Bis(N,N'-dimethyl-ethylenediammonium) tris-(oxalato-κO,O)cobaltate(II) dihydrate: an ion-pair complex.

The Co(II) ion in the title complex, (C(4)H(14)N(2))(2)[Co(C(2)O(4))(3)]·2H(2)O, is coordinated by three oxalate ions, resulting in a distorted octa-hedral geometry. Two uncoordinated water mol-ecules are present in asymmetric unit. Inter-molecular N-H⋯O and O-H⋯O hydrogen bonds between the different entities stabilize the crystal structure.

Related literature

For related structures: see Diallo et al. (2008 ▶); Gaye et al. (2011 ▶); Hao et al. (2010 ▶); Kelly et al. (2005 ▶); Zhang et al., (2009 ▶).

Experimental

Crystal data

(C4H14N2)2[Co(C2O4)3]·2H2O

M = 539.37

Monoclinic,

a = 12.625 (3) Å

b = 13.411 (4) Å

c = 16.996 (2) Å

β = 125.91 (2)°

V = 2330.7 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.81 mm−1

T = 293 K

0.50 × 0.48 × 0.26 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997 ▶) T min = 0.720, T max = 0.800

9121 measured reflections

5342 independent reflections

4178 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.133

S = 1.05

5333 reflections

302 parameters

H-atom parameters constrained

Δρmax = 1.24 e Å−3

Δρmin = −0.48 e Å−3

Data collection: DENZO (Otwinowski & Minor, 1997 ▶) and COLLECT (Nonius, 1999 ▶); cell refinement: DENZO and COLLECT; data reduction: SCALEPACK (Otwinowski & Minor, 1997 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶) and CRYSTALBUILDER (Welter, 2006 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811031357/bt5577sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811031357/bt5577Isup2.hkl

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

(C4H14N2)2[Co(C2O4)3]·2H2O	F(000) = 1132
Mr = 539.37	Dx = 1.537 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71070 Å
a = 12.625 (3) Å	Cell parameters from 5427 reflections
b = 13.411 (4) Å	θ = 0.4–27.5°
c = 16.996 (2) Å	µ = 0.81 mm−1
β = 125.91 (2)°	T = 293 K
V = 2330.7 (11) Å3	Cube, pink
Z = 4	0.50 × 0.48 × 0.26 mm

