Ethyl [1-(4-bromo­phen­yl)-1-hydr­oxy-3-oxobut­yl](phen­yl)phosphinate monohydrate

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

doi:10.1107/S160053681000437X

organic compounds

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ISSN: 2056-9890

Volume 66| Part 3| March 2010| Page o569

doi:10.1107/S160053681000437X

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Ethyl [1-(4-bromophenyl)-1-hydroxy-3-oxobutyl](phenyl)phosphinate monohydrate †

Sampak Samanta,^a Sandun Perera,^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 2 February 2010; accepted 3 February 2010; online 10 February 2010)

In the title hydrate, C₁₈H₂₀BrO₄P·H₂O, a staggered conformation is found when the organic molecule is viewed down the central P—C bond, with the oxo and hydroxyl groups being diagonally opposite; each of the central P and C atoms has an S-configuration. The crystal structure features supramolecular double chains along the b axis mediated by O_hydroxyl–H⋯O_oxo, O_water–H⋯O_oxo, and O_water–H⋯O_water hydrogen bonds.

Related literature

For background to the enantioselective synthesis of the biologically significant R-hydroxyphosphinates, see: Samanta et al. (2010 ).

Experimental

Crystal data

C₁₈H₂₀BrO₄P·H₂O
M_r = 429.24
Monoclinic, P 2₁
a = 10.140 (2) Å
b = 5.7779 (12) Å
c = 16.691 (3) Å
β = 104.79 (3)°
V = 945.5 (3) Å³
Z = 2
Mo Kα radiation
μ = 2.28 mm⁻¹
T = 173 K
0.30 × 0.11 × 0.08 mm

Data collection

Rigaku AFC12/SATURN724 diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.607, T_max = 1
6979 measured reflections
3568 independent reflections
3382 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.094
S = 1.06
3568 reflections
236 parameters
5 restraints
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.37 e Å⁻³
Absolute structure: Flack (1983 ), 1408 Friedel pairs
Flack parameter: 0.015 (10)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1o⋯O2ⁱ	0.84	1.94	2.698 (4)	150
O1w—H1w⋯O2	0.84	2.03	2.855 (4)	168
O1w—H2w⋯O1wⁱⁱ	0.84	2.24	3.072 (6)	172
Symmetry codes: (i) x, y+1, z; (ii) $[-x, y-{\script{1\over 2}}, -z+2]$ .

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: ORTEPII (Johnson, 1976 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681000437X/hb5328sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681000437X/hb5328Isup2.hkl

checkCIF report

Comment top

The title hydrate, (I), was investigated as a part of on-going studies on the enantioselective synthesis of the biologically significant R-hydroxyphosphinates (Samanta et al., 2010). The crystal structure analysis of diastereoisomer in (I), Fig. 1, confirms the stereochemistry of the C1 atom to be S and that of the P2 atom to be likewise S. There are significant hydrogen bonding interactions in the structure and the solvent water molecules play a pivotal role in the supramolecular aggregation. Direct links between molecules are found through the agency of O1_hydroxyl—H1o···O2_oxo hydrogen bonds, Fig. 2 and Table 1. Chains thus formed along the b direction are linked into double chains via a central zig-zag arrangement of hydrogen bonded water molecules that are connected to phosphorous-oxide atoms, Fig. 2 and Table 1. The combination of these O—H···O interactions leads to the formation of 13-membered {···O═ PCOH···O_oxo···HO_waterH···O_waterH···O_waterH} synthons. These chains are connected into layers in the ab plane via C–H···O interactions, Table 1, involving a methyl-H and carbonyl-O atoms, Fig. 3.

Related literature top

For background to the enantioselective synthesis of the biologically significant R-hydroxyphosphinates, see: Samanta et al. (2010).

Experimental top

The title compound was prepared as described in the literature (Samanta et al., 2010). Crystals were obtained by dissolving the diastereomeric products obtained in the cross aldol reaction in a minimum amount of ethyl acetate and then diluting with hexane. The solution was kept in the open to allow solvent slow evaporation, and colourless blocks of (I) were obtained after 24 h.

