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A novel ZnII coordination polymer, namely, poly[{μ2-bis­[4-(2-methyl-1H-imidazol-1-yl)phen­yl]methanone-κ2N3:N3′}(μ2-5-bromo­ben­zene-1,3-di­carboxyl­ato-κ2O1:O3)zinc(II)], [Zn(C8H3BrO4)(C21H18N4O)]n or [Zn(Br-BDC)(MIPMO)]n, (I), has been synthesized by the solvothermal method using 5-bromo­iso­phthalic acid (Br-H2BDC), bis­[4-(2-methyl-1H-imidazol-1-yl)phen­yl]methanone (MIPMO) and Zn(NO3)2·6H2O. Structure analysis showed that com­pound (I) displays twofold parallel inter­woven sql nets. Fluorescence experiments confirmed that the com­pound can sensitively and selectively detect nitro­furan­toin (NFT) in aqueous medium. In addition, the possible fluorescence quenching mechanisms of com­pound (I) toward NFT are investigated.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229624002171/dg3050sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229624002171/dg3050Isup2.hkl
Contains datablock I

CCDC reference: 2338137

Computing details top

Poly[{µ2-bis[4-(2-methyl-1H-imidazol-1-yl)phenyl]methanone-κ2N3:N3'}(µ2-5-bromobenzene-1,3-dicarboxylato-κ2O1:O3)zinc(II)] top
Crystal data top
[Zn(C8H3BrO4)(C21H18N4O)]F(000) = 1312
Mr = 650.79Dx = 1.565 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 9.730 (5) ÅCell parameters from 9213 reflections
b = 16.520 (9) Åθ = 27.9–2.6°
c = 17.649 (10) ŵ = 2.38 mm1
β = 103.19 (2)°T = 293 K
V = 2762 (3) Å3Block, colorless
Z = 40.19 × 0.18 × 0.17 mm
Data collection top
Bruker APEXII CCD
diffractometer
4729 reflections with I > 2σ(I)
φ and ω scansRint = 0.033
Absorption correction: multi-scan
(SADABS; Bruker, 2016)
θmax = 26.0°, θmin = 2.7°
Tmin = 0.574, Tmax = 0.746h = 1212
49055 measured reflectionsk = 2020
5414 independent reflectionsl = 2121
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036H-atom parameters constrained
wR(F2) = 0.100 w = 1/[σ2(Fo2) + (0.0506P)2 + 3.4737P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
5414 reflectionsΔρmax = 1.67 e Å3
363 parametersΔρmin = 0.44 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
Br10.80325 (4)0.39453 (3)0.00985 (2)0.06071 (14)
Zn10.64911 (3)0.07383 (2)0.23045 (2)0.03041 (10)
O10.7064 (2)0.17720 (12)0.19595 (12)0.0407 (5)
O50.1915 (3)0.29606 (19)0.64997 (13)0.0715 (8)
O20.8412 (3)0.2035 (2)0.31072 (15)0.0860 (11)
O31.2198 (3)0.41302 (17)0.33033 (14)0.0659 (8)
O41.2037 (3)0.49661 (16)0.23089 (14)0.0624 (7)
N40.5036 (2)0.54715 (14)0.36843 (13)0.0336 (5)
N10.5422 (3)0.06977 (14)0.31469 (14)0.0355 (5)
N20.4037 (3)0.09600 (15)0.39234 (15)0.0390 (6)
N30.3168 (2)0.49910 (14)0.44966 (13)0.0337 (5)
C60.8734 (3)0.36893 (19)0.09671 (16)0.0382 (6)
C70.8114 (3)0.30714 (18)0.12851 (16)0.0363 (6)
H70.73530.27900.09850.044*
C20.8634 (3)0.28704 (17)0.20612 (16)0.0344 (6)
C10.8008 (3)0.21777 (19)0.24224 (17)0.0400 (7)
C110.5245 (4)0.00012 (18)0.35423 (18)0.0458 (7)
H110.56600.04960.34880.055*
C120.4381 (4)0.01528 (18)0.4016 (2)0.0497 (8)
H120.40750.02140.43430.060*
C100.4687 (3)0.12690 (17)0.33922 (16)0.0357 (6)
C90.4582 (4)0.2126 (2)0.3144 (2)0.0582 (9)
H9A0.54150.22750.29720.087*
H9B0.44970.24630.35750.087*
H9C0.37670.21970.27260.087*
C130.3314 (3)0.14186 (18)0.44010 (17)0.0385 (6)
C180.1896 (3)0.1584 (2)0.41518 (19)0.0466 (7)
H180.13780.13730.36850.056*
C170.1256 (3)0.2069 (2)0.46097 (19)0.0458 (7)
H170.03010.21910.44480.055*
C160.2032 (3)0.23747 (18)0.53071 (17)0.0377 (6)
C150.3442 (3)0.21629 (18)0.55651 (17)0.0402 (7)
H150.39510.23400.60480.048*
C140.4084 (3)0.16931 (19)0.51076 (18)0.0418 (7)
H140.50340.15600.52730.050*
C190.1427 (3)0.2943 (2)0.58072 (18)0.0437 (7)
C200.0259 (3)0.34936 (18)0.54439 (16)0.0359 (6)
C250.0046 (3)0.37558 (19)0.46738 (17)0.0383 (6)
H250.06500.35850.43670.046*
C240.1064 (3)0.42685 (18)0.43677 (16)0.0373 (6)
H240.11920.44560.38600.045*
C230.1979 (3)0.45003 (17)0.48171 (16)0.0336 (6)
C220.1736 (3)0.42786 (18)0.55926 (17)0.0372 (6)
H220.23270.44620.59030.045*
C210.0610 (3)0.37836 (18)0.58984 (17)0.0388 (6)
H210.04320.36420.64220.047*
C280.3609 (3)0.56550 (18)0.48537 (17)0.0367 (6)
H280.32020.58600.53440.044*
C290.4749 (3)0.59433 (17)0.43441 (17)0.0357 (6)
H290.52670.63950.44260.043*
C270.4069 (3)0.48934 (17)0.37973 (16)0.0345 (6)
C260.4056 (4)0.4208 (2)0.3263 (2)0.0548 (9)
H26A0.50080.40530.30280.082*
H26B0.35680.37590.35480.082*
H26C0.35830.43670.28650.082*
C30.9777 (3)0.32947 (18)0.24916 (16)0.0361 (6)
H31.01350.31570.30100.043*
C41.0394 (3)0.39163 (18)0.21671 (16)0.0359 (6)
C81.1644 (3)0.43647 (19)0.26470 (18)0.0407 (7)
C50.9861 (3)0.41201 (18)0.13955 (17)0.0395 (7)
H51.02570.45420.11690.047*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0464 (2)0.0958 (3)0.03640 (18)0.00140 (18)0.00221 (14)0.01806 (17)
Zn10.02823 (17)0.03136 (17)0.03169 (17)0.00148 (12)0.00694 (12)0.00090 (12)
O10.0395 (11)0.0411 (11)0.0405 (11)0.0139 (9)0.0070 (9)0.0032 (9)
O50.0729 (17)0.104 (2)0.0352 (13)0.0491 (16)0.0079 (11)0.0015 (13)
O20.096 (2)0.105 (2)0.0442 (14)0.0616 (19)0.0100 (14)0.0226 (15)
O30.0710 (17)0.0769 (18)0.0415 (13)0.0371 (14)0.0045 (12)0.0003 (12)
O40.0594 (15)0.0634 (16)0.0567 (14)0.0345 (13)0.0024 (12)0.0088 (12)
