organic compounds
Diethyl [(4-nitrobenzamido)(phenyl)methyl]phosphonate
aThe Key Laboratory for Chemical Biology of Fujian Province, Xiamen University, Xiamen 361005, People's Republic of China, bSchool of Pharmaceutical Sciences, Xiamen University, Xiang-An South Road, Xiamen 361100, People's Republic of China, and cThe Third Institute of Oceanography of the State Oceanic Administration, Xiamen 361005, People's Republic of China
*Correspondence e-mail: hfang@tio.org.cn
In the title compound, C18H21N2O6P, the dihedral angle between the benzene and phenyl rings is 85.1 (2)°. In the crystal, molecules are linked via pairs of N—H⋯O(=P) hydrogen bonds, forming inversion dimers with graph-set notation R22(10). One of the ethyl groups is disordered over two sets of sites, with occupancies 0.746 (11) and 0.254 (11).
CCDC reference: 995975
Related literature
For the synthesis, see: Takahashi et al. (1994). For a related structure, see: Fang et al. (2004). For hydrogen bond graph-set notation, see: Bernstein et al. (1995).
Experimental
Crystal data
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Data collection: SMART (Bruker, 2001); cell SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97.
Supporting information
CCDC reference: 995975
10.1107/S1600536814007776/lh5697sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814007776/lh5697Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814007776/lh5697Isup3.cml
The hydrochloride of diethyl amino(phenyl)methylphosphonate was prepared according to the literature procedure (Takahashi et al., 1994). This ester (1.08 g, 5 mmol) was dissolved in dry tetrahydrofuran (20 ml) to which triethylamine (0.7 ml) was added, and the solution was added dropwise to 4-nitrobenzoyl chloride (0.9 g, 5 mmol) in the same solvent (10 ml) (see Fig. 1). After completion of the reaction, the precipitate was separated and the filtrate was extracted with ethyl acetate, dried over anhydrous MgSO4 and concentrated under vacuum. The residual liquid was purified by
to give the title compound. Single crystals suitable for X-ray analysis were obtained by slow evaporation of a petroleum ether - ethyl acetate solution (3:1 v/v) of the title compound.The H atoms were positioned geometrically (C—H = 0.93–0.98 Å) and were included in the
in the riding-model approximation with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(Cmethyl). The H atom bonded to the N atom was refined independently with Uiso(H) = 1.2Ueq(N).Data collection: SMART (Bruker, 2001); cell
SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).C18H21N2O6P | Z = 2 |
Mr = 392.34 | F(000) = 412 |
Triclinic, P1 | Dx = 1.339 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.112 (3) Å | Cell parameters from 1770 reflections |
b = 10.378 (4) Å | θ = 1.3–26.6° |
c = 12.583 (5) Å | µ = 0.18 mm−1 |
α = 106.321 (7)° | T = 293 K |
β = 90.188 (8)° | Block, colorless |
γ = 106.035 (7)° | 0.42 × 0.28 × 0.23 mm |
V = 973.3 (6) Å3 |
Bruker APEX diffractometer | 3375 independent reflections |
Radiation source: fine-focus sealed tube | 2719 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.028 |
ϕ and ω scan | θmax = 25.0°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | h = −9→9 |
Tmin = 0.929, Tmax = 0.960 | k = −12→12 |
4948 measured reflections | l = −8→14 |
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)] = 0.075 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.200 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.09 | w = 1/[σ2(Fo2) + (0.1021P)2 + 0.2844P] where P = (Fo2 + 2Fc2)/3 |
3375 reflections | (Δ/σ)max = 0.013 |
259 parameters | Δρmax = 0.48 e Å−3 |
1 restraint | Δρmin = −0.23 e Å−3 |
C18H21N2O6P | γ = 106.035 (7)° |
Mr = 392.34 | V = 973.3 (6) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.112 (3) Å | Mo Kα radiation |
b = 10.378 (4) Å | µ = 0.18 mm−1 |
c = 12.583 (5) Å | T = 293 K |
α = 106.321 (7)° | 0.42 × 0.28 × 0.23 mm |
β = 90.188 (8)° |
Bruker APEX diffractometer | 3375 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | 2719 reflections with I > 2σ(I) |
Tmin = 0.929, Tmax = 0.960 | Rint = 0.028 |
4948 measured reflections |
R[F2 > 2σ(F2)] = 0.075 | 1 restraint |
wR(F2) = 0.200 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.09 | Δρmax = 0.48 e Å−3 |
3375 reflections | Δρmin = −0.23 e Å−3 |
259 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 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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
P1 | 0.32681 (11) | 0.73988 (8) | 0.39408 (7) | 0.0472 (3) | |
O1 | 0.5803 (4) | 0.6502 (2) | 0.6389 (2) | 0.0749 (8) | |
O2 | 0.3346 (3) | 0.8870 (2) | 0.41776 (19) | 0.0576 (6) | |
O3 | 0.2957 (3) | 0.6646 (2) | 0.26662 (18) | 0.0591 (7) | |
O4 | 0.1843 (3) | 0.6511 (3) | 0.4480 (2) | 0.0675 (7) | |
O5 | 0.8608 (8) | 1.1843 (7) | 1.1263 (4) | 0.195 (3) | |
O6 | 0.6792 (9) | 1.2811 (5) | 1.0861 (4) | 0.172 (3) | |
N1 | 0.5688 (4) | 0.8136 (3) | 0.5566 (2) | 0.0510 (8) | |
H1N | 0.576 (5) | 0.893 (4) | 0.567 (3) | 0.061* | |
N2 | 0.7490 (9) | 1.1926 (6) | 1.0645 (4) | 0.124 (2) | |
C1 | 0.5887 (4) | 0.7714 (3) | 0.6449 (3) | 0.0504 (8) | |
C2 | 0.6243 (4) | 0.8826 (3) | 0.7554 (3) | 0.0513 (8) | |
C3 | 0.7279 (5) | 0.8703 (5) | 0.8364 (3) | 0.0724 (11) | |
H3A | 0.7716 | 0.7938 | 0.8219 | 0.087* | |
C4 | 0.7674 (6) | 0.9689 (6) | 0.9376 (4) | 0.0849 (13) | |
H4A | 0.8371 | 0.9599 | 0.9923 | 0.102* | |
C5 | 0.7041 (6) | 1.0796 (5) | 0.9574 (3) | 0.0797 (14) | |
C6 | 0.5969 (6) | 1.0951 (4) | 0.8798 (3) | 0.0790 (13) | |
H6A | 0.5523 | 1.1712 | 0.8957 | 0.095* | |
C7 | 0.5574 (5) | 0.9937 (4) | 0.7773 (3) | 0.0633 (10) | |
H7A | 0.4852 | 1.0014 | 0.7232 | 0.076* | |
C8 | 0.5261 (4) | 0.7180 (3) | 0.4444 (2) | 0.0469 (8) | |
H8A | 0.5015 | 0.6220 | 0.4493 | 0.056* | |
C9 | 0.6651 (4) | 0.7392 (3) | 0.3678 (3) | 0.0470 (8) | |
C10 | 0.6906 (5) | 0.6247 (4) | 0.2896 (3) | 0.0609 (9) | |
H10A | 0.6227 | 0.5351 | 0.2863 | 0.073* | |
C11 | 0.8151 (6) | 0.6411 (5) | 0.2164 (4) | 0.0807 (13) | |
H11A | 0.8304 | 0.5630 | 0.1638 | 0.097* | |
C12 | 0.9163 (6) | 0.7726 (5) | 0.2213 (4) | 0.0899 (14) | |
H12A | 1.0009 | 0.7845 | 0.1722 | 0.108* | |
C13 | 0.8918 (6) | 0.8858 (5) | 0.2989 (4) | 0.0892 (14) | |
H13A | 0.9605 | 0.9752 | 0.3024 | 0.107* | |
C14 | 0.7690 (5) | 0.8704 (4) | 0.3711 (3) | 0.0676 (10) | |
H14A | 0.7548 | 0.9492 | 0.4234 | 0.081* | |
C15 | 0.2262 (6) | 0.5160 (4) | 0.2178 (3) | 0.0771 (12) | |
H15A | 0.1059 | 0.4863 | 0.2312 | 0.092* | |
H15B | 0.2881 | 0.4670 | 0.2508 | 0.092* | |
C16 | 0.2434 (10) | 0.4827 (5) | 0.0984 (4) | 0.127 (2) | |
H16A | 0.1971 | 0.3834 | 0.0647 | 0.191* | |
H16B | 0.3628 | 0.5116 | 0.0857 | 0.191* | |
H16C | 0.1814 | 0.5312 | 0.0663 | 0.191* | |
C17 | 0.0434 (8) | 0.6943 (7) | 0.5001 (5) | 0.077 (2) | 0.746 (11) |
H17A | 0.0383 | 0.7802 | 0.4856 | 0.092* | 0.746 (11) |
H17B | −0.0641 | 0.6225 | 0.4697 | 0.092* | 0.746 (11) |
C18 | 0.0671 (14) | 0.7168 (8) | 0.6179 (5) | 0.114 (3) | 0.746 (11) |
H18A | −0.0335 | 0.7344 | 0.6517 | 0.171* | 0.746 (11) |
H18B | 0.1655 | 0.7961 | 0.6491 | 0.171* | 0.746 (11) |
H18C | 0.0851 | 0.6350 | 0.6314 | 0.171* | 0.746 (11) |
C17A | 0.1513 (16) | 0.7129 (17) | 0.5723 (15) | 0.060 (5)* | 0.254 (11) |
H17C | 0.1723 | 0.6563 | 0.6175 | 0.072* | 0.254 (11) |
H17D | 0.2236 | 0.8086 | 0.6033 | 0.072* | 0.254 (11) |
C18A | −0.0275 (17) | 0.707 (2) | 0.565 (2) | 0.082 (7)* | 0.254 (11) |
H18D | −0.0526 | 0.7677 | 0.6316 | 0.123* | 0.254 (11) |
H18E | −0.0973 | 0.6127 | 0.5546 | 0.123* | 0.254 (11) |
H18F | −0.0521 | 0.7373 | 0.5023 | 0.123* | 0.254 (11) |
U11 | U22 | U33 | U12 | U13 | U23 | |
P1 | 0.0631 (6) | 0.0300 (5) | 0.0477 (5) | 0.0161 (4) | 0.0095 (4) | 0.0075 (3) |
O1 | 0.130 (2) | 0.0410 (14) | 0.0592 (15) | 0.0318 (15) | 0.0001 (15) | 0.0164 (12) |
O2 | 0.0741 (15) | 0.0361 (12) | 0.0650 (15) | 0.0244 (11) | 0.0064 (12) | 0.0104 (11) |
O3 | 0.0810 (17) | 0.0402 (13) | 0.0496 (14) | 0.0137 (11) | 0.0008 (12) | 0.0066 (10) |
O4 | 0.0772 (17) | 0.0490 (15) | 0.0789 (18) | 0.0217 (13) | 0.0268 (14) | 0.0190 (13) |
O5 | 0.184 (5) | 0.208 (6) | 0.104 (3) | 0.025 (4) | −0.043 (4) | −0.058 (4) |
O6 | 0.290 (8) | 0.074 (3) | 0.094 (3) | 0.009 (4) | 0.056 (4) | −0.024 (2) |
N1 | 0.085 (2) | 0.0280 (13) | 0.0423 (15) | 0.0223 (14) | 0.0062 (13) | 0.0075 (12) |
N2 | 0.149 (5) | 0.095 (4) | 0.063 (3) | −0.031 (3) | 0.013 (3) | −0.013 (3) |
C1 | 0.069 (2) | 0.0373 (17) | 0.0475 (19) | 0.0213 (15) | 0.0079 (16) | 0.0103 (14) |
C2 | 0.063 (2) | 0.0424 (18) | 0.0457 (18) | 0.0104 (16) | 0.0098 (16) | 0.0135 (15) |
C3 | 0.083 (3) | 0.074 (3) | 0.057 (2) | 0.026 (2) | −0.002 (2) | 0.012 (2) |
C4 | 0.089 (3) | 0.091 (3) | 0.058 (2) | 0.012 (3) | −0.007 (2) | 0.008 (2) |
C5 | 0.092 (3) | 0.067 (3) | 0.045 (2) | −0.019 (2) | 0.016 (2) | 0.0007 (19) |
C6 | 0.119 (4) | 0.043 (2) | 0.065 (3) | 0.015 (2) | 0.037 (3) | 0.0082 (18) |
C7 | 0.093 (3) | 0.048 (2) | 0.049 (2) | 0.0206 (19) | 0.0153 (19) | 0.0135 (16) |
C8 | 0.072 (2) | 0.0264 (15) | 0.0436 (17) | 0.0201 (15) | 0.0071 (15) | 0.0066 (13) |
C9 | 0.0592 (19) | 0.0405 (17) | 0.0454 (17) | 0.0242 (15) | 0.0042 (15) | 0.0093 (14) |
C10 | 0.073 (2) | 0.046 (2) | 0.058 (2) | 0.0202 (17) | 0.0117 (18) | 0.0023 (16) |
C11 | 0.097 (3) | 0.065 (3) | 0.071 (3) | 0.031 (2) | 0.027 (2) | −0.001 (2) |
C12 | 0.090 (3) | 0.087 (3) | 0.093 (3) | 0.032 (3) | 0.045 (3) | 0.021 (3) |
C13 | 0.094 (3) | 0.060 (3) | 0.115 (4) | 0.024 (2) | 0.045 (3) | 0.026 (3) |
C14 | 0.083 (3) | 0.0388 (19) | 0.082 (3) | 0.0241 (18) | 0.029 (2) | 0.0121 (18) |
C15 | 0.112 (3) | 0.041 (2) | 0.068 (3) | 0.021 (2) | −0.009 (2) | 0.0017 (18) |
C16 | 0.230 (7) | 0.070 (3) | 0.058 (3) | 0.031 (4) | −0.006 (4) | −0.007 (2) |
C17 | 0.072 (4) | 0.077 (4) | 0.093 (5) | 0.030 (3) | 0.024 (4) | 0.033 (3) |
C18 | 0.160 (9) | 0.101 (6) | 0.080 (5) | 0.033 (5) | 0.055 (6) | 0.028 (4) |
P1—O2 | 1.454 (2) | C9—C10 | 1.379 (5) |
P1—O4 | 1.553 (3) | C10—C11 | 1.377 (5) |
P1—O3 | 1.559 (2) | C10—H10A | 0.9300 |
P1—C8 | 1.829 (3) | C11—C12 | 1.369 (6) |
O1—C1 | 1.222 (4) | C11—H11A | 0.9300 |
O3—C15 | 1.435 (4) | C12—C13 | 1.364 (6) |
O4—C17 | 1.435 (6) | C12—H12A | 0.9300 |
O4—C17A | 1.569 (18) | C13—C14 | 1.358 (6) |
O5—N2 | 1.229 (9) | C13—H13A | 0.9300 |
O6—N2 | 1.178 (9) | C14—H14A | 0.9300 |
N1—C1 | 1.328 (4) | C15—C16 | 1.460 (6) |
N1—C8 | 1.454 (4) | C15—H15A | 0.9700 |
N1—H1N | 0.78 (4) | C15—H15B | 0.9700 |
N2—C5 | 1.482 (6) | C16—H16A | 0.9600 |
C1—C2 | 1.503 (5) | C16—H16B | 0.9600 |
C2—C7 | 1.367 (5) | C16—H16C | 0.9600 |
C2—C3 | 1.374 (5) | C17—C18 | 1.437 (8) |
C3—C4 | 1.363 (6) | C17—H17A | 0.9700 |
C3—H3A | 0.9300 | C17—H17B | 0.9700 |
C4—C5 | 1.345 (7) | C18—H18A | 0.9600 |
C4—H4A | 0.9300 | C18—H18B | 0.9600 |
C5—C6 | 1.377 (7) | C18—H18C | 0.9600 |
C6—C7 | 1.387 (5) | C17A—C18A | 1.437 (8) |
C6—H6A | 0.9300 | C17A—H17C | 0.9700 |
C7—H7A | 0.9300 | C17A—H17D | 0.9700 |
C8—C9 | 1.497 (5) | C18A—H18D | 0.9600 |
C8—H8A | 0.9800 | C18A—H18E | 0.9600 |
C9—C14 | 1.379 (5) | C18A—H18F | 0.9600 |
O2—P1—O4 | 115.90 (15) | C11—C10—C9 | 121.0 (4) |
O2—P1—O3 | 111.00 (13) | C11—C10—H10A | 119.5 |
O4—P1—O3 | 105.86 (14) | C9—C10—H10A | 119.5 |
O2—P1—C8 | 111.80 (13) | C12—C11—C10 | 119.8 (4) |
O4—P1—C8 | 103.95 (15) | C12—C11—H11A | 120.1 |
O3—P1—C8 | 107.74 (14) | C10—C11—H11A | 120.1 |
C15—O3—P1 | 124.6 (2) | C13—C12—C11 | 119.2 (4) |
C17—O4—P1 | 125.5 (3) | C13—C12—H12A | 120.4 |
C17—O4—C17A | 46.7 (5) | C11—C12—H12A | 120.4 |
P1—O4—C17A | 119.6 (6) | C14—C13—C12 | 121.3 (4) |
C1—N1—C8 | 122.9 (3) | C14—C13—H13A | 119.4 |
C1—N1—H1N | 118 (3) | C12—C13—H13A | 119.4 |
C8—N1—H1N | 119 (3) | C13—C14—C9 | 120.7 (4) |
O6—N2—O5 | 124.5 (5) | C13—C14—H14A | 119.7 |
O6—N2—C5 | 120.8 (7) | C9—C14—H14A | 119.7 |
O5—N2—C5 | 114.8 (7) | O3—C15—C16 | 108.7 (4) |
O1—C1—N1 | 123.2 (3) | O3—C15—H15A | 110.0 |
O1—C1—C2 | 120.7 (3) | C16—C15—H15A | 110.0 |
N1—C1—C2 | 116.1 (3) | O3—C15—H15B | 110.0 |
C7—C2—C3 | 119.6 (3) | C16—C15—H15B | 110.0 |
C7—C2—C1 | 122.4 (3) | H15A—C15—H15B | 108.3 |
C3—C2—C1 | 118.0 (3) | C15—C16—H16A | 109.5 |
C4—C3—C2 | 120.8 (4) | C15—C16—H16B | 109.5 |
C4—C3—H3A | 119.6 | H16A—C16—H16B | 109.5 |
C2—C3—H3A | 119.6 | C15—C16—H16C | 109.5 |
C5—C4—C3 | 119.1 (4) | H16A—C16—H16C | 109.5 |
C5—C4—H4A | 120.5 | H16B—C16—H16C | 109.5 |
C3—C4—H4A | 120.5 | C18—C17—O4 | 109.3 (6) |
C4—C5—C6 | 122.3 (4) | C18—C17—H17A | 109.8 |
C4—C5—N2 | 121.2 (6) | O4—C17—H17A | 109.8 |
C6—C5—N2 | 116.5 (6) | C18—C17—H17B | 109.8 |
C5—C6—C7 | 118.0 (4) | O4—C17—H17B | 109.8 |
C5—C6—H6A | 121.0 | H17A—C17—H17B | 108.3 |
C7—C6—H6A | 121.0 | C18A—C17A—O4 | 102.9 (15) |
C2—C7—C6 | 120.2 (4) | C18A—C17A—H17C | 111.2 |
C2—C7—H7A | 119.9 | O4—C17A—H17C | 111.2 |
C6—C7—H7A | 119.9 | C18A—C17A—H17D | 111.2 |
N1—C8—C9 | 114.6 (3) | O4—C17A—H17D | 111.2 |
N1—C8—P1 | 105.6 (2) | H17C—C17A—H17D | 109.1 |
C9—C8—P1 | 112.3 (2) | C17A—C18A—H18D | 109.5 |
N1—C8—H8A | 108.1 | C17A—C18A—H18E | 109.5 |
C9—C8—H8A | 108.1 | H18D—C18A—H18E | 109.5 |
P1—C8—H8A | 108.1 | C17A—C18A—H18F | 109.5 |
C14—C9—C10 | 118.0 (3) | H18D—C18A—H18F | 109.5 |
C14—C9—C8 | 122.3 (3) | H18E—C18A—H18F | 109.5 |
C10—C9—C8 | 119.7 (3) | ||
O2—P1—O3—C15 | −158.4 (3) | C1—C2—C7—C6 | −178.7 (3) |
O4—P1—O3—C15 | −31.9 (3) | C5—C6—C7—C2 | −0.1 (6) |
C8—P1—O3—C15 | 78.9 (3) | C1—N1—C8—C9 | −113.4 (3) |
O2—P1—O4—C17 | 12.4 (4) | C1—N1—C8—P1 | 122.6 (3) |
O3—P1—O4—C17 | −111.2 (4) | O2—P1—C8—N1 | 46.0 (2) |
C8—P1—O4—C17 | 135.5 (4) | O4—P1—C8—N1 | −79.8 (2) |
O2—P1—O4—C17A | −43.3 (6) | O3—P1—C8—N1 | 168.18 (18) |
O3—P1—O4—C17A | −166.8 (6) | O2—P1—C8—C9 | −79.5 (2) |
C8—P1—O4—C17A | 79.8 (6) | O4—P1—C8—C9 | 154.8 (2) |
C8—N1—C1—O1 | 3.3 (6) | O3—P1—C8—C9 | 42.7 (2) |
C8—N1—C1—C2 | −177.2 (3) | N1—C8—C9—C14 | −37.0 (4) |
O1—C1—C2—C7 | −147.5 (4) | P1—C8—C9—C14 | 83.4 (4) |
N1—C1—C2—C7 | 32.9 (5) | N1—C8—C9—C10 | 143.8 (3) |
O1—C1—C2—C3 | 32.3 (5) | P1—C8—C9—C10 | −95.8 (3) |
N1—C1—C2—C3 | −147.2 (3) | C14—C9—C10—C11 | −0.5 (6) |
C7—C2—C3—C4 | −1.2 (6) | C8—C9—C10—C11 | 178.6 (3) |
C1—C2—C3—C4 | 178.9 (4) | C9—C10—C11—C12 | 0.4 (7) |
C2—C3—C4—C5 | −0.3 (7) | C10—C11—C12—C13 | −0.1 (8) |
C3—C4—C5—C6 | 1.7 (7) | C11—C12—C13—C14 | −0.1 (8) |
C3—C4—C5—N2 | −177.5 (4) | C12—C13—C14—C9 | −0.1 (8) |
O6—N2—C5—C4 | −171.8 (5) | C10—C9—C14—C13 | 0.4 (6) |
O5—N2—C5—C4 | 7.7 (7) | C8—C9—C14—C13 | −178.8 (4) |
O6—N2—C5—C6 | 9.0 (7) | P1—O3—C15—C16 | −170.5 (4) |
O5—N2—C5—C6 | −171.6 (5) | P1—O4—C17—C18 | −110.7 (5) |
C4—C5—C6—C7 | −1.5 (6) | C17A—O4—C17—C18 | −11.4 (9) |
N2—C5—C6—C7 | 177.7 (3) | C17—O4—C17A—C18A | 10.2 (11) |
C3—C2—C7—C6 | 1.4 (5) | P1—O4—C17A—C18A | 122.7 (11) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O2i | 0.78 (4) | 2.15 (4) | 2.909 (4) | 164 (4) |
Symmetry code: (i) −x+1, −y+2, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O2i | 0.78 (4) | 2.15 (4) | 2.909 (4) | 164 (4) |
Symmetry code: (i) −x+1, −y+2, −z+1. |
Acknowledgements
This work was supported by the National Science Foundation of China (No. 81302652) and the special financial fund of the innovative development of marine economic demonstration project, GD2012-D01–001.
References
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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.
The title compound (I) was synthesized for a study of its antimicrobial activity against Bacillus subtilis. This aminophosphonate derivative was found to have weak antimicrobial activity (inhibition zone = 7 mm). The molecular structure of the title compound is shown in Fig. 1. The dihedral angle between the benzene (C2–C7) ring and phenyl (C9–C14) ring is 85.1 (2)°. In the crystal, molecules are linked via pairs of N—H···O(═P) hydrogen bonds forming inversion dimers with with graph-set notation R22(10) (Bernstein et al., 1995). One of the ethyl groups (C17/C18) is disordered over two sets of sites with occupancies 0.746 (11) and 0.254 (11). Bond lenths and angles in (I) are in agreement with the values reported for a similar structure (Fang et al., 2004).