Investigation of the mol­ecular structure of 4-(3-methyl-3-phenyl­cyclo­but­yl)-2-[2-(3-methyl­benzyl­idene)hydrazin­yl]thia­zole in the gas and solid phases

Karakurt, T.

doi:10.1107/S2053229618013475

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Investigation of the molecular structure of 4-(3-methyl-3-phenylcyclobutyl)-2-[2-(3-methylbenzylidene)hydrazinyl]thiazole in the gas and solid phases

T. Karakurt

In this study, the title Shiff base, C₂₂H₂₃N₃S, was synthesized and examined by ¹H and ¹³C NMR spectroscopy and X-ray analysis techniques. The crystal structure is stabilized by classical intermolecular N—H

N hydrogen bonding. The crystal packing is additionally stabilized by C—H

π interactions. It has been observed that the compound can exist in two different tautomeric forms, and experimental and theoretical studies were carried out on these tautomeric structures. For this purpose, the gas phase of the compound was optimized by density functional theory (DFT) using the B3LYP/6-311G(d) method, which allowed for the structural parameters (bond angles, bond lengths and dihedral angles), as well as the frontier molecular orbitals (FMO), to be examined. In addition, stable structures of the two tautomers in the solid phase were obtained using Quantum ESPRESSO under periodic boundary conditions (PBC).

Keywords: Schiff base; DFT; tautomer; PBC; quantum ESPRESSO; crystal structure.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229618013475/fn3273sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229618013475/fn3273Isup2.hkl Contains datablock I

CCDC reference: 1830817

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015b); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

4-(3-Methyl-3-phenylcyclobutyl)-2-[2-(3-methylbenzylidene)hydrazinyl]thiazole top

Crystal data top

C₂₂H₂₃N₃S	F(000) = 1536
M_r = 361.49	D_x = 1.225 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 20.135 (6) Å	Cell parameters from 9110 reflections
b = 6.826 (2) Å	θ = 2.3–27.5°
c = 29.027 (9) Å	µ = 0.18 mm⁻¹
β = 100.759 (14)°	T = 296 K
V = 3920 (2) Å³	Yellow, square
Z = 8	0.30 × 0.25 × 0.20 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	R_int = 0.030
phi and ω scans	θ_max = 28.5°, θ_min = 2.1°
37086 measured reflections	h = −26→23
4808 independent reflections	k = −8→9
3768 reflections with I > 2σ(I)	l = −38→38

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.053	Hydrogen site location: mixed
wR(F²) = 0.139	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ²(F_o²) + (0.0587P)² + 3.2259P] where P = (F_o² + 2F_c²)/3
4808 reflections	(Δ/σ)_max = 0.001
241 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Special details top

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	U_iso*/U_eq
S1	0.58902 (2)	0.56865 (8)	0.48351 (2)	0.05323 (16)
N1	0.70748 (7)	0.4780 (2)	0.46802 (5)	0.0422 (3)
N3	0.60750 (7)	0.2186 (2)	0.53558 (5)	0.0476 (4)
N2	0.65668 (8)	0.2373 (2)	0.50859 (6)	0.0487 (4)
C12	0.69121 (8)	0.6635 (3)	0.44866 (6)	0.0424 (4)
C14	0.65816 (8)	0.4144 (3)	0.48732 (6)	0.0424 (4)
C7	0.74959 (9)	0.9158 (3)	0.35970 (6)	0.0455 (4)
C10	0.73941 (9)	0.7662 (3)	0.42417 (6)	0.0438 (4)
H10	0.784422	0.768443	0.444097	0.053*
C9	0.72094 (10)	0.9717 (3)	0.40406 (6)	0.0460 (4)
H9A	0.745584	1.076540	0.422312	0.055*
H9B	0.672748	0.998004	0.397767	0.055*
C1	0.70844 (9)	0.9818 (3)	0.31335 (6)	0.0506 (5)
C15	0.59881 (9)	0.0498 (3)	0.55155 (7)	0.0513 (4)
H15	0.623028	−0.055860	0.543012	0.062*
C13	0.63081 (9)	0.7336 (3)	0.45386 (6)	0.0498 (4)
H13	0.613674	0.854947	0.442950	0.060*
C11	0.74476 (10)	0.6988 (3)	0.37375 (6)	0.0512 (4)
H11A	0.785119	0.623283	0.372290	0.061*
H11B	0.704628	0.632721	0.357270	0.061*
C16	0.55110 (9)	0.0188 (3)	0.58330 (7)	0.0519 (5)
C17	0.53565 (9)	0.1666 (3)	0.61245 (7)	0.0561 (5)
H17	0.553888	0.290805	0.610552	0.067*
C8	0.82230 (10)	0.9849 (4)	0.36365 (7)	0.0631 (6)
H8A	0.823214	1.125294	0.361829	0.095*
H8B	0.841166	0.930028	0.338492	0.095*
H8C	0.848384	0.943057	0.393122	0.095*
C2	0.68400 (11)	1.1711 (4)	0.30784 (8)	0.0654 (6)
H2A	0.693676	1.258780	0.332708	0.079*
C18	0.49354 (10)	0.1324 (4)	0.64436 (7)	0.0677 (6)
C6	0.69462 (12)	0.8568 (4)	0.27516 (7)	0.0684 (6)
H6	0.711498	0.729665	0.277792	0.082*
C22	0.52187 (12)	−0.1646 (4)	0.58526 (9)	0.0716 (6)
H22	0.531490	−0.265086	0.565886	0.086*
C20	0.46580 (11)	−0.0527 (5)	0.64543 (9)	0.0822 (8)
H20	0.437762	−0.078927	0.666763	0.099*
C5	0.65620 (15)	0.9183 (6)	0.23331 (8)	0.0923 (9)
H5	0.647496	0.832394	0.208031	0.111*
C21	0.47859 (13)	−0.1969 (5)	0.61603 (11)	0.0870 (8)
H21	0.457949	−0.318478	0.616694	0.104*
C3	0.64509 (13)	1.2321 (4)	0.26558 (10)	0.0848 (8)
H3	0.628690	1.359669	0.262285	0.102*
C4	0.63096 (14)	1.1029 (6)	0.22863 (10)	0.0963 (10)
H4	0.604147	1.142175	0.200516	0.116*
C19	0.47894 (17)	0.2921 (6)	0.67679 (10)	0.1083 (11)
H19A	0.516064	0.382644	0.682282	0.162*
H19B	0.472999	0.235628	0.706034	0.162*
H19C	0.438443	0.359962	0.662735	0.162*
H2	0.6956 (12)	0.156 (3)	0.5147 (7)	0.063 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0409 (2)	0.0575 (3)	0.0635 (3)	0.0010 (2)	0.0154 (2)	0.0054 (2)
N1	0.0404 (7)	0.0455 (8)	0.0417 (7)	−0.0034 (6)	0.0100 (6)	0.0008 (6)
N3	0.0419 (8)	0.0524 (9)	0.0505 (8)	−0.0037 (7)	0.0143 (6)	0.0032 (7)
N2	0.0448 (8)	0.0480 (9)	0.0571 (9)	−0.0021 (7)	0.0193 (7)	0.0046 (7)
C12	0.0415 (9)	0.0480 (10)	0.0361 (8)	−0.0021 (7)	0.0031 (7)	0.0003 (7)
C14	0.0396 (8)	0.0483 (10)	0.0392 (8)	−0.0045 (7)	0.0071 (7)	−0.0052 (7)
C7	0.0447 (9)	0.0534 (10)	0.0383 (8)	−0.0092 (8)	0.0076 (7)	−0.0015 (8)
C10	0.0416 (9)	0.0495 (10)	0.0394 (8)	−0.0040 (7)	0.0055 (7)	0.0006 (7)
C9	0.0546 (10)	0.0447 (10)	0.0390 (9)	−0.0066 (8)	0.0089 (7)	−0.0015 (7)
C1	0.0434 (9)	0.0692 (13)	0.0396 (9)	−0.0152 (9)	0.0091 (7)	0.0047 (8)
C15	0.0450 (10)	0.0510 (11)	0.0594 (11)	−0.0044 (8)	0.0138 (8)	0.0019 (9)
C13	0.0464 (10)	0.0518 (11)	0.0508 (10)	0.0014 (8)	0.0077 (8)	0.0075 (8)
C11	0.0565 (11)	0.0508 (11)	0.0482 (10)	−0.0031 (8)	0.0151 (8)	−0.0037 (8)
C16	0.0379 (9)	0.0629 (12)	0.0550 (11)	−0.0043 (8)	0.0086 (8)	0.0107 (9)
C17	0.0390 (9)	0.0749 (14)	0.0538 (11)	−0.0008 (9)	0.0072 (8)	0.0135 (10)
C8	0.0488 (11)	0.0813 (15)	0.0575 (12)	−0.0114 (10)	0.0058 (9)	0.0056 (11)
C2	0.0671 (13)	0.0688 (14)	0.0587 (12)	−0.0125 (11)	0.0076 (10)	0.0155 (11)
C18	0.0431 (10)	0.1099 (19)	0.0509 (11)	0.0090 (12)	0.0105 (9)	0.0191 (12)
C6	0.0653 (13)	0.0923 (17)	0.0469 (11)	−0.0110 (12)	0.0087 (10)	−0.0096 (11)
C22	0.0629 (13)	0.0709 (15)	0.0829 (16)	−0.0151 (11)	0.0190 (12)	0.0136 (12)
C20	0.0481 (12)	0.132 (2)	0.0695 (15)	−0.0040 (14)	0.0182 (11)	0.0417 (16)
C5	0.0819 (18)	0.145 (3)	0.0450 (12)	−0.0263 (19)	−0.0007 (12)	−0.0066 (16)
C21	0.0658 (15)	0.099 (2)	0.099 (2)	−0.0225 (14)	0.0208 (14)	0.0323 (17)
C3	0.0689 (15)	0.0942 (19)	0.0875 (18)	−0.0076 (14)	0.0053 (13)	0.0429 (16)
C4	0.0670 (16)	0.153 (3)	0.0607 (15)	−0.0277 (19)	−0.0087 (12)	0.0318 (18)
C19	0.100 (2)	0.156 (3)	0.0807 (18)	0.020 (2)	0.0474 (17)	0.006 (2)

Geometric parameters (Å, º) top

S1—C13	1.728 (2)	C16—C17	1.389 (3)
S1—C14	1.7325 (19)	C16—C22	1.389 (3)
N1—C14	1.302 (2)	C17—C18	1.387 (3)
N1—C12	1.400 (2)	C17—H17	0.9300
N3—C15	1.266 (2)	C8—H8A	0.9600
N3—N2	1.378 (2)	C8—H8B	0.9600
N2—C14	1.361 (2)	C8—H8C	0.9600
N2—H2	0.95 (2)	C2—C3	1.390 (3)
C12—C13	1.341 (3)	C2—H2A	0.9300
C12—C10	1.482 (2)	C18—C20	1.384 (4)
C7—C1	1.511 (3)	C18—C19	1.505 (4)
C7—C8	1.522 (3)	C6—C5	1.378 (4)
C7—C11	1.544 (3)	C6—H6	0.9300
C7—C9	1.554 (2)	C22—C21	1.377 (3)
C10—C9	1.539 (3)	C22—H22	0.9300
C10—C11	1.557 (2)	C20—C21	1.359 (4)
C10—H10	0.9800	C20—H20	0.9300
C9—H9A	0.9700	C5—C4	1.356 (5)
C9—H9B	0.9700	C5—H5	0.9300
C1—C2	1.381 (3)	C21—H21	0.9300
C1—C6	1.385 (3)	C3—C4	1.376 (4)
C15—C16	1.466 (3)	C3—H3	0.9300
C15—H15	0.9300	C4—H4	0.9300
C13—H13	0.9300	C19—H19A	0.9600
C11—H11A	0.9700	C19—H19B	0.9600
C11—H11B	0.9700	C19—H19C	0.9600

C13—S1—C14	88.15 (9)	C17—C16—C22	119.00 (19)
C14—N1—C12	109.52 (15)	C17—C16—C15	121.74 (18)
C15—N3—N2	117.07 (16)	C22—C16—C15	119.2 (2)
C14—N2—N3	114.77 (15)	C18—C17—C16	121.3 (2)
C14—N2—H2	121.0 (13)	C18—C17—H17	119.4
N3—N2—H2	119.8 (13)	C16—C17—H17	119.4
C13—C12—N1	115.25 (16)	C7—C8—H8A	109.5
C13—C12—C10	125.06 (17)	C7—C8—H8B	109.5
N1—C12—C10	119.68 (15)	H8A—C8—H8B	109.5
N1—C14—N2	125.06 (16)	C7—C8—H8C	109.5
N1—C14—S1	115.99 (14)	H8A—C8—H8C	109.5
N2—C14—S1	118.93 (13)	H8B—C8—H8C	109.5
C1—C7—C8	109.54 (15)	C1—C2—C3	120.8 (2)
C1—C7—C11	118.03 (15)	C1—C2—H2A	119.6
C8—C7—C11	112.62 (17)	C3—C2—H2A	119.6
C1—C7—C9	115.98 (16)	C20—C18—C17	117.9 (2)
C8—C7—C9	111.24 (15)	C20—C18—C19	121.4 (2)
C11—C7—C9	88.01 (13)	C17—C18—C19	120.7 (3)
C12—C10—C9	118.65 (15)	C5—C6—C1	120.9 (3)
C12—C10—C11	118.54 (15)	C5—C6—H6	119.5
C9—C10—C11	88.10 (13)	C1—C6—H6	119.5
C12—C10—H10	109.9	C21—C22—C16	119.7 (3)
C9—C10—H10	109.9	C21—C22—H22	120.2
C11—C10—H10	109.9	C16—C22—H22	120.2
C10—C9—C7	89.40 (14)	C21—C20—C18	121.5 (2)
C10—C9—H9A	113.7	C21—C20—H20	119.2
C7—C9—H9A	113.7	C18—C20—H20	119.2
C10—C9—H9B	113.7	C4—C5—C6	120.6 (3)
C7—C9—H9B	113.7	C4—C5—H5	119.7
H9A—C9—H9B	111.0	C6—C5—H5	119.7
C2—C1—C6	118.0 (2)	C20—C21—C22	120.6 (3)
C2—C1—C7	120.40 (18)	C20—C21—H21	119.7
C6—C1—C7	121.6 (2)	C22—C21—H21	119.7
N3—C15—C16	120.89 (18)	C4—C3—C2	119.7 (3)
N3—C15—H15	119.6	C4—C3—H3	120.1
C16—C15—H15	119.6	C2—C3—H3	120.1
C12—C13—S1	111.09 (15)	C5—C4—C3	119.9 (3)
C12—C13—H13	124.5	C5—C4—H4	120.1
S1—C13—H13	124.5	C3—C4—H4	120.1
C7—C11—C10	89.07 (13)	C18—C19—H19A	109.5
C7—C11—H11A	113.8	C18—C19—H19B	109.5
C10—C11—H11A	113.8	H19A—C19—H19B	109.5
C7—C11—H11B	113.8	C18—C19—H19C	109.5
C10—C11—H11B	113.8	H19A—C19—H19C	109.5
H11A—C11—H11B	111.0	H19B—C19—H19C	109.5

C15—N3—N2—C14	171.86 (16)	C14—S1—C13—C12	0.56 (15)
C14—N1—C12—C13	0.0 (2)	C1—C7—C11—C10	−135.92 (16)
C14—N1—C12—C10	−179.40 (14)	C8—C7—C11—C10	94.86 (17)
C12—N1—C14—N2	178.65 (16)	C9—C7—C11—C10	−17.36 (13)
C12—N1—C14—S1	0.47 (18)	C12—C10—C11—C7	139.41 (16)
N3—N2—C14—N1	165.93 (16)	C9—C10—C11—C7	17.54 (14)
N3—N2—C14—S1	−15.9 (2)	N3—C15—C16—C17	−27.8 (3)
C13—S1—C14—N1	−0.61 (14)	N3—C15—C16—C22	154.0 (2)
C13—S1—C14—N2	−178.91 (15)	C22—C16—C17—C18	2.1 (3)
C13—C12—C10—C9	1.9 (3)	C15—C16—C17—C18	−176.13 (18)
N1—C12—C10—C9	−178.81 (14)	C6—C1—C2—C3	1.8 (3)
C13—C12—C10—C11	−102.9 (2)	C7—C1—C2—C3	−178.87 (19)
N1—C12—C10—C11	76.5 (2)	C16—C17—C18—C20	−1.7 (3)
C12—C10—C9—C7	−139.20 (15)	C16—C17—C18—C19	178.1 (2)
C11—C10—C9—C7	−17.43 (13)	C2—C1—C6—C5	−1.6 (3)
C1—C7—C9—C10	137.98 (16)	C7—C1—C6—C5	179.1 (2)
C8—C7—C9—C10	−95.97 (17)	C17—C16—C22—C21	−0.3 (3)
C11—C7—C9—C10	17.58 (13)	C15—C16—C22—C21	178.0 (2)
C8—C7—C1—C2	−80.5 (2)	C17—C18—C20—C21	−0.6 (3)
C11—C7—C1—C2	148.82 (18)	C19—C18—C20—C21	179.7 (3)
C9—C7—C1—C2	46.4 (2)	C1—C6—C5—C4	−0.1 (4)
C8—C7—C1—C6	98.8 (2)	C18—C20—C21—C22	2.4 (4)
C11—C7—C1—C6	−31.8 (3)	C16—C22—C21—C20	−1.9 (4)
C9—C7—C1—C6	−134.30 (19)	C1—C2—C3—C4	−0.3 (4)
N2—N3—C15—C16	175.61 (16)	C6—C5—C4—C3	1.6 (4)
N1—C12—C13—S1	−0.4 (2)	C2—C3—C4—C5	−1.4 (4)
C10—C12—C13—S1	178.91 (13)

Calculated and experimental geometric parameters (Å, °)of the crystal in T1 form top

	Experimental (T1 form)	Experimental (T2 form)	Gaussian-DFT (B3LYP/6-311G(d) (T1 form)	Quantum ESPRESSO (T1 form)
Bond lengths
C1—C2	1.381 (3)	1.383 (4)	1.399	1.391
C1—C6	1.385 (3)	1.384 (4)	1.399	1.388
C6—C5	1.378 (4)	1.384 (4)	1.393	1.386
C12—C13	1.341 (3)	1.339 (3)	1.360	1.361
S1—C14	1.732 (2)	1.734 (2)	1.756	1.730
S1—C13	1.728 (2)	1.728 (2)	1.752	1.717
N1—C12	1.399 (2)	1.395 (2)	1.386	1.379
N1—C14	1.302 (2)	1.298 (3)	1.298	1.312
N2—C14	1.360 (2)	1.362 (3)	1.372	1.345
C10—C9	1.538 (3)	1.537 (3)	1.549	1.527
C10—C11	1.557 (3)	1.558 (3)	1.558	1.546
C12—C10	1.482 (3)	1.483 (3)	1.495	1.472
C7—C9	1.554 (3)	1.555 (3)	1.565	1.543
C7—C11	1.544 (3)	1.542 (3)	1.564	1.538
N2—N3	1.379 (2)	1.387 (3)	1.344	1.335
N3—C15	1.266 (3)	1.266 (3)	1.284	1.285

Bond Angles
C15—N3—N2	117.1 (2)	116.6 (2)	118.4	118.11
C14—N2—N3	114.8 (1)	114.1 (2)	121.4	115.90
N1—C14—N2	125.1 (2)	125.1 (2)	122.3	125.85
N1—C14—S1	116.0 (1)	115.5 (1)	116.0	115.33
C13—S1—C14	88.14 (9)	88.2 (1)	87.3	88.35
C2—C1—C6	118.0 (2)	118.2 (2)	118.1	118.82
C11—C7—C9	88.0 (1)	88.0 (2)	87.8	88.33
C10—C9—C7	89.4 (1)	89.4 (2)	89.2	89.0

Torsion angles
N1—C12—C10—C9	-178.8 (2)	-178.8 (2)	174.2	179.83
N1—C12—C13—S1	-0.4 (2)	-0.4 (2)	-0.1	0.79
N3—C15—C16—C17	-27.8 (3)	-27.9 (3)	0.1	27.17
C12—N1—C14—S1	0.5 (2)	0.4 (2)	-0.2	-1.59
C14—S1—C13—C12	0.6 (1)	0.5 (2)	-0.1	-1.35

Hydrogen-bond geometry for the crystal in T1 form (Å, °). Cg3 and Cg4 are the centroids of the ??? and ??? rings, repsectively. top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···N1ⁱ	0.95 (2)	2.13 (2)	3.067 (2)	169.6 (18)
C4—H4···Cg4ⁱⁱ	0.93	2.99	3.797 (3)	146
C10—H10···Cg3ⁱⁱⁱ	0.98	2.82	3.605 (2)	137
C13—H13···Cg4^iv	0.93	2.91	3.657 (2)	139

Symmetry codes: (i) -x+3/2, -y+1/2, -z+1; (ii) x, -y+1, z-1/2; (iii) -x+3/2, -y+3/2, -z+1; (iv) -x+1, -y+1, -z+1.

Energies of the T1 and T2 forms of the title compound in Hartrees, and energy differences, activation energies in kJ mol^-1 top

T1 (a.u.)	T2 (a.u.)	TS (a.u.)	Δ E (kJ mol^-1)	E_a(f) (kJ mol^-1)	E_a(r) (kJ mol^-1)
-1414.826434	-1414.808633	-1414.747792	-46.28	158.19	204.47

Comparison of the experimental and optimized unit-cell parameters calculated by QE-VC-Relax method of T1 form of crystal top

Parameter	Experimental	QE-VC-Relax/DFT
Space group	C2/c	C2/c
a (Å)	20.135 (6)	19.181
b (Å)	6.826 (2)	6.874
c (Å)	29.027 (9)	28.273
α (°)	90	90
β (°)	100.759 (14)	103.237
γ (°)	90	90
Z	4	4
V (Å³)	3920 (2)	3629

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Investigation of the mol­ecular structure of 4-(3-methyl-3-phenyl­cyclo­but­yl)-2-[2-(3-methyl­benzyl­idene)hydrazin­yl]thia­zole in the gas and solid phases

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Investigation of the molecular structure of 4-(3-methyl-3-phenylcyclobutyl)-2-[2-(3-methylbenzylidene)hydrazinyl]thiazole in the gas and solid phases