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In the title compound, [Zn(EDTB)](NO3)2·C2H5OH, where EDTB = N,N,N',N'-tetrakis(2-benzimidazolyl­methyl)-1,2-ethanedi­amine (C34H32N10), the coordination geometry around each zinc ion can be described as distorted octahedral, with two equatorial benz­imidazole N atoms, two equatorial amine atoms, and two axial benz­imidazole N atoms. The nitrate anions do not coordinate to the zinc(II) cations, but act as counter-anions, and are hydrogen bonded to EDTB ligands.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803010602/ww6086sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803010602/ww6086Isup2.hkl
Contains datablock I

CCDC reference: 214789

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.042
  • wR factor = 0.089
  • Data-to-parameter ratio = 12.7

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








Comment top

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.

Experimental top

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).

Refinement top

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).

Computing details top

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).

Figures top
[Figure 1] Fig. 1. View of the local coordination of Zn(II) with the atomic numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. Packing diagram of (I)
(I) top
Crystal data top
[Zn(C34H32N10)](NO3)2·C2H6OZ = 2
Mr = 816.15F(000) = 848
Triclinic, P1Dx = 1.474 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 11.783 (3) ÅCell parameters from 33 reflections
b = 12.219 (4) Åθ = 5.3–10.4°
c = 14.468 (6) ŵ = 0.74 mm1
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
Data collection top
Siemens P4
diffractometer
3961 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.022
Graphite monochromatorθmax = 25.0°, θmin = 1.8°
ω scansh = 113
Absorption correction: empirical (using intensity measurements)
via ψ scan (North et al., 1968)
k = 1413
Tmin = 0.735, Tmax = 0.768l = 1716
7751 measured reflections3 standard reflections every 97 reflections
6479 independent reflections intensity decay: none
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.089H 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 parametersΔρmax = 0.26 e Å3
2 restraintsΔρmin = 0.30 e Å3
Crystal data top
[Zn(C34H32N10)](NO3)2·C2H6Oγ = 113.653 (18)°
Mr = 816.15V = 1838.9 (11) Å3
Triclinic, P1Z = 2
a = 11.783 (3) ÅMo Kα radiation
b = 12.219 (4) ŵ = 0.74 mm1
c = 14.468 (6) ÅT = 293 K
α = 91.42 (3)°0.50 × 0.36 × 0.36 mm
β = 103.51 (3)°
Data collection top
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 = 0.7683 standard reflections every 97 reflections
7751 measured reflections intensity decay: none
6479 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0422 restraints
wR(F2) = 0.089H atoms treated by a mixture of independent and constrained refinement
S = 0.85Δρmax = 0.26 e Å3
6479 reflectionsΔρmin = 0.30 e Å3
509 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Zn0.62262 (4)0.81089 (4)0.72370 (3)0.04054 (13)
N10.4715 (3)0.7750 (2)0.57566 (18)0.0429 (7)
N20.4776 (2)0.8363 (2)0.76022 (18)0.0396 (7)
N30.3193 (3)0.8921 (2)0.71996 (19)0.0502 (8)
H30.26330.91280.68490.050*
N40.5076 (3)0.6170 (2)0.70559 (19)0.0447 (7)
N50.3147 (3)0.4698 (2)0.6474 (2)0.0509 (8)
H50.23970.42930.60910.051*
N60.7335 (3)0.7936 (2)0.62202 (18)0.0443 (7)
N70.7814 (2)0.8038 (2)0.81595 (19)0.0420 (7)
N80.9218 (3)0.7230 (3)0.8318 (2)0.0538 (8)
H80.96580.68720.81640.054*
N90.7148 (2)0.9955 (2)0.69763 (18)0.0418 (7)
N100.8538 (3)1.1259 (3)0.62927 (19)0.0489 (7)
H100.91131.15340.59830.049*
N110.1498 (3)0.0462 (3)0.6324 (2)0.0640 (9)
N120.0151 (4)0.3603 (3)0.4818 (3)0.0628 (9)
O10.2134 (3)0.0127 (3)0.5903 (2)0.1001 (11)
O20.1349 (3)0.0107 (3)0.7092 (2)0.0984 (11)
O30.1032 (3)0.1141 (3)0.5965 (2)0.0852 (9)
O40.0973 (3)0.3112 (3)0.4333 (2)0.1096 (12)
O50.0443 (3)0.3317 (3)0.5619 (2)0.0896 (10)
O60.1000 (3)0.4364 (3)0.4520 (2)0.0861 (9)
O70.0516 (3)0.6129 (3)0.7580 (2)0.0861 (9)
H7A0.036 (5)0.618 (5)0.6984 (16)0.129*
C10.5474 (3)0.7990 (3)0.5047 (2)0.0511 (9)
H1A0.59310.88540.50620.051*
H1B0.49040.76590.44100.051*
C20.4172 (3)0.8612 (3)0.5902 (2)0.0476 (9)
H2A0.33410.83740.54440.048*
H2B0.47360.94100.58070.048*
C30.4029 (3)0.8627 (3)0.6901 (2)0.0404 (8)
C40.4365 (3)0.8471 (3)0.8419 (2)0.0387 (8)
C50.4772 (3)0.8227 (3)0.9332 (2)0.0459 (9)
H5A0.54200.79600.94920.046*
C60.4169 (3)0.8400 (3)0.9994 (3)0.0546 (10)
H60.44170.82491.06190.055*
C70.3193 (3)0.8797 (3)0.9748 (3)0.0561 (10)
H70.28180.89151.02180.056*
C80.2773 (3)0.9018 (3)0.8844 (3)0.0575 (10)
H8A0.21170.92760.86850.058*
C90.3375 (3)0.8839 (3)0.8168 (2)0.0420 (8)
C100.3733 (3)0.6490 (3)0.5592 (2)0.0506 (9)
H10A0.36960.60990.49870.051*
H10B0.28990.64910.55450.051*
C110.4005 (3)0.5784 (3)0.6372 (2)0.0435 (8)
C120.4904 (3)0.5279 (3)0.7665 (2)0.0434 (8)
C130.5679 (3)0.5220 (3)0.8523 (2)0.0522 (9)
H130.64980.58290.87790.052*
C140.5205 (4)0.4238 (3)0.8984 (3)0.0580 (10)
H140.57170.41860.95620.058*
C150.3994 (4)0.3323 (4)0.8622 (3)0.0700 (12)
H150.37070.26760.89620.070*
C160.3208 (4)0.3352 (3)0.7771 (3)0.0662 (11)
H160.23940.27330.75200.066*
C170.3681 (3)0.4349 (3)0.7299 (2)0.0473 (9)
C180.6431 (3)0.7427 (3)0.5268 (2)0.0540 (10)
H18A0.59720.65630.52440.054*
H18B0.69060.75710.47850.054*
C190.7901 (3)0.7123 (3)0.6659 (2)0.0536 (10)
H19A0.72680.62920.64980.054*
H19B0.86290.71980.64200.054*
C200.8322 (3)0.7469 (3)0.7714 (2)0.0460 (9)
C210.8445 (3)0.8192 (3)0.9129 (2)0.0395 (8)
C220.8318 (3)0.8758 (3)0.9918 (2)0.0491 (9)
H220.77480.91180.98520.049*
C230.9073 (3)0.8763 (3)1.0803 (3)0.0588 (10)
H230.90200.91421.13460.059*
C240.9911 (4)0.8212 (4)1.0896 (3)0.0661 (12)
H241.03980.82211.15060.066*
C251.0046 (3)0.7656 (3)1.0125 (3)0.0611 (11)
H251.06110.72881.01980.061*
C260.9304 (3)0.7663 (3)0.9228 (3)0.0465 (9)
C270.8365 (3)0.9144 (3)0.6219 (2)0.0510 (9)
H27A0.91590.92340.66690.051*
H27B0.85100.92100.55860.051*
C280.8011 (3)1.0120 (3)0.6487 (2)0.0450 (8)
C290.7120 (3)1.1080 (3)0.7109 (2)0.0408 (8)
C300.6405 (3)1.1445 (3)0.7569 (2)0.0509 (9)
H300.58141.09050.78510.051*
C310.6591 (4)1.2636 (3)0.7597 (3)0.0621 (11)
H310.61271.29040.79110.062*
C320.7462 (4)1.3442 (3)0.7164 (3)0.0657 (11)
H320.75641.42380.71950.066*
C330.8176 (4)1.3096 (3)0.6693 (3)0.0580 (10)
H330.87541.36340.64000.058*
C340.7989 (3)1.1914 (3)0.6680 (2)0.0454 (9)
C350.1333 (5)0.5574 (5)0.7902 (5)0.110 (2)
H35A0.22060.61190.79180.110*
H35B0.10860.48580.74600.110*
C360.1282 (7)0.5245 (6)0.8845 (5)0.171 (3)
H36A0.16390.59620.92990.171*
H36B0.17690.47780.90190.171*
H36C0.04050.47780.88450.171*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn0.0348 (2)0.0475 (2)0.0385 (2)0.01769 (19)0.00673 (18)0.01114 (18)
N10.0425 (17)0.0457 (17)0.0384 (16)0.0171 (15)0.0089 (13)0.0099 (13)
N20.0321 (15)0.0496 (17)0.0384 (16)0.0187 (14)0.0079 (13)0.0153 (13)
N30.0395 (17)0.066 (2)0.0459 (18)0.0286 (16)0.0008 (14)0.0098 (15)
N40.0430 (17)0.0454 (17)0.0404 (17)0.0158 (14)0.0061 (14)0.0104 (13)
N50.0403 (17)0.0479 (18)0.0514 (19)0.0115 (15)0.0015 (14)0.0038 (14)
N60.0466 (17)0.0519 (18)0.0368 (16)0.0233 (15)0.0103 (14)0.0062 (13)
N70.0392 (16)0.0493 (17)0.0403 (16)0.0228 (14)0.0076 (13)0.0072 (13)
N80.0455 (18)0.064 (2)0.062 (2)0.0346 (16)0.0119 (16)0.0145 (17)
N90.0384 (16)0.0494 (18)0.0371 (16)0.0158 (14)0.0132 (13)0.0089 (13)
N100.0395 (17)0.0564 (19)0.0458 (17)0.0105 (15)0.0190 (14)0.0150 (15)
N110.052 (2)0.088 (3)0.055 (2)0.035 (2)0.0105 (18)0.014 (2)
N120.063 (2)0.056 (2)0.066 (2)0.024 (2)0.015 (2)0.0019 (19)
O10.132 (3)0.163 (3)0.072 (2)0.117 (3)0.046 (2)0.049 (2)
O20.074 (2)0.175 (3)0.0592 (19)0.059 (2)0.0262 (17)0.048 (2)
O30.087 (2)0.101 (2)0.091 (2)0.058 (2)0.0290 (18)0.0227 (18)
O40.056 (2)0.121 (3)0.110 (3)0.023 (2)0.0222 (19)0.021 (2)
O50.076 (2)0.098 (2)0.082 (2)0.0251 (18)0.0147 (18)0.0370 (19)
O60.091 (2)0.073 (2)0.084 (2)0.0159 (19)0.0373 (19)0.0166 (17)
O70.094 (2)0.099 (2)0.084 (2)0.062 (2)0.019 (2)0.007 (2)
C10.052 (2)0.063 (2)0.0311 (19)0.021 (2)0.0055 (17)0.0080 (17)
C20.043 (2)0.060 (2)0.036 (2)0.0214 (19)0.0035 (16)0.0119 (17)
C30.0314 (19)0.046 (2)0.041 (2)0.0149 (17)0.0080 (16)0.0075 (16)
C40.0310 (18)0.0399 (19)0.042 (2)0.0099 (16)0.0111 (16)0.0119 (15)
C50.042 (2)0.057 (2)0.042 (2)0.0207 (18)0.0159 (17)0.0170 (17)
C60.057 (2)0.060 (2)0.045 (2)0.020 (2)0.017 (2)0.0168 (18)
C70.052 (2)0.067 (3)0.051 (2)0.020 (2)0.026 (2)0.0035 (19)
C80.043 (2)0.065 (3)0.069 (3)0.026 (2)0.017 (2)0.004 (2)
C90.0315 (19)0.050 (2)0.043 (2)0.0149 (17)0.0113 (16)0.0057 (16)
C100.044 (2)0.059 (2)0.038 (2)0.0170 (19)0.0010 (17)0.0078 (17)
C110.043 (2)0.045 (2)0.038 (2)0.0159 (18)0.0061 (17)0.0042 (16)
C120.042 (2)0.043 (2)0.043 (2)0.0160 (18)0.0108 (17)0.0072 (16)
C130.049 (2)0.048 (2)0.055 (2)0.0189 (18)0.0087 (19)0.0106 (18)
C140.059 (3)0.058 (2)0.055 (2)0.026 (2)0.008 (2)0.020 (2)
C150.067 (3)0.066 (3)0.072 (3)0.022 (2)0.017 (2)0.032 (2)
C160.052 (2)0.047 (2)0.080 (3)0.004 (2)0.011 (2)0.015 (2)
C170.041 (2)0.045 (2)0.051 (2)0.0151 (18)0.0081 (18)0.0052 (17)
C180.055 (2)0.064 (2)0.040 (2)0.023 (2)0.0098 (18)0.0021 (18)
C190.057 (2)0.062 (2)0.052 (2)0.035 (2)0.0144 (19)0.0075 (19)
C200.039 (2)0.053 (2)0.050 (2)0.0239 (18)0.0099 (18)0.0144 (18)
C210.0305 (18)0.0388 (19)0.040 (2)0.0081 (16)0.0041 (16)0.0094 (15)
C220.036 (2)0.056 (2)0.047 (2)0.0132 (18)0.0073 (17)0.0085 (18)
C230.049 (2)0.070 (3)0.043 (2)0.014 (2)0.0062 (19)0.0057 (19)
C240.050 (3)0.083 (3)0.045 (2)0.017 (2)0.005 (2)0.019 (2)
C250.040 (2)0.074 (3)0.065 (3)0.026 (2)0.002 (2)0.020 (2)
C260.0328 (19)0.054 (2)0.051 (2)0.0166 (17)0.0097 (17)0.0165 (18)
C270.045 (2)0.068 (3)0.044 (2)0.024 (2)0.0184 (18)0.0144 (18)
C280.040 (2)0.054 (2)0.0343 (19)0.0143 (18)0.0071 (16)0.0059 (16)
C290.039 (2)0.044 (2)0.0322 (18)0.0111 (17)0.0068 (16)0.0053 (15)
C300.053 (2)0.049 (2)0.046 (2)0.0146 (19)0.0161 (19)0.0081 (17)
C310.078 (3)0.057 (3)0.053 (2)0.030 (2)0.021 (2)0.002 (2)
C320.080 (3)0.040 (2)0.063 (3)0.017 (2)0.008 (2)0.0034 (19)
C330.057 (3)0.050 (2)0.053 (2)0.009 (2)0.015 (2)0.0110 (19)
C340.041 (2)0.049 (2)0.035 (2)0.0112 (18)0.0020 (16)0.0079 (16)
C350.070 (4)0.081 (4)0.169 (6)0.038 (3)0.005 (4)0.007 (4)
C360.187 (8)0.129 (6)0.186 (8)0.079 (5)0.001 (6)0.059 (5)
Geometric parameters (Å, º) top
Zn—N22.033 (3)C7—C81.361 (5)
Zn—N72.064 (3)C7—H70.9300
Zn—N92.163 (3)C8—C91.396 (5)
Zn—N42.178 (3)C8—H8A0.9300
Zn—N62.240 (3)C10—C111.491 (4)
Zn—N12.344 (3)C10—H10A0.9700
N1—C21.469 (4)C10—H10B0.9700
N1—C11.474 (4)C12—C131.381 (4)
N1—C101.480 (4)C12—C171.396 (4)
N2—C31.317 (4)C13—C141.369 (4)
N2—C41.400 (4)C13—H130.9300
N3—C31.328 (4)C14—C151.379 (5)
N3—C91.380 (4)C14—H140.9300
N3—H30.8600C15—C161.367 (5)
N4—C111.307 (4)C15—H150.9300
N4—C121.399 (4)C16—C171.391 (4)
N5—C111.345 (4)C16—H160.9300
N5—C171.376 (4)C18—H18A0.9700
N5—H50.8600C18—H18B0.9700
N6—C181.470 (4)C19—C201.483 (5)
N6—C191.484 (4)C19—H19A0.9700
N6—C271.488 (4)C19—H19B0.9700
N7—C201.323 (4)C21—C221.388 (5)
N7—C211.395 (4)C21—C261.388 (4)
N8—C201.339 (4)C22—C231.375 (4)
N8—C261.372 (4)C22—H220.9300
N8—H80.8600C23—C241.387 (5)
N9—C281.324 (4)C23—H230.9300
N9—C291.397 (4)C24—C251.366 (5)
N10—C281.346 (4)C24—H240.9300
N10—C341.391 (4)C25—C261.388 (5)
N10—H100.8600C25—H250.9300
N11—O21.227 (4)C27—C281.483 (5)
N11—O31.230 (4)C27—H27A0.9700
N11—O11.244 (4)C27—H27B0.9700
N12—O51.230 (4)C29—C301.379 (5)
N12—O41.230 (4)C29—C341.401 (4)
N12—O61.235 (4)C30—C311.380 (5)
O7—C351.391 (5)C30—H300.9300
O7—H7A0.849 (19)C31—C321.391 (5)
C1—C181.521 (5)C31—H310.9300
C1—H1A0.9700C32—C331.375 (5)
C1—H1B0.9700C32—H320.9300
C2—C31.495 (4)C33—C341.370 (5)
C2—H2A0.9700C33—H330.9300
C2—H2B0.9700C35—C361.439 (7)
C4—C51.380 (4)C35—H35A0.9700
C4—C91.387 (4)C35—H35B0.9700
C5—C61.377 (4)C36—H36A0.9600
C5—H5A0.9300C36—H36B0.9600
C6—C71.396 (5)C36—H36C0.9600
C6—H60.9300
N2—Zn—N7126.89 (11)C11—C10—H10B109.1
N2—Zn—N993.32 (10)H10A—C10—H10B107.8
N7—Zn—N997.35 (10)N4—C11—N5112.5 (3)
N2—Zn—N488.93 (11)N4—C11—C10124.1 (3)
N7—Zn—N494.27 (10)N5—C11—C10123.4 (3)
N9—Zn—N4163.56 (9)C13—C12—C17119.6 (3)
N2—Zn—N6154.65 (10)C13—C12—N4131.7 (3)
N7—Zn—N678.23 (11)C17—C12—N4108.6 (3)
N9—Zn—N678.38 (10)C14—C13—C12117.9 (3)
N4—Zn—N692.72 (11)C14—C13—H13121.0
N2—Zn—N176.88 (10)C12—C13—H13121.0
N7—Zn—N1154.97 (10)C13—C14—C15122.3 (4)
N9—Zn—N187.86 (10)C13—C14—H14118.9
N4—Zn—N176.79 (10)C15—C14—H14118.9
N6—Zn—N178.90 (10)C16—C15—C14121.2 (4)
C2—N1—C1116.1 (2)C16—C15—H15119.4
C2—N1—C10111.6 (3)C14—C15—H15119.4
C1—N1—C10112.1 (3)C15—C16—C17116.9 (3)
C2—N1—Zn101.61 (18)C15—C16—H16121.5
C1—N1—Zn104.58 (19)C17—C16—H16121.5
C10—N1—Zn109.89 (18)N5—C17—C16132.6 (3)
C3—N2—C4105.7 (3)N5—C17—C12105.3 (3)
C3—N2—Zn114.4 (2)C16—C17—C12122.1 (3)
C4—N2—Zn139.5 (2)N6—C18—C1111.0 (3)
C3—N3—C9108.3 (3)N6—C18—H18A109.4
C3—N3—H3125.9C1—C18—H18A109.4
C9—N3—H3125.9N6—C18—H18B109.4
C11—N4—C12105.7 (3)C1—C18—H18B109.4
C11—N4—Zn114.4 (2)H18A—C18—H18B108.0
C12—N4—Zn134.9 (2)C20—C19—N6108.1 (3)
C11—N5—C17107.9 (3)C20—C19—H19A110.1
C11—N5—H5126.1N6—C19—H19A110.1
C17—N5—H5126.1C20—C19—H19B110.1
C18—N6—C19113.7 (3)N6—C19—H19B110.1
C18—N6—C27112.4 (3)H19A—C19—H19B108.4
C19—N6—C27110.5 (3)N7—C20—N8112.7 (3)
C18—N6—Zn108.2 (2)N7—C20—C19122.3 (3)
C19—N6—Zn102.61 (19)N8—C20—C19124.9 (3)
C27—N6—Zn108.9 (2)C22—C21—C26121.4 (3)
C20—N7—C21105.3 (3)C22—C21—N7130.1 (3)
C20—N7—Zn111.0 (2)C26—C21—N7108.5 (3)
C21—N7—Zn142.5 (2)C23—C22—C21117.2 (3)
C20—N8—C26107.2 (3)C23—C22—H22121.4
C20—N8—H8126.4C21—C22—H22121.4
C26—N8—H8126.4C22—C23—C24121.0 (4)
C28—N9—C29105.0 (3)C22—C23—H23119.5
C28—N9—Zn113.2 (2)C24—C23—H23119.5
C29—N9—Zn141.8 (2)C25—C24—C23122.3 (4)
C28—N10—C34108.0 (3)C25—C24—H24118.9
C28—N10—H10126.0C23—C24—H24118.9
C34—N10—H10126.0C24—C25—C26117.1 (4)
O2—N11—O3121.3 (4)C24—C25—H25121.4
O2—N11—O1119.1 (4)C26—C25—H25121.4
O3—N11—O1119.5 (3)N8—C26—C25132.7 (3)
O5—N12—O4119.1 (4)N8—C26—C21106.3 (3)
O5—N12—O6118.9 (4)C25—C26—C21120.9 (4)
O4—N12—O6122.0 (4)C28—C27—N6111.1 (3)
C35—O7—H7A115 (4)C28—C27—H27A109.4
N1—C1—C18110.3 (3)N6—C27—H27A109.4
N1—C1—H1A109.6C28—C27—H27B109.4
C18—C1—H1A109.6N6—C27—H27B109.4
N1—C1—H1B109.6H27A—C27—H27B108.0
C18—C1—H1B109.6N9—C28—N10112.7 (3)
H1A—C1—H1B108.1N9—C28—C27122.5 (3)
N1—C2—C3108.4 (3)N10—C28—C27124.8 (3)
N1—C2—H2A110.0C30—C29—N9130.7 (3)
C3—C2—H2A110.0C30—C29—C34119.5 (3)
N1—C2—H2B110.0N9—C29—C34109.8 (3)
C3—C2—H2B110.0C29—C30—C31118.0 (3)
H2A—C2—H2B108.4C29—C30—H30121.0
N2—C3—N3112.2 (3)C31—C30—H30121.0
N2—C3—C2121.8 (3)C30—C31—C32121.1 (4)
N3—C3—C2125.9 (3)C30—C31—H31119.5
C5—C4—C9122.0 (3)C32—C31—H31119.5
C5—C4—N2129.5 (3)C33—C32—C31122.0 (4)
C9—C4—N2108.4 (3)C33—C32—H32119.0
C6—C5—C4116.5 (3)C31—C32—H32119.0
C6—C5—H5A121.7C34—C33—C32116.2 (4)
C4—C5—H5A121.7C34—C33—H33121.9
C5—C6—C7121.5 (3)C32—C33—H33121.9
C5—C6—H6119.3C33—C34—N10132.3 (3)
C7—C6—H6119.3C33—C34—C29123.2 (4)
C8—C7—C6122.2 (4)N10—C34—C29104.5 (3)
C8—C7—H7118.9O7—C35—C36111.0 (5)
C6—C7—H7118.9O7—C35—H35A109.4
C7—C8—C9116.6 (3)C36—C35—H35A109.4
C7—C8—H8A121.7O7—C35—H35B109.4
C9—C8—H8A121.7C36—C35—H35B109.4
N3—C9—C4105.4 (3)H35A—C35—H35B108.0
N3—C9—C8133.6 (3)C35—C36—H36A109.5
C4—C9—C8121.1 (3)C35—C36—H36B109.5
N1—C10—C11112.6 (3)H36A—C36—H36B109.5
N1—C10—H10A109.1C35—C36—H36C109.5
C11—C10—H10A109.1H36A—C36—H36C109.5
N1—C10—H10B109.1H36B—C36—H36C109.5
N2—Zn—N1—C234.61 (19)C5—C4—C9—N3176.5 (3)
N7—Zn—N1—C2162.2 (2)N2—C4—C9—N31.1 (3)
N9—Zn—N1—C259.30 (19)C5—C4—C9—C82.2 (5)
N4—Zn—N1—C2126.6 (2)N2—C4—C9—C8179.8 (3)
N6—Zn—N1—C2137.9 (2)C7—C8—C9—N3177.3 (4)
N2—Zn—N1—C1155.8 (2)C7—C8—C9—C41.0 (5)
N7—Zn—N1—C141.0 (3)C2—N1—C10—C11115.1 (3)
N9—Zn—N1—C161.9 (2)C1—N1—C10—C11112.7 (3)
N4—Zn—N1—C1112.2 (2)Zn—N1—C10—C113.1 (3)
N6—Zn—N1—C116.7 (2)C12—N4—C11—N51.1 (4)
N2—Zn—N1—C1083.7 (2)Zn—N4—C11—N5160.0 (2)
N7—Zn—N1—C1079.5 (3)C12—N4—C11—C10176.1 (3)
N9—Zn—N1—C10177.6 (2)Zn—N4—C11—C1017.2 (4)
N4—Zn—N1—C108.3 (2)C17—N5—C11—N41.3 (4)
N6—Zn—N1—C10103.8 (2)C17—N5—C11—C10175.8 (3)
N7—Zn—N2—C3166.2 (2)N1—C10—C11—N49.1 (5)
N9—Zn—N2—C364.4 (2)N1—C10—C11—N5167.7 (3)
N4—Zn—N2—C399.3 (2)C11—N4—C12—C13176.4 (4)
N6—Zn—N2—C35.2 (4)Zn—N4—C12—C1323.9 (6)
N1—Zn—N2—C322.6 (2)C11—N4—C12—C170.4 (4)
N7—Zn—N2—C45.0 (4)Zn—N4—C12—C17152.9 (3)
N9—Zn—N2—C4106.7 (3)C17—C12—C13—C140.1 (5)
N4—Zn—N2—C489.5 (3)N4—C12—C13—C14176.4 (3)
N6—Zn—N2—C4176.3 (3)C12—C13—C14—C150.2 (6)
N1—Zn—N2—C4166.2 (3)C13—C14—C15—C160.6 (7)
N2—Zn—N4—C1163.6 (2)C14—C15—C16—C170.7 (6)
N7—Zn—N4—C11169.5 (2)C11—N5—C17—C16176.3 (4)
N9—Zn—N4—C1134.5 (5)C11—N5—C17—C121.0 (4)
N6—Zn—N4—C1191.1 (2)C15—C16—C17—N5176.5 (4)
N1—Zn—N4—C1113.2 (2)C15—C16—C17—C120.5 (6)
N2—Zn—N4—C1287.1 (3)C13—C12—C17—N5177.6 (3)
N7—Zn—N4—C1239.8 (3)N4—C12—C17—N50.4 (4)
N9—Zn—N4—C12174.7 (3)C13—C12—C17—C160.1 (6)
N6—Zn—N4—C12118.2 (3)N4—C12—C17—C16177.3 (3)
N1—Zn—N4—C12163.9 (3)C19—N6—C18—C1155.1 (3)
N2—Zn—N6—C1830.4 (3)C27—N6—C18—C178.5 (3)
N7—Zn—N6—C18156.6 (2)Zn—N6—C18—C141.8 (3)
N9—Zn—N6—C18103.2 (2)N1—C1—C18—N660.9 (4)
N4—Zn—N6—C1862.8 (2)C18—N6—C19—C20156.5 (3)
N1—Zn—N6—C1813.2 (2)C27—N6—C19—C2076.0 (3)
N2—Zn—N6—C19150.9 (2)Zn—N6—C19—C2039.9 (3)
N7—Zn—N6—C1936.1 (2)C21—N7—C20—N80.7 (4)
N9—Zn—N6—C19136.3 (2)Zn—N7—C20—N8169.7 (2)
N4—Zn—N6—C1957.7 (2)C21—N7—C20—C19179.5 (3)
N1—Zn—N6—C19133.6 (2)Zn—N7—C20—C199.1 (4)
N2—Zn—N6—C2792.0 (3)C26—N8—C20—N70.5 (4)
N7—Zn—N6—C2781.0 (2)C26—N8—C20—C19178.3 (3)
N9—Zn—N6—C2719.20 (19)N6—C19—C20—N724.0 (4)
N4—Zn—N6—C27174.8 (2)N6—C19—C20—N8157.3 (3)
N1—Zn—N6—C27109.3 (2)C20—N7—C21—C22178.2 (3)
N2—Zn—N7—C20158.5 (2)Zn—N7—C21—C2216.6 (6)
N9—Zn—N7—C20101.7 (2)C20—N7—C21—C261.6 (3)
N4—Zn—N7—C2066.6 (2)Zn—N7—C21—C26163.5 (3)
N6—Zn—N7—C2025.3 (2)C26—C21—C22—C230.5 (5)
N1—Zn—N7—C200.9 (4)N7—C21—C22—C23179.6 (3)
N2—Zn—N7—C216.2 (4)C21—C22—C23—C240.7 (5)
N9—Zn—N7—C2193.6 (3)C22—C23—C24—C251.0 (6)
N4—Zn—N7—C2198.0 (3)C23—C24—C25—C260.1 (6)
N6—Zn—N7—C21170.1 (4)C20—N8—C26—C25179.0 (4)
N1—Zn—N7—C21165.6 (3)C20—N8—C26—C211.5 (4)
N2—Zn—N9—C28164.5 (2)C24—C25—C26—N8178.1 (4)
N7—Zn—N9—C2867.7 (2)C24—C25—C26—C211.4 (5)
N4—Zn—N9—C2867.0 (5)C22—C21—C26—N8178.0 (3)
N6—Zn—N9—C288.7 (2)N7—C21—C26—N81.9 (3)
N1—Zn—N9—C2887.8 (2)C22—C21—C26—C251.6 (5)
N2—Zn—N9—C2911.5 (3)N7—C21—C26—C25178.5 (3)
N7—Zn—N9—C29116.3 (3)C18—N6—C27—C2893.6 (3)
N4—Zn—N9—C29109.0 (5)C19—N6—C27—C28138.2 (3)
N6—Zn—N9—C29167.4 (3)Zn—N6—C27—C2826.2 (3)
N1—Zn—N9—C2988.2 (3)C29—N9—C28—N100.2 (3)
C2—N1—C1—C18155.0 (3)Zn—N9—C28—N10177.3 (2)
C10—N1—C1—C1875.0 (3)C29—N9—C28—C27178.1 (3)
Zn—N1—C1—C1844.0 (3)Zn—N9—C28—C274.4 (4)
C1—N1—C2—C3152.3 (3)C34—N10—C28—N90.0 (4)
C10—N1—C2—C377.5 (3)C34—N10—C28—C27178.2 (3)
Zn—N1—C2—C339.6 (3)N6—C27—C28—N921.8 (4)
C4—N2—C3—N31.4 (4)N6—C27—C28—N10160.1 (3)
Zn—N2—C3—N3172.7 (2)C28—N9—C29—C30179.9 (3)
C4—N2—C3—C2180.0 (3)Zn—N9—C29—C303.9 (6)
Zn—N2—C3—C25.9 (4)C28—N9—C29—C340.2 (3)
C9—N3—C3—N20.7 (4)Zn—N9—C29—C34176.0 (2)
C9—N3—C3—C2179.2 (3)N9—C29—C30—C31179.3 (3)
N1—C2—C3—N227.5 (4)C34—C29—C30—C310.8 (5)
N1—C2—C3—N3154.2 (3)C29—C30—C31—C320.9 (5)
C3—N2—C4—C5175.8 (3)C30—C31—C32—C330.2 (6)
Zn—N2—C4—C512.6 (6)C31—C32—C33—C340.5 (6)
C3—N2—C4—C91.5 (3)C32—C33—C34—N10179.1 (3)
Zn—N2—C4—C9170.1 (2)C32—C33—C34—C290.5 (5)
C9—C4—C5—C61.8 (5)C28—N10—C34—C33179.8 (4)
N2—C4—C5—C6178.8 (3)C28—N10—C34—C290.1 (3)
C4—C5—C6—C70.2 (5)C30—C29—C34—C330.2 (5)
C5—C6—C7—C81.0 (6)N9—C29—C34—C33179.9 (3)
C6—C7—C8—C90.6 (5)C30—C29—C34—N10179.9 (3)
C3—N3—C9—C40.3 (4)N9—C29—C34—N100.2 (3)
C3—N3—C9—C8178.8 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3···O1i0.862.002.787 (4)152
N3—H3···O2i0.862.353.037 (4)137
N5—H5···O50.862.052.875 (4)160
N8—H8···O7ii0.861.912.762 (4)169
N10—H10···O5iii0.862.282.988 (4)140
O7—H7A···O4iv0.85 (2)2.26 (3)3.039 (5)152 (5)
O7—H7A···O6iv0.85 (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
Mr816.15
Crystal system, space groupTriclinic, 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)
V3)1838.9 (11)
Z2
Radiation typeMo Kα
µ (mm1)0.74
Crystal size (mm)0.50 × 0.36 × 0.36
Data collection
DiffractometerSiemens P4
diffractometer
Absorption correctionEmpirical (using intensity measurements)
via ψ scan (North et al., 1968)
Tmin, Tmax0.735, 0.768
No. of measured, independent and
observed [I > 2σ(I)] reflections
7751, 6479, 3961
Rint0.022
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.089, 0.85
No. of reflections6479
No. of parameters509
No. of restraints2
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.26, 0.30

Computer programs: XSCANS (Siemens, 1994), XSCANS, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL-Plus (Sheldrick, 1990).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3···O1i0.862.002.787 (4)152
N3—H3···O2i0.862.353.037 (4)137
N5—H5···O50.862.052.875 (4)160
N8—H8···O7ii0.861.912.762 (4)169
N10—H10···O5iii0.862.282.988 (4)140
O7—H7A···O4iv0.849 (19)2.26 (3)3.039 (5)152 (5)
O7—H7A···O6iv0.849 (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.
 

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