Diethyl [(9-anthr­yl)(4-methyl­anilino)meth­yl]phospho­nate

Kraicheva, I.; Tsacheva, I.; Vodenicharova, E.; Tashev, E.; Troev, K.

doi:10.1107/S1600536811025943

organic compounds

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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o1980

doi:10.1107/S1600536811025943

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Diethyl [(9-anthryl)(4-methylanilino)methyl]phosphonate

Ivanka Kraicheva,^a ^* Ivelina Tsacheva,^a Elitsa Vodenicharova,^a Emil Tashev ^a and Kolio Troev ^a

^aInstitute of Polymers, Bulgarian Academy of Sciences, Acad. G. Bonchev str., bl. 103A, 1113 Sofia, Bulgaria
^*Correspondence e-mail: kraicheva@yahoo.com

(Received 13 June 2011; accepted 30 June 2011; online 9 July 2011)

The title compound, C₂₆H₂₈NO₃P, crystallized with two independent molecules in the asymmetric unit. The structural features (bond lengths and angles) of the two molecules are almost identical. The interplanar angle between the anthracene and toluidine rings is similar in the two molecules, with values of 82.92 (5) and 80.70 (5)°. In the crystal, both molecules form inversion dimers linked by pairs of N—H⋯O hydrogen bonds. Three of the four ethyl groups are disordered over two sets of sites, the major components having occupancies of 0.748 (15), 0.77 (4) and 0.518 (19).

Related literature

For general background of the use of aminophosphonic acid derivatives in organic synthesis and as biologically active compounds, see: Kraicheva et al. (2011 ).

Experimental

Crystal data

C₂₆H₂₈NO₃P
M_r = 433.46
Triclinic, $[P \overline 1]$
a = 9.5990 (3) Å
b = 12.6386 (5) Å
c = 20.2131 (7) Å
α = 75.865 (3)°
β = 76.780 (4)°
γ = 74.927 (3)°
V = 2260.13 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.15 mm⁻¹
T = 290 K
0.31 × 0.18 × 0.15 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ) T_min = 0.947, T_max = 1.000
20827 measured reflections
12691 independent reflections
8114 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.056
wR(F²) = 0.153
S = 1.02
12691 reflections
637 parameters
4 restraints
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.98	2.02	2.990 (2)	170
N1B—H1B⋯O21ⁱⁱ	0.90	2.15	3.016 (2)	163
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+1, -y, -z.

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008; molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811025943/ng5182sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811025943/ng5182Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811025943/ng5182Isup3.cml

checkCIF report

Comment top

Aminophosphonic acid derivatives constitute an important class of biologically active compounds with a great potential for medicinal and pharmaceutical applications. They are phosphorus analogues of natural alpha-aminocarboxylic acids - the bilding blocks of peptides and proteins Due to the close structural resemblance, aminophosphonates can mimic the aminoacids and can act as inhibitors and regulators of metabolic processes. Therefore they are extremely useful in the development of potential drugs against several metabolic disorders. Moreover, many of aminophosphonate derivatives exhibit antibacterial, antiviral and anticancer activity. The title compound has been synthesized and tested for cytotoxicity on Balb/c 3 T3 (clone31) cells, for in vitro antitumor activity using a panel of six human epithelial cancer cell lines and for genotoxicity and antiproliferative activity in vivo. Here we report its crystal structure.

The title compound (Fig. 1) possesses three distinct functional groups: anthracen, diethyl phosphonate and p-toluidine. It crystallizes with two independent molecules in the assymetric unit. The anthracen and toluidine moieties are nearly planar (with respective r.m.s. of 0.014/0.003 and 0.017/0.005Å for molecule A and B).

The interplanar angle beteween the anthracen and the toluidine is 82.92 (5) and 80.70 (5) °.

One can say that the diethyl phosphonate moiety is also positioned in the toluidine mean plane thus inferring a T-shape to the molecule.

In the crystal structure of the studied compound symmetrically equivalent molecules are linked together by N—H···O hydrogen bonds to form cyclic dimmers (Fig. 2).

Three of the four ethyl moieties present in the crystal structure of the title compound are disordered over two positions. The positional disorder on the O and C ethyl atoms was resolved by finding alternative positions from the difference Fourier map, and was subsequently refined over two positions. Where necessary bonds were constrained to distances of 1.54 (5) Å (P—O) and 1. 44 (5) Å (O—C and C—C). The occupancies of the component of the ethyl fragments starting with O2, O3 and O22 atoms are 0.737 (5), 0.755 (2) and 0.482 (3) respectively.

Related literature top

For general background of the use of aminophosphonic acid derivatives in organic synthesis and as biologically active compounds, see: Kraicheva et al. (2011).

Experimental top

The studied compound has been obtained according to Kraicheva et al. 2011. Suitable crystals were obtained by slow evaporation from methanol/methylen chloride solution (1:1 v/v) at room temperature.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008; molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The asymmetric unit of title compound with the atom numbering scheme showing 50% probability displacement ellipsoids. H atoms have been omitted for clarity. The minor disorder component is shown as dasshed lines.
	Fig. 2. The packing arrangement of the molecules in the unit cell, showing the hydrogen-bonding interactions as dashed lines. [symmetry codes: (i) 1 - x, 1 - y, 1 - z; (ii) 1 - x, 1 - y, -z]

Diethyl [(9-anthryl)(4-methylanilino)methyl]phosphonate top

Crystal data top

C₂₆H₂₈NO₃P	F(000) = 920
M_r = 433.46	D_x = 1.274 Mg m⁻³
Triclinic, P1	Melting point = 406–407 K
a = 9.5990 (3) Å	Mo Kα radiation, λ = 0.7107 Å
b = 12.6386 (5) Å	Cell parameters from 6846 reflections
c = 20.2131 (7) Å	θ = 2.8–31.3°
α = 75.865 (3)°	µ = 0.15 mm⁻¹
β = 76.780 (4)°	T = 290 K
γ = 74.927 (3)°	Prism, yellow
V = 2260.13 (14) Å³	0.31 × 0.18 × 0.15 mm
Z = 4

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	12691 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	8114 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.036
Detector resolution: 10.3974 pixels mm^-1	θ_max = 30.0°, θ_min = 2.8°
ω scans	h = −12→13
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −17→13
T_min = 0.947, T_max = 1.000	l = −28→28
20827 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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.153	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0574P)² + 0.3871P] where P = (F_o² + 2F_c²)/3
12691 reflections	(Δ/σ)_max = 0.001
637 parameters	Δρ_max = 0.29 e Å⁻³
4 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

C₂₆H₂₈NO₃P	γ = 74.927 (3)°
M_r = 433.46	V = 2260.13 (14) Å³
Triclinic, P1	Z = 4
a = 9.5990 (3) Å	Mo Kα radiation
b = 12.6386 (5) Å	µ = 0.15 mm⁻¹
c = 20.2131 (7) Å	T = 290 K
α = 75.865 (3)°	0.31 × 0.18 × 0.15 mm
β = 76.780 (4)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	12691 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	8114 reflections with I > 2σ(I)
T_min = 0.947, T_max = 1.000	R_int = 0.036
20827 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	4 restraints
wR(F²) = 0.153	H-atom parameters constrained
S = 1.02	Δρ_max = 0.29 e Å⁻³
12691 reflections	Δρ_min = −0.34 e Å⁻³
637 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	Occ. (<1)
C101	0.32852 (19)	0.42066 (15)	0.42195 (9)	0.0383 (4)
H101	0.2516	0.3873	0.4545	0.046*
C102	0.32061 (18)	0.40400 (14)	0.35010 (9)	0.0360 (4)
C103	0.38352 (19)	0.46855 (15)	0.28834 (9)	0.0399 (4)
C104	0.4604 (2)	0.55260 (17)	0.28607 (11)	0.0502 (5)
H104	0.4707	0.5669	0.3275	0.060*
C105	0.5185 (3)	0.6119 (2)	0.22562 (12)	0.0632 (6)
H105	0.5685	0.6654	0.2264	0.076*
C106	0.5050 (3)	0.5943 (2)	0.16170 (12)	0.0741 (7)
H106	0.5444	0.6367	0.1206	0.089*
C107	0.4352 (3)	0.5163 (2)	0.16009 (11)	0.0675 (7)
H107	0.4271	0.5048	0.1175	0.081*
C108	0.3723 (2)	0.45006 (18)	0.22268 (9)	0.0470 (5)
C109	0.3007 (2)	0.36943 (19)	0.22033 (10)	0.0523 (5)
H109	0.2944	0.3582	0.1774	0.063*
C110	0.2384 (2)	0.30518 (16)	0.27977 (10)	0.0440 (4)
C111	0.1637 (3)	0.22403 (19)	0.27558 (12)	0.0587 (6)
H111	0.1601	0.2128	0.2323	0.070*
C113	0.1044 (3)	0.17947 (19)	0.39868 (13)	0.0623 (6)
H113	0.0585	0.1377	0.4382	0.075*
C114	0.1760 (2)	0.25470 (17)	0.40555 (10)	0.0502 (5)
H114	0.1789	0.2625	0.4497	0.060*
C115	0.24696 (19)	0.32237 (15)	0.34655 (9)	0.0386 (4)
C116	0.0284 (3)	0.79981 (17)	0.40743 (11)	0.0584 (6)
H116	0.0247	0.8750	0.4046	0.070*
C117	0.1572 (2)	0.72306 (17)	0.41614 (10)	0.0515 (5)
H117	0.2389	0.7475	0.4187	0.062*
C118	0.1675 (2)	0.60930 (15)	0.42123 (8)	0.0402 (4)
C120	0.0428 (2)	0.57649 (16)	0.41685 (9)	0.0443 (4)
H120	0.0457	0.5014	0.4198	0.053*
C121	−0.0860 (2)	0.65542 (18)	0.40804 (10)	0.0493 (5)
H121	−0.1683	0.6316	0.4056	0.059*
C122	−0.0961 (2)	0.76765 (18)	0.40273 (10)	0.0534 (5)
C123	−0.2378 (3)	0.8513 (2)	0.39294 (14)	0.0830 (8)
H23A	−0.2910	0.8245	0.3680	0.124*
H23B	−0.2167	0.9216	0.3672	0.124*
H23C	−0.2958	0.8608	0.4374	0.124*
C126	0.8357 (3)	0.4455 (2)	0.32847 (12)	0.0691 (7)
H26A	0.9106	0.4784	0.3343	0.104*
H26B	0.7788	0.4970	0.2961	0.104*
H26C	0.8804	0.3779	0.3112	0.104*
C201	0.19612 (18)	0.10024 (15)	0.06409 (8)	0.0368 (4)
H201	0.1381	0.0438	0.0711	0.044*
C202	0.09303 (18)	0.19745 (14)	0.09577 (8)	0.0350 (4)
C203	−0.02950 (19)	0.17438 (15)	0.14672 (8)	0.0381 (4)
C204	−0.0612 (2)	0.06593 (18)	0.17192 (10)	0.0501 (5)
H204	0.0024	0.0055	0.1549	0.060*
C205	−0.1815 (3)	0.0481 (2)	0.22005 (11)	0.0650 (6)
H205	−0.1992	−0.0236	0.2348	0.078*
C206	−0.2798 (3)	0.1369 (3)	0.24797 (12)	0.0695 (7)
H206	−0.3616	0.1234	0.2810	0.083*
C207	−0.2557 (2)	0.2408 (2)	0.22694 (11)	0.0616 (6)
H207	−0.3208	0.2987	0.2460	0.074*
C208	−0.1315 (2)	0.26435 (17)	0.17570 (9)	0.0438 (4)
C209	−0.1076 (2)	0.37117 (17)	0.15378 (10)	0.0501 (5)
H209	−0.1754	0.4290	0.1719	0.060*
C210	0.0136 (2)	0.39572 (15)	0.10583 (9)	0.0438 (4)
C211	0.0369 (3)	0.50719 (17)	0.08596 (12)	0.0588 (6)
H211	−0.0311	0.5636	0.1053	0.071*
C212	0.1541 (3)	0.53224 (19)	0.04032 (13)	0.0661 (6)
H212	0.1671	0.6053	0.0280	0.079*
C213	0.2572 (3)	0.44751 (18)	0.01113 (11)	0.0601 (6)
H213	0.3391	0.4653	−0.0202	0.072*
C214	0.2408 (2)	0.34046 (17)	0.02739 (10)	0.0481 (4)
H214	0.3113	0.2867	0.0066	0.058*
C215	0.11737 (19)	0.30786 (14)	0.07585 (9)	0.0374 (4)
C216	−0.0702 (2)	0.19826 (17)	−0.09719 (10)	0.0476 (5)
H216	−0.1698	0.1986	−0.0865	0.057*
C217	0.0126 (2)	0.15950 (16)	−0.04435 (9)	0.0438 (4)
H217	−0.0318	0.1344	0.0008	0.053*
C218	0.16218 (19)	0.15833 (14)	−0.05918 (9)	0.0387 (4)
C220	0.2244 (2)	0.19460 (16)	−0.12763 (10)	0.0454 (4)
H220	0.3244	0.1931	−0.1389	0.055*
C221	0.1408 (2)	0.23251 (17)	−0.17861 (10)	0.0517 (5)
H221	0.1855	0.2565	−0.2238	0.062*
C222	−0.0089 (2)	0.23628 (17)	−0.16500 (10)	0.0476 (5)
C223	−0.0985 (3)	0.2816 (3)	−0.22198 (12)	0.0806 (8)
