organic compounds
Diethyl [hydroxy(2-nitrophenyl)methyl]phosphonate
aKey Laboratory of Pesticides and Chemical Biology of the Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, People's Republic of China
*Correspondence e-mail: cbbbccn@yahoo.com.cn
In the title molecule, C11H16NO6P, the nitro group is twisted out of the mean plane of the benzene ring at 29.91 (3)°. The two ethyl groups are disordered between two orientations in the ratios 0.784 (7)/0.216 (7) and 0.733 (6)/0.267 (6). Intermolecular O—H⋯O hydrogen bonds link the molecules into centrosymmetric dimers.
Experimental
Crystal data
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Data collection
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Refinement
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Data collection: SMART (Bruker, 2001); cell SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.
Supporting information
https://doi.org/10.1107/S1600536807063453/cv2361sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807063453/cv2361Isup2.hkl
To a solution of 2-nitrobenzylaldehyde(1 mmol) in tetrahydrofuran(0.6 ml) was added diphenyl phosphite(1 mmol) at 0°C. After 15 minutes, triethylamine (0.1 ml) was added, and the reaction mixture was stirred for 2 h at 0°C. The resulting solution was washed with saturated NaHCO3 solution, extracted with dichloromethane and dried over MgSO4. The solution was filtered and purified by column chroatography on silica gel, using ehtyl acetate and petroleum as eluant to afford the title compound. Crystals of (I) suitable for X-ray data collection were obtained by slow evaporation of a chloroform and methanol solution in ratio of 100:1 at 293 K.
C-bound H atoms were initially located in difference maps and then constrained to their ideal positions (C–H = 0.93–0.98 Å), and refined as riding with Uiso(H)=1.2–1.5Ueq(C). The hydroxy atom H3A was located on difference map and refined with bond restraint O–H = 0.82 (1) Å, and with the Uiso(H) =1.5Ueq(O). Two ethyl groups were treated as disordered between two orientations with the refined occupancies of 0.786 (7)/0.214 (7) [C8—C9/C8'-C9'] and 0.727 (6)/0.273 (6) [C10—C11/C10'-C11'], respectively.
Phosphonates, especially
forms, are particularly important in connection with their remarkable biological activities. They have been used as enzyme inhibitors, antibacterial agents, anti-HIV agents, botryticides, and haptens for catalytic antibodies (Allen et al., 1978; Hirschmann et al., 1994). In this regard, the preparation of various optically active phosphonates with a diversity of structures is highly desirable for drug discovery and medicinal chemistry. The title compound (I) was obtained in the reaction of diphenylphosphite with an aromatic aldehyde in the presence of triethylamine.In (I) (Fig. 1), the nitro group is twisted out of the mean plane of benzene ring at 29.91 (3)°. In the crystal (Fig. 2), intermolecular O—H···O hydrogen bonds (Table 1) link the molecules into centrosymmetric dimers (Fig. 2).
For general background, see: Allen et al. (1978); Hirschmann et al. (1994).
Data collection: SMART (Bruker, 2001); cell
SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON (Spek, 2003).C11H16NO6P | Z = 2 |
Mr = 289.22 | F(000) = 304 |
Triclinic, P1 | Dx = 1.401 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.5659 (13) Å | Cell parameters from 3014 reflections |
b = 8.3844 (15) Å | θ = 2.8–28.0° |
c = 12.557 (2) Å | µ = 0.22 mm−1 |
α = 73.356 (3)° | T = 291 K |
β = 87.391 (3)° | Block, colourless |
γ = 64.432 (3)° | 0.30 × 0.20 × 0.20 mm |
V = 685.6 (2) Å3 |
Bruker SMART 4K CCD area-detector diffractometer | 2381 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.020 |
Graphite monochromator | θmax = 26.5°, θmin = 1.7° |
φ and ω scans | h = −9→9 |
6168 measured reflections | k = −10→10 |
2800 independent reflections | l = −15→15 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.052 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.157 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0955P)2 + 0.1438P] where P = (Fo2 + 2Fc2)/3 |
2800 reflections | (Δ/σ)max < 0.001 |
193 parameters | Δρmax = 0.38 e Å−3 |
1 restraint | Δρmin = −0.20 e Å−3 |
C11H16NO6P | γ = 64.432 (3)° |
Mr = 289.22 | V = 685.6 (2) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.5659 (13) Å | Mo Kα radiation |
b = 8.3844 (15) Å | µ = 0.22 mm−1 |
c = 12.557 (2) Å | T = 291 K |
α = 73.356 (3)° | 0.30 × 0.20 × 0.20 mm |
β = 87.391 (3)° |
Bruker SMART 4K CCD area-detector diffractometer | 2381 reflections with I > 2σ(I) |
6168 measured reflections | Rint = 0.020 |
2800 independent reflections |
R[F2 > 2σ(F2)] = 0.052 | 1 restraint |
wR(F2) = 0.157 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | Δρmax = 0.38 e Å−3 |
2800 reflections | Δρmin = −0.20 e Å−3 |
193 parameters |
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 F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > σ(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
P1 | 0.33556 (9) | 0.33802 (9) | 0.13960 (4) | 0.0648 (2) | |
C1 | 0.6327 (3) | 0.2053 (3) | 0.31083 (16) | 0.0521 (4) | |
C2 | 0.5564 (3) | 0.2596 (3) | 0.40485 (16) | 0.0548 (5) | |
C3 | 0.6201 (4) | 0.1419 (3) | 0.51225 (18) | 0.0691 (6) | |
H3 | 0.5640 | 0.1819 | 0.5728 | 0.083* | |
C4 | 0.7655 (4) | −0.0332 (3) | 0.5291 (2) | 0.0760 (6) | |
H4 | 0.8103 | −0.1125 | 0.6012 | 0.091* | |
C5 | 0.8460 (4) | −0.0924 (3) | 0.4386 (2) | 0.0782 (7) | |
H5 | 0.9455 | −0.2115 | 0.4495 | 0.094* | |
C6 | 0.7784 (3) | 0.0256 (3) | 0.3323 (2) | 0.0676 (5) | |
H6 | 0.8328 | −0.0171 | 0.2723 | 0.081* | |
N1 | 0.4048 (3) | 0.4469 (3) | 0.39566 (16) | 0.0673 (5) | |
C7 | 0.5651 (3) | 0.3239 (3) | 0.19053 (16) | 0.0574 (5) | |
H7 | 0.5481 | 0.4491 | 0.1839 | 0.069* | |
C8 | 0.0059 (6) | 0.5738 (7) | 0.1961 (3) | 0.0961 (13) | 0.784 (7) |
H8A | −0.0469 | 0.6001 | 0.1208 | 0.115* | 0.784 (7) |
H8B | 0.0354 | 0.6744 | 0.1987 | 0.115* | 0.784 (7) |
C9 | −0.1387 (9) | 0.5585 (11) | 0.2750 (7) | 0.1132 (17) | 0.784 (7) |
H9A | −0.1731 | 0.4637 | 0.2688 | 0.170* | 0.784 (7) |
H9B | −0.2543 | 0.6746 | 0.2584 | 0.170* | 0.784 (7) |
H9C | −0.0833 | 0.5271 | 0.3496 | 0.170* | 0.784 (7) |
C10 | 0.2216 (8) | 0.0840 (9) | 0.1406 (5) | 0.1275 (19) | 0.733 (6) |
H10A | 0.1865 | 0.0309 | 0.2129 | 0.153* | 0.733 (6) |
H10B | 0.1072 | 0.1975 | 0.1039 | 0.153* | 0.733 (6) |
C11 | 0.2598 (15) | −0.0343 (12) | 0.0801 (5) | 0.133 (2) | 0.733 (6) |
H11A | 0.2744 | 0.0237 | 0.0046 | 0.199* | 0.733 (6) |
H11B | 0.1531 | −0.0677 | 0.0811 | 0.199* | 0.733 (6) |
H11C | 0.3792 | −0.1436 | 0.1115 | 0.199* | 0.733 (6) |
C8' | −0.024 (2) | 0.471 (3) | 0.2069 (13) | 0.0961 (13) | 0.216 (7) |
H8C | −0.0615 | 0.5126 | 0.1274 | 0.115* | 0.216 (7) |
H8D | −0.0636 | 0.3735 | 0.2412 | 0.115* | 0.216 (7) |
C9' | −0.112 (4) | 0.604 (4) | 0.247 (3) | 0.1132 (17) | 0.216 (7) |
H9D | −0.1637 | 0.5624 | 0.3148 | 0.170* | 0.216 (7) |
H9E | −0.2174 | 0.7016 | 0.1941 | 0.170* | 0.216 (7) |
H9F | −0.0209 | 0.6482 | 0.2619 | 0.170* | 0.216 (7) |
C10' | 0.340 (2) | 0.050 (2) | 0.0838 (15) | 0.1275 (19) | 0.267 (6) |
H10C | 0.2555 | 0.1460 | 0.0194 | 0.153* | 0.267 (6) |
H10D | 0.4623 | −0.0245 | 0.0579 | 0.153* | 0.267 (6) |
C11' | 0.254 (5) | −0.055 (4) | 0.1332 (16) | 0.133 (2) | 0.267 (6) |
H11D | 0.3195 | −0.1279 | 0.2064 | 0.199* | 0.267 (6) |
H11E | 0.2613 | −0.1348 | 0.0901 | 0.199* | 0.267 (6) |
H11F | 0.1188 | 0.0221 | 0.1394 | 0.199* | 0.267 (6) |
O1 | 0.2928 (3) | 0.4664 (3) | 0.46827 (17) | 0.0988 (6) | |
O2 | 0.3979 (3) | 0.5760 (2) | 0.31795 (16) | 0.0925 (6) | |
O3 | 0.7091 (3) | 0.2488 (3) | 0.12000 (14) | 0.0823 (5) | |
H3A | 0.711 (6) | 0.338 (3) | 0.072 (2) | 0.123* | |
O4 | 0.2695 (3) | 0.4578 (3) | 0.02454 (13) | 0.0976 (7) | |
O5 | 0.1853 (2) | 0.3993 (2) | 0.22587 (12) | 0.0713 (4) | |
O6 | 0.3792 (3) | 0.1322 (3) | 0.15899 (16) | 0.0909 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
P1 | 0.0644 (4) | 0.0939 (5) | 0.0463 (3) | −0.0471 (3) | 0.0061 (2) | −0.0157 (3) |
C1 | 0.0521 (10) | 0.0583 (10) | 0.0551 (10) | −0.0320 (8) | 0.0044 (8) | −0.0172 (8) |
C2 | 0.0544 (11) | 0.0607 (11) | 0.0555 (10) | −0.0299 (9) | 0.0010 (8) | −0.0181 (8) |
C3 | 0.0756 (15) | 0.0867 (15) | 0.0526 (11) | −0.0434 (13) | −0.0008 (10) | −0.0178 (10) |
C4 | 0.0763 (15) | 0.0768 (14) | 0.0667 (14) | −0.0378 (13) | −0.0155 (11) | 0.0005 (11) |
C5 | 0.0650 (14) | 0.0618 (12) | 0.0967 (18) | −0.0248 (11) | −0.0065 (13) | −0.0101 (12) |
