Bis(4-amino-pyridinium) dichromate(VI).

The asymmetric unit of the title salt, (C5H7N2)2[Cr2O7], contains four independent cations and two independent dichromate anions. The crystal structure consists of discrete dichromate anions with an eclipsed conformation stacked in layers parallel to (010) at y = 1/4 and y = 3/4. These layers are linked via 4-amino-pyridinium cations by N-H⋯O and weak C-H⋯O hydrogen bonds, forming a three-dimensional supra-molecular network. In addition, π-π inter-actions are present in this structure; the shortest distance separating mean planes through 4-amino-pyridinium cations is 3.679 (6) Å.

Related literature

For properties of pyridine-based compounds, see: Patani & LaVoie (1996 ▶); Ma & Huang (2003 ▶). For related structures, see: Trabelsi et al. (2012 ▶); Lennartson & Håkansson (2009 ▶); Fun et al. (2009 ▶); Ramesh et al. (2010 ▶). For aromatic π–π stacking inter­actions, see: Janiak (2000 ▶).

Experimental

Crystal data

(C5H7N2)2[Cr2O7]

M = 406.25

Monoclinic,

a = 13.8505 (4) Å

b = 16.2486 (4) Å

c = 15.2586 (4) Å

β = 118.923 (2)°

V = 3005.65 (14) Å3

Z = 8

Mo Kα radiation

μ = 1.49 mm−1

T = 150 K

0.58 × 0.5 × 0.4 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2006 ▶) T min = 0.469, T max = 0.552

23461 measured reflections

6868 independent reflections

5506 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.097

S = 1.07

6868 reflections

415 parameters

H-atom parameters constrained

Δρmax = 0.41 e Å−3

Δρmin = −0.58 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: 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, global. DOI: 10.1107/S1600536814013579/bh2500sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814013579/bh2500Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814013579/bh2500Isup3.cml

CCDC reference: 1007743

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

(C5H7N2)2[Cr2O7]	F(000) = 1648
Mr = 406.25	Dx = 1.796 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5472 reflections
a = 13.8505 (4) Å	θ = 2.7–27.3°
b = 16.2486 (4) Å	µ = 1.49 mm−1
c = 15.2586 (4) Å	T = 150 K
β = 118.923 (2)°	Prism, orange
V = 3005.65 (14) Å3	0.58 × 0.5 × 0.4 mm
Z = 8

Bruker APEXII diffractometer	5506 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.042
CCD rotation images, thin slices scans	θmax = 27.5°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 2006)	h = −17→17
Tmin = 0.469, Tmax = 0.552	k = −16→21
23461 measured reflections	l = −17→19
6868 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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0409P)2 + 1.1738P] where P = (Fo2 + 2Fc2)/3
6868 reflections	(Δ/σ)max = 0.001
415 parameters	Δρmax = 0.41 e Å−3
0 restraints	Δρmin = −0.58 e Å−3
0 constraints

