Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053681401736X/wm5037sup1.cif | |
Microsoft Word (DOCX) file https://doi.org/10.1107/S160053681401736X/wm5037Isup2.docx | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053681401736X/wm5037Isup3.hkl | |
Chemdraw file https://doi.org/10.1107/S160053681401736X/wm5037Isup5.cdx |
CCDC reference: 1013307
Key indicators
Structure: I- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.003 Å
- R factor = 0.029
- wR factor = 0.079
- Data-to-parameter ratio = 16.2
checkCIF/PLATON results
No syntax errors found
Alert level B Crystal system given = monoclinic PLAT094_ALERT_2_B Ratio of Maximum / Minimum Residual Density .... 4.29 Report PLAT420_ALERT_2_B D-H Without Acceptor O1 - H1 ... Please Check
0 ALERT level A = Most likely a serious problem - resolve or explain 2 ALERT level B = A potentially serious problem, consider carefully 0 ALERT level C = Check. Ensure it is not caused by an omission or oversight 0 ALERT level G = General information/check it is not something unexpected 0 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 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
The complex was synthesized from the reaction of water with the [Zn(Et)(N,N'-bis(2,6-dimethylphenyl)pentane-2,4-diiminato)] complex in Et2O. The solvent was removed under vacuum after the reaction, and a white powder was collected. Recrystallization of the white powder in saturated Et2O at 253 K led to the formation of colorless crystals.
The positions of hydrogen atoms bonded to carbon atoms were initially determined by geometrical considerations and refined by using a riding model. The hydrogen atom bonded to the oxygen atom was located in a difference map, and its position was refined independently. Hydrogen atom displacement parameters were set to 1.2Ueq (1.5 for methyl) of the respective parent atom.
Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL2012 (Sheldrick, 2008).
[Zn2(C21H25N2)2(OH)2] | F(000) = 816 |
Mr = 775.61 | Dx = 1.355 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 12.8736 (4) Å | Cell parameters from 7335 reflections |
b = 8.7682 (3) Å | θ = 2.3–28.3° |
c = 17.4530 (5) Å | µ = 1.30 mm−1 |
β = 105.222 (2)° | T = 100 K |
V = 1900.95 (10) Å3 | Block, colorless |
Z = 2 | 0.46 × 0.23 × 0.23 mm |
Bruker APEX CCD diffractometer | 3576 reflections with I > 2σ(I) |
ϕ and ω scans | Rint = 0.016 |
Absorption correction: multi-scan (SADABS; Bruker, 2007) | θmax = 26.0°, θmin = 1.8° |
Tmin = 0.586, Tmax = 0.754 | h = −15→15 |
22627 measured reflections | k = −10→10 |
3730 independent reflections | l = −21→21 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.029 | Hydrogen site location: mixed |
wR(F2) = 0.079 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.99 | w = 1/[σ2(Fo2) + (0.050P)2 + 1.390P]
where P = (Fo2 + 2Fc2)/3 |
3730 reflections | (Δ/σ)max = 0.002 |
230 parameters | Δρmax = 1.06 e Å−3 |
0 restraints | Δρmin = −0.25 e Å−3 |
[Zn2(C21H25N2)2(OH)2] | V = 1900.95 (10) Å3 |
Mr = 775.61 | Z = 2 |
Monoclinic, P21/n | Mo Kα radiation |
a = 12.8736 (4) Å | µ = 1.30 mm−1 |
b = 8.7682 (3) Å | T = 100 K |
c = 17.4530 (5) Å | 0.46 × 0.23 × 0.23 mm |
β = 105.222 (2)° |
Bruker APEX CCD diffractometer | 3730 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2007) | 3576 reflections with I > 2σ(I) |
Tmin = 0.586, Tmax = 0.754 | Rint = 0.016 |
22627 measured reflections |
R[F2 > 2σ(F2)] = 0.029 | 0 restraints |
wR(F2) = 0.079 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.99 | Δρmax = 1.06 e Å−3 |
3730 reflections | Δρmin = −0.25 e Å−3 |
230 parameters |
x | y | z | Uiso*/Ueq | ||
Zn1 | 0.95859 (2) | 0.92266 (2) | 0.92324 (2) | 0.02197 (9) | |
N1 | 1.01789 (11) | 0.88907 (16) | 0.83143 (8) | 0.0201 (3) | |
N2 | 0.81321 (11) | 0.83790 (17) | 0.87559 (8) | 0.0228 (3) | |
O1 | 0.96361 (10) | 1.13369 (16) | 0.96789 (7) | 0.0259 (3) | |
H1 | 0.9667 (18) | 1.209 (3) | 0.9400 (15) | 0.038 (7)* | |
C3 | 0.95099 (13) | 0.87215 (19) | 0.75919 (10) | 0.0210 (3) | |
C4 | 0.83960 (13) | 0.8525 (2) | 0.74383 (10) | 0.0223 (3) | |
H4 | 0.8007 | 0.8593 | 0.6896 | 0.027* | |
C5 | 0.77700 (13) | 0.8241 (2) | 0.79754 (10) | 0.0225 (3) | |
C6 | 0.99662 (14) | 0.8736 (2) | 0.68752 (10) | 0.0262 (4) | |
H6A | 1.0405 | 0.9654 | 0.6889 | 0.039* | |
H6B | 0.9375 | 0.8735 | 0.6389 | 0.039* | |
H6C | 1.0414 | 0.7829 | 0.6884 | 0.039* | |
C7 | 0.66271 (13) | 0.7706 (2) | 0.76132 (10) | 0.0267 (4) | |
H7A | 0.6537 | 0.6674 | 0.7802 | 0.040* | |
H7B | 0.6483 | 0.7698 | 0.7033 | 0.040* | |
H7C | 0.6123 | 0.8399 | 0.7770 | 0.040* | |
C8 | 0.74730 (13) | 0.7795 (2) | 0.92370 (10) | 0.0241 (4) | |
C9 | 0.76109 (14) | 0.6264 (2) | 0.94808 (10) | 0.0259 (4) | |
C10 | 0.69362 (16) | 0.5658 (2) | 0.99114 (11) | 0.0305 (4) | |
H10 | 0.7011 | 0.4621 | 1.0074 | 0.037* | |
C11 | 0.61560 (15) | 0.6562 (3) | 1.01037 (11) | 0.0335 (4) | |
H11 | 0.5684 | 0.6135 | 1.0383 | 0.040* | |
C12 | 0.60651 (14) | 0.8085 (3) | 0.98893 (11) | 0.0333 (4) | |
H12 | 0.5541 | 0.8698 | 1.0037 | 0.040* | |
C13 | 0.67270 (14) | 0.8742 (2) | 0.94604 (11) | 0.0294 (4) | |
C14 | 0.84837 (15) | 0.5304 (2) | 0.92859 (12) | 0.0309 (4) | |
H14A | 0.8418 | 0.4248 | 0.9451 | 0.046* | |
H14B | 0.9191 | 0.5707 | 0.9568 | 0.046* | |
H14C | 0.8408 | 0.5334 | 0.8712 | 0.046* | |
C15 | 0.66482 (18) | 1.0416 (3) | 0.92477 (14) | 0.0394 (5) | |
H15A | 0.7365 | 1.0880 | 0.9413 | 0.059* | |
H15B | 0.6168 | 1.0925 | 0.9520 | 0.059* | |
H15C | 0.6360 | 1.0530 | 0.8672 | 0.059* | |
C16 | 1.13079 (13) | 0.8705 (2) | 0.83836 (9) | 0.0205 (3) | |
C17 | 1.17176 (14) | 0.7214 (2) | 0.84038 (10) | 0.0238 (3) | |
C18 | 1.28096 (14) | 0.7028 (2) | 0.84487 (11) | 0.0281 (4) | |
H18 | 1.3101 | 0.6030 | 0.8463 | 0.034* | |
C19 | 1.34732 (14) | 0.8281 (2) | 0.84731 (11) | 0.0290 (4) | |
H19 | 1.4212 | 0.8140 | 0.8494 | 0.035* | |
C20 | 1.30597 (14) | 0.9738 (2) | 0.84663 (10) | 0.0277 (4) | |
H20 | 1.3522 | 1.0591 | 0.8488 | 0.033* | |
C21 | 1.19747 (14) | 0.9978 (2) | 0.84288 (10) | 0.0228 (3) | |
C22 | 1.09984 (17) | 0.5850 (2) | 0.83697 (13) | 0.0314 (4) | |
H22A | 1.0652 | 0.5902 | 0.8806 | 0.047* | |
H22B | 1.1429 | 0.4916 | 0.8419 | 0.047* | |
H22C | 1.0446 | 0.5843 | 0.7862 | 0.047* | |
C23 | 1.15467 (15) | 1.1575 (2) | 0.84357 (11) | 0.0285 (4) | |
H23A | 1.0852 | 1.1661 | 0.8038 | 0.043* | |
H23B | 1.2058 | 1.2301 | 0.8311 | 0.043* | |
H23C | 1.1452 | 1.1803 | 0.8963 | 0.043* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Zn1 | 0.01621 (12) | 0.03297 (14) | 0.01712 (12) | 0.00048 (7) | 0.00511 (8) | −0.00413 (7) |
N1 | 0.0170 (7) | 0.0258 (7) | 0.0179 (7) | 0.0004 (5) | 0.0054 (5) | −0.0020 (5) |
N2 | 0.0172 (6) | 0.0314 (8) | 0.0201 (7) | 0.0002 (6) | 0.0056 (5) | 0.0005 (6) |
O1 | 0.0264 (6) | 0.0323 (7) | 0.0186 (6) | 0.0012 (5) | 0.0052 (5) | −0.0017 (5) |
C3 | 0.0231 (8) | 0.0214 (8) | 0.0196 (8) | 0.0010 (6) | 0.0074 (6) | −0.0003 (6) |
C4 | 0.0212 (8) | 0.0272 (9) | 0.0179 (8) | 0.0000 (6) | 0.0039 (6) | 0.0015 (6) |
C5 | 0.0190 (8) | 0.0248 (8) | 0.0226 (8) | 0.0014 (6) | 0.0037 (6) | 0.0023 (7) |
C6 | 0.0239 (8) | 0.0366 (10) | 0.0191 (8) | −0.0015 (7) | 0.0073 (7) | −0.0002 (7) |
C7 | 0.0204 (8) | 0.0353 (10) | 0.0227 (8) | −0.0037 (7) | 0.0028 (7) | 0.0038 (7) |
C8 | 0.0164 (7) | 0.0375 (10) | 0.0177 (8) | −0.0011 (7) | 0.0033 (6) | 0.0005 (7) |
C9 | 0.0215 (8) | 0.0347 (9) | 0.0201 (8) | −0.0020 (7) | 0.0029 (7) | −0.0022 (7) |
C10 | 0.0296 (10) | 0.0388 (11) | 0.0216 (9) | −0.0083 (8) | 0.0040 (7) | 0.0017 (7) |
C11 | 0.0255 (9) | 0.0542 (13) | 0.0217 (9) | −0.0101 (9) | 0.0081 (7) | −0.0004 (8) |
C12 | 0.0205 (8) | 0.0561 (13) | 0.0243 (9) | 0.0028 (8) | 0.0078 (7) | −0.0023 (8) |
C13 | 0.0208 (8) | 0.0431 (11) | 0.0242 (9) | 0.0042 (8) | 0.0057 (7) | 0.0024 (8) |
C14 | 0.0295 (9) | 0.0311 (10) | 0.0318 (10) | 0.0015 (8) | 0.0077 (8) | −0.0006 (8) |
C15 | 0.0364 (11) | 0.0441 (12) | 0.0418 (12) | 0.0127 (9) | 0.0177 (9) | 0.0040 (10) |
C16 | 0.0187 (8) | 0.0280 (9) | 0.0157 (7) | 0.0011 (6) | 0.0062 (6) | −0.0011 (6) |
C17 | 0.0251 (8) | 0.0276 (9) | 0.0204 (8) | 0.0023 (7) | 0.0087 (6) | −0.0009 (7) |
C18 | 0.0274 (9) | 0.0340 (10) | 0.0248 (9) | 0.0089 (7) | 0.0102 (7) | 0.0017 (7) |
C19 | 0.0185 (8) | 0.0461 (11) | 0.0235 (9) | 0.0032 (7) | 0.0071 (7) | −0.0007 (8) |
C20 | 0.0220 (8) | 0.0392 (10) | 0.0226 (9) | −0.0064 (7) | 0.0072 (7) | −0.0025 (8) |
C21 | 0.0243 (8) | 0.0281 (9) | 0.0167 (8) | −0.0002 (7) | 0.0066 (6) | −0.0006 (6) |
C22 | 0.0341 (10) | 0.0249 (9) | 0.0386 (11) | 0.0014 (7) | 0.0154 (9) | −0.0015 (7) |
C23 | 0.0315 (9) | 0.0258 (9) | 0.0296 (9) | −0.0016 (7) | 0.0104 (7) | −0.0007 (7) |
Zn1—O1i | 1.9643 (13) | C11—H11 | 0.9500 |
Zn1—N1 | 1.9696 (14) | C12—C13 | 1.397 (3) |
Zn1—N2 | 1.9823 (14) | C12—H12 | 0.9500 |
Zn1—O1 | 2.0022 (14) | C13—C15 | 1.511 (3) |
N1—C3 | 1.335 (2) | C14—H14A | 0.9800 |
N1—C16 | 1.436 (2) | C14—H14B | 0.9800 |
N2—C5 | 1.324 (2) | C14—H14C | 0.9800 |
N2—C8 | 1.436 (2) | C15—H15A | 0.9800 |
O1—H1 | 0.83 (3) | C15—H15B | 0.9800 |
C3—C4 | 1.398 (2) | C15—H15C | 0.9800 |
C3—C6 | 1.515 (2) | C16—C21 | 1.398 (2) |
C4—C5 | 1.410 (2) | C16—C17 | 1.407 (2) |
C4—H4 | 0.9500 | C17—C18 | 1.397 (2) |
C5—C7 | 1.515 (2) | C17—C22 | 1.504 (3) |
C6—H6A | 0.9800 | C18—C19 | 1.386 (3) |
C6—H6B | 0.9800 | C18—H18 | 0.9500 |
C6—H6C | 0.9800 | C19—C20 | 1.383 (3) |
C7—H7A | 0.9800 | C19—H19 | 0.9500 |
C7—H7B | 0.9800 | C20—C21 | 1.397 (2) |
C7—H7C | 0.9800 | C20—H20 | 0.9500 |
C8—C13 | 1.400 (3) | C21—C23 | 1.506 (3) |
C8—C9 | 1.406 (3) | C22—H22A | 0.9800 |
C9—C10 | 1.394 (3) | C22—H22B | 0.9800 |
C9—C14 | 1.512 (3) | C22—H22C | 0.9800 |
C10—C11 | 1.388 (3) | C23—H23A | 0.9800 |
C10—H10 | 0.9500 | C23—H23B | 0.9800 |
C11—C12 | 1.383 (3) | C23—H23C | 0.9800 |
O1i—Zn1—N1 | 122.77 (6) | C11—C12—C13 | 121.50 (18) |
O1i—Zn1—N2 | 119.80 (6) | C11—C12—H12 | 119.2 |
N1—Zn1—N2 | 97.33 (6) | C13—C12—H12 | 119.2 |
O1i—Zn1—O1 | 84.25 (6) | C12—C13—C8 | 117.67 (19) |
N1—Zn1—O1 | 118.36 (6) | C12—C13—C15 | 121.39 (18) |
N2—Zn1—O1 | 116.11 (6) | C8—C13—C15 | 120.94 (17) |
C3—N1—C16 | 117.04 (14) | C9—C14—H14A | 109.5 |
C3—N1—Zn1 | 119.54 (11) | C9—C14—H14B | 109.5 |
C16—N1—Zn1 | 123.26 (11) | H14A—C14—H14B | 109.5 |
C5—N2—C8 | 117.81 (14) | C9—C14—H14C | 109.5 |
C5—N2—Zn1 | 120.29 (11) | H14A—C14—H14C | 109.5 |
C8—N2—Zn1 | 121.74 (11) | H14B—C14—H14C | 109.5 |
Zn1i—O1—Zn1 | 95.75 (6) | C13—C15—H15A | 109.5 |
Zn1i—O1—H1 | 132.7 (17) | C13—C15—H15B | 109.5 |
Zn1—O1—H1 | 120.8 (17) | H15A—C15—H15B | 109.5 |
N1—C3—C4 | 124.70 (15) | C13—C15—H15C | 109.5 |
N1—C3—C6 | 118.99 (15) | H15A—C15—H15C | 109.5 |
C4—C3—C6 | 116.30 (15) | H15B—C15—H15C | 109.5 |
C3—C4—C5 | 129.11 (15) | C21—C16—C17 | 121.33 (15) |
C3—C4—H4 | 115.4 | C21—C16—N1 | 120.49 (15) |
C5—C4—H4 | 115.4 | C17—C16—N1 | 118.17 (15) |
N2—C5—C4 | 124.02 (15) | C18—C17—C16 | 118.38 (16) |
N2—C5—C7 | 119.89 (15) | C18—C17—C22 | 120.61 (17) |
C4—C5—C7 | 116.07 (15) | C16—C17—C22 | 121.01 (15) |
C3—C6—H6A | 109.5 | C19—C18—C17 | 120.81 (17) |
C3—C6—H6B | 109.5 | C19—C18—H18 | 119.6 |
H6A—C6—H6B | 109.5 | C17—C18—H18 | 119.6 |
C3—C6—H6C | 109.5 | C20—C19—C18 | 119.98 (16) |
H6A—C6—H6C | 109.5 | C20—C19—H19 | 120.0 |
H6B—C6—H6C | 109.5 | C18—C19—H19 | 120.0 |
C5—C7—H7A | 109.5 | C19—C20—C21 | 121.15 (18) |
C5—C7—H7B | 109.5 | C19—C20—H20 | 119.4 |
H7A—C7—H7B | 109.5 | C21—C20—H20 | 119.4 |
C5—C7—H7C | 109.5 | C20—C21—C16 | 118.32 (17) |
H7A—C7—H7C | 109.5 | C20—C21—C23 | 120.18 (17) |
H7B—C7—H7C | 109.5 | C16—C21—C23 | 121.50 (16) |
C13—C8—C9 | 121.56 (16) | C17—C22—H22A | 109.5 |
C13—C8—N2 | 120.37 (17) | C17—C22—H22B | 109.5 |
C9—C8—N2 | 118.06 (15) | H22A—C22—H22B | 109.5 |
C10—C9—C8 | 118.67 (17) | C17—C22—H22C | 109.5 |
C10—C9—C14 | 120.93 (18) | H22A—C22—H22C | 109.5 |
C8—C9—C14 | 120.39 (16) | H22B—C22—H22C | 109.5 |
C11—C10—C9 | 120.38 (19) | C21—C23—H23A | 109.5 |
C11—C10—H10 | 119.8 | C21—C23—H23B | 109.5 |
C9—C10—H10 | 119.8 | H23A—C23—H23B | 109.5 |
C12—C11—C10 | 120.06 (17) | C21—C23—H23C | 109.5 |
C12—C11—H11 | 120.0 | H23A—C23—H23C | 109.5 |
C10—C11—H11 | 120.0 | H23B—C23—H23C | 109.5 |
C16—N1—C3—C4 | 165.14 (16) | C11—C12—C13—C8 | 1.5 (3) |
Zn1—N1—C3—C4 | −10.5 (2) | C11—C12—C13—C15 | −178.18 (19) |
C16—N1—C3—C6 | −14.8 (2) | C9—C8—C13—C12 | −4.5 (3) |
Zn1—N1—C3—C6 | 169.60 (12) | N2—C8—C13—C12 | 176.31 (16) |
N1—C3—C4—C5 | −10.3 (3) | C9—C8—C13—C15 | 175.20 (17) |
C6—C3—C4—C5 | 169.62 (18) | N2—C8—C13—C15 | −4.0 (3) |
C8—N2—C5—C4 | −169.09 (16) | C3—N1—C16—C21 | 100.95 (19) |
Zn1—N2—C5—C4 | 6.4 (2) | Zn1—N1—C16—C21 | −83.61 (18) |
C8—N2—C5—C7 | 9.1 (2) | C3—N1—C16—C17 | −79.0 (2) |
Zn1—N2—C5—C7 | −175.34 (12) | Zn1—N1—C16—C17 | 96.43 (16) |
C3—C4—C5—N2 | 12.6 (3) | C21—C16—C17—C18 | −1.7 (2) |
C3—C4—C5—C7 | −165.64 (18) | N1—C16—C17—C18 | 178.23 (15) |
C5—N2—C8—C13 | −91.7 (2) | C21—C16—C17—C22 | 178.88 (17) |
Zn1—N2—C8—C13 | 92.82 (17) | N1—C16—C17—C22 | −1.2 (2) |
C5—N2—C8—C9 | 89.03 (19) | C16—C17—C18—C19 | 0.0 (3) |
Zn1—N2—C8—C9 | −86.44 (18) | C22—C17—C18—C19 | 179.42 (17) |
C13—C8—C9—C10 | 4.2 (3) | C17—C18—C19—C20 | 1.1 (3) |
N2—C8—C9—C10 | −176.53 (15) | C18—C19—C20—C21 | −0.5 (3) |
C13—C8—C9—C14 | −175.09 (16) | C19—C20—C21—C16 | −1.1 (3) |
N2—C8—C9—C14 | 4.2 (2) | C19—C20—C21—C23 | 179.00 (16) |
C8—C9—C10—C11 | −0.9 (3) | C17—C16—C21—C20 | 2.3 (2) |
C14—C9—C10—C11 | 178.37 (17) | N1—C16—C21—C20 | −177.69 (15) |
C9—C10—C11—C12 | −2.0 (3) | C17—C16—C21—C23 | −177.87 (16) |
C10—C11—C12—C13 | 1.7 (3) | N1—C16—C21—C23 | 2.2 (2) |
Symmetry code: (i) −x+2, −y+2, −z+2. |
Experimental details
Crystal data | |
Chemical formula | [Zn2(C21H25N2)2(OH)2] |
Mr | 775.61 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 100 |
a, b, c (Å) | 12.8736 (4), 8.7682 (3), 17.4530 (5) |
β (°) | 105.222 (2) |
V (Å3) | 1900.95 (10) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.30 |
Crystal size (mm) | 0.46 × 0.23 × 0.23 |
Data collection | |
Diffractometer | Bruker APEX CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2007) |
Tmin, Tmax | 0.586, 0.754 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 22627, 3730, 3576 |
Rint | 0.016 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.029, 0.079, 0.99 |
No. of reflections | 3730 |
No. of parameters | 230 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 1.06, −0.25 |
Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008), SHELXL2012 (Sheldrick, 2008).