Cd^II and Co^II coordination polymers constructed from benzene-1,4-di­car­boxy­lic acid and 2-(pyridin-3-yl)-1H-benzimidazole ligands

In poly[aqua­(μ₃-benzene-1,4-di­carboxyl­ato-κ⁵O¹,O^1′:O¹:O⁴,O^4′)[2-(pyridin-3-yl-κN)-1H-benzimidazole]­cadmium(II)], [Cd(C₈H₄O₄)(C₁₂H₉N₃)(H₂O)]_n, (I), each Cd^II ion is seven-coordinated by the pyridine N atom from a 2-(pyridin-3-yl)benzimidazole (3-PyBIm) ligand, five O atoms from three benzene-1,4-di­carboxyl­ate (1,4-bdc) ligands and one O atom from a coordinated water mol­ecule. The complex forms an extended two-dimensional carboxyl­ate layer structure, which is further extended into a three-dimensional network by hydrogen-bonding inter­actions. In catena-poly[[di­aqua­bis­[2-(pyridin-3-yl-κN)-1H-benzimidazole]­cobalt(II)]-μ₂-benzene-1,4-di­carboxyl­ato-κ²O¹:O⁴], [Co(C₈H₄O₄)(C₁₂H₉N₃)₂(H₂O)₂]_n, (II), each Co^II ion is six-coordinated by two pyridine N atoms from two 3-PyBIm ligands, two O atoms from two 1,4-bdc ligands and two O atoms from two coordinated water mol­ecules. The complex forms a one-dimensional chain-like coordination polymer and is further assembled by hydrogen-bonding inter­actions to form a three-dimensional network.

Computing details

For both structures, data collection: SMART (Bruker, 2007); cell refinement: SMART (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2010); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Poly[aqua(µ₃-benzene-1,4-dicarboxylato-κ⁵O¹,O^1':O¹:O⁴,O^4')[2-(pyridin-3-yl-κN)-1H-benzimidazole]cadmium(II)] (I)

Crystal data

[Cd(C8H4O4)(C12H9N3)(H2O)]	F(000) = 976
Mr = 489.75	Dx = 1.828 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3841 reflections
a = 13.409 (4) Å	θ = 2.8–27.5°
b = 8.564 (2) Å	µ = 1.27 mm^−1
c = 15.535 (4) Å	T = 293 K
β = 93.842 (5)°	Prism, colourless
V = 1779.9 (8) Å^3	0.45 × 0.26 × 0.15 mm
Z = 4

Data collection

Bruker SMART CCD diffractometer	4023 independent reflections
Radiation source: fine-focus sealed tube	3841 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
ω scan	θmax = 27.5°, θmin = 2.8°
Absorption correction: multi-scan (SMART; Bruker, 2007)	h = −17→15
Tmin = 0.680, Tmax = 0.827	k = −11→11
13592 measured reflections	l = −20→20

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.075	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0393P)^2 + 0.9466P] where P = (Fo^2 + 2Fc^2)/3
4023 reflections	(Δ/σ)max = 0.002
268 parameters	Δρmax = 0.52 e Å^−3
3 restraints	Δρmin = −0.99 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
Cd1	0.293891 (11)	0.558154 (16)	0.767509 (9)	0.02385 (7)
O1	0.19962 (14)	0.53836 (19)	0.63920 (12)	0.0352 (4)
O2	0.18640 (13)	0.32610 (18)	0.71750 (10)	0.0298 (3)
O3	−0.18044 (13)	0.05478 (17)	0.40634 (11)	0.0302 (4)
O4	−0.07850 (13)	0.1307 (2)	0.30955 (10)	0.0331 (4)
O5	0.14237 (15)	0.6517 (2)	0.82000 (15)	0.0487 (5)
H5B	0.119 (3)	0.711 (4)	0.7807 (18)	0.073*
H5C	0.092 (2)	0.626 (4)	0.848 (2)	0.073*
N1	0.42025 (15)	0.6116 (2)	0.66474 (13)	0.0322 (4)
N2	0.46000 (15)	0.8901 (2)	0.39671 (12)	0.0293 (4)
N3	0.31936 (16)	0.9232 (2)	0.46375 (14)	0.0322 (4)
H3B	0.2771	0.9156	0.5028	0.039*
C1	0.5124 (2)	0.5528 (3)	0.66422 (18)	0.0350 (6)
H1A	0.5338	0.4836	0.7077	0.042*
C2	0.5778 (2)	0.5901 (3)	0.60192 (18)	0.0379 (6)
H2A	0.6418	0.5479	0.6044	0.045*
C3	0.54633 (19)	0.6909 (3)	0.53603 (16)	0.0347 (5)
H3A	0.5886	0.7168	0.4931	0.042*
C4	0.45020 (17)	0.7529 (2)	0.53518 (14)	0.0279 (4)
C5	0.39073 (18)	0.7102 (3)	0.60128 (15)	0.0320 (5)
H5A	0.3269	0.7525	0.6014	0.038*
C6	0.41171 (17)	0.8564 (3)	0.46564 (14)	0.0278 (4)
C7	0.39494 (18)	0.9845 (3)	0.34650 (15)	0.0290 (5)
C8	0.4063 (2)	1.0528 (3)	0.26649 (18)	0.0371 (6)
H8A	0.4651	1.0408	0.2386	0.045*
C9	0.3275 (2)	1.1389 (3)	0.22991 (18)	0.0447 (6)
H9A	0.3331	1.1843	0.1761	0.054*
C10	0.2399 (2)	1.1592 (3)	0.2718 (2)	0.0470 (7)
H10A	0.1885	1.2189	0.2456	0.056*
C11	0.2273 (2)	1.0932 (3)	0.35119 (19)	0.0416 (6)
H11A	0.1686	1.1068	0.3791	0.050*
C12	0.30651 (18)	1.0051 (3)	0.38776 (15)	0.0307 (5)
C13	0.16496 (17)	0.4043 (3)	0.64969 (14)	0.0255 (4)
C14	0.09375 (16)	0.3380 (2)	0.58105 (13)	0.0235 (4)
C15	0.10050 (18)	0.3789 (3)	0.49481 (14)	0.0291 (5)
H15A	0.1486	0.4503	0.4796	0.035*
C16	0.03572 (17)	0.3135 (3)	0.43177 (14)	0.0280 (5)
H16A	0.0418	0.3384	0.3741	0.034*
C17	−0.03891 (16)	0.2100 (2)	0.45426 (13)	0.0230 (4)
C18	−0.04719 (17)	0.1737 (2)	0.54035 (14)	0.0257 (4)
H18A	−0.0980	0.1077	0.5560	0.031*
C19	0.01980 (16)	0.2350 (2)	0.60334 (13)	0.0249 (4)
H19A	0.0152	0.2070	0.6608	0.030*
C20	−0.10392 (17)	0.1298 (2)	0.38590 (14)	0.0257 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cd1	0.02452 (12)	0.02451 (11)	0.02176 (11)	−0.00114 (5)	−0.00412 (7)	0.00222 (5)
O1	0.0388 (10)	0.0310 (8)	0.0339 (9)	−0.0103 (7)	−0.0104 (8)	0.0005 (6)
O2	0.0336 (9)	0.0274 (8)	0.0270 (8)	0.0028 (6)	−0.0079 (7)	−0.0002 (6)
O3	0.0251 (9)	0.0351 (9)	0.0297 (9)	−0.0039 (6)	−0.0040 (7)	−0.0073 (6)
O4	0.0368 (9)	0.0402 (9)	0.0217 (8)	0.0003 (7)	−0.0012 (7)	−0.0073 (7)
O5	0.0367 (11)	0.0529 (11)	0.0587 (13)	0.0124 (9)	0.0191 (9)	0.0215 (10)
N1	0.0294 (10)	0.0361 (10)	0.0314 (10)	0.0020 (8)	0.0024 (8)	0.0067 (8)
N2	0.0287 (10)	0.0315 (9)	0.0282 (10)	0.0016 (8)	0.0062 (8)	0.0023 (8)
N3	0.0294 (11)	0.0376 (10)	0.0305 (11)	0.0046 (8)	0.0094 (9)	0.0055 (8)
C1	0.0339 (14)	0.0349 (13)	0.0356 (14)	0.0036 (9)	−0.0032 (11)	0.0044 (9)
C2	0.0270 (13)	0.0444 (13)	0.0425 (15)	0.0060 (10)	0.0046 (11)	0.0032 (11)
C3	0.0295 (12)	0.0405 (13)	0.0347 (12)	0.0002 (10)	0.0066 (10)	0.0019 (10)
C4	0.0287 (11)	0.0268 (10)	0.0282 (11)	−0.0004 (8)	0.0017 (9)	−0.0010 (8)
C5	0.0290 (12)	0.0362 (11)	0.0310 (11)	0.0040 (9)	0.0046 (9)	0.0060 (9)
C6	0.0270 (11)	0.0280 (10)	0.0286 (11)	−0.0016 (8)	0.0039 (9)	−0.0022 (8)
C7	0.0330 (12)	0.0270 (10)	0.0273 (11)	−0.0027 (9)	0.0051 (9)	−0.0006 (9)
C8	0.0420 (16)	0.0387 (13)	0.0317 (13)	−0.0025 (10)	0.0097 (12)	0.0050 (9)
C9	0.0529 (17)	0.0458 (14)	0.0354 (14)	−0.0036 (13)	0.0029 (12)	0.0128 (11)
C10	0.0412 (15)	0.0442 (14)	0.0552 (17)	0.0029 (12)	0.0001 (13)	0.0205 (13)
C11	0.0325 (14)	0.0418 (13)	0.0513 (16)	0.0055 (11)	0.0096 (12)	0.0134 (12)
C12	0.0327 (12)	0.0275 (11)	0.0326 (12)	−0.0019 (9)	0.0072 (9)	0.0039 (9)
C13	0.0218 (11)	0.0290 (10)	0.0252 (10)	0.0028 (8)	−0.0020 (8)	−0.0048 (8)
C14	0.0233 (10)	0.0227 (9)	0.0239 (10)	0.0027 (8)	−0.0029 (8)	−0.0031 (7)
C15	0.0301 (12)	0.0291 (10)	0.0280 (11)	−0.0048 (9)	−0.0001 (9)	0.0015 (8)
C16	0.0293 (12)	0.0327 (11)	0.0220 (10)	−0.0018 (9)	0.0012 (9)	0.0003 (8)
C17	0.0227 (10)	0.0237 (9)	0.0222 (10)	0.0036 (8)	−0.0024 (8)	−0.0044 (8)
C18	0.0225 (10)	0.0281 (10)	0.0264 (10)	−0.0036 (8)	0.0006 (8)	−0.0012 (8)
C19	0.0257 (11)	0.0291 (10)	0.0195 (9)	−0.0001 (8)	−0.0006 (8)	−0.0003 (8)
C20	0.0260 (11)	0.0249 (10)	0.0253 (10)	0.0061 (8)	−0.0039 (8)	−0.0049 (8)

Geometric parameters (Å, º)

Cd1—O1	2.2939 (18)	C3—C4	1.393 (3)
Cd1—O2^i	2.3198 (17)	C3—H3A	0.9300
Cd1—O3^ii	2.3677 (17)	C4—C5	1.391 (3)
Cd1—O5	2.378 (2)	C4—C6	1.464 (3)
Cd1—O4^ii	2.4124 (18)	C5—H5A	0.9300
Cd1—N1	2.448 (2)	C7—C8	1.391 (3)
Cd1—O2	2.5456 (17)	C7—C12	1.396 (3)
Cd1—C20^ii	2.741 (2)	C8—C9	1.379 (4)
O1—C13	1.253 (3)	C8—H8A	0.9300
O2—C13	1.265 (3)	C9—C10	1.392 (4)
O2—Cd1^iii	2.3198 (17)	C9—H9A	0.9300
O3—C20	1.269 (3)	C10—C11	1.377 (4)
O3—Cd1^iv	2.3677 (17)	C10—H10A	0.9300
O4—C20	1.256 (3)	C11—C12	1.393 (4)
O4—Cd1^iv	2.4124 (18)	C11—H11A	0.9300
O5—H5B	0.841 (18)	C13—C14	1.495 (3)
O5—H5C	0.863 (18)	C14—C19	1.388 (3)
N1—C1	1.335 (3)	C14—C15	1.394 (3)
N1—C5	1.338 (3)	C15—C16	1.383 (3)
N2—C6	1.320 (3)	C15—H15A	0.9300
N2—C7	1.390 (3)	C16—C17	1.399 (3)
N3—C6	1.363 (3)	C16—H16A	0.9300
N3—C12	1.374 (3)	C17—C18	1.385 (3)
N3—H3B	0.8600	C17—C20	1.495 (3)
C1—C2	1.386 (4)	C18—C19	1.386 (3)
C1—H1A	0.9300	C18—H18A	0.9300
C2—C3	1.383 (4)	C19—H19A	0.9300
C2—H2A	0.9300	C20—Cd1^iv	2.741 (2)
O1—Cd1—O2^i	102.28 (6)	C5—C4—C6	120.8 (2)
O1—Cd1—O3^ii	143.07 (6)	C3—C4—C6	121.2 (2)
O2^i—Cd1—O3^ii	107.70 (6)	N1—C5—C4	123.7 (2)
O1—Cd1—O5	83.64 (8)	N1—C5—H5A	118.2
O2^i—Cd1—O5	74.13 (7)	C4—C5—H5A	118.2
O3^ii—Cd1—O5	84.30 (7)	N2—C6—N3	112.7 (2)
O1—Cd1—O4^ii	121.69 (6)	N2—C6—C4	124.3 (2)
O2^i—Cd1—O4^ii	124.19 (6)	N3—C6—C4	123.0 (2)
O3^ii—Cd1—O4^ii	54.72 (6)	N2—C7—C8	130.1 (2)
O5—Cd1—O4^ii	137.70 (6)	N2—C7—C12	109.6 (2)
O1—Cd1—N1	79.18 (7)	C8—C7—C12	120.3 (2)
O2^i—Cd1—N1	78.54 (7)	C9—C8—C7	117.8 (3)
O3^ii—Cd1—N1	127.29 (7)	C9—C8—H8A	121.1
O5—Cd1—N1	143.63 (7)	C7—C8—H8A	121.1
O4^ii—Cd1—N1	78.03 (6)	C8—C9—C10	121.4 (2)
O1—Cd1—O2	53.80 (5)	C8—C9—H9A	119.3
O2^i—Cd1—O2	149.45 (3)	C10—C9—H9A	119.3
O3^ii—Cd1—O2	90.22 (5)	C11—C10—C9	121.7 (3)
O5—Cd1—O2	83.59 (7)	C11—C10—H10A	119.1
O4^ii—Cd1—O2	86.34 (6)	C9—C10—H10A	119.1
N1—Cd1—O2	110.45 (6)	C10—C11—C12	116.8 (3)
O1—Cd1—C20^ii	139.57 (6)	C10—C11—H11A	121.6
O2^i—Cd1—C20^ii	117.71 (6)	C12—C11—H11A	121.6
O3^ii—Cd1—C20^ii	27.54 (6)	N3—C12—C11	132.5 (2)
O5—Cd1—C20^ii	111.58 (7)	N3—C12—C7	105.6 (2)
O4^ii—Cd1—C20^ii	27.27 (6)	C11—C12—C7	122.0 (2)
N1—Cd1—C20^ii	102.17 (7)	O1—C13—O2	121.9 (2)
O2—Cd1—C20^ii	89.64 (6)	O1—C13—C14	118.7 (2)
C13—O1—Cd1	98.18 (14)	O2—C13—C14	119.4 (2)
C13—O2—Cd1^iii	128.71 (14)	C19—C14—C15	119.54 (19)
C13—O2—Cd1	86.16 (13)	C19—C14—C13	119.76 (19)
Cd1^iii—O2—Cd1	133.10 (7)	C15—C14—C13	120.7 (2)
C20—O3—Cd1^iv	92.84 (13)	C16—C15—C14	120.0 (2)
C20—O4—Cd1^iv	91.10 (14)	C16—C15—H15A	120.0
Cd1—O5—H5B	104 (2)	C14—C15—H15A	120.0
Cd1—O5—H5C	144 (3)	C15—C16—C17	120.4 (2)
H5B—O5—H5C	105 (2)	C15—C16—H16A	119.8
C1—N1—C5	117.5 (2)	C17—C16—H16A	119.8
C1—N1—Cd1	127.95 (17)	C18—C17—C16	119.25 (19)
C5—N1—Cd1	114.53 (16)	C18—C17—C20	120.2 (2)
C6—N2—C7	105.01 (19)	C16—C17—C20	120.43 (19)
C6—N3—C12	107.1 (2)	C17—C18—C19	120.4 (2)
C6—N3—H3B	126.4	C17—C18—H18A	119.8
C12—N3—H3B	126.4	C19—C18—H18A	119.8
N1—C1—C2	123.1 (2)	C18—C19—C14	120.3 (2)
N1—C1—H1A	118.4	C18—C19—H19A	119.9
C2—C1—H1A	118.4	C14—C19—H19A	119.9
C3—C2—C1	119.0 (2)	O4—C20—O3	121.0 (2)
C3—C2—H2A	120.5	O4—C20—C17	119.1 (2)
C1—C2—H2A	120.5	O3—C20—C17	119.8 (2)
C2—C3—C4	118.7 (2)	O4—C20—Cd1^iv	61.63 (12)
C2—C3—H3A	120.6	O3—C20—Cd1^iv	59.62 (11)
C4—C3—H3A	120.6	C17—C20—Cd1^iv	171.04 (14)
C5—C4—C3	117.9 (2)
O2^i—Cd1—O1—C13	−159.10 (14)	C5—C4—C6—N2	−173.3 (2)
O3^ii—Cd1—O1—C13	−15.3 (2)	C3—C4—C6—N2	5.0 (4)
O5—Cd1—O1—C13	−86.91 (16)	C5—C4—C6—N3	3.8 (3)
O4^ii—Cd1—O1—C13	56.78 (17)	C3—C4—C6—N3	−177.9 (2)
N1—Cd1—O1—C13	125.30 (16)	C6—N2—C7—C8	−179.3 (2)
O2—Cd1—O1—C13	−0.21 (13)	C6—N2—C7—C12	−0.2 (3)
C20^ii—Cd1—O1—C13	29.2 (2)	N2—C7—C8—C9	178.3 (2)
O1—Cd1—O2—C13	0.20 (13)	C12—C7—C8—C9	−0.6 (4)
O2^i—Cd1—O2—C13	44.02 (12)	C7—C8—C9—C10	0.9 (4)
O3^ii—Cd1—O2—C13	171.23 (13)	C8—C9—C10—C11	−0.7 (5)
O5—Cd1—O2—C13	86.99 (14)	C9—C10—C11—C12	0.1 (4)
O4^ii—Cd1—O2—C13	−134.15 (13)	C6—N3—C12—C11	178.9 (3)
N1—Cd1—O2—C13	−58.38 (14)	C6—N3—C12—C7	−0.6 (3)
C20^ii—Cd1—O2—C13	−161.24 (13)	C10—C11—C12—N3	−179.3 (3)
O1—Cd1—O2—Cd1^iii	142.92 (13)	C10—C11—C12—C7	0.2 (4)
O2^i—Cd1—O2—Cd1^iii	−173.26 (11)	N2—C7—C12—N3	0.5 (3)
O3^ii—Cd1—O2—Cd1^iii	−46.05 (10)	C8—C7—C12—N3	179.7 (2)
O5—Cd1—O2—Cd1^iii	−130.29 (11)	N2—C7—C12—C11	−179.1 (2)
O4^ii—Cd1—O2—Cd1^iii	8.57 (9)	C8—C7—C12—C11	0.1 (4)
N1—Cd1—O2—Cd1^iii	84.34 (11)	Cd1—O1—C13—O2	0.4 (2)
C20^ii—Cd1—O2—Cd1^iii	−18.52 (10)	Cd1—O1—C13—C14	178.40 (17)
O1—Cd1—N1—C1	−134.1 (2)	Cd1^iii—O2—C13—O1	−145.82 (19)
O2^i—Cd1—N1—C1	120.9 (2)	Cd1—O2—C13—O1	−0.4 (2)
O3^ii—Cd1—N1—C1	17.2 (2)	Cd1^iii—O2—C13—C14	36.2 (3)
O5—Cd1—N1—C1	162.66 (19)	Cd1—O2—C13—C14	−178.35 (19)
O4^ii—Cd1—N1—C1	−8.1 (2)	O1—C13—C14—C19	−149.1 (2)
O2—Cd1—N1—C1	−89.6 (2)	O2—C13—C14—C19	29.0 (3)
C20^ii—Cd1—N1—C1	4.7 (2)	O1—C13—C14—C15	30.6 (3)
O1—Cd1—N1—C5	44.76 (17)	O2—C13—C14—C15	−151.3 (2)
O2^i—Cd1—N1—C5	−60.29 (17)	C19—C14—C15—C16	−1.9 (3)
O3^ii—Cd1—N1—C5	−163.92 (15)	C13—C14—C15—C16	178.3 (2)
O5—Cd1—N1—C5	−18.5 (3)	C14—C15—C16—C17	2.1 (3)
O4^ii—Cd1—N1—C5	170.72 (18)	C15—C16—C17—C18	0.0 (3)
O2—Cd1—N1—C5	89.28 (18)	C15—C16—C17—C20	−175.3 (2)
C20^ii—Cd1—N1—C5	−176.51 (17)	C16—C17—C18—C19	−2.2 (3)
C5—N1—C1—C2	0.4 (4)	C20—C17—C18—C19	173.12 (19)
Cd1—N1—C1—C2	179.23 (19)	C17—C18—C19—C14	2.3 (3)
N1—C1—C2—C3	−1.1 (4)	C15—C14—C19—C18	−0.3 (3)
C1—C2—C3—C4	0.7 (4)	C13—C14—C19—C18	179.5 (2)
C2—C3—C4—C5	0.2 (4)	Cd1^iv—O4—C20—O3	−6.2 (2)
C2—C3—C4—C6	−178.1 (2)	Cd1^iv—O4—C20—C17	169.82 (16)
C1—N1—C5—C4	0.6 (4)	Cd1^iv—O3—C20—O4	6.3 (2)
Cd1—N1—C5—C4	−178.38 (18)	Cd1^iv—O3—C20—C17	−169.66 (16)
C3—C4—C5—N1	−0.9 (4)	C18—C17—C20—O4	−160.8 (2)
C6—C4—C5—N1	177.4 (2)	C16—C17—C20—O4	14.4 (3)
C7—N2—C6—N3	−0.2 (3)	C18—C17—C20—O3	15.2 (3)
C7—N2—C6—C4	177.1 (2)	C16—C17—C20—O3	−169.6 (2)
C12—N3—C6—N2	0.5 (3)	C18—C17—C20—Cd1^iv	−68.8 (11)
C12—N3—C6—C4	−176.8 (2)	C16—C17—C20—Cd1^iv	106.5 (10)

Symmetry codes: (i) −x+1/2, y+1/2, −z+3/2; (ii) x+1/2, −y+1/2, z+1/2; (iii) −x+1/2, y−1/2, −z+3/2; (iv) 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
O5—H5B···O4^v	0.84 (2)	2.00 (2)	2.833 (3)	172 (4)
O5—H5C···N2^vi	0.86 (2)	1.97 (2)	2.814 (3)	166 (3)
N3—H3B···O3^v	0.86	2.00	2.843 (3)	168

Symmetry codes: (v) −x, −y+1, −z+1; (vi) x−1/2, −y+3/2, z+1/2.

catena-Poly[[diaquabis[2-(pyridin-3-yl-κN)-1H-benzimidazole]cobalt(II)]-µ₂-benzene-1,4-dicarboxylato-κ²O¹:O⁴] (II)

Crystal data

[Co(C8H4O4)(C12H9N3)2(H2O)2]	F(000) = 1340
Mr = 649.52	Dx = 1.551 Mg m^−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 5845 reflections
a = 11.460 (2) Å	θ = 2.2–27.5°
b = 16.543 (3) Å	µ = 0.68 mm^−1
c = 14.674 (3) Å	T = 293 K
V = 2781.9 (10) Å^3	Prism, red
Z = 4	0.33 × 0.15 × 0.09 mm

Data collection

Bruker SMART CCD diffractometer	6108 independent reflections
Radiation source: fine-focus sealed tube	5845 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.044
ω scan	θmax = 27.5°, θmin = 2.2°
Absorption correction: multi-scan (SMART; Bruker, 2007)	h = −14→14
Tmin = 0.885, Tmax = 0.941	k = −21→21
21132 measured reflections	l = −19→18

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.108	w = 1/[σ^2(Fo^2) + (0.0527P)^2 + 0.6585P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.002
6108 reflections	Δρmax = 0.49 e Å^−3
419 parameters	Δρmin = −0.68 e Å^−3
7 restraints	Absolute structure: Flack (1983), 2791 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.022 (15)

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	0.37578 (3)	0.247502 (18)	0.05591 (5)	0.03039 (10)
O1	0.19514 (17)	0.26074 (11)	0.04590 (18)	0.0382 (5)
O2	0.13928 (16)	0.28549 (11)	0.18895 (15)	0.0400 (5)
O3	−0.38912 (16)	0.20764 (12)	−0.08089 (15)	0.0411 (5)
O4	−0.44361 (15)	0.23364 (11)	0.06295 (17)	0.0357 (4)
O5	0.39669 (19)	0.27651 (15)	−0.08729 (17)	0.0472 (5)
H5B	0.463 (2)	0.2525 (19)	−0.094 (3)	0.071*
H5C	0.401 (3)	0.3183 (16)	−0.118 (3)	0.071*
O6	0.35977 (17)	0.22207 (13)	0.19963 (16)	0.0412 (4)
H6B	0.294 (2)	0.2378 (19)	0.214 (3)	0.062*
H6C	0.379 (3)	0.1805 (16)	0.228 (2)	0.062*
N1	0.39575 (17)	0.37103 (12)	0.09581 (16)	0.0321 (4)
N2	0.6711 (2)	0.41882 (13)	0.27347 (16)	0.0363 (5)
N3	0.6602 (2)	0.55340 (12)	0.25715 (16)	0.0315 (5)
H3B	0.6351	0.5996	0.2389	0.038*
N4	0.35393 (17)	0.12535 (12)	0.00794 (16)	0.0325 (5)
N5	0.0801 (2)	0.08563 (13)	−0.17704 (17)	0.0345 (5)
N6	0.0903 (2)	−0.04919 (13)	−0.16259 (16)	0.0328 (5)
H6A	0.1155	−0.0958	−0.1456	0.039*
C1	0.3278 (2)	0.43201 (15)	0.06715 (19)	0.0338 (5)
H1A	0.2639	0.4202	0.0305	0.041*
C2	0.3491 (2)	0.51198 (16)	0.0900 (2)	0.0368 (6)
H2A	0.3006	0.5530	0.0690	0.044*
C3	0.4436 (2)	0.52935 (15)	0.1446 (2)	0.0353 (6)
H3A	0.4598	0.5826	0.1606	0.042*
C4	0.5143 (2)	0.46758 (14)	0.17559 (18)	0.0305 (5)
C5	0.4863 (2)	0.38928 (14)	0.14976 (18)	0.0321 (5)
H5A	0.5329	0.3472	0.1710	0.038*
C6	0.6149 (2)	0.47899 (15)	0.23550 (19)	0.0299 (5)
C7	0.7597 (3)	0.45526 (15)	0.3237 (2)	0.0340 (6)
C8	0.8472 (3)	0.41988 (19)	0.3757 (2)	0.0441 (7)
H8A	0.8518	0.3641	0.3826	0.053*
C9	0.9270 (3)	0.4707 (2)	0.4168 (2)	0.0466 (7)
H9A	0.9855	0.4486	0.4529	0.056*
C10	0.9221 (3)	0.55431 (19)	0.4055 (2)	0.0442 (7)
H10A	0.9780	0.5865	0.4338	0.053*
C11	0.8363 (3)	0.59075 (18)	0.3533 (2)	0.0370 (6)
H11A	0.8335	0.6464	0.3449	0.044*
C12	0.7546 (3)	0.53920 (13)	0.3142 (2)	0.0309 (5)
C13	0.4221 (2)	0.06349 (16)	0.03238 (19)	0.0361 (6)
H13A	0.4856	0.0736	0.0701	0.043*
C14	0.4018 (2)	−0.01511 (16)	0.0037 (2)	0.0389 (6)
H14A	0.4506	−0.0569	0.0223	0.047*
C15	0.3079 (3)	−0.03039 (15)	−0.05285 (18)	0.0349 (6)
H15A	0.2921	−0.0827	−0.0724	0.042*
C16	0.2376 (2)	0.03326 (13)	−0.08005 (18)	0.0289 (5)
C17	0.2634 (2)	0.11051 (14)	−0.04695 (19)	0.0339 (5)
H17A	0.2156	0.1534	−0.0639	0.041*
C18	0.1360 (2)	0.02430 (15)	−0.14014 (18)	0.0306 (5)
C19	−0.0102 (3)	0.05031 (15)	−0.2256 (2)	0.0342 (6)
C20	−0.1006 (3)	0.08685 (19)	−0.2747 (2)	0.0421 (6)
H20A	−0.1064	0.1428	−0.2789	0.050*
C21	−0.1802 (3)	0.0372 (2)	−0.3164 (2)	0.0506 (8)
H21A	−0.2409	0.0600	−0.3497	0.061*
C22	−0.1719 (3)	−0.0475 (2)	−0.3098 (2)	0.0526 (8)
H22A	−0.2271	−0.0793	−0.3392	0.063*
C23	−0.0846 (3)	−0.08463 (19)	−0.2611 (2)	0.0457 (7)
H23A	−0.0794	−0.1406	−0.2571	0.055*
C24	−0.0041 (3)	−0.03392 (15)	−0.2179 (2)	0.0344 (6)
C25	0.1188 (2)	0.26930 (16)	0.1072 (2)	0.0338 (6)
C26	−0.0078 (3)	0.25828 (13)	0.0784 (2)	0.0320 (7)
C27	−0.0948 (3)	0.25822 (15)	0.1446 (2)	0.0358 (6)
H27A	−0.0754	0.2644	0.2057	0.043*
C28	−0.2114 (3)	0.24890 (14)	0.1187 (3)	0.0360 (7)
H28A	−0.2695	0.2501	0.1630	0.043*
C29	−0.2416 (3)	0.23791 (14)	0.0284 (2)	0.0327 (6)
C30	−0.1533 (3)	0.23882 (16)	−0.0377 (3)	0.0373 (6)
H30A	−0.1724	0.2330	−0.0989	0.045*
C31	−0.0376 (3)	0.24845 (15)	−0.0121 (3)	0.0383 (7)
H31A	0.0205	0.2483	−0.0563	0.046*
C32	−0.3676 (2)	0.22548 (15)	0.0005 (2)	0.0315 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Co1	0.01657 (17)	0.03111 (16)	0.04349 (19)	−0.00200 (9)	−0.00218 (13)	−0.00415 (12)
O1	0.0163 (9)	0.0426 (9)	0.0558 (15)	−0.0029 (6)	−0.0024 (10)	−0.0074 (9)
O2	0.0244 (9)	0.0392 (10)	0.0563 (13)	−0.0009 (7)	−0.0033 (8)	−0.0085 (9)
O3	0.0281 (9)	0.0452 (11)	0.0500 (12)	−0.0013 (8)	−0.0046 (9)	−0.0053 (9)
O4	0.0170 (8)	0.0428 (8)	0.0473 (11)	−0.0008 (7)	0.0003 (10)	−0.0033 (10)
O5	0.0385 (12)	0.0521 (13)	0.0510 (14)	0.0056 (10)	−0.0068 (10)	0.0072 (11)
O6	0.0315 (11)	0.0413 (11)	0.0508 (13)	0.0057 (8)	0.0024 (9)	0.0052 (10)
N1	0.0245 (10)	0.0320 (10)	0.0397 (12)	−0.0019 (8)	−0.0018 (9)	0.0000 (8)
N2	0.0339 (13)	0.0313 (10)	0.0436 (13)	−0.0031 (9)	−0.0063 (10)	0.0014 (9)
N3	0.0309 (11)	0.0259 (9)	0.0377 (12)	−0.0019 (8)	−0.0025 (10)	−0.0004 (8)
N4	0.0232 (10)	0.0343 (10)	0.0401 (12)	−0.0022 (8)	−0.0013 (9)	−0.0049 (9)
N5	0.0300 (12)	0.0325 (11)	0.0410 (12)	−0.0067 (9)	−0.0026 (10)	0.0015 (9)
N6	0.0322 (11)	0.0278 (10)	0.0383 (12)	−0.0036 (9)	−0.0019 (10)	−0.0031 (8)
C1	0.0243 (11)	0.0413 (12)	0.0357 (13)	0.0006 (9)	−0.0028 (10)	0.0020 (11)
C2	0.0328 (14)	0.0374 (13)	0.0403 (15)	0.0052 (10)	−0.0031 (12)	0.0038 (11)
C3	0.0344 (14)	0.0301 (11)	0.0415 (15)	−0.0021 (10)	−0.0009 (12)	−0.0027 (10)
C4	0.0261 (13)	0.0321 (11)	0.0333 (13)	−0.0040 (9)	−0.0003 (10)	−0.0004 (9)
C5	0.0252 (12)	0.0291 (11)	0.0419 (15)	−0.0016 (9)	−0.0038 (10)	−0.0009 (10)
C6	0.0264 (12)	0.0300 (11)	0.0334 (13)	−0.0034 (9)	−0.0022 (10)	−0.0018 (10)
C7	0.0284 (13)	0.0373 (12)	0.0363 (16)	−0.0028 (11)	−0.0010 (12)	0.0031 (10)
C8	0.0404 (18)	0.0430 (16)	0.0490 (19)	0.0000 (13)	−0.0109 (15)	0.0098 (13)
C9	0.0355 (17)	0.0627 (19)	0.0417 (18)	0.0014 (13)	−0.0137 (14)	0.0021 (13)
C10	0.0339 (16)	0.0541 (17)	0.0447 (17)	−0.0073 (12)	−0.0051 (13)	−0.0098 (13)
C11	0.0338 (15)	0.0383 (13)	0.0389 (15)	−0.0044 (11)	0.0003 (12)	−0.0063 (11)
C12	0.0289 (12)	0.0333 (11)	0.0304 (12)	−0.0033 (11)	0.0027 (10)	−0.0019 (10)
C13	0.0272 (12)	0.0418 (13)	0.0393 (15)	0.0003 (10)	−0.0038 (10)	−0.0029 (10)
C14	0.0345 (15)	0.0369 (13)	0.0453 (16)	0.0073 (11)	−0.0009 (12)	0.0036 (12)
C15	0.0376 (14)	0.0302 (12)	0.0371 (15)	−0.0016 (10)	0.0010 (11)	−0.0008 (9)
C16	0.0275 (12)	0.0282 (11)	0.0310 (12)	−0.0029 (9)	0.0005 (10)	−0.0003 (8)
C17	0.0282 (13)	0.0316 (12)	0.0418 (14)	0.0006 (10)	−0.0035 (11)	−0.0065 (10)
C18	0.0287 (13)	0.0302 (11)	0.0328 (13)	−0.0058 (10)	−0.0003 (11)	−0.0023 (10)
C19	0.0297 (14)	0.0372 (12)	0.0356 (15)	−0.0071 (11)	−0.0006 (11)	−0.0019 (11)
C20	0.0353 (15)	0.0503 (15)	0.0407 (16)	−0.0018 (12)	−0.0005 (13)	0.0057 (13)
C21	0.0387 (18)	0.075 (2)	0.0382 (18)	−0.0079 (15)	−0.0044 (14)	0.0054 (14)
C22	0.0414 (18)	0.074 (2)	0.0428 (19)	−0.0186 (15)	−0.0038 (15)	−0.0089 (15)
C23	0.0451 (18)	0.0476 (16)	0.0443 (17)	−0.0138 (13)	0.0018 (14)	−0.0086 (13)
C24	0.0276 (13)	0.0436 (13)	0.0320 (13)	−0.0068 (11)	−0.0020 (10)	−0.0043 (11)
C25	0.0188 (12)	0.0226 (10)	0.0600 (18)	−0.0019 (9)	−0.0024 (12)	−0.0046 (11)
C26	0.0131 (12)	0.0265 (10)	0.057 (2)	−0.0009 (8)	−0.0023 (12)	−0.0016 (10)
C27	0.0226 (14)	0.0364 (13)	0.0483 (18)	−0.0036 (10)	−0.0071 (14)	−0.0011 (11)
C28	0.0175 (16)	0.0392 (16)	0.0511 (19)	−0.0025 (8)	0.0053 (14)	−0.0023 (10)
C29	0.0216 (13)	0.0251 (9)	0.0513 (18)	−0.0023 (10)	0.0004 (12)	−0.0028 (10)
C30	0.0227 (13)	0.0368 (13)	0.0525 (18)	−0.0011 (11)	0.0033 (14)	−0.0027 (12)
C31	0.0234 (17)	0.0357 (15)	0.056 (2)	−0.0030 (9)	0.0021 (15)	−0.0050 (10)
C32	0.0206 (12)	0.0250 (10)	0.0488 (15)	0.0001 (9)	−0.0027 (11)	0.0009 (10)

Geometric parameters (Å, º)

Co1—O4^i	2.0850 (18)	C8—C9	1.381 (4)
Co1—O1	2.087 (2)	C8—H8A	0.9300
Co1—N1	2.138 (2)	C9—C10	1.394 (5)
Co1—N4	2.154 (2)	C9—H9A	0.9300
Co1—O6	2.158 (2)	C10—C11	1.385 (4)
Co1—O5	2.169 (3)	C10—H10A	0.9300
O1—C25	1.263 (4)	C11—C12	1.391 (4)
O2—C25	1.251 (4)	C11—H11A	0.9300
O3—C32	1.255 (4)	C13—C14	1.386 (4)
O4—C32	1.271 (3)	C13—H13A	0.9300
O4—Co1^ii	2.0850 (18)	C14—C15	1.383 (4)
O5—H5B	0.860 (18)	C14—H14A	0.9300
O5—H5C	0.825 (18)	C15—C16	1.384 (4)
O6—H6B	0.828 (18)	C15—H15A	0.9300
O6—H6C	0.836 (17)	C16—C17	1.399 (3)
N1—C5	1.340 (3)	C16—C18	1.468 (4)
N1—C1	1.342 (3)	C17—H17A	0.9300
N2—C6	1.310 (3)	C19—C20	1.399 (4)
N2—C7	1.392 (4)	C19—C24	1.400 (3)
N3—C6	1.373 (3)	C20—C21	1.372 (4)
N3—C12	1.387 (4)	C20—H20A	0.9300
N3—H3B	0.8600	C21—C22	1.408 (5)
N4—C17	1.336 (3)	C21—H21A	0.9300
N4—C13	1.336 (3)	C22—C23	1.373 (5)
N5—C18	1.316 (3)	C22—H22A	0.9300
N5—C19	1.386 (4)	C23—C24	1.399 (4)
N6—C18	1.364 (3)	C23—H23A	0.9300
N6—C24	1.376 (4)	C25—C26	1.522 (4)
N6—H6A	0.8600	C26—C31	1.380 (5)
C1—C2	1.387 (4)	C26—C27	1.392 (5)
C1—H1A	0.9300	C27—C28	1.398 (4)
C2—C3	1.378 (4)	C27—H27A	0.9300
C2—H2A	0.9300	C28—C29	1.382 (5)
C3—C4	1.381 (4)	C28—H28A	0.9300
C3—H3A	0.9300	C29—C30	1.401 (5)
C4—C5	1.387 (3)	C29—C32	1.516 (4)
C4—C6	1.461 (4)	C30—C31	1.388 (5)
C5—H5A	0.9300	C30—H30A	0.9300
C7—C8	1.389 (4)	C31—H31A	0.9300
C7—C12	1.397 (3)
O4^i—Co1—O1	178.77 (13)	C10—C11—C12	116.1 (3)
O4^i—Co1—N1	89.16 (7)	C10—C11—H11A	122.0
O1—Co1—N1	91.44 (8)	C12—C11—H11A	122.0
O4^i—Co1—N4	91.63 (7)	N3—C12—C11	132.1 (2)
O1—Co1—N4	87.72 (8)	N3—C12—C7	105.1 (2)
N1—Co1—N4	176.76 (11)	C11—C12—C7	122.7 (3)
O4^i—Co1—O6	90.83 (9)	N4—C13—C14	122.6 (2)
O1—Co1—O6	90.28 (9)	N4—C13—H13A	118.7
N1—Co1—O6	85.86 (9)	C14—C13—H13A	118.7
N4—Co1—O6	97.27 (9)	C15—C14—C13	118.9 (2)
O4^i—Co1—O5	87.86 (9)	C15—C14—H14A	120.5
O1—Co1—O5	91.04 (9)	C13—C14—H14A	120.5
N1—Co1—O5	92.41 (9)	C14—C15—C16	119.1 (2)
N4—Co1—O5	84.48 (10)	C14—C15—H15A	120.4
O6—Co1—O5	177.85 (10)	C16—C15—H15A	120.4
C25—O1—Co1	130.4 (2)	C15—C16—C17	118.1 (2)
C32—O4—Co1^ii	131.0 (2)	C15—C16—C18	123.9 (2)
Co1—O5—H5B	96 (3)	C17—C16—C18	117.9 (2)
Co1—O5—H5C	136 (3)	N4—C17—C16	122.8 (2)
H5B—O5—H5C	105 (3)	N4—C17—H17A	118.6
Co1—O6—H6B	106 (3)	C16—C17—H17A	118.6
Co1—O6—H6C	129 (3)	N5—C18—N6	113.6 (2)
H6B—O6—H6C	112 (3)	N5—C18—C16	123.7 (2)
C5—N1—C1	117.7 (2)	N6—C18—C16	122.6 (2)
C5—N1—Co1	117.39 (16)	N5—C19—C20	129.5 (3)
C1—N1—Co1	124.78 (18)	N5—C19—C24	109.9 (2)
C6—N2—C7	104.8 (2)	C20—C19—C24	120.6 (2)
C6—N3—C12	106.4 (2)	C21—C20—C19	117.6 (3)
C6—N3—H3B	126.8	C21—C20—H20A	121.2
C12—N3—H3B	126.8	C19—C20—H20A	121.2
C17—N4—C13	118.3 (2)	C20—C21—C22	121.3 (3)
C17—N4—Co1	117.36 (16)	C20—C21—H21A	119.4
C13—N4—Co1	124.25 (18)	C22—C21—H21A	119.4
C18—N5—C19	104.5 (2)	C23—C22—C21	122.1 (3)
C18—N6—C24	106.3 (2)	C23—C22—H22A	119.0
C18—N6—H6A	126.9	C21—C22—H22A	119.0
C24—N6—H6A	126.9	C22—C23—C24	116.6 (3)
N1—C1—C2	122.6 (2)	C22—C23—H23A	121.7
N1—C1—H1A	118.7	C24—C23—H23A	121.7
C2—C1—H1A	118.7	N6—C24—C23	132.5 (3)
C3—C2—C1	118.6 (2)	N6—C24—C19	105.7 (2)
C3—C2—H2A	120.7	C23—C24—C19	121.8 (3)
C1—C2—H2A	120.7	O2—C25—O1	125.2 (2)
C2—C3—C4	119.9 (2)	O2—C25—C26	118.1 (2)
C2—C3—H3A	120.0	O1—C25—C26	116.7 (3)
C4—C3—H3A	120.0	C31—C26—C27	119.6 (3)
C3—C4—C5	117.7 (2)	C31—C26—C25	121.2 (3)
C3—C4—C6	124.4 (2)	C27—C26—C25	119.3 (3)
C5—C4—C6	117.9 (2)	C26—C27—C28	119.7 (3)
N1—C5—C4	123.4 (2)	C26—C27—H27A	120.1
N1—C5—H5A	118.3	C28—C27—H27A	120.1
C4—C5—H5A	118.3	C29—C28—C27	120.9 (3)
N2—C6—N3	113.3 (2)	C29—C28—H28A	119.5
N2—C6—C4	123.1 (2)	C27—C28—H28A	119.5
N3—C6—C4	123.6 (2)	C28—C29—C30	118.8 (3)
C8—C7—N2	129.4 (2)	C28—C29—C32	121.0 (3)
C8—C7—C12	120.3 (3)	C30—C29—C32	120.1 (3)
N2—C7—C12	110.3 (2)	C31—C30—C29	120.2 (4)
C9—C8—C7	117.5 (3)	C31—C30—H30A	119.9
C9—C8—H8A	121.3	C29—C30—H30A	119.9
C7—C8—H8A	121.3	C26—C31—C30	120.7 (4)
C8—C9—C10	121.7 (3)	C26—C31—H31A	119.6
C8—C9—H9A	119.1	C30—C31—H31A	119.6
C10—C9—H9A	119.1	O3—C32—O4	125.2 (2)
C11—C10—C9	121.7 (3)	O3—C32—C29	118.4 (2)
C11—C10—H10A	119.1	O4—C32—C29	116.4 (3)
C9—C10—H10A	119.1
O4^i—Co1—O1—C25	170 (4)	N2—C7—C12—C11	−176.7 (3)
N1—Co1—O1—C25	−71.3 (2)	C17—N4—C13—C14	−0.6 (4)
N4—Co1—O1—C25	111.9 (2)	Co1—N4—C13—C14	176.6 (2)
O6—Co1—O1—C25	14.6 (2)	N4—C13—C14—C15	0.4 (4)
O5—Co1—O1—C25	−163.7 (2)	C13—C14—C15—C16	0.7 (4)
O4^i—Co1—N1—C5	−30.3 (2)	C14—C15—C16—C17	−1.5 (4)
O1—Co1—N1—C5	150.8 (2)	C14—C15—C16—C18	179.8 (3)
N4—Co1—N1—C5	−134.3 (15)	C13—N4—C17—C16	−0.3 (4)
O6—Co1—N1—C5	60.63 (19)	Co1—N4—C17—C16	−177.8 (2)
O5—Co1—N1—C5	−118.08 (19)	C15—C16—C17—N4	1.4 (4)
O4^i—Co1—N1—C1	146.2 (2)	C18—C16—C17—N4	−179.9 (2)
O1—Co1—N1—C1	−32.7 (2)	C19—N5—C18—N6	1.4 (3)
N4—Co1—N1—C1	42.2 (16)	C19—N5—C18—C16	−178.4 (3)
O6—Co1—N1—C1	−122.9 (2)	C24—N6—C18—N5	−0.8 (3)
O5—Co1—N1—C1	58.4 (2)	C24—N6—C18—C16	179.0 (3)
O4^i—Co1—N4—C17	−149.8 (2)	C15—C16—C18—N5	−169.2 (3)
O1—Co1—N4—C17	29.2 (2)	C17—C16—C18—N5	12.1 (4)
N1—Co1—N4—C17	−45.8 (16)	C15—C16—C18—N6	11.1 (4)
O6—Co1—N4—C17	119.2 (2)	C17—C16—C18—N6	−167.6 (3)
O5—Co1—N4—C17	−62.1 (2)	C18—N5—C19—C20	176.6 (3)
O4^i—Co1—N4—C13	32.9 (2)	C18—N5—C19—C24	−1.4 (3)
O1—Co1—N4—C13	−148.1 (2)	N5—C19—C20—C21	−179.5 (3)
N1—Co1—N4—C13	136.9 (15)	C24—C19—C20—C21	−1.6 (5)
O6—Co1—N4—C13	−58.1 (2)	C19—C20—C21—C22	0.3 (5)
O5—Co1—N4—C13	120.6 (2)	C20—C21—C22—C23	0.4 (5)
C5—N1—C1—C2	1.0 (4)	C21—C22—C23—C24	0.2 (5)
Co1—N1—C1—C2	−175.5 (2)	C18—N6—C24—C23	−179.6 (3)
N1—C1—C2—C3	−0.2 (4)	C18—N6—C24—C19	−0.1 (3)
C1—C2—C3—C4	−0.3 (4)	C22—C23—C24—N6	177.9 (3)
C2—C3—C4—C5	0.0 (4)	C22—C23—C24—C19	−1.5 (5)
C2—C3—C4—C6	−178.4 (3)	N5—C19—C24—N6	1.0 (3)
C1—N1—C5—C4	−1.4 (4)	C20—C19—C24—N6	−177.3 (3)
Co1—N1—C5—C4	175.4 (2)	N5—C19—C24—C23	−179.5 (3)
C3—C4—C5—N1	0.9 (4)	C20—C19—C24—C23	2.3 (4)
C6—C4—C5—N1	179.4 (2)	Co1—O1—C25—O2	13.1 (4)
C7—N2—C6—N3	0.0 (3)	Co1—O1—C25—C26	−166.51 (16)
C7—N2—C6—C4	179.6 (3)	O2—C25—C26—C31	173.4 (2)
C12—N3—C6—N2	0.2 (3)	O1—C25—C26—C31	−7.0 (4)
C12—N3—C6—C4	−179.4 (3)	O2—C25—C26—C27	−6.5 (4)
C3—C4—C6—N2	170.7 (3)	O1—C25—C26—C27	173.1 (2)
C5—C4—C6—N2	−7.7 (4)	C31—C26—C27—C28	−0.5 (4)
C3—C4—C6—N3	−9.7 (4)	C25—C26—C27—C28	179.4 (2)
C5—C4—C6—N3	171.8 (2)	C26—C27—C28—C29	1.4 (4)
C6—N2—C7—C8	−178.3 (3)	C27—C28—C29—C30	−2.0 (4)
C6—N2—C7—C12	−0.2 (3)	C27—C28—C29—C32	178.3 (2)
N2—C7—C8—C9	178.1 (3)	C28—C29—C30—C31	1.7 (4)
C12—C7—C8—C9	0.1 (5)	C32—C29—C30—C31	−178.6 (2)
C7—C8—C9—C10	−1.2 (5)	C27—C26—C31—C30	0.2 (4)
C8—C9—C10—C11	0.7 (5)	C25—C26—C31—C30	−179.7 (2)
C9—C10—C11—C12	1.0 (5)	C29—C30—C31—C26	−0.8 (4)
C6—N3—C12—C11	176.3 (3)	Co1^ii—O4—C32—O3	−15.4 (4)
C6—N3—C12—C7	−0.2 (3)	Co1^ii—O4—C32—C29	165.08 (16)
C10—C11—C12—N3	−178.2 (3)	C28—C29—C32—O3	−172.9 (2)
C10—C11—C12—C7	−2.1 (5)	C30—C29—C32—O3	7.4 (4)
C8—C7—C12—N3	178.6 (3)	C28—C29—C32—O4	6.6 (4)
N2—C7—C12—N3	0.3 (3)	C30—C29—C32—O4	−173.0 (2)
C8—C7—C12—C11	1.6 (5)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6B···O2	0.83 (2)	1.97 (2)	2.740 (3)	154 (4)
O5—H5B···O3^i	0.86 (2)	1.86 (2)	2.708 (3)	166 (5)
O6—H6C···N5^iii	0.84 (2)	2.15 (2)	2.974 (3)	170 (4)
N3—H3B···O2^iv	0.86	2.04	2.857 (3)	159
N6—H6A···O3^v	0.86	2.08	2.892 (3)	157

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