Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807053846/hg2335sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807053846/hg2335Isup2.hkl |
CCDC reference: 672809
Key indicators
- Single-crystal X-ray study
- T = 200 K
- Mean (C-C) = 0.002 Å
- R factor = 0.048
- wR factor = 0.142
- Data-to-parameter ratio = 27.2
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.98 PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.30 PLAT230_ALERT_2_C Hirshfeld Test Diff for N1 - C1 .. 5.66 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C23 - C24 .. 6.27 su
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 0.978 Tmax scaled 0.978 Tmin scaled 0.948 PLAT793_ALERT_1_G Check the Absolute Configuration of C2 = ... R PLAT793_ALERT_1_G Check the Absolute Configuration of C3 = ... S PLAT793_ALERT_1_G Check the Absolute Configuration of C6 = ... S
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 4 ALERT level G = General alerts; check 3 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 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
H atoms were positioned geometrically and allowed to ride on their parent atoms with C—H = 0.93–0.98 Å and Uiso = 1.2Ueq(C).
Data collection: CrysAlis CCD (Oxford Diffraction, 2007); cell refinement: CrysAlis CCD (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2003).
C25H23NO2 | F(000) = 784 |
Mr = 369.44 | Dx = 1.208 Mg m−3 |
Monoclinic, P21/c | Melting point: 355.5 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 10.5355 (3) Å | Cell parameters from 7426 reflections |
b = 9.3464 (2) Å | θ = 4.4–32.4° |
c = 21.0493 (5) Å | µ = 0.08 mm−1 |
β = 101.520 (3)° | T = 200 K |
V = 2030.95 (9) Å3 | Prism, colourless |
Z = 4 | 0.41 × 0.37 × 0.29 mm |
Oxford Diffraction Gemini diffractometer | 6871 independent reflections |
Radiation source: fine-focus sealed tube | 3596 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.041 |
Detector resolution: 10.5081 pixels mm-1 | θmax = 32.5°, θmin = 4.5° |
phi and ω scans | h = −15→15 |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007) | k = −14→14 |
Tmin = 0.969, Tmax = 1.000 | l = −28→31 |
29482 measured reflections |
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)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.142 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0708P)2] where P = (Fo2 + 2Fc2)/3 |
6871 reflections | (Δ/σ)max < 0.001 |
253 parameters | Δρmax = 0.47 e Å−3 |
0 restraints | Δρmin = −0.21 e Å−3 |
C25H23NO2 | V = 2030.95 (9) Å3 |
Mr = 369.44 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 10.5355 (3) Å | µ = 0.08 mm−1 |
b = 9.3464 (2) Å | T = 200 K |
c = 21.0493 (5) Å | 0.41 × 0.37 × 0.29 mm |
β = 101.520 (3)° |
Oxford Diffraction Gemini diffractometer | 6871 independent reflections |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007) | 3596 reflections with I > 2σ(I) |
Tmin = 0.969, Tmax = 1.000 | Rint = 0.041 |
29482 measured reflections |
R[F2 > 2σ(F2)] = 0.048 | 0 restraints |
wR(F2) = 0.142 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.47 e Å−3 |
6871 reflections | Δρmin = −0.21 e Å−3 |
253 parameters |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.54289 (11) | 0.47782 (12) | 0.30209 (5) | 0.0663 (4) | |
O4 | 0.38017 (9) | −0.07286 (10) | 0.42653 (5) | 0.0494 (3) | |
N1 | 0.41809 (9) | 0.29206 (10) | 0.32395 (5) | 0.0291 (3) | |
C1 | 0.46406 (13) | 0.38370 (16) | 0.28479 (7) | 0.0476 (5) | |
C2 | 0.47899 (11) | 0.28447 (12) | 0.39350 (5) | 0.0272 (3) | |
C3 | 0.51165 (10) | 0.12848 (12) | 0.41163 (5) | 0.0280 (3) | |
C4 | 0.39016 (11) | 0.03862 (13) | 0.39836 (6) | 0.0315 (3) | |
C5 | 0.28084 (11) | 0.09412 (13) | 0.34687 (6) | 0.0322 (3) | |
C6 | 0.32664 (11) | 0.17928 (13) | 0.29375 (5) | 0.0288 (3) | |
C13 | 0.61104 (12) | 0.06259 (13) | 0.37492 (6) | 0.0356 (4) | |
C21 | 0.39739 (10) | 0.35930 (12) | 0.43612 (6) | 0.0290 (3) | |
C22 | 0.34968 (13) | 0.49578 (14) | 0.41958 (7) | 0.0408 (4) | |
C23 | 0.27833 (13) | 0.56808 (15) | 0.45821 (8) | 0.0493 (5) | |
C24 | 0.25355 (13) | 0.50590 (16) | 0.51372 (8) | 0.0494 (5) | |
C25 | 0.30142 (14) | 0.37287 (17) | 0.53101 (7) | 0.0504 (5) | |
C26 | 0.37350 (12) | 0.29960 (14) | 0.49291 (6) | 0.0391 (4) | |
C31 | 0.74256 (11) | 0.13162 (13) | 0.38979 (6) | 0.0348 (4) | |
C32 | 0.78627 (14) | 0.21533 (17) | 0.34426 (8) | 0.0521 (5) | |
C33 | 0.90858 (16) | 0.27711 (19) | 0.35832 (10) | 0.0648 (7) | |
C34 | 0.98829 (15) | 0.25635 (17) | 0.41737 (10) | 0.0599 (6) | |
C35 | 0.94666 (14) | 0.17417 (17) | 0.46316 (8) | 0.0538 (5) | |
C36 | 0.82463 (12) | 0.11224 (15) | 0.44955 (7) | 0.0417 (4) | |
C61 | 0.21206 (11) | 0.23797 (13) | 0.24538 (5) | 0.0306 (3) | |
C62 | 0.16524 (12) | 0.15946 (15) | 0.18996 (6) | 0.0417 (4) | |
C63 | 0.05711 (14) | 0.20545 (18) | 0.14556 (7) | 0.0539 (5) | |
C64 | −0.00269 (14) | 0.33176 (17) | 0.15558 (7) | 0.0522 (5) | |
C65 | 0.04473 (13) | 0.41193 (16) | 0.21036 (7) | 0.0477 (4) | |
C66 | 0.15077 (13) | 0.36482 (14) | 0.25539 (6) | 0.0411 (4) | |
H1 | 0.43269 | 0.37417 | 0.24045 | 0.0572* | |
H2 | 0.56131 | 0.33633 | 0.39900 | 0.0326* | |
H3 | 0.54830 | 0.12422 | 0.45820 | 0.0336* | |
H5A | 0.22560 | 0.15468 | 0.36716 | 0.0386* | |
H5B | 0.22916 | 0.01382 | 0.32721 | 0.0386* | |
H6 | 0.37396 | 0.11376 | 0.27050 | 0.0345* | |
H13A | 0.62061 | −0.03829 | 0.38562 | 0.0427* | |
H13B | 0.57690 | 0.06996 | 0.32870 | 0.0427* | |
H22 | 0.36573 | 0.53916 | 0.38222 | 0.0489* | |
H23 | 0.24701 | 0.65933 | 0.44646 | 0.0592* | |
H24 | 0.20469 | 0.55407 | 0.53917 | 0.0593* | |
H25 | 0.28567 | 0.33070 | 0.56870 | 0.0605* | |
H26 | 0.40615 | 0.20936 | 0.50567 | 0.0469* | |
H32 | 0.73320 | 0.23031 | 0.30388 | 0.0625* | |
H33 | 0.93655 | 0.33313 | 0.32728 | 0.0777* | |
H34 | 1.07021 | 0.29772 | 0.42641 | 0.0718* | |
H35 | 1.00038 | 0.15992 | 0.50343 | 0.0646* | |
H36 | 0.79730 | 0.05679 | 0.48096 | 0.0501* | |
H62 | 0.20653 | 0.07507 | 0.18234 | 0.0500* | |
H63 | 0.02515 | 0.15064 | 0.10899 | 0.0647* | |
H64 | −0.07459 | 0.36310 | 0.12570 | 0.0627* | |
H65 | 0.00517 | 0.49808 | 0.21701 | 0.0573* | |
H66 | 0.18099 | 0.41853 | 0.29252 | 0.0494* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0586 (7) | 0.0752 (8) | 0.0630 (7) | −0.0297 (6) | 0.0070 (6) | 0.0227 (6) |
O4 | 0.0559 (6) | 0.0402 (5) | 0.0461 (5) | −0.0080 (4) | −0.0044 (5) | 0.0154 (4) |
N1 | 0.0267 (5) | 0.0356 (5) | 0.0253 (5) | −0.0036 (4) | 0.0056 (4) | 0.0048 (4) |
C1 | 0.0425 (8) | 0.0609 (9) | 0.0394 (7) | −0.0103 (7) | 0.0081 (6) | 0.0160 (7) |
C2 | 0.0221 (5) | 0.0320 (6) | 0.0264 (6) | 0.0005 (4) | 0.0024 (4) | 0.0001 (5) |
C3 | 0.0272 (6) | 0.0320 (6) | 0.0232 (5) | 0.0035 (5) | 0.0009 (4) | 0.0002 (5) |
C4 | 0.0343 (6) | 0.0322 (6) | 0.0277 (6) | 0.0008 (5) | 0.0054 (5) | 0.0013 (5) |
C5 | 0.0267 (6) | 0.0353 (6) | 0.0324 (6) | −0.0047 (5) | 0.0008 (5) | 0.0032 (5) |
C6 | 0.0264 (6) | 0.0345 (6) | 0.0244 (5) | 0.0021 (5) | 0.0025 (4) | −0.0001 (5) |
C13 | 0.0335 (6) | 0.0394 (7) | 0.0323 (6) | 0.0087 (5) | 0.0027 (5) | −0.0069 (5) |
C21 | 0.0227 (5) | 0.0329 (6) | 0.0295 (6) | 0.0000 (5) | 0.0010 (4) | −0.0052 (5) |
C22 | 0.0425 (7) | 0.0350 (7) | 0.0437 (8) | 0.0013 (6) | 0.0058 (6) | −0.0030 (6) |
C23 | 0.0405 (8) | 0.0370 (7) | 0.0665 (10) | 0.0092 (6) | 0.0013 (7) | −0.0161 (7) |
C24 | 0.0345 (7) | 0.0592 (9) | 0.0552 (9) | 0.0053 (6) | 0.0106 (7) | −0.0239 (8) |
C25 | 0.0470 (8) | 0.0666 (10) | 0.0411 (8) | 0.0051 (7) | 0.0170 (6) | −0.0077 (7) |
C26 | 0.0376 (7) | 0.0454 (8) | 0.0354 (7) | 0.0075 (6) | 0.0099 (5) | 0.0000 (6) |
C31 | 0.0289 (6) | 0.0395 (7) | 0.0369 (7) | 0.0102 (5) | 0.0088 (5) | −0.0056 (6) |
C32 | 0.0415 (8) | 0.0699 (10) | 0.0483 (8) | 0.0140 (7) | 0.0171 (7) | 0.0110 (8) |
C33 | 0.0499 (9) | 0.0666 (11) | 0.0873 (14) | 0.0055 (8) | 0.0365 (10) | 0.0123 (9) |
C34 | 0.0335 (8) | 0.0563 (9) | 0.0925 (14) | 0.0016 (7) | 0.0191 (8) | −0.0149 (9) |
C35 | 0.0341 (8) | 0.0657 (10) | 0.0584 (10) | 0.0081 (7) | 0.0016 (7) | −0.0175 (8) |
C36 | 0.0341 (7) | 0.0504 (8) | 0.0396 (7) | 0.0060 (6) | 0.0050 (5) | −0.0042 (6) |
C61 | 0.0273 (6) | 0.0414 (7) | 0.0230 (5) | 0.0037 (5) | 0.0048 (4) | 0.0048 (5) |
C62 | 0.0404 (7) | 0.0514 (8) | 0.0305 (7) | 0.0116 (6) | 0.0005 (5) | −0.0036 (6) |
C63 | 0.0469 (8) | 0.0779 (11) | 0.0310 (7) | 0.0146 (8) | −0.0066 (6) | −0.0097 (7) |
C64 | 0.0404 (8) | 0.0774 (10) | 0.0346 (7) | 0.0211 (7) | −0.0026 (6) | 0.0058 (7) |
C65 | 0.0398 (7) | 0.0539 (8) | 0.0469 (8) | 0.0176 (6) | 0.0025 (6) | 0.0031 (7) |
C66 | 0.0374 (7) | 0.0470 (8) | 0.0366 (7) | 0.0087 (6) | 0.0016 (5) | −0.0037 (6) |
O1—C1 | 1.2147 (18) | C62—C63 | 1.390 (2) |
O4—C4 | 1.2138 (16) | C63—C64 | 1.374 (2) |
N1—C1 | 1.3443 (18) | C64—C65 | 1.382 (2) |
N1—C2 | 1.4781 (15) | C65—C66 | 1.3847 (19) |
N1—C6 | 1.4829 (15) | C1—H1 | 0.9300 |
C2—C3 | 1.5288 (16) | C2—H2 | 0.9800 |
C2—C21 | 1.5301 (16) | C3—H3 | 0.9800 |
C3—C4 | 1.5096 (16) | C5—H5A | 0.9700 |
C3—C13 | 1.5479 (17) | C5—H5B | 0.9700 |
C4—C5 | 1.5072 (17) | C6—H6 | 0.9800 |
C5—C6 | 1.5271 (17) | C13—H13A | 0.9700 |
C6—C61 | 1.5178 (16) | C13—H13B | 0.9700 |
C13—C31 | 1.5037 (17) | C22—H22 | 0.9300 |
C21—C22 | 1.3897 (17) | C23—H23 | 0.9300 |
C21—C26 | 1.3870 (17) | C24—H24 | 0.9300 |
C22—C23 | 1.388 (2) | C25—H25 | 0.9300 |
C23—C24 | 1.376 (2) | C26—H26 | 0.9300 |
C24—C25 | 1.364 (2) | C32—H32 | 0.9300 |
C25—C26 | 1.390 (2) | C33—H33 | 0.9300 |
C31—C32 | 1.385 (2) | C34—H34 | 0.9300 |
C31—C36 | 1.3886 (19) | C35—H35 | 0.9300 |
C32—C33 | 1.389 (2) | C36—H36 | 0.9300 |
C33—C34 | 1.368 (3) | C62—H62 | 0.9300 |
C34—C35 | 1.371 (2) | C63—H63 | 0.9300 |
C35—C36 | 1.387 (2) | C64—H64 | 0.9300 |
C61—C62 | 1.3830 (17) | C65—H65 | 0.9300 |
C61—C66 | 1.3861 (18) | C66—H66 | 0.9300 |
O1···C6i | 3.2576 (16) | C66···H33iv | 2.9700 |
O4···C3ii | 3.4093 (15) | H1···C61 | 2.6700 |
O1···H22 | 2.8100 | H1···C66 | 3.0500 |
O1···H6i | 2.2900 | H1···C13i | 2.9600 |
O1···H13Bi | 2.9200 | H1···H13Bi | 2.3300 |
O1···H62i | 2.7500 | H2···O1 | 2.4100 |
O1···H2 | 2.4100 | H2···C31 | 2.7400 |
O4···H13A | 2.8500 | H2···C32 | 3.0500 |
O4···H3ii | 2.4400 | H2···C24v | 2.8100 |
O4···H26ii | 2.7300 | H3···C26 | 2.6700 |
N1···H13B | 2.6600 | H3···C36 | 2.9600 |
N1···H22 | 2.7200 | H3···H26 | 2.1100 |
N1···H66 | 2.7200 | H3···O4ii | 2.4400 |
C1···C22 | 3.459 (2) | H5A···C2 | 2.8800 |
C1···C66 | 3.239 (2) | H5A···C21 | 2.8300 |
C3···O4ii | 3.4093 (15) | H5A···C34iv | 3.0500 |
C4···C26 | 3.1751 (18) | H5A···C66 | 3.0500 |
C5···C21 | 3.2029 (17) | H5B···C64ix | 3.0100 |
C5···C26 | 3.5906 (18) | H5B···C65ix | 2.9900 |
C6···C13 | 3.3229 (17) | H5B···H64ix | 2.5000 |
C6···O1iii | 3.2576 (16) | H5B···H65ix | 2.4600 |
C13···C6 | 3.3229 (17) | H6···C3 | 3.0400 |
C21···C5 | 3.2029 (17) | H6···C13 | 3.0200 |
C22···C1 | 3.459 (2) | H6···H13B | 2.2800 |
C26···C4 | 3.1751 (18) | H6···H62 | 2.3200 |
C26···C5 | 3.5906 (18) | H6···O1iii | 2.2900 |
C66···C1 | 3.239 (2) | H13A···O4 | 2.8500 |
C1···H22 | 2.8700 | H13B···N1 | 2.6600 |
C1···H66 | 3.0400 | H13B···C6 | 2.7900 |
C1···H13Bi | 2.9200 | H13B···H6 | 2.2800 |
C2···H5A | 2.8800 | H13B···H32 | 2.3600 |
C3···H6 | 3.0400 | H13B···O1iii | 2.9200 |
C3···H26 | 2.5700 | H13B···C1iii | 2.9200 |
C4···H26 | 2.7400 | H13B···H1iii | 2.3300 |
C6···H13B | 2.7900 | H22···O1 | 2.8100 |
C13···H1iii | 2.9600 | H22···N1 | 2.7200 |
C13···H6 | 3.0200 | H22···C1 | 2.8700 |
C21···H5A | 2.8300 | H24···C33v | 3.1000 |
C22···H66 | 2.9900 | H24···C34v | 2.9800 |
C24···H34iv | 3.0800 | H24···C35v | 2.9900 |
C24···H2v | 2.8100 | H25···C62x | 3.0700 |
C25···H34iv | 3.0200 | H26···C3 | 2.5700 |
C26···H3 | 2.6700 | H26···C4 | 2.7400 |
C31···H2 | 2.7400 | H26···H3 | 2.1100 |
C32···H2 | 3.0500 | H26···O4ii | 2.7300 |
C33···H62i | 3.0900 | H32···H13B | 2.3600 |
C33···H24v | 3.1000 | H33···C65vi | 3.0000 |
C34···H5Avi | 3.0500 | H33···C66vi | 2.9700 |
C34···H24v | 2.9800 | H34···C24vi | 3.0800 |
C35···H24v | 2.9900 | H34···C25vi | 3.0200 |
C36···H3 | 2.9600 | H62···H6 | 2.3200 |
C61···H1 | 2.6700 | H62···O1iii | 2.7500 |
C62···H25vii | 3.0700 | H62···C33iii | 3.0900 |
C64···H5Bviii | 3.0100 | H64···H5Bviii | 2.5000 |
C65···H33iv | 3.0000 | H65···H5Bviii | 2.4600 |
C65···H5Bviii | 2.9900 | H66···N1 | 2.7200 |
C66···H1 | 3.0500 | H66···C1 | 3.0400 |
C66···H5A | 3.0500 | H66···C22 | 2.9900 |
C1—N1—C2 | 119.98 (10) | C2—C3—H3 | 108.00 |
C1—N1—C6 | 118.22 (10) | C4—C3—H3 | 108.00 |
C2—N1—C6 | 120.45 (9) | C13—C3—H3 | 108.00 |
O1—C1—N1 | 125.88 (13) | C4—C5—H5A | 109.00 |
N1—C2—C3 | 108.94 (9) | C4—C5—H5B | 109.00 |
N1—C2—C21 | 112.04 (9) | C6—C5—H5A | 109.00 |
C3—C2—C21 | 114.48 (9) | C6—C5—H5B | 109.00 |
C2—C3—C4 | 110.13 (9) | H5A—C5—H5B | 108.00 |
C2—C3—C13 | 113.31 (9) | N1—C6—H6 | 108.00 |
C4—C3—C13 | 108.63 (9) | C5—C6—H6 | 108.00 |
O4—C4—C3 | 122.70 (11) | C61—C6—H6 | 108.00 |
O4—C4—C5 | 121.22 (11) | C3—C13—H13A | 109.00 |
C3—C4—C5 | 116.07 (10) | C3—C13—H13B | 109.00 |
C4—C5—C6 | 113.46 (10) | C31—C13—H13A | 109.00 |
N1—C6—C5 | 109.26 (9) | C31—C13—H13B | 109.00 |
N1—C6—C61 | 113.10 (10) | H13A—C13—H13B | 108.00 |
C5—C6—C61 | 110.75 (10) | C21—C22—H22 | 120.00 |
C3—C13—C31 | 114.36 (10) | C23—C22—H22 | 120.00 |
C2—C21—C22 | 119.35 (11) | C22—C23—H23 | 120.00 |
C2—C21—C26 | 122.78 (10) | C24—C23—H23 | 120.00 |
C22—C21—C26 | 117.80 (11) | C23—C24—H24 | 120.00 |
C21—C22—C23 | 120.74 (13) | C25—C24—H24 | 120.00 |
C22—C23—C24 | 120.57 (13) | C24—C25—H25 | 120.00 |
C23—C24—C25 | 119.28 (14) | C26—C25—H25 | 120.00 |
C24—C25—C26 | 120.72 (14) | C21—C26—H26 | 120.00 |
C21—C26—C25 | 120.87 (12) | C25—C26—H26 | 120.00 |
C13—C31—C32 | 121.21 (12) | C31—C32—H32 | 120.00 |
C13—C31—C36 | 120.92 (11) | C33—C32—H32 | 120.00 |
C32—C31—C36 | 117.87 (12) | C32—C33—H33 | 120.00 |
C31—C32—C33 | 120.65 (15) | C34—C33—H33 | 120.00 |
C32—C33—C34 | 120.65 (17) | C33—C34—H34 | 120.00 |
C33—C34—C35 | 119.58 (16) | C35—C34—H34 | 120.00 |
C34—C35—C36 | 120.14 (15) | C34—C35—H35 | 120.00 |
C31—C36—C35 | 121.10 (13) | C36—C35—H35 | 120.00 |
C6—C61—C62 | 118.42 (11) | C31—C36—H36 | 119.00 |
C6—C61—C66 | 122.64 (10) | C35—C36—H36 | 119.00 |
C62—C61—C66 | 118.92 (11) | C61—C62—H62 | 120.00 |
C61—C62—C63 | 120.64 (13) | C63—C62—H62 | 120.00 |
C62—C63—C64 | 120.13 (14) | C62—C63—H63 | 120.00 |
C63—C64—C65 | 119.56 (14) | C64—C63—H63 | 120.00 |
C64—C65—C66 | 120.43 (13) | C63—C64—H64 | 120.00 |
C61—C66—C65 | 120.30 (12) | C65—C64—H64 | 120.00 |
O1—C1—H1 | 117.00 | C64—C65—H65 | 120.00 |
N1—C1—H1 | 117.00 | C66—C65—H65 | 120.00 |
N1—C2—H2 | 107.00 | C61—C66—H66 | 120.00 |
C3—C2—H2 | 107.00 | C65—C66—H66 | 120.00 |
C21—C2—H2 | 107.00 | ||
C2—N1—C1—O1 | −10.3 (2) | N1—C6—C61—C66 | −38.97 (15) |
C6—N1—C1—O1 | −177.08 (13) | C5—C6—C61—C62 | −94.24 (13) |
C1—N1—C2—C3 | −128.30 (11) | C5—C6—C61—C66 | 84.06 (14) |
C1—N1—C2—C21 | 104.00 (13) | C3—C13—C31—C32 | −109.37 (14) |
C6—N1—C2—C3 | 38.20 (13) | C3—C13—C31—C36 | 71.24 (15) |
C6—N1—C2—C21 | −89.50 (12) | C2—C21—C22—C23 | −178.23 (12) |
C1—N1—C6—C5 | −176.52 (11) | C26—C21—C22—C23 | −1.27 (19) |
C1—N1—C6—C61 | −52.68 (14) | C2—C21—C26—C25 | 178.42 (12) |
C2—N1—C6—C5 | 16.75 (14) | C22—C21—C26—C25 | 1.56 (19) |
C2—N1—C6—C61 | 140.59 (10) | C21—C22—C23—C24 | 0.0 (2) |
N1—C2—C3—C4 | −59.37 (12) | C22—C23—C24—C25 | 0.9 (2) |
N1—C2—C3—C13 | 62.53 (12) | C23—C24—C25—C26 | −0.6 (2) |
C21—C2—C3—C4 | 66.94 (12) | C24—C25—C26—C21 | −0.6 (2) |
C21—C2—C3—C13 | −171.17 (9) | C13—C31—C32—C33 | −179.22 (14) |
N1—C2—C21—C22 | −48.07 (14) | C36—C31—C32—C33 | 0.2 (2) |
N1—C2—C21—C26 | 135.12 (11) | C13—C31—C36—C35 | 179.15 (13) |
C3—C2—C21—C22 | −172.75 (11) | C32—C31—C36—C35 | −0.3 (2) |
C3—C2—C21—C26 | 10.44 (16) | C31—C32—C33—C34 | 0.1 (3) |
C2—C3—C4—O4 | −155.25 (11) | C32—C33—C34—C35 | −0.3 (3) |
C2—C3—C4—C5 | 25.61 (13) | C33—C34—C35—C36 | 0.2 (2) |
C13—C3—C4—O4 | 80.12 (14) | C34—C35—C36—C31 | 0.1 (2) |
C13—C3—C4—C5 | −99.03 (12) | C6—C61—C62—C63 | 177.20 (12) |
C2—C3—C13—C31 | 63.87 (13) | C66—C61—C62—C63 | −1.16 (19) |
C4—C3—C13—C31 | −173.40 (10) | C6—C61—C66—C65 | −178.53 (12) |
O4—C4—C5—C6 | −148.61 (12) | C62—C61—C66—C65 | −0.24 (19) |
C3—C4—C5—C6 | 30.55 (14) | C61—C62—C63—C64 | 1.6 (2) |
C4—C5—C6—N1 | −52.04 (13) | C62—C63—C64—C65 | −0.6 (2) |
C4—C5—C6—C61 | −177.26 (10) | C63—C64—C65—C66 | −0.8 (2) |
N1—C6—C61—C62 | 142.73 (11) | C64—C65—C66—C61 | 1.2 (2) |
