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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229614008237/ky3053sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229614008237/ky3053Isup2.hkl
Contains datablock I

cdx

Chemdraw file https://doi.org/10.1107/S2053229614008237/ky3053Isup3.cdx
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229614008237/ky3053Isup4.cml
Supplementary material

CCDC reference: 996895

Computing details top

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 top
Crystal data top
C13H13N3O2Se2F(000) = 784
Mr = 401.18Dx = 1.863 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 13.923 (5) ÅCell parameters from 25 reflections
b = 6.807 (4) Åθ = 39.4–39.9°
c = 15.166 (5) ŵ = 5.18 mm1
β = 95.76 (3)°T = 160 K
V = 1430.0 (10) Å3Prism, orange-yellow
Z = 40.50 × 0.42 × 0.17 mm
Data collection top
Rigaku AFC-5R
diffractometer
2135 reflections with I > 2σ(I)
Radiation source: Rigaku rotating anode generatorRint = 0.023
Graphite monochromatorθmax = 27.5°, θmin = 2.7°
ω/2θ scansh = 018
Absorption correction: ψ scan
(North et al., 1968)
k = 08
Tmin = 0.183, Tmax = 0.415l = 1919
3406 measured reflections3 standard reflections every 150 reflections
3275 independent reflections intensity decay: none
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.038H-atom parameters constrained
wR(F2) = 0.092 w = 1/[σ2(Fo2) + (0.0358P)2 + 0.7378P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.001
3275 reflectionsΔρmax = 0.60 e Å3
181 parametersΔρmin = 0.47 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
Se10.41226 (3)0.77208 (7)0.27089 (3)0.03025 (14)
Se20.35195 (3)1.02891 (7)0.17399 (3)0.03072 (14)
O10.4278 (2)0.5025 (5)0.3629 (2)0.0355 (8)
O20.0084 (3)1.2703 (6)0.0983 (3)0.0597 (12)
N10.2661 (3)0.5080 (5)0.3114 (2)0.0260 (8)
N20.2102 (3)0.7635 (6)0.2209 (2)0.0255 (8)
N30.1511 (3)1.0215 (6)0.1360 (3)0.0318 (9)
C10.3447 (3)0.4306 (7)0.3593 (3)0.0256 (10)
C20.2829 (3)0.6698 (6)0.2675 (3)0.0235 (10)
C30.2257 (3)0.9274 (7)0.1786 (3)0.0265 (10)
C40.1594 (3)1.2028 (8)0.0852 (3)0.0383 (13)
H410.14901.17330.02100.046*
H420.22521.25750.09800.046*
C50.0866 (4)1.3510 (8)0.1088 (4)0.0486 (15)
H510.10241.39340.17100.058*
H520.08931.46790.07030.058*
C60.0154 (4)1.1014 (8)0.1531 (4)0.0474 (15)
H610.08241.05080.14560.057*
H620.00031.13920.21600.057*
C70.0522 (3)0.9433 (7)0.1304 (3)0.0307 (11)
H710.04940.83200.17210.037*
H720.03300.89460.06970.037*
C80.3276 (3)0.2498 (6)0.4102 (3)0.0250 (10)
C90.2463 (3)0.1331 (7)0.3891 (3)0.0284 (10)
H90.19930.17280.34280.034*
C100.2326 (4)0.0374 (7)0.4338 (3)0.0356 (12)
H100.17760.11680.41760.043*
C110.2993 (4)0.0935 (8)0.5025 (3)0.0400 (13)
H110.28960.21120.53400.048*
C120.3807 (4)0.0205 (8)0.5261 (3)0.0377 (12)
H120.42620.01900.57360.045*
C130.3952 (3)0.1921 (7)0.4799 (3)0.0305 (11)
H130.45080.27020.49560.037*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Se10.0177 (2)0.0341 (3)0.0387 (3)0.0006 (2)0.00180 (19)0.0044 (2)
Se20.0211 (2)0.0347 (3)0.0366 (3)0.0040 (2)0.0040 (2)0.0071 (2)
O10.0230 (17)0.037 (2)0.045 (2)0.0007 (15)0.0002 (15)0.0096 (16)
O20.026 (2)0.045 (2)0.110 (4)0.0092 (18)0.015 (2)0.017 (2)
N10.024 (2)0.021 (2)0.033 (2)0.0003 (16)0.0030 (17)0.0031 (17)
N20.0198 (18)0.030 (2)0.027 (2)0.0012 (17)0.0042 (16)0.0014 (17)
