The title compound is composed of cyclohexane and benzene rings connected through a hydrazinecarbothioamide moiety. In the crystal, the molecules are connected by N—H

S hydrogen bonds.
Supporting information
CCDC reference: 1435681
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean
(C-C) = 0.002 Å
- R factor = 0.032
- wR factor = 0.086
- Data-to-parameter ratio = 18.8
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for S1 --C8 . 6.0 s.u.
Alert level G
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels .......... 3 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min). 1 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ... 1 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 16 Info
0 ALERT level A = Most likely a serious problem - resolve or explain
0 ALERT level B = A potentially serious problem, consider carefully
1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
4 ALERT level G = General information/check it is not something unexpected
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
3 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
1 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: APEX2 (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELX2013 (Sheldrick, 2015); molecular graphics: Mercury (Macrae et al.,
2006); software used to prepare material for publication: SHELX2013 (Sheldrick, 2015) and PLATON (Spek, 2009).
(
E)-2-[3-(
tert-Butyl)-2-hydroxybenzylidene]-
N-cyclohexylhydrazine-1-carbothioamide
top
Crystal data top
C18H27N3OS | F(000) = 720 |
Mr = 333.48 | Dx = 1.216 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 13.4168 (6) Å | Cell parameters from 9744 reflections |
b = 6.6070 (3) Å | θ = 2.4–32.8° |
c = 20.5831 (9) Å | µ = 0.19 mm−1 |
β = 93.032 (1)° | T = 100 K |
V = 1822.03 (14) Å3 | Block, colourless |
Z = 4 | 0.57 × 0.30 × 0.29 mm |
Data collection top
Bruker APEXII DUO CCD area-detector diffractometer | 4195 independent reflections |
Radiation source: fine-focus sealed tube | 3819 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.031 |
φ and ω scans | θmax = 27.5°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Bruker, 2012 | h = −17→17 |
Tmin = 0.774, Tmax = 0.879 | k = −8→8 |
39751 measured reflections | l = −25→26 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.032 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.086 | w = 1/[σ2(Fo2) + (0.0422P)2 + 0.8449P]
where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.002 |
4195 reflections | Δρmax = 0.38 e Å−3 |
223 parameters | Δρmin = −0.22 e Å−3 |
Special details top
Experimental. The following wavelength and cell were deduced by SADABS from the
direction cosines etc. They are given here for emergency use only:
CELL 0.71104 13.523 6.653 20.749 89.939 93.047 89.965 |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
S1 | 1.02419 (2) | −0.15365 (4) | 0.40715 (2) | 0.01701 (8) | |
O1 | 0.65801 (6) | 0.39888 (12) | 0.39017 (4) | 0.02153 (18) | |
N1 | 0.84612 (7) | 0.31101 (14) | 0.42569 (4) | 0.01542 (18) | |
N2 | 0.92566 (7) | 0.17823 (14) | 0.43545 (5) | 0.01565 (19) | |
N3 | 0.88665 (7) | 0.04928 (14) | 0.33416 (4) | 0.01665 (19) | |
C1 | 0.67407 (8) | 0.57899 (16) | 0.42115 (5) | 0.0155 (2) | |
C2 | 0.59978 (8) | 0.72977 (17) | 0.41452 (5) | 0.0164 (2) | |
C3 | 0.61893 (8) | 0.91139 (17) | 0.44745 (5) | 0.0189 (2) | |
H3A | 0.5707 | 1.0165 | 0.4433 | 0.023* | |
C4 | 0.70586 (8) | 0.94540 (17) | 0.48615 (5) | 0.0190 (2) | |
H4A | 0.7155 | 1.0707 | 0.5082 | 0.023* | |
C5 | 0.77763 (8) | 0.79630 (16) | 0.49220 (5) | 0.0164 (2) | |
H5A | 0.8366 | 0.8182 | 0.5189 | 0.020* | |
C6 | 0.76359 (8) | 0.61241 (16) | 0.45906 (5) | 0.0145 (2) | |
C7 | 0.84439 (8) | 0.46494 (16) | 0.46392 (5) | 0.0151 (2) | |
H7A | 0.8971 | 0.4829 | 0.4961 | 0.018* | |
C8 | 0.93944 (8) | 0.03134 (16) | 0.39073 (5) | 0.0148 (2) | |
C9 | 0.88503 (8) | −0.09682 (16) | 0.28052 (5) | 0.0145 (2) | |
H9A | 0.9545 | −0.1468 | 0.2754 | 0.017* | |
C10 | 0.81847 (8) | −0.27750 (17) | 0.29436 (5) | 0.0185 (2) | |
H10A | 0.7505 | −0.2291 | 0.3028 | 0.022* | |
H10B | 0.8454 | −0.3488 | 0.3338 | 0.022* | |
C11 | 0.81297 (9) | −0.42424 (17) | 0.23685 (6) | 0.0213 (2) | |
H11A | 0.8797 | −0.4841 | 0.2316 | 0.026* | |
H11B | 0.7663 | −0.5356 | 0.2459 | 0.026* | |
C12 | 0.77785 (9) | −0.31813 (17) | 0.17386 (6) | 0.0206 (2) | |
H12A | 0.7080 | −0.2728 | 0.1771 | 0.025* | |
H12B | 0.7798 | −0.4147 | 0.1372 | 0.025* | |
C13 | 0.84377 (9) | −0.13575 (17) | 0.16058 (5) | 0.0200 (2) | |
H13A | 0.8166 | −0.0644 | 0.1212 | 0.024* | |
H13B | 0.9119 | −0.1831 | 0.1521 | 0.024* | |
C14 | 0.84919 (8) | 0.01120 (16) | 0.21804 (5) | 0.0175 (2) | |
H14A | 0.8956 | 0.1230 | 0.2090 | 0.021* | |
H14B | 0.7824 | 0.0703 | 0.2236 | 0.021* | |
C15 | 0.50170 (8) | 0.69323 (18) | 0.37398 (6) | 0.0212 (2) | |
C16 | 0.44095 (10) | 0.5302 (2) | 0.40747 (7) | 0.0339 (3) | |
H16A | 0.4784 | 0.4028 | 0.4090 | 0.051* | |
H16B | 0.3771 | 0.5102 | 0.3829 | 0.051* | |
H16C | 0.4285 | 0.5737 | 0.4518 | 0.051* | |
C17 | 0.52133 (10) | 0.6286 (2) | 0.30399 (6) | 0.0300 (3) | |
H17A | 0.5615 | 0.7323 | 0.2835 | 0.045* | |
H17B | 0.4576 | 0.6128 | 0.2790 | 0.045* | |
H17C | 0.5574 | 0.4997 | 0.3048 | 0.045* | |
C18 | 0.43846 (10) | 0.8868 (2) | 0.36863 (6) | 0.0290 (3) | |
H18A | 0.4767 | 0.9941 | 0.3484 | 0.043* | |
H18B | 0.4211 | 0.9298 | 0.4122 | 0.043* | |
H18C | 0.3773 | 0.8600 | 0.3419 | 0.043* | |
H1N2 | 0.9483 (11) | 0.161 (2) | 0.4737 (7) | 0.020 (3)* | |
H1O1 | 0.7098 (14) | 0.330 (3) | 0.3961 (9) | 0.043 (5)* | |
H1N3 | 0.8464 (11) | 0.149 (2) | 0.3316 (7) | 0.025 (4)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.01723 (14) | 0.01842 (14) | 0.01519 (14) | 0.00573 (10) | −0.00098 (10) | −0.00137 (9) |
O1 | 0.0196 (4) | 0.0160 (4) | 0.0282 (4) | 0.0037 (3) | −0.0070 (3) | −0.0059 (3) |
N1 | 0.0151 (4) | 0.0153 (4) | 0.0158 (4) | 0.0025 (3) | 0.0001 (3) | 0.0010 (3) |
N2 | 0.0162 (4) | 0.0168 (4) | 0.0135 (4) | 0.0049 (3) | −0.0025 (3) | −0.0005 (3) |
N3 | 0.0192 (4) | 0.0151 (4) | 0.0153 (4) | 0.0045 (4) | −0.0023 (3) | −0.0021 (3) |
C1 | 0.0177 (5) | 0.0139 (5) | 0.0152 (5) | −0.0003 (4) | 0.0017 (4) | −0.0002 (4) |
C2 | 0.0156 (5) | 0.0185 (5) | 0.0152 (5) | 0.0019 (4) | 0.0023 (4) | 0.0021 (4) |
C3 | 0.0197 (5) | 0.0166 (5) | 0.0207 (5) | 0.0041 (4) | 0.0048 (4) | 0.0012 (4) |
C4 | 0.0231 (5) | 0.0148 (5) | 0.0195 (5) | −0.0004 (4) | 0.0045 (4) | −0.0025 (4) |
C5 | 0.0172 (5) | 0.0172 (5) | 0.0151 (5) | −0.0022 (4) | 0.0026 (4) | −0.0005 (4) |
C6 | 0.0161 (5) | 0.0144 (5) | 0.0132 (5) | 0.0009 (4) | 0.0026 (4) | 0.0014 (4) |
C7 | 0.0150 (5) | 0.0160 (5) | 0.0142 (5) | −0.0001 (4) | 0.0002 (4) | 0.0012 (4) |
C8 | 0.0140 (5) | 0.0146 (5) | 0.0158 (5) | −0.0007 (4) | 0.0015 (4) | −0.0002 (4) |
C9 | 0.0155 (5) | 0.0144 (5) | 0.0137 (5) | 0.0009 (4) | 0.0002 (4) | −0.0016 (4) |
C10 | 0.0205 (5) | 0.0180 (5) | 0.0170 (5) | −0.0018 (4) | 0.0006 (4) | 0.0023 (4) |
C11 | 0.0251 (6) | 0.0153 (5) | 0.0233 (6) | −0.0024 (4) | −0.0012 (4) | −0.0005 (4) |
C12 | 0.0228 (5) | 0.0203 (5) | 0.0183 (5) | −0.0030 (4) | −0.0020 (4) | −0.0033 (4) |
C13 | 0.0242 (6) | 0.0218 (5) | 0.0140 (5) | −0.0031 (4) | 0.0006 (4) | −0.0012 (4) |
C14 | 0.0215 (5) | 0.0153 (5) | 0.0156 (5) | −0.0016 (4) | −0.0005 (4) | 0.0010 (4) |
C15 | 0.0168 (5) | 0.0252 (6) | 0.0211 (6) | 0.0049 (4) | −0.0022 (4) | −0.0007 (4) |
C16 | 0.0194 (6) | 0.0392 (7) | 0.0422 (8) | −0.0066 (5) | −0.0058 (5) | 0.0052 (6) |
C17 | 0.0263 (6) | 0.0391 (7) | 0.0237 (6) | 0.0126 (5) | −0.0071 (5) | −0.0079 (5) |
C18 | 0.0237 (6) | 0.0352 (7) | 0.0274 (6) | 0.0138 (5) | −0.0035 (5) | −0.0036 (5) |
Geometric parameters (Å, º) top
S1—C8 | 1.6912 (11) | C10—H10A | 0.9900 |
