N,N′-Dibenzyl-N′′-(4-bromo­benzo­yl)-N,N′-dimethyl­phospho­ric triamide

Dehghanpour, S.; Welter, R.; Barry, A.H.; Tabasi, F.

doi:10.1107/S1600536808004777

organic compounds

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ISSN: 2056-9890

Volume 64| Part 3| March 2008| Page o633

doi:10.1107/S1600536808004777

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N,N′-Dibenzyl-N′′-(4-bromobenzoyl)-N,N′-dimethylphosphoric triamide

Saeed Dehghanpour,^a ^* Richard Welter,^b Aliou Hamady Barry ^c and Farzaneh Tabasi ^a

^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

(Received 9 January 2008; accepted 19 February 2008; online 27 February 2008)

In the title compound, C₂₃H₂₅BrN₃O₂P, the P atom has a distorted tetrahedral coordination. In the crystal structure, 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

C₂₃H₂₅BrN₃O₂P
M_r = 486.34
Monoclinic, P 2₁ /n
a = 9.0140 (4) Å
b = 13.2690 (5) Å
c = 19.377 (1) Å
β = 94.1500 (14)°
V = 2311.54 (18) Å³
Z = 4
Mo Kα radiation
μ = 1.87 mm⁻¹
T = 293 (2) K
0.11 × 0.09 × 0.08 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: none
12951 measured reflections
5214 independent reflections
2593 reflections with I > 2σ(I)
R_int = 0.051

Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.135
S = 1.00
5214 reflections
271 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.62 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2ⁱ	0.86	1.99	2.845 (3)	170
Symmetry code: (i) -x+2, -y+1, -z.

Data collection: COLLECT (Nonius, 1998 ); cell refinement: 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

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808004777/zl2095sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808004777/zl2095Isup2.hkl

checkCIF report

Comment top

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).

Related literature top

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 top

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%.

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: 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).

Figures top

	Fig. 1. Molecular structure of I showing the atom-labelling scheme with thermal ellipsoids drawn at the 50% probability level.
	Fig. 2. Representation of the hydrogen bonds in the structure of (I). For clarity, only the O2 atom in the second molecule is labeled (O2ⁱ), Symmetry code i: 2 - x, 1 - y, -z.

N,N'-Dibenzyl-N''-(4-bromobenzoyl)- N,N'-dimethylphosphoric triamide top

Crystal data top

C₂₃H₂₅BrN₃O₂P	F(000) = 1000
M_r = 486.34	D_x = 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

Data collection top

Nonius KappaCCD diffractometer	2593 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.051
Graphite monochromator	θ_max = 27.5°, θ_min = 1.9°
π scans	h = −11→10
12951 measured reflections	k = −17→14
5214 independent reflections	l = −17→25

Refinement top

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(F_o²) + (0.052P)² + 0.3719P] where P = (F_o² + 2F_c²)/3
5214 reflections	(Δ/σ)_max = 0.001
271 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.62 e Å⁻³

Crystal data top

C₂₃H₂₅BrN₃O₂P	V = 2311.54 (18) Å³
M_r = 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)°

Data collection top

Nonius KappaCCD diffractometer	2593 reflections with I > 2σ(I)
12951 measured reflections	R_int = 0.051
5214 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.135	H-atom parameters constrained
S = 1.00	Δρ_max = 0.27 e Å⁻³
5214 reflections	Δρ_min = −0.62 e Å⁻³
271 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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
M_r	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
R_int	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
Δρ_max, Δρ_min (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).

Hydrogen-bond geometry (Å, º) top

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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