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
CCDC reference: 225691
Key indicators
- Single-crystal X-ray study
- T = 93 K
- Mean (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
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.
Crystal data top
[Zn(C15H21O3)2(C2H6O)2] | F(000) = 1408 |
Mr = 656.18 | Dx = 1.213 Mg m−3 |
Monoclinic, C2/c | Cu Kα radiation, λ = 1.5418 Å |
Hall symbol: -C 2yc | Cell parameters from 15255 reflections |
a = 33.891 (4) Å | θ = 4.2–68.1° |
b = 11.191 (1) Å | µ = 1.32 mm−1 |
c = 9.491 (1) Å | T = 93 K |
β = 93.75 (1)° | Needle, colourless |
V = 3592.1 (7) Å3 | 0.45 × 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-1 | Rint = 0.040 |
48 frames, delta ω = 15 deg scans | θmax = 68.2° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −40→40 |
Tmin = 0.548, Tmax = 0.877 | k = −13→13 |
16078 measured reflections | l = −9→9 |
3054 independent reflections | |
Refinement top
Refinement on F2 | H-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 = 1.65 | Δρmax = 0.37 e Å−3 |
3054 reflections | Δρmin = −0.25 e Å−3 |
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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
Zn1 | 0.0000 | 0.92382 (4) | 0.2500 | 0.0245 (1) | |
O1 | 0.02843 (6) | 1.0677 (2) | 0.3851 (2) | 0.0344 (6) | |
O2 | 0.05906 (5) | 0.9635 (2) | 0.2309 (2) | 0.0332 (6) | |
O3 | 0.12961 (6) | 1.0184 (2) | 0.1691 (2) | 0.0409 (6) | |
O4 | −0.00098 (5) | 0.8043 (2) | 0.4112 (2) | 0.0280 (5) | |
C1 | 0.05959 (9) | 1.0472 (3) | 0.3229 (3) | 0.0337 (8) | |
C2 | 0.09628 (9) | 1.1185 (3) | 0.3532 (3) | 0.0349 (8) | |
C3 | 0.12952 (9) | 1.1009 (3) | 0.2724 (3) | 0.0358 (9) | |
C4 | 0.16369 (9) | 1.1724 (3) | 0.3002 (3) | 0.0357 (8) | |
C5 | 0.16261 (9) | 1.2567 (3) | 0.4070 (3) | 0.0376 (9) | |
C6 | 0.13006 (9) | 1.2762 (3) | 0.4872 (3) | 0.0354 (8) | |
C7 | 0.09714 (9) | 1.2054 (3) | 0.4566 (3) | 0.0354 (8) | |
C8 | 0.20034 (9) | 1.1553 (3) | 0.2139 (3) | 0.0388 (9) | |
C9 | 0.18932 (9) | 1.1828 (3) | 0.0570 (3) | 0.0398 (9) | |
C10 | 0.23363 (9) | 1.2415 (3) | 0.2632 (4) | 0.048 (1) | |
C11 | 0.21647 (9) | 1.0288 (3) | 0.2309 (4) | 0.049 (1) | |
C12 | 0.13065 (10) | 1.3671 (3) | 0.6085 (3) | 0.0397 (9) | |
C13 | 0.1656 (1) | 1.4541 (4) | 0.6059 (4) | 0.070 (1) | |
C14 | 0.1344 (1) | 1.2990 (3) | 0.7487 (3) | 0.048 (1) | |
C15 | 0.0926 (1) | 1.4401 (3) | 0.6003 (4) | 0.065 (1) | |
C16 | 0.0317 (2) | 0.7186 (6) | 0.4332 (8) | 0.033 (1)* | 0.50 |
C17 | 0.0634 (2) | 0.7698 (5) | 0.5338 (7) | 0.037 (1)* | 0.50 |
C18 | 0.0332 (2) | 0.7505 (6) | 0.4883 (8) | 0.037 (2)* | 0.50 |
C19 | 0.0213 (2) | 0.6751 (6) | 0.6102 (8) | 0.049 (2)* | 0.50 |
H1 | 0.1057 | 0.9824 | 0.1745 | 0.0514* | |
H2 | 0.0744 | 1.2169 | 0.5085 | 0.0425* | |
H3 | 0.1855 | 1.3044 | 0.4270 | 0.0451* | |
H4 | 0.2246 | 1.0150 | 0.3272 | 0.0586* | |
H5 | 0.1964 | 0.9732 | 0.2014 | 0.0586* | |
H6 | 0.2384 | 1.0194 | 0.1746 | 0.0586* | |
H7 | 0.1686 | 1.1312 | 0.0230 | 0.0478* | |
H8 | 0.2118 | 1.1707 | 0.0038 | 0.0478* | |
H9 | 0.1808 | 1.2635 | 0.0476 | 0.0478* | |
H10 | 0.2412 | 1.2268 | 0.3597 | 0.0571* | |
H11 | 0.2557 | 1.2294 | 0.2080 | 0.0571* | |
H12 | 0.2246 | 1.3215 | 0.2522 | 0.0571* | |
H13 | 0.1123 | 1.2474 | 0.7545 | 0.0581* | |
H14 | 0.1580 | 1.2532 | 0.7538 | 0.0581* | |
H15 | 0.1351 | 1.3543 | 0.8248 | 0.0581* | |
H16 | 0.0706 | 1.3881 | 0.6068 | 0.0785* | |
H17 | 0.0902 | 1.4818 | 0.5130 | 0.0785* | |
H18 | 0.0933 | 1.4958 | 0.6759 | 0.0785* | |
H19 | 0.1651 | 1.5076 | 0.6835 | 0.0836* | |
H20 | 0.1897 | 1.4104 | 0.6126 | 0.0836* | |
H21 | 0.1638 | 1.4981 | 0.5202 | 0.0836* | |
H22 | 0.0231 | 0.6440 | 0.4689 | 0.0400* | 0.50 |
H23 | 0.0435 | 0.7016 | 0.3440 | 0.0400* | 0.50 |
H24 | 0.0845 | 0.7143 | 0.5464 | 0.0444* | 0.50 |
H25 | 0.0728 | 0.8422 | 0.4964 | 0.0444* | 0.50 |
H26 | 0.0527 | 0.7851 | 0.6222 | 0.0444* | 0.50 |
H27 | 0.0464 | 0.7001 | 0.4235 | 0.0438* | 0.50 |
H28 | 0.0508 | 0.8112 | 0.5210 | 0.0438* | 0.50 |
H29 | 0.0103 | 0.7410 | 0.6570 | 0.0584* | 0.50 |
H30 | 0.0031 | 0.6106 | 0.6062 | 0.0584* | 0.50 |
H31 | 0.0451 | 0.6510 | 0.6605 | 0.0584* | 0.50 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Zn1 | 0.0231 (3) | 0.0225 (3) | 0.0282 (3) | 0.0000 | 0.0042 (2) | 0.0000 |
O1 | 0.041 (1) | 0.039 (1) | 0.024 (1) | −0.0175 (9) | 0.0096 (8) | −0.0073 (9) |
O2 | 0.0318 (10) | 0.040 (1) | 0.028 (1) | −0.0151 (8) | 0.0043 (8) | −0.0099 (8) |
O3 | 0.040 (1) | 0.056 (1) | 0.028 (1) | −0.0230 (10) | 0.0079 (9) | −0.0111 (10) |
O4 | 0.0248 (9) | 0.0275 (9) | 0.031 (1) | 0.0026 (7) | −0.0018 (8) | 0.0035 (8) |
C1 | 0.042 (2) | 0.038 (2) | 0.022 (2) | −0.017 (1) | 0.004 (1) | 0.000 (1) |
C2 | 0.044 (2) | 0.039 (2) | 0.021 (2) | −0.021 (1) | 0.002 (1) | −0.001 (1) |
C3 | 0.042 (2) | 0.044 (2) | 0.021 (2) | −0.019 (1) | 0.001 (1) | 0.000 (1) |
C4 | 0.040 (2) | 0.044 (2) | 0.022 (2) | −0.019 (1) | −0.003 (1) | 0.008 (1) |
C5 | 0.045 (2) | 0.042 (2) | 0.025 (2) | −0.024 (1) | −0.008 (1) | 0.010 (1) |
C6 | 0.053 (2) | 0.034 (1) | 0.018 (2) | −0.020 (1) | −0.005 (1) | 0.005 (1) |
C7 | 0.048 (2) | 0.040 (2) | 0.018 (2) | −0.017 (1) | 0.003 (1) | 0.003 (1) |
C8 | 0.039 (2) | 0.051 (2) | 0.027 (2) | −0.020 (1) | 0.000 (1) | 0.009 (1) |
C9 | 0.044 (2) | 0.047 (2) | 0.029 (2) | −0.011 (1) | 0.006 (1) | 0.005 (1) |
C10 | 0.043 (2) | 0.066 (2) | 0.033 (2) | −0.024 (2) | 0.001 (1) | 0.007 (2) |
C11 | 0.041 (2) | 0.058 (2) | 0.048 (2) | −0.014 (2) | 0.005 (2) | 0.016 (2) |
C12 | 0.059 (2) | 0.035 (2) | 0.024 (2) | −0.018 (1) | −0.008 (1) | 0.001 (1) |
C13 | 0.105 (3) | 0.064 (3) | 0.041 (2) | −0.053 (2) | 0.008 (2) | −0.013 (2) |
C14 | 0.069 (2) | 0.047 (2) | 0.028 (2) | −0.011 (2) | −0.003 (2) | −0.001 (1) |
C15 | 0.098 (3) | 0.043 (2) | 0.051 (3) | −0.002 (2) | −0.025 (2) | −0.012 (2) |
Geometric parameters (Å, º) top
Zn1—O1 | 2.237 (2) | C10—H11 | 0.950 |
Zn1—O1i | 2.237 (2) | C10—H12 | 0.950 |
Zn1—O2 | 2.070 (2) | C11—H4 | 0.950 |
Zn1—O2i | 2.070 (2) | C11—H5 | 0.950 |
Zn1—O4 | 2.034 (2) | C11—H6 | 0.950 |
Zn1—O4i | 2.034 (2) | C12—C13 | 1.536 (4) |
O1—C1 | 1.264 (3) | C12—C14 | 1.532 (4) |
O2—C1 | 1.280 (3) | C12—C15 | 1.524 (5) |
O3—C3 | 1.348 (4) | C13—H19 | 0.950 |
O3—H1 | 0.909 | C13—H20 | 0.950 |
O4—C16 | 1.469 (6) | C13—H21 | 0.950 |
O4—C18 | 1.458 (6) | C14—H13 | 0.950 |
C1—C2 | 1.490 (4) | C14—H14 | 0.950 |
C2—C3 | 1.417 (4) | C14—H15 | 0.950 |
C2—C7 | 1.380 (4) | C15—H16 | 0.950 |
C3—C4 | 1.418 (4) | C15—H17 | 0.950 |
C4—C5 | 1.387 (4) | C15—H18 | 0.950 |
C4—C8 | 1.544 (4) | C16—C17 | 1.503 (8) |
C5—C6 | 1.398 (4) | C16—H22 | 0.953 |
C5—H3 | 0.950 | C16—H23 | 0.979 |
C6—C7 | 1.384 (4) | C17—H24 | 0.950 |
C6—C12 | 1.536 (4) | C17—H25 | 0.950 |
C7—H2 | 0.950 | C17—H26 | 0.950 |
C8—C9 | 1.542 (4) | C18—C19 | 1.507 (9) |
C8—C10 | 1.533 (4) | C18—H27 | 0.967 |
C8—C11 | 1.522 (5) | C18—H28 | 0.943 |
C9—H7 | 0.950 | C19—H29 | 0.950 |
C9—H8 | 0.950 | C19—H30 | 0.950 |
C9—H9 | 0.950 | C19—H31 | 0.950 |
C10—H10 | 0.950 | | |
| | | |
O1···O4ii | 2.625 (3) | O3···C17iv | 3.455 (6) |
O1···C18ii | 3.204 (7) | O3···C2iv | 3.488 (4) |
O1···C19ii | 3.337 (7) | O4···C7ii | 3.569 (3) |
O1···O1ii | 3.364 (4) | C1···C17iv | 3.434 (7) |
O1···O2iii | 3.395 (3) | C2···C17iv | 3.399 (7) |
O2···C7iv | 3.529 (3) | C3···C17iv | 3.404 (7) |
O2···C17iv | 3.531 (6) | C15···C19v | 3.578 (8) |
O3···C7iv | 3.355 (4) | C19···C19vi | 3.10 (1) |
| | | |
O1—Zn1—O1i | 87.9 (1) | C8—C11—H4 | 109.5 |
O1—Zn1—O2 | 60.86 (7) | C8—C11—H5 | 109.5 |
O1—Zn1—O2i | 100.27 (8) | C8—C11—H6 | 109.5 |
O1—Zn1—O4 | 94.01 (7) | H4—C11—H5 | 109.5 |
O1—Zn1—O4i | 151.28 (7) | H4—C11—H6 | 109.5 |
O1i—Zn1—O2 | 100.27 (8) | H5—C11—H6 | 109.5 |
O1i—Zn1—O2i | 60.86 (7) | C6—C12—C13 | 112.4 (3) |
O1i—Zn1—O4 | 151.28 (7) | C6—C12—C14 | 108.5 (2) |
O1i—Zn1—O4i | 94.01 (7) | C6—C12—C15 | 110.3 (2) |
O2—Zn1—O2i | 155.2 (1) | C13—C12—C14 | 108.0 (3) |
O2—Zn1—O4 | 105.68 (7) | C13—C12—C15 | 108.1 (3) |
O2—Zn1—O4i | 90.67 (7) | C14—C12—C15 | 109.4 (3) |
O2i—Zn1—O4 | 90.67 (7) | C12—C13—H19 | 109.5 |
O2i—Zn1—O4i | 105.68 (7) | C12—C13—H20 | 109.5 |
O4—Zn1—O4i | 97.7 (1) | C12—C13—H21 | 109.5 |
Zn1—O1—C1 | 86.7 (2) | H19—C13—H20 | 109.5 |
Zn1—O2—C1 | 93.9 (2) | H19—C13—H21 | 109.5 |
C3—O3—H1 | 102.6 | H20—C13—H21 | 109.5 |
Zn1—O4—C16 | 119.2 (3) | C12—C14—H13 | 109.5 |
Zn1—O4—C18 | 126.7 (3) | C12—C14—H14 | 109.5 |
O1—C1—O2 | 118.5 (2) | C12—C14—H15 | 109.5 |
O1—C1—C2 | 121.7 (3) | H13—C14—H14 | 109.5 |
O2—C1—C2 | 119.9 (3) | H13—C14—H15 | 109.5 |
C1—C2—C3 | 120.3 (3) | H14—C14—H15 | 109.5 |
C1—C2—C7 | 119.5 (3) | C12—C15—H16 | 109.5 |
C3—C2—C7 | 120.2 (2) | C12—C15—H17 | 109.5 |
O3—C3—C2 | 121.9 (2) | C12—C15—H18 | 109.5 |
O3—C3—C4 | 118.8 (3) | H16—C15—H17 | 109.5 |
C2—C3—C4 | 119.3 (3) | H16—C15—H18 | 109.5 |
C3—C4—C5 | 117.4 (3) | H17—C15—H18 | 109.5 |
C3—C4—C8 | 120.5 (3) | O4—C16—C17 | 110.0 (5) |
C5—C4—C8 | 122.2 (2) | O4—C16—H22 | 112.2 |
C4—C5—C6 | 124.3 (3) | O4—C16—H23 | 110.5 |
C4—C5—H3 | 117.8 | C17—C16—H22 | 109.3 |
C6—C5—H3 | 117.9 | C17—C16—H23 | 107.9 |
C5—C6—C7 | 116.8 (3) | C18—C16—H22 | 102.2 |
C5—C6—C12 | 122.6 (3) | C18—C16—H27 | 108.8 |
C7—C6—C12 | 120.5 (3) | C19—C16—H27 | 106.7 |
C2—C7—C6 | 122.1 (3) | H22—C16—H23 | 106.8 |
C2—C7—H2 | 118.9 | C16—C17—H24 | 109.5 |
C6—C7—H2 | 119.0 | C16—C17—H25 | 109.5 |
C4—C8—C9 | 109.6 (2) | C16—C17—H26 | 109.5 |
C4—C8—C10 | 111.2 (3) | H24—C17—H25 | 109.5 |
C4—C8—C11 | 110.8 (2) | H24—C17—H26 | 109.5 |
C9—C8—C10 | 107.2 (2) | H25—C17—H26 | 109.5 |
C9—C8—C11 | 110.5 (3) | O4—C18—C19 | 111.9 (5) |
C10—C8—C11 | 107.5 (3) | O4—C18—H27 | 108.0 |
C8—C9—H7 | 109.5 | O4—C18—H28 | 109.4 |
C8—C9—H8 | 109.5 | C19—C18—H27 | 108.7 |
C8—C9—H9 | 109.5 | C19—C18—H28 | 110.2 |
H7—C9—H8 | 109.5 | H27—C18—H28 | 108.6 |
H7—C9—H9 | 109.5 | C16—C19—H29 | 109.5 |
H8—C9—H9 | 109.5 | C16—C19—H30 | 109.5 |
C8—C10—H10 | 109.5 | C16—C19—H31 | 109.5 |
C8—C10—H11 | 109.5 | C18—C19—H30 | 126.9 |
C8—C10—H12 | 109.5 | C18—C19—H31 | 106.5 |
H10—C10—H11 | 109.5 | H29—C19—H30 | 109.5 |
H10—C10—H12 | 109.5 | H29—C19—H31 | 109.5 |
H11—C10—H12 | 109.5 | H30—C19—H31 | 109.5 |
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, z−1/2; (v) x, y+1, z; (vi) −x, y, −z+3/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H1···O2 | 0.91 | 1.72 | 2.573 (3) | 156 |