O1—C1 | 1.3619 (13) | C10—H10B | 0.9900 |
O1—H1O1 | 0.836 (19) | C11—C12 | 1.5264 (16) |
N1—C7 | 1.2867 (14) | C11—H11A | 0.9900 |
N1—N2 | 1.3879 (12) | C11—H11B | 0.9900 |
N2—C8 | 1.3571 (14) | C12—C13 | 1.5279 (16) |
N2—H1N2 | 0.836 (15) | C12—H12A | 0.9900 |
N3—C8 | 1.3357 (14) | C12—H12B | 0.9900 |
N3—C9 | 1.4659 (13) | C13—C14 | 1.5290 (15) |
N3—H1N3 | 0.854 (16) | C13—H13A | 0.9900 |
C1—C2 | 1.4107 (15) | C13—H13B | 0.9900 |
C1—C6 | 1.4145 (15) | C14—H14A | 0.9900 |
C2—C3 | 1.3953 (16) | C14—H14B | 0.9900 |
C2—C15 | 1.5394 (15) | C15—C18 | 1.5354 (16) |
C3—C4 | 1.3953 (16) | C15—C16 | 1.5359 (18) |
C3—H3A | 0.9500 | C15—C17 | 1.5384 (17) |
C4—C5 | 1.3786 (15) | C16—H16A | 0.9800 |
C4—H4A | 0.9500 | C16—H16B | 0.9800 |
C5—C6 | 1.4012 (15) | C16—H16C | 0.9800 |
C5—H5A | 0.9500 | C17—H17A | 0.9800 |
C6—C7 | 1.4571 (14) | C17—H17B | 0.9800 |
C7—H7A | 0.9500 | C17—H17C | 0.9800 |
C9—C14 | 1.5260 (14) | C18—H18A | 0.9800 |
C9—C10 | 1.5265 (15) | C18—H18B | 0.9800 |
C9—H9A | 1.0000 | C18—H18C | 0.9800 |
C10—C11 | 1.5288 (16) | | |
| | | |
C1—O1—H1O1 | 107.5 (12) | C10—C11—H11A | 109.3 |
C7—N1—N2 | 116.72 (9) | C12—C11—H11B | 109.3 |
C8—N2—N1 | 119.02 (9) | C10—C11—H11B | 109.3 |
C8—N2—H1N2 | 119.2 (10) | H11A—C11—H11B | 108.0 |
N1—N2—H1N2 | 117.3 (10) | C11—C12—C13 | 111.02 (9) |
C8—N3—C9 | 125.75 (9) | C11—C12—H12A | 109.4 |
C8—N3—H1N3 | 115.2 (10) | C13—C12—H12A | 109.4 |
C9—N3—H1N3 | 118.7 (10) | C11—C12—H12B | 109.4 |
O1—C1—C2 | 118.57 (9) | C13—C12—H12B | 109.4 |
O1—C1—C6 | 120.22 (9) | H12A—C12—H12B | 108.0 |
C2—C1—C6 | 121.21 (10) | C12—C13—C14 | 111.51 (9) |
C3—C2—C1 | 116.69 (10) | C12—C13—H13A | 109.3 |
C3—C2—C15 | 121.90 (10) | C14—C13—H13A | 109.3 |
C1—C2—C15 | 121.40 (10) | C12—C13—H13B | 109.3 |
C2—C3—C4 | 122.87 (10) | C14—C13—H13B | 109.3 |
C2—C3—H3A | 118.6 | H13A—C13—H13B | 108.0 |
C4—C3—H3A | 118.6 | C9—C14—C13 | 110.78 (9) |
C5—C4—C3 | 119.68 (10) | C9—C14—H14A | 109.5 |
C5—C4—H4A | 120.2 | C13—C14—H14A | 109.5 |
C3—C4—H4A | 120.2 | C9—C14—H14B | 109.5 |
C4—C5—C6 | 120.02 (10) | C13—C14—H14B | 109.5 |
C4—C5—H5A | 120.0 | H14A—C14—H14B | 108.1 |
C6—C5—H5A | 120.0 | C18—C15—C16 | 108.16 (10) |
C5—C6—C1 | 119.49 (10) | C18—C15—C17 | 106.58 (10) |
C5—C6—C7 | 117.78 (9) | C16—C15—C17 | 110.30 (11) |
C1—C6—C7 | 122.71 (10) | C18—C15—C2 | 111.19 (10) |
N1—C7—C6 | 121.60 (9) | C16—C15—C2 | 108.99 (9) |
N1—C7—H7A | 119.2 | C17—C15—C2 | 111.55 (9) |
C6—C7—H7A | 119.2 | C15—C16—H16A | 109.5 |
N3—C8—N2 | 116.29 (9) | C15—C16—H16B | 109.5 |
N3—C8—S1 | 123.94 (8) | H16A—C16—H16B | 109.5 |
