organic compounds
N,N′-Dibenzyl-N′′-(4-bromobenzoyl)-N,N′-dimethylphosphoric triamide
aDepartment of Chemistry, Alzahra University, Vanak, Tehran, Iran, bLaboratoire DECMET, UMR CNRS 7513, Université Louis Pasteur, Strasbourg, France, and cDépartement de Chimie, Faculté des Sciences et Techniques, Université de Nouakchott, Nouakchott, Mauritania
*Correspondence e-mail: dehganpour_farasha@yahoo.com
In the title compound, C23H25BrN3O2P, the P atom has a distorted tetrahedral coordination. In the the molecules form centrosymmetric dimers via pairs of essentially linear N—H⋯O hydrogen bonds.
Related literature
For the use of carbacylamidophosphate, see: Barak et al. (2000); Burla et al. (1989); Gubina et al. (2000); Mallender et al. (2000); Trush et al. (2003). For related structures, see: Trush et al. (1999).
Experimental
Crystal data
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Data collection
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Refinement
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Data collection: COLLECT (Nonius, 1998); cell DENZO (Otwinowski & Minor, 1997); data reduction: DENZO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.
Supporting information
10.1107/S1600536808004777/zl2095sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808004777/zl2095Isup2.hkl
Compound (I) was synthesized via the reaction of BrC6H4C(O)NHP(O)Cl2 with two molecules of methylbenzylamine in a 1:4 molar ratio. Methylbenzylamine was added dropwise to a mixture of BrC6H4C(O)NHP(O)Cl2 in chloroform while stirring at room temperature for 4 h. The product was filtered off and then washed with cold water. The compound was recrystallized from ethanol (yield 88%). Analysis, calculated for C23 H25 Br N3 O2 P: C 56.80, H 5.18, N 8.64%; found: C 56.81, H 5.19, N 8.64%.
H atoms were placed in idealized positions with C—H distances at 0.97, 0.96 and 0.93 Å for CH2, CH3 and aromatic CH groups, respectively using a riding model. Uiso(H) for H was assigned as 1.2 Ueq(Ci) of the attached C atoms (1.5 for methyl). No absorption correction was applied due to the small cystal size and the sufficiently low µ value.
Data collection: COLLECT (Nonius, 1998); cell
DENZO (Otwinowski & Minor, 1997); data reduction: DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).C23H25BrN3O2P | F(000) = 1000 |
Mr = 486.34 | Dx = 1.397 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 10293 reflections |
a = 9.0140 (4) Å | θ = 1.0–27.5° |
b = 13.2690 (5) Å | µ = 1.87 mm−1 |
c = 19.377 (1) Å | T = 293 K |
β = 94.1500 (14)° | Prism, colorless |
V = 2311.54 (18) Å3 | 0.11 × 0.09 × 0.08 mm |
Z = 4 |
Nonius KappaCCD diffractometer | 2593 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.051 |
Graphite monochromator | θmax = 27.5°, θmin = 1.9° |
π scans | h = −11→10 |
12951 measured reflections | k = −17→14 |
5214 independent reflections | l = −17→25 |
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)] = 0.053 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.135 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.052P)2 + 0.3719P] where P = (Fo2 + 2Fc2)/3 |
5214 reflections | (Δ/σ)max = 0.001 |
271 parameters | Δρmax = 0.27 e Å−3 |
0 restraints | Δρmin = −0.62 e Å−3 |
C23H25BrN3O2P | V = 2311.54 (18) Å3 |
Mr = 486.34 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 9.0140 (4) Å | µ = 1.87 mm−1 |
b = 13.2690 (5) Å | T = 293 K |
c = 19.377 (1) Å | 0.11 × 0.09 × 0.08 mm |
β = 94.1500 (14)° |
Nonius KappaCCD diffractometer | 2593 reflections with I > 2σ(I) |
12951 measured reflections | Rint = 0.051 |
5214 independent reflections |
R[F2 > 2σ(F2)] = 0.053 | 0 restraints |
wR(F2) = 0.135 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.27 e Å−3 |
5214 reflections | Δρmin = −0.62 e Å−3 |
271 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 | ||
Br1 | 0.97528 (7) | 0.99976 (3) | 0.19720 (3) | 0.1095 (3) | |
P1 | 0.97988 (9) | 0.37741 (5) | 0.08475 (4) | 0.0427 (2) | |
O1 | 0.8889 (3) | 0.48944 (15) | 0.21515 (13) | 0.0676 (7) | |
O2 | 1.0335 (2) | 0.37714 (14) | 0.01466 (10) | 0.0493 (5) | |
N1 | 0.9570 (3) | 0.49921 (14) | 0.10487 (13) | 0.0453 (6) | |
H1 | 0.9661 | 0.5414 | 0.0717 | 0.054* | |
N2 | 1.0988 (3) | 0.32013 (17) | 0.13878 (12) | 0.0478 (7) | |
N3 | 0.8203 (3) | 0.32336 (16) | 0.09738 (13) | 0.0474 (6) | |
C1 | 0.9380 (3) | 0.6529 (2) | 0.17215 (15) | 0.0440 (7) | |
C2 | 0.8517 (3) | 0.7031 (2) | 0.21718 (16) | 0.0505 (8) | |
H2 | 0.7872 | 0.6665 | 0.2429 | 0.061* | |
C3 | 0.8593 (4) | 0.8061 (2) | 0.22469 (17) | 0.0588 (9) | |
H3 | 0.7986 | 0.8395 | 0.2541 | 0.071* | |
C4 | 0.9584 (4) | 0.8585 (2) | 0.18784 (18) | 0.0615 (10) | |
C5 | 1.0478 (4) | 0.8100 (2) | 0.14387 (19) | 0.0682 (10) | |
H5 | 1.1152 | 0.8465 | 0.1196 | 0.082* | |
C6 | 1.0366 (4) | 0.7066 (2) | 0.13596 (17) | 0.0564 (9) | |
H6 | 1.0961 | 0.6733 | 0.1060 | 0.068* | |
C7 | 0.9257 (3) | 0.5404 (2) | 0.16691 (17) | 0.0486 (8) | |
C8 | 1.0706 (4) | 0.2882 (3) | 0.20873 (17) | 0.0669 (10) | |
H8A | 0.9697 | 0.3039 | 0.2176 | 0.100* | |
H8B | 1.1373 | 0.3228 | 0.2416 | 0.100* | |
H8C | 1.0861 | 0.2168 | 0.2131 | 0.100* | |
C9 | 1.2491 (4) | 0.2979 (2) | 0.11888 (18) | 0.0566 (9) | |
H9A | 1.3200 | 0.3171 | 0.1566 | 0.068* | |
H9B | 1.2686 | 0.3390 | 0.0792 | 0.068* | |
C10 | 1.2746 (3) | 0.1886 (2) | 0.10116 (17) | 0.0506 (8) | |
C11 | 1.3680 (4) | 0.1286 (3) | 0.14281 (19) | 0.0680 (10) | |
H11 | 1.4111 | 0.1543 | 0.1842 | 0.082* | |
C12 | 1.3988 (5) | 0.0301 (3) | 0.1237 (3) | 0.0867 (13) | |
H12 | 1.4631 | −0.0095 | 0.1520 | 0.104* | |
C13 | 1.3348 (5) | −0.0078 (3) | 0.0640 (3) | 0.0903 (14) | |
H13 | 1.3546 | −0.0738 | 0.0513 | 0.108* | |
