267 (3), 16.4423 (4)
β (°)	107.744 (1)
V (Å³)	2323.26 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.76
Crystal size (mm)	0.25 × 0.20 × 0.18

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.663, 0.729
No. of measured, independent and observed [I > 2σ(I)] reflections	22323, 5764, 3745
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.669

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.107, 1.02
No. of reflections	5764
No. of parameters	280
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.42, −0.27

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Acknowledgements

PS thanks the UGC, New Delhi, for financial support in the form of a Research Fellowship in Science for Meritorious Students. The authors thank the TBI Consultancy, University of Madras, India, for the data collection.

References

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