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

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

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

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.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536808037240/tk2318sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536808037240/tk2318Isup2.hkl Contains datablock I

CCDC reference: 712461

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Key indicators

Single-crystal X-ray study
T = 297 K
Mean (C-C) = 0.003 Å
R factor = 0.049
wR factor = 0.198
Data-to-parameter ratio = 11.9

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No syntax errors found



Alert level C
            Value of measurement temperature given =   297.000
            Value of melting point given =     0.000
SHFSU01_ALERT_2_C  Test not performed. _refine_ls_shift/su_max and
            _refine_ls_shift/esd_max not present.
            Absolute value of the parameter shift to su ratio given   0.001

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check


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Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

Author Response: The authors contributions were as follows:

 JRS: x-rays diffraction study
 CMAO: cristalization
 VO: Bioconversion assays
 RM: chemical synthesys
 CAMF: molecular modelling methods (CoMFA)
 EJB: pharmacological assays



   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

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)