H23D	−0.1994	0.2799	−0.2031	0.121*
H23E	−0.0632	0.2365	−0.2568	0.121*
H23F	−0.0901	0.3572	−0.2423	0.121*
C226	0.3190 (3)	−0.0812 (2)	0.23724 (13)	0.0782 (7)
H26D	0.3547	−0.1457	0.2153	0.094*
H26E	0.2307	−0.0921	0.2703	0.094*
C227	0.4284 (4)	−0.0743 (3)	0.27378 (16)	0.1135 (12)
H27D	0.5182	−0.0687	0.2418	0.170*
H27E	0.4449	−0.1402	0.3091	0.170*
H27F	0.3946	−0.0096	0.2947	0.170*
C112	0.0984 (3)	0.1634 (2)	0.33272 (14)	0.0661 (6)
H112	0.0495	0.1112	0.3289	0.079*
N1	0.29837 (18)	0.53514 (13)	0.43061 (8)	0.0485 (4)
H1	0.3674	0.5597	0.4493	0.058*
N1B	0.25112 (17)	0.12429 (14)	−0.00954 (7)	0.0459 (4)
H1B	0.3479	0.1026	−0.0232	0.055*
O1	0.50897 (16)	0.36126 (12)	0.51906 (7)	0.0542 (4)
O2	0.4889 (7)	0.2224 (6)	0.4522 (4)	0.0535 (11)	0.748 (15)
C124	0.6130 (7)	0.1334 (4)	0.4410 (5)	0.0776 (17)	0.748 (15)
H24A	0.6826	0.1609	0.4017	0.093*	0.748 (15)
H24B	0.5814	0.0746	0.4291	0.093*	0.748 (15)
C125	0.6876 (13)	0.0857 (6)	0.5009 (6)	0.128 (4)	0.748 (15)
H25A	0.7685	0.0259	0.4899	0.193*	0.748 (15)
H25B	0.6199	0.0575	0.5400	0.193*	0.748 (15)
H25C	0.7231	0.1425	0.5119	0.193*	0.748 (15)
O2B	0.531 (3)	0.229 (2)	0.4318 (13)	0.078 (6)	0.252 (15)
C324	0.592 (2)	0.1266 (13)	0.4840 (15)	0.094 (6)	0.252 (15)
H32A	0.5727	0.1416	0.5304	0.113*	0.252 (15)
H32B	0.5553	0.0617	0.4847	0.113*	0.252 (15)
C325	0.742 (2)	0.1148 (19)	0.4540 (14)	0.110 (7)	0.252 (15)
H32C	0.7990	0.0533	0.4817	0.164*	0.252 (15)
H32D	0.7730	0.1822	0.4517	0.164*	0.252 (15)
H32E	0.7567	0.1007	0.4080	0.164*	0.252 (15)
O23	0.28356 (18)	0.01628 (13)	0.18572 (7)	0.0675 (5)
O3	0.6276 (8)	0.3689 (6)	0.3922 (3)	0.0490 (12)	0.77 (4)
C127	0.7412 (11)	0.4202 (8)	0.3947 (6)	0.077 (3)	0.77 (4)
H12D	0.6972	0.4889	0.4118	0.092*	0.77 (4)
H12E	0.8006	0.3710	0.4276	0.092*	0.77 (4)
O3B	0.619 (3)	0.404 (5)	0.3910 (13)	0.079 (7)	0.23 (4)
C273	0.754 (3)	0.4200 (16)	0.4067 (15)	0.046 (4)	0.23 (4)
H27A	0.8060	0.3530	0.4336	0.055*	0.23 (4)
H27B	0.7363	0.4825	0.4296	0.055*	0.23 (4)
O21	0.43711 (15)	−0.07165 (12)	0.08495 (7)	0.0539 (4)
O22	0.4284 (11)	0.1262 (8)	0.1064 (5)	0.0494 (15)	0.482 (19)
C224	0.5885 (18)	0.1236 (15)	0.0752 (7)	0.065 (3)	0.482 (19)
H22D	0.6493	0.0666	0.1045	0.078*	0.482 (19)
H22E	0.6092	0.1035	0.0300	0.078*	0.482 (19)
C225	0.6267 (16)	0.2323 (10)	0.0677 (6)	0.056 (3)	0.482 (19)
H22A	0.7314	0.2229	0.0582	0.084*	0.482 (19)
H22B	0.5877	0.2600	0.1099	0.084*	0.482 (19)
H22C	0.5859	0.2845	0.0302	0.084*	0.482 (19)
O22B	0.4432 (11)	0.1264 (8)	0.0802 (6)	0.0587 (18)	0.518 (19)
C229	0.5762 (16)	0.1197 (14)	0.1033 (8)	0.070 (3)	0.518 (19)
H22F	0.6512	0.0561	0.0911	0.085*	0.518 (19)
H22G	0.5600	0.1150	0.1530	0.085*	0.518 (19)
C425	0.616 (2)	0.2254 (15)	0.0652 (9)	0.112 (6)	0.518 (19)
H42A	0.6900	0.2392	0.0847	0.168*	0.518 (19)
H42B	0.5306	0.2852	0.0685	0.168*	0.518 (19)
H42C	0.6523	0.2210	0.0174	0.168*	0.518 (19)
P1	0.49980 (6)	0.34524 (4)	0.45120 (3)	0.04332 (14)
P1B	0.35236 (5)	0.03141 (4)	0.10715 (3)	0.04175 (13)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C101	0.0405 (9)	0.0401 (9)	0.0382 (9)	−0.0057 (8)	−0.0127 (8)	−0.0131 (8)
C102	0.0363 (9)	0.0367 (9)	0.0370 (9)	−0.0004 (7)	−0.0135 (7)	−0.0123 (7)
C103	0.0360 (9)	0.0423 (10)	0.0399 (9)	0.0004 (8)	−0.0097 (7)	−0.0117 (8)
C104	0.0481 (11)	0.0518 (12)	0.0512 (11)	−0.0111 (9)	−0.0118 (9)	−0.0077 (9)
C105	0.0557 (13)	0.0623 (14)	0.0660 (14)	−0.0174 (11)	−0.0052 (11)	−0.0022 (12)
C106	0.0728 (16)	0.0869 (19)	0.0522 (13)	−0.0262 (15)	0.0079 (12)	−0.0026 (13)
C107	0.0696 (15)	0.0884 (18)	0.0393 (11)	−0.0176 (14)	0.0011 (10)	−0.0125 (11)
C108	0.0440 (10)	0.0573 (12)	0.0369 (9)	−0.0030 (9)	−0.0062 (8)	−0.0131 (9)
C109	0.0521 (11)	0.0684 (14)	0.0391 (10)	−0.0034 (10)	−0.0090 (9)	−0.0250 (10)
C110	0.0419 (10)	0.0476 (11)	0.0473 (10)	0.0007 (8)	−0.0145 (8)	−0.0233 (9)
C111	0.0644 (14)	0.0589 (13)	0.0661 (14)	−0.0070 (11)	−0.0234 (12)	−0.0328 (12)
C113	0.0703 (15)	0.0520 (13)	0.0707 (14)	−0.0226 (11)	−0.0216 (12)	−0.0047 (11)
C114	0.0591 (12)	0.0472 (11)	0.0494 (11)	−0.0145 (10)	−0.0174 (10)	−0.0085 (9)
C115	0.0399 (9)	0.0378 (9)	0.0407 (9)	−0.0023 (7)	−0.0141 (8)	−0.0125 (8)
C116	0.0786 (16)	0.0376 (11)	0.0523 (12)	−0.0035 (11)	−0.0083 (11)	−0.0094 (9)
C117	0.0605 (13)	0.0469 (11)	0.0505 (11)	−0.0125 (10)	−0.0100 (10)	−0.0149 (9)
C118	0.0478 (10)	0.0427 (10)	0.0307 (8)	−0.0055 (8)	−0.0086 (8)	−0.0116 (7)
C120	0.0503 (11)	0.0415 (10)	0.0420 (9)	−0.0068 (8)	−0.0102 (8)	−0.0114 (8)
C121	0.0454 (11)	0.0572 (12)	0.0421 (10)	−0.0039 (9)	−0.0081 (9)	−0.0113 (9)
C122	0.0591 (13)	0.0509 (12)	0.0381 (10)	0.0055 (10)	−0.0060 (9)	−0.0070 (9)
C123	0.0782 (18)	0.0672 (16)	0.0792 (17)	0.0191 (14)	−0.0132 (14)	−0.0074 (13)
C126	0.0499 (13)	0.0983 (19)	0.0649 (14)	−0.0136 (13)	−0.0065 (11)	−0.0329 (14)
C201	0.0352 (8)	0.0374 (9)	0.0378 (9)	−0.0014 (7)	−0.0071 (7)	−0.0136 (7)
C202	0.0344 (8)	0.0366 (9)	0.0337 (8)	0.0003 (7)	−0.0105 (7)	−0.0107 (7)
C203	0.0379 (9)	0.0449 (10)	0.0325 (8)	−0.0054 (8)	−0.0085 (7)	−0.0115 (7)
C204	0.0535 (12)	0.0527 (12)	0.0440 (10)	−0.0131 (10)	−0.0016 (9)	−0.0138 (9)
C205	0.0701 (15)	0.0769 (16)	0.0514 (12)	−0.0353 (13)	0.0045 (11)	−0.0123 (12)
C206	0.0564 (14)	0.104 (2)	0.0535 (13)	−0.0337 (14)	0.0101 (11)	−0.0255 (13)
C207	0.0449 (11)	0.0882 (18)	0.0534 (12)	−0.0068 (12)	0.0011 (10)	−0.0340 (12)
C208	0.0363 (9)	0.0571 (12)	0.0389 (9)	−0.0010 (8)	−0.0075 (8)	−0.0198 (9)
C209	0.0481 (11)	0.0520 (12)	0.0499 (11)	0.0082 (9)	−0.0126 (9)	−0.0261 (10)
C210	0.0502 (11)	0.0392 (10)	0.0421 (9)	0.0027 (8)	−0.0155 (9)	−0.0145 (8)
C211	0.0740 (15)	0.0388 (11)	0.0640 (13)	0.0027 (10)	−0.0198 (12)	−0.0198 (10)
C212	0.0927 (19)	0.0393 (11)	0.0672 (14)	−0.0149 (12)	−0.0171 (14)	−0.0086 (11)
C213	0.0709 (15)	0.0497 (12)	0.0576 (13)	−0.0204 (11)	−0.0046 (11)	−0.0053 (10)
C214	0.0509 (11)	0.0434 (11)	0.0479 (10)	−0.0080 (9)	−0.0058 (9)	−0.0100 (9)
C215	0.0400 (9)	0.0353 (9)	0.0370 (9)	−0.0011 (7)	−0.0114 (7)	−0.0106 (7)
C216	0.0389 (10)	0.0560 (12)	0.0498 (11)	−0.0021 (9)	−0.0097 (9)	−0.0209 (9)
C217	0.0428 (10)	0.0495 (11)	0.0380 (9)	−0.0053 (8)	−0.0042 (8)	−0.0146 (8)
C218	0.0395 (9)	0.0357 (9)	0.0416 (9)	0.0005 (7)	−0.0099 (8)	−0.0157 (8)
C220	0.0413 (10)	0.0465 (11)	0.0457 (10)	−0.0070 (8)	−0.0034 (8)	−0.0106 (9)
C221	0.0546 (12)	0.0531 (12)	0.0421 (10)	−0.0073 (10)	−0.0068 (9)	−0.0060 (9)
C222	0.0505 (11)	0.0495 (11)	0.0442 (10)	0.0002 (9)	−0.0160 (9)	−0.0162 (9)
C223	0.0679 (16)	0.111 (2)	0.0574 (14)	0.0031 (15)	−0.0263 (13)	−0.0154 (14)
C226	0.0806 (18)	0.0803 (18)	0.0590 (14)	−0.0117 (15)	−0.0067 (13)	0.0021 (13)
C227	0.109 (3)	0.142 (3)	0.084 (2)	0.012 (2)	−0.055 (2)	−0.016 (2)
C112	0.0738 (16)	0.0536 (13)	0.0876 (17)	−0.0201 (12)	−0.0275 (14)	−0.0258 (13)
N1	0.0481 (9)	0.0455 (9)	0.0609 (10)	−0.0010 (7)	−0.0225 (8)	−0.0251 (8)
N1B	0.0336 (8)	0.0616 (10)	0.0390 (8)	0.0027 (7)	−0.0053 (6)	−0.0184 (7)
O1	0.0599 (9)	0.0638 (9)	0.0471 (8)	−0.0125 (7)	−0.0248 (7)	−0.0124 (7)
O2	0.058 (2)	0.0393 (16)	0.067 (2)	−0.0059 (19)	−0.0242 (17)	−0.0098 (18)
C124	0.087 (3)	0.049 (2)	0.096 (4)	0.007 (2)	−0.021 (3)	−0.032 (3)
C125	0.157 (8)	0.067 (3)	0.177 (8)	0.031 (4)	−0.121 (7)	−0.027 (4)
O2B	0.085 (13)	0.058 (9)	0.104 (14)	0.029 (8)	−0.062 (10)	−0.045 (9)
C324	0.127 (14)	0.052 (8)	0.106 (15)	−0.030 (9)	0.008 (13)	−0.033 (10)
C325	0.100 (14)	0.095 (12)	0.133 (17)	−0.013 (9)	−0.047 (13)	−0.004 (12)
O23	0.0779 (11)	0.0682 (10)	0.0406 (8)	0.0215 (8)	−0.0197 (7)	−0.0129 (7)
O3	0.0478 (18)	0.057 (2)	0.048 (2)	−0.0098 (16)	−0.0123 (15)	−0.0194 (19)
C127	0.072 (4)	0.134 (6)	0.051 (3)	−0.054 (4)	−0.012 (3)	−0.032 (3)
O3B	0.039 (6)	0.11 (2)	0.073 (8)	−0.017 (10)	−0.027 (6)	0.017 (9)
C273	0.039 (6)	0.044 (9)	0.064 (11)	−0.006 (6)	−0.028 (7)	−0.014 (6)
O21	0.0446 (7)	0.0513 (8)	0.0595 (8)	0.0090 (6)	−0.0094 (7)	−0.0197 (7)
O22	0.045 (2)	0.046 (2)	0.058 (4)	−0.0084 (16)	−0.006 (3)	−0.016 (3)
C224	0.050 (4)	0.066 (5)	0.077 (6)	−0.007 (3)	−0.007 (5)	−0.023 (6)
C225	0.048 (5)	0.061 (5)	0.066 (6)	−0.018 (4)	−0.008 (4)	−0.021 (4)
O22B	0.046 (3)	0.062 (3)	0.072 (4)	−0.016 (2)	−0.025 (4)	−0.001 (4)
C229	0.053 (6)	0.070 (4)	0.101 (8)	−0.014 (4)	−0.042 (7)	−0.016 (7)
C425	0.067 (6)	0.156 (12)	0.124 (10)	−0.067 (7)	−0.022 (6)	0.004 (9)
P1	0.0467 (3)	0.0427 (3)	0.0453 (3)	−0.0046 (2)	−0.0201 (2)	−0.0117 (2)
P1B	0.0369 (2)	0.0411 (3)	0.0455 (3)	0.0009 (2)	−0.0121 (2)	−0.0107 (2)

Geometric parameters (Å, º) top

C101—N1	1.446 (2)	C213—C214	1.354 (3)
C101—C102	1.539 (2)	C213—H213	0.9300
C101—P1	1.8208 (17)	C214—C215	1.435 (3)
C101—H101	0.9800	C214—H214	0.9300
C102—C103	1.415 (2)	C216—C222	1.383 (3)
C102—C115	1.417 (2)	C216—C217	1.394 (3)
C103—C104	1.429 (3)	C216—H216	0.9300
C103—C108	1.434 (2)	C217—C218	1.395 (3)
C104—C105	1.351 (3)	C217—H217	0.9300
C104—H104	0.9300	C218—N1B	1.382 (2)
C105—C106	1.403 (3)	C218—C220	1.391 (2)
C105—H105	0.9300	C220—C221	1.369 (3)
C106—C107	1.338 (3)	C220—H220	0.9300
C106—H106	0.9300	C221—C222	1.390 (3)
C107—C108	1.436 (3)	C221—H221	0.9300
C107—H107	0.9300	C222—C223	1.506 (3)
C108—C109	1.384 (3)	C223—H23D	0.9600
C109—C110	1.381 (3)	C223—H23E	0.9600
C109—H109	0.9300	C223—H23F	0.9600
C110—C111	1.423 (3)	C226—O23	1.426 (3)
C110—C115	1.442 (2)	C226—C227	1.446 (4)
C111—C112	1.342 (3)	C226—H26D	0.9700
C111—H111	0.9300	C226—H26E	0.9700
C113—C114	1.357 (3)	C227—H27D	0.9600
C113—C112	1.413 (3)	C227—H27E	0.9600
C113—H113	0.9300	C227—H27F	0.9600
C114—C115	1.432 (3)	C112—H112	0.9300
C114—H114	0.9300	N1—H1	0.9784
C116—C117	1.376 (3)	N1B—H1B	0.8955
C116—C122	1.387 (3)	O1—P1	1.4596 (13)
C116—H116	0.9300	O2—C124	1.428 (9)
C117—C118	1.395 (3)	O2—P1	1.577 (8)
C117—H117	0.9300	C124—C125	1.468 (12)
C118—N1	1.379 (2)	C124—H24A	0.9700
C118—C120	1.392 (3)	C124—H24B	0.9700
C120—C121	1.389 (3)	C125—H25A	0.9600
C120—H120	0.9300	C125—H25B	0.9600
C121—C122	1.376 (3)	C125—H25C	0.9600
C121—H121	0.9300	O2B—P1	1.55 (2)
C122—C123	1.510 (3)	O2B—C324	1.54 (3)
C123—H23A	0.9600	C324—C325	1.41 (3)
C123—H23B	0.9600	C324—H32A	0.9700
C123—H23C	0.9600	C324—H32B	0.9700
C126—C127	1.451 (10)	C325—H32C	0.9600
C126—C273	1.59 (3)	C325—H32D	0.9600
C126—H26A	0.9600	C325—H32E	0.9600
C126—H26B	0.9600	O23—P1B	1.5598 (15)
C126—H26C	0.9600	O3—C127	1.420 (11)
C201—N1B	1.445 (2)	O3—P1	1.537 (7)
C201—C202	1.537 (2)	C127—H12D	0.9700
C201—P1B	1.8200 (17)	C127—H12E	0.9700
C201—H201	0.9800	O3B—C273	1.48 (3)
C202—C203	1.417 (2)	O3B—P1	1.64 (3)
C202—C215	1.420 (2)	C273—H27A	0.9700
C203—C204	1.427 (3)	C273—H27B	0.9700
C203—C208	1.442 (2)	O21—P1B	1.4584 (14)
C204—C205	1.358 (3)	O22—C224	1.517 (18)
C204—H204	0.9300	O22—P1B	1.553 (9)
C205—C206	1.408 (3)	C224—C225	1.48 (2)
C205—H205	0.9300	C224—H22D	0.9700
C206—C207	1.342 (3)	C224—H22E	0.9700
C206—H206	0.9300	C225—H22A	0.9600
C207—C208	1.432 (3)	C225—H22B	0.9600
C207—H207	0.9300	C225—H22C	0.9600
C208—C209	1.376 (3)	O22B—C229	1.432 (16)
C209—C210	1.383 (3)	O22B—P1B	1.583 (9)
C209—H209	0.9300	C229—C425	1.47 (2)
C210—C211	1.429 (3)	C229—H22F	0.9700
C210—C215	1.439 (2)	C229—H22G	0.9700
C211—C212	1.336 (3)	C425—H42A	0.9600
C211—H211	0.9300	C425—H42B	0.9600
C212—C213	1.402 (3)	C425—H42C	0.9600
C212—H212	0.9300

