Diethyl 2-[(4-nitro-phen-yl)(4-phenyl-1,2,3-selenadiazol-5-yl)meth-yl]malonate.

In the title compound, C(22)H(21)N(3)O(6)Se, the heterocyclic ring makes dihedral angles of 50.03 (11) and 67.75 (11)°, respectively, with the benzene and phenyl rings. The terminal C atoms of the ester groups are disordered over two positions: the site occupancies for the C atoms are 0.62 (3)/0.38 (3) and 0.48 (3)/0.52 (3). In the crystal structure, weak intra- and inter-molecular C-H⋯O inter-actions are observed.

Related literature

For biological activities, see: El-Kashef et al. (1986 ▶); El-Bahaie et al. (1990 ▶). For closely related compounds, see: Bertini et al. (1984 ▶); Gunasekaran et al. (2007 ▶).

Experimental

Crystal data

C22H21N3O6Se

M = 502.38

Triclinic,

a = 9.9530 (6) Å

b = 10.5220 (6) Å

c = 12.2305 (7) Å

α = 79.350 (3)°

β = 74.632 (3)°

γ = 67.632 (3)°

V = 1137.05 (11) Å3

Z = 2

Mo Kα radiation

μ = 1.69 mm−1

T = 295 (2) K

0.23 × 0.17 × 0.16 mm

Data collection

Bruker APEXII area-detector diffractometer

Absorption correction: multi-scan (; Sheldrick, 1996 ▶) T min = 0.697, T max = 0.773

30194 measured reflections

4477 independent reflections

3053 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.161

S = 1.04

4477 reflections

313 parameters

4 restraints

H-atom parameters constrained

Δρmax = 0.93 e Å−3

Δρmin = −0.80 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680800706X/is2278sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680800706X/is2278Isup2.hkl

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

C22H21N3O6Se	Z = 2
Mr = 502.38	F000 = 512
Triclinic, P1	Dx = 1.467 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 9.9530 (6) Å	Cell parameters from 8446 reflections
b = 10.5220 (6) Å	θ = 1.7–26º
c = 12.2305 (7) Å	µ = 1.69 mm−1
α = 79.350 (3)º	T = 295 (2) K
β = 74.632 (3)º	Block, colourless
γ = 67.632 (3)º	0.23 × 0.17 × 0.16 mm
V = 1137.05 (11) Å3

Bruker SMART APEX area-detector diffractometer	4477 independent reflections
Radiation source: fine-focus sealed tube	3053 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.028
T = 295(2) K	θmax = 26.1º
ω and φ scans	θmin = 1.7º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −12→12
Tmin = 0.697, Tmax = 0.773	k = −12→12
30194 measured reflections	l = −15→15

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.054	H-atom parameters constrained
wR(F2) = 0.161	w = 1/[σ2(Fo2) + (0.0776P)2 + 0.9842P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
4477 reflections	Δρmax = 0.93 e Å−3
313 parameters	Δρmin = −0.80 e Å−3
4 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

