4-Benzyl-1,2,4-tri­aza­spiro­[4.5]dec-1-ene-3-thione

In the title compound, C₁₄H₁₇N₃S, the cyclo­hexane ring adopts a chair conformation. The dihedral angle between the triazole and phenyl ring is 77.2 (3)°. In the crystal structure, C—H...S hydrogen link mol­ecules into C(7) chains along the b-axis direction. The crystal studied was refined as as an inversion twin.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.056
• wR factor = 0.138
• Data-to-parameter ratio = 15.9

checkCIF/PLATON results

No syntax errors found



Alert level C
STRVA01_ALERT_4_C           Flack test results are ambiguous.
           From the CIF: _refine_ls_abs_structure_Flack    0.320
           From the CIF: _refine_ls_abs_structure_Flack_su    0.040
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00738 Ang.

Alert level G
PLAT033_ALERT_4_G Flack x Value Deviates > 3.0 * sigma from Zero .      0.320 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          8 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          2 Note

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


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

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Computing details

Data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 2012).

4-Benzyl-1,2,4-triazaspiro[4.5]dec-1-ene-3-thione

Crystal data

C14H17N3S	Dx = 1.268 Mg m^−3
Mr = 259.36	Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, P212121	Cell parameters from 1528 reflections
a = 7.3730 (6) Å	θ = 4.8–68.8°
b = 10.7698 (7) Å	µ = 1.99 mm^−1
c = 17.1056 (12) Å	T = 173 K
V = 1358.28 (17) Å^3	Irregular, colourless
Z = 4	0.34 × 0.32 × 0.22 mm
F(000) = 552

Data collection

Rigaku Oxford Diffraction diffractometer	2607 independent reflections
Radiation source: Enhance (Cu) X-ray Source	1974 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.071
Detector resolution: 16.0416 pixels mm^-1	θmax = 71.7°, θmin = 4.9°
ω scans	h = −9→8
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	k = −11→13
Tmin = 0.531, Tmax = 1.000	l = −20→20
8805 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.056	w = 1/[σ^2(Fo^2) + (0.062P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.138	(Δ/σ)max < 0.001
S = 1.02	Δρmax = 0.29 e Å^−3
2607 reflections	Δρmin = −0.28 e Å^−3
164 parameters	Absolute structure: Flack (1983), 1097 Friedel pairs; refined as an inversion twin
0 restraints	Absolute structure parameter: 0.32 (4)

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 two-component inversion twin

