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A novel hydrolytic stable CoII–organic framework, namely poly[[bis­(2-amino-4-sulfonato­benzoato-κO1)tetra­aqua­tris­{μ-1,4-bis­[(imidazol-1-yl)meth­yl]benzene-κ2N3:N3′}dicobalt(II)] tetra­hydrate], {[Co(C7H5NO5S)(C14H14N4)1.5(H2O)2]·2H2O}n, (1), based on multifunctional 2-amino-5-sulfo­benzoic acid (H2asba) and the auxiliary flexible ligand 1,4-bis­[(imidazol-1-yl)meth­yl]benzene (bix), was prepared using the solution evaporation method. The purity of (1) was confirmed by elemental analysis and powder X-ray diffraction (PXRD) analysis. Complex (1) shows a novel 1D→2D inter­penetrating network, which is further extended into a 3D supra­molecular framework with channels occupied by the lattice water mol­ecules. The 2-amino-4-sulfonato­benzoate (asba2−) ligand adopts a monodentate coordination mode. The bix ligands exhibit gauche–gauche (GG) and trans–trans (TT) conformations. A detailed analysis of the solid-state diffuse-reflectance UV–Vis spectrum reveals that an indirect band gap exists in the com­plex. The band structure, the total density of states (TDOS) and the partial density of states (PDOS) were calculated using the CASTEP program. The calculated band gap (Eg) matches well with the experimental one. The com­plex exhibits a reversible dehydration–rehydration behaviour. Inter­estingly, gas sorption experiments demonstrate that the new fully anhydrous com­pound obtained by activating com­plex (1) at 400 K shows selective adsorption of CO2 over N2. Complex (1) retains excellent framework stability in a variety of solvents and manifests distinct solvent-dependent fluorescence properties. Moreover, the com­plex shows multiresponsive fluorescence sensing for some nitro­aromatics in aqueous medium.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229619014669/yf3197sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229619014669/yf3197Isup2.hkl
Contains datablock I

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2053229619014669/yf3197sup3.pdf
Additional figures and spectra

CCDC reference: 1482482

Computing details top

Data collection: SMART (Bruker, 2008); cell refinement: SMART (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXL2016 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: Mercury (Macrae et al., 2008).

