1,5-Dimethyl-4-{[(3-methyl-5-oxo-1-phenyl-4,5-dihydro-1H-pyrazol-4-yl­idene)(thio­phen-2-yl)meth­yl]amino}-2-phenyl-1H-pyrazol-3(2H)-one

Zhu, H.; Ban, L.; Zhang, P.; Zhao, X.; Ren, J.

doi:10.1107/S1600536811002467

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 2| February 2011| Pages o476-o477

doi:10.1107/S1600536811002467

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1,5-Dimethyl-4-{[(3-methyl-5-oxo-1-phenyl-4,5-dihydro-1H-pyrazol-4-ylidene)(thiophen-2-yl)methyl]amino}-2-phenyl-1H-pyrazol-3(2H)-one

Hualing Zhu,^a ^* Litong Ban,^b Pingping Zhang,^c Xinxin Zhao ^a and Junjie Ren ^a

^aDepartment of Basic Science, Tianjin Agricultural College, Tianjin Jinjing Road No. 22, Tianjin 300384, People's Republic of China, ^bDepartment of Agricultural Science, Tianjin Agricultural College, Tianjin Jinjing Road No. 22, Tianjin 300384, People's Republic of China, and ^cDepartment of Food Science, Tianjin Agricultural College, Tianjin Jinjing Road No. 22, Tianjin 300384, People's Republic of China
^*Correspondence e-mail: zhuhualing2004@126.com

(Received 10 January 2011; accepted 18 January 2011; online 22 January 2011)

In the title compound, C₂₆H₂₃N₅O₂S, an intramolecular N—H⋯O interaction generates an S(6) ring. The essentially planar S(6) and pyrazole rings [maximum deviations = −0.0270 (14) and 0.0195 (15) Å, respectively] are nearly coplanar, making a dihedral angle of 3.94 (6)°. The S(6) ring makes dihedral angles of 23.79 (6), 78.53 (6) and 67.91 (6)° with the pyrazolone ring, the pyrazole ring and the benzene ring of antipyrine, respectively. The structure exhibits a thienyl-ring flip disorder with occupancy factors in the ratio 0.82:0.18.

Related literature

For general background to pyrazolones, see: Casas et al. (2007 ). For the antibacterial activity of pyrazolone Schiff bases, see: Zhang et al. (2008 ); Li et al. (2000 ). For our previous work in this area, see: Zhu et al. (2010a ,b ). For related structures, see: Shi et al. (2005 ); Goh et al. (2009 ). For disordered thienyl rings, see: Crundwell et al. (2003 ).

Experimental

Crystal data

C₂₆H₂₃N₅O₂S
M_r = 469.55
Monoclinic, C 2/c
a = 27.098 (3) Å
b = 7.9045 (8) Å
c = 22.308 (2) Å
β = 99.011 (8)°
V = 4719.4 (9) Å³
Z = 8
Mo Kα radiation
μ = 0.17 mm⁻¹
T = 293 K
0.42 × 0.36 × 0.34 mm

Data collection

Rigaku Saturn diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2008 ) T_min = 0.932, T_max = 0.944
22080 measured reflections
5570 independent reflections
3806 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.144
S = 1.02
5570 reflections
322 parameters
22 restraints
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯O2	0.86	1.96	2.6631 (18)	138

Data collection: CrystalClear (Rigaku, 2008); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ) and ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811002467/dn2653sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811002467/dn2653Isup2.hkl

checkCIF report

Comment top

Pyrazolones form a very important class of heterocycles due to their properties and applications (Casas et al., 2007). Schiff-bases derived from 1-phenyl-3-methyl-4-acyl-5-pyrazolone have found extensive application in coordination chemistry (Shi et al., 2005)and in antibacterial activation (Zhang et al., 2008; Li et al., 2000). In continuation of our studies on pyrazolone schiff bases (Zhu et al., 2010a,b), we herein report the crystal structure of the title pyrazole compound.

