


Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536810034574/cv2749sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536810034574/cv2749Isup2.hkl |
CCDC reference: 797721
Key indicators
- Single-crystal X-ray study
- T = 290 K
- Mean
(C-C) = 0.002 Å
- R factor = 0.045
- wR factor = 0.140
- Data-to-parameter ratio = 17.5
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) ..... 4 PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L= 0.600 7
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 1 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
The title compound was prepared according to the literature (Hester et al., 1967). Colourless single crystals suitable for X-ray diffraction were cultured from a solution of 95% alcohol by slow evaporation at room temperature.
All H atoms were posioned geometrically and refined using a rding model, with C—H = 0.93–0.97 Å, O—H = 0.82 Å, and with Uiso(H) = 1.2 or 1.5 Ueq(C, O).
Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).
![]() | Fig. 1. The molecular structure of the title compound showing the atomic numbering. Displacement ellipsoids of non-H atoms are drawn at the 30% probalility level. |
C11H13NO2 | F(000) = 408 |
Mr = 191.22 | Dx = 1.284 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 6826 reflections |
a = 8.185 (6) Å | θ = 3.1–27.5° |
b = 15.878 (10) Å | µ = 0.09 mm−1 |
c = 8.053 (5) Å | T = 290 K |
β = 109.02 (3)° | Block, colourless |
V = 989.4 (11) Å3 | 0.12 × 0.11 × 0.09 mm |
Z = 4 |
Rigaku R-AXIS RAPID diffractometer | 2260 independent reflections |
Radiation source: fine-focus sealed tube | 1724 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.024 |
ω scans | θmax = 27.5°, θmin = 3.3° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −10→9 |
Tmin = 0.989, Tmax = 0.992 | k = −20→20 |
9568 measured reflections | l = −10→10 |
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)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.140 | H-atom parameters constrained |
S = 1.10 | w = 1/[σ2(Fo2) + (0.0809P)2 + 0.0477P] where P = (Fo2 + 2Fc2)/3 |
2260 reflections | (Δ/σ)max = 0.022 |
129 parameters | Δρmax = 0.14 e Å−3 |
0 restraints | Δρmin = −0.20 e Å−3 |
C11H13NO2 | V = 989.4 (11) Å3 |
Mr = 191.22 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 8.185 (6) Å | µ = 0.09 mm−1 |
b = 15.878 (10) Å | T = 290 K |
c = 8.053 (5) Å | 0.12 × 0.11 × 0.09 mm |
β = 109.02 (3)° |
Rigaku R-AXIS RAPID diffractometer | 2260 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 1724 reflections with I > 2σ(I) |
Tmin = 0.989, Tmax = 0.992 | Rint = 0.024 |
9568 measured reflections |
R[F2 > 2σ(F2)] = 0.045 | 0 restraints |
wR(F2) = 0.140 | H-atom parameters constrained |
S = 1.10 | Δρmax = 0.14 e Å−3 |
2260 reflections | Δρmin = −0.20 e Å−3 |
129 parameters |
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 | ||
C1 | 0.22438 (15) | 0.07109 (8) | 0.84267 (17) | 0.0453 (3) | |
C2 | 0.19968 (18) | 0.05982 (10) | 0.65136 (18) | 0.0588 (4) | |
H2A | 0.0874 | 0.0819 | 0.5831 | 0.071* | |
H2B | 0.2007 | 0.0001 | 0.6260 | 0.071* | |
C3 | 0.33762 (19) | 0.10345 (11) | 0.59483 (18) | 0.0660 (4) | |
H3A | 0.3314 | 0.0837 | 0.4790 | 0.079* | |
H3B | 0.3160 | 0.1636 | 0.5874 | 0.079* | |
C4 | 0.51630 (18) | 0.08688 (11) | 0.72171 (18) | 0.0601 (4) | |
H4A | 0.5418 | 0.0272 | 0.7225 | 0.072* | |
H4B | 0.6009 | 0.1170 | 0.6836 | 0.072* | |
C5 | 0.52944 (15) | 0.11461 (7) | 0.90409 (15) | 0.0421 (3) | |
C6 | 0.38514 (15) | 0.10886 (7) | 0.95932 (15) | 0.0408 (3) | |
C7 | 0.39938 (17) | 0.13786 (8) | 1.12760 (17) | 0.0518 (3) | |
H7 | 0.3033 | 0.1355 | 1.1650 | 0.062* | |
C8 | 0.55144 (17) | 0.16968 (9) | 1.23853 (18) | 0.0545 (4) | |
H8 | 0.5583 | 0.1883 | 1.3501 | 0.065* | |
C9 | 0.69544 (15) | 0.17400 (8) | 1.18325 (16) | 0.0466 (3) | |
C10 | 0.68406 (15) | 0.14690 (8) | 1.01691 (16) | 0.0454 (3) | |
H10 | 0.7803 | 0.1502 | 0.9799 | 0.055* | |
C11 | 0.98486 (18) | 0.22289 (12) | 1.2455 (2) | 0.0728 (5) | |
H11A | 1.0245 | 0.1709 | 1.2110 | 0.109* | |
H11B | 1.0762 | 0.2478 | 1.3397 | 0.109* | |
H11C | 0.9512 | 0.2608 | 1.1472 | 0.109* | |
N1 | 0.11395 (13) | 0.04621 (7) | 0.91439 (15) | 0.0541 (3) | |
O1 | −0.03579 (13) | 0.01124 (8) | 0.79076 (14) | 0.0707 (4) | |
H1 | −0.0958 | −0.0108 | 0.8427 | 0.106* | |
O2 | 0.84142 (12) | 0.20688 (7) | 1.30220 (13) | 0.0634 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0398 (6) | 0.0452 (6) | 0.0489 (7) | −0.0035 (5) | 0.0115 (5) | −0.0013 (5) |
C2 | 0.0542 (8) | 0.0699 (9) | 0.0462 (7) | −0.0122 (7) | 0.0077 (6) | −0.0058 (6) |
C3 | 0.0646 (9) | 0.0886 (11) | 0.0403 (7) | −0.0151 (8) | 0.0110 (6) | −0.0007 (7) |
C4 | 0.0559 (8) | 0.0813 (10) | 0.0469 (8) | −0.0102 (7) | 0.0219 (6) | −0.0115 (7) |
C5 | 0.0415 (6) | 0.0433 (6) | 0.0406 (6) | −0.0005 (5) | 0.0122 (5) | 0.0015 (5) |
C6 | 0.0397 (6) | 0.0397 (6) | 0.0420 (6) | −0.0028 (5) | 0.0117 (5) | 0.0004 (5) |
C7 | 0.0469 (7) | 0.0615 (8) | 0.0516 (8) | −0.0096 (6) | 0.0224 (6) | −0.0074 (6) |
C8 | 0.0546 (7) | 0.0654 (9) | 0.0454 (7) | −0.0120 (6) | 0.0190 (6) | −0.0117 (6) |
C9 | 0.0419 (6) | 0.0481 (7) | 0.0453 (7) | −0.0054 (5) | 0.0081 (5) | 0.0001 (5) |
C10 | 0.0374 (6) | 0.0529 (7) | 0.0460 (7) | −0.0019 (5) | 0.0137 (5) | 0.0019 (5) |
C11 | 0.0445 (7) | 0.0990 (13) | 0.0673 (10) | −0.0210 (8) | 0.0077 (7) | −0.0048 (9) |
N1 | 0.0399 (6) | 0.0618 (7) | 0.0579 (7) | −0.0126 (5) | 0.0124 (5) | −0.0070 (5) |
O1 | 0.0464 (6) | 0.0917 (8) | 0.0675 (7) | −0.0275 (5) | 0.0098 (5) | −0.0114 (6) |
O2 | 0.0465 (5) | 0.0848 (7) | 0.0525 (6) | −0.0161 (5) | 0.0072 (4) | −0.0123 (5) |
C1—N1 | 1.2833 (17) | C6—C7 | 1.3997 (19) |
C1—C6 | 1.4724 (18) | C7—C8 | 1.3703 (19) |
C1—C2 | 1.498 (2) | C7—H7 | 0.9300 |
C2—C3 | 1.516 (2) | C8—C9 | 1.3907 (19) |
C2—H2A | 0.9700 | C8—H8 | 0.9300 |
C2—H2B | 0.9700 | C9—O2 | 1.3681 (16) |
