Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806035033/ac2042sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806035033/ac2042Isup2.hkl |
CCDC reference: 623959
Key indicators
- Single-crystal X-ray study
- T = 113 K
- Mean (C-C) = 0.002 Å
- R factor = 0.045
- wR factor = 0.129
- Data-to-parameter ratio = 17.1
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 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 0 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 0 ALERT type 5 Informative message, check
Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: CrystalStructure (Rigaku/MSC, 2005); software used to prepare material for publication: CrystalStructure.
C13H13NO3 | Dx = 1.362 Mg m−3 |
Mr = 231.24 | Melting point = 373–374 K |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71070 Å |
a = 10.5944 (14) Å | Cell parameters from 3251 reflections |
b = 11.2733 (15) Å | θ = 1.9–27.9° |
c = 9.5282 (10) Å | µ = 0.10 mm−1 |
β = 97.703 (6)° | T = 113 K |
V = 1127.7 (2) Å3 | Block, colorless |
Z = 4 | 0.18 × 0.16 × 0.14 mm |
F(000) = 488 |
Rigaku Saturn diffractometer | 2667 independent reflections |
Radiation source: rotating anode | 1760 reflections with I > 2σ(I) |
Confocal monochromator | Rint = 0.050 |
Detector resolution: 7.31 pixels mm-1 | θmax = 27.9°, θmin = 1.9° |
ω scans | h = −13→13 |
Absorption correction: multi-scan (Jacobson, 1998) | k = −13→14 |
Tmin = 0.980, Tmax = 0.987 | l = −11→12 |
10401 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.045 | H-atom parameters constrained |
wR(F2) = 0.129 | w = 1/[σ2(Fo2) + (0.0711P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
2667 reflections | Δρmax = 0.28 e Å−3 |
156 parameters | Δρmin = −0.32 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.069 (8) |
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. |
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 | Occ. (<1) | |
O1 | 0.50502 (13) | 0.46620 (10) | 0.18915 (12) | 0.0351 (4) | |
O2 | 0.06730 (13) | 0.48419 (10) | 0.66631 (13) | 0.0367 (4) | |
O3 | −0.06571 (12) | 0.61662 (11) | 0.72173 (14) | 0.0394 (4) | |
N1 | 0.02824 (14) | 0.58726 (12) | 0.66747 (14) | 0.0267 (3) | |
C1 | 0.50358 (16) | 0.54733 (13) | 0.27435 (16) | 0.0218 (4) | |
C2 | 0.38666 (15) | 0.57114 (13) | 0.34539 (16) | 0.0210 (4) | |
H2A | 0.3887 | 0.5197 | 0.4299 | 0.025* | |
H2B | 0.3095 | 0.5508 | 0.2792 | 0.025* | |
C3 | 0.37903 (14) | 0.70068 (12) | 0.39011 (15) | 0.0181 (3) | |
H3 | 0.3721 | 0.7501 | 0.3023 | 0.022* | |
C4 | 0.50345 (14) | 0.73570 (13) | 0.48312 (15) | 0.0189 (3) | |
H4A | 0.5024 | 0.8220 | 0.5021 | 0.023* | |
H4B | 0.5085 | 0.6938 | 0.5750 | 0.023* | |
C5 | 0.61939 (15) | 0.70601 (13) | 0.41450 (16) | 0.0207 (4) | |
C6 | 0.61593 (15) | 0.62027 (13) | 0.31656 (16) | 0.0216 (4) | |
H6 | 0.6900 | 0.6064 | 0.2727 | 0.026* | |
C7 | 0.26540 (14) | 0.72985 (13) | 0.46543 (15) | 0.0188 (3) | |
C8 | 0.19697 (14) | 0.64410 (13) | 0.52789 (15) | 0.0199 (3) | |
H8 | 0.2170 | 0.5624 | 0.5204 | 0.024* | |
C9 | 0.09887 (15) | 0.67953 (13) | 0.60149 (15) | 0.0207 (4) | |
C10 | 0.06556 (15) | 0.79655 (13) | 0.61639 (16) | 0.0228 (4) | |
H10 | −0.0015 | 0.8182 | 0.6682 | 0.027* | |
C11 | 0.13396 (15) | 0.88182 (13) | 0.55250 (17) | 0.0240 (4) | |
H11 | 0.1128 | 0.9633 | 0.5596 | 0.029* | |
C12 | 0.23220 (15) | 0.84919 (13) | 0.47888 (16) | 0.0216 (4) | |
H12 | 0.2781 | 0.9088 | 0.4366 | 0.026* | |
C13 | 0.73704 (16) | 0.77584 (15) | 0.46352 (18) | 0.0305 (4) | |
H13A | 0.7188 | 0.8337 | 0.5349 | 0.037* | 0.50 |
H13B | 0.7649 | 0.8176 | 0.3828 | 0.037* | 0.50 |
H13C | 0.8046 | 0.7220 | 0.5050 | 0.037* | 0.50 |
H13D | 0.8067 | 0.7485 | 0.4136 | 0.037* | 0.50 |
H13E | 0.7606 | 0.7646 | 0.5657 | 0.037* | 0.50 |
H13F | 0.7209 | 0.8602 | 0.4435 | 0.037* | 0.50 |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0436 (9) | 0.0294 (7) | 0.0353 (7) | −0.0001 (6) | 0.0162 (6) | −0.0123 (5) |
O2 | 0.0347 (8) | 0.0261 (7) | 0.0517 (8) | 0.0005 (5) | 0.0152 (6) | 0.0101 (6) |
O3 | 0.0294 (8) | 0.0473 (8) | 0.0465 (8) | 0.0031 (6) | 0.0234 (6) | 0.0087 (6) |
N1 | 0.0217 (8) | 0.0320 (8) | 0.0270 (7) | −0.0008 (6) | 0.0060 (6) | 0.0042 (6) |
C1 | 0.0265 (9) | 0.0192 (7) | 0.0203 (8) | 0.0042 (6) | 0.0054 (7) | 0.0026 (6) |
C2 | 0.0219 (9) | 0.0212 (8) | 0.0198 (8) | −0.0005 (6) | 0.0028 (6) | −0.0018 (6) |
C3 | 0.0183 (8) | 0.0183 (7) | 0.0182 (7) | 0.0002 (6) | 0.0045 (6) | 0.0019 (6) |
C4 | 0.0207 (8) | 0.0173 (7) | 0.0191 (8) | 0.0004 (6) | 0.0042 (6) | 0.0006 (6) |
C5 | 0.0194 (8) | 0.0212 (8) | 0.0217 (8) | 0.0016 (6) | 0.0040 (6) | 0.0076 (6) |
C6 | 0.0217 (9) | 0.0234 (8) | 0.0213 (8) | 0.0039 (6) | 0.0085 (7) | 0.0052 (6) |
C7 | 0.0173 (8) | 0.0206 (7) | 0.0178 (7) | 0.0004 (6) | 0.0005 (6) | −0.0015 (6) |
C8 | 0.0175 (8) | 0.0189 (7) | 0.0230 (8) | 0.0004 (6) | 0.0016 (6) | −0.0001 (6) |
C9 | 0.0185 (8) | 0.0243 (8) | 0.0194 (8) | −0.0017 (6) | 0.0027 (6) | 0.0026 (6) |
C10 | 0.0164 (8) | 0.0277 (8) | 0.0245 (8) | 0.0022 (6) | 0.0033 (6) | −0.0057 (6) |
C11 | 0.0188 (9) | 0.0210 (8) | 0.0316 (9) | 0.0027 (6) | 0.0014 (7) | −0.0046 (7) |
C12 | 0.0199 (9) | 0.0199 (7) | 0.0246 (8) | −0.0015 (6) | 0.0014 (7) | 0.0000 (6) |
C13 | 0.0195 (9) | 0.0357 (9) | 0.0367 (10) | −0.0033 (7) | 0.0056 (8) | −0.0019 (7) |
O1—C1 | 1.2244 (17) | C6—H6 | 0.9500 |
O2—N1 | 1.2339 (17) | C7—C8 | 1.389 (2) |
O3—N1 | 1.2270 (17) | C7—C12 | 1.401 (2) |
N1—C9 | 1.4708 (19) | C8—C9 | 1.388 (2) |
C1—C6 | 1.458 (2) | C8—H8 | 0.9500 |
C1—C2 | 1.513 (2) | C9—C10 | 1.378 (2) |
C2—C3 | 1.526 (2) | C10—C11 | 1.392 (2) |
C2—H2A | 0.9900 | C10—H10 | 0.9500 |
