3,5-Diamino-4H-1,2,4-triazol-1-ium hydroxonium bis-(pyridine-2,6-di-carboxyl-ato)cobaltate(II) pyridine-2,6-dicarb-oxy-lic acid monohydrate.

The asymmetric unit of the title complex, (C(2)H(6)N(5))(H(3)O)[Co(C(7)H(3)NO(4))(2)]·C(7)H(5)NO(4)·H(2)O, contains a Co(II) ion coordin-ated by four O atoms and two N atoms from two dipicolinate ligands in a disorted octa-hedral environment, a protonated triazole mol-ecule, a neutral pyridine-2,6-dicarb-oxy-lic acid mol-ecule, a hydroxonium ion and a solvent water mol-ecule. In the crystal, the components are linked into a three-dimensional framework by inter-molecular O-H⋯O, N-H⋯O and N-H⋯N and weak C-H⋯O hydrogen bonds. In addition, π-π stacking inter-actions with centroid-centroid distances in the range 3.4809 (7)-3.8145 (6) Å are observed.

Related literature

For the different coordination modes for transition metal–dipicolinate complexes, see: Quaglieri et al. (1972 ▶); Hakansson et al. (1993 ▶); Okabe & Oya (2000 ▶); Aghajani et al. (2009 ▶). For crystal structures of related complexes, see: Yousuf et al. (2011 ▶); Aghabozorg et al. (2009 ▶); Ramos Silva et al. (2008 ▶); Wang et al. (2004 ▶); MacDonald et al. (2000 ▶, 2004 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

(C2H6N5)(H3O)[Co(C7H3NO4)2]·C7H5NO4·H2O

M = 693.42

Triclinic,

a = 8.0209 (2) Å

b = 9.2028 (2) Å

c = 18.7004 (4) Å

α = 98.536 (1)°

β = 96.721 (1)°

γ = 100.515 (1)°

V = 1327.32 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.74 mm−1

T = 100 K

0.78 × 0.59 × 0.35 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.595, T max = 0.781

25547 measured reflections

7698 independent reflections

7360 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.072

S = 1.05

7698 reflections

467 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.48 e Å−3

Δρmin = −0.43 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL and PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811027917/lh5282sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811027917/lh5282Isup2.hkl

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

(C2H6N5)(H3O)[Co(C7H3NO4)2]·C7H5NO4·H2O	Z = 2
Mr = 693.42	F(000) = 710
Triclinic, P1	Dx = 1.735 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.0209 (2) Å	Cell parameters from 9943 reflections
b = 9.2028 (2) Å	θ = 2.9–35.1°
c = 18.7004 (4) Å	µ = 0.74 mm−1
α = 98.536 (1)°	T = 100 K
β = 96.721 (1)°	Block, purple
γ = 100.515 (1)°	0.78 × 0.59 × 0.35 mm
V = 1327.32 (5) Å3

Bruker SMART APEXII CCD area-detector diffractometer	7698 independent reflections
Radiation source: fine-focus sealed tube	7360 reflections with I > 2σ(I)
graphite	Rint = 0.018
φ and ω scans	θmax = 30.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→11
Tmin = 0.595, Tmax = 0.781	k = −12→12
25547 measured reflections	l = −26→26

