4-(Furan-2-carbon-yl)piperazin-1-ium 3,5-di-nitro-benzoate.

In the cation of the title salt, C9H13N2O2 (+)·C7H3N2O6 (-), the piperazine ring adopts a slightly distorted chair conformation. Twofold rotational disorder is exhibited by the furan ring in a 0.430 (4):0.570 (4) ratio. In the crystal, N-H⋯O hydrogen bonds link the ions into chains along [010]. Additional weak C-H⋯O inter-actions are observed, leading to a supra-molecular layer parallel to (011).

Related literature

For the synthesis of the drug Prazosin {systematic name: 2-[4-(2-furo­yl)piperazin-1-yl]-6,7-di­meth­oxy­quinazolin-4-amine}, see: Honkanen et al. (1980 ▶). For the drug 1(2-furo­yl)piperazine, used in the treatment of high blood pressure and anxiety, see: Brogden et al. (1977 ▶). For therapeutic uses of piperazines, see: Brockunier et al. (2004 ▶); Bogatcheva et al. (2006 ▶). For the use of the piperazine moiety in the construction of bioactive mol­ecules, see: Choudhary et al. (2006 ▶). For a related structure, see: Dayananda et al. (2012 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C9H13N2O2 +·C7H3N2O6 −

M = 392.33

Orthorhombic,

a = 9.6060 (2) Å

b = 10.4572 (2) Å

c = 33.8766 (7) Å

V = 3402.97 (13) Å3

Z = 8

Cu Kα radiation

μ = 1.08 mm−1

T = 173 K

0.28 × 0.22 × 0.18 mm

Data collection

Agilent Eos Gemini diffractometer

Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012 ▶) T min = 0.863, T max = 1.000

21195 measured reflections

3352 independent reflections

2915 reflections with I > 2σ(I)

R int = 0.079

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.123

S = 1.02

3352 reflections

270 parameters

10 restraints

H-atom parameters constrained

Δρmax = 0.26 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/S160053681401126X/tk5314sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681401126X/tk5314Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S160053681401126X/tk5314Isup3.cml

CCDC reference: 1003444

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

C9H13N2O2+·C7H3N2O6−	Dx = 1.532 Mg m−3
Mr = 392.33	Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, Pbca	Cell parameters from 7148 reflections
a = 9.6060 (2) Å	θ = 3.9–72.3°
b = 10.4572 (2) Å	µ = 1.08 mm−1
c = 33.8766 (7) Å	T = 173 K
V = 3402.97 (13) Å3	Irregular, colourless
Z = 8	0.28 × 0.22 × 0.18 mm
F(000) = 1632

Agilent Eos Gemini diffractometer	2915 reflections with I > 2σ(I)
Detector resolution: 16.0416 pixels mm-1	Rint = 0.079
ω scans	θmax = 72.4°, θmin = 5.2°
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012)	h = −10→11
Tmin = 0.863, Tmax = 1.000	k = −12→12
21195 measured reflections	l = −30→41
3352 independent reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.043	w = 1/[σ2(Fo2) + (0.0723P)2 + 0.8847P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.123	(Δ/σ)max = 0.001
S = 1.02	Δρmax = 0.26 e Å−3
3352 reflections	Δρmin = −0.21 e Å−3
270 parameters	Extinction correction: SHELXL2012 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
10 restraints	Extinction coefficient: 0.0015 (3)
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	Occ. (<1)
O1A	0.36870 (12)	0.57178 (10)	0.63310 (3)	0.0284 (3)
O2A	0.28703 (12)	0.69735 (10)	0.68122 (3)	0.0317 (3)
O3A	0.42159 (14)	0.60237 (15)	0.81693 (3)	0.0463 (4)
O4A	0.58504 (14)	0.46802 (13)	0.82985 (3)	0.0415 (3)
O5A	0.82825 (13)	0.26144 (13)	0.72229 (4)	0.0456 (3)
O6A	0.77657 (15)	0.31036 (13)	0.66197 (4)	0.0468 (4)
N1A	0.51100 (13)	0.52552 (13)	0.80671 (4)	0.0281 (3)
N2A	0.75838 (14)	0.31806 (13)	0.69759 (4)	0.0326 (3)
C1A	0.36297 (15)	0.60956 (14)	0.66819 (4)	0.0239 (3)
C2A	0.45703 (14)	0.54250 (13)	0.69778 (4)	0.0224 (3)
C3A	0.44092 (15)	0.56475 (13)	0.73799 (4)	0.0223 (3)
H3A	0.3713	0.6217	0.7473	0.027*
C4A	0.52856 (15)	0.50207 (14)	0.76415 (4)	0.0233 (3)
C5A	0.63161 (15)	0.41803 (14)	0.75234 (4)	0.0252 (3)
H5A	0.6891	0.3744	0.7708	0.030*
C6A	0.64582 (15)	0.40151 (14)	0.71212 (4)	0.0254 (3)
C7A	0.56135 (15)	0.46153 (14)	0.68461 (4)	0.0241 (3)
H7A	0.5748	0.4474	0.6572	0.029*
O1B	0.49213 (15)	0.72567 (16)	0.51522 (4)	0.0557 (4)
O2B	0.6605 (4)	0.6627 (4)	0.57013 (17)	0.0347 (6)	0.430 (4)
C6B	0.672 (3)	0.602 (3)	0.5349 (8)	0.023 (2)	0.430 (4)
C7B	0.7724 (9)	0.5082 (8)	0.53851 (19)	0.0311 (8)	0.430 (4)
H7B	0.8108	0.4585	0.5177	0.037*	0.430 (4)
C8B	0.8067 (7)	0.4998 (7)	0.5786 (2)	0.0392 (15)	0.430 (4)
H8B	0.8656	0.4388	0.5910	0.047*	0.430 (4)
C9B	0.7390 (6)	0.5956 (6)	0.59554 (18)	0.0405 (9)	0.430 (4)
H9B	0.7454	0.6149	0.6229	0.049*	0.430 (4)
O2BB	0.7728 (4)	0.5083 (4)	0.52700 (8)	0.0347 (6)	0.570 (4)
C6BB	0.6943 (19)	0.613 (2)	0.5349 (6)	0.023 (2)	0.570 (4)
C7BB	0.6920 (4)	0.6323 (4)	0.57507 (17)	0.0311 (8)	0.570 (4)
H7BB	0.6370	0.6936	0.5887	0.037*	0.570 (4)
C8BB	0.7856 (5)	0.5455 (5)	0.59227 (13)	0.0392 (15)	0.570 (4)
H8BB	0.8115	0.5390	0.6193	0.047*	0.570 (4)
C9BB	0.8307 (4)	0.4732 (4)	0.56174 (14)	0.0405 (9)	0.570 (4)
H9BB	0.8958	0.4054	0.5644	0.049*	0.570 (4)
N1B	0.62643 (12)	0.65199 (13)	0.46545 (3)	0.0251 (3)
N2B	0.69338 (13)	0.67832 (11)	0.38373 (3)	0.0233 (3)
H2BA	0.7311	0.7252	0.3607	0.028*
H2BB	0.6603	0.5938	0.3745	0.028*
C1B	0.75009 (15)	0.58881 (15)	0.44944 (4)	0.0248 (3)
H1BA	0.7264	0.5001	0.4417	0.030*
H1BB	0.8233	0.5849	0.4700	0.030*
C2B	0.80476 (15)	0.66087 (15)	0.41378 (4)	0.0262 (3)
H2BC	0.8400	0.7456	0.4222	0.031*
H2BD	0.8832	0.6128	0.4020	0.031*
C3B	0.57552 (16)	0.75100 (15)	0.40107 (4)	0.0273 (3)
H3BA	0.5016	0.7624	0.3810	0.033*
H3BB	0.6079	0.8367	0.4094	0.033*
C4B	0.51769 (15)	0.67938 (17)	0.43631 (4)	0.0301 (4)
H4BA	0.4435	0.7311	0.4488	0.036*
H4BB	0.4756	0.5980	0.4273	0.036*
C5B	0.59507 (16)	0.66629 (16)	0.50423 (4)	0.0299 (4)

