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metal-organic compounds
Poly[[(μ2-benzene-1,3-dicarboxylato){μ2-1,4-bis[(1H-imidazol-1-yl)methyl]benzene}cadmium] dimethylformamide monosolvate]
aDepartment of General Surgery, The First Hospital, Jilin University, Changchun, 130021 Jilin Province, People's Republic of China
*Correspondence e-mail: suojian0007@163.com
The title coordination polymer, {[Cd(C8H4O4)(C14H14N4)]·C3H7NO}n, was synthesized by solvothermal reaction of metallic cadmium with the semi-rigid neutral ligand 1,4-bis[(1H-imidazol-1-yl)methyl]benzene (bix) and the V-shaped benzene-1,3-dicarboxylic acid (m-H2bdc). The structure exhibits a pseudo-C-centring which is almost fulfilled by the polymeric metal complex but not by the solvent dimethylformamide (DMF) molecules. The contains two independent CdII ions, two m-bdc2− ligands, one and two half bix ligands, and two solvent DMF molecules. The CdII ions are both five-coordinated by three O atoms from two different m-bdc2− ligands and two N atoms from two different bix ligands in a distorted square-pyramidal geometry. The m-bdc2− ligands adopt a chelate-monodentate coordination mode, connecting neighboring CdII ions into a zigzag chain parallel to [110]. Adjacent chains are further cross-linked by bix ligands, giving rise to a puckered sheet nearly perpendicular to the chain direction. Thus, each CdII ion is connected to four neighboring CdII ions through two m-bdc2− anions and two bix ligands, giving rise to the final non-interpenetrating uninodal layer with sql (4,4) topology.
CCDC reference: 966467
Related literature
For background compounds with metal-organic framework structurs, see: Batten & Robson (1998); Chen et al. (2011
); Farrusseng et al. (2009
); Kurmoo (2009
); Pramanik et al. (2011
); Wong et al. (2006
). For topologies, see: Blatov et al. (2010
). For a description of the geometry of complexes with five-coordinate metal atoms, see: Addison et al. (1984
).
Experimental
Crystal data
|
Data collection: APEX2 (Bruker, 2007); cell SAINT (Bruker, 2007
); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008
); program(s) used to refine structure: SHELXTL; molecular graphics: XP in SHELXTL and DIAMOND (Brandenburg, 1999
); software used to prepare material for publication: SHELXTL.
Supporting information
CCDC reference: 966467
10.1107/S1600536813028298/bt6934sup1.cif
contains datablocks Suo1, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536813028298/bt6934Isup2.hkl
A mixture of Cd(NO3)2·4H2O (0.0304 g, 0.1 mmol), m-H2bdc (0.0164 g, 0.1 mmol), bix (0.0238 g, 0.1 mmol), and DMF (6 ml) was placed in a 15 ml PTFE-lined stainless steel vessel under autogenous pressure, heated at a constant 95 °C for 72 h, and allowed to cool down to room temperature in 12 h. The title crystals were collected, washed with DMF and EtOH, and dried under ambient conditions with a yield of 13% based on Cd).
All the hydrogen atoms attached to carbon atoms were placed in calculated positions and refined as the riding model.
Data collection: APEX2 (Bruker, 2007); cell
SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).[Cd(C8H4O4)(C14H14N4)]·C3H7NO | V = 2488.37 (16) Å3 |
Mr = 587.90 | Z = 4 |
Triclinic, P1 | F(000) = 1192 |
Hall symbol: -P 1 | Dx = 1.569 Mg m−3 |
a = 11.2088 (4) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 13.4710 (5) Å | µ = 0.92 mm−1 |
c = 18.9133 (7) Å | T = 185 K |
α = 69.648 (1)° | Needle, colorless |
β = 80.124 (1)° | 0.26 × 0.23 × 0.13 mm |
γ = 68.521 (1)° |
Bruker APEXII CCD diffractometer | 9746 independent reflections |
Radiation source: fine-focus sealed tube | 6383 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.017 |
ϕ and ω scans | θmax = 26.1°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Bruker, 2007) | h = −13→13 |
Tmin = 0.795, Tmax = 0.889 | k = −10→16 |
13952 measured reflections | l = −21→23 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.034 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.095 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0431P)2 + 0.3924P] where P = (Fo2 + 2Fc2)/3 |
9746 reflections | (Δ/σ)max = 0.010 |
649 parameters | Δρmax = 0.61 e Å−3 |
0 restraints | Δρmin = −0.51 e Å−3 |
[Cd(C8H4O4)(C14H14N4)]·C3H7NO | γ = 68.521 (1)° |
Mr = 587.90 | V = 2488.37 (16) Å3 |
Triclinic, P1 | Z = 4 |
a = 11.2088 (4) Å | Mo Kα radiation |
b = 13.4710 (5) Å | µ = 0.92 mm−1 |
c = 18.9133 (7) Å | T = 185 K |
α = 69.648 (1)° | 0.26 × 0.23 × 0.13 mm |
β = 80.124 (1)° |
Bruker APEXII CCD diffractometer | 9746 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2007) | 6383 reflections with I > 2σ(I) |
