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In the title compound, [Zn(C2N3)2(C12H12N2)2]·0.5C2H6O, the Zn atom is in a distorted octa­hedral environment formed by six N atoms from two 4,4′-dimethyl-2,2′-bipyridine (dmbpy) ligands and two dicyanamide ligands that are cis to one another. There are weak π–π inter­actions between the dmbpy ligands in adjacent mol­ecules [with centroid–centroid distances of 4.175 (3) and 3.838 (3) Å]. One dicyanamide ligand is disordered over two positions with occupancies 0.64 (2):0.36 (2). The ethanol molecule has a half-occupancy.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807025263/pk2021sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807025263/pk2021Isup2.hkl
Contains datablock I

CCDC reference: 654705

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.007 Å
  • Disorder in main residue
  • R factor = 0.057
  • wR factor = 0.206
  • Data-to-parameter ratio = 15.1

checkCIF/PLATON results

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Alert level B PLAT241_ALERT_2_B Check High Ueq as Compared to Neighbors for N6
Alert level C PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.50 Ratio PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.12 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C25 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C26 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C30 PLAT301_ALERT_3_C Main Residue Disorder ......................... 7.00 Perc. PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 50.00 Perc. PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 7
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 64
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 10 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

Polypyridine complexes of transition metals have received much attention in recent years on account of their photophysical properties (Yiting et al., 2001). Hydrogen bonds and π···π stacking interactions have also proven to play important roles in the control of molecular arrangement in the crystalline state and the properties of matter (Jones & Rao, 2001).

The crystal structure of (I) contains half an ethanol molecule for each zinc(II) complex. The Zn atom is coordinated by six N atoms from two chelating dmbpy ligands and two dca ligands that are cis to one another (Fig.1). The Zn—N bond distances range from 2.101 (4) to 2.226 (3) Å and the cis N—Zn—N angles range from 74.87 (13) to 96.25 (13) °, indicating a distorted octahedral coordinated geometry around Zn atom. The dmbpy ligands are planar (maximum deviation from the least-squares planes are 0.0499 (44) Å (for the ligand containing N1 and 0.0436 (50) Å for the ligand containing N3.

The dihedral angle between the two dmbpy ligands is 79.31 (7) °. in the two dca ligands, all the C—N triple bond distances less than 1.13 Å. As depicted in Fig. 2, the complexes are linked via weak π···π stacking interactions between parallel dmbpy ligands to generate a one-dimensional chain along the [100] direction. The center-to-center distance between the pyridyl ring containing atom N1 and that containing N2i atom (i = 1 - x, 1 - y, 1 - z) is 4.175 (3) Å and that between the rings containing atom N3 and atom N4ii (ii = - x, 1 - y, -z) is 3.838 (3) Å. The one-dimensional chains are parallel in the crystal structure of (I) and the ethanol resides in a vacancy between the main complexes.

Related literature top

For related literature, see: Jones & Rao (2001); Yiting et al. (2001).

Experimental top

An ethanol solution (20 ml) of dmbpy (36.8 mg, 0.2 mmol) was added to a mixed aqueous solution (10 ml) of the hexahydrate of zinc(II) perchlorate (37.2 mg, 0.1 mmol) and sodium dicyanamide (17.8 mg, 0.2 mmol) under continuous stirring. After 30 min, the reaction mixture was filtered. Colorless crystals of (I) suitable for X-ray diffraction analysis were obtained by slow evaporation of the filtrate at room temperature. Yield 67%. Spectroscopic analysis: IR (KBr, νcm-1): 3433, 2295, 2231, 2200,2170, 1616, 1562, 1485, 1354, 1120, 1016, 921, 837. (IR spectra were recorded on a BIO-RAD FTS 3000 infrared spectrophotometer). Analysis, required for C58H54N20OZn2: C 59.14, H 4.62, N 23.78%; found: C 59.32, H 4.39, N 23.85%.

Refinement top

The dca ligand containing atom N8 is disordered over two positions with refined site-occupancy factors of 0.64 (2) and 0.36 (2). All H atoms were located in a difference Fourier map and were refined using a riding model, with distances between 0.93–0.97 Å (CH) and an OH distance of 0.82 Å. Uiso(H) values were set to either 1.2Ueq or 1.5Ueq (CH3, OH) of the attached atom.

Structure description top

Polypyridine complexes of transition metals have received much attention in recent years on account of their photophysical properties (Yiting et al., 2001). Hydrogen bonds and π···π stacking interactions have also proven to play important roles in the control of molecular arrangement in the crystalline state and the properties of matter (Jones & Rao, 2001).

The crystal structure of (I) contains half an ethanol molecule for each zinc(II) complex. The Zn atom is coordinated by six N atoms from two chelating dmbpy ligands and two dca ligands that are cis to one another (Fig.1). The Zn—N bond distances range from 2.101 (4) to 2.226 (3) Å and the cis N—Zn—N angles range from 74.87 (13) to 96.25 (13) °, indicating a distorted octahedral coordinated geometry around Zn atom. The dmbpy ligands are planar (maximum deviation from the least-squares planes are 0.0499 (44) Å (for the ligand containing N1 and 0.0436 (50) Å for the ligand containing N3.

The dihedral angle between the two dmbpy ligands is 79.31 (7) °. in the two dca ligands, all the C—N triple bond distances less than 1.13 Å. As depicted in Fig. 2, the complexes are linked via weak π···π stacking interactions between parallel dmbpy ligands to generate a one-dimensional chain along the [100] direction. The center-to-center distance between the pyridyl ring containing atom N1 and that containing N2i atom (i = 1 - x, 1 - y, 1 - z) is 4.175 (3) Å and that between the rings containing atom N3 and atom N4ii (ii = - x, 1 - y, -z) is 3.838 (3) Å. The one-dimensional chains are parallel in the crystal structure of (I) and the ethanol resides in a vacancy between the main complexes.

For related literature, see: Jones & Rao (2001); Yiting et al. (2001).

Computing details top

Data collection: APEX2 (Bruker, 2003); cell refinement: APEX2 or SAINT? (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker 2003); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. View of the assymmetric unit of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. The molecular packing, viewed along c axis.
cis-Bis(4,4'-dimethyl-2,2'-bipyridyl)bis(dicyanamide)zinc(II) ethanol hemisolvate top
Crystal data top
[Zn(C2N3)2(C12H12N2)2]·0.5C2H6OF(000) = 1220
Mr = 589.00Dx = 1.322 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5956 reflections
a = 15.694 (2) Åθ = 2.8–25.4°
b = 14.713 (2) ŵ = 0.87 mm1
c = 13.8868 (19) ÅT = 294 K
β = 112.674 (2)°Block, colourless
V = 2958.7 (7) Å30.24 × 0.20 × 0.16 mm
Z = 4
Data collection top
Bruker APEX II CCD area-detector
diffractometer
6059 independent reflections
Radiation source: fine-focus sealed tube4171 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
φ and ω scansθmax = 26.4°, θmin = 1.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 199
Tmin = 0.772, Tmax = 0.870k = 1817
16800 measured reflectionsl = 1717
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)] = 0.057Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.206H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.1227P)2 + 1.4831P]
where P = (Fo2 + 2Fc2)/3
6059 reflections(Δ/σ)max = 0.003
402 parametersΔρmax = 0.95 e Å3
64 restraintsΔρmin = 0.45 e Å3
Crystal data top
[Zn(C2N3)2(C12H12N2)2]·0.5C2H6OV = 2958.7 (7) Å3
Mr = 589.00Z = 4
Monoclinic, P21/cMo Kα radiation
a = 15.694 (2) ŵ = 0.87 mm1
b = 14.713 (2) ÅT = 294 K
c = 13.8868 (19) Å0.24 × 0.20 × 0.16 mm
β = 112.674 (2)°
Data collection top
Bruker APEX II CCD area-detector
diffractometer
6059 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
4171 reflections with I > 2σ(I)
Tmin = 0.772, Tmax = 0.870Rint = 0.031
16800 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.05764 restraints
wR(F2) = 0.206H-atom parameters constrained
S = 1.08Δρmax = 0.95 e Å3
6059 reflectionsΔρmin = 0.45 e Å3
402 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 > 2σ(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*/UeqOcc. (<1)
Zn10.26488 (3)0.45836 (3)0.21113 (3)0.0488 (2)
N10.3197 (2)0.5743 (2)0.3162 (3)0.0502 (8)
N20.3189 (2)0.3995 (2)0.3645 (3)0.0510 (8)
N30.1999 (2)0.5370 (2)0.0733 (3)0.0481 (8)
N40.1283 (2)0.4973 (3)0.2124 (3)0.0524 (8)
N50.3916 (3)0.4500 (3)0.1909 (3)0.0656 (10)
N60.5474 (4)0.4465 (4)0.1965 (5)0.0952 (15)
N70.6198 (5)0.5372 (4)0.1048 (5)0.1123 (19)
N80.2159 (3)0.3333 (3)0.1376 (3)0.0706 (10)
C10.3184 (3)0.6601 (3)0.2883 (4)0.0604 (11)
H10.29110.67420.21760.073*
C20.3553 (3)0.7299 (3)0.3580 (4)0.0632 (11)
H20.35330.78940.33440.076*
C30.3950 (3)0.7109 (3)0.4623 (4)0.0613 (11)
C40.3968 (3)0.6203 (3)0.4924 (3)0.0599 (11)
H40.42330.60470.56270.072*
C50.3590 (3)0.5535 (3)0.4176 (3)0.0478 (9)
C60.3579 (3)0.4568 (3)0.4447 (3)0.0493 (9)
C70.3940 (3)0.4249 (3)0.5452 (3)0.0582 (10)
H70.42130.46540.59980.070*
C80.3906 (3)0.3331 (3)0.5671 (4)0.0639 (11)
C90.3523 (3)0.2761 (3)0.4843 (4)0.0664 (12)
H90.35040.21390.49520.080*
C100.3168 (3)0.3102 (3)0.3857 (4)0.0601 (11)
H100.29000.27020.33040.072*
C110.4351 (4)0.7839 (4)0.5419 (5)0.0880 (17)
H11A0.46430.82880.51490.132*
H11B0.48000.75780.60430.132*
H11C0.38680.81180.55780.132*
C120.4267 (4)0.3001 (4)0.6780 (4)0.0894 (17)
H12A0.38170.31170.70770.134*
H12B0.48300.33160.71770.134*
H12C0.43860.23600.67960.134*
C130.2371 (3)0.5524 (3)0.0024 (3)0.0574 (11)
H130.29180.52300.01030.069*
C140.1983 (4)0.6092 (3)0.0804 (4)0.0670 (12)
H140.22610.61740.12800.080*
C150.1173 (4)0.6545 (3)0.0936 (4)0.0666 (12)
C160.0785 (3)0.6362 (3)0.0229 (4)0.0620 (11)
H160.02280.66350.03060.074*
C170.1205 (3)0.5779 (3)0.0597 (3)0.0470 (9)
C180.0799 (3)0.5560 (3)0.1380 (3)0.0476 (9)
C190.0018 (3)0.5927 (3)0.1341 (4)0.0567 (10)
H190.03410.63290.08070.068*
C200.0367 (3)0.5707 (3)0.2085 (4)0.0625 (11)
C210.0135 (4)0.5108 (4)0.2844 (4)0.0731 (13)
H210.00710.49380.33630.088*
C220.0943 (4)0.4759 (4)0.2837 (4)0.0676 (12)
H220.12710.43500.33590.081*
C230.0748 (5)0.7225 (4)0.1791 (5)0.102 (2)
H23A0.01820.69840.22920.153*
H23B0.11670.73500.21270.153*
H23C0.06210.77760.15010.153*
C240.1243 (4)0.6141 (4)0.2073 (5)0.0829 (16)
H24A0.16880.56720.20030.124*
H24B0.14810.65500.14910.124*
H24C0.11210.64700.27090.124*
C250.4622 (3)0.4524 (3)0.1893 (3)0.0533 (10)
C260.5817 (4)0.4974 (4)0.1456 (5)0.0753 (14)
C270.1844 (4)0.2722 (3)0.0877 (4)0.0698 (13)
N90.1507 (7)0.2111 (7)0.0119 (11)0.088 (3)0.64 (2)
C280.0769 (4)0.1747 (4)0.0020 (5)0.0834 (16)0.64 (2)
N100.0048 (6)0.1397 (7)0.0195 (11)0.105 (4)0.64 (2)
N9'0.1659 (9)0.1872 (10)0.0591 (15)0.070 (5)0.36 (2)
C28'0.0769 (4)0.1747 (4)0.0020 (5)0.0834 (16)0.36 (2)
N10'0.0058 (8)0.1591 (13)0.0634 (15)0.094 (6)0.36 (2)
C290.7949 (9)0.0355 (7)0.9106 (12)0.096 (4)0.50
H29A0.83880.02260.87970.144*0.50
H29B0.74040.00050.87720.144*0.50
H29C0.82160.02120.98370.144*0.50
C300.7712 (7)0.1294 (7)0.8976 (9)0.077 (3)0.50
H30A0.70520.13460.85780.092*0.50
H30B0.78420.15590.96580.092*0.50
O10.8149 (5)0.1774 (6)0.8501 (7)0.098 (2)0.50
H1A0.83070.14390.81280.147*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.0478 (3)0.0516 (3)0.0448 (3)0.0035 (2)0.0155 (2)0.00216 (19)
N10.055 (2)0.0476 (18)0.0453 (18)0.0068 (15)0.0164 (15)0.0053 (15)
N20.0515 (19)0.0518 (19)0.0479 (18)0.0030 (15)0.0170 (15)0.0007 (15)
N30.0490 (19)0.0537 (19)0.0415 (17)0.0028 (15)0.0173 (15)0.0023 (14)
N40.0475 (19)0.062 (2)0.050 (2)0.0020 (16)0.0210 (16)0.0010 (17)
N50.057 (2)0.078 (3)0.065 (2)0.0031 (19)0.0269 (19)0.0028 (19)
N60.0927 (17)0.0955 (18)0.0974 (18)0.0011 (10)0.0367 (11)0.0035 (10)
N70.111 (2)0.114 (2)0.114 (2)0.0007 (10)0.0455 (12)0.0008 (10)
N80.0700 (13)0.0688 (13)0.0706 (13)0.0009 (9)0.0245 (9)0.0025 (9)
C10.072 (3)0.053 (2)0.056 (2)0.006 (2)0.023 (2)0.002 (2)
C20.068 (3)0.051 (2)0.066 (3)0.007 (2)0.022 (2)0.004 (2)
C30.054 (3)0.056 (2)0.068 (3)0.007 (2)0.017 (2)0.014 (2)
C40.054 (2)0.066 (3)0.049 (2)0.000 (2)0.0090 (19)0.007 (2)
C50.043 (2)0.053 (2)0.045 (2)0.0018 (17)0.0147 (17)0.0053 (17)
C60.044 (2)0.055 (2)0.049 (2)0.0001 (17)0.0187 (18)0.0022 (18)
C70.058 (3)0.066 (3)0.045 (2)0.002 (2)0.0135 (19)0.002 (2)
C80.058 (3)0.073 (3)0.059 (3)0.002 (2)0.020 (2)0.013 (2)
C90.073 (3)0.053 (2)0.075 (3)0.004 (2)0.030 (3)0.012 (2)
C100.068 (3)0.050 (2)0.062 (3)0.006 (2)0.025 (2)0.001 (2)
C110.092 (4)0.071 (3)0.078 (4)0.006 (3)0.007 (3)0.028 (3)
C120.096 (4)0.095 (4)0.068 (3)0.006 (3)0.022 (3)0.030 (3)
C130.057 (3)0.070 (3)0.049 (2)0.001 (2)0.024 (2)0.001 (2)
C140.084 (3)0.069 (3)0.057 (3)0.000 (3)0.037 (3)0.004 (2)
C150.081 (3)0.062 (3)0.054 (3)0.000 (2)0.024 (2)0.004 (2)
C160.066 (3)0.057 (3)0.063 (3)0.009 (2)0.026 (2)0.002 (2)
C170.050 (2)0.045 (2)0.047 (2)0.0037 (17)0.0192 (17)0.0072 (17)
C180.045 (2)0.048 (2)0.047 (2)0.0049 (17)0.0153 (17)0.0085 (17)
C190.054 (2)0.057 (2)0.060 (3)0.0001 (19)0.023 (2)0.008 (2)
C200.053 (3)0.066 (3)0.074 (3)0.007 (2)0.031 (2)0.014 (2)
C210.065 (3)0.091 (4)0.077 (3)0.005 (3)0.042 (3)0.008 (3)
C220.064 (3)0.082 (3)0.064 (3)0.003 (2)0.032 (2)0.011 (2)
C230.125 (5)0.097 (4)0.084 (4)0.032 (4)0.040 (4)0.037 (3)
C240.063 (3)0.096 (4)0.102 (4)0.002 (3)0.045 (3)0.011 (3)
C250.045 (2)0.056 (2)0.054 (2)0.0052 (18)0.0142 (19)0.0010 (18)
C260.061 (3)0.084 (4)0.092 (4)0.006 (3)0.041 (3)0.006 (3)
C270.067 (3)0.057 (3)0.079 (3)0.010 (2)0.021 (3)0.016 (2)
N90.089 (3)0.088 (3)0.088 (3)0.0007 (10)0.0342 (16)0.0016 (10)
C280.078 (4)0.084 (4)0.091 (4)0.009 (3)0.035 (3)0.024 (3)
N100.105 (4)0.105 (4)0.105 (4)0.0011 (10)0.0398 (17)0.0005 (10)
N9'0.070 (5)0.069 (5)0.071 (5)0.0000 (10)0.026 (2)0.0000 (10)
C28'0.078 (4)0.084 (4)0.091 (4)0.009 (3)0.035 (3)0.024 (3)
N10'0.094 (6)0.094 (6)0.094 (6)0.0005 (10)0.036 (2)0.0002 (10)
C290.069 (6)0.106 (7)0.119 (8)0.011 (5)0.041 (6)0.008 (6)
C300.055 (5)0.095 (6)0.080 (6)0.001 (5)0.026 (4)0.003 (5)
O10.071 (4)0.098 (5)0.107 (5)0.004 (4)0.014 (4)0.040 (4)
Geometric parameters (Å, º) top
Zn1—N82.101 (4)C12—H12A0.9600
Zn1—N52.117 (4)C12—H12B0.9600
Zn1—N32.130 (3)C12—H12C0.9600
Zn1—N22.148 (3)C13—C141.360 (6)
Zn1—N12.194 (3)C13—H130.9300
Zn1—N42.226 (3)C14—C151.384 (7)
N1—C11.319 (5)C14—H140.9300
N1—C51.336 (5)C15—C161.367 (6)
N2—C61.342 (5)C15—C231.498 (7)
N2—C101.349 (5)C16—C171.380 (6)
N3—C171.330 (5)C16—H160.9300
N3—C131.342 (5)C17—C181.492 (5)
N4—C221.331 (6)C18—C191.373 (6)
N4—C181.336 (5)C19—C201.382 (6)
N5—C251.118 (6)C19—H190.9300
N6—C261.281 (7)C20—C211.366 (7)
N6—C251.305 (7)C20—C241.510 (6)
N7—C261.132 (7)C21—C221.372 (7)
N8—C271.127 (6)C21—H210.9300
C1—C21.377 (6)C22—H220.9300
C1—H10.9300C23—H23A0.9600
C2—C31.367 (7)C23—H23B0.9600
C2—H20.9300C23—H23C0.9600
C3—C41.393 (6)C24—H24A0.9600
C3—C111.495 (6)C24—H24B0.9600
C4—C51.386 (6)C24—H24C0.9600
C4—H40.9300C27—N9'1.311 (14)
C5—C61.475 (5)C27—N91.329 (10)
C6—C71.371 (6)N9—C281.222 (10)
C7—C81.390 (6)C28—N101.181 (8)
C7—H70.9300C29—C301.425 (9)
C8—C91.361 (7)C29—H29A0.9600
C8—C121.503 (7)C29—H29B0.9600
C9—C101.360 (6)C29—H29C0.9600
C9—H90.9300C30—O11.324 (8)
C10—H100.9300C30—H30A0.9700
C11—H11A0.9600C30—H30B0.9700
C11—H11B0.9600O1—H1A0.8200
C11—H11C0.9600
N8—Zn1—N594.05 (16)C8—C12—H12B109.5
N8—Zn1—N394.59 (14)H12A—C12—H12B109.5
N5—Zn1—N393.49 (14)C8—C12—H12C109.5
N8—Zn1—N293.40 (14)H12A—C12—H12C109.5
N5—Zn1—N294.37 (14)H12B—C12—H12C109.5
N3—Zn1—N2168.36 (13)N3—C13—C14123.0 (4)
N8—Zn1—N1168.71 (14)N3—C13—H13118.5
N5—Zn1—N189.18 (14)C14—C13—H13118.5
N3—Zn1—N196.01 (13)C13—C14—C15119.8 (4)
N2—Zn1—N175.55 (12)C13—C14—H14120.1
N8—Zn1—N493.27 (15)C15—C14—H14120.1
N5—Zn1—N4166.71 (14)C16—C15—C14116.8 (4)
N3—Zn1—N474.87 (13)C16—C15—C23121.0 (5)
N2—Zn1—N496.25 (13)C14—C15—C23122.2 (5)
N1—Zn1—N485.78 (13)C15—C16—C17121.1 (4)
C1—N1—C5118.5 (4)C15—C16—H16119.5
C1—N1—Zn1126.2 (3)C17—C16—H16119.5
C5—N1—Zn1115.2 (3)N3—C17—C16121.4 (4)
C6—N2—C10118.1 (4)N3—C17—C18116.1 (4)
C6—N2—Zn1116.7 (3)C16—C17—C18122.5 (4)
C10—N2—Zn1125.2 (3)N4—C18—C19121.9 (4)
C17—N3—C13117.9 (4)N4—C18—C17115.4 (3)
C17—N3—Zn1118.1 (3)C19—C18—C17122.8 (4)
C13—N3—Zn1123.9 (3)C18—C19—C20120.7 (4)
C22—N4—C18117.2 (4)C18—C19—H19119.6
C22—N4—Zn1127.5 (3)C20—C19—H19119.6
C18—N4—Zn1114.9 (3)C21—C20—C19116.9 (4)
C25—N5—Zn1172.1 (4)C21—C20—C24122.2 (5)
C26—N6—C25123.7 (5)C19—C20—C24120.9 (5)
C27—N8—Zn1171.7 (4)C20—C21—C22119.7 (4)
N1—C1—C2123.6 (4)C20—C21—H21120.2
N1—C1—H1118.2C22—C21—H21120.2
C2—C1—H1118.2N4—C22—C21123.6 (5)
C3—C2—C1119.2 (4)N4—C22—H22118.2
C3—C2—H2120.4C21—C22—H22118.2
C1—C2—H2120.4C15—C23—H23A109.5
C2—C3—C4117.5 (4)C15—C23—H23B109.5
C2—C3—C11121.7 (5)H23A—C23—H23B109.5
C4—C3—C11120.7 (5)C15—C23—H23C109.5
C5—C4—C3120.0 (4)H23A—C23—H23C109.5
C5—C4—H4120.0H23B—C23—H23C109.5
C3—C4—H4120.0C20—C24—H24A108.7
N1—C5—C4121.2 (4)C20—C24—H24B109.4
N1—C5—C6116.3 (4)H24A—C24—H24B109.5
C4—C5—C6122.5 (4)C20—C24—H24C110.2
N2—C6—C7120.5 (4)H24A—C24—H24C109.5
N2—C6—C5116.2 (4)H24B—C24—H24C109.5
C7—C6—C5123.3 (4)N5—C25—N6172.4 (5)
C6—C7—C8121.3 (4)N7—C26—N6173.0 (7)
C6—C7—H7119.3N8—C27—N9'160.3 (10)
C8—C7—H7119.3N8—C27—N9166.7 (8)
C9—C8—C7117.1 (4)C28—N9—C27119.0 (8)
C9—C8—C12122.4 (5)N10—C28—N9177.5 (10)
C7—C8—C12120.4 (5)C30—C29—H29A109.5
C10—C9—C8119.9 (4)C30—C29—H29B109.5
C10—C9—H9120.0H29A—C29—H29B109.5
C8—C9—H9120.0C30—C29—H29C109.5
N2—C10—C9123.0 (4)H29A—C29—H29C109.5
N2—C10—H10118.5H29B—C29—H29C109.5
C9—C10—H10118.5O1—C30—C29114.8 (9)
C3—C11—H11A109.5O1—C30—H30A108.6
C3—C11—H11B109.5C29—C30—H30A108.6
H11A—C11—H11B109.5O1—C30—H30B108.6
C3—C11—H11C109.5C29—C30—H30B108.6
H11A—C11—H11C109.5H30A—C30—H30B107.5
H11B—C11—H11C109.5C30—O1—H1A109.6
C8—C12—H12A109.5
N8—Zn1—N1—C1167.9 (7)C3—C4—C5—N10.7 (7)
N5—Zn1—N1—C185.3 (4)C3—C4—C5—C6179.3 (4)
N3—Zn1—N1—C18.1 (4)C10—N2—C6—C70.4 (6)
N2—Zn1—N1—C1180.0 (4)Zn1—N2—C6—C7179.9 (3)
N4—Zn1—N1—C182.4 (4)C10—N2—C6—C5179.6 (4)
N8—Zn1—N1—C513.2 (9)Zn1—N2—C6—C50.1 (5)
N5—Zn1—N1—C593.6 (3)N1—C5—C6—N21.1 (5)
N3—Zn1—N1—C5173.0 (3)C4—C5—C6—N2179.8 (4)
N2—Zn1—N1—C51.1 (3)N1—C5—C6—C7178.9 (4)
N4—Zn1—N1—C598.7 (3)C4—C5—C6—C70.2 (7)
N8—Zn1—N2—C6178.2 (3)N2—C6—C7—C80.6 (7)
N5—Zn1—N2—C687.5 (3)C5—C6—C7—C8179.4 (4)
N3—Zn1—N2—C644.8 (8)C6—C7—C8—C91.8 (7)
N1—Zn1—N2—C60.5 (3)C6—C7—C8—C12177.2 (5)
N4—Zn1—N2—C684.5 (3)C7—C8—C9—C102.1 (7)
N8—Zn1—N2—C102.1 (4)C12—C8—C9—C10177.0 (5)
N5—Zn1—N2—C1092.2 (4)C6—N2—C10—C90.1 (7)
N3—Zn1—N2—C10135.5 (6)Zn1—N2—C10—C9179.8 (3)
N1—Zn1—N2—C10179.8 (4)C8—C9—C10—N21.2 (7)
N4—Zn1—N2—C1095.8 (4)C17—N3—C13—C141.6 (6)
N8—Zn1—N3—C1799.3 (3)Zn1—N3—C13—C14174.2 (3)
N5—Zn1—N3—C17166.3 (3)N3—C13—C14—C150.6 (7)
N2—Zn1—N3—C1733.9 (8)C13—C14—C15—C162.5 (7)
N1—Zn1—N3—C1776.8 (3)C13—C14—C15—C23175.8 (5)
N4—Zn1—N3—C177.2 (3)C14—C15—C16—C172.4 (7)
N8—Zn1—N3—C1385.0 (3)C23—C15—C16—C17175.9 (5)
N5—Zn1—N3—C139.4 (3)C13—N3—C17—C161.7 (6)
N2—Zn1—N3—C13141.8 (6)Zn1—N3—C17—C16174.3 (3)
N1—Zn1—N3—C1398.9 (3)C13—N3—C17—C18177.7 (3)
N4—Zn1—N3—C13177.1 (3)Zn1—N3—C17—C186.3 (4)
N8—Zn1—N4—C2285.9 (4)C15—C16—C17—N30.4 (7)
N5—Zn1—N4—C22150.8 (6)C15—C16—C17—C18179.7 (4)
N3—Zn1—N4—C22179.7 (4)C22—N4—C18—C190.3 (6)
N2—Zn1—N4—C227.9 (4)Zn1—N4—C18—C19174.1 (3)
N1—Zn1—N4—C2282.9 (4)C22—N4—C18—C17179.9 (4)
N8—Zn1—N4—C18101.0 (3)Zn1—N4—C18—C176.3 (4)
N5—Zn1—N4—C1822.3 (8)N3—C17—C18—N40.3 (5)
N3—Zn1—N4—C187.1 (3)C16—C17—C18—N4179.1 (4)
N2—Zn1—N4—C18165.2 (3)N3—C17—C18—C19179.8 (4)
N1—Zn1—N4—C1890.3 (3)C16—C17—C18—C190.5 (6)
C5—N1—C1—C20.1 (7)N4—C18—C19—C200.7 (6)
Zn1—N1—C1—C2179.0 (3)C17—C18—C19—C20179.8 (4)
N1—C1—C2—C30.7 (8)C18—C19—C20—C210.5 (7)
C1—C2—C3—C40.8 (7)C18—C19—C20—C24177.3 (4)
C1—C2—C3—C11179.2 (5)C19—C20—C21—C220.0 (8)
C2—C3—C4—C50.1 (7)C24—C20—C21—C22177.7 (5)
C11—C3—C4—C5179.8 (5)C18—N4—C22—C210.2 (7)
C1—N1—C5—C40.8 (6)Zn1—N4—C22—C21172.8 (4)
Zn1—N1—C5—C4179.8 (3)C20—C21—C22—N40.4 (8)
C1—N1—C5—C6179.5 (4)N8—C27—N9—C28134 (3)
Zn1—N1—C5—C61.5 (5)N9'—C27—N9—C2872.4 (17)

Experimental details

Crystal data
Chemical formula[Zn(C2N3)2(C12H12N2)2]·0.5C2H6O
Mr589.00
Crystal system, space groupMonoclinic, P21/c
Temperature (K)294
a, b, c (Å)15.694 (2), 14.713 (2), 13.8868 (19)
β (°) 112.674 (2)
V3)2958.7 (7)
Z4
Radiation typeMo Kα
µ (mm1)0.87
Crystal size (mm)0.24 × 0.20 × 0.16
Data collection
DiffractometerBruker APEX II CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.772, 0.870
No. of measured, independent and
observed [I > 2σ(I)] reflections
16800, 6059, 4171
Rint0.031
(sin θ/λ)max1)0.626
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.057, 0.206, 1.08
No. of reflections6059
No. of parameters402
No. of restraints64
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.95, 0.45

Computer programs: APEX2 (Bruker, 2003), APEX2 or SAINT? (Bruker, 2003), SAINT (Bruker, 2003), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker 2003), SHELXTL.

 

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