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In the coordination polymer, poly[[{μ-1-[(1H-benzimidazol-2-yl)meth­yl]-1H-imidazole-κ2N:N′}(μ-5-carb­oxy­benzene-1,3-di­carboxyl­ato-κ2O1:O3)zinc(II)] di­methyl­formamide monosolvate penta­hydrate], {[Zn(C9H4O6)(C11H10N4)]·C3H7NO·5H2O}n, the ZnII ion is coordinated by two N atoms from two symmetry-related 1-[(1H-benzimidazol-2-yl)meth­yl]-1H-imidazole (bmi) ligands and two O atoms from two symmetry-related 5-carb­oxy­benzene-1,3-di­carboxyl­ate (Hbtc2−) ligands in a slightly distorted tetra­hedral geometry. The ZnII ions are bridged by Hbtc2− and bmi ligands, leading to a 4-connected two-dimensional network with the topological notation (44.62). Adjacent layers are further connected by 12 kinds of hydrogen bonds and also by π–π inter­actions, resulting in a three-dimensional supra­molecular architecture in the solid state.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229615013224/cu3078sup1.cif
Contains datablocks I, Huang

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229615013224/cu3078Isup2.hkl
Contains datablock I

CCDC reference: 1411859

Computing details top

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).

Poly[[{µ-1-[(1H-benzimidazol-2-yl)methyl]-1H-imidazole-κ2N:N'}(µ-5-carboxybenzene-1,3-dicarboxylato-κ2O1:O3)zinc(II)] dimethylformamide monosolvate pentahydrate] top
Crystal data top
[Zn(C9H4O6)(C11H10N4)]·C3H7NO·5H2OF(000) = 1320
Mr = 634.90Dx = 1.523 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 10.174 (2) ÅCell parameters from 7004 reflections
b = 20.843 (4) Åθ = 2.0–27.9°
c = 13.274 (3) ŵ = 0.96 mm1
β = 100.40 (3)°T = 293 K
V = 2768.5 (10) Å3Prism, colourless
Z = 40.20 × 0.18 × 0.15 mm
Data collection top
Rigaku Saturn
diffractometer
6614 independent reflections
Radiation source: fine-focus sealed tube5902 reflections with I > 2σ(I)
Detector resolution: 28.5714 pixels mm-1Rint = 0.048
ω scansθmax = 27.9°, θmin = 2.3°
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2004)
h = 1313
Tmin = 0.949, Tmax = 1.000k = 2727
34313 measured reflectionsl = 1717
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.060H-atom parameters constrained
wR(F2) = 0.152 w = 1/[σ2(Fo2) + (0.0763P)2 + 1.8118P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.003
6614 reflectionsΔρmax = 0.41 e Å3
373 parametersΔρmin = 0.37 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
Zn11.07235 (3)0.60660 (2)0.68989 (3)0.02833 (12)
N11.1158 (2)0.60116 (11)0.84423 (19)0.0286 (5)
N21.1473 (3)0.61848 (13)1.0112 (2)0.0355 (6)
H21.15580.63901.06820.043*
N31.0556 (3)0.74820 (12)0.9787 (2)0.0346 (6)
