Benzene-1,3-diammonium bis-(pyridine-2,6-dicarboxyl-ato-κO,N,O)cobaltate(II) penta-hydrate.

In the title compound, (C(6)H(10)N(2))[Co(C(7)H(3)NO(4))(2)]·5H(2)O, the Co(II) ion is six-coordinated in an N(2)O(4) environment by two pyridine-2,6-dicarboxyl-ate (pydc) ligands, having a distorted octa-hedral geometry. The crystal packing is stabilized by inter-molecular N-H⋯O, O-H⋯O and weak C-H⋯O hydrogen bonds. There are also π-π inter-actions between the pyridine rings of the pydc ligands and between the pydc ligands and the benzene-1,3-diammonium cations, with centroid-centroid distances of 3.4575 (15) and 3.7521 (15) Å.

Related literature

For general background to proton-transfer compounds, see: Aghabozorg et al. (2008 ▶). For related structures, see: Beatty et al. (2002 ▶); Dobrzycki & Woźniak (2008 ▶); Imaz et al. (2007 ▶); Pasdar et al. (2010 ▶, 2011a ▶,b ▶).

Experimental

Crystal data

(C6H10N2)[Co(C7H3NO4)2]·5H2O

M = 589.38

Monoclinic,

a = 7.5236 (2) Å

b = 18.0200 (7) Å

c = 18.7122 (6) Å

β = 100.883 (2)°

V = 2491.29 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.76 mm−1

T = 298 K

0.50 × 0.15 × 0.10 mm

Data collection

Stoe IPDS-2 diffractometer

19874 measured reflections

6702 independent reflections

5366 reflections with I > 2σ(I)

R int = 0.064

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.113

S = 1.21

6702 reflections

407 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.34 e Å−3

Δρmin = −0.32 e Å−3

Data collection: X-AREA (Stoe & Cie, 2005 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811009858/hy2407sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811009858/hy2407Isup2.hkl

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

(C6H10N2)[Co(C7H3NO4)2]·5H2O	F(000) = 1220
Mr = 589.38	Dx = 1.571 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6702 reflections
a = 7.5236 (2) Å	θ = 2.2–29.2°
b = 18.0200 (7) Å	µ = 0.76 mm−1
c = 18.7122 (6) Å	T = 298 K
β = 100.883 (2)°	Needle, dark pink
V = 2491.29 (14) Å3	0.50 × 0.15 × 0.10 mm
Z = 4

Stoe IPDS-2 diffractometer	5366 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.064
graphite	θmax = 29.2°, θmin = 2.2°
ω scans	h = −10→9
19874 measured reflections	k = −23→24
6702 independent 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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113	H atoms treated by a mixture of independent and constrained refinement
S = 1.21	w = 1/[σ2(Fo2) + (0.031P)2 + 1.7282P] where P = (Fo2 + 2Fc2)/3
6702 reflections	(Δ/σ)max = 0.007
407 parameters	Δρmax = 0.34 e Å−3
2 restraints	Δρmin = −0.32 e Å−3

