Bis(propan-2-yl) [(1S)-1-(4-fluoro­phen­yl)-1-hydr­oxy-2-nitro­ethyl]phospho­nate

Mandal, T.; Samanta, S.; Broker, G.A.; Zhao, C.-G.; Tiekink, E.R.T.

doi:10.1107/S160053680905260X

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 1| January 2010| Page o99

doi:10.1107/S160053680905260X

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Bis(propan-2-yl) [(1S)-1-(4-fluorophenyl)-1-hydroxy-2-nitroethyl]phosphonate

Tanmay Mandal,^a Sampak Samanta,^a Grant A. Broker,^a Cong-Gui Zhao ^a ‡ and Edward R. T. Tiekink ^b ^*

^aDepartment of Chemistry, University of Texas at San Antonio, One UTSA Circle, San Antonio, Texas 78249-0698, USA, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 4 December 2009; accepted 7 December 2009; online 12 December 2009)

In the title compound, C₁₄H₂₁FNO₆P, a staggered conformation about the central P—C bond occurs, with the oxo and hydroxyl groups occupying diagonally opposite positions. The crystal structure features supramolecular chains mediated by O—H⋯O hydrogen bonds, which propagate in the a-axis direction. A C—H⋯O interaction consolidates the chains. Disorder was resolved for one of the isopropyl groups with a 0.60 (2):0.40 (2) occupancy ratio for the two components.

Related literature

For background to the enantioselective nitroaldol reaction of α-ketophosphonates and nitromethane and for the synthesis, see: Mandal et al. (2007 ).

Experimental

Crystal data

C₁₄H₂₁FNO₆P
M_r = 349.29
Orthorhombic, P 2₁ 2₁ 2₁
a = 5.8267 (12) Å
b = 15.931 (3) Å
c = 18.273 (4) Å
V = 1696.2 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 173 K
0.31 × 0.15 × 0.06 mm

Data collection

Rigaku AFC12/SATURN724 diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.790, T_max = 1
6049 measured reflections
3391 independent reflections
3248 reflections with I > 2σ(I)
R_int = 0.027
Standard reflections: 0

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.117
S = 1.04
3391 reflections
211 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.43 e Å⁻³
Absolute structure: Flack (1983 ), 1354 Friedel pairs
Flack parameter: −0.11 (13)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4o⋯O1ⁱ	0.84	1.94	2.728 (3)	156
C10—H10⋯O5ⁱⁱ	0.95	2.52	3.447 (4)	164
Symmetry codes: (i) x-1, y, z; (ii) x+1, y, z.

Data collection: CrystalClear (Rigaku/MSC, 2005 ); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680905260X/hb5270sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680905260X/hb5270Isup2.hkl

checkCIF report

Comment top

In connection with previous studies on the enantioselective nitroaldol reaction of α-ketophosphonates and nitromethane for the synthesis of optically active α-hydroxy-β-nitrophosphonates, the title compound, (I), was investigated. The crystal structure analysis of (I), Fig. 1, shows an S-configuration about the C7 atom. When viewed down the P–C7 axis, the molecule has a staggered conformation with the P═O and OH groups being diagonally opposite. The presence of O–H···O hydrogen bonding formed between the hydroxyl-O4—H and O═P atoms leads to the formation of supramolecular chains along [1 0 0], Fig. 2 and Table 1. Stability to these chains of linear topology is afforded by C–H···O contacts, Table 1.

Related literature top

For background to the enantioselective nitroaldol reaction of α-ketophosphonates and nitromethane and for the synthesis, see: Mandal et al. (2007).

Experimental top

The title compound was prepared as described in the literature (Mandal et al., 2007).

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top

	Fig. 1. Molecular structure of (I), showing displacement ellipsoids at the 50% probability level. Only the major component of the C6 position is shown (the atom was refined isotropically).
	Fig. 2. Supramolecular chain along the a axis in (I) mediated by O–H···O (orange dashed lines) hydrogen bonding. Colour scheme: P, pink; F, orange; O, red; N, blue; C, grey; and H, green.

Bis(propan-2-yl) [(1S)-1-(4-fluorophenyl)-1-hydroxy-2-nitroethyl]phosphonate top

Crystal data top

C₁₄H₂₁FNO₆P	F(000) = 736
M_r = 349.29	D_x = 1.368 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 6077 reflections
a = 5.8267 (12) Å	θ = 4.2–30.5°
b = 15.931 (3) Å	µ = 0.20 mm⁻¹
c = 18.273 (4) Å	T = 173 K
V = 1696.2 (6) Å³	Block, colourless
Z = 4	0.31 × 0.15 × 0.06 mm

Data collection top

Rigaku AFC12K/SATURN724 diffractometer	3391 independent reflections
Radiation source: fine-focus sealed tube	3248 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ω scans	θ_max = 26.5°, θ_min = 4.2°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −7→5
T_min = 0.790, T_max = 1	k = −20→13
6049 measured reflections	l = −22→18

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)] = 0.049	H-atom parameters constrained
wR(F²) = 0.117	w = 1/[σ²(F_o²) + (0.0528P)² + 0.8973P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
3391 reflections	Δρ_max = 0.48 e Å⁻³
211 parameters	Δρ_min = −0.43 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1354 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.11 (13)

Crystal data top

C₁₄H₂₁FNO₆P	V = 1696.2 (6) Å³
M_r = 349.29	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 5.8267 (12) Å	µ = 0.20 mm⁻¹
b = 15.931 (3) Å	T = 173 K
c = 18.273 (4) Å	0.31 × 0.15 × 0.06 mm

Data collection top

Rigaku AFC12K/SATURN724 diffractometer	3391 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	3248 reflections with I > 2σ(I)
T_min = 0.790, T_max = 1	R_int = 0.027
6049 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	H-atom parameters constrained
wR(F²) = 0.117	Δρ_max = 0.48 e Å⁻³
S = 1.04	Δρ_min = −0.43 e Å⁻³
3391 reflections	Absolute structure: Flack (1983), 1354 Friedel pairs
211 parameters	Absolute structure parameter: −0.11 (13)
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	Occ. (<1)
P1	0.90429 (11)	0.45039 (4)	0.97285 (3)	0.02753 (16)
F1	1.1808 (4)	0.75747 (13)	0.76550 (11)	0.0698 (7)
O1	1.1339 (3)	0.41823 (11)	0.95590 (10)	0.0332 (4)
O2	0.8946 (3)	0.52834 (11)	1.02505 (10)	0.0351 (4)
O3	0.7358 (3)	0.38649 (12)	1.00898 (10)	0.0367 (5)
O4	0.5136 (3)	0.50239 (11)	0.90853 (11)	0.0321 (4)
H4O	0.4245	0.4648	0.9237	0.048*
O5	0.3934 (4)	0.36867 (16)	0.78091 (14)	0.0629 (7)
O6	0.6260 (6)	0.45661 (17)	0.73135 (13)	0.0832 (10)
N1	0.5743 (5)	0.40835 (15)	0.77945 (14)	0.0468 (6)
C1	1.0726 (5)	0.59419 (18)	1.02606 (16)	0.0428 (7)
H1	1.1352	0.6024	0.9756	0.051*
C2	0.9465 (7)	0.6725 (2)	1.0502 (2)	0.0619 (10)
H2A	0.8252	0.6856	1.0149	0.093*
H2B	1.0545	0.7196	1.0529	0.093*
H2C	0.8782	0.6630	1.0985	0.093*
C3	1.2628 (6)	0.5689 (2)	1.07709 (18)	0.0539 (9)
H3A	1.3373	0.5180	1.0585	0.081*
H3B	1.1992	0.5578	1.1258	0.081*
H3C	1.3758	0.6143	1.0802	0.081*
C4	0.7057 (8)	0.3642 (3)	1.08354 (19)	0.0803 (15)	0.60 (2)
H4	0.6489	0.4155	1.1092	0.096*	0.60 (2)
C5	0.5148 (8)	0.3014 (3)	1.0862 (2)	0.0710 (12)	0.60 (2)
H5A	0.3931	0.3183	1.0522	0.107*	0.60 (2)
H5B	0.4528	0.2987	1.1360	0.107*	0.60 (2)
H5C	0.5735	0.2460	1.0721	0.107*	0.60 (2)
C6	0.9077 (14)	0.3372 (7)	1.1220 (5)	0.058 (2)*	0.60 (2)
H6A	1.0168	0.3839	1.1251	0.087*	0.60 (2)
H6B	0.9786	0.2903	1.0957	0.087*	0.60 (2)
H6C	0.8655	0.3191	1.1715	0.087*	0.60 (2)
C40	0.7057 (8)	0.3642 (3)	1.08354 (19)	0.0803 (15)	0.40 (2)
H40	0.6132	0.4143	1.0983	0.096*	0.40 (2)
C50	0.5148 (8)	0.3014 (3)	1.0862 (2)	0.0710 (12)	0.40 (2)
H50A	0.3931	0.3183	1.0522	0.107*	0.40 (2)
H50B	0.4528	0.2987	1.1360	0.107*	0.40 (2)
H50C	0.5735	0.2460	1.0721	0.107*	0.40 (2)
C60	0.8713 (15)	0.3703 (8)	1.1382 (5)	0.041 (3)*	0.40 (2)
H60A	0.9949	0.4075	1.1218	0.062*	0.40 (2)
H60B	0.9342	0.3145	1.1485	0.062*	0.40 (2)
H60C	0.8014	0.3932	1.1827	0.062*	0.40 (2)
C7	0.7379 (4)	0.47723 (15)	0.88976 (14)	0.0258 (5)
C8	0.7355 (5)	0.39729 (16)	0.84242 (14)	0.0328 (6)
H8A	0.8920	0.3858	0.8239	0.039*
H8B	0.6863	0.3488	0.8725	0.039*
C9	0.8523 (4)	0.55250 (16)	0.85275 (12)	0.0274 (5)
C10	1.0637 (5)	0.54344 (19)	0.81713 (14)	0.0376 (6)
H10	1.1327	0.4896	0.8134	0.045*
C11	1.1721 (5)	0.6126 (2)	0.78744 (17)	0.0464 (8)
H11	1.3149	0.6069	0.7629	0.056*
C12	1.0702 (6)	0.68921 (19)	0.79409 (16)	0.0457 (8)
C13	0.8621 (6)	0.70094 (18)	0.82673 (16)	0.0435 (7)
H13	0.7933	0.7550	0.8285	0.052*
C14	0.7536 (5)	0.63162 (16)	0.85730 (15)	0.0344 (6)
H14	0.6106	0.6385	0.8815	0.041*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P1	0.0271 (3)	0.0296 (3)	0.0259 (3)	−0.0048 (3)	0.0000 (3)	0.0023 (3)
F1	0.0853 (16)	0.0602 (12)	0.0640 (12)	−0.0366 (12)	0.0008 (12)	0.0286 (10)
O1	0.0281 (9)	0.0341 (9)	0.0373 (9)	−0.0007 (8)	−0.0010 (8)	0.0052 (8)
O2	0.0347 (9)	0.0391 (9)	0.0316 (8)	−0.0100 (8)	0.0013 (9)	−0.0067 (8)
O3	0.0377 (10)	0.0416 (10)	0.0307 (9)	−0.0140 (9)	−0.0015 (8)	0.0084 (8)
O4	0.0241 (9)	0.0320 (10)	0.0402 (11)	−0.0023 (8)	0.0052 (8)	0.0023 (9)
O5	0.0469 (13)	0.0661 (15)	0.0756 (16)	0.0048 (13)	−0.0221 (14)	−0.0285 (13)
O6	0.135 (3)	0.0656 (16)	0.0492 (13)	−0.018 (2)	−0.0420 (18)	0.0132 (13)
N1	0.0594 (17)	0.0359 (12)	0.0451 (14)	0.0120 (13)	−0.0185 (14)	−0.0116 (12)
C1	0.0459 (16)	0.0463 (15)	0.0363 (14)	−0.0209 (14)	−0.0003 (15)	−0.0061 (13)
C2	0.076 (3)	0.0427 (17)	0.067 (2)	−0.0038 (18)	−0.015 (2)	−0.0106 (16)
C3	0.0390 (16)	0.076 (2)	0.0469 (17)	−0.0115 (17)	−0.0008 (15)	−0.0171 (17)
C4	0.092 (3)	0.110 (3)	0.0382 (17)	−0.061 (3)	−0.021 (2)	0.032 (2)
C5	0.081 (3)	0.084 (3)	0.0478 (18)	−0.056 (2)	−0.0012 (19)	0.015 (2)
C40	0.092 (3)	0.110 (3)	0.0382 (17)	−0.061 (3)	−0.021 (2)	0.032 (2)
C50	0.081 (3)	0.084 (3)	0.0478 (18)	−0.056 (2)	−0.0012 (19)	0.015 (2)
C7	0.0230 (11)	0.0238 (11)	0.0308 (12)	−0.0007 (9)	0.0024 (10)	−0.0012 (9)
C8	0.0378 (14)	0.0271 (12)	0.0334 (13)	0.0034 (12)	−0.0096 (12)	−0.0024 (10)
C9	0.0310 (13)	0.0290 (12)	0.0223 (10)	−0.0019 (11)	0.0005 (10)	0.0033 (10)
C10	0.0320 (13)	0.0476 (15)	0.0333 (13)	0.0033 (13)	0.0049 (12)	0.0111 (13)
C11	0.0352 (14)	0.062 (2)	0.0421 (15)	−0.0051 (14)	0.0041 (14)	0.0217 (15)
C12	0.0546 (19)	0.0472 (17)	0.0352 (14)	−0.0202 (16)	−0.0075 (15)	0.0172 (13)
C13	0.060 (2)	0.0307 (13)	0.0398 (14)	−0.0088 (14)	−0.0010 (15)	0.0025 (12)
C14	0.0402 (14)	0.0287 (12)	0.0344 (13)	−0.0039 (12)	0.0011 (13)	−0.0005 (11)

Geometric parameters (Å, º) top

P1—O1	1.4656 (19)	C5—H5C	0.9800
P1—O3	1.5609 (19)	C6—H6A	0.9800
P1—O2	1.5670 (19)	C6—H6B	0.9800
P1—C7	1.851 (3)	C6—H6C	0.9800
F1—C12	1.368 (3)	C40—C60	1.392 (9)
O2—C1	1.476 (3)	C40—C50	1.496 (5)
O3—C40	1.419 (4)	C40—H40	1.0000
O3—C4	1.419 (4)	C50—H50A	0.9800
O4—C7	1.409 (3)	C50—H50B	0.9800
O4—H4O	0.8401	C50—H50C	0.9800
O5—N1	1.229 (4)	C60—H60A	0.9800
O6—N1	1.206 (4)	C60—H60B	0.9800
N1—C8	1.496 (4)	C60—H60C	0.9800
C1—C3	1.503 (5)	C7—C9	1.529 (3)
C1—C2	1.514 (5)	C7—C8	1.540 (3)
C1—H1	1.0000	C8—H8A	0.9900
C2—H2A	0.9800	C8—H8B	0.9900
C2—H2B	0.9800	C9—C14	1.388 (4)
C2—H2C	0.9800	C9—C10	1.401 (4)
C3—H3A	0.9800	C10—C11	1.382 (4)
C3—H3B	0.9800	C10—H10	0.9500
C3—H3C	0.9800	C11—C12	1.362 (5)
C4—C6	1.436 (8)	C11—H11	0.9500
C4—C5	1.496 (5)	C12—C13	1.364 (5)
C4—H4	1.0000	C13—C14	1.390 (4)
C5—H5A	0.9800	C13—H13	0.9500
C5—H5B	0.9800	C14—H14	0.9500

O1—P1—O3	115.82 (11)	C60—C40—O3	125.8 (5)
O1—P1—O2	116.03 (11)	C60—C40—C50	122.6 (4)
O3—P1—O2	103.69 (10)	O3—C40—C50	106.9 (3)
O1—P1—C7	112.66 (11)	C60—C40—H40	97.2
O3—P1—C7	99.68 (11)	O3—C40—H40	97.2
O2—P1—C7	107.29 (11)	C50—C40—H40	97.2
C1—O2—P1	123.06 (17)	C40—C50—H50A	109.5
C40—O3—P1	130.3 (2)	C40—C50—H50B	109.5
C4—O3—P1	130.3 (2)	H50A—C50—H50B	109.5
C7—O4—H4O	116.8	C40—C50—H50C	109.5
O6—N1—O5	123.9 (3)	H50A—C50—H50C	109.5
O6—N1—C8	118.6 (3)	H50B—C50—H50C	109.5
O5—N1—C8	117.5 (3)	C40—C60—H60A	109.5
O2—C1—C3	109.6 (2)	C40—C60—H60B	109.5
O2—C1—C2	104.4 (3)	H60A—C60—H60B	109.5
C3—C1—C2	113.5 (3)	C40—C60—H60C	109.5
O2—C1—H1	109.8	H60A—C60—H60C	109.5
C3—C1—H1	109.8	H60B—C60—H60C	109.5
C2—C1—H1	109.8	O4—C7—C9	106.77 (19)
C1—C2—H2A	109.5	O4—C7—C8	111.3 (2)
C1—C2—H2B	109.5	C9—C7—C8	113.8 (2)
H2A—C2—H2B	109.5	O4—C7—P1	110.58 (17)
C1—C2—H2C	109.5	C9—C7—P1	108.40 (16)
H2A—C2—H2C	109.5	C8—C7—P1	105.94 (16)
H2B—C2—H2C	109.5	N1—C8—C7	109.9 (2)
C1—C3—H3A	109.5	N1—C8—H8A	109.7
C1—C3—H3B	109.5	C7—C8—H8A	109.7
H3A—C3—H3B	109.5	N1—C8—H8B	109.7
C1—C3—H3C	109.5	C7—C8—H8B	109.7
H3A—C3—H3C	109.5	H8A—C8—H8B	108.2
H3B—C3—H3C	109.5	C14—C9—C10	119.1 (2)
O3—C4—C6	116.3 (5)	C14—C9—C7	120.3 (2)
O3—C4—C5	106.9 (3)	C10—C9—C7	120.5 (2)
C6—C4—C5	113.2 (4)	C11—C10—C9	120.2 (3)
O3—C4—H4	106.6	C11—C10—H10	119.9
C6—C4—H4	106.6	C9—C10—H10	119.9
C5—C4—H4	106.6	C12—C11—C10	118.7 (3)
C4—C5—H5A	109.5	C12—C11—H11	120.6
C4—C5—H5B	109.5	C10—C11—H11	120.6
H5A—C5—H5B	109.5	C11—C12—C13	123.3 (3)
C4—C5—H5C	109.5	C11—C12—F1	118.2 (3)
H5A—C5—H5C	109.5	C13—C12—F1	118.5 (3)
H5B—C5—H5C	109.5	C12—C13—C14	118.1 (3)
C4—C6—H6A	109.5	C12—C13—H13	120.9
C4—C6—H6B	109.5	C14—C13—H13	120.9
H6A—C6—H6B	109.5	C9—C14—C13	120.6 (3)
C4—C6—H6C	109.5	C9—C14—H14	119.7
H6A—C6—H6C	109.5	C13—C14—H14	119.7
H6B—C6—H6C	109.5

