4-tert-Butyl-1-iso­propyl-1H-imidazole-2(3H)-thione

In the crystal structure of the title compound, C₁₀H₁₈N₂S, dimers are formed by N—H...S hydrogen bonding. These dimers are located around centers of inversion.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.061
• wR factor = 0.197
• Data-to-parameter ratio = 23.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.10 Ratio
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors  for         C8
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C10 H18 N2 S

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

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

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Computing details

Data collection: COLLECT (Nonius, 1999); cell refinement: DENZO–SMN (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: WinGX (Farrugia, 1999).

4-tert-Butyl-1-isopropyl-1H-imidazole-2(3H)-thione

Crystal data

C10H18N2S	F(000) = 432
Mr = 198.32	Dx = 1.127 Mg m^−3
Monoclinic, P21/c	Melting point: 548 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 10.051 (2) Å	Cell parameters from 3850 reflections
b = 10.176 (2) Å	θ = 1.0–28.3°
c = 11.762 (2) Å	µ = 0.24 mm^−1
β = 103.76 (2)°	T = 293 K
V = 1168.5 (4) Å^3	Prism, yellow
Z = 4	0.40 × 0.30 × 0.17 mm

Data collection

Nonius KappaCCD area-detector diffractometer	2843 independent reflections
Radiation source: fine-focus sealed tube	1468 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.062
ω scans	θmax = 28.3°, θmin = 2.1°
Absorption correction: multi-scan (SORTAV; Blessing, 1995, 1997)	h = −13→8
Tmin = 0.919, Tmax = 0.953	k = −12→13
6718 measured reflections	l = −13→15

Refinement

Refinement on F^2	H atoms treated by a mixture of independent and constrained refinement
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + (0.0847P)^2] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.061	(Δ/σ)max < 0.001
wR(F^2) = 0.197	Δρmax = 0.44 e Å^−3
S = 1.06	Δρmin = −0.42 e Å^−3
2843 reflections	Extinction correction: SHELXL97
122 parameters	Extinction coefficient: 0.138 (8)
0 restraints

Special details

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.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
S1	0.76838 (8)	0.03727 (10)	0.95235 (6)	0.0457 (3)
N1	0.9670 (2)	0.0798 (2)	1.15124 (19)	0.0323 (6)
N2	0.7636 (2)	0.1071 (2)	1.17576 (19)	0.0338 (6)
C1	0.9839 (3)	0.1172 (3)	1.2673 (2)	0.0300 (7)
C2	0.8563 (3)	0.1344 (3)	1.2812 (2)	0.0373 (8)
C3	0.8341 (3)	0.0740 (3)	1.0955 (2)	0.0316 (7)
C4	1.1225 (3)	0.1339 (3)	1.3498 (2)	0.0374 (8)
C5	1.2052 (3)	0.2350 (4)	1.2989 (3)	0.0537 (10)
C6	1.1972 (4)	0.0024 (4)	1.3661 (3)	0.0568 (10)
C7	1.1031 (4)	0.1814 (4)	1.4676 (3)	0.0564 (10)
C8	0.6132 (3)	0.1048 (3)	1.1555 (3)	0.0395 (8)
C9	0.5716 (4)	0.0588 (5)	1.2642 (3)	0.0824 (15)
H9A	0.6201	−0.0204	1.2925	0.108 (7)*
H9B	0.4748	0.0421	1.2457	0.108 (7)*
H9C	0.5934	0.1256	1.3234	0.108 (7)*
C10	0.5535 (4)	0.2358 (4)	1.1136 (4)	0.0926 (16)
H10A	0.5748	0.2979	1.1767	0.108 (7)*
H10B	0.4559	0.2279	1.0866	0.108 (7)*
H10C	0.5914	0.2656	1.0505	0.108 (7)*
H1	1.0291	0.054	1.1278	0.039*
H2	0.8298	0.166	1.3436	0.044*
H5A	1.228	0.2016	1.2271	0.072*
H5B	1.2958	0.2482	1.3545	0.068*
H5C	1.1591	0.3166	1.288	0.081*
H6A	1.2096	−0.0336	1.2951	0.079*
H6B	1.1539	−0.0635	1.3964	0.077*
H6C	1.2819	0.0153	1.4211	0.063*
H7A	1.0517	0.1166	1.5047	0.064*
H7B	1.0565	0.2668	1.4579	0.062*
H7C	1.1884	0.1983	1.521	0.075*
H8	0.5873	0.0447	1.0983	0.038*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0339 (5)	0.0708 (7)	0.0304 (5)	0.0003 (4)	0.0037 (4)	−0.0098 (4)
N1	0.0244 (14)	0.0440 (16)	0.0299 (13)	0.0011 (11)	0.0093 (10)	−0.0064 (11)
N2	0.0234 (14)	0.0440 (16)	0.0344 (14)	−0.0009 (12)	0.0078 (11)	−0.0089 (12)
C1	0.0295 (17)	0.0357 (17)	0.0249 (14)	0.0000 (13)	0.0069 (12)	−0.0058 (13)
C2	0.0335 (18)	0.049 (2)	0.0319 (16)	−0.0018 (15)	0.0131 (13)	−0.0129 (15)
C3	0.0272 (17)	0.0363 (18)	0.0312 (16)	−0.0023 (13)	0.0070 (13)	−0.0035 (13)
C4	0.0332 (18)	0.048 (2)	0.0298 (15)	−0.0040 (15)	0.0055 (13)	−0.0078 (15)
C5	0.041 (2)	0.072 (3)	0.0472 (19)	−0.0197 (19)	0.0096 (16)	−0.0085 (19)
C6	0.052 (2)	0.073 (3)	0.0409 (19)	0.0096 (19)	0.0006 (17)	0.0004 (18)
C7	0.045 (2)	0.085 (3)	0.0382 (17)	−0.010 (2)	0.0082 (15)	−0.0171 (19)
C8	0.0241 (17)	0.050 (2)	0.0449 (18)	−0.0042 (15)	0.0082 (14)	−0.0091 (16)
C9	0.036 (2)	0.149 (5)	0.066 (3)	−0.018 (3)	0.019 (2)	0.008 (3)
C10	0.031 (2)	0.077 (3)	0.166 (5)	0.018 (2)	0.016 (3)	0.024 (3)

