Crystal structure of 3-{1-[(1-allyl-1H-indazol-6-yl)amino]­ethyl­idene}-6-methyl-2H-pyran-2,4(3H)-dione

El Ghozlani, M.; Rakib, E.M.; Gamouh, A.; Saadi, M.; El Ammari, L.

doi:10.1107/S1600536814024520

organic compounds

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ISSN: 2056-9890

Volume 70| Part 12| December 2014| Page o1256

doi:10.1107/S1600536814024520

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Crystal structure of 3-{1-[(1-allyl-1H-indazol-6-yl)amino]ethylidene}-6-methyl-2H-pyran-2,4(3H)-dione

Mohamed El Ghozlani,^a ^* El Mostapha Rakib,^a Ahmed Gamouh,^a Mohamed Saadi ^b and Lahcen El Ammari ^b

^aLaboratoire de Chimie Organique et Analytique, Université Sultan Moulay Slimane, Faculté des Sciences et Techniques, Béni-Mellal, BP 523, Morocco, and ^bLaboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Université Mohammed V-Agdal, Avenue Ibn Battouta, BP 1014, Rabat, Morocco
^*Correspondence e-mail: m_elghozlani@yahoo.fr

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 6 November 2014; accepted 7 November 2014; online 15 November 2014)

In the title compound, C₁₈H₁₇N₃O₃, the dihedral angle between the planes of the indazole ring system [maximum deviation = 0.012 (1) Å] and the pyran-2,4-dione ring is 54.03 (6)°. An intramolecular N—H⋯O hydrogen bond closes an S(6) ring. The same H atom also participates in an intermolecular N—H⋯O hydrogen bond, which generates an inversion dimer. The dimers are linked by weak C—H⋯O contacts, thereby forming a three-dimensional network.

Keywords: crystal structure; pyran-2,4-dione; pharmacological activity; indazole derivatives.

CCDC reference: 1033266

1. Related literature

For pharmacological activities of indazole derivatives, see: Cerecetto et al. (2005 ); Jennings & Tennant (2007 ); Sun et al. (1997 ). For innovative methods in their synthesis, see: Paul et al. (2014 ).

2. Experimental

2.1. Crystal data

C₁₈H₁₇N₃O₃
M_r = 323.35
Triclinic, $[P \overline 1]$
a = 6.7708 (11) Å
b = 10.5761 (17) Å
c = 11.9643 (17) Å
α = 88.239 (9)°
β = 81.123 (9)°
γ = 79.140 (9)°
V = 831.3 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.39 × 0.34 × 0.29 mm

2.2. Data collection

Bruker X8 APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.685, T_max = 0.746
11752 measured reflections
3929 independent reflections
2930 reflections with I > 2σ(I)
R_int = 0.027

2.3. Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.131
S = 1.04
3929 reflections
217 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3N⋯O3	0.91	1.77	2.5567 (15)	143
N3—H3N⋯O3ⁱ	0.91	2.51	3.0612 (16)	120
C6—H6⋯O1ⁱⁱ	0.93	2.54	3.3554 (19)	146
C8—H8A⋯O1ⁱⁱ	0.97	2.53	3.495 (2)	173
Symmetry codes: (i) -x+1, -y, -z+1; (ii) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); 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 for Windows (Farrugia, 2012 ); software used to prepare material for publication: PLATON (Spek, 2009 ) and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 1033266

Crystal structure: contains datablock I. DOI: 10.1107/S1600536814024520/hb7311sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814024520/hb7311Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814024520/hb7311Isup3.cml

checkCIF report

Comment top

Pharmacologically active indazole and its derivatives are widely used as drug in treating various human diseases including cancer, inflammation, cardiovascular, and others (Cerecetto, et al., 2005; Jennings & Tennant, 2007; Sun, et al., 1997). This has incited researchers to develop innovative methods in their synthesis (Paul, et al., 2014).