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: ORTEPII (Johnson, 1976) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: pubCIF (Westrip, 2010).

Figures top

	Fig. 1. Molecular structure of the molecule in (I), showing displacement ellipsoids at the 50% probability level. The water molecule is not shown.
	Fig. 2. Supramolecular double chain along the b axis in (I) mediated by O–H···O hydrogen bonding (orange dashed lines). Colour scheme: Br, olive; P. pink; O, red; N, blue; C, grey; and H, green.
	Fig. 3. View in projection down the b axis of the unit cell contents in (I) highlighting the formation of layers in the ab plane. The O–H···O hydrogen bonding and C–H···O contacts are shown as orange and blue dashed lines, respectively. Colour scheme: Br, olive; P. pink; O, red; N, blue; C, grey; and H, green.

Ethyl [1-(4-bromophenyl)-1-hydroxy-3-oxobutyl](phenyl)phosphinate monohydrate top

Crystal data top

C₁₈H₂₀BrO₄P·H₂O	F(000) = 440
M_r = 429.24	D_x = 1.508 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: P 2yb	Cell parameters from 2824 reflections
a = 10.140 (2) Å	θ = 2.5–30.2°
b = 5.7779 (12) Å	µ = 2.28 mm⁻¹
c = 16.691 (3) Å	T = 173 K
β = 104.79 (3)°	Block, colourless
V = 945.5 (3) Å³	0.30 × 0.11 × 0.08 mm
Z = 2

Data collection top

Rigaku AFC12K/SATURN724 diffractometer	3568 independent reflections
Radiation source: fine-focus sealed tube	3382 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
ω scans	θ_max = 26.5°, θ_min = 2.5°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −12→12
T_min = 0.607, T_max = 1	k = −7→6
6979 measured reflections	l = −20→17

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)] = 0.044	H-atom parameters constrained
wR(F²) = 0.094	w = 1/[σ²(F_o²) + (0.0353P)² + 0.386P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.001
3568 reflections	Δρ_max = 0.31 e Å⁻³
236 parameters	Δρ_min = −0.37 e Å⁻³
5 restraints	Absolute structure: Flack (1983), 1408 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.015 (10)

Crystal data top

C₁₈H₂₀BrO₄P·H₂O	V = 945.5 (3) Å³
M_r = 429.24	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 10.140 (2) Å	µ = 2.28 mm⁻¹
b = 5.7779 (12) Å	T = 173 K
c = 16.691 (3) Å	0.30 × 0.11 × 0.08 mm
β = 104.79 (3)°

Data collection top

Rigaku AFC12K/SATURN724 diffractometer	3568 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	3382 reflections with I > 2σ(I)
T_min = 0.607, T_max = 1	R_int = 0.042
6979 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	H-atom parameters constrained
wR(F²) = 0.094	Δρ_max = 0.31 e Å⁻³
S = 1.06	Δρ_min = −0.37 e Å⁻³
3568 reflections	Absolute structure: Flack (1983), 1408 Friedel pairs
236 parameters	Absolute structure parameter: 0.015 (10)
5 restraints

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
Br14	0.57412 (4)	−0.25929 (15)	0.62623 (3)	0.04821 (16)
P2	0.00084 (10)	0.0452 (2)	0.76819 (6)	0.0228 (2)
O1	0.1397 (3)	0.4301 (5)	0.76143 (18)	0.0293 (6)
H1O	0.0981	0.5136	0.7882	0.044*
O1W	0.0072 (4)	−0.2519 (7)	0.97010 (18)	0.0583 (9)
H1W	0.0023	−0.2549	0.9191	0.087*
H2W	0.0093	−0.3917	0.9841	0.087*
O2	0.0088 (3)	−0.1965 (4)	0.80037 (15)	0.0291 (6)
O3	0.4175 (3)	0.4060 (6)	0.89220 (18)	0.0380 (7)
O21	−0.0871 (2)	0.2144 (5)	0.80840 (14)	0.0259 (5)
C1	0.1642 (3)	0.2055 (7)	0.7962 (2)	0.0220 (8)
C2	0.2089 (4)	0.2109 (7)	0.8912 (2)	0.0276 (8)
H2A	0.1347	0.2829	0.9113	0.033*
H2B	0.2182	0.0491	0.9114	0.033*
C3	0.3397 (4)	0.3364 (6)	0.9309 (2)	0.0283 (9)
C4	0.3666 (5)	0.3686 (9)	1.0232 (3)	0.0445 (12)
H4A	0.3941	0.2205	1.0511	0.067*
H4B	0.2835	0.4240	1.0367	0.067*
H4C	0.4398	0.4822	1.0419	0.067*
C11	0.2671 (4)	0.0904 (6)	0.7559 (2)	0.0228 (8)
C12	0.3013 (4)	0.1955 (7)	0.6892 (2)	0.0309 (9)
H12	0.2608	0.3397	0.6693	0.037*
C13	0.3937 (4)	0.0940 (7)	0.6509 (2)	0.0296 (9)
H13	0.4178	0.1684	0.6059	0.035*
C14	0.4496 (4)	−0.1171 (7)	0.6798 (2)	0.0297 (9)
C15	0.4176 (4)	−0.2265 (7)	0.7454 (2)	0.0299 (9)
H15	0.4573	−0.3718	0.7644	0.036*
C16	0.3267 (4)	−0.1221 (7)	0.7834 (2)	0.0262 (8)
H16	0.3046	−0.1966	0.8290	0.031*
C21	−0.0698 (4)	0.0655 (7)	0.6594 (2)	0.0249 (8)
C22	−0.0543 (4)	−0.1151 (7)	0.6068 (2)	0.0303 (9)
H22	−0.0024	−0.2481	0.6286	0.036*
C23	−0.1158 (4)	−0.0985 (8)	0.5218 (3)	0.0336 (10)
H23	−0.1061	−0.2214	0.4859	0.040*
C24	−0.1898 (4)	0.0934 (7)	0.4901 (3)	0.0367 (10)
H24	−0.2318	0.1019	0.4323	0.044*
C25	−0.2041 (4)	0.2751 (8)	0.5410 (2)	0.0389 (10)
H25	−0.2547	0.4085	0.5182	0.047*
C26	−0.1447 (4)	0.2630 (8)	0.6256 (2)	0.0302 (8)
H26	−0.1547	0.3878	0.6606	0.036*
C31	−0.2290 (4)	0.1602 (8)	0.8061 (3)	0.0384 (10)
H31A	−0.2337	0.0163	0.8375	0.046*
H31B	−0.2827	0.1376	0.7482	0.046*
C32	−0.2844 (5)	0.3569 (9)	0.8440 (3)	0.0504 (13)
H32A	−0.3797	0.3257	0.8431	0.076*
H32B	−0.2792	0.4983	0.8125	0.076*
H32C	−0.2309	0.3771	0.9014	0.076*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br14	0.0388 (2)	0.0579 (3)	0.0544 (3)	0.0052 (2)	0.0236 (2)	−0.0160 (2)
P2	0.0238 (5)	0.0223 (5)	0.0239 (5)	0.0017 (4)	0.0092 (4)	−0.0009 (4)
O1	0.0350 (16)	0.0203 (13)	0.0357 (16)	0.0046 (12)	0.0149 (13)	0.0010 (11)
O1W	0.086 (2)	0.058 (2)	0.0360 (17)	−0.006 (3)	0.0257 (18)	−0.0023 (19)
O2	0.0414 (16)	0.0215 (14)	0.0278 (13)	0.0016 (11)	0.0150 (12)	0.0025 (10)
O3	0.0343 (17)	0.0476 (18)	0.0342 (16)	−0.0089 (14)	0.0123 (14)	−0.0023 (14)
O21	0.0224 (12)	0.0297 (14)	0.0284 (12)	0.0014 (12)	0.0116 (10)	−0.0040 (12)
C1	0.0196 (17)	0.024 (2)	0.0237 (17)	0.0055 (15)	0.0068 (14)	−0.0003 (15)
C2	0.0313 (19)	0.030 (2)	0.0242 (18)	0.0019 (18)	0.0116 (15)	−0.0036 (17)
C3	0.031 (2)	0.0249 (19)	0.029 (2)	0.0062 (16)	0.0062 (17)	0.0001 (16)
C4	0.045 (3)	0.058 (3)	0.030 (2)	−0.009 (2)	0.010 (2)	−0.009 (2)
C11	0.0190 (18)	0.0242 (19)	0.0243 (18)	0.0002 (14)	0.0040 (15)	−0.0031 (15)
C12	0.036 (2)	0.033 (2)	0.0255 (19)	0.0036 (17)	0.0092 (17)	0.0021 (17)
C13	0.034 (2)	0.033 (2)	0.0239 (19)	−0.0012 (17)	0.0110 (17)	−0.0008 (17)
C14	0.023 (2)	0.035 (2)	0.032 (2)	−0.0029 (17)	0.0074 (17)	−0.0130 (18)
C15	0.0232 (19)	0.028 (2)	0.037 (2)	0.0017 (17)	0.0047 (16)	−0.0001 (18)
C16	0.026 (2)	0.0239 (19)	0.0293 (19)	0.0006 (16)	0.0093 (16)	0.0020 (16)
C21	0.0227 (19)	0.0254 (19)	0.0264 (19)	−0.0001 (15)	0.0059 (15)	−0.0036 (15)
C22	0.033 (2)	0.026 (2)	0.031 (2)	0.0067 (17)	0.0069 (18)	−0.0040 (17)
C23	0.039 (2)	0.033 (2)	0.028 (2)	−0.0032 (19)	0.0086 (19)	−0.0100 (17)
C24	0.037 (2)	0.044 (3)	0.027 (2)	0.000 (2)	0.0024 (18)	−0.0053 (19)
C25	0.043 (2)	0.039 (3)	0.031 (2)	0.007 (2)	0.0025 (18)	0.002 (2)
C26	0.036 (2)	0.027 (2)	0.0284 (18)	0.0062 (19)	0.0099 (16)	−0.0020 (18)
C31	0.031 (2)	0.045 (3)	0.044 (2)	−0.0021 (18)	0.018 (2)	−0.0023 (19)
C32	0.037 (3)	0.057 (3)	0.064 (3)	0.017 (2)	0.024 (2)	0.004 (3)

Geometric parameters (Å, º) top

Br14—C14	1.909 (4)	C13—C14	1.379 (6)
P2—O2	1.491 (2)	C13—H13	0.9500
P2—O21	1.584 (3)	C14—C15	1.373 (5)
P2—C21	1.778 (4)	C15—C16	1.383 (5)
P2—C1	1.850 (4)	C15—H15	0.9500
O1—C1	1.418 (5)	C16—H16	0.9500
O1—H1O	0.8400	C21—C22	1.397 (5)
O1W—H1W	0.8400	C21—C26	1.407 (5)
O1W—H2W	0.8400	C22—C23	1.400 (6)
O3—C3	1.209 (5)	C22—H22	0.9500
O21—C31	1.464 (5)	C23—C24	1.368 (6)
C1—C11	1.531 (5)	C23—H23	0.9500
C1—C2	1.534 (4)	C24—C25	1.382 (6)
C2—C3	1.508 (5)	C24—H24	0.9500
C2—H2A	0.9900	C25—C26	1.388 (5)
C2—H2B	0.9900	C25—H25	0.9500
C3—C4	1.506 (5)	C26—H26	0.9500
C4—H4A	0.9800	C31—C32	1.479 (6)
C4—H4B	0.9800	C31—H31A	0.9900
C4—H4C	0.9800	C31—H31B	0.9900
C11—C12	1.388 (5)	C32—H32A	0.9800
C11—C16	1.393 (5)	C32—H32B	0.9800
C12—C13	1.392 (5)	C32—H32C	0.9800
C12—H12	0.9500

O2—P2—O21	114.20 (15)	C13—C14—C15	121.8 (4)
O2—P2—C21	113.59 (17)	C13—C14—Br14	118.6 (3)
O21—P2—C21	105.60 (16)	C15—C14—Br14	119.6 (3)
O2—P2—C1	114.53 (16)	C14—C15—C16	119.0 (4)
O21—P2—C1	98.54 (15)	C14—C15—H15	120.5
C21—P2—C1	109.05 (17)	C16—C15—H15	120.5
C1—O1—H1O	111.5	C15—C16—C11	121.2 (4)
H1W—O1W—H2W	104.7	C15—C16—H16	119.4
C31—O21—P2	120.9 (2)	C11—C16—H16	119.4
O1—C1—C11	106.6 (3)	C22—C21—C26	119.3 (3)
O1—C1—C2	112.3 (3)	C22—C21—P2	120.8 (3)
C11—C1—C2	114.1 (3)	C26—C21—P2	119.9 (3)
O1—C1—P2	107.6 (2)	C21—C22—C23	119.5 (4)
C11—C1—P2	109.7 (2)	C21—C22—H22	120.2
C2—C1—P2	106.3 (2)	C23—C22—H22	120.2
C3—C2—C1	117.3 (3)	C24—C23—C22	120.4 (4)
C3—C2—H2A	108.0	C24—C23—H23	119.8
C1—C2—H2A	108.0	C22—C23—H23	119.8
C3—C2—H2B	108.0	C23—C24—C25	120.7 (4)
C1—C2—H2B	108.0	C23—C24—H24	119.6
H2A—C2—H2B	107.2	C25—C24—H24	119.6
O3—C3—C2	123.1 (3)	C24—C25—C26	120.1 (4)
O3—C3—C4	122.2 (4)	C24—C25—H25	120.0
C2—C3—C4	114.7 (4)	C26—C25—H25	120.0
C3—C4—H4A	109.5	C25—C26—C21	119.9 (4)
C3—C4—H4B	109.5	C25—C26—H26	120.1
H4A—C4—H4B	109.5	C21—C26—H26	120.1
C3—C4—H4C	109.5	O21—C31—C32	107.6 (4)
H4A—C4—H4C	109.5	O21—C31—H31A	110.2
H4B—C4—H4C	109.5	C32—C31—H31A	110.2
C12—C11—C16	118.3 (3)	O21—C31—H31B	110.2
C12—C11—C1	120.0 (3)	C32—C31—H31B	110.2
C16—C11—C1	121.7 (3)	H31A—C31—H31B	108.5
C11—C12—C13	121.3 (4)	C31—C32—H32A	109.5
C11—C12—H12	119.4	C31—C32—H32B	109.5
C13—C12—H12	119.4	H32A—C32—H32B	109.5
C14—C13—C12	118.5 (4)	C31—C32—H32C	109.5
C14—C13—H13	120.8	H32A—C32—H32C	109.5
C12—C13—H13	120.8	H32B—C32—H32C	109.5

