Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270111015794/ku3044sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270111015794/ku3044Iasup2.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S0108270111015794/ku3044Iasup3.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S0108270111015794/ku3044IIasup5.cml | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270111015794/ku3044IIasup4.hkl |
CCDC references: 833416; 833417
For both compounds, data collection: COLLECT (Nonius, 1998); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1999); software used to prepare material for publication: WinGX (Farrugia, 1999) and publCIF (Westrip, 2010).
C24H23NO5 | F(000) = 856 |
Mr = 405.43 | Dx = 1.344 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 4631 reflections |
a = 7.6516 (1) Å | θ = 2.6–27.5° |
b = 14.7810 (3) Å | µ = 0.09 mm−1 |
c = 17.8063 (4) Å | T = 293 K |
β = 95.8175 (8)° | Prism, colourless |
V = 2003.49 (7) Å3 | 0.2 × 0.2 × 0.2 mm |
Z = 4 |
Nonius KappaCCD area-detector diffractometer | 4566 independent reflections |
Graphite monochromator | 3167 reflections with I > 2σ(I) |
Detector resolution: 0.055 pixels mm-1 | Rint = 0.033 |
φ and ω scans | θmax = 27.5°, θmin = 3.6° |
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997) | h = −9→9 |
Tmin = 0.981, Tmax = 0.981 | k = −18→19 |
8696 measured reflections | l = −23→23 |
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)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.126 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.059P)2 + 0.4255P] where P = (Fo2 + 2Fc2)/3 |
4566 reflections | (Δ/σ)max < 0.001 |
275 parameters | Δρmax = 0.18 e Å−3 |
0 restraints | Δρmin = −0.17 e Å−3 |
Experimental. 186 frames in 4 sets of φ scans + ω scans. Rotation/frame = 2 °. Crystal-detector distance = 35.0 mm. Measuring time = 50 s/°. |
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. |
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 > 2σ(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 | ||
N1 | 0.30792 (17) | 0.52864 (9) | 0.43674 (7) | 0.0380 (3) | |
H2 | 0.3184 | 0.4712 | 0.4607 | 0.057* | |
O1 | 0.25463 (18) | 0.40077 (8) | 0.53818 (7) | 0.0532 (3) | |
O2 | 0.12684 (17) | 0.44292 (8) | 0.63932 (7) | 0.0492 (3) | |
O3 | 0.3406 (2) | 0.61562 (8) | 0.33357 (7) | 0.0633 (4) | |
O4 | 0.10238 (16) | 1.00534 (8) | 0.35584 (6) | 0.0494 (3) | |
O5 | 0.25616 (17) | 1.11462 (7) | 0.45477 (7) | 0.0504 (3) | |
C1 | 0.1320 (2) | 0.61975 (11) | 0.60655 (8) | 0.0363 (4) | |
H1 | 0.0905 | 0.5975 | 0.6503 | 0.044* | |
C2 | 0.18995 (19) | 0.55772 (10) | 0.55571 (8) | 0.0327 (3) | |
C3 | 0.24941 (19) | 0.59109 (10) | 0.48853 (8) | 0.0332 (3) | |
C4 | 0.2505 (2) | 0.68393 (11) | 0.47678 (8) | 0.0361 (3) | |
H4 | 0.2895 | 0.7062 | 0.4326 | 0.043* | |
C5 | 0.19470 (19) | 0.74489 (10) | 0.52928 (8) | 0.0338 (3) | |
C6 | 0.1324 (2) | 0.71223 (11) | 0.59595 (8) | 0.0359 (3) | |
C7 | 0.1946 (2) | 0.45995 (11) | 0.57472 (9) | 0.0363 (4) | |
C8 | 0.1372 (3) | 0.35083 (13) | 0.66588 (12) | 0.0649 (6) | |
H8A | 0.0687 | 0.3126 | 0.6306 | 0.097* | |
H8B | 0.0923 | 0.3473 | 0.7142 | 0.097* | |
H8C | 0.2574 | 0.3313 | 0.6705 | 0.097* | |
C9 | 0.3473 (2) | 0.54225 (11) | 0.36497 (9) | 0.0382 (4) | |
C10 | 0.4012 (2) | 0.45859 (11) | 0.32554 (9) | 0.0367 (4) | |
C11 | 0.3653 (2) | 0.37167 (12) | 0.34866 (10) | 0.0483 (4) | |
H11 | 0.3055 | 0.3632 | 0.391 | 0.058* | |
C12 | 0.4176 (3) | 0.29714 (14) | 0.30929 (11) | 0.0596 (5) | |
H12 | 0.3924 | 0.2391 | 0.3252 | 0.071* | |
C13 | 0.5069 (2) | 0.30905 (15) | 0.24645 (11) | 0.0587 (5) | |
H13 | 0.5429 | 0.2591 | 0.2202 | 0.07* | |
C14 | 0.5425 (2) | 0.39501 (15) | 0.22288 (10) | 0.0551 (5) | |
H14 | 0.6027 | 0.403 | 0.1805 | 0.066* | |
C15 | 0.4898 (2) | 0.46981 (13) | 0.26151 (9) | 0.0455 (4) | |
H15 | 0.5135 | 0.5277 | 0.2447 | 0.055* | |
C16 | 0.2070 (2) | 0.84353 (10) | 0.51266 (8) | 0.0343 (3) | |
C17 | 0.1448 (2) | 0.87694 (10) | 0.44148 (8) | 0.0343 (3) | |
H17 | 0.0917 | 0.8375 | 0.4054 | 0.041* | |
C18 | 0.1608 (2) | 0.96744 (10) | 0.42373 (8) | 0.0355 (4) | |
C19 | 0.24404 (19) | 1.02684 (10) | 0.47741 (9) | 0.0368 (4) | |
C20 | 0.3070 (2) | 0.99382 (11) | 0.54698 (9) | 0.0408 (4) | |
H20 | 0.3632 | 1.0328 | 0.5827 | 0.049* | |
C21 | 0.2880 (2) | 0.90318 (11) | 0.56481 (9) | 0.0407 (4) | |
H21 | 0.3304 | 0.8824 | 0.6125 | 0.049* | |
C22 | −0.0106 (3) | 0.95324 (14) | 0.30494 (10) | 0.0559 (5) | |
H22A | 0.0525 | 0.9021 | 0.2882 | 0.084* | |
H22B | −0.0521 | 0.9897 | 0.2622 | 0.084* | |
H22C | −0.1087 | 0.9325 | 0.3298 | 0.084* | |
C23 | 0.3186 (3) | 1.17891 (12) | 0.51055 (12) | 0.0615 (5) | |
H23A | 0.4393 | 1.1663 | 0.5274 | 0.092* | |
H23B | 0.2496 | 1.1752 | 0.5526 | 0.092* | |
H23C | 0.3092 | 1.2386 | 0.4894 | 0.092* | |
C24 | 0.0653 (2) | 0.77239 (12) | 0.65522 (9) | 0.0469 (4) | |
H24A | −0.016 | 0.7392 | 0.6823 | 0.07* | |
H24B | 0.007 | 0.8239 | 0.6313 | 0.07* | |
H24C | 0.1621 | 0.7924 | 0.6897 | 0.07* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0548 (8) | 0.0281 (7) | 0.0324 (7) | 0.0019 (6) | 0.0110 (6) | 0.0006 (5) |
O1 | 0.0810 (9) | 0.0292 (6) | 0.0526 (7) | 0.0067 (6) | 0.0233 (6) | 0.0034 (5) |
O2 | 0.0737 (8) | 0.0322 (6) | 0.0443 (7) | 0.0007 (6) | 0.0195 (6) | 0.0097 (5) |
O3 | 0.1125 (12) | 0.0366 (7) | 0.0451 (7) | 0.0072 (7) | 0.0290 (7) | 0.0083 (6) |
O4 | 0.0683 (8) | 0.0389 (7) | 0.0395 (6) | −0.0006 (6) | −0.0012 (5) | 0.0074 (5) |
O5 | 0.0658 (8) | 0.0259 (6) | 0.0597 (8) | −0.0036 (6) | 0.0069 (6) | 0.0031 (5) |
C1 | 0.0443 (8) | 0.0353 (8) | 0.0301 (8) | 0.0029 (7) | 0.0074 (6) | 0.0049 (6) |
C2 | 0.0384 (8) | 0.0279 (8) | 0.0317 (8) | 0.0008 (6) | 0.0028 (6) | 0.0033 (6) |
C3 | 0.0399 (8) | 0.0292 (8) | 0.0308 (8) | 0.0017 (6) | 0.0046 (6) | −0.0011 (6) |
C4 | 0.0465 (9) | 0.0307 (8) | 0.0318 (8) | −0.0025 (7) | 0.0073 (6) | 0.0022 (6) |
C5 | 0.0391 (8) | 0.0286 (8) | 0.0335 (8) | 0.0008 (6) | 0.0024 (6) | 0.0002 (6) |
C6 | 0.0427 (8) | 0.0320 (8) | 0.0329 (8) | 0.0040 (7) | 0.0042 (6) | −0.0017 (6) |
C7 | 0.0413 (8) | 0.0322 (8) | 0.0354 (8) | −0.0005 (7) | 0.0033 (6) | 0.0033 (7) |
C8 | 0.0964 (15) | 0.0392 (11) | 0.0615 (12) | 0.0018 (11) | 0.0192 (11) | 0.0227 (9) |
C9 | 0.0477 (9) | 0.0339 (9) | 0.0336 (8) | −0.0023 (7) | 0.0076 (6) | 0.0015 (7) |
C10 | 0.0383 (8) | 0.0389 (9) | 0.0330 (8) | 0.0011 (7) | 0.0042 (6) | −0.0031 (7) |
C11 | 0.0621 (11) | 0.0393 (10) | 0.0453 (10) | 0.0011 (8) | 0.0150 (8) | −0.0061 (8) |
C12 | 0.0716 (13) | 0.0420 (11) | 0.0657 (13) | 0.0043 (9) | 0.0099 (10) | −0.0140 (9) |
C13 | 0.0540 (11) | 0.0652 (13) | 0.0566 (12) | 0.0148 (10) | 0.0043 (9) | −0.0251 (10) |
C14 | 0.0471 (10) | 0.0801 (15) | 0.0389 (9) | 0.0062 (10) | 0.0085 (7) | −0.0121 (10) |
C15 | 0.0465 (9) | 0.0549 (11) | 0.0358 (9) | −0.0001 (8) | 0.0074 (7) | −0.0011 (8) |
C16 | 0.0410 (8) | 0.0268 (8) | 0.0359 (8) | 0.0010 (6) | 0.0079 (6) | −0.0019 (6) |
C17 | 0.0409 (8) | 0.0295 (8) | 0.0329 (8) | −0.0001 (6) | 0.0057 (6) | −0.0036 (6) |
C18 | 0.0409 (8) | 0.0332 (9) | 0.0335 (8) | 0.0044 (7) | 0.0091 (6) | 0.0022 (6) |
C19 | 0.0404 (8) | 0.0259 (8) | 0.0455 (9) | 0.0010 (6) | 0.0116 (7) | −0.0012 (7) |
C20 | 0.0478 (9) | 0.0332 (9) | 0.0413 (9) | −0.0042 (7) | 0.0044 (7) | −0.0073 (7) |
C21 | 0.0526 (9) | 0.0340 (9) | 0.0349 (8) | 0.0005 (7) | 0.0012 (7) | 0.0008 (7) |
C22 | 0.0621 (11) | 0.0663 (13) | 0.0377 (10) | −0.0026 (10) | −0.0026 (8) | 0.0053 (9) |
C23 | 0.0808 (14) | 0.0286 (9) | 0.0778 (14) | −0.0111 (9) | 0.0211 (11) | −0.0116 (9) |
C24 | 0.0619 (11) | 0.0388 (9) | 0.0423 (9) | 0.0082 (8) | 0.0167 (8) | −0.0018 (8) |
N1—C9 | 1.3575 (19) | C11—C12 | 1.386 (2) |
N1—C3 | 1.4095 (19) | C11—H11 | 0.93 |
N1—H2 | 0.95 | C12—C13 | 1.381 (3) |
O1—C7 | 1.2082 (19) | C12—H12 | 0.93 |
O2—C7 | 1.3329 (18) | C13—C14 | 1.374 (3) |
O2—C8 | 1.441 (2) | C13—H13 | 0.93 |
O3—C9 | 1.2189 (19) | C14—C15 | 1.384 (3) |
O4—C18 | 1.3658 (18) | C14—H14 | 0.93 |
O4—C22 | 1.415 (2) | C15—H15 | 0.93 |
O5—C19 | 1.3647 (18) | C16—C21 | 1.381 (2) |
O5—C23 | 1.422 (2) | C16—C17 | 1.398 (2) |
C1—C6 | 1.380 (2) | C17—C18 | 1.383 (2) |
C1—C2 | 1.392 (2) | C17—H17 | 0.93 |
C1—H1 | 0.93 | C18—C19 | 1.403 (2) |
C2—C3 | 1.411 (2) | C19—C20 | 1.373 (2) |
C2—C7 | 1.484 (2) | C20—C21 | 1.388 (2) |
C3—C4 | 1.388 (2) | C20—H20 | 0.93 |
C4—C5 | 1.396 (2) | C21—H21 | 0.93 |
C4—H4 | 0.93 | C22—H22A | 0.96 |
C5—C6 | 1.409 (2) | C22—H22B | 0.96 |
C5—C16 | 1.493 (2) | C22—H22C | 0.96 |
C6—C24 | 1.509 (2) | C23—H23A | 0.96 |
C8—H8A | 0.96 | C23—H23B | 0.96 |
C8—H8B | 0.96 | C23—H23C | 0.96 |
C8—H8C | 0.96 | C24—H24A | 0.96 |
C9—C10 | 1.500 (2) | C24—H24B | 0.96 |
C10—C11 | 1.385 (2) | C24—H24C | 0.96 |
C10—C15 | 1.394 (2) | ||
C9—N1—C3 | 129.39 (13) | C14—C13—C12 | 119.69 (17) |
C9—N1—H2 | 122.6 | C14—C13—H13 | 120.2 |
C3—N1—H2 | 108 | C12—C13—H13 | 120.2 |
C7—O2—C8 | 116.65 (14) | C13—C14—C15 | 120.68 (17) |
C18—O4—C22 | 117.86 (13) | C13—C14—H14 | 119.7 |
C19—O5—C23 | 117.21 (14) | C15—C14—H14 | 119.7 |
C6—C1—C2 | 123.93 (14) | C14—C15—C10 | 120.13 (17) |
C6—C1—H1 | 118 | C14—C15—H15 | 119.9 |
C2—C1—H1 | 118 | C10—C15—H15 | 119.9 |
C1—C2—C3 | 118.18 (14) | C21—C16—C17 | 118.19 (14) |
C1—C2—C7 | 119.68 (13) | C21—C16—C5 | 121.56 (14) |
C3—C2—C7 | 122.09 (13) | C17—C16—C5 | 120.15 (14) |
C4—C3—N1 | 122.80 (13) | C18—C17—C16 | 121.27 (14) |
C4—C3—C2 | 118.72 (13) | C18—C17—H17 | 119.4 |
N1—C3—C2 | 118.48 (13) | C16—C17—H17 | 119.4 |
C3—C4—C5 | 122.03 (14) | O4—C18—C17 | 124.80 (14) |
C3—C4—H4 | 119 | O4—C18—C19 | 115.57 (14) |
C5—C4—H4 | 119 | C17—C18—C19 | 119.62 (14) |
C4—C5—C6 | 119.71 (14) | O5—C19—C20 | 125.20 (15) |
C4—C5—C16 | 117.91 (13) | O5—C19—C18 | 115.70 (14) |
C6—C5—C16 | 122.37 (13) | C20—C19—C18 | 119.09 (14) |
C1—C6—C5 | 117.41 (13) | C19—C20—C21 | 120.96 (15) |
C1—C6—C24 | 118.83 (14) | C19—C20—H20 | 119.5 |
C5—C6—C24 | 123.75 (14) | C21—C20—H20 | 119.5 |
O1—C7—O2 | 122.03 (14) | C16—C21—C20 | 120.84 (15) |
O1—C7—C2 | 125.74 (14) | C16—C21—H21 | 119.6 |
O2—C7—C2 | 112.22 (13) | C20—C21—H21 | 119.6 |
O2—C8—H8A | 109.5 | O4—C22—H22A | 109.5 |
O2—C8—H8B | 109.5 | O4—C22—H22B | 109.5 |
H8A—C8—H8B | 109.5 | H22A—C22—H22B | 109.5 |
O2—C8—H8C | 109.5 | O4—C22—H22C | 109.5 |
H8A—C8—H8C | 109.5 | H22A—C22—H22C | 109.5 |
H8B—C8—H8C | 109.5 | H22B—C22—H22C | 109.5 |
O3—C9—N1 | 124.08 (15) | O5—C23—H23A | 109.5 |
O3—C9—C10 | 121.31 (14) | O5—C23—H23B | 109.5 |
N1—C9—C10 | 114.60 (13) | H23A—C23—H23B | 109.5 |
C11—C10—C15 | 118.75 (15) | O5—C23—H23C | 109.5 |
C11—C10—C9 | 123.59 (14) | H23A—C23—H23C | 109.5 |
C15—C10—C9 | 117.65 (15) | H23B—C23—H23C | 109.5 |
C10—C11—C12 | 120.72 (17) | C6—C24—H24A | 109.5 |
C10—C11—H11 | 119.6 | C6—C24—H24B | 109.5 |
C12—C11—H11 | 119.6 | H24A—C24—H24B | 109.5 |
C13—C12—C11 | 120.03 (19) | C6—C24—H24C | 109.5 |
C13—C12—H12 | 120 | H24A—C24—H24C | 109.5 |
C11—C12—H12 | 120 | H24B—C24—H24C | 109.5 |
C6—C1—C2—C3 | −1.4 (2) | C15—C10—C11—C12 | 0.5 (3) |
C6—C1—C2—C7 | 176.10 (15) | C9—C10—C11—C12 | 179.48 (17) |
C9—N1—C3—C4 | −11.2 (3) | C10—C11—C12—C13 | 0.2 (3) |
C9—N1—C3—C2 | 169.84 (15) | C11—C12—C13—C14 | −0.5 (3) |
C1—C2—C3—C4 | 1.1 (2) | C12—C13—C14—C15 | 0.0 (3) |
C7—C2—C3—C4 | −176.27 (14) | C13—C14—C15—C10 | 0.7 (3) |
C1—C2—C3—N1 | −179.86 (14) | C11—C10—C15—C14 | −0.9 (2) |
C7—C2—C3—N1 | 2.7 (2) | C9—C10—C15—C14 | −179.98 (15) |
N1—C3—C4—C5 | −178.93 (14) | C4—C5—C16—C21 | −128.69 (16) |
C2—C3—C4—C5 | 0.0 (2) | C6—C5—C16—C21 | 50.1 (2) |
C3—C4—C5—C6 | −1.0 (2) | C4—C5—C16—C17 | 47.6 (2) |
C3—C4—C5—C16 | 177.82 (14) | C6—C5—C16—C17 | −133.54 (16) |
C2—C1—C6—C5 | 0.4 (2) | C21—C16—C17—C18 | −1.1 (2) |
C2—C1—C6—C24 | 179.74 (15) | C5—C16—C17—C18 | −177.51 (13) |
C4—C5—C6—C1 | 0.8 (2) | C22—O4—C18—C17 | 12.4 (2) |
C16—C5—C6—C1 | −177.97 (14) | C22—O4—C18—C19 | −168.40 (14) |
C4—C5—C6—C24 | −178.49 (15) | C16—C17—C18—O4 | −179.51 (14) |
C16—C5—C6—C24 | 2.7 (2) | C16—C17—C18—C19 | 1.3 (2) |
C8—O2—C7—O1 | 3.3 (2) | C23—O5—C19—C20 | −8.4 (2) |
C8—O2—C7—C2 | −175.43 (15) | C23—O5—C19—C18 | 171.96 (15) |
C1—C2—C7—O1 | −173.91 (16) | O4—C18—C19—O5 | −0.1 (2) |
C3—C2—C7—O1 | 3.5 (3) | C17—C18—C19—O5 | 179.12 (13) |
C1—C2—C7—O2 | 4.8 (2) | O4—C18—C19—C20 | −179.76 (14) |
C3—C2—C7—O2 | −177.84 (13) | C17—C18—C19—C20 | −0.5 (2) |
C3—N1—C9—O3 | 1.6 (3) | O5—C19—C20—C21 | 179.88 (14) |
C3—N1—C9—C10 | −178.31 (14) | C18—C19—C20—C21 | −0.5 (2) |
O3—C9—C10—C11 | −161.18 (18) | C17—C16—C21—C20 | 0.0 (2) |
N1—C9—C10—C11 | 18.7 (2) | C5—C16—C21—C20 | 176.40 (14) |
O3—C9—C10—C15 | 17.8 (2) | C19—C20—C21—C16 | 0.8 (2) |
N1—C9—C10—C15 | −162.28 (14) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H2···O1 | 0.95 | 1.83 | 2.6741 (17) | 146 |
C13—H13···O3i | 0.93 | 2.53 | 3.450 (2) | 172 |
C24—H24B···O5ii | 0.96 | 2.57 | 3.420 (2) | 148 |
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x, −y+2, −z+1. |
C24H21NO3 | Z = 2 |
Mr = 371.42 | F(000) = 392 |
Triclinic, P1 | Dx = 1.255 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.6722 (2) Å | Cell parameters from 3658 reflections |
b = 10.0140 (2) Å | θ = 2.6–27.5° |
c = 11.5677 (3) Å | µ = 0.08 mm−1 |
α = 71.422 (1)° | T = 293 K |
β = 84.479 (1)° | Prism, colourless |
γ = 67.753 (1)° | 0.2 × 0.2 × 0.08 mm |
V = 982.60 (4) Å3 |
Nonius KappaCCD area-detector diffractometer | 4442 independent reflections |
Graphite monochromator | 2768 reflections with I > 2σ(I) |
Detector resolution: 0.055 pixels mm-1 | Rint = 0.030 |
φ and ω scans | θmax = 27.5°, θmin = 3.7° |
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997) | h = −12→12 |
Tmin = 0.984, Tmax = 0.993 | k = −12→12 |
6912 measured reflections | l = −15→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)] = 0.062 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.155 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0427P)2 + 0.5035P] where P = (Fo2 + 2Fc2)/3 |
4442 reflections | (Δ/σ)max < 0.001 |
255 parameters | Δρmax = 0.21 e Å−3 |
0 restraints | Δρmin = −0.20 e Å−3 |
Experimental. 225 frames in 5 sets of φ scans + ω scans. Rotation/frame = 2 °. Crystal-detector distance = 35.0 mm. Measuring time = 160 s/°. |
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. |
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 > 2σ(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 | ||
N1 | 0.1805 (2) | 0.44050 (19) | 0.27717 (14) | 0.0437 (4) | |
H2 | 0.1891 | 0.3517 | 0.3033 | 0.066* | |
O1 | 0.52533 (19) | 0.2638 (2) | 0.64843 (15) | 0.0647 (5) | |
O2 | −0.18893 (19) | 0.85914 (17) | 0.54605 (14) | 0.0561 (4) | |
O3 | 0.2052 (3) | 0.6361 (2) | 0.12629 (15) | 0.0882 (7) | |
C1 | 0.2602 (2) | 0.5375 (2) | 0.54181 (18) | 0.0419 (5) | |
H1 | 0.3352 | 0.5045 | 0.6004 | 0.05* | |
C2 | 0.2821 (2) | 0.4592 (2) | 0.45615 (17) | 0.0390 (5) | |
C3 | 0.1669 (2) | 0.5118 (2) | 0.36943 (16) | 0.0381 (5) | |
C4 | 0.0387 (2) | 0.6350 (2) | 0.36939 (17) | 0.0400 (5) | |
H4 | −0.0361 | 0.6679 | 0.3107 | 0.048* | |
C5 | 0.0184 (2) | 0.7114 (2) | 0.45530 (17) | 0.0393 (5) | |
C6 | 0.1323 (3) | 0.6617 (2) | 0.54346 (18) | 0.0413 (5) | |
C7 | 0.4200 (3) | 0.3319 (2) | 0.4530 (2) | 0.0476 (5) | |
H7 | 0.435 | 0.307 | 0.3807 | 0.057* | |
C8 | 0.5269 (3) | 0.2465 (3) | 0.5383 (2) | 0.0511 (6) | |
H8 | 0.6081 | 0.1698 | 0.5203 | 0.061* | |
C9 | 0.6534 (3) | 0.1636 (4) | 0.7268 (3) | 0.0802 (9) | |
H9A | 0.7395 | 0.1357 | 0.6781 | 0.12* | |
H9B | 0.636 | 0.0742 | 0.7755 | 0.12* | |
H9C | 0.6704 | 0.2137 | 0.7791 | 0.12* | |
C10 | 0.2005 (3) | 0.5095 (2) | 0.15966 (18) | 0.0494 (6) | |
C11 | 0.2190 (3) | 0.4215 (3) | 0.07206 (19) | 0.0502 (6) | |
C12 | 0.2980 (4) | 0.4566 (3) | −0.0323 (2) | 0.0759 (9) | |
H12 | 0.3348 | 0.5337 | −0.0465 | 0.091* | |
C13 | 0.3223 (4) | 0.3770 (4) | −0.1154 (2) | 0.0919 (12) | |
H13 | 0.3769 | 0.3995 | −0.1847 | 0.11* | |
C14 | 0.2656 (4) | 0.2643 (4) | −0.0954 (3) | 0.0884 (11) | |
H14 | 0.2806 | 0.212 | −0.1519 | 0.106* | |
C15 | 0.1879 (4) | 0.2297 (4) | 0.0067 (3) | 0.0914 (11) | |
H15 | 0.1505 | 0.1531 | 0.0203 | 0.11* | |
C16 | 0.1641 (3) | 0.3086 (4) | 0.0908 (3) | 0.0715 (8) | |
H16 | 0.1105 | 0.2846 | 0.1604 | 0.086* | |
C17 | −0.1263 (3) | 0.8391 (2) | 0.45206 (19) | 0.0426 (5) | |
C18 | −0.1968 (3) | 0.9429 (2) | 0.33088 (19) | 0.0423 (5) | |
C19 | −0.1117 (3) | 0.9768 (2) | 0.2296 (2) | 0.0496 (6) | |
H19 | −0.0082 | 0.9296 | 0.2354 | 0.06* | |
C20 | −0.1800 (3) | 1.0802 (3) | 0.1206 (2) | 0.0626 (7) | |
H20 | −0.1224 | 1.1043 | 0.0538 | 0.075* | |
C21 | −0.3323 (4) | 1.1472 (3) | 0.1108 (2) | 0.0680 (8) | |
H21 | −0.3782 | 1.216 | 0.0372 | 0.082* | |
C22 | −0.4177 (3) | 1.1132 (3) | 0.2093 (3) | 0.0667 (8) | |
H22 | −0.5213 | 1.1576 | 0.2016 | 0.08* | |
C23 | −0.3506 (3) | 1.0132 (3) | 0.3202 (2) | 0.0540 (6) | |
H23 | −0.409 | 0.9933 | 0.3874 | 0.065* | |
C24 | 0.1249 (3) | 0.7417 (3) | 0.6361 (2) | 0.0563 (6) | |
H24A | 0.0759 | 0.7018 | 0.7073 | 0.084* | |
H24B | 0.0697 | 0.8483 | 0.6015 | 0.084* | |
H24C | 0.2243 | 0.7258 | 0.6583 | 0.084* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0621 (12) | 0.0352 (9) | 0.0329 (9) | −0.0151 (8) | 0.0001 (8) | −0.0125 (7) |
O1 | 0.0567 (11) | 0.0705 (11) | 0.0525 (10) | −0.0031 (9) | −0.0093 (8) | −0.0218 (8) |
O2 | 0.0651 (11) | 0.0500 (9) | 0.0444 (9) | −0.0101 (8) | 0.0085 (8) | −0.0184 (7) |
O3 | 0.168 (2) | 0.0583 (11) | 0.0455 (10) | −0.0539 (13) | 0.0230 (12) | −0.0166 (8) |
C1 | 0.0464 (13) | 0.0448 (11) | 0.0359 (10) | −0.0174 (10) | −0.0020 (9) | −0.0123 (9) |
C2 | 0.0449 (12) | 0.0373 (10) | 0.0343 (10) | −0.0153 (9) | 0.0047 (9) | −0.0110 (8) |
C3 | 0.0528 (13) | 0.0348 (10) | 0.0286 (9) | −0.0175 (9) | 0.0043 (9) | −0.0114 (8) |
C4 | 0.0500 (13) | 0.0369 (10) | 0.0307 (10) | −0.0139 (9) | −0.0034 (9) | −0.0084 (8) |
C5 | 0.0495 (13) | 0.0330 (10) | 0.0344 (10) | −0.0147 (9) | 0.0032 (9) | −0.0102 (8) |
C6 | 0.0523 (13) | 0.0412 (11) | 0.0348 (10) | −0.0205 (10) | 0.0038 (9) | −0.0141 (8) |
C7 | 0.0478 (14) | 0.0511 (12) | 0.0450 (12) | −0.0146 (11) | 0.0048 (10) | −0.0213 (10) |
C8 | 0.0473 (14) | 0.0513 (13) | 0.0538 (13) | −0.0143 (11) | 0.0047 (11) | −0.0204 (11) |
C9 | 0.0668 (19) | 0.082 (2) | 0.0715 (18) | −0.0057 (15) | −0.0229 (15) | −0.0156 (15) |
C10 | 0.0669 (16) | 0.0427 (12) | 0.0333 (11) | −0.0147 (11) | 0.0003 (10) | −0.0110 (9) |
C11 | 0.0567 (15) | 0.0495 (13) | 0.0333 (11) | −0.0027 (11) | −0.0078 (10) | −0.0160 (9) |
C12 | 0.114 (3) | 0.0601 (16) | 0.0395 (13) | −0.0190 (16) | 0.0076 (14) | −0.0150 (12) |
C13 | 0.131 (3) | 0.079 (2) | 0.0379 (14) | −0.005 (2) | 0.0078 (16) | −0.0230 (14) |
C14 | 0.104 (3) | 0.093 (2) | 0.0647 (19) | −0.005 (2) | −0.0143 (18) | −0.0533 (18) |
C15 | 0.091 (2) | 0.116 (3) | 0.102 (3) | −0.041 (2) | 0.010 (2) | −0.079 (2) |
C16 | 0.0711 (19) | 0.095 (2) | 0.0719 (17) | −0.0356 (16) | 0.0126 (14) | −0.0532 (16) |
C17 | 0.0534 (14) | 0.0340 (10) | 0.0419 (11) | −0.0162 (10) | 0.0037 (10) | −0.0141 (9) |
C18 | 0.0486 (13) | 0.0322 (10) | 0.0454 (12) | −0.0121 (9) | −0.0001 (10) | −0.0140 (9) |
C19 | 0.0541 (14) | 0.0416 (12) | 0.0472 (12) | −0.0134 (10) | 0.0001 (11) | −0.0107 (10) |
C20 | 0.079 (2) | 0.0510 (14) | 0.0473 (13) | −0.0202 (14) | −0.0005 (13) | −0.0055 (11) |
C21 | 0.082 (2) | 0.0493 (14) | 0.0567 (16) | −0.0108 (14) | −0.0182 (15) | −0.0058 (12) |
C22 | 0.0527 (16) | 0.0540 (15) | 0.0797 (19) | −0.0033 (12) | −0.0168 (14) | −0.0172 (14) |
C23 | 0.0518 (15) | 0.0452 (12) | 0.0634 (15) | −0.0139 (11) | 0.0040 (12) | −0.0201 (11) |
C24 | 0.0592 (16) | 0.0669 (15) | 0.0547 (14) | −0.0222 (13) | 0.0043 (11) | −0.0362 (12) |
N1—C10 | 1.347 (3) | C11—C12 | 1.386 (4) |
N1—C3 | 1.433 (2) | C12—C13 | 1.385 (4) |
N1—H2 | 0.8167 | C12—H12 | 0.93 |
O1—C8 | 1.337 (3) | C13—C14 | 1.381 (5) |
O1—C9 | 1.435 (3) | C13—H13 | 0.93 |
O2—C17 | 1.228 (2) | C14—C15 | 1.359 (5) |
O3—C10 | 1.219 (3) | C14—H14 | 0.93 |
C1—C6 | 1.387 (3) | C15—C16 | 1.390 (4) |
C1—C2 | 1.404 (3) | C15—H15 | 0.93 |
C1—H1 | 0.93 | C16—H16 | 0.93 |
C2—C3 | 1.400 (3) | C17—C18 | 1.493 (3) |
C2—C7 | 1.462 (3) | C18—C23 | 1.382 (3) |
C3—C4 | 1.379 (3) | C18—C19 | 1.392 (3) |
C4—C5 | 1.394 (3) | C19—C20 | 1.382 (3) |
C4—H4 | 0.93 | C19—H19 | 0.93 |
C5—C6 | 1.407 (3) | C20—C21 | 1.367 (4) |
C5—C17 | 1.490 (3) | C20—H20 | 0.93 |
C6—C24 | 1.511 (3) | C21—C22 | 1.371 (4) |
C7—C8 | 1.327 (3) | C21—H21 | 0.93 |
C7—H7 | 0.93 | C22—C23 | 1.385 (3) |
C8—H8 | 0.93 | C22—H22 | 0.93 |
C9—H9A | 0.96 | C23—H23 | 0.93 |
C9—H9B | 0.96 | C24—H24A | 0.96 |
C9—H9C | 0.96 | C24—H24B | 0.96 |
C10—C11 | 1.500 (3) | C24—H24C | 0.96 |
C11—C16 | 1.373 (4) | ||
C10—N1—C3 | 121.26 (17) | C13—C12—H12 | 120 |
C10—N1—H2 | 123.4 | C11—C12—H12 | 120 |
C3—N1—H2 | 114.5 | C14—C13—C12 | 120.0 (3) |
C8—O1—C9 | 116.0 (2) | C14—C13—H13 | 120 |
C6—C1—C2 | 123.29 (19) | C12—C13—H13 | 120 |
C6—C1—H1 | 118.4 | C15—C14—C13 | 120.1 (3) |
C2—C1—H1 | 118.4 | C15—C14—H14 | 120 |
C3—C2—C1 | 116.84 (18) | C13—C14—H14 | 120 |
C3—C2—C7 | 120.59 (18) | C14—C15—C16 | 120.1 (3) |
C1—C2—C7 | 122.53 (19) | C14—C15—H15 | 120 |
C4—C3—C2 | 120.89 (17) | C16—C15—H15 | 120 |
C4—C3—N1 | 118.35 (18) | C11—C16—C15 | 120.6 (3) |
C2—C3—N1 | 120.75 (18) | C11—C16—H16 | 119.7 |
C3—C4—C5 | 121.58 (18) | C15—C16—H16 | 119.7 |
C3—C4—H4 | 119.2 | O2—C17—C5 | 121.63 (19) |
C5—C4—H4 | 119.2 | O2—C17—C18 | 119.83 (19) |
C4—C5—C6 | 118.98 (19) | C5—C17—C18 | 118.53 (18) |
C4—C5—C17 | 118.09 (18) | C23—C18—C19 | 118.9 (2) |
C6—C5—C17 | 122.89 (17) | C23—C18—C17 | 119.2 (2) |
C1—C6—C5 | 118.42 (18) | C19—C18—C17 | 121.9 (2) |
C1—C6—C24 | 118.45 (19) | C20—C19—C18 | 120.5 (2) |
C5—C6—C24 | 123.07 (19) | C20—C19—H19 | 119.8 |
C8—C7—C2 | 129.5 (2) | C18—C19—H19 | 119.8 |
C8—C7—H7 | 115.3 | C21—C20—C19 | 120.0 (3) |
C2—C7—H7 | 115.3 | C21—C20—H20 | 120 |
C7—C8—O1 | 124.2 (2) | C19—C20—H20 | 120 |
C7—C8—H8 | 117.9 | C20—C21—C22 | 120.2 (2) |
O1—C8—H8 | 117.9 | C20—C21—H21 | 119.9 |
O1—C9—H9A | 109.5 | C22—C21—H21 | 119.9 |
O1—C9—H9B | 109.5 | C21—C22—C23 | 120.4 (3) |
H9A—C9—H9B | 109.5 | C21—C22—H22 | 119.8 |
O1—C9—H9C | 109.5 | C23—C22—H22 | 119.8 |
H9A—C9—H9C | 109.5 | C18—C23—C22 | 120.0 (2) |
H9B—C9—H9C | 109.5 | C18—C23—H23 | 120 |
O3—C10—N1 | 121.88 (19) | C22—C23—H23 | 120 |
O3—C10—C11 | 121.6 (2) | C6—C24—H24A | 109.5 |
N1—C10—C11 | 116.48 (19) | C6—C24—H24B | 109.5 |
C16—C11—C12 | 119.1 (2) | H24A—C24—H24B | 109.5 |
C16—C11—C10 | 123.7 (2) | C6—C24—H24C | 109.5 |
C12—C11—C10 | 117.2 (2) | H24A—C24—H24C | 109.5 |
C13—C12—C11 | 120.1 (3) | H24B—C24—H24C | 109.5 |
C6—C1—C2—C3 | −0.1 (3) | O3—C10—C11—C12 | 25.1 (4) |
C6—C1—C2—C7 | 177.7 (2) | N1—C10—C11—C12 | −154.1 (2) |
C1—C2—C3—C4 | 0.0 (3) | C16—C11—C12—C13 | −0.8 (4) |
C7—C2—C3—C4 | −177.9 (2) | C10—C11—C12—C13 | 178.4 (2) |
C1—C2—C3—N1 | 178.95 (19) | C11—C12—C13—C14 | 1.1 (5) |
C7—C2—C3—N1 | 1.1 (3) | C12—C13—C14—C15 | −1.0 (5) |
C10—N1—C3—C4 | 70.6 (3) | C13—C14—C15—C16 | 0.6 (5) |
C10—N1—C3—C2 | −108.4 (2) | C12—C11—C16—C15 | 0.3 (4) |
C2—C3—C4—C5 | −0.2 (3) | C10—C11—C16—C15 | −178.8 (3) |
N1—C3—C4—C5 | −179.14 (19) | C14—C15—C16—C11 | −0.2 (5) |
C3—C4—C5—C6 | 0.4 (3) | C4—C5—C17—O2 | 140.2 (2) |
C3—C4—C5—C17 | −177.39 (19) | C6—C5—C17—O2 | −37.5 (3) |
C2—C1—C6—C5 | 0.3 (3) | C4—C5—C17—C18 | −38.7 (3) |
C2—C1—C6—C24 | −176.9 (2) | C6—C5—C17—C18 | 143.6 (2) |
C4—C5—C6—C1 | −0.5 (3) | O2—C17—C18—C23 | −28.3 (3) |
C17—C5—C6—C1 | 177.2 (2) | C5—C17—C18—C23 | 150.6 (2) |
C4—C5—C6—C24 | 176.6 (2) | O2—C17—C18—C19 | 148.4 (2) |
C17—C5—C6—C24 | −5.7 (3) | C5—C17—C18—C19 | −32.6 (3) |
C3—C2—C7—C8 | −164.7 (2) | C23—C18—C19—C20 | 0.6 (3) |
C1—C2—C7—C8 | 17.6 (4) | C17—C18—C19—C20 | −176.1 (2) |
C2—C7—C8—O1 | 0.4 (4) | C18—C19—C20—C21 | −1.6 (4) |
C9—O1—C8—C7 | −178.1 (3) | C19—C20—C21—C22 | 0.6 (4) |
C3—N1—C10—O3 | −1.4 (4) | C20—C21—C22—C23 | 1.3 (4) |
C3—N1—C10—C11 | 177.8 (2) | C19—C18—C23—C22 | 1.3 (3) |
O3—C10—C11—C16 | −155.8 (3) | C17—C18—C23—C22 | 178.1 (2) |
N1—C10—C11—C16 | 25.0 (3) | C21—C22—C23—C18 | −2.2 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H2···O2i | 0.82 | 2.27 | 3.021 (2) | 153 |
C14—H14···Cg3ii | 0.93 | 2.99 | 3.820 (4) | 150 |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x, −y+1, −z. |