Syntheses, structures and characterization of isomorphous Co^II and Ni^II coordination polymers based on 2-[(1H-imidazol-1-yl)meth­yl]-6-methyl-1H-benz­imidazole and benzene-1,4-di­carboxyl­ate

Careful choice of the organic ligands is one of the most important parameters in the rational design and synthesis of coordination polymers. Aromatic polycarboxyl­ates have been widely used in the preparation of metal–organic polymers since they can utilize various coordination modes to form diverse structures and can act as hydrogen-bond acceptors and donors in the assembly of supra­molecular structures. Nitrogen-heterocyclic organic compounds have also been used extensively as ligands for the construction of polymers with inter­esting structures. In the polymers catena-poly[[[di­aqua­bis­{2-[(1H-imid­azol-1-yl)meth­yl]-6-methyl-1H-benzimidazole-κN³}cobalt(II)]-μ₂-benzene-1,4-di­car­boxyl­ato-κ²O¹:O⁴] dihydrate], {[Co(C₈H₄O₄)(C₁₂H₁₁N₄)₂(H₂O)₂]·2H₂O}_n, (I), and catena-poly[[[di­aqua­bis­{2-[(1H-imidazol-1-yl)meth­yl]-6-methyl-1H-benz­imidazole-κN³}nickel(II)]-μ₂-benzene-1,4-di­carboxyl­ato-κ²O¹:O⁴] dihydrate], {[Ni(C₈H₄O₄)(C₁₂H₁₁N₄)₂(H₂O)₂]·2H₂O}_n, (II), the Co^II or Ni^II ion lies on an inversion centre and exhibits a slightly distorted octa­hedral coordination geometry, coordinated by two N atoms from two imidazole rings and four O atoms from two monodentate carboxyl­ate groups and two water mol­ecules. The di­carboxyl­ate ligands bridge metal ions forming a polymeric chain. The 2-[(1H-imidazol-1-yl)meth­yl]-6-methyl-1H-benzimidazole ligands coordinate to the Co^II or Ni^II centres in monodentate modes through an imidazole N atom and are pendant on opposite sides of the main chain. The two structures are isomorphous. In the crystal, the one-dimensional chains are further connected through O—H...O, O—H...N and N—H...O hydrogen bonds, leading to a three-dimensional supra­molecular architecture. In addition, the IR spectroscopic properties, PXRD patterns, thermogravimetric behaviours and fluorescence properties of both polymers have been investigated.

Computing details

For both structures, data collection: CrystalClear (Rigaku/MSC, 2004); cell refinement: CrystalClear (Rigaku/MSC, 2004); data reduction: CrystalClear (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: publCIF (Westrip, 2010).

catena-Poly[[[diaquabis{2-[(1H-imidazol-1-yl)methyl]-6-methyl-1H-benzimidazole-κN³}cobalt(II)]-µ₂-benzene-1,4-dicarboxylato-κ²O¹:O⁴] dihydrate] (I)

Crystal data

[Co(C8H4O4)(C12H11N4)2(H2O)2]·2H2O	F(000) = 750
Mr = 719.62	Dx = 1.421 Mg m^−3
Monoclinic, P2/n	Mo Kα radiation, λ = 0.71073 Å
a = 13.264 (3) Å	Cell parameters from 4480 reflections
b = 9.0189 (18) Å	θ = 1.8–27.9°
c = 14.709 (3) Å	µ = 0.57 mm^−1
β = 107.04 (3)°	T = 293 K
V = 1682.4 (6) Å^3	Prism, red
Z = 2	0.21 × 0.19 × 0.19 mm

Data collection

Rigaku Saturn diffractometer	3211 independent reflections
Radiation source: fine-focus sealed tube	3047 reflections with I > 2σ(I)
Detector resolution: 28.5714 pixels mm^-1	Rint = 0.034
ω scans	θmax = 25.8°, θmin = 2.3°
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2004)	h = −16→16
Tmin = 0.889, Tmax = 0.899	k = −11→11
17412 measured reflections	l = −17→17

Refinement

Refinement on F^2	42 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.052	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.096	w = 1/[σ^2(Fo^2) + (0.0255P)^2 + 0.9676P] where P = (Fo^2 + 2Fc^2)/3
S = 1.23	(Δ/σ)max < 0.001
3211 reflections	Δρmax = 0.22 e Å^−3
297 parameters	Δρmin = −0.21 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.42634 (19)	0.4319 (3)	0.17111 (18)	0.0393 (6)
C2	0.3515 (2)	0.4301 (3)	0.30938 (18)	0.0475 (6)
H2	0.4200	0.4297	0.3499	0.057*
C3	0.33494 (18)	0.4300 (3)	0.21212 (16)	0.0373 (5)
C4	0.23249 (19)	0.4308 (3)	0.15274 (17)	0.0446 (6)
H4	0.2200	0.4318	0.0871	0.054*
C5	0.5712 (2)	0.8088 (3)	0.09123 (18)	0.0457 (6)
H5	0.6418	0.7883	0.0984	0.055*
C6	0.4041 (2)	0.7894 (3)	0.05659 (19)	0.0531 (7)
H6	0.3361	0.7516	0.0344	0.064*
C7	0.4294 (2)	0.9236 (4)	0.09671 (19)	0.0556 (7)
H7	0.3831	0.9941	0.1075	0.067*
C8	0.6006 (2)	1.0586 (3)	0.16817 (19)	0.0543 (7)
H8A	0.5677	1.1516	0.1423	0.065*
H8B	0.6695	1.0543	0.1578	0.065*
C9	0.6135 (2)	1.0540 (3)	0.27234 (19)	0.0473 (6)
C10	0.6451 (10)	0.9781 (15)	0.4173 (6)	0.047 (2)	0.715 (7)
C10'	0.6207 (18)	1.164 (2)	0.4084 (7)	0.043 (6)	0.285 (7)
C11'	0.641 (2)	1.012 (2)	0.4178 (9)	0.049 (8)	0.285 (7)
C12'	0.6544 (18)	0.9434 (14)	0.5051 (12)	0.051 (5)	0.285 (7)
H12'	0.6679	0.8422	0.5114	0.061*	0.285 (7)
C13'	0.6477 (13)	1.0259 (14)	0.5830 (8)	0.043 (5)	0.285 (7)
C14'	0.6275 (12)	1.1772 (13)	0.5735 (8)	0.051 (5)	0.285 (7)
H14'	0.6230	1.2323	0.6256	0.061*	0.285 (7)
C15'	0.6140 (15)	1.2461 (13)	0.4862 (10)	0.054 (5)	0.285 (7)
H15'	0.6004	1.3473	0.4799	0.065*	0.285 (7)
C11	0.6123 (8)	1.1228 (12)	0.4151 (4)	0.0429 (19)	0.715 (7)
C12	0.6006 (7)	1.1948 (9)	0.4957 (5)	0.0595 (17)	0.715 (7)
H12	0.5784	1.2929	0.4940	0.071*	0.715 (7)
C13	0.6241 (6)	1.1114 (9)	0.5780 (5)	0.0557 (19)	0.715 (7)
C14	0.6576 (8)	0.9661 (9)	0.5785 (6)	0.064 (2)	0.715 (7)
H14	0.6723	0.9133	0.6352	0.076*	0.715 (7)
C15	0.6704 (9)	0.8969 (9)	0.5013 (6)	0.0636 (19)	0.715 (7)
H15	0.6948	0.7998	0.5042	0.076*	0.715 (7)
C16	0.6090 (4)	1.1826 (6)	0.6685 (3)	0.0802 (17)	0.715 (7)
H16A	0.6232	1.1103	0.7185	0.120*	0.357 (3)
H16B	0.5378	1.2173	0.6555	0.120*	0.357 (3)
H16C	0.6568	1.2645	0.6877	0.120*	0.357 (3)
H16D	0.5887	1.2844	0.6560	0.120*	0.357 (3)
H16E	0.6740	1.1774	0.7190	0.120*	0.357 (3)
H16F	0.5550	1.1302	0.6868	0.120*	0.357 (3)
C16'	0.6633 (10)	0.9630 (14)	0.6786 (7)	0.076 (4)	0.285 (7)
H16G	0.6032	0.9039	0.6789	0.114*	0.285 (7)
H16H	0.6714	1.0420	0.7240	0.114*	0.285 (7)
H16I	0.7255	0.9022	0.6953	0.114*	0.285 (7)
Co1	0.5000	0.5000	0.0000	0.03909 (15)
N1	0.49372 (16)	0.7170 (2)	0.05333 (14)	0.0437 (5)
N2	0.53624 (17)	0.9358 (2)	0.11836 (14)	0.0461 (5)
N3	0.5953 (2)	1.1748 (3)	0.31929 (19)	0.0558 (6)
H3	0.575 (2)	1.262 (4)	0.294 (2)	0.073 (11)*
N4	0.6438 (2)	0.9388 (3)	0.32717 (17)	0.0583 (6)
O1	0.40498 (13)	0.4281 (2)	0.08257 (12)	0.0504 (5)
O2	0.51834 (13)	0.4364 (2)	0.22791 (12)	0.0486 (4)
O3	0.64469 (17)	0.4540 (2)	0.10984 (14)	0.0485 (5)
H3A	0.699 (3)	0.506 (4)	0.120 (3)	0.092 (13)*
H3B	0.621 (3)	0.455 (4)	0.153 (3)	0.077 (12)*
O4	0.6720 (2)	0.6225 (3)	0.3459 (2)	0.0839 (8)
H4A	0.662 (4)	0.710 (6)	0.332 (3)	0.14 (2)*
H4B	0.621 (3)	0.579 (4)	0.317 (3)	0.091 (14)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0422 (14)	0.0371 (13)	0.0450 (15)	−0.0024 (11)	0.0226 (11)	−0.0004 (11)
C2	0.0368 (13)	0.0686 (18)	0.0392 (14)	0.0046 (13)	0.0143 (11)	0.0061 (13)
C3	0.0386 (13)	0.0380 (13)	0.0403 (13)	0.0005 (10)	0.0193 (11)	0.0004 (10)
C4	0.0450 (15)	0.0604 (17)	0.0331 (13)	−0.0057 (12)	0.0188 (11)	−0.0057 (12)
C5	0.0386 (14)	0.0515 (16)	0.0490 (15)	0.0057 (12)	0.0157 (11)	−0.0018 (12)
C6	0.0353 (14)	0.077 (2)	0.0473 (16)	0.0040 (13)	0.0123 (12)	−0.0108 (14)
C7	0.0466 (16)	0.075 (2)	0.0456 (16)	0.0175 (15)	0.0144 (12)	−0.0058 (14)
C8	0.0674 (19)	0.0477 (16)	0.0476 (16)	−0.0021 (14)	0.0168 (14)	−0.0012 (13)
C9	0.0490 (15)	0.0444 (15)	0.0466 (15)	−0.0030 (12)	0.0112 (12)	−0.0035 (12)
C10	0.052 (4)	0.036 (3)	0.052 (5)	−0.009 (2)	0.013 (3)	−0.004 (2)
C10'	0.030 (7)	0.023 (9)	0.073 (12)	−0.007 (6)	0.012 (6)	0.001 (6)
C11'	0.054 (12)	0.06 (2)	0.032 (9)	−0.013 (10)	0.005 (7)	−0.002 (8)
C12'	0.059 (9)	0.041 (9)	0.049 (9)	−0.002 (7)	0.011 (6)	0.000 (7)
C13'	0.051 (8)	0.044 (12)	0.033 (6)	−0.005 (9)	0.011 (5)	−0.012 (9)
C14'	0.036 (6)	0.059 (10)	0.049 (8)	−0.007 (7)	−0.003 (5)	−0.027 (7)
C15'	0.047 (8)	0.062 (10)	0.049 (7)	−0.010 (8)	0.008 (6)	−0.025 (7)
C11	0.042 (3)	0.046 (6)	0.038 (3)	−0.017 (4)	0.008 (2)	−0.010 (3)
C12	0.045 (3)	0.060 (4)	0.070 (4)	−0.005 (3)	0.011 (3)	−0.017 (3)
C13	0.051 (4)	0.066 (6)	0.050 (3)	−0.018 (4)	0.015 (2)	−0.021 (4)
C14	0.073 (4)	0.064 (5)	0.053 (4)	−0.011 (4)	0.019 (3)	−0.001 (3)
C15	0.083 (5)	0.050 (4)	0.057 (4)	0.005 (3)	0.019 (3)	0.005 (3)
C16	0.079 (3)	0.105 (4)	0.056 (3)	−0.002 (3)	0.019 (2)	−0.021 (3)
C16'	0.083 (9)	0.087 (9)	0.047 (7)	−0.013 (7)	0.003 (6)	0.009 (6)
Co1	0.0340 (3)	0.0520 (3)	0.0358 (3)	−0.0030 (2)	0.01726 (19)	−0.0027 (2)
N1	0.0391 (11)	0.0552 (13)	0.0395 (11)	0.0006 (10)	0.0159 (9)	−0.0049 (10)
N2	0.0495 (13)	0.0511 (13)	0.0379 (11)	0.0061 (11)	0.0129 (10)	−0.0006 (10)
N3	0.0587 (15)	0.0501 (16)	0.0516 (15)	0.0057 (12)	0.0052 (12)	−0.0075 (12)
N4	0.0769 (17)	0.0472 (13)	0.0494 (14)	−0.0012 (13)	0.0164 (12)	0.0007 (11)
O1	0.0439 (10)	0.0732 (13)	0.0412 (10)	−0.0101 (9)	0.0238 (8)	−0.0053 (9)
O2	0.0372 (10)	0.0648 (12)	0.0471 (10)	0.0004 (9)	0.0174 (8)	0.0040 (9)
O3	0.0397 (11)	0.0644 (13)	0.0438 (11)	−0.0024 (10)	0.0159 (9)	−0.0023 (9)
O4	0.0580 (15)	0.0581 (16)	0.113 (2)	0.0126 (13)	−0.0099 (14)	−0.0121 (15)

Geometric parameters (Å, º)

C1—O1	1.249 (3)	C13'—C16'	1.474 (15)
C1—O2	1.261 (3)	C14'—C15'	1.3900
C1—C3	1.504 (3)	C14'—H14'	0.9300
C2—C3	1.382 (3)	C15'—H15'	0.9300
C2—C4^i	1.384 (3)	C11—C12	1.401 (7)
C2—H2	0.9300	C11—N3	1.438 (6)
C3—C4	1.383 (3)	C12—C13	1.381 (9)
C4—C2^i	1.384 (3)	C12—H12	0.9300
C4—H4	0.9300	C13—C14	1.383 (9)
C5—N1	1.310 (3)	C13—C16	1.543 (8)
C5—N2	1.340 (3)	C14—C15	1.349 (9)
C5—H5	0.9300	C14—H14	0.9300
C6—C7	1.345 (4)	C15—H15	0.9300
C6—N1	1.369 (3)	C16—H16A	0.9600
C6—H6	0.9300	C16—H16B	0.9600
C7—N2	1.363 (3)	C16—H16C	0.9600
C7—H7	0.9300	C16—H16D	0.9600
C8—N2	1.458 (3)	C16—H16E	0.9600
C8—C9	1.492 (4)	C16—H16F	0.9600
C8—H8A	0.9700	C16'—H16G	0.9600
C8—H8B	0.9700	C16'—H16H	0.9600
C9—N4	1.304 (3)	C16'—H16I	0.9600
C9—N3	1.349 (3)	Co1—O1^ii	2.093 (2)
C10—N4	1.367 (7)	Co1—O1	2.093 (2)
C10—C11	1.373 (9)	Co1—N1	2.119 (2)
C10—C15	1.391 (9)	Co1—N1^ii	2.119 (2)
C10'—N3	1.258 (10)	Co1—O3	2.156 (2)
C10'—C11'	1.3900	Co1—O3^ii	2.156 (2)
C10'—C15'	1.3900	N3—H3	0.88 (3)
C11'—C12'	1.3900	O3—H3A	0.83 (4)
C11'—N4	1.500 (9)	O3—H3B	0.79 (4)
C12'—C13'	1.3900	O4—H4A	0.82 (5)
C12'—H12'	0.9300	O4—H4B	0.79 (4)
C13'—C14'	1.3900
O1—C1—O2	124.8 (2)	C14—C15—C10	116.6 (8)
O1—C1—C3	117.0 (2)	C14—C15—H15	121.7
O2—C1—C3	118.1 (2)	C10—C15—H15	121.7
C3—C2—C4^i	121.0 (2)	C13—C16—H16A	109.5
C3—C2—H2	119.5	C13—C16—H16B	109.5
C4^i—C2—H2	119.5	H16A—C16—H16B	109.5
C2—C3—C4	118.8 (2)	C13—C16—H16C	109.5
C2—C3—C1	120.9 (2)	H16A—C16—H16C	109.5
C4—C3—C1	120.3 (2)	H16B—C16—H16C	109.5
C3—C4—C2^i	120.2 (2)	C13—C16—H16D	109.5
C3—C4—H4	119.9	H16A—C16—H16D	141.1
C2^i—C4—H4	119.9	H16B—C16—H16D	56.3
N1—C5—N2	111.7 (2)	H16C—C16—H16D	56.3
N1—C5—H5	124.1	C13—C16—H16E	109.5
N2—C5—H5	124.1	H16A—C16—H16E	56.3
C7—C6—N1	109.7 (2)	H16B—C16—H16E	141.1
C7—C6—H6	125.1	H16C—C16—H16E	56.3
N1—C6—H6	125.1	H16D—C16—H16E	109.5
C6—C7—N2	106.5 (2)	C13—C16—H16F	109.5
C6—C7—H7	126.8	H16A—C16—H16F	56.3
N2—C7—H7	126.8	H16B—C16—H16F	56.3
N2—C8—C9	111.6 (2)	H16C—C16—H16F	141.1
N2—C8—H8A	109.3	H16D—C16—H16F	109.5
C9—C8—H8A	109.3	H16E—C16—H16F	109.5
N2—C8—H8B	109.3	C13'—C16'—H16G	109.5
C9—C8—H8B	109.3	C13'—C16'—H16H	109.5
H8A—C8—H8B	108.0	H16G—C16'—H16H	109.5
N4—C9—N3	113.3 (3)	C13'—C16'—H16I	109.5
N4—C9—C8	125.4 (3)	H16G—C16'—H16I	109.5
N3—C9—C8	121.3 (3)	H16H—C16'—H16I	109.5
N4—C10—C11	108.0 (8)	O1^ii—Co1—O1	180.00
N4—C10—C15	131.0 (11)	O1^ii—Co1—N1	91.39 (8)
C11—C10—C15	120.9 (7)	O1—Co1—N1	88.61 (8)
N3—C10'—C11'	99.6 (13)	O1^ii—Co1—N1^ii	88.61 (8)
N3—C10'—C15'	138.9 (14)	O1—Co1—N1^ii	91.39 (8)
C11'—C10'—C15'	120.0	N1—Co1—N1^ii	180.00
C12'—C11'—C10'	120.0	O1^ii—Co1—O3	86.52 (8)
C12'—C11'—N4	126.4 (13)	O1—Co1—O3	93.48 (8)
C10'—C11'—N4	113.6 (13)	N1—Co1—O3	91.32 (8)
C11'—C12'—C13'	120.0	N1^ii—Co1—O3	88.68 (8)
C11'—C12'—H12'	120.0	O1^ii—Co1—O3^ii	93.48 (8)
C13'—C12'—H12'	120.0	O1—Co1—O3^ii	86.52 (8)
C14'—C13'—C12'	120.0	N1—Co1—O3^ii	88.68 (8)
C14'—C13'—C16'	116.2 (11)	N1^ii—Co1—O3^ii	91.32 (8)
C12'—C13'—C16'	123.8 (11)	O3—Co1—O3^ii	180.00
C13'—C14'—C15'	120.0	C5—N1—C6	105.3 (2)
C13'—C14'—H14'	120.0	C5—N1—Co1	129.06 (17)
C15'—C14'—H14'	120.0	C6—N1—Co1	125.61 (18)
C14'—C15'—C10'	120.0	C5—N2—C7	106.8 (2)
C14'—C15'—H15'	120.0	C5—N2—C8	126.6 (2)
C10'—C15'—H15'	120.0	C7—N2—C8	126.5 (2)
C10—C11—C12	122.2 (6)	C10'—N3—C9	115.8 (9)
C10—C11—N3	106.9 (7)	C9—N3—C11	103.7 (5)
C12—C11—N3	130.9 (9)	C10'—N3—H3	118 (2)
C13—C12—C11	115.9 (6)	C9—N3—H3	126 (2)
C13—C12—H12	122.0	C11—N3—H3	131 (2)
C11—C12—H12	122.0	C9—N4—C10	107.9 (6)
C12—C13—C14	120.7 (7)	C9—N4—C11'	96.5 (8)
C12—C13—C16	118.4 (7)	C1—O1—Co1	127.24 (16)
C14—C13—C16	120.8 (7)	Co1—O3—H3A	124 (3)
C15—C14—C13	123.6 (8)	Co1—O3—H3B	97 (3)
C15—C14—H14	118.2	H3A—O3—H3B	112 (3)
C13—C14—H14	118.2	H4A—O4—H4B	107 (4)
C4^i—C2—C3—C4	0.1 (4)	C16—C13—C14—C15	178.7 (8)
C4^i—C2—C3—C1	179.0 (2)	C13—C14—C15—C10	−1.7 (11)
O1—C1—C3—C2	178.3 (2)	N4—C10—C15—C14	−176.1 (12)
O2—C1—C3—C2	−1.3 (4)	C11—C10—C15—C14	2.1 (9)
O1—C1—C3—C4	−2.8 (4)	N2—C5—N1—C6	−0.1 (3)
O2—C1—C3—C4	177.5 (2)	N2—C5—N1—Co1	−178.81 (16)
C2—C3—C4—C2^i	−0.7 (3)	C7—C6—N1—C5	−0.2 (3)
C1—C3—C4—C2^i	−179.5 (2)	C7—C6—N1—Co1	178.60 (18)
N1—C6—C7—N2	0.4 (3)	N1—C5—N2—C7	0.3 (3)
N2—C8—C9—N4	50.8 (4)	N1—C5—N2—C8	176.0 (2)
N2—C8—C9—N3	−130.3 (3)	C6—C7—N2—C5	−0.4 (3)
N3—C10'—C11'—C12'	−168.7 (17)	C6—C7—N2—C8	−176.1 (2)
C15'—C10'—C11'—C12'	0.0	C9—C8—N2—C5	−99.0 (3)
N3—C10'—C11'—N4	10.3 (12)	C9—C8—N2—C7	75.8 (3)
C15'—C10'—C11'—N4	179.0 (18)	C11'—C10'—N3—C9	−10.4 (11)
C10'—C11'—C12'—C13'	0.0	C15'—C10'—N3—C9	−175.4 (16)
N4—C11'—C12'—C13'	−179 (2)	N4—C9—N3—C10'	7.3 (12)
C11'—C12'—C13'—C14'	0.0	C8—C9—N3—C10'	−171.8 (11)
C11'—C12'—C13'—C16'	−178.5 (15)	N4—C9—N3—C11	−3.1 (5)
C12'—C13'—C14'—C15'	0.0	C8—C9—N3—C11	177.9 (5)
C16'—C13'—C14'—C15'	178.6 (14)	C10—C11—N3—C9	3.5 (6)
C13'—C14'—C15'—C10'	0.0	C12—C11—N3—C9	−176.6 (7)
N3—C10'—C15'—C14'	163 (2)	N3—C9—N4—C10	1.5 (6)
C11'—C10'—C15'—C14'	0.0	C8—C9—N4—C10	−179.5 (6)
N4—C10—C11—C12	177.3 (8)	N3—C9—N4—C11'	0.0 (10)
C15—C10—C11—C12	−1.3 (9)	C8—C9—N4—C11'	179.0 (10)
N4—C10—C11—N3	−2.8 (8)	C11—C10—N4—C9	0.9 (8)
C15—C10—C11—N3	178.6 (8)	C15—C10—N4—C9	179.3 (8)
C10—C11—C12—C13	0.0 (9)	C12'—C11'—N4—C9	172.4 (12)
N3—C11—C12—C13	−179.9 (8)	C10'—C11'—N4—C9	−6.5 (12)
C11—C12—C13—C14	0.5 (10)	O2—C1—O1—Co1	−23.1 (4)
C11—C12—C13—C16	−177.9 (6)	C3—C1—O1—Co1	157.31 (17)
C12—C13—C14—C15	0.4 (12)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4A···N4	0.82 (5)	2.07 (5)	2.879 (4)	168 (5)
O4—H4B···O2	0.79 (4)	2.05 (4)	2.812 (4)	164 (4)
O3—H3B···O2	0.79 (4)	2.00 (4)	2.749 (3)	160 (3)
O3—H3A···O4^iii	0.83 (4)	1.95 (4)	2.778 (3)	176 (4)
N3—H3···O2^iv	0.88 (3)	1.88 (3)	2.759 (3)	173 (3)

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

catena-Poly[[[diaquabis{2-[(1H-imidazol-1-yl)methyl]-6-methyl-1H-benzimidazole-κN³}nickel(II)]-µ₂-benzene-1,4-dicarboxylato-κ²O¹:O⁴] dihydrate] (II)

Crystal data

[Ni(C8H4O4)(C12H11N4)2(H2O)2]·2H2O	F(000) = 752
Mr = 719.40	Dx = 1.430 Mg m^−3
Monoclinic, P2/n	Mo Kα radiation, λ = 0.71073 Å
a = 13.192 (3) Å	Cell parameters from 4855 reflections
b = 9.0180 (18) Å	θ = 1.8–27.9°
c = 14.670 (3) Å	µ = 0.64 mm^−1
β = 106.84 (3)°	T = 293 K
V = 1670.3 (6) Å^3	Prism, green
Z = 2	0.22 × 0.19 × 0.15 mm

Data collection

Rigaku Saturn diffractometer	3181 independent reflections
Radiation source: fine-focus sealed tube	2903 reflections with I > 2σ(I)
Detector resolution: 28.5714 pixels mm^-1	Rint = 0.033
ω scans	θmax = 25.8°, θmin = 2.3°
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2004)	h = −16→16
Tmin = 0.872, Tmax = 0.910	k = −10→11
15587 measured reflections	l = −17→17

Refinement

Refinement on F^2	36 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.090	w = 1/[σ^2(Fo^2) + (0.0406P)^2 + 0.5458P] where P = (Fo^2 + 2Fc^2)/3
S = 1.11	(Δ/σ)max < 0.001
3181 reflections	Δρmax = 0.22 e Å^−3
297 parameters	Δρmin = −0.18 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.42695 (16)	0.4313 (2)	0.17018 (14)	0.0367 (4)
C2	0.35197 (17)	0.4283 (3)	0.30946 (14)	0.0471 (5)
H2	0.4208	0.4277	0.3500	0.056*
C3	0.33531 (15)	0.4285 (2)	0.21193 (13)	0.0358 (4)
C4	0.23241 (16)	0.4290 (3)	0.15263 (14)	0.0451 (5)
H4	0.2200	0.4298	0.0869	0.054*
C5	0.57167 (16)	0.8043 (2)	0.08937 (14)	0.0441 (5)
H5	0.6426	0.7847	0.0957	0.053*
C6	0.40373 (16)	0.7832 (3)	0.05705 (15)	0.0510 (6)
H6	0.3356	0.7443	0.0360	0.061*
C7	0.42872 (18)	0.9174 (3)	0.09633 (16)	0.0547 (6)
H7	0.3821	0.9876	0.1074	0.066*
C8	0.6002 (2)	1.0549 (3)	0.16573 (16)	0.0539 (6)
H8A	0.5667	1.1473	0.1393	0.065*
H8B	0.6693	1.0508	0.1551	0.065*
C9	0.61322 (18)	1.0516 (2)	0.27010 (16)	0.0472 (5)
C10	0.6444 (8)	0.9759 (11)	0.4161 (5)	0.0492 (18)	0.697 (6)
C10'	0.6197 (14)	1.1621 (15)	0.4064 (6)	0.037 (4)	0.303 (6)
C11'	0.6390 (15)	1.0106 (15)	0.4167 (7)	0.038 (4)	0.303 (6)
C12'	0.6522 (13)	0.9433 (11)	0.5046 (9)	0.047 (4)	0.303 (6)
H12'	0.6651	0.8420	0.5115	0.057*	0.303 (6)
C13'	0.6462 (11)	1.0275 (12)	0.5822 (6)	0.051 (5)	0.303 (6)
C14'	0.6268 (12)	1.1790 (11)	0.5719 (7)	0.060 (5)	0.303 (6)
H14'	0.6228	1.2354	0.6238	0.072*	0.303 (6)
C15'	0.6136 (13)	1.2463 (10)	0.4840 (9)	0.051 (4)	0.303 (6)
H15'	0.6007	1.3477	0.4771	0.061*	0.303 (6)
C11	0.6128 (7)	1.1220 (10)	0.4135 (4)	0.0438 (16)	0.697 (6)
C12	0.6020 (7)	1.1966 (7)	0.4939 (5)	0.0593 (15)	0.697 (6)
H12	0.5809	1.2953	0.4913	0.071*	0.697 (6)
C13	0.6244 (6)	1.1160 (8)	0.5766 (4)	0.0576 (17)	0.697 (6)
C14	0.6569 (8)	0.9697 (9)	0.5778 (5)	0.0617 (17)	0.697 (6)
H14	0.6713	0.9184	0.6351	0.074*	0.697 (6)
C15	0.6690 (7)	0.8968 (8)	0.5011 (5)	0.0611 (16)	0.697 (6)
H15	0.6925	0.7992	0.5050	0.073*	0.697 (6)
C16	0.6097 (3)	1.1880 (6)	0.6665 (3)	0.0814 (15)	0.697 (6)
H16A	0.6726	1.2420	0.6988	0.122*	0.697 (6)
H16B	0.5969	1.1125	0.7079	0.122*	0.697 (6)
H16C	0.5506	1.2548	0.6492	0.122*	0.697 (6)
C16'	0.6640 (8)	0.9652 (12)	0.6789 (6)	0.073 (3)	0.303 (6)
H16D	0.6017	0.9131	0.6822	0.109*	0.303 (6)
H16E	0.6791	1.0441	0.7248	0.109*	0.303 (6)
H16F	0.7229	0.8979	0.6924	0.109*	0.303 (6)
N1	0.49428 (13)	0.7118 (2)	0.05257 (11)	0.0420 (4)
N2	0.53602 (14)	0.9308 (2)	0.11685 (12)	0.0452 (4)
N3	0.59670 (16)	1.1736 (2)	0.31720 (14)	0.0536 (5)
H3	0.5757 (19)	1.263 (3)	0.2889 (18)	0.064 (8)*
N4	0.64210 (17)	0.9366 (2)	0.32602 (14)	0.0565 (5)
Ni1	0.5000	0.5000	0.0000	0.03690 (13)
O1	0.40555 (11)	0.42918 (18)	0.08146 (10)	0.0467 (4)
O2	0.51951 (11)	0.43598 (18)	0.22723 (10)	0.0460 (4)
O3	0.64197 (13)	0.4527 (2)	0.10704 (11)	0.0452 (4)
H3A	0.693 (3)	0.509 (3)	0.114 (2)	0.076 (10)*
H3B	0.623 (2)	0.458 (3)	0.152 (2)	0.073 (10)*
O4	0.67274 (18)	0.6210 (3)	0.34811 (18)	0.0803 (7)
H4A	0.662 (3)	0.698 (4)	0.331 (3)	0.100 (14)*
H4B	0.620 (3)	0.573 (4)	0.317 (2)	0.081 (10)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0398 (11)	0.0363 (10)	0.0401 (11)	−0.0014 (9)	0.0210 (9)	−0.0003 (8)
C2	0.0355 (11)	0.0709 (15)	0.0374 (11)	0.0059 (10)	0.0147 (9)	0.0067 (10)
C3	0.0374 (10)	0.0361 (10)	0.0396 (10)	−0.0004 (8)	0.0201 (8)	0.0006 (8)
C4	0.0443 (12)	0.0619 (14)	0.0343 (10)	−0.0071 (10)	0.0198 (9)	−0.0070 (9)
C5	0.0376 (11)	0.0513 (13)	0.0446 (11)	0.0055 (10)	0.0138 (9)	0.0003 (9)
C6	0.0316 (11)	0.0744 (16)	0.0470 (12)	0.0054 (10)	0.0116 (9)	−0.0095 (11)
C7	0.0463 (13)	0.0697 (16)	0.0483 (13)	0.0175 (12)	0.0144 (10)	−0.0057 (12)
C8	0.0671 (16)	0.0484 (12)	0.0464 (13)	−0.0013 (12)	0.0166 (11)	−0.0001 (10)
C9	0.0483 (13)	0.0431 (11)	0.0483 (12)	−0.0011 (10)	0.0111 (10)	−0.0033 (10)
C10	0.049 (3)	0.041 (3)	0.056 (4)	−0.005 (2)	0.014 (2)	−0.003 (2)
C10'	0.028 (5)	0.022 (6)	0.059 (7)	−0.008 (4)	0.009 (4)	0.001 (4)
C11'	0.050 (7)	0.032 (9)	0.024 (5)	−0.008 (6)	0.001 (4)	0.005 (4)
C12'	0.050 (6)	0.036 (7)	0.049 (7)	0.008 (5)	0.003 (4)	0.006 (5)
C13'	0.046 (7)	0.068 (13)	0.038 (5)	−0.004 (9)	0.011 (4)	−0.024 (8)
C14'	0.044 (6)	0.068 (10)	0.056 (7)	0.003 (6)	−0.002 (4)	−0.032 (7)
C15'	0.040 (5)	0.065 (8)	0.043 (5)	−0.009 (6)	0.005 (4)	−0.022 (5)
C11	0.045 (3)	0.044 (4)	0.041 (2)	−0.013 (3)	0.0094 (19)	−0.005 (2)
C12	0.052 (3)	0.056 (3)	0.068 (4)	−0.003 (3)	0.014 (2)	−0.015 (3)
C13	0.049 (3)	0.073 (6)	0.051 (3)	−0.015 (4)	0.015 (2)	−0.026 (3)
C14	0.068 (3)	0.073 (5)	0.046 (3)	−0.010 (4)	0.018 (2)	−0.003 (3)
C15	0.083 (4)	0.047 (3)	0.054 (3)	0.004 (3)	0.021 (2)	0.008 (2)
C16	0.081 (3)	0.107 (4)	0.056 (2)	−0.002 (3)	0.019 (2)	−0.022 (2)
C16'	0.084 (7)	0.088 (7)	0.044 (5)	−0.011 (5)	0.015 (4)	0.003 (4)
N1	0.0364 (9)	0.0532 (10)	0.0392 (9)	0.0000 (8)	0.0153 (7)	−0.0040 (8)
N2	0.0466 (10)	0.0497 (10)	0.0390 (9)	0.0056 (8)	0.0120 (8)	−0.0001 (8)
N3	0.0547 (12)	0.0481 (12)	0.0523 (12)	0.0050 (10)	0.0063 (9)	−0.0064 (9)
N4	0.0740 (14)	0.0457 (11)	0.0496 (11)	−0.0002 (10)	0.0178 (10)	0.0004 (9)
Ni1	0.0313 (2)	0.0507 (2)	0.0333 (2)	−0.00215 (15)	0.01672 (15)	−0.00210 (15)
O1	0.0396 (8)	0.0688 (10)	0.0378 (7)	−0.0081 (7)	0.0208 (6)	−0.0033 (7)
O2	0.0352 (8)	0.0627 (9)	0.0432 (8)	−0.0001 (7)	0.0164 (6)	0.0035 (7)
O3	0.0373 (8)	0.0614 (10)	0.0392 (8)	−0.0027 (8)	0.0149 (7)	−0.0021 (7)
O4	0.0576 (13)	0.0571 (13)	0.1059 (17)	0.0115 (11)	−0.0085 (11)	−0.0106 (12)

Geometric parameters (Å, º)

C1—O1	1.249 (2)	C12'—H12'	0.9300
C1—O2	1.265 (2)	C13'—C14'	1.3900
C1—C3	1.505 (3)	C13'—C16'	1.480 (12)
C2—C4^i	1.381 (3)	C14'—C15'	1.3900
C2—C3	1.383 (3)	C14'—H14'	0.9300
C2—H2	0.9300	C15'—H15'	0.9300
C3—C4	1.384 (3)	C11—C12	1.400 (6)
C4—C2^i	1.381 (3)	C11—N3	1.444 (6)
C4—H4	0.9300	C12—C13	1.371 (9)
C5—N1	1.307 (3)	C12—H12	0.9300
C5—N2	1.340 (3)	C13—C14	1.385 (8)
C5—H5	0.9300	C13—C16	1.532 (7)
C6—C7	1.340 (3)	C14—C15	1.352 (8)
C6—N1	1.375 (3)	C14—H14	0.9300
C6—H6	0.9300	C15—H15	0.9300
C7—N2	1.364 (3)	C16—H16A	0.9600
C7—H7	0.9300	C16—H16B	0.9600
C8—N2	1.460 (3)	C16—H16C	0.9600
C8—C9	1.491 (3)	C16'—H16D	0.9600
C8—H8A	0.9700	C16'—H16E	0.9600
C8—H8B	0.9700	C16'—H16F	0.9600
C9—N4	1.309 (3)	N3—H3	0.91 (3)
C9—N3	1.350 (3)	Ni1—O1^ii	2.0618 (14)
C10—N4	1.360 (7)	Ni1—O1	2.0618 (14)
C10—C11	1.379 (7)	Ni1—N1	2.0696 (18)
C10—C15	1.391 (7)	Ni1—N1^ii	2.0697 (18)
C10'—N3	1.259 (8)	Ni1—O3	2.1097 (17)
C10'—C11'	1.3900	Ni1—O3^ii	2.1097 (17)
C10'—C15'	1.3900	O3—H3A	0.83 (3)
C11'—C12'	1.3900	O3—H3B	0.76 (3)
C11'—N4	1.499 (8)	O4—H4A	0.74 (4)
C12'—C13'	1.3900	O4—H4B	0.84 (3)
O1—C1—O2	124.96 (17)	C11—C12—H12	121.9
O1—C1—C3	117.25 (18)	C12—C13—C14	120.2 (6)
O2—C1—C3	117.79 (17)	C12—C13—C16	119.3 (6)
C4^i—C2—C3	120.76 (19)	C14—C13—C16	120.6 (6)
C4^i—C2—H2	119.6	C15—C14—C13	124.3 (7)
C3—C2—H2	119.6	C15—C14—H14	117.9
C2—C3—C4	118.90 (18)	C13—C14—H14	117.9
C2—C3—C1	121.01 (18)	C14—C15—C10	116.3 (6)
C4—C3—C1	120.08 (17)	C14—C15—H15	121.8
C2^i—C4—C3	120.33 (19)	C10—C15—H15	121.8
C2^i—C4—H4	119.8	C13—C16—H16A	109.5
C3—C4—H4	119.8	C13—C16—H16B	109.5
N1—C5—N2	111.54 (18)	H16A—C16—H16B	109.5
N1—C5—H5	124.2	C13—C16—H16C	109.5
N2—C5—H5	124.2	H16A—C16—H16C	109.5
C7—C6—N1	109.5 (2)	H16B—C16—H16C	109.5
C7—C6—H6	125.2	C13'—C16'—H16D	109.5
N1—C6—H6	125.2	C13'—C16'—H16E	109.5
C6—C7—N2	106.6 (2)	H16D—C16'—H16E	109.5
C6—C7—H7	126.7	C13'—C16'—H16F	109.5
N2—C7—H7	126.7	H16D—C16'—H16F	109.5
N2—C8—C9	111.57 (19)	H16E—C16'—H16F	109.5
N2—C8—H8A	109.3	C5—N1—C6	105.49 (18)
C9—C8—H8A	109.3	C5—N1—Ni1	129.35 (14)
N2—C8—H8B	109.3	C6—N1—Ni1	125.15 (15)
C9—C8—H8B	109.3	C5—N2—C7	106.86 (19)
H8A—C8—H8B	108.0	C5—N2—C8	126.61 (19)
N4—C9—N3	112.7 (2)	C7—N2—C8	126.4 (2)
N4—C9—C8	125.8 (2)	C10'—N3—C9	116.1 (7)
N3—C9—C8	121.5 (2)	C9—N3—C11	103.8 (4)
N4—C10—C11	107.5 (6)	C10'—N3—H3	119.6 (17)
N4—C10—C15	132.2 (8)	C9—N3—H3	124.1 (16)
C11—C10—C15	120.3 (6)	C11—N3—H3	132.0 (16)
N3—C10'—C11'	100.1 (10)	C9—N4—C10	108.8 (4)
N3—C10'—C15'	138.8 (10)	C9—N4—C11'	97.2 (6)
C11'—C10'—C15'	120.0	O1^ii—Ni1—O1	180.00
C12'—C11'—C10'	120.0	O1^ii—Ni1—N1	91.34 (6)
C12'—C11'—N4	126.9 (9)	O1—Ni1—N1	88.66 (6)
C10'—C11'—N4	113.1 (9)	O1^ii—Ni1—N1^ii	88.66 (6)
C11'—C12'—C13'	120.0	O1—Ni1—N1^ii	91.34 (6)
C11'—C12'—H12'	120.0	N1—Ni1—N1^ii	180.00
C13'—C12'—H12'	120.0	O1^ii—Ni1—O3	86.49 (7)
C14'—C13'—C12'	120.0	O1—Ni1—O3	93.51 (7)
C14'—C13'—C16'	116.8 (9)	N1—Ni1—O3	91.69 (7)
C12'—C13'—C16'	123.1 (9)	N1^ii—Ni1—O3	88.31 (7)
C13'—C14'—C15'	120.0	O1^ii—Ni1—O3^ii	93.51 (6)
C13'—C14'—H14'	120.0	O1—Ni1—O3^ii	86.49 (7)
C15'—C14'—H14'	120.0	N1—Ni1—O3^ii	88.31 (7)
C14'—C15'—C10'	120.0	N1^ii—Ni1—O3^ii	91.69 (7)
C14'—C15'—H15'	120.0	O3^ii—Ni1—O3	180.00
C10'—C15'—H15'	120.0	C1—O1—Ni1	127.37 (13)
C10—C11—C12	122.6 (5)	Ni1—O3—H3A	119 (2)
C10—C11—N3	107.0 (6)	Ni1—O3—H3B	101 (2)
C12—C11—N3	130.3 (7)	H3A—O3—H3B	108 (3)
C13—C12—C11	116.2 (6)	H4A—O4—H4B	105 (3)
C13—C12—H12	121.9
C4^i—C2—C3—C4	−0.2 (3)	C16—C13—C14—C15	178.2 (7)
C4^i—C2—C3—C1	178.6 (2)	C13—C14—C15—C10	−1.4 (10)
O1—C1—C3—C2	179.0 (2)	N4—C10—C15—C14	−176.2 (11)
O2—C1—C3—C2	−1.2 (3)	C11—C10—C15—C14	2.0 (7)
O1—C1—C3—C4	−2.2 (3)	N2—C5—N1—C6	−0.2 (2)
O2—C1—C3—C4	177.55 (19)	N2—C5—N1—Ni1	−178.96 (13)
C2—C3—C4—C2^i	−0.4 (3)	C7—C6—N1—C5	0.1 (2)
C1—C3—C4—C2^i	−179.2 (2)	C7—C6—N1—Ni1	178.95 (15)
N1—C6—C7—N2	0.0 (3)	N1—C5—N2—C7	0.2 (2)
N2—C8—C9—N4	49.2 (3)	N1—C5—N2—C8	176.11 (18)
N2—C8—C9—N3	−131.7 (2)	C6—C7—N2—C5	−0.1 (2)
N3—C10'—C11'—C12'	−170.3 (13)	C6—C7—N2—C8	−176.0 (2)
C15'—C10'—C11'—C12'	0.0	C9—C8—N2—C5	−99.8 (3)
N3—C10'—C11'—N4	9.2 (9)	C9—C8—N2—C7	75.3 (3)
C15'—C10'—C11'—N4	179.5 (14)	C11'—C10'—N3—C9	−8.9 (9)
C10'—C11'—C12'—C13'	0.0	C15'—C10'—N3—C9	−176.1 (12)
N4—C11'—C12'—C13'	−179.4 (16)	N4—C9—N3—C10'	5.8 (9)
C11'—C12'—C13'—C14'	0.0	C8—C9—N3—C10'	−173.5 (9)
C11'—C12'—C13'—C16'	−177.2 (13)	N4—C9—N3—C11	−3.2 (4)
C12'—C13'—C14'—C15'	0.0	C8—C9—N3—C11	177.6 (4)
C16'—C13'—C14'—C15'	177.4 (12)	C10—C11—N3—C9	3.9 (5)
C13'—C14'—C15'—C10'	0.0	C12—C11—N3—C9	−176.8 (6)
N3—C10'—C15'—C14'	165.4 (19)	N3—C9—N4—C10	1.3 (5)
C11'—C10'—C15'—C14'	0.0	C8—C9—N4—C10	−179.5 (5)
N4—C10—C11—C12	177.4 (7)	N3—C9—N4—C11'	0.6 (8)
C15—C10—C11—C12	−1.2 (7)	C8—C9—N4—C11'	179.8 (8)
N4—C10—C11—N3	−3.2 (7)	C11—C10—N4—C9	1.3 (7)
C15—C10—C11—N3	178.2 (7)	C15—C10—N4—C9	179.7 (7)
C10—C11—C12—C13	−0.2 (7)	C12'—C11'—N4—C9	173.3 (10)
N3—C11—C12—C13	−179.4 (8)	C10'—C11'—N4—C9	−6.2 (9)
C11—C12—C13—C14	0.8 (9)	O2—C1—O1—Ni1	−21.9 (3)
C11—C12—C13—C16	−177.4 (6)	C3—C1—O1—Ni1	157.87 (13)
C12—C13—C14—C15	0.1 (12)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4A···N4	0.74 (4)	2.16 (4)	2.880 (3)	163 (4)
O4—H4B···O2	0.84 (3)	2.00 (3)	2.817 (3)	166 (3)
O3—H3B···O2	0.76 (3)	2.01 (3)	2.719 (2)	155 (3)
O3—H3A···O4^iii	0.83 (3)	1.97 (3)	2.789 (3)	169 (3)
N3—H3···O2^iv	0.91 (3)	1.85 (3)	2.757 (3)	174 (2)

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