4-[(Z)-(n-Butyl­amino)(phenyl)methyl­idene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one

Wang, H.-W.

doi:10.1107/S1600536812009166

organic compounds

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ISSN: 2056-9890

Volume 68| Part 4| April 2012| Page o969

doi:10.1107/S1600536812009166

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4-[(Z)-(n-Butylamino)(phenyl)methylidene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one

Hai-Wen Wang ^a ^*

^aEast China University of Science and Technology, College of Chemistry and Molecular Engineering, Mei Long Road 130, Shanghai 200237, People's Republic of China
^*Correspondence e-mail: wanghaiwen@ecust.edu.cn

(Received 21 February 2012; accepted 1 March 2012; online 7 March 2012)

The title compound, C₂₁H₂₃N₃O, exists in an enamine–keto form with the amino group involved in an intramolecular N—H⋯O hydrogen bond. The dihedral angle between the phenyl rings is 73.59 (6)°. The five-membered ring is nearly planar, the largest deviation being 0.0004 (7) Å, and makes dihedral angles of 4.81 (6) and 69.81 (5)° wth the phenyl rings. In the crystal, pairs of weak C—H⋯O interactions link the molecules into centrosymmetric dimers.

Related literature

For applications of Schiff bases derived from 4-acylpyrazolones, see: Bernardino et al. (2006 ); Zhang et al. (2008 ). For related structures, see: Zhang et al. (2007 ); Chi et al. (2010 ); Zhen & Han (2005 ); Wang (2010 ).

Experimental

Crystal data

C₂₁H₂₃N₃O
M_r = 333.42
Monoclinic, P 2₁ /n
a = 9.5215 (9) Å
b = 14.7867 (14) Å
c = 12.8055 (12) Å
β = 100.645 (2)°
V = 1771.9 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 K
0.28 × 0.20 × 0.16 mm

Data collection

Bruker SMART 1000 CCD diffractometer
16506 measured reflections
4368 independent reflections
3362 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.103
S = 1.01
4368 reflections
232 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O1	0.921 (16)	1.873 (16)	2.6704 (14)	143.5 (14)
C13—H13⋯O1ⁱ	0.93	2.39	3.3175 (15)	172
Symmetry code: (i) -x+1, -y, -z+2.

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT-Plus (Bruker, 2003 ); data reduction: SAINT-Plus; 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812009166/cv5252sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812009166/cv5252Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812009166/cv5252Isup3.cml

checkCIF report

Comment top

The Schiff bases derived from 4-acylpyrazolones have attracted much attention due to their applications in pharmaceutical and agrochemical fields (e.g. Bernardino et al., 2006; Zhang et al., 2008). In order to expand this field, we now report the synthesis and structure of the title compound, (I) (Fig. 1).

In (I), the Schiff base molecule adopts an E geometry with respect to the C=N bond (Fig. 1). All bond lengths and angles are comparable with those found in the related compounds (Chi et al., 2010; Wang et al., 2010; Zhen et al., 2005; Zhang et al.., 2007). The dihedral angle between the two phenyl rings is 73.59 (6)°. The five-membered ring of the title compound is nearly planar, with the largest deviation being 0.0004 (7)%A for atom N1. The dihedral angles between this mean plane and two benzene rings are 4.81 (6)° and 69.81 (5)%. Weak intermolecular C—H···O interactions (Table 1) link the molecules into centrosymmetric dimers.

Related literature top

For applications of Schiff bases derived from 4-acylpyrazolones, see: Bernardino et al. (2006); Zhang et al. (2008). For related structures, see: Zhang et al. (2007); Chi et al. (2010); Zhen & Han (2005); Wang (2010).

Experimental top

A mixture of a 10 ml HPMBP (2 mmol, 0.5566 g) anhydrous ethanol solution, and a 0.2 ml n-butylamine (2 mmol, 0.1463 g) solution was refluxed for ca 8 h, with addition of a few drops of glacial acetic acid as a catalyst. The ethanol was removed by evaporation and the resulting green precipitate formed was filtered off, washed with cold anhydrous ethanol and dried in air. Yellow block single crystals suitable for analysis were obtained by slow evaporation of a solution in anhydrous ethanol at room temperature for a few days.

Structure description top

For applications of Schiff bases derived from 4-acylpyrazolones, see: Bernardino et al. (2006); Zhang et al. (2008). For related structures, see: Zhang et al. (2007); Chi et al. (2010); Zhen & Han (2005); Wang (2010).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2003); data reduction: SAINT-Plus (Bruker, 2003); 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).

Figures top

Fig. 1. The molecular structure of (I) showing the atomic numbering and 30% probability displacement ellipsoids. Dashed line denotes hydrogen bond.

4-[(Z)-(n-Butylamino)(phenyl)methylidene]-3-methyl- 1-phenyl-1H-pyrazol-5(4H)-one top

Crystal data top

C₂₁H₂₃N₃O	F(000) = 712.0
M_r = 333.42	D_x = 1.250 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3753 reflections
a = 9.5215 (9) Å	θ = 2.6–28.1°
b = 14.7867 (14) Å	µ = 0.08 mm⁻¹
c = 12.8055 (12) Å	T = 296 K
β = 100.645 (2)°	Block, yellow
V = 1771.9 (3) Å³	0.28 × 0.20 × 0.16 mm
Z = 4

Data collection top

Bruker SMART 1000 CCD diffractometer	3362 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.035
Graphite monochromator	θ_max = 28.3°, θ_min = 2.6°
phi and ω scans	h = −12→12
16506 measured reflections	k = −19→19
4368 independent reflections	l = −17→16

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.103	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.0499P)² + 0.4177P] where P = (F_o² + 2F_c²)/3
4368 reflections	(Δ/σ)_max < 0.001
232 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₂₁H₂₃N₃O	V = 1771.9 (3) Å³
M_r = 333.42	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.5215 (9) Å	µ = 0.08 mm⁻¹
b = 14.7867 (14) Å	T = 296 K
c = 12.8055 (12) Å	0.28 × 0.20 × 0.16 mm
β = 100.645 (2)°

Data collection top

Bruker SMART 1000 CCD diffractometer	3362 reflections with I > 2σ(I)
16506 measured reflections	R_int = 0.035
4368 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.103	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.30 e Å⁻³
4368 reflections	Δρ_min = −0.20 e Å⁻³
232 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
C1	0.21783 (12)	0.26068 (9)	0.88837 (9)	0.0167 (2)
C2	0.10538 (13)	0.21696 (9)	0.92399 (9)	0.0204 (3)
H2	0.1013	0.1541	0.9255	0.024*
C3	−0.00037 (13)	0.26856 (9)	0.95714 (10)	0.0218 (3)
H3	−0.0742	0.2397	0.9824	0.026*
C4	0.00239 (13)	0.36198 (9)	0.95320 (9)	0.0218 (3)
H4	−0.0699	0.3957	0.9744	0.026*
C5	0.11413 (13)	0.40483 (9)	0.91726 (10)	0.0220 (3)
H5	0.1166	0.4676	0.9144	0.026*
C6	0.22209 (13)	0.35488 (9)	0.88561 (9)	0.0193 (3)
H6	0.2973	0.3842	0.8626	0.023*
C7	0.35303 (12)	0.11883 (8)	0.85902 (9)	0.0158 (2)
C8	0.48777 (12)	0.10785 (8)	0.82441 (9)	0.0159 (2)
C9	0.53156 (12)	0.19778 (8)	0.80232 (9)	0.0168 (2)
C10	0.66208 (13)	0.22991 (9)	0.76371 (10)	0.0217 (3)
H10A	0.6553	0.2136	0.6904	0.033*
H10B	0.7453	0.2023	0.8052	0.033*
H10C	0.6693	0.2945	0.7708	0.033*
C11	0.55372 (12)	0.02287 (8)	0.82705 (9)	0.0152 (2)
C12	0.69661 (12)	0.00963 (8)	0.79819 (9)	0.0153 (2)
C13	0.81099 (13)	−0.01709 (9)	0.87666 (9)	0.0185 (3)
H13	0.7970	−0.0279	0.9456	0.022*
C14	0.94570 (13)	−0.02752 (9)	0.85151 (10)	0.0221 (3)
H14	1.0223	−0.0446	0.9038	0.027*
C15	0.96628 (13)	−0.01252 (9)	0.74855 (10)	0.0228 (3)
H15	1.0567	−0.0195	0.7319	0.027*
C16	0.85241 (14)	0.01285 (9)	0.67051 (10)	0.0212 (3)
H16	0.8663	0.0221	0.6013	0.025*
C17	0.71793 (13)	0.02451 (8)	0.69496 (9)	0.0179 (2)
H17	0.6419	0.0423	0.6425	0.021*
C18	0.53117 (13)	−0.14295 (8)	0.85933 (9)	0.0177 (2)
H18A	0.6204	−0.1519	0.9088	0.021*
H18B	0.5456	−0.1600	0.7889	0.021*
C19	0.41494 (13)	−0.20109 (8)	0.89147 (9)	0.0172 (2)
H19A	0.4043	−0.1852	0.9631	0.021*
H19B	0.3250	−0.1886	0.8444	0.021*
C20	0.44787 (13)	−0.30125 (9)	0.88723 (10)	0.0197 (3)
H20A	0.5401	−0.3132	0.9316	0.024*
H20B	0.4540	−0.3177	0.8149	0.024*
C21	0.33508 (15)	−0.35963 (9)	0.92449 (11)	0.0262 (3)
H21A	0.3317	−0.3456	0.9972	0.039*
H21B	0.3589	−0.4223	0.9188	0.039*
H21C	0.2435	−0.3478	0.8810	0.039*
H3A	0.4031 (17)	−0.0341 (11)	0.8798 (12)	0.030 (4)*
N1	0.32840 (10)	0.21097 (7)	0.85512 (8)	0.0172 (2)
N2	0.43854 (10)	0.25859 (7)	0.82022 (8)	0.0182 (2)
N3	0.48854 (11)	−0.04789 (7)	0.85966 (8)	0.0172 (2)
O1	0.27412 (9)	0.06007 (6)	0.88848 (7)	0.0195 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0156 (5)	0.0187 (6)	0.0152 (5)	0.0023 (5)	0.0014 (4)	−0.0004 (4)
C2	0.0197 (6)	0.0187 (6)	0.0231 (6)	0.0020 (5)	0.0050 (5)	0.0022 (5)
C3	0.0188 (6)	0.0255 (7)	0.0219 (6)	0.0013 (5)	0.0058 (5)	0.0014 (5)
C4	0.0203 (6)	0.0251 (7)	0.0204 (6)	0.0061 (5)	0.0048 (5)	−0.0026 (5)
C5	0.0249 (6)	0.0175 (7)	0.0234 (6)	0.0020 (5)	0.0042 (5)	−0.0032 (5)
C6	0.0189 (6)	0.0180 (6)	0.0209 (6)	−0.0008 (5)	0.0034 (4)	−0.0002 (5)
C7	0.0163 (5)	0.0158 (6)	0.0149 (5)	−0.0001 (5)	0.0019 (4)	0.0002 (4)
C8	0.0150 (5)	0.0171 (6)	0.0157 (5)	−0.0013 (4)	0.0034 (4)	0.0005 (4)
C9	0.0165 (5)	0.0171 (6)	0.0167 (5)	−0.0003 (5)	0.0026 (4)	0.0004 (4)
C10	0.0200 (6)	0.0174 (6)	0.0293 (6)	−0.0020 (5)	0.0088 (5)	0.0009 (5)
C11	0.0156 (5)	0.0171 (6)	0.0128 (5)	−0.0014 (5)	0.0019 (4)	0.0000 (4)
C12	0.0154 (5)	0.0129 (6)	0.0184 (5)	−0.0009 (4)	0.0050 (4)	−0.0011 (4)
C13	0.0184 (6)	0.0186 (6)	0.0188 (5)	−0.0011 (5)	0.0042 (4)	0.0005 (5)
C14	0.0162 (6)	0.0213 (7)	0.0282 (6)	−0.0001 (5)	0.0024 (5)	0.0004 (5)
C15	0.0170 (6)	0.0209 (7)	0.0333 (7)	−0.0030 (5)	0.0116 (5)	−0.0056 (5)
C16	0.0261 (6)	0.0189 (6)	0.0208 (6)	−0.0054 (5)	0.0106 (5)	−0.0040 (5)
C17	0.0197 (6)	0.0159 (6)	0.0183 (5)	−0.0023 (5)	0.0038 (4)	−0.0010 (5)
C18	0.0181 (5)	0.0142 (6)	0.0216 (5)	0.0010 (5)	0.0055 (4)	0.0006 (5)
C19	0.0181 (5)	0.0159 (6)	0.0182 (5)	−0.0007 (5)	0.0051 (4)	0.0012 (4)
C20	0.0218 (6)	0.0153 (6)	0.0224 (6)	−0.0006 (5)	0.0047 (5)	0.0012 (5)
C21	0.0324 (7)	0.0190 (7)	0.0283 (6)	−0.0056 (6)	0.0087 (5)	0.0008 (5)
N1	0.0159 (5)	0.0149 (5)	0.0218 (5)	0.0002 (4)	0.0064 (4)	0.0020 (4)
N2	0.0164 (5)	0.0168 (5)	0.0226 (5)	−0.0020 (4)	0.0068 (4)	0.0016 (4)
N3	0.0165 (5)	0.0142 (5)	0.0224 (5)	0.0007 (4)	0.0073 (4)	0.0009 (4)
O1	0.0180 (4)	0.0168 (5)	0.0252 (4)	−0.0018 (3)	0.0082 (3)	0.0018 (3)

Geometric parameters (Å, º) top

C1—C6	1.3942 (18)	C12—C13	1.3956 (16)
C1—C2	1.3975 (17)	C13—C14	1.3876 (17)
C1—N1	1.4125 (15)	C13—H13	0.9300
C2—C3	1.3906 (18)	C14—C15	1.3861 (18)
C2—H2	0.9300	C14—H14	0.9300
C3—C4	1.3827 (19)	C15—C16	1.3838 (18)
C3—H3	0.9300	C15—H15	0.9300
C4—C5	1.3879 (19)	C16—C17	1.3840 (17)
C4—H4	0.9300	C16—H16	0.9300
C5—C6	1.3858 (18)	C17—H17	0.9300
C5—H5	0.9300	C18—N3	1.4633 (16)
C6—H6	0.9300	C18—C19	1.5171 (16)
C7—O1	1.2516 (15)	C18—H18A	0.9700
C7—N1	1.3819 (16)	C18—H18B	0.9700
C7—C8	1.4418 (16)	C19—C20	1.5169 (17)
C8—C11	1.4023 (17)	C19—H19A	0.9700
C8—C9	1.4373 (17)	C19—H19B	0.9700
C9—N2	1.3117 (16)	C20—C21	1.5218 (18)
C9—C10	1.4971 (16)	C20—H20A	0.9700
C10—H10A	0.9600	C20—H20B	0.9700
C10—H10B	0.9600	C21—H21A	0.9600
C10—H10C	0.9600	C21—H21B	0.9600
C11—N3	1.3230 (15)	C21—H21C	0.9600
C11—C12	1.4872 (16)	N1—N2	1.4030 (14)
C12—C17	1.3914 (16)	N3—H3A	0.921 (16)

C6—C1—C2	119.87 (11)	C15—C14—H14	119.9
C6—C1—N1	119.04 (11)	C13—C14—H14	119.9
C2—C1—N1	121.09 (11)	C16—C15—C14	120.05 (11)
C3—C2—C1	119.18 (13)	C16—C15—H15	120.0
C3—C2—H2	120.4	C14—C15—H15	120.0
C1—C2—H2	120.4	C15—C16—C17	120.31 (11)
C4—C3—C2	121.15 (12)	C15—C16—H16	119.8
C4—C3—H3	119.4	C17—C16—H16	119.8
C2—C3—H3	119.4	C16—C17—C12	119.91 (11)
C3—C4—C5	119.28 (12)	C16—C17—H17	120.0
C3—C4—H4	120.4	C12—C17—H17	120.0
C5—C4—H4	120.4	N3—C18—C19	109.09 (10)
C6—C5—C4	120.60 (13)	N3—C18—H18A	109.9
C6—C5—H5	119.7	C19—C18—H18A	109.9
C4—C5—H5	119.7	N3—C18—H18B	109.9
C5—C6—C1	119.90 (12)	C19—C18—H18B	109.9
C5—C6—H6	120.0	H18A—C18—H18B	108.3
C1—C6—H6	120.0	C20—C19—C18	112.19 (10)
O1—C7—N1	126.02 (11)	C20—C19—H19A	109.2
O1—C7—C8	129.22 (12)	C18—C19—H19A	109.2
N1—C7—C8	104.75 (10)	C20—C19—H19B	109.2
C11—C8—C9	133.54 (11)	C18—C19—H19B	109.2
C11—C8—C7	120.89 (11)	H19A—C19—H19B	107.9
C9—C8—C7	105.26 (10)	C19—C20—C21	112.34 (11)
N2—C9—C8	111.72 (11)	C19—C20—H20A	109.1
N2—C9—C10	117.95 (11)	C21—C20—H20A	109.1
C8—C9—C10	130.33 (11)	C19—C20—H20B	109.1
C9—C10—H10A	109.5	C21—C20—H20B	109.1
C9—C10—H10B	109.5	H20A—C20—H20B	107.9
H10A—C10—H10B	109.5	C20—C21—H21A	109.5
C9—C10—H10C	109.5	C20—C21—H21B	109.5
H10A—C10—H10C	109.5	H21A—C21—H21B	109.5
H10B—C10—H10C	109.5	C20—C21—H21C	109.5
N3—C11—C8	118.83 (11)	H21A—C21—H21C	109.5
N3—C11—C12	118.58 (11)	H21B—C21—H21C	109.5
C8—C11—C12	122.56 (11)	C7—N1—N2	111.99 (9)
C17—C12—C13	119.83 (11)	C7—N1—C1	129.28 (10)
C17—C12—C11	121.06 (10)	N2—N1—C1	118.52 (10)
C13—C12—C11	119.10 (10)	C9—N2—N1	106.27 (10)
C14—C13—C12	119.75 (11)	C11—N3—C18	127.75 (10)
C14—C13—H13	120.1	C11—N3—H3A	113.8 (10)
C12—C13—H13	120.1	C18—N3—H3A	118.3 (10)
C15—C14—C13	120.14 (11)

C6—C1—C2—C3	−0.55 (16)	C11—C12—C13—C14	−178.40 (11)
N1—C1—C2—C3	179.27 (10)	C12—C13—C14—C15	−0.77 (19)
C1—C2—C3—C4	1.43 (17)	C13—C14—C15—C16	0.0 (2)
C2—C3—C4—C5	−1.14 (18)	C14—C15—C16—C17	0.8 (2)
C3—C4—C5—C6	−0.03 (18)	C15—C16—C17—C12	−0.76 (19)
C4—C5—C6—C1	0.89 (17)	C13—C12—C17—C16	−0.06 (18)
C2—C1—C6—C5	−0.60 (17)	C11—C12—C17—C16	179.14 (11)
N1—C1—C6—C5	179.59 (10)	N3—C18—C19—C20	176.92 (9)
O1—C7—C8—C11	−4.43 (18)	C18—C19—C20—C21	177.25 (10)
N1—C7—C8—C11	174.38 (10)	O1—C7—N1—N2	178.95 (10)
O1—C7—C8—C9	−178.92 (11)	C8—C7—N1—N2	0.09 (12)
N1—C7—C8—C9	−0.11 (11)	O1—C7—N1—C1	4.41 (19)
C11—C8—C9—N2	−173.37 (12)	C8—C7—N1—C1	−174.45 (10)
C7—C8—C9—N2	0.10 (13)	C6—C1—N1—C7	174.10 (11)
C11—C8—C9—C10	6.6 (2)	C2—C1—N1—C7	−5.72 (17)
C7—C8—C9—C10	−179.93 (11)	C6—C1—N1—N2	−0.14 (15)
C9—C8—C11—N3	174.20 (12)	C2—C1—N1—N2	−179.96 (10)
C7—C8—C11—N3	1.54 (16)	C8—C9—N2—N1	−0.04 (12)
C9—C8—C11—C12	−3.62 (19)	C10—C9—N2—N1	179.98 (9)
C7—C8—C11—C12	−176.27 (10)	C7—N1—N2—C9	−0.03 (12)
N3—C11—C12—C17	116.65 (13)	C1—N1—N2—C9	175.16 (9)
C8—C11—C12—C17	−65.53 (16)	C8—C11—N3—C18	173.83 (11)
N3—C11—C12—C13	−64.14 (15)	C12—C11—N3—C18	−8.27 (17)
C8—C11—C12—C13	113.67 (13)	C19—C18—N3—C11	−173.20 (11)
C17—C12—C13—C14	0.82 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O1	0.921 (16)	1.873 (16)	2.6704 (14)	143.5 (14)
C13—H13···O1ⁱ	0.93	2.39	3.3175 (15)	172

Symmetry code: (i) −x+1, −y, −z+2.

Experimental details

Crystal data
Chemical formula	C₂₁H₂₃N₃O
M_r	333.42
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	9.5215 (9), 14.7867 (14), 12.8055 (12)
β (°)	100.645 (2)
V (Å³)	1771.9 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.28 × 0.20 × 0.16

Data collection
Diffractometer	Bruker SMART 1000 CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	16506, 4368, 3362
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.666

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.103, 1.01
No. of reflections	4368
No. of parameters	232
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.20

Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2003), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O1	0.921 (16)	1.873 (16)	2.6704 (14)	143.5 (14)
C13—H13···O1ⁱ	0.93	2.39	3.3175 (15)	172

Symmetry code: (i) −x+1, −y, −z+2.

Acknowledgements

This work was supported by the College of Chemistry and Molecular Engineering, East China University of Science and Technology.

References

Bernardino, A. M. R., Gomes, A. O., Charret, K. S., Freita, A. C. C., Machado, G. M. C., Canto-Cavalheiro, M. M., Leon, L. L. & Amaral, V. F. (2006). Eur. J. Med. Chem. 41, 80–87. Web of Science CrossRef PubMed CAS Google Scholar
Bruker (2001). SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2003). SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chi, X., Xiao, J., Yin, Y. & Xia, M. (2010). Acta Cryst. E66, o249. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, H.-W. (2010). Acta Cryst. E66, o1534. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zhang, H. Q., Li, J. Z., Zhang, Y. & Zhang, D. (2008). Chin. J. Inorg. Chem. 24, 990–993. Web of Science CSD CrossRef CAS Google Scholar
Zhang, H.-Q., Li, J.-Z., Zhang, Y., Zhang, D. & Su, Z.-H. (2007). Acta Cryst. E63, o3536. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zhen, X.-L. & Han, J.-R. (2005). Acta Cryst. E61, o4360–o4361. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 68| Part 4| April 2012| Page o969

doi:10.1107/S1600536812009166

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

4-[(Z)-(n-Butyl­amino)(phenyl)methyl­­idene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one

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Experimental

Crystal data

Data collection

Refinement

Supporting information

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References

organic compounds

4-[(Z)-(n-Butylamino)(phenyl)methylidene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one