Geometric parameters (Å, º)

S1—C3	1.697 (3)	C6—H6A	0.9469
N1—C3	1.342 (4)	C6—H6B	0.9169
N1—C1	1.388 (3)	C6—H6C	0.9472
N1—H1	0.786	C7—H7A	0.9996
N2—C3	1.351 (3)	C7—H7B	0.9814
N2—C2	1.391 (3)	C7—H7C	0.9502
N2—C8	1.473 (4)	C8—C10	1.496 (5)
C1—C2	1.342 (4)	C8—C9	1.511 (5)
C1—C4	1.506 (4)	C8—H8	0.9
C2—H2	0.8978	C9—H9A	0.96
C4—C7	1.523 (4)	C9—H9B	0.96
C4—C6	1.524 (5)	C9—H9C	0.96
C4—C5	1.531 (4)	C10—H10A	0.96
C5—H5A	0.9874	C10—H10B	0.96
C5—H5B	0.9959	C10—H10C	0.96
C5—H5C	0.9444
C3—N1—C1	111.6 (2)	H6A—C6—H6B	103.4
C3—N1—H1	126.5	C4—C6—H6C	107.5
C1—N1—H1	121.1	H6A—C6—H6C	111.7
C3—N2—C2	108.8 (2)	H6B—C6—H6C	105.6
C3—N2—C8	124.8 (2)	C4—C7—H7A	112.3
C2—N2—C8	126.3 (2)	C4—C7—H7B	109.6
C2—C1—N1	105.0 (2)	H7A—C7—H7B	110.7
C2—C1—C4	132.1 (2)	C4—C7—H7C	111.6
N1—C1—C4	122.9 (2)	H7A—C7—H7C	108
C1—C2—N2	108.8 (2)	H7B—C7—H7C	104.3
C1—C2—H2	128.7	N2—C8—C10	110.8 (3)
N2—C2—H2	122.3	N2—C8—C9	110.3 (3)
N1—C3—N2	105.9 (2)	C10—C8—C9	112.6 (3)
N1—C3—S1	127.0 (2)	N2—C8—H8	103.6
N2—C3—S1	127.1 (2)	C10—C8—H8	109.7
C1—C4—C7	108.9 (3)	C9—C8—H8	109.4
C1—C4—C6	109.6 (3)	C8—C9—H9A	109.5
C7—C4—C6	109.2 (3)	C8—C9—H9B	109.5
C1—C4—C5	109.2 (2)	H9A—C9—H9B	109.5
C7—C4—C5	110.0 (3)	C8—C9—H9C	109.5
C6—C4—C5	110.0 (3)	H9A—C9—H9C	109.5
C4—C5—H5A	111.2	H9B—C9—H9C	109.5
C4—C5—H5B	109.3	C8—C10—H10A	109.5
H5A—C5—H5B	104.3	C8—C10—H10B	109.5
C4—C5—H5C	110.5	H10A—C10—H10B	109.5
H5A—C5—H5C	113.1	C8—C10—H10C	109.5
H5B—C5—H5C	108.2	H10A—C10—H10C	109.5
C4—C6—H6A	113.2	H10B—C10—H10C	109.5
C4—C6—H6B	115.2
C3—N1—C1—C2	0.0 (3)	C8—N2—C3—S1	6.3 (4)
C3—N1—C1—C4	−178.9 (3)	C2—C1—C4—C7	−1.1 (5)
N1—C1—C2—N2	0.4 (3)	N1—C1—C4—C7	177.4 (3)
C4—C1—C2—N2	179.2 (3)	C2—C1—C4—C6	118.3 (4)
C3—N2—C2—C1	−0.6 (4)	N1—C1—C4—C6	−63.1 (4)
C8—N2—C2—C1	175.4 (3)	C2—C1—C4—C5	−121.2 (4)
C1—N1—C3—N2	−0.3 (3)	N1—C1—C4—C5	57.4 (4)
C1—N1—C3—S1	177.9 (2)	C3—N2—C8—C10	−91.9 (4)
C2—N2—C3—N1	0.6 (3)	C2—N2—C8—C10	92.8 (4)
C8—N2—C3—N1	−175.5 (3)	C3—N2—C8—C9	142.7 (3)
C2—N2—C3—S1	−177.7 (2)	C2—N2—C8—C9	−32.6 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···S1^i	0.79	2.61	3.394 (3)	179

Symmetry code: (i) −x+2, −y, −z+2.