C2—H2B | 0.9900 | C11—C12 | 1.381 (2) |
C3—C7 | 1.518 (2) | C11—H11 | 0.9500 |
C3—C4 | 1.538 (2) | C12—H12 | 0.9500 |
C3—H3 | 1.0000 | C13—H13A | 0.9800 |
C4—C5 | 1.504 (2) | C13—H13B | 0.9800 |
C4—H4A | 0.9900 | C13—H13C | 0.9800 |
C4—H4B | 0.9900 | C13—H13D | 0.9800 |
C5—C6 | 1.341 (2) | C13—H13E | 0.9800 |
C5—C13 | 1.495 (2) | C13—H13F | 0.9800 |
O3—N1—O2 | 123.35 (13) | C7—C8—H8 | 120.5 |
O3—N1—C9 | 118.50 (13) | C10—C9—C8 | 123.16 (14) |
O2—N1—C9 | 118.14 (13) | C10—C9—N1 | 118.76 (13) |
O1—C1—C6 | 121.46 (14) | C8—C9—N1 | 118.08 (13) |
O1—C1—C2 | 120.85 (15) | C9—C10—C11 | 117.42 (14) |
C6—C1—C2 | 117.61 (13) | C9—C10—H10 | 121.3 |
C1—C2—C3 | 111.82 (13) | C11—C10—H10 | 121.3 |
C1—C2—H2A | 109.3 | C12—C11—C10 | 120.68 (14) |
C3—C2—H2A | 109.3 | C12—C11—H11 | 119.7 |
C1—C2—H2B | 109.3 | C10—C11—H11 | 119.7 |
C3—C2—H2B | 109.3 | C11—C12—C7 | 121.20 (14) |
H2A—C2—H2B | 107.9 | C11—C12—H12 | 119.4 |
C7—C3—C2 | 114.48 (12) | C7—C12—H12 | 119.4 |
C7—C3—C4 | 110.17 (11) | C5—C13—H13A | 109.5 |
C2—C3—C4 | 109.45 (12) | C5—C13—H13B | 109.5 |
C7—C3—H3 | 107.5 | H13A—C13—H13B | 109.5 |
C2—C3—H3 | 107.5 | C5—C13—H13C | 109.5 |
C4—C3—H3 | 107.5 | H13A—C13—H13C | 109.5 |
C5—C4—C3 | 112.28 (12) | H13B—C13—H13C | 109.5 |
C5—C4—H4A | 109.1 | C5—C13—H13D | 109.5 |
C3—C4—H4A | 109.1 | H13A—C13—H13D | 141.1 |
C5—C4—H4B | 109.1 | H13B—C13—H13D | 56.3 |
C3—C4—H4B | 109.1 | H13C—C13—H13D | 56.3 |
H4A—C4—H4B | 107.9 | C5—C13—H13E | 109.5 |
C6—C5—C13 | 122.75 (14) | H13A—C13—H13E | 56.3 |
C6—C5—C4 | 121.01 (14) | H13B—C13—H13E | 141.1 |
C13—C5—C4 | 116.24 (13) | H13C—C13—H13E | 56.3 |
C5—C6—C1 | 122.94 (14) | H13D—C13—H13E | 109.5 |
C5—C6—H6 | 118.5 | C5—C13—H13F | 109.5 |
C1—C6—H6 | 118.5 | H13A—C13—H13F | 56.3 |
C8—C7—C12 | 118.50 (13) | H13B—C13—H13F | 56.3 |
C8—C7—C3 | 122.98 (13) | H13C—C13—H13F | 141.1 |
C12—C7—C3 | 118.44 (13) | H13D—C13—H13F | 109.5 |
C9—C8—C7 | 119.03 (14) | H13E—C13—H13F | 109.5 |
C9—C8—H8 | 120.5 | ||
O1—C1—C2—C3 | −153.78 (14) | C4—C3—C7—C12 | 71.86 (17) |
C6—C1—C2—C3 | 29.34 (19) | C12—C7—C8—C9 | −0.2 (2) |
C1—C2—C3—C7 | −178.56 (13) | C3—C7—C8—C9 | 176.37 (13) |
C1—C2—C3—C4 | −54.33 (16) | C7—C8—C9—C10 | −0.2 (2) |
C7—C3—C4—C5 | 178.71 (12) | C7—C8—C9—N1 | −179.64 (14) |
C2—C3—C4—C5 | 51.99 (15) | O3—N1—C9—C10 | 7.0 (2) |
C3—C4—C5—C6 | −24.32 (19) | O2—N1—C9—C10 | −172.49 (15) |
C3—C4—C5—C13 | 156.60 (13) | O3—N1—C9—C8 | −173.56 (15) |
C13—C5—C6—C1 | 176.35 (15) | O2—N1—C9—C8 | 7.0 (2) |
C4—C5—C6—C1 | −2.7 (2) | C8—C9—C10—C11 | 0.7 (2) |
O1—C1—C6—C5 | −176.73 (14) | N1—C9—C10—C11 | −179.87 (14) |
C2—C1—C6—C5 | 0.1 (2) | C9—C10—C11—C12 | −0.8 (2) |
C2—C3—C7—C8 | 19.1 (2) | C10—C11—C12—C7 | 0.4 (2) |
C4—C3—C7—C8 | −104.73 (16) | C8—C7—C12—C11 | 0.1 (2) |
C2—C3—C7—C12 | −164.30 (13) | C3—C7—C12—C11 | −176.66 (14) |