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Two new Zn2+-based metal–organic frameworks (MOFs) based on biphenyl-2,2′,5,5′-tetra­carb­oxy­lic acid, i.e. H4(o,m-bpta), and N-donor ligands, namely, poly[[(μ4-biphenyl-2,2′,5,5′-tetra­carboxyl­ato)bis{[1,3-phenyl­enebis(methyl­ene)]bis­(1H-imidazole)}dizinc(II)] di­methyl­formamide monosolvate dihydrate], {[Zn2(C16H6O8)(C14H14N4)2]·C3H7NO·2H2O}n or {[Zn2(o,m-bpta)(1,3-bimb)2]·C3H7NO·2H2O}n (1) {1,3-bimb = [1,3-phenyl­enebis(methyl­ene)]bis­(1H-imidazole)}, and poly[[(μ4-biphenyl-2,2′,5,5′-tetra­carboxyl­ato)bis{[1,4-phenyl­ene­bis(methyl­ene)]bis­(1H-imidazole)}dizinc(II)] monohydrate], {[Zn2(C16H6O8)(C14H14N4)2]·H2O}n or {[Zn2(o,m-bpta)(1,4-bimb)2]·H2O}n (2) {1,4-bimb = [1,4-phenyl­enebis(methyl­ene)]bis­(1H-imidazole)}, have been synthesized under solvothermal conditions. The com­plexes were characterized by IR spectroscopy, elemental analysis, single-crystal X-ray diffraction and powder X-ray diffraction analysis. Structurally, the (o,m-bpta)4− ligands are fully deprotonated and com­bine with Zn2+ ions in μ4-coordination modes. Com­plex 1 is a (3,4)-connected porous network with honeycomb-like [Zn2(o,m-bpta)]n sheets formed by 4-connected (o,m-bpta)4− ligands. Com­plex 2 exhibits a (2,4)-con­­nected network formed by 4-connected (o,m-bpta)4− ligands linking Zn2+ ions in left-handed helical chains. The cis-configured 1,3-bimb and 1,4-bimb ligands bridge Zn2+ ions to form multi-membered [Zn2(bimb)2] loops. Optically, the com­plexes show strong fluorescence and display larger red shifts compared to free H4(o,m-bpta). Com­plex 2 shows ferroelectric properties due to crystallizing in the C2v polar point group.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S205322962000604X/ef3007sup1.cif
Contains datablocks sf170323a-15_a_sq, sf170602b-43_a, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205322962000604X/ef3007sf170323a-15_a_sqsup2.hkl
Contains datablock sf170323a-15_a_sq

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205322962000604X/ef3007sf170602b-43_asup3.hkl
Contains datablock sf170602b-43_a

tif

Tagged Image Format File (TIF) image https://doi.org/10.1107/S205322962000604X/ef3007sup4.tif
IR spectra

CCDC references: 2000655; 2000654

Computing details top

For both structures, data collection: APEX3 (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015). Molecular graphics: SHELXTL (Sheldrick, 2008), DIAMOND (Brandenburg, 2005) and PLATON (Spek, 2020) for sf170323a-15_a_sq; SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 2005) for sf170602b-43_a. For both structures, software used to prepare material for publication: publCIF (Westrip, 2010).

Poly[[(µ4-biphenyl-2,2',5,5'-tetracarboxylato)bis{[1,3-phenylenebis(methylene)]bis(1H-imidazole)}dizinc(II)] dimethylformamide monosolvate dihydrate] (sf170323a-15_a_sq) top
Crystal data top
[Zn2(C16H6O8)(C14H14N4)2]·C3H7NO·2H2OF(000) = 1912
Mr = 1042.34Dx = 1.358 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 12.3143 (14) ÅCell parameters from 8069 reflections
b = 16.3192 (19) Åθ = 2.7–21.7°
c = 23.367 (3) ŵ = 1.11 mm1
β = 103.545 (3)°T = 296 K
V = 4565.3 (9) Å3Block, colourless
Z = 40.32 × 0.30 × 0.30 mm
Data collection top
Bruker Quest APEX III
diffractometer
2808 reflections with I > 2σ(I)
Radiation source: sealed tubeRint = 0.099
φ and ω scansθmax = 26.5°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Bruker, 2012)
h = 1515
Tmin = 0.654, Tmax = 0.745k = 2020
37836 measured reflectionsl = 2929
4709 independent reflections
Refinement top
Refinement on F213 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.054H-atom parameters constrained
wR(F2) = 0.117 w = 1/[σ2(Fo2) + (0.0459P)2 + 5.6151P]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.001
4709 reflectionsΔρmax = 0.34 e Å3
289 parametersΔρmin = 0.27 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*/UeqOcc. (<1)
Zn10.58999 (3)0.62562 (3)0.35543 (2)0.04334 (16)
O10.6413 (2)0.53400 (16)0.31723 (12)0.0624 (8)
O20.8127 (19)0.5856 (12)0.3472 (8)0.074 (5)0.4
O2'0.8131 (13)0.5609 (9)0.3652 (5)0.075 (3)0.6
O30.8712 (2)0.21893 (16)0.18763 (11)0.0554 (7)
O40.9680 (2)0.30720 (17)0.14785 (12)0.0655 (8)
N10.4261 (2)0.60926 (18)0.34787 (13)0.0435 (8)
N20.2471 (2)0.6334 (2)0.32756 (13)0.0493 (8)
N30.1433 (3)0.7991 (2)0.47281 (13)0.0549 (9)
N40.1406 (2)0.8578 (2)0.55730 (13)0.0520 (9)
C10.7458 (4)0.5309 (3)0.3228 (2)0.0579 (11)
C20.7852 (3)0.4719 (2)0.28289 (17)0.0454 (10)
C30.8971 (3)0.4693 (2)0.28231 (17)0.0469 (10)
H30.9458970.5066880.3050180.056*
C40.9387 (3)0.4125 (2)0.24872 (15)0.0363 (8)
C50.8666 (3)0.3558 (2)0.21582 (15)0.0376 (9)
C60.7532 (3)0.3593 (2)0.21561 (16)0.0492 (10)
H60.7041500.3218010.1932820.059*
C70.7132 (3)0.4173 (3)0.24785 (18)0.0542 (10)
H70.6370260.4199810.2461260.065*
C80.9070 (3)0.2905 (2)0.18075 (15)0.0411 (9)
C90.3778 (3)0.5638 (3)0.3842 (2)0.0667 (13)
H90.4155650.5274560.4126720.080*
C100.2685 (4)0.5792 (3)0.3729 (2)0.0713 (13)
H100.2172410.5571780.3922290.086*
C110.3444 (3)0.6495 (2)0.31421 (15)0.0424 (9)
H110.3528240.6851560.2845010.051*
C120.1406 (3)0.6728 (3)0.30224 (18)0.0698 (13)
H12A0.0834050.6311620.2905350.084*
H12B0.1461920.7029650.2673010.084*
C130.1070 (3)0.7303 (3)0.34523 (18)0.0600 (12)
C140.0141 (3)0.7149 (3)0.36667 (16)0.0548 (11)
H140.0296710.6693030.3531190.066*
C150.0156 (3)0.7651 (3)0.40757 (17)0.0547 (11)
C160.0488 (4)0.8324 (3)0.4280 (3)0.0914 (17)
H160.0279890.8676100.4548830.110*
C170.1459 (5)0.8481 (3)0.4082 (3)0.123 (3)