	x	y	z	Uiso*/Ueq
Co1	0.64449 (5)	0.982592 (19)	0.312577 (16)	0.02479 (9)
O1	0.8779 (3)	1.03503 (13)	0.28454 (10)	0.0426 (5)
O2	1.0026 (3)	1.06589 (13)	0.19026 (12)	0.0481 (6)
O3	0.4033 (3)	0.91494 (11)	0.28828 (9)	0.0341 (4)
O4	0.2123 (3)	0.86302 (14)	0.19579 (11)	0.0471 (5)
O5	0.4980 (3)	1.08443 (11)	0.31941 (10)	0.0355 (4)
O6	0.4177 (3)	1.16437 (10)	0.39852 (11)	0.0348 (4)
O7	0.8000 (3)	0.88934 (11)	0.35988 (9)	0.0367 (4)
O8	0.9307 (3)	0.83948 (12)	0.46576 (11)	0.0448 (5)
O9	0.3372 (3)	0.77720 (13)	0.34605 (11)	0.0393 (5)
O10	0.5258 (5)	0.72787 (18)	0.48332 (16)	0.0614 (7)
O11	0.8434 (5)	0.69320 (18)	0.43693 (16)	0.0659 (7)
O12	0.3223 (4)	0.5943 (2)	0.42544 (17)	0.0670 (8)
O13	0.0351 (4)	0.65086 (15)	0.32207 (15)	0.0519 (6)
N1	0.6128 (3)	0.96490 (11)	0.20453 (10)	0.0251 (4)
N2	0.6870 (3)	1.00350 (10)	0.42057 (10)	0.0220 (4)
N3	0.9659 (3)	0.80230 (14)	0.27389 (12)	0.0292 (4)
N4	0.3688 (3)	0.68621 (13)	0.22490 (13)	0.0282 (4)
C1	0.7387 (4)	0.99011 (14)	0.16927 (13)	0.0288 (5)
C2	0.7267 (4)	0.97588 (17)	0.09568 (14)	0.0392 (6)
H2	0.8153	0.9927	0.0711	0.047*
C3	0.5791 (4)	0.93595 (17)	0.05974 (14)	0.0404 (7)
H3	0.5683	0.9257	0.0104	0.048*
C4	0.4476 (4)	0.91124 (16)	0.09695 (13)	0.0356 (6)
H4	0.3470	0.8851	0.0731	0.043*
C5	0.4702 (3)	0.92658 (14)	0.17044 (12)	0.0261 (5)
C6	0.8870 (4)	1.03362 (15)	0.21823 (14)	0.0327 (5)
C7	0.3483 (3)	0.89943 (14)	0.22113 (13)	0.0290 (5)
C8	0.6188 (3)	1.06555 (13)	0.44373 (12)	0.0242 (4)
C9	0.6530 (4)	1.08338 (15)	0.51711 (13)	0.0301 (5)
H9	0.6071	1.1268	0.5334	0.036*
C10	0.7571 (4)	1.03510 (15)	0.56585 (13)	0.0309 (5)
H10	0.7816	1.0462	0.6153	0.037*
C11	0.8246 (3)	0.97036 (14)	0.54083 (12)	0.0266 (5)
H11	0.8943	0.9375	0.5728	0.032*
C12	0.7848 (3)	0.95620 (13)	0.46633 (12)	0.0228 (4)
C13	0.5029 (3)	1.10953 (13)	0.38304 (13)	0.0261 (5)
C14	0.8452 (3)	0.88883 (14)	0.42920 (13)	0.0277 (5)
C15	0.8107 (3)	0.77539 (13)	0.22120 (12)	0.0242 (4)
C16	0.8140 (4)	0.77813 (15)	0.14768 (13)	0.0304 (5)
H16	0.9120	0.7987	0.1310	0.036*
C17	0.6676 (4)	0.74947 (17)	0.09941 (13)	0.0359 (6)
H17	0.6678	0.7504	0.0497	0.043*
C18	0.5211 (4)	0.71944 (15)	0.12409 (13)	0.0312 (5)
H18	0.4236	0.7002	0.0913	0.037*
C19	0.5212 (3)	0.71837 (13)	0.19752 (13)	0.0250 (5)
C20	0.6661 (3)	0.74587 (14)	0.24743 (12)	0.0266 (5)
H20	0.6659	0.7445	0.2971	0.032*
H3A	1.041 (5)	0.8267 (19)	0.2526 (18)	0.042 (9)*
H4A	0.342 (5)	0.714 (2)	0.261 (2)	0.057 (11)*
H9A	0.381 (5)	0.819 (2)	0.3366 (18)	0.043 (9)*
H10A	0.543 (7)	0.755 (3)	0.519 (3)	0.093 (18)*
H11A	0.903 (7)	0.741 (3)	0.439 (3)	0.087 (16)*
H12A	0.387 (9)	0.634 (4)	0.448 (3)	0.12 (2)*
H13A	0.125 (6)	0.633 (3)	0.352 (3)	0.11 (2)*
H3B	0.929 (5)	0.8373 (19)	0.3069 (18)	0.044 (9)*
H4B	0.403 (5)	0.642 (2)	0.2465 (19)	0.052 (10)*
H9B	0.385 (5)	0.763 (2)	0.3831 (17)	0.055 (12)*
H10B	0.624 (7)	0.719 (3)	0.475 (2)	0.068 (15)*
H11B	0.886 (7)	0.671 (3)	0.403 (3)	0.081 (15)*
H12B	0.380 (7)	0.580 (3)	0.401 (3)	0.074 (16)*
H13B	0.033 (7)	0.624 (3)	0.289 (3)	0.089 (17)*
H3C	1.035 (5)	0.762 (2)	0.301 (2)	0.057 (11)*
H4C	0.277 (5)	0.6805 (19)	0.1891 (19)	0.045 (9)*

	U11	U22	U33	U12	U13	U23
Co1	0.02959 (17)	0.02648 (16)	0.01790 (13)	−0.00151 (14)	0.00348 (11)	−0.00162 (12)
O1	0.0403 (11)	0.0565 (14)	0.0311 (9)	−0.0213 (10)	0.0069 (8)	−0.0076 (9)
O2	0.0504 (13)	0.0507 (13)	0.0487 (12)	−0.0263 (11)	0.0232 (10)	−0.0087 (10)
O3	0.0383 (10)	0.0402 (10)	0.0258 (8)	−0.0118 (8)	0.0109 (7)	−0.0033 (7)
O4	0.0383 (11)	0.0640 (15)	0.0388 (10)	−0.0237 (10)	0.0065 (9)	−0.0065 (10)
O5	0.0451 (11)	0.0319 (10)	0.0269 (8)	0.0085 (8)	0.0001 (8)	0.0007 (7)
O6	0.0304 (10)	0.0303 (10)	0.0425 (10)	0.0070 (8)	0.0039 (8)	−0.0020 (8)
O7	0.0486 (12)	0.0358 (10)	0.0244 (8)	0.0155 (9)	0.0036 (8)	−0.0048 (7)
O8	0.0575 (14)	0.0389 (11)	0.0366 (10)	0.0198 (10)	0.0052 (9)	0.0045 (9)
O9	0.0457 (12)	0.0370 (12)	0.0338 (10)	−0.0053 (9)	0.0035 (9)	−0.0008 (9)
O10	0.0624 (19)	0.0697 (19)	0.0494 (14)	0.0069 (15)	0.0035 (13)	−0.0104 (13)
O11	0.082 (2)	0.0566 (17)	0.0617 (17)	0.0052 (15)	0.0205 (15)	−0.0063 (14)
O12	0.0659 (19)	0.084 (2)	0.0579 (16)	0.0049 (17)	0.0296 (15)	−0.0025 (15)
O13	0.0587 (16)	0.0464 (14)	0.0483 (13)	0.0015 (11)	0.0047 (12)	−0.0124 (11)
N1	0.0312 (11)	0.0235 (10)	0.0206 (8)	−0.0037 (8)	0.0054 (7)	−0.0010 (7)
N2	0.0222 (9)	0.0237 (10)	0.0203 (8)	−0.0007 (7)	0.0045 (7)	−0.0012 (7)
N3	0.0210 (10)	0.0362 (12)	0.0301 (10)	−0.0029 (9)	0.0036 (8)	−0.0084 (9)
N4	0.0239 (10)	0.0273 (11)	0.0331 (11)	−0.0015 (8)	0.0048 (9)	−0.0008 (9)
C1	0.0346 (13)	0.0261 (12)	0.0271 (11)	−0.0048 (10)	0.0093 (9)	0.0001 (9)
C2	0.0521 (17)	0.0404 (15)	0.0294 (12)	−0.0096 (13)	0.0184 (11)	−0.0011 (11)
C3	0.0572 (19)	0.0425 (16)	0.0224 (11)	−0.0083 (13)	0.0099 (11)	−0.0042 (11)
C4	0.0434 (15)	0.0367 (14)	0.0247 (11)	−0.0083 (12)	0.0009 (10)	−0.0068 (10)
C5	0.0276 (12)	0.0261 (12)	0.0242 (10)	−0.0022 (9)	0.0036 (9)	0.0001 (9)
C6	0.0352 (13)	0.0302 (13)	0.0346 (12)	−0.0081 (10)	0.0118 (10)	−0.0034 (10)
C7	0.0279 (12)	0.0311 (13)	0.0282 (11)	−0.0048 (10)	0.0058 (9)	−0.0014 (10)
C8	0.0227 (11)	0.0241 (11)	0.0263 (10)	−0.0014 (8)	0.0056 (8)	−0.0023 (9)
C9	0.0322 (13)	0.0304 (12)	0.0285 (11)	−0.0010 (10)	0.0077 (10)	−0.0102 (10)
C10	0.0337 (13)	0.0384 (14)	0.0204 (10)	−0.0044 (10)	0.0044 (9)	−0.0079 (9)
C11	0.0249 (11)	0.0335 (13)	0.0212 (10)	−0.0012 (9)	0.0036 (8)	0.0022 (9)
C12	0.0205 (10)	0.0271 (11)	0.0213 (10)	0.0000 (8)	0.0053 (8)	0.0002 (8)
C13	0.0223 (11)	0.0249 (11)	0.0307 (11)	−0.0024 (9)	0.0036 (9)	−0.0003 (9)
C14	0.0277 (12)	0.0284 (12)	0.0266 (11)	0.0023 (9)	0.0043 (9)	0.0008 (9)
C15	0.0194 (10)	0.0261 (11)	0.0263 (10)	0.0018 (9)	0.0022 (8)	−0.0058 (9)
C16	0.0287 (12)	0.0345 (13)	0.0295 (12)	−0.0015 (10)	0.0094 (10)	−0.0021 (10)
C17	0.0377 (15)	0.0482 (16)	0.0219 (11)	−0.0040 (12)	0.0060 (10)	−0.0036 (11)
C18	0.0298 (13)	0.0331 (13)	0.0284 (11)	−0.0040 (10)	−0.0004 (9)	−0.0074 (10)
C19	0.0200 (11)	0.0238 (11)	0.0312 (11)	0.0007 (9)	0.0044 (9)	−0.0027 (9)
C20	0.0252 (12)	0.0310 (12)	0.0235 (10)	−0.0004 (9)	0.0042 (9)	−0.0035 (9)

Co1—N1	2.0160 (19)	N4—C19	1.461 (3)
Co1—N2	2.0209 (18)	N4—H4A	0.89 (4)
Co1—O7	2.1414 (19)	N4—H4B	0.90 (4)
Co1—O1	2.145 (2)	N4—H4C	0.88 (4)
Co1—O5	2.1570 (19)	C1—C2	1.387 (3)
Co1—O3	2.1621 (19)	C1—C6	1.521 (4)
O1—C6	1.256 (3)	C2—C3	1.386 (4)
O2—C6	1.241 (3)	C2—H2	0.9300
O3—C7	1.277 (3)	C3—C4	1.387 (4)
O4—C7	1.233 (3)	C3—H3	0.9300
O5—C13	1.268 (3)	C4—C5	1.381 (3)
O6—C13	1.242 (3)	C4—H4	0.9300
O7—C14	1.277 (3)	C5—C7	1.519 (3)
O8—C14	1.228 (3)	C8—C9	1.386 (3)
O9—H9A	0.86 (4)	C8—C13	1.518 (3)
O9—H9B	0.76 (3)	C9—C10	1.390 (4)
O10—H10A	0.81 (6)	C9—H9	0.9300
O10—H10B	0.80 (5)	C10—C11	1.389 (4)
O11—H11A	0.97 (5)	C10—H10	0.9300
O11—H11B	0.86 (5)	C11—C12	1.393 (3)
O12—H12A	0.93 (7)	C11—H11	0.9300
O12—H12B	0.73 (5)	C12—C14	1.511 (3)
O13—H13A	0.86 (3)	C15—C16	1.381 (3)
O13—H13B	0.78 (5)	C15—C20	1.382 (3)
N1—C5	1.332 (3)	C16—C17	1.386 (4)
N1—C1	1.333 (3)	C16—H16	0.9300
N2—C12	1.328 (3)	C17—C18	1.383 (4)
N2—C8	1.336 (3)	C17—H17	0.9300
N3—C15	1.462 (3)	C18—C19	1.374 (3)
N3—H3A	0.87 (4)	C18—H18	0.9300
N3—H3B	0.96 (4)	C19—C20	1.386 (3)
N3—H3C	0.98 (4)	C20—H20	0.9300
N1—Co1—N2	177.16 (8)	C5—C4—C3	118.0 (2)
N1—Co1—O7	104.03 (7)	C5—C4—H4	121.0
N2—Co1—O7	76.23 (7)	C3—C4—H4	121.0
N1—Co1—O1	76.81 (8)	N1—C5—C4	121.1 (2)
N2—Co1—O1	100.37 (7)	N1—C5—C7	113.2 (2)
O7—Co1—O1	92.18 (9)	C4—C5—C7	125.6 (2)
N1—Co1—O5	103.23 (8)	O2—C6—O1	125.5 (3)
N2—Co1—O5	76.60 (7)	O2—C6—C1	118.7 (2)
O7—Co1—O5	152.70 (7)	O1—C6—C1	115.8 (2)
O1—Co1—O5	95.22 (9)	O4—C7—O3	125.9 (2)
N1—Co1—O3	76.36 (7)	O4—C7—C5	119.1 (2)
N2—Co1—O3	106.48 (7)	O3—C7—C5	115.0 (2)
O7—Co1—O3	90.92 (8)	N2—C8—C9	120.3 (2)
O1—Co1—O3	152.93 (7)	N2—C8—C13	113.31 (19)
O5—Co1—O3	94.25 (8)	C9—C8—C13	126.4 (2)
C6—O1—Co1	115.64 (17)	C8—C9—C10	118.7 (2)
C7—O3—Co1	115.67 (16)	C8—C9—H9	120.6
C13—O5—Co1	115.76 (16)	C10—C9—H9	120.6
C14—O7—Co1	116.43 (16)	C11—C10—C9	120.1 (2)
H9A—O9—H9B	111 (4)	C11—C10—H10	120.0
H10A—O10—H10B	106 (5)	C9—C10—H10	120.0
H11A—O11—H11B	102 (4)	C10—C11—C12	117.9 (2)
H12A—O12—H12B	104 (5)	C10—C11—H11	121.0
H13A—O13—H13B	100 (5)	C12—C11—H11	121.0
C5—N1—C1	121.5 (2)	N2—C12—C11	121.1 (2)
C5—N1—Co1	119.62 (16)	N2—C12—C14	113.42 (19)
C1—N1—Co1	118.82 (16)	C11—C12—C14	125.5 (2)
C12—N2—C8	121.87 (19)	O6—C13—O5	125.3 (2)
C12—N2—Co1	119.28 (15)	O6—C13—C8	119.3 (2)
C8—N2—Co1	118.84 (15)	O5—C13—C8	115.3 (2)
C15—N3—H3A	111 (2)	O8—C14—O7	125.6 (2)
C15—N3—H3B	111 (2)	O8—C14—C12	119.8 (2)
H3A—N3—H3B	105 (3)	O7—C14—C12	114.6 (2)
C15—N3—H3C	112 (2)	C16—C15—C20	122.1 (2)
H3A—N3—H3C	107 (3)	C16—C15—N3	119.8 (2)
H3B—N3—H3C	110 (3)	C20—C15—N3	118.1 (2)
C19—N4—H4A	110 (3)	C15—C16—C17	118.3 (2)
C19—N4—H4B	109 (2)	C15—C16—H16	120.8
H4A—N4—H4B	104 (3)	C17—C16—H16	120.8
C19—N4—H4C	110 (2)	C18—C17—C16	120.9 (2)
H4A—N4—H4C	112 (3)	C18—C17—H17	119.5
H4B—N4—H4C	111 (3)	C16—C17—H17	119.5
N1—C1—C2	120.6 (2)	C19—C18—C17	119.3 (2)
N1—C1—C6	112.8 (2)	C19—C18—H18	120.4
C2—C1—C6	126.6 (2)	C17—C18—H18	120.4
C3—C2—C1	118.3 (2)	C18—C19—C20	121.4 (2)
C3—C2—H2	120.9	C18—C19—N4	120.3 (2)
C1—C2—H2	120.9	C20—C19—N4	118.3 (2)
C2—C3—C4	120.4 (2)	C15—C20—C19	118.0 (2)
C2—C3—H3	119.8	C15—C20—H20	121.0
C4—C3—H3	119.8	C19—C20—H20	121.0
N1—Co1—O1—C6	2.1 (2)	C3—C4—C5—C7	−175.3 (3)
N2—Co1—O1—C6	−177.6 (2)	Co1—O1—C6—O2	173.7 (2)
O7—Co1—O1—C6	106.0 (2)	Co1—O1—C6—C1	−4.3 (3)
O5—Co1—O1—C6	−100.3 (2)	N1—C1—C6—O2	−173.2 (3)
O3—Co1—O1—C6	9.7 (3)	C2—C1—C6—O2	6.8 (4)
N1—Co1—O3—C7	−3.76 (19)	N1—C1—C6—O1	5.0 (4)
N2—Co1—O3—C7	176.12 (18)	C2—C1—C6—O1	−174.9 (3)
O7—Co1—O3—C7	−107.98 (19)	Co1—O3—C7—O4	−178.5 (2)
O1—Co1—O3—C7	−11.4 (3)	Co1—O3—C7—C5	4.3 (3)
O5—Co1—O3—C7	98.85 (19)	N1—C5—C7—O4	−179.7 (3)
N1—Co1—O5—C13	−177.44 (18)	C4—C5—C7—O4	−3.2 (4)
N2—Co1—O5—C13	−0.35 (18)	N1—C5—C7—O3	−2.3 (3)
O7—Co1—O5—C13	5.3 (3)	C4—C5—C7—O3	174.2 (3)
O1—Co1—O5—C13	−99.79 (19)	C12—N2—C8—C9	1.8 (3)
O3—Co1—O5—C13	105.59 (19)	Co1—N2—C8—C9	−176.81 (18)
N1—Co1—O7—C14	177.36 (19)	C12—N2—C8—C13	−176.8 (2)
N2—Co1—O7—C14	0.26 (19)	Co1—N2—C8—C13	4.6 (3)
O1—Co1—O7—C14	100.4 (2)	N2—C8—C9—C10	−0.9 (4)
O5—Co1—O7—C14	−5.4 (3)	C13—C8—C9—C10	177.6 (2)
O3—Co1—O7—C14	−106.5 (2)	C8—C9—C10—C11	−0.1 (4)
O7—Co1—N1—C5	89.93 (19)	C9—C10—C11—C12	0.1 (4)
O1—Co1—N1—C5	178.9 (2)	C8—N2—C12—C11	−1.7 (3)
O5—Co1—N1—C5	−88.78 (19)	Co1—N2—C12—C11	176.86 (17)
O3—Co1—N1—C5	2.43 (18)	C8—N2—C12—C14	178.6 (2)
O7—Co1—N1—C1	−88.0 (2)	Co1—N2—C12—C14	−2.8 (3)
O1—Co1—N1—C1	0.90 (19)	C10—C11—C12—N2	0.7 (4)
O5—Co1—N1—C1	93.24 (19)	C10—C11—C12—C14	−179.7 (2)
O3—Co1—N1—C1	−175.5 (2)	Co1—O5—C13—O6	−174.9 (2)
O7—Co1—N2—C12	1.51 (17)	Co1—O5—C13—C8	2.7 (3)
O1—Co1—N2—C12	−88.20 (18)	N2—C8—C13—O6	173.0 (2)
O5—Co1—N2—C12	178.85 (19)	C9—C8—C13—O6	−5.5 (4)
O3—Co1—N2—C12	88.34 (18)	N2—C8—C13—O5	−4.8 (3)
O7—Co1—N2—C8	−179.87 (19)	C9—C8—C13—O5	176.7 (2)
O1—Co1—N2—C8	90.42 (18)	Co1—O7—C14—O8	178.4 (2)
O5—Co1—N2—C8	−2.53 (17)	Co1—O7—C14—C12	−1.7 (3)
O3—Co1—N2—C8	−93.04 (18)	N2—C12—C14—O8	−177.2 (2)
C5—N1—C1—C2	−1.2 (4)	C11—C12—C14—O8	3.1 (4)
Co1—N1—C1—C2	176.7 (2)	N2—C12—C14—O7	2.9 (3)
C5—N1—C1—C6	178.8 (2)	C11—C12—C14—O7	−176.7 (2)
Co1—N1—C1—C6	−3.2 (3)	C20—C15—C16—C17	−0.7 (4)
N1—C1—C2—C3	1.0 (4)	N3—C15—C16—C17	177.5 (2)
C6—C1—C2—C3	−179.0 (3)	C15—C16—C17—C18	0.5 (4)
C1—C2—C3—C4	0.1 (5)	C16—C17—C18—C19	0.2 (4)
C2—C3—C4—C5	−1.1 (5)	C17—C18—C19—C20	−0.9 (4)
C1—N1—C5—C4	0.2 (4)	C17—C18—C19—N4	−179.3 (2)
Co1—N1—C5—C4	−177.8 (2)	C16—C15—C20—C19	0.1 (4)
C1—N1—C5—C7	176.9 (2)	N3—C15—C20—C19	−178.1 (2)
Co1—N1—C5—C7	−1.0 (3)	C18—C19—C20—C15	0.7 (4)
C3—C4—C5—N1	1.0 (4)	N4—C19—C20—C15	179.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O3i	0.93	2.57	3.311 (3)	136
C18—H18···O8ii	0.93	2.47	3.099 (3)	125
O9—H9A···O3	0.86 (4)	1.97 (4)	2.789 (3)	160 (3)
O9—H9B···O10	0.76 (3)	2.07 (3)	2.833 (4)	176 (4)
O10—H10A···O6i	0.81 (6)	2.10 (6)	2.913 (4)	173 (5)
O10—H10B···O11	0.80 (5)	1.97 (5)	2.764 (5)	170 (5)
O11—H11A···O8	0.97 (5)	1.84 (5)	2.746 (4)	153 (4)
O11—H11B···O13iii	0.86 (5)	2.08 (5)	2.907 (4)	161 (5)
O12—H12A···O10	0.93 (7)	2.03 (7)	2.946 (5)	171 (5)
O12—H12B···O2iv	0.73 (5)	2.09 (5)	2.786 (4)	161 (5)
O13—H13A···O12	0.86 (3)	1.95 (3)	2.805 (4)	176 (5)
O13—H13B···O5v	0.78 (5)	2.13 (5)	2.873 (3)	161 (5)
N3—H3A···O4iii	0.87 (4)	1.93 (4)	2.791 (3)	169 (3)
N3—H3B···O7	0.96 (4)	1.78 (4)	2.714 (3)	163 (3)
N3—H3C···O13iii	0.98 (4)	2.04 (4)	2.890 (4)	144 (3)
N3—H3C···O9iii	0.98 (4)	2.29 (4)	2.899 (3)	120 (3)
N4—H4A···O9	0.89 (4)	1.97 (4)	2.844 (3)	168 (4)
N4—H4B···O2iv	0.90 (4)	1.87 (4)	2.752 (3)	166 (3)
N4—H4C···O6v	0.88 (4)	2.00 (4)	2.873 (3)	175 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10⋯O3i	0.93	2.57	3.311 (3)	136
C18—H18⋯O8ii	0.93	2.47	3.099 (3)	125
O9—H9A⋯O3	0.86 (4)	1.97 (4)	2.789 (3)	160 (3)
O9—H9B⋯O10	0.76 (3)	2.07 (3)	2.833 (4)	176 (4)
O10—H10A⋯O6i	0.81 (6)	2.10 (6)	2.913 (4)	173 (5)
O10—H10B⋯O11	0.80 (5)	1.97 (5)	2.764 (5)	170 (5)
O11—H11A⋯O8	0.97 (5)	1.84 (5)	2.746 (4)	153 (4)
O11—H11B⋯O13iii	0.86 (5)	2.08 (5)	2.907 (4)	161 (5)
O12—H12A⋯O10	0.93 (7)	2.03 (7)	2.946 (5)	171 (5)
O12—H12B⋯O2iv	0.73 (5)	2.09 (5)	2.786 (4)	161 (5)
O13—H13A⋯O12	0.86 (3)	1.95 (3)	2.805 (4)	176 (5)
O13—H13B⋯O5v	0.78 (5)	2.13 (5)	2.873 (3)	161 (5)
N3—H3A⋯O4iii	0.87 (4)	1.93 (4)	2.791 (3)	169 (3)
N3—H3B⋯O7	0.96 (4)	1.78 (4)	2.714 (3)	163 (3)
N3—H3C⋯O13iii	0.98 (4)	2.04 (4)	2.890 (4)	144 (3)
N3—H3C⋯O9iii	0.98 (4)	2.29 (4)	2.899 (3)	120 (3)
N4—H4A⋯O9	0.89 (4)	1.97 (4)	2.844 (3)	168 (4)
N4—H4B⋯O2iv	0.90 (4)	1.87 (4)	2.752 (3)	166 (3)
N4—H4C⋯O6v	0.88 (4)	2.00 (4)	2.873 (3)	175 (3)

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