Literature DB >> 21587582

N-[2-(2-Chloro-phen-yl)-2-hy-droxy-eth-yl]propan-2-aminium 4-methyl-benzoate.

Hai Feng1, Bin Tao Xing, Xin Huang, Ya Jian Zhou, Ying Song.   

Abstract

The title compound, C(11)H(17)ClNO(+)·C(8)H(7)O(2) (-), was obtained by the reaction of chlorprenaline {or 1-(2-chloro-phen-yl)-2-[(1-methyl-eth-yl)amino]-ethanol} and p-toluic acid. The chlorpren-aline is twisted moderately with a C-C-C-C torsion angle of 109.6 (2)°. The two mol-ecules are linked by classical O-H⋯O and N-H⋯O hydrogen bonds. Further N-H⋯O hydrogen bonds link two of these units into dimers.

Entities:  

Year:  2010        PMID： 21587582      PMCID： PMC2983265          DOI： 10.1107/S1600536810033878

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For related structures, see: Feng et al. (2010 ▶); Takwale & Pant (1971 ▶); Tang et al. (2009a ▶,b ▶).

Experimental

Crystal data

C11H17ClNO+·C8H7O2 − M = 349.84 Monoclinic, a = 8.5966 (4) Å b = 8.1288 (3) Å c = 26.8949 (12) Å β = 91.600 (1)° V = 1878.68 (14) Å3 Z = 4 Mo Kα radiation μ = 0.22 mm−1 T = 296 K 0.37 × 0.30 × 0.22 mm

Data collection

Rigaku R-AXIS RAPID/ZJUG CCD diffractometer Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.913, T max = 0.953 27924 measured reflections 4271 independent reflections 2763 reflections with I > 2σ(I) R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.042 wR(F 2) = 0.125 S = 1.00 4271 reflections 222 parameters H-atom parameters constrained Δρmax = 0.21 e Å−3 Δρmin = −0.31 e Å−3 Data collection: PROCESS-AUTO (Rigaku/MSC, 2006 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2007 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810033878/rk2225sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810033878/rk2225Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C11H17ClNO+·C8H7O2−F(000) = 744
Mr = 349.84Dx = 1.237 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 17098 reflections
a = 8.5966 (4) Åθ = 3.0–27.4°
b = 8.1288 (3) ŵ = 0.22 mm−1
c = 26.8949 (12) ÅT = 296 K
β = 91.600 (1)°Chunk, colourless
V = 1878.68 (14) Å30.37 × 0.30 × 0.22 mm
Z = 4
Rigaku R-AXIS RAPID/ZJUG CCD diffractometer4271 independent reflections
Radiation source: rotate anode2763 reflections with I > 2σ(I)
graphiteRint = 0.036
Detector resolution: 10.00 pixels mm-1θmax = 27.4°, θmin = 3.0°
φ and ω scansh = −11→11
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)k = −10→9
Tmin = 0.913, Tmax = 0.953l = −34→34
27924 measured reflections
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042H-atom parameters constrained
wR(F2) = 0.125w = 1/[σ2(Fo2) + (0.0502P)2 + 0.6753P] where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
4271 reflectionsΔρmax = 0.21 e Å−3
222 parametersΔρmin = −0.31 e Å−3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0084 (10)
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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.
xyzUiso*/Ueq
Cl10.29951 (9)0.54161 (7)0.65218 (2)0.0833 (2)
O10.27619 (16)0.21200 (19)0.53119 (5)0.0615 (4)
H1010.28030.27540.50760.092*
O20.49211 (17)0.21720 (18)0.43539 (5)0.0619 (4)
N10.62036 (16)0.27020 (17)0.53021 (5)0.0420 (3)
H1020.63830.37830.53480.050*
H1030.56190.25920.50210.050*
C70.2495 (2)0.3348 (2)0.65680 (7)0.0541 (5)
C10.3646 (2)0.2763 (2)0.57188 (6)0.0440 (4)
H10.36780.39660.56960.053*
C20.2854 (2)0.2261 (2)0.61907 (6)0.0459 (4)
C80.5294 (2)0.2082 (2)0.57268 (6)0.0486 (4)
H8A0.58200.23920.60370.058*
H8B0.52520.08910.57130.058*
C90.7739 (2)0.1855 (3)0.52294 (8)0.0571 (5)
H90.75330.07260.51180.068*
C40.1703 (3)0.0101 (3)0.66772 (10)0.0788 (7)
H40.1439−0.10010.67140.095*
C60.1758 (3)0.2841 (3)0.69932 (8)0.0749 (7)
H60.15400.35920.72430.090*
C100.8567 (3)0.2759 (3)0.48204 (9)0.0744 (6)
H10A0.79010.28100.45280.112*
H10B0.95070.21860.47450.112*
H10C0.88170.38550.49300.112*
C30.2444 (2)0.0620 (3)0.62573 (8)0.0607 (5)
H30.2677−0.01430.60130.073*
C110.8699 (3)0.1785 (4)0.57050 (10)0.0913 (8)
H11A0.88040.28730.58410.137*
H11B0.97110.13530.56380.137*
H11C0.81960.10860.59390.137*
C50.1353 (3)0.1218 (3)0.70422 (9)0.0830 (8)
H50.08400.08710.73230.100*
O30.30804 (17)0.40215 (16)0.44986 (5)0.0589 (4)
C130.3104 (2)0.2771 (2)0.37008 (6)0.0439 (4)
C120.3761 (2)0.3002 (2)0.42202 (6)0.0467 (4)
C140.3905 (2)0.1855 (2)0.33582 (7)0.0547 (5)
H140.48420.13600.34530.066*
C180.1687 (2)0.3448 (2)0.35524 (7)0.0529 (5)
H180.11170.40520.37780.064*
C160.1925 (2)0.2349 (3)0.27234 (7)0.0578 (5)
C150.3330 (3)0.1666 (3)0.28760 (7)0.0609 (5)
H150.39010.10670.26500.073*
C170.1113 (2)0.3231 (3)0.30701 (7)0.0607 (5)
H170.01570.36900.29780.073*
C190.1321 (4)0.2139 (4)0.21933 (9)0.0890 (8)
H19A0.20180.26670.19710.133*
H19B0.03080.26290.21580.133*
H19C0.12540.09890.21150.133*
U11U22U33U12U13U23
Cl10.1200 (5)0.0570 (3)0.0746 (4)−0.0060 (3)0.0327 (3)−0.0103 (3)
O10.0601 (8)0.0804 (10)0.0435 (7)−0.0112 (7)−0.0052 (6)0.0058 (7)
O20.0651 (9)0.0754 (9)0.0446 (7)0.0106 (7)−0.0091 (6)−0.0056 (7)
N10.0427 (8)0.0434 (8)0.0400 (7)0.0015 (6)0.0020 (6)−0.0029 (6)
C70.0561 (11)0.0568 (11)0.0498 (10)0.0044 (9)0.0102 (8)0.0035 (9)
C10.0488 (10)0.0454 (9)0.0378 (8)0.0003 (7)0.0026 (7)0.0009 (7)
C20.0460 (10)0.0515 (10)0.0404 (9)0.0035 (8)0.0026 (7)0.0067 (8)
C80.0497 (10)0.0523 (10)0.0440 (9)0.0024 (8)0.0034 (8)0.0064 (8)
C90.0487 (11)0.0585 (12)0.0643 (12)0.0116 (9)0.0063 (9)−0.0040 (9)
C40.0927 (17)0.0631 (14)0.0818 (16)−0.0038 (12)0.0234 (13)0.0242 (12)
C60.0881 (17)0.0820 (16)0.0561 (12)0.0105 (13)0.0285 (12)0.0043 (11)
C100.0552 (13)0.0929 (17)0.0761 (15)0.0067 (12)0.0194 (11)−0.0026 (13)
C30.0708 (13)0.0549 (12)0.0570 (12)−0.0008 (10)0.0103 (10)0.0072 (9)
C110.0580 (14)0.131 (2)0.0845 (17)0.0235 (15)−0.0098 (12)0.0098 (16)
C50.0928 (18)0.0889 (18)0.0691 (15)0.0057 (14)0.0357 (13)0.0274 (13)
O30.0889 (10)0.0460 (7)0.0420 (7)0.0038 (7)0.0029 (6)−0.0067 (6)
C130.0538 (10)0.0406 (9)0.0375 (8)−0.0040 (7)0.0015 (7)0.0012 (7)
C120.0616 (11)0.0399 (9)0.0388 (9)−0.0050 (8)0.0023 (8)−0.0008 (7)
C140.0567 (11)0.0613 (12)0.0460 (10)0.0066 (9)−0.0016 (8)−0.0078 (9)
C180.0578 (12)0.0537 (11)0.0475 (10)0.0037 (9)0.0053 (8)0.0015 (8)
C160.0710 (13)0.0594 (12)0.0426 (10)−0.0094 (10)−0.0061 (9)0.0016 (9)
C150.0716 (14)0.0698 (13)0.0414 (10)0.0016 (11)0.0039 (9)−0.0116 (9)
C170.0597 (12)0.0664 (13)0.0555 (11)0.0027 (10)−0.0051 (9)0.0076 (10)
C190.114 (2)0.0984 (19)0.0531 (13)−0.0079 (16)−0.0230 (13)−0.0049 (13)
Cl1—C71.741 (2)C10—H10A0.9600
O1—C11.415 (2)C10—H10B0.9600
O1—H1010.8200C10—H10C0.9600
O2—C121.248 (2)C3—H30.9300
N1—C81.490 (2)C11—H11A0.9600
N1—C91.507 (2)C11—H11B0.9600
N1—H1020.9000C11—H11C0.9600
N1—H1030.9000C5—H50.9300
C7—C61.386 (3)O3—C121.271 (2)
C7—C21.387 (3)C13—C141.383 (2)
C1—C21.513 (2)C13—C181.386 (3)
C1—C81.521 (2)C13—C121.504 (2)
C1—H10.9800C14—C151.384 (3)
C2—C31.392 (3)C14—H140.9300
C8—H8A0.9700C18—C171.386 (3)
C8—H8B0.9700C18—H180.9300
C9—C111.504 (3)C16—C171.381 (3)
C9—C101.517 (3)C16—C151.382 (3)
C9—H90.9800C16—C191.513 (3)
C4—C51.376 (4)C15—H150.9300
C4—C31.379 (3)C17—H170.9300
C4—H40.9300C19—H19A0.9600
C6—C51.371 (4)C19—H19B0.9600
C6—H60.9300C19—H19C0.9600
C1—O1—H101109.5H10A—C10—H10C109.5
C8—N1—C9115.19 (14)H10B—C10—H10C109.5
C8—N1—H102108.5C4—C3—C2121.5 (2)
C9—N1—H102108.5C4—C3—H3119.2
C8—N1—H103108.5C2—C3—H3119.2
C9—N1—H103108.5C9—C11—H11A109.5
H102—N1—H103107.5C9—C11—H11B109.5
C6—C7—C2122.1 (2)H11A—C11—H11B109.5
C6—C7—Cl1117.75 (17)C9—C11—H11C109.5
C2—C7—Cl1120.19 (14)H11A—C11—H11C109.5
O1—C1—C2107.74 (14)H11B—C11—H11C109.5
O1—C1—C8110.88 (15)C6—C5—C4120.3 (2)
C2—C1—C8109.32 (14)C6—C5—H5119.8
O1—C1—H1109.6C4—C5—H5119.8
C2—C1—H1109.6C14—C13—C18118.17 (16)
C8—C1—H1109.6C14—C13—C12120.33 (16)
C7—C2—C3117.01 (17)C18—C13—C12121.50 (16)
C7—C2—C1123.81 (17)O2—C12—O3124.06 (16)
C3—C2—C1119.18 (17)O2—C12—C13118.45 (16)
N1—C8—C1112.01 (14)O3—C12—C13117.49 (16)
N1—C8—H8A109.2C13—C14—C15120.84 (18)
C1—C8—H8A109.2C13—C14—H14119.6
N1—C8—H8B109.2C15—C14—H14119.6
C1—C8—H8B109.2C13—C18—C17120.41 (18)
H8A—C8—H8B107.9C13—C18—H18119.8
C11—C9—N1111.64 (17)C17—C18—H18119.8
C11—C9—C10112.2 (2)C17—C16—C15117.54 (17)
N1—C9—C10107.65 (16)C17—C16—C19121.9 (2)
C11—C9—H9108.4C15—C16—C19120.6 (2)
N1—C9—H9108.4C16—C15—C14121.36 (19)
C10—C9—H9108.4C16—C15—H15119.3
C5—C4—C3119.8 (2)C14—C15—H15119.3
C5—C4—H4120.1C16—C17—C18121.64 (19)
C3—C4—H4120.1C16—C17—H17119.2
C5—C6—C7119.2 (2)C18—C17—H17119.2
C5—C6—H6120.4C16—C19—H19A109.5
C7—C6—H6120.4C16—C19—H19B109.5
C9—C10—H10A109.5H19A—C19—H19B109.5
C9—C10—H10B109.5C16—C19—H19C109.5
H10A—C10—H10B109.5H19A—C19—H19C109.5
C9—C10—H10C109.5H19B—C19—H19C109.5
C6—C7—C2—C3−0.2 (3)C1—C2—C3—C4−179.13 (19)
Cl1—C7—C2—C3178.83 (15)C7—C6—C5—C41.2 (4)
C6—C7—C2—C1179.50 (19)C3—C4—C5—C6−0.9 (4)
Cl1—C7—C2—C1−1.4 (3)C14—C13—C12—O2−9.8 (3)
O1—C1—C2—C7−129.79 (18)C18—C13—C12—O2169.70 (18)
C8—C1—C2—C7109.6 (2)C14—C13—C12—O3171.21 (17)
O1—C1—C2—C349.9 (2)C18—C13—C12—O3−9.3 (3)
C8—C1—C2—C3−70.6 (2)C18—C13—C14—C152.1 (3)
C9—N1—C8—C1−169.34 (15)C12—C13—C14—C15−178.45 (18)
O1—C1—C8—N168.35 (19)C14—C13—C18—C17−1.1 (3)
C2—C1—C8—N1−173.02 (14)C12—C13—C18—C17179.36 (17)
C8—N1—C9—C11−50.6 (2)C17—C16—C15—C140.0 (3)
C8—N1—C9—C10−174.10 (16)C19—C16—C15—C14179.6 (2)
C2—C7—C6—C5−0.7 (4)C13—C14—C15—C16−1.5 (3)
Cl1—C7—C6—C5−179.8 (2)C15—C16—C17—C180.9 (3)
C5—C4—C3—C2−0.1 (4)C19—C16—C17—C18−178.6 (2)
C7—C2—C3—C40.6 (3)C13—C18—C17—C16−0.3 (3)
D—H···AD—HH···AD···AD—H···A
O1—H101···O30.821.882.6986 (18)173
N1—H103···O20.901.912.7835 (18)164
N1—H102···O3i0.901.892.7824 (19)174
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
O1—H101⋯O30.821.882.6986 (18)173
N1—H103⋯O20.901.912.7835 (18)164
N1—H102⋯O3i0.901.892.7824 (19)174

Symmetry code: (i) .

  4 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

2.  N-[2-(2-Chloro-phen-yl)-2-hydroxy-ethyl]propan-2-aminium hemioxalate.

Authors:  Zhan Tang; Min Xu; Hui-Cheng Zhang; Hai Feng
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-06-24

3.  1-(2-Chloro-phen-yl)-2-(isopropyl-amino)ethanol.

Authors:  Zhan Tang; Min Xu; Gui-Ru Zheng; Hai Feng
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-06-06

4.  N-[2-(2-Chloro-phen-yl)-2-hydroxy-ethyl]propan-2-aminium nitrate.

Authors:  Hai Feng; Zhan Tang; Lin-Jun Xie; Bin-Tao Xing
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-01-16
  4 in total
  1 in total

1.  [2-(2-Chloro-phen-yl)-2-hy-droxy-eth-yl](isoprop-yl)ammonium 4-hy-droxy-benzoate.

Authors:  Ling Zhou; Yang Guang Qi; Ge Zhang; Yu Yun Xu; Hai Feng
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-12-18
  1 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.