In the crystal structure of the title compound, C
10H
18N
2S, dimers are formed by N—H
S hydrogen bonding. These dimers are located around centers of inversion.
Supporting information
CCDC reference: 255938
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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-1
H-imidazole-2(3
H)-thione
top
Crystal data top
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) Å3 | Prism, yellow |
Z = 4 | 0.40 × 0.30 × 0.17 mm |
Data collection top
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 top
Refinement on F2 | H atoms treated by a mixture of independent and constrained refinement |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.0847P)2] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.061 | (Δ/σ)max < 0.001 |
wR(F2) = 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 top
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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···S1i | 0.79 | 2.61 | 3.394 (3) | 179 |
Symmetry code: (i) −x+2, −y, −z+2. |