2-Chloro-N-[4-(3-methyl-3-phenyl-cyclo-but-yl)-1,3-thia-zol-2-yl]-N'-(naphthalen-1-yl-methyl-idene)acetohydrazide.

In the mol-ecular structure of the title hydrazide derivative, C(27)H(24)ClN(3)OS, the acetohydrazide group is approximately planar, with a maximum deviation of 0.017 (3) Å. The dihedral angle between the naphthyl-ene system and the phenyl ring is 78.91 (18)°. The crystal structure is stabilized by one weak inter-molecular C-H⋯O hydrogen bond and two aliphatic C-H⋯π hydrogen-bonding associations.

Related literature

For the applications and bioactivity of hydrazide derivatives, see: Feng et al. (2006 ▶); Yang et al. (2007 ▶); Kamal et al. (2007 ▶); Masunari & Tavares (2007 ▶); Rando et al. (2002 ▶). For bond-length data, see: Demir et al. (2006 ▶).

Experimental

Crystal data

C27H24ClN3OS

M = 474.00

Monoclinic,

a = 7.498 (5) Å

b = 12.823 (5) Å

c = 24.924 (5) Å

β = 92.185 (5)°

V = 2394.6 (19) Å3

Z = 4

Mo Kα radiation

μ = 0.27 mm−1

T = 296 K

0.36 × 0.22 × 0.12 mm

Data collection

Stoe IPDS 2 CCD diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.797, T max = 0.961

12524 measured reflections

4206 independent reflections

1375 reflections with I > 2σ(I)

R int = 0.135

Refinement

R[F 2 > 2σ(F 2)] = 0.069

wR(F 2) = 0.156

S = 0.90

4206 reflections

298 parameters

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.16 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811000183/zs2087sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811000183/zs2087Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C27H24ClN3OS	F(000) = 992
Mr = 474.00	Dx = 1.315 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybc	Cell parameters from 9611 reflections
a = 7.498 (5) Å	θ = 1.6–27.3°
b = 12.823 (5) Å	µ = 0.27 mm−1
c = 24.924 (5) Å	T = 296 K
β = 92.185 (5)°	Prism, pale brown
V = 2394.6 (19) Å3	0.36 × 0.22 × 0.12 mm
Z = 4

Stoe IPDS 2 CCD diffractometer	4206 independent reflections
Radiation source: fine-focus sealed tube	1375 reflections with I > 2σ(I)
plane graphite	Rint = 0.135
rotation method scans	θmax = 25.0°, θmin = 1.6°
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	h = −8→7
Tmin = 0.797, Tmax = 0.961	k = −15→15
12524 measured reflections	l = −29→29

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)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.156	H-atom parameters constrained
S = 0.90	w = 1/[σ2(Fo2) + (0.0426P)2] where P = (Fo2 + 2Fc2)/3
4206 reflections	(Δ/σ)max < 0.001
298 parameters	Δρmax = 0.14 e Å−3
0 restraints	Δρmin = −0.16 e Å−3

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.

	x	y	z	Uiso*/Ueq
Cl1	0.1715 (3)	0.89358 (11)	0.38214 (7)	0.1256 (8)
S1	0.0165 (3)	0.51892 (13)	0.27709 (7)	0.1101 (7)
N1	0.2484 (6)	0.4174 (3)	0.33380 (17)	0.0726 (14)
N2	0.1837 (6)	0.5845 (3)	0.37084 (17)	0.0721 (14)
N3	0.2157 (6)	0.5688 (3)	0.42568 (17)	0.0760 (15)
O1	0.1257 (7)	0.7154 (3)	0.31249 (16)	0.1143 (18)
C1	0.7867 (12)	0.1538 (6)	0.3653 (3)	0.127 (3)
H1	0.8339	0.1724	0.3327	0.153*
C2	0.8984 (11)	0.1442 (7)	0.4126 (4)	0.140 (3)
H2	1.0198	0.1577	0.4106	0.168*
C3	0.8345 (13)	0.1166 (6)	0.4591 (4)	0.110 (3)
H3	0.9116	0.1100	0.4891	0.132*
C4	0.6583 (13)	0.0977 (5)	0.4638 (3)	0.103 (2)
H4	0.6128	0.0789	0.4966	0.123*
C5	0.5461 (9)	0.1073 (4)	0.4178 (3)	0.091 (2)
H5	0.4248	0.0943	0.4208	0.109*
C6	0.6064 (11)	0.1348 (4)	0.3692 (3)	0.0798 (18)
C8	0.4959 (9)	0.0466 (4)	0.2850 (2)	0.103 (2)
H7A	0.6192	0.0327	0.2789	0.155*
H7B	0.4325	0.0570	0.2513	0.155*
H7C	0.4452	−0.0114	0.3034	0.155*
C7	0.4812 (9)	0.1451 (4)	0.3194 (2)	0.0763 (18)
C9	0.4947 (9)	0.2463 (4)	0.2867 (2)	0.0884 (19)
H9A	0.5475	0.2368	0.2521	0.106*
H9B	0.5516	0.3033	0.3064	0.106*
C10	0.2863 (9)	0.1759 (4)	0.3310 (2)	0.0788 (18)
H10A	0.2016	0.1192	0.3261	0.095*
H10B	0.2737	0.2093	0.3656	0.095*
C11	0.2862 (9)	0.2530 (4)	0.2835 (2)	0.0811 (18)
H11	0.2394	0.2187	0.2508	0.097*
C12	0.1991 (8)	0.3552 (4)	0.2899 (2)	0.0748 (18)
C13	0.0734 (9)	0.3984 (4)	0.2568 (2)	0.097 (2)
H13	0.0241	0.3657	0.2264	0.117*
C14	0.1626 (8)	0.5056 (4)	0.3315 (2)	0.0730 (17)
C15	0.1622 (8)	0.6881 (4)	0.3572 (2)	0.082 (2)
C16	0.1878 (8)	0.7630 (4)	0.4043 (2)	0.0866 (19)
H16A	0.3040	0.7515	0.4217	0.104*
H16B	0.0976	0.7497	0.4303	0.104*
C17	0.2259 (8)	0.4801 (4)	0.4471 (2)	0.0809 (19)
H17	0.2139	0.4198	0.4265	0.097*
C18	0.2573 (8)	0.4748 (4)	0.5056 (2)	0.0760 (17)
C19	0.2719 (9)	0.5651 (5)	0.5343 (3)	0.108 (3)
H19	0.2600	0.6288	0.5167	0.129*
C20	0.3046 (11)	0.5631 (6)	0.5900 (3)	0.135 (3)
H20	0.3144	0.6255	0.6089	0.162*
C21	0.3222 (10)	0.4714 (7)	0.6168 (3)	0.123 (3)
H21	0.3454	0.4713	0.6537	0.148*
C22	0.3057 (8)	0.3774 (5)	0.5892 (2)	0.0807 (18)
C23	0.2711 (8)	0.3776 (4)	0.5329 (2)	0.0745 (17)
C24	0.2565 (8)	0.2805 (4)	0.5059 (2)	0.092 (2)
H24	0.2392	0.2786	0.4687	0.111*
C25	0.2679 (10)	0.1900 (5)	0.5343 (3)	0.106 (2)
H25	0.2522	0.1270	0.5163	0.127*
C26	0.3021 (10)	0.1887 (6)	0.5893 (3)	0.115 (3)
H26	0.3126	0.1257	0.6076	0.138*
C27	0.3200 (9)	0.2792 (7)	0.6158 (3)	0.106 (2)
H27	0.3424	0.2779	0.6527	0.127*

	U11	U22	U33	U12	U13	U23
Cl1	0.187 (2)	0.0619 (9)	0.1246 (15)	−0.0055 (11)	−0.0343 (14)	0.0081 (10)
S1	0.1371 (17)	0.1007 (12)	0.0888 (12)	0.0283 (12)	−0.0443 (12)	−0.0148 (10)
N1	0.097 (4)	0.059 (3)	0.061 (3)	0.004 (3)	−0.011 (3)	−0.002 (2)
N2	0.106 (4)	0.058 (3)	0.052 (3)	0.011 (3)	−0.002 (3)	0.003 (2)
N3	0.107 (4)	0.069 (3)	0.051 (3)	−0.006 (3)	−0.009 (3)	0.004 (2)
O1	0.190 (5)	0.081 (3)	0.069 (3)	0.020 (3)	−0.018 (3)	0.014 (2)
C1	0.104 (7)	0.186 (8)	0.093 (6)	−0.001 (6)	0.000 (6)	−0.024 (5)
C2	0.092 (7)	0.232 (10)	0.097 (6)	−0.001 (6)	0.000 (6)	−0.026 (7)
C3	0.111 (8)	0.120 (6)	0.097 (6)	0.024 (6)	−0.013 (6)	−0.029 (5)
C4	0.123 (7)	0.086 (4)	0.097 (6)	−0.002 (5)	−0.018 (5)	0.005 (4)
C5	0.112 (6)	0.079 (4)	0.080 (5)	−0.007 (4)	−0.014 (5)	0.003 (4)
C6	0.096 (6)	0.067 (4)	0.077 (5)	0.006 (4)	0.001 (4)	−0.017 (4)
C8	0.129 (6)	0.091 (4)	0.089 (5)	0.017 (4)	−0.008 (4)	−0.029 (4)
C7	0.094 (6)	0.068 (4)	0.067 (4)	0.004 (3)	0.000 (4)	−0.011 (3)
C9	0.106 (6)	0.083 (4)	0.077 (4)	−0.005 (4)	0.010 (4)	−0.016 (4)
C10	0.099 (6)	0.071 (3)	0.067 (4)	−0.004 (4)	0.002 (4)	−0.003 (3)
C11	0.110 (6)	0.064 (4)	0.069 (4)	0.000 (4)	−0.005 (4)	−0.007 (3)
C12	0.105 (5)	0.059 (3)	0.060 (4)	−0.006 (3)	0.002 (4)	−0.006 (3)
C13	0.128 (6)	0.096 (4)	0.067 (4)	0.004 (4)	−0.023 (4)	−0.013 (4)
C14	0.108 (5)	0.063 (4)	0.046 (3)	−0.003 (4)	−0.013 (3)	0.003 (3)
C15	0.112 (6)	0.064 (4)	0.069 (4)	0.007 (3)	−0.008 (4)	0.008 (3)
C16	0.114 (6)	0.061 (3)	0.084 (4)	0.006 (3)	−0.010 (4)	0.008 (3)
C17	0.126 (6)	0.067 (4)	0.048 (4)	−0.013 (4)	−0.012 (3)	0.011 (3)
C18	0.100 (5)	0.067 (4)	0.060 (4)	−0.009 (3)	−0.005 (3)	−0.003 (3)
C19	0.166 (8)	0.077 (4)	0.077 (5)	−0.001 (4)	−0.025 (5)	−0.007 (4)
C20	0.198 (9)	0.118 (6)	0.087 (6)	−0.016 (6)	−0.029 (6)	−0.023 (5)
C21	0.163 (8)	0.145 (7)	0.061 (5)	−0.014 (6)	−0.021 (5)	−0.007 (5)
C22	0.089 (5)	0.107 (5)	0.046 (4)	0.000 (4)	−0.003 (3)	0.012 (4)
C23	0.082 (5)	0.079 (4)	0.063 (4)	−0.006 (3)	−0.002 (3)	0.006 (3)
C24	0.126 (6)	0.078 (4)	0.071 (4)	0.008 (4)	−0.010 (4)	0.012 (4)
C25	0.145 (7)	0.082 (5)	0.091 (5)	0.006 (4)	−0.003 (5)	0.021 (4)
C26	0.128 (7)	0.108 (6)	0.108 (7)	0.008 (5)	0.005 (5)	0.037 (5)
C27	0.107 (6)	0.138 (6)	0.073 (5)	0.010 (5)	−0.006 (4)	0.032 (5)

Cl1—C16	1.766 (5)	C10—C11	1.541 (7)
S1—C13	1.686 (6)	C10—H10A	0.9700
S1—C14	1.720 (5)	C10—H10B	0.9700
N1—C14	1.301 (6)	C11—C12	1.476 (7)
N1—C12	1.392 (6)	C11—H11	0.9800
N2—C15	1.379 (6)	C12—C13	1.349 (7)
N2—N3	1.393 (5)	C13—H13	0.9300
N2—C14	1.412 (6)	C15—C16	1.523 (7)
N3—C17	1.257 (5)	C16—H16A	0.9700
O1—C15	1.190 (6)	C16—H16B	0.9700
C1—C6	1.380 (9)	C17—C18	1.470 (7)
C1—C2	1.425 (9)	C17—H17	0.9300
C1—H1	0.9300	C18—C19	1.364 (7)
C2—C3	1.321 (9)	C18—C23	1.422 (7)
C2—H2	0.9300	C19—C20	1.403 (8)
C3—C4	1.353 (9)	C19—H19	0.9300
C3—H3	0.9300	C20—C21	1.356 (8)
C4—C5	1.401 (8)	C20—H20	0.9300
C4—H4	0.9300	C21—C22	1.391 (8)
C5—C6	1.356 (8)	C21—H21	0.9300
C5—H5	0.9300	C22—C23	1.417 (7)
C6—C7	1.532 (8)	C22—C27	1.425 (8)
C8—C7	1.532 (6)	C23—C24	1.418 (7)
C8—H7A	0.9600	C24—C25	1.361 (7)
C8—H7B	0.9600	C24—H24	0.9300
C8—H7C	0.9600	C25—C26	1.384 (8)
C7—C9	1.539 (7)	C25—H25	0.9300
C7—C10	1.552 (7)	C26—C27	1.340 (8)
C9—C11	1.565 (8)	C26—H26	0.9300
C9—H9A	0.9700	C27—H27	0.9300
C9—H9B	0.9700
C13—S1—C14	89.2 (3)	C9—C11—H11	110.0
C14—N1—C12	110.4 (4)	C13—C12—N1	113.8 (5)
C15—N2—N3	113.2 (4)	C13—C12—C11	126.9 (5)
C15—N2—C14	120.6 (4)	N1—C12—C11	119.3 (5)
N3—N2—C14	126.0 (4)	C12—C13—S1	111.8 (4)
C17—N3—N2	123.5 (4)	C12—C13—H13	124.1
C6—C1—C2	118.2 (8)	S1—C13—H13	124.1
C6—C1—H1	120.9	N1—C14—N2	123.4 (4)
C2—C1—H1	120.9	N1—C14—S1	114.8 (4)
C3—C2—C1	121.9 (8)	N2—C14—S1	121.8 (4)
C3—C2—H2	119.1	O1—C15—N2	122.4 (5)
C1—C2—H2	119.1	O1—C15—C16	123.6 (5)
C2—C3—C4	120.8 (8)	N2—C15—C16	114.1 (5)
C2—C3—H3	119.6	C15—C16—Cl1	110.6 (4)
C4—C3—H3	119.6	C15—C16—H16A	109.5
C3—C4—C5	118.2 (8)	Cl1—C16—H16A	109.5
C3—C4—H4	120.9	C15—C16—H16B	109.5
C5—C4—H4	120.9	Cl1—C16—H16B	109.5
C6—C5—C4	122.9 (7)	H16A—C16—H16B	108.1
C6—C5—H5	118.5	N3—C17—C18	117.9 (5)
C4—C5—H5	118.5	N3—C17—H17	121.0
C5—C6—C1	118.0 (6)	C18—C17—H17	121.0
C5—C6—C7	122.0 (7)	C19—C18—C23	119.4 (5)
C1—C6—C7	119.9 (7)	C19—C18—C17	119.1 (5)
C7—C8—H7A	109.5	C23—C18—C17	121.5 (5)
C7—C8—H7B	109.5	C18—C19—C20	120.8 (6)
H7A—C8—H7B	109.5	C18—C19—H19	119.6
C7—C8—H7C	109.5	C20—C19—H19	119.6
H7A—C8—H7C	109.5	C21—C20—C19	120.9 (6)
H7B—C8—H7C	109.5	C21—C20—H20	119.6
C6—C7—C8	109.1 (5)	C19—C20—H20	119.6
C6—C7—C9	116.8 (5)	C20—C21—C22	120.2 (6)
C8—C7—C9	113.0 (5)	C20—C21—H21	119.9
C6—C7—C10	115.1 (5)	C22—C21—H21	119.9
C8—C7—C10	113.7 (5)	C21—C22—C23	119.9 (6)
C9—C7—C10	88.0 (4)	C21—C22—C27	122.1 (6)
C7—C9—C11	89.2 (5)	C23—C22—C27	118.0 (6)
C7—C9—H9A	113.8	C22—C23—C24	118.5 (5)
C11—C9—H9A	113.8	C22—C23—C18	118.9 (5)
C7—C9—H9B	113.8	C24—C23—C18	122.7 (5)
C11—C9—H9B	113.8	C25—C24—C23	119.9 (5)
H9A—C9—H9B	111.0	C25—C24—H24	120.0
C11—C10—C7	89.7 (5)	C23—C24—H24	120.0
