N,N'-Dibenzyl-N''-(4-bromo-benzo-yl)-N,N'-dimethyl-phospho-ric triamide.

In the title compound, C(23)H(25)BrN(3)O(2)P, the P atom has a distorted tetra-hedral coordination. In the crystal structure, the mol-ecules 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 = 486.34

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.135

S = 1.00

5214 reflections

271 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.62 e Å−3

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.

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C23H25BrN3O2P	F000 = 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 = 1.0–27.5º
b = 13.2690 (5) Å	µ = 1.87 mm−1
c = 19.3770 (10) Å	T = 293 (2) K
β = 94.1500 (14)º	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
Monochromator: graphite	θmax = 27.5º
T = 293(2) K	θmin = 1.9º
π scans	h = −11→10
Absorption correction: none	k = −17→14
12951 measured reflections	l = −17→25
5214 independent reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.053	H-atom parameters constrained
wR(F2) = 0.135	w = 1/[σ2(Fo2) + (0.052P)2 + 0.3719P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max = 0.001
5214 reflections	Δρmax = 0.27 e Å−3
271 parameters	Δρmin = −0.62 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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

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) .