Diacridinium trans-diaqua-bis(pyrazine-2,3-dicarboxyl-ato)cobaltate(II) hexa-hydrate.

The title compound, (C(13)H(10)N)(2)[Co(C(6)H(2)N(2)O(4))(2)(H(2)O)(2)]·6H(2)O, consists of mononuclear trans-[Co(pz-2,3-dc)(2)(H(2)O)(2)](2-) complex anions, (acrH)(+) cations and uncoordinated water mol-ecules (acr is acridine and pz-2,3-dcH(2) is pyrazine-2,3-dicarboxylic acid). The Co(II) atom, which lies on a crystallographic center of symmetry, has a slightly distorted octa-hedral coordination environment, with two N and two O atoms from the (pz-2,3-dc)(2-) ligands in the equatorial plane and with two water mol-ecules in axial positions. In the crystal, the components are held together by two distinct N-H⋯O and C-H⋯O hydrogen bonds with R(2) (2)(8) graph-sets. The coordinated and uncoordinated water mol-ecules are also involved in O-H⋯O hydrogen bonds, which lead to the formation of layers with R(3) (3)(12) graph-set motifs. Extensive π-π stacking inter-actions between parallel aromatic rings of the acridinium ions, with distances ranging from 3.533 (1) to 3.613 (1) Å, occur in the structure.

Related literature

For the crystal structure of pyrazine-2,3-dicarboxylic acid (pz-2,3-dcH2), see: Takusagawa & Shimada (1973 ▶). For complexes of (pz-2,3-dcH2) and manganese, copper, zinc, iron and cadmium, see: Zou et al. (1999 ▶); Konar et al. (2004 ▶); Li et al. (2003 ▶); Xu et al. (2008 ▶); Ma et al. (2006 ▶). For complexes of (pz-2,3-dcH2) with main group metals such as calcium, magnesium and sodium, see: Ptasiewicz-Bak & Leciejewicz (1997a ▶,b ▶); Tombul et al. (2006 ▶). For related structures of CoII complexes with py-2,6-dcH2, see: Aghabozorg et al. (2007 ▶, 2009 ▶); Aghabozorg, Attar Gharamaleki et al. (2008 ▶). For a review article on proton-transfer agents and their metal complexes, see: Aghabozorg, Manteghi & Sheshmani (2008 ▶).

Experimental

Crystal data

(C13H10N)2[Co(C6H2N2O4)2(H2O)2]·6H2O

M = 895.69

Triclinic,

a = 6.9434 (15) Å

b = 9.682 (2) Å

c = 15.660 (5) Å

α = 94.60 (2)°

β = 98.59 (2)°

γ = 110.656 (16)°

V = 963.9 (4) Å3

Z = 1

Mo Kα radiation

μ = 0.53 mm−1

T = 120 K

0.35 × 0.10 × 0.10 mm

Data collection

Bruker SMART 1000 diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.828, T max = 0.949

10681 measured reflections

5096 independent reflections

3880 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.101

S = 1.00

5096 reflections

277 parameters

H-atom parameters constrained

Δρmax = 0.53 e Å−3

Δρmin = −0.51 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: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809053628/om2301sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809053628/om2301Isup2.hkl

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

(C13H10N)2[Co(C6H2N2O4)2(H2O)2]·6H2O	Z = 1
Mr = 895.69	F(000) = 465
Triclinic, P1	Dx = 1.543 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.9434 (15) Å	Cell parameters from 548 reflections
b = 9.682 (2) Å	θ = 3–30°
c = 15.660 (5) Å	µ = 0.53 mm−1
α = 94.60 (2)°	T = 120 K
β = 98.59 (2)°	Needles, yellow
γ = 110.656 (16)°	0.35 × 0.10 × 0.10 mm
V = 963.9 (4) Å3

Bruker SMART 1000 diffractometer	5096 independent reflections
Radiation source: fine-focus sealed tube	3880 reflections with I > 2σ(I)
graphite	Rint = 0.028
φ and ω scans	θmax = 29.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.828, Tmax = 0.949	k = −13→13
10681 measured reflections	l = −21→21

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)] = 0.042	Hydrogen site location: difference Fourier map
wR(F2) = 0.101	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0367P)2 + 0.699P] where P = (Fo2 + 2Fc2)/3
5096 reflections	(Δ/σ)max < 0.001
277 parameters	Δρmax = 0.53 e Å−3
0 restraints	Δρmin = −0.51 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
Co1	0.5000	1.0000	0.0000	0.01687 (10)
O1W	0.7405 (2)	1.11233 (14)	0.10425 (8)	0.0206 (3)
H1WA	0.8327	1.0726	0.1206	0.025*
H1WB	0.7989	1.2121	0.1140	0.025*
O1	0.3091 (2)	0.90307 (14)	0.08669 (8)	0.0183 (3)
O2	0.2750 (2)	0.74313 (15)	0.18449 (9)	0.0234 (3)
O3	0.3583 (2)	0.45588 (14)	0.18785 (9)	0.0209 (3)
O4	0.6398 (2)	0.63005 (15)	0.27515 (8)	0.0228 (3)
N1	0.5784 (2)	0.81013 (16)	0.01910 (10)	0.0164 (3)
C2	0.5084 (3)	0.74911 (19)	0.08802 (11)	0.0153 (3)
C3	0.5842 (3)	0.64696 (19)	0.12446 (11)	0.0155 (3)
N4	0.7276 (2)	0.60676 (17)	0.09142 (10)	0.0184 (3)
C5	0.7905 (3)	0.6652 (2)	0.02152 (12)	0.0190 (4)
H5	0.8889	0.6364	−0.0040	0.023*
C6	0.7162 (3)	0.7669 (2)	−0.01489 (12)	0.0184 (4)
H6	0.7641	0.8063	−0.0648	0.022*
C7	0.3499 (3)	0.8006 (2)	0.12333 (11)	0.0164 (4)
C8	0.5162 (3)	0.5715 (2)	0.20244 (12)	0.0176 (4)
N9	0.6756 (2)	0.47469 (17)	0.40425 (10)	0.0178 (3)
H9	0.6439	0.5260	0.3606	0.021*
C10	0.6512 (3)	0.3295 (2)	0.38850 (12)	0.0180 (4)
C11	0.5757 (3)	0.2510 (2)	0.30266 (12)	0.0219 (4)
H11	0.5427	0.2997	0.2555	0.026*
C12	0.5512 (3)	0.1052 (2)	0.28880 (13)	0.0254 (4)
H12	0.4993	0.0523	0.2313	0.031*
C13	0.6007 (3)	0.0294 (2)	0.35744 (14)	0.0270 (4)
H13	0.5827	−0.0726	0.3456	0.032*
C14	0.6742 (3)	0.1031 (2)	0.44064 (14)	0.0244 (4)
H14	0.7078	0.0521	0.4865	0.029*
C15	0.7007 (3)	0.2556 (2)	0.45909 (12)	0.0196 (4)
C16	0.7708 (3)	0.3361 (2)	0.54300 (12)	0.0216 (4)
H16	0.8046	0.2886	0.5907	0.026*
C17	0.7918 (3)	0.4849 (2)	0.55801 (12)	0.0209 (4)
C18	0.8584 (3)	0.5710 (3)	0.64269 (13)	0.0262 (4)
H18	0.8900	0.5263	0.6921	0.031*
C19	0.8771 (3)	0.7159 (3)	0.65353 (13)	0.0289 (5)
H19	0.9211	0.7717	0.7103	0.035*
C20	0.8314 (3)	0.7843 (2)	0.58062 (14)	0.0265 (4)
H20	0.8468	0.8862	0.5893	0.032*
C21	0.7655 (3)	0.7068 (2)	0.49774 (13)	0.0222 (4)
H21	0.7351	0.7541	0.4494	0.027*
C22	0.7435 (3)	0.5551 (2)	0.48544 (12)	0.0182 (4)
O2W	0.0497 (2)	0.83209 (16)	0.29844 (9)	0.0253 (3)
H2WA	0.1136	0.7940	0.2619	0.030*
H2WB	−0.0814	0.7706	0.2906	0.030*
O3W	0.9656 (2)	0.99532 (15)	0.83648 (9)	0.0249 (3)
H3WA	0.8947	1.0289	0.8693	0.030*
H3WB	0.9717	1.0336	0.7911	0.030*
O4W	−0.0631 (2)	0.40692 (16)	0.12903 (11)	0.0354 (4)
H4WA	0.0802	0.4505	0.1498	0.042*
H4WB	−0.1329	0.4762	0.1288	0.042*

	U11	U22	U33	U12	U13	U23
Co1	0.01858 (19)	0.01624 (18)	0.01689 (18)	0.00754 (14)	0.00289 (14)	0.00433 (13)
O1W	0.0203 (7)	0.0165 (6)	0.0235 (7)	0.0078 (5)	−0.0020 (5)	0.0013 (5)
O1	0.0197 (7)	0.0186 (6)	0.0206 (7)	0.0107 (5)	0.0053 (5)	0.0055 (5)
O2	0.0269 (7)	0.0250 (7)	0.0257 (7)	0.0136 (6)	0.0131 (6)	0.0110 (6)
O3	0.0201 (7)	0.0187 (7)	0.0229 (7)	0.0056 (5)	0.0034 (5)	0.0059 (5)
O4	0.0231 (7)	0.0261 (7)	0.0162 (6)	0.0059 (6)	0.0014 (5)	0.0056 (5)
N1	0.0192 (8)	0.0143 (7)	0.0147 (7)	0.0058 (6)	0.0022 (6)	0.0014 (6)
C2	0.0153 (8)	0.0130 (8)	0.0158 (8)	0.0048 (7)	0.0003 (7)	−0.0004 (6)
C3	0.0170 (8)	0.0138 (8)	0.0145 (8)	0.0051 (7)	0.0009 (7)	0.0010 (6)
N4	0.0200 (8)	0.0174 (8)	0.0190 (8)	0.0083 (6)	0.0035 (6)	0.0034 (6)
C5	0.0209 (9)	0.0189 (9)	0.0187 (9)	0.0088 (8)	0.0051 (7)	0.0008 (7)
C6	0.0210 (9)	0.0187 (9)	0.0170 (9)	0.0083 (7)	0.0051 (7)	0.0040 (7)
C7	0.0161 (9)	0.0155 (8)	0.0167 (8)	0.0053 (7)	0.0018 (7)	0.0019 (7)
C8	0.0196 (9)	0.0191 (9)	0.0184 (9)	0.0112 (7)	0.0048 (7)	0.0059 (7)
N9	0.0164 (7)	0.0229 (8)	0.0145 (7)	0.0076 (6)	0.0024 (6)	0.0049 (6)
C10	0.0140 (8)	0.0232 (9)	0.0172 (9)	0.0066 (7)	0.0035 (7)	0.0055 (7)
C11	0.0197 (9)	0.0261 (10)	0.0186 (9)	0.0075 (8)	0.0021 (7)	0.0038 (8)
C12	0.0225 (10)	0.0259 (10)	0.0235 (10)	0.0049 (8)	0.0031 (8)	0.0005 (8)
C13	0.0239 (10)	0.0197 (10)	0.0358 (12)	0.0060 (8)	0.0055 (9)	0.0045 (8)
C14	0.0207 (10)	0.0260 (10)	0.0292 (10)	0.0095 (8)	0.0057 (8)	0.0125 (8)
C15	0.0140 (8)	0.0267 (10)	0.0198 (9)	0.0083 (8)	0.0045 (7)	0.0076 (8)
C16	0.0160 (9)	0.0334 (11)	0.0187 (9)	0.0107 (8)	0.0054 (7)	0.0113 (8)
C17	0.0152 (9)	0.0336 (11)	0.0155 (9)	0.0103 (8)	0.0036 (7)	0.0052 (8)
C18	0.0193 (10)	0.0457 (13)	0.0158 (9)	0.0152 (9)	0.0028 (7)	0.0025 (9)
C19	0.0205 (10)	0.0442 (13)	0.0200 (10)	0.0124 (9)	0.0025 (8)	−0.0059 (9)
C20	0.0189 (10)	0.0321 (11)	0.0286 (11)	0.0111 (9)	0.0052 (8)	−0.0031 (9)
C21	0.0187 (9)	0.0275 (10)	0.0222 (9)	0.0108 (8)	0.0044 (7)	0.0032 (8)
C22	0.0125 (8)	0.0265 (10)	0.0157 (8)	0.0072 (7)	0.0039 (7)	0.0025 (7)
O2W	0.0227 (7)	0.0293 (8)	0.0244 (7)	0.0093 (6)	0.0071 (6)	0.0042 (6)
O3W	0.0291 (8)	0.0299 (8)	0.0247 (7)	0.0196 (6)	0.0079 (6)	0.0088 (6)
O4W	0.0200 (7)	0.0181 (7)	0.0642 (11)	0.0077 (6)	−0.0030 (7)	0.0021 (7)

