Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270103010205/sk1640sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270103010205/sk1640Isup2.hkl |
CCDC reference: 217141
The Schiff base was obtained by refluxing a mixture of 2-methoxysalicylaldehyde (20 mmol) and the L-(+)-tartaric acid salt of trans-(1R,2R)-1,2-diaminocyclohexane (10 mmol) in the presence of anhydrous potassium carbonate, with a methanol–water mixture as solvent. The crude product was obtained by removing the solvent at reduced pressure and was recrystallized from hexane (yield 85%; m.p. 401–403 K). Analysis found: C 69.1, H 6.4, N 7.2%; C22H26N2O4 requires: C 69.3, H 6.9, N 7.3%. IR (cm−1): 3416 (OH), 1626 (C═N); NMR (CDCl3): δ(H) 1.42–1.60 (m, 4H, CH2), 1.86–1.96 (m, 4H, CH2), 3.59 (m, 2H, CH), 3.93 (s, 6H, OCH3), 6.3–7.2 (m, 6H, aromatic), 8.24 (s, 2H, CH═N), 13.81 (s, 2H, OH); [α]23D(CH3OH), −46.9° dm−1 g−1 cm3.
Crystals of (I) are orthorhombic and the space group P212121 was uniquely assigned from the systematic absences. All H atoms were treated as riding atoms, with C—H distances of 0.95 (aromatic), 0.98 (CH3), 0.99 (CH2) or 1.00 Å (aliphatic CH), and O—H distances of 0.84 Å. In the absence of significant anomalous scattering, the Flack (1983) parameter was indeterminate (Flack & Bernardinelli, 2000); hence the Friedel equivalents were merged before the final refinements, and the absolute structure was set by reference to the known (R,R) configuration of the trans-1,2-diaminocyclohexane used in the synthesis.
Data collection: KappaCCD Server Software (Nonius, 1997); cell refinement: DENZO–SMN (Otwinowski & Minor, 1997); data reduction: DENZO–SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997) and PRPKAPPA (Ferguson, 1999).
C22H26N2O4 | F(000) = 816 |
Mr = 382.45 | Dx = 1.252 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 2642 reflections |
a = 7.5558 (2) Å | θ = 3.0–27.4° |
b = 13.4054 (1) Å | µ = 0.09 mm−1 |
c = 20.0304 (3) Å | T = 120 K |
V = 2028.85 (6) Å3 | Plate, yellow |
Z = 4 | 0.32 × 0.25 × 0.08 mm |
Nonius KappaCCD diffractometer | 2642 independent reflections |
Radiation source: rotating anode | 2484 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.071 |
ϕ scans, and ω scans with κ offsets | θmax = 27.4°, θmin = 3.0° |
Absorption correction: multi-scan DENZO–SMN (Otwinowski & Minor, 1997) | h = −9→9 |
Tmin = 0.962, Tmax = 0.994 | k = −17→17 |
27432 measured reflections | l = −25→25 |
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)] = 0.035 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.084 | H-atom parameters constrained |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0438P)2 + 0.3696P] where P = (Fo2 + 2Fc2)/3 |
2646 reflections | (Δ/σ)max < 0.001 |
257 parameters | Δρmax = 0.16 e Å−3 |
0 restraints | Δρmin = −0.22 e Å−3 |
C22H26N2O4 | V = 2028.85 (6) Å3 |
Mr = 382.45 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 7.5558 (2) Å | µ = 0.09 mm−1 |
b = 13.4054 (1) Å | T = 120 K |
c = 20.0304 (3) Å | 0.32 × 0.25 × 0.08 mm |
Nonius KappaCCD diffractometer | 2642 independent reflections |
Absorption correction: multi-scan DENZO–SMN (Otwinowski & Minor, 1997) | 2484 reflections with I > 2σ(I) |
Tmin = 0.962, Tmax = 0.994 | Rint = 0.071 |
27432 measured reflections |
R[F2 > 2σ(F2)] = 0.035 | 0 restraints |
wR(F2) = 0.084 | H-atom parameters constrained |
S = 1.08 | Δρmax = 0.16 e Å−3 |
2646 reflections | Δρmin = −0.22 e Å−3 |
257 parameters |
x | y | z | Uiso*/Ueq | ||
C1 | 1.0437 (2) | −0.11601 (12) | 0.67182 (8) | 0.0204 (3) | |
C2 | 0.9595 (2) | −0.02665 (12) | 0.70712 (8) | 0.0211 (3) | |
C3 | 1.1026 (3) | 0.04886 (13) | 0.72695 (9) | 0.0253 (4) | |
C4 | 1.2443 (3) | 0.00097 (14) | 0.77096 (9) | 0.0277 (4) | |
C5 | 1.3229 (3) | −0.09167 (14) | 0.73779 (10) | 0.0290 (4) | |
C6 | 1.1799 (3) | −0.16624 (13) | 0.71701 (9) | 0.0261 (4) | |
N11 | 0.9037 (2) | −0.18570 (10) | 0.65255 (7) | 0.0217 (3) | |
C11 | 0.7886 (2) | −0.30840 (12) | 0.57741 (8) | 0.0206 (3) | |
C12 | 0.6279 (2) | −0.31617 (12) | 0.61182 (8) | 0.0209 (3) | |
C13 | 0.5024 (2) | −0.38805 (13) | 0.59244 (8) | 0.0221 (4) | |
C14 | 0.5402 (3) | −0.45242 (13) | 0.53992 (8) | 0.0245 (4) | |
C15 | 0.7010 (3) | −0.44442 (14) | 0.50561 (8) | 0.0266 (4) | |
C16 | 0.8224 (2) | −0.37285 (14) | 0.52317 (8) | 0.0254 (4) | |
C17 | 0.9218 (2) | −0.23634 (13) | 0.59878 (8) | 0.0220 (3) | |
O12 | 0.58846 (18) | −0.25746 (9) | 0.66455 (6) | 0.0261 (3) | |
O13 | 0.35034 (18) | −0.38910 (10) | 0.62948 (6) | 0.0288 (3) | |
N21 | 0.8314 (2) | 0.02041 (11) | 0.66217 (7) | 0.0216 (3) | |
C21 | 0.5822 (2) | 0.12585 (12) | 0.64316 (8) | 0.0201 (3) | |
C22 | 0.5832 (2) | 0.10812 (12) | 0.57386 (8) | 0.0197 (3) | |
C23 | 0.4641 (2) | 0.15965 (13) | 0.53252 (8) | 0.0216 (3) | |
C24 | 0.3470 (2) | 0.22763 (13) | 0.55988 (9) | 0.0246 (4) | |
C25 | 0.3461 (3) | 0.24471 (13) | 0.62885 (9) | 0.0271 (4) | |
C26 | 0.4615 (2) | 0.19452 (13) | 0.66997 (8) | 0.0242 (4) | |
C27 | 0.7084 (2) | 0.07493 (12) | 0.68632 (8) | 0.0211 (3) | |
C131 | 0.2188 (3) | −0.46056 (15) | 0.61131 (10) | 0.0333 (4) | |
C231 | 0.3662 (3) | 0.19237 (15) | 0.42151 (9) | 0.0328 (4) | |
O22 | 0.69889 (18) | 0.04450 (9) | 0.54522 (6) | 0.0268 (3) | |
O23 | 0.47889 (17) | 0.13768 (9) | 0.46577 (5) | 0.0251 (3) | |
H1 | 1.1048 | −0.0919 | 0.6306 | 0.025* | |
H2 | 0.8969 | −0.0502 | 0.7482 | 0.025* | |
H3A | 1.1587 | 0.0761 | 0.6862 | 0.030* | |
H3B | 1.0472 | 0.1050 | 0.7513 | 0.030* | |
H4A | 1.1916 | −0.0178 | 0.8144 | 0.033* | |
H4B | 1.3397 | 0.0499 | 0.7796 | 0.033* | |
H5A | 1.4056 | −0.1244 | 0.7692 | 0.035* | |
H5B | 1.3912 | −0.0713 | 0.6979 | 0.035* | |
H6A | 1.2352 | −0.2228 | 0.6931 | 0.031* | |
H6B | 1.1203 | −0.1928 | 0.7573 | 0.031* | |
H12 | 0.6763 | −0.2217 | 0.6740 | 0.039* | |
H13A | 0.2647 | −0.5280 | 0.6188 | 0.050* | |
H13B | 0.1887 | −0.4524 | 0.5640 | 0.050* | |
H13C | 0.1127 | −0.4503 | 0.6386 | 0.050* | |
H14 | 0.4567 | −0.5019 | 0.5273 | 0.029* | |
H15 | 0.7263 | −0.4888 | 0.4699 | 0.032* | |
H16 | 0.9296 | −0.3667 | 0.4987 | 0.030* | |
H17 | 1.0245 | −0.2268 | 0.5722 | 0.026* | |
H22 | 0.7651 | 0.0201 | 0.5747 | 0.040* | |
H23A | 0.3899 | 0.2639 | 0.4262 | 0.049* | |
H23B | 0.2422 | 0.1789 | 0.4326 | 0.049* | |
H23C | 0.3894 | 0.1718 | 0.3754 | 0.049* | |
H24 | 0.2670 | 0.2628 | 0.5318 | 0.030* | |
H25 | 0.2652 | 0.2913 | 0.6474 | 0.032* | |
H26 | 0.4595 | 0.2064 | 0.7167 | 0.029* | |
H27 | 0.6990 | 0.0824 | 0.7334 | 0.025* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0219 (8) | 0.0205 (8) | 0.0189 (7) | −0.0023 (7) | −0.0006 (7) | 0.0006 (6) |
C2 | 0.0252 (8) | 0.0196 (8) | 0.0184 (7) | −0.0009 (7) | −0.0035 (7) | 0.0004 (6) |
C3 | 0.0295 (9) | 0.0193 (8) | 0.0271 (8) | −0.0011 (8) | −0.0052 (8) | −0.0010 (7) |
C4 | 0.0305 (10) | 0.0250 (9) | 0.0276 (8) | −0.0026 (8) | −0.0101 (8) | −0.0018 (7) |
C5 | 0.0247 (9) | 0.0267 (9) | 0.0356 (10) | 0.0018 (8) | −0.0103 (8) | −0.0019 (8) |
C6 | 0.0301 (10) | 0.0206 (8) | 0.0276 (8) | 0.0020 (8) | −0.0043 (8) | −0.0012 (7) |
N11 | 0.0248 (7) | 0.0200 (7) | 0.0204 (6) | −0.0020 (6) | −0.0019 (6) | −0.0011 (6) |
C11 | 0.0243 (8) | 0.0202 (8) | 0.0173 (7) | 0.0016 (7) | −0.0043 (7) | −0.0002 (6) |
C12 | 0.0273 (9) | 0.0193 (8) | 0.0163 (7) | 0.0026 (7) | −0.0028 (7) | −0.0020 (6) |
C13 | 0.0236 (8) | 0.0217 (8) | 0.0209 (7) | 0.0000 (7) | −0.0036 (7) | 0.0007 (6) |
C14 | 0.0282 (9) | 0.0209 (8) | 0.0245 (8) | 0.0013 (8) | −0.0097 (7) | −0.0032 (6) |
C15 | 0.0312 (9) | 0.0266 (9) | 0.0221 (8) | 0.0070 (8) | −0.0069 (8) | −0.0092 (7) |
C16 | 0.0249 (9) | 0.0309 (9) | 0.0203 (7) | 0.0050 (8) | −0.0015 (7) | −0.0042 (7) |
C17 | 0.0224 (8) | 0.0232 (8) | 0.0205 (8) | −0.0005 (7) | 0.0011 (7) | 0.0004 (6) |
O12 | 0.0288 (7) | 0.0280 (6) | 0.0216 (6) | −0.0068 (6) | 0.0048 (5) | −0.0088 (5) |
O13 | 0.0281 (7) | 0.0313 (7) | 0.0269 (6) | −0.0098 (6) | 0.0029 (5) | −0.0069 (5) |
N21 | 0.0229 (7) | 0.0213 (7) | 0.0207 (6) | −0.0006 (6) | −0.0021 (6) | 0.0012 (5) |
C21 | 0.0206 (8) | 0.0178 (7) | 0.0219 (8) | −0.0042 (7) | 0.0010 (6) | 0.0005 (6) |
C22 | 0.0194 (8) | 0.0172 (7) | 0.0224 (7) | −0.0004 (7) | 0.0026 (7) | −0.0013 (6) |
C23 | 0.0210 (8) | 0.0208 (8) | 0.0230 (7) | −0.0026 (7) | −0.0002 (7) | −0.0003 (6) |
C24 | 0.0213 (9) | 0.0226 (8) | 0.0299 (9) | 0.0016 (7) | −0.0021 (7) | 0.0029 (7) |
C25 | 0.0270 (9) | 0.0218 (8) | 0.0324 (9) | 0.0055 (8) | 0.0050 (8) | −0.0016 (7) |
C26 | 0.0274 (9) | 0.0219 (8) | 0.0233 (8) | −0.0015 (8) | 0.0054 (7) | −0.0019 (7) |
C27 | 0.0242 (8) | 0.0203 (8) | 0.0190 (7) | −0.0034 (7) | 0.0003 (7) | −0.0011 (6) |
C131 | 0.0320 (10) | 0.0359 (11) | 0.0320 (9) | −0.0114 (9) | −0.0041 (9) | −0.0027 (8) |
C231 | 0.0336 (10) | 0.0381 (10) | 0.0268 (9) | 0.0064 (9) | −0.0097 (8) | 0.0029 (8) |
O22 | 0.0269 (7) | 0.0326 (7) | 0.0210 (5) | 0.0116 (6) | −0.0010 (5) | −0.0027 (5) |
O23 | 0.0263 (6) | 0.0292 (6) | 0.0198 (5) | 0.0040 (6) | −0.0041 (5) | −0.0001 (5) |
C1—N11 | 1.463 (2) | C27—H27 | 0.95 |
C1—C6 | 1.527 (2) | C21—C26 | 1.403 (2) |
C1—C2 | 1.530 (2) | C21—C22 | 1.408 (2) |
C1—H1 | 1.00 | C22—O22 | 1.349 (2) |
N11—C17 | 1.281 (2) | C22—C23 | 1.405 (2) |
C17—C11 | 1.459 (2) | O22—H22 | 0.84 |
C17—H17 | 0.95 | C23—O23 | 1.3736 (19) |
C11—C12 | 1.400 (3) | C23—C24 | 1.383 (2) |
C11—C16 | 1.411 (2) | O23—C231 | 1.431 (2) |
C12—O12 | 1.3504 (19) | C231—H23A | 0.98 |
C12—C13 | 1.406 (2) | C231—H23B | 0.98 |
O12—H12 | 0.84 | C231—H23C | 0.98 |
C13—O13 | 1.368 (2) | C24—C25 | 1.400 (2) |
C13—C14 | 1.390 (2) | C24—H24 | 0.95 |
O13—C131 | 1.428 (2) | C25—C26 | 1.375 (3) |
C131—H13A | 0.98 | C25—H25 | 0.95 |
C131—H13B | 0.98 | C26—H26 | 0.95 |
C131—H13C | 0.98 | C3—C4 | 1.528 (3) |
C14—C15 | 1.400 (3) | C3—H3A | 0.99 |
C14—H14 | 0.95 | C3—H3B | 0.99 |
C15—C16 | 1.373 (3) | C4—C5 | 1.528 (3) |
C15—H15 | 0.95 | C4—H4A | 0.99 |
C16—H16 | 0.95 | C4—H4B | 0.99 |
C2—N21 | 1.465 (2) | C5—C6 | 1.529 (3) |
C2—C3 | 1.533 (2) | C5—H5A | 0.99 |
C2—H2 | 1.00 | C5—H5B | 0.99 |
N21—C27 | 1.278 (2) | C6—H6A | 0.99 |
C27—C21 | 1.457 (2) | C6—H6B | 0.99 |
N11—C1—C6 | 111.23 (13) | C22—C21—C27 | 120.15 (16) |
N11—C1—C2 | 108.74 (14) | O22—C22—C23 | 118.38 (14) |
C6—C1—C2 | 110.59 (13) | O22—C22—C21 | 121.96 (15) |
N11—C1—H1 | 108.7 | C23—C22—C21 | 119.64 (15) |
C6—C1—H1 | 108.7 | C22—O22—H22 | 109.5 |
C2—C1—H1 | 108.7 | O23—C23—C22 | 114.60 (15) |
C17—N11—C1 | 118.88 (15) | O23—C23—C24 | 125.37 (15) |
N11—C17—C11 | 121.58 (16) | C24—C23—C22 | 120.02 (15) |
N11—C17—H17 | 119.2 | C23—O23—C231 | 116.41 (14) |
C11—C17—H17 | 119.2 | O23—C231—H23A | 109.5 |
C12—C11—C16 | 119.36 (16) | O23—C231—H23B | 109.5 |
C12—C11—C17 | 120.21 (15) | H23A—C231—H23B | 109.5 |
C16—C11—C17 | 120.41 (16) | O23—C231—H23C | 109.5 |
O12—C12—C11 | 122.20 (16) | H23A—C231—H23C | 109.5 |
O12—C12—C13 | 117.81 (16) | H23B—C231—H23C | 109.5 |
C11—C12—C13 | 119.98 (15) | C23—C24—C25 | 120.10 (17) |
C12—O12—H12 | 109.5 | C23—C24—H24 | 120.0 |
O13—C13—C12 | 115.06 (14) | C25—C24—H24 | 120.0 |
O13—C13—C14 | 125.21 (16) | C26—C25—C24 | 120.53 (17) |
C14—C13—C12 | 119.72 (17) | C26—C25—H25 | 119.7 |
C13—O13—C131 | 116.97 (14) | C24—C25—H25 | 119.7 |
O13—C131—H13A | 109.5 | C25—C26—C21 | 120.26 (16) |
O13—C131—H13B | 109.5 | C25—C26—H26 | 119.9 |
H13A—C131—H13B | 109.5 | C21—C26—H26 | 119.9 |
O13—C131—H13C | 109.5 | C4—C3—C2 | 111.48 (14) |
H13A—C131—H13C | 109.5 | C4—C3—H3A | 109.3 |
H13B—C131—H13C | 109.5 | C2—C3—H3A | 109.3 |
C13—C14—C15 | 120.14 (17) | C4—C3—H3B | 109.3 |
C13—C14—H14 | 119.9 | C2—C3—H3B | 109.3 |
C15—C14—H14 | 119.9 | H3A—C3—H3B | 108.0 |
C16—C15—C14 | 120.51 (16) | C3—C4—C5 | 111.26 (14) |
C16—C15—H15 | 119.7 | C3—C4—H4A | 109.4 |
C14—C15—H15 | 119.7 | C5—C4—H4A | 109.4 |
C15—C16—C11 | 120.26 (17) | C3—C4—H4B | 109.4 |
C15—C16—H16 | 119.9 | C5—C4—H4B | 109.4 |
C11—C16—H16 | 119.9 | H4A—C4—H4B | 108.0 |
N21—C2—C1 | 109.15 (13) | C4—C5—C6 | 112.03 (16) |
N21—C2—C3 | 109.93 (13) | C4—C5—H5A | 109.2 |
C1—C2—C3 | 110.08 (15) | C6—C5—H5A | 109.2 |
N21—C2—H2 | 109.2 | C4—C5—H5B | 109.2 |
C1—C2—H2 | 109.2 | C6—C5—H5B | 109.2 |
C3—C2—H2 | 109.2 | H5A—C5—H5B | 107.9 |
C27—N21—C2 | 119.63 (14) | C1—C6—C5 | 110.43 (14) |
N21—C27—C21 | 121.30 (15) | C1—C6—H6A | 109.6 |
N21—C27—H27 | 119.4 | C5—C6—H6A | 109.6 |
C21—C27—H27 | 119.4 | C1—C6—H6B | 109.6 |
C26—C21—C22 | 119.45 (16) | C5—C6—H6B | 109.6 |
C26—C21—C27 | 120.38 (15) | H6A—C6—H6B | 108.1 |
C6—C1—N11—C17 | −91.25 (18) | C2—N21—C27—C21 | 177.82 (15) |
C2—C1—N11—C17 | 146.74 (15) | N21—C27—C21—C26 | −172.42 (16) |
C1—N11—C17—C11 | 178.86 (14) | N21—C27—C21—C22 | 6.1 (2) |
N11—C17—C11—C12 | 6.8 (2) | C26—C21—C22—O22 | 178.55 (15) |
N11—C17—C11—C16 | −171.31 (16) | C27—C21—C22—O22 | 0.0 (2) |
C16—C11—C12—O12 | 179.26 (15) | C26—C21—C22—C23 | 0.3 (2) |
C17—C11—C12—O12 | 1.1 (2) | C27—C21—C22—C23 | −178.29 (15) |
C16—C11—C12—C13 | 0.3 (2) | O22—C22—C23—O23 | 0.6 (2) |
C17—C11—C12—C13 | −177.84 (15) | C21—C22—C23—O23 | 178.98 (15) |
O12—C12—C13—O13 | 1.0 (2) | O22—C22—C23—C24 | −178.15 (15) |
C11—C12—C13—O13 | 179.97 (15) | C21—C22—C23—C24 | 0.2 (3) |
O12—C12—C13—C14 | −177.73 (15) | C24—C23—O23—C231 | 1.8 (2) |
C11—C12—C13—C14 | 1.2 (2) | C22—C23—O23—C231 | −176.88 (15) |
C14—C13—O13—C131 | −1.7 (2) | O23—C23—C24—C25 | −179.07 (17) |
C12—C13—O13—C131 | 179.67 (15) | C22—C23—C24—C25 | −0.4 (3) |
O13—C13—C14—C15 | −179.85 (16) | C23—C24—C25—C26 | 0.2 (3) |
C12—C13—C14—C15 | −1.3 (2) | C24—C25—C26—C21 | 0.3 (3) |
C13—C14—C15—C16 | −0.3 (3) | C22—C21—C26—C25 | −0.5 (3) |
C14—C15—C16—C11 | 1.9 (3) | C27—C21—C26—C25 | 178.04 (16) |
C12—C11—C16—C15 | −1.9 (2) | N21—C2—C3—C4 | −176.99 (14) |
C17—C11—C16—C15 | 176.25 (16) | C1—C2—C3—C4 | −56.73 (19) |
N11—C1—C2—N21 | −58.28 (17) | C2—C3—C4—C5 | 54.1 (2) |
C6—C1—C2—N21 | 179.32 (14) | C3—C4—C5—C6 | −53.5 (2) |
N11—C1—C2—C3 | −179.02 (13) | N11—C1—C6—C5 | −178.80 (14) |
C6—C1—C2—C3 | 58.58 (18) | C2—C1—C6—C5 | −57.87 (19) |
C1—C2—N21—C27 | 158.41 (15) | C4—C5—C6—C1 | 55.4 (2) |
C3—C2—N21—C27 | −80.76 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
O12—H12···N11 | 0.84 | 1.84 | 2.580 (2) | 147 |
O22—H22···N21 | 0.84 | 1.82 | 2.568 (2) | 147 |
C14—H14···O22i | 0.95 | 2.50 | 3.329 (2) | 146 |
C24—H24···O23ii | 0.95 | 2.55 | 3.356 (2) | 142 |
C26—H26···O12iii | 0.95 | 2.45 | 3.398 (2) | 172 |
Symmetry codes: (i) x−1/2, −y−1/2, −z+1; (ii) x−1/2, −y+1/2, −z+1; (iii) −x+1, y+1/2, −z+3/2. |
Experimental details
Crystal data | |
Chemical formula | C22H26N2O4 |
Mr | 382.45 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 120 |
a, b, c (Å) | 7.5558 (2), 13.4054 (1), 20.0304 (3) |
V (Å3) | 2028.85 (6) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.32 × 0.25 × 0.08 |
Data collection | |
Diffractometer | Nonius KappaCCD diffractometer |
Absorption correction | Multi-scan DENZO–SMN (Otwinowski & Minor, 1997) |
Tmin, Tmax | 0.962, 0.994 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 27432, 2642, 2484 |
Rint | 0.071 |
(sin θ/λ)max (Å−1) | 0.648 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.035, 0.084, 1.08 |
No. of reflections | 2646 |
No. of parameters | 257 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.16, −0.22 |
Computer programs: KappaCCD Server Software (Nonius, 1997), DENZO–SMN (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXL97 (Sheldrick, 1997) and PRPKAPPA (Ferguson, 1999).
O13—C13—C12 | 115.06 (14) | O23—C23—C22 | 114.60 (15) |
O13—C13—C14 | 125.21 (16) | O23—C23—C24 | 125.37 (15) |
C2—C1—N11—C17 | 146.74 (15) | C1—C2—N21—C27 | 158.41 (15) |
C1—N11—C17—C11 | 178.86 (14) | C2—N21—C27—C21 | 177.82 (15) |
N11—C17—C11—C12 | 6.8 (2) | N21—C27—C21—C22 | 6.1 (2) |
C12—C13—O13—C131 | 179.67 (15) | C22—C23—O23—C231 | −176.88 (15) |
D—H···A | D—H | H···A | D···A | D—H···A |
O12—H12···N11 | 0.84 | 1.84 | 2.580 (2) | 147 |
O22—H22···N21 | 0.84 | 1.82 | 2.568 (2) | 147 |
C14—H14···O22i | 0.95 | 2.50 | 3.329 (2) | 146 |
C24—H24···O23ii | 0.95 | 2.55 | 3.356 (2) | 142 |
C26—H26···O12iii | 0.95 | 2.45 | 3.398 (2) | 172 |
Symmetry codes: (i) x−1/2, −y−1/2, −z+1; (ii) x−1/2, −y+1/2, −z+1; (iii) −x+1, y+1/2, −z+3/2. |
Chiral Schiff base complexes have been used as efficient catalysts for Michael reactions (Jha & Joshi, 2001), for epoxidation (Larrow & Jacobson, 1994) and for aziridination (Liang et al., 2002) of alkenes. Furthermore the N atoms of azomethine groups in metal complexes can act as hydrogen-bond acceptors, and it has been proposed that this interaction can account for some of the antibacterial and antifungal activities of ruthenium complexes (Ramesh & Sivagamasundari, 2003). The title compound, (I), was prepared as a forerunner to the synthesis and investigation of chiral ruthenium Schiff base complexes, and the present structural investigation was undertaken in order to assign unambiguously the structure and the hydrogen bonding.
The cyclohexane moiety adopts the usual chain conformation, with the two substituents in equatorial sites. There are two intramolecular O—H···N hydrogen bonds (Fig. 1), each forming an S(6) motif (Bernstein et al., 1995), and these undoubtedly play a part in controlling the overall molecular conformation. This conformation is close to C2 symmetry, but examination of the key torsion angles (Table 1) confirms the absence of exact twofold rotational symmetry. The bond distances show no unusual features, and the exocyclic C—C—O angles at C13 and C23 show the usual pattern (Seip & Seip, 1973; Ferguson et al., 1996; Patterson et al., 1998; Abonia et al., 2003)
The absence of twofold rotational symmetry is confirmed by the pattern and dimensions of the soft (Desiraju & Steiner, 1999) C—H···O hydrogen bonds (Table 2), where one phenyl ring, C11–C16, provides only one donor and one acceptor, while the other ring, C21–C26, provides two donors and two acceptors. These three hydrogen bonds serve to link the molecules into a continuous three-dimensional framework, whose description can be simplified by the use of the substructure approach (Gregson et al., 2000).
Atom C14 in the molecule at (x, y, z) acts as a hydrogen-bond donor to phenol atom O22 in the molecule at (−0.5 + x, −0.5 − y, 1 − z), while atom C14 at (−0.5 + x, −0.5 − y, 1 − z) in turn acts as a donor to atom O22 at (−1 + x, y, z), so producing a C(14) chain running parallel to the [100] direction and generated by the 21 screw axis along (x, −0.25, 1/2). At the same time, atom C24 at (x, y, z) acts as a donor to methoxyl atom O23 at (−0.5 + x, 0.5 − y, 1 − z), so producing a C(4) chain around the 21 screw axis along (x, 1/4, 1/2). These two chain motifs combine to produce a (001) sheet in the form of a (4,4) net (Batten & Robson, 1998) built from a single type of R44(38) ring (Fig. 2). Two sheets of this type pass through each unit cell, in the domains 0.23 < z < 0.77 and 0.73 < z < 1.27, and these sheets are linked into a single framework by the third of the C—H···O hydrogen bonds.
Atom C26 in the molecule at (x, y, z) acts as a hydrogen bond donor to phenol atom O12 in the molecule at (1 − x, 0.5 + y, 1.5 − z), and propagation of this interaction produces a C(12) chain running parallel to the [010] direction and generated by the 21 screw axis along (1/2, y, 3/4) (Fig. 3). The molecules at (x, y, z) and (1 − x, 0.5 + y, 1.5 − z) lie, respectively, in the 0.23 < z < 0.77 and 0.73 < z < 1.27 sheets. Similarly, atom C26 in the molecule at (−0.5 + x, −0.5 − y, 1 − z), which also lies in the 0.23 < z < 0.77 sheet, acts as a hydrogen-bond donor to atom O12 in the molecule at (0.5 − x, −1 − y, −0.5 + z), which lies in the −0.27 < z < 0.27 sheet. Hence, this hydrogen bond links each (001) sheet to the two neighbouring sheets, so forming a single continuous framework.