2-[5-(4-Meth­oxy­phen­yl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl]-6-methyl-1,3-benzothia­zole

Fun, H.-K.; Arshad, S.; Himaja, M.; Munirajasekhar, D.; Sarojini, B.K.

doi:10.1107/S1600536811033666

organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page o2412

doi:10.1107/S1600536811033666

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2-[5-(4-Methoxyphenyl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl]-6-methyl-1,3-benzothiazole

Hoong-Kun Fun,^a ^*‡ Suhana Arshad,^a M. Himaja,^b D. Munirajasekhar ^b and B. K. Sarojini ^c

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bChemistry Division, School of Advanced Sciences, VIT University, Vellore 632014, Tamil Nadu, India, and ^cDepartment of Chemistry, P. A. College of Engineering, Nadupadavu, D. K., Mangalore, India
^*Correspondence e-mail: hkfun@usm.my

(Received 16 August 2011; accepted 18 August 2011; online 27 August 2011)

In the title compound, C₂₄H₂₁N₃OS, the pyrazole ring makes dihedral angles of 5.40 (7) and 6.72 (8)° with the benzo[d]thiazole ring system and the benzene ring, respectively, and a dihedral angle of 85.72 (8)° with the methoxy-substituted benzene ring. In the crystal structure, the molecules are linked by C—H⋯π interactions.

Related literature

For background to the properties and applications of pyrazolines, see: Taylor et al. (1992 ); Rajendera Prasad et al. (2005 ). For reference bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₂₄H₂₁N₃OS
M_r = 399.50
Orthorhombic, P b c n
a = 22.632 (3) Å
b = 11.1961 (12) Å
c = 16.1137 (18) Å
V = 4083.1 (8) Å³
Z = 8
Mo Kα radiation
μ = 0.18 mm⁻¹
T = 296 K
0.37 × 0.24 × 0.19 mm

Data collection

Bruker SMART APEXII DUO CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.936, T_max = 0.967
25081 measured reflections
5949 independent reflections
3835 reflections with I > 2σ(I)
R_int = 0.041

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.123
S = 1.00
5949 reflections
264 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the S1/C17/N1/C18/C23, C1–C6 and C10–C15 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15A⋯Cg1ⁱ	0.93	2.91	3.6318 (17)	138
C22—H22A⋯Cg2ⁱ	0.93	2.89	3.6438 (18)	140
C2—H2A⋯Cg3ⁱⁱ	0.93	2.74	3.4884 (18)	138
Symmetry codes: (i) $[x+{\script{3\over 2}}, -y+{\script{1\over 2}}, -z]$ ; (ii) $[x, -y-1, z-{\script{1\over 2}}]$ .

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

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811033666/hb6368sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811033666/hb6368Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811033666/hb6368Isup3.cml

checkCIF report

Comment top

Pyrazolines are an important class of heterocyclic compounds, some of which exhibit important pharmacological activities such as antitumor (Taylor et al., 1992) and antidepressant (Rajendera Prasad et al., 2005) agents. The title compound, (I), was synthesized by the condensation of 1-(6-methylbenzo[d]thiazol-2-yl)hydrazine with (E)-3-(4-methoxyphenyl)-1-phenylprop-2-en-1-one in presence of ethanol and its crystal structure is now described.

In the molecular structure (Fig 1), the pyrazole ring (N2/N3/C7–C9) is approximately planar with the benzo[d]thiozole ring system (S1/N1/C17–C23) and the benzene ring (C1–C6) with dihedral angles of 5.40 (7)° and 6.72 (8)°, respectively. On the other hand, the pyrazole ring (N2/N3/C7–C9) is approximately perpendicular to the methoxy substituted benzene ring (C10–C15) with dihedral angle of 85.72 (8)°. The bond lengths (Allen et al., 1987) and angles are within normal ranges.

The crystal packing is shown in Fig. 2. The crystal structure is stabilized by the intermolecular C15–H15A···Cg1, C22—H22A···Cg2 and C2—H2A···Cg3 (Table 1) interactions (Cg1, Cg2 and Cg3 are the centroids of S1/C17/N1/C18/C23, C1—C6 and C10—C15 rings, respectively).

Related literature top

For background to the properties and applications of pyrazolines, see: Taylor et al. (1992); Rajendera Prasad et al. (2005). For reference bond-length data, see: Allen et al. (1987).

