Structural characterization of selenium and selenium-diiodine analogues of the antithyroid drug 6-n-propyl-2-thiouracil and its alkyl derivatives

Antoniadis, C.D.; Blake, A.J.; Hadjikakou, S.K.; Hadjiliadis, N.; Hubberstey, P.; Schröder, M.; Wilson, C.

doi:10.1107/S0108768106011426

research papers

STRUCTURAL SCIENCE
CRYSTAL ENGINEERING
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ISSN: 2052-5206

Volume 62| Part 4| August 2006| Pages 580-591

doi:10.1107/S0108768106011426

Structural characterization of selenium and selenium-diiodine analogues of the antithyroid drug 6-n-propyl-2-thiouracil and its alkyl derivatives

Constantinos D. Antoniadis,^a Alexander J. Blake,^b ^* Sotiris K. Hadjikakou,^a Nick Hadjiliadis,^a Peter Hubberstey,^b Martin Schröder ^b and Claire Wilson ^b

^aSection of Inorganic and Analytical Chemistry, Department of Chemistry, University of Ioannina, 45110 Ioannina, Greece, and ^bSchool of Chemistry, The University of Nottingham, University Park, Nottingham NG7 2RD, England
^*Correspondence e-mail: a.j.blake@nottingham.ac.uk

(Received 8 March 2006; accepted 29 March 2006)

The structures of four selenium analogues of the antithyroid drug 6-n-propyl-2-thiouracil [systematic name: 2,3-dihydro-6-n-propyl-2-thioxopyrimidin-4(1H)-one], namely 6-methyl-2-selenouracil, C₅H₆N₂OSe (1), 6-ethyl-2-selenouracil, C₆H₈N₂OSe (2), 6-n-propyl-2-selenouracil, C₇H₁₀N₂OSe (3), and 6-isopropyl-2-selenouracil, C₇H₁₀N₂OSe (4), are described, along with that of the dichloromethane monosolvate of 6-isopropyl-2-selenouracil, C₇H₁₀N₂OSe·CH₂Cl₂ (4·CH₂Cl₂). The extended structure of (1) is a two-dimensional sheet of topology 6³ with a brick-wall architecture. The extended structures of (2) and (4) are analogous, being based on a chain of eight-membered R₈⁶(32) hydrogen-bonded rings. In (3) and (4·CH₂Cl₂), R₂²(8) hydrogen bonding links molecules into chains. 6-n-Propyl-2-selenouracil·I₂, C₇H₁₀N₂OSe·I₂ (7), is a charge-transfer complex with a `spoke' structure, the extended structure of which is based on a linear chain formed principally by intermolecular N—H⋯O hydrogen bonds. Re-crystallization of 6-ethyl-2-selenouracil or (7) from acetone gave crystals of the diselenides [N-(6′-ethyl-4′-pyrimidone)(6-ethyl-2-selenouracil)₂(Se—Se)]·2H₂O (9·2H₂O) or [N-(6′-n-propyl-4′-pyrimidone)(6-n-propyl-2-selenouracil)₂(Se—Se)] (10), respectively: these have similar extended chain structures formed via N—H⋯O and C—H⋯O hydrogen bonds, stacked to give two-dimensional sheets. Re-crystallization of (7) from methanol/acetonitrile led via deselenation to the formation of crystals of 6-n-propyl-2-uracil (11), in which six symmetry-related molecules combine to form a six-membered R₆⁶(24) hydrogen-bonded ring, with each pair of molecules linked by an R₂²(8) motif.

Keywords: selenouracil; hydrogen bonding; charge-transfer complex; antithyroid drug.

1. Introduction

Prior to 1960, no uncharged covalent compounds between selenium and iodine had been discovered (Dasent, 1965 ). It was during the decade 1960–1969 that the structures of the first selenoether–iodine complexes were first reported (Chao & McCullough, 1961 ; Hope & McCullough, 1962 ; Maddox & McCullough, 1966 ; Bjorvatten, 1963 ; Dahl & Hassel, 1965 ; Holmesland & Römming, 1966 ; Bent, 1968 ). Currently, organic selones and/or selenoamides are recognized as potential donors towards diiodine and some iodine-containing compounds, generating charge-transfer complexes that are generally more stable than those of the corresponding sulfur ligands (e.g. du Mont et al., 2001 ). The reactions between selones or selenoamides with diiodine I₂ or interhalogens I—X (X = Br or Cl) lead to the formation of iodine charge-transfer complexes (Aragoni et al., 1999 , and references therein), which adopt a number of structures including:

(i) `spoke structures' or `extended spoke structures' bearing a linear arrangement of Se—I—X (X = I, Br or Cl) or Se—I—I⋯I—I groups;
(ii) two-coordinate iodine(I) cationic or iodonium salts with selone ligands ([LSe—X—SeL]);
(iii) donor oxidation products including dicationic diselenides [LSe—SeL]²⁺·2I₃⁻ or neutral diselenides; and
(iv) T-shaped compounds containing the linear group I—Se—X (X = I, Br or Cl; Aragoni et al., 2001 , and references therein).

The mono-cationic diselenide geometry is the only interaction not yet observed in products of reactions between iodine and selones. As part of a study of charge-transfer complexes with iodine and polyiodides (Blake et al., 1995

; Blake, Devillanova, Garau et al., 1998

; Blake, Devillanova, Gould et al., 1998

; Blake, Li et al., 1998

), we report herein the structures of 6-n-propyl-2-selenouracil·I₂, 6-n-propyl-2-selenouracil itself, some selenium analogues of 6-alkyl-2-thiouracils, two diselenides and the deselenation product 6-n-propyl-2-uracil.

2. Experimental

2.1. Synthesis and crystal growth

The preparative details for all nine compounds [see Scheme (I)] have been reported previously (Antoniadis et al., 2006 ). Compounds (1), (2), (3) and (4) were re-crystallized from water to give colourless crystals, while re-crystallization of (4)

from dichloromethane gave crystals of (4·CH₂Cl₂). Crystals of (7) were grown from chloroform solutions, while re-crystallization of (6) and (7) from acetone gave the oxidation products (9·2H₂O) and (10), respectively. Re-crystallization of (7) from methanol/acetonitrile led via deselenation to crystals of 6-n-propyl-2-uracil (11).

2.2. Data collection, structure solution and refinement

Details of cell data, data collection and structure solution and refinement are summarized in Table 1 ¹. Except for (9·2H₂O), which was solved using SIR92 direct methods (Altomare et al., 1994 ), the structures were solved by direct methods using SHELXS97 (Sheldrick, 1990 ) and developed by difference Fourier methods using SHELXL97 (Sheldrick, 1998 ). With the exception of the sp²-bound methyl group in (1), where they were located from a circular difference Fourier synthesis and refined as part of a rigid rotating group, all carbon- and nitrogen-bound H atoms were placed in geometrically calculated positions and refined using riding models (SHELXL97; Sheldrick, 1998). Crystals of (9·2H₂O) are affected by twinning, principally by a 180° rotation about [001] for which the twin fraction was 0.291 (2). The water H atoms in (9·2H₂O) were not located.

Table 1
Experimental table

	(1)	(2)	(3)	(4)	(4·CH₂Cl₂)
Crystal data
Chemical formula	C₅H₆N₂OSe	C₆H₈N₂OSe	C₇H₁₀N₂OSe	C₇H₁₀N₂OSe	C₈H₁₂Cl₂N₂OSe
M_r	189.08	203.10	217.13	217.13	302.06
Cell setting, space group	Monoclinic, P2₁/c	Triclinic, $[P\bar1]$	Orthorhombic, Pbca	Triclinic, $[P\bar1]$	Triclinic, $[P\bar1]$
Temperature (K)	120 (2)	150 (2)	120 (2)	150 (2)	150 (2)
a, b, c (Å)	4.3411 (7), 14.756 (2), 9.690 (2)	8.394 (2), 10.029 (2), 14.931 (4)	10.568 (7), 11.257 (7), 28.79 (2)	8.9192 (9), 10.6403 (10), 15.1965 (15)	8.841 (3), 11.259 (3), 12.424 (4)
α, β, γ (°)	90.00, 90.157 (2), 90.00	101.023 (4), 100.893 (4), 105.705 (4)	90.00, 90.00, 90.00	106.019 (2), 105.366 (2), 96.166 (2)	90.450 (5), 105.350 (4), 92.945 (5)
V (Å³)	620.71 (18)	1148.5 (5)	3425 (4)	1311.0 (2)	1190.7 (6)
Z	4	6	16	6	4
D_x (Mg m^–3)	2.023	1.762	1.684	1.650	1.685
Radiation type	Synchrotron	Mo Kα	Synchrotron	Mo Kα	Mo Kα
No. of reflections for cell parameters	4328	2232	3142	3689	2249
θ range (°)	2.6–29.0	2.6–24.8	2.6–27.5	2.4–27.6	2.4–24.6
μ (mm^–1)	5.96	4.84	4.33	4.24	3.57
Crystal form, colour	Needle, colourless	Triangular prism, colourless	Lath, colourless	Tablet, colourless	Plate, colourless
Crystal size (mm)	0.10 × 0.01 × 0.01	0.21 × 0.12 × 0.04	0.20 × 0.02 × 0.01	0.25 × 0.14 × 0.06	0.36 × 0.22 × 0.02

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer	Bruker SMART APEX CCD area detector	Bruker SMART APEXII CCD diffractometer	Bruker SMART APEX CCD area detector	Bruker SMART APEX CCD area detector
Data collection method	Fine-slice ω scans	ω scans	Fine-slice ω scans	ω scans	ω scans
Absorption correction	Multi-scan (based on symmetry-related measurements)	Multi-scan (based on symmetry-related measurements)	Multi-scan (based on symmetry-related measurements)	Multi-scan (based on symmetry-related measurements)	Multi-scan (based on symmetry-related measurements)
T_min	0.816	0.687	0.260	0.581	0.684
T_max	1.000	1.000	1.000	0.770	1.000
No. of measured, independent and observed reflections	6350, 1770, 1642	8174, 4025, 3189	24 855, 3471, 2417	8163, 5780, 4932	10 743, 6193, 4391
Criterion for observed reflections	I > 2σ(I)	I > 2σ(I)	I > 2σ(I)	I > 2σ(I)	I > 2σ(I)
R_int	0.027	0.038	0.250	0.013	0.050
θ_max (°)	29.0	25.1	25.0	27.6	27.5
Range of h, k, l	–6 → h → 6	–10 → h → 10	–13 → h → 13	–11 → h → 7	–11 → h → 11
	–20 → k → 21	–11 → k → 11	–14 → k → 14	–13 → k → 13	–14 → k → 14
	–13 → l → 13	–17 → l → 17	–35 → l → 35	–17 → l → 19	–16 → l → 16

Refinement
Refinement on	F²	F²	F²	F²	F²
R[F²> 2σ(F²)], wR(F²), S	0.025, 0.074, 0.80	0.056, 0.146, 1.03	0.173, 0.408, 1.18	0.028, 0.071, 1.04	0.052, 0.099, 0.97
No. of reflections	1770	4025	3471	5780	6193
No. of parameters	83	271	99	298	254
H-atom treatment	Rigid rotating group; riding model	Constrained to parent site	Constrained to parent site	Constrained to parent site	Constrained to parent site
Weighting scheme	w = 1/[σ²(F_o²) + (0.079P)²], where P = (F_o² + 2F_c²)/3	w = 1/[σ²(F_o²) + (0.094P)²], where P = (F_o² + 2F_c²)/3	w = 1/[σ²(F_o²) + (0.025P)² + 367.0], where P = (F_o² + 2F_c²)/3	w = 1/[σ²(F_o²) + (0.033P)² + 0.854P], where P = (F_o² + 2F_c²)/3	w = 1/[σ²(F_o²) + (0.0305P)²], where P = (F_o² + 2F_c²)/3
(Δ/σ)_max	0.001	0.001	0.002	0.001	0.001
Δρ_max, Δρ_min (e Å^–3)	0.57, −0.80	1.48, −1.02	2.38, −2.33	0.65, −0.40	0.87, −0.51

	(7)	(9)	(10)	(11)
Crystal data
Chemical formula	C₇H₁₀I₂N₂OSe	C₂₄H₂₆N₈O₄Se₂·2H₂O	C₂₈H₃₄N₈O₄Se₂	C₇H₁₀N₂O₂
M_r	470.93	684.48	704.55	154.17
Cell setting, space group	Triclinic, $[P\bar1]$	Triclinic, $[P\bar1]$	Triclinic, $[P\bar1]$	Rhombohedral, $[R\bar3]$
Temperature (K)	150 (2)	120 (2)	120 (2)	150 (2)
a, b, c (Å)	6.603 (2), 7.700 (3), 13.037 (5)	4.8330 (2), 9.7970 (5), 14.1796 (8)	5.0717 (6), 11.8615 (14), 11.9385 (14)	19.9444 (10), 19.9444 (10), 9.8918 (10)
α, β, γ (°)	75.969 (6), 86.808 (6), 73.113 (6)	83.490 (3), 84.431 (3), 89.353 (3)	83.161 (2), 82.785 (2), 84.358 (2)	90.00, 90.00, 120.00
V (Å³)	615.3 (7)	663.91 (6)	704.90 (14)	3407.6 (10)
Z	2	1	1	18
D_x (Mg m^–3)	2.542	1.712	1.660	1.352
Radiation type	Mo Kα	Mo Kα	Synchrotron	Mo Kα
No. of reflections for cell parameters	1665	2951	1672	1748
θ range (°)	2.8–27.0	2.9–27.5	2.2–27.0	2.4–27.4
μ (mm^–1)	8.04	2.84	2.67	0.10
Crystal form, colour	Column, red	Needle, orange	Plate, colourless	Lens, orange
Crystal size (mm)	0.22 × 0.10 × 0.06	0.20 × 0.04 × 0.03	0.08 × 0.05 × 0.01	0.52 × 0.17 × 0.17

Data collection
Diffractometer	Bruker SMART1000 CCD area detector	Bruker Nonius kappaCCD area detector	Bruker SMART APEXII CCD diffractometer	Bruker SMART APEX CCD area detector
Data collection method	ω scans	ω and φ	Fine-slice ω scans	ω scans
Absorption correction	Multi-scan (based on symmetry-related measurements)	Multi-scan (based on symmetry-related measurements)	Multi-scan (based on symmetry-related measurements)	None
T_min	0.114	0.679	0.804	–
T_max	0.209	1.000	1.000	–
No. of measured, independent and observed reflections	5463, 2660, 1702	13 298, 13 281, 12 058	8292, 4198, 3144	5827, 1750, 1297
Criterion for observed reflections	I > 2σ(I)	I > 2σ(I)	I > 2σ(I)	I > 2σ(I)
R_int	0.061	0.060	0.038	0.039
θ_max (°)	27.5	27.7	28.9	27.5
Range of h, k, l	–8 → h → 8	–6 → h → 6	–7 → h → 7	–25 → h → 19
	–9 → k → 9	–12 → k → 12	–16 → k → 16	–24 → k → 25
	–16 → l → 16	–18 → l → 18	–17 → l → 17	–11 → l → 12

Refinement
Refinement on	F²	F²	F²	F²
R[F²> 2σ(F²)], wR(F²), S	0.038, 0.091, 0.87	0.084, 0.221, 1.04	0.042, 0.097, 0.98	0.044, 0.131, 1.05
No. of reflections	2657	13 281	4198	1750
No. of parameters	118	182	190	100
H-atom treatment	Constrained to parent site	Riding model	Constrained to parent site	Constrained to parent site
Weighting scheme	w = 1/[σ²(F_o²) + (0.048P)²P], where P = (F_o² + 2F_c²)/3	w = 1/[σ²(F_o²) + (0.098P)² + 8.436P], where P = (F_o² + 2F_c²)/3	w = 1/[σ²(F_o²) + (0.0505P)²], where P = (F_o² + 2F_c²)/3	w = 1/[σ²(F_o²) + (0.0725P)²], where P = (F_o² + 2F_c²)/3
(Δ/σ)_max	0.001	0.001	0.001	0.001
Δρ_max, Δρ_min (e Å^–3)	1.26, −1.31	3.35, −2.06	0.59, −0.92	0.45, −0.16
Computer programs used: APEX2 (Bruker, 2004 ), SMART Version 5.625 (Bruker, 2001a ), SMART Version 5.624 (Bruker, 2001a), COLLECT (Hooft, 1998 ), SAINT Version 6.36a (Bruker, 2000 ), DIRAX (Duisenberg, 1992 ), SHELXTL (Bruker, 2001b ), HKL (Otwinowski & Minor, 1997 ), SHELXS97 (Sheldrick, 1990), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 1998), PLATON (Spek, 2003 ), enCIFer (Allen et al., 2004 ).

The structure determination of (3) posed particular difficulties: the crystals were very small in two dimensions (10 and 20 µm) and efforts to obtain a dataset using a sealed X-ray tube or a rotating-anode source gave no significant diffraction. However, we were able to obtain a weak dataset on Station 9.8 of the Daresbury Synchrotron Radiation Source, although even this did not overcome all of the limitations imposed by the poor crystal quality. We found that only the Se atoms could be refined with anisotropic displacement parameters, and a total of 99 geometric, planarity and similarity restraints were necessary for a stable refinement. Although we cannot therefore discuss the fine details of the molecular geometry, it did prove possible to obtain reliable information about the extended structure of (3).

3. Results and discussion

3.1. Molecular structures of (1)–(4), (4·CH₂Cl₂) and (11)

Displacement ellipsoid plots of (1)–(4), (4·CH₂Cl₂) and (11) are shown in Figs. 1 –6 while selected interatomic distances and angles are listed in Tables 2 and 4. Although the asymmetric units of (1) and (11) each comprise single molecules, those of (2), (3), (4) and (4·CH₂Cl₂) comprise three, two, three and two molecules, respectively. The molecular structures of the alkylselenouracils and of 6-n-propyluracil are unremarkable, and the molecular structure of (4) is not affected by recrystallization as (4·CH₂Cl₂) from dichloromethane. The C—Se bond distances in (1)–(4) and in (4·CH₂Cl₂) vary from 1.824 (2) to 1.848 (6) Å (Table 2). The two C=O bond distances found in (11) are almost equal [1.2286 (16), 1.2387 (16) Å; Table 4] and are within the range of the C=O bonds found for other similar compounds such as 1,3-dimethyl-6-R-trisubstituted uracils [R = Me, 1.233 (3) Å; R = Et, 1.224 (2) Å; R = ⁿPr, 1.212 (3), 1.221 (3), 1.220 (3) Å; R = ⁿBu, 1.220 (5), 1.226 (5) Å; Suwinska, 1995 ] and triethylammonium 2,4-dioxo-6-(1,1,2,2,3,3-hexafluoropropyl)-5-benzylsulfonyl-3H-2,4-dihydropyrimidine [1.235 (3), 1.237 (2) Å] (Timoshenko et al., 2002 ).

