(μ-4,4'-Bipyridine-κN:N')bis-[triaqua-(4,4'-bipyridine-κN)(3-nitro-phthalato-κO)cobalt(II)].

The title binuclear complex, [Co(2)(C(8)H(3)NO(6))(2)(C(10)H(8)N(2))(3)(H(2)O)(6)], has been synthesized hydro-thermally from 3-nitro-phthalic acid (H(2)NPA), Co(NO(3))(2)·6H(2)O and 4,4'-bipyridine (4,4'-bipy). The mol-ecule of the complex occupies a special position on an inversion centre. The Co(II) atom has a slightly distorted octa-hedral environment formed by two N atoms from two 4,4'-bipy ligands, one carboxyl-ate O atom from NPA, and three O atoms of water mol-ecules. An extensive O-H⋯O and N-H⋯O hydrogen-bonding system links mol-ecules of the complex into a three-dimensional network.

Related literature

For background to metal-involved supra­molecular compounds, see: n class="Chemical">Noro (2004 ▶); Yaghi et al. (2003 ▶); Rao et al. (2004 ▶); Huang et al. (2004 ▶); Zhang et al. (2004 ▶). For other 3-nitro­phthalic derivatives, see: Deng et al. (2007 ▶); Guo (2004 ▶); Song et al. (2007 ▶); Xiong & Qi (2007 ▶).

Experimental

Crystal data

[Co2(C8H3NO6)2(C10n class="Species">H8N2)3(H2O)6]

M = 1112.74

Monoclinic,

a = 15.672 (3) Å

b = 9.4283 (19) Å

c = 16.063 (3) Å

β = 103.92 (3)°

V = 2303.8 (8) Å3

Z = 2

Mo Kα radiation

μ = 0.81 mm−1

T = 293 K

0.21 × 0.15 × 0.12 mm

Data collection

Siemens SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.765, T max = 0.872

21789 measured reflections

5252 independent reflections

3669 reflections with I > 2σ(I)

R int = 0.079

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.134

S = 1.01

5252 reflections

352 parameters

9 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.38 e Å−3

Δρmin = −0.45 e Å−3

Data collection: SMART (Siemens, 1994 ▶); cell refinement: SAINT (Siemens, 1994 ▶); data reduction: SAIn class="Chemical">NT; 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/S160053680902875X/ya2101sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680902875X/ya2101Isup2.hkl

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

[Co2(C8H3NO6)2(C10H8N2)3(H2O)6]	F(000) = 1144
Mr = 1112.74	Dx = 1.604 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 21789 reflections
a = 15.672 (3) Å	θ = 3.0–27.5°
b = 9.4283 (19) Å	µ = 0.81 mm−1
c = 16.063 (3) Å	T = 293 K
β = 103.92 (3)°	Prism, pink
V = 2303.8 (8) Å3	0.21 × 0.15 × 0.12 mm
Z = 2

Siemens SMART CCD area-detector diffractometer	5252 independent reflections
Radiation source: fine-focus sealed tube	3669 reflections with I > 2σ(I)
graphite	Rint = 0.079
Detector resolution: no pixels mm-1	θmax = 27.5°, θmin = 3.0°
ω scans	h = −20→20
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −12→12
Tmin = 0.765, Tmax = 0.872	l = −20→19
21789 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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.134	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.075P)2] where P = (Fo2 + 2Fc2)/3
5252 reflections	(Δ/σ)max = 0.001
352 parameters	Δρmax = 0.38 e Å−3
9 restraints	Δρmin = −0.45 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	0.32172 (2)	0.70261 (4)	0.20771 (2)	0.02477 (14)
N1	0.17512 (19)	0.4939 (3)	−0.07320 (18)	0.0434 (7)
N2	0.24471 (16)	0.8547 (3)	0.12309 (15)	0.0299 (6)
N3	−0.0484 (2)	1.2759 (4)	−0.1856 (2)	0.0507 (8)
N4	0.35953 (16)	0.8342 (3)	0.31977 (14)	0.0288 (6)
O1	0.30328 (14)	0.5593 (2)	0.10689 (12)	0.0303 (5)
O2	0.22712 (15)	0.3866 (2)	0.15197 (13)	0.0398 (6)
O3	0.41953 (15)	0.2894 (2)	0.18540 (13)	0.0378 (6)
O4	0.43538 (15)	0.0753 (2)	0.13428 (14)	0.0395 (6)
O5	0.13514 (18)	0.5266 (3)	−0.02137 (16)	0.0565 (7)
O6	0.1662 (2)	0.5543 (4)	−0.14226 (19)	0.0909 (12)
O7	0.43623 (14)	0.7886 (2)	0.17266 (13)	0.0308 (5)
H7A	0.4781 (16)	0.782 (3)	0.2166 (14)	0.037*
H7B	0.4312 (19)	0.8724 (16)	0.1535 (17)	0.037*
O8	0.21785 (14)	0.6093 (3)	0.25287 (13)	0.0337 (5)
H8A	0.2092 (19)	0.534 (2)	0.2224 (18)	0.040*
H8B	0.1712 (13)	0.658 (3)	0.243 (2)	0.040*
O9	0.40189 (14)	0.5401 (2)	0.27330 (13)	0.0331 (5)
H9B	0.4550 (9)	0.560 (3)	0.2970 (18)	0.040*
H9C	0.4003 (18)	0.469 (2)	0.2406 (17)	0.040*
C1	0.28309 (19)	0.3469 (3)	0.02915 (18)	0.0272 (6)
C2	0.23784 (19)	0.3751 (3)	−0.05515 (18)	0.0312 (7)
C3	0.2485 (2)	0.2972 (4)	−0.1248 (2)	0.0386 (8)
H3A	0.2170	0.3202	−0.1800	0.046*
C4	0.3062 (2)	0.1854 (4)	−0.1112 (2)	0.0420 (8)
H4A	0.3132	0.1298	−0.1570	0.050*
C5	0.3537 (2)	0.1565 (3)	−0.02903 (19)	0.0359 (7)
H5A	0.3936	0.0817	−0.0203	0.043*
C6	0.34391 (19)	0.2355 (3)	0.04132 (18)	0.0283 (7)
C7	0.26975 (19)	0.4381 (3)	0.10318 (17)	0.0273 (6)
C8	0.4034 (2)	0.1983 (3)	0.12786 (19)	0.0290 (6)
C9	0.2360 (2)	0.8381 (4)	0.03926 (19)	0.0380 (8)
H9A	0.2676	0.7659	0.0210	0.046*
C10	0.1829 (2)	0.9217 (4)	−0.02198 (19)	0.0378 (8)
H10A	0.1795	0.9052	−0.0798	0.045*
C11	0.1994 (2)	0.9611 (4)	0.1467 (2)	0.0401 (8)
H11A	0.2049	0.9761	0.2050	0.048*
C12	0.1452 (2)	1.0492 (4)	0.0896 (2)	0.0400 (8)
H12A	0.1155	1.1221	0.1096	0.048*
C13	0.0546 (2)	1.0864 (4)	−0.1498 (2)	0.0481 (9)
H13A	0.0827	1.0105	−0.1690	0.058*
C14	−0.0048 (3)	1.1679 (5)	−0.2077 (2)	0.0558 (11)
H14A	−0.0148	1.1454	−0.2656	0.067*
C15	0.0285 (2)	1.2325 (4)	−0.0402 (2)	0.0442 (9)
H15A	0.0388	1.2599	0.0170	0.053*
C16	−0.0308 (3)	1.3064 (4)	−0.1027 (3)	0.0531 (10)
H16A	−0.0603	1.3824	−0.0855	0.064*
C17	0.13452 (19)	1.0300 (3)	0.00195 (19)	0.0300 (7)
C18	0.07229 (19)	1.1180 (4)	−0.06323 (19)	0.0320 (7)
C19	0.3917 (2)	0.9648 (3)	0.31517 (18)	0.0331 (7)
H19A	0.3766	1.0121	0.2629	0.040*
C20	0.4460 (2)	1.0327 (3)	0.38372 (18)	0.0310 (7)
H20A	0.4674	1.1229	0.3769	0.037*
C21	0.46875 (18)	0.9661 (3)	0.46269 (17)	0.0261 (6)
C22	0.4311 (2)	0.8345 (3)	0.46904 (18)	0.0336 (7)
H22A	0.4417	0.7880	0.5216	0.040*
C23	0.3779 (2)	0.7729 (4)	0.39713 (18)	0.0340 (7)
H23A	0.3536	0.6845	0.4027	0.041*

	U11	U22	U33	U12	U13	U23
Co1	0.0295 (2)	0.0217 (2)	0.0215 (2)	−0.00056 (17)	0.00289 (16)	−0.00077 (15)
N1	0.0390 (16)	0.0472 (19)	0.0376 (15)	0.0047 (14)	−0.0032 (14)	0.0032 (14)
N2	0.0317 (13)	0.0290 (15)	0.0277 (12)	0.0015 (11)	0.0045 (11)	0.0015 (11)
N3	0.0410 (17)	0.055 (2)	0.0513 (18)	0.0092 (15)	0.0009 (15)	0.0066 (15)
N4	0.0353 (14)	0.0283 (15)	0.0223 (11)	−0.0019 (11)	0.0062 (11)	−0.0032 (10)
O1	0.0412 (12)	0.0224 (12)	0.0254 (10)	−0.0036 (9)	0.0044 (9)	−0.0011 (8)
O2	0.0486 (14)	0.0332 (14)	0.0409 (12)	−0.0088 (11)	0.0170 (11)	−0.0025 (10)
O3	0.0447 (13)	0.0299 (13)	0.0323 (11)	0.0056 (10)	−0.0036 (10)	−0.0036 (9)
O4	0.0456 (13)	0.0205 (12)	0.0458 (13)	0.0039 (10)	−0.0020 (10)	0.0026 (9)
O5	0.0578 (16)	0.0590 (19)	0.0494 (15)	0.0215 (14)	0.0065 (13)	−0.0057 (13)
O6	0.103 (3)	0.112 (3)	0.0584 (18)	0.053 (2)	0.0208 (17)	0.0473 (19)
O7	0.0360 (12)	0.0228 (12)	0.0312 (11)	−0.0017 (9)	0.0032 (9)	0.0009 (9)
O8	0.0325 (11)	0.0340 (13)	0.0335 (11)	0.0033 (10)	0.0060 (10)	0.0027 (9)
O9	0.0364 (12)	0.0256 (12)	0.0321 (11)	0.0023 (9)	−0.0017 (10)	−0.0028 (9)
C1	0.0291 (15)	0.0228 (16)	0.0275 (14)	−0.0066 (12)	0.0026 (12)	−0.0011 (12)
C2	0.0311 (16)	0.0282 (18)	0.0309 (15)	−0.0014 (13)	0.0008 (13)	0.0008 (13)
C3	0.0413 (18)	0.045 (2)	0.0258 (15)	−0.0057 (16)	0.0006 (14)	−0.0006 (14)
C4	0.051 (2)	0.045 (2)	0.0306 (16)	−0.0083 (17)	0.0111 (15)	−0.0097 (15)
C5	0.0416 (18)	0.0237 (17)	0.0419 (18)	−0.0010 (14)	0.0091 (15)	−0.0062 (14)
C6	0.0312 (16)	0.0218 (16)	0.0310 (15)	−0.0052 (12)	0.0054 (13)	0.0008 (12)
C7	0.0299 (15)	0.0229 (16)	0.0248 (14)	0.0017 (12)	−0.0020 (12)	−0.0007 (11)
C8	0.0307 (15)	0.0221 (16)	0.0320 (15)	−0.0039 (13)	0.0034 (13)	0.0023 (13)
C9	0.052 (2)	0.0327 (19)	0.0304 (16)	0.0115 (15)	0.0128 (15)	0.0041 (14)
C10	0.0468 (19)	0.041 (2)	0.0246 (15)	0.0107 (16)	0.0062 (14)	0.0040 (14)
C11	0.0445 (19)	0.042 (2)	0.0309 (16)	0.0059 (16)	0.0044 (15)	−0.0068 (15)
C12	0.0460 (19)	0.037 (2)	0.0340 (16)	0.0140 (16)	0.0048 (15)	−0.0081 (14)
C13	0.044 (2)	0.054 (2)	0.0421 (19)	0.0178 (17)	0.0011 (16)	−0.0041 (17)
C14	0.049 (2)	0.073 (3)	0.0392 (19)	0.020 (2)	−0.0007 (18)	−0.0034 (19)
C15	0.048 (2)	0.042 (2)	0.0410 (19)	0.0125 (17)	0.0076 (16)	0.0008 (16)
C16	0.056 (2)	0.042 (2)	0.060 (2)	0.0207 (18)	0.012 (2)	0.0046 (18)
C17	0.0271 (15)	0.0279 (17)	0.0345 (16)	0.0007 (13)	0.0062 (13)	0.0043 (13)
C18	0.0262 (15)	0.0337 (18)	0.0348 (16)	0.0024 (13)	0.0050 (13)	0.0026 (13)
C19	0.0444 (18)	0.0284 (18)	0.0246 (14)	−0.0008 (14)	0.0046 (13)	−0.0019 (12)
C20	0.0388 (17)	0.0259 (17)	0.0275 (14)	−0.0041 (13)	0.0061 (13)	−0.0022 (12)
C21	0.0292 (14)	0.0260 (16)	0.0232 (13)	−0.0017 (12)	0.0064 (12)	−0.0039 (12)
C22	0.0441 (18)	0.0344 (19)	0.0216 (14)	−0.0050 (14)	0.0065 (13)	0.0015 (13)
C23	0.0416 (18)	0.0325 (19)	0.0275 (15)	−0.0122 (14)	0.0077 (14)	−0.0028 (13)

Co1—O1	2.075 (2)	C4—C5	1.378 (4)
Co1—O9	2.097 (2)	C4—H4A	0.9300
Co1—O8	2.126 (2)	C5—C6	1.393 (4)
Co1—N2	2.138 (2)	C5—H5A	0.9300
Co1—N4	2.149 (2)	C6—C8	1.517 (4)
Co1—O7	2.164 (2)	C9—C10	1.374 (4)
N1—O5	1.197 (4)	C9—H9A	0.9300
N1—O6	1.225 (4)	C10—C17	1.380 (4)
N1—C2	1.472 (4)	C10—H10A	0.9300
N2—C9	1.330 (4)	C11—C12	1.370 (4)
N2—C11	1.336 (4)	C11—H11A	0.9300
N3—C14	1.322 (5)	C12—C17	1.388 (4)
N3—C16	1.325 (5)	C12—H12A	0.9300
N4—C23	1.337 (4)	C13—C14	1.380 (5)
N4—C19	1.339 (4)	C13—C18	1.384 (4)
O1—C7	1.253 (4)	C13—H13A	0.9300
O2—C7	1.244 (4)	C14—H14A	0.9300
O3—C8	1.242 (4)	C15—C18	1.376 (5)
O4—C8	1.257 (4)	C15—C16	1.382 (5)
O7—H7A	0.842 (10)	C15—H15A	0.9300
O7—H7B	0.845 (10)	C16—H16A	0.9300
O8—H8A	0.854 (10)	C17—C18	1.498 (4)
O8—H8B	0.847 (10)	C19—C20	1.377 (4)
O9—H9B	0.849 (10)	C19—H19A	0.9300
O9—H9C	0.849 (10)	C20—C21	1.383 (4)
C1—C2	1.395 (4)	C20—H20A	0.9300
C1—C6	1.401 (4)	C21—C22	1.388 (4)
C1—C7	1.522 (4)	C21—C21i	1.497 (5)
C2—C3	1.382 (4)	C22—C23	1.380 (4)
C3—C4	1.372 (5)	C22—H22A	0.9300
C3—H3A	0.9300	C23—H23A	0.9300
O1—Co1—O9	82.56 (8)	C1—C6—C8	123.3 (3)
O1—Co1—O8	91.30 (9)	O2—C7—O1	127.5 (3)
O9—Co1—O8	86.66 (9)	O2—C7—C1	117.9 (3)
O1—Co1—N2	89.37 (9)	O1—C7—C1	114.7 (3)
O9—Co1—N2	170.96 (9)	O3—C8—O4	124.8 (3)
O8—Co1—N2	97.64 (9)	O3—C8—C6	119.5 (3)
O1—Co1—N4	171.19 (9)	O4—C8—C6	115.7 (3)
O9—Co1—N4	89.42 (9)	N2—C9—C10	123.7 (3)
O8—Co1—N4	91.87 (9)	N2—C9—H9A	118.2
N2—Co1—N4	98.34 (10)	C10—C9—H9A	118.2
O1—Co1—O7	90.54 (8)	C9—C10—C17	120.3 (3)
O9—Co1—O7	88.29 (9)	C9—C10—H10A	119.9
O8—Co1—O7	174.37 (8)	C17—C10—H10A	119.9
N2—Co1—O7	87.70 (9)	N2—C11—C12	123.4 (3)
N4—Co1—O7	85.57 (9)	N2—C11—H11A	118.3
O5—N1—O6	123.1 (3)	C12—C11—H11A	118.3
O5—N1—C2	119.7 (3)	C11—C12—C17	120.3 (3)
O6—N1—C2	117.2 (3)	C11—C12—H12A	119.9
C9—N2—C11	116.3 (3)	C17—C12—H12A	119.9
C9—N2—Co1	118.0 (2)	C14—C13—C18	119.8 (3)
C11—N2—Co1	125.5 (2)	C14—C13—H13A	120.1
C14—N3—C16	116.1 (3)	C18—C13—H13A	120.1
C23—N4—C19	116.7 (3)	N3—C14—C13	123.8 (3)
C23—N4—Co1	118.9 (2)	N3—C14—H14A	118.1
C19—N4—Co1	121.1 (2)	C13—C14—H14A	118.1
C7—O1—Co1	127.50 (19)	C18—C15—C16	119.5 (3)
Co1—O7—H7A	106 (2)	C18—C15—H15A	120.3
Co1—O7—H7B	116 (2)	C16—C15—H15A	120.3
H7A—O7—H7B	110.9 (16)	N3—C16—C15	124.2 (4)
Co1—O8—H8A	100 (2)	N3—C16—H16A	117.9
Co1—O8—H8B	114 (2)	C15—C16—H16A	117.9
H8A—O8—H8B	109.6 (16)	C10—C17—C12	116.0 (3)
Co1—O9—H9B	118 (2)	C10—C17—C18	121.6 (3)
Co1—O9—H9C	110 (2)	C12—C17—C18	122.4 (3)
H9B—O9—H9C	109.4 (16)	C15—C18—C13	116.5 (3)
C2—C1—C6	116.7 (3)	C15—C18—C17	121.9 (3)
C2—C1—C7	121.2 (3)	C13—C18—C17	121.5 (3)
C6—C1—C7	122.1 (2)	N4—C19—C20	123.5 (3)
C3—C2—C1	123.5 (3)	N4—C19—H19A	118.2
C3—C2—N1	116.7 (3)	C20—C19—H19A	118.2
C1—C2—N1	119.7 (3)	C19—C20—C21	119.7 (3)
C4—C3—C2	118.9 (3)	C19—C20—H20A	120.1
C4—C3—H3A	120.6	C21—C20—H20A	120.1
C2—C3—H3A	120.6	C20—C21—C22	116.9 (3)
C3—C4—C5	119.2 (3)	C20—C21—C21i	121.0 (3)
C3—C4—H4A	120.4	C22—C21—C21i	122.0 (3)
C5—C4—H4A	120.4	C23—C22—C21	119.8 (3)
C4—C5—C6	122.1 (3)	C23—C22—H22A	120.1
C4—C5—H5A	118.9	C21—C22—H22A	120.1
C6—C5—H5A	118.9	N4—C23—C22	123.2 (3)
C5—C6—C1	119.5 (3)	N4—C23—H23A	118.4
C5—C6—C8	117.2 (3)	C22—C23—H23A	118.4
O1—Co1—N2—C9	−21.2 (2)	C2—C1—C7—O2	106.9 (3)
O8—Co1—N2—C9	−112.4 (2)	C6—C1—C7—O2	−76.2 (4)
N4—Co1—N2—C9	154.5 (2)	C2—C1—C7—O1	−72.5 (4)
O7—Co1—N2—C9	69.3 (2)	C6—C1—C7—O1	104.5 (3)
O1—Co1—N2—C11	154.2 (3)	C5—C6—C8—O3	155.8 (3)
O8—Co1—N2—C11	63.0 (3)	C1—C6—C8—O3	−21.8 (5)
N4—Co1—N2—C11	−30.1 (3)	C5—C6—C8—O4	−21.9 (4)
O7—Co1—N2—C11	−115.2 (3)	C1—C6—C8—O4	160.4 (3)
O9—Co1—N4—C23	−31.5 (2)	C11—N2—C9—C10	−1.1 (5)
O8—Co1—N4—C23	55.1 (2)	Co1—N2—C9—C10	174.7 (3)
N2—Co1—N4—C23	153.1 (2)	N2—C9—C10—C17	−0.1 (5)
O7—Co1—N4—C23	−119.9 (2)	C9—N2—C11—C12	0.9 (5)
O9—Co1—N4—C19	127.1 (2)	Co1—N2—C11—C12	−174.5 (3)
O8—Co1—N4—C19	−146.3 (2)	N2—C11—C12—C17	0.5 (6)
N2—Co1—N4—C19	−48.3 (3)	C16—N3—C14—C13	1.5 (7)
O7—Co1—N4—C19	38.7 (2)	C18—C13—C14—N3	−1.1 (7)
O9—Co1—O1—C7	62.0 (2)	C14—N3—C16—C15	−0.5 (6)
O8—Co1—O1—C7	−24.5 (2)	C18—C15—C16—N3	−1.0 (6)
N2—Co1—O1—C7	−122.1 (2)	C9—C10—C17—C12	1.5 (5)
O7—Co1—O1—C7	150.2 (2)	C9—C10—C17—C18	−176.6 (3)
C6—C1—C2—C3	1.9 (5)	C11—C12—C17—C10	−1.7 (5)
C7—C1—C2—C3	179.0 (3)	C11—C12—C17—C18	176.5 (3)
C6—C1—C2—N1	−177.9 (3)	C16—C15—C18—C13	1.4 (5)
C7—C1—C2—N1	−0.8 (4)	C16—C15—C18—C17	−177.4 (3)
O5—N1—C2—C3	148.7 (3)	C14—C13—C18—C15	−0.5 (6)
O6—N1—C2—C3	−30.8 (5)	C14—C13—C18—C17	178.4 (4)
O5—N1—C2—C1	−31.5 (5)	C10—C17—C18—C15	−175.3 (3)
O6—N1—C2—C1	149.0 (3)	C12—C17—C18—C15	6.7 (5)
C1—C2—C3—C4	0.2 (5)	C10—C17—C18—C13	5.9 (5)
N1—C2—C3—C4	−180.0 (3)	C12—C17—C18—C13	−172.1 (3)
C2—C3—C4—C5	−1.8 (5)	C23—N4—C19—C20	4.3 (5)
C3—C4—C5—C6	1.3 (5)	Co1—N4—C19—C20	−154.8 (3)
C4—C5—C6—C1	0.9 (5)	N4—C19—C20—C21	−1.0 (5)
C4—C5—C6—C8	−176.8 (3)	C19—C20—C21—C22	−3.0 (5)
C2—C1—C6—C5	−2.4 (4)	C19—C20—C21—C21i	176.9 (3)
C7—C1—C6—C5	−179.5 (3)	C20—C21—C22—C23	3.6 (5)
C2—C1—C6—C8	175.2 (3)	C21i—C21—C22—C23	−176.3 (3)
C7—C1—C6—C8	−1.9 (5)	C19—N4—C23—C22	−3.6 (5)
Co1—O1—C7—O2	13.2 (4)	Co1—N4—C23—C22	156.0 (3)
Co1—O1—C7—C1	−167.53 (18)	C21—C22—C23—N4	−0.3 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7A···O3ii	0.84 (1)	1.96 (1)	2.798 (3)	173 (3)
O7—H7B···O4iii	0.85 (1)	1.94 (1)	2.772 (3)	167 (3)
O8—H8A···O2	0.85 (1)	1.86 (1)	2.677 (3)	161 (3)
O8—H8B···N3iv	0.85 (1)	2.02 (2)	2.830 (4)	159 (3)
O9—H9B···O4ii	0.85 (1)	1.81 (1)	2.645 (3)	167 (3)
O9—H9C···O3	0.85 (1)	1.97 (1)	2.801 (3)	167 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O7—H7A⋯O3i	0.842 (10)	1.960 (11)	2.798 (3)	173 (3)
O7—H7B⋯O4ii	0.845 (10)	1.942 (12)	2.772 (3)	167 (3)
O8—H8A⋯O2	0.854 (10)	1.855 (13)	2.677 (3)	161 (3)
O8—H8B⋯N3iii	0.847 (10)	2.021 (15)	2.830 (4)	159 (3)
O9—H9B⋯O4i	0.849 (10)	1.810 (13)	2.645 (3)	167 (3)
O9—H9C⋯O3	0.849 (10)	1.968 (13)	2.801 (3)	167 (3)

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