Nevirapininium picrate

Harrison, W.T.A.; Sreevidya, T.V.; Narayana, B.; Sarojini, B.K.; Yathirajan, H.S.

doi:10.1107/S1600536807040731

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Nevirapininium picrate

W. T. A. Harrison, T. V. Sreevidya, B. Narayana, B. K. Sarojini and H. S. Yathirajan

The title compound, C₁₅H₁₅N₄O⁺·C₆H₂N₃O₇⁻, is the picrate salt of nevirapine, in which the cation and anion are linked by an N—H

O hydrogen bond. A second N—H

O interaction leads to centrosymmetric dimers of cations. The dihedral angle between the aromatic ring planes in the cation is 48.27 (8)°.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807040731/lw2026sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807040731/lw2026Isup2.hkl Contains datablock I

CCDC reference: 660334

checkCIF report

Key indicators

Single-crystal X-ray study
T = 291 K
Mean (C-C) = 0.002 Å
R factor = 0.042
wR factor = 0.120
Data-to-parameter ratio = 14.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)        100 Deg.
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          3
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N11    -   C22     ..       5.47 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C15
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        N11

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

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 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

Comment top

Nevirapine, C₁₅H₁₄N₄O, has several important biological applications: it is a non-nucleoside reverse transcriptase inhibitor (NNRTI) used to treat HIV-1 infection and AIDS (Bartlett, 2005) and it is an inducer of cytochrome P450 isoenzymes CYP3A4 and CYP2B6 (Gazzard, 2005). Nevirapine in triple combination therapy has been shown to suppress viral load effectively when used as initial antiretroviral therapy (Manosuthi et al., 2007).

The crystal structure of nevirapine was described earlier (Mui et al., 1992). In continuation of our work on the structures of pharmaceutical compounds (Harrison, Ashok et al., 2007; Harrison, Bindya et al., 2007), we now report the crystal structure of the title compound, (I), a molecular salt of nevirapine and picric acid.

The structure of (I) (Fig. 1) shows that proton transfer from picric acid (pa) to nevirapine (np) has occurred, and that the N atom of the methyl-substituted pyridine ring has been protonated. The dihedral angle between the C1—C5/N1 and C7—C11/N4 ring planes is 48.27 (8)°, which is substantially different to the equivalent value of 59° (no s.u. stated) for unprotonated nevirapine (Mui et al., 1992). This difference may arise due to the flexibility of the central seven-membered ring. In (I), the bond-angle sum about N2 (350.6°) is ambiguous with respect to the hybridization of the nitrogen atom. The equivalent value for N3 (358.3°) equates to sp² hybridization, perhaps due to delocalization with the adjacent pyridine ring (Mui et al., 1992).

The significant variation of the C—C bond lengths around the picrate aromatic ring in (I) are normal and can be related to the contributions of various resonance forms involving the nitro groups (Herbstein & Kaftory, 976). The N11/O12/O13 nitro group in (I) is twisted from the benzene ring plane by 46.55 (12)°, whereas the other two nitro groups are close to co-planar with the ring [equivalent dihedral angles for N12/O14/O15 and N13/O16/O17 = 3.03 (11) and 12.2 (2)°, respectively].

The two constituents of (I) interact by a strong, near linear N4—H4N···O11 link (Table 1). Then, centrosymmetric associtions of these ion pairs arise from the N3—HN3···O1ⁱ (see Table 1 for symmetry code) bond (Fig. 2). Two short intermolecular C—H···O interactions also occur (Table 1) and a short π-π stacking interaction involving the C1—C5/N1 ring and its inversion-generated partner at (1 - x, 2 - y, -z) with a centroid···centroid separation of 3.5486 (9) Å completes the structure of (I).

Related literature top

For the structure of nevirapine, see: Mui et al. (1992). For related structures, see: Harrison, Ashok et al. (2007); Harrison, Bindya et al. (2007). For background, see: Herbstein & Kaftory (1976); Bartlett (2005); Gazzard (2005); Manosuthi et al. (2007).

