m-Xylylenediaminium dinitrate.

The asymmetric unit of the title salt, C8H14N2 (2+)·2NO3 (-), contains two independent dications and four independent nitrate anions. The crystal structure consists of discrete nitrate ions, three of which stack in layers parallel to (001) at z = 0 and 0.5. These layers are connected via m-xylylenediaminium dications. The fourth anion is sandwiched by the two independent organic cations in the asymmetric unit. In the crystal, the ions are connected by a large number of bifurcated and non-bifurcated N-H⋯O(O) hydrogen bonds, forming sheets parallel to (100). These sheets are connected by C-H⋯O hydrogen bonds, forming a three-dimensional network.

Related literature

For related nitrate salts, see: Gatfaoui et al. (2013 ▶, 2014 ▶); Marouani et al. (2012 ▶); Kefi et al. (2013 ▶). For the dichloride salt of the title cation, see: Cheng & Li (2008 ▶). For background to hydrogen bonding and aromatic π–π stacking inter­actions, see: Brown (1976 ▶); Blessing (1986 ▶); Janiak (2000 ▶).

Experimental

Crystal data

C8H14N2 2+·2NO3 −

M = 262.23

Monoclinic,

a = 21.4308 (7) Å

b = 5.7255 (2) Å

c = 20.4476 (5) Å

β = 108.502 (1)°

V = 2379.28 (13) Å3

Z = 8

Mo Kα radiation

μ = 0.13 mm−1

T = 150 K

0.47 × 0.24 × 0.17 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2006 ▶) T min = 0.889, T max = 0.979

19108 measured reflections

5457 independent reflections

4429 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.129

S = 1.04

5457 reflections

329 parameters

H-atom parameters constrained

Δρmax = 0.51 e Å−3

Δρmin = −0.28 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and CRYSCAL (T. Roisnel, local program).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814004620/bh2495sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814004620/bh2495Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814004620/bh2495Isup3.cml

CCDC reference: 989215

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

C8H14N22+·2NO3−	F(000) = 1104
Mr = 262.23	Dx = 1.464 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6173 reflections
a = 21.4308 (7) Å	θ = 3.0–27.3°
b = 5.7255 (2) Å	µ = 0.13 mm−1
c = 20.4476 (5) Å	T = 150 K
β = 108.502 (1)°	Prism, colourless
V = 2379.28 (13) Å3	0.47 × 0.24 × 0.17 mm
Z = 8

Bruker APEXII diffractometer	4429 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
CCD rotation images, thin slices scans	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 2006)	h = −26→22
Tmin = 0.889, Tmax = 0.979	k = −6→7
19108 measured reflections	l = −27→27
5457 independent reflections

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.129	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0626P)2 + 1.0374P] where P = (Fo2 + 2Fc2)/3
5457 reflections	(Δ/σ)max = 0.003
329 parameters	Δρmax = 0.51 e Å−3
0 restraints	Δρmin = −0.28 e Å−3
0 constraints