N1—C101—C102	116.10 (14)	C216—C217—H217	120.0
N1—C101—P1	109.21 (11)	C218—C217—H217	120.0
C102—C101—P1	113.18 (12)	N1B—C218—C220	118.43 (17)
N1—C101—H101	105.8	N1B—C218—C217	123.58 (17)
C102—C101—H101	105.8	C220—C218—C217	117.99 (17)
P1—C101—H101	105.8	C221—C220—C218	120.97 (18)
C103—C102—C115	119.87 (15)	C221—C220—H220	119.5
C103—C102—C101	121.64 (15)	C218—C220—H220	119.5
C115—C102—C101	118.49 (15)	C220—C221—C222	122.15 (19)
C102—C103—C104	124.40 (16)	C220—C221—H221	118.9
C102—C103—C108	119.39 (17)	C222—C221—H221	118.9
C104—C103—C108	116.21 (17)	C216—C222—C221	116.85 (17)
C105—C104—C103	122.1 (2)	C216—C222—C223	122.4 (2)
C105—C104—H104	119.0	C221—C222—C223	120.77 (19)
C103—C104—H104	119.0	C222—C223—H23D	109.5
C104—C105—C106	121.2 (2)	C222—C223—H23E	109.5
C104—C105—H105	119.4	H23D—C223—H23E	109.5
C106—C105—H105	119.4	C222—C223—H23F	109.5
C107—C106—C105	119.8 (2)	H23D—C223—H23F	109.5
C107—C106—H106	120.1	H23E—C223—H23F	109.5
C105—C106—H106	120.1	O23—C226—C227	112.8 (3)
C106—C107—C108	121.4 (2)	O23—C226—H26D	109.0
C106—C107—H107	119.3	C227—C226—H26D	109.0
C108—C107—H107	119.3	O23—C226—H26E	109.0
C109—C108—C103	119.85 (18)	C227—C226—H26E	109.0
C109—C108—C107	120.88 (18)	H26D—C226—H26E	107.8
C103—C108—C107	119.3 (2)	C226—C227—H27D	109.5
C110—C109—C108	121.99 (17)	C226—C227—H27E	109.5
C110—C109—H109	119.0	H27D—C227—H27E	109.5
C108—C109—H109	119.0	C226—C227—H27F	109.5
C109—C110—C111	120.60 (18)	H27D—C227—H27F	109.5
C109—C110—C115	119.46 (17)	H27E—C227—H27F	109.5
C111—C110—C115	119.92 (19)	C111—C112—C113	119.6 (2)
C112—C111—C110	121.45 (19)	C111—C112—H112	120.2
C112—C111—H111	119.3	C113—C112—H112	120.2
C110—C111—H111	119.3	C118—N1—C101	122.73 (15)
C114—C113—C112	121.3 (2)	C118—N1—H1	117.3
C114—C113—H113	119.4	C101—N1—H1	119.6
C112—C113—H113	119.4	C218—N1B—C201	123.52 (15)
C113—C114—C115	121.76 (19)	C218—N1B—H1B	118.4
C113—C114—H114	119.1	C201—N1B—H1B	116.9
C115—C114—H114	119.1	C124—O2—P1	123.9 (5)
C102—C115—C114	124.57 (16)	O2—C124—C125	114.0 (9)
C102—C115—C110	119.44 (17)	O2—C124—H24A	108.7
C114—C115—C110	115.99 (17)	C125—C124—H24A	108.7
C117—C116—C122	121.6 (2)	O2—C124—H24B	108.7
C117—C116—H116	119.2	C125—C124—H24B	108.7
C122—C116—H116	119.2	H24A—C124—H24B	107.6
C116—C117—C118	121.2 (2)	C124—C125—H25A	109.5
C116—C117—H117	119.4	C124—C125—H25B	109.5
C118—C117—H117	119.4	H25A—C125—H25B	109.5
N1—C118—C120	123.23 (17)	C124—C125—H25C	109.5
N1—C118—C117	119.26 (17)	H25A—C125—H25C	109.5
C120—C118—C117	117.51 (18)	H25B—C125—H25C	109.5
C121—C120—C118	120.30 (18)	P1—O2B—C324	117.5 (18)
C121—C120—H120	119.8	C325—C324—O2B	98 (3)
C118—C120—H120	119.8	C325—C324—H32A	112.1
C122—C121—C120	122.2 (2)	O2B—C324—H32A	112.1
C122—C121—H121	118.9	C325—C324—H32B	112.1
C120—C121—H121	118.9	O2B—C324—H32B	112.1
C121—C122—C116	117.21 (19)	H32A—C324—H32B	109.7
C121—C122—C123	120.8 (2)	C324—C325—H32C	109.5
C116—C122—C123	122.0 (2)	C324—C325—H32D	109.5
C122—C123—H23A	109.5	H32C—C325—H32D	109.5
C122—C123—H23B	109.5	C324—C325—H32E	109.5
H23A—C123—H23B	109.5	H32C—C325—H32E	109.5
C122—C123—H23C	109.5	H32D—C325—H32E	109.5
H23A—C123—H23C	109.5	C226—O23—P1B	125.73 (15)
H23B—C123—H23C	109.5	C127—O3—P1	126.4 (6)
C127—C126—H26A	109.5	C126—C127—O3	114.1 (8)
C273—C126—H26A	100.0	C126—C127—H12D	108.7
C127—C126—H26B	109.5	O3—C127—H12D	108.7
C273—C126—H26B	116.5	C126—C127—H12E	108.7
H26A—C126—H26B	109.5	O3—C127—H12E	108.7
C127—C126—H26C	109.5	H12D—C127—H12E	107.6
C273—C126—H26C	111.4	C273—O3B—P1	121.8 (19)
H26A—C126—H26C	109.5	O3B—C273—C126	96.5 (18)
H26B—C126—H26C	109.5	O3B—C273—H27A	112.5
N1B—C201—C202	116.66 (14)	C126—C273—H27A	112.5
N1B—C201—P1B	107.55 (11)	O3B—C273—H27B	112.5
C202—C201—P1B	114.17 (11)	C126—C273—H27B	112.5
N1B—C201—H201	105.9	H27A—C273—H27B	110.0
C202—C201—H201	105.9	C224—O22—P1B	122.6 (9)
P1B—C201—H201	105.9	C225—C224—O22	112.1 (12)
C203—C202—C215	119.74 (15)	C225—C224—H22D	109.2
C203—C202—C201	118.02 (15)	O22—C224—H22D	109.2
C215—C202—C201	122.24 (15)	C225—C224—H22E	109.2
C202—C203—C204	124.16 (17)	O22—C224—H22E	109.2
C202—C203—C208	119.50 (17)	H22D—C224—H22E	107.9
C204—C203—C208	116.33 (17)	C224—C225—H22A	109.5
C205—C204—C203	122.1 (2)	C224—C225—H22B	109.5
C205—C204—H204	119.0	H22A—C225—H22B	109.5
C203—C204—H204	119.0	C224—C225—H22C	109.5
C204—C205—C206	120.9 (2)	H22A—C225—H22C	109.5
C204—C205—H205	119.6	H22B—C225—H22C	109.5
C206—C205—H205	119.6	C229—O22B—P1B	122.6 (9)
C207—C206—C205	120.1 (2)	O22B—C229—C425	101.9 (13)
C207—C206—H206	120.0	O22B—C229—H22F	111.4
C205—C206—H206	120.0	C425—C229—H22F	111.4
C206—C207—C208	121.3 (2)	O22B—C229—H22G	111.4
C206—C207—H207	119.4	C425—C229—H22G	111.4
C208—C207—H207	119.4	H22F—C229—H22G	109.3
C209—C208—C207	121.20 (19)	C229—C425—H42A	109.5
C209—C208—C203	119.44 (17)	C229—C425—H42B	109.5
C207—C208—C203	119.36 (19)	H42A—C425—H42B	109.5
C208—C209—C210	122.40 (17)	C229—C425—H42C	109.5
C208—C209—H209	118.8	H42A—C425—H42C	109.5
C210—C209—H209	118.8	H42B—C425—H42C	109.5
C209—C210—C211	120.74 (18)	O1—P1—O3	116.2 (2)
C209—C210—C215	119.54 (18)	O1—P1—O2B	123.7 (8)
C211—C210—C215	119.71 (19)	O3—P1—O2B	86.3 (10)
C212—C211—C210	121.6 (2)	O1—P1—O2	112.7 (3)
C212—C211—H211	119.2	O3—P1—O2	105.1 (3)
C210—C211—H211	119.2	O1—P1—O3B	109.9 (14)
C211—C212—C213	119.5 (2)	O2B—P1—O3B	101 (2)
C211—C212—H212	120.2	O2—P1—O3B	120 (2)
C213—C212—H212	120.2	O1—P1—C101	113.62 (8)
C214—C213—C212	121.8 (2)	O3—P1—C101	108.5 (3)
C214—C213—H213	119.1	O2B—P1—C101	104.8 (9)
C212—C213—H213	119.1	O2—P1—C101	99.0 (3)
C213—C214—C215	121.6 (2)	O3B—P1—C101	101.0 (11)
C213—C214—H214	119.2	O21—P1B—O22	120.8 (3)
C215—C214—H214	119.2	O21—P1B—O23	114.37 (8)
C202—C215—C214	124.89 (16)	O22—P1B—O23	95.8 (3)
C202—C215—C210	119.31 (16)	O21—P1B—O22B	110.3 (4)
C214—C215—C210	115.81 (17)	O23—P1B—O22B	114.6 (4)
C222—C216—C217	122.05 (18)	O21—P1B—C201	114.42 (8)
C222—C216—H216	119.0	O22—P1B—C201	105.2 (4)
C217—C216—H216	119.0	O23—P1B—C201	103.62 (8)
C216—C217—C218	119.96 (17)	O22B—P1B—C201	98.3 (3)

N1—C101—C102—C103	44.0 (2)	C209—C210—C215—C214	−179.10 (16)
P1—C101—C102—C103	−83.48 (18)	C211—C210—C215—C214	0.7 (2)
N1—C101—C102—C115	−135.43 (17)	C222—C216—C217—C218	0.0 (3)
P1—C101—C102—C115	97.10 (16)	C216—C217—C218—N1B	178.08 (17)
C115—C102—C103—C104	−179.81 (17)	C216—C217—C218—C220	−1.2 (3)
C101—C102—C103—C104	0.8 (3)	N1B—C218—C220—C221	−177.97 (18)
C115—C102—C103—C108	−0.2 (2)	C217—C218—C220—C221	1.4 (3)
C101—C102—C103—C108	−179.66 (15)	C218—C220—C221—C222	−0.3 (3)
C102—C103—C104—C105	179.97 (19)	C217—C216—C222—C221	1.0 (3)
C108—C103—C104—C105	0.4 (3)	C217—C216—C222—C223	−178.1 (2)
C103—C104—C105—C106	0.6 (3)	C220—C221—C222—C216	−0.9 (3)
C104—C105—C106—C107	−1.0 (4)	C220—C221—C222—C223	178.2 (2)
C105—C106—C107—C108	0.4 (4)	C110—C111—C112—C113	−0.5 (4)
C102—C103—C108—C109	−0.2 (3)	C114—C113—C112—C111	−0.4 (4)
C104—C103—C108—C109	179.44 (18)	C120—C118—N1—C101	13.7 (3)
C102—C103—C108—C107	179.46 (18)	C117—C118—N1—C101	−166.66 (17)
C104—C103—C108—C107	−0.9 (3)	C102—C101—N1—C118	59.0 (2)
C106—C107—C108—C109	−179.8 (2)	P1—C101—N1—C118	−171.63 (14)
C106—C107—C108—C103	0.6 (3)	C220—C218—N1B—C201	170.83 (16)
C103—C108—C109—C110	0.1 (3)	C217—C218—N1B—C201	−8.4 (3)
C107—C108—C109—C110	−179.5 (2)	C202—C201—N1B—C218	−62.0 (2)
C108—C109—C110—C111	179.10 (19)	P1B—C201—N1B—C218	168.22 (14)
C108—C109—C110—C115	0.3 (3)	P1—O2—C124—C125	76.8 (12)
C109—C110—C111—C112	−177.8 (2)	P1—O2B—C324—C325	−97 (3)
C115—C110—C111—C112	1.0 (3)	C227—C226—O23—P1B	95.3 (3)
C112—C113—C114—C115	0.8 (3)	C273—C126—C127—O3	−162 (6)
C103—C102—C115—C114	−178.18 (17)	P1—O3—C127—C126	−172.0 (5)
C101—C102—C115—C114	1.2 (3)	P1—O3B—C273—C126	165 (3)
C103—C102—C115—C110	0.7 (2)	C127—C126—C273—O3B	−1 (6)
C101—C102—C115—C110	−179.88 (15)	P1B—O22—C224—C225	168.1 (8)
C113—C114—C115—C102	178.57 (19)	P1B—O22B—C229—C425	−179.2 (8)
C113—C114—C115—C110	−0.3 (3)	C127—O3—P1—O1	−10.1 (10)
C109—C110—C115—C102	−0.7 (3)	C127—O3—P1—O2B	−136.1 (12)
C111—C110—C115—C102	−179.51 (17)	C127—O3—P1—O2	−135.4 (9)
C109—C110—C115—C114	178.23 (18)	C127—O3—P1—O3B	58 (4)
C111—C110—C115—C114	−0.5 (3)	C127—O3—P1—C101	119.5 (9)
C122—C116—C117—C118	−0.6 (3)	C324—O2B—P1—O1	−8 (3)
C116—C117—C118—N1	−179.37 (18)	C324—O2B—P1—O3	112 (2)
C116—C117—C118—C120	0.3 (3)	C324—O2B—P1—O2	−66 (3)
N1—C118—C120—C121	179.37 (17)	C324—O2B—P1—O3B	115 (2)
C117—C118—C120—C121	−0.3 (3)	C324—O2B—P1—C101	−140.3 (19)
C118—C120—C121—C122	0.5 (3)	C124—O2—P1—O1	−88.8 (7)
C120—C121—C122—C116	−0.8 (3)	C124—O2—P1—O3	38.7 (8)
C120—C121—C122—C123	179.8 (2)	C124—O2—P1—O2B	41 (3)
C117—C116—C122—C121	0.8 (3)	C124—O2—P1—O3B	42.6 (13)
C117—C116—C122—C123	−179.8 (2)	C124—O2—P1—C101	150.8 (7)
N1B—C201—C202—C203	139.97 (16)	C273—O3B—P1—O1	26 (4)
P1B—C201—C202—C203	−93.51 (16)	C273—O3B—P1—O3	−92 (5)
N1B—C201—C202—C215	−40.3 (2)	C273—O3B—P1—O2B	−106 (4)
P1B—C201—C202—C215	86.19 (17)	C273—O3B—P1—O2	−106 (3)
C215—C202—C203—C204	−177.95 (16)	C273—O3B—P1—C101	147 (3)
C201—C202—C203—C204	1.8 (2)	N1—C101—P1—O1	48.50 (15)
C215—C202—C203—C208	2.6 (2)	C102—C101—P1—O1	179.49 (12)
C201—C202—C203—C208	−177.73 (14)	N1—C101—P1—O3	−82.5 (2)
C202—C203—C204—C205	−178.87 (18)	C102—C101—P1—O3	48.5 (3)
C208—C203—C204—C205	0.6 (3)	N1—C101—P1—O2B	−173.6 (10)
C203—C204—C205—C206	−0.8 (3)	C102—C101—P1—O2B	−42.6 (10)
C204—C205—C206—C207	0.2 (4)	N1—C101—P1—O2	168.2 (2)
C205—C206—C207—C208	0.6 (3)	C102—C101—P1—O2	−60.9 (3)
C206—C207—C208—C209	179.4 (2)	N1—C101—P1—O3B	−69.1 (19)
C206—C207—C208—C203	−0.7 (3)	C102—C101—P1—O3B	61.9 (19)
C202—C203—C208—C209	−0.5 (2)	C224—O22—P1B—O21	7.4 (14)
C204—C203—C208—C209	179.98 (17)	C224—O22—P1B—O23	130.3 (12)
C202—C203—C208—C207	179.67 (16)	C224—O22—P1B—O22B	−53.0 (19)
C204—C203—C208—C207	0.1 (2)	C224—O22—P1B—C201	−123.9 (12)
C207—C208—C209—C210	178.13 (17)	C226—O23—P1B—O21	12.5 (2)
C203—C208—C209—C210	−1.7 (3)	C226—O23—P1B—O22	−115.1 (4)
C208—C209—C210—C211	−178.03 (17)	C226—O23—P1B—O22B	−116.3 (4)
C208—C209—C210—C215	1.7 (3)	C226—O23—P1B—C201	137.7 (2)
C209—C210—C211—C212	179.3 (2)	C229—O22B—P1B—O21	−65.1 (16)
C215—C210—C211—C212	−0.5 (3)	C229—O22B—P1B—O22	62 (2)
C210—C211—C212—C213	−0.2 (3)	C229—O22B—P1B—O23	65.7 (16)
C211—C212—C213—C214	0.7 (4)	C229—O22B—P1B—C201	174.9 (14)
C212—C213—C214—C215	−0.5 (3)	N1B—C201—P1B—O21	−58.41 (14)
C203—C202—C215—C214	176.93 (16)	C202—C201—P1B—O21	170.46 (12)
C201—C202—C215—C214	−2.8 (2)	N1B—C201—P1B—O22	76.4 (3)
C203—C202—C215—C210	−2.5 (2)	C202—C201—P1B—O22	−54.7 (4)
C201—C202—C215—C210	177.80 (14)	N1B—C201—P1B—O23	176.40 (12)
C213—C214—C215—C202	−179.64 (18)	C202—C201—P1B—O23	45.27 (15)
C213—C214—C215—C210	−0.2 (3)	N1B—C201—P1B—O22B	58.4 (5)
C209—C210—C215—C202	0.4 (2)	C202—C201—P1B—O22B	−72.7 (5)
C211—C210—C215—C202	−179.83 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.98	2.02	2.990 (2)	170
N1B—H1B···O21ⁱⁱ	0.90	2.15	3.016 (2)	163

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

Experimental details

Crystal data
Chemical formula	C₂₆H₂₈NO₃P
M_r	433.46
Crystal system, space group	Triclinic, P1
Temperature (K)	290
a, b, c (Å)	9.5990 (3), 12.6386 (5), 20.2131 (7)
α, β, γ (°)	75.865 (3), 76.780 (4), 74.927 (3)
V (Å³)	2260.13 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.15
Crystal size (mm)	0.31 × 0.18 × 0.15

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.947, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	20827, 12691, 8114
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.704

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.153, 1.02
No. of reflections	12691
No. of parameters	637
No. of restraints	4
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.34

Computer programs: CrysAlis PRO (Agilent, 2010), SHELXS97 (Sheldrick 2008), SHELXL97 (Sheldrick, 2008, ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.98	2.02	2.990 (2)	170
N1B—H1B···O21ⁱⁱ	0.90	2.15	3.016 (2)	163

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

Acknowledgements

Thanks are due to Bulgarian National Science Fund of the Ministry of Education and Science for the financial support [contract DTK 02/34 (2009)].

References

Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Kraicheva, I., Tsacheva, I., Vodenicharova, E., Tashev. E., Tosheva, T., Kril, A., Topashka-Ancheva, M., Iliev, I., Gerassimova, Ts. & Troev, K. (2011). Eur. J. Med. Chem. Submitted. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar