A one-dimensional zinc(II) coordination polymer based on mixed multidentate N- and O-donor ligands

In the title coordination polymer, catena-poly[[bis­[{1-[(1H-benzimidazol-2-yl-[kappa]N³)meth­yl]-1H-tetra­zole}zinc(II)]-bis­([mu]₄-pentane-1,5-dioato-1:2:1':2'[kappa]⁴O¹:O^1':O⁵:O^5')] methanol disolvate], {[Zn(C₅H₆O₄)(C₉H₈N₆)]·CH₃OH}_n, each Zn^II ion is five-coordinated by four O atoms from four glutarate ligands and by one N atom from a 1-[(1H-benzimidazol-2-yl)meth­yl]-1H-tetra­zole (bimt) ligand, leading to a slightly distorted square-pyramidal coordination environment. Two Zn^II ions are linked by four bridging glutarate carboxyl­ate groups to generate a dinuclear [Zn₂(CO₂)₄] paddle-wheel unit. The dinuclear units are further connected into a one-dimensional chain via the glutarate ligands. The bimt ligands coordinate to the Zn^II ions in a monodentate mode and are pendant on both sides of the main chain. In the crystal, the chains are linked by O-H...O and N-H...O hydrogen bonds into a two-dimensional layered structure. Adjacent layers are further packed into a three-dimensional network through van der Waals forces. A thermogravimetric analysis was carried out and the photoluminescent behaviour of the polymer was investigated.

Computing details

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[[bis({1-[(1H-benzoimidazol-2-yl-κN³)methyl]-1H-tetrazole}zinc(II))-bis(µ₄-pentane-1,5-dioato-1:2:1':2'κ⁴O¹:O^1':O⁵:O^5')] methanol disolvate]

Crystal data

[Zn(C5H6O4)(C9H8N6)]·CH4O	Z = 2
Mr = 427.72	F(000) = 440
Triclinic, P1	Dx = 1.670 Mg m^−3
a = 8.0054 (16) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.972 (2) Å	Cell parameters from 3051 reflections
c = 11.451 (2) Å	θ = 1.9–27.8°
α = 80.91 (3)°	µ = 1.49 mm^−1
β = 71.17 (3)°	T = 293 K
γ = 81.95 (3)°	Prism, colourless
V = 850.4 (3) Å^3	0.19 × 0.16 × 0.14 mm

Data collection

Rigaku Saturn diffractometer	4009 independent reflections
Radiation source: fine-focus sealed tube	3705 reflections with I > 2σ(I)
Detector resolution: 28.5714 pixels mm^-1	Rint = 0.025
ω scans	θmax = 27.8°, θmin = 1.9°
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2004)	h = −10→10
Tmin = 0.765, Tmax = 0.819	k = −13→13
9586 measured reflections	l = −14→15

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.034	H-atom parameters constrained
wR(F^2) = 0.077	w = 1/[σ^2(Fo^2) + (0.0313P)^2 + 0.541P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
4009 reflections	Δρmax = 0.37 e Å^−3
246 parameters	Δρmin = −0.29 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.

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

	x	y	z	Uiso*/Ueq
Zn1	0.46423 (3)	0.50463 (2)	0.13821 (2)	0.02204 (8)
N1	0.3901 (2)	0.51814 (16)	0.32362 (15)	0.0217 (3)
N2	0.3065 (2)	0.60860 (17)	0.50073 (16)	0.0260 (4)
H2C	0.2981	0.6647	0.5526	0.031*
N3	0.4175 (2)	0.85403 (17)	0.26797 (16)	0.0265 (4)
N4	0.2742 (3)	0.9239 (2)	0.3382 (2)	0.0423 (5)
N5	0.2268 (3)	1.0222 (2)	0.2634 (2)	0.0483 (6)
N6	0.3377 (3)	1.0192 (2)	0.1458 (2)	0.0437 (5)
O1	0.2652 (2)	0.40809 (18)	0.12769 (15)	0.0361 (4)
O2	0.3140 (2)	0.39357 (17)	−0.07241 (15)	0.0348 (4)
O3	−0.3248 (2)	0.31979 (16)	−0.08042 (15)	0.0370 (4)
O4	−0.3719 (2)	0.32404 (16)	0.12162 (14)	0.0326 (3)
C1	0.2257 (3)	0.3736 (2)	0.04071 (19)	0.0240 (4)
C2	0.0546 (3)	0.3075 (2)	0.0752 (2)	0.0266 (4)
H2A	−0.0436	0.3780	0.0931	0.032*
H2B	0.0445	0.2455	0.1509	0.032*
C3	0.0361 (3)	0.2293 (2)	−0.0225 (2)	0.0298 (5)
H3A	0.1321	0.1570	−0.0390	0.036*
H3B	0.0481	0.2905	−0.0990	0.036*
C4	−0.1417 (3)	0.1663 (2)	0.0150 (2)	0.0279 (4)
H4A	−0.1373	0.1055	−0.0444	0.033*
H4B	−0.1616	0.1133	0.0961	0.033*
C5	−0.2932 (3)	0.2774 (2)	0.0189 (2)	0.0250 (4)
C6	0.2791 (3)	0.4319 (2)	0.41569 (18)	0.0228 (4)
C7	0.2209 (3)	0.3089 (2)	0.4096 (2)	0.0295 (5)
H7A	0.2568	0.2691	0.3362	0.035*
C8	0.1079 (3)	0.2487 (2)	0.5171 (2)	0.0343 (5)
H8A	0.0684	0.1655	0.5164	0.041*
C9	0.0508 (3)	0.3089 (2)	0.6275 (2)	0.0348 (5)
H9A	−0.0274	0.2657	0.6977	0.042*
C10	0.1073 (3)	0.4304 (2)	0.6348 (2)	0.0319 (5)
H10A	0.0692	0.4708	0.7080	0.038*
C11	0.2245 (3)	0.4898 (2)	0.52685 (18)	0.0241 (4)
C12	0.4017 (3)	0.6211 (2)	0.37993 (18)	0.0225 (4)
C13	0.5125 (3)	0.7375 (2)	0.3217 (2)	0.0276 (4)
H13A	0.5527	0.7668	0.3841	0.033*
H13B	0.6165	0.7062	0.2570	0.033*
C14	0.4531 (3)	0.9143 (2)	0.1516 (2)	0.0354 (5)
H14A	0.5461	0.8859	0.0845	0.043*
O5	−0.3134 (3)	0.21542 (18)	0.34153 (18)	0.0505 (5)
H5	−0.3365	0.2417	0.2764	0.076*
C15	−0.2966 (7)	0.0757 (3)	0.3595 (3)	0.0861 (13)
H15A	−0.2874	0.0450	0.4412	0.129*
H15B	−0.1920	0.0418	0.2985	0.129*
