2,5-Diaryl-1,3,4-selenadiazo­les prepared from Woollins' reagent

Two polymorphs of 2,5-diphenyl-1,3,4-selenadiazole, C₁₄H₁₀N₂Se, denoted (Ia) and (Ib), and a new polymorph of 2,5-bis­(thio­phen-2-yl)-1,3,4-selenadiazole, C₁₀H₆N₂S₂Se, (IIb), form on crystallization of the compounds, prepared using Woollins' reagent (2,4-diphenyl-1,3-diselenadiphosphetane 2,4-diselenide). These compounds, along with 2-(4-chloro­phen­yl)-5-phenyl-1,3,4-selenadiazole, C₁₄H₉ClN₂Se, (III), and 2-(furan-2-yl)-5-(p-tol­yl)-1,3,4-selenadiazole, C₁₃H₁₀N₂OSe, (IV), show similar inter­molecular inter­actions, with π–π stacking, C—H...π inter­actions and weak hydrogen bonds typically giving rise to mol­ecular chains. However, the combination of inter­actions differs in each case, giving rise to different packing arrangements. In polymorph (Ib), the mol­ecule lies across a crystallographic twofold rotation axis, and (IV) has two independent mol­ecules in the asymmetric unit.

S1. Comment

Interest in using organoselenium heterocycles as compounds with novel properties has expanded rapidly during the last three decades. This interest has focused on areas as diverse as pharmaceutically interesting compounds (Klayman & Gunther 1973; Mugesh et al., 2001; Nicolaou & Petasis, 1984) and new reagents with unusual reactivity profiles (Back, 2000; Wirth, 2000a,b). The selenation reagent 2,4-diphenyl-1,3-diselenadiphosphetane 2,4-diselenide, [PhP(Se)(µ-Se)]₂, Woollins' reagent, is the selenium counterpart of the well known Lawesson's reagent. It has been shown to insert selenium into a wide range of different compounds, including in the formation of the title 2,5-diaryl-1,3,4-selenadiazoles (for examples, see Hua et al., 2009; Hua, Cordes et al. 2011; Hua, Griffin et al., 2011, and references therein). Five crystal structures have been determined for four selenadiazoles, two of which are polymorphs of each other, and another of which is a polymorph of a known structure; these are 2,5-diphenyl-1,3,4-selenadiazole, (Ia) (Fig. 1) and (Ib) (Fig. 2), 2,5-bis(thiophen-2-yl)-1,3,4-selenadiazole, (IIb) (Fig. 3), 2-(4-chlorophenyl)-5-phenyl-1,3,4-selenadiazole, (III) (Fig. 4), and 2-(furan-2-yl)-5-(p-tolyl)-1,3,4-selenadiazole, (IV) (Fig. 5). All five compounds were prepared according to published methods (Hua et al., 2009; Hua, Cordes et al., 2011), and crystals were grown in each case by the diffusion of hexane into a dichloromethane solution of the compound.

Three of the five structures have a single molecule of the compound in the asymmetric unit, the exceptions being polymorph (Ib) and compound (IV). In (Ib), the asymmetric unit comprises half a molecule of 2,5-diphenyl-1,3,4-selenadiazole, the other half being generated by twofold rotational symmetry, whereas in (IV), two independent molecules of 2-(furan-2-yl)-5-(p-tolyl)-1,3,4-selenadiazole form the asymmetric unit. The C—Se bond distances in (I)–(IV) vary from 1.861 (7) to 1.890 (4) Å, falling within the range of C—Se bond lengths (1.86–1.90 Å) seen in selenadiazoles (Hua et al., 2009; Hua, Cordes et al., 2011). These distances are shorter than would be expected for a C—Se single bond (ca 1.94 Å), indicating that some degree of delocalization occurs. Four of the five structures [excluding (Ib)] show the same near-planar molecular arrangement seen in previous selenadiazole structures (Hua et al., 2009; Hua, Cordes et al., 2011). The dihedral angles between peripheral ring planes and the selenadiazole rings range from 1.7 (4) to 13.5 (3)°, with the exception of polymorph (Ib), where the dihedral angle is 22.3 (2)°. Due to its rotational symmetry, this leads to the planes of its phenyl rings being inclined at 43.44 (17)° with respect to each other.

The predominant types of intermolecular interactions in these compounds are those involving their π-systems. All five of the structures show π–π stacking interactions, at a variety of centroid–centroid (Cg···Cg) distances. While some of these, with Cg···Cg distances in the range 3.6197 (19)–3.670 (4) Å, fall within the conventional range for π–π interactions, some show apparent π-stacking at distances as long as 3.930 (3) Å (Table 3). While π-interactions at such distances would conventionally be considered insignificant, in these cases the interactions are supported by acting in parallel with other interactions, including other π–π interactions and also C—H···π interactions (see below). All of the compounds, except for (IIb), also show C—H···π interactions, with C—H···Cg distances ranging from 2.52 to 2.97 Å (Table 4). While these longer distances would give rise to very weak interactions, due to their occurring at the conventional van der Waals limit, C—H···π interactions have been suggested to be effective at distances beyond this value (Nishio, 2004). In polymorph (Ib) and in (IV), these interactions occur in conjunction with π–π interactions, mutually reinforcing each other, as in these two compounds there is either sufficient angularity between the phenyl and selenadiazole rings [in (Ib)] or the presence of the tolyl methyl group [in (IV)] to allow for both C—H···π and π–π interactions between the same adjacent molecules. Further intramolecular interactions occur in (IIb) and (IV), where weak C—H···N hydrogen bonds contribute to the observed packing motif. These occur at H···N distances of 2.59 Å in (IIb), and 2.50 and 2.59 Å in (IV), with C···N separations of 3.539 (12), 3.422 (7) and 3.457 (8) Å, respectively.

While this similarity of molecular geometries and types of intramolecular interactions might suggest that similar packing modes would be observed, this is not found to be the case. The intermolecular interactions observed, namely π–π interactions, C—H···π interactions and weak C—H···N hydrogen bonds, combine in different ways, giving rise to a variety of packing motifs. In (Ia) (Fig. 6), chains formed by C—H···π interactions run along the b axis. These interact with adjacent chains by the formation of π-stacked dimers, giving rise to sheets in the (100) plane. In the cases of (Ib) (Fig. 6) and (IIb) (Fig. 7), both display two-dimensional sheets formed by the interaction of two different types of chains. Both show π-stacked chains, running along c in (Ib) and along b in (IIb), but the second type of chain is formed by C—H···π interactions along the c axis in (Ib), and by weak hydrogen bonds along the a axis in (IIb), and the resulting sheets occur in the (100) and (001) planes, respectively. The situation in (III) and (IV) is somewhat different, as each comprises a three-dimensional network formed by the linking together of two-dimensional sheets. In (III), two-dimensional sheets are formed in the (001) plane by C—H···π interactions (Fig. 8), whereas in (IV), sheets in the (100) plane are formed by a combination of C–H···π and π–π interactions, and C—H···N hydrogen bonding (Fig. 9). In both compounds, these sheets are then linked together into a three-dimensional network by the formation of π-stacked dimers between sheets.

For 2,5-diphenyl-1,3,4-selenadiazole, (I), two visually similar types of polymorphic crystals form under the same conditions. Both of these display a monoclinic unit cell, with polymorph (Ia) crystallizing in the space group P2₁/c and polymorph (Ib) in space group C2/c. On a molecular level, there is one key structural difference between the two forms, which appears to give rise to many of the differences observed in packing. This is the difference in the dihedral angles between the phenyl rings and the selenadiazole ring, with polymorph (Ia) showing angles of 3.35 (16) and 4.11 (16)°, whereas polymorph (Ib) shows a single dihedral angle of 22.3 (2)°. These differences can be seen to lead directly to differences in packing (Fig. 6), as the twist of the phenyl rings changes both the distance and angle possible for π–π interactions, inducing a molecular offset from the chain axis in (Ib), and also makes it possible for both π–π and C—H···π interactions to occur in the same molecular chain.

In the case of (IIb), the crystals appeared to be slightly visually different to those previously found for (IIa) (Hua, Cordes et al., 2011), and structure analysis revealed it to be a polymorphic form. Polymorph (IIb) crystallizes in the orthorhombic space group Pca2₁, although with broadly similar unit-cell parameters to the known structure, which crystallizes in the monoclinic space group P2₁/c. There is little on a gross structural level to indicate why a different polymorphic form occurs, a fit of all non-H atoms of polymorph (IIb) to those of polymorph (IIa) having an r.m.s. deviation of 0.052 Å. Additionally, there are similarities in the packing of the two polymorphs, but the differences between them do become more apparent as the interactions which give rise to the packing are considered. Both polymorphs display π-stacked chains running along the b axis, but these are assembled differently. In (IIb), the π-overlaps occur between the selenadiazole ring and both thiophene rings, whereas in (IIa), two different sets of π-interactions give rise to a more zigzag chain. Furthermore, (IIb) also shows chains running along the a axis formed by weak C—H···N? hydrogen bonding, the combination of these two sets of interactions giving rise to sheets in the (001) plane, while (IIa) shows no other intermolecular interactions.

