Intra- and inter­molecular Se...X (X = Se, O) inter­actions in selenium-containing heterocycles: 3-benzoyl­imino-5-(morpholin-4-yl)-1,2,4-diselen­azole

In the selenium-containing heterocyclic title compound {sys­tematic name: N-[5-(morpholin-4-yl)-3H-1,2,4-diselen­azol-3-yl­idene]benzamide}, C₁₃H₁₃N₃O₂Se₂, the five-membered 1,2,4-diselenazole ring and the amide group form a planar unit, but the phenyl ring plane is twisted by 22.12 (19)° relative to this plane. The five consecutive N—C bond lengths are all of similar lengths [1.316 (6)–1.358 (6) Å], indicating substantial delocalization along these bonds. The Se...O distance of 2.302 (3) Å, combined with a longer than usual amide C=O bond of 2.252 (5) Å, suggest a significant inter­action between the amide O atom and its adjacent Se atom. An analysis of related structures containing an Se—Se...X unit (X = Se, S, O) shows a strong correlation between the Se—Se bond length and the strength of the Se...X inter­action. When X = O, the strength of the Se...O inter­action also correlates with the carbonyl C=O bond length. Weak inter­molecular Se...Se, Se...O, C—H...O, C—H...π and π–π inter­actions each serve to link the mol­ecules into ribbons or chains, with the C—H...O motif being a double helix, while the combination of all inter­actions generates the overall three-dimensional supra­molecular framework.

Computing details

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1991); cell refinement: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1991); data reduction: TEXSAN (Molecular Structure Corporation, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2013); molecular graphics: ORTEPII (Johnson, 1976) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2013 (Sheldrick, 2013), publCIF (Westrip, 2010) and PLATON (Spek, 2009)'.

N-[5-(morpholin-4-yl)-3H-1,2,4-diselenazol-3-ylidene]benzamide

Crystal data

C13H13N3O2Se2	F(000) = 784
Mr = 401.18	Dx = 1.863 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.923 (5) Å	Cell parameters from 25 reflections
b = 6.807 (4) Å	θ = 39.4–39.9°
c = 15.166 (5) Å	µ = 5.18 mm^−1
β = 95.76 (3)°	T = 160 K
V = 1430.0 (10) Å^3	Prism, orange-yellow
Z = 4	0.50 × 0.42 × 0.17 mm

Data collection

Rigaku AFC-5R diffractometer	2135 reflections with I > 2σ(I)
Radiation source: Rigaku rotating anode generator	Rint = 0.023
Graphite monochromator	θmax = 27.5°, θmin = 2.7°
ω/2θ scans	h = 0→18
Absorption correction: ψ scan (North et al., 1968)	k = 0→8
Tmin = 0.183, Tmax = 0.415	l = −19→19
3406 measured reflections	3 standard reflections every 150 reflections
3275 independent reflections	intensity decay: none

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.038	H-atom parameters constrained
wR(F^2) = 0.092	w = 1/[σ^2(Fo^2) + (0.0358P)^2 + 0.7378P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.001
3275 reflections	Δρmax = 0.60 e Å^−3
181 parameters	Δρmin = −0.47 e Å^−3

Special details

Experimental. Solvent used: EtOH

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Se1	0.41226 (3)	0.77208 (7)	0.27089 (3)	0.03025 (14)
Se2	0.35195 (3)	1.02891 (7)	0.17399 (3)	0.03072 (14)
O1	0.4278 (2)	0.5025 (5)	0.3629 (2)	0.0355 (8)
O2	−0.0084 (3)	1.2703 (6)	0.0983 (3)	0.0597 (12)
N1	0.2661 (3)	0.5080 (5)	0.3114 (2)	0.0260 (8)
N2	0.2102 (3)	0.7635 (6)	0.2209 (2)	0.0255 (8)
N3	0.1511 (3)	1.0215 (6)	0.1360 (3)	0.0318 (9)
C1	0.3447 (3)	0.4306 (7)	0.3593 (3)	0.0256 (10)
C2	0.2829 (3)	0.6698 (6)	0.2675 (3)	0.0235 (10)
C3	0.2257 (3)	0.9274 (7)	0.1786 (3)	0.0265 (10)
C4	0.1594 (3)	1.2028 (8)	0.0852 (3)	0.0383 (13)
H41	0.1490	1.1733	0.0210	0.046*
H42	0.2252	1.2575	0.0980	0.046*
C5	0.0866 (4)	1.3510 (8)	0.1088 (4)	0.0486 (15)
H51	0.1024	1.3934	0.1710	0.058*
H52	0.0893	1.4679	0.0703	0.058*
C6	−0.0154 (4)	1.1014 (8)	0.1531 (4)	0.0474 (15)
H61	−0.0824	1.0508	0.1456	0.057*
H62	−0.0003	1.1392	0.2160	0.057*
C7	0.0522 (3)	0.9433 (7)	0.1304 (3)	0.0307 (11)
H71	0.0494	0.8320	0.1721	0.037*
H72	0.0330	0.8946	0.0697	0.037*
C8	0.3276 (3)	0.2498 (6)	0.4102 (3)	0.0250 (10)
C9	0.2463 (3)	0.1331 (7)	0.3891 (3)	0.0284 (10)
H9	0.1993	0.1728	0.3428	0.034*
C10	0.2326 (4)	−0.0374 (7)	0.4338 (3)	0.0356 (12)
H10	0.1776	−0.1168	0.4176	0.043*
C11	0.2993 (4)	−0.0935 (8)	0.5025 (3)	0.0400 (13)
H11	0.2896	−0.2112	0.5340	0.048*
C12	0.3807 (4)	0.0205 (8)	0.5261 (3)	0.0377 (12)
H12	0.4262	−0.0190	0.5736	0.045*
C13	0.3952 (3)	0.1921 (7)	0.4799 (3)	0.0305 (11)
H13	0.4508	0.2702	0.4956	0.037*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Se1	0.0177 (2)	0.0341 (3)	0.0387 (3)	−0.0006 (2)	0.00180 (19)	0.0044 (2)
Se2	0.0211 (2)	0.0347 (3)	0.0366 (3)	−0.0040 (2)	0.0040 (2)	0.0071 (2)
O1	0.0230 (17)	0.037 (2)	0.045 (2)	0.0007 (15)	0.0002 (15)	0.0096 (16)
O2	0.026 (2)	0.045 (2)	0.110 (4)	0.0092 (18)	0.015 (2)	0.017 (2)
N1	0.024 (2)	0.021 (2)	0.033 (2)	−0.0003 (16)	0.0030 (17)	0.0031 (17)
N2	0.0198 (18)	0.030 (2)	0.027 (2)	0.0012 (17)	0.0042 (16)	0.0014 (17)
N3	0.0200 (19)	0.038 (2)	0.037 (2)	−0.0039 (18)	0.0002 (17)	0.0134 (19)
C1	0.024 (2)	0.030 (3)	0.023 (2)	0.004 (2)	0.0034 (19)	−0.002 (2)
C2	0.019 (2)	0.027 (2)	0.025 (2)	−0.0002 (18)	0.0050 (18)	−0.0047 (19)
C3	0.021 (2)	0.034 (3)	0.025 (2)	−0.003 (2)	0.0065 (19)	−0.002 (2)
C4	0.025 (3)	0.044 (3)	0.047 (3)	0.000 (2)	0.007 (2)	0.020 (3)
C5	0.039 (3)	0.031 (3)	0.078 (4)	−0.003 (2)	0.015 (3)	0.003 (3)
C6	0.034 (3)	0.050 (3)	0.062 (4)	−0.003 (3)	0.020 (3)	0.005 (3)
C7	0.019 (2)	0.040 (3)	0.033 (3)	−0.001 (2)	0.001 (2)	0.008 (2)
C8	0.025 (2)	0.029 (3)	0.021 (2)	0.006 (2)	0.0061 (18)	−0.004 (2)
C9	0.030 (3)	0.029 (2)	0.026 (2)	0.003 (2)	0.004 (2)	−0.006 (2)
C10	0.039 (3)	0.029 (3)	0.040 (3)	−0.002 (2)	0.012 (2)	−0.008 (2)
C11	0.048 (3)	0.039 (3)	0.037 (3)	0.012 (3)	0.022 (3)	0.006 (2)
C12	0.037 (3)	0.047 (3)	0.030 (3)	0.014 (3)	0.008 (2)	0.006 (2)
C13	0.026 (2)	0.035 (3)	0.032 (3)	0.007 (2)	0.006 (2)	−0.002 (2)

Geometric parameters (Å, º)

Se1—Se2	2.3818 (11)	C5—H51	0.9900
Se1—C2	1.926 (4)	C5—H52	0.9900
Se1—O1	2.302 (3)	C6—C7	1.492 (7)
Se2—C3	1.897 (4)	C6—H61	0.9900
O1—C1	1.252 (5)	C6—H62	0.9900
O2—C5	1.427 (6)	C7—H71	0.9900
O2—C6	1.428 (6)	C7—H72	0.9900
N1—C1	1.358 (6)	C8—C9	1.393 (6)
N1—C2	1.320 (5)	C8—C13	1.400 (6)
N2—C2	1.337 (5)	C9—C10	1.366 (6)
N2—C3	1.316 (6)	C9—H9	0.9500
N3—C3	1.331 (6)	C10—C11	1.378 (7)
N3—C4	1.465 (6)	C10—H10	0.9500
N3—C7	1.470 (6)	C11—C12	1.390 (8)
C1—C8	1.485 (6)	C11—H11	0.9500
C4—C5	1.499 (7)	C12—C13	1.387 (7)
C4—H41	0.9900	C12—H12	0.9500
C4—H42	0.9900	C13—H13	0.9500
Se2—Se1—O1	164.75 (8)	H51—C5—H52	108.1
Se2—Se1—C2	88.74 (14)	O2—C6—C7	111.4 (4)
O1—Se1—C2	76.05 (16)	O2—C6—H61	109.3
Se1—Se2—C3	88.90 (15)	C7—C6—H61	109.3
C1—O1—Se1	104.8 (3)	O2—C6—H62	109.3
C5—O2—C6	111.2 (4)	C7—C6—H62	109.3
C2—N1—C1	114.8 (4)	H61—C6—H62	108.0
C3—N2—C2	120.6 (4)	N3—C7—C6	109.5 (4)
C3—N3—C4	124.1 (4)	N3—C7—H71	109.8
C3—N3—C7	122.3 (4)	C6—C7—H71	109.8
C4—N3—C7	113.5 (4)	N3—C7—H72	109.8
O1—C1—N1	124.3 (4)	C6—C7—H72	109.8
O1—C1—C8	119.8 (4)	H71—C7—H72	108.2
N1—C1—C8	115.9 (4)	C9—C8—C13	118.8 (4)
N1—C2—N2	120.1 (4)	C9—C8—C1	121.5 (4)
N1—C2—Se1	120.0 (3)	C13—C8—C1	119.6 (4)
N2—C2—Se1	119.9 (3)	C10—C9—C8	121.4 (5)
N2—C3—N3	119.1 (4)	C10—C9—H9	119.3
N2—C3—Se2	121.7 (3)	C8—C9—H9	119.3
N3—C3—Se2	119.2 (3)	C9—C10—C11	119.6 (5)
N3—C4—C5	110.5 (4)	C9—C10—H10	120.2
N3—C4—H41	109.5	C11—C10—H10	120.2
C5—C4—H41	109.5	C10—C11—C12	120.6 (5)
N3—C4—H42	109.5	C10—C11—H11	119.7
C5—C4—H42	109.5	C12—C11—H11	119.7
H41—C4—H42	108.1	C13—C12—C11	119.8 (5)
O2—C5—C4	110.9 (4)	C13—C12—H12	120.1
O2—C5—H51	109.5	C11—C12—H12	120.1
C4—C5—H51	109.5	C12—C13—C8	119.8 (5)
O2—C5—H52	109.5	C12—C13—H13	120.1
C4—C5—H52	109.5	C8—C13—H13	120.1
Se1—O1—C1—N1	−1.4 (5)	C6—O2—C5—C4	59.3 (6)
Se1—O1—C1—C8	178.9 (3)	N3—C4—C5—O2	−54.2 (6)
C2—N1—C1—O1	−0.3 (6)	C5—O2—C6—C7	−60.4 (6)
C2—N1—C1—C8	179.3 (4)	C3—N3—C7—C6	132.3 (5)
C1—N1—C2—N2	−177.3 (4)	C4—N3—C7—C6	−51.9 (5)
C1—N1—C2—Se1	2.5 (5)	O2—C6—C7—N3	55.4 (6)
C3—N2—C2—N1	178.4 (4)	O1—C1—C8—C9	−160.8 (4)
C3—N2—C2—Se1	−1.3 (5)	N1—C1—C8—C9	19.5 (6)
C2—N2—C3—N3	−177.1 (4)	O1—C1—C8—C13	18.0 (6)
C2—N2—C3—Se2	4.7 (6)	N1—C1—C8—C13	−161.7 (4)
C4—N3—C3—N2	−178.8 (4)	C13—C8—C9—C10	−1.4 (6)
C7—N3—C3—N2	−3.3 (7)	C1—C8—C9—C10	177.4 (4)
C4—N3—C3—Se2	−0.5 (6)	C8—C9—C10—C11	1.5 (7)
C7—N3—C3—Se2	174.9 (3)	C9—C10—C11—C12	−0.7 (7)
Se1—Se2—C3—N2	−4.6 (4)	C10—C11—C12—C13	−0.2 (7)
Se1—Se2—C3—N3	177.2 (4)	C11—C12—C13—C8	0.3 (7)
C3—N3—C4—C5	−132.6 (5)	C9—C8—C13—C12	0.5 (6)
C7—N3—C4—C5	51.6 (6)	C1—C8—C13—C12	−178.3 (4)