C14 | 1.2410 (5) | 0.0505 (3) | 0.0221 (2) | 0.0830 (12) | |
H14 | 1.1980 | 0.0241 | −0.0191 | 0.100* | |
C15 | 1.2100 (4) | 0.1478 (3) | 0.04062 (19) | 0.0646 (10) | |
H15 | 1.1450 | 0.1865 | 0.0122 | 0.078* | |
C16 | 0.8132 (4) | 0.2134 (2) | 0.0867 (2) | 0.0710 (11) | |
H16A | 0.9095 | 0.1846 | 0.0981 | 0.107* | |
H16B | 0.7829 | 0.1994 | 0.0391 | 0.107* | |
H16C | 0.7425 | 0.1848 | 0.1158 | 0.107* | |
C17 | 0.6770 (3) | 0.3738 (2) | 0.08216 (17) | 0.0545 (8) | |
H17A | 0.6872 | 0.4439 | 0.0959 | 0.065* | |
H17B | 0.6043 | 0.3433 | 0.1102 | 0.065* | |
C18 | 0.6182 (3) | 0.3696 (2) | 0.00736 (16) | 0.0463 (8) | |
C19 | 0.5215 (4) | 0.2942 (3) | −0.01586 (19) | 0.0655 (10) | |
H19 | 0.4908 | 0.2463 | 0.0152 | 0.079* | |
C20 | 0.4698 (4) | 0.2890 (3) | −0.0847 (2) | 0.0781 (11) | |
H20 | 0.4056 | 0.2374 | −0.0998 | 0.094* | |
C21 | 0.5125 (4) | 0.3591 (3) | −0.13033 (19) | 0.0726 (11) | |
H21 | 0.4761 | 0.3562 | −0.1764 | 0.087* | |
C22 | 0.6101 (4) | 0.4348 (3) | −0.10826 (19) | 0.0665 (10) | |
H22 | 0.6410 | 0.4823 | −0.1395 | 0.080* | |
C23 | 0.6611 (4) | 0.4394 (2) | −0.03991 (19) | 0.0574 (9) | |
H23 | 0.7261 | 0.4907 | −0.0251 | 0.069* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.1798 (6) | 0.0408 (2) | 0.1100 (5) | −0.0035 (2) | 0.0253 (4) | −0.0180 (2) |
P1 | 0.0553 (5) | 0.0330 (4) | 0.0398 (5) | 0.0004 (4) | 0.0042 (4) | 0.0012 (3) |
O1 | 0.108 (2) | 0.0516 (14) | 0.0455 (14) | −0.0064 (12) | 0.0206 (14) | 0.0020 (11) |
O2 | 0.0716 (14) | 0.0369 (11) | 0.0401 (13) | 0.0037 (9) | 0.0092 (11) | 0.0006 (9) |
N1 | 0.0654 (17) | 0.0327 (13) | 0.0383 (15) | −0.0008 (11) | 0.0068 (13) | 0.0019 (10) |
N2 | 0.0522 (17) | 0.0476 (14) | 0.0432 (16) | 0.0058 (12) | 0.0009 (13) | 0.0108 (12) |
N3 | 0.0476 (16) | 0.0404 (14) | 0.0542 (17) | −0.0004 (11) | 0.0035 (13) | 0.0044 (12) |
C1 | 0.0524 (19) | 0.0436 (17) | 0.0356 (18) | 0.0029 (14) | −0.0001 (15) | −0.0034 (14) |
C2 | 0.052 (2) | 0.0533 (19) | 0.0466 (19) | −0.0017 (15) | 0.0035 (16) | −0.0025 (16) |
C3 | 0.071 (3) | 0.053 (2) | 0.051 (2) | 0.0103 (17) | 0.0030 (18) | −0.0144 (17) |
C4 | 0.087 (3) | 0.0387 (18) | 0.058 (2) | 0.0037 (17) | 0.001 (2) | −0.0077 (16) |
C5 | 0.091 (3) | 0.053 (2) | 0.063 (2) | −0.0175 (18) | 0.016 (2) | −0.0092 (18) |
C6 | 0.073 (2) | 0.0428 (18) | 0.056 (2) | −0.0014 (16) | 0.0195 (18) | −0.0081 (16) |
C7 | 0.060 (2) | 0.0449 (17) | 0.042 (2) | 0.0006 (15) | 0.0078 (16) | −0.0022 (16) |
C8 | 0.090 (3) | 0.063 (2) | 0.047 (2) | 0.0128 (19) | 0.0006 (19) | 0.0097 (17) |
C9 | 0.051 (2) | 0.0508 (19) | 0.067 (2) | −0.0036 (15) | −0.0023 (17) | 0.0058 (17) |
C10 | 0.0425 (19) | 0.0478 (18) | 0.062 (2) | −0.0007 (14) | 0.0061 (17) | 0.0063 (17) |
C11 | 0.064 (2) | 0.063 (2) | 0.075 (3) | 0.0067 (18) | −0.006 (2) | 0.005 (2) |
C12 | 0.092 (3) | 0.068 (3) | 0.099 (4) | 0.028 (2) | −0.006 (3) | 0.016 (3) |
C13 | 0.096 (3) | 0.063 (3) | 0.113 (4) | 0.017 (2) | 0.012 (3) | −0.011 (2) |
C14 | 0.083 (3) | 0.078 (3) | 0.087 (3) | 0.005 (2) | 0.004 (2) | −0.021 (2) |
C15 | 0.062 (2) | 0.062 (2) | 0.068 (3) | 0.0057 (18) | −0.004 (2) | 0.0013 (19) |
C16 | 0.074 (3) | 0.0398 (18) | 0.098 (3) | −0.0097 (16) | −0.003 (2) | 0.0053 (19) |
C17 | 0.052 (2) | 0.058 (2) | 0.054 (2) | 0.0010 (16) | 0.0072 (17) | −0.0010 (16) |
C18 | 0.0409 (18) | 0.0485 (18) | 0.050 (2) | 0.0054 (14) | 0.0055 (15) | −0.0038 (15) |
C19 | 0.061 (2) | 0.070 (2) | 0.064 (3) | −0.0133 (18) | 0.0004 (19) | 0.005 (2) |
C20 | 0.081 (3) | 0.073 (2) | 0.077 (3) | −0.020 (2) | −0.015 (2) | 0.001 (2) |
C21 | 0.083 (3) | 0.077 (3) | 0.055 (2) | 0.007 (2) | −0.011 (2) | −0.004 (2) |
C22 | 0.071 (3) | 0.068 (2) | 0.059 (3) | 0.0012 (19) | −0.002 (2) | 0.0139 (19) |
C23 | 0.059 (2) | 0.050 (2) | 0.062 (2) | −0.0029 (15) | −0.0046 (18) | 0.0030 (17) |
Br1—C4 | 1.889 (3) | C10—C11 | 1.377 (4) |
P1—O2 | 1.474 (2) | C10—C15 | 1.382 (4) |
P1—N2 | 1.631 (2) | C11—C12 | 1.392 (5) |
P1—N3 | 1.642 (2) | C11—H11 | 0.9300 |
P1—N1 | 1.679 (2) | C12—C13 | 1.353 (6) |
O1—C7 | 1.218 (4) | C12—H12 | 0.9300 |
N1—C7 | 1.368 (4) | C13—C14 | 1.369 (6) |
N1—H1 | 0.8600 | C13—H13 | 0.9300 |
N2—C8 | 1.460 (4) | C14—C15 | 1.375 (5) |
N2—C9 | 1.465 (4) | C14—H14 | 0.9300 |
N3—C17 | 1.465 (4) | C15—H15 | 0.9300 |
N3—C16 | 1.474 (4) | C16—H16A | 0.9600 |
C1—C6 | 1.370 (4) | C16—H16B | 0.9600 |
C1—C2 | 1.381 (4) | C16—H16C | 0.9600 |
C1—C7 | 1.501 (4) | C17—C18 | 1.508 (4) |
C2—C3 | 1.376 (4) | C17—H17A | 0.9700 |
C2—H2 | 0.9300 | C17—H17B | 0.9700 |
C3—C4 | 1.372 (5) | C18—C23 | 1.377 (4) |
C3—H3 | 0.9300 | C18—C19 | 1.381 (4) |
C4—C5 | 1.374 (5) | C19—C20 | 1.382 (5) |
C5—C6 | 1.385 (4) | C19—H19 | 0.9300 |
C5—H5 | 0.9300 | C20—C21 | 1.359 (5) |
C6—H6 | 0.9300 | C20—H20 | 0.9300 |
C8—H8A | 0.9600 | C21—C22 | 1.382 (5) |
C8—H8B | 0.9600 | C21—H21 | 0.9300 |
C8—H8C | 0.9600 | C22—C23 | 1.371 (5) |
C9—C10 | 1.512 (4) | C22—H22 | 0.9300 |
C9—H9A | 0.9700 | C23—H23 | 0.9300 |
C9—H9B | 0.9700 | ||
O2—P1—N2 | 110.25 (13) | C11—C10—C15 | 118.3 (3) |
O2—P1—N3 | 119.05 (13) | C11—C10—C9 | 121.2 (3) |
N2—P1—N3 | 104.06 (12) | C15—C10—C9 | 120.4 (3) |
O2—P1—N1 | 105.69 (12) | C10—C11—C12 | 120.8 (3) |
N2—P1—N1 | 112.69 (13) | C10—C11—H11 | 119.6 |
N3—P1—N1 | 105.20 (12) | C12—C11—H11 | 119.6 |
C7—N1—P1 | 128.7 (2) | C13—C12—C11 | 119.7 (4) |
C7—N1—H1 | 115.7 | C13—C12—H12 | 120.1 |
P1—N1—H1 | 115.7 | C11—C12—H12 | 120.1 |
C8—N2—C9 | 114.4 (2) | C12—C13—C14 | 120.3 (4) |
C8—N2—P1 | 125.5 (2) | C12—C13—H13 | 119.9 |
C9—N2—P1 | 120.1 (2) | C14—C13—H13 | 119.9 |
C17—N3—C16 | 113.3 (2) | C13—C14—C15 | 120.3 (4) |
C17—N3—P1 | 122.65 (19) | C13—C14—H14 | 119.8 |
C16—N3—P1 | 116.2 (2) | C15—C14—H14 | 119.8 |
C6—C1—C2 | 119.3 (3) | C14—C15—C10 | 120.6 (3) |
C6—C1—C7 | 122.0 (3) | C14—C15—H15 | 119.7 |
C2—C1—C7 | 118.7 (3) | C10—C15—H15 | 119.7 |
C3—C2—C1 | 121.3 (3) | N3—C16—H16A | 109.5 |
C3—C2—H2 | 119.3 | N3—C16—H16B | 109.5 |
C1—C2—H2 | 119.3 | H16A—C16—H16B | 109.5 |
C4—C3—C2 | 118.5 (3) | N3—C16—H16C | 109.5 |
C4—C3—H3 | 120.7 | H16A—C16—H16C | 109.5 |
C2—C3—H3 | 120.7 | H16B—C16—H16C | 109.5 |
C3—C4—C5 | 121.3 (3) | N3—C17—C18 | 114.8 (3) |
C3—C4—Br1 | 120.2 (3) | N3—C17—H17A | 108.6 |
C5—C4—Br1 | 118.5 (3) | C18—C17—H17A | 108.6 |
C4—C5—C6 | 119.4 (3) | N3—C17—H17B | 108.6 |
C4—C5—H5 | 120.3 | C18—C17—H17B | 108.6 |
C6—C5—H5 | 120.3 | H17A—C17—H17B | 107.5 |
C1—C6—C5 | 120.2 (3) | C23—C18—C19 | 118.1 (3) |
C1—C6—H6 | 119.9 | C23—C18—C17 | 121.2 (3) |
C5—C6—H6 | 119.9 | C19—C18—C17 | 120.7 (3) |
O1—C7—N1 | 122.5 (3) | C18—C19—C20 | 120.7 (3) |
O1—C7—C1 | 121.5 (3) | C18—C19—H19 | 119.6 |
N1—C7—C1 | 116.0 (3) | C20—C19—H19 | 119.6 |
N2—C8—H8A | 109.5 | C21—C20—C19 | 120.2 (3) |
N2—C8—H8B | 109.5 | C21—C20—H20 | 119.9 |
H8A—C8—H8B | 109.5 | C19—C20—H20 | 119.9 |
N2—C8—H8C | 109.5 | C20—C21—C22 | 120.0 (3) |
H8A—C8—H8C | 109.5 | C20—C21—H21 | 120.0 |
H8B—C8—H8C | 109.5 | C22—C21—H21 | 120.0 |
N2—C9—C10 | 114.3 (2) | C23—C22—C21 | 119.5 (3) |
N2—C9—H9A | 108.7 | C23—C22—H22 | 120.3 |
C10—C9—H9A | 108.7 | C21—C22—H22 | 120.3 |
N2—C9—H9B | 108.7 | C22—C23—C18 | 121.5 (3) |
C10—C9—H9B | 108.7 | C22—C23—H23 | 119.3 |
H9A—C9—H9B | 107.6 | C18—C23—H23 | 119.3 |
O2—P1—N1—C7 | −171.6 (3) | C2—C1—C7—O1 | −27.1 (4) |
N2—P1—N1—C7 | −51.2 (3) | C6—C1—C7—N1 | −30.6 (4) |
N3—P1—N1—C7 | 61.6 (3) | C2—C1—C7—N1 | 152.3 (3) |
O2—P1—N2—C8 | −167.1 (2) | C8—N2—C9—C10 | 76.2 (3) |
N3—P1—N2—C8 | −38.3 (3) | P1—N2—C9—C10 | −104.6 (3) |
N1—P1—N2—C8 | 75.1 (3) | N2—C9—C10—C11 | −111.6 (3) |
O2—P1—N2—C9 | 13.8 (2) | N2—C9—C10—C15 | 71.6 (4) |
N3—P1—N2—C9 | 142.6 (2) | C15—C10—C11—C12 | 1.2 (5) |
N1—P1—N2—C9 | −104.0 (2) | C9—C10—C11—C12 | −175.6 (3) |
O2—P1—N3—C17 | −81.9 (3) | C10—C11—C12—C13 | −0.8 (6) |
N2—P1—N3—C17 | 154.9 (2) | C11—C12—C13—C14 | 0.5 (7) |
N1—P1—N3—C17 | 36.2 (3) | C12—C13—C14—C15 | −0.5 (7) |
O2—P1—N3—C16 | 64.9 (3) | C13—C14—C15—C10 | 1.0 (6) |
N2—P1—N3—C16 | −58.3 (3) | C11—C10—C15—C14 | −1.3 (5) |
N1—P1—N3—C16 | −177.0 (2) | C9—C10—C15—C14 | 175.6 (3) |
C6—C1—C2—C3 | 2.2 (5) | C16—N3—C17—C18 | −65.4 (3) |
C7—C1—C2—C3 | 179.4 (3) | P1—N3—C17—C18 | 82.3 (3) |
C1—C2—C3—C4 | −2.0 (5) | N3—C17—C18—C23 | −85.4 (4) |
C2—C3—C4—C5 | 0.5 (5) | N3—C17—C18—C19 | 93.4 (3) |
C2—C3—C4—Br1 | −179.1 (2) | C23—C18—C19—C20 | 0.2 (5) |
C3—C4—C5—C6 | 0.7 (6) | C17—C18—C19—C20 | −178.7 (3) |
Br1—C4—C5—C6 | −179.6 (3) | C18—C19—C20—C21 | −0.7 (6) |
C2—C1—C6—C5 | −0.9 (5) | C19—C20—C21—C22 | 1.2 (6) |
C7—C1—C6—C5 | −178.0 (3) | C20—C21—C22—C23 | −1.1 (6) |
