N,N′,N′′,N′′′-Tetrakis(2-methylphenyl)­oxybis(phospho­nic diamide): a redetermination at 150 K with Mo Kα radiation

Pourayoubi, M.; Padělková, Z.; Rostami Chaijan, M.; Růžička, A.

doi:10.1107/S1600536811002091

organic compounds

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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Pages o450-o451

doi:10.1107/S1600536811002091

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N,N′,N′′,N′′′-Tetrakis(2-methylphenyl)oxybis(phosphonic diamide): a redetermination at 150 K with Mo Kα radiation

Mehrdad Pourayoubi,^a ^* Zdeňka Padělková,^b Mahnaz Rostami Chaijan ^a and Aleš Růžička ^b

^aDepartment of Chemistry, Ferdowsi University of Mashhad, Mashhad, 91779, Iran, and ^bDepartment of General and Inorganic Chemistry, Faculty of Chemical Technology, University of Pardubice, Studentská 573, Pardubice 532 10, Czech Republic
^*Correspondence e-mail: mehrdad_pourayoubi@yahoo.com

(Received 22 December 2010; accepted 13 January 2011; online 22 January 2011)

The structure of the title compound, C₂₈H₃₂N₄O₃P₂, has been redetermined at 150 K, with much improved precision. The structure and molecular packing of the title compound was previously determined using Cu Kα radiation, with an R value of 0.0933 [Cameron et al. (1978 ). Z. Naturforsch. Teil B, 33, 728–730]. The c-axis length in this structure [13.8401 (8) Å] is almost half that reported in the original study. In the title compound, two (C₆H₄(2-CH₃)NH)₂P(O) units are bridged via an O atom [P—O—P = 133.31 (11)°]. The P atoms adopt a slightly distorted tetrahedral coordination geometry. In the crystal, molecules are linked via N—H⋯OP hydrogen bonds into extended chains parallel to the c axis. An intramolecular N—H⋯O=P hydrogen bond is also found in the molecule.

Related literature

For the previous determination of this structure, see: Cameron et al. (1978). For bond lengths and angles in related structures, see: Pourayoubi et al. (2010 ); Sabbaghi et al. (2010 ).

Experimental

Crystal data

C₂₈H₃₂N₄O₃P₂
M_r = 534.52
Monoclinic, P 2₁ /c
a = 14.2621 (6) Å
b = 15.7029 (11) Å
c = 13.8401 (8) Å
β = 118.915 (4)°
V = 2713.2 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 150 K
0.45 × 0.33 × 0.21 mm

Data collection

Bruker–Nonius KappaCCD area-detector diffractometer
Absorption correction: Gaussian integration (Coppens & Hamilton, 1970 ) T_min = 0.942, T_max = 0.969
19090 measured reflections
6133 independent reflections
4719 reflections with I > 2σ(I)
R_int = 0.047

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.121
S = 1.18
6133 reflections
334 parameters
H-atom parameters constrained
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.51 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N111—H111⋯O3ⁱ	0.86	2.16	2.926 (2)	149
N112—H112⋯O3	0.86	2.16	2.906 (2)	144
N113—H113⋯O2ⁱⁱ	0.86	1.97	2.814 (2)	167
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: COLLECT (Hooft, 1998 ) and DENZO (Otwinowski & Minor, 1997 ); cell refinement: COLLECT and DENZO; data reduction: COLLECT and DENZO; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and Mercury (Macrae et al., 2008 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811002091/sj5092sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811002091/sj5092Isup2.hkl

checkCIF report

Comment top

The structure and molecular packing of µ-oxo-bis(phosphenyl-o-toluidide) was previously reported at ambient temperature by Cameron et al. (1978) using 2595 independent reflections significantly above the background with Cu Kα radiation; R = 0.0933. The unit-cell length c and density were respectively reported as 25.26 (3) Å and 1.255 g cm^-3.

Here, we report on the low temperature X-ray determination of the title compound (Fig. 1) at 150 K using Mo Kα radiation, with some improved precision. The unit-cell length c (of 13.8401 (8) Å) and density (of 1.309 g cm^-3) in this structure are very different from the previously reported values.

In the title compound, two (C₆H₄(2-CH₃)NH)₂P(O) moieties are bridged via an oxygen atom (P1—O1—P2 angle = 133.31 (11)°); the P1—O1 and P2—O1 bond lengths of 1.6014 (16) and 1.6017 (16) Å are standard for the P—O—P moiety (Pourayoubi et al., 2010). The P atoms adopt a slightly distorted tetrahedral environment. The bond angles around the P atoms are in the range of 101.05 (9)° to 116.62 (11)° for P1 and 100.12 (10)° to 117.97 (11)° for P2.

The P1—O2 and P2—O3 bond lengths (1.4681 (17) and 1.4736 (17) Å) and the P—N bond lengths (1.630 (2), 1.6376 (19), 1.612 (2) and 1.634 (2) Å) are standard for this type of compound; for example in [4-H₃C—C₆H₄O]P(O)[NHC₆H₄-2-CH₃]₂ (Sabbaghi et al., 2010), P═O = 1.4692 (12) Å and P—N = 1.6268 (15) and 1.6279 (15) Å).

An intramolecular N–H···OP hydrogen bond (N···O = 2.906 (2) Å) is found between the oxygen atom of the P2 phosphoryl group and the N–H hydrogen atom of one of the amide moieties linked to the P1 atom. In the crystal structure, molecules are linked via N–H···OP hydrogen bonds (Fig. 2) into extended chains parallel to the c axis (N···O = 2.814 (2) & 2.926 (2) Å).

Related literature top

For the previous determination of this structure, see: Cameron et al. (1978). For bond lengths and angles in related structures, see: Pourayoubi et al. (2010); Sabbaghi et al. (2010).

Experimental top

To a solution of (11.42 mmol) phosphoryl chloride in chloroform (10 ml), a solution of o-toluidine (68.52 mmol) in chloroform (10 ml) was added dropwise at 268 K. After 4 h, the solvent was removed in vacuum. Single crystals were obtained from a mixture of chloroform/n-heptane after slow evaporation at room temperature. ³¹P{¹H} NMR (202.45 MHz, DMSO-d6, 300.0 K, H₃PO₄ external): -5.01 p.p.m. (s). ¹H NMR (500.13 MHz, DMSO-d6, 300.0 K, TMS): 2.03 (s, 12H, 4CH₃), 6.87–7.06 (m, 12H, Ar—H), 7.29 (m, 4H, Ar—H), 7.35 p.p.m. (d, ²J(P,H) = 7.9 Hz, 4H, NH). IR (KBr, cm^-1): 3746.3, 3413.2, 3300.4, 3188.5, 2927.3, 2854.8, 2358.8, 1675.8, 1599.4, 1496.1, 1402.5, 1226.5, 1111.8, 980.2, 844.9, 750.9.

Computing details top

Data collection: COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997); cell refinement: COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997); data reduction: COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure and atom labeling scheme for title compound with displacement ellipsoids at the 50% probability level.
	Fig. 2. A view of H-bonded chain in the crystal network of title compound. N–H···OP hydrogen bonds are shown as dashed lines.

N-{[bis(2-methylanilino)phosphoryloxy](2- methylanilino)phosphoryl]}-2-methylaniline top

Crystal data top

C₂₈H₃₂N₄O₃P₂	Z = 4
M_r = 534.52	F(000) = 1128
Monoclinic, P2₁/c	D_x = 1.309 Mg m⁻³
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 14.2621 (6) Å	θ = 1–27.5°
b = 15.7029 (11) Å	µ = 0.20 mm⁻¹
c = 13.8401 (8) Å	T = 150 K
β = 118.915 (4)°	Needle, colourless
V = 2713.2 (3) Å³	0.45 × 0.33 × 0.21 mm

Data collection top

Bruker–Nonius KappaCCD area-detector diffractometer	6133 independent reflections
Radiation source: fine-focus sealed tube	4719 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.047
Detector resolution: 9.091 pixels mm^-1	θ_max = 27.5°, θ_min = 1.6°
ϕ and ω scans to fill the Ewald sphere	h = −17→18
Absorption correction: integration Gaussian integration (Coppens & Hamilton, 1970)	k = −20→18
T_min = 0.942, T_max = 0.969	l = −17→17
19090 measured reflections

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.121	H-atom parameters constrained
S = 1.18	w = 1/[σ²(F_o²) + (0.026P)² + 3.5968P] where P = (F_o² + 2F_c²)/3
6133 reflections	(Δ/σ)_max < 0.001
334 parameters	Δρ_max = 0.38 e Å⁻³
0 restraints	Δρ_min = −0.51 e Å⁻³

Crystal data top

C₂₈H₃₂N₄O₃P₂	V = 2713.2 (3) Å³
M_r = 534.52	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.2621 (6) Å	µ = 0.20 mm⁻¹
b = 15.7029 (11) Å	T = 150 K
c = 13.8401 (8) Å	0.45 × 0.33 × 0.21 mm
β = 118.915 (4)°

Data collection top

Bruker–Nonius KappaCCD area-detector diffractometer	6133 independent reflections
Absorption correction: integration Gaussian integration (Coppens & Hamilton, 1970)	4719 reflections with I > 2σ(I)
T_min = 0.942, T_max = 0.969	R_int = 0.047
19090 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	0 restraints
wR(F²) = 0.121	H-atom parameters constrained
S = 1.18	Δρ_max = 0.38 e Å⁻³
6133 reflections	Δρ_min = −0.51 e Å⁻³
334 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
P1	0.71234 (5)	0.23508 (4)	0.23550 (5)	0.01571 (14)
P2	0.81104 (5)	0.21568 (4)	0.47636 (5)	0.01629 (14)
O3	0.71315 (13)	0.18618 (12)	0.47678 (13)	0.0220 (4)
O2	0.77228 (13)	0.18044 (11)	0.19840 (14)	0.0222 (4)
N111	0.67768 (15)	0.32469 (13)	0.16770 (15)	0.0171 (4)
H111	0.7047	0.3375	0.1258	0.021*
N112	0.60850 (15)	0.19217 (13)	0.23720 (15)	0.0181 (4)
H112	0.6126	0.1794	0.2995	0.022*
O1	0.78382 (12)	0.26154 (11)	0.36239 (12)	0.0195 (4)
N113	0.87451 (15)	0.28468 (13)	0.57247 (15)	0.0183 (4)
H113	0.8426	0.3037	0.6073	0.022*
N114	0.89635 (16)	0.14390 (13)	0.48176 (16)	0.0207 (4)
H114	0.9035	0.1363	0.4242	0.025*
C15	0.97931 (18)	0.31677 (16)	0.6050 (2)	0.0192 (5)
C8	0.51193 (18)	0.17513 (15)	0.13812 (18)	0.0171 (5)
C14	0.4100 (2)	0.25236 (18)	0.2194 (2)	0.0263 (6)
H14A	0.3375	0.2691	0.1963	0.032*
H14B	0.4543	0.3021	0.2366	0.032*
H14C	0.4356	0.2169	0.2837	0.032*
C10	0.3220 (2)	0.18702 (18)	0.0296 (2)	0.0268 (6)
H10	0.2563	0.2049	0.0211	0.032*
C27	0.9154 (2)	0.06277 (17)	0.6406 (2)	0.0259 (6)
H27	0.8443	0.0744	0.6200	0.031*
C23	1.0662 (2)	0.07556 (16)	0.6064 (2)	0.0231 (5)
C1	0.60452 (19)	0.38319 (15)	0.1753 (2)	0.0193 (5)
C2	0.5062 (2)	0.40163 (16)	0.0836 (2)	0.0226 (5)
C9	0.41430 (19)	0.20379 (16)	0.12797 (19)	0.0206 (5)
C24	1.1247 (2)	0.02480 (17)	0.6984 (2)	0.0294 (6)
H24	1.1947	0.0104	0.7174	0.035*
C21	1.0415 (2)	0.25452 (19)	0.7949 (2)	0.0297 (6)
H21A	1.1022	0.2605	0.8673	0.036*
H21B	1.0307	0.1954	0.7750	0.036*
H21C	0.9789	0.2768	0.7950	0.036*
C16	1.06130 (19)	0.30251 (16)	0.7133 (2)	0.0219 (5)
C6	0.6332 (2)	0.42124 (17)	0.2774 (2)	0.0267 (6)
H6	0.7003	0.4104	0.3374	0.032*
C22	0.9598 (2)	0.09322 (16)	0.5770 (2)	0.0214 (5)
C11	0.3249 (2)	0.1444 (2)	−0.0562 (2)	0.0326 (7)
H11	0.2619	0.1348	−0.1218	0.039*
C12	0.4213 (2)	0.11623 (19)	−0.0450 (2)	0.0305 (6)
H12	0.4234	0.0873	−0.1025	0.037*
C3	0.4368 (2)	0.45692 (18)	0.0985 (2)	0.0309 (6)
H3	0.3708	0.4705	0.0386	0.037*
C13	0.5154 (2)	0.13111 (17)	0.0530 (2)	0.0241 (5)
H13	0.5806	0.1117	0.0615	0.029*
C25	1.0816 (2)	−0.00486 (18)	0.7628 (2)	0.0327 (6)
H25	1.1228	−0.0381	0.8247	0.039*
C19	1.1003 (2)	0.39397 (19)	0.5620 (3)	0.0331 (6)
H19	1.1132	0.4239	0.5116	0.040*
C7	0.4739 (2)	0.36301 (18)	−0.0263 (2)	0.0264 (6)
H7A	0.5312	0.3690	−0.0435	0.032*
H7B	0.4112	0.3914	−0.0816	0.032*
H7C	0.4585	0.3037	−0.0247	0.032*
C20	0.9989 (2)	0.36202 (18)	0.5309 (2)	0.0261 (6)
H20	0.9437	0.3714	0.4595	0.031*
C26	0.9776 (2)	0.01502 (17)	0.7348 (2)	0.0300 (6)
H26	0.9489	−0.0035	0.7788	0.036*
C28	1.1164 (2)	0.11288 (19)	0.5422 (2)	0.0308 (6)
H28A	1.1902	0.0960	0.5754	0.037*
H28B	1.1120	0.1739	0.5429	0.037*
H28C	1.0791	0.0928	0.4674	0.037*
C18	1.1820 (2)	0.3807 (2)	0.6680 (3)	0.0354 (7)
H18	1.2501	0.4021	0.6897	0.043*
C5	0.5626 (3)	0.47486 (18)	0.2898 (3)	0.0347 (7)
H5	0.5812	0.4991	0.3581	0.042*
C17	1.1622 (2)	0.33534 (19)	0.7422 (2)	0.0314 (6)
H17	1.2181	0.3266	0.8133	0.038*
C4	0.4648 (2)	0.49159 (18)	0.2005 (3)	0.0344 (7)
H4	0.4168	0.5270	0.2087	0.041*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P1	0.0135 (3)	0.0217 (3)	0.0119 (3)	0.0002 (2)	0.0062 (2)	0.0018 (2)
P2	0.0149 (3)	0.0225 (3)	0.0113 (3)	−0.0025 (2)	0.0062 (2)	0.0001 (2)
O3	0.0189 (8)	0.0333 (10)	0.0141 (8)	−0.0056 (8)	0.0083 (7)	−0.0009 (7)
O2	0.0214 (8)	0.0264 (9)	0.0232 (9)	0.0059 (7)	0.0144 (7)	0.0043 (7)
N111	0.0195 (9)	0.0215 (10)	0.0146 (9)	−0.0007 (8)	0.0115 (8)	0.0009 (8)
N112	0.0163 (9)	0.0267 (11)	0.0119 (9)	−0.0035 (8)	0.0073 (8)	0.0021 (8)
O1	0.0163 (8)	0.0280 (9)	0.0113 (7)	−0.0049 (7)	0.0045 (6)	0.0020 (7)
N113	0.0150 (9)	0.0261 (11)	0.0150 (9)	−0.0024 (8)	0.0081 (8)	−0.0046 (8)
N114	0.0260 (11)	0.0239 (11)	0.0148 (9)	0.0019 (9)	0.0119 (8)	0.0005 (8)
C15	0.0151 (11)	0.0206 (12)	0.0221 (12)	−0.0010 (10)	0.0090 (9)	−0.0053 (10)
C8	0.0178 (11)	0.0167 (11)	0.0140 (10)	−0.0019 (9)	0.0055 (9)	0.0029 (9)
C14	0.0216 (12)	0.0355 (15)	0.0246 (13)	0.0017 (11)	0.0134 (10)	0.0018 (11)
C10	0.0167 (12)	0.0343 (15)	0.0249 (13)	−0.0031 (11)	0.0063 (10)	0.0033 (11)
C27	0.0308 (14)	0.0234 (13)	0.0265 (13)	0.0003 (11)	0.0163 (11)	0.0009 (11)
C23	0.0253 (13)	0.0198 (13)	0.0237 (12)	−0.0030 (10)	0.0115 (11)	−0.0085 (10)
C1	0.0245 (12)	0.0156 (11)	0.0247 (12)	−0.0012 (10)	0.0172 (10)	0.0011 (10)
C2	0.0249 (12)	0.0182 (12)	0.0280 (13)	0.0002 (10)	0.0154 (11)	0.0044 (10)
C9	0.0206 (12)	0.0228 (13)	0.0182 (11)	−0.0031 (10)	0.0092 (10)	0.0030 (10)
C24	0.0285 (14)	0.0237 (14)	0.0276 (14)	0.0045 (11)	0.0068 (11)	−0.0027 (11)
C21	0.0266 (13)	0.0372 (16)	0.0179 (12)	−0.0018 (12)	0.0049 (10)	−0.0012 (11)
C16	0.0172 (11)	0.0228 (13)	0.0227 (12)	0.0026 (10)	0.0072 (10)	−0.0052 (10)
C6	0.0338 (14)	0.0227 (13)	0.0274 (13)	−0.0032 (12)	0.0178 (12)	−0.0040 (11)
C22	0.0265 (13)	0.0183 (12)	0.0184 (11)	−0.0008 (10)	0.0101 (10)	−0.0029 (10)
C11	0.0237 (13)	0.0411 (17)	0.0192 (12)	−0.0111 (13)	−0.0007 (10)	−0.0013 (12)
C12	0.0367 (15)	0.0334 (15)	0.0184 (12)	−0.0098 (13)	0.0109 (11)	−0.0079 (11)
C3	0.0314 (14)	0.0262 (15)	0.0383 (15)	0.0041 (12)	0.0193 (13)	0.0078 (12)
C13	0.0246 (13)	0.0260 (14)	0.0210 (12)	−0.0015 (11)	0.0104 (10)	−0.0014 (10)
C25	0.0423 (16)	0.0217 (14)	0.0250 (13)	0.0037 (12)	0.0090 (12)	0.0032 (11)
C19	0.0330 (15)	0.0341 (16)	0.0426 (16)	−0.0031 (13)	0.0264 (14)	0.0005 (13)
C7	0.0255 (13)	0.0281 (14)	0.0241 (13)	0.0016 (11)	0.0107 (11)	0.0038 (11)
C20	0.0244 (13)	0.0295 (14)	0.0257 (13)	−0.0042 (11)	0.0130 (11)	−0.0025 (11)
C26	0.0429 (16)	0.0222 (13)	0.0267 (14)	−0.0017 (12)	0.0182 (13)	0.0024 (11)
C28	0.0271 (14)	0.0330 (15)	0.0343 (15)	−0.0002 (12)	0.0164 (12)	−0.0020 (12)
C18	0.0222 (13)	0.0353 (16)	0.0519 (18)	−0.0066 (12)	0.0203 (13)	−0.0101 (14)
C5	0.0517 (18)	0.0266 (15)	0.0364 (16)	−0.0027 (14)	0.0297 (15)	−0.0062 (12)
C17	0.0177 (12)	0.0350 (16)	0.0341 (15)	0.0005 (12)	0.0066 (11)	−0.0063 (12)
C4	0.0455 (17)	0.0195 (14)	0.0502 (18)	0.0071 (13)	0.0327 (15)	0.0024 (13)

Geometric parameters (Å, º) top

P1—O2	1.4681 (17)	C2—C7	1.489 (4)
P1—O1	1.6014 (16)	C24—C25	1.385 (4)
P1—N111	1.630 (2)	C24—H24	0.9300
P1—N112	1.6376 (19)	C21—C16	1.494 (4)
P2—O3	1.4736 (17)	C21—H21A	0.9601
P2—O1	1.6017 (16)	C21—H21B	0.9599
P2—N113	1.612 (2)	C21—H21C	0.9601
P2—N114	1.634 (2)	C16—C17	1.392 (4)
N111—C1	1.432 (3)	C6—C5	1.385 (4)
N111—H111	0.8600	C6—H6	0.9300
N112—C8	1.422 (3)	C11—C12	1.379 (4)
N112—H112	0.8599	C11—H11	0.9299
N113—C15	1.428 (3)	C12—C13	1.391 (4)
N113—H113	0.8600	C12—H12	0.9300
N114—C22	1.427 (3)	C3—C4	1.380 (4)
N114—H114	0.8600	C3—H3	0.9299
C15—C20	1.383 (4)	C13—H13	0.9300
C15—C16	1.403 (3)	C25—C26	1.375 (4)
C8—C13	1.387 (3)	C25—H25	0.9300
C8—C9	1.404 (3)	C19—C18	1.379 (4)
C14—C9	1.504 (3)	C19—C20	1.388 (4)
C14—H14A	0.9600	C19—H19	0.9300
C14—H14B	0.9600	C7—H7A	0.9601
C14—H14C	0.9599	C7—H7B	0.9600
C10—C11	1.382 (4)	C7—H7C	0.9601
C10—C9	1.387 (3)	C20—H20	0.9301
C10—H10	0.9300	C26—H26	0.9300
C27—C26	1.389 (4)	C28—H28A	0.9601
C27—C22	1.393 (4)	C28—H28B	0.9600
C27—H27	0.9300	C28—H28C	0.9600
C23—C24	1.388 (4)	C18—C17	1.386 (4)
C23—C22	1.396 (3)	C18—H18	0.9300
C23—C28	1.504 (4)	C5—C4	1.369 (4)
C1—C2	1.393 (3)	C5—H5	0.9300
C1—C6	1.401 (3)	C17—H17	0.9300
C2—C3	1.404 (4)	C4—H4	0.9300

O2—P1—O1	111.45 (10)	C16—C21—H21C	109.4
O2—P1—N111	111.65 (10)	H21A—C21—H21C	109.5
O1—P1—N111	105.22 (10)	H21B—C21—H21C	109.5
O2—P1—N112	116.62 (11)	C17—C16—C15	117.3 (2)
O1—P1—N112	101.05 (9)	C17—C16—C21	121.1 (2)
N111—P1—N112	109.81 (10)	C15—C16—C21	121.6 (2)
O3—P2—O1	111.48 (9)	C5—C6—C1	120.6 (3)
O3—P2—N113	111.30 (10)	C5—C6—H6	119.7
O1—P2—N113	106.40 (10)	C1—C6—H6	119.7
O3—P2—N114	117.97 (11)	C27—C22—C23	120.6 (2)
O1—P2—N114	100.12 (10)	C27—C22—N114	119.8 (2)
N113—P2—N114	108.51 (11)	C23—C22—N114	119.6 (2)
C1—N111—P1	122.72 (15)	C12—C11—C10	120.1 (2)
C1—N111—H111	118.7	C12—C11—H11	119.9
P1—N111—H111	118.6	C10—C11—H11	120.0
C8—N112—P1	121.64 (15)	C11—C12—C13	119.7 (3)
C8—N112—H112	119.2	C11—C12—H12	120.2
P1—N112—H112	119.2	C13—C12—H12	120.2
P1—O1—P2	133.31 (11)	C4—C3—C2	121.2 (3)
C15—N113—P2	125.59 (16)	C4—C3—H3	119.3
C15—N113—H113	117.2	C2—C3—H3	119.5
P2—N113—H113	117.2	C8—C13—C12	119.9 (2)
C22—N114—P2	123.54 (17)	C8—C13—H13	120.0
C22—N114—H114	118.2	C12—C13—H13	120.1
P2—N114—H114	118.3	C26—C25—C24	119.7 (3)
C20—C15—C16	120.8 (2)	C26—C25—H25	120.2
C20—C15—N113	120.2 (2)	C24—C25—H25	120.1
C16—C15—N113	119.0 (2)	C18—C19—C20	119.5 (3)
C13—C8—C9	121.0 (2)	C18—C19—H19	120.2
C13—C8—N112	119.8 (2)	C20—C19—H19	120.3
C9—C8—N112	119.2 (2)	C2—C7—H7A	109.5
C9—C14—H14A	109.5	C2—C7—H7B	109.5
C9—C14—H14B	109.4	H7A—C7—H7B	109.5
H14A—C14—H14B	109.5	C2—C7—H7C	109.4
C9—C14—H14C	109.5	H7A—C7—H7C	109.5
H14A—C14—H14C	109.5	H7B—C7—H7C	109.5
H14B—C14—H14C	109.5	C15—C20—C19	120.6 (3)
C11—C10—C9	121.8 (2)	C15—C20—H20	119.8
C11—C10—H10	119.1	C19—C20—H20	119.5
C9—C10—H10	119.1	C25—C26—C27	120.0 (3)
C26—C27—C22	119.9 (3)	C25—C26—H26	120.0
C26—C27—H27	120.1	C27—C26—H26	120.0
C22—C27—H27	120.0	C23—C28—H28A	109.6
C24—C23—C22	117.9 (2)	C23—C28—H28B	109.3
C24—C23—C28	121.3 (2)	H28A—C28—H28B	109.5
C22—C23—C28	120.8 (2)	C23—C28—H28C	109.5
C2—C1—C6	120.3 (2)	H28A—C28—H28C	109.5
C2—C1—N111	121.0 (2)	H28B—C28—H28C	109.5
C6—C1—N111	118.7 (2)	C19—C18—C17	119.8 (3)
C1—C2—C3	117.8 (2)	C19—C18—H18	120.0
C1—C2—C7	121.6 (2)	C17—C18—H18	120.1
C3—C2—C7	120.6 (2)	C4—C5—C6	119.2 (3)
C10—C9—C8	117.5 (2)	C4—C5—H5	120.3
C10—C9—C14	121.1 (2)	C6—C5—H5	120.5
C8—C9—C14	121.3 (2)	C18—C17—C16	122.0 (3)
C25—C24—C23	121.8 (3)	C18—C17—H17	118.8
C25—C24—H24	119.2	C16—C17—H17	119.2
C23—C24—H24	119.0	C5—C4—C3	120.8 (3)
C16—C21—H21A	109.5	C5—C4—H4	119.5
C16—C21—H21B	109.4	C3—C4—H4	119.6
H21A—C21—H21B	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N111—H111···O3ⁱ	0.86	2.16	2.926 (2)	149
N112—H112···O3	0.86	2.16	2.906 (2)	144
N113—H113···O2ⁱⁱ	0.86	1.97	2.814 (2)	167

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) x, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₈H₃₂N₄O₃P₂
M_r	534.52
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	150
a, b, c (Å)	14.2621 (6), 15.7029 (11), 13.8401 (8)
β (°)	118.915 (4)
V (Å³)	2713.2 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.45 × 0.33 × 0.21

Data collection
Diffractometer	Bruker–Nonius KappaCCD area-detector diffractometer
Absorption correction	Integration Gaussian integration (Coppens & Hamilton, 1970)
T_min, T_max	0.942, 0.969
No. of measured, independent and observed [I > 2σ(I)] reflections	19090, 6133, 4719
R_int	0.047
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.121, 1.18
No. of reflections	6133
No. of parameters	334
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.51

Computer programs: COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N111—H111···O3ⁱ	0.86	2.16	2.926 (2)	149
N112—H112···O3	0.86	2.16	2.906 (2)	144
N113—H113···O2ⁱⁱ	0.86	1.97	2.814 (2)	167

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) x, −y+1/2, z+1/2.

Acknowledgements

The authors wish to thank the Ministry of Education of the Czech Republic for the Research University Grant (project No. VZ0021627501). Partial support of this work by Ferdowsi University of Mashhad is gratefully acknowledged.

References

Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. CrossRef Web of Science IUCr Journals Google Scholar
Cameron, T. S., Cordes, R. E. & Jackman, F. A. (1978). Z. Naturforsch. Teil B, 33, 728–730. Google Scholar
Coppens, P. & Hamilton, W. C. (1970). Acta Cryst. A26, 71–83. CrossRef IUCr Journals Web of Science Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Hooft, R. W. W. (1998). COLLECT. Nonius BV, Delft, The Netherlands. Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CrossRef CAS IUCr Journals Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Pourayoubi, M., Ghadimi, S. & Ebrahimi Valmoozi, A. A. (2010). Acta Cryst. E66, o450. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sabbaghi, F., Mancilla Percino, T., Pourayoubi, M. & Leyva, M. A. (2010). Acta Cryst. E66, o1755. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 67| Part 2| February 2011| Pages o450-o451

doi:10.1107/S1600536811002091

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

N,N′,N′′,N′′′-Tetra­kis­(2-methylphenyl)­oxybis(phospho­nic di­amide): a redetermination at 150 K with Mo Kα radiation

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

N,N′,N′′,N′′′-Tetrakis(2-methylphenyl)oxybis(phosphonic diamide): a redetermination at 150 K with Mo Kα radiation