N2—C8—S1 | 119.70 (8) | C15—C16—H16C | 109.5 |
N3—C9—C14 | 108.55 (9) | H16A—C16—H16C | 109.5 |
N3—C9—C10 | 111.09 (9) | H16B—C16—H16C | 109.5 |
C14—C9—C10 | 111.20 (9) | C15—C17—H17A | 109.5 |
N3—C9—H9A | 108.6 | C15—C17—H17B | 109.5 |
C14—C9—H9A | 108.6 | H17A—C17—H17B | 109.5 |
C10—C9—H9A | 108.6 | C15—C17—H17C | 109.5 |
C9—C10—C11 | 110.87 (9) | H17A—C17—H17C | 109.5 |
C9—C10—H10A | 109.5 | H17B—C17—H17C | 109.5 |
C11—C10—H10A | 109.5 | C15—C18—H18A | 109.5 |
C9—C10—H10B | 109.5 | C15—C18—H18B | 109.5 |
C11—C10—H10B | 109.5 | H18A—C18—H18B | 109.5 |
H10A—C10—H10B | 108.1 | C15—C18—H18C | 109.5 |
C12—C11—C10 | 111.50 (9) | H18A—C18—H18C | 109.5 |
C12—C11—H11A | 109.3 | H18B—C18—H18C | 109.5 |
| | | |
C7—N1—N2—C8 | −170.08 (10) | C9—N3—C8—S1 | 6.94 (16) |
O1—C1—C2—C3 | 179.54 (10) | N1—N2—C8—N3 | 12.50 (15) |
C6—C1—C2—C3 | −0.44 (15) | N1—N2—C8—S1 | −170.46 (8) |
O1—C1—C2—C15 | 0.70 (15) | C8—N3—C9—C14 | −159.15 (10) |
C6—C1—C2—C15 | −179.27 (10) | C8—N3—C9—C10 | 78.28 (13) |
C1—C2—C3—C4 | −0.95 (16) | N3—C9—C10—C11 | 177.21 (9) |
C15—C2—C3—C4 | 177.88 (10) | C14—C9—C10—C11 | 56.19 (12) |
C2—C3—C4—C5 | 0.87 (17) | C9—C10—C11—C12 | −55.62 (12) |
C3—C4—C5—C6 | 0.64 (16) | C10—C11—C12—C13 | 55.03 (13) |
C4—C5—C6—C1 | −1.98 (16) | C11—C12—C13—C14 | −55.10 (13) |
C4—C5—C6—C7 | 176.29 (10) | N3—C9—C14—C13 | −178.71 (9) |
O1—C1—C6—C5 | −178.09 (9) | C10—C9—C14—C13 | −56.20 (12) |
C2—C1—C6—C5 | 1.89 (16) | C12—C13—C14—C9 | 55.70 (12) |
O1—C1—C6—C7 | 3.74 (16) | C3—C2—C15—C18 | 7.08 (15) |
C2—C1—C6—C7 | −176.29 (10) | C1—C2—C15—C18 | −174.15 (10) |
N2—N1—C7—C6 | −178.82 (9) | C3—C2—C15—C16 | −112.06 (12) |
C5—C6—C7—N1 | −166.41 (10) | C1—C2—C15—C16 | 66.72 (14) |
C1—C6—C7—N1 | 11.80 (16) | C3—C2—C15—C17 | 125.90 (12) |
C9—N3—C8—N2 | −176.16 (10) | C1—C2—C15—C17 | −55.32 (14) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O1···N1 | 0.834 (19) | 1.901 (19) | 2.6545 (12) | 149.6 (19) |
C16—H16A···O1 | 0.98 | 2.46 | 3.0774 (16) | 121 |
C17—H17C···O1 | 0.98 | 2.26 | 2.9101 (15) | 123 |
N2—H1N2···S1i | 0.833 (14) | 2.459 (14) | 3.2779 (11) | 165.6 (13) |
Symmetry code: (i) −x+2, −y, −z+1. |
Selected dihedral and torsion angles (°) topDihedral is the dihedral angle between the mean planes of
the benzylidene ring and the hydrazinecarbothioamide moiety.
τ5 is the C8—N3—C9—C10 torsion angle. |
Compound | Dihedral | τ5 |
Title compound | 31.13 (5) | 78.32 |
BEVNAR | 28.50 | 94.47 |
LAQCIR | 16.64 | 86.22 |
NALKOD | 22.00, 36.40 | 79.01, 79.19 |
OBOLOJ | 6.92 | 83.70 |
XOYKAZ | 12.72 | 85.82 |
BEFZIY | 4.70 | 83.42 |