C4—C5—C6—C1 | −0.5 (5) | C21—C22—C23—C18 | 0.5 (5) |
P1—N1—C7—O1 | −10.8 (5) | C19—C18—C23—C22 | −0.1 (5) |
P1—N1—C7—C1 | 169.7 (2) | C17—C18—C23—C22 | 178.8 (3) |
C6—C1—C7—O1 | 150.0 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2i | 0.86 | 1.99 | 2.845 (3) | 170.4 |
Symmetry code: (i) −x+2, −y+1, −z. |
Experimental details
Crystal data | |
Chemical formula | C23H25BrN3O2P |
Mr | 486.34 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 293 |
a, b, c (Å) | 9.0140 (4), 13.2690 (5), 19.377 (1) |
β (°) | 94.1500 (14) |
V (Å3) | 2311.54 (18) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.87 |
Crystal size (mm) | 0.11 × 0.09 × 0.08 |
Data collection | |
Diffractometer | Nonius KappaCCD diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12951, 5214, 2593 |
Rint | 0.051 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.053, 0.135, 1.00 |
No. of reflections | 5214 |
No. of parameters | 271 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.27, −0.62 |
Computer programs: COLLECT (Nonius, 1998), DENZO (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2i | 0.86 | 1.99 | 2.845 (3) | 170.4 |
Symmetry code: (i) −x+2, −y+1, −z. |
Acknowledgements
SD acknowledges the Alzahra University Research Council for partial support of this work.
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.
Carbacylamidophosphate compounds have attracted substantial interest for many years. These compounds have been employed in coordination chemistry as chelating reagents for various metal ions via their =P(O)N(H)C(O)- moiety (Trush et al., 2003; Gubina et al., 2000), as prodrugs in pharmacology and as pesticides in agriculture (Barak et al., 2000; Mallender et al., 2000). A thorough knowledge of the structural properties of these compounds should be beneficial for a detailed understanding of their pharmacological effects. The title compound, (I), was prepared by the reaction of (pBr-C6H5)C(O)NHP(O)(Cl)2 with two molecules of methylmenzyl amine.
The crystal structure of (I) reveals that, in the molecular core unit C(O)NHP(O), the C(O) and P(O) oxygen atoms are in anti-positions to each other. The phosphorus centre has a slightly distorted tetrahedral coordination, mainly due to the presence of the different substituents. The N3–P1–N1 angle (105.20 (12)°) is narrower than the ideal tetrahedral angle of 109.5, whereas the opposite O2–P1–N3 angle (119.05 (13)°) is wider than the ideal tetrahedral angle. The P1–O2 bond length (1.474 (2) Å) is in good agreement with P–O distances in other carbacylamidophosphates (Trush et al., 1999).
Examination of intermolecular distances indicates that the crystal structure of compound (I) consists of C9H13N2O2P units linked together via N—H···O hydrogen bonds into centrosymmetric dimers featuring eight-membered (OPNH)2 rings (Fig.2, Table 1).