(E)-2-(5-Chloro-2-hy­droxy­benzyl­idene)-N-cyclo­hexyl­hydrazine-1-carbo­thio­amide

In the title compound, C₁₄H₁₈ClN₃OS, the phenol ring is almost coplanar with the hydrazinecarbo­thio­amide moiety, making a dihedral angle of 6.92 (8)°. The cyclo­hexane ring has a chair conformation and the conformation about the C=N bond is E. In the crystal, mol­ecules are linked by N—H...O and O—H...S hydrogen bonds, forming inversion dimers with an R₂²(14) ring motif flanked by two R₂²(6) ring motifs. The dimers are linked by short Cl...Cl inter­actions, forming layers parallel to the ab plane.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.053
• wR factor = 0.130
• Data-to-parameter ratio = 25.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT417_ALERT_2_C Short Inter D-H..H-D       H1N2   ..  H1O1    ..       2.13 Ang.
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      6.739 Check
PLAT934_ALERT_3_C Number of (Iobs-Icalc)/SigmaW > 10 Outliers ....          1 Check

Alert level G
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)     0.0009 Degree
PLAT434_ALERT_2_G Short Inter HL..HL Contact Cl1    ..  Cl1     ..       3.38 Ang.
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          3 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         52 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         11 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   5 ALERT level G = General information/check it is not something unexpected

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

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Computing details

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS2014 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015), PLATON (Spek, 2009), and publCIF (Westrip, 2010).

(E)-2-(5-Chloro-2-hydroxybenzylidene)-N-cyclohexylhydrazine-1-carbothioamide

Crystal data

C14H18ClN3OS	Z = 2
Mr = 311.82	F(000) = 328
Triclinic, P1	Dx = 1.369 Mg m^−3
a = 5.9923 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.0704 (2) Å	Cell parameters from 9894 reflections
c = 12.1128 (3) Å	θ = 2.2–31.1°
α = 107.9815 (9)°	µ = 0.39 mm^−1
β = 91.3414 (9)°	T = 294 K
γ = 97.2061 (9)°	Block, colourless
V = 756.60 (3) Å^3	0.38 × 0.30 × 0.17 mm

Data collection

Bruker APEXII CCD diffractometer	4127 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.020
φ and ω scans	θmax = 31.1°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −8→8
Tmin = 0.786, Tmax = 0.828	k = −16→15
30649 measured reflections	l = −17→17
4824 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.053	Hydrogen site location: mixed
wR(F^2) = 0.130	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	w = 1/[σ^2(Fo^2) + (0.0404P)^2 + 0.4563P] where P = (Fo^2 + 2Fc^2)/3
4824 reflections	(Δ/σ)max = 0.001
193 parameters	Δρmax = 0.39 e Å^−3
0 restraints	Δρmin = −0.22 e Å^−3

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.

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

	x	y	z	Uiso*/Ueq
Cl1	1.32841 (10)	0.60273 (5)	0.57378 (5)	0.05951 (16)
S1	0.06031 (8)	0.65852 (5)	0.18924 (5)	0.04950 (15)
O1	0.8649 (3)	1.05436 (14)	0.65422 (15)	0.0584 (4)
N1	0.6106 (2)	0.73735 (13)	0.39402 (13)	0.0377 (3)
N2	0.4169 (3)	0.74695 (15)	0.33704 (14)	0.0439 (4)
N3	0.4146 (3)	0.54276 (14)	0.21687 (14)	0.0418 (3)
C1	1.0026 (3)	0.73197 (15)	0.53033 (15)	0.0380 (3)
H1A	0.9441	0.6553	0.4741	0.046*
C2	1.1981 (3)	0.73946 (17)	0.59555 (16)	0.0407 (4)
C3	1.2937 (3)	0.85327 (19)	0.67687 (17)	0.0454 (4)
H3A	1.4293	0.8577	0.7179	0.054*
C4	1.1854 (3)	0.96030 (18)	0.69645 (16)	0.0445 (4)
H4A	1.2482	1.0373	0.7510	0.053*
C5	0.9830 (3)	0.95343 (16)	0.63494 (15)	0.0391 (4)
C6	0.8924 (3)	0.83966 (15)	0.54870 (14)	0.0344 (3)
C7	0.6881 (3)	0.83640 (15)	0.47930 (15)	0.0374 (3)
H7A	0.6127	0.9078	0.4974	0.045*
C8	0.3097 (3)	0.64537 (16)	0.24909 (15)	0.0367 (3)
C9	0.3252 (3)	0.42105 (15)	0.12876 (15)	0.0374 (3)
H9A	0.2394	0.4398	0.0676	0.045*
C10	0.1685 (4)	0.3369 (2)	0.17991 (18)	0.0513 (5)
H10A	0.0424	0.3807	0.2111	0.062*
H10B	0.2486	0.3203	0.2431	0.062*
C11	0.0815 (4)	0.2101 (2)	0.0864 (2)	0.0643 (6)
H11A	−0.0138	0.1556	0.1206	0.077*
H11B	−0.0091	0.2265	0.0265	0.077*
C12	0.2755 (5)	0.14128 (19)	0.0318 (2)	0.0639 (6)
H12A	0.3584	0.1181	0.0902	0.077*
H12B	0.2162	0.0631	−0.0295	0.077*
C13	0.4329 (4)	0.22641 (19)	−0.01810 (19)	0.0550 (5)
H13A	0.3534	0.2429	−0.0815	0.066*
H13B	0.5591	0.1826	−0.0491	0.066*
C14	0.5210 (3)	0.35397 (18)	0.07495 (18)	0.0477 (4)
H14A	0.6126	0.3384	0.1349	0.057*
H14B	0.6149	0.4085	0.0402	0.057*
H1N3	0.535 (4)	0.548 (2)	0.253 (2)	0.051 (6)*
H1N2	0.351 (4)	0.812 (2)	0.361 (2)	0.053 (6)*
H1O1	0.923 (5)	1.112 (3)	0.697 (2)	0.067 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0599 (3)	0.0476 (3)	0.0755 (4)	0.0236 (2)	−0.0016 (3)	0.0198 (2)
S1	0.0411 (2)	0.0433 (2)	0.0526 (3)	0.01215 (18)	−0.01336 (19)	−0.0029 (2)
O1	0.0620 (9)	0.0332 (6)	0.0643 (9)	0.0163 (6)	−0.0218 (7)	−0.0092 (6)
N1	0.0354 (7)	0.0336 (6)	0.0385 (7)	0.0079 (5)	−0.0034 (5)	0.0025 (5)
N2	0.0418 (8)	0.0345 (7)	0.0455 (8)	0.0131 (6)	−0.0099 (6)	−0.0037 (6)
N3	0.0386 (8)	0.0326 (7)	0.0442 (8)	0.0073 (6)	−0.0103 (6)	−0.0024 (6)
C1	0.0413 (9)	0.0304 (7)	0.0391 (8)	0.0071 (6)	−0.0004 (7)	0.0056 (6)
C2	0.0425 (9)	0.0381 (8)	0.0437 (9)	0.0122 (7)	0.0023 (7)	0.0135 (7)
C3	0.0428 (9)	0.0497 (10)	0.0425 (9)	0.0089 (8)	−0.0074 (7)	0.0125 (8)
C4	0.0482 (10)	0.0399 (9)	0.0374 (9)	0.0035 (7)	−0.0102 (7)	0.0025 (7)
C5	0.0438 (9)	0.0315 (7)	0.0375 (8)	0.0080 (6)	−0.0032 (7)	0.0039 (6)
C6	0.0352 (8)	0.0315 (7)	0.0331 (7)	0.0060 (6)	−0.0014 (6)	0.0048 (6)
C7	0.0373 (8)	0.0304 (7)	0.0397 (8)	0.0079 (6)	−0.0031 (6)	0.0031 (6)
C8	0.0343 (8)	0.0337 (7)	0.0359 (8)	0.0053 (6)	−0.0025 (6)	0.0022 (6)
C9	0.0380 (8)	0.0299 (7)	0.0375 (8)	0.0031 (6)	−0.0052 (6)	0.0017 (6)
C10	0.0534 (11)	0.0471 (10)	0.0459 (10)	−0.0019 (8)	0.0056 (8)	0.0068 (8)
C11	0.0676 (14)	0.0500 (12)	0.0622 (14)	−0.0190 (10)	0.0030 (11)	0.0095 (10)
C12	0.0915 (18)	0.0315 (9)	0.0574 (13)	−0.0017 (10)	−0.0096 (12)	0.0026 (8)
C13	0.0571 (12)	0.0421 (10)	0.0514 (11)	0.0067 (8)	0.0023 (9)	−0.0060 (8)
C14	0.0416 (9)	0.0368 (8)	0.0520 (11)	0.0021 (7)	0.0031 (8)	−0.0031 (8)

Geometric parameters (Å, º)

