4-(4-Chloro-phen-yl)-5-[1-(4-chloro-phenyl)-2-methyl-2-nitro-prop-yl]-1,2,3-selenadiazole.

In the title compound, C(18)H(15)Cl(2)N(3)O(2)Se, the selenadiazole ring makes dihedral angles of 49.87 (3) and 55.70 (3)° with the two benzene rings. The dihedral angle between the two benzene rings is 11.90 (5)°. In the crystal structure, intra-molecular C-H⋯O and C-H⋯Se inter-actions and inter-molecular C-H⋯O, C-H⋯Cl and C-H⋯N inter-actions are observed.

Related literature

For related literature, see: Bertini et al. (1984 ▶); El-Bahaie et al. (1990 ▶); El-Kashef et al. (1986 ▶); Kuroda et al. (2001 ▶); Mellini & Merlino (1976a ▶,b ▶); Padmavathi et al. (2002 ▶); Saravanan et al. (2006 ▶); Gunasekaran et al. (2007 ▶).

Experimental

Crystal data

C18H15Cl2N3O2Se

M = 455.19

Triclinic,

a = 7.8352 (2) Å

b = 10.9208 (3) Å

c = 11.5507 (3) Å

α = 75.381 (1)°

β = 89.044 (1)°

γ = 83.331 (1)°

V = 949.80 (4) Å3

Z = 2

Mo Kα radiation

μ = 2.27 mm−1

T = 100 (2) K

0.33 × 0.18 × 0.17 mm

Data collection

Bruker Kappa APEXII diffractometer

Absorption correction: multi-scan (; Bruker, 2004 ▶) T min = 0.507, T max = 0.679

44785 measured reflections

9335 independent reflections

8074 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.064

S = 1.03

9335 reflections

237 parameters

H-atom parameters constrained

Δρmax = 0.57 e Å−3

Δρmin = −0.59 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807067487/is2267sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807067487/is2267Isup2.hkl

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

C18H15Cl2N3O2Se	Z = 2
Mr = 455.19	F000 = 456
Triclinic, P1	Dx = 1.592 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 7.8352 (2) Å	Cell parameters from 8302 reflections
b = 10.9208 (3) Å	θ = 2.7–34.5º
c = 11.5507 (3) Å	µ = 2.28 mm−1
α = 75.381 (1)º	T = 100 (2) K
β = 89.044 (1)º	Rectangular, colourless
γ = 83.331 (1)º	0.33 × 0.18 × 0.17 mm
V = 949.80 (4) Å3

Bruker Kappa-APEXII diffractometer	9335 independent reflections
Radiation source: fine-focus sealed tube	8074 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.028
T = 100(2) K	θmax = 36.7º
ω and φ scans	θmin = 1.8º
Absorption correction: multi-scan(SADABS; Bruker, 2004)	h = −13→13
Tmin = 0.507, Tmax = 0.679	k = −18→18
44785 measured reflections	l = −19→19

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)] = 0.026	H-atom parameters constrained
wR(F2) = 0.064	w = 1/[σ2(Fo2) + (0.031P)2 + 0.2243P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
9335 reflections	Δρmax = 0.57 e Å−3
237 parameters	Δρmin = −0.59 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

