Bis[5-meth­oxy-2-(meth­oxy­carbon­yl)phen­yl] methyl­phospho­nate

Hussain, S.; Deli, Y.; Parveen, S.; Hao, X.; Zhu, C.

doi:10.1107/S1600536814002542

organic compounds

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ISSN: 2056-9890

Volume 70| Part 3| March 2014| Page o269

doi:10.1107/S1600536814002542

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Bis[5-methoxy-2-(methoxycarbonyl)phenyl] methylphosphonate

Saghir Hussain,^a Yang Deli,^a Shagufta Parveen,^a Xin Hao ^a and Changjin Zhu ^a ^*

^aSchool of Chemical Engineering and Environment, Beijing Institute of Technology, Beijing 100081, People's Republic of China
^*Correspondence e-mail: zcj@bit.edu.cn

(Received 16 December 2013; accepted 4 February 2014; online 12 February 2014)

In the title phosphonate, C₁₉H₂₁O₉P, the dihedral angle between the benzene rings is 63.33 (3)°, and the P atom has a distorted tetrahedral geometry, with angles in the range 101.30 (6)–120.38 (6)°. No significant intermolecular interactions are observed in the crystal structure, and π–π interactions between symmetry-related benzene rings are beyond 4 Å.

CCDC reference: 985024

Related literature

For amidation and esterification of phosphoric acid, see: Kasemsuknimit et al. (2011 ). For the biological activity of phosphonic acids and their ester derivatives, see: Hilderbrand & Henderson (1983 ); Das et al. (2009 ); Wang et al. (2012 ).

Experimental

Crystal data

C₁₉H₂₁O₉P
M_r = 424.33
Triclinic, $[P \overline 1]$
a = 7.852 (2) Å
b = 10.616 (3) Å
c = 12.200 (3) Å
α = 70.774 (9)°
β = 77.800 (9)°
γ = 84.172 (10)°
V = 938.0 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 153 K
0.60 × 0.32 × 0.23 mm

Data collection

Rigaku AFC10/Saturn724+ diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2008 ) T_min = 0.890, T_max = 0.955
13574 measured reflections
5875 independent reflections
5141 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.102
S = 1.00
5875 reflections
268 parameters
H-atom parameters constrained
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.50 e Å⁻³

Data collection: CrystalClear (Rigaku, 2008); 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: CrystalStructure (Rigaku, 2008) and DIAMOND (Brandenburg, 1999 ); software used to prepare material for publication: CrystalStructure (Rigaku, 2008).

Supporting information

CCDC reference: 985024

Crystal structure: contains datablock I. DOI: 10.1107/S1600536814002542/bh2491sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814002542/bh2491Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814002542/bh2491Isup3.cml

checkCIF report

Comment top

Phosphonic acids are very important in understanding and modulating some biological processes (Hilderbrand & Henderson, 1983). For instance, aminophosphonate N-derivatives are potent and selective inhibitors of protein tyrosine phosphatases (Wang et al., 2012). Within this field, phosphonic esters and their derivatives have attracted interest due to their biological activities (Das et al., 2009; Kasemsuknimit et al., 2011). As an extension of these studies, we report herein on the structure of the title compound, C₁₉H₂₁O₉P.

The molecule (Fig. 1) is lying in general position in a triclinic cell. The molecular conformation is centered on a distorted tetrahedral P atom, and benzene rings of oxo substituents make a dihedral angle of 63.33 (3)°. In the crystal structure (Fig. 2), very weak C—H···O intermolecular contacts exist, which involve P═O and C═O groups as acceptors.

Related literature top

For amidation and esterification of phosphoric acid, see: Kasemsuknimit et al. (2011). For the biological activity of phosphonic acids and their ester derivatives, see: Hilderbrand & Henderson (1983); Das et al. (2009); Wang et al. (2012).

Experimental top

A mixture of diethyl methylphosphite (10 mmol) and phosphoryl chloride (10.5 mmol) was refluxed at 55 °C for 48 h. Then, 4-methoxy-methylsalicylate (10 mmol) in CH₂Cl₂ (10 ml) was added dropwise in the presence of triethylamine (4 mmol) to the viscous yellowish reaction mixture and stirred for 30 minutes at 0 °C, and then at room temperature for 48 h. The reaction mixture was extracted with CH₂Cl₂ (3×10 ml) and H₂O (10 ml). The organic layer was washed with 1M HCl (3×10 ml), H₂O (10 ml), dried over MgSO₄, concentrated, and the residue was purified by column chromatography with petroleum ether and ethyl acetate (3:1) as eluent, affording a colorless solid.