	x	y	z	Uiso*/Ueq
N1	0.26601 (6)	0.0292 (2)	0.14220 (7)	0.0272 (3)
H1A	0.2554	−0.1199	0.1498	0.041*
H1B	0.2374	0.0818	0.1018	0.041*
H1C	0.2635	0.1223	0.1774	0.041*
C1	0.33450 (8)	0.0351 (3)	0.13828 (9)	0.0329 (4)
H1D	0.3490	0.1991	0.1376	0.040*
H1E	0.3356	−0.0416	0.0953	0.040*
C2	0.38017 (7)	−0.0900 (3)	0.19976 (8)	0.0221 (3)
C3	0.40757 (7)	−0.3050 (3)	0.19264 (8)	0.0236 (3)
H3	0.3998	−0.3709	0.1481	0.028*
C4	0.44632 (7)	−0.4234 (3)	0.25056 (9)	0.0229 (3)
H4	0.4656	−0.5688	0.2453	0.027*
C5	0.45719 (7)	−0.3312 (3)	0.31598 (8)	0.0215 (3)
H5	0.4827	−0.4153	0.3555	0.026*
C6	0.43055 (7)	−0.1149 (3)	0.32352 (8)	0.0198 (3)
C7	0.39272 (7)	0.0044 (3)	0.26535 (8)	0.0208 (3)
H7	0.3751	0.1530	0.2704	0.025*
C8	0.43934 (8)	−0.0113 (3)	0.39380 (9)	0.0278 (4)
H8A	0.4758	−0.0919	0.4288	0.033*
H8B	0.4508	0.1561	0.3938	0.033*
N2	0.37725 (7)	−0.0370 (3)	0.41183 (7)	0.0270 (3)
H2A	0.3426	0.0137	0.3760	0.041*
H2B	0.3802	0.0495	0.4500	0.041*
H2C	0.3713	−0.1899	0.4204	0.041*
N3	0.12089 (6)	−0.4473 (2)	0.08345 (7)	0.0215 (3)
H3A	0.1231	−0.2923	0.0746	0.032*
H3B	0.1162	−0.5304	0.0442	0.032*
H3C	0.1585	−0.4920	0.1166	0.032*
C9	0.06349 (8)	−0.4918 (3)	0.10789 (9)	0.0267 (4)
H9A	0.0552	−0.6620	0.1076	0.032*
H9B	0.0239	−0.4169	0.0759	0.032*
C10	0.07523 (7)	−0.3980 (3)	0.17964 (8)	0.0195 (3)
C11	0.04955 (7)	−0.1832 (3)	0.19040 (8)	0.0205 (3)
H11	0.0256	−0.0906	0.1521	0.025*
C12	0.05893 (7)	−0.1046 (3)	0.25702 (9)	0.0234 (3)
H12	0.0410	0.0413	0.2642	0.028*
C13	0.09441 (8)	−0.2383 (3)	0.31318 (8)	0.0248 (3)
H13	0.1005	−0.1838	0.3587	0.030*
C14	0.12113 (7)	−0.4520 (3)	0.30315 (8)	0.0242 (3)
C15	0.11106 (7)	−0.5290 (3)	0.23635 (8)	0.0216 (3)
H15	0.1291	−0.6747	0.2291	0.026*
C16	0.15782 (8)	−0.6046 (4)	0.36295 (10)	0.0368 (4)
H16A	0.1348	−0.6021	0.3979	0.044*
H16B	0.1575	−0.7675	0.3466	0.044*
N4	0.22723 (6)	−0.5286 (2)	0.39575 (7)	0.0227 (3)
H4A	0.2492	−0.5372	0.3644	0.034*
H4B	0.2470	−0.6234	0.4322	0.034*
H4C	0.2279	−0.3787	0.4108	0.034*
N5	0.26305 (6)	−0.4703 (3)	0.24641 (7)	0.0287 (3)
O1	0.26758 (7)	−0.2898 (3)	0.28036 (7)	0.0436 (4)
O2	0.26855 (6)	−0.6677 (3)	0.27431 (7)	0.0415 (3)
O3	0.25175 (6)	−0.4589 (2)	0.18215 (6)	0.0350 (3)
N6	0.08581 (6)	0.0558 (2)	−0.00143 (7)	0.0236 (3)
O4	0.07924 (6)	0.2525 (2)	−0.03009 (6)	0.0283 (3)
O5	0.05713 (7)	−0.1176 (2)	−0.03262 (6)	0.0391 (3)
O6	0.12308 (5)	0.03715 (19)	0.06066 (6)	0.0246 (3)
N7	0.23961 (6)	−0.4784 (2)	−0.00724 (7)	0.0219 (3)
O7	0.22667 (7)	−0.3051 (2)	0.02227 (7)	0.0402 (3)
O8	0.24994 (6)	−0.4545 (2)	−0.06438 (6)	0.0290 (3)
O9	0.24162 (6)	−0.6782 (2)	0.01751 (6)	0.0346 (3)
N8	0.40614 (7)	0.0407 (3)	0.00192 (7)	0.0279 (3)
O10	0.37062 (6)	0.0189 (2)	−0.06046 (6)	0.0332 (3)
O11	0.43303 (8)	−0.1319 (3)	0.03493 (7)	0.0481 (4)
O12	0.41292 (6)	0.2396 (2)	0.02899 (6)	0.0347 (3)

	U11	U22	U33	U12	U13	U23
N1	0.0203 (6)	0.0296 (8)	0.0274 (7)	0.0020 (5)	0.0012 (5)	0.0040 (6)
C1	0.0228 (8)	0.0458 (11)	0.0301 (9)	0.0040 (7)	0.0082 (7)	0.0153 (8)
C2	0.0159 (7)	0.0263 (8)	0.0237 (8)	−0.0021 (6)	0.0056 (6)	0.0068 (6)
C3	0.0215 (7)	0.0271 (8)	0.0233 (8)	−0.0056 (6)	0.0086 (6)	−0.0042 (7)
C4	0.0222 (7)	0.0159 (7)	0.0332 (9)	−0.0007 (6)	0.0126 (6)	−0.0017 (6)
C5	0.0173 (7)	0.0213 (8)	0.0257 (8)	0.0015 (6)	0.0063 (6)	0.0059 (6)
C6	0.0152 (6)	0.0218 (7)	0.0226 (7)	−0.0026 (6)	0.0062 (5)	−0.0019 (6)
C7	0.0167 (7)	0.0163 (7)	0.0307 (8)	0.0012 (5)	0.0093 (6)	0.0023 (6)
C8	0.0214 (7)	0.0342 (9)	0.0277 (8)	−0.0031 (7)	0.0076 (6)	−0.0080 (7)
N2	0.0245 (7)	0.0318 (8)	0.0266 (7)	0.0001 (6)	0.0106 (6)	−0.0073 (6)
N3	0.0225 (6)	0.0219 (7)	0.0205 (6)	−0.0001 (5)	0.0073 (5)	−0.0005 (5)
C9	0.0220 (7)	0.0303 (9)	0.0290 (9)	−0.0045 (6)	0.0100 (6)	−0.0094 (7)
C10	0.0167 (7)	0.0191 (7)	0.0240 (8)	−0.0035 (5)	0.0083 (6)	−0.0023 (6)
C11	0.0177 (7)	0.0185 (7)	0.0247 (8)	−0.0015 (5)	0.0061 (6)	0.0030 (6)
C12	0.0213 (7)	0.0187 (7)	0.0328 (9)	−0.0016 (6)	0.0121 (6)	−0.0045 (7)
C13	0.0224 (7)	0.0298 (8)	0.0232 (8)	−0.0072 (6)	0.0089 (6)	−0.0041 (7)
C14	0.0167 (7)	0.0282 (8)	0.0266 (8)	−0.0044 (6)	0.0053 (6)	0.0089 (7)
C15	0.0169 (7)	0.0161 (7)	0.0329 (9)	0.0000 (5)	0.0095 (6)	0.0016 (6)
C16	0.0233 (8)	0.0447 (11)	0.0379 (10)	−0.0055 (8)	0.0032 (7)	0.0207 (9)
N4	0.0243 (6)	0.0205 (6)	0.0205 (7)	0.0010 (5)	0.0033 (5)	0.0015 (5)
N5	0.0175 (6)	0.0420 (9)	0.0270 (7)	−0.0025 (6)	0.0077 (5)	−0.0016 (7)
O1	0.0410 (8)	0.0502 (9)	0.0449 (8)	−0.0155 (6)	0.0210 (6)	−0.0169 (7)
O2	0.0359 (7)	0.0463 (8)	0.0471 (8)	0.0113 (6)	0.0200 (6)	0.0128 (7)
O3	0.0266 (6)	0.0554 (8)	0.0228 (6)	−0.0075 (6)	0.0077 (5)	−0.0010 (6)
N6	0.0241 (7)	0.0254 (7)	0.0209 (7)	0.0023 (5)	0.0067 (5)	−0.0019 (6)
O4	0.0364 (6)	0.0253 (6)	0.0220 (6)	0.0069 (5)	0.0073 (5)	0.0029 (5)
O5	0.0484 (8)	0.0304 (7)	0.0296 (7)	−0.0083 (6)	−0.0002 (6)	−0.0073 (6)
O6	0.0269 (6)	0.0243 (6)	0.0186 (5)	0.0021 (4)	0.0013 (4)	−0.0001 (5)
N7	0.0217 (6)	0.0213 (7)	0.0212 (7)	−0.0024 (5)	0.0046 (5)	−0.0005 (5)
O7	0.0586 (9)	0.0290 (7)	0.0412 (7)	−0.0008 (6)	0.0275 (7)	−0.0099 (6)
O8	0.0389 (7)	0.0267 (6)	0.0250 (6)	−0.0006 (5)	0.0152 (5)	0.0014 (5)
O9	0.0478 (8)	0.0246 (6)	0.0266 (6)	−0.0043 (5)	0.0051 (5)	0.0072 (5)
N8	0.0237 (7)	0.0338 (8)	0.0251 (7)	−0.0016 (6)	0.0063 (6)	0.0087 (6)
O10	0.0302 (6)	0.0347 (7)	0.0261 (6)	−0.0003 (5)	−0.0034 (5)	0.0037 (5)
O11	0.0600 (9)	0.0416 (8)	0.0322 (7)	0.0123 (7)	−0.0005 (6)	0.0127 (6)
O12	0.0406 (7)	0.0324 (7)	0.0282 (6)	−0.0058 (5)	0.0070 (5)	0.0025 (5)

