Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680602157X/er2009sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680602157X/er2009Isup2.hkl |
CCDC reference: 613673
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.003 Å
- R factor = 0.042
- wR factor = 0.110
- Data-to-parameter ratio = 12.7
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT230_ALERT_2_C Hirshfeld Test Diff for C2 - C3 .. 5.85 su PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N PLAT480_ALERT_4_C Long H...A H-Bond Reported H1 .. O9 .. 2.64 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CAD-4-PC Software (Enraf-Nonius, 1993); cell refinement: CAD-4-PC Software; data reduction: DATRD2 in NRCVAX (Gabe et al., 1989); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: WinGX (Farrugia, 1999).
C32H24N2O6 | F(000) = 556 |
Mr = 532.53 | Dx = 1.364 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 25 reflections |
a = 11.316 (1) Å | θ = 20.0–25.0° |
b = 8.330 (1) Å | µ = 0.10 mm−1 |
c = 13.880 (2) Å | T = 295 K |
β = 97.728 (9)° | Cube, pale yellow |
V = 1296.6 (2) Å3 | 0.34 × 0.34 × 0.34 mm |
Z = 2 |
Enraf-Nonius CAD-4 diffractometer | Rint = 0.000 |
Radiation source: fine-focus sealed tube | θmax = 25.0°, θmin = 2.9° |
Graphite monochromator | h = −13→13 |
ω scans | k = 0→9 |
2296 measured reflections | l = 0→16 |
2296 independent reflections | 3 standard reflections every 120 min |
1638 reflections with I > 2σ(I) | intensity decay: 0.5% |
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)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.110 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0433P)2 + 0.4238P] where P = (Fo2 + 2Fc2)/3 |
2296 reflections | (Δ/σ)max = 0.006 |
181 parameters | Δρmax = 0.19 e Å−3 |
0 restraints | Δρmin = −0.14 e Å−3 |
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. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) 4.2358 (0.0054) x + 3.5480 (0.0020) y + 10.6307 (0.0046) z = 8.5853 (0.0018) * -0.0026 (0.0018) C1 * 0.0218 (0.0021) C2 * 0.0548 (0.0021) C3 * 0.0372 (0.0019) C4 * -0.0139 (0.0017) C4A * -0.0132 (0.0017) C9 * -0.0190 (0.0017) C9A * 0.0241 (0.0018) C5 * 0.0682 (0.0020) C6 * 0.0367 (0.0020) C7 * -0.0152 (0.0018) C8 * -0.0351 (0.0017) C8A * -0.1146 (0.0016) C10 * -0.0291 (0.0017) C10A Rms deviation of fitted atoms = 0.0444 |
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 | 0.06637 (16) | 0.2101 (2) | 0.80619 (12) | 0.0858 (6) | |
