Diaqua-(2,2'-bipyridine-5,5'-dicarboxyl-ato-κN,N')(ethyl-enediamine-κN,N')copper(II) 2.5-hydrate.

In the mol-ecule of the title compound, [Cu(C(12)H(6)N(2)O(4))(C(2)H(8)N(2))(H(2)O)(2)]·2.5H(2)O, the Cu(II) atom is six-coordinated in a distorted octa-hedral configuration by two N atoms from a 2,2'-bipyridine-5,5'-dicarboxyl-ate anion, two N atoms from ethyl-enediamine and two O atoms from two water mol-ecules. There are also two and a half water mol-ecules in the asymmetric unit. The planar five-membered ring is nearly coplanar with the adjacent pyridine rings, while the other five-membered ring adopts a twisted conformation, probably due to hydrogen bonding. In the crystal structure, intra- and inter-molecular N-H⋯O and O-H⋯O hydrogen bonds link the mol-ecules.

Related literature

For complexes involving 2,2′-bipyridine-5,5′-dicarboxyl­ate anions, see: Min et al. (2002 ▶); Geary et al. (2003 ▶); Hafizovic et al. (2006 ▶); Schoknechta & Kempe (2004 ▶); Matthews et al. (2004 ▶).

Experimental

Crystal data

[Cu(C12H6N2O4)(C2H8N2)(H2O)2]·2.5H2O

M = 446.92

Monoclinic,

a = 31.730 (6) Å

b = 7.2481 (14) Å

c = 18.421 (4) Å

β = 120.05 (3)°

V = 3667.1 (17) Å3

Z = 8

Mo Kα radiation

μ = 1.25 mm−1

T = 298 (2) K

0.50 × 0.18 × 0.07 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1998 ▶) T min = 0.770, T max = 0.923

13747 measured reflections

4887 independent reflections

4221 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.120

S = 1.10

4887 reflections

301 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.71 e Å−3

Δρmin = −0.64 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808029061/hk2516sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808029061/hk2516Isup2.hkl

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

[Cu(C12H6N2O4)(C2H8N2)(H2O)2]·2.5H2O	F(000) = 1856
Mr = 446.92	Dx = 1.619 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1976 reflections
a = 31.730 (6) Å	θ = 2.2–29.3°
b = 7.2481 (14) Å	µ = 1.25 mm−1
c = 18.421 (4) Å	T = 298 K
β = 120.05 (3)°	Plate, blue
V = 3667.1 (17) Å3	0.50 × 0.18 × 0.07 mm
Z = 8

Bruker SMART CCD area-detector diffractometer	4887 independent reflections
Radiation source: fine-focus sealed tube	4221 reflections with I > 2σ(I)
graphite	Rint = 0.043
φ and ω scans	θmax = 29.3°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	h = −43→43
Tmin = 0.770, Tmax = 0.923	k = −9→9
13747 measured reflections	l = −25→25

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ2(Fo2) + (0.0582P)2 + 5.7488P] where P = (Fo2 + 2Fc2)/3
4887 reflections	(Δ/σ)max = 0.015
301 parameters	Δρmax = 1.71 e Å−3
0 restraints	Δρmin = −0.64 e Å−3

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
Cu1	0.129145 (10)	0.87872 (5)	0.482858 (17)	0.02876 (10)
O1	0.28103 (9)	1.1389 (6)	0.78353 (15)	0.0769 (10)
O2	0.33829 (8)	1.2562 (4)	0.76199 (13)	0.0501 (5)
O3	0.09405 (8)	0.6749 (3)	0.10781 (12)	0.0447 (5)
O4	0.05397 (7)	0.5529 (3)	0.16672 (12)	0.0410 (4)
O5	0.10527 (11)	1.2087 (4)	0.42720 (19)	0.0570 (6)
H5B	0.0955 (18)	1.190 (7)	0.375 (4)	0.078 (15)*
H5C	0.0838 (19)	1.250 (8)	0.424 (3)	0.081 (18)*
O6	0.15861 (10)	0.5703 (4)	0.55005 (19)	0.0513 (6)
H6A	0.1748 (14)	0.577 (5)	0.596 (3)	0.041 (10)*
H6B	0.133 (2)	0.484 (9)	0.535 (4)	0.101 (19)*
O7	0.41911 (13)	1.2811 (5)	0.74176 (19)	0.0621 (7)
H7A	0.3946 (18)	1.303 (7)	0.744 (3)	0.062 (13)*
H7B	0.434 (2)	1.192 (10)	0.764 (4)	0.11 (2)*
O8	0.0000	0.9968 (6)	0.2500	0.0568 (9)
H8B	0.0210 (17)	1.050 (7)	0.252 (4)	0.066 (15)*
O9	0.03530 (9)	0.5945 (4)	−0.05647 (15)	0.0511 (6)
H9B	0.0049 (17)	0.569 (6)	−0.080 (3)	0.063 (12)*
H9C	0.056 (2)	0.608 (7)	0.004 (4)	0.097 (17)*
N1	0.19871 (7)	0.9679 (3)	0.53881 (12)	0.0270 (4)
N2	0.14333 (7)	0.8272 (3)	0.38928 (12)	0.0252 (4)
N3	0.11694 (8)	0.9366 (3)	0.57706 (13)	0.0274 (4)
H3A	0.1385 (13)	0.896 (5)	0.624 (2)	0.043 (9)*
H3B	0.1155 (12)	1.055 (5)	0.581 (2)	0.035 (8)*
N4	0.05847 (7)	0.8043 (3)	0.41939 (14)	0.0300 (4)
H4B	0.0422 (13)	0.848 (5)	0.369 (2)	0.037 (8)*
H4C	0.0557 (12)	0.682 (5)	0.418 (2)	0.037 (8)*
C1	0.22492 (9)	1.0341 (4)	0.61691 (15)	0.0331 (5)
H1	0.2111	1.0336	0.6511	0.040*
C2	0.27180 (8)	1.1035 (3)	0.64927 (15)	0.0298 (5)
C3	0.29927 (10)	1.1729 (4)	0.73932 (16)	0.0384 (6)
C4	0.29229 (8)	1.0998 (3)	0.59865 (15)	0.0290 (5)
H4A	0.3235	1.1457	0.6183	0.035*
C5	0.26621 (8)	1.0276 (3)	0.51827 (14)	0.0271 (4)
H5A	0.2800	1.0220	0.4841	0.033*
C6	0.21916 (8)	0.9637 (3)	0.48967 (13)	0.0226 (4)
C7	0.18787 (8)	0.8846 (3)	0.40512 (13)	0.0223 (4)
C8	0.20220 (8)	0.8669 (3)	0.34572 (14)	0.0279 (4)
H8A	0.2328	0.9074	0.3573	0.033*
C9	0.17036 (9)	0.7882 (3)	0.26864 (14)	0.0284 (5)
H9A	0.1795	0.7759	0.2281	0.034*
C10	0.12496 (8)	0.7278 (3)	0.25224 (14)	0.0257 (4)
C11	0.08798 (9)	0.6439 (3)	0.16880 (14)	0.0293 (5)
C12	0.11346 (8)	0.7489 (4)	0.31536 (14)	0.0287 (5)
H12	0.0834	0.7063	0.3056	0.034*
C13	0.06969 (9)	0.8537 (4)	0.55719 (16)	0.0340 (5)
H13A	0.0571	0.9136	0.5895	0.041*
H13B	0.0738	0.7234	0.5711	0.041*
C14	0.03498 (9)	0.8794 (4)	0.46480 (16)	0.0332 (5)
H14A	0.0047	0.8148	0.4482	0.040*
H14B	0.0278	1.0093	0.4520	0.040*

	U11	U22	U33	U12	U13	U23
Cu1	0.02016 (14)	0.04566 (19)	0.01986 (14)	−0.00232 (11)	0.00958 (11)	−0.00645 (12)
O1	0.0448 (13)	0.154 (3)	0.0339 (11)	−0.0239 (16)	0.0215 (10)	−0.0362 (16)
O2	0.0412 (11)	0.0628 (14)	0.0320 (10)	−0.0159 (10)	0.0077 (9)	−0.0168 (10)
O3	0.0551 (12)	0.0527 (12)	0.0221 (8)	−0.0170 (10)	0.0163 (8)	−0.0079 (8)
O4	0.0333 (9)	0.0507 (11)	0.0298 (9)	−0.0135 (8)	0.0090 (8)	−0.0066 (8)
O5	0.0548 (15)	0.0671 (17)	0.0513 (15)	0.0147 (13)	0.0281 (13)	0.0149 (13)
O6	0.0509 (14)	0.0504 (13)	0.0545 (15)	0.0021 (11)	0.0278 (13)	0.0043 (12)
O7	0.0718 (19)	0.0669 (18)	0.0573 (16)	0.0017 (15)	0.0396 (15)	0.0151 (14)
O8	0.054 (2)	0.057 (2)	0.0453 (19)	0.000	0.0144 (18)	0.000
O9	0.0465 (12)	0.0693 (16)	0.0318 (10)	−0.0222 (11)	0.0153 (9)	−0.0088 (10)
N1	0.0205 (8)	0.0369 (10)	0.0204 (8)	−0.0018 (7)	0.0079 (7)	−0.0056 (8)
N2	0.0213 (8)	0.0325 (10)	0.0206 (8)	−0.0014 (7)	0.0096 (7)	−0.0041 (7)
N3	0.0262 (9)	0.0355 (11)	0.0206 (9)	0.0039 (8)	0.0118 (8)	0.0020 (8)
N4	0.0237 (9)	0.0398 (12)	0.0253 (9)	−0.0018 (8)	0.0115 (8)	−0.0014 (9)
C1	0.0244 (10)	0.0483 (14)	0.0233 (10)	−0.0004 (10)	0.0095 (9)	−0.0095 (10)
C2	0.0249 (10)	0.0344 (12)	0.0219 (10)	0.0017 (9)	0.0056 (8)	−0.0048 (9)
C3	0.0298 (12)	0.0499 (15)	0.0248 (11)	0.0014 (11)	0.0058 (9)	−0.0130 (11)
C4	0.0240 (10)	0.0298 (11)	0.0262 (10)	−0.0037 (8)	0.0073 (8)	−0.0034 (9)
C5	0.0253 (10)	0.0309 (11)	0.0228 (10)	−0.0025 (8)	0.0103 (8)	−0.0013 (9)
C6	0.0226 (9)	0.0227 (10)	0.0197 (9)	0.0010 (8)	0.0085 (8)	−0.0014 (8)
C7	0.0218 (9)	0.0238 (9)	0.0194 (9)	0.0003 (8)	0.0088 (8)	0.0002 (8)
C8	0.0268 (10)	0.0336 (11)	0.0241 (10)	−0.0054 (9)	0.0133 (9)	−0.0024 (9)
C9	0.0325 (11)	0.0333 (12)	0.0211 (10)	−0.0023 (9)	0.0147 (9)	−0.0014 (9)
C10	0.0285 (10)	0.0266 (10)	0.0184 (9)	0.0006 (8)	0.0090 (8)	−0.0009 (8)
C11	0.0330 (11)	0.0280 (11)	0.0199 (9)	−0.0015 (9)	0.0079 (9)	−0.0029 (8)
C12	0.0236 (10)	0.0375 (12)	0.0230 (10)	−0.0036 (9)	0.0102 (8)	−0.0057 (9)
C13	0.0332 (12)	0.0447 (14)	0.0304 (12)	0.0028 (10)	0.0207 (10)	0.0034 (10)
C14	0.0238 (10)	0.0434 (13)	0.0333 (12)	0.0025 (10)	0.0150 (9)	0.0015 (11)

O5—Cu1	2.563 (3)	C4—C5	1.387 (3)
O5—H5B	0.86 (6)	C4—H4A	0.9300
O5—H5C	0.72 (5)	C5—C6	1.390 (3)
O6—Cu1	2.499 (3)	C5—H5A	0.9300
O6—H6A	0.74 (4)	C6—N1	1.353 (3)
O6—H6B	0.96 (6)	C6—C7	1.481 (3)
O7—H7A	0.81 (5)	C7—N2	1.357 (3)
O7—H7B	0.78 (7)	C7—C8	1.385 (3)
O8—H8B	0.76 (6)	C8—C9	1.388 (3)
O9—H9B	0.86 (5)	C8—H8A	0.9300
O9—H9C	0.97 (6)	C9—C10	1.386 (3)
N1—Cu1	2.018 (2)	C9—H9A	0.9300
N2—Cu1	2.0225 (19)	C10—C12	1.390 (3)
N3—Cu1	2.003 (2)	C10—C11	1.518 (3)
N3—H3A	0.85 (4)	C11—O4	1.249 (3)
N3—H3B	0.86 (4)	C11—O3	1.252 (3)
N4—Cu1	2.015 (2)	C12—N2	1.335 (3)
N4—H4B	0.87 (4)	C12—H12	0.9300
N4—H4C	0.89 (4)	C13—N3	1.481 (3)
C1—N1	1.339 (3)	C13—C14	1.506 (4)
C1—C2	1.390 (3)	C13—H13A	0.9700
C1—H1	0.9300	C13—H13B	0.9700
C2—C4	1.378 (3)	C14—N4	1.475 (3)
C2—C3	1.522 (3)	C14—H14A	0.9700
C3—O1	1.237 (4)	C14—H14B	0.9700
C3—O2	1.247 (4)
O5—Cu1—O6	174.49 (10)	C4—C2—C1	118.0 (2)
O5—Cu1—N1	86.22 (11)	C4—C2—C3	122.5 (2)
O5—Cu1—N2	88.78 (10)	C1—C2—C3	119.5 (2)
O5—Cu1—N3	90.26 (10)	O1—C3—O2	126.1 (3)
O5—Cu1—N4	89.86 (11)	O1—C3—C2	116.8 (3)
O6—Cu1—N1	89.50 (10)	O2—C3—C2	117.1 (3)
O6—Cu1—N2	93.97 (10)	C2—C4—C5	119.9 (2)
O6—Cu1—N3	86.84 (10)	C2—C4—H4A	120.1
O6—Cu1—N4	94.56 (11)	C5—C4—H4A	120.1
N3—Cu1—N4	85.24 (9)	C4—C5—C6	118.9 (2)
N3—Cu1—N1	97.29 (9)	C4—C5—H5A	120.5
N4—Cu1—N1	175.34 (9)	C6—C5—H5A	120.5
N3—Cu1—N2	177.97 (9)	N1—C6—C5	121.5 (2)
N4—Cu1—N2	96.54 (8)	N1—C6—C7	114.76 (18)
N1—Cu1—N2	80.87 (8)	C5—C6—C7	123.7 (2)
H5B—O5—H5C	101 (5)	N2—C7—C8	121.3 (2)
H6A—O6—H6B	112 (5)	N2—C7—C6	115.00 (18)
H7A—O7—H7B	118 (6)	C8—C7—C6	123.65 (19)
H9B—O9—H9C	123 (4)	C7—C8—C9	119.2 (2)
Cu1—O5—H5B	100 (3)	C7—C8—H8A	120.4
Cu1—O5—H5C	120 (5)	C9—C8—H8A	120.4
H5B—O5—H5C	100 (6)	C10—C9—C8	119.8 (2)
Cu1—O6—H6B	113 (4)	C10—C9—H9A	120.1
H6A—O6—H6B	112 (5)	C8—C9—H9A	120.1
Cu1—O6—H6A	112 (3)	C9—C10—C12	117.5 (2)
C1—N1—C6	118.6 (2)	C9—C10—C11	122.6 (2)
C1—N1—Cu1	126.54 (17)	C12—C10—C11	119.8 (2)
C6—N1—Cu1	114.80 (14)	O4—C11—O3	125.9 (2)
C12—N2—C7	118.72 (19)	O4—C11—C10	117.5 (2)
C12—N2—Cu1	126.92 (16)	O3—C11—C10	116.7 (2)
C7—N2—Cu1	114.34 (15)	N2—C12—C10	123.4 (2)
C13—N3—Cu1	108.16 (16)	N2—C12—H12	118.3
C13—N3—H3A	108 (2)	C10—C12—H12	118.3
Cu1—N3—H3A	114 (2)	N3—C13—C14	107.8 (2)
C13—N3—H3B	110 (2)	N3—C13—H13A	110.1
Cu1—N3—H3B	108 (2)	C14—C13—H13A	110.1
H3A—N3—H3B	109 (3)	N3—C13—H13B	110.1
C14—N4—Cu1	107.68 (16)	C14—C13—H13B	110.1
C14—N4—H4B	106 (2)	H13A—C13—H13B	108.5
Cu1—N4—H4B	114 (2)	N4—C14—C13	107.7 (2)
C14—N4—H4C	108 (2)	N4—C14—H14A	110.2
Cu1—N4—H4C	110 (2)	C13—C14—H14A	110.2
H4B—N4—H4C	110 (3)	N4—C14—H14B	110.2
N1—C1—C2	123.1 (2)	C13—C14—H14B	110.2
N1—C1—H1	118.5	H14A—C14—H14B	108.5
C2—C1—H1	118.5
C1—N1—Cu1—N3	2.7 (2)	N2—C7—C8—C9	−0.3 (4)
C6—N1—Cu1—N3	−175.05 (17)	C6—C7—C8—C9	179.0 (2)
C1—N1—Cu1—N2	−178.1 (2)	C7—C8—C9—C10	−0.2 (4)
C6—N1—Cu1—N2	4.10 (17)	C8—C9—C10—C12	−0.3 (4)
C12—N2—Cu1—N4	−6.3 (2)	C8—C9—C10—C11	178.8 (2)
C7—N2—Cu1—N4	171.90 (17)	C9—C10—C11—O4	162.4 (2)
C12—N2—Cu1—N1	177.6 (2)	C12—C10—C11—O4	−18.6 (3)
C7—N2—Cu1—N1	−4.19 (16)	C9—C10—C11—O3	−18.6 (4)
C13—N3—Cu1—N4	13.46 (17)	C12—C10—C11—O3	160.4 (2)
C13—N3—Cu1—N1	−170.47 (17)	C9—C10—C12—N2	1.5 (4)
C14—N4—Cu1—N3	15.41 (18)	C11—C10—C12—N2	−177.6 (2)
C14—N4—Cu1—N2	−163.62 (17)	N3—C13—C14—N4	53.5 (3)
N1—C1—C2—C4	−1.4 (4)	C2—C1—N1—C6	1.8 (4)
N1—C1—C2—C3	−178.9 (3)	C2—C1—N1—Cu1	−175.9 (2)
C4—C2—C3—O1	−167.1 (3)	C5—C6—N1—C1	−0.5 (4)
C1—C2—C3—O1	10.4 (4)	C7—C6—N1—C1	178.7 (2)
C4—C2—C3—O2	11.9 (4)	C5—C6—N1—Cu1	177.44 (18)
C1—C2—C3—O2	−170.6 (3)	C7—C6—N1—Cu1	−3.3 (3)
C1—C2—C4—C5	−0.3 (4)	C10—C12—N2—C7	−2.0 (4)
C3—C2—C4—C5	177.2 (2)	C10—C12—N2—Cu1	176.16 (18)
C2—C4—C5—C6	1.4 (4)	C8—C7—N2—C12	1.4 (3)
C4—C5—C6—N1	−1.1 (4)	C6—C7—N2—C12	−178.0 (2)
C4—C5—C6—C7	179.8 (2)	C8—C7—N2—Cu1	−177.01 (18)
N1—C6—C7—N2	−0.2 (3)	C6—C7—N2—Cu1	3.6 (2)
C5—C6—C7—N2	179.0 (2)	C14—C13—N3—Cu1	−39.3 (2)
N1—C6—C7—C8	−179.6 (2)	C13—C14—N4—Cu1	−40.8 (3)
C5—C6—C7—C8	−0.4 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O2i	0.84 (3)	2.11 (3)	2.881 (3)	153 (4)
N3—H3B···O3ii	0.86 (4)	2.21 (4)	3.031 (3)	159 (4)
N4—H4B···O8	0.87 (3)	2.20 (3)	3.054 (3)	171 (4)
N4—H4C···O9iii	0.89 (4)	2.23 (4)	3.069 (4)	158 (4)
O5—H5B···O7iv	0.86 (6)	1.97 (6)	2.807 (4)	164 (5)
O5—H5C···O9ii	0.72 (7)	2.08 (6)	2.779 (5)	165 (5)
O6—H6A···O1i	0.74 (5)	1.99 (5)	2.726 (4)	171 (4)
O6—H6B···O3iii	0.95 (7)	2.51 (7)	3.267 (4)	136 (5)
O7—H7A···O2	0.82 (6)	2.00 (6)	2.776 (5)	158 (5)
O7—H7B···O4v	0.78 (7)	2.11 (7)	2.827 (4)	153 (7)
O8—H8B···O7iv	0.76 (6)	2.22 (6)	2.969 (5)	178 (8)
O9—H9B···O4vi	0.86 (6)	1.96 (5)	2.744 (4)	152 (5)
O9—H9C···O3	0.97 (6)	1.74 (6)	2.706 (3)	169 (4)

O5—Cu1	2.563 (3)
O6—Cu1	2.499 (3)
N1—Cu1	2.018 (2)
N2—Cu1	2.0225 (19)
N3—Cu1	2.003 (2)
N4—Cu1	2.015 (2)

O5—Cu1—O6	174.49 (10)
O5—Cu1—N1	86.22 (11)
O5—Cu1—N2	88.78 (10)
O5—Cu1—N3	90.26 (10)
O5—Cu1—N4	89.86 (11)
O6—Cu1—N1	89.50 (10)
O6—Cu1—N2	93.97 (10)
O6—Cu1—N3	86.84 (10)
O6—Cu1—N4	94.56 (11)
N3—Cu1—N4	85.24 (9)
N3—Cu1—N1	97.29 (9)
N4—Cu1—N1	175.34 (9)
N3—Cu1—N2	177.97 (9)
N4—Cu1—N2	96.54 (8)
N1—Cu1—N2	80.87 (8)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O2i	0.84 (3)	2.11 (3)	2.881 (3)	153 (4)
N3—H3B⋯O3ii	0.86 (4)	2.21 (4)	3.031 (3)	159 (4)
N4—H4B⋯O8	0.87 (3)	2.20 (3)	3.054 (3)	171 (4)
N4—H4C⋯O9iii	0.89 (4)	2.23 (4)	3.069 (4)	158 (4)
O5—H5B⋯O7iv	0.86 (6)	1.97 (6)	2.807 (4)	164 (5)
O5—H5C⋯O9ii	0.72 (7)	2.08 (6)	2.779 (5)	165 (5)
O6—H6A⋯O1i	0.74 (5)	1.99 (5)	2.726 (4)	171 (4)
O6—H6B⋯O3iii	0.95 (7)	2.51 (7)	3.267 (4)	136 (5)
O7—H7A⋯O2	0.82 (6)	2.00 (6)	2.776 (5)	158 (5)
O7—H7B⋯O4v	0.78 (7)	2.11 (7)	2.827 (4)	153 (7)
O8—H8B⋯O7iv	0.76 (6)	2.22 (6)	2.969 (5)	178 (8)
O9—H9B⋯O4vi	0.86 (6)	1.96 (5)	2.744 (4)	152 (5)
O9—H9C⋯O3	0.97 (6)	1.74 (6)	2.706 (3)	169 (4)

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