rac-4H,5H,6H,7H,8H,9H,10H,11H-Cyclo­deca­[d][1,2,3]selena­diazol-4-ol

Schollmeyer, D.; Detert, H.

doi:10.1107/S2414314626000957

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 11| Part 2| February 2026| x260095

https://doi.org/10.1107/S2414314626000957

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rac-4H,5H,6H,7H,8H,9H,10H,11H-Cyclodeca[d][1,2,3]selenadiazol-4-ol

Dieter Schollmeyer ^a and Heiner Detert ^a ^*

^aUniversity of Mainz, Department of Chemistry, Duesbergweg 10-14, 55099 Mainz, Germany
^*Correspondence e-mail: [email protected]

Edited by M. Bolte, Goethe-Universität Frankfurt, Germany (Received 27 January 2026; accepted 29 January 2026; online 5 February 2026)

Two molecules of the title compound, C₁₀H₁₆N₂OSe, with a chair conformation are connected via hydrogen bonds into centrosymmetric dimers. C—H⋯O hydrogen bonds interconnect the dimers.

Keywords: crystal structure; heterocycle; selenium; medium-sized ring; hydrogen bond.

CCDC reference: 2526821

Structure description

The title compound, C₁₀H₁₆N₂OSe (Fig. 1), was prepared in a project focusing on transannular cyclizations (Detert et al., 1992 ; Krämer et al., 2009 ; Meier et al.,) in medium-sized cycloalkynes (Detert & Schollmeyer, 2021 ; Herges et al., 2005 ). The molecule adopts a chair conformation. There are two planes, one is the heterocycle and adjacent C atoms (C5, C12), the other is composed of C5, C6, C7 and C10, C11, C12. The former is planar within 0.0357 (16) Å at C5, the latter within 0.1002 (17) Å at C7. Both planes are close to orthogonal, making a dihedral angle of 85.02 (5)°. The methylene groups CH₂-8, CH₂-9 are staggered. In the crystal, pairs of molecules form centrosymmetric dimers, connected via O14—H14⋯N3ⁱ hydrogen bonds (Table 1, Fig. 2). The molecules of the dimers are connected to neighbouring molecules, one via a c-glide plane, the other one via translation along the c-axis. For details of the C—H⋯O hydrogen bonds connecting the dimers, see Table 1.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12B⋯O14ⁱ	0.99	2.58	3.430 (2)	144
O14—H14⋯N3ⁱⁱ	0.78 (3)	2.22 (3)	2.9801 (18)	165 (2)
C11—H11A⋯O14ⁱⁱⁱ	0.99	2.56	3.419 (2)	145
Symmetry codes: (i) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (ii) ; (iii) .

Figure 1
View of the title compound. Displacement ellipsoids are drawn at the 50% probability level.

Figure 2
Part of the packing diagram. Hydrogen bonds are drawn with dashed lines. View along c-axis direction. Only hydrogen atoms involved in hydrogen bonds are shown for clarity.

Synthesis and crystallization

The sample was prepared from sebacoin (Prelog et al., 1947 ; Rühlmann, 1971 ) via acetylation (Carlson & Bateman 1967 ), formation and oxidation of its semicarbazone and deacetylation with 2-aminoethanol, m.p. 418 K. Crystallization was by slow evaporation of a solution in methanol/dichloromethane. ¹H-NMR (250 MHz, CDCl₃): 5.18 (dd, 1 H, 4-H), 3.24 (m, 2H), 2.18-2.43 (m, 3 H), 1.58-1.90 (m, 2H), 1.15-1.55 (m, 8 H). ¹³C-NMR (100 MHz, CDCl₃): 161.96 (C-3a, ²J_C—Se = 27 Hz), 161.34 (C-11a, ¹J_C—Se = 135 Hz), 67.53 (C-4), 38.78 (C-11), 30.32, 26.94, 25.04, 24.21, 21.88, 19.70. ⁷⁷Se-NMR (76.3 MHz, CDCl₃): 1525.8 p.p.m. (Me₂Se = 0).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₀H₁₆N₂OSe
M_r	259.21
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	120
a, b, c (Å)	11.3765 (5), 12.3700 (4), 7.6033 (3)
β (°)	103.747 (3)
V (Å³)	1039.34 (7)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	3.58
Crystal size (mm)	0.35 × 0.32 × 0.08

Data collection
Diffractometer	Stoe Stadivari
Absorption correction	Integration [X-RED32 (Stoe & Cie, 2020 ), absorption correction by Gaussian integration, analogous to Coppens (1970 )]
T_min, T_max	0.672, 0.911
No. of measured, independent and observed [I > 2σ(I)] reflections	9011, 2636, 2338
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.671

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.025, 0.068, 1.08
No. of reflections	2636
No. of parameters	131
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.63, −0.43
Computer programs: X-AREA WinXpose, Recipe and Integrate (Stoe & Cie, 2020), SHELXT2014 (Sheldrick, 2015a ), SHELXL2019/2 (Sheldrick, 2015b ) and PLATON (Spek, 2009 ).

Structural data

CCDC reference: 2526821

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S2414314626000957/bt4197sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314626000957/bt4197Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314626000957/bt4197Isup3.cml

checkCIF report

Computing details top

rac-4H,5H,6H,7H,8H,9H,10H,11H-Cyclodeca[d][1,2,3]selenadiazol-4-ol top

Crystal data top

C₁₀H₁₆N₂OSe	D_x = 1.657 Mg m⁻³
M_r = 259.21	Melting point: 418 K
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.3765 (5) Å	Cell parameters from 15860 reflections
b = 12.3700 (4) Å	θ = 2.5–33.7°
c = 7.6033 (3) Å	µ = 3.58 mm⁻¹
β = 103.747 (3)°	T = 120 K
V = 1039.34 (7) Å³	Plate, brown
Z = 4	0.35 × 0.32 × 0.08 mm
F(000) = 528

Data collection top

Stoe Stadivari diffractometer	2636 independent reflections
Radiation source: Axo Mo	2338 reflections with I > 2σ(I)
Detector resolution: 13.33 pixels mm^-1	R_int = 0.023
rotation method, ω scans	θ_max = 28.5°, θ_min = 2.5°
Absorption correction: integration [X-Red32 (Stoe & Cie, 2020), absorption correction by Gaussian integration, analogous to Coppens (1970)]	h = −15→15
T_min = 0.672, T_max = 0.911	k = −16→16
9011 measured reflections	l = −10→10

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.025	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.068	w = 1/[σ²(F_o²) + (0.0454P)² + 0.0208P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max = 0.001
2636 reflections	Δρ_max = 0.63 e Å⁻³
131 parameters	Δρ_min = −0.43 e Å⁻³
0 restraints

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Hydrogen atoms attached to carbons were placed at calculated positions and were refined in the riding-model approximation with C_methylene–H = 0.99 Å, C_tertiary–H = 1.00 Å, and with U_iso(H) = 1.2 U_eq(C). Hydrogen atom H14 attached to O14 was refined isotropically.