Table 2
Molecular geometry parameters (Å, °) for (1) (2), (3), (4) and (4·CH₂Cl₂)

(1)		(2)		(3)		(4)		(4·CH₂Cl₂)
Se2—C2	1.832 (2)	Se12—C12	1.835 (6)	Se1—C1	1.837 (16)	Se1—C2	1.843 (2)	Se2—C2	1.829 (6)
N1—C2	1.352 (3)	Se22—C22	1.848 (6)	Se21—C21	1.835 (16)	Se1A—C2A	1.824 (2)	Se12—C12	1.825 (5)
N3—C2	1.353 (3)	Se32—C32	1.828 (7)	N2—C1	1.32 (2)	Se1B—C2B	1.835 (2)	N1—C2	1.345 (7)
O4—C4	1.233 (3)	N11—C12	1.354 (8)	N2—C3	1.40 (2)	N1—C2	1.348 (3)	N3—C2	1.351 (7)
		N21—C22	1.341 (8)	N22—C2	1.39 (2)	N1A—C2A	1.354 (3)	N11—C12	1.355 (7)
Se2—C2—N3	121.99 (16)	N31—C32	1.352 (9)	N6—C1	1.39 (2)	N1B—C2B	1.342 (3)	N13—C12	1.349 (7)
Se2—C2—N1	121.90 (15)	N13—C12	1.352 (7)	N26—C21	1.39 (2)	N1—C6	1.389 (3)	O4—C4	1.232 (7)
		N23—C22	1.349 (7)	O5—C5	1.23 (2)	N1A—C6A	1.383 (3)	O14—C14	1.233 (7)
		N33—C32	1.349 (8)	O25—C25	1.24 (2)	N1B—C6B	1.389 (3)
		O14—C14	1.240 (8)	Se1—C1—N2	123.3 (13)	C2—N3	1.341 (3)	Se2—C2—N1	123.0 (4)
		O24—C24	1.242 (8)	Se1—C1—N6	121.7 (12)	C2A—N3A	1.351 (3)	Se2—C2—N3	121.5 (4)
		O34—C34	1.227 (7)	Se21—C21—N22	123.9 (13)	C2B—N3B	1.353 (3)	Se12—C12—N11	123.5 (4)
				Se21—C21—N26	121.2 (12)	N3—C4	1.400 (3)	Se12—C12—N13	121.1 (4)
		Se12—C12—N11	123.2 (4)			N3A—C4A	1.391 (3)
		Se22—C22—N21	121.0 (4)			N3B—C4B	1.395 (3)
		Se32—C32—N31	123.7 (5)			O1—C4	1.230 (3)
		Se12—C12—N13	121.6 (4)			O1A—C4A	1.237 (3)
		Se22—C22—N23	122.8 (4)			O1B—C4B	1.226 (3)
		Se32—C32—N33	121.3 (5)
						Se1—C2—N1	120.70 (17)
						Se1A—C2A—N1A	123.65 (18)
						Se1B—C2B—N1B	122.91 (17)
						Se1—C2—N3	122.59 (17)
						Se1A—C2A—N3A	121.33 (18)
						Se1B—C2B—N3B	121.19 (17)

Figure 1
Displacement ellipsoid plot of (1) showing the atom-numbering scheme, with ellipsoids drawn at the 50% probability level.

Figure 2
Displacement ellipsoid plot of (2) showing the atom-numbering scheme, with ellipsoids drawn at the 50% probability level. There are three independent molecules in the asymmetric unit.

Figure 3
Displacement ellipsoid plot of (3) showing the atom-numbering scheme, with ellipsoids drawn at the 50% probability level. There are two independent molecules in the asymmetric unit.

Figure 4
Displacement ellipsoid plot of (4) showing the atom-numbering scheme, with ellipsoids drawn at the 50% probability level. There are three independent molecules in the asymmetric unit.

Figure 5
Displacement ellipsoid plot of (4·CH₂Cl₂) showing the atom-numbering scheme, with ellipsoids drawn at the 50% probability level. Two independent molecules of (4) are solvated by two dichloromethane molecules in the asymmetric unit.

Figure 6
Displacement ellipsoid plot of (11) showing the atomic-numbering scheme, with ellipsoids drawn at the 50% probability level.

3.2. Extended structures of (1)–(4), (4·CH₂Cl₂) and (11)

The extended structures formed by the alkylselenouracils are worthy of comment; they depend primarily on hydrogen-bonding interactions between the two N—H donor sites and the oxygen and selenium acceptor sites of the heteroatomic ring [see Scheme (II)]. Pertinent distances and angles associated with the hydrogen-bonding interactions in (1)–(4), (4·CH₂Cl₂) and (11) are included in Table 3.

Table 3
Hydrogen-bonding parameters (Å, °) for (1)–(4), (4·CH₂Cl₂) and (11) [N—H = 0.88 Å; C—H = 0.95 Å; λ = 0.6775 Å for (1), (3) and (10)]

Interaction	H⋯Y (Å)	X⋯Y (Å)	X—H⋯Y (°)
(1)
N1—H1A⋯O4	1.91	2.761 (2)	162
N3—H3A⋯Se2	2.63	3.4825 (14)	162

(2)
N11—H11⋯O34	1.93	2.805 (6)	171
N23—H23⋯O14	1.99	2.868 (7)	172
N31—H31⋯O24	1.97	2.829 (7)	166
N13—H13⋯Se22	2.47	3.340 (5)	169
N21—H21⋯Se22	2.58	3.442 (5)	167
N33—H33⋯Se12	2.55	3.417 (6)	170

(3)
N6—H6N⋯O25	1.96	2.80 (2)	161
N26—H26N⋯O5	1.99	2.84 (2)	162
N2—H2N⋯Se21	2.60	3.44 (2)	160
N22—H22N⋯Se1	2.59	3.46 (2)	167

(4)
N1A—H1AA⋯O1	2.00	2.860 (3)	167
N1B—H1BA⋯O1A	1.92	2.797 (3)	177
N3—H3A⋯O1B	1.91	2.782 (3)	169
N1—H1A⋯Se1	2.60	3.460 (2)	165
N3A—H3AA⋯Se1B	2.60	3.430 (3)	157
N3B—H3BA⋯Se1	2.56	3.428 (2)	167

(4·CH₂Cl₂)
N3—H3⋯O14	1.97	2.831 (6)	167
N13—H13⋯O4	1.98	2.854 (6)	172
N1—H1⋯Se12	2.55	3.424 (5)	175
N11—H11⋯Se2	2.57	3.448 (5)	176
C21—H21A⋯O4	2.34	3.230 (7)	150

(11)
N1—H1A⋯O4	1.91	2.771 (2)	166
N3—H3A⋯O2	2.01	2.856 (2)	161
C9—H9A⋯O4	2.52	3.491 (2)	169

Analysis of the hydrogen-bonding parameters in these compounds confirms a range of intermolecular contacts with similar numbers of N1—H⋯O and N3—H⋯O and of N1—H⋯Se and N3—H⋯Se interactions.

The extended structure of (1) is a two-dimensional sheet of topology 6³ (Fig. 7). A centrosymmetrically related pair of N3—H⋯Se contacts form an R₂²(8) ring which links two molecules, thereby forming a dimeric unit. Each dimeric unit is bridged to four adjacent dimeric units through four single N1—H⋯O contacts to give a sheet of six-membered rings, each of which involves an R₆⁶(28) hydrogen-bonded motif (Table 3). The 6³ topology of the sheet, which is aligned parallel to the ( $[10\bar2]$ ) plane, results in a brick-wall architecture (Fig. 7).

Figure 7
View of part of a sheet in the crystal structure of (1) showing the intermolecular N—H⋯O and pairwise N—H⋯Se interactions. Atoms are identified as follows: Se, large cross-hatched circles; O, hatched circles; N, dotted circles; C, intermediate open circles; H, small open circles.

The extended structures of (2) and (4) are analogous. They crystallize in the same space group with similar cell dimensions, the only difference being the alkyl group. Their extended structure (Fig. 8) is based on a chain of eight-membered rings which is aligned in the [101] direction in the ( $[21\bar2]$ ) plane. The three molecules in the asymmetric unit are involved in different hydrogen-bonding motifs; the first (numbered C11 etc.) acts as a two-donor one-acceptor (2D–1A) species; the second (numbered C21 etc.) acts as a two-donor three-acceptor species (2D–3A); the third (numbered C31 etc.) acts as a two-donor two-acceptor species (2D–2A). Each eight-membered ring is centrosymmetric and comprises two 2D–1A molecules, two 2D–2A molecules and four 2D–3A molecules. Pairs of centrosymmetrically related 2D–3A molecules are common to two adjacent rings, thereby giving the correct stoichiometry. The hydrogen-bonding interactions leading to the eight-membered ring comprise an R₈⁶(32) motif (Table 3). The aliphatic residues of the two 2D–1A and two 2D–2A molecules are located on the edges of the chain, preventing inter-chain hydrogen-bond formation (Fig. 8).

Figure 8
View of part of a sheet in the crystal structure of (2) showing the intermolecular N—H⋯O and N—H⋯Se interactions. Atoms are identified as in Fig. 7

In (3), R₂²(8) hydrogen-bonding motifs link the two molecules of the asymmetric unit, which alternate along the b axis to form a one-dimensional chain (Fig. 9). The R₂²(8) motifs differ in that one has oxygen acceptors and the other has selenium acceptors. The 1:1 adduct (4·CH₂Cl₂) has a similar extended structure (Fig. 10) to that of (3). In this case, however, the chain is aligned along the b axis. One of the dichloromethane molecules is locked in position by a relatively short C—H⋯O contact (Table 3).

Figure 9
View of part of a chain in the crystal structure of (3) showing the intermolecular N—H⋯O and N—H⋯Se interactions. Atoms are identified as in Fig. 7

Figure 10
View of part of a chain in the crystal structure of (4·CH₂Cl₂) showing the intermolecular N—H⋯O and N—H⋯Se interactions. Atoms are identified as in Fig. 7

It is interesting to note that a different extended structure is adopted by 6-n-propyluracil (11), the uracil corresponding to (3). The asymmetric unit of (11) comprises a single molecule (Fig. 6), six of which combine to form a six-membered ring (Fig. 11). Linking each pair of molecules is an R₂²(8) hydrogen-bonding motif, which forms part of the R₆⁶(24) hydrogen-bonding motif (Table 3), generating the inner diameter of the six-membered ring. The rings assemble on a sheet parallel to the (001) plane. The only inter-ring interactions are a centrosymmetric pair of relatively long C—H⋯O contacts between the pendant CH₃ groups and carbonyl O atoms (Table 3). Six-membered ring formation is possible owing to the fact that the R₂²(8) motifs in (11) [see Scheme (IIIa)], which comprise two N—H⋯O contacts, are symmetrical and generate an internal ring angle of 120°. If (3) were to adopt a similar structure, the corresponding R₂²(8) motifs would be unsymmetrical as they would comprise one short N—H⋯O contact and one long N—H⋯Se contact. Analysis of the structure of (2), which contains such assemblies, gives a value of 133° for the internal ring angle [see Scheme (IIIb)], which does not permit ring formation as it falls between the values required for seven- and eight-membered rings, namely 128.6 and 135°, respectively. Hence, (3) adopts a one-dimensional chain architecture with alternating R₂²(8) rings with pairs of oxygen and selenium acceptors (Fig. 9).

Figure 11
View of part of a sheet of (11) showing the intermolecular N—H⋯O interactions. Atoms are identified as in Fig. 7

3.3. Molecular structures of (7), (9·2H₂O) and (10)

Displacement ellipsoid plots of compounds (7), (9·2H₂O) and (10) are shown in Figs. 12, 13 and 14, while their selected bond lengths and angles are listed in Table 4. Compound (7) exhibits the so-called `spoke' structure typical of iodine adducts of selenium-containing compounds. The I—Se—C—N torsion angles [−0.5 (6)° and −179.3 (6)° for (7)], together with the C—Se—I and Se—I—I angles (Table 4), are consistent with a planar arrangement. This planarity, which is typical of charge-transfer complexes with a `spoke' structure, is enhanced by an intramolecular N—H⋯I hydrogen bond between N3 and I1 (Table 5; Fig. 15).

Table 4
Molecular geometry parameters (Å, °) for (7), (9·2H₂O), (10) and (11)

(7)		(9·2H₂O)		(10)		(11)
I1—I2	2.8928 (10)	Se2—Se2	2.4328 (9)	Se2—Se2	2.4427 (6)	O2—C2	1.2286 (16)
I1—Se	2.7807 (11)	Se2—C2	1.925 (4)	Se2—C2	1.922 (4)	O4—C4	1.2387 (16)
Se—C2	1.876 (6)	N1—C2	1.283 (6)	N1—C2	1.296 (4)	N1—C2	1.3668 (15)
N1—C2	1.331 (8)	N3—C2	1.412 (6)	N3—C2	1.407 (4)	N3—C2	1.3653 (14)
N3—C2	1.334 (8)	N3—C4	1.431 (6)	N3—C4	1.421 (3)	N3—C4	1.3895 (12)
N3—C4	1.405 (8)	O4—C4	1.233 (5)	O4—C4	1.236 (4)
O4—C4	1.213 (8)	N3—C12	1.420 (5)	N3—C12	1.436 (4)	O2—C2—N3	122.39 (11)
		N11—C12	1.296 (4)	N11—C12	1.271 (4)	O2—C2—N1	122.45 (11)
I2—I1—Se	176.75 (2)	N13—C12	1.337 (3)	N13—C12	1.356 (4)	O4—C4—N3	119.56 (11)
I1—Se—C2	96.9 (2)	N13—C14	1.400 (3)	N13—C14	1.396 (4)	O4—C4—C5	125.10 (9)
		O14—C14	1.232 (3)	O14—C14	1.230 (4)	N1—C2—N3	115.15 (8)
		Se2—Se2—C2	88.99 (14)	Se2—Se2—C2	89.44 (8)
		Se2—C2—N1	114.7 (3)	Se2—C2—N1	122.2 (2)
		Se2—C2—N3	121.6 (3)	Se2—C2—N3	115.1 (2)

		C2—Se2—Se2—C2	−179.98 (18)	C2—Se2—Se2—C2	180

Table 5
Hydrogen-bonding parameters (Å, °) for (7), (9·2H₂O) and (10) (N—H = 0.88 Å; C—H = 0.95 Å)

Interaction	H⋯Y (Å)	X⋯Y (Å)	X—H⋯Y (°)
(7)
N1—H1N⋯O4	1.85	2.698 (8)	161
N3—H3N⋯I1	2.66	3.371 (5)	139

(9·2H₂O)
N13—H13A⋯O4	1.88	2.560 (5)	133
N13—H13A⋯O4′	2.36	3.166 (5)	152
C5—H5A⋯O14	2.48	3.304 (5)	145
O1⋯O14		2.861 (5)
O1⋯O1′		2.741 (5)
O1⋯O1′		2.770 (5)

(10)
N13—H13A⋯O4	1.84	2.534 (3)	134
C5—H5A⋯O4	2.59	3.535 (4)	176
C15—H15A⋯O14	2.61	3.562 (4)	175

Figure 12
Displacement ellipsoid plot of (7) showing the atom-numbering scheme, with ellipsoids drawn at the 50% probability level.

Figure 13
Displacement ellipsoid plot of molecule (9·2H₂O) showing the atomic-numbering scheme, with ellipsoids drawn at the 50% probability level. The diselenide link is formed between Se2 and its symmetry equivalent at (1 − x, −y, 1 − z). The water H atoms were not located.

Figure 14
Displacement ellipsoid plot of molecule (10) showing the atomic-numbering scheme, with ellipsoids drawn at the 50% probability level. The diselenide link is formed between Se2 and its symmetry equivalent at (−x, −y, −z).

Figure 15
View of part of a chain in the crystal structure of (7) showing the intermolecular N—H⋯O and C—H⋯I and Se⋯I interactions. Atoms are identified as in Fig. 7

The I—I interatomic distance of 2.8928 (10) Å in (7) is longer than that in either the gas phase (2.677 Å: Pauling, 1960 ) or crystalline diiodine [2.715 (6) Å at 110 K: van Bolhuis et al., 1967 ], presumably owing to the Se⋯I interaction. It is, however, the shortest such distance measured for a diiodine–selenoamide complex (Antoniadis et al., 2006) suggesting minimal perturbation resulting from the long Se⋯I contact. Interestingly, correlation of the available Se⋯I and I⋯I distance data (see Antoniadis et al., 2006) shows there to be a linear relationship between the two, which is quantified by the expression: d(Se⋯I) = −0.7981d(I⋯I) + 5.0983, R² = 0.9805. The I—I bond order of 0.547 calculated for (7) using the expression of Pauling (1960) is the highest such bond order for selenoamide–diiodine complexes. All these data are consistent with a very weak Se⋯I interaction. Bigoli et al. (1996 , 1999 ) have separated iodine adducts of sulfur donors into three classes on the basis of I⋯I bond order. Applying the same criteria to iodine adducts of selenium donors, (7) falls into the intermediate, rather than the weakest, classification which would require an I⋯I distance of 3.92 Å, which is close to double the van der Waals radius of iodine (1.98 Å). Therefore, a third type of Se—I adduct seems very unlikely. Although the C—Se distance in (7) [1.876 (6) Å] is slightly longer than that for the corresponding free selenouracil (3) [average 1.836 (11) Å; Table 2], it is similar to the C—Se distances found for the other charge-transfer complexes (see Antoniadis et al., 2006).

Re-crystallization of (6) and (7) from acetone solutions results in the formation of the diselenides (9·2H₂O) and (10), respectively [see Scheme (I)]. Their molecular structures consist of two centrosymmetrically related selenoamide ligands, which have been N-substituted by a deselenated ligand molecule, linked through an Se—Se bond to form the diselenide (Figs. 13 and 14). The presence of a crystallographic inversion centre between the selenoamides fixes the C—Se—Se—C torsion angle at 180°, which is unusual for diselenoamides. The majority of those listed have torsion angles between 50 and 93°, the only other example of a 180° angle being that in N,N,N′,N′-tetraethylthiuramdiselenide (Dietzsch et al., 1998 ).

The Se—Se bond distances in (9·2H₂O) [2.4328 (9) Å] and (10) [2.4427 (6) Å] fall within the range observed in other diselenoamides (2.34–2.59 Å; Antoniadis et al., 2006). The C—Se bond lengths in (9·2H₂O) [1.925 (4) Å] and (10) [1.922 (4) Å], although longer than those of the corresponding free ligands (2) [mean C—Se 1.838 (5) Å] and (3) [mean C—Se 1.836 (11) Å], fall in the range of other such compounds (1.874−1.952 Å; Antoniadis et al., 2006). Molecules (9·2H₂O) and (10) are neutral diselenoamides with two unequal C—N bond distances, as expected for such compounds. These bond distances become equal in the case of ionic diselenoamides. The Se—Se—C bond angles in (9·2H₂O) [88.99 (14)°] and (10) [89.44 (8)°] are at the lower end of the range found for diselenoamides.

3.4. Extended structures of (7), (9·2H₂O) and (10)

The extended structure of (7) is based on a linear chain aligned along the b axis (Fig. 15). The principal contact between adduct molecules is an intermolecular N—H⋯O hydrogen bond (Table 5). It is supported by an interaction between the terminal iodine and the selenium atom [Se⋯I2 (x − 1, y, z) 3.862 (2) Å; I1—I2⋯Se (1 + x, y, z) 87.02 (3); C2—Se⋯I2 (x − 1, y, z) 171.3 (2); I1—Se⋯I2 (x − 1, y, z) 83.82 (3); C2—Se⋯I1 96.9 (2)°].

The extended structures of (9·2H₂O) and (10) are similar. They form chains aligned along the [210] and [101] directions, respectively, as shown in Figs. 16 and 17, respectively. The principal links between molecules in (9·2H₂O) are N—H⋯O and in (10) are C—H⋯O hydrogen bonds. The reason for the difference is not clear. In the case of (9·2H₂O), the N—H⋯O contact is quite long at 3.166 (5) Å, and by inference weak, owing to bifurcation of the hydrogen bond, the other contact being an intramolecular interaction of 2.560 (5) Å. The intermolecular contact is supported by a relatively short C—H⋯O hydrogen bond [C⋯O 3.304 (5) Å]. In the case of (10), the N—H⋯O intramolecular contact [N⋯O 2.534 (3) Å] is an independent interaction, the molecules being linked by a pair of centrosymmetrically related, somewhat long, C—H⋯O hydrogen bonds [C⋯O 3.535 (4) Å] which form an R₂²(8) motif (Fig. 17).

