N,N′-Dibenzyl-N,N′-dimethyl-N′′-(4-nitro­benzo­yl)phospho­ric triamide

Pourayoubi, M.; Rostami Chaijan, M.; Torre-Fernández, L.; García-Granda, S.

doi:10.1107/S1600536811011275

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 5| May 2011| Page o1031

doi:10.1107/S1600536811011275

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N,N′-Dibenzyl-N,N′-dimethyl-N′′-(4-nitrobenzoyl)phosphoric triamide

Mehrdad Pourayoubi,^a Mahnaz Rostami Chaijan,^a Laura Torre-Fernández ^b and Santiago García-Granda ^b ^*

^aDepartment of Chemistry, Ferdowsi University of Mashhad, Mashhad, 91779, Iran, and ^bDepartamento de Química Física y Analítica, Facultad de Química, Universidad de Oviedo - CINN C/ Julián Clavería, 8, 33006 Oviedo (Asturias) Spain
^*Correspondence e-mail: sgg@uniovi.es

(Received 22 March 2011; accepted 26 March 2011; online 7 April 2011)

The P atom in the title compound, C₂₃H₂₅N₄O₄P, is in a slightly distorted tetrahedral coordination environment and the N atoms show sp² character. The phosphoryl group and the NH unit are syn with respect to each other. In the crystal, pairs of intermolecular N—H⋯O(P) hydrogen bonds form centrosymmetric dimers.

Related literature

For phosphorus compounds with general formula XP(O)[N(CH₃)(CH₂C₆H₅)]₂, see: Gholivand et al. (2005 ). For bond lengths in a related structure, see: Sabbaghi et al. (2010 ). For hydrogen-bond motifs, see: Etter et al. (1990 ); Bernstein et al. (1995 ).

Experimental

Crystal data

C₂₃H₂₅N₄O₄P
M_r = 452.44
Triclinic, $[P \overline 1]$
a = 8.3526 (5) Å
b = 11.8150 (5) Å
c = 12.2668 (4) Å
α = 77.184 (3)°
β = 81.289 (4)°
γ = 71.928 (4)°
V = 1117.70 (9) Å³
Z = 2
Cu Kα radiation
μ = 1.41 mm⁻¹
T = 297 K
0.24 × 0.14 × 0.05 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.941, T_max = 1.000
8669 measured reflections
4203 independent reflections
3779 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.093
S = 1.05
4203 reflections
390 parameters
All H-atom parameters refined
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N8—H8⋯O2ⁱ	0.85 (2)	2.07 (2)	2.909 (2)	169 (2)
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR2004 (Burla et al., 2005 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: Mercury (Macrae et al., 2008 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811011275/ng5139sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811011275/ng5139Isup2.hkl

checkCIF report

Comment top

Some phosphoric triamide compounds of the general formula XP(O)[N(CH₃)(CH₂C₆H₅)]₂ [X = Cl, C₆H₅C(O)NH & CCl₃C(O)NH (Gholivand et al., 2005) have been structurally investigated. Here, we report on the synthesis and crystal structure of title compound (where X = 4-NO₂C₆H₄C(O)NH).

The asymmetric unit consists of a single molecule, shown in Fig. 1, of the title compound with no unusual bonding features. The P═O and P—N bond lengths are comparable to those in similar compounds like for example in P(O)[NHC(O)C₆H₄(4-NO₂)][NHC₆H₁₁]₂ (Sabbaghi et al., 2010). As can be expected, the N8—C26 bond length is shorter than the other N—C bonds in the molecule.

The phosphorus atom has a slightly distorted tetrahedral configuration, the bond angles around the P atom are in the range of 103.85 (6)° [N6—P1—N7] to 118.67 (6)° [O2—P1—N7]. The average of surrounding angles around the tertiary nitrogen atom N6 (119.7°) shows that it is bonded in an essentially planar geometry; whereas, the environment of N7 is slightly deviated from planarity (average of bond angles around N7 atom is equal to 117.3°). Furthermore, the angle C26—N8—P1 is 124.98 (10)°.

The oxygen atom of P═O group is a better H-acceptor than that of the C═ O counterpart; so, the hydrogen atom of the C(O)NHP(O) moiety is involving in an intermolecular –P═O···H—N– hydrogen bond (see Table 1) to form a centrosymmetric dimer [graph set: R₂²(8) (Etter et al., 1990; Bernstein et al., 1995)].

Related literature top

For phosphorus compounds with general formula XP(O)[N(CH₃)(CH₂C₆H₅)]₂, see: Gholivand et al. (2005). For bond lengths in a related structure, see: Sabbaghi et al. (2010). For a comparison between the H-acceptor ability of P═O and C═O groups and hydrogen-bond motifs, see: Etter et al. (1990); Bernstein et al. (1995).

Experimental top

4-NO₂—C₆H₄C(O)NHP(O)Cl₂ was prepared according to the procedure of literature (Sabbaghi et al., 2010). To a solution of (2 mmol) 4-NO₂C₆H₄C(O)NHP(O)Cl₂ in CH₃CN (20 ml), a solution of N-methylbenzyl amine (8 mmol) in CH₃CN (5 ml) was added dropwise at 273 K. After 4 h stirring, the solvent was removed in vacuum. Single crystals were obtained from a solution of title compound in C₂H₅OH after slow evaporation at room temperature. IR (KBr, cm^-1): 3141, 2881, 1680, 1604, 1522, 1452, 1342, 1273, 1186, 1104, 1005, 949, 853, 793, 708.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008; software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

Fig. 1. An ORTEP style plot of title compound with the atom-labeling scheme. Ellipsoids are shown at the 50% probability level. H atoms are represented as small spheres of arbitrary radii.

N,N'-Dibenzyl-N,N'-dimethyl-N''- (4-nitrobenzoyl)phosphoric triamide top

Crystal data top

C₂₃H₂₅N₄O₄P	Z = 2
M_r = 452.44	F(000) = 476
Triclinic, P1	D_x = 1.344 Mg m⁻³
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54180 Å
a = 8.3526 (5) Å	Cell parameters from 5608 reflections
b = 11.8150 (5) Å	θ = 3.7–70.5°
c = 12.2668 (4) Å	µ = 1.41 mm⁻¹
α = 77.184 (3)°	T = 297 K
β = 81.289 (4)°	Prismatic, colorless
γ = 71.928 (4)°	0.24 × 0.14 × 0.05 mm
V = 1117.70 (9) Å³

Data collection top

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	4203 independent reflections
Radiation source: Enhance (Cu) X-ray Source	3779 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
Detector resolution: 10.2673 pixels mm^-1	θ_max = 70.6°, θ_min = 3.7°
ω scans	h = −10→10
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −12→14
T_min = 0.941, T_max = 1.000	l = −14→14
8669 measured reflections

Refinement top

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)] = 0.035	All H-atom parameters refined
wR(F²) = 0.093	w = 1/[σ²(F_o²) + (0.049P)² + 0.1381P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
4203 reflections	Δρ_max = 0.21 e Å⁻³
390 parameters	Δρ_min = −0.26 e Å⁻³
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0073 (5)

Crystal data top

C₂₃H₂₅N₄O₄P	γ = 71.928 (4)°
M_r = 452.44	V = 1117.70 (9) Å³
Triclinic, P1	Z = 2
a = 8.3526 (5) Å	Cu Kα radiation
b = 11.8150 (5) Å	µ = 1.41 mm⁻¹
c = 12.2668 (4) Å	T = 297 K
α = 77.184 (3)°	0.24 × 0.14 × 0.05 mm
β = 81.289 (4)°

Data collection top

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	4203 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	3779 reflections with I > 2σ(I)
T_min = 0.941, T_max = 1.000	R_int = 0.025
8669 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.093	All H-atom parameters refined
S = 1.05	Δρ_max = 0.21 e Å⁻³
4203 reflections	Δρ_min = −0.26 e Å⁻³
390 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	0.37947 (4)	0.43216 (3)	0.68154 (3)	0.03514 (12)
O2	0.39241 (13)	0.55008 (8)	0.61457 (8)	0.0441 (2)
O3	0.40102 (16)	0.16957 (10)	0.70306 (10)	0.0570 (3)
O4	1.0449 (2)	−0.09851 (14)	0.30155 (13)	0.0866 (5)
O5	0.9874 (2)	−0.24087 (12)	0.42737 (14)	0.0867 (5)
N6	0.18214 (15)	0.43519 (10)	0.71762 (10)	0.0422 (3)
N7	0.46802 (15)	0.38121 (10)	0.80040 (10)	0.0415 (3)
N8	0.48310 (16)	0.32916 (10)	0.59984 (10)	0.0404 (3)
N9	0.9666 (2)	−0.13399 (13)	0.38622 (13)	0.0594 (4)
C10	−0.08796 (18)	0.59948 (13)	0.70707 (13)	0.0455 (3)
C11	−0.2562 (2)	0.61378 (15)	0.69736 (16)	0.0559 (4)
C12	−0.3838 (2)	0.69259 (18)	0.7548 (2)	0.0693 (6)
C13	−0.3441 (3)	0.75656 (19)	0.82172 (19)	0.0718 (6)
C14	−0.1776 (3)	0.7439 (2)	0.8315 (2)	0.0717 (5)
C15	−0.0499 (2)	0.66649 (16)	0.77376 (17)	0.0587 (4)
C16	0.0512 (2)	0.51473 (15)	0.64516 (14)	0.0494 (4)
C17	0.1226 (2)	0.34870 (15)	0.80655 (16)	0.0537 (4)
C18	0.3946 (3)	0.44794 (17)	0.89219 (14)	0.0563 (4)
C19	0.6514 (2)	0.32321 (15)	0.80428 (14)	0.0484 (3)
C20	0.69385 (18)	0.22357 (14)	0.90560 (12)	0.0451 (3)
C21	0.7774 (2)	0.2365 (2)	0.98905 (15)	0.0615 (4)
C22	0.8215 (3)	0.1426 (3)	1.08008 (17)	0.0796 (6)
C23	0.7830 (3)	0.0367 (2)	1.08917 (18)	0.0742 (6)
C24	0.7001 (3)	0.02349 (18)	1.00715 (18)	0.0697 (5)
C25	0.6558 (3)	0.11582 (16)	0.91598 (16)	0.0592 (4)
C26	0.48804 (18)	0.20940 (12)	0.62439 (11)	0.0402 (3)
C27	0.61200 (18)	0.12548 (12)	0.55456 (11)	0.0392 (3)
C28	0.7086 (2)	0.16247 (13)	0.45913 (12)	0.0478 (4)
C29	0.8241 (2)	0.07733 (14)	0.40268 (13)	0.0526 (4)
C30	0.8402 (2)	−0.04361 (13)	0.44417 (13)	0.0461 (3)
C31	0.7468 (2)	−0.08292 (14)	0.53841 (15)	0.0543 (4)
C32	0.6313 (2)	0.00252 (14)	0.59370 (15)	0.0515 (4)
H11	−0.278 (3)	0.569 (2)	0.6490 (18)	0.069 (6)*
H12	−0.499 (4)	0.701 (2)	0.745 (2)	0.092 (7)*
H13	−0.432 (3)	0.809 (2)	0.860 (2)	0.087 (7)*
H14	−0.154 (3)	0.786 (2)	0.882 (2)	0.093 (8)*
H15	0.067 (3)	0.6575 (19)	0.7821 (18)	0.070 (6)*
H16A	0.104 (2)	0.5613 (17)	0.5845 (17)	0.054 (5)*
H16B	0.001 (3)	0.4617 (19)	0.6165 (17)	0.061 (5)*
H17A	0.041 (3)	0.3951 (19)	0.8615 (18)	0.067 (6)*
H17B	0.218 (3)	0.292 (2)	0.843 (2)	0.076 (6)*
H17C	0.070 (3)	0.303 (2)	0.7758 (19)	0.076 (6)*
H18A	0.276 (3)	0.490 (2)	0.885 (2)	0.084 (7)*
H18B	0.444 (3)	0.512 (3)	0.892 (2)	0.096 (8)*
H18C	0.407 (3)	0.394 (2)	0.964 (2)	0.088 (7)*
H19A	0.702 (3)	0.3836 (19)	0.8089 (17)	0.061 (5)*
H19B	0.693 (2)	0.2926 (17)	0.7372 (17)	0.057 (5)*
H21	0.803 (3)	0.312 (2)	0.9826 (19)	0.074 (6)*
H22	0.878 (4)	0.154 (3)	1.137 (3)	0.117 (10)*
H23	0.810 (3)	−0.029 (3)	1.148 (2)	0.096 (8)*
H24	0.672 (3)	−0.051 (2)	1.009 (2)	0.078 (6)*
H25	0.600 (3)	0.1054 (19)	0.8612 (19)	0.069 (6)*
H28	0.698 (2)	0.2437 (19)	0.4309 (17)	0.061 (5)*
H29	0.894 (3)	0.101 (2)	0.3376 (19)	0.070 (6)*
H31	0.766 (3)	−0.165 (2)	0.5660 (18)	0.069 (6)*
H32	0.565 (3)	−0.0228 (19)	0.6597 (18)	0.066 (6)*
H8	0.533 (2)	0.3600 (17)	0.5403 (17)	0.049 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P1	0.0438 (2)	0.02572 (18)	0.03071 (18)	−0.00681 (13)	0.00261 (13)	−0.00327 (12)
O2	0.0586 (6)	0.0298 (5)	0.0380 (5)	−0.0110 (4)	0.0061 (4)	−0.0035 (4)
O3	0.0742 (7)	0.0362 (5)	0.0535 (6)	−0.0178 (5)	0.0162 (5)	−0.0060 (5)
O4	0.0973 (11)	0.0691 (9)	0.0630 (9)	0.0154 (8)	0.0114 (8)	−0.0189 (7)
O5	0.1171 (13)	0.0377 (7)	0.0854 (10)	0.0103 (7)	−0.0052 (9)	−0.0200 (7)
N6	0.0434 (6)	0.0352 (6)	0.0402 (6)	−0.0065 (5)	0.0002 (5)	−0.0006 (5)
N7	0.0460 (6)	0.0371 (6)	0.0354 (6)	−0.0048 (5)	−0.0009 (5)	−0.0064 (5)
N8	0.0530 (7)	0.0292 (5)	0.0337 (6)	−0.0098 (5)	0.0060 (5)	−0.0044 (4)
N9	0.0701 (9)	0.0463 (8)	0.0522 (8)	0.0072 (6)	−0.0137 (7)	−0.0185 (6)
C10	0.0418 (7)	0.0386 (7)	0.0505 (8)	−0.0079 (6)	−0.0075 (6)	0.0004 (6)
C11	0.0500 (9)	0.0452 (8)	0.0674 (10)	−0.0159 (7)	−0.0141 (8)	0.0087 (8)
C12	0.0398 (9)	0.0600 (11)	0.0866 (14)	−0.0080 (8)	−0.0010 (8)	0.0178 (10)
C13	0.0578 (11)	0.0591 (11)	0.0732 (12)	0.0025 (9)	0.0135 (9)	−0.0011 (10)
C14	0.0686 (12)	0.0629 (11)	0.0768 (13)	−0.0026 (9)	−0.0034 (10)	−0.0243 (10)
C15	0.0469 (9)	0.0555 (10)	0.0723 (11)	−0.0054 (7)	−0.0089 (8)	−0.0198 (8)
C16	0.0514 (8)	0.0469 (8)	0.0468 (8)	−0.0072 (7)	−0.0101 (7)	−0.0086 (7)
C17	0.0516 (9)	0.0425 (8)	0.0578 (10)	−0.0134 (7)	0.0105 (8)	−0.0012 (7)
C18	0.0698 (11)	0.0528 (10)	0.0400 (8)	−0.0051 (8)	−0.0041 (7)	−0.0146 (7)
C19	0.0449 (8)	0.0500 (9)	0.0451 (8)	−0.0141 (7)	−0.0012 (6)	0.0005 (7)
C20	0.0377 (7)	0.0486 (8)	0.0418 (7)	−0.0068 (6)	−0.0007 (5)	−0.0036 (6)
C21	0.0593 (10)	0.0786 (13)	0.0509 (9)	−0.0310 (9)	−0.0070 (7)	−0.0029 (8)
C22	0.0693 (12)	0.1179 (19)	0.0511 (10)	−0.0358 (12)	−0.0214 (9)	0.0091 (11)
C23	0.0635 (11)	0.0782 (14)	0.0599 (11)	−0.0073 (10)	−0.0144 (9)	0.0174 (10)
C24	0.0835 (14)	0.0454 (10)	0.0674 (12)	−0.0087 (9)	−0.0101 (10)	0.0039 (8)
C25	0.0723 (11)	0.0496 (9)	0.0524 (9)	−0.0128 (8)	−0.0143 (8)	−0.0037 (7)
C26	0.0502 (8)	0.0306 (6)	0.0365 (7)	−0.0097 (6)	−0.0020 (6)	−0.0034 (5)
C27	0.0493 (7)	0.0294 (6)	0.0370 (7)	−0.0073 (5)	−0.0076 (6)	−0.0056 (5)
C28	0.0675 (10)	0.0283 (7)	0.0388 (7)	−0.0052 (6)	−0.0007 (7)	−0.0035 (6)
C29	0.0698 (10)	0.0393 (8)	0.0377 (7)	−0.0044 (7)	0.0022 (7)	−0.0058 (6)
C30	0.0548 (8)	0.0353 (7)	0.0434 (8)	0.0017 (6)	−0.0126 (6)	−0.0128 (6)
C31	0.0673 (10)	0.0279 (7)	0.0617 (10)	−0.0059 (7)	−0.0064 (8)	−0.0069 (7)
C32	0.0605 (9)	0.0320 (7)	0.0558 (9)	−0.0105 (6)	0.0018 (7)	−0.0042 (6)

Geometric parameters (Å, º) top

P1—O2	1.4787 (10)	C17—H17C	0.95 (2)
P1—N6	1.6319 (13)	C18—H18A	0.97 (3)
P1—N7	1.6420 (12)	C18—H18B	0.96 (3)
P1—N8	1.6910 (11)	C18—H18C	0.97 (3)
O3—C26	1.2163 (18)	C19—C20	1.510 (2)
O4—N9	1.206 (2)	C19—H19A	0.95 (2)
O5—N9	1.219 (2)	C19—H19B	0.95 (2)
N6—C17	1.462 (2)	C20—C25	1.380 (3)
N6—C16	1.4684 (19)	C20—C21	1.382 (2)
N7—C18	1.4663 (19)	C21—C22	1.391 (3)
N7—C19	1.474 (2)	C21—H21	0.96 (2)
N8—C26	1.3686 (18)	C22—C23	1.364 (4)
N8—H8	0.85 (2)	C22—H22	0.96 (3)
N9—C30	1.4729 (19)	C23—C24	1.365 (3)
C10—C11	1.383 (2)	C23—H23	0.93 (3)
C10—C15	1.385 (2)	C24—C25	1.383 (3)
C10—C16	1.509 (2)	C24—H24	0.97 (2)
C11—C12	1.395 (3)	C25—H25	0.92 (2)
C11—H11	0.95 (2)	C26—C27	1.5035 (19)
C12—C13	1.367 (3)	C27—C28	1.385 (2)
C12—H12	0.96 (3)	C27—C32	1.391 (2)
C13—C14	1.373 (3)	C28—C29	1.388 (2)
C13—H13	0.94 (3)	C28—H28	0.93 (2)
C14—C15	1.389 (3)	C29—C30	1.377 (2)
C14—H14	0.96 (3)	C29—H29	0.96 (2)
C15—H15	0.97 (2)	C30—C31	1.369 (2)
C16—H16A	0.96 (2)	C31—C32	1.383 (2)
C16—H16B	1.00 (2)	C31—H31	0.92 (2)
C17—H17A	1.01 (2)	C32—H32	0.96 (2)
C17—H17B	0.96 (2)

O2—P1—N6	110.89 (6)	H18A—C18—H18B	104 (2)
O2—P1—N7	118.67 (6)	N7—C18—H18C	110.9 (15)
N6—P1—N7	103.85 (6)	H18A—C18—H18C	110 (2)
O2—P1—N8	105.24 (6)	H18B—C18—H18C	108 (2)
N6—P1—N8	113.52 (6)	N7—C19—C20	112.83 (12)
N7—P1—N8	104.82 (6)	N7—C19—H19A	107.8 (12)
C17—N6—C16	113.89 (13)	C20—C19—H19A	107.4 (12)
C17—N6—P1	125.48 (11)	N7—C19—H19B	108.0 (11)
C16—N6—P1	119.62 (10)	C20—C19—H19B	110.6 (12)
C18—N7—C19	112.51 (13)	H19A—C19—H19B	110.2 (17)
C18—N7—P1	117.29 (10)	C25—C20—C21	118.07 (16)
C19—N7—P1	122.11 (10)	C25—C20—C19	121.29 (15)
C26—N8—P1	124.98 (10)	C21—C20—C19	120.60 (16)
C26—N8—H8	122.7 (12)	C20—C21—C22	120.3 (2)
P1—N8—H8	112.4 (12)	C20—C21—H21	118.3 (14)
O4—N9—O5	123.56 (15)	C22—C21—H21	121.4 (14)
O4—N9—C30	118.42 (14)	C23—C22—C21	121.0 (2)
O5—N9—C30	118.01 (16)	C23—C22—H22	120.3 (19)
C11—C10—C15	118.31 (16)	C21—C22—H22	118.7 (19)
C11—C10—C16	121.02 (15)	C22—C23—C24	119.00 (19)
C15—C10—C16	120.65 (14)	C22—C23—H23	124.1 (17)
C10—C11—C12	120.54 (18)	C24—C23—H23	116.9 (17)
C10—C11—H11	116.3 (13)	C23—C24—C25	120.7 (2)
C12—C11—H11	123.1 (13)	C23—C24—H24	121.8 (14)
C13—C12—C11	120.40 (18)	C25—C24—H24	117.5 (14)
C13—C12—H12	121.6 (16)	C20—C25—C24	120.95 (19)
C11—C12—H12	118.0 (16)	C20—C25—H25	119.4 (13)
C12—C13—C14	119.66 (19)	C24—C25—H25	119.6 (14)
C12—C13—H13	119.4 (15)	O3—C26—N8	121.84 (13)
C14—C13—H13	120.9 (16)	O3—C26—C27	120.11 (12)
C13—C14—C15	120.3 (2)	N8—C26—C27	117.97 (12)
C13—C14—H14	117.8 (16)	C28—C27—C32	119.72 (13)
C15—C14—H14	121.8 (17)	C28—C27—C26	124.63 (12)
C10—C15—C14	120.80 (18)	C32—C27—C26	115.62 (13)
C10—C15—H15	119.7 (13)	C27—C28—C29	120.19 (14)
C14—C15—H15	119.5 (13)	C27—C28—H28	121.6 (12)
N6—C16—C10	112.55 (12)	C29—C28—H28	118.2 (12)
N6—C16—H16A	108.2 (11)	C30—C29—C28	118.48 (15)
C10—C16—H16A	109.3 (11)	C30—C29—H29	120.0 (13)
N6—C16—H16B	107.3 (12)	C28—C29—H29	121.5 (13)
C10—C16—H16B	108.7 (12)	C31—C30—C29	122.66 (14)
H16A—C16—H16B	110.8 (16)	C31—C30—N9	118.90 (14)
N6—C17—H17A	108.4 (12)	C29—C30—N9	118.42 (15)
N6—C17—H17B	109.0 (14)	C30—C31—C32	118.49 (14)
H17A—C17—H17B	110.9 (18)	C30—C31—H31	120.1 (13)
N6—C17—H17C	110.5 (14)	C32—C31—H31	121.3 (14)
H17A—C17—H17C	110.8 (18)	C31—C32—C27	120.47 (16)
H17B—C17—H17C	107 (2)	C31—C32—H32	120.0 (13)
N7—C18—H18A	110.9 (15)	C27—C32—H32	119.6 (13)
N7—C18—H18B	113.1 (17)

O2—P1—N6—C17	−162.93 (13)	N7—C19—C20—C21	−112.67 (17)
N7—P1—N6—C17	−34.39 (15)	C25—C20—C21—C22	0.2 (3)
N8—P1—N6—C17	78.85 (14)	C19—C20—C21—C22	−177.67 (17)
O2—P1—N6—C16	29.27 (13)	C20—C21—C22—C23	−0.2 (3)
N7—P1—N6—C16	157.80 (11)	C21—C22—C23—C24	0.1 (3)
N8—P1—N6—C16	−88.96 (12)	C22—C23—C24—C25	0.1 (3)
O2—P1—N7—C18	67.60 (14)	C21—C20—C25—C24	−0.1 (3)
N6—P1—N7—C18	−56.00 (14)	C19—C20—C25—C24	177.82 (17)
N8—P1—N7—C18	−175.36 (13)	C23—C24—C25—C20	−0.1 (3)
O2—P1—N7—C19	−78.73 (13)	P1—N8—C26—O3	8.3 (2)
N6—P1—N7—C19	157.67 (12)	P1—N8—C26—C27	−168.53 (10)
N8—P1—N7—C19	38.30 (13)	O3—C26—C27—C28	175.52 (15)
O2—P1—N8—C26	−173.12 (12)	N8—C26—C27—C28	−7.6 (2)
N6—P1—N8—C26	−51.67 (14)	O3—C26—C27—C32	−6.7 (2)
N7—P1—N8—C26	60.98 (14)	N8—C26—C27—C32	170.15 (14)
C15—C10—C11—C12	−0.9 (2)	C32—C27—C28—C29	0.0 (2)
C16—C10—C11—C12	−179.86 (15)	C26—C27—C28—C29	177.69 (15)
C10—C11—C12—C13	−0.2 (3)	C27—C28—C29—C30	−0.3 (3)
C11—C12—C13—C14	0.6 (3)	C28—C29—C30—C31	0.2 (3)
C12—C13—C14—C15	−0.1 (3)	C28—C29—C30—N9	−178.13 (15)
C11—C10—C15—C14	1.5 (3)	O4—N9—C30—C31	177.97 (17)
C16—C10—C15—C14	−179.55 (18)	O5—N9—C30—C31	−2.8 (2)
C13—C14—C15—C10	−1.0 (3)	O4—N9—C30—C29	−3.7 (2)
C17—N6—C16—C10	65.91 (18)	O5—N9—C30—C29	175.58 (17)
P1—N6—C16—C10	−124.93 (13)	C29—C30—C31—C32	0.2 (3)
C11—C10—C16—N6	−132.44 (15)	N9—C30—C31—C32	178.54 (15)
C15—C10—C16—N6	48.6 (2)	C30—C31—C32—C27	−0.5 (3)
C18—N7—C19—C20	66.18 (18)	C28—C27—C32—C31	0.4 (2)
P1—N7—C19—C20	−146.04 (12)	C26—C27—C32—C31	−177.47 (15)
N7—C19—C20—C25	69.5 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N8—H8···O2ⁱ	0.85 (2)	2.07 (2)	2.909 (2)	169 (2)

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₃H₂₅N₄O₄P
M_r	452.44
Crystal system, space group	Triclinic, P1
Temperature (K)	297
a, b, c (Å)	8.3526 (5), 11.8150 (5), 12.2668 (4)
α, β, γ (°)	77.184 (3), 81.289 (4), 71.928 (4)
V (Å³)	1117.70 (9)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	1.41
Crystal size (mm)	0.24 × 0.14 × 0.05

Data collection
Diffractometer	Oxford Diffraction Xcalibur Ruby Gemini diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)
T_min, T_max	0.941, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	8669, 4203, 3779
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.612

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.093, 1.05
No. of reflections	4203
No. of parameters	390
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.26

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), SIR2004 (Burla et al., 2005), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2008, WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N8—H8···O2ⁱ	0.85 (2)	2.07 (2)	2.909 (2)	169 (2)

Symmetry code: (i) −x+1, −y+1, −z+1.

Acknowledgements

Financial support from the Spanish Ministerio de Educacion y Ciencia (MAT2006–01997, MAT2010–15094 and the `Factoría de Cristalización' Consolider Ingenio 2010) and FEDER funding is acknowledged.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381–388. Web of Science CrossRef CAS IUCr Journals Google Scholar
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256–262. CrossRef CAS Web of Science IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Gholivand, K., Pourayoubi, M., Shariatinia, Z. & Mostaanzadeh, H. (2005). Polyhedron, 24, 655–662. Web of Science CSD CrossRef CAS 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
Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England. Google Scholar
Sabbaghi, F., Pourayoubi, M., Toghraee, M. & Divjakovic, V. (2010). Acta Cryst. E66, o344. 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