H170.1915190.8923350.4229550.148*
C180.1728 (5)0.7967 (3)0.3666 (3)0.1001 (19)
H180.2364590.8072240.3528320.120*
C190.1157 (3)0.7407 (3)0.43097 (18)0.0675 (13)
H19A0.1798720.7348190.3980620.081*
H19B0.1011160.6877310.4499900.081*
C200.2117 (4)0.8659 (3)0.46161 (18)0.0680 (13)
H200.2519980.8835090.4249140.082*
C210.2098 (3)0.9012 (3)0.51369 (19)0.0624 (12)
H210.2494820.9478680.5191870.075*
C220.1019 (3)0.7972 (3)0.53078 (17)0.0558 (11)
H220.0517100.7579930.5501090.067*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.0381 (2)0.0553 (3)0.0419 (3)0.0072 (2)0.01987 (19)0.0041 (2)
O10.0487 (17)0.0572 (18)0.094 (2)0.0108 (14)0.0423 (15)0.0036 (16)
O20.065 (7)0.081 (10)0.088 (12)0.002 (7)0.040 (9)0.030 (8)
O2'0.065 (5)0.104 (8)0.060 (5)0.019 (5)0.022 (4)0.014 (5)
O30.0703 (19)0.0457 (17)0.0585 (17)0.0004 (14)0.0315 (15)0.0025 (14)
O40.0709 (19)0.073 (2)0.0656 (19)0.0252 (16)0.0415 (16)0.0198 (15)
N10.0398 (18)0.046 (2)0.0491 (18)0.0028 (15)0.0199 (16)0.0018 (15)
N20.0331 (17)0.069 (2)0.0484 (19)0.0017 (17)0.0153 (14)0.0024 (18)
N30.0430 (19)0.089 (3)0.0377 (19)0.0040 (19)0.0194 (16)0.0050 (19)
N40.0403 (18)0.079 (3)0.0406 (18)0.0075 (17)0.0172 (16)0.0058 (18)
C10.062 (3)0.053 (3)0.069 (3)0.018 (2)0.035 (3)0.009 (2)
C20.040 (2)0.045 (2)0.060 (2)0.0106 (19)0.0272 (19)0.010 (2)
C30.043 (2)0.034 (2)0.070 (3)0.0000 (17)0.025 (2)0.0002 (19)
C40.0323 (18)0.0287 (19)0.052 (2)0.0032 (16)0.0186 (18)0.0061 (18)
C50.036 (2)0.038 (2)0.040 (2)0.0014 (16)0.0135 (17)0.0063 (17)
C60.034 (2)0.062 (3)0.053 (2)0.0024 (19)0.0121 (18)0.003 (2)
C70.035 (2)0.071 (3)0.061 (3)0.006 (2)0.020 (2)0.008 (2)
C80.033 (2)0.051 (3)0.037 (2)0.0030 (18)0.0056 (17)0.0010 (18)
C90.058 (3)0.060 (3)0.088 (3)0.010 (2)0.029 (2)0.034 (3)
C100.053 (3)0.080 (3)0.089 (3)0.004 (2)0.034 (3)0.026 (3)
C110.037 (2)0.056 (3)0.038 (2)0.0002 (18)0.0176 (18)0.0013 (18)
C120.041 (2)0.118 (4)0.053 (3)0.008 (3)0.017 (2)0.002 (3)
C130.039 (2)0.083 (3)0.064 (3)0.010 (2)0.025 (2)0.009 (2)
C140.036 (2)0.089 (3)0.040 (2)0.001 (2)0.0099 (18)0.004 (2)
C150.044 (2)0.075 (3)0.052 (2)0.003 (2)0.023 (2)0.006 (2)
C160.105 (4)0.064 (3)0.134 (5)0.005 (3)0.085 (4)0.011 (3)
C170.138 (5)0.070 (4)0.202 (7)0.035 (3)0.120 (5)0.029 (4)
C180.103 (4)0.077 (4)0.153 (5)0.009 (3)0.097 (4)0.004 (4)
C190.053 (3)0.105 (4)0.052 (3)0.010 (2)0.027 (2)0.009 (3)
C200.059 (3)0.103 (4)0.041 (2)0.014 (3)0.007 (2)0.015 (3)
C210.052 (3)0.081 (3)0.054 (3)0.015 (2)0.014 (2)0.014 (2)
C220.044 (2)0.087 (3)0.040 (2)0.011 (2)0.017 (2)0.013 (2)
Geometric parameters (Å, º) top
Zn1—O11.923 (3)C5—C81.498 (5)
Zn1—O3i1.945 (2)C6—C71.372 (5)
Zn1—N12.002 (3)C6—H60.9300
Zn1—N4ii2.006 (3)C7—H70.9300
O1—C11.263 (5)C9—C101.333 (5)
O2—O2'0.58 (2)C9—H90.9300
O2—C11.257 (16)C10—H100.9300
