Literature DB >> 23476271

Diphenyl (isopropyl-amido)-phosphate.

Fahimeh Sabbaghi¹, Mehrdad Pourayoubi, Marek Nečas, Michal Babiak.

Abstract

The P atom in the title compound, C15H18NO3P, is in a distorted tetra-hedral P(O)(O)2N environment; the bond angles at P are in the range 98.16 (6)-115.82 (6)°. In the crystal, adjacent mol-ecules are linked via N-H⋯O=P hydrogen bonds into a chain running parallel to the b axis. The methyl groups are disordered over two sets of sites in a 0.677 (14):0.323 (14) ratio. The crystal studied was a non-merohedral twin with a refined minor component of 22.31 (4)%.

Entities: CellLine Chemical Disease Gene

Year: 2012 PMID： 23476271 PMCID： PMC3589035 DOI： 10.1107/S1600536812047940

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For bond lengths and angles in a related structure, see: Sabbaghi et al. (2011 ▶).

Experimental

Crystal data

C15H18NO3P M = 291.27 Monoclinic, a = 8.4432 (5) Å b = 5.3030 (4) Å c = 16.3443 (11) Å β = 90.453 (6)° V = 731.78 (9) Å3 Z = 2 Mo Kα radiation μ = 0.19 mm−1 T = 120 K 0.45 × 0.42 × 0.40 mm

Data collection

Oxford Diffraction Xcalibur (Sapphire2) diffractometer Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.918, T max = 0.926 6226 measured reflections 6226 independent reflections 6040 reflections with I > 2σ(I)

Refinement

R[F 2 > 2σ(F 2)] = 0.027 wR(F 2) = 0.081 S = 1.06 6226 reflections 208 parameters 28 restraints H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.17 e Å−3 Δρmin = −0.18 e Å−3 Absolute structure: Flack (1983 ▶), 1229 Friedel pairs Flack parameter: 0.05 (6) Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶) and enCIFer (Allen et al., 2004 ▶). Click here for additional data file. Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812047940/ff2090sup1.cif Click here for additional data file. Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812047940/ff2090Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₅H₁₈NO₃P	F(000) = 308
M_r = 291.27	D_x = 1.322 Mg m⁻³
Monoclinic, Pn	Mo Kα radiation, λ = 0.71073 Å
a = 8.4432 (5) Å	Cell parameters from 3821 reflections
b = 5.3030 (4) Å	θ = 3.4–27.5°
c = 16.3443 (11) Å	µ = 0.19 mm⁻¹
β = 90.453 (6)°	T = 120 K
V = 731.78 (9) Å³	Block, colourless
Z = 2	0.45 × 0.42 × 0.40 mm

Oxford Diffraction Xcalibur (Sapphire2) diffractometer	6226 independent reflections
Radiation source: Enhance (Mo) X-ray Source	6040 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.000
Detector resolution: 8.4353 pixels mm^-1	θ_max = 25.0°, θ_min = 3.8°
ω scan	h = −10→10
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	k = −6→6
T_min = 0.918, T_max = 0.926	l = −19→19
6226 measured reflections

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)] = 0.027	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.081	w = 1/[σ²(F_o²) + (0.0626P)² + 0.0183P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
6226 reflections	Δρ_max = 0.17 e Å⁻³
208 parameters	Δρ_min = −0.18 e Å⁻³
28 restraints	Absolute structure: Flack (1983), 1229 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.05 (6)

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	U_iso*/U_eq	Occ. (<1)
P1	0.49359 (4)	0.20465 (6)	0.51025 (3)	0.01893 (9)
O1	0.46890 (12)	0.20756 (19)	0.41396 (6)	0.0229 (3)
O2	0.32869 (12)	0.3259 (2)	0.53519 (6)	0.0213 (2)
O3	0.52704 (12)	−0.04455 (19)	0.54422 (6)	0.0247 (3)
N1	0.62616 (15)	0.4126 (2)	0.53057 (8)	0.0201 (3)
H1N	0.603 (2)	0.559 (3)	0.5224 (10)	0.024*
C1	0.33996 (19)	0.0959 (3)	0.37348 (10)	0.0241 (4)
C2	0.2687 (2)	−0.1207 (3)	0.40086 (13)	0.0346 (4)
H2	0.3036	−0.2017	0.4496	0.042*
C3	0.1433 (2)	−0.2176 (3)	0.35464 (15)	0.0454 (6)
H3	0.0915	−0.3663	0.3727	0.054*
C4	0.0931 (2)	−0.1044 (4)	0.28402 (14)	0.0489 (6)
H4	0.0066	−0.1725	0.2537	0.059*
C5	0.1686 (2)	0.1079 (4)	0.25735 (13)	0.0440 (5)
H5	0.1359	0.1848	0.2075	0.053*
C6	0.2921 (2)	0.2121 (3)	0.30207 (11)	0.0307 (4)
H6	0.3430	0.3614	0.2838	0.037*
C7	0.27851 (18)	0.3331 (3)	0.61695 (10)	0.0197 (4)
C8	0.31935 (19)	0.5376 (3)	0.66473 (9)	0.0244 (4)
H8	0.3868	0.6656	0.6441	0.029*
C9	0.2607 (2)	0.5528 (3)	0.74285 (10)	0.0319 (4)
H9	0.2874	0.6928	0.7765	0.038*
C10	0.1630 (2)	0.3656 (4)	0.77258 (11)	0.0376 (5)
H10	0.1232	0.3763	0.8267	0.045*
C11	0.1238 (2)	0.1643 (3)	0.72383 (12)	0.0360 (5)
H11	0.0562	0.0361	0.7443	0.043*
C12	0.1817 (2)	0.1460 (3)	0.64507 (12)	0.0306 (4)
H12	0.1547	0.0065	0.6113	0.037*
C13A	0.79551 (19)	0.3558 (3)	0.54259 (10)	0.0212 (4)
H13A	0.8017	0.1911	0.5722	0.025*	0.323 (14)
C14A	0.8579 (13)	0.557 (2)	0.6011 (9)	0.042 (3)	0.323 (14)
H14A	0.8401	0.7242	0.5773	0.064*	0.323 (14)
H14B	0.9716	0.5312	0.6104	0.064*	0.323 (14)
H14C	0.8021	0.5444	0.6533	0.064*	0.323 (14)
C15A	0.8791 (19)	0.324 (3)	0.4671 (9)	0.037 (3)	0.323 (14)
H15A	0.8307	0.1869	0.4355	0.056*	0.323 (14)
H15B	0.9902	0.2833	0.4788	0.056*	0.323 (14)
H15C	0.8736	0.4808	0.4354	0.056*	0.323 (14)
C13B	0.79551 (19)	0.3558 (3)	0.54259 (10)	0.0212 (4)	0.00
H13B	0.8085	0.2301	0.5878	0.025*	0.677 (14)
C14B	0.8824 (4)	0.5997 (8)	0.5652 (4)	0.0306 (11)	0.677 (14)
H14D	0.8633	0.7267	0.5227	0.046*	0.677 (14)
H14E	0.9963	0.5662	0.5696	0.046*	0.677 (14)
H14F	0.8434	0.6622	0.6177	0.046*	0.677 (14)
C15B	0.8680 (8)	0.2476 (13)	0.4620 (4)	0.0298 (11)	0.677 (14)
H15D	0.8160	0.0877	0.4482	0.045*	0.677 (14)
H15E	0.9818	0.2188	0.4701	0.045*	0.677 (14)
H15F	0.8517	0.3683	0.4174	0.045*	0.677 (14)

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P1	0.01606 (19)	0.01911 (19)	0.02163 (19)	0.00093 (19)	0.00011 (14)	0.0017 (2)
O1	0.0195 (6)	0.0253 (6)	0.0238 (6)	−0.0048 (5)	−0.0003 (5)	−0.0003 (5)
O2	0.0173 (6)	0.0247 (6)	0.0218 (6)	0.0019 (5)	−0.0019 (4)	0.0017 (5)
O3	0.0239 (6)	0.0191 (6)	0.0313 (6)	0.0014 (4)	0.0029 (5)	0.0024 (5)
N1	0.0184 (7)	0.0154 (7)	0.0265 (8)	0.0024 (5)	−0.0008 (5)	0.0027 (6)
C1	0.0155 (8)	0.0276 (9)	0.0291 (10)	−0.0002 (7)	0.0017 (7)	−0.0118 (7)
C2	0.0318 (11)	0.0258 (9)	0.0462 (12)	−0.0045 (8)	−0.0004 (8)	−0.0038 (9)
C3	0.0349 (12)	0.0286 (11)	0.0727 (17)	−0.0092 (9)	0.0004 (11)	−0.0148 (11)
C4	0.0245 (11)	0.0615 (14)	0.0604 (15)	−0.0062 (10)	−0.0054 (10)	−0.0292 (11)
C5	0.0239 (11)	0.0722 (16)	0.0359 (12)	0.0046 (10)	−0.0064 (8)	−0.0101 (11)
C6	0.0207 (10)	0.0402 (11)	0.0313 (10)	0.0021 (8)	0.0023 (8)	−0.0036 (9)
C7	0.0137 (9)	0.0204 (8)	0.0251 (9)	0.0058 (6)	0.0003 (7)	0.0059 (7)
C8	0.0262 (10)	0.0223 (8)	0.0248 (9)	−0.0025 (7)	−0.0027 (7)	0.0031 (7)
C9	0.0431 (12)	0.0242 (10)	0.0284 (10)	0.0084 (9)	−0.0014 (8)	0.0006 (8)
C10	0.0368 (12)	0.0450 (12)	0.0312 (10)	0.0186 (9)	0.0138 (9)	0.0091 (9)
C11	0.0289 (11)	0.0336 (11)	0.0457 (13)	0.0015 (8)	0.0162 (9)	0.0143 (9)
C12	0.0237 (10)	0.0255 (9)	0.0427 (11)	0.0001 (7)	0.0052 (8)	0.0003 (8)
C13A	0.0166 (9)	0.0217 (8)	0.0253 (9)	0.0034 (6)	−0.0049 (7)	0.0023 (7)
C14A	0.033 (4)	0.043 (4)	0.051 (4)	0.008 (3)	−0.019 (3)	−0.007 (3)
C15A	0.030 (4)	0.038 (5)	0.043 (4)	0.010 (4)	−0.006 (3)	−0.011 (4)
C13B	0.0166 (9)	0.0217 (8)	0.0253 (9)	0.0034 (6)	−0.0049 (7)	0.0023 (7)
C14B	0.0200 (15)	0.0309 (18)	0.041 (2)	0.0000 (12)	−0.0056 (15)	−0.0077 (16)
C15B	0.0230 (18)	0.035 (3)	0.0317 (19)	−0.0010 (19)	0.0069 (14)	−0.007 (2)

P1—O3	1.4602 (11)	C9—C10	1.381 (3)
P1—O1	1.5858 (11)	C9—H9	0.9500
P1—O2	1.5896 (11)	C10—C11	1.371 (3)
P1—N1	1.6043 (14)	C10—H10	0.9500
O1—C1	1.4008 (19)	C11—C12	1.384 (2)
O2—C7	1.4057 (17)	C11—H11	0.9500
N1—C13A	1.4728 (19)	C12—H12	0.9500
N1—H1N	0.811 (13)	C13A—C15A	1.436 (15)
C1—C2	1.373 (2)	C13A—C14A	1.524 (8)
C1—C6	1.378 (2)	C13A—H13A	1.0000
C2—C3	1.393 (3)	C14A—H14A	0.9800
C2—H2	0.9500	C14A—H14B	0.9800
C3—C4	1.366 (3)	C14A—H14C	0.9800
C3—H3	0.9500	C15A—H15A	0.9800
C4—C5	1.367 (3)	C15A—H15B	0.9800
C4—H4	0.9500	C15A—H15C	0.9800
C5—C6	1.383 (3)	C14B—H14D	0.9800
C5—H5	0.9500	C14B—H14E	0.9800
C6—H6	0.9500	C14B—H14F	0.9800
C7—C12	1.367 (2)	C15B—H15D	0.9800
C7—C8	1.379 (2)	C15B—H15E	0.9800
C8—C9	1.376 (2)	C15B—H15F	0.9800
C8—H8	0.9500

O3—P1—O1	114.19 (6)	C12—C7—O2	119.04 (14)
O3—P1—O2	115.82 (6)	C8—C7—O2	118.95 (13)
O1—P1—O2	98.16 (6)	C9—C8—C7	118.79 (15)
O3—P1—N1	114.26 (7)	C9—C8—H8	120.6
O1—P1—N1	106.55 (6)	C7—C8—H8	120.6
O2—P1—N1	106.26 (6)	C8—C9—C10	120.31 (17)
C1—O1—P1	124.07 (10)	C8—C9—H9	119.8
C7—O2—P1	121.74 (10)	C10—C9—H9	119.8
C13A—N1—P1	124.19 (11)	C11—C10—C9	119.82 (16)
C13A—N1—H1N	116.9 (13)	C11—C10—H10	120.1
P1—N1—H1N	117.1 (13)	C9—C10—H10	120.1
C2—C1—C6	121.57 (16)	C10—C11—C12	120.63 (15)
C2—C1—O1	122.74 (15)	C10—C11—H11	119.7
C6—C1—O1	115.65 (14)	C12—C11—H11	119.7
C1—C2—C3	117.70 (19)	C7—C12—C11	118.59 (17)
C1—C2—H2	121.2	C7—C12—H12	120.7
C3—C2—H2	121.2	C11—C12—H12	120.7
C4—C3—C2	121.69 (19)	C15A—C13A—N1	113.1 (7)
C4—C3—H3	119.2	C15A—C13A—C14A	116.8 (6)
C2—C3—H3	119.2	N1—C13A—C14A	105.7 (4)
C3—C4—C5	119.3 (2)	C15A—C13A—H13A	106.9
C3—C4—H4	120.4	N1—C13A—H13A	106.9
C5—C4—H4	120.4	C14A—C13A—H13A	106.9
C4—C5—C6	120.8 (2)	H14D—C14B—H14E	109.5
C4—C5—H5	119.6	H14D—C14B—H14F	109.5
C6—C5—H5	119.6	H14E—C14B—H14F	109.5
C1—C6—C5	118.93 (17)	H15D—C15B—H15E	109.5
C1—C6—H6	120.5	H15D—C15B—H15F	109.5
C5—C6—H6	120.5	H15E—C15B—H15F	109.5
C12—C7—C8	121.86 (15)

O3—P1—O1—C1	67.82 (12)	C2—C1—C6—C5	0.3 (3)
O2—P1—O1—C1	−55.32 (12)	O1—C1—C6—C5	177.98 (15)
N1—P1—O1—C1	−165.06 (11)	C4—C5—C6—C1	1.1 (3)
O3—P1—O2—C7	48.50 (13)	P1—O2—C7—C12	−95.01 (17)
O1—P1—O2—C7	170.46 (11)	P1—O2—C7—C8	89.47 (14)
N1—P1—O2—C7	−79.57 (12)	C12—C7—C8—C9	0.0 (2)
O3—P1—N1—C13A	30.26 (15)	O2—C7—C8—C9	175.40 (15)
O1—P1—N1—C13A	−96.81 (13)	C7—C8—C9—C10	0.2 (3)
O2—P1—N1—C13A	159.24 (12)	C8—C9—C10—C11	−0.4 (3)
P1—O1—C1—C2	−33.7 (2)	C9—C10—C11—C12	0.3 (3)
P1—O1—C1—C6	148.68 (12)	C8—C7—C12—C11	−0.1 (3)
C6—C1—C2—C3	−1.2 (3)	O2—C7—C12—C11	−175.45 (15)
O1—C1—C2—C3	−178.68 (16)	C10—C11—C12—C7	−0.1 (3)
C1—C2—C3—C4	0.7 (3)	P1—N1—C13A—C15A	80.0 (6)
C2—C3—C4—C5	0.7 (3)	P1—N1—C13A—C14A	−150.9 (7)
C3—C4—C5—C6	−1.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3ⁱ	0.81 (1)	2.23 (1)	3.0065 (17)	161 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O3ⁱ	0.81 (1)	2.23 (1)	3.0065 (17)	161 (2)

Symmetry code: (i) .

2 in total

1. A short history of SHELX.

Authors: George M Sheldrick
Journal: Acta Crystallogr A Date: 2007-12-21 Impact factor: 2.290

2. Diphenyl [(S)-1-phenylpropanamido]-phosphate.

Authors: Fahimeh Sabbaghi; Mehrdad Pourayoubi; Monireh Negari; Marek Nečas
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2011-08-27

2 in total