Methyl N-[(4-chloro­phen­yl)(3-methyl-5-oxo-1-phenyl-4,5-dihydro-1H-pyrazol-4-yl­idene)meth­yl]glycinate

Zhang, X.; Huang, M.; Du, C.; Chen, D.

doi:10.1107/S1600536809027858

organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Pages o1951-o1952

doi:10.1107/S1600536809027858

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Methyl N-[(4-chlorophenyl)(3-methyl-5-oxo-1-phenyl-4,5-dihydro-1H-pyrazol-4-ylidene)methyl]glycinate

Xin Zhang,^a ^* Meng Huang,^a Cong Du ^a and Dan Chen ^a

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

(Received 10 July 2009; accepted 15 July 2009; online 22 July 2009)

The title compound, C₂₀H₁₈ClN₃O₃, is in an enamine–keto form, stabilized by two strong intramolecular N—H⋯O hydrogen bonds. The pyrazole ring is oriented at dihedral angles of 4.13 (3) and 85.60 (3)° with respect to the aromatic rings. The dihedral angle between the aromatic rings is 81.79 (3)°. In the crystal structure, intermolecular C—H⋯O hydrogen bonds link the molecules into double chains, which are further linked by weak C—H⋯π interactions, forming a two-dimensional network.

Related literature

For general background to Schiff base compounds in coordination chemistry, catalysis and enzymatic reactions, magnetism and molecular architectures, see: Habibi et al. (2007 ). For the anti-bacterial properties of Schiff bases derived from 4-acyl-5-pyrazolones and their metal complexes, see: Li et al. (1997 , 2004 ). For the anti-bacterial and biological activity of amino acid esters, see: Xiong et al. (1993 ). For related structures, see: Pettinari et al. (1994 ); Wang et al. (2003 ); Zhang et al. (2005 ); Zhu et al. (2005 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₂₀H₁₈ClN₃O₃
M_r = 383.82
Triclinic, $[P \overline 1]$
a = 9.309 (4) Å
b = 10.222 (4) Å
c = 10.685 (5) Å
α = 86.275 (8)°
β = 82.772 (8)°
γ = 71.749 (5)°
V = 957.6 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 296 K
0.24 × 0.20 × 0.18 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.947, T_max = 0.960
4927 measured reflections
3364 independent reflections
1975 reflections with I > 2σ(I)
R_int = 0.019

Refinement

R[F² > 2σ(F²)] = 0.075
wR(F²) = 0.229
S = 1.05
3364 reflections
246 parameters
H-atom parameters constrained
Δρ_max = 0.54 e Å⁻³
Δρ_min = −0.44 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	2.06	2.755 (4)	138
N3—H3⋯O2	0.86	2.29	2.679 (4)	108
C16—H16⋯O1ⁱ	0.93	2.42	3.287 (5)	155
C17—H17⋯O1ⁱⁱ	0.93	2.54	3.359 (4)	147
C20—H20B⋯Cg3ⁱⁱⁱ	0.96	2.69	3.604 (4)	160
Symmetry codes: (i) x-1, y, z; (ii) -x, -y+1, -z+2; (iii) -x, -y, -z+2. Cg3 is the centroid of the C12–C17 ring.

Data collection: APEX2 (Bruker, 2003 ); cell refinement: SAINT (Bruker, 2001 ); 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) and DIAMOND (Brandenburg & Berndt, 1999 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809027858/hk2736sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809027858/hk2736Isup2.hkl

checkCIF report

Comment top

Schiff base compounds play an important role in the development of coordination chemistry related to catalysis and enzymatic reactions, magnetism, and molecular architectures [Habibi et al., 2007]. In recent years, 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]. Amino acid esters also possess good antibacterial and biological activations [Xiong et al., 1993]. 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., 2005]. We report herein the crystal structure of the title compound, (I).

In the molecule of the title compound, (I), (Fig. 1) the bond lengths (Allen et al., 1987) and angles are within normal ranges. Rings A (C1-C6), B (N1/N2/C7/C9/C10) and C (C12-C17) are, of course, planar, and they are oriented at a dihedral angles of A/B = 4.13 (3), A/C = 81.79 (3) and B/C = 85.60 (3) °. Intramolecular N-H···O hydrogen bonds (Table 1) stabilize the enamine-keto form as 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, (II) (Wang et al., 2003), and result in the formations of planar five- and six-membered rings: D (O2/N3/C18/C19/H3) and E (O1/N3/C9-C11/H3), in which the dihedral angle between them is D/E = 3.83 (4)°. Ring D is oriented with respect to the adjacent ring B at a dihedral angle of 3.12 (4)°. The dihedral angle between ring B and planar (O1/N3/C9-C11) moiety is 0.94 (3)°, which is reported as 3.56 (3)° in (II).

In the crystal structure, intermolecular C-H···O hydrogen bonds (Table 1) link the molecules into double chains (Fig. 2), in which they are further linked by weak C—H···π interactions (Table 1) to form a two-dimensional network (Fig. 3), in which they may be effective in the stabilization of the structure.

Related literature top

For general background to Schiff base compounds in coordination chemistry, catalysis and enzymatic reactions, magnetism and molecular architectures, see: Habibi et al. (2007). For the antibacteri al properties of Schiff bases derived from 4-acyl-5-pyrazolones 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: Pettinari et al. (1994); Wang et al. (2003); Zhang et al. (2005); Zhu et al. (2005). For bond-length data, see: Allen et al. (1987). Cg3 is the centroid of the C12–C17 ring.

Experimental top

The title compound was synthesized by refluxing a mixture of 1-phenyl-3-methyl-4-(p-chlor-benzyl)-5-pyrazolone (15 mmol) (Pettinari et al., 1994) and glycine methyl ester (15 mmol) in ethanol (100 ml) over a steam bath for about 5 h. The product was recrystallized from ethanol, affording pale yellow crystals suitable for X-ray analysis. Analysis calculated for C₂₀H₁₈ClN₃O_3:C 62.58, H 4.73, N 10.95%; found: C 62.55, H 4.70, N 10.91%.

Computing details top

Data collection: APEX2 (Bruker, 2003); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg & Berndt, 1999); 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. Hydrogen bonds are shown as dashed lines.
	Fig. 2. The one-dimensional plane formed by the intermolecular C–H···O hydrogen bonds.
	Fig. 3. The two-dimensional network produced by the intermolecular C–H···π interactions.

Methyl N-[(4-chlorophenyl)(3-methyl-5-oxo-1-phenyl-4,5-dihydro- 1H-pyrazol-4-ylidene)methyl]glycinate top

Crystal data top

C₂₀H₁₈ClN₃O₃	Z = 2
M_r = 383.82	F(000) = 400
Triclinic, P1	D_x = 1.331 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.309 (4) Å	Cell parameters from 1323 reflections
b = 10.222 (4) Å	θ = 2.3–25.9°
c = 10.685 (5) Å	µ = 0.23 mm⁻¹
α = 86.275 (8)°	T = 296 K
β = 82.772 (8)°	Block, colorless
γ = 71.749 (5)°	0.24 × 0.20 × 0.18 mm
V = 957.6 (7) Å³

Data collection top

Bruker APEXII CCD area-detector diffractometer	3364 independent reflections
Radiation source: fine-focus sealed tube	1975 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→10
T_min = 0.947, T_max = 0.960	k = −11→12
4927 measured reflections	l = −11→12

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)] = 0.075	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.229	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.1339P)²] where P = (F_o² + 2F_c²)/3
3364 reflections	(Δ/σ)_max < 0.001
246 parameters	Δρ_max = 0.54 e Å⁻³
0 restraints	Δρ_min = −0.44 e Å⁻³

Crystal data top

C₂₀H₁₈ClN₃O₃	γ = 71.749 (5)°
M_r = 383.82	V = 957.6 (7) Å³
Triclinic, P1	Z = 2
a = 9.309 (4) Å	Mo Kα radiation
b = 10.222 (4) Å	µ = 0.23 mm⁻¹
c = 10.685 (5) Å	T = 296 K
α = 86.275 (8)°	0.24 × 0.20 × 0.18 mm
β = 82.772 (8)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	3364 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1975 reflections with I > 2σ(I)
T_min = 0.947, T_max = 0.960	R_int = 0.019
4927 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.075	0 restraints
wR(F²) = 0.229	H-atom parameters constrained
S = 1.05	Δρ_max = 0.54 e Å⁻³
3364 reflections	Δρ_min = −0.44 e Å⁻³
246 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
Cl1	−0.55778 (16)	0.32750 (16)	0.61403 (15)	0.1056 (6)
O1	0.2121 (3)	0.5392 (3)	0.8771 (2)	0.0536 (7)
O2	0.2655 (4)	0.1981 (3)	1.0279 (3)	0.0771 (9)
O3	0.1496 (3)	0.0367 (3)	1.0650 (3)	0.0716 (9)
N1	0.1065 (3)	0.7252 (3)	0.7427 (3)	0.0520 (8)
N2	−0.0161 (4)	0.7657 (3)	0.6679 (3)	0.0573 (9)
N3	0.0591 (3)	0.3478 (3)	0.8789 (3)	0.0510 (8)
H3	0.1341	0.3706	0.8998	0.061*
C1	0.3191 (5)	0.7807 (4)	0.8132 (4)	0.0666 (12)
H1	0.3399	0.7016	0.8647	0.080*
C2	0.4086 (5)	0.8654 (5)	0.8087 (5)	0.0801 (14)
H2	0.4895	0.8424	0.8574	0.096*
C3	0.3824 (6)	0.9811 (6)	0.7354 (6)	0.0890 (15)
H3A	0.4449	1.0368	0.7327	0.107*
C4	0.2603 (7)	1.0159 (5)	0.6639 (5)	0.0880 (15)
H4	0.2405	1.0960	0.6138	0.106*
C5	0.1672 (5)	0.9319 (5)	0.6663 (4)	0.0697 (12)
H5	0.0855	0.9552	0.6184	0.084*
C6	0.1992 (4)	0.8118 (4)	0.7424 (3)	0.0525 (9)
C7	−0.0797 (4)	0.6684 (4)	0.6807 (3)	0.0526 (10)
C8	−0.2151 (5)	0.6816 (5)	0.6135 (4)	0.0776 (14)
H8A	−0.2512	0.7733	0.5784	0.116*
H8B	−0.2942	0.6634	0.6720	0.116*
H8C	−0.1870	0.6165	0.5470	0.116*
C9	−0.0021 (4)	0.5568 (4)	0.7624 (3)	0.0458 (9)
C10	0.1185 (4)	0.5995 (4)	0.8021 (3)	0.0450 (8)
C11	−0.0299 (4)	0.4347 (4)	0.8029 (3)	0.0432 (8)
C12	−0.1577 (4)	0.3973 (4)	0.7612 (3)	0.0454 (9)
C13	−0.1405 (5)	0.3365 (5)	0.6462 (4)	0.0683 (12)
H13	−0.0457	0.3108	0.5986	0.082*
C14	−0.2631 (6)	0.3136 (5)	0.6015 (4)	0.0770 (14)
H14	−0.2513	0.2720	0.5244	0.092*
C15	−0.4031 (5)	0.3528 (4)	0.6722 (4)	0.0591 (11)
C16	−0.4215 (4)	0.4092 (4)	0.7886 (4)	0.0604 (11)
H16	−0.5155	0.4314	0.8373	0.072*
C17	−0.2987 (4)	0.4323 (4)	0.8322 (3)	0.0526 (10)
H17	−0.3107	0.4719	0.9103	0.063*
C18	0.0428 (4)	0.2179 (4)	0.9305 (4)	0.0545 (10)
H18A	0.0493	0.1573	0.8625	0.065*
H18B	−0.0560	0.2336	0.9794	0.065*
C19	0.1662 (4)	0.1521 (4)	1.0130 (4)	0.0561 (10)
C20	0.2628 (6)	−0.0381 (5)	1.1457 (5)	0.0911 (16)
H20A	0.3615	−0.0631	1.0979	0.137*
H20B	0.2404	−0.1199	1.1791	0.137*
H20C	0.2620	0.0188	1.2140	0.137*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0921 (10)	0.1261 (12)	0.1282 (12)	−0.0573 (9)	−0.0643 (9)	0.0046 (9)
O1	0.0457 (14)	0.0636 (16)	0.0557 (15)	−0.0186 (12)	−0.0205 (12)	0.0069 (13)
O2	0.0713 (19)	0.075 (2)	0.098 (2)	−0.0316 (17)	−0.0458 (17)	0.0202 (17)
O3	0.0718 (19)	0.0580 (18)	0.091 (2)	−0.0220 (15)	−0.0336 (16)	0.0132 (16)
N1	0.0506 (18)	0.058 (2)	0.0516 (18)	−0.0206 (15)	−0.0159 (14)	0.0053 (15)
N2	0.0513 (18)	0.068 (2)	0.0531 (19)	−0.0161 (17)	−0.0172 (15)	0.0106 (16)
N3	0.0406 (16)	0.059 (2)	0.0574 (18)	−0.0180 (14)	−0.0197 (14)	0.0065 (16)
C1	0.060 (3)	0.066 (3)	0.080 (3)	−0.025 (2)	−0.021 (2)	0.006 (2)
C2	0.066 (3)	0.080 (3)	0.104 (4)	−0.032 (3)	−0.022 (3)	−0.001 (3)
C3	0.091 (4)	0.077 (3)	0.110 (4)	−0.044 (3)	−0.012 (3)	0.007 (3)
C4	0.107 (4)	0.074 (3)	0.089 (4)	−0.040 (3)	−0.016 (3)	0.024 (3)
C5	0.078 (3)	0.067 (3)	0.064 (3)	−0.022 (2)	−0.018 (2)	0.010 (2)
C6	0.054 (2)	0.055 (2)	0.049 (2)	−0.0177 (19)	−0.0023 (17)	−0.0072 (18)
C7	0.046 (2)	0.068 (3)	0.045 (2)	−0.018 (2)	−0.0144 (17)	0.0054 (19)
C8	0.067 (3)	0.101 (4)	0.074 (3)	−0.033 (3)	−0.038 (2)	0.031 (3)
C9	0.0382 (19)	0.061 (2)	0.0395 (18)	−0.0157 (17)	−0.0096 (15)	0.0030 (17)
C10	0.0407 (19)	0.052 (2)	0.0415 (19)	−0.0110 (16)	−0.0096 (15)	−0.0003 (17)
C11	0.0347 (17)	0.057 (2)	0.0381 (18)	−0.0138 (16)	−0.0038 (14)	−0.0054 (16)
C12	0.0424 (19)	0.055 (2)	0.0407 (18)	−0.0156 (17)	−0.0115 (15)	−0.0021 (16)
C13	0.058 (3)	0.098 (4)	0.052 (2)	−0.027 (2)	−0.0022 (19)	−0.022 (2)
C14	0.086 (3)	0.101 (4)	0.057 (3)	−0.038 (3)	−0.020 (2)	−0.020 (2)
C15	0.060 (3)	0.064 (3)	0.063 (3)	−0.026 (2)	−0.032 (2)	0.008 (2)
C16	0.042 (2)	0.071 (3)	0.069 (3)	−0.0180 (19)	−0.0127 (18)	−0.001 (2)
C17	0.040 (2)	0.068 (2)	0.049 (2)	−0.0129 (18)	−0.0076 (16)	−0.0108 (19)
C18	0.054 (2)	0.056 (2)	0.060 (2)	−0.0224 (19)	−0.0170 (19)	0.0012 (19)
C19	0.054 (2)	0.053 (2)	0.064 (3)	−0.017 (2)	−0.0137 (19)	−0.004 (2)
C20	0.093 (4)	0.068 (3)	0.111 (4)	−0.013 (3)	−0.053 (3)	0.027 (3)

Geometric parameters (Å, º) top

Cl1—C15	1.734 (4)	C7—C8	1.494 (5)
O1—C10	1.248 (4)	C8—H8A	0.9600
O2—C19	1.191 (4)	C8—H8B	0.9600
O3—C19	1.316 (5)	C8—H8C	0.9600
O3—C20	1.442 (5)	C9—C11	1.384 (5)
N1—C10	1.374 (5)	C9—C10	1.443 (5)
N1—C6	1.416 (5)	C11—C12	1.484 (5)
N1—N2	1.416 (4)	C12—C13	1.382 (5)
N2—C7	1.300 (5)	C12—C17	1.385 (5)
N3—C11	1.323 (4)	C13—C14	1.380 (6)
N3—C18	1.449 (5)	C13—H13	0.9300
N3—H3	0.8600	C14—C15	1.376 (6)
C1—C6	1.371 (5)	C14—H14	0.9300
C1—C2	1.372 (6)	C15—C16	1.373 (6)
C1—H1	0.9300	C16—C17	1.377 (5)
C2—C3	1.349 (7)	C16—H16	0.9300
C2—H2	0.9300	C17—H17	0.9300
C3—C4	1.389 (7)	C18—C19	1.498 (5)
C3—H3A	0.9300	C18—H18A	0.9700
C4—C5	1.396 (7)	C18—H18B	0.9700
C4—H4	0.9300	C20—H20A	0.9600
C5—C6	1.399 (6)	C20—H20B	0.9600
C5—H5	0.9300	C20—H20C	0.9600
C7—C9	1.449 (5)

C19—O3—C20	115.9 (3)	O1—C10—C9	128.3 (3)
C10—N1—C6	130.1 (3)	N1—C10—C9	105.4 (3)
C10—N1—N2	111.5 (3)	N3—C11—C9	120.2 (3)
C6—N1—N2	118.3 (3)	N3—C11—C12	118.5 (3)
C7—N2—N1	106.7 (3)	C9—C11—C12	121.2 (3)
C11—N3—C18	126.5 (3)	C13—C12—C17	119.2 (3)
C11—N3—H3	116.8	C13—C12—C11	120.2 (3)
C18—N3—H3	116.8	C17—C12—C11	120.5 (3)
C6—C1—C2	120.5 (4)	C14—C13—C12	120.4 (4)
C6—C1—H1	119.7	C14—C13—H13	119.8
C2—C1—H1	119.7	C12—C13—H13	119.8
C3—C2—C1	121.7 (5)	C15—C14—C13	119.4 (4)
C3—C2—H2	119.2	C15—C14—H14	120.3
C1—C2—H2	119.2	C13—C14—H14	120.3
C2—C3—C4	118.9 (5)	C16—C15—C14	121.1 (4)
C2—C3—H3A	120.5	C16—C15—Cl1	119.6 (3)
C4—C3—H3A	120.5	C14—C15—Cl1	119.2 (3)
C3—C4—C5	120.8 (5)	C15—C16—C17	119.1 (4)
C3—C4—H4	119.6	C15—C16—H16	120.5
C5—C4—H4	119.6	C17—C16—H16	120.5
C4—C5—C6	118.6 (4)	C16—C17—C12	120.8 (3)
C4—C5—H5	120.7	C16—C17—H17	119.6
C6—C5—H5	120.7	C12—C17—H17	119.6
C1—C6—C5	119.5 (4)	N3—C18—C19	109.4 (3)
C1—C6—N1	122.0 (4)	N3—C18—H18A	109.8
C5—C6—N1	118.5 (4)	C19—C18—H18A	109.8
N2—C7—C9	111.6 (3)	N3—C18—H18B	109.8
N2—C7—C8	119.7 (3)	C19—C18—H18B	109.8
C9—C7—C8	128.7 (4)	H18A—C18—H18B	108.2
C7—C8—H8A	109.5	O2—C19—O3	125.3 (4)
C7—C8—H8B	109.5	O2—C19—C18	124.3 (4)
H8A—C8—H8B	109.5	O3—C19—C18	110.3 (3)
C7—C8—H8C	109.5	O3—C20—H20A	109.5
H8A—C8—H8C	109.5	O3—C20—H20B	109.5
H8B—C8—H8C	109.5	H20A—C20—H20B	109.5
C11—C9—C10	123.5 (3)	O3—C20—H20C	109.5
C11—C9—C7	131.6 (3)	H20A—C20—H20C	109.5
C10—C9—C7	104.9 (3)	H20B—C20—H20C	109.5
O1—C10—N1	126.3 (3)

C10—N1—N2—C7	0.4 (4)	C7—C9—C10—N1	−1.0 (4)
C6—N1—N2—C7	177.9 (3)	C18—N3—C11—C9	178.9 (3)
C6—C1—C2—C3	0.0 (7)	C18—N3—C11—C12	−2.0 (5)
C1—C2—C3—C4	0.7 (8)	C10—C9—C11—N3	−2.2 (5)
C2—C3—C4—C5	−0.8 (8)	C7—C9—C11—N3	180.0 (4)
C3—C4—C5—C6	0.0 (7)	C10—C9—C11—C12	178.7 (3)
C2—C1—C6—C5	−0.8 (6)	C7—C9—C11—C12	0.8 (6)
C2—C1—C6—N1	178.6 (4)	N3—C11—C12—C13	−96.3 (4)
C4—C5—C6—C1	0.8 (6)	C9—C11—C12—C13	82.8 (5)
C4—C5—C6—N1	−178.7 (4)	N3—C11—C12—C17	88.6 (4)
C10—N1—C6—C1	−3.6 (6)	C9—C11—C12—C17	−92.2 (4)
N2—N1—C6—C1	179.3 (3)	C17—C12—C13—C14	1.4 (7)
C10—N1—C6—C5	175.8 (4)	C11—C12—C13—C14	−173.8 (4)
N2—N1—C6—C5	−1.2 (5)	C12—C13—C14—C15	0.5 (7)
N1—N2—C7—C9	−1.0 (4)	C13—C14—C15—C16	−2.7 (7)
N1—N2—C7—C8	179.4 (3)	C13—C14—C15—Cl1	178.5 (4)
N2—C7—C9—C11	179.4 (4)	C14—C15—C16—C17	3.0 (6)
C8—C7—C9—C11	−1.0 (7)	Cl1—C15—C16—C17	−178.2 (3)
N2—C7—C9—C10	1.3 (4)	C15—C16—C17—C12	−1.1 (6)
C8—C7—C9—C10	−179.2 (4)	C13—C12—C17—C16	−1.0 (6)
C6—N1—C10—O1	5.2 (6)	C11—C12—C17—C16	174.1 (4)
N2—N1—C10—O1	−177.6 (3)	C11—N3—C18—C19	−179.5 (3)
C6—N1—C10—C9	−176.7 (3)	C20—O3—C19—O2	−0.2 (6)
N2—N1—C10—C9	0.5 (4)	C20—O3—C19—C18	179.2 (4)
C11—C9—C10—O1	−1.3 (6)	N3—C18—C19—O2	−3.2 (6)
C7—C9—C10—O1	177.0 (3)	N3—C18—C19—O3	177.4 (3)
C11—C9—C10—N1	−179.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O1	0.86	2.06	2.755 (4)	138
N3—H3···O2	0.86	2.29	2.679 (4)	108
C16—H16···O1ⁱ	0.93	2.42	3.287 (5)	155
C17—H17···O1ⁱⁱ	0.93	2.54	3.359 (4)	147
C20—H20B···Cg3ⁱⁱⁱ	0.96	2.69	3.604 (4)	160

Symmetry codes: (i) x−1, y, z; (ii) −x, −y+1, −z+2; (iii) −x, −y, −z+2.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₈ClN₃O₃
M_r	383.82
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	9.309 (4), 10.222 (4), 10.685 (5)
α, β, γ (°)	86.275 (8), 82.772 (8), 71.749 (5)
V (Å³)	957.6 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.24 × 0.20 × 0.18

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.947, 0.960
No. of measured, independent and observed [I > 2σ(I)] reflections	4927, 3364, 1975
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.075, 0.229, 1.05
No. of reflections	3364
No. of parameters	246
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.54, −0.44

Computer programs: APEX2 (Bruker, 2003), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg & Berndt, 1999), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O1	0.86	2.06	2.755 (4)	137.5
N3—H3···O2	0.86	2.29	2.679 (4)	107.8
C16—H16···O1ⁱ	0.93	2.42	3.287 (5)	154.9
C17—H17···O1ⁱⁱ	0.93	2.54	3.359 (4)	147.3
C20—H20B···Cg3ⁱⁱⁱ	0.96	2.69	3.604 (4)	160

Symmetry codes: (i) x−1, y, z; (ii) −x, −y+1, −z+2; (iii) −x, −y, −z+2.

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. CrossRef Web of Science Google Scholar
Brandenburg, K. & Berndt, M. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2001). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2003). 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
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Li, J. Z., Yu, W. J. & Du, X. Y. (1997). Chin. J. Appl. Chem. 14, 98–100. CAS Google Scholar
Pettinari, C., Marchetti, F. & Augusto, C. (1994). Polyhedron, 13, 939–950. CSD CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (1996). 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
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Volume 65| Part 8| August 2009| Pages o1951-o1952

doi:10.1107/S1600536809027858

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

Methyl N-[(4-chloro­phen­yl)(3-methyl-5-oxo-1-phenyl-4,5-di­hydro-1H-pyrazol-4-yl­­idene)meth­yl]glycinate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

Methyl N-[(4-chlorophenyl)(3-methyl-5-oxo-1-phenyl-4,5-dihydro-1H-pyrazol-4-ylidene)methyl]glycinate