	x	y	z	Uiso*/Ueq	Occ. (<1)
Se1	1.00900 (5)	0.21345 (6)	0.44996 (4)	0.0888 (3)
O1	1.5749 (5)	0.1019 (4)	−0.0847 (4)	0.1160 (15)
O2	1.6666 (5)	0.0959 (5)	0.0564 (5)	0.1327 (17)
O4	0.7916 (3)	0.6035 (4)	0.4808 (2)	0.0859 (10)
O6	1.0425 (4)	0.6499 (3)	0.1149 (2)	0.0859 (10)
N1	0.8397 (5)	0.1628 (5)	0.5006 (4)	0.0939 (13)
N2	0.7447 (4)	0.2286 (4)	0.4410 (3)	0.0753 (10)
N3	1.5628 (6)	0.1283 (4)	0.0109 (5)	0.0929 (14)
C1	0.7808 (4)	0.3215 (4)	0.3527 (3)	0.0558 (9)
C2	0.9155 (4)	0.3332 (4)	0.3410 (3)	0.0521 (8)
C3	0.6670 (4)	0.4007 (4)	0.2854 (3)	0.0542 (9)
C4	0.5213 (5)	0.4674 (5)	0.3410 (4)	0.0686 (11)
H4	0.4952	0.4563	0.4201	0.082*
C5	0.4156 (5)	0.5494 (5)	0.2804 (5)	0.0807 (13)
H5	0.3193	0.5953	0.3187	0.097*
C6	0.4514 (6)	0.5637 (5)	0.1641 (5)	0.0837 (14)
H6	0.3801	0.6198	0.1231	0.100*
C7	0.5930 (6)	0.4949 (5)	0.1085 (4)	0.0796 (13)
H7	0.6168	0.5031	0.0293	0.095*
C8	0.7013 (5)	0.4133 (5)	0.1679 (3)	0.0640 (10)
H8	0.7970	0.3671	0.1288	0.077*
C9	0.9818 (4)	0.4288 (4)	0.2556 (3)	0.0495 (8)
H9	0.9199	0.4661	0.1987	0.059*
C10	1.1371 (4)	0.3504 (4)	0.1923 (3)	0.0509 (8)
C11	1.1559 (5)	0.3109 (4)	0.0853 (3)	0.0627 (10)
H11	1.0739	0.3346	0.0529	0.075*
C12	1.2940 (5)	0.2375 (5)	0.0274 (4)	0.0738 (12)
H12	1.3063	0.2109	−0.0441	0.089*
C13	1.4136 (5)	0.2034 (4)	0.0754 (4)	0.0696 (12)
C14	1.4005 (5)	0.2414 (4)	0.1802 (4)	0.0677 (11)
H14	1.4837	0.2182	0.2110	0.081*
C15	1.2595 (4)	0.3154 (4)	0.2393 (3)	0.0592 (9)
H15	1.2477	0.3413	0.3109	0.071*
C16	0.9754 (4)	0.5531 (4)	0.3084 (3)	0.0529 (9)
H16	1.0474	0.5205	0.3577	0.064*
C17	0.8230 (4)	0.6224 (4)	0.3794 (3)	0.0574 (9)
O3	0.7304 (3)	0.7037 (3)	0.3154 (3)	0.0766 (8)
C18	0.5803 (5)	0.7789 (5)	0.3722 (6)	0.110 (2)
H18A	0.5602	0.7413	0.4510	0.132*	0.62 (3)
H18B	0.5088	0.7732	0.3345	0.132*	0.62 (3)
H18C	0.5834	0.7912	0.4481	0.132*	0.38 (3)
H18D	0.5213	0.7210	0.3811	0.132*	0.38 (3)
C19	0.571 (2)	0.9256 (10)	0.366 (2)	0.150 (8)	0.62 (3)
H19A	0.6297	0.9317	0.4139	0.226*	0.62 (3)
H19B	0.4690	0.9830	0.3907	0.226*	0.62 (3)
H19C	0.6074	0.9561	0.2886	0.226*	0.62 (3)
C19A	0.500 (3)	0.917 (2)	0.318 (2)	0.140 (12)	0.38 (3)
H19D	0.5704	0.9573	0.2711	0.209*	0.38 (3)
H19E	0.4360	0.9769	0.3760	0.209*	0.38 (3)
H19F	0.4407	0.9071	0.2717	0.209*	0.38 (3)
C20	1.0180 (4)	0.6576 (4)	0.2149 (3)	0.0580 (10)
O5	1.0258 (4)	0.7581 (3)	0.2602 (3)	0.0796 (9)
C21	1.0583 (9)	0.8667 (6)	0.1809 (6)	0.131 (3)
H21A	1.0011	0.8895	0.1224	0.157*	0.48 (3)
H21B	1.1629	0.8346	0.1442	0.157*	0.48 (3)
H21C	1.0677	0.8480	0.1040	0.157*	0.52 (3)
H21D	1.1521	0.8705	0.1864	0.157*	0.52 (3)
C22	1.022 (4)	0.9937 (15)	0.2377 (14)	0.109 (8)	0.48 (3)
H22A	0.9262	1.0138	0.2880	0.164*	0.48 (3)
H22B	1.0221	1.0702	0.1810	0.164*	0.48 (3)
H22C	1.0961	0.9786	0.2806	0.164*	0.48 (3)
C22A	0.937 (2)	1.0027 (12)	0.205 (2)	0.152 (8)	0.52 (3)
H22D	0.8533	1.0101	0.1765	0.228*	0.52 (3)
H22E	0.9727	1.0763	0.1694	0.228*	0.52 (3)
H22F	0.9072	1.0087	0.2862	0.228*	0.52 (3)

