Download citation
Download citation
link to html
Compared with the monomorphic type of ligand, combining mixed ligands in one coordination polymer offers greater tunability of the structural framework. Employment of N-heterocyclic ligands and aromatic polycarboxyl­ates is an effective approach for the construction of metal–organic frameworks (MOFs). Two new coordination polymers incorporating both 2-[(1H-imidazol-1-yl)meth­yl]-1H-benzimidazole (imb) and benzene­dicarb­oxy­lic acid isomers, namely, catena-poly[[[di-μ-chlorido-­bis­[(2-carb­oxy­benzoato-κ2O1,O1′)cadmium(II)]]-bis­{μ-2-[(1H-imidazol-1-yl)meth­yl]-1H-benzimidazole-κ2N:N′}] dihydrate], {[Cd(C8H5O4)Cl(C11H10N4)]·H2O}n, (I), and poly[[aqua(μ2-benzene-1,3-di­carboxyl­ato-κ3O1,O1′:O3)­{μ2-2-[(1H-imidazol-1-yl)meth­yl]-1H-benzimidazole-κ2N:N′}cadmium(II)] dihydrate], {[Cd(C8H4O4)(C11H10N4)(H2O)]·2H2O}n, (II), have been prepared and structurally characterized by single-crystal X-ray diffraction. In polymer (I), imb ligands bridge CdII ions, forming a one-dimensional chain, and 2-carb­oxy­benzoate anions coordinate to the CdII ions in a terminal fashion. Polymer (II) exhibits a two-dimensional network structure in which imb ligands and the benzene-1,3-di­carboxyl­ate anions join CdII ions co-operatively. This indicates that changing of the aromatic di­carb­oxy­lic acids can result in polymers with different compositions and architectures. Moreover, their IR spectra, PXRD (powder X-ray diffraction) patterns, thermogravimetric analyses and fluorescence properties were also investigated.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229619005758/lg3237sup1.cif
Contains datablocks global, I, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229619005758/lg3237Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229619005758/lg3237IIsup3.hkl
Contains datablock II

CCDC references: 1036799; 1036798

Computing details top

For both structures, 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).

catena-Poly[[[di-µ-chlorido-bis[(2-carboxybenzoato-κ2O1,O1')cadmium(II)]]-bis{µ-2-[(1H-imidazol-1-yl)methyl]-1H-benzimidazole-κ2N:N'}] dihydrate] (I) top
Crystal data top
[Cd(C8H5O4)Cl(C11H10N4)]·H2OZ = 2
Mr = 529.21F(000) = 528
Triclinic, P1Dx = 1.783 Mg m3
a = 8.5888 (17) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.372 (2) ÅCell parameters from 3326 reflections
c = 11.660 (2) Åθ = 2.0–27.9°
α = 64.87 (3)°µ = 1.28 mm1
β = 73.10 (3)°T = 293 K
γ = 80.71 (3)°Prism, colourless
V = 985.6 (4) Å30.19 × 0.18 × 0.16 mm
Data collection top
Rigaku Saturn
diffractometer
4646 independent reflections
Radiation source: fine-focus sealed tube4153 reflections with I > 2σ(I)
Detector resolution: 28.5714 pixels mm-1Rint = 0.026
ω scansθmax = 27.9°, θmin = 2.0°
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2004)
h = 1111
Tmin = 0.925, Tmax = 1.000k = 1414
9602 measured reflectionsl = 1515
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: mixed
wR(F2) = 0.075H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0257P)2 + 0.7865P]
where P = (Fo2 + 2Fc2)/3
4646 reflections(Δ/σ)max = 0.001
262 parametersΔρmax = 0.57 e Å3
0 restraintsΔρmin = 0.40 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
Cd10.34122 (3)0.14547 (2)0.48348 (2)0.03004 (8)
Cl10.54477 (10)0.00851 (8)0.63219 (8)0.03943 (19)
O10.1237 (3)0.0356 (2)0.6555 (2)0.0474 (6)
O20.1733 (3)0.2101 (2)0.6645 (2)0.0482 (6)
O30.0762 (3)0.3390 (2)0.7952 (3)0.0565 (7)
H3A0.10840.29660.75020.085*
O40.1104 (4)0.3310 (3)0.9692 (3)0.0777 (10)
N10.1430 (3)0.2317 (3)0.3688 (3)0.0360 (6)
N20.0788 (3)0.2614 (2)0.3014 (3)0.0318 (6)
N30.4796 (3)0.3310 (2)0.3800 (2)0.0277 (5)
N40.6742 (3)0.4721 (2)0.2934 (3)0.0344 (6)
H4A0.76990.50260.25840.041*
C10.0945 (3)0.1115 (3)0.7061 (3)0.0293 (6)
C20.0521 (4)0.0855 (3)0.8279 (3)0.0340 (7)
C30.1337 (4)0.0267 (3)0.8619 (4)0.0444 (8)
H30.09650.07550.81160.053*
C40.2654 (4)0.0666 (4)0.9661 (4)0.0517 (9)
H40.31730.14090.98550.062*
C50.3208 (5)0.0036 (4)1.0423 (4)0.0535 (10)
H50.40930.02401.11440.064*
C60.2458 (4)0.1143 (4)1.0121 (4)0.0470 (9)
H60.28550.16151.06390.056*
C70.1106 (4)0.1586 (3)0.9051 (3)0.0371 (7)
C80.0461 (5)0.2836 (4)0.8905 (4)0.0465 (8)
C90.0078 (3)0.1976 (3)0.4000 (3)0.0317 (7)
H90.05860.13640.48080.038*
C100.1686 (4)0.3217 (4)0.2434 (4)0.0541 (10)
H100.26540.36360.19460.065*
C110.0338 (4)0.3416 (4)0.2002 (4)0.0504 (9)
H110.01990.39830.11800.061*
C120.2443 (3)0.2474 (3)0.3006 (3)0.0358 (7)
H12A0.28040.16260.36580.043*
H12B0.24310.25070.21580.043*
C130.6363 (3)0.3491 (3)0.3275 (3)0.0292 (6)
C140.5314 (4)0.5404 (3)0.3248 (3)0.0310 (6)
C150.4999 (4)0.6688 (3)0.3110 (4)0.0405 (8)
H150.58270.72710.27560.049*
C160.3404 (4)0.7053 (3)0.3520 (4)0.0437 (8)
H160.31440.79030.34490.052*
C170.2164 (4)0.6180 (3)0.4042 (4)0.0431 (8)
H170.10930.64650.42960.052*
C180.2488 (4)0.4904 (3)0.4190 (3)0.0389 (8)
H180.16590.43220.45500.047*
C190.4101 (3)0.4518 (3)0.3780 (3)0.0295 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cd10.02381 (11)0.02566 (12)0.03979 (14)0.00180 (8)0.00474 (9)0.01410 (10)
Cl10.0453 (4)0.0392 (4)0.0426 (5)0.0095 (3)0.0175 (4)0.0243 (4)
O10.0409 (13)0.0453 (14)0.0495 (15)0.0054 (11)0.0018 (11)0.0201 (12)
O20.0377 (13)0.0488 (14)0.0527 (16)0.0094 (11)0.0022 (11)0.0215 (12)
O30.0519 (16)0.0534 (15)0.0672 (18)0.0220 (12)0.0070 (14)0.0342 (14)
O40.104 (3)0.072 (2)0.068 (2)0.0217 (18)0.0062 (18)0.0491 (18)
N10.0253 (13)0.0406 (15)0.0434 (16)0.0021 (11)0.0081 (12)0.0179 (13)
N20.0225 (12)0.0301 (13)0.0448 (16)0.0008 (10)0.0074 (11)0.0181 (12)
N30.0239 (12)0.0211 (11)0.0376 (14)0.0023 (9)0.0095 (10)0.0095 (11)
N40.0241 (12)0.0281 (13)0.0499 (17)0.0054 (10)0.0081 (12)0.0139 (12)
C10.0259 (14)0.0237 (14)0.0370 (17)0.0023 (11)0.0127 (13)0.0089 (13)
C20.0312 (16)0.0343 (16)0.0345 (17)0.0015 (13)0.0094 (13)0.0121 (14)
C30.0403 (19)0.0439 (19)0.049 (2)0.0070 (15)0.0063 (16)0.0203 (17)
C40.046 (2)0.048 (2)0.055 (2)0.0165 (17)0.0026 (18)0.0152 (19)
C50.042 (2)0.063 (2)0.045 (2)0.0168 (18)0.0016 (17)0.015 (2)
C60.045 (2)0.056 (2)0.040 (2)0.0031 (17)0.0061 (16)0.0220 (18)
C70.0342 (17)0.0421 (18)0.0356 (18)0.0022 (14)0.0110 (14)0.0143 (15)
C80.047 (2)0.048 (2)0.050 (2)0.0026 (17)0.0127 (18)0.0247 (18)
C90.0250 (14)0.0271 (14)0.0404 (18)0.0017 (11)0.0066 (13)0.0118 (13)
C100.0305 (17)0.061 (2)0.055 (2)0.0147 (16)0.0066 (16)0.008 (2)
C110.0368 (19)0.054 (2)0.045 (2)0.0106 (16)0.0113 (16)0.0013 (18)
C120.0251 (15)0.0356 (17)0.052 (2)0.0005 (12)0.0098 (14)0.0234 (16)
C130.0267 (14)0.0286 (15)0.0361 (17)0.0015 (12)0.0129 (13)0.0131 (13)
C140.0278 (15)0.0263 (14)0.0412 (18)0.0008 (12)0.0115 (13)0.0140 (13)
C150.0377 (18)0.0273 (16)0.060 (2)0.0044 (13)0.0153 (16)0.0172 (16)
C160.045 (2)0.0293 (16)0.064 (2)0.0041 (14)0.0206 (18)0.0236 (17)
C170.0334 (17)0.0384 (18)0.060 (2)0.0063 (14)0.0105 (16)0.0251 (17)
C180.0278 (16)0.0349 (17)0.053 (2)0.0021 (13)0.0063 (15)0.0185 (16)
C190.0290 (15)0.0249 (14)0.0373 (17)0.0006 (11)0.0110 (13)0.0133 (13)
Geometric parameters (Å, º) top
Cd1—N32.266 (2)C3—H30.9300
Cd1—N12.306 (3)C4—C51.374 (5)
Cd1—O12.350 (3)C4—H40.9300
Cd1—O22.506 (3)C5—C61.370 (5)
Cd1—Cl1i2.5551 (10)C5—H50.9300
Cd1—Cl12.6605 (13)C6—C71.404 (5)
Cd1—C12.756 (3)C6—H60.9300
Cl1—Cd1i2.5550 (10)C7—C81.533 (5)
O1—C11.197 (4)C9—H90.9300
O2—C11.242 (4)C10—C111.343 (5)
O3—C81.294 (4)C10—H100.9300
O3—H3A0.8200C11—H110.9300
O4—C81.211 (4)C12—C13ii1.492 (4)
N1—C91.315 (4)C12—H12A0.9700
N1—C101.359 (5)C12—H12B0.9700
N2—C91.332 (4)C13—C12iii1.492 (4)
N2—C111.366 (4)C14—C191.385 (4)
N2—C121.459 (4)C14—C151.389 (4)
N3—C131.316 (4)C15—C161.372 (5)
N3—C191.400 (3)C15—H150.9300
N4—C131.349 (4)C16—C171.394 (5)
N4—C141.383 (4)C16—H160.9300
N4—H4A0.8600C17—C181.377 (4)
C1—C21.553 (4)C17—H170.9300
C2—C31.404 (4)C18—C191.392 (4)
C2—C71.412 (4)C18—H180.9300
C3—C41.364 (5)
N3—Cd1—N193.26 (9)C3—C4—H4120.2
N3—Cd1—O1145.11 (9)C5—C4—H4120.2
N1—Cd1—O183.65 (9)C6—C5—C4120.0 (4)
N3—Cd1—O293.14 (9)C6—C5—H5120.0
N1—Cd1—O290.98 (9)C4—C5—H5120.0
O1—Cd1—O252.34 (8)C5—C6—C7121.8 (4)
N3—Cd1—Cl1i110.50 (7)C5—C6—H6119.1
N1—Cd1—Cl1i92.18 (7)C7—C6—H6119.1
O1—Cd1—Cl1i104.36 (7)C6—C7—C2118.1 (3)
O2—Cd1—Cl1i155.92 (6)C6—C7—C8112.8 (3)
N3—Cd1—Cl196.35 (7)C2—C7—C8129.0 (3)
N1—Cd1—Cl1170.33 (7)O4—C8—O3119.6 (3)
O1—Cd1—Cl189.04 (7)O4—C8—C7119.5 (4)
O2—Cd1—Cl189.54 (6)O3—C8—C7120.9 (3)
