Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806029990/fl2039sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806029990/fl2039Isup2.hkl |
CCDC reference: 624506
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.005 Å
- R factor = 0.055
- wR factor = 0.164
- Data-to-parameter ratio = 13.6
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 4.13 Ratio PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.10 Ratio
Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 48 Perc. PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C23 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C25 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5 PLAT360_ALERT_2_C Short C(sp3)-C(sp3) Bond C25 - C26 ... 1.42 Ang.
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 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
Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.
C26H25NO3 | F(000) = 848 |
Mr = 399.47 | Dx = 1.269 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 11.361 (2) Å | Cell parameters from 1603 reflections |
b = 10.304 (3) Å | θ = 2.6–22.3° |
c = 18.355 (4) Å | µ = 0.08 mm−1 |
β = 103.242 (3)° | T = 298 K |
V = 2091.5 (9) Å3 | Block, colorless |
Z = 4 | 0.42 × 0.38 × 0.21 mm |
Bruker SMART CCD area-detector diffractometer | 3688 independent reflections |
Radiation source: fine-focus sealed tube | 1767 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.054 |
φ and ω scans | θmax = 25.0°, θmin = 2.3° |
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997) | h = −13→13 |
Tmin = 0.966, Tmax = 0.983 | k = −11→12 |
10716 measured reflections | l = −21→15 |
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)] = 0.055 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.164 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0539P)2 + 0.9737P] where P = (Fo2 + 2Fc2)/3 |
3688 reflections | (Δ/σ)max < 0.001 |
271 parameters | Δρmax = 0.30 e Å−3 |
0 restraints | Δρmin = −0.23 e Å−3 |
Experimental. 1H NMR: (300 MHz, CDCl3): δ 7.95–7.82 (m, 4H), 7.41–7.14 (m, 6H), 7.07–7.01 (m, 2H), 5.12 (d, 1H), 4.67 (d, 1H), 3.36 (q, 2H), 3.20 (q, 2H), 1.23 (t, 3H), 1.08 (t, 3H). IR (KBr, pellet): 3268, 2977, 1633, 1592, 1475, 1372, 1296, 1218, 1145, 1096, 810, 748 cm-1. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.6192 (3) | 0.1803 (3) | 0.36282 (17) | 0.0624 (8) | |
O1 | 0.4943 (2) | 0.3032 (2) | 0.27688 (14) | 0.0648 (7) | |
O2 | 0.32515 (18) | 0.1255 (2) | 0.23816 (11) | 0.0486 (6) | |
O3 | 0.2741 (2) | 0.4257 (2) | 0.23628 (12) | 0.0553 (6) | |
H3 | 0.3238 | 0.3875 | 0.2180 | 0.083* | |
C1 | 0.5188 (3) | 0.1991 (3) | 0.30997 (19) | 0.0497 (9) | |
C2 | 0.4312 (3) | 0.0866 (3) | 0.29087 (18) | 0.0506 (9) | |
H2A | 0.4697 | 0.0159 | 0.2703 | 0.061* | |
H2B | 0.4097 | 0.0557 | 0.3360 | 0.061* | |
C3 | 0.3323 (3) | 0.1521 (3) | 0.16552 (18) | 0.0448 (8) | |
C4 | 0.4275 (3) | 0.1090 (3) | 0.1349 (2) | 0.0545 (9) | |
H4 | 0.4928 | 0.0654 | 0.1646 | 0.065* | |
C5 | 0.4237 (3) | 0.1316 (4) | 0.0616 (2) | 0.0625 (10) | |
H5 | 0.4868 | 0.1017 | 0.0416 | 0.075* | |
C6 | 0.3275 (3) | 0.1985 (3) | 0.01500 (19) | 0.0535 (10) | |
C7 | 0.3200 (4) | 0.2188 (4) | −0.0620 (2) | 0.0723 (12) | |
H7 | 0.3810 | 0.1870 | −0.0834 | 0.087* | |
C8 | 0.2263 (5) | 0.2834 (5) | −0.1053 (2) | 0.0825 (14) | |
H8 | 0.2222 | 0.2936 | −0.1561 | 0.099* | |
C9 | 0.1357 (4) | 0.3348 (4) | −0.0740 (2) | 0.0789 (13) | |
H9 | 0.0729 | 0.3818 | −0.1038 | 0.095* | |
C10 | 0.1384 (3) | 0.3170 (4) | 0.00036 (18) | 0.0586 (10) | |
H10 | 0.0771 | 0.3517 | 0.0203 | 0.070* | |
C11 | 0.2330 (3) | 0.2465 (3) | 0.04703 (18) | 0.0466 (9) | |
C12 | 0.2365 (3) | 0.2221 (3) | 0.12398 (16) | 0.0404 (8) | |
C13 | 0.1395 (3) | 0.2727 (3) | 0.15868 (16) | 0.0404 (8) | |
C14 | 0.0198 (3) | 0.2210 (3) | 0.13803 (16) | 0.0418 (8) | |
C15 | −0.0079 (3) | 0.1108 (3) | 0.09179 (17) | 0.0523 (9) | |
H15 | 0.0528 | 0.0711 | 0.0734 | 0.063* | |
C16 | −0.1221 (3) | 0.0617 (4) | 0.0737 (2) | 0.0634 (10) | |
H16 | −0.1382 | −0.0116 | 0.0434 | 0.076* | |
C17 | −0.2144 (4) | 0.1194 (4) | 0.0996 (2) | 0.0735 (12) | |
H17 | −0.2922 | 0.0851 | 0.0866 | 0.088* | |
C18 | −0.1921 (3) | 0.2252 (4) | 0.1439 (2) | 0.0680 (11) | |
H18 | −0.2549 | 0.2631 | 0.1610 | 0.082* | |
C19 | −0.0749 (3) | 0.2796 (3) | 0.16461 (19) | 0.0514 (9) | |
C20 | −0.0476 (3) | 0.3893 (4) | 0.2116 (2) | 0.0619 (10) | |
H20 | −0.1094 | 0.4316 | 0.2276 | 0.074* | |
C21 | 0.0670 (3) | 0.4337 (3) | 0.23369 (19) | 0.0567 (9) | |
H21 | 0.0834 | 0.5045 | 0.2658 | 0.068* | |
C22 | 0.1616 (3) | 0.3740 (3) | 0.20866 (17) | 0.0432 (8) | |
C23 | 0.6450 (3) | 0.0625 (4) | 0.4078 (2) | 0.0659 (11) | |
H23A | 0.7259 | 0.0329 | 0.4075 | 0.079* | |
H23B | 0.5887 | −0.0048 | 0.3853 | 0.079* | |
C24 | 0.6358 (5) | 0.0819 (5) | 0.4868 (2) | 0.1052 (16) | |
H24A | 0.6535 | 0.0017 | 0.5138 | 0.158* | |
H24B | 0.5554 | 0.1094 | 0.4876 | 0.158* | |
H24C | 0.6927 | 0.1470 | 0.5099 | 0.158* | |
C25 | 0.7079 (4) | 0.2855 (4) | 0.3814 (3) | 0.0853 (13) | |
H25A | 0.6749 | 0.3623 | 0.3535 | 0.102* | |
H25B | 0.7195 | 0.3055 | 0.4342 | 0.102* | |
C26 | 0.8224 (5) | 0.2585 (6) | 0.3663 (4) | 0.167 (3) | |
H26A | 0.8744 | 0.3324 | 0.3795 | 0.250* | |
H26B | 0.8126 | 0.2400 | 0.3139 | 0.250* | |
H26C | 0.8577 | 0.1847 | 0.3951 | 0.250* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0575 (19) | 0.0445 (18) | 0.076 (2) | 0.0042 (15) | −0.0042 (17) | 0.0002 (17) |
O1 | 0.0683 (16) | 0.0402 (15) | 0.0773 (18) | 0.0000 (13) | −0.0007 (13) | 0.0097 (13) |
O2 | 0.0509 (14) | 0.0528 (15) | 0.0408 (13) | 0.0043 (11) | 0.0080 (11) | 0.0031 (11) |
O3 | 0.0611 (15) | 0.0478 (14) | 0.0550 (15) | −0.0074 (12) | 0.0095 (12) | −0.0136 (12) |
C1 | 0.054 (2) | 0.039 (2) | 0.053 (2) | 0.0072 (17) | 0.0073 (18) | −0.0012 (18) |
C2 | 0.058 (2) | 0.042 (2) | 0.049 (2) | 0.0031 (17) | 0.0057 (17) | 0.0039 (17) |
C3 | 0.056 (2) | 0.040 (2) | 0.041 (2) | −0.0098 (17) | 0.0154 (17) | −0.0050 (16) |
C4 | 0.052 (2) | 0.053 (2) | 0.061 (2) | −0.0026 (18) | 0.0189 (18) | −0.0086 (19) |
C5 | 0.064 (3) | 0.064 (3) | 0.070 (3) | −0.014 (2) | 0.036 (2) | −0.018 (2) |
C6 | 0.067 (2) | 0.055 (2) | 0.045 (2) | −0.029 (2) | 0.026 (2) | −0.0147 (18) |
C7 | 0.095 (3) | 0.077 (3) | 0.053 (3) | −0.041 (3) | 0.036 (2) | −0.018 (2) |
C8 | 0.104 (4) | 0.106 (4) | 0.042 (2) | −0.059 (3) | 0.027 (3) | −0.009 (3) |
C9 | 0.083 (3) | 0.102 (4) | 0.046 (2) | −0.037 (3) | 0.004 (2) | 0.014 (2) |
C10 | 0.060 (2) | 0.073 (3) | 0.040 (2) | −0.024 (2) | 0.0075 (18) | 0.0045 (19) |
C11 | 0.052 (2) | 0.049 (2) | 0.0368 (19) | −0.0236 (17) | 0.0073 (17) | −0.0077 (16) |
C12 | 0.0465 (19) | 0.0408 (19) | 0.0352 (18) | −0.0118 (16) | 0.0122 (15) | −0.0063 (15) |
C13 | 0.049 (2) | 0.0371 (19) | 0.0335 (17) | −0.0033 (15) | 0.0064 (15) | 0.0042 (15) |
C14 | 0.046 (2) | 0.044 (2) | 0.0343 (18) | 0.0001 (16) | 0.0061 (15) | 0.0078 (16) |
C15 | 0.056 (2) | 0.054 (2) | 0.047 (2) | −0.0120 (18) | 0.0126 (17) | 0.0015 (18) |
C16 | 0.061 (3) | 0.065 (3) | 0.061 (2) | −0.019 (2) | 0.006 (2) | 0.001 (2) |
C17 | 0.051 (3) | 0.086 (3) | 0.076 (3) | −0.011 (2) | −0.002 (2) | 0.009 (3) |
C18 | 0.048 (2) | 0.081 (3) | 0.076 (3) | 0.009 (2) | 0.016 (2) | 0.024 (2) |
C19 | 0.052 (2) | 0.049 (2) | 0.052 (2) | 0.0030 (18) | 0.0099 (18) | 0.0133 (18) |
C20 | 0.057 (2) | 0.063 (3) | 0.067 (3) | 0.015 (2) | 0.0174 (19) | 0.008 (2) |
C21 | 0.071 (3) | 0.049 (2) | 0.050 (2) | 0.008 (2) | 0.0131 (19) | −0.0032 (17) |
C22 | 0.049 (2) | 0.040 (2) | 0.0380 (18) | −0.0002 (17) | 0.0035 (15) | 0.0025 (16) |
C23 | 0.065 (2) | 0.056 (3) | 0.068 (3) | 0.014 (2) | −0.002 (2) | 0.002 (2) |
C24 | 0.140 (4) | 0.099 (4) | 0.071 (3) | 0.036 (3) | 0.014 (3) | 0.000 (3) |
C25 | 0.064 (3) | 0.065 (3) | 0.112 (4) | −0.002 (2) | −0.011 (3) | −0.006 (3) |
C26 | 0.120 (5) | 0.167 (6) | 0.239 (8) | −0.060 (5) | 0.092 (5) | −0.072 (6) |
N1—C1 | 1.332 (4) | C13—C22 | 1.374 (4) |
N1—C23 | 1.459 (4) | C13—C14 | 1.429 (4) |
N1—C25 | 1.467 (5) | C14—C15 | 1.409 (4) |
O1—C1 | 1.232 (4) | C14—C19 | 1.414 (4) |
O2—C3 | 1.382 (3) | C15—C16 | 1.361 (4) |
O2—C2 | 1.419 (3) | C15—H15 | 0.9300 |
O3—C22 | 1.370 (3) | C16—C17 | 1.382 (5) |
O3—H3 | 0.8200 | C16—H16 | 0.9300 |
C1—C2 | 1.515 (4) | C17—C18 | 1.348 (5) |
C2—H2A | 0.9700 | C17—H17 | 0.9300 |
C2—H2B | 0.9700 | C18—C19 | 1.414 (5) |
C3—C12 | 1.380 (4) | C18—H18 | 0.9300 |
C3—C4 | 1.400 (4) | C19—C20 | 1.412 (5) |
C4—C5 | 1.356 (5) | C20—C21 | 1.352 (5) |
C4—H4 | 0.9300 | C20—H20 | 0.9300 |
C5—C6 | 1.404 (5) | C21—C22 | 1.403 (4) |
C5—H5 | 0.9300 | C21—H21 | 0.9300 |
C6—C7 | 1.412 (5) | C23—C24 | 1.490 (5) |
C6—C11 | 1.425 (5) | C23—H23A | 0.9700 |
C7—C8 | 1.348 (6) | C23—H23B | 0.9700 |
C7—H7 | 0.9300 | C24—H24A | 0.9600 |
C8—C9 | 1.393 (6) | C24—H24B | 0.9600 |
C8—H8 | 0.9300 | C24—H24C | 0.9600 |
C9—C10 | 1.370 (4) | C25—C26 | 1.418 (6) |
C9—H9 | 0.9300 | C25—H25A | 0.9700 |
C10—C11 | 1.412 (5) | C25—H25B | 0.9700 |
C10—H10 | 0.9300 | C26—H26A | 0.9600 |
C11—C12 | 1.426 (4) | C26—H26B | 0.9600 |
C12—C13 | 1.488 (4) | C26—H26C | 0.9600 |
C1—N1—C23 | 124.1 (3) | C19—C14—C13 | 120.1 (3) |
C1—N1—C25 | 119.4 (3) | C16—C15—C14 | 121.1 (3) |
C23—N1—C25 | 116.4 (3) | C16—C15—H15 | 119.5 |
C3—O2—C2 | 119.0 (2) | C14—C15—H15 | 119.5 |
C22—O3—H3 | 109.5 | C15—C16—C17 | 120.8 (4) |
O1—C1—N1 | 123.0 (3) | C15—C16—H16 | 119.6 |
O1—C1—C2 | 119.3 (3) | C17—C16—H16 | 119.6 |
N1—C1—C2 | 117.7 (3) | C18—C17—C16 | 120.1 (4) |
O2—C2—C1 | 110.6 (3) | C18—C17—H17 | 119.9 |
O2—C2—H2A | 109.5 | C16—C17—H17 | 119.9 |
C1—C2—H2A | 109.5 | C17—C18—C19 | 121.2 (4) |
O2—C2—H2B | 109.5 | C17—C18—H18 | 119.4 |
C1—C2—H2B | 109.5 | C19—C18—H18 | 119.4 |
H2A—C2—H2B | 108.1 | C20—C19—C18 | 122.9 (4) |
C12—C3—O2 | 115.1 (3) | C20—C19—C14 | 118.3 (3) |
C12—C3—C4 | 121.8 (3) | C18—C19—C14 | 118.8 (3) |
O2—C3—C4 | 123.1 (3) | C21—C20—C19 | 121.0 (3) |
C5—C4—C3 | 119.5 (3) | C21—C20—H20 | 119.5 |
C5—C4—H4 | 120.3 | C19—C20—H20 | 119.5 |
C3—C4—H4 | 120.3 | C20—C21—C22 | 120.7 (3) |
C4—C5—C6 | 122.1 (3) | C20—C21—H21 | 119.6 |
C4—C5—H5 | 118.9 | C22—C21—H21 | 119.6 |
C6—C5—H5 | 118.9 | O3—C22—C13 | 123.7 (3) |
C5—C6—C7 | 122.9 (4) | O3—C22—C21 | 115.3 (3) |
C5—C6—C11 | 118.3 (3) | C13—C22—C21 | 121.0 (3) |
C7—C6—C11 | 118.9 (4) | N1—C23—C24 | 113.0 (3) |
C8—C7—C6 | 121.4 (4) | N1—C23—H23A | 109.0 |
C8—C7—H7 | 119.3 | C24—C23—H23A | 109.0 |
C6—C7—H7 | 119.3 | N1—C23—H23B | 109.0 |
C7—C8—C9 | 120.2 (4) | C24—C23—H23B | 109.0 |
C7—C8—H8 | 119.9 | H23A—C23—H23B | 107.8 |
C9—C8—H8 | 119.9 | C23—C24—H24A | 109.5 |
C10—C9—C8 | 120.6 (4) | C23—C24—H24B | 109.5 |
C10—C9—H9 | 119.7 | H24A—C24—H24B | 109.5 |
C8—C9—H9 | 119.7 | C23—C24—H24C | 109.5 |
C9—C10—C11 | 120.9 (4) | H24A—C24—H24C | 109.5 |
C9—C10—H10 | 119.6 | H24B—C24—H24C | 109.5 |
C11—C10—H10 | 119.6 | C26—C25—N1 | 114.9 (4) |
C10—C11—C6 | 118.0 (3) | C26—C25—H25A | 108.5 |
C10—C11—C12 | 122.4 (3) | N1—C25—H25A | 108.5 |
C6—C11—C12 | 119.6 (3) | C26—C25—H25B | 108.5 |
C3—C12—C11 | 118.6 (3) | N1—C25—H25B | 108.5 |
C3—C12—C13 | 120.9 (3) | H25A—C25—H25B | 107.5 |
C11—C12—C13 | 120.4 (3) | C25—C26—H26A | 109.5 |
C22—C13—C14 | 118.5 (3) | C25—C26—H26B | 109.5 |
C22—C13—C12 | 120.8 (3) | H26A—C26—H26B | 109.5 |
C14—C13—C12 | 120.6 (3) | C25—C26—H26C | 109.5 |
C15—C14—C19 | 118.0 (3) | H26A—C26—H26C | 109.5 |
C15—C14—C13 | 121.9 (3) | H26B—C26—H26C | 109.5 |