Benzene-1,3,5-tri-carb-oxy-lic acid-pyridinium-2-olate (1/3).

The asymmetric unit of the title compound, C9H6O6·3C5H5NO, contains one benzene-1,3,5-tri-carb-oxy-lic acid mol-ecule (BTA) and three pyridin-2-ol mol-ecules each present in the zwitterion form. In the crystal, these entities are linked through O-H⋯O(-) and N(+)-H⋯O(-) hydrogen bonds, forming sheets parallel to (10-1). These layers contain macrocyclic rings of composition [BTA]2[pyol]6 and with graph-set notation R (6) 8(44), which are stacked along c through π-π inter-actions [inter-centroid distances = 3.536 (2)-3.948 (3) Å]. They are inter-connected by N(+)-H⋯O(-) hydrogen-bonded chains of pyridin-2-ol mol-ecules running parallel to c, forming a three-dimensional network. There are also C-H⋯O hydrogen bonds present which reinforce the three-dimensional structure.

Related literature

For reports on supra­molecular crystal engineering and potential applications of co-crystals, see: Desiraju (1995 ▶); Karki et al. (2009 ▶); Aakeröy et al. (2010 ▶); Yan et al. (2012 ▶); Li et al. (2014 ▶); Ebenezer & Mu­thiah (2012 ▶. For background to related crystal structures, see: Bhogala et al. (2005 ▶); Shattock et al. (2008 ▶); Yu (2012 ▶).

Experimental

Crystal data

C9H6O6·3C5H5NO

M = 495.44

Monoclinic,

a = 14.344 (2) Å

b = 25.993 (5) Å

c = 6.7047 (10) Å

β = 117.472 (2)°

V = 2217.8 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 100 K

0.49 × 0.41 × 0.34 mm

Data collection

Bruker APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.95, T max = 0.96

12173 measured reflections

2433 independent reflections

2354 reflections with I > 2σ(I)

R int = 0.076

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.104

S = 1.08

2433 reflections

343 parameters

8 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.33 e Å−3

Δρmin = −0.25 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT-Plus-NT (Bruker 2001 ▶); data reduction: SAINT-Plus-NT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536814005534/su2712sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814005534/su2712Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814005534/su2712Isup3.cml

CCDC reference: 991203

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

C9H6O6·3C5H5NO	F(000) = 1032
Mr = 495.44	Dx = 1.484 Mg m−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 4866 reflections
a = 14.344 (2) Å	θ = 2.8–28.5°
b = 25.993 (5) Å	µ = 0.12 mm−1
c = 6.7047 (10) Å	T = 100 K
β = 117.472 (2)°	Rectangular prism, colorless
V = 2217.8 (6) Å3	0.49 × 0.41 × 0.34 mm
Z = 4

Bruker APEX CCD area-detector diffractometer	2433 independent reflections
Radiation source: fine-focus sealed tube	2354 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.076
phi and ω scans	θmax = 27.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −18→18
Tmin = 0.95, Tmax = 0.96	k = −33→32
12173 measured reflections	l = −8→8

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) = 0.104	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.0394P)2 + 2.5063P] where P = (Fo2 + 2Fc2)/3
2433 reflections	(Δ/σ)max < 0.001
343 parameters	Δρmax = 0.33 e Å−3
8 restraints	Δρmin = −0.25 e Å−3

Experimental. Spectroscopic data for the title compound: IR (KBr, cm-1): 3442, 3103, 3050, 1704, 1690, 1624, 1613, 1468, 1282, 1193, 1094, 1024.

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
N1	0.5716 (2)	0.74048 (12)	0.7948 (5)	0.0185 (7)
H1A	0.5074 (9)	0.7479 (18)	0.734 (7)	0.028*
N2	0.7381 (2)	0.23549 (13)	−0.0482 (5)	0.0212 (7)
H2A	0.6809 (18)	0.2201 (16)	−0.086 (8)	0.032*
N3	0.1812 (2)	0.06645 (12)	0.3136 (5)	0.0183 (6)
H3A	0.191 (3)	0.0665 (17)	0.199 (4)	0.027*
O1	0.0316 (2)	0.39495 (9)	0.3690 (5)	0.0200 (5)
H1'	0.031 (4)	0.3628 (2)	0.355 (8)	0.030*
O2	0.2044 (2)	0.38226 (10)	0.5822 (5)	0.0214 (6)
O3	−0.00333 (19)	0.63687 (10)	0.3527 (4)	0.0196 (6)
H3'	−0.053 (2)	0.6581 (13)	0.294 (7)	0.029*
O4	−0.11698 (19)	0.57121 (9)	0.2541 (4)	0.0164 (5)
O5	0.43466 (18)	0.53127 (10)	0.7273 (4)	0.0183 (5)
H5'	0.4927 (17)	0.5446 (16)	0.755 (8)	0.027*
O6	0.3814 (2)	0.61071 (10)	0.7524 (5)	0.0218 (6)
O7	0.8839 (2)	0.71094 (10)	1.1439 (4)	0.0180 (5)
O8	1.02950 (19)	0.29837 (9)	0.2960 (4)	0.0183 (5)
O9	0.11946 (18)	0.06361 (10)	0.8481 (4)	0.0152 (5)
C1	0.1406 (3)	0.46845 (14)	0.5090 (6)	0.0129 (7)
C2	0.0532 (3)	0.50081 (13)	0.4269 (5)	0.0113 (6)
H2	−0.0156	0.4866	0.3620	0.014*
C3	0.0669 (3)	0.55406 (14)	0.4403 (6)	0.0127 (7)
C4	0.1686 (3)	0.57493 (13)	0.5353 (6)	0.0127 (7)
H4	0.1783	0.6112	0.5452	0.015*
C5	0.2549 (3)	0.54226 (13)	0.6147 (5)	0.0125 (7)
C6	0.2412 (3)	0.48950 (13)	0.6015 (6)	0.0136 (7)
H6	0.3008	0.4675	0.6558	0.016*
C7	0.1295 (3)	0.41098 (14)	0.4918 (6)	0.0150 (7)
C8	−0.0277 (3)	0.58794 (13)	0.3392 (6)	0.0124 (7)
C9	0.3641 (3)	0.56526 (13)	0.7065 (6)	0.0134 (7)
C10	0.6414 (3)	0.77853 (13)	0.8312 (6)	0.0146 (7)
H10	0.6164	0.8119	0.7733	0.017*
C11	0.7469 (3)	0.77035 (14)	0.9492 (6)	0.0160 (7)
H11	0.7947	0.7979	0.9756	0.019*
C12	0.7854 (3)	0.72007 (14)	1.0328 (6)	0.0156 (7)
C13	0.7089 (3)	0.68087 (13)	0.9850 (6)	0.0161 (7)
H13	0.7308	0.6467	1.0352	0.019*
C14	0.6033 (3)	0.69193 (15)	0.8667 (6)	0.0182 (7)
H14	0.5527	0.6655	0.8355	0.022*
C15	0.7479 (3)	0.28586 (15)	0.0073 (6)	0.0203 (8)
H15	0.6867	0.3060	−0.0321	0.024*
C16	0.8446 (3)	0.30826 (14)	0.1192 (6)	0.0188 (7)
H16	0.8495	0.3439	0.1542	0.023*
C17	0.9382 (3)	0.27898 (14)	0.1843 (6)	0.0163 (7)
C18	0.9227 (3)	0.22593 (14)	0.1212 (7)	0.0195 (8)
H18	0.9820	0.2044	0.1594	0.023*
C19	0.8238 (3)	0.20564 (15)	0.0069 (6)	0.0216 (8)
H19	0.8153	0.1703	−0.0341	0.026*
C20	0.0841 (3)	0.07837 (14)	0.2819 (6)	0.0189 (8)
H20	0.0307	0.0861	0.1349	0.023*
C21	0.0613 (3)	0.07946 (14)	0.4590 (6)	0.0183 (7)
H21	−0.0070	0.0890	0.4347	0.022*
C22	0.1399 (3)	0.06629 (13)	0.6804 (6)	0.0142 (7)
C23	0.2420 (3)	0.05643 (13)	0.7041 (6)	0.0162 (7)
H23	0.2985	0.0498	0.8488	0.019*
C24	0.2592 (3)	0.05641 (13)	0.5203 (6)	0.0178 (7)
H24	0.3276	0.0492	0.5386	0.021*

	U11	U22	U33	U12	U13	U23
N1	0.0100 (15)	0.0280 (17)	0.0156 (15)	0.0043 (13)	0.0042 (13)	−0.0001 (13)
N2	0.0156 (16)	0.0321 (19)	0.0161 (15)	−0.0092 (13)	0.0075 (13)	−0.0042 (13)
N3	0.0239 (17)	0.0187 (15)	0.0168 (16)	−0.0008 (12)	0.0133 (14)	0.0001 (12)
O1	0.0166 (13)	0.0125 (11)	0.0273 (14)	−0.0030 (10)	0.0070 (11)	−0.0028 (11)
O2	0.0153 (13)	0.0174 (13)	0.0278 (14)	0.0012 (10)	0.0068 (11)	0.0000 (11)
O3	0.0109 (12)	0.0159 (12)	0.0276 (14)	0.0039 (10)	0.0050 (11)	0.0045 (11)
O4	0.0122 (12)	0.0176 (12)	0.0200 (13)	−0.0002 (10)	0.0080 (10)	0.0008 (10)
O5	0.0093 (12)	0.0201 (13)	0.0260 (14)	−0.0011 (10)	0.0086 (11)	−0.0021 (11)
O6	0.0125 (12)	0.0207 (14)	0.0291 (15)	−0.0026 (10)	0.0069 (11)	−0.0036 (11)
O7	0.0101 (12)	0.0183 (13)	0.0212 (13)	−0.0004 (9)	0.0035 (10)	0.0010 (10)
O8	0.0121 (12)	0.0149 (12)	0.0237 (13)	−0.0007 (9)	0.0047 (11)	−0.0006 (10)
O9	0.0113 (12)	0.0231 (13)	0.0121 (12)	−0.0027 (10)	0.0062 (10)	−0.0014 (10)
C1	0.0130 (17)	0.0189 (17)	0.0074 (15)	−0.0004 (13)	0.0051 (13)	−0.0004 (12)
C2	0.0080 (15)	0.0178 (16)	0.0078 (15)	−0.0014 (12)	0.0033 (12)	−0.0016 (12)
C3	0.0148 (16)	0.0178 (17)	0.0074 (15)	0.0003 (13)	0.0066 (13)	−0.0011 (13)
C4	0.0149 (17)	0.0137 (16)	0.0098 (15)	−0.0011 (12)	0.0059 (13)	0.0002 (13)
C5	0.0131 (16)	0.0191 (17)	0.0054 (14)	0.0003 (13)	0.0043 (13)	0.0003 (13)
C6	0.0113 (16)	0.0179 (17)	0.0113 (15)	0.0057 (13)	0.0048 (13)	0.0021 (13)
C7	0.0144 (17)	0.0181 (17)	0.0133 (15)	−0.0016 (13)	0.0072 (14)	−0.0002 (13)
C8	0.0100 (16)	0.0173 (16)	0.0110 (16)	0.0005 (13)	0.0058 (13)	−0.0001 (13)
C9	0.0123 (17)	0.0157 (17)	0.0099 (16)	−0.0004 (12)	0.0032 (13)	0.0012 (12)
C10	0.0179 (17)	0.0166 (17)	0.0116 (15)	0.0062 (13)	0.0088 (13)	0.0015 (13)
C11	0.0176 (18)	0.0166 (16)	0.0159 (16)	−0.0035 (14)	0.0095 (14)	−0.0022 (13)
C12	0.0137 (17)	0.0227 (18)	0.0094 (16)	0.0010 (14)	0.0045 (14)	−0.0018 (13)
C13	0.0185 (18)	0.0120 (16)	0.0171 (17)	0.0014 (13)	0.0076 (14)	0.0016 (13)
C14	0.0181 (18)	0.0208 (18)	0.0161 (17)	−0.0020 (14)	0.0082 (15)	−0.0021 (14)
C15	0.0180 (18)	0.029 (2)	0.0142 (18)	0.0038 (15)	0.0078 (15)	0.0010 (15)
C16	0.0192 (19)	0.0183 (17)	0.0205 (18)	0.0005 (14)	0.0106 (16)	−0.0013 (15)
C17	0.0183 (18)	0.0180 (17)	0.0141 (17)	−0.0040 (14)	0.0089 (14)	0.0003 (14)
C18	0.0186 (19)	0.0179 (18)	0.025 (2)	0.0008 (14)	0.0128 (16)	0.0012 (15)
C19	0.028 (2)	0.0199 (19)	0.0206 (18)	−0.0080 (15)	0.0146 (17)	−0.0044 (15)
C20	0.0232 (19)	0.0206 (18)	0.0116 (16)	−0.0058 (14)	0.0070 (14)	0.0006 (14)
C21	0.0116 (17)	0.0217 (18)	0.0212 (18)	−0.0010 (13)	0.0074 (14)	−0.0010 (15)
C22	0.0175 (17)	0.0133 (16)	0.0157 (17)	−0.0064 (13)	0.0109 (14)	−0.0040 (13)
C23	0.0160 (17)	0.0167 (17)	0.0152 (17)	−0.0009 (14)	0.0067 (14)	0.0004 (14)
C24	0.0157 (17)	0.0146 (17)	0.0248 (19)	−0.0022 (14)	0.0108 (15)	0.0004 (14)

N1—C10	1.347 (5)	C4—H4	0.9500
N1—C14	1.352 (5)	C5—C6	1.382 (5)
N1—H1A	0.8400 (12)	C5—C9	1.517 (5)
N2—C15	1.351 (5)	C6—H6	0.9500
N2—C19	1.353 (5)	C10—C11	1.363 (5)
N2—H2A	0.8400 (11)	C10—H10	0.9500
N3—C24	1.345 (5)	C11—C12	1.429 (5)
N3—C20	1.345 (5)	C11—H11	0.9500
N3—H3A	0.8400 (11)	C12—C13	1.421 (5)
O1—C7	1.325 (4)	C13—C14	1.377 (5)
O1—H1'	0.8400 (11)	C13—H13	0.9500
O2—C7	1.216 (4)	C14—H14	0.9500
O3—C8	1.311 (4)	C15—C16	1.365 (5)
O3—H3'	0.8400 (11)	C15—H15	0.9500
O4—C8	1.217 (4)	C16—C17	1.425 (5)
O5—C9	1.301 (4)	C16—H16	0.9500
O5—H5'	0.8400 (12)	C17—C18	1.429 (5)
O6—C9	1.217 (4)	C18—C19	1.369 (5)
O7—C12	1.280 (4)	C18—H18	0.9500
O8—C17	1.275 (4)	C19—H19	0.9500
O9—C22	1.288 (4)	C20—C21	1.370 (5)
C1—C2	1.394 (5)	C20—H20	0.9500
C1—C6	1.394 (5)	C21—C22	1.431 (5)
C1—C7	1.501 (5)	C21—H21	0.9500
C2—C3	1.395 (5)	C22—C23	1.421 (5)
C2—H2	0.9500	C23—C24	1.364 (5)
C3—C4	1.404 (5)	C23—H23	0.9500
C3—C8	1.492 (5)	C24—H24	0.9500
C4—C5	1.389 (5)
C10—N1—C14	121.4 (3)	C10—C11—C12	119.6 (3)
C10—N1—H1A	118 (3)	C10—C11—H11	120.2
C14—N1—H1A	120 (3)	C12—C11—H11	120.2
C15—N2—C19	121.0 (3)	O7—C12—C13	121.9 (3)
C15—N2—H2A	120 (3)	O7—C12—C11	121.4 (3)
C19—N2—H2A	117 (3)	C13—C12—C11	116.7 (3)
C24—N3—C20	121.1 (3)	C14—C13—C12	120.6 (3)
C24—N3—H3A	122 (3)	C14—C13—H13	119.7
C20—N3—H3A	117 (3)	C12—C13—H13	119.7
C7—O1—H1'	110 (3)	N1—C14—C13	120.0 (3)
C8—O3—H3'	118 (3)	N1—C14—H14	120.0
C9—O5—H5'	113 (3)	C13—C14—H14	120.0
C2—C1—C6	119.8 (3)	N2—C15—C16	121.0 (3)
C2—C1—C7	121.7 (3)	N2—C15—H15	119.5
C6—C1—C7	118.4 (3)	C16—C15—H15	119.5
C1—C2—C3	119.9 (3)	C15—C16—C17	121.0 (3)
C1—C2—H2	120.0	C15—C16—H16	119.5
C3—C2—H2	120.0	C17—C16—H16	119.5
C2—C3—C4	119.9 (3)	O8—C17—C16	122.4 (3)
C2—C3—C8	119.0 (3)	O8—C17—C18	122.2 (3)
C4—C3—C8	121.0 (3)	C16—C17—C18	115.4 (3)
C5—C4—C3	119.6 (3)	C19—C18—C17	121.1 (3)
C5—C4—H4	120.2	C19—C18—H18	119.4
C3—C4—H4	120.2	C17—C18—H18	119.4
C6—C5—C4	120.5 (3)	N2—C19—C18	120.5 (3)
C6—C5—C9	120.4 (3)	N2—C19—H19	119.7
C4—C5—C9	119.1 (3)	C18—C19—H19	119.7
C5—C6—C1	120.3 (3)	N3—C20—C21	120.8 (3)
C5—C6—H6	119.8	N3—C20—H20	119.6
C1—C6—H6	119.8	C21—C20—H20	119.6
O2—C7—O1	123.8 (3)	C20—C21—C22	120.4 (3)
O2—C7—C1	122.3 (3)	C20—C21—H21	119.8
O1—C7—C1	113.9 (3)	C22—C21—H21	119.8
O4—C8—O3	124.6 (3)	O9—C22—C23	122.0 (3)
O4—C8—C3	122.8 (3)	O9—C22—C21	122.1 (3)
O3—C8—C3	112.6 (3)	C23—C22—C21	115.9 (3)
O6—C9—O5	125.1 (3)	C24—C23—C22	120.4 (3)
O6—C9—C5	122.4 (3)	C24—C23—H23	119.8
O5—C9—C5	112.5 (3)	C22—C23—H23	119.8
N1—C10—C11	121.6 (3)	N3—C24—C23	121.3 (3)
N1—C10—H10	119.2	N3—C24—H24	119.4
C11—C10—H10	119.2	C23—C24—H24	119.4
C6—C1—C2—C3	−0.8 (5)	C14—N1—C10—C11	−2.5 (5)
C7—C1—C2—C3	−178.1 (3)	N1—C10—C11—C12	1.4 (5)
C1—C2—C3—C4	0.3 (5)	C10—C11—C12—O7	179.9 (3)
C1—C2—C3—C8	176.4 (3)	C10—C11—C12—C13	0.3 (5)
C2—C3—C4—C5	0.2 (5)	O7—C12—C13—C14	179.5 (3)
C8—C3—C4—C5	−175.8 (3)	C11—C12—C13—C14	−1.0 (5)
C3—C4—C5—C6	−0.2 (5)	C10—N1—C14—C13	1.8 (5)
C3—C4—C5—C9	177.0 (3)	C12—C13—C14—N1	0.0 (5)
C4—C5—C6—C1	−0.2 (5)	C19—N2—C15—C16	0.5 (5)
C9—C5—C6—C1	−177.5 (3)	N2—C15—C16—C17	−1.1 (5)
C2—C1—C6—C5	0.8 (5)	C15—C16—C17—O8	−177.4 (3)
C7—C1—C6—C5	178.1 (3)	C15—C16—C17—C18	0.9 (5)
C2—C1—C7—O2	−172.4 (3)	O8—C17—C18—C19	178.1 (3)
C6—C1—C7—O2	10.2 (5)	C16—C17—C18—C19	−0.2 (5)
C2—C1—C7—O1	7.9 (5)	C15—N2—C19—C18	0.2 (6)
C6—C1—C7—O1	−169.4 (3)	C17—C18—C19—N2	−0.4 (6)
C2—C3—C8—O4	3.5 (5)	C24—N3—C20—C21	−1.5 (5)
C4—C3—C8—O4	179.5 (3)	N3—C20—C21—C22	−2.0 (6)
C2—C3—C8—O3	−176.4 (3)	C20—C21—C22—O9	−175.4 (3)
C4—C3—C8—O3	−0.4 (4)	C20—C21—C22—C23	4.8 (5)
C6—C5—C9—O6	−168.8 (3)	O9—C22—C23—C24	175.8 (3)
C4—C5—C9—O6	13.9 (5)	C21—C22—C23—C24	−4.3 (5)
C6—C5—C9—O5	11.8 (4)	C20—N3—C24—C23	2.0 (5)
C4—C5—C9—O5	−165.5 (3)	C22—C23—C24—N3	1.1 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1′···O8i	0.84	1.72	2.555 (3)	173
O3—H3′···O7ii	0.84	1.70	2.489 (3)	156
O5—H5′···O9iii	0.84	1.70	2.531 (4)	170
N1—H1A···O7iv	0.84	1.91	2.712 (4)	158
N2—H2A···O8v	0.84	2.00	2.817 (4)	165
N3—H3A···O9vi	0.84	2.09	2.825 (4)	146
C14—H14···O6	0.95	2.67	3.596 (5)	166
C19—H19···O2vii	0.95	2.48	3.034 (5)	117
C24—H24···O4viii	0.95	2.45	3.067 (6)	123
C13—H13···O9iii	0.95	2.63	3.270 (4)	125
C10—H10···O3ix	0.95	2.42	3.073 (5)	126
C16—H16···O1x	0.95	2.68	3.307 (4)	124
C19—H19···O6xi	0.95	2.57	3.314 (6)	135
C20—H20···O6xii	0.95	2.55	3.499 (4)	176
C23—H23···O4xiii	0.95	2.48	3.310 (4)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1′⋯O8i	0.84	1.72	2.555 (3)	173
O3—H3′⋯O7ii	0.84	1.70	2.489 (3)	156
O5—H5′⋯O9iii	0.84	1.70	2.531 (4)	170
N1—H1A⋯O7iv	0.84	1.91	2.712 (4)	158
N2—H2A⋯O8v	0.84	2.00	2.817 (4)	165
N3—H3A⋯O9vi	0.84	2.09	2.825 (4)	146
C14—H14⋯O6	0.95	2.67	3.596 (5)	166
C19—H19⋯O2vii	0.95	2.48	3.034 (5)	117
C24—H24⋯O4viii	0.95	2.45	3.067 (6)	123
C13—H13⋯O9iii	0.95	2.63	3.270 (4)	125
C10—H10⋯O3ix	0.95	2.42	3.073 (5)	126
C16—H16⋯O1x	0.95	2.68	3.307 (4)	124
C19—H19⋯O6xi	0.95	2.57	3.314 (6)	135
C20—H20⋯O6xii	0.95	2.55	3.499 (4)	176
C23—H23⋯O4xiii	0.95	2.48	3.310 (4)	147

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