Methyl 2-{1-[(Z)-3-methyl-5-oxo-1-phenyl-4,5-dihydro-1H-pyrazol-4-yl­idene]ethyl­amino}-3-phenyl­propanoate

Zhu, H.; Shi, J.; Wei, Z.; Dai, R.; Zhang, X.

doi:10.1107/S1600536810017241

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 6| June 2010| Page o1352

https://doi.org/10.1107/S1600536810017241

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Methyl 2-{1-[(Z)-3-methyl-5-oxo-1-phenyl-4,5-dihydro-1H-pyrazol-4-ylidene]ethylamino}-3-phenylpropanoate

Hualing Zhu,^a ^* Jun Shi,^a Zhen Wei,^a Ronghua Dai ^a and Xin Zhang ^b

^aDepartment of Basic Science, Tianjin Agriculturial College, Tianjin Jinjing Road No. 22, Tianjin 300384, People's Republic of China, and ^bDepartment of Chemistry and Life Science, Tianjin Normal University, Tianjin 300387, People's Republic of China
^*Correspondence e-mail: zhuhualing2004@126.com

(Received 15 November 2009; accepted 11 May 2010; online 15 May 2010)

The molecule of the title compound, C₂₂H₂₃N₃O₃, exists in the enamine–keto form. A strong intramolecular N—H⋯O hydrogen bond occurs, generating an S(6) ring. The dihedral angle between the heterocycle and the adjacent phenyl ring is 3.75 (15)°.

Related literature

For the antibacterial activity of Schiff bases derived from 4-acyl-5-pyrazolones and metal complexes, see: Li et al. (1997 , 2004 ). For the biological activity of amino acid esters, see: Xiong et al. (1993 ). For related structures, see: Wang et al. (2003 ); Zhang et al. (2004 , 2010 ); Zhu et al. (2005 ).

Experimental

Crystal data

C₂₂H₂₃N₃O₃
M_r = 377.43
Monoclinic, P 2₁
a = 10.940 (1) Å
b = 7.2105 (7) Å
c = 12.867 (1) Å
β = 92.718 (2)°
V = 1013.84 (16) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 K
0.28 × 0.12 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2000\bbr00) T_min = 0.977, T_max = 0.988
6036 measured reflections
2366 independent reflections
1239 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.096
S = 1.01
2366 reflections
256 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.08 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯O1	0.86	1.98	2.695 (3)	141

Data collection: SMART (Bruker, 1999 ); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810017241/lx2128sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810017241/lx2128Isup2.hkl

checkCIF report

Comment top

The Schiff bases derived from 4-acyl-5-pyrazolones and their metal complexes have been studied widely for their high antibacterial activation [Li et al., 1997, 2004]. Since amino acid esters also possess good antibacterial and biological activations (Xiong et al., 1993), several Structures of Schiff bases derived from 4-acyl-5-pyrazolones and amino acid esters and closely related to the title compound have been reported [Zhu et al., 2005; Zhang et al., 2010]. We report the the crystal structure of the title compound.

In the molecule of the title compound, (Fig.1) atoms O1, C7, C8, C11 and atom N3 form a plane, the largest deviation being 0.024 (2) Å for atom C11. The dihedral angle between this mean plane and the pyrazolone ring of PMAP is 1.44 (3)°, indicating that they are essentially coplanar, as seen in Ethyl 2-{[(1Z)-(3- methyl-5-oxo-1-phenyl-4,5-dihydro-1H-pyrazol-4-ylidene) (p-tolyl)methyl]amino}-3-phenylpropanoate (1.52 (4)°; Zhang et al., 2010). The bond lengths within this part of the molecular lie between classical single-and double-bond lengths, indicating extensive conjugation. Atoms N3, C13, C14 and O2 are not coplanar, the torsion angle is -39.0 (4)°, similar to some other 4-acylpyrazolone schiff bases (Zhang et al. 2004; Wang et al. 2003). The bond lengths in this part of the molecular indicate that only C14—O2 is classical double bond, other bonds are classical single bonds. A strong intramolecular hydrogen bond N3—H3···O1 is observed (Table 1 & Fig. 1), stabilizing to an enamine–keto form.