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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.072	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0325P)2 + 0.8694P] where P = (Fo2 + 2Fc2)/3
7698 reflections	(Δ/σ)max = 0.001
467 parameters	Δρmax = 0.48 e Å−3
0 restraints	Δρmin = −0.43 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.302228 (19)	0.644423 (16)	0.169857 (8)	0.01036 (5)
N1	0.31342 (12)	0.75361 (10)	0.27349 (5)	0.01027 (16)
N2	0.30641 (12)	0.58813 (10)	0.06050 (5)	0.01004 (16)
O1	0.13428 (11)	0.80434 (9)	0.15754 (4)	0.01381 (15)
O2	0.45499 (11)	0.52726 (9)	0.23827 (4)	0.01373 (15)
O3	0.52409 (11)	0.80151 (9)	0.14717 (4)	0.01281 (15)
O4	0.12604 (11)	0.43393 (9)	0.13837 (5)	0.01510 (16)
O5	0.00050 (11)	0.25528 (9)	0.04207 (5)	0.01481 (16)
O6	0.63852 (12)	0.88973 (10)	0.05403 (5)	0.01749 (17)
O7	0.54563 (11)	0.51915 (9)	0.35540 (5)	0.01517 (16)
O8	0.06823 (12)	1.00920 (10)	0.22102 (5)	0.01651 (16)
C1	0.13704 (14)	0.89743 (12)	0.21521 (6)	0.01192 (19)
C2	0.23804 (14)	0.87158 (12)	0.28416 (6)	0.01092 (18)
C3	0.25593 (15)	0.95939 (12)	0.35273 (6)	0.01309 (19)
H3A	0.2025	1.0434	0.3598	0.016*
C4	0.35408 (15)	0.92139 (13)	0.41088 (6)	0.0138 (2)
H4A	0.3688	0.9801	0.4583	0.017*
C5	0.43087 (15)	0.79723 (12)	0.39962 (6)	0.01307 (19)
H5A	0.4972	0.7692	0.4388	0.016*
C6	0.40713 (14)	0.71590 (12)	0.32909 (6)	0.01085 (18)
C7	0.47660 (14)	0.57714 (12)	0.30615 (6)	0.01145 (19)
C8	0.09977 (14)	0.37796 (12)	0.07162 (6)	0.01156 (19)
C9	0.19911 (13)	0.46510 (12)	0.02260 (6)	0.01047 (18)
C10	0.19089 (14)	0.42474 (12)	−0.05245 (6)	0.01231 (19)
H10A	0.1149	0.3366	−0.0788	0.015*
C11	0.29789 (15)	0.51793 (13)	−0.08794 (6)	0.0145 (2)
H11A	0.2944	0.4944	−0.1394	0.017*
C12	0.41009 (15)	0.64579 (13)	−0.04790 (6)	0.0135 (2)
H12A	0.4835	0.7103	−0.0714	0.016*
C13	0.41151 (14)	0.67618 (12)	0.02725 (6)	0.01103 (18)
C14	0.53451 (14)	0.80151 (12)	0.07972 (6)	0.01191 (19)
O9	1.31990 (13)	0.28490 (10)	0.44827 (5)	0.01975 (18)
O10	1.29486 (12)	0.49673 (10)	0.51898 (5)	0.01785 (17)
O11	0.93965 (12)	0.82190 (10)	0.44184 (5)	0.01879 (17)
O12	0.83933 (12)	0.78120 (10)	0.32170 (5)	0.01702 (17)
N8	1.08308 (12)	0.56516 (10)	0.41642 (5)	0.01197 (17)
C17	0.97897 (14)	0.60148 (12)	0.36347 (6)	0.01172 (19)
C18	0.92791 (15)	0.51390 (13)	0.29409 (6)	0.0144 (2)
H18A	0.8533	0.5439	0.2583	0.017*
C19	0.98785 (16)	0.38218 (13)	0.27808 (6)	0.0150 (2)
H19A	0.9538	0.3196	0.2315	0.018*
C20	1.09842 (15)	0.34425 (12)	0.33159 (6)	0.0144 (2)
H20A	1.1440	0.2562	0.3223	0.017*
C21	1.14112 (14)	0.43846 (12)	0.39946 (6)	0.01212 (19)
C22	1.26029 (15)	0.39687 (13)	0.45743 (6)	0.0139 (2)
C23	0.91764 (14)	0.74663 (12)	0.38133 (6)	0.01276 (19)
N3	0.79103 (15)	0.19736 (13)	0.43972 (6)	0.0187 (2)
N4	0.47746 (15)	0.21239 (12)	0.21219 (6)	0.0187 (2)
N5	0.72357 (13)	0.03157 (11)	0.32639 (5)	0.01330 (18)
N6	0.62946 (13)	0.03978 (11)	0.25973 (5)	0.01312 (17)
N7	0.62630 (13)	0.24252 (11)	0.33308 (5)	0.01265 (17)
C15	0.57107 (15)	0.16592 (12)	0.26417 (6)	0.01257 (19)
C16	0.71983 (14)	0.15723 (12)	0.36943 (6)	0.01230 (19)
O1W	0.29638 (15)	0.03156 (12)	0.08229 (6)	0.0269 (2)
O2W	0.87798 (12)	0.10223 (10)	0.12792 (5)	0.01508 (16)
H1N3	0.795 (2)	0.285 (2)	0.4615 (11)	0.027 (5)*
H2N3	0.863 (3)	0.147 (2)	0.4562 (11)	0.036 (5)*
H1N4	0.457 (3)	0.300 (2)	0.2214 (11)	0.033 (5)*
H2N4	0.430 (3)	0.152 (2)	0.1733 (11)	0.027 (5)*
H1N6	0.609 (2)	−0.036 (2)	0.2233 (10)	0.024 (4)*
H1N7	0.605 (3)	0.328 (2)	0.3472 (11)	0.031 (5)*
H1OA	1.351 (3)	0.468 (3)	0.5490 (12)	0.041 (6)*
H12B	0.806 (3)	0.868 (2)	0.3295 (11)	0.036 (5)*
H1W1	0.306 (3)	0.047 (3)	0.0429 (13)	0.043 (6)*
H2W1	0.218 (3)	−0.039 (3)	0.0821 (12)	0.039 (6)*
H2W2	0.947 (3)	0.065 (3)	0.1557 (13)	0.044 (6)*
H1W2	0.930 (4)	0.165 (3)	0.0952 (16)	0.079 (9)*
H3W2	0.796 (3)	0.028 (2)	0.1059 (12)	0.036 (5)*