The two fused five- and six-membered rings (N1/N2/C1 to C7), part of the molecule of the title compound, are almost planar, with the maximum deviation of 0.012 (1) Å arising from atom N1. The fused rings system is nearly perpendicular to the allyl group (C8 C9 C10) as shown in Fig. 1 (torsion angle C9 C8 N1 C7 = 88.9 (2)°). Moreover, the dihedral angle between the indazole system and the plan through the atoms forming the pyran-2 ring (C12 to C16O) is 54.03 (6)°.

In the crystal, molecules are connected through N—H···O hydrogen bonds in the way to build dimers which are linked by weak C—H···O contacts, forming a three-dimensional network as shown in Fig.2 and Table 2.

Related literature top

For pharmacological activities of indazole derivatives, see: Cerecetto et al. (2005); Jennings & Tennant (2007); Sun et al. (1997). For innovative methods in their synthesis, see: Paul et al. (2014).

Experimental top

1-Allyl-6-nitroindazole (1.0 mmol) was added to a mixture of indium powder (450 mg, 3.91 mmol), and acetic acid (1.12 ml, 10 mmol) in THF (2 ml), followed by the addition of 4-hydroxy-6-methyl-2-pyrone (1.0 mmol) in THF (3 ml). The reaction mixture was stirred at 353 K. After the reaction was completed, the reaction mixture was diluted with ethyl acetate (30 ml), filtered through Celite, poured into 10% K₂CO₃ (25 ml), and then extracted with ethyl acetate (30 ml x 3). The combined organic extracts were dried over MgSO₄, filtered, and concentrated. The resulting residue was purified by flash chromatography (eluted with Ethyl acetate: Hexane 4:6). The title compound was recrystallized from the solvent mixture ethyl acetate/hexane to yield yellow blocks (yield: 85%, m.p.: 392 K).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Figures top

Figure 1 Molecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level.

Figure 2 Partial crystal packing for the title compound showing N3—H3N···O3, C6—H6···O1 and C8—H8A···O1 hydrogen bonds as dashed lines.

3-{1-[(1-Allyl-1H-indazol-6-yl)amino]ethylidene}-6-methyl-2H-pyran-2,4(3H)-dione top

Crystal data top

C₁₈H₁₇N₃O₃	Z = 2
M_r = 323.35	F(000) = 340
Triclinic, P1	D_x = 1.292 Mg m⁻³
Hall symbol: -P 1	Melting point: 392 K
a = 6.7708 (11) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.5761 (17) Å	Cell parameters from 3929 reflections
c = 11.9643 (17) Å	θ = 2.6–27.9°
α = 88.239 (9)°	µ = 0.09 mm⁻¹
β = 81.123 (9)°	T = 296 K
γ = 79.140 (9)°	Block, yellow
V = 831.3 (2) Å³	0.39 × 0.34 × 0.29 mm

Data collection top

Bruker X8 APEX CCD diffractometer	3929 independent reflections
Radiation source: fine-focus sealed tube	2930 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ϕ and ω scans	θ_max = 27.9°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −8→8
T_min = 0.685, T_max = 0.746	k = −12→13
11752 measured reflections	l = −15→15

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.131	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0634P)² + 0.1441P] where P = (F_o² + 2F_c²)/3
3929 reflections	(Δ/σ)_max < 0.001
217 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₁₈H₁₇N₃O₃	γ = 79.140 (9)°
M_r = 323.35	V = 831.3 (2) Å³
Triclinic, P1	Z = 2
a = 6.7708 (11) Å	Mo Kα radiation
b = 10.5761 (17) Å	µ = 0.09 mm⁻¹
c = 11.9643 (17) Å	T = 296 K
α = 88.239 (9)°	0.39 × 0.34 × 0.29 mm
β = 81.123 (9)°

