Disopropyl {[(2S,3S)-2-amino-3-methyl­penta­namido](phen­yl)meth­yl}phosphinate

Cheng, H.-M.; Zhang, H.-W.; Fang, H.; Wu, Z.; Zhao, Y.-F.

doi:10.1107/S1600536810051354

organic compounds

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ISSN: 2056-9890

Volume 67| Part 1| January 2011| Page o194

https://doi.org/10.1107/S1600536810051354

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Disopropyl {[(2S,3S)-2-amino-3-methylpentanamido](phenyl)methyl}phosphinate

Hong-Ming Cheng,^a Han-Wen Zhang,^a Hua Fang,^b Zhen Wu ^c and Yu-Fen Zhao ^a ^*

^aDepartment of Chemistry, Key Laboratory for Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, People's Republic of China, ^bThe Third Institute of Oceanography of the State Oceanic Administration, Xiamen 361005, People's Republic of China, and ^cDepartment of Pharmaceutical Science, Medical College, Xiamen University, Xiamen 361005, People's Republic of China
^*Correspondence e-mail: fangmj@xmu.edu.cn

(Received 18 October 2010; accepted 7 December 2010; online 18 December 2010)

There are two independent molecules in the asymmetric unit of the title compound, C₁₉H₃₃N₂O₄P. In the crystal, the two independent molecules are linked via N—H⋯O=P hydrogen bonds, forming dimers.

Related literature

For the biological activity of phosphono-peptides, see: Li et al. (1999 ); Liu et al. (2002 ); Wang et al. (2001 ); Senten et al. (2003 ); Joossens & Van der Veken (2004 ).

Experimental

Crystal data

C₁₉H₃₃N₂O₄P
M_r = 384.44
Monoclinic, P 2₁
a = 9.3455 (3) Å
b = 23.6079 (6) Å
c = 10.0517 (4) Å
β = 103.819 (4)°
V = 2153.49 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.15 mm⁻¹
T = 293 K
0.37 × 0.22 × 0.18 mm

Data collection

Bruker APEX area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.946, T_max = 0.973
7721 measured reflections
6100 independent reflections
4077 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.068
S = 0.82
6100 reflections
469 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.21 e Å⁻³
Absolute structure: Flack (1983 ), 2215 Friedel pairs
Flack parameter: −0.04 (8)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2′ⁱ	0.86	2.07	2.913 (4)	166
N1′—H1′A⋯O2ⁱⁱ	0.86	1.98	2.833 (4)	171
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+1]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+1]$ .

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810051354/su2222sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810051354/su2222Isup2.hkl

checkCIF report

Comment top

In recent years phosphono-peptides have stimulated a great deal of interest due to their considerable biological activities, including antigrowth (Li et al., 1999), antitumoral (Liu et al., 2002), antiviral (Wang et al., 2001), and inhibiton of serine protease effects (Senten et al., 2003 and Joossens et al., 2004).

The title compound crystallized with two independent chiral molecules (A and B) in the asymmetric unit (Fig. 1). They differ only in the chirality of atom C7 (molecule A) and C7' (molecule B).

In the crystal the two independent molecules are linked via N—H···O=P hydrogen bonds, involving the amide unit and a phosphoryl O atom, to form dimers (Table 1).

Related literature top

For the biological activity of phosphono-peptides, see: Li et al. (1999); Liu et al. (2002); Wang et al. (2001); Senten et al. (2003); Joossens & Van der Veken (2004).

Experimental top

To a solution of the starting material, tert-butyl (2S,3S)-1-((isopropoxy(isopropyl)phosphoryl)(phenyl)methylamino) -3-methyl-1-oxopentan-2-ylcarbamate, (1 in scheme), (1 mmol) in dichloromethane (CH₂Cl₂) (10 ml) at 273 K was added trifluoroacetic acid (TFA) (4 ml). After consumption of the starting material (2h), the solvent was then removed under reduced pressure to give a residue, which was extracted with CH₂Cl₂ (3 × 15 ml). The organic phase was dried over anhydrous MgSO₄ and concentrated under vacuum to obtain a slurry residue, which was purified by silica gel column chromatography (petroleum ether/isopropyl alcohol = 35:1) to give the title compound as a colorless amorphous solid. Single crystals of the title compound, suitable for X-ray diffraction analysis, were obtained by slow evaporation of a CH₂Cl₂ solution.

Structure description top

The title compound crystallized with two independent chiral molecules (A and B) in the asymmetric unit (Fig. 1). They differ only in the chirality of atom C7 (molecule A) and C7' (molecule B).

In the crystal the two independent molecules are linked via N—H···O=P hydrogen bonds, involving the amide unit and a phosphoryl O atom, to form dimers (Table 1).

For the biological activity of phosphono-peptides, see: Li et al. (1999); Liu et al. (2002); Wang et al. (2001); Senten et al. (2003); Joossens & Van der Veken (2004).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the two indendent molecules (A and B) of the title compound, with displacement ellipsoids drawn at the 30% probability level. The H-atoms are drawn as spheres of arbitrary radii.
	Fig. 2. The formation of the title compound.

