Download citation
Download citation
link to html
A new six-coordinate monomeric ZnII complex, [Zn(L)3](NO3)2, where L is 4,4′,5,5′-tetra­methyl-2,2′-bi­imidazole (C10H14N4), has been synthesized and characterized by X-ray diffraction techniques. The ZnII atom, on a twofold axis, has a ZnN6 distorted octahedral coordination environment. 4,4′,5,5′-Tetra­methyl-2,2′-bi­imidazole is bonded as a chelating ligand through its unprotonated N atoms. These discrete monomeric units possesses excellent hydrogen-bonding sites which further self-assemble into a three-dimensional supramolecular architecture through intermolecular N—H...O and C—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805013954/is6066sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805013954/is6066Isup2.hkl
Contains datablock I

CCDC reference: 274440

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.043
  • wR factor = 0.111
  • Data-to-parameter ratio = 16.1

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT222_ALERT_3_A Large Non-Solvent H Ueq(max)/Ueq(min) ... 5.33 Ratio
Alert level C RINTA01_ALERT_3_C The value of Rint is greater than 0.10 Rint given 0.116 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.12 PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.23 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N7 PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C14 PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of . 70.00 A   3
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 28.29 From the CIF: _reflns_number_total 4093 Count of symmetry unique reflns 2410 Completeness (_total/calc) 169.83% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1683 Fraction of Friedel pairs measured 0.698 Are heavy atom types Z>Si present yes
1 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 10 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 4 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

Tris(4,4',5,5'-tetramethyl-2,2'-biimidazole)zinc(II) dinitrate top
Crystal data top
[Zn(C10H14N4)3](NO3)2Dx = 1.346 Mg m3
Mr = 760.15Mo Kα radiation, λ = 0.71073 Å
Hexagonal, P64Cell parameters from 6512 reflections
a = 13.900 (2) Åθ = 2.9–24.1°
c = 16.809 (3) ŵ = 0.72 mm1
V = 2812.7 (8) Å3T = 293 K
Z = 3Block, red
F(000) = 11940.20 × 0.20 × 0.15 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
4093 independent reflections
Radiation source: fine-focus sealed tube3093 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.116
Detector resolution: 8.366 pixels mm-1θmax = 28.3°, θmin = 1.7°
φ and ω scansh = 1218
Absorption correction: multi-scan
(SADABS; Bruker, 1998)
k = 1815
Tmin = 0.868, Tmax = 0.898l = 1721
17035 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043H-atom parameters constrained
wR(F2) = 0.111 w = 1/[σ2(Fo2) + (0.0565P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.96(Δ/σ)max < 0.001
4093 reflectionsΔρmax = 0.68 e Å3
254 parametersΔρmin = 0.31 e Å3
1 restraintAbsolute structure: Flack (1983), 1683 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.027 (13)
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
Zn10.50000.50000.17471 (3)0.05577 (14)
C10.6948 (2)0.6142 (3)0.0302 (2)0.0631 (7)
C20.7235 (3)0.7016 (3)0.0192 (2)0.0690 (8)
C30.5999 (2)0.6903 (2)0.06630 (18)0.0547 (6)
C40.5190 (2)0.7054 (2)0.11051 (18)0.0537 (6)
C50.4118 (3)0.7647 (3)0.1567 (2)0.0660 (8)
C60.3870 (2)0.6676 (3)0.19359 (18)0.0602 (7)
C70.7377 (4)0.5361 (4)0.0327 (3)0.0853 (11)
H7A0.67860.46240.02080.124 (18)*
H7B0.76630.53710.08490.101 (15)*
H7C0.79590.55800.00580.110 (14)*
C80.7982 (4)0.7433 (5)0.0887 (3)0.1006 (14)
H8A0.83150.69810.09710.19 (3)*
H8B0.85530.81870.07920.090 (13)*
H8C0.75640.74040.13500.18 (3)*
C90.3652 (4)0.8406 (4)0.1662 (3)0.0975 (14)
H9A0.28780.79780.17950.097 (12)*
H9B0.37370.87970.11730.088 (12)*
H9C0.40430.89310.20790.32 (6)*
C100.3023 (3)0.6062 (3)0.2551 (3)0.0779 (10)
H10A0.26740.64820.27020.092 (12)*
H10B0.33700.59520.30080.13 (2)*
H10C0.24730.53550.23430.118 (17)*
C110.2728 (3)0.3279 (3)0.3719 (3)0.0809 (10)
C120.2826 (3)0.3402 (3)0.2912 (2)0.0713 (9)
C130.4431 (3)0.4572 (3)0.3424 (2)0.0676 (8)
C140.1718 (5)0.2489 (5)0.4200 (3)0.1225 (18)
H14A0.18990.25900.47560.184*
H14B0.14890.17380.40510.184*
H14C0.11250.26370.40970.184*
C150.1956 (3)0.2814 (4)0.2278 (3)0.0860 (11)
H15A0.12880.22400.25180.14 (2)*
H15B0.22240.24910.18960.096 (13)*
H15C0.18030.33370.20170.096 (14)*
N10.6162 (2)0.6072 (2)0.08389 (16)0.0578 (6)
N20.45547 (18)0.63124 (19)0.16345 (16)0.0554 (5)
N30.4953 (2)0.7866 (2)0.10390 (16)0.0618 (6)
H3A0.52660.84260.07230.060 (9)*
N40.6626 (2)0.7494 (2)0.00532 (17)0.0624 (6)
H4A0.66460.80710.01510.072 (10)*
N50.3904 (2)0.4200 (2)0.27343 (17)0.0642 (6)
N60.3722 (3)0.4018 (3)0.4034 (2)0.0811 (9)
H6A0.38790.41210.45330.16 (3)*
N70.9754 (2)0.3546 (3)0.2781 (2)0.0815 (9)
O10.9869 (3)0.3607 (4)0.3503 (2)0.1347 (15)
O21.0435 (2)0.4214 (3)0.2309 (2)0.1163 (11)
O30.8911 (3)0.2796 (2)0.2513 (2)0.1055 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.0570 (3)0.0602 (3)0.0561 (2)0.0338 (2)0.0000.000
C10.0560 (15)0.0766 (18)0.0615 (17)0.0366 (15)0.0040 (14)0.0008 (15)
C20.0590 (16)0.086 (2)0.0663 (19)0.0395 (16)0.0103 (15)0.0047 (17)
C30.0489 (14)0.0591 (15)0.0550 (15)0.0262 (12)0.0049 (13)0.0024 (13)
C40.0545 (14)0.0557 (14)0.0536 (15)0.0297 (12)0.0026 (13)0.0034 (13)
C50.0655 (17)0.0639 (17)0.074 (2)0.0368 (14)0.0057 (16)0.0038 (16)
C60.0574 (15)0.0658 (16)0.0626 (18)0.0348 (13)0.0053 (13)0.0056 (15)
C70.086 (2)0.106 (3)0.088 (3)0.067 (2)0.021 (2)0.009 (2)
C80.101 (3)0.125 (4)0.098 (3)0.074 (3)0.035 (3)0.029 (3)
C90.114 (3)0.092 (3)0.115 (4)0.073 (2)0.043 (3)0.023 (3)
C100.0674 (19)0.071 (2)0.098 (3)0.0369 (18)0.025 (2)0.0087 (19)
C110.082 (2)0.080 (2)0.089 (3)0.047 (2)0.024 (2)0.020 (2)
C120.076 (2)0.071 (2)0.080 (2)0.0462 (18)0.0135 (18)0.0096 (18)
C130.090 (2)0.0718 (17)0.0630 (18)0.0565 (16)0.0125 (18)0.0107 (17)
C140.129 (4)0.117 (4)0.100 (4)0.046 (3)0.037 (3)0.034 (3)
C150.079 (2)0.082 (2)0.098 (3)0.041 (2)0.004 (2)0.009 (2)
N10.0575 (13)0.0668 (14)0.0560 (13)0.0363 (11)0.0043 (11)0.0020 (11)
N20.0530 (11)0.0583 (12)0.0586 (14)0.0307 (10)0.0009 (11)0.0061 (11)
N30.0693 (15)0.0602 (14)0.0623 (15)0.0373 (12)0.0063 (12)0.0047 (12)
N40.0618 (13)0.0696 (14)0.0608 (14)0.0365 (12)0.0081 (13)0.0129 (14)
N50.0745 (16)0.0661 (14)0.0636 (16)0.0439 (14)0.0054 (13)0.0063 (13)
N60.103 (2)0.094 (2)0.0638 (19)0.062 (2)0.0129 (17)0.0149 (16)
N70.0563 (16)0.099 (2)0.075 (2)0.0273 (16)0.0004 (16)0.0075 (18)
O10.0894 (19)0.212 (4)0.068 (2)0.049 (2)0.0029 (16)0.022 (2)
O20.0803 (17)0.119 (2)0.099 (2)0.0118 (17)0.0190 (18)0.0052 (19)
O30.100 (2)0.0918 (19)0.087 (2)0.0202 (17)0.0072 (17)0.0084 (16)
Geometric parameters (Å, º) top
Zn1—N5i2.149 (3)C9—H9A0.9600
Zn1—N52.149 (3)C9—H9B0.9600
Zn1—N1i2.180 (3)C9—H9C0.9600
Zn1—N12.180 (3)C10—H10A0.9600
Zn1—N22.208 (2)C10—H10B0.9600
Zn1—N2i2.208 (2)C10—H10C0.9600
C1—C21.356 (5)C11—N61.351 (6)
C1—N11.383 (4)C11—C121.365 (6)
C1—C71.477 (5)C11—C141.512 (6)
C2—N41.375 (4)C12—N51.380 (5)
C2—C81.476 (6)C12—C151.509 (6)
C3—N11.318 (4)C13—N51.331 (5)
C3—N41.330 (4)C13—N61.363 (5)
C3—C41.448 (4)C13—C13i1.426 (7)
C4—N21.313 (4)C14—H14A0.9600
C4—N31.329 (4)C14—H14B0.9600
C5—C61.364 (5)C14—H14C0.9600
C5—N31.370 (4)C15—H15A0.9600
C5—C91.497 (5)C15—H15B0.9600
C6—N21.378 (4)C15—H15C0.9600
C6—C101.476 (5)N3—H3A0.8600
C7—H7A0.9600N4—H4A0.8600
C7—H7B0.9600N6—H6A0.8600
C7—H7C0.9600N7—O31.202 (4)
C8—H8A0.9600N7—O11.221 (5)
C8—H8B0.9600N7—O21.228 (4)
C8—H8C0.9600
N5i—Zn1—N578.88 (16)H9B—C9—H9C109.5
N5i—Zn1—N1i170.31 (10)C6—C10—H10A109.5
N5—Zn1—N1i95.51 (10)C6—C10—H10B109.5
N5i—Zn1—N195.51 (10)H10A—C10—H10B109.5
N5—Zn1—N1170.31 (10)C6—C10—H10C109.5
N1i—Zn1—N191.09 (14)H10A—C10—H10C109.5
N5i—Zn1—N293.33 (9)H10B—C10—H10C109.5
N5—Zn1—N294.26 (9)N6—C11—C12107.1 (4)
N1i—Zn1—N294.97 (9)N6—C11—C14124.6 (4)
N1—Zn1—N278.07 (9)C12—C11—C14128.3 (5)
N5i—Zn1—N2i94.26 (9)C11—C12—N5108.5 (4)
N5—Zn1—N2i93.33 (9)C11—C12—C15129.1 (4)
N1i—Zn1—N2i78.07 (9)N5—C12—C15122.4 (3)
N1—Zn1—N2i94.97 (9)N5—C13—N6109.5 (3)
N2—Zn1—N2i170.17 (14)N5—C13—C13i119.3 (2)
C2—C1—N1109.3 (3)N6—C13—C13i131.2 (2)
C2—C1—C7129.1 (3)C11—C14—H14A109.5
N1—C1—C7121.6 (3)C11—C14—H14B109.5
C1—C2—N4105.9 (3)H14A—C14—H14B109.5
C1—C2—C8132.1 (3)C11—C14—H14C109.5
N4—C2—C8122.0 (3)H14A—C14—H14C109.5
N1—C3—N4111.6 (3)H14B—C14—H14C109.5
N1—C3—C4119.9 (3)C12—C15—H15A109.5
N4—C3—C4128.5 (3)C12—C15—H15B109.5
N2—C4—N3111.6 (3)H15A—C15—H15B109.5
N2—C4—C3120.0 (2)C12—C15—H15C109.5
N3—C4—C3128.3 (3)H15A—C15—H15C109.5
C6—C5—N3106.3 (2)H15B—C15—H15C109.5
C6—C5—C9131.7 (3)C3—N1—C1105.5 (3)
N3—C5—C9122.0 (3)C3—N1—Zn1111.30 (19)
C5—C6—N2108.5 (3)C1—N1—Zn1142.6 (2)
C5—C6—C10128.6 (3)C4—N2—C6106.1 (2)
N2—C6—C10122.9 (3)C4—N2—Zn1110.51 (18)
C1—C7—H7A109.5C6—N2—Zn1143.3 (2)
C1—C7—H7B109.5C4—N3—C5107.4 (3)
H7A—C7—H7B109.5C4—N3—H3A126.3
C1—C7—H7C109.5C5—N3—H3A126.3
H7A—C7—H7C109.5C3—N4—C2107.7 (3)
H7B—C7—H7C109.5C3—N4—H4A126.1
C2—C8—H8A109.5C2—N4—H4A126.1
C2—C8—H8B109.5C13—N5—C12106.8 (3)
H8A—C8—H8B109.5C13—N5—Zn1111.2 (2)
C2—C8—H8C109.5C12—N5—Zn1142.0 (3)
H8A—C8—H8C109.5C11—N6—C13108.1 (4)
H8B—C8—H8C109.5C11—N6—H6A125.9
C5—C9—H9A109.5C13—N6—H6A125.9
C5—C9—H9B109.5O3—N7—O1118.0 (4)
H9A—C9—H9B109.5O3—N7—O2117.5 (4)
C5—C9—H9C109.5O1—N7—O2124.4 (4)
H9A—C9—H9C109.5
N1—C1—C2—N40.7 (4)C5—C6—N2—Zn1177.1 (3)
C7—C1—C2—N4177.6 (4)C10—C6—N2—Zn13.3 (5)
N1—C1—C2—C8176.6 (4)N5i—Zn1—N2—C494.5 (2)
C7—C1—C2—C85.1 (7)N5—Zn1—N2—C4173.5 (2)
N1—C3—C4—N25.6 (4)N1i—Zn1—N2—C490.6 (2)
N4—C3—C4—N2172.3 (3)N1—Zn1—N2—C40.48 (19)
N1—C3—C4—N3176.5 (3)N5i—Zn1—N2—C682.4 (3)
N4—C3—C4—N35.6 (5)N5—Zn1—N2—C63.3 (3)
N3—C5—C6—N20.3 (3)N1i—Zn1—N2—C692.6 (3)
C9—C5—C6—N2179.4 (4)N1—Zn1—N2—C6177.3 (3)
N3—C5—C6—C10179.3 (3)N2—C4—N3—C50.8 (3)
C9—C5—C6—C101.1 (7)C3—C4—N3—C5178.8 (3)
N6—C11—C12—N52.1 (4)C6—C5—N3—C40.6 (3)
C14—C11—C12—N5178.6 (4)C9—C5—N3—C4179.0 (4)
N6—C11—C12—C15177.6 (3)N1—C3—N4—C20.4 (3)
C14—C11—C12—C151.8 (7)C4—C3—N4—C2177.6 (3)
N4—C3—N1—C10.0 (3)C1—C2—N4—C30.7 (4)
C4—C3—N1—C1178.3 (3)C8—C2—N4—C3177.0 (4)
N4—C3—N1—Zn1173.5 (2)N6—C13—N5—C121.0 (3)
C4—C3—N1—Zn14.7 (3)C13i—C13—N5—C12178.9 (3)
C2—C1—N1—C30.5 (4)N6—C13—N5—Zn1177.79 (18)
C7—C1—N1—C3178.0 (3)C13i—C13—N5—Zn12.4 (4)
C2—C1—N1—Zn1169.6 (3)C11—C12—N5—C131.9 (4)
C7—C1—N1—Zn111.9 (6)C15—C12—N5—C13177.8 (3)
N5i—Zn1—N1—C394.5 (2)C11—C12—N5—Zn1176.3 (3)
N1i—Zn1—N1—C392.6 (2)C15—C12—N5—Zn14.1 (5)
N2—Zn1—N1—C32.3 (2)N5i—Zn1—N5—C130.8 (3)
N2i—Zn1—N1—C3170.7 (2)N1i—Zn1—N5—C13171.2 (2)
N5i—Zn1—N1—C195.8 (4)N2—Zn1—N5—C1393.4 (2)
N1i—Zn1—N1—C177.1 (3)N2i—Zn1—N5—C1392.9 (2)
N2—Zn1—N1—C1172.0 (4)N5i—Zn1—N5—C12178.9 (4)
N2i—Zn1—N1—C11.0 (4)N1i—Zn1—N5—C126.9 (3)
N3—C4—N2—C60.6 (3)N2—Zn1—N5—C1288.5 (3)
C3—C4—N2—C6178.8 (3)N2i—Zn1—N5—C1285.2 (3)
N3—C4—N2—Zn1178.7 (2)C12—C11—N6—C131.4 (4)
C3—C4—N2—Zn13.1 (3)C14—C11—N6—C13179.2 (4)
C5—C6—N2—C40.2 (3)N5—C13—N6—C110.3 (3)
C10—C6—N2—C4179.8 (3)C13i—C13—N6—C11179.9 (4)
Symmetry code: (i) x+1, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3A···O1ii0.862.012.852 (4)167
N4—H4A···O3ii0.862.012.818 (5)156
N6—H6A···O2iii0.862.032.849 (5)157
N6—H6A···O3iii0.862.603.276 (5)136
C9—H9A···O3i0.962.473.403 (7)163
C9—H9B···O1iv0.962.513.431 (7)162
C10—H10C···O2v0.962.463.235 (6)138
Symmetry codes: (i) x+1, y+1, z; (ii) xy, x, z1/3; (iii) y, x+y+1, z+1/3; (iv) x+y+1, x+2, z1/3; (v) x1, y, z.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds