The title compound, [Zn(C15H21O3)2(C3H6OS)2], is a powerful charge-control agent used widely for toners in electrophotography. This ZnII complex has no molecular symmetry and possesses a deformed tetrahedral coordination geometry. Two 3,5-di-tert-butyl-2-hydroxybenzoate ligands serve as monodentate ligands, while two dimethyl sulfoxide molecules are coordinated to the Zn atom.
Supporting information
CCDC reference: 270499
Key indicators
- Single-crystal X-ray study
- T = 93 K
- Mean (C-C) = 0.018 Å
- Disorder in main residue
- R factor = 0.058
- wR factor = 0.170
- Data-to-parameter ratio = 15.4
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT026_ALERT_3_A Ratio Observed / Unique Reflections too Low .... 15 Perc.
| Author Response: The single crystal used for analysis was extremely small
(0.1x0.08x0.02 mm3). In spite of the long-time exposure, the ratio could not
be improved.
|
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.88
| Author Response: A two-dimentional detector (IP) was used in combination with
Cu-target as radation.
|
Alert level B
GOODF01_ALERT_2_B The least squares goodness of fit parameter lies
outside the range 0.60 <> 4.00
Goodness of fit given = 0.472
REFLT03_ALERT_3_B Reflection count < 90% complete (theta max?)
From the CIF: _diffrn_reflns_theta_max 68.20
From the CIF: _diffrn_reflns_theta_full 68.20
From the CIF: _reflns_number_total 6152
TEST2: Reflns within _diffrn_reflns_theta_max
Count of symmetry unique reflns 7029
Completeness (_total/calc) 87.52%
RINTA01_ALERT_3_B The value of Rint is greater than 0.15
Rint given 0.175
PLAT020_ALERT_3_B The value of Rint is greater than 0.10 ......... 0.17
PLAT022_ALERT_3_B Ratio Unique / Expected Reflections too Low .... 0.88
PLAT201_ALERT_2_B Isotropic non-H Atoms in Main Residue(s) ....... 7
PLAT341_ALERT_3_B Low Bond Precision on C-C bonds (x 1000) Ang ... 18
Alert level C
CHEMW01_ALERT_1_C The difference between the given and expected weight for
compound is greater 1 mass unit. Check that all hydrogen
atoms have been taken into account.
PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 1.20
PLAT086_ALERT_2_C Unsatisfactory S Value (Too Low or Not Given) .. 0.47
PLAT128_ALERT_4_C Non-standard setting of Space group P21/c .... P21/a
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O3
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C1
PLAT301_ALERT_3_C Main Residue Disorder ......................... 13.00 Perc.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond C3 - C4 ... 1.38 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 19
Alert level G
ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be
replaced by the scaled T values. Since the ratio of scaled T's
is identical to the ratio of reported T values, the scaling
does not imply a change to the absorption corrections used in
the study.
Ratio of Tmax expected/reported 1.199
Tmax scaled 0.956 Tmin scaled 0.743
REFLT03_ALERT_1_G ALERT: Expected hkl max differ from CIF values
From the CIF: _diffrn_reflns_theta_max 68.20
From the CIF: _reflns_number_total 6152
From the CIF: _diffrn_reflns_limit_ max hkl 17. 15. 21.
From the CIF: _diffrn_reflns_limit_ min hkl -17. -15. -23.
TEST1: Expected hkl limits for theta max
Calculated maximum hkl 20. 15. 23.
Calculated minimum hkl -20. -15. -23.
2 ALERT level A = In general: serious problem
7 ALERT level B = Potentially serious problem
9 ALERT level C = Check and explain
2 ALERT level G = General alerts; check
2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
6 ALERT type 2 Indicator that the structure model may be wrong or deficient
9 ALERT type 3 Indicator that the structure quality may be low
3 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.
Bis[3,5-di-
tert-butyl-2-hydroxybenzoato-
κO]bis(dimethyl
sulfoxide-
κO)zinc(II)
top
Crystal data top
[Zn(C15H21O3)2(C2H6OS)2] | F(000) = 1536.0 |
Mr = 718.29 | Dx = 1.245 Mg m−3 |
Monoclinic, P21/a | Cu Kα radiation, λ = 1.5418 Å |
Hall symbol: -P 2yab | Cell parameters from 11185 reflections |
a = 16.688 (4) Å | θ = 3.0–67.9° |
b = 12.946 (3) Å | µ = 2.27 mm−1 |
c = 19.178 (4) Å | T = 93 K |
β = 111.97 (2)° | Platelet, colourless |
V = 3842.4 (16) Å3 | 0.10 × 0.08 × 0.02 mm |
Z = 4 | |
Data collection top
Rigaku R-AXIS RAPID imaging plate diffractometer | 944 reflections with F2 > 2σ(F2) |
Detector resolution: 10.00 pixels mm-1 | Rint = 0.175 |
48 frames, Δ ω = 15° scans | θmax = 68.2° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −17→17 |
Tmin = 0.743, Tmax = 0.956 | k = −15→15 |
24925 measured reflections | l = −23→21 |
6152 independent reflections | |
Refinement top
Refinement on F2 | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.058 | w = 1/{[σ2(Fo2) + 2Fc2)/3]2} |
wR(F2) = 0.170 | (Δ/σ)max = 0.003 |
S = 0.47 | Δρmax = 0.62 e Å−3 |
6152 reflections | Δρmin = −0.40 e Å−3 |
399 parameters | |
Special details top
Refinement. Refinement using reflections with F2 > -10.0 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 | 0.08349 (9) | 0.2444 (1) | 0.50940 (8) | 0.0588 (5) | |
S1 | −0.0444 (2) | 0.1178 (3) | 0.5560 (2) | 0.069 (1) | |
S2 | 0.1481 (2) | 0.4590 (2) | 0.5567 (2) | 0.063 (1) | |
O1 | 0.1604 (6) | 0.2541 (9) | 0.7952 (5) | 0.048 (3)* | 0.65 |
O1A | 0.315 (1) | 0.105 (1) | 0.667 (1) | 0.044 (4)* | 0.35 |
O2 | 0.1046 (5) | 0.2648 (6) | 0.6576 (4) | 0.068 (3) | |
O3 | 0.1777 (5) | 0.1848 (6) | 0.5954 (4) | 0.073 (3) | |
O4 | 0.0747 (5) | 0.0729 (6) | 0.3068 (4) | 0.067 (3) | |
O5 | 0.2008 (4) | 0.3036 (6) | 0.4539 (4) | 0.068 (3) | |
O6 | 0.0913 (5) | 0.1929 (5) | 0.4147 (4) | 0.059 (3) | |
O7 | 0.0676 (5) | 0.3959 (5) | 0.5109 (4) | 0.061 (3) | |
O8 | −0.0334 (4) | 0.1929 (5) | 0.4984 (4) | 0.064 (3) | |
C1 | 0.1661 (7) | 0.2093 (9) | 0.6562 (7) | 0.050 (4) | |
C2 | 0.2370 (8) | 0.1765 (8) | 0.7283 (7) | 0.056 (4) | |
C3 | 0.3088 (8) | 0.1187 (8) | 0.7283 (7) | 0.048 (4) | |
C4 | 0.3731 (9) | 0.0846 (10) | 0.7935 (7) | 0.062 (5) | |
C5 | 0.3614 (7) | 0.1073 (9) | 0.8618 (7) | 0.064 (4) | |
C6 | 0.2902 (8) | 0.1625 (8) | 0.8666 (7) | 0.058 (4) | |
C7 | 0.2267 (7) | 0.1961 (8) | 0.7982 (7) | 0.057 (4) | |
C8 | 0.4539 (9) | 0.023 (1) | 0.7987 (7) | 0.087 (6) | |
C9 | 0.449 (1) | −0.091 (1) | 0.8305 (9) | 0.059 (4)* | 0.65 |
C9A | 0.430 (3) | −0.056 (4) | 0.740 (3) | 0.114 (2)* | 0.35 |
C10 | 0.536 (1) | 0.077 (2) | 0.838 (1) | 0.088 (4)* | 0.65 |
C10A | 0.526 (2) | 0.038 (3) | 0.883 (2) | 0.076 (3)* | 0.35 |
C11 | 0.451 (1) | −0.001 (2) | 0.715 (1) | 0.085 (4)* | 0.65 |
C11A | 0.502 (2) | 0.106 (3) | 0.760 (2) | 0.073 (3)* | 0.35 |
C12 | 0.2772 (9) | 0.183 (1) | 0.9436 (6) | 0.085 (5) | |
C13 | 0.355 (1) | 0.133 (2) | 1.007 (1) | 0.085 (4)* | 0.65 |
C13A | 0.279 (2) | 0.082 (3) | 0.986 (2) | 0.076 (3)* | 0.35 |
C14 | 0.283 (1) | 0.304 (2) | 0.955 (1) | 0.073 (4)* | 0.65 |
C14A | 0.357 (2) | 0.237 (3) | 1.001 (2) | 0.078 (3)* | 0.35 |
C15 | 0.190 (1) | 0.137 (1) | 0.9390 (10) | 0.075 (4)* | 0.65 |
C15A | 0.191 (2) | 0.247 (3) | 0.934 (2) | 0.075 (3)* | 0.35 |
C16 | 0.1566 (8) | 0.241 (1) | 0.4074 (6) | 0.057 (4) | |
C17 | 0.1768 (7) | 0.2115 (9) | 0.3404 (7) | 0.060 (5) | |
C18 | 0.2383 (7) | 0.2704 (9) | 0.3266 (5) | 0.051 (4) | |
C19 | 0.2578 (7) | 0.255 (1) | 0.2628 (6) | 0.056 (4) | |
C20 | 0.2135 (8) | 0.174 (1) | 0.2139 (7) | 0.064 (5) | |
C21 | 0.1509 (9) | 0.1125 (10) | 0.2235 (7) | 0.062 (5) | |
C22 | 0.1332 (7) | 0.1328 (9) | 0.2911 (7) | 0.055 (5) | |
C23 | 0.3254 (8) | 0.3134 (10) | 0.2417 (7) | 0.061 (5) | |
C24 | 0.3661 (8) | 0.4003 (10) | 0.2979 (7) | 0.077 (5) | |
C25 | 0.3972 (7) | 0.2442 (10) | 0.2419 (5) | 0.067 (4) | |
C26 | 0.2827 (7) | 0.3662 (9) | 0.1662 (8) | 0.080 (5) | |
C27 | 0.1017 (9) | 0.026 (1) | 0.1693 (7) | 0.069 (5) | |
C28 | 0.0052 (9) | 0.044 (1) | 0.1397 (7) | 0.093 (6) | |
C29 | 0.1278 (10) | −0.081 (1) | 0.2049 (7) | 0.098 (6) | |
C30 | 0.1267 (8) | 0.0306 (9) | 0.0989 (7) | 0.090 (5) | |
C31 | −0.0988 (7) | 0.1885 (9) | 0.6056 (6) | 0.076 (5) | |
C32 | −0.1322 (7) | 0.0389 (8) | 0.5015 (7) | 0.069 (5) | |
C33 | 0.1177 (7) | 0.5225 (8) | 0.6260 (6) | 0.066 (4) | |
C34 | 0.1434 (7) | 0.5670 (9) | 0.4969 (6) | 0.069 (5) | |
H3 | 0.3129 | 0.1026 | 0.6814 | 0.0575* | 0.65 |
H5 | 0.4043 | 0.0838 | 0.9074 | 0.0773* | |
H7 | 0.1770 | 0.2317 | 0.7984 | 0.0679* | 0.35 |
H9a | 0.3972 | −0.1240 | 0.7992 | 0.0706* | 0.65 |
H9b | 0.4973 | −0.1307 | 0.8305 | 0.0706* | 0.65 |
H9c | 0.4504 | −0.0865 | 0.8803 | 0.0706* | 0.65 |
H10a | 0.5829 | 0.0336 | 0.8398 | 0.1053* | 0.65 |
H10b | 0.5379 | 0.1387 | 0.8113 | 0.1053* | 0.65 |
H10c | 0.5412 | 0.0941 | 0.8874 | 0.1053* | 0.65 |
H11a | 0.3990 | −0.0359 | 0.6864 | 0.1021* | 0.65 |
H11b | 0.4547 | 0.0614 | 0.6902 | 0.1021* | 0.65 |
H11c | 0.4990 | −0.0442 | 0.7181 | 0.1021* | 0.65 |
H13a | 0.3565 | 0.0608 | 0.9973 | 0.1021* | 0.65 |
H13b | 0.4073 | 0.1636 | 1.0076 | 0.1021* | 0.65 |
H13c | 0.3500 | 0.1429 | 1.0538 | 0.1021* | 0.65 |
H14a | 0.3375 | 0.3278 | 0.9575 | 0.0874* | 0.65 |
H14b | 0.2385 | 0.3362 | 0.9141 | 0.0874* | 0.65 |
H14c | 0.2754 | 0.3207 | 1.0006 | 0.0874* | 0.65 |
H15a | 0.1827 | 0.1490 | 0.9851 | 0.0898* | 0.65 |
H15b | 0.1445 | 0.1693 | 0.8991 | 0.0898* | 0.65 |
H15c | 0.1896 | 0.0650 | 0.9298 | 0.0898* | 0.65 |
H9Aa | 0.4002 | −0.1107 | 0.7533 | 0.1368* | 0.35 |
H9Ab | 0.3928 | −0.0268 | 0.6935 | 0.1368* | 0.35 |
H9Ac | 0.4802 | −0.0826 | 0.7345 | 0.1368* | 0.35 |
H10Aa | 0.5114 | −0.0045 | 0.9174 | 0.0914* | 0.35 |
H10Ab | 0.5813 | 0.0177 | 0.8840 | 0.0914* | 0.35 |
H10Ac | 0.5280 | 0.1079 | 0.8981 | 0.0914* | 0.35 |
H11Aa | 0.5494 | 0.0735 | 0.7538 | 0.0874* | 0.35 |
H11Ab | 0.4616 | 0.1286 | 0.7131 | 0.0874* | 0.35 |
H11Ac | 0.5219 | 0.1643 | 0.7928 | 0.0874* | 0.35 |
H13Aa | 0.2734 | 0.0978 | 1.0329 | 0.0911* | 0.35 |
H13Ab | 0.2320 | 0.0395 | 0.9571 | 0.0911* | 0.35 |
H13Ac | 0.3317 | 0.0473 | 0.9956 | 0.0911* | 0.35 |
H14Aa | 0.4067 | 0.1959 | 1.0091 | 0.0939* | 0.35 |
H14Ab | 0.3644 | 0.3024 | 0.9811 | 0.0939* | 0.35 |
H14Ac | 0.3488 | 0.2469 | 1.0466 | 0.0939* | 0.35 |
H15Aa | 0.1904 | 0.2625 | 0.9826 | 0.0905* | 0.35 |
H15Ab | 0.1894 | 0.3090 | 0.9078 | 0.0905* | 0.35 |
H15Ac | 0.1413 | 0.2063 | 0.9072 | 0.0905* | 0.35 |
H18 | 0.2680 | 0.3228 | 0.3614 | 0.0607* | |
H20 | 0.2282 | 0.1604 | 0.1714 | 0.0768* | |
H24a | 0.3919 | 0.3721 | 0.3470 | 0.0928* | |
H24b | 0.3227 | 0.4485 | 0.2968 | 0.0928* | |
H24c | 0.4089 | 0.4342 | 0.2848 | 0.0928* | |
H25a | 0.4386 | 0.2833 | 0.2302 | 0.0806* | |
H25b | 0.3746 | 0.1914 | 0.2053 | 0.0806* | |
H25c | 0.4238 | 0.2137 | 0.2902 | 0.0806* | |
H26a | 0.2404 | 0.4134 | 0.1688 | 0.0963* | |
H26b | 0.3251 | 0.4024 | 0.1539 | 0.0963* | |
H26c | 0.2560 | 0.3158 | 0.1287 | 0.0963* | |
H28a | −0.0081 | 0.1066 | 0.1117 | 0.1117* | |
H28b | −0.0136 | 0.0489 | 0.1807 | 0.1117* | |
H28c | −0.0234 | −0.0118 | 0.1081 | 0.1117* | |
H29a | 0.1877 | −0.0912 | 0.2164 | 0.1179* | |
H29b | 0.1162 | −0.0847 | 0.2497 | 0.1179* | |
H29c | 0.0955 | −0.1321 | 0.1706 | 0.1179* | |
H30a | 0.1097 | 0.0952 | 0.0744 | 0.1078* | |
H30b | 0.1874 | 0.0226 | 0.1140 | 0.1078* | |
H30c | 0.0981 | −0.0236 | 0.0654 | 0.1078* | |
H31a | −0.0644 | 0.2458 | 0.6304 | 0.0911* | |
H31b | −0.1529 | 0.2124 | 0.5710 | 0.0911* | |
H31c | −0.1079 | 0.1447 | 0.6417 | 0.0911* | |
H32a | −0.1820 | 0.0807 | 0.4783 | 0.0829* | |
H32b | −0.1437 | −0.0107 | 0.5330 | 0.0829* | |
H32c | −0.1181 | 0.0045 | 0.4638 | 0.0829* | |
H33a | 0.1641 | 0.5645 | 0.6568 | 0.0792* | |
H33b | 0.0684 | 0.5645 | 0.6017 | 0.0792* | |
H33c | 0.1044 | 0.4723 | 0.6562 | 0.0792* | |
H34a | 0.1912 | 0.6114 | 0.5210 | 0.0833* | |
H34b | 0.0911 | 0.6039 | 0.4873 | 0.0833* | |
H34c | 0.1455 | 0.5431 | 0.4508 | 0.0833* | |
H1O | 0.1191 | 0.2751 | 0.7480 | 0.0576* | 0.65 |
H1O' | 0.2708 | 0.1285 | 0.6220 | 0.0532* | 0.35 |
H4O | 0.0629 | 0.0857 | 0.3508 | 0.0798* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Zn1 | 0.064 (1) | 0.060 (1) | 0.0580 (10) | 0.002 (1) | 0.0290 (8) | −0.000 (1) |
S1 | 0.070 (2) | 0.072 (2) | 0.072 (2) | −0.003 (2) | 0.035 (2) | 0.003 (2) |
S2 | 0.058 (2) | 0.064 (2) | 0.071 (2) | 0.001 (2) | 0.029 (2) | 0.000 (2) |
O2 | 0.067 (6) | 0.056 (6) | 0.079 (6) | 0.029 (5) | 0.025 (5) | 0.008 (5) |
O3 | 0.083 (6) | 0.084 (6) | 0.062 (6) | −0.031 (5) | 0.038 (5) | −0.020 (5) |
O4 | 0.064 (6) | 0.063 (6) | 0.074 (6) | −0.006 (5) | 0.026 (5) | 0.001 (5) |
O5 | 0.049 (5) | 0.093 (7) | 0.066 (6) | −0.028 (5) | 0.027 (5) | −0.025 (5) |
O6 | 0.064 (6) | 0.062 (5) | 0.061 (5) | −0.001 (5) | 0.035 (5) | 0.009 (4) |
O7 | 0.071 (6) | 0.045 (5) | 0.068 (5) | 0.025 (5) | 0.030 (5) | 0.007 (5) |
O8 | 0.080 (6) | 0.053 (5) | 0.075 (5) | −0.007 (4) | 0.048 (5) | 0.013 (4) |
C1 | 0.035 (8) | 0.059 (9) | 0.045 (8) | −0.014 (7) | 0.001 (7) | −0.008 (7) |
C2 | 0.063 (10) | 0.041 (7) | 0.058 (9) | −0.008 (7) | 0.016 (8) | −0.013 (7) |
C3 | 0.048 (8) | 0.043 (8) | 0.048 (8) | 0.001 (7) | 0.011 (7) | 0.009 (7) |
C4 | 0.07 (1) | 0.070 (10) | 0.053 (9) | −0.018 (8) | 0.038 (9) | 0.011 (8) |
C5 | 0.043 (8) | 0.055 (9) | 0.074 (10) | 0.014 (7) | −0.002 (7) | 0.031 (8) |
C6 | 0.052 (9) | 0.043 (8) | 0.061 (9) | −0.007 (7) | 0.001 (8) | 0.020 (7) |
C7 | 0.052 (9) | 0.046 (8) | 0.075 (9) | 0.001 (7) | 0.027 (8) | 0.014 (7) |
C8 | 0.055 (9) | 0.13 (1) | 0.08 (1) | 0.056 (10) | 0.024 (9) | 0.020 (10) |
C12 | 0.11 (1) | 0.12 (1) | 0.026 (7) | 0.02 (1) | 0.033 (8) | 0.010 (8) |
C16 | 0.060 (9) | 0.066 (9) | 0.044 (8) | −0.017 (8) | 0.017 (7) | −0.007 (8) |
C17 | 0.052 (9) | 0.059 (10) | 0.076 (10) | −0.011 (7) | 0.033 (8) | −0.007 (7) |
C18 | 0.051 (8) | 0.073 (10) | 0.030 (6) | 0.029 (7) | 0.017 (6) | 0.019 (6) |
C19 | 0.054 (8) | 0.057 (8) | 0.060 (8) | 0.017 (8) | 0.025 (7) | 0.020 (8) |
C20 | 0.06 (1) | 0.065 (10) | 0.069 (10) | 0.021 (8) | 0.033 (8) | 0.008 (8) |
C21 | 0.08 (1) | 0.054 (9) | 0.048 (9) | 0.023 (8) | 0.016 (8) | 0.004 (7) |
C22 | 0.046 (9) | 0.050 (9) | 0.068 (10) | −0.004 (7) | 0.022 (8) | 0.013 (7) |
C23 | 0.063 (10) | 0.053 (9) | 0.067 (9) | 0.022 (8) | 0.023 (8) | 0.002 (8) |
C24 | 0.10 (1) | 0.074 (10) | 0.084 (10) | −0.005 (9) | 0.067 (9) | 0.002 (8) |
C25 | 0.072 (8) | 0.068 (8) | 0.068 (8) | 0.008 (8) | 0.034 (7) | 0.001 (8) |
C26 | 0.068 (9) | 0.070 (10) | 0.11 (1) | −0.004 (8) | 0.043 (9) | 0.012 (9) |
C27 | 0.08 (1) | 0.08 (1) | 0.067 (10) | 0.008 (9) | 0.042 (9) | −0.018 (9) |
C28 | 0.09 (1) | 0.11 (1) | 0.08 (1) | −0.002 (10) | 0.024 (9) | −0.027 (9) |
C29 | 0.16 (1) | 0.08 (1) | 0.07 (1) | −0.00 (1) | 0.07 (1) | −0.010 (9) |
C30 | 0.10 (1) | 0.10 (1) | 0.08 (1) | −0.039 (9) | 0.046 (9) | −0.039 (9) |
C31 | 0.105 (10) | 0.090 (10) | 0.051 (8) | −0.002 (8) | 0.050 (8) | −0.009 (7) |
C32 | 0.079 (10) | 0.048 (8) | 0.084 (10) | 0.005 (7) | 0.034 (8) | 0.018 (7) |
C33 | 0.082 (9) | 0.067 (9) | 0.061 (8) | −0.005 (7) | 0.040 (7) | −0.013 (7) |
C34 | 0.069 (9) | 0.072 (9) | 0.064 (9) | 0.002 (7) | 0.021 (8) | 0.013 (7) |
Geometric parameters (Å, º) top
Zn1—O3 | 1.962 (8) | C13—H13c | 0.950 |
Zn1—O6 | 1.984 (7) | C13A—H13Aa | 0.950 |
Zn1—O7 | 1.981 (6) | C13A—H13Ab | 0.950 |
Zn1—O8 | 1.997 (6) | C13A—H13Ac | 0.950 |
S1—O8 | 1.533 (6) | C14—H14a | 0.950 |
S1—C31 | 1.79 (1) | C14—H14b | 0.950 |
S1—C32 | 1.77 (1) | C14—H14c | 0.950 |
S2—O7 | 1.535 (7) | C14A—H14Aa | 0.950 |
S2—C33 | 1.79 (1) | C14A—H14Ab | 0.950 |
S2—C34 | 1.79 (1) | C14A—H14Ac | 0.950 |
O1—C7 | 1.32 (1) | C15—H15a | 0.950 |
O1—H1O | 0.950 | C15—H15b | 0.950 |
O1A—C3 | 1.24 (2) | C15—H15c | 0.950 |
O1A—H1O' | 0.950 | C15A—H15Aa | 0.950 |
O2—C1 | 1.26 (1) | C15A—H15Ab | 0.950 |
O3—C1 | 1.29 (1) | C15A—H15Ac | 0.950 |
O4—C22 | 1.37 (1) | C16—C17 | 1.50 (1) |
O4—H4O | 0.950 | C17—C18 | 1.38 (1) |
O5—C16 | 1.22 (1) | C17—C22 | 1.40 (1) |
O6—C16 | 1.31 (1) | C18—C19 | 1.39 (1) |
C1—C2 | 1.51 (1) | C18—H18 | 0.950 |
C2—C3 | 1.41 (1) | C19—C20 | 1.42 (1) |
C2—C7 | 1.44 (1) | C19—C23 | 1.53 (1) |
C3—C4 | 1.38 (1) | C20—C21 | 1.38 (1) |
C3—H3 | 0.950 | C20—H20 | 0.950 |
C4—C5 | 1.43 (1) | C21—C22 | 1.46 (1) |
C4—C8 | 1.53 (2) | C21—C27 | 1.54 (2) |
C5—C6 | 1.42 (1) | C23—C24 | 1.53 (1) |
C5—H5 | 0.950 | C23—C25 | 1.49 (1) |
C6—C7 | 1.41 (1) | C23—C26 | 1.52 (1) |
C6—C12 | 1.59 (1) | C24—H24a | 0.950 |
C7—H7 | 0.950 | C24—H24b | 0.950 |
C8—C9 | 1.62 (2) | C24—H24c | 0.950 |
C8—C9A | 1.47 (5) | C25—H25a | 0.950 |
C8—C10 | 1.47 (2) | C25—H25b | 0.950 |
C8—C10A | 1.63 (4) | C25—H25c | 0.950 |
C8—C11 | 1.63 (2) | C26—H26a | 0.950 |
C8—C11A | 1.66 (4) | C26—H26b | 0.950 |
C9—H9a | 0.950 | C26—H26c | 0.950 |
C9—H9b | 0.950 | C27—C28 | 1.51 (1) |
C9—H9c | 0.950 | C27—C29 | 1.53 (2) |
C9A—H9Aa | 0.950 | C27—C30 | 1.56 (1) |
C9A—H9Ab | 0.950 | C28—H28a | 0.950 |
C9A—H9Ac | 0.950 | C28—H28b | 0.950 |
C10—H10a | 0.950 | C28—H28c | 0.950 |
C10—H10b | 0.950 | C29—H29a | 0.950 |
C10—H10c | 0.950 | C29—H29b | 0.950 |
C10A—H10Aa | 0.950 | C29—H29c | 0.950 |
C10A—H10Ab | 0.950 | C30—H30a | 0.950 |
C10A—H10Ac | 0.950 | C30—H30b | 0.950 |
C11—H11a | 0.950 | C30—H30c | 0.950 |
C11—H11b | 0.950 | C31—H31a | 0.950 |
C11—H11c | 0.950 | C31—H31b | 0.950 |
C11A—H11Aa | 0.950 | C31—H31c | 0.950 |
C11A—H11Ab | 0.950 | C32—H32a | 0.950 |
C11A—H11Ac | 0.950 | C32—H32b | 0.950 |
C12—C13 | 1.55 (2) | C32—H32c | 0.950 |
C12—C13A | 1.53 (3) | C33—H33a | 0.950 |
C12—C14 | 1.58 (2) | C33—H33b | 0.950 |
C12—C14A | 1.54 (3) | C33—H33c | 0.950 |
C12—C15 | 1.54 (2) | C34—H34a | 0.950 |
C12—C15A | 1.61 (3) | C34—H34b | 0.950 |
C13—H13a | 0.950 | C34—H34c | 0.950 |
C13—H13b | 0.950 | | |
| | | |
O1···C11Ai | 3.06 (4) | O6···C32iv | 3.35 (1) |
O1···C10i | 3.31 (2) | O7···C33v | 3.39 (1) |
O1A···C31ii | 3.44 (2) | O7···O7v | 3.44 (1) |
O1A···C34iii | 3.49 (2) | O7···C34v | 3.50 (1) |
O2···C11Ai | 3.49 (4) | C9A···C18iii | 3.44 (5) |
O3···C32iv | 3.37 (1) | C9A···C17iii | 3.54 (5) |
O4···C24i | 3.44 (1) | C10···C15Aii | 3.42 (4) |
O5···C32ii | 3.29 (1) | C10A···C13vi | 3.18 (4) |
O5···C31ii | 3.52 (1) | | |
| | | |
O3—Zn1—O6 | 109.4 (3) | C19—C20—H20 | 117.6 |
O3—Zn1—O7 | 116.5 (3) | C21—C20—H20 | 117.6 |
O3—Zn1—O8 | 113.7 (3) | C20—C21—C22 | 115 (1) |
O6—Zn1—O7 | 113.7 (3) | C20—C21—C27 | 124 (1) |
O6—Zn1—O8 | 100.8 (3) | C22—C21—C27 | 119 (1) |
O7—Zn1—O8 | 101.6 (3) | O4—C22—C17 | 119 (1) |
O8—S1—C31 | 106.2 (5) | O4—C22—C21 | 119 (1) |
O8—S1—C32 | 103.6 (5) | C17—C22—C21 | 120 (1) |
C31—S1—C32 | 97.8 (5) | C19—C23—C24 | 110 (1) |
O7—S2—C33 | 103.8 (4) | C19—C23—C25 | 111 (1) |
O7—S2—C34 | 103.3 (5) | C19—C23—C26 | 110.2 (10) |
C33—S2—C34 | 99.2 (5) | C24—C23—C25 | 107.2 (10) |
C7—O1—H1O | 120.0 | C24—C23—C26 | 105 (1) |
C3—O1A—H1O' | 120.0 | C25—C23—C26 | 111 (1) |
Zn1—O3—C1 | 108.6 (7) | C23—C24—H24a | 109.5 |
C22—O4—H4O | 120.0 | C23—C24—H24b | 109.5 |
Zn1—O6—C16 | 106.2 (7) | C23—C24—H24c | 109.5 |
Zn1—O7—S2 | 116.2 (4) | H24a—C24—H24b | 109.5 |
Zn1—O8—S1 | 120.7 (4) | H24a—C24—H24c | 109.5 |
O2—C1—O3 | 123 (1) | H24b—C24—H24c | 109.5 |
O2—C1—C2 | 120 (1) | C23—C25—H25a | 109.5 |
O3—C1—C2 | 115 (1) | C23—C25—H25b | 109.5 |
C1—C2—C3 | 121 (1) | C23—C25—H25c | 109.5 |
C1—C2—C7 | 118 (1) | H25a—C25—H25b | 109.5 |
C3—C2—C7 | 119 (1) | H25a—C25—H25c | 109.5 |
O1A—C3—C2 | 116 (1) | H25b—C25—H25c | 109.5 |
O1A—C3—C4 | 120 (1) | C23—C26—H26a | 109.5 |
C2—C3—C4 | 122 (1) | C23—C26—H26b | 109.5 |
C2—C3—H3 | 118.6 | C23—C26—H26c | 109.5 |
C4—C3—H3 | 118.6 | H26a—C26—H26b | 109.5 |
C3—C4—C5 | 115 (1) | H26a—C26—H26c | 109.5 |
C3—C4—C8 | 126 (1) | H26b—C26—H26c | 109.5 |
C5—C4—C8 | 117 (1) | C21—C27—C28 | 111 (1) |
C4—C5—C6 | 124 (1) | C21—C27—C29 | 111 (1) |
C4—C5—H5 | 117.6 | C21—C27—C30 | 108 (1) |
C6—C5—H5 | 117.6 | C28—C27—C29 | 112 (1) |
C5—C6—C7 | 116 (1) | C28—C27—C30 | 105 (1) |
C5—C6—C12 | 123 (1) | C29—C27—C30 | 107.1 (10) |
C7—C6—C12 | 119 (1) | C27—C28—H28a | 109.5 |
O1—C7—C2 | 116 (1) | C27—C28—H28b | 109.5 |
O1—C7—C6 | 122 (1) | C27—C28—H28c | 109.5 |
C2—C7—C6 | 120 (1) | H28a—C28—H28b | 109.5 |
C2—C7—H7 | 119.9 | H28a—C28—H28c | 109.5 |
C6—C7—H7 | 119.9 | H28b—C28—H28c | 109.5 |
C4—C8—C9 | 109 (1) | C27—C29—H29a | 109.5 |
C4—C8—C9A | 109 (2) | C27—C29—H29b | 109.5 |
C4—C8—C10 | 114 (1) | C27—C29—H29c | 109.5 |
C4—C8—C10A | 108 (1) | H29a—C29—H29b | 109.5 |
C4—C8—C11 | 109 (1) | H29a—C29—H29c | 109.5 |
C4—C8—C11A | 101 (1) | H29b—C29—H29c | 109.5 |
C9—C8—C10 | 114 (1) | C27—C30—H30a | 109.5 |
C9—C8—C11 | 101 (1) | C27—C30—H30b | 109.5 |
C9A—C8—C10A | 137 (2) | C27—C30—H30c | 109.5 |
C9A—C8—C11A | 98 (2) | H30a—C30—H30b | 109.5 |
C10—C8—C11 | 105 (1) | H30a—C30—H30c | 109.5 |
C10A—C8—C11A | 93 (1) | H30b—C30—H30c | 109.5 |
C6—C12—C13 | 106 (1) | S1—C31—H31a | 109.5 |
C6—C12—C13A | 111 (1) | S1—C31—H31b | 109.5 |
C6—C12—C14 | 105 (1) | S1—C31—H31c | 109.5 |
C6—C12—C14A | 110 (1) | H31a—C31—H31b | 109.5 |
C6—C12—C15 | 109 (1) | H31a—C31—H31c | 109.5 |
C6—C12—C15A | 114 (1) | H31b—C31—H31c | 109.5 |
C13—C12—C14 | 108 (1) | S1—C32—H32a | 109.5 |
C13—C12—C15 | 112 (1) | S1—C32—H32b | 109.5 |
C13A—C12—C14A | 99 (2) | S1—C32—H32c | 109.5 |
C13A—C12—C15A | 109 (2) | H32a—C32—H32b | 109.5 |
C14—C12—C15 | 113 (1) | H32a—C32—H32c | 109.5 |
C14A—C12—C15A | 110 (2) | H32b—C32—H32c | 109.5 |
O5—C16—O6 | 122 (1) | S2—C33—H33a | 109.5 |
O5—C16—C17 | 121 (1) | S2—C33—H33b | 109.5 |
O6—C16—C17 | 115 (1) | S2—C33—H33c | 109.5 |
C16—C17—C18 | 116 (1) | H33a—C33—H33b | 109.5 |
C16—C17—C22 | 122 (1) | H33a—C33—H33c | 109.5 |
C18—C17—C22 | 120 (1) | H33b—C33—H33c | 109.5 |
C17—C18—C19 | 121 (1) | S2—C34—H34a | 109.5 |
C17—C18—H18 | 119.2 | S2—C34—H34b | 109.5 |
C19—C18—H18 | 119.2 | S2—C34—H34c | 109.5 |
C18—C19—C20 | 116 (1) | H34a—C34—H34b | 109.5 |
C18—C19—C23 | 126 (1) | H34a—C34—H34c | 109.5 |
C20—C19—C23 | 116 (1) | H34b—C34—H34c | 109.5 |
C19—C20—C21 | 124 (1) | | |
Symmetry codes: (i) x−1/2, −y+1/2, z; (ii) x+1/2, −y+1/2, z; (iii) −x+1/2, y−1/2, −z+1; (iv) −x, −y, −z+1; (v) −x, −y+1, −z+1; (vi) −x+1, −y, −z+2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O···O2 | 0.95 | 1.66 | 2.45 (1) | 138 |
O1A—H1O′···O3 | 0.95 | 1.62 | 2.41 (1) | 140 |
O4—H4O···O6 | 0.95 | 1.79 | 2.52 (1) | 131 |