Poly[[tetra-aqua-tetra-kis-[μ(3)-5-(pyridine-4-carboxamido)-isophthalato]-cobalt(II)-diholmium(III)] tetra-hydrate].

In the centrosymmetric polymeric title compound, {[CoHo(2)(C(14)H(8)N(2)O(5))(4)(H(2)O)(4)]·4H(2)O}(n), the Ho(III) ion is coordinated by one water mol-ecule and four 5-(pyridine-4-carboxamido)-isophthalate (L) ligands in a distorted square-anti-prismatic arrangement. The Co(II) ion, located on an inversion center, is coordinated by two pyridine N atoms, two carboxyl-ate O atoms and two water mol-ecules in a distorted octa-hedral geometry. One L ligand bridges two Ho ions and one Co ion through two carboxyl-ate groups and one pyridine N atom. The other L ligand bridges two Ho ions and one Co ion through two carboxyl-ate groups, while the uncoordinated pyridine N atom accepts a hydrogen bond from an adjacent coordinated water mol-ecule. Extensive O-H⋯O, N-H⋯O and O-H⋯N hydrogen bonding is present in the crystal.

Related literature

For related hetero-metallic complexes, see: Chen et al. (2011 ▶); Deng et al. (2011 ▶); Gu & Xue (2006 ▶); Liang et al. (2000 ▶); Prasad et al. (2007 ▶); Zhao et al. (2003 ▶, 2004 ▶).

Experimental

Crystal data

[CoHo2(C14H8N2O5)4(H2O)4]·4H2O

M = 1669.81

Triclinic,

a = 10.0597 (9) Å

b = 10.7824 (10) Å

c = 13.7261 (13) Å

α = 79.141 (3)°

β = 78.801 (1)°

γ = 86.578 (3)°

V = 1433.9 (2) Å3

Z = 1

Mo Kα radiation

μ = 3.12 mm−1

T = 291 K

0.20 × 0.14 × 0.10 mm

Data collection

Bruker APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.574, T max = 0.746

7154 measured reflections

4968 independent reflections

4756 reflections with I > 2σ(I)

R int = 0.070

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.123

S = 1.06

4968 reflections

430 parameters

H-atom parameters constrained

Δρmax = 2.89 e Å−3

Δρmin = −1.93 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: XP in SHELXTL, and DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811042814/hy2478sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811042814/hy2478Isup2.hkl

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

[CoHo2(C14H8N2O5)4(H2O)4]·4H2O	Z = 1
Mr = 1669.81	F(000) = 825
Triclinic, P1	Dx = 1.934 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.0597 (9) Å	Cell parameters from 5442 reflections
b = 10.7824 (10) Å	θ = 2.7–28.1°
c = 13.7261 (13) Å	µ = 3.12 mm−1
α = 79.141 (3)°	T = 291 K
β = 78.801 (1)°	Block, pink
γ = 86.578 (3)°	0.20 × 0.14 × 0.10 mm
V = 1433.9 (2) Å3

Bruker APEX CCD diffractometer	4968 independent reflections
Radiation source: fine-focus sealed tube	4756 reflections with I > 2σ(I)
graphite	Rint = 0.070
φ and ω scans	θmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −11→11
Tmin = 0.574, Tmax = 0.746	k = −12→10
7154 measured reflections	l = −15→16

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0881P)2] where P = (Fo2 + 2Fc2)/3
4968 reflections	(Δ/σ)max = 0.002
430 parameters	Δρmax = 2.89 e Å−3
0 restraints	Δρmin = −1.93 e Å−3

	x	y	z	Uiso*/Ueq
Co1	1.0000	0.5000	0.0000	0.0253 (3)
Ho1	0.68057 (2)	1.07784 (2)	0.204341 (17)	0.01470 (13)
C1	0.6994 (6)	0.4719 (5)	0.2279 (4)	0.0217 (12)
C2	0.7035 (6)	0.6032 (6)	0.1993 (5)	0.0236 (13)
H2	0.7193	0.6407	0.1315	0.028*
C3	0.6834 (6)	0.6770 (5)	0.2746 (4)	0.0221 (12)
C4	0.6647 (6)	0.6223 (6)	0.3756 (5)	0.0229 (12)
H4	0.6529	0.6730	0.4246	0.027*
C5	0.6636 (6)	0.4913 (6)	0.4041 (5)	0.0233 (12)
C6	0.6770 (6)	0.4169 (6)	0.3298 (5)	0.0240 (13)
H6	0.6709	0.3296	0.3485	0.029*
C7	0.6875 (6)	0.8177 (6)	0.2476 (5)	0.0236 (13)
C8	0.7308 (6)	0.3913 (6)	0.1481 (5)	0.0228 (13)
C9	0.6680 (7)	0.4839 (6)	0.5835 (5)	0.0289 (14)
C10	0.6509 (6)	0.4012 (6)	0.6856 (5)	0.0264 (13)
C11	0.6448 (8)	0.4618 (7)	0.7689 (5)	0.0363 (16)
H11	0.6452	0.5494	0.7600	0.044*
C12	0.6382 (8)	0.3898 (8)	0.8632 (6)	0.0425 (18)
H12	0.6334	0.4310	0.9176	0.051*
C13	0.6446 (7)	0.2083 (7)	0.8032 (5)	0.0366 (16)
H13	0.6453	0.1205	0.8150	0.044*
C14	0.6503 (7)	0.2708 (7)	0.7046 (5)	0.0325 (15)
H14	0.6536	0.2260	0.6525	0.039*
C15	0.9066 (6)	1.1082 (6)	0.2811 (5)	0.0229 (13)
C16	1.0260 (6)	1.1190 (6)	0.3296 (5)	0.0238 (13)
C17	1.1593 (6)	1.1035 (6)	0.2809 (5)	0.0248 (13)
H17	1.1774	1.0870	0.2154	0.030*
C18	1.2633 (6)	1.1125 (6)	0.3300 (5)	0.0228 (13)
C19	1.2362 (6)	1.1400 (6)	0.4285 (5)	0.0252 (13)
H19	1.3070	1.1440	0.4623	0.030*
C20	1.1051 (6)	1.1606 (6)	0.4744 (4)	0.0231 (12)
C21	0.9979 (6)	1.1474 (6)	0.4250 (5)	0.0234 (13)
H21	0.9086	1.1579	0.4568	0.028*
C22	1.4092 (6)	1.0971 (5)	0.2832 (5)	0.0229 (13)
C23	0.9939 (6)	1.2942 (6)	0.5906 (5)	0.0257 (13)
C24	0.9915 (6)	1.3357 (6)	0.6897 (5)	0.0264 (13)
C25	0.9898 (7)	1.4651 (7)	0.6893 (5)	0.0302 (15)
H25	0.9920	1.5228	0.6294	0.036*
C26	0.9847 (7)	1.5063 (6)	0.7794 (5)	0.0294 (14)
H26	0.9852	1.5929	0.7780	0.035*
C27	0.9748 (7)	1.3039 (6)	0.8680 (5)	0.0313 (15)
H27	0.9658	1.2485	0.9295	0.038*
C28	0.9831 (7)	1.2549 (6)	0.7813 (5)	0.0306 (14)
H28	0.9831	1.1679	0.7844	0.037*
N1	0.6462 (5)	0.4309 (5)	0.5055 (4)	0.0259 (11)
H1	0.6196	0.3541	0.5196	0.031*
N2	0.6383 (6)	0.2642 (6)	0.8813 (5)	0.0399 (14)
N3	1.0799 (5)	1.1948 (5)	0.5708 (4)	0.0260 (11)
H3	1.1190	1.1529	0.6176	0.031*
N4	0.9792 (5)	1.4296 (5)	0.8675 (4)	0.0269 (12)
O1	0.8061 (5)	0.4321 (4)	0.0666 (3)	0.0333 (11)
O2	0.6754 (5)	0.2834 (4)	0.1695 (4)	0.0331 (11)
O3	0.7064 (6)	0.8823 (4)	0.3105 (4)	0.0398 (13)
O4	0.6712 (6)	0.8746 (4)	0.1615 (4)	0.0411 (13)
O5	0.6942 (7)	0.5942 (5)	0.5749 (4)	0.0603 (18)
O6	0.7902 (4)	1.1165 (4)	0.3309 (3)	0.0270 (9)
O7	0.9238 (5)	1.0921 (5)	0.1893 (3)	0.0320 (11)
O8	1.4436 (5)	1.0967 (5)	0.1889 (4)	0.0333 (11)
O9	1.4993 (5)	1.0839 (5)	0.3355 (3)	0.0405 (12)
O10	0.9226 (5)	1.3484 (5)	0.5328 (4)	0.0421 (13)
O1W	0.9246 (5)	0.6839 (4)	−0.0658 (3)	0.0366 (11)
H1WA	0.8426	0.7036	−0.0440	0.044*
H1WB	0.9828	0.7414	−0.0764	0.044*
O2W	0.7208 (5)	1.0991 (5)	0.0330 (3)	0.0399 (12)
H2WA	0.8039	1.0888	0.0078	0.048*
H2WB	0.6856	1.1678	0.0062	0.048*
O3W	0.5839 (8)	0.1598 (5)	0.5164 (4)	0.0640 (19)
H3WA	0.6415	0.1444	0.4657	0.077*
H3WB	0.5633	0.0901	0.5562	0.077*
O4W	0.3038 (7)	0.1634 (8)	0.0325 (5)	0.084 (3)
H4WA	0.3255	0.1440	−0.0260	0.101*
H4WB	0.3604	0.1340	0.0701	0.101*