Experimental top

Nevirapine (2.66 g, 0.01 mol) was dissolved in 25 ml of ethanol. Picric acid (2.29 g, 0.01 mol) was dissolved in 10 ml of water. The solutions were mixed and 5 ml of 5M HCl was added to this mixture and stirred for few minutes. The resulting solid was filtered, dried and yellow crystals of (I) were obtained by slow evaporation of an ethanol solution (m.p.: 489–491 K; analysis for C₂₁H₁₇N₇O₈: Found (calculated): C 50.88 (50.91); H 3.39 (3.46); N 19.71% (19.79%).

Structure description top

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top

	Fig. 1. View of the molecular structure of (I) showing 50% displacement ellipsoids (arbitrary spheres for the H atoms). The hydrogen bond is shown as a double-dashed line.
	Fig. 2. View of a dimeric association of ion pairs in (I) with all C-bound H atoms omitted for clarity. Symmetry code as in Table 1.

Nevirapininium picrate top

Crystal data top

C₁₅H₁₅N₄O⁺·C₆H₂N₃O₇⁻	Z = 2
M_r = 495.42	F(000) = 512
Triclinic, P1	D_x = 1.515 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.9921 (5) Å	Cell parameters from 3856 reflections
b = 10.2126 (5) Å	θ = 2.3–27.5°
c = 11.5332 (6) Å	µ = 0.12 mm⁻¹
α = 70.716 (1)°	T = 291 K
β = 77.980 (1)°	Block, yellow
γ = 87.355 (1)°	0.40 × 0.30 × 0.24 mm
V = 1086.19 (9) Å³

Data collection top

Bruker SMART 1000 CCD diffractometer	4911 independent reflections
Radiation source: fine-focus sealed tube	3575 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.015
ω scans	θ_max = 27.5°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −12→12
T_min = 0.955, T_max = 0.972	k = −13→13
8228 measured reflections	l = −14→14

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.042	Hydrogen site location: difmap (N-H) and geom (C-H)
wR(F²) = 0.120	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0639P)² + 0.0965P] where P = (F_o² + 2F_c²)/3
4911 reflections	(Δ/σ)_max < 0.001
333 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₁₅H₁₅N₄O⁺·C₆H₂N₃O₇⁻	γ = 87.355 (1)°
M_r = 495.42	V = 1086.19 (9) Å³
Triclinic, P1	Z = 2
a = 9.9921 (5) Å	Mo Kα radiation
b = 10.2126 (5) Å	µ = 0.12 mm⁻¹
c = 11.5332 (6) Å	T = 291 K
α = 70.716 (1)°	0.40 × 0.30 × 0.24 mm
β = 77.980 (1)°

Data collection top

Bruker SMART 1000 CCD diffractometer	4911 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1999)	3575 reflections with I > 2σ(I)
T_min = 0.955, T_max = 0.972	R_int = 0.015
8228 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.120	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.25 e Å⁻³
4911 reflections	Δρ_min = −0.21 e Å⁻³
333 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.

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 > σ(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
C1	0.30569 (18)	1.05420 (17)	0.08754 (17)	0.0448 (4)
H1	0.2861	1.1430	0.0909	0.054*
C2	0.30848 (17)	1.03144 (17)	−0.02357 (16)	0.0426 (4)
H2	0.2879	1.1015	−0.0925	0.051*
C3	0.34278 (16)	0.90120 (16)	−0.02970 (15)	0.0373 (4)
H3	0.3497	0.8833	−0.1047	0.045*
C4	0.36700 (14)	0.79642 (14)	0.07669 (13)	0.0300 (3)
C5	0.35655 (14)	0.83030 (14)	0.18620 (14)	0.0306 (3)
C6	0.41730 (15)	0.66361 (15)	0.05906 (14)	0.0329 (3)
C7	0.31537 (15)	0.51453 (14)	0.27735 (13)	0.0310 (3)
C8	0.30914 (15)	0.60597 (15)	0.34613 (13)	0.0313 (3)
C9	0.16245 (17)	0.44673 (17)	0.51808 (15)	0.0413 (4)
H9	0.1121	0.4249	0.5998	0.050*
C10	0.16491 (17)	0.35632 (16)	0.45418 (15)	0.0409 (4)
H10	0.1151	0.2730	0.4916	0.049*
C11	0.24218 (16)	0.38812 (15)	0.33232 (14)	0.0354 (3)
C12	0.2488 (2)	0.28451 (18)	0.26464 (17)	0.0516 (5)
H12A	0.2239	0.3280	0.1848	0.077*
H12B	0.1865	0.2082	0.3138	0.077*
H12C	0.3402	0.2510	0.2520	0.077*
C13	0.40744 (19)	0.79138 (17)	0.39300 (15)	0.0436 (4)
H13	0.3329	0.8414	0.4286	0.052*
C14	0.4982 (2)	0.7114 (2)	0.47783 (19)	0.0604 (5)
H14A	0.5339	0.6250	0.4675	0.072*
H14B	0.4787	0.7122	0.5636	0.072*
C15	0.5491 (2)	0.8434 (3)	0.3756 (2)	0.0744 (7)
H15A	0.5606	0.9242	0.3995	0.089*
H15B	0.6157	0.8370	0.3034	0.089*
N1	0.32925 (14)	0.95717 (13)	0.19133 (13)	0.0408 (3)
N2	0.38048 (13)	0.73279 (12)	0.30040 (11)	0.0342 (3)
N3	0.40003 (14)	0.54343 (13)	0.15722 (12)	0.0355 (3)
H3N	0.4310 (18)	0.4702 (19)	0.1367 (16)	0.043*
N4	0.23304 (13)	0.56827 (14)	0.46307 (12)	0.0362 (3)
H4N	0.2240 (18)	0.6221 (19)	0.5097 (17)	0.043*
O1	0.47388 (13)	0.66345 (12)	−0.04642 (10)	0.0478 (3)
C21	0.14876 (16)	0.71482 (16)	0.73045 (14)	0.0356 (3)
C22	0.09458 (16)	0.83633 (15)	0.76164 (14)	0.0354 (3)
C23	0.05246 (16)	0.84102 (16)	0.88013 (15)	0.0373 (4)
H23	0.0128	0.9201	0.8940	0.045*
C24	0.07029 (16)	0.72442 (16)	0.98010 (14)	0.0361 (3)
C25	0.13314 (16)	0.60842 (16)	0.95952 (15)	0.0356 (3)
H25	0.1474	0.5326	1.0271	0.043*
C26	0.17471 (15)	0.60485 (15)	0.83888 (15)	0.0346 (3)
N11	0.08437 (17)	0.96236 (14)	0.65664 (14)	0.0460 (4)
N12	0.02625 (15)	0.72525 (16)	1.10704 (14)	0.0450 (3)
N13	0.24590 (15)	0.48166 (14)	0.82482 (14)	0.0432 (3)
O11	0.16134 (14)	0.71111 (13)	0.62164 (11)	0.0528 (3)
O12	0.18419 (18)	0.99914 (15)	0.57137 (15)	0.0781 (5)
O13	−0.02037 (18)	1.02612 (18)	0.65992 (16)	0.0875 (6)
O14	0.04083 (15)	0.61899 (16)	1.19367 (11)	0.0602 (4)
O15	−0.02505 (17)	0.83064 (15)	1.12454 (13)	0.0670 (4)
O16	0.24491 (16)	0.38042 (13)	0.91924 (13)	0.0620 (4)