H15C	−0.3988	0.0424	0.3515	0.129*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.02097 (13)	0.02804 (13)	0.01803 (13)	−0.00364 (9)	−0.00587 (9)	−0.00454 (9)
N1	0.0241 (8)	0.0224 (8)	0.0185 (8)	−0.0032 (6)	−0.0061 (7)	−0.0027 (6)
N2	0.0337 (10)	0.0259 (9)	0.0194 (8)	−0.0011 (7)	−0.0088 (7)	−0.0061 (7)
N3	0.0296 (9)	0.0241 (9)	0.0269 (9)	−0.0043 (7)	−0.0092 (8)	−0.0036 (7)
N4	0.0444 (12)	0.0369 (11)	0.0375 (12)	0.0051 (9)	−0.0043 (10)	−0.0059 (9)
N5	0.0510 (13)	0.0368 (12)	0.0523 (14)	0.0087 (10)	−0.0149 (11)	−0.0044 (10)
N6	0.0544 (14)	0.0349 (11)	0.0416 (12)	0.0002 (10)	−0.0200 (11)	0.0030 (9)
O1	0.0310 (8)	0.0508 (10)	0.0325 (9)	−0.0148 (7)	−0.0115 (7)	−0.0087 (7)
O2	0.0287 (8)	0.0464 (10)	0.0285 (8)	−0.0162 (7)	−0.0032 (7)	−0.0035 (7)
O3	0.0435 (9)	0.0361 (9)	0.0333 (9)	0.0076 (7)	−0.0190 (8)	−0.0046 (7)
O4	0.0323 (8)	0.0334 (8)	0.0326 (9)	0.0048 (7)	−0.0115 (7)	−0.0091 (7)
C1	0.0197 (9)	0.0235 (10)	0.0293 (11)	−0.0015 (8)	−0.0085 (8)	−0.0031 (8)
C2	0.0224 (10)	0.0321 (11)	0.0264 (11)	−0.0079 (8)	−0.0064 (8)	−0.0045 (8)
C3	0.0242 (10)	0.0334 (11)	0.0334 (12)	−0.0022 (9)	−0.0086 (9)	−0.0097 (9)
C4	0.0276 (11)	0.0245 (10)	0.0349 (12)	−0.0008 (8)	−0.0133 (9)	−0.0070 (8)
C5	0.0210 (10)	0.0240 (10)	0.0322 (11)	−0.0051 (8)	−0.0094 (8)	−0.0050 (8)
C6	0.0232 (10)	0.0238 (10)	0.0205 (10)	0.0001 (8)	−0.0072 (8)	−0.0009 (7)
C7	0.0335 (12)	0.0261 (11)	0.0290 (11)	−0.0043 (9)	−0.0086 (9)	−0.0043 (8)
C8	0.0344 (12)	0.0293 (11)	0.0390 (13)	−0.0083 (9)	−0.0121 (10)	0.0028 (9)
C9	0.0292 (11)	0.0402 (13)	0.0282 (12)	−0.0060 (10)	−0.0046 (9)	0.0093 (9)
C10	0.0325 (12)	0.0391 (12)	0.0204 (10)	0.0002 (9)	−0.0051 (9)	−0.0022 (9)
C11	0.0252 (10)	0.0256 (10)	0.0214 (10)	0.0010 (8)	−0.0082 (8)	−0.0030 (8)
C12	0.0251 (10)	0.0243 (10)	0.0199 (10)	0.0005 (8)	−0.0103 (8)	−0.0027 (7)
C13	0.0304 (11)	0.0259 (10)	0.0300 (11)	−0.0053 (8)	−0.0136 (9)	−0.0025 (8)
C14	0.0429 (13)	0.0355 (12)	0.0258 (11)	−0.0044 (10)	−0.0088 (10)	−0.0008 (9)
O5	0.0822 (14)	0.0398 (10)	0.0400 (11)	0.0044 (9)	−0.0335 (10)	−0.0131 (8)
C15	0.169 (4)	0.0453 (18)	0.0456 (19)	−0.017 (2)	−0.034 (2)	−0.0013 (14)