Disopropyl {[(2S,3S)-2-amino-3-methylpentanamido](phenyl)methyl}phosphonate top

Crystal data top

C₁₉H₃₃N₂O₄P	F(000) = 832
M_r = 384.44	D_x = 1.186 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 2328 reflections
a = 9.3455 (3) Å	θ = 2.2–27.4°
b = 23.6079 (6) Å	µ = 0.15 mm⁻¹
c = 10.0517 (4) Å	T = 293 K
β = 103.819 (4)°	Block, colourless
V = 2153.49 (12) Å³	0.37 × 0.22 × 0.18 mm
Z = 4

Data collection top

Bruker APEX area-detector diffractometer	6100 independent reflections
Radiation source: fine-focus sealed tube	4077 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
φ and ω scans	θ_max = 25.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −11→10
T_min = 0.946, T_max = 0.973	k = −28→27
7721 measured reflections	l = −10→11

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)] = 0.043	H-atom parameters constrained
wR(F²) = 0.068	w = 1/[σ²(F_o²) + (0.0212P)²] where P = (F_o² + 2F_c²)/3
S = 0.82	(Δ/σ)_max < 0.001
6100 reflections	Δρ_max = 0.25 e Å⁻³
469 parameters	Δρ_min = −0.21 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 2215 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.04 (8)

Crystal data top

C₁₉H₃₃N₂O₄P	V = 2153.49 (12) Å³
M_r = 384.44	Z = 4
Monoclinic, P2₁	Mo Kα radiation
a = 9.3455 (3) Å	µ = 0.15 mm⁻¹
b = 23.6079 (6) Å	T = 293 K
c = 10.0517 (4) Å	0.37 × 0.22 × 0.18 mm
β = 103.819 (4)°

Data collection top

Bruker APEX area-detector diffractometer	6100 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	4077 reflections with I > 2σ(I)
T_min = 0.946, T_max = 0.973	R_int = 0.028
7721 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	H-atom parameters constrained
wR(F²) = 0.068	Δρ_max = 0.25 e Å⁻³
S = 0.82	Δρ_min = −0.21 e Å⁻³
6100 reflections	Absolute structure: Flack (1983), 2215 Friedel pairs
469 parameters	Absolute structure parameter: −0.04 (8)
1 restraint