	U11	U22	U33	U12	U13	U23
Co1	0.01302 (7)	0.00984 (7)	0.00789 (7)	0.00244 (5)	0.00097 (5)	0.00086 (5)
N1	0.0119 (4)	0.0096 (4)	0.0093 (4)	0.0025 (3)	0.0011 (3)	0.0019 (3)
N2	0.0109 (4)	0.0096 (4)	0.0093 (4)	0.0019 (3)	0.0007 (3)	0.0013 (3)
O1	0.0170 (4)	0.0134 (4)	0.0104 (4)	0.0044 (3)	−0.0007 (3)	0.0008 (3)
O2	0.0183 (4)	0.0124 (4)	0.0110 (4)	0.0059 (3)	0.0014 (3)	0.0010 (3)
O3	0.0158 (4)	0.0112 (3)	0.0099 (3)	0.0005 (3)	0.0005 (3)	0.0007 (3)
O4	0.0187 (4)	0.0136 (4)	0.0113 (4)	−0.0010 (3)	0.0022 (3)	0.0020 (3)
O5	0.0165 (4)	0.0115 (4)	0.0142 (4)	−0.0016 (3)	0.0001 (3)	0.0023 (3)
O6	0.0186 (4)	0.0165 (4)	0.0138 (4)	−0.0050 (3)	0.0013 (3)	0.0030 (3)
O7	0.0203 (4)	0.0137 (4)	0.0125 (4)	0.0080 (3)	−0.0011 (3)	0.0025 (3)
O8	0.0218 (4)	0.0152 (4)	0.0144 (4)	0.0098 (3)	−0.0002 (3)	0.0033 (3)
C1	0.0130 (5)	0.0119 (5)	0.0110 (5)	0.0025 (4)	0.0006 (4)	0.0034 (4)
C2	0.0126 (4)	0.0104 (4)	0.0101 (4)	0.0030 (4)	0.0013 (4)	0.0026 (4)
C3	0.0168 (5)	0.0111 (4)	0.0118 (5)	0.0048 (4)	0.0020 (4)	0.0011 (4)
C4	0.0180 (5)	0.0126 (5)	0.0104 (5)	0.0038 (4)	0.0013 (4)	0.0003 (4)
C5	0.0160 (5)	0.0130 (5)	0.0103 (5)	0.0043 (4)	0.0000 (4)	0.0023 (4)
C6	0.0129 (4)	0.0096 (4)	0.0104 (4)	0.0027 (4)	0.0016 (4)	0.0024 (3)
C7	0.0123 (4)	0.0104 (4)	0.0118 (5)	0.0031 (4)	0.0010 (4)	0.0022 (4)
C8	0.0114 (4)	0.0111 (4)	0.0125 (5)	0.0026 (4)	0.0007 (4)	0.0034 (4)
C9	0.0098 (4)	0.0104 (4)	0.0111 (5)	0.0025 (3)	0.0009 (3)	0.0016 (3)
C10	0.0120 (5)	0.0124 (5)	0.0112 (5)	0.0020 (4)	−0.0002 (4)	−0.0001 (4)
C11	0.0156 (5)	0.0172 (5)	0.0097 (5)	0.0024 (4)	0.0013 (4)	0.0011 (4)
C12	0.0143 (5)	0.0151 (5)	0.0108 (5)	0.0012 (4)	0.0019 (4)	0.0029 (4)
