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In recent years, N-heterocyclic carboxyl­ate ligands have attracted much inter­est in the preparation of new coordination polymers since they contain N-atom donors, as well as O-atom donors, and have a rich variety of coordination modes which can lead to polymers with intriguing structures and inter­esting properties. A new two-dimensional coordination polymer, namely poly[[μ3-2,2′-(1,2-phenyl­ene)bis­(4-carboxy-1H-imidazole-5-­carboxyl­ato)-κ6O4,N3,N3′,O4′:O5:O5′]manganese(II)], [Mn(C16H8N4O8)]n or [Mn(H4Phbidc)]n, has been synthesized by the reaction of Mn(OAc)2·4H2O (OAc is acetate) with 2,2′-(1,2-phenyl­ene)bis­(1H-imidazole-4,5-di­carb­oxy­lic acid) (H6Phbidc) under solvothermal conditions. In the polymer, each MnII ion is six-coordinated by two N atoms from one H4Phbidc2− ligand and by four O atoms from three H4Phbidc2− ligands, forming a significantly distorted octa­hedral MnN2O4 coordination geometry. The MnII ions are linked by hexa­dentate H4Phbidc2− ligands, leading to a two-di­mensional structure parallel to the ac plane. In the crystal, adjacent layers are further connected by N—H...O hydrogen bonds, forming a three-dimensional structure in the solid state.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229618005508/sk3685sup1.cif
Contains datablocks I, Yang

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618005508/sk3685Isup2.hkl
Contains datablock I

CCDC reference: 1835840

Computing details top

Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); 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[[µ3-2,2'-(1,2-phenylene)bis(4-carboxy-1H-imidazole-5-carboxylato)-κ6O4,N3,N3',O4':O5:O5':]manganese(II)] top
Crystal data top
[Mn(C16H8N4O8)]F(000) = 884
Mr = 439.20Dx = 1.792 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 8.3422 (4) ÅCell parameters from 9920 reflections
b = 16.4500 (8) Åθ = 2.5–27.5°
c = 11.8773 (5) ŵ = 0.87 mm1
β = 93.108 (2)°T = 293 K
V = 1627.51 (13) Å3Block, yellow
Z = 40.21 × 0.18 × 0.15 mm
Data collection top
Bruker D8 VENTURE PHOTON
diffractometer
3244 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.031
φ and ω scansθmax = 27.6°, θmin = 3.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 1010
k = 2121
22393 measured reflectionsl = 1514
3753 independent reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.031H-atom parameters constrained
wR(F2) = 0.084 w = 1/[σ2(Fo2) + (0.0394P)2 + 0.9243P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.001
3753 reflectionsΔρmax = 0.30 e Å3
264 parametersΔρmin = 0.36 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
Mn11.00156 (3)0.56363 (2)0.17925 (2)0.02691 (9)
N10.47745 (17)0.61064 (9)0.11776 (13)0.0300 (3)
H1A0.39090.63710.10010.036*
N20.73381 (17)0.58357 (9)0.15029 (13)0.0286 (3)
N30.96790 (17)0.68247 (9)0.25923 (13)0.0283 (3)
N40.91528 (18)0.80371 (9)0.32423 (13)0.0297 (3)
H4A0.87330.85120.32930.036*
O10.21031 (16)0.50309 (11)0.13295 (15)0.0541 (4)
O20.37463 (18)0.40264 (10)0.18115 (15)0.0511 (4)
O30.66409 (18)0.37515 (9)0.22286 (16)0.0504 (4)
H30.56700.38290.21480.076*
O40.88557 (16)0.44914 (8)0.22465 (13)0.0376 (3)
O51.0169 (2)0.88073 (9)0.51987 (12)0.0450 (4)
O61.20124 (17)0.78402 (9)0.55902 (13)0.0430 (4)
O71.2319 (2)0.63322 (10)0.50006 (14)0.0500 (4)
H71.21740.67880.52560.075*
O81.1452 (2)0.56090 (9)0.35227 (14)0.0516 (4)
C10.3454 (2)0.47588 (13)0.15565 (17)0.0357 (4)
C20.4861 (2)0.53054 (11)0.14972 (16)0.0292 (4)
C30.6466 (2)0.51509 (10)0.17001 (15)0.0278 (4)
C40.7387 (2)0.44240 (11)0.20821 (17)0.0319 (4)
C50.6292 (2)0.64095 (10)0.11886 (15)0.0267 (3)
C60.6667 (2)0.72430 (11)0.08298 (16)0.0285 (4)
C70.5793 (2)0.75560 (13)0.01030 (17)0.0372 (4)
H7A0.50060.72370.04710.045*
C80.6074 (3)0.83341 (14)0.04936 (19)0.0443 (5)
H8A0.54800.85320.11200.053*
C90.7227 (3)0.88147 (13)0.00409 (19)0.0441 (5)
H9A0.74150.93360.02230.053*
C100.8105 (2)0.85196 (12)0.09733 (17)0.0364 (4)
H10A0.88770.88490.13370.044*
C110.7854 (2)0.77349 (10)0.13806 (15)0.0277 (4)
C120.8843 (2)0.75027 (10)0.23927 (15)0.0268 (4)
C131.0855 (2)0.81509 (12)0.50117 (16)0.0339 (4)
C141.0233 (2)0.77016 (11)0.40019 (16)0.0295 (4)
C151.0542 (2)0.69432 (11)0.35922 (16)0.0289 (4)
C161.1485 (2)0.62510 (12)0.40453 (17)0.0370 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Mn10.02126 (14)0.01983 (14)0.03941 (17)0.00174 (10)0.00045 (10)0.00094 (10)
N10.0189 (7)0.0265 (8)0.0441 (9)0.0031 (6)0.0036 (6)0.0018 (7)
N20.0211 (7)0.0220 (7)0.0422 (9)0.0000 (6)0.0011 (6)0.0008 (6)
N30.0238 (7)0.0231 (7)0.0376 (8)0.0025 (6)0.0019 (6)0.0020 (6)
N40.0291 (8)0.0211 (7)0.0388 (8)0.0039 (6)0.0005 (6)0.0036 (6)
O10.0196 (7)0.0658 (11)0.0769 (11)0.0004 (7)0.0040 (7)0.0189 (9)
O20.0369 (8)0.0361 (8)0.0805 (11)0.0154 (7)0.0058 (8)0.0016 (8)
O30.0363 (8)0.0257 (7)0.0889 (12)0.0051 (6)0.0007 (8)0.0100 (7)
O40.0256 (6)0.0252 (7)0.0619 (9)0.0041 (5)0.0012 (6)0.0073 (6)
O50.0575 (10)0.0366 (8)0.0409 (8)0.0083 (7)0.0017 (7)0.0085 (6)
O60.0341 (7)0.0457 (9)0.0479 (8)0.0015 (6)0.0079 (6)0.0106 (7)
O70.0487 (9)0.0429 (9)0.0557 (10)0.0125 (7)0.0220 (7)0.0079 (7)
O80.0601 (10)0.0331 (8)0.0589 (10)0.0181 (7)0.0213 (8)0.0081 (7)
C10.0257 (9)0.0376 (11)0.0440 (11)0.0056 (8)0.0054 (8)0.0089 (8)
C20.0215 (8)0.0249 (9)0.0409 (10)0.0003 (7)0.0006 (7)0.0030 (7)
C30.0221 (8)0.0220 (8)0.0392 (10)0.0017 (6)0.0009 (7)0.0015 (7)
C40.0274 (9)0.0232 (9)0.0454 (11)0.0004 (7)0.0036 (8)0.0006 (7)
C50.0209 (8)0.0230 (8)0.0358 (9)0.0010 (6)0.0024 (6)0.0016 (7)
C60.0242 (8)0.0233 (8)0.0379 (10)0.0039 (7)0.0016 (7)0.0007 (7)
C70.0308 (9)0.0361 (10)0.0439 (11)0.0022 (8)0.0057 (8)0.0035 (9)
C80.0435 (12)0.0436 (12)0.0451 (12)0.0087 (9)0.0042 (9)0.0131 (9)
C90.0499 (12)0.0288 (10)0.0536 (13)0.0032 (9)0.0029 (10)0.0119 (9)
C100.0400 (10)0.0230 (9)0.0459 (11)0.0019 (8)0.0007 (8)0.0004 (8)
C110.0254 (8)0.0215 (8)0.0361 (9)0.0037 (7)0.0016 (7)0.0006 (7)
C120.0236 (8)0.0202 (8)0.0368 (9)0.0001 (6)0.0018 (7)0.0006 (7)
C130.0308 (9)0.0347 (10)0.0366 (10)0.0028 (8)0.0041 (8)0.0045 (8)
C140.0249 (8)0.0279 (9)0.0359 (9)0.0007 (7)0.0037 (7)0.0025 (7)
C150.0221 (8)0.0274 (9)0.0370 (9)0.0008 (7)0.0005 (7)0.0024 (7)
C160.0318 (10)0.0324 (10)0.0461 (11)0.0059 (8)0.0062 (8)0.0027 (8)
Geometric parameters (Å, º) top
Mn1—O1i2.1049 (15)O5—Mn1iv2.1128 (14)
Mn1—O5ii2.1128 (14)O6—C131.262 (2)
Mn1—O42.1979 (13)O7—C161.305 (2)
Mn1—N32.1982 (15)O7—H70.8200
Mn1—N22.2654 (14)O8—C161.225 (2)
Mn1—O82.3225 (16)C1—C21.484 (2)
N1—C51.360 (2)C2—C31.372 (2)
N1—C21.372 (2)C3—C41.479 (2)
N1—H1A0.8600C5—C61.474 (2)
N2—C51.325 (2)C6—C71.392 (3)
N2—C31.368 (2)C6—C111.412 (2)
N3—C121.330 (2)C7—C81.386 (3)
N3—C151.369 (2)C7—H7A0.9300
N4—C121.353 (2)C8—C91.374 (3)
N4—C141.358 (2)C8—H8A0.9300
N4—H4A0.8600C9—C101.382 (3)
O1—C11.229 (2)C9—H9A0.9300
O1—Mn1iii2.1049 (15)C10—C111.398 (3)
O2—C11.263 (3)C10—H10A0.9300
O3—C41.286 (2)C11—C121.471 (2)
O3—H30.8200C13—C141.479 (3)
O4—C41.235 (2)C14—C151.369 (2)
O5—C131.248 (2)C15—C161.469 (3)
O1i—Mn1—O5ii83.09 (7)C2—C3—C4133.59 (16)
O1i—Mn1—O492.30 (6)O4—C4—O3122.63 (17)
O5ii—Mn1—O4129.79 (6)O4—C4—C3118.04 (16)
O1i—Mn1—N3131.34 (6)O3—C4—C3119.34 (17)
O5ii—Mn1—N390.99 (6)N2—C5—N1109.86 (15)
O4—Mn1—N3126.00 (6)N2—C5—C6126.68 (15)
O1i—Mn1—N2148.40 (6)N1—C5—C6123.36 (15)
O5ii—Mn1—N284.75 (6)C7—C6—C11118.75 (17)
O4—Mn1—N273.60 (5)C7—C6—C5117.65 (16)
N3—Mn1—N277.81 (5)C11—C6—C5123.60 (16)
O1i—Mn1—O880.07 (6)C8—C7—C6121.16 (19)
O5ii—Mn1—O8138.39 (6)C8—C7—H7A119.4
O4—Mn1—O888.81 (6)C6—C7—H7A119.4
N3—Mn1—O872.95 (5)C9—C8—C7120.25 (19)
N2—Mn1—O8126.47 (6)C9—C8—H8A119.9
C5—N1—C2108.33 (14)C7—C8—H8A119.9
C5—N1—H1A125.8C8—C9—C10119.70 (19)
C2—N1—H1A125.8C8—C9—H9A120.1
C5—N2—C3106.67 (14)C10—C9—H9A120.1
C5—N2—Mn1140.76 (12)C9—C10—C11121.24 (19)
C3—N2—Mn1112.57 (11)C9—C10—H10A119.4
C12—N3—C15106.34 (14)C11—C10—H10A119.4
C12—N3—Mn1138.32 (12)C10—C11—C6118.89 (17)
C15—N3—Mn1115.34 (11)C10—C11—C12115.76 (16)
C12—N4—C14108.95 (15)C6—C11—C12125.32 (16)
C12—N4—H4A125.5N3—C12—N4109.57 (15)
C14—N4—H4A125.5N3—C12—C11128.97 (16)
C1—O1—Mn1iii151.27 (16)N4—C12—C11121.12 (15)
C4—O3—H3109.5O5—C13—O6126.74 (18)
C4—O4—Mn1118.96 (12)O5—C13—C14115.65 (18)
C13—O5—Mn1iv125.81 (13)O6—C13—C14117.61 (17)
C16—O7—H7109.5N4—C14—C15105.38 (16)
C16—O8—Mn1115.36 (13)N4—C14—C13121.80 (16)
O1—C1—O2124.28 (19)C15—C14—C13132.80 (18)
O1—C1—C2119.18 (19)C14—C15—N3109.75 (16)
O2—C1—C2116.51 (17)C14—C15—C16133.11 (17)
C3—C2—N1105.23 (15)N3—C15—C16116.97 (16)
C3—C2—C1130.33 (17)O8—C16—O7121.70 (18)
N1—C2—C1124.42 (16)O8—C16—C15119.05 (17)
N2—C3—C2109.91 (15)O7—C16—C15119.24 (18)
N2—C3—C4116.50 (15)
Mn1iii—O1—C1—O296.8 (4)C9—C10—C11—C12178.72 (19)
Mn1iii—O1—C1—C285.4 (4)C7—C6—C11—C100.3 (3)
C5—N1—C2—C30.3 (2)C5—C6—C11—C10179.61 (17)
C5—N1—C2—C1178.19 (17)C7—C6—C11—C12178.13 (18)
O1—C1—C2—C3179.6 (2)C5—C6—C11—C121.8 (3)
O2—C1—C2—C31.6 (3)C15—N3—C12—N40.4 (2)
O1—C1—C2—N11.5 (3)Mn1—N3—C12—N4179.42 (13)
O2—C1—C2—N1176.52 (18)C15—N3—C12—C11172.85 (17)
C5—N2—C3—C20.4 (2)Mn1—N3—C12—C117.3 (3)
Mn1—N2—C3—C2179.20 (12)C14—N4—C12—N30.9 (2)
C5—N2—C3—C4179.12 (16)C14—N4—C12—C11172.96 (16)
Mn1—N2—C3—C41.3 (2)C10—C11—C12—N3132.8 (2)
N1—C2—C3—N20.4 (2)C6—C11—C12—N349.3 (3)
C1—C2—C3—N2177.96 (19)C10—C11—C12—N439.8 (2)
N1—C2—C3—C4179.0 (2)C6—C11—C12—N4138.15 (18)
C1—C2—C3—C42.7 (4)Mn1iv—O5—C13—O626.7 (3)
Mn1—O4—C4—O3173.51 (16)Mn1iv—O5—C13—C14153.52 (14)
Mn1—O4—C4—C36.4 (2)C12—N4—C14—C151.0 (2)
N2—C3—C4—O43.2 (3)C12—N4—C14—C13177.94 (16)
C2—C3—C4—O4176.1 (2)O5—C13—C14—N49.3 (3)
N2—C3—C4—O3176.66 (18)O6—C13—C14—N4170.52 (17)
C2—C3—C4—O34.0 (3)O5—C13—C14—C15172.1 (2)
C3—N2—C5—N10.2 (2)O6—C13—C14—C158.1 (3)
Mn1—N2—C5—N1179.20 (14)N4—C14—C15—N30.8 (2)
C3—N2—C5—C6176.61 (17)C13—C14—C15—N3178.01 (19)
Mn1—N2—C5—C62.8 (3)N4—C14—C15—C16174.1 (2)
C2—N1—C5—N20.1 (2)C13—C14—C15—C167.1 (4)
C2—N1—C5—C6176.50 (17)C12—N3—C15—C140.3 (2)
N2—C5—C6—C7136.9 (2)Mn1—N3—C15—C14179.88 (12)
N1—C5—C6—C739.1 (3)C12—N3—C15—C16175.60 (16)
N2—C5—C6—C1143.2 (3)Mn1—N3—C15—C164.3 (2)
N1—C5—C6—C11140.84 (18)Mn1—O8—C16—O7176.34 (16)
C11—C6—C7—C80.2 (3)Mn1—O8—C16—C154.6 (3)
C5—C6—C7—C8179.94 (19)C14—C15—C16—O8174.3 (2)
C6—C7—C8—C90.2 (3)N3—C15—C16—O80.4 (3)
C7—C8—C9—C100.1 (3)C14—C15—C16—O74.8 (3)
C8—C9—C10—C110.6 (3)N3—C15—C16—O7179.49 (18)
C9—C10—C11—C60.7 (3)
Symmetry codes: (i) x+1, y, z; (ii) x, y+3/2, z1/2; (iii) x1, y, z; (iv) x, y+3/2, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O20.821.672.480 (2)172
O7—H7···O60.821.782.594 (2)170
N1—H1A···O6v0.862.082.937 (2)172
N4—H4A···O2vi0.862.232.913 (2)136
Symmetry codes: (v) x1, y+3/2, z1/2; (vi) x+1, y+1/2, z+1/2.
 

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