Computing details top

Data collection: CrystalClear (Rigaku, 2008); cell refinement: CrystalClear (Rigaku, 2008); data reduction: CrystalClear (Rigaku, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalStructure (Rigaku, 2008) and DIAMOND (Brandenburg, 1999); software used to prepare material for publication: CrystalStructure (Rigaku, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. A view of intermolecular interactions (dotted lines) in the crystal structure of the title compound. H atoms not involved in contacts were omitted for clarity.

Bis[5-methoxy-2-(methoxycarbonyl)phenyl] methylphosphonate top

Crystal data top

C₁₉H₂₁O₉P	Z = 2
M_r = 424.33	F(000) = 444
Triclinic, P1	D_x = 1.502 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.852 (2) Å	Cell parameters from 3814 reflections
b = 10.616 (3) Å	θ = 2.3–31.5°
c = 12.200 (3) Å	µ = 0.20 mm⁻¹
α = 70.774 (9)°	T = 153 K
β = 77.800 (9)°	Prism, colorless
γ = 84.172 (10)°	0.60 × 0.32 × 0.23 mm
V = 938.0 (4) Å³

Data collection top

Rigaku AFC10/Saturn724+ diffractometer	5875 independent reflections
Radiation source: Rotating Anode	5141 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
Detector resolution: 28.5714 pixels mm^-1	θ_max = 31.0°, θ_min = 2.3°
φ and ω scans	h = −11→11
Absorption correction: multi-scan (CrystalClear; Rigaku, 2008)	k = −15→14
T_min = 0.890, T_max = 0.955	l = −17→16
13574 measured reflections

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)] = 0.040	H-atom parameters constrained
wR(F²) = 0.102	w = 1/[σ²(F_o²) + (0.0463P)² + 0.36P] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max = 0.001
5875 reflections	Δρ_max = 0.38 e Å⁻³
268 parameters	Δρ_min = −0.50 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 constraints	Extinction coefficient: 0.018 (2)
Primary atom site location: structure-invariant direct methods

Crystal data top

C₁₉H₂₁O₉P	γ = 84.172 (10)°
M_r = 424.33	V = 938.0 (4) Å³
Triclinic, P1	Z = 2
a = 7.852 (2) Å	Mo Kα radiation
b = 10.616 (3) Å	µ = 0.20 mm⁻¹
c = 12.200 (3) Å	T = 153 K
α = 70.774 (9)°	0.60 × 0.32 × 0.23 mm
β = 77.800 (9)°

