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The title compound, [Zn(C15H21O3)2(C2H6O)2], is a powerful charge-control agent used widely in electrophotography. The present ZnII complex has C2 symmetry and exhibits a deformed octahedral coordination. Two O atoms of the ethanol molecules are coordinated in a cis fashion to the Zn atom.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803020877/ob6306sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803020877/ob6306Isup2.hkl
Contains datablock I

CCDC reference: 225691

Key indicators

  • Single-crystal X-ray study
  • T = 93 K
  • Mean [sigma](C-C) = 0.004 Å
  • H-atom completeness 97%
  • R factor = 0.042
  • wR factor = 0.126
  • Data-to-parameter ratio = 15.8

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.93
Alert level B PLAT430_ALERT_2_B Short Inter D...A Contact O1 .. O4 = 2.62 Ang.
Alert level C REFLT03_ALERT_3_C Reflection count < 95% complete From the CIF: _diffrn_reflns_theta_max 68.22 From the CIF: _diffrn_reflns_theta_full 0.00 From the CIF: _reflns_number_total 3054 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 3301 Completeness (_total/calc) 92.52% PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low .... 0.93 PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)... ? PLAT250_ALERT_2_C Large U3/U1 ratio for average U(i,j) tensor .... 2.29 PLAT301_ALERT_3_C Main Residue Disorder ......................... 9.00 Perc.
Alert level G FORMU01_ALERT_2_G There is a discrepancy between the atom counts in the _chemical_formula_sum and the formula from the _atom_site* data. Atom count from _chemical_formula_sum:C34 H54 O8 Zn1 Atom count from the _atom_site data: C34 H52 O8 Zn1 CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected. CELLZ01_ALERT_1_G WARNING: H atoms missing from atom site list. Is this intentional? From the CIF: _cell_formula_units_Z 4 From the CIF: _chemical_formula_sum C34 H54 O8 Zn TEST: Compare cell contents of formula and atom_site data atom Z*formula cif sites diff C 136.00 136.00 0.00 H 216.00 208.00 8.00 O 32.00 32.00 0.00 Zn 4.00 4.00 0.00 REFLT03_ALERT_1_G ALERT: Expected hkl max differ from CIF values From the CIF: _diffrn_reflns_theta_max 68.22 From the CIF: _reflns_number_total 3054 From the CIF: _diffrn_reflns_limit_ max hkl 40. 13. 9. From the CIF: _diffrn_reflns_limit_ min hkl -40. -13. -9. TEST1: Expected hkl limits for theta max Calculated maximum hkl 40. 13. 11. Calculated minimum hkl -40. -13. -11.
1 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 4 ALERT level G = General alerts; check 6 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 4 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: TEXSAN (Molecular Structure Corporation, 2001); program(s) used to solve structure: SHELXS86 (Sheldrick, 1985); program(s) used to refine structure: TEXSAN; molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: TEXSAN.

(I) top
Crystal data top
[Zn(C15H21O3)2(C2H6O)2]F(000) = 1408
Mr = 656.18Dx = 1.213 Mg m3
Monoclinic, C2/cCu Kα radiation, λ = 1.5418 Å
Hall symbol: -C 2ycCell parameters from 15255 reflections
a = 33.891 (4) Åθ = 4.2–68.1°
b = 11.191 (1) ŵ = 1.32 mm1
c = 9.491 (1) ÅT = 93 K
β = 93.75 (1)°Needle, colourless
V = 3592.1 (7) Å30.45 × 0.10 × 0.10 mm
Z = 4
Data collection top
Rigaku RAXIS-RAPID imaging-plate
diffractometer
2621 reflections with F2 > 2σ(F2)
Detector resolution: 10.00 pixels mm-1Rint = 0.040
48 frames, delta ω = 15 deg scansθmax = 68.2°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 4040
Tmin = 0.548, Tmax = 0.877k = 1313
16078 measured reflectionsl = 99
3054 independent reflections
Refinement top
Refinement on F2H-atom parameters not refined
R[F2 > 2σ(F2)] = 0.042 w = 1/[σ2(Fo2) + (0.05(Max(Fo2,0) + 2Fc2)/3)2]
wR(F2) = 0.126(Δ/σ)max = 0.009
S = 1.65Δρmax = 0.37 e Å3
3054 reflectionsΔρmin = 0.25 e Å3
193 parameters
Special details top

Refinement. Refinement using reflections with F2 > -3.0 σ(F2). The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Zn10.00000.92382 (4)0.25000.0245 (1)
O10.02843 (6)1.0677 (2)0.3851 (2)0.0344 (6)
O20.05906 (5)0.9635 (2)0.2309 (2)0.0332 (6)
O30.12961 (6)1.0184 (2)0.1691 (2)0.0409 (6)
O40.00098 (5)0.8043 (2)0.4112 (2)0.0280 (5)
C10.05959 (9)1.0472 (3)0.3229 (3)0.0337 (8)
C20.09628 (9)1.1185 (3)0.3532 (3)0.0349 (8)
C30.12952 (9)1.1009 (3)0.2724 (3)0.0358 (9)
C40.16369 (9)1.1724 (3)0.3002 (3)0.0357 (8)
C50.16261 (9)1.2567 (3)0.4070 (3)0.0376 (9)
C60.13006 (9)1.2762 (3)0.4872 (3)0.0354 (8)
C70.09714 (9)1.2054 (3)0.4566 (3)0.0354 (8)
C80.20034 (9)1.1553 (3)0.2139 (3)0.0388 (9)
C90.18932 (9)1.1828 (3)0.0570 (3)0.0398 (9)
C100.23363 (9)1.2415 (3)0.2632 (4)0.048 (1)
C110.21647 (9)1.0288 (3)0.2309 (4)0.049 (1)
C120.13065 (10)1.3671 (3)0.6085 (3)0.0397 (9)
C130.1656 (1)1.4541 (4)0.6059 (4)0.070 (1)
C140.1344 (1)1.2990 (3)0.7487 (3)0.048 (1)
C150.0926 (1)1.4401 (3)0.6003 (4)0.065 (1)
C160.0317 (2)0.7186 (6)0.4332 (8)0.033 (1)*0.50
C170.0634 (2)0.7698 (5)0.5338 (7)0.037 (1)*0.50
C180.0332 (2)0.7505 (6)0.4883 (8)0.037 (2)*0.50
C190.0213 (2)0.6751 (6)0.6102 (8)0.049 (2)*0.50
H10.10570.98240.17450.0514*
H20.07441.21690.50850.0425*
H30.18551.30440.42700.0451*
H40.22461.01500.32720.0586*
H50.19640.97320.20140.0586*
H60.23841.01940.17460.0586*
H70.16861.13120.02300.0478*
H80.21181.17070.00380.0478*
H90.18081.26350.04760.0478*
H100.24121.22680.35970.0571*
H110.25571.22940.20800.0571*
H120.22461.32150.25220.0571*
H130.11231.24740.75450.0581*
H140.15801.25320.75380.0581*
H150.13511.35430.82480.0581*
H160.07061.38810.60680.0785*
H170.09021.48180.51300.0785*
H180.09331.49580.67590.0785*
H190.16511.50760.68350.0836*
H200.18971.41040.61260.0836*
H210.16381.49810.52020.0836*
H220.02310.64400.46890.0400*0.50
H230.04350.70160.34400.0400*0.50
H240.08450.71430.54640.0444*0.50
H250.07280.84220.49640.0444*0.50
H260.05270.78510.62220.0444*0.50
H270.04640.70010.42350.0438*0.50
H280.05080.81120.52100.0438*0.50
H290.01030.74100.65700.0584*0.50
H300.00310.61060.60620.0584*0.50
H310.04510.65100.66050.0584*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.0231 (3)0.0225 (3)0.0282 (3)0.00000.0042 (2)0.0000
O10.041 (1)0.039 (1)0.024 (1)0.0175 (9)0.0096 (8)0.0073 (9)
O20.0318 (10)0.040 (1)0.028 (1)0.0151 (8)0.0043 (8)0.0099 (8)
O30.040 (1)0.056 (1)0.028 (1)0.0230 (10)0.0079 (9)0.0111 (10)
O40.0248 (9)0.0275 (9)0.031 (1)0.0026 (7)0.0018 (8)0.0035 (8)
C10.042 (2)0.038 (2)0.022 (2)0.017 (1)0.004 (1)0.000 (1)
C20.044 (2)0.039 (2)0.021 (2)0.021 (1)0.002 (1)0.001 (1)
C30.042 (2)0.044 (2)0.021 (2)0.019 (1)0.001 (1)0.000 (1)
C40.040 (2)0.044 (2)0.022 (2)0.019 (1)0.003 (1)0.008 (1)
C50.045 (2)0.042 (2)0.025 (2)0.024 (1)0.008 (1)0.010 (1)
C60.053 (2)0.034 (1)0.018 (2)0.020 (1)0.005 (1)0.005 (1)
C70.048 (2)0.040 (2)0.018 (2)0.017 (1)0.003 (1)0.003 (1)
C80.039 (2)0.051 (2)0.027 (2)0.020 (1)0.000 (1)0.009 (1)
C90.044 (2)0.047 (2)0.029 (2)0.011 (1)0.006 (1)0.005 (1)
C100.043 (2)0.066 (2)0.033 (2)0.024 (2)0.001 (1)0.007 (2)
C110.041 (2)0.058 (2)0.048 (2)0.014 (2)0.005 (2)0.016 (2)
C120.059 (2)0.035 (2)0.024 (2)0.018 (1)0.008 (1)0.001 (1)
C130.105 (3)0.064 (3)0.041 (2)0.053 (2)0.008 (2)0.013 (2)
C140.069 (2)0.047 (2)0.028 (2)0.011 (2)0.003 (2)0.001 (1)
C150.098 (3)0.043 (2)0.051 (3)0.002 (2)0.025 (2)0.012 (2)
Geometric parameters (Å, º) top
Zn1—O12.237 (2)C10—H110.950
Zn1—O1i2.237 (2)C10—H120.950
Zn1—O22.070 (2)C11—H40.950
Zn1—O2i2.070 (2)C11—H50.950
Zn1—O42.034 (2)C11—H60.950
Zn1—O4i2.034 (2)C12—C131.536 (4)
O1—C11.264 (3)C12—C141.532 (4)
O2—C11.280 (3)C12—C151.524 (5)
O3—C31.348 (4)C13—H190.950
O3—H10.909C13—H200.950
O4—C161.469 (6)C13—H210.950
O4—C181.458 (6)C14—H130.950
C1—C21.490 (4)C14—H140.950
C2—C31.417 (4)C14—H150.950
C2—C71.380 (4)C15—H160.950
C3—C41.418 (4)C15—H170.950
C4—C51.387 (4)C15—H180.950
C4—C81.544 (4)C16—C171.503 (8)
C5—C61.398 (4)C16—H220.953
C5—H30.950C16—H230.979
C6—C71.384 (4)C17—H240.950
C6—C121.536 (4)C17—H250.950
C7—H20.950C17—H260.950
C8—C91.542 (4)C18—C191.507 (9)
C8—C101.533 (4)C18—H270.967
C8—C111.522 (5)C18—H280.943
C9—H70.950C19—H290.950
C9—H80.950C19—H300.950
C9—H90.950C19—H310.950
C10—H100.950
O1···O4ii2.625 (3)O3···C17iv3.455 (6)
O1···C18ii3.204 (7)O3···C2iv3.488 (4)
O1···C19ii3.337 (7)O4···C7ii3.569 (3)
O1···O1ii3.364 (4)C1···C17iv3.434 (7)
O1···O2iii3.395 (3)C2···C17iv3.399 (7)
O2···C7iv3.529 (3)C3···C17iv3.404 (7)
O2···C17iv3.531 (6)C15···C19v3.578 (8)
O3···C7iv3.355 (4)C19···C19vi3.10 (1)
O1—Zn1—O1i87.9 (1)C8—C11—H4109.5
O1—Zn1—O260.86 (7)C8—C11—H5109.5
O1—Zn1—O2i100.27 (8)C8—C11—H6109.5
O1—Zn1—O494.01 (7)H4—C11—H5109.5
O1—Zn1—O4i151.28 (7)H4—C11—H6109.5
O1i—Zn1—O2100.27 (8)H5—C11—H6109.5
O1i—Zn1—O2i60.86 (7)C6—C12—C13112.4 (3)
O1i—Zn1—O4151.28 (7)C6—C12—C14108.5 (2)
O1i—Zn1—O4i94.01 (7)C6—C12—C15110.3 (2)
O2—Zn1—O2i155.2 (1)C13—C12—C14108.0 (3)
O2—Zn1—O4105.68 (7)C13—C12—C15108.1 (3)
O2—Zn1—O4i90.67 (7)C14—C12—C15109.4 (3)
O2i—Zn1—O490.67 (7)C12—C13—H19109.5
O2i—Zn1—O4i105.68 (7)C12—C13—H20109.5
O4—Zn1—O4i97.7 (1)C12—C13—H21109.5
Zn1—O1—C186.7 (2)H19—C13—H20109.5
Zn1—O2—C193.9 (2)H19—C13—H21109.5
C3—O3—H1102.6H20—C13—H21109.5
Zn1—O4—C16119.2 (3)C12—C14—H13109.5
Zn1—O4—C18126.7 (3)C12—C14—H14109.5
O1—C1—O2118.5 (2)C12—C14—H15109.5
O1—C1—C2121.7 (3)H13—C14—H14109.5
O2—C1—C2119.9 (3)H13—C14—H15109.5
C1—C2—C3120.3 (3)H14—C14—H15109.5
C1—C2—C7119.5 (3)C12—C15—H16109.5
C3—C2—C7120.2 (2)C12—C15—H17109.5
O3—C3—C2121.9 (2)C12—C15—H18109.5
O3—C3—C4118.8 (3)H16—C15—H17109.5
C2—C3—C4119.3 (3)H16—C15—H18109.5
C3—C4—C5117.4 (3)H17—C15—H18109.5
C3—C4—C8120.5 (3)O4—C16—C17110.0 (5)
C5—C4—C8122.2 (2)O4—C16—H22112.2
C4—C5—C6124.3 (3)O4—C16—H23110.5
C4—C5—H3117.8C17—C16—H22109.3
C6—C5—H3117.9C17—C16—H23107.9
C5—C6—C7116.8 (3)C18—C16—H22102.2
C5—C6—C12122.6 (3)C18—C16—H27108.8
C7—C6—C12120.5 (3)C19—C16—H27106.7
C2—C7—C6122.1 (3)H22—C16—H23106.8
C2—C7—H2118.9C16—C17—H24109.5
C6—C7—H2119.0C16—C17—H25109.5
C4—C8—C9109.6 (2)C16—C17—H26109.5
C4—C8—C10111.2 (3)H24—C17—H25109.5
C4—C8—C11110.8 (2)H24—C17—H26109.5
C9—C8—C10107.2 (2)H25—C17—H26109.5
C9—C8—C11110.5 (3)O4—C18—C19111.9 (5)
C10—C8—C11107.5 (3)O4—C18—H27108.0
C8—C9—H7109.5O4—C18—H28109.4
C8—C9—H8109.5C19—C18—H27108.7
C8—C9—H9109.5C19—C18—H28110.2
H7—C9—H8109.5H27—C18—H28108.6
H7—C9—H9109.5C16—C19—H29109.5
H8—C9—H9109.5C16—C19—H30109.5
C8—C10—H10109.5C16—C19—H31109.5
C8—C10—H11109.5C18—C19—H30126.9
C8—C10—H12109.5C18—C19—H31106.5
H10—C10—H11109.5H29—C19—H30109.5
H10—C10—H12109.5H29—C19—H31109.5
H11—C10—H12109.5H30—C19—H31109.5
Symmetry codes: (i) x, y, z+1/2; (ii) x, y+2, z+1; (iii) x, y+2, z+1/2; (iv) x, y+2, z1/2; (v) x, y+1, z; (vi) x, y, z+3/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H1···O20.911.722.573 (3)156
 

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