Data collection top

Bruker X8 APEX CCD diffractometer	3929 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2930 reflections with I > 2σ(I)
T_min = 0.685, T_max = 0.746	R_int = 0.027
11752 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.131	H-atom parameters constrained
S = 1.04	Δρ_max = 0.19 e Å⁻³
3929 reflections	Δρ_min = −0.19 e Å⁻³
217 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	−0.2126 (2)	0.27561 (17)	0.19077 (14)	0.0535 (4)
H1	−0.3315	0.2495	0.1792	0.064*
C2	−0.1187 (2)	0.24555 (13)	0.28909 (11)	0.0394 (3)
C3	−0.1571 (2)	0.17674 (15)	0.38933 (12)	0.0453 (4)
H3	−0.2704	0.1375	0.4040	0.054*
C4	−0.0230 (2)	0.16880 (14)	0.46546 (11)	0.0419 (3)
H4	−0.0454	0.1230	0.5324	0.050*
C5	0.14799 (19)	0.22876 (12)	0.44391 (10)	0.0327 (3)
C6	0.1916 (2)	0.29707 (12)	0.34631 (10)	0.0347 (3)
H6	0.3054	0.3358	0.3323	0.042*
C7	0.0533 (2)	0.30446 (12)	0.26930 (10)	0.0352 (3)
C8	0.2094 (3)	0.42381 (18)	0.10121 (14)	0.0664 (5)
H8A	0.2818	0.4594	0.1529	0.080*
H8B	0.1464	0.4943	0.0572	0.080*
C9	0.3587 (4)	0.3318 (3)	0.02309 (16)	0.0820 (7)
H9	0.4607	0.3652	−0.0227	0.098*
C10	0.3598 (3)	0.2112 (3)	0.01307 (18)	0.0866 (7)
H10A	0.2609	0.1733	0.0570	0.104*
H10B	0.4595	0.1616	−0.0382	0.104*
C11	0.3460 (2)	0.29146 (12)	0.58397 (10)	0.0349 (3)
C12	0.4993 (2)	0.24657 (12)	0.65330 (10)	0.0341 (3)
C13	0.5675 (2)	0.11088 (13)	0.66967 (10)	0.0359 (3)
C14	0.7230 (2)	0.07406 (14)	0.74087 (11)	0.0429 (3)
H14	0.7646	−0.0126	0.7568	0.051*
C15	0.8078 (2)	0.16072 (16)	0.78399 (12)	0.0474 (4)
C16	0.5936 (3)	0.33761 (15)	0.70210 (12)	0.0482 (4)
C17	0.2422 (3)	0.42837 (15)	0.57937 (16)	0.0671 (6)
H17A	0.1140	0.4326	0.5532	0.101*
H17B	0.3260	0.4753	0.5284	0.101*
H17C	0.2197	0.4655	0.6535	0.101*
C18	0.9761 (3)	0.1362 (2)	0.85373 (18)	0.0806 (6)
H18A	0.9316	0.1796	0.9250	0.121*
H18C	1.0918	0.1679	0.8145	0.121*
H18B	1.0133	0.0454	0.8665	0.121*
N1	0.0511 (2)	0.36448 (12)	0.16653 (10)	0.0472 (3)
N2	−0.1112 (2)	0.34456 (14)	0.11844 (11)	0.0574 (4)
N3	0.28794 (17)	0.20639 (10)	0.52426 (9)	0.0350 (3)
H3N	0.3443	0.1235	0.5379	0.042*
O1	0.5633 (3)	0.45366 (11)	0.69316 (13)	0.0832 (5)
O2	0.74794 (18)	0.28942 (11)	0.76619 (9)	0.0567 (3)
O3	0.50060 (18)	0.02513 (9)	0.62444 (9)	0.0538 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0429 (9)	0.0691 (11)	0.0520 (9)	−0.0058 (8)	−0.0233 (7)	−0.0044 (8)
C2	0.0330 (7)	0.0437 (8)	0.0413 (7)	−0.0003 (6)	−0.0124 (5)	−0.0057 (6)
C3	0.0325 (7)	0.0595 (9)	0.0459 (8)	−0.0136 (6)	−0.0057 (6)	−0.0009 (7)
C4	0.0404 (8)	0.0494 (8)	0.0360 (7)	−0.0096 (6)	−0.0055 (6)	0.0045 (6)
C5	0.0351 (7)	0.0320 (6)	0.0313 (6)	−0.0016 (5)	−0.0108 (5)	−0.0025 (5)
C6	0.0392 (7)	0.0317 (6)	0.0362 (6)	−0.0083 (5)	−0.0128 (5)	0.0005 (5)
C7	0.0413 (7)	0.0306 (6)	0.0340 (6)	−0.0015 (5)	−0.0130 (5)	−0.0012 (5)
C8	0.1033 (15)	0.0663 (11)	0.0490 (9)	−0.0470 (11)	−0.0384 (10)	0.0265 (8)
C9	0.0885 (15)	0.130 (2)	0.0434 (9)	−0.0647 (15)	−0.0069 (10)	0.0047 (11)
C10	0.0708 (14)	0.125 (2)	0.0651 (12)	−0.0253 (14)	0.0001 (10)	−0.0205 (13)
C11	0.0409 (7)	0.0328 (7)	0.0307 (6)	−0.0022 (5)	−0.0090 (5)	−0.0023 (5)
C12	0.0401 (7)	0.0347 (7)	0.0288 (6)	−0.0061 (5)	−0.0099 (5)	−0.0020 (5)
C13	0.0405 (7)	0.0375 (7)	0.0298 (6)	−0.0037 (6)	−0.0102 (5)	−0.0011 (5)
C14	0.0483 (8)	0.0446 (8)	0.0344 (6)	0.0024 (6)	−0.0160 (6)	0.0005 (6)
C15	0.0472 (9)	0.0594 (9)	0.0366 (7)	−0.0040 (7)	−0.0163 (6)	−0.0006 (6)
C16	0.0641 (10)	0.0441 (8)	0.0438 (8)	−0.0155 (7)	−0.0247 (7)	0.0010 (6)
C17	0.0909 (14)	0.0388 (8)	0.0736 (11)	0.0151 (8)	−0.0484 (10)	−0.0163 (8)
C18	0.0723 (13)	0.1046 (16)	0.0736 (12)	−0.0078 (12)	−0.0479 (11)	−0.0039 (11)
N1	0.0629 (8)	0.0466 (7)	0.0385 (6)	−0.0134 (6)	−0.0258 (6)	0.0080 (5)
N2	0.0622 (9)	0.0659 (9)	0.0493 (7)	−0.0067 (7)	−0.0324 (7)	0.0040 (6)
N3	0.0408 (6)	0.0308 (5)	0.0347 (5)	−0.0014 (5)	−0.0159 (5)	0.0006 (4)
O1	0.1312 (13)	0.0405 (7)	0.1001 (10)	−0.0286 (7)	−0.0724 (10)	0.0073 (6)
O2	0.0669 (7)	0.0579 (7)	0.0567 (6)	−0.0191 (6)	−0.0349 (6)	−0.0013 (5)
O3	0.0747 (8)	0.0333 (5)	0.0610 (7)	−0.0055 (5)	−0.0394 (6)	−0.0006 (4)

Geometric parameters (Å, º) top

C1—N2	1.311 (2)	C11—N3	1.3166 (16)
C1—C2	1.4215 (19)	C11—C12	1.4309 (18)
C1—H1	0.9300	C11—C17	1.4890 (19)
C2—C3	1.399 (2)	C12—C16	1.4339 (18)
C2—C7	1.407 (2)	C12—C13	1.4394 (18)
C3—C4	1.3723 (19)	C13—O3	1.2575 (16)
C3—H3	0.9300	C13—C14	1.4447 (18)
C4—C5	1.408 (2)	C14—C15	1.325 (2)
C4—H4	0.9300	C14—H14	0.9300
C5—C6	1.3765 (18)	C15—O2	1.3649 (19)
C5—N3	1.4355 (15)	C15—C18	1.494 (2)
C6—C7	1.4022 (17)	C16—O1	1.2099 (19)
C6—H6	0.9300	C16—O2	1.4010 (18)
C7—N1	1.3672 (17)	C17—H17A	0.9600
C8—N1	1.456 (2)	C17—H17B	0.9600
C8—C9	1.495 (3)	C17—H17C	0.9600
C8—H8A	0.9700	C18—H18A	0.9600
C8—H8B	0.9700	C18—H18C	0.9600
C9—C10	1.284 (3)	C18—H18B	0.9600
C9—H9	0.9300	N1—N2	1.3684 (18)
C10—H10A	0.9300	N3—H3N	0.9090
C10—H10B	0.9300

N2—C1—C2	111.83 (14)	C11—C12—C16	119.56 (12)
N2—C1—H1	124.1	C11—C12—C13	120.72 (11)
C2—C1—H1	124.1	C16—C12—C13	119.64 (12)
C3—C2—C7	119.78 (12)	O3—C13—C12	123.39 (12)
C3—C2—C1	136.29 (14)	O3—C13—C14	119.55 (12)
C7—C2—C1	103.93 (13)	C12—C13—C14	117.06 (12)
C4—C3—C2	118.11 (13)	C15—C14—C13	121.62 (13)
C4—C3—H3	120.9	C15—C14—H14	119.2
C2—C3—H3	120.9	C13—C14—H14	119.2
C3—C4—C5	121.11 (13)	C14—C15—O2	121.58 (13)
C3—C4—H4	119.4	C14—C15—C18	127.34 (16)
C5—C4—H4	119.4	O2—C15—C18	111.07 (14)
C6—C5—C4	122.61 (12)	O1—C16—O2	113.34 (13)
C6—C5—N3	120.24 (12)	O1—C16—C12	128.87 (14)
C4—C5—N3	116.93 (11)	O2—C16—C12	117.75 (13)
C5—C6—C7	115.68 (12)	C11—C17—H17A	109.5
C5—C6—H6	122.2	C11—C17—H17B	109.5
C7—C6—H6	122.2	H17A—C17—H17B	109.5
N1—C7—C6	130.43 (13)	C11—C17—H17C	109.5
N1—C7—C2	106.87 (12)	H17A—C17—H17C	109.5
C6—C7—C2	122.70 (12)	H17B—C17—H17C	109.5
N1—C8—C9	113.14 (15)	C15—C18—H18A	109.5
N1—C8—H8A	109.0	C15—C18—H18C	109.5
C9—C8—H8A	109.0	H18A—C18—H18C	109.5
N1—C8—H8B	109.0	C15—C18—H18B	109.5
C9—C8—H8B	109.0	H18A—C18—H18B	109.5
H8A—C8—H8B	107.8	H18C—C18—H18B	109.5
C10—C9—C8	126.33 (19)	C7—N1—N2	110.85 (13)
C10—C9—H9	116.8	C7—N1—C8	128.13 (13)
C8—C9—H9	116.8	N2—N1—C8	120.20 (12)
C9—C10—H10A	120.0	C1—N2—N1	106.50 (12)
C9—C10—H10B	120.0	C11—N3—C5	128.38 (11)
H10A—C10—H10B	120.0	C11—N3—H3N	113.9
N3—C11—C12	118.25 (11)	C5—N3—H3N	117.7
N3—C11—C17	118.15 (12)	C15—O2—C16	122.25 (11)
C12—C11—C17	123.55 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N···O3	0.91	1.77	2.5567 (15)	143
N3—H3N···O3ⁱ	0.91	2.51	3.0612 (16)	120
C6—H6···O1ⁱⁱ	0.93	2.54	3.3554 (19)	146
C8—H8A···O1ⁱⁱ	0.97	2.53	3.495 (2)	173

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N···O3	0.91	1.77	2.5567 (15)	143
N3—H3N···O3ⁱ	0.91	2.51	3.0612 (16)	120
C6—H6···O1ⁱⁱ	0.93	2.54	3.3554 (19)	146
C8—H8A···O1ⁱⁱ	0.97	2.53	3.495 (2)	173

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

Acknowledgements

The authors thank the Unit of Support for Technical and Scientific Research (UATRS, CNRST) for the X-ray measurements and the University Sultan Moulay Slimane, Beni-Mellal, Morocco, for financial support.

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

Crystal structure of 3-{1-[(1-allyl-1H-indazol-6-yl)amino]­ethyl­­idene}-6-methyl-2H-pyran-2,4(3H)-dione

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 3-{1-[(1-allyl-1H-indazol-6-yl)amino]ethylidene}-6-methyl-2H-pyran-2,4(3H)-dione