C13	0.0110 (4)	0.0104 (4)	0.0110 (5)	0.0014 (4)	0.0008 (4)	0.0013 (3)
C14	0.0128 (5)	0.0106 (4)	0.0112 (5)	0.0014 (4)	0.0004 (4)	0.0009 (4)
O9	0.0265 (5)	0.0157 (4)	0.0186 (4)	0.0114 (3)	0.0001 (3)	0.0019 (3)
O10	0.0241 (4)	0.0166 (4)	0.0129 (4)	0.0101 (3)	−0.0040 (3)	0.0006 (3)
O11	0.0241 (4)	0.0176 (4)	0.0149 (4)	0.0096 (3)	−0.0003 (3)	−0.0005 (3)
O12	0.0231 (4)	0.0135 (4)	0.0149 (4)	0.0088 (3)	−0.0028 (3)	0.0020 (3)
N8	0.0135 (4)	0.0112 (4)	0.0117 (4)	0.0038 (3)	0.0014 (3)	0.0022 (3)
C17	0.0130 (5)	0.0109 (4)	0.0114 (5)	0.0032 (4)	0.0013 (4)	0.0021 (4)
C18	0.0172 (5)	0.0141 (5)	0.0112 (5)	0.0036 (4)	−0.0005 (4)	0.0019 (4)
C19	0.0201 (5)	0.0134 (5)	0.0111 (5)	0.0031 (4)	0.0024 (4)	0.0008 (4)
C20	0.0185 (5)	0.0112 (5)	0.0142 (5)	0.0044 (4)	0.0036 (4)	0.0021 (4)
C21	0.0139 (5)	0.0116 (5)	0.0115 (5)	0.0036 (4)	0.0014 (4)	0.0033 (4)
C22	0.0159 (5)	0.0129 (5)	0.0131 (5)	0.0039 (4)	0.0012 (4)	0.0027 (4)
C23	0.0125 (5)	0.0125 (5)	0.0135 (5)	0.0036 (4)	0.0004 (4)	0.0029 (4)
N3	0.0260 (5)	0.0177 (5)	0.0116 (4)	0.0078 (4)	−0.0019 (4)	−0.0004 (4)
N4	0.0256 (5)	0.0145 (5)	0.0148 (5)	0.0072 (4)	−0.0046 (4)	0.0009 (4)
N5	0.0177 (4)	0.0120 (4)	0.0106 (4)	0.0050 (3)	0.0003 (3)	0.0021 (3)
N6	0.0180 (4)	0.0102 (4)	0.0105 (4)	0.0037 (3)	−0.0004 (3)	0.0006 (3)
N7	0.0170 (4)	0.0101 (4)	0.0109 (4)	0.0047 (3)	0.0008 (3)	0.0004 (3)
C15	0.0152 (5)	0.0099 (4)	0.0120 (5)	0.0017 (4)	0.0019 (4)	0.0013 (4)
C16	0.0145 (5)	0.0111 (4)	0.0116 (5)	0.0029 (4)	0.0022 (4)	0.0024 (4)
O1W	0.0335 (6)	0.0282 (5)	0.0137 (4)	−0.0070 (4)	−0.0010 (4)	0.0062 (4)
O2W	0.0156 (4)	0.0137 (4)	0.0141 (4)	−0.0003 (3)	−0.0010 (3)	0.0031 (3)

Co1—N1	2.0302 (9)	O9—C22	1.2110 (14)
Co1—N2	2.0395 (9)	O10—C22	1.3283 (14)
Co1—O4	2.1363 (8)	O10—H1OA	0.78 (2)
Co1—O1	2.1875 (8)	O11—C23	1.2113 (14)
Co1—O2	2.1967 (8)	O12—C23	1.3242 (13)
Co1—O3	2.2037 (8)	O12—H12B	0.89 (2)
N1—C6	1.3363 (14)	N8—C17	1.3402 (14)
N1—C2	1.3371 (13)	N8—C21	1.3415 (14)
N2—C13	1.3329 (14)	C17—C18	1.3949 (15)
N2—C9	1.3373 (13)	C17—C23	1.5112 (15)
O1—C1	1.2691 (13)	C18—C19	1.3888 (16)
O2—C7	1.2644 (13)	C18—H18A	0.9500
O3—C14	1.2738 (13)	C19—C20	1.3851 (16)
O4—C8	1.2553 (14)	C19—H19A	0.9500
O5—C8	1.2640 (13)	C20—C21	1.3939 (15)
O6—C14	1.2443 (14)	C20—H20A	0.9500
O7—C7	1.2546 (13)	C21—C22	1.4999 (15)
O8—C1	1.2500 (13)	N3—C16	1.3393 (15)
C1—C2	1.5141 (15)	N3—H1N3	0.84 (2)
C2—C3	1.3873 (15)	N3—H2N3	0.86 (2)
C3—C4	1.3920 (15)	N4—C15	1.3271 (15)
C3—H3A	0.9500	N4—H1N4	0.84 (2)
C4—C5	1.3946 (15)	N4—H2N4	0.85 (2)
C4—H4A	0.9500	N5—C16	1.3146 (14)
C5—C6	1.3901 (15)	N5—N6	1.3992 (13)
C5—H5A	0.9500	N6—C15	1.3238 (14)
C6—C7	1.5094 (15)	N6—H1N6	0.876 (19)
C8—C9	1.5081 (15)	N7—C15	1.3553 (14)
C9—C10	1.3882 (15)	N7—C16	1.3765 (14)
C10—C11	1.3950 (16)	N7—H1N7	0.84 (2)
C10—H10A	0.9500	O1W—H1W1	0.78 (2)
C11—C12	1.3962 (15)	O1W—H2W1	0.82 (2)
C11—H11A	0.9500	O2W—H2W2	0.86 (2)
C12—C13	1.3899 (15)	O2W—H1W2	0.98 (3)
C12—H12A	0.9500	O2W—H3W2	0.87 (2)
C13—C14	1.5128 (15)
N1—Co1—N2	165.60 (4)	C12—C11—H11A	120.0
N1—Co1—O4	116.74 (4)	C13—C12—C11	118.22 (10)
N2—Co1—O4	75.79 (3)	C13—C12—H12A	120.9
N1—Co1—O1	76.28 (3)	C11—C12—H12A	120.9
N2—Co1—O1	94.70 (3)	N2—C13—C12	121.33 (10)
O4—Co1—O1	102.06 (3)	N2—C13—C14	113.26 (9)
N1—Co1—O2	75.36 (3)	C12—C13—C14	125.30 (10)
N2—Co1—O2	114.18 (3)	O6—C14—O3	126.51 (10)
O4—Co1—O2	85.99 (3)	O6—C14—C13	118.22 (10)
O1—Co1—O2	151.12 (3)	O3—C14—C13	115.21 (9)
N1—Co1—O3	93.99 (3)	C22—O10—H1OA	110.1 (16)
N2—Co1—O3	74.89 (3)	C23—O12—H12B	113.6 (13)
O4—Co1—O3	148.33 (3)	C17—N8—C21	116.54 (10)
O1—Co1—O3	92.04 (3)	N8—C17—C18	123.48 (10)
O2—Co1—O3	95.24 (3)	N8—C17—C23	116.87 (9)
C6—N1—C2	120.70 (9)	C18—C17—C23	119.64 (10)
C6—N1—Co1	120.21 (7)	C19—C18—C17	118.96 (10)
C2—N1—Co1	118.84 (7)	C19—C18—H18A	120.5
C13—N2—C9	120.81 (9)	C17—C18—H18A	120.5
C13—N2—Co1	119.95 (7)	C20—C19—C18	118.44 (10)
C9—N2—Co1	119.22 (7)	C20—C19—H19A	120.8
C1—O1—Co1	114.51 (7)	C18—C19—H19A	120.8
C7—O2—Co1	115.16 (7)	C19—C20—C21	118.38 (10)
C14—O3—Co1	115.29 (7)	C19—C20—H20A	120.8
C8—O4—Co1	116.54 (7)	C21—C20—H20A	120.8
O8—C1—O1	127.20 (10)	N8—C21—C20	124.19 (10)
O8—C1—C2	116.62 (10)	N8—C21—C22	117.51 (10)
O1—C1—C2	116.17 (9)	C20—C21—C22	118.30 (10)
N1—C2—C3	121.32 (10)	O9—C22—O10	123.98 (11)
N1—C2—C1	113.46 (9)	O9—C22—C21	123.16 (11)
C3—C2—C1	125.22 (10)	O10—C22—C21	112.85 (10)
C2—C3—C4	118.37 (10)	O11—C23—O12	124.81 (10)
C2—C3—H3A	120.8	O11—C23—C17	124.43 (10)
C4—C3—H3A	120.8	O12—C23—C17	110.74 (9)
C3—C4—C5	120.10 (10)	C16—N3—H1N3	119.3 (13)
C3—C4—H4A	120.0	C16—N3—H2N3	117.9 (14)
C5—C4—H4A	120.0	H1N3—N3—H2N3	118.9 (19)
C6—C5—C4	117.77 (10)	C15—N4—H1N4	117.7 (14)
C6—C5—H5A	121.1	C15—N4—H2N4	120.0 (13)
C4—C5—H5A	121.1	H1N4—N4—H2N4	121.8 (19)
N1—C6—C5	121.75 (10)	C16—N5—N6	104.54 (9)
N1—C6—C7	112.49 (9)	C15—N6—N5	110.78 (9)
C5—C6—C7	125.75 (10)	C15—N6—H1N6	128.7 (12)
O7—C7—O2	125.78 (10)	N5—N6—H1N6	120.4 (12)
O7—C7—C6	117.92 (10)	C15—N7—C16	107.23 (9)
O2—C7—C6	116.27 (9)	C15—N7—H1N7	122.3 (13)
O4—C8—O5	126.31 (10)	C16—N7—H1N7	130.4 (13)
O4—C8—C9	116.39 (9)	N6—C15—N4	127.91 (11)
O5—C8—C9	117.30 (10)	N6—C15—N7	106.84 (10)
N2—C9—C10	121.80 (10)	N4—C15—N7	125.25 (10)
N2—C9—C8	111.81 (9)	N5—C16—N3	125.83 (11)
C10—C9—C8	126.33 (10)	N5—C16—N7	110.61 (10)
C9—C10—C11	117.79 (10)	N3—C16—N7	123.53 (10)
C9—C10—H10A	121.1	H1W1—O1W—H2W1	112 (2)
C11—C10—H10A	121.1	H2W2—O2W—H1W2	117 (2)
C10—C11—C12	120.03 (10)	H2W2—O2W—H3W2	107 (2)
C10—C11—H11A	120.0	H1W2—O2W—H3W2	114 (2)
N2—Co1—N1—C6	−129.11 (14)	Co1—O2—C7—O7	173.12 (9)
O4—Co1—N1—C6	81.84 (9)	Co1—O2—C7—C6	−4.72 (12)
O1—Co1—N1—C6	178.61 (9)	N1—C6—C7—O7	−170.09 (10)
O2—Co1—N1—C6	4.12 (8)	C5—C6—C7—O7	8.47 (17)
O3—Co1—N1—C6	−90.27 (8)	N1—C6—C7—O2	7.92 (14)
N2—Co1—N1—C2	45.17 (19)	C5—C6—C7—O2	−173.51 (11)
O4—Co1—N1—C2	−103.88 (8)	Co1—O4—C8—O5	−179.79 (9)
O1—Co1—N1—C2	−7.12 (8)	Co1—O4—C8—C9	1.30 (12)
O2—Co1—N1—C2	178.39 (9)	C13—N2—C9—C10	−0.75 (16)
O3—Co1—N1—C2	84.01 (8)	Co1—N2—C9—C10	177.15 (8)
N1—Co1—N2—C13	30.87 (19)	C13—N2—C9—C8	176.77 (9)
O4—Co1—N2—C13	−177.41 (9)	Co1—N2—C9—C8	−5.33 (12)
O1—Co1—N2—C13	81.32 (8)	O4—C8—C9—N2	2.47 (14)
O2—Co1—N2—C13	−98.53 (8)	O5—C8—C9—N2	−176.54 (10)
O3—Co1—N2—C13	−9.53 (8)	O4—C8—C9—C10	179.86 (10)
N1—Co1—N2—C9	−147.05 (13)	O5—C8—C9—C10	0.85 (16)
O4—Co1—N2—C9	4.67 (8)	N2—C9—C10—C11	−0.58 (16)
O1—Co1—N2—C9	−96.60 (8)	C8—C9—C10—C11	−177.72 (10)
O2—Co1—N2—C9	83.55 (8)	C9—C10—C11—C12	0.86 (16)
O3—Co1—N2—C9	172.55 (9)	C10—C11—C12—C13	0.11 (17)
N1—Co1—O1—C1	7.60 (8)	C9—N2—C13—C12	1.79 (16)
N2—Co1—O1—C1	−161.02 (8)	Co1—N2—C13—C12	−176.09 (8)
O4—Co1—O1—C1	122.53 (8)	C9—N2—C13—C14	−174.64 (9)
O2—Co1—O1—C1	18.69 (12)	Co1—N2—C13—C14	7.48 (12)
O3—Co1—O1—C1	−86.02 (8)	C11—C12—C13—N2	−1.46 (17)
N1—Co1—O2—C7	0.71 (8)	C11—C12—C13—C14	174.52 (10)
N2—Co1—O2—C7	169.25 (8)	Co1—O3—C14—O6	172.81 (10)
O4—Co1—O2—C7	−118.28 (8)	Co1—O3—C14—C13	−10.06 (12)
O1—Co1—O2—C7	−10.43 (12)	N2—C13—C14—O6	179.76 (10)
O3—Co1—O2—C7	93.47 (8)	C12—C13—C14—O6	3.49 (17)
N1—Co1—O3—C14	−160.07 (8)	N2—C13—C14—O3	2.37 (14)
N2—Co1—O3—C14	10.63 (8)	C12—C13—C14—O3	−173.89 (11)
O4—Co1—O3—C14	33.44 (11)	C21—N8—C17—C18	1.17 (16)
O1—Co1—O3—C14	−83.69 (8)	C21—N8—C17—C23	−178.06 (10)
O2—Co1—O3—C14	124.29 (8)	N8—C17—C18—C19	−0.37 (18)
N1—Co1—O4—C8	169.32 (8)	C23—C17—C18—C19	178.84 (10)
N2—Co1—O4—C8	−3.10 (8)	C17—C18—C19—C20	−0.96 (17)
O1—Co1—O4—C8	88.76 (8)	C18—C19—C20—C21	1.41 (17)
O2—Co1—O4—C8	−119.28 (8)	C17—N8—C21—C20	−0.67 (17)
O3—Co1—O4—C8	−25.80 (12)	C17—N8—C21—C22	178.97 (10)
Co1—O1—C1—O8	171.75 (10)	C19—C20—C21—N8	−0.61 (18)
Co1—O1—C1—C2	−6.90 (12)	C19—C20—C21—C22	179.75 (10)
C6—N1—C2—C3	0.73 (16)	N8—C21—C22—O9	179.71 (11)
Co1—N1—C2—C3	−173.52 (8)	C20—C21—C22—O9	−0.62 (18)
C6—N1—C2—C1	−179.91 (9)	N8—C21—C22—O10	−1.23 (15)
Co1—N1—C2—C1	5.85 (12)	C20—C21—C22—O10	178.43 (10)
O8—C1—C2—N1	−177.62 (10)	N8—C17—C23—O11	−8.97 (17)
O1—C1—C2—N1	1.18 (14)	C18—C17—C23—O11	171.78 (12)
O8—C1—C2—C3	1.72 (17)	N8—C17—C23—O12	170.01 (10)
O1—C1—C2—C3	−179.48 (11)	C18—C17—C23—O12	−9.25 (15)
N1—C2—C3—C4	−0.38 (17)	C16—N5—N6—C15	−0.68 (13)
C1—C2—C3—C4	−179.67 (10)	N5—N6—C15—N4	179.92 (12)
C2—C3—C4—C5	−0.34 (17)	N5—N6—C15—N7	0.39 (13)
C3—C4—C5—C6	0.70 (17)	C16—N7—C15—N6	0.05 (13)
C2—N1—C6—C5	−0.35 (16)	C16—N7—C15—N4	−179.50 (11)
Co1—N1—C6—C5	173.82 (8)	N6—N5—C16—N3	178.62 (11)
C2—N1—C6—C7	178.28 (9)	N6—N5—C16—N7	0.70 (12)
Co1—N1—C6—C7	−7.55 (12)	C15—N7—C16—N5	−0.49 (13)
C4—C5—C6—N1	−0.37 (17)	C15—N7—C16—N3	−178.47 (11)
C4—C5—C6—C7	−178.81 (10)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1N3···O10i	0.841 (19)	2.249 (18)	3.0304 (15)	154.5 (17)
N3—H1N3···N8i	0.841 (19)	2.47 (2)	3.1379 (15)	136.5 (16)
N3—H2N3···O11i	0.86 (2)	2.28 (2)	2.9563 (15)	135.7 (17)
N4—H1N4···O2	0.85 (2)	2.072 (19)	2.9084 (14)	169 (2)
N4—H2N4···O1W	0.85 (2)	1.96 (2)	2.8057 (16)	172 (2)
N6—H1N6···O3ii	0.877 (18)	1.870 (18)	2.7368 (12)	169.7 (16)
N7—H1N7···O7	0.85 (2)	1.89 (2)	2.7245 (13)	167 (2)
O10—H1OA···O7i	0.79 (2)	1.86 (2)	2.5775 (13)	152 (3)
O1W—H1W1···O6iii	0.78 (2)	2.06 (2)	2.8315 (14)	172 (2)
O1W—H2W1···O1ii	0.82 (3)	2.23 (3)	2.8901 (14)	138 (2)
O2W—H2W2···O8iv	0.87 (3)	1.67 (2)	2.5279 (13)	170 (2)
O2W—H1W2···O5v	0.98 (3)	1.48 (3)	2.4622 (13)	177 (3)
O2W—H3W2···O6ii	0.87 (2)	1.71 (2)	2.5746 (13)	174 (2)
O12—H12B···N5vi	0.89 (2)	1.76 (2)	2.6303 (14)	169 (2)
C3—H3A···O9vii	0.95	2.52	3.1725 (14)	126
C5—H5A···O9i	0.95	2.59	3.5380 (15)	175
C10—H10A···O1viii	0.95	2.38	3.2669 (14)	156
C19—H19A···O2W	0.95	2.50	3.4269 (15)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H1N3⋯O10i	0.841 (19)	2.249 (18)	3.0304 (15)	154.5 (17)
N3—H1N3⋯N8i	0.841 (19)	2.47 (2)	3.1379 (15)	136.5 (16)
N3—H2N3⋯O11i	0.86 (2)	2.28 (2)	2.9563 (15)	135.7 (17)
N4—H1N4⋯O2	0.85 (2)	2.072 (19)	2.9084 (14)	169 (2)
N4—H2N4⋯O1W	0.85 (2)	1.96 (2)	2.8057 (16)	172 (2)
N6—H1N6⋯O3ii	0.877 (18)	1.870 (18)	2.7368 (12)	169.7 (16)
N7—H1N7⋯O7	0.85 (2)	1.89 (2)	2.7245 (13)	167 (2)
O10—H1OA⋯O7i	0.79 (2)	1.86 (2)	2.5775 (13)	152 (3)
O1W—H1W1⋯O6iii	0.78 (2)	2.06 (2)	2.8315 (14)	172 (2)
O1W—H2W1⋯O1ii	0.82 (3)	2.23 (3)	2.8901 (14)	138 (2)
O2W—H2W2⋯O8iv	0.87 (3)	1.67 (2)	2.5279 (13)	170 (2)
O2W—H1W2⋯O5v	0.98 (3)	1.48 (3)	2.4622 (13)	177 (3)
O2W—H3W2⋯O6ii	0.87 (2)	1.71 (2)	2.5746 (13)	174 (2)
O12—H12B⋯N5vi	0.89 (2)	1.76 (2)	2.6303 (14)	169 (2)
C3—H3A⋯O9vii	0.95	2.52	3.1725 (14)	126
C5—H5A⋯O9i	0.95	2.59	3.5380 (15)	175
C10—H10A⋯O1viii	0.95	2.38	3.2669 (14)	156
C19—H19A⋯O2W	0.95	2.50	3.4269 (15)	165

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