O17	0.30523 (17)	0.48267 (15)	0.72064 (13)	0.0704 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0555 (10)	0.0274 (8)	0.0513 (10)	0.0056 (7)	−0.0086 (8)	−0.0145 (7)
C2	0.0482 (9)	0.0314 (8)	0.0428 (9)	0.0041 (7)	−0.0092 (7)	−0.0057 (7)
C3	0.0422 (8)	0.0363 (8)	0.0331 (8)	−0.0014 (6)	−0.0067 (7)	−0.0114 (7)
C4	0.0326 (7)	0.0267 (7)	0.0297 (7)	−0.0021 (5)	−0.0026 (6)	−0.0100 (6)
C5	0.0312 (7)	0.0278 (7)	0.0327 (8)	−0.0010 (5)	−0.0037 (6)	−0.0112 (6)
C6	0.0379 (8)	0.0298 (7)	0.0309 (8)	0.0009 (6)	−0.0038 (6)	−0.0117 (6)
C7	0.0381 (8)	0.0268 (7)	0.0288 (7)	0.0045 (6)	−0.0078 (6)	−0.0098 (6)
C8	0.0363 (7)	0.0288 (7)	0.0294 (7)	0.0038 (6)	−0.0078 (6)	−0.0103 (6)
C9	0.0469 (9)	0.0410 (9)	0.0300 (8)	−0.0010 (7)	−0.0010 (7)	−0.0074 (7)
C10	0.0488 (9)	0.0312 (8)	0.0372 (9)	−0.0027 (7)	−0.0045 (7)	−0.0063 (7)
C11	0.0442 (8)	0.0278 (7)	0.0345 (8)	0.0023 (6)	−0.0101 (7)	−0.0094 (6)
C12	0.0739 (12)	0.0345 (9)	0.0462 (10)	−0.0101 (8)	−0.0026 (9)	−0.0174 (8)
C13	0.0577 (10)	0.0426 (9)	0.0363 (9)	−0.0056 (7)	−0.0103 (8)	−0.0192 (7)
C14	0.0669 (13)	0.0731 (14)	0.0477 (11)	−0.0071 (10)	−0.0223 (10)	−0.0210 (10)
C15	0.0817 (15)	0.0929 (17)	0.0526 (12)	−0.0393 (13)	−0.0131 (11)	−0.0242 (12)
N1	0.0524 (8)	0.0301 (7)	0.0415 (8)	0.0026 (6)	−0.0071 (6)	−0.0154 (6)
N2	0.0445 (7)	0.0297 (6)	0.0304 (7)	−0.0012 (5)	−0.0082 (5)	−0.0121 (5)
N3	0.0476 (7)	0.0256 (6)	0.0321 (7)	0.0034 (5)	−0.0009 (6)	−0.0127 (5)
N4	0.0456 (7)	0.0342 (7)	0.0297 (7)	0.0019 (6)	−0.0036 (6)	−0.0142 (6)
O1	0.0695 (8)	0.0366 (6)	0.0324 (6)	0.0056 (5)	0.0036 (6)	−0.0139 (5)
C21	0.0413 (8)	0.0334 (8)	0.0318 (8)	0.0001 (6)	−0.0045 (6)	−0.0122 (6)
C22	0.0437 (8)	0.0275 (7)	0.0341 (8)	−0.0004 (6)	−0.0097 (7)	−0.0078 (6)
C23	0.0430 (8)	0.0322 (8)	0.0405 (9)	0.0028 (6)	−0.0090 (7)	−0.0169 (7)
C24	0.0402 (8)	0.0380 (8)	0.0313 (8)	−0.0019 (6)	−0.0060 (6)	−0.0134 (7)
C25	0.0395 (8)	0.0335 (8)	0.0323 (8)	−0.0013 (6)	−0.0091 (6)	−0.0077 (6)
C26	0.0391 (8)	0.0296 (7)	0.0354 (8)	0.0020 (6)	−0.0074 (6)	−0.0114 (6)
N11	0.0612 (9)	0.0333 (7)	0.0423 (8)	0.0015 (7)	−0.0130 (7)	−0.0095 (6)
N12	0.0475 (8)	0.0534 (9)	0.0376 (8)	0.0016 (7)	−0.0078 (6)	−0.0203 (7)
N13	0.0508 (8)	0.0354 (7)	0.0445 (8)	0.0080 (6)	−0.0110 (7)	−0.0148 (6)
O11	0.0816 (9)	0.0462 (7)	0.0326 (6)	0.0143 (6)	−0.0118 (6)	−0.0172 (5)
O12	0.0899 (11)	0.0531 (9)	0.0639 (10)	−0.0085 (8)	0.0036 (8)	0.0066 (7)
O13	0.0858 (12)	0.0721 (11)	0.0801 (12)	0.0331 (9)	−0.0187 (9)	0.0045 (9)
O14	0.0723 (9)	0.0698 (9)	0.0320 (7)	0.0122 (7)	−0.0091 (6)	−0.0107 (6)
O15	0.0913 (11)	0.0638 (9)	0.0536 (8)	0.0143 (8)	−0.0067 (8)	−0.0359 (7)
O16	0.0835 (10)	0.0364 (7)	0.0571 (8)	0.0168 (6)	−0.0146 (7)	−0.0054 (6)
O17	0.0959 (11)	0.0658 (9)	0.0487 (8)	0.0363 (8)	−0.0084 (8)	−0.0262 (7)