Related literature top

For the antibacterial activity of Schiff bases derived from 4-acyl-5-pyrazolones and metal complexes, see: Li et al. (1997, 2004). For the biological activity of amino acid esters, see: Xiong et al. (1993). For related structures, see: Wang et al. (2003); Zhang et al. (2004, 2010); Zhu et al. (2005).

Experimental top

The title compound was synthesized by refluxing the mixture of HPMAP (15 m mol) and phenylalanine methyl ester (15m mol) in ethanol (100 ml) over a steam bath for about 4 h, then the solution was cooled down to room temperature. After four days, white block was obtained and dried in air. The product was recrystallized from ethanol which afforded colorless and acerate crystals suitable for X-ray analysis.

Structure description top

For the antibacterial activity of Schiff bases derived from 4-acyl-5-pyrazolones and metal complexes, see: Li et al. (1997, 2004). For the biological activity of amino acid esters, see: Xiong et al. (1993). For related structures, see: Wang et al. (2003); Zhang et al. (2004, 2010); Zhu et al. (2005).

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (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 radius.

Methyl 2-{1-[(Z)-3-methyl-5-oxo-1-phenyl-4,5-dihydro-1H-pyrazol- 4-ylidene]ethylamino}-3-phenylpropanoate top

Crystal data top

C₂₂H₂₃N₃O₃	F(000) = 400
M_r = 377.43	D_x = 1.236 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
a = 10.940 (1) Å	Cell parameters from 1220 reflections
b = 7.2105 (7) Å	θ = 3.2–22.4°
c = 12.867 (1) Å	µ = 0.08 mm⁻¹
β = 92.718 (2)°	T = 296 K
V = 1013.84 (16) Å³	Block, colorless
Z = 2	0.28 × 0.12 × 0.10 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2366 independent reflections
Radiation source: fine-focus sealed tube	1239 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
Detector resolution: 10.0 pixels mm^-1	θ_max = 27.0°, θ_min = 1.6°
φ and ω scans	h = −13→11
Absorption correction: multi-scan (SADABS; Sheldrick, 2000\bbr00)	k = −9→9
T_min = 0.977, T_max = 0.988	l = −13→16
6036 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)] = 0.037	Hydrogen site location: difference Fourier map
wR(F²) = 0.096	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0409P)²] where P = (F_o² + 2F_c²)/3
2366 reflections	(Δ/σ)_max = 0.001
256 parameters	Δρ_max = 0.08 e Å⁻³
1 restraint	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₂₂H₂₃N₃O₃	V = 1013.84 (16) Å³
M_r = 377.43	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 10.940 (1) Å	µ = 0.08 mm⁻¹
b = 7.2105 (7) Å	T = 296 K
c = 12.867 (1) Å	0.28 × 0.12 × 0.10 mm
β = 92.718 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2366 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2000\bbr00)	1239 reflections with I > 2σ(I)
T_min = 0.977, T_max = 0.988	R_int = 0.028
6036 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	1 restraint
wR(F²) = 0.096	H-atom parameters constrained
S = 1.01	Δρ_max = 0.08 e Å⁻³
2366 reflections	Δρ_min = −0.16 e Å⁻³
256 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 > 2sigma(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	0.69537 (16)	0.7004 (4)	0.63222 (13)	0.0812 (6)
O2	0.9385 (2)	0.5317 (4)	0.4573 (2)	0.0951 (8)
O3	0.9296 (2)	0.4530 (3)	0.28897 (18)	0.0818 (7)
N1	0.49129 (18)	0.7209 (4)	0.67625 (16)	0.0594 (6)
N2	0.37536 (19)	0.7237 (4)	0.62394 (18)	0.0662 (6)
N3	0.7085 (2)	0.6887 (4)	0.42371 (17)	0.0681 (7)
H3	0.7408	0.6814	0.4858	0.082*
C1	0.3903 (3)	0.7353 (6)	0.8383 (2)	0.0798 (10)
H1	0.3156	0.7472	0.8012	0.096*
C2	0.3948 (4)	0.7310 (7)	0.9457 (3)	0.1043 (12)
H2	0.3226	0.7392	0.9809	0.125*