Related literature

For related literature, see: Back (2000); Flack (1983); Hua et al. (2009); Hua, Cordes, Li, Slawin & Woollins (2011); Hua, Griffin, Ashbrook, Slawin & Woollins (2011); Klayman & Gunther (1973); Mugesh et al. (2001); Nicolaou & Petasis (1984); Nishio (2004); Wirth (2000a, 2000b).

S2. Experimental

All compounds were prepared according to literature methods by the reaction of Woollins' reagent with either the appropriate 1,2-diacylhydrazine [for (Ia), (Ib), (III) and (IV); Hua et al., 2009] or acylcarbohydrazide [for (IIb); Hua, Cordes et al., 2011]. X-ray quality crystals of all compounds were grown by the diffusion of hexane into a dichloromethane solution of the compound. Crystals of the two polymorphic forms of 2,5-diphenyl-1,3,4-selenadiazole, (Ia) and (Ib), were difficult to differentiate visually, except that the platelets of (Ia) tended to be thicker than those of (Ib). Crystals of (IIb) were likewise difficult to differentiate from those of the known polymorph (IIa) (Hua, Cordes et al., 2011), although those of (IIb) did tend to display a more intense orange colour.

S3. Refinement

C-bound H atoms were included in calculated positions (C—H = 0.98 Å for methyl H atoms and 0.95 Å for aryl H atoms) and refined as riding, with U_iso(H) = 1.2U_eq(C) for aryl H or 1.5U_eq(C) for methyl H. The structure of (IIb) shows signs of racemic twinning, the Flack (1983) parameter being 0.377 (19). This is complicated by the Friedel-pair coverage being lower than ideal, at 68%, which suggests that the Flack parameter in this case may be less meaningful than generally. In (III), a difference electron-density feature of 4.87 e %A^-3 was located 1.37 Å from atom Se1, but this has no chemical significance.

Computing details

For all compounds, data collection: CrystalClear (Rigaku, 2010); cell refinement: CrystalClear (Rigaku, 2010); data reduction: CrystalClear (Rigaku, 2010); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008). Molecular graphics: SHELXTL (Sheldrick, 2008) and OLEX (Dolomanov et al., 2003) for (Ia), (Ib), (IIb); SHELXTL (Sheldrick, 2008) and OLEX2 (Dolomanov et al., 2003) for (III), (IV). For all compounds, software used to prepare material for publication: SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Figures

	Fig. 1. The structure of polymorph (Ia), with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. The structure of polymorph (Ib), with displacement ellipsoids drawn at the 50% probability level. Only the asymmetric unit of the structure is labelled (symmetry code to generate the rest of the molecule: -x, y, -z + 3/2).
	Fig. 3. The structure of polymorph (IIb), with displacement ellipsoids drawn at the 50% probability level.
	Fig. 4. The structure of (III), with displacement ellipsoids drawn at the 50% probability level.
	Fig. 5. The structure of (IV), with displacement ellipsoids drawn at the 50% probability level.
	Fig. 6. Views of the different two-dimensional sheets in the (100) plane formed by the two polymorphs of (I). C—H···π interactions are shown as thin lines and H atoms not involved in these interactions have been omitted. (a) In polymorph (Ia), chains running along the b axis, formed by C—H···π interactions, are linked together by the formation of π-stacked dimers. (b) In polymorph (Ib), two sets of chains, both running along the c-axis, one formed by π-stacking and C—H···π interactions and the other by different C—H···π interactions, are mutually interconnected.
	Fig. 7. A view of the two-dimensional sheet in the (001) plane, formed by the combination of C—H···N hydrogen bonding and π-stacking, in (IIb). C—H···N hydrogen bonds are shown as thin lines and H atoms not involved in these interactions have been omitted.
	Fig. 8. Views of the three-dimensional network which makes up the structure of (III). C—H···π interactions are shown as thin lines and H atoms not involved in these interactions have been omitted. (a) The two-dimensional sheet lying in the (001) plane, formed by two sets of C—H···π interactions. (b) Two adjacent sheets, showing the π-stacking which connects them into a three-dimensional network.
	Fig. 9. Views of the three-dimensional network which makes up the structure of (IV). C—H···π and C—H···N interactions are shown as thin lines and H atoms not involved in these interactions have been omitted. (a) The two-dimensional sheet lying in the (100) plane, formed by the combination of both π-stacking and C—H···π interactions and C—H···N hydrogen bonds. (b) Two adjacent sheets, showing the π-stacking which connects them into a three-dimensional network.

(Ia) 2,5-diphenyl-1,3,4-selenadiazole

Crystal data

C14H10N2Se	F(000) = 568
Mr = 285.20	Dx = 1.670 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3915 reflections
a = 13.036 (4) Å	θ = 1.6–28.4°
b = 5.4650 (14) Å	µ = 3.29 mm^−1
c = 16.274 (5) Å	T = 93 K
β = 101.860 (7)°	Platelet, colourless
V = 1134.6 (5) Å^3	0.15 × 0.10 × 0.05 mm
Z = 4

Data collection

Rigaku Mercury CCD area-detector diffractometer	2413 independent reflections
Radiation source: rotating anode	2081 reflections with I > 2σ(I)
Confocal monochromator	Rint = 0.037
Detector resolution: 14.7059 pixels mm^-1	θmax = 28.6°, θmin = 1.6°
ω and ϕ scans	h = −16→15
Absorption correction: multi-scan (CrystalClear; Rigaku, 2010)	k = −7→5
Tmin = 0.795, Tmax = 1.000	l = −16→21
7425 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.041	H-atom parameters constrained
wR(F^2) = 0.081	w = 1/[σ^2(Fo^2) + (0.0205P)^2 + 1.2418P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max < 0.001
2413 reflections	Δρmax = 1.25 e Å^−3
155 parameters	Δρmin = −0.69 e Å^−3
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0024 (6)

Special details

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	0.91133 (2)	0.13109 (5)	0.293061 (16)	0.02068 (14)
N4	0.82019 (19)	−0.2835 (4)	0.33044 (14)	0.0249 (6)
N3	0.91878 (19)	−0.2871 (4)	0.38062 (14)	0.0234 (5)
C5	0.7995 (2)	−0.0927 (5)	0.28210 (17)	0.0202 (6)
C21	0.6975 (2)	−0.0548 (5)	0.22543 (16)	0.0205 (6)
C26	0.6179 (2)	−0.2262 (5)	0.22610 (18)	0.0240 (6)
H26	0.6304	−0.3625	0.2630	0.029*
C25	0.5210 (2)	−0.1981 (6)	0.17321 (18)	0.0278 (7)
H25	0.4672	−0.3146	0.1744	0.033*
C24	0.5015 (2)	−0.0003 (5)	0.11811 (18)	0.0268 (7)
H24	0.4353	0.0173	0.0811	0.032*
C23	0.5801 (2)	0.1705 (5)	0.11809 (18)	0.0249 (7)
H23	0.5673	0.3067	0.0811	0.030*
C22	0.6772 (2)	0.1450 (5)	0.17125 (18)	0.0214 (6)
H22	0.7301	0.2641	0.1708	0.026*
C2	0.9772 (2)	−0.0997 (5)	0.37245 (16)	0.0190 (6)
C11	1.0842 (2)	−0.0686 (5)	0.42239 (16)	0.0189 (6)
C16	1.1249 (2)	−0.2410 (5)	0.48439 (17)	0.0219 (6)
H16	1.0839	−0.3790	0.4929	0.026*
C15	1.2240 (2)	−0.2115 (5)	0.53317 (18)	0.0256 (7)
H15	1.2505	−0.3285	0.5754	0.031*
C14	1.2853 (2)	−0.0119 (5)	0.52103 (17)	0.0246 (6)
H14	1.3536	0.0075	0.5546	0.029*
C13	1.2458 (2)	0.1584 (5)	0.45956 (18)	0.0247 (7)
H13	1.2873	0.2953	0.4510	0.030*
C12	1.1461 (2)	0.1305 (5)	0.41050 (17)	0.0212 (7)
H12	1.1199	0.2481	0.3685	0.025*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Se1	0.0254 (2)	0.0157 (2)	0.0217 (2)	−0.00100 (10)	0.00638 (13)	0.00346 (10)
N4	0.0303 (14)	0.0191 (13)	0.0248 (13)	−0.0005 (11)	0.0045 (10)	0.0007 (11)
N3	0.0283 (14)	0.0169 (12)	0.0258 (13)	−0.0009 (11)	0.0073 (10)	0.0017 (11)
C5	0.0266 (16)	0.0170 (14)	0.0198 (14)	−0.0018 (12)	0.0112 (12)	−0.0033 (12)
C21	0.0247 (15)	0.0188 (14)	0.0203 (13)	0.0003 (12)	0.0101 (11)	−0.0035 (12)
C26	0.0304 (17)	0.0191 (15)	0.0244 (14)	−0.0018 (13)	0.0098 (13)	−0.0004 (13)
C25	0.0308 (18)	0.0258 (16)	0.0291 (16)	−0.0045 (14)	0.0113 (13)	−0.0037 (14)
C24	0.0258 (16)	0.0292 (17)	0.0259 (15)	0.0032 (13)	0.0061 (12)	−0.0037 (13)
C23	0.0278 (17)	0.0224 (15)	0.0261 (16)	0.0065 (13)	0.0096 (13)	0.0039 (13)
C22	0.0227 (16)	0.0162 (15)	0.0278 (16)	0.0004 (11)	0.0109 (13)	0.0000 (12)
C2	0.0287 (16)	0.0146 (13)	0.0163 (13)	0.0029 (12)	0.0105 (12)	−0.0017 (11)
C11	0.0268 (15)	0.0167 (13)	0.0155 (13)	0.0037 (12)	0.0096 (11)	−0.0016 (12)
C16	0.0261 (16)	0.0178 (14)	0.0242 (14)	0.0027 (12)	0.0111 (12)	0.0033 (12)
C15	0.0320 (17)	0.0219 (16)	0.0252 (15)	0.0074 (13)	0.0111 (13)	0.0036 (13)
C14	0.0251 (16)	0.0271 (16)	0.0217 (14)	0.0002 (12)	0.0051 (12)	−0.0033 (13)
C13	0.0304 (18)	0.0229 (15)	0.0217 (15)	−0.0049 (12)	0.0077 (13)	−0.0014 (12)
C12	0.0318 (17)	0.0180 (15)	0.0146 (14)	0.0026 (12)	0.0066 (12)	0.0028 (11)

Geometric parameters (Å, º)

Se1—C2	1.882 (3)	C23—H23	0.9500
Se1—C5	1.883 (3)	C22—H22	0.9500
N4—C5	1.301 (3)	C2—C11	1.473 (4)
N4—N3	1.374 (3)	C11—C12	1.391 (4)
N3—C2	1.300 (3)	C11—C16	1.403 (4)
C5—C21	1.469 (4)	C16—C15	1.380 (4)
C21—C22	1.394 (4)	C16—H16	0.9500
C21—C26	1.400 (4)	C15—C14	1.390 (4)
C26—C25	1.383 (4)	C15—H15	0.9500
C26—H26	0.9500	C14—C13	1.386 (4)
C25—C24	1.394 (4)	C14—H14	0.9500
C25—H25	0.9500	C13—C12	1.387 (4)
C24—C23	1.386 (4)	C13—H13	0.9500
C24—H24	0.9500	C12—H12	0.9500
C23—C22	1.385 (4)
C2—Se1—C5	82.25 (12)	C21—C22—H22	119.9
C5—N4—N3	115.1 (2)	N3—C2—C11	122.9 (2)
C2—N3—N4	115.1 (2)	N3—C2—Se1	113.8 (2)
N4—C5—C21	122.8 (3)	C11—C2—Se1	123.3 (2)
N4—C5—Se1	113.8 (2)	C12—C11—C16	118.8 (3)
C21—C5—Se1	123.5 (2)	C12—C11—C2	121.6 (2)
C22—C21—C26	119.0 (3)	C16—C11—C2	119.6 (3)
C22—C21—C5	122.5 (3)	C15—C16—C11	120.4 (3)
C26—C21—C5	118.6 (3)	C15—C16—H16	119.8
C25—C26—C21	120.3 (3)	C11—C16—H16	119.8
C25—C26—H26	119.9	C16—C15—C14	120.5 (3)
C21—C26—H26	119.9	C16—C15—H15	119.7
C26—C25—C24	120.6 (3)	C14—C15—H15	119.7
C26—C25—H25	119.7	C13—C14—C15	119.4 (3)
C24—C25—H25	119.7	C13—C14—H14	120.3
C23—C24—C25	119.0 (3)	C15—C14—H14	120.3
C23—C24—H24	120.5	C14—C13—C12	120.4 (3)
C25—C24—H24	120.5	C14—C13—H13	119.8
C22—C23—C24	120.9 (3)	C12—C13—H13	119.8
C22—C23—H23	119.6	C13—C12—C11	120.5 (3)
C24—C23—H23	119.6	C13—C12—H12	119.7
C23—C22—C21	120.2 (3)	C11—C12—H12	119.7
C23—C22—H22	119.9
C5—N4—N3—C2	−0.1 (3)	N4—N3—C2—C11	178.5 (2)
N3—N4—C5—C21	−178.8 (2)	N4—N3—C2—Se1	−0.1 (3)
N3—N4—C5—Se1	0.3 (3)	C5—Se1—C2—N3	0.2 (2)
C2—Se1—C5—N4	−0.2 (2)	C5—Se1—C2—C11	−178.4 (2)
C2—Se1—C5—C21	178.8 (2)	N3—C2—C11—C12	178.1 (2)
N4—C5—C21—C22	−177.3 (3)	Se1—C2—C11—C12	−3.5 (4)
Se1—C5—C21—C22	3.8 (4)	N3—C2—C11—C16	−2.9 (4)
N4—C5—C21—C26	2.7 (4)	Se1—C2—C11—C16	175.58 (19)
Se1—C5—C21—C26	−176.2 (2)	C12—C11—C16—C15	0.7 (4)
C22—C21—C26—C25	0.5 (4)	C2—C11—C16—C15	−178.4 (2)
C5—C21—C26—C25	−179.5 (3)	C11—C16—C15—C14	−0.6 (4)
C21—C26—C25—C24	0.5 (4)	C16—C15—C14—C13	0.3 (4)
C26—C25—C24—C23	−1.1 (4)	C15—C14—C13—C12	0.0 (4)
C25—C24—C23—C22	0.6 (4)	C14—C13—C12—C11	0.1 (4)
C24—C23—C22—C21	0.5 (4)	C16—C11—C12—C13	−0.5 (4)
C26—C21—C22—C23	−1.0 (4)	C2—C11—C12—C13	178.6 (2)
C5—C21—C22—C23	179.0 (3)

(Ib) 2,5-diphenyl-1,3,4-selenadiazole

Crystal data

C14H10N2Se	F(000) = 568
Mr = 285.20	Dx = 1.744 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1743 reflections
a = 26.763 (10) Å	θ = 1.6–28.5°
b = 5.796 (2) Å	µ = 3.43 mm^−1
c = 7.213 (3) Å	T = 93 K
β = 103.885 (9)°	Platelet, colourless
V = 1086.2 (7) Å^3	0.25 × 0.20 × 0.01 mm
Z = 4

Data collection

Rigaku Mercury CCD area-detector diffractometer	1149 independent reflections
Radiation source: rotating anode	1014 reflections with I > 2σ(I)
Confocal monochromator	Rint = 0.053
Detector resolution: 14.7059 pixels mm^-1	θmax = 28.5°, θmin = 1.6°
ω and ϕ scans	h = −29→33
Absorption correction: multi-scan (CrystalClear; Rigaku, 2010)	k = −7→6
Tmin = 0.490, Tmax = 1.000	l = −8→8
3541 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.167	H-atom parameters constrained
S = 1.11	w = 1/[σ^2(Fo^2) + (0.0732P)^2 + 8.2817P] where P = (Fo^2 + 2Fc^2)/3
1149 reflections	(Δ/σ)max < 0.001
78 parameters	Δρmax = 0.92 e Å^−3
0 restraints	Δρmin = −1.14 e Å^−3

