Literature DB >> 21587515

N-Benzyl-2-(3-chloro-4-hy-droxy-phen-yl)acetamide.

Rohan A Davis, Peter C Healy.   

Abstract

The title compound, C(15)H(14)ClNO(2), was synthesized as part of a project to generate a combinatorial library based on the fungal natural product 2-(3-chloro-4-hy-droxy-phen-yl)acetamide. It crystallizes as non-planar discrete mol-ecules [the peripheral 3-chloro-4-hy-droxy-phenyl and benzyl groups are twisted out of the plane of the central acetamide group, with N-C-C-C and C-C-C-C torsion angles of -58.8 (3) and 65.0 (2)°, respectively] linked by inter-molecular N-H⋯O and O-H⋯O hydrogen bonds.

Entities:  

Year:  2010        PMID： 21587515      PMCID： PMC2983291          DOI： 10.1107/S1600536810035397

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


Related literature

For the preparation and characterization of the title compound, see: Poulsen et al. (2006 ▶); Davis et al. (2007 ▶). For the biological activity of the title compound, see: Davis et al. (2005 ▶, 2007 ▶). For background to organohalogen natural products, see: Gribble (1996 ▶). For related structures having the 3-chloro-4-hy­droxy­phenyl­acetamide moiety, see: Krohn et al. (1992 ▶); Davis et al. (2005 ▶); Davis & Healy (2008 ▶).

Experimental

Crystal data

C15H14ClNO2 M = 275.72 Monoclinic, a = 4.8255 (2) Å b = 10.8520 (5) Å c = 12.7701 (6) Å β = 96.055 (4)° V = 664.99 (5) Å3 Z = 2 Mo Kα radiation μ = 0.28 mm−1 T = 296 K 0.55 × 0.40 × 0.04 mm

Data collection

Oxford-Diffraction Gemini S Ultra diffractometer Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.859, T max = 0.989 4800 measured reflections 2334 independent reflections 1979 reflections with I > 2σ(I) R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.030 wR(F 2) = 0.070 S = 0.96 2334 reflections 172 parameters 1 restraint H-atom parameters constrained Δρmax = 0.13 e Å−3 Δρmin = −0.15 e Å−3 Absolute structure: Flack (1983 ▶), 1098 Friedel pairs Flack parameter: −0.11 (6) Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810035397/tk2709sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810035397/tk2709Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C15H14ClNO2F(000) = 288
Mr = 275.72Dx = 1.377 Mg m−3
Monoclinic, P21Mo Kα radiation, λ = 0.71070 Å
Hall symbol: P 2ybCell parameters from 2771 reflections
a = 4.8255 (2) Åθ = 3.2–32.2°
b = 10.8520 (5) ŵ = 0.28 mm−1
c = 12.7701 (6) ÅT = 296 K
β = 96.055 (4)°Plate, colourless
V = 664.99 (5) Å30.55 × 0.40 × 0.04 mm
Z = 2
Oxford-Diffraction Gemini S Ultra diffractometer2334 independent reflections
Radiation source: Enhance (Mo) X-ray Source1979 reflections with I > 2σ(I)
graphiteRint = 0.020
Detector resolution: 16.0774 pixels mm-1θmax = 25.0°, θmin = 3.2°
ω and φ scansh = −5→5
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)k = −12→12
Tmin = 0.859, Tmax = 0.989l = −15→12
4800 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)] = 0.030H-atom parameters constrained
wR(F2) = 0.070w = 1/[σ2(Fo2) + (0.0444P)2] where P = (Fo2 + 2Fc2)/3
S = 0.96(Δ/σ)max = 0.002
2334 reflectionsΔρmax = 0.13 e Å−3
172 parametersΔρmin = −0.15 e Å−3
1 restraintAbsolute structure: Flack (1983), 1098 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: −0.11 (6)
Experimental. CrysAlisPro (Oxford Diffraction, 2010). Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
Cl3−0.22153 (16)0.10603 (6)0.70233 (4)0.0799 (3)
O4−0.5174 (3)0.33833 (14)0.69050 (12)0.0612 (6)
O8−0.3412 (2)0.08182 (14)0.27899 (10)0.0506 (5)
N10.0633 (3)0.05425 (16)0.21183 (12)0.0452 (5)
C1−0.1150 (4)0.25973 (19)0.42574 (15)0.0386 (6)
C2−0.1047 (4)0.1808 (2)0.51082 (16)0.0449 (7)
C3−0.2387 (4)0.20842 (19)0.59745 (15)0.0452 (7)
C4−0.3886 (4)0.31713 (18)0.60254 (15)0.0431 (7)
C5−0.3982 (4)0.39584 (19)0.51848 (17)0.0480 (7)
C6−0.2645 (4)0.36758 (19)0.43020 (16)0.0469 (7)
C70.0273 (4)0.2253 (2)0.33001 (16)0.0462 (7)
C8−0.0977 (3)0.1137 (2)0.27214 (13)0.0366 (6)
C9−0.0319 (5)−0.0518 (2)0.14734 (18)0.0568 (8)
C100.1377 (4)−0.06951 (19)0.05671 (16)0.0412 (7)
C110.1558 (4)0.0217 (2)−0.01686 (18)0.0577 (8)
C120.3073 (5)0.0053 (2)−0.10153 (19)0.0663 (9)
C130.4390 (5)−0.1045 (3)−0.11432 (19)0.0643 (9)
C140.4229 (5)−0.1963 (2)−0.04274 (19)0.0660 (9)
C150.2735 (5)−0.1792 (2)0.04367 (18)0.0531 (8)
H10.231700.078400.209900.0540*
H2−0.004400.105900.509300.0540*
H4−0.564400.419100.700500.0730*
H5−0.499400.470800.520800.0570*
H6−0.273800.422900.372900.0580*
H110.061900.09810−0.008300.0710*
H120.316400.06970−0.151800.0840*
H130.54640−0.11580−0.170200.0790*
H140.50880−0.27320−0.052000.0800*
H150.26570−0.242600.093800.0660*
H710.015800.293200.283100.0550*
H720.217600.208100.352600.0550*
H91−0.22280−0.039500.121100.0690*
H92−0.01890−0.123900.190400.0690*
U11U22U33U12U13U23
Cl30.1357 (6)0.0590 (4)0.0499 (3)0.0134 (4)0.0333 (3)0.0106 (3)
O40.0733 (10)0.0631 (10)0.0523 (9)0.0062 (8)0.0312 (8)−0.0102 (8)
O80.0325 (6)0.0649 (11)0.0572 (8)−0.0121 (6)0.0183 (6)−0.0131 (7)
N10.0279 (7)0.0588 (11)0.0510 (10)−0.0130 (7)0.0142 (7)−0.0190 (9)
C10.0343 (9)0.0426 (11)0.0406 (11)−0.0076 (8)0.0115 (8)−0.0073 (9)
C20.0506 (11)0.0393 (12)0.0464 (12)0.0077 (9)0.0128 (9)−0.0042 (10)
C30.0564 (12)0.0425 (11)0.0382 (11)−0.0023 (9)0.0124 (10)−0.0009 (9)
C40.0439 (11)0.0464 (12)0.0409 (11)0.0001 (9)0.0140 (9)−0.0086 (10)
C50.0495 (12)0.0446 (12)0.0515 (13)0.0108 (9)0.0133 (10)−0.0059 (11)
C60.0550 (12)0.0431 (12)0.0440 (12)−0.0021 (10)0.0122 (10)−0.0004 (10)
C70.0428 (10)0.0524 (13)0.0468 (11)−0.0101 (10)0.0201 (9)−0.0079 (10)
C80.0304 (9)0.0481 (11)0.0325 (9)−0.0038 (9)0.0095 (7)0.0021 (9)
C90.0489 (12)0.0657 (15)0.0591 (14)−0.0192 (10)0.0209 (11)−0.0221 (12)
C100.0353 (10)0.0465 (13)0.0426 (11)−0.0105 (9)0.0075 (8)−0.0099 (10)
C110.0580 (13)0.0485 (14)0.0683 (16)0.0089 (11)0.0151 (12)0.0015 (12)
C120.0759 (16)0.0680 (17)0.0571 (15)−0.0015 (13)0.0172 (13)0.0140 (13)
C130.0702 (15)0.0805 (19)0.0456 (13)−0.0025 (13)0.0221 (11)−0.0122 (13)
C140.0833 (18)0.0581 (16)0.0593 (15)0.0144 (12)0.0209 (13)−0.0156 (13)
C150.0693 (14)0.0426 (13)0.0482 (12)−0.0012 (10)0.0099 (10)−0.0025 (10)
Cl3—C31.736 (2)C10—C111.374 (3)
O4—C41.360 (2)C11—C121.379 (3)
O8—C81.2368 (18)C12—C131.368 (4)
O4—H40.9200C13—C141.360 (4)
N1—C81.319 (2)C14—C151.393 (3)
N1—C91.461 (3)C2—H20.9500
N1—H10.8600C5—H50.9500
C1—C71.511 (3)C6—H60.9400
C1—C61.379 (3)C7—H710.9500
C1—C21.380 (3)C7—H720.9500
C2—C31.372 (3)C9—H910.9600
C3—C41.389 (3)C9—H920.9500
C4—C51.369 (3)C11—H110.9600
C5—C61.391 (3)C12—H120.9500
C7—C81.511 (3)C13—H130.9300
C9—C101.499 (3)C14—H140.9400
C10—C151.377 (3)C15—H150.9400
Cl3···O42.8932 (17)H1···O8vii2.1500
Cl3···C12i3.554 (2)H1···C112.9500
Cl3···H12ii3.0800H1···H722.3100
Cl3···H12i3.0600H1···H4viii2.5500
Cl3···H15iii3.1000H2···C83.0200
O4···Cl32.8932 (17)H2···C5viii3.0400
O4···O8iv2.767 (2)H2···C6viii2.9600
O4···C9iv3.375 (3)H4···H52.4100
O4···C9iii3.403 (3)H4···O8iv1.8500
O8···O4v2.767 (2)H4···N1iii2.9500
O8···N1vi2.9262 (18)H4···C8iv2.7100
O8···C23.242 (2)H4···C9iv2.9100
O4···H92iii2.8900H4···H1iii2.5500
O4···H92iv2.8600H5···H42.4100
O8···H72vi2.7800H5···C2iv2.9700
O8···H912.5200H6···H712.3600
O8···H1vi2.1500H11···N12.8500
O8···H4v1.8500H11···C15xii2.9200
N1···O8vii2.9262 (18)H11···H14x2.5500
N1···H112.8500H11···H15xii2.5100
N1···H4viii2.9500H12···Cl3ix3.0600
C2···O83.242 (2)H12···Cl3xiii3.0800
C9···O4viii3.403 (3)H14···C11xiv2.8400
C9···O4v3.375 (3)H14···H11xiv2.5500
C12···Cl3ix3.554 (2)H15···H922.3300
C2···H5v2.9700H15···Cl3viii3.1000
C5···H2iii3.0400H15···H11xi2.5100
C6···H2iii2.9600H71···H62.3600
C8···H4v2.7100H72···O8vii2.7800
C8···H23.0200H72···H12.3100
C9···H4v2.9100H91···O82.5200
C11···H12.9500H91···C14vi3.0700
C11···H14x2.8400H91···C15vi2.9500
C14···H91vii3.0700H92···H152.3300
C15···H91vii2.9500H92···O4v2.8600
C15···H11xi2.9200H92···O4viii2.8900
C4—O4—H4115.00C10—C15—C14120.2 (2)
C8—N1—C9123.03 (16)C1—C2—H2119.00
C8—N1—H1119.00C3—C2—H2119.00
C9—N1—H1118.00C4—C5—H5119.00
C2—C1—C6118.01 (18)C6—C5—H5120.00
C2—C1—C7120.12 (18)C1—C6—H6119.00
C6—C1—C7121.85 (18)C5—C6—H6120.00
C1—C2—C3121.21 (19)C1—C7—H71109.00
C2—C3—C4121.02 (19)C1—C7—H72108.00
Cl3—C3—C2119.61 (16)C8—C7—H71109.00
Cl3—C3—C4119.37 (15)C8—C7—H72108.00
O4—C4—C3117.91 (17)H71—C7—H72110.00
O4—C4—C5124.18 (18)N1—C9—H91109.00
C3—C4—C5117.91 (18)N1—C9—H92109.00
C4—C5—C6121.19 (19)C10—C9—H91109.00
C1—C6—C5120.66 (19)C10—C9—H92109.00
C1—C7—C8113.70 (16)H91—C9—H92109.00
O8—C8—C7121.53 (16)C10—C11—H11119.00
O8—C8—N1121.81 (18)C12—C11—H11120.00
N1—C8—C7116.64 (15)C11—C12—H12120.00
N1—C9—C10111.81 (18)C13—C12—H12120.00
C9—C10—C11121.00 (19)C12—C13—H13121.00
C9—C10—C15120.65 (19)C14—C13—H13120.00
C11—C10—C15118.33 (19)C13—C14—H14120.00
C10—C11—C12121.4 (2)C15—C14—H14119.00
C11—C12—C13119.8 (2)C10—C15—H15120.00
C12—C13—C14119.8 (2)C14—C15—H15120.00
C13—C14—C15120.4 (2)
C8—N1—C9—C10156.64 (18)C3—C4—C5—C60.6 (3)
C9—N1—C8—O81.0 (3)O4—C4—C5—C6−179.11 (18)
C9—N1—C8—C7−177.14 (17)C4—C5—C6—C1−0.9 (3)
C6—C1—C2—C30.0 (3)C1—C7—C8—O823.7 (3)
C7—C1—C2—C3−178.18 (18)C1—C7—C8—N1−158.08 (17)
C2—C1—C6—C50.6 (3)N1—C9—C10—C11−58.8 (3)
C6—C1—C7—C8−113.1 (2)N1—C9—C10—C15122.9 (2)
C2—C1—C7—C865.0 (2)C9—C10—C15—C14177.8 (2)
C7—C1—C6—C5178.69 (18)C11—C10—C15—C14−0.5 (3)
C1—C2—C3—C4−0.2 (3)C9—C10—C11—C12−178.8 (2)
C1—C2—C3—Cl3179.67 (16)C15—C10—C11—C12−0.5 (3)
Cl3—C3—C4—O4−0.2 (3)C10—C11—C12—C131.2 (3)
C2—C3—C4—C5−0.1 (3)C11—C12—C13—C14−0.9 (4)
Cl3—C3—C4—C5−179.95 (15)C12—C13—C14—C15−0.1 (4)
C2—C3—C4—O4179.67 (18)C13—C14—C15—C100.8 (4)
D—H···AD—HH···AD···AD—H···A
N1—H1···O8vii0.862.152.9262 (18)150
O4—H4···O8iv0.921.852.767 (2)180
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N1—H1⋯O8i0.862.152.9262 (18)150
O4—H4⋯O8ii0.921.852.767 (2)180

Symmetry codes: (i) ; (ii) .

  6 in total

1.  Screening a natural product-based combinatorial library using FTICR mass spectrometry.

Authors:  Sally-Ann Poulsen; Rohan A Davis; Timothy G Keys
Journal:  Bioorg Med Chem       Date:  2005-09-29       Impact factor: 3.641

2.  Synthesis and spectroscopic characterisation of a combinatorial library based on the fungal natural product 3-chloro-4-hydroxyphenylacetamide.

Authors:  Rohan A Davis; Gregory K Pierens; Peter G Parsons
Journal:  Magn Reson Chem       Date:  2007-05       Impact factor: 2.447

3.  A short history of SHELX.

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

Review 4.  Naturally occurring organohalogen compounds--a comprehensive survey.

Authors:  G W Gribble
Journal:  Fortschr Chem Org Naturst       Date:  1996

5.  2-(3-Chloro-4-hydroxy-phen-yl)-N-(3,4-dimethoxy-pheneth-yl)acetamide.

Authors:  Rohan A Davis; Peter C Healy
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-05-10

6.  Structure validation in chemical crystallography.

Authors:  Anthony L Spek
Journal:  Acta Crystallogr D Biol Crystallogr       Date:  2009-01-20
  6 in total
  3 in total

1.  N-(3-Chloro-4-fluoro-phen-yl)-2-(naphthalen-1-yl)acetamide.

Authors:  A S Praveen; Jerry P Jasinski; James A Golen; B Narayana; H S Yathirajan
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-06-25

2.  N-(4-Chloro-1,3-benzothia-zol-2-yl)-2-(3-methyl-phen-yl)acetamide monohydrate.

Authors:  A S Praveen; Jerry P Jasinski; James A Golen; H S Yathirajan; B Narayana
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-09-14

3.  N-(3-Chloro-4-fluoro-phen-yl)-2,2-diphenyl-acetamide.

Authors:  A S Praveen; Jerry P Jasinski; James A Golen; B Narayana; H S Yathirajan
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-09-14
  3 in total

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