Tmin = 0.795, Tmax = 0.889 | Rint = 0.017 |
13952 measured reflections |
R[F2 > 2σ(F2)] = 0.034 | 0 restraints |
wR(F2) = 0.095 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.61 e Å−3 |
9746 reflections | Δρmin = −0.51 e Å−3 |
649 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
C1 | 1.1683 (3) | 0.2415 (3) | 0.29177 (18) | 0.0219 (7) | |
C2 | 1.1610 (3) | 0.1318 (3) | 0.29320 (18) | 0.0214 (7) | |
C3 | 1.0430 (3) | 0.1167 (3) | 0.29977 (18) | 0.0212 (7) | |
H3 | 0.9666 | 0.1749 | 0.3063 | 0.025* | |
C4 | 1.0352 (3) | 0.0174 (3) | 0.29695 (18) | 0.0215 (7) | |
C5 | 1.1478 (3) | −0.0674 (3) | 0.28762 (19) | 0.0268 (8) | |
H5 | 1.1435 | −0.1350 | 0.2846 | 0.032* | |
C6 | 1.2658 (3) | −0.0539 (3) | 0.2827 (2) | 0.0285 (8) | |
H6 | 1.3423 | −0.1126 | 0.2771 | 0.034* | |
C7 | 1.2727 (3) | 0.0442 (3) | 0.28584 (19) | 0.0258 (8) | |
H7 | 1.3541 | 0.0526 | 0.2830 | 0.031* | |
C8 | 0.9071 (3) | 0.0023 (3) | 0.30248 (18) | 0.0236 (8) | |
C9 | 0.3346 (3) | 0.2555 (3) | 0.71091 (17) | 0.0207 (7) | |
C10 | 0.3391 (3) | 0.3651 (3) | 0.71219 (18) | 0.0216 (7) | |
C11 | 0.4556 (3) | 0.3833 (3) | 0.70514 (17) | 0.0212 (7) | |
H11 | 0.5331 | 0.3271 | 0.6972 | 0.025* | |
C12 | 0.4597 (3) | 0.4824 (3) | 0.70960 (18) | 0.0227 (7) | |
C13 | 0.3459 (3) | 0.5646 (3) | 0.7210 (2) | 0.0297 (8) | |
H13 | 0.3482 | 0.6322 | 0.7251 | 0.036* | |
C14 | 0.2295 (3) | 0.5482 (3) | 0.7265 (2) | 0.0349 (9) | |
H14 | 0.1518 | 0.6051 | 0.7333 | 0.042* | |
C15 | 0.2262 (3) | 0.4491 (3) | 0.7220 (2) | 0.0281 (8) | |
H15 | 0.1460 | 0.4382 | 0.7257 | 0.034* | |
C16 | 0.5861 (3) | 0.5015 (3) | 0.70207 (19) | 0.0254 (8) | |
C17 | 1.0306 (3) | 0.3691 (3) | 0.44554 (18) | 0.0245 (8) | |
H17 | 0.9744 | 0.3644 | 0.4154 | 0.029* | |
C18 | 1.1861 (3) | 0.3961 (3) | 0.4807 (2) | 0.0288 (8) | |
H18 | 1.2608 | 0.4145 | 0.4792 | 0.035* | |
C19 | 1.1161 (3) | 0.3602 (3) | 0.5442 (2) | 0.0290 (8) | |
H19 | 1.1322 | 0.3489 | 0.5946 | 0.035* | |
C20 | 0.9167 (3) | 0.3069 (3) | 0.57294 (19) | 0.0301 (8) | |
H20A | 0.8631 | 0.3673 | 0.5946 | 0.036* | |
H20B | 0.9574 | 0.2399 | 0.6151 | 0.036* | |
C21 | 0.8322 (3) | 0.2789 (3) | 0.53413 (19) | 0.0272 (8) | |
C22 | 0.8780 (3) | 0.1888 (3) | 0.5069 (2) | 0.0352 (9) | |
H22 | 0.9659 | 0.1436 | 0.5116 | 0.042* | |
C23 | 0.7991 (3) | 0.1625 (3) | 0.4728 (2) | 0.0333 (9) | |
H23 | 0.8334 | 0.1003 | 0.4539 | 0.040* | |
C24 | 0.6703 (3) | 0.2262 (3) | 0.46594 (19) | 0.0285 (8) | |
C25 | 0.6239 (3) | 0.3168 (3) | 0.4934 (2) | 0.0366 (9) | |
H25 | 0.5359 | 0.3618 | 0.4891 | 0.044* | |
C26 | 0.7035 (3) | 0.3430 (3) | 0.5270 (2) | 0.0342 (9) | |
H26 | 0.6697 | 0.4056 | 0.5454 | 0.041* | |
C27 | 0.5851 (3) | 0.1979 (3) | 0.42727 (19) | 0.0317 (9) | |
H27A | 0.5425 | 0.2654 | 0.3860 | 0.038* | |
H27B | 0.6390 | 0.1390 | 0.4044 | 0.038* | |
C28 | 0.4746 (3) | 0.1321 (3) | 0.55469 (19) | 0.0246 (8) | |
H28 | 0.5299 | 0.1384 | 0.5846 | 0.030* | |
C29 | 0.3222 (3) | 0.0997 (3) | 0.52056 (19) | 0.0268 (8) | |
H29 | 0.2493 | 0.0787 | 0.5224 | 0.032* | |
C30 | 0.3898 (3) | 0.1378 (3) | 0.4571 (2) | 0.0271 (8) | |
H30 | 0.3737 | 0.1482 | 0.4068 | 0.032* | |
C31 | 1.0636 (3) | 0.6731 (3) | 0.20771 (18) | 0.0257 (8) | |
H31 | 1.0874 | 0.6998 | 0.2417 | 0.031* | |
C32 | 1.0492 (3) | 0.5644 (3) | 0.1510 (2) | 0.0318 (9) | |
H32 | 1.0618 | 0.4994 | 0.1377 | 0.038* | |
C33 | 0.9706 (3) | 0.6695 (3) | 0.1168 (2) | 0.0315 (9) | |
H33 | 0.9187 | 0.6914 | 0.0756 | 0.038* | |
C34 | 0.9112 (3) | 0.8574 (3) | 0.13767 (19) | 0.0286 (8) | |
H34A | 0.9193 | 0.8803 | 0.1805 | 0.034* | |
H34B | 0.8190 | 0.8714 | 0.1341 | 0.034* | |
C35 | 0.9595 (3) | 0.9290 (3) | 0.06538 (19) | 0.0248 (8) | |
C36 | 0.8811 (3) | 1.0373 (3) | 0.0336 (2) | 0.0331 (9) | |
H36 | 0.7984 | 1.0642 | 0.0564 | 0.040* | |
C44 | 0.4296 (4) | −0.4321 (4) | 0.9400 (2) | 0.0576 (14) | |
H44 | 0.3780 | −0.3844 | 0.8982 | 0.069* | |
C42 | 0.5491 (3) | −0.4309 (3) | 0.93834 (19) | 0.0279 (8) | |
C43 | 0.6209 (4) | −0.4991 (4) | 0.9993 (2) | 0.0574 (14) | |
H43 | 0.7055 | −0.4995 | 1.0001 | 0.069* | |
C37 | 1.0787 (3) | 0.8924 (3) | 0.0312 (2) | 0.0343 (9) | |
H37 | 1.1342 | 0.8180 | 0.0522 | 0.041* | |
C41 | 0.6045 (3) | −0.3580 (3) | 0.8699 (2) | 0.0335 (9) | |
H41A | 0.6931 | −0.3683 | 0.8795 | 0.040* | |
H41B | 0.6089 | −0.3825 | 0.8257 | 0.040* | |
C38 | 0.4515 (3) | −0.1767 (3) | 0.79481 (18) | 0.0253 (8) | |
H38 | 0.4364 | −0.2054 | 0.7591 | 0.030* | |
C39 | 0.4469 (3) | −0.0653 (3) | 0.85416 (19) | 0.0290 (8) | |
H39 | 0.4269 | 0.0008 | 0.8679 | 0.035* | |
C40 | 0.5253 (3) | −0.1676 (3) | 0.8912 (2) | 0.0305 (9) | |
H40 | 0.5702 | −0.1870 | 0.9350 | 0.037* | |