Figure 16
View of part of a sheet of (9·2H₂O) showing the inter- and intramolecular N—H⋯O and intermolecular C—H⋯O interactions. Atoms are identified as in Fig. 7

Figure 17
View of part of a sheet of (10) showing the intramolecular N—H⋯O and intermolecular C—H⋯O interactions. Atoms are identified as in Fig. 7

In both structures the chains are stacked to give two-dimensional sheet architectures parallel to ( $[1\bar20]$ ) for (9·2H₂O) and to ( $[\bar121]$ ) for (10). In the case of (9·2H₂O) the chains are linked through hydrogen-bonded water molecules which not only form the sheet but also link the sheets into a three-dimensional structure. Although it was not possible to locate the water H atoms, the proposed interactions are supported by the geometries around the O atoms. Thus, O⋯O distances range from 2.741 (5) through 2.770 (5) to 2.861 (5) Å, while O⋯O⋯O angles range from 109.9 (2) through 122.5 (3) to 123.7 (2)°. There are no aromatic stacking interactions owing to a staggered molecular arrangement. The only other possible interaction linking the sheets is an Se⋯Se contact, but the interatomic distance is extremely long [4.125 (2) Å]. In the case of (10) the chains are linked into two-dimensional sheets by relatively long C—H⋯O contacts [C⋯O 3.562 (4) Å; Table 5]. Hydrogen-bonded contacts between sheets are not feasible and the staggered molecular arrangement precludes aromatic stacking interactions. The only possible interaction is an Se⋯Se contact, but the interatomic distance of 3.961 (2) Å is rather long.

4. Concluding remarks

The architectures of the extended structures of the 6-alkyl-2-selenouracils (1)–(4) and (4·CH₂Cl₂) rely heavily on R₂²(8) hydrogen-bonded rings. All three types of rings, namely those based on two oxygen acceptors [O/O; see Scheme (IVa)], two selenium acceptors [Se/Se; see Scheme (IVb)] and a mixture of one oxygen and one selenium acceptor [O/Se; see Scheme (IVc)], are found in the 6-alkyl-2-selenouracils. The most common is the Se/Se ring; it appears in the extended structures of all five compounds [(1)–(4) and (4·CH₂Cl₂)]. The other two types of ring appear twice only, the O/O ring in (3) and (4·CH₂Cl₂) and the O/Se ring in (2) and (4). The simplest structures are those of (3) and (4·CH₂Cl₂), where alternating Se/Se and O/O rings give rise to one-dimensional chain constructs (Figs. 9 and 10). In (1), Se/Se rings form dimers which are linked through N—H⋯O hydrogen bonds to give a two-dimensional sheet of topology 6³ (Fig. 7). In (2) and (4), Se/Se and O/Se rings alternate to form chains of 6-alkyl-2-selenouracils, which are linked through N—H⋯O hydrogen bonds to give a two-dimensional sheet (Fig. 8). O/O R₂²(8) hydrogen-bonded rings are also found in the extended structure of 6-n-propyl-2-uracil (11), where they generate a six-membered paddle-wheel ring with pendant propyl groups (Fig. 11).

The extended structures of the diselenide oxidation products (9·2H₂O and 10) also depend on O/O R₂²(8) hydrogen-bonded rings. However, in (9·2H₂O) the donors are a mixture of C—H and N—H moieties [see (IVd)] while in (10) they are exclusively C—H donors. In both cases the molecules are linked to give rise to chain architectures (Figs. 16 and 17).

The O atoms of all five 6-alkyl-2-selenouracil and of the single 6-n-propyl-2-uracil structures act as acceptors to just one hydrogen-bonded contact. The Se atoms behave similarly except in (2) and (4). Of the Se atoms of the three molecules in the asymmetric unit of (2) and (4), one acts as a dual acceptor, one as a single acceptor while the third is not involved in any hydrogen bonds (Fig. 8). The situation in the oxidation products (9·2H₂O and 10) is complicated by the existence of intramolecular N—H⋯O hydrogen bonds. In (9·2H₂O) one oxygen acts as a dual acceptor to intra- and intermolecular N—H⋯O hydrogen bonds and a second oxygen acts as a single acceptor in an intermolecular C—H⋯O hydrogen bond. All three contacts generate the one-dimensional chain structure (Fig. 16). In (10), one oxygen acts as a dual acceptor to an intramolecular N—H⋯O and an intermolecular C—H⋯O hydrogen bond to generate the one-dimensional chain structure, while a second oxygen acts as a single acceptor in an interchain C—H⋯O hydrogen bond (Fig. 17).

Supporting information

Crystal structure: contains datablocks 1, 2, 3, 4, 4.CH2Cl2, 7, 9, 10, 11. DOI: 10.1107/S0108768106011426/so5003sup1.cif

Structure factors: contains datablock sepmme. DOI: 10.1107/S0108768106011426/so50031sup2.hkl

Structure factors: contains datablock etseno. DOI: 10.1107/S0108768106011426/so50032sup3.hkl

Structure factors: contains datablock sepmon. DOI: 10.1107/S0108768106011426/so50033sup4.hkl

Structure factors: contains datablock iprsen. DOI: 10.1107/S0108768106011426/so50034sup5.hkl

Structure factors: contains datablock i2mseu. DOI: 10.1107/S0108768106011426/so50034.CH2Cl2sup6.hkl

Structure factors: contains datablock i2sepr. DOI: 10.1107/S0108768106011426/so50037sup7.hkl

Structure factors: contains datablock etse2i_t. DOI: 10.1107/S0108768106011426/so50039sup8.hkl

Structure factors: contains datablock sepmoi. DOI: 10.1107/S0108768106011426/so500310sup9.hkl

Structure factors: contains datablock i2prse. DOI: 10.1107/S0108768106011426/so500311sup10.hkl

Computing details top

Data collection: Bruker APEX2 (Bruker, 2004) for (1), (3); Bruker SMART version 5.625 (Bruker, 2001) for (2), (4), 4.CH2Cl2, (11); Bruker SMART version 5.624 (Bruker, 2001) for (7); COLLECT (Hooft, 1998) for (9); Bruker APEX2 for (10). Cell refinement: Bruker SAINT (Bruker, 2004) for (1), (3); Bruker SAINT version 6.36a (Bruker, 2000) for (2), (4), 4.CH2Cl2, (11); Bruker SAINT version 6.36a (Bruker, 2001) for (7); DIRAX (Duisenberg, 1992) for (9); Bruker SAINT for (10). Data reduction: Bruker SAINT for (1), (3); Bruker SAINT; Bruker SHELXTL (Bruker, 2001) for (2), (4), 4.CH2Cl2, (11); Bruker SAINT; Bruker SHELXTL for (7), (10); HKL (Otwinowski & Minor, 1997) for (9). Program(s) used to solve structure: SHELXS97 (Sheldrick, 1990) for (1), (2), (3), (4), 4.CH2Cl2, (7), (10), (11); SIR92 (Altomare et al., 1994) for (9). For all compounds, program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003). Software used to prepare material for publication: enCIFer (Allen et al., 2004); PLATON for (1), (2), (3), (4), 4.CH2Cl2, (9), (10), (11); enCIFer (Allen et al., 2004; PLATON) for (7).

Figures top

(1) top

Crystal data top

C₅H₆N₂OSe	F(000) = 368
M_r = 189.08	D_x = 2.023 Mg m⁻³
Monoclinic, P2₁/c	Synchrotron radiation, λ = 0.6775 Å
a = 4.3411 (7) Å	Cell parameters from 4328 reflections
b = 14.756 (2) Å	θ = 2.6–29.0°
c = 9.690 (2) Å	µ = 5.96 mm⁻¹
β = 90.157 (2)°	T = 120 K
V = 620.71 (18) Å³	Needle, colourless
Z = 4	0.10 × 0.01 × 0.01 mm

Data collection top

Bruker SMART APEXII CCD diffractometer	1770 independent reflections
Radiation source: Daresbury Laboratory Station 9.8	1642 reflections with I > 2σ(I)
Silicone (111) monochromator	R_int = 0.027
fine–slice ω scans	θ_max = 29.0°, θ_min = 4.0°
Absorption correction: multi-scan (SADABS version 2.10; Bruker, 2003)	h = −6→6
T_min = 0.816, T_max = 1.000	k = −20→21
6350 measured reflections	l = −13→13

Refinement top

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)] = 0.025	Hydrogen site location: methyl H atoms from delta-F; others placed geometrically
wR(F²) = 0.074	Rigid rotating group; riding model
S = 0.80	w = 1/[σ²(F_o²) + (0.079P)²] where P = (F_o² + 2F_c²)/3
1770 reflections	(Δ/σ)_max = 0.001
83 parameters	Δρ_max = 0.57 e Å⁻³
0 restraints	Δρ_min = −0.80 e Å⁻³

Crystal data top

C₅H₆N₂OSe	V = 620.71 (18) Å³
M_r = 189.08	Z = 4
Monoclinic, P2₁/c	Synchrotron radiation, λ = 0.6775 Å
a = 4.3411 (7) Å	µ = 5.96 mm⁻¹
b = 14.756 (2) Å	T = 120 K
c = 9.690 (2) Å	0.10 × 0.01 × 0.01 mm
β = 90.157 (2)°

Data collection top

Bruker SMART APEXII CCD diffractometer	1770 independent reflections
Absorption correction: multi-scan (SADABS version 2.10; Bruker, 2003)	1642 reflections with I > 2σ(I)
T_min = 0.816, T_max = 1.000	R_int = 0.027
6350 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.025	0 restraints
wR(F²) = 0.074	Rigid rotating group; riding model
S = 0.80	Δρ_max = 0.57 e Å⁻³
1770 reflections	Δρ_min = −0.80 e Å⁻³
83 parameters

Special details top

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

	x	y	z	U_iso*/U_eq
N1	0.2422 (3)	0.73923 (8)	0.10993 (12)	0.0105 (2)
H1A	0.3737	0.7485	0.1777	0.013*
C2	0.1605 (3)	0.65292 (9)	0.08020 (14)	0.0104 (2)
Se2	0.32333 (3)	0.556089 (10)	0.173603 (14)	0.01181 (9)
N3	−0.0470 (3)	0.64228 (8)	−0.02297 (12)	0.0116 (2)
H3A	−0.1048	0.5866	−0.0428	0.014*
C4	−0.1767 (3)	0.71205 (9)	−0.10027 (15)	0.0119 (3)
O4	−0.3644 (3)	0.69250 (9)	−0.19136 (13)	0.0180 (2)
C5	−0.0765 (3)	0.80120 (9)	−0.06473 (15)	0.0119 (2)
H5A	−0.1540	0.8521	−0.1139	0.014*
C6	0.1301 (3)	0.81340 (9)	0.03956 (14)	0.0111 (2)
C7	0.2429 (3)	0.90396 (9)	0.08536 (16)	0.0153 (3)
H7D	0.2201	0.9475	0.0097	0.023*
H7A	0.4606	0.8995	0.1116	0.023*
H7B	0.1223	0.9243	0.1648	0.023*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0136 (5)	0.0082 (5)	0.0097 (5)	−0.0003 (4)	−0.0031 (4)	−0.0010 (4)
C2	0.0119 (5)	0.0100 (6)	0.0093 (6)	0.0011 (4)	−0.0006 (4)	0.0007 (4)
Se2	0.01526 (13)	0.00869 (12)	0.01146 (12)	0.00109 (4)	−0.00368 (7)	0.00126 (4)
N3	0.0137 (5)	0.0089 (5)	0.0123 (5)	−0.0014 (4)	−0.0043 (4)	0.0003 (4)
C4	0.0126 (6)	0.0115 (6)	0.0116 (6)	0.0009 (5)	−0.0018 (5)	0.0011 (5)
O4	0.0203 (5)	0.0170 (6)	0.0165 (5)	−0.0005 (4)	−0.0106 (4)	0.0005 (4)
C5	0.0140 (6)	0.0100 (6)	0.0116 (6)	0.0008 (5)	−0.0032 (5)	0.0014 (5)
C6	0.0135 (6)	0.0089 (6)	0.0108 (6)	0.0005 (4)	−0.0005 (5)	−0.0001 (4)
C7	0.0198 (7)	0.0093 (6)	0.0169 (7)	−0.0004 (5)	−0.0052 (5)	−0.0013 (5)

Geometric parameters (Å, º) top

N1—C2	1.3528 (17)	C4—C5	1.427 (2)
N1—C6	1.3776 (17)	C5—C6	1.361 (2)
N1—H1A	0.8800	C5—H5A	0.9500
C2—N3	1.3531 (18)	C6—C7	1.4904 (19)
C2—Se2	1.8322 (14)	C7—H7D	0.9800
N3—C4	1.3913 (18)	C7—H7A	0.9800
N3—H3A	0.8800	C7—H7B	0.9800
C4—O4	1.2338 (18)

C2—N1—C6	123.40 (12)	C6—C5—C4	120.05 (13)
C2—N1—H1A	118.3	C6—C5—H5A	120.0
C6—N1—H1A	118.3	C4—C5—H5A	120.0
N1—C2—N3	116.12 (12)	C5—C6—N1	119.57 (12)
N1—C2—Se2	121.90 (10)	C5—C6—C7	123.70 (13)
N3—C2—Se2	121.98 (10)	N1—C6—C7	116.72 (12)
C2—N3—C4	125.41 (12)	C6—C7—H7D	109.5
C2—N3—H3A	117.3	C6—C7—H7A	109.5
C4—N3—H3A	117.3	H7D—C7—H7A	109.5
O4—C4—N3	118.52 (13)	C6—C7—H7B	109.5
O4—C4—C5	126.04 (14)	H7D—C7—H7B	109.5
N3—C4—C5	115.44 (13)	H7A—C7—H7B	109.5

(2) top

Crystal data top

C₆H₈N₂OSe	Z = 6
M_r = 203.10	F(000) = 600
Triclinic, P1	D_x = 1.762 Mg m⁻³
a = 8.394 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.029 (2) Å	Cell parameters from 2232 reflections
c = 14.931 (4) Å	θ = 2.7–24.8°
α = 101.023 (4)°	µ = 4.84 mm⁻¹
β = 100.893 (4)°	T = 150 K
γ = 105.705 (4)°	Triangular prism, colourless
V = 1148.5 (5) Å³	0.21 × 0.12 × 0.04 mm

Data collection top

Bruker SMART APEX CCD area detector diffractometer	4025 independent reflections
Radiation source: normal-focus sealed tube	3189 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
ω scans	θ_max = 25.1°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS version 2.03; Bruker, 2001)	h = −10→10
T_min = 0.687, T_max = 1.000	k = −11→11
8174 measured reflections	l = −17→17

Refinement top

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.146	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.094P)²] where P = (F_o² + 2F_c²)/3
4025 reflections	(Δ/σ)_max = 0.001
271 parameters	Δρ_max = 1.48 e Å⁻³
69 restraints	Δρ_min = −1.02 e Å⁻³

Crystal data top

C₆H₈N₂OSe	γ = 105.705 (4)°
M_r = 203.10	V = 1148.5 (5) Å³
Triclinic, P1	Z = 6
a = 8.394 (2) Å	Mo Kα radiation
b = 10.029 (2) Å	µ = 4.84 mm⁻¹
c = 14.931 (4) Å	T = 150 K
α = 101.023 (4)°	0.21 × 0.12 × 0.04 mm
β = 100.893 (4)°

Data collection top

Bruker SMART APEX CCD area detector diffractometer	4025 independent reflections
Absorption correction: multi-scan (SADABS version 2.03; Bruker, 2001)	3189 reflections with I > 2σ(I)
T_min = 0.687, T_max = 1.000	R_int = 0.038
8174 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	69 restraints
wR(F²) = 0.146	H-atom parameters constrained
S = 1.03	Δρ_max = 1.48 e Å⁻³
4025 reflections	Δρ_min = −1.02 e Å⁻³
271 parameters

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
N11	0.3293 (6)	0.8677 (5)	1.0200 (3)	0.0162 (10)
H11	0.3777	0.8461	1.0705	0.019*
C12	0.2680 (7)	0.9799 (6)	1.0320 (4)	0.0170 (12)
Se12	0.27048 (8)	1.08298 (6)	1.14818 (4)	0.0202 (2)
N13	0.2027 (6)	1.0113 (5)	0.9517 (3)	0.0183 (11)
H13	0.1618	1.0836	0.9583	0.022*
C14	0.1931 (8)	0.9420 (7)	0.8602 (4)	0.0198 (13)
O14	0.1350 (6)	0.9862 (5)	0.7932 (3)	0.0254 (10)
C15	0.2547 (8)	0.8195 (6)	0.8531 (4)	0.0194 (13)
H15	0.2494	0.7635	0.7929	0.023*
C16	0.3197 (8)	0.7852 (6)	0.9323 (4)	0.0186 (13)
C17	0.3885 (8)	0.6621 (6)	0.9367 (5)	0.0218 (14)
H17A	0.3284	0.6041	0.9742	0.026*
H17B	0.5112	0.7013	0.9706	0.026*
C18	0.3707 (9)	0.5628 (7)	0.8409 (5)	0.0286 (16)
H18A	0.4180	0.4859	0.8508	0.043*
H18B	0.4334	0.6179	0.8037	0.043*
H18C	0.2495	0.5211	0.8069	0.043*
N21	0.9297 (6)	0.4151 (5)	0.8474 (3)	0.0188 (11)
H21	0.9349	0.4819	0.8967	0.023*
Se22	1.10728 (8)	0.31656 (6)	0.98373 (4)	0.0199 (2)
C22	1.0003 (7)	0.3140 (6)	0.8630 (4)	0.0163 (12)
N23	0.9863 (7)	0.2112 (5)	0.7863 (3)	0.0185 (11)
H23	1.0347	0.1454	0.7947	0.022*
C24	0.9002 (8)	0.2019 (7)	0.6944 (4)	0.0225 (14)
O24	0.8883 (6)	0.0990 (5)	0.6294 (3)	0.0299 (11)
C25	0.8338 (8)	0.3177 (6)	0.6841 (4)	0.0217 (14)
H25	0.7783	0.3210	0.6233	0.026*
C26	0.8502 (8)	0.4215 (6)	0.7606 (4)	0.0192 (13)
C27	0.7818 (9)	0.5460 (7)	0.7603 (4)	0.0248 (14)
H27A	0.6857	0.5315	0.7908	0.030*
H27B	0.8730	0.6344	0.7995	0.030*
C28	0.7202 (12)	0.5692 (9)	0.6649 (5)	0.048 (2)
H28A	0.6788	0.6521	0.6724	0.072*
H28B	0.6268	0.4838	0.6258	0.072*
H28C	0.8147	0.5867	0.6344	0.072*
N31	0.7033 (7)	0.9832 (5)	0.4380 (4)	0.0222 (12)
H31	0.7555	1.0315	0.4968	0.027*
C32	0.6233 (8)	1.0491 (7)	0.3819 (4)	0.0233 (14)
Se32	0.62624 (11)	1.23434 (7)	0.41986 (5)	0.0368 (2)
N33	0.5403 (7)	0.9682 (5)	0.2936 (4)	0.0212 (12)
H33	0.4826	1.0070	0.2566	0.025*
O34	0.4622 (6)	0.7690 (4)	0.1719 (3)	0.0266 (11)
C34	0.5370 (8)	0.8274 (6)	0.2550 (4)	0.0216 (14)
C35	0.6296 (8)	0.7701 (6)	0.3200 (4)	0.0221 (14)
H35	0.6351	0.6762	0.2993	0.027*
C36	0.7090 (8)	0.8454 (6)	0.4098 (4)	0.0203 (13)
C37	0.8074 (9)	0.7937 (7)	0.4832 (4)	0.0259 (15)
H37A	0.7522	0.7931	0.5362	0.031*
H37B	0.9247	0.8627	0.5081	0.031*
C38	0.8198 (10)	0.6442 (7)	0.4475 (5)	0.0326 (17)
H38A	0.8854	0.6184	0.4993	0.049*
H38B	0.8774	0.6441	0.3962	0.049*
H38C	0.7045	0.5744	0.4242	0.049*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N11	0.020 (3)	0.010 (2)	0.018 (3)	0.008 (2)	0.002 (2)	0.002 (2)
C12	0.017 (3)	0.009 (3)	0.024 (3)	0.003 (2)	0.003 (2)	0.003 (2)
Se12	0.0299 (4)	0.0105 (3)	0.0217 (4)	0.0122 (3)	0.0052 (3)	0.0006 (2)
N13	0.025 (3)	0.010 (3)	0.022 (3)	0.010 (2)	0.004 (2)	0.002 (2)
C14	0.022 (3)	0.016 (3)	0.022 (3)	0.008 (3)	0.007 (3)	0.003 (3)
O14	0.041 (3)	0.020 (2)	0.023 (2)	0.020 (2)	0.009 (2)	0.0068 (19)
C15	0.029 (3)	0.008 (3)	0.022 (3)	0.009 (3)	0.007 (3)	0.000 (2)
C16	0.023 (3)	0.010 (3)	0.025 (3)	0.006 (3)	0.011 (3)	0.003 (2)
C17	0.023 (3)	0.011 (3)	0.032 (4)	0.011 (3)	0.004 (3)	0.003 (3)
C18	0.044 (4)	0.010 (3)	0.036 (4)	0.017 (3)	0.012 (3)	0.000 (3)
N21	0.031 (3)	0.010 (3)	0.015 (2)	0.012 (2)	0.003 (2)	−0.002 (2)
Se22	0.0325 (4)	0.0099 (3)	0.0178 (3)	0.0130 (3)	0.0012 (3)	0.0009 (2)
C22	0.017 (3)	0.010 (3)	0.020 (3)	0.003 (2)	0.003 (2)	0.004 (2)
N23	0.031 (3)	0.008 (2)	0.019 (2)	0.013 (2)	0.004 (2)	0.002 (2)
C24	0.036 (4)	0.017 (3)	0.017 (3)	0.012 (3)	0.007 (3)	0.003 (2)
O24	0.053 (3)	0.016 (2)	0.023 (2)	0.022 (2)	0.004 (2)	0.0002 (19)
C25	0.036 (4)	0.016 (3)	0.017 (3)	0.016 (3)	0.005 (3)	0.006 (2)
C26	0.027 (3)	0.014 (3)	0.021 (3)	0.011 (3)	0.007 (3)	0.008 (2)
C27	0.034 (4)	0.022 (4)	0.021 (3)	0.019 (3)	0.005 (3)	0.001 (3)
C28	0.086 (7)	0.041 (5)	0.042 (5)	0.052 (5)	0.020 (4)	0.022 (4)
N31	0.034 (3)	0.010 (3)	0.018 (3)	0.011 (2)	−0.001 (2)	−0.003 (2)
C32	0.031 (4)	0.016 (3)	0.022 (3)	0.011 (3)	0.002 (3)	0.002 (2)
Se32	0.0651 (6)	0.0163 (4)	0.0275 (4)	0.0273 (4)	−0.0039 (4)	−0.0026 (3)
N33	0.036 (3)	0.009 (2)	0.022 (3)	0.013 (2)	0.004 (2)	0.006 (2)
O34	0.045 (3)	0.012 (2)	0.020 (2)	0.015 (2)	0.000 (2)	−0.0016 (18)
C34	0.032 (4)	0.012 (3)	0.021 (3)	0.009 (3)	0.006 (3)	0.002 (2)
C35	0.039 (4)	0.005 (3)	0.023 (3)	0.012 (3)	0.006 (3)	0.000 (2)
C36	0.029 (4)	0.013 (3)	0.024 (3)	0.012 (3)	0.007 (3)	0.007 (2)
C37	0.043 (4)	0.017 (3)	0.021 (3)	0.020 (3)	0.003 (3)	0.001 (3)
C38	0.055 (5)	0.022 (4)	0.030 (4)	0.025 (3)	0.011 (3)	0.009 (3)

Geometric parameters (Å, º) top

N11—C12	1.355 (7)	C25—C26	1.347 (9)
N11—C16	1.384 (7)	C25—H25	0.9500
N11—H11	0.8800	C26—C27	1.510 (8)
C12—N13	1.351 (8)	C27—C28	1.504 (9)
C12—Se12	1.835 (6)	C27—H27A	0.9900
N13—C14	1.386 (8)	C27—H27B	0.9900
N13—H13	0.8800	C28—H28A	0.9800
C14—O14	1.240 (7)	C28—H28B	0.9800
C14—C15	1.450 (8)	C28—H28C	0.9800
C15—C16	1.353 (9)	N31—C32	1.353 (8)
C15—H15	0.9500	N31—C36	1.382 (8)
C16—C17	1.504 (8)	N31—H31	0.8800
C17—C18	1.534 (9)	C32—N33	1.349 (8)
C17—H17A	0.9900	C32—Se32	1.828 (6)
C17—H17B	0.9900	N33—C34	1.410 (8)
C18—H18A	0.9800	N33—H33	0.8800
C18—H18B	0.9800	O34—C34	1.227 (7)
C18—H18C	0.9800	C34—C35	1.431 (9)
N21—C22	1.340 (7)	C35—C36	1.347 (9)
N21—C26	1.363 (8)	C35—H35	0.9500
N21—H21	0.8800	C36—C37	1.503 (8)
Se22—C22	1.848 (6)	C37—C38	1.530 (8)
C22—N23	1.350 (8)	C37—H37A	0.9900
N23—C24	1.397 (8)	C37—H37B	0.9900
N23—H23	0.8800	C38—H38A	0.9800
C24—O24	1.241 (7)	C38—H38B	0.9800
C24—C25	1.439 (9)	C38—H38C	0.9800

C12—N11—C16	123.3 (5)	C25—C26—N21	119.3 (6)
C12—N11—H11	118.3	C25—C26—C27	125.6 (6)
C16—N11—H11	118.3	N21—C26—C27	115.1 (5)
N13—C12—N11	115.3 (5)	C28—C27—C26	115.9 (5)
N13—C12—Se12	121.6 (4)	C28—C27—H27A	108.3
N11—C12—Se12	123.2 (4)	C26—C27—H27A	108.3
C12—N13—C14	127.1 (5)	C28—C27—H27B	108.3
C12—N13—H13	116.4	C26—C27—H27B	108.3
C14—N13—H13	116.4	H27A—C27—H27B	107.4
O14—C14—N13	119.9 (5)	C27—C28—H28A	109.5
O14—C14—C15	125.9 (6)	C27—C28—H28B	109.5
N13—C14—C15	114.2 (5)	H28A—C28—H28B	109.5
C16—C15—C14	119.8 (6)	C27—C28—H28C	109.5
C16—C15—H15	120.1	H28A—C28—H28C	109.5
C14—C15—H15	120.1	H28B—C28—H28C	109.5
C15—C16—N11	120.1 (5)	C32—N31—C36	124.8 (5)
C15—C16—C17	126.2 (5)	C32—N31—H31	117.6
N11—C16—C17	113.7 (5)	C36—N31—H31	117.6
C16—C17—C18	115.4 (5)	N33—C32—N31	115.0 (5)
C16—C17—H17A	108.4	N33—C32—Se32	121.3 (5)
C18—C17—H17A	108.4	N31—C32—Se32	123.7 (5)
C16—C17—H17B	108.4	C32—N33—C34	126.3 (5)
C18—C17—H17B	108.4	C32—N33—H33	116.9
H17A—C17—H17B	107.5	C34—N33—H33	116.9
C17—C18—H18A	109.5	O34—C34—N33	119.1 (6)
C17—C18—H18B	109.5	O34—C34—C35	127.2 (6)
H18A—C18—H18B	109.5	N33—C34—C35	113.7 (5)
C17—C18—H18C	109.5	C36—C35—C34	121.9 (6)
H18A—C18—H18C	109.5	C36—C35—H35	119.0
H18B—C18—H18C	109.5	C34—C35—H35	119.0
C22—N21—C26	124.5 (5)	C35—C36—N31	118.3 (5)
C22—N21—H21	117.8	C35—C36—C37	125.7 (6)
C26—N21—H21	117.8	N31—C36—C37	116.1 (5)
N21—C22—N23	116.2 (5)	C36—C37—C38	114.5 (5)
N21—C22—Se22	121.0 (4)	C36—C37—H37A	108.6
N23—C22—Se22	122.8 (4)	C38—C37—H37A	108.6
C22—N23—C24	124.6 (5)	C36—C37—H37B	108.6
C22—N23—H23	117.7	C38—C37—H37B	108.6
C24—N23—H23	117.7	H37A—C37—H37B	107.6
O24—C24—N23	119.3 (6)	C37—C38—H38A	109.5
O24—C24—C25	125.5 (6)	C37—C38—H38B	109.5
N23—C24—C25	115.1 (5)	H38A—C38—H38B	109.5
C26—C25—C24	120.1 (6)	C37—C38—H38C	109.5
C26—C25—H25	120.0	H38A—C38—H38C	109.5
C24—C25—H25	120.0	H38B—C38—H38C	109.5

(3) top

Crystal data top

C₇H₁₀N₂OSe	D_x = 1.684 Mg m⁻³
M_r = 217.13	Synchrotron radiation, λ = 0.6775 Å
Orthorhombic, Pbca	Cell parameters from 3142 reflections
a = 10.568 (7) Å	θ = 2.6–27.5°
b = 11.257 (7) Å	µ = 4.33 mm⁻¹
c = 28.79 (2) Å	T = 120 K
V = 3425 (4) Å³	Lath, colourless
Z = 16	0.20 × 0.02 × 0.01 mm
F(000) = 1728

Data collection top

Bruker SMART APEXII CCD diffractometer	3471 independent reflections
Radiation source: Daresbury SRS station 9.8	2417 reflections with I > 2σ(I)
Silicon 111 monochromator	R_int = 0.250
fine–slice ω scans	θ_max = 25.0°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −13→13
T_min = 0.260, T_max = 1.000	k = −14→14
24855 measured reflections	l = −35→35

Refinement top

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)] = 0.173	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.408	H-atom parameters constrained
S = 1.18	w = 1/[σ²(F_o²) + (0.025P)² + 367.0] where P = (F_o² + 2F_c²)/3
3471 reflections	(Δ/σ)_max = 0.002
99 parameters	Δρ_max = 2.38 e Å⁻³
35 restraints	Δρ_min = −2.33 e Å⁻³

Crystal data top

C₇H₁₀N₂OSe	V = 3425 (4) Å³
M_r = 217.13	Z = 16
Orthorhombic, Pbca	Synchrotron radiation, λ = 0.6775 Å
a = 10.568 (7) Å	µ = 4.33 mm⁻¹
b = 11.257 (7) Å	T = 120 K
c = 28.79 (2) Å	0.20 × 0.02 × 0.01 mm

Data collection top

Bruker SMART APEXII CCD diffractometer	3471 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	2417 reflections with I > 2σ(I)
T_min = 0.260, T_max = 1.000	R_int = 0.250
24855 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.173	35 restraints
wR(F²) = 0.408	H-atom parameters constrained
S = 1.18	Δρ_max = 2.38 e Å⁻³
3471 reflections	Δρ_min = −2.33 e Å⁻³
99 parameters

Special details top

Refinement. Despite obtaining a synchrotron dataset from the Daresbury SRS, we could not overcome the limitations imposed by the poor crystal quality. As a result it was found that only the Se atoms could be refined anisotropically. Geometric restraints - similarity between the two independent molecules in the asymmetric unit and planarity of the aromatic ring - were found to be necessary.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Se1	0.0749 (2)	0.28948 (18)	0.32853 (8)	0.0333 (6)
C1	0.0909 (13)	0.3523 (15)	0.3871 (5)	0.028 (5)*
N2	0.1159 (11)	0.2874 (14)	0.4243 (5)	0.030 (4)*
H2N	0.1205	0.2098	0.4209	0.036*
C3	0.1356 (10)	0.3339 (16)	0.4688 (6)	0.029 (5)*
C4	0.1287 (11)	0.4523 (16)	0.4746 (6)	0.031 (5)*
H4	0.1418	0.4851	0.5046	0.038*
C5	0.1019 (10)	0.5304 (16)	0.4361 (6)	0.026 (4)*
O5	0.0948 (13)	0.6397 (11)	0.4387 (5)	0.035 (4)*
N6	0.0851 (11)	0.4741 (13)	0.3950 (5)	0.030 (4)*
H6N	0.0688	0.5192	0.3708	0.036*
C11	0.1625 (16)	0.2460 (17)	0.5061 (6)	0.033 (5)*
H11A	0.2134	0.1807	0.4925	0.040*
H11B	0.0812	0.2115	0.5165	0.040*
C12	0.232 (2)	0.294 (2)	0.5484 (7)	0.042 (6)*
H12A	0.3082	0.3376	0.5380	0.051*
H12B	0.1765	0.3504	0.5650	0.051*
C13	0.272 (3)	0.198 (2)	0.5815 (8)	0.049 (7)*
H13A	0.3187	0.2328	0.6075	0.074*
H13B	0.3262	0.1404	0.5653	0.074*
H13C	0.1967	0.1566	0.5934	0.074*
Se21	0.0605 (2)	0.98622 (17)	0.42671 (9)	0.0360 (7)
C21	0.0857 (14)	0.9209 (16)	0.3690 (6)	0.038 (6)*
N22	0.1047 (11)	0.9839 (14)	0.3309 (5)	0.032 (4)*
H22N	0.1075	1.0617	0.3337	0.038*
C23	0.1207 (11)	0.9360 (16)	0.2866 (6)	0.033 (5)*
C24	0.1164 (12)	0.8173 (16)	0.2817 (6)	0.033 (5)*
H24	0.1262	0.7833	0.2517	0.040*
C25	0.0971 (11)	0.7407 (18)	0.3212 (7)	0.073 (10)*
O25	0.0912 (12)	0.6312 (11)	0.3195 (4)	0.027 (3)*
N26	0.0822 (11)	0.7987 (14)	0.3624 (5)	0.034 (4)*
H26N	0.0691	0.7545	0.3871	0.041*
C31	0.1410 (18)	1.0226 (18)	0.2482 (7)	0.043 (6)*
H31A	0.1761	1.0967	0.2615	0.051*
H31B	0.0580	1.0421	0.2342	0.051*
C32	0.229 (2)	0.979 (2)	0.2099 (7)	0.045 (6)*
H32A	0.3116	0.9574	0.2237	0.054*
H32B	0.1927	0.9074	0.1955	0.054*
C33	0.251 (2)	1.071 (2)	0.1729 (7)	0.040 (6)*
H33A	0.3081	1.0394	0.1493	0.060*
H33B	0.2882	1.1425	0.1868	0.060*
H33C	0.1697	1.0920	0.1584	0.060*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Se1	0.0392 (13)	0.0120 (10)	0.0486 (14)	−0.0005 (10)	−0.0017 (11)	0.0015 (9)
Se21	0.0482 (14)	0.0083 (10)	0.0516 (14)	−0.0012 (10)	0.0005 (12)	0.0001 (9)

Geometric parameters (Å, º) top

Se1—C1	1.837 (16)	Se21—C21	1.835 (16)
C1—N2	1.32 (2)	C21—N22	1.32 (2)
C1—N6	1.39 (2)	C21—N26	1.39 (2)
N2—C3	1.40 (2)	N22—C23	1.40 (2)
N2—H2N	0.8800	N22—H22N	0.8800
C3—C4	1.34 (2)	C23—C24	1.34 (2)
C3—C11	1.49 (2)	C23—C31	1.49 (2)
C4—C5	1.44 (2)	C24—C25	1.44 (2)
C4—H4	0.9500	C24—H24	0.9500
C5—O5	1.23 (2)	C25—O25	1.24 (2)
C5—N6	1.36 (2)	C25—N26	1.36 (2)
N6—H6N	0.8800	N26—H26N	0.8800
C11—C12	1.52 (2)	C31—C32	1.52 (2)
C11—H11A	0.9900	C31—H31A	0.9900
C11—H11B	0.9900	C31—H31B	0.9900
C12—C13	1.50 (3)	C32—C33	1.50 (2)
C12—H12A	0.9900	C32—H32A	0.9900
C12—H12B	0.9900	C32—H32B	0.9900
C13—H13A	0.9800	C33—H33A	0.9800
C13—H13B	0.9800	C33—H33B	0.9800
C13—H13C	0.9800	C33—H33C	0.9800

N2—C1—N6	115.0 (15)	N22—C21—N26	114.9 (15)
N2—C1—Se1	123.3 (13)	N22—C21—Se21	123.9 (13)
N6—C1—Se1	121.7 (12)	N26—C21—Se21	121.2 (12)
C1—N2—C3	124.3 (15)	C21—N22—C23	124.8 (15)
C1—N2—H2N	117.9	C21—N22—H22N	117.6
C3—N2—H2N	117.9	C23—N22—H22N	117.6
C4—C3—N2	118.5 (16)	C24—C23—N22	118.4 (16)
C4—C3—C11	125.4 (16)	C24—C23—C31	125.3 (17)
N2—C3—C11	116.1 (15)	N22—C23—C31	116.3 (15)
C3—C4—C5	121.2 (17)	C23—C24—C25	121.1 (17)
C3—C4—H4	119.4	C23—C24—H24	119.4
C5—C4—H4	119.4	C25—C24—H24	119.4
O5—C5—N6	120.6 (17)	O25—C25—N26	120.4 (18)
O5—C5—C4	125.0 (17)	O25—C25—C24	125.0 (18)
N6—C5—C4	114.3 (16)	N26—C25—C24	114.6 (17)
C5—N6—C1	126.7 (15)	C25—N26—C21	126.2 (16)
C5—N6—H6N	116.7	C25—N26—H26N	116.9
C1—N6—H6N	116.7	C21—N26—H26N	116.9
C3—C11—C12	115.9 (15)	C23—C31—C32	114.7 (15)
C3—C11—H11A	108.3	C23—C31—H31A	108.6
C12—C11—H11A	108.3	C32—C31—H31A	108.6
C3—C11—H11B	108.3	C23—C31—H31B	108.6
C12—C11—H11B	108.3	C32—C31—H31B	108.6
H11A—C11—H11B	107.4	H31A—C31—H31B	107.6
C13—C12—C11	113.0 (17)	C33—C32—C31	112.8 (17)
C13—C12—H12A	109.0	C33—C32—H32A	109.0
C11—C12—H12A	109.0	C31—C32—H32A	109.0
C13—C12—H12B	109.0	C33—C32—H32B	109.0
C11—C12—H12B	109.0	C31—C32—H32B	109.0
H12A—C12—H12B	107.8	H32A—C32—H32B	107.8
C12—C13—H13A	109.5	C32—C33—H33A	109.5
C12—C13—H13B	109.5	C32—C33—H33B	109.5
H13A—C13—H13B	109.5	H33A—C33—H33B	109.5
C12—C13—H13C	109.5	C32—C33—H33C	109.5
H13A—C13—H13C	109.5	H33A—C33—H33C	109.5
H13B—C13—H13C	109.5	H33B—C33—H33C	109.5

(4) top

Crystal data top

C₇H₁₀N₂OSe	Z = 6
M_r = 217.13	F(000) = 648
Triclinic, P1	D_x = 1.650 Mg m⁻³
a = 8.9192 (9) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.6403 (10) Å	Cell parameters from 3689 reflections
c = 15.1965 (15) Å	θ = 2.4–27.6°
α = 106.019 (2)°	µ = 4.24 mm⁻¹
β = 105.366 (2)°	T = 150 K
γ = 96.166 (2)°	Tablet, colourless
V = 1311.0 (2) Å³	0.25 × 0.14 × 0.06 mm

Data collection top

Bruker SMART APEX CCD area detector diffractometer	5780 independent reflections
Radiation source: sealed tube	4932 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.013
ω scans	θ_max = 27.6°, θ_min = 2.4°
Absorption correction: multi-scan Bruker SADABS v2.03	h = −11→7
T_min = 0.581, T_max = 0.770	k = −13→13
8163 measured reflections	l = −17→19

Refinement top

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)] = 0.028	Hydrogen site location: geometrically placed, NH from delta-F and then idealised
wR(F²) = 0.071	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.033P)² + 0.854P] where P = (F_o² + 2F_c²)/3
5780 reflections	(Δ/σ)_max = 0.001
298 parameters	Δρ_max = 0.65 e Å⁻³
0 restraints	Δρ_min = −0.40 e Å⁻³

Crystal data top

C₇H₁₀N₂OSe	γ = 96.166 (2)°
M_r = 217.13	V = 1311.0 (2) Å³
Triclinic, P1	Z = 6
a = 8.9192 (9) Å	Mo Kα radiation
b = 10.6403 (10) Å	µ = 4.24 mm⁻¹
c = 15.1965 (15) Å	T = 150 K
α = 106.019 (2)°	0.25 × 0.14 × 0.06 mm
β = 105.366 (2)°