	x	y	z	Uiso*/Ueq
Se1	0.135681 (12)	0.147694 (9)	0.433060 (8)	0.01400 (3)
Cl1	0.22480 (5)	0.30162 (4)	−0.32615 (2)	0.03885 (8)
Cl2	0.23404 (5)	0.83872 (3)	0.28700 (3)	0.03592 (8)
O1	0.76068 (10)	0.34633 (8)	0.28931 (8)	0.02212 (15)
O2	0.67115 (11)	0.31526 (8)	0.12446 (7)	0.02317 (16)
N1	−0.02318 (11)	0.07149 (8)	0.36434 (7)	0.01542 (14)
N2	−0.01345 (10)	0.10161 (8)	0.25070 (7)	0.01371 (13)
N3	0.66526 (11)	0.30096 (8)	0.23302 (8)	0.01522 (14)
C1	0.10681 (11)	0.18154 (8)	0.20053 (8)	0.01114 (14)
C2	0.20509 (11)	0.21946 (8)	0.27992 (8)	0.01124 (14)
C3	0.12393 (12)	0.21352 (9)	0.06915 (8)	0.01239 (14)
C4	0.14006 (15)	0.11629 (10)	0.00999 (9)	0.01870 (18)
H4	0.1326	0.0309	0.0539	0.022*
C5	0.16690 (16)	0.14320 (11)	−0.11262 (9)	0.0233 (2)
H5	0.1771	0.0771	−0.1531	0.028*
C6	0.17854 (15)	0.26821 (12)	−0.17466 (9)	0.0219 (2)
C7	0.15700 (15)	0.36712 (10)	−0.11909 (9)	0.02036 (19)
H7	0.1612	0.4526	−0.1637	0.024*
C8	0.12902 (13)	0.33887 (9)	0.00348 (8)	0.01577 (16)
H8	0.1132	0.4058	0.0429	0.019*
C9	0.35407 (11)	0.29627 (8)	0.24434 (8)	0.01096 (13)
H9	0.3664	0.3057	0.1563	0.013*
C10	0.32202 (12)	0.43177 (9)	0.25869 (8)	0.01282 (14)
C11	0.35859 (14)	0.53150 (9)	0.16337 (9)	0.01794 (17)
H11	0.4016	0.5133	0.0914	0.022*
C12	0.33342 (17)	0.65705 (10)	0.17148 (10)	0.0229 (2)
H12	0.3586	0.7244	0.1059	0.027*
C13	0.27108 (16)	0.68213 (10)	0.27660 (10)	0.0217 (2)
C14	0.23240 (16)	0.58569 (10)	0.37302 (10)	0.0226 (2)
H14	0.1895	0.6045	0.4448	0.027*
C15	0.25739 (15)	0.46091 (10)	0.36297 (9)	0.01862 (18)
H15	0.2299	0.3941	0.4284	0.022*
C16	0.52730 (12)	0.22146 (9)	0.30124 (8)	0.01257 (14)
C17	0.55570 (13)	0.09225 (9)	0.27148 (10)	0.01807 (17)
H17A	0.6722	0.0520	0.2961	0.027*
H17B	0.5412	0.1041	0.1851	0.027*
H17C	0.4719	0.0377	0.3142	0.027*
C18	0.55381 (13)	0.20944 (10)	0.43339 (9)	0.01800 (17)
H18A	0.4704	0.1569	0.4795	0.027*
H18B	0.5375	0.2943	0.4487	0.027*
H18C	0.6706	0.1694	0.4575	0.027*

	U11	U22	U33	U12	U13	U23
Se1	0.01575 (4)	0.01765 (5)	0.00888 (4)	−0.00696 (3)	0.00236 (3)	−0.00175 (3)
Cl1	0.0533 (2)	0.0539 (2)	0.01020 (10)	−0.01394 (17)	0.00528 (11)	−0.00641 (12)
Cl2	0.0664 (2)	0.01200 (10)	0.02912 (14)	0.00353 (12)	−0.01822 (14)	−0.00708 (10)
O1	0.0197 (3)	0.0181 (3)	0.0286 (4)	−0.0094 (3)	−0.0035 (3)	−0.0024 (3)
O2	0.0213 (4)	0.0293 (4)	0.0161 (3)	−0.0055 (3)	0.0053 (3)	0.0003 (3)
N1	0.0150 (3)	0.0163 (3)	0.0150 (3)	−0.0058 (3)	0.0021 (3)	−0.0024 (3)
N2	0.0135 (3)	0.0140 (3)	0.0138 (3)	−0.0042 (3)	0.0012 (2)	−0.0027 (3)
N3	0.0130 (3)	0.0131 (3)	0.0177 (3)	−0.0032 (3)	0.0011 (3)	0.0003 (3)
C1	0.0116 (3)	0.0109 (3)	0.0108 (3)	−0.0018 (3)	0.0004 (3)	−0.0022 (3)
C2	0.0123 (3)	0.0116 (3)	0.0095 (3)	−0.0024 (3)	0.0007 (3)	−0.0017 (3)
C3	0.0143 (4)	0.0128 (4)	0.0102 (3)	−0.0031 (3)	−0.0005 (3)	−0.0025 (3)
C4	0.0277 (5)	0.0149 (4)	0.0149 (4)	−0.0051 (4)	−0.0010 (3)	−0.0050 (3)
C5	0.0345 (6)	0.0236 (5)	0.0146 (4)	−0.0046 (4)	0.0005 (4)	−0.0094 (4)
C6	0.0267 (5)	0.0298 (5)	0.0097 (4)	−0.0075 (4)	0.0004 (3)	−0.0042 (3)
C7	0.0276 (5)	0.0191 (4)	0.0130 (4)	−0.0084 (4)	−0.0025 (3)	0.0010 (3)
C8	0.0214 (4)	0.0132 (4)	0.0123 (4)	−0.0033 (3)	−0.0020 (3)	−0.0017 (3)
C9	0.0124 (3)	0.0111 (3)	0.0092 (3)	−0.0030 (3)	0.0004 (3)	−0.0016 (3)
C10	0.0156 (4)	0.0110 (3)	0.0113 (3)	−0.0024 (3)	−0.0012 (3)	−0.0013 (3)
C11	0.0264 (5)	0.0128 (4)	0.0137 (4)	−0.0052 (3)	0.0011 (3)	−0.0006 (3)
C12	0.0365 (6)	0.0120 (4)	0.0186 (4)	−0.0052 (4)	−0.0042 (4)	0.0003 (3)
C13	0.0328 (6)	0.0111 (4)	0.0212 (5)	−0.0001 (4)	−0.0095 (4)	−0.0044 (3)
C14	0.0352 (6)	0.0155 (4)	0.0178 (4)	0.0002 (4)	−0.0016 (4)	−0.0068 (3)
C15	0.0285 (5)	0.0138 (4)	0.0134 (4)	−0.0028 (4)	0.0017 (3)	−0.0031 (3)
C16	0.0122 (3)	0.0118 (3)	0.0133 (3)	−0.0045 (3)	0.0007 (3)	−0.0011 (3)
C17	0.0155 (4)	0.0130 (4)	0.0259 (5)	−0.0022 (3)	−0.0007 (3)	−0.0049 (3)
C18	0.0172 (4)	0.0223 (5)	0.0127 (4)	−0.0040 (3)	−0.0029 (3)	−0.0003 (3)

Se1—C2	1.8455 (9)	C9—C10	1.5220 (13)
Se1—N1	1.8652 (9)	C9—C16	1.5630 (12)
Cl1—C6	1.7360 (10)	C9—H9	1.0000
Cl2—C13	1.7350 (10)	C10—C11	1.3918 (13)
O1—N3	1.2216 (12)	C10—C15	1.3944 (13)
O2—N3	1.2247 (11)	C11—C12	1.3889 (15)
N1—N2	1.2734 (11)	C11—H11	0.9500
N2—C1	1.3795 (12)	C12—C13	1.3802 (16)
N3—C16	1.5451 (12)	C12—H12	0.9500
C1—C2	1.3765 (12)	C13—C14	1.3828 (16)
C1—C3	1.4762 (12)	C14—C15	1.3877 (14)
C2—C9	1.5075 (13)	C14—H14	0.9500
C3—C8	1.3923 (13)	C15—H15	0.9500
C3—C4	1.3938 (13)	C16—C18	1.5144 (13)
C4—C5	1.3895 (15)	C16—C17	1.5259 (13)
C4—H4	0.9500	C17—H17A	0.9800
C5—C6	1.3851 (17)	C17—H17B	0.9800
C5—H5	0.9500	C17—H17C	0.9800
C6—C7	1.3826 (16)	C18—H18A	0.9800
C7—C8	1.3901 (14)	C18—H18B	0.9800
C7—H7	0.9500	C18—H18C	0.9800
C8—H8	0.9500
C2—Se1—N1	87.45 (4)	C11—C10—C15	118.31 (9)
N2—N1—Se1	111.08 (6)	C11—C10—C9	118.61 (8)
N1—N2—C1	117.26 (8)	C15—C10—C9	123.07 (8)
O1—N3—O2	123.86 (9)	C12—C11—C10	121.26 (10)
O1—N3—C16	118.80 (8)	C12—C11—H11	119.4
O2—N3—C16	117.33 (8)	C10—C11—H11	119.4
C2—C1—N2	115.83 (8)	C13—C12—C11	118.80 (10)
C2—C1—C3	126.24 (8)	C13—C12—H12	120.6
N2—C1—C3	117.87 (8)	C11—C12—H12	120.6
C1—C2—C9	124.13 (8)	C12—C13—C14	121.63 (10)
C1—C2—Se1	108.37 (6)	C12—C13—Cl2	119.39 (9)
C9—C2—Se1	127.26 (6)	C14—C13—Cl2	118.95 (9)
C8—C3—C4	119.31 (8)	C13—C14—C15	118.74 (10)
C8—C3—C1	121.17 (8)	C13—C14—H14	120.6
C4—C3—C1	119.50 (8)	C15—C14—H14	120.6
C5—C4—C3	120.54 (10)	C14—C15—C10	121.25 (10)
C5—C4—H4	119.7	C14—C15—H15	119.4
C3—C4—H4	119.7	C10—C15—H15	119.4
C6—C5—C4	118.75 (10)	C18—C16—C17	111.81 (8)
C6—C5—H5	120.6	C18—C16—N3	107.47 (8)
C4—C5—H5	120.6	C17—C16—N3	106.56 (7)
C7—C6—C5	121.93 (9)	C18—C16—C9	116.40 (8)
C7—C6—Cl1	118.93 (9)	C17—C16—C9	110.03 (7)
C5—C6—Cl1	119.13 (9)	N3—C16—C9	103.77 (7)
C6—C7—C8	118.62 (10)	C16—C17—H17A	109.5
C6—C7—H7	120.7	C16—C17—H17B	109.5
C8—C7—H7	120.7	H17A—C17—H17B	109.5
C7—C8—C3	120.74 (9)	C16—C17—H17C	109.5
C7—C8—H8	119.6	H17A—C17—H17C	109.5
C3—C8—H8	119.6	H17B—C17—H17C	109.5
C2—C9—C10	114.26 (7)	C16—C18—H18A	109.5
C2—C9—C16	111.87 (7)	C16—C18—H18B	109.5
C10—C9—C16	114.10 (7)	H18A—C18—H18B	109.5
C2—C9—H9	105.2	C16—C18—H18C	109.5
C10—C9—H9	105.2	H18A—C18—H18C	109.5
C16—C9—H9	105.2	H18B—C18—H18C	109.5
C2—Se1—N1—N2	−0.27 (7)	Se1—C2—C9—C16	56.27 (10)
Se1—N1—N2—C1	−0.06 (10)	C2—C9—C10—C11	−130.65 (9)
N1—N2—C1—C2	0.52 (12)	C16—C9—C10—C11	98.86 (10)
N1—N2—C1—C3	177.82 (8)	C2—C9—C10—C15	49.27 (12)
N2—C1—C2—C9	174.02 (8)	C16—C9—C10—C15	−81.22 (11)
C3—C1—C2—C9	−3.01 (14)	C15—C10—C11—C12	0.63 (16)
N2—C1—C2—Se1	−0.69 (10)	C9—C10—C11—C12	−179.44 (10)
C3—C1—C2—Se1	−177.72 (7)	C10—C11—C12—C13	0.08 (17)
N1—Se1—C2—C1	0.52 (7)	C11—C12—C13—C14	−0.43 (18)
N1—Se1—C2—C9	−173.98 (8)	C11—C12—C13—Cl2	−178.47 (9)
C2—C1—C3—C8	−50.52 (14)	C12—C13—C14—C15	0.03 (18)
N2—C1—C3—C8	132.50 (10)	Cl2—C13—C14—C15	178.09 (9)
C2—C1—C3—C4	127.69 (11)	C13—C14—C15—C10	0.72 (18)
N2—C1—C3—C4	−49.29 (12)	C11—C10—C15—C14	−1.04 (16)
C8—C3—C4—C5	2.21 (16)	C9—C10—C15—C14	179.04 (10)
C1—C3—C4—C5	−176.03 (10)	O1—N3—C16—C18	−4.50 (11)
C3—C4—C5—C6	0.46 (18)	O2—N3—C16—C18	175.98 (8)
C4—C5—C6—C7	−2.80 (19)	O1—N3—C16—C17	−124.49 (9)
C4—C5—C6—Cl1	176.20 (9)	O2—N3—C16—C17	55.98 (10)
C5—C6—C7—C8	2.35 (18)	O1—N3—C16—C9	119.35 (9)
Cl1—C6—C7—C8	−176.64 (9)	O2—N3—C16—C9	−60.17 (10)
C6—C7—C8—C3	0.43 (16)	C2—C9—C16—C18	−74.54 (10)
C4—C3—C8—C7	−2.67 (15)	C10—C9—C16—C18	57.11 (10)
C1—C3—C8—C7	175.54 (9)	C2—C9—C16—C17	53.95 (10)
C1—C2—C9—C10	111.01 (10)	C10—C9—C16—C17	−174.40 (8)
Se1—C2—C9—C10	−75.30 (10)	C2—C9—C16—N3	167.63 (7)
C1—C2—C9—C16	−117.41 (9)	C10—C9—C16—N3	−60.71 (9)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O2	1.00	2.42	2.8271 (12)	104
C15—H15···Se1	0.95	2.86	3.5496 (10)	130
C18—H18A···Se1	0.98	2.70	3.4209 (10)	130
C7—H7···O1i	0.95	2.44	3.3757 (13)	167
C15—H15···Cl1ii	0.95	2.76	3.5923 (10)	147
C17—H17A···N1iii	0.98	2.57	3.4511 (13)	149
C17—H17A···N2iii	0.98	2.60	3.3919 (13)	138

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯O2	1.00	2.42	2.8271 (12)	104
C15—H15⋯Se1	0.95	2.86	3.5496 (10)	130
C18—H18A⋯Se1	0.98	2.70	3.4209 (10)	130
C7—H7⋯O1i	0.95	2.44	3.3757 (13)	167
C15—H15⋯Cl1ii	0.95	2.76	3.5923 (10)	147
C17—H17A⋯N1iii	0.98	2.57	3.4511 (13)	149
C17—H17A⋯N2iii	0.98	2.60	3.3919 (13)	138

Symmetry codes: (i) ; (ii) ; (iii) .