Literature DB >> 22065664

2-[5-(4-Meth-oxy-phen-yl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl]-6-methyl-1,3-benzothia-zole.

Hoong-Kun Fun, Suhana Arshad, M Himaja, D Munirajasekhar, B K Sarojini.   

Abstract

In the title compound, C(24)H(21)N(3)OS, the n class="Chemical">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 meth-oxy-substituted benzene ring. In the crystal structure, the mol-ecules are linked by C-H⋯π inter-actions.

Entities:  

Year:  2011        PMID： 22065664      PMCID： PMC3200767          DOI： 10.1107/S1600536811033666

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


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 = 399.50 Orthorhombic, 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[F 2 > 2σ(F 2)] = 0.041 wR(F 2) = 0.123 S = 1.00 5949 reflections 264 parameters H-atom parameters constrained Δρmax = 0.25 e Å−3 Δρmin = −0.29 e Å−3 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 ▶). Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811033666/hb6368sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811033666/hb6368Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536811033666/hb6368Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C24H21N3OSF(000) = 1680
Mr = 399.50Dx = 1.300 Mg m−3
Orthorhombic, PbcnMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2abCell parameters from 4472 reflections
a = 22.632 (3) Åθ = 2.4–27.1°
b = 11.1961 (12) ŵ = 0.18 mm−1
c = 16.1137 (18) ÅT = 296 K
V = 4083.1 (8) Å3Block, colourless
Z = 80.37 × 0.24 × 0.19 mm
Bruker SMART APEXII DUO CCD diffractometer5949 independent reflections
Radiation source: fine-focus sealed tube3835 reflections with I > 2σ(I)
graphiteRint = 0.041
φ and ω scansθmax = 30.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)h = −31→31
Tmin = 0.936, Tmax = 0.967k = −15→10
25081 measured reflectionsl = −22→18
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123H-atom parameters constrained
S = 1.00w = 1/[σ2(Fo2) + (0.0593P)2 + 0.3403P] where P = (Fo2 + 2Fc2)/3
5949 reflections(Δ/σ)max = 0.002
264 parametersΔρmax = 0.25 e Å−3
0 restraintsΔρmin = −0.29 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.
xyzUiso*/Ueq
S10.537594 (17)−0.00428 (3)0.11748 (3)0.04063 (11)
N10.51267 (5)0.20397 (10)0.05137 (8)0.0394 (3)
N20.43376 (5)0.11316 (10)0.11985 (8)0.0408 (3)
N30.41278 (5)0.01631 (10)0.16416 (8)0.0382 (3)
O10.43721 (6)0.61031 (10)0.32050 (8)0.0589 (3)
C10.26306 (7)−0.02592 (14)0.24336 (11)0.0463 (4)
H1A0.24590.04370.22310.056*
C20.22952 (7)−0.10444 (16)0.29063 (11)0.0529 (4)
H2A0.1902−0.08670.30230.063*
C30.25414 (8)−0.20806 (16)0.32013 (11)0.0537 (4)
H3A0.2315−0.26080.35140.064*
C40.31269 (8)−0.23390 (15)0.30326 (11)0.0535 (4)
H4A0.3293−0.30410.32350.064*
C50.34660 (7)−0.15656 (13)0.25674 (10)0.0450 (4)
H5A0.3859−0.17480.24560.054*
C60.32201 (6)−0.05056 (12)0.22615 (9)0.0378 (3)
C70.35724 (6)0.03383 (12)0.17774 (10)0.0377 (3)
C80.33397 (7)0.14714 (13)0.13926 (10)0.0427 (4)
H8A0.31170.19380.17920.051*
H8B0.30910.13010.09170.051*
C90.39093 (6)0.21231 (12)0.11292 (10)0.0384 (3)
H9A0.38790.23900.05520.046*
C100.40585 (6)0.31648 (12)0.16894 (9)0.0340 (3)
C110.39769 (7)0.43310 (13)0.14186 (10)0.0423 (4)
H11A0.38510.44700.08780.051*
C120.40797 (8)0.52875 (14)0.19391 (10)0.0471 (4)
H12A0.40200.60620.17490.056*
C130.42714 (6)0.50954 (13)0.27438 (10)0.0396 (3)
C140.43514 (7)0.39440 (13)0.30260 (10)0.0411 (3)
H14A0.44770.38070.35670.049*
C150.42441 (7)0.29915 (13)0.24975 (10)0.0399 (3)
H15A0.42980.22170.26910.048*
