Crystal structure of (4Z)-4-[(di­methyl­amino)­methyl­idene]-3,5-dioxo-2-phenyl­pyrazolidine-1-carbaldehyde

Mague, J.T.; Mohamed, S.K.; Akkurt, M.; Ahmed, E.A.; Khodairy, A.

doi:10.1107/S2056989015010038

organic compounds

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ISSN: 2056-9890

Volume 71| Part 7| July 2015| Pages o440-o441

doi:10.1107/S2056989015010038

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Crystal structure of (4Z)-4-[(dimethylamino)methylidene]-3,5-dioxo-2-phenylpyrazolidine-1-carbaldehyde

Joel T. Mague,^a Shaaban K. Mohamed,^b,^c Mehmet Akkurt,^d Eman A. Ahmed ^e ^* and Ahmed Khodairy ^e

^aDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA, ^bChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, ^cChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt, ^dDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, and ^eChemistry Department, Faculty of Science, Sohag University, 82524 Sohag, Egypt
^*Correspondence e-mail: abdala_15@yahoo.com

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 12 May 2015; accepted 23 May 2015; online 3 June 2015)

In the title compound, C₁₃H₁₃N₃O₃, the pyrazolidine ring adopts a shallow envelope conformation, with the carbonyl C atom closest to the benzene ring as the flap [deviation of 0.126 (1) Å from the plane through the remaining atoms (r.m.s. deviation = 0.011 Å)]. The dihedral angle between the pyrazolidine ring (all atoms) and the benzene ring is 51.09 (4)°. An extremely short (2.08 Å) intramolecular C—H⋯O contact is seen. In the crystal, molecules are linked by C—H⋯O bonds, generating [010] chains. Extremely weak C—H⋯π interactions are also observed.

Keywords: crystal structure; pyrazolones; short intramolecular C—H⋯O contact; C—H⋯O hydrogen bonds; C—H⋯π interactions.

CCDC reference: 1402532

1. Related literature

For biological studies of azole compounds, see: Patel et al. (2012 ); Vijesh et al. (2011 ). For various medicinal and industrial applications of pyrrazole-containing compounds, see: Jin et al. (2011 ); Zhang et al. (2010 ); El-Sabbagh et al. (2009 ); Dekhane et al. (2011 ); Rostom et al. (2003 ); Zhou et al. (2010 ); Finkelstein & Strock (1997 ).

2. Experimental

2.1. Crystal data

C₁₃H₁₃N₃O₃
M_r = 259.26
Monoclinic, C 2/c
a = 26.4235 (9) Å
b = 6.1033 (2) Å
c = 16.8611 (6) Å
β = 113.272 (1)°
V = 2497.96 (15) Å³
Z = 8
Cu Kα radiation
μ = 0.84 mm⁻¹
T = 150 K
0.24 × 0.15 × 0.05 mm

2.2. Data collection

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer
Absorption correction: multi-scan (TWINABS; Sheldrick, 2009 ) T_min = 0.82, T_max = 0.96
26486 measured reflections
4565 independent reflections
3979 reflections with I > 2σ(I)
R_int = 0.021

2.3. Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.104
S = 1.04
4565 reflections
175 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1/C2/C3/N1/N2 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6A⋯O2	0.98	2.08	3.016 (2)	160
C5—H5C⋯O3ⁱ	0.98	2.52	3.1803 (19)	124
C7—H7⋯O2ⁱⁱ	0.95	2.29	3.0663 (16)	139
C5—H5B⋯Cg1ⁱⁱⁱ	0.98	2.98	3.8823 (18)	153
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+1, -y, -z+1; (iii) $[-x+1, y, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2014 ); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT; program(s) used to solve structure: SHELXT (Sheldrick, 2015a ); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b ); molecular graphics: DIAMOND (Brandenburg & Putz, 2012 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ).

Supporting information

CCDC reference: 1402532

Crystal structure: contains datablocks global, I. DOI: 10.1107/S2056989015010038/hb7425sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989015010038/hb7425Isup2.hkl

Supporting information file. DOI: 10.1107/S2056989015010038/hb7425Isup3.cml

checkCIF report

Comment top

Azole compounds are extensively studied and widely used as anti-microbial agents (Patel et al., 2012; Vijesh et al., 2011). Recently, urea derivatives of pyrazole have been reported as potent inhibitors of p38 kinase (Jin et al., 2011). Many of other pyrazole scaffold compounds are reported to have broad spectra of biological activities, such as anti-fungal (Zhang et al., 2010), anti-viral (El-Sabbagh et al., 2009), anti-inflammatory (Dekhane et al., 2011), anti-tumor, anti-HCV (Rostom et al., 2003), herbicidal (Zhou et al., 2010) and insecticidal activities (Finkelstein & Strock, 1997). In view of such findings and as a continuation of our study on the synthesis of potential bio-active heterocyclic molecules, we report here the synthesis and crystal structure of the title compound.

In the title compound, the pyrazolidine ring is slightly twisted with an r.m.s. deviation from the mean plane of the 5 atoms forming the ring of 0.036 Å. The dihedral angle between this plane and that of the phenyl ring is 51.09 (4)° (Fig. 1).

Related literature top

For biological studies of azole compounds, see: Patel et al. (2012); Vijesh et al. (2011). For various medicinal and industrial applications of pyrrazole-containing compounds, see: Jin et al. (2011); Zhang et al. (2010); El-Sabbagh et al. (2009); Dekhane et al. (2011); Rostom et al. (2003); Zhou et al. (2010); Finkelstein & Strock (1997).

Experimental top

To phosphorous oxychloride (0.1 mol, 10 ml), in a conical flask with a magnetic stirrer, dry dimethylformamide (35 ml) was added drop-wise with stirring at 303–308 K for 30 min. Then a solution of 1-phenylpyrazolidine-3,5-dione (0.05 mol, 8.8 g) in dimethylformamide (15 ml), was added drop-wise with continuous stirring while ensuring that the temperature did not exceed 318 K. The reaction mixture was stirred overnight and poured onto crushed ice. The solid product was collected by filtration and recrystallized from ethanol to give colourless crystals in 75% yield (m. p. 453–455 K).

Computing details top

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The title molecule with 50% probability ellipsoids.
	Fig. 2. Packing viewed down the b axis. C—H···π interactions are shown by dotted lines.

(4Z)-4-[(Dimethylamino)methylidene]-3,5-dioxo-2-phenylpyrazolidine-1-carbaldehyde top

Crystal data top

C₁₃H₁₃N₃O₃	F(000) = 1088
M_r = 259.26	D_x = 1.379 Mg m⁻³
Monoclinic, C2/c	Cu Kα radiation, λ = 1.54178 Å
a = 26.4235 (9) Å	Cell parameters from 9978 reflections
b = 6.1033 (2) Å	θ = 3.6–72.3°
c = 16.8611 (6) Å	µ = 0.84 mm⁻¹
β = 113.272 (1)°	T = 150 K
V = 2497.96 (15) Å³	Rod, colourless
Z = 8	0.24 × 0.15 × 0.05 mm

Data collection top

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	4565 independent reflections
Radiation source: INCOATEC IµS micro–focus source	3979 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.021
Detector resolution: 10.4167 pixels mm^-1	θ_max = 72.3°, θ_min = 3.6°
ω scans	h = −32→30
Absorption correction: multi-scan (TWINABS; Sheldrick, 2009)	k = −7→7
T_min = 0.82, T_max = 0.96	l = −20→20
26486 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: inferred from neighbouring sites
wR(F²) = 0.104	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0577P)² + 0.7347P] where P = (F_o² + 2F_c²)/3
4565 reflections	(Δ/σ)_max < 0.001
175 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₃H₁₃N₃O₃	V = 2497.96 (15) Å³
M_r = 259.26	Z = 8
Monoclinic, C2/c	Cu Kα radiation
a = 26.4235 (9) Å	µ = 0.84 mm⁻¹
b = 6.1033 (2) Å	T = 150 K
c = 16.8611 (6) Å	0.24 × 0.15 × 0.05 mm
β = 113.272 (1)°

Data collection top

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	4565 independent reflections
Absorption correction: multi-scan (TWINABS; Sheldrick, 2009)	3979 reflections with I > 2σ(I)
T_min = 0.82, T_max = 0.96	R_int = 0.021
26486 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.104	H-atom parameters constrained
S = 1.04	Δρ_max = 0.26 e Å⁻³
4565 reflections	Δρ_min = −0.20 e Å⁻³
175 parameters

Special details top

Experimental. Analysis of 3764 reflections having I/σ(I) > 12 and chosen from

the full data set with CELL_NOW (Sheldrick, 2008) showed

the crystal to belong to the monoclinic system and to be twinned

by a 180° rotation about the c* axis. The raw data were

processed using the multi-component version of SAINT under

control of the two-component orientation file generated by

CELL_NOW.

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. H-atoms were placed in

calculated positions (C—H = 0.95 - 0.98 Å) and included as riding

contributions with isotropic displacement parameters 1.2 - 1.5 times those

of the attached carbon atoms. The model was refined as a 2-component twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.43175 (4)	0.79022 (16)	0.28697 (7)	0.0296 (2)
O2	0.52891 (4)	0.15926 (16)	0.42906 (7)	0.0324 (3)
O3	0.37052 (4)	0.10698 (18)	0.39957 (6)	0.0316 (3)
N1	0.40831 (4)	0.46179 (18)	0.33205 (7)	0.0236 (3)
N2	0.43832 (4)	0.26978 (18)	0.36829 (7)	0.0239 (3)
N3	0.59876 (5)	0.64368 (19)	0.42207 (8)	0.0265 (3)
C1	0.44610 (5)	0.6170 (2)	0.32599 (8)	0.0233 (3)
C2	0.50109 (5)	0.5284 (2)	0.37179 (8)	0.0235 (3)
C3	0.49589 (5)	0.3060 (2)	0.39467 (8)	0.0242 (3)
C4	0.54556 (5)	0.6654 (2)	0.38045 (9)	0.0249 (3)
H4	0.5349	0.8001	0.3502	0.030*
C5	0.63539 (6)	0.8195 (3)	0.41755 (10)	0.0344 (3)
H5A	0.6133	0.9445	0.3861	0.052*
H5B	0.6580	0.7661	0.3874	0.052*
H5C	0.6594	0.8652	0.4761	0.052*
C6	0.62712 (6)	0.4598 (3)	0.47712 (10)	0.0344 (3)
H6A	0.6002	0.3471	0.4750	0.052*
H6B	0.6462	0.5109	0.5367	0.052*
H6C	0.6540	0.3978	0.4566	0.052*
C7	0.41757 (5)	0.1104 (2)	0.40511 (8)	0.0255 (3)
H7	0.4416	−0.0034	0.4367	0.031*
C8	0.35475 (5)	0.4373 (2)	0.26388 (8)	0.0235 (3)
C9	0.34078 (5)	0.2502 (2)	0.21315 (9)	0.0275 (3)
H9	0.3667	0.1349	0.2227	0.033*
C10	0.28831 (6)	0.2336 (3)	0.14813 (9)	0.0311 (3)
H10	0.2783	0.1062	0.1129	0.037*
C11	0.25040 (6)	0.4019 (3)	0.13433 (9)	0.0311 (3)
H11	0.2146	0.3899	0.0897	0.037*
C12	0.26490 (6)	0.5880 (2)	0.18593 (10)	0.0308 (3)
H12	0.2390	0.7031	0.1765	0.037*
C13	0.31717 (5)	0.6066 (2)	0.25127 (9)	0.0271 (3)
H13	0.3271	0.7333	0.2868	0.033*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0274 (5)	0.0239 (5)	0.0339 (5)	0.0033 (4)	0.0083 (4)	0.0053 (4)
O2	0.0221 (5)	0.0284 (5)	0.0409 (6)	0.0034 (4)	0.0063 (4)	0.0100 (4)
O3	0.0259 (5)	0.0404 (6)	0.0290 (5)	−0.0054 (4)	0.0115 (4)	0.0019 (4)
N1	0.0201 (5)	0.0227 (6)	0.0262 (6)	0.0027 (4)	0.0072 (4)	0.0031 (4)
N2	0.0190 (5)	0.0234 (6)	0.0267 (6)	0.0013 (4)	0.0062 (4)	0.0053 (4)
N3	0.0232 (5)	0.0306 (6)	0.0260 (6)	−0.0047 (4)	0.0099 (4)	−0.0026 (5)
C1	0.0241 (6)	0.0232 (6)	0.0227 (6)	0.0005 (5)	0.0093 (5)	−0.0009 (5)
C2	0.0211 (6)	0.0252 (7)	0.0233 (6)	0.0009 (5)	0.0077 (5)	0.0017 (5)
C3	0.0206 (6)	0.0268 (6)	0.0231 (6)	−0.0003 (5)	0.0063 (5)	0.0013 (5)
C4	0.0266 (6)	0.0250 (6)	0.0233 (6)	−0.0015 (5)	0.0102 (5)	−0.0005 (5)
C5	0.0296 (7)	0.0432 (8)	0.0314 (7)	−0.0132 (6)	0.0132 (6)	−0.0043 (7)
C6	0.0237 (6)	0.0348 (8)	0.0386 (8)	0.0007 (6)	0.0059 (6)	−0.0005 (6)
C7	0.0254 (6)	0.0271 (7)	0.0216 (6)	−0.0029 (5)	0.0066 (5)	0.0022 (5)
C8	0.0195 (6)	0.0289 (7)	0.0227 (6)	0.0010 (5)	0.0090 (5)	0.0033 (5)
C9	0.0247 (6)	0.0310 (7)	0.0258 (7)	0.0054 (5)	0.0089 (5)	0.0001 (5)
C10	0.0289 (7)	0.0344 (8)	0.0273 (7)	−0.0001 (6)	0.0082 (6)	−0.0029 (6)
C11	0.0212 (6)	0.0397 (8)	0.0281 (7)	0.0010 (6)	0.0053 (5)	0.0056 (6)
C12	0.0222 (6)	0.0319 (7)	0.0383 (8)	0.0060 (5)	0.0121 (6)	0.0072 (6)
C13	0.0240 (6)	0.0263 (7)	0.0326 (7)	0.0018 (5)	0.0128 (6)	0.0007 (5)

Geometric parameters (Å, º) top

O1—C1	1.2234 (17)	C5—H5C	0.9800
O2—C3	1.2247 (17)	C6—H6A	0.9800
O3—C7	1.2096 (17)	C6—H6B	0.9800
N1—C1	1.4094 (17)	C6—H6C	0.9800
N1—N2	1.4116 (15)	C7—H7	0.9500
N1—C8	1.4356 (16)	C8—C9	1.387 (2)
N2—C7	1.3789 (17)	C8—C13	1.3898 (18)
N2—C3	1.4236 (16)	C9—C10	1.3903 (19)
N3—C4	1.3064 (17)	C9—H9	0.9500
N3—C6	1.4607 (19)	C10—C11	1.389 (2)
N3—C5	1.4669 (18)	C10—H10	0.9500
C1—C2	1.4538 (17)	C11—C12	1.389 (2)
C2—C4	1.4019 (18)	C11—H11	0.9500
C2—C3	1.4324 (19)	C12—C13	1.390 (2)
C4—H4	0.9500	C12—H12	0.9500
C5—H5A	0.9800	C13—H13	0.9500
C5—H5B	0.9800

C1—N1—N2	107.25 (10)	N3—C6—H6A	109.5
C1—N1—C8	120.96 (11)	N3—C6—H6B	109.5
N2—N1—C8	117.89 (10)	H6A—C6—H6B	109.5
C7—N2—N1	121.70 (11)	N3—C6—H6C	109.5
C7—N2—C3	122.33 (11)	H6A—C6—H6C	109.5
N1—N2—C3	110.76 (10)	H6B—C6—H6C	109.5
C4—N3—C6	126.32 (12)	O3—C7—N2	123.82 (13)
C4—N3—C5	119.34 (12)	O3—C7—H7	118.1
C6—N3—C5	114.31 (12)	N2—C7—H7	118.1
O1—C1—N1	122.81 (12)	C9—C8—C13	121.19 (12)
O1—C1—C2	129.76 (12)	C9—C8—N1	121.16 (11)
N1—C1—C2	107.42 (11)	C13—C8—N1	117.64 (12)
C4—C2—C3	134.64 (12)	C8—C9—C10	119.07 (13)
C4—C2—C1	117.00 (12)	C8—C9—H9	120.5
C3—C2—C1	108.28 (11)	C10—C9—H9	120.5
O2—C3—N2	120.52 (12)	C11—C10—C9	120.43 (14)
O2—C3—C2	133.97 (12)	C11—C10—H10	119.8
N2—C3—C2	105.51 (11)	C9—C10—H10	119.8
N3—C4—C2	132.47 (13)	C10—C11—C12	119.85 (13)
N3—C4—H4	113.8	C10—C11—H11	120.1
C2—C4—H4	113.8	C12—C11—H11	120.1
N3—C5—H5A	109.5	C11—C12—C13	120.33 (13)
N3—C5—H5B	109.5	C11—C12—H12	119.8
H5A—C5—H5B	109.5	C13—C12—H12	119.8
N3—C5—H5C	109.5	C8—C13—C12	119.12 (13)
H5A—C5—H5C	109.5	C8—C13—H13	120.4
H5B—C5—H5C	109.5	C12—C13—H13	120.4

C1—N1—N2—C7	161.44 (12)	C1—C2—C3—N2	−4.26 (14)
C8—N1—N2—C7	−57.85 (16)	C6—N3—C4—C2	−2.8 (2)
C1—N1—N2—C3	6.44 (14)	C5—N3—C4—C2	179.28 (14)
C8—N1—N2—C3	147.14 (11)	C3—C2—C4—N3	−9.4 (3)
N2—N1—C1—O1	170.26 (12)	C1—C2—C4—N3	174.34 (14)
C8—N1—C1—O1	31.01 (19)	N1—N2—C7—O3	10.0 (2)
N2—N1—C1—C2	−8.87 (14)	C3—N2—C7—O3	162.12 (13)
C8—N1—C1—C2	−148.12 (11)	C1—N1—C8—C9	111.30 (15)
O1—C1—C2—C4	6.4 (2)	N2—N1—C8—C9	−23.84 (17)
N1—C1—C2—C4	−174.52 (11)	C1—N1—C8—C13	−69.53 (16)
O1—C1—C2—C3	−170.80 (13)	N2—N1—C8—C13	155.33 (12)
N1—C1—C2—C3	8.25 (14)	C13—C8—C9—C10	0.6 (2)
C7—N2—C3—O2	24.0 (2)	N1—C8—C9—C10	179.72 (13)
N1—N2—C3—O2	178.78 (12)	C8—C9—C10—C11	−0.2 (2)
C7—N2—C3—C2	−156.09 (12)	C9—C10—C11—C12	−0.2 (2)
N1—N2—C3—C2	−1.27 (14)	C10—C11—C12—C13	0.0 (2)
C4—C2—C3—O2	−0.8 (3)	C9—C8—C13—C12	−0.7 (2)
C1—C2—C3—O2	175.68 (15)	N1—C8—C13—C12	−179.87 (12)
C4—C2—C3—N2	179.21 (14)	C11—C12—C13—C8	0.4 (2)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1/C2/C3/N1/N2 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6A···O2	0.98	2.08	3.016 (2)	160
C5—H5C···O3ⁱ	0.98	2.52	3.1803 (19)	124
C7—H7···O2ⁱⁱ	0.95	2.29	3.0663 (16)	139
C5—H5B···Cg1ⁱⁱⁱ	0.98	2.98	3.8823 (18)	153

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

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1/C2/C3/N1/N2 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6A···O2	0.98	2.08	3.016 (2)	160
C5—H5C···O3ⁱ	0.98	2.52	3.1803 (19)	124
C7—H7···O2ⁱⁱ	0.95	2.29	3.0663 (16)	139
C5—H5B···Cg1ⁱⁱⁱ	0.98	2.98	3.8823 (18)	153

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

Acknowledgements

The support of NSF–MRI grant No. 1228232 for the purchase of the diffractometer and Tulane University for support of the Tulane Crystallography Laboratory are gratefully acknowledged.

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Volume 71| Part 7| July 2015| Pages o440-o441

doi:10.1107/S2056989015010038

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

Crystal structure of (4Z)-4-[(di­methyl­amino)­methyl­­idene]-3,5-dioxo-2-phenyl­pyrazolidine-1-carbaldehyde

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of (4Z)-4-[(dimethylamino)methylidene]-3,5-dioxo-2-phenylpyrazolidine-1-carbaldehyde