Tetra-phenyl piperazine-1,4-diyldiphos-pho-nate.

The mol-ecule of the title compound, C(28)H(28)N(2)O(6)P(2), is organized around an inversion center located at the centre of the piperazine ring. Both piperazine N atoms are substituted by P(O)(OC(6)H(5))(2) phospho-ester groups. The P atoms display a slightly distorted tetra-hedral environment; the N atoms show some deviation from planarity. The O atoms of the P=O groups are involved in inter-molecular C-H⋯O hydrogen bonds, building R(2) (2)(22) rings, in extended chains parallel to the a axis. C-H⋯π inter-actions involving the phenyl rings further stabilize the packing.

Related literature

For the physical properties of bis­phospho­ramidates, see: Nguyen & Kim (2008 ▶). For related structures, see: Chen et al. (2007 ▶); Balakrishna et al. (2003 ▶, 2006 ▶); Rodriguez i Zubiri et al. (2002 ▶). For hydrogen-bond motifs, see: Etter et al. (1990 ▶); Bernstein et al. (1995 ▶).

Experimental

Crystal data

C28H28N2O6P2

M = 550.46

Monoclinic,

a = 6.3117 (4) Å

b = 8.9530 (5) Å

c = 22.8630 (13) Å

β = 96.756 (1)°

V = 1282.99 (13) Å3

Z = 2

Mo Kα radiation

μ = 0.22 mm−1

T = 100 K

0.55 × 0.40 × 0.20 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.890, T max = 0.958

14864 measured reflections

3405 independent reflections

3071 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.089

S = 1.03

3405 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.51 e Å−3

Δρmin = −0.27 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶), ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810047860/dn2623sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810047860/dn2623Isup2.hkl

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

C28H28N2O6P2	F(000) = 576
Mr = 550.46	Dx = 1.425 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2258 reflections
a = 6.3117 (4) Å	θ = 3–29°
b = 8.9530 (5) Å	µ = 0.22 mm−1
c = 22.8630 (13) Å	T = 100 K
β = 96.756 (1)°	Plate, colourless
V = 1282.99 (13) Å3	0.55 × 0.40 × 0.20 mm
Z = 2

Bruker APEXII CCD area-detector diffractometer	3405 independent reflections
Radiation source: fine-focus sealed tube	3071 reflections with I > 2σ(I)
graphite	Rint = 0.025
ω scans	θmax = 29.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −8→8
Tmin = 0.890, Tmax = 0.958	k = −12→12
14864 measured reflections	l = −30→31

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.089	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0496P)2 + 0.567P] where P = (Fo2 + 2Fc2)/3
3405 reflections	(Δ/σ)max = 0.002
172 parameters	Δρmax = 0.51 e Å−3
0 restraints	Δρmin = −0.27 e Å−3

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
P1	0.29408 (4)	0.70141 (3)	0.584588 (12)	0.01226 (9)
O1	0.08499 (13)	0.65211 (10)	0.59873 (4)	0.01722 (18)
O2	0.30060 (14)	0.86102 (9)	0.55434 (4)	0.01595 (17)
O3	0.46851 (13)	0.72855 (9)	0.63989 (3)	0.01431 (17)
N1	0.40456 (15)	0.59125 (11)	0.54033 (4)	0.01435 (19)
C1	0.27230 (18)	0.49056 (13)	0.50046 (5)	0.0154 (2)
H1A	0.2168	0.5452	0.4642	0.019*
H1B	0.1490	0.4557	0.5198	0.019*
C2	0.59794 (18)	0.64262 (13)	0.51554 (5)	0.0159 (2)
H2A	0.6852	0.7054	0.5448	0.019*
H2B	0.5564	0.7039	0.4800	0.019*
C3	0.24646 (19)	0.99346 (12)	0.58193 (5)	0.0141 (2)
C4	0.03688 (19)	1.04226 (13)	0.57405 (5)	0.0174 (2)
H4A	−0.0717	0.9831	0.5531	0.021*
C5	−0.0111 (2)	1.18012 (14)	0.59758 (6)	0.0213 (2)
H5A	−0.1538	1.2157	0.5925	0.026*
C6	0.1478 (2)	1.26566 (14)	0.62831 (6)	0.0224 (3)
H6A	0.1142	1.3603	0.6436	0.027*
C7	0.3561 (2)	1.21302 (14)	0.63680 (6)	0.0221 (3)
H7A	0.4642	1.2709	0.6586	0.026*
C8	0.40715 (19)	1.07579 (14)	0.61346 (5)	0.0181 (2)
H8A	0.5494	1.0393	0.6191	0.022*
C9	0.51165 (18)	0.61794 (12)	0.68335 (5)	0.0136 (2)
C10	0.36396 (19)	0.58904 (13)	0.72215 (5)	0.0160 (2)
H10A	0.2295	0.6380	0.7181	0.019*
C11	0.4174 (2)	0.48638 (14)	0.76736 (5)	0.0190 (2)
H11A	0.3176	0.4638	0.7941	0.023*
C12	0.6154 (2)	0.41695 (14)	0.77356 (5)	0.0203 (2)
H12A	0.6518	0.3486	0.8049	0.024*
C13	0.7607 (2)	0.44750 (14)	0.73384 (6)	0.0204 (2)
H13A	0.8957	0.3993	0.7380	0.025*
C14	0.70950 (18)	0.54823 (13)	0.68798 (5)	0.0168 (2)
H14A	0.8075	0.5688	0.6605	0.020*

	U11	U22	U33	U12	U13	U23
P1	0.01325 (14)	0.01125 (14)	0.01239 (14)	0.00080 (10)	0.00199 (10)	−0.00088 (9)
O1	0.0147 (4)	0.0193 (4)	0.0182 (4)	0.0001 (3)	0.0038 (3)	−0.0014 (3)
O2	0.0226 (4)	0.0125 (4)	0.0133 (4)	0.0031 (3)	0.0041 (3)	−0.0003 (3)
O3	0.0169 (4)	0.0121 (4)	0.0136 (4)	−0.0012 (3)	−0.0001 (3)	0.0006 (3)
N1	0.0137 (4)	0.0127 (4)	0.0170 (5)	−0.0015 (3)	0.0031 (3)	−0.0035 (3)
C1	0.0135 (5)	0.0158 (5)	0.0170 (5)	−0.0008 (4)	0.0017 (4)	−0.0036 (4)
C2	0.0165 (5)	0.0133 (5)	0.0187 (5)	−0.0013 (4)	0.0054 (4)	−0.0029 (4)
C3	0.0207 (5)	0.0103 (5)	0.0116 (5)	0.0014 (4)	0.0039 (4)	0.0008 (4)
C4	0.0195 (5)	0.0157 (5)	0.0166 (5)	0.0005 (4)	0.0005 (4)	0.0003 (4)
C5	0.0238 (6)	0.0170 (6)	0.0240 (6)	0.0060 (5)	0.0065 (5)	0.0036 (5)
C6	0.0344 (7)	0.0118 (5)	0.0229 (6)	0.0006 (5)	0.0112 (5)	−0.0009 (4)
C7	0.0290 (6)	0.0170 (6)	0.0206 (6)	−0.0073 (5)	0.0049 (5)	−0.0026 (4)
C8	0.0191 (5)	0.0177 (6)	0.0179 (5)	−0.0020 (4)	0.0033 (4)	0.0012 (4)
C9	0.0165 (5)	0.0107 (5)	0.0130 (5)	−0.0004 (4)	−0.0004 (4)	−0.0008 (4)
C10	0.0174 (5)	0.0157 (5)	0.0150 (5)	0.0024 (4)	0.0027 (4)	−0.0012 (4)
C11	0.0249 (6)	0.0178 (5)	0.0148 (5)	0.0005 (5)	0.0045 (4)	0.0005 (4)
C12	0.0268 (6)	0.0166 (6)	0.0167 (5)	0.0024 (5)	−0.0011 (5)	0.0019 (4)
C13	0.0181 (5)	0.0180 (6)	0.0245 (6)	0.0037 (4)	−0.0006 (5)	−0.0001 (5)
C14	0.0154 (5)	0.0157 (5)	0.0195 (5)	0.0000 (4)	0.0021 (4)	−0.0016 (4)

P1—O1	1.4633 (9)	C5—C6	1.3855 (19)
P1—O2	1.5901 (9)	C5—H5A	0.9500
P1—O3	1.5944 (8)	C6—C7	1.3885 (19)
P1—N1	1.6275 (10)	C6—H6A	0.9500
O2—C3	1.4040 (13)	C7—C8	1.3923 (17)
O3—C9	1.4066 (13)	C7—H7A	0.9500
N1—C1	1.4702 (14)	C8—H8A	0.9500
N1—C2	1.4783 (14)	C9—C10	1.3847 (16)
C1—C2i	1.5155 (16)	C9—C14	1.3889 (16)
C1—H1A	0.9900	C10—C11	1.3946 (16)
C1—H1B	0.9900	C10—H10A	0.9500
C2—C1i	1.5155 (16)	C11—C12	1.3880 (18)
C2—H2A	0.9900	C11—H11A	0.9500
C2—H2B	0.9900	C12—C13	1.3913 (18)
C3—C4	1.3846 (16)	C12—H12A	0.9500
C3—C8	1.3855 (17)	C13—C14	1.3919 (17)
C4—C5	1.3937 (17)	C13—H13A	0.9500
C4—H4A	0.9500	C14—H14A	0.9500
O1—P1—O2	115.93 (5)	C6—C5—H5A	119.7
O1—P1—O3	115.30 (5)	C4—C5—H5A	119.7
O2—P1—O3	99.04 (4)	C5—C6—C7	120.00 (11)
O1—P1—N1	114.71 (5)	C5—C6—H6A	120.0
O2—P1—N1	103.85 (5)	C7—C6—H6A	120.0
O3—P1—N1	106.20 (5)	C6—C7—C8	120.27 (12)
C3—O2—P1	122.92 (7)	C6—C7—H7A	119.9
C9—O3—P1	120.74 (7)	C8—C7—H7A	119.9
C1—N1—C2	112.78 (9)	C3—C8—C7	118.71 (11)
C1—N1—P1	120.23 (8)	C3—C8—H8A	120.6
C2—N1—P1	118.91 (7)	C7—C8—H8A	120.6
N1—C1—C2i	110.39 (9)	C10—C9—C14	122.29 (11)
N1—C1—H1A	109.6	C10—C9—O3	119.68 (10)
C2i—C1—H1A	109.6	C14—C9—O3	117.89 (10)
N1—C1—H1B	109.6	C9—C10—C11	118.39 (11)
C2i—C1—H1B	109.6	C9—C10—H10A	120.8
H1A—C1—H1B	108.1	C11—C10—H10A	120.8
N1—C2—C1i	109.99 (9)	C12—C11—C10	120.49 (11)
N1—C2—H2A	109.7	C12—C11—H11A	119.8
C1i—C2—H2A	109.7	C10—C11—H11A	119.8
N1—C2—H2B	109.7	C11—C12—C13	119.99 (11)
C1i—C2—H2B	109.7	C11—C12—H12A	120.0
H2A—C2—H2B	108.2	C13—C12—H12A	120.0
C4—C3—C8	121.97 (11)	C12—C13—C14	120.44 (11)
C4—C3—O2	119.17 (10)	C12—C13—H13A	119.8
C8—C3—O2	118.76 (10)	C14—C13—H13A	119.8
C3—C4—C5	118.47 (11)	C9—C14—C13	118.39 (11)
C3—C4—H4A	120.8	C9—C14—H14A	120.8
C5—C4—H4A	120.8	C13—C14—H14A	120.8
C6—C5—C4	120.55 (12)

Cg1 and Cg2 are the centroids of the C3–C8 and C11–C14 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14A···O1ii	0.95	2.49	3.4327 (15)	172
C11—H11A···Cg1iii	0.95	2.74	3.3324 (12)	121
C7—H7A···Cg2iv	0.95	2.59	3.4099 (13)	145

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C3–C8 and C11–C14 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14A⋯O1i	0.95	2.49	3.4327 (15)	172
C11—H11A⋯Cg1ii	0.95	2.74	3.3324 (12)	121
C7—H7A⋯Cg2iii	0.95	2.59	3.4099 (13)	145

Symmetry codes: (i) ; (ii) ; (iii) .