Poly[[bis(2-amino-4-sulfonatobenzoato-κO1)tetraaquatris{µ-1,4-bis[(imidazol-1-yl)methyl]benzene-κ2N3:N3'}dicobalt(II)] tetrahydrate] top
Crystal data top
[Co(C7H5NO5S)(C14H14N4)1.5(H2O)2]·2H2OF(000) = 1464
Mr = 703.62Dx = 1.499 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 10.8248 (10) ÅCell parameters from 9911 reflections
b = 21.331 (2) Åθ = 2.4–27.5°
c = 13.5460 (15) ŵ = 0.68 mm1
β = 94.595 (3)°T = 296 K
V = 3117.8 (5) Å3Block, purple
Z = 40.25 × 0.2 × 0.18 mm
Data collection top
Bruker SMART CCD area detector
diffractometer
5163 reflections with I > 2σ(I)
phi and ω scansRint = 0.048
Absorption correction: empirical (using intensity measurements)
(SADABS; Bruker, 2008)
θmax = 27.6°, θmin = 1.8°
Tmin = 0.849, Tmax = 0.930h = 1413
47170 measured reflectionsk = 2127
7197 independent reflectionsl = 1717
Refinement top
Refinement on F212 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.040H-atom parameters constrained
wR(F2) = 0.093 w = 1/[σ2(Fo2) + (0.0388P)2 + 1.5321P]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max < 0.001
7197 reflectionsΔρmax = 0.43 e Å3
415 parametersΔρmin = 0.24 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
C10.55205 (19)0.73516 (10)0.11040 (15)0.0303 (5)
C20.48663 (18)0.68925 (9)0.05218 (15)0.0280 (5)
C30.54735 (18)0.65821 (10)0.02082 (15)0.0296 (5)
H30.5048780.6277550.0591510.036*
C40.66839 (18)0.67152 (10)0.03753 (15)0.0290 (5)
C50.73010 (19)0.71917 (10)0.01588 (16)0.0340 (5)
H50.8105560.7297630.0029050.041*
C60.67307 (19)0.75057 (11)0.08742 (17)0.0361 (5)
H60.7150800.7828840.1217920.043*
C70.35682 (19)0.66993 (10)0.06816 (16)0.0318 (5)
C80.0135 (2)0.80637 (11)0.16561 (17)0.0382 (5)
H80.0533460.7880120.1290820.046*
C90.1331 (2)0.87657 (11)0.23801 (18)0.0425 (6)
H90.1662180.9145330.2612200.051*
C100.1840 (2)0.81947 (10)0.25198 (17)0.0373 (5)
H100.2593070.8114590.2877790.045*
C110.0705 (2)0.91532 (12)0.1536 (2)0.0477 (6)
H11A0.0876000.9397930.2112640.057*
H11B0.1466700.8944310.1295790.057*
C120.03121 (19)0.95894 (10)0.07418 (16)0.0329 (5)
C130.0063 (2)0.93627 (10)0.01424 (17)0.0364 (5)
H130.0109810.8932350.0242360.044*
C140.03677 (19)1.02317 (10)0.08777 (16)0.0353 (5)
H140.0612971.0391230.1470380.042*
C150.3156 (2)0.63290 (10)0.35967 (16)0.0370 (5)
H150.3517470.6072460.3145120.044*
C160.2797 (2)0.67932 (10)0.49662 (16)0.0378 (5)
H160.2842820.6921980.5624050.045*
C170.1961 (2)0.69774 (10)0.42368 (16)0.0364 (5)
H170.1324990.7262480.4309930.044*