C11—C10—H10A	113.7	C24—C25—C26	122.2 (7)
C7—C10—H10A	113.7	C24—C25—H25	118.9
C11—C10—H10B	113.7	C26—C25—H25	118.9
C7—C10—H10B	113.7	C27—C26—C25	119.2 (7)
H10A—C10—H10B	110.9	C27—C26—H26	120.4
C12—C11—C10	118.3 (5)	C25—C26—H26	120.4
C12—C11—C9	119.2 (5)	C26—C27—C22	122.2 (6)
C10—C11—C9	87.4 (4)	C26—C27—H27	118.9
C12—C11—H11	110.0	C22—C27—H27	118.9
C10—C11—H11	110.0
C15—N2—N3—C17	174.5 (6)	C15—N2—C14—N1	149.7 (6)
C14—N2—N3—C17	−1.6 (9)	N3—N2—C14—N1	−34.4 (9)
C6—C1—C2—C3	0.9 (12)	C15—N2—C14—S1	−31.5 (8)
C1—C2—C3—C4	−1.0 (13)	N3—N2—C14—S1	144.4 (5)
C2—C3—C4—C5	0.6 (12)	C13—S1—C14—N1	0.5 (5)
C3—C4—C5—C6	−0.2 (10)	C13—S1—C14—N2	−178.4 (5)
C4—C5—C6—C1	0.1 (10)	N3—N2—C15—O1	−176.4 (6)
C4—C5—C6—C7	−179.9 (5)	C14—N2—C15—O1	0.0 (10)
C2—C1—C6—C5	−0.4 (10)	N3—N2—C15—C16	3.1 (7)
C2—C1—C6—C7	179.5 (6)	C14—N2—C15—C16	179.4 (5)
C5—C6—C7—C8	−100.5 (7)	O1—C15—C16—Cl1	−4.2 (9)
C1—C6—C7—C8	79.6 (7)	N2—C15—C16—Cl1	176.3 (4)
C5—C6—C7—C9	129.9 (6)	N2—N3—C17—C18	−179.0 (5)
C1—C6—C7—C9	−50.1 (8)	N3—C17—C18—C19	0.8 (9)
C5—C6—C7—C10	28.7 (8)	N3—C17—C18—C23	−179.8 (6)
C1—C6—C7—C10	−151.2 (6)	C23—C18—C19—C20	1.6 (10)
C6—C7—C9—C11	−135.0 (6)	C17—C18—C19—C20	−179.0 (7)
C8—C7—C9—C11	97.2 (5)	C18—C19—C20—C21	−0.1 (13)
C10—C7—C9—C11	−17.8 (4)	C19—C20—C21—C22	−0.8 (13)
C6—C7—C10—C11	136.9 (5)	C20—C21—C22—C23	0.2 (11)
C8—C7—C10—C11	−96.2 (5)	C20—C21—C22—C27	−178.8 (8)
C9—C7—C10—C11	18.1 (4)	C21—C22—C23—C24	179.5 (6)
C7—C10—C11—C12	−139.8 (5)	C27—C22—C23—C24	−1.4 (9)
C7—C10—C11—C9	−17.8 (4)	C21—C22—C23—C18	1.2 (9)
C7—C9—C11—C12	139.1 (5)	C27—C22—C23—C18	−179.7 (6)
C7—C9—C11—C10	17.9 (4)	C19—C18—C23—C22	−2.1 (9)
C14—N1—C12—C13	−1.6 (7)	C17—C18—C23—C22	178.5 (6)
C14—N1—C12—C11	177.6 (5)	C19—C18—C23—C24	179.7 (6)
C10—C11—C12—C13	−127.6 (7)	C17—C18—C23—C24	0.3 (9)
C9—C11—C12—C13	128.4 (6)	C22—C23—C24—C25	2.9 (9)
C10—C11—C12—N1	53.3 (8)	C18—C23—C24—C25	−178.9 (6)
C9—C11—C12—N1	−50.8 (7)	C23—C24—C25—C26	−3.2 (11)
N1—C12—C13—S1	2.0 (7)	C24—C25—C26—C27	1.8 (12)
C11—C12—C13—S1	−177.2 (5)	C25—C26—C27—C22	−0.3 (12)
C14—S1—C13—C12	−1.4 (5)	C21—C22—C27—C26	179.2 (8)
C12—N1—C14—N2	179.4 (5)	C23—C22—C27—C26	0.2 (10)
C12—N1—C14—S1	0.5 (6)

Cg1 and Cg2 are the centroids of the C12/C13/S1/C14/N1 and C22–C27 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O1i	0.93	2.41	3.243 (7)	148.
C8—H7A···Cg1ii	0.96	2.94	3.748 (3)	143
C16—H16B···Cg2iii	0.97	2.93	3.740 (8)	142

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C12/C13/S1/C14/N1 and C22–C27 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O1i	0.93	2.41	3.243 (7)	148
C8—H7A⋯Cg1ii	0.96	2.94	3.748 (3)	143
C16—H16B⋯Cg2iii	0.97	2.93	3.740 (8)	142

Symmetry codes: (i) ; (ii) ; (iii) .