organic compounds
(2-Aminophenyl)methanol
aMolecular Sciences Institute, School of Chemistry, University of the Witwatersrand, PO Wits 2050, Johannesburg, South Africa
*Correspondence e-mail: manuel.fernandes@wits.ac.za
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).
Related literature
For the use of et al. (2004). For the use of in crystal engineering, see: Bernstein et al. (1999). For hydrogen-bond motifs, see: Bernstein et al. (1995); Etter et al. (1990).
in the pharmaceutical industry, see: MorissetteExperimental
Crystal data
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Data collection
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Refinement
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Data collection: APEX2 (Bruker, 2005); cell SAINT (Bruker, 2005); data reduction: SAINT; 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).
Supporting information
10.1107/S1600536811053657/fj2480sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536811053657/fj2480Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536811053657/fj2480Isup3.cml
The title compound was purchased from Sigma Aldrich and was recrystallized from dichloromethane and hexane (1:1) to yield colourless needles.
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
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.Data collection: APEX2 (Bruker, 2005); cell
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).C7H9NO | F(000) = 264 |
Mr = 123.15 | Dx = 1.268 Mg m−3 |
Orthorhombic, Pna21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2n | Cell parameters from 3105 reflections |
a = 22.6222 (9) Å | θ = 3.5–28.3° |
b = 6.0675 (2) Å | µ = 0.09 mm−1 |
c = 4.7005 (2) Å | T = 173 K |
V = 645.19 (4) Å3 | Needle, colourless |
Z = 4 | 0.46 × 0.20 × 0.07 mm |
Bruker APEXII CCD diffractometer | 681 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.078 |
Graphite monochromator | θmax = 26.0°, θmin = 1.8° |
ϕ and ω scans | h = −27→27 |
4682 measured reflections | k = −7→6 |
715 independent reflections | l = −5→5 |
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)] = 0.030 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.075 | H-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 parameters | Δρmax = 0.12 e Å−3 |
1 restraint | Δρmin = −0.13 e Å−3 |
C7H9NO | V = 645.19 (4) Å3 |
Mr = 123.15 | Z = 4 |
Orthorhombic, Pna21 | Mo Kα radiation |
a = 22.6222 (9) Å | µ = 0.09 mm−1 |
b = 6.0675 (2) Å | T = 173 K |
c = 4.7005 (2) Å | 0.46 × 0.20 × 0.07 mm |
Bruker APEXII CCD diffractometer | 681 reflections with I > 2σ(I) |
4682 measured reflections | Rint = 0.078 |
715 independent reflections |
R[F2 > 2σ(F2)] = 0.030 | 1 restraint |
wR(F2) = 0.075 | H-atom parameters constrained |
S = 1.09 | Δρmax = 0.12 e Å−3 |
715 reflections | Δρmin = −0.13 e Å−3 |
82 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 | 0.38086 (8) | 0.4709 (3) | 0.5647 (4) | 0.0316 (4) | |
C2 | 0.40551 (8) | 0.2625 (3) | 0.6243 (5) | 0.0306 (4) | |
C3 | 0.37720 (9) | 0.1240 (3) | 0.8170 (5) | 0.0378 (5) | |
H3 | 0.3938 | −0.0161 | 0.8583 | 0.045* | |
C4 | 0.32549 (9) | 0.1866 (3) | 0.9489 (6) | 0.0443 (5) | |
H4 | 0.3067 | 0.0889 | 1.0783 | 0.053* | |
C5 | 0.30074 (9) | 0.3917 (4) | 0.8937 (6) | 0.0450 (5) | |
H5 | 0.2653 | 0.4364 | 0.9855 | 0.054* | |
C6 | 0.32908 (9) | 0.5302 (3) | 0.7009 (5) | 0.0383 (5) | |
H6 | 0.3122 | 0.6704 | 0.6615 | 0.046* | |
C7 | 0.40968 (8) | 0.6224 (3) | 0.3546 (5) | 0.0348 (5) | |
H7A | 0.4151 | 0.5445 | 0.1714 | 0.042* | |
H7B | 0.3839 | 0.7515 | 0.3207 | 0.042* | |
N1 | 0.45972 (7) | 0.1975 (2) | 0.5061 (4) | 0.0343 (4) | |
H1A | 0.4637 | 0.0557 | 0.4904 | 0.041* | |
H1B | 0.4735 | 0.2644 | 0.3450 | 0.041* | |
O1 | 0.46612 (5) | 0.69530 (18) | 0.4600 (3) | 0.0350 (4) | |
H1 | 0.4872 | 0.7176 | 0.3123 | 0.053* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0345 (9) | 0.0258 (8) | 0.0344 (10) | −0.0039 (7) | −0.0059 (9) | 0.0007 (8) |
C2 | 0.0357 (9) | 0.0243 (8) | 0.0319 (9) | −0.0036 (7) | −0.0055 (10) | −0.0008 (8) |
C3 | 0.0440 (11) | 0.0279 (9) | 0.0415 (12) | −0.0051 (8) | −0.0051 (10) | 0.0048 (10) |
C4 | 0.0448 (11) | 0.0428 (11) | 0.0451 (12) | −0.0116 (9) | 0.0010 (11) | 0.0089 (11) |
C5 | 0.0360 (11) | 0.0488 (12) | 0.0501 (13) | −0.0034 (9) | 0.0034 (11) | 0.0022 (10) |
C6 | 0.0356 (10) | 0.0335 (10) | 0.0458 (13) | 0.0011 (8) | −0.0041 (10) | 0.0021 (9) |
C7 | 0.0386 (10) | 0.0281 (9) | 0.0377 (11) | −0.0005 (8) | −0.0042 (9) | 0.0035 (9) |
N1 | 0.0424 (9) | 0.0216 (7) | 0.0387 (10) | 0.0011 (6) | 0.0016 (8) | 0.0001 (7) |
O1 | 0.0387 (7) | 0.0284 (6) | 0.0380 (8) | −0.0055 (5) | 0.0009 (7) | 0.0009 (6) |
C1—C6 | 1.383 (3) | C5—C6 | 1.393 (3) |
C1—C2 | 1.410 (2) | C5—H5 | 0.9500 |
C1—C7 | 1.498 (3) | C6—H6 | 0.9500 |
C2—C3 | 1.392 (3) | C7—O1 | 1.439 (2) |
C2—N1 | 1.403 (2) | C7—H7A | 0.9900 |
C3—C4 | 1.377 (3) | C7—H7B | 0.9900 |
C3—H3 | 0.9500 | N1—H1A | 0.8683 |
C4—C5 | 1.389 (3) | N1—H1B | 0.9141 |
C4—H4 | 0.9500 | O1—H1 | 0.8534 |
C6—C1—C2 | 118.46 (17) | C6—C5—H5 | 120.8 |
C6—C1—C7 | 120.94 (16) | C1—C6—C5 | 122.29 (18) |
C2—C1—C7 | 120.59 (17) | C1—C6—H6 | 118.9 |
C3—C2—N1 | 119.38 (16) | C5—C6—H6 | 118.9 |
C3—C2—C1 | 119.25 (18) | O1—C7—C1 | 110.35 (17) |
N1—C2—C1 | 121.26 (16) | O1—C7—H7A | 109.6 |
C4—C3—C2 | 121.18 (18) | C1—C7—H7A | 109.6 |
C4—C3—H3 | 119.4 | O1—C7—H7B | 109.6 |
C2—C3—H3 | 119.4 | C1—C7—H7B | 109.6 |
C3—C4—C5 | 120.3 (2) | H7A—C7—H7B | 108.1 |
C3—C4—H4 | 119.8 | C2—N1—H1A | 113.8 |
C5—C4—H4 | 119.8 | C2—N1—H1B | 120.1 |
C4—C5—C6 | 118.5 (2) | H1A—N1—H1B | 109.5 |
C4—C5—H5 | 120.8 | C7—O1—H1 | 105.4 |
C6—C1—C2—C3 | −0.1 (3) | C3—C4—C5—C6 | 0.6 (3) |
C7—C1—C2—C3 | −178.96 (19) | C2—C1—C6—C5 | 0.1 (3) |
C6—C1—C2—N1 | −176.24 (17) | C7—C1—C6—C5 | 179.0 (2) |
C7—C1—C2—N1 | 4.9 (3) | C4—C5—C6—C1 | −0.3 (3) |
N1—C2—C3—C4 | 176.60 (19) | C6—C1—C7—O1 | 114.52 (18) |
C1—C2—C3—C4 | 0.4 (3) | C2—C1—C7—O1 | −66.6 (2) |
C2—C3—C4—C5 | −0.7 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1i | 0.85 | 1.94 | 2.791 (2) | 172 |
N1—H1B···O1i | 0.91 | 2.28 | 3.135 (2) | 156 |
N1—H1A···O1ii | 0.87 | 2.19 | 3.0585 (17) | 175 |
Symmetry codes: (i) −x+1, −y+1, z−1/2; (ii) x, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | C7H9NO |
Mr | 123.15 |
Crystal system, space group | Orthorhombic, Pna21 |
Temperature (K) | 173 |
a, b, c (Å) | 22.6222 (9), 6.0675 (2), 4.7005 (2) |
V (Å3) | 645.19 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.46 × 0.20 × 0.07 |
Data collection | |
Diffractometer | Bruker APEXII CCD diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4682, 715, 681 |
Rint | 0.078 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.030, 0.075, 1.09 |
No. of reflections | 715 |
No. of parameters | 82 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.12, −0.13 |
Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and SCHAKAL99 (Keller, 1999), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1i | 0.85 | 1.94 | 2.791 (2) | 172 |
N1—H1B···O1i | 0.91 | 2.28 | 3.135 (2) | 156 |
N1—H1A···O1ii | 0.87 | 2.19 | 3.0585 (17) | 175 |
Symmetry codes: (i) −x+1, −y+1, z−1/2; (ii) x, y−1, z. |
Acknowledgements
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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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).