Co1—O1W	2.0631 (14)	C11—C12	1.356 (3)
Co1—O1Wi	2.0631 (14)	C11—H11	0.9500
Co1—O1i	2.0846 (14)	C12—C13	1.416 (3)
Co1—O1	2.0846 (14)	C12—H12	0.9500
Co1—N1	2.1237 (15)	C13—C14	1.365 (3)
Co1—N1i	2.1237 (15)	C13—H13	0.9500
O1W—H1WA	0.8741	C14—C15	1.422 (3)
O1W—H1WB	0.8956	C14—H14	0.9500
O1—C7	1.279 (2)	C15—C16	1.396 (3)
O2—C7	1.236 (2)	C16—C17	1.393 (3)
O3—C8	1.235 (2)	C16—H16	0.9500
O4—C8	1.271 (2)	C17—C18	1.426 (3)
N1—C6	1.332 (2)	C17—C22	1.427 (3)
N1—C2	1.344 (2)	C18—C19	1.357 (3)
C2—C3	1.396 (2)	C18—H18	0.9500
C2—C7	1.513 (2)	C19—C20	1.416 (3)
C3—N4	1.344 (2)	C19—H19	0.9500
C3—C8	1.523 (2)	C20—C21	1.372 (3)
N4—C5	1.333 (2)	C20—H20	0.9500
C5—C6	1.386 (3)	C21—C22	1.416 (3)
C5—H5	0.9500	C21—H21	0.9500
C6—H6	0.9500	O2W—H2WA	0.9045
N9—C10	1.352 (2)	O2W—H2WB	0.8778
N9—C22	1.359 (2)	O3W—H3WA	0.8802
N9—H9	0.9214	O3W—H3WB	0.8268
C10—C11	1.416 (3)	O4W—H4WA	0.9266
C10—C15	1.428 (3)	O4W—H4WB	0.9560
O1W—Co1—O1Wi	180.00 (8)	C22—N9—H9	114.8
O1W—Co1—O1i	90.43 (6)	N9—C10—C11	120.24 (16)
O1Wi—Co1—O1i	89.57 (6)	N9—C10—C15	119.61 (17)
O1W—Co1—O1	89.57 (6)	C11—C10—C15	120.15 (18)
O1Wi—Co1—O1	90.43 (6)	C12—C11—C10	119.03 (18)
O1i—Co1—O1	180.0	C12—C11—H11	120.5
O1W—Co1—N1	86.35 (6)	C10—C11—H11	120.5
O1Wi—Co1—N1	93.65 (6)	C11—C12—C13	122.01 (19)
O1i—Co1—N1	101.76 (6)	C11—C12—H12	119.0
O1—Co1—N1	78.24 (6)	C13—C12—H12	119.0
O1W—Co1—N1i	93.65 (6)	C14—C13—C12	119.96 (19)
O1Wi—Co1—N1i	86.35 (6)	C14—C13—H13	120.0
O1i—Co1—N1i	78.24 (6)	C12—C13—H13	120.0
O1—Co1—N1i	101.76 (6)	C13—C14—C15	120.42 (18)
N1—Co1—N1i	180.000 (1)	C13—C14—H14	119.8
Co1—O1W—H1WA	118.4	C15—C14—H14	119.8
Co1—O1W—H1WB	121.9	C16—C15—C14	123.17 (18)
H1WA—O1W—H1WB	111.1	C16—C15—C10	118.39 (18)
C7—O1—Co1	116.07 (11)	C14—C15—C10	118.43 (18)
C6—N1—C2	118.22 (15)	C17—C16—C15	121.10 (17)
C6—N1—Co1	128.58 (12)	C17—C16—H16	119.5
C2—N1—Co1	111.60 (12)	C15—C16—H16	119.5
N1—C2—C3	120.57 (16)	C16—C17—C18	123.23 (18)
N1—C2—C7	116.06 (15)	C16—C17—C22	118.67 (17)
C3—C2—C7	123.36 (16)	C18—C17—C22	118.11 (19)
N4—C3—C2	120.99 (16)	C19—C18—C17	120.76 (19)
N4—C3—C8	114.13 (15)	C19—C18—H18	119.6
C2—C3—C8	124.87 (16)	C17—C18—H18	119.6
C5—N4—C3	117.53 (15)	C18—C19—C20	120.36 (19)
N4—C5—C6	121.74 (17)	C18—C19—H19	119.8
N4—C5—H5	119.1	C20—C19—H19	119.8
C6—C5—H5	119.1	C21—C20—C19	121.5 (2)
N1—C6—C5	120.89 (17)	C21—C20—H20	119.3
N1—C6—H6	119.6	C19—C20—H20	119.3
C5—C6—H6	119.6	C20—C21—C22	118.87 (19)
O2—C7—O1	126.20 (17)	C20—C21—H21	120.6
O2—C7—C2	118.32 (16)	C22—C21—H21	120.6
O1—C7—C2	115.47 (15)	N9—C22—C21	120.25 (17)
O3—C8—O4	127.19 (17)	N9—C22—C17	119.30 (18)
O3—C8—C3	117.46 (16)	C21—C22—C17	120.45 (17)
O4—C8—C3	115.12 (16)	H2WA—O2W—H2WB	107.6
C10—N9—C22	122.92 (16)	H3WA—O3W—H3WB	110.8
C10—N9—H9	122.3	H4WA—O4W—H4WB	113.8
O1W—Co1—O1—C7	−73.69 (13)	C2—C3—C8—O3	86.2 (2)
O1Wi—Co1—O1—C7	106.31 (13)	N4—C3—C8—O4	81.2 (2)
N1—Co1—O1—C7	12.67 (12)	C2—C3—C8—O4	−99.0 (2)
N1i—Co1—O1—C7	−167.33 (12)	C22—N9—C10—C11	178.69 (17)
O1W—Co1—N1—C6	−88.80 (16)	C22—N9—C10—C15	−0.9 (3)
O1Wi—Co1—N1—C6	91.19 (16)	N9—C10—C11—C12	−179.51 (18)
O1i—Co1—N1—C6	0.87 (16)	C15—C10—C11—C12	0.1 (3)
O1—Co1—N1—C6	−179.13 (16)	C10—C11—C12—C13	−0.6 (3)
O1W—Co1—N1—C2	76.28 (12)	C11—C12—C13—C14	0.4 (3)
O1Wi—Co1—N1—C2	−103.72 (12)	C12—C13—C14—C15	0.3 (3)
O1i—Co1—N1—C2	165.96 (12)	C13—C14—C15—C16	178.53 (19)
O1—Co1—N1—C2	−14.04 (12)	C13—C14—C15—C10	−0.7 (3)
C6—N1—C2—C3	2.1 (3)	N9—C10—C15—C16	0.9 (3)
Co1—N1—C2—C3	−164.70 (13)	C11—C10—C15—C16	−178.74 (17)
C6—N1—C2—C7	−179.20 (15)	N9—C10—C15—C14	−179.83 (17)
Co1—N1—C2—C7	14.00 (19)	C11—C10—C15—C14	0.6 (3)
N1—C2—C3—N4	−0.3 (3)	C14—C15—C16—C17	−179.19 (18)
C7—C2—C3—N4	−178.91 (16)	C10—C15—C16—C17	0.1 (3)
N1—C2—C3—C8	179.89 (16)	C15—C16—C17—C18	178.62 (18)
C7—C2—C3—C8	1.3 (3)	C15—C16—C17—C22	−1.0 (3)
C2—C3—N4—C5	−1.6 (3)	C16—C17—C18—C19	179.72 (19)
C8—C3—N4—C5	178.23 (16)	C22—C17—C18—C19	−0.7 (3)
C3—N4—C5—C6	1.7 (3)	C17—C18—C19—C20	−0.3 (3)
C2—N1—C6—C5	−2.0 (3)	C18—C19—C20—C21	0.7 (3)
Co1—N1—C6—C5	162.24 (14)	C19—C20—C21—C22	−0.1 (3)
N4—C5—C6—N1	0.1 (3)	C10—N9—C22—C21	−179.90 (17)
Co1—O1—C7—O2	169.89 (15)	C10—N9—C22—C17	0.0 (3)
Co1—O1—C7—C2	−8.93 (19)	C20—C21—C22—N9	179.06 (17)
N1—C2—C7—O2	177.20 (16)	C20—C21—C22—C17	−0.8 (3)
C3—C2—C7—O2	−4.1 (3)	C16—C17—C22—N9	1.0 (3)
N1—C2—C7—O1	−3.9 (2)	C18—C17—C22—N9	−178.67 (16)
C3—C2—C7—O1	174.79 (16)	C16—C17—C22—C21	−179.16 (17)
N4—C3—C8—O3	−93.7 (2)	C18—C17—C22—C21	1.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O3Wii	0.87	1.81	2.684 (2)	174
O1W—H1WB···O4Wiii	0.90	1.77	2.658 (2)	174
O2W—H2WA···O2	0.90	1.92	2.813 (2)	172
O2W—H2WB···O4iv	0.88	1.90	2.776 (2)	177
O3W—H3WA···O1v	0.88	1.95	2.806 (2)	165
O3W—H3WB···O2Wv	0.83	2.01	2.809 (2)	162
O4W—H4WA···O3	0.93	1.91	2.789 (2)	156
O4W—H4WB···N4iv	0.96	1.92	2.848 (2)	163
N9—H9···O4	0.92	1.74	2.648 (2)	167
C11—H11···O3	0.95	2.50	3.365 (3)	151
C12—H12···O1vi	0.95	2.49	3.431 (3)	171
C16—H16···O2Wvii	0.95	2.46	3.395 (3)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WA⋯O3Wi	0.87	1.81	2.684 (2)	174
O1W—H1WB⋯O4Wii	0.90	1.77	2.658 (2)	174
O2W—H2WA⋯O2	0.90	1.92	2.813 (2)	172
O2W—H2WB⋯O4iii	0.88	1.90	2.776 (2)	177
O3W—H3WA⋯O1iv	0.88	1.95	2.806 (2)	165
O3W—H3WB⋯O2Wiv	0.83	2.01	2.809 (2)	162
O4W—H4WA⋯O3	0.93	1.91	2.789 (2)	156
O4W—H4WB⋯N4iii	0.96	1.92	2.848 (2)	163
N9—H9⋯O4	0.92	1.74	2.648 (2)	167
C11—H11⋯O3	0.95	2.50	3.365 (3)	151
C12—H12⋯O1v	0.95	2.49	3.431 (3)	171
C16—H16⋯O2Wvi	0.95	2.46	3.395 (3)	169

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