Geometric parameters (Å, º)

Zn1—O1	2.0178 (16)	C2—H2B	0.9700
Zn1—N1	2.0328 (17)	C3—C4	1.541 (3)
Zn1—O2^i	2.0372 (16)	C3—H3A	0.9700
Zn1—O4^ii	2.0702 (16)	C3—H3B	0.9700
Zn1—O3^iii	2.0769 (17)	C4—C5	1.518 (3)
Zn1—Zn1^i	3.0433 (8)	C4—H4A	0.9700
N1—C12	1.324 (3)	C4—H4B	0.9700
N1—C6	1.401 (3)	C6—C7	1.391 (3)
N2—C12	1.342 (3)	C6—C11	1.395 (3)
N2—C11	1.380 (3)	C7—C8	1.376 (3)
N2—H2C	0.8600	C7—H7A	0.9300
N3—C14	1.330 (3)	C8—C9	1.399 (3)
N3—N4	1.344 (3)	C8—H8A	0.9300
N3—C13	1.461 (3)	C9—C10	1.374 (3)
N4—N5	1.295 (3)	C9—H9A	0.9300
N5—N6	1.355 (3)	C10—C11	1.391 (3)
N6—C14	1.303 (3)	C10—H10A	0.9300
O1—C1	1.245 (3)	C12—C13	1.497 (3)
O2—C1	1.258 (3)	C13—H13A	0.9700
O2—Zn1^i	2.0372 (16)	C13—H13B	0.9700
O3—C5	1.241 (3)	C14—H14A	0.9300
O3—Zn1^iii	2.0769 (17)	O5—C15	1.370 (4)
O4—C5	1.269 (3)	O5—H5	0.8200
O4—Zn1^iv	2.0702 (16)	C15—H15A	0.9600
C1—C2	1.513 (3)	C15—H15B	0.9600
C2—C3	1.515 (3)	C15—H15C	0.9600
C2—H2A	0.9700
O1—Zn1—N1	101.02 (7)	C5—C4—C3	110.47 (17)
O1—Zn1—O2^i	156.45 (7)	C5—C4—H4A	109.6
N1—Zn1—O2^i	102.30 (7)	C3—C4—H4A	109.6
O1—Zn1—O4^ii	89.99 (7)	C5—C4—H4B	109.6
N1—Zn1—O4^ii	102.66 (7)	C3—C4—H4B	109.6
O2^i—Zn1—O4^ii	88.11 (7)	H4A—C4—H4B	108.1
O1—Zn1—O3^iii	84.74 (7)	O3—C5—O4	125.1 (2)
N1—Zn1—O3^iii	100.07 (7)	O3—C5—C4	117.13 (19)
O2^i—Zn1—O3^iii	87.99 (7)	O4—C5—C4	117.69 (19)
O4^ii—Zn1—O3^iii	157.25 (6)	C7—C6—C11	120.66 (19)
O1—Zn1—Zn1^i	75.00 (6)	C7—C6—N1	130.69 (19)
N1—Zn1—Zn1^i	174.04 (5)	C11—C6—N1	108.64 (18)
O2^i—Zn1—Zn1^i	81.50 (5)	C8—C7—C6	117.0 (2)
O4^ii—Zn1—Zn1^i	81.93 (5)	C8—C7—H7A	121.5
O3^iii—Zn1—Zn1^i	75.33 (5)	C6—C7—H7A	121.5
C12—N1—C6	105.45 (16)	C7—C8—C9	121.9 (2)
C12—N1—Zn1	128.26 (14)	C7—C8—H8A	119.0
C6—N1—Zn1	124.86 (13)	C9—C8—H8A	119.0
C12—N2—C11	107.85 (17)	C10—C9—C8	121.6 (2)
C12—N2—H2C	126.1	C10—C9—H9A	119.2
C11—N2—H2C	126.1	C8—C9—H9A	119.2
C14—N3—N4	107.95 (19)	C9—C10—C11	116.4 (2)
C14—N3—C13	130.11 (19)	C9—C10—H10A	121.8
N4—N3—C13	121.88 (18)	C11—C10—H10A	121.8
N5—N4—N3	106.1 (2)	N2—C11—C10	132.0 (2)
N4—N5—N6	110.9 (2)	N2—C11—C6	105.65 (17)
C14—N6—N5	105.3 (2)	C10—C11—C6	122.3 (2)
C1—O1—Zn1	134.31 (15)	N1—C12—N2	112.39 (18)
C1—O2—Zn1^i	124.08 (14)	N1—C12—C13	125.88 (18)
C5—O3—Zn1^iii	132.84 (15)	N2—C12—C13	121.68 (18)
C5—O4—Zn1^iv	123.66 (14)	N3—C13—C12	113.09 (17)
O1—C1—O2	125.04 (19)	N3—C13—H13A	109.0
O1—C1—C2	116.59 (19)	C12—C13—H13A	109.0
O2—C1—C2	118.33 (18)	N3—C13—H13B	109.0
C1—C2—C3	115.39 (18)	C12—C13—H13B	109.0
C1—C2—H2A	108.4	H13A—C13—H13B	107.8
C3—C2—H2A	108.4	N6—C14—N3	109.7 (2)
C1—C2—H2B	108.4	N6—C14—H14A	125.2
C3—C2—H2B	108.4	N3—C14—H14A	125.2
H2A—C2—H2B	107.5	C15—O5—H5	109.5
C2—C3—C4	113.75 (18)	O5—C15—H15A	109.5
C2—C3—H3A	108.8	O5—C15—H15B	109.5
C4—C3—H3A	108.8	H15A—C15—H15B	109.5
C2—C3—H3B	108.8	O5—C15—H15C	109.5
C4—C3—H3B	108.8	H15A—C15—H15C	109.5
H3A—C3—H3B	107.7	H15B—C15—H15C	109.5
C14—N3—N4—N5	0.5 (3)	C6—C7—C8—C9	1.1 (3)
C13—N3—N4—N5	177.77 (19)	C7—C8—C9—C10	−1.2 (4)
N3—N4—N5—N6	−0.8 (3)	C8—C9—C10—C11	−0.2 (3)
N4—N5—N6—C14	0.8 (3)	C12—N2—C11—C10	−177.5 (2)
Zn1—O1—C1—O2	0.7 (3)	C12—N2—C11—C6	1.0 (2)
Zn1—O1—C1—C2	−176.95 (15)	C9—C10—C11—N2	−180.0 (2)
Zn1^i—O2—C1—O1	−3.0 (3)	C9—C10—C11—C6	1.7 (3)
Zn1^i—O2—C1—C2	174.58 (14)	C7—C6—C11—N2	179.50 (18)
O1—C1—C2—C3	−162.41 (19)	N1—C6—C11—N2	−1.2 (2)
O2—C1—C2—C3	19.8 (3)	C7—C6—C11—C10	−1.8 (3)
C1—C2—C3—C4	−178.70 (17)	N1—C6—C11—C10	177.50 (18)
C2—C3—C4—C5	68.8 (2)	C6—N1—C12—N2	−0.3 (2)
Zn1^iii—O3—C5—O4	14.6 (3)	Zn1—N1—C12—N2	166.41 (13)
Zn1^iii—O3—C5—C4	−161.87 (15)	C6—N1—C12—C13	177.12 (18)
Zn1^iv—O4—C5—O3	−12.3 (3)	Zn1—N1—C12—C13	−16.2 (3)
Zn1^iv—O4—C5—C4	164.14 (13)	C11—N2—C12—N1	−0.5 (2)
C3—C4—C5—O3	85.2 (2)	C11—N2—C12—C13	−178.03 (18)
C3—C4—C5—O4	−91.5 (2)	C14—N3—C13—C12	−120.3 (2)
C12—N1—C6—C7	−179.9 (2)	N4—N3—C13—C12	63.1 (3)
Zn1—N1—C6—C7	12.8 (3)	N1—C12—C13—N3	91.1 (2)
C12—N1—C6—C11	1.0 (2)	N2—C12—C13—N3	−91.7 (2)
Zn1—N1—C6—C11	−166.33 (13)	N5—N6—C14—N3	−0.4 (3)
C11—C6—C7—C8	0.3 (3)	N4—N3—C14—N6	0.0 (3)
N1—C6—C7—C8	−178.7 (2)	C13—N3—C14—N6	−177.0 (2)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···O4	0.82	1.92	2.737 (2)	172
N2—H2C···O5^v	0.86	1.87	2.727 (2)	172

Symmetry code: (v) −x, −y+1, −z+1.