Experimental top

A mixture of (E)-3-(4-methoxyphenyl)-1-phenylprop-2-en-1-one (5 mmol) and 1-(6-methylbenzo[d]thiazol-2-yl)hydrazine (5 mmol) was refluxed for 16 h in ethanol (20 ml). After completion of the reaction, the reaction mixture was poured into cold water. The precipitate obtained was filtered and washed with cold water. The product was recrystalized from ethanol to yield colourless blocks of (I) and dried. m.p. 131–132 °C, HRMS Calcd for C₂₄H₂₁N₃OS 399.5080 found 399.5079.

Computing details top

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

Figures top

	Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids.
	Fig. 2. The crystal packing of the title compound.

2-[5-(4-Methoxyphenyl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl]-6-methyl- 1,3-benzothiazole top

Crystal data top

C₂₄H₂₁N₃OS	F(000) = 1680
M_r = 399.50	D_x = 1.300 Mg m⁻³
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 4472 reflections
a = 22.632 (3) Å	θ = 2.4–27.1°
b = 11.1961 (12) Å	µ = 0.18 mm⁻¹
c = 16.1137 (18) Å	T = 296 K
V = 4083.1 (8) Å³	Block, colourless
Z = 8	0.37 × 0.24 × 0.19 mm

Data collection top

Bruker SMART APEXII DUO CCD diffractometer	5949 independent reflections
Radiation source: fine-focus sealed tube	3835 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
ϕ and ω scans	θ_max = 30.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −31→31
T_min = 0.936, T_max = 0.967	k = −15→10
25081 measured reflections	l = −22→18

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.123	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0593P)² + 0.3403P] where P = (F_o² + 2F_c²)/3
5949 reflections	(Δ/σ)_max = 0.002
264 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₂₄H₂₁N₃OS	V = 4083.1 (8) Å³
M_r = 399.50	Z = 8
Orthorhombic, Pbcn	Mo Kα radiation
a = 22.632 (3) Å	µ = 0.18 mm⁻¹
b = 11.1961 (12) Å	T = 296 K
c = 16.1137 (18) Å	0.37 × 0.24 × 0.19 mm