	U11	U22	U33	U12	U13	U23
Se1	0.0812 (4)	0.1012 (4)	0.0863 (4)	−0.0446 (3)	−0.0377 (3)	0.0424 (3)
O1	0.116 (3)	0.095 (3)	0.110 (3)	−0.042 (2)	0.047 (3)	−0.035 (2)
O2	0.067 (2)	0.126 (4)	0.170 (5)	−0.014 (2)	0.018 (3)	−0.035 (3)
O4	0.0721 (19)	0.109 (2)	0.0520 (17)	−0.0186 (18)	0.0079 (14)	−0.0072 (16)
O6	0.125 (3)	0.082 (2)	0.0519 (18)	−0.051 (2)	−0.0073 (17)	0.0087 (14)
N1	0.091 (3)	0.103 (3)	0.085 (3)	−0.051 (2)	−0.023 (2)	0.041 (2)
N2	0.070 (2)	0.082 (2)	0.070 (2)	−0.039 (2)	−0.0106 (18)	0.0203 (19)
N3	0.076 (3)	0.067 (3)	0.115 (4)	−0.029 (2)	0.025 (3)	−0.014 (3)
C1	0.059 (2)	0.060 (2)	0.049 (2)	−0.0287 (18)	−0.0026 (16)	−0.0018 (16)
C2	0.056 (2)	0.054 (2)	0.0456 (19)	−0.0232 (17)	−0.0087 (16)	0.0014 (15)
C3	0.054 (2)	0.058 (2)	0.055 (2)	−0.0286 (18)	−0.0118 (17)	0.0014 (17)
C4	0.061 (3)	0.082 (3)	0.066 (3)	−0.033 (2)	−0.004 (2)	−0.011 (2)
C5	0.055 (3)	0.082 (3)	0.109 (4)	−0.022 (2)	−0.021 (3)	−0.018 (3)
C6	0.080 (3)	0.076 (3)	0.108 (4)	−0.035 (3)	−0.047 (3)	0.015 (3)
C7	0.087 (3)	0.100 (3)	0.068 (3)	−0.052 (3)	−0.032 (2)	0.017 (2)
C8	0.060 (2)	0.080 (3)	0.059 (2)	−0.037 (2)	−0.0125 (19)	0.002 (2)
C9	0.0473 (19)	0.054 (2)	0.0480 (19)	−0.0215 (16)	−0.0091 (15)	0.0014 (15)
C10	0.052 (2)	0.0492 (19)	0.049 (2)	−0.0221 (17)	−0.0031 (16)	−0.0016 (15)
C11	0.065 (2)	0.071 (3)	0.053 (2)	−0.030 (2)	−0.0024 (19)	−0.0099 (19)
C12	0.083 (3)	0.077 (3)	0.061 (2)	−0.038 (3)	0.010 (2)	−0.018 (2)
C13	0.064 (3)	0.051 (2)	0.080 (3)	−0.025 (2)	0.020 (2)	−0.016 (2)
C14	0.053 (2)	0.057 (2)	0.087 (3)	−0.0197 (19)	−0.009 (2)	0.000 (2)
C15	0.054 (2)	0.057 (2)	0.061 (2)	−0.0173 (18)	−0.0054 (18)	−0.0079 (18)
C16	0.052 (2)	0.051 (2)	0.051 (2)	−0.0203 (17)	−0.0052 (16)	0.0026 (16)
C17	0.054 (2)	0.052 (2)	0.061 (2)	−0.0203 (18)	−0.0008 (18)	−0.0071 (18)
O3	0.0510 (16)	0.0754 (19)	0.0778 (19)	−0.0092 (14)	−0.0015 (14)	0.0076 (15)
C18	0.054 (3)	0.088 (4)	0.148 (5)	−0.004 (3)	0.004 (3)	0.003 (4)
C19	0.089 (11)	0.096 (9)	0.207 (18)	0.014 (7)	0.010 (11)	−0.036 (9)
C19A	0.083 (14)	0.159 (19)	0.119 (16)	−0.017 (14)	−0.001 (11)	0.041 (13)
C20	0.050 (2)	0.053 (2)	0.060 (2)	−0.0169 (17)	−0.0017 (17)	0.0025 (18)
O5	0.096 (2)	0.0653 (18)	0.0764 (19)	−0.0450 (17)	0.0138 (16)	−0.0137 (15)
C21	0.165 (6)	0.074 (4)	0.132 (5)	−0.070 (4)	0.049 (5)	−0.015 (3)
C22	0.134 (18)	0.069 (8)	0.116 (11)	−0.042 (9)	−0.006 (10)	0.000 (7)
C22A	0.168 (17)	0.117 (12)	0.181 (18)	−0.080 (13)	−0.056 (15)	0.053 (11)

Se1—C2	1.836 (4)	C14—H14	0.9300
Se1—N1	1.875 (4)	C15—H15	0.9300
O1—N3	1.216 (6)	C16—C17	1.510 (5)
O2—N3	1.208 (7)	C16—C20	1.525 (5)
O4—C17	1.195 (5)	C16—H16	0.9800
O6—C20	1.195 (5)	C17—O3	1.315 (5)
N1—N2	1.260 (5)	O3—C18	1.447 (5)
N2—C1	1.386 (5)	C18—C19	1.4991 (10)
N3—C13	1.472 (6)	C18—C19A	1.4992 (10)
C1—C2	1.361 (5)	C18—H18A	0.9700
C1—C3	1.476 (5)	C18—H18B	0.9700
C2—C9	1.514 (5)	C18—H18C	0.9700
C3—C8	1.379 (5)	C18—H18D	0.9700
C3—C4	1.392 (5)	C19—H19A	0.9600
C4—C5	1.374 (6)	C19—H19B	0.9600
C4—H4	0.9300	C19—H19C	0.9600
C5—C6	1.366 (7)	C19A—H19D	0.9600
C5—H5	0.9300	C19A—H19E	0.9600
C6—C7	1.368 (7)	C19A—H19F	0.9600
C6—H6	0.9300	C20—O5	1.316 (5)
C7—C8	1.380 (6)	O5—C21	1.434 (6)
C7—H7	0.9300	C21—C22	1.4989 (10)
C8—H8	0.9300	C21—C22A	1.4990 (10)
C9—C10	1.517 (5)	C21—H21A	0.9700
C9—C16	1.535 (5)	C21—H21B	0.9700
C9—H9	0.9800	C21—H21C	0.9700
C10—C15	1.378 (5)	C21—H21D	0.9700
C10—C11	1.391 (5)	C22—H22A	0.9600
C11—C12	1.366 (6)	C22—H22B	0.9600
C11—H11	0.9300	C22—H22C	0.9600
C12—C13	1.363 (7)	C22A—H22D	0.9600
C12—H12	0.9300	C22A—H22E	0.9600
C13—C14	1.371 (6)	C22A—H22F	0.9600
C14—C15	1.392 (5)
C2—Se1—N1	87.20 (17)	C17—C16—C9	111.8 (3)
N2—N1—Se1	110.9 (3)	C20—C16—C9	110.1 (3)
N1—N2—C1	117.2 (4)	C17—C16—H16	108.4
O2—N3—O1	123.6 (5)	C20—C16—H16	108.4
O2—N3—C13	117.9 (6)	C9—C16—H16	108.4
O1—N3—C13	118.5 (6)	O4—C17—O3	124.9 (4)
C2—C1—N2	115.9 (4)	O4—C17—C16	123.6 (4)
C2—C1—C3	127.3 (3)	O3—C17—C16	111.5 (3)
N2—C1—C3	116.7 (3)	C17—O3—C18	117.6 (4)
C1—C2—C9	127.6 (3)	O3—C18—C19	106.1 (6)
C1—C2—Se1	108.8 (3)	O3—C18—C19A	118.2 (9)
C9—C2—Se1	123.7 (3)	O3—C18—H18A	110.5
C8—C3—C4	118.5 (4)	C19—C18—H18A	110.5
C8—C3—C1	121.9 (3)	O3—C18—H18B	110.5
C4—C3—C1	119.6 (3)	C19—C18—H18B	110.5
C5—C4—C3	120.7 (4)	H18A—C18—H18B	108.7
C5—C4—H4	119.6	O3—C18—H18C	107.7
C3—C4—H4	119.6	C19A—C18—H18C	107.7
C6—C5—C4	120.2 (4)	O3—C18—H18D	107.7
C6—C5—H5	119.9	C19A—C18—H18D	107.7
C4—C5—H5	119.9	H18C—C18—H18D	107.1
C5—C6—C7	119.5 (5)	C18—C19—H19A	109.5
C5—C6—H6	120.3	C18—C19—H19B	109.5
C7—C6—H6	120.3	C18—C19—H19C	109.5
C6—C7—C8	121.1 (4)	C18—C19A—H19D	109.5
C6—C7—H7	119.4	C18—C19A—H19E	109.5
C8—C7—H7	119.4	H19D—C19A—H19E	109.5
C3—C8—C7	119.8 (4)	C18—C19A—H19F	109.5
C3—C8—H8	120.1	H19D—C19A—H19F	109.5
C7—C8—H8	120.1	H19E—C19A—H19F	109.5
C2—C9—C10	111.3 (3)	O6—C20—O5	124.2 (4)
C2—C9—C16	112.8 (3)	O6—C20—C16	125.6 (4)
C10—C9—C16	112.6 (3)	O5—C20—C16	110.2 (3)
C2—C9—H9	106.5	C20—O5—C21	115.6 (4)
C10—C9—H9	106.5	O5—C21—C22	112.0 (7)
C16—C9—H9	106.5	O5—C21—C22A	110.3 (8)
C15—C10—C11	119.3 (3)	O5—C21—H21A	109.2
C15—C10—C9	121.5 (3)	C22—C21—H21A	109.2
C11—C10—C9	119.1 (3)	O5—C21—H21B	109.2
C12—C11—C10	120.4 (4)	C22—C21—H21B	109.2
C12—C11—H11	119.8	H21A—C21—H21B	107.9
C10—C11—H11	119.8	O5—C21—H21C	109.6
C13—C12—C11	119.4 (4)	C22A—C21—H21C	109.6
C13—C12—H12	120.3	O5—C21—H21D	109.6
C11—C12—H12	120.3	C22A—C21—H21D	109.6
C12—C13—C14	122.2 (4)	H21C—C21—H21D	108.1
C12—C13—N3	119.1 (5)	C21—C22—H22A	109.5
C14—C13—N3	118.7 (5)	C21—C22—H22B	109.5
C13—C14—C15	118.3 (4)	C21—C22—H22C	109.5
C13—C14—H14	120.9	C21—C22A—H22D	109.5
C15—C14—H14	120.9	C21—C22A—H22E	109.5
C10—C15—C14	120.4 (4)	H22D—C22A—H22E	109.5
C10—C15—H15	119.8	C21—C22A—H22F	109.5
C14—C15—H15	119.8	H22D—C22A—H22F	109.5
C17—C16—C20	109.6 (3)	H22E—C22A—H22F	109.5
C2—Se1—N1—N2	0.3 (4)	C10—C11—C12—C13	−0.2 (6)
Se1—N1—N2—C1	0.3 (6)	C11—C12—C13—C14	−0.5 (6)
N1—N2—C1—C2	−1.0 (6)	C11—C12—C13—N3	−178.0 (4)
N1—N2—C1—C3	−178.4 (4)	O2—N3—C13—C12	−178.0 (5)
N2—C1—C2—C9	−177.9 (4)	O1—N3—C13—C12	1.8 (6)
C3—C1—C2—C9	−0.8 (6)	O2—N3—C13—C14	4.4 (6)
N2—C1—C2—Se1	1.1 (4)	O1—N3—C13—C14	−175.8 (4)
C3—C1—C2—Se1	178.2 (3)	C12—C13—C14—C15	0.9 (6)
N1—Se1—C2—C1	−0.8 (3)	N3—C13—C14—C15	178.4 (4)
N1—Se1—C2—C9	178.3 (3)	C11—C10—C15—C14	0.1 (5)
C2—C1—C3—C8	50.7 (6)	C9—C10—C15—C14	178.9 (3)
N2—C1—C3—C8	−132.2 (4)	C13—C14—C15—C10	−0.7 (6)
C2—C1—C3—C4	−127.9 (4)	C2—C9—C16—C17	−48.0 (4)
N2—C1—C3—C4	49.2 (5)	C10—C9—C16—C17	−175.1 (3)
C8—C3—C4—C5	−3.1 (6)	C2—C9—C16—C20	−170.0 (3)
C1—C3—C4—C5	175.6 (4)	C10—C9—C16—C20	62.9 (4)
C3—C4—C5—C6	1.7 (7)	C20—C16—C17—O4	−138.2 (4)
C4—C5—C6—C7	0.5 (7)	C9—C16—C17—O4	99.5 (5)
C5—C6—C7—C8	−1.3 (7)	C20—C16—C17—O3	42.6 (4)
C4—C3—C8—C7	2.3 (6)	C9—C16—C17—O3	−79.7 (4)
C1—C3—C8—C7	−176.4 (4)	O4—C17—O3—C18	1.7 (6)
C6—C7—C8—C3	−0.1 (7)	C16—C17—O3—C18	−179.0 (4)
C1—C2—C9—C10	−128.4 (4)	C17—O3—C18—C19	105.5 (15)
Se1—C2—C9—C10	52.8 (4)	C17—O3—C18—C19A	149 (2)
C1—C2—C9—C16	103.8 (4)	C17—C16—C20—O6	−118.3 (4)
Se1—C2—C9—C16	−75.0 (4)	C9—C16—C20—O6	5.1 (6)
C2—C9—C10—C15	−81.3 (4)	C17—C16—C20—O5	62.4 (4)
C16—C9—C10—C15	46.6 (4)	C9—C16—C20—O5	−174.3 (3)
C2—C9—C10—C11	97.5 (4)	O6—C20—O5—C21	3.5 (7)
C16—C9—C10—C11	−134.6 (3)	C16—C20—O5—C21	−177.2 (5)
C15—C10—C11—C12	0.3 (6)	C20—O5—C21—C22	163.5 (15)
C9—C10—C11—C12	−178.5 (4)	C20—O5—C21—C22A	121.8 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C22A—H22D···O2i	0.96	2.47	3.38 (4)	159
C11—H11···O6ii	0.93	2.56	3.410 (6)	152
C18—H18A···O4	0.97	2.29	2.686 (7)	103
C21—H21C···O6	0.97	2.17	2.627 (6)	107

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C22A—H22D⋯O2i	0.96	2.47	3.38 (4)	159
C11—H11⋯O6ii	0.93	2.56	3.410 (6)	152
C18—H18A⋯O4	0.97	2.29	2.686 (7)	103
C21—H21C⋯O6	0.97	2.17	2.627 (6)	107

Symmetry codes: (i) ; (ii) .