C45 | 0.3929 (4) | 0.2343 (4) | 0.9062 (2) | 0.0527 (12) | |
H45 | 0.3385 | 0.3102 | 0.8972 | 0.063* | |
C46 | 0.5744 (5) | 0.2978 (4) | 0.8900 (3) | 0.0687 (15) | |
H46A | 0.6680 | 0.2630 | 0.8904 | 0.103* | |
H46B | 0.5440 | 0.3341 | 0.9295 | 0.103* | |
H46C | 0.5506 | 0.3540 | 0.8407 | 0.103* | |
C47 | 0.6051 (4) | 0.0993 (4) | 0.9156 (3) | 0.0788 (17) | |
H47A | 0.6937 | 0.0985 | 0.9119 | 0.118* | |
H47B | 0.5939 | 0.0702 | 0.8773 | 0.118* | |
H47C | 0.5866 | 0.0521 | 0.9660 | 0.118* | |
C48 | 0.0501 (5) | 0.3563 (4) | 1.0609 (3) | 0.0595 (13) | |
H48 | −0.0195 | 0.4234 | 1.0597 | 0.071* | |
C49 | 0.1270 (4) | 0.1555 (3) | 1.0914 (2) | 0.0478 (11) | |
H49A | 0.0925 | 0.0936 | 1.1143 | 0.072* | |
H49B | 0.1965 | 0.1450 | 1.1212 | 0.072* | |
H49C | 0.1602 | 0.1568 | 1.0398 | 0.072* | |
C50 | −0.1017 (4) | 0.2587 (4) | 1.1177 (3) | 0.0600 (14) | |
H50A | −0.1005 | 0.1808 | 1.1365 | 0.090* | |
H50B | −0.1611 | 0.3016 | 1.0768 | 0.090* | |
H50C | −0.1297 | 0.2919 | 1.1589 | 0.090* | |
N1 | 1.1316 (2) | 0.4017 (2) | 0.41875 (15) | 0.0253 (7) | |
N2 | 1.0180 (3) | 0.3435 (2) | 0.52109 (15) | 0.0235 (6) | |
N3 | 0.3755 (2) | 0.0960 (2) | 0.58225 (15) | 0.0244 (6) | |
N4 | 0.4866 (2) | 0.1584 (2) | 0.47926 (15) | 0.0227 (6) | |
N5 | 1.1076 (3) | 0.5675 (2) | 0.20816 (15) | 0.0261 (7) | |
N6 | 0.9807 (3) | 0.7379 (2) | 0.15290 (15) | 0.0242 (6) | |
N7 | 0.4000 (2) | −0.0710 (2) | 0.79320 (15) | 0.0245 (6) | |
N8 | 0.5273 (3) | −0.2384 (2) | 0.85267 (16) | 0.0260 (7) | |
N9 | 0.5173 (3) | 0.2141 (3) | 0.90346 (19) | 0.0452 (9) | |
N10 | 0.0256 (3) | 0.2612 (3) | 1.08964 (18) | 0.0417 (8) | |
O1 | 1.0681 (2) | 0.32236 (19) | 0.29137 (15) | 0.0343 (6) | |
O2 | 1.2794 (2) | 0.24650 (18) | 0.29156 (13) | 0.0255 (5) | |
O3 | 0.8062 (2) | 0.0766 (2) | 0.31280 (15) | 0.0368 (6) | |
O4 | 0.9086 (2) | −0.0881 (2) | 0.29473 (14) | 0.0314 (6) | |
O5 | 0.2247 (2) | 0.24750 (18) | 0.71208 (12) | 0.0250 (5) | |
O6 | 0.4361 (2) | 0.1771 (2) | 0.70900 (14) | 0.0316 (6) | |
O7 | 0.5820 (2) | 0.5907 (2) | 0.71313 (14) | 0.0328 (6) | |
O8 | 0.6875 (2) | 0.4331 (2) | 0.68585 (15) | 0.0365 (6) | |
O9 | 0.3411 (3) | 0.1626 (3) | 0.91959 (18) | 0.0579 (9) | |
O10 | 0.1555 (3) | 0.3657 (3) | 1.0354 (2) | 0.0789 (11) | |
Cd1 | 1.21121 (2) | 0.423270 (19) | 0.301290 (13) | 0.02138 (8) | |
Cd2 | 0.29640 (2) | 0.072572 (19) | 0.699760 (13) | 0.02152 (8) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0223 (17) | 0.026 (2) | 0.0197 (18) | −0.0142 (15) | −0.0018 (14) | −0.0031 (15) |
C2 | 0.0220 (16) | 0.0245 (19) | 0.0208 (18) | −0.0121 (15) | 0.0003 (13) | −0.0068 (15) |
C3 | 0.0191 (16) | 0.0215 (18) | 0.0244 (19) | −0.0094 (14) | −0.0017 (13) | −0.0055 (15) |
C4 | 0.0194 (16) | 0.0251 (19) | 0.0222 (18) | −0.0111 (15) | 0.0014 (13) | −0.0072 (15) |
C5 | 0.0295 (18) | 0.0205 (19) | 0.034 (2) | −0.0130 (15) | −0.0003 (15) | −0.0077 (16) |
C6 | 0.0191 (16) | 0.0220 (19) | 0.043 (2) | −0.0065 (15) | −0.0037 (15) | −0.0080 (17) |
C7 | 0.0177 (16) | 0.029 (2) | 0.033 (2) | −0.0121 (15) | −0.0012 (14) | −0.0088 (16) |
C8 | 0.0270 (18) | 0.030 (2) | 0.0190 (18) | −0.0182 (16) | 0.0032 (14) | −0.0064 (15) |
C9 | 0.0217 (16) | 0.0240 (19) | 0.0189 (18) | −0.0119 (15) | −0.0019 (13) | −0.0045 (15) |
C10 | 0.0221 (16) | 0.0220 (19) | 0.0222 (18) | −0.0107 (15) | −0.0035 (14) | −0.0041 (15) |
C11 | 0.0179 (15) | 0.0257 (19) | 0.0217 (18) | −0.0093 (14) | 0.0003 (13) | −0.0079 (15) |
C12 | 0.0197 (16) | 0.0249 (19) | 0.0239 (19) | −0.0121 (15) | 0.0005 (14) | −0.0039 (15) |
C13 | 0.0261 (18) | 0.026 (2) | 0.042 (2) | −0.0121 (16) | 0.0000 (16) | −0.0130 (17) |
C14 | 0.0188 (17) | 0.029 (2) | 0.058 (3) | −0.0078 (16) | 0.0010 (17) | −0.0167 (19) |
C15 | 0.0168 (16) | 0.029 (2) | 0.041 (2) | −0.0121 (15) | −0.0029 (15) | −0.0090 (17) |
C16 | 0.0273 (18) | 0.029 (2) | 0.026 (2) | −0.0181 (16) | −0.0037 (15) | −0.0058 (16) |
C17 | 0.0261 (17) | 0.0254 (19) | 0.0215 (19) | −0.0107 (15) | −0.0012 (14) | −0.0045 (15) |
C18 | 0.0263 (18) | 0.024 (2) | 0.038 (2) | −0.0096 (16) | −0.0056 (16) | −0.0086 (17) |
C19 | 0.0307 (19) | 0.028 (2) | 0.030 (2) | −0.0097 (16) | −0.0062 (16) | −0.0080 (16) |
C20 | 0.0312 (19) | 0.032 (2) | 0.027 (2) | −0.0144 (17) | 0.0033 (16) | −0.0067 (17) |
C21 | 0.0291 (18) | 0.028 (2) | 0.024 (2) | −0.0163 (16) | 0.0077 (15) | −0.0041 (16) |
C22 | 0.0249 (18) | 0.034 (2) | 0.046 (2) | −0.0075 (17) | 0.0018 (17) | −0.0155 (19) |
C23 | 0.034 (2) | 0.031 (2) | 0.037 (2) | −0.0138 (17) | 0.0087 (17) | −0.0142 (17) |
C24 | 0.0301 (19) | 0.029 (2) | 0.023 (2) | −0.0164 (16) | 0.0061 (15) | −0.0005 (16) |
C25 | 0.0242 (18) | 0.033 (2) | 0.050 (3) | −0.0064 (17) | 0.0024 (17) | −0.0140 (19) |
C26 | 0.032 (2) | 0.029 (2) | 0.045 (2) | −0.0126 (17) | 0.0062 (17) | −0.0173 (18) |
C27 | 0.0340 (19) | 0.035 (2) | 0.023 (2) | −0.0162 (17) | 0.0038 (16) | −0.0034 (17) |
C28 | 0.0204 (16) | 0.027 (2) | 0.0252 (19) | −0.0088 (15) | 0.0015 (14) | −0.0076 (16) |
C29 | 0.0235 (17) | 0.027 (2) | 0.034 (2) | −0.0091 (15) | −0.0046 (15) | −0.0111 (17) |
C30 | 0.0290 (18) | 0.027 (2) | 0.025 (2) | −0.0055 (16) | −0.0073 (15) | −0.0100 (16) |
C31 | 0.0281 (18) | 0.026 (2) | 0.0229 (19) | −0.0145 (16) | 0.0007 (15) | −0.0029 (15) |
C32 | 0.039 (2) | 0.029 (2) | 0.030 (2) | −0.0107 (17) | −0.0066 (17) | −0.0114 (17) |
C33 | 0.036 (2) | 0.034 (2) | 0.027 (2) | −0.0106 (18) | −0.0063 (16) | −0.0111 (17) |
C34 | 0.0302 (18) | 0.022 (2) | 0.027 (2) | −0.0065 (16) | 0.0055 (15) | −0.0053 (16) |
C35 | 0.0262 (17) | 0.0218 (19) | 0.0247 (19) | −0.0089 (15) | −0.0005 (14) | −0.0047 (15) |
C36 | 0.0239 (17) | 0.031 (2) | 0.034 (2) | −0.0072 (16) | 0.0075 (15) | −0.0040 (17) |
C44 | 0.035 (2) | 0.066 (3) | 0.044 (3) | −0.020 (2) | −0.011 (2) | 0.023 (2) |
C42 | 0.0269 (18) | 0.0216 (19) | 0.027 (2) | −0.0051 (15) | 0.0029 (15) | −0.0026 (16) |
C43 | 0.033 (2) | 0.062 (3) | 0.055 (3) | −0.021 (2) | −0.008 (2) | 0.016 (2) |
C37 | 0.0257 (18) | 0.027 (2) | 0.036 (2) | −0.0026 (16) | 0.0013 (16) | −0.0007 (17) |
C41 | 0.0301 (19) | 0.024 (2) | 0.033 (2) | −0.0061 (16) | 0.0084 (16) | −0.0009 (17) |
C38 | 0.0317 (18) | 0.025 (2) | 0.0220 (19) | −0.0141 (16) | 0.0008 (15) | −0.0067 (15) |
C39 | 0.0324 (19) | 0.028 (2) | 0.030 (2) | −0.0119 (17) | −0.0014 (16) | −0.0117 (17) |
C40 | 0.0300 (19) | 0.033 (2) | 0.026 (2) | −0.0068 (17) | −0.0057 (16) | −0.0075 (17) |
C45 | 0.046 (3) | 0.072 (4) | 0.039 (3) | −0.010 (3) | −0.007 (2) | −0.024 (2) |
C46 | 0.066 (3) | 0.077 (4) | 0.061 (3) | −0.031 (3) | −0.012 (3) | −0.007 (3) |
C47 | 0.049 (3) | 0.088 (4) | 0.115 (5) | −0.012 (3) | −0.012 (3) | −0.060 (4) |
C48 | 0.068 (3) | 0.051 (3) | 0.066 (3) | −0.016 (3) | −0.016 (3) | −0.022 (3) |
C49 | 0.045 (2) | 0.050 (3) | 0.041 (3) | −0.012 (2) | −0.005 (2) | −0.008 (2) |
C50 | 0.049 (3) | 0.071 (4) | 0.049 (3) | −0.013 (3) | −0.004 (2) | −0.013 (3) |
N1 | 0.0246 (14) | 0.0242 (16) | 0.0280 (17) | −0.0105 (13) | −0.0013 (12) | −0.0067 (13) |
N2 | 0.0244 (14) | 0.0217 (16) | 0.0226 (16) | −0.0079 (12) | −0.0001 (12) | −0.0050 (13) |
N3 | 0.0230 (14) | 0.0234 (16) | 0.0265 (16) | −0.0099 (12) | 0.0024 (12) | −0.0069 (13) |
N4 | 0.0221 (14) | 0.0207 (16) | 0.0233 (16) | −0.0067 (12) | 0.0012 (12) | −0.0061 (13) |
N5 | 0.0268 (15) | 0.0236 (17) | 0.0269 (17) | −0.0103 (13) | −0.0033 (12) | −0.0038 (13) |
N6 | 0.0263 (15) | 0.0243 (16) | 0.0192 (15) | −0.0102 (13) | 0.0019 (12) | −0.0030 (13) |
N7 | 0.0251 (14) | 0.0218 (16) | 0.0274 (17) | −0.0114 (13) | −0.0030 (12) | −0.0040 (13) |
N8 | 0.0242 (14) | 0.0223 (16) | 0.0251 (17) | −0.0068 (13) | 0.0021 (12) | −0.0024 (13) |
N9 | 0.044 (2) | 0.057 (3) | 0.038 (2) | −0.0153 (19) | −0.0092 (16) | −0.0175 (18) |
N10 | 0.042 (2) | 0.039 (2) | 0.039 (2) | −0.0082 (17) | −0.0100 (16) | −0.0088 (16) |
O1 | 0.0246 (13) | 0.0236 (14) | 0.0580 (18) | −0.0090 (11) | −0.0105 (12) | −0.0115 (12) |
O2 | 0.0227 (12) | 0.0281 (14) | 0.0323 (14) | −0.0154 (10) | 0.0022 (10) | −0.0115 (11) |
O3 | 0.0217 (13) | 0.0466 (17) | 0.0551 (18) | −0.0165 (12) | 0.0079 (12) | −0.0305 (14) |
O4 | 0.0252 (13) | 0.0307 (15) | 0.0475 (17) | −0.0179 (11) | −0.0027 (11) | −0.0134 (12) |
O5 | 0.0222 (11) | 0.0271 (14) | 0.0309 (14) | −0.0155 (10) | 0.0016 (10) | −0.0090 (11) |
O6 | 0.0239 (13) | 0.0276 (14) | 0.0487 (17) | −0.0089 (11) | −0.0049 (11) | −0.0164 (12) |
O7 | 0.0269 (13) | 0.0288 (15) | 0.0505 (17) | −0.0145 (11) | −0.0046 (11) | −0.0149 (12) |
O8 | 0.0224 (13) | 0.0459 (17) | 0.0522 (18) | −0.0181 (12) | 0.0090 (12) | −0.0265 (14) |
O9 | 0.0438 (18) | 0.064 (2) | 0.070 (2) | −0.0162 (16) | −0.0054 (16) | −0.0264 (18) |
O10 | 0.066 (2) | 0.073 (3) | 0.113 (3) | −0.041 (2) | 0.001 (2) | −0.031 (2) |
Cd1 | 0.01834 (13) | 0.02126 (15) | 0.02570 (16) | −0.00977 (11) | 0.00102 (10) | −0.00628 (11) |
Cd2 | 0.01866 (13) | 0.02158 (15) | 0.02509 (16) | −0.00998 (11) | 0.00115 (10) | −0.00570 (11) |
C1—O1 | 1.244 (4) | C31—N6 | 1.344 (4) |
C1—O2 | 1.271 (4) | C31—H31 | 0.9500 |
C1—C2 | 1.499 (4) | C32—C33 | 1.358 (5) |
C1—Cd1 | 2.731 (3) | C32—N5 | 1.376 (4) |
C2—C3 | 1.390 (4) | C32—H32 | 0.9500 |
C2—C7 | 1.397 (4) | C33—N6 | 1.367 (4) |
C3—C4 | 1.391 (4) | C33—H33 | 0.9500 |
C3—H3 | 0.9500 | C34—N6 | 1.456 (4) |
C4—C5 | 1.391 (4) | C34—C35 | 1.518 (4) |
C4—C8 | 1.504 (4) | C34—H34A | 0.9900 |
C5—C6 | 1.384 (4) | C34—H34B | 0.9900 |
C5—H5 | 0.9500 | C35—C37 | 1.374 (5) |
C6—C7 | 1.374 (4) | C35—C36 | 1.377 (4) |
C6—H6 | 0.9500 | C36—C37i | 1.384 (5) |
C7—H7 | 0.9500 | C36—H36 | 0.9500 |
C8—O3 | 1.245 (4) | C44—C42 | 1.341 (5) |
C8—O4 | 1.270 (4) | C44—C43ii | 1.384 (5) |
C9—O6 | 1.243 (4) | C44—H44 | 0.9500 |
C9—O5 | 1.270 (4) | C42—C43 | 1.364 (5) |
C9—C10 | 1.505 (4) | C42—C41 | 1.520 (4) |
C9—Cd2 | 2.732 (3) | C43—C44ii | 1.384 (5) |
C10—C15 | 1.390 (4) | C43—H43 | 0.9500 |
C10—C11 | 1.391 (4) | C37—C36i | 1.384 (5) |
C11—C12 | 1.385 (4) | C37—H37 | 0.9500 |
C11—H11 | 0.9500 | C41—N8 | 1.469 (4) |
C12—C13 | 1.392 (4) | C41—H41A | 0.9900 |
C12—C16 | 1.506 (4) | C41—H41B | 0.9900 |
C13—C14 | 1.382 (5) | C38—N7 | 1.317 (4) |
C13—H13 | 0.9500 | C38—N8 | 1.334 (4) |
C14—C15 | 1.382 (5) | C38—H38 | 0.9500 |
C14—H14 | 0.9500 | C39—C40 | 1.347 (5) |
C15—H15 | 0.9500 | C39—N7 | 1.383 (4) |
C16—O8 | 1.243 (4) | C39—H39 | 0.9500 |
C16—O7 | 1.273 (4) | C40—N8 | 1.380 (4) |
C17—N1 | 1.321 (4) | C40—H40 | 0.9500 |
C17—N2 | 1.343 (4) | C45—O9 | 1.235 (5) |
C17—H17 | 0.9500 | C45—N9 | 1.315 (5) |
C18—C19 | 1.357 (5) | C45—H45 | 0.9500 |
C18—N1 | 1.379 (4) | C46—N9 | 1.422 (5) |
C18—H18 | 0.9500 | C46—H46A | 0.9800 |
C19—N2 | 1.365 (4) | C46—H46B | 0.9800 |
C19—H19 | 0.9500 | C46—H46C | 0.9800 |
C20—N2 | 1.479 (4) | C47—N9 | 1.458 (5) |
C20—C21 | 1.507 (5) | C47—H47A | 0.9800 |
C20—H20A | 0.9900 | C47—H47B | 0.9800 |
C20—H20B | 0.9900 | C47—H47C | 0.9800 |
C21—C22 | 1.375 (5) | C48—O10 | 1.231 (6) |
C21—C26 | 1.384 (5) | C48—N10 | 1.317 (5) |
C22—C23 | 1.381 (5) | C48—H48 | 0.9500 |
C22—H22 | 0.9500 | C49—N10 | 1.455 (5) |
C23—C24 | 1.384 (5) | C49—H49A | 0.9800 |
C23—H23 | 0.9500 | C49—H49B | 0.9800 |
C24—C25 | 1.384 (5) | C49—H49C | 0.9800 |
C24—C27 | 1.514 (5) | C50—N10 | 1.442 (5) |
C25—C26 | 1.380 (5) | C50—H50A | 0.9800 |
C25—H25 | 0.9500 | C50—H50B | 0.9800 |
C26—H26 | 0.9500 | C50—H50C | 0.9800 |
C27—N4 | 1.471 (4) | N1—Cd1 | 2.208 (3) |
C27—H27A | 0.9900 | N3—Cd2 | 2.206 (3) |
C27—H27B | 0.9900 | N5—Cd1 | 2.213 (3) |
C28—N3 | 1.328 (4) | N7—Cd2 | 2.212 (3) |
C28—N4 | 1.340 (4) | O1—Cd1 | 2.517 (2) |
C28—H28 | 0.9500 | O2—Cd1 | 2.283 (2) |
C29—C30 | 1.351 (5) | O4—Cd2iii | 2.217 (2) |
C29—N3 | 1.378 (4) | O5—Cd2 | 2.277 (2) |
C29—H29 | 0.9500 | O6—Cd2 | 2.519 (2) |
C30—N4 | 1.374 (4) | O7—Cd1iv | 2.232 (2) |
C30—H30 | 0.9500 | Cd1—O7iv | 2.232 (2) |
C31—N5 | 1.321 (4) | Cd2—O4iii | 2.217 (2) |
O1—C1—O2 | 122.9 (3) | C42—C44—C43ii | 122.0 (4) |
O1—C1—C2 | 120.1 (3) | C42—C44—H44 | 119.0 |
O2—C1—C2 | 117.1 (3) | C43ii—C44—H44 | 119.0 |
O1—C1—Cd1 | 66.82 (18) | C44—C42—C43 | 117.9 (3) |
O2—C1—Cd1 | 56.19 (16) | C44—C42—C41 | 121.2 (3) |
C2—C1—Cd1 | 171.8 (2) | C43—C42—C41 | 120.9 (3) |
C3—C2—C7 | 118.8 (3) | C42—C43—C44ii | 120.1 (4) |
C3—C2—C1 | 120.6 (3) | C42—C43—H43 | 120.0 |
C7—C2—C1 | 120.5 (3) | C44ii—C43—H43 | 120.0 |
C2—C3—C4 | 120.9 (3) | C35—C37—C36i | 120.9 (3) |
C2—C3—H3 | 119.6 | C35—C37—H37 | 119.6 |
C4—C3—H3 | 119.6 | C36i—C37—H37 | 119.6 |
C3—C4—C5 | 119.1 (3) | N8—C41—C42 | 112.2 (3) |
C3—C4—C8 | 120.7 (3) | N8—C41—H41A | 109.2 |
C5—C4—C8 | 120.2 (3) | C42—C41—H41A | 109.2 |
C6—C5—C4 | 120.4 (3) | N8—C41—H41B | 109.2 |
C6—C5—H5 | 119.8 | C42—C41—H41B | 109.2 |
C4—C5—H5 | 119.8 | H41A—C41—H41B | 107.9 |
C7—C6—C5 | 120.2 (3) | N7—C38—N8 | 111.8 (3) |
C7—C6—H6 | 119.9 | N7—C38—H38 | 124.1 |
C5—C6—H6 | 119.9 | N8—C38—H38 | 124.1 |
C6—C7—C2 | 120.6 (3) | C40—C39—N7 | 109.6 (3) |
C6—C7—H7 | 119.7 | C40—C39—H39 | 125.2 |
C2—C7—H7 | 119.7 | N7—C39—H39 | 125.2 |
O3—C8—O4 | 122.9 (3) | C39—C40—N8 | 106.1 (3) |
O3—C8—C4 | 120.6 (3) | C39—C40—H40 | 126.9 |
O4—C8—C4 | 116.4 (3) | N8—C40—H40 | 126.9 |
O6—C9—O5 | 122.7 (3) | O9—C45—N9 | 125.2 (5) |
O6—C9—C10 | 119.8 (3) | O9—C45—H45 | 117.4 |
O5—C9—C10 | 117.5 (3) | N9—C45—H45 | 117.4 |
O6—C9—Cd2 | 66.90 (18) | N9—C46—H46A | 109.5 |
O5—C9—Cd2 | 55.89 (16) | N9—C46—H46B | 109.5 |
C10—C9—Cd2 | 172.5 (2) | H46A—C46—H46B | 109.5 |
C15—C10—C11 | 119.1 (3) | N9—C46—H46C | 109.5 |
C15—C10—C9 | 120.1 (3) | H46A—C46—H46C | 109.5 |
C11—C10—C9 | 120.8 (3) | H46B—C46—H46C | 109.5 |
C12—C11—C10 | 120.6 (3) | N9—C47—H47A | 109.5 |
C12—C11—H11 | 119.7 | N9—C47—H47B | 109.5 |
C10—C11—H11 | 119.7 | H47A—C47—H47B | 109.5 |
C11—C12—C13 | 119.5 (3) | N9—C47—H47C | 109.5 |
C11—C12—C16 | 120.4 (3) | H47A—C47—H47C | 109.5 |
C13—C12—C16 | 120.1 (3) | H47B—C47—H47C | 109.5 |
C14—C13—C12 | 120.2 (3) | O10—C48—N10 | 125.7 (5) |
C14—C13—H13 | 119.9 | O10—C48—H48 | 117.2 |
C12—C13—H13 | 119.9 | N10—C48—H48 | 117.2 |
C15—C14—C13 | 119.9 (3) | N10—C49—H49A | 109.5 |
C15—C14—H14 | 120.0 | N10—C49—H49B | 109.5 |
C13—C14—H14 | 120.0 | H49A—C49—H49B | 109.5 |
C14—C15—C10 | 120.6 (3) | N10—C49—H49C | 109.5 |
C14—C15—H15 | 119.7 | H49A—C49—H49C | 109.5 |
C10—C15—H15 | 119.7 | H49B—C49—H49C | 109.5 |
O8—C16—O7 | 122.9 (3) | N10—C50—H50A | 109.5 |
O8—C16—C12 | 120.9 (3) | N10—C50—H50B | 109.5 |
O7—C16—C12 | 116.1 (3) | H50A—C50—H50B | 109.5 |
N1—C17—N2 | 110.9 (3) | N10—C50—H50C | 109.5 |
N1—C17—H17 | 124.6 | H50A—C50—H50C | 109.5 |
N2—C17—H17 | 124.6 | H50B—C50—H50C | 109.5 |
C19—C18—N1 | 109.3 (3) | C17—N1—C18 | 105.9 (3) |
C19—C18—H18 | 125.4 | C17—N1—Cd1 | 123.9 (2) |
N1—C18—H18 | 125.4 | C18—N1—Cd1 | 129.0 (2) |
C18—C19—N2 | 106.3 (3) | C17—N2—C19 | 107.8 (3) |
C18—C19—H19 | 126.9 | C17—N2—C20 | 128.4 (3) |
N2—C19—H19 | 126.9 | C19—N2—C20 | 123.8 (3) |
N2—C20—C21 | 112.5 (3) | C28—N3—C29 | 105.6 (3) |
N2—C20—H20A | 109.1 | C28—N3—Cd2 | 124.2 (2) |
C21—C20—H20A | 109.1 | C29—N3—Cd2 | 129.0 (2) |
N2—C20—H20B | 109.1 | C28—N4—C30 | 107.1 (3) |
C21—C20—H20B | 109.1 | C28—N4—C27 | 128.6 (3) |
H20A—C20—H20B | 107.8 | C30—N4—C27 | 124.2 (3) |
C22—C21—C26 | 118.1 (3) | C31—N5—C32 | 106.1 (3) |
C22—C21—C20 | 121.9 (3) | C31—N5—Cd1 | 124.8 (2) |
C26—C21—C20 | 119.9 (3) | C32—N5—Cd1 | 127.3 (2) |
C21—C22—C23 | 121.5 (3) | C31—N6—C33 | 107.1 (3) |
C21—C22—H22 | 119.3 | C31—N6—C34 | 125.9 (3) |
C23—C22—H22 | 119.3 | C33—N6—C34 | 126.9 (3) |
C22—C23—C24 | 120.4 (4) | C38—N7—C39 | 105.3 (3) |
C22—C23—H23 | 119.8 | C38—N7—Cd2 | 126.9 (2) |
C24—C23—H23 | 119.8 | C39—N7—Cd2 | 126.5 (2) |
C25—C24—C23 | 118.2 (4) | C38—N8—C40 | 107.1 (3) |
C25—C24—C27 | 121.7 (3) | C38—N8—C41 | 126.7 (3) |
C23—C24—C27 | 120.0 (3) | C40—N8—C41 | 126.1 (3) |
C26—C25—C24 | 121.0 (3) | C45—N9—C46 | 124.1 (4) |
C26—C25—H25 | 119.5 | C45—N9—C47 | 119.6 (4) |
C24—C25—H25 | 119.5 | C46—N9—C47 | 116.3 (4) |
C25—C26—C21 | 120.7 (4) | C48—N10—C50 | 121.7 (4) |
C25—C26—H26 | 119.6 | C48—N10—C49 | 120.1 (4) |
C21—C26—H26 | 119.6 | C50—N10—C49 | 118.3 (4) |
N4—C27—C24 | 112.7 (3) | C1—O1—Cd1 | 86.14 (19) |
N4—C27—H27A | 109.0 | C1—O2—Cd1 | 96.3 (2) |
C24—C27—H27A | 109.0 | C8—O4—Cd2iii | 104.9 (2) |
N4—C27—H27B | 109.0 | C9—O5—Cd2 | 96.6 (2) |
C24—C27—H27B | 109.0 | C9—O6—Cd2 | 86.10 (19) |
H27A—C27—H27B | 107.8 | C16—O7—Cd1iv | 102.0 (2) |
N3—C28—N4 | 111.2 (3) | N1—Cd1—N5 | 120.05 (10) |
N3—C28—H28 | 124.4 | N1—Cd1—O7iv | 113.90 (9) |
N4—C28—H28 | 124.4 | N5—Cd1—O7iv | 108.45 (9) |
C30—C29—N3 | 109.4 (3) | N1—Cd1—O2 | 103.81 (9) |
C30—C29—H29 | 125.3 | N5—Cd1—O2 | 119.59 (9) |
N3—C29—H29 | 125.3 | O7iv—Cd1—O2 | 86.36 (8) |
C29—C30—N4 | 106.6 (3) | N1—Cd1—O1 | 85.77 (9) |
C29—C30—H30 | 126.7 | N5—Cd1—O1 | 87.77 (9) |
N4—C30—H30 | 126.7 | O7iv—Cd1—O1 | 140.15 (8) |
N5—C31—N6 | 111.1 (3) | O2—Cd1—O1 | 54.54 (7) |
N5—C31—H31 | 124.4 | N1—Cd1—C1 | 94.16 (10) |
N6—C31—H31 | 124.4 | N5—Cd1—C1 | 105.59 (10) |
C33—C32—N5 | 108.9 (3) | O7iv—Cd1—C1 | 113.76 (9) |
C33—C32—H32 | 125.6 | O2—Cd1—C1 | 27.55 (8) |
N5—C32—H32 | 125.6 | O1—Cd1—C1 | 27.04 (8) |
C32—C33—N6 | 106.8 (3) | N3—Cd2—N7 | 120.66 (10) |
C32—C33—H33 | 126.6 | N3—Cd2—O4iii | 109.82 (9) |
N6—C33—H33 | 126.6 | N7—Cd2—O4iii | 111.39 (9) |
N6—C34—C35 | 113.0 (3) | N3—Cd2—O5 | 104.62 (9) |
N6—C34—H34A | 109.0 | N7—Cd2—O5 | 118.63 (9) |
C35—C34—H34A | 109.0 | O4iii—Cd2—O5 | 86.42 (8) |
N6—C34—H34B | 109.0 | N3—Cd2—O6 | 85.43 (9) |
C35—C34—H34B | 109.0 | N7—Cd2—O6 | 88.45 (9) |
H34A—C34—H34B | 107.8 | O4iii—Cd2—O6 | 140.80 (8) |
C37—C35—C36 | 118.3 (3) | O5—Cd2—O6 | 54.46 (7) |
C37—C35—C34 | 123.5 (3) | N3—Cd2—C9 | 94.51 (10) |
C36—C35—C34 | 118.2 (3) | N7—Cd2—C9 | 105.43 (10) |
C35—C36—C37i | 120.8 (3) | O4iii—Cd2—C9 | 113.93 (9) |
C35—C36—H36 | 119.6 | O5—Cd2—C9 | 27.51 (8) |
C37i—C36—H36 | 119.6 | O6—Cd2—C9 | 26.99 (8) |
O1—C1—C2—C3 | −4.8 (5) | N7—C38—N8—C40 | −0.3 (4) |
O2—C1—C2—C3 | 174.7 (3) | N7—C38—N8—C41 | −177.1 (3) |
Cd1—C1—C2—C3 | 141.5 (15) | C39—C40—N8—C38 | 0.2 (4) |
O1—C1—C2—C7 | 173.4 (3) | C39—C40—N8—C41 | 177.0 (3) |
O2—C1—C2—C7 | −7.1 (5) | C42—C41—N8—C38 | −107.6 (4) |
Cd1—C1—C2—C7 | −40.3 (18) | C42—C41—N8—C40 | 76.2 (4) |
C7—C2—C3—C4 | −1.8 (5) | O9—C45—N9—C46 | −178.2 (4) |
C1—C2—C3—C4 | 176.4 (3) | O9—C45—N9—C47 | 1.0 (7) |
C2—C3—C4—C5 | 0.2 (5) | O10—C48—N10—C50 | −179.5 (5) |
C2—C3—C4—C8 | −178.7 (3) | O10—C48—N10—C49 | −1.6 (7) |
C3—C4—C5—C6 | 1.2 (5) | O2—C1—O1—Cd1 | −4.4 (3) |
C8—C4—C5—C6 | −179.9 (3) | C2—C1—O1—Cd1 | 175.1 (3) |
C4—C5—C6—C7 | −1.0 (5) | O1—C1—O2—Cd1 | 4.9 (3) |
C5—C6—C7—C2 | −0.7 (5) | C2—C1—O2—Cd1 | −174.6 (2) |
C3—C2—C7—C6 | 2.1 (5) | O3—C8—O4—Cd2iii | 1.8 (4) |
C1—C2—C7—C6 | −176.1 (3) | C4—C8—O4—Cd2iii | −177.0 (2) |
C3—C4—C8—O3 | −3.0 (5) | O6—C9—O5—Cd2 | −4.4 (3) |
C5—C4—C8—O3 | 178.1 (3) | C10—C9—O5—Cd2 | 175.8 (2) |
C3—C4—C8—O4 | 175.8 (3) | O5—C9—O6—Cd2 | 4.0 (3) |
C5—C4—C8—O4 | −3.1 (5) | C10—C9—O6—Cd2 | −176.3 (3) |
O6—C9—C10—C15 | −173.5 (3) | O8—C16—O7—Cd1iv | −1.5 (4) |
O5—C9—C10—C15 | 6.3 (5) | C12—C16—O7—Cd1iv | 178.6 (2) |
Cd2—C9—C10—C15 | 33.8 (19) | C17—N1—Cd1—N5 | 72.8 (3) |
O6—C9—C10—C11 | 5.2 (5) | C18—N1—Cd1—N5 | −121.5 (3) |
O5—C9—C10—C11 | −175.0 (3) | C17—N1—Cd1—O7iv | −156.2 (2) |
Cd2—C9—C10—C11 | −147.5 (16) | C18—N1—Cd1—O7iv | 9.6 (3) |
C15—C10—C11—C12 | 1.5 (5) | C17—N1—Cd1—O2 | −64.0 (3) |
C9—C10—C11—C12 | −177.2 (3) | C18—N1—Cd1—O2 | 101.7 (3) |
C10—C11—C12—C13 | −0.2 (5) | C17—N1—Cd1—O1 | −12.2 (3) |
C10—C11—C12—C16 | 179.9 (3) | C18—N1—Cd1—O1 | 153.6 (3) |
C11—C12—C13—C14 | −1.2 (5) | C17—N1—Cd1—C1 | −37.9 (3) |
C16—C12—C13—C14 | 178.7 (3) | C18—N1—Cd1—C1 | 127.9 (3) |
C12—C13—C14—C15 | 1.2 (6) | C31—N5—Cd1—N1 | 49.6 (3) |
C13—C14—C15—C10 | 0.1 (6) | C32—N5—Cd1—N1 | −112.7 (3) |
C11—C10—C15—C14 | −1.5 (5) | C31—N5—Cd1—O7iv | −83.7 (3) |
C9—C10—C15—C14 | 177.3 (3) | C32—N5—Cd1—O7iv | 113.9 (3) |
C11—C12—C16—O8 | 5.7 (5) | C31—N5—Cd1—O2 | 179.8 (2) |
C13—C12—C16—O8 | −174.2 (3) | C32—N5—Cd1—O2 | 17.5 (3) |
C11—C12—C16—O7 | −174.4 (3) | C31—N5—Cd1—O1 | 133.4 (3) |
C13—C12—C16—O7 | 5.7 (5) | C32—N5—Cd1—O1 | −28.9 (3) |
N1—C18—C19—N2 | 0.0 (4) | C31—N5—Cd1—C1 | 154.0 (2) |
N2—C20—C21—C22 | 66.8 (4) | C32—N5—Cd1—C1 | −8.3 (3) |
N2—C20—C21—C26 | −115.0 (4) | C1—O2—Cd1—N1 | 72.0 (2) |
C26—C21—C22—C23 | 0.4 (5) | C1—O2—Cd1—N5 | −65.1 (2) |
C20—C21—C22—C23 | 178.7 (3) | C1—O2—Cd1—O7iv | −174.3 (2) |
C21—C22—C23—C24 | −0.7 (6) | C1—O2—Cd1—O1 | −2.48 (18) |
C22—C23—C24—C25 | 0.6 (5) | C1—O1—Cd1—N1 | −107.7 (2) |
C22—C23—C24—C27 | 178.9 (3) | C1—O1—Cd1—N5 | 131.9 (2) |
C23—C24—C25—C26 | −0.3 (5) | C1—O1—Cd1—O7iv | 15.3 (3) |
C27—C24—C25—C26 | −178.5 (3) | C1—O1—Cd1—O2 | 2.53 (18) |
C24—C25—C26—C21 | 0.0 (6) | O1—C1—Cd1—N1 | 72.2 (2) |
C22—C21—C26—C25 | 0.0 (5) | O2—C1—Cd1—N1 | −112.22 (19) |
C20—C21—C26—C25 | −178.3 (3) | C2—C1—Cd1—N1 | −76.3 (16) |
C25—C24—C27—N4 | −68.2 (4) | O1—C1—Cd1—N5 | −50.5 (2) |
C23—C24—C27—N4 | 113.5 (4) | O2—C1—Cd1—N5 | 125.00 (19) |
N3—C29—C30—N4 | −0.1 (4) | C2—C1—Cd1—N5 | 160.9 (16) |
N5—C32—C33—N6 | 0.1 (4) | O1—C1—Cd1—O7iv | −169.35 (18) |
N6—C34—C35—C37 | −20.1 (5) | O2—C1—Cd1—O7iv | 6.2 (2) |
N6—C34—C35—C36 | 161.8 (3) | C2—C1—Cd1—O7iv | 42.1 (16) |
C37—C35—C36—C37i | 0.0 (6) | O1—C1—Cd1—O2 | −175.5 (3) |
C34—C35—C36—C37i | 178.2 (3) | C2—C1—Cd1—O2 | 35.9 (15) |
C43ii—C44—C42—C43 | −0.7 (8) | O2—C1—Cd1—O1 | 175.5 (3) |
C43ii—C44—C42—C41 | 177.7 (4) | C2—C1—Cd1—O1 | −148.5 (17) |
C44—C42—C43—C44ii | 0.7 (8) | C28—N3—Cd2—N7 | −74.1 (3) |
C41—C42—C43—C44ii | −177.7 (4) | C29—N3—Cd2—N7 | 120.3 (3) |
C36—C35—C37—C36i | 0.0 (6) | C28—N3—Cd2—O4iii | 154.3 (2) |
C34—C35—C37—C36i | −178.1 (4) | C29—N3—Cd2—O4iii | −11.4 (3) |
C44—C42—C41—N8 | 58.7 (5) | C28—N3—Cd2—O5 | 62.8 (3) |
C43—C42—C41—N8 | −122.9 (4) | C29—N3—Cd2—O5 | −102.8 (3) |
N7—C39—C40—N8 | 0.0 (4) | C28—N3—Cd2—O6 | 11.4 (3) |
N2—C17—N1—C18 | 0.2 (4) | C29—N3—Cd2—O6 | −154.3 (3) |
N2—C17—N1—Cd1 | 168.7 (2) | C28—N3—Cd2—C9 | 36.9 (3) |
C19—C18—N1—C17 | −0.1 (4) | C29—N3—Cd2—C9 | −128.8 (3) |
C19—C18—N1—Cd1 | −167.8 (2) | C38—N7—Cd2—N3 | −46.5 (3) |
N1—C17—N2—C19 | −0.1 (4) | C39—N7—Cd2—N3 | 118.9 (3) |
N1—C17—N2—C20 | 178.1 (3) | C38—N7—Cd2—O4iii | 84.5 (3) |
C18—C19—N2—C17 | 0.1 (4) | C39—N7—Cd2—O4iii | −110.1 (3) |
C18—C19—N2—C20 | −178.3 (3) | C38—N7—Cd2—O5 | −177.6 (2) |
C21—C20—N2—C17 | 10.4 (5) | C39—N7—Cd2—O5 | −12.2 (3) |
C21—C20—N2—C19 | −171.6 (3) | C38—N7—Cd2—O6 | −130.2 (3) |
N4—C28—N3—C29 | 0.1 (4) | C39—N7—Cd2—O6 | 35.1 (3) |
N4—C28—N3—Cd2 | −168.33 (19) | C38—N7—Cd2—C9 | −151.5 (3) |
C30—C29—N3—C28 | 0.0 (4) | C39—N7—Cd2—C9 | 13.9 (3) |
C30—C29—N3—Cd2 | 167.7 (2) | C9—O5—Cd2—N3 | −71.0 (2) |
N3—C28—N4—C30 | −0.2 (4) | C9—O5—Cd2—N7 | 66.9 (2) |
N3—C28—N4—C27 | −177.9 (3) | C9—O5—Cd2—O4iii | 179.39 (19) |
C29—C30—N4—C28 | 0.2 (4) | C9—O5—Cd2—O6 | 2.24 (17) |
C29—C30—N4—C27 | 178.0 (3) | C9—O6—Cd2—N3 | 109.3 (2) |
C24—C27—N4—C28 | −9.2 (5) | C9—O6—Cd2—N7 | −129.7 (2) |
C24—C27—N4—C30 | 173.5 (3) | C9—O6—Cd2—O4iii | −6.8 (3) |
N6—C31—N5—C32 | −0.4 (4) | C9—O6—Cd2—O5 | −2.28 (18) |
N6—C31—N5—Cd1 | −165.9 (2) | O6—C9—Cd2—N3 | −70.66 (19) |
C33—C32—N5—C31 | 0.2 (4) | O5—C9—Cd2—N3 | 113.36 (19) |
C33—C32—N5—Cd1 | 165.2 (2) | C10—C9—Cd2—N3 | 83.7 (17) |
N5—C31—N6—C33 | 0.5 (4) | O6—C9—Cd2—N7 | 52.9 (2) |
N5—C31—N6—C34 | 178.0 (3) | O5—C9—Cd2—N7 | −123.11 (18) |
C32—C33—N6—C31 | −0.3 (4) | C10—C9—Cd2—N7 | −152.8 (17) |
C32—C33—N6—C34 | −177.9 (3) | O6—C9—Cd2—O4iii | 175.31 (18) |
C35—C34—N6—C31 | 108.9 (4) | O5—C9—Cd2—O4iii | −0.7 (2) |
C35—C34—N6—C33 | −74.0 (4) | C10—C9—Cd2—O4iii | −30.3 (18) |
N8—C38—N7—C39 | 0.3 (4) | O6—C9—Cd2—O5 | 176.0 (3) |
N8—C38—N7—Cd2 | 168.1 (2) | C10—C9—Cd2—O5 | −29.7 (17) |
C40—C39—N7—C38 | −0.1 (4) | O5—C9—Cd2—O6 | −176.0 (3) |
C40—C39—N7—Cd2 | −168.0 (2) | C10—C9—Cd2—O6 | 154.3 (19) |
Symmetry codes: (i) −x+2, −y+2, −z; (ii) −x+1, −y−1, −z+2; (iii) −x+1, −y, −z+1; (iv) −x+2, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | [Cd(C8H4O4)(C14H14N4)]·C3H7NO |
Mr | 587.90 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 185 |
a, b, c (Å) | 11.2088 (4), 13.4710 (5), 18.9133 (7) |
α, β, γ (°) | 69.648 (1), 80.124 (1), 68.521 (1) |
V (Å3) | 2488.37 (16) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.92 |
Crystal size (mm) | 0.26 × 0.23 × 0.13 |
Data collection | |
Diffractometer | Bruker APEXII CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2007) |
Tmin, Tmax | 0.795, 0.889 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13952, 9746, 6383 |
Rint | 0.017 |
(sin θ/λ)max (Å−1) | 0.619 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.034, 0.095, 1.05 |
No. of reflections | 9746 |
No. of parameters | 649 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.61, −0.51 |
Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), XP in SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1999).
Acknowledgements
The authors thank Jilin University for supporting this work.
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Studies of metal-organic coordination polymers (MOCPs) are of considerable interest due to their intrinsically interesting structures and fascinating network topologies (Batten et al., 1998), and potential applications in storage (Chen et al., 2011), catalysis (Farrusseng et al., 2009), molecular magnetism (Kurmoo, 2009), recognition (Pramanik et al., 2011), and photoluminescence (Wong et al., 2006). An important motivation for this field is the rational design and preparation of crystalline solid material with peculiar topology and desired functions. The design possibilities of organic ligands and the coordination tendencies of metal ions have led to a large number of novel structural features quite often endowed with unique properties. Aromatic multi-acids are good connectors in constructed excellent porous coordination polymers due to their rigidity in conformation and various coordination modes. In particular, the combination of multicarboxylate anions with N-donor auxiliary ligands is a good choice for the construction of novel topology and networks.
In the present case, we used the benzene-1,3-dicarboxylic acid (m-H2bdc) as anionic ligand and 1,4-bis(imidazol-l-yl-methyl)benzene (bix) as ancillary ligand to construct a novel two-dimensional coordination polymer.
The structure shows pseudo-symmetry, in which the atoms in the main framework fulfill the pseudo-C centring and the DMF molecules break this pseudo-symmetry. The asymmetric unit contains two crystallographically independent Cd(II) ions, two m-bdc2- ligands, one and two halves bix ligands, and two lattice DMF molecules (Fig. 1). Cd1 and Cd2 have the same coordination environment. They are five-coordinated by three oxygen atoms from two different m-bdc2- ligands and two nitrogen atoms from two different bix ligands. The distortion parameters τ5 of 0.335 for both Cd1 and Cd2 indicate that the coordination environment corresponds to a distorted square pyramid; expected values are τ = 0 for a square pyramid and τ = 1 for an ideal trigonal bipyramid (Addison et al., 1984).
As shown in Fig. 2, The m-bdc2- ligands adopt a chelate-monodentate coordination mode, connect neighboring Cd ions into a zigzag chain. Adjacent chains are further cross-linked by bix ligands, giving rise to a 2-D puckered sheet with intragrid Cd···Cd separations of 10.245 (5) × 12.979 (5) Å and 10.193 (5) × 15.336 (5) Å across each m-bdc2- ligand and bix ligand in the trans-conformation, respectively. Thus, the each Cd(II) is connected to four neighboring Cd atoms through two m-bdc2- anions and two bix ligands to give rise to the final non-interpenetrating uninodal two-dimensional layer with sql topology (Blatov et al., 2010). Furthermore, the adjacent two-dimensional layers stack in an ···AAA··· sequence, in which π-π interactions between the imidazol rings have a stabilizing effect [the cog(N1,N2,C17,C18,C19)···cog(N1,N2,C17,C18,C19)i and cog(N3,N4,C28,C29,C30)···cog(N3,N4,C28,C29,C30)ii distances are 3.517 Å and 3.478 Å, respectively; symmetry operators: (i) 2 - x,1 - y,1 - z, and (ii) 1 - x,-y,1 - z].