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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989018013129/ld2145sup1.cif
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989018013129/ld2145Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989018013129/ld2145Isup3.cml
Supplementary material

CCDC reference: 1435681

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](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

Computing details top

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
C18H27N3OSF(000) = 720
Mr = 333.48Dx = 1.216 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 13.4168 (6) ÅCell parameters from 9744 reflections
b = 6.6070 (3) Åθ = 2.4–32.8°
c = 20.5831 (9) ŵ = 0.19 mm1
β = 93.032 (1)°T = 100 K
V = 1822.03 (14) Å3Block, colourless
Z = 40.57 × 0.30 × 0.29 mm
Data collection top
Bruker APEXII DUO CCD area-detector
diffractometer
4195 independent reflections
Radiation source: fine-focus sealed tube3819 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
φ and ω scansθmax = 27.5°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2012
h = 1717
Tmin = 0.774, Tmax = 0.879k = 88
39751 measured reflectionsl = 2526
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.032H 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 reflectionsΔρmax = 0.38 e Å3
223 parametersΔρmin = 0.22 e Å3
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
xyzUiso*/Ueq
S11.02419 (2)0.15365 (4)0.40715 (2)0.01701 (8)
O10.65801 (6)0.39888 (12)0.39017 (4)0.02153 (18)
N10.84612 (7)0.31101 (14)0.42569 (4)0.01542 (18)
N20.92566 (7)0.17823 (14)0.43545 (5)0.01565 (19)
N30.88665 (7)0.04928 (14)0.33416 (4)0.01665 (19)
C10.67407 (8)0.57899 (16)0.42115 (5)0.0155 (2)
C20.59978 (8)0.72977 (17)0.41452 (5)0.0164 (2)
C30.61893 (8)0.91139 (17)0.44745 (5)0.0189 (2)
H3A0.57071.01650.44330.023*
C40.70586 (8)0.94540 (17)0.48615 (5)0.0190 (2)
H4A0.71551.07070.50820.023*
C50.77763 (8)0.79630 (16)0.49220 (5)0.0164 (2)
H5A0.83660.81820.51890.020*
C60.76359 (8)0.61241 (16)0.45906 (5)0.0145 (2)
C70.84439 (8)0.46494 (16)0.46392 (5)0.0151 (2)
H7A0.89710.48290.49610.018*
C80.93944 (8)0.03134 (16)0.39073 (5)0.0148 (2)
C90.88503 (8)0.09682 (16)0.28052 (5)0.0145 (2)
H9A0.95450.14680.27540.017*
C100.81847 (8)0.27750 (17)0.29436 (5)0.0185 (2)
H10A0.75050.22910.30280.022*
H10B0.84540.34880.33380.022*
C110.81297 (9)0.42424 (17)0.23685 (6)0.0213 (2)
H11A0.87970.48410.23160.026*
H11B0.76630.53560.24590.026*
C120.77785 (9)0.31813 (17)0.17386 (6)0.0206 (2)
H12A0.70800.27280.17710.025*
H12B0.77980.41470.13720.025*
C130.84377 (9)0.13575 (17)0.16058 (5)0.0200 (2)
H13A0.81660.06440.12120.024*
H13B0.91190.18310.15210.024*
C140.84919 (8)0.01120 (16)0.21804 (5)0.0175 (2)
H14A0.89560.12300.20900.021*
H14B0.78240.07030.22360.021*
C150.50170 (8)0.69323 (18)0.37398 (6)0.0212 (2)
C160.44095 (10)0.5302 (2)0.40747 (7)0.0339 (3)
H16A0.47840.40280.40900.051*
H16B0.37710.51020.38290.051*
H16C0.42850.57370.45180.051*
C170.52133 (10)0.6286 (2)0.30399 (6)0.0300 (3)
H17A0.56150.73230.28350.045*
H17B0.45760.61280.27900.045*
H17C0.55740.49970.30480.045*
C180.43846 (10)0.8868 (2)0.36863 (6)0.0290 (3)
H18A0.47670.99410.34840.043*
H18B0.42110.92980.41220.043*
H18C0.37730.86000.34190.043*
H1N20.9483 (11)0.161 (2)0.4737 (7)0.020 (3)*
H1O10.7098 (14)0.330 (3)0.3961 (9)0.043 (5)*
H1N30.8464 (11)0.149 (2)0.3316 (7)0.025 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.01723 (14)0.01842 (14)0.01519 (14)0.00573 (10)0.00098 (10)0.00137 (9)
O10.0196 (4)0.0160 (4)0.0282 (4)0.0037 (3)0.0070 (3)0.0059 (3)
N10.0151 (4)0.0153 (4)0.0158 (4)0.0025 (3)0.0001 (3)0.0010 (3)
N20.0162 (4)0.0168 (4)0.0135 (4)0.0049 (3)0.0025 (3)0.0005 (3)
N30.0192 (4)0.0151 (4)0.0153 (4)0.0045 (4)0.0023 (3)0.0021 (3)
C10.0177 (5)0.0139 (5)0.0152 (5)0.0003 (4)0.0017 (4)0.0002 (4)
C20.0156 (5)0.0185 (5)0.0152 (5)0.0019 (4)0.0023 (4)0.0021 (4)
C30.0197 (5)0.0166 (5)0.0207 (5)0.0041 (4)0.0048 (4)0.0012 (4)
C40.0231 (5)0.0148 (5)0.0195 (5)0.0004 (4)0.0045 (4)0.0025 (4)
C50.0172 (5)0.0172 (5)0.0151 (5)0.0022 (4)0.0026 (4)0.0005 (4)
C60.0161 (5)0.0144 (5)0.0132 (5)0.0009 (4)0.0026 (4)0.0014 (4)
C70.0150 (5)0.0160 (5)0.0142 (5)0.0001 (4)0.0002 (4)0.0012 (4)
C80.0140 (5)0.0146 (5)0.0158 (5)0.0007 (4)0.0015 (4)0.0002 (4)
C90.0155 (5)0.0144 (5)0.0137 (5)0.0009 (4)0.0002 (4)0.0016 (4)
C100.0205 (5)0.0180 (5)0.0170 (5)0.0018 (4)0.0006 (4)0.0023 (4)
C110.0251 (6)0.0153 (5)0.0233 (6)0.0024 (4)0.0012 (4)0.0005 (4)
C120.0228 (5)0.0203 (5)0.0183 (5)0.0030 (4)0.0020 (4)0.0033 (4)
C130.0242 (6)0.0218 (5)0.0140 (5)0.0031 (4)0.0006 (4)0.0012 (4)
C140.0215 (5)0.0153 (5)0.0156 (5)0.0016 (4)0.0005 (4)0.0010 (4)
C150.0168 (5)0.0252 (6)0.0211 (6)0.0049 (4)0.0022 (4)0.0007 (4)
C160.0194 (6)0.0392 (7)0.0422 (8)0.0066 (5)0.0058 (5)0.0052 (6)
C170.0263 (6)0.0391 (7)0.0237 (6)0.0126 (5)0.0071 (5)0.0079 (5)
C180.0237 (6)0.0352 (7)0.0274 (6)0.0138 (5)0.0035 (5)0.0036 (5)
Geometric parameters (Å, º) top
S1—C81.6912 (11)C10—H10A0.9900
O1—C11.3619 (13)C10—H10B0.9900
O1—H1O10.836 (19)C11—C121.5264 (16)
N1—C71.2867 (14)C11—H11A0.9900
N1—N21.3879 (12)C11—H11B0.9900
N2—C81.3571 (14)C12—C131.5279 (16)
N2—H1N20.836 (15)C12—H12A0.9900
N3—C81.3357 (14)C12—H12B0.9900
N3—C91.4659 (13)C13—C141.5290 (15)
N3—H1N30.854 (16)C13—H13A0.9900
C1—C21.4107 (15)C13—H13B0.9900
C1—C61.4145 (15)C14—H14A0.9900
C2—C31.3953 (16)C14—H14B0.9900
C2—C151.5394 (15)C15—C181.5354 (16)
C3—C41.3953 (16)C15—C161.5359 (18)
C3—H3A0.9500C15—C171.5384 (17)
C4—C51.3786 (15)C16—H16A0.9800
C4—H4A0.9500C16—H16B0.9800
C5—C61.4012 (15)C16—H16C0.9800
C5—H5A0.9500C17—H17A0.9800
C6—C71.4571 (14)C17—H17B0.9800
C7—H7A0.9500C17—H17C0.9800
C9—C141.5260 (14)C18—H18A0.9800
C9—C101.5265 (15)C18—H18B0.9800
C9—H9A1.0000C18—H18C0.9800
C10—C111.5288 (16)
C1—O1—H1O1107.5 (12)C10—C11—H11A109.3
C7—N1—N2116.72 (9)C12—C11—H11B109.3
C8—N2—N1119.02 (9)C10—C11—H11B109.3
C8—N2—H1N2119.2 (10)H11A—C11—H11B108.0
N1—N2—H1N2117.3 (10)C11—C12—C13111.02 (9)