Special details

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	0.0000	0.10447 (14)	0.7500	0.0302 (4)
N3	0.02554 (18)	0.5566 (9)	0.7995 (7)	0.0261 (11)
C2	0.0449 (2)	0.3517 (10)	0.8391 (8)	0.0255 (12)
C11	0.0984 (2)	0.3062 (10)	0.9412 (8)	0.0251 (12)
C16	0.1360 (2)	0.4744 (11)	0.9475 (8)	0.0281 (13)
H16	0.1266	0.6183	0.8861	0.034*
C15	0.1858 (2)	0.4374 (11)	1.0392 (9)	0.0291 (13)
H15	0.2109	0.5536	1.0411	0.035*
C14	0.1994 (2)	0.2331 (12)	1.1283 (9)	0.0352 (15)
H14	0.2343	0.2080	1.1926	0.042*
C13	0.1646 (2)	0.0640 (11)	1.1282 (9)	0.0303 (13)
H13	0.1751	−0.0770	1.1931	0.036*
C12	0.1135 (2)	0.0974 (9)	1.0329 (9)	0.0269 (13)
H12	0.0890	−0.0217	1.0302	0.032*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Se1	0.0308 (6)	0.0250 (5)	0.0327 (6)	0.000	0.0036 (4)	0.000
N3	0.024 (3)	0.028 (3)	0.025 (3)	0.0012 (19)	0.0025 (19)	0.000 (2)
C2	0.022 (3)	0.032 (3)	0.022 (3)	−0.001 (2)	0.004 (2)	−0.003 (2)
C11	0.028 (3)	0.021 (3)	0.029 (3)	0.000 (2)	0.013 (2)	−0.001 (2)
C16	0.032 (3)	0.024 (3)	0.028 (3)	−0.003 (2)	0.008 (2)	0.001 (3)
C15	0.021 (3)	0.032 (3)	0.034 (3)	−0.006 (2)	0.005 (2)	0.003 (3)
C14	0.027 (3)	0.039 (4)	0.039 (4)	0.004 (3)	0.006 (3)	−0.001 (3)
C13	0.036 (4)	0.029 (3)	0.026 (3)	0.007 (3)	0.008 (3)	0.003 (3)
C12	0.029 (3)	0.023 (3)	0.029 (3)	0.000 (2)	0.009 (2)	0.001 (2)

Geometric parameters (Å, º)

Se1—C2	1.881 (6)	C16—H16	0.9500
Se1—C2^i	1.881 (6)	C15—C14	1.355 (9)
N3—C2	1.300 (7)	C15—H15	0.9500
N3—N3^i	1.382 (9)	C14—C13	1.352 (9)
C2—C11	1.470 (8)	C14—H14	0.9500
C11—C12	1.392 (8)	C13—C12	1.389 (9)
C11—C16	1.394 (8)	C13—H13	0.9500
C16—C15	1.354 (8)	C12—H12	0.9500
C2—Se1—C2^i	80.7 (4)	C16—C15—H15	120.3
C2—N3—N3^i	113.9 (3)	C14—C15—H15	120.3
N3—C2—C11	124.2 (5)	C13—C14—C15	121.8 (6)
N3—C2—Se1	115.7 (4)	C13—C14—H14	119.1
C11—C2—Se1	120.0 (4)	C15—C14—H14	119.1
C12—C11—C16	117.9 (5)	C14—C13—C12	119.7 (6)
C12—C11—C2	122.1 (5)	C14—C13—H13	120.2
C16—C11—C2	120.0 (5)	C12—C13—H13	120.2
C15—C16—C11	121.5 (6)	C13—C12—C11	119.7 (6)
C15—C16—H16	119.3	C13—C12—H12	120.1
C11—C16—H16	119.3	C11—C12—H12	120.1
C16—C15—C14	119.4 (6)
N3^i—N3—C2—C11	179.3 (5)	C12—C11—C16—C15	0.1 (9)
N3^i—N3—C2—Se1	1.1 (8)	C2—C11—C16—C15	−179.5 (5)
C2^i—Se1—C2—N3	−0.4 (3)	C11—C16—C15—C14	−0.5 (9)
C2^i—Se1—C2—C11	−178.7 (6)	C16—C15—C14—C13	0.1 (10)
N3—C2—C11—C12	159.3 (6)	C15—C14—C13—C12	0.8 (10)
Se1—C2—C11—C12	−22.6 (7)	C14—C13—C12—C11	−1.2 (9)
N3—C2—C11—C16	−21.1 (9)	C16—C11—C12—C13	0.7 (8)
Se1—C2—C11—C16	157.0 (5)	C2—C11—C12—C13	−179.7 (5)

Symmetry code: (i) −x, y, −z+3/2.

(IIb) 2,5-bis(thiophen-2-yl)-1,3,4-selenadiazole

Crystal data

C10H6N2S2Se	F(000) = 584
Mr = 297.25	Dx = 1.892 Mg m^−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 3222 reflections
a = 10.641 (5) Å	θ = 3.8–28.6°
b = 5.134 (2) Å	µ = 3.96 mm^−1
c = 19.096 (8) Å	T = 93 K
V = 1043.4 (7) Å^3	Block, orange
Z = 4	0.25 × 0.08 × 0.08 mm

Data collection

Rigaku Mercury CCD area-detector diffractometer	2060 independent reflections
Radiation source: rotating anode	1704 reflections with I > 2σ(I)
Confocal monochromator	Rint = 0.083
Detector resolution: 14.7059 pixels mm^-1	θmax = 28.6°, θmin = 2.1°
ω and ϕ scans	h = −13→12
Absorption correction: multi-scan (CrystalClear; Rigaku, 2010)	k = −5→6
Tmin = 0.551, Tmax = 1.000	l = −20→23
6487 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.054	w = 1/[σ^2(Fo^2) + (0.0199P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.116	(Δ/σ)max = 0.001
S = 1.12	Δρmax = 1.08 e Å^−3
2060 reflections	Δρmin = −0.67 e Å^−3
138 parameters	Extinction correction: SHELXTL (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.0092 (14)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), with 874 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.377 (19)

Special details

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	0.97218 (6)	0.71715 (12)	0.90178 (5)	0.0303 (3)
S21	1.2387 (2)	0.3484 (4)	1.05778 (11)	0.0377 (5)
S11	1.1823 (2)	1.3291 (4)	0.77777 (11)	0.0400 (5)
N4	1.2154 (7)	0.7314 (12)	0.9380 (3)	0.0343 (16)
N3	1.2041 (5)	0.9148 (12)	0.8873 (3)	0.0334 (14)
C5	1.1126 (7)	0.6082 (14)	0.9529 (3)	0.0289 (16)
C22	1.1073 (7)	0.4086 (14)	1.0068 (3)	0.0296 (17)
C23	1.0089 (9)	0.2461 (13)	1.0249 (5)	0.034 (2)
H23	0.9285	0.2507	1.0033	0.041*
C24	1.0418 (7)	0.0731 (16)	1.0791 (4)	0.036 (2)
H24	0.9865	−0.0554	1.0973	0.043*
C25	1.1613 (7)	0.1097 (15)	1.1025 (4)	0.0378 (19)
H25	1.1977	0.0127	1.1397	0.045*
C2	1.0904 (6)	0.9391 (13)	0.8619 (3)	0.0283 (16)
C12	1.0652 (7)	1.1260 (14)	0.8052 (4)	0.0312 (16)
C13	0.9525 (8)	1.1754 (16)	0.7714 (4)	0.0313 (19)
H13	0.8762	1.0855	0.7806	0.038*
C14	0.9657 (7)	1.3778 (16)	0.7213 (4)	0.0339 (19)
H14	0.8988	1.4387	0.6927	0.041*
C15	1.0837 (7)	1.4747 (15)	0.7185 (4)	0.044 (2)
H15	1.1091	1.6085	0.6872	0.052*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Se1	0.0280 (5)	0.0308 (4)	0.0323 (4)	0.0002 (3)	−0.0015 (4)	0.0017 (5)
S21	0.0356 (12)	0.0414 (13)	0.0361 (11)	−0.0013 (10)	−0.0063 (9)	0.0056 (8)
S11	0.0365 (12)	0.0356 (12)	0.0478 (13)	−0.0010 (9)	0.0022 (10)	0.0072 (9)
N4	0.030 (4)	0.034 (4)	0.039 (4)	0.003 (3)	0.000 (3)	0.001 (3)
N3	0.037 (4)	0.031 (4)	0.032 (4)	0.005 (3)	−0.007 (3)	0.004 (3)
C5	0.027 (4)	0.030 (5)	0.030 (4)	0.004 (3)	−0.002 (3)	−0.004 (3)
C22	0.029 (4)	0.035 (5)	0.025 (4)	0.004 (3)	0.003 (3)	−0.003 (3)
C23	0.033 (5)	0.031 (5)	0.039 (6)	−0.004 (3)	−0.016 (5)	−0.003 (3)
C24	0.048 (5)	0.028 (5)	0.033 (5)	−0.010 (3)	0.006 (3)	0.003 (3)
C25	0.040 (5)	0.032 (5)	0.042 (5)	−0.003 (4)	−0.002 (4)	0.003 (3)
C2	0.033 (4)	0.028 (4)	0.024 (3)	0.001 (3)	0.005 (3)	−0.006 (3)
C12	0.037 (4)	0.021 (4)	0.036 (4)	−0.002 (3)	−0.005 (4)	−0.002 (3)
C13	0.039 (5)	0.025 (4)	0.030 (5)	−0.004 (3)	0.006 (4)	−0.001 (3)
C14	0.042 (5)	0.038 (5)	0.022 (4)	0.011 (4)	−0.007 (3)	−0.002 (3)
C15	0.059 (6)	0.032 (5)	0.040 (5)	0.010 (4)	0.013 (4)	0.003 (3)