O2 | 0.24334 (15) | 0.2982 (2) | 0.82085 (12) | 0.0854 (6) | |
O9 | 0.48438 (13) | 0.2286 (2) | 0.54283 (13) | 0.0796 (5) | |
N | 0.15881 (15) | 0.2324 (2) | 0.77504 (12) | 0.0497 (4) | |
C1 | 0.4565 (2) | −0.0539 (3) | 0.64346 (17) | 0.0651 (7) | |
H1 | 0.524 | −0.0432 | 0.6125 | 0.078* | |
C2 | 0.4420 (2) | −0.1881 (3) | 0.69632 (18) | 0.0765 (8) | |
H2 | 0.4988 | −0.2693 | 0.7003 | 0.092* | |
C3 | 0.3432 (2) | −0.2045 (3) | 0.74425 (18) | 0.0772 (7) | |
H3 | 0.3345 | −0.2957 | 0.7814 | 0.093* | |
C4 | 0.2574 (2) | −0.0851 (3) | 0.73693 (16) | 0.0625 (6) | |
H4 | 0.191 | −0.0962 | 0.7692 | 0.075* | |
C4A | 0.27012 (16) | 0.0511 (2) | 0.68162 (13) | 0.0453 (5) | |
C5 | 0.12032 (18) | 0.4543 (2) | 0.61030 (15) | 0.0527 (5) | |
H5 | 0.0521 | 0.4466 | 0.6406 | 0.063* | |
C6 | 0.1405 (2) | 0.5918 (3) | 0.56053 (17) | 0.0638 (6) | |
H6 | 0.0869 | 0.6767 | 0.5584 | 0.077* | |
C7 | 0.2398 (2) | 0.6041 (3) | 0.51388 (18) | 0.0680 (6) | |
H7 | 0.2528 | 0.6965 | 0.4792 | 0.082* | |
C8 | 0.3192 (2) | 0.4805 (3) | 0.51862 (16) | 0.0606 (6) | |
H8 | 0.3862 | 0.4892 | 0.4869 | 0.073* | |
C8A | 0.30146 (16) | 0.3405 (2) | 0.57054 (13) | 0.0462 (5) | |
C9 | 0.39230 (17) | 0.2126 (3) | 0.57908 (14) | 0.0533 (5) | |
C9A | 0.37151 (16) | 0.0677 (3) | 0.63519 (14) | 0.0491 (5) | |
C10 | 0.17176 (15) | 0.1757 (2) | 0.66974 (12) | 0.0396 (4) | |
C10A | 0.19957 (15) | 0.3267 (2) | 0.61629 (13) | 0.0410 (4) | |
C11 | 0.05311 (15) | 0.1013 (2) | 0.62416 (13) | 0.0400 (4) | |
H11A | 0.0326 | 0.0137 | 0.6649 | 0.048* | |
H11B | −0.0093 | 0.1815 | 0.6219 | 0.048* | |
C12 | 0.05872 (15) | 0.0383 (2) | 0.52187 (13) | 0.0390 (4) | |
H12A | 0.0775 | 0.1263 | 0.4807 | 0.047* | |
H12B | 0.1221 | −0.0404 | 0.5239 | 0.047* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0850 (11) | 0.1129 (15) | 0.0679 (11) | −0.0351 (11) | 0.0415 (9) | −0.0332 (10) |
O2 | 0.0731 (10) | 0.1266 (16) | 0.0552 (10) | −0.0290 (11) | 0.0034 (8) | −0.0340 (10) |
O9 | 0.0569 (9) | 0.0998 (14) | 0.0895 (12) | −0.0023 (9) | 0.0371 (9) | −0.0094 (10) |
N | 0.0560 (10) | 0.0528 (10) | 0.0418 (9) | −0.0053 (9) | 0.0121 (8) | −0.0062 (8) |
C1 | 0.0556 (13) | 0.0794 (18) | 0.0580 (14) | 0.0161 (12) | −0.0012 (11) | −0.0133 (13) |
C2 | 0.0743 (16) | 0.0843 (19) | 0.0658 (16) | 0.0334 (15) | −0.0084 (13) | −0.0078 (14) |
C3 | 0.0932 (19) | 0.0674 (16) | 0.0646 (16) | 0.0196 (15) | −0.0131 (14) | 0.0141 (13) |
C4 | 0.0671 (14) | 0.0652 (15) | 0.0534 (13) | 0.0090 (12) | 0.0014 (11) | 0.0092 (11) |
C4A | 0.0460 (11) | 0.0504 (12) | 0.0368 (10) | 0.0022 (9) | −0.0044 (8) | −0.0042 (9) |
C5 | 0.0514 (11) | 0.0470 (12) | 0.0613 (13) | −0.0030 (10) | 0.0131 (10) | 0.0013 (10) |
C6 | 0.0679 (14) | 0.0457 (12) | 0.0784 (16) | −0.0021 (11) | 0.0115 (12) | 0.0056 (12) |
C7 | 0.0811 (16) | 0.0517 (14) | 0.0713 (15) | −0.0133 (13) | 0.0106 (13) | 0.0093 (12) |
C8 | 0.0592 (13) | 0.0677 (15) | 0.0576 (13) | −0.0211 (12) | 0.0176 (11) | −0.0002 (11) |
C8A | 0.0433 (10) | 0.0541 (12) | 0.0413 (10) | −0.0094 (9) | 0.0065 (8) | −0.0076 (9) |
C9 | 0.0456 (11) | 0.0684 (15) | 0.0472 (11) | −0.0070 (10) | 0.0102 (9) | −0.0149 (10) |
C9A | 0.0414 (10) | 0.0602 (13) | 0.0437 (11) | 0.0062 (10) | −0.0016 (9) | −0.0145 (10) |
C10 | 0.0389 (9) | 0.0444 (11) | 0.0357 (9) | −0.0028 (8) | 0.0061 (8) | −0.0051 (8) |
C10A | 0.0400 (9) | 0.0423 (11) | 0.0404 (10) | −0.0080 (8) | 0.0041 (8) | −0.0054 (8) |
C11 | 0.0391 (9) | 0.0381 (10) | 0.0431 (10) | −0.0036 (8) | 0.0072 (8) | 0.0017 (8) |
C12 | 0.0392 (9) | 0.0362 (10) | 0.0412 (10) | −0.0017 (8) | 0.0037 (7) | 0.0012 (8) |
O1—N | 1.199 (2) | C6—C7 | 1.375 (3) |
O2—N | 1.207 (2) | C6—H6 | 0.93 |
O9—C9 | 1.224 (2) | C7—C8 | 1.362 (3) |
N—C10 | 1.562 (2) | C7—H7 | 0.93 |
C1—C2 | 1.359 (4) | C8—C8A | 1.400 (3) |
C1—C9A | 1.390 (3) | C8—H8 | 0.93 |
C1—H1 | 0.93 | C8A—C10A | 1.394 (2) |
C2—C3 | 1.382 (4) | C8A—C9 | 1.474 (3) |
C2—H2 | 0.93 | C9—C9A | 1.473 (3) |
C3—C4 | 1.384 (3) | C10—C10A | 1.515 (3) |
C3—H3 | 0.93 | C10—C11 | 1.536 (2) |
C4—C4A | 1.388 (3) | C11—C12 | 1.523 (2) |
C4—H4 | 0.93 | C11—H11A | 0.97 |
C4A—C9A | 1.396 (3) | C11—H11B | 0.97 |
C4A—C10 | 1.515 (3) | C12—C12i | 1.525 (3) |
C5—C10A | 1.386 (3) | C12—H12A | 0.97 |
C5—C6 | 1.372 (3) | C12—H12B | 0.97 |
C5—H5 | 0.93 | ||
O1—N—O2 | 123.27 (17) | C10A—C8A—C8 | 119.2 (2) |
O1—N—C10 | 119.15 (16) | C10A—C8A—C9 | 120.99 (18) |
O2—N—C10 | 117.58 (15) | C8—C8A—C9 | 119.77 (18) |
C2—C1—C9A | 120.8 (2) | O9—C9—C8A | 120.8 (2) |
C2—C1—H1 | 119.6 | O9—C9—C9A | 120.8 (2) |
C9A—C1—H1 | 119.6 | C8A—C9—C9A | 118.40 (17) |
C1—C2—C3 | 120.3 (2) | C4A—C9A—C1 | 119.5 (2) |
C1—C2—H2 | 119.8 | C4A—C9A—C9 | 121.66 (18) |
C3—C2—H2 | 119.8 | C1—C9A—C9 | 118.87 (19) |
C4—C3—C2 | 119.9 (2) | C4A—C10—C10A | 115.12 (15) |
C4—C3—H3 | 120.1 | C4A—C10—C11 | 110.91 (15) |
C2—C3—H3 | 120.1 | C10A—C10—C11 | 111.18 (15) |
C3—C4—C4A | 120.3 (2) | C4A—C10—N | 105.39 (14) |
C3—C4—H4 | 119.9 | C10A—C10—N | 105.02 (14) |