C8—N3—C9125.75 (9)C11—C12—H12A109.4
C8—N3—H1N3115.2 (10)C13—C12—H12A109.4
C9—N3—H1N3118.7 (10)C11—C12—H12B109.4
O1—C1—C2118.57 (9)C13—C12—H12B109.4
O1—C1—C6120.22 (9)H12A—C12—H12B108.0
C2—C1—C6121.21 (10)C12—C13—C14111.51 (9)
C3—C2—C1116.69 (10)C12—C13—H13A109.3
C3—C2—C15121.90 (10)C14—C13—H13A109.3
C1—C2—C15121.40 (10)C12—C13—H13B109.3
C2—C3—C4122.87 (10)C14—C13—H13B109.3
C2—C3—H3A118.6H13A—C13—H13B108.0
C4—C3—H3A118.6C9—C14—C13110.78 (9)
C5—C4—C3119.68 (10)C9—C14—H14A109.5
C5—C4—H4A120.2C13—C14—H14A109.5
C3—C4—H4A120.2C9—C14—H14B109.5
C4—C5—C6120.02 (10)C13—C14—H14B109.5
C4—C5—H5A120.0H14A—C14—H14B108.1
C6—C5—H5A120.0C18—C15—C16108.16 (10)
C5—C6—C1119.49 (10)C18—C15—C17106.58 (10)
C5—C6—C7117.78 (9)C16—C15—C17110.30 (11)
C1—C6—C7122.71 (10)C18—C15—C2111.19 (10)
N1—C7—C6121.60 (9)C16—C15—C2108.99 (9)
N1—C7—H7A119.2C17—C15—C2111.55 (9)
C6—C7—H7A119.2C15—C16—H16A109.5
N3—C8—N2116.29 (9)C15—C16—H16B109.5
N3—C8—S1123.94 (8)H16A—C16—H16B109.5
N2—C8—S1119.70 (8)C15—C16—H16C109.5
N3—C9—C14108.55 (9)H16A—C16—H16C109.5
N3—C9—C10111.09 (9)H16B—C16—H16C109.5
C14—C9—C10111.20 (9)C15—C17—H17A109.5
N3—C9—H9A108.6C15—C17—H17B109.5
C14—C9—H9A108.6H17A—C17—H17B109.5
C10—C9—H9A108.6C15—C17—H17C109.5
C9—C10—C11110.87 (9)H17A—C17—H17C109.5
C9—C10—H10A109.5H17B—C17—H17C109.5
C11—C10—H10A109.5C15—C18—H18A109.5
C9—C10—H10B109.5C15—C18—H18B109.5
C11—C10—H10B109.5H18A—C18—H18B109.5
H10A—C10—H10B108.1C15—C18—H18C109.5
C12—C11—C10111.50 (9)H18A—C18—H18C109.5
C12—C11—H11A109.3H18B—C18—H18C109.5
C7—N1—N2—C8170.08 (10)C9—N3—C8—S16.94 (16)
O1—C1—C2—C3179.54 (10)N1—N2—C8—N312.50 (15)
C6—C1—C2—C30.44 (15)N1—N2—C8—S1170.46 (8)
O1—C1—C2—C150.70 (15)C8—N3—C9—C14159.15 (10)
C6—C1—C2—C15179.27 (10)C8—N3—C9—C1078.28 (13)
C1—C2—C3—C40.95 (16)N3—C9—C10—C11177.21 (9)
C15—C2—C3—C4177.88 (10)C14—C9—C10—C1156.19 (12)
C2—C3—C4—C50.87 (17)C9—C10—C11—C1255.62 (12)
C3—C4—C5—C60.64 (16)C10—C11—C12—C1355.03 (13)
C4—C5—C6—C11.98 (16)C11—C12—C13—C1455.10 (13)
C4—C5—C6—C7176.29 (10)N3—C9—C14—C13178.71 (9)
O1—C1—C6—C5178.09 (9)C10—C9—C14—C1356.20 (12)
C2—C1—C6—C51.89 (16)C12—C13—C14—C955.70 (12)
O1—C1—C6—C73.74 (16)C3—C2—C15—C187.08 (15)
C2—C1—C6—C7176.29 (10)C1—C2—C15—C18174.15 (10)
N2—N1—C7—C6178.82 (9)C3—C2—C15—C16112.06 (12)
C5—C6—C7—N1166.41 (10)C1—C2—C15—C1666.72 (14)
C1—C6—C7—N111.80 (16)C3—C2—C15—C17125.90 (12)
C9—N3—C8—N2176.16 (10)C1—C2—C15—C1755.32 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1O1···N10.834 (19)1.901 (19)2.6545 (12)149.6 (19)
C16—H16A···O10.982.463.0774 (16)121
C17—H17C···O10.982.262.9101 (15)123
N2—H1N2···S1i0.833 (14)2.459 (14)3.2779 (11)165.6 (13)
Symmetry code: (i) x+2, y, z+1.
Selected dihedral and torsion angles (°) top
Dihedral 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.
CompoundDihedralτ5
Title compound31.13 (5)78.32
BEVNAR28.5094.47
LAQCIR16.6486.22
NALKOD22.00, 36.4079.01, 79.19
OBOLOJ6.9283.70
XOYKAZ12.7285.82
BEFZIY4.7083.42
 

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