6-Amino-3-methyl-4-(3-nitro­phen­yl)-1-phenyl-1H,4H-pyrano[2,3-c]pyrazole-5-carbonitrile

Wu, M.-S.; Kong, D.-L.; Zhang, X.-Z.

doi:10.1107/S1600536811017387

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 6| June 2011| Pages o1454-o1455

doi:10.1107/S1600536811017387

Open

access

6-Amino-3-methyl-4-(3-nitrophenyl)-1-phenyl-1H,4H-pyrano[2,3-c]pyrazole-5-carbonitrile

Ming-Shu Wu,^a,^b ^* Du-Lin Kong ^b and Xiang-Zhu Zhang ^a

^aDepartment of Chemical Engineering, Anyang Institute of Technology, Anyang, Henan 455000, People's Republic of China, and ^bCollege of Chemistry & Chemical Engineering, Hainan Normal University, Haikou 571158, People's Republic of China
^*Correspondence e-mail: wumingshu@126.com

(Received 2 April 2011; accepted 9 May 2011; online 20 May 2011)

The title compound, C₂₀H₁₅N₅O₃, was synthesized by the one-pot reaction of a four-component reaction protocol in aqueous medium. The pyrano[2,3-c]pyrazole system is essentially planar, with a maximum deviation of 0.026 (2) Å. The 3-nitrophenyl and phenyl rings make dihedral angles of 81.11 (5) and 13.36 (1)°, respectively, with the mean plane of the pyrano[2,3-c]pyrazole ring. The crystal structure is stabilized by N—H⋯N hydrogen bonds, which form infinite chain propagating along the c axis and by N—H⋯O hydrogen bonds, which form infinite chains propagating along the a axis. There are also N—O⋯N—C dipole–dipole interactions along the a axis with an O⋯N distance of 3.061 (3) Å, which is shorter than that of the N—H⋯O hydrogen bond [3.196 (3) Å].

Related literature

For the antimicrobial, insecticidal and anti-inflammatory activity of pyranopyrazole derivatives, see: El-Tamany et al. (1999 ); Ismail et al. (2003 ); Zaki et al. (2006 ) and for their applications as pharmaceutical ingredients and biodegradable agrochemicals, see: Junek & Aigner (1973 ); Sharanin et al. (1983 ); Vasuki & Kumaravel (2008 ); Wamhoff et al. (1993 ). For the Chk1 kinase inhibitor, see: Foloppe et al. (2006 ). For the use of multi-component reaction (MCR) protocols in water in the development of libraries of medicinal scaffolds, see: Chanda & Fokin (2009 ); Tejedor & Garcia-Tellado (2007 ).

Experimental

Crystal data

C₂₀H₁₅N₅O₃
M_r = 373.37
Monoclinic, P 2₁ /c
a = 9.5089 (8) Å
b = 13.9137 (11) Å
c = 13.3747 (12) Å
β = 96.263 (1)°
V = 1759.0 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 298 K
0.50 × 0.48 × 0.47 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002 ) T_min = 0.952, T_max = 0.955
8659 measured reflections
3087 independent reflections
1961 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.121
S = 1.07
3087 reflections
255 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O2ⁱ	0.86	2.63	3.196 (3)	124
N3—H3B⋯N4ⁱⁱ	0.86	2.22	3.067 (3)	169
C19—H19⋯O2ⁱⁱⁱ	0.93	2.54	3.294 (4)	139
Symmetry codes: (i) x-1, y, z; (ii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); 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/S1600536811017387/zk2006sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811017387/zk2006Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811017387/zk2006Isup3.cml

checkCIF report

Comment top

Multi-component reaction (MCR) protocols in water will be one of the most suitable strategies, which will meet the requirements of green chemistry as well as for developing libraries of medicinal scaffolds (Chanda et al., 2009; Tejedor et al., 2007). pyranopyrazoles are an important class of heterocyclic compounds. They found applications as pharmaceutical ingredients and biodegradable agrochemicals (Junek et al., 1973; Wamhoff et al., 1993; Sharanin et al., 1983; Vasuki et al., 2008). In order to further study the structure-activity relationship of pyranopyrazoles, we performed the synthesis of the title compound through an efficient and eco-friendly four-component one-pot reaction protocol in aqueous medium in the presence of catalytic amount dodecyltrimethylammonium bromide and present the crystal structure of the title compound in the hope that its structural features will appear interesting and helpful its practical applications. In the title molecule (Fig. 1), The pyranopyrazole ring essentially planar with a maximum deviation of 0.026 (0) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angles formed by the mean plane of the pyranopyrazole fragment with the 3-nitrophenyl ring and phenyl ring is 81.11 (5)° and 13.36 (1)° , respectively. In the crystal the molecular packing (Fig. 2) is stabilized by Infinite chains via N-H···N hydrogen bonds propagate along c-axis, infinite chains via N-H···O hydrogen bonds propagate along a-axis and along a-axis there exists N-O···N-C dipole-dipole interactions with O···N distance of 3.061 Å which shorter than that of N-H···O (3.196 Å) hydrogen bond.

Related literature top

For the antimicrobial, insecticidal and anti-inflammatory activity of pyranopyrazole derivatives, see: El-Tamany et al. (1999); Ismail et al. (2003); Zaki et al. (2006) and for their applications as pharmaceutical ingredients and biodegradable agrochemicals, see: Junek & Aigner (1973); Sharanin et al. (1983); Vasuki & Kumaravel (2008); Wamhoff et al. (1993). For the Chk1 kinase inhibitor, see: Foloppe et al. (2006). For the use of multi-component reaction (MCR) protocols in water in the development of libraries of medicinal scaffolds, see: Chanda & Fokin (2009); Tejedor & Garcia-Tellado (2007).

Experimental top

To a stirred aqueous mixture of phenylhydrazine ( 0.216g, 2 mmol) and ethyl acetoacetate ( 0.260g, 2 mmol), 3-nitrobenzaldehyde ( 0.302g, 2 mmol), malonitrile ( 0.132g, 2 mmol) and piperidine (5 mol %) were added successively at 363 K in the presence of catalytic amount dodecyltrimethylammonium bromide with vigorous stirring for 10 min. The precipitated solid was filtered, washed with water and then with a mixture of ethyl acetate/hexane (20:80). The product obtained was purified by flash chromatograghy. Single crystals of the title compound suitable for single-crystal X-ray analysis were obtained by recrystallization from ethanol.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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 compound, with atom labels and 50% probability displacement ellipsoids for non-H atoms.
	Fig. 2. Crystal packing of the title compound, viewed along the a axis Intermolecular hydrogen bonds are shown as dashed lines.

6-Amino-3-methyl-4-(3-nitrophenyl)-1-phenyl-1H,4H- pyrano[2,3-c]pyrazole-5-carbonitrile top

Crystal data top

C₂₀H₁₅N₅O₃	F(000) = 776
M_r = 373.37	D_x = 1.410 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.5089 (8) Å	Cell parameters from 2416 reflections
b = 13.9137 (11) Å	θ = 2.6–23.5°
c = 13.3747 (12) Å	µ = 0.10 mm⁻¹
β = 96.263 (1)°	T = 298 K
V = 1759.0 (3) Å³	Plate, colourless
Z = 4	0.50 × 0.48 × 0.47 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3087 independent reflections
Radiation source: fine-focus sealed tube	1961 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.037
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −11→11
T_min = 0.952, T_max = 0.955	k = −16→16
8659 measured reflections	l = −9→15

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.042	H-atom parameters constrained
wR(F²) = 0.121	w = 1/[σ²(F_o²) + (0.0397P)² + 0.6842P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
3087 reflections	Δρ_max = 0.19 e Å⁻³
255 parameters	Δρ_min = −0.17 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0100 (13)

Crystal data top

C₂₀H₁₅N₅O₃	V = 1759.0 (3) Å³
M_r = 373.37	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.5089 (8) Å	µ = 0.10 mm⁻¹
b = 13.9137 (11) Å	T = 298 K
c = 13.3747 (12) Å	0.50 × 0.48 × 0.47 mm
β = 96.263 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3087 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2002)	1961 reflections with I > 2σ(I)
T_min = 0.952, T_max = 0.955	R_int = 0.037
8659 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.121	H-atom parameters constrained
S = 1.07	Δρ_max = 0.19 e Å⁻³
3087 reflections	Δρ_min = −0.17 e Å⁻³
255 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
N1	0.71933 (19)	0.52908 (13)	0.63123 (13)	0.0440 (5)
N2	0.8060 (2)	0.46605 (13)	0.58687 (15)	0.0507 (5)
N3	0.3851 (2)	0.75499 (15)	0.52319 (15)	0.0565 (6)
H3A	0.3339	0.7879	0.4785	0.068*
H3B	0.3776	0.7641	0.5860	0.068*
N4	0.3550 (2)	0.74422 (18)	0.24916 (17)	0.0741 (7)
N5	1.0378 (2)	0.80263 (17)	0.3702 (2)	0.0674 (7)
O1	0.54812 (16)	0.64832 (11)	0.57873 (10)	0.0471 (4)
O2	1.0555 (2)	0.79273 (15)	0.46155 (19)	0.0900 (7)
O3	1.1104 (2)	0.85581 (18)	0.3254 (2)	0.1121 (9)
C1	0.6433 (2)	0.57976 (15)	0.55812 (16)	0.0404 (5)
C2	0.6769 (2)	0.55266 (16)	0.46700 (16)	0.0418 (5)
C3	0.7801 (2)	0.48064 (16)	0.48860 (18)	0.0466 (6)
C4	0.8571 (3)	0.42635 (18)	0.4160 (2)	0.0625 (7)
H4A	0.9190	0.4691	0.3853	0.094*
H4B	0.7903	0.3987	0.3651	0.094*
H4C	0.9118	0.3761	0.4508	0.094*
C5	0.4761 (2)	0.68993 (16)	0.49508 (17)	0.0429 (6)
C6	0.5006 (2)	0.66700 (16)	0.40010 (16)	0.0429 (6)
C7	0.6133 (2)	0.59767 (16)	0.37153 (16)	0.0434 (6)
H7	0.5673	0.5474	0.3283	0.052*
C8	0.7221 (2)	0.64836 (16)	0.31459 (16)	0.0412 (5)
C9	0.8293 (2)	0.70132 (16)	0.36589 (17)	0.0445 (6)
H9	0.8368	0.7053	0.4357	0.053*
C10	0.9247 (2)	0.74805 (16)	0.31350 (19)	0.0482 (6)
C11	0.9187 (3)	0.74412 (19)	0.2108 (2)	0.0650 (7)
H11	0.9848	0.7762	0.1767	0.078*
C12	0.8126 (3)	0.6916 (2)	0.1602 (2)	0.0722 (8)
H12	0.8063	0.6875	0.0904	0.087*
C13	0.7148 (3)	0.64464 (19)	0.21116 (17)	0.0567 (7)
H13	0.6426	0.6098	0.1752	0.068*
C14	0.4173 (3)	0.71120 (18)	0.31880 (18)	0.0510 (6)
C15	0.7217 (3)	0.52889 (16)	0.73764 (17)	0.0466 (6)
C16	0.6181 (3)	0.57274 (18)	0.78491 (18)	0.0575 (7)
H16	0.5454	0.6060	0.7476	0.069*
C17	0.6223 (4)	0.5672 (2)	0.8885 (2)	0.0740 (9)
H17	0.5521	0.5967	0.9208	0.089*
C18	0.7290 (4)	0.5184 (2)	0.9436 (2)	0.0851 (10)
H18	0.7303	0.5137	1.0131	0.102*
C19	0.8331 (4)	0.4768 (2)	0.8965 (2)	0.0856 (10)
H19	0.9066	0.4449	0.9343	0.103*
C20	0.8312 (3)	0.4813 (2)	0.7935 (2)	0.0684 (8)
H20	0.9028	0.4527	0.7619	0.082*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0465 (11)	0.0447 (11)	0.0404 (11)	0.0003 (9)	0.0034 (9)	0.0016 (9)
N2	0.0507 (12)	0.0471 (12)	0.0553 (13)	0.0015 (10)	0.0105 (10)	0.0039 (10)
N3	0.0560 (12)	0.0692 (14)	0.0443 (12)	0.0159 (11)	0.0054 (10)	0.0013 (10)
N4	0.0683 (15)	0.1012 (19)	0.0511 (14)	0.0056 (14)	−0.0008 (12)	0.0171 (14)
N5	0.0482 (14)	0.0591 (14)	0.096 (2)	−0.0073 (11)	0.0149 (14)	−0.0085 (15)
O1	0.0511 (9)	0.0555 (10)	0.0340 (8)	0.0053 (8)	0.0018 (7)	−0.0017 (7)
O2	0.0833 (15)	0.0804 (14)	0.0994 (18)	−0.0252 (12)	−0.0219 (14)	−0.0020 (14)
O3	0.0880 (16)	0.1111 (18)	0.147 (2)	−0.0534 (15)	0.0570 (16)	−0.0233 (16)
C1	0.0384 (12)	0.0439 (13)	0.0394 (13)	−0.0043 (11)	0.0059 (10)	−0.0012 (11)
C2	0.0441 (13)	0.0418 (12)	0.0403 (13)	−0.0090 (10)	0.0079 (11)	0.0008 (10)
C3	0.0472 (14)	0.0436 (13)	0.0508 (15)	−0.0072 (11)	0.0140 (12)	0.0025 (11)
C4	0.0662 (17)	0.0579 (16)	0.0672 (17)	0.0054 (13)	0.0251 (14)	−0.0015 (14)
C5	0.0384 (12)	0.0509 (14)	0.0385 (13)	−0.0049 (11)	0.0008 (10)	0.0035 (11)
C6	0.0380 (12)	0.0541 (14)	0.0366 (13)	−0.0080 (11)	0.0035 (10)	0.0033 (11)
C7	0.0459 (13)	0.0486 (13)	0.0355 (13)	−0.0096 (11)	0.0043 (11)	−0.0063 (10)
C8	0.0429 (13)	0.0458 (13)	0.0351 (12)	0.0002 (10)	0.0056 (10)	−0.0018 (10)
C9	0.0458 (13)	0.0491 (13)	0.0390 (13)	0.0013 (11)	0.0061 (11)	−0.0019 (11)
C10	0.0412 (13)	0.0444 (13)	0.0606 (16)	−0.0014 (11)	0.0126 (12)	−0.0014 (12)
C11	0.0699 (18)	0.0646 (17)	0.0664 (18)	−0.0081 (15)	0.0342 (15)	0.0064 (15)
C12	0.089 (2)	0.090 (2)	0.0416 (15)	−0.0100 (18)	0.0238 (15)	0.0038 (15)
C13	0.0625 (16)	0.0697 (17)	0.0384 (14)	−0.0096 (14)	0.0074 (12)	−0.0054 (13)
C14	0.0469 (14)	0.0646 (16)	0.0416 (14)	−0.0040 (12)	0.0058 (12)	0.0037 (13)
C15	0.0578 (15)	0.0422 (13)	0.0382 (13)	−0.0122 (12)	−0.0012 (12)	0.0036 (11)
C16	0.0750 (18)	0.0536 (15)	0.0437 (15)	−0.0003 (13)	0.0049 (13)	−0.0018 (12)
C17	0.109 (2)	0.0685 (19)	0.0459 (16)	−0.0019 (17)	0.0144 (17)	−0.0063 (14)
C18	0.142 (3)	0.071 (2)	0.0397 (16)	−0.008 (2)	−0.005 (2)	0.0044 (15)
C19	0.113 (3)	0.081 (2)	0.056 (2)	0.008 (2)	−0.0179 (19)	0.0136 (17)
C20	0.0764 (19)	0.0700 (18)	0.0561 (17)	0.0042 (15)	−0.0050 (15)	0.0104 (14)

Geometric parameters (Å, º) top

N1—C1	1.350 (3)	C7—C8	1.523 (3)
N1—N2	1.381 (2)	C7—H7	0.9800
N1—C15	1.421 (3)	C8—C9	1.378 (3)
N2—C3	1.326 (3)	C8—C13	1.379 (3)
N3—C5	1.334 (3)	C9—C10	1.369 (3)
N3—H3A	0.8600	C9—H9	0.9300
N3—H3B	0.8600	C10—C11	1.370 (3)
N4—C14	1.144 (3)	C11—C12	1.364 (4)
N5—O3	1.214 (3)	C11—H11	0.9300
N5—O2	1.222 (3)	C12—C13	1.377 (4)
N5—C10	1.460 (3)	C12—H12	0.9300
O1—C1	1.364 (3)	C13—H13	0.9300
O1—C5	1.374 (2)	C15—C16	1.371 (3)
C1—C2	1.347 (3)	C15—C20	1.382 (3)
C2—C3	1.411 (3)	C16—C17	1.384 (3)
C2—C7	1.490 (3)	C16—H16	0.9300
C3—C4	1.484 (3)	C17—C18	1.367 (4)
C4—H4A	0.9600	C17—H17	0.9300
C4—H4B	0.9600	C18—C19	1.360 (4)
C4—H4C	0.9600	C18—H18	0.9300
C5—C6	1.354 (3)	C19—C20	1.377 (4)
C6—C14	1.414 (3)	C19—H19	0.9300
C6—C7	1.522 (3)	C20—H20	0.9300

C1—N1—N2	108.55 (17)	C9—C8—C13	118.2 (2)
C1—N1—C15	132.5 (2)	C9—C8—C7	120.29 (19)
N2—N1—C15	118.94 (18)	C13—C8—C7	121.5 (2)
C3—N2—N1	105.87 (18)	C10—C9—C8	119.6 (2)
C5—N3—H3A	120.0	C10—C9—H9	120.2
C5—N3—H3B	120.0	C8—C9—H9	120.2
H3A—N3—H3B	120.0	C9—C10—C11	122.5 (2)
O3—N5—O2	122.6 (3)	C9—C10—N5	118.2 (2)
O3—N5—C10	119.1 (3)	C11—C10—N5	119.3 (2)
O2—N5—C10	118.3 (2)	C12—C11—C10	117.8 (2)
C1—O1—C5	114.40 (17)	C12—C11—H11	121.1
C2—C1—N1	110.4 (2)	C10—C11—H11	121.1
C2—C1—O1	127.4 (2)	C11—C12—C13	120.8 (2)
N1—C1—O1	122.27 (19)	C11—C12—H12	119.6
C1—C2—C3	104.0 (2)	C13—C12—H12	119.6
C1—C2—C7	123.0 (2)	C12—C13—C8	121.1 (2)
C3—C2—C7	133.0 (2)	C12—C13—H13	119.5
N2—C3—C2	111.2 (2)	C8—C13—H13	119.5
N2—C3—C4	121.2 (2)	N4—C14—C6	175.8 (3)
C2—C3—C4	127.5 (2)	C16—C15—C20	120.0 (2)
C3—C4—H4A	109.5	C16—C15—N1	121.8 (2)
C3—C4—H4B	109.5	C20—C15—N1	118.1 (2)
H4A—C4—H4B	109.5	C15—C16—C17	119.5 (3)
C3—C4—H4C	109.5	C15—C16—H16	120.2
H4A—C4—H4C	109.5	C17—C16—H16	120.2
H4B—C4—H4C	109.5	C18—C17—C16	120.4 (3)
N3—C5—C6	127.4 (2)	C18—C17—H17	119.8
N3—C5—O1	109.72 (19)	C16—C17—H17	119.8
C6—C5—O1	122.9 (2)	C19—C18—C17	119.7 (3)
C5—C6—C14	118.6 (2)	C19—C18—H18	120.1
C5—C6—C7	125.7 (2)	C17—C18—H18	120.1
C14—C6—C7	115.70 (19)	C18—C19—C20	120.9 (3)
C2—C7—C6	106.39 (18)	C18—C19—H19	119.5
C2—C7—C8	112.92 (18)	C20—C19—H19	119.5
C6—C7—C8	111.56 (18)	C19—C20—C15	119.3 (3)
C2—C7—H7	108.6	C19—C20—H20	120.3
C6—C7—H7	108.6	C15—C20—H20	120.3
C8—C7—H7	108.6

C1—N1—N2—C3	0.1 (2)	C2—C7—C8—C9	−40.3 (3)
C15—N1—N2—C3	178.88 (19)	C6—C7—C8—C9	79.5 (2)
N2—N1—C1—C2	−0.1 (2)	C2—C7—C8—C13	141.2 (2)
C15—N1—C1—C2	−178.6 (2)	C6—C7—C8—C13	−99.0 (2)
N2—N1—C1—O1	−179.75 (18)	C13—C8—C9—C10	−0.2 (3)
C15—N1—C1—O1	1.7 (3)	C7—C8—C9—C10	−178.7 (2)
C5—O1—C1—C2	3.0 (3)	C8—C9—C10—C11	−0.3 (4)
C5—O1—C1—N1	−177.44 (18)	C8—C9—C10—N5	−179.3 (2)
N1—C1—C2—C3	0.1 (2)	O3—N5—C10—C9	−169.2 (2)
O1—C1—C2—C3	179.7 (2)	O2—N5—C10—C9	10.8 (3)
N1—C1—C2—C7	−178.24 (19)	O3—N5—C10—C11	11.8 (4)
O1—C1—C2—C7	1.4 (3)	O2—N5—C10—C11	−168.2 (3)
N1—N2—C3—C2	−0.1 (2)	C9—C10—C11—C12	0.3 (4)
N1—N2—C3—C4	178.7 (2)	N5—C10—C11—C12	179.3 (2)
C1—C2—C3—N2	0.0 (3)	C10—C11—C12—C13	0.3 (4)
C7—C2—C3—N2	178.1 (2)	C11—C12—C13—C8	−0.7 (4)
C1—C2—C3—C4	−178.7 (2)	C9—C8—C13—C12	0.7 (4)
C7—C2—C3—C4	−0.7 (4)	C7—C8—C13—C12	179.2 (2)
C1—O1—C5—N3	179.41 (18)	C5—C6—C14—N4	175 (4)
C1—O1—C5—C6	−2.0 (3)	C7—C6—C14—N4	−5 (4)
N3—C5—C6—C14	−4.0 (4)	C1—N1—C15—C16	13.3 (4)
O1—C5—C6—C14	177.69 (19)	N2—N1—C15—C16	−165.1 (2)
N3—C5—C6—C7	175.1 (2)	C1—N1—C15—C20	−167.8 (2)
O1—C5—C6—C7	−3.3 (3)	N2—N1—C15—C20	13.8 (3)
C1—C2—C7—C6	−5.6 (3)	C20—C15—C16—C17	−1.4 (4)
C3—C2—C7—C6	176.6 (2)	N1—C15—C16—C17	177.4 (2)
C1—C2—C7—C8	117.1 (2)	C15—C16—C17—C18	0.1 (4)
C3—C2—C7—C8	−60.7 (3)	C16—C17—C18—C19	1.3 (5)
C5—C6—C7—C2	6.7 (3)	C17—C18—C19—C20	−1.4 (5)
C14—C6—C7—C2	−174.27 (19)	C18—C19—C20—C15	0.0 (5)
C5—C6—C7—C8	−116.9 (2)	C16—C15—C20—C19	1.4 (4)
C14—C6—C7—C8	62.2 (2)	N1—C15—C20—C19	−177.5 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O2ⁱ	0.86	2.63	3.196 (3)	124
N3—H3B···N4ⁱⁱ	0.86	2.22	3.067 (3)	169
C19—H19···O2ⁱⁱⁱ	0.93	2.54	3.294 (4)	139

Symmetry codes: (i) x−1, y, z; (ii) x, −y+3/2, z+1/2; (iii) −x+2, y−1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₅N₅O₃
M_r	373.37
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	9.5089 (8), 13.9137 (11), 13.3747 (12)
β (°)	96.263 (1)
V (Å³)	1759.0 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.50 × 0.48 × 0.47

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2002)
T_min, T_max	0.952, 0.955
No. of measured, independent and observed [I > 2σ(I)] reflections	8659, 3087, 1961
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.121, 1.07
No. of reflections	3087
No. of parameters	255
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.17

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), 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
N3—H3A···O2ⁱ	0.86	2.63	3.196 (3)	124
N3—H3B···N4ⁱⁱ	0.86	2.22	3.067 (3)	169
C19—H19···O2ⁱⁱⁱ	0.93	2.54	3.294 (4)	139

Symmetry codes: (i) x−1, y, z; (ii) x, −y+3/2, z+1/2; (iii) −x+2, y−1/2, −z+3/2.

References

Bruker (2002). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chanda, A. & Fokin, V. V. (2009). Chem. Rev. 109, 725–748. Web of Science CrossRef PubMed CAS Google Scholar
El-Tamany, E. S., El-Shahed, F. A. & Mohamed, B. H. (1999). J. Serb. Chem. Soc. 64, 9–8. CAS Google Scholar
Foloppe, N., Fisher, L. M., Howes, R., Potter, A., Robertson Alan, G. S. & Surgenor, A. E. (2006). Bioorg. Med. Chem. 14, 4792–4802. Web of Science CrossRef PubMed CAS Google Scholar
Ismail, Z. H., Aly, G. M., El-Degwi, M. S., Heiba, H. I. & Ghorab, M. M. (2003). Egypt. J. Biotechnol. 13, 73–82. CAS Google Scholar
Junek, H. & Aigner, H. (1973). Chem. Ber. 106, 914–921. CrossRef CAS Google Scholar
Sharanin, Y. A., Sharanina, L. G. & Puzanova, V. V. (1983). Zh. Org. Khim. 19, 2609–2615. CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tejedor, D. & Garcia-Tellado, F. (2007). Chem. Soc. Rev. 36, 484–491. Web of Science CrossRef PubMed CAS Google Scholar
Vasuki, G. & Kumaravel, K. (2008). Tetrahedron Lett. 49, 5636–5638. Web of Science CSD CrossRef CAS Google Scholar
Wamhoff, H., Kroth, E. & Strauch, K. (1993). Synthesis, 11, 1129–1132. CrossRef CAS Google Scholar
Zaki, M. E. A., Soliman, H. A., Hiekal, O. A. & Rashad, A. E. (2006). Z. Naturforsch. Teil C, 61, 1–5. CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 6| June 2011| Pages o1454-o1455

doi:10.1107/S1600536811017387

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

6-Amino-3-methyl-4-(3-nitro­phen­yl)-1-phenyl-1H,4H-pyrano[2,3-c]pyrazole-5-carbo­nitrile

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

6-Amino-3-methyl-4-(3-nitrophenyl)-1-phenyl-1H,4H-pyrano[2,3-c]pyrazole-5-carbonitrile