1,5-Dimethyl-4-(1-methyl-3-oxo-3-phenylprop-1-enyl­amino)-2-phenyl-1H-pyrazol-3(2H)-one

Zhu, H.; Wang, Z.; Ren, J.; Zhang, M.; Xu, W.

doi:10.1107/S1600536811021945

organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1640

doi:10.1107/S1600536811021945

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1,5-Dimethyl-4-(1-methyl-3-oxo-3-phenylprop-1-enylamino)-2-phenyl-1H-pyrazol-3(2H)-one

Hualing Zhu,^a ^* Zhan Wang,^a Junjie Ren,^a Miao Zhang ^a and Wei Xu ^a

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

(Received 22 May 2011; accepted 7 June 2011; online 11 June 2011)

In the title compound, C₂₁H₂₁N₃O₂, an intramolecular N—H⋯O interaction generates an S(6) ring, which stablizes the enamine–keto tautomer. The S(6) ring makes dihedral angles of 33.07 (7), 56.50 (8) and 38.59 (8)°, respectively, with the benzoylacetone benzene ring and the antipyrine pyrazole and benzene rings.

Related literature

For the antibacterial activity of Schiff bases, see: Zhang et al. (2008 ); Li et al. (2000 ). For general background to antipyrine, see: Filho et al. (1998 ); Bondock et al.(2008 ). For applications of 4-amino antipyrine Schiff bases, see: Meffin et al. (1977 ); Omar et al. (2006 ). For Schiff bases derived from aldehyde and 4-aminoantipyrine, see: Hay (2007 ); Raman et al. (2007 ). For our previous work on antipyrine Schiff bases, see: Zhu et al. (2011 ). For a related structure, see: Goh et al. (2009 ).

Experimental

Crystal data

C₂₁H₂₁N₃O₂
M_r = 347.41
Monoclinic, P 2₁ /c
a = 9.9418 (12) Å
b = 18.456 (3) Å
c = 10.1151 (14) Å
β = 104.361 (2)°
V = 1798.0 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 113 K
0.20 × 0.18 × 0.14 mm

Data collection

Rigaku Saturn724 CCD diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2001 ) T_min = 0.983, T_max = 0.988
18576 measured reflections
3160 independent reflections
2910 reflections with I > 2σ(I)
R_int = 0.061

Refinement

R[F² > 2σ(F²)] = 0.069
wR(F²) = 0.180
S = 1.11
3160 reflections
242 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯O2	0.90 (1)	1.81 (2)	2.591 (3)	143 (3)

Data collection: CrystalClear (Rigaku, 2001); 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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: CrystalStructure (Rigaku, 2001).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811021945/jh2294sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811021945/jh2294Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811021945/jh2294Isup3.cml

checkCIF report

Comment top

4-amino antipyrine derivatives have been widely used in the analgesic, anti-bacterial and antitumor field and chemical analysis (Filho et al., 1998; Bondock et al., 2008). While 4-amino antipyrine Schiff bases have showed unique properties and application in the biological, clinical, pharmaceutical and analytical fields (Omar et al., 2006; Meffin et al., 1977). In recent years, more studies concern for the Schiff bases derived from aldehyde and 4-aminoantipyrine (Raman et al., 2007; Hay, 2007), while less concern for the compound derived from ketone and 4-aminoantiprine. In continuation of our studies on antipyrine schiff bases (Zhu et al., 2011), we herein report the crystal structure of the title 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 C14 C15), which stablizing the enamine–keto form of the compound. The S(6) ring makes dihedral angles of 33.07 (7)°,56.55 (8)° and 38.59 (8)° with the benzene ring of benzoylacetone, 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).

Related literature top

For the antibacterial activity of Schiff bases, see: Zhang et al. (2008); Li et al. (2000). For general background to antipyrine, see: Filho et al. (1998); Bondock et al.(2008). For applications of 4-amino antipyrine Schiff bases, see: Meffin et al. (1977); Omar et al. (2006). For Schiff bases derived from aldehyde and 4-aminoantipyrine, see: Hay (2007); Raman et al. (2007). For our previous work on antipyrine Schiff bases, see: Zhu et al. (2011). For a related structure, see: Goh et al. (2009).

Experimental top

The title compound was synthesized by refluxing the mixture of benzoylacetone(15m mol) and 4-antipyrine (15m mol) in ethanol (100 ml) over a steam bath for about 7 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, 2001); cell refinement: CrystalClear (Rigaku, 2001); data reduction: CrystalClear (Rigaku, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: CrystalStructure (Rigaku, 2001).

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.

1,5-Dimethyl-4-(1-methyl-3-oxo-3-phenylprop-1-enylamino)-2-phenyl-1H- pyrazol-3(2H)-one top

Crystal data top

C₂₁H₂₁N₃O₂	F(000) = 736
M_r = 347.41	D_x = 1.283 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.9418 (12) Å	Cell parameters from 6064 reflections
b = 18.456 (3) Å	θ = 2.1–28.2°
c = 10.1151 (14) Å	µ = 0.08 mm⁻¹
β = 104.361 (2)°	T = 113 K
V = 1798.0 (4) Å³	Prism, colorless
Z = 4	0.20 × 0.18 × 0.14 mm

Data collection top

Rigaku Saturn724 CCD diffractometer	3160 independent reflections
Radiation source: rotating anode	2910 reflections with I > 2σ(I)
Multilayer monochromator	R_int = 0.061
Detector resolution: 14.22 pixels mm^-1	θ_max = 25.0°, θ_min = 2.1°
ω and ϕ scans	h = −11→11
Absorption correction: multi-scan (CrystalClear; Rigaku, 2001)	k = −21→21
T_min = 0.983, T_max = 0.988	l = −12→12
18576 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)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.180	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ²(F_o²) + (0.0849P)² + 1.0899P] where P = (F_o² + 2F_c²)/3
3160 reflections	(Δ/σ)_max < 0.001
242 parameters	Δρ_max = 0.20 e Å⁻³
1 restraint	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₂₁H₂₁N₃O₂	V = 1798.0 (4) Å³
M_r = 347.41	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.9418 (12) Å	µ = 0.08 mm⁻¹
b = 18.456 (3) Å	T = 113 K
c = 10.1151 (14) Å	0.20 × 0.18 × 0.14 mm
β = 104.361 (2)°