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

	x	y	z	Uiso*/Ueq
C1	0.5544 (7)	0.2039 (4)	0.4292 (2)	0.0379 (10)
C2	0.5495 (7)	0.4171 (4)	0.4180 (2)	0.0341 (9)
C3	0.7193 (7)	0.4963 (4)	0.4071 (3)	0.0384 (11)
H3A	0.823318	0.452406	0.428091	0.046*
H3B	0.740128	0.509365	0.351664	0.046*
C4	0.7017 (8)	0.6217 (5)	0.4477 (3)	0.0433 (13)
H4A	0.699621	0.609261	0.503813	0.052*
H4B	0.806647	0.672345	0.435208	0.052*
C5	0.5310 (7)	0.6895 (4)	0.4229 (3)	0.0446 (12)
H5A	0.521308	0.766687	0.451853	0.053*
H5B	0.538792	0.709806	0.367735	0.053*
C6	0.3633 (8)	0.6119 (5)	0.4372 (3)	0.0471 (13)
H6A	0.257830	0.656208	0.418029	0.056*
H6B	0.348178	0.599756	0.493036	0.056*
C7	0.3741 (7)	0.4850 (4)	0.3969 (3)	0.0405 (12)
H7A	0.271087	0.434823	0.412623	0.049*
H7B	0.368257	0.496254	0.340741	0.049*
C8	0.5758 (7)	0.2799 (4)	0.2940 (2)	0.0386 (11)
H8A	0.493986	0.337892	0.268686	0.046*
H8B	0.535983	0.196663	0.280833	0.046*
C9	0.7632 (7)	0.2991 (4)	0.2621 (3)	0.0356 (11)
C10	0.7936 (8)	0.3828 (4)	0.2015 (3)	0.0418 (12)
H10	0.696770	0.427247	0.180833	0.050*
C11	0.9654 (9)	0.4006 (5)	0.1718 (3)	0.0486 (14)
H11	0.983486	0.456565	0.131170	0.058*
C12	1.1088 (8)	0.3366 (5)	0.2017 (3)	0.0525 (15)
H12	1.224866	0.349381	0.182015	0.063*
C13	1.0808 (7)	0.2528 (5)	0.2612 (3)	0.0588 (15)
H13	1.178518	0.208316	0.281210	0.071*
C14	0.9102 (7)	0.2340 (5)	0.2915 (3)	0.0455 (12)
H14	0.893503	0.177266	0.331846	0.055*
N1	0.5623 (6)	0.2963 (3)	0.37830 (19)	0.0346 (8)
N2	0.5381 (6)	0.3770 (3)	0.5009 (2)	0.0423 (10)
N3	0.5407 (6)	0.2617 (4)	0.5075 (2)	0.0455 (10)
S1	0.5585 (2)	0.05329 (10)	0.41790 (8)	0.0495 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.036 (2)	0.039 (2)	0.039 (2)	0.000 (2)	0.001 (3)	−0.0023 (19)
C2	0.040 (3)	0.034 (2)	0.028 (2)	0.0020 (19)	0.006 (2)	−0.0013 (16)
C3	0.040 (3)	0.039 (2)	0.036 (3)	0.000 (2)	0.001 (2)	−0.002 (2)
C4	0.057 (4)	0.034 (3)	0.039 (3)	−0.008 (2)	0.001 (2)	0.000 (2)
C5	0.062 (3)	0.026 (2)	0.045 (3)	0.000 (2)	0.003 (3)	−0.003 (2)
C6	0.053 (3)	0.037 (3)	0.051 (3)	0.011 (2)	0.010 (3)	−0.001 (2)
C7	0.043 (3)	0.038 (2)	0.041 (3)	−0.001 (2)	0.003 (2)	0.001 (2)
C8	0.039 (3)	0.043 (3)	0.033 (2)	0.002 (2)	−0.007 (2)	−0.0043 (19)
C9	0.041 (3)	0.034 (2)	0.032 (2)	−0.001 (2)	0.000 (2)	−0.0073 (19)
C10	0.056 (3)	0.037 (3)	0.033 (3)	0.006 (2)	−0.007 (2)	0.000 (2)
C11	0.067 (4)	0.048 (3)	0.031 (2)	−0.013 (3)	0.005 (3)	−0.001 (2)
C12	0.046 (4)	0.062 (4)	0.050 (3)	−0.007 (3)	0.014 (3)	−0.003 (3)
C13	0.036 (3)	0.062 (3)	0.079 (4)	0.010 (3)	0.000 (3)	0.013 (3)
C14	0.043 (3)	0.047 (3)	0.046 (3)	0.005 (2)	0.004 (2)	0.011 (2)
N1	0.041 (2)	0.0309 (18)	0.0317 (18)	−0.0008 (19)	0.0009 (19)	−0.0007 (14)
N2	0.058 (3)	0.037 (2)	0.0324 (19)	−0.001 (2)	0.005 (2)	−0.0029 (17)
N3	0.060 (3)	0.041 (2)	0.036 (2)	−0.002 (2)	0.006 (2)	−0.0008 (17)
S1	0.0572 (8)	0.0316 (6)	0.0597 (8)	−0.0043 (6)	0.0020 (8)	−0.0025 (6)

Geometric parameters (Å, º)