N1—C1	1.495 (2)	C9—H9B	0.9900
N1—H1A	0.9100	C10—C15	1.390 (2)
N1—H1B	0.9100	C10—C11	1.393 (2)
N1—H1C	0.9100	C11—C12	1.388 (2)
C1—C2	1.507 (2)	C11—H11	0.9500
C1—H1D	0.9900	C12—C13	1.389 (2)
C1—H1E	0.9900	C12—H12	0.9500
C2—C7	1.391 (2)	C13—C14	1.393 (2)
C2—C3	1.392 (2)	C13—H13	0.9500
C3—C4	1.388 (2)	C14—C15	1.386 (2)
C3—H3	0.9500	C14—C16	1.506 (2)
C4—C5	1.387 (2)	C15—H15	0.9500
C4—H4	0.9500	C16—N4	1.489 (2)
C5—C6	1.393 (2)	C16—H16A	0.9900
C5—H5	0.9500	C16—H16B	0.9900
C6—C7	1.388 (2)	N4—H4A	0.9100
C6—C8	1.510 (2)	N4—H4B	0.9100
C7—H7	0.9500	N4—H4C	0.9100
C8—N2	1.496 (2)	N5—O1	1.2314 (19)
C8—H8A	0.9900	N5—O2	1.255 (2)
C8—H8B	0.9900	N5—O3	1.2599 (18)
N2—H2A	0.9100	N6—O4	1.2566 (17)
N2—H2B	0.9100	N6—O5	1.2334 (18)
N2—H2C	0.9100	N6—O6	1.2719 (17)
N3—C9	1.489 (2)	N7—O7	1.2379 (18)
N3—H3A	0.9100	N7—O8	1.2637 (17)
N3—H3B	0.9100	N7—O9	1.2459 (17)
N3—H3C	0.9100	N8—O10	1.2671 (18)
C9—C10	1.507 (2)	N8—O11	1.2321 (19)
C9—H9A	0.9900	N8—O12	1.2542 (19)
C1—N1—H1A	109.5	N3—C9—C10	111.42 (12)
C1—N1—H1B	109.5	N3—C9—H9A	109.3
H1A—N1—H1B	109.5	C10—C9—H9A	109.3
C1—N1—H1C	109.5	N3—C9—H9B	109.3
H1A—N1—H1C	109.5	C10—C9—H9B	109.3
H1B—N1—H1C	109.5	H9A—C9—H9B	108.0
N1—C1—C2	109.48 (13)	C15—C10—C11	119.09 (14)
N1—C1—H1D	109.8	C15—C10—C9	119.82 (14)
C2—C1—H1D	109.8	C11—C10—C9	121.08 (14)
N1—C1—H1E	109.8	C12—C11—C10	120.02 (14)
C2—C1—H1E	109.8	C12—C11—H11	120.0
H1D—C1—H1E	108.2	C10—C11—H11	120.0
C7—C2—C3	119.06 (14)	C11—C12—C13	120.23 (15)
C7—C2—C1	119.72 (15)	C11—C12—H12	119.9
C3—C2—C1	121.14 (15)	C13—C12—H12	119.9
C4—C3—C2	120.05 (14)	C12—C13—C14	120.34 (15)
C4—C3—H3	120.0	C12—C13—H13	119.8
C2—C3—H3	120.0	C14—C13—H13	119.8
C5—C4—C3	120.59 (15)	C15—C14—C13	118.81 (14)
C5—C4—H4	119.7	C15—C14—C16	119.58 (16)
C3—C4—H4	119.7	C13—C14—C16	121.55 (16)
C4—C5—C6	119.72 (14)	C14—C15—C10	121.51 (14)
C4—C5—H5	120.1	C14—C15—H15	119.2
C6—C5—H5	120.1	C10—C15—H15	119.2
C7—C6—C5	119.42 (14)	N4—C16—C14	112.69 (13)
C7—C6—C8	119.01 (14)	N4—C16—H16A	109.1
C5—C6—C8	121.52 (14)	C14—C16—H16A	109.1
C6—C7—C2	121.13 (14)	N4—C16—H16B	109.1
C6—C7—H7	119.4	C14—C16—H16B	109.1
C2—C7—H7	119.4	H16A—C16—H16B	107.8
N2—C8—C6	110.10 (12)	C16—N4—H4A	109.5
N2—C8—H8A	109.6	C16—N4—H4B	109.5
C6—C8—H8A	109.6	H4A—N4—H4B	109.5
N2—C8—H8B	109.6	C16—N4—H4C	109.5
C6—C8—H8B	109.6	H4A—N4—H4C	109.5
H8A—C8—H8B	108.2	H4B—N4—H4C	109.5
C8—N2—H2A	109.5	O1—N5—O2	121.35 (15)
C8—N2—H2B	109.5	O1—N5—O3	119.95 (15)
H2A—N2—H2B	109.5	O2—N5—O3	118.69 (15)
C8—N2—H2C	109.5	O4—N6—O6	118.86 (13)
H2A—N2—H2C	109.5	O5—N6—O4	121.10 (13)
H2B—N2—H2C	109.5	O5—N6—O6	120.04 (13)
C9—N3—H3A	109.5	O7—N7—O9	121.48 (13)
C9—N3—H3B	109.5	O7—N7—O8	119.70 (13)
H3A—N3—H3B	109.5	O9—N7—O8	118.80 (13)
C9—N3—H3C	109.5	O11—N8—O12	121.20 (14)
H3A—N3—H3C	109.5	O11—N8—O10	119.97 (15)
H3B—N3—H3C	109.5	O12—N8—O10	118.83 (14)
N1—C1—C2—C7	−67.34 (19)	N3—C9—C10—C15	−82.48 (18)
N1—C1—C2—C3	109.35 (17)	N3—C9—C10—C11	98.88 (16)
C7—C2—C3—C4	0.6 (2)	C15—C10—C11—C12	−1.1 (2)
C1—C2—C3—C4	−176.12 (14)	C9—C10—C11—C12	177.56 (14)
C2—C3—C4—C5	1.2 (2)	C10—C11—C12—C13	0.6 (2)
C3—C4—C5—C6	−1.8 (2)	C11—C12—C13—C14	0.3 (2)
C4—C5—C6—C7	0.8 (2)	C12—C13—C14—C15	−0.7 (2)
C4—C5—C6—C8	178.08 (14)	C12—C13—C14—C16	−177.88 (14)
C5—C6—C7—C2	1.0 (2)	C13—C14—C15—C10	0.1 (2)
C8—C6—C7—C2	−176.39 (13)	C16—C14—C15—C10	177.42 (14)
C3—C2—C7—C6	−1.7 (2)	C11—C10—C15—C14	0.7 (2)
C1—C2—C7—C6	175.10 (14)	C9—C10—C15—C14	−177.94 (13)
C7—C6—C8—N2	73.72 (19)	C15—C14—C16—N4	102.05 (19)
C5—C6—C8—N2	−103.59 (16)	C13—C14—C16—N4	−80.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O3	0.91	2.06	2.9545 (16)	168
N1—H1B···O6	0.91	2.34	2.9872 (18)	128
N1—H1B···O9i	0.91	2.23	2.9554 (17)	137
N1—H1C···O2i	0.91	2.29	3.197 (2)	173
N1—H1C···O3i	0.91	2.42	3.0837 (16)	130
N2—H2B···O10ii	0.91	2.48	3.032 (2)	119
N2—H2B···O12ii	0.91	1.96	2.8391 (19)	162
N2—H2C···O10iii	0.91	1.92	2.829 (2)	173
N2—H2C···O11iii	0.91	2.51	3.074 (2)	120
N3—H3A···O5	0.91	2.42	3.0008 (17)	122
N3—H3A···O6	0.91	1.91	2.8155 (16)	175
N3—H3B···O4iv	0.91	1.93	2.7974 (17)	159
N3—H3B···O6iv	0.91	2.50	2.9910 (16)	114
N3—H3C···O3	0.91	2.03	2.8897 (19)	157
N4—H4A···O1	0.91	2.35	3.079 (2)	137
N4—H4A···O2	0.91	2.15	2.9967 (19)	155
N4—H4B···O8v	0.91	2.42	3.0673 (16)	128
N4—H4B···O9v	0.91	2.12	2.9368 (17)	150
N4—H4C···O7iii	0.91	2.52	3.2192 (18)	134
N4—H4C···O8iii	0.91	1.99	2.8810 (16)	165
C7—H7···O2i	0.95	2.53	3.309 (2)	140
C8—H8A···O12vi	0.99	2.46	3.373 (2)	153
C9—H9B···O4vii	0.99	2.31	3.267 (2)	163
C16—H16A···O4iii	0.99	2.33	3.267 (2)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O3	0.91	2.06	2.9545 (16)	168
N1—H1B⋯O6	0.91	2.34	2.9872 (18)	128
N1—H1B⋯O9i	0.91	2.23	2.9554 (17)	137
N1—H1C⋯O2i	0.91	2.29	3.197 (2)	173
N1—H1C⋯O3i	0.91	2.42	3.0837 (16)	130
N2—H2B⋯O10ii	0.91	2.48	3.032 (2)	119
N2—H2B⋯O12ii	0.91	1.96	2.8391 (19)	162
N2—H2C⋯O10iii	0.91	1.92	2.829 (2)	173
N2—H2C⋯O11iii	0.91	2.51	3.074 (2)	120
N3—H3A⋯O5	0.91	2.42	3.0008 (17)	122
N3—H3A⋯O6	0.91	1.91	2.8155 (16)	175
N3—H3B⋯O4iv	0.91	1.93	2.7974 (17)	159
N3—H3B⋯O6iv	0.91	2.50	2.9910 (16)	114
N3—H3C⋯O3	0.91	2.03	2.8897 (19)	157
N4—H4A⋯O1	0.91	2.35	3.079 (2)	137
N4—H4A⋯O2	0.91	2.15	2.9967 (19)	155
N4—H4B⋯O8v	0.91	2.42	3.0673 (16)	128
N4—H4B⋯O9v	0.91	2.12	2.9368 (17)	150
N4—H4C⋯O7iii	0.91	2.52	3.2192 (18)	134
N4—H4C⋯O8iii	0.91	1.99	2.8810 (16)	165
C7—H7⋯O2i	0.95	2.53	3.309 (2)	140
C8—H8A⋯O12vi	0.99	2.46	3.373 (2)	153
C9—H9B⋯O4vii	0.99	2.31	3.267 (2)	163
C16—H16A⋯O4iii	0.99	2.33	3.267 (2)	157

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