Literature DB >> 22091027

2,2-Diphenyl-acetamide.

Jerry P Jasinski, James A Golen, M S Siddegowda, H S Yathirajan, M T Swamy.   

Abstract

In the title compound, C(14)H(13)NO, which has two mol-ecules in the asymmetric unit, the dihedral angles between the mean planes of the benzene rings are 84.6 (7) and 85.0 (6)°. N-H⋯O hydrogen bonds [forming R(2) (2)(8) ring motifs] and C-H⋯O hydrogen bonds dominate the crystal packing, forming zigzag chains parallel to the a axis. In addition, weak inter-molecular C-H⋯π inter-actions are observed.

Entities:  

Year:  2011        PMID: 22091027      PMCID: PMC3213448          DOI: 10.1107/S1600536811026717

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


Related literature

For the synthesis and anti­mycobacterial activity of 2,2-diphenyl­acetamide derivatives, see: Guzel et al. (2006 ▶). For related structures, see: Akkurt et al. (2007 ▶); Dutkiewicz et al. (2010 ▶); Gerkin (1998 ▶); Krigbaum et al. (1968 ▶); Narasegowda et al. (2005 ▶); Yathirajan et al. (2005 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C14H13NO M = 211.25 Monoclinic, a = 5.1687 (3) Å b = 28.5511 (13) Å c = 7.8006 (4) Å β = 98.152 (5)° V = 1139.52 (10) Å3 Z = 4 Cu Kα radiation μ = 0.61 mm−1 T = 173 K 0.40 × 0.25 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur Eos Gemini diffractometer Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010 ▶) T min = 0.792, T max = 0.887 6490 measured reflections 3978 independent reflections 3869 reflections with I > 2σ(I) R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.037 wR(F 2) = 0.107 S = 1.07 3978 reflections 303 parameters 9 restraints H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.21 e Å−3 Δρmin = −0.20 e Å−3 Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2010 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL. Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811026717/jh2307sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811026717/jh2307Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536811026717/jh2307Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C14H13NOF(000) = 448
Mr = 211.25Dx = 1.231 Mg m3
Monoclinic, P21Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2ybCell parameters from 5082 reflections
a = 5.1687 (3) Åθ = 4.6–70.4°
b = 28.5511 (13) ŵ = 0.61 mm1
c = 7.8006 (4) ÅT = 173 K
β = 98.152 (5)°Block, colorless
V = 1139.52 (10) Å30.40 × 0.25 × 0.20 mm
Z = 4
Oxford Diffraction Xcalibur Eos Gemini diffractometer3978 independent reflections
Radiation source: Enhance (Cu) X-ray Source3869 reflections with I > 2σ(I)
graphiteRint = 0.017
Detector resolution: 16.1500 pixels mm-1θmax = 70.5°, θmin = 5.7°
ω scansh = −6→6
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)k = −34→34
Tmin = 0.792, Tmax = 0.887l = −9→8
6490 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)] = 0.037H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.107w = 1/[σ2(Fo2) + (0.0695P)2 + 0.1057P] where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.027
3978 reflectionsΔρmax = 0.21 e Å3
303 parametersΔρmin = −0.20 e Å3
9 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0118 (13)
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
N10.9797 (3)0.54261 (6)0.6365 (2)0.0459 (3)
H1B1.121 (3)0.5307 (8)0.600 (3)0.055*
H1A0.984 (5)0.5667 (6)0.706 (3)0.055*
O21.0081 (2)0.62240 (4)−0.11977 (17)0.0465 (3)
O10.5496 (2)0.53784 (5)0.64407 (16)0.0459 (3)
N20.5779 (3)0.61736 (6)−0.1120 (2)0.0469 (4)
H2B0.561 (5)0.5935 (6)−0.185 (3)0.056*
H2A0.431 (3)0.6281 (9)−0.080 (3)0.056*
C10.7494 (3)0.52226 (5)0.5965 (2)0.0359 (3)
C20.7440 (3)0.47718 (6)0.4902 (2)0.0377 (3)
H2C0.90970.47580.43810.045*
C30.5167 (3)0.47744 (6)0.3416 (2)0.0406 (4)
C40.4550 (5)0.51789 (8)0.2469 (3)0.0678 (6)
H4A0.55340.54560.27590.081*
C50.2520 (6)0.51860 (10)0.1106 (4)0.0824 (8)
H5A0.21300.54670.04690.099*
C60.1062 (5)0.47893 (10)0.0666 (3)0.0683 (6)
H6A−0.03530.4796−0.02540.082*
C70.1684 (4)0.43851 (9)0.1575 (3)0.0577 (5)
H7A0.07070.41080.12720.069*
C80.3724 (4)0.43764 (7)0.2933 (2)0.0461 (4)
H8A0.41380.40920.35430.055*
C90.7419 (3)0.43519 (5)0.6105 (2)0.0375 (3)
C100.5760 (4)0.43225 (7)0.7334 (3)0.0518 (4)
H10A0.45770.45710.74510.062*
C110.5795 (5)0.39352 (9)0.8402 (3)0.0606 (5)
H11A0.46300.39210.92390.073*
C120.7488 (5)0.35715 (8)0.8270 (3)0.0607 (5)
H12A0.75210.33090.90200.073*
C130.9135 (5)0.35925 (9)0.7036 (4)0.0738 (7)
H13A1.02880.33400.69100.089*
C140.9117 (4)0.39807 (8)0.5981 (3)0.0607 (5)
H14A1.02940.39940.51510.073*
C150.8083 (3)0.63780 (6)−0.0712 (2)0.0355 (3)
C160.8143 (3)0.68289 (5)0.0360 (2)0.0367 (3)
H16A0.64950.68410.08920.044*
C170.8148 (3)0.72535 (6)−0.0840 (2)0.0373 (3)
C180.9825 (4)0.72830 (7)−0.2076 (2)0.0505 (4)
H18A1.10050.7034−0.22010.061*
C190.9779 (4)0.76758 (8)−0.3129 (3)0.0594 (5)
H19A1.09410.7694−0.39670.071*
C200.8089 (5)0.80352 (7)−0.2976 (3)0.0585 (5)
H20A0.80610.8301−0.37100.070*
C210.6427 (5)0.80100 (8)−0.1751 (3)0.0654 (6)
H21A0.52570.8260−0.16270.078*
C220.6461 (4)0.76191 (7)−0.0699 (3)0.0533 (5)
H22A0.52940.76030.01370.064*
C231.0422 (3)0.68233 (6)0.1827 (2)0.0404 (3)
C241.1076 (5)0.64165 (8)0.2764 (3)0.0702 (6)
H24A1.01190.61370.24620.084*
C251.3098 (6)0.64110 (11)0.4128 (3)0.0848 (8)
H25A1.35080.61290.47570.102*
C261.4513 (5)0.68078 (11)0.4580 (3)0.0696 (6)
H26A1.59220.68010.55050.084*
C271.3884 (4)0.72136 (9)0.3690 (3)0.0608 (5)
H27A1.48470.74910.40080.073*
C281.1853 (4)0.72226 (7)0.2329 (2)0.0468 (4)
H28A1.14320.75080.17270.056*
U11U22U33U12U13U23
N10.0328 (6)0.0411 (8)0.0651 (9)−0.0033 (6)0.0110 (6)−0.0140 (7)
O20.0316 (5)0.0435 (7)0.0654 (7)−0.0009 (5)0.0106 (5)−0.0159 (5)
O10.0321 (5)0.0424 (6)0.0639 (7)−0.0001 (5)0.0093 (5)−0.0150 (6)
N20.0325 (6)0.0435 (8)0.0652 (9)−0.0021 (6)0.0086 (6)−0.0147 (7)
C10.0322 (7)0.0325 (8)0.0430 (8)0.0009 (5)0.0051 (6)−0.0007 (6)
C20.0361 (7)0.0352 (8)0.0436 (8)−0.0012 (6)0.0116 (6)−0.0032 (7)
C30.0436 (8)0.0388 (9)0.0407 (8)−0.0019 (6)0.0107 (6)−0.0039 (7)
C40.0871 (15)0.0441 (11)0.0663 (13)−0.0108 (10)−0.0092 (11)0.0077 (9)
C50.107 (2)0.0650 (15)0.0660 (14)−0.0016 (14)−0.0202 (14)0.0137 (12)
C60.0713 (13)0.0847 (16)0.0442 (10)0.0011 (12)−0.0085 (9)−0.0065 (10)
C70.0624 (11)0.0665 (13)0.0438 (9)−0.0133 (10)0.0061 (8)−0.0125 (9)
C80.0545 (9)0.0452 (10)0.0398 (8)−0.0061 (8)0.0109 (7)−0.0068 (7)
C90.0368 (7)0.0332 (8)0.0423 (8)−0.0013 (6)0.0048 (6)−0.0052 (6)
C100.0547 (10)0.0487 (11)0.0557 (10)0.0113 (8)0.0204 (8)0.0036 (8)
C110.0734 (13)0.0576 (11)0.0565 (11)0.0015 (10)0.0284 (10)0.0067 (10)
C120.0769 (13)0.0434 (11)0.0636 (12)0.0004 (10)0.0164 (10)0.0106 (9)
C130.0837 (15)0.0440 (11)0.1012 (18)0.0193 (11)0.0389 (14)0.0163 (11)
C140.0657 (12)0.0439 (10)0.0795 (14)0.0133 (9)0.0346 (10)0.0054 (10)
C150.0327 (7)0.0324 (7)0.0418 (7)−0.0002 (6)0.0066 (6)−0.0006 (6)
C160.0357 (7)0.0337 (8)0.0430 (8)−0.0020 (6)0.0129 (6)−0.0041 (7)
C170.0363 (7)0.0358 (8)0.0399 (7)−0.0021 (6)0.0055 (6)−0.0057 (6)
C180.0531 (10)0.0481 (10)0.0534 (10)0.0080 (8)0.0186 (8)0.0042 (8)
C190.0686 (12)0.0591 (12)0.0550 (11)0.0016 (10)0.0245 (9)0.0069 (10)
C200.0752 (13)0.0429 (11)0.0583 (11)−0.0010 (9)0.0123 (10)0.0104 (8)
C210.0786 (15)0.0409 (10)0.0818 (15)0.0171 (9)0.0294 (12)0.0066 (10)
C220.0597 (10)0.0404 (9)0.0655 (11)0.0073 (8)0.0291 (9)0.0050 (8)
C230.0451 (8)0.0399 (9)0.0381 (7)−0.0005 (6)0.0123 (6)−0.0036 (7)
C240.0878 (16)0.0478 (12)0.0684 (13)−0.0088 (11)−0.0116 (12)0.0077 (10)
C250.109 (2)0.0685 (16)0.0669 (14)0.0064 (15)−0.0228 (14)0.0127 (12)
C260.0741 (13)0.0856 (16)0.0441 (10)0.0001 (12)−0.0091 (9)−0.0043 (11)
C270.0643 (12)0.0720 (14)0.0462 (9)−0.0175 (10)0.0081 (9)−0.0141 (10)
C280.0553 (10)0.0452 (10)0.0411 (8)−0.0090 (8)0.0112 (7)−0.0057 (7)
N1—C11.322 (2)C12—H12A0.9500
N1—H1B0.889 (13)C13—C141.380 (3)
N1—H1A0.873 (13)C13—H13A0.9500
O2—C151.2306 (19)C14—H14A0.9500
O1—C11.2292 (19)C15—C161.533 (2)
N2—C151.324 (2)C16—C231.521 (2)
N2—H2B0.883 (13)C16—C171.532 (2)
N2—H2A0.889 (13)C16—H16A1.0000
C1—C21.529 (2)C17—C221.375 (2)
C2—C91.523 (2)C17—C181.387 (2)
C2—C31.529 (2)C18—C191.388 (3)
C2—H2C1.0000C18—H18A0.9500
C3—C81.382 (2)C19—C201.364 (3)
C3—C41.384 (3)C19—H19A0.9500
C4—C51.384 (3)C20—C211.374 (4)
C4—H4A0.9500C20—H20A0.9500
C5—C61.377 (4)C21—C221.384 (3)
C5—H5A0.9500C21—H21A0.9500
C6—C71.369 (4)C22—H22A0.9500
C6—H6A0.9500C23—C281.385 (2)
C7—C81.385 (3)C23—C241.389 (3)
C7—H7A0.9500C24—C251.382 (3)
C8—H8A0.9500C24—H24A0.9500
C9—C101.377 (3)C25—C261.367 (4)
C9—C141.388 (3)C25—H25A0.9500
C10—C111.383 (3)C26—C271.366 (4)
C10—H10A0.9500C26—H26A0.9500
C11—C121.371 (3)C27—C281.384 (3)
C11—H11A0.9500C27—H27A0.9500
C12—C131.373 (4)C28—H28A0.9500
C1—N1—H1B120.8 (16)C13—C14—C9121.52 (19)
C1—N1—H1A115.9 (16)C13—C14—H14A119.2
H1B—N1—H1A123 (2)C9—C14—H14A119.2
C15—N2—H2B119.8 (16)O2—C15—N2122.28 (16)
C15—N2—H2A123.8 (16)O2—C15—C16120.98 (13)
H2B—N2—H2A116 (2)N2—C15—C16116.72 (13)
O1—C1—N1122.46 (15)C23—C16—C17113.57 (13)
O1—C1—C2121.11 (14)C23—C16—C15110.82 (13)
N1—C1—C2116.42 (14)C17—C16—C15109.44 (12)
C9—C2—C1109.27 (13)C23—C16—H16A107.6
C9—C2—C3113.52 (13)C17—C16—H16A107.6
C1—C2—C3111.11 (13)C15—C16—H16A107.6
C9—C2—H2C107.6C22—C17—C18118.40 (16)
C1—C2—H2C107.6C22—C17—C16119.72 (14)
C3—C2—H2C107.6C18—C17—C16121.88 (14)
C8—C3—C4117.79 (17)C17—C18—C19120.03 (18)
C8—C3—C2121.97 (15)C17—C18—H18A120.0
C4—C3—C2120.21 (16)C19—C18—H18A120.0
C5—C4—C3121.0 (2)C20—C19—C18120.89 (19)
C5—C4—H4A119.5C20—C19—H19A119.6
C3—C4—H4A119.5C18—C19—H19A119.6
C4—C5—C6120.5 (2)C19—C20—C21119.51 (19)
C4—C5—H5A119.7C19—C20—H20A120.2
C6—C5—H5A119.7C21—C20—H20A120.2
C7—C6—C5119.0 (2)C20—C21—C22119.9 (2)
C7—C6—H6A120.5C20—C21—H21A120.1
C5—C6—H6A120.5C22—C21—H21A120.1
C6—C7—C8120.59 (19)C17—C22—C21121.31 (19)
C6—C7—H7A119.7C17—C22—H22A119.3
C8—C7—H7A119.7C21—C22—H22A119.3
C3—C8—C7121.11 (18)C28—C23—C24117.35 (17)
C3—C8—H8A119.4C28—C23—C16121.97 (15)
C7—C8—H8A119.4C24—C23—C16120.64 (16)
C10—C9—C14117.65 (17)C25—C24—C23121.1 (2)
C10—C9—C2122.44 (15)C25—C24—H24A119.5
C14—C9—C2119.91 (15)C23—C24—H24A119.5
C9—C10—C11120.79 (18)C26—C25—C24120.5 (2)
C9—C10—H10A119.6C26—C25—H25A119.7
C11—C10—H10A119.6C24—C25—H25A119.7
C12—C11—C10120.97 (19)C25—C26—C27119.4 (2)
C12—C11—H11A119.5C25—C26—H26A120.3
C10—C11—H11A119.5C27—C26—H26A120.3
C11—C12—C13119.0 (2)C26—C27—C28120.4 (2)
C11—C12—H12A120.5C26—C27—H27A119.8
C13—C12—H12A120.5C28—C27—H27A119.8
C12—C13—C14120.0 (2)C27—C28—C23121.22 (18)
C12—C13—H13A120.0C27—C28—H28A119.4
C14—C13—H13A120.0C23—C28—H28A119.4
O1—C1—C2—C9−79.23 (19)O2—C15—C16—C23−46.8 (2)
N1—C1—C2—C999.42 (17)N2—C15—C16—C23135.00 (15)
O1—C1—C2—C346.8 (2)O2—C15—C16—C1779.24 (18)
N1—C1—C2—C3−134.55 (16)N2—C15—C16—C17−99.00 (16)
C9—C2—C3—C8−17.6 (2)C23—C16—C17—C22−103.20 (18)
C1—C2—C3—C8−141.21 (16)C15—C16—C17—C22132.39 (17)
C9—C2—C3—C4164.54 (19)C23—C16—C17—C1876.54 (19)
C1—C2—C3—C440.9 (2)C15—C16—C17—C18−47.87 (19)
C8—C3—C4—C51.2 (4)C22—C17—C18—C190.2 (3)
C2—C3—C4—C5179.2 (2)C16—C17—C18—C19−179.50 (18)
C3—C4—C5—C60.2 (5)C17—C18—C19—C20−0.4 (3)
C4—C5—C6—C7−1.3 (5)C18—C19—C20—C210.6 (4)
C5—C6—C7—C80.9 (4)C19—C20—C21—C22−0.7 (4)
C4—C3—C8—C7−1.6 (3)C18—C17—C22—C21−0.3 (3)
C2—C3—C8—C7−179.55 (17)C16—C17—C22—C21179.4 (2)
C6—C7—C8—C30.6 (3)C20—C21—C22—C170.6 (4)
C1—C2—C9—C1047.5 (2)C17—C16—C23—C2818.5 (2)
C3—C2—C9—C10−77.1 (2)C15—C16—C23—C28142.15 (16)
C1—C2—C9—C14−132.47 (18)C17—C16—C23—C24−164.12 (19)
C3—C2—C9—C14102.9 (2)C15—C16—C23—C24−40.5 (2)
C14—C9—C10—C11−0.1 (3)C28—C23—C24—C25−0.8 (4)
C2—C9—C10—C11179.91 (18)C16—C23—C24—C25−178.3 (2)
C9—C10—C11—C120.3 (3)C23—C24—C25—C26−0.4 (5)
C10—C11—C12—C13−1.0 (4)C24—C25—C26—C271.1 (5)
C11—C12—C13—C141.6 (4)C25—C26—C27—C28−0.8 (4)
C12—C13—C14—C9−1.4 (4)C26—C27—C28—C23−0.4 (3)
C10—C9—C14—C130.7 (3)C24—C23—C28—C271.1 (3)
C2—C9—C14—C13−179.3 (2)C16—C23—C28—C27178.60 (17)
Cg1 and Cg4 are the centroids of the C3–C8 and C23–C28 rings, respectively.
D—H···AD—HH···AD···AD—H···A
N1—H1B···O1i0.89 (1)2.20 (2)2.9409 (17)140 (2)
N1—H1A···O2ii0.87 (1)2.09 (1)2.9575 (19)177 (2)
N2—H2B···O1iii0.88 (1)2.07 (1)2.9526 (19)176 (2)
N2—H2A···O2iv0.89 (1)2.17 (2)2.9407 (18)145 (2)
N1—H1A···N2ii0.87 (1)3.06 (2)3.7246 (18)134.(2)
N2—H2B···N1iii0.88 (1)3.10 (2)3.7246 (18)130.(2)
C10—H10A···O10.952.503.093 (2)120.
C18—H18A···O20.952.513.099 (2)120
C2—H2C···Cg1i1.002.963.9379 (18)165
C16—H16A···Cg4iv1.002.953.9263 (18)166
Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg4 are the centroids of the C3–C8 and C23–C28 rings, respectively.

D—H⋯AD—HH⋯ADAD—H⋯A
N1—H1B⋯O1i0.89 (1)2.20 (2)2.9409 (17)140 (2)
N1—H1A⋯O2ii0.87 (1)2.09 (1)2.9575 (19)177 (2)
N2—H2B⋯O1iii0.88 (1)2.07 (1)2.9526 (19)176 (2)
N2—H2A⋯O2iv0.89 (1)2.17 (2)2.9407 (18)145 (2)
N1—H1A⋯N2ii0.87 (1)3.06 (2)3.7246 (18)134 (2)
N2—H2B⋯N1iii0.88 (1)3.10 (2)3.7246 (18)130 (2)
C10—H10A⋯O10.952.503.093 (2)120
C18—H18A⋯O20.952.513.099 (2)120
C2—H2CCg1i1.002.963.9379 (18)165
C16—H16ACg4iv1.002.953.9263 (18)166

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .

  3 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.  Hydrogen-bonded trimers in 4,4'-dimethylbiphenyl-2,2'-dicarboxylic acid.

Authors:  R E Gerkin
Journal:  Acta Crystallogr C       Date:  1998-12-15       Impact factor: 1.172

3.  2-Chloro-N-[4-chloro-2-(2-chloro-benzo-yl)phen-yl]acetamide.

Authors:  Grzegorz Dutkiewicz; B P Siddaraju; H S Yathirajan; B Narayana; Maciej Kubicki
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-01-30
  3 in total

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