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

	x	y	z	U_iso*/U_eq
Se1	0.45006 (2)	0.68523 (2)	0.48407 (2)	0.01632 (7)
N2	0.54559 (12)	0.60029 (12)	0.37125 (19)	0.0175 (3)
N3	0.48019 (12)	0.55443 (11)	0.23022 (18)	0.0148 (3)
C4	0.35750 (14)	0.57504 (12)	0.1901 (2)	0.0128 (3)
C5	0.28163 (15)	0.52610 (13)	0.0178 (2)	0.0143 (3)
H5	0.195907	0.548864	0.007480	0.017*
C6	0.28386 (16)	0.40234 (13)	0.0134 (2)	0.0179 (3)
H6A	0.365938	0.379757	0.005564	0.021*
H6B	0.227068	0.378654	−0.099816	0.021*
C7	0.25231 (16)	0.34018 (14)	0.1707 (2)	0.0185 (3)
H7A	0.303042	0.369285	0.285035	0.022*
H7B	0.276149	0.263773	0.161795	0.022*
C8	0.12010 (16)	0.34178 (15)	0.1858 (3)	0.0206 (4)
H8A	0.068247	0.320765	0.066855	0.025*
H8B	0.110468	0.285582	0.274041	0.025*
C9	0.07213 (15)	0.44839 (14)	0.2427 (2)	0.0182 (3)
H9A	−0.012947	0.437897	0.249508	0.022*
H9B	0.072662	0.503203	0.148010	0.022*
C10	0.14468 (14)	0.49220 (13)	0.4253 (2)	0.0157 (3)
H10A	0.113867	0.458365	0.523539	0.019*
H10B	0.230420	0.470593	0.442049	0.019*
C11	0.13838 (15)	0.61496 (14)	0.4428 (2)	0.0182 (3)
H11A	0.182414	0.635982	0.566559	0.022*
H11B	0.052684	0.636301	0.427624	0.022*
C12	0.19156 (15)	0.67821 (12)	0.3053 (2)	0.0154 (3)
H12A	0.139014	0.667721	0.182503	0.018*
H12B	0.191917	0.756274	0.334065	0.018*
C13	0.31837 (14)	0.64318 (13)	0.3054 (2)	0.0132 (3)
O14	0.31845 (12)	0.56888 (10)	−0.13529 (16)	0.0180 (3)
H14	0.379 (2)	0.542 (2)	−0.143 (3)	0.037 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Se1	0.01354 (10)	0.01686 (11)	0.01669 (11)	−0.00094 (6)	−0.00010 (7)	−0.00468 (6)
N2	0.0136 (6)	0.0191 (7)	0.0192 (7)	0.0020 (6)	0.0030 (5)	0.0000 (6)
N3	0.0138 (6)	0.0145 (7)	0.0156 (7)	0.0008 (5)	0.0028 (5)	0.0003 (6)
C4	0.0141 (7)	0.0106 (7)	0.0134 (7)	−0.0012 (6)	0.0029 (6)	0.0017 (6)
C5	0.0146 (7)	0.0148 (8)	0.0125 (7)	0.0012 (6)	0.0010 (6)	0.0007 (6)
C6	0.0209 (8)	0.0148 (8)	0.0174 (8)	−0.0005 (7)	0.0033 (7)	−0.0038 (7)
C7	0.0201 (8)	0.0134 (8)	0.0216 (8)	0.0011 (7)	0.0040 (7)	0.0002 (7)
C8	0.0194 (8)	0.0178 (8)	0.0232 (9)	−0.0039 (7)	0.0019 (7)	−0.0023 (7)
C9	0.0148 (7)	0.0197 (8)	0.0196 (8)	−0.0017 (7)	0.0028 (6)	0.0006 (7)
C10	0.0136 (8)	0.0185 (8)	0.0144 (7)	0.0009 (6)	0.0024 (6)	0.0025 (6)
C11	0.0166 (8)	0.0196 (8)	0.0189 (8)	0.0013 (6)	0.0051 (7)	0.0001 (7)
C12	0.0140 (8)	0.0150 (8)	0.0162 (8)	0.0010 (6)	0.0019 (6)	−0.0007 (6)
C13	0.0136 (7)	0.0103 (7)	0.0146 (7)	−0.0027 (6)	0.0012 (6)	0.0003 (6)
O14	0.0214 (6)	0.0183 (6)	0.0147 (6)	0.0046 (5)	0.0048 (5)	0.0027 (5)

Geometric parameters (Å, º) top

Se1—C13	1.8418 (16)	C8—H8A	0.9900
Se1—N2	1.8612 (14)	C8—H8B	0.9900
N2—N3	1.2830 (19)	C9—C10	1.536 (2)
N3—C4	1.380 (2)	C9—H9A	0.9900
C4—C13	1.365 (2)	C9—H9B	0.9900
C4—C5	1.513 (2)	C10—C11	1.527 (2)
C5—O14	1.4294 (19)	C10—H10A	0.9900
C5—C6	1.532 (2)	C10—H10B	0.9900
C5—H5	1.0000	C11—C12	1.540 (2)
C6—C7	1.534 (2)	C11—H11A	0.9900
C6—H6A	0.9900	C11—H11B	0.9900
C6—H6B	0.9900	C12—C13	1.506 (2)
C7—C8	1.536 (2)	C12—H12A	0.9900
C7—H7A	0.9900	C12—H12B	0.9900
C7—H7B	0.9900	O14—H14	0.78 (3)
C8—C9	1.528 (2)

C13—Se1—N2	87.85 (7)	H8A—C8—H8B	107.3
N3—N2—Se1	110.41 (11)	C8—C9—C10	114.14 (14)
N2—N3—C4	117.28 (13)	C8—C9—H9A	108.7
C13—C4—N3	116.05 (14)	C10—C9—H9A	108.7
C13—C4—C5	126.66 (14)	C8—C9—H9B	108.7
N3—C4—C5	117.17 (14)	C10—C9—H9B	108.7
O14—C5—C4	109.85 (13)	H9A—C9—H9B	107.6
O14—C5—C6	110.03 (13)	C11—C10—C9	113.78 (14)
C4—C5—C6	114.20 (13)	C11—C10—H10A	108.8
O14—C5—H5	107.5	C9—C10—H10A	108.8
C4—C5—H5	107.5	C11—C10—H10B	108.8
C6—C5—H5	107.5	C9—C10—H10B	108.8
C5—C6—C7	118.40 (14)	H10A—C10—H10B	107.7
C5—C6—H6A	107.7	C10—C11—C12	114.32 (14)
C7—C6—H6A	107.7	C10—C11—H11A	108.7
C5—C6—H6B	107.7	C12—C11—H11A	108.7
C7—C6—H6B	107.7	C10—C11—H11B	108.7
H6A—C6—H6B	107.1	C12—C11—H11B	108.7
C6—C7—C8	117.81 (15)	H11A—C11—H11B	107.6
C6—C7—H7A	107.9	C13—C12—C11	112.58 (14)
C8—C7—H7A	107.9	C13—C12—H12A	109.1
C6—C7—H7B	107.9	C11—C12—H12A	109.1
C8—C7—H7B	107.9	C13—C12—H12B	109.1
H7A—C7—H7B	107.2	C11—C12—H12B	109.1
C9—C8—C7	117.02 (15)	H12A—C12—H12B	107.8
C9—C8—H8A	108.0	C4—C13—C12	129.46 (14)
C7—C8—H8A	108.0	C4—C13—Se1	108.42 (11)
C9—C8—H8B	108.0	C12—C13—Se1	122.04 (12)
C7—C8—H8B	108.0	C5—O14—H14	109.8 (18)

C13—Se1—N2—N3	−0.03 (12)	C7—C8—C9—C10	−57.3 (2)
Se1—N2—N3—C4	−0.13 (17)	C8—C9—C10—C11	153.10 (15)
N2—N3—C4—C13	0.3 (2)	C9—C10—C11—C12	−62.33 (19)
N2—N3—C4—C5	176.55 (14)	C10—C11—C12—C13	−52.79 (19)
C13—C4—C5—O14	113.06 (17)	N3—C4—C13—C12	−177.09 (15)
N3—C4—C5—O14	−62.74 (18)	C5—C4—C13—C12	7.1 (3)
C13—C4—C5—C6	−122.78 (18)	N3—C4—C13—Se1	−0.29 (17)
N3—C4—C5—C6	61.42 (18)	C5—C4—C13—Se1	−176.14 (13)
O14—C5—C6—C7	177.50 (14)	C11—C12—C13—C4	99.6 (2)
C4—C5—C6—C7	53.4 (2)	C11—C12—C13—Se1	−76.78 (16)
C5—C6—C7—C8	70.6 (2)	N2—Se1—C13—C4	0.18 (12)
C6—C7—C8—C9	−70.8 (2)	N2—Se1—C13—C12	177.26 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12B···O14ⁱ	0.99	2.58	3.430 (2)	144
O14—H14···N3ⁱⁱ	0.78 (3)	2.22 (3)	2.9801 (18)	165 (2)
C11—H11A···O14ⁱⁱⁱ	0.99	2.56	3.419 (2)	145

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

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