	x	y	z	Uiso*/Ueq
Cr1	0.30978 (3)	0.25913 (2)	0.87600 (3)	0.01226 (10)
Cr2	0.14056 (3)	0.25667 (2)	0.64724 (3)	0.01334 (10)
O1	0.36183 (14)	0.34529 (10)	0.86547 (12)	0.0217 (4)
O2	0.37986 (14)	0.18108 (11)	0.87204 (13)	0.0251 (4)
O3	0.30456 (14)	0.25734 (9)	0.97973 (12)	0.0175 (4)
O4	0.16957 (13)	0.25140 (9)	0.77567 (12)	0.0141 (3)
O5	0.25558 (15)	0.24640 (9)	0.64455 (13)	0.0206 (4)
O6	0.05649 (17)	0.18307 (12)	0.58819 (13)	0.0335 (5)
O7	0.08641 (15)	0.34537 (11)	0.60243 (13)	0.0257 (4)
Cr3	0.86884 (3)	0.24904 (2)	0.83351 (3)	0.01316 (10)
Cr4	0.63121 (3)	0.25479 (2)	0.63638 (3)	0.01368 (10)
O8	0.85329 (15)	0.17165 (11)	0.89157 (13)	0.0285 (4)
O9	0.84062 (15)	0.33450 (11)	0.87063 (13)	0.0256 (4)
O10	0.99257 (14)	0.25074 (9)	0.84773 (13)	0.0187 (4)
O11	0.77849 (14)	0.23816 (9)	0.70058 (12)	0.0179 (4)
O12	0.60940 (16)	0.35133 (11)	0.61015 (15)	0.0314 (5)
O13	0.58360 (15)	0.20101 (13)	0.53587 (14)	0.0334 (5)
O14	0.57985 (15)	0.22726 (11)	0.70728 (13)	0.0261 (4)
N1	0.10279 (16)	0.40072 (12)	−0.14295 (15)	0.0211 (5)
HN1	0.0888	0.3498	−0.1597	0.025*
C1	0.1345 (2)	0.45034 (15)	−0.19490 (19)	0.0210 (5)
H1	0.1399	0.4292	−0.2490	0.025*
C2	0.1588 (2)	0.53063 (14)	−0.16971 (18)	0.0179 (5)
H2	0.1804	0.5642	−0.2065	0.021*
C3	0.15119 (19)	0.56323 (14)	−0.08699 (17)	0.0156 (5)
C4	0.11508 (19)	0.50918 (14)	−0.03606 (18)	0.0181 (5)
H4	0.1068	0.5284	0.0174	0.022*
C5	0.0925 (2)	0.42948 (15)	−0.06501 (19)	0.0211 (5)
H5	0.0696	0.3942	−0.0307	0.025*
N2	0.17652 (18)	0.64076 (12)	−0.05892 (16)	0.0237 (5)
H2A	0.1712	0.6594	−0.0087	0.028*
H2B	0.1983	0.6726	−0.0909	0.028*
N3	0.36147 (17)	0.39842 (12)	0.12358 (15)	0.0212 (5)
HN3	0.3460	0.3468	0.1153	0.025*
C6	0.3965 (2)	0.43597 (15)	0.06512 (19)	0.0217 (5)
H6	0.4039	0.4059	0.0168	0.026*
C7	0.4210 (2)	0.51765 (14)	0.07674 (18)	0.0188 (5)
H7	0.4446	0.5433	0.0360	0.023*
C8	0.41064 (18)	0.56376 (14)	0.15032 (17)	0.0154 (5)
C9	0.37277 (19)	0.52161 (15)	0.20893 (17)	0.0176 (5)
H9	0.3633	0.5497	0.2573	0.021*
C10	0.3502 (2)	0.43966 (15)	0.19426 (18)	0.0213 (5)
H10	0.3267	0.4119	0.2338	0.026*
N4	0.43612 (18)	0.64317 (12)	0.16345 (16)	0.0229 (5)
H4A	0.4593	0.6673	0.1269	0.027*
H4B	0.4295	0.6705	0.2085	0.027*
N5	0.66256 (17)	0.60129 (12)	0.39258 (16)	0.0238 (5)
HN5	0.6758	0.6531	0.3940	0.029*
C11	0.6760 (2)	0.55244 (16)	0.32819 (19)	0.0244 (6)
H11	0.6991	0.5753	0.2856	0.029*
C12	0.6565 (2)	0.47016 (15)	0.32428 (18)	0.0190 (5)
H12	0.6668	0.4372	0.2797	0.023*
C13	0.62036 (19)	0.43485 (14)	0.38822 (18)	0.0165 (5)
C14	0.6076 (2)	0.48867 (14)	0.45475 (18)	0.0186 (5)
H14	0.5847	0.4680	0.4986	0.022*
C15	0.6286 (2)	0.57029 (15)	0.45493 (18)	0.0208 (5)
H15	0.6194	0.6052	0.4986	0.025*
N6	0.59854 (18)	0.35547 (12)	0.38491 (17)	0.0243 (5)
H6A	0.5759	0.3352	0.4239	0.029*
H6B	0.6069	0.3240	0.3438	0.029*
N7	0.89889 (16)	0.60146 (12)	0.66303 (15)	0.0190 (4)
HN7	0.9067	0.6532	0.6768	0.023*
C16	0.9173 (2)	0.57268 (15)	0.58964 (18)	0.0193 (5)
H16	0.9388	0.6088	0.5549	0.023*
C17	0.9048 (2)	0.49117 (14)	0.56583 (18)	0.0176 (5)
H17	0.9179	0.4719	0.5152	0.021*
C18	0.87181 (18)	0.43586 (14)	0.61778 (17)	0.0147 (5)
C19	0.8537 (2)	0.46897 (14)	0.69469 (17)	0.0173 (5)
H19	0.8317	0.4348	0.7307	0.021*
C20	0.8684 (2)	0.55068 (14)	0.71542 (18)	0.0193 (5)
H20	0.8574	0.5720	0.7664	0.023*
N8	0.85990 (17)	0.35635 (12)	0.59675 (16)	0.0224 (5)
H8A	0.8723	0.3373	0.5505	0.027*
H8B	0.8398	0.3237	0.6293	0.027*

	U11	U22	U33	U12	U13	U23
Cr1	0.01379 (19)	0.01437 (19)	0.00998 (19)	0.00100 (14)	0.00682 (15)	0.00061 (13)
Cr2	0.0164 (2)	0.0147 (2)	0.01068 (19)	−0.00082 (14)	0.00786 (16)	−0.00082 (13)
O1	0.0222 (9)	0.0246 (9)	0.0173 (9)	−0.0072 (7)	0.0087 (8)	0.0028 (7)
O2	0.0254 (10)	0.0302 (10)	0.0190 (9)	0.0122 (8)	0.0101 (8)	−0.0010 (7)
O3	0.0242 (9)	0.0174 (9)	0.0133 (8)	−0.0004 (7)	0.0110 (7)	0.0004 (6)
O4	0.0140 (8)	0.0178 (9)	0.0118 (8)	−0.0018 (6)	0.0074 (7)	−0.0005 (6)
O5	0.0264 (10)	0.0203 (9)	0.0237 (10)	0.0048 (7)	0.0189 (8)	0.0033 (7)
O6	0.0422 (12)	0.0414 (12)	0.0202 (10)	−0.0249 (10)	0.0176 (9)	−0.0157 (8)
O7	0.0315 (11)	0.0282 (10)	0.0198 (9)	0.0136 (8)	0.0143 (8)	0.0090 (7)
Cr3	0.0135 (2)	0.0144 (2)	0.01207 (19)	−0.00019 (14)	0.00655 (16)	0.00043 (14)
Cr4	0.0156 (2)	0.0147 (2)	0.01179 (19)	0.00095 (14)	0.00741 (16)	−0.00091 (13)
O8	0.0246 (10)	0.0328 (11)	0.0250 (10)	−0.0072 (8)	0.0095 (8)	0.0110 (8)
O9	0.0253 (10)	0.0289 (10)	0.0210 (9)	0.0056 (8)	0.0101 (8)	−0.0072 (8)
O10	0.0162 (9)	0.0168 (9)	0.0233 (9)	−0.0012 (6)	0.0097 (8)	−0.0010 (7)
O11	0.0169 (9)	0.0228 (9)	0.0128 (8)	0.0018 (7)	0.0063 (7)	−0.0024 (7)
O12	0.0348 (12)	0.0212 (10)	0.0418 (12)	0.0093 (8)	0.0213 (10)	0.0123 (8)
O13	0.0224 (10)	0.0478 (13)	0.0247 (10)	0.0023 (9)	0.0072 (8)	−0.0187 (9)
O14	0.0280 (10)	0.0314 (10)	0.0237 (10)	−0.0016 (8)	0.0164 (9)	0.0043 (8)
N1	0.0185 (11)	0.0118 (10)	0.0255 (12)	−0.0007 (8)	0.0046 (9)	−0.0024 (8)
C1	0.0188 (13)	0.0218 (13)	0.0200 (13)	0.0039 (10)	0.0074 (11)	−0.0039 (10)
C2	0.0185 (13)	0.0184 (12)	0.0194 (13)	0.0039 (10)	0.0113 (11)	0.0036 (10)
C3	0.0121 (11)	0.0141 (11)	0.0191 (12)	0.0003 (9)	0.0065 (10)	0.0010 (9)
C4	0.0164 (12)	0.0219 (13)	0.0159 (12)	−0.0011 (10)	0.0078 (10)	0.0021 (9)
C5	0.0187 (13)	0.0189 (12)	0.0223 (13)	−0.0001 (10)	0.0072 (11)	0.0071 (10)
N2	0.0328 (13)	0.0157 (10)	0.0320 (13)	−0.0039 (9)	0.0233 (11)	−0.0041 (9)
N3	0.0219 (11)	0.0107 (10)	0.0277 (12)	−0.0011 (8)	0.0094 (10)	0.0004 (8)
C6	0.0221 (13)	0.0216 (13)	0.0225 (13)	0.0008 (10)	0.0117 (11)	−0.0039 (10)
C7	0.0244 (14)	0.0179 (12)	0.0187 (13)	−0.0006 (10)	0.0140 (11)	−0.0008 (10)
C8	0.0120 (11)	0.0162 (12)	0.0153 (12)	0.0013 (9)	0.0046 (10)	0.0000 (9)
C9	0.0173 (12)	0.0219 (12)	0.0147 (12)	0.0024 (10)	0.0085 (10)	0.0020 (9)
C10	0.0174 (13)	0.0237 (13)	0.0215 (13)	0.0008 (10)	0.0085 (11)	0.0074 (10)
N4	0.0346 (13)	0.0152 (10)	0.0272 (12)	−0.0019 (9)	0.0216 (11)	−0.0025 (9)
N5	0.0226 (12)	0.0129 (10)	0.0287 (12)	−0.0010 (9)	0.0066 (10)	0.0048 (9)
C11	0.0215 (14)	0.0286 (14)	0.0228 (14)	−0.0014 (11)	0.0105 (11)	0.0095 (11)
C12	0.0176 (13)	0.0256 (13)	0.0163 (12)	−0.0012 (10)	0.0101 (11)	−0.0011 (10)
C13	0.0137 (12)	0.0165 (12)	0.0178 (12)	−0.0004 (9)	0.0064 (10)	0.0001 (9)
C14	0.0194 (13)	0.0211 (13)	0.0171 (12)	0.0007 (10)	0.0102 (11)	0.0007 (10)
C15	0.0194 (13)	0.0176 (12)	0.0189 (13)	0.0025 (10)	0.0042 (11)	−0.0030 (10)
N6	0.0342 (13)	0.0172 (11)	0.0322 (12)	−0.0065 (9)	0.0246 (11)	−0.0050 (9)
N7	0.0203 (11)	0.0118 (10)	0.0214 (11)	0.0017 (8)	0.0072 (9)	0.0006 (8)
C16	0.0175 (13)	0.0201 (13)	0.0187 (13)	0.0008 (10)	0.0076 (10)	0.0074 (10)
C17	0.0169 (12)	0.0209 (13)	0.0173 (12)	−0.0001 (10)	0.0102 (10)	0.0009 (9)
C18	0.0114 (11)	0.0152 (11)	0.0173 (12)	0.0004 (9)	0.0067 (10)	0.0010 (9)
C19	0.0192 (13)	0.0187 (12)	0.0165 (12)	0.0018 (10)	0.0106 (10)	0.0028 (9)
C20	0.0212 (13)	0.0206 (12)	0.0169 (12)	0.0048 (10)	0.0100 (11)	−0.0010 (10)
N8	0.0312 (13)	0.0165 (10)	0.0284 (12)	−0.0045 (9)	0.0215 (11)	−0.0037 (9)

Cr1—O2	1.6158 (17)	C7—H7	0.9300
Cr1—O1	1.6178 (17)	C8—N4	1.327 (3)
Cr1—O3	1.6193 (16)	C8—C9	1.413 (3)
Cr1—O4	1.8041 (17)	C9—C10	1.361 (3)
Cr2—O6	1.6072 (18)	C9—H9	0.9300
Cr2—O7	1.6160 (17)	C10—H10	0.9300
Cr2—O5	1.6219 (18)	N4—H4A	0.8600
Cr2—O4	1.8020 (16)	N4—H4B	0.8600
Cr3—O8	1.6115 (17)	N5—C11	1.344 (3)
Cr3—O9	1.6175 (17)	N5—C15	1.347 (3)
Cr3—O10	1.6202 (17)	N5—HN5	0.8600
Cr3—O11	1.8044 (17)	C11—C12	1.360 (3)
Cr4—O13	1.6038 (17)	C11—H11	0.9300
Cr4—O12	1.6109 (18)	C12—C13	1.415 (3)
Cr4—O14	1.6188 (17)	C12—H12	0.9300
Cr4—O11	1.8059 (17)	C13—N6	1.320 (3)
N1—C1	1.345 (3)	C13—C14	1.414 (3)
N1—C5	1.348 (3)	C14—C15	1.357 (3)
N1—HN1	0.8600	C14—H14	0.9300
C1—C2	1.356 (3)	C15—H15	0.9300
C1—H1	0.9300	N6—H6A	0.8600
C2—C3	1.419 (3)	N6—H6B	0.8600
C2—H2	0.9300	N7—C16	1.347 (3)
C3—N2	1.322 (3)	N7—C20	1.351 (3)
C3—C4	1.415 (3)	N7—HN7	0.8600
C4—C5	1.355 (3)	C16—C17	1.362 (3)
C4—H4	0.9300	C16—H16	0.9300
C5—H5	0.9300	C17—C18	1.412 (3)
N2—H2A	0.8600	C17—H17	0.9300
N2—H2B	0.8600	C18—N8	1.322 (3)
N3—C10	1.341 (3)	C18—C19	1.419 (3)
N3—C6	1.350 (3)	C19—C20	1.357 (3)
N3—HN3	0.8600	C19—H19	0.9300
C6—C7	1.360 (3)	C20—H20	0.9300
C6—H6	0.9300	N8—H8A	0.8600
C7—C8	1.413 (3)	N8—H8B	0.8600
O2—Cr1—O1	111.77 (10)	C8—C7—H7	119.8
O2—Cr1—O3	109.52 (8)	N4—C8—C7	120.9 (2)
O1—Cr1—O3	110.20 (8)	N4—C8—C9	121.9 (2)
O2—Cr1—O4	109.46 (8)	C7—C8—C9	117.2 (2)
O1—Cr1—O4	108.93 (8)	C10—C9—C8	119.7 (2)
O3—Cr1—O4	106.84 (8)	C10—C9—H9	120.1
O6—Cr2—O7	111.36 (10)	C8—C9—H9	120.1
O6—Cr2—O5	111.31 (9)	N3—C10—C9	121.0 (2)
O7—Cr2—O5	109.97 (9)	N3—C10—H10	119.5
O6—Cr2—O4	107.12 (8)	C9—C10—H10	119.5
O7—Cr2—O4	108.44 (8)	C8—N4—H4A	120.0
O5—Cr2—O4	108.51 (8)	C8—N4—H4B	120.0
O8—Cr3—O9	110.98 (11)	H4A—N4—H4B	120.0
O8—Cr3—O10	110.71 (9)	C11—N5—C15	121.0 (2)
O9—Cr3—O10	110.95 (9)	C11—N5—HN5	119.5
O8—Cr3—O11	109.70 (9)	C15—N5—HN5	119.5
O9—Cr3—O11	108.91 (8)	N5—C11—C12	121.2 (2)
O10—Cr3—O11	105.42 (8)	N5—C11—H11	119.4
O13—Cr4—O12	110.61 (10)	C12—C11—H11	119.4
O13—Cr4—O14	112.22 (10)	C11—C12—C13	119.8 (2)
O12—Cr4—O14	110.18 (9)	C11—C12—H12	120.1
O13—Cr4—O11	105.75 (8)	C13—C12—H12	120.1
O12—Cr4—O11	107.90 (9)	N6—C13—C14	121.7 (2)
O14—Cr4—O11	110.01 (9)	N6—C13—C12	121.3 (2)
Cr2—O4—Cr1	120.12 (9)	C14—C13—C12	116.9 (2)
Cr3—O11—Cr4	125.63 (9)	C15—C14—C13	120.3 (2)
C1—N1—C5	121.1 (2)	C15—C14—H14	119.8
C1—N1—HN1	119.5	C13—C14—H14	119.8
C5—N1—HN1	119.5	N5—C15—C14	120.8 (2)
N1—C1—C2	121.1 (2)	N5—C15—H15	119.6
N1—C1—H1	119.4	C14—C15—H15	119.6
C2—C1—H1	119.4	C13—N6—H6A	120.0
C1—C2—C3	119.8 (2)	C13—N6—H6B	120.0
C1—C2—H2	120.1	H6A—N6—H6B	120.0
C3—C2—H2	120.1	C16—N7—C20	121.3 (2)
N2—C3—C4	121.5 (2)	C16—N7—HN7	119.4
N2—C3—C2	121.4 (2)	C20—N7—HN7	119.4
C4—C3—C2	117.1 (2)	N7—C16—C17	120.5 (2)
C5—C4—C3	120.1 (2)	N7—C16—H16	119.7
C5—C4—H4	120.0	C17—C16—H16	119.7
C3—C4—H4	120.0	C16—C17—C18	120.2 (2)
N1—C5—C4	120.9 (2)	C16—C17—H17	119.9
N1—C5—H5	119.6	C18—C17—H17	119.9
C4—C5—H5	119.6	N8—C18—C17	121.5 (2)
C3—N2—H2A	120.0	N8—C18—C19	121.3 (2)
C3—N2—H2B	120.0	C17—C18—C19	117.2 (2)
H2A—N2—H2B	120.0	C20—C19—C18	119.8 (2)
C10—N3—C6	121.6 (2)	C20—C19—H19	120.1
C10—N3—HN3	119.2	C18—C19—H19	120.1
C6—N3—HN3	119.2	N7—C20—C19	121.0 (2)
N3—C6—C7	120.1 (2)	N7—C20—H20	119.5
N3—C6—H6	119.9	C19—C20—H20	119.5
C7—C6—H6	119.9	C18—N8—H8A	120.0
C6—C7—C8	120.4 (2)	C18—N8—H8B	120.0
C6—C7—H7	119.8	H8A—N8—H8B	120.0

D—H···A	D—H	H···A	D···A	D—H···A
N1—HN1···O10i	0.86	2.13	2.842 (3)	140
N1—HN1···O4ii	0.86	2.42	3.065 (2)	133
N2—H2A···O9iii	0.86	2.19	3.022 (3)	162
N2—H2B···O11iv	0.86	2.13	2.978 (3)	167
N3—HN3···O5v	0.86	2.14	2.871 (3)	142
N3—HN3···O3ii	0.86	2.36	3.003 (3)	132
N4—H4A···O13iv	0.86	2.32	3.067 (3)	145
N4—H4A···O1iii	0.86	2.43	3.042 (3)	128
N4—H4B···O14iii	0.86	2.14	2.965 (3)	160
N5—HN5···O5iii	0.86	2.11	2.890 (3)	151
N5—HN5···O3vi	0.86	2.48	3.094 (3)	129
N6—H6A···O2v	0.86	2.45	2.998 (3)	122
N6—H6B···O14v	0.86	2.10	2.923 (3)	160
N7—HN7···O10vii	0.86	2.26	2.900 (3)	131
N7—HN7···O4vi	0.86	2.22	2.927 (2)	139
N8—H8A···O8v	0.86	2.31	3.121 (3)	156
N8—H8B···O11	0.86	2.17	3.033 (3)	176
C1—H1···O7ii	0.93	2.43	3.305 (3)	156
C5—H5···O6v	0.93	2.28	3.192 (3)	165
C6—H6···O1ii	0.93	2.31	3.204 (3)	161
C9—H9···O12iii	0.93	2.47	3.359 (3)	161
C10—H10···O2v	0.93	2.40	3.209 (3)	145
C11—H11···O1iii	0.93	2.41	3.205 (3)	144
C14—H14···O12	0.93	2.46	3.248 (3)	143
C15—H15···O2vi	0.93	2.32	3.244 (3)	171
C16—H16···O7iii	0.93	2.37	3.197 (3)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—HN1⋯O10i	0.86	2.13	2.842 (3)	140
N2—H2A⋯O9ii	0.86	2.19	3.022 (3)	162
N2—H2B⋯O11iii	0.86	2.13	2.978 (3)	167
N3—HN3⋯O5iv	0.86	2.14	2.871 (3)	142
N4—H4A⋯O13iii	0.86	2.32	3.067 (3)	145
N4—H4B⋯O14ii	0.86	2.14	2.965 (3)	160
N5—HN5⋯O5ii	0.86	2.11	2.890 (3)	151
N6—H6A⋯O2iv	0.86	2.45	2.998 (3)	122
N6—H6B⋯O14iv	0.86	2.10	2.923 (3)	160
N7—HN7⋯O4v	0.86	2.22	2.927 (2)	139
N8—H8A⋯O8iv	0.86	2.31	3.121 (3)	156
N8—H8B⋯O11	0.86	2.17	3.033 (3)	176
C1—H1⋯O7vi	0.93	2.43	3.305 (3)	156
C5—H5⋯O6iv	0.93	2.28	3.192 (3)	165
C6—H6⋯O1vi	0.93	2.31	3.204 (3)	161
C9—H9⋯O12ii	0.93	2.47	3.359 (3)	161
C10—H10⋯O2iv	0.93	2.40	3.209 (3)	145
C11—H11⋯O1ii	0.93	2.41	3.205 (3)	144
C14—H14⋯O12	0.93	2.46	3.248 (3)	143
C15—H15⋯O2v	0.93	2.32	3.244 (3)	171
C16—H16⋯O7ii	0.93	2.37	3.197 (3)	148

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