1-Piperonylpiperazinium picrate.

IN THE CATION OF THE TITLE SALT [SYSTEMATIC NAME: 4-(2H-1,3-benzodioxol-5-ylmeth-yl)piperazin-1-ium 2,4,6-tri-nitro-phen-o-late], C12H17N2O2 (+)·C6H2N3O7 (-), the piperazine ring adopts a slightly disordered chair conformation. The piperonyl ring system and the piperazine ring are twisted with respect to each other with an N-C-C-C torsion angle of 40.7 (2)°. In the anion, the dihedral angles between the mean planes of the nitro substituents ortho to the phenolate O atom and the mean plane of the phenyl ring are 28.8 (9) and 32.2 (8)°. In contrast, the nitro group in the para position lies much closer to the aromatic ring plane, subtending a dihedral angle of 3.0 (1)°. In the crystal, the cations and anions inter-act through N-H⋯O hydrogen bonds and a weak C-H⋯O inter-action. Weak C-H⋯O inter-actions are also observed between the anions, forming R 2 (2)(10) graph-set ring motifs. In addition, a weak centroid-centroid π-π stacking inter-action between the aromatic rings of the cation and the anion, with an inter-centroid distance of 3.7471 (9) Å, contributes to the crystal packing, resulting in a two-dimensional network along (10-1).

Related literature

For pharmaceutical applications of the title cation, see: Millan et al. (2001 ▶) and for the pharmacological and toxicological uses of piperazine derivatives, see: Brockunier et al. (2004 ▶); Bogatcheva et al. (2006 ▶); Choudhary et al. (2006 ▶); Elliott (2011 ▶); Kharb et al. (2012 ▶). For a related structure, see: Capuano et al. (2000 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶) and for standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C12H17N2O2 +·C6H2N3O7 −

M = 449.38

Monoclinic,

a = 12.0864 (2) Å

b = 6.96981 (11) Å

c = 23.4898 (4) Å

β = 96.5141 (17)°

V = 1965.99 (6) Å3

Z = 4

Cu Kα radiation

μ = 1.06 mm−1

T = 173 K

0.48 × 0.24 × 0.22 mm

Data collection

Agilent Gemini EOS diffractometer

Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012 ▶) T min = 0.761, T max = 1.000

12154 measured reflections

3837 independent reflections

3316 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.121

S = 1.05

3837 reflections

298 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.29 e Å−3

Δρmin = −0.21 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012 ▶); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007 ▶); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814001524/sj5385sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814001524/sj5385Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814001524/sj5385Isup3.cml

CCDC reference:

Additional supporting information: crystallographic information; 3D view; checkCIF report

C12H17N2O2+·C6H2N3O7−	F(000) = 936
Mr = 449.38	Dx = 1.518 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.5418 Å
a = 12.0864 (2) Å	Cell parameters from 4971 reflections
b = 6.96981 (11) Å	θ = 3.7–72.4°
c = 23.4898 (4) Å	µ = 1.06 mm−1
β = 96.5141 (17)°	T = 173 K
V = 1965.99 (6) Å3	Irregular, dark yellow
Z = 4	0.48 × 0.24 × 0.22 mm

Agilent Gemini EOS diffractometer	3837 independent reflections
Radiation source: Enhance (Cu) X-ray Source	3316 reflections with I > 2σ(I)
Detector resolution: 16.0416 pixels mm-1	Rint = 0.033
ω scans	θmax = 72.5°, θmin = 3.8°
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012)	h = −13→14
Tmin = 0.761, Tmax = 1.000	k = −6→8
12154 measured reflections	l = −28→28

Refinement on F2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.043	w = 1/[σ2(Fo2) + (0.0679P)2 + 0.5476P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.121	(Δ/σ)max < 0.001
S = 1.05	Δρmax = 0.29 e Å−3
3837 reflections	Δρmin = −0.21 e Å−3
298 parameters	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraints	Extinction coefficient: 0.0016 (2)
Primary atom site location: structure-invariant direct methods

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

	x	y	z	Uiso*/Ueq
O1B	0.84597 (9)	0.58513 (17)	0.47124 (5)	0.0352 (3)
O2B	0.77598 (13)	0.8599 (2)	0.53866 (6)	0.0578 (4)
O3B	0.64101 (13)	1.01645 (19)	0.49224 (7)	0.0570 (4)
O4B	0.32910 (10)	0.61289 (19)	0.42367 (6)	0.0463 (3)
O5B	0.35919 (10)	0.34651 (18)	0.38117 (6)	0.0461 (3)
O6B	0.73947 (12)	0.1561 (2)	0.36561 (7)	0.0598 (4)
O7B	0.85686 (11)	0.2174 (2)	0.43946 (7)	0.0571 (4)
N1B	0.69547 (12)	0.8710 (2)	0.50202 (6)	0.0372 (3)
N2B	0.39201 (11)	0.4894 (2)	0.40823 (6)	0.0331 (3)
N3B	0.76868 (11)	0.2469 (2)	0.40934 (6)	0.0372 (3)
C1B	0.74326 (12)	0.5605 (2)	0.45716 (6)	0.0274 (3)
C2B	0.66022 (13)	0.6984 (2)	0.46929 (6)	0.0285 (3)
C3B	0.54835 (13)	0.6790 (2)	0.45310 (6)	0.0286 (3)
H3B	0.4975	0.7755	0.4621	0.034*
C4B	0.51081 (12)	0.5151 (2)	0.42331 (6)	0.0277 (3)
C5B	0.58320 (13)	0.3750 (2)	0.40867 (6)	0.0283 (3)
H5B	0.5563	0.2651	0.3875	0.034*
C6B	0.69516 (12)	0.3982 (2)	0.42543 (6)	0.0288 (3)
O1A	0.46181 (10)	0.97115 (18)	0.33755 (6)	0.0418 (3)
O2A	0.31610 (10)	0.78306 (19)	0.29640 (6)	0.0478 (3)
N1A	0.49795 (10)	0.22233 (18)	0.18479 (5)	0.0281 (3)
N2A	0.45154 (12)	0.0793 (2)	0.07075 (6)	0.0403 (4)
C1A	0.57171 (13)	0.2789 (2)	0.23569 (7)	0.0335 (4)
H1AA	0.6493	0.2816	0.2260	0.040*
H1AB	0.5676	0.1805	0.2658	0.040*
C2A	0.54431 (13)	0.4722 (2)	0.25959 (6)	0.0293 (3)
C3A	0.63089 (12)	0.5898 (2)	0.28273 (7)	0.0314 (3)
H3A	0.7054	0.5514	0.2798	0.038*
C4A	0.61191 (13)	0.7628 (2)	0.31028 (7)	0.0320 (3)
H4A	0.6714	0.8418	0.3265	0.038*
C5A	0.50268 (13)	0.8118 (2)	0.31260 (6)	0.0303 (3)
C6A	0.34372 (15)	0.9629 (3)	0.32388 (9)	0.0469 (5)
H6AA	0.3181	1.0701	0.2980	0.056*
H6AB	0.3068	0.9741	0.3592	0.056*
C7A	0.41608 (13)	0.6991 (2)	0.28819 (7)	0.0320 (3)
C8A	0.43308 (13)	0.5274 (2)	0.26208 (7)	0.0316 (3)
H8A	0.3727	0.4495	0.2464	0.038*
C9A	0.51724 (14)	0.0216 (2)	0.17120 (7)	0.0342 (4)
H9AA	0.5076	−0.0591	0.2050	0.041*
H9AB	0.5947	0.0056	0.1621	0.041*
C10A	0.43710 (14)	−0.0439 (3)	0.12078 (8)	0.0403 (4)
H10A	0.4521	−0.1794	0.1117	0.048*
H10B	0.3596	−0.0343	0.1303	0.048*
C11A	0.43605 (16)	0.2859 (3)	0.08385 (8)	0.0441 (4)
H11A	0.3584	0.3089	0.0917	0.053*
H11B	0.4505	0.3653	0.0505	0.053*
C12A	0.51592 (14)	0.3411 (2)	0.13567 (7)	0.0356 (4)
H12A	0.5935	0.3251	0.1268	0.043*
H12B	0.5049	0.4777	0.1451	0.043*
H2AA	0.522 (2)	0.062 (3)	0.0623 (9)	0.053 (6)*
H2AB	0.403 (2)	0.044 (3)	0.0403 (10)	0.056 (6)*

	U11	U22	U33	U12	U13	U23
O1B	0.0238 (6)	0.0469 (7)	0.0338 (6)	−0.0022 (5)	−0.0014 (4)	0.0020 (5)
O2B	0.0567 (9)	0.0563 (9)	0.0564 (9)	−0.0110 (7)	−0.0116 (7)	−0.0159 (7)
O3B	0.0560 (9)	0.0345 (7)	0.0808 (11)	0.0035 (6)	0.0096 (7)	−0.0108 (7)
O4B	0.0263 (6)	0.0505 (8)	0.0615 (8)	0.0095 (5)	0.0023 (5)	−0.0064 (6)
O5B	0.0281 (6)	0.0474 (7)	0.0620 (8)	−0.0078 (5)	0.0014 (5)	−0.0133 (6)
O6B	0.0429 (8)	0.0581 (9)	0.0773 (10)	0.0081 (6)	0.0021 (7)	−0.0352 (8)
O7B	0.0349 (7)	0.0571 (9)	0.0762 (10)	0.0191 (6)	−0.0069 (7)	−0.0085 (7)
N1B	0.0373 (8)	0.0353 (8)	0.0397 (8)	−0.0064 (6)	0.0069 (6)	−0.0046 (6)
N2B	0.0244 (7)	0.0388 (7)	0.0360 (7)	0.0011 (5)	0.0027 (5)	0.0025 (6)
N3B	0.0278 (7)	0.0346 (7)	0.0495 (9)	0.0025 (6)	0.0055 (6)	−0.0040 (6)
C1B	0.0243 (7)	0.0346 (8)	0.0227 (7)	0.0000 (6)	0.0007 (5)	0.0048 (6)
C2B	0.0294 (8)	0.0300 (8)	0.0257 (7)	−0.0016 (6)	0.0021 (6)	0.0011 (6)
C3B	0.0276 (8)	0.0313 (7)	0.0273 (7)	0.0038 (6)	0.0051 (6)	0.0033 (6)
C4B	0.0228 (7)	0.0342 (8)	0.0259 (7)	0.0007 (6)	0.0015 (6)	0.0033 (6)
C5B	0.0275 (8)	0.0303 (7)	0.0269 (7)	−0.0010 (6)	0.0023 (6)	−0.0003 (6)
C6B	0.0258 (8)	0.0304 (8)	0.0304 (7)	0.0036 (6)	0.0035 (6)	0.0015 (6)
O1A	0.0320 (6)	0.0398 (7)	0.0528 (8)	0.0017 (5)	0.0007 (5)	−0.0153 (5)
O2A	0.0259 (6)	0.0481 (7)	0.0684 (9)	0.0020 (5)	0.0013 (6)	−0.0207 (6)
N1A	0.0256 (6)	0.0306 (6)	0.0271 (6)	−0.0010 (5)	−0.0008 (5)	−0.0014 (5)
N2A	0.0240 (7)	0.0642 (10)	0.0313 (7)	0.0038 (6)	−0.0036 (6)	−0.0126 (7)
C1A	0.0297 (8)	0.0351 (8)	0.0336 (8)	0.0028 (6)	−0.0054 (6)	−0.0029 (6)
C2A	0.0270 (8)	0.0328 (8)	0.0269 (7)	−0.0014 (6)	−0.0015 (6)	0.0004 (6)
C3A	0.0222 (7)	0.0366 (8)	0.0350 (8)	−0.0011 (6)	0.0006 (6)	0.0003 (6)
C4A	0.0251 (8)	0.0361 (8)	0.0334 (8)	−0.0062 (6)	−0.0019 (6)	−0.0013 (6)
C5A	0.0323 (8)	0.0306 (8)	0.0277 (7)	−0.0021 (6)	0.0015 (6)	−0.0017 (6)
C6A	0.0312 (9)	0.0449 (10)	0.0639 (12)	0.0027 (7)	0.0025 (8)	−0.0148 (9)
C7A	0.0228 (7)	0.0391 (8)	0.0335 (8)	−0.0006 (6)	0.0004 (6)	−0.0003 (6)
C8A	0.0244 (7)	0.0355 (8)	0.0333 (8)	−0.0043 (6)	−0.0032 (6)	−0.0040 (6)
C9A	0.0347 (8)	0.0313 (8)	0.0353 (8)	0.0012 (6)	−0.0018 (7)	−0.0021 (6)
C10A	0.0316 (9)	0.0432 (9)	0.0451 (10)	−0.0040 (7)	−0.0001 (7)	−0.0112 (8)
C11A	0.0422 (10)	0.0556 (11)	0.0332 (9)	0.0114 (8)	−0.0009 (7)	0.0044 (8)
C12A	0.0379 (9)	0.0355 (8)	0.0330 (8)	0.0006 (7)	0.0029 (7)	0.0023 (6)

O1B—C1B	1.2597 (18)	N2A—H2AA	0.91 (2)
O2B—N1B	1.226 (2)	N2A—H2AB	0.91 (2)
O3B—N1B	1.216 (2)	C1A—H1AA	0.9900
O4B—N2B	1.2298 (18)	C1A—H1AB	0.9900
O5B—N2B	1.2234 (18)	C1A—C2A	1.511 (2)
O6B—N3B	1.2240 (19)	C2A—C3A	1.390 (2)
O7B—N3B	1.2278 (18)	C2A—C8A	1.406 (2)
N1B—C2B	1.465 (2)	C3A—H3A	0.9500
N2B—C4B	1.4505 (19)	C3A—C4A	1.400 (2)
N3B—C6B	1.456 (2)	C4A—H4A	0.9500
C1B—C2B	1.441 (2)	C4A—C5A	1.371 (2)
C1B—C6B	1.441 (2)	C5A—C7A	1.380 (2)
C2B—C3B	1.369 (2)	C6A—H6AA	0.9900
C3B—H3B	0.9500	C6A—H6AB	0.9900
C3B—C4B	1.388 (2)	C7A—C8A	1.371 (2)
C4B—C5B	1.381 (2)	C8A—H8A	0.9500
C5B—H5B	0.9500	C9A—H9AA	0.9900
C5B—C6B	1.375 (2)	C9A—H9AB	0.9900
O1A—C5A	1.3735 (19)	C9A—C10A	1.513 (2)
O1A—C6A	1.428 (2)	C10A—H10A	0.9900
O2A—C6A	1.432 (2)	C10A—H10B	0.9900
O2A—C7A	1.3757 (19)	C11A—H11A	0.9900
N1A—C1A	1.4621 (19)	C11A—H11B	0.9900
N1A—C9A	1.460 (2)	C11A—C12A	1.515 (2)
N1A—C12A	1.456 (2)	C12A—H12A	0.9900
N2A—C10A	1.481 (2)	C12A—H12B	0.9900
N2A—C11A	1.489 (2)
O2B—N1B—C2B	118.49 (14)	C8A—C2A—C1A	120.69 (14)
O3B—N1B—O2B	123.68 (15)	C2A—C3A—H3A	118.9
O3B—N1B—C2B	117.80 (14)	C2A—C3A—C4A	122.20 (14)
O4B—N2B—C4B	118.01 (14)	C4A—C3A—H3A	118.9
O5B—N2B—O4B	123.24 (14)	C3A—C4A—H4A	121.9
O5B—N2B—C4B	118.76 (13)	C5A—C4A—C3A	116.24 (14)
O6B—N3B—O7B	123.10 (15)	C5A—C4A—H4A	121.9
O6B—N3B—C6B	117.76 (14)	O1A—C5A—C7A	110.17 (14)
O7B—N3B—C6B	119.13 (14)	C4A—C5A—O1A	127.81 (14)
O1B—C1B—C2B	123.00 (14)	C4A—C5A—C7A	122.01 (15)
O1B—C1B—C6B	124.81 (14)	O1A—C6A—O2A	108.21 (13)
C6B—C1B—C2B	112.14 (13)	O1A—C6A—H6AA	110.1
C1B—C2B—N1B	118.95 (13)	O1A—C6A—H6AB	110.1
C3B—C2B—N1B	116.50 (13)	O2A—C6A—H6AA	110.1
C3B—C2B—C1B	124.54 (14)	O2A—C6A—H6AB	110.1
C2B—C3B—H3B	120.7	H6AA—C6A—H6AB	108.4
C2B—C3B—C4B	118.51 (14)	O2A—C7A—C5A	109.66 (14)
