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The centrosymmetric dinuclear title compound, [Zn2(C17H17N2O)4]·2C17H18N2O, has one 2-(1-butyl­benzimidazol-2-yl)phenolate acting as a chelating ligand and the other as a bridging ligand, conferring a tetra­hedral geometry on the Zn atom. The uncoordinated 2-(1-butyl­benzimidazol-2-yl)phenol mol­ecule inter­acts with the O atom of the chelating anion through a hydrogen bond.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805027418/bt6722sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805027418/bt6722Isup2.hkl
Contains datablock I

CCDC reference: 287462

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.005 Å
  • Disorder in main residue
  • R factor = 0.068
  • wR factor = 0.196
  • Data-to-parameter ratio = 13.8

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT220_ALERT_2_A Large Non-Solvent C Ueq(max)/Ueq(min) ... 5.38 Ratio
Author Response: Disorder
PLAT222_ALERT_3_A Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       5.14 Ratio
Author Response: Disorder
PLAT432_ALERT_2_A Short Inter X...Y Contact  C11    ..  C28'    ..       2.86 Ang.
Author Response: Disorder

Alert level B ABSTM02_ALERT_3_B The ratio of expected to reported Tmax/Tmin(RR') is < 0.75 Tmin and Tmax reported: 0.448 0.976 Tmin(prime) and Tmax expected: 0.878 0.976 RR(prime) = 0.510 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large ............. 0.51 PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.71 Ratio
Author Response: Disorder
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.27 Ratio
Author Response: Disorder

Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT301_ALERT_3_C Main Residue Disorder ......................... 13.00 Perc. PLAT722_ALERT_1_C Angle Calc 111.00, Rep 109.90 Dev... 1.10 Deg. C26 -C27 -H27A 1.555 1.555 1.555
3 ALERT level A = In general: serious problem 4 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 5 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

Following a report on the exceptional electroluminescence of the dimeric zinc derivative of benzthiazol-2-ylphen-2-ol (Yu et al., 2003), we have been able to synthesize the benzthiazol-2-ylphenol-2-ate/benzoxazol-2-ylphenol-2-ate, which is a mixed dinuclear compound (Tong et al., 2004), the 5-aminobenzimidazol-2-ylphen-2-olate, which exists as a co-crystal with zinc bis(benzimidazol-2-yl-phen-2-olate) (Tong, 2005a), and the benzimidazol-2-yl-(4-bromophen-4-olate) (Tong, 2005b). The second and third are monomeric compounds that also exhibit luminescence. The title zinc derivative, (I), of 1-butylbenzimidazol-2-ylphen-2-ol exists as a centrosymmetric dimer, the dimer crystallizing with two molecules of the ligand (Fig. 1). One 1-butylbenzimidazol-2-ylphen-2-olate functions in an O,N-chelating mode [Zn–O = 1.963 (3) Å] and the other in an O,N-bridging mode [Zn–O = 1.904 (3) Å]; the longer zinc–oxygen bond length for the chelating anion suggests that chelation is probably sterically unfavorable. The Zn atom is four-coordinate in a tetrahedral geometry. The dinuclear molecule interacts with the uncoordinated heterocycle through a hydrogen bond [O···O = 2.660 (4) Å].

Experimental top

1-Butyl-1H-benzimidazol-2-yl-phen-2-ol was synthesized using the procedure for synthesizing 1-ethyl-1H-benzimidazol-2-ylphen-2-ol (Addison & Burke, 1981). Salicylic acid and o-phenylenediamine in syrupy phosphoric acid were heated at 520 K for 5 h; the product (in 10% yield) was then reacted with 1-bromobutane to form the desired heterocyclic compound in 70% yield. Zinc acetate dihydrate (0.022 g, 0.1 mmol), the heterocycle (0.064 g, 0.2 mmol), potassium hydroxide (0.020 g, 0.4 mmol) and water (10 ml) were heated in a 23 ml Teflon-lined Parr bomb at 368 K for 4 d. The bomb was cooled to room temperature at 5 K h−1. Analysis found: C 71.14, H 6.21, N 9.62%; calculated for C102H104N12O6Zn2: C 71.03, H 6.08, N 9.75%.

Refinement top

The 2-, 3- and 4-carbon atoms of the three butyl groups are disordered over two positions; the occupancies refined to 0.53 (1):0.47 (1), 0.68 (1):0.32 (1) and 0.53 (1):0.47 (1). The occupancies for two of the three was set to equal each other so avoid any short interaction between the unprimed butyl group of the lattice ligand and the primed butyl group of the coordinated ligand. The C–C distances were restrained to 1.540±0.005 and the 1,3-related distances to 2.51±0.01 Å. The vibrations of the disordered carbon atoms were restrained to be nearly isotropic; additionally, the temperature factors of the disordered atoms along the butyl chains were restrained to increase only gradually.

The phenyl and o-phenylene rings were refined as rigid hexagons of 1.39 Å sides so as to increase the reflections-to-variables ratio; refining their atoms freely did not significantly lower the R index.

Hydrogen atoms were placed at calculated positions in the riding model approximation (C–Haromatic = 0.93 Å, C–Hmethylene = 0.97 Å and C–Hmethyl = 0.96 Å) with their temperature factors tied to those of the parent atoms by U(H) = 1.2 to 1.5Ueq (C). The hydroxy group was rotated to fit the electron density [O–H = 0.82 Å, U(H) = 1.5Ueq(O)].

The unprimed butyl component of the chelating anion is 2.67 Å from the primed butyl component of the free ligand.