Cl1—C2	1.7408 (18)	C6—C7	1.459 (2)
S1—C8	1.6880 (17)	C7—H7A	0.9300
O1—C5	1.360 (2)	C9—C10	1.516 (3)
O1—H1O1	0.72 (3)	C9—C14	1.520 (2)
N1—C7	1.279 (2)	C9—H9A	0.9800
N1—N2	1.369 (2)	C10—C11	1.527 (3)
N2—C8	1.363 (2)	C10—H10A	0.9700
N2—H1N2	0.84 (2)	C10—H10B	0.9700
N3—C8	1.324 (2)	C11—C12	1.522 (4)
N3—C9	1.465 (2)	C11—H11A	0.9700
N3—H1N3	0.82 (2)	C11—H11B	0.9700
C1—C2	1.377 (2)	C12—C13	1.516 (3)
C1—C6	1.395 (2)	C12—H12A	0.9700
C1—H1A	0.9300	C12—H12B	0.9700
C2—C3	1.383 (3)	C13—C14	1.532 (3)
C3—C4	1.381 (3)	C13—H13A	0.9700
C3—H3A	0.9300	C13—H13B	0.9700
C4—C5	1.390 (2)	C14—H14A	0.9700
C4—H4A	0.9300	C14—H14B	0.9700
C5—C6	1.401 (2)
C5—O1—H1O1	112 (2)	C10—C9—C14	111.40 (16)
C7—N1—N2	115.26 (14)	N3—C9—H9A	108.3
C8—N2—N1	121.03 (14)	C10—C9—H9A	108.3
C8—N2—H1N2	117.6 (16)	C14—C9—H9A	108.3
N1—N2—H1N2	120.8 (16)	C9—C10—C11	110.06 (17)
C8—N3—C9	125.07 (15)	C9—C10—H10A	109.6
C8—N3—H1N3	116.3 (16)	C11—C10—H10A	109.6
C9—N3—H1N3	118.5 (16)	C9—C10—H10B	109.6
C2—C1—C6	119.89 (15)	C11—C10—H10B	109.6
C2—C1—H1A	120.1	H10A—C10—H10B	108.2
C6—C1—H1A	120.1	C12—C11—C10	111.10 (19)
C1—C2—C3	121.44 (16)	C12—C11—H11A	109.4
C1—C2—Cl1	119.06 (14)	C10—C11—H11A	109.4
C3—C2—Cl1	119.50 (14)	C12—C11—H11B	109.4
C4—C3—C2	119.17 (17)	C10—C11—H11B	109.4
C4—C3—H3A	120.4	H11A—C11—H11B	108.0
C2—C3—H3A	120.4	C13—C12—C11	110.60 (18)
C3—C4—C5	120.28 (16)	C13—C12—H12A	109.5
C3—C4—H4A	119.9	C11—C12—H12A	109.5
C5—C4—H4A	119.9	C13—C12—H12B	109.5
O1—C5—C4	122.65 (16)	C11—C12—H12B	109.5
O1—C5—C6	117.04 (15)	H12A—C12—H12B	108.1
C4—C5—C6	120.31 (15)	C12—C13—C14	111.10 (18)
C1—C6—C5	118.78 (15)	C12—C13—H13A	109.4
C1—C6—C7	121.50 (14)	C14—C13—H13A	109.4
C5—C6—C7	119.72 (14)	C12—C13—H13B	109.4
N1—C7—C6	121.37 (15)	C14—C13—H13B	109.4
N1—C7—H7A	119.3	H13A—C13—H13B	108.0
C6—C7—H7A	119.3	C9—C14—C13	110.17 (16)
N3—C8—N2	115.86 (15)	C9—C14—H14A	109.6
N3—C8—S1	125.09 (13)	C13—C14—H14A	109.6
N2—C8—S1	119.05 (13)	C9—C14—H14B	109.6
N3—C9—C10	111.42 (15)	C13—C14—H14B	109.6
N3—C9—C14	108.90 (14)	H14A—C14—H14B	108.1
C7—N1—N2—C8	−176.04 (17)	C5—C6—C7—N1	174.53 (17)
C6—C1—C2—C3	−2.4 (3)	C9—N3—C8—N2	176.67 (17)
C6—C1—C2—Cl1	178.29 (14)	C9—N3—C8—S1	−3.9 (3)
C1—C2—C3—C4	2.8 (3)	N1—N2—C8—N3	−5.5 (3)
Cl1—C2—C3—C4	−177.85 (16)	N1—N2—C8—S1	175.02 (14)
C2—C3—C4—C5	−0.1 (3)	C8—N3—C9—C10	−83.7 (2)
C3—C4—C5—O1	177.23 (19)	C8—N3—C9—C14	153.00 (19)
C3—C4—C5—C6	−3.0 (3)	N3—C9—C10—C11	−179.08 (18)
C2—C1—C6—C5	−0.8 (3)	C14—C9—C10—C11	−57.2 (2)
C2—C1—C6—C7	178.40 (17)	C9—C10—C11—C12	56.9 (3)
O1—C5—C6—C1	−176.81 (17)	C10—C11—C12—C13	−56.7 (3)
C4—C5—C6—C1	3.4 (3)	C11—C12—C13—C14	56.4 (3)
O1—C5—C6—C7	4.0 (3)	N3—C9—C14—C13	−179.75 (17)
C4—C5—C6—C7	−175.77 (17)	C10—C9—C14—C13	57.0 (2)
N2—N1—C7—C6	179.48 (16)	C12—C13—C14—C9	−56.3 (3)
C1—C6—C7—N1	−4.6 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O1^i	0.84 (2)	2.13 (2)	2.915 (2)	156 (2)
O1—H1O1···S1^i	0.73 (3)	2.48 (3)	3.128 (2)	150 (3)

Symmetry code: (i) −x+1, −y+2, −z+1.