Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806013560/lh2034sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806013560/lh2034Isup2.hkl |
CCDC reference: 608445
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.003 Å
- R factor = 0.048
- wR factor = 0.118
- Data-to-parameter ratio = 13.2
checkCIF/PLATON results
No syntax errors found
Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.809 0.975 Tmin(prime) and Tmax expected: 0.962 0.976 RR(prime) = 0.842 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.84
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 0 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 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CrysAlis CCD (Oxford Diffraction, 2005); cell refinement: CrysAlis RED (Oxford Diffraction, 2005); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
C10H11NO2 | F(000) = 376 |
Mr = 177.20 | Dx = 1.265 Mg m−3 |
Monoclinic, P21/c | Melting point: 349 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 7.765 (7) Å | Cell parameters from 5840 reflections |
b = 8.699 (7) Å | θ = 3.8–32.9° |
c = 15.805 (13) Å | µ = 0.09 mm−1 |
β = 119.35 (7)° | T = 298 K |
V = 930.6 (14) Å3 | Needle, orange |
Z = 4 | 0.43 × 0.31 × 0.27 mm |
Oxford Diffraction Sapphire3 diffractometer | 1639 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 1019 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.036 |
Detector resolution: 16.1790 pixels mm-1 | θmax = 25.0°, θmin = 3.8° |
ω scans | h = −9→9 |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2005)' | k = −10→10 |
Tmin = 0.809, Tmax = 0.975 | l = −18→18 |
19878 measured reflections |
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) = 0.118 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.93 | w = 1/[σ2(Fo2) + (0.0807P)2] where P = (Fo2 + 2Fc2)/3 |
1639 reflections | (Δ/σ)max < 0.001 |
124 parameters | Δρmax = 0.18 e Å−3 |
0 restraints | Δρmin = −0.26 e Å−3 |
Experimental. Spectroscopic analysis: Rf = 0.46 (Al2O3, 80% hexanes/20% ethyl acetate); m.p. 349 K; IR (nujol, ν, cm-1): 3222, 3065, 1687, 1652, 1584, 1529, 1454, 1251, 765, 723; 1H NMR (400 MHz, CDCl3, δ, p.p.m.): 11.706 (s, 1H), 8.735 (dd, 1H, J = 8.3 and 0.9 Hz), 7.888 (dd, 1H, J = 7.8 and 1.4 Hz), 7.546 (dt, 1H, J = 8.3 and 1.4 Hz), 7.104 (dt, 1H, J = 7.8 and 0.9 Hz), 2.661 (s, 3H), 2.222 (s, 3H); 13C NMR (400 MHz, CDCl3, δ, p.p.m.): 202.94, 169.96, 141.09, 135.26, 131.67, 122.39, 121.78, 120.83, 28.72, 25.69; UV–Vis (CH2Cl2; λmax, logε): 326 nm, 3.72; EI–MS calculated for C10H11NO2: M+ 177; found: 177. During model refinement, H atoms bonded to C atoms were placed in calculated postions with C—H = 0.93 or C—H = 0.96 Å (for methyl groups) and included in the refinement in a riding-model approximation with Uiso(H) = either 1.2Ueq(C) or 1.5Ueq(C) for methyl H atoms. The H atom bonded to N was refined independently with an isotropic displacement parameter. |
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 | ||
O1 | 0.44758 (18) | 0.62062 (15) | 1.16119 (8) | 0.0760 (4) | |
C2 | 0.3075 (2) | 0.69817 (19) | 1.10181 (12) | 0.0564 (5) | |
C1 | 0.2635 (3) | 0.8482 (2) | 1.13399 (15) | 0.0837 (6) | |
H1A | 0.3648 | 0.8701 | 1.1992 | 0.126* | |
H1B | 0.1380 | 0.8418 | 1.1318 | 0.126* | |
H1C | 0.2596 | 0.9288 | 1.0916 | 0.126* | |
C3 | 0.1809 (2) | 0.64701 (18) | 0.99938 (10) | 0.0491 (4) | |
C4 | 0.0316 (2) | 0.7457 (2) | 0.93336 (11) | 0.0636 (5) | |
H4 | 0.0113 | 0.8391 | 0.9557 | 0.076* | |
C5 | −0.0850 (2) | 0.7088 (2) | 0.83715 (13) | 0.0733 (6) | |
H5 | −0.1831 | 0.7759 | 0.7953 | 0.088* | |
C6 | −0.0546 (3) | 0.5712 (3) | 0.80362 (12) | 0.0744 (6) | |
H6 | −0.1309 | 0.5468 | 0.7382 | 0.089* | |
C7 | 0.0878 (2) | 0.4684 (2) | 0.86553 (11) | 0.0629 (5) | |
H7 | 0.1050 | 0.3755 | 0.8415 | 0.075* | |
C8 | 0.2056 (2) | 0.50359 (18) | 0.96393 (10) | 0.0488 (4) | |
N1 | 0.35145 (18) | 0.40136 (16) | 1.02846 (10) | 0.0521 (4) | |
C9 | 0.3767 (2) | 0.2500 (2) | 1.01831 (12) | 0.0581 (4) | |
O2 | 0.2685 (2) | 0.17495 (16) | 0.94641 (10) | 0.1004 (5) | |
C10 | 0.5472 (3) | 0.1773 (2) | 1.10576 (12) | 0.0672 (5) | |
H10A | 0.5074 | 0.1528 | 1.1529 | 0.101* | |
H10B | 0.6562 | 0.2478 | 1.1336 | 0.101* | |
H10C | 0.5866 | 0.0850 | 1.0865 | 0.101* | |
H1 | 0.423 (2) | 0.443 (2) | 1.0867 (12) | 0.064 (5)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0757 (8) | 0.0732 (9) | 0.0541 (7) | 0.0048 (6) | 0.0124 (6) | −0.0073 (6) |
C2 | 0.0643 (11) | 0.0505 (10) | 0.0561 (10) | −0.0087 (8) | 0.0308 (9) | −0.0010 (8) |
C1 | 0.1073 (16) | 0.0580 (12) | 0.0802 (13) | −0.0036 (11) | 0.0415 (12) | −0.0104 (10) |
C3 | 0.0458 (9) | 0.0539 (10) | 0.0489 (9) | −0.0031 (7) | 0.0241 (7) | 0.0052 (7) |
C4 | 0.0600 (10) | 0.0667 (12) | 0.0662 (11) | 0.0067 (9) | 0.0326 (9) | 0.0126 (9) |
C5 | 0.0542 (11) | 0.0897 (15) | 0.0648 (12) | 0.0091 (10) | 0.0203 (9) | 0.0228 (11) |
C6 | 0.0625 (12) | 0.0962 (16) | 0.0466 (9) | −0.0153 (11) | 0.0129 (9) | 0.0056 (10) |
C7 | 0.0659 (11) | 0.0677 (12) | 0.0480 (9) | −0.0113 (9) | 0.0224 (8) | −0.0037 (8) |
C8 | 0.0441 (8) | 0.0555 (10) | 0.0472 (8) | −0.0071 (7) | 0.0226 (7) | 0.0034 (7) |
N1 | 0.0562 (8) | 0.0490 (9) | 0.0459 (8) | −0.0035 (6) | 0.0210 (7) | −0.0009 (6) |
C9 | 0.0623 (10) | 0.0544 (11) | 0.0608 (10) | −0.0014 (8) | 0.0328 (9) | −0.0051 (9) |
O2 | 0.1082 (11) | 0.0686 (9) | 0.0853 (10) | 0.0103 (8) | 0.0171 (8) | −0.0232 (8) |
C10 | 0.0752 (12) | 0.0581 (11) | 0.0718 (11) | 0.0057 (9) | 0.0387 (10) | 0.0094 (9) |
O1—C2 | 1.232 (2) | C6—C7 | 1.385 (3) |
C2—C3 | 1.492 (3) | C6—H6 | 0.9300 |
C2—C1 | 1.500 (3) | C7—C8 | 1.398 (3) |
C1—H1A | 0.9600 | C7—H7 | 0.9300 |
C1—H1B | 0.9600 | C8—N1 | 1.408 (2) |
C1—H1C | 0.9600 | N1—C9 | 1.352 (2) |
C3—C4 | 1.409 (2) | N1—H1 | 0.888 (17) |
C3—C8 | 1.419 (2) | C9—O2 | 1.220 (2) |
C4—C5 | 1.373 (3) | C9—C10 | 1.506 (3) |
C4—H4 | 0.9300 | C10—H10A | 0.9600 |
C5—C6 | 1.375 (3) | C10—H10B | 0.9600 |
C5—H5 | 0.9300 | C10—H10C | 0.9600 |
O1—C2—C3 | 121.95 (17) | C7—C6—H6 | 119.4 |
O1—C2—C1 | 118.75 (17) | C6—C7—C8 | 120.34 (19) |
C3—C2—C1 | 119.29 (16) | C6—C7—H7 | 119.8 |
C2—C1—H1A | 109.5 | C8—C7—H7 | 119.8 |
C2—C1—H1B | 109.5 | C7—C8—N1 | 121.55 (17) |
H1A—C1—H1B | 109.5 | C7—C8—C3 | 119.36 (14) |
C2—C1—H1C | 109.5 | N1—C8—C3 | 119.08 (14) |
H1A—C1—H1C | 109.5 | C9—N1—C8 | 129.88 (15) |
H1B—C1—H1C | 109.5 | C9—N1—H1 | 118.0 (11) |
C4—C3—C8 | 117.71 (15) | C8—N1—H1 | 111.4 (11) |
C4—C3—C2 | 119.17 (17) | O2—C9—N1 | 123.91 (17) |
C8—C3—C2 | 123.11 (14) | O2—C9—C10 | 121.64 (18) |
C5—C4—C3 | 122.30 (19) | N1—C9—C10 | 114.40 (15) |
C5—C4—H4 | 118.8 | C9—C10—H10A | 109.5 |
C3—C4—H4 | 118.8 | C9—C10—H10B | 109.5 |
C4—C5—C6 | 119.05 (17) | H10A—C10—H10B | 109.5 |
C4—C5—H5 | 120.5 | C9—C10—H10C | 109.5 |
C6—C5—H5 | 120.5 | H10A—C10—H10C | 109.5 |
C5—C6—C7 | 121.19 (17) | H10B—C10—H10C | 109.5 |
C5—C6—H6 | 119.4 | ||
O1—C2—C3—C4 | −175.63 (15) | C6—C7—C8—C3 | −1.3 (2) |
C1—C2—C3—C4 | 4.4 (2) | C4—C3—C8—C7 | 2.4 (2) |
O1—C2—C3—C8 | 3.1 (2) | C2—C3—C8—C7 | −176.39 (14) |
C1—C2—C3—C8 | −176.83 (14) | C4—C3—C8—N1 | −179.00 (13) |
C8—C3—C4—C5 | −1.5 (2) | C2—C3—C8—N1 | 2.3 (2) |
C2—C3—C4—C5 | 177.30 (14) | C7—C8—N1—C9 | −16.6 (2) |
C3—C4—C5—C6 | −0.5 (3) | C3—C8—N1—C9 | 164.75 (14) |
C4—C5—C6—C7 | 1.6 (3) | C8—N1—C9—O2 | 0.0 (3) |
C5—C6—C7—C8 | −0.7 (3) | C8—N1—C9—C10 | −177.64 (14) |
C6—C7—C8—N1 | −179.94 (13) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1 | 0.888 (17) | 1.893 (18) | 2.657 (2) | 143.1 (15) |
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