Computing details top

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. ORTEP (Johnson, 1976) plot of (I), with displacement ellipsoids drawn at the 30% probability level. Only the major disorder component is shown; the uncoordinated heterocycle is not shown. H atoms are drawn as spheres of arbitrary radii. [Symmetry code (i): 1 − x, 1 − y, 1 − z.]
Bis[µ-2-(1-butylbenzimidazol-2-yl)phenolato]-κ2N3,O';κ2N3',O- bis{[2-(1-butylbenzimidazol-2-yl)phenolato-κ2N3,O]zinc(II)} 2-(1-butylbenzimidazol-2-yl)phenol disolvate top
Crystal data top
[Zn2(C17H17N2O)4]·2C17H18N2OZ = 1
Mr = 1724.71F(000) = 908
Triclinic, P1Dx = 1.296 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.750 (1) ÅCell parameters from 1973 reflections
b = 11.839 (1) Åθ = 2.2–19.6°
c = 18.709 (2) ŵ = 0.61 mm1
α = 93.070 (2)°T = 295 K
β = 105.927 (1)°Plate, colorless
γ = 103.382 (2)°0.21 × 0.15 × 0.04 mm
V = 2210.0 (3) Å3
Data collection top
Bruker APEX area-detector
diffractometer
7679 independent reflections
Radiation source: fine-focus sealed tube5409 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
ϕ and ω scanθmax = 25.0°, θmin = 1.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1212
Tmin = 0.448, Tmax = 0.976k = 1413
11754 measured reflectionsl = 2220
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)] = 0.068Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.196H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.1132P)2 + 0.1952P]
where P = (Fo2 + 2Fc2)/3
7679 reflections(Δ/σ)max = 0.001
556 parametersΔρmax = 0.52 e Å3
192 restraintsΔρmin = 0.36 e Å3
Crystal data top
[Zn2(C17H17N2O)4]·2C17H18N2Oγ = 103.382 (2)°
Mr = 1724.71V = 2210.0 (3) Å3
Triclinic, P1Z = 1
a = 10.750 (1) ÅMo Kα radiation
b = 11.839 (1) ŵ = 0.61 mm1
c = 18.709 (2) ÅT = 295 K
α = 93.070 (2)°0.21 × 0.15 × 0.04 mm
β = 105.927 (1)°
Data collection top
Bruker APEX area-detector
diffractometer
7679 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
5409 reflections with I > 2σ(I)
Tmin = 0.448, Tmax = 0.976Rint = 0.028
11754 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.068192 restraints
wR(F2) = 0.196H-atom parameters constrained
S = 1.02Δρmax = 0.52 e Å3
7679 reflectionsΔρmin = 0.36 e Å3
556 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Zn10.69644 (5)0.70785 (4)0.55340 (3)0.0418 (2)
O10.7406 (3)0.8693 (2)0.6018 (2)0.045 (1)
O20.5744 (3)0.6050 (3)0.5926 (2)0.048 (1)
O30.7220 (4)0.9044 (3)0.7397 (2)0.061 (1)
N10.8772 (3)0.6890 (3)0.6046 (2)0.044 (1)
N21.0742 (4)0.7532 (4)0.6909 (2)0.057 (1)
N30.3755 (3)0.3031 (3)0.5570 (2)0.040 (1)
N40.4792 (4)0.3909 (3)0.6725 (2)0.048 (1)
N50.7649 (5)1.0366 (4)0.9307 (3)0.073 (1)
N60.8909 (5)1.1168 (4)0.8609 (2)0.065 (1)
C10.8604 (2)0.9408 (2)0.6051 (2)0.045 (1)
C20.8642 (3)1.0558 (2)0.5917 (2)0.057 (1)
C30.9840 (4)1.1319 (2)0.5918 (2)0.078 (2)
C41.0999 (3)1.0932 (3)0.6053 (2)0.084 (2)
C51.0961 (2)0.9783 (3)0.6187 (2)0.072 (2)
C60.9763 (3)0.9021 (2)0.6186 (2)0.050 (1)
C70.9759 (4)0.7827 (4)0.6374 (3)0.050 (1)
C81.1850 (4)0.8313 (6)0.7518 (3)0.081 (2)
C91.3221 (7)0.830 (1)0.7426 (5)0.092 (4)0.53 (1)
C101.431 (1)0.918 (1)0.8052 (6)0.120 (5)0.53 (1)
C111.4355 (6)0.872 (1)0.8813 (4)0.162 (7)0.53 (1)
C9'1.3211 (6)0.830 (1)0.7408 (4)0.105 (5)0.47 (1)
C10'1.430 (1)0.865 (2)0.8171 (8)0.140 (6)0.47 (1)
C11'1.425 (2)0.985 (2)0.8522 (11)0.196 (9)0.47 (1)
C121.0350 (3)0.6356 (2)0.6917 (2)0.056 (1)
C131.0914 (3)0.5574 (3)0.7343 (2)0.074 (2)
C141.0223 (4)0.4402 (3)0.7245 (2)0.082 (2)
C150.8968 (4)0.4011 (2)0.6720 (2)0.078 (2)
C160.8404 (3)0.4792 (3)0.6294 (2)0.058 (1)
C170.9095 (3)0.5965 (2)0.6392 (2)0.047 (1)
C180.4445 (2)0.6056 (2)0.5782 (2)0.042 (1)
C190.4003 (3)0.7044 (2)0.5589 (2)0.052 (1)
C200.2659 (3)0.7017 (2)0.5456 (2)0.059 (1)
C210.1756 (2)0.6001 (3)0.5515 (2)0.058 (1)
C220.2198 (2)0.5013 (2)0.5708 (2)0.053 (1)
C230.3543 (3)0.5041 (2)0.5841 (2)0.041 (1)
C240.4017 (4)0.3997 (4)0.6039 (2)0.039 (1)
C250.5261 (6)0.4783 (5)0.7369 (3)0.071 (2)
C260.433 (1)0.452 (1)0.7867 (6)0.095 (3)0.68 (1)
C270.484 (1)0.551 (1)0.8524 (6)0.134 (5)0.68 (1)
C26'0.460 (3)0.459 (2)0.800 (1)0.104 (6)0.32 (1)
C280.405 (2)0.520 (2)0.9089 (7)0.200 (8)0.68 (1)
C27'0.550 (3)0.539 (3)0.8720 (7)0.142 (8)0.32 (1)
C28'0.504 (4)0.653 (2)0.876 (2)0.213 (13)0.32 (1)
C290.5063 (3)0.2844 (2)0.6703 (2)0.049 (1)
C300.5811 (3)0.2283 (3)0.7227 (1)0.066 (2)
C310.5905 (3)0.1165 (3)0.7026 (2)0.073 (2)
C320.5251 (3)0.0608 (2)0.6302 (2)0.068 (2)
C330.4503 (3)0.1169 (2)0.5778 (1)0.058 (1)
C340.4409 (3)0.2287 (2)0.5979 (1)0.043 (1)
C350.7922 (3)0.8469 (3)0.7902 (2)0.050 (1)
C360.8063 (3)0.7364 (3)0.7711 (1)0.055 (1)
C370.8760 (4)0.6798 (2)0.8255 (2)0.067 (2)
C380.9316 (4)0.7337 (3)0.8990 (2)0.079 (2)
C390.9175 (4)0.8442 (3)0.9181 (1)0.075 (2)
C400.8479 (3)0.9007 (2)0.8637 (2)0.056 (1)
C410.8324 (5)1.0176 (4)0.8851 (3)0.059 (1)
C420.9734 (6)1.1286 (6)0.8107 (4)0.094 (2)
C431.1220 (8)1.190 (1)0.8427 (9)0.119 (4)0.53 (1)
C441.1929 (9)1.118 (1)0.8977 (9)0.144 (5)0.53 (1)
C451.3452 (7)1.164 (1)0.9104 (7)0.188 (8)0.53 (1)
C43'1.1172 (7)1.128 (1)0.8533 (7)0.116 (5)0.47 (1)
C44'1.184 (1)1.239 (1)0.909 (1)0.151 (6)0.47 (1)
C45'1.326 (1)1.236 (2)0.954 (1)0.178 (9)0.47 (1)
C460.8589 (4)1.2070 (3)0.8927 (2)0.069 (2)
C470.8865 (4)1.3272 (4)0.8902 (2)0.093 (2)
C480.8345 (5)1.3962 (3)0.9307 (3)0.111 (3)
C490.7549 (5)1.3452 (4)0.9736 (3)0.114 (3)
C500.7273 (4)1.2251 (4)0.9761 (2)0.103 (2)
C510.7793 (4)1.1560 (3)0.9356 (2)0.073 (2)
H3o0.73390.89160.69880.091*
H20.78661.08170.58270.069*
H30.98651.20880.58280.094*
H41.18001.14420.60540.100*
H51.17370.95240.62770.086*
H8a1.18020.80640.79970.097*
H8b1.17480.91060.75150.097*
H9a1.32670.85170.69400.111*0.53 (1)
H9b1.33560.75190.74590.111*0.53 (1)
H10a1.41170.99340.80570.144*0.53 (1)
H10b1.51760.92630.79630.144*0.53 (1)
H11a1.50610.92370.92040.243*0.53 (1)
H11b1.45140.79510.87990.243*0.53 (1)
H11c1.35140.86720.89110.243*0.53 (1)
H9c1.34160.88450.70620.126*0.47 (1)
H9d1.31830.75240.72000.126*0.47 (1)
H10c1.51730.87090.81040.168*0.47 (1)
H10d1.41460.80630.85010.168*0.47 (1)
H11d1.50041.01290.89580.294*0.47 (1)
H11e1.34370.97540.86610.294*0.47 (1)
H11f1.42671.03960.81640.294*0.47 (1)
H131.17530.58360.76940.089*
H141.06000.38790.75300.098*
H150.85060.32270.66550.094*
H160.75650.45310.59430.070*
H190.46070.77230.55490.062*
H200.23630.76780.53270.071*
H210.08570.59830.54260.069*
H220.15950.43340.57480.063*
H25a0.52750.55510.72080.085*
H25b0.61660.47850.76510.085*
H26a0.43530.37730.80540.113*0.68 (1)
H26b0.34180.44820.75820.113*0.68 (1)
H27a0.57830.56170.87650.161*0.68 (1)
H27b0.47060.62420.83400.161*0.68 (1)
H28a0.43610.58170.95000.300*0.68 (1)
H28b0.41880.44840.92710.300*0.68 (1)
H28c0.31160.51090.88480.300*0.68 (1)
H26c0.44770.37760.80940.124*0.32 (1)
H26d0.37320.47530.78520.124*0.32 (1)
H27c0.54330.50040.91560.170*0.32 (1)
H27d0.64250.55760.87180.170*0.32 (1)
H28d0.54370.69490.92510.319*0.32 (1)
H28e0.40840.63430.86390.319*0.32 (1)
H28f0.53170.70090.84010.319*0.32 (1)
H300.62490.26560.77110.079*
H310.64060.07900.73760.088*
H320.53140.01400.61680.082*
H330.40650.07970.52940.069*
H360.76910.70030.72200.066*
H370.88540.60590.81270.081*
H380.97820.69580.93540.095*
H390.95470.88020.96720.089*
H42a0.93511.17020.77060.112*
H42b0.96621.05070.78820.112*
H43a1.13251.26680.86830.143*0.53 (1)
H43b1.16241.20090.80230.143*0.53 (1)
H44a1.16351.03550.87720.173*0.53 (1)
H44b1.17221.12510.94480.173*0.53 (1)
H45a1.39321.13480.95360.282*0.53 (1)
H45b1.36921.24800.91830.282*0.53 (1)
H45c1.36771.13810.86720.282*0.53 (1)
H43c1.11621.05950.87990.139*0.47 (1)
H43d1.16811.12340.81810.139*0.47 (1)
H44c1.13111.24510.94320.181*0.47 (1)
H44d1.18781.30740.88250.181*0.47 (1)
H45d1.34491.26831.00470.268*0.47 (1)
H45e1.38951.28000.93180.268*0.47 (1)
H45f1.33201.15580.95220.268*0.47 (1)
H470.93981.36130.86150.112*
H480.85301.47660.92900.133*
H490.72011.39141.00070.137*
H500.67411.19091.00480.124*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.0357 (3)0.0393 (3)0.0453 (3)0.0053 (2)0.0070 (2)0.0051 (2)
O10.040 (2)0.038 (2)0.053 (2)0.004 (1)0.013 (1)0.004 (1)
O20.034 (2)0.047 (2)0.062 (2)0.008 (1)0.011 (1)0.018 (2)
O30.072 (2)0.071 (2)0.043 (2)0.035 (2)0.009 (2)0.007 (2)
N10.038 (2)0.041 (2)0.051 (2)0.009 (2)0.010 (2)0.006 (2)
N20.039 (2)0.057 (3)0.063 (3)0.010 (2)0.001 (2)0.005 (2)
N30.036 (2)0.036 (2)0.043 (2)0.007 (2)0.008 (2)0.006 (2)
N40.050 (2)0.040 (2)0.045 (2)0.006 (2)0.002 (2)0.006 (2)
N50.082 (3)0.066 (3)0.068 (3)0.016 (3)0.020 (3)0.001 (2)
N60.083 (3)0.050 (3)0.055 (3)0.013 (2)0.011 (2)0.001 (2)
C10.042 (2)0.042 (3)0.047 (3)0.008 (2)0.011 (2)0.002 (2)
C20.054 (3)0.044 (3)0.074 (4)0.009 (2)0.021 (3)0.012 (3)
C30.081 (4)0.047 (3)0.106 (5)0.005 (3)0.035 (4)0.012 (3)
C40.060 (4)0.056 (4)0.129 (6)0.007 (3)0.037 (4)0.017 (4)
C50.042 (3)0.070 (4)0.102 (5)0.006 (3)0.023 (3)0.012 (3)
C60.044 (3)0.044 (3)0.058 (3)0.002 (2)0.015 (2)0.006 (2)
C70.037 (2)0.056 (3)0.054 (3)0.012 (2)0.011 (2)0.008 (2)
C80.051 (3)0.090 (4)0.085 (4)0.008 (3)0.000 (3)0.006 (3)
C90.072 (6)0.105 (6)0.090 (6)0.011 (5)0.017 (5)0.011 (5)
C100.110 (7)0.128 (8)0.109 (7)0.014 (6)0.026 (6)0.015 (6)
C110.16 (1)0.17 (1)0.14 (1)0.014 (8)0.042 (8)0.032 (8)
C9'0.047 (7)0.127 (8)0.112 (8)0.000 (7)0.003 (7)0.000 (8)
C10'0.081 (9)0.16 (1)0.14 (1)0.002 (9)0.007 (8)0.01 (1)
C11'0.14 (1)0.20 (2)0.21 (2)0.02 (1)0.02 (1)0.07 (2)
C120.046 (3)0.067 (4)0.058 (3)0.024 (3)0.013 (2)0.011 (3)
C130.054 (3)0.091 (5)0.080 (4)0.034 (3)0.009 (3)0.022 (3)
C140.084 (4)0.084 (5)0.093 (5)0.047 (4)0.024 (4)0.038 (4)
C150.091 (5)0.058 (4)0.097 (5)0.026 (3)0.036 (4)0.025 (3)
C160.064 (3)0.052 (3)0.066 (3)0.023 (3)0.023 (3)0.012 (3)
C170.043 (3)0.051 (3)0.053 (3)0.018 (2)0.018 (2)0.008 (2)
C180.043 (2)0.039 (2)0.041 (2)0.009 (2)0.011 (2)0.005 (2)
C190.050 (3)0.041 (3)0.061 (3)0.008 (2)0.013 (2)0.007 (2)
C200.060 (3)0.055 (3)0.071 (4)0.029 (3)0.019 (3)0.014 (3)
C210.043 (3)0.069 (4)0.066 (3)0.025 (3)0.015 (2)0.011 (3)
C220.044 (3)0.052 (3)0.061 (3)0.005 (2)0.018 (2)0.007 (2)
C230.037 (2)0.038 (2)0.046 (3)0.005 (2)0.013 (2)0.006 (2)
C240.031 (2)0.042 (3)0.041 (3)0.004 (2)0.009 (2)0.008 (2)
C250.085 (4)0.068 (3)0.050 (3)0.025 (3)0.001 (3)0.003 (3)
C260.109 (6)0.103 (5)0.069 (5)0.037 (5)0.017 (5)0.003 (4)
C270.144 (7)0.141 (7)0.117 (7)0.052 (6)0.028 (6)0.004 (6)
C280.21 (1)0.22 (1)0.18 (1)0.056 (8)0.065 (8)0.004 (8)
C26'0.12 (1)0.099 (9)0.074 (9)0.029 (9)0.006 (8)0.021 (8)
C27'0.15 (1)0.14 (1)0.12 (1)0.04 (1)0.01 (1)0.02 (1)
C28'0.21 (2)0.18 (2)0.18 (2)0.01 (2)0.006 (19)0.075 (18)
C290.043 (3)0.045 (3)0.051 (3)0.007 (2)0.007 (2)0.014 (2)
C300.066 (3)0.065 (4)0.054 (3)0.021 (3)0.006 (3)0.014 (3)
C310.072 (4)0.064 (4)0.081 (4)0.029 (3)0.006 (3)0.022 (3)
C320.070 (4)0.052 (3)0.084 (4)0.026 (3)0.015 (3)0.011 (3)
C330.062 (3)0.047 (3)0.059 (3)0.016 (2)0.009 (3)0.005 (2)
C340.039 (2)0.039 (3)0.052 (3)0.009 (2)0.015 (2)0.013 (2)
C350.048 (3)0.053 (3)0.051 (3)0.014 (2)0.014 (2)0.012 (2)
C360.064 (3)0.057 (3)0.045 (3)0.018 (3)0.016 (2)0.003 (2)
C370.073 (4)0.058 (3)0.071 (4)0.024 (3)0.014 (3)0.015 (3)
C380.087 (4)0.068 (4)0.068 (4)0.024 (3)0.006 (3)0.018 (3)
C390.093 (4)0.059 (4)0.051 (3)0.015 (3)0.008 (3)0.005 (3)
C400.060 (3)0.053 (3)0.048 (3)0.009 (2)0.007 (2)0.007 (2)
C410.062 (3)0.053 (3)0.047 (3)0.009 (3)0.000 (3)0.003 (2)
C420.108 (5)0.077 (4)0.098 (5)0.014 (4)0.042 (4)0.012 (4)
C430.123 (6)0.106 (7)0.123 (7)0.022 (5)0.035 (6)0.010 (6)
C440.137 (8)0.136 (8)0.144 (8)0.023 (6)0.028 (6)0.013 (7)
C450.17 (1)0.18 (1)0.20 (1)0.046 (8)0.038 (8)0.013 (8)
C43'0.113 (8)0.104 (8)0.123 (9)0.010 (7)0.039 (7)0.014 (7)
C44'0.13 (1)0.15 (1)0.14 (1)0.01 (1)0.022 (9)0.009 (9)
C45'0.12 (1)0.20 (2)0.18 (2)0.01 (1)0.02 (1)0.00 (2)
C460.075 (4)0.061 (4)0.056 (3)0.012 (3)0.001 (3)0.007 (3)
C470.110 (5)0.063 (4)0.087 (5)0.025 (4)0.004 (4)0.003 (3)
C480.124 (7)0.073 (5)0.110 (6)0.039 (5)0.014 (5)0.008 (4)
C490.109 (6)0.085 (6)0.134 (7)0.049 (5)0.000 (5)0.026 (5)
C500.104 (5)0.093 (6)0.113 (6)0.036 (5)0.031 (5)0.010 (4)
C510.070 (4)0.072 (4)0.066 (4)0.026 (3)0.000 (3)0.016 (3)
Geometric parameters (Å, º) top
Zn1—O11.963 (3)C48—C491.39
Zn1—O21.904 (3)C49—C501.39
Zn1—N11.987 (3)C50—C511.39
Zn1—N3i1.981 (3)O3—H3o0.82
O1—C11.351 (3)C2—H20.93
O2—C181.349 (3)C3—H30.93
O3—C351.357 (4)C4—H40.93
N1—C71.327 (5)C5—H50.93
N1—C171.367 (4)C8—H8a0.97
N2—C121.361 (5)C8—H8b0.97
N2—C71.366 (6)C9—H9a0.97
N2—C81.484 (6)C9—H9b0.97
N3—C241.329 (5)C10—H10a0.97
N3—C341.386 (4)C10—H10b0.97
N3—Zn1i1.981 (3)C11—H11a0.96
N4—C241.349 (5)C11—H11b0.96
N4—C291.359 (4)C11—H11c0.96
N4—C251.438 (6)C9'—H9c0.97
N5—C411.303 (7)C9'—H9d0.97
N5—C511.381 (5)C10'—H10c0.97
N6—C461.352 (5)C10'—H10d0.97
N6—C411.361 (7)C11'—H11d0.96
N6—C421.450 (8)C11'—H11e0.96
C1—C21.3900C11'—H11f0.96
C1—C61.3900C13—H130.93
C2—C31.3900C14—H140.93
C3—C41.3900C15—H150.93
C4—C51.3900C16—H160.93
C5—C61.3900C19—H190.93
C6—C71.474 (5)C20—H200.93
C8—C91.534 (5)C21—H210.93
C8—C9'1.535 (5)C22—H220.93
C9—C101.542 (5)C25—H25a0.97
C10—C111.544 (5)C25—H25b0.97
C9'—C10'1.540 (5)C26—H26a0.97
C10'—C11'1.545 (5)C26—H26b0.97
C12—C131.3900C27—H27a0.97
C12—C171.3900C27—H27b0.97
C13—C141.3900C28—H28a0.96
C14—C151.3900C28—H28b0.96
C15—C161.3900C28—H28c0.96
C16—C171.3900C26'—H26c0.97
C18—C191.3900C26'—H26d0.97
C18—C231.3900C27'—H27c0.97
C19—C201.3900C27'—H27d0.97
C20—C211.3900C28'—H28d0.96
C21—C221.3900C28'—H28e0.96
C22—C231.3900C28'—H28f0.96
C23—C241.470 (5)C30—H300.93
C25—C261.538 (5)C31—H310.93
C25—C26'1.538 (5)C32—H320.93
C26—C271.542 (5)C33—H330.93
C27—C281.532 (5)C36—H360.93
C26'—C27'1.542 (5)C37—H370.93
C27'—C28'1.540 (5)C38—H380.93
C29—C301.3900C39—H390.93
C29—C341.3900C42—H42a0.97
C30—C311.3900C42—H42b0.97
C31—C321.3900C43—H43a0.97
C32—C331.3900C43—H43b0.97
C33—C341.3900C44—H44a0.97
C35—C361.3900C44—H44b0.97
C35—C401.3900C45—H45a0.96
C36—C371.3900C45—H45b0.96
C37—C381.3900C45—H45c0.96
C38—C391.3900C43'—H43c0.97
C39—C401.3900C43'—H43d0.97
C40—C411.478 (6)C44'—H44c0.97
C42—C431.527 (5)C44'—H44d0.97
C42—C43'1.536 (5)C45'—H45d0.96
C43—C441.533 (5)C45'—H45e0.96
C44—C451.548 (5)C45'—H45f0.96
C43'—C44'1.533 (5)C47—H470.93
C44'—C45'1.540 (5)C48—H480.93
C46—C471.39C49—H490.93
C46—C511.39C50—H500.93
C47—C481.39
O1—Zn1—O2111.3 (1)H11a—C11—H11b109.5
O1—Zn1—N192.5 (1)C10—C11—H11c109.5
O1—Zn1—N3i111.9 (1)H11a—C11—H11c109.5
O2—Zn1—N1106.4 (1)H11b—C11—H11c109.5
O2—Zn1—N3i110.4 (1)C8—C9'—H9c109.9
N1—Zn1—N3i123.1 (2)C10'—C9'—H9c109.9
C1—O1—Zn1118.1 (2)C8—C9'—H9d109.9
C18—O2—Zn1123.0 (2)C10'—C9'—H9d109.9
C7—N1—C17106.6 (3)H9c—C9'—H9d108.3
C7—N1—Zn1119.6 (3)C9'—C10'—H10c109.9
C17—N1—Zn1128.2 (3)C11'—C10'—H10c109.9
C12—N2—C7107.2 (4)C9'—C10'—H10d109.9
C12—N2—C8122.6 (4)C11'—C10'—H10d109.9
C7—N2—C8128.4 (4)H10c—C10'—H10d108.3
C24—N3—C34105.7 (3)C10'—C11'—H11d109.5
