Bis(4,4'-bipyridinium) di-μ-hydroxido-bis-[dihydroxido(pyridine-2,6-dicarboxyl-ato)anti-monate(III,V)] octa-hydrate.

The reaction of anti-mony(III) chloride, 4,4'-bipyridine (4,4'-bipy) and pyridine-2,6-dicarboxylic acid (pydcH(2)), in a 1:2:2 molar ratio in an aqueous solution, resulted in the formation of the title centrosymmetric disordered mixed-valence Sb(III)/Sb(V) compound, (C(10)H(9)N(2))(2)[Sb(2)(C(7)H(3)NO(4))(2)(OH)(6)]·8H(2)O or (4,4'-bipyH)(2)[Sb(pydc)(OH)(2)(μ-OH)](2)·8H(2)O. The seven donor atoms of the (pydc)(2-) groups and the hydroxido ligands form a distorted penta-gonal-bipyramidal arrangement around the Sb(III)/Sb(V) centers. C-H⋯π stacking inter-actions between CH groups of the complex dianion and the aromatic rings of the (4,4'-bipyH)(+) cations, with a distance of 2.89 Å, are observed. In the crystal structure, a wide range of noncovalent inter-actions, consisting of O-H⋯O, N-H⋯O and C-H⋯O hydrogen bonds [D⋯A ranging from 2.722 (2) to 3.137 (3) Å], ion pairing, π-π stacking [centroid-centroid distance of 3.4363 (13) Å] and C-H⋯π inter-actions, connect the various components into a supra-molecular structure.

Related literature

For related literature, see: Aghabozorg, Attar Gharamaleki, Ghadermazi et al. (2007 ▶); Aghabozorg, Attar Gharamaleki, Ghasemikhah et al. (2007 ▶); Aghabozorg, Daneshvar et al. (2007 ▶).

Experimental

Crystal data

(C10H9N2)2[Sb2(C7H3NO4)2(OH)6]·8H2O

M = 1134.27

Triclinic,

a = 10.0149 (11) Å

b = 10.4826 (12) Å

c = 11.0974 (12) Å

α = 92.816 (2)°

β = 97.813 (2)°

γ = 114.046 (2)°

V = 1047.0 (2) Å3

Z = 1

Mo Kα radiation

μ = 1.38 mm−1

T = 150 (2) K

0.43 × 0.41 × 0.39 mm

Data collection

Bruker SMART 1000 diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.588, T max = 0.614 (expected range = 0.557–0.583)

12026 measured reflections

4790 independent reflections

4536 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.023

wR(F 2) = 0.060

S = 1.07

4790 reflections

289 parameters

H-atom parameters constrained

Δρmax = 0.91 e Å−3

Δρmin = −0.70 e Å−3

Data collection: SMART (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808001372/su2034sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808001372/su2034Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

(C10H9N2)2[Sb2(C7H3NO4)2(OH)6]·8H2O	Z = 1
Mr = 1134.27	F000 = 570
Triclinic, P1	Dx = 1.799 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 10.0149 (11) Å	Cell parameters from 9637 reflections
b = 10.4826 (12) Å	θ = 2.3–28.5º
c = 11.0974 (12) Å	µ = 1.38 mm−1
α = 92.816 (2)º	T = 150 (2) K
β = 97.813 (2)º	Block, colourless
γ = 114.046 (2)º	0.43 × 0.41 × 0.39 mm
V = 1047.0 (2) Å3

Bruker SMART 1000 diffractometer	4790 independent reflections
Radiation source: fine-focus sealed tube	4536 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.022
Detector resolution: 100 pixels mm-1	θmax = 28.6º
T = 150(2) K	θmin = 1.9º
ω scans	h = −13→13
Absorption correction: multi-scan(SADABS; Bruker, 2004)	k = −13→14
Tmin = 0.588, Tmax = 0.614	l = −14→14
12026 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.023	H-atom parameters constrained
wR(F2) = 0.060	w = 1/[σ2(Fo2) + (0.0357P)2 + 0.4561P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.001
4790 reflections	Δρmax = 0.91 e Å−3
289 parameters	Δρmin = −0.70 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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.

	x	y	z	Uiso*/Ueq
Sb1	0.140841 (13)	0.156744 (12)	0.066281 (11)	0.01594 (5)
O1	0.26613 (19)	0.54127 (16)	−0.09185 (15)	0.0316 (4)
O2	0.18376 (16)	0.31302 (14)	−0.06761 (13)	0.0199 (3)
O3	0.23282 (16)	0.13870 (15)	0.26029 (13)	0.0199 (3)
O4	0.40060 (16)	0.23914 (16)	0.43165 (13)	0.0250 (3)
O5	0.00823 (16)	0.23727 (15)	0.12176 (13)	0.0195 (3)
H5A	−0.0555	0.1808	0.1595	0.023*
O6	0.29732 (15)	0.09324 (15)	0.02785 (13)	0.0191 (3)
H6A	0.2826	0.0571	−0.0457	0.023*
O7	−0.00038 (15)	0.04568 (14)	−0.09706 (12)	0.0176 (3)
H7A	0.0135	0.0703	−0.1678	0.021*
O8	0.02690 (17)	0.10749 (16)	0.66612 (14)	0.0263 (3)
H8B	−0.0591	0.0577	0.6255	0.032*
H8A	0.0522	0.1931	0.6543	0.032*
O9	0.57770 (18)	0.19751 (17)	0.16030 (17)	0.0339 (4)
H9A	0.6340	0.2752	0.1385	0.041*
H9B	0.4909	0.1677	0.1186	0.041*
O10	0.73724 (19)	0.04248 (19)	0.20370 (16)	0.0325 (4)
H10A	0.7380	0.0232	0.2772	0.039*
H10B	0.6871	0.0909	0.1924	0.039*
O11	0.21742 (19)	0.02296 (18)	0.55043 (16)	0.0336 (4)
H11A	0.2735	0.0927	0.5183	0.040*
H11B	0.1591	0.0538	0.5768	0.040*
N1	0.32909 (17)	0.36461 (17)	0.15357 (15)	0.0165 (3)
N2	0.1174 (2)	0.3633 (2)	0.57504 (17)	0.0255 (4)
N3	0.2738 (2)	0.87729 (19)	0.16815 (17)	0.0246 (4)
H3A	0.2886	0.9474	0.1279	0.030*
C1	0.2631 (2)	0.4435 (2)	−0.03335 (18)	0.0193 (4)
C2	0.3588 (2)	0.4768 (2)	0.09189 (18)	0.0176 (4)
C3	0.4662 (2)	0.6083 (2)	0.14286 (19)	0.0214 (4)
H3	0.4875	0.6873	0.0982	0.026*
C4	0.5418 (2)	0.6217 (2)	0.2608 (2)	0.0231 (4)
H4	0.6172	0.7101	0.2973	0.028*
C5	0.5066 (2)	0.5052 (2)	0.32512 (19)	0.0205 (4)
H5	0.5555	0.5131	0.4065	0.025*
C6	0.3983 (2)	0.3768 (2)	0.26789 (18)	0.0171 (4)
C7	0.3418 (2)	0.2413 (2)	0.32655 (18)	0.0188 (4)
C8	0.3600 (2)	0.9113 (2)	0.2791 (2)	0.0252 (4)
H8	0.4367	1.0033	0.3014	0.030*
C9	0.3369 (2)	0.8123 (2)	0.3604 (2)	0.0233 (4)
H9	0.3985	0.8354	0.4384	0.028*
C10	0.2220 (2)	0.6773 (2)	0.32763 (19)	0.0194 (4)
C11	0.1893 (2)	0.5700 (2)	0.41423 (18)	0.0192 (4)
C12	0.2114 (2)	0.6064 (2)	0.54032 (19)	0.0224 (4)
H12	0.2522	0.7023	0.5737	0.027*
C13	0.1729 (2)	0.5006 (2)	0.6161 (2)	0.0256 (4)
H13	0.1864	0.5265	0.7016	0.031*
C14	0.0983 (2)	0.3295 (2)	0.4541 (2)	0.0255 (4)
H14	0.0601	0.2328	0.4238	0.031*
C15	0.1307 (2)	0.4270 (2)	0.37092 (19)	0.0217 (4)
H15	0.1136	0.3975	0.2857	0.026*
C16	0.1364 (2)	0.6464 (2)	0.2104 (2)	0.0230 (4)
H16	0.0589	0.5554	0.1853	0.028*
C17	0.1649 (2)	0.7487 (2)	0.1313 (2)	0.0247 (4)
H17	0.1079	0.7280	0.0514	0.030*

	U11	U22	U33	U12	U13	U23
Sb1	0.01651 (7)	0.01415 (7)	0.01362 (8)	0.00330 (5)	0.00071 (5)	0.00303 (5)
O1	0.0417 (9)	0.0180 (7)	0.0228 (8)	0.0030 (7)	−0.0058 (7)	0.0079 (6)
O2	0.0222 (7)	0.0156 (7)	0.0143 (7)	0.0012 (5)	−0.0006 (5)	0.0033 (5)
O3	0.0210 (7)	0.0179 (7)	0.0153 (7)	0.0035 (6)	−0.0007 (5)	0.0038 (5)
O4	0.0247 (7)	0.0272 (8)	0.0156 (7)	0.0050 (6)	−0.0027 (6)	0.0058 (6)
O5	0.0202 (7)	0.0199 (7)	0.0182 (7)	0.0080 (6)	0.0043 (5)	0.0032 (5)
O6	0.0186 (7)	0.0202 (7)	0.0172 (7)	0.0071 (6)	0.0022 (5)	0.0029 (5)
O7	0.0198 (6)	0.0148 (6)	0.0121 (6)	0.0012 (5)	0.0013 (5)	0.0049 (5)
O8	0.0286 (8)	0.0218 (7)	0.0206 (8)	0.0030 (6)	0.0021 (6)	0.0059 (6)
O9	0.0229 (8)	0.0237 (8)	0.0488 (11)	0.0052 (6)	−0.0033 (7)	0.0142 (7)
O10	0.0406 (9)	0.0425 (10)	0.0260 (8)	0.0269 (8)	0.0108 (7)	0.0095 (7)
O11	0.0363 (9)	0.0283 (9)	0.0356 (10)	0.0106 (7)	0.0111 (8)	0.0107 (7)
N1	0.0159 (7)	0.0166 (8)	0.0148 (8)	0.0047 (6)	0.0019 (6)	0.0021 (6)
N2	0.0231 (9)	0.0313 (10)	0.0240 (9)	0.0120 (8)	0.0047 (7)	0.0123 (8)
N3	0.0276 (9)	0.0237 (9)	0.0262 (10)	0.0129 (7)	0.0063 (7)	0.0108 (7)
C1	0.0199 (9)	0.0178 (9)	0.0163 (9)	0.0040 (7)	0.0018 (7)	0.0039 (7)
C2	0.0180 (9)	0.0169 (9)	0.0149 (9)	0.0047 (7)	0.0016 (7)	0.0021 (7)
C3	0.0221 (9)	0.0172 (9)	0.0211 (10)	0.0048 (8)	0.0021 (8)	0.0019 (8)
C4	0.0191 (9)	0.0184 (10)	0.0245 (11)	0.0023 (8)	0.0006 (8)	−0.0034 (8)
C5	0.0168 (9)	0.0242 (10)	0.0160 (9)	0.0054 (8)	−0.0008 (7)	−0.0010 (8)
C6	0.0151 (8)	0.0203 (9)	0.0150 (9)	0.0068 (7)	0.0018 (7)	0.0017 (7)
C7	0.0189 (9)	0.0193 (9)	0.0167 (9)	0.0062 (7)	0.0032 (7)	0.0028 (7)
C8	0.0248 (10)	0.0213 (10)	0.0281 (11)	0.0084 (8)	0.0033 (9)	0.0049 (9)
C9	0.0233 (10)	0.0229 (10)	0.0223 (10)	0.0093 (8)	0.0005 (8)	0.0037 (8)
C10	0.0201 (9)	0.0212 (10)	0.0185 (10)	0.0099 (8)	0.0036 (7)	0.0036 (8)
C11	0.0184 (9)	0.0233 (10)	0.0173 (9)	0.0099 (8)	0.0026 (7)	0.0046 (8)
C12	0.0204 (10)	0.0244 (10)	0.0184 (10)	0.0069 (8)	−0.0010 (8)	0.0003 (8)
C13	0.0224 (10)	0.0367 (12)	0.0170 (10)	0.0119 (9)	0.0016 (8)	0.0063 (9)
C14	0.0270 (10)	0.0224 (10)	0.0293 (12)	0.0115 (9)	0.0066 (9)	0.0072 (9)
C15	0.0247 (10)	0.0236 (10)	0.0180 (10)	0.0114 (8)	0.0037 (8)	0.0029 (8)
C16	0.0222 (10)	0.0240 (10)	0.0210 (10)	0.0084 (8)	0.0012 (8)	0.0043 (8)
C17	0.0252 (10)	0.0303 (11)	0.0195 (10)	0.0128 (9)	0.0013 (8)	0.0070 (9)

Sb1—O5	1.9850 (14)	N3—C8	1.343 (3)
Sb1—O6	2.0211 (14)	N3—H3A	0.8500
Sb1—O7i	2.0898 (13)	C1—C2	1.513 (3)
Sb1—O7	2.0964 (13)	C2—C3	1.389 (3)
Sb1—O2	2.2169 (14)	C3—C4	1.390 (3)
Sb1—O3	2.2721 (14)	C3—H3	0.9500
Sb1—N1	2.2779 (16)	C4—C5	1.389 (3)
O1—C1	1.232 (3)	C4—H4	0.9500
O2—C1	1.276 (2)	C5—C6	1.390 (3)
O3—C7	1.279 (2)	C5—H5	0.9500
O4—C7	1.239 (2)	C6—C7	1.516 (3)
O5—H5A	0.8500	C8—C9	1.378 (3)
O6—H6A	0.8499	C8—H8	0.9500
O7—Sb1i	2.0898 (13)	C9—C10	1.403 (3)
O7—H7A	0.8499	C9—H9	0.9500
O8—H8B	0.8501	C10—C16	1.400 (3)
O8—H8A	0.8499	C10—C11	1.479 (3)
O9—H9A	0.8500	C11—C12	1.395 (3)
O9—H9B	0.8500	C11—C15	1.400 (3)
O10—H10A	0.8500	C12—C13	1.385 (3)
O10—H10B	0.8499	C12—H12	0.9500
O11—H11A	0.8501	C13—H13	0.9500
O11—H11B	0.8500	C14—C15	1.380 (3)
N1—C6	1.334 (3)	C14—H14	0.9500
N1—C2	1.337 (2)	C15—H15	0.9500
N2—C14	1.338 (3)	C16—C17	1.383 (3)
N2—C13	1.343 (3)	C16—H16	0.9500
N3—C17	1.342 (3)	C17—H17	0.9500
O5—Sb1—O6	172.26 (6)	C2—C3—C4	118.43 (19)
O5—Sb1—O7i	92.04 (6)	C2—C3—H3	120.8
O6—Sb1—O7i	92.06 (6)	C4—C3—H3	120.8
O5—Sb1—O7	96.38 (6)	C5—C4—C3	119.68 (19)
O6—Sb1—O7	91.19 (6)	C5—C4—H4	120.2
O7i—Sb1—O7	69.97 (6)	C3—C4—H4	120.2
O5—Sb1—O2	85.52 (6)	C4—C5—C6	118.62 (19)
O6—Sb1—O2	94.93 (6)	C4—C5—H5	120.7
O7i—Sb1—O2	144.33 (5)	C6—C5—H5	120.7
O7—Sb1—O2	74.95 (5)	N1—C6—C5	121.11 (18)
O5—Sb1—O3	93.16 (6)	N1—C6—C7	113.42 (17)
O6—Sb1—O3	81.44 (6)	C5—C6—C7	125.42 (18)
O7i—Sb1—O3	76.29 (5)	O4—C7—O3	126.20 (19)
O7—Sb1—O3	145.17 (5)	O4—C7—C6	119.09 (18)
O2—Sb1—O3	139.34 (5)	O3—C7—C6	114.70 (17)
O5—Sb1—N1	85.26 (6)	N3—C8—C9	119.8 (2)
O6—Sb1—N1	87.62 (6)	N3—C8—H8	120.1
O7i—Sb1—N1	145.09 (6)	C9—C8—H8	120.1
O7—Sb1—N1	144.94 (5)	C8—C9—C10	119.8 (2)
O2—Sb1—N1	70.26 (6)	C8—C9—H9	120.1
O3—Sb1—N1	69.14 (5)	C10—C9—H9	120.1
C1—O2—Sb1	120.96 (12)	C16—C10—C9	118.21 (19)
C7—O3—Sb1	122.17 (13)	C16—C10—C11	120.30 (18)
Sb1—O5—H5A	112.1	C9—C10—C11	121.48 (18)
Sb1—O6—H6A	114.1	C12—C11—C15	117.78 (19)
Sb1i—O7—Sb1	110.03 (6)	C12—C11—C10	121.82 (19)
Sb1i—O7—H7A	123.7	C15—C11—C10	120.38 (18)
Sb1—O7—H7A	124.2	C13—C12—C11	119.0 (2)
H8B—O8—H8A	109.6	C13—C12—H12	120.5
H9A—O9—H9B	110.3	C11—C12—H12	120.5
H10A—O10—H10B	107.5	N2—C13—C12	123.4 (2)
H11A—O11—H11B	102.1	N2—C13—H13	118.3
C6—N1—C2	120.88 (17)	C12—C13—H13	118.3
C6—N1—Sb1	120.49 (13)	N2—C14—C15	123.8 (2)
C2—N1—Sb1	118.34 (13)	N2—C14—H14	118.1
C14—N2—C13	117.14 (19)	C15—C14—H14	118.1
C17—N3—C8	122.71 (19)	C14—C15—C11	118.8 (2)
C17—N3—H3A	123.8	C14—C15—H15	120.6
C8—N3—H3A	113.1	C11—C15—H15	120.6
O1—C1—O2	125.97 (19)	C17—C16—C10	119.9 (2)
O1—C1—C2	118.90 (18)	C17—C16—H16	120.1
O2—C1—C2	115.12 (17)	C10—C16—H16	120.1
N1—C2—C3	121.23 (18)	N3—C17—C16	119.6 (2)
N1—C2—C1	113.09 (17)	N3—C17—H17	120.2
C3—C2—C1	125.67 (18)	C16—C17—H17	120.2
O5—Sb1—O2—C1	72.72 (15)	O1—C1—C2—C3	−8.7 (3)
O6—Sb1—O2—C1	−99.53 (16)	O2—C1—C2—C3	172.2 (2)
O7i—Sb1—O2—C1	159.97 (14)	N1—C2—C3—C4	−0.7 (3)
O7—Sb1—O2—C1	170.56 (16)	C1—C2—C3—C4	178.22 (19)
O3—Sb1—O2—C1	−16.93 (19)	C2—C3—C4—C5	−1.2 (3)
N1—Sb1—O2—C1	−13.85 (15)	C3—C4—C5—C6	1.6 (3)
O5—Sb1—O3—C7	−85.43 (15)	C2—N1—C6—C5	−2.0 (3)
O6—Sb1—O3—C7	88.99 (15)	Sb1—N1—C6—C5	−175.71 (14)
O7i—Sb1—O3—C7	−176.76 (16)	C2—N1—C6—C7	175.42 (17)
O7—Sb1—O3—C7	168.65 (14)	Sb1—N1—C6—C7	1.7 (2)
O2—Sb1—O3—C7	1.37 (19)	C4—C5—C6—N1	0.0 (3)
N1—Sb1—O3—C7	−1.72 (15)	C4—C5—C6—C7	−177.06 (19)
O5—Sb1—O7—Sb1i	−89.85 (7)	Sb1—O3—C7—O4	−178.17 (16)
O6—Sb1—O7—Sb1i	91.76 (7)	Sb1—O3—C7—C6	3.1 (2)
O7i—Sb1—O7—Sb1i	0.0	N1—C6—C7—O4	178.14 (18)
O2—Sb1—O7—Sb1i	−173.45 (8)	C5—C6—C7—O4	−4.6 (3)
O3—Sb1—O7—Sb1i	15.10 (13)	N1—C6—C7—O3	−3.1 (3)
N1—Sb1—O7—Sb1i	179.31 (7)	C5—C6—C7—O3	174.24 (19)
O5—Sb1—N1—C6	94.99 (15)	C17—N3—C8—C9	−0.7 (3)
O6—Sb1—N1—C6	−81.97 (15)	N3—C8—C9—C10	−1.0 (3)
O7i—Sb1—N1—C6	8.2 (2)	C8—C9—C10—C16	1.8 (3)
O7—Sb1—N1—C6	−170.64 (13)	C8—C9—C10—C11	−177.30 (19)
O2—Sb1—N1—C6	−178.07 (16)	C16—C10—C11—C12	−147.0 (2)
O3—Sb1—N1—C6	−0.22 (14)	C9—C10—C11—C12	32.1 (3)
O5—Sb1—N1—C2	−78.87 (15)	C16—C10—C11—C15	31.2 (3)
O6—Sb1—N1—C2	104.17 (15)	C9—C10—C11—C15	−149.8 (2)
O7i—Sb1—N1—C2	−165.64 (13)	C15—C11—C12—C13	−0.9 (3)
O7—Sb1—N1—C2	15.5 (2)	C10—C11—C12—C13	177.34 (19)
O2—Sb1—N1—C2	8.06 (14)	C14—N2—C13—C12	−0.6 (3)
O3—Sb1—N1—C2	−174.08 (16)	C11—C12—C13—N2	1.3 (3)
Sb1—O2—C1—O1	−161.95 (18)	C13—N2—C14—C15	−0.6 (3)
Sb1—O2—C1—C2	17.1 (2)	N2—C14—C15—C11	1.0 (3)
C6—N1—C2—C3	2.3 (3)	C12—C11—C15—C14	−0.2 (3)
Sb1—N1—C2—C3	176.18 (15)	C10—C11—C15—C14	−178.46 (19)
C6—N1—C2—C1	−176.70 (17)	C9—C10—C16—C17	−1.0 (3)
Sb1—N1—C2—C1	−2.9 (2)	C11—C10—C16—C17	178.12 (19)
O1—C1—C2—N1	170.32 (19)	C8—N3—C17—C16	1.5 (3)
O2—C1—C2—N1	−8.8 (3)	C10—C16—C17—N3	−0.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O10ii	0.85	2.13	2.949 (2)	161
O6—H6A···O10iii	0.85	1.94	2.783 (2)	172
O7—H7A···O8iv	0.85	1.91	2.760 (2)	174
O8—H8B···O11v	0.85	2.22	2.997 (2)	151
O8—H8B···O3v	0.85	2.61	3.067 (2)	115
O8—H8A···N2	0.85	1.93	2.751 (2)	161
O9—H9A···O1vi	0.85	1.91	2.749 (2)	170
O9—H9B···O6	0.85	1.88	2.731 (2)	177
O10—H10A···O11vii	0.85	2.03	2.867 (2)	168
O10—H10B···O9	0.85	1.87	2.722 (2)	178
O11—H11A···O4	0.85	1.95	2.793 (2)	174
O11—H11B···O8	0.85	1.99	2.830 (2)	169
N3—H3A···O6viii	0.85	1.91	2.760 (2)	173
C13—H13···O1ix	0.95	2.30	3.205 (3)	160
C15—H15···O5	0.95	2.23	3.107 (3)	153
C17—H17···O5x	0.95	2.23	3.137 (3)	159
C5—H5···Cg1(N2/C11-C15)xi	0.95	2.89	3.596 (2)	132

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5A⋯O10i	0.85	2.13	2.949 (2)	161
O6—H6A⋯O10ii	0.85	1.94	2.783 (2)	172
O7—H7A⋯O8iii	0.85	1.91	2.760 (2)	174
O8—H8B⋯O11iv	0.85	2.22	2.997 (2)	151
O8—H8B⋯O3iv	0.85	2.61	3.067 (2)	115
O8—H8A⋯N2	0.85	1.93	2.751 (2)	161
O9—H9A⋯O1v	0.85	1.91	2.749 (2)	170
O9—H9B⋯O6	0.85	1.88	2.731 (2)	177
O10—H10A⋯O11vi	0.85	2.03	2.867 (2)	168
O10—H10B⋯O9	0.85	1.87	2.722 (2)	178
O11—H11A⋯O4	0.85	1.95	2.793 (2)	174
O11—H11B⋯O8	0.85	1.99	2.830 (2)	169
N3—H3A⋯O6vii	0.85	1.91	2.760 (2)	173
C13—H13⋯O1viii	0.95	2.30	3.205 (3)	160
C15—H15⋯O5	0.95	2.23	3.107 (3)	153
C17—H17⋯O5ix	0.95	2.23	3.137 (3)	159
C5—H5⋯Cg1(N2/C11–C15)x	0.95	2.89	3.596 (2)	132

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