Data collection top

Rigaku Saturn724 CCD diffractometer	3160 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2001)	2910 reflections with I > 2σ(I)
T_min = 0.983, T_max = 0.988	R_int = 0.061
18576 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.069	1 restraint
wR(F²) = 0.180	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	Δρ_max = 0.20 e Å⁻³
3160 reflections	Δρ_min = −0.24 e Å⁻³
242 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
O1	0.72095 (18)	1.08766 (10)	0.41989 (19)	0.0284 (5)
O2	0.83461 (19)	0.93727 (10)	0.00431 (19)	0.0291 (5)
N1	0.4862 (2)	1.05874 (11)	0.3514 (2)	0.0249 (5)
N2	0.4038 (2)	1.01384 (12)	0.2496 (2)	0.0263 (5)
N3	0.7420 (2)	0.96481 (12)	0.2169 (2)	0.0268 (5)
C1	0.4275 (3)	1.12584 (14)	0.3815 (3)	0.0248 (6)
C2	0.4802 (3)	1.15799 (15)	0.5078 (3)	0.0287 (6)
H2	0.5552	1.1362	0.5722	0.034*
C3	0.4225 (3)	1.22220 (16)	0.5392 (3)	0.0337 (7)
H3A	0.4590	1.2448	0.6250	0.040*
C4	0.3118 (3)	1.25348 (15)	0.4457 (3)	0.0352 (7)
H4	0.2719	1.2972	0.4679	0.042*
C5	0.2596 (3)	1.22104 (15)	0.3202 (3)	0.0336 (7)
H5	0.1835	1.2426	0.2565	0.040*
C6	0.3173 (3)	1.15733 (14)	0.2864 (3)	0.0278 (6)
H6	0.2822	1.1355	0.1996	0.033*
C7	0.6269 (3)	1.04979 (14)	0.3528 (3)	0.0250 (6)
C8	0.6267 (3)	0.99043 (14)	0.2596 (3)	0.0258 (6)
C9	0.4928 (3)	0.97008 (14)	0.2037 (3)	0.0272 (6)
C10	0.4406 (3)	0.91013 (15)	0.1055 (3)	0.0344 (7)
H10A	0.4021	0.8716	0.1517	0.052*
H10B	0.5174	0.8907	0.0713	0.052*
H10C	0.3681	0.9287	0.0289	0.052*
C11	0.2724 (3)	0.98719 (15)	0.2733 (3)	0.0284 (6)
H11A	0.2200	0.9615	0.1919	0.043*
H11B	0.2176	1.0282	0.2923	0.043*
H11C	0.2920	0.9540	0.3514	0.043*
C12	0.8539 (3)	0.92975 (14)	0.2913 (3)	0.0251 (6)
C13	0.8703 (3)	0.92201 (16)	0.4421 (3)	0.0329 (7)
H13A	0.8720	0.9701	0.4834	0.049*
H13B	0.9573	0.8967	0.4827	0.049*
H13C	0.7921	0.8942	0.4586	0.049*
C14	0.9500 (3)	0.90044 (14)	0.2283 (3)	0.0260 (6)
H14	1.0305	0.8779	0.2833	0.031*
C15	0.9329 (3)	0.90276 (13)	0.0845 (3)	0.0241 (6)
C16	1.0308 (3)	0.86266 (13)	0.0208 (3)	0.0231 (6)
C17	1.0587 (3)	0.88942 (14)	−0.0988 (3)	0.0276 (6)
H17	1.0171	0.9334	−0.1373	0.033*
C18	1.1466 (3)	0.85217 (15)	−0.1615 (3)	0.0307 (6)
H18	1.1660	0.8708	−0.2423	0.037*
C19	1.2063 (3)	0.78773 (15)	−0.1065 (3)	0.0315 (7)
H19	1.2671	0.7625	−0.1495	0.038*
C20	1.1783 (3)	0.75975 (15)	0.0104 (3)	0.0340 (7)
H20	1.2187	0.7151	0.0470	0.041*
C21	1.0911 (3)	0.79702 (15)	0.0743 (3)	0.0302 (6)
H21	1.0720	0.7779	0.1549	0.036*
H3	0.739 (3)	0.9643 (18)	0.1269 (13)	0.046 (9)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0287 (10)	0.0262 (10)	0.0321 (11)	−0.0030 (8)	0.0107 (8)	−0.0034 (8)
O2	0.0313 (10)	0.0288 (10)	0.0290 (10)	0.0064 (8)	0.0107 (8)	0.0013 (8)
N1	0.0244 (11)	0.0230 (11)	0.0274 (12)	0.0019 (9)	0.0068 (9)	−0.0039 (9)
N2	0.0253 (11)	0.0255 (12)	0.0288 (12)	0.0008 (9)	0.0078 (9)	−0.0028 (9)
N3	0.0276 (12)	0.0285 (12)	0.0265 (12)	0.0038 (10)	0.0105 (10)	0.0011 (10)
C1	0.0270 (14)	0.0192 (13)	0.0326 (15)	0.0021 (10)	0.0158 (12)	0.0006 (11)
C2	0.0259 (14)	0.0302 (15)	0.0309 (15)	0.0011 (11)	0.0087 (12)	−0.0048 (12)
C3	0.0321 (15)	0.0335 (16)	0.0380 (17)	−0.0029 (12)	0.0136 (13)	−0.0089 (13)
C4	0.0361 (17)	0.0240 (14)	0.0487 (19)	0.0034 (12)	0.0167 (14)	−0.0051 (13)
C5	0.0345 (16)	0.0280 (15)	0.0411 (17)	0.0083 (12)	0.0146 (13)	0.0072 (13)
C6	0.0318 (15)	0.0261 (14)	0.0276 (14)	0.0019 (11)	0.0113 (12)	0.0021 (11)
C7	0.0261 (14)	0.0251 (14)	0.0269 (14)	0.0021 (11)	0.0123 (11)	0.0038 (11)
C8	0.0320 (15)	0.0248 (14)	0.0233 (14)	0.0019 (11)	0.0123 (12)	0.0020 (11)
C9	0.0322 (15)	0.0243 (14)	0.0258 (14)	0.0045 (11)	0.0084 (12)	0.0010 (11)
C10	0.0371 (16)	0.0311 (16)	0.0349 (16)	−0.0001 (12)	0.0085 (13)	−0.0100 (13)
C11	0.0237 (14)	0.0307 (15)	0.0317 (15)	−0.0005 (11)	0.0086 (11)	0.0029 (12)
C12	0.0269 (14)	0.0210 (13)	0.0292 (14)	−0.0009 (11)	0.0102 (11)	−0.0022 (11)
C13	0.0348 (16)	0.0391 (16)	0.0267 (15)	0.0043 (13)	0.0112 (13)	0.0003 (12)
C14	0.0247 (14)	0.0277 (14)	0.0260 (14)	0.0011 (11)	0.0068 (11)	0.0030 (11)
C15	0.0237 (13)	0.0198 (13)	0.0304 (14)	−0.0016 (10)	0.0095 (11)	−0.0011 (11)
C16	0.0222 (13)	0.0220 (13)	0.0249 (14)	0.0005 (10)	0.0053 (10)	−0.0022 (10)
C17	0.0272 (14)	0.0243 (14)	0.0306 (15)	−0.0014 (11)	0.0058 (11)	−0.0007 (11)
C18	0.0285 (15)	0.0377 (16)	0.0282 (15)	−0.0047 (12)	0.0116 (12)	−0.0060 (12)
C19	0.0275 (15)	0.0324 (15)	0.0352 (16)	0.0028 (12)	0.0089 (12)	−0.0087 (13)
C20	0.0344 (16)	0.0284 (15)	0.0404 (17)	0.0090 (12)	0.0117 (13)	0.0008 (13)
C21	0.0350 (15)	0.0258 (14)	0.0326 (15)	0.0028 (12)	0.0135 (12)	0.0031 (12)

Geometric parameters (Å, º) top

O1—C7	1.228 (3)	C10—H10B	0.9800
O2—C15	1.275 (3)	C10—H10C	0.9800
N1—C7	1.405 (3)	C11—H11A	0.9800
N1—N2	1.414 (3)	C11—H11B	0.9800
N1—C1	1.434 (3)	C11—H11C	0.9800
N2—C9	1.362 (3)	C12—C14	1.383 (4)
N2—C11	1.470 (3)	C12—C13	1.500 (4)
N3—C12	1.344 (3)	C13—H13A	0.9800
N3—C8	1.404 (3)	C13—H13B	0.9800
N3—H3	0.903 (10)	C13—H13C	0.9800
C1—C2	1.387 (4)	C14—C15	1.423 (4)
C1—C6	1.394 (4)	C14—H14	0.9500
C2—C3	1.387 (4)	C15—C16	1.490 (3)
C2—H2	0.9500	C16—C17	1.397 (4)
C3—C4	1.387 (4)	C16—C21	1.399 (4)
C3—H3A	0.9500	C17—C18	1.383 (4)
C4—C5	1.384 (4)	C17—H17	0.9500
C4—H4	0.9500	C18—C19	1.383 (4)
C5—C6	1.388 (4)	C18—H18	0.9500
C5—H5	0.9500	C19—C20	1.380 (4)
C6—H6	0.9500	C19—H19	0.9500
C7—C8	1.445 (4)	C20—C21	1.386 (4)
C8—C9	1.364 (4)	C20—H20	0.9500
C9—C10	1.492 (4)	C21—H21	0.9500
C10—H10A	0.9800

C7—N1—N2	109.5 (2)	H10B—C10—H10C	109.5
C7—N1—C1	123.8 (2)	N2—C11—H11A	109.5
N2—N1—C1	117.9 (2)	N2—C11—H11B	109.5
C9—N2—N1	106.7 (2)	H11A—C11—H11B	109.5
C9—N2—C11	122.4 (2)	N2—C11—H11C	109.5
N1—N2—C11	117.1 (2)	H11A—C11—H11C	109.5
C12—N3—C8	128.0 (2)	H11B—C11—H11C	109.5
C12—N3—H3	112 (2)	N3—C12—C14	120.0 (2)
C8—N3—H3	119 (2)	N3—C12—C13	118.8 (2)
C2—C1—C6	120.7 (2)	C14—C12—C13	121.2 (2)
C2—C1—N1	119.0 (2)	C12—C13—H13A	109.5
C6—C1—N1	120.3 (2)	C12—C13—H13B	109.5
C1—C2—C3	119.6 (3)	H13A—C13—H13B	109.5
C1—C2—H2	120.2	C12—C13—H13C	109.5
C3—C2—H2	120.2	H13A—C13—H13C	109.5
C4—C3—C2	120.2 (3)	H13B—C13—H13C	109.5
C4—C3—H3A	119.9	C12—C14—C15	122.6 (2)
C2—C3—H3A	119.9	C12—C14—H14	118.7
C5—C4—C3	120.0 (3)	C15—C14—H14	118.7
C5—C4—H4	120.0	O2—C15—C14	122.9 (2)
C3—C4—H4	120.0	O2—C15—C16	116.9 (2)
C4—C5—C6	120.6 (3)	C14—C15—C16	120.1 (2)
C4—C5—H5	119.7	C17—C16—C21	118.9 (2)
C6—C5—H5	119.7	C17—C16—C15	119.3 (2)
C5—C6—C1	119.0 (3)	C21—C16—C15	121.7 (2)
C5—C6—H6	120.5	C18—C17—C16	120.3 (3)
C1—C6—H6	120.5	C18—C17—H17	119.8
O1—C7—N1	124.0 (2)	C16—C17—H17	119.8
O1—C7—C8	132.0 (2)	C19—C18—C17	120.0 (3)
N1—C7—C8	104.0 (2)	C19—C18—H18	120.0
C9—C8—N3	124.6 (2)	C17—C18—H18	120.0
C9—C8—C7	108.8 (2)	C20—C19—C18	120.6 (3)
N3—C8—C7	126.0 (2)	C20—C19—H19	119.7
N2—C9—C8	110.2 (2)	C18—C19—H19	119.7
N2—C9—C10	121.3 (2)	C19—C20—C21	119.7 (3)
C8—C9—C10	128.5 (2)	C19—C20—H20	120.1
C9—C10—H10A	109.5	C21—C20—H20	120.1
C9—C10—H10B	109.5	C20—C21—C16	120.5 (3)
H10A—C10—H10B	109.5	C20—C21—H21	119.8
C9—C10—H10C	109.5	C16—C21—H21	119.8
H10A—C10—H10C	109.5

C7—N1—N2—C9	8.9 (3)	N1—N2—C9—C8	−6.8 (3)
C1—N1—N2—C9	157.7 (2)	C11—N2—C9—C8	−145.8 (2)
C7—N1—N2—C11	150.4 (2)	N1—N2—C9—C10	173.5 (2)
C1—N1—N2—C11	−60.8 (3)	C11—N2—C9—C10	34.6 (4)
C7—N1—C1—C2	−58.8 (3)	N3—C8—C9—N2	−168.8 (2)
N2—N1—C1—C2	157.1 (2)	C7—C8—C9—N2	2.3 (3)
C7—N1—C1—C6	122.5 (3)	N3—C8—C9—C10	10.8 (5)
N2—N1—C1—C6	−21.6 (3)	C7—C8—C9—C10	−178.0 (3)
C6—C1—C2—C3	−0.1 (4)	C8—N3—C12—C14	171.9 (3)
N1—C1—C2—C3	−178.8 (2)	C8—N3—C12—C13	−6.8 (4)
C1—C2—C3—C4	0.8 (4)	N3—C12—C14—C15	−2.9 (4)
C2—C3—C4—C5	−0.7 (4)	C13—C12—C14—C15	175.8 (2)
C3—C4—C5—C6	−0.2 (4)	C12—C14—C15—O2	6.3 (4)
C4—C5—C6—C1	0.9 (4)	C12—C14—C15—C16	−172.6 (2)
C2—C1—C6—C5	−0.8 (4)	O2—C15—C16—C17	31.3 (3)
N1—C1—C6—C5	177.9 (2)	C14—C15—C16—C17	−149.8 (2)
N2—N1—C7—O1	171.5 (2)	O2—C15—C16—C21	−145.8 (3)
C1—N1—C7—O1	24.9 (4)	C14—C15—C16—C21	33.1 (4)
N2—N1—C7—C8	−7.3 (3)	C21—C16—C17—C18	−1.2 (4)
C1—N1—C7—C8	−153.9 (2)	C15—C16—C17—C18	−178.4 (2)
C12—N3—C8—C9	−121.4 (3)	C16—C17—C18—C19	0.6 (4)
C12—N3—C8—C7	69.0 (4)	C17—C18—C19—C20	0.4 (4)
O1—C7—C8—C9	−175.5 (3)	C18—C19—C20—C21	−0.8 (4)
N1—C7—C8—C9	3.1 (3)	C19—C20—C21—C16	0.2 (4)
O1—C7—C8—N3	−4.5 (5)	C17—C16—C21—C20	0.8 (4)
N1—C7—C8—N3	174.1 (2)	C15—C16—C21—C20	177.9 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O2	0.90 (1)	1.81 (2)	2.591 (3)	143 (3)

Experimental details

Crystal data
Chemical formula	C₂₁H₂₁N₃O₂
M_r	347.41
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	113
a, b, c (Å)	9.9418 (12), 18.456 (3), 10.1151 (14)
β (°)	104.361 (2)
V (Å³)	1798.0 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.20 × 0.18 × 0.14

Data collection
Diffractometer	Rigaku Saturn724 CCD diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2001)
T_min, T_max	0.983, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	18576, 3160, 2910
R_int	0.061
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.069, 0.180, 1.11
No. of reflections	3160
No. of parameters	242
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.24

Computer programs: CrystalClear (Rigaku, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), CrystalStructure (Rigaku, 2001).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O2	0.903 (10)	1.81 (2)	2.591 (3)	143 (3)

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).

References

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Volume 67| Part 7| July 2011| Page o1640

doi:10.1107/S1600536811021945

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

1,5-Di­methyl-4-(1-methyl-3-oxo-3-phenylprop-1-enyl­amino)-2-phenyl-1H-pyrazol-3(2H)-one

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

1,5-Dimethyl-4-(1-methyl-3-oxo-3-phenylprop-1-enylamino)-2-phenyl-1H-pyrazol-3(2H)-one