5,12-Diselena-3,4,13,14-tetra­aza­tri­cyclo[9.3.0.0^2,6]tetra­deca-3,13-diene

The title compound, C₈H₈N₄Se₂, crystallizes in a non-symmetrical conformation with a dihedral angle between the heterocycles of 45.0 (3)° and a nearly strain-free tetra­methyl­ene tether. The crystal studied was non-merohedrally twinned with a fractional contribution of 0.342 (3) for the minor twin component.

Key indicators

• Single-crystal X-ray study
• T = 120 K
• Mean [sigma](C-C) = 0.014 Å
• R factor = 0.065
• wR factor = 0.217
• Data-to-parameter ratio = 52.9

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTY02_ALERT_1_C  An _exptl_absorpt_correction_type has been given without
            a literature citation. This should be contained in the
            _exptl_absorpt_process_details field.
            Absorption correction given as integration
PLAT341_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.01388 Ang.
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         17 Report
PLAT918_ALERT_3_C Reflection(s) with I(obs) much Smaller I(calc) .         26 Check
PLAT939_ALERT_3_C Large Value of Not (SHELXL) Weight Optimized S .      22.02 Check

Alert level G
PLAT072_ALERT_2_G SHELXL First  Parameter in WGHT  Unusually Large       0.12 Report
PLAT870_ALERT_4_G ALERTS Related to Twinning Effects Suppressed ..          ! Info
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         41 Note
PLAT931_ALERT_5_G CIFcalcFCF  Twin Law ( 1 1 0)         Est.d BASF       0.49 Check
PLAT931_ALERT_5_G CIFcalcFCF  Twin Law ( 1-1-2)         Est.d BASF       0.43 Check
PLAT931_ALERT_5_G CIFcalcFCF  Twin Law ( 1-1-1)         Est.d BASF       0.37 Check

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

   1 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
   5 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   3 ALERT type 5 Informative message, check

---

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).

5,12-Diselena-3,4,13,14-tetraazatricyclo[9.3.0.0^2,6]tetradeca-3,13-diene

Crystal data

C8H8N4Se2	Z = 2
Mr = 318.10	F(000) = 304
Triclinic, P1	Dx = 2.220 Mg m^−3
a = 7.5350 (18) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.6723 (17) Å	Cell parameters from 5222 reflections
c = 9.372 (2) Å	θ = 3.0–28.6°
α = 90.136 (18)°	µ = 7.73 mm^−1
β = 90.773 (19)°	T = 120 K
γ = 118.555 (17)°	Needle, brown
V = 475.8 (2) Å^3	0.45 × 0.23 × 0.22 mm

Data collection

Stoe IPDS 2T diffractometer	6775 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	5946 reflections with I > 2σ(I)
Detector resolution: 6.67 pixels mm^-1	Rint = 0.046
rotation method scans	θmax = 28.3°, θmin = 3.0°
Absorption correction: integration	h = −9→9
Tmin = 0.093, Tmax = 0.252	k = −10→10
6775 measured reflections	l = −12→12

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.065	H-atom parameters constrained
wR(F^2) = 0.217	w = 1/[σ^2(Fo^2) + (0.1209P)^2 + 3.1505P] where P = (Fo^2 + 2Fc^2)/3
S = 1.12	(Δ/σ)max < 0.001
6775 reflections	Δρmax = 1.68 e Å^−3
128 parameters	Δρmin = −1.50 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. Refined as a 2-component twin.

Hydrogen atoms attached to carbons were placed at calculated positions and were refined in the riding-model approximation with C–H = 0.95 Å, and with U_iso(H) = 1.2 U_eq(C).

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

	x	y	z	Uiso*/Ueq
Se1	0.71557 (14)	0.29021 (14)	0.56893 (9)	0.0299 (3)
N2	0.4663 (14)	0.1129 (13)	0.6483 (9)	0.0330 (17)
N3	0.3899 (14)	0.2082 (12)	0.7102 (8)	0.0300 (16)
C4	0.4967 (13)	0.4132 (13)	0.7084 (8)	0.0219 (15)
C5	0.6788 (13)	0.4941 (14)	0.6393 (8)	0.0245 (16)
C6	0.8389 (16)	0.7040 (16)	0.6103 (10)	0.0323 (19)
H6A	0.864929	0.714893	0.506599	0.039*
H6B	0.965074	0.725639	0.659402	0.039*
C7	0.7975 (16)	0.8732 (15)	0.6540 (9)	0.0309 (18)
H7A	0.653666	0.832240	0.633311	0.037*
H7B	0.879991	0.989880	0.594356	0.037*
C8	0.8430 (14)	0.9360 (14)	0.8119 (9)	0.0262 (16)
H8A	0.988852	0.985256	0.831092	0.031*
H8B	0.814767	1.047758	0.828919	0.031*
C9	0.7226 (14)	0.7718 (14)	0.9176 (8)	0.0257 (16)
H9A	0.772439	0.673575	0.917303	0.031*
H9B	0.743231	0.829398	1.014935	0.031*
C10	0.5016 (13)	0.6699 (13)	0.8799 (8)	0.0222 (15)
Se11	0.31509 (15)	0.73496 (15)	0.95420 (9)	0.0304 (3)
N12	0.1178 (13)	0.5308 (14)	0.8370 (9)	0.0327 (16)
N13	0.1976 (12)	0.4468 (13)	0.7656 (8)	0.0277 (15)
C14	0.4026 (13)	0.5159 (14)	0.7841 (8)	0.0233 (16)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Se1	0.0262 (5)	0.0322 (5)	0.0348 (5)	0.0169 (4)	0.0023 (4)	−0.0034 (4)
N2	0.034 (5)	0.028 (4)	0.035 (4)	0.013 (4)	0.011 (3)	0.004 (3)
N3	0.033 (4)	0.026 (4)	0.027 (3)	0.011 (4)	0.005 (3)	0.000 (3)
C4	0.023 (4)	0.023 (4)	0.019 (3)	0.010 (3)	−0.002 (3)	−0.002 (3)
C5	0.021 (4)	0.029 (4)	0.023 (3)	0.012 (4)	0.001 (3)	−0.002 (3)
C6	0.030 (5)	0.033 (5)	0.032 (4)	0.014 (4)	0.009 (4)	−0.001 (4)
C7	0.031 (5)	0.032 (5)	0.028 (4)	0.014 (4)	0.005 (3)	0.004 (3)
C8	0.023 (4)	0.025 (4)	0.026 (3)	0.007 (4)	0.002 (3)	−0.004 (3)
C9	0.020 (4)	0.031 (4)	0.020 (3)	0.008 (4)	0.003 (3)	−0.002 (3)
C10	0.022 (4)	0.022 (4)	0.021 (3)	0.009 (3)	0.004 (3)	−0.001 (3)
Se11	0.0275 (5)	0.0315 (5)	0.0321 (5)	0.0138 (4)	0.0066 (4)	−0.0050 (4)
N12	0.021 (4)	0.038 (5)	0.036 (4)	0.012 (4)	0.002 (3)	−0.003 (3)
N13	0.019 (4)	0.034 (4)	0.027 (3)	0.011 (3)	0.003 (3)	0.001 (3)
C14	0.021 (4)	0.028 (4)	0.020 (3)	0.011 (4)	0.001 (3)	0.000 (3)

Geometric parameters (Å, º)

Se1—C5	1.837 (9)	C7—H7B	0.9900
Se1—N2	1.879 (9)	C8—C9	1.526 (12)
N2—N3	1.269 (11)	C8—H8A	0.9900
N3—C4	1.383 (12)	C8—H8B	0.9900
C4—C5	1.378 (13)	C9—C10	1.499 (12)
C4—C14	1.473 (11)	C9—H9A	0.9900
C5—C6	1.509 (14)	C9—H9B	0.9900
C6—C7	1.529 (13)	C10—C14	1.376 (12)
C6—H6A	0.9900	C10—Se11	1.845 (8)
C6—H6B	0.9900	Se11—N12	1.895 (9)
C7—C8	1.538 (12)	N12—N13	1.267 (11)
C7—H7A	0.9900	N13—C14	1.381 (11)
C5—Se1—N2	87.9 (4)	C9—C8—C7	114.7 (8)
N3—N2—Se1	110.2 (7)	C9—C8—H8A	108.6
N2—N3—C4	117.8 (8)	C7—C8—H8A	108.6
C5—C4—N3	115.8 (8)	C9—C8—H8B	108.6
C5—C4—C14	128.7 (8)	C7—C8—H8B	108.6
N3—C4—C14	115.5 (8)	H8A—C8—H8B	107.6
C4—C5—C6	133.7 (8)	C10—C9—C8	111.1 (6)
C4—C5—Se1	108.3 (7)	C10—C9—H9A	109.4
C6—C5—Se1	118.0 (6)	C8—C9—H9A	109.4
C5—C6—C7	118.1 (8)	C10—C9—H9B	109.4
C5—C6—H6A	107.8	C8—C9—H9B	109.4
C7—C6—H6A	107.8	H9A—C9—H9B	108.0
C5—C6—H6B	107.8	C14—C10—C9	126.9 (8)
C7—C6—H6B	107.8	C14—C10—Se11	108.1 (6)
H6A—C6—H6B	107.1	C9—C10—Se11	125.0 (6)
C6—C7—C8	114.7 (7)	C10—Se11—N12	87.4 (4)
C6—C7—H7A	108.6	N13—N12—Se11	110.3 (6)
C8—C7—H7A	108.6	N12—N13—C14	117.5 (8)
C6—C7—H7B	108.6	C10—C14—N13	116.6 (8)
C8—C7—H7B	108.6	C10—C14—C4	124.8 (8)
H7A—C7—H7B	107.6	N13—C14—C4	118.5 (8)
C5—Se1—N2—N3	0.2 (6)	C8—C9—C10—Se11	−94.1 (8)
Se1—N2—N3—C4	0.1 (9)	C14—C10—Se11—N12	0.0 (6)
N2—N3—C4—C5	−0.5 (11)	C9—C10—Se11—N12	179.1 (7)
N2—N3—C4—C14	−178.9 (7)	C10—Se11—N12—N13	0.2 (6)
N3—C4—C5—C6	179.1 (8)	Se11—N12—N13—C14	−0.4 (10)
C14—C4—C5—C6	−2.7 (14)	C9—C10—C14—N13	−179.3 (7)
N3—C4—C5—Se1	0.6 (8)	Se11—C10—C14—N13	−0.2 (9)
C14—C4—C5—Se1	178.8 (6)	C9—C10—C14—C4	4.8 (13)
N2—Se1—C5—C4	−0.4 (6)	Se11—C10—C14—C4	−176.1 (6)
N2—Se1—C5—C6	−179.2 (7)	N12—N13—C14—C10	0.4 (11)
C4—C5—C6—C7	−5.1 (14)	N12—N13—C14—C4	176.6 (7)
Se1—C5—C6—C7	173.2 (6)	C5—C4—C14—C10	−46.0 (12)
C5—C6—C7—C8	82.6 (11)	N3—C4—C14—C10	132.3 (9)
C6—C7—C8—C9	−59.7 (11)	C5—C4—C14—N13	138.2 (8)
C7—C8—C9—C10	−49.6 (10)	N3—C4—C14—N13	−43.6 (10)
C8—C9—C10—C14	84.9 (10)