Data collection top

Bruker SMART APEXII DUO CCD diffractometer	5949 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3835 reflections with I > 2σ(I)
T_min = 0.936, T_max = 0.967	R_int = 0.041
25081 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.123	H-atom parameters constrained
S = 1.00	Δρ_max = 0.25 e Å⁻³
5949 reflections	Δρ_min = −0.29 e Å⁻³
264 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
S1	0.537594 (17)	−0.00428 (3)	0.11748 (3)	0.04063 (11)
N1	0.51267 (5)	0.20397 (10)	0.05137 (8)	0.0394 (3)
N2	0.43376 (5)	0.11316 (10)	0.11985 (8)	0.0408 (3)
N3	0.41278 (5)	0.01631 (10)	0.16416 (8)	0.0382 (3)
O1	0.43721 (6)	0.61031 (10)	0.32050 (8)	0.0589 (3)
C1	0.26306 (7)	−0.02592 (14)	0.24336 (11)	0.0463 (4)
H1A	0.2459	0.0437	0.2231	0.056*
C2	0.22952 (7)	−0.10444 (16)	0.29063 (11)	0.0529 (4)
H2A	0.1902	−0.0867	0.3023	0.063*
C3	0.25414 (8)	−0.20806 (16)	0.32013 (11)	0.0537 (4)
H3A	0.2315	−0.2608	0.3514	0.064*
C4	0.31269 (8)	−0.23390 (15)	0.30326 (11)	0.0535 (4)
H4A	0.3293	−0.3041	0.3235	0.064*
C5	0.34660 (7)	−0.15656 (13)	0.25674 (10)	0.0450 (4)
H5A	0.3859	−0.1748	0.2456	0.054*
C6	0.32201 (6)	−0.05056 (12)	0.22615 (9)	0.0378 (3)
C7	0.35724 (6)	0.03383 (12)	0.17774 (10)	0.0377 (3)
C8	0.33397 (7)	0.14714 (13)	0.13926 (10)	0.0427 (4)
H8A	0.3117	0.1938	0.1792	0.051*
H8B	0.3091	0.1301	0.0917	0.051*
C9	0.39093 (6)	0.21231 (12)	0.11292 (10)	0.0384 (3)
H9A	0.3879	0.2390	0.0552	0.046*
C10	0.40585 (6)	0.31648 (12)	0.16894 (9)	0.0340 (3)
C11	0.39769 (7)	0.43310 (13)	0.14186 (10)	0.0423 (4)
H11A	0.3851	0.4470	0.0878	0.051*
C12	0.40797 (8)	0.52875 (14)	0.19391 (10)	0.0471 (4)
H12A	0.4020	0.6062	0.1749	0.056*
C13	0.42714 (6)	0.50954 (13)	0.27438 (10)	0.0396 (3)
C14	0.43514 (7)	0.39440 (13)	0.30260 (10)	0.0411 (3)
H14A	0.4477	0.3807	0.3567	0.049*
C15	0.42441 (7)	0.29915 (13)	0.24975 (10)	0.0399 (3)
H15A	0.4298	0.2217	0.2691	0.048*
C16	0.45090 (10)	0.5966 (2)	0.40532 (13)	0.0768 (6)
H16A	0.4569	0.6737	0.4299	0.115*
H16B	0.4863	0.5499	0.4109	0.115*
H16C	0.4189	0.5567	0.4329	0.115*
C17	0.49059 (6)	0.11551 (12)	0.09394 (9)	0.0348 (3)
C18	0.57140 (6)	0.17917 (13)	0.03344 (9)	0.0388 (3)
C19	0.60917 (8)	0.25405 (16)	−0.01089 (10)	0.0508 (4)
H19A	0.5956	0.3265	−0.0317	0.061*
C20	0.66700 (8)	0.21907 (17)	−0.02351 (11)	0.0550 (4)
H20A	0.6919	0.2688	−0.0538	0.066*
C21	0.68940 (7)	0.11232 (16)	0.00738 (10)	0.0498 (4)
C22	0.65199 (7)	0.03749 (15)	0.05197 (10)	0.0455 (4)
H22A	0.6660	−0.0343	0.0734	0.055*
C23	0.59353 (6)	0.07106 (13)	0.06414 (9)	0.0375 (3)
C24	0.75341 (8)	0.0795 (2)	−0.00596 (13)	0.0688 (5)
H24A	0.7616	0.0046	0.0207	0.103*
H24B	0.7782	0.1405	0.0173	0.103*
H24C	0.7611	0.0727	−0.0644	0.103*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0411 (2)	0.03568 (19)	0.0451 (2)	−0.00003 (15)	0.00495 (16)	0.00259 (15)
N1	0.0411 (7)	0.0400 (7)	0.0372 (7)	−0.0024 (5)	0.0005 (5)	0.0015 (5)
N2	0.0386 (7)	0.0320 (6)	0.0519 (8)	−0.0002 (5)	0.0072 (6)	0.0028 (5)
N3	0.0376 (6)	0.0334 (6)	0.0435 (8)	−0.0027 (5)	0.0044 (5)	−0.0023 (5)
O1	0.0692 (8)	0.0499 (7)	0.0575 (8)	0.0019 (6)	−0.0072 (6)	−0.0192 (6)
C1	0.0370 (7)	0.0434 (8)	0.0585 (11)	−0.0011 (6)	−0.0023 (7)	−0.0003 (7)
C2	0.0336 (8)	0.0619 (11)	0.0631 (12)	−0.0049 (7)	0.0055 (7)	−0.0002 (9)
C3	0.0483 (9)	0.0560 (10)	0.0568 (11)	−0.0135 (8)	0.0059 (8)	0.0069 (8)
C4	0.0527 (10)	0.0435 (9)	0.0642 (12)	−0.0015 (7)	0.0048 (8)	0.0091 (8)
C5	0.0399 (8)	0.0400 (8)	0.0551 (10)	0.0008 (6)	0.0041 (7)	−0.0010 (7)
C6	0.0353 (7)	0.0369 (7)	0.0411 (9)	−0.0048 (6)	−0.0001 (6)	−0.0053 (6)
C7	0.0359 (7)	0.0348 (7)	0.0423 (9)	−0.0030 (6)	−0.0017 (6)	−0.0057 (6)
C8	0.0356 (7)	0.0377 (8)	0.0548 (10)	−0.0020 (6)	−0.0040 (7)	−0.0013 (7)
C9	0.0388 (7)	0.0360 (7)	0.0405 (8)	0.0002 (6)	−0.0031 (6)	0.0009 (6)
C10	0.0311 (7)	0.0339 (7)	0.0369 (8)	0.0001 (5)	−0.0003 (6)	0.0027 (6)
C11	0.0536 (9)	0.0375 (8)	0.0358 (8)	0.0010 (6)	−0.0030 (7)	0.0059 (6)
C12	0.0623 (10)	0.0324 (7)	0.0465 (10)	0.0029 (7)	0.0002 (8)	0.0036 (6)
C13	0.0337 (7)	0.0419 (8)	0.0434 (9)	0.0010 (6)	0.0013 (6)	−0.0056 (7)
C14	0.0370 (7)	0.0487 (8)	0.0374 (8)	0.0031 (6)	−0.0052 (6)	0.0008 (6)
C15	0.0399 (8)	0.0372 (7)	0.0425 (9)	0.0025 (6)	−0.0052 (6)	0.0062 (6)
C16	0.0759 (14)	0.0946 (16)	0.0600 (13)	0.0059 (12)	−0.0087 (11)	−0.0341 (12)
C17	0.0376 (7)	0.0346 (7)	0.0322 (8)	−0.0022 (6)	−0.0009 (6)	−0.0048 (6)
C18	0.0409 (8)	0.0436 (8)	0.0319 (8)	−0.0050 (6)	0.0007 (6)	−0.0028 (6)
C19	0.0548 (10)	0.0510 (10)	0.0466 (10)	−0.0072 (7)	0.0057 (8)	0.0075 (8)
C20	0.0513 (10)	0.0659 (11)	0.0477 (10)	−0.0166 (8)	0.0107 (8)	0.0010 (8)
C21	0.0401 (8)	0.0671 (11)	0.0422 (9)	−0.0069 (8)	0.0043 (7)	−0.0114 (8)
C22	0.0420 (8)	0.0516 (9)	0.0429 (9)	0.0011 (7)	0.0006 (7)	−0.0048 (7)
C23	0.0399 (7)	0.0413 (8)	0.0314 (8)	−0.0042 (6)	0.0021 (6)	−0.0019 (6)
C24	0.0437 (9)	0.0941 (15)	0.0686 (13)	−0.0049 (10)	0.0110 (9)	−0.0166 (11)

