organic compounds
1-(2-Chlorophenyl)-2-(isopropylamino)ethanol
aCollege of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou 310014, People's Republic of China, and bJinhua People's Hospital, Jinhua 321000, People's Republic of China
*Correspondence e-mail: fenghai289289@163.com
In the title compound, C11H16ClNO, the side chain of the ethylamine group is almost perpendicular to the benzene ring; the dihedral angle between the C/C/N plane of the ethylamine grouping and the benzene plane is 87.4 (2)°. An intramolecular N—H⋯O hydrogen bond occurs. In the molecules are connected weakly by O—H⋯N hydrogen bonds, forming a tetramer around the symmetry axis. The tetramers are linked weakly by a C—H⋯O hydrogen bond.
Related literature
For a related structure, see: Koorts & Caira (1985). For the synthesis of the title compound, see; Koshinaka et al. (1978).
Experimental
Crystal data
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Data collection: PROCESS-AUTO (Rigaku, 1998); cell PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
Supporting information
10.1107/S1600536809019953/is2416sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536809019953/is2416Isup2.hkl
Racemic clorprenaline hydrochloride (10 g, 0.047 mol), which was purchased from Hangzhou Chempro Tech Co., Inc. Hang Zhou, China, was dissolved in ethanol (100 ml) and NaOH (1.9 g, 0.047 mol) was dissolved in water (100 ml). The two solutions were mixed and the mixture was cooled for 3 h. The precipitate formed was filtered off, washed with water and dried. The crude product obtained was recrystallized from ethanol. Single crystals suitable for X-ray analysis were grown by slow evaporation at room temperature.
H atoms were placed in calculated positions and allowed to ride on their parent atoms with C—H = 0.93 (aromatic), 0.98 (methine), 0.97 (methylene), 0.96 (methyl), O—H = 0.82 and N—H = 0.858 Å, with Uiso(H) = 1.2 or 1.5 times Ueq of the parent atoms.
Data collection: PROCESS-AUTO (Rigaku, 1998); cell
PROCESS-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).Fig. 1. The molecular structure with atom labels, showing 40% probability displacement ellipsoids. | |
Fig. 2. A packing diagram, viewed down along the c axis. |
C11H16ClNO | Dx = 1.191 Mg m−3 |
Mr = 213.70 | Mo Kα radiation, λ = 0.71073 Å |
Tetragonal, P421c | Cell parameters from 13301 reflections |
Hall symbol: P -4 2n | θ = 3.3–27.4° |
a = 14.0195 (5) Å | µ = 0.29 mm−1 |
c = 12.1243 (4) Å | T = 296 K |
V = 2382.99 (14) Å3 | Block, colorless |
Z = 8 | 0.41 × 0.38 × 0.22 mm |
F(000) = 912 |
Rigaku R-AXIS RAPID diffractometer | 2711 independent reflections |
Radiation source: RT | 1796 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.044 |
Detector resolution: 10.00 pixels mm-1 | θmax = 27.4°, θmin = 3.3° |
ω scans | h = −18→17 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −18→18 |
Tmin = 0.871, Tmax = 0.939 | l = −13→15 |
22063 measured reflections |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.043 | w = 1/[σ2(Fo2) + (0.002P)2 + 1.96P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.098 | (Δ/σ)max < 0.001 |
S = 1.00 | Δρmax = 0.19 e Å−3 |
2711 reflections | Δρmin = −0.33 e Å−3 |
131 parameters | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0308 (10) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983), 1181 Friedel pairs |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.001 (1) |
C11H16ClNO | Z = 8 |
Mr = 213.70 | Mo Kα radiation |
Tetragonal, P421c | µ = 0.29 mm−1 |
a = 14.0195 (5) Å | T = 296 K |
c = 12.1243 (4) Å | 0.41 × 0.38 × 0.22 mm |
V = 2382.99 (14) Å3 |
Rigaku R-AXIS RAPID diffractometer | 2711 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 1796 reflections with I > 2σ(I) |
Tmin = 0.871, Tmax = 0.939 | Rint = 0.044 |
22063 measured reflections |
R[F2 > 2σ(F2)] = 0.043 | H-atom parameters constrained |
wR(F2) = 0.098 | Δρmax = 0.19 e Å−3 |
S = 1.00 | Δρmin = −0.33 e Å−3 |
2711 reflections | Absolute structure: Flack (1983), 1181 Friedel pairs |
131 parameters | Absolute structure parameter: 0.001 (1) |
0 restraints |
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 | ||
Cl1 | 0.89802 (8) | 0.90968 (7) | 0.76779 (8) | 0.0866 (3) | |
O1 | 0.82940 (16) | 1.14673 (15) | 0.54268 (18) | 0.0616 (6) | |
H201 | 0.8801 | 1.1727 | 0.5581 | 0.074* | |
C2 | 0.81036 (19) | 1.07851 (19) | 0.7258 (2) | 0.0484 (6) | |
C1 | 0.8209 (2) | 1.06095 (19) | 0.6030 (2) | 0.0492 (7) | |
H1 | 0.8769 | 1.0208 | 0.5896 | 0.059* | |
N1 | 0.74199 (17) | 0.99152 (18) | 0.4402 (2) | 0.0527 (6) | |
H301 | 0.7679 | 1.0439 | 0.4192 | 0.063* | |
C4 | 0.8307 (3) | 1.0339 (3) | 0.9173 (3) | 0.0717 (10) | |
H4 | 0.8532 | 0.9910 | 0.9697 | 0.086* | |
C3 | 0.8417 (2) | 1.0153 (2) | 0.8060 (2) | 0.0557 (7) | |
C8 | 0.7325 (2) | 1.0115 (2) | 0.5591 (2) | 0.0538 (7) | |
H8A | 0.7227 | 0.9521 | 0.5987 | 0.065* | |
H8B | 0.6772 | 1.0517 | 0.5714 | 0.065* | |
C9 | 0.6502 (2) | 0.9762 (2) | 0.3839 (3) | 0.0658 (9) | |
H9 | 0.6062 | 1.0272 | 0.4054 | 0.079* | |
C7 | 0.7657 (2) | 1.1617 (2) | 0.7621 (3) | 0.0649 (8) | |
H7 | 0.7436 | 1.2054 | 0.7104 | 0.078* | |
C11 | 0.6655 (3) | 0.9809 (3) | 0.2604 (3) | 0.0907 (12) | |
H11A | 0.7094 | 0.9319 | 0.2385 | 0.109* | |
H11B | 0.6911 | 1.0422 | 0.2411 | 0.109* | |
H11C | 0.6057 | 0.9717 | 0.2233 | 0.109* | |
C6 | 0.7534 (2) | 1.1809 (3) | 0.8735 (3) | 0.0753 (10) | |
H6 | 0.7233 | 1.2367 | 0.8959 | 0.090* | |
C10 | 0.6073 (3) | 0.8813 (3) | 0.4176 (3) | 0.0885 (12) | |
H10A | 0.5965 | 0.8810 | 0.4958 | 0.106* | |
H10B | 0.6505 | 0.8307 | 0.3986 | 0.106* | |
H10C | 0.5479 | 0.8721 | 0.3798 | 0.106* | |
C5 | 0.7860 (3) | 1.1172 (3) | 0.9497 (3) | 0.0779 (11) | |
H5 | 0.7781 | 1.1300 | 1.0244 | 0.093* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.1254 (9) | 0.0656 (5) | 0.0688 (5) | 0.0248 (5) | −0.0095 (6) | 0.0035 (5) |
O1 | 0.0652 (14) | 0.0607 (13) | 0.0588 (12) | −0.0115 (10) | −0.0115 (11) | 0.0144 (10) |
C2 | 0.0470 (14) | 0.0513 (15) | 0.0470 (14) | −0.0033 (12) | 0.0018 (13) | −0.0009 (13) |
C1 | 0.0505 (16) | 0.0506 (16) | 0.0466 (15) | 0.0013 (13) | −0.0003 (13) | 0.0046 (12) |
N1 | 0.0532 (14) | 0.0547 (14) | 0.0501 (13) | −0.0047 (12) | −0.0052 (11) | −0.0027 (12) |
C4 | 0.086 (3) | 0.082 (3) | 0.0473 (18) | −0.006 (2) | −0.0079 (17) | −0.0014 (16) |
C3 | 0.0620 (18) | 0.0542 (17) | 0.0509 (16) | −0.0040 (15) | −0.0033 (14) | 0.0002 (13) |
C8 | 0.0536 (17) | 0.0556 (17) | 0.0522 (16) | −0.0052 (14) | 0.0036 (14) | −0.0057 (14) |
C9 | 0.0605 (19) | 0.062 (2) | 0.075 (2) | 0.0040 (16) | −0.0155 (17) | −0.0085 (16) |
C7 | 0.0632 (19) | 0.0651 (19) | 0.066 (2) | 0.0135 (15) | 0.0028 (17) | −0.0066 (17) |
C11 | 0.106 (3) | 0.092 (3) | 0.074 (2) | 0.004 (2) | −0.032 (2) | −0.007 (2) |
C6 | 0.065 (2) | 0.086 (3) | 0.075 (2) | 0.0079 (19) | 0.0035 (19) | −0.025 (2) |
C10 | 0.070 (2) | 0.085 (3) | 0.110 (3) | −0.021 (2) | −0.011 (2) | −0.007 (2) |
C5 | 0.075 (2) | 0.104 (3) | 0.0548 (19) | −0.012 (2) | 0.0057 (18) | −0.025 (2) |
Cl1—C3 | 1.741 (3) | C8—H8B | 0.9700 |
O1—C1 | 1.413 (3) | C9—C10 | 1.516 (5) |
O1—H201 | 0.8200 | C9—C11 | 1.514 (5) |
C2—C3 | 1.387 (4) | C9—H9 | 0.9800 |
C2—C7 | 1.395 (4) | C7—C6 | 1.387 (5) |
C2—C1 | 1.516 (4) | C7—H7 | 0.9300 |
C1—C8 | 1.517 (4) | C11—H11A | 0.9600 |
C1—H1 | 0.9800 | C11—H11B | 0.9600 |
N1—C9 | 1.473 (4) | C11—H11C | 0.9600 |
N1—C8 | 1.475 (4) | C6—C5 | 1.364 (5) |
N1—H301 | 0.8580 | C6—H6 | 0.9300 |
C4—C5 | 1.382 (5) | C10—H10A | 0.9600 |
C4—C3 | 1.383 (4) | C10—H10B | 0.9600 |
C4—H4 | 0.9300 | C10—H10C | 0.9600 |
C8—H8A | 0.9700 | C5—H5 | 0.9300 |
C1—O1—H201 | 109.5 | N1—C9—C11 | 109.2 (3) |
C3—C2—C7 | 117.1 (3) | C10—C9—C11 | 111.2 (3) |
C3—C2—C1 | 123.6 (3) | N1—C9—H9 | 108.7 |
C7—C2—C1 | 119.3 (3) | C10—C9—H9 | 108.7 |
O1—C1—C8 | 106.1 (2) | C11—C9—H9 | 108.7 |
O1—C1—C2 | 112.2 (2) | C6—C7—C2 | 121.7 (3) |
C8—C1—C2 | 109.8 (2) | C6—C7—H7 | 119.2 |
O1—C1—H1 | 109.6 | C2—C7—H7 | 119.2 |
C8—C1—H1 | 109.6 | C9—C11—H11A | 109.5 |
C2—C1—H1 | 109.6 | C9—C11—H11B | 109.5 |
C9—N1—C8 | 113.7 (2) | H11A—C11—H11B | 109.5 |
C9—N1—H301 | 110.9 | C9—C11—H11C | 109.5 |
C8—N1—H301 | 99.5 | H11A—C11—H11C | 109.5 |
C5—C4—C3 | 119.2 (3) | H11B—C11—H11C | 109.5 |
C5—C4—H4 | 120.4 | C5—C6—C7 | 119.4 (3) |
C3—C4—H4 | 120.4 | C5—C6—H6 | 120.3 |
C4—C3—C2 | 121.9 (3) | C7—C6—H6 | 120.3 |
C4—C3—Cl1 | 118.1 (3) | C9—C10—H10A | 109.5 |
C2—C3—Cl1 | 120.0 (2) | C9—C10—H10B | 109.5 |
N1—C8—C1 | 110.9 (2) | H10A—C10—H10B | 109.5 |
N1—C8—H8A | 109.5 | C9—C10—H10C | 109.5 |
C1—C8—H8A | 109.5 | H10A—C10—H10C | 109.5 |
N1—C8—H8B | 109.5 | H10B—C10—H10C | 109.5 |
C1—C8—H8B | 109.5 | C6—C5—C4 | 120.8 (3) |
H8A—C8—H8B | 108.1 | C6—C5—H5 | 119.6 |
N1—C9—C10 | 110.5 (3) | C4—C5—H5 | 119.6 |
C3—C2—C1—O1 | −150.5 (3) | C9—N1—C8—C1 | −159.3 (3) |
C7—C2—C1—O1 | 30.5 (4) | O1—C1—C8—N1 | 59.9 (3) |
C3—C2—C1—C8 | 91.8 (3) | C2—C1—C8—N1 | −178.6 (2) |
C7—C2—C1—C8 | −87.2 (3) | C8—N1—C9—C10 | −71.4 (4) |
C5—C4—C3—C2 | 1.0 (5) | C8—N1—C9—C11 | 166.0 (3) |
C5—C4—C3—Cl1 | −179.8 (3) | C3—C2—C7—C6 | 0.3 (5) |
C7—C2—C3—C4 | −0.9 (5) | C1—C2—C7—C6 | 179.4 (3) |
C1—C2—C3—C4 | −180.0 (3) | C2—C7—C6—C5 | 0.2 (5) |
C7—C2—C3—Cl1 | 179.9 (2) | C7—C6—C5—C4 | −0.2 (6) |
C1—C2—C3—Cl1 | 0.9 (4) | C3—C4—C5—C6 | −0.4 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H201···N1i | 0.82 | 1.97 | 2.765 (3) | 164 |
N1—H301···O1 | 0.86 | 2.25 | 2.789 (3) | 121 |
C6—H6···O1ii | 0.93 | 2.45 | 3.283 (4) | 149 |
Symmetry codes: (i) y, −x+2, −z+1; (ii) y−1/2, x+1/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C11H16ClNO |
Mr | 213.70 |
Crystal system, space group | Tetragonal, P421c |
Temperature (K) | 296 |
a, c (Å) | 14.0195 (5), 12.1243 (4) |
V (Å3) | 2382.99 (14) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.29 |
Crystal size (mm) | 0.41 × 0.38 × 0.22 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID diffractometer |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.871, 0.939 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 22063, 2711, 1796 |
Rint | 0.044 |
(sin θ/λ)max (Å−1) | 0.648 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.043, 0.098, 1.00 |
No. of reflections | 2711 |
No. of parameters | 131 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.19, −0.33 |
Absolute structure | Flack (1983), 1181 Friedel pairs |
Absolute structure parameter | 0.001 (1) |
Computer programs: PROCESS-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2004), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H201···N1i | 0.82 | 1.97 | 2.765 (3) | 164 |
N1—H301···O1 | 0.86 | 2.25 | 2.789 (3) | 121 |
C6—H6···O1ii | 0.93 | 2.45 | 3.283 (4) | 149 |
Symmetry codes: (i) y, −x+2, −z+1; (ii) y−1/2, x+1/2, z+1/2. |
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
The title compound (clorprenaline) is one of a series of structurally related β-adrenoceptorblocking drugs. Synthesis results have been reported in the literature (Koshinaka et al., 1978). Clorprenaline was prepared by clorprenaline hydrochloride.
In the title compound (Fig. 1), there are no unusual bond distances or angles. The Cl atom and the phenyl plane is almost planar with the deviation of 0.0026 Å. The dihedral angle between the plane formed by C1 C2 C8 and the phenyl plane is 87.5°, which shows that the two planes are almost perpendicular. The C9—N1 distance of 1.473 (4) Å is shorter than the value of the similar bond distance of 1.502 Å (Koorts & Caira, 1985). The crystal structure indicates a possible intermolecular O—H···N interaction that might help to establish the crystal packing (Fig. 2).