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	0.54488 (9)	0.12742 (4)	0.41034 (10)	0.0250 (2)
P1'	0.76424 (10)	0.71698 (4)	0.26570 (11)	0.0290 (2)
O3	0.5955 (2)	0.07253 (9)	0.3476 (3)	0.0301 (6)
O3'	0.8151 (2)	0.77426 (9)	0.2128 (3)	0.0332 (6)
O2	0.5256 (2)	0.12060 (9)	0.5501 (2)	0.0283 (6)
O2'	0.7782 (2)	0.71540 (10)	0.4143 (2)	0.0348 (6)
N1	0.3215 (3)	0.20195 (10)	0.3342 (3)	0.0265 (7)
H1A	0.2822	0.2011	0.4033	0.032*
O4	0.6659 (2)	0.17261 (9)	0.4084 (2)	0.0284 (6)
O1	0.3933 (3)	0.25766 (9)	0.1783 (3)	0.0411 (7)
O4'	0.8531 (2)	0.67185 (9)	0.2055 (3)	0.0318 (6)
N1'	0.5259 (3)	0.64986 (10)	0.1920 (3)	0.0285 (8)
H1'A	0.5203	0.6421	0.2742	0.034*
C7'	0.5793 (3)	0.70512 (12)	0.1630 (4)	0.0266 (9)
H7'A	0.5834	0.7056	0.0665	0.032*
C1'	0.4849 (4)	0.61045 (15)	0.0934 (4)	0.0314 (9)
C7	0.3786 (3)	0.14968 (12)	0.2894 (4)	0.0234 (9)
H7A	0.4048	0.1578	0.2026	0.028*
O1'	0.4953 (3)	0.61820 (11)	−0.0246 (3)	0.0452 (7)
C8'	0.4764 (3)	0.75257 (14)	0.1842 (4)	0.0253 (9)
C14'	0.8065 (4)	0.82932 (15)	0.2768 (4)	0.0371 (10)
H14A	0.7221	0.8299	0.3189	0.045*
C8	0.2625 (4)	0.10308 (13)	0.2619 (4)	0.0261 (9)
C2	0.2534 (4)	0.30147 (13)	0.3222 (4)	0.0336 (10)
H2A	0.1866	0.2859	0.3748	0.040*
C3	0.1619 (3)	0.33578 (13)	0.2048 (4)	0.0277 (9)
H3A	0.2298	0.3545	0.1581	0.033*
C3'	0.5447 (4)	0.50929 (14)	0.1574 (4)	0.0384 (11)
H3'A	0.5721	0.5035	0.0702	0.046*
C1	0.3288 (4)	0.25194 (15)	0.2697 (4)	0.0298 (9)
C9'	0.4235 (4)	0.75559 (14)	0.3020 (4)	0.0341 (10)
H9'A	0.4504	0.7280	0.3694	0.041*
C2'	0.4246 (4)	0.55510 (14)	0.1336 (4)	0.0342 (10)
H2'A	0.3939	0.5609	0.2193	0.041*
C14	0.5785 (4)	0.01592 (14)	0.3957 (5)	0.0405 (11)
H14B	0.5159	0.0171	0.4612	0.049*
C9	0.2107 (4)	0.08209 (15)	0.1318 (5)	0.0458 (11)
H9A	0.2456	0.0966	0.0595	0.055*
C12'	0.3435 (4)	0.83763 (18)	0.1064 (5)	0.0591 (13)
H12A	0.3152	0.8653	0.0394	0.071*
N2	0.3607 (3)	0.33692 (12)	0.4136 (4)	0.0514 (9)
H2B	0.3655	0.3725	0.3969	0.062*
H2C	0.4194	0.3223	0.4844	0.062*
C5	0.0744 (4)	0.38135 (14)	0.2554 (4)	0.0449 (11)
H5A	0.1355	0.3985	0.3372	0.054*
H5B	−0.0098	0.3641	0.2804	0.054*
N2'	0.2973 (3)	0.53769 (12)	0.0285 (4)	0.0572 (11)
H2'B	0.2672	0.5582	−0.0435	0.069*
H2'C	0.2519	0.5068	0.0380	0.069*
C5'	0.4878 (5)	0.45359 (15)	0.1966 (5)	0.0617 (14)
H5'A	0.4002	0.4435	0.1272	0.074*
H5'B	0.4588	0.4586	0.2822	0.074*
C10'	0.3322 (4)	0.79868 (15)	0.3199 (4)	0.0397 (10)
H10A	0.2963	0.7999	0.3986	0.048*
C6	0.0196 (4)	0.42788 (15)	0.1484 (5)	0.0558 (13)
H6A	−0.0365	0.4553	0.1851	0.084*
H6B	−0.0414	0.4113	0.0673	0.084*
H6C	0.1025	0.4462	0.1260	0.084*
C17	0.7184 (4)	0.19043 (14)	0.2890 (4)	0.0378 (10)
H17A	0.6411	0.1839	0.2055	0.045*
C13'	0.4373 (4)	0.79381 (15)	0.0870 (4)	0.0392 (10)
H13A	0.4729	0.7928	0.0081	0.047*
C4	0.0620 (4)	0.29675 (15)	0.1011 (4)	0.0440 (11)
H4A	0.1211	0.2692	0.0687	0.066*
H4B	0.0081	0.3188	0.0253	0.066*
H4C	−0.0058	0.2778	0.1443	0.066*
C13	0.2073 (4)	0.08177 (15)	0.3678 (4)	0.0391 (11)
H13B	0.2390	0.0966	0.4557	0.047*
C18'	1.0836 (4)	0.67632 (19)	0.1413 (5)	0.0633 (14)
H18A	1.0643	0.7143	0.1077	0.095*
H18B	1.0433	0.6500	0.0694	0.095*
H18C	1.1881	0.6706	0.1715	0.095*
C11'	0.2934 (4)	0.83991 (17)	0.2233 (5)	0.0507 (12)
H11A	0.2329	0.8696	0.2368	0.061*
C17'	1.0145 (4)	0.66720 (16)	0.2576 (4)	0.0400 (10)
H17B	1.0494	0.6959	0.3284	0.048*
C11	0.0566 (4)	0.01705 (18)	0.2126 (6)	0.0605 (14)
H11B	−0.0106	−0.0127	0.1958	0.073*
C16	0.7231 (5)	−0.00693 (16)	0.4637 (6)	0.090 (2)
H16A	0.7652	0.0155	0.5430	0.136*
H16B	0.7867	−0.0060	0.4015	0.136*
H16C	0.7123	−0.0453	0.4911	0.136*
C15	0.5065 (5)	−0.02030 (18)	0.2762 (6)	0.094 (2)
H15A	0.4094	−0.0061	0.2366	0.141*
H15B	0.4999	−0.0586	0.3065	0.141*
H15C	0.5641	−0.0194	0.2089	0.141*
C6'	0.5957 (5)	0.40500 (16)	0.2128 (6)	0.097 (2)
H6'A	0.5496	0.3711	0.2348	0.145*
H6'B	0.6805	0.4134	0.2851	0.145*
H6'C	0.6256	0.3996	0.1287	0.145*
C19	0.7503 (4)	0.25248 (15)	0.3056 (5)	0.0517 (12)
H19A	0.6606	0.2727	0.3031	0.078*
H19B	0.7920	0.2655	0.2325	0.078*
H19C	0.8189	0.2591	0.3918	0.078*
C15'	0.9436 (4)	0.83977 (18)	0.3822 (4)	0.0576 (13)
H15D	0.9513	0.8130	0.4554	0.086*
H15E	0.9421	0.8775	0.4174	0.086*
H15F	1.0267	0.8356	0.3423	0.086*
C19'	1.0489 (4)	0.60907 (16)	0.3168 (5)	0.0689 (15)
H19D	1.0076	0.6047	0.3950	0.103*
H19E	1.1538	0.6041	0.3442	0.103*
H19F	1.0072	0.5812	0.2490	0.103*
C16'	0.7826 (5)	0.87172 (15)	0.1608 (5)	0.0604 (14)
H16D	0.6898	0.8644	0.0978	0.091*
H16E	0.8605	0.8684	0.1141	0.091*
H16F	0.7823	0.9093	0.1971	0.091*
C12	0.1044 (4)	0.03818 (17)	0.3426 (5)	0.0515 (12)
H12B	0.0680	0.0234	0.4137	0.062*
C10	0.1072 (5)	0.03950 (19)	0.1086 (5)	0.0602 (13)
H10B	0.0715	0.0259	0.0200	0.072*
C4'	0.6813 (4)	0.52743 (15)	0.2605 (5)	0.0594 (14)
H4'A	0.7552	0.4985	0.2690	0.089*
H4'B	0.6585	0.5333	0.3476	0.089*
H4'C	0.7177	0.5620	0.2306	0.089*
C18	0.8524 (4)	0.15616 (16)	0.2835 (5)	0.0625 (15)
H18D	0.8254	0.1170	0.2686	0.094*
H18E	0.9249	0.1600	0.3685	0.094*
H18F	0.8925	0.1696	0.2098	0.094*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P1	0.0293 (5)	0.0232 (5)	0.0231 (6)	0.0013 (4)	0.0075 (5)	−0.0012 (5)
P1'	0.0313 (5)	0.0299 (6)	0.0274 (7)	−0.0014 (5)	0.0100 (5)	0.0004 (5)
O3	0.0392 (13)	0.0222 (13)	0.0314 (17)	0.0077 (11)	0.0134 (13)	0.0018 (12)
O3'	0.0485 (15)	0.0234 (14)	0.0322 (17)	−0.0054 (12)	0.0186 (14)	−0.0032 (13)
O2	0.0369 (13)	0.0296 (14)	0.0209 (15)	0.0029 (11)	0.0117 (12)	−0.0018 (13)
O2'	0.0434 (14)	0.0386 (14)	0.0243 (15)	−0.0068 (13)	0.0114 (13)	0.0001 (14)
N1	0.0382 (17)	0.0211 (17)	0.0247 (19)	0.0043 (13)	0.0167 (16)	0.0048 (15)
O4	0.0338 (13)	0.0297 (13)	0.0244 (16)	−0.0032 (11)	0.0121 (13)	−0.0035 (12)
O1	0.0585 (17)	0.0320 (16)	0.043 (2)	0.0109 (13)	0.0331 (16)	0.0119 (14)
O4'	0.0282 (13)	0.0339 (14)	0.0335 (17)	0.0039 (11)	0.0074 (13)	−0.0028 (13)
N1'	0.0366 (16)	0.0302 (18)	0.0180 (19)	−0.0070 (13)	0.0049 (16)	0.0008 (15)
C7'	0.0359 (19)	0.025 (2)	0.022 (2)	−0.0058 (17)	0.0134 (18)	0.0030 (18)
C1'	0.030 (2)	0.034 (2)	0.031 (3)	0.0018 (17)	0.009 (2)	−0.002 (2)
C7	0.0307 (19)	0.023 (2)	0.018 (2)	0.0045 (15)	0.0107 (18)	−0.0022 (17)
O1'	0.0679 (18)	0.0463 (17)	0.0259 (17)	−0.0096 (14)	0.0199 (15)	−0.0034 (15)
C8'	0.0240 (19)	0.028 (2)	0.024 (3)	−0.0037 (16)	0.0054 (19)	0.0019 (19)
C14'	0.038 (2)	0.031 (2)	0.047 (3)	−0.0045 (18)	0.019 (2)	−0.005 (2)
C8	0.0291 (19)	0.023 (2)	0.026 (2)	0.0018 (16)	0.0051 (19)	0.0037 (18)
C2	0.039 (2)	0.023 (2)	0.043 (3)	0.0058 (17)	0.020 (2)	0.001 (2)
C3	0.034 (2)	0.0202 (19)	0.033 (3)	0.0032 (17)	0.0156 (19)	0.0034 (18)
C3'	0.052 (2)	0.029 (2)	0.039 (3)	−0.0053 (19)	0.023 (2)	−0.004 (2)
C1	0.033 (2)	0.027 (2)	0.033 (3)	0.0044 (18)	0.016 (2)	0.001 (2)
C9'	0.036 (2)	0.031 (2)	0.036 (3)	0.0073 (18)	0.010 (2)	0.006 (2)
C2'	0.037 (2)	0.032 (2)	0.036 (3)	−0.0107 (18)	0.015 (2)	−0.002 (2)
C14	0.058 (3)	0.019 (2)	0.057 (3)	0.002 (2)	0.038 (3)	0.003 (2)
C9	0.050 (2)	0.041 (2)	0.044 (3)	−0.008 (2)	0.006 (2)	−0.013 (2)
C12'	0.063 (3)	0.058 (3)	0.064 (4)	0.025 (2)	0.030 (3)	0.028 (3)
N2	0.065 (2)	0.0335 (19)	0.045 (3)	0.0142 (17)	−0.0096 (19)	−0.0124 (18)
C5	0.056 (2)	0.030 (2)	0.052 (3)	0.0140 (19)	0.018 (2)	0.004 (2)
N2'	0.059 (2)	0.040 (2)	0.061 (3)	−0.0297 (17)	−0.010 (2)	0.007 (2)
C5'	0.076 (3)	0.039 (3)	0.080 (4)	0.002 (2)	0.038 (3)	0.002 (3)
C10'	0.035 (2)	0.045 (2)	0.040 (3)	0.0044 (19)	0.012 (2)	−0.003 (2)
C6	0.055 (3)	0.039 (3)	0.075 (4)	0.018 (2)	0.020 (3)	0.016 (3)
C17	0.040 (2)	0.043 (2)	0.034 (3)	−0.0089 (18)	0.017 (2)	−0.002 (2)
C13'	0.038 (2)	0.046 (2)	0.040 (3)	0.006 (2)	0.020 (2)	0.007 (2)
C4	0.036 (2)	0.045 (2)	0.051 (3)	0.0009 (19)	0.011 (2)	−0.003 (2)
C13	0.034 (2)	0.041 (2)	0.040 (3)	−0.0028 (19)	0.002 (2)	−0.001 (2)
C18'	0.047 (3)	0.080 (3)	0.068 (4)	0.007 (2)	0.024 (3)	0.009 (3)
C11'	0.041 (2)	0.047 (3)	0.064 (4)	0.015 (2)	0.014 (3)	0.002 (3)
C17'	0.029 (2)	0.041 (2)	0.047 (3)	0.0018 (18)	0.004 (2)	−0.004 (2)
C11	0.037 (3)	0.044 (3)	0.094 (5)	−0.012 (2)	0.001 (3)	−0.008 (3)
C16	0.099 (4)	0.040 (3)	0.097 (5)	0.016 (3)	−0.046 (3)	0.004 (3)
C15	0.080 (4)	0.042 (3)	0.140 (6)	0.007 (3)	−0.016 (4)	−0.027 (3)
C6'	0.126 (4)	0.037 (3)	0.165 (7)	0.016 (3)	0.106 (5)	0.019 (3)
C19	0.056 (3)	0.040 (2)	0.066 (4)	−0.002 (2)	0.028 (3)	0.012 (2)
C15'	0.058 (3)	0.067 (3)	0.049 (3)	−0.013 (2)	0.015 (3)	−0.020 (3)
C19'	0.056 (3)	0.061 (3)	0.080 (4)	0.006 (2)	−0.001 (3)	0.018 (3)
C16'	0.079 (3)	0.029 (2)	0.080 (4)	0.002 (2)	0.033 (3)	0.004 (3)
C12	0.040 (2)	0.056 (3)	0.057 (4)	−0.013 (2)	0.008 (3)	0.011 (3)
C10	0.056 (3)	0.067 (3)	0.055 (4)	−0.012 (3)	0.009 (3)	−0.020 (3)
C4'	0.052 (3)	0.038 (2)	0.078 (4)	0.010 (2)	−0.003 (3)	−0.001 (3)
C18	0.057 (3)	0.061 (3)	0.086 (4)	0.003 (2)	0.051 (3)	0.008 (3)