Geometric parameters (Å, º)

Se1—C2	1.861 (7)	C23—H23	0.9500
Se1—C5	1.870 (7)	C24—C25	1.361 (10)
S21—C25	1.706 (8)	C24—H24	0.9500
S21—C22	1.732 (7)	C25—H25	0.9500
S11—C12	1.707 (8)	C2—C12	1.471 (9)
S11—C15	1.714 (8)	C12—C13	1.386 (10)
N4—C5	1.295 (10)	C13—C14	1.420 (12)
N4—N3	1.357 (8)	C13—H13	0.9500
N3—C2	1.309 (8)	C14—C15	1.351 (10)
C5—C22	1.454 (9)	C14—H14	0.9500
C22—C23	1.383 (11)	C15—H15	0.9500
C23—C24	1.408 (12)
C2—Se1—C5	81.7 (3)	C24—C25—H25	123.6
C25—S21—C22	91.1 (4)	S21—C25—H25	123.6
C12—S11—C15	91.3 (4)	N3—C2—C12	120.2 (6)
C5—N4—N3	114.9 (7)	N3—C2—Se1	114.5 (5)
C2—N3—N4	114.4 (6)	C12—C2—Se1	125.3 (5)
N4—C5—C22	122.1 (6)	C13—C12—C2	128.3 (7)
N4—C5—Se1	114.5 (6)	C13—C12—S11	112.1 (6)
C22—C5—Se1	123.3 (5)	C2—C12—S11	119.4 (5)
C23—C22—C5	129.2 (7)	C12—C13—C14	111.2 (7)
C23—C22—S21	111.3 (6)	C12—C13—H13	124.4
C5—C22—S21	119.5 (5)	C14—C13—H13	124.4
C22—C23—C24	112.1 (8)	C15—C14—C13	112.8 (7)
C22—C23—H23	123.9	C15—C14—H14	123.6
C24—C23—H23	123.9	C13—C14—H14	123.6
C25—C24—C23	112.7 (7)	C14—C15—S11	112.5 (6)
C25—C24—H24	123.6	C14—C15—H15	123.8
C23—C24—H24	123.6	S11—C15—H15	123.8
C24—C25—S21	112.7 (6)
C5—N4—N3—C2	0.6 (9)	N4—N3—C2—C12	−178.4 (6)
N3—N4—C5—C22	−178.9 (6)	N4—N3—C2—Se1	0.2 (8)
N3—N4—C5—Se1	−1.1 (8)	C5—Se1—C2—N3	−0.6 (5)
C2—Se1—C5—N4	0.9 (6)	C5—Se1—C2—C12	177.9 (6)
C2—Se1—C5—C22	178.7 (6)	N3—C2—C12—C13	179.0 (7)
N4—C5—C22—C23	−174.2 (8)	Se1—C2—C12—C13	0.5 (11)
Se1—C5—C22—C23	8.2 (11)	N3—C2—C12—S11	−5.3 (9)
N4—C5—C22—S21	5.0 (9)	Se1—C2—C12—S11	176.3 (4)
Se1—C5—C22—S21	−172.7 (4)	C15—S11—C12—C13	−2.1 (6)
C25—S21—C22—C23	−0.2 (6)	C15—S11—C12—C2	−178.5 (6)
C25—S21—C22—C5	−179.5 (6)	C2—C12—C13—C14	177.8 (7)
C5—C22—C23—C24	178.4 (7)	S11—C12—C13—C14	1.7 (9)
S21—C22—C23—C24	−0.8 (9)	C12—C13—C14—C15	−0.3 (10)
C22—C23—C24—C25	1.7 (11)	C13—C14—C15—S11	−1.3 (9)
C23—C24—C25—S21	−1.8 (9)	C12—S11—C15—C14	1.9 (6)
C22—S21—C25—C24	1.1 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C23—H23···N4^i	0.95	2.59	3.539 (12)	177

Symmetry code: (i) x−1/2, −y+1, z.

(III) 2-(4-chlorophenyl)-5-phenyl-1,3,4-selenadiazole

Crystal data

C14H9ClN2Se	F(000) = 632
Mr = 319.64	Dx = 1.743 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4092 reflections
a = 13.382 (5) Å	θ = 2.5–28.3°
b = 5.5247 (18) Å	µ = 3.28 mm^−1
c = 16.524 (5) Å	T = 93 K
β = 94.528 (8)°	Platelet, colourless
V = 1217.9 (7) Å^3	0.12 × 0.07 × 0.01 mm
Z = 4

Data collection

Rigaku Mercury CCD area-detector diffractometer	2513 independent reflections
Radiation source: rotating anode	2050 reflections with I > 2σ(I)
Confocal monochromator	Rint = 0.058
Detector resolution: 14.7059 pixels mm^-1	θmax = 28.4°, θmin = 2.5°
ω and ϕ scans	h = −16→15
Absorption correction: multi-scan (CrystalClear; Rigaku, 2010)	k = −7→4
Tmin = 0.500, Tmax = 1.000	l = −15→21
7679 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.079	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.226	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.1375P)^2 + 2.8891P] where P = (Fo^2 + 2Fc^2)/3
2513 reflections	(Δ/σ)max = 0.001
163 parameters	Δρmax = 4.87 e Å^−3
0 restraints	Δρmin = −1.07 e Å^−3

Special details

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. A q-peak comprising 4.87 e^- Å^-3 was located 1.37 Å from Se1.

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

	x	y	z	Uiso*/Ueq
Se1	0.58869 (4)	0.11522 (10)	0.70232 (4)	0.0261 (3)
Cl1	0.12692 (11)	0.0260 (3)	0.45025 (10)	0.0373 (5)
N3	0.5849 (4)	−0.2964 (10)	0.6164 (3)	0.0257 (11)
N4	0.6764 (4)	−0.2978 (10)	0.6608 (3)	0.0309 (12)
C2	0.5288 (5)	−0.1089 (10)	0.6283 (4)	0.0260 (14)
C5	0.6941 (5)	−0.1088 (10)	0.7076 (4)	0.0242 (13)
C11	0.4298 (4)	−0.0772 (11)	0.5848 (3)	0.0214 (12)
C12	0.3720 (5)	0.1270 (11)	0.5985 (4)	0.0284 (15)
H12	0.3969	0.2451	0.6368	0.034*
C13	0.2787 (5)	0.1596 (12)	0.5569 (4)	0.0278 (14)
H13	0.2396	0.2994	0.5657	0.033*
C14	0.2441 (4)	−0.0182 (12)	0.5021 (4)	0.0307 (14)
C15	0.2990 (4)	−0.2191 (12)	0.4869 (4)	0.0272 (13)
H15	0.2745	−0.3350	0.4477	0.033*
C16	0.3917 (5)	−0.2500 (11)	0.5300 (4)	0.0288 (13)
H16	0.4296	−0.3921	0.5216	0.035*
C21	0.7874 (4)	−0.0788 (11)	0.7598 (4)	0.0242 (13)
C22	0.8030 (5)	0.1245 (10)	0.8100 (4)	0.0268 (14)
H22	0.7539	0.2487	0.8096	0.032*
C23	0.8912 (5)	0.1431 (12)	0.8605 (4)	0.0306 (15)
H23	0.9009	0.2825	0.8939	0.037*
C24	0.9644 (4)	−0.0303 (11)	0.8642 (4)	0.0253 (12)
H24	1.0231	−0.0167	0.9001	0.030*
C25	0.9475 (5)	−0.2357 (13)	0.8104 (4)	0.0314 (14)
H25	0.9971	−0.3583	0.8093	0.038*
C26	0.8609 (5)	−0.2551 (11)	0.7612 (4)	0.0265 (13)
H26	0.8509	−0.3928	0.7271	0.032*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Se1	0.0309 (5)	0.0185 (5)	0.0290 (5)	0.0025 (2)	0.0037 (3)	−0.0032 (2)
Cl1	0.0318 (8)	0.0449 (11)	0.0345 (10)	−0.0007 (7)	−0.0024 (6)	0.0027 (7)
N3	0.028 (2)	0.021 (3)	0.028 (3)	0.006 (2)	0.0023 (19)	−0.005 (2)
N4	0.028 (3)	0.027 (3)	0.038 (3)	0.001 (2)	0.003 (2)	−0.003 (2)
C2	0.035 (3)	0.015 (3)	0.029 (4)	−0.003 (2)	0.008 (3)	0.002 (2)
C5	0.030 (3)	0.017 (3)	0.026 (3)	−0.003 (2)	0.008 (2)	0.000 (2)
C11	0.026 (3)	0.019 (3)	0.020 (3)	−0.003 (2)	0.009 (2)	0.003 (2)
C12	0.035 (3)	0.022 (3)	0.029 (4)	0.002 (2)	0.003 (3)	0.001 (2)
C13	0.035 (3)	0.021 (3)	0.028 (3)	0.007 (3)	0.008 (3)	0.003 (3)
C14	0.027 (3)	0.032 (4)	0.034 (4)	0.000 (3)	0.008 (2)	0.007 (3)
C15	0.028 (3)	0.025 (3)	0.028 (3)	−0.005 (2)	0.004 (2)	−0.004 (3)
C16	0.031 (3)	0.020 (3)	0.036 (3)	0.002 (2)	0.008 (2)	−0.006 (3)
C21	0.025 (3)	0.019 (3)	0.029 (3)	−0.002 (2)	0.009 (2)	0.004 (2)
C22	0.032 (3)	0.020 (3)	0.029 (4)	0.000 (2)	0.010 (3)	−0.003 (2)
C23	0.036 (3)	0.025 (3)	0.031 (4)	−0.009 (3)	0.005 (3)	−0.008 (3)
C24	0.025 (3)	0.025 (3)	0.027 (3)	−0.001 (2)	0.005 (2)	0.005 (3)
C25	0.033 (3)	0.030 (4)	0.032 (4)	0.005 (3)	0.004 (3)	0.004 (3)
C26	0.033 (3)	0.020 (3)	0.027 (3)	−0.001 (2)	0.007 (2)	0.002 (2)

Geometric parameters (Å, º)

Se1—C5	1.874 (6)	C15—C16	1.391 (9)
Se1—C2	1.875 (6)	C15—H15	0.9500
Cl1—C14	1.744 (7)	C16—H16	0.9500
N3—C2	1.304 (8)	C21—C26	1.383 (9)
N3—N4	1.378 (7)	C21—C22	1.402 (8)
N4—C5	1.309 (8)	C22—C23	1.394 (10)
C2—C11	1.467 (9)	C22—H22	0.9500
C5—C21	1.470 (9)	C23—C24	1.368 (9)
C11—C16	1.386 (8)	C23—H23	0.9500
C11—C12	1.396 (9)	C24—C25	1.448 (9)
C12—C13	1.389 (9)	C24—H24	0.9500
C12—H12	0.9500	C25—C26	1.366 (9)
C13—C14	1.390 (10)	C25—H25	0.9500
C13—H13	0.9500	C26—H26	0.9500
C14—C15	1.366 (9)
C5—Se1—C2	82.9 (3)	C16—C15—H15	120.8
C2—N3—N4	115.0 (5)	C11—C16—C15	121.1 (6)
C5—N4—N3	115.0 (5)	C11—C16—H16	119.4
N3—C2—C11	122.0 (6)	C15—C16—H16	119.4
N3—C2—Se1	113.7 (5)	C26—C21—C22	118.8 (6)
C11—C2—Se1	124.3 (4)	C26—C21—C5	120.0 (6)
N4—C5—C21	122.8 (5)	C22—C21—C5	121.2 (5)
N4—C5—Se1	113.5 (5)	C23—C22—C21	119.5 (6)
C21—C5—Se1	123.7 (4)	C23—C22—H22	120.2
C16—C11—C12	118.9 (6)	C21—C22—H22	120.2
C16—C11—C2	120.6 (5)	C24—C23—C22	122.9 (6)
C12—C11—C2	120.5 (6)	C24—C23—H23	118.5
C13—C12—C11	120.8 (6)	C22—C23—H23	118.5
C13—C12—H12	119.6	C23—C24—C25	116.4 (6)
C11—C12—H12	119.6	C23—C24—H24	121.8
C12—C13—C14	118.1 (6)	C25—C24—H24	121.8
C12—C13—H13	121.0	C26—C25—C24	120.7 (6)
C14—C13—H13	121.0	C26—C25—H25	119.6
C15—C14—C13	122.6 (6)	C24—C25—H25	119.6
C15—C14—Cl1	119.9 (5)	C25—C26—C21	121.5 (6)
C13—C14—Cl1	117.5 (5)	C25—C26—H26	119.2
C14—C15—C16	118.4 (6)	C21—C26—H26	119.2
C14—C15—H15	120.8
C2—N3—N4—C5	−1.0 (8)	C13—C14—C15—C16	2.2 (10)
N4—N3—C2—C11	179.0 (5)	Cl1—C14—C15—C16	−179.3 (5)
N4—N3—C2—Se1	1.0 (7)	C12—C11—C16—C15	2.1 (9)
C5—Se1—C2—N3	−0.6 (5)	C2—C11—C16—C15	−178.4 (5)
C5—Se1—C2—C11	−178.5 (5)	C14—C15—C16—C11	−2.6 (9)
N3—N4—C5—C21	179.7 (5)	N4—C5—C21—C26	−0.3 (9)
N3—N4—C5—Se1	0.5 (7)	Se1—C5—C21—C26	178.9 (5)
C2—Se1—C5—N4	0.1 (5)	N4—C5—C21—C22	−179.1 (6)
C2—Se1—C5—C21	−179.2 (5)	Se1—C5—C21—C22	0.1 (8)
N3—C2—C11—C16	1.1 (9)	C26—C21—C22—C23	−0.7 (9)
Se1—C2—C11—C16	178.9 (5)	C5—C21—C22—C23	178.1 (6)
N3—C2—C11—C12	−179.4 (6)	C21—C22—C23—C24	−0.4 (10)
Se1—C2—C11—C12	−1.6 (8)	C22—C23—C24—C25	1.8 (10)
C16—C11—C12—C13	−1.2 (9)	C23—C24—C25—C26	−2.1 (9)
C2—C11—C12—C13	179.3 (6)	C24—C25—C26—C21	1.1 (9)
C11—C12—C13—C14	0.8 (10)	C22—C21—C26—C25	0.4 (9)
C12—C13—C14—C15	−1.3 (10)	C5—C21—C26—C25	−178.4 (6)
C12—C13—C14—Cl1	−179.8 (5)

(IV) 2-(furan-2-yl)-5-(p-tolyl)-1,3,4-selenadiazole

Crystal data

C13H10N2OSe	F(000) = 1152
Mr = 289.19	Dx = 1.624 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7011 reflections
a = 8.5036 (15) Å	θ = 2.4–28.1°
b = 25.210 (5) Å	µ = 3.16 mm^−1
c = 11.116 (2) Å	T = 93 K
β = 96.814 (5)°	Platelet, colourless
V = 2366.2 (8) Å^3	0.30 × 0.20 × 0.04 mm
Z = 8

Data collection

Rigaku Mercury CCD area-detector diffractometer	4865 independent reflections
Radiation source: rotating anode	3778 reflections with I > 2σ(I)
Confocal monochromator	Rint = 0.055
Detector resolution: 14.7059 pixels mm^-1	θmax = 28.4°, θmin = 2.4°
ω and ϕ scans	h = −8→10
Absorption correction: multi-scan (CrystalClear; Rigaku, 2010)	k = −30→30
Tmin = 0.558, Tmax = 1.000	l = −8→13
15690 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.147	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0627P)^2 + 3.0274P] where P = (Fo^2 + 2Fc^2)/3
4865 reflections	(Δ/σ)max < 0.001
309 parameters	Δρmax = 1.35 e Å^−3
0 restraints	Δρmin = −1.03 e Å^−3

Special details

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	0.95776 (5)	0.609805 (19)	0.54769 (5)	0.03479 (17)
Se31	0.41752 (5)	0.571510 (18)	0.69908 (4)	0.03316 (17)
O11	0.9742 (4)	0.71563 (15)	0.3949 (4)	0.0497 (10)
O41	0.4615 (5)	0.67205 (18)	0.5440 (4)	0.0678 (13)
N4	0.6889 (4)	0.56170 (15)	0.4536 (4)	0.0306 (9)
N3	0.6937 (4)	0.60813 (15)	0.3890 (4)	0.0324 (9)
N34	0.2462 (5)	0.60326 (16)	0.8742 (4)	0.0372 (10)
N33	0.2606 (5)	0.64772 (16)	0.8048 (4)	0.0384 (10)
C5	0.8087 (5)	0.55386 (18)	0.5365 (4)	0.0286 (10)
C2	0.8173 (5)	0.63757 (19)	0.4200 (4)	0.0304 (10)
C21	0.8273 (5)	0.50612 (17)	0.6113 (4)	0.0268 (9)
C26	0.6987 (5)	0.47135 (18)	0.6129 (4)	0.0310 (10)
H26	0.6004	0.4794	0.5666	0.037*
C25	0.7142 (5)	0.42556 (18)	0.6815 (4)	0.0308 (10)
H25	0.6254	0.4027	0.6817	0.037*
C24	0.8558 (5)	0.4119 (2)	0.7503 (4)	0.0323 (10)
C23	0.9839 (5)	0.4469 (2)	0.7475 (4)	0.0331 (10)
H23	1.0825	0.4388	0.7934	0.040*
C22	0.9694 (5)	0.49260 (19)	0.6792 (4)	0.0311 (10)
H22	1.0584	0.5153	0.6786	0.037*
C27	0.8695 (6)	0.36290 (19)	0.8269 (5)	0.0377 (11)
H27A	0.8035	0.3348	0.7863	0.057*
H27B	0.8338	0.3706	0.9057	0.057*
H27C	0.9802	0.3512	0.8387	0.057*
C12	0.8435 (6)	0.68595 (18)	0.3572 (5)	0.0356 (11)
C13	0.7610 (6)	0.7077 (2)	0.2594 (5)	0.0389 (12)
H13	0.6661	0.6946	0.2158	0.047*
C14	0.8455 (8)	0.7547 (2)	0.2340 (6)	0.0548 (15)
H14	0.8167	0.7792	0.1701	0.066*
C15	0.9705 (8)	0.7578 (2)	0.3158 (6)	0.0567 (16)
H15	1.0474	0.7853	0.3198	0.068*
C35	0.3168 (5)	0.56102 (18)	0.8394 (4)	0.0292 (10)
C32	0.3422 (5)	0.64067 (18)	0.7134 (4)	0.0324 (10)
C51	0.3128 (5)	0.50983 (18)	0.9003 (4)	0.0297 (10)
C56	0.2204 (5)	0.50328 (19)	0.9959 (4)	0.0343 (11)
H56	0.1633	0.5325	1.0228	0.041*
C55	0.2123 (5)	0.4544 (2)	1.0509 (4)	0.0369 (11)
H55	0.1489	0.4505	1.1152	0.044*
C54	0.2948 (5)	0.4107 (2)	1.0144 (4)	0.0330 (11)
C53	0.3882 (5)	0.41835 (19)	0.9207 (4)	0.0343 (11)
H53	0.4478	0.3894	0.8956	0.041*
C52	0.3967 (5)	0.46653 (18)	0.8636 (4)	0.0309 (10)
H52	0.4599	0.4702	0.7991	0.037*
C57	0.2820 (6)	0.3572 (2)	1.0735 (5)	0.0440 (13)
H57A	0.3843	0.3390	1.0783	0.066*
H57B	0.2011	0.3359	1.0253	0.066*
H57C	0.2522	0.3620	1.1553	0.066*
C42	0.3657 (5)	0.68200 (19)	0.6294 (5)	0.0361 (11)
C43	0.3075 (6)	0.73151 (19)	0.6209 (5)	0.0462 (14)
H43	0.2410	0.7479	0.6729	0.055*
C44	0.3665 (7)	0.7546 (3)	0.5173 (6)	0.0624 (18)
H44	0.3451	0.7891	0.4850	0.075*
C45	0.4572 (8)	0.7176 (3)	0.4759 (6)	0.071 (2)
H45	0.5127	0.7220	0.4073	0.085*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Se1	0.0310 (3)	0.0369 (3)	0.0357 (3)	−0.00673 (18)	0.0011 (2)	−0.0054 (2)
Se31	0.0366 (3)	0.0307 (3)	0.0337 (3)	0.00295 (18)	0.0105 (2)	−0.0041 (2)
O11	0.046 (2)	0.046 (2)	0.058 (3)	−0.0118 (17)	0.0119 (18)	−0.0026 (19)
O41	0.075 (3)	0.058 (3)	0.080 (3)	0.000 (2)	0.043 (3)	0.005 (2)
N4	0.028 (2)	0.034 (2)	0.030 (2)	−0.0026 (15)	0.0064 (16)	−0.0003 (18)
N3	0.031 (2)	0.034 (2)	0.032 (2)	−0.0020 (16)	0.0049 (16)	−0.0014 (18)
N34	0.042 (2)	0.036 (2)	0.033 (2)	0.0092 (17)	0.0061 (18)	−0.0014 (19)
N33	0.046 (2)	0.036 (2)	0.033 (2)	0.0094 (18)	0.0073 (19)	−0.0045 (19)
C5	0.023 (2)	0.038 (3)	0.025 (2)	0.0004 (18)	0.0060 (17)	−0.006 (2)
C2	0.026 (2)	0.035 (2)	0.031 (3)	−0.0021 (18)	0.0073 (18)	−0.006 (2)
C21	0.026 (2)	0.033 (2)	0.021 (2)	−0.0016 (17)	0.0056 (17)	−0.007 (2)
C26	0.026 (2)	0.037 (3)	0.030 (3)	−0.0029 (18)	0.0059 (18)	−0.005 (2)
C25	0.025 (2)	0.036 (3)	0.033 (3)	−0.0040 (18)	0.0084 (19)	−0.005 (2)
C24	0.032 (3)	0.040 (3)	0.027 (3)	0.004 (2)	0.0080 (19)	−0.005 (2)
C23	0.028 (2)	0.043 (3)	0.029 (3)	0.002 (2)	0.0006 (18)	−0.005 (2)
C22	0.028 (2)	0.039 (3)	0.026 (2)	−0.0021 (19)	0.0016 (18)	−0.006 (2)
C27	0.042 (3)	0.036 (3)	0.037 (3)	0.001 (2)	0.009 (2)	0.000 (2)
C12	0.040 (3)	0.028 (2)	0.041 (3)	−0.0066 (19)	0.016 (2)	−0.008 (2)
C13	0.036 (3)	0.041 (3)	0.040 (3)	0.001 (2)	0.004 (2)	−0.003 (2)
C14	0.073 (4)	0.040 (3)	0.055 (4)	0.010 (3)	0.026 (3)	0.009 (3)
C15	0.077 (4)	0.032 (3)	0.068 (4)	−0.009 (3)	0.036 (4)	0.001 (3)
C35	0.029 (2)	0.031 (2)	0.026 (2)	0.0024 (18)	−0.0024 (18)	−0.008 (2)
C32	0.030 (2)	0.032 (3)	0.033 (3)	0.0024 (18)	−0.0024 (19)	−0.003 (2)
C51	0.028 (2)	0.034 (2)	0.027 (2)	0.0026 (18)	−0.0025 (18)	−0.005 (2)
C56	0.036 (3)	0.039 (3)	0.029 (3)	−0.001 (2)	0.006 (2)	−0.007 (2)
C55	0.033 (3)	0.048 (3)	0.029 (3)	−0.003 (2)	0.0031 (19)	−0.001 (2)
C54	0.031 (3)	0.039 (3)	0.028 (3)	−0.003 (2)	−0.0013 (19)	0.001 (2)
C53	0.030 (3)	0.036 (3)	0.036 (3)	0.0029 (19)	0.002 (2)	−0.006 (2)
C52	0.027 (2)	0.037 (3)	0.030 (3)	0.0001 (18)	0.0064 (18)	−0.002 (2)
C57	0.047 (3)	0.046 (3)	0.038 (3)	−0.007 (2)	0.002 (2)	0.005 (3)
C42	0.033 (3)	0.036 (3)	0.040 (3)	−0.0008 (19)	0.004 (2)	−0.005 (2)
C43	0.063 (4)	0.027 (3)	0.054 (4)	0.009 (2)	0.032 (3)	0.012 (3)
C44	0.056 (4)	0.053 (4)	0.079 (5)	0.000 (3)	0.009 (3)	0.033 (4)
C45	0.073 (5)	0.092 (6)	0.053 (4)	−0.018 (4)	0.031 (3)	−0.001 (4)

Geometric parameters (Å, º)

Se1—C2	1.879 (5)	C27—H27C	0.9800
Se1—C5	1.890 (4)	C12—C13	1.339 (7)
Se31—C32	1.871 (5)	C13—C14	1.432 (7)
Se31—C35	1.885 (5)	C13—H13	0.9500
O11—C12	1.363 (6)	C14—C15	1.317 (9)
O11—C15	1.378 (7)	C14—H14	0.9500
O41—C42	1.346 (6)	C15—H15	0.9500
O41—C45	1.372 (8)	C35—C51	1.460 (6)
N4—C5	1.305 (6)	C32—C42	1.429 (7)
N4—N3	1.377 (5)	C51—C52	1.392 (6)
N3—C2	1.299 (6)	C51—C56	1.405 (6)
N34—C35	1.303 (6)	C56—C55	1.381 (7)
N34—N33	1.374 (6)	C56—H56	0.9500
N33—C32	1.309 (6)	C55—C54	1.392 (7)
C5—C21	1.461 (6)	C55—H55	0.9500
C2—C12	1.436 (7)	C54—C53	1.396 (7)
C21—C22	1.389 (6)	C54—C57	1.511 (7)
C21—C26	1.403 (6)	C53—C52	1.377 (6)
C26—C25	1.381 (6)	C53—H53	0.9500
C26—H26	0.9500	C52—H52	0.9500
C25—C24	1.391 (6)	C57—H57A	0.9800
C25—H25	0.9500	C57—H57B	0.9800
C24—C23	1.405 (7)	C57—H57C	0.9800
C24—C27	1.497 (7)	C42—C43	1.342 (6)
C23—C22	1.378 (7)	C43—C44	1.433 (8)
C23—H23	0.9500	C43—H43	0.9500
C22—H22	0.9500	C44—C45	1.328 (9)
C27—H27A	0.9800	C44—H44	0.9500
C27—H27B	0.9800	C45—H45	0.9500
C2—Se1—C5	82.36 (19)	C13—C14—H14	126.4
C32—Se31—C35	82.3 (2)	C14—C15—O11	110.5 (5)
C12—O11—C15	105.8 (4)	C14—C15—H15	124.8
C42—O41—C45	104.7 (5)	O11—C15—H15	124.8
C5—N4—N3	115.4 (4)	N34—C35—C51	123.2 (4)
C2—N3—N4	114.8 (4)	N34—C35—Se31	113.7 (4)
C35—N34—N33	115.2 (4)	C51—C35—Se31	123.1 (3)
C32—N33—N34	114.5 (4)	N33—C32—C42	122.5 (4)
N4—C5—C21	123.3 (4)	N33—C32—Se31	114.3 (4)
N4—C5—Se1	113.2 (3)	C42—C32—Se31	123.2 (4)
C21—C5—Se1	123.4 (3)	C52—C51—C56	118.8 (4)
N3—C2—C12	121.6 (4)	C52—C51—C35	121.1 (4)
N3—C2—Se1	114.2 (4)	C56—C51—C35	120.1 (4)
C12—C2—Se1	124.2 (3)	C55—C56—C51	120.1 (4)
C22—C21—C26	118.0 (4)	C55—C56—H56	119.9
C22—C21—C5	122.7 (4)	C51—C56—H56	119.9
C26—C21—C5	119.3 (4)	C56—C55—C54	121.5 (5)
C25—C26—C21	120.4 (4)	C56—C55—H55	119.2
C25—C26—H26	119.8	C54—C55—H55	119.2
C21—C26—H26	119.8	C55—C54—C53	117.4 (5)
C26—C25—C24	122.0 (4)	C55—C54—C57	121.0 (4)
C26—C25—H25	119.0	C53—C54—C57	121.6 (5)
C24—C25—H25	119.0	C52—C53—C54	122.1 (4)
C25—C24—C23	117.1 (4)	C52—C53—H53	118.9
C25—C24—C27	121.4 (4)	C54—C53—H53	118.9
C23—C24—C27	121.5 (4)	C53—C52—C51	120.0 (4)
C22—C23—C24	121.2 (4)	C53—C52—H52	120.0
C22—C23—H23	119.4	C51—C52—H52	120.0
C24—C23—H23	119.4	C54—C57—H57A	109.5
C23—C22—C21	121.3 (4)	C54—C57—H57B	109.5
C23—C22—H22	119.3	H57A—C57—H57B	109.5
C21—C22—H22	119.3	C54—C57—H57C	109.5
C24—C27—H27A	109.5	H57A—C57—H57C	109.5
C24—C27—H27B	109.5	H57B—C57—H57C	109.5
H27A—C27—H27B	109.5	C43—C42—O41	111.9 (5)
C24—C27—H27C	109.5	C43—C42—C32	130.1 (5)
H27A—C27—H27C	109.5	O41—C42—C32	117.9 (4)
H27B—C27—H27C	109.5	C42—C43—C44	105.8 (5)
C13—C12—O11	110.7 (4)	C42—C43—H43	127.1
C13—C12—C2	130.2 (5)	C44—C43—H43	127.1
O11—C12—C2	119.0 (5)	C45—C44—C43	105.4 (5)
C12—C13—C14	105.8 (5)	C45—C44—H44	127.3
C12—C13—H13	127.1	C43—C44—H44	127.3
C14—C13—H13	127.1	C44—C45—O41	112.1 (6)
C15—C14—C13	107.2 (5)	C44—C45—H45	124.0
C15—C14—H14	126.4	O41—C45—H45	124.0
C5—N4—N3—C2	0.0 (6)	C12—O11—C15—C14	0.0 (6)
C35—N34—N33—C32	0.6 (6)	N33—N34—C35—C51	−179.0 (4)
N3—N4—C5—C21	−177.8 (4)	N33—N34—C35—Se31	−1.4 (5)
N3—N4—C5—Se1	1.0 (5)	C32—Se31—C35—N34	1.3 (3)
C2—Se1—C5—N4	−1.2 (3)	C32—Se31—C35—C51	178.9 (4)
C2—Se1—C5—C21	177.7 (4)	N34—N33—C32—C42	178.2 (4)
N4—N3—C2—C12	176.9 (4)	N34—N33—C32—Se31	0.5 (5)
N4—N3—C2—Se1	−0.9 (5)	C35—Se31—C32—N33	−1.0 (4)
C5—Se1—C2—N3	1.2 (3)	C35—Se31—C32—C42	−178.6 (4)
C5—Se1—C2—C12	−176.6 (4)	N34—C35—C51—C52	−176.7 (4)
N4—C5—C21—C22	165.2 (4)	Se31—C35—C51—C52	6.0 (6)
Se1—C5—C21—C22	−13.5 (6)	N34—C35—C51—C56	4.7 (7)
N4—C5—C21—C26	−12.9 (6)	Se31—C35—C51—C56	−172.6 (3)
Se1—C5—C21—C26	168.4 (3)	C52—C51—C56—C55	−0.8 (6)
C22—C21—C26—C25	0.8 (6)	C35—C51—C56—C55	177.8 (4)
C5—C21—C26—C25	179.0 (4)	C51—C56—C55—C54	0.3 (7)
C21—C26—C25—C24	−0.4 (7)	C56—C55—C54—C53	0.9 (7)
C26—C25—C24—C23	0.0 (7)	C56—C55—C54—C57	−178.6 (4)
C26—C25—C24—C27	178.3 (4)	C55—C54—C53—C52	−1.6 (7)
C25—C24—C23—C22	0.0 (7)	C57—C54—C53—C52	177.9 (4)
C27—C24—C23—C22	−178.3 (4)	C54—C53—C52—C51	1.2 (7)
C24—C23—C22—C21	0.4 (7)	C56—C51—C52—C53	0.0 (6)
C26—C21—C22—C23	−0.8 (7)	C35—C51—C52—C53	−178.5 (4)
C5—C21—C22—C23	−179.0 (4)	C45—O41—C42—C43	−2.3 (7)
C15—O11—C12—C13	0.2 (6)	C45—O41—C42—C32	178.2 (5)
C15—O11—C12—C2	177.8 (4)	N33—C32—C42—C43	−4.3 (8)
N3—C2—C12—C13	−3.9 (8)	Se31—C32—C42—C43	173.1 (5)
Se1—C2—C12—C13	173.7 (4)	N33—C32—C42—O41	175.0 (5)
N3—C2—C12—O11	179.1 (4)	Se31—C32—C42—O41	−7.6 (6)
Se1—C2—C12—O11	−3.3 (6)	O41—C42—C43—C44	2.6 (7)
O11—C12—C13—C14	−0.4 (6)	C32—C42—C43—C44	−178.1 (5)
C2—C12—C13—C14	−177.6 (5)	C42—C43—C44—C45	−1.7 (7)
C12—C13—C14—C15	0.4 (6)	C43—C44—C45—O41	0.3 (8)
C13—C14—C15—O11	−0.3 (6)	C42—O41—C45—C44	1.2 (8)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···N33^i	0.95	2.50	3.441 (7)	172
C44—H44···N33^ii	0.95	2.59	3.457 (7)	151

Symmetry codes: (i) x+1, −y+3/2, z−1/2; (ii) x, −y+3/2, z−1/2.