C6 | 0.0627 (13) | 0.0669 (12) | 0.0765 (14) | −0.0292 (10) | 0.0083 (10) | −0.0249 (11) |
N1 | 0.0710 (12) | 0.0710 (11) | 0.0634 (11) | −0.0281 (9) | 0.0009 (9) | −0.0288 (9) |
C7 | 0.0570 (11) | 0.0715 (12) | 0.0523 (10) | −0.0357 (10) | 0.0109 (8) | −0.0193 (9) |
C8 | 0.069 (2) | 0.089 (3) | 0.091 (2) | −0.0168 (18) | 0.0057 (17) | 0.001 (2) |
C9 | 0.070 (3) | 0.132 (5) | 0.152 (5) | −0.049 (2) | 0.049 (3) | −0.061 (4) |
C10 | 0.105 (4) | 0.176 (5) | 0.175 (5) | −0.095 (4) | 0.042 (3) | −0.107 (4) |
C11 | 0.192 (5) | 0.146 (4) | 0.114 (5) | −0.114 (4) | −0.006 (6) | −0.048 (5) |
C8' | 0.069 (2) | 0.089 (3) | 0.091 (2) | −0.0168 (18) | 0.0057 (17) | 0.001 (2) |
C9' | 0.070 (3) | 0.132 (5) | 0.152 (5) | −0.049 (2) | 0.049 (3) | −0.061 (4) |
C10' | 0.105 (4) | 0.176 (5) | 0.175 (5) | −0.095 (4) | 0.042 (3) | −0.107 (4) |
C11' | 0.192 (5) | 0.146 (4) | 0.114 (5) | −0.114 (4) | −0.006 (6) | −0.048 (5) |
O1 | 0.0921 (14) | 0.1054 (14) | 0.0858 (12) | −0.0239 (11) | 0.0255 (11) | −0.0433 (11) |
O2 | 0.1164 (16) | 0.0613 (9) | 0.0886 (12) | −0.0296 (10) | 0.0086 (11) | −0.0210 (9) |
O3 | 0.0725 (11) | 0.1066 (14) | 0.0690 (10) | −0.0401 (10) | 0.0278 (8) | −0.0296 (9) |
O4 | 0.0928 (13) | 0.1595 (19) | 0.0495 (9) | −0.0782 (13) | 0.0003 (8) | −0.0059 (10) |
O5 | 0.0563 (9) | 0.0873 (10) | 0.0569 (8) | −0.0282 (8) | 0.0041 (7) | −0.0067 (7) |
O6 | 0.0959 (14) | 0.1074 (14) | 0.1021 (14) | −0.0641 (12) | 0.0083 (10) | −0.0463 (11) |
P1—O4 | 1.4653 (18) | C9—H9B | 0.9600 |
P1—O6 | 1.556 (2) | C9—H9C | 0.9600 |
P1—O5 | 1.5598 (16) | C10—C11 | 1.345 (9) |
P1—C7 | 1.822 (2) | C10—O6 | 1.461 (5) |
C1—C6 | 1.386 (3) | C10—H10A | 0.9700 |
C1—C2 | 1.398 (3) | C10—H10B | 0.9700 |
C1—C7 | 1.518 (3) | C11—H11A | 0.9600 |
C2—C3 | 1.383 (3) | C11—H11B | 0.9600 |
C2—N1 | 1.466 (3) | C11—H11C | 0.9600 |
C3—C4 | 1.364 (4) | C8'—C9' | 1.26 (3) |
C3—H3 | 0.9300 | C8'—O5 | 1.435 (15) |
C4—C5 | 1.381 (4) | C8'—H8C | 0.9700 |
C4—H4 | 0.9300 | C8'—H8D | 0.9700 |
C5—C6 | 1.375 (3) | C9'—H9D | 0.9600 |
C5—H5 | 0.9300 | C9'—H9E | 0.9600 |
C6—H6 | 0.9300 | C9'—H9F | 0.9600 |
N1—O1 | 1.213 (3) | C10'—C11' | 1.31 (3) |
N1—O2 | 1.215 (3) | C10'—O6 | 1.426 (13) |
C7—O3 | 1.417 (2) | C10'—H10C | 0.9700 |
C7—H7 | 0.9800 | C10'—H10D | 0.9700 |
C8—O5 | 1.463 (4) | C11'—H11D | 0.9600 |
C8—C9 | 1.465 (7) | C11'—H11E | 0.9600 |
C8—H8A | 0.9700 | C11'—H11F | 0.9600 |
C8—H8B | 0.9700 | O3—H3A | 0.817 (10) |
C9—H9A | 0.9600 | ||
O4—P1—O6 | 115.38 (12) | H8A—C8—H8B | 108.3 |
O4—P1—O5 | 114.16 (11) | C11—C10—O6 | 116.7 (6) |
O6—P1—O5 | 103.70 (10) | C11—C10—H10A | 108.1 |
O4—P1—C7 | 112.67 (10) | O6—C10—H10A | 108.1 |
O6—P1—C7 | 103.71 (10) | C11—C10—H10B | 108.1 |
O5—P1—C7 | 106.13 (9) | O6—C10—H10B | 108.1 |
C6—C1—C2 | 115.53 (19) | H10A—C10—H10B | 107.3 |
C6—C1—C7 | 118.91 (18) | C9'—C8'—O5 | 111 (2) |
C2—C1—C7 | 125.53 (17) | C9'—C8'—H8C | 109.4 |
C3—C2—C1 | 122.48 (19) | O5—C8'—H8C | 109.4 |
C3—C2—N1 | 115.65 (18) | C9'—C8'—H8D | 109.4 |
C1—C2—N1 | 121.86 (17) | O5—C8'—H8D | 109.4 |
C4—C3—C2 | 119.8 (2) | H8C—C8'—H8D | 108.0 |
C4—C3—H3 | 120.1 | C8'—C9'—H9D | 109.5 |
C2—C3—H3 | 120.1 | C8'—C9'—H9E | 109.5 |
C3—C4—C5 | 119.7 (2) | H9D—C9'—H9E | 109.5 |
C3—C4—H4 | 120.2 | C8'—C9'—H9F | 109.5 |
C5—C4—H4 | 120.2 | H9D—C9'—H9F | 109.5 |
C6—C5—C4 | 119.7 (2) | H9E—C9'—H9F | 109.5 |
C6—C5—H5 | 120.1 | C11'—C10'—O6 | 110.4 (15) |
C4—C5—H5 | 120.1 | C11'—C10'—H10C | 109.6 |
C5—C6—C1 | 122.8 (2) | O6—C10'—H10C | 109.6 |
C5—C6—H6 | 118.6 | C11'—C10'—H10D | 109.6 |
C1—C6—H6 | 118.6 | O6—C10'—H10D | 109.6 |
O1—N1—O2 | 122.7 (2) | H10C—C10'—H10D | 108.1 |
O1—N1—C2 | 117.8 (2) | C10'—C11'—H11D | 109.5 |
O2—N1—C2 | 119.50 (19) | C10'—C11'—H11E | 109.5 |
O3—C7—C1 | 109.76 (17) | H11D—C11'—H11E | 109.5 |
O3—C7—P1 | 106.87 (14) | C10'—C11'—H11F | 109.5 |
C1—C7—P1 | 113.49 (13) | H11D—C11'—H11F | 109.5 |
O3—C7—H7 | 108.9 | H11E—C11'—H11F | 109.5 |
C1—C7—H7 | 108.9 | C7—O3—H3A | 106 (3) |
P1—C7—H7 | 108.9 | C8'—O5—P1 | 125.3 (7) |
O5—C8—C9 | 109.0 (4) | C8—O5—P1 | 122.36 (19) |
O5—C8—H8A | 109.9 | C10'—O6—C10 | 45.2 (6) |
C9—C8—H8A | 109.9 | C10'—O6—P1 | 128.7 (8) |
O5—C8—H8B | 109.9 | C10—O6—P1 | 120.3 (3) |
C9—C8—H8B | 109.9 | ||
C6—C1—C2—C3 | −0.6 (3) | O6—P1—C7—C1 | −56.38 (16) |
C7—C1—C2—C3 | 177.55 (19) | O5—P1—C7—C1 | 52.54 (17) |
C6—C1—C2—N1 | 178.54 (19) | C9'—C8'—O5—C8 | −39.6 (17) |
C7—C1—C2—N1 | −3.3 (3) | C9'—C8'—O5—P1 | −139.1 (16) |
C1—C2—C3—C4 | 1.3 (3) | C9—C8—O5—C8' | 49.1 (11) |
N1—C2—C3—C4 | −177.8 (2) | C9—C8—O5—P1 | 156.6 (4) |
C2—C3—C4—C5 | −0.9 (4) | O4—P1—O5—C8' | 39.3 (10) |
C3—C4—C5—C6 | −0.2 (4) | O6—P1—O5—C8' | −87.1 (10) |
C4—C5—C6—C1 | 1.0 (4) | C7—P1—O5—C8' | 164.0 (10) |
C2—C1—C6—C5 | −0.6 (3) | O4—P1—O5—C8 | −7.3 (3) |
C7—C1—C6—C5 | −178.8 (2) | O6—P1—O5—C8 | −133.7 (3) |
C3—C2—N1—O1 | −29.3 (3) | C7—P1—O5—C8 | 117.4 (3) |
C1—C2—N1—O1 | 151.6 (2) | C11'—C10'—O6—C10 | −35.3 (18) |
C3—C2—N1—O2 | 149.4 (2) | C11'—C10'—O6—P1 | −131.9 (19) |
C1—C2—N1—O2 | −29.8 (3) | C11—C10—O6—C10' | 16.3 (12) |
C6—C1—C7—O3 | −19.2 (2) | C11—C10—O6—P1 | 132.5 (6) |
C2—C1—C7—O3 | 162.69 (18) | O4—P1—O6—C10' | −8.9 (8) |
C6—C1—C7—P1 | 100.3 (2) | O5—P1—O6—C10' | 116.7 (8) |
C2—C1—C7—P1 | −77.8 (2) | C7—P1—O6—C10' | −132.6 (8) |
O4—P1—C7—O3 | −60.70 (19) | O4—P1—O6—C10 | −63.6 (3) |
O6—P1—C7—O3 | 64.75 (16) | O5—P1—O6—C10 | 62.0 (3) |
O5—P1—C7—O3 | 173.68 (13) | C7—P1—O6—C10 | 172.7 (3) |
O4—P1—C7—C1 | 178.17 (15) |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3A···O4i | 0.82 (1) | 1.86 (1) | 2.671 (3) | 174 (4) |
Symmetry code: (i) −x+1, −y+1, −z. |
Experimental details
Crystal data | |
Chemical formula | C11H16NO6P |
Mr | 289.22 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 291 |
a, b, c (Å) | 7.5659 (13), 8.3844 (15), 12.557 (2) |
α, β, γ (°) | 73.356 (3), 87.391 (3), 64.432 (3) |
V (Å3) | 685.6 (2) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.22 |
Crystal size (mm) | 0.30 × 0.20 × 0.20 |
Data collection | |
Diffractometer | Bruker SMART 4K CCD area-detector |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6168, 2800, 2381 |
Rint | 0.020 |
(sin θ/λ)max (Å−1) | 0.628 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.052, 0.157, 1.05 |
No. of reflections | 2800 |
No. of parameters | 193 |
No. of restraints | 1 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.38, −0.20 |
Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3A···O4i | 0.82 (1) | 1.857 (11) | 2.671 (3) | 174 (4) |
Symmetry code: (i) −x+1, −y+1, −z. |
Acknowledgements
We thank Dr Xiang-Gao Meng for the X-ray data collection.
References
Allen, J. G., Atherton, F. R., Hall, M. J., Hassall, C. H., Holmes, S. W., Lambert, R. W., Nisbet, L. J. & Ringrose, P. S. (1978). Nature (London), 272, 56–58. CrossRef CAS PubMed Web of Science Google Scholar
Bruker (2001). SMART (Version 5.628) and SAINT (Version 6.45). Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Hirschmann, R., Smith, A. B., Taylor, C. M., Benkovic, P. A., Taylor, S., Yager, K. M., Sprengler, P. A. & Benkovic, S. J. (1994). Science, 265, 234–237. CrossRef CAS PubMed Web of Science Google Scholar
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany. Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Phosphonates, especially enantiomerically pure forms, are particularly important in connection with their remarkable biological activities. They have been used as enzyme inhibitors, antibacterial agents, anti-HIV agents, botryticides, and haptens for catalytic antibodies (Allen et al., 1978; Hirschmann et al., 1994). In this regard, the preparation of various optically active phosphonates with a diversity of structures is highly desirable for drug discovery and medicinal chemistry. The title compound (I) was obtained in the reaction of diphenylphosphite with an aromatic aldehyde in the presence of triethylamine.
In (I) (Fig. 1), the nitro group is twisted out of the mean plane of benzene ring at 29.91 (3)°. In the crystal (Fig. 2), intermolecular O—H···O hydrogen bonds (Table 1) link the molecules into centrosymmetric dimers (Fig. 2).