C24—N3—Zn1i124.4 (3)C10'—C11'—H11e109.5
C34—N3—Zn1i127.7 (3)H11d—C11'—H11e109.5
C24—N4—C29108.0 (3)C10'—C11'—H11f109.5
C24—N4—C25126.5 (4)H11d—C11'—H11f109.5
C29—N4—C25125.5 (4)H11e—C11'—H11f109.5
C41—N5—C51103.9 (4)C12—C13—H13120.0
C46—N6—C41107.4 (5)C14—C13—H13120.0
C46—N6—C42124.4 (5)C15—C14—H14120.0
C41—N6—C42128.2 (5)C13—C14—H14120.0
O1—C1—C2117.6 (2)C14—C15—H15120.0
O1—C1—C6122.3 (2)C16—C15—H15120.0
C2—C1—C6120.0C17—C16—H16120.0
C1—C2—C3120.0C15—C16—H16120.0
C4—C3—C2120.0C18—C19—H19120.0
C3—C4—C5120.0C20—C19—H19120.0
C6—C5—C4120.0C21—C20—H20120.0
C5—C6—C1120.0C19—C20—H20120.0
C5—C6—C7119.2 (3)C20—C21—H21120.0
C1—C6—C7120.7 (3)C22—C21—H21120.0
N1—C7—N2110.8 (4)C23—C22—H22120.0
N1—C7—C6123.7 (4)C21—C22—H22120.0
N2—C7—C6125.4 (4)N4—C25—H25a109.8
N2—C8—C9111.6 (5)C26'—C25—H25a111.7
N2—C8—C9'110.8 (6)C26—C25—H25a109.8
C8—C9—C10108.6 (6)N4—C25—H25b109.8
C9—C10—C11109.0 (7)C26'—C25—H25b98.4
C8—C9'—C10'109.1 (6)C26—C25—H25b109.8
C9'—C10'—C11'108.9 (7)H25a—C25—H25b108.2
N2—C12—C13133.4 (3)C25—C26—H26a110.2
N2—C12—C17106.5 (3)C27—C26—H26a110.2
C13—C12—C17120.0C25—C26—H26b110.2
C12—C13—C14120.0C27—C26—H26b110.2
C15—C14—C13120.0H26a—C26—H26b108.5
C16—C15—C14120.0C28—C27—H27a109.9
C15—C16—C17120.0C26—C27—H27a109.9
N1—C17—C16131.3 (3)C28—C27—H27b109.9
N1—C17—C12108.7 (3)C26—C27—H27b109.9
C16—C17—C12120.0H27a—C27—H27b108.3
O2—C18—C19121.9 (2)C27—C28—H28a109.5
O2—C18—C23118.1 (2)C27—C28—H28b109.5
C19—C18—C23120.0H28a—C28—H28b109.5
C20—C19—C18120.0C27—C28—H28c109.5
C19—C20—C21120.0H28a—C28—H28c109.5
C22—C21—C20120.0H28b—C28—H28c109.5
C21—C22—C23120.0C25—C26'—H26c109.7
C22—C23—C18120.0C27'—C26'—H26c109.7
C22—C23—C24120.4 (2)C25—C26'—H26d109.7
C18—C23—C24119.6 (2)C27'—C26'—H26d109.7
N3—C24—N4111.5 (4)H26c—C26'—H26d108.2
N3—C24—C23124.8 (4)C28'—C27'—H27c109.9
N4—C24—C23123.7 (4)C26'—C27'—H27c109.9
N4—C25—C26109.6 (5)C28'—C27'—H27d109.9
N4—C25—C26'118.1 (8)C26'—C27'—H27d109.9
C25—C26—C27107.4 (6)H27c—C27'—H27d108.3
C28—C27—C26109.0 (7)C27'—C28'—H28d109.5
C25—C26'—C27'109.7 (8)C27'—C28'—H28e109.5
C28'—C27'—C26'109.1 (8)H28d—C28'—H28e109.5
N4—C29—C30133.8 (2)C27'—C28'—H28f109.5
N4—C29—C34106.2 (2)H28d—C28'—H28f109.5
C30—C29—C34120.0H28e—C28'—H28f109.5
C31—C30—C29120.0C31—C30—H30120.0
C30—C31—C32120.0C29—C30—H30120.0
C31—C32—C33120.0C32—C31—H31120.0
C34—C33—C32120.0C30—C31—H31120.0
N3—C34—C33131.4 (2)C33—C32—H32120.0
N3—C34—C29108.6 (2)C31—C32—H32120.0
C33—C34—C29120.0C32—C33—H33120.0
O3—C35—C36122.3 (3)C34—C33—H33120.0
O3—C35—C40117.7 (3)C37—C36—H36120.0
C36—C35—C40120.0C35—C36—H36120.0
C35—C36—C37120.0C36—C37—H37120.0
C38—C37—C36120.0C38—C37—H37120.0
C37—C38—C39120.0C39—C38—H38120.0
C40—C39—C38120.0C37—C38—H38120.0
C39—C40—C35120.0C38—C39—H39120.0
C39—C40—C41119.3 (3)C40—C39—H39120.0
C35—C40—C41120.7 (3)N6—C42—H42a107.7
N5—C41—N6113.2 (5)C43—C42—H42a107.7
N5—C41—C40123.6 (5)C43'—C42—H42a133.8
N6—C41—C40123.2 (5)N6—C42—H42b107.7
N6—C42—C43118.4 (8)C43—C42—H42b107.7
N6—C42—C43'110.2 (7)C43'—C42—H42b85.4
C42—C43—C44110.2 (6)H42a—C42—H42b107.1
C43—C44—C45107.5 (6)C42—C43—H43a109.6
C44'—C43'—C42109.8 (6)C44—C43—H43a109.6
C43'—C44'—C45'109.4 (7)C42—C43—H43b109.6
N6—C46—C47135.3 (4)C44—C43—H43b109.6
N6—C46—C51104.7 (4)H43a—C43—H43b108.1
C47—C46—C51120.0C43—C44—H44a110.2
C46—C47—C48120.0C45—C44—H44a110.2
C47—C48—C49120.0C43—C44—H44b110.2
C50—C49—C48120.0C45—C44—H44b110.2
C49—C50—C51120.0H44a—C44—H44b108.5
N5—C51—C50129.2 (4)C44—C45—H45a109.5
N5—C51—C46110.8 (4)C44—C45—H45b109.5
C50—C51—C46120.0H45a—C45—H45b109.5
C3—C2—H2120.0C44—C45—H45c109.5
C1—C2—H2120.0H45a—C45—H45c109.5
C2—C3—H3120.0H45b—C45—H45c109.5
C4—C3—H3120.0C44'—C43'—H43c109.7
C5—C4—H4120.0C42—C43'—H43c109.7
C3—C4—H4120.0C44'—C43'—H43d109.7
C4—C5—H5120.0C42—C43'—H43d109.7
C6—C5—H5120.0H43c—C43'—H43d108.2
N2—C8—H8a109.3C43'—C44'—H44c109.8
C9—C8—H8a109.3C45'—C44'—H44c109.8
C9'—C8—H8a110.4C43'—C44'—H44d109.8
N2—C8—H8b109.3C45'—C44'—H44d109.8
C9—C8—H8b109.3H44c—C44'—H44d108.2
C9'—C8—H8b109.0C44'—C45'—H45d109.5
H8a—C8—H8b108.0C44'—C45'—H45e109.5
C8—C9—H9a110.0H45d—C45'—H45e109.5
C10—C9—H9a110.0C44'—C45'—H45f109.5
C8—C9—H9b110.0H45d—C45'—H45f109.5
C10—C9—H9b110.0H45e—C45'—H45f109.5
H9a—C9—H9b108.3C46—C47—H47120.0
C9—C10—H10a109.9C48—C47—H47120.0
C11—C10—H10a109.9C49—C48—H48120.0
C9—C10—H10b109.9C47—C48—H48120.0
C11—C10—H10b109.9C48—C49—H49120.0
H10a—C10—H10b108.3C50—C49—H49120.0
C10—C11—H11a109.5C51—C50—H50120.0
C10—C11—H11b109.5C49—C50—H50120.0
O2—Zn1—O1—C1152.8 (2)C29—N4—C24—N30.6 (5)
N3i—Zn1—O1—C183.1 (3)C25—N4—C24—N3179.6 (4)
N1—Zn1—O1—C144.1 (3)C29—N4—C24—C23178.7 (3)
O1—Zn1—O2—C1871.5 (3)C25—N4—C24—C231.1 (7)
N3i—Zn1—O2—C1853.3 (3)C22—C23—C24—N371.0 (5)
N1—Zn1—O2—C18170.9 (3)C18—C23—C24—N3108.5 (4)
O2—Zn1—N1—C7128.1 (3)C22—C23—C24—N4109.9 (4)
O1—Zn1—N1—C715.1 (3)C18—C23—C24—N470.7 (5)
N3i—Zn1—N1—C7103.1 (4)C24—N4—C25—C26'106 (2)
O2—Zn1—N1—C1721.9 (4)C29—N4—C25—C26'75 (2)
O1—Zn1—N1—C17134.9 (3)C24—N4—C25—C2696.7 (9)
N3i—Zn1—N1—C17106.9 (3)C29—N4—C25—C2683.6 (9)
Zn1—O1—C1—C2139.1 (2)N4—C25—C26—C27177 (1)
Zn1—O1—C1—C638.6 (4)C25—C26—C27—C28173 (1)
O1—C1—C2—C3177.7 (3)N4—C25—C26'—C27'163 (1)
C4—C5—C6—C7176.3 (4)C25—C26'—C27'—C28'94 (3)
O1—C1—C6—C5177.6 (3)C24—N4—C29—C30179.0 (3)
O1—C1—C6—C76.1 (4)C25—N4—C29—C300.8 (6)
C2—C1—C6—C7176.2 (4)C24—N4—C29—C340.6 (4)
C17—N1—C7—N22.1 (5)C25—N4—C29—C34179.7 (4)
Zn1—N1—C7—N2157.9 (3)N4—C29—C30—C31179.5 (4)
C17—N1—C7—C6177.1 (4)C24—N3—C34—C33179.1 (3)
Zn1—N1—C7—C621.3 (6)Zn1i—N3—C34—C3315.5 (4)
C12—N2—C7—N10.1 (5)C24—N3—C34—C290.0 (3)
C8—N2—C7—N1164.7 (5)Zn1i—N3—C34—C29163.6 (2)
C12—N2—C7—C6179.0 (4)C32—C33—C34—N3179.1 (3)
C8—N2—C7—C614.5 (8)N4—C29—C34—N30.4 (3)
C5—C6—C7—N1143.0 (4)C30—C29—C34—N3179.3 (3)
C1—C6—C7—N140.7 (6)N4—C29—C34—C33179.6 (3)
C5—C6—C7—N237.9 (6)O3—C35—C36—C37178.1 (3)
C1—C6—C7—N2138.4 (4)C38—C39—C40—C41179.2 (4)
C12—N2—C8—C981.2 (9)O3—C35—C40—C39178.2 (3)
C7—N2—C8—C9116.4 (8)O3—C35—C40—C411.0 (4)
C12—N2—C8—C9'82.1 (8)C36—C35—C40—C41179.2 (4)
C7—N2—C8—C9'115.5 (7)C51—N5—C41—N60.7 (6)
N2—C8—C9—C10177.1 (8)C51—N5—C41—C40178.9 (4)
C8—C9—C10—C1167.7 (12)C46—N6—C41—N50.2 (6)
N2—C8—C9'—C10'156 (1)C42—N6—C41—N5179.6 (5)
C8—C9'—C10'—C11'55 (2)C46—N6—C41—C40178.4 (4)
C7—N2—C12—C13178.6 (3)C42—N6—C41—C401.5 (8)
C8—N2—C12—C1313.0 (6)C39—C40—C41—N565.0 (6)
C7—N2—C12—C171.8 (4)C35—C40—C41—N5114.3 (5)
C8—N2—C12—C17163.8 (4)C39—C40—C41—N6113.0 (5)
N2—C12—C13—C14176.4 (4)C35—C40—C41—N667.8 (5)
C7—N1—C17—C16177.3 (3)C46—N6—C42—C4368.9 (8)
Zn1—N1—C17—C1624.3 (5)C41—N6—C42—C43111.0 (8)
C7—N1—C17—C123.3 (4)C46—N6—C42—C43'99.6 (7)
Zn1—N1—C17—C12156.2 (3)C41—N6—C42—C43'80.2 (8)
C15—C16—C17—N1179.4 (4)N6—C42—C43—C4467 (2)
N2—C12—C17—N13.2 (3)C42—C43—C44—C45164 (1)
C13—C12—C17—N1179.5 (3)N6—C42—C43'—C44'68 (1)
N2—C12—C17—C16177.3 (3)C42—C43'—C44'—C45'178 (2)
Zn1—O2—C18—C1924.9 (4)C41—N6—C46—C47179.7 (4)
Zn1—O2—C18—C23156.1 (2)C42—N6—C46—C470.4 (7)
O2—C18—C19—C20179.0 (3)C41—N6—C46—C510.3 (4)
C21—C22—C23—C24179.5 (3)C42—N6—C46—C51179.8 (4)
O2—C18—C23—C22179.1 (3)N6—C46—C47—C48179.3 (5)
O2—C18—C23—C241.5 (4)C41—N5—C51—C50179.4 (3)
C19—C18—C23—C24179.5 (3)C41—N5—C51—C460.9 (5)
C34—N3—C24—N40.4 (5)C49—C50—C51—N5179.6 (5)
Zn1i—N3—C24—N4164.7 (3)N6—C46—C51—N50.8 (4)
C34—N3—C24—C23178.9 (3)C47—C46—C51—N5179.7 (4)
Zn1i—N3—C24—C2314.6 (5)N6—C46—C51—C50179.5 (4)
Symmetry code: (i) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3o···O10.821.842.660 (4)172

Experimental details

Crystal data
Chemical formula[Zn2(C17H17N2O)4]·2C17H18N2O
Mr1724.71
Crystal system, space groupTriclinic, P1
Temperature (K)295
a, b, c (Å)10.750 (1), 11.839 (1), 18.709 (2)
α, β, γ (°)93.070 (2), 105.927 (1), 103.382 (2)
V3)2210.0 (3)
Z1
Radiation typeMo Kα
µ (mm1)0.61
Crystal size (mm)0.21 × 0.15 × 0.04
Data collection
DiffractometerBruker APEX area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.448, 0.976
No. of measured, independent and
observed [I > 2σ(I)] reflections
11754, 7679, 5409
Rint0.028
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.068, 0.196, 1.02
No. of reflections7679
No. of parameters556
No. of restraints192
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.52, 0.36

Computer programs: SMART (Bruker, 2003), SAINT (Bruker, 2003), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976), SHELXL97.

Selected geometric parameters (Å, º) top
Zn1—O11.963 (3)Zn1—N11.987 (3)
Zn1—O21.904 (3)Zn1—N3i1.981 (3)
O1—Zn1—O2111.3 (1)O2—Zn1—N1106.4 (1)
O1—Zn1—N192.5 (1)O2—Zn1—N3i110.4 (1)
O1—Zn1—N3i111.9 (1)N1—Zn1—N3i123.1 (2)
Symmetry code: (i) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3o···O10.821.842.660 (4)172
 

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