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) −x+1, −y, −z+1; (iii) −x+1, y−1/2, −z+1/2; (iv) x−1, y, z; (v) −x+1, −y+1, −z+1; (vi) x+1, y, z; (vii) x, −y+1/2, z−1/2; (viii) −x, y+1/2, −z+1/2; (ix) −x, y−1/2, −z+1/2; (x) x, −y+1/2, z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C24—H24···Cgv | 0.93 | 2.81 | 3.651 (1) | 151 |
C34—H34···Cgvi | 0.93 | 2.97 | 3.890 (2) | 172 |
C2—H2···O1 | 0.98 | 2.41 | 2.8175 (15) | 105 |
C3—H3···O4ii | 0.98 | 2.44 | 3.4093 (15) | 170 |
C6—H6···O1iii | 0.98 | 2.29 | 3.2576 (16) | 168 |
Symmetry codes: (ii) −x+1, −y, −z+1; (iii) −x+1, y−1/2, −z+1/2; (v) −x+1, −y+1, −z+1; (vi) x+1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C25H23NO2 |
Mr | 369.44 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 200 |
a, b, c (Å) | 10.5355 (3), 9.3464 (2), 21.0493 (5) |
β (°) | 101.520 (3) |
V (Å3) | 2030.95 (9) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.41 × 0.37 × 0.29 |
Data collection | |
Diffractometer | Oxford Diffraction Gemini diffractometer |
Absorption correction | Multi-scan (CrysAlis RED; Oxford Diffraction, 2007) |
Tmin, Tmax | 0.969, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 29482, 6871, 3596 |
Rint | 0.041 |
(sin θ/λ)max (Å−1) | 0.756 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.048, 0.142, 1.00 |
No. of reflections | 6871 |
No. of parameters | 253 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.47, −0.21 |
Computer programs: CrysAlis CCD (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
C24—H24···Cgi | 0.93 | 2.81 | 3.651 (1) | 151 |
C34—H34···Cgii | 0.93 | 2.97 | 3.890 (2) | 172 |
C2—H2···O1 | 0.98 | 2.41 | 2.8175 (15) | 105 |
C3—H3···O4iii | 0.98 | 2.44 | 3.4093 (15) | 170 |
C6—H6···O1iv | 0.98 | 2.29 | 3.2576 (16) | 168 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+1, y, z; (iii) −x+1, −y, −z+1; (iv) −x+1, y−1/2, −z+1/2. |
Jayabharathi et al. (2007) have reported synthesis, stereochemistry and antimicrobial evaluation of t3-benzyl-r2,c6-diarylpiperidin- 4-one and its derivatives. Balamurugan et al. (2007) have reported a crystal structure of t3,t5-Dimethyl-r2,c-6-diphenylpiperidin-4-one wherein the piperidine ring is in chair form. The piperidine ring of the title molecule, C25H23NO2, is in distorted boat form. The phenyl ring at position 2 makes a dihedral angle of 80.6 (1)° with the phenyl ring of benzyl moiety at 3, and 61.2 (1)° with the phenyl ring at 6. The dihedral angle between the phenyl ring of the benzyl moiety and the phenyl ring at 6 is 84.2 (1)°. The formyl group at N, is nearly co-planar with the adjacent C2 and C6 atoms. The phenyl ring at 6 is in equatorial orientations. The phenyl ring at 2, the benzyl group at 3 have axial orientations. C—H···O and C—H···π intra- and inter- molecular hydrogen bonds are found in the crystal structure (see Fig. 2, and hydrogen bonding table).