Literature DB >> 21577955

Diethyl [(5-chloro-2-hydroxy-anilino)(4-chloro-phen-yl)meth-yl]phospho-nate.

M Krishnaiah, V H H Surendra Babu, G Syam Prasad, C Suresh Reddy, Vedavati G Puranik.   

Abstract

In the title compound, C(17)H(20)Cl(2)NO(4)P, the P atom is bonded in a distorted tetra-hedral environment. The dihedral angle between the two benzene rings is 80.5 (1)°. In the crystal structure, inter-molecular O-H⋯O and N-H⋯O hydrogen bonds link pairs of mol-ecules into centrosymmetric dimers. These dimers, are in turn, linked by weak inter-molecular C-H⋯O hydrogen bonds into one-dimensional chains along [010]. Additional stabilization is provided by very weak C-H⋯Cl inter-actions.

Entities:  

Year:  2009        PMID： 21577955      PMCID： PMC2970406          DOI： 10.1107/S1600536809037039

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


Related literature

For applications of α-amino­phospho­nates, see: Allen et al. (1989 ▶); Baylis et al. (1984 ▶); Fields (1999 ▶); Hirschmann et al. (1994 ▶); Kafarski & Lejczak (1991 ▶); Miliszkiewicz et al. (1992 ▶). For the anti­bacterial activity of the title compound, see: Syam Prasad et al. (2007 ▶). For related structures, see: Boehlow et al. (1997 ▶); Yang et al. (2005 ▶); Sawka-Dobrowolska & Kowalik (1985 ▶); Sawka-Dobrowolska & Rułko (1987 ▶); Sanders et al. (1996 ▶); Ezra & Collin (1973 ▶). For P—C bond lengths in related structures, see: Rużić-Toroš et al. (1978 ▶).

Experimental

Crystal data

C17H20Cl2NO4P M = 404.21 Triclinic, a = 7.790 (3) Å b = 9.297 (4) Å c = 14.372 (6) Å α = 82.817 (6)° β = 80.842 (6)° γ = 70.323 (6)° V = 964.7 (7) Å3 Z = 2 Mo Kα radiation μ = 0.44 mm−1 T = 294 K 0.25 × 0.25 × 0.13 mm

Data collection

Siemens SMART CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.896, T max = 0.944 10997 measured reflections 4863 independent reflections 3635 reflections with I > 2σ(I) R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.053 wR(F 2) = 0.159 S = 1.05 4863 reflections 226 parameters H-atom parameters constrained Δρmax = 0.56 e Å−3 Δρmin = −0.34 e Å−3 Data collection: SMART (Bruker 2001 ▶); cell refinement: SAINT (Bruker 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ZORTEPII (Zsolnai, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: enCIFer (Allen et al., 2004 ▶) and PARST (Nardelli, 1995 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809037039/lh2891sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809037039/lh2891Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C17H20Cl2NO4PZ = 2
Mr = 404.21F(000) = 420
Triclinic, P1Dx = 1.391 Mg m−3Dm = 1.390 Mg m−3Dm measured by not measured
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.790 (3) ÅCell parameters from 4863 reflections
b = 9.297 (4) Åθ = 2.3–28.4°
c = 14.372 (6) ŵ = 0.44 mm−1
α = 82.817 (6)°T = 294 K
β = 80.842 (6)°Prism, colorless
γ = 70.323 (6)°0.25 × 0.25 × 0.13 mm
V = 964.7 (7) Å3
Siemens SMART CCD area-detector diffractometer4863 independent reflections
Radiation source: fine-focus sealed tube3635 reflections with I > 2σ(I)
graphiteRint = 0.017
ω scansθmax = 28.4°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −10→10
Tmin = 0.896, Tmax = 0.944k = −12→12
10997 measured reflectionsl = −19→19
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.159H-atom parameters constrained
S = 1.05w = 1/[σ2(Fo2) + (0.0937P)2 + 0.273P] where P = (Fo2 + 2Fc2)/3
4863 reflections(Δ/σ)max < 0.001
226 parametersΔρmax = 0.56 e Å−3
0 restraintsΔρmin = −0.34 e Å−3
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
P10.39158 (8)0.81933 (6)0.17033 (4)0.05033 (18)
Cl30.76222 (12)0.10544 (8)0.42621 (5)0.0856 (3)
Cl2−0.32728 (10)0.63628 (13)0.43963 (6)0.0973 (3)
O80.6784 (2)0.33466 (17)0.03123 (10)0.0610 (4)
H80.74020.2713−0.00610.092*
C150.4115 (3)0.6327 (2)0.23264 (13)0.0462 (4)
H150.49460.61670.28030.055*
O50.2676 (2)0.86066 (17)0.09700 (11)0.0619 (4)
C160.2269 (3)0.6284 (2)0.28494 (13)0.0449 (4)
N40.4997 (3)0.51803 (19)0.16550 (12)0.0555 (5)
H40.48460.54130.10690.067*
C100.6279 (3)0.3174 (2)0.28709 (14)0.0506 (5)
H100.56520.38000.33560.061*
C140.7033 (3)0.2733 (2)0.12175 (14)0.0474 (4)
O70.5926 (3)0.8172 (2)0.13357 (14)0.0790 (5)
C90.6079 (2)0.3719 (2)0.19319 (14)0.0435 (4)
O60.3313 (3)0.92357 (18)0.25403 (11)0.0662 (5)
C110.7415 (3)0.1695 (2)0.30794 (15)0.0550 (5)
C130.8153 (3)0.1274 (3)0.14481 (17)0.0600 (6)
H130.87830.06370.09690.072*
C120.8360 (3)0.0736 (3)0.23795 (18)0.0634 (6)
H120.9121−0.02510.25290.076*
C210.1714 (3)0.6774 (3)0.37545 (15)0.0567 (5)
H210.24950.70880.40480.068*
C19−0.1119 (3)0.6310 (3)0.38023 (17)0.0622 (6)
C200.0014 (3)0.6800 (3)0.42263 (16)0.0646 (6)
H20−0.03570.71500.48280.078*
C170.1099 (3)0.5794 (3)0.24381 (17)0.0646 (6)
H170.14600.54480.18350.078*
C18−0.0595 (4)0.5810 (4)0.2904 (2)0.0754 (7)
H18−0.13760.54870.26160.091*
C220.3166 (5)1.0826 (3)0.2469 (2)0.0840 (9)
H22A0.22711.14030.20480.101*
H22B0.43431.09450.22090.101*
C240.6719 (5)0.8128 (4)0.0351 (2)0.0952 (10)
H24A0.58900.7947−0.00230.114*
H24B0.68720.91100.01240.114*
C230.2602 (5)1.1411 (4)0.3403 (2)0.0903 (10)
H23A0.24941.24770.33530.135*
H23B0.35041.08500.38130.135*
H23C0.14371.12920.36570.135*
C250.8425 (6)0.6970 (6)0.0239 (3)0.148 (2)
H25A0.89220.6963−0.04170.222*
H25B0.82710.59960.04550.222*
H25C0.92520.71580.06010.222*
U11U22U33U12U13U23
P10.0602 (3)0.0418 (3)0.0429 (3)−0.0107 (2)0.0019 (2)−0.0079 (2)
Cl30.1068 (6)0.0725 (4)0.0536 (4)0.0006 (4)−0.0165 (3)0.0075 (3)
Cl20.0603 (4)0.1562 (8)0.0703 (5)−0.0335 (4)0.0017 (3)−0.0068 (5)
O80.0729 (10)0.0504 (8)0.0449 (8)0.0014 (7)−0.0067 (7)−0.0104 (6)
C150.0516 (10)0.0384 (9)0.0407 (9)−0.0028 (8)−0.0057 (8)−0.0070 (7)
O50.0798 (11)0.0474 (8)0.0463 (8)−0.0043 (7)−0.0086 (7)−0.0038 (6)
C160.0524 (10)0.0355 (8)0.0401 (9)−0.0045 (7)−0.0078 (8)−0.0038 (7)
N40.0666 (11)0.0432 (9)0.0396 (8)0.0062 (8)−0.0066 (8)−0.0081 (7)
C100.0520 (11)0.0473 (10)0.0449 (10)−0.0069 (8)−0.0017 (8)−0.0071 (8)
C140.0460 (10)0.0457 (10)0.0455 (10)−0.0072 (8)−0.0037 (8)−0.0088 (8)
O70.0733 (11)0.0911 (13)0.0722 (12)−0.0324 (10)0.0114 (9)−0.0145 (10)
C90.0404 (9)0.0386 (9)0.0463 (10)−0.0062 (7)−0.0030 (7)−0.0062 (7)
O60.0935 (12)0.0494 (8)0.0552 (9)−0.0257 (8)0.0070 (8)−0.0162 (7)
C110.0576 (12)0.0496 (11)0.0498 (11)−0.0071 (9)−0.0092 (9)−0.0002 (9)
C130.0604 (12)0.0482 (11)0.0565 (12)0.0038 (9)−0.0036 (10)−0.0140 (9)
C120.0623 (13)0.0452 (11)0.0655 (14)0.0060 (9)−0.0101 (11)−0.0042 (10)
C210.0623 (13)0.0642 (13)0.0442 (11)−0.0187 (10)−0.0053 (9)−0.0129 (9)
C190.0513 (11)0.0742 (15)0.0531 (12)−0.0124 (10)−0.0051 (9)0.0004 (11)
C200.0677 (14)0.0764 (15)0.0436 (11)−0.0162 (12)0.0013 (10)−0.0124 (10)
C170.0645 (13)0.0807 (16)0.0500 (12)−0.0205 (12)−0.0052 (10)−0.0212 (11)
C180.0658 (15)0.103 (2)0.0634 (15)−0.0306 (14)−0.0073 (12)−0.0221 (14)
C220.120 (2)0.0619 (15)0.0744 (17)−0.0419 (16)0.0128 (16)−0.0183 (13)
C240.084 (2)0.097 (2)0.079 (2)−0.0163 (17)0.0210 (16)0.0078 (17)
C230.119 (3)0.0762 (18)0.083 (2)−0.0425 (18)0.0148 (18)−0.0354 (15)
C250.090 (3)0.164 (4)0.123 (4)0.017 (3)0.034 (2)0.008 (3)
P1—O51.4712 (17)C13—C121.384 (3)
P1—O61.5531 (16)C13—H130.9300
P1—O71.565 (2)C12—H120.9300
P1—C151.819 (2)C21—C201.382 (3)
Cl3—C111.743 (2)C21—H210.9300
Cl2—C191.745 (3)C19—C201.367 (4)
O8—C141.370 (2)C19—C181.380 (4)
O8—H80.8200C20—H200.9300
C15—N41.447 (2)C17—C181.377 (4)
C15—C161.523 (3)C17—H170.9300
C15—H150.9800C18—H180.9300
C16—C171.381 (3)C22—C231.457 (4)
C16—C211.387 (3)C22—H22A0.9700
N4—C91.384 (2)C22—H22B0.9700
N4—H40.8600C24—C251.402 (5)
C10—C111.388 (3)C24—H24A0.9700
C10—C91.394 (3)C24—H24B0.9700
C10—H100.9300C23—H23A0.9600
C14—C131.376 (3)C23—H23B0.9600
C14—C91.407 (3)C23—H23C0.9600
O7—C241.450 (4)C25—H25A0.9600
O6—C221.436 (3)C25—H25B0.9600
C11—C121.377 (3)C25—H25C0.9600
O5—P1—O6115.79 (10)C20—C21—C16120.8 (2)
O5—P1—O7114.61 (11)C20—C21—H21119.6
O6—P1—O7104.38 (10)C16—C21—H21119.6
O5—P1—C15113.51 (10)C20—C19—C18120.8 (2)
O6—P1—C15101.05 (9)C20—C19—Cl2119.40 (19)
O7—P1—C15106.08 (11)C18—C19—Cl2119.8 (2)
C14—O8—H8109.5C19—C20—C21119.6 (2)
N4—C15—C16115.71 (17)C19—C20—H20120.2
N4—C15—P1107.67 (14)C21—C20—H20120.2
C16—C15—P1111.24 (12)C18—C17—C16121.3 (2)
N4—C15—H15107.3C18—C17—H17119.4
C16—C15—H15107.3C16—C17—H17119.4
P1—C15—H15107.3C17—C18—C19119.2 (2)
C17—C16—C21118.4 (2)C17—C18—H18120.4
C17—C16—C15121.66 (18)C19—C18—H18120.4
C21—C16—C15119.92 (18)O6—C22—C23109.6 (2)
C9—N4—C15121.70 (16)O6—C22—H22A109.8
C9—N4—H4119.1C23—C22—H22A109.8
C15—N4—H4119.1O6—C22—H22B109.8
C11—C10—C9119.82 (18)C23—C22—H22B109.8
C11—C10—H10120.1H22A—C22—H22B108.2
C9—C10—H10120.1C25—C24—O7111.0 (3)
O8—C14—C13124.40 (18)C25—C24—H24A109.4
O8—C14—C9115.33 (17)O7—C24—H24A109.4
C13—C14—C9120.25 (19)C25—C24—H24B109.4
C24—O7—P1124.7 (2)O7—C24—H24B109.4
N4—C9—C10123.96 (17)H24A—C24—H24B108.0
N4—C9—C14117.57 (17)C22—C23—H23A109.5
C10—C9—C14118.47 (17)C22—C23—H23B109.5
C22—O6—P1125.27 (17)H23A—C23—H23B109.5
C12—C11—C10121.7 (2)C22—C23—H23C109.5
C12—C11—Cl3119.93 (17)H23A—C23—H23C109.5
C10—C11—Cl3118.42 (17)H23B—C23—H23C109.5
C14—C13—C12121.27 (19)C24—C25—H25A109.5
C14—C13—H13119.4C24—C25—H25B109.5
C12—C13—H13119.4H25A—C25—H25B109.5
C11—C12—C13118.53 (19)C24—C25—H25C109.5
C11—C12—H12120.7H25A—C25—H25C109.5
C13—C12—H12120.7H25B—C25—H25C109.5
O5—P1—C15—N465.76 (17)O5—P1—O6—C22−65.0 (3)
O6—P1—C15—N4−169.61 (14)O7—P1—O6—C2262.0 (3)
O7—P1—C15—N4−60.97 (16)C15—P1—O6—C22172.0 (2)
O5—P1—C15—C16−62.00 (16)C9—C10—C11—C12−0.2 (4)
O6—P1—C15—C1662.62 (15)C9—C10—C11—Cl3−179.79 (16)
O7—P1—C15—C16171.27 (13)O8—C14—C13—C12179.0 (2)
N4—C15—C16—C17−30.9 (3)C9—C14—C13—C120.5 (4)
P1—C15—C16—C1792.4 (2)C10—C11—C12—C13−0.2 (4)
N4—C15—C16—C21150.44 (18)Cl3—C11—C12—C13179.4 (2)
P1—C15—C16—C21−86.3 (2)C14—C13—C12—C110.1 (4)
C16—C15—N4—C9−84.7 (2)C17—C16—C21—C20−1.3 (3)
P1—C15—N4—C9150.18 (17)C15—C16—C21—C20177.43 (19)
O5—P1—O7—C24−16.7 (3)C18—C19—C20—C21−1.0 (4)
O6—P1—O7—C24−144.4 (2)Cl2—C19—C20—C21−179.39 (19)
C15—P1—O7—C24109.4 (2)C16—C21—C20—C191.3 (4)
C15—N4—C9—C106.3 (3)C21—C16—C17—C181.0 (4)
C15—N4—C9—C14−173.55 (18)C15—C16—C17—C18−177.7 (2)
C11—C10—C9—N4−179.1 (2)C16—C17—C18—C19−0.7 (4)
C11—C10—C9—C140.7 (3)C20—C19—C18—C170.7 (4)
O8—C14—C9—N40.3 (3)Cl2—C19—C18—C17179.1 (2)
C13—C14—C9—N4179.0 (2)P1—O6—C22—C23−178.8 (2)
O8—C14—C9—C10−179.55 (19)P1—O7—C24—C25−130.1 (4)
C13—C14—C9—C10−0.9 (3)
D—H···AD—HH···AD···AD—H···A
N4—H4···O8i0.862.483.286 (3)157
C24—H24B···O5ii0.972.573.504 (4)162
O8—H8···O5i0.821.922.636 (2)145
C15—H15···Cl2iii0.982.913.872 (3)165
N4—H4···O80.862.282.634 (3)105
C24—H24A···O50.972.593.029 (5)107
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N4—H4⋯O8i0.862.483.286 (3)157
C24—H24B⋯O5ii0.972.573.504 (4)162
O8—H8⋯O5i0.821.922.636 (2)145
C15—H15⋯Cl2iii0.982.913.872 (3)165
N4—H4⋯O80.862.282.634 (3)105

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

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1.  Diethyl [(4-bromo-phen-yl)(5-chloro-2-hydroxy-anilino)meth-yl]phospho-nate.

Authors:  V H H Surendra Babu; M Krishnaiah; G Syam Prasad; Rajni Kant
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-10-28
  1 in total

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