	U11	U22	U33	U12	U13	U23
Co1	0.0279 (7)	0.0260 (6)	0.0239 (6)	−0.0029 (5)	−0.0040 (5)	−0.0097 (5)
Ho1	0.01438 (18)	0.01247 (18)	0.01903 (18)	0.00036 (11)	−0.00550 (11)	−0.00507 (11)
C1	0.021 (3)	0.019 (3)	0.027 (3)	0.002 (2)	−0.008 (2)	−0.008 (2)
C2	0.019 (3)	0.022 (3)	0.028 (3)	−0.001 (2)	−0.001 (2)	−0.002 (2)
C3	0.025 (3)	0.018 (3)	0.026 (3)	0.001 (2)	−0.008 (2)	−0.007 (2)
C4	0.020 (3)	0.021 (3)	0.029 (3)	0.002 (2)	−0.006 (2)	−0.006 (2)
C5	0.015 (3)	0.024 (3)	0.029 (3)	0.003 (2)	−0.002 (2)	−0.005 (2)
C6	0.027 (3)	0.018 (3)	0.026 (3)	0.000 (2)	−0.003 (3)	−0.006 (2)
C7	0.024 (3)	0.023 (3)	0.024 (3)	0.006 (2)	−0.007 (2)	−0.002 (3)
C8	0.017 (3)	0.024 (3)	0.029 (3)	0.000 (2)	−0.008 (2)	−0.005 (3)
C9	0.036 (4)	0.026 (3)	0.029 (3)	−0.005 (3)	−0.013 (3)	−0.005 (3)
C10	0.022 (3)	0.028 (3)	0.030 (3)	0.004 (2)	−0.010 (3)	−0.003 (3)
C11	0.044 (4)	0.036 (4)	0.032 (4)	0.003 (3)	−0.008 (3)	−0.011 (3)
C12	0.046 (5)	0.055 (5)	0.030 (4)	0.000 (4)	−0.008 (3)	−0.016 (4)
C13	0.037 (4)	0.037 (4)	0.037 (4)	−0.007 (3)	−0.017 (3)	0.000 (3)
C14	0.032 (4)	0.039 (4)	0.029 (3)	−0.007 (3)	−0.011 (3)	−0.005 (3)
C15	0.018 (3)	0.022 (3)	0.031 (3)	−0.003 (2)	−0.005 (3)	−0.010 (3)
C16	0.020 (3)	0.023 (3)	0.031 (3)	0.000 (2)	−0.008 (3)	−0.008 (3)
C17	0.023 (3)	0.027 (3)	0.025 (3)	0.002 (2)	−0.005 (2)	−0.005 (2)
C18	0.020 (3)	0.022 (3)	0.028 (3)	−0.001 (2)	−0.005 (2)	−0.007 (2)
C19	0.019 (3)	0.030 (3)	0.030 (3)	0.002 (2)	−0.013 (3)	−0.007 (3)
C20	0.023 (3)	0.024 (3)	0.026 (3)	0.005 (2)	−0.010 (2)	−0.011 (2)
C21	0.016 (3)	0.029 (3)	0.028 (3)	−0.001 (2)	−0.006 (2)	−0.010 (3)
C22	0.021 (3)	0.019 (3)	0.028 (3)	0.000 (2)	−0.003 (3)	−0.003 (2)