C3	0.5037 (5)	0.7148 (8)	1.0007 (3)	0.1151 (14)
H3A	0.5060	0.7114	1.0730	0.138*
C4	0.6103 (3)	0.7035 (8)	0.9487 (2)	0.1075 (13)
H4	0.6849	0.6941	0.9860	0.129*
C5	0.6072 (3)	0.7060 (6)	0.8416 (2)	0.0853 (10)
H5	0.6794	0.6971	0.8066	0.102*
C6	0.4968 (3)	0.7219 (5)	0.7866 (2)	0.0626 (7)
C7	0.5836 (2)	0.7091 (5)	0.6073 (2)	0.0608 (7)
C8	0.5237 (2)	0.7100 (5)	0.5063 (2)	0.0534 (6)
C9	0.3959 (2)	0.7185 (5)	0.5250 (2)	0.0595 (7)
C10	0.2866 (2)	0.7155 (6)	0.4494 (2)	0.0834 (10)
H10A	0.2130	0.7153	0.4871	0.125*
H10B	0.2892	0.6059	0.4072	0.125*
H10C	0.2880	0.8233	0.4056	0.125*
C11	0.5879 (2)	0.7059 (5)	0.4158 (2)	0.0563 (7)
C12	0.5269 (2)	0.7185 (6)	0.3096 (2)	0.0727 (8)
H12A	0.5209	0.5969	0.2794	0.109*
H12B	0.5741	0.7971	0.2666	0.109*
H12C	0.4463	0.7697	0.3146	0.109*
C13	0.7929 (2)	0.6804 (5)	0.3398 (2)	0.0646 (8)
H13	0.7495	0.6375	0.2759	0.077*
C14	0.8937 (3)	0.5450 (5)	0.3710 (3)	0.0677 (9)
C15	1.0389 (3)	0.3383 (6)	0.3056 (3)	0.1081 (14)
H15A	1.0281	0.2559	0.3631	0.162*
H15B	1.1086	0.4164	0.3206	0.162*
H15C	1.0518	0.2670	0.2441	0.162*
C16	0.8488 (3)	0.8723 (5)	0.3216 (3)	0.0724 (9)
H16A	0.7833	0.9626	0.3131	0.087*
H16B	0.8991	0.9071	0.3826	0.087*
C17	0.9252 (3)	0.8793 (4)	0.2280 (3)	0.0645 (8)
C18	1.0502 (3)	0.8632 (5)	0.2357 (3)	0.0886 (11)
H18	1.0890	0.8466	0.3009	0.106*
C19	1.1202 (4)	0.8709 (6)	0.1491 (5)	0.1149 (16)
H19	1.2049	0.8596	0.1561	0.138*
C20	1.0639 (5)	0.8953 (7)	0.0535 (4)	0.1186 (16)
H20	1.1104	0.9008	−0.0051	0.142*
C21	0.9411 (5)	0.9114 (7)	0.0431 (3)	0.1104 (14)
H21	0.9030	0.9288	−0.0223	0.133*
C22	0.8718 (3)	0.9019 (5)	0.1308 (3)	0.0847 (11)
H22	0.7871	0.9111	0.1231	0.102*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0527 (12)	0.1241 (19)	0.0665 (13)	−0.0042 (16)	−0.0012 (9)	0.0002 (17)
O2	0.0909 (17)	0.113 (2)	0.0801 (18)	0.0257 (16)	−0.0114 (13)	0.0023 (16)
O3	0.0824 (16)	0.0755 (15)	0.0886 (19)	0.0130 (13)	0.0146 (13)	−0.0103 (14)
N1	0.0538 (13)	0.0666 (16)	0.0580 (15)	−0.0033 (16)	0.0047 (11)	0.0003 (17)
N2	0.0544 (14)	0.0725 (17)	0.0719 (16)	0.0014 (15)	0.0045 (12)	0.0012 (19)
N3	0.0611 (15)	0.088 (2)	0.0548 (14)	0.0066 (16)	0.0041 (11)	0.0009 (17)
C1	0.077 (2)	0.092 (3)	0.071 (2)	0.000 (2)	0.0145 (16)	−0.010 (2)
C2	0.113 (3)	0.128 (4)	0.075 (3)	0.004 (3)	0.029 (2)	−0.012 (3)
C3	0.138 (3)	0.148 (4)	0.060 (2)	0.007 (4)	0.009 (2)	−0.007 (3)
C4	0.105 (3)	0.150 (4)	0.066 (2)	−0.003 (4)	−0.004 (2)	0.002 (4)
C5	0.076 (2)	0.115 (3)	0.064 (2)	−0.001 (3)	0.0007 (16)	0.001 (3)
C6	0.0731 (19)	0.0571 (18)	0.0586 (19)	−0.0032 (19)	0.0125 (15)	−0.001 (2)
C7	0.0567 (18)	0.0596 (19)	0.0664 (18)	−0.001 (2)	0.0063 (15)	0.001 (2)
C8	0.0504 (15)	0.0552 (17)	0.0546 (16)	−0.0013 (17)	0.0036 (13)	0.001 (2)
C9	0.0558 (17)	0.0545 (17)	0.0681 (19)	−0.0005 (18)	0.0007 (13)	0.002 (2)
C10	0.0553 (17)	0.110 (3)	0.084 (2)	0.002 (2)	−0.0061 (14)	−0.004 (3)
C11	0.0563 (18)	0.0512 (17)	0.0609 (18)	−0.0009 (18)	−0.0023 (13)	0.000 (2)
C12	0.0757 (19)	0.080 (2)	0.0625 (18)	0.009 (2)	0.0011 (14)	0.002 (2)
C13	0.0619 (18)	0.076 (2)	0.0568 (18)	0.0028 (18)	0.0082 (14)	0.0025 (18)
C14	0.057 (2)	0.066 (2)	0.080 (3)	−0.0016 (17)	0.0078 (19)	0.000 (2)
C15	0.091 (3)	0.089 (3)	0.146 (4)	0.037 (2)	0.018 (2)	−0.006 (3)
C16	0.076 (2)	0.069 (2)	0.073 (2)	0.0084 (18)	0.0089 (18)	0.0011 (19)
C17	0.060 (2)	0.064 (2)	0.069 (2)	0.0048 (17)	0.0073 (17)	0.0016 (18)
C18	0.073 (3)	0.092 (3)	0.102 (3)	0.003 (2)	0.008 (2)	0.000 (2)
C19	0.072 (3)	0.116 (4)	0.158 (5)	−0.002 (3)	0.026 (3)	0.001 (4)
C20	0.115 (4)	0.107 (4)	0.139 (5)	0.001 (3)	0.060 (3)	0.007 (3)
C21	0.121 (4)	0.127 (4)	0.086 (3)	0.011 (3)	0.027 (3)	0.014 (3)
C22	0.074 (2)	0.101 (3)	0.079 (3)	0.010 (2)	0.010 (2)	0.004 (2)

