Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270109029084/gd3296sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270109029084/gd3296Isup2.hkl |
CCDC reference: 749687
Zinc chloride (0.068 g, 0.5 mmol), naphthalene-1,4-dicarboxylatic acid (0.108 g, 0.5 mmol) and 1,4-bis(imidazol-1-ylmethyl)benzene (0.119 g, 0.5 mmol) were placed in water (12 ml), and triethylamine was added until the pH value of the solution was 5.8. The solution was heated in a 25 ml Teflon-lined stainless-steel autoclave at 450 K for 5 d. The autoclave was allowed to cool to room temperature over several hours. Colourless blocks were isolated in about 42% yield.
The H atoms were treated as riding atoms in geometrically idealized positions with C—H distances of 0.93 and 0.97 Å, and Uiso(H) values of 1.2Ueq(C).
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2009).
[Zn(C12H6O4)(C14H14N4)] | Z = 4 |
Mr = 517.83 | F(000) = 1064 |
Triclinic, P1 | Dx = 1.529 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.4112 (5) Å | Cell parameters from 9159 reflections |
b = 11.5745 (5) Å | θ = 3.0–26.4° |
c = 19.1907 (9) Å | µ = 1.13 mm−1 |
α = 96.319 (4)° | T = 293 K |
β = 93.869 (5)° | Block, colourless |
γ = 100.628 (4)° | 0.33 × 0.27 × 0.22 mm |
V = 2249.95 (18) Å3 |
Bruker APEX diffractometer | 9159 independent reflections |
Radiation source: sealed tube | 4749 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.051 |
ϕ and ω scans | θmax = 26.4°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −10→12 |
Tmin = 0.680, Tmax = 0.775 | k = −11→14 |
22060 measured reflections | l = −23→19 |
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)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.096 | H-atom parameters constrained |
S = 0.83 | w = 1/[σ2(Fo2) + (0.0401P)2] where P = (Fo2 + 2Fc2)/3 |
9159 reflections | (Δ/σ)max = 0.001 |
631 parameters | Δρmax = 0.74 e Å−3 |
0 restraints | Δρmin = −0.44 e Å−3 |
[Zn(C12H6O4)(C14H14N4)] | γ = 100.628 (4)° |
Mr = 517.83 | V = 2249.95 (18) Å3 |
Triclinic, P1 | Z = 4 |
a = 10.4112 (5) Å | Mo Kα radiation |
b = 11.5745 (5) Å | µ = 1.13 mm−1 |
c = 19.1907 (9) Å | T = 293 K |
α = 96.319 (4)° | 0.33 × 0.27 × 0.22 mm |
β = 93.869 (5)° |
Bruker APEX diffractometer | 9159 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 4749 reflections with I > 2σ(I) |
Tmin = 0.680, Tmax = 0.775 | Rint = 0.051 |
22060 measured reflections |
R[F2 > 2σ(F2)] = 0.046 | 0 restraints |
wR(F2) = 0.096 | H-atom parameters constrained |
S = 0.83 | Δρmax = 0.74 e Å−3 |
9159 reflections | Δρmin = −0.44 e Å−3 |
631 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 | 0.2626 (4) | 0.3646 (4) | 0.5233 (2) | 0.0351 (10) | |
C2 | 0.2869 (3) | 0.3098 (3) | 0.45137 (19) | 0.0302 (9) | |
C3 | 0.3643 (4) | 0.3798 (4) | 0.4111 (2) | 0.0418 (11) | |
H3 | 0.4072 | 0.4553 | 0.4305 | 0.050* | |
C4 | 0.3796 (4) | 0.3392 (4) | 0.3412 (2) | 0.0412 (11) | |
H4 | 0.4352 | 0.3871 | 0.3155 | 0.049* | |
C5 | 0.3147 (4) | 0.2308 (4) | 0.31005 (19) | 0.0338 (10) | |
C6 | 0.3308 (5) | 0.1920 (4) | 0.2336 (2) | 0.0372 (10) | |
C7 | 0.2391 (4) | 0.1540 (3) | 0.35079 (19) | 0.0321 (9) | |
C8 | 0.1765 (4) | 0.0361 (4) | 0.3232 (2) | 0.0481 (11) | |
H8 | 0.1796 | 0.0108 | 0.2758 | 0.058* | |
C9 | 0.1127 (4) | −0.0403 (4) | 0.3637 (2) | 0.0514 (12) | |
H9 | 0.0715 | −0.1162 | 0.3439 | 0.062* | |
C10 | 0.1090 (4) | −0.0044 (4) | 0.4353 (2) | 0.0467 (11) | |
H10 | 0.0698 | −0.0582 | 0.4638 | 0.056* | |
C11 | 0.1621 (4) | 0.1084 (4) | 0.4638 (2) | 0.0376 (10) | |
H11 | 0.1555 | 0.1312 | 0.5112 | 0.045* | |
C12 | 0.2271 (3) | 0.1920 (3) | 0.42316 (19) | 0.0308 (9) | |
C13 | 0.3942 (4) | 0.2548 (4) | 0.02233 (19) | 0.0308 (9) | |
C14 | 0.3324 (3) | 0.2869 (3) | −0.04431 (18) | 0.0276 (9) | |
C15 | 0.4038 (4) | 0.3724 (4) | −0.0767 (2) | 0.0378 (10) | |
H15 | 0.4835 | 0.4147 | −0.0547 | 0.045* | |
C16 | 0.3590 (4) | 0.3981 (4) | −0.1435 (2) | 0.0473 (11) | |
H16 | 0.4086 | 0.4586 | −0.1640 | 0.057* | |
C17 | 0.2454 (4) | 0.3362 (4) | −0.1782 (2) | 0.0396 (11) | |
C18 | 0.2046 (5) | 0.3659 (6) | −0.2510 (3) | 0.0648 (16) | |
C19 | 0.1625 (4) | 0.2497 (3) | −0.14372 (19) | 0.0301 (9) | |
C20 | 0.0360 (4) | 0.1912 (4) | −0.1743 (2) | 0.0457 (12) | |
H20 | 0.0093 | 0.2008 | −0.2202 | 0.055* | |
C21 | −0.0468 (4) | 0.1210 (4) | −0.1372 (2) | 0.0496 (12) | |
H21 | −0.1293 | 0.0828 | −0.1577 | 0.059* | |
C22 | −0.0072 (4) | 0.1068 (4) | −0.0683 (2) | 0.0441 (11) | |
H22 | −0.0650 | 0.0616 | −0.0424 | 0.053* | |
C23 | 0.1147 (4) | 0.1582 (3) | −0.0386 (2) | 0.0346 (10) | |
H23 | 0.1395 | 0.1465 | 0.0071 | 0.042* | |
C24 | 0.2049 (3) | 0.2290 (3) | −0.07573 (19) | 0.0273 (9) | |
C25 | 0.7383 (4) | 0.2540 (3) | 0.15535 (19) | 0.0290 (9) | |
H25 | 0.7109 | 0.3239 | 0.1704 | 0.035* | |
C26 | 0.7387 (4) | 0.0760 (3) | 0.11086 (19) | 0.0338 (10) | |
H26 | 0.7104 | −0.0013 | 0.0891 | 0.041* | |
C27 | 0.8634 (4) | 0.1259 (4) | 0.1338 (2) | 0.0373 (10) | |
H27 | 0.9363 | 0.0903 | 0.1309 | 0.045* | |
C28 | 0.9778 (4) | 0.3254 (4) | 0.1959 (2) | 0.0395 (10) | |
H28A | 1.0411 | 0.2827 | 0.2150 | 0.047* | |
H28B | 0.9510 | 0.3735 | 0.2349 | 0.047* | |
C29 | 1.0433 (4) | 0.4059 (3) | 0.1467 (2) | 0.0320 (9) | |
C30 | 0.9818 (4) | 0.4899 (4) | 0.1200 (2) | 0.0363 (10) | |
H30 | 0.8955 | 0.4916 | 0.1290 | 0.044* | |
C31 | 1.0448 (4) | 0.5704 (3) | 0.0808 (2) | 0.0350 (10) | |
H31 | 1.0012 | 0.6258 | 0.0633 | 0.042* | |
C32 | 1.1730 (4) | 0.5699 (3) | 0.06681 (19) | 0.0318 (9) | |
C33 | 1.2333 (4) | 0.4839 (4) | 0.0904 (2) | 0.0406 (11) | |
H33 | 1.3185 | 0.4810 | 0.0796 | 0.049* | |
C34 | 1.1706 (4) | 0.4024 (3) | 0.1293 (2) | 0.0358 (10) | |
H34 | 1.2130 | 0.3443 | 0.1443 | 0.043* | |
C35 | 1.2479 (4) | 0.6655 (3) | 0.0295 (2) | 0.0372 (10) | |
H35A | 1.3120 | 0.6333 | 0.0028 | 0.045* | |
H35B | 1.1876 | 0.6915 | −0.0035 | 0.045* | |
C36 | 1.3479 (4) | 0.8788 (3) | 0.06507 (19) | 0.0306 (9) | |
H36 | 1.3297 | 0.9020 | 0.0212 | 0.037* | |
C37 | 1.4127 (4) | 0.8816 (4) | 0.1728 (2) | 0.0439 (11) | |
H37 | 1.4488 | 0.9082 | 0.2187 | 0.053* | |
C38 | 1.3572 (4) | 0.7693 (4) | 0.1486 (2) | 0.0489 (12) | |
H38 | 1.3485 | 0.7047 | 0.1739 | 0.059* | |
C39 | −0.1608 (4) | 0.3296 (4) | 0.5787 (2) | 0.0410 (10) | |
H39 | −0.1389 | 0.3109 | 0.5332 | 0.049* | |
C40 | −0.1474 (4) | 0.3919 (4) | 0.6870 (2) | 0.0575 (14) | |
H40 | −0.1141 | 0.4245 | 0.7325 | 0.069* | |
C41 | −0.2746 (4) | 0.3482 (5) | 0.6666 (2) | 0.0666 (15) | |
H41 | −0.3442 | 0.3466 | 0.6947 | 0.080* | |
C42 | −0.4026 (4) | 0.2510 (4) | 0.5520 (2) | 0.0574 (13) | |
H42A | −0.3791 | 0.2161 | 0.5075 | 0.069* | |
H42B | −0.4530 | 0.3109 | 0.5423 | 0.069* | |
C43 | −0.4853 (4) | 0.1565 (4) | 0.5865 (2) | 0.0448 (11) | |
C44 | −0.4556 (4) | 0.0454 (4) | 0.5854 (2) | 0.0492 (12) | |
H44 | −0.3867 | 0.0266 | 0.5609 | 0.059* | |
C45 | −0.5281 (5) | −0.0383 (4) | 0.6207 (2) | 0.0503 (12) | |
H45 | −0.5071 | −0.1131 | 0.6198 | 0.060* | |
C46 | −0.6316 (4) | −0.0125 (4) | 0.6573 (2) | 0.0401 (10) | |
C47 | −0.6602 (4) | 0.0979 (4) | 0.6577 (2) | 0.0483 (12) | |
H47 | −0.7300 | 0.1162 | 0.6817 | 0.058* | |
C48 | −0.5889 (4) | 0.1820 (4) | 0.6238 (2) | 0.0461 (11) | |
H48 | −0.6097 | 0.2570 | 0.6256 | 0.055* | |
C49 | −0.7005 (5) | −0.0992 (4) | 0.7018 (2) | 0.0532 (12) | |
H49A | −0.6354 | −0.1214 | 0.7336 | 0.064* | |
H49B | −0.7574 | −0.0602 | 0.7302 | 0.064* | |
C50 | −0.7537 (4) | −0.3163 (4) | 0.6613 (2) | 0.0377 (10) | |
H50 | −0.6779 | −0.3332 | 0.6830 | 0.045* | |
C51 | −0.9397 (4) | −0.3331 (4) | 0.6034 (2) | 0.0433 (11) | |
H51 | −1.0188 | −0.3659 | 0.5770 | 0.052* | |
C52 | −0.8975 (4) | −0.2183 (4) | 0.6244 (2) | 0.0513 (12) | |
H52 | −0.9405 | −0.1570 | 0.6155 | 0.062* | |
N1 | 0.6596 (3) | 0.1573 (3) | 0.12458 (15) | 0.0268 (7) | |
N2 | 0.8624 (3) | 0.2393 (3) | 0.16229 (15) | 0.0303 (8) | |
N3 | 1.3158 (3) | 0.7682 (3) | 0.07956 (16) | 0.0308 (7) | |
N4 | 1.4084 (3) | 0.9518 (3) | 0.11971 (16) | 0.0305 (8) | |
N5 | −0.0744 (3) | 0.3814 (3) | 0.63125 (17) | 0.0373 (8) | |
N6 | −0.2822 (3) | 0.3068 (3) | 0.59723 (17) | 0.0424 (9) | |
N7 | −0.7797 (3) | −0.2080 (3) | 0.66147 (16) | 0.0379 (8) | |
N8 | −0.8493 (3) | −0.3961 (3) | 0.62635 (16) | 0.0333 (8) | |
O1 | 0.1452 (3) | 0.3404 (3) | 0.53991 (13) | 0.0447 (7) | |
O2 | 0.3522 (3) | 0.4298 (3) | 0.56122 (15) | 0.0543 (8) | |
O3 | 0.2339 (3) | 0.1529 (3) | 0.19147 (14) | 0.0507 (8) | |
O4 | 0.4494 (3) | 0.2037 (3) | 0.21793 (13) | 0.0457 (7) | |
O5 | 0.3688 (2) | 0.1459 (2) | 0.03180 (13) | 0.0363 (6) | |
O6 | 0.4696 (3) | 0.3310 (3) | 0.06274 (14) | 0.0459 (7) | |
O7 | 0.2240 (5) | 0.4703 (4) | −0.2604 (2) | 0.1041 (16) | |
O8 | 0.1547 (4) | 0.2877 (4) | −0.29806 (18) | 0.0896 (14) | |
Zn2 | 0.12582 (4) | 0.42540 (4) | 0.63090 (2) | 0.03215 (14) | |
Zn1 | 0.46017 (4) | 0.13060 (4) | 0.12193 (2) | 0.02786 (13) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.041 (3) | 0.037 (3) | 0.028 (2) | 0.012 (2) | −0.002 (2) | 0.0020 (19) |
C2 | 0.026 (2) | 0.038 (3) | 0.025 (2) | 0.0062 (19) | 0.0006 (17) | 0.0000 (19) |
C3 | 0.048 (3) | 0.033 (3) | 0.043 (3) | 0.006 (2) | 0.010 (2) | −0.001 (2) |
C4 | 0.046 (3) | 0.041 (3) | 0.038 (3) | 0.007 (2) | 0.014 (2) | 0.008 (2) |
C5 | 0.037 (2) | 0.039 (3) | 0.028 (2) | 0.012 (2) | 0.0073 (18) | 0.005 (2) |
C6 | 0.053 (3) | 0.029 (2) | 0.034 (2) | 0.014 (2) | 0.012 (2) | 0.0092 (19) |
C7 | 0.038 (2) | 0.034 (2) | 0.025 (2) | 0.005 (2) | 0.0127 (18) | 0.0042 (19) |
C8 | 0.057 (3) | 0.045 (3) | 0.039 (3) | 0.003 (2) | 0.008 (2) | 0.000 (2) |
C9 | 0.063 (3) | 0.039 (3) | 0.046 (3) | −0.008 (2) | 0.012 (2) | 0.000 (2) |
C10 | 0.050 (3) | 0.045 (3) | 0.046 (3) | 0.004 (2) | 0.019 (2) | 0.012 (2) |
C11 | 0.038 (2) | 0.042 (3) | 0.032 (2) | 0.006 (2) | 0.0105 (19) | 0.004 (2) |
C12 | 0.026 (2) | 0.035 (3) | 0.031 (2) | 0.0046 (19) | 0.0044 (17) | 0.0029 (19) |
C13 | 0.025 (2) | 0.043 (3) | 0.026 (2) | 0.011 (2) | 0.0037 (17) | 0.003 (2) |
C14 | 0.030 (2) | 0.028 (2) | 0.026 (2) | 0.0066 (18) | 0.0042 (17) | 0.0078 (17) |
C15 | 0.032 (2) | 0.040 (3) | 0.041 (3) | 0.003 (2) | 0.0014 (19) | 0.010 (2) |
C16 | 0.053 (3) | 0.044 (3) | 0.056 (3) | 0.017 (2) | 0.024 (2) | 0.027 (2) |
C17 | 0.048 (3) | 0.053 (3) | 0.029 (2) | 0.033 (2) | 0.009 (2) | 0.013 (2) |
C18 | 0.070 (4) | 0.099 (5) | 0.050 (3) | 0.057 (4) | 0.033 (3) | 0.032 (3) |
C19 | 0.037 (2) | 0.031 (2) | 0.025 (2) | 0.015 (2) | 0.0038 (18) | 0.0008 (18) |
C20 | 0.053 (3) | 0.055 (3) | 0.031 (2) | 0.026 (3) | −0.012 (2) | −0.004 (2) |
C21 | 0.040 (3) | 0.048 (3) | 0.055 (3) | 0.005 (2) | −0.006 (2) | −0.007 (2) |
C22 | 0.033 (2) | 0.029 (2) | 0.069 (3) | 0.002 (2) | 0.004 (2) | 0.008 (2) |
C23 | 0.037 (2) | 0.032 (2) | 0.037 (2) | 0.010 (2) | 0.0002 (19) | 0.0088 (19) |
C24 | 0.030 (2) | 0.023 (2) | 0.031 (2) | 0.0092 (18) | 0.0054 (17) | 0.0052 (17) |
C25 | 0.031 (2) | 0.027 (2) | 0.030 (2) | 0.0064 (19) | 0.0082 (17) | 0.0057 (18) |
C26 | 0.039 (2) | 0.026 (2) | 0.037 (2) | 0.008 (2) | 0.0082 (19) | 0.0001 (18) |
C27 | 0.034 (2) | 0.040 (3) | 0.042 (3) | 0.014 (2) | 0.0081 (19) | 0.006 (2) |
C28 | 0.035 (2) | 0.043 (3) | 0.036 (2) | −0.003 (2) | −0.0012 (19) | 0.004 (2) |
C29 | 0.031 (2) | 0.024 (2) | 0.034 (2) | −0.0051 (19) | −0.0032 (18) | −0.0052 (18) |
C30 | 0.025 (2) | 0.044 (3) | 0.039 (2) | 0.008 (2) | 0.0079 (19) | −0.002 (2) |
C31 | 0.033 (2) | 0.030 (2) | 0.040 (2) | 0.0061 (19) | −0.0008 (19) | 0.001 (2) |
C32 | 0.033 (2) | 0.024 (2) | 0.034 (2) | 0.0012 (19) | 0.0013 (18) | −0.0047 (18) |
C33 | 0.025 (2) | 0.035 (3) | 0.063 (3) | 0.004 (2) | 0.016 (2) | 0.007 (2) |
C34 | 0.028 (2) | 0.028 (2) | 0.049 (3) | 0.0015 (19) | 0.0008 (19) | 0.007 (2) |
C35 | 0.041 (2) | 0.032 (2) | 0.034 (2) | −0.002 (2) | 0.0041 (19) | 0.0014 (19) |
C36 | 0.037 (2) | 0.030 (2) | 0.023 (2) | −0.0001 (19) | 0.0021 (17) | 0.0044 (18) |
C37 | 0.060 (3) | 0.039 (3) | 0.026 (2) | −0.003 (2) | −0.012 (2) | 0.006 (2) |
C38 | 0.074 (3) | 0.035 (3) | 0.033 (3) | −0.002 (2) | −0.010 (2) | 0.014 (2) |
C39 | 0.047 (3) | 0.044 (3) | 0.030 (2) | 0.002 (2) | 0.009 (2) | 0.006 (2) |
C40 | 0.044 (3) | 0.071 (4) | 0.043 (3) | −0.014 (3) | 0.006 (2) | −0.019 (2) |
C41 | 0.044 (3) | 0.092 (4) | 0.051 (3) | −0.010 (3) | 0.017 (2) | −0.016 (3) |
C42 | 0.043 (3) | 0.073 (4) | 0.047 (3) | −0.013 (3) | −0.010 (2) | 0.023 (3) |
C43 | 0.039 (3) | 0.049 (3) | 0.040 (3) | −0.009 (2) | −0.014 (2) | 0.015 (2) |
C44 | 0.036 (3) | 0.058 (3) | 0.050 (3) | 0.006 (2) | 0.002 (2) | 0.000 (3) |
C45 | 0.061 (3) | 0.041 (3) | 0.048 (3) | 0.013 (3) | −0.006 (2) | 0.008 (2) |
C46 | 0.050 (3) | 0.037 (3) | 0.029 (2) | 0.002 (2) | −0.007 (2) | 0.004 (2) |
C47 | 0.044 (3) | 0.039 (3) | 0.060 (3) | 0.006 (2) | 0.000 (2) | 0.008 (2) |
C48 | 0.043 (3) | 0.037 (3) | 0.055 (3) | 0.002 (2) | −0.005 (2) | 0.012 (2) |
C49 | 0.072 (3) | 0.044 (3) | 0.034 (3) | −0.010 (3) | −0.004 (2) | 0.008 (2) |
C50 | 0.031 (2) | 0.045 (3) | 0.039 (2) | 0.009 (2) | −0.0007 (19) | 0.016 (2) |
C51 | 0.030 (2) | 0.050 (3) | 0.049 (3) | 0.005 (2) | −0.0093 (19) | 0.013 (2) |
C52 | 0.048 (3) | 0.048 (3) | 0.061 (3) | 0.013 (3) | −0.006 (2) | 0.021 (2) |
N1 | 0.0260 (17) | 0.0250 (19) | 0.0287 (17) | 0.0017 (16) | 0.0035 (14) | 0.0056 (15) |
N2 | 0.0292 (19) | 0.031 (2) | 0.0293 (18) | 0.0015 (16) | 0.0057 (14) | 0.0056 (15) |
N3 | 0.0324 (18) | 0.027 (2) | 0.0312 (19) | 0.0006 (15) | 0.0030 (14) | 0.0053 (15) |
N4 | 0.0291 (18) | 0.0274 (19) | 0.0330 (19) | 0.0000 (15) | 0.0001 (15) | 0.0060 (16) |
N5 | 0.0355 (19) | 0.038 (2) | 0.034 (2) | −0.0030 (17) | 0.0036 (16) | 0.0019 (16) |
N6 | 0.032 (2) | 0.049 (2) | 0.040 (2) | −0.0090 (17) | −0.0001 (16) | 0.0070 (18) |
N7 | 0.041 (2) | 0.036 (2) | 0.033 (2) | −0.0015 (17) | −0.0034 (16) | 0.0122 (16) |
N8 | 0.0280 (18) | 0.040 (2) | 0.0295 (18) | 0.0014 (17) | −0.0013 (15) | 0.0065 (16) |
O1 | 0.0410 (17) | 0.065 (2) | 0.0262 (15) | 0.0090 (16) | 0.0081 (13) | −0.0039 (14) |
O2 | 0.0513 (19) | 0.059 (2) | 0.0440 (18) | 0.0029 (17) | −0.0034 (15) | −0.0128 (16) |
O3 | 0.059 (2) | 0.060 (2) | 0.0321 (17) | 0.0118 (17) | 0.0008 (15) | 0.0033 (15) |
O4 | 0.0512 (19) | 0.057 (2) | 0.0329 (16) | 0.0155 (16) | 0.0173 (14) | 0.0052 (14) |
O5 | 0.0422 (16) | 0.0345 (18) | 0.0314 (15) | 0.0035 (14) | −0.0045 (12) | 0.0116 (13) |
O6 | 0.0459 (17) | 0.0438 (18) | 0.0438 (18) | 0.0069 (15) | −0.0142 (14) | 0.0014 (15) |
O7 | 0.166 (4) | 0.107 (4) | 0.073 (3) | 0.072 (3) | 0.043 (3) | 0.062 (3) |
O8 | 0.084 (3) | 0.164 (4) | 0.034 (2) | 0.058 (3) | 0.0053 (19) | 0.015 (2) |
Zn2 | 0.0352 (3) | 0.0368 (3) | 0.0231 (3) | 0.0039 (2) | 0.0028 (2) | 0.0030 (2) |
Zn1 | 0.0278 (2) | 0.0307 (3) | 0.0237 (3) | 0.0017 (2) | 0.00036 (19) | 0.0051 (2) |
C1—O2 | 1.223 (5) | C31—C32 | 1.380 (5) |
C1—O1 | 1.272 (4) | C31—H31 | 0.9300 |
C1—C2 | 1.513 (5) | C32—C33 | 1.371 (5) |
C2—C3 | 1.372 (5) | C32—C35 | 1.509 (5) |
C2—C12 | 1.421 (5) | C33—C34 | 1.368 (5) |
C3—C4 | 1.402 (5) | C33—H33 | 0.9300 |
C3—H3 | 0.9300 | C34—H34 | 0.9300 |
C4—C5 | 1.362 (5) | C35—N3 | 1.477 (5) |
C4—H4 | 0.9300 | C35—H35A | 0.9700 |
C5—C7 | 1.414 (5) | C35—H35B | 0.9700 |
C5—C6 | 1.516 (5) | C36—N4 | 1.316 (4) |
C6—O3 | 1.231 (5) | C36—N3 | 1.326 (5) |
C6—O4 | 1.277 (5) | C36—H36 | 0.9300 |
C7—C8 | 1.426 (5) | C37—C38 | 1.339 (6) |
C7—C12 | 1.431 (5) | C37—N4 | 1.375 (5) |
C8—C9 | 1.353 (6) | C37—H37 | 0.9300 |
C8—H8 | 0.9300 | C38—N3 | 1.363 (5) |
C9—C10 | 1.397 (6) | C38—H38 | 0.9300 |
C9—H9 | 0.9300 | C39—N5 | 1.316 (5) |
C10—C11 | 1.358 (5) | C39—N6 | 1.323 (5) |
C10—H10 | 0.9300 | C39—H39 | 0.9300 |
C11—C12 | 1.414 (5) | C40—C41 | 1.342 (6) |
C11—H11 | 0.9300 | C40—N5 | 1.361 (5) |
C13—O6 | 1.228 (4) | C40—H40 | 0.9300 |
C13—O5 | 1.275 (5) | C41—N6 | 1.356 (5) |
C13—C14 | 1.506 (5) | C41—H41 | 0.9300 |
C14—C15 | 1.358 (5) | C42—N6 | 1.474 (5) |
C14—C24 | 1.432 (5) | C42—C43 | 1.505 (6) |
C15—C16 | 1.415 (6) | C42—H42A | 0.9700 |
C15—H15 | 0.9300 | C42—H42B | 0.9700 |
C16—C17 | 1.354 (6) | C43—C44 | 1.376 (6) |
C16—H16 | 0.9300 | C43—C48 | 1.392 (6) |
C17—C19 | 1.445 (6) | C44—C45 | 1.382 (6) |
C17—C18 | 1.527 (6) | C44—H44 | 0.9300 |
C18—O8 | 1.220 (7) | C45—C46 | 1.386 (6) |
C18—O7 | 1.222 (6) | C45—H45 | 0.9300 |
C19—C24 | 1.409 (5) | C46—C47 | 1.363 (6) |
C19—C20 | 1.420 (6) | C46—C49 | 1.502 (6) |
C20—C21 | 1.365 (6) | C47—C48 | 1.364 (6) |
C20—H20 | 0.9300 | C47—H47 | 0.9300 |
C21—C22 | 1.394 (6) | C48—H48 | 0.9300 |
C21—H21 | 0.9300 | C49—N7 | 1.476 (5) |
C22—C23 | 1.356 (5) | C49—H49A | 0.9700 |
C22—H22 | 0.9300 | C49—H49B | 0.9700 |
C23—C24 | 1.412 (5) | C50—N8 | 1.315 (5) |
C23—H23 | 0.9300 | C50—N7 | 1.330 (5) |
C25—N1 | 1.313 (4) | C50—H50 | 0.9300 |
C25—N2 | 1.334 (4) | C51—C52 | 1.328 (6) |
C25—H25 | 0.9300 | C51—N8 | 1.371 (5) |
C26—C27 | 1.343 (5) | C51—H51 | 0.9300 |
C26—N1 | 1.377 (4) | C52—N7 | 1.354 (5) |
C26—H26 | 0.9300 | C52—H52 | 0.9300 |
C27—N2 | 1.367 (5) | Zn1—O4 | 1.960 (3) |
C27—H27 | 0.9300 | Zn1—O5 | 1.958 (2) |
C28—N2 | 1.472 (5) | Zn1—N1 | 2.038 (3) |
C28—C29 | 1.507 (5) | Zn1—N4i | 2.035 (3) |
C28—H28A | 0.9700 | Zn2—O1 | 1.950 (2) |
C28—H28B | 0.9700 | Zn2—O7ii | 2.224 (4) |
C29—C30 | 1.384 (5) | Zn2—O8ii | 2.256 (4) |
C29—C34 | 1.395 (5) | Zn2—N5 | 2.053 (3) |
C30—C31 | 1.363 (5) | Zn2—N8iii | 2.046 (3) |
C30—H30 | 0.9300 | ||
O2—C1—O1 | 123.8 (4) | C32—C35—H35A | 109.3 |
O2—C1—C2 | 120.3 (4) | N3—C35—H35B | 109.3 |
O1—C1—C2 | 115.9 (4) | C32—C35—H35B | 109.3 |
C3—C2—C12 | 119.6 (3) | H35A—C35—H35B | 108.0 |
C3—C2—C1 | 117.9 (4) | N4—C36—N3 | 112.5 (3) |
C12—C2—C1 | 122.4 (3) | N4—C36—H36 | 123.8 |
C2—C3—C4 | 121.0 (4) | N3—C36—H36 | 123.8 |
C2—C3—H3 | 119.5 | C38—C37—N4 | 109.9 (4) |
C4—C3—H3 | 119.5 | C38—C37—H37 | 125.1 |
C5—C4—C3 | 121.3 (4) | N4—C37—H37 | 125.1 |
C5—C4—H4 | 119.4 | C37—C38—N3 | 106.6 (4) |
C3—C4—H4 | 119.4 | C37—C38—H38 | 126.7 |
C4—C5—C7 | 119.3 (4) | N3—C38—H38 | 126.7 |
C4—C5—C6 | 119.5 (4) | N5—C39—N6 | 113.1 (3) |
C7—C5—C6 | 121.1 (4) | N5—C39—H39 | 123.5 |
O3—C6—O4 | 124.5 (4) | N6—C39—H39 | 123.5 |
O3—C6—C5 | 120.5 (4) | C41—C40—N5 | 110.0 (4) |
O4—C6—C5 | 115.0 (4) | C41—C40—H40 | 125.0 |
C5—C7—C8 | 122.4 (4) | N5—C40—H40 | 125.0 |
C5—C7—C12 | 120.1 (4) | C40—C41—N6 | 106.8 (4) |
C8—C7—C12 | 117.5 (3) | C40—C41—H41 | 126.6 |
C9—C8—C7 | 122.3 (4) | N6—C41—H41 | 126.6 |
C9—C8—H8 | 118.9 | N6—C42—C43 | 111.2 (3) |
C7—C8—H8 | 118.9 | N6—C42—H42A | 109.4 |
C8—C9—C10 | 119.6 (4) | C43—C42—H42A | 109.4 |
C8—C9—H9 | 120.2 | N6—C42—H42B | 109.4 |
C10—C9—H9 | 120.2 | C43—C42—H42B | 109.4 |
C11—C10—C9 | 120.6 (4) | H42A—C42—H42B | 108.0 |
C11—C10—H10 | 119.7 | C44—C43—C48 | 118.6 (4) |
C9—C10—H10 | 119.7 | C44—C43—C42 | 120.8 (4) |
C10—C11—C12 | 121.7 (4) | C48—C43—C42 | 120.6 (4) |
C10—C11—H11 | 119.2 | C43—C44—C45 | 120.1 (4) |
C12—C11—H11 | 119.2 | C43—C44—H44 | 120.0 |
C11—C12—C2 | 123.4 (4) | C45—C44—H44 | 120.0 |
C11—C12—C7 | 118.1 (4) | C44—C45—C46 | 121.0 (4) |
C2—C12—C7 | 118.4 (3) | C44—C45—H45 | 119.5 |
O6—C13—O5 | 123.3 (4) | C46—C45—H45 | 119.5 |
O6—C13—C14 | 119.9 (4) | C47—C46—C45 | 118.3 (4) |
O5—C13—C14 | 116.7 (3) | C47—C46—C49 | 120.8 (4) |
C15—C14—C24 | 119.1 (3) | C45—C46—C49 | 120.5 (4) |
C15—C14—C13 | 117.8 (3) | C46—C47—C48 | 121.6 (4) |
C24—C14—C13 | 123.0 (3) | C46—C47—H47 | 119.2 |
C14—C15—C16 | 121.2 (4) | C48—C47—H47 | 119.2 |
C14—C15—H15 | 119.4 | C47—C48—C43 | 120.5 (4) |
C16—C15—H15 | 119.4 | C47—C48—H48 | 119.7 |
C17—C16—C15 | 121.2 (4) | C43—C48—H48 | 119.7 |
C17—C16—H16 | 119.4 | N7—C49—C46 | 114.5 (3) |
C15—C16—H16 | 119.4 | N7—C49—H49A | 108.6 |
C16—C17—C19 | 119.4 (4) | C46—C49—H49A | 108.6 |
C16—C17—C18 | 118.6 (5) | N7—C49—H49B | 108.6 |
C19—C17—C18 | 122.0 (4) | C46—C49—H49B | 108.6 |
O8—C18—O7 | 121.5 (5) | H49A—C49—H49B | 107.6 |
O8—C18—C17 | 120.8 (6) | N8—C50—N7 | 110.9 (3) |
O7—C18—C17 | 117.8 (6) | N8—C50—H50 | 124.5 |
C24—C19—C20 | 119.1 (4) | N7—C50—H50 | 124.5 |
C24—C19—C17 | 118.9 (4) | C52—C51—N8 | 110.0 (4) |
C20—C19—C17 | 121.9 (4) | C52—C51—H51 | 125.0 |
C21—C20—C19 | 120.8 (4) | N8—C51—H51 | 125.0 |
C21—C20—H20 | 119.6 | C51—C52—N7 | 106.4 (4) |
C19—C20—H20 | 119.6 | C51—C52—H52 | 126.8 |
C20—C21—C22 | 119.7 (4) | N7—C52—H52 | 126.8 |
C20—C21—H21 | 120.1 | C25—N1—C26 | 105.6 (3) |
C22—C21—H21 | 120.1 | C25—N1—Zn1 | 123.8 (2) |
C23—C22—C21 | 120.7 (4) | C26—N1—Zn1 | 129.1 (2) |
C23—C22—H22 | 119.6 | C25—N2—C27 | 107.0 (3) |
C21—C22—H22 | 119.6 | C25—N2—C28 | 127.6 (3) |
C22—C23—C24 | 121.4 (4) | C27—N2—C28 | 125.3 (3) |
C22—C23—H23 | 119.3 | C36—N3—C38 | 106.7 (3) |
C24—C23—H23 | 119.3 | C36—N3—C35 | 125.6 (3) |
C19—C24—C23 | 118.0 (3) | C38—N3—C35 | 127.7 (3) |
C19—C24—C14 | 119.7 (3) | C36—N4—C37 | 104.4 (3) |
C23—C24—C14 | 122.1 (3) | C36—N4—Zn1iii | 124.8 (3) |
N1—C25—N2 | 111.5 (3) | C37—N4—Zn1iii | 130.5 (3) |
N1—C25—H25 | 124.2 | C39—N5—C40 | 104.0 (3) |
N2—C25—H25 | 124.2 | C39—N5—Zn2 | 127.9 (3) |
C27—C26—N1 | 109.2 (3) | C40—N5—Zn2 | 127.9 (3) |
C27—C26—H26 | 125.4 | C39—N6—C41 | 106.0 (3) |
N1—C26—H26 | 125.4 | C39—N6—C42 | 127.6 (4) |
C26—C27—N2 | 106.7 (3) | C41—N6—C42 | 126.4 (4) |
C26—C27—H27 | 126.7 | C50—N7—C52 | 107.6 (4) |
N2—C27—H27 | 126.7 | C50—N7—C49 | 125.3 (4) |
N2—C28—C29 | 113.7 (3) | C52—N7—C49 | 126.7 (4) |
N2—C28—H28A | 108.8 | C50—N8—C51 | 105.1 (3) |
C29—C28—H28A | 108.8 | C50—N8—Zn2i | 124.8 (3) |
N2—C28—H28B | 108.8 | C51—N8—Zn2i | 128.2 (3) |
C29—C28—H28B | 108.8 | C1—O1—Zn2 | 111.4 (2) |
H28A—C28—H28B | 107.7 | C6—O4—Zn1 | 111.6 (3) |
C30—C29—C34 | 117.6 (4) | C13—O5—Zn1 | 107.7 (2) |
C30—C29—C28 | 121.2 (3) | C18—O7—Zn2iv | 91.5 (4) |
C34—C29—C28 | 121.2 (4) | C18—O8—Zn2iv | 90.1 (4) |
C31—C30—C29 | 121.6 (4) | O5—Zn1—O4 | 131.58 (11) |
C31—C30—H30 | 119.2 | O5—Zn1—N4i | 98.42 (12) |
C29—C30—H30 | 119.2 | O4—Zn1—N4i | 108.08 (12) |
C30—C31—C32 | 120.4 (4) | O5—Zn1—N1 | 115.50 (11) |
C30—C31—H31 | 119.8 | O4—Zn1—N1 | 97.48 (12) |
C32—C31—H31 | 119.8 | N4i—Zn1—N1 | 102.78 (12) |
C33—C32—C31 | 118.7 (4) | O1—Zn2—N8iii | 111.14 (12) |
C33—C32—C35 | 120.4 (3) | O1—Zn2—N5 | 99.11 (12) |
C31—C32—C35 | 120.8 (4) | N8iii—Zn2—N5 | 100.87 (13) |
C34—C33—C32 | 121.3 (4) | O1—Zn2—O7ii | 140.89 (14) |
C34—C33—H33 | 119.4 | N8iii—Zn2—O7ii | 86.96 (15) |
C32—C33—H33 | 119.4 | N5—Zn2—O7ii | 111.53 (15) |
C33—C34—C29 | 120.4 (4) | O1—Zn2—O8ii | 100.20 (14) |
C33—C34—H34 | 119.8 | N8iii—Zn2—O8ii | 143.68 (15) |
C29—C34—H34 | 119.8 | N5—Zn2—O8ii | 91.51 (14) |
N3—C35—C32 | 111.6 (3) | O7ii—Zn2—O8ii | 56.80 (15) |
N3—C35—H35A | 109.3 | ||
O2—C1—C2—C3 | −41.9 (5) | C43—C44—C45—C46 | 0.3 (7) |
O1—C1—C2—C3 | 136.7 (4) | C44—C45—C46—C47 | −0.1 (6) |
O2—C1—C2—C12 | 141.6 (4) | C44—C45—C46—C49 | −173.4 (4) |
O1—C1—C2—C12 | −39.8 (5) | C45—C46—C47—C48 | −0.6 (6) |
C12—C2—C3—C4 | 3.5 (6) | C49—C46—C47—C48 | 172.7 (4) |
C1—C2—C3—C4 | −173.1 (4) | C46—C47—C48—C43 | 1.1 (7) |
C2—C3—C4—C5 | 2.4 (6) | C44—C43—C48—C47 | −0.8 (6) |
C3—C4—C5—C7 | −5.4 (6) | C42—C43—C48—C47 | −177.1 (4) |
C3—C4—C5—C6 | 178.1 (4) | C47—C46—C49—N7 | 117.3 (4) |
C4—C5—C6—O3 | −129.8 (4) | C45—C46—C49—N7 | −69.5 (5) |
C7—C5—C6—O3 | 53.8 (5) | N8—C51—C52—N7 | −0.4 (5) |
C4—C5—C6—O4 | 50.0 (5) | N2—C25—N1—C26 | −0.2 (4) |
C7—C5—C6—O4 | −126.5 (4) | N2—C25—N1—Zn1 | 167.0 (2) |
C4—C5—C7—C8 | −175.2 (4) | C27—C26—N1—C25 | 0.0 (4) |
C6—C5—C7—C8 | 1.3 (6) | C27—C26—N1—Zn1 | −166.2 (3) |
C4—C5—C7—C12 | 2.5 (6) | N1—C25—N2—C27 | 0.3 (4) |
C6—C5—C7—C12 | 179.0 (3) | N1—C25—N2—C28 | −177.9 (3) |
C5—C7—C8—C9 | 174.8 (4) | C26—C27—N2—C25 | −0.3 (4) |
C12—C7—C8—C9 | −3.0 (6) | C26—C27—N2—C28 | 178.0 (3) |
C7—C8—C9—C10 | −1.1 (7) | C29—C28—N2—C25 | −88.0 (5) |
C8—C9—C10—C11 | 3.9 (7) | C29—C28—N2—C27 | 94.2 (4) |
C9—C10—C11—C12 | −2.5 (6) | N4—C36—N3—C38 | 0.5 (4) |
C10—C11—C12—C2 | −178.3 (4) | N4—C36—N3—C35 | −179.6 (3) |
C10—C11—C12—C7 | −1.7 (6) | C37—C38—N3—C36 | 0.1 (5) |
C3—C2—C12—C11 | 170.5 (4) | C37—C38—N3—C35 | −179.8 (3) |
C1—C2—C12—C11 | −13.2 (6) | C32—C35—N3—C36 | −154.0 (3) |
C3—C2—C12—C7 | −6.1 (5) | C32—C35—N3—C38 | 25.8 (5) |
C1—C2—C12—C7 | 170.3 (3) | N3—C36—N4—C37 | −0.9 (4) |
C5—C7—C12—C11 | −173.6 (4) | N3—C36—N4—Zn1iii | −174.6 (2) |
C8—C7—C12—C11 | 4.2 (5) | C38—C37—N4—C36 | 0.9 (5) |
C5—C7—C12—C2 | 3.2 (5) | C38—C37—N4—Zn1iii | 174.2 (3) |
C8—C7—C12—C2 | −179.0 (3) | N6—C39—N5—C40 | 0.0 (5) |
O6—C13—C14—C15 | 33.3 (5) | N6—C39—N5—Zn2 | 176.0 (3) |
O5—C13—C14—C15 | −143.4 (3) | C41—C40—N5—C39 | −0.9 (5) |
O6—C13—C14—C24 | −148.8 (3) | C41—C40—N5—Zn2 | −176.9 (3) |
O5—C13—C14—C24 | 34.5 (5) | N5—C39—N6—C41 | 0.9 (5) |
C24—C14—C15—C16 | −5.2 (6) | N5—C39—N6—C42 | 179.4 (4) |
C13—C14—C15—C16 | 172.7 (3) | C40—C41—N6—C39 | −1.4 (6) |
C14—C15—C16—C17 | −1.8 (6) | C40—C41—N6—C42 | −179.9 (4) |
C15—C16—C17—C19 | 5.6 (6) | C43—C42—N6—C39 | 133.6 (5) |
C15—C16—C17—C18 | −178.2 (4) | C43—C42—N6—C41 | −48.2 (7) |
C16—C17—C18—O8 | 140.4 (5) | N8—C50—N7—C52 | −0.4 (4) |
C19—C17—C18—O8 | −43.5 (6) | N8—C50—N7—C49 | 173.3 (3) |
C16—C17—C18—O7 | −39.4 (6) | C51—C52—N7—C50 | 0.5 (5) |
C19—C17—C18—O7 | 136.7 (5) | C51—C52—N7—C49 | −173.1 (4) |
C16—C17—C19—C24 | −2.3 (5) | C46—C49—N7—C50 | 112.5 (4) |
C18—C17—C19—C24 | −178.3 (4) | C46—C49—N7—C52 | −74.9 (6) |
C16—C17—C19—C20 | 173.2 (4) | N7—C50—N8—C51 | 0.1 (4) |
C18—C17—C19—C20 | −2.8 (6) | N7—C50—N8—Zn2i | −165.0 (2) |
C24—C19—C20—C21 | 3.7 (6) | C52—C51—N8—C50 | 0.2 (5) |
C17—C19—C20—C21 | −171.8 (4) | C52—C51—N8—Zn2i | 164.6 (3) |
C19—C20—C21—C22 | 0.3 (6) | O2—C1—O1—Zn2 | 2.5 (5) |
C20—C21—C22—C23 | −2.6 (6) | C2—C1—O1—Zn2 | −176.0 (2) |
C21—C22—C23—C24 | 1.0 (6) | O3—C6—O4—Zn1 | −8.4 (5) |
C20—C19—C24—C23 | −5.2 (5) | C5—C6—O4—Zn1 | 171.9 (2) |
C17—C19—C24—C23 | 170.5 (3) | O6—C13—O5—Zn1 | 3.8 (4) |
C20—C19—C24—C14 | 179.7 (3) | C14—C13—O5—Zn1 | −179.6 (2) |
C17—C19—C24—C14 | −4.6 (5) | O8—C18—O7—Zn2iv | 4.1 (5) |
C22—C23—C24—C19 | 2.9 (5) | C17—C18—O7—Zn2iv | −176.0 (3) |
C22—C23—C24—C14 | 177.9 (3) | O7—C18—O8—Zn2iv | −4.1 (5) |
C15—C14—C24—C19 | 8.4 (5) | C17—C18—O8—Zn2iv | 176.1 (4) |
C13—C14—C24—C19 | −169.4 (3) | C1—O1—Zn2—N8iii | 67.2 (3) |
C15—C14—C24—C23 | −166.5 (3) | C1—O1—Zn2—N5 | 172.7 (3) |
C13—C14—C24—C23 | 15.6 (5) | C1—O1—Zn2—O7ii | −45.5 (4) |
N1—C26—C27—N2 | 0.1 (4) | C1—O1—Zn2—O8ii | −94.1 (3) |
N2—C28—C29—C30 | 68.1 (5) | C39—N5—Zn2—O1 | −10.9 (4) |
N2—C28—C29—C34 | −115.1 (4) | C40—N5—Zn2—O1 | 164.2 (4) |
C34—C29—C30—C31 | −3.0 (6) | C39—N5—Zn2—N8iii | 102.9 (4) |
C28—C29—C30—C31 | 173.8 (4) | C40—N5—Zn2—N8iii | −82.0 (4) |
C29—C30—C31—C32 | −0.1 (6) | C39—N5—Zn2—O7ii | −166.1 (3) |
C30—C31—C32—C33 | 2.9 (6) | C40—N5—Zn2—O7ii | 9.0 (4) |
C30—C31—C32—C35 | −174.1 (4) | C39—N5—Zn2—O8ii | −111.5 (4) |
C31—C32—C33—C34 | −2.5 (6) | C40—N5—Zn2—O8ii | 63.7 (4) |
C35—C32—C33—C34 | 174.6 (4) | C13—O5—Zn1—O4 | 58.9 (3) |
C32—C33—C34—C29 | −0.7 (6) | C13—O5—Zn1—N4i | −177.7 (2) |
C30—C29—C34—C33 | 3.4 (6) | C13—O5—Zn1—N1 | −69.1 (2) |
C28—C29—C34—C33 | −173.4 (4) | C6—O4—Zn1—O5 | 50.7 (3) |
C33—C32—C35—N3 | −88.3 (4) | C6—O4—Zn1—N4i | −69.0 (3) |
C31—C32—C35—N3 | 88.7 (4) | C6—O4—Zn1—N1 | −175.1 (3) |
N4—C37—C38—N3 | −0.6 (5) | C25—N1—Zn1—O5 | 104.5 (3) |
N5—C40—C41—N6 | 1.4 (6) | C26—N1—Zn1—O5 | −91.5 (3) |
N6—C42—C43—C44 | −80.0 (5) | C25—N1—Zn1—O4 | −39.1 (3) |
N6—C42—C43—C48 | 96.2 (5) | C26—N1—Zn1—O4 | 124.9 (3) |
C48—C43—C44—C45 | 0.1 (6) | C25—N1—Zn1—N4i | −149.6 (3) |
C42—C43—C44—C45 | 176.4 (4) | C26—N1—Zn1—N4i | 14.4 (3) |
Symmetry codes: (i) x−1, y−1, z; (ii) x, y, z+1; (iii) x+1, y+1, z; (iv) x, y, z−1. |
Experimental details
Crystal data | |
Chemical formula | [Zn(C12H6O4)(C14H14N4)] |
Mr | 517.83 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 10.4112 (5), 11.5745 (5), 19.1907 (9) |
α, β, γ (°) | 96.319 (4), 93.869 (5), 100.628 (4) |
V (Å3) | 2249.95 (18) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.13 |
Crystal size (mm) | 0.33 × 0.27 × 0.22 |
Data collection | |
Diffractometer | Bruker APEX diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.680, 0.775 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 22060, 9159, 4749 |
Rint | 0.051 |
(sin θ/λ)max (Å−1) | 0.625 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.046, 0.096, 0.83 |
No. of reflections | 9159 |
No. of parameters | 631 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.74, −0.44 |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL-Plus (Sheldrick, 2008), publCIF (Westrip, 2009).
Zn1—O4 | 1.960 (3) | Zn2—O7ii | 2.224 (4) |
Zn1—O5 | 1.958 (2) | Zn2—O8ii | 2.256 (4) |
Zn1—N1 | 2.038 (3) | Zn2—N5 | 2.053 (3) |
Zn1—N4i | 2.035 (3) | Zn2—N8iii | 2.046 (3) |
O5—Zn1—O4 | 131.58 (11) | N8iii—Zn2—N5 | 100.87 (13) |
O5—Zn1—N4i | 98.42 (12) | O1—Zn2—O7ii | 140.89 (14) |
O4—Zn1—N4i | 108.08 (12) | N8iii—Zn2—O7ii | 86.96 (15) |
O5—Zn1—N1 | 115.50 (11) | N5—Zn2—O7ii | 111.53 (15) |
O4—Zn1—N1 | 97.48 (12) | O1—Zn2—O8ii | 100.20 (14) |
N4i—Zn1—N1 | 102.78 (12) | N8iii—Zn2—O8ii | 143.68 (15) |
O1—Zn2—N8iii | 111.14 (12) | N5—Zn2—O8ii | 91.51 (14) |
O1—Zn2—N5 | 99.11 (12) | O7ii—Zn2—O8ii | 56.80 (15) |
Symmetry codes: (i) x−1, y−1, z; (ii) x, y, z+1; (iii) x+1, y+1, z. |
The current interest in polymeric coordination networks is rapidly expanding not only for their potential applications in medical chemistry, host–guest chemistry, ion exchange, gas storage and nonlinear optics, but also for their intriguing variety of topologies (Carlucci et al., 2003; Eddaoudi et al., 2001). It is well known that structural diversity in coordination polymers can occur as a result of various processes, including supramolecular isomerism and interpenetration. In this regard, interpenetrating networks, as an important subject in the area of entanglement, have provided a long-standing fascination for chemists (Batten & Robson, 1998; Ockwig et al., 2005). Generally, the topology of a coordination polymer can often be controlled and modified by selecting the coordination geometry preferred by the metal ion and the chemical structure of the organic ligand chosen (Batten, 2001). Flexible N-donor ligands are good candidates for the assembly of versatile entangled structures, owing to their propensity to form large voids, of which bis(imidazole) ligands are a good choice. Using these ligands, many intriguing varieties of interpenetrating architectures and topologies have been constructed (Sun et al., 2009). Among the bis(imidazole) ligands, 1,4-bis(imidazol-1-ylmethyl)benzene (1,4-bix) is particularly interesting. For example, the flexible bridging 1,4-bix gives an unusual infinite two-dimensional polyrotaxane network when it is reacted with CdII sulfate hexahydrate (Carlucci et al., 2005). An unusual triply interpenetrating α-polonium topology is produced when it is reacted with CdII nitrate hexahydrate (Abrahams et al., 2002). In the present study, 1,4-bis(imidazol-1-ylmethyl)benzene (1,4-bix) assembles with zinc naphthalene-1,4-dicarboxylate (1,4-ndc) to furnish a 1:1 adduct, [Zn(1,4-bix)(1,4-ndc)]2n (I), which exists as a twofold interpenetrating (4,4) topology.
The asymmetric unit of (I) (Fig. 1 and Table 1) contains two crystallographically independent ZnII atoms, two unique 1,4-ndc anions and two unique 1,4-bix ligands. The two ZnII atoms show different coordination spheres. Atom Zn1 is four-coordinated in a distorted tetrahedral environment surrounded by two carboxylate O atoms from two different 1,4-ndc anions and two N atoms from two distinct 1,4-bix ligands. The coordination of atom Zn2 is completed by two N atoms from two different 1,4-bix ligands, and three carboxylate O atoms from two different 1,4-ndc ligands in a distorted square-pyramidal enironment. One N atom (N5) and three O atoms (O1, O7ii and O8ii) constitute the base of the square-pyramid, whereas one N atom (N8iii) occupies the apical position with a Zn—N8iii distance of 2.046 (3) Å. The average Zn—O and Zn—N distances in (I) (Table 1) are comparable to those observed for [Zn(TITMB)(OAc)](OH).8.5H2O [TITMB is 1,3,5-tris(imidazol-1-ylmethyl)-2,4,6-trimethylbenzene and OAc is the acetate anion; Fan et al., 2003]. As depicted in Fig. 2, each ZnII center is bridged by the 1,4-ndc dianions and 1,4-bix ligands to give a two-dimensional four-connected (4,4) network. Along the c axis, the adjacent ZnII centers are linked via the two carboxylate groups of the 1,4-ndc ligands to form one-dimensional chains. The 1,4-bix ligands further extend these chains along the b axis, yielding the final two-dimensional (4,4) network. Interestingly, the two (4,4) networks are interpenetrated in a parallel mode in the (110) plane (Fig. 3). The two interpenetrating networks are individually generated by translation and they are related by inversion.
It is noteworthy that the structure of (I) is entirely different from those of the two related structures [Cu(1,3-bdc)2(1,4-bix)][Cu(1,4-bix)2(H2O)2].4H2O (1,3-bdc is 1,3-benzenedicarboxylate) and [Cu(1,4-ndc)(1,2-bix)2].2H2O (Yang et al., 2008). The reported complex [Cu(1,3-bdc)2(1,4-bix)][Cu(1,4-bix)2(H2O)2].4H2O consists of two types of coordination polymers, namely two-dimensional (4,4) grids of [Cu(1,4-bix)2(H2O)2]2+, and linear chains of [Cu(1,3-bdc)2(1,4-bix)]2-. The reported structure [Cu(1,4-ndc)(1,2-bix)2].2H2O contains two-dimensional (4,4) networks. However, this structure does not exhibit interpenetration. The structure of (I) is also entirely different from that of the related polymer [Zn(bis)1.5(H2O)(SO4)].6H2O [bis is 1,1'-(1,4-butanediyl)bis(imidazole); Ma et al., 2000]. In that structure, the networks are interpenetrated in an inclined mode by symmetry-related, identical networks to give an interlocked three-dimensional structure.