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

Zhang, X.; Sun, C.; Li, F.; Zhang, H.

doi:10.1107/S1600536812010343

organic compounds

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ISSN: 2056-9890

Volume 68| Part 4| April 2012| Page o1062

doi:10.1107/S1600536812010343

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

Xin Zhang,^a ^* Chen Sun,^a Fei-ran Li ^a and Hua Zhang ^a

^aCollege of Chemistry, Tianjin Normal University, Tianjin 300387, People's Republic of China
^*Correspondence e-mail: zxin_tj@126.com

(Received 13 January 2012; accepted 8 March 2012; online 14 March 2012)

The molecule of the title compound, C₂₇H₂₄N₄O₅, exists in the keto–enamine tautomeric form, stabilized by an intramolecular N—H⋯O hydrogen bond. An intramolecular C—H⋯·O hydrogen bond also occurs. In the crystal, C—H⋯O hydrogen bonds link the molecules into chains.

Related literature

For general background to Schiff bases in coordination chemistry, see: Wu et al. (1993 ); Harrop et al. (2003 ); Habibi et al. (2007 ). For antibacterial properties of Schiff bases derived from 4-acyl-5-pyrazolone and their metal complexes, see: Li et al. (1997 , 2004 ). For the antibacterial and biological activity of amino acid esters, see: Xiong et al. (1993 ). For related structures, see: Wang et al. (2003 ); Zhang et al. (2005 ). For synthetic details, see: Remya et al. (2005 ). For standard bond lengths, see: Allen et al. (1987 ).

Experimental

Crystal data

C₂₇H₂₄N₄O₅
M_r = 484.50
Monoclinic, P 2₁
a = 6.7713 (16) Å
b = 8.917 (2) Å
c = 20.339 (5) Å
β = 92.489 (4)°
V = 1226.9 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.20 × 0.16 × 0.12 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.980, T_max = 0.989
6305 measured reflections
2315 independent reflections
1855 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.106
S = 1.07
2315 reflections
327 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4⋯O1	0.86	2.04	2.738 (4)	138
C1—H1⋯O1	0.93	2.41	3.001 (4)	121
C20—H20A⋯O1ⁱ	0.96	2.55	3.385 (5)	145
Symmetry code: (i) x-1, y, z.

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; 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: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812010343/yk2041sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812010343/yk2041Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812010343/yk2041Isup3.cml

checkCIF report

Comment top

In recent years, Schiff bases play an important role in the development of coordination chemistry related to catalysis and enzymatic reactions, magnetism, and molecular architectures (Wu et al., 1993; Harrop et al., 2003; Habibi et al., 2007). In recent years, the Schiff bases derived from 4–acyl–5–pyrazolone and their metal complexes have been studied widely for their high antibacterial activity (Li et al., 1997, 2004). Both 1–phenyl–3–methyl–4–(p–nitro–benzyl)–5–pyrazolone and its metal complexes are widely used and well known for their analgetic activity (Remya et al., 2005). Amino acid esters also demonstrate high antibacterial and biological activity (Xiong et al., 1993). Structure of Schiff base derived from 4–acyl–5–pyrazolone and amino acid ester, closely related to the title compound, has been reported (Zhang et al., 2005).

The molecular structure of the title compound is presented in Fig. 1, and the numerical results are given in tables below. Atoms O1, C9, C8, C11 and N4 form a plane, the largest deviation being 0.021 (4) Å for atom C11. The dihedral angle between this mean plane and the pyrazolone ring is 1.2 (1)°, indicating that they are essentially coplanar, as seen in 4–{[3,4–dihydro–5–methyl–3–oxo–2–phenyl–2H–pyrazol–4–ylidene]–(phenyl)methyl]amino}–1,5–dimethyl–2–phenyl–1H–pyrazol–3(2H)–one [3.56 (3)°; Wang et al., 2003]. The bond lengths within central part of the molecule lie between typical single- and double- bond lengths, indicating extensive conjugation. A strong intramolecular N—H···O hydrogen bond is observed, stabilizing the enamine-keto tautomeric form. In the crystal structure, intermolecular C1—H1···O4 hydrogen bonds link the molecules into chains, shown in Fig. 2.

Related literature top

For general background to Schiff bases in coordination chemistry, see: Wu et al. (1993); Harrop et al. (2003); Habibi et al. (2007). For antibacterial properties of Schiff bases derived from 4-acyl-5-pyrazolone and their metal complexes, see: Li et al. (1997, 2004). For the antibacterial and biological activity of amino acid esters, see: Xiong et al. (1993). For related structures, see: Wang et al. (2003); Zhang et al. (2005). For synthetic details, see: Remya et al. (2005). For standard bond lengths, see: Allen et al. (1987).

Experimental top

The title compound was synthesized by refluxing a mixture of 1–phenyl–3—methyl–4–(p–nitro–benzyl)–5–pyrazolone (15 mmol) (Remya et al., 2005) and phenylalanine methyl ester (15 mmol) in ethanol (100 ml) for about 5 h. The product was recrystallized from ethanol, affording pale yellow crystals suitable for X–ray analysis.

Structure description top

For general background to Schiff bases in coordination chemistry, see: Wu et al. (1993); Harrop et al. (2003); Habibi et al. (2007). For antibacterial properties of Schiff bases derived from 4-acyl-5-pyrazolone and their metal complexes, see: Li et al. (1997, 2004). For the antibacterial and biological activity of amino acid esters, see: Xiong et al. (1993). For related structures, see: Wang et al. (2003); Zhang et al. (2005). For synthetic details, see: Remya et al. (2005). For standard bond lengths, see: Allen et al. (1987).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title molecule with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. The chain formed by the intermolecular C—H···O hydrogen bonds (shown by dashed lines).

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

Crystal data top

C₂₇H₂₄N₄O₅	F(000) = 508
M_r = 484.50	D_x = 1.312 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 2125 reflections
a = 6.7713 (16) Å	θ = 2.5–22.4°
b = 8.917 (2) Å	µ = 0.09 mm⁻¹
c = 20.339 (5) Å	T = 296 K
β = 92.489 (4)°	Block, colourless
V = 1226.9 (5) Å³	0.20 × 0.16 × 0.12 mm
Z = 2

Data collection top

Bruker APEXII CCD diffractometer	2315 independent reflections
Radiation source: fine-focus sealed tube	1855 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
φ and ω scan	θ_max = 25.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −8→7
T_min = 0.980, T_max = 0.989	k = −10→10
6305 measured reflections	l = −24→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) = 0.106	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0582P)² + 0.0914P] where P = (F_o² + 2F_c²)/3
2315 reflections	(Δ/σ)_max < 0.001
327 parameters	Δρ_max = 0.26 e Å⁻³
1 restraint	Δρ_min = −0.15 e Å⁻³

Crystal data top

C₂₇H₂₄N₄O₅	V = 1226.9 (5) Å³
M_r = 484.50	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 6.7713 (16) Å	µ = 0.09 mm⁻¹
b = 8.917 (2) Å	T = 296 K
c = 20.339 (5) Å	0.20 × 0.16 × 0.12 mm
β = 92.489 (4)°

Data collection top

Bruker APEXII CCD diffractometer	2315 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	1855 reflections with I > 2σ(I)
T_min = 0.980, T_max = 0.989	R_int = 0.021
6305 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	1 restraint
wR(F²) = 0.106	H-atom parameters constrained
S = 1.07	Δρ_max = 0.26 e Å⁻³
2315 reflections	Δρ_min = −0.15 e Å⁻³
327 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	0.2384 (4)	−0.1136 (2)	0.34497 (13)	0.0631 (7)
O2	−0.7694 (4)	0.4350 (4)	0.12919 (15)	0.0803 (9)
O3	−0.5325 (5)	0.4977 (5)	0.06804 (18)	0.1058 (12)
O4	−0.3079 (4)	−0.3075 (3)	0.31388 (15)	0.0683 (7)
O5	−0.4842 (5)	−0.3580 (4)	0.22187 (18)	0.1000 (11)
N1	0.3237 (4)	0.1290 (3)	0.38007 (13)	0.0506 (7)
N2	0.2558 (4)	0.2758 (3)	0.36907 (15)	0.0579 (7)
N3	−0.5986 (4)	0.4262 (4)	0.11306 (16)	0.0645 (8)
N4	−0.0863 (4)	−0.0999 (3)	0.26012 (15)	0.0551 (7)
H4	−0.0086	−0.1510	0.2861	0.066*
C1	0.6183 (5)	−0.0145 (5)	0.4130 (2)	0.0709 (11)
H1	0.5785	−0.0909	0.3842	0.085*
C2	0.7941 (6)	−0.0259 (6)	0.4492 (2)	0.0879 (14)
H2	0.8727	−0.1104	0.4444	0.105*
C3	0.8550 (7)	0.0833 (8)	0.4916 (3)	0.1011 (17)
H3	0.9744	0.0747	0.5156	0.121*
C4	0.7377 (8)	0.2064 (9)	0.4983 (3)	0.118 (2)
H4A	0.7776	0.2803	0.5283	0.142*
C5	0.5612 (7)	0.2250 (6)	0.4621 (2)	0.0901 (15)
H5	0.4852	0.3112	0.4661	0.108*
C6	0.5025 (5)	0.1097 (4)	0.41960 (16)	0.0534 (8)
C7	0.1051 (5)	0.2653 (4)	0.32700 (17)	0.0508 (8)
C8	0.0671 (4)	0.1120 (3)	0.30814 (15)	0.0437 (7)
C9	0.2132 (4)	0.0246 (4)	0.34512 (16)	0.0474 (8)
C10	0.0044 (6)	0.4069 (4)	0.3050 (3)	0.0824 (13)
H10A	0.0556	0.4893	0.3310	0.124*
H10B	−0.1352	0.3979	0.3106	0.124*
H10C	0.0281	0.4245	0.2595	0.124*
C11	−0.0733 (4)	0.0480 (4)	0.26523 (15)	0.0449 (8)
C12	−0.2120 (4)	0.1434 (3)	0.22373 (15)	0.0423 (7)
C13	−0.1507 (5)	0.2096 (4)	0.16670 (17)	0.0514 (8)
H13	−0.0236	0.1915	0.1530	0.062*
C14	−0.2753 (5)	0.3019 (4)	0.12978 (17)	0.0545 (9)
H14	−0.2339	0.3465	0.0914	0.065*
C15	−0.4630 (4)	0.3264 (4)	0.15121 (17)	0.0489 (8)
C16	−0.5284 (5)	0.2614 (4)	0.20677 (18)	0.0593 (9)
H16	−0.6562	0.2791	0.2199	0.071*
C17	−0.4023 (5)	0.1686 (4)	0.24343 (17)	0.0564 (9)
H17	−0.4454	0.1231	0.2814	0.068*
C18	−0.2165 (5)	−0.1856 (4)	0.21573 (19)	0.0591 (9)
H18	−0.3020	−0.1133	0.1920	0.071*
C19	−0.3515 (6)	−0.2928 (4)	0.2507 (2)	0.0636 (10)
C20	−0.4402 (7)	−0.4046 (5)	0.3506 (3)	0.0948 (15)
H20A	−0.5692	−0.3599	0.3509	0.142*
H20B	−0.3884	−0.4159	0.3950	0.142*
H20C	−0.4494	−0.5012	0.3299	0.142*
C21	−0.0987 (6)	−0.2697 (4)	0.1635 (2)	0.0731 (11)
H21A	−0.0013	−0.3339	0.1857	0.088*
H21B	−0.1884	−0.3331	0.1375	0.088*
C22	0.0040 (6)	−0.1652 (4)	0.1186 (2)	0.0635 (10)
C23	−0.0986 (7)	−0.0965 (5)	0.0657 (2)	0.0777 (12)
H23	−0.2311	−0.1194	0.0570	0.093*
C24	−0.0046 (8)	0.0060 (6)	0.0261 (2)	0.0874 (14)
H24	−0.0743	0.0508	−0.0091	0.105*
C25	0.1903 (8)	0.0413 (6)	0.0387 (3)	0.0911 (14)
H25	0.2528	0.1109	0.0126	0.109*
C26	0.2911 (7)	−0.0259 (6)	0.0894 (3)	0.0903 (14)
H26	0.4238	−0.0028	0.0976	0.108*
C27	0.2016 (6)	−0.1274 (5)	0.1291 (2)	0.0816 (13)
H27	0.2746	−0.1717	0.1637	0.098*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0668 (15)	0.0396 (15)	0.0809 (17)	0.0042 (11)	−0.0176 (12)	0.0071 (12)
O2	0.0508 (15)	0.087 (2)	0.103 (2)	0.0157 (14)	−0.0078 (14)	0.0168 (17)
O3	0.086 (2)	0.128 (3)	0.104 (2)	0.033 (2)	0.0136 (17)	0.062 (2)
O4	0.0676 (15)	0.0495 (15)	0.088 (2)	−0.0010 (13)	0.0039 (14)	0.0021 (14)
O5	0.093 (2)	0.072 (2)	0.132 (3)	−0.0315 (19)	−0.0316 (19)	0.004 (2)
N1	0.0474 (14)	0.0488 (16)	0.0552 (16)	−0.0002 (13)	−0.0033 (12)	−0.0010 (14)
N2	0.0578 (16)	0.0465 (16)	0.0688 (19)	0.0048 (14)	−0.0034 (14)	−0.0125 (14)
N3	0.0571 (18)	0.064 (2)	0.072 (2)	0.0105 (15)	−0.0038 (15)	0.0147 (17)
N4	0.0621 (17)	0.0311 (15)	0.0703 (19)	0.0030 (13)	−0.0170 (14)	0.0037 (13)
C1	0.066 (2)	0.071 (3)	0.074 (3)	0.007 (2)	−0.0150 (19)	−0.001 (2)
C2	0.064 (2)	0.095 (4)	0.102 (3)	0.009 (3)	−0.020 (2)	0.012 (3)
C3	0.062 (3)	0.145 (5)	0.094 (4)	−0.008 (3)	−0.028 (2)	0.003 (4)
C4	0.089 (4)	0.153 (6)	0.109 (4)	−0.005 (4)	−0.039 (3)	−0.045 (4)
C5	0.073 (3)	0.104 (4)	0.092 (3)	0.004 (2)	−0.018 (2)	−0.034 (3)
C6	0.0458 (17)	0.070 (2)	0.0444 (19)	−0.0047 (18)	0.0009 (13)	0.0002 (17)
C7	0.0468 (18)	0.0410 (17)	0.065 (2)	0.0064 (15)	0.0035 (15)	−0.0057 (16)
C8	0.0424 (16)	0.0355 (17)	0.0530 (19)	0.0032 (14)	−0.0005 (13)	0.0001 (14)
C9	0.0440 (18)	0.046 (2)	0.052 (2)	0.0001 (14)	0.0027 (14)	−0.0001 (15)
C10	0.080 (3)	0.046 (2)	0.119 (4)	0.016 (2)	−0.025 (2)	−0.018 (2)
C11	0.0440 (17)	0.0440 (19)	0.0469 (19)	0.0036 (14)	0.0046 (14)	0.0020 (14)
C12	0.0439 (16)	0.0315 (15)	0.0514 (18)	0.0007 (13)	0.0008 (13)	−0.0007 (14)
C13	0.0421 (17)	0.0472 (18)	0.065 (2)	0.0044 (15)	0.0073 (15)	0.0034 (17)
C14	0.0540 (19)	0.053 (2)	0.057 (2)	0.0031 (16)	0.0082 (15)	0.0122 (16)
C15	0.0441 (16)	0.0418 (18)	0.060 (2)	0.0067 (14)	−0.0031 (15)	0.0012 (15)
C16	0.0439 (17)	0.069 (2)	0.065 (2)	0.0101 (18)	0.0069 (15)	0.011 (2)
C17	0.0525 (18)	0.060 (2)	0.057 (2)	0.0054 (17)	0.0089 (15)	0.0169 (16)
C18	0.067 (2)	0.0341 (17)	0.075 (3)	0.0029 (16)	−0.0178 (19)	−0.0030 (17)
C19	0.064 (2)	0.0346 (17)	0.092 (3)	0.0031 (17)	−0.007 (2)	−0.0013 (19)
C20	0.088 (3)	0.063 (3)	0.136 (4)	−0.007 (2)	0.036 (3)	0.011 (3)
C21	0.086 (3)	0.045 (2)	0.087 (3)	0.0055 (19)	−0.007 (2)	−0.009 (2)
C22	0.072 (2)	0.047 (2)	0.070 (2)	0.0085 (18)	−0.0045 (19)	−0.0138 (18)
C23	0.086 (3)	0.076 (3)	0.070 (3)	0.012 (2)	−0.016 (2)	−0.016 (2)
C24	0.117 (4)	0.091 (4)	0.053 (2)	0.014 (3)	−0.003 (2)	−0.005 (2)
C25	0.106 (4)	0.088 (3)	0.081 (3)	0.011 (3)	0.025 (3)	−0.003 (3)
C26	0.067 (3)	0.091 (3)	0.113 (4)	0.007 (3)	0.012 (3)	−0.003 (3)
C27	0.069 (3)	0.079 (3)	0.096 (3)	0.017 (2)	−0.011 (2)	0.002 (3)

Geometric parameters (Å, º) top

O1—C9	1.244 (4)	C11—C12	1.500 (4)
O2—N3	1.218 (4)	C12—C13	1.381 (4)
O3—N3	1.217 (4)	C12—C17	1.384 (4)
O4—C19	1.313 (5)	C13—C14	1.378 (5)
O4—C20	1.473 (5)	C13—H13	0.9300
O5—C19	1.201 (4)	C14—C15	1.379 (4)
N1—C9	1.374 (4)	C14—H14	0.9300
N1—N2	1.403 (4)	C15—C16	1.361 (5)
N1—C6	1.434 (4)	C16—C17	1.384 (5)
N2—C7	1.306 (4)	C16—H16	0.9300
N3—C15	1.474 (4)	C17—H17	0.9300
N4—C11	1.326 (4)	C18—C19	1.520 (6)
N4—C18	1.452 (4)	C18—C21	1.550 (6)
N4—H4	0.8600	C18—H18	0.9800
C1—C6	1.367 (6)	C20—H20A	0.9600
C1—C2	1.376 (5)	C20—H20B	0.9600
C1—H1	0.9300	C20—H20C	0.9600
C2—C3	1.352 (8)	C21—C22	1.497 (6)
C2—H2	0.9300	C21—H21A	0.9700
C3—C4	1.365 (8)	C21—H21B	0.9700
C3—H3	0.9300	C22—C27	1.387 (6)
C4—C5	1.386 (7)	C22—C23	1.396 (6)
C4—H4A	0.9300	C23—C24	1.391 (7)
C5—C6	1.391 (6)	C23—H23	0.9300
C5—H5	0.9300	C24—C25	1.370 (7)
C7—C8	1.440 (5)	C24—H24	0.9300
C7—C10	1.494 (5)	C25—C26	1.352 (7)
C8—C11	1.385 (4)	C25—H25	0.9300
C8—C9	1.445 (4)	C26—C27	1.371 (7)
C10—H10A	0.9600	C26—H26	0.9300
C10—H10B	0.9600	C27—H27	0.9300
C10—H10C	0.9600

C19—O4—C20	116.1 (3)	C12—C13—H13	119.5
C9—N1—N2	112.5 (2)	C13—C14—C15	118.3 (3)
C9—N1—C6	129.5 (3)	C13—C14—H14	120.9
N2—N1—C6	117.7 (3)	C15—C14—H14	120.9
C7—N2—N1	106.2 (3)	C16—C15—C14	122.2 (3)
O3—N3—O2	123.6 (3)	C16—C15—N3	118.5 (3)
O3—N3—C15	118.1 (3)	C14—C15—N3	119.4 (3)
O2—N3—C15	118.2 (3)	C15—C16—C17	119.1 (3)
C11—N4—C18	127.5 (3)	C15—C16—H16	120.4
C11—N4—H4	116.3	C17—C16—H16	120.4
C18—N4—H4	116.3	C16—C17—C12	120.1 (3)
C6—C1—C2	119.6 (4)	C16—C17—H17	119.9
C6—C1—H1	120.2	C12—C17—H17	119.9
C2—C1—H1	120.2	N4—C18—C19	113.7 (3)
C3—C2—C1	121.3 (5)	N4—C18—C21	111.3 (3)
C3—C2—H2	119.3	C19—C18—C21	110.8 (3)
C1—C2—H2	119.3	N4—C18—H18	106.9
C2—C3—C4	118.7 (4)	C19—C18—H18	106.9
C2—C3—H3	120.6	C21—C18—H18	106.9
C4—C3—H3	120.6	O5—C19—O4	124.1 (4)
C3—C4—C5	122.3 (5)	O5—C19—C18	121.9 (4)
C3—C4—H4A	118.8	O4—C19—C18	114.0 (3)
C5—C4—H4A	118.8	O4—C20—H20A	109.5
C4—C5—C6	117.3 (5)	O4—C20—H20B	109.5
C4—C5—H5	121.4	H20A—C20—H20B	109.5
C6—C5—H5	121.4	O4—C20—H20C	109.5
C1—C6—C5	120.7 (3)	H20A—C20—H20C	109.5
C1—C6—N1	121.1 (3)	H20B—C20—H20C	109.5
C5—C6—N1	118.1 (4)	C22—C21—C18	112.6 (3)
N2—C7—C8	111.6 (3)	C22—C21—H21A	109.1
N2—C7—C10	117.9 (3)	C18—C21—H21A	109.1
C8—C7—C10	130.4 (3)	C22—C21—H21B	109.1
C11—C8—C7	132.0 (3)	C18—C21—H21B	109.1
C11—C8—C9	122.8 (3)	H21A—C21—H21B	107.8
C7—C8—C9	105.3 (3)	C27—C22—C23	117.2 (4)
O1—C9—N1	126.9 (3)	C27—C22—C21	121.8 (4)
O1—C9—C8	128.6 (3)	C23—C22—C21	120.9 (4)
N1—C9—C8	104.4 (3)	C24—C23—C22	120.6 (4)
C7—C10—H10A	109.5	C24—C23—H23	119.7
C7—C10—H10B	109.5	C22—C23—H23	119.7
H10A—C10—H10B	109.5	C25—C24—C23	120.3 (5)
C7—C10—H10C	109.5	C25—C24—H24	119.9
H10A—C10—H10C	109.5	C23—C24—H24	119.9
H10B—C10—H10C	109.5	C26—C25—C24	119.4 (5)
N4—C11—C8	120.0 (3)	C26—C25—H25	120.3
N4—C11—C12	118.9 (3)	C24—C25—H25	120.3
C8—C11—C12	121.1 (3)	C25—C26—C27	121.4 (5)
C13—C12—C17	119.4 (3)	C25—C26—H26	119.3
C13—C12—C11	120.7 (3)	C27—C26—H26	119.3
C17—C12—C11	119.8 (3)	C26—C27—C22	121.2 (4)
C14—C13—C12	120.9 (3)	C26—C27—H27	119.4
C14—C13—H13	119.5	C22—C27—H27	119.4

C9—N1—N2—C7	−0.7 (4)	N4—C11—C12—C17	81.3 (4)
C6—N1—N2—C7	173.7 (3)	C8—C11—C12—C17	−99.0 (4)
C6—C1—C2—C3	0.3 (7)	C17—C12—C13—C14	1.0 (5)
C1—C2—C3—C4	0.3 (9)	C11—C12—C13—C14	−177.5 (3)
C2—C3—C4—C5	−1.7 (10)	C12—C13—C14—C15	−0.1 (5)
C3—C4—C5—C6	2.4 (9)	C13—C14—C15—C16	−0.7 (5)
C2—C1—C6—C5	0.5 (6)	C13—C14—C15—N3	179.3 (3)
C2—C1—C6—N1	176.6 (4)	O3—N3—C15—C16	171.5 (4)
C4—C5—C6—C1	−1.7 (7)	O2—N3—C15—C16	−7.0 (5)
C4—C5—C6—N1	−178.0 (4)	O3—N3—C15—C14	−8.5 (5)
C9—N1—C6—C1	18.5 (5)	O2—N3—C15—C14	173.0 (3)
N2—N1—C6—C1	−154.8 (3)	C14—C15—C16—C17	0.6 (6)
C9—N1—C6—C5	−165.3 (4)	N3—C15—C16—C17	−179.4 (3)
N2—N1—C6—C5	21.4 (5)	C15—C16—C17—C12	0.3 (6)
N1—N2—C7—C8	−0.2 (4)	C13—C12—C17—C16	−1.1 (5)
N1—N2—C7—C10	−178.9 (3)	C11—C12—C17—C16	177.4 (3)
N2—C7—C8—C11	−179.3 (3)	C11—N4—C18—C19	−121.9 (4)
C10—C7—C8—C11	−0.9 (7)	C11—N4—C18—C21	112.2 (4)
N2—C7—C8—C9	1.0 (4)	C20—O4—C19—O5	−3.5 (5)
C10—C7—C8—C9	179.4 (4)	C20—O4—C19—C18	177.1 (3)
N2—N1—C9—O1	179.9 (3)	N4—C18—C19—O5	170.7 (4)
C6—N1—C9—O1	6.3 (5)	C21—C18—C19—O5	−63.1 (5)
N2—N1—C9—C8	1.3 (3)	N4—C18—C19—O4	−10.0 (4)
C6—N1—C9—C8	−172.3 (3)	C21—C18—C19—O4	116.3 (4)
C11—C8—C9—O1	0.4 (5)	N4—C18—C21—C22	−64.3 (4)
C7—C8—C9—O1	−179.9 (3)	C19—C18—C21—C22	168.2 (3)
C11—C8—C9—N1	179.0 (3)	C18—C21—C22—C27	97.0 (5)
C7—C8—C9—N1	−1.3 (3)	C18—C21—C22—C23	−80.1 (5)
C18—N4—C11—C8	−176.7 (3)	C27—C22—C23—C24	−0.4 (6)
C18—N4—C11—C12	3.1 (5)	C21—C22—C23—C24	176.9 (4)
C7—C8—C11—N4	−174.9 (4)	C22—C23—C24—C25	−0.3 (7)
C9—C8—C11—N4	4.7 (5)	C23—C24—C25—C26	0.9 (7)
C7—C8—C11—C12	5.3 (5)	C24—C25—C26—C27	−0.8 (7)
C9—C8—C11—C12	−175.1 (3)	C25—C26—C27—C22	0.1 (7)
N4—C11—C12—C13	−100.2 (4)	C23—C22—C27—C26	0.5 (6)
C8—C11—C12—C13	79.5 (4)	C21—C22—C27—C26	−176.8 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···O1	0.86	2.04	2.738 (4)	138
C1—H1···O1	0.93	2.41	3.001 (4)	121
C20—H20A···O1ⁱ	0.96	2.55	3.385 (5)	145

Symmetry code: (i) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₂₇H₂₄N₄O₅
M_r	484.50
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	296
a, b, c (Å)	6.7713 (16), 8.917 (2), 20.339 (5)
β (°)	92.489 (4)
V (Å³)	1226.9 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.20 × 0.16 × 0.12

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.980, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	6305, 2315, 1855
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.106, 1.07
No. of reflections	2315
No. of parameters	327
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.15

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···O1	0.86	2.04	2.738 (4)	138
C1—H1···O1	0.93	2.41	3.001 (4)	121
C20—H20A···O1ⁱ	0.96	2.55	3.385 (5)	145.0

Symmetry code: (i) x−1, y, z.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CSD CrossRef Web of Science Google Scholar
Bruker (2007). SAINT, SADABS and APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Habibi, M. H., Mokhtari, R., Harrington, R. W. & Clegg, W. (2007). Acta Cryst. E63, o2881. Web of Science CSD CrossRef IUCr Journals Google Scholar
Harrop, T. C., Olmstead, M. M. & Mascharak, P. K. (2003). Chem. Commun. pp. 410–411. Web of Science CSD CrossRef 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
Remya, P. N., Pavithran, R. & Reddy, M. L. P. (2005). Solvent Extr. Ion Exch. 24, 5016–5022. 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
Wu, J., Deng, R. & Chen, Z. (1993). Transition Met. Chem. 18, 23–26. CrossRef CAS Web of Science Google Scholar
Xiong, G. H., Yang, Z. M. & Guo, A. L. (1993). Fine Chem. 6, 1–3. Google Scholar
Zhang, X., Zhu, H.-L., Xu, H.-Z. & Dong, M. (2005). Acta Cryst. E61, o1629–o1630. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 68| Part 4| April 2012| Page o1062

doi:10.1107/S1600536812010343

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

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

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Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

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