C160.45090 (10)0.5966 (2)0.40532 (13)0.0768 (6)
H16A0.45690.67370.42990.115*
H16B0.48630.54990.41090.115*
H16C0.41890.55670.43290.115*
C170.49059 (6)0.11551 (12)0.09394 (9)0.0348 (3)
C180.57140 (6)0.17917 (13)0.03344 (9)0.0388 (3)
C190.60917 (8)0.25405 (16)−0.01089 (10)0.0508 (4)
H19A0.59560.3265−0.03170.061*
C200.66700 (8)0.21907 (17)−0.02351 (11)0.0550 (4)
H20A0.69190.2688−0.05380.066*
C210.68940 (7)0.11232 (16)0.00738 (10)0.0498 (4)
C220.65199 (7)0.03749 (15)0.05197 (10)0.0455 (4)
H22A0.6660−0.03430.07340.055*
C230.59353 (6)0.07106 (13)0.06414 (9)0.0375 (3)
C240.75341 (8)0.0795 (2)−0.00596 (13)0.0688 (5)
H24A0.76160.00460.02070.103*
H24B0.77820.14050.01730.103*
H24C0.76110.0727−0.06440.103*
U11U22U33U12U13U23
S10.0411 (2)0.03568 (19)0.0451 (2)−0.00003 (15)0.00495 (16)0.00259 (15)
N10.0411 (7)0.0400 (7)0.0372 (7)−0.0024 (5)0.0005 (5)0.0015 (5)
N20.0386 (7)0.0320 (6)0.0519 (8)−0.0002 (5)0.0072 (6)0.0028 (5)
N30.0376 (6)0.0334 (6)0.0435 (8)−0.0027 (5)0.0044 (5)−0.0023 (5)
O10.0692 (8)0.0499 (7)0.0575 (8)0.0019 (6)−0.0072 (6)−0.0192 (6)
C10.0370 (7)0.0434 (8)0.0585 (11)−0.0011 (6)−0.0023 (7)−0.0003 (7)
C20.0336 (8)0.0619 (11)0.0631 (12)−0.0049 (7)0.0055 (7)−0.0002 (9)
C30.0483 (9)0.0560 (10)0.0568 (11)−0.0135 (8)0.0059 (8)0.0069 (8)
C40.0527 (10)0.0435 (9)0.0642 (12)−0.0015 (7)0.0048 (8)0.0091 (8)
C50.0399 (8)0.0400 (8)0.0551 (10)0.0008 (6)0.0041 (7)−0.0010 (7)
C60.0353 (7)0.0369 (7)0.0411 (9)−0.0048 (6)−0.0001 (6)−0.0053 (6)
C70.0359 (7)0.0348 (7)0.0423 (9)−0.0030 (6)−0.0017 (6)−0.0057 (6)
C80.0356 (7)0.0377 (8)0.0548 (10)−0.0020 (6)−0.0040 (7)−0.0013 (7)
C90.0388 (7)0.0360 (7)0.0405 (8)0.0002 (6)−0.0031 (6)0.0009 (6)
C100.0311 (7)0.0339 (7)0.0369 (8)0.0001 (5)−0.0003 (6)0.0027 (6)
C110.0536 (9)0.0375 (8)0.0358 (8)0.0010 (6)−0.0030 (7)0.0059 (6)
C120.0623 (10)0.0324 (7)0.0465 (10)0.0029 (7)0.0002 (8)0.0036 (6)
C130.0337 (7)0.0419 (8)0.0434 (9)0.0010 (6)0.0013 (6)−0.0056 (7)
C140.0370 (7)0.0487 (8)0.0374 (8)0.0031 (6)−0.0052 (6)0.0008 (6)
C150.0399 (8)0.0372 (7)0.0425 (9)0.0025 (6)−0.0052 (6)0.0062 (6)
C160.0759 (14)0.0946 (16)0.0600 (13)0.0059 (12)−0.0087 (11)−0.0341 (12)
C170.0376 (7)0.0346 (7)0.0322 (8)−0.0022 (6)−0.0009 (6)−0.0048 (6)
C180.0409 (8)0.0436 (8)0.0319 (8)−0.0050 (6)0.0007 (6)−0.0028 (6)
C190.0548 (10)0.0510 (10)0.0466 (10)−0.0072 (7)0.0057 (8)0.0075 (8)
C200.0513 (10)0.0659 (11)0.0477 (10)−0.0166 (8)0.0107 (8)0.0010 (8)
C210.0401 (8)0.0671 (11)0.0422 (9)−0.0069 (8)0.0043 (7)−0.0114 (8)
C220.0420 (8)0.0516 (9)0.0429 (9)0.0011 (7)0.0006 (7)−0.0048 (7)
C230.0399 (7)0.0413 (8)0.0314 (8)−0.0042 (6)0.0021 (6)−0.0019 (6)
C240.0437 (9)0.0941 (15)0.0686 (13)−0.0049 (10)0.0110 (9)−0.0166 (11)
S1—C231.7473 (15)C9—H9A0.9800
S1—C171.7534 (15)C10—C151.382 (2)
N1—C171.3042 (18)C10—C111.3891 (19)
N1—C181.3884 (19)C11—C121.380 (2)
N2—C171.3525 (18)C11—H11A0.9300
N2—N31.3824 (16)C12—C131.384 (2)
N2—C91.4780 (18)C12—H12A0.9300
N3—C71.2909 (18)C13—C141.379 (2)
O1—C131.3701 (17)C14—C151.386 (2)
O1—C161.410 (2)C14—H14A0.9300
C1—C21.389 (2)C15—H15A0.9300
C1—C61.390 (2)C16—H16A0.9600
C1—H1A0.9300C16—H16B0.9600
C2—C31.372 (2)C16—H16C0.9600
C2—H2A0.9300C18—C191.394 (2)
C3—C41.383 (2)C18—C231.400 (2)
C3—H3A0.9300C19—C201.381 (2)
C4—C51.379 (2)C19—H19A0.9300
C4—H4A0.9300C20—C211.390 (3)
C5—C61.400 (2)C20—H20A0.9300
C5—H5A0.9300C21—C221.391 (2)
C6—C71.462 (2)C21—C241.510 (2)
C7—C81.507 (2)C22—C231.389 (2)
C8—C91.541 (2)C22—H22A0.9300
C8—H8A0.9700C24—H24A0.9600
C8—H8B0.9700C24—H24B0.9600
C9—C101.513 (2)C24—H24C0.9600
C23—S1—C1787.93 (7)C11—C12—C13120.11 (14)
C17—N1—C18108.92 (12)C11—C12—H12A119.9
C17—N2—N3120.09 (11)C13—C12—H12A119.9
C17—N2—C9125.85 (12)O1—C13—C14124.69 (14)
N3—N2—C9113.76 (11)O1—C13—C12115.62 (13)
C7—N3—N2107.63 (12)C14—C13—C12119.69 (13)
C13—O1—C16118.20 (14)C13—C14—C15119.58 (14)
C2—C1—C6120.55 (15)C13—C14—H14A120.2
C2—C1—H1A119.7C15—C14—H14A120.2
C6—C1—H1A119.7C10—C15—C14121.61 (13)
C3—C2—C1120.21 (15)C10—C15—H15A119.2
C3—C2—H2A119.9C14—C15—H15A119.2
C1—C2—H2A119.9O1—C16—H16A109.5
C2—C3—C4119.85 (15)O1—C16—H16B109.5
C2—C3—H3A120.1H16A—C16—H16B109.5
C4—C3—H3A120.1O1—C16—H16C109.5
C5—C4—C3120.58 (16)H16A—C16—H16C109.5
C5—C4—H4A119.7H16B—C16—H16C109.5
C3—C4—H4A119.7N1—C17—N2122.78 (13)
C4—C5—C6120.16 (15)N1—C17—S1117.53 (11)
C4—C5—H5A119.9N2—C17—S1119.69 (10)
C6—C5—H5A119.9N1—C18—C19124.98 (14)
C1—C6—C5118.64 (14)N1—C18—C23116.23 (13)
C1—C6—C7120.11 (14)C19—C18—C23118.78 (14)
C5—C6—C7121.25 (13)C20—C19—C18119.07 (16)
N3—C7—C6121.56 (13)C20—C19—H19A120.5
N3—C7—C8113.48 (13)C18—C19—H19A120.5
C6—C7—C8124.96 (13)C19—C20—C21122.44 (15)
C7—C8—C9102.69 (12)C19—C20—H20A118.8
C7—C8—H8A111.2C21—C20—H20A118.8
C9—C8—H8A111.2C20—C21—C22118.73 (15)
C7—C8—H8B111.2C20—C21—C24120.51 (16)
C9—C8—H8B111.2C22—C21—C24120.74 (17)
H8A—C8—H8B109.1C23—C22—C21119.32 (16)
N2—C9—C10112.80 (12)C23—C22—H22A120.3
N2—C9—C899.91 (11)C21—C22—H22A120.3
C10—C9—C8112.79 (12)C22—C23—C18121.65 (14)
N2—C9—H9A110.3C22—C23—S1128.96 (12)
C10—C9—H9A110.3C18—C23—S1109.38 (11)
C8—C9—H9A110.3C21—C24—H24A109.5
C15—C10—C11117.93 (13)C21—C24—H24B109.5
C15—C10—C9121.45 (12)H24A—C24—H24B109.5
C11—C10—C9120.50 (13)C21—C24—H24C109.5
C12—C11—C10121.07 (15)H24A—C24—H24C109.5
C12—C11—H11A119.5H24B—C24—H24C109.5
C10—C11—H11A119.5
C17—N2—N3—C7−177.07 (13)C11—C12—C13—O1178.73 (15)
C9—N2—N3—C78.82 (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—C40.5 (3)C12—C13—C14—C150.6 (2)
C2—C3—C4—C5−0.2 (3)C11—C10—C15—C14−0.5 (2)
C3—C4—C5—C60.1 (3)C9—C10—C15—C14−176.56 (13)
C2—C1—C6—C50.6 (2)C13—C14—C15—C100.1 (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—S10.64 (16)
C4—C5—C6—C7179.05 (15)N3—N2—C17—N1179.42 (13)
N2—N3—C7—C6−177.70 (13)C9—N2—C17—N1−7.2 (2)
N2—N3—C7—C82.31 (17)N3—N2—C17—S1−0.46 (18)
C1—C6—C7—N3176.59 (15)C9—N2—C17—S1172.88 (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—N2179.61 (12)
C5—C6—C7—C8177.19 (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—C9168.52 (13)N1—C18—C19—C20179.20 (15)
C17—N2—C9—C10−68.81 (19)C23—C18—C19—C200.3 (2)
N3—N2—C9—C10104.90 (14)C18—C19—C20—C21−0.9 (3)
C17—N2—C9—C8171.19 (14)C19—C20—C21—C220.6 (3)
N3—N2—C9—C8−15.11 (16)C19—C20—C21—C24−178.27 (17)
C7—C8—C9—N214.51 (15)C20—C21—C22—C230.2 (2)
C7—C8—C9—C10−105.50 (14)C24—C21—C22—C23179.10 (15)
N2—C9—C10—C15−42.67 (19)C21—C22—C23—C18−0.8 (2)
C8—C9—C10—C1569.62 (17)C21—C22—C23—S1−179.64 (12)
N2—C9—C10—C11141.35 (14)N1—C18—C23—C22−178.48 (13)
C8—C9—C10—C11−106.37 (16)C19—C18—C23—C220.5 (2)
C15—C10—C11—C120.2 (2)N1—C18—C23—S10.60 (16)
C9—C10—C11—C12176.33 (14)C19—C18—C23—S1179.55 (12)
C10—C11—C12—C130.5 (2)C17—S1—C23—C22178.81 (15)
C16—O1—C13—C14−6.9 (2)C17—S1—C23—C18−0.18 (11)
C16—O1—C13—C12173.59 (16)
Cg1, Cg2 and Cg3 are the centroids of the S1/C17/N1/C18/C23, C1–C6 and C10–C15 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C15—H15A···Cg1i0.932.913.6318 (17)138
C22—H22A···Cg2i0.932.893.6438 (18)140
C2—H2A···Cg3ii0.932.743.4884 (18)138
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⋯AD—HH⋯AD⋯AD—H⋯A
C15—H15A⋯Cg1i0.932.913.6318 (17)138
C22—H22A⋯Cg2i0.932.893.6438 (18)140
C2—H2A⋯Cg3ii0.932.743.4884 (18)138

Symmetry codes: (i) ; (ii) .

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1.  A short history of SHELX.

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Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

2.  Synthesis and antidepressant activity of some 1,3,5-triphenyl-2-pyrazolines and 3-(2''-hydroxy naphthalen-1''-yl)-1,5-diphenyl-2-pyrazolines.

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Journal:  Bioorg Med Chem Lett       Date:  2005-11-15       Impact factor: 2.823

3.  Structure validation in chemical crystallography.

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  3 in total
  3 in total

1.  1-(6-Chloro-1,3-benzothia-zol-2-yl)hydrazine.

Authors:  Hoong-Kun Fun; Chin Wei Ooi; B K Sarojini; B J Mohan; B Narayana
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-02-17

2.  1-(6-Fluoro-1,3-benzothia-zol-2-yl)-3-phenyl-1H-pyrazole-4-carbaldehyde.

Authors:  Hoong-Kun Fun; Chin Wei Ooi; D Munirajasekhar; M Himaja; B K Sarojini
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-11-30

3.  2-[5-(4-Fluoro-phen-yl)-3-(4-methyl-phen-yl)-4,5-dihydro-1H-pyrazol-1-yl]-4-phenyl-1,3-thia-zole.

Authors:  Bakr F Abdel-Wahab; Hanan A Mohamed; Seik Weng Ng; Edward R T Tiekink
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2013-02-16
  3 in total

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