O1—P1—O2—C1	33.2 (2)	O1—P1—C7—C8	55.3 (2)
O3—P1—O2—C1	161.4 (2)	O3—P1—C7—C8	−68.07 (19)
C7—P1—O2—C1	−93.7 (2)	O2—P1—C7—C8	−175.81 (17)
O1—P1—O3—C40	85.5 (4)	O6—N1—C8—C7	69.9 (4)
O2—P1—O3—C40	−42.8 (4)	O5—N1—C8—C7	−108.5 (3)
C7—P1—O3—C40	−153.4 (4)	O4—C7—C8—N1	50.9 (3)
O1—P1—O3—C4	85.5 (4)	C9—C7—C8—N1	−69.8 (3)
O2—P1—O3—C4	−42.8 (4)	P1—C7—C8—N1	171.2 (2)
C7—P1—O3—C4	−153.4 (4)	O4—C7—C9—C14	13.7 (3)
P1—O2—C1—C3	−86.8 (3)	C8—C7—C9—C14	137.0 (2)
P1—O2—C1—C2	151.4 (2)	P1—C7—C9—C14	−105.4 (2)
C40—O3—C4—C6	0 (100)	O4—C7—C9—C10	−169.6 (2)
P1—O3—C4—C6	−54.1 (7)	C8—C7—C9—C10	−46.4 (3)
C40—O3—C4—C5	0 (8)	P1—C7—C9—C10	71.2 (3)
P1—O3—C4—C5	178.4 (3)	C14—C9—C10—C11	0.4 (4)
C4—O3—C40—C60	0 (100)	C7—C9—C10—C11	−176.3 (3)
P1—O3—C40—C60	−25.6 (9)	C9—C10—C11—C12	0.5 (4)
C4—O3—C40—C50	0 (8)	C10—C11—C12—C13	−2.1 (5)
P1—O3—C40—C50	178.4 (3)	C10—C11—C12—F1	179.0 (3)
O1—P1—C7—O4	176.02 (15)	C11—C12—C13—C14	2.7 (5)
O3—P1—C7—O4	52.65 (17)	F1—C12—C13—C14	−178.4 (3)
O2—P1—C7—O4	−55.09 (18)	C10—C9—C14—C13	0.3 (4)
O1—P1—C7—C9	−67.26 (19)	C7—C9—C14—C13	177.0 (2)
O3—P1—C7—C9	169.37 (17)	C12—C13—C14—C9	−1.8 (4)
O2—P1—C7—C9	61.64 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4o···O1ⁱ	0.84	1.94	2.728 (3)	156
C10—H10···O5ⁱⁱ	0.95	2.52	3.447 (4)	164

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

Experimental details

Crystal data
Chemical formula	C₁₄H₂₁FNO₆P
M_r	349.29
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	173
a, b, c (Å)	5.8267 (12), 15.931 (3), 18.273 (4)
V (Å³)	1696.2 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.31 × 0.15 × 0.06

Data collection
Diffractometer	Rigaku AFC12K/SATURN724 diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.790, 1
No. of measured, independent and observed [I > 2σ(I)] reflections	6049, 3391, 3248
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.117, 1.04
No. of reflections	3391
No. of parameters	211
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.48, −0.43
Absolute structure	Flack (1983), 1354 Friedel pairs
Absolute structure parameter	−0.11 (13)

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4o···O1ⁱ	0.84	1.94	2.728 (3)	156
C10—H10···O5ⁱⁱ	0.95	2.52	3.447 (4)	164

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

Footnotes

‡Additional correspondence author, e-mail: cong.zhao@utsa.edu.

Acknowledgements

CGZ thanks the Welch Foundation (grant No. AX-1593) and the NIH-MBRS program (S06 GM08194) for support.

References

Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Mandal, T., Samanta, S. & Zhao, C.-G. (2007). Org. Lett. 9, 943–945. Web of Science CrossRef PubMed CAS Google Scholar
Rigaku/MSC (2005). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2009). publCIF. In preparation. Google Scholar

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Volume 66| Part 1| January 2010| Page o99

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

Bis(propan-2-yl) [(1S)-1-(4-fluoro­phen­yl)-1-hydr­­oxy-2-nitro­ethyl]phospho­nate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

Bis(propan-2-yl) [(1S)-1-(4-fluorophenyl)-1-hydroxy-2-nitroethyl]phosphonate