	U11	U22	U33	U12	U13	U23
O1A	0.0419 (6)	0.0242 (5)	0.0189 (5)	0.0007 (4)	−0.0049 (4)	−0.0006 (4)
O2A	0.0430 (6)	0.0275 (6)	0.0246 (5)	0.0102 (5)	−0.0106 (4)	−0.0032 (4)
O3A	0.0509 (8)	0.0651 (9)	0.0228 (6)	0.0221 (7)	0.0003 (5)	−0.0018 (5)
O4A	0.0528 (8)	0.0454 (7)	0.0262 (6)	0.0075 (6)	−0.0137 (5)	0.0072 (5)
O5A	0.0365 (7)	0.0445 (7)	0.0560 (8)	0.0169 (6)	−0.0095 (6)	−0.0018 (6)
O6A	0.0505 (8)	0.0472 (8)	0.0427 (7)	0.0127 (6)	0.0179 (6)	0.0016 (6)
N1A	0.0314 (6)	0.0315 (7)	0.0216 (6)	−0.0008 (5)	−0.0046 (5)	0.0036 (5)
N2A	0.0269 (6)	0.0275 (7)	0.0433 (8)	0.0004 (5)	0.0028 (6)	0.0001 (6)
C1A	0.0305 (7)	0.0198 (7)	0.0214 (7)	−0.0021 (6)	−0.0054 (6)	0.0016 (5)
C2A	0.0249 (7)	0.0206 (7)	0.0218 (7)	−0.0045 (5)	−0.0035 (5)	0.0024 (5)
C3A	0.0233 (7)	0.0204 (7)	0.0233 (7)	−0.0013 (5)	−0.0028 (5)	0.0001 (5)
C4A	0.0252 (7)	0.0240 (7)	0.0207 (6)	−0.0041 (6)	−0.0027 (5)	0.0023 (5)
C5A	0.0234 (7)	0.0235 (7)	0.0287 (7)	−0.0017 (5)	−0.0057 (6)	0.0043 (6)
C6A	0.0223 (7)	0.0224 (7)	0.0316 (7)	−0.0014 (5)	−0.0004 (6)	0.0009 (6)
C7A	0.0268 (7)	0.0238 (7)	0.0215 (7)	−0.0038 (6)	−0.0004 (5)	−0.0007 (5)
O1B	0.0552 (8)	0.0842 (11)	0.0278 (6)	0.0375 (8)	0.0117 (6)	0.0020 (6)
O2B	0.0447 (11)	0.0406 (11)	0.0188 (11)	0.0075 (8)	−0.0056 (12)	0.0038 (13)
C6B	0.019 (5)	0.029 (3)	0.0200 (7)	−0.010 (4)	0.003 (3)	0.0016 (14)
C7B	0.0344 (14)	0.0367 (15)	0.022 (2)	0.0009 (11)	−0.0054 (17)	0.0024 (18)
C8B	0.044 (2)	0.049 (3)	0.024 (2)	−0.016 (3)	−0.017 (2)	0.015 (2)
C9B	0.0447 (16)	0.0482 (18)	0.0284 (14)	−0.0067 (13)	−0.0148 (15)	0.0141 (16)
O2BB	0.0447 (11)	0.0406 (11)	0.0188 (11)	0.0075 (8)	−0.0056 (12)	0.0038 (13)
C6BB	0.019 (5)	0.029 (3)	0.0200 (7)	−0.010 (4)	0.003 (3)	0.0016 (14)
C7BB	0.0344 (14)	0.0367 (15)	0.022 (2)	0.0009 (11)	−0.0054 (17)	0.0024 (18)
C8BB	0.044 (2)	0.049 (3)	0.024 (2)	−0.016 (3)	−0.017 (2)	0.015 (2)
C9BB	0.0447 (16)	0.0482 (18)	0.0284 (14)	−0.0067 (13)	−0.0148 (15)	0.0141 (16)
N1B	0.0236 (6)	0.0343 (7)	0.0174 (6)	0.0045 (5)	0.0012 (4)	0.0017 (5)
N2B	0.0292 (6)	0.0245 (6)	0.0163 (5)	−0.0049 (5)	0.0008 (5)	0.0003 (4)
C1B	0.0267 (7)	0.0294 (7)	0.0184 (6)	0.0052 (6)	0.0015 (5)	−0.0009 (5)
C2B	0.0242 (7)	0.0351 (8)	0.0192 (7)	−0.0006 (6)	0.0010 (5)	−0.0008 (6)
C3B	0.0303 (7)	0.0289 (7)	0.0227 (7)	0.0020 (6)	−0.0026 (6)	0.0030 (6)
C4B	0.0233 (7)	0.0444 (9)	0.0227 (7)	0.0024 (6)	0.0003 (6)	0.0059 (6)
C5B	0.0330 (8)	0.0354 (8)	0.0212 (7)	0.0056 (7)	0.0042 (6)	0.0007 (6)

O1A—C1A	1.2539 (17)	C9B—H9B	0.9500
O2A—C1A	1.2529 (18)	O2BB—C6BB	1.35 (3)
O3A—N1A	1.2261 (18)	O2BB—C9BB	1.352 (5)
O4A—N1A	1.2173 (17)	C6BB—C7BB	1.38 (2)
O5A—N2A	1.2251 (19)	C6BB—C5B	1.517 (9)
O6A—N2A	1.2220 (19)	C7BB—H7BB	0.9500
N1A—C4A	1.4722 (18)	C7BB—C8BB	1.405 (6)
N2A—C6A	1.4741 (19)	C8BB—H8BB	0.9500
C1A—C2A	1.5208 (19)	C8BB—C9BB	1.352 (6)
C2A—C3A	1.3905 (19)	C9BB—H9BB	0.9500
C2A—C7A	1.386 (2)	N1B—C1B	1.4634 (18)
C3A—H3A	0.9500	N1B—C4B	1.4656 (18)
C3A—C4A	1.387 (2)	N1B—C5B	1.3563 (19)
C4A—C5A	1.383 (2)	N2B—H2BA	0.9900
C5A—H5A	0.9500	N2B—H2BB	0.9900
C5A—C6A	1.380 (2)	N2B—C2B	1.4880 (18)
C6A—C7A	1.386 (2)	N2B—C3B	1.4848 (19)
C7A—H7A	0.9500	C1B—H1BA	0.9900
O1B—C5B	1.226 (2)	C1B—H1BB	0.9900
O2B—C6B	1.36 (3)	C1B—C2B	1.5178 (19)
O2B—C9B	1.342 (6)	C2B—H2BC	0.9900
C6B—C7B	1.38 (3)	C2B—H2BD	0.9900
C6B—C5B	1.444 (12)	C3B—H3BA	0.9900
C7B—H7B	0.9500	C3B—H3BB	0.9900
C7B—C8B	1.401 (8)	C3B—C4B	1.515 (2)
C8B—H8B	0.9500	C4B—H4BA	0.9900
C8B—C9B	1.325 (9)	C4B—H4BB	0.9900
O3A—N1A—C4A	117.76 (12)	C8BB—C7BB—H7BB	126.2
O4A—N1A—O3A	123.46 (13)	C7BB—C8BB—H8BB	127.8
O4A—N1A—C4A	118.78 (13)	C9BB—C8BB—C7BB	104.4 (4)
O5A—N2A—C6A	117.39 (14)	C9BB—C8BB—H8BB	127.8
O6A—N2A—O5A	124.34 (14)	O2BB—C9BB—H9BB	123.7
O6A—N2A—C6A	118.27 (13)	C8BB—C9BB—O2BB	112.5 (4)
O1A—C1A—C2A	116.97 (13)	C8BB—C9BB—H9BB	123.7
O2A—C1A—O1A	126.19 (13)	C1B—N1B—C4B	114.66 (11)
O2A—C1A—C2A	116.84 (12)	C5B—N1B—C1B	126.09 (12)
C3A—C2A—C1A	120.16 (13)	C5B—N1B—C4B	118.21 (12)
C7A—C2A—C1A	119.94 (13)	H2BA—N2B—H2BB	108.2
C7A—C2A—C3A	119.88 (13)	C2B—N2B—H2BA	109.7
C2A—C3A—H3A	120.7	C2B—N2B—H2BB	109.7
C4A—C3A—C2A	118.65 (13)	C3B—N2B—H2BA	109.7
C4A—C3A—H3A	120.7	C3B—N2B—H2BB	109.7
C3A—C4A—N1A	118.53 (13)	C3B—N2B—C2B	109.90 (11)
C5A—C4A—N1A	118.11 (12)	N1B—C1B—H1BA	109.5
C5A—C4A—C3A	123.36 (13)	N1B—C1B—H1BB	109.5
C4A—C5A—H5A	122.1	N1B—C1B—C2B	110.59 (12)
C6A—C5A—C4A	115.85 (13)	H1BA—C1B—H1BB	108.1
C6A—C5A—H5A	122.1	C2B—C1B—H1BA	109.5
C5A—C6A—N2A	118.44 (13)	C2B—C1B—H1BB	109.5
C5A—C6A—C7A	123.33 (14)	N2B—C2B—C1B	110.90 (12)
C7A—C6A—N2A	118.22 (13)	N2B—C2B—H2BC	109.5
C2A—C7A—C6A	118.91 (13)	N2B—C2B—H2BD	109.5
C2A—C7A—H7A	120.5	C1B—C2B—H2BC	109.5
C6A—C7A—H7A	120.5	C1B—C2B—H2BD	109.5
C9B—O2B—C6B	105.8 (9)	H2BC—C2B—H2BD	108.0
O2B—C6B—C7B	108.3 (9)	N2B—C3B—H3BA	109.7
O2B—C6B—C5B	112 (2)	N2B—C3B—H3BB	109.7
C7B—C6B—C5B	139 (3)	N2B—C3B—C4B	109.78 (12)
C6B—C7B—H7B	126.5	H3BA—C3B—H3BB	108.2
C6B—C7B—C8B	107.1 (13)	C4B—C3B—H3BA	109.7
C8B—C7B—H7B	126.5	C4B—C3B—H3BB	109.7
C7B—C8B—H8B	127.6	N1B—C4B—C3B	111.47 (12)
C9B—C8B—C7B	104.9 (5)	N1B—C4B—H4BA	109.3
C9B—C8B—H8B	127.6	N1B—C4B—H4BB	109.3
O2B—C9B—H9B	123.4	C3B—C4B—H4BA	109.3
C8B—C9B—O2B	113.2 (5)	C3B—C4B—H4BB	109.3
C8B—C9B—H9B	123.4	H4BA—C4B—H4BB	108.0
C6BB—O2BB—C9BB	106.0 (7)	O1B—C5B—C6B	115.6 (15)
O2BB—C6BB—C7BB	109.0 (7)	O1B—C5B—C6BB	119.1 (10)
O2BB—C6BB—C5B	120.9 (17)	O1B—C5B—N1B	121.96 (15)
C7BB—C6BB—C5B	127.6 (18)	N1B—C5B—C6B	122.1 (15)
C6BB—C7BB—H7BB	126.2	N1B—C5B—C6BB	118.8 (10)
C6BB—C7BB—C8BB	107.6 (9)
O1A—C1A—C2A—C3A	−169.82 (13)	C7B—C6B—C5B—N1B	−10 (4)
O1A—C1A—C2A—C7A	11.8 (2)	C7B—C8B—C9B—O2B	2.0 (7)
O2A—C1A—C2A—C3A	10.2 (2)	C9B—O2B—C6B—C7B	−8 (2)
O2A—C1A—C2A—C7A	−168.20 (14)	C9B—O2B—C6B—C5B	−178.6 (14)
O3A—N1A—C4A—C3A	−1.9 (2)	O2BB—C6BB—C7BB—C8BB	6.9 (14)
O3A—N1A—C4A—C5A	178.35 (15)	O2BB—C6BB—C5B—O1B	153.1 (11)
O4A—N1A—C4A—C3A	177.96 (14)	O2BB—C6BB—C5B—C6B	85 (17)
O4A—N1A—C4A—C5A	−1.8 (2)	O2BB—C6BB—C5B—N1B	−29.8 (18)
O5A—N2A—C6A—C5A	4.4 (2)	C6BB—O2BB—C9BB—C8BB	4.1 (10)
O5A—N2A—C6A—C7A	−176.94 (14)	C6BB—C7BB—C8BB—C9BB	−4.2 (10)
O6A—N2A—C6A—C5A	−175.20 (14)	C7BB—C6BB—C5B—O1B	−7 (2)
O6A—N2A—C6A—C7A	3.5 (2)	C7BB—C6BB—C5B—C6B	−75 (17)
N1A—C4A—C5A—C6A	−178.63 (12)	C7BB—C6BB—C5B—N1B	170.0 (13)
N2A—C6A—C7A—C2A	−178.59 (13)	C7BB—C8BB—C9BB—O2BB	0.1 (5)
C1A—C2A—C3A—C4A	−179.95 (12)	C9BB—O2BB—C6BB—C7BB	−6.7 (14)
C1A—C2A—C7A—C6A	179.97 (13)	C9BB—O2BB—C6BB—C5B	−170.1 (11)
C2A—C3A—C4A—N1A	−179.82 (12)	N1B—C1B—C2B—N2B	−54.25 (16)
C2A—C3A—C4A—C5A	−0.1 (2)	N2B—C3B—C4B—N1B	55.11 (17)
C3A—C2A—C7A—C6A	1.6 (2)	C1B—N1B—C4B—C3B	−52.13 (18)
C3A—C4A—C5A—C6A	1.6 (2)	C1B—N1B—C5B—O1B	176.66 (17)
C4A—C5A—C6A—N2A	177.02 (13)	C1B—N1B—C5B—C6B	−9.7 (15)
C4A—C5A—C6A—C7A	−1.6 (2)	C1B—N1B—C5B—C6BB	−0.3 (10)
C5A—C6A—C7A—C2A	0.0 (2)	C2B—N2B—C3B—C4B	−59.34 (15)
C7A—C2A—C3A—C4A	−1.6 (2)	C3B—N2B—C2B—C1B	59.48 (15)
O2B—C6B—C7B—C8B	9 (2)	C4B—N1B—C1B—C2B	51.18 (17)
O2B—C6B—C5B—O1B	−29 (2)	C4B—N1B—C5B—O1B	−15.7 (3)
O2B—C6B—C5B—C6BB	87 (17)	C4B—N1B—C5B—C6B	157.9 (14)
O2B—C6B—C5B—N1B	157.2 (12)	C4B—N1B—C5B—C6BB	167.3 (10)
C6B—O2B—C9B—C8B	3.4 (14)	C5B—C6B—C7B—C8B	176 (3)
C6B—C7B—C8B—C9B	−6.6 (14)	C5B—C6BB—C7BB—C8BB	168.9 (14)
C7B—C6B—C5B—O1B	164 (3)	C5B—N1B—C1B—C2B	−140.79 (15)
C7B—C6B—C5B—C6BB	−80 (17)	C5B—N1B—C4B—C3B	138.83 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N2B—H2BA···O1Ai	0.99	2.51	3.1607 (16)	123
N2B—H2BA···O2Ai	0.99	1.72	2.7093 (16)	176
N2B—H2BB···O1Aii	0.99	1.77	2.7424 (16)	166
C5A—H5A···O2Aiii	0.95	2.47	3.3170 (18)	148
C9B—H9B···O6Aiv	0.95	2.44	3.183 (6)	134
C8BB—H8BB···O3Av	0.95	2.50	3.395 (5)	158
C2B—H2BC···O1Bi	0.99	2.59	3.2300 (19)	122

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2B—H2BA⋯O1A i	0.99	2.51	3.1607 (16)	123
N2B—H2BA⋯O2A i	0.99	1.72	2.7093 (16)	176
N2B—H2BB⋯O1A ii	0.99	1.77	2.7424 (16)	166
C5A—H5A⋯O2A iii	0.95	2.47	3.3170 (18)	148
C9B—H9B⋯O6A iv	0.95	2.44	3.183 (6)	134
C8BB—H8BB⋯O3A v	0.95	2.50	3.395 (5)	158
C2B—H2BC⋯O1B i	0.99	2.59	3.2300 (19)	122

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