N41.0384 (3)0.81465 (12)1.1025 (2)0.0324 (5)
N50.4823 (3)0.13705 (17)0.4534 (3)0.0559 (8)
O10.9114 (2)0.55000 (12)0.64959 (18)0.0411 (5)
O20.8204 (2)0.62607 (12)0.72955 (19)0.0429 (6)
O30.3301 (2)0.63177 (12)0.7006 (2)0.0464 (6)
O40.2070 (2)0.54813 (11)0.64463 (17)0.0354 (5)
O50.6453 (3)0.34656 (14)0.5641 (3)0.0833 (11)
O60.4273 (3)0.35112 (12)0.5598 (3)0.0601 (7)
H60.43270.31230.55160.090*
O70.4351 (4)0.22582 (15)0.5377 (3)0.0793 (10)
O81.1509 (4)0.66041 (17)1.2043 (2)0.0782 (10)
H8A1.09620.67121.24280.117*
H8B1.22130.67971.23300.117*
O90.7054 (4)0.73851 (18)0.7731 (3)0.0890 (11)
H9A0.74130.70360.75920.133*
H9B0.65250.73830.81590.133*
O100.9151 (4)0.83381 (18)0.7832 (3)0.0928 (12)
H10A0.84020.81450.77230.139*
H10B0.91460.86260.82850.139*
O110.0622 (5)0.43012 (17)0.5722 (3)0.1145 (16)
H11A0.09810.41590.52360.172*
H11B0.10090.46580.58840.172*
O120.3806 (7)0.7541 (2)0.7612 (4)0.159 (2)
H12A0.38690.72440.71860.238*
H12B0.40420.73610.81910.238*
C10.8126 (3)0.57484 (16)0.6822 (2)0.0335 (7)
C20.3197 (3)0.57634 (15)0.6678 (2)0.0303 (6)
C30.5475 (4)0.37631 (17)0.5752 (3)0.0431 (8)
C40.6820 (3)0.53927 (15)0.6601 (2)0.0314 (6)
C50.5654 (3)0.57057 (15)0.6740 (2)0.0304 (6)
H50.57010.61280.69700.037*
C60.4425 (3)0.53979 (14)0.6541 (2)0.0294 (6)
C70.4359 (3)0.47635 (15)0.6218 (2)0.0309 (6)
H70.35410.45530.60860.037*
C80.5517 (3)0.44437 (15)0.6092 (2)0.0331 (6)
C90.6740 (3)0.47614 (16)0.6271 (2)0.0341 (7)
H90.75080.45480.61690.041*
C101.1174 (3)0.79304 (14)1.0416 (2)0.0331 (6)
H101.20430.80721.04240.040*
C110.9194 (3)0.78199 (16)1.0754 (3)0.0401 (7)
H110.84410.78751.10520.048*
C120.9295 (3)0.74102 (17)0.9994 (3)0.0434 (8)
H120.86370.71320.96700.052*
C131.1099 (4)0.71509 (16)0.8981 (3)0.0444 (8)
H13A1.19710.73270.89430.053*
H13B1.05180.72260.83270.053*
C141.1227 (3)0.64466 (15)0.9170 (2)0.0318 (6)
C151.1563 (3)0.55305 (15)1.0003 (2)0.0320 (6)
C161.1767 (3)0.50346 (16)1.0715 (3)0.0400 (7)
H161.18810.51141.14150.048*
C171.1791 (3)0.44216 (17)1.0334 (3)0.0440 (8)
H171.19380.40771.07860.053*
C181.1598 (4)0.43062 (16)0.9278 (3)0.0430 (8)
H181.16120.38850.90480.052*
C191.1388 (3)0.47969 (15)0.8570 (2)0.0364 (7)
H191.12610.47160.78700.044*
C201.1376 (3)0.54189 (14)0.8950 (2)0.0303 (6)
C210.5163 (5)0.0996 (2)0.5460 (4)0.0647 (12)
H21A0.52970.12760.60430.097*
H21B0.59680.07590.54440.097*
H21C0.44490.07020.55090.097*
C220.4857 (6)0.1059 (3)0.3560 (4)0.0800 (15)
H22A0.45510.13530.30110.120*
H22B0.42860.06890.34900.120*
H22C0.57550.09290.35340.120*
C230.4459 (5)0.1972 (2)0.4572 (4)0.0676 (12)
H23A0.42690.21990.39600.081*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.02631 (19)0.0293 (2)0.0303 (2)0.00328 (13)0.00752 (14)0.00236 (13)
N10.0296 (12)0.0287 (12)0.0285 (12)0.0023 (10)0.0079 (10)0.0008 (9)
N20.0418 (15)0.0366 (14)0.0283 (13)0.0025 (11)0.0069 (11)0.0046 (10)
N30.0412 (15)0.0290 (13)0.0346 (13)0.0026 (11)0.0098 (11)0.0047 (10)
N40.0326 (13)0.0285 (12)0.0377 (13)0.0024 (10)0.0102 (11)0.0050 (10)
N50.055 (2)0.053 (2)0.057 (2)0.0034 (16)0.0023 (16)0.0126 (16)
O10.0230 (10)0.0531 (14)0.0481 (13)0.0020 (10)0.0090 (10)0.0027 (11)
O20.0312 (12)0.0418 (13)0.0559 (15)0.0034 (10)0.0086 (11)0.0001 (11)
O30.0379 (13)0.0365 (13)0.0644 (16)0.0032 (10)0.0086 (11)0.0096 (12)
O40.0238 (10)0.0386 (12)0.0454 (12)0.0008 (9)0.0107 (9)0.0061 (10)
O50.0624 (19)0.0472 (17)0.153 (3)0.0073 (14)0.052 (2)0.0183 (19)
O60.0517 (16)0.0362 (14)0.091 (2)0.0029 (12)0.0089 (15)0.0116 (14)
O70.110 (3)0.0486 (17)0.079 (2)0.0015 (17)0.016 (2)0.0165 (16)
O80.100 (3)0.086 (2)0.0456 (16)0.004 (2)0.0061 (16)0.0180 (16)
O90.096 (3)0.081 (2)0.091 (3)0.020 (2)0.018 (2)0.020 (2)
O100.136 (4)0.075 (2)0.075 (2)0.006 (2)0.039 (2)0.0075 (19)
O110.217 (5)0.052 (2)0.069 (2)0.007 (3)0.013 (3)0.0136 (17)
O120.249 (7)0.069 (3)0.138 (4)0.022 (4)0.019 (4)0.021 (3)
C10.0242 (14)0.0406 (18)0.0358 (16)0.0004 (12)0.0062 (12)0.0091 (13)
C20.0240 (14)0.0351 (16)0.0331 (15)0.0026 (12)0.0083 (12)0.0021 (12)
C30.046 (2)0.0395 (18)0.048 (2)0.0048 (15)0.0188 (16)0.0031 (15)
C40.0244 (14)0.0390 (16)0.0316 (15)0.0010 (12)0.0071 (12)0.0042 (12)
C50.0257 (14)0.0332 (15)0.0325 (15)0.0005 (12)0.0056 (12)0.0020 (12)
C60.0221 (13)0.0342 (15)0.0322 (15)0.0001 (11)0.0061 (11)0.0022 (12)
C70.0238 (14)0.0345 (15)0.0353 (15)0.0014 (12)0.0074 (12)0.0014 (12)
C80.0332 (15)0.0333 (16)0.0347 (15)0.0039 (12)0.0113 (13)0.0043 (12)
C90.0279 (14)0.0410 (17)0.0351 (16)0.0068 (13)0.0101 (13)0.0053 (13)
C100.0342 (15)0.0287 (15)0.0372 (16)0.0034 (12)0.0085 (13)0.0033 (12)
C110.0324 (16)0.0399 (18)0.0496 (19)0.0067 (14)0.0119 (14)0.0108 (15)
C120.0388 (18)0.0410 (18)0.050 (2)0.0109 (15)0.0072 (15)0.0112 (15)
C130.065 (2)0.0342 (17)0.0383 (18)0.0012 (16)0.0208 (17)0.0040 (14)
C140.0347 (16)0.0336 (16)0.0284 (14)0.0014 (12)0.0089 (12)0.0009 (12)
C150.0294 (15)0.0341 (16)0.0330 (15)0.0004 (12)0.0067 (12)0.0008 (12)
C160.0413 (18)0.0439 (19)0.0346 (16)0.0022 (15)0.0063 (14)0.0096 (14)
C170.0444 (19)0.0393 (18)0.048 (2)0.0079 (15)0.0090 (16)0.0135 (15)
C180.0476 (19)0.0332 (17)0.049 (2)0.0052 (15)0.0122 (16)0.0046 (15)
C190.0404 (17)0.0356 (16)0.0338 (16)0.0012 (14)0.0086 (13)0.0031 (13)
C200.0293 (14)0.0312 (15)0.0312 (15)0.0024 (12)0.0076 (12)0.0023 (12)
C210.053 (2)0.060 (3)0.079 (3)0.006 (2)0.005 (2)0.000 (2)
C220.083 (4)0.091 (4)0.065 (3)0.013 (3)0.011 (3)0.026 (3)
C230.080 (3)0.054 (3)0.067 (3)0.002 (2)0.008 (2)0.001 (2)
Geometric parameters (Å, º) top
Zn1—N4i2.003 (2)C1—C41.503 (4)
Zn1—O4ii2.005 (2)C2—C61.503 (4)
Zn1—O12.011 (2)C3—C81.487 (5)
Zn1—N12.020 (3)C4—C91.384 (4)
N1—C141.317 (4)C4—C51.396 (4)
N1—C201.406 (4)C5—C61.387 (4)
N2—C141.346 (4)C5—H50.9300
N2—C151.376 (4)C6—C71.388 (4)
N2—H20.8600C7—C81.390 (4)
N3—C101.333 (4)C7—H70.9300
N3—C121.368 (4)C8—C91.391 (4)
N3—C131.463 (4)C9—H90.9300
N4—C101.318 (4)C10—H100.9300
N4—C111.379 (4)C11—C121.341 (5)
N4—Zn1iii2.003 (2)C11—H110.9300
N5—C231.310 (6)C12—H120.9300
N5—C211.445 (6)C13—C141.491 (4)
N5—C221.453 (5)C13—H13A0.9700
O1—C11.274 (4)C13—H13B0.9700
O2—C11.235 (4)C15—C161.390 (4)
O3—C21.233 (4)C15—C201.395 (4)
O4—C21.275 (4)C16—C171.376 (5)
O4—Zn1iv2.005 (2)C16—H160.9300
O5—C31.203 (4)C17—C181.400 (5)
O6—C31.313 (4)C17—H170.9300
O6—H60.8200C18—C191.380 (5)
O7—C231.246 (5)C18—H180.9300
O8—H8A0.8500C19—C201.392 (4)
O8—H8B0.8499C19—H190.9300
O9—H9A0.8499C21—H21A0.9600
O9—H9B0.8500C21—H21B0.9600
O10—H10A0.8500C21—H21C0.9600
O10—H10B0.8501C22—H22A0.9600
O11—H11A0.8499C22—H22B0.9600
O11—H11B0.8501C22—H22C0.9600
O12—H12A0.8500C23—H23A0.9300
O12—H12B0.8499
N4i—Zn1—O4ii112.35 (10)C4—C9—H9119.8
N4i—Zn1—O1106.23 (11)C8—C9—H9119.8
O4ii—Zn1—O197.55 (9)N4—C10—N3110.7 (3)
N4i—Zn1—N1128.06 (10)N4—C10—H10124.7
O4ii—Zn1—N1103.50 (10)N3—C10—H10124.7
O1—Zn1—N1104.82 (10)C12—C11—N4109.1 (3)
C14—N1—C20105.7 (2)C12—C11—H11125.4
C14—N1—Zn1132.7 (2)N4—C11—H11125.4
C20—N1—Zn1121.51 (19)C11—C12—N3106.5 (3)
C14—N2—C15108.0 (3)C11—C12—H12126.8
C14—N2—H2126.0N3—C12—H12126.8
C15—N2—H2126.0N3—C13—C14112.0 (3)
C10—N3—C12107.7 (3)N3—C13—H13A109.2
C10—N3—C13126.3 (3)C14—C13—H13A109.2
C12—N3—C13125.9 (3)N3—C13—H13B109.2
C10—N4—C11106.0 (3)C14—C13—H13B109.2
C10—N4—Zn1iii125.1 (2)H13A—C13—H13B107.9
C11—N4—Zn1iii127.4 (2)N1—C14—N2112.2 (3)
C23—N5—C21120.7 (4)N1—C14—C13124.2 (3)
C23—N5—C22120.9 (4)N2—C14—C13123.5 (3)
C21—N5—C22118.4 (4)N2—C15—C16132.1 (3)
C1—O1—Zn1109.0 (2)N2—C15—C20105.7 (3)
C2—O4—Zn1iv106.30 (19)C16—C15—C20122.2 (3)
C3—O6—H6109.5C17—C16—C15116.8 (3)
H8A—O8—H8B101.2C17—C16—H16121.6
H9A—O9—H9B119.3C15—C16—H16121.6
H10A—O10—H10B109.5C16—C17—C18121.2 (3)
H11A—O11—H11B104.7C16—C17—H17119.4
H12A—O12—H12B103.6C18—C17—H17119.4
O2—C1—O1122.8 (3)C19—C18—C17122.1 (3)
O2—C1—C4120.0 (3)C19—C18—H18118.9
O1—C1—C4117.2 (3)C17—C18—H18118.9
O3—C2—O4122.2 (3)C18—C19—C20117.0 (3)
O3—C2—C6119.9 (3)C18—C19—H19121.5
O4—C2—C6117.9 (3)C20—C19—H19121.5
O5—C3—O6122.8 (4)C19—C20—C15120.7 (3)
O5—C3—C8123.4 (3)C19—C20—N1130.9 (3)
O6—C3—C8113.8 (3)C15—C20—N1108.4 (3)
C9—C4—C5118.9 (3)N5—C21—H21A109.5
C9—C4—C1122.0 (3)N5—C21—H21B109.5
C5—C4—C1119.1 (3)H21A—C21—H21B109.5
C6—C5—C4121.1 (3)N5—C21—H21C109.5
C6—C5—H5119.4H21A—C21—H21C109.5
C4—C5—H5119.4H21B—C21—H21C109.5
C5—C6—C7119.4 (3)N5—C22—H22A109.5
C5—C6—C2118.9 (3)N5—C22—H22B109.5
C7—C6—C2121.7 (3)H22A—C22—H22B109.5
C8—C7—C6119.9 (3)N5—C22—H22C109.5
C8—C7—H7120.0H22A—C22—H22C109.5
C6—C7—H7120.0H22B—C22—H22C109.5
C7—C8—C9120.2 (3)O7—C23—N5124.1 (5)
C7—C8—C3121.0 (3)O7—C23—H23A118.0
C9—C8—C3118.8 (3)N5—C23—H23A118.0
C4—C9—C8120.4 (3)
Zn1—O1—C1—O20.7 (4)Zn1iii—N4—C11—C12166.6 (2)
Zn1—O1—C1—C4179.7 (2)N4—C11—C12—N30.1 (4)
Zn1iv—O4—C2—O37.2 (4)C10—N3—C12—C110.4 (4)
Zn1iv—O4—C2—C6172.7 (2)C13—N3—C12—C11177.2 (3)
O2—C1—C4—C9166.1 (3)C10—N3—C13—C14117.6 (4)
O1—C1—C4—C914.3 (4)C12—N3—C13—C1466.1 (4)
O2—C1—C4—C513.4 (4)C20—N1—C14—N20.0 (3)
O1—C1—C4—C5166.2 (3)Zn1—N1—C14—N2175.9 (2)
C9—C4—C5—C60.9 (4)C20—N1—C14—C13177.9 (3)
C1—C4—C5—C6179.6 (3)Zn1—N1—C14—C136.2 (5)
C4—C5—C6—C71.4 (4)C15—N2—C14—N10.5 (4)
C4—C5—C6—C2178.4 (3)C15—N2—C14—C13178.4 (3)
O3—C2—C6—C53.2 (4)N3—C13—C14—N1151.5 (3)
O4—C2—C6—C5176.9 (3)N3—C13—C14—N230.9 (5)
O3—C2—C6—C7177.0 (3)C14—N2—C15—C16178.1 (3)
O4—C2—C6—C72.9 (4)C14—N2—C15—C200.8 (3)
C5—C6—C7—C80.4 (4)N2—C15—C16—C17179.4 (3)
C2—C6—C7—C8179.4 (3)C20—C15—C16—C170.7 (5)
C6—C7—C8—C91.1 (5)C15—C16—C17—C180.9 (5)
C6—C7—C8—C3179.7 (3)C16—C17—C18—C190.6 (6)
O5—C3—C8—C7179.3 (4)C17—C18—C19—C200.0 (5)
O6—C3—C8—C70.4 (5)C18—C19—C20—C150.3 (5)
O5—C3—C8—C91.5 (5)C18—C19—C20—N1178.2 (3)
O6—C3—C8—C9179.6 (3)N2—C15—C20—C19179.0 (3)
C5—C4—C9—C80.6 (4)C16—C15—C20—C190.0 (5)
C1—C4—C9—C8178.9 (3)N2—C15—C20—N10.7 (3)
C7—C8—C9—C41.6 (5)C16—C15—C20—N1178.3 (3)
C3—C8—C9—C4179.2 (3)C14—N1—C20—C19178.5 (3)
C11—N4—C10—N30.7 (4)Zn1—N1—C20—C192.0 (4)
Zn1iii—N4—C10—N3167.3 (2)C14—N1—C20—C150.5 (3)
C12—N3—C10—N40.7 (4)Zn1—N1—C20—C15176.02 (19)
C13—N3—C10—N4177.6 (3)C21—N5—C23—O71.5 (7)
C10—N4—C11—C120.5 (4)C22—N5—C23—O7176.7 (5)
Symmetry codes: (i) x, y+3/2, z1/2; (ii) x+1, y, z; (iii) x, y+3/2, z+1/2; (iv) x1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O80.861.872.702 (4)162
O6—H6···O70.821.812.631 (4)176
O9—H9A···O20.851.882.728 (4)180
O10—H10A···O90.852.102.900 (6)157
O11—H11B···O40.852.092.938 (4)173
O12—H12A···O30.852.022.696 (5)136
O8—H8A···O10iii0.852.012.788 (5)151
O8—H8B···O12v0.852.112.927 (7)161
O9—H9B···O7vi0.852.293.117 (5)163
O10—H10B···O11vi0.851.912.757 (5)172
O12—H12B···O7vi0.852.283.030 (7)147
O11—H11A···O1vii0.852.393.033 (5)133
Symmetry codes: (iii) x, y+3/2, z+1/2; (v) x+1, y+3/2, z+1/2; (vi) x+1, y+1/2, z+3/2; (vii) x+1, y+1, z+1.
 

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