C3—C4 | 1.509 (2) | C9—C10 | 1.3808 (19) |
C3—H3A | 0.9700 | C10—H10 | 0.9300 |
C3—H3B | 0.9700 | C11—O2 | 1.415 (2) |
C4—C5 | 1.5032 (19) | C11—H11A | 0.9600 |
C4—H4A | 0.9700 | C11—H11B | 0.9600 |
C4—H4B | 0.9700 | C11—H11C | 0.9600 |
C5—C10 | 1.3930 (19) | N1—O1 | 1.4164 (16) |
C5—C6 | 1.3940 (18) | O1—H1 | 0.8200 |
N1—C1—C6 | 116.90 (12) | C5—C6—C7 | 118.39 (11) |
N1—C1—C2 | 123.19 (12) | C5—C6—C1 | 119.81 (12) |
C6—C1—C2 | 119.86 (11) | C7—C6—C1 | 121.79 (11) |
C1—C2—C3 | 112.97 (11) | C8—C7—C6 | 121.59 (12) |
C1—C2—H2A | 109.0 | C8—C7—H7 | 119.2 |
C3—C2—H2A | 109.0 | C6—C7—H7 | 119.2 |
C1—C2—H2B | 109.0 | C7—C8—C9 | 119.60 (13) |
C3—C2—H2B | 109.0 | C7—C8—H8 | 120.2 |
H2A—C2—H2B | 107.8 | C9—C8—H8 | 120.2 |
C4—C3—C2 | 111.67 (13) | O2—C9—C10 | 124.44 (11) |
C4—C3—H3A | 109.3 | O2—C9—C8 | 115.63 (12) |
C2—C3—H3A | 109.3 | C10—C9—C8 | 119.93 (12) |
C4—C3—H3B | 109.3 | C9—C10—C5 | 120.47 (11) |
C2—C3—H3B | 109.3 | C9—C10—H10 | 119.8 |
H3A—C3—H3B | 107.9 | C5—C10—H10 | 119.8 |
C5—C4—C3 | 110.81 (12) | O2—C11—H11A | 109.5 |
C5—C4—H4A | 109.5 | O2—C11—H11B | 109.5 |
C3—C4—H4A | 109.5 | H11A—C11—H11B | 109.5 |
C5—C4—H4B | 109.5 | O2—C11—H11C | 109.5 |
C3—C4—H4B | 109.5 | H11A—C11—H11C | 109.5 |
H4A—C4—H4B | 108.1 | H11B—C11—H11C | 109.5 |
C10—C5—C6 | 120.00 (12) | C1—N1—O1 | 112.30 (12) |
C10—C5—C4 | 120.37 (11) | N1—O1—H1 | 109.5 |
C6—C5—C4 | 119.62 (11) | C9—O2—C11 | 118.02 (12) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1i | 0.82 | 2.09 | 2.805 (2) | 146 |
Symmetry code: (i) −x, −y, −z+2. |
Experimental details
Crystal data | |
Chemical formula | C11H13NO2 |
Mr | 191.22 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 290 |
a, b, c (Å) | 8.185 (6), 15.878 (10), 8.053 (5) |
β (°) | 109.02 (3) |
V (Å3) | 989.4 (11) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.12 × 0.11 × 0.09 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID diffractometer |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.989, 0.992 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9568, 2260, 1724 |
Rint | 0.024 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.045, 0.140, 1.10 |
No. of reflections | 2260 |
No. of parameters | 129 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.14, −0.20 |
Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1i | 0.82 | 2.09 | 2.805 (2) | 146.2 |
Symmetry code: (i) −x, −y, −z+2. |
As a part of our study of 2,3,4,5-tetrahydro-7-methoxy-1H-2-benzazepin-1-one and its isomer, which exhibit anticonvulsant activities (Wei et al., 2009), we report here the crystal structure of the title compound, which was used in our attempts to improve the selectivity of Backmann rearrangement.
In the title compound (Fig. 1) all bond lengths and angles are normal. Intermolecular O—H···N hydrogen bonds (Table 1) link molecules into centrosymmetric dimer. The cystal packing is further stablized by van der Waals forces.