Geometric parameters (Å, º) top

S1—C23	1.7473 (15)	C9—H9A	0.9800
S1—C17	1.7534 (15)	C10—C15	1.382 (2)
N1—C17	1.3042 (18)	C10—C11	1.3891 (19)
N1—C18	1.3884 (19)	C11—C12	1.380 (2)
N2—C17	1.3525 (18)	C11—H11A	0.9300
N2—N3	1.3824 (16)	C12—C13	1.384 (2)
N2—C9	1.4780 (18)	C12—H12A	0.9300
N3—C7	1.2909 (18)	C13—C14	1.379 (2)
O1—C13	1.3701 (17)	C14—C15	1.386 (2)
O1—C16	1.410 (2)	C14—H14A	0.9300
C1—C2	1.389 (2)	C15—H15A	0.9300
C1—C6	1.390 (2)	C16—H16A	0.9600
C1—H1A	0.9300	C16—H16B	0.9600
C2—C3	1.372 (2)	C16—H16C	0.9600
C2—H2A	0.9300	C18—C19	1.394 (2)
C3—C4	1.383 (2)	C18—C23	1.400 (2)
C3—H3A	0.9300	C19—C20	1.381 (2)
C4—C5	1.379 (2)	C19—H19A	0.9300
C4—H4A	0.9300	C20—C21	1.390 (3)
C5—C6	1.400 (2)	C20—H20A	0.9300
C5—H5A	0.9300	C21—C22	1.391 (2)
C6—C7	1.462 (2)	C21—C24	1.510 (2)
C7—C8	1.507 (2)	C22—C23	1.389 (2)
C8—C9	1.541 (2)	C22—H22A	0.9300
C8—H8A	0.9700	C24—H24A	0.9600
C8—H8B	0.9700	C24—H24B	0.9600
C9—C10	1.513 (2)	C24—H24C	0.9600

C23—S1—C17	87.93 (7)	C11—C12—C13	120.11 (14)
C17—N1—C18	108.92 (12)	C11—C12—H12A	119.9
C17—N2—N3	120.09 (11)	C13—C12—H12A	119.9
C17—N2—C9	125.85 (12)	O1—C13—C14	124.69 (14)
N3—N2—C9	113.76 (11)	O1—C13—C12	115.62 (13)
C7—N3—N2	107.63 (12)	C14—C13—C12	119.69 (13)
C13—O1—C16	118.20 (14)	C13—C14—C15	119.58 (14)
C2—C1—C6	120.55 (15)	C13—C14—H14A	120.2
C2—C1—H1A	119.7	C15—C14—H14A	120.2
C6—C1—H1A	119.7	C10—C15—C14	121.61 (13)
C3—C2—C1	120.21 (15)	C10—C15—H15A	119.2
C3—C2—H2A	119.9	C14—C15—H15A	119.2
C1—C2—H2A	119.9	O1—C16—H16A	109.5
C2—C3—C4	119.85 (15)	O1—C16—H16B	109.5
C2—C3—H3A	120.1	H16A—C16—H16B	109.5
C4—C3—H3A	120.1	O1—C16—H16C	109.5
C5—C4—C3	120.58 (16)	H16A—C16—H16C	109.5
C5—C4—H4A	119.7	H16B—C16—H16C	109.5
C3—C4—H4A	119.7	N1—C17—N2	122.78 (13)
C4—C5—C6	120.16 (15)	N1—C17—S1	117.53 (11)
C4—C5—H5A	119.9	N2—C17—S1	119.69 (10)
C6—C5—H5A	119.9	N1—C18—C19	124.98 (14)
C1—C6—C5	118.64 (14)	N1—C18—C23	116.23 (13)
C1—C6—C7	120.11 (14)	C19—C18—C23	118.78 (14)
C5—C6—C7	121.25 (13)	C20—C19—C18	119.07 (16)
N3—C7—C6	121.56 (13)	C20—C19—H19A	120.5
N3—C7—C8	113.48 (13)	C18—C19—H19A	120.5
C6—C7—C8	124.96 (13)	C19—C20—C21	122.44 (15)
C7—C8—C9	102.69 (12)	C19—C20—H20A	118.8
C7—C8—H8A	111.2	C21—C20—H20A	118.8
C9—C8—H8A	111.2	C20—C21—C22	118.73 (15)
C7—C8—H8B	111.2	C20—C21—C24	120.51 (16)
C9—C8—H8B	111.2	C22—C21—C24	120.74 (17)
H8A—C8—H8B	109.1	C23—C22—C21	119.32 (16)
N2—C9—C10	112.80 (12)	C23—C22—H22A	120.3
N2—C9—C8	99.91 (11)	C21—C22—H22A	120.3
C10—C9—C8	112.79 (12)	C22—C23—C18	121.65 (14)
N2—C9—H9A	110.3	C22—C23—S1	128.96 (12)
C10—C9—H9A	110.3	C18—C23—S1	109.38 (11)
C8—C9—H9A	110.3	C21—C24—H24A	109.5
C15—C10—C11	117.93 (13)	C21—C24—H24B	109.5
C15—C10—C9	121.45 (12)	H24A—C24—H24B	109.5
C11—C10—C9	120.50 (13)	C21—C24—H24C	109.5
C12—C11—C10	121.07 (15)	H24A—C24—H24C	109.5
C12—C11—H11A	119.5	H24B—C24—H24C	109.5
C10—C11—H11A	119.5

C17—N2—N3—C7	−177.07 (13)	C11—C12—C13—O1	178.73 (15)
C9—N2—N3—C7	8.82 (17)	C11—C12—C13—C14	−0.9 (2)
C6—C1—C2—C3	−0.7 (3)	O1—C13—C14—C15	−178.95 (14)
C1—C2—C3—C4	0.5 (3)	C12—C13—C14—C15	0.6 (2)
C2—C3—C4—C5	−0.2 (3)	C11—C10—C15—C14	−0.5 (2)
C3—C4—C5—C6	0.1 (3)	C9—C10—C15—C14	−176.56 (13)
C2—C1—C6—C5	0.6 (2)	C13—C14—C15—C10	0.1 (2)
C2—C1—C6—C7	−178.78 (15)	C18—N1—C17—N2	−179.24 (13)
C4—C5—C6—C1	−0.3 (2)	C18—N1—C17—S1	0.64 (16)
C4—C5—C6—C7	179.05 (15)	N3—N2—C17—N1	179.42 (13)
N2—N3—C7—C6	−177.70 (13)	C9—N2—C17—N1	−7.2 (2)
N2—N3—C7—C8	2.31 (17)	N3—N2—C17—S1	−0.46 (18)
C1—C6—C7—N3	176.59 (15)	C9—N2—C17—S1	172.88 (11)
C5—C6—C7—N3	−2.8 (2)	C23—S1—C17—N1	−0.27 (12)
C1—C6—C7—C8	−3.4 (2)	C23—S1—C17—N2	179.61 (12)
C5—C6—C7—C8	177.19 (14)	C17—N1—C18—C19	−179.67 (15)
N3—C7—C8—C9	−11.49 (17)	C17—N1—C18—C23	−0.79 (18)
C6—C7—C8—C9	168.52 (13)	N1—C18—C19—C20	179.20 (15)
C17—N2—C9—C10	−68.81 (19)	C23—C18—C19—C20	0.3 (2)
N3—N2—C9—C10	104.90 (14)	C18—C19—C20—C21	−0.9 (3)
C17—N2—C9—C8	171.19 (14)	C19—C20—C21—C22	0.6 (3)
N3—N2—C9—C8	−15.11 (16)	C19—C20—C21—C24	−178.27 (17)
C7—C8—C9—N2	14.51 (15)	C20—C21—C22—C23	0.2 (2)
C7—C8—C9—C10	−105.50 (14)	C24—C21—C22—C23	179.10 (15)
N2—C9—C10—C15	−42.67 (19)	C21—C22—C23—C18	−0.8 (2)
C8—C9—C10—C15	69.62 (17)	C21—C22—C23—S1	−179.64 (12)
N2—C9—C10—C11	141.35 (14)	N1—C18—C23—C22	−178.48 (13)
C8—C9—C10—C11	−106.37 (16)	C19—C18—C23—C22	0.5 (2)
C15—C10—C11—C12	0.2 (2)	N1—C18—C23—S1	0.60 (16)
C9—C10—C11—C12	176.33 (14)	C19—C18—C23—S1	179.55 (12)
C10—C11—C12—C13	0.5 (2)	C17—S1—C23—C22	178.81 (15)
C16—O1—C13—C14	−6.9 (2)	C17—S1—C23—C18	−0.18 (11)
C16—O1—C13—C12	173.59 (16)

Hydrogen-bond geometry (Å, º) top

Cg1, Cg2 and Cg3 are the centroids of the S1/C17/N1/C18/C23, C1–C6 and C10–C15 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···Cg1ⁱ	0.93	2.91	3.6318 (17)	138
C22—H22A···Cg2ⁱ	0.93	2.89	3.6438 (18)	140
C2—H2A···Cg3ⁱⁱ	0.93	2.74	3.4884 (18)	138

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

Experimental details

Crystal data
Chemical formula	C₂₄H₂₁N₃OS
M_r	399.50
Crystal system, space group	Orthorhombic, Pbcn
Temperature (K)	296
a, b, c (Å)	22.632 (3), 11.1961 (12), 16.1137 (18)
V (Å³)	4083.1 (8)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.18
Crystal size (mm)	0.37 × 0.24 × 0.19

Data collection
Diffractometer	Bruker SMART APEXII DUO CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.936, 0.967
No. of measured, independent and observed [I > 2σ(I)] reflections	25081, 5949, 3835
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.704

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.123, 1.00
No. of reflections	5949
No. of parameters	264
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.29

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1, Cg2 and Cg3 are the centroids of the S1/C17/N1/C18/C23, C1–C6 and C10–C15 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···Cg1ⁱ	0.93	2.91	3.6318 (17)	138
C22—H22A···Cg2ⁱ	0.93	2.89	3.6438 (18)	140
C2—H2A···Cg3ⁱⁱ	0.93	2.74	3.4884 (18)	138

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

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

The authors thank Universiti Sains Malaysia (USM) for a Research University Grant (No. 1001/PFIZIK/811160). SA thanks the Malaysian government and USM for the award of a research scholarship.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–S19. CrossRef Web of Science Google Scholar
Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Rajendera Prasad, Y., Lakshmana Rao, A., Prasoona, L., Murali, K. & Ravi Kumar, P. (2005). Bioorg. Med. Chem. Lett. 15, 5030–5034. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Taylor, E. C., Patel, H. & Kumar, H. (1992). Tetrahedron, 48, 8089–8100. CrossRef CAS Web of Science Google Scholar

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Volume 67| Part 9| September 2011| Page o2412

doi:10.1107/S1600536811033666

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

2-[5-(4-Meth­­oxy­phen­yl)-3-phenyl-4,5-di­hydro-1H-pyrazol-1-yl]-6-methyl-1,3-benzo­thia­zole

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

2-[5-(4-Methoxyphenyl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl]-6-methyl-1,3-benzothiazole