1-Methyl-7-(4-nitro-phen-yl)-3-phenyl-pyrazolo[3,4-b]pyrrolo[3,4-d]pyridine-6,8(3H,7H)-dione.

In the title compound, C(21)H(13)N(5)O(4), the dihedral angles formed between the planes of the phenyl and nitro-phenyl 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 = 399.36

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 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

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 ▶).

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C21H13N5O4	F000 = 824
Mr = 399.36	Dx = 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 = 14.8–40.8º
b = 12.141 (3) Å	µ = 0.89 mm−1
c = 17.438 (4) Å	T = 297 (2) K
β = 119.451 (16)º	Prism, colourless
V = 1784.0 (8) Å3	0.3 × 0.1 × 0.08 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	θmax = 67.9º
T = 297(2) K	θmin = 4.7º
Non–profiled ω/2ω scans	h = 0→11
Absorption correction: none	k = −14→1
3813 measured reflections	l = −20→18
3259 independent reflections	2 standard reflections
2578 reflections with I > 2σ(I)	every 120 min
Rint = 0.023	intensity decay: 1%

Refinement on F2	H-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) = 0.198	Δρmax = 0.48 e Å−3
S = 1.07	Δρmin = −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)

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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

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) ; (ii) .