Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803010602/ww6086sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803010602/ww6086Isup2.hkl |
CCDC reference: 214789
EDTB (0.116 g, 0.2 mmol) was dissolved together with 0.059 g (0.2 mmol) of Zn(NO3)2·6H2O in 10 ml of ethanol. Colorless crystals were obtained from the solution after standing overnight at room temperature. The crystals were separated by filtration and dried in air (0.094 g, 58%). Analysis calculated for [Zn(EDTB)](NO3)2·C2H5OH: C 52.98, H 4.69, N 20.59%; Found: C 52.23, H 4.92, N 20.10%. IR (cm−1): 3109 (s), 2970 (s), 2918 (s), 1624 (m), 1595 (w), 1535 (m), 1470 (s), 1453 (s), 1383 (s), 1273 (s), 1120 (w), 1093 (m), 1038 (s), 989 (w), 939 (w), 826 (w), 741 (s), 504 (w), 430 (w).
All H atoms on C atoms were generated geometrically and refined as riding atoms, with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C). The H atom of the hydroxyl group was located from difference Fourier map and refined with Uiso(H) = 1.5Ueq(O).
Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1990).
Fig. 1. View of the local coordination of Zn(II) with the atomic numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. | |
Fig. 2. Packing diagram of (I) |
[Zn(C34H32N10)](NO3)2·C2H6O | Z = 2 |
Mr = 816.15 | F(000) = 848 |
Triclinic, P1 | Dx = 1.474 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 11.783 (3) Å | Cell parameters from 33 reflections |
b = 12.219 (4) Å | θ = 5.3–10.4° |
c = 14.468 (6) Å | µ = 0.74 mm−1 |
α = 91.42 (3)° | T = 293 K |
β = 103.51 (3)° | Block, colorless |
γ = 113.653 (18)° | 0.50 × 0.36 × 0.36 mm |
V = 1838.9 (11) Å3 |
Siemens P4 diffractometer | 3961 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.022 |
Graphite monochromator | θmax = 25.0°, θmin = 1.8° |
ω scans | h = −1→13 |
Absorption correction: empirical (using intensity measurements) via ψ scan (North et al., 1968) | k = −14→13 |
Tmin = 0.735, Tmax = 0.768 | l = −17→16 |
7751 measured reflections | 3 standard reflections every 97 reflections |
6479 independent reflections | intensity decay: none |
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)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.089 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.85 | w = 1/[σ2(Fo2) + (0.0349P)2] where P = (Fo2 + 2Fc2)/3 |
6479 reflections | (Δ/σ)max = 0.001 |
509 parameters | Δρmax = 0.26 e Å−3 |
2 restraints | Δρmin = −0.30 e Å−3 |
[Zn(C34H32N10)](NO3)2·C2H6O | γ = 113.653 (18)° |
Mr = 816.15 | V = 1838.9 (11) Å3 |
Triclinic, P1 | Z = 2 |
a = 11.783 (3) Å | Mo Kα radiation |
b = 12.219 (4) Å | µ = 0.74 mm−1 |
c = 14.468 (6) Å | T = 293 K |
α = 91.42 (3)° | 0.50 × 0.36 × 0.36 mm |
β = 103.51 (3)° |
Siemens P4 diffractometer | 3961 reflections with I > 2σ(I) |
Absorption correction: empirical (using intensity measurements) via ψ scan (North et al., 1968) | Rint = 0.022 |
Tmin = 0.735, Tmax = 0.768 | 3 standard reflections every 97 reflections |
7751 measured reflections | intensity decay: none |
6479 independent reflections |
R[F2 > 2σ(F2)] = 0.042 | 2 restraints |
wR(F2) = 0.089 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.85 | Δρmax = 0.26 e Å−3 |
6479 reflections | Δρmin = −0.30 e Å−3 |
509 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 | ||
Zn | 0.62262 (4) | 0.81089 (4) | 0.72370 (3) | 0.04054 (13) | |
N1 | 0.4715 (3) | 0.7750 (2) | 0.57566 (18) | 0.0429 (7) | |
N2 | 0.4776 (2) | 0.8363 (2) | 0.76022 (18) | 0.0396 (7) | |
N3 | 0.3193 (3) | 0.8921 (2) | 0.71996 (19) | 0.0502 (8) | |
H3 | 0.2633 | 0.9128 | 0.6849 | 0.050* | |
N4 | 0.5076 (3) | 0.6170 (2) | 0.70559 (19) | 0.0447 (7) | |
N5 | 0.3147 (3) | 0.4698 (2) | 0.6474 (2) | 0.0509 (8) | |
H5 | 0.2397 | 0.4293 | 0.6091 | 0.051* | |
N6 | 0.7335 (3) | 0.7936 (2) | 0.62202 (18) | 0.0443 (7) | |
N7 | 0.7814 (2) | 0.8038 (2) | 0.81595 (19) | 0.0420 (7) | |
N8 | 0.9218 (3) | 0.7230 (3) | 0.8318 (2) | 0.0538 (8) | |
H8 | 0.9658 | 0.6872 | 0.8164 | 0.054* | |
N9 | 0.7148 (2) | 0.9955 (2) | 0.69763 (18) | 0.0418 (7) | |
N10 | 0.8538 (3) | 1.1259 (3) | 0.62927 (19) | 0.0489 (7) | |
H10 | 0.9113 | 1.1534 | 0.5983 | 0.049* | |
N11 | 0.1498 (3) | 0.0462 (3) | 0.6324 (2) | 0.0640 (9) | |
N12 | 0.0151 (4) | 0.3603 (3) | 0.4818 (3) | 0.0628 (9) | |
O1 | 0.2134 (3) | 0.0127 (3) | 0.5903 (2) | 0.1001 (11) | |
O2 | 0.1349 (3) | 0.0107 (3) | 0.7092 (2) | 0.0984 (11) | |
O3 | 0.1032 (3) | 0.1141 (3) | 0.5965 (2) | 0.0852 (9) | |
O4 | −0.0973 (3) | 0.3112 (3) | 0.4333 (2) | 0.1096 (12) | |
O5 | 0.0443 (3) | 0.3317 (3) | 0.5619 (2) | 0.0896 (10) | |
O6 | 0.1000 (3) | 0.4364 (3) | 0.4520 (2) | 0.0861 (9) | |
O7 | 0.0516 (3) | 0.6129 (3) | 0.7580 (2) | 0.0861 (9) | |
H7A | 0.036 (5) | 0.618 (5) | 0.6984 (16) | 0.129* | |
C1 | 0.5474 (3) | 0.7990 (3) | 0.5047 (2) | 0.0511 (9) | |
H1A | 0.5931 | 0.8854 | 0.5062 | 0.051* | |
H1B | 0.4904 | 0.7659 | 0.4410 | 0.051* | |
C2 | 0.4172 (3) | 0.8612 (3) | 0.5902 (2) | 0.0476 (9) | |
H2A | 0.3341 | 0.8374 | 0.5444 | 0.048* | |
H2B | 0.4736 | 0.9410 | 0.5807 | 0.048* | |
C3 | 0.4029 (3) | 0.8627 (3) | 0.6901 (2) | 0.0404 (8) | |
C4 | 0.4365 (3) | 0.8471 (3) | 0.8419 (2) | 0.0387 (8) | |
C5 | 0.4772 (3) | 0.8227 (3) | 0.9332 (2) | 0.0459 (9) | |
H5A | 0.5420 | 0.7960 | 0.9492 | 0.046* | |
C6 | 0.4169 (3) | 0.8400 (3) | 0.9994 (3) | 0.0546 (10) | |
H6 | 0.4417 | 0.8249 | 1.0619 | 0.055* | |
C7 | 0.3193 (3) | 0.8797 (3) | 0.9748 (3) | 0.0561 (10) | |
H7 | 0.2818 | 0.8915 | 1.0218 | 0.056* | |
C8 | 0.2773 (3) | 0.9018 (3) | 0.8844 (3) | 0.0575 (10) | |
H8A | 0.2117 | 0.9276 | 0.8685 | 0.058* | |
C9 | 0.3375 (3) | 0.8839 (3) | 0.8168 (2) | 0.0420 (8) | |
C10 | 0.3733 (3) | 0.6490 (3) | 0.5592 (2) | 0.0506 (9) | |
H10A | 0.3696 | 0.6099 | 0.4987 | 0.051* | |
H10B | 0.2899 | 0.6491 | 0.5545 | 0.051* | |
C11 | 0.4005 (3) | 0.5784 (3) | 0.6372 (2) | 0.0435 (8) | |
C12 | 0.4904 (3) | 0.5279 (3) | 0.7665 (2) | 0.0434 (8) | |
C13 | 0.5679 (3) | 0.5220 (3) | 0.8523 (2) | 0.0522 (9) | |
H13 | 0.6498 | 0.5829 | 0.8779 | 0.052* | |
C14 | 0.5205 (4) | 0.4238 (3) | 0.8984 (3) | 0.0580 (10) | |
H14 | 0.5717 | 0.4186 | 0.9562 | 0.058* | |
C15 | 0.3994 (4) | 0.3323 (4) | 0.8622 (3) | 0.0700 (12) | |
H15 | 0.3707 | 0.2676 | 0.8962 | 0.070* | |
C16 | 0.3208 (4) | 0.3352 (3) | 0.7771 (3) | 0.0662 (11) | |
H16 | 0.2394 | 0.2733 | 0.7520 | 0.066* | |
C17 | 0.3681 (3) | 0.4349 (3) | 0.7299 (2) | 0.0473 (9) | |
C18 | 0.6431 (3) | 0.7427 (3) | 0.5268 (2) | 0.0540 (10) | |
H18A | 0.5972 | 0.6563 | 0.5244 | 0.054* | |
H18B | 0.6906 | 0.7571 | 0.4785 | 0.054* | |
C19 | 0.7901 (3) | 0.7123 (3) | 0.6659 (2) | 0.0536 (10) | |
H19A | 0.7268 | 0.6292 | 0.6498 | 0.054* | |
H19B | 0.8629 | 0.7198 | 0.6420 | 0.054* | |
C20 | 0.8322 (3) | 0.7469 (3) | 0.7714 (2) | 0.0460 (9) | |
C21 | 0.8445 (3) | 0.8192 (3) | 0.9129 (2) | 0.0395 (8) | |
C22 | 0.8318 (3) | 0.8758 (3) | 0.9918 (2) | 0.0491 (9) | |
H22 | 0.7748 | 0.9118 | 0.9852 | 0.049* | |
C23 | 0.9073 (3) | 0.8763 (3) | 1.0803 (3) | 0.0588 (10) | |
H23 | 0.9020 | 0.9142 | 1.1346 | 0.059* | |
C24 | 0.9911 (4) | 0.8212 (4) | 1.0896 (3) | 0.0661 (12) | |
H24 | 1.0398 | 0.8221 | 1.1506 | 0.066* | |
C25 | 1.0046 (3) | 0.7656 (3) | 1.0125 (3) | 0.0611 (11) | |
H25 | 1.0611 | 0.7288 | 1.0198 | 0.061* | |
C26 | 0.9304 (3) | 0.7663 (3) | 0.9228 (3) | 0.0465 (9) | |
C27 | 0.8365 (3) | 0.9144 (3) | 0.6219 (2) | 0.0510 (9) | |
H27A | 0.9159 | 0.9234 | 0.6669 | 0.051* | |
H27B | 0.8510 | 0.9210 | 0.5586 | 0.051* | |
C28 | 0.8011 (3) | 1.0120 (3) | 0.6487 (2) | 0.0450 (8) | |
C29 | 0.7120 (3) | 1.1080 (3) | 0.7109 (2) | 0.0408 (8) | |
C30 | 0.6405 (3) | 1.1445 (3) | 0.7569 (2) | 0.0509 (9) | |
H30 | 0.5814 | 1.0905 | 0.7851 | 0.051* | |
C31 | 0.6591 (4) | 1.2636 (3) | 0.7597 (3) | 0.0621 (11) | |
H31 | 0.6127 | 1.2904 | 0.7911 | 0.062* | |
C32 | 0.7462 (4) | 1.3442 (3) | 0.7164 (3) | 0.0657 (11) | |
H32 | 0.7564 | 1.4238 | 0.7195 | 0.066* | |
C33 | 0.8176 (4) | 1.3096 (3) | 0.6693 (3) | 0.0580 (10) | |
H33 | 0.8754 | 1.3634 | 0.6400 | 0.058* | |
C34 | 0.7989 (3) | 1.1914 (3) | 0.6680 (2) | 0.0454 (9) | |
C35 | 0.1333 (5) | 0.5574 (5) | 0.7902 (5) | 0.110 (2) | |
H35A | 0.2206 | 0.6119 | 0.7918 | 0.110* | |
H35B | 0.1086 | 0.4858 | 0.7460 | 0.110* | |
C36 | 0.1282 (7) | 0.5245 (6) | 0.8845 (5) | 0.171 (3) | |
H36A | 0.1639 | 0.5962 | 0.9299 | 0.171* | |
H36B | 0.1769 | 0.4778 | 0.9019 | 0.171* | |
H36C | 0.0405 | 0.4778 | 0.8845 | 0.171* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Zn | 0.0348 (2) | 0.0475 (2) | 0.0385 (2) | 0.01769 (19) | 0.00673 (18) | 0.01114 (18) |
N1 | 0.0425 (17) | 0.0457 (17) | 0.0384 (16) | 0.0171 (15) | 0.0089 (13) | 0.0099 (13) |
N2 | 0.0321 (15) | 0.0496 (17) | 0.0384 (16) | 0.0187 (14) | 0.0079 (13) | 0.0153 (13) |
N3 | 0.0395 (17) | 0.066 (2) | 0.0459 (18) | 0.0286 (16) | 0.0008 (14) | 0.0098 (15) |
N4 | 0.0430 (17) | 0.0454 (17) | 0.0404 (17) | 0.0158 (14) | 0.0061 (14) | 0.0104 (13) |
N5 | 0.0403 (17) | 0.0479 (18) | 0.0514 (19) | 0.0115 (15) | 0.0015 (14) | 0.0038 (14) |
N6 | 0.0466 (17) | 0.0519 (18) | 0.0368 (16) | 0.0233 (15) | 0.0103 (14) | 0.0062 (13) |
N7 | 0.0392 (16) | 0.0493 (17) | 0.0403 (16) | 0.0228 (14) | 0.0076 (13) | 0.0072 (13) |
N8 | 0.0455 (18) | 0.064 (2) | 0.062 (2) | 0.0346 (16) | 0.0119 (16) | 0.0145 (17) |
N9 | 0.0384 (16) | 0.0494 (18) | 0.0371 (16) | 0.0158 (14) | 0.0132 (13) | 0.0089 (13) |
N10 | 0.0395 (17) | 0.0564 (19) | 0.0458 (17) | 0.0105 (15) | 0.0190 (14) | 0.0150 (15) |
N11 | 0.052 (2) | 0.088 (3) | 0.055 (2) | 0.035 (2) | 0.0105 (18) | 0.014 (2) |
N12 | 0.063 (2) | 0.056 (2) | 0.066 (2) | 0.024 (2) | 0.015 (2) | 0.0019 (19) |
O1 | 0.132 (3) | 0.163 (3) | 0.072 (2) | 0.117 (3) | 0.046 (2) | 0.049 (2) |
O2 | 0.074 (2) | 0.175 (3) | 0.0592 (19) | 0.059 (2) | 0.0262 (17) | 0.048 (2) |
O3 | 0.087 (2) | 0.101 (2) | 0.091 (2) | 0.058 (2) | 0.0290 (18) | 0.0227 (18) |
O4 | 0.056 (2) | 0.121 (3) | 0.110 (3) | 0.023 (2) | −0.0222 (19) | −0.021 (2) |
O5 | 0.076 (2) | 0.098 (2) | 0.082 (2) | 0.0251 (18) | 0.0147 (18) | 0.0370 (19) |
O6 | 0.091 (2) | 0.073 (2) | 0.084 (2) | 0.0159 (19) | 0.0373 (19) | 0.0166 (17) |
O7 | 0.094 (2) | 0.099 (2) | 0.084 (2) | 0.062 (2) | 0.019 (2) | 0.007 (2) |
C1 | 0.052 (2) | 0.063 (2) | 0.0311 (19) | 0.021 (2) | 0.0055 (17) | 0.0080 (17) |
C2 | 0.043 (2) | 0.060 (2) | 0.036 (2) | 0.0214 (19) | 0.0035 (16) | 0.0119 (17) |
C3 | 0.0314 (19) | 0.046 (2) | 0.041 (2) | 0.0149 (17) | 0.0080 (16) | 0.0075 (16) |
C4 | 0.0310 (18) | 0.0399 (19) | 0.042 (2) | 0.0099 (16) | 0.0111 (16) | 0.0119 (15) |
C5 | 0.042 (2) | 0.057 (2) | 0.042 (2) | 0.0207 (18) | 0.0159 (17) | 0.0170 (17) |
C6 | 0.057 (2) | 0.060 (2) | 0.045 (2) | 0.020 (2) | 0.017 (2) | 0.0168 (18) |
C7 | 0.052 (2) | 0.067 (3) | 0.051 (2) | 0.020 (2) | 0.026 (2) | 0.0035 (19) |
C8 | 0.043 (2) | 0.065 (3) | 0.069 (3) | 0.026 (2) | 0.017 (2) | 0.004 (2) |
C9 | 0.0315 (19) | 0.050 (2) | 0.043 (2) | 0.0149 (17) | 0.0113 (16) | 0.0057 (16) |
C10 | 0.044 (2) | 0.059 (2) | 0.038 (2) | 0.0170 (19) | 0.0010 (17) | 0.0078 (17) |
C11 | 0.043 (2) | 0.045 (2) | 0.038 (2) | 0.0159 (18) | 0.0061 (17) | 0.0042 (16) |
C12 | 0.042 (2) | 0.043 (2) | 0.043 (2) | 0.0160 (18) | 0.0108 (17) | 0.0072 (16) |
C13 | 0.049 (2) | 0.048 (2) | 0.055 (2) | 0.0189 (18) | 0.0087 (19) | 0.0106 (18) |
C14 | 0.059 (3) | 0.058 (2) | 0.055 (2) | 0.026 (2) | 0.008 (2) | 0.020 (2) |
C15 | 0.067 (3) | 0.066 (3) | 0.072 (3) | 0.022 (2) | 0.017 (2) | 0.032 (2) |
C16 | 0.052 (2) | 0.047 (2) | 0.080 (3) | 0.004 (2) | 0.011 (2) | 0.015 (2) |
C17 | 0.041 (2) | 0.045 (2) | 0.051 (2) | 0.0151 (18) | 0.0081 (18) | 0.0052 (17) |
C18 | 0.055 (2) | 0.064 (2) | 0.040 (2) | 0.023 (2) | 0.0098 (18) | 0.0021 (18) |
C19 | 0.057 (2) | 0.062 (2) | 0.052 (2) | 0.035 (2) | 0.0144 (19) | 0.0075 (19) |
C20 | 0.039 (2) | 0.053 (2) | 0.050 (2) | 0.0239 (18) | 0.0099 (18) | 0.0144 (18) |
C21 | 0.0305 (18) | 0.0388 (19) | 0.040 (2) | 0.0081 (16) | 0.0041 (16) | 0.0094 (15) |
C22 | 0.036 (2) | 0.056 (2) | 0.047 (2) | 0.0132 (18) | 0.0073 (17) | 0.0085 (18) |
C23 | 0.049 (2) | 0.070 (3) | 0.043 (2) | 0.014 (2) | 0.0062 (19) | 0.0057 (19) |
C24 | 0.050 (3) | 0.083 (3) | 0.045 (2) | 0.017 (2) | −0.005 (2) | 0.019 (2) |
C25 | 0.040 (2) | 0.074 (3) | 0.065 (3) | 0.026 (2) | 0.002 (2) | 0.020 (2) |
C26 | 0.0328 (19) | 0.054 (2) | 0.051 (2) | 0.0166 (17) | 0.0097 (17) | 0.0165 (18) |
C27 | 0.045 (2) | 0.068 (3) | 0.044 (2) | 0.024 (2) | 0.0184 (18) | 0.0144 (18) |
C28 | 0.040 (2) | 0.054 (2) | 0.0343 (19) | 0.0143 (18) | 0.0071 (16) | 0.0059 (16) |
C29 | 0.039 (2) | 0.044 (2) | 0.0322 (18) | 0.0111 (17) | 0.0068 (16) | 0.0053 (15) |
C30 | 0.053 (2) | 0.049 (2) | 0.046 (2) | 0.0146 (19) | 0.0161 (19) | 0.0081 (17) |
C31 | 0.078 (3) | 0.057 (3) | 0.053 (2) | 0.030 (2) | 0.021 (2) | 0.002 (2) |
C32 | 0.080 (3) | 0.040 (2) | 0.063 (3) | 0.017 (2) | 0.008 (2) | 0.0034 (19) |
C33 | 0.057 (3) | 0.050 (2) | 0.053 (2) | 0.009 (2) | 0.015 (2) | 0.0110 (19) |
C34 | 0.041 (2) | 0.049 (2) | 0.035 (2) | 0.0112 (18) | 0.0020 (16) | 0.0079 (16) |
C35 | 0.070 (4) | 0.081 (4) | 0.169 (6) | 0.038 (3) | 0.005 (4) | −0.007 (4) |
C36 | 0.187 (8) | 0.129 (6) | 0.186 (8) | 0.079 (5) | 0.001 (6) | 0.059 (5) |
Zn—N2 | 2.033 (3) | C7—C8 | 1.361 (5) |
Zn—N7 | 2.064 (3) | C7—H7 | 0.9300 |
Zn—N9 | 2.163 (3) | C8—C9 | 1.396 (5) |
Zn—N4 | 2.178 (3) | C8—H8A | 0.9300 |
Zn—N6 | 2.240 (3) | C10—C11 | 1.491 (4) |
Zn—N1 | 2.344 (3) | C10—H10A | 0.9700 |
N1—C2 | 1.469 (4) | C10—H10B | 0.9700 |
N1—C1 | 1.474 (4) | C12—C13 | 1.381 (4) |
N1—C10 | 1.480 (4) | C12—C17 | 1.396 (4) |
N2—C3 | 1.317 (4) | C13—C14 | 1.369 (4) |
N2—C4 | 1.400 (4) | C13—H13 | 0.9300 |
N3—C3 | 1.328 (4) | C14—C15 | 1.379 (5) |
N3—C9 | 1.380 (4) | C14—H14 | 0.9300 |
N3—H3 | 0.8600 | C15—C16 | 1.367 (5) |
N4—C11 | 1.307 (4) | C15—H15 | 0.9300 |
N4—C12 | 1.399 (4) | C16—C17 | 1.391 (4) |
N5—C11 | 1.345 (4) | C16—H16 | 0.9300 |
N5—C17 | 1.376 (4) | C18—H18A | 0.9700 |
N5—H5 | 0.8600 | C18—H18B | 0.9700 |
N6—C18 | 1.470 (4) | C19—C20 | 1.483 (5) |
N6—C19 | 1.484 (4) | C19—H19A | 0.9700 |
N6—C27 | 1.488 (4) | C19—H19B | 0.9700 |
N7—C20 | 1.323 (4) | C21—C22 | 1.388 (5) |
N7—C21 | 1.395 (4) | C21—C26 | 1.388 (4) |
N8—C20 | 1.339 (4) | C22—C23 | 1.375 (4) |
N8—C26 | 1.372 (4) | C22—H22 | 0.9300 |
N8—H8 | 0.8600 | C23—C24 | 1.387 (5) |
N9—C28 | 1.324 (4) | C23—H23 | 0.9300 |
N9—C29 | 1.397 (4) | C24—C25 | 1.366 (5) |
N10—C28 | 1.346 (4) | C24—H24 | 0.9300 |
N10—C34 | 1.391 (4) | C25—C26 | 1.388 (5) |
N10—H10 | 0.8600 | C25—H25 | 0.9300 |
N11—O2 | 1.227 (4) | C27—C28 | 1.483 (5) |
N11—O3 | 1.230 (4) | C27—H27A | 0.9700 |
N11—O1 | 1.244 (4) | C27—H27B | 0.9700 |
N12—O5 | 1.230 (4) | C29—C30 | 1.379 (5) |
N12—O4 | 1.230 (4) | C29—C34 | 1.401 (4) |
N12—O6 | 1.235 (4) | C30—C31 | 1.380 (5) |
O7—C35 | 1.391 (5) | C30—H30 | 0.9300 |
O7—H7A | 0.849 (19) | C31—C32 | 1.391 (5) |
C1—C18 | 1.521 (5) | C31—H31 | 0.9300 |
C1—H1A | 0.9700 | C32—C33 | 1.375 (5) |
C1—H1B | 0.9700 | C32—H32 | 0.9300 |
C2—C3 | 1.495 (4) | C33—C34 | 1.370 (5) |
C2—H2A | 0.9700 | C33—H33 | 0.9300 |
C2—H2B | 0.9700 | C35—C36 | 1.439 (7) |
C4—C5 | 1.380 (4) | C35—H35A | 0.9700 |
C4—C9 | 1.387 (4) | C35—H35B | 0.9700 |
C5—C6 | 1.377 (4) | C36—H36A | 0.9600 |
C5—H5A | 0.9300 | C36—H36B | 0.9600 |
C6—C7 | 1.396 (5) | C36—H36C | 0.9600 |
C6—H6 | 0.9300 | ||
N2—Zn—N7 | 126.89 (11) | C11—C10—H10B | 109.1 |
N2—Zn—N9 | 93.32 (10) | H10A—C10—H10B | 107.8 |
N7—Zn—N9 | 97.35 (10) | N4—C11—N5 | 112.5 (3) |
N2—Zn—N4 | 88.93 (11) | N4—C11—C10 | 124.1 (3) |
N7—Zn—N4 | 94.27 (10) | N5—C11—C10 | 123.4 (3) |
N9—Zn—N4 | 163.56 (9) | C13—C12—C17 | 119.6 (3) |
N2—Zn—N6 | 154.65 (10) | C13—C12—N4 | 131.7 (3) |
N7—Zn—N6 | 78.23 (11) | C17—C12—N4 | 108.6 (3) |
N9—Zn—N6 | 78.38 (10) | C14—C13—C12 | 117.9 (3) |
N4—Zn—N6 | 92.72 (11) | C14—C13—H13 | 121.0 |
N2—Zn—N1 | 76.88 (10) | C12—C13—H13 | 121.0 |
N7—Zn—N1 | 154.97 (10) | C13—C14—C15 | 122.3 (4) |
N9—Zn—N1 | 87.86 (10) | C13—C14—H14 | 118.9 |
N4—Zn—N1 | 76.79 (10) | C15—C14—H14 | 118.9 |
N6—Zn—N1 | 78.90 (10) | C16—C15—C14 | 121.2 (4) |
C2—N1—C1 | 116.1 (2) | C16—C15—H15 | 119.4 |
C2—N1—C10 | 111.6 (3) | C14—C15—H15 | 119.4 |
C1—N1—C10 | 112.1 (3) | C15—C16—C17 | 116.9 (3) |
C2—N1—Zn | 101.61 (18) | C15—C16—H16 | 121.5 |
C1—N1—Zn | 104.58 (19) | C17—C16—H16 | 121.5 |
C10—N1—Zn | 109.89 (18) | N5—C17—C16 | 132.6 (3) |
C3—N2—C4 | 105.7 (3) | N5—C17—C12 | 105.3 (3) |
C3—N2—Zn | 114.4 (2) | C16—C17—C12 | 122.1 (3) |
C4—N2—Zn | 139.5 (2) | N6—C18—C1 | 111.0 (3) |
C3—N3—C9 | 108.3 (3) | N6—C18—H18A | 109.4 |
C3—N3—H3 | 125.9 | C1—C18—H18A | 109.4 |
C9—N3—H3 | 125.9 | N6—C18—H18B | 109.4 |
C11—N4—C12 | 105.7 (3) | C1—C18—H18B | 109.4 |
C11—N4—Zn | 114.4 (2) | H18A—C18—H18B | 108.0 |
C12—N4—Zn | 134.9 (2) | C20—C19—N6 | 108.1 (3) |
C11—N5—C17 | 107.9 (3) | C20—C19—H19A | 110.1 |
C11—N5—H5 | 126.1 | N6—C19—H19A | 110.1 |
C17—N5—H5 | 126.1 | C20—C19—H19B | 110.1 |
C18—N6—C19 | 113.7 (3) | N6—C19—H19B | 110.1 |
C18—N6—C27 | 112.4 (3) | H19A—C19—H19B | 108.4 |
C19—N6—C27 | 110.5 (3) | N7—C20—N8 | 112.7 (3) |
C18—N6—Zn | 108.2 (2) | N7—C20—C19 | 122.3 (3) |
C19—N6—Zn | 102.61 (19) | N8—C20—C19 | 124.9 (3) |
C27—N6—Zn | 108.9 (2) | C22—C21—C26 | 121.4 (3) |
C20—N7—C21 | 105.3 (3) | C22—C21—N7 | 130.1 (3) |
C20—N7—Zn | 111.0 (2) | C26—C21—N7 | 108.5 (3) |
C21—N7—Zn | 142.5 (2) | C23—C22—C21 | 117.2 (3) |
C20—N8—C26 | 107.2 (3) | C23—C22—H22 | 121.4 |
C20—N8—H8 | 126.4 | C21—C22—H22 | 121.4 |
C26—N8—H8 | 126.4 | C22—C23—C24 | 121.0 (4) |
C28—N9—C29 | 105.0 (3) | C22—C23—H23 | 119.5 |
C28—N9—Zn | 113.2 (2) | C24—C23—H23 | 119.5 |
C29—N9—Zn | 141.8 (2) | C25—C24—C23 | 122.3 (4) |
C28—N10—C34 | 108.0 (3) | C25—C24—H24 | 118.9 |
C28—N10—H10 | 126.0 | C23—C24—H24 | 118.9 |
C34—N10—H10 | 126.0 | C24—C25—C26 | 117.1 (4) |
O2—N11—O3 | 121.3 (4) | C24—C25—H25 | 121.4 |
O2—N11—O1 | 119.1 (4) | C26—C25—H25 | 121.4 |
O3—N11—O1 | 119.5 (3) | N8—C26—C25 | 132.7 (3) |
O5—N12—O4 | 119.1 (4) | N8—C26—C21 | 106.3 (3) |
O5—N12—O6 | 118.9 (4) | C25—C26—C21 | 120.9 (4) |
O4—N12—O6 | 122.0 (4) | C28—C27—N6 | 111.1 (3) |
C35—O7—H7A | 115 (4) | C28—C27—H27A | 109.4 |
N1—C1—C18 | 110.3 (3) | N6—C27—H27A | 109.4 |
N1—C1—H1A | 109.6 | C28—C27—H27B | 109.4 |
C18—C1—H1A | 109.6 | N6—C27—H27B | 109.4 |
N1—C1—H1B | 109.6 | H27A—C27—H27B | 108.0 |
C18—C1—H1B | 109.6 | N9—C28—N10 | 112.7 (3) |
H1A—C1—H1B | 108.1 | N9—C28—C27 | 122.5 (3) |
N1—C2—C3 | 108.4 (3) | N10—C28—C27 | 124.8 (3) |
N1—C2—H2A | 110.0 | C30—C29—N9 | 130.7 (3) |
C3—C2—H2A | 110.0 | C30—C29—C34 | 119.5 (3) |
N1—C2—H2B | 110.0 | N9—C29—C34 | 109.8 (3) |
C3—C2—H2B | 110.0 | C29—C30—C31 | 118.0 (3) |
H2A—C2—H2B | 108.4 | C29—C30—H30 | 121.0 |
N2—C3—N3 | 112.2 (3) | C31—C30—H30 | 121.0 |
N2—C3—C2 | 121.8 (3) | C30—C31—C32 | 121.1 (4) |
N3—C3—C2 | 125.9 (3) | C30—C31—H31 | 119.5 |
C5—C4—C9 | 122.0 (3) | C32—C31—H31 | 119.5 |
C5—C4—N2 | 129.5 (3) | C33—C32—C31 | 122.0 (4) |
C9—C4—N2 | 108.4 (3) | C33—C32—H32 | 119.0 |
C6—C5—C4 | 116.5 (3) | C31—C32—H32 | 119.0 |
C6—C5—H5A | 121.7 | C34—C33—C32 | 116.2 (4) |
C4—C5—H5A | 121.7 | C34—C33—H33 | 121.9 |
C5—C6—C7 | 121.5 (3) | C32—C33—H33 | 121.9 |
C5—C6—H6 | 119.3 | C33—C34—N10 | 132.3 (3) |
C7—C6—H6 | 119.3 | C33—C34—C29 | 123.2 (4) |
C8—C7—C6 | 122.2 (4) | N10—C34—C29 | 104.5 (3) |
C8—C7—H7 | 118.9 | O7—C35—C36 | 111.0 (5) |
C6—C7—H7 | 118.9 | O7—C35—H35A | 109.4 |
C7—C8—C9 | 116.6 (3) | C36—C35—H35A | 109.4 |
C7—C8—H8A | 121.7 | O7—C35—H35B | 109.4 |
C9—C8—H8A | 121.7 | C36—C35—H35B | 109.4 |
N3—C9—C4 | 105.4 (3) | H35A—C35—H35B | 108.0 |
N3—C9—C8 | 133.6 (3) | C35—C36—H36A | 109.5 |
C4—C9—C8 | 121.1 (3) | C35—C36—H36B | 109.5 |
N1—C10—C11 | 112.6 (3) | H36A—C36—H36B | 109.5 |
N1—C10—H10A | 109.1 | C35—C36—H36C | 109.5 |
C11—C10—H10A | 109.1 | H36A—C36—H36C | 109.5 |
N1—C10—H10B | 109.1 | H36B—C36—H36C | 109.5 |
N2—Zn—N1—C2 | 34.61 (19) | C5—C4—C9—N3 | −176.5 (3) |
N7—Zn—N1—C2 | −162.2 (2) | N2—C4—C9—N3 | 1.1 (3) |
N9—Zn—N1—C2 | −59.30 (19) | C5—C4—C9—C8 | 2.2 (5) |
N4—Zn—N1—C2 | 126.6 (2) | N2—C4—C9—C8 | 179.8 (3) |
N6—Zn—N1—C2 | −137.9 (2) | C7—C8—C9—N3 | 177.3 (4) |
N2—Zn—N1—C1 | 155.8 (2) | C7—C8—C9—C4 | −1.0 (5) |
N7—Zn—N1—C1 | −41.0 (3) | C2—N1—C10—C11 | −115.1 (3) |
N9—Zn—N1—C1 | 61.9 (2) | C1—N1—C10—C11 | 112.7 (3) |
N4—Zn—N1—C1 | −112.2 (2) | Zn—N1—C10—C11 | −3.1 (3) |
N6—Zn—N1—C1 | −16.7 (2) | C12—N4—C11—N5 | −1.1 (4) |
N2—Zn—N1—C10 | −83.7 (2) | Zn—N4—C11—N5 | −160.0 (2) |
N7—Zn—N1—C10 | 79.5 (3) | C12—N4—C11—C10 | 176.1 (3) |
N9—Zn—N1—C10 | −177.6 (2) | Zn—N4—C11—C10 | 17.2 (4) |
N4—Zn—N1—C10 | 8.3 (2) | C17—N5—C11—N4 | 1.3 (4) |
N6—Zn—N1—C10 | 103.8 (2) | C17—N5—C11—C10 | −175.8 (3) |
N7—Zn—N2—C3 | 166.2 (2) | N1—C10—C11—N4 | −9.1 (5) |
N9—Zn—N2—C3 | 64.4 (2) | N1—C10—C11—N5 | 167.7 (3) |
N4—Zn—N2—C3 | −99.3 (2) | C11—N4—C12—C13 | −176.4 (4) |
N6—Zn—N2—C3 | −5.2 (4) | Zn—N4—C12—C13 | −23.9 (6) |
N1—Zn—N2—C3 | −22.6 (2) | C11—N4—C12—C17 | 0.4 (4) |
N7—Zn—N2—C4 | −5.0 (4) | Zn—N4—C12—C17 | 152.9 (3) |
N9—Zn—N2—C4 | −106.7 (3) | C17—C12—C13—C14 | −0.1 (5) |
N4—Zn—N2—C4 | 89.5 (3) | N4—C12—C13—C14 | 176.4 (3) |
N6—Zn—N2—C4 | −176.3 (3) | C12—C13—C14—C15 | −0.2 (6) |
N1—Zn—N2—C4 | 166.2 (3) | C13—C14—C15—C16 | 0.6 (7) |
N2—Zn—N4—C11 | 63.6 (2) | C14—C15—C16—C17 | −0.7 (6) |
N7—Zn—N4—C11 | −169.5 (2) | C11—N5—C17—C16 | 176.3 (4) |
N9—Zn—N4—C11 | −34.5 (5) | C11—N5—C17—C12 | −1.0 (4) |
N6—Zn—N4—C11 | −91.1 (2) | C15—C16—C17—N5 | −176.5 (4) |
N1—Zn—N4—C11 | −13.2 (2) | C15—C16—C17—C12 | 0.5 (6) |
N2—Zn—N4—C12 | −87.1 (3) | C13—C12—C17—N5 | 177.6 (3) |
N7—Zn—N4—C12 | 39.8 (3) | N4—C12—C17—N5 | 0.4 (4) |
N9—Zn—N4—C12 | 174.7 (3) | C13—C12—C17—C16 | −0.1 (6) |
N6—Zn—N4—C12 | 118.2 (3) | N4—C12—C17—C16 | −177.3 (3) |
N1—Zn—N4—C12 | −163.9 (3) | C19—N6—C18—C1 | 155.1 (3) |
N2—Zn—N6—C18 | −30.4 (3) | C27—N6—C18—C1 | −78.5 (3) |
N7—Zn—N6—C18 | 156.6 (2) | Zn—N6—C18—C1 | 41.8 (3) |
N9—Zn—N6—C18 | −103.2 (2) | N1—C1—C18—N6 | −60.9 (4) |
N4—Zn—N6—C18 | 62.8 (2) | C18—N6—C19—C20 | −156.5 (3) |
N1—Zn—N6—C18 | −13.2 (2) | C27—N6—C19—C20 | 76.0 (3) |
N2—Zn—N6—C19 | −150.9 (2) | Zn—N6—C19—C20 | −39.9 (3) |
N7—Zn—N6—C19 | 36.1 (2) | C21—N7—C20—N8 | 0.7 (4) |
N9—Zn—N6—C19 | 136.3 (2) | Zn—N7—C20—N8 | −169.7 (2) |
N4—Zn—N6—C19 | −57.7 (2) | C21—N7—C20—C19 | 179.5 (3) |
N1—Zn—N6—C19 | −133.6 (2) | Zn—N7—C20—C19 | 9.1 (4) |
N2—Zn—N6—C27 | 92.0 (3) | C26—N8—C20—N7 | 0.5 (4) |
N7—Zn—N6—C27 | −81.0 (2) | C26—N8—C20—C19 | −178.3 (3) |
N9—Zn—N6—C27 | 19.20 (19) | N6—C19—C20—N7 | 24.0 (4) |
N4—Zn—N6—C27 | −174.8 (2) | N6—C19—C20—N8 | −157.3 (3) |
N1—Zn—N6—C27 | 109.3 (2) | C20—N7—C21—C22 | 178.2 (3) |
N2—Zn—N7—C20 | 158.5 (2) | Zn—N7—C21—C22 | −16.6 (6) |
N9—Zn—N7—C20 | −101.7 (2) | C20—N7—C21—C26 | −1.6 (3) |
N4—Zn—N7—C20 | 66.6 (2) | Zn—N7—C21—C26 | 163.5 (3) |
N6—Zn—N7—C20 | −25.3 (2) | C26—C21—C22—C23 | −0.5 (5) |
N1—Zn—N7—C20 | −0.9 (4) | N7—C21—C22—C23 | 179.6 (3) |
N2—Zn—N7—C21 | −6.2 (4) | C21—C22—C23—C24 | −0.7 (5) |
N9—Zn—N7—C21 | 93.6 (3) | C22—C23—C24—C25 | 1.0 (6) |
N4—Zn—N7—C21 | −98.0 (3) | C23—C24—C25—C26 | 0.1 (6) |
N6—Zn—N7—C21 | 170.1 (4) | C20—N8—C26—C25 | 179.0 (4) |
N1—Zn—N7—C21 | −165.6 (3) | C20—N8—C26—C21 | −1.5 (4) |
N2—Zn—N9—C28 | −164.5 (2) | C24—C25—C26—N8 | 178.1 (4) |
N7—Zn—N9—C28 | 67.7 (2) | C24—C25—C26—C21 | −1.4 (5) |
N4—Zn—N9—C28 | −67.0 (5) | C22—C21—C26—N8 | −178.0 (3) |
N6—Zn—N9—C28 | −8.7 (2) | N7—C21—C26—N8 | 1.9 (3) |
N1—Zn—N9—C28 | −87.8 (2) | C22—C21—C26—C25 | 1.6 (5) |
N2—Zn—N9—C29 | 11.5 (3) | N7—C21—C26—C25 | −178.5 (3) |
N7—Zn—N9—C29 | −116.3 (3) | C18—N6—C27—C28 | 93.6 (3) |
N4—Zn—N9—C29 | 109.0 (5) | C19—N6—C27—C28 | −138.2 (3) |
N6—Zn—N9—C29 | 167.4 (3) | Zn—N6—C27—C28 | −26.2 (3) |
N1—Zn—N9—C29 | 88.2 (3) | C29—N9—C28—N10 | −0.2 (3) |
C2—N1—C1—C18 | 155.0 (3) | Zn—N9—C28—N10 | 177.3 (2) |
C10—N1—C1—C18 | −75.0 (3) | C29—N9—C28—C27 | 178.1 (3) |
Zn—N1—C1—C18 | 44.0 (3) | Zn—N9—C28—C27 | −4.4 (4) |
C1—N1—C2—C3 | −152.3 (3) | C34—N10—C28—N9 | 0.0 (4) |
C10—N1—C2—C3 | 77.5 (3) | C34—N10—C28—C27 | −178.2 (3) |
Zn—N1—C2—C3 | −39.6 (3) | N6—C27—C28—N9 | 21.8 (4) |
C4—N2—C3—N3 | 1.4 (4) | N6—C27—C28—N10 | −160.1 (3) |
Zn—N2—C3—N3 | −172.7 (2) | C28—N9—C29—C30 | −179.9 (3) |
C4—N2—C3—C2 | 180.0 (3) | Zn—N9—C29—C30 | 3.9 (6) |
Zn—N2—C3—C2 | 5.9 (4) | C28—N9—C29—C34 | 0.2 (3) |
C9—N3—C3—N2 | −0.7 (4) | Zn—N9—C29—C34 | −176.0 (2) |
C9—N3—C3—C2 | −179.2 (3) | N9—C29—C30—C31 | 179.3 (3) |
N1—C2—C3—N2 | 27.5 (4) | C34—C29—C30—C31 | −0.8 (5) |
N1—C2—C3—N3 | −154.2 (3) | C29—C30—C31—C32 | 0.9 (5) |
C3—N2—C4—C5 | 175.8 (3) | C30—C31—C32—C33 | −0.2 (6) |
Zn—N2—C4—C5 | −12.6 (6) | C31—C32—C33—C34 | −0.5 (6) |
C3—N2—C4—C9 | −1.5 (3) | C32—C33—C34—N10 | −179.1 (3) |
Zn—N2—C4—C9 | 170.1 (2) | C32—C33—C34—C29 | 0.5 (5) |
C9—C4—C5—C6 | −1.8 (5) | C28—N10—C34—C33 | 179.8 (4) |
N2—C4—C5—C6 | −178.8 (3) | C28—N10—C34—C29 | 0.1 (3) |
C4—C5—C6—C7 | 0.2 (5) | C30—C29—C34—C33 | 0.2 (5) |
C5—C6—C7—C8 | 1.0 (6) | N9—C29—C34—C33 | −179.9 (3) |
C6—C7—C8—C9 | −0.6 (5) | C30—C29—C34—N10 | 179.9 (3) |
C3—N3—C9—C4 | −0.3 (4) | N9—C29—C34—N10 | −0.2 (3) |
C3—N3—C9—C8 | −178.8 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3···O1i | 0.86 | 2.00 | 2.787 (4) | 152 |
N3—H3···O2i | 0.86 | 2.35 | 3.037 (4) | 137 |
N5—H5···O5 | 0.86 | 2.05 | 2.875 (4) | 160 |
N8—H8···O7ii | 0.86 | 1.91 | 2.762 (4) | 169 |
N10—H10···O5iii | 0.86 | 2.28 | 2.988 (4) | 140 |
O7—H7A···O4iv | 0.85 (2) | 2.26 (3) | 3.039 (5) | 152 (5) |
O7—H7A···O6iv | 0.85 (2) | 2.28 (3) | 3.049 (4) | 151 (5) |
Symmetry codes: (i) x, y+1, z; (ii) x+1, y, z; (iii) x+1, y+1, z; (iv) −x, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | [Zn(C34H32N10)](NO3)2·C2H6O |
Mr | 816.15 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 11.783 (3), 12.219 (4), 14.468 (6) |
α, β, γ (°) | 91.42 (3), 103.51 (3), 113.653 (18) |
V (Å3) | 1838.9 (11) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.74 |
Crystal size (mm) | 0.50 × 0.36 × 0.36 |
Data collection | |
Diffractometer | Siemens P4 diffractometer |
Absorption correction | Empirical (using intensity measurements) via ψ scan (North et al., 1968) |
Tmin, Tmax | 0.735, 0.768 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7751, 6479, 3961 |
Rint | 0.022 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.042, 0.089, 0.85 |
No. of reflections | 6479 |
No. of parameters | 509 |
No. of restraints | 2 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.26, −0.30 |
Computer programs: XSCANS (Siemens, 1994), XSCANS, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL-Plus (Sheldrick, 1990).
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3···O1i | 0.86 | 2.00 | 2.787 (4) | 152 |
N3—H3···O2i | 0.86 | 2.35 | 3.037 (4) | 137 |
N5—H5···O5 | 0.86 | 2.05 | 2.875 (4) | 160 |
N8—H8···O7ii | 0.86 | 1.91 | 2.762 (4) | 169 |
N10—H10···O5iii | 0.86 | 2.28 | 2.988 (4) | 140 |
O7—H7A···O4iv | 0.849 (19) | 2.26 (3) | 3.039 (5) | 152 (5) |
O7—H7A···O6iv | 0.849 (19) | 2.28 (3) | 3.049 (4) | 151 (5) |
Symmetry codes: (i) x, y+1, z; (ii) x+1, y, z; (iii) x+1, y+1, z; (iv) −x, −y+1, −z+1. |
N,N,N',N'-Tetrakis(2-benzimidazolylmethyl)-1,2-ethanediamine (EDTB) was first prepared by Reedijk et al. (1979) in order to investigate the relationships between the activity and structures of metalloproteins, such as hemocyanin, laccase, tyrosinase and superoxide dismutase (Hendriks et al., 1979). Nowaday, many complexes with EDTB and its derivatives have been synthesized and characterized, but only a few crystal structures of these complexes have been reported. [Cu(EDTB)(BF4)(BF3OC2H5)]·H2O shows a mononuclear structure, in which the CuII ion is coordinated by the six N atoms from one molecule of EDTB (Birker et al., 1981). The CuI complex, Cu2(EDTB)(ClO4)2, however, shows a dinuclear structure, in which each CuI ion is coordinated by two benzimidazole nitrogen atoms from one molecule of EDTB, and each EDTB is coordinated to two CuI ions (Hendriks et al., 1982). In a FeIII complex, EDTB shows an interesting coordination mode, two amine nitrogen atoms and three benzimidazole nitrogen atoms are coordinated to the same FeIII ion, while the remaining benzimidazole group is non-coordinating (Gomez-Romero et al., 1990). The structure of nickel complex with EDTB consists of the cationic species [Ni(EDTB)]2+, in which the NiII ion is six-coordinated by four benzimidazole nitrogen atoms and two amine nitrogen atoms (Holt et al., 1987). In this paper, the crystal structure of a zinc complex, (I), with EDTB is presented.
The structure of (I) is shown in Fig. 1 which consists of monomeric cationic species [Zn(EDTB)]2+ in which zinc ion is coordinated by four benzimidazole nitrogen atoms and two amine nitrogen atoms, forming five five-membered chelate rings. The coordination geometry around zinc ion can be described as distorted octahedral. The two zinc amine nitrogen distances, Zn—N1 [2.344 (3) Å] and Zn—N6 [2.240 (3) Å], are very similar to the values found for the other ZnII complexes with amine (Bu et al., 1996). The two distances Zn—N2 [2.033 (3) Å] and Zn—N7 [2.064 (3) Å] are very similar to the values found for other related ZnII complexes (Szlyk et al., 1997), while the other two Zn benzimidazole nitrogen distances, Zn—N4 [2.178 (3) Å] and Zn—N9 [2.163 (3) Å], are somewhat longer and presumably a consequence of the geometrical requirements of the ligand. The bond angles related to coordination sphere of ZnII ion range from 76.88 (10) to 126.89 (11)° for cis atoms and from 154.65 (10) to 163.56 (9)° for trans atoms. The largest deviation for ideal geometry is the cis N2—Zn—N7 angle of 126.89 (11)°. The phenyl and imidazole rings are planar, the deviation from the least-squares planes being less than 0.02 Å. Two non-coordinated nitrate ions are hydrogen bonded to benzimidazole N atoms and there is also a hydrogen bond between the ethanol molecule and the benzimidazole nitrogen atom. The data of hydrogen-bonding geometry are listed in Table 2.