Geometric parameters (Å, º) top

P1—O2	1.467 (2)	C5—H5B	0.9700
P1—O4	1.558 (2)	N2'—H2'B	0.8600
P1—O3	1.563 (2)	N2'—H2'C	0.8600
P1—C7	1.807 (3)	C5'—C6'	1.510 (5)
P1'—O2'	1.469 (2)	C5'—H5'A	0.9700
P1'—O4'	1.559 (2)	C5'—H5'B	0.9700
P1'—O3'	1.568 (2)	C10'—C11'	1.362 (5)
P1'—C7'	1.810 (3)	C10'—H10A	0.9300
O3—C14	1.443 (4)	C6—H6A	0.9600
O3'—C14'	1.461 (4)	C6—H6B	0.9600
N1—C1	1.356 (4)	C6—H6C	0.9600
N1—C7	1.458 (4)	C17—C19	1.496 (4)
N1—H1A	0.8600	C17—C18	1.503 (5)
O4—C17	1.463 (4)	C17—H17A	0.9800
O1—C1	1.220 (4)	C13'—H13A	0.9300
O4'—C17'	1.478 (4)	C4—H4A	0.9600
N1'—C1'	1.346 (4)	C4—H4B	0.9600
N1'—C7'	1.451 (4)	C4—H4C	0.9600
N1'—H1'A	0.8600	C13—C12	1.390 (5)
C7'—C8'	1.524 (4)	C13—H13B	0.9300
C7'—H7'A	0.9800	C18'—C17'	1.480 (6)
C1'—O1'	1.227 (4)	C18'—H18A	0.9600
C1'—C2'	1.515 (5)	C18'—H18B	0.9600
C7—C8	1.524 (4)	C18'—H18C	0.9600
C7—H7A	0.9800	C11'—H11A	0.9300
C8'—C13'	1.366 (5)	C17'—C19'	1.500 (5)
C8'—C9'	1.390 (5)	C17'—H17B	0.9800
C14'—C15'	1.475 (5)	C11—C10	1.355 (7)
C14'—C16'	1.512 (5)	C11—C12	1.369 (7)
C14'—H14A	0.9800	C11—H11B	0.9300
C8—C9	1.374 (5)	C16—H16A	0.9600
C8—C13	1.384 (5)	C16—H16B	0.9600
C2—N2	1.452 (4)	C16—H16C	0.9600
C2—C3	1.516 (5)	C15—H15A	0.9600
C2—C1	1.523 (5)	C15—H15B	0.9600
C2—H2A	0.9800	C15—H15C	0.9600
C3—C5	1.511 (4)	C6'—H6'A	0.9600
C3—C4	1.530 (5)	C6'—H6'B	0.9600
C3—H3A	0.9800	C6'—H6'C	0.9600
C3'—C4'	1.502 (5)	C19—H19A	0.9600
C3'—C5'	1.506 (5)	C19—H19B	0.9600
C3'—C2'	1.536 (5)	C19—H19C	0.9600
C3'—H3'A	0.9800	C15'—H15D	0.9600
C9'—C10'	1.367 (4)	C15'—H15E	0.9600
C9'—H9'A	0.9300	C15'—H15F	0.9600
C2'—N2'	1.450 (4)	C19'—H19D	0.9600
C2'—H2'A	0.9800	C19'—H19E	0.9600
C14—C16	1.464 (5)	C19'—H19F	0.9600
C14—C15	1.496 (6)	C16'—H16D	0.9600
C14—H14B	0.9800	C16'—H16E	0.9600
C9—C10	1.376 (5)	C16'—H16F	0.9600
C9—H9A	0.9300	C12—H12B	0.9300
C12'—C11'	1.366 (6)	C10—H10B	0.9300
C12'—C13'	1.399 (5)	C4'—H4'A	0.9600
C12'—H12A	0.9300	C4'—H4'B	0.9600
N2—H2B	0.8600	C4'—H4'C	0.9600
N2—H2C	0.8600	C18—H18D	0.9600
C5—C6	1.537 (5)	C18—H18E	0.9600
C5—H5A	0.9700	C18—H18F	0.9600

O2—P1—O4	110.01 (14)	C6'—C5'—H5'B	108.5
O2—P1—O3	114.41 (14)	H5'A—C5'—H5'B	107.5
O4—P1—O3	105.78 (12)	C11'—C10'—C9'	120.4 (4)
O2—P1—C7	113.18 (14)	C11'—C10'—H10A	119.8
O4—P1—C7	107.63 (14)	C9'—C10'—H10A	119.8
O3—P1—C7	105.33 (14)	C5—C6—H6A	109.5
O2'—P1'—O4'	116.83 (13)	C5—C6—H6B	109.5
O2'—P1'—O3'	113.99 (13)	H6A—C6—H6B	109.5
O4'—P1'—O3'	103.00 (13)	C5—C6—H6C	109.5
O2'—P1'—C7'	114.64 (16)	H6A—C6—H6C	109.5
O4'—P1'—C7'	101.38 (14)	H6B—C6—H6C	109.5
O3'—P1'—C7'	105.38 (14)	O4—C17—C19	106.7 (3)
C14—O3—P1	124.4 (2)	O4—C17—C18	108.7 (3)
C14'—O3'—P1'	124.4 (2)	C19—C17—C18	112.7 (3)
C1—N1—C7	121.7 (3)	O4—C17—H17A	109.6
C1—N1—H1A	119.2	C19—C17—H17A	109.6
C7—N1—H1A	119.2	C18—C17—H17A	109.6
C17—O4—P1	126.4 (2)	C8'—C13'—C12'	119.8 (4)
C17'—O4'—P1'	120.4 (2)	C8'—C13'—H13A	120.1
C1'—N1'—C7'	121.6 (3)	C12'—C13'—H13A	120.1
C1'—N1'—H1'A	119.2	C3—C4—H4A	109.5
C7'—N1'—H1'A	119.2	C3—C4—H4B	109.5
N1'—C7'—C8'	111.9 (3)	H4A—C4—H4B	109.5
N1'—C7'—P1'	110.6 (2)	C3—C4—H4C	109.5
C8'—C7'—P1'	110.8 (2)	H4A—C4—H4C	109.5
N1'—C7'—H7'A	107.8	H4B—C4—H4C	109.5
C8'—C7'—H7'A	107.8	C8—C13—C12	119.8 (4)
P1'—C7'—H7'A	107.8	C8—C13—H13B	120.1
O1'—C1'—N1'	122.3 (3)	C12—C13—H13B	120.1
O1'—C1'—C2'	120.4 (4)	C17'—C18'—H18A	109.5
N1'—C1'—C2'	117.3 (3)	C17'—C18'—H18B	109.5
N1—C7—C8	111.7 (3)	H18A—C18'—H18B	109.5
N1—C7—P1	111.0 (2)	C17'—C18'—H18C	109.5
C8—C7—P1	111.9 (2)	H18A—C18'—H18C	109.5
N1—C7—H7A	107.3	H18B—C18'—H18C	109.5
C8—C7—H7A	107.3	C10'—C11'—C12'	119.9 (4)
P1—C7—H7A	107.3	C10'—C11'—H11A	120.1
C13'—C8'—C9'	118.9 (3)	C12'—C11'—H11A	120.1
C13'—C8'—C7'	119.6 (3)	O4'—C17'—C18'	108.1 (3)
C9'—C8'—C7'	121.4 (3)	O4'—C17'—C19'	108.2 (3)
O3'—C14'—C15'	109.6 (3)	C18'—C17'—C19'	110.7 (3)
O3'—C14'—C16'	105.2 (3)	O4'—C17'—H17B	109.9
C15'—C14'—C16'	112.7 (3)	C18'—C17'—H17B	109.9
O3'—C14'—H14A	109.7	C19'—C17'—H17B	109.9
C15'—C14'—H14A	109.7	C10—C11—C12	119.9 (4)
C16'—C14'—H14A	109.7	C10—C11—H11B	120.0
C9—C8—C13	119.3 (3)	C12—C11—H11B	120.0
C9—C8—C7	120.4 (4)	C14—C16—H16A	109.5
C13—C8—C7	120.2 (4)	C14—C16—H16B	109.5
N2—C2—C3	111.1 (3)	H16A—C16—H16B	109.5
N2—C2—C1	110.8 (3)	C14—C16—H16C	109.5
C3—C2—C1	111.2 (3)	H16A—C16—H16C	109.5
N2—C2—H2A	107.9	H16B—C16—H16C	109.5
C3—C2—H2A	107.9	C14—C15—H15A	109.5
C1—C2—H2A	107.9	C14—C15—H15B	109.5
C5—C3—C2	111.6 (3)	H15A—C15—H15B	109.5
C5—C3—C4	111.5 (3)	C14—C15—H15C	109.5
C2—C3—C4	110.3 (3)	H15A—C15—H15C	109.5
C5—C3—H3A	107.7	H15B—C15—H15C	109.5
C2—C3—H3A	107.7	C5'—C6'—H6'A	109.5
C4—C3—H3A	107.7	C5'—C6'—H6'B	109.5
C4'—C3'—C5'	111.3 (4)	H6'A—C6'—H6'B	109.5
C4'—C3'—C2'	112.1 (3)	C5'—C6'—H6'C	109.5
C5'—C3'—C2'	111.4 (3)	H6'A—C6'—H6'C	109.5
C4'—C3'—H3'A	107.2	H6'B—C6'—H6'C	109.5
C5'—C3'—H3'A	107.2	C17—C19—H19A	109.5
C2'—C3'—H3'A	107.2	C17—C19—H19B	109.5
O1—C1—N1	123.1 (3)	H19A—C19—H19B	109.5
O1—C1—C2	121.9 (3)	C17—C19—H19C	109.5
N1—C1—C2	115.0 (3)	H19A—C19—H19C	109.5
C10'—C9'—C8'	120.7 (4)	H19B—C19—H19C	109.5
C10'—C9'—H9'A	119.7	C14'—C15'—H15D	109.5
C8'—C9'—H9'A	119.7	C14'—C15'—H15E	109.5
N2'—C2'—C1'	110.0 (3)	H15D—C15'—H15E	109.5
N2'—C2'—C3'	110.8 (3)	C14'—C15'—H15F	109.5
C1'—C2'—C3'	110.2 (3)	H15D—C15'—H15F	109.5
N2'—C2'—H2'A	108.6	H15E—C15'—H15F	109.5
C1'—C2'—H2'A	108.6	C17'—C19'—H19D	109.5
C3'—C2'—H2'A	108.6	C17'—C19'—H19E	109.5
O3—C14—C16	109.5 (3)	H19D—C19'—H19E	109.5
O3—C14—C15	109.0 (4)	C17'—C19'—H19F	109.5
C16—C14—C15	110.6 (3)	H19D—C19'—H19F	109.5
O3—C14—H14B	109.2	H19E—C19'—H19F	109.5
C16—C14—H14B	109.2	C14'—C16'—H16D	109.5
C15—C14—H14B	109.2	C14'—C16'—H16E	109.5
C8—C9—C10	119.9 (4)	H16D—C16'—H16E	109.5
C8—C9—H9A	120.1	C14'—C16'—H16F	109.5
C10—C9—H9A	120.1	H16D—C16'—H16F	109.5
C11'—C12'—C13'	120.3 (4)	H16E—C16'—H16F	109.5
C11'—C12'—H12A	119.9	C11—C12—C13	119.8 (5)
C13'—C12'—H12A	119.9	C11—C12—H12B	120.1
C2—N2—H2B	120.0	C13—C12—H12B	120.1
C2—N2—H2C	120.0	C11—C10—C9	121.1 (5)
H2B—N2—H2C	120.0	C11—C10—H10B	119.5
C3—C5—C6	112.9 (3)	C9—C10—H10B	119.5
C3—C5—H5A	109.0	C3'—C4'—H4'A	109.5
C6—C5—H5A	109.0	C3'—C4'—H4'B	109.5
C3—C5—H5B	109.0	H4'A—C4'—H4'B	109.5
C6—C5—H5B	109.0	C3'—C4'—H4'C	109.5
H5A—C5—H5B	107.8	H4'A—C4'—H4'C	109.5
C2'—N2'—H2'B	120.0	H4'B—C4'—H4'C	109.5
C2'—N2'—H2'C	120.0	C17—C18—H18D	109.5
H2'B—N2'—H2'C	120.0	C17—C18—H18E	109.5
C3'—C5'—C6'	115.0 (3)	H18D—C18—H18E	109.5
C3'—C5'—H5'A	108.5	C17—C18—H18F	109.5
C6'—C5'—H5'A	108.5	H18D—C18—H18F	109.5
C3'—C5'—H5'B	108.5	H18E—C18—H18F	109.5

O2—P1—O3—C14	20.4 (3)	N2—C2—C3—C4	173.5 (3)
O4—P1—O3—C14	141.7 (3)	C1—C2—C3—C4	49.6 (4)
C7—P1—O3—C14	−104.5 (3)	C7—N1—C1—O1	−6.1 (5)
O2'—P1'—O3'—C14'	−29.8 (3)	C7—N1—C1—C2	175.4 (3)
O4'—P1'—O3'—C14'	−157.4 (3)	N2—C2—C1—O1	−78.0 (5)
C7'—P1'—O3'—C14'	96.7 (3)	C3—C2—C1—O1	46.1 (5)
O2—P1—O4—C17	178.8 (2)	N2—C2—C1—N1	100.6 (4)
O3—P1—O4—C17	54.8 (3)	C3—C2—C1—N1	−135.3 (3)
C7—P1—O4—C17	−57.5 (3)	C13'—C8'—C9'—C10'	0.8 (5)
O2'—P1'—O4'—C17'	−56.4 (3)	C7'—C8'—C9'—C10'	179.5 (3)
O3'—P1'—O4'—C17'	69.4 (3)	O1'—C1'—C2'—N2'	−42.7 (5)
C7'—P1'—O4'—C17'	178.3 (3)	N1'—C1'—C2'—N2'	137.5 (3)
C1'—N1'—C7'—C8'	115.2 (3)	O1'—C1'—C2'—C3'	79.8 (4)
C1'—N1'—C7'—P1'	−120.7 (3)	N1'—C1'—C2'—C3'	−100.0 (4)
O2'—P1'—C7'—N1'	−60.2 (3)	C4'—C3'—C2'—N2'	176.9 (3)
O4'—P1'—C7'—N1'	66.6 (3)	C5'—C3'—C2'—N2'	−57.6 (5)
O3'—P1'—C7'—N1'	173.6 (2)	C4'—C3'—C2'—C1'	54.9 (5)
O2'—P1'—C7'—C8'	64.5 (3)	C5'—C3'—C2'—C1'	−179.6 (3)
O4'—P1'—C7'—C8'	−168.7 (2)	P1—O3—C14—C16	−109.8 (4)
O3'—P1'—C7'—C8'	−61.6 (3)	P1—O3—C14—C15	129.1 (3)
C7'—N1'—C1'—O1'	2.7 (5)	C13—C8—C9—C10	−1.3 (6)
C7'—N1'—C1'—C2'	−177.5 (3)	C7—C8—C9—C10	179.2 (3)
C1—N1—C7—C8	−125.8 (3)	C2—C3—C5—C6	162.1 (3)
C1—N1—C7—P1	108.6 (3)	C4—C3—C5—C6	−74.0 (4)
O2—P1—C7—N1	55.9 (3)	C4'—C3'—C5'—C6'	−58.0 (5)
O4—P1—C7—N1	−65.9 (2)	C2'—C3'—C5'—C6'	176.1 (4)
O3—P1—C7—N1	−178.4 (2)	C8'—C9'—C10'—C11'	−1.0 (6)
O2—P1—C7—C8	−69.6 (3)	P1—O4—C17—C19	144.1 (2)
O4—P1—C7—C8	168.6 (2)	P1—O4—C17—C18	−94.2 (3)
O3—P1—C7—C8	56.1 (3)	C9'—C8'—C13'—C12'	−0.9 (5)
N1'—C7'—C8'—C13'	−133.4 (3)	C7'—C8'—C13'—C12'	−179.6 (3)
P1'—C7'—C8'—C13'	102.7 (3)	C11'—C12'—C13'—C8'	1.3 (6)
N1'—C7'—C8'—C9'	48.0 (4)	C9—C8—C13—C12	2.2 (5)
P1'—C7'—C8'—C9'	−76.0 (4)	C7—C8—C13—C12	−178.2 (3)
P1'—O3'—C14'—C15'	89.5 (3)	C9'—C10'—C11'—C12'	1.3 (6)
P1'—O3'—C14'—C16'	−149.1 (2)	C13'—C12'—C11'—C10'	−1.5 (7)
N1—C7—C8—C9	115.1 (4)	P1'—O4'—C17'—C18'	−121.1 (3)
P1—C7—C8—C9	−119.8 (3)	P1'—O4'—C17'—C19'	118.9 (3)
N1—C7—C8—C13	−64.4 (4)	C10—C11—C12—C13	−1.4 (7)
P1—C7—C8—C13	60.7 (4)	C8—C13—C12—C11	−0.9 (6)
N2—C2—C3—C5	−61.9 (4)	C12—C11—C10—C9	2.4 (7)
C1—C2—C3—C5	174.2 (3)	C8—C9—C10—C11	−1.0 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2′ⁱ	0.86	2.07	2.913 (4)	166
N1′—H1′A···O2ⁱⁱ	0.86	1.98	2.833 (4)	171

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

Experimental details

Crystal data
Chemical formula	C₁₉H₃₃N₂O₄P
M_r	384.44
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	293
a, b, c (Å)	9.3455 (3), 23.6079 (6), 10.0517 (4)
β (°)	103.819 (4)
V (Å³)	2153.49 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.15
Crystal size (mm)	0.37 × 0.22 × 0.18

Data collection
Diffractometer	Bruker APEX area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.946, 0.973
No. of measured, independent and observed [I > 2σ(I)] reflections	7721, 6100, 4077
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.068, 0.82
No. of reflections	6100
No. of parameters	469
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.21
Absolute structure	Flack (1983), 2215 Friedel pairs
Absolute structure parameter	−0.04 (8)

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPIII (Farrugia, 1997) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2'ⁱ	0.86	2.07	2.913 (4)	166
N1'—H1'A···O2ⁱⁱ	0.86	1.98	2.833 (4)	171

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

Acknowledgements

Financial support from the Major Program of the National Natural Science Foundation of China (20732004) and the General Programs of the National Natural Science Foundation of China (20972130 and 40806032) is gratefully acknowledged.

References

Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Joossens, J. & Van der Veken, P. (2004). J. Med. Chem. 47, 2411–2413. Web of Science CrossRef PubMed CAS Google Scholar
Li, Z. G., Huang, R. Q. & Yang, Z. L. (1999). Chin. J. Appl. Chem. 2, 90–92. Google Scholar
Liu, X. J., Chen, R. Y. & Yang, Y. Y. (2002). Chem. J. Chin. Univ. 23, 1299–1303. CAS Google Scholar
Senten, K., Daniels, L. & Van der Veken, P. (2003). J. Comb. Chem. 5, 336–344. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, Q. M., Li, Z. G., Huang, R. Q. & Cheng, J. R. (2001). Heteroat. Chem. 12, 68–72. Web of Science CrossRef Google Scholar

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

Diso­propyl {[(2S,3S)-2-amino-3-methyl­penta­namido](phen­yl)meth­yl}phosphinate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Disopropyl {[(2S,3S)-2-amino-3-methylpentanamido](phenyl)methyl}phosphinate