O2—P2—O21—C31	−55.9 (3)	C1—C11—C12—C13	−179.5 (3)
C21—P2—O21—C31	69.7 (3)	C11—C12—C13—C14	1.1 (6)
C1—P2—O21—C31	−177.7 (3)	C12—C13—C14—C15	−0.8 (5)
O2—P2—C1—O1	−179.9 (2)	C12—C13—C14—Br14	179.0 (3)
O21—P2—C1—O1	−58.3 (2)	C13—C14—C15—C16	0.1 (6)
C21—P2—C1—O1	51.5 (3)	Br14—C14—C15—C16	−179.7 (3)
O2—P2—C1—C11	64.5 (3)	C14—C15—C16—C11	0.4 (6)
O21—P2—C1—C11	−173.9 (2)	C12—C11—C16—C15	−0.1 (5)
C21—P2—C1—C11	−64.1 (3)	C1—C11—C16—C15	178.8 (3)
O2—P2—C1—C2	−59.4 (3)	O2—P2—C21—C22	−29.9 (4)
O21—P2—C1—C2	62.2 (3)	O21—P2—C21—C22	−155.8 (3)
C21—P2—C1—C2	172.1 (2)	C1—P2—C21—C22	99.1 (3)
O1—C1—C2—C3	−61.6 (4)	O2—P2—C21—C26	148.7 (3)
C11—C1—C2—C3	59.9 (5)	O21—P2—C21—C26	22.8 (4)
P2—C1—C2—C3	−179.0 (3)	C1—P2—C21—C26	−82.3 (3)
C1—C2—C3—O3	−9.4 (6)	C26—C21—C22—C23	−1.3 (6)
C1—C2—C3—C4	170.7 (4)	P2—C21—C22—C23	177.3 (3)
O1—C1—C11—C12	−9.3 (4)	C21—C22—C23—C24	0.5 (6)
C2—C1—C11—C12	−133.8 (4)	C22—C23—C24—C25	0.6 (7)
P2—C1—C11—C12	107.0 (3)	C23—C24—C25—C26	−0.9 (7)
O1—C1—C11—C16	171.9 (3)	C24—C25—C26—C21	0.1 (6)
C2—C1—C11—C16	47.4 (5)	C22—C21—C26—C25	1.0 (6)
P2—C1—C11—C16	−71.8 (4)	P2—C21—C26—C25	−177.6 (3)
C16—C11—C12—C13	−0.7 (5)	P2—O21—C31—C32	−176.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···O2ⁱ	0.84	1.94	2.698 (4)	150
O1w—H1w···O2	0.84	2.03	2.855 (4)	168
O1w—H2w···O1wⁱⁱ	0.84	2.24	3.072 (6)	172

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

Experimental details

Crystal data
Chemical formula	C₁₈H₂₀BrO₄P·H₂O
M_r	429.24
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	173
a, b, c (Å)	10.140 (2), 5.7779 (12), 16.691 (3)
β (°)	104.79 (3)
V (Å³)	945.5 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.28
Crystal size (mm)	0.30 × 0.11 × 0.08

Data collection
Diffractometer	Rigaku AFC12K/SATURN724 diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.607, 1
No. of measured, independent and observed [I > 2σ(I)] reflections	6979, 3568, 3382
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.094, 1.06
No. of reflections	3568
No. of parameters	236
No. of restraints	5
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.37
Absolute structure	Flack (1983), 1408 Friedel pairs
Absolute structure parameter	0.015 (10)

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPII (Johnson, 1976) and DIAMOND (Brandenburg, 2006), pubCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···O2ⁱ	0.84	1.94	2.698 (4)	150
O1w—H1w···O2	0.84	2.03	2.855 (4)	168
O1w—H2w···O1wⁱⁱ	0.84	2.24	3.072 (6)	172

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

Footnotes

†Data reported in this paper were previously deposited with the CCDC (No. 628997).

‡Additional correspondence author: cong.zhao@utsa.edu.

Acknowledgements

The authors thank the NIH-NIGMS (grant No. 1SC1GM082718-01 A1) for financial support of this research and the Welch Foundation (grant No. AX-1593) for financial support for preliminary aspects of this research.

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
Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA. Google Scholar
Rigaku/MSC (2005). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA. Google Scholar
Samanta, S., Perera, S. & Zhao, C.-G. (2010). J. Org. Chem., doi: 10.1021/jo9022099. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). publCIF. In preparation. Google Scholar

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