rac-11-Selena-12,13-di­aza­bicyclo­[10.3.0]penta­deca-10a(13a),12-dien-1-ol

The title compound, C₁₂H₂₀N₂OSe, crystallizes in strands of enanti­omeric mol­ecules connected via O—H...N hydrogen bonds. There are only slight deviations from an ideal gauche conformation in the deca­methyl­ene chain, indicating just a little strain.

Key indicators

• Single-crystal X-ray study
• T = 193 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.029
• wR factor = 0.070
• Data-to-parameter ratio = 14.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          8 Report
PLAT918_ALERT_3_C Reflection(s) with I(obs) much Smaller I(calc) .          1 Check

Alert level G
PLAT063_ALERT_4_G Crystal Size Possibly too Large for Beam Size ..       0.71 mm
PLAT164_ALERT_4_G Nr. of Refined C-H H-Atoms in Heavy-Atom Struct.         19 Note
PLAT793_ALERT_4_G Model has Chirality at C12         (Centro SPGR)          R Verify
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          2 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         17 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          4 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   2 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   6 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: X-AREA WinXpose (Stoe & Cie, 2019); cell refinement: X-AREA Recipe (Stoe & Cie, 2019); data reduction: X-AREA Integrate (Stoe & Cie, 2019); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2020).

rac-11-Selena-12,13-diazabicyclo[10.3.0]pentadeca-10a(13a),12-dien-1-ol

Crystal data

C12H20N2OSe	F(000) = 592
Mr = 287.26	Dx = 1.493 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.9261 (5) Å	Cell parameters from 9207 reflections
b = 19.9277 (9) Å	θ = 2.6–28.4°
c = 7.3829 (4) Å	µ = 2.92 mm^−1
β = 103.321 (4)°	T = 193 K
V = 1277.91 (12) Å^3	Block, colourless
Z = 4	0.71 × 0.26 × 0.20 mm

Data collection

Stoe IPDS 2T diffractometer	3020 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	2721 reflections with I > 2σ(I)
Detector resolution: 6.67 pixels mm^-1	Rint = 0.017
rotation method, ω scans	θmax = 27.9°, θmin = 2.6°
Absorption correction: integration [X-Red32 (Stoe & Cie, 2019), absorption correction by Gaussian integration, analogous to Coppens (1970)]	h = −11→10
Tmin = 0.294, Tmax = 0.601	k = −24→26
6412 measured reflections	l = −9→9

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.029	All H-atom parameters refined
wR(F^2) = 0.070	w = 1/[σ^2(Fo^2) + (0.0304P)^2 + 0.7552P] where P = (Fo^2 + 2Fc^2)/3
S = 1.14	(Δ/σ)max = 0.001
3020 reflections	Δρmax = 0.41 e Å^−3
216 parameters	Δρmin = −0.67 e Å^−3
0 restraints

Special details

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 were refined with isotropic displacement parameters constraining the Us of two H atoms bonded to the same C atom to the same value.

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

	x	y	z	Uiso*/Ueq
Se1	0.82417 (2)	0.15493 (2)	0.75710 (3)	0.03612 (8)
C2	0.6550 (2)	0.16090 (9)	0.5593 (2)	0.0263 (3)
C3	0.6625 (2)	0.15035 (10)	0.3601 (3)	0.0296 (4)
H3A	0.755 (3)	0.1703 (11)	0.344 (3)	0.034 (4)*
H3B	0.579 (3)	0.1750 (12)	0.279 (3)	0.034 (4)*
C4	0.6544 (3)	0.07597 (12)	0.3019 (3)	0.0389 (5)
H4A	0.687 (3)	0.0747 (13)	0.183 (4)	0.044 (5)*
H4B	0.730 (3)	0.0518 (13)	0.394 (4)	0.044 (5)*
C5	0.4957 (3)	0.04424 (11)	0.2800 (3)	0.0378 (5)
H5A	0.462 (3)	0.0536 (13)	0.390 (4)	0.046 (5)*
H5B	0.499 (3)	−0.0049 (14)	0.271 (4)	0.046 (5)*
C6	0.3781 (3)	0.06857 (11)	0.1084 (3)	0.0348 (4)
H6A	0.372 (3)	0.1168 (12)	0.112 (3)	0.034 (4)*
H6B	0.420 (3)	0.0588 (11)	0.000 (3)	0.034 (4)*
C7	0.2171 (3)	0.03777 (13)	0.0816 (3)	0.0470 (6)
H7A	0.221 (3)	−0.0077 (15)	0.071 (4)	0.058 (6)*
H7B	0.149 (3)	0.0529 (14)	−0.043 (4)	0.058 (6)*
C8	0.1357 (3)	0.05394 (12)	0.2377 (3)	0.0459 (5)
H8A	0.200 (3)	0.0389 (14)	0.359 (4)	0.056 (6)*
H8B	0.040 (3)	0.0265 (14)	0.224 (4)	0.056 (6)*
C9	0.0886 (2)	0.12727 (13)	0.2466 (3)	0.0388 (5)
H9A	0.151 (3)	0.1562 (12)	0.186 (4)	0.041 (5)*
H9B	−0.010 (3)	0.1333 (13)	0.172 (4)	0.041 (5)*
C10	0.0892 (2)	0.15211 (12)	0.4425 (3)	0.0356 (4)
H10A	0.049 (3)	0.1978 (14)	0.435 (3)	0.042 (5)*
H10B	0.016 (3)	0.1240 (13)	0.494 (3)	0.042 (5)*
C11	0.2460 (2)	0.15032 (10)	0.5800 (3)	0.0286 (4)
H11A	0.282 (3)	0.1034 (13)	0.606 (3)	0.036 (4)*
H11B	0.238 (3)	0.1680 (12)	0.694 (4)	0.036 (4)*
C12	0.36991 (19)	0.19034 (9)	0.5151 (2)	0.0235 (3)
H12	0.372 (2)	0.1780 (10)	0.388 (3)	0.019 (5)*
C13	0.52951 (19)	0.17624 (9)	0.6290 (2)	0.0229 (3)
N14	0.55574 (18)	0.18287 (8)	0.8195 (2)	0.0273 (3)
N15	0.6932 (2)	0.17459 (9)	0.9149 (2)	0.0337 (4)
O16	0.33526 (16)	0.26009 (7)	0.52548 (19)	0.0298 (3)
H16	0.385 (3)	0.2790 (13)	0.471 (4)	0.042 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Se1	0.02420 (11)	0.05973 (15)	0.02309 (11)	0.00772 (8)	0.00266 (7)	0.00148 (8)
C2	0.0242 (8)	0.0346 (9)	0.0195 (8)	0.0024 (7)	0.0041 (6)	0.0016 (6)
C3	0.0259 (9)	0.0447 (11)	0.0199 (8)	0.0060 (8)	0.0087 (7)	0.0013 (7)
C4	0.0465 (12)	0.0474 (12)	0.0247 (9)	0.0209 (10)	0.0122 (8)	−0.0004 (8)
C5	0.0617 (14)	0.0285 (10)	0.0255 (9)	0.0074 (9)	0.0147 (9)	0.0011 (7)
C6	0.0507 (12)	0.0313 (10)	0.0237 (9)	−0.0019 (8)	0.0116 (8)	−0.0038 (7)
C7	0.0634 (15)	0.0433 (13)	0.0350 (11)	−0.0173 (11)	0.0127 (10)	−0.0138 (10)
C8	0.0552 (13)	0.0454 (13)	0.0395 (12)	−0.0232 (11)	0.0162 (10)	−0.0096 (9)
C9	0.0289 (10)	0.0558 (13)	0.0286 (9)	−0.0081 (9)	0.0002 (8)	−0.0025 (9)
C10	0.0237 (9)	0.0506 (12)	0.0325 (10)	−0.0025 (8)	0.0063 (7)	−0.0029 (8)
C11	0.0244 (8)	0.0383 (10)	0.0235 (8)	−0.0032 (7)	0.0061 (7)	−0.0013 (7)
C12	0.0227 (8)	0.0293 (9)	0.0191 (7)	0.0020 (6)	0.0060 (6)	−0.0017 (6)
C13	0.0239 (8)	0.0269 (8)	0.0183 (7)	−0.0003 (6)	0.0058 (6)	−0.0006 (6)
N14	0.0288 (7)	0.0346 (8)	0.0187 (7)	0.0013 (6)	0.0059 (6)	−0.0008 (6)
N15	0.0319 (8)	0.0479 (10)	0.0204 (7)	0.0047 (7)	0.0042 (6)	0.0000 (6)
O16	0.0314 (7)	0.0297 (7)	0.0303 (7)	0.0044 (5)	0.0113 (5)	0.0029 (5)

Geometric parameters (Å, º)

Se1—C2	1.8467 (18)	C8—C9	1.526 (4)
Se1—N15	1.8723 (17)	C8—H8A	0.99 (3)
C2—C13	1.371 (2)	C8—H8B	1.00 (3)
C2—C3	1.502 (2)	C9—C10	1.528 (3)
C3—C4	1.540 (3)	C9—H9A	0.98 (3)
C3—H3A	0.95 (2)	C9—H9B	0.93 (3)
C3—H3B	0.97 (2)	C10—C11	1.529 (3)
C4—C5	1.525 (3)	C10—H10A	0.98 (3)
C4—H4A	0.99 (3)	C10—H10B	1.00 (3)
C4—H4B	0.97 (3)	C11—C12	1.527 (2)
C5—C6	1.526 (3)	C11—H11A	0.99 (2)
C5—H5A	0.94 (3)	C11—H11B	0.93 (3)
C5—H5B	0.98 (3)	C12—O16	1.430 (2)
C6—C7	1.533 (3)	C12—C13	1.505 (2)
C6—H6A	0.96 (2)	C12—H12	0.97 (2)
C6—H6B	0.97 (2)	C13—N14	1.378 (2)
C7—C8	1.532 (3)	N14—N15	1.276 (2)
C7—H7A	0.91 (3)	O16—H16	0.77 (3)
C7—H7B	1.03 (3)
C2—Se1—N15	87.97 (7)	C9—C8—H8A	111.0 (17)
C13—C2—C3	128.55 (16)	C7—C8—H8A	109.7 (17)
C13—C2—Se1	107.90 (12)	C9—C8—H8B	106.9 (17)
C3—C2—Se1	123.55 (13)	C7—C8—H8B	110.7 (17)
C2—C3—C4	113.45 (16)	H8A—C8—H8B	103 (2)
C2—C3—H3A	107.5 (14)	C8—C9—C10	114.19 (19)
C4—C3—H3A	110.8 (14)	C8—C9—H9A	110.9 (14)
C2—C3—H3B	109.0 (14)	C10—C9—H9A	111.2 (16)
C4—C3—H3B	109.5 (14)	C8—C9—H9B	109.3 (16)
H3A—C3—H3B	106 (2)	C10—C9—H9B	108.2 (16)
C5—C4—C3	114.30 (16)	H9A—C9—H9B	102 (2)
C5—C4—H4A	110.8 (15)	C9—C10—C11	115.09 (17)
C3—C4—H4A	105.5 (15)	C9—C10—H10A	109.0 (15)
C5—C4—H4B	110.2 (15)	C11—C10—H10A	109.2 (15)
C3—C4—H4B	107.5 (15)	C9—C10—H10B	108.6 (15)
H4A—C4—H4B	108 (2)	C11—C10—H10B	108.1 (14)
C4—C5—C6	113.62 (17)	H10A—C10—H10B	107 (2)
C4—C5—H5A	107.3 (16)	C12—C11—C10	113.45 (16)
C6—C5—H5A	110.8 (16)	C12—C11—H11A	109.0 (14)
C4—C5—H5B	112.2 (16)	C10—C11—H11A	111.0 (14)
C6—C5—H5B	106.6 (15)	C12—C11—H11B	107.5 (15)
H5A—C5—H5B	106 (2)	C10—C11—H11B	109.8 (15)
C5—C6—C7	115.13 (19)	H11A—C11—H11B	106 (2)
C5—C6—H6A	108.9 (14)	O16—C12—C13	109.89 (14)
C7—C6—H6A	110.5 (14)	O16—C12—C11	108.02 (14)
C5—C6—H6B	107.3 (14)	C13—C12—C11	112.81 (14)
C7—C6—H6B	109.7 (14)	O16—C12—H12	110.3 (12)
H6A—C6—H6B	104.7 (19)	C13—C12—H12	105.6 (12)
C8—C7—C6	114.35 (18)	C11—C12—H12	110.2 (12)
C8—C7—H7A	107.9 (19)	C2—C13—N14	116.31 (15)
C6—C7—H7A	110.7 (19)	C2—C13—C12	125.62 (15)
C8—C7—H7B	109.3 (17)	N14—C13—C12	117.96 (14)
C6—C7—H7B	109.9 (16)	N15—N14—C13	117.79 (15)
H7A—C7—H7B	104 (2)	N14—N15—Se1	110.03 (12)
C9—C8—C7	114.6 (2)	C12—O16—H16	107 (2)
N15—Se1—C2—C13	0.38 (14)	C10—C11—C12—C13	−167.50 (16)
N15—Se1—C2—C3	−179.79 (17)	C3—C2—C13—N14	179.73 (18)
C13—C2—C3—C4	−96.5 (2)	Se1—C2—C13—N14	−0.5 (2)
Se1—C2—C3—C4	83.7 (2)	C3—C2—C13—C12	−4.2 (3)
C2—C3—C4—C5	72.5 (2)	Se1—C2—C13—C12	175.63 (14)
C3—C4—C5—C6	71.9 (2)	O16—C12—C13—C2	−108.7 (2)
C4—C5—C6—C7	−179.99 (18)	C11—C12—C13—C2	130.74 (19)
C5—C6—C7—C8	62.7 (3)	O16—C12—C13—N14	67.4 (2)
C6—C7—C8—C9	68.6 (3)	C11—C12—C13—N14	−53.2 (2)
C7—C8—C9—C10	−149.0 (2)	C2—C13—N14—N15	0.3 (3)
C8—C9—C10—C11	62.1 (3)	C12—C13—N14—N15	−176.12 (17)
C9—C10—C11—C12	57.0 (2)	C13—N14—N15—Se1	0.1 (2)
C10—C11—C12—O16	70.83 (19)	C2—Se1—N15—N14	−0.26 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O16—H16···N14^i	0.77 (3)	2.22 (3)	2.976 (2)	170 (3)

Symmetry code: (i) x, −y+1/2, z−1/2.