organic compounds
The title compound, 2-hydroxy-2-(4-hydroxyphenyl)-N-methylethanaminium chloride, C9H14NO2+·Cl−, has been isolated for the first time from the genus Harrisonia. Its structure is stabilized by extensive intra- and intermolecular hydrogen bonds of type O—HO, N—HO, N—HCl and C—HCl, resulting in a three-dimensional network. Additional weak π–π stacking interactions between adjacent molecules further stabilize the crystal structure.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680502180X/lh6469sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680502180X/lh6469Isup2.hkl |
CCDC reference: 282538
Computing details top
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST95 (Nardelli, 1995) and PLATON (Spek, 2003).
2-hydroxy-2-(4-hydroxyphenyl)-N-methylethanaminium chloride top
Crystal data top
C9H14NO2+·Cl− | Dx = 1.229 Mg m−3 |
Mr = 203.66 | Melting point: 508 K |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 6750 reflections |
a = 6.7480 (13) Å | θ = 1.7–25.0° |
b = 6.9559 (13) Å | µ = 0.32 mm−1 |
c = 23.450 (4) Å | T = 293 K |
V = 1100.7 (4) Å3 | Needle, colourless |
Z = 4 | 0.58 × 0.06 × 0.05 mm |
F(000) = 432 |
Data collection top
Siemens SMART CCD area-detector diffractometer | 1928 independent reflections |
Radiation source: fine-focus sealed tube | 1400 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.058 |
Detector resolution: 8.33 pixels mm-1 | θmax = 25.0°, θmin = 1.7° |
ω scans | h = −8→7 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −8→8 |
Tmin = 0.837, Tmax = 0.984 | l = −27→25 |
5679 measured reflections |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.067 | H-atom parameters constrained |
wR(F2) = 0.120 | w = 1/[σ2(Fo2) + (0.0489P)2 + 0.1384P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max < 0.001 |
1928 reflections | Δρmax = 0.30 e Å−3 |
120 parameters | Δρmin = −0.16 e Å−3 |
0 restraints | Absolute structure: Flack (1983), with 764 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.07 (14) |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.78718 (16) | 0.32462 (17) | 0.19117 (4) | 0.0591 (3) | |
O1 | 0.5151 (5) | −0.0313 (5) | −0.09781 (10) | 0.0681 (10) | |
H1 | 0.4391 | 0.0161 | −0.1212 | 0.102* | |
O2 | 0.2186 (6) | −0.1709 (4) | 0.15505 (11) | 0.0821 (10) | |
H2 | 0.1708 | −0.2588 | 0.1362 | 0.123* | |
N1 | 0.2029 (5) | 0.1634 (5) | 0.21902 (11) | 0.0490 (8) | |
H1A | 0.0727 | 0.1882 | 0.2151 | 0.059* | |
H1B | 0.2145 | 0.0468 | 0.2354 | 0.059* | |
C1 | 0.2819 (7) | −0.0010 (5) | 0.06575 (14) | 0.0454 (10) | |
C2 | 0.1726 (7) | 0.0639 (5) | 0.02017 (16) | 0.0516 (11) | |
H2A | 0.0463 | 0.1133 | 0.0263 | 0.062* | |
C3 | 0.2482 (6) | 0.0565 (5) | −0.03480 (15) | 0.0524 (12) | |
H3 | 0.1733 | 0.1018 | −0.0653 | 0.063* | |
C4 | 0.4334 (7) | −0.0176 (5) | −0.04412 (16) | 0.0483 (11) | |
C5 | 0.5448 (7) | −0.0821 (6) | 0.00103 (15) | 0.0548 (12) | |
H5 | 0.6708 | −0.1323 | −0.0051 | 0.066* | |
C6 | 0.4680 (7) | −0.0719 (6) | 0.05558 (15) | 0.0551 (12) | |
H6 | 0.5444 | −0.1142 | 0.0861 | 0.066* | |
C7 | 0.1959 (8) | 0.0035 (6) | 0.12537 (14) | 0.0537 (11) | |
H7 | 0.0541 | 0.0329 | 0.1226 | 0.064* | |
C8 | 0.2936 (6) | 0.1550 (6) | 0.16122 (14) | 0.0496 (9) | |
H8A | 0.4338 | 0.1268 | 0.1647 | 0.060* | |
H8B | 0.2800 | 0.2791 | 0.1428 | 0.060* | |
C9 | 0.2892 (7) | 0.3078 (7) | 0.25780 (17) | 0.0741 (13) | |
H9A | 0.2224 | 0.3027 | 0.2939 | 0.111* | |
H9B | 0.2738 | 0.4336 | 0.2415 | 0.111* | |
H9C | 0.4275 | 0.2812 | 0.2632 | 0.111* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0493 (7) | 0.0812 (7) | 0.0467 (5) | −0.0056 (6) | −0.0023 (5) | 0.0021 (5) |
O1 | 0.086 (3) | 0.071 (2) | 0.0471 (15) | 0.0258 (19) | 0.0146 (17) | 0.0043 (16) |
O2 | 0.141 (3) | 0.0581 (18) | 0.0472 (15) | −0.025 (2) | 0.0002 (18) | −0.0062 (15) |
N1 | 0.0446 (19) | 0.0547 (18) | 0.0477 (16) | −0.001 (2) | −0.0013 (15) | −0.0103 (15) |
C1 | 0.051 (3) | 0.041 (2) | 0.045 (2) | −0.002 (2) | 0.000 (2) | −0.0090 (18) |
C2 | 0.049 (3) | 0.046 (2) | 0.059 (2) | 0.006 (2) | 0.002 (2) | −0.004 (2) |
C3 | 0.068 (4) | 0.045 (2) | 0.044 (2) | 0.012 (2) | −0.003 (2) | 0.0048 (18) |
C4 | 0.065 (3) | 0.037 (2) | 0.043 (2) | 0.007 (2) | 0.006 (2) | −0.0017 (19) |
C5 | 0.056 (3) | 0.049 (3) | 0.059 (3) | 0.011 (2) | 0.002 (2) | −0.002 (2) |
C6 | 0.067 (4) | 0.055 (3) | 0.043 (2) | 0.005 (3) | −0.009 (2) | −0.005 (2) |
C7 | 0.066 (3) | 0.052 (2) | 0.043 (2) | −0.010 (3) | −0.003 (2) | −0.004 (2) |
C8 | 0.047 (2) | 0.053 (2) | 0.049 (2) | −0.003 (2) | 0.0045 (19) | −0.0105 (19) |
C9 | 0.072 (3) | 0.081 (3) | 0.070 (3) | −0.018 (3) | 0.006 (2) | −0.041 (2) |
Geometric parameters (Å, º) top
O1—C4 | 1.378 (4) | C3—C4 | 1.369 (5) |
O1—H1 | 0.8200 | C3—H3 | 0.9300 |
O2—C7 | 1.407 (5) | C4—C5 | 1.374 (5) |
O2—H2 | 0.8200 | C5—C6 | 1.382 (5) |
N1—C9 | 1.475 (5) | C5—H5 | 0.9300 |
N1—C8 | 1.488 (4) | C6—H6 | 0.9300 |
N1—H1A | 0.9000 | C7—C8 | 1.501 (5) |
N1—H1B | 0.9000 | C7—H7 | 0.9800 |
C1—C6 | 1.370 (6) | C8—H8A | 0.9700 |
C1—C2 | 1.375 (5) | C8—H8B | 0.9700 |
C1—C7 | 1.514 (5) | C9—H9A | 0.9600 |
C2—C3 | 1.387 (5) | C9—H9B | 0.9600 |
C2—H2A | 0.9300 | C9—H9C | 0.9600 |
C4—O1—H1 | 109.5 | C6—C5—H5 | 120.3 |
C7—O2—H2 | 109.5 | C1—C6—C5 | 121.6 (4) |
C9—N1—C8 | 115.2 (3) | C1—C6—H6 | 119.2 |
C9—N1—H1A | 108.5 | C5—C6—H6 | 119.2 |
C8—N1—H1A | 108.5 | O2—C7—C8 | 106.3 (3) |
C9—N1—H1B | 108.5 | O2—C7—C1 | 113.4 (3) |
C8—N1—H1B | 108.5 | C8—C7—C1 | 111.3 (4) |
H1A—N1—H1B | 107.5 | O2—C7—H7 | 108.6 |
C6—C1—C2 | 118.3 (4) | C8—C7—H7 | 108.6 |
C6—C1—C7 | 121.3 (4) | C1—C7—H7 | 108.6 |
C2—C1—C7 | 120.3 (4) | N1—C8—C7 | 110.9 (3) |
C1—C2—C3 | 120.8 (4) | N1—C8—H8A | 109.5 |
C1—C2—H2A | 119.6 | C7—C8—H8A | 109.5 |
C3—C2—H2A | 119.6 | N1—C8—H8B | 109.5 |
C4—C3—C2 | 119.9 (4) | C7—C8—H8B | 109.5 |
C4—C3—H3 | 120.1 | H8A—C8—H8B | 108.0 |
C2—C3—H3 | 120.1 | N1—C9—H9A | 109.5 |
C3—C4—C5 | 120.0 (4) | N1—C9—H9B | 109.5 |
C3—C4—O1 | 122.5 (4) | H9A—C9—H9B | 109.5 |
C5—C4—O1 | 117.6 (4) | N1—C9—H9C | 109.5 |
C4—C5—C6 | 119.4 (4) | H9A—C9—H9C | 109.5 |
C4—C5—H5 | 120.3 | H9B—C9—H9C | 109.5 |
C6—C1—C2—C3 | 0.4 (6) | C4—C5—C6—C1 | 0.8 (6) |
C7—C1—C2—C3 | −178.5 (4) | C6—C1—C7—O2 | −47.4 (5) |
C1—C2—C3—C4 | 0.5 (6) | C2—C1—C7—O2 | 131.5 (4) |
C2—C3—C4—C5 | −0.8 (6) | C6—C1—C7—C8 | 72.4 (5) |
C2—C3—C4—O1 | 179.0 (4) | C2—C1—C7—C8 | −108.7 (5) |
C3—C4—C5—C6 | 0.2 (6) | C9—N1—C8—C7 | 179.8 (4) |
O1—C4—C5—C6 | −179.7 (4) | O2—C7—C8—N1 | −58.2 (5) |
C2—C1—C6—C5 | −1.1 (6) | C1—C7—C8—N1 | 177.9 (3) |
C7—C1—C6—C5 | 177.9 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···Cl1i | 0.82 | 2.23 | 3.037 (3) | 168 |
N1—H1A···Cl1ii | 0.90 | 2.22 | 3.091 (4) | 163 |
N1—H1B···O2 | 0.90 | 2.42 | 2.769 (4) | 103 |
N1—H1B···Cl1iii | 0.90 | 2.31 | 3.161 (3) | 157 |
O2—H2···O1iv | 0.82 | 2.01 | 2.825 (5) | 171 |
C8—H8A···Cl1 | 0.97 | 2.82 | 3.603 (4) | 138 |
Symmetry codes: (i) x−1/2, −y+1/2, −z; (ii) x−1, y, z; (iii) −x+1, y−1/2, −z+1/2; (iv) x−1/2, −y−1/2, −z. |