3-(4-Methyl-phen-yl)-1-phenyl-3-(4,5,6,7-tetra-hydro-1,2,3-benzoselenadiazol-4-yl)propan-1-one.

In the title compound, C(22)H(22)N(2)OSe, the fused six-membered ring of the 4,5,6,7-tetra-hydro-benzo[d][1,2,3] selenadiazole group adopts a near to envelope (E form) conformation and the five-membered 1,2,3-selenadiazole ring is essentially planar (r.m.s. deviation = 0.0059 Å). In the crystal, adjacent mol-ecules are inter-linked through weak inter-molecular C-H⋯π inter-actions.

Related literature

For bond lengths in compounds containing a 1,2,3-selenadiazole group, see: Arsenyan et al. (2007 ▶); Saravanan et al. (2006a ▶,b ▶, 2007 ▶, 2008 ▶); Marx et al. (2007 ▶, 2008a ▶,b ▶); Gunasekaran et al. (2007a ▶,b ▶). For biological applications of 1,2,3-selenadiazole derivatives, see: Kuroda et al. (2001 ▶); El-Bahaie et al. (1990 ▶); El-Kashef et al. (1986 ▶); Plano et al. (2010 ▶); Padmavathi et al. (2002 ▶). For ring puckering analysis, see: Cremer & Pople (1975 ▶). For C—H⋯π inter­actions, see: Desiraju & Steiner (1999 ▶).

Experimental

Crystal data

C22H22N2OSe

M = 409.38

Triclinic,

a = 8.1485 (9) Å

b = 9.7929 (9) Å

c = 12.1234 (13) Å

α = 98.707 (9)°

β = 96.387 (9)°

γ = 94.792 (9)°

V = 945.36 (17) Å3

Z = 2

Mo Kα radiation

μ = 2.00 mm−1

T = 293 K

0.5 × 0.40 × 0.25 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.585, T max = 1.000

8343 measured reflections

3339 independent reflections

2615 reflections with I > 2σ(I)

R int = 0.055

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.100

S = 1.00

3339 reflections

236 parameters

H-atom parameters constrained

Δρmax = 0.40 e Å−3

Δρmin = −0.66 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data reduction: CrysAlis RED; 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, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: PLATON.

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S160053681102174X/zl2374sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681102174X/zl2374Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681102174X/zl2374Isup3.cml

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

C22H22N2OSe	Z = 2
Mr = 409.38	F(000) = 420
Triclinic, P1	Dx = 1.438 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.1485 (9) Å	Cell parameters from 4672 reflections
b = 9.7929 (9) Å	θ = 2.9–29.2°
c = 12.1234 (13) Å	µ = 2.00 mm−1
α = 98.707 (9)°	T = 293 K
β = 96.387 (9)°	Block, blue
γ = 94.792 (9)°	0.5 × 0.40 × 0.25 mm
V = 945.36 (17) Å3

Oxford Diffraction Xcalibur Eos diffractometer	3339 independent reflections
Radiation source: fine-focus sealed tube	2615 reflections with I > 2σ(I)
graphite	Rint = 0.055
Detector resolution: 15.9821 pixels mm-1	θmax = 25.0°, θmin = 2.9°
ω scans	h = −9→9
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −11→11
Tmin = 0.585, Tmax = 1.000	l = −14→14
8343 measured reflections

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) = 0.100	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.050P)2] where P = (Fo2 + 2Fc2)/3
3339 reflections	(Δ/σ)max = 0.034
236 parameters	Δρmax = 0.40 e Å−3
0 restraints	Δρmin = −0.66 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
Se1	−0.19156 (4)	0.31704 (3)	−0.12511 (3)	0.05512 (16)
O1	0.3386 (3)	0.0336 (3)	0.32048 (18)	0.0610 (6)
N1	−0.0624 (3)	0.1746 (2)	0.0229 (2)	0.0448 (6)
N2	−0.2056 (3)	0.1974 (3)	−0.0175 (2)	0.0550 (7)
C1	0.0719 (3)	0.2396 (3)	−0.0161 (2)	0.0343 (6)
C2	0.0346 (3)	0.3218 (3)	−0.0942 (2)	0.0368 (6)
C3	0.1612 (4)	0.3990 (3)	−0.1498 (2)	0.0459 (7)
H3A	0.1697	0.4973	−0.1199	0.055*
H3B	0.1258	0.3873	−0.2300	0.055*
C4	0.3299 (3)	0.3453 (3)	−0.1294 (2)	0.0423 (7)
H4A	0.3314	0.2586	−0.1798	0.051*
H4B	0.4150	0.4117	−0.1461	0.051*
C5	0.3690 (3)	0.3219 (3)	−0.0084 (2)	0.0388 (6)
H5A	0.3656	0.4083	0.0420	0.047*
H5B	0.4804	0.2942	0.0028	0.047*
C6	0.2456 (3)	0.2097 (3)	0.0210 (2)	0.0326 (6)
H6	0.2626	0.1227	−0.0261	0.039*
C7	0.2761 (3)	0.1843 (3)	0.1445 (2)	0.0327 (6)
H7	0.1838	0.1185	0.1549	0.039*
C8	0.2757 (3)	0.3124 (3)	0.2321 (2)	0.0336 (6)
C9	0.1304 (4)	0.3465 (3)	0.2740 (2)	0.0442 (7)
H9	0.0321	0.2901	0.2473	0.053*
C10	0.1276 (4)	0.4621 (3)	0.3547 (2)	0.0503 (8)
H10	0.0278	0.4816	0.3810	0.060*
C11	0.2703 (4)	0.5492 (3)	0.3970 (2)	0.0501 (8)
C12	0.4156 (4)	0.5161 (3)	0.3552 (2)	0.0508 (8)
H12	0.5137	0.5727	0.3820	0.061*
C13	0.4181 (3)	0.4012 (3)	0.2750 (2)	0.0415 (7)
H13	0.5180	0.3823	0.2486	0.050*
C14	0.2685 (5)	0.6764 (4)	0.4855 (3)	0.0784 (12)
H14A	0.2668	0.7577	0.4500	0.118*
H14B	0.3660	0.6855	0.5393	0.118*
H14C	0.1714	0.6665	0.5229	0.118*
C15	0.4339 (3)	0.1113 (3)	0.1603 (2)	0.0381 (6)
H15A	0.4323	0.0374	0.0970	0.046*
H15B	0.5293	0.1774	0.1599	0.046*
C16	0.4547 (3)	0.0505 (3)	0.2673 (2)	0.0362 (6)
C17	0.6188 (3)	0.0024 (2)	0.3039 (2)	0.0328 (6)
C18	0.7605 (3)	0.0330 (3)	0.2545 (2)	0.0419 (7)
H18	0.7562	0.0860	0.1969	0.050*
C19	0.9086 (4)	−0.0160 (3)	0.2917 (3)	0.0579 (8)
H19	1.0040	0.0053	0.2594	0.069*
C20	0.9149 (4)	−0.0951 (3)	0.3752 (3)	0.0603 (9)
H20	1.0144	−0.1281	0.3990	0.072*
C21	0.7756 (4)	−0.1266 (3)	0.4247 (3)	0.0575 (9)
H21	0.7810	−0.1804	0.4817	0.069*
C22	0.6269 (4)	−0.0777 (3)	0.3890 (2)	0.0459 (7)
H22	0.5325	−0.0987	0.4223	0.055*

	U11	U22	U33	U12	U13	U23
Se1	0.0423 (2)	0.0661 (3)	0.0560 (2)	0.01699 (17)	−0.00317 (16)	0.00744 (17)
O1	0.0453 (13)	0.0959 (17)	0.0575 (14)	0.0249 (12)	0.0249 (11)	0.0392 (13)
N1	0.0341 (14)	0.0493 (15)	0.0504 (15)	0.0004 (11)	0.0051 (11)	0.0081 (12)
N2	0.0353 (15)	0.0650 (17)	0.0626 (17)	0.0015 (13)	0.0057 (12)	0.0061 (13)
C1	0.0360 (15)	0.0315 (14)	0.0331 (14)	0.0009 (12)	0.0043 (11)	−0.0008 (11)
C2	0.0379 (16)	0.0372 (15)	0.0332 (14)	0.0080 (12)	0.0015 (12)	−0.0011 (11)
C3	0.0564 (19)	0.0429 (16)	0.0401 (16)	0.0054 (14)	0.0033 (14)	0.0139 (13)
C4	0.0456 (18)	0.0457 (16)	0.0360 (15)	−0.0015 (13)	0.0094 (13)	0.0085 (13)
C5	0.0340 (15)	0.0472 (16)	0.0372 (15)	0.0014 (13)	0.0066 (12)	0.0123 (12)
C6	0.0319 (14)	0.0349 (14)	0.0311 (14)	0.0036 (11)	0.0060 (11)	0.0036 (11)
C7	0.0284 (14)	0.0356 (14)	0.0358 (14)	0.0026 (11)	0.0069 (11)	0.0093 (11)
C8	0.0378 (16)	0.0369 (15)	0.0291 (13)	0.0077 (12)	0.0063 (11)	0.0109 (11)
C9	0.0369 (16)	0.0501 (17)	0.0451 (17)	0.0063 (13)	0.0056 (13)	0.0049 (13)
C10	0.054 (2)	0.0575 (19)	0.0429 (17)	0.0220 (17)	0.0139 (15)	0.0045 (14)
C11	0.075 (2)	0.0421 (17)	0.0343 (16)	0.0160 (17)	0.0026 (15)	0.0064 (13)
C12	0.059 (2)	0.0469 (18)	0.0418 (17)	−0.0043 (15)	−0.0039 (15)	0.0045 (14)
C13	0.0398 (17)	0.0460 (16)	0.0385 (15)	0.0034 (13)	0.0058 (12)	0.0057 (13)
C14	0.110 (3)	0.058 (2)	0.063 (2)	0.023 (2)	0.005 (2)	−0.0098 (18)
C15	0.0382 (16)	0.0398 (15)	0.0397 (15)	0.0099 (13)	0.0106 (12)	0.0094 (12)
C16	0.0387 (16)	0.0383 (15)	0.0329 (14)	0.0055 (12)	0.0092 (12)	0.0054 (11)
C17	0.0357 (15)	0.0295 (13)	0.0316 (14)	0.0050 (11)	0.0031 (11)	−0.0003 (11)
C18	0.0355 (16)	0.0407 (16)	0.0492 (17)	0.0031 (13)	0.0058 (13)	0.0070 (13)
C19	0.0358 (18)	0.063 (2)	0.073 (2)	0.0031 (15)	0.0055 (15)	0.0082 (18)
C20	0.049 (2)	0.066 (2)	0.061 (2)	0.0204 (17)	−0.0099 (17)	0.0025 (17)
C21	0.072 (2)	0.063 (2)	0.0398 (17)	0.0220 (18)	−0.0018 (16)	0.0138 (15)
C22	0.0521 (18)	0.0523 (18)	0.0353 (15)	0.0132 (14)	0.0070 (13)	0.0079 (13)

N1—N2	1.266 (3)	C12—C11	1.383 (4)
N1—C1	1.384 (3)	C12—H12	0.9300
Se1—C2	1.834 (3)	C13—C12	1.375 (4)
Se1—N2	1.887 (3)	C13—C8	1.391 (4)
C1—C2	1.358 (4)	C13—H13	0.9300
C3—C2	1.506 (4)	C14—H14A	0.9600
C3—H3A	0.9700	C14—H14B	0.9600
C3—H3B	0.9700	C14—H14C	0.9600
C4—C5	1.521 (3)	C15—C16	1.506 (3)
C4—C3	1.521 (4)	C15—C7	1.531 (3)
C4—H4A	0.9700	C15—H15A	0.9700
C4—H4B	0.9700	C15—H15B	0.9700
C5—H5A	0.9700	O1—C16	1.216 (3)
C5—H5B	0.9700	C17—C22	1.386 (3)
C6—C1	1.502 (3)	C17—C18	1.390 (4)
C6—C5	1.535 (3)	C17—C16	1.498 (3)
C6—C7	1.552 (3)	C18—C19	1.390 (4)
C6—H6	0.9800	C18—H18	0.9300
C7—C8	1.517 (3)	C19—C20	1.364 (4)
C7—H7	0.9800	C19—H19	0.9300
C9—C8	1.386 (4)	C20—H20	0.9300
C9—C10	1.382 (4)	C21—C20	1.375 (5)
C9—H9	0.9300	C21—H21	0.9300
C10—C11	1.382 (4)	C22—C21	1.389 (4)
C10—H10	0.9300	C22—H22	0.9300
C11—C14	1.518 (4)
N1—N2—Se1	110.78 (19)	C10—C9—H9	119.1
N1—C1—C6	120.6 (2)	C10—C11—C14	121.7 (3)
N2—N1—C1	117.2 (2)	C11—C14—H14A	109.5
C1—C6—C5	109.0 (2)	C11—C14—H14B	109.5
C1—C6—C7	114.5 (2)	C11—C10—C9	121.4 (3)
C1—C6—H6	106.1	C11—C10—H10	119.3
C1—C2—C3	124.5 (2)	C11—C12—H12	119.3
C1—C2—Se1	109.5 (2)	C11—C14—H14C	109.5
C2—Se1—N2	86.70 (11)	C12—C11—C10	117.2 (3)
C2—C1—N1	115.8 (2)	C12—C11—C14	121.0 (3)
C2—C1—C6	123.5 (2)	C12—C13—C8	122.0 (3)
C2—C3—C4	110.6 (2)	C12—C13—H13	119.0
C2—C3—H3A	109.5	C13—C8—C7	122.8 (2)
C2—C3—H3B	109.5	C13—C12—C11	121.3 (3)
C3—C4—H4A	109.3	C13—C12—H12	119.3
C3—C4—H4B	109.3	H14A—C14—H14B	109.5
C3—C2—Se1	125.89 (19)	H14A—C14—H14C	109.5
H3A—C3—H3B	108.1	H14B—C14—H14C	109.5
C4—C5—C6	111.9 (2)	C15—C7—C6	109.07 (19)
C4—C5—H5A	109.2	C15—C7—H7	106.6
C4—C5—H5B	109.2	H15A—C15—H15B	107.7
H4A—C4—H4B	107.9	C16—C15—C7	113.9 (2)
C4—C3—H3A	109.5	C16—C15—H15A	108.8
C4—C3—H3B	109.5	C16—C15—H15B	108.8
C5—C6—C7	114.3 (2)	O1—C16—C17	120.1 (2)
C5—C6—H6	106.1	O1—C16—C15	121.0 (2)
C5—C4—C3	111.7 (2)	C17—C18—H18	120.2
C5—C4—H4A	109.3	C17—C22—H22	119.9
C5—C4—H4B	109.3	C17—C16—C15	118.8 (2)
H5A—C5—H5B	107.9	C18—C17—C16	122.5 (2)
C6—C7—H7	106.6	C18—C19—H19	119.8
C6—C5—H5A	109.2	C19—C18—C17	119.6 (3)
C6—C5—H5B	109.2	C19—C18—H18	120.2
C7—C6—H6	106.1	C19—C20—C21	120.7 (3)
C7—C15—H15A	108.8	C19—C20—H20	119.6
C7—C15—H15B	108.8	C20—C21—C22	119.6 (3)
C8—C9—C10	121.7 (3)	C20—C21—H21	120.2
C8—C9—H9	119.1	C20—C19—C18	120.3 (3)
C8—C13—H13	119.0	C20—C19—H19	119.8
C8—C7—C15	113.0 (2)	C21—C22—C17	120.2 (3)
C8—C7—C6	114.5 (2)	C21—C22—H22	119.9
C8—C7—H7	106.6	C21—C20—H20	119.6
C9—C10—H10	119.3	C22—C17—C18	119.5 (2)
C9—C8—C13	116.4 (3)	C22—C17—C16	118.0 (2)
C9—C8—C7	120.8 (2)	C22—C21—H21	120.2
N1—C1—C2—C3	−178.4 (2)	C7—C15—C16—C17	−167.7 (2)
N1—C1—C2—Se1	−0.9 (3)	C8—C13—C12—C11	−0.3 (4)
N2—N1—C1—C2	0.1 (4)	C8—C9—C10—C11	0.1 (4)
N2—N1—C1—C6	−175.4 (2)	C9—C10—C11—C12	0.1 (4)
N2—Se1—C2—C1	1.03 (19)	C9—C10—C11—C14	180.0 (3)
N2—Se1—C2—C3	178.5 (2)	C10—C9—C8—C13	−0.4 (4)
C1—N1—N2—Se1	0.7 (3)	C10—C9—C8—C7	179.4 (2)
C1—C6—C5—C4	−48.7 (3)	C12—C13—C8—C9	0.5 (4)
C1—C6—C7—C8	−70.1 (3)	C12—C13—C8—C7	−179.3 (2)
C1—C6—C7—C15	162.1 (2)	C13—C12—C11—C10	0.0 (4)
C2—Se1—N2—N1	−1.0 (2)	C13—C12—C11—C14	−179.9 (3)
C3—C4—C5—C6	63.0 (3)	C15—C7—C8—C9	−143.5 (2)
C4—C3—C2—C1	14.1 (4)	C15—C7—C8—C13	36.2 (3)
C4—C3—C2—Se1	−162.95 (19)	C16—C17—C18—C19	−179.4 (3)
C5—C6—C1—C2	20.0 (3)	C16—C17—C22—C21	179.0 (3)
C5—C6—C1—N1	−164.9 (2)	C16—C15—C7—C8	65.3 (3)
C5—C6—C7—C8	56.6 (3)	C16—C15—C7—C6	−166.1 (2)
C5—C6—C7—C15	−71.1 (3)	C17—C22—C21—C20	0.1 (4)
C5—C4—C3—C2	−42.7 (3)	C17—C18—C19—C20	0.8 (5)
C6—C1—C2—C3	−3.1 (4)	C18—C19—C20—C21	−0.6 (5)
C6—C1—C2—Se1	174.40 (19)	C18—C17—C16—O1	−172.4 (3)
C6—C7—C8—C9	90.8 (3)	C18—C17—C22—C21	0.1 (4)
C6—C7—C8—C13	−89.5 (3)	C18—C17—C16—C15	11.4 (4)
C7—C6—C5—C4	−178.3 (2)	C22—C17—C18—C19	−0.6 (4)
C7—C6—C1—C2	149.4 (2)	C22—C17—C16—O1	8.8 (4)
C7—C6—C1—N1	−35.5 (3)	C22—C17—C16—C15	−167.4 (2)
C7—C15—C16—O1	16.1 (4)	C22—C21—C20—C19	0.2 (5)