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The title compound, C11H11NO3, has two mol­ecules in the asymmetric unit, which differ in the orientation of their side-chain OH groups, allowing them to form inter­molecular O—H...O hydrogen bonds to different acceptors. In one case, the acceptor is the OH group of the other mol­ecule, and in the other case it is an imide O=C group. This is the first example in the N-substituted phthalimide series in which independent mol­ecules have different types of acceptor. Mol­ecular-orbital calculations place the greatest negative charge on the OH group.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270108016363/hj3075sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270108016363/hj3075Isup2.hkl
Contains datablock I

CCDC reference: 697589

Comment top

N-substituted phthalimides, (I), are of interest for biological activity in their own right (Lima et al., 2002) and as precursors for synthesis (Couture et al., 1998). Crystallographic studies have appeared recently in which the imide N atom bears a nonpolar substituent such as ethyl, (Ia) (Liang & Li, 2006c), or allyl, (Ib) (Warzecha et al., 2006). Other studies have investigated the situation when an N-alkyl substituent terminates with a hydrogen-bond donor, including hydroxymethyl, (Ic) (Liang & Li, 2006a), hydroxyethyl, (Id) (Liang & Li, 2006b), and a series of alkanoic acids, (Ie)–(Ii) (Feeder & Jones, 1996). The title compound, (Ij), corresponds to (If) with its carboxyl CO group replaced by CH2.

The two independent molecules of (Ij) are illustrated in Fig. 1. Their isoindoline ring systems are planar, with r.m.s. deviations of 0.01 Å, and the angle between these ring planes is only 1.65 (8)°. The bond distances and angles have values similar to those in related compounds. While the short-chain members of the series, (Ia)–(If), have Z' = 1, two of the longer-chain compounds, (Ig) and (Ii), have Z' = 2, the independent molecules differing in their conformation. As in (Ib) and (If)–(Ii), the alkyl chains of (Ij) lie out of the ring planes.

In the series of molecules (Ic)–(Ij), there is a single strong hydrogen-bond donor, the OH group of the hydroxyl or carboxyl group. A variety of O atoms compete to accept the hydrogen bond, viz. the OH group itself, the carboxyl OC group if present and the two imide O atoms, which are aided by electron donation from the imide N atom. In both (Ic) and (Id), one of the imide O atoms is the acceptor. Such an O atom is even able to capture a hydrogen bond from the carboxyl group in (Ie) and (If), although the other members of this series, (Ig)–(Ii), form the familiar carboxyl dimers (Feeder & Jones, 1996).

In (Ij), the hydrogen bonding is more complex. Torsion angles along the independent hydroxyalkyl chains of (Ij) (Table 1) start with fairly typical values, but a drastic change at the end affects the orientation of the terminal OH groups. Fig. 2 shows a superposition made with Mercury (Macrae et al., 2006) of atoms C1 and C21, N2 and N22, C3 and C23, which gives an r.m.s. deviation 0.007 Å. This superposition leaves a distance of 0.680 Å between atoms O11 and O31, 1.017 Å between H11 and H31, and only 0.210 Å between H31 and O11. Alternative locations for H11 and H31 can be discounted in view of their successful rotating-group refinement and the small size of the maximum difference electron density, just 0.148 e Å-3. Both OH groups donate hydrogen bonds (Fig. 3 and Table 2), but for O11/H11 the acceptor is imide atom O32, while for O31/H31 it is the hydroxyl atom O11 of the other independent molecule. C(10) chains (Bernstein et al., 1995) (highlighted in Fig. 3) are thereby created. Both hydrogen bonds show excellent linearity (O—H···O > 170°) and nearly identical distances. Unable to accept an O—H···O hydrogen bond, atom O31 accepts a reasonably strong C—H···O hydrogen bond. Other weak C—H···O interactions with H···O greater than 2.50 Å involving H25, H26 and H27 are not shown, but may make a small contribution to the stability of the crystal structure.

A derivative of (Ij) with complete 4,5,7-trichloro-6-(2,4-dimethylthiazol-5-yl) substitution on the phenyl ring (Fun et al., 2007) has successive torsion angles along the alkyl chain that are similar in magnitude within 18° to those for the C8–C10/O11 unit of (Ij), but C8—C9—C10—O11 is opposite in sign. The hydrogen bonding is entirely different, a thiazole N atom acting as acceptor for the OH group. The similar structure (If) is constructed from just one type of independent molecule and has a stronger intermolecular O—H···O hydrogen bond to an imide O atom, forming chains; its H···O and O···O distances are 1.82 and 2.689 Å (Feeder & Jones, 1996). Its carboxyl O(=C) atom only accepts C—H···O hydrogen bonds, and C—H···O hydrogen bonds link the chains into sheets.

To provide some insight into hydrogen-bond acceptor strength, Löwdin charges were calculated for the O atoms of (Ij) after optimization of geometry with GAMESS (Schmidt et al., 1993) in the 6–31G* basis set. The charge of -0.519 on the hydroxy O atom is considerably greater than those of -0.311 and -0.308 on the imide O atoms, suggesting that the former should be a more attractive hydrogen-bond acceptor. Taken together, the molecular orbital results for (Ij) and crystallographic results for (Ic), (Id) and (Ij) suggest that once the linkage between the phthalimide ring and the hydroxyl group becomes sufficiently long and flexible to position it properly, the latter group can assert its acceptor strength and receive an O—H···O or C—H···O hydrogen bond.

Related literature top

For related literature, see: Bernstein et al. (1995); Couture et al. (1998); Feeder & Jones (1996); Fun et al. (2007); Liang & Li (2006a, 2006b, 2006c); Lima et al. (2002); Macrae et al. (2006); Schmidt et al. (1993); Warzecha et al. (2006).

Experimental top

Crystals suitable for X-ray diffraction were obtained by slow evaporation of a solution in dichloromethane/hexane (8:1).

Refinement top

H atoms attached to C atom were positioned geometrically at C—H distances 0.93 or 0.97 Å and refined using a riding model with Uiso(H) values of 1.2Ueq(C). H atoms in the OH groups were refined as rotating groups with an O—H distance of 0.82 Å and Uiso(H) values of 1.5Ueq(O).

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: CADABS (Gould & Smith, 1986); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure and the atom-numbering scheme for (Ij). Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. Superposition with Mercury (Macrae et al., 2006) of the phthalimide N atoms and the carbonyl C atoms in the two independent molecules of (Ij).
[Figure 3] Fig. 3. The unit-cell contents of (Ij). Heteroatoms are shown as ellipsoids, C atoms as spheres; H atoms have been omitted except for those involved in hydrogen bonds, which are shown as dashed lines. The C(10) motif is traced in solid lines. Other covalent bonds are shown as open bonds.
2-(3-Hydroxypropyl)isoindoline-1,3-dione top
Crystal data top
C11H11NO3F(000) = 864
Mr = 205.21Dx = 1.363 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 25 reflections
a = 12.2439 (17) Åθ = 8.0–12.1°
b = 7.4543 (8) ŵ = 0.10 mm1
c = 21.973 (2) ÅT = 294 K
β = 94.282 (10)°Block, colourless
V = 1999.9 (4) Å30.43 × 0.42 × 0.40 mm
Z = 8
Data collection top
Enraf–Nonius CAD-4
diffractometer
Rint = 0.052
Radiation source: fine-focus sealed tubeθmax = 25.3°, θmin = 2.4°
Graphite monochromatorh = 1414
w/2θ scansk = 82
4424 measured reflectionsl = 260
3583 independent reflections3 standard reflections every 120 min
1805 reflections with I > 2σ(I) intensity decay: 6%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124H-atom parameters constrained
S = 0.97 w = 1/[σ2(Fo2) + (0.0531P)2 + 0.2706P]
where P = (Fo2 + 2Fc2)/3
3583 reflections(Δ/σ)max < 0.001
273 parametersΔρmax = 0.15 e Å3
0 restraintsΔρmin = 0.17 e Å3
Crystal data top
C11H11NO3V = 1999.9 (4) Å3
Mr = 205.21Z = 8
Monoclinic, P21/cMo Kα radiation
a = 12.2439 (17) ŵ = 0.10 mm1
b = 7.4543 (8) ÅT = 294 K
c = 21.973 (2) Å0.43 × 0.42 × 0.40 mm
β = 94.282 (10)°
Data collection top
Enraf–Nonius CAD-4
diffractometer
Rint = 0.052
4424 measured reflections3 standard reflections every 120 min
3583 independent reflections intensity decay: 6%
1805 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0430 restraints
wR(F2) = 0.124H-atom parameters constrained
S = 0.97Δρmax = 0.15 e Å3
3583 reflectionsΔρmin = 0.17 e Å3
273 parameters
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.0857 (2)1.0403 (4)0.18923 (12)0.0501 (7)
N20.03687 (16)1.0749 (3)0.13558 (10)0.0515 (6)
C30.1115 (2)1.1357 (4)0.09001 (13)0.0530 (7)
C3A0.2188 (2)1.1443 (3)0.11742 (12)0.0473 (7)
C40.3210 (2)1.1925 (4)0.09265 (14)0.0620 (8)
H40.33181.22920.05220.074*
C50.4064 (2)1.1847 (4)0.12939 (17)0.0717 (9)
H50.47641.21550.11340.086*
C60.3910 (2)1.1324 (5)0.18949 (17)0.0735 (10)
H60.45031.13090.21360.088*
C70.2885 (2)1.0822 (4)0.21461 (13)0.0631 (8)
H70.27791.04510.25500.076*
C7A0.2027 (2)1.0891 (4)0.17735 (11)0.0476 (7)
C80.0787 (2)1.0381 (4)0.12831 (14)0.0603 (8)
H8A0.08871.01800.08550.072*
H8B0.09990.92930.15030.072*
C90.1525 (2)1.1912 (4)0.15169 (13)0.0575 (8)
H9A0.13671.29650.12660.069*
H9B0.13641.22020.19310.069*
C100.2723 (2)1.1459 (4)0.15085 (13)0.0622 (8)
H10A0.28931.12390.10910.075*
H10B0.31551.24780.16600.075*
O110.30206 (16)0.9926 (3)0.18694 (9)0.0680 (6)
H110.32011.02410.22200.102*
O120.03913 (15)0.9773 (3)0.23486 (9)0.0700 (6)
O130.09064 (17)1.1723 (3)0.03867 (9)0.0769 (6)
C210.6527 (2)0.6600 (4)0.14759 (12)0.0454 (6)
N220.58970 (15)0.7259 (3)0.09773 (9)0.0457 (5)
C230.6517 (2)0.7526 (4)0.04758 (12)0.0479 (7)
C23A0.76489 (19)0.6991 (3)0.06836 (11)0.0434 (6)
C240.8595 (2)0.7014 (4)0.03807 (12)0.0545 (7)
H240.85930.73850.00240.065*
C250.9551 (2)0.6459 (4)0.07051 (13)0.0609 (8)
H251.02050.64700.05150.073*
C260.9555 (2)0.5897 (4)0.12984 (13)0.0564 (8)
H261.02110.55330.15020.068*
C270.8603 (2)0.5859 (4)0.16019 (12)0.0501 (7)
H270.86040.54700.20040.060*
C27A0.76569 (18)0.6419 (3)0.12834 (11)0.0409 (6)
C280.47280 (19)0.7655 (4)0.09744 (12)0.0506 (7)
H28A0.45590.86810.07130.061*
H28B0.45550.79710.13840.061*
C290.4024 (2)0.6092 (4)0.07535 (13)0.0571 (7)
H29A0.42220.50470.10010.068*
H29B0.41690.58170.03360.068*
C300.2817 (2)0.6459 (5)0.07820 (13)0.0626 (8)
H30A0.26440.76060.05900.075*
H30B0.24030.55430.05520.075*
O310.24918 (17)0.6489 (3)0.13834 (9)0.0682 (6)
H310.26830.74380.15470.102*
O320.61797 (14)0.6272 (3)0.19668 (8)0.0591 (5)
O330.61543 (15)0.8093 (3)0.00116 (8)0.0668 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0541 (16)0.0475 (17)0.0478 (16)0.0066 (14)0.0020 (13)0.0021 (14)
N20.0443 (12)0.0569 (15)0.0540 (14)0.0033 (11)0.0068 (11)0.0009 (12)
C30.0578 (17)0.0473 (18)0.0542 (17)0.0028 (14)0.0062 (13)0.0030 (14)
C3A0.0502 (16)0.0362 (16)0.0553 (16)0.0014 (13)0.0021 (12)0.0052 (14)
C40.0611 (18)0.0515 (19)0.0718 (19)0.0090 (15)0.0059 (15)0.0052 (16)
C50.0521 (18)0.058 (2)0.104 (3)0.0035 (16)0.0008 (18)0.008 (2)
C60.0517 (18)0.074 (2)0.098 (3)0.0048 (17)0.0234 (17)0.022 (2)
C70.0636 (18)0.069 (2)0.0584 (17)0.0113 (17)0.0138 (14)0.0109 (17)
C7A0.0520 (16)0.0428 (16)0.0480 (15)0.0056 (13)0.0031 (12)0.0078 (13)
C80.0475 (16)0.061 (2)0.0724 (19)0.0003 (15)0.0074 (14)0.0078 (16)
C90.0553 (17)0.0489 (18)0.0694 (18)0.0000 (14)0.0131 (13)0.0000 (15)
C100.0584 (18)0.064 (2)0.0659 (19)0.0061 (16)0.0126 (14)0.0015 (17)
O110.0720 (13)0.0697 (15)0.0607 (12)0.0117 (12)0.0064 (10)0.0127 (12)
O120.0674 (12)0.0833 (17)0.0570 (12)0.0044 (12)0.0098 (10)0.0074 (12)
O130.0828 (14)0.0903 (17)0.0594 (13)0.0039 (12)0.0163 (10)0.0184 (12)
C210.0470 (15)0.0421 (17)0.0470 (16)0.0019 (13)0.0027 (12)0.0048 (13)
N220.0389 (11)0.0510 (14)0.0467 (12)0.0046 (10)0.0001 (9)0.0024 (11)
C230.0537 (16)0.0469 (17)0.0430 (15)0.0019 (13)0.0030 (13)0.0045 (14)
C23A0.0427 (14)0.0415 (16)0.0456 (15)0.0028 (12)0.0013 (11)0.0056 (13)
C240.0559 (17)0.062 (2)0.0462 (15)0.0042 (15)0.0103 (13)0.0090 (14)
C250.0460 (16)0.068 (2)0.069 (2)0.0013 (15)0.0098 (14)0.0155 (17)
C260.0437 (15)0.057 (2)0.0677 (19)0.0063 (14)0.0027 (13)0.0102 (16)
C270.0506 (16)0.0458 (17)0.0531 (16)0.0020 (13)0.0012 (13)0.0044 (14)
C27A0.0394 (14)0.0391 (16)0.0439 (14)0.0005 (12)0.0016 (11)0.0038 (12)
C280.0386 (14)0.0510 (18)0.0619 (16)0.0074 (13)0.0018 (12)0.0034 (15)
C290.0476 (16)0.060 (2)0.0635 (17)0.0020 (14)0.0022 (13)0.0126 (16)
C300.0469 (16)0.079 (2)0.0617 (18)0.0073 (16)0.0019 (13)0.0145 (17)
O310.0661 (12)0.0731 (16)0.0671 (13)0.0081 (12)0.0175 (10)0.0021 (11)
O320.0562 (11)0.0716 (14)0.0507 (11)0.0025 (10)0.0109 (9)0.0094 (10)
O330.0674 (12)0.0840 (16)0.0476 (11)0.0090 (11)0.0048 (9)0.0050 (11)
Geometric parameters (Å, º) top
C1—O121.211 (3)C21—O321.214 (3)
C1—N21.385 (3)C21—N221.382 (3)
C1—C7A1.481 (4)C21—C27A1.483 (3)
N2—C31.381 (3)N22—C231.398 (3)
N2—C81.462 (3)N22—C281.461 (3)
C3—O131.206 (3)C23—O331.205 (3)
C3—C3A1.487 (4)C23—C23A1.481 (3)
C3A—C41.374 (4)C23A—C241.379 (3)
C3A—C7A1.380 (3)C23A—C27A1.384 (3)
C4—C51.369 (4)C24—C251.387 (4)
C4—H40.9300C24—H240.9300
C5—C61.376 (4)C25—C261.369 (4)
C5—H50.9300C25—H250.9300
C6—C71.385 (4)C26—C271.386 (4)
C6—H60.9300C26—H260.9300
C7—C7A1.380 (4)C27—C27A1.373 (3)
C7—H70.9300C27—H270.9300
C8—C91.521 (4)C28—C291.508 (4)
C8—H8A0.9700C28—H28A0.9700
C8—H8B0.9700C28—H28B0.9700
C9—C101.507 (4)C29—C301.508 (3)
C9—H9A0.9700C29—H29A0.9700
C9—H9B0.9700C29—H29B0.9700
C10—O111.423 (3)C30—O311.409 (3)
C10—H10A0.9700C30—H30A0.9700
C10—H10B0.9700C30—H30B0.9700
O11—H110.8200O31—H310.8200
O12—C1—N2124.8 (2)O32—C21—N22124.3 (2)
O12—C1—C7A129.1 (3)O32—C21—C27A129.2 (2)
N2—C1—C7A106.1 (2)N22—C21—C27A106.5 (2)
C3—N2—C1111.9 (2)C21—N22—C23111.8 (2)
C3—N2—C8125.2 (2)C21—N22—C28124.3 (2)
C1—N2—C8122.8 (2)C23—N22—C28123.9 (2)
O13—C3—N2125.3 (2)O33—C23—N22124.4 (2)
O13—C3—C3A128.6 (3)O33—C23—C23A130.0 (2)
N2—C3—C3A106.1 (2)N22—C23—C23A105.6 (2)
C4—C3A—C7A121.1 (3)C24—C23A—C27A121.1 (2)
C4—C3A—C3131.0 (3)C24—C23A—C23130.4 (2)
C7A—C3A—C3107.8 (2)C27A—C23A—C23108.5 (2)
C5—C4—C3A117.9 (3)C23A—C24—C25117.1 (3)
C5—C4—H4121.0C23A—C24—H24121.4
C3A—C4—H4121.0C25—C24—H24121.4
C4—C5—C6121.4 (3)C26—C25—C24121.5 (3)
C4—C5—H5119.3C26—C25—H25119.2
C6—C5—H5119.3C24—C25—H25119.2
C5—C6—C7121.0 (3)C25—C26—C27121.4 (3)
C5—C6—H6119.5C25—C26—H26119.3
C7—C6—H6119.5C27—C26—H26119.3
C7A—C7—C6117.5 (3)C27A—C27—C26117.2 (3)
C7A—C7—H7121.3C27A—C27—H27121.4
C6—C7—H7121.3C26—C27—H27121.4
C3A—C7A—C7121.1 (3)C27—C27A—C23A121.7 (2)
C3A—C7A—C1108.0 (2)C27—C27A—C21130.7 (2)
C7—C7A—C1130.9 (3)C23A—C27A—C21107.6 (2)
N2—C8—C9112.2 (2)N22—C28—C29112.4 (2)
N2—C8—H8A109.2N22—C28—H28A109.1
C9—C8—H8A109.2C29—C28—H28A109.1
N2—C8—H8B109.2N22—C28—H28B109.1
C9—C8—H8B109.2C29—C28—H28B109.1
H8A—C8—H8B107.9H28A—C28—H28B107.9
C10—C9—C8112.5 (2)C28—C29—C30112.6 (2)
C10—C9—H9A109.1C28—C29—H29A109.1
C8—C9—H9A109.1C30—C29—H29A109.1
C10—C9—H9B109.1C28—C29—H29B109.1
C8—C9—H9B109.1C30—C29—H29B109.1
H9A—C9—H9B107.8H29A—C29—H29B107.8
O11—C10—C9112.5 (2)O31—C30—C29112.9 (2)
O11—C10—H10A109.1O31—C30—H30A109.0
C9—C10—H10A109.1C29—C30—H30A109.0
O11—C10—H10B109.1O31—C30—H30B109.0
C9—C10—H10B109.1C29—C30—H30B109.0
H10A—C10—H10B107.8H30A—C30—H30B107.8
C10—O11—H11109.5C30—O31—H31109.5
O12—C1—N2—C3176.1 (3)O32—C21—N22—C23179.4 (3)
C7A—C1—N2—C31.8 (3)C27A—C21—N22—C230.1 (3)
O12—C1—N2—C80.0 (4)O32—C21—N22—C280.2 (4)
C7A—C1—N2—C8177.9 (2)C27A—C21—N22—C28179.2 (2)
C1—N2—C3—O13178.5 (3)C21—N22—C23—O33179.9 (3)
C8—N2—C3—O132.6 (5)C28—N22—C23—O330.8 (4)
C1—N2—C3—C3A1.1 (3)C21—N22—C23—C23A0.4 (3)
C8—N2—C3—C3A177.0 (2)C28—N22—C23—C23A178.8 (2)
O13—C3—C3A—C40.9 (5)O33—C23—C23A—C240.9 (5)
N2—C3—C3A—C4178.8 (3)N22—C23—C23A—C24178.6 (3)
O13—C3—C3A—C7A179.8 (3)O33—C23—C23A—C27A179.8 (3)
N2—C3—C3A—C7A0.1 (3)N22—C23—C23A—C27A0.7 (3)
C7A—C3A—C4—C50.3 (4)C27A—C23A—C24—C250.7 (4)
C3—C3A—C4—C5179.0 (3)C23—C23A—C24—C25178.5 (3)
C3A—C4—C5—C60.7 (5)C23A—C24—C25—C260.6 (4)
C4—C5—C6—C71.3 (5)C24—C25—C26—C270.1 (5)
C5—C6—C7—C7A0.9 (5)C25—C26—C27—C27A0.4 (4)
C4—C3A—C7A—C70.7 (4)C26—C27—C27A—C23A0.3 (4)
C3—C3A—C7A—C7179.7 (3)C26—C27—C27A—C21177.7 (3)
C4—C3A—C7A—C1177.8 (2)C24—C23A—C27A—C270.3 (4)
C3—C3A—C7A—C11.2 (3)C23—C23A—C27A—C27179.1 (2)
C6—C7—C7A—C3A0.1 (4)C24—C23A—C27A—C21178.7 (2)
C6—C7—C7A—C1178.0 (3)C23—C23A—C27A—C210.7 (3)
O12—C1—C7A—C3A175.9 (3)O32—C21—C27A—C270.7 (5)
N2—C1—C7A—C3A1.9 (3)N22—C21—C27A—C27178.7 (3)
O12—C1—C7A—C72.4 (5)O32—C21—C27A—C23A178.9 (3)
N2—C1—C7A—C7179.8 (3)N22—C21—C27A—C23A0.5 (3)
C1—N2—C8—C985.0 (3)C21—N22—C28—C2992.8 (3)
C3—N2—C8—C999.5 (3)C23—N22—C28—C2988.1 (3)
N2—C8—C9—C10173.6 (2)N22—C28—C29—C30176.9 (2)
C8—C9—C10—O1159.0 (3)C28—C29—C30—O3171.6 (3)
C9—C10—O11—H1189C29—C30—O31—H3176
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O31—H31···O110.822.022.832 (3)173
O11—H11···O32i0.822.042.851 (3)171
C7—H7···O31ii0.932.473.269 (3)144
C25—H25···O13iii0.932.593.307 (4)134
C26—H26···O12iv0.932.583.183 (4)123
C27—H27···O12iv0.932.573.165 (3)122
Symmetry codes: (i) x+1, y+1/2, z+1/2; (ii) x, y+1/2, z+1/2; (iii) x+1, y+2, z; (iv) x+1, y1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC11H11NO3
Mr205.21
Crystal system, space groupMonoclinic, P21/c
Temperature (K)294
a, b, c (Å)12.2439 (17), 7.4543 (8), 21.973 (2)
β (°) 94.282 (10)
V3)1999.9 (4)
Z8
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.43 × 0.42 × 0.40
Data collection
DiffractometerEnraf–Nonius CAD-4
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
4424, 3583, 1805
Rint0.052
(sin θ/λ)max1)0.600
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.124, 0.97
No. of reflections3583
No. of parameters273
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.15, 0.17

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), CADABS (Gould & Smith, 1986), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPII (Johnson, 1976).

Selected torsion angles (º) top
C1—N2—C8—C985.0 (3)C21—N22—C28—C2992.8 (3)
C3—N2—C8—C999.5 (3)C23—N22—C28—C2988.1 (3)
N2—C8—C9—C10173.6 (2)N22—C28—C29—C30176.9 (2)
C8—C9—C10—O1159.0 (3)C28—C29—C30—O3171.6 (3)
C9—C10—O11—H1189C29—C30—O31—H3176
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O31—H31···O110.822.022.832 (3)173
O11—H11···O32i0.822.042.851 (3)171
C7—H7···O31ii0.932.473.269 (3)144
Symmetry codes: (i) x+1, y+1/2, z+1/2; (ii) x, y+1/2, z+1/2.
 

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