Geometric parameters (Å, º) top

C1—N1	1.335 (2)	C13—C15	1.486 (3)
C1—C2	1.370 (2)	C13—C14	1.490 (3)
C1—H1	0.9300	C13—H13	0.9800
C2—C3	1.379 (2)	C14—C15	1.493 (3)
C2—H2	0.9300	C14—H14A	0.9700
C3—C4	1.393 (2)	C14—H14B	0.9700
C3—H3	0.9300	C15—H15A	0.9700
C4—C5	1.399 (2)	C15—H15B	0.9700
C4—C6	1.4867 (19)	N3—H3N	0.881 (19)
C5—N1	1.3296 (18)	N4—H4N	0.878 (19)
C5—N2	1.4236 (19)	C21—O11	1.2480 (18)
C6—O1	1.2305 (17)	C21—C26	1.440 (2)
C6—N3	1.3559 (19)	C21—C22	1.454 (2)
C7—C11	1.399 (2)	C22—C23	1.360 (2)
C7—C8	1.4030 (19)	C22—N11	1.464 (2)
C7—N3	1.4097 (18)	C23—C24	1.392 (2)
C8—N4	1.3425 (19)	C23—H23	0.9300
C8—N2	1.3933 (18)	C24—C25	1.382 (2)
C9—N4	1.347 (2)	C24—N12	1.441 (2)
C9—C10	1.355 (2)	C25—C26	1.379 (2)
C9—H9	0.9300	C25—H25	0.9300
C10—C11	1.395 (2)	C26—N13	1.4557 (19)
C10—H10	0.9300	N11—O13	1.207 (2)
C11—C12	1.500 (2)	N11—O12	1.219 (2)
C12—H12A	0.9600	N12—O15	1.2294 (19)
C12—H12B	0.9600	N12—O14	1.2357 (19)
C12—H12C	0.9600	N13—O17	1.2211 (18)
C13—N2	1.4587 (19)	N13—O16	1.2278 (18)

N1—C1—C2	124.23 (14)	C15—C14—H14A	117.8
N1—C1—H1	117.9	C13—C14—H14B	117.8
C2—C1—H1	117.9	C15—C14—H14B	117.8
C1—C2—C3	117.77 (16)	H14A—C14—H14B	114.9
C1—C2—H2	121.1	C13—C15—C14	60.03 (13)
C3—C2—H2	121.1	C13—C15—H15A	117.8
C2—C3—C4	119.89 (15)	C14—C15—H15A	117.8
C2—C3—H3	120.1	C13—C15—H15B	117.8
C4—C3—H3	120.1	C14—C15—H15B	117.8
C3—C4—C5	117.31 (13)	H15A—C15—H15B	114.9
C3—C4—C6	116.49 (13)	C5—N1—C1	117.62 (14)
C5—C4—C6	125.80 (14)	C8—N2—C5	117.84 (12)
N1—C5—C4	123.08 (14)	C8—N2—C13	116.95 (12)
N1—C5—N2	114.28 (13)	C5—N2—C13	115.85 (12)
C4—C5—N2	122.58 (12)	C6—N3—C7	129.12 (13)
O1—C6—N3	120.04 (13)	C6—N3—H3N	113.9 (11)
O1—C6—C4	119.18 (13)	C7—N3—H3N	115.4 (11)
N3—C6—C4	120.77 (13)	C8—N4—C9	123.33 (13)
C11—C7—C8	119.18 (13)	C8—N4—H4N	122.4 (12)
C11—C7—N3	119.24 (12)	C9—N4—H4N	114.3 (12)
C8—C7—N3	121.48 (13)	O11—C21—C26	127.20 (14)
N4—C8—N2	118.15 (12)	O11—C21—C22	120.70 (15)
N4—C8—C7	118.47 (13)	C26—C21—C22	111.99 (13)
N2—C8—C7	123.36 (13)	C23—C22—C21	125.00 (14)
N4—C9—C10	119.90 (14)	C23—C22—N11	118.07 (14)
N4—C9—H9	120.1	C21—C22—N11	116.93 (13)
C10—C9—H9	120.1	C22—C23—C24	118.30 (14)
C9—C10—C11	120.04 (14)	C22—C23—H23	120.9
C9—C10—H10	120.0	C24—C23—H23	120.9
C11—C10—H10	120.0	C25—C24—C23	120.94 (14)
C10—C11—C7	119.08 (14)	C25—C24—N12	119.15 (15)
C10—C11—C12	119.49 (14)	C23—C24—N12	119.89 (14)
C7—C11—C12	121.41 (14)	C26—C25—C24	120.10 (15)
C11—C12—H12A	109.5	C26—C25—H25	120.0
C11—C12—H12B	109.5	C24—C25—H25	120.0
H12A—C12—H12B	109.5	C25—C26—C21	122.93 (14)
C11—C12—H12C	109.5	C25—C26—N13	116.69 (14)
H12A—C12—H12C	109.5	C21—C26—N13	120.37 (13)
H12B—C12—H12C	109.5	O13—N11—O12	123.37 (17)
N2—C13—C15	116.94 (15)	O13—N11—C22	118.84 (15)
N2—C13—C14	116.71 (15)	O12—N11—C22	117.77 (16)
C15—C13—C14	60.23 (14)	O15—N12—O14	122.93 (15)
N2—C13—H13	117.0	O15—N12—C24	118.83 (15)
C15—C13—H13	117.0	O14—N12—C24	118.24 (14)
C14—C13—H13	117.0	O17—N13—O16	122.36 (14)
C13—C14—C15	59.74 (14)	O17—N13—C26	119.31 (14)
C13—C14—H14A	117.8	O16—N13—C26	118.33 (14)

N1—C1—C2—C3	−2.5 (3)	C15—C13—N2—C5	−81.3 (2)
C1—C2—C3—C4	2.9 (2)	C14—C13—N2—C5	−149.74 (15)
C2—C3—C4—C5	−0.8 (2)	O1—C6—N3—C7	−165.46 (15)
C2—C3—C4—C6	−173.88 (14)	C4—C6—N3—C7	13.8 (2)
C3—C4—C5—N1	−2.2 (2)	C11—C7—N3—C6	138.44 (16)
C6—C4—C5—N1	170.24 (14)	C8—C7—N3—C6	−45.4 (2)
C3—C4—C5—N2	−179.24 (13)	N2—C8—N4—C9	−178.36 (15)
C6—C4—C5—N2	−6.8 (2)	C7—C8—N4—C9	0.2 (2)
C3—C4—C6—O1	22.0 (2)	C10—C9—N4—C8	−0.8 (3)
C5—C4—C6—O1	−150.49 (15)	O11—C21—C22—C23	166.67 (16)
C3—C4—C6—N3	−157.26 (14)	C26—C21—C22—C23	−9.7 (2)
C5—C4—C6—N3	30.3 (2)	O11—C21—C22—N11	−13.0 (2)
C11—C7—C8—N4	0.2 (2)	C26—C21—C22—N11	170.67 (13)
N3—C7—C8—N4	−175.92 (14)	C21—C22—C23—C24	4.5 (2)
C11—C7—C8—N2	178.69 (14)	N11—C22—C23—C24	−175.84 (14)
N3—C7—C8—N2	2.5 (2)	C22—C23—C24—C25	2.1 (2)
N4—C9—C10—C11	1.0 (3)	C22—C23—C24—N12	−179.67 (14)
C9—C10—C11—C7	−0.6 (3)	C23—C24—C25—C26	−2.4 (2)
C9—C10—C11—C12	177.43 (17)	N12—C24—C25—C26	179.29 (14)
C8—C7—C11—C10	0.0 (2)	C24—C25—C26—C21	−3.8 (2)
N3—C7—C11—C10	176.22 (15)	C24—C25—C26—N13	177.17 (13)
C8—C7—C11—C12	−178.01 (16)	O11—C21—C26—C25	−166.96 (16)
N3—C7—C11—C12	−1.8 (2)	C22—C21—C26—C25	9.1 (2)
N2—C13—C14—C15	107.25 (18)	O11—C21—C26—N13	12.1 (3)
N2—C13—C15—C14	−106.86 (18)	C22—C21—C26—N13	−171.83 (13)
C4—C5—N1—C1	2.7 (2)	C23—C22—N11—O13	−46.4 (2)
N2—C5—N1—C1	180.00 (14)	C21—C22—N11—O13	133.22 (18)
C2—C1—N1—C5	−0.3 (3)	C23—C22—N11—O12	131.86 (18)
N4—C8—N2—C5	−124.09 (15)	C21—C22—N11—O12	−48.5 (2)
C7—C8—N2—C5	57.4 (2)	C25—C24—N12—O15	177.36 (15)
N4—C8—N2—C13	21.2 (2)	C23—C24—N12—O15	−0.9 (2)
C7—C8—N2—C13	−157.30 (15)	C25—C24—N12—O14	−3.3 (2)
N1—C5—N2—C8	130.07 (13)	C23—C24—N12—O14	178.44 (15)
C4—C5—N2—C8	−52.61 (19)	C25—C26—N13—O17	−167.53 (16)
N1—C5—N2—C13	−15.56 (19)	C21—C26—N13—O17	13.4 (2)
C4—C5—N2—C13	161.75 (14)	C25—C26—N13—O16	11.8 (2)
C15—C13—N2—C8	132.73 (18)	C21—C26—N13—O16	−167.29 (15)
C14—C13—N2—C8	64.3 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N···O1ⁱ	0.881 (19)	2.063 (19)	2.9242 (17)	165.4 (16)
N4—H4N···O11	0.878 (19)	1.808 (19)	2.6656 (17)	164.9 (17)
C9—H9···O14ⁱⁱ	0.93	2.46	3.386 (2)	174
C23—H23···O15ⁱⁱⁱ	0.93	2.49	3.335 (2)	151

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₅N₄O⁺·C₆H₂N₃O₇⁻
M_r	495.42
Crystal system, space group	Triclinic, P1
Temperature (K)	291
a, b, c (Å)	9.9921 (5), 10.2126 (5), 11.5332 (6)
α, β, γ (°)	70.716 (1), 77.980 (1), 87.355 (1)
V (Å³)	1086.19 (9)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.40 × 0.30 × 0.24

Data collection
Diffractometer	Bruker SMART 1000 CCD
Absorption correction	Multi-scan (SADABS; Bruker, 1999)
T_min, T_max	0.955, 0.972
No. of measured, independent and observed [I > 2σ(I)] reflections	8228, 4911, 3575
R_int	0.015
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.120, 1.05
No. of reflections	4911
No. of parameters	333
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.21

Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N···O1ⁱ	0.881 (19)	2.063 (19)	2.9242 (17)	165.4 (16)
N4—H4N···O11	0.878 (19)	1.808 (19)	2.6656 (17)	164.9 (17)
C9—H9···O14ⁱⁱ	0.93	2.46	3.386 (2)	174
C23—H23···O15ⁱⁱⁱ	0.93	2.49	3.335 (2)	151

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

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