Geometric parameters (Å, º) top

O1—C7	1.251 (3)	C10—H10B	0.9600
O2—C14	1.197 (4)	C10—H10C	0.9600
O3—C14	1.322 (4)	C11—C12	1.495 (3)
O3—C15	1.462 (4)	C12—H12A	0.9600
N1—C7	1.378 (3)	C12—H12B	0.9600
N1—N2	1.407 (3)	C12—H12C	0.9600
N1—C6	1.418 (3)	C13—C14	1.512 (4)
N2—C9	1.304 (3)	C13—C16	1.535 (4)
N3—C11	1.325 (3)	C13—H13	0.9800
N3—C13	1.454 (3)	C15—H15A	0.9600
N3—H3	0.8600	C15—H15B	0.9600
C1—C6	1.372 (4)	C15—H15C	0.9600
C1—C2	1.382 (4)	C16—C17	1.499 (4)
C1—H1	0.9300	C16—H16A	0.9700
C2—C3	1.362 (5)	C16—H16B	0.9700
C2—H2	0.9300	C17—C22	1.365 (4)
C3—C4	1.374 (5)	C17—C18	1.371 (4)
C3—H3A	0.9300	C18—C19	1.382 (5)
C4—C5	1.376 (4)	C18—H18	0.9300
C4—H4	0.9300	C19—C20	1.361 (5)
C5—C6	1.376 (4)	C19—H19	0.9300
C5—H5	0.9300	C20—C21	1.349 (5)
C7—C8	1.427 (3)	C20—H20	0.9300
C8—C11	1.388 (3)	C21—C22	1.390 (5)
C8—C9	1.431 (3)	C21—H21	0.9300
C9—C10	1.506 (3)	C22—H22	0.9300
C10—H10A	0.9600

C14—O3—C15	116.0 (3)	C11—C12—H12B	109.5
C7—N1—N2	111.3 (2)	H12A—C12—H12B	109.5
C7—N1—C6	130.4 (2)	C11—C12—H12C	109.5
N2—N1—C6	118.2 (2)	H12A—C12—H12C	109.5
C9—N2—N1	105.9 (2)	H12B—C12—H12C	109.5
C11—N3—C13	127.7 (2)	N3—C13—C14	108.1 (3)
C11—N3—H3	116.1	N3—C13—C16	110.4 (3)
C13—N3—H3	116.1	C14—C13—C16	109.4 (2)
C6—C1—C2	119.5 (3)	N3—C13—H13	109.7
C6—C1—H1	120.2	C14—C13—H13	109.7
C2—C1—H1	120.2	C16—C13—H13	109.7
C3—C2—C1	120.7 (3)	O2—C14—O3	125.2 (3)
C3—C2—H2	119.7	O2—C14—C13	124.0 (3)
C1—C2—H2	119.7	O3—C14—C13	110.7 (3)
C2—C3—C4	119.6 (3)	O3—C15—H15A	109.5
C2—C3—H3A	120.2	O3—C15—H15B	109.5
C4—C3—H3A	120.2	H15A—C15—H15B	109.5
C3—C4—C5	120.4 (3)	O3—C15—H15C	109.5
C3—C4—H4	119.8	H15A—C15—H15C	109.5
C5—C4—H4	119.8	H15B—C15—H15C	109.5
C6—C5—C4	119.7 (3)	C17—C16—C13	113.2 (3)
C6—C5—H5	120.2	C17—C16—H16A	108.9
C4—C5—H5	120.2	C13—C16—H16A	108.9
C1—C6—C5	120.1 (3)	C17—C16—H16B	108.9
C1—C6—N1	119.3 (3)	C13—C16—H16B	108.9
C5—C6—N1	120.6 (3)	H16A—C16—H16B	107.7
O1—C7—N1	125.1 (2)	C22—C17—C18	117.3 (3)
O1—C7—C8	129.4 (2)	C22—C17—C16	120.6 (3)
N1—C7—C8	105.5 (2)	C18—C17—C16	122.1 (3)
C11—C8—C7	122.3 (2)	C17—C18—C19	121.8 (4)
C11—C8—C9	132.8 (2)	C17—C18—H18	119.1
C7—C8—C9	104.9 (2)	C19—C18—H18	119.1
N2—C9—C8	112.4 (2)	C20—C19—C18	119.3 (4)
N2—C9—C10	117.6 (2)	C20—C19—H19	120.3
C8—C9—C10	130.0 (2)	C18—C19—H19	120.3
C9—C10—H10A	109.5	C21—C20—C19	120.5 (4)
C9—C10—H10B	109.5	C21—C20—H20	119.8
H10A—C10—H10B	109.5	C19—C20—H20	119.8
C9—C10—H10C	109.5	C20—C21—C22	119.6 (4)
H10A—C10—H10C	109.5	C20—C21—H21	120.2
H10B—C10—H10C	109.5	C22—C21—H21	120.2
N3—C11—C8	118.6 (2)	C17—C22—C21	121.6 (3)
N3—C11—C12	118.4 (2)	C17—C22—H22	119.2
C8—C11—C12	122.9 (2)	C21—C22—H22	119.2
C11—C12—H12A	109.5

C7—N1—N2—C9	−1.6 (4)	C7—C8—C9—C10	−177.3 (4)
C6—N1—N2—C9	−178.8 (3)	C13—N3—C11—C8	179.6 (3)
C6—C1—C2—C3	0.4 (7)	C13—N3—C11—C12	0.2 (5)
C1—C2—C3—C4	0.3 (9)	C7—C8—C11—N3	4.4 (5)
C2—C3—C4—C5	−0.8 (9)	C9—C8—C11—N3	−176.7 (3)
C3—C4—C5—C6	0.6 (8)	C7—C8—C11—C12	−176.1 (3)
C2—C1—C6—C5	−0.6 (6)	C9—C8—C11—C12	2.7 (6)
C2—C1—C6—N1	178.2 (4)	C11—N3—C13—C14	−143.2 (3)
C4—C5—C6—C1	0.1 (7)	C11—N3—C13—C16	97.2 (4)
C4—C5—C6—N1	−178.7 (4)	C15—O3—C14—O2	−5.2 (5)
C7—N1—C6—C1	179.9 (4)	C15—O3—C14—C13	171.1 (3)
N2—N1—C6—C1	−3.4 (5)	N3—C13—C14—O2	−39.0 (4)
C7—N1—C6—C5	−1.2 (6)	C16—C13—C14—O2	81.2 (4)
N2—N1—C6—C5	175.4 (3)	N3—C13—C14—O3	144.8 (3)
N2—N1—C7—O1	−178.4 (3)	C16—C13—C14—O3	−95.1 (3)
C6—N1—C7—O1	−1.7 (6)	N3—C13—C16—C17	−173.2 (3)
N2—N1—C7—C8	1.8 (4)	C14—C13—C16—C17	68.1 (4)
C6—N1—C7—C8	178.6 (3)	C13—C16—C17—C22	82.0 (4)
O1—C7—C8—C11	−1.9 (6)	C13—C16—C17—C18	−97.8 (4)
N1—C7—C8—C11	177.8 (3)	C22—C17—C18—C19	0.6 (5)
O1—C7—C8—C9	179.0 (4)	C16—C17—C18—C19	−179.6 (4)
N1—C7—C8—C9	−1.3 (4)	C17—C18—C19—C20	0.0 (7)
N1—N2—C9—C8	0.7 (4)	C18—C19—C20—C21	−0.1 (7)
N1—N2—C9—C10	178.6 (3)	C19—C20—C21—C22	−0.4 (7)
C11—C8—C9—N2	−178.6 (4)	C18—C17—C22—C21	−1.1 (6)
C7—C8—C9—N2	0.4 (4)	C16—C17—C22—C21	179.1 (4)
C11—C8—C9—C10	3.8 (7)	C20—C21—C22—C17	1.0 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O1	0.86	1.98	2.695 (3)	141

Experimental details

Crystal data
Chemical formula	C₂₂H₂₃N₃O₃
M_r	377.43
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	296
a, b, c (Å)	10.940 (1), 7.2105 (7), 12.867 (1)
β (°)	92.718 (2)
V (Å³)	1013.84 (16)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.28 × 0.12 × 0.10

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 2000\bbr00)
T_min, T_max	0.977, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	6036, 2366, 1239
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.638

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.096, 1.01
No. of reflections	2366
No. of parameters	256
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.08, −0.16

Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O1	0.86	1.98	2.695 (3)	140.5

Acknowledgements

The authors thank the Science Development Committee of Tianjin Agricultural College for partial funding (research grant No. 2007029).

References

Bruker (1999). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Li, J. Z., Jiang, L. & An, Y. M. (2004). Chin. J. Appl. Chem. 21, 150–153. CAS Google Scholar
Li, J. Z., Yu, W. J. & Du, X. Y. (1997). Chin. J. Appl. Chem. 14, 98–100. CAS Google Scholar
Sheldrick, G. M. (2000). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, J.-L., Yang, Y., Zhang, X. & Miao, F.-M. (2003). Acta Cryst. E59, o430–o432. Web of Science CSD CrossRef IUCr Journals Google Scholar
Xiong, G. H., Yang, Z. M. & Guo, A. L. (1993). Fine Chem. 6, 1–3. Google Scholar
Zhang, X., Huang, M., Du, C. & Han, J. (2010). Acta Cryst. E66, o273. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zhang, X., Zhu, H., Xu, H. & Dong, M. (2004). Acta Cryst. E60, o1157–o1158. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zhu, H., Zhang, X., Song, Y., Xu, H. & Dong, M. (2005). Acta Cryst. E61, o2387–o2388. Web of Science CSD CrossRef IUCr Journals Google Scholar

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

Methyl 2-{1-[(Z)-3-methyl-5-oxo-1-phenyl-4,5-di­hydro-1H-pyrazol-4-yl­­idene]ethyl­amino}-3-phenyl­propanoate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Methyl 2-{1-[(Z)-3-methyl-5-oxo-1-phenyl-4,5-dihydro-1H-pyrazol-4-ylidene]ethylamino}-3-phenylpropanoate