Literature DB >> 22412760

Ethyl N-(2-benzoyl-4-chloro-phen-yl)-ethane-carboximidate.

H P Sumathi, A S Dayananda, Grzegorz Dutkiewicz, H S Yathirajan, Maciej Kubicki.   

Abstract

In the title compound, C(17)H(16)ClNO(2), the N=C-O-C-C fragment is planar within 0.029 (1) Å, and makes dihedral angles of 66.71 (8) and 59.61 (8)° with the planes of the chloro-phenyl and benzoyl rings, respectively. The carbonyl C=O bond is not coplanar with either of the aromatic rings; it makes angles of 42.5 and 23.5° with the normals to the ring planes. In the crystal, very weak C-H⋯O, C-H⋯Cl, C-H⋯π and π-π [inter-planar distance = 3.53 (1) Å] inter-actions are observed.

Entities:  

Year:  2012        PMID： 22412760      PMCID： PMC3297957          DOI： 10.1107/S1600536812007763

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


Related literature

For background to the medical applications of benzophenones, see, for instance: Evans et al. (1987 ▶); Revesz et al. (2004 ▶); Wiesner et al. (2002 ▶); Zeng et al. (2010 ▶). A similar structure has been described by Derieg et al. (1970 ▶)

Experimental

Crystal data

C17H16ClNO2 M = 301.76 Triclinic, a = 7.9674 (11) Å b = 8.6993 (17) Å c = 11.596 (2) Å α = 104.499 (17)° β = 94.871 (14)° γ = 95.001 (14)° V = 770.4 (2) Å3 Z = 2 Mo Kα radiation μ = 0.25 mm−1 T = 295 K 0.35 × 0.2 × 0.15 mm

Data collection

Agilent Xcalibur Eos diffractometer Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.991, T max = 1.000 13278 measured reflections 3377 independent reflections 2455 reflections with I > 2σ(I) R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.044 wR(F 2) = 0.117 S = 1.05 3377 reflections 192 parameters H-atom parameters constrained Δρmax = 0.20 e Å−3 Δρmin = −0.21 e Å−3 Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97. Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812007763/nk2143sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812007763/nk2143Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536812007763/nk2143Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C17H16ClNO2Z = 2
Mr = 301.76F(000) = 316
Triclinic, P1Dx = 1.301 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.7107 Å
a = 7.9674 (11) ÅCell parameters from 1885 reflections
b = 8.6993 (17) Åθ = 2.9–27.8°
c = 11.596 (2) ŵ = 0.25 mm−1
α = 104.499 (17)°T = 295 K
β = 94.871 (14)°Block, colourless
γ = 95.001 (14)°0.35 × 0.2 × 0.15 mm
V = 770.4 (2) Å3
Agilent Xcalibur Eos diffractometer3377 independent reflections
Radiation source: Enhance (Mo) X-ray Source2455 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
Detector resolution: 16.1544 pixels mm-1θmax = 28.2°, θmin = 3.0°
ω–scanh = −10→10
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)k = −11→11
Tmin = 0.991, Tmax = 1.000l = −15→15
13278 measured reflections
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117H-atom parameters constrained
S = 1.05w = 1/[σ2(Fo2) + (0.0479P)2 + 0.1642P] where P = (Fo2 + 2Fc2)/3
3377 reflections(Δ/σ)max = 0.001
192 parametersΔρmax = 0.20 e Å−3
0 restraintsΔρmin = −0.21 e Å−3
Experimental. Address for R L Fine Chemicals:No 15, R L Fine Chem, KHB Industrial Area, Yelahanka New Town, Bengaluru-560 106, India. Website: http://www.rlfinechem.com
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.
xyzUiso*/Ueq
C10.7628 (2)0.41768 (19)0.70454 (14)0.0376 (4)
C20.6659 (2)0.33697 (19)0.77071 (14)0.0361 (4)
C30.5286 (2)0.4041 (2)0.82141 (15)0.0411 (4)
H30.46010.34840.86190.049*
C40.4940 (2)0.5531 (2)0.81170 (15)0.0422 (4)
Cl40.32629 (7)0.63863 (7)0.87998 (5)0.0670 (2)
C50.5910 (2)0.6367 (2)0.74955 (16)0.0464 (4)
H50.56710.73740.74390.056*
C60.7238 (2)0.5683 (2)0.69612 (16)0.0463 (4)
H60.78900.62360.65350.056*
N110.90172 (18)0.34957 (17)0.65447 (13)0.0428 (4)
C120.9091 (2)0.3070 (2)0.54356 (16)0.0432 (4)
C130.7813 (3)0.3131 (3)0.44432 (18)0.0663 (6)
H13A0.68190.35280.47680.099*
H13B0.75170.20770.39230.099*
H13C0.82780.38280.39970.099*
O141.04660 (16)0.24308 (16)0.50072 (10)0.0514 (3)
C151.1748 (3)0.2175 (3)0.58734 (18)0.0611 (6)
H15A1.12480.15280.63530.073*
H15B1.22420.31910.64040.073*
C161.3068 (3)0.1356 (3)0.5231 (2)0.0828 (8)
H16A1.25580.03870.46680.124*
H16B1.38850.11070.57940.124*
H16C1.36210.20400.48100.124*
C210.7012 (2)0.1754 (2)0.78588 (15)0.0398 (4)
O220.58787 (18)0.06586 (16)0.76157 (14)0.0632 (4)
C230.8739 (2)0.15418 (19)0.83424 (14)0.0368 (4)
C240.9812 (2)0.2816 (2)0.90603 (16)0.0455 (4)
H240.94790.38400.92170.055*
C251.1373 (3)0.2576 (3)0.95454 (18)0.0587 (5)
H251.20780.34321.00490.070*
C261.1892 (3)0.1075 (3)0.9288 (2)0.0655 (6)
H261.29510.09170.96130.079*
C271.0850 (3)−0.0190 (3)0.8554 (2)0.0672 (6)
H271.1214−0.12020.83650.081*
C280.9271 (3)0.0033 (2)0.80965 (18)0.0533 (5)
H280.8554−0.08350.76190.064*
U11U22U33U12U13U23
C10.0369 (9)0.0398 (9)0.0377 (9)0.0072 (7)0.0026 (7)0.0122 (7)
C20.0353 (9)0.0371 (8)0.0365 (8)0.0070 (7)0.0002 (7)0.0111 (7)
C30.0375 (9)0.0466 (10)0.0428 (9)0.0092 (8)0.0051 (8)0.0165 (8)
C40.0411 (10)0.0466 (10)0.0420 (9)0.0175 (8)0.0043 (8)0.0133 (8)
Cl40.0666 (4)0.0787 (4)0.0720 (4)0.0447 (3)0.0256 (3)0.0314 (3)
C50.0540 (11)0.0403 (9)0.0498 (10)0.0164 (9)0.0026 (9)0.0181 (8)
C60.0505 (11)0.0437 (10)0.0520 (10)0.0090 (9)0.0088 (9)0.0235 (8)
N110.0417 (8)0.0502 (9)0.0418 (8)0.0141 (7)0.0086 (7)0.0174 (7)
C120.0384 (10)0.0510 (10)0.0443 (10)0.0086 (8)0.0075 (8)0.0175 (8)
C130.0553 (13)0.0958 (17)0.0489 (11)0.0261 (12)0.0009 (10)0.0165 (11)
O140.0427 (7)0.0750 (9)0.0404 (7)0.0197 (7)0.0082 (6)0.0165 (6)
C150.0527 (12)0.0842 (15)0.0502 (11)0.0284 (11)0.0031 (10)0.0184 (10)
C160.0640 (15)0.118 (2)0.0739 (15)0.0435 (15)0.0100 (13)0.0262 (15)
C210.0429 (10)0.0360 (9)0.0418 (9)0.0070 (8)0.0063 (8)0.0112 (7)
O220.0490 (8)0.0447 (7)0.0956 (11)−0.0023 (7)−0.0048 (8)0.0242 (7)
C230.0421 (10)0.0353 (8)0.0375 (9)0.0108 (7)0.0074 (7)0.0145 (7)
C240.0478 (11)0.0410 (9)0.0480 (10)0.0105 (8)0.0025 (9)0.0114 (8)
C250.0486 (12)0.0701 (14)0.0584 (12)0.0067 (10)−0.0065 (10)0.0223 (10)
C260.0476 (12)0.0906 (17)0.0721 (14)0.0281 (12)0.0055 (11)0.0404 (13)
C270.0729 (15)0.0616 (13)0.0798 (15)0.0405 (13)0.0148 (13)0.0286 (12)
C280.0621 (13)0.0387 (10)0.0623 (12)0.0166 (9)0.0062 (10)0.0154 (9)
C1—C21.398 (2)C15—C161.472 (3)
C1—C61.398 (2)C15—H15A0.9700
C1—N111.402 (2)C15—H15B0.9700
C2—C31.390 (2)C16—H16A0.9600
C2—C211.506 (2)C16—H16B0.9600
C3—C41.379 (2)C16—H16C0.9600
C3—H30.9300C21—O221.214 (2)
C4—C51.380 (3)C21—C231.486 (2)
C4—Cl41.7391 (17)C23—C241.380 (2)
C5—C61.376 (2)C23—C281.383 (2)
C5—H50.9300C24—C251.375 (3)
C6—H60.9300C24—H240.9300
N11—C121.254 (2)C25—C261.373 (3)
C12—O141.348 (2)C25—H250.9300
C12—C131.485 (3)C26—C271.370 (3)
C13—H13A0.9600C26—H260.9300
C13—H13B0.9600C27—C281.372 (3)
C13—H13C0.9600C27—H270.9300
O14—C151.442 (2)C28—H280.9300
C2—C1—C6118.80 (15)C16—C15—H15A109.9
C2—C1—N11119.15 (14)O14—C15—H15B109.9
C6—C1—N11121.95 (16)C16—C15—H15B109.9
C3—C2—C1119.58 (15)H15A—C15—H15B108.3
C3—C2—C21118.18 (15)C15—C16—H16A109.5
C1—C2—C21122.20 (15)C15—C16—H16B109.5
C4—C3—C2120.03 (16)H16A—C16—H16B109.5
C4—C3—H3120.0C15—C16—H16C109.5
C2—C3—H3120.0H16A—C16—H16C109.5
C3—C4—C5121.20 (16)H16B—C16—H16C109.5
C3—C4—Cl4119.55 (14)O22—C21—C23120.95 (16)
C5—C4—Cl4119.25 (13)O22—C21—C2119.91 (16)
C6—C5—C4118.86 (16)C23—C21—C2119.12 (15)
C6—C5—H5120.6C24—C23—C28119.14 (17)
C4—C5—H5120.6C24—C23—C21121.28 (15)
C5—C6—C1121.44 (17)C28—C23—C21119.57 (16)
C5—C6—H6119.3C25—C24—C23120.16 (17)
C1—C6—H6119.3C25—C24—H24119.9
C12—N11—C1122.68 (15)C23—C24—H24119.9
N11—C12—O14119.97 (16)C26—C25—C24120.2 (2)
N11—C12—C13129.03 (17)C26—C25—H25119.9
O14—C12—C13110.99 (15)C24—C25—H25119.9
C12—C13—H13A109.5C27—C26—C25120.0 (2)
C12—C13—H13B109.5C27—C26—H26120.0
H13A—C13—H13B109.5C25—C26—H26120.0
C12—C13—H13C109.5C26—C27—C28120.08 (19)
H13A—C13—H13C109.5C26—C27—H27120.0
H13B—C13—H13C109.5C28—C27—H27120.0
C12—O14—C15116.82 (14)C27—C28—C23120.4 (2)
O14—C15—C16108.70 (17)C27—C28—H28119.8
O14—C15—H15A109.9C23—C28—H28119.8
C6—C1—C2—C33.2 (2)C13—C12—O14—C15−174.91 (18)
N11—C1—C2—C3179.56 (15)C12—O14—C15—C16175.44 (19)
C6—C1—C2—C21−179.05 (16)C3—C2—C21—O2250.6 (2)
N11—C1—C2—C21−2.6 (2)C1—C2—C21—O22−127.22 (19)
C1—C2—C3—C4−3.4 (2)C3—C2—C21—C23−127.49 (17)
C21—C2—C3—C4178.69 (16)C1—C2—C21—C2354.7 (2)
C2—C3—C4—C51.7 (3)O22—C21—C23—C24−153.15 (17)
C2—C3—C4—Cl4−177.78 (13)C2—C21—C23—C2424.9 (2)
C3—C4—C5—C60.4 (3)O22—C21—C23—C2825.1 (3)
Cl4—C4—C5—C6179.81 (14)C2—C21—C23—C28−156.77 (16)
C4—C5—C6—C1−0.6 (3)C28—C23—C24—C25−1.5 (3)
C2—C1—C6—C5−1.2 (3)C21—C23—C24—C25176.78 (17)
N11—C1—C6—C5−177.46 (16)C23—C24—C25—C262.0 (3)
C2—C1—N11—C12116.53 (19)C24—C25—C26—C27−0.5 (3)
C6—C1—N11—C12−67.2 (2)C25—C26—C27—C28−1.5 (3)
C1—N11—C12—O14179.59 (15)C26—C27—C28—C232.0 (3)
C1—N11—C12—C13−1.7 (3)C24—C23—C28—C27−0.5 (3)
N11—C12—O14—C154.1 (3)C21—C23—C28—C27−178.80 (18)
D—H···AD—HH···AD···AD—H···A
C5—H5···O22i0.932.803.704 (2)164
C6—H6···O14ii0.932.733.648 (2)172
C16—H16B···O22iii0.962.663.614 (3)171
C27—H27···Cl4iv0.932.883.739 (2)154
C25—H25···CgAv0.932.903.744 (3)151
Table 1

Hydrogen-bond geometry (Å, °)

CgA denotes the centroid of the phenyl ring C1–C6.

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C5—H5⋯O22i0.932.803.704 (2)164
C6—H6⋯O14ii0.932.733.648 (2)172
C16—H16B⋯O22iii0.962.663.614 (3)171
C27—H27⋯Cl4iv0.932.883.739 (2)154
C25—H25⋯CgAv0.932.903.744 (3)151

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

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