C23	0.019 (3)	0.034 (3)	0.026 (3)	0.001 (3)	−0.006 (3)	−0.011 (3)
C24	0.018 (3)	0.039 (4)	0.026 (3)	0.003 (3)	−0.007 (2)	−0.015 (3)
C25	0.029 (4)	0.038 (4)	0.025 (3)	0.000 (3)	−0.008 (3)	−0.008 (3)
C26	0.030 (4)	0.029 (3)	0.031 (3)	−0.001 (3)	−0.004 (3)	−0.013 (3)
C27	0.033 (4)	0.030 (4)	0.032 (4)	−0.005 (3)	−0.008 (3)	−0.004 (3)
C28	0.032 (4)	0.030 (3)	0.032 (3)	−0.006 (3)	−0.005 (3)	−0.014 (3)
N1	0.034 (3)	0.018 (3)	0.025 (3)	0.001 (2)	−0.006 (2)	0.001 (2)
N2	0.041 (4)	0.046 (4)	0.033 (3)	−0.002 (3)	−0.011 (3)	−0.002 (3)
N3	0.023 (3)	0.030 (3)	0.026 (3)	0.000 (2)	−0.004 (2)	−0.010 (2)
N4	0.024 (3)	0.032 (3)	0.028 (3)	−0.004 (2)	−0.005 (2)	−0.014 (2)
O1	0.033 (3)	0.039 (3)	0.029 (2)	−0.011 (2)	0.001 (2)	−0.011 (2)
O2	0.044 (3)	0.021 (2)	0.038 (3)	−0.004 (2)	−0.010 (2)	−0.009 (2)
O3	0.073 (4)	0.019 (2)	0.036 (3)	0.003 (2)	−0.031 (3)	−0.008 (2)
O4	0.074 (4)	0.021 (2)	0.032 (3)	0.001 (2)	−0.021 (3)	−0.003 (2)
O5	0.113 (6)	0.034 (3)	0.040 (3)	−0.025 (3)	−0.026 (3)	−0.001 (2)
O6	0.018 (2)	0.035 (2)	0.033 (2)	−0.0004 (18)	−0.0057 (18)	−0.0164 (19)
O7	0.026 (2)	0.048 (3)	0.027 (2)	−0.002 (2)	−0.0062 (19)	−0.020 (2)
O8	0.022 (2)	0.049 (3)	0.033 (3)	0.003 (2)	−0.007 (2)	−0.019 (2)
O9	0.018 (2)	0.074 (4)	0.032 (3)	0.006 (2)	−0.009 (2)	−0.013 (2)
O10	0.040 (3)	0.054 (3)	0.043 (3)	0.019 (2)	−0.022 (2)	−0.027 (2)
O1W	0.038 (3)	0.034 (3)	0.036 (3)	0.005 (2)	−0.005 (2)	−0.004 (2)
O2W	0.053 (3)	0.034 (3)	0.031 (3)	0.002 (2)	−0.008 (2)	−0.001 (2)
O3W	0.120 (6)	0.037 (3)	0.035 (3)	−0.023 (3)	−0.009 (3)	−0.008 (2)
O4W	0.059 (4)	0.155 (8)	0.039 (3)	0.029 (4)	−0.018 (3)	−0.022 (4)

Co1—O1	2.098 (4)	C13—H13	0.9300
Co1—O1i	2.098 (4)	C14—H14	0.9300
Co1—N4ii	2.148 (5)	C15—O6	1.243 (7)
Co1—N4iii	2.148 (5)	C15—O7	1.282 (7)
Co1—O1Wi	2.176 (5)	C15—C16	1.502 (8)
Co1—O1W	2.176 (5)	C16—C21	1.373 (8)
Ho1—O2iv	2.177 (4)	C16—C17	1.393 (9)
Ho1—O2W	2.278 (5)	C17—C18	1.367 (9)
Ho1—O9v	2.307 (5)	C17—H17	0.9300
Ho1—O6	2.341 (4)	C18—C19	1.411 (8)
Ho1—O3	2.358 (4)	C18—C22	1.496 (8)
Ho1—O4	2.385 (4)	C19—C20	1.371 (9)
Ho1—O8v	2.427 (5)	C19—H19	0.9300
Ho1—O7	2.426 (5)	C20—C21	1.408 (8)
Ho1—C22v	2.745 (6)	C20—N3	1.412 (7)
C1—C6	1.393 (8)	C21—H21	0.9300
C1—C2	1.397 (8)	C22—O9	1.248 (7)
C1—C8	1.499 (8)	C22—O8	1.274 (8)
C2—C3	1.397 (8)	C23—O10	1.217 (8)
C2—H2	0.9300	C23—N3	1.370 (8)
C3—C4	1.381 (9)	C23—C24	1.506 (8)
C3—C7	1.494 (8)	C24—C28	1.379 (9)
C4—C5	1.393 (8)	C24—C25	1.394 (10)
C4—H4	0.9300	C25—C26	1.382 (9)
C5—C6	1.394 (8)	C25—H25	0.9300
C5—N1	1.403 (8)	C26—N4	1.324 (9)
C6—H6	0.9300	C26—H26	0.9300
C7—O3	1.254 (8)	C27—N4	1.358 (9)
C7—O4	1.261 (8)	C27—C28	1.377 (9)
C8—O1	1.242 (7)	C27—H27	0.9300
C8—O2	1.279 (7)	C28—H28	0.9300
C9—O5	1.212 (8)	N1—H1	0.8600
C9—N1	1.363 (8)	N3—H3	0.8600
C9—C10	1.498 (9)	O1W—H1WA	0.8500
C10—C14	1.382 (10)	O1W—H1WB	0.8510
C10—C11	1.409 (9)	O2W—H2WA	0.8500
C11—C12	1.370 (10)	O2W—H2WB	0.8520
C11—H11	0.9300	O3W—H3WA	0.8503
C12—N2	1.331 (10)	O3W—H3WB	0.8522
C12—H12	0.9300	O4W—H4WA	0.8514
C13—N2	1.315 (9)	O4W—H4WB	0.8504
C13—C14	1.385 (10)
O1—Co1—O1i	180.0 (2)	C12—C11—H11	120.4
O1—Co1—N4ii	92.16 (19)	C10—C11—H11	120.4
O1i—Co1—N4ii	87.84 (19)	N2—C12—C11	123.6 (7)
O1—Co1—N4iii	87.84 (19)	N2—C12—H12	118.2
O1i—Co1—N4iii	92.16 (19)	C11—C12—H12	118.2
N4ii—Co1—N4iii	180.0 (3)	N2—C13—C14	124.7 (7)
O1—Co1—O1Wi	85.97 (19)	N2—C13—H13	117.6
O1i—Co1—O1Wi	94.03 (19)	C14—C13—H13	117.6
N4ii—Co1—O1Wi	89.3 (2)	C10—C14—C13	118.4 (6)
N4iii—Co1—O1Wi	90.7 (2)	C10—C14—H14	120.8
O1—Co1—O1W	94.03 (19)	C13—C14—H14	120.8
O1i—Co1—O1W	85.97 (19)	O6—C15—O7	120.1 (5)
N4ii—Co1—O1W	90.7 (2)	O6—C15—C16	119.1 (5)
N4iii—Co1—O1W	89.3 (2)	O7—C15—C16	120.8 (5)
O1Wi—Co1—O1W	180.0 (2)	C21—C16—C17	120.8 (6)
O2iv—Ho1—O2W	82.48 (17)	C21—C16—C15	116.6 (5)
O2iv—Ho1—O9v	89.62 (19)	C17—C16—C15	122.6 (5)
O2W—Ho1—O9v	138.85 (17)	C18—C17—C16	119.6 (6)
O2iv—Ho1—O6	81.57 (16)	C18—C17—H17	120.2
O2W—Ho1—O6	138.55 (17)	C16—C17—H17	120.2
O9v—Ho1—O6	78.95 (15)	C17—C18—C19	120.3 (6)
O2iv—Ho1—O3	153.22 (17)	C17—C18—C22	123.0 (6)
O2W—Ho1—O3	122.18 (16)	C19—C18—C22	116.7 (5)
O9v—Ho1—O3	78.12 (19)	C20—C19—C18	119.9 (6)
O6—Ho1—O3	72.81 (15)	C20—C19—H19	120.1
O2iv—Ho1—O4	152.59 (18)	C18—C19—H19	120.1
O2W—Ho1—O4	71.43 (17)	C19—C20—C21	119.7 (5)
O9v—Ho1—O4	104.37 (19)	C19—C20—N3	119.3 (5)
O6—Ho1—O4	123.81 (16)	C21—C20—N3	121.0 (5)
O3—Ho1—O4	54.16 (15)	C16—C21—C20	119.6 (6)
O2iv—Ho1—O8v	84.81 (18)	C16—C21—H21	120.2
O2W—Ho1—O8v	84.52 (17)	C20—C21—H21	120.2
O9v—Ho1—O8v	54.48 (15)	O9—C22—O8	118.7 (6)
O6—Ho1—O8v	131.43 (15)	O9—C22—C18	120.9 (5)
O3—Ho1—O8v	106.24 (18)	O8—C22—C18	120.4 (5)
O4—Ho1—O8v	84.49 (17)	O9—C22—Ho1vi	56.6 (3)
O2iv—Ho1—O7	86.64 (18)	O8—C22—Ho1vi	62.1 (3)
O2W—Ho1—O7	86.51 (17)	C18—C22—Ho1vi	176.7 (4)
O9v—Ho1—O7	133.46 (15)	O10—C23—N3	123.5 (6)
O6—Ho1—O7	54.60 (14)	O10—C23—C24	120.2 (6)
O3—Ho1—O7	84.87 (18)	N3—C23—C24	116.3 (5)
O4—Ho1—O7	99.70 (18)	C28—C24—C25	118.0 (6)
O8v—Ho1—O7	168.33 (16)	C28—C24—C23	124.5 (6)
O2iv—Ho1—C22v	86.17 (18)	C25—C24—C23	117.5 (6)
O2W—Ho1—C22v	112.05 (19)	C26—C25—C24	118.8 (6)
O9v—Ho1—C22v	26.84 (16)	C26—C25—H25	120.6
O6—Ho1—C22v	104.75 (16)	C24—C25—H25	120.6
O3—Ho1—C22v	92.79 (19)	N4—C26—C25	123.8 (6)
O4—Ho1—C22v	95.75 (18)	N4—C26—H26	118.1
O8v—Ho1—C22v	27.66 (17)	C25—C26—H26	118.1
O7—Ho1—C22v	158.98 (17)	N4—C27—C28	122.8 (6)
C6—C1—C2	120.0 (5)	N4—C27—H27	118.6
C6—C1—C8	120.6 (5)	C28—C27—H27	118.6
C2—C1—C8	119.2 (5)	C27—C28—C24	119.5 (6)
C3—C2—C1	118.7 (6)	C27—C28—H28	120.3
C3—C2—H2	120.6	C24—C28—H28	120.3
C1—C2—H2	120.6	C9—N1—C5	125.3 (5)
C4—C3—C2	121.3 (6)	C9—N1—H1	117.4
C4—C3—C7	118.1 (5)	C5—N1—H1	117.4
C2—C3—C7	120.6 (5)	C13—N2—C12	116.9 (6)
C3—C4—C5	120.0 (6)	C23—N3—C20	120.8 (5)
C3—C4—H4	120.0	C23—N3—H3	119.6
C5—C4—H4	120.0	C20—N3—H3	119.6
C4—C5—C6	119.2 (6)	C26—N4—C27	117.0 (6)
C4—C5—N1	122.4 (5)	C26—N4—Co1vii	121.1 (4)
C6—C5—N1	118.4 (5)	C27—N4—Co1vii	121.5 (4)
C1—C6—C5	120.7 (6)	C8—O1—Co1	144.4 (4)
C1—C6—H6	119.6	C8—O2—Ho1viii	153.1 (4)
C5—C6—H6	119.6	C7—O3—Ho1	94.4 (4)
O3—C7—O4	118.3 (6)	C7—O4—Ho1	93.0 (4)
O3—C7—C3	120.6 (5)	C15—O6—Ho1	95.1 (3)
O4—C7—C3	121.0 (6)	C15—O7—Ho1	90.1 (4)
O1—C8—O2	124.3 (6)	C22—O8—Ho1vi	90.2 (4)
O1—C8—C1	119.4 (5)	C22—O9—Ho1vi	96.5 (4)
O2—C8—C1	116.3 (5)	Co1—O1W—H1WA	117.2
O5—C9—N1	123.5 (6)	Co1—O1W—H1WB	112.7
O5—C9—C10	119.3 (6)	H1WA—O1W—H1WB	117.3
N1—C9—C10	117.1 (5)	Ho1—O2W—H2WA	113.0
C14—C10—C11	117.2 (6)	Ho1—O2W—H2WB	110.9
C14—C10—C9	125.8 (6)	H2WA—O2W—H2WB	113.5
C11—C10—C9	116.9 (6)	H3WA—O3W—H3WB	108.4
C12—C11—C10	119.1 (7)	H4WA—O4W—H4WB	112.3
C6—C1—C2—C3	−0.6 (9)	C6—C5—N1—C9	161.2 (6)
C8—C1—C2—C3	−175.6 (5)	C14—C13—N2—C12	−0.4 (11)
C1—C2—C3—C4	2.4 (9)	C11—C12—N2—C13	−0.3 (12)
C1—C2—C3—C7	179.7 (6)	O10—C23—N3—C20	9.1 (10)
C2—C3—C4—C5	−1.0 (9)	C24—C23—N3—C20	−170.5 (5)
C7—C3—C4—C5	−178.4 (5)	C19—C20—N3—C23	132.3 (6)
C3—C4—C5—C6	−2.1 (9)	C21—C20—N3—C23	−47.7 (8)
C3—C4—C5—N1	179.5 (6)	C25—C26—N4—C27	−1.8 (10)
C2—C1—C6—C5	−2.5 (9)	C25—C26—N4—Co1vii	171.2 (5)
C8—C1—C6—C5	172.4 (5)	C28—C27—N4—C26	3.5 (10)
C4—C5—C6—C1	3.9 (9)	C28—C27—N4—Co1vii	−169.4 (5)
N1—C5—C6—C1	−177.7 (5)	O2—C8—O1—Co1	−122.1 (7)
C4—C3—C7—O3	16.9 (9)	C1—C8—O1—Co1	58.6 (10)
C2—C3—C7—O3	−160.6 (6)	N4ii—Co1—O1—C8	−28.2 (8)
C4—C3—C7—O4	−162.6 (6)	N4iii—Co1—O1—C8	151.8 (8)
C2—C3—C7—O4	20.0 (9)	O1Wi—Co1—O1—C8	60.9 (7)
C6—C1—C8—O1	−148.0 (6)	O1W—Co1—O1—C8	−119.1 (7)
C2—C1—C8—O1	26.9 (8)	O1—C8—O2—Ho1viii	69.4 (12)
C6—C1—C8—O2	32.6 (8)	C1—C8—O2—Ho1viii	−111.3 (9)
C2—C1—C8—O2	−152.5 (6)	O4—C7—O3—Ho1	3.2 (7)
O5—C9—C10—C14	−165.1 (7)	C3—C7—O3—Ho1	−176.3 (5)
N1—C9—C10—C14	18.0 (10)	O2iv—Ho1—O3—C7	−179.7 (4)
O5—C9—C10—C11	10.0 (10)	O2W—Ho1—O3—C7	−25.1 (5)
N1—C9—C10—C11	−166.8 (6)	O9v—Ho1—O3—C7	115.9 (4)
C14—C10—C11—C12	−0.2 (10)	O6—Ho1—O3—C7	−162.2 (4)
C9—C10—C11—C12	−175.8 (7)	O4—Ho1—O3—C7	−1.8 (4)
C10—C11—C12—N2	0.6 (12)	O8v—Ho1—O3—C7	68.7 (4)
C11—C10—C14—C13	−0.4 (10)	O7—Ho1—O3—C7	−107.7 (4)
C9—C10—C14—C13	174.7 (6)	C22v—Ho1—O3—C7	93.3 (4)
N2—C13—C14—C10	0.7 (11)	O3—C7—O4—Ho1	−3.1 (7)
O6—C15—C16—C21	−4.9 (9)	C3—C7—O4—Ho1	176.3 (5)
O7—C15—C16—C21	174.4 (6)	O2iv—Ho1—O4—C7	179.8 (4)
O6—C15—C16—C17	176.2 (6)	O2W—Ho1—O4—C7	161.2 (5)
O7—C15—C16—C17	−4.6 (9)	O9v—Ho1—O4—C7	−61.6 (4)
C21—C16—C17—C18	2.2 (9)	O6—Ho1—O4—C7	24.6 (5)
C15—C16—C17—C18	−179.0 (6)	O3—Ho1—O4—C7	1.8 (4)
C16—C17—C18—C19	−1.3 (9)	O8v—Ho1—O4—C7	−112.8 (4)
C16—C17—C18—C22	180.0 (6)	O7—Ho1—O4—C7	78.2 (4)
C17—C18—C19—C20	−1.6 (9)	C22v—Ho1—O4—C7	−87.5 (4)
C22—C18—C19—C20	177.2 (6)	O7—C15—O6—Ho1	4.0 (6)
C18—C19—C20—C21	3.5 (9)	C16—C15—O6—Ho1	−176.8 (5)
C18—C19—C20—N3	−176.5 (6)	O2iv—Ho1—O6—C15	−94.1 (4)
C17—C16—C21—C20	−0.2 (9)	O2W—Ho1—O6—C15	−25.7 (5)
C15—C16—C21—C20	−179.2 (5)	O9v—Ho1—O6—C15	174.6 (4)
C19—C20—C21—C16	−2.6 (9)	O3—Ho1—O6—C15	93.8 (4)
N3—C20—C21—C16	177.4 (6)	O4—Ho1—O6—C15	74.6 (4)
C17—C18—C22—O9	−167.3 (6)	O8v—Ho1—O6—C15	−169.5 (3)
C19—C18—C22—O9	13.9 (9)	O7—Ho1—O6—C15	−2.2 (3)
C17—C18—C22—O8	12.4 (9)	C22v—Ho1—O6—C15	−177.9 (4)
C19—C18—C22—O8	−166.4 (6)	O6—C15—O7—Ho1	−3.8 (6)
O10—C23—C24—C28	133.8 (7)	C16—C15—O7—Ho1	176.9 (5)
N3—C23—C24—C28	−46.7 (9)	O2iv—Ho1—O7—C15	84.2 (4)
O10—C23—C24—C25	−42.3 (9)	O2W—Ho1—O7—C15	166.9 (4)
N3—C23—C24—C25	137.2 (6)	O9v—Ho1—O7—C15	−2.1 (5)
C28—C24—C25—C26	2.3 (9)	O6—Ho1—O7—C15	2.2 (3)
C23—C24—C25—C26	178.6 (6)	O3—Ho1—O7—C15	−70.4 (4)
C24—C25—C26—N4	−1.1 (10)	O4—Ho1—O7—C15	−122.7 (4)
N4—C27—C28—C24	−2.4 (10)	O8v—Ho1—O7—C15	127.1 (7)
C25—C24—C28—C27	−0.6 (10)	C22v—Ho1—O7—C15	14.0 (7)
C23—C24—C28—C27	−176.7 (6)	O9—C22—O8—Ho1vi	−2.7 (6)
O5—C9—N1—C5	6.6 (11)	C18—C22—O8—Ho1vi	177.6 (5)
C10—C9—N1—C5	−176.7 (6)	O8—C22—O9—Ho1vi	2.9 (6)
C4—C5—N1—C9	−20.3 (9)	C18—C22—O9—Ho1vi	−177.4 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O4Wix	0.85	2.00	2.761 (8)	149
O1W—H1WB···O7x	0.85	2.26	2.988 (7)	144
O2W—H2WB···N2xi	0.85	1.96	2.699 (8)	145
O3W—H3WA···O6viii	0.85	2.20	3.048 (8)	177
O3W—H3WB···O9xii	0.85	2.20	3.054 (8)	177
O4W—H4WA···O4ix	0.85	1.90	2.732 (8)	164
O4W—H4WB···O8xiii	0.85	1.94	2.752 (8)	160
N1—H1···O3W	0.86	2.16	2.996 (7)	165
N3—H3···O3ii	0.86	2.16	2.933 (7)	150

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WA⋯O4Wi	0.85	2.00	2.761 (8)	149
O1W—H1WB⋯O7ii	0.85	2.26	2.988 (7)	144
O2W—H2WB⋯N2iii	0.85	1.96	2.699 (8)	145
O3W—H3WA⋯O6iv	0.85	2.20	3.048 (8)	177
O3W—H3WB⋯O9v	0.85	2.20	3.054 (8)	177
O4W—H4WA⋯O4i	0.85	1.90	2.732 (8)	164
O4W—H4WB⋯O8vi	0.85	1.94	2.752 (8)	160
N1—H1⋯O3W	0.86	2.16	2.996 (7)	165
N3—H3⋯O3vii	0.86	2.16	2.933 (7)	150

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