N30.0200 (19)0.038 (2)0.037 (2)0.0039 (18)0.0002 (17)0.0134 (19)
C10.024 (2)0.030 (3)0.023 (2)0.004 (2)0.0034 (19)0.002 (2)
C20.019 (2)0.027 (2)0.025 (2)0.0002 (18)0.0050 (18)0.0047 (19)
C30.021 (2)0.034 (3)0.025 (2)0.003 (2)0.0065 (19)0.002 (2)
C40.025 (3)0.044 (3)0.047 (3)0.000 (2)0.007 (2)0.020 (3)
C50.039 (3)0.031 (3)0.078 (4)0.003 (2)0.015 (3)0.003 (3)
C60.034 (3)0.050 (3)0.062 (4)0.003 (3)0.020 (3)0.005 (3)
C70.019 (2)0.040 (3)0.033 (3)0.001 (2)0.001 (2)0.008 (2)
C80.025 (2)0.029 (3)0.021 (2)0.006 (2)0.0061 (18)0.004 (2)
C90.030 (3)0.029 (2)0.026 (2)0.003 (2)0.004 (2)0.006 (2)
C100.039 (3)0.029 (3)0.040 (3)0.002 (2)0.012 (2)0.008 (2)
C110.048 (3)0.039 (3)0.037 (3)0.012 (3)0.022 (3)0.006 (2)
C120.037 (3)0.047 (3)0.030 (3)0.014 (3)0.008 (2)0.006 (2)
C130.026 (2)0.035 (3)0.032 (3)0.007 (2)0.006 (2)0.002 (2)
Geometric parameters (Å, º) top
Se1—Se22.3818 (11)C5—H510.9900
Se1—C21.926 (4)C5—H520.9900
Se1—O12.302 (3)C6—C71.492 (7)
Se2—C31.897 (4)C6—H610.9900
O1—C11.252 (5)C6—H620.9900
O2—C51.427 (6)C7—H710.9900
O2—C61.428 (6)C7—H720.9900
N1—C11.358 (6)C8—C91.393 (6)
N1—C21.320 (5)C8—C131.400 (6)
N2—C21.337 (5)C9—C101.366 (6)
N2—C31.316 (6)C9—H90.9500
N3—C31.331 (6)C10—C111.378 (7)
N3—C41.465 (6)C10—H100.9500
N3—C71.470 (6)C11—C121.390 (8)
C1—C81.485 (6)C11—H110.9500
C4—C51.499 (7)C12—C131.387 (7)
C4—H410.9900C12—H120.9500
C4—H420.9900C13—H130.9500
Se2—Se1—O1164.75 (8)H51—C5—H52108.1
Se2—Se1—C288.74 (14)O2—C6—C7111.4 (4)
O1—Se1—C276.05 (16)O2—C6—H61109.3
Se1—Se2—C388.90 (15)C7—C6—H61109.3
C1—O1—Se1104.8 (3)O2—C6—H62109.3
C5—O2—C6111.2 (4)C7—C6—H62109.3
C2—N1—C1114.8 (4)H61—C6—H62108.0
C3—N2—C2120.6 (4)N3—C7—C6109.5 (4)
C3—N3—C4124.1 (4)N3—C7—H71109.8
C3—N3—C7122.3 (4)C6—C7—H71109.8
C4—N3—C7113.5 (4)N3—C7—H72109.8
O1—C1—N1124.3 (4)C6—C7—H72109.8
O1—C1—C8119.8 (4)H71—C7—H72108.2
N1—C1—C8115.9 (4)C9—C8—C13118.8 (4)
N1—C2—N2120.1 (4)C9—C8—C1121.5 (4)
N1—C2—Se1120.0 (3)C13—C8—C1119.6 (4)
N2—C2—Se1119.9 (3)C10—C9—C8121.4 (5)
N2—C3—N3119.1 (4)C10—C9—H9119.3
N2—C3—Se2121.7 (3)C8—C9—H9119.3
N3—C3—Se2119.2 (3)C9—C10—C11119.6 (5)
N3—C4—C5110.5 (4)C9—C10—H10120.2
N3—C4—H41109.5C11—C10—H10120.2
C5—C4—H41109.5C10—C11—C12120.6 (5)
N3—C4—H42109.5C10—C11—H11119.7
C5—C4—H42109.5C12—C11—H11119.7
H41—C4—H42108.1C13—C12—C11119.8 (5)
O2—C5—C4110.9 (4)C13—C12—H12120.1
O2—C5—H51109.5C11—C12—H12120.1
C4—C5—H51109.5C12—C13—C8119.8 (5)
O2—C5—H52109.5C12—C13—H13120.1
C4—C5—H52109.5C8—C13—H13120.1
Se1—O1—C1—N11.4 (5)C6—O2—C5—C459.3 (6)
Se1—O1—C1—C8178.9 (3)N3—C4—C5—O254.2 (6)
C2—N1—C1—O10.3 (6)C5—O2—C6—C760.4 (6)
C2—N1—C1—C8179.3 (4)C3—N3—C7—C6132.3 (5)
C1—N1—C2—N2177.3 (4)C4—N3—C7—C651.9 (5)
C1—N1—C2—Se12.5 (5)O2—C6—C7—N355.4 (6)
C3—N2—C2—N1178.4 (4)O1—C1—C8—C9160.8 (4)
C3—N2—C2—Se11.3 (5)N1—C1—C8—C919.5 (6)
C2—N2—C3—N3177.1 (4)O1—C1—C8—C1318.0 (6)
C2—N2—C3—Se24.7 (6)N1—C1—C8—C13161.7 (4)
C4—N3—C3—N2178.8 (4)C13—C8—C9—C101.4 (6)
C7—N3—C3—N23.3 (7)C1—C8—C9—C10177.4 (4)
C4—N3—C3—Se20.5 (6)C8—C9—C10—C111.5 (7)
C7—N3—C3—Se2174.9 (3)C9—C10—C11—C120.7 (7)
Se1—Se2—C3—N24.6 (4)C10—C11—C12—C130.2 (7)
Se1—Se2—C3—N3177.2 (4)C11—C12—C13—C80.3 (7)
C3—N3—C4—C5132.6 (5)C9—C8—C13—C120.5 (6)
C7—N3—C4—C551.6 (6)C1—C8—C13—C12178.3 (4)
 

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