C180.4639 (2)0.60589 (11)0.50453 (17)0.0395 (5)
H18A0.5179810.6367680.5381290.047*
H18B0.5099200.5854650.4550370.047*
C190.42871 (19)0.55762 (10)0.57882 (16)0.0319 (5)
C200.3270 (2)0.51942 (11)0.56079 (17)0.0405 (6)
H200.2756890.5248120.5029980.049*
C210.29972 (19)0.47301 (11)0.62737 (18)0.0396 (6)
H210.2305390.4476780.6137120.048*
C220.37388 (19)0.46413 (10)0.71323 (16)0.0310 (5)
C230.4757 (2)0.50303 (11)0.73165 (17)0.0419 (6)
H230.5267840.4978080.7895860.050*
C240.5025 (2)0.54926 (11)0.66578 (17)0.0415 (6)
H240.5709330.5750560.6799380.050*
C250.1335 (2)0.61945 (10)0.19766 (17)0.0361 (5)
H250.1162810.5892980.1511090.043*
C260.2320 (2)0.67400 (11)0.30109 (18)0.0422 (6)
H260.2930990.6890850.3394010.051*
C270.1165 (2)0.69655 (11)0.29819 (17)0.0384 (5)
H270.0840140.7304020.3349570.046*
C280.3519 (2)0.41377 (11)0.78747 (18)0.0418 (6)
H28A0.4240280.3866380.7940300.050*
H28B0.3441830.4333420.8513140.050*
Co10.13043 (2)0.67662 (2)0.19342 (2)0.02851 (9)
N10.10881 (16)0.77464 (8)0.20574 (13)0.0324 (4)
N20.02332 (17)0.86780 (8)0.18304 (14)0.0370 (4)
N30.21837 (16)0.66843 (8)0.33721 (13)0.0328 (4)
N40.35656 (16)0.63793 (8)0.45495 (13)0.0328 (4)
N50.05354 (16)0.66210 (8)0.23279 (14)0.0348 (4)
N60.24231 (16)0.62477 (8)0.23702 (14)0.0357 (4)
N70.50401 (17)0.76515 (9)0.18705 (14)0.0456 (5)
H7A0.5472820.7928680.2204170.055*
H7B0.4303220.7564080.2022250.055*
O10.30963 (13)0.69040 (7)0.14428 (11)0.0377 (4)
O20.30064 (15)0.63448 (8)0.00598 (14)0.0543 (5)
O30.69991 (16)0.56416 (8)0.12086 (13)0.0515 (4)
O40.71524 (16)0.65599 (8)0.22058 (12)0.0509 (4)
O50.87662 (14)0.63194 (9)0.09371 (14)0.0583 (5)
O1W0.16273 (15)0.57782 (8)0.17163 (13)0.0493 (4)
H1WA0.1073380.5502320.1591240.074*
H1WB0.2147610.5767710.1286310.074*
O2W0.06616 (14)0.67859 (8)0.03544 (11)0.0429 (4)
H2WB0.0026390.6624950.0036860.064*
H2WA0.1304560.6634750.0123290.064*
O3W0.24633 (19)0.98955 (9)0.45318 (15)0.0716 (6)
H3WB0.2717980.9516320.4642020.107*
H3WA0.2749411.0111540.5042850.107*
O4W0.00112 (18)0.98599 (8)0.37977 (16)0.0661 (5)
H4WB0.0411260.9554650.3995660.099*
H4WA0.0722920.9856440.4120030.099*
S10.74575 (5)0.62794 (3)0.12506 (4)0.03206 (13)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0277 (11)0.0332 (12)0.0302 (11)0.0015 (9)0.0020 (9)0.0001 (9)
C20.0248 (10)0.0314 (11)0.0277 (11)0.0017 (8)0.0013 (8)0.0031 (9)
C30.0246 (10)0.0335 (11)0.0301 (11)0.0008 (9)0.0016 (9)0.0006 (9)
C40.0264 (10)0.0348 (12)0.0258 (11)0.0010 (9)0.0026 (8)0.0013 (9)
C50.0231 (10)0.0410 (13)0.0380 (12)0.0034 (9)0.0034 (9)0.0005 (10)
C60.0275 (11)0.0388 (12)0.0419 (13)0.0061 (9)0.0025 (9)0.0084 (10)
C70.0261 (11)0.0341 (12)0.0352 (12)0.0002 (9)0.0020 (9)0.0019 (10)
C80.0344 (12)0.0371 (13)0.0423 (14)0.0056 (10)0.0022 (10)0.0085 (10)
C90.0475 (14)0.0309 (13)0.0487 (15)0.0027 (10)0.0010 (12)0.0014 (11)
C100.0347 (12)0.0377 (13)0.0387 (13)0.0001 (10)0.0011 (10)0.0029 (10)
C110.0422 (14)0.0455 (14)0.0570 (16)0.0124 (11)0.0133 (12)0.0213 (12)
C120.0277 (11)0.0314 (12)0.0392 (13)0.0057 (9)0.0000 (9)0.0099 (10)
C130.0386 (12)0.0244 (11)0.0459 (14)0.0037 (9)0.0022 (10)0.0011 (10)
C140.0350 (12)0.0387 (13)0.0319 (12)0.0060 (10)0.0013 (9)0.0007 (10)
C150.0490 (14)0.0353 (12)0.0277 (12)0.0089 (10)0.0093 (10)0.0004 (10)
C160.0490 (14)0.0376 (13)0.0275 (12)0.0034 (11)0.0069 (10)0.0035 (10)
C170.0427 (13)0.0331 (12)0.0344 (13)0.0067 (10)0.0095 (10)0.0020 (10)
C180.0359 (12)0.0403 (13)0.0417 (13)0.0028 (10)0.0008 (10)0.0096 (11)
C190.0303 (11)0.0305 (11)0.0343 (12)0.0010 (9)0.0002 (9)0.0046 (9)
C200.0307 (12)0.0450 (14)0.0434 (14)0.0015 (10)0.0123 (10)0.0107 (11)
C210.0239 (11)0.0401 (13)0.0533 (15)0.0078 (10)0.0068 (10)0.0075 (11)
C220.0265 (11)0.0328 (12)0.0337 (12)0.0006 (9)0.0032 (9)0.0035 (9)
C230.0439 (14)0.0453 (14)0.0339 (13)0.0105 (11)0.0131 (10)0.0080 (11)
C240.0403 (13)0.0404 (13)0.0419 (14)0.0153 (11)0.0089 (11)0.0042 (11)
C250.0375 (13)0.0307 (12)0.0418 (13)0.0006 (10)0.0130 (10)0.0011 (10)
C260.0414 (13)0.0427 (14)0.0448 (14)0.0027 (11)0.0182 (11)0.0027 (11)
C270.0417 (14)0.0339 (12)0.0411 (13)0.0033 (10)0.0125 (11)0.0047 (10)
C280.0360 (13)0.0462 (14)0.0427 (14)0.0066 (10)0.0013 (10)0.0121 (11)
Co10.02796 (16)0.02889 (16)0.02914 (16)0.00229 (12)0.00506 (11)0.00235 (12)
N10.0335 (10)0.0298 (10)0.0337 (10)0.0019 (8)0.0013 (8)0.0067 (8)
N20.0368 (11)0.0316 (10)0.0429 (11)0.0031 (8)0.0057 (9)0.0129 (8)
N30.0397 (10)0.0328 (10)0.0263 (9)0.0067 (8)0.0058 (8)0.0026 (8)
N40.0389 (10)0.0305 (10)0.0290 (10)0.0026 (8)0.0025 (8)0.0047 (8)
N50.0333 (10)0.0322 (10)0.0403 (11)0.0011 (8)0.0121 (8)0.0012 (8)
N60.0330 (10)0.0341 (10)0.0410 (11)0.0046 (8)0.0105 (8)0.0053 (9)
N70.0333 (10)0.0582 (13)0.0463 (12)0.0101 (9)0.0100 (9)0.0223 (10)
O10.0280 (8)0.0551 (10)0.0309 (8)0.0099 (7)0.0071 (6)0.0019 (7)
O20.0339 (9)0.0630 (12)0.0675 (12)0.0162 (8)0.0131 (8)0.0316 (10)
O30.0603 (11)0.0376 (10)0.0570 (11)0.0012 (8)0.0075 (9)0.0081 (8)
O40.0574 (11)0.0639 (11)0.0324 (9)0.0134 (9)0.0095 (8)0.0045 (8)
O50.0243 (8)0.0834 (14)0.0662 (12)0.0087 (8)0.0036 (8)0.0351 (10)
O1W0.0489 (10)0.0413 (10)0.0588 (11)0.0005 (8)0.0118 (8)0.0143 (8)
O2W0.0295 (8)0.0638 (11)0.0352 (9)0.0073 (7)0.0006 (7)0.0076 (8)
O3W0.0850 (15)0.0585 (12)0.0701 (14)0.0075 (11)0.0020 (11)0.0041 (10)
O4W0.0618 (12)0.0419 (10)0.0942 (15)0.0028 (9)0.0038 (11)0.0116 (10)
S10.0249 (3)0.0400 (3)0.0310 (3)0.0041 (2)0.0006 (2)0.0046 (2)
Geometric parameters (Å, º) top
C1—N71.358 (3)C18—H18B0.9700
C1—C61.409 (3)C19—C201.376 (3)
C1—C21.412 (3)C19—C241.381 (3)
C2—C31.397 (3)C20—C211.387 (3)
C2—C71.497 (3)C20—H200.9300
C3—C41.377 (3)C21—C221.372 (3)
C3—H30.9300C21—H210.9300
C4—C51.388 (3)C22—C231.386 (3)
C4—S11.769 (2)C22—C281.503 (3)
C5—C61.365 (3)C23—C241.376 (3)
C5—H50.9300C23—H230.9300
C6—H60.9300C24—H240.9300
C7—O21.253 (3)C25—N51.318 (3)
C7—O11.265 (3)C25—N61.336 (3)
C8—N11.314 (3)C25—H250.9300
C8—N21.334 (3)C26—C271.344 (3)
C8—H80.9300C26—N61.361 (3)
C9—C101.344 (3)C26—H260.9300
C9—N21.364 (3)C27—N51.373 (3)
C9—H90.9300C27—H270.9300
C10—N11.374 (3)C28—N6ii1.460 (3)
C10—H100.9300C28—H28A0.9700
C11—N21.467 (3)C28—H28B0.9700
C11—C121.509 (3)Co1—N32.1056 (17)
C11—H11A0.9700Co1—N12.1121 (18)
C11—H11B0.9700Co1—O12.1211 (14)
C12—C131.382 (3)Co1—N52.1251 (17)
C12—C141.384 (3)Co1—O1W2.1605 (16)
C13—C14i1.379 (3)Co1—O2W2.1969 (15)
C13—H130.9300N7—H7A0.8599
C14—H140.9300N7—H7B0.8600
C15—N31.313 (3)O3—S11.4510 (17)
C15—N41.335 (3)O4—S11.4396 (17)
C15—H150.9300O5—S11.4485 (16)
C16—C171.344 (3)O1W—H1WA0.8474
C16—N41.366 (3)O1W—H1WB0.8424
C16—H160.9300O2W—H2WB0.8535
C17—N31.366 (3)O2W—H2WA0.8493
C17—H170.9300O3W—H3WB0.8636
C18—N41.464 (3)O3W—H3WA0.8679
C18—C191.510 (3)O4W—H4WB0.8513
C18—H18A0.9700O4W—H4WA0.8546
N7—C1—C6118.60 (19)C24—C23—C22121.2 (2)
N7—C1—C2123.25 (19)C24—C23—H23119.4
C6—C1—C2118.15 (19)C22—C23—H23119.4
C3—C2—C1118.73 (18)C23—C24—C19120.5 (2)
C3—C2—C7118.18 (18)C23—C24—H24119.7
C1—C2—C7123.02 (19)C19—C24—H24119.7
C4—C3—C2121.77 (19)N5—C25—N6111.8 (2)
C4—C3—H3119.1N5—C25—H25124.1
C2—C3—H3119.1N6—C25—H25124.1
C3—C4—C5119.34 (19)C27—C26—N6106.6 (2)
C3—C4—S1120.64 (16)C27—C26—H26126.7
C5—C4—S1120.02 (15)N6—C26—H26126.7
C6—C5—C4120.21 (19)C26—C27—N5109.8 (2)
C6—C5—H5119.9C26—C27—H27125.1
C4—C5—H5119.9N5—C27—H27125.1
C5—C6—C1121.6 (2)N6ii—C28—C22114.81 (18)
C5—C6—H6119.2N6ii—C28—H28A108.6
C1—C6—H6119.2C22—C28—H28A108.6
O2—C7—O1123.41 (19)N6ii—C28—H28B108.6
O2—C7—C2118.67 (19)C22—C28—H28B108.6
O1—C7—C2117.91 (19)H28A—C28—H28B107.5
N1—C8—N2112.6 (2)N3—Co1—N193.08 (7)
N1—C8—H8123.7N3—Co1—O186.83 (6)
N2—C8—H8123.7N1—Co1—O189.86 (6)
C10—C9—N2106.4 (2)N3—Co1—N596.84 (7)
C10—C9—H9126.8N1—Co1—N590.71 (7)
N2—C9—H9126.8O1—Co1—N5176.25 (6)
C9—C10—N1110.2 (2)N3—Co1—O1W88.81 (7)
C9—C10—H10124.9N1—Co1—O1W175.35 (7)
N1—C10—H10124.9O1—Co1—O1W86.00 (6)
N2—C11—C12113.05 (18)N5—Co1—O1W93.28 (7)
N2—C11—H11A109.0N3—Co1—O2W170.77 (6)
C12—C11—H11A109.0N1—Co1—O2W91.70 (6)
N2—C11—H11B109.0O1—Co1—O2W85.29 (6)
C12—C11—H11B109.0N5—Co1—O2W90.99 (6)
H11A—C11—H11B107.8O1W—Co1—O2W85.86 (6)
C13—C12—C14118.7 (2)C8—N1—C10104.30 (18)
C13—C12—C11121.4 (2)C8—N1—Co1124.42 (15)
C14—C12—C11119.9 (2)C10—N1—Co1131.27 (14)
C14i—C13—C12120.7 (2)C8—N2—C9106.54 (18)
C14i—C13—H13119.7C8—N2—C11125.9 (2)
C12—C13—H13119.7C9—N2—C11127.4 (2)
C13i—C14—C12120.6 (2)C15—N3—C17104.99 (18)
C13i—C14—H14119.7C15—N3—Co1123.84 (14)
C12—C14—H14119.7C17—N3—Co1131.11 (15)
N3—C15—N4112.06 (19)C15—N4—C16106.59 (18)
N3—C15—H15124.0C15—N4—C18126.57 (19)
N4—C15—H15124.0C16—N4—C18126.84 (19)
C17—C16—N4106.35 (19)C25—N5—C27104.88 (18)
C17—C16—H16126.8C25—N5—Co1127.70 (15)
N4—C16—H16126.8C27—N5—Co1127.39 (15)
C16—C17—N3110.0 (2)C25—N6—C26106.88 (18)
C16—C17—H17125.0C25—N6—C28ii126.0 (2)
N3—C17—H17125.0C26—N6—C28ii127.07 (19)
N4—C18—C19113.00 (18)C1—N7—H7A120.0
N4—C18—H18A109.0C1—N7—H7B120.0
C19—C18—H18A109.0H7A—N7—H7B120.0
N4—C18—H18B109.0C7—O1—Co1130.34 (13)
C19—C18—H18B109.0Co1—O1W—H1WA125.8
H18A—C18—H18B107.8Co1—O1W—H1WB104.2
C20—C19—C24118.4 (2)H1WA—O1W—H1WB110.2
C20—C19—C18121.78 (19)Co1—O2W—H2WB131.5
C24—C19—C18119.80 (19)Co1—O2W—H2WA98.4
C19—C20—C21121.1 (2)H2WB—O2W—H2WA108.2
C19—C20—H20119.5H3WB—O3W—H3WA105.7
C21—C20—H20119.5H4WB—O4W—H4WA108.5
C22—C21—C20120.6 (2)O4—S1—O5112.80 (11)
C22—C21—H21119.7O4—S1—O3111.74 (11)
C20—C21—H21119.7O5—S1—O3111.92 (11)
C21—C22—C23118.2 (2)O4—S1—C4107.29 (10)
C21—C22—C28123.54 (19)O5—S1—C4106.07 (10)
C23—C22—C28118.26 (19)O3—S1—C4106.53 (10)
N7—C1—C2—C3175.8 (2)C21—C22—C28—N6ii1.6 (3)
C6—C1—C2—C34.3 (3)C23—C22—C28—N6ii179.5 (2)
N7—C1—C2—C71.1 (3)N2—C8—N1—C100.1 (3)
C6—C1—C2—C7178.74 (19)N2—C8—N1—Co1178.93 (14)
C1—C2—C3—C40.4 (3)C9—C10—N1—C80.5 (3)
C7—C2—C3—C4177.46 (19)C9—C10—N1—Co1178.44 (16)
C2—C3—C4—C53.3 (3)N1—C8—N2—C90.3 (3)
C2—C3—C4—S1175.94 (16)N1—C8—N2—C11176.2 (2)
C3—C4—C5—C63.0 (3)C10—C9—N2—C80.6 (3)
S1—C4—C5—C6176.32 (17)C10—C9—N2—C11175.8 (2)
C4—C5—C6—C11.1 (3)C12—C11—N2—C8111.5 (3)
N7—C1—C6—C5175.4 (2)C12—C11—N2—C972.8 (3)
C2—C1—C6—C54.8 (3)N4—C15—N3—C170.1 (3)
C3—C2—C7—O211.4 (3)N4—C15—N3—Co1177.47 (14)
C1—C2—C7—O2171.6 (2)C16—C17—N3—C150.2 (3)
C3—C2—C7—O1168.48 (19)C16—C17—N3—Co1177.54 (15)
C1—C2—C7—O18.5 (3)N3—C15—N4—C160.4 (3)
N2—C9—C10—N10.7 (3)N3—C15—N4—C18178.90 (19)
N2—C11—C12—C1354.6 (3)C17—C16—N4—C150.5 (2)
N2—C11—C12—C14127.8 (2)C17—C16—N4—C18178.8 (2)
C14—C12—C13—C14i0.4 (4)C19—C18—N4—C15111.8 (2)
C11—C12—C13—C14i177.2 (2)C19—C18—N4—C1669.0 (3)
C13—C12—C14—C13i0.4 (4)N6—C25—N5—C270.2 (3)
C11—C12—C14—C13i177.2 (2)N6—C25—N5—Co1178.30 (14)
N4—C16—C17—N30.4 (3)C26—C27—N5—C250.1 (3)
N4—C18—C19—C2039.3 (3)C26—C27—N5—Co1178.17 (15)
N4—C18—C19—C24143.4 (2)N5—C25—N6—C260.3 (3)
C24—C19—C20—C210.9 (4)N5—C25—N6—C28ii178.23 (19)
C18—C19—C20—C21176.5 (2)C27—C26—N6—C250.2 (3)
C19—C20—C21—C220.1 (4)C27—C26—N6—C28ii178.1 (2)
C20—C21—C22—C230.5 (3)O2—C7—O1—Co11.5 (3)
C20—C21—C22—C28178.4 (2)C2—C7—O1—Co1178.62 (13)
C21—C22—C23—C240.3 (4)C3—C4—S1—O485.05 (19)
C28—C22—C23—C24178.7 (2)C5—C4—S1—O495.66 (19)
C22—C23—C24—C190.6 (4)C3—C4—S1—O5154.15 (18)
C20—C19—C24—C231.1 (4)C5—C4—S1—O525.1 (2)
C18—C19—C24—C23176.3 (2)C3—C4—S1—O334.8 (2)
N6—C26—C27—N50.1 (3)C5—C4—S1—O3144.53 (18)
Symmetry codes: (i) x, y+2, z; (ii) x, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4W—H4WB···O5iii0.852.072.890 (3)161
C23—H23···O3iv0.932.573.287 (3)134
C21—H21···N6ii0.932.542.880 (3)102
O3W—H3WA···O3v0.871.942.796 (3)167
C28—H28B···O3Wvi0.972.443.318 (3)150
C6—H6···O4vi0.932.503.280 (3)141
N7—H7A···O4vi0.862.213.027 (3)158
O3W—H3WB···O2vi0.861.942.791 (3)168
O2W—H2WB···O5vii0.851.932.772 (2)167
C25—H25···O4Wviii0.932.583.391 (3)146
O1W—H1WA···O4Wviii0.851.852.696 (2)173
Symmetry codes: (ii) x, y+1, z+1; (iii) x1, y+3/2, z+1/2; (iv) x, y, z+1; (v) x+1, y+1/2, z+1/2; (vi) x, y+3/2, z+1/2; (vii) x1, y, z; (viii) x, y1/2, z+1/2.
The fluorescence quenching percentage (QP) (0.075 mM), Stern–Volmer constants (KSV) and the limits of detection (LOD) for some NACs top
NACsQP (%)KSV (l mol-1)LOD (ppm)
2-MO-5-NP46.351.15 × 1041.38
TNP78.294.81 × 1040.37
4-NA77.074.48 × 1040.64
2-M-4-NA79.505.17 × 1040.57
2,6-DC-4-NP63.562.33 × 1040.89
 

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