C4B—C3B—H3B	120.7	C8A—C7A—O2A	127.79 (14)
C3B—C4B—N2B	118.85 (13)	C8A—C7A—C5A	122.51 (15)
C5B—C4B—N2B	119.31 (14)	C2A—C8A—H8A	121.6
C5B—C4B—C3B	121.83 (14)	C7A—C8A—C2A	116.75 (14)
C4B—C5B—H5B	120.8	C7A—C8A—H8A	121.6
C6B—C5B—C4B	118.45 (14)	N1A—C9A—H9AA	109.5
C6B—C5B—H5B	120.8	N1A—C9A—H9AB	109.5
C1B—C6B—N3B	118.73 (13)	N1A—C9A—C10A	110.87 (13)
C5B—C6B—N3B	116.76 (13)	H9AA—C9A—H9AB	108.1
C5B—C6B—C1B	124.50 (14)	C10A—C9A—H9AA	109.5
C5A—O1A—C6A	105.68 (12)	C10A—C9A—H9AB	109.5
C7A—O2A—C6A	105.78 (12)	N2A—C10A—C9A	108.90 (14)
C9A—N1A—C1A	109.85 (12)	N2A—C10A—H10A	109.9
C12A—N1A—C1A	111.28 (13)	N2A—C10A—H10B	109.9
C12A—N1A—C9A	109.25 (12)	C9A—C10A—H10A	109.9
C10A—N2A—C11A	111.56 (14)	C9A—C10A—H10B	109.9
C10A—N2A—H2AA	107.4 (14)	H10A—C10A—H10B	108.3
C10A—N2A—H2AB	110.1 (15)	N2A—C11A—H11A	109.9
C11A—N2A—H2AA	108.3 (14)	N2A—C11A—H11B	109.9
C11A—N2A—H2AB	109.7 (15)	N2A—C11A—C12A	109.15 (14)
H2AA—N2A—H2AB	110 (2)	H11A—C11A—H11B	108.3
N1A—C1A—H1AA	108.8	C12A—C11A—H11A	109.9
N1A—C1A—H1AB	108.8	C12A—C11A—H11B	109.9
N1A—C1A—C2A	113.90 (13)	N1A—C12A—C11A	110.72 (14)
H1AA—C1A—H1AB	107.7	N1A—C12A—H12A	109.5
C2A—C1A—H1AA	108.8	N1A—C12A—H12B	109.5
C2A—C1A—H1AB	108.8	C11A—C12A—H12A	109.5
C3A—C2A—C1A	118.94 (14)	C11A—C12A—H12B	109.5
C3A—C2A—C8A	120.22 (15)	H12A—C12A—H12B	108.1
O1B—C1B—C2B—N1B	−3.2 (2)	O2A—C7A—C8A—C2A	−179.39 (16)
O1B—C1B—C2B—C3B	177.92 (14)	N1A—C1A—C2A—C3A	−143.67 (15)
O1B—C1B—C6B—N3B	1.8 (2)	N1A—C1A—C2A—C8A	40.7 (2)
O1B—C1B—C6B—C5B	−177.91 (14)	N1A—C9A—C10A—N2A	58.56 (18)
O2B—N1B—C2B—C1B	−32.4 (2)	N2A—C11A—C12A—N1A	−57.98 (19)
O2B—N1B—C2B—C3B	146.50 (16)	C1A—N1A—C9A—C10A	176.60 (14)
O3B—N1B—C2B—C1B	149.48 (15)	C1A—N1A—C12A—C11A	−177.88 (14)
O3B—N1B—C2B—C3B	−31.6 (2)	C1A—C2A—C3A—C4A	−174.11 (15)
O4B—N2B—C4B—C3B	−1.5 (2)	C1A—C2A—C8A—C7A	175.38 (14)
O4B—N2B—C4B—C5B	177.30 (14)	C2A—C3A—C4A—C5A	−0.8 (2)
O5B—N2B—C4B—C3B	178.82 (14)	C3A—C2A—C8A—C7A	−0.2 (2)
O5B—N2B—C4B—C5B	−2.4 (2)	C3A—C4A—C5A—O1A	179.11 (15)
O6B—N3B—C6B—C1B	−150.82 (16)	C3A—C4A—C5A—C7A	−1.2 (2)
O6B—N3B—C6B—C5B	28.9 (2)	C4A—C5A—C7A—O2A	−179.39 (15)
O7B—N3B—C6B—C1B	28.4 (2)	C4A—C5A—C7A—C8A	2.7 (3)
O7B—N3B—C6B—C5B	−151.86 (16)	C5A—O1A—C6A—O2A	7.0 (2)
N1B—C2B—C3B—C4B	−178.32 (13)	C5A—C7A—C8A—C2A	−1.8 (2)
N2B—C4B—C5B—C6B	−177.33 (13)	C6A—O1A—C5A—C4A	175.15 (17)
C1B—C2B—C3B—C4B	0.6 (2)	C6A—O1A—C5A—C7A	−4.53 (19)
C2B—C1B—C6B—N3B	179.38 (13)	C6A—O2A—C7A—C5A	4.0 (2)
C2B—C1B—C6B—C5B	−0.4 (2)	C6A—O2A—C7A—C8A	−178.15 (17)
C2B—C3B—C4B—N2B	177.29 (13)	C7A—O2A—C6A—O1A	−6.8 (2)
C2B—C3B—C4B—C5B	−1.5 (2)	C8A—C2A—C3A—C4A	1.6 (2)
C3B—C4B—C5B—C6B	1.4 (2)	C9A—N1A—C1A—C2A	−169.57 (13)
C4B—C5B—C6B—N3B	179.77 (13)	C9A—N1A—C12A—C11A	60.66 (17)
C4B—C5B—C6B—C1B	−0.5 (2)	C10A—N2A—C11A—C12A	56.16 (19)
C6B—C1B—C2B—N1B	179.19 (13)	C11A—N2A—C10A—C9A	−56.31 (18)
C6B—C1B—C2B—C3B	0.3 (2)	C12A—N1A—C1A—C2A	69.32 (17)
O1A—C5A—C7A—O2A	0.31 (19)	C12A—N1A—C9A—C10A	−61.07 (17)
O1A—C5A—C7A—C8A	−177.63 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N2A—H2AA···O1Bi	0.91 (2)	1.86 (3)	2.7409 (19)	163 (2)
N2A—H2AB···O1Bii	0.91 (2)	1.91 (2)	2.7798 (18)	159 (2)
C4A—H4A···O6Biii	0.95	2.48	3.335 (2)	150
C3B—H3B···O3Biv	0.95	2.54	3.473 (2)	166

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2A—H2AA⋯O1B i	0.91 (2)	1.86 (3)	2.7409 (19)	163 (2)
N2A—H2AB⋯O1B ii	0.91 (2)	1.91 (2)	2.7798 (18)	159 (2)
C4A—H4A⋯O6B iii	0.95	2.48	3.335 (2)	150
C3B—H3B⋯O3B iv	0.95	2.54	3.473 (2)	166

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .