2-Chloro-N-[4-(3-methyl-3-phenyl­cyclo­but­yl)-1,3-thia­zol-2-yl]-N′-(naphthalen-1-yl­methyl­idene)acetohydrazide

Inkaya, E.; Dinçer, M.; Çukurovalı, A.; Yılmaz, E.

doi:10.1107/S1600536811000183

2-Chloro-N-[4-(3-methyl-3-phenylcyclobutyl)-1,3-thiazol-2-yl]-N′-(naphthalen-1-ylmethylidene)acetohydrazide

E. Inkaya, M. Dinçer, A. Çukurovalı and E. Yılmaz

In the molecular structure of the title hydrazide derivative, C₂₇H₂₄ClN₃OS, the acetohydrazide group is approximately planar, with a maximum deviation of 0.017 (3) Å. The dihedral angle between the naphthylene system and the phenyl ring is 78.91 (18)°. The crystal structure is stabilized by one weak intermolecular C—H

O hydrogen bond and two aliphatic C—H

π hydrogen-bonding associations.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536811000183/zs2087sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536811000183/zs2087Isup2.hkl Contains datablock I

CCDC reference: 811288

checkCIF report

Key indicators

Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.010 Å
R factor = 0.069
wR factor = 0.156
Data-to-parameter ratio = 14.1

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low ....         33 Perc.

Alert level C
RINTA01_ALERT_3_C  The value of Rint is greater than 0.12
            Rint given   0.135
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         S1
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C1
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C2
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C20
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C21
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C6
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C16
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C22
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds (x 1000) Ang ..         10
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.595          8
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....          1
PLAT153_ALERT_1_C The su's on the Cell Axes   are Equal (x 100000)        500 Ang.

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
  13 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   8 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Hydrazide derivatives of various compounds are very important units in host–guest chemistry due to their special arrangement of donor-acceptor functional groups (Feng et al., 2006; Yang et al., 2007). Hydrazine derivatives have also been associated with remarkable anticancer (Kamal et al., 2007), antibacterial (Masunari & Tavares, 2007) and tuberculostatic (Rando et al., 2002) activities. The title compound, the hydrazide derivative C₂₇H₂₄N₃OClS (I) has been synthesized and its crystal structure is reported here.

In the structure of (I) (Fig. 1) the phenyl and thiazole rings are cis-related with respect to the cyclobutane ring. The dihedral angle between the naphthylene fragment with the thiazole and phenyl rings are 35.76 (17)° and 78.91 (18)°, respectively. The cyclobutane ring is puckered, with a dihedral angle of 25.20 (5)° between the two three-membered halves of the ring. The dihedral angle between the acetohydrazide group and the thiazole ring is 32.28 (38)°. The C═O bond distance is 1.190 (6) Å comparing with a literature value of 1.187 (16) Å (Demir et al., 2006).

The crystal packing involves a weak intermolecular thiazole C13—H···O1 hydrogen bond (Table 1, Fig. 2) and intermoleculer C8—H···π (thiazole ring C12/C13/S1/C14/N1), C16—H···π (ring C22—C27) hydrogen-bonding associations (Fig. 3).

Related literature top

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 top

The synthesis of the title compound was simply carried out in the following reaction (Fig. 4). A solution of 0.3975 gram (1 mmol) of N-[4-(3-methyl-3-phenyl-cyclobutyl)-thiazol-2-yl]-N-naphthalen -1-ylmethylenehydrazine was dissolved in 20 ml of dioxane containing 1 mmol triethylamine. To this solution, 90 µL (1 mmol) of chloroacetyl chloride solution in 20 ml 1,4-dioxane was added dropwise over a two hour period at room temperature with stirring. Mixture was stirred two hours more and then neutralized with 5% aqueous ammonia. The compound thus precipitated was filtered, washed with copious water and crystallized from ethanol, giving brown crystals (yield, 93%).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); 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).

Figures top

	Fig. 1. An ORTEP-3 (Farrugia, 1997) drawing of (I), showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. Part of the crystal structure of the title compound, showing the C—H···O hydrogen bonding. For clarity, only H atoms involved in hydrogen bonding have been included. For symmetry codes, see Table 1.
	Fig. 3. Part of the crystal structure of the title compound, showing the C—H···π interactions. For clarity, only H atoms involved in hydrogen bonding have been included. For symmetry codes, see Table 1.
	Fig. 4. Reaction scheme for the title compound.

2-Chloro-N-[4-(3-methyl-3-phenylcyclobutyl)-1,3-thiazol-2-yl]- N'-(naphthalen-1-ylmethylidene)acetohydrazide top

Crystal data top

C₂₇H₂₄ClN₃OS	F(000) = 992
M_r = 474.00	D_x = 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

Data collection top

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

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)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.156	H-atom parameters constrained
S = 0.90	w = 1/[σ²(F_o²) + (0.0426P)²] where P = (F_o² + 2F_c²)/3
4206 reflections	(Δ/σ)_max < 0.001
298 parameters	Δρ_max = 0.14 e Å⁻³
0 restraints	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₂₇H₂₄ClN₃OS	V = 2394.6 (19) Å³
M_r = 474.00	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.498 (5) Å	µ = 0.27 mm⁻¹
b = 12.823 (5) Å	T = 296 K
c = 24.924 (5) Å	0.36 × 0.22 × 0.12 mm
β = 92.185 (5)°

Data collection top

Stoe IPDS 2 CCD diffractometer	4206 independent reflections
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	1375 reflections with I > 2σ(I)
T_min = 0.797, T_max = 0.961	R_int = 0.135
12524 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.069	0 restraints
wR(F²) = 0.156	H-atom parameters constrained
S = 0.90	Δρ_max = 0.14 e Å⁻³
4206 reflections	Δρ_min = −0.16 e Å⁻³
298 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x, y−1/2, −z+1/2; (ii) −x+1, y−1/2, −z+1/2; (iii) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₇H₂₄ClN₃OS
M_r	474.00
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	7.498 (5), 12.823 (5), 24.924 (5)
β (°)	92.185 (5)
V (Å³)	2394.6 (19)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.36 × 0.22 × 0.12

Data collection
Diffractometer	Stoe IPDS 2 CCD diffractometer
Absorption correction	Integration (X-RED32; Stoe & Cie, 2002)
T_min, T_max	0.797, 0.961
No. of measured, independent and observed [I > 2σ(I)] reflections	12524, 4206, 1375
R_int	0.135
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.069, 0.156, 0.90
No. of reflections	4206
No. of parameters	298
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.16

Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).