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ISSN: 2056-9890

1-Methyl-7-(4-nitro­phen­yl)-3-phenyl­pyrazolo[3,4-b]pyrrolo[3,4-d]pyridine-6,8(3H,7H)-dione

aInstituto de Física, Universidade Federal de Goiás, Caixa Postal 131, 74001-970, Goiânia, GO, Brazil, bInstituto de Química, Universidade Federal de Goiás, Caixa Postal 131, 74001-970, Goiânia, GO, Brazil, cLaboratory of Evaluation and Synthesis of Bioactive Substances, (LASSBio), Faculdade de Farmácia, Universidade Federal do Rio de Janeiro, Caixa Postal 68023, 21944-971, Rio de Janeiro, RJ, Brazil, and dFaculdade de Farmácia, Universidade Federal de Goiás, Caixa Postal 131, 74001-970, Goiânia, GO, Brazil
*Correspondence e-mail: jrsabino@if.ufg.br

(Received 20 October 2008; accepted 10 November 2008; online 13 November 2008)

In the title compound, C21H13N5O4, the dihedral angles formed between the planes of the phenyl and nitro­phenyl rings and that of the heterotricyclic plane are 41.29 (7) and 61.35 (6)°, respectively. In the crystal, weak C—H⋯O interactions help to establish the packing.

Related literature

For background, see: Carneiro et al. (2005[Carneiro, E. O., De Oliveira, V., Menegatti, R., Fraga, C. A. M. & Barreiro, E. J. L. (2005). Rev. Electron. Farm. 2, 44-47.]); Menegatti et al. (2006[Menegatti, R., Silva, G. M. S., Zapata-Sudo, G., Raimundo, J. M., Sudo, R. T., Barreiro, E. J. & Fraga, C. A. M. (2006). Bioorg. Med. Chem. 14, 632-640.]); Barreiro et al. (2006[Barreiro, E. J. L., Fraga, C. A. M., Sudo, G. Z., Sudo, R. T. & Menegatti, R. (2006). WO Patent 092 032 A3, September 8, 2006.]).

[Scheme 1]

Experimental

Crystal data
  • C21H13N5O4

  • Mr = 399.36

  • Monoclinic, P 21 /c

  • a = 9.677 (2) Å

  • b = 12.141 (3) Å

  • c = 17.438 (4) Å

  • β = 119.451 (16)°

  • V = 1784.0 (8) Å3

  • Z = 4

  • Cu Kα radiation

  • μ = 0.89 mm−1

  • T = 297 (2) K

  • 0.3 × 0.1 × 0.08 mm

Data collection
  • Enraf–Nonius CAD-4 diffractometer

  • Absorption correction: none

  • 3813 measured reflections

  • 3259 independent reflections

  • 2578 reflections with I > 2σ(I)

  • Rint = 0.023

  • 2 standard reflections frequency: 120 min intensity decay: 1%

Refinement
  • R[F2 > 2σ(F2)] = 0.049

  • wR(F2) = 0.198

  • S = 1.07

  • 3259 reflections

  • 273 parameters

  • H-atom parameters constrained

  • Δρmax = 0.48 e Å−3

  • Δρmin = −0.38 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C7—H7⋯O30i 0.93 2.55 3.216 (3) 129
C18—H18⋯O30ii 0.93 2.44 3.197 (3) 139
Symmetry codes: (i) x, y-1, z; (ii) [x-1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: CAD-4-PC (Enraf–Nonius, 1993[Enraf-Nonius (1993). CAD-4-PC. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4-PC; data reduction: XCAD4 (Harms & Wocadlo, 1995[Harms, K. & Wocadlo, S. (1995). XCAD4-PC. University of Marburg, Germany.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

Supporting information


Comment top

The title compound (I) (Carneiro et al., 2005; Menegatti et al., 2006; Barreiro et al., 2006) features a novel functionalized three-fused rings skeleton, Fig. 1. The bond distances within the pyridine ring are consistent with aromatic delocalization but the pyrazole ring presents a double bond, Table 1. The C8—C9 and C11—C12 bond lengths are elongated from the expected distances by 0.025 and 0.03 Å, respectively.

The pyrazolo[3,4-b]pyrrolo[3,4-d]pyridine moiety is planar (plane α, with r.m.s. deviation of about 0.01 Å). Relative to plane α, the phenyl rings C21/C26 and C13/C18 form dihedral angles of 41.29 (7)° and 61.35 (6)°, respectively. The latter ring is slanted from the plane α so that the C21 and C24 atoms are shifted by 0.118 (3) and 0.436 (4) Å from the plane α, respectively. This might be in part due to the participation of the oxygen atom O30 in two C-H···O contacts, C7—H7···O30i and C18—H18···O30ii; see Table 2 for details. The former interaction connects molecules into a linear chain along the b-axis and the latter connects parallel chains to form sheets in the plane of approximate indices (-1 0 2). The molecules in the linear chains interact with centrosymmetrically related chains via π···π stacking [closest distance for C25···C25iv: 3.380 (5) Å; (iv): 1 - x, 1 - y, 1 - z]. In addition, molecules participate in a C—H···π interaction: C25—H25···C15iii [2.74 Å, 3.539 (4) Å, 144°; (iii) 1 -x, -y, 1 -z] to consolidate the crystal packing, Fig. 2.

Related literature top

For background, see: Carneiro et al. (2005); Menegatti et al. (2006); Barreiro et al. (2006).

Experimental top

Compound (I) was synthesized as described previously (Menegatti et al., 2006). A colourless needle for crystallography was obtained by slow evaporation of a MeOH solution of (I) at room temperature.

Refinement top

All H atoms were positioned in idealized positions in the riding model approximation with C—H = 0.93 - 0.96 Å, and with Uiso(H) = 1.2-1.5 Ueq(C).

Computing details top

Data collection: CAD-4-PC (Enraf–Nonius, 1993); cell refinement: CAD-4-PC (Enraf–Nonius, 1993); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. View of (I) with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.
[Figure 2] Fig. 2. Packing diagram of (I). Intermolecular interactions are shown as dashed lines. Only the H atoms involved in intermolecular contacts are shown.
1-Methyl-7-(4-nitrophenyl)-3-phenylpyrazolo[3,4-b]pyrrolo[3,4- d]pyridine-6,8(3H,7H)-dione top
Crystal data top
C21H13N5O4F(000) = 824
Mr = 399.36Dx = 1.487 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.5418 Å
Hall symbol: -P 2ybcCell parameters from 25 reflections
a = 9.677 (2) Åθ = 14.8–40.8°
b = 12.141 (3) ŵ = 0.89 mm1
c = 17.438 (4) ÅT = 297 K
β = 119.451 (16)°Prism, colourless
V = 1784.0 (8) Å30.3 × 0.1 × 0.08 mm
Z = 4
Data collection top
Enraf–Nonius CAD-4
diffractometer
θmax = 67.9°, θmin = 4.7°
Non–profiled ω/2ω scansh = 011
3813 measured reflectionsk = 141
3259 independent reflectionsl = 2018
2578 reflections with I > 2σ(I)2 standard reflections every 120 min
Rint = 0.023 intensity decay: 1%
Refinement top
Refinement on F2H-atom parameters constrained
Least-squares matrix: full w = 1/[σ2(Fo2) + (0.152P)2 + 0.0892P]
where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.049(Δ/σ)max < 0.001
wR(F2) = 0.198Δρmax = 0.48 e Å3
S = 1.07Δρmin = 0.38 e Å3
3259 reflectionsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
273 parametersExtinction coefficient: 0.0114 (15)
0 restraints
Crystal data top
C21H13N5O4V = 1784.0 (8) Å3
Mr = 399.36Z = 4
Monoclinic, P21/cCu Kα radiation
a = 9.677 (2) ŵ = 0.89 mm1
b = 12.141 (3) ÅT = 297 K
c = 17.438 (4) Å0.3 × 0.1 × 0.08 mm
β = 119.451 (16)°
Data collection top
Enraf–Nonius CAD-4
diffractometer
Rint = 0.023
3813 measured reflections2 standard reflections every 120 min
3259 independent reflections intensity decay: 1%
2578 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0490 restraints
wR(F2) = 0.198H-atom parameters constrained
S = 1.07Δρmax = 0.48 e Å3
3259 reflectionsΔρmin = 0.38 e Å3
273 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C30.0408 (3)0.00360 (19)0.37884 (14)0.0446 (5)
C40.1214 (3)0.00403 (18)0.44674 (14)0.0425 (5)
C50.1708 (3)0.10707 (19)0.45566 (14)0.0431 (5)
C70.4230 (3)0.07508 (19)0.56234 (16)0.0500 (6)
H70.52540.09870.60160.06*
C80.3874 (3)0.03680 (18)0.55955 (14)0.0452 (5)
C90.4917 (3)0.13014 (18)0.61003 (15)0.0455 (5)
C110.2390 (3)0.19832 (18)0.51522 (14)0.0442 (5)
C120.2381 (3)0.07694 (18)0.50241 (14)0.0427 (5)
C130.0263 (3)0.28159 (19)0.37880 (16)0.0462 (5)
C140.0917 (3)0.3569 (2)0.44682 (16)0.0514 (6)
H140.15080.33320.50490.062*
C150.0681 (3)0.4684 (2)0.42733 (19)0.0584 (7)
H150.11320.51980.47260.07*
C160.0219 (3)0.5039 (2)0.3414 (2)0.0606 (7)
H160.03940.57870.32890.073*
C170.0852 (3)0.4279 (2)0.27450 (19)0.0616 (7)
H170.14540.45160.21650.074*
C180.0604 (3)0.3157 (2)0.29235 (16)0.0542 (6)
H180.10160.26450.24680.065*
C190.1519 (3)0.0984 (2)0.34157 (17)0.0549 (6)
H19A0.25920.07270.31720.082*
H19B0.13830.13290.29620.082*
H19C0.130.15090.38740.082*
C210.4456 (3)0.33472 (18)0.60655 (14)0.0426 (5)
C220.3722 (3)0.3988 (2)0.64181 (16)0.0489 (5)
H220.29480.36850.65230.059*
C230.4150 (3)0.5083 (2)0.66135 (16)0.0507 (6)
H230.36820.55250.68590.061*
C240.5284 (3)0.55016 (18)0.64357 (14)0.0461 (5)
C250.6055 (3)0.4867 (2)0.61069 (15)0.0496 (6)
H250.68420.51690.60120.06*
C260.5631 (3)0.37726 (19)0.59215 (15)0.0480 (5)
H260.61340.33250.57010.058*
O200.6301 (2)0.12980 (14)0.66441 (12)0.0587 (5)
O270.1327 (2)0.26369 (14)0.47771 (13)0.0592 (5)
O300.6424 (2)0.70822 (16)0.62526 (14)0.0675 (6)
N10.0428 (2)0.16562 (16)0.39668 (12)0.0469 (5)
N20.0858 (2)0.09733 (17)0.34974 (13)0.0497 (5)
N60.3155 (2)0.14946 (16)0.51075 (13)0.0489 (5)
N100.3932 (2)0.22413 (15)0.58107 (12)0.0453 (5)
N280.5686 (3)0.66741 (18)0.65876 (13)0.0561 (6)
O290.5258 (3)0.71978 (17)0.70287 (16)0.0830 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C30.0414 (11)0.0460 (11)0.0430 (11)0.0022 (9)0.0181 (9)0.0009 (9)
C40.0394 (11)0.0436 (11)0.0430 (11)0.0017 (9)0.0190 (9)0.0022 (9)
C50.0401 (11)0.0427 (11)0.0459 (11)0.0016 (9)0.0207 (9)0.0017 (9)
C70.0398 (11)0.0408 (11)0.0580 (13)0.0049 (9)0.0152 (10)0.0057 (9)
C80.0418 (11)0.0406 (11)0.0479 (11)0.0017 (9)0.0180 (10)0.0039 (9)
C90.0436 (12)0.0393 (12)0.0490 (12)0.0048 (9)0.0192 (10)0.0033 (9)
C110.0407 (11)0.0425 (12)0.0464 (11)0.0035 (9)0.0191 (9)0.0036 (9)
C120.0410 (11)0.0411 (11)0.0444 (11)0.0046 (9)0.0196 (9)0.0045 (8)
C130.0411 (11)0.0424 (12)0.0567 (12)0.0020 (9)0.0252 (10)0.0056 (9)
C140.0511 (13)0.0476 (13)0.0544 (13)0.0011 (10)0.0250 (11)0.0023 (10)
C150.0586 (15)0.0462 (13)0.0755 (17)0.0040 (11)0.0368 (13)0.0043 (12)
C160.0550 (14)0.0457 (13)0.0872 (19)0.0057 (11)0.0397 (14)0.0145 (12)
C170.0524 (14)0.0661 (17)0.0650 (15)0.0068 (12)0.0280 (12)0.0226 (13)
C180.0492 (13)0.0567 (14)0.0548 (13)0.0003 (11)0.0241 (11)0.0034 (11)
C190.0426 (12)0.0534 (14)0.0545 (13)0.0090 (10)0.0130 (11)0.0022 (10)
C210.0389 (11)0.0386 (11)0.0436 (10)0.0011 (8)0.0152 (9)0.0014 (8)
C220.0469 (12)0.0464 (12)0.0550 (12)0.0016 (10)0.0264 (11)0.0028 (10)
C230.0475 (12)0.0483 (12)0.0530 (12)0.0023 (10)0.0222 (10)0.0079 (10)
C240.0420 (11)0.0390 (11)0.0441 (11)0.0020 (9)0.0109 (9)0.0046 (9)
C250.0441 (12)0.0463 (12)0.0581 (13)0.0018 (9)0.0248 (11)0.0008 (10)
C260.0454 (12)0.0457 (12)0.0528 (12)0.0029 (10)0.0241 (10)0.0026 (10)
O200.0414 (9)0.0510 (10)0.0623 (11)0.0035 (7)0.0089 (8)0.0036 (7)
O270.0457 (9)0.0434 (9)0.0709 (11)0.0100 (7)0.0152 (8)0.0002 (8)
O300.0607 (11)0.0490 (10)0.0811 (13)0.0093 (9)0.0258 (10)0.0001 (9)
N10.0415 (10)0.0421 (10)0.0497 (10)0.0009 (8)0.0167 (8)0.0029 (8)
N20.0411 (10)0.0498 (11)0.0498 (10)0.0019 (8)0.0159 (9)0.0013 (8)
N60.0420 (10)0.0395 (9)0.0568 (11)0.0039 (8)0.0178 (9)0.0014 (8)
N100.0408 (10)0.0379 (10)0.0493 (10)0.0013 (8)0.0161 (8)0.0012 (7)
N280.0528 (12)0.0460 (11)0.0535 (11)0.0040 (9)0.0139 (10)0.0058 (9)
O290.1122 (19)0.0534 (11)0.0905 (15)0.0043 (12)0.0553 (15)0.0207 (10)
Geometric parameters (Å, º) top
C3—N21.316 (3)C16—C171.373 (4)
C3—C41.428 (3)C16—H160.93
C3—C191.489 (3)C17—C181.392 (4)
C4—C121.387 (3)C17—H170.93
C4—C51.414 (3)C18—H180.93
C5—N61.351 (3)C19—H19A0.96
C5—N11.358 (3)C19—H19B0.96
C7—N61.337 (3)C19—H19C0.96
C7—C81.396 (3)C21—C261.380 (3)
C7—H70.93C21—C221.385 (3)
C8—C121.379 (3)C21—N101.427 (3)
C8—C91.484 (3)C22—C231.384 (3)
C9—O201.202 (3)C22—H220.93
C9—N101.411 (3)C23—C241.376 (4)
C11—O271.206 (3)C23—H230.93
C11—N101.400 (3)C24—C251.378 (3)
C11—C121.490 (3)C24—N281.465 (3)
C13—C181.380 (3)C25—C261.382 (3)
C13—C141.380 (3)C25—H250.93
C13—N11.434 (3)C26—H260.93
C14—C151.387 (3)O30—N281.228 (3)
C14—H140.93N1—N21.380 (3)
C15—C161.381 (4)N28—O291.216 (3)
C15—H150.93
N2—C3—C4110.1 (2)C13—C18—C17118.9 (2)
N2—C3—C19121.4 (2)C13—C18—H18120.6
C4—C3—C19128.5 (2)C17—C18—H18120.6
C12—C4—C5114.68 (19)C3—C19—H19A109.5
C12—C4—C3140.1 (2)C3—C19—H19B109.5
C5—C4—C3105.19 (19)H19A—C19—H19B109.5
N6—C5—N1125.4 (2)C3—C19—H19C109.5
N6—C5—C4128.1 (2)H19A—C19—H19C109.5
N1—C5—C4106.44 (19)H19B—C19—H19C109.5
N6—C7—C8122.5 (2)C26—C21—C22121.3 (2)
N6—C7—H7118.8C26—C21—N10119.6 (2)
C8—C7—H7118.8C22—C21—N10119.1 (2)
C12—C8—C7121.5 (2)C23—C22—C21119.5 (2)
C12—C8—C9108.9 (2)C23—C22—H22120.2
C7—C8—C9129.6 (2)C21—C22—H22120.2
O20—C9—N10125.4 (2)C24—C23—C22118.3 (2)
O20—C9—C8129.4 (2)C24—C23—H23120.8
N10—C9—C8105.23 (18)C22—C23—H23120.8
O27—C11—N10125.4 (2)C23—C24—C25122.8 (2)
O27—C11—C12129.0 (2)C23—C24—N28119.2 (2)
N10—C11—C12105.65 (18)C25—C24—N28117.9 (2)
C8—C12—C4118.9 (2)C24—C25—C26118.4 (2)
C8—C12—C11108.3 (2)C24—C25—H25120.8
C4—C12—C11132.8 (2)C26—C25—H25120.8
C18—C13—C14121.1 (2)C21—C26—C25119.6 (2)
C18—C13—N1118.3 (2)C21—C26—H26120.2
C14—C13—N1120.6 (2)C25—C26—H26120.2
C13—C14—C15119.0 (2)C5—N1—N2110.82 (18)
C13—C14—H14120.5C5—N1—C13129.86 (19)
C15—C14—H14120.5N2—N1—C13119.32 (18)
C16—C15—C14120.7 (2)C3—N2—N1107.44 (18)
C16—C15—H15119.6C7—N6—C5114.4 (2)
C14—C15—H15119.6C11—N10—C9111.87 (18)
C17—C16—C15119.4 (2)C11—N10—C21122.56 (18)
C17—C16—H16120.3C9—N10—C21125.15 (19)
C15—C16—H16120.3O29—N28—O30123.2 (2)
C16—C17—C18120.8 (3)O29—N28—C24118.7 (2)
C16—C17—H17119.6O30—N28—C24118.1 (2)
C18—C17—H17119.6
N2—C3—C4—C12179.4 (3)C22—C23—C24—N28176.4 (2)
C19—C3—C4—C120.2 (5)C23—C24—C25—C262.2 (4)
N2—C3—C4—C50.3 (3)N28—C24—C25—C26177.0 (2)
C19—C3—C4—C5179.4 (2)C22—C21—C26—C252.0 (3)
C12—C4—C5—N60.3 (3)N10—C21—C26—C25175.2 (2)
C3—C4—C5—N6179.1 (2)C24—C25—C26—C210.2 (3)
C12—C4—C5—N1179.93 (19)N6—C5—N1—N2179.1 (2)
C3—C4—C5—N10.5 (2)C4—C5—N1—N20.6 (2)
N6—C7—C8—C120.4 (4)N6—C5—N1—C131.1 (4)
N6—C7—C8—C9178.5 (2)C4—C5—N1—C13179.2 (2)
C12—C8—C9—O20178.1 (3)C18—C13—N1—C5140.1 (2)
C7—C8—C9—O200.2 (4)C14—C13—N1—C541.9 (4)
C12—C8—C9—N102.0 (3)C18—C13—N1—N240.1 (3)
C7—C8—C9—N10179.7 (2)C14—C13—N1—N2137.9 (2)
C7—C8—C12—C40.0 (3)C4—C3—N2—N10.1 (3)
C9—C8—C12—C4178.5 (2)C19—C3—N2—N1179.8 (2)
C7—C8—C12—C11179.7 (2)C5—N1—N2—C30.4 (3)
C9—C8—C12—C111.2 (2)C13—N1—N2—C3179.4 (2)
C5—C4—C12—C80.3 (3)C8—C7—N6—C50.4 (4)
C3—C4—C12—C8178.8 (3)N1—C5—N6—C7179.5 (2)
C5—C4—C12—C11179.9 (2)C4—C5—N6—C70.1 (4)
C3—C4—C12—C110.9 (5)O27—C11—N10—C9178.1 (2)
O27—C11—C12—C8179.4 (2)C12—C11—N10—C91.3 (2)
N10—C11—C12—C80.0 (2)O27—C11—N10—C215.2 (4)
O27—C11—C12—C40.3 (4)C12—C11—N10—C21174.2 (2)
N10—C11—C12—C4179.6 (2)O20—C9—N10—C11178.1 (2)
C18—C13—C14—C150.5 (4)C8—C9—N10—C112.0 (3)
N1—C13—C14—C15177.4 (2)O20—C9—N10—C215.4 (4)
C13—C14—C15—C161.1 (4)C8—C9—N10—C21174.7 (2)
C14—C15—C16—C171.5 (4)C26—C21—N10—C11115.1 (2)
C15—C16—C17—C180.3 (4)C22—C21—N10—C1162.1 (3)
C14—C13—C18—C171.8 (4)C26—C21—N10—C956.9 (3)
N1—C13—C18—C17176.2 (2)C22—C21—N10—C9125.9 (2)
C16—C17—C18—C131.4 (4)C23—C24—N28—O2914.8 (3)
C26—C21—C22—C231.4 (4)C25—C24—N28—O29166.1 (2)
N10—C21—C22—C23175.8 (2)C23—C24—N28—O30164.4 (2)
C21—C22—C23—C241.0 (4)C25—C24—N28—O3014.8 (3)
C22—C23—C24—C252.8 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H7···O30i0.932.553.216 (3)129
C18—H18···O30ii0.932.443.197 (3)139
Symmetry codes: (i) x, y1, z; (ii) x1, y+1/2, z1/2.

Experimental details

Crystal data
Chemical formulaC21H13N5O4
Mr399.36
Crystal system, space groupMonoclinic, P21/c
Temperature (K)297
a, b, c (Å)9.677 (2), 12.141 (3), 17.438 (4)
β (°) 119.451 (16)
V3)1784.0 (8)
Z4
Radiation typeCu Kα
µ (mm1)0.89
Crystal size (mm)0.3 × 0.1 × 0.08
Data collection
DiffractometerEnraf–Nonius CAD-4
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
3813, 3259, 2578
Rint0.023
(sin θ/λ)max1)0.601
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.198, 1.07
No. of reflections3259
No. of parameters273
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.48, 0.38

Computer programs: CAD-4-PC (Enraf–Nonius, 1993), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003), WinGX (Farrugia, 1999).

Selected bond lengths (Å) top
C3—N21.316 (3)C8—C91.484 (3)
C3—C41.428 (3)C11—C121.490 (3)
C4—C121.387 (3)O30—N281.228 (3)
C7—N61.337 (3)N28—O291.216 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H7···O30i0.932.553.216 (3)129
C18—H18···O30ii0.932.443.197 (3)139
Symmetry codes: (i) x, y1, z; (ii) x1, y+1/2, z1/2.
 

Acknowledgements

The authors gratefully acknowledge the financial support of Conselho Nacional de Desenvolvimento Científico e Tecnológico - CNPq, Pró-Reitoria de Pesquisa e Pós Graduação-PRPPG/UFG.

References

First citationBarreiro, E. J. L., Fraga, C. A. M., Sudo, G. Z., Sudo, R. T. & Menegatti, R. (2006). WO Patent 092 032 A3, September 8, 2006.  Google Scholar
First citationCarneiro, E. O., De Oliveira, V., Menegatti, R., Fraga, C. A. M. & Barreiro, E. J. L. (2005). Rev. Electron. Farm. 2, 44–47.  Google Scholar
First citationEnraf–Nonius (1993). CAD-4-PC. Enraf–Nonius, Delft, The Netherlands.  Google Scholar
First citationFarrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.  CrossRef CAS IUCr Journals Google Scholar
First citationHarms, K. & Wocadlo, S. (1995). XCAD4-PC. University of Marburg, Germany.  Google Scholar
First citationMenegatti, R., Silva, G. M. S., Zapata-Sudo, G., Raimundo, J. M., Sudo, R. T., Barreiro, E. J. & Fraga, C. A. M. (2006). Bioorg. Med. Chem. 14, 632–640.  Web of Science CrossRef PubMed CAS Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2003). J. Appl. Cryst. 36, 7–13.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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