Cl1i—Cd1—Cl183.49 (3)N1—C9—N2111.6 (3)
N3—Cd1—C1119.75 (9)N1—C9—H9124.2
N1—Cd1—C186.69 (9)N2—C9—H9124.2
O1—Cd1—C125.56 (8)C11—C10—N1110.2 (3)
O2—Cd1—C126.78 (8)C11—C10—H10124.9
Cl1i—Cd1—C1129.73 (7)N1—C10—H10124.9
Cl1—Cd1—C189.44 (6)C10—C11—N2106.0 (3)
Cd1i—Cl1—Cd196.51 (3)C10—C11—H11127.0
C1—O1—Cd196.5 (2)N2—C11—H11127.0
C1—O2—Cd187.9 (2)N2—C12—C13ii113.8 (2)
C8—O3—H3A109.5N2—C12—H12A108.8
C9—N1—C10105.2 (3)C13ii—C12—H12A108.8
C9—N1—Cd1129.7 (2)N2—C12—H12B108.8
C10—N1—Cd1124.7 (2)C13ii—C12—H12B108.8
C9—N2—C11106.9 (3)H12A—C12—H12B107.7
C9—N2—C12126.7 (3)N3—C13—N4112.2 (3)
C11—N2—C12126.3 (3)N3—C13—C12iii123.6 (3)
C13—N3—C19105.4 (2)N4—C13—C12iii124.1 (3)
C13—N3—Cd1130.38 (19)N4—C14—C19105.4 (2)
C19—N3—Cd1123.57 (18)N4—C14—C15132.0 (3)
C13—N4—C14107.7 (2)C19—C14—C15122.6 (3)
C13—N4—H4A126.1C16—C15—C14116.6 (3)
C14—N4—H4A126.1C16—C15—H15121.7
O1—C1—O2123.2 (3)C14—C15—H15121.7
O1—C1—C2117.6 (3)C15—C16—C17121.6 (3)
O2—C1—C2119.1 (3)C15—C16—H16119.2
O1—C1—Cd157.90 (17)C17—C16—H16119.2
O2—C1—Cd165.35 (18)C18—C17—C16121.5 (3)
C2—C1—Cd1175.0 (2)C18—C17—H17119.3
C3—C2—C7118.0 (3)C16—C17—H17119.3
C3—C2—C1113.3 (3)C17—C18—C19117.6 (3)
C7—C2—C1128.7 (3)C17—C18—H18121.2
C4—C3—C2122.4 (3)C19—C18—H18121.2
C4—C3—H3118.8C14—C19—C18120.1 (3)
C2—C3—H3118.8C14—C19—N3109.2 (2)
C3—C4—C5119.6 (4)C18—C19—N3130.7 (3)
Cd1—O1—C1—O21.1 (3)N1—C10—C11—N20.1 (5)
Cd1—O1—C1—C2177.5 (2)C9—N2—C11—C100.0 (4)
Cd1—O2—C1—O11.0 (3)C12—N2—C11—C10179.2 (3)
Cd1—O2—C1—C2177.5 (2)C9—N2—C12—C13ii98.3 (4)
O1—C1—C2—C30.6 (4)C11—N2—C12—C13ii82.7 (4)
O2—C1—C2—C3178.0 (3)C19—N3—C13—N40.9 (3)
O1—C1—C2—C7179.4 (3)Cd1—N3—C13—N4170.2 (2)
O2—C1—C2—C72.0 (5)C19—N3—C13—C12iii175.0 (3)
C7—C2—C3—C40.2 (5)Cd1—N3—C13—C12iii13.9 (5)
C1—C2—C3—C4179.8 (3)C14—N4—C13—N30.5 (4)
C2—C3—C4—C50.7 (6)C14—N4—C13—C12iii175.4 (3)
C3—C4—C5—C61.2 (6)C13—N4—C14—C190.2 (3)
C4—C5—C6—C70.8 (6)C13—N4—C14—C15179.9 (3)
C5—C6—C7—C20.1 (5)N4—C14—C15—C16179.3 (3)
C5—C6—C7—C8179.6 (3)C19—C14—C15—C160.4 (5)
C3—C2—C7—C60.6 (5)C14—C15—C16—C170.4 (5)
C1—C2—C7—C6179.5 (3)C15—C16—C17—C181.2 (6)
C3—C2—C7—C8179.9 (3)C16—C17—C18—C191.0 (5)
C1—C2—C7—C80.0 (5)N4—C14—C19—C18179.2 (3)
C6—C7—C8—O41.4 (5)C15—C14—C19—C180.6 (5)
C2—C7—C8—O4178.1 (4)N4—C14—C19—N30.7 (3)
C6—C7—C8—O3178.6 (3)C15—C14—C19—N3179.5 (3)
C2—C7—C8—O31.9 (6)C17—C18—C19—C140.1 (5)
C10—N1—C9—N20.2 (4)C17—C18—C19—N3179.8 (3)
Cd1—N1—C9—N2172.92 (19)C13—N3—C19—C141.0 (3)
C11—N2—C9—N10.2 (4)Cd1—N3—C19—C14170.8 (2)
C12—N2—C9—N1179.3 (3)C13—N3—C19—C18178.9 (3)
C9—N1—C10—C110.2 (4)Cd1—N3—C19—C189.3 (5)
Cd1—N1—C10—C11173.4 (3)
Symmetry codes: (i) x+1, y, z+1; (ii) x1, y, z; (iii) x+1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3A···O20.821.622.436 (3)179
N4—H4A···O3iv0.862.172.931 (4)147
Symmetry code: (iv) x+1, y+1, z+1.
Poly[[aqua(µ2-benzene-1,3-dicarboxylato-κ3O1,O1':O3){µ2-2-[(1H-imidazol-1-yl)methyl]-1H-benzimidazole-κ2N:N'}cadmium(II)] dihydrate] (II) top
Crystal data top
[Cd(C8H4O4)(C11H10N4)(H2O)]·2H2OZ = 2
Mr = 528.79F(000) = 532
Triclinic, P1Dx = 1.723 Mg m3
a = 8.9624 (18) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.256 (2) ÅCell parameters from 3521 reflections
c = 13.070 (3) Åθ = 1.7–27.8°
α = 96.13 (3)°µ = 1.12 mm1
β = 106.88 (3)°T = 293 K
γ = 113.57 (3)°Prism, colourless
V = 1019.1 (5) Å30.19 × 0.18 × 0.14 mm
Data collection top
Rigaku Saturn
diffractometer
4811 independent reflections
Radiation source: fine-focus sealed tube4470 reflections with I > 2σ(I)
Detector resolution: 28.5714 pixels mm-1Rint = 0.028
ω scansθmax = 27.9°, θmin = 2.2°
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2004)
h = 1111
Tmin = 0.888, Tmax = 1.000k = 1313
12704 measured reflectionsl = 1717
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.032Hydrogen site location: mixed
wR(F2) = 0.066H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.0227P)2 + 0.8447P]
where P = (Fo2 + 2Fc2)/3
4811 reflections(Δ/σ)max = 0.001
280 parametersΔρmax = 0.37 e Å3
0 restraintsΔρmin = 0.41 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
Cd10.68944 (2)0.12523 (2)0.21128 (2)0.02528 (6)
O10.6919 (3)0.3532 (2)0.20252 (17)0.0380 (4)
O20.7223 (3)0.2578 (2)0.05649 (18)0.0470 (5)
O30.6629 (3)0.8389 (3)0.23059 (18)0.0516 (6)
O40.7067 (3)0.9521 (2)0.10100 (16)0.0372 (4)
O50.3880 (2)0.0067 (2)0.10119 (15)0.0360 (4)
H5A0.36190.09520.07320.054*
H5B0.35630.02380.04470.054*
N10.9928 (3)0.2305 (2)0.28645 (19)0.0318 (5)
N21.2513 (3)0.2510 (2)0.29902 (17)0.0291 (5)
N30.6203 (3)0.1540 (2)0.36356 (16)0.0259 (4)
N40.5000 (3)0.2142 (3)0.47502 (17)0.0311 (5)
H4C0.43050.23880.49620.037*
C11.0802 (3)0.1616 (3)0.2643 (2)0.0326 (6)
H11.02900.06230.22880.039*
C21.1158 (4)0.3728 (4)0.3365 (3)0.0444 (7)
H21.09280.44850.36150.053*
C31.2755 (4)0.3875 (3)0.3445 (3)0.0443 (7)
H31.38070.47320.37480.053*
C41.3791 (4)0.2113 (4)0.2755 (2)0.0372 (7)
H4A1.44880.28700.24700.045*
H4B1.31690.12030.21770.045*
C50.4994 (3)0.1919 (3)0.3718 (2)0.0274 (5)
C60.6330 (3)0.1902 (3)0.5405 (2)0.0294 (5)
C70.6936 (4)0.2002 (3)0.6534 (2)0.0409 (7)
H70.64170.22420.69970.049*
C80.8353 (4)0.1724 (4)0.6923 (2)0.0489 (8)
H80.88180.17960.76740.059*
C90.9112 (4)0.1341 (4)0.6230 (3)0.0471 (8)
H91.00650.11610.65300.057*
C100.8489 (4)0.1220 (3)0.5109 (2)0.0370 (6)
H100.89870.09450.46460.044*
C110.7082 (3)0.1527 (3)0.4703 (2)0.0277 (5)
C120.7150 (3)0.3602 (3)0.1122 (2)0.0294 (5)
C130.7389 (3)0.4968 (3)0.0734 (2)0.0276 (5)
C140.8044 (4)0.5227 (3)0.0100 (2)0.0403 (7)
H140.82620.45220.04500.048*
C150.8375 (5)0.6523 (4)0.0414 (3)0.0517 (9)
H150.88530.67060.09580.062*
C160.7996 (4)0.7556 (3)0.0080 (2)0.0407 (7)
H160.82100.84260.01400.049*
C170.7299 (3)0.7302 (3)0.0900 (2)0.0280 (5)
C180.7018 (3)0.6010 (3)0.1230 (2)0.0269 (5)
H180.65760.58380.17900.032*
C190.6940 (3)0.8451 (3)0.1449 (2)0.0312 (6)
O60.6667 (3)0.7024 (3)0.4051 (2)0.0616 (7)
H6A0.66910.74300.35180.092*
H6B0.73570.67060.43960.092*
O70.8453 (5)0.5288 (3)0.4128 (2)0.0909 (10)
H7A0.80670.46040.35510.136*
H7B0.90440.59820.38920.136*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cd10.02621 (10)0.02688 (10)0.02839 (10)0.01539 (8)0.01257 (7)0.00763 (7)
O10.0502 (12)0.0338 (10)0.0451 (11)0.0250 (9)0.0259 (10)0.0200 (9)
O20.0682 (15)0.0280 (10)0.0486 (13)0.0293 (11)0.0174 (11)0.0047 (9)
O30.0832 (17)0.0559 (14)0.0469 (13)0.0510 (13)0.0365 (12)0.0184 (11)
O40.0485 (12)0.0273 (10)0.0414 (11)0.0252 (9)0.0130 (9)0.0078 (8)
O50.0382 (11)0.0339 (10)0.0323 (10)0.0184 (9)0.0079 (8)0.0002 (8)
N10.0242 (11)0.0362 (12)0.0399 (12)0.0169 (10)0.0134 (10)0.0105 (10)
N20.0237 (11)0.0392 (13)0.0297 (11)0.0184 (10)0.0112 (9)0.0085 (10)
N30.0244 (10)0.0326 (11)0.0269 (10)0.0165 (9)0.0119 (9)0.0094 (9)
N40.0281 (11)0.0443 (13)0.0283 (11)0.0210 (10)0.0139 (9)0.0084 (10)
C10.0280 (13)0.0332 (14)0.0402 (15)0.0174 (11)0.0120 (11)0.0104 (12)
C20.0387 (17)0.0456 (18)0.0492 (18)0.0254 (14)0.0125 (14)0.0031 (14)
C30.0286 (15)0.0368 (16)0.0544 (19)0.0110 (12)0.0078 (13)0.0029 (14)
C40.0300 (14)0.064 (2)0.0299 (13)0.0314 (14)0.0136 (11)0.0125 (13)
C50.0220 (12)0.0344 (14)0.0282 (12)0.0139 (10)0.0110 (10)0.0073 (11)
C60.0264 (13)0.0318 (14)0.0283 (13)0.0118 (11)0.0096 (10)0.0072 (11)
C70.0423 (17)0.0493 (18)0.0304 (14)0.0193 (14)0.0138 (13)0.0123 (13)
C80.0442 (18)0.066 (2)0.0324 (15)0.0225 (16)0.0080 (13)0.0244 (15)
C90.0316 (16)0.066 (2)0.0485 (18)0.0263 (15)0.0099 (13)0.0308 (16)
C100.0313 (14)0.0462 (17)0.0438 (16)0.0227 (13)0.0166 (12)0.0210 (14)
C110.0215 (12)0.0301 (13)0.0305 (13)0.0103 (10)0.0091 (10)0.0108 (11)
C120.0241 (12)0.0224 (12)0.0393 (14)0.0122 (10)0.0063 (11)0.0066 (11)
C130.0310 (13)0.0240 (12)0.0295 (13)0.0161 (11)0.0081 (10)0.0067 (10)
C140.064 (2)0.0416 (16)0.0393 (15)0.0390 (15)0.0277 (15)0.0156 (13)
C150.088 (3)0.059 (2)0.0500 (18)0.053 (2)0.0483 (19)0.0333 (17)
C160.060 (2)0.0386 (16)0.0439 (16)0.0333 (15)0.0263 (15)0.0229 (13)
C170.0298 (13)0.0260 (13)0.0313 (13)0.0174 (11)0.0088 (11)0.0068 (10)
C180.0292 (13)0.0264 (13)0.0296 (13)0.0160 (11)0.0120 (10)0.0074 (10)
C190.0305 (14)0.0278 (13)0.0341 (14)0.0185 (11)0.0046 (11)0.0031 (11)
O60.0771 (17)0.0895 (19)0.0635 (15)0.0585 (16)0.0505 (14)0.0381 (14)
O70.139 (3)0.0602 (18)0.0689 (19)0.0509 (19)0.0290 (19)0.0007 (15)
Geometric parameters (Å, º) top
Cd1—O4i2.2487 (19)C4—H4B0.9700
Cd1—N32.274 (2)C5—C4iv1.491 (3)
Cd1—N12.323 (2)C6—C111.392 (3)
Cd1—O12.3450 (19)C6—C71.393 (4)
Cd1—O52.367 (2)C7—C81.378 (4)
Cd1—O22.577 (2)C7—H70.9300
O1—C121.261 (3)C8—C91.390 (5)
O2—C121.248 (3)C8—H80.9300
O3—C191.232 (3)C9—C101.380 (4)
O4—C191.273 (3)C9—H90.9300
O4—Cd1ii2.2487 (19)C10—C111.391 (3)
O5—H5A0.8500C10—H100.9300
O5—H5B0.8501C12—C131.497 (4)
N1—C11.314 (3)C13—C141.384 (4)
N1—C21.366 (4)C13—C181.390 (3)
N2—C11.334 (3)C14—C151.377 (4)
N2—C31.365 (4)C14—H140.9300
N2—C41.457 (3)C15—C161.387 (4)
N3—C51.316 (3)C15—H150.9300
N3—C111.394 (3)C16—C171.388 (4)
N4—C51.342 (3)C16—H160.9300
N4—C61.379 (3)C17—C181.387 (3)
N4—H4C0.8599C17—C191.505 (3)
C1—H10.9300C18—H180.9300
C2—C31.349 (4)O6—H6A0.8501
C2—H20.9300O6—H6B0.8500
C3—H30.9300O7—H7A0.8500
C4—C5iii1.491 (3)O7—H7B0.8500
C4—H4A0.9700
O4i—Cd1—N3139.23 (8)N3—C5—N4113.1 (2)
O4i—Cd1—N185.63 (8)N3—C5—C4iv122.4 (2)
N3—Cd1—N1102.23 (8)N4—C5—C4iv124.5 (2)
O4i—Cd1—O1135.48 (7)N4—C6—C11105.8 (2)
N3—Cd1—O184.65 (8)N4—C6—C7131.5 (3)
N1—Cd1—O192.40 (8)C11—C6—C7122.6 (3)
O4i—Cd1—O582.68 (8)C8—C7—C6115.8 (3)
N3—Cd1—O589.69 (8)C8—C7—H7122.1
N1—Cd1—O5167.43 (7)C6—C7—H7122.1
O1—Cd1—O592.68 (8)C7—C8—C9122.2 (3)
O4i—Cd1—O282.93 (7)C7—C8—H8118.9
N3—Cd1—O2136.73 (7)C9—C8—H8118.9
N1—Cd1—O287.33 (8)C10—C9—C8121.8 (3)
O1—Cd1—O252.56 (7)C10—C9—H9119.1
O5—Cd1—O286.65 (8)C8—C9—H9119.1
C12—O1—Cd198.23 (16)C9—C10—C11116.9 (3)
C12—O2—Cd187.68 (17)C9—C10—H10121.5
C19—O4—Cd1ii109.56 (17)C11—C10—H10121.5
Cd1—O5—H5A110.5C6—C11—C10120.6 (2)
Cd1—O5—H5B114.5C6—C11—N3108.8 (2)
H5A—O5—H5B102.9C10—C11—N3130.5 (2)
C1—N1—C2105.0 (2)O2—C12—O1121.5 (2)
C1—N1—Cd1122.19 (19)O2—C12—C13119.9 (3)
C2—N1—Cd1131.29 (18)O1—C12—C13118.6 (2)
C1—N2—C3106.9 (2)C14—C13—C18119.4 (2)
C1—N2—C4124.8 (2)C14—C13—C12119.8 (2)
C3—N2—C4127.7 (2)C18—C13—C12120.8 (2)
C5—N3—C11105.2 (2)C15—C14—C13120.3 (3)
C5—N3—Cd1126.60 (17)C15—C14—H14119.9
C11—N3—Cd1127.82 (16)C13—C14—H14119.9
C5—N4—C6107.1 (2)C14—C15—C16120.0 (3)
C5—N4—H4C126.4C14—C15—H15120.0
C6—N4—H4C126.5C16—C15—H15120.0
N1—C1—N2112.0 (2)C15—C16—C17120.5 (3)
N1—C1—H1124.0C15—C16—H16119.8
N2—C1—H1124.0C17—C16—H16119.8
C3—C2—N1110.1 (3)C18—C17—C16118.8 (2)
C3—C2—H2125.0C18—C17—C19121.3 (2)
N1—C2—H2125.0C16—C17—C19119.8 (2)
C2—C3—N2106.1 (3)C17—C18—C13120.9 (2)
C2—C3—H3127.0C17—C18—H18119.6
N2—C3—H3127.0C13—C18—H18119.6
N2—C4—C5iii115.1 (2)O3—C19—O4122.3 (2)
N2—C4—H4A108.5O3—C19—C17121.5 (2)
C5iii—C4—H4A108.5O4—C19—C17116.2 (2)
N2—C4—H4B108.5H6A—O6—H6B129.3
C5iii—C4—H4B108.5H7A—O7—H7B96.6
H4A—C4—H4B107.5
C2—N1—C1—N21.1 (3)C9—C10—C11—N3178.2 (3)
Cd1—N1—C1—N2168.39 (17)C5—N3—C11—C60.5 (3)
C3—N2—C1—N11.3 (3)Cd1—N3—C11—C6173.58 (17)
C4—N2—C1—N1172.7 (2)C5—N3—C11—C10179.2 (3)
C1—N1—C2—C30.4 (4)Cd1—N3—C11—C106.1 (4)
Cd1—N1—C2—C3166.1 (2)Cd1—O2—C12—O12.4 (3)
N1—C2—C3—N20.4 (4)Cd1—O2—C12—C13175.9 (2)
C1—N2—C3—C21.0 (3)Cd1—O1—C12—O22.6 (3)
C4—N2—C3—C2172.1 (3)Cd1—O1—C12—C13175.69 (19)
C1—N2—C4—C5iii108.5 (3)O2—C12—C13—C1413.5 (4)
C3—N2—C4—C5iii81.9 (4)O1—C12—C13—C14164.9 (3)
C11—N3—C5—N40.6 (3)O2—C12—C13—C18168.8 (2)
Cd1—N3—C5—N4173.83 (16)O1—C12—C13—C1812.8 (4)
C11—N3—C5—C4iv177.9 (2)C18—C13—C14—C151.9 (4)
Cd1—N3—C5—C4iv4.6 (4)C12—C13—C14—C15175.8 (3)
C6—N4—C5—N30.5 (3)C13—C14—C15—C162.2 (5)
C6—N4—C5—C4iv177.9 (3)C14—C15—C16—C170.7 (5)
C5—N4—C6—C110.2 (3)C15—C16—C17—C181.1 (4)
C5—N4—C6—C7178.7 (3)C15—C16—C17—C19178.4 (3)
N4—C6—C7—C8177.9 (3)C16—C17—C18—C131.4 (4)
C11—C6—C7—C80.8 (4)C19—C17—C18—C13178.6 (2)
C6—C7—C8—C91.1 (5)C14—C13—C18—C170.1 (4)
C7—C8—C9—C100.2 (5)C12—C13—C18—C17177.6 (2)
C8—C9—C10—C111.2 (5)Cd1ii—O4—C19—O35.2 (3)
N4—C6—C11—C10179.6 (2)Cd1ii—O4—C19—C17171.14 (17)
C7—C6—C11—C100.6 (4)C18—C17—C19—O310.7 (4)
N4—C6—C11—N30.2 (3)C16—C17—C19—O3166.6 (3)
C7—C6—C11—N3179.2 (2)C18—C17—C19—O4172.9 (2)
C9—C10—C11—C61.5 (4)C16—C17—C19—O49.8 (4)
Symmetry codes: (i) x, y1, z; (ii) x, y+1, z; (iii) x+1, y, z; (iv) x1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4C···O6v0.861.922.741 (3)159
O5—H5A···O2vi0.851.972.739 (3)151
O5—H5B···O4vii0.851.902.722 (3)164
O6—H6A···O30.851.952.800 (3)176
O6—H6B···O70.852.112.823 (4)142
O7—H7A···O10.851.922.730 (4)160
Symmetry codes: (v) x+1, y+1, z+1; (vi) x+1, y, z; (vii) x+1, y+1, z.
 

Follow Acta Cryst. C
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds