Methyl 2-{1-[(Z)-3-methyl-5-oxo-1-phenyl-4,5-dihydro-1H-pyrazol-4-yl-idene]ethyl-amino}-3-phenyl-propanoate.

The mol-ecule of the title compound, C(22)H(23)N(3)O(3), exists in the enamine-keto form. A strong intra-molecular 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 = 377.43

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.096

S = 1.01

2366 reflections

256 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.08 e Å−3

Δρmin = −0.16 e Å−3

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.

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

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810017241/lx2128Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C22H23N3O3	F(000) = 400
Mr = 377.43	Dx = 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

Bruker SMART CCD area-detector diffractometer	2366 independent reflections
Radiation source: fine-focus sealed tube	1239 reflections with I > 2σ(I)
graphite	Rint = 0.028
Detector resolution: 10.0 pixels mm-1	θmax = 27.0°, θmin = 1.6°
φ and ω scans	h = −13→11
Absorption correction: multi-scan (SADABS; Sheldrick, 2000\bbr00)	k = −9→9
Tmin = 0.977, Tmax = 0.988	l = −13→16
6036 measured reflections

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(Fo2) + (0.0409P)2] where P = (Fo2 + 2Fc2)/3
2366 reflections	(Δ/σ)max = 0.001
256 parameters	Δρmax = 0.08 e Å−3
1 restraint	Δρmin = −0.16 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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