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

Han, X.; Yang, X.-D.; Dai, X.-C.

doi:10.1107/S1600536811026158

organic compounds

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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o1936

doi:10.1107/S1600536811026158

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

Xiao Han,^a ^* Xiao-Dong Yang ^a and Xiao-Chang Dai ^a

^aSchool of Chemical Science and Technology, Yunnan University, Kunming 65009, People's Republic of China
^*Correspondence e-mail: blackcrossing630@vip.sina.com

(Received 19 June 2011; accepted 1 July 2011; online 6 July 2011)

In the title compound, C₁₈H₁₇N₃O₄, the amino group of the glycine methyl ester fragment is involved in an intramolecular N—H⋯O hydrogen bond. The phenyl and furyl rings form dihedral angles of 10.20 (4) and 54.56°, respectively, with the pyrazole ring. In the crystal, molecules related by translation along the b axis are linked into chains via weak intermolecular C—H⋯O hydrogen bonds.

Related literature

For a related structure, see: Zhang et al. (2007 ). For details of the synthesis, see: Jensen (1959 ). For applications of pyrazolone derivatives in coordination chemistry, see: Casas et al. (2007 ). For the antibacterial activity of pyrazolone derivatives, see: Li et al. (2000 ); Zhang et al. (2008 ).

Experimental

Crystal data

C₁₈H₁₇N₃O₄
M_r = 339.35
Triclinic, $[P \overline 1]$
a = 7.499 (4) Å
b = 9.503 (5) Å
c = 11.749 (6) Å
α = 96.712 (7)°
β = 91.654 (8)°
γ = 90.337 (7)°
V = 831.2 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 295 K
0.48 × 0.14 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer
6492 measured reflections
2915 independent reflections
1805 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.150
S = 1.01
29015 reflections
232 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O1	0.97 (3)	1.89 (3)	2.704 (3)	140 (2)
C14—H14⋯O1ⁱ	0.93	2.48	3.386 (4)	164
Symmetry code: (i) x, y-1, z.

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT-Plus (Bruker, 2005); 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/S1600536811026158/cv5123sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811026158/cv5123Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811026158/cv5123Isup3.cml

checkCIF report

Comment top

Pyrazolones constitute an important class of heterocycles due to their properties and applications (Casas et al., 2007). Schiff bases derived from 1-phenyl-3-methyl-4-(2-furoyl)-5-pyrazolone (PMFP) have found extensive application in coordination chemistry and due to their antibacterial activity (Zhang et al., 2007, 2008; Li et al., 2000). In order to expand this field, we present here the title compound (I).

In (I) (Fig. 1), the phenyl ring (C1-C6) is twisted at 10.20 (4)° from the mean plane of pyrazole ring. The pyrazole ring and the O1/C10/C9/C11/N3 mean form a dihedral angle of 5.62 (4)°. The bond length of C9—C11(1.390 (3) Å) between the usual C—C and C=C bonds indicates the delocalization of the electrons. Strong intramolecular hydrogen bond N3—H3A···O1(Table 1) is indicative of the enamine-keto form.

In the crystal structure, molecules related by translation along axis b are linked into chains via weak intermolecular C—H···O hydrogen bonds.

Related literature top

For a related structure, see: Zhang et al. (2007). For details of the synthesis, see: Jensen (1959). For applications of pyrazolone derivatives in coordination chemistry, see: Casas et al. (2007). For the antibacterial activity of pyrazolone derivatives, see: Li et al. (2000); Zhang et al. (2008).

Experimental top

PMFP was synthesized according to the method proposed by Jensen (1959). A mixture of a 10 ml PMFP (2 mmol, 0.5366 g) anhydrous ethanol solution, and 10 ml Glycine methyl ester hydrochloride anhydrous ethanol solution (2 mmol, 0.2511 g)solution was refluxed for ca.7 h, adding a few drops of glacial acetic acid as a catalyst. Then ethanol was removed by evaporation and the resulting black precipitate formed was filtered off, washed with cold anhydrous ethanol and dried in air. Black block single crystals suitable for analysis were obtained by slowly evaporation of a solution in anhydrous ethanol at room temperature for a few days.

Computing details top

Data collection: APEX2 (Bruker, 200); cell refinement: SAINT-Plus (Bruker, 2005); data reduction: SAINT-Plus (Bruker, 2005); 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. Dotted line indicates hydrogen bond.

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

Crystal data top

C₁₈H₁₇N₃O₄	Z = 2
M_r = 339.35	F(000) = 356
Triclinic, P1	D_x = 1.356 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.499 (4) Å	Cell parameters from 1502 reflections
b = 9.503 (5) Å	θ = 2.9–22.6°
c = 11.749 (6) Å	µ = 0.10 mm⁻¹
α = 96.712 (7)°	T = 295 K
β = 91.654 (8)°	Block, black
γ = 90.337 (7)°	0.48 × 0.14 × 0.08 mm
V = 831.2 (7) Å³

Data collection top

Bruker APEXII CCD diffractometer	1805 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.034
Graphite monochromator	θ_max = 25.0°, θ_min = 2.6°
phi and ω scans	h = −8→8
6492 measured reflections	k = −11→11
2915 independent reflections	l = −13→13

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.150	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.0826P)²] where P = (F_o² + 2F_c²)/3
2915 reflections	(Δ/σ)_max < 0.001
232 parameters	Δρ_max = 0.17 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₁₈H₁₇N₃O₄	γ = 90.337 (7)°
M_r = 339.35	V = 831.2 (7) Å³
Triclinic, P1	Z = 2
a = 7.499 (4) Å	Mo Kα radiation
b = 9.503 (5) Å	µ = 0.10 mm⁻¹
c = 11.749 (6) Å	T = 295 K
α = 96.712 (7)°	0.48 × 0.14 × 0.08 mm
β = 91.654 (8)°

Data collection top

Bruker APEXII CCD diffractometer	1805 reflections with I > 2σ(I)
6492 measured reflections	R_int = 0.034
2915 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.150	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.17 e Å⁻³
2915 reflections	Δρ_min = −0.21 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	0.2043 (3)	0.1986 (3)	0.7105 (2)	0.0509 (6)
C2	0.1118 (4)	0.1820 (3)	0.6063 (3)	0.0697 (8)
H2	0.0454	0.1000	0.5838	0.084*
C3	0.1192 (5)	0.2881 (4)	0.5362 (3)	0.0888 (10)
H3	0.0555	0.2778	0.4666	0.107*
C4	0.2192 (5)	0.4093 (4)	0.5672 (3)	0.0848 (10)
H4	0.2235	0.4799	0.5188	0.102*
C5	0.3120 (4)	0.4247 (3)	0.6696 (3)	0.0725 (8)
H5	0.3797	0.5064	0.6909	0.087*
C6	0.3064 (4)	0.3203 (3)	0.7418 (2)	0.0599 (7)
H6	0.3707	0.3313	0.8112	0.072*
C7	0.0294 (4)	−0.2611 (3)	0.8061 (2)	0.0648 (8)
H7A	−0.0553	−0.2639	0.7430	0.097*
H7B	−0.0311	−0.2784	0.8741	0.097*
H7C	0.1178	−0.3325	0.7892	0.097*
C8	0.1184 (3)	−0.1175 (2)	0.8250 (2)	0.0493 (6)
C9	0.2063 (3)	−0.0467 (2)	0.9256 (2)	0.0446 (6)
C10	0.2473 (3)	0.0934 (2)	0.8965 (2)	0.0464 (6)
C11	0.2438 (3)	−0.0855 (2)	1.0341 (2)	0.0461 (6)
C12	0.2315 (3)	−0.2330 (2)	1.0582 (2)	0.0507 (6)
C13	0.2946 (3)	−0.3534 (2)	1.0035 (2)	0.0605 (7)
H13	0.3546	−0.3628	0.9349	0.073*
C14	0.2530 (4)	−0.4631 (3)	1.0695 (3)	0.0741 (9)
H14	0.2804	−0.5585	1.0534	0.089*
C15	0.1673 (4)	−0.4029 (3)	1.1587 (3)	0.0827 (10)
H15	0.1234	−0.4516	1.2163	0.099*
C16	0.6100 (4)	0.1991 (3)	1.4644 (3)	0.0859 (10)
H16A	0.7236	0.2106	1.4309	0.129*
H16B	0.6277	0.1728	1.5403	0.129*
H16C	0.5461	0.2867	1.4681	0.129*
C17	0.4484 (3)	0.1167 (3)	1.2930 (2)	0.0533 (6)
C18	0.3474 (3)	−0.0089 (2)	1.2339 (2)	0.0538 (7)
H18A	0.4205	−0.0928	1.2334	0.065*
H18B	0.2405	−0.0242	1.2756	0.065*
H3A	0.309 (3)	0.107 (3)	1.094 (2)	0.065 (8)*
N1	0.1955 (2)	0.09022 (19)	0.78289 (18)	0.0501 (5)
N2	0.1101 (3)	−0.0388 (2)	0.74126 (18)	0.0540 (6)
N3	0.2991 (3)	0.0135 (2)	1.11800 (17)	0.0498 (5)
O1	0.3157 (2)	0.19626 (16)	0.95855 (14)	0.0587 (5)
O2	0.1511 (3)	−0.26029 (18)	1.15579 (17)	0.0717 (6)
O3	0.4695 (3)	0.22735 (19)	1.25441 (17)	0.0740 (6)
O4	0.5077 (2)	0.08888 (19)	1.39454 (17)	0.0684 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0540 (14)	0.0451 (14)	0.0541 (16)	0.0075 (11)	0.0107 (12)	0.0048 (12)
C2	0.0727 (18)	0.0695 (19)	0.067 (2)	−0.0029 (15)	−0.0007 (16)	0.0103 (16)
C3	0.099 (2)	0.098 (3)	0.073 (2)	0.001 (2)	−0.0079 (19)	0.029 (2)
C4	0.103 (2)	0.071 (2)	0.086 (3)	0.0040 (19)	0.010 (2)	0.0325 (19)
C5	0.090 (2)	0.0497 (17)	0.079 (2)	0.0030 (15)	0.0129 (18)	0.0110 (15)
C6	0.0764 (18)	0.0431 (15)	0.0602 (17)	0.0008 (13)	0.0075 (14)	0.0051 (13)
C7	0.0724 (17)	0.0433 (15)	0.0753 (19)	−0.0130 (13)	0.0006 (15)	−0.0057 (13)
C8	0.0486 (14)	0.0396 (13)	0.0582 (16)	0.0015 (11)	0.0102 (12)	−0.0031 (13)
C9	0.0488 (13)	0.0317 (12)	0.0516 (15)	0.0004 (10)	0.0073 (11)	−0.0037 (11)
C10	0.0476 (13)	0.0376 (13)	0.0523 (16)	0.0022 (10)	0.0064 (11)	−0.0037 (11)
C11	0.0430 (13)	0.0352 (13)	0.0589 (16)	0.0015 (10)	0.0111 (11)	−0.0029 (12)
C12	0.0510 (14)	0.0375 (13)	0.0633 (16)	−0.0027 (11)	0.0126 (12)	0.0017 (11)
C13	0.0667 (16)	0.0362 (14)	0.0769 (18)	0.0007 (12)	0.0145 (14)	−0.0040 (13)
C14	0.080 (2)	0.0348 (15)	0.107 (2)	0.0035 (13)	0.0123 (18)	0.0032 (15)
C15	0.107 (2)	0.0366 (16)	0.107 (3)	−0.0150 (15)	0.020 (2)	0.0167 (16)
C16	0.093 (2)	0.090 (2)	0.068 (2)	−0.0136 (19)	−0.0048 (17)	−0.0150 (18)
C17	0.0572 (15)	0.0503 (16)	0.0520 (17)	0.0034 (12)	0.0090 (13)	0.0026 (13)
C18	0.0562 (15)	0.0431 (14)	0.0618 (18)	−0.0002 (11)	0.0050 (13)	0.0046 (12)
N1	0.0560 (12)	0.0388 (11)	0.0533 (13)	−0.0014 (9)	0.0035 (10)	−0.0036 (10)
N2	0.0573 (13)	0.0410 (12)	0.0612 (14)	−0.0026 (9)	0.0054 (10)	−0.0052 (11)
N3	0.0633 (13)	0.0348 (11)	0.0507 (13)	0.0006 (9)	0.0020 (10)	0.0025 (10)
O1	0.0786 (12)	0.0353 (9)	0.0598 (11)	−0.0064 (8)	−0.0016 (9)	−0.0035 (8)
O2	0.0906 (13)	0.0409 (10)	0.0846 (14)	−0.0075 (9)	0.0310 (11)	0.0049 (9)
O3	0.0962 (14)	0.0482 (12)	0.0768 (14)	−0.0107 (10)	−0.0018 (11)	0.0063 (10)
O4	0.0828 (13)	0.0657 (13)	0.0548 (12)	−0.0119 (10)	−0.0029 (10)	0.0016 (10)

Geometric parameters (Å, º) top

C1—C2	1.382 (4)	C11—N3	1.335 (3)
C1—C6	1.390 (4)	C11—C12	1.464 (3)
C1—N1	1.412 (3)	C12—C13	1.341 (3)
C2—C3	1.377 (4)	C12—O2	1.361 (3)
C2—H2	0.9300	C13—C14	1.408 (4)
C3—C4	1.377 (5)	C13—H13	0.9300
C3—H3	0.9300	C14—C15	1.320 (4)
C4—C5	1.365 (4)	C14—H14	0.9300
C4—H4	0.9300	C15—O2	1.366 (3)
C5—C6	1.380 (4)	C15—H15	0.9300
C5—H5	0.9300	C16—O4	1.453 (3)
C6—H6	0.9300	C16—H16A	0.9600
C7—C8	1.505 (3)	C16—H16B	0.9600
C7—H7A	0.9600	C16—H16C	0.9600
C7—H7B	0.9600	C17—O3	1.204 (3)
C7—H7C	0.9600	C17—O4	1.317 (3)
C8—N2	1.303 (3)	C17—C18	1.498 (4)
C8—C9	1.431 (3)	C18—N3	1.440 (3)
C9—C11	1.390 (3)	C18—H18A	0.9700
C9—C10	1.446 (3)	C18—H18B	0.9700
C10—O1	1.247 (3)	N1—N2	1.409 (3)
C10—N1	1.377 (3)	N3—H3A	0.97 (3)

C2—C1—C6	119.7 (2)	C13—C12—O2	109.9 (2)
C2—C1—N1	119.3 (2)	C13—C12—C11	131.8 (2)
C6—C1—N1	121.1 (2)	O2—C12—C11	118.2 (2)
C3—C2—C1	119.3 (3)	C12—C13—C14	107.2 (2)
C3—C2—H2	120.4	C12—C13—H13	126.4
C1—C2—H2	120.4	C14—C13—H13	126.4
C2—C3—C4	121.2 (3)	C15—C14—C13	106.1 (2)
C2—C3—H3	119.4	C15—C14—H14	127.0
C4—C3—H3	119.4	C13—C14—H14	127.0
C5—C4—C3	119.4 (3)	C14—C15—O2	111.5 (3)
C5—C4—H4	120.3	C14—C15—H15	124.2
C3—C4—H4	120.3	O2—C15—H15	124.2
C4—C5—C6	120.6 (3)	O4—C16—H16A	109.5
C4—C5—H5	119.7	O4—C16—H16B	109.5
C6—C5—H5	119.7	H16A—C16—H16B	109.5
C5—C6—C1	119.8 (3)	O4—C16—H16C	109.5
C5—C6—H6	120.1	H16A—C16—H16C	109.5
C1—C6—H6	120.1	H16B—C16—H16C	109.5
C8—C7—H7A	109.5	O3—C17—O4	125.1 (3)
C8—C7—H7B	109.5	O3—C17—C18	125.1 (3)
H7A—C7—H7B	109.5	O4—C17—C18	109.8 (2)
C8—C7—H7C	109.5	N3—C18—C17	110.5 (2)
H7A—C7—H7C	109.5	N3—C18—H18A	109.6
H7B—C7—H7C	109.5	C17—C18—H18A	109.6
N2—C8—C9	112.3 (2)	N3—C18—H18B	109.6
N2—C8—C7	117.8 (2)	C17—C18—H18B	109.6
C9—C8—C7	129.8 (2)	H18A—C18—H18B	108.1
C11—C9—C8	133.2 (2)	C10—N1—N2	111.56 (19)
C11—C9—C10	121.9 (2)	C10—N1—C1	129.3 (2)
C8—C9—C10	104.8 (2)	N2—N1—C1	118.9 (2)
O1—C10—N1	126.3 (2)	C8—N2—N1	106.2 (2)
O1—C10—C9	128.8 (2)	C11—N3—C18	126.3 (2)
N1—C10—C9	104.9 (2)	C11—N3—H3A	113.8 (15)
N3—C11—C9	119.2 (2)	C18—N3—H3A	119.8 (15)
N3—C11—C12	118.9 (2)	C12—O2—C15	105.4 (2)
C9—C11—C12	121.9 (2)	C17—O4—C16	117.5 (2)

C6—C1—C2—C3	−1.5 (4)	C11—C12—C13—C14	176.1 (3)
N1—C1—C2—C3	179.4 (2)	C12—C13—C14—C15	0.4 (3)
C1—C2—C3—C4	1.1 (5)	C13—C14—C15—O2	−0.4 (4)
C2—C3—C4—C5	−0.4 (5)	O3—C17—C18—N3	7.8 (4)
C3—C4—C5—C6	0.0 (5)	O4—C17—C18—N3	−173.49 (19)
C4—C5—C6—C1	−0.5 (4)	O1—C10—N1—N2	−175.3 (2)
C2—C1—C6—C5	1.2 (4)	C9—C10—N1—N2	5.2 (2)
N1—C1—C6—C5	−179.7 (2)	O1—C10—N1—C1	−0.7 (4)
N2—C8—C9—C11	178.9 (2)	C9—C10—N1—C1	179.8 (2)
C7—C8—C9—C11	2.6 (4)	C2—C1—N1—C10	−166.8 (2)
N2—C8—C9—C10	2.5 (3)	C6—C1—N1—C10	14.1 (4)
C7—C8—C9—C10	−173.8 (2)	C2—C1—N1—N2	7.4 (3)
C11—C9—C10—O1	−0.9 (4)	C6—C1—N1—N2	−171.6 (2)
C8—C9—C10—O1	175.9 (2)	C9—C8—N2—N1	0.6 (2)
C11—C9—C10—N1	178.59 (19)	C7—C8—N2—N1	177.36 (19)
C8—C9—C10—N1	−4.5 (2)	C10—N1—N2—C8	−3.7 (2)
C8—C9—C11—N3	−167.5 (2)	C1—N1—N2—C8	−178.93 (18)
C10—C9—C11—N3	8.3 (3)	C9—C11—N3—C18	−178.5 (2)
C8—C9—C11—C12	15.0 (4)	C12—C11—N3—C18	−0.9 (3)
C10—C9—C11—C12	−169.2 (2)	C17—C18—N3—C11	164.5 (2)
N3—C11—C12—C13	−129.3 (3)	C13—C12—O2—C15	−0.1 (3)
C9—C11—C12—C13	48.2 (4)	C11—C12—O2—C15	−176.9 (2)
N3—C11—C12—O2	46.7 (3)	C14—C15—O2—C12	0.3 (3)
C9—C11—C12—O2	−135.8 (2)	O3—C17—O4—C16	−1.5 (4)
O2—C12—C13—C14	−0.2 (3)	C18—C17—O4—C16	179.8 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O1	0.97 (3)	1.89 (3)	2.704 (3)	140 (2)
C14—H14···O1ⁱ	0.93	2.48	3.386 (4)	164

Symmetry code: (i) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₇N₃O₄
M_r	339.35
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	7.499 (4), 9.503 (5), 11.749 (6)
α, β, γ (°)	96.712 (7), 91.654 (8), 90.337 (7)
V (Å³)	831.2 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.48 × 0.14 × 0.08

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	6492, 2915, 1805
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.150, 1.01
No. of reflections	2915
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)	0.17, −0.21

Computer programs: APEX2 (Bruker, 200), SAINT-Plus (Bruker, 2005), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O1	0.97 (3)	1.89 (3)	2.704 (3)	140 (2)
C14—H14···O1ⁱ	0.93	2.48	3.386 (4)	164

Symmetry code: (i) x, y−1, z.

Acknowledgements

The authors gratefully acknowledge financial support from the study on structure–activity relationships of helicid analogues.

References

Bruker (2005). APEX2 and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Casas, J. S., García-Tasende, M. S., Sanchez, A., Sordo, J. & Touceda, Á. (2007). Coord. Chem. Rev. 251, 1561–1589. Web of Science CrossRef CAS Google Scholar
Jensen, B. S. (1959). Acta Chem. Scand. 13, 1668–1670. CrossRef CAS Web of Science Google Scholar
Li, J.-Z., Li, G. & Yu, W.-J. (2000). J. Rare Earth, 18, 233–236. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS 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

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Volume 67| Part 8| August 2011| Page o1936

doi:10.1107/S1600536811026158

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

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

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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