| Literature DB >> 23476426 |
Sema Oztürk Yildirim1, Ray J Butcher, Miyase Gözde Gündüz, Ahmed El-Khouly, Rahime Simşek, Cihat Safak.
Abstract
In the title mol-ecule, C24H28N2O3, theEntities:
Year: 2012 PMID: 23476426 PMCID: PMC3588325 DOI: 10.1107/S1600536812047976
Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN: 1600-5368
| C24H28N2O3 | |
| Monoclinic, | Cu |
| Hall symbol: -P 2ybc | Cell parameters from 3252 reflections |
| θ = 3.7–75.7° | |
| µ = 0.65 mm−1 | |
| β = 106.806 (2)° | Block, colorless |
| 0.55 × 0.40 × 0.35 mm | |
| Agilent Xcalibur (Ruby, Gemini) diffractometer | 4246 independent reflections |
| Radiation source: Enhance (Cu) X-ray Source | 3533 reflections with |
| Graphite monochromator | |
| Detector resolution: 10.5081 pixels mm-1 | θmax = 75.9°, θmin = 5.1° |
| ω scans | |
| Absorption correction: multi-scan [ | |
| 8035 measured reflections |
| Refinement on | Primary atom site location: structure-invariant direct methods |
| Least-squares matrix: full | Secondary atom site location: difference Fourier map |
| Hydrogen site location: inferred from neighbouring sites | |
| H atoms treated by a mixture of independent and constrained refinement | |
| 4246 reflections | (Δ/σ)max = 0.001 |
| 271 parameters | Δρmax = 0.27 e Å−3 |
| 0 restraints | Δρmin = −0.23 e Å−3 |
| Experimental. Absorption correction: CrysAlis RED, (Agilent, 2011) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. (Clark & Reid, 1995). |
| Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
| Refinement. Refinement of |
| O1 | 0.80036 (6) | 0.10674 (11) | 0.14843 (8) | 0.0291 (2) | |
| O2 | 0.50682 (7) | 0.45404 (15) | 0.20829 (11) | 0.0444 (3) | |
| O3 | 0.53584 (6) | 0.31811 (11) | 0.08329 (9) | 0.0281 (2) | |
| N1 | 0.74838 (7) | 0.40267 (13) | 0.41035 (10) | 0.0250 (3) | |
| N2 | 0.70297 (7) | 0.49919 (13) | −0.07455 (10) | 0.0254 (3) | |
| C1 | 0.79738 (8) | 0.31973 (14) | 0.37441 (11) | 0.0235 (3) | |
| C2 | 0.87530 (9) | 0.28770 (16) | 0.46042 (12) | 0.0289 (3) | |
| H2A | 0.8662 | 0.2185 | 0.5116 | 0.035* | |
| H2B | 0.8952 | 0.3668 | 0.5066 | 0.035* | |
| C3 | 0.93922 (9) | 0.24060 (16) | 0.40645 (12) | 0.0301 (3) | |
| C4 | 0.90135 (9) | 0.13072 (16) | 0.32375 (13) | 0.0312 (3) | |
| H4A | 0.9397 | 0.1037 | 0.2825 | 0.037* | |
| H4B | 0.8921 | 0.0540 | 0.3675 | 0.037* | |
| C5 | 0.82268 (8) | 0.16811 (14) | 0.23802 (11) | 0.0240 (3) | |
| C6 | 0.77439 (8) | 0.26933 (14) | 0.26782 (11) | 0.0221 (3) | |
| C7 | 0.69728 (8) | 0.31300 (14) | 0.18198 (11) | 0.0218 (3) | |
| H7A | 0.6704 | 0.2333 | 0.1409 | 0.026* | |
| C8 | 0.64109 (8) | 0.37442 (14) | 0.24284 (11) | 0.0232 (3) | |
| C9 | 0.66851 (8) | 0.42081 (14) | 0.34996 (12) | 0.0242 (3) | |
| C10 | 0.71174 (8) | 0.40744 (14) | 0.09521 (11) | 0.0223 (3) | |
| C11 | 0.75097 (8) | 0.53337 (14) | 0.11377 (12) | 0.0233 (3) | |
| C12 | 0.78991 (8) | 0.60792 (15) | 0.20974 (12) | 0.0269 (3) | |
| H12A | 0.7970 | 0.5736 | 0.2835 | 0.032* | |
| C13 | 0.81773 (9) | 0.73194 (16) | 0.19525 (13) | 0.0308 (3) | |
| H13A | 0.8438 | 0.7827 | 0.2599 | 0.037* | |
| C14 | 0.80824 (9) | 0.78432 (16) | 0.08691 (14) | 0.0317 (3) | |
| H14A | 0.8277 | 0.8700 | 0.0796 | 0.038* | |
| C15 | 0.77111 (9) | 0.71327 (16) | −0.00918 (13) | 0.0297 (3) | |
| H15A | 0.7647 | 0.7485 | −0.0825 | 0.036* | |
| C16 | 0.74337 (8) | 0.58779 (15) | 0.00536 (12) | 0.0249 (3) | |
| C17 | 0.68333 (8) | 0.39281 (14) | −0.01990 (11) | 0.0246 (3) | |
| H17A | 0.6540 | 0.3189 | −0.0568 | 0.029* | |
| C18 | 0.55550 (8) | 0.38803 (15) | 0.18007 (12) | 0.0266 (3) | |
| C19 | 0.45226 (9) | 0.32978 (17) | 0.01690 (13) | 0.0317 (3) | |
| H19A | 0.4382 | 0.4232 | 0.0000 | 0.038* | |
| H19B | 0.4171 | 0.2937 | 0.0598 | 0.038* | |
| C20 | 0.44107 (10) | 0.2548 (2) | −0.09068 (15) | 0.0436 (4) | |
| H20A | 0.3850 | 0.2606 | −0.1364 | 0.065* | |
| H20B | 0.4553 | 0.1626 | −0.0731 | 0.065* | |
| H20C | 0.4755 | 0.2920 | −0.1330 | 0.065* | |
| C21 | 0.62218 (9) | 0.49093 (17) | 0.41785 (13) | 0.0313 (3) | |
| H21A | 0.5844 | 0.5522 | 0.3688 | 0.047* | |
| H21B | 0.6592 | 0.5396 | 0.4796 | 0.047* | |
| H21C | 0.5927 | 0.4267 | 0.4494 | 0.047* | |
| C22 | 1.01088 (10) | 0.1881 (2) | 0.49980 (15) | 0.0404 (4) | |
| H22A | 1.0511 | 0.1540 | 0.4659 | 0.061* | |
| H22B | 0.9931 | 0.1174 | 0.5408 | 0.061* | |
| H22C | 1.0342 | 0.2592 | 0.5525 | 0.061* | |
| C23 | 0.96694 (10) | 0.35270 (19) | 0.34418 (15) | 0.0390 (4) | |
| H23A | 1.0071 | 0.3197 | 0.3095 | 0.058* | |
| H23B | 0.9904 | 0.4227 | 0.3980 | 0.058* | |
| H23C | 0.9211 | 0.3874 | 0.2852 | 0.058* | |
| C24 | 0.67642 (9) | 0.52313 (17) | −0.19626 (12) | 0.0307 (3) | |
| H24A | 0.6508 | 0.4438 | −0.2354 | 0.046* | |
| H24B | 0.7226 | 0.5459 | −0.2225 | 0.046* | |
| H24C | 0.6380 | 0.5958 | −0.2126 | 0.046* | |
| H1N | 0.7596 (11) | 0.414 (2) | 0.4823 (17) | 0.033 (5)* |
| O1 | 0.0361 (5) | 0.0295 (6) | 0.0207 (5) | 0.0038 (4) | 0.0064 (4) | −0.0004 (4) |
| O2 | 0.0284 (6) | 0.0622 (9) | 0.0387 (6) | 0.0099 (6) | 0.0033 (5) | −0.0156 (6) |
| O3 | 0.0226 (5) | 0.0304 (5) | 0.0266 (5) | 0.0016 (4) | −0.0001 (4) | −0.0026 (4) |
| N1 | 0.0275 (6) | 0.0286 (6) | 0.0166 (5) | 0.0006 (5) | 0.0029 (4) | −0.0013 (5) |
| N2 | 0.0297 (6) | 0.0276 (6) | 0.0183 (5) | 0.0048 (5) | 0.0058 (4) | 0.0028 (5) |
| C1 | 0.0251 (6) | 0.0241 (7) | 0.0198 (6) | −0.0004 (5) | 0.0040 (5) | 0.0022 (5) |
| C2 | 0.0279 (7) | 0.0352 (8) | 0.0196 (6) | 0.0020 (6) | 0.0007 (5) | 0.0001 (6) |
| C3 | 0.0255 (7) | 0.0353 (8) | 0.0253 (7) | 0.0036 (6) | 0.0007 (6) | 0.0006 (6) |
| C4 | 0.0301 (7) | 0.0331 (8) | 0.0273 (7) | 0.0089 (6) | 0.0034 (6) | 0.0000 (6) |
| C5 | 0.0277 (7) | 0.0246 (7) | 0.0193 (6) | 0.0008 (5) | 0.0060 (5) | 0.0028 (5) |
| C6 | 0.0231 (6) | 0.0229 (6) | 0.0187 (6) | 0.0008 (5) | 0.0033 (5) | 0.0023 (5) |
| C7 | 0.0238 (6) | 0.0218 (6) | 0.0174 (6) | −0.0001 (5) | 0.0020 (5) | 0.0005 (5) |
| C8 | 0.0246 (7) | 0.0232 (7) | 0.0209 (6) | 0.0010 (5) | 0.0050 (5) | 0.0025 (5) |
| C9 | 0.0261 (7) | 0.0233 (7) | 0.0230 (6) | −0.0003 (5) | 0.0064 (5) | 0.0015 (5) |
| C10 | 0.0234 (6) | 0.0226 (7) | 0.0192 (6) | 0.0032 (5) | 0.0036 (5) | 0.0003 (5) |
| C11 | 0.0234 (6) | 0.0236 (7) | 0.0226 (6) | 0.0037 (5) | 0.0063 (5) | 0.0026 (5) |
| C12 | 0.0271 (7) | 0.0280 (7) | 0.0242 (6) | 0.0011 (6) | 0.0051 (5) | 0.0000 (6) |
| C13 | 0.0302 (7) | 0.0283 (8) | 0.0320 (8) | −0.0017 (6) | 0.0062 (6) | −0.0036 (6) |
| C14 | 0.0301 (7) | 0.0243 (7) | 0.0411 (9) | −0.0003 (6) | 0.0113 (6) | 0.0050 (6) |
| C15 | 0.0302 (7) | 0.0300 (8) | 0.0303 (7) | 0.0052 (6) | 0.0113 (6) | 0.0084 (6) |
| C16 | 0.0237 (6) | 0.0272 (7) | 0.0239 (7) | 0.0053 (5) | 0.0070 (5) | 0.0026 (6) |
| C17 | 0.0273 (7) | 0.0239 (7) | 0.0209 (6) | 0.0036 (5) | 0.0045 (5) | 0.0001 (5) |
| C18 | 0.0255 (7) | 0.0286 (7) | 0.0244 (6) | −0.0002 (6) | 0.0052 (5) | 0.0013 (6) |
| C19 | 0.0220 (7) | 0.0335 (8) | 0.0334 (8) | 0.0026 (6) | −0.0019 (6) | −0.0030 (6) |
| C20 | 0.0343 (8) | 0.0480 (10) | 0.0385 (9) | 0.0068 (8) | −0.0056 (7) | −0.0127 (8) |
| C21 | 0.0309 (7) | 0.0358 (8) | 0.0267 (7) | 0.0018 (6) | 0.0075 (6) | −0.0048 (6) |
| C22 | 0.0294 (8) | 0.0494 (10) | 0.0349 (8) | 0.0077 (7) | −0.0025 (6) | 0.0011 (8) |
| C23 | 0.0295 (7) | 0.0459 (10) | 0.0399 (9) | −0.0019 (7) | 0.0074 (6) | 0.0033 (8) |
| C24 | 0.0369 (8) | 0.0364 (8) | 0.0186 (6) | 0.0082 (6) | 0.0078 (6) | 0.0047 (6) |
| O1—C5 | 1.2317 (18) | C10—C11 | 1.441 (2) |
| O2—C18 | 1.2115 (19) | C11—C12 | 1.406 (2) |
| O3—C18 | 1.3475 (18) | C11—C16 | 1.4191 (19) |
| O3—C19 | 1.4578 (16) | C12—C13 | 1.384 (2) |
| N1—C1 | 1.3648 (19) | C12—H12A | 0.9500 |
| N1—C9 | 1.3910 (18) | C13—C14 | 1.405 (2) |
| N1—H1N | 0.86 (2) | C13—H13A | 0.9500 |
| N2—C17 | 1.3716 (19) | C14—C15 | 1.381 (2) |
| N2—C16 | 1.3724 (19) | C14—H14A | 0.9500 |
| N2—C24 | 1.4594 (17) | C15—C16 | 1.397 (2) |
| C1—C6 | 1.3606 (19) | C15—H15A | 0.9500 |
| C1—C2 | 1.5002 (18) | C17—H17A | 0.9500 |
| C2—C3 | 1.533 (2) | C19—C20 | 1.495 (2) |
| C2—H2A | 0.9900 | C19—H19A | 0.9900 |
| C2—H2B | 0.9900 | C19—H19B | 0.9900 |
| C3—C4 | 1.531 (2) | C20—H20A | 0.9800 |
| C3—C23 | 1.531 (2) | C20—H20B | 0.9800 |
| C3—C22 | 1.532 (2) | C20—H20C | 0.9800 |
| C4—C5 | 1.5207 (19) | C21—H21A | 0.9800 |
| C4—H4A | 0.9900 | C21—H21B | 0.9800 |
| C4—H4B | 0.9900 | C21—H21C | 0.9800 |
| C5—C6 | 1.446 (2) | C22—H22A | 0.9800 |
| C6—C7 | 1.5197 (17) | C22—H22B | 0.9800 |
| C7—C10 | 1.5146 (19) | C22—H22C | 0.9800 |
| C7—C8 | 1.5315 (19) | C23—H23A | 0.9800 |
| C7—H7A | 1.0000 | C23—H23B | 0.9800 |
| C8—C9 | 1.355 (2) | C23—H23C | 0.9800 |
| C8—C18 | 1.4781 (19) | C24—H24A | 0.9800 |
| C9—C21 | 1.503 (2) | C24—H24B | 0.9800 |
| C10—C17 | 1.3713 (18) | C24—H24C | 0.9800 |
| C18—O3—C19 | 114.36 (11) | C12—C13—C14 | 121.39 (14) |
| C1—N1—C9 | 122.27 (12) | C12—C13—H13A | 119.3 |
| C1—N1—H1N | 116.4 (13) | C14—C13—H13A | 119.3 |
| C9—N1—H1N | 115.4 (13) | C15—C14—C13 | 121.05 (14) |
| C17—N2—C16 | 108.41 (12) | C15—C14—H14A | 119.5 |
| C17—N2—C24 | 126.04 (13) | C13—C14—H14A | 119.5 |
| C16—N2—C24 | 125.07 (13) | C14—C15—C16 | 117.61 (14) |
| C6—C1—N1 | 120.71 (12) | C14—C15—H15A | 121.2 |
| C6—C1—C2 | 123.79 (13) | C16—C15—H15A | 121.2 |
| N1—C1—C2 | 115.48 (12) | N2—C16—C15 | 129.41 (13) |
| C1—C2—C3 | 112.70 (12) | N2—C16—C11 | 108.03 (13) |
| C1—C2—H2A | 109.1 | C15—C16—C11 | 122.51 (14) |
| C3—C2—H2A | 109.1 | C10—C17—N2 | 110.91 (13) |
| C1—C2—H2B | 109.1 | C10—C17—H17A | 124.5 |
| C3—C2—H2B | 109.1 | N2—C17—H17A | 124.5 |
| H2A—C2—H2B | 107.8 | O2—C18—O3 | 121.90 (13) |
| C4—C3—C23 | 110.43 (13) | O2—C18—C8 | 126.06 (14) |
| C4—C3—C22 | 110.36 (14) | O3—C18—C8 | 112.03 (12) |
| C23—C3—C22 | 109.28 (14) | O3—C19—C20 | 108.07 (12) |
| C4—C3—C2 | 106.87 (12) | O3—C19—H19A | 110.1 |
| C23—C3—C2 | 111.12 (14) | C20—C19—H19A | 110.1 |
| C22—C3—C2 | 108.75 (13) | O3—C19—H19B | 110.1 |
| C5—C4—C3 | 114.23 (13) | C20—C19—H19B | 110.1 |
| C5—C4—H4A | 108.7 | H19A—C19—H19B | 108.4 |
| C3—C4—H4A | 108.7 | C19—C20—H20A | 109.5 |
| C5—C4—H4B | 108.7 | C19—C20—H20B | 109.5 |
| C3—C4—H4B | 108.7 | H20A—C20—H20B | 109.5 |
| H4A—C4—H4B | 107.6 | C19—C20—H20C | 109.5 |
| O1—C5—C6 | 122.29 (13) | H20A—C20—H20C | 109.5 |
| O1—C5—C4 | 119.05 (13) | H20B—C20—H20C | 109.5 |
| C6—C5—C4 | 118.54 (12) | C9—C21—H21A | 109.5 |
| C1—C6—C5 | 118.99 (12) | C9—C21—H21B | 109.5 |
| C1—C6—C7 | 121.21 (13) | H21A—C21—H21B | 109.5 |
| C5—C6—C7 | 119.73 (12) | C9—C21—H21C | 109.5 |
| C10—C7—C6 | 112.57 (11) | H21A—C21—H21C | 109.5 |
| C10—C7—C8 | 110.43 (11) | H21B—C21—H21C | 109.5 |
| C6—C7—C8 | 109.99 (11) | C3—C22—H22A | 109.5 |
| C10—C7—H7A | 107.9 | C3—C22—H22B | 109.5 |
| C6—C7—H7A | 107.9 | H22A—C22—H22B | 109.5 |
| C8—C7—H7A | 107.9 | C3—C22—H22C | 109.5 |
| C9—C8—C18 | 119.84 (13) | H22A—C22—H22C | 109.5 |
| C9—C8—C7 | 121.71 (12) | H22B—C22—H22C | 109.5 |
| C18—C8—C7 | 118.39 (12) | C3—C23—H23A | 109.5 |
| C8—C9—N1 | 119.58 (13) | C3—C23—H23B | 109.5 |
| C8—C9—C21 | 127.93 (13) | H23A—C23—H23B | 109.5 |
| N1—C9—C21 | 112.48 (12) | C3—C23—H23C | 109.5 |
| C17—C10—C11 | 105.93 (12) | H23A—C23—H23C | 109.5 |
| C17—C10—C7 | 125.43 (13) | H23B—C23—H23C | 109.5 |
| C11—C10—C7 | 128.46 (12) | N2—C24—H24A | 109.5 |
| C12—C11—C16 | 118.31 (13) | N2—C24—H24B | 109.5 |
| C12—C11—C10 | 134.96 (13) | H24A—C24—H24B | 109.5 |
| C16—C11—C10 | 106.70 (12) | N2—C24—H24C | 109.5 |
| C13—C12—C11 | 119.12 (14) | H24A—C24—H24C | 109.5 |
| C13—C12—H12A | 120.4 | H24B—C24—H24C | 109.5 |
| C11—C12—H12A | 120.4 | ||
| C9—N1—C1—C6 | 12.1 (2) | C6—C7—C10—C17 | 126.79 (14) |
| C9—N1—C1—C2 | −166.63 (13) | C8—C7—C10—C17 | −109.86 (15) |
| C6—C1—C2—C3 | 23.2 (2) | C6—C7—C10—C11 | −58.89 (18) |
| N1—C1—C2—C3 | −158.12 (13) | C8—C7—C10—C11 | 64.47 (17) |
| C1—C2—C3—C4 | −51.15 (17) | C17—C10—C11—C12 | 177.98 (16) |
| C1—C2—C3—C23 | 69.39 (17) | C7—C10—C11—C12 | 2.8 (3) |
| C1—C2—C3—C22 | −170.29 (14) | C17—C10—C11—C16 | −0.02 (15) |
| C23—C3—C4—C5 | −67.55 (17) | C7—C10—C11—C16 | −175.22 (13) |
| C22—C3—C4—C5 | 171.52 (13) | C16—C11—C12—C13 | 1.4 (2) |
| C2—C3—C4—C5 | 53.44 (17) | C10—C11—C12—C13 | −176.46 (15) |
| C3—C4—C5—O1 | 157.14 (14) | C11—C12—C13—C14 | −0.3 (2) |
| C3—C4—C5—C6 | −26.6 (2) | C12—C13—C14—C15 | −0.4 (2) |
| N1—C1—C6—C5 | −171.47 (13) | C13—C14—C15—C16 | 0.1 (2) |
| C2—C1—C6—C5 | 7.2 (2) | C17—N2—C16—C15 | −175.84 (14) |
| N1—C1—C6—C7 | 5.7 (2) | C24—N2—C16—C15 | −3.4 (2) |
| C2—C1—C6—C7 | −175.67 (13) | C17—N2—C16—C11 | 1.48 (15) |
| O1—C5—C6—C1 | 170.63 (13) | C24—N2—C16—C11 | 173.94 (13) |
| C4—C5—C6—C1 | −5.5 (2) | C14—C15—C16—N2 | 178.00 (14) |
| O1—C5—C6—C7 | −6.6 (2) | C14—C15—C16—C11 | 1.0 (2) |
| C4—C5—C6—C7 | 177.32 (13) | C12—C11—C16—N2 | −179.29 (12) |
| C1—C6—C7—C10 | 103.36 (15) | C10—C11—C16—N2 | −0.90 (15) |
| C5—C6—C7—C10 | −79.50 (16) | C12—C11—C16—C15 | −1.7 (2) |
| C1—C6—C7—C8 | −20.24 (19) | C10—C11—C16—C15 | 176.65 (13) |
| C5—C6—C7—C8 | 156.90 (12) | C11—C10—C17—N2 | 0.95 (16) |
| C10—C7—C8—C9 | −104.62 (15) | C7—C10—C17—N2 | 176.33 (12) |
| C6—C7—C8—C9 | 20.22 (19) | C16—N2—C17—C10 | −1.55 (16) |
| C10—C7—C8—C18 | 72.63 (16) | C24—N2—C17—C10 | −173.91 (13) |
| C6—C7—C8—C18 | −162.53 (12) | C19—O3—C18—O2 | 0.3 (2) |
| C18—C8—C9—N1 | 177.22 (13) | C19—O3—C18—C8 | −178.99 (12) |
| C7—C8—C9—N1 | −5.6 (2) | C9—C8—C18—O2 | 11.2 (2) |
| C18—C8—C9—C21 | −1.5 (2) | C7—C8—C18—O2 | −166.16 (16) |
| C7—C8—C9—C21 | 175.75 (14) | C9—C8—C18—O3 | −169.60 (13) |
| C1—N1—C9—C8 | −12.1 (2) | C7—C8—C18—O3 | 13.10 (18) |
| C1—N1—C9—C21 | 166.76 (13) | C18—O3—C19—C20 | 176.22 (14) |
| H··· | ||||
| C21—H21 | 0.98 | 2.28 | 2.8073 (19) | 113 |
| N1—H1 | 0.86 (2) | 1.98 (2) | 2.8161 (15) | 163.9 (19) |
| C24—H24 | 0.98 | 2.60 | 3.1693 (19) | 118 |
Hydrogen-bond geometry (Å, °)
|
|
| H⋯ |
|
|
|---|---|---|---|---|
| C21—H21 | 0.98 | 2.28 | 2.8073 (19) | 113 |
| N1—H1 | 0.86 (2) | 1.98 (2) | 2.8161 (15) | 163.9 (19) |
| C24—H24 | 0.98 | 2.60 | 3.1693 (19) | 118 |
Symmetry codes: (i) ; (ii) .