C4A—C4—H4 | 119.9 | C11—C10—N | 108.71 (13) |
C9A—C4A—C4 | 119.27 (19) | C5—C10A—C8A | 118.55 (18) |
C9A—C4A—C10 | 121.27 (18) | C5—C10A—C10 | 119.39 (16) |
C4—C4A—C10 | 119.42 (18) | C8A—C10A—C10 | 122.03 (17) |
C10A—C5—C6 | 121.3 (2) | C12—C11—C10 | 112.29 (14) |
C10A—C5—H5 | 119.3 | C12—C11—H11A | 109.1 |
C6—C5—H5 | 119.3 | C10—C11—H11A | 109.1 |
C7—C6—C5 | 120.1 (2) | C12—C11—H11B | 109.1 |
C7—C6—H6 | 120 | C10—C11—H11B | 109.1 |
C5—C6—H6 | 120 | H11A—C11—H11B | 107.9 |
C8—C7—C6 | 119.8 (2) | C12i—C12—C11 | 111.84 (18) |
C8—C7—H7 | 120.1 | C12i—C12—H12A | 109.2 |
C6—C7—H7 | 120.1 | C11—C12—H12A | 109.2 |
C7—C8—C8A | 121.0 (2) | C12i—C12—H12B | 109.2 |
C7—C8—H8 | 119.5 | C11—C12—H12B | 109.2 |
C8A—C8—H8 | 119.5 | H12A—C12—H12B | 107.9 |
C9A—C1—C2—C3 | −1.2 (4) | C9A—C4A—C10—C11 | 119.38 (18) |
C1—C2—C3—C4 | 1.2 (4) | C4—C4A—C10—C11 | −58.3 (2) |
C2—C3—C4—C4A | 0.0 (4) | C9A—C4A—C10—N | −123.15 (18) |
C3—C4—C4A—C9A | −1.3 (3) | C4—C4A—C10—N | 59.1 (2) |
C3—C4—C4A—C10 | 176.42 (19) | O1—N—C10—C4A | −117.6 (2) |
C10A—C5—C6—C7 | 1.1 (3) | O2—N—C10—C4A | 63.0 (2) |
C5—C6—C7—C8 | −1.1 (4) | O1—N—C10—C10A | 120.46 (19) |
C6—C7—C8—C8A | −0.1 (3) | O2—N—C10—C10A | −59.0 (2) |
C7—C8—C8A—C10A | 1.3 (3) | O1—N—C10—C11 | 1.4 (2) |
C7—C8—C8A—C9 | −176.5 (2) | O2—N—C10—C11 | −178.02 (18) |
C10A—C8A—C9—O9 | −176.35 (19) | C6—C5—C10A—C8A | 0.1 (3) |
C8—C8A—C9—O9 | 1.4 (3) | C6—C5—C10A—C10 | −178.34 (19) |
C10A—C8A—C9—C9A | 1.5 (3) | C8—C8A—C10A—C5 | −1.3 (3) |
C8—C8A—C9—C9A | 179.29 (18) | C9—C8A—C10A—C5 | 176.49 (17) |
C4—C4A—C9A—C1 | 1.4 (3) | C8—C8A—C10A—C10 | 177.10 (17) |
C10—C4A—C9A—C1 | −176.31 (17) | C9—C8A—C10A—C10 | −5.1 (3) |
C4—C4A—C9A—C9 | −177.30 (18) | C4A—C10—C10A—C5 | −173.55 (17) |
C10—C4A—C9A—C9 | 5.0 (3) | C11—C10—C10A—C5 | 59.3 (2) |
C2—C1—C9A—C4A | −0.2 (3) | N—C10—C10A—C5 | −58.1 (2) |
C2—C1—C9A—C9 | 178.6 (2) | C4A—C10—C10A—C8A | 8.1 (2) |
O9—C9—C9A—C4A | 176.39 (19) | C11—C10—C10A—C8A | −119.13 (18) |
C8A—C9—C9A—C4A | −1.5 (3) | N—C10—C10A—C8A | 123.48 (17) |
O9—C9—C9A—C1 | −2.3 (3) | C4A—C10—C11—C12 | −63.0 (2) |
C8A—C9—C9A—C1 | 179.81 (17) | C10A—C10—C11—C12 | 66.42 (19) |
C9A—C4A—C10—C10A | −7.9 (2) | N—C10—C11—C12 | −178.46 (15) |
C4—C4A—C10—C10A | 174.35 (17) | C10—C11—C12—C12i | 178.83 (18) |
Symmetry code: (i) −x, −y, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1···O9ii | 0.93 | 2.64 | 3.118 (3) | 112 |
Symmetry code: (ii) −x+1, −y, −z+1. |
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