catena-Poly[[cobalt(II)-μ-[N,N′-1,3-bis­(imidazol-1-ylmeth­yl)benzene]-κ²N³:N^3′-μ-(5-carboxy­benzene-1,3-dicarboxyl­ato)-κ²O¹:O³] monohydrate]

The title Co^II coordination polymer, {[Co(C₉H₄O₆)(C₁₄H₁₄N₄)]·H₂O}_n, was obtained by reaction of Co(NO₃)₂·6H₂O, benzene-1,3,5-tricarboxylic acid (H₃BTC) and 1,3-bis­(imidazol-1-ylmeth­yl)benzene (L). Each Co^II cation is four-coordinated by an O₂N₂ donor set in a distorted tetra­hedral geometry. The Co^II centers are connected into a one-dimensional double-stranded chain by HBTC anions and L ligands. The chains are further connected through hydrogen-bonding inter­actions between the hydroxyl groups of adjacent HBTC anions and face-to-face π–π inter­actions between the benzene rings of adjacent L ligands [average face-to-face distance of 3.427 (3) Å], resulting in the formation of a three-dimensional supra­molecular structure.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.047
• wR factor = 0.136
• Data-to-parameter ratio = 16.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       1.05

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      1.053
            Tmax scaled      0.926 Tmin scaled      0.895
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT794_ALERT_5_G Check Predicted Bond Valency for Co1         (2)       1.72
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          3

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   5 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

---

S1. Comment

As part of an investigation of the transition metal application there is a need to prepare further examples of these compounds. In this paper, the structure of the title compound, (I), is described.

As shown in Fig. 1, the Co^II ions is coordinated by two oxygen atoms from two HBTC anions and two nitrogen atoms from two L ligands. Each Co^II cation has a distorted tetrahedral coordination geometry. As illustrated in Fig. 2, each L ligand in (I) coordinates to two Co^II cations, thus acting as a bridging bidentate ligand. The Co^II cations are bridged by HBTC anions and L ligands to form a double-stranded chain, with the interchain Co···Co distance of 9.072 (6) Å. The hydroxyl groups of adjacent HBTC anions are involved in hydrogen bonding interactions. There also exist face-to-face π-π interactions between the benzene rings of L ligands of adjacent double-stranded chains (with centroid-to-centriod distance of 3.905 (2) Å, and average face-to-face distances of 3.427 (3) Å). These noncovalent interactions connect the whole structure to a 3-D supramolecular framework (Fig. 3). The lattice water molecule connects with HBTC anion via hydrogen bond.

Related literature

For related crystal structures, see Liu et al. (2007) and Xie et al. (2007).

S2. Experimental

The ligand L was synthesized according to the literature (Liu et al., 2007). A mixture of Co(NO₃)₂.6H₂O (0.11 g, 0.4 mmol), H₃BTC (0.10 g, 0.45 mmol), L (0.10 g, 0.4 mmol) and water (7 ml) was stirred for 10 min in air. The mixture was sealed in a Teflon reactor (15 ml) and heated at 180 °C for 3 days. After the mixture had been cooled to room temperature at 10 °C.h^-1, purple crystals of (I) were obtained. Yield: 30%.

S3. Refinement

The C-bound and hydroxy H-atoms were geometrically positioned (C—H 0.93–0.97 Å, O—H 0.82 Å) and refined using a riding model, with U_iso = 1.2–1.5U_eq (C, O). Water H atoms were located in a difference Fourier map and refined as riding atoms with U_iso(H) = 1.5U_eq(O).

Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1990); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures

	Fig. 1. A view of the local coordination of the Co^II cation in (I) showing the atomic numbering [symmetry code: (i) x + 1/2, -y + 1/2, z + 1/2]. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. Schematic view of the double-stranded chain in (I).
	Fig. 3. The packing diagram of (I). The hydrogen bonding interactions are indicated by dotted lines. H atoms omitted for clarity.

catena-Poly[[cobalt(II)-µ-[N,N'-1,3-bis(imidazol-1-ylmethyl)benzene]- κ²N³:N^3'-µ-(5-carboxybenzene-1,3-dicarboxylato)-κ²O¹:O³] monohydrate]