N40.0306 (11)0.0326 (12)0.0361 (12)0.0019 (9)0.0041 (9)0.0000 (10)
N10.0401 (13)0.0330 (12)0.0347 (12)0.0028 (10)0.0113 (10)0.0012 (10)
N20.0433 (14)0.0361 (13)0.0420 (13)0.0032 (10)0.0186 (11)0.0006 (10)
N30.0274 (11)0.0378 (12)0.0348 (12)0.0036 (9)0.0050 (9)0.0010 (10)
C60.0344 (14)0.0494 (17)0.0292 (13)0.0018 (13)0.0037 (11)0.0030 (12)
C70.0285 (13)0.0424 (15)0.0359 (14)0.0053 (12)0.0031 (11)0.0048 (12)
C20.0335 (14)0.0376 (15)0.0324 (14)0.0070 (11)0.0080 (11)0.0033 (11)
C10.0394 (16)0.0433 (16)0.0366 (15)0.0113 (13)0.0072 (12)0.0002 (13)
C110.065 (2)0.0305 (15)0.0474 (17)0.0080 (14)0.0252 (16)0.0038 (13)
C120.074 (2)0.0314 (15)0.0526 (19)0.0008 (15)0.0320 (17)0.0045 (13)
C100.0381 (15)0.0347 (14)0.0354 (14)0.0029 (12)0.0107 (12)0.0014 (11)
C90.079 (3)0.0372 (17)0.068 (2)0.0083 (17)0.036 (2)0.0110 (16)
C130.0391 (15)0.0370 (15)0.0435 (16)0.0036 (12)0.0181 (13)0.0020 (13)
C180.0420 (17)0.0517 (19)0.0450 (17)0.0030 (14)0.0077 (14)0.0066 (14)
C170.0313 (15)0.0532 (19)0.0526 (18)0.0068 (13)0.0089 (13)0.0008 (15)
C160.0340 (14)0.0406 (16)0.0400 (15)0.0088 (12)0.0114 (12)0.0033 (12)
C150.0378 (15)0.0434 (16)0.0380 (15)0.0091 (13)0.0061 (12)0.0005 (13)
C140.0324 (14)0.0427 (16)0.0504 (17)0.0090 (13)0.0099 (13)0.0008 (14)
C190.0411 (16)0.0537 (19)0.0377 (16)0.0155 (14)0.0120 (13)0.0054 (14)
C200.0328 (14)0.0410 (15)0.0356 (14)0.0060 (12)0.0115 (11)0.0038 (12)
C250.0328 (14)0.0491 (17)0.0365 (15)0.0080 (12)0.0150 (12)0.0013 (13)
C240.0346 (14)0.0478 (17)0.0301 (14)0.0053 (12)0.0083 (11)0.0044 (12)
C230.0269 (13)0.0361 (14)0.0377 (14)0.0042 (11)0.0072 (11)0.0030 (12)
C220.0337 (14)0.0443 (16)0.0380 (15)0.0080 (12)0.0171 (12)0.0063 (12)
C210.0363 (15)0.0484 (17)0.0346 (14)0.0081 (13)0.0142 (12)0.0087 (12)
C280.0301 (14)0.0421 (16)0.0372 (15)0.0030 (12)0.0062 (11)0.0052 (12)
C290.0307 (14)0.0357 (14)0.0398 (15)0.0031 (11)0.0061 (12)0.0026 (12)
C270.0310 (13)0.0328 (14)0.0386 (15)0.0027 (11)0.0055 (11)0.0010 (11)
C260.053 (2)0.0451 (18)0.057 (2)0.0128 (15)0.0060 (16)0.0141 (15)
C30.0376 (15)0.0418 (15)0.0281 (13)0.0096 (12)0.0056 (11)0.0032 (11)
C40.0338 (14)0.0395 (15)0.0339 (14)0.0078 (12)0.0066 (11)0.0064 (12)
C80.0387 (16)0.0449 (17)0.0401 (16)0.0114 (13)0.0125 (13)0.0083 (13)
C50.0366 (15)0.0427 (16)0.0409 (16)0.0049 (12)0.0125 (13)0.0033 (13)
Geometric parameters (Å, º) top
Br1—C61.896 (3)C13—C181.376 (4)
Zn1—O4i1.923 (2)C13—C141.377 (4)
Zn1—O11.937 (2)C18—C171.384 (4)
Zn1—N12.001 (2)C18—H180.9300
Zn1—N4ii2.029 (2)C17—C161.384 (4)
O1—C11.272 (3)C17—H170.9300
O5—C191.206 (4)C16—C151.388 (4)
O2—C11.206 (4)C16—C191.498 (4)
O3—C81.224 (4)C15—C141.369 (4)
O4—C81.262 (4)C15—H150.9300
O4—Zn1iii1.923 (2)C14—H140.9300
N4—C271.324 (4)C19—C201.482 (4)
N4—C291.376 (4)C20—C211.378 (4)
N4—Zn1iv2.029 (2)C20—C251.396 (4)
N1—C101.315 (4)C25—C241.382 (4)
N1—C111.377 (4)C25—H250.9300
N2—C101.345 (4)C24—C231.375 (4)
N2—C121.376 (4)C24—H240.9300
N2—C131.432 (4)C23—C221.384 (4)
N3—C271.351 (4)C22—C211.375 (4)
N3—C281.381 (4)C22—H220.9300
N3—C231.420 (3)C21—H210.9300
C6—C71.370 (4)C28—C291.346 (4)
C6—C51.379 (4)C28—H280.9300
C7—C21.388 (4)C29—H290.9300
C7—H70.9300C27—C261.475 (4)
C2—C31.386 (4)C26—H26A0.9600
C2—C11.505 (4)C26—H26B0.9600
C11—C121.337 (4)C26—H26C0.9600
C11—H110.9300C3—C41.378 (4)
C12—H120.9300C3—H30.9300
C10—C91.479 (4)C4—C51.384 (4)
C9—H9A0.9600C4—C81.508 (4)
C9—H9B0.9600C5—H50.9300
C9—H9C0.9600
O4i—Zn1—O1116.87 (12)C17—C16—C19123.0 (3)
O4i—Zn1—N1100.70 (11)C15—C16—C19117.2 (3)
O1—Zn1—N1119.91 (9)C14—C15—C16119.9 (3)
O4i—Zn1—N4ii118.56 (10)C14—C15—H15120.0
O1—Zn1—N4ii96.63 (9)C16—C15—H15120.0
N1—Zn1—N4ii104.64 (10)C15—C14—C13119.6 (3)
C1—O1—Zn1118.68 (19)C15—C14—H14120.2
C8—O4—Zn1iii129.5 (2)C13—C14—H14120.2
C27—N4—C29106.3 (2)O5—C19—C20120.6 (3)
C27—N4—Zn1iv128.24 (19)O5—C19—C16119.7 (3)
C29—N4—Zn1iv124.89 (19)C20—C19—C16119.7 (3)
C10—N1—C11107.0 (2)C21—C20—C25119.0 (3)
C10—N1—Zn1129.37 (19)C21—C20—C19118.2 (3)
C11—N1—Zn1123.44 (19)C25—C20—C19122.7 (2)
C10—N2—C12108.1 (2)C24—C25—C20120.0 (3)
C10—N2—C13125.6 (2)C24—C25—H25120.0
C12—N2—C13125.6 (3)C20—C25—H25120.0
C27—N3—C28107.9 (2)C23—C24—C25119.8 (3)
C27—N3—C23126.6 (2)C23—C24—H24120.1
C28—N3—C23125.5 (2)C25—C24—H24120.1
C7—C6—C5122.0 (3)C24—C23—C22120.7 (3)
C7—C6—Br1118.7 (2)C24—C23—N3120.3 (2)
C5—C6—Br1119.3 (2)C22—C23—N3119.0 (2)
C6—C7—C2119.1 (3)C21—C22—C23119.1 (3)
C6—C7—H7120.4C21—C22—H22120.4
C2—C7—H7120.4C23—C22—H22120.4
C3—C2—C7119.1 (3)C22—C21—C20121.2 (3)
C3—C2—C1120.3 (3)C22—C21—H21119.4
C7—C2—C1120.6 (2)C20—C21—H21119.4
O2—C1—O1124.3 (3)C29—C28—N3105.7 (3)
O2—C1—C2120.2 (3)C29—C28—H28127.1
O1—C1—C2115.6 (3)N3—C28—H28127.1
C12—C11—N1109.2 (3)C28—C29—N4110.0 (3)
C12—C11—H11125.4C28—C29—H29125.0
N1—C11—H11125.4N4—C29—H29125.0
C11—C12—N2106.1 (3)N4—C27—N3110.0 (2)
C11—C12—H12126.9N4—C27—C26124.5 (3)
N2—C12—H12126.9N3—C27—C26125.3 (3)
N1—C10—N2109.5 (2)C27—C26—H26A109.5
N1—C10—C9126.6 (3)C27—C26—H26B109.5
N2—C10—C9123.9 (3)H26A—C26—H26B109.5
C10—C9—H9A109.5C27—C26—H26C109.5
C10—C9—H9B109.5H26A—C26—H26C109.5
H9A—C9—H9B109.5H26B—C26—H26C109.5
C10—C9—H9C109.5C4—C3—C2121.4 (3)
H9A—C9—H9C109.5C4—C3—H3119.3
H9B—C9—H9C109.5C2—C3—H3119.3
C18—C13—C14121.5 (3)C3—C4—C5119.3 (3)
C18—C13—N2120.5 (3)C3—C4—C8120.3 (3)
C14—C13—N2118.0 (3)C5—C4—C8120.4 (3)
C13—C18—C17118.7 (3)O3—C8—O4125.5 (3)
C13—C18—H18120.6O3—C8—C4120.0 (3)
C17—C18—H18120.6O4—C8—C4114.4 (3)
C18—C17—C16120.3 (3)C6—C5—C4119.1 (3)
C18—C17—H17119.9C6—C5—H5120.4
C16—C17—H17119.9C4—C5—H5120.4
C17—C16—C15119.8 (3)
C5—C6—C7—C20.1 (5)O5—C19—C20—C25152.2 (4)
Br1—C6—C7—C2179.0 (2)C16—C19—C20—C2526.2 (5)
C6—C7—C2—C30.7 (4)C21—C20—C25—C243.0 (5)
C6—C7—C2—C1178.0 (3)C19—C20—C25—C24179.9 (3)
Zn1—O1—C1—O213.0 (5)C20—C25—C24—C231.8 (5)
Zn1—O1—C1—C2166.58 (19)C25—C24—C23—C225.2 (5)
C3—C2—C1—O26.8 (5)C25—C24—C23—N3176.6 (3)
C7—C2—C1—O2175.9 (3)C27—N3—C23—C2445.0 (4)
C3—C2—C1—O1172.8 (3)C28—N3—C23—C24135.4 (3)
C7—C2—C1—O14.5 (4)C27—N3—C23—C22136.8 (3)
C10—N1—C11—C121.1 (4)C28—N3—C23—C2242.8 (4)
Zn1—N1—C11—C12174.4 (2)C24—C23—C22—C213.7 (5)
N1—C11—C12—N21.1 (4)N3—C23—C22—C21178.1 (3)
C10—N2—C12—C110.7 (4)C23—C22—C21—C201.3 (5)
C13—N2—C12—C11169.7 (3)C25—C20—C21—C224.5 (5)
C11—N1—C10—N20.6 (3)C19—C20—C21—C22178.2 (3)
Zn1—N1—C10—N2174.5 (2)C27—N3—C28—C291.3 (3)
C11—N1—C10—C9178.6 (3)C23—N3—C28—C29179.1 (3)
Zn1—N1—C10—C96.3 (5)N3—C28—C29—N40.6 (3)
C12—N2—C10—N10.0 (4)C27—N4—C29—C280.3 (3)
C13—N2—C10—N1170.4 (3)Zn1iv—N4—C29—C28171.8 (2)
C12—N2—C10—C9179.3 (3)C29—N4—C27—N31.1 (3)
C13—N2—C10—C98.9 (5)Zn1iv—N4—C27—N3170.65 (18)
C10—N2—C13—C1890.3 (4)C29—N4—C27—C26174.2 (3)
C12—N2—C13—C18101.0 (4)Zn1iv—N4—C27—C2614.0 (4)
C10—N2—C13—C1489.1 (4)C28—N3—C27—N41.5 (3)
C12—N2—C13—C1479.7 (4)C23—N3—C27—N4178.8 (2)
C14—C13—C18—C173.2 (5)C28—N3—C27—C26173.8 (3)
N2—C13—C18—C17176.2 (3)C23—N3—C27—C265.9 (5)
C13—C18—C17—C160.6 (5)C7—C2—C3—C40.8 (4)
C18—C17—C16—C152.9 (5)C1—C2—C3—C4178.1 (3)
C18—C17—C16—C19176.3 (3)C2—C3—C4—C50.0 (5)
C17—C16—C15—C144.0 (5)C2—C3—C4—C8179.6 (3)
C19—C16—C15—C14175.3 (3)Zn1iii—O4—C8—O33.7 (6)
C16—C15—C14—C131.5 (5)Zn1iii—O4—C8—C4177.2 (2)
C18—C13—C14—C152.1 (5)C3—C4—C8—O36.8 (5)
N2—C13—C14—C15177.2 (3)C5—C4—C8—O3172.7 (3)
C17—C16—C19—O5153.0 (4)C3—C4—C8—O4173.9 (3)
C15—C16—C19—O527.8 (5)C5—C4—C8—O46.5 (4)
C17—C16—C19—C2028.7 (5)C7—C6—C5—C40.9 (5)
C15—C16—C19—C20150.5 (3)Br1—C6—C5—C4178.2 (2)
O5—C19—C20—C2125.0 (5)C3—C4—C5—C60.8 (4)
C16—C19—C20—C21156.6 (3)C8—C4—C5—C6178.8 (3)
Symmetry codes: (i) x+2, y1/2, z+1/2; (ii) x, y1/2, z+1/2; (iii) x+2, y+1/2, z+1/2; (iv) x, y+1/2, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C9—H9C···O5v0.962.493.427 (5)164
C28—H28···O3vi0.932.363.248 (4)159
Symmetry codes: (v) x, y+1/2, z1/2; (vi) x+1, y+1, z+1.
 

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