Nonius KappaCCD diffractometer	5342 independent reflections
Radiation source: fine-focus sealed tube, Nonius Kappa CCD	4178 reflections with I > 2σ(I)
graphite	Rint = 0.018
Detector resolution: 9 pixels mm-1	θmax = 27.5°, θmin = 3.4°
φ and ω scans	h = −16→16
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997)	k = −16→17
Tmin = 0.720, Tmax = 0.800	l = −21→22
9121 measured 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)] = 0.047	Hydrogen site location: difference Fourier map
wR(F2) = 0.133	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0615P)2 + 2.554P] where P = (Fo2 + 2Fc2)/3
5333 reflections	(Δ/σ)max = 0.001
302 parameters	Δρmax = 1.24 e Å−3
0 restraints	Δρmin = −0.48 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	0.19856 (3)	0.25025 (2)	0.04584 (2)	0.02870 (12)
O1	0.1066 (2)	0.28305 (14)	0.11324 (14)	0.0380 (4)
O2	0.1676 (2)	0.40241 (14)	0.02043 (14)	0.0373 (4)
O3	0.38888 (19)	0.27837 (17)	0.17225 (13)	0.0404 (5)
O4	0.30589 (18)	0.24570 (14)	−0.01047 (13)	0.0341 (4)
O5	0.19519 (17)	0.09766 (13)	0.06110 (12)	0.0326 (4)
O6	0.02190 (17)	0.21331 (13)	−0.08801 (13)	0.0342 (4)
O7	0.0523 (2)	0.41384 (16)	0.16340 (16)	0.0492 (5)
O8	0.1380 (2)	0.53582 (14)	0.08303 (15)	0.0423 (5)
O9	0.5759 (2)	0.33994 (19)	0.20796 (14)	0.0520 (6)
O10	0.4998 (2)	0.2882 (2)	0.02668 (16)	0.0600 (7)
O11	0.09729 (19)	−0.03816 (13)	−0.02854 (13)	0.0358 (4)
O12	−0.0938 (2)	0.07973 (15)	−0.17267 (13)	0.0477 (5)
C1	0.0942 (3)	0.3754 (2)	0.12066 (18)	0.0321 (5)
C2	0.1363 (3)	0.44434 (19)	0.06991 (18)	0.0319 (5)
C3	0.4665 (3)	0.3009 (2)	0.15178 (18)	0.0335 (6)
C4	0.4215 (3)	0.2767 (2)	0.04675 (18)	0.0328 (5)
C5	0.1060 (2)	0.05329 (18)	−0.01538 (16)	0.0268 (5)
C6	0.0010 (2)	0.12061 (18)	−0.09993 (17)	0.0288 (5)
C11	0.4502 (4)	0.9703 (3)	0.1245 (3)	0.0728 (11)
H11A	0.5370	0.9437	0.1670	0.109*
H11B	0.4438	1.0308	0.1516	0.109*
H11C	0.4316	0.9839	0.0621	0.109*
N10	0.3537 (3)	0.8959 (2)	0.11339 (17)	0.0477 (6)
H10N	0.3732	0.8813	0.1722	0.057*
H10M	0.2729	0.9225	0.0771	0.057*
C12	0.3555 (4)	0.8048 (3)	0.0674 (3)	0.0550 (8)
H12A	0.4417	0.7746	0.1064	0.066*
H12B	0.3337	0.8194	0.0035	0.066*
C13	0.2585 (3)	0.7372 (3)	0.0593 (2)	0.0548 (9)
H13A	0.1719	0.7653	0.0144	0.066*
H13B	0.2744	0.7310	0.1222	0.066*
N9	0.2635 (3)	0.6321 (2)	0.02300 (19)	0.0516 (7)
H9N1	0.2019	0.5941	0.0192	0.062*
H9N2	0.2412	0.6386	−0.0377	0.062*
C14	0.3862 (4)	0.5786 (4)	0.0800 (3)	0.0795 (13)
H14A	0.4520	0.6153	0.0807	0.119*
H14B	0.3757	0.5141	0.0518	0.119*
H14C	0.4122	0.5709	0.1452	0.119*
O13	0.7540 (2)	0.3562 (2)	0.14165 (16)	0.0632 (7)
H13O	0.8069	0.3745	0.2082	0.095*
H13W	0.6669	0.3440	0.1227	0.095*
O14	0.2551 (4)	0.4143 (3)	0.3690 (2)	0.1119 (14)
H14O	0.1813	0.4028	0.3031	0.168*
H14W	0.2973	0.3604	0.4146	0.168*
N8	−0.1051 (2)	0.12399 (17)	0.28323 (16)	0.0366 (5)
H8NA	−0.0724	0.1751	0.3256	0.044*
H8NB	−0.0788	0.0667	0.3173	0.044*
N7	0.1385 (2)	0.11853 (17)	0.22373 (15)	0.0323 (5)
H7NA	0.1035	0.0668	0.1821	0.039*
H7NB	0.1129	0.1752	0.1888	0.039*
C7	0.2830 (3)	0.1114 (3)	0.2847 (2)	0.0470 (7)
H7A	0.3200	0.1654	0.3304	0.070*
H7B	0.3126	0.1149	0.2441	0.070*
H7C	0.3098	0.0491	0.3191	0.070*
C8	0.0909 (3)	0.1176 (2)	0.2861 (2)	0.0435 (7)
H8C	0.1306	0.1720	0.3325	0.052*
H8D	0.1152	0.0554	0.3218	0.052*
C9	−0.0551 (3)	0.1289 (2)	0.2227 (2)	0.0431 (7)
H9A	−0.0790	0.1923	0.1889	0.052*
H9B	−0.0944	0.0761	0.1745	0.052*
C10	−0.2507 (3)	0.1290 (3)	0.2196 (2)	0.0522 (8)
H10A	−0.2781	0.1938	0.1902	0.078*
H10B	−0.2828	0.1173	0.2579	0.078*
H10C	−0.2849	0.0792	0.1698	0.078*

	U11	U22	U33	U12	U13	U23
Co1	0.02854 (19)	0.02694 (19)	0.02907 (19)	−0.00288 (13)	0.01603 (15)	−0.00256 (13)
O1	0.0469 (11)	0.0303 (9)	0.0484 (11)	−0.0013 (9)	0.0343 (10)	0.0026 (8)
O2	0.0533 (11)	0.0260 (9)	0.0479 (11)	−0.0014 (8)	0.0383 (10)	−0.0007 (8)
O3	0.0336 (10)	0.0596 (13)	0.0273 (9)	−0.0106 (9)	0.0175 (8)	−0.0065 (9)
O4	0.0287 (9)	0.0466 (11)	0.0263 (9)	−0.0050 (8)	0.0157 (7)	−0.0088 (7)
O5	0.0323 (9)	0.0259 (9)	0.0267 (8)	0.0001 (7)	0.0101 (7)	0.0016 (7)
O6	0.0315 (9)	0.0238 (9)	0.0313 (9)	0.0001 (7)	0.0095 (8)	0.0033 (7)
O7	0.0695 (15)	0.0436 (12)	0.0593 (13)	0.0075 (11)	0.0517 (12)	0.0045 (10)
O8	0.0601 (13)	0.0273 (10)	0.0505 (12)	−0.0033 (9)	0.0385 (11)	−0.0035 (8)
O9	0.0340 (11)	0.0808 (17)	0.0327 (10)	−0.0197 (11)	0.0148 (9)	−0.0160 (10)
O10	0.0396 (12)	0.107 (2)	0.0396 (12)	−0.0170 (13)	0.0268 (10)	−0.0131 (12)
O11	0.0424 (10)	0.0249 (9)	0.0337 (9)	0.0000 (8)	0.0188 (8)	0.0001 (7)
O12	0.0432 (11)	0.0347 (11)	0.0292 (10)	−0.0058 (9)	0.0010 (9)	−0.0006 (8)
C1	0.0327 (13)	0.0331 (13)	0.0326 (13)	0.0011 (11)	0.0203 (11)	0.0018 (10)
C2	0.0355 (14)	0.0286 (13)	0.0332 (13)	−0.0005 (10)	0.0210 (11)	0.0006 (10)
C3	0.0303 (13)	0.0386 (15)	0.0258 (12)	−0.0009 (11)	0.0133 (10)	−0.0023 (10)
C4	0.0292 (13)	0.0390 (14)	0.0273 (12)	−0.0012 (11)	0.0150 (11)	−0.0022 (10)
C5	0.0282 (12)	0.0255 (12)	0.0252 (11)	0.0004 (9)	0.0147 (10)	0.0018 (9)
C6	0.0293 (12)	0.0262 (12)	0.0254 (11)	−0.0004 (10)	0.0128 (10)	0.0013 (9)
C11	0.058 (2)	0.071 (3)	0.086 (3)	−0.004 (2)	0.041 (2)	0.003 (2)
N10	0.0509 (15)	0.0483 (15)	0.0315 (12)	0.0179 (12)	0.0171 (11)	0.0057 (10)
C12	0.056 (2)	0.061 (2)	0.0536 (19)	−0.0043 (17)	0.0353 (17)	−0.0044 (16)
C13	0.0442 (18)	0.081 (3)	0.0441 (17)	−0.0077 (16)	0.0286 (15)	−0.0094 (16)
N9	0.0537 (16)	0.0543 (16)	0.0420 (14)	−0.0178 (13)	0.0253 (13)	0.0014 (12)
C14	0.059 (2)	0.085 (3)	0.088 (3)	0.000 (2)	0.040 (2)	0.028 (2)
O13	0.0463 (13)	0.104 (2)	0.0393 (12)	−0.0317 (13)	0.0251 (10)	−0.0199 (12)
O14	0.138 (3)	0.080 (2)	0.077 (2)	−0.014 (2)	0.040 (2)	0.0358 (18)
N8	0.0499 (14)	0.0315 (11)	0.0385 (12)	−0.0079 (10)	0.0315 (11)	−0.0056 (9)
N7	0.0361 (11)	0.0314 (11)	0.0307 (10)	−0.0083 (9)	0.0204 (9)	−0.0060 (9)
C7	0.0385 (15)	0.059 (2)	0.0353 (14)	−0.0051 (14)	0.0171 (12)	0.0006 (13)
C8	0.0480 (16)	0.0519 (18)	0.0325 (14)	−0.0062 (14)	0.0248 (13)	−0.0056 (12)
C9	0.0486 (17)	0.0490 (17)	0.0361 (14)	0.0001 (14)	0.0273 (13)	0.0006 (12)
C10	0.0488 (18)	0.055 (2)	0.0487 (18)	0.0006 (15)	0.0261 (15)	0.0021 (15)

Co1—O5	2.0663 (19)	C13—H13A	0.9700
Co1—O4	2.0680 (19)	C13—H13B	0.9700
Co1—O2	2.075 (2)	N9—C14	1.446 (5)
Co1—O1	2.1004 (19)	N9—H9N1	0.9000
Co1—O6	2.1079 (19)	N9—H9N2	0.9000
Co1—O3	2.116 (2)	C14—H14A	0.9600
O1—C1	1.264 (3)	C14—H14B	0.9600
O2—C2	1.253 (3)	C14—H14C	0.9600
O3—C3	1.254 (3)	O13—H13O	0.9484
O4—C4	1.259 (3)	O13—H13W	0.9606
O5—C5	1.263 (3)	O14—H14O	0.9599
O6—C6	1.262 (3)	O14—H14W	0.9599
O7—C1	1.235 (3)	N8—C9	1.490 (3)
O8—C2	1.245 (3)	N8—C10	1.490 (4)
O9—C3	1.243 (3)	N8—H8NA	0.9000
O10—C4	1.229 (3)	N8—H8NB	0.9000
O11—C5	1.240 (3)	N7—C7	1.480 (4)
O12—C6	1.235 (3)	N7—C8	1.494 (3)
C1—C2	1.555 (3)	N7—H7NA	0.9000
C3—C4	1.557 (3)	N7—H7NB	0.9000
C5—C6	1.550 (3)	C7—H7A	0.9600
C11—N10	1.498 (5)	C7—H7B	0.9600
C11—H11A	0.9600	C7—H7C	0.9600
C11—H11B	0.9600	C8—C9	1.501 (4)
C11—H11C	0.9600	C8—H8C	0.9700
N10—C12	1.458 (4)	C8—H8D	0.9700
N10—H10N	0.9000	C9—H9A	0.9700
N10—H10M	0.9000	C9—H9B	0.9700
C12—C13	1.463 (5)	C10—H10A	0.9600
C12—H12A	0.9700	C10—H10B	0.9600
C12—H12B	0.9700	C10—H10C	0.9600
C13—N9	1.555 (5)
O5—Co1—O4	95.52 (8)	C12—C13—N9	111.9 (3)
O5—Co1—O2	170.01 (8)	C12—C13—H13A	109.2
O4—Co1—O2	91.57 (7)	N9—C13—H13A	109.2
O5—Co1—O1	94.60 (7)	C12—C13—H13B	109.2
O4—Co1—O1	168.55 (7)	N9—C13—H13B	109.2
O2—Co1—O1	79.08 (7)	H13A—C13—H13B	107.9
O5—Co1—O6	79.40 (7)	C14—N9—C13	117.4 (3)
O4—Co1—O6	93.41 (8)	C14—N9—H9N1	107.9
O2—Co1—O6	93.19 (8)	C13—N9—H9N1	107.9
O1—Co1—O6	93.70 (8)	C14—N9—H9N2	107.9
O5—Co1—O3	98.27 (8)	C13—N9—H9N2	107.9
O4—Co1—O3	79.23 (7)	H9N1—N9—H9N2	107.2
O2—Co1—O3	89.95 (9)	N9—C14—H14A	109.5
O1—Co1—O3	94.04 (8)	N9—C14—H14B	109.5
O6—Co1—O3	172.08 (8)	H14A—C14—H14B	109.5
C1—O1—Co1	113.60 (16)	N9—C14—H14C	109.5
C2—O2—Co1	113.38 (16)	H14A—C14—H14C	109.5
C3—O3—Co1	111.60 (16)	H14B—C14—H14C	109.5
C4—O4—Co1	114.24 (16)	H13O—O13—H13W	108.1
C5—O5—Co1	114.15 (15)	H14O—O14—H14W	121.4
C6—O6—Co1	113.20 (15)	C9—N8—C10	109.8 (2)
O7—C1—O1	126.1 (2)	C9—N8—H8NA	109.7
O7—C1—C2	118.8 (2)	C10—N8—H8NA	109.7
O1—C1—C2	115.1 (2)	C9—N8—H8NB	109.7
O8—C2—O2	125.7 (2)	C10—N8—H8NB	109.7
O8—C2—C1	117.5 (2)	H8NA—N8—H8NB	108.2
O2—C2—C1	116.8 (2)	C7—N7—C8	110.2 (2)
O9—C3—O3	125.8 (2)	C7—N7—H7NA	109.6
O9—C3—C4	117.5 (2)	C8—N7—H7NA	109.6
O3—C3—C4	116.7 (2)	C7—N7—H7NB	109.6
O10—C4—O4	125.7 (2)	C8—N7—H7NB	109.6
O10—C4—C3	118.7 (2)	H7NA—N7—H7NB	108.1
O4—C4—C3	115.6 (2)	N7—C7—H7A	109.5
O11—C5—O5	125.7 (2)	N7—C7—H7B	109.5
O11—C5—C6	118.1 (2)	H7A—C7—H7B	109.5
O5—C5—C6	116.2 (2)	N7—C7—H7C	109.5
O12—C6—O6	125.9 (2)	H7A—C7—H7C	109.5
O12—C6—C5	118.0 (2)	H7B—C7—H7C	109.5
O6—C6—C5	116.1 (2)	N7—C8—C9	109.1 (2)
N10—C11—H11A	109.5	N7—C8—H8C	109.9
N10—C11—H11B	109.5	C9—C8—H8C	109.9
H11A—C11—H11B	109.5	N7—C8—H8D	109.9
N10—C11—H11C	109.5	C9—C8—H8D	109.9
H11A—C11—H11C	109.5	H8C—C8—H8D	108.3
H11B—C11—H11C	109.5	N8—C9—C8	109.8 (2)
C12—N10—C11	111.0 (3)	N8—C9—H9A	109.7
C12—N10—H10N	109.4	C8—C9—H9A	109.7
C11—N10—H10N	109.4	N8—C9—H9B	109.7
C12—N10—H10M	109.4	C8—C9—H9B	109.7
C11—N10—H10M	109.4	H9A—C9—H9B	108.2
H10N—N10—H10M	108.0	N8—C10—H10A	109.5
N10—C12—C13	107.1 (3)	N8—C10—H10B	109.5
N10—C12—H12A	110.3	H10A—C10—H10B	109.5
C13—C12—H12A	110.3	N8—C10—H10C	109.5
N10—C12—H12B	110.3	H10A—C10—H10C	109.5
C13—C12—H12B	110.3	H10B—C10—H10C	109.5
H12A—C12—H12B	108.6
O5—Co1—O1—C1	177.89 (18)	Co1—O1—C1—O7	−174.5 (2)
O4—Co1—O1—C1	25.8 (5)	Co1—O1—C1—C2	5.8 (3)
O2—Co1—O1—C1	−9.93 (18)	Co1—O2—C2—O8	164.7 (2)
O6—Co1—O1—C1	−102.47 (19)	Co1—O2—C2—C1	−14.1 (3)
O3—Co1—O1—C1	79.24 (19)	O7—C1—C2—O8	7.1 (4)
O5—Co1—O2—C2	64.5 (5)	O1—C1—C2—O8	−173.2 (2)
O4—Co1—O2—C2	−160.22 (19)	O7—C1—C2—O2	−174.1 (3)
O1—Co1—O2—C2	13.13 (18)	O1—C1—C2—O2	5.7 (4)
O6—Co1—O2—C2	106.28 (19)	Co1—O3—C3—O9	164.8 (3)
O3—Co1—O2—C2	−80.99 (19)	Co1—O3—C3—C4	−15.7 (3)
O5—Co1—O3—C3	108.9 (2)	Co1—O4—C4—O10	−174.0 (3)
O4—Co1—O3—C3	14.76 (19)	Co1—O4—C4—C3	6.7 (3)
O2—Co1—O3—C3	−76.8 (2)	O9—C3—C4—O10	6.8 (4)
O1—Co1—O3—C3	−155.9 (2)	O3—C3—C4—O10	−172.7 (3)
O6—Co1—O3—C3	36.6 (7)	O9—C3—C4—O4	−173.8 (3)
O5—Co1—O4—C4	−108.70 (19)	O3—C3—C4—O4	6.6 (4)
O2—Co1—O4—C4	78.35 (19)	Co1—O5—C5—O11	167.8 (2)
O1—Co1—O4—C4	43.4 (5)	Co1—O5—C5—C6	−10.8 (3)
O6—Co1—O4—C4	171.64 (19)	Co1—O6—C6—O12	−178.4 (2)
O3—Co1—O4—C4	−11.30 (19)	Co1—O6—C6—C5	0.7 (3)
O4—Co1—O5—C5	−83.76 (17)	O11—C5—C6—O12	7.4 (4)
O2—Co1—O5—C5	51.3 (5)	O5—C5—C6—O12	−173.9 (2)
O1—Co1—O5—C5	101.59 (18)	O11—C5—C6—O6	−171.7 (2)
O6—Co1—O5—C5	8.69 (17)	O5—C5—C6—O6	7.0 (3)
O3—Co1—O5—C5	−163.64 (17)	C11—N10—C12—C13	−179.8 (3)
O5—Co1—O6—C6	−4.67 (17)	N10—C12—C13—N9	−172.8 (3)
O4—Co1—O6—C6	90.32 (18)	C12—C13—N9—C14	58.1 (4)
O2—Co1—O6—C6	−177.91 (18)	C7—N7—C8—C9	177.9 (3)
O1—Co1—O6—C6	−98.67 (18)	C10—N8—C9—C8	−176.6 (3)
O3—Co1—O6—C6	68.9 (6)	N7—C8—C9—N8	177.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N9—H9N1···O8	0.90	1.86	2.668 (3)	148.
O14—H14O···O7	0.96	1.94	2.876 (4)	163.
N7—H7NB···O1	0.90	1.90	2.769 (3)	161.
O13—H13W···O10	0.96	1.91	2.755 (3)	146.
N10—H10M···O11i	0.90	1.94	2.814 (3)	165.
N10—H10N···O9ii	0.90	1.83	2.721 (3)	173.
N9—H9N2···O13iii	0.90	1.80	2.679 (3)	163.
N8—H8NA···O6iv	0.90	1.94	2.829 (3)	170.
N8—H8NB···O7v	0.90	2.07	2.916 (3)	156.
N8—H8NB···O8v	0.90	2.25	2.801 (3)	119.
N7—H7NA···O12vi	0.90	1.97	2.751 (3)	144.
O13—H13O···O12vii	0.95	1.75	2.698 (3)	174.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N9—H9N1⋯O8	0.90	1.86	2.668 (3)	148
O14—H14O⋯O7	0.96	1.94	2.876 (4)	163
N7—H7NB⋯O1	0.90	1.90	2.769 (3)	161
O13—H13W⋯O10	0.96	1.91	2.755 (3)	146
N10—H10M⋯O11i	0.90	1.94	2.814 (3)	165
N10—H10N⋯O9ii	0.90	1.83	2.721 (3)	173
N9—H9N2⋯O13iii	0.90	1.80	2.679 (3)	163
N8—H8NA⋯O6iv	0.90	1.94	2.829 (3)	170
N8—H8NB⋯O7v	0.90	2.07	2.916 (3)	156
N8—H8NB⋯O8v	0.90	2.25	2.801 (3)	119
N7—H7NA⋯O12vi	0.90	1.97	2.751 (3)	144
O13—H13O⋯O12vii	0.95	1.75	2.698 (3)	174

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