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

Sabino, J.R.; Oliveira, C.M.A.; Fraga, C.A.M.; Barreiro, E.J.; Oliveira, V. de; Menegatti, R.

doi:10.1107/S1600536808037240

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page o2356

doi:10.1107/S1600536808037240

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

Jose R. Sabino,^a ^* Cecília M. A. Oliveira,^b Carlos A. M. Fraga,^c Eliezer J. Barreiro,^c Valéria de Oliveira ^d and Ricardo Menegatti ^d

^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 ); Menegatti et al. (2006 ); Barreiro et al. (2006 ).

Experimental

Crystal data

C₂₁H₁₃N₅O₄
M_r = 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)
R_int = 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
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	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 ); cell refinement: CAD-4-PC; 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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808037240/tk2318sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808037240/tk2318Isup2.hkl

checkCIF report

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···C25^iv: 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.

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

	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.
	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

C₂₁H₁₃N₅O₄	F(000) = 824
M_r = 399.36	D_x = 1.487 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 9.677 (2) Å	θ = 14.8–40.8°
b = 12.141 (3) Å	µ = 0.89 mm⁻¹
c = 17.438 (4) Å	T = 297 K
β = 119.451 (16)°	Prism, colourless
V = 1784.0 (8) Å³	0.3 × 0.1 × 0.08 mm
Z = 4

Data collection top

Enraf–Nonius CAD-4 diffractometer	θ_max = 67.9°, θ_min = 4.7°
Non–profiled ω/2ω scans	h = 0→11
3813 measured reflections	k = −14→1
3259 independent reflections	l = −20→18
2578 reflections with I > 2σ(I)	2 standard reflections every 120 min
R_int = 0.023	intensity decay: 1%

Refinement top

Refinement on F²	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ²(F_o²) + (0.152P)² + 0.0892P] where P = (F_o² + 2F_c²)/3
R[F² > 2σ(F²)] = 0.049	(Δ/σ)_max < 0.001
wR(F²) = 0.198	Δρ_max = 0.48 e Å⁻³
S = 1.07	Δρ_min = −0.38 e Å⁻³
3259 reflections	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
273 parameters	Extinction coefficient: 0.0114 (15)
0 restraints

Crystal data top

C₂₁H₁₃N₅O₄	V = 1784.0 (8) Å³
M_r = 399.36	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 9.677 (2) Å	µ = 0.89 mm⁻¹
b = 12.141 (3) Å	T = 297 K
c = 17.438 (4) Å	0.3 × 0.1 × 0.08 mm
β = 119.451 (16)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.023
3813 measured reflections	2 standard reflections every 120 min
3259 independent reflections	intensity decay: 1%
2578 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.198	H-atom parameters constrained
S = 1.07	Δρ_max = 0.48 e Å⁻³
3259 reflections	Δρ_min = −0.38 e Å⁻³
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

	x	y	z	U_iso*/U_eq
C3	−0.0408 (3)	0.00360 (19)	0.37884 (14)	0.0446 (5)
C4	0.1214 (3)	0.00403 (18)	0.44674 (14)	0.0425 (5)
C5	0.1708 (3)	−0.10707 (19)	0.45566 (14)	0.0431 (5)
C7	0.4230 (3)	−0.07508 (19)	0.56234 (16)	0.0500 (6)
H7	0.5254	−0.0987	0.6016	0.06*
C8	0.3874 (3)	0.03680 (18)	0.55955 (14)	0.0452 (5)
C9	0.4917 (3)	0.13014 (18)	0.61003 (15)	0.0455 (5)
C11	0.2390 (3)	0.19832 (18)	0.51522 (14)	0.0442 (5)
C12	0.2381 (3)	0.07694 (18)	0.50241 (14)	0.0427 (5)
C13	0.0263 (3)	−0.28159 (19)	0.37880 (16)	0.0462 (5)
C14	0.0917 (3)	−0.3569 (2)	0.44682 (16)	0.0514 (6)
H14	0.1508	−0.3332	0.5049	0.062*
C15	0.0681 (3)	−0.4684 (2)	0.42733 (19)	0.0584 (7)
H15	0.1132	−0.5198	0.4726	0.07*
C16	−0.0219 (3)	−0.5039 (2)	0.3414 (2)	0.0606 (7)
H16	−0.0394	−0.5787	0.3289	0.073*
C17	−0.0852 (3)	−0.4279 (2)	0.27450 (19)	0.0616 (7)
H17	−0.1454	−0.4516	0.2165	0.074*
C18	−0.0604 (3)	−0.3157 (2)	0.29235 (16)	0.0542 (6)
H18	−0.1016	−0.2645	0.2468	0.065*
C19	−0.1519 (3)	0.0984 (2)	0.34157 (17)	0.0549 (6)
H19A	−0.2592	0.0727	0.3172	0.082*
H19B	−0.1383	0.1329	0.2962	0.082*
H19C	−0.13	0.1509	0.3874	0.082*
C21	0.4456 (3)	0.33472 (18)	0.60655 (14)	0.0426 (5)
C22	0.3722 (3)	0.3988 (2)	0.64181 (16)	0.0489 (5)
H22	0.2948	0.3685	0.6523	0.059*
C23	0.4150 (3)	0.5083 (2)	0.66135 (16)	0.0507 (6)
H23	0.3682	0.5525	0.6859	0.061*
C24	0.5284 (3)	0.55016 (18)	0.64357 (14)	0.0461 (5)
C25	0.6055 (3)	0.4867 (2)	0.61069 (15)	0.0496 (6)
H25	0.6842	0.5169	0.6012	0.06*
C26	0.5631 (3)	0.37726 (19)	0.59215 (15)	0.0480 (5)
H26	0.6134	0.3325	0.5701	0.058*
O20	0.6301 (2)	0.12980 (14)	0.66441 (12)	0.0587 (5)
O27	0.1327 (2)	0.26369 (14)	0.47771 (13)	0.0592 (5)
O30	0.6424 (2)	0.70822 (16)	0.62526 (14)	0.0675 (6)
N1	0.0428 (2)	−0.16562 (16)	0.39668 (12)	0.0469 (5)
N2	−0.0858 (2)	−0.09733 (17)	0.34974 (13)	0.0497 (5)
N6	0.3155 (2)	−0.14946 (16)	0.51075 (13)	0.0489 (5)
N10	0.3932 (2)	0.22413 (15)	0.58107 (12)	0.0453 (5)
N28	0.5686 (3)	0.66741 (18)	0.65876 (13)	0.0561 (6)
O29	0.5258 (3)	0.71978 (17)	0.70287 (16)	0.0830 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C3	0.0414 (11)	0.0460 (11)	0.0430 (11)	0.0022 (9)	0.0181 (9)	0.0009 (9)
C4	0.0394 (11)	0.0436 (11)	0.0430 (11)	0.0017 (9)	0.0190 (9)	0.0022 (9)
C5	0.0401 (11)	0.0427 (11)	0.0459 (11)	0.0016 (9)	0.0207 (9)	0.0017 (9)
C7	0.0398 (11)	0.0408 (11)	0.0580 (13)	0.0049 (9)	0.0152 (10)	0.0057 (9)
C8	0.0418 (11)	0.0406 (11)	0.0479 (11)	0.0017 (9)	0.0180 (10)	0.0039 (9)
C9	0.0436 (12)	0.0393 (12)	0.0490 (12)	0.0048 (9)	0.0192 (10)	0.0033 (9)
C11	0.0407 (11)	0.0425 (12)	0.0464 (11)	0.0035 (9)	0.0191 (9)	0.0036 (9)
C12	0.0410 (11)	0.0411 (11)	0.0444 (11)	0.0046 (9)	0.0196 (9)	0.0045 (8)
C13	0.0411 (11)	0.0424 (12)	0.0567 (12)	−0.0020 (9)	0.0252 (10)	−0.0056 (9)
C14	0.0511 (13)	0.0476 (13)	0.0544 (13)	−0.0011 (10)	0.0250 (11)	−0.0023 (10)
C15	0.0586 (15)	0.0462 (13)	0.0755 (17)	0.0040 (11)	0.0368 (13)	0.0043 (12)
C16	0.0550 (14)	0.0457 (13)	0.0872 (19)	−0.0057 (11)	0.0397 (14)	−0.0145 (12)
C17	0.0524 (14)	0.0661 (17)	0.0650 (15)	−0.0068 (12)	0.0280 (12)	−0.0226 (13)
C18	0.0492 (13)	0.0567 (14)	0.0548 (13)	−0.0003 (11)	0.0241 (11)	−0.0034 (11)
C19	0.0426 (12)	0.0534 (14)	0.0545 (13)	0.0090 (10)	0.0130 (11)	0.0022 (10)
C21	0.0389 (11)	0.0386 (11)	0.0436 (10)	0.0011 (8)	0.0152 (9)	0.0014 (8)
C22	0.0469 (12)	0.0464 (12)	0.0550 (12)	−0.0016 (10)	0.0264 (11)	−0.0028 (10)
C23	0.0475 (12)	0.0483 (12)	0.0530 (12)	0.0023 (10)	0.0222 (10)	−0.0079 (10)
C24	0.0420 (11)	0.0390 (11)	0.0441 (11)	−0.0020 (9)	0.0109 (9)	−0.0046 (9)
C25	0.0441 (12)	0.0463 (12)	0.0581 (13)	−0.0018 (9)	0.0248 (11)	0.0008 (10)
C26	0.0454 (12)	0.0457 (12)	0.0528 (12)	0.0029 (10)	0.0241 (10)	−0.0026 (10)
O20	0.0414 (9)	0.0510 (10)	0.0623 (11)	0.0035 (7)	0.0089 (8)	0.0036 (7)
O27	0.0457 (9)	0.0434 (9)	0.0709 (11)	0.0100 (7)	0.0152 (8)	0.0002 (8)
O30	0.0607 (11)	0.0490 (10)	0.0811 (13)	−0.0093 (9)	0.0258 (10)	0.0001 (9)
N1	0.0415 (10)	0.0421 (10)	0.0497 (10)	−0.0009 (8)	0.0167 (8)	−0.0029 (8)
N2	0.0411 (10)	0.0498 (11)	0.0498 (10)	0.0019 (8)	0.0159 (9)	−0.0013 (8)
N6	0.0420 (10)	0.0395 (9)	0.0568 (11)	0.0039 (8)	0.0178 (9)	0.0014 (8)
N10	0.0408 (10)	0.0379 (10)	0.0493 (10)	0.0013 (8)	0.0161 (8)	0.0012 (7)
N28	0.0528 (12)	0.0460 (11)	0.0535 (11)	−0.0040 (9)	0.0139 (10)	−0.0058 (9)
O29	0.1122 (19)	0.0534 (11)	0.0905 (15)	−0.0043 (12)	0.0553 (15)	−0.0207 (10)

Geometric parameters (Å, º) top

C3—N2	1.316 (3)	C16—C17	1.373 (4)
C3—C4	1.428 (3)	C16—H16	0.93
C3—C19	1.489 (3)	C17—C18	1.392 (4)
C4—C12	1.387 (3)	C17—H17	0.93
C4—C5	1.414 (3)	C18—H18	0.93
C5—N6	1.351 (3)	C19—H19A	0.96
C5—N1	1.358 (3)	C19—H19B	0.96
C7—N6	1.337 (3)	C19—H19C	0.96
C7—C8	1.396 (3)	C21—C26	1.380 (3)
C7—H7	0.93	C21—C22	1.385 (3)
C8—C12	1.379 (3)	C21—N10	1.427 (3)
C8—C9	1.484 (3)	C22—C23	1.384 (3)
C9—O20	1.202 (3)	C22—H22	0.93
C9—N10	1.411 (3)	C23—C24	1.376 (4)
C11—O27	1.206 (3)	C23—H23	0.93
C11—N10	1.400 (3)	C24—C25	1.378 (3)
C11—C12	1.490 (3)	C24—N28	1.465 (3)
C13—C18	1.380 (3)	C25—C26	1.382 (3)
C13—C14	1.380 (3)	C25—H25	0.93
C13—N1	1.434 (3)	C26—H26	0.93
C14—C15	1.387 (3)	O30—N28	1.228 (3)
C14—H14	0.93	N1—N2	1.380 (3)
C15—C16	1.381 (4)	N28—O29	1.216 (3)
C15—H15	0.93

N2—C3—C4	110.1 (2)	C13—C18—C17	118.9 (2)
N2—C3—C19	121.4 (2)	C13—C18—H18	120.6
C4—C3—C19	128.5 (2)	C17—C18—H18	120.6
C12—C4—C5	114.68 (19)	C3—C19—H19A	109.5
C12—C4—C3	140.1 (2)	C3—C19—H19B	109.5
C5—C4—C3	105.19 (19)	H19A—C19—H19B	109.5
N6—C5—N1	125.4 (2)	C3—C19—H19C	109.5
N6—C5—C4	128.1 (2)	H19A—C19—H19C	109.5
N1—C5—C4	106.44 (19)	H19B—C19—H19C	109.5
N6—C7—C8	122.5 (2)	C26—C21—C22	121.3 (2)
N6—C7—H7	118.8	C26—C21—N10	119.6 (2)
C8—C7—H7	118.8	C22—C21—N10	119.1 (2)
C12—C8—C7	121.5 (2)	C23—C22—C21	119.5 (2)
C12—C8—C9	108.9 (2)	C23—C22—H22	120.2
C7—C8—C9	129.6 (2)	C21—C22—H22	120.2
O20—C9—N10	125.4 (2)	C24—C23—C22	118.3 (2)
O20—C9—C8	129.4 (2)	C24—C23—H23	120.8
N10—C9—C8	105.23 (18)	C22—C23—H23	120.8
O27—C11—N10	125.4 (2)	C23—C24—C25	122.8 (2)
O27—C11—C12	129.0 (2)	C23—C24—N28	119.2 (2)
N10—C11—C12	105.65 (18)	C25—C24—N28	117.9 (2)
C8—C12—C4	118.9 (2)	C24—C25—C26	118.4 (2)
C8—C12—C11	108.3 (2)	C24—C25—H25	120.8
C4—C12—C11	132.8 (2)	C26—C25—H25	120.8
C18—C13—C14	121.1 (2)	C21—C26—C25	119.6 (2)
C18—C13—N1	118.3 (2)	C21—C26—H26	120.2
C14—C13—N1	120.6 (2)	C25—C26—H26	120.2
C13—C14—C15	119.0 (2)	C5—N1—N2	110.82 (18)
C13—C14—H14	120.5	C5—N1—C13	129.86 (19)
C15—C14—H14	120.5	N2—N1—C13	119.32 (18)
C16—C15—C14	120.7 (2)	C3—N2—N1	107.44 (18)
C16—C15—H15	119.6	C7—N6—C5	114.4 (2)
C14—C15—H15	119.6	C11—N10—C9	111.87 (18)
C17—C16—C15	119.4 (2)	C11—N10—C21	122.56 (18)
C17—C16—H16	120.3	C9—N10—C21	125.15 (19)
C15—C16—H16	120.3	O29—N28—O30	123.2 (2)
C16—C17—C18	120.8 (3)	O29—N28—C24	118.7 (2)
C16—C17—H17	119.6	O30—N28—C24	118.1 (2)
C18—C17—H17	119.6

N2—C3—C4—C12	179.4 (3)	C22—C23—C24—N28	176.4 (2)
C19—C3—C4—C12	−0.2 (5)	C23—C24—C25—C26	2.2 (4)
N2—C3—C4—C5	0.3 (3)	N28—C24—C25—C26	−177.0 (2)
C19—C3—C4—C5	−179.4 (2)	C22—C21—C26—C25	−2.0 (3)
C12—C4—C5—N6	−0.3 (3)	N10—C21—C26—C25	175.2 (2)
C3—C4—C5—N6	179.1 (2)	C24—C25—C26—C21	0.2 (3)
C12—C4—C5—N1	−179.93 (19)	N6—C5—N1—N2	−179.1 (2)
C3—C4—C5—N1	−0.5 (2)	C4—C5—N1—N2	0.6 (2)
N6—C7—C8—C12	−0.4 (4)	N6—C5—N1—C13	1.1 (4)
N6—C7—C8—C9	−178.5 (2)	C4—C5—N1—C13	−179.2 (2)
C12—C8—C9—O20	−178.1 (3)	C18—C13—N1—C5	−140.1 (2)
C7—C8—C9—O20	0.2 (4)	C14—C13—N1—C5	41.9 (4)
C12—C8—C9—N10	2.0 (3)	C18—C13—N1—N2	40.1 (3)
C7—C8—C9—N10	−179.7 (2)	C14—C13—N1—N2	−137.9 (2)
C7—C8—C12—C4	0.0 (3)	C4—C3—N2—N1	0.1 (3)
C9—C8—C12—C4	178.5 (2)	C19—C3—N2—N1	179.8 (2)
C7—C8—C12—C11	−179.7 (2)	C5—N1—N2—C3	−0.4 (3)
C9—C8—C12—C11	−1.2 (2)	C13—N1—N2—C3	179.4 (2)
C5—C4—C12—C8	0.3 (3)	C8—C7—N6—C5	0.4 (4)
C3—C4—C12—C8	−178.8 (3)	N1—C5—N6—C7	179.5 (2)
C5—C4—C12—C11	179.9 (2)	C4—C5—N6—C7	−0.1 (4)
C3—C4—C12—C11	0.9 (5)	O27—C11—N10—C9	−178.1 (2)
O27—C11—C12—C8	179.4 (2)	C12—C11—N10—C9	1.3 (2)
N10—C11—C12—C8	0.0 (2)	O27—C11—N10—C21	−5.2 (4)
O27—C11—C12—C4	−0.3 (4)	C12—C11—N10—C21	174.2 (2)
N10—C11—C12—C4	−179.6 (2)	O20—C9—N10—C11	178.1 (2)
C18—C13—C14—C15	−0.5 (4)	C8—C9—N10—C11	−2.0 (3)
N1—C13—C14—C15	177.4 (2)	O20—C9—N10—C21	5.4 (4)
C13—C14—C15—C16	−1.1 (4)	C8—C9—N10—C21	−174.7 (2)
C14—C15—C16—C17	1.5 (4)	C26—C21—N10—C11	−115.1 (2)
C15—C16—C17—C18	−0.3 (4)	C22—C21—N10—C11	62.1 (3)
C14—C13—C18—C17	1.8 (4)	C26—C21—N10—C9	56.9 (3)
N1—C13—C18—C17	−176.2 (2)	C22—C21—N10—C9	−125.9 (2)
C16—C17—C18—C13	−1.4 (4)	C23—C24—N28—O29	14.8 (3)
C26—C21—C22—C23	1.4 (4)	C25—C24—N28—O29	−166.1 (2)
N10—C21—C22—C23	−175.8 (2)	C23—C24—N28—O30	−164.4 (2)
C21—C22—C23—C24	1.0 (4)	C25—C24—N28—O30	14.8 (3)
C22—C23—C24—C25	−2.8 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	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+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₂₁H₁₃N₅O₄
M_r	399.36
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	297
a, b, c (Å)	9.677 (2), 12.141 (3), 17.438 (4)
β (°)	119.451 (16)
V (Å³)	1784.0 (8)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.89
Crystal size (mm)	0.3 × 0.1 × 0.08

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	3813, 3259, 2578
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.601

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.198, 1.07
No. of reflections	3259
No. of parameters	273
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	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—N2	1.316 (3)	C8—C9	1.484 (3)
C3—C4	1.428 (3)	C11—C12	1.490 (3)
C4—C12	1.387 (3)	O30—N28	1.228 (3)
C7—N6	1.337 (3)	N28—O29	1.216 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	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+1/2, z−1/2.

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

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. Google Scholar
Carneiro, E. O., De Oliveira, V., Menegatti, R., Fraga, C. A. M. & Barreiro, E. J. L. (2005). Rev. Electron. Farm. 2, 44–47. Google Scholar
Enraf–Nonius (1993). CAD-4-PC. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4-PC. University of Marburg, Germany. Google Scholar
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. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 64| Part 12| December 2008| Page o2356

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

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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