Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805013772/wn6351sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805013772/wn6351Isup2.hkl |
CCDC reference: 274662
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.048
- wR factor = 0.140
- Data-to-parameter ratio = 16.4
checkCIF/PLATON results
No syntax errors found
Alert level A DIFF020_ALERT_1_A _diffrn_standards_interval_count and _diffrn_standards_interval_time are missing. Number of measurements between standards or time (min) between standards. DIFF022_ALERT_1_A _diffrn_standards_decay_% is missing Percentage decrease in standards intensity.
Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 47 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 ..... ?
2 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 4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 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
Data collection: RAPID-AUTO (Rigaku, 2001); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.
C17H13NO3 | Dx = 1.350 Mg m−3 |
Mr = 279.28 | Melting point = 431–433 K |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
a = 11.857 (2) Å | Cell parameters from 19445 reflections |
b = 7.1867 (14) Å | θ = 1.3–27.5° |
c = 32.253 (7) Å | µ = 0.09 mm−1 |
V = 2748.5 (10) Å3 | T = 293 K |
Z = 8 | Platelet, colorless |
F(000) = 1168 | 0.49 × 0.45 × 0.04 mm |
Rigaku R-AXIS RAPID IP diffractometer | 3131 independent reflections |
Radiation source: Rotating Anode | 1471 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.054 |
ω scans | θmax = 27.5°, θmin = 1.3° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −14→15 |
Tmin = 0.955, Tmax = 0.997 | k = −8→9 |
19445 measured reflections | l = −41→40 |
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) = 0.140 | H-atom parameters constrained |
S = 0.83 | w = 1/[σ2(Fo2) + (0.0395P)2] where P = (Fo2 + 2Fc2)/3 |
3131 reflections | (Δ/σ)max < 0.001 |
191 parameters | Δρmax = 0.17 e Å−3 |
0 restraints | Δρmin = −0.32 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) 6.2618 (0.0038) x - 6.0308 (0.0019) y + 4.1950 (0.0056) z = 0.5070 (0.0045) * 0.0042 (0.0015) O1 * 0.0689 (0.0017) O2 * -0.0112 (0.0018) O3 * 0.0900 (0.0016) N1 * 0.0625 (0.0019) C1 * 0.0720 (0.0019) C2 * -0.0126 (0.0020) C3 * -0.0962 (0.0022) C4 * -0.0938 (0.0022) C5 * -0.0123 (0.0019) C6 * 0.0383 (0.0020) C7 * 0.0414 (0.0019) C8 * -0.0068 (0.0021) C9 * 0.0043 (0.0021) C10 * -0.0370 (0.0020) C11 * 0.0110 (0.0022) C12 * 0.0114 (0.0022) C13 * -0.0274 (0.0020) C14 * -0.1014 (0.0022) C15 * -0.1014 (0.0021) C16 * 0.0960 (0.0027) C17 Rms deviation of fitted atoms = 0.0601 |
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 | 0.28258 (11) | 0.5423 (2) | 0.47971 (4) | 0.0500 (4) | |
O2 | 0.25548 (15) | 0.4583 (3) | 0.41478 (5) | 0.0666 (5) | |
O3 | 0.68958 (16) | 0.7755 (3) | 0.20367 (5) | 0.0684 (5) | |
N1 | 0.48316 (14) | 0.7196 (2) | 0.45561 (5) | 0.0411 (4) | |
C1 | 0.44836 (17) | 0.7168 (3) | 0.49693 (7) | 0.0381 (5) | |
C2 | 0.51259 (19) | 0.8031 (3) | 0.52742 (7) | 0.0477 (6) | |
H2A | 0.5809 | 0.8584 | 0.5204 | 0.057* | |
C3 | 0.4763 (2) | 0.8076 (3) | 0.56777 (7) | 0.0548 (6) | |
H3A | 0.5197 | 0.8668 | 0.5878 | 0.066* | |
C4 | 0.3750 (2) | 0.7239 (4) | 0.57878 (8) | 0.0607 (7) | |
H4A | 0.3507 | 0.7273 | 0.6062 | 0.073* | |
C5 | 0.3108 (2) | 0.6364 (3) | 0.54939 (7) | 0.0558 (6) | |
H5A | 0.2431 | 0.5799 | 0.5567 | 0.067* | |
C6 | 0.34760 (17) | 0.6328 (3) | 0.50884 (7) | 0.0420 (5) | |
C7 | 0.31359 (18) | 0.5405 (3) | 0.43885 (7) | 0.0459 (5) | |
C8 | 0.41924 (17) | 0.6422 (3) | 0.42819 (6) | 0.0402 (5) | |
C9 | 0.44672 (19) | 0.6480 (3) | 0.38405 (7) | 0.0472 (5) | |
H9A | 0.3975 | 0.5909 | 0.3656 | 0.057* | |
C10 | 0.5378 (2) | 0.7302 (3) | 0.36887 (7) | 0.0476 (5) | |
H10A | 0.5855 | 0.7867 | 0.3880 | 0.057* | |
C11 | 0.57170 (18) | 0.7420 (3) | 0.32535 (6) | 0.0442 (5) | |
C12 | 0.6720 (2) | 0.8307 (3) | 0.31461 (7) | 0.0544 (6) | |
H12A | 0.7156 | 0.8850 | 0.3353 | 0.065* | |
C13 | 0.7082 (2) | 0.8401 (4) | 0.27416 (7) | 0.0564 (6) | |
H13A | 0.7753 | 0.9010 | 0.2679 | 0.068* | |
C14 | 0.6454 (2) | 0.7595 (3) | 0.24276 (7) | 0.0489 (6) | |
C15 | 0.5445 (2) | 0.6736 (3) | 0.25232 (7) | 0.0521 (6) | |
H15A | 0.5006 | 0.6217 | 0.2314 | 0.062* | |
C16 | 0.50910 (19) | 0.6652 (3) | 0.29305 (7) | 0.0517 (6) | |
H16A | 0.4412 | 0.6064 | 0.2991 | 0.062* | |
C17 | 0.6345 (3) | 0.6780 (4) | 0.17131 (8) | 0.0813 (9) | |
H17A | 0.6731 | 0.7004 | 0.1456 | 0.122* | |
H17B | 0.5580 | 0.7204 | 0.1691 | 0.122* | |
H17C | 0.6351 | 0.5471 | 0.1773 | 0.122* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0376 (9) | 0.0577 (10) | 0.0548 (9) | −0.0072 (8) | 0.0063 (7) | 0.0048 (8) |
O2 | 0.0543 (10) | 0.0779 (12) | 0.0675 (10) | −0.0233 (10) | −0.0076 (9) | −0.0051 (10) |
O3 | 0.0771 (11) | 0.0773 (13) | 0.0507 (10) | −0.0085 (10) | 0.0155 (9) | 0.0054 (9) |
N1 | 0.0361 (9) | 0.0423 (10) | 0.0450 (10) | 0.0015 (8) | 0.0030 (8) | 0.0059 (9) |
C1 | 0.0348 (11) | 0.0369 (11) | 0.0427 (11) | 0.0064 (10) | 0.0029 (9) | 0.0082 (10) |
C2 | 0.0442 (13) | 0.0477 (13) | 0.0511 (14) | 0.0007 (11) | −0.0039 (11) | 0.0069 (12) |
C3 | 0.0648 (16) | 0.0523 (14) | 0.0472 (14) | 0.0076 (13) | −0.0077 (12) | 0.0012 (12) |
C4 | 0.0712 (17) | 0.0662 (16) | 0.0448 (14) | 0.0118 (15) | 0.0114 (12) | 0.0052 (13) |
C5 | 0.0506 (13) | 0.0580 (16) | 0.0588 (15) | 0.0011 (12) | 0.0164 (12) | 0.0078 (13) |
C6 | 0.0369 (12) | 0.0414 (12) | 0.0477 (13) | 0.0032 (10) | 0.0034 (10) | 0.0045 (10) |
C7 | 0.0393 (12) | 0.0457 (13) | 0.0529 (14) | 0.0004 (11) | 0.0007 (11) | 0.0040 (11) |
C8 | 0.0348 (12) | 0.0391 (11) | 0.0468 (12) | 0.0024 (9) | 0.0013 (10) | 0.0060 (10) |
C9 | 0.0430 (12) | 0.0524 (13) | 0.0463 (12) | −0.0015 (12) | −0.0019 (10) | 0.0017 (11) |
C10 | 0.0487 (12) | 0.0484 (13) | 0.0458 (13) | −0.0021 (12) | −0.0035 (10) | 0.0005 (11) |
C11 | 0.0477 (13) | 0.0410 (12) | 0.0439 (12) | −0.0012 (11) | 0.0020 (10) | 0.0050 (10) |
C12 | 0.0554 (14) | 0.0582 (14) | 0.0496 (14) | −0.0146 (12) | −0.0024 (12) | 0.0037 (12) |
C13 | 0.0537 (14) | 0.0572 (15) | 0.0584 (15) | −0.0130 (12) | 0.0051 (12) | 0.0086 (13) |
C14 | 0.0590 (15) | 0.0440 (13) | 0.0437 (14) | 0.0018 (11) | 0.0093 (11) | 0.0071 (11) |
C15 | 0.0559 (14) | 0.0549 (13) | 0.0453 (13) | −0.0049 (12) | −0.0016 (11) | −0.0002 (12) |
C16 | 0.0495 (14) | 0.0513 (13) | 0.0542 (15) | −0.0120 (12) | 0.0053 (11) | 0.0013 (11) |
C17 | 0.102 (2) | 0.096 (2) | 0.0460 (16) | −0.003 (2) | 0.0098 (15) | −0.0074 (16) |
O1—C7 | 1.368 (2) | C8—C9 | 1.461 (3) |
O1—C6 | 1.378 (2) | C9—C10 | 1.325 (3) |
O2—C7 | 1.194 (3) | C9—H9A | 0.9300 |
O3—C14 | 1.370 (3) | C10—C11 | 1.462 (3) |
O3—C17 | 1.417 (3) | C10—H10A | 0.9300 |
N1—C8 | 1.291 (3) | C11—C16 | 1.393 (3) |
N1—C1 | 1.395 (3) | C11—C12 | 1.394 (3) |
C1—C2 | 1.390 (3) | C12—C13 | 1.375 (3) |
C1—C6 | 1.392 (3) | C12—H12A | 0.9300 |
C2—C3 | 1.371 (3) | C13—C14 | 1.384 (3) |
C2—H2A | 0.9300 | C13—H13A | 0.9300 |
C3—C4 | 1.390 (3) | C14—C15 | 1.382 (3) |
C3—H3A | 0.9300 | C15—C16 | 1.380 (3) |
C4—C5 | 1.369 (3) | C15—H15A | 0.9300 |
C4—H4A | 0.9300 | C16—H16A | 0.9300 |
C5—C6 | 1.379 (3) | C17—H17A | 0.9600 |
C5—H5A | 0.9300 | C17—H17B | 0.9600 |
C7—C8 | 1.491 (3) | C17—H17C | 0.9600 |
C7—O1—C6 | 120.72 (17) | C8—C9—H9A | 118.2 |
C14—O3—C17 | 117.4 (2) | C9—C10—C11 | 127.2 (2) |
C8—N1—C1 | 118.33 (18) | C9—C10—H10A | 116.4 |
C2—C1—C6 | 117.9 (2) | C11—C10—H10A | 116.4 |
C2—C1—N1 | 120.5 (2) | C16—C11—C12 | 116.8 (2) |
C6—C1—N1 | 121.6 (2) | C16—C11—C10 | 123.3 (2) |
C3—C2—C1 | 120.7 (2) | C12—C11—C10 | 120.0 (2) |
C3—C2—H2A | 119.7 | C13—C12—C11 | 121.6 (2) |
C1—C2—H2A | 119.7 | C13—C12—H12A | 119.2 |
C2—C3—C4 | 120.2 (2) | C11—C12—H12A | 119.2 |
C2—C3—H3A | 119.9 | C12—C13—C14 | 120.4 (2) |
C4—C3—H3A | 119.9 | C12—C13—H13A | 119.8 |
C5—C4—C3 | 120.2 (2) | C14—C13—H13A | 119.8 |
C5—C4—H4A | 119.9 | O3—C14—C15 | 125.0 (2) |
C3—C4—H4A | 119.9 | O3—C14—C13 | 115.6 (2) |
C4—C5—C6 | 119.3 (2) | C15—C14—C13 | 119.3 (2) |
C4—C5—H5A | 120.3 | C16—C15—C14 | 119.7 (2) |
C6—C5—H5A | 120.3 | C16—C15—H15A | 120.2 |
O1—C6—C5 | 118.58 (19) | C14—C15—H15A | 120.2 |
O1—C6—C1 | 119.75 (19) | C15—C16—C11 | 122.2 (2) |
C5—C6—C1 | 121.7 (2) | C15—C16—H16A | 118.9 |
O2—C7—O1 | 118.4 (2) | C11—C16—H16A | 118.9 |
O2—C7—C8 | 125.3 (2) | O3—C17—H17A | 109.5 |
O1—C7—C8 | 116.30 (19) | O3—C17—H17B | 109.5 |
N1—C8—C9 | 121.62 (19) | H17A—C17—H17B | 109.5 |
N1—C8—C7 | 123.15 (19) | O3—C17—H17C | 109.5 |
C9—C8—C7 | 115.23 (19) | H17A—C17—H17C | 109.5 |
C10—C9—C8 | 123.7 (2) | H17B—C17—H17C | 109.5 |
C10—C9—H9A | 118.2 | ||
C8—N1—C1—C2 | −178.06 (19) | O1—C7—C8—N1 | 4.0 (3) |
C8—N1—C1—C6 | 0.1 (3) | O2—C7—C8—C9 | 4.0 (3) |
C6—C1—C2—C3 | −1.1 (3) | O1—C7—C8—C9 | −176.32 (18) |
N1—C1—C2—C3 | 177.19 (19) | N1—C8—C9—C10 | 0.5 (3) |
C1—C2—C3—C4 | 0.6 (3) | C7—C8—C9—C10 | −179.2 (2) |
C2—C3—C4—C5 | 0.0 (4) | C8—C9—C10—C11 | 179.8 (2) |
C3—C4—C5—C6 | −0.2 (3) | C9—C10—C11—C16 | 0.3 (4) |
C7—O1—C6—C5 | 177.8 (2) | C9—C10—C11—C12 | −178.6 (2) |
C7—O1—C6—C1 | −2.7 (3) | C16—C11—C12—C13 | −0.8 (3) |
C4—C5—C6—O1 | 179.3 (2) | C10—C11—C12—C13 | 178.2 (2) |
C4—C5—C6—C1 | −0.3 (3) | C11—C12—C13—C14 | −0.4 (4) |
C2—C1—C6—O1 | −178.63 (19) | C17—O3—C14—C15 | −7.8 (3) |
N1—C1—C6—O1 | 3.1 (3) | C17—O3—C14—C13 | 173.4 (2) |
C2—C1—C6—C5 | 0.9 (3) | C12—C13—C14—O3 | −179.4 (2) |
N1—C1—C6—C5 | −177.4 (2) | C12—C13—C14—C15 | 1.7 (3) |
C6—O1—C7—O2 | 179.1 (2) | O3—C14—C15—C16 | 179.6 (2) |
C6—O1—C7—C8 | −0.6 (3) | C13—C14—C15—C16 | −1.6 (3) |
C1—N1—C8—C9 | 176.66 (18) | C14—C15—C16—C11 | 0.4 (3) |
C1—N1—C8—C7 | −3.7 (3) | C12—C11—C16—C15 | 0.8 (3) |
O2—C7—C8—N1 | −175.6 (2) | C10—C11—C16—C15 | −178.1 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2A···O1i | 0.93 | 2.50 | 3.397 (3) | 163 |
Symmetry code: (i) x+1/2, −y+3/2, −z+1. |
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