O2'—C11.234 (13)C11—H110.9300
O3—C81.272 (4)C12—C131.502 (6)
O4—C81.225 (4)C12—H12A0.9700
N1—C111.301 (4)C12—H12B0.9700
N1—C91.365 (4)C13—C141.375 (5)
N2—C111.333 (4)C13—C181.376 (6)
N2—C101.358 (5)C14—C151.372 (5)
N2—C121.457 (5)C14—H140.9300
N3—C221.331 (5)C15—C161.373 (6)
N3—C201.366 (5)C15—C191.514 (5)
N3—C191.460 (5)C16—C171.403 (6)
N4—C221.314 (5)C16—H160.9300
N4—C211.364 (5)C17—C181.382 (7)
C1—C21.499 (5)C17—H170.9300
C2—C71.382 (5)C18—H180.9300
C2—C31.382 (5)C19—H19A0.9700
C3—C41.388 (4)C19—H19B0.9700
C3—H30.9300C20—C211.342 (5)
C4—C51.383 (5)C20—H200.9300
C4—C4iii1.498 (6)C21—H210.9300
C5—C61.396 (5)C22—H220.9300
O1—Zn1—O3i102.79 (11)C10—C9—N1110.0 (4)
O1—Zn1—N1106.83 (12)C10—C9—H9125.0
O3i—Zn1—N1115.04 (12)N1—C9—H9125.0
O1—Zn1—N4ii121.29 (13)C9—C10—N2106.2 (3)
O3i—Zn1—N4ii111.37 (12)C9—C10—H10126.9
N1—Zn1—N4ii100.06 (12)N2—C10—H10126.9
C1—O1—Zn1114.9 (3)N1—C11—N2111.7 (3)
O2'—O2—C174 (3)N1—C11—H11124.2
O2—O2'—C179 (3)N2—C11—H11124.2
C8—O3—Zn1iv121.3 (2)N2—C12—C13111.5 (3)
C11—N1—C9105.2 (3)N2—C12—H12A109.3
C11—N1—Zn1127.4 (2)C13—C12—H12A109.3
C9—N1—Zn1126.5 (3)N2—C12—H12B109.3
C11—N2—C10106.9 (3)C13—C12—H12B109.3
C11—N2—C12126.3 (3)H12A—C12—H12B108.0
C10—N2—C12126.6 (3)C14—C13—C18118.8 (4)
C22—N3—C20106.6 (3)C14—C13—C12120.8 (4)
C22—N3—C19125.0 (4)C18—C13—C12120.3 (4)
C20—N3—C19128.5 (4)C15—C14—C13121.7 (4)
C22—N4—C21105.7 (3)C15—C14—H14119.2
C22—N4—Zn1ii121.4 (3)C13—C14—H14119.2
C21—N4—Zn1ii132.9 (3)C14—C15—C16119.6 (4)
O2'—C1—O1122.9 (9)C14—C15—C19117.8 (4)
O2—C1—O1124.2 (12)C16—C15—C19122.5 (4)
O2'—C1—C2120.0 (9)C15—C16—C17119.9 (5)
O2—C1—C2117.7 (12)C15—C16—H16120.1
O1—C1—C2115.6 (4)C17—C16—H16120.1
C7—C2—C3118.6 (3)C18—C17—C16119.0 (5)
C7—C2—C1121.8 (3)C18—C17—H17120.5
C3—C2—C1119.6 (4)C16—C17—H17120.5
C2—C3—C4121.7 (3)C13—C18—C17121.0 (4)
C2—C3—H3119.1C13—C18—H18119.5
C4—C3—H3119.1C17—C18—H18119.5
C5—C4—C3119.2 (3)N3—C19—C15114.0 (4)
C5—C4—C4iii122.1 (3)N3—C19—H19A108.7
C3—C4—C4iii118.6 (3)C15—C19—H19A108.7
C4—C5—C6119.0 (3)N3—C19—H19B108.7
C4—C5—C8121.8 (3)C15—C19—H19B108.7
C6—C5—C8119.1 (3)H19A—C19—H19B107.6
C7—C6—C5121.0 (4)C21—C20—N3106.9 (4)
C7—C6—H6119.5C21—C20—H20126.6
C5—C6—H6119.5N3—C20—H20126.6
C6—C7—C2120.4 (3)C20—C21—N4109.3 (4)
C6—C7—H7119.8C20—C21—H21125.4
C2—C7—H7119.8N4—C21—H21125.4
O4—C8—O3124.4 (3)N4—C22—N3111.6 (4)
O4—C8—C5121.1 (3)N4—C22—H22124.2
O3—C8—C5114.5 (3)N3—C22—H22124.2
O2—O2'—C1—O1102 (4)N1—C9—C10—N21.8 (5)
O2—O2'—C1—C293 (4)C11—N2—C10—C91.1 (5)
O2'—O2—C1—O196 (4)C12—N2—C10—C9175.5 (4)
O2'—O2—C1—C2102 (4)C9—N1—C11—N21.0 (4)
Zn1—O1—C1—O2'27.1 (9)Zn1—N1—C11—N2168.7 (2)
Zn1—O1—C1—O25.3 (11)C10—N2—C11—N10.1 (4)
Zn1—O1—C1—C2166.9 (3)C12—N2—C11—N1174.5 (4)
O2'—C1—C2—C7158.5 (7)C11—N2—C12—C13107.0 (4)
O2—C1—C2—C7170.7 (10)C10—N2—C12—C1366.3 (6)
O1—C1—C2—C77.9 (6)N2—C12—C13—C14114.4 (4)
O2'—C1—C2—C319.1 (9)N2—C12—C13—C1861.5 (6)
O2—C1—C2—C311.7 (12)C18—C13—C14—C151.6 (7)
O1—C1—C2—C3174.5 (3)C12—C13—C14—C15177.6 (4)
C7—C2—C3—C41.6 (5)C13—C14—C15—C160.2 (6)
C1—C2—C3—C4176.1 (3)C13—C14—C15—C19176.8 (4)
C2—C3—C4—C51.3 (5)C14—C15—C16—C171.8 (8)
C2—C3—C4—C4iii178.8 (3)C19—C15—C16—C17174.6 (5)
C3—C4—C5—C62.3 (5)C15—C16—C17—C182.4 (10)
C4iii—C4—C5—C6179.8 (3)C14—C13—C18—C170.9 (8)
C3—C4—C5—C8177.3 (3)C12—C13—C18—C17177.0 (5)
C4iii—C4—C5—C80.2 (5)C16—C17—C18—C131.1 (10)
C4—C5—C6—C70.6 (5)C22—N3—C19—C1589.2 (5)
C8—C5—C6—C7179.0 (3)C20—N3—C19—C1588.9 (5)
C5—C6—C7—C22.2 (6)C14—C15—C19—N3178.1 (4)
C3—C2—C7—C63.3 (6)C16—C15—C19—N35.4 (6)
C1—C2—C7—C6174.3 (4)C22—N3—C20—C210.8 (5)
Zn1iv—O3—C8—O40.6 (5)C19—N3—C20—C21179.1 (4)
Zn1iv—O3—C8—C5178.3 (2)N3—C20—C21—N40.4 (5)
C4—C5—C8—O448.7 (5)C22—N4—C21—C200.1 (5)
C6—C5—C8—O4131.7 (4)Zn1ii—N4—C21—C20176.9 (3)
C4—C5—C8—O3132.3 (3)C21—N4—C22—N30.6 (4)
C6—C5—C8—O347.3 (4)Zn1ii—N4—C22—N3177.8 (2)
C11—N1—C9—C101.7 (5)C20—N3—C22—N40.9 (4)
Zn1—N1—C9—C10168.1 (3)C19—N3—C22—N4179.3 (3)
Symmetry codes: (i) x+3/2, y+1/2, z+1/2; (ii) x+1/2, y+3/2, z+1; (iii) x+2, y, z+1/2; (iv) x+3/2, y1/2, z+1/2.
Poly[[(µ4-biphenyl-2,2',5,5'-tetracarboxylato)bis{[1,4-πhenylenebis(methylene)]bis(1H-imidazole)}dizinc(II)] monohydrate] (sf170602b-43_a) top
Crystal data top
[Zn2(C16H6O8)(C14H14N4)2]·H2ODx = 1.486 Mg m3
Mr = 951.30Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Fdd2Cell parameters from 9983 reflections
a = 12.4360 (7) Åθ = 2.8–23.7°
b = 24.0412 (13) ŵ = 1.19 mm1
c = 28.4613 (15) ÅT = 296 K
V = 8509.3 (8) Å3Block, colourless
Z = 80.35 × 0.32 × 0.30 mm
F(000) = 3904
Data collection top
Bruker Quest APEX III
diffractometer
3544 reflections with I > 2σ(I)
Radiation source: sealed tubeRint = 0.056
φ and ω scansθmax = 26.5°, θmin = 2.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2012)
h = 1515
Tmin = 0.693, Tmax = 0.745k = 3030
36150 measured reflectionsl = 3535
4388 independent reflections
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.051 w = 1/[σ2(Fo2) + (0.0809P)2 + 17.9128P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.133(Δ/σ)max = 0.001
S = 1.01Δρmax = 0.77 e Å3
4388 reflectionsΔρmin = 0.35 e Å3
290 parametersAbsolute structure: Refined as an inversion twin
44 restraintsAbsolute structure parameter: 0.06 (3)
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.

Refinement. Refined as a 2-component inversion twin

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Zn10.65012 (7)0.62783 (3)0.19424 (3)0.0386 (2)
O10.7507 (4)0.5942 (2)0.2384 (2)0.0580 (15)
O20.6024 (6)0.5523 (3)0.2593 (3)0.091 (2)
O31.0113 (4)0.4278 (2)0.40604 (19)0.0471 (13)
O40.9483 (5)0.3567 (2)0.3659 (2)0.0651 (17)
O50.2247 (17)0.7073 (9)0.3335 (7)0.125 (6)0.5
H5A0.1759900.6877820.3437910.188*0.5
H5B0.2455830.6928690.3090300.188*0.5
N10.0573 (5)0.8107 (3)0.2224 (2)0.0447 (15)
N20.0055 (5)0.7265 (3)0.2391 (3)0.0541 (16)
N30.3934 (5)0.5521 (3)0.1310 (3)0.0576 (18)
N40.5476 (5)0.5866 (2)0.1524 (2)0.0430 (14)
C10.7010 (6)0.5586 (4)0.2621 (3)0.054 (2)
C20.7662 (6)0.5209 (3)0.2928 (3)0.0457 (17)
C30.7200 (7)0.4743 (4)0.3124 (3)0.062 (2)
H30.6470290.4672570.3084690.075*
C40.7838 (6)0.4381 (4)0.3383 (3)0.059 (2)
H40.7528100.4066450.3516910.071*
C50.8930 (6)0.4478 (3)0.3446 (2)0.0411 (16)
C60.9406 (5)0.4948 (3)0.3247 (2)0.0323 (13)
C70.8752 (5)0.5306 (3)0.2987 (2)0.0367 (15)
H70.9056150.5620370.2850600.044*
C80.9555 (6)0.4069 (3)0.3735 (3)0.0435 (16)
C90.0331 (7)0.8132 (4)0.2489 (3)0.063 (2)
H90.0675910.8457750.2580870.075*
C100.0650 (7)0.7621 (4)0.2599 (4)0.068 (2)
H100.1240710.7525030.2782590.081*
C110.0790 (6)0.7578 (3)0.2172 (3)0.0455 (17)
H110.1374420.7438270.2005940.055*
C120.0093 (7)0.6659 (4)0.2438 (4)0.067 (2)
H12A0.0820350.6535230.2373670.080*
H12B0.0073450.6561460.2760210.080*
C130.0676 (7)0.6345 (4)0.2113 (3)0.058 (2)
C140.1557 (9)0.6556 (4)0.1897 (6)0.098 (2)
H140.1705980.6933180.1932000.118*
C150.2244 (11)0.6236 (4)0.1627 (6)0.096 (2)
H150.2800600.6402240.1460800.116*
C160.2099 (9)0.5678 (5)0.1608 (5)0.094 (2)
C170.1231 (10)0.5475 (5)0.1799 (5)0.099 (2)
H170.1098810.5094990.1773670.119*
C180.0497 (10)0.5805 (5)0.2039 (5)0.102 (2)
H180.0134970.5645940.2151050.123*
C190.2845 (7)0.5293 (4)0.1349 (5)0.082 (3)
H19A0.2874950.4939390.1511780.099*
H19B0.2563070.5226360.1036050.099*
C200.4433 (9)0.5722 (4)0.0916 (4)0.081 (3)
H200.4171060.5713970.0609670.098*
C210.5361 (8)0.5929 (4)0.1057 (3)0.071 (3)
H210.5865240.6095180.0861520.086*
C220.4601 (6)0.5616 (3)0.1671 (3)0.0494 (18)
H220.4463330.5518730.1981790.059*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.0331 (4)0.0390 (4)0.0438 (4)0.0013 (3)0.0033 (3)0.0115 (4)
O10.047 (3)0.063 (4)0.064 (4)0.003 (3)0.011 (3)0.033 (3)
O20.068 (4)0.098 (4)0.108 (4)0.000 (3)0.026 (3)0.039 (4)
O30.052 (3)0.041 (3)0.049 (3)0.002 (2)0.015 (3)0.007 (2)
O40.067 (4)0.036 (3)0.092 (5)0.002 (3)0.027 (3)0.004 (3)
O50.121 (8)0.131 (8)0.124 (8)0.000 (5)0.000 (5)0.014 (5)
N10.031 (3)0.051 (4)0.052 (4)0.001 (3)0.005 (3)0.007 (3)
N20.040 (3)0.059 (4)0.063 (4)0.004 (3)0.003 (3)0.011 (3)
N30.045 (4)0.041 (4)0.087 (5)0.000 (3)0.014 (4)0.015 (3)
N40.038 (3)0.040 (3)0.051 (4)0.003 (3)0.000 (3)0.006 (3)
C10.036 (4)0.059 (5)0.067 (5)0.001 (4)0.016 (4)0.018 (4)
C20.039 (4)0.045 (4)0.053 (4)0.001 (3)0.009 (3)0.010 (3)
C30.038 (4)0.065 (5)0.083 (6)0.012 (4)0.020 (4)0.023 (5)
C40.043 (4)0.053 (5)0.081 (6)0.013 (4)0.014 (4)0.028 (4)
C50.038 (4)0.039 (4)0.046 (4)0.001 (3)0.008 (3)0.014 (3)
