supplementary materials


fj2480 scheme

Acta Cryst. (2012). E68, o174    [ doi:10.1107/S1600536811053657 ]

(2-Aminophenyl)methanol

C. F. Zipp, M. A. Fernandes, H. M. Marques and J. P. Michael

Abstract top

The crystal strucure of the title compound, C7H9NO, displays N-H...O hydrogen bonds which link molecules related by translation along the b axis, and O-H...N and further N-H...O hydrogen bonds which link molecules related by the 21 screw axis along the c axis. The resulting combination is a hydrogen-bonded layer of molecules parallel to (011).

Comment top

Amines play an important role in various areas of chemistry. Amines are used as precursors to amide and peptide functional groups in organic chemistry. The acid-base properties of amines are important in the synthesis of salts. These properties, as well as their hydrogen bonding capabilities, make amines an important functionality in the pharmaceutical industry (Morissette et al., 2004). The hydrogen bonding capabilities of amines also make them an important component of the crystal engineer's arsenal (Bernstein et al., 1999).

The title compound (I) is capable of forming hydrogen bonds through the alcohol and amine groups (Fig. 1). In this structure, molecules related by translation along the b axis are linked by the N1—H1A···O1 hydrogen bond to form a C6 chain (Etter et al., 1990; Bernstein et al., 1995) along the b axis. In addition, molecules related by the 2 fold screw axis along c, are held together by the O1—H1···N1 hydrogen bond and the N1—H1B···O1 to form a chain of molecules which appear as a stack of molecules when viewed down the c axis (Fig. 2). The combination of these two hydrogen bonded chains results in a hydrogen bonded layer of molecules parallel to (011).

Related literature top

For the use of amines in the pharmaceutical industry, see: Morissette et al. (2004). For the use of amines in crystal engineering, see: Bernstein et al. (1999). For hydrogen-bond motifs, see: Bernstein et al. (1995); Etter et al. (1990).

Experimental top

The title compound was purchased from Sigma Aldrich and was recrystallized from dichloromethane and hexane (1:1) to yield colourless needles.

Refinement top

With the exception of those involved in hydrogen bonding, all H atoms were first located in the difference Fourier map and then positioned geometrically, and allowed to ride on their parent atoms. Hydrogen bond lengths were set as follows for C—H = 0.95 Å (CH) or 0.99 Å (CH2). Hydrogen atoms involved in hydrogen bonding (N—H and O—H) were located in the difference Fourier map and then allowed to ride on their parent atoms with unmodified N—H and O—H distances. Isotropic displacement parameters for the H atoms were set as follows: 1.2 times Ueq of the parent atom for C and N, and 1.5 times Ueq of the parent atom for O. Though the molecule crystallizes in a polar space group it was not possible to determine the absolute conformation of the crystal. As a consequence all Friedel pairs were merged during the final refinements with a SHELXL97 MERG 4 instruction.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and SCHAKAL99 (Keller, 1999); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. Diagram showing the intermolecular N—H···O and O—H···N hydrogen bonding network in the structure of (I). Molecules related by translation along the b axis are held together by the N1—H1A···O1 hydrogen bond. In addition, molecules related by the 2 fold screw axis along c are held together by the O1—H1···N1 and N1—H1B···O1 hydrogen bonds which appear as a stack of molecules when viewed down the c axis.
(2-Aminophenyl)methanol top
Crystal data top
C7H9NOF(000) = 264
Mr = 123.15Dx = 1.268 Mg m3
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 3105 reflections
a = 22.6222 (9) Åθ = 3.5–28.3°
b = 6.0675 (2) ŵ = 0.09 mm1
c = 4.7005 (2) ÅT = 173 K
V = 645.19 (4) Å3Needle, colourless
Z = 40.46 × 0.20 × 0.07 mm
Data collection top
Bruker APEXII CCD
diffractometer
681 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.078
graphiteθmax = 26.0°, θmin = 1.8°
φ and ω scansh = 2727
4682 measured reflectionsk = 76
715 independent reflectionsl = 55
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)] = 0.030Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.075H-atom parameters constrained
S = 1.09 w = 1/[σ2(Fo2) + (0.0244P)2 + 0.1192P]
where P = (Fo2 + 2Fc2)/3
715 reflections(Δ/σ)max < 0.001
82 parametersΔρmax = 0.12 e Å3
1 restraintΔρmin = 0.13 e Å3
Crystal data top
C7H9NOV = 645.19 (4) Å3
Mr = 123.15Z = 4
Orthorhombic, Pna21Mo Kα radiation
a = 22.6222 (9) ŵ = 0.09 mm1
b = 6.0675 (2) ÅT = 173 K
c = 4.7005 (2) Å0.46 × 0.20 × 0.07 mm
Data collection top
Bruker APEXII CCD
diffractometer
681 reflections with I > 2σ(I)
4682 measured reflectionsRint = 0.078
715 independent reflectionsθmax = 26.0°
Refinement top
R[F2 > 2σ(F2)] = 0.030H-atom parameters constrained
wR(F2) = 0.075Δρmax = 0.12 e Å3
S = 1.09Δρmin = 0.13 e Å3
715 reflectionsAbsolute structure: ?
82 parametersFlack parameter: ?
1 restraintRogers parameter: ?
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.38086 (8)0.4709 (3)0.5647 (4)0.0316 (4)
C20.40551 (8)0.2625 (3)0.6243 (5)0.0306 (4)
C30.37720 (9)0.1240 (3)0.8170 (5)0.0378 (5)
H30.39380.01610.85830.045*
C40.32549 (9)0.1866 (3)0.9489 (6)0.0443 (5)
H40.30670.08891.07830.053*
C50.30074 (9)0.3917 (4)0.8937 (6)0.0450 (5)
H50.26530.43640.98550.054*
C60.32908 (9)0.5302 (3)0.7009 (5)0.0383 (5)
H60.31220.67040.66150.046*
C70.40968 (8)0.6224 (3)0.3546 (5)0.0348 (5)
H7A0.41510.54450.17140.042*
H7B0.38390.75150.32070.042*
N10.45972 (7)0.1975 (2)0.5061 (4)0.0343 (4)
H1A0.46370.05570.49040.041*
H1B0.47350.26440.34500.041*
O10.46612 (5)0.69530 (18)0.4600 (3)0.0350 (4)
H10.48720.71760.31230.053*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0345 (9)0.0258 (8)0.0344 (10)0.0039 (7)0.0059 (9)0.0007 (8)
C20.0357 (9)0.0243 (8)0.0319 (9)0.0036 (7)0.0055 (10)0.0008 (8)
C30.0440 (11)0.0279 (9)0.0415 (12)0.0051 (8)0.0051 (10)0.0048 (10)
C40.0448 (11)0.0428 (11)0.0451 (12)0.0116 (9)0.0010 (11)0.0089 (11)
C50.0360 (11)0.0488 (12)0.0501 (13)0.0034 (9)0.0034 (11)0.0022 (10)
C60.0356 (10)0.0335 (10)0.0458 (13)0.0011 (8)0.0041 (10)0.0021 (9)
C70.0386 (10)0.0281 (9)0.0377 (11)0.0005 (8)0.0042 (9)0.0035 (9)
N10.0424 (9)0.0216 (7)0.0387 (10)0.0011 (6)0.0016 (8)0.0001 (7)
O10.0387 (7)0.0284 (6)0.0380 (8)0.0055 (5)0.0009 (7)0.0009 (6)
Geometric parameters (Å, °) top
C1—C61.383 (3)C5—C61.393 (3)
C1—C21.410 (2)C5—H50.9500
C1—C71.498 (3)C6—H60.9500
C2—C31.392 (3)C7—O11.439 (2)
C2—N11.403 (2)C7—H7A0.9900
C3—C41.377 (3)C7—H7B0.9900
C3—H30.9500N1—H1A0.8683
C4—C51.389 (3)N1—H1B0.9141
C4—H40.9500O1—H10.8534
C6—C1—C2118.46 (17)C6—C5—H5120.8
C6—C1—C7120.94 (16)C1—C6—C5122.29 (18)
C2—C1—C7120.59 (17)C1—C6—H6118.9
C3—C2—N1119.38 (16)C5—C6—H6118.9
C3—C2—C1119.25 (18)O1—C7—C1110.35 (17)
N1—C2—C1121.26 (16)O1—C7—H7A109.6
C4—C3—C2121.18 (18)C1—C7—H7A109.6
C4—C3—H3119.4O1—C7—H7B109.6
C2—C3—H3119.4C1—C7—H7B109.6
C3—C4—C5120.3 (2)H7A—C7—H7B108.1
C3—C4—H4119.8C2—N1—H1A113.8
C5—C4—H4119.8C2—N1—H1B120.1
C4—C5—C6118.5 (2)H1A—N1—H1B109.5
C4—C5—H5120.8C7—O1—H1105.4
C6—C1—C2—C30.1 (3)C3—C4—C5—C60.6 (3)
C7—C1—C2—C3178.96 (19)C2—C1—C6—C50.1 (3)
C6—C1—C2—N1176.24 (17)C7—C1—C6—C5179.0 (2)
C7—C1—C2—N14.9 (3)C4—C5—C6—C10.3 (3)
N1—C2—C3—C4176.60 (19)C6—C1—C7—O1114.52 (18)
C1—C2—C3—C40.4 (3)C2—C1—C7—O166.6 (2)
C2—C3—C4—C50.7 (3)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N1i0.851.942.791 (2)172
N1—H1B···O1i0.912.283.135 (2)156
N1—H1A···O1ii0.872.193.0585 (17)175
Symmetry codes: (i) −x+1, −y+1, z−1/2; (ii) x, y−1, z.
Table 1
Hydrogen-bond geometry (Å, °)
top
D—H···AD—HH···AD···AD—H···A
O1—H1···N1i0.851.942.791 (2)172
N1—H1B···O1i0.912.283.135 (2)156
N1—H1A···O1ii0.872.193.0585 (17)175
Symmetry codes: (i) −x+1, −y+1, z−1/2; (ii) x, y−1, z.
Acknowledgements top

This work was supported by the National Research Foundation, Pretoria (NRF, GUN 2053652 & 77122), the South African Research Chairs Initiative and the University of the Witwatersrand.

references
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