Data collection top

Bruker SMART APEX CCD area detector diffractometer	5780 independent reflections
Absorption correction: multi-scan Bruker SADABS v2.03	4932 reflections with I > 2σ(I)
T_min = 0.581, T_max = 0.770	R_int = 0.013
8163 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	0 restraints
wR(F²) = 0.071	H-atom parameters constrained
S = 1.04	Δρ_max = 0.65 e Å⁻³
5780 reflections	Δρ_min = −0.40 e Å⁻³
298 parameters

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Se1	1.07398 (3)	0.80241 (2)	0.489662 (16)	0.02136 (7)
O1	0.9476 (2)	0.59638 (17)	0.12915 (12)	0.0285 (4)
N1	0.9208 (2)	0.89862 (18)	0.34418 (13)	0.0183 (4)
H1A	0.9156	0.9646	0.3925	0.022*
C2	0.9924 (3)	0.8001 (2)	0.36425 (16)	0.0176 (4)
N3	0.9998 (2)	0.70197 (19)	0.28899 (14)	0.0196 (4)
H3A	1.0503	0.6392	0.3014	0.024*
C4	0.9335 (3)	0.6915 (2)	0.19217 (17)	0.0219 (5)
C5	0.8561 (3)	0.7987 (2)	0.17681 (17)	0.0226 (5)
H5A	0.8050	0.7969	0.1130	0.027*
C6	0.8549 (3)	0.9013 (2)	0.25115 (17)	0.0193 (5)
C7	0.7970 (3)	1.0269 (2)	0.24404 (17)	0.0218 (5)
H7A	0.7532	1.0597	0.2985	0.026*
C8	0.6658 (3)	1.0049 (3)	0.15028 (19)	0.0305 (6)
H8A	0.5767	0.9373	0.1444	0.046*
H8B	0.7066	0.9745	0.0958	0.046*
H8C	0.6298	1.0888	0.1504	0.046*
C9	0.9385 (3)	1.1326 (2)	0.2569 (2)	0.0304 (6)
H9A	1.0200	1.1450	0.3180	0.046*
H9B	0.9038	1.2170	0.2574	0.046*
H9C	0.9824	1.1034	0.2036	0.046*
Se1A	0.69491 (3)	0.71890 (3)	−0.093473 (18)	0.03059 (8)
O1A	0.4581 (3)	0.25574 (19)	−0.32509 (13)	0.0393 (5)
N1A	0.7470 (2)	0.4752 (2)	−0.06506 (14)	0.0236 (4)
H1AA	0.8105	0.5243	−0.0079	0.028*
C2A	0.6681 (3)	0.5381 (2)	−0.12369 (17)	0.0238 (5)
N3A	0.5675 (3)	0.4566 (2)	−0.20863 (15)	0.0264 (5)
H3AA	0.5075	0.4945	−0.2454	0.032*
C4A	0.5493 (3)	0.3187 (3)	−0.24379 (19)	0.0294 (6)
C5A	0.6407 (3)	0.2611 (3)	−0.17789 (19)	0.0288 (6)
H5AA	0.6356	0.1675	−0.1966	0.035*
C6A	0.7335 (3)	0.3383 (2)	−0.08979 (18)	0.0244 (5)
C7A	0.8227 (3)	0.2883 (3)	−0.01137 (18)	0.0282 (6)
H7AA	0.9309	0.3458	0.0194	0.034*
C8A	0.7373 (4)	0.3039 (3)	0.0660 (2)	0.0383 (7)
H8AA	0.7949	0.2717	0.1172	0.057*
H8AB	0.6290	0.2517	0.0367	0.057*
H8AC	0.7339	0.3981	0.0931	0.057*
C9A	0.8418 (4)	0.1441 (3)	−0.0491 (2)	0.0366 (7)
H9AA	0.8965	0.1363	−0.0979	0.055*
H9AB	0.7371	0.0855	−0.0778	0.055*
H9AC	0.9042	0.1181	0.0042	0.055*
Se1B	0.75370 (3)	0.45066 (2)	0.338610 (18)	0.02597 (7)
N1B	0.6585 (2)	0.63716 (19)	0.47242 (14)	0.0200 (4)
H1BA	0.6238	0.6691	0.4248	0.024*
O1B	0.8146 (3)	0.48679 (19)	0.68468 (14)	0.0357 (5)
C2B	0.7292 (3)	0.5317 (2)	0.45594 (17)	0.0201 (5)
N3B	0.7807 (2)	0.4863 (2)	0.53135 (14)	0.0228 (4)
H3BA	0.8293	0.4183	0.5221	0.027*
C4B	0.7638 (3)	0.5376 (2)	0.62238 (18)	0.0243 (5)
C5B	0.6852 (3)	0.6498 (2)	0.63353 (18)	0.0225 (5)
H5BA	0.6675	0.6895	0.6931	0.027*
C6B	0.6366 (3)	0.6989 (2)	0.56018 (17)	0.0186 (5)
C7B	0.5636 (3)	0.8212 (2)	0.56518 (18)	0.0218 (5)
H7BA	0.4642	0.7970	0.5096	0.026*
C8B	0.6764 (3)	0.9317 (2)	0.5549 (2)	0.0292 (6)
H8BA	0.6281	1.0106	0.5581	0.044*
H8BB	0.6966	0.9005	0.4929	0.044*
H8BC	0.7766	0.9546	0.6073	0.044*
C9B	0.5202 (4)	0.8717 (3)	0.6568 (2)	0.0343 (6)
H9BA	0.4477	0.8005	0.6625	0.051*
H9BB	0.4684	0.9480	0.6549	0.051*
H9BC	0.6165	0.8993	0.7123	0.051*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Se1	0.03137 (14)	0.01777 (11)	0.01345 (11)	0.00925 (9)	0.00318 (9)	0.00452 (9)
O1	0.0422 (11)	0.0256 (9)	0.0151 (8)	0.0135 (8)	0.0060 (7)	0.0025 (7)
N1	0.0231 (10)	0.0168 (9)	0.0145 (9)	0.0078 (8)	0.0050 (8)	0.0035 (7)
C2	0.0208 (11)	0.0162 (10)	0.0140 (10)	0.0028 (9)	0.0038 (9)	0.0037 (8)
N3	0.0263 (11)	0.0169 (9)	0.0164 (9)	0.0083 (8)	0.0051 (8)	0.0063 (8)
C4	0.0256 (12)	0.0211 (11)	0.0166 (11)	0.0024 (10)	0.0047 (9)	0.0049 (9)
C5	0.0269 (13)	0.0246 (11)	0.0164 (11)	0.0084 (10)	0.0031 (9)	0.0088 (9)
C6	0.0177 (11)	0.0228 (11)	0.0181 (11)	0.0052 (9)	0.0033 (9)	0.0093 (9)
C7	0.0255 (12)	0.0240 (11)	0.0184 (12)	0.0107 (10)	0.0067 (10)	0.0085 (9)
C8	0.0265 (13)	0.0338 (14)	0.0315 (15)	0.0098 (11)	0.0013 (11)	0.0166 (12)
C9	0.0331 (14)	0.0229 (12)	0.0322 (14)	0.0063 (11)	0.0021 (11)	0.0115 (11)
Se1A	0.04401 (17)	0.02449 (13)	0.01969 (13)	0.01027 (11)	0.00385 (11)	0.00577 (10)
O1A	0.0535 (13)	0.0277 (10)	0.0237 (10)	0.0024 (9)	−0.0071 (9)	0.0079 (8)
N1A	0.0264 (11)	0.0260 (10)	0.0146 (10)	0.0054 (9)	0.0017 (8)	0.0046 (8)
C2A	0.0270 (13)	0.0258 (12)	0.0201 (12)	0.0072 (10)	0.0089 (10)	0.0073 (10)
N3A	0.0338 (12)	0.0248 (10)	0.0176 (10)	0.0071 (9)	0.0011 (9)	0.0080 (8)
C4A	0.0379 (15)	0.0269 (13)	0.0231 (13)	0.0050 (11)	0.0060 (11)	0.0113 (11)
C5A	0.0360 (15)	0.0224 (12)	0.0253 (13)	0.0052 (11)	0.0040 (11)	0.0087 (10)
C6A	0.0266 (13)	0.0279 (12)	0.0211 (12)	0.0068 (10)	0.0076 (10)	0.0107 (10)
C7A	0.0301 (14)	0.0312 (13)	0.0224 (13)	0.0059 (11)	0.0024 (10)	0.0129 (11)
C8A	0.0487 (18)	0.0440 (17)	0.0297 (15)	0.0100 (14)	0.0134 (13)	0.0216 (13)
C9A	0.0392 (16)	0.0345 (15)	0.0380 (16)	0.0135 (13)	0.0064 (13)	0.0175 (13)
Se1B	0.03340 (15)	0.02453 (13)	0.01974 (13)	0.00943 (10)	0.00871 (10)	0.00476 (10)
N1B	0.0211 (10)	0.0196 (9)	0.0193 (10)	0.0048 (8)	0.0049 (8)	0.0074 (8)
O1B	0.0572 (13)	0.0372 (10)	0.0286 (10)	0.0305 (10)	0.0214 (9)	0.0194 (9)
C2B	0.0203 (12)	0.0181 (10)	0.0217 (12)	0.0035 (9)	0.0063 (9)	0.0064 (9)
N3B	0.0294 (11)	0.0209 (10)	0.0228 (10)	0.0139 (9)	0.0105 (9)	0.0087 (8)
C4B	0.0295 (13)	0.0236 (12)	0.0245 (13)	0.0101 (10)	0.0105 (10)	0.0110 (10)
C5B	0.0270 (13)	0.0209 (11)	0.0229 (12)	0.0094 (10)	0.0104 (10)	0.0078 (10)
C6B	0.0164 (11)	0.0159 (10)	0.0241 (12)	0.0038 (9)	0.0070 (9)	0.0061 (9)
C7B	0.0200 (12)	0.0170 (10)	0.0278 (13)	0.0067 (9)	0.0049 (10)	0.0072 (9)
C8B	0.0283 (14)	0.0208 (12)	0.0409 (16)	0.0061 (10)	0.0102 (12)	0.0135 (11)
C9B	0.0436 (17)	0.0268 (13)	0.0432 (17)	0.0174 (12)	0.0256 (14)	0.0122 (12)

Geometric parameters (Å, º) top

Se1—C2	1.843 (2)	C7B—C8B	1.533 (3)
O1—C4	1.230 (3)	N1—H1A	0.88
N1—C2	1.348 (3)	N3—H3A	0.88
N1—C6	1.389 (3)	N1A—H1AA	0.88
C2—N3	1.341 (3)	N3A—H3AA	0.88
N3—C4	1.400 (3)	N1B—H1BA	0.88
C4—C5	1.437 (3)	N3B—H3BA	0.88
C5—C6	1.340 (3)	C5—H5A	0.95
C6—C7	1.504 (3)	C7—H7A	1.00
C7—C8	1.526 (3)	C8—H8C	0.98
C7—C9	1.529 (4)	C8—H8B	0.98
Se1A—C2A	1.824 (2)	C8—H8A	0.98
O1A—C4A	1.237 (3)	C9—H9C	0.98
N1A—C2A	1.354 (3)	C9—H9A	0.98
N1A—C6A	1.383 (3)	C9—H9B	0.98
C2A—N3A	1.351 (3)	C5A—H5AA	0.95
N3A—C4A	1.391 (3)	C7A—H7AA	1.00
C4A—C5A	1.434 (3)	C8A—H8AB	0.98
C5A—C6A	1.346 (3)	C8A—H8AC	0.98
C6A—C7A	1.508 (3)	C8A—H8AA	0.98
C7A—C9A	1.528 (4)	C9A—H9AC	0.98
C7A—C8A	1.543 (4)	C9A—H9AA	0.98
Se1B—C2B	1.835 (2)	C9A—H9AB	0.98
N1B—C2B	1.342 (3)	C5B—H5BA	0.95
N1B—C6B	1.389 (3)	C7B—H7BA	1.00
O1B—C4B	1.226 (3)	C8B—H8BA	0.98
C2B—N3B	1.353 (3)	C8B—H8BB	0.98
N3B—C4B	1.395 (3)	C8B—H8BC	0.98
C4B—C5B	1.441 (3)	C9B—H9BA	0.98
C5B—C6B	1.348 (3)	C9B—H9BB	0.98
C6B—C7B	1.509 (3)	C9B—H9BC	0.98
C7B—C9B	1.515 (4)

C2—N1—C6	123.3 (2)	C6B—N1B—H1BA	118
N3—C2—N1	116.7 (2)	C4B—N3B—H3BA	117
N3—C2—Se1	122.59 (17)	C2B—N3B—H3BA	117
N1—C2—Se1	120.70 (17)	C4—C5—H5A	120
C2—N3—C4	125.2 (2)	C6—C5—H5A	119
O1—C4—N3	119.3 (2)	C9—C7—H7A	108
O1—C4—C5	126.0 (2)	C6—C7—H7A	108
N3—C4—C5	114.6 (2)	C8—C7—H7A	108
C6—C5—C4	121.0 (2)	H8B—C8—H8C	109
C5—C6—N1	119.0 (2)	C7—C8—H8A	109
C5—C6—C7	125.6 (2)	H8A—C8—H8C	109
N1—C6—C7	115.3 (2)	C7—C8—H8C	109
C6—C7—C8	112.8 (2)	H8A—C8—H8B	109
C6—C7—C9	108.6 (2)	C7—C8—H8B	109
C8—C7—C9	111.5 (2)	H9A—C9—H9B	110
C2A—N1A—C6A	123.9 (2)	C7—C9—H9C	109
N3A—C2A—N1A	115.0 (2)	H9B—C9—H9C	109
N3A—C2A—Se1A	121.33 (18)	C7—C9—H9B	109
N1A—C2A—Se1A	123.65 (18)	H9A—C9—H9C	109
C2A—N3A—C4A	126.5 (2)	C7—C9—H9A	109
O1A—C4A—N3A	120.3 (2)	C4A—C5A—H5AA	120
O1A—C4A—C5A	125.3 (2)	C6A—C5A—H5AA	120
N3A—C4A—C5A	114.4 (2)	C9A—C7A—H7AA	108
C6A—C5A—C4A	120.7 (2)	C8A—C7A—H7AA	108
C5A—C6A—N1A	119.3 (2)	C6A—C7A—H7AA	108
C5A—C6A—C7A	125.4 (2)	H8AA—C8A—H8AB	109
N1A—C6A—C7A	115.2 (2)	C7A—C8A—H8AB	109
C6A—C7A—C9A	112.9 (2)	C7A—C8A—H8AC	109
C6A—C7A—C8A	109.1 (2)	H8AB—C8A—H8AC	109
C9A—C7A—C8A	110.6 (2)	H8AA—C8A—H8AC	110
C2B—N1B—C6B	123.9 (2)	C7A—C8A—H8AA	109
N1B—C2B—N3B	115.9 (2)	H9AA—C9A—H9AB	110
N1B—C2B—Se1B	122.91 (17)	H9AA—C9A—H9AC	109
N3B—C2B—Se1B	121.19 (17)	H9AB—C9A—H9AC	109
C2B—N3B—C4B	125.9 (2)	C7A—C9A—H9AC	109
O1B—C4B—N3B	119.7 (2)	C7A—C9A—H9AA	109
O1B—C4B—C5B	125.8 (2)	C7A—C9A—H9AB	109
N3B—C4B—C5B	114.5 (2)	C4B—C5B—H5BA	120
C6B—C5B—C4B	120.6 (2)	C6B—C5B—H5BA	120
C5B—C6B—N1B	119.2 (2)	C6B—C7B—H7BA	108
C5B—C6B—C7B	125.5 (2)	C8B—C7B—H7BA	108
N1B—C6B—C7B	115.4 (2)	C9B—C7B—H7BA	108
C6B—C7B—C9B	112.8 (2)	C7B—C8B—H8BA	109
C6B—C7B—C8B	110.0 (2)	C7B—C8B—H8BB	109
C9B—C7B—C8B	110.1 (2)	C7B—C8B—H8BC	109
C6—N1—H1A	118	H8BA—C8B—H8BB	110
C2—N1—H1A	118	H8BA—C8B—H8BC	109
C4—N3—H3A	117	H8BB—C8B—H8BC	110
C2—N3—H3A	117	C7B—C9B—H9BA	109
C6A—N1A—H1AA	118	C7B—C9B—H9BB	109
C2A—N1A—H1AA	118	C7B—C9B—H9BC	109
C2A—N3A—H3AA	117	H9BA—C9B—H9BB	109
C4A—N3A—H3AA	117	H9BA—C9B—H9BC	109
C2B—N1B—H1BA	118	H9BB—C9B—H9BC	109

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O1Bⁱ	0.88	1.91	2.782 (3)	169
N1A—H1AA···O1	0.88	2.00	2.860 (3)	167
N1B—H1BA···O1Aⁱⁱ	0.88	1.92	2.796 (3)	177
N1—H1A···Se1ⁱⁱⁱ	0.88	2.60	3.460 (2)	165
N3B—H3BA···Se1ⁱ	0.88	2.56	3.428 (2)	167
N3A—H3AA···Se1Bⁱⁱ	0.88	2.60	3.430 (2)	157

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

(4.CH2Cl2) top

Crystal data top

C₈H₁₂Cl₂N₂OSe	Z = 4
M_r = 302.06	F(000) = 600
Triclinic, P1	D_x = 1.685 Mg m⁻³
a = 8.841 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.259 (3) Å	Cell parameters from 2249 reflections
c = 12.424 (4) Å	θ = 2.4–24.6°
α = 90.450 (5)°	µ = 3.57 mm⁻¹
β = 105.350 (4)°	T = 150 K
γ = 92.945 (5)°	Plate, colourless
V = 1190.7 (6) Å³	0.36 × 0.22 × 0.02 mm

Data collection top

Bruker SMART APEX CCD area detector diffractometer	6193 independent reflections
Radiation source: sealed tube	4391 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.050
ω scans	θ_max = 27.5°, θ_min = 2.4°
Absorption correction: multi-scan (TWINABS version 1.02; Bruker, 2001)	h = −11→11
T_min = 0.684, T_max = 1.000	k = −14→14
10743 measured reflections	l = −16→16

Refinement top

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.099	H-atom parameters constrained
S = 0.97	w = 1/[σ²(F_o²) + (0.0305P)²] where P = (F_o² + 2F_c²)/3
6193 reflections	(Δ/σ)_max = 0.001
254 parameters	Δρ_max = 0.87 e Å⁻³
0 restraints	Δρ_min = −0.51 e Å⁻³

Crystal data top

C₈H₁₂Cl₂N₂OSe	γ = 92.945 (5)°
M_r = 302.06	V = 1190.7 (6) Å³
Triclinic, P1	Z = 4
a = 8.841 (3) Å	Mo Kα radiation
b = 11.259 (3) Å	µ = 3.57 mm⁻¹
c = 12.424 (4) Å	T = 150 K
α = 90.450 (5)°	0.36 × 0.22 × 0.02 mm
β = 105.350 (4)°

Data collection top

Bruker SMART APEX CCD area detector diffractometer	6193 independent reflections
Absorption correction: multi-scan (TWINABS version 1.02; Bruker, 2001)	4391 reflections with I > 2σ(I)
T_min = 0.684, T_max = 1.000	R_int = 0.050
10743 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.099	H-atom parameters constrained
S = 0.97	Δρ_max = 0.87 e Å⁻³
6193 reflections	Δρ_min = −0.51 e Å⁻³
254 parameters

Special details top

Refinement. The crystal was found to be merohedrally twinned by 180 degree rotation about [001]. Data reduction employed two orientation matrices and the minor twin component refined to approximately 0.2.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
N1	0.9470 (5)	0.4519 (4)	0.1485 (4)	0.0199 (11)
H1	0.9432	0.3739	0.1409	0.024*
C2	0.8502 (6)	0.5128 (5)	0.0686 (5)	0.0193 (13)
Se2	0.70612 (7)	0.44056 (5)	−0.05032 (5)	0.02365 (16)
N3	0.8650 (5)	0.6324 (4)	0.0822 (4)	0.0211 (11)
H3	0.8029	0.6740	0.0308	0.025*
C4	0.9684 (6)	0.6954 (5)	0.1692 (5)	0.0209 (13)
O4	0.9745 (4)	0.8050 (3)	0.1704 (3)	0.0289 (10)
C5	1.0622 (6)	0.6232 (5)	0.2538 (4)	0.0186 (13)
H5	1.1316	0.6601	0.3185	0.022*
C6	1.0522 (6)	0.5038 (5)	0.2419 (4)	0.0175 (13)
C7	1.1449 (6)	0.4176 (5)	0.3218 (4)	0.0187 (13)
H7	1.1803	0.3554	0.2776	0.022*
C8	1.2905 (6)	0.4788 (5)	0.4025 (5)	0.0309 (15)
H8A	1.3569	0.5178	0.3598	0.046*
H8B	1.3500	0.4194	0.4509	0.046*
H8C	1.2577	0.5384	0.4484	0.046*
C9	1.0398 (7)	0.3559 (5)	0.3887 (5)	0.0315 (16)
H9A	0.9469	0.3170	0.3369	0.047*
H9B	1.0068	0.4154	0.4346	0.047*
H9C	1.0990	0.2964	0.4370	0.047*
N11	0.6861 (5)	1.1339 (4)	−0.0501 (4)	0.0180 (11)
H11	0.6930	1.2121	−0.0462	0.022*
C12	0.7948 (6)	1.0748 (5)	0.0249 (4)	0.0208 (13)
Se12	0.95588 (7)	1.14876 (5)	0.13130 (5)	0.02879 (18)
N13	0.7749 (5)	0.9551 (4)	0.0180 (3)	0.0216 (11)
H13	0.8434	0.9145	0.0660	0.026*
C14	0.6542 (6)	0.8899 (5)	−0.0593 (5)	0.0238 (14)
O14	0.6489 (4)	0.7804 (3)	−0.0561 (3)	0.0331 (11)
C15	0.5490 (6)	0.9598 (5)	−0.1357 (5)	0.0241 (14)
H15	0.4645	0.9217	−0.1908	0.029*
C16	0.5666 (6)	1.0800 (5)	−0.1315 (4)	0.0159 (12)
C17	0.4665 (6)	1.1617 (5)	−0.2126 (4)	0.0187 (13)
H17	0.4393	1.2285	−0.1688	0.022*
C18	0.3155 (6)	1.1015 (5)	−0.2820 (5)	0.0312 (15)
H18A	0.2548	1.0683	−0.2327	0.047*
H18B	0.3395	1.0375	−0.3277	0.047*
H18C	0.2541	1.1598	−0.3308	0.047*
C19	0.5621 (7)	1.2137 (5)	−0.2871 (5)	0.0302 (15)
H19A	0.6598	1.2525	−0.2410	0.045*
H19B	0.5014	1.2723	−0.3359	0.045*
H19C	0.5869	1.1500	−0.3328	0.045*
C20	0.4146 (7)	0.6182 (5)	−0.2314 (5)	0.0339 (16)
H20A	0.3578	0.6505	−0.1798	0.041*
H20B	0.5261	0.6128	−0.1895	0.041*
Cl1	0.33267 (17)	0.47388 (12)	−0.27928 (13)	0.0310 (4)
Cl2	0.40267 (19)	0.71468 (13)	−0.34259 (14)	0.0392 (4)
C21	0.1276 (6)	−0.0082 (5)	0.3734 (5)	0.0302 (15)
H21A	0.1037	−0.0451	0.2977	0.036*
H21B	0.0372	0.0382	0.3776	0.036*
Cl3	0.29574 (19)	0.08815 (14)	0.39413 (15)	0.0431 (5)
Cl4	0.1519 (2)	−0.12112 (13)	0.47302 (13)	0.0420 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.024 (3)	0.005 (2)	0.027 (3)	−0.0004 (19)	0.001 (2)	−0.003 (2)
C2	0.019 (3)	0.017 (3)	0.019 (3)	−0.001 (2)	0.001 (3)	0.002 (2)
Se2	0.0299 (4)	0.0141 (3)	0.0214 (3)	−0.0004 (3)	−0.0027 (3)	−0.0021 (3)
N3	0.022 (3)	0.012 (2)	0.024 (3)	0.003 (2)	−0.005 (2)	0.004 (2)
C4	0.026 (3)	0.018 (3)	0.018 (3)	0.001 (3)	0.004 (3)	−0.004 (3)
O4	0.040 (3)	0.010 (2)	0.027 (2)	0.0014 (18)	−0.007 (2)	−0.0035 (18)
C5	0.018 (3)	0.022 (3)	0.012 (3)	0.000 (2)	−0.002 (2)	−0.003 (2)
C6	0.016 (3)	0.022 (3)	0.017 (3)	0.001 (2)	0.008 (3)	−0.004 (2)
C7	0.016 (3)	0.019 (3)	0.021 (3)	0.003 (2)	0.005 (3)	0.003 (2)
C8	0.029 (4)	0.028 (4)	0.033 (4)	0.006 (3)	0.001 (3)	0.005 (3)
C9	0.045 (4)	0.016 (3)	0.031 (4)	0.004 (3)	0.005 (3)	0.009 (3)
N11	0.024 (3)	0.006 (2)	0.021 (3)	−0.0002 (19)	0.001 (2)	−0.001 (2)
C12	0.028 (3)	0.015 (3)	0.020 (3)	0.001 (2)	0.008 (3)	−0.002 (2)
Se12	0.0347 (4)	0.0138 (3)	0.0279 (4)	−0.0002 (3)	−0.0089 (3)	−0.0023 (3)
N13	0.026 (3)	0.014 (3)	0.017 (3)	0.003 (2)	−0.007 (2)	−0.002 (2)
C14	0.021 (3)	0.024 (3)	0.025 (4)	0.003 (3)	0.004 (3)	−0.003 (3)
O14	0.035 (3)	0.013 (2)	0.041 (3)	−0.0010 (18)	−0.008 (2)	0.001 (2)
C15	0.024 (3)	0.022 (3)	0.023 (3)	−0.003 (3)	0.002 (3)	−0.001 (3)
C16	0.011 (3)	0.022 (3)	0.016 (3)	0.002 (2)	0.007 (2)	0.001 (3)
C17	0.023 (3)	0.018 (3)	0.014 (3)	0.003 (2)	0.004 (3)	−0.001 (2)
C18	0.032 (4)	0.032 (4)	0.026 (4)	0.004 (3)	−0.001 (3)	0.005 (3)
C19	0.043 (4)	0.021 (3)	0.023 (4)	0.002 (3)	0.003 (3)	0.004 (3)
C20	0.043 (4)	0.018 (3)	0.035 (4)	−0.002 (3)	0.002 (3)	0.005 (3)
Cl1	0.0353 (9)	0.0190 (8)	0.0384 (10)	−0.0031 (6)	0.0103 (8)	−0.0032 (7)
Cl2	0.0533 (11)	0.0247 (9)	0.0368 (10)	−0.0058 (7)	0.0085 (8)	0.0053 (7)
C21	0.037 (4)	0.023 (3)	0.024 (4)	−0.008 (3)	−0.001 (3)	0.005 (3)
Cl3	0.0420 (10)	0.0348 (10)	0.0516 (12)	−0.0095 (8)	0.0132 (9)	−0.0035 (8)
Cl4	0.0661 (12)	0.0278 (9)	0.0300 (10)	0.0019 (8)	0.0089 (9)	0.0053 (7)

Geometric parameters (Å, º) top

N1—C2	1.346 (6)	C12—Se12	1.825 (5)
N1—C6	1.383 (6)	N13—C14	1.402 (6)
N1—H1	0.8800	N13—H13	0.8800
C2—N3	1.351 (6)	C14—O14	1.233 (6)
C2—Se2	1.829 (5)	C14—C15	1.416 (7)
N3—C4	1.381 (6)	C15—C16	1.354 (7)
N3—H3	0.8800	C15—H15	0.9500
C4—O4	1.232 (6)	C16—C17	1.506 (7)
C4—C5	1.440 (7)	C17—C18	1.508 (7)
C5—C6	1.348 (7)	C17—C19	1.512 (7)
C5—H5	0.9500	C17—H17	1.0000
C6—C7	1.505 (7)	C18—H18A	0.9800
C7—C8	1.534 (7)	C18—H18B	0.9800
C7—C9	1.545 (7)	C18—H18C	0.9800
C7—H7	1.0000	C19—H19A	0.9800
C8—H8A	0.9800	C19—H19B	0.9800
C8—H8B	0.9800	C19—H19C	0.9800
C8—H8C	0.9800	C20—Cl2	1.749 (6)
C9—H9A	0.9800	C20—Cl1	1.776 (5)
C9—H9B	0.9800	C20—H20A	0.9900
C9—H9C	0.9800	C20—H20B	0.9900
N11—C12	1.355 (6)	C21—Cl3	1.755 (5)
N11—C16	1.366 (6)	C21—Cl4	1.763 (5)
N11—H11	0.8800	C21—H21A	0.9900
C12—N13	1.350 (6)	C21—H21B	0.9900

C2—N1—C6	124.3 (4)	C12—N13—C14	125.6 (5)
C2—N1—H1	117.8	C12—N13—H13	117.2
C6—N1—H1	117.8	C14—N13—H13	117.2
N1—C2—N3	115.4 (5)	O14—C14—N13	119.0 (5)
N1—C2—Se2	123.0 (4)	O14—C14—C15	126.3 (5)
N3—C2—Se2	121.6 (4)	N13—C14—C15	114.7 (5)
C2—N3—C4	126.1 (5)	C16—C15—C14	121.2 (5)
C2—N3—H3	116.9	C16—C15—H15	119.4
C4—N3—H3	116.9	C14—C15—H15	119.4
O4—C4—N3	120.0 (5)	C15—C16—N11	118.8 (5)
O4—C4—C5	125.1 (5)	C15—C16—C17	125.1 (5)
N3—C4—C5	114.8 (5)	N11—C16—C17	116.0 (4)
C6—C5—C4	120.5 (5)	C16—C17—C18	113.4 (4)
C6—C5—H5	119.7	C16—C17—C19	108.7 (4)
C4—C5—H5	119.7	C18—C17—C19	110.3 (5)
C5—C6—N1	118.7 (5)	C16—C17—H17	108.1
C5—C6—C7	126.3 (5)	C18—C17—H17	108.1
N1—C6—C7	114.9 (4)	C19—C17—H17	108.1
C6—C7—C8	112.0 (4)	C17—C18—H18A	109.5
C6—C7—C9	110.0 (4)	C17—C18—H18B	109.5
C8—C7—C9	109.7 (5)	H18A—C18—H18B	109.5
C6—C7—H7	108.4	C17—C18—H18C	109.5
C8—C7—H7	108.4	H18A—C18—H18C	109.5
C9—C7—H7	108.4	H18B—C18—H18C	109.5
C7—C8—H8A	109.5	C17—C19—H19A	109.5
C7—C8—H8B	109.5	C17—C19—H19B	109.5
H8A—C8—H8B	109.5	H19A—C19—H19B	109.5
C7—C8—H8C	109.5	C17—C19—H19C	109.5
H8A—C8—H8C	109.5	H19A—C19—H19C	109.5
H8B—C8—H8C	109.5	H19B—C19—H19C	109.5
C7—C9—H9A	109.5	Cl2—C20—Cl1	111.3 (3)
C7—C9—H9B	109.5	Cl2—C20—H20A	109.4
H9A—C9—H9B	109.5	Cl1—C20—H20A	109.4
C7—C9—H9C	109.5	Cl2—C20—H20B	109.4
H9A—C9—H9C	109.5	Cl1—C20—H20B	109.4
H9B—C9—H9C	109.5	H20A—C20—H20B	108.0
C12—N11—C16	124.4 (4)	Cl3—C21—Cl4	112.1 (3)
C12—N11—H11	117.8	Cl3—C21—H21A	109.2
C16—N11—H11	117.8	Cl4—C21—H21A	109.2
N13—C12—N11	115.3 (5)	Cl3—C21—H21B	109.2
N13—C12—Se12	121.1 (4)	Cl4—C21—H21B	109.2
N11—C12—Se12	123.6 (4)	H21A—C21—H21B	107.9

(7) top

Crystal data top

C₇H₁₀I₂N₂OSe	Z = 2
M_r = 470.93	F(000) = 428
Triclinic, P1	D_x = 2.542 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.603 (2) Å	Cell parameters from 1665 reflections
b = 7.700 (3) Å	θ = 2.8–27.0°
c = 13.037 (5) Å	µ = 8.04 mm⁻¹
α = 75.969 (6)°	T = 150 K
β = 86.808 (6)°	Column, red
γ = 73.113 (6)°	0.22 × 0.10 × 0.06 mm
V = 615.3 (7) Å³

Data collection top

Bruker SMART1000 CCD area detector diffractometer	2660 independent reflections
Radiation source: normal-focus sealed tube	1702 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.061
ω scans	θ_max = 27.5°, θ_min = 2.9°
Absorption correction: multi-scan (SHELXTL version 2.10; Bruker, 2003)	h = −8→8
T_min = 0.114, T_max = 0.209	k = −9→9
5463 measured reflections	l = −16→16

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.038	H-atom parameters constrained
wR(F²) = 0.091	w = 1/[σ²(F_o²) + (0.048P)²P] where P = (F_o² + 2F_c²)/3
S = 0.87	(Δ/σ)_max = 0.001
2657 reflections	Δρ_max = 1.26 e Å⁻³
118 parameters	Δρ_min = −1.31 e Å⁻³
0 restraints

Crystal data top

C₇H₁₀I₂N₂OSe	γ = 73.113 (6)°
M_r = 470.93	V = 615.3 (7) Å³
Triclinic, P1	Z = 2
a = 6.603 (2) Å	Mo Kα radiation
b = 7.700 (3) Å	µ = 8.04 mm⁻¹
c = 13.037 (5) Å	T = 150 K
α = 75.969 (6)°	0.22 × 0.10 × 0.06 mm
β = 86.808 (6)°

Data collection top

Bruker SMART1000 CCD area detector diffractometer	2660 independent reflections
Absorption correction: multi-scan (SHELXTL version 2.10; Bruker, 2003)	1702 reflections with I > 2σ(I)
T_min = 0.114, T_max = 0.209	R_int = 0.061
5463 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.091	H-atom parameters constrained
S = 0.87	Δρ_max = 1.26 e Å⁻³
2657 reflections	Δρ_min = −1.31 e Å⁻³
118 parameters

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
I1	0.09128 (7)	0.41491 (6)	0.31637 (3)	0.02543 (14)
I2	0.43796 (8)	0.50358 (7)	0.18987 (4)	0.03713 (17)
Se	−0.22575 (10)	0.31930 (10)	0.44747 (5)	0.02645 (19)
O4	0.4740 (7)	0.0679 (8)	0.6502 (4)	0.0454 (15)
N1	−0.1391 (8)	0.1172 (7)	0.6565 (4)	0.0205 (12)
H1N	−0.2753	0.1273	0.6561	0.025*
C2	−0.0547 (10)	0.1938 (9)	0.5683 (5)	0.0219 (15)
N3	0.1527 (8)	0.1734 (8)	0.5710 (4)	0.0244 (13)
H3N	0.2093	0.2252	0.5133	0.029*
C4	0.2879 (10)	0.0757 (10)	0.6586 (6)	0.0285 (17)
C5	0.1840 (11)	0.0024 (10)	0.7509 (5)	0.0275 (16)
H5	0.2639	−0.0611	0.8143	0.033*
C6	−0.0229 (10)	0.0216 (9)	0.7496 (5)	0.0237 (15)
C7	−0.1515 (10)	−0.0472 (9)	0.8397 (5)	0.0246 (15)
H7A	−0.2483	−0.1040	0.8131	0.029*
H7B	−0.2400	0.0615	0.8651	0.029*
C8	−0.0249 (11)	−0.1896 (10)	0.9333 (5)	0.0309 (17)
H8A	0.0641	−0.2995	0.9092	0.037*
H8B	0.0700	−0.1337	0.9621	0.037*
C9	−0.1684 (13)	−0.2508 (11)	1.0184 (5)	0.044 (2)
H9A	−0.0835	−0.3427	1.0773	0.066*
H9B	−0.2614	−0.3073	0.9901	0.066*
H9C	−0.2544	−0.1424	1.0433	0.066*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.0296 (3)	0.0242 (3)	0.0203 (2)	−0.00775 (19)	0.00053 (19)	−0.00133 (18)
I2	0.0323 (3)	0.0342 (3)	0.0368 (3)	−0.0074 (2)	0.0084 (2)	0.0024 (2)
Se	0.0238 (4)	0.0321 (4)	0.0199 (4)	−0.0080 (3)	−0.0031 (3)	0.0013 (3)
O4	0.023 (3)	0.061 (4)	0.045 (3)	−0.019 (3)	−0.007 (2)	0.012 (3)
N1	0.017 (3)	0.024 (3)	0.018 (3)	−0.004 (2)	−0.001 (2)	−0.001 (2)
C2	0.020 (3)	0.019 (3)	0.024 (4)	−0.005 (3)	0.001 (3)	−0.002 (3)
N3	0.019 (3)	0.026 (3)	0.023 (3)	−0.005 (2)	0.000 (2)	0.001 (3)
C4	0.019 (4)	0.030 (4)	0.034 (4)	−0.008 (3)	−0.008 (3)	0.000 (3)
C5	0.032 (4)	0.028 (4)	0.018 (4)	−0.004 (3)	−0.010 (3)	−0.001 (3)
C6	0.028 (4)	0.020 (4)	0.024 (4)	−0.009 (3)	0.000 (3)	−0.006 (3)
C7	0.026 (4)	0.023 (4)	0.022 (4)	−0.004 (3)	0.001 (3)	−0.004 (3)
C8	0.039 (4)	0.026 (4)	0.024 (4)	−0.010 (3)	0.000 (3)	0.001 (3)
C9	0.068 (6)	0.038 (5)	0.020 (4)	−0.020 (4)	−0.006 (4)	0.009 (3)

Geometric parameters (Å, º) top

I1—Se	2.7807 (11)	C5—H5	0.9500
I1—I2	2.8928 (10)	C6—C7	1.494 (9)
Se—C2	1.876 (6)	C7—C8	1.524 (9)
O4—C4	1.213 (8)	C7—H7A	0.9900
N1—C2	1.331 (8)	C7—H7B	0.9900
N1—C6	1.395 (8)	C8—C9	1.496 (10)
N1—H1N	0.8800	C8—H8A	0.9900
C2—N3	1.334 (8)	C8—H8B	0.9900
N3—C4	1.405 (8)	C9—H9A	0.9800
N3—H3N	0.8800	C9—H9B	0.9800
C4—C5	1.429 (10)	C9—H9C	0.9800
C5—C6	1.332 (9)

Se—I1—I2	176.75 (2)	N1—C6—C7	114.2 (6)
C2—Se—I1	96.9 (2)	C6—C7—C8	115.3 (5)
C2—N1—C6	123.4 (5)	C6—C7—H7A	108.4
C2—N1—H1N	118.3	C8—C7—H7A	108.4
C6—N1—H1N	118.3	C6—C7—H7B	108.4
N1—C2—N3	116.9 (6)	C8—C7—H7B	108.4
N1—C2—Se	119.9 (5)	H7A—C7—H7B	107.5
N3—C2—Se	123.2 (5)	C9—C8—C7	111.0 (6)
C2—N3—C4	125.2 (6)	C9—C8—H8A	109.4
C2—N3—H3N	117.4	C7—C8—H8A	109.4
C4—N3—H3N	117.4	C9—C8—H8B	109.4
O4—C4—N3	118.4 (6)	C7—C8—H8B	109.4
O4—C4—C5	127.1 (6)	H8A—C8—H8B	108.0
N3—C4—C5	114.4 (6)	C8—C9—H9A	109.5
C6—C5—C4	121.1 (6)	C8—C9—H9B	109.5
C6—C5—H5	119.5	H9A—C9—H9B	109.5
C4—C5—H5	119.5	C8—C9—H9C	109.5
C5—C6—N1	119.0 (6)	H9A—C9—H9C	109.5
C5—C6—C7	126.8 (6)	H9B—C9—H9C	109.5

C6—N1—C2—N3	1.1 (9)	N3—C4—C5—C6	2.5 (10)
C6—N1—C2—Se	180.0 (5)	C4—C5—C6—N1	−0.8 (11)
I1—Se—C2—N1	−179.3 (5)	C4—C5—C6—C7	−179.8 (6)
I1—Se—C2—N3	−0.5 (6)	C2—N1—C6—C5	−1.1 (10)
N1—C2—N3—C4	0.9 (10)	C2—N1—C6—C7	178.0 (6)
Se—C2—N3—C4	−177.9 (5)	C5—C6—C7—C8	−14.8 (11)
C2—N3—C4—O4	179.9 (7)	N1—C6—C7—C8	166.2 (6)
C2—N3—C4—C5	−2.7 (10)	C6—C7—C8—C9	−179.3 (6)
O4—C4—C5—C6	179.6 (8)

(9) top

Crystal data top

C₂₄H₂₆N₈O₄Se₂·2(H₂O)	Z = 1
M_r = 684.48	F(000) = 346
Triclinic, P1	D_x = 1.712 Mg m⁻³
a = 4.8330 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.7970 (5) Å	Cell parameters from 2951 reflections
c = 14.1796 (8) Å	θ = 2.9–27.5°
α = 83.490 (3)°	µ = 2.84 mm⁻¹
β = 84.431 (3)°	T = 120 K
γ = 89.353 (3)°	Needle, orange
V = 663.91 (6) Å³	0.20 × 0.04 × 0.03 mm

Data collection top

Bruker Nonius kappaCCD area detector diffractometer	12058 reflections with I > 2σ(I)
Radiation source: FR591 rotating anode	R_int = 0.060
ω and phi scans	θ_max = 27.7°, θ_min = 3.4°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −6→6
T_min = 0.679, T_max = 1.000	k = −12→12
13298 measured reflections	l = −18→18
13281 independent reflections

Refinement top

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)] = 0.084	Hydrogen site location: placed geometrically
wR(F²) = 0.221	Riding model
S = 1.04	w = 1/[σ²(F_o²) + (0.098P)² + 8.436P] where P = (F_o² + 2F_c²)/3
13281 reflections	(Δ/σ)_max = 0.001
182 parameters	Δρ_max = 3.35 e Å⁻³
0 restraints	Δρ_min = −2.06 e Å⁻³

Crystal data top

C₂₄H₂₆N₈O₄Se₂·2(H₂O)	γ = 89.353 (3)°
M_r = 684.48	V = 663.91 (6) Å³
Triclinic, P1	Z = 1
a = 4.8330 (2) Å	Mo Kα radiation
b = 9.7970 (5) Å	µ = 2.84 mm⁻¹
c = 14.1796 (8) Å	T = 120 K
α = 83.490 (3)°	0.20 × 0.04 × 0.03 mm
β = 84.431 (3)°

Data collection top

Bruker Nonius kappaCCD area detector diffractometer	13281 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2003)	12058 reflections with I > 2σ(I)
T_min = 0.679, T_max = 1.000	R_int = 0.060
13298 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.084	0 restraints
wR(F²) = 0.221	Riding model
S = 1.04	Δρ_max = 3.35 e Å⁻³
13281 reflections	Δρ_min = −2.06 e Å⁻³
182 parameters

Special details top

Refinement. The crystal is affected by twinning, principally by a 180 degree rotation about [001].

The water H atoms were not located, but are included in the formula, formula weight, density, mu, etc.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
N1	0.6706 (7)	0.1491 (4)	0.6086 (3)	0.0261 (8)
C2	0.7861 (8)	0.1716 (4)	0.5228 (3)	0.0213 (9)
Se2	0.64806 (8)	0.05982 (4)	0.43430 (3)	0.01942 (13)
N3	0.9985 (7)	0.2698 (4)	0.4937 (3)	0.0237 (8)
C4	1.0998 (8)	0.3449 (4)	0.5642 (3)	0.0228 (8)
O4	1.2814 (7)	0.4333 (4)	0.5408 (2)	0.0368 (8)
C5	0.9727 (8)	0.3122 (5)	0.6585 (3)	0.0264 (9)
H5A	1.0339	0.3578	0.7084	0.032*
C6	0.7679 (8)	0.2185 (4)	0.6795 (3)	0.0250 (9)
C7	0.6138 (9)	0.1823 (5)	0.7756 (3)	0.0296 (10)
H7A	0.5975	0.0810	0.7879	0.035*
H7B	0.4233	0.2203	0.7747	0.035*
C8	0.7477 (10)	0.2343 (5)	0.8576 (3)	0.0360 (11)
H8A	0.6346	0.2063	0.9177	0.054*
H8B	0.7601	0.3347	0.8473	0.054*
H8C	0.9347	0.1953	0.8605	0.054*
N11	0.9880 (7)	0.2203 (4)	0.3389 (3)	0.0267 (8)
C12	1.1022 (9)	0.2925 (5)	0.3959 (3)	0.0258 (9)
N13	1.3078 (7)	0.3826 (4)	0.3670 (3)	0.0281 (8)
H13A	1.3749	0.4291	0.4093	0.034*
C14	1.4195 (9)	0.4051 (4)	0.2715 (3)	0.0230 (9)
O14	1.6106 (6)	0.4878 (3)	0.2466 (2)	0.0305 (7)
C15	1.2867 (9)	0.3226 (5)	0.2087 (3)	0.0300 (10)
H15A	1.3446	0.3320	0.1424	0.036*
C16	1.0852 (9)	0.2345 (5)	0.2442 (3)	0.0269 (10)
C17	0.9424 (9)	0.1403 (5)	0.1876 (3)	0.0298 (10)
H17A	0.7429	0.1651	0.1898	0.036*
H17B	0.9554	0.0452	0.2188	0.036*
C18	1.0575 (13)	0.1433 (6)	0.0841 (4)	0.0494 (15)
H18A	0.9521	0.0793	0.0529	0.074*
H18B	1.2535	0.1159	0.0807	0.074*
H18C	1.0411	0.2364	0.0517	0.074*
O1	0.7388 (8)	0.5170 (5)	0.0441 (3)	0.0554 (11)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0294 (19)	0.0249 (19)	0.025 (2)	0.0052 (15)	−0.0022 (15)	−0.0069 (16)
C2	0.022 (2)	0.0173 (19)	0.025 (2)	−0.0039 (16)	0.0020 (17)	−0.0099 (17)
Se2	0.01854 (19)	0.01570 (19)	0.0238 (2)	−0.00081 (13)	−0.00164 (15)	−0.00138 (16)
N3	0.0214 (17)	0.0253 (19)	0.025 (2)	0.0008 (14)	−0.0017 (14)	−0.0047 (16)
C4	0.028 (2)	0.0216 (19)	0.021 (2)	−0.0046 (16)	−0.0062 (17)	−0.0063 (18)
O4	0.0381 (18)	0.043 (2)	0.0282 (19)	−0.0176 (16)	0.0025 (14)	−0.0013 (16)
C5	0.022 (2)	0.032 (2)	0.025 (2)	0.0013 (18)	−0.0018 (17)	−0.0016 (19)
C6	0.023 (2)	0.026 (2)	0.026 (2)	0.0051 (17)	−0.0062 (17)	−0.0043 (18)
C7	0.028 (2)	0.028 (2)	0.031 (3)	−0.0036 (19)	0.0029 (18)	0.001 (2)
C8	0.038 (3)	0.044 (3)	0.024 (3)	0.005 (2)	0.002 (2)	0.001 (2)
N11	0.0289 (19)	0.0242 (19)	0.029 (2)	−0.0042 (15)	−0.0023 (16)	−0.0111 (16)
C12	0.024 (2)	0.027 (2)	0.025 (2)	0.0049 (18)	−0.0006 (17)	0.0030 (19)
N13	0.030 (2)	0.028 (2)	0.026 (2)	0.0003 (16)	0.0026 (16)	−0.0046 (17)
C14	0.023 (2)	0.022 (2)	0.023 (2)	0.0028 (16)	0.0000 (17)	−0.0016 (18)
O14	0.0297 (16)	0.0353 (18)	0.0252 (18)	−0.0085 (14)	0.0038 (13)	−0.0031 (14)
C15	0.030 (2)	0.032 (2)	0.026 (3)	0.0037 (19)	0.0032 (18)	0.001 (2)
C16	0.024 (2)	0.027 (2)	0.031 (3)	−0.0015 (18)	−0.0012 (18)	−0.012 (2)
C17	0.029 (2)	0.029 (2)	0.033 (3)	−0.0024 (19)	−0.0063 (19)	−0.006 (2)
C18	0.085 (4)	0.038 (3)	0.028 (3)	−0.010 (3)	−0.013 (3)	−0.010 (2)
O1	0.052 (2)	0.078 (3)	0.034 (2)	0.004 (2)	0.0036 (17)	−0.001 (2)

Geometric parameters (Å, º) top

N1—C2	1.284 (5)	C8—H8C	0.9800
N1—C6	1.396 (6)	N11—C12	1.296 (6)
C2—N3	1.414 (5)	N11—C16	1.371 (6)
C2—Se2	1.926 (4)	C12—N13	1.339 (5)
Se2—Se2ⁱ	2.4328 (9)	N13—C14	1.402 (5)
N3—C12	1.423 (6)	N13—H13A	0.8800
N3—C4	1.433 (5)	C14—O14	1.234 (5)
C4—O4	1.235 (5)	C14—C15	1.464 (6)
C4—C5	1.420 (6)	C15—C16	1.331 (6)
C5—C6	1.346 (6)	C15—H15A	0.9500
C5—H5A	0.9500	C16—C17	1.504 (6)
C6—C7	1.496 (6)	C17—C18	1.515 (7)
C7—C8	1.522 (7)	C17—H17A	0.9900
C7—H7A	0.9900	C17—H17B	0.9900
C7—H7B	0.9900	C18—H18A	0.9800
C8—H8A	0.9800	C18—H18B	0.9800
C8—H8B	0.9800	C18—H18C	0.9800

C2—N1—C6	119.2 (4)	C12—N11—C16	118.7 (4)
N1—C2—N3	123.7 (4)	N11—C12—N13	123.6 (4)
N1—C2—Se2	114.7 (3)	N11—C12—N3	116.0 (4)
N3—C2—Se2	121.5 (3)	N13—C12—N3	120.5 (4)
C2—Se2—Se2ⁱ	88.97 (13)	C12—N13—C14	122.0 (4)
C2—N3—C12	119.4 (4)	C12—N13—H13A	119.0
C2—N3—C4	118.5 (4)	C14—N13—H13A	119.0
C12—N3—C4	122.0 (4)	O14—C14—N13	120.9 (4)
O4—C4—C5	124.5 (4)	O14—C14—C15	125.7 (4)
O4—C4—N3	120.1 (4)	N13—C14—C15	113.3 (4)
C5—C4—N3	115.4 (4)	C16—C15—C14	120.3 (4)
C6—C5—C4	122.1 (4)	C16—C15—H15A	119.8
C6—C5—H5A	119.0	C14—C15—H15A	119.8
C4—C5—H5A	119.0	C15—C16—N11	122.1 (4)
C5—C6—N1	121.0 (4)	C15—C16—C17	125.1 (4)
C5—C6—C7	125.6 (4)	N11—C16—C17	112.8 (4)
N1—C6—C7	113.3 (4)	C16—C17—C18	115.1 (4)
C6—C7—C8	114.6 (4)	C16—C17—H17A	108.5
C6—C7—H7A	108.6	C18—C17—H17A	108.5
C8—C7—H7A	108.6	C16—C17—H17B	108.5
C6—C7—H7B	108.6	C18—C17—H17B	108.5
C8—C7—H7B	108.6	H17A—C17—H17B	107.5
H7A—C7—H7B	107.6	C17—C18—H18A	109.5
C7—C8—H8A	109.5	C17—C18—H18B	109.5
C7—C8—H8B	109.5	H18A—C18—H18B	109.5
H8A—C8—H8B	109.5	C17—C18—H18C	109.5
C7—C8—H8C	109.5	H18A—C18—H18C	109.5
H8A—C8—H8C	109.5	H18B—C18—H18C	109.5
H8B—C8—H8C	109.5

Symmetry code: (i) −x+1, −y, −z+1.

(10) top

Crystal data top

C₂₈H₃₄N₈O₄Se₂	Z = 1
M_r = 704.55	F(000) = 358
Triclinic, P1	D_x = 1.660 Mg m⁻³
a = 5.0717 (6) Å	Synchrotron radiation, λ = 0.6775 Å
b = 11.8615 (14) Å	Cell parameters from 1672 reflections
c = 11.9385 (14) Å	θ = 2.2–27.0°
α = 83.161 (2)°	µ = 2.67 mm⁻¹
β = 82.785 (2)°	T = 120 K
γ = 84.358 (2)°	Plate, colourless
V = 704.90 (14) Å³	0.08 × 0.05 × 0.01 mm

Data collection top

Bruker SMART APEXII CCD diffractometer	4198 independent reflections
Radiation source: Daresbury Laboratory Station 9.8	3144 reflections with I > 2σ(I)
Silicon 111 monochromator	R_int = 0.038
fine–slice ω scans	θ_max = 28.9°, θ_min = 2.2°
Absorption correction: multi-scan SADABS version 2.10; Bruker, 2003)	h = −7→7
T_min = 0.804, T_max = 1.000	k = −16→16
8292 measured reflections	l = −17→17

Refinement top

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.097	H-atom parameters constrained
S = 0.98	w = 1/[σ²(F_o²) + (0.0505P)²] where P = (F_o² + 2F_c²)/3
4198 reflections	(Δ/σ)_max = 0.001
190 parameters	Δρ_max = 0.59 e Å⁻³
0 restraints	Δρ_min = −0.92 e Å⁻³

Crystal data top

C₂₈H₃₄N₈O₄Se₂	γ = 84.358 (2)°
M_r = 704.55	V = 704.90 (14) Å³
Triclinic, P1	Z = 1
a = 5.0717 (6) Å	Synchrotron radiation, λ = 0.6775 Å
b = 11.8615 (14) Å	µ = 2.67 mm⁻¹
c = 11.9385 (14) Å	T = 120 K
α = 83.161 (2)°	0.08 × 0.05 × 0.01 mm
β = 82.785 (2)°

Data collection top

Bruker SMART APEXII CCD diffractometer	4198 independent reflections
Absorption correction: multi-scan SADABS version 2.10; Bruker, 2003)	3144 reflections with I > 2σ(I)
T_min = 0.804, T_max = 1.000	R_int = 0.038
8292 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.097	H-atom parameters constrained
S = 0.98	Δρ_max = 0.59 e Å⁻³
4198 reflections	Δρ_min = −0.92 e Å⁻³
190 parameters

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
N1	0.0981 (5)	−0.0445 (2)	0.1979 (2)	0.0214 (5)
C2	0.2181 (6)	0.0405 (2)	0.1429 (3)	0.0210 (6)
Se2	0.14052 (6)	0.07943 (3)	−0.01112 (3)	0.01897 (9)
N3	0.3931 (5)	0.1001 (2)	0.1918 (2)	0.0194 (5)
C4	0.4500 (6)	0.0647 (3)	0.3048 (2)	0.0236 (6)
O4	0.6093 (5)	0.1120 (2)	0.34994 (19)	0.0314 (5)
C5	0.3102 (6)	−0.0281 (3)	0.3613 (3)	0.0245 (6)
H5A	0.3359	−0.0544	0.4378	0.029*
C6	0.1422 (5)	−0.0795 (2)	0.3089 (3)	0.0209 (6)
C7	−0.0107 (6)	−0.1780 (3)	0.3649 (3)	0.0236 (6)
H7A	0.0355	−0.2433	0.3195	0.028*
H7B	−0.2039	−0.1558	0.3640	0.028*
C8	0.0425 (6)	−0.2165 (3)	0.4867 (3)	0.0255 (6)
H8A	−0.0072	−0.1521	0.5329	0.031*
H8B	0.2357	−0.2381	0.4882	0.031*
C9	−0.1119 (7)	−0.3171 (3)	0.5394 (3)	0.0313 (7)
H9A	−0.0665	−0.3402	0.6167	0.047*
H9B	−0.0650	−0.3810	0.4936	0.047*
H9C	−0.3037	−0.2950	0.5419	0.047*
N11	0.4481 (5)	0.2217 (2)	0.0257 (2)	0.0227 (5)
C12	0.5138 (6)	0.1946 (3)	0.1253 (3)	0.0216 (6)
N13	0.6875 (5)	0.2497 (2)	0.1721 (2)	0.0247 (5)
H13A	0.7181	0.2278	0.2427	0.030*
C14	0.8191 (6)	0.3401 (3)	0.1118 (3)	0.0232 (6)
O14	0.9837 (4)	0.3836 (2)	0.15667 (19)	0.0316 (5)
C15	0.7378 (6)	0.3730 (3)	0.0002 (3)	0.0241 (6)
H15A	0.8101	0.4360	−0.0461	0.029*
C16	0.5581 (6)	0.3141 (3)	−0.0391 (3)	0.0232 (6)
C17	0.4620 (6)	0.3411 (3)	−0.1530 (3)	0.0260 (6)
H17B	0.2678	0.3628	−0.1416	0.031*
H17A	0.4877	0.2705	−0.1912	0.031*
C18	0.5926 (6)	0.4350 (3)	−0.2332 (3)	0.0265 (6)
H18A	0.7797	0.4135	−0.2494	0.032*
H18B	0.5728	0.5040	−0.1973	0.032*
C19	0.4659 (7)	0.4554 (3)	−0.3430 (3)	0.0365 (8)
H19A	0.5535	0.5152	−0.3938	0.055*
H19B	0.2758	0.4793	−0.3266	0.055*
H19C	0.4864	0.3848	−0.3796	0.055*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0211 (12)	0.0241 (13)	0.0209 (13)	−0.0053 (9)	−0.0078 (10)	−0.0021 (10)
C2	0.0197 (13)	0.0227 (15)	0.0232 (15)	−0.0029 (10)	−0.0088 (11)	−0.0063 (12)
Se2	0.01838 (14)	0.02263 (15)	0.01808 (14)	−0.00510 (9)	−0.00676 (9)	−0.00343 (10)
N3	0.0212 (12)	0.0220 (12)	0.0175 (12)	−0.0067 (9)	−0.0071 (9)	−0.0033 (10)
C4	0.0268 (15)	0.0265 (16)	0.0191 (15)	−0.0048 (12)	−0.0062 (12)	−0.0026 (12)
O4	0.0373 (13)	0.0372 (13)	0.0244 (12)	−0.0172 (10)	−0.0145 (10)	0.0004 (10)
C5	0.0273 (15)	0.0255 (15)	0.0219 (15)	−0.0055 (11)	−0.0085 (12)	0.0008 (12)
C6	0.0194 (13)	0.0223 (14)	0.0219 (14)	−0.0011 (10)	−0.0057 (11)	−0.0035 (11)
C7	0.0246 (15)	0.0243 (15)	0.0234 (15)	−0.0061 (11)	−0.0079 (12)	−0.0002 (12)
C8	0.0286 (15)	0.0267 (15)	0.0225 (15)	−0.0069 (12)	−0.0075 (12)	0.0011 (12)
C9	0.0329 (17)	0.0331 (18)	0.0293 (17)	−0.0108 (13)	−0.0082 (13)	0.0027 (14)
N11	0.0263 (13)	0.0252 (13)	0.0190 (12)	−0.0076 (10)	−0.0088 (10)	−0.0010 (10)
C12	0.0214 (14)	0.0211 (14)	0.0241 (15)	−0.0047 (11)	−0.0041 (11)	−0.0053 (12)
N13	0.0257 (13)	0.0307 (14)	0.0194 (13)	−0.0083 (10)	−0.0068 (10)	−0.0009 (11)
C14	0.0236 (15)	0.0258 (15)	0.0229 (15)	−0.0075 (11)	−0.0048 (12)	−0.0067 (12)
O14	0.0335 (12)	0.0375 (13)	0.0282 (12)	−0.0185 (10)	−0.0093 (10)	−0.0026 (10)
C15	0.0223 (14)	0.0232 (15)	0.0279 (16)	−0.0075 (11)	−0.0032 (12)	−0.0026 (13)
C16	0.0201 (14)	0.0243 (15)	0.0258 (15)	−0.0036 (11)	−0.0043 (11)	−0.0024 (12)
C17	0.0244 (15)	0.0321 (17)	0.0229 (15)	−0.0094 (12)	−0.0034 (12)	−0.0017 (13)
C18	0.0283 (16)	0.0278 (16)	0.0240 (16)	−0.0076 (12)	−0.0043 (12)	−0.0002 (13)
C19	0.046 (2)	0.039 (2)	0.0265 (17)	−0.0169 (16)	−0.0099 (15)	0.0041 (15)

Geometric parameters (Å, º) top

N1—C2	1.296 (4)	C9—H9C	0.9800
N1—C6	1.379 (4)	N11—C12	1.272 (4)
C2—N3	1.407 (3)	N11—C16	1.386 (4)
C2—Se2	1.921 (3)	C12—N13	1.356 (3)
Se2—Se2ⁱ	2.4427 (6)	N13—C14	1.396 (4)
N3—C4	1.421 (4)	N13—H13A	0.8800
N3—C12	1.437 (4)	C14—O14	1.230 (3)
C4—O4	1.236 (3)	C14—C15	1.443 (4)
C4—C5	1.423 (4)	C15—C16	1.360 (4)
C5—C6	1.348 (4)	C15—H15A	0.9500
C5—H5A	0.9500	C16—C17	1.491 (4)
C6—C7	1.509 (4)	C17—C18	1.526 (4)
C7—C8	1.520 (4)	C17—H17B	0.9900
C7—H7A	0.9900	C17—H17A	0.9900
C7—H7B	0.9900	C18—C19	1.515 (4)
C8—C9	1.522 (4)	C18—H18A	0.96
C8—H8A	0.9900	C18—H18B	0.96
C8—H8B	0.9900	C19—H19A	0.9800
C9—H9A	0.9800	C19—H19B	0.9800
C9—H9B	0.9800	C19—H19C	0.9800

C2—N1—C6	119.6 (2)	C12—N11—C16	118.2 (2)
N1—C2—N3	122.6 (3)	N11—C12—N13	124.1 (3)
N1—C2—Se2	115.2 (2)	N11—C12—N3	117.2 (2)
N3—C2—Se2	122.2 (2)	N13—C12—N3	118.6 (3)
C2—Se2—Se2ⁱ	89.43 (9)	C12—N13—C14	122.1 (3)
C2—N3—C4	119.6 (2)	C12—N13—H13A	119.0
C2—N3—C12	119.0 (2)	C14—N13—H13A	119.0
C4—N3—C12	121.4 (2)	O14—C14—N13	119.3 (3)
O4—C4—N3	121.9 (3)	O14—C14—C15	127.1 (3)
O4—C4—C5	123.0 (3)	N13—C14—C15	113.6 (2)
N3—C4—C5	115.1 (2)	C16—C15—C14	120.2 (3)
C6—C5—C4	121.6 (3)	C16—C15—H15A	119.9
C6—C5—H5A	119.2	C14—C15—H15A	119.9
C4—C5—H5A	119.2	C15—C16—N11	121.7 (3)
C5—C6—N1	121.4 (3)	C15—C16—C17	124.3 (3)
C5—C6—C7	123.7 (3)	N11—C16—C17	114.0 (2)
N1—C6—C7	114.9 (2)	C16—C17—C18	117.0 (2)
C6—C7—C8	114.3 (2)	C16—C17—H17B	108.1
C6—C7—H7A	108.7	C18—C17—H17B	108.1
C8—C7—H7A	108.7	C16—C17—H17A	108.1
C6—C7—H7B	108.7	C18—C17—H17A	108.1
C8—C7—H7B	108.7	H17B—C17—H17A	107.3
H7A—C7—H7B	107.6	C19—C18—C17	110.5 (3)
C7—C8—C9	112.6 (2)	C19—C18—H18A	111
C7—C8—H8A	109.1	C17—C18—H18A	110
C9—C8—H8A	109.1	C19—C18—H18B	110
C7—C8—H8B	109.1	C17—C18—H18B	109
C9—C8—H8B	109.1	H18A—C18—H18B	108
H8A—C8—H8B	107.8	C18—C19—H19A	109.5
C8—C9—H9A	109.5	C18—C19—H19B	109.5
C8—C9—H9B	109.5	H19A—C19—H19B	109.5
H9A—C9—H9B	109.5	C18—C19—H19C	109.5
C8—C9—H9C	109.5	H19A—C19—H19C	109.5
H9A—C9—H9C	109.5	H19B—C19—H19C	109.5
H9B—C9—H9C	109.5

Symmetry code: (i) −x, −y, −z.

(11) top

Crystal data top

C₇H₁₀N₂O₂	F(000) = 1476
M_r = 154.17	D_x = 1.352 Mg m⁻³
Rhombohedral, R3	Mo Kα radiation, λ = 0.71073 Å
a = 19.9444 (10) Å	Cell parameters from 1748 reflections
c = 9.8918 (10) Å	θ = 2.4–27.4°
α = 90°	µ = 0.10 mm⁻¹
γ = 120°	T = 150 K
V = 3407.6 (10) Å³	Lens, orange
Z = 18	0.52 × 0.17 × 0.17 mm

Data collection top

Bruker SMART APEX CCD area detector diffractometer	1297 reflections with I > 2σ(I)
Radiation source: normal-focus sealed tube	R_int = 0.039
Graphite monochromator	θ_max = 27.5°, θ_min = 2.0°
ω scans	h = −25→19
5827 measured reflections	k = −24→25
1750 independent reflections	l = −11→12

Refinement top

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.131	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0725P)²] where P = (F_o² + 2F_c²)/3
1750 reflections	(Δ/σ)_max = 0.001
100 parameters	Δρ_max = 0.45 e Å⁻³
0 restraints	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₇H₁₀N₂O₂	V = 3407.6 (10) Å³
M_r = 154.17	Z = 18
Rhombohedral, R3	Mo Kα radiation
a = 19.9444 (10) Å	µ = 0.10 mm⁻¹
c = 9.8918 (10) Å	T = 150 K
α = 90°	0.52 × 0.17 × 0.17 mm
γ = 120°

Data collection top

Bruker SMART APEX CCD area detector diffractometer	1297 reflections with I > 2σ(I)
5827 measured reflections	R_int = 0.039
1750 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.131	H-atom parameters constrained
S = 1.05	Δρ_max = 0.45 e Å⁻³
1750 reflections	Δρ_min = −0.16 e Å⁻³
100 parameters

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
N1	0.44496 (7)	0.43728 (6)	0.14328 (13)	0.0258 (3)
H1A	0.4950	0.4707	0.1438	0.031*
C2	0.39503 (8)	0.46548 (8)	0.14184 (15)	0.0246 (3)
O2	0.41748 (6)	0.53514 (5)	0.14432 (11)	0.0312 (3)
N3	0.31833 (6)	0.41060 (7)	0.14000 (12)	0.0247 (3)
H3A	0.2848	0.4270	0.1363	0.030*
C4	0.28878 (8)	0.33105 (8)	0.14348 (16)	0.0239 (3)
O4	0.21781 (5)	0.28696 (6)	0.14833 (11)	0.0302 (3)
C5	0.34551 (8)	0.30687 (8)	0.14229 (15)	0.0242 (4)
H5A	0.3292	0.2532	0.1403	0.029*
C6	0.42145 (8)	0.35933 (8)	0.14395 (15)	0.0230 (3)
C7	0.48678 (8)	0.34221 (8)	0.14507 (16)	0.0273 (4)
H7A	0.5217	0.3708	0.2212	0.033*
H7B	0.5168	0.3626	0.0605	0.033*
C8	0.46339 (9)	0.25734 (8)	0.15790 (17)	0.0299 (4)
H8A	0.4372	0.2372	0.2458	0.036*
H8B	0.4263	0.2274	0.0852	0.036*
C9	0.53339 (10)	0.24658 (9)	0.1483 (2)	0.0435 (5)
H9A	0.5167	0.1915	0.1567	0.065*
H9B	0.5698	0.2755	0.2211	0.065*
H9C	0.5589	0.2658	0.0607	0.065*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0171 (6)	0.0197 (6)	0.0390 (8)	0.0079 (5)	−0.0004 (5)	0.0011 (5)
C2	0.0220 (7)	0.0226 (7)	0.0291 (9)	0.0111 (6)	0.0000 (6)	0.0007 (6)
O2	0.0241 (5)	0.0202 (5)	0.0491 (7)	0.0110 (4)	−0.0020 (5)	0.0004 (5)
N3	0.0189 (6)	0.0208 (6)	0.0351 (8)	0.0105 (5)	−0.0007 (5)	0.0003 (5)
C4	0.0231 (7)	0.0213 (7)	0.0272 (8)	0.0111 (6)	0.0006 (6)	−0.0006 (6)
O4	0.0190 (5)	0.0219 (5)	0.0466 (7)	0.0080 (4)	0.0018 (4)	−0.0013 (5)
C5	0.0243 (7)	0.0199 (7)	0.0287 (9)	0.0113 (6)	0.0008 (6)	−0.0001 (6)
C6	0.0240 (7)	0.0201 (7)	0.0250 (8)	0.0112 (6)	−0.0006 (6)	−0.0002 (6)
C7	0.0212 (7)	0.0242 (7)	0.0366 (9)	0.0114 (6)	−0.0017 (6)	−0.0006 (6)
C8	0.0270 (8)	0.0253 (8)	0.0408 (10)	0.0156 (7)	0.0004 (7)	0.0001 (6)
C9	0.0341 (9)	0.0307 (9)	0.0716 (13)	0.0206 (7)	0.0018 (9)	0.0003 (8)

Geometric parameters (Å, º) top

N1—C2	1.3670 (17)	N1—H1A	0.88
N1—C6	1.3812 (16)	N3—H3A	0.88
C2—O2	1.2286 (16)	C5—H5A	0.95
C2—N3	1.3652 (17)	C7—H7A	0.99
N3—C4	1.3894 (17)	C7—H7B	0.99
C4—O4	1.2387 (16)	C8—H8A	0.99
C4—C5	1.4348 (18)	C8—H8B	0.99
C5—C6	1.3432 (18)	C9—H9A	0.98
C6—C7	1.5031 (19)	C9—H9B	0.98
C7—C8	1.5195 (19)	C9—H9C	0.98
C8—C9	1.518 (2)

C2—N1—C6	123.79 (11)	C4—C5—H5A	120
O2—C2—N3	122.39 (12)	C6—C5—H5A	120
O2—C2—N1	122.45 (12)	C6—C7—H7A	108
N3—C2—N1	115.14 (11)	C6—C7—H7B	108
C2—N3—C4	125.50 (11)	C8—C7—H7A	108
O4—C4—N3	119.57 (12)	C8—C7—H7B	108
O4—C4—C5	125.09 (12)	H7A—C7—H7B	107
N3—C4—C5	115.34 (11)	C7—C8—H8A	109
C6—C5—C4	120.64 (12)	C7—C8—H8B	109
C5—C6—N1	119.51 (12)	C9—C8—H8A	109
C5—C6—C7	126.23 (12)	C9—C8—H8B	109
N1—C6—C7	114.26 (11)	H8A—C8—H8B	108
C6—C7—C8	115.82 (12)	C8—C9—H9A	109
C9—C8—C7	111.13 (13)	C8—C9—H9B	110
C6—N1—H1A	118	C8—C9—H9C	110
C2—N1—H1A	118	H9A—C9—H9B	110
C2—N3—H3A	117	H9A—C9—H9C	109
C4—N3—H3A	117	H9B—C9—H9C	109

Experimental details

	(1)	(2)	(3)	(4)
Crystal data
Chemical formula	C₅H₆N₂OSe	C₆H₈N₂OSe	C₇H₁₀N₂OSe	C₇H₁₀N₂OSe
M_r	189.08	203.10	217.13	217.13
Crystal system, space group	Monoclinic, P2₁/c	Triclinic, P1	Orthorhombic, Pbca	Triclinic, P1
Temperature (K)	120	150	120	150
a, b, c (Å)	4.3411 (7), 14.756 (2), 9.690 (2)	8.394 (2), 10.029 (2), 14.931 (4)	10.568 (7), 11.257 (7), 28.79 (2)	8.9192 (9), 10.6403 (10), 15.1965 (15)
α, β, γ (°)	90, 90.157 (2), 90	101.023 (4), 100.893 (4), 105.705 (4)	90, 90, 90	106.019 (2), 105.366 (2), 96.166 (2)
V (Å³)	620.71 (18)	1148.5 (5)	3425 (4)	1311.0 (2)
Z	4	6	16	6
Radiation type	Synchrotron, λ = 0.6775 Å	Mo Kα	Synchrotron, λ = 0.6775 Å	Mo Kα
µ (mm⁻¹)	5.96	4.84	4.33	4.24
Crystal size (mm)	0.10 × 0.01 × 0.01	0.21 × 0.12 × 0.04	0.20 × 0.02 × 0.01	0.25 × 0.14 × 0.06

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer	Bruker SMART APEX CCD area detector diffractometer	Bruker SMART APEXII CCD diffractometer	Bruker SMART APEX CCD area detector diffractometer
Absorption correction	Multi-scan (SADABS version 2.10; Bruker, 2003)	Multi-scan (SADABS version 2.03; Bruker, 2001)	Multi-scan (SADABS; Bruker, 2004)	Multi-scan Bruker SADABS v2.03
T_min, T_max	0.816, 1.000	0.687, 1.000	0.260, 1.000	0.581, 0.770
No. of measured, independent and observed [I > 2σ(I)] reflections	6350, 1770, 1642	8174, 4025, 3189	24855, 3471, 2417	8163, 5780, 4932
R_int	0.027	0.038	0.250	0.013
(sin θ/λ)_max (Å⁻¹)	0.716	0.596	0.624	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.025, 0.074, 0.80	0.056, 0.146, 1.03	0.173, 0.408, 1.18	0.028, 0.071, 1.04
No. of reflections	1770	4025	3471	5780
No. of parameters	83	271	99	298
No. of restraints	0	69	35	0
H-atom treatment	Rigid rotating group; riding model	H-atom parameters constrained	H-atom parameters constrained	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.57, −0.80	1.48, −1.02	2.38, −2.33	0.65, −0.40

	(4.CH2Cl2)	(7)	(9)	(10)
Crystal data
Chemical formula	C₈H₁₂Cl₂N₂OSe	C₇H₁₀I₂N₂OSe	C₂₄H₂₆N₈O₄Se₂·2(H₂O)	C₂₈H₃₄N₈O₄Se₂
M_r	302.06	470.93	684.48	704.55
Crystal system, space group	Triclinic, P1	Triclinic, P1	Triclinic, P1	Triclinic, P1
Temperature (K)	150	150	120	120
a, b, c (Å)	8.841 (3), 11.259 (3), 12.424 (4)	6.603 (2), 7.700 (3), 13.037 (5)	4.8330 (2), 9.7970 (5), 14.1796 (8)	5.0717 (6), 11.8615 (14), 11.9385 (14)
α, β, γ (°)	90.450 (5), 105.350 (4), 92.945 (5)	75.969 (6), 86.808 (6), 73.113 (6)	83.490 (3), 84.431 (3), 89.353 (3)	83.161 (2), 82.785 (2), 84.358 (2)
V (Å³)	1190.7 (6)	615.3 (7)	663.91 (6)	704.90 (14)
Z	4	2	1	1
Radiation type	Mo Kα	Mo Kα	Mo Kα	Synchrotron, λ = 0.6775 Å
µ (mm⁻¹)	3.57	8.04	2.84	2.67
Crystal size (mm)	0.36 × 0.22 × 0.02	0.22 × 0.10 × 0.06	0.20 × 0.04 × 0.03	0.08 × 0.05 × 0.01

Data collection
Diffractometer	Bruker SMART APEX CCD area detector diffractometer	Bruker SMART1000 CCD area detector diffractometer	Bruker Nonius kappaCCD area detector diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (TWINABS version 1.02; Bruker, 2001)	Multi-scan (SHELXTL version 2.10; Bruker, 2003)	Multi-scan (SADABS; Bruker, 2003)	Multi-scan SADABS version 2.10; Bruker, 2003)
T_min, T_max	0.684, 1.000	0.114, 0.209	0.679, 1.000	0.804, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	10743, 6193, 4391	5463, 2660, 1702	13298, 13281, 12058	8292, 4198, 3144
R_int	0.050	0.061	0.060	0.038
(sin θ/λ)_max (Å⁻¹)	0.650	0.650	0.654	0.714

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.099, 0.97	0.038, 0.091, 0.87	0.084, 0.221, 1.04	0.042, 0.097, 0.98
No. of reflections	6193	2657	13281	4198
No. of parameters	254	118	182	190
No. of restraints	0	0	0	0
H-atom treatment	H-atom parameters constrained	H-atom parameters constrained	Riding model	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.87, −0.51	1.26, −1.31	3.35, −2.06	0.59, −0.92

	(11)
Crystal data
Chemical formula	C₇H₁₀N₂O₂
M_r	154.17
Crystal system, space group	Rhombohedral, R3
Temperature (K)	150
a, b, c (Å)	19.9444 (10), 19.9444 (10), 9.8918 (10)
α, β, γ (°)	90, 90, 120
V (Å³)	3407.6 (10)
Z	18
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.52 × 0.17 × 0.17

Data collection
Diffractometer	Bruker SMART APEX CCD area detector diffractometer
Absorption correction	–
T_min, T_max	–
No. of measured, independent and observed [I > 2σ(I)] reflections	5827, 1750, 1297
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.131, 1.05
No. of reflections	1750
No. of parameters	100
No. of restraints	0
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.16

Computer programs: Bruker APEX2 (Bruker, 2004), Bruker SMART version 5.625 (Bruker, 2001), Bruker SMART version 5.624 (Bruker, 2001), COLLECT (Hooft, 1998), Bruker APEX2, Bruker SAINT (Bruker, 2004), Bruker SAINT version 6.36a (Bruker, 2000), Bruker SAINT version 6.36a (Bruker, 2001), DIRAX (Duisenberg, 1992), Bruker SAINT; Bruker SHELXTL (Bruker, 2001), Bruker SAINT; Bruker SHELXTL, HKL (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 1990), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), enCIFer (Allen et al., 2004); PLATON, enCIFer (Allen et al., 2004; PLATON).

Hydrogen-bond geometry (Å, º) for (4) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O1Bⁱ	0.88	1.91	2.782 (3)	169
N1A—H1AA···O1	0.88	2.00	2.860 (3)	167
N1B—H1BA···O1Aⁱⁱ	0.88	1.92	2.796 (3)	177
N1—H1A···Se1ⁱⁱⁱ	0.88	2.60	3.460 (2)	165
N3B—H3BA···Se1ⁱ	0.88	2.56	3.428 (2)	167
N3A—H3AA···Se1Bⁱⁱ	0.88	2.60	3.430 (2)	157

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

Footnotes

¹Supplementary data for this paper are available from the IUCr electronic archives (Reference: SO5003 ). Services for accessing these data are described at the back of the journal.

Acknowledgements

We thank the Marie Curie Foundation for funding (to CDA) as part of the Marie Curie Host Fellowship HPMT-CT-2001-00376 COSMIC, and the graduate program in Bioinorganic Chemistry based at Ioannina, Greece and coordinated by NH. We thank EPSRC (UK) for the award of diffractometers and for data collection by the EPSRC National Service for Crystallography at the University of Southampton, UK, and at the Daresbury Laboratory Synchrotron Radiation Source. MS acknowledges receipt of a Royal Society–Leverhulme Trust Senior Research Fellowship and of a Royal Society Wolfson Merit Award.

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Volume 62| Part 4| August 2006| Pages 580-591

doi:10.1107/S0108768106011426