Crystal data

[Co(C9H4O6)(C14H14N4)]·H2O	F(000) = 1076
Mr = 523.36	Dx = 1.610 Mg m^−3
Monoclinic, P21/n	Melting point: not measured K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71069 Å
a = 7.8535 (4) Å	Cell parameters from 3606 reflections
b = 16.5308 (7) Å	θ = 1.7–28.3°
c = 16.7344 (8) Å	µ = 0.85 mm^−1
β = 96.350 (1)°	T = 293 K
V = 2159.21 (18) Å^3	Block, purple
Z = 4	0.13 × 0.11 × 0.09 mm

Data collection

Bruker APEX CCD area-detector diffractometer	5192 independent reflections
Radiation source: fine-focus sealed tube	3606 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.046
ω scans	θmax = 28.3°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
Tmin = 0.85, Tmax = 0.88	k = −22→11
13208 measured reflections	l = −20→21

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.136	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ^2(Fo^2) + (0.069P)^2] where P = (Fo^2 + 2Fc^2)/3
5192 reflections	(Δ/σ)max = 0.001
322 parameters	Δρmax = 0.53 e Å^−3
3 restraints	Δρmin = −0.76 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Co1	0.91070 (5)	0.18840 (2)	0.78370 (2)	0.02526 (13)
C1	0.9365 (4)	0.31872 (16)	0.58113 (17)	0.0268 (6)
C2	1.0894 (4)	0.36035 (17)	0.57876 (16)	0.0280 (6)
H2	1.1715	0.3605	0.6233	0.034*
C3	1.1189 (3)	0.40177 (17)	0.50920 (16)	0.0270 (6)
C4	0.9958 (3)	0.40212 (17)	0.44239 (16)	0.0267 (6)
H4	1.0159	0.4304	0.3963	0.032*
C5	0.8430 (3)	0.36021 (17)	0.44470 (16)	0.0261 (6)
C6	0.8149 (4)	0.31896 (17)	0.51446 (17)	0.0280 (6)
H6	0.7127	0.2910	0.5164	0.034*
C7	0.9062 (4)	0.26952 (17)	0.65377 (17)	0.0295 (6)
C8	1.2853 (4)	0.44426 (18)	0.50588 (17)	0.0321 (7)
C9	0.7107 (4)	0.35829 (17)	0.37216 (16)	0.0291 (6)
C10	0.3481 (4)	−0.02287 (17)	0.62968 (18)	0.0298 (6)
C11	0.2631 (4)	0.04946 (18)	0.61044 (18)	0.0315 (7)
H11	0.2456	0.0857	0.6512	0.038*
C12	0.2038 (4)	0.06864 (18)	0.53144 (18)	0.0322 (7)
C13	0.2269 (4)	0.01358 (19)	0.47063 (19)	0.0359 (7)
H13	0.1864	0.0254	0.4176	0.043*
C14	0.3102 (4)	−0.0589 (2)	0.48938 (19)	0.0389 (7)
H14	0.3265	−0.0954	0.4486	0.047*
C15	0.3694 (4)	−0.07736 (19)	0.56790 (19)	0.0338 (7)
H15	0.4240	−0.1265	0.5798	0.041*
C16	0.4167 (4)	−0.04058 (18)	0.71596 (18)	0.0348 (7)
H16A	0.3418	−0.0165	0.7517	0.042*
H16B	0.4181	−0.0986	0.7247	0.042*
C17	0.1128 (4)	0.1487 (2)	0.5173 (2)	0.0424 (8)
H17A	−0.0070	0.1414	0.5246	0.051*
H17B	0.1610	0.1869	0.5576	0.051*
C18	0.6342 (4)	0.06991 (18)	0.74057 (18)	0.0334 (7)
H18	0.5559	0.1122	0.7343	0.040*
C19	0.7410 (4)	−0.05168 (19)	0.74705 (17)	0.0350 (7)
H19	0.7518	−0.1077	0.7463	0.042*
C20	0.8687 (4)	0.00252 (18)	0.76034 (19)	0.0354 (7)
H20	0.9845	−0.0100	0.7706	0.042*
C21	0.2584 (4)	0.22522 (18)	0.41509 (18)	0.0315 (6)
H21	0.3587	0.2352	0.4486	0.038*
C22	0.0010 (4)	0.18314 (19)	0.3727 (2)	0.0370 (7)
H22	−0.1069	0.1596	0.3705	0.044*
C23	0.0662 (4)	0.22343 (19)	0.31230 (19)	0.0347 (7)
H23	0.0103	0.2319	0.2610	0.042*
N1	0.8011 (3)	0.07952 (15)	0.75631 (14)	0.0309 (5)
N2	0.5918 (3)	−0.00812 (14)	0.73483 (14)	0.0293 (5)
N3	0.1237 (3)	0.18368 (15)	0.43720 (16)	0.0343 (6)
N4	0.2298 (3)	0.24994 (14)	0.33969 (14)	0.0278 (5)
O1	0.7668 (3)	0.23374 (14)	0.65682 (13)	0.0428 (6)
O2	1.0259 (3)	0.26347 (13)	0.71064 (12)	0.0371 (5)
O3	1.4018 (3)	0.43829 (16)	0.56198 (14)	0.0511 (6)
O4	1.2972 (3)	0.48619 (14)	0.44202 (13)	0.0450 (6)
H4A	1.3920	0.5075	0.4448	0.068*
O5	0.7363 (3)	0.39334 (15)	0.30987 (12)	0.0443 (6)
O6	0.5753 (3)	0.31807 (13)	0.38107 (13)	0.0372 (5)
O1W	0.4422 (6)	0.2569 (4)	0.5980 (4)	0.1444 (18)
H1A	0.559 (4)	0.247 (5)	0.610 (6)	0.217*
H1B	0.436 (11)	0.3110 (17)	0.588 (6)	0.217*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Co1	0.0260 (2)	0.0274 (2)	0.0221 (2)	−0.00004 (16)	0.00142 (15)	0.00103 (15)
C1	0.0325 (15)	0.0245 (15)	0.0236 (14)	−0.0015 (11)	0.0038 (12)	0.0011 (11)
C2	0.0306 (15)	0.0314 (16)	0.0215 (14)	−0.0007 (12)	0.0004 (11)	0.0005 (11)
C3	0.0266 (14)	0.0291 (15)	0.0256 (15)	−0.0028 (11)	0.0041 (11)	−0.0011 (11)
C4	0.0309 (15)	0.0278 (15)	0.0218 (14)	−0.0019 (12)	0.0037 (11)	0.0037 (11)
C5	0.0279 (14)	0.0277 (15)	0.0225 (14)	−0.0027 (11)	0.0021 (11)	0.0004 (11)
C6	0.0294 (15)	0.0301 (16)	0.0243 (14)	−0.0047 (12)	0.0022 (12)	−0.0010 (11)
C7	0.0393 (17)	0.0258 (15)	0.0242 (15)	−0.0006 (12)	0.0073 (12)	0.0025 (11)
C8	0.0366 (16)	0.0341 (17)	0.0262 (15)	−0.0057 (13)	0.0056 (13)	−0.0011 (12)
C9	0.0306 (15)	0.0314 (16)	0.0243 (15)	−0.0008 (12)	−0.0010 (12)	−0.0018 (12)
C10	0.0276 (15)	0.0259 (15)	0.0364 (17)	−0.0063 (11)	0.0060 (12)	0.0002 (12)
C11	0.0348 (16)	0.0275 (16)	0.0331 (16)	−0.0043 (12)	0.0079 (13)	−0.0022 (12)
C12	0.0295 (15)	0.0317 (16)	0.0365 (17)	−0.0035 (12)	0.0089 (13)	0.0045 (13)
C13	0.0352 (16)	0.0417 (19)	0.0312 (17)	−0.0066 (14)	0.0051 (13)	0.0014 (13)
C14	0.0384 (17)	0.0385 (19)	0.0414 (19)	−0.0047 (14)	0.0115 (15)	−0.0089 (14)
C15	0.0282 (15)	0.0305 (16)	0.0434 (18)	−0.0009 (12)	0.0073 (13)	−0.0041 (13)
C16	0.0385 (17)	0.0290 (16)	0.0369 (17)	−0.0050 (13)	0.0045 (14)	0.0038 (13)
C17	0.0408 (18)	0.045 (2)	0.044 (2)	0.0059 (15)	0.0176 (15)	0.0125 (15)
C18	0.0359 (17)	0.0256 (16)	0.0373 (17)	0.0034 (12)	−0.0019 (13)	0.0000 (12)
C19	0.0400 (18)	0.0276 (17)	0.0373 (17)	0.0057 (13)	0.0032 (14)	−0.0014 (13)
C20	0.0348 (17)	0.0324 (17)	0.0388 (17)	0.0069 (13)	0.0036 (13)	−0.0017 (13)
C21	0.0261 (15)	0.0322 (16)	0.0362 (17)	0.0004 (12)	0.0033 (12)	0.0010 (13)
C22	0.0245 (15)	0.0405 (19)	0.0454 (19)	−0.0068 (13)	0.0017 (13)	0.0048 (14)
C23	0.0289 (16)	0.0371 (18)	0.0374 (17)	−0.0015 (13)	0.0002 (13)	0.0003 (13)
N1	0.0325 (13)	0.0291 (14)	0.0303 (13)	−0.0005 (10)	−0.0002 (10)	0.0002 (10)
N2	0.0329 (13)	0.0232 (13)	0.0313 (13)	−0.0001 (10)	0.0021 (10)	−0.0018 (10)
N3	0.0304 (13)	0.0325 (14)	0.0412 (16)	−0.0005 (11)	0.0088 (11)	0.0078 (11)
N4	0.0252 (12)	0.0279 (13)	0.0305 (13)	−0.0006 (10)	0.0037 (10)	0.0000 (10)
O1	0.0420 (13)	0.0486 (14)	0.0372 (13)	−0.0145 (11)	0.0020 (10)	0.0138 (10)
O2	0.0379 (12)	0.0453 (14)	0.0268 (11)	−0.0039 (10)	−0.0021 (9)	0.0091 (9)
O3	0.0370 (13)	0.0736 (18)	0.0401 (14)	−0.0219 (12)	−0.0072 (11)	0.0147 (12)
O4	0.0385 (12)	0.0586 (15)	0.0377 (13)	−0.0183 (11)	0.0027 (10)	0.0104 (11)
O5	0.0459 (13)	0.0598 (15)	0.0258 (12)	−0.0092 (11)	−0.0016 (10)	0.0140 (10)
O6	0.0311 (11)	0.0514 (14)	0.0279 (11)	−0.0125 (10)	−0.0025 (9)	0.0017 (9)
O1W	0.109 (3)	0.190 (5)	0.132 (4)	0.003 (4)	0.006 (3)	0.019 (4)

Geometric parameters (Å, º)

Co1—O6^i	1.968 (2)	C14—C15	1.379 (4)
Co1—O2	2.024 (2)	C14—H14	0.9300
Co1—N1	2.026 (2)	C15—H15	0.9300
Co1—N4^i	2.057 (2)	C16—N2	1.477 (4)
C1—C6	1.386 (4)	C16—H16A	0.9700
C1—C2	1.388 (4)	C16—H16B	0.9700
C1—C7	1.503 (4)	C17—N3	1.471 (4)
C2—C3	1.392 (4)	C17—H17A	0.9700
C2—H2	0.9300	C17—H17B	0.9700
C3—C4	1.395 (4)	C18—N1	1.318 (4)
C3—C8	1.490 (4)	C18—N2	1.333 (4)
C4—C5	1.390 (4)	C18—H18	0.9300
C4—H4	0.9300	C19—C20	1.345 (4)
C5—C6	1.390 (4)	C19—N2	1.371 (4)
C5—C9	1.508 (4)	C19—H19	0.9300
C6—H6	0.9300	C20—N1	1.378 (4)
C7—O1	1.250 (3)	C20—H20	0.9300
C7—O2	1.266 (4)	C21—N4	1.322 (4)
C8—O3	1.240 (4)	C21—N3	1.346 (4)
C8—O4	1.286 (3)	C21—H21	0.9300
C9—O5	1.228 (3)	C22—C23	1.356 (4)
C9—O6	1.277 (3)	C22—N3	1.366 (4)
C10—C11	1.390 (4)	C22—H22	0.9300
C10—C15	1.395 (4)	C23—N4	1.387 (4)
C10—C16	1.513 (4)	C23—H23	0.9300
C11—C12	1.389 (4)	N4—Co1^ii	2.057 (2)
C11—H11	0.9300	O4—H4A	0.8200
C12—C13	1.392 (4)	O6—Co1^ii	1.968 (2)
C12—C17	1.511 (4)	O1W—H1A	0.93 (2)
C13—C14	1.384 (4)	O1W—H1B	0.91 (2)
C13—H13	0.9300
O6^i—Co1—O2	103.70 (9)	C14—C15—H15	119.7
O6^i—Co1—N1	111.27 (9)	C10—C15—H15	119.7
O2—Co1—N1	127.96 (9)	N2—C16—C10	111.0 (2)
O6^i—Co1—N4^i	94.21 (9)	N2—C16—H16A	109.4
O2—Co1—N4^i	110.41 (9)	C10—C16—H16A	109.4
N1—Co1—N4^i	104.23 (9)	N2—C16—H16B	109.4
C6—C1—C2	119.8 (3)	C10—C16—H16B	109.4
C6—C1—C7	119.7 (3)	H16A—C16—H16B	108.0
C2—C1—C7	120.4 (3)	N3—C17—C12	114.4 (3)
C1—C2—C3	119.5 (3)	N3—C17—H17A	108.7
C1—C2—H2	120.3	C12—C17—H17A	108.7
C3—C2—H2	120.3	N3—C17—H17B	108.7
C2—C3—C4	120.5 (3)	C12—C17—H17B	108.7
C2—C3—C8	119.4 (3)	H17A—C17—H17B	107.6
C4—C3—C8	120.1 (2)	N1—C18—N2	111.5 (3)
C5—C4—C3	120.0 (2)	N1—C18—H18	124.3
C5—C4—H4	120.0	N2—C18—H18	124.3
C3—C4—H4	120.0	C20—C19—N2	106.5 (3)
C4—C5—C6	119.0 (3)	C20—C19—H19	126.7
C4—C5—C9	120.5 (2)	N2—C19—H19	126.7
C6—C5—C9	120.4 (2)	C19—C20—N1	109.3 (3)
C1—C6—C5	121.2 (3)	C19—C20—H20	125.3
C1—C6—H6	119.4	N1—C20—H20	125.3
C5—C6—H6	119.4	N4—C21—N3	111.4 (3)
O1—C7—O2	120.9 (3)	N4—C21—H21	124.3
O1—C7—C1	120.5 (3)	N3—C21—H21	124.3
O2—C7—C1	118.7 (3)	C23—C22—N3	107.1 (3)
O3—C8—O4	123.8 (3)	C23—C22—H22	126.4
O3—C8—C3	120.7 (3)	N3—C22—H22	126.4
O4—C8—C3	115.5 (3)	C22—C23—N4	108.7 (3)
O5—C9—O6	124.1 (3)	C22—C23—H23	125.6
O5—C9—C5	120.7 (3)	N4—C23—H23	125.6
O6—C9—C5	115.2 (2)	C18—N1—C20	105.5 (2)
C11—C10—C15	118.5 (3)	C18—N1—Co1	122.7 (2)
C11—C10—C16	119.9 (3)	C20—N1—Co1	131.2 (2)
C15—C10—C16	121.5 (3)	C18—N2—C19	107.1 (2)
C12—C11—C10	121.2 (3)	C18—N2—C16	125.9 (2)
C12—C11—H11	119.4	C19—N2—C16	126.9 (2)
C10—C11—H11	119.4	C21—N3—C22	107.0 (3)
C11—C12—C13	119.3 (3)	C21—N3—C17	125.3 (3)
C11—C12—C17	116.9 (3)	C22—N3—C17	127.6 (3)
C13—C12—C17	123.8 (3)	C21—N4—C23	105.7 (2)
C14—C13—C12	119.8 (3)	C21—N4—Co1^ii	122.36 (19)
C14—C13—H13	120.1	C23—N4—Co1^ii	131.9 (2)
C12—C13—H13	120.1	C7—O2—Co1	99.08 (17)
C15—C14—C13	120.6 (3)	C8—O4—H4A	109.5
C15—C14—H14	119.7	C9—O6—Co1^ii	114.27 (18)
C13—C14—H14	119.7	H1A—O1W—H1B	104 (4)
C14—C15—C10	120.5 (3)
C6—C1—C2—C3	−0.1 (4)	C13—C12—C17—N3	−28.7 (4)
C7—C1—C2—C3	176.4 (3)	N2—C19—C20—N1	−0.2 (3)
C1—C2—C3—C4	0.4 (4)	N3—C22—C23—N4	−0.6 (4)
C1—C2—C3—C8	−178.1 (3)	N2—C18—N1—C20	0.3 (3)
C2—C3—C4—C5	−0.6 (4)	N2—C18—N1—Co1	−171.73 (18)
C8—C3—C4—C5	177.9 (3)	C19—C20—N1—C18	−0.1 (3)
C3—C4—C5—C6	0.6 (4)	C19—C20—N1—Co1	171.1 (2)
C3—C4—C5—C9	−178.4 (2)	O6^i—Co1—N1—C18	130.6 (2)
C2—C1—C6—C5	0.1 (4)	O2—Co1—N1—C18	−100.6 (2)
C7—C1—C6—C5	−176.4 (3)	N4^i—Co1—N1—C18	30.3 (3)
C4—C5—C6—C1	−0.3 (4)	O6^i—Co1—N1—C20	−39.2 (3)
C9—C5—C6—C1	178.7 (3)	O2—Co1—N1—C20	89.6 (3)
C6—C1—C7—O1	−5.4 (4)	N4^i—Co1—N1—C20	−139.6 (3)
C2—C1—C7—O1	178.1 (3)	N1—C18—N2—C19	−0.5 (3)
C6—C1—C7—O2	172.9 (3)	N1—C18—N2—C16	−178.5 (3)
C2—C1—C7—O2	−3.7 (4)	C20—C19—N2—C18	0.4 (3)
C2—C3—C8—O3	5.2 (4)	C20—C19—N2—C16	178.4 (3)
C4—C3—C8—O3	−173.4 (3)	C10—C16—N2—C18	69.2 (4)
C2—C3—C8—O4	−174.8 (3)	C10—C16—N2—C19	−108.5 (3)
C4—C3—C8—O4	6.6 (4)	N4—C21—N3—C22	−1.1 (3)
C4—C5—C9—O5	0.4 (4)	N4—C21—N3—C17	−179.2 (3)
C6—C5—C9—O5	−178.6 (3)	C23—C22—N3—C21	1.0 (4)
C4—C5—C9—O6	−179.9 (3)	C23—C22—N3—C17	179.0 (3)
C6—C5—C9—O6	1.1 (4)	C12—C17—N3—C21	−80.6 (4)
C15—C10—C11—C12	−1.6 (4)	C12—C17—N3—C22	101.7 (4)
C16—C10—C11—C12	177.8 (3)	N3—C21—N4—C23	0.8 (3)
C10—C11—C12—C13	1.4 (4)	N3—C21—N4—Co1^ii	−177.61 (19)
C10—C11—C12—C17	179.8 (3)	C22—C23—N4—C21	−0.1 (3)
C11—C12—C13—C14	−0.9 (4)	C22—C23—N4—Co1^ii	178.1 (2)
C17—C12—C13—C14	−179.2 (3)	O1—C7—O2—Co1	0.7 (3)
C12—C13—C14—C15	0.6 (4)	C1—C7—O2—Co1	−177.5 (2)
C13—C14—C15—C10	−0.8 (4)	O6^i—Co1—O2—C7	−174.51 (17)
C11—C10—C15—C14	1.3 (4)	N1—Co1—O2—C7	53.9 (2)
C16—C10—C15—C14	−178.1 (3)	N4^i—Co1—O2—C7	−74.65 (19)
C11—C10—C16—N2	−87.8 (3)	O5—C9—O6—Co1^ii	2.9 (4)
C15—C10—C16—N2	91.4 (3)	C5—C9—O6—Co1^ii	−176.79 (18)
C11—C12—C17—N3	152.9 (3)

Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) x−1/2, −y+1/2, z−1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1A···O1	0.93 (2)	1.74 (3)	2.657 (5)	166 (9)
O4—H4A···O3^iii	0.82	1.87	2.680 (3)	173

Symmetry code: (iii) −x+3, −y+1, −z+1.