C60.031 (3)0.031 (3)0.035 (3)0.003 (3)0.001 (3)0.003 (3)
C70.038 (3)0.032 (3)0.040 (4)0.002 (3)0.004 (3)0.003 (3)
C80.040 (4)0.040 (4)0.050 (4)0.001 (3)0.001 (3)0.012 (3)
C90.046 (5)0.073 (6)0.069 (6)0.014 (4)0.012 (4)0.008 (5)
C100.044 (5)0.072 (6)0.087 (7)0.008 (4)0.016 (5)0.000 (5)
C110.038 (4)0.053 (5)0.046 (4)0.003 (3)0.002 (3)0.004 (3)
C120.050 (5)0.056 (5)0.094 (7)0.001 (4)0.008 (5)0.016 (5)
C130.048 (4)0.050 (5)0.076 (6)0.002 (4)0.005 (4)0.022 (4)
C140.074 (4)0.060 (4)0.159 (6)0.012 (3)0.039 (4)0.011 (4)
C150.074 (4)0.060 (3)0.155 (6)0.015 (3)0.038 (4)0.014 (4)
C160.075 (4)0.060 (3)0.147 (6)0.021 (3)0.034 (4)0.017 (4)
C170.085 (4)0.068 (3)0.145 (6)0.026 (3)0.041 (4)0.020 (4)
C180.088 (4)0.074 (4)0.146 (6)0.029 (3)0.046 (4)0.022 (4)
C190.045 (5)0.054 (5)0.148 (10)0.008 (4)0.007 (6)0.020 (6)
C200.103 (8)0.074 (7)0.067 (6)0.026 (6)0.034 (6)0.015 (5)
C210.081 (7)0.071 (6)0.061 (6)0.025 (5)0.012 (5)0.017 (5)
C220.040 (4)0.049 (4)0.059 (5)0.000 (3)0.003 (4)0.009 (4)
Geometric parameters (Å, º) top
Zn1—O11.950 (5)C5—C81.499 (9)
Zn1—O3i1.960 (5)C6—C71.396 (9)
Zn1—N42.006 (6)C6—C6iii1.498 (12)
Zn1—N1ii2.039 (7)C7—H70.9300
O1—C11.251 (10)C9—C101.328 (13)
O2—C11.239 (10)C9—H90.9300
O3—C81.262 (9)C10—H100.9300
O4—C81.228 (9)C11—H110.9300
O5—H5A0.8204C12—C131.528 (14)
O5—H5B0.8204C12—H12A0.9700
N1—C111.308 (10)C12—H12B0.9700
N1—C91.356 (10)C13—C181.335 (13)
N2—C111.338 (10)C13—C141.354 (14)
N2—C101.360 (12)C14—C151.383 (16)
N2—C121.463 (11)C14—H140.9300
N3—C221.340 (10)C15—C161.354 (15)
N3—C201.372 (13)C15—H150.9300
N3—C191.464 (11)C16—C171.304 (15)
N4—C221.311 (9)C16—C191.504 (15)
N4—C211.345 (11)C17—C181.391 (16)
C1—C21.497 (10)C17—H170.9300
C2—C31.377 (11)C18—H180.9300
C2—C71.385 (9)C19—H19A0.9700
C3—C41.390 (11)C19—H19B0.9700
C3—H30.9300C20—C211.319 (14)
C4—C51.389 (10)C20—H200.9300
C4—H40.9300C21—H210.9300
C5—C61.397 (9)C22—H220.9300
O1—Zn1—O3i104.6 (2)N1—C9—H9125.1
O1—Zn1—N4125.8 (2)C9—C10—N2106.7 (8)
O3i—Zn1—N4109.4 (2)C9—C10—H10126.7
O1—Zn1—N1ii114.3 (3)N2—C10—H10126.7
O3i—Zn1—N1ii95.3 (2)N1—C11—N2110.7 (7)
N4—Zn1—N1ii103.3 (2)N1—C11—H11124.7
C1—O1—Zn1108.4 (5)N2—C11—H11124.7
C8—O3—Zn1iv118.1 (5)N2—C12—C13114.6 (7)
H5A—O5—H5B107.1N2—C12—H12A108.6
C11—N1—C9106.1 (7)C13—C12—H12A108.6
C11—N1—Zn1ii122.9 (5)N2—C12—H12B108.6
C9—N1—Zn1ii131.0 (6)C13—C12—H12B108.6
C11—N2—C10106.8 (7)H12A—C12—H12B107.6
C11—N2—C12125.4 (8)C18—C13—C14115.4 (10)
C10—N2—C12127.4 (8)C18—C13—C12118.1 (9)
C22—N3—C20106.7 (7)C14—C13—C12126.5 (9)
C22—N3—C19125.4 (9)C13—C14—C15122.9 (10)
C20—N3—C19127.7 (9)C13—C14—H14118.6
C22—N4—C21106.1 (7)C15—C14—H14118.6
C22—N4—Zn1124.4 (6)C16—C15—C14119.5 (11)
C21—N4—Zn1126.8 (5)C16—C15—H15120.2
O2—C1—O1122.5 (7)C14—C15—H15120.2
O2—C1—C2120.0 (7)C17—C16—C15117.7 (12)
O1—C1—C2117.4 (6)C17—C16—C19119.0 (10)
C3—C2—C7119.7 (7)C15—C16—C19123.2 (10)
C3—C2—C1120.2 (7)C16—C17—C18122.3 (10)
C7—C2—C1119.9 (7)C16—C17—H17118.9
C2—C3—C4119.1 (7)C18—C17—H17118.9
C2—C3—H3120.4C13—C18—C17121.6 (10)
C4—C3—H3120.4C13—C18—H18119.2
C5—C4—C3121.4 (7)C17—C18—H18119.2
C5—C4—H4119.3N3—C19—C16112.2 (8)
C3—C4—H4119.3N3—C19—H19A109.2
C4—C5—C6119.8 (6)C16—C19—H19A109.2
C4—C5—C8117.9 (6)N3—C19—H19B109.2
C6—C5—C8122.3 (6)C16—C19—H19B109.2
C7—C6—C5117.8 (6)H19A—C19—H19B107.9
C7—C6—C6iii118.2 (6)C21—C20—N3106.1 (8)
C5—C6—C6iii123.5 (7)C21—C20—H20126.9
C2—C7—C6122.1 (6)N3—C20—H20126.9
C2—C7—H7119.0C20—C21—N4110.7 (9)
C6—C7—H7119.0C20—C21—H21124.7
O4—C8—O3124.1 (6)N4—C21—H21124.7
O4—C8—C5120.7 (7)N4—C22—N3110.3 (7)
O3—C8—C5115.1 (6)N4—C22—H22124.8
C10—C9—N1109.7 (8)N3—C22—H22124.8
C10—C9—H9125.1
Zn1—O1—C1—O26.7 (12)Zn1ii—N1—C11—N2180.0 (5)
Zn1—O1—C1—C2170.1 (6)C10—N2—C11—N11.2 (9)
O2—C1—C2—C39.5 (13)C12—N2—C11—N1175.0 (8)
O1—C1—C2—C3167.4 (8)C11—N2—C12—C13104.2 (9)
O2—C1—C2—C7174.9 (9)C10—N2—C12—C1383.3 (12)
O1—C1—C2—C78.2 (12)N2—C12—C13—C18162.2 (11)
C7—C2—C3—C40.4 (13)N2—C12—C13—C1419.7 (16)
C1—C2—C3—C4175.9 (9)C18—C13—C14—C152 (2)
C2—C3—C4—C50.1 (15)C12—C13—C14—C15176.6 (13)
C3—C4—C5—C60.1 (14)C13—C14—C15—C166 (3)
C3—C4—C5—C8179.4 (8)C14—C15—C16—C178 (2)
C4—C5—C6—C70.0 (11)C14—C15—C16—C19176.1 (14)
C8—C5—C6—C7179.5 (7)C15—C16—C17—C184 (2)
C4—C5—C6—C6iii172.4 (7)C19—C16—C17—C18179.2 (13)
C8—C5—C6—C6iii8.1 (10)C14—C13—C18—C177 (2)
C3—C2—C7—C60.5 (12)C12—C13—C18—C17171.7 (12)
C1—C2—C7—C6176.1 (7)C16—C17—C18—C134 (2)
C5—C6—C7—C20.3 (10)C22—N3—C19—C1665.1 (13)
C6iii—C6—C7—C2173.1 (6)C20—N3—C19—C16108.6 (13)
Zn1iv—O3—C8—O44.5 (10)C17—C16—C19—N3158.5 (13)
Zn1iv—O3—C8—C5177.9 (5)C15—C16—C19—N326 (2)
C4—C5—C8—O449.1 (11)C22—N3—C20—C210.4 (11)
C6—C5—C8—O4131.4 (8)C19—N3—C20—C21174.3 (8)
C4—C5—C8—O3128.7 (8)N3—C20—C21—N40.3 (12)
C6—C5—C8—O350.8 (10)C22—N4—C21—C200.0 (11)
C11—N1—C9—C100.4 (11)Zn1—N4—C21—C20161.8 (7)
Zn1ii—N1—C9—C10179.0 (6)C21—N4—C22—N30.2 (9)
N1—C9—C10—N21.1 (11)Zn1—N4—C22—N3162.1 (5)
C11—N2—C10—C91.4 (10)C20—N3—C22—N40.4 (9)
C12—N2—C10—C9175.0 (9)C19—N3—C22—N4174.4 (7)
C9—N1—C11—N20.5 (9)
Symmetry codes: (i) x+7/4, y+1/4, z1/4; (ii) x+1/2, y+3/2, z; (iii) x+2, y+1, z; (iv) x+7/4, y1/4, z+1/4.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C22—H22···O20.932.613.172 (11)120
C12—H12B···O4v0.972.633.598 (13)173
C12—H12A···O1vi0.972.523.452 (11)160
C11—H11···O3vii0.932.553.445 (10)162
C11—H11···O3viii0.932.603.062 (9)112
C10—H10···O5ii0.932.633.43 (2)144
C10—H10···O50.932.283.17 (2)160
O5—H5A···O4v0.821.982.80 (2)176
Symmetry codes: (ii) x+1/2, y+3/2, z; (v) x+1, y+1, z; (vi) x1, y, z; (vii) x+3/4, y+1/4, z1/4; (viii) x5/4, y+5/4, z1/4.
 

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