The molecular structure of the title compound is shown in Fig. 1. An intramolecular N—H···O interaction generates a six- membered ring, producing an S(6) ring (O2 N3 C12 C17 C18), which stablizing the enamine–keto form of the compound. The S(6) ring and pyrazole ring (N4 N5 C17 C18 C19) are essentially planar,with the maximum deviations of -0.0270 (14) and 0.0195 (15) Å, respectively, at atoms C12 and C17.The two rings are coplanar to one another, as indicated by the dihedral angle formed between them of 3.94 (6)°. The S(6) ring makes dihedral angles of 23.79 (6)°,78.53 (6)° and 67.91 (6)° with the benzene ring of pyrazolone, the pyrazole ring and benzene ring of antipyrine,respectively. The bond lengths and angles agree well with those closely related pyrazole structures (Goh et al., 2009)

The structure exhibits a thienyl-ring flip disorder with the occupancy factors in the ratio 82/18.

Related literature top

For general background to pyrazolones, see: Casas et al. (2007). For the antibacterial activity of pyrazolone Schiff bases, see: Zhang et al. (2008); Li et al. (2000). For our previous work in this area, see: Zhu et al. (2010a,b). For related structures, see: Shi et al. (2005); Goh et al. (2009). For disordered thienyl rings, see: Crundwell et al. (2003).

Experimental top

The title compound was synthesized by refluxing the mixture of 1-phenyl-3-methyl-4-(2-thenoyl)pyrazolone-5 (HPMTP) (15m mol) and 4-antipyrine (15m mol) in ethanol (100 ml) over a steam bath for about 4 h, then the solution was cooled down to room temperature. After seven days, pale yellow block was obtained and dried in air. The product was recrystallized from ethanol which afforded pale yellow and acerate crystals suitable for X–ray analysis.

Computing details top

Data collection: CrystalClear (Rigaku, 2008); cell refinement: CrystalClear (Rigaku, 2008); data reduction: CrystalClear (Rigaku, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are presented as a small spheres of arbitrary radii. Only the major component of the disordered thienyl ring is represented for the sake of clarity.

1,5-Dimethyl-4-{[(3-methyl-5-oxo-1-phenyl-4,5-dihydro-1H-pyrazol-4- ylidene)(thiophen-2-yl)methyl]amino}-2-phenyl-1H-pyrazol- 3(2H)-one top

Crystal data top

C₂₆H₂₃N₅O₂S	F(000) = 1968
M_r = 469.55	D_x = 1.322 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: -C 2yc	Cell parameters from 5913 reflections
a = 27.098 (3) Å	θ = 2.6–27.9°
b = 7.9045 (8) Å	µ = 0.17 mm⁻¹
c = 22.308 (2) Å	T = 293 K
β = 99.011 (8)°	Prism, colourless
V = 4719.4 (9) Å³	0.42 × 0.36 × 0.34 mm
Z = 8

Data collection top

Rigaku Saturn diffractometer	5570 independent reflections
Radiation source: rotating anode	3806 reflections with I > 2σ(I)
Multilayer monochromator	R_int = 0.037
Detector resolution: 7.31 pixels mm^-1	θ_max = 27.9°, θ_min = 2.6°
ω scans	h = −35→35
Absorption correction: multi-scan (CrystalClear; Rigaku, 2008)	k = −10→8
T_min = 0.932, T_max = 0.944	l = −29→29
22080 measured reflections

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.144	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0825P)²] where P = (F_o² + 2F_c²)/3
5570 reflections	(Δ/σ)_max = 0.003
322 parameters	Δρ_max = 0.23 e Å⁻³
22 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₂₆H₂₃N₅O₂S	V = 4719.4 (9) Å³
M_r = 469.55	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 27.098 (3) Å	µ = 0.17 mm⁻¹
b = 7.9045 (8) Å	T = 293 K
c = 22.308 (2) Å	0.42 × 0.36 × 0.34 mm
β = 99.011 (8)°

Data collection top

Rigaku Saturn diffractometer	5570 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2008)	3806 reflections with I > 2σ(I)
T_min = 0.932, T_max = 0.944	R_int = 0.037
22080 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	22 restraints
wR(F²) = 0.144	H-atom parameters constrained
S = 1.02	Δρ_max = 0.23 e Å⁻³
5570 reflections	Δρ_min = −0.25 e Å⁻³
322 parameters

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.

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	Occ. (<1)
O1	0.25433 (4)	1.02510 (13)	0.08661 (6)	0.0607 (3)
O2	0.08792 (4)	0.72515 (16)	−0.01432 (5)	0.0574 (3)
N1	0.30507 (4)	0.78662 (15)	0.09168 (6)	0.0454 (3)
N2	0.29718 (5)	0.61104 (15)	0.09307 (6)	0.0453 (3)
N3	0.17055 (5)	0.75910 (17)	0.06681 (6)	0.0490 (3)
H3	0.1558	0.7573	0.0298	0.059*
N4	0.01707 (5)	0.77052 (16)	0.03130 (6)	0.0483 (3)
N5	0.00673 (5)	0.81903 (18)	0.08851 (7)	0.0531 (4)
C1	0.25902 (6)	0.87031 (19)	0.08467 (7)	0.0440 (4)
C2	0.22290 (5)	0.73667 (18)	0.07704 (7)	0.0418 (3)
C3	0.24689 (6)	0.58580 (18)	0.07935 (7)	0.0431 (3)
C4	0.22546 (7)	0.4148 (2)	0.06696 (9)	0.0652 (5)
H4A	0.1900	0.4190	0.0665	0.098*
H4B	0.2402	0.3383	0.0981	0.098*
H4C	0.2323	0.3762	0.0283	0.098*
C5	0.35010 (6)	0.8549 (2)	0.12487 (7)	0.0473 (4)
C6	0.36892 (6)	1.0029 (2)	0.10435 (8)	0.0560 (4)
H6	0.3523	1.0563	0.0698	0.067*
C7	0.41249 (7)	1.0712 (3)	0.13541 (11)	0.0717 (6)
H7	0.4250	1.1720	0.1223	0.086*
C8	0.43721 (8)	0.9902 (3)	0.18544 (12)	0.0836 (7)
H8	0.4667	1.0357	0.2060	0.100*
C9	0.41887 (8)	0.8425 (3)	0.20554 (10)	0.0843 (6)
H9	0.4363	0.7876	0.2392	0.101*
C10	0.37464 (7)	0.7747 (3)	0.17596 (9)	0.0655 (5)
H10	0.3616	0.6765	0.1903	0.079*
C11	0.33387 (7)	0.4992 (2)	0.07232 (9)	0.0628 (5)
H11A	0.3337	0.3918	0.0924	0.094*
H11B	0.3665	0.5489	0.0816	0.094*
H11C	0.3256	0.4832	0.0293	0.094*
C12	0.14164 (6)	0.78314 (18)	0.11001 (7)	0.0431 (4)
S1	0.16071 (3)	0.63681 (8)	0.22363 (3)	0.0702 (2)	0.82
C13	0.16636 (6)	0.79831 (19)	0.17339 (7)	0.0468 (4)	0.82
C14	0.19533 (11)	0.9188 (3)	0.20297 (12)	0.0704 (8)	0.82
H14	0.2031	1.0169	0.1834	0.085*	0.82
C15	0.21288 (18)	0.8917 (6)	0.26270 (14)	0.0765 (8)	0.82
H15	0.2330	0.9675	0.2874	0.092*	0.82
C16	0.19767 (14)	0.7430 (5)	0.28143 (13)	0.0709 (9)	0.82
H16	0.2060	0.7018	0.3208	0.085*	0.82
S1'	0.20046 (19)	0.9710 (5)	0.1965 (2)	0.0702 (2)	0.18
C13'	0.16636 (6)	0.79831 (19)	0.17339 (7)	0.0468 (4)	0.18
C14'	0.1637 (5)	0.6894 (16)	0.2181 (5)	0.0704 (8)	0.18
H14'	0.1463	0.5877	0.2123	0.085*	0.18
C15'	0.1879 (8)	0.738 (2)	0.2721 (6)	0.0765 (8)	0.18
H15'	0.1895	0.6745	0.3075	0.092*	0.18
C16'	0.2097 (7)	0.889 (2)	0.2692 (6)	0.0709 (9)	0.18
H16'	0.2278	0.9432	0.3025	0.085*	0.18
C17	0.06744 (5)	0.75638 (19)	0.03103 (7)	0.0449 (4)
C18	0.09039 (6)	0.78841 (18)	0.09237 (7)	0.0437 (4)
C19	0.04936 (6)	0.8289 (2)	0.12425 (8)	0.0504 (4)
C20	0.05032 (7)	0.8851 (3)	0.18855 (9)	0.0727 (6)
H20A	0.0181	0.9285	0.1934	0.109*
H20B	0.0750	0.9721	0.1982	0.109*
H20C	0.0585	0.7907	0.2153	0.109*
C21	−0.02273 (6)	0.75001 (19)	−0.01723 (7)	0.0468 (4)
C22	−0.01595 (7)	0.6573 (2)	−0.06807 (8)	0.0579 (4)
H22	0.0149	0.6082	−0.0706	0.069*
C23	−0.05544 (7)	0.6384 (2)	−0.11491 (9)	0.0648 (5)
H23	−0.0511	0.5759	−0.1490	0.078*
C24	−0.10124 (7)	0.7112 (2)	−0.11174 (9)	0.0650 (5)
H24	−0.1276	0.6986	−0.1436	0.078*
C25	−0.10744 (7)	0.8021 (2)	−0.06118 (9)	0.0618 (5)
H25	−0.1383	0.8510	−0.0588	0.074*
C26	−0.06879 (6)	0.8225 (2)	−0.01381 (9)	0.0540 (4)
H26	−0.0735	0.8844	0.0203	0.065*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0648 (7)	0.0375 (6)	0.0805 (9)	0.0072 (5)	0.0132 (6)	0.0016 (5)
O2	0.0493 (6)	0.0790 (8)	0.0465 (7)	0.0004 (6)	0.0160 (5)	−0.0109 (6)
N1	0.0438 (7)	0.0364 (7)	0.0564 (8)	0.0001 (5)	0.0095 (6)	−0.0004 (5)
N2	0.0477 (8)	0.0353 (7)	0.0541 (8)	0.0042 (5)	0.0122 (6)	−0.0015 (5)
N3	0.0451 (7)	0.0643 (8)	0.0390 (7)	0.0024 (6)	0.0108 (6)	−0.0003 (6)
N4	0.0422 (7)	0.0559 (8)	0.0494 (8)	−0.0021 (6)	0.0152 (6)	−0.0073 (6)
N5	0.0494 (8)	0.0609 (9)	0.0531 (8)	−0.0029 (6)	0.0206 (7)	−0.0073 (6)
C1	0.0466 (9)	0.0403 (8)	0.0462 (9)	0.0041 (7)	0.0108 (7)	0.0004 (6)
C2	0.0427 (8)	0.0444 (8)	0.0395 (8)	0.0028 (6)	0.0100 (6)	0.0004 (6)
C3	0.0506 (9)	0.0411 (8)	0.0393 (8)	−0.0014 (7)	0.0122 (7)	0.0008 (6)
C4	0.0727 (12)	0.0466 (10)	0.0756 (13)	−0.0091 (9)	0.0088 (10)	−0.0026 (8)
C5	0.0449 (9)	0.0492 (9)	0.0496 (9)	−0.0004 (7)	0.0132 (7)	−0.0053 (7)
C6	0.0548 (10)	0.0545 (10)	0.0615 (11)	−0.0064 (8)	0.0180 (8)	−0.0054 (8)
C7	0.0580 (12)	0.0731 (13)	0.0879 (15)	−0.0165 (10)	0.0234 (11)	−0.0217 (11)
C8	0.0542 (12)	0.1040 (18)	0.0905 (17)	−0.0113 (12)	0.0047 (12)	−0.0319 (14)
C9	0.0697 (14)	0.1072 (18)	0.0688 (14)	0.0025 (13)	−0.0116 (11)	−0.0062 (13)
C10	0.0655 (12)	0.0736 (13)	0.0562 (11)	−0.0005 (10)	0.0059 (9)	0.0044 (9)
C11	0.0650 (11)	0.0491 (10)	0.0797 (13)	0.0140 (8)	0.0277 (10)	−0.0015 (9)
C12	0.0502 (9)	0.0384 (8)	0.0426 (8)	−0.0014 (6)	0.0134 (7)	0.0004 (6)
S1	0.0933 (5)	0.0628 (5)	0.0532 (4)	−0.0107 (4)	0.0077 (3)	0.0143 (3)
C13	0.0493 (9)	0.0510 (9)	0.0418 (8)	0.0006 (7)	0.0129 (7)	−0.0007 (7)
C14	0.111 (2)	0.0564 (18)	0.0461 (14)	−0.0152 (16)	0.0183 (13)	0.0058 (12)
C15	0.0871 (19)	0.096 (2)	0.0469 (15)	−0.0203 (15)	0.0134 (14)	−0.0138 (14)
C16	0.079 (2)	0.093 (2)	0.0389 (14)	0.0077 (16)	0.0025 (13)	0.0086 (14)
S1'	0.0933 (5)	0.0628 (5)	0.0532 (4)	−0.0107 (4)	0.0077 (3)	0.0143 (3)
C13'	0.0493 (9)	0.0510 (9)	0.0418 (8)	0.0006 (7)	0.0129 (7)	−0.0007 (7)
C14'	0.111 (2)	0.0564 (18)	0.0461 (14)	−0.0152 (16)	0.0183 (13)	0.0058 (12)
C15'	0.0871 (19)	0.096 (2)	0.0469 (15)	−0.0203 (15)	0.0134 (14)	−0.0138 (14)
C16'	0.079 (2)	0.093 (2)	0.0389 (14)	0.0077 (16)	0.0025 (13)	0.0086 (14)
C17	0.0441 (9)	0.0447 (8)	0.0481 (9)	−0.0024 (7)	0.0144 (7)	−0.0034 (6)
C18	0.0440 (9)	0.0450 (8)	0.0447 (8)	−0.0030 (6)	0.0149 (7)	−0.0023 (6)
C19	0.0507 (10)	0.0533 (9)	0.0509 (9)	−0.0034 (7)	0.0197 (8)	−0.0041 (7)
C20	0.0693 (12)	0.0975 (16)	0.0566 (11)	0.0001 (10)	0.0262 (9)	−0.0158 (10)
C21	0.0442 (9)	0.0437 (8)	0.0537 (9)	−0.0050 (7)	0.0113 (7)	0.0004 (7)
C22	0.0509 (10)	0.0610 (11)	0.0621 (11)	0.0011 (8)	0.0097 (8)	−0.0105 (8)
C23	0.0668 (12)	0.0650 (12)	0.0613 (12)	−0.0039 (9)	0.0056 (9)	−0.0120 (9)
C24	0.0592 (11)	0.0631 (12)	0.0688 (12)	−0.0045 (9)	−0.0019 (9)	0.0008 (9)
C25	0.0492 (10)	0.0544 (11)	0.0810 (14)	0.0022 (8)	0.0077 (9)	0.0043 (9)
C26	0.0488 (10)	0.0487 (9)	0.0660 (11)	−0.0009 (7)	0.0138 (8)	−0.0033 (8)

Geometric parameters (Å, º) top

O1—C1	1.2316 (17)	C12—C18	1.384 (2)
O2—C17	1.2524 (16)	C12—C13	1.472 (2)
N1—C1	1.3994 (19)	S1—C13	1.7213 (16)
N1—N2	1.4054 (17)	S1—C16	1.722 (3)
N1—C5	1.430 (2)	C13—C14	1.340 (3)
N2—C3	1.3637 (19)	C14—C15	1.360 (4)
N2—C11	1.4590 (19)	C14—H14	0.9300
N3—C12	1.3471 (18)	C15—C16	1.335 (3)
N3—C2	1.412 (2)	C15—H15	0.9300
N3—H3	0.8600	C16—H16	0.9300
N4—C17	1.3703 (19)	S1'—C16'	1.728 (10)
N4—N5	1.4023 (17)	C14'—C15'	1.336 (8)
N4—C21	1.413 (2)	C14'—H14'	0.9300
N5—C19	1.299 (2)	C15'—C16'	1.336 (8)
C1—C2	1.432 (2)	C15'—H15'	0.9300
C2—C3	1.355 (2)	C16'—H16'	0.9300
C3—C4	1.480 (2)	C17—C18	1.434 (2)
C4—H4A	0.9600	C18—C19	1.446 (2)
C4—H4B	0.9600	C19—C20	1.498 (2)
C4—H4C	0.9600	C20—H20A	0.9600
C5—C10	1.380 (2)	C20—H20B	0.9600
C5—C6	1.383 (2)	C20—H20C	0.9600
C6—C7	1.382 (3)	C21—C26	1.386 (2)
C6—H6	0.9300	C21—C22	1.387 (2)
C7—C8	1.368 (3)	C22—C23	1.382 (3)
C7—H7	0.9300	C22—H22	0.9300
C8—C9	1.371 (3)	C23—C24	1.380 (3)
C8—H8	0.9300	C23—H23	0.9300
C9—C10	1.382 (3)	C24—C25	1.370 (3)
C9—H9	0.9300	C24—H24	0.9300
C10—H10	0.9300	C25—C26	1.376 (3)
C11—H11A	0.9600	C25—H25	0.9300
C11—H11B	0.9600	C26—H26	0.9300
C11—H11C	0.9600

C1—N1—N2	109.46 (11)	C18—C12—C13	123.81 (13)
C1—N1—C5	123.58 (12)	C13—S1—C16	91.47 (12)
N2—N1—C5	118.79 (12)	C14—C13—C12	132.40 (16)
C3—N2—N1	106.84 (11)	C14—C13—S1	108.14 (15)
C3—N2—C11	123.14 (13)	C12—C13—S1	119.45 (12)
N1—N2—C11	118.55 (12)	C13—C14—C15	117.3 (3)
C12—N3—C2	125.74 (14)	C13—C14—H14	121.3
C12—N3—H3	117.1	C15—C14—H14	121.3
C2—N3—H3	117.1	C16—C15—C14	111.6 (3)
C17—N4—N5	111.56 (13)	C16—C15—H15	124.2
C17—N4—C21	128.95 (13)	C14—C15—H15	124.2
N5—N4—C21	119.43 (12)	C15—C16—S1	111.5 (3)
C19—N5—N4	106.83 (12)	C15—C16—H16	124.2
O1—C1—N1	124.12 (14)	S1—C16—H16	124.2
O1—C1—C2	131.66 (14)	C15'—C14'—H14'	122.8
N1—C1—C2	104.21 (12)	C16'—C15'—C14'	111.7 (12)
C3—C2—N3	125.48 (14)	C16'—C15'—H15'	124.1
C3—C2—C1	109.25 (13)	C14'—C15'—H15'	124.1
N3—C2—C1	125.25 (13)	C15'—C16'—S1'	112.5 (11)
C2—C3—N2	109.66 (13)	C15'—C16'—H16'	123.7
C2—C3—C4	128.65 (15)	S1'—C16'—H16'	123.7
N2—C3—C4	121.65 (14)	O2—C17—N4	125.97 (15)
C3—C4—H4A	109.5	O2—C17—C18	128.66 (14)
C3—C4—H4B	109.5	N4—C17—C18	105.36 (12)
H4A—C4—H4B	109.5	C12—C18—C17	122.15 (13)
C3—C4—H4C	109.5	C12—C18—C19	132.96 (15)
H4A—C4—H4C	109.5	C17—C18—C19	104.85 (13)
H4B—C4—H4C	109.5	N5—C19—C18	111.29 (14)
C10—C5—C6	120.45 (17)	N5—C19—C20	119.07 (14)
C10—C5—N1	121.06 (15)	C18—C19—C20	129.57 (16)
C6—C5—N1	118.48 (15)	C19—C20—H20A	109.5
C7—C6—C5	119.67 (19)	C19—C20—H20B	109.5
C7—C6—H6	120.2	H20A—C20—H20B	109.5
C5—C6—H6	120.2	C19—C20—H20C	109.5
C8—C7—C6	119.8 (2)	H20A—C20—H20C	109.5
C8—C7—H7	120.1	H20B—C20—H20C	109.5
C6—C7—H7	120.1	C26—C21—C22	119.95 (16)
C7—C8—C9	120.6 (2)	C26—C21—N4	119.76 (15)
C7—C8—H8	119.7	C22—C21—N4	120.29 (14)
C9—C8—H8	119.7	C23—C22—C21	119.30 (16)
C8—C9—C10	120.4 (2)	C23—C22—H22	120.3
C8—C9—H9	119.8	C21—C22—H22	120.3
C10—C9—H9	119.8	C24—C23—C22	120.84 (18)
C5—C10—C9	119.1 (2)	C24—C23—H23	119.6
C5—C10—H10	120.5	C22—C23—H23	119.6
C9—C10—H10	120.5	C25—C24—C23	119.24 (18)
N2—C11—H11A	109.5	C25—C24—H24	120.4
N2—C11—H11B	109.5	C23—C24—H24	120.4
H11A—C11—H11B	109.5	C24—C25—C26	121.12 (17)
N2—C11—H11C	109.5	C24—C25—H25	119.4
H11A—C11—H11C	109.5	C26—C25—H25	119.4
H11B—C11—H11C	109.5	C25—C26—C21	119.55 (17)
N3—C12—C18	118.10 (14)	C25—C26—H26	120.2
N3—C12—C13	118.08 (14)	C21—C26—H26	120.2

C1—N1—N2—C3	7.51 (15)	N3—C12—C13—S1	−109.04 (14)
C5—N1—N2—C3	157.23 (12)	C18—C12—C13—S1	69.48 (18)
C1—N1—N2—C11	152.10 (15)	C16—S1—C13—C14	0.23 (16)
C5—N1—N2—C11	−58.19 (19)	C16—S1—C13—C12	179.22 (18)
C17—N4—N5—C19	−2.41 (18)	C12—C13—C14—C15	−179.3 (2)
C21—N4—N5—C19	−179.86 (14)	S1—C13—C14—C15	−0.51 (16)
N2—N1—C1—O1	174.18 (15)	C13—C14—C15—C16	0.6 (2)
C5—N1—C1—O1	26.2 (2)	C14—C15—C16—S1	−0.4 (2)
N2—N1—C1—C2	−4.47 (15)	C13—S1—C16—C15	0.1 (2)
C5—N1—C1—C2	−152.43 (14)	C14'—C15'—C16'—S1'	−1.0 (5)
C12—N3—C2—C3	97.57 (19)	N5—N4—C17—O2	−175.43 (15)
C12—N3—C2—C1	−84.5 (2)	C21—N4—C17—O2	1.7 (3)
O1—C1—C2—C3	−178.69 (17)	N5—N4—C17—C18	3.33 (16)
N1—C1—C2—C3	−0.18 (16)	C21—N4—C17—C18	−179.53 (14)
O1—C1—C2—N3	3.1 (3)	N3—C12—C18—C17	4.9 (2)
N1—C1—C2—N3	−178.36 (13)	C13—C12—C18—C17	−173.64 (14)
N3—C2—C3—N2	−176.91 (13)	N3—C12—C18—C19	−172.35 (16)
C1—C2—C3—N2	4.92 (17)	C13—C12—C18—C19	9.1 (3)
N3—C2—C3—C4	5.7 (3)	O2—C17—C18—C12	−2.1 (3)
C1—C2—C3—C4	−172.46 (16)	N4—C17—C18—C12	179.21 (14)
N1—N2—C3—C2	−7.60 (16)	O2—C17—C18—C19	175.83 (16)
C11—N2—C3—C2	−150.16 (14)	N4—C17—C18—C19	−2.88 (16)
N1—N2—C3—C4	170.00 (14)	N4—N5—C19—C18	0.41 (18)
C11—N2—C3—C4	27.4 (2)	N4—N5—C19—C20	177.69 (15)
C1—N1—C5—C10	117.51 (17)	C12—C18—C19—N5	179.15 (16)
N2—N1—C5—C10	−27.7 (2)	C17—C18—C19—N5	1.57 (18)
C1—N1—C5—C6	−63.0 (2)	C12—C18—C19—C20	2.2 (3)
N2—N1—C5—C6	151.78 (13)	C17—C18—C19—C20	−175.35 (18)
C10—C5—C6—C7	−0.2 (2)	C17—N4—C21—C26	−158.43 (15)
N1—C5—C6—C7	−179.70 (14)	N5—N4—C21—C26	18.5 (2)
C5—C6—C7—C8	1.3 (3)	C17—N4—C21—C22	21.8 (2)
C6—C7—C8—C9	−0.7 (3)	N5—N4—C21—C22	−161.24 (15)
C7—C8—C9—C10	−1.0 (3)	C26—C21—C22—C23	0.1 (3)
C6—C5—C10—C9	−1.4 (3)	N4—C21—C22—C23	179.81 (15)
N1—C5—C10—C9	178.03 (16)	C21—C22—C23—C24	0.3 (3)
C8—C9—C10—C5	2.0 (3)	C22—C23—C24—C25	−0.4 (3)
C2—N3—C12—C18	−174.54 (14)	C23—C24—C25—C26	0.2 (3)
C2—N3—C12—C13	4.1 (2)	C24—C25—C26—C21	0.1 (3)
N3—C12—C13—C14	69.7 (2)	C22—C21—C26—C25	−0.2 (2)
C18—C12—C13—C14	−111.8 (2)	N4—C21—C26—C25	−179.99 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O2	0.86	1.96	2.6631 (18)	138

Experimental details

Crystal data
Chemical formula	C₂₆H₂₃N₅O₂S
M_r	469.55
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	27.098 (3), 7.9045 (8), 22.308 (2)
β (°)	99.011 (8)
V (Å³)	4719.4 (9)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.17
Crystal size (mm)	0.42 × 0.36 × 0.34

Data collection
Diffractometer	Rigaku Saturn diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2008)
T_min, T_max	0.932, 0.944
No. of measured, independent and observed [I > 2σ(I)] reflections	22080, 5570, 3806
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.659

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.144, 1.02
No. of reflections	5570
No. of parameters	322
No. of restraints	22
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.25

Computer programs: CrystalClear (Rigaku, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O2	0.86	1.96	2.6631 (18)	138

Acknowledgements

The authors are grateful for financial support from the Spark Program Foundation of Science and Technology Department of China (research Nos. 09ZHXHNC07900 and 2010 GA610009). The authors also thank the Technical Staff Serving Enterprise Action Committee of the Science and Technology Department of China for financial support (research No. 2009 GJ A10022).

References

Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA. Google Scholar
Casas, J. S., Garcl'a-Tasende,M. S., Sanchez, A., Sordo, J. & Touceda, A. (2007). Coord. Chem. Rev. 251, 1561–1589. CrossRef CAS Google Scholar
Crundwell, G., Sullivan, J., Pelto, R. & Kantardjieff, K. (2003). J. Chem. Crystallogr. 33, 239–244. Web of Science CSD CrossRef CAS Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Goh, J. H., Fun, H.-K., Nithinchandra,, Rai, N. S. & Kalluraya, B. (2009). Acta Cryst. E65, o3099–o3100. Google Scholar
Li, J.-Z., Li, G. & Yu, W.-J. (2000). J. Rare Earth, 18, 233–236. Google Scholar
Rigaku (2008). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shi, J. M., Zhang, F. X., Wu, C. J. & Liu, L. D. (2005). Acta Cryst. E61, m2320–m2321. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zhang, H.-Q., Li, J.-Z., Zhang, Y. & Zhang, D. (2008). Chin. Inorg. Chem. 24, 990–993. Web of Science CSD CrossRef CAS Google Scholar
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Volume 67| Part 2| February 2011| Pages o476-o477

doi:10.1107/S1600536811002467

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

1,5-Di­methyl-4-{[(3-methyl-5-oxo-1-phenyl-4,5-di­hydro-1H-pyrazol-4-yl­­idene)(thio­phen-2-yl)meth­yl]amino}-2-phenyl-1H-pyrazol-3(2H)-one

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

1,5-Dimethyl-4-{[(3-methyl-5-oxo-1-phenyl-4,5-dihydro-1H-pyrazol-4-ylidene)(thiophen-2-yl)methyl]amino}-2-phenyl-1H-pyrazol-3(2H)-one