C1—N1	1.324 (5)	C7—H7A	0.9700
C1—N3	1.481 (5)	C7—H7B	0.9700
C1—S1	1.634 (4)	C8—N1	1.456 (5)
C2—N1	1.470 (5)	C8—C9	1.500 (7)
C2—N2	1.485 (5)	C8—H8A	0.9700
C2—C3	1.527 (7)	C8—H8B	0.9700
C2—C7	1.528 (7)	C9—C14	1.386 (7)
C3—C4	1.524 (6)	C9—C10	1.391 (6)
C3—H3A	0.9700	C10—C11	1.378 (8)
C3—H3B	0.9700	C10—H10	0.9300
C4—C5	1.516 (7)	C11—C12	1.362 (8)
C4—H4A	0.9700	C11—H11	0.9300
C4—H4B	0.9700	C12—C13	1.376 (7)
C5—C6	1.512 (7)	C12—H12	0.9300
C5—H5A	0.9700	C13—C14	1.375 (7)
C5—H5B	0.9700	C13—H13	0.9300
C6—C7	1.533 (6)	C14—H14	0.9300
C6—H6A	0.9700	N2—N3	1.247 (5)
C6—H6B	0.9700
N1—C1—N3	106.4 (4)	C2—C7—H7A	109.4
N1—C1—S1	131.9 (3)	C6—C7—H7A	109.4
N3—C1—S1	121.7 (3)	C2—C7—H7B	109.4
N1—C2—N2	100.8 (3)	C6—C7—H7B	109.4
N1—C2—C3	112.6 (4)	H7A—C7—H7B	108.0
N2—C2—C3	109.0 (4)	N1—C8—C9	113.9 (4)
N1—C2—C7	111.6 (4)	N1—C8—H8A	108.8
N2—C2—C7	108.4 (4)	C9—C8—H8A	108.8
C3—C2—C7	113.4 (3)	N1—C8—H8B	108.8
C4—C3—C2	111.7 (4)	C9—C8—H8B	108.8
C4—C3—H3A	109.3	H8A—C8—H8B	107.7
C2—C3—H3A	109.3	C14—C9—C10	118.1 (5)
C4—C3—H3B	109.3	C14—C9—C8	121.3 (4)
C2—C3—H3B	109.3	C10—C9—C8	120.6 (4)
H3A—C3—H3B	107.9	C11—C10—C9	120.9 (5)
C5—C4—C3	111.7 (4)	C11—C10—H10	119.6
C5—C4—H4A	109.3	C9—C10—H10	119.6
C3—C4—H4A	109.3	C12—C11—C10	120.3 (5)
C5—C4—H4B	109.3	C12—C11—H11	119.9
C3—C4—H4B	109.3	C10—C11—H11	119.9
H4A—C4—H4B	107.9	C11—C12—C13	119.6 (5)
C6—C5—C4	111.5 (4)	C11—C12—H12	120.2
C6—C5—H5A	109.3	C13—C12—H12	120.2
C4—C5—H5A	109.3	C14—C13—C12	120.8 (5)
C6—C5—H5B	109.3	C14—C13—H13	119.6
C4—C5—H5B	109.3	C12—C13—H13	119.6
H5A—C5—H5B	108.0	C13—C14—C9	120.3 (5)
C5—C6—C7	112.2 (4)	C13—C14—H14	119.8
C5—C6—H6A	109.2	C9—C14—H14	119.8
C7—C6—H6A	109.2	C1—N1—C8	124.3 (4)
C5—C6—H6B	109.2	C1—N1—C2	111.0 (3)
C7—C6—H6B	109.2	C8—N1—C2	124.7 (3)
H6A—C6—H6B	107.9	N3—N2—C2	112.1 (3)
C2—C7—C6	111.4 (4)	N2—N3—C1	109.7 (4)
N1—C2—C3—C4	179.1 (4)	C8—C9—C14—C13	179.8 (5)
N2—C2—C3—C4	−69.9 (5)	N3—C1—N1—C8	−179.6 (4)
C7—C2—C3—C4	51.1 (5)	S1—C1—N1—C8	0.7 (9)
C2—C3—C4—C5	−53.4 (5)	N3—C1—N1—C2	−1.6 (6)
C3—C4—C5—C6	56.1 (5)	S1—C1—N1—C2	178.8 (4)
C4—C5—C6—C7	−55.7 (6)	C9—C8—N1—C1	−101.8 (6)
N1—C2—C7—C6	−178.9 (4)	C9—C8—N1—C2	80.4 (6)
N2—C2—C7—C6	71.0 (5)	N2—C2—N1—C1	1.5 (5)
C3—C2—C7—C6	−50.3 (5)	C3—C2—N1—C1	117.6 (5)
C5—C6—C7—C2	52.4 (6)	C7—C2—N1—C1	−113.4 (5)
N1—C8—C9—C14	54.4 (6)	N2—C2—N1—C8	179.6 (4)
N1—C8—C9—C10	−126.1 (4)	C3—C2—N1—C8	−64.4 (6)
C14—C9—C10—C11	−0.2 (7)	C7—C2—N1—C8	64.6 (6)
C8—C9—C10—C11	−179.8 (4)	N1—C2—N2—N3	−0.9 (5)
C9—C10—C11—C12	−0.3 (7)	C3—C2—N2—N3	−119.6 (5)
C10—C11—C12—C13	0.8 (8)	C7—C2—N2—N3	116.5 (5)
C11—C12—C13—C14	−0.8 (9)	C2—N2—N3—C1	0.0 (6)
C12—C13—C14—C9	0.3 (9)	N1—C1—N3—N2	1.0 (6)
C10—C9—C14—C13	0.2 (7)	S1—C1—N3—N2	−179.3 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···S1^i	0.93	2.87	3.779 (6)	166

Symmetry code: (i) −x+1, y+1/2, −z+1/2.