Data collection top

Rigaku AFC10/Saturn724+ diffractometer	5875 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2008)	5141 reflections with I > 2σ(I)
T_min = 0.890, T_max = 0.955	R_int = 0.028
13574 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.102	H-atom parameters constrained
S = 1.00	Δρ_max = 0.38 e Å⁻³
5875 reflections	Δρ_min = −0.50 e Å⁻³
268 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
P1	0.33809 (4)	0.27109 (3)	0.77167 (3)	0.01429 (8)
O1	0.32051 (13)	0.73969 (9)	0.92979 (9)	0.0254 (2)
O2	0.05122 (13)	0.15477 (9)	1.15552 (9)	0.0245 (2)
O3	0.29370 (14)	0.10828 (9)	1.03853 (9)	0.0278 (2)
O4	0.42225 (11)	0.33306 (9)	0.85008 (8)	0.01764 (17)
O5	0.40476 (11)	0.36743 (9)	0.64092 (8)	0.01864 (18)
O6	0.14807 (11)	0.26036 (9)	0.80413 (8)	0.01992 (18)
O7	0.12590 (14)	0.79574 (10)	0.48656 (9)	0.0291 (2)
O8	0.33993 (14)	0.27659 (10)	0.35051 (9)	0.0279 (2)
O9	0.32347 (16)	0.17592 (10)	0.54559 (9)	0.0318 (2)
C1	0.33063 (15)	0.40112 (12)	0.92554 (10)	0.0156 (2)
C2	0.36082 (15)	0.53541 (12)	0.89291 (11)	0.0180 (2)
H2	0.4363	0.5776	0.8207	0.022*
C3	0.27920 (15)	0.60907 (12)	0.96717 (11)	0.0177 (2)
C4	0.16437 (16)	0.54847 (12)	1.07129 (11)	0.0183 (2)
H4	0.1058	0.5987	1.1206	0.022*
C5	0.13718 (16)	0.41317 (12)	1.10167 (11)	0.0184 (2)
H5	0.0588	0.3718	1.1728	0.022*
C6	0.22035 (15)	0.33527 (12)	1.03192 (10)	0.0165 (2)
C7	0.24992 (19)	0.81449 (14)	1.00919 (13)	0.0268 (3)
H7A	0.1223	0.8166	1.0222	0.032*
H7B	0.2911	0.9059	0.9747	0.032*
H7C	0.2882	0.7720	1.0848	0.032*
C8	0.19625 (16)	0.18952 (12)	1.07215 (11)	0.0182 (2)
C9	0.0165 (2)	0.01386 (14)	1.19956 (14)	0.0306 (3)
H9A	0.0128	−0.0178	1.1332	0.037*
H9B	−0.0959	−0.0006	1.2544	0.037*
H9C	0.1090	−0.0355	1.2409	0.037*
C10	0.47462 (17)	0.12702 (12)	0.77410 (12)	0.0216 (2)
H10A	0.4780	0.0735	0.8562	0.026*
H10B	0.5927	0.1540	0.7321	0.026*
H10C	0.4286	0.0739	0.7354	0.026*
C11	0.30478 (14)	0.45119 (12)	0.56325 (10)	0.0167 (2)
C12	0.25839 (15)	0.57749 (13)	0.57246 (11)	0.0192 (2)
H12	0.2823	0.6012	0.6361	0.023*
C13	0.17609 (16)	0.66892 (13)	0.48675 (12)	0.0210 (2)
C14	0.14194 (16)	0.63410 (14)	0.39278 (12)	0.0225 (2)
H14	0.0855	0.6965	0.3346	0.027*
C15	0.19083 (16)	0.50850 (13)	0.38535 (11)	0.0215 (2)
H15	0.1691	0.4857	0.3206	0.026*
C16	0.27195 (15)	0.41295 (13)	0.47087 (11)	0.0186 (2)
C17	0.1721 (2)	0.83997 (16)	0.57463 (14)	0.0350 (3)
H17A	0.1159	0.7847	0.6532	0.042*
H17B	0.1331	0.9334	0.5626	0.042*
H17C	0.2989	0.8321	0.5686	0.042*
C18	0.31427 (16)	0.27628 (13)	0.46351 (11)	0.0210 (2)
C19	0.3690 (2)	0.14795 (15)	0.33229 (14)	0.0308 (3)
H19A	0.4530	0.0945	0.3797	0.037*
H19B	0.4152	0.1601	0.2484	0.037*
H19C	0.2586	0.1019	0.3564	0.037*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P1	0.01521 (13)	0.01433 (14)	0.01354 (15)	−0.00011 (10)	−0.00176 (10)	−0.00540 (11)
O1	0.0306 (5)	0.0164 (4)	0.0281 (5)	−0.0045 (4)	0.0032 (4)	−0.0099 (4)
O2	0.0277 (5)	0.0176 (4)	0.0259 (5)	−0.0049 (3)	0.0029 (4)	−0.0075 (4)
O3	0.0359 (5)	0.0169 (4)	0.0263 (5)	0.0033 (4)	0.0007 (4)	−0.0067 (4)
O4	0.0172 (4)	0.0215 (4)	0.0173 (4)	0.0015 (3)	−0.0030 (3)	−0.0111 (3)
O5	0.0155 (4)	0.0235 (4)	0.0140 (4)	0.0004 (3)	−0.0028 (3)	−0.0024 (3)
O6	0.0168 (4)	0.0226 (4)	0.0200 (4)	−0.0034 (3)	−0.0009 (3)	−0.0069 (4)
O7	0.0344 (5)	0.0224 (5)	0.0298 (5)	0.0054 (4)	−0.0085 (4)	−0.0078 (4)
O8	0.0411 (6)	0.0256 (5)	0.0178 (5)	−0.0018 (4)	−0.0029 (4)	−0.0096 (4)
O9	0.0496 (6)	0.0235 (5)	0.0222 (5)	−0.0008 (4)	−0.0092 (5)	−0.0058 (4)
C1	0.0159 (5)	0.0181 (5)	0.0150 (5)	0.0022 (4)	−0.0041 (4)	−0.0081 (4)
C2	0.0190 (5)	0.0185 (5)	0.0167 (5)	−0.0012 (4)	−0.0027 (4)	−0.0061 (4)
C3	0.0197 (5)	0.0149 (5)	0.0195 (6)	−0.0002 (4)	−0.0048 (4)	−0.0063 (4)
C4	0.0212 (5)	0.0177 (5)	0.0175 (6)	0.0014 (4)	−0.0033 (4)	−0.0083 (4)
C5	0.0213 (5)	0.0182 (5)	0.0150 (5)	−0.0001 (4)	−0.0019 (4)	−0.0055 (4)
C6	0.0188 (5)	0.0157 (5)	0.0155 (5)	0.0009 (4)	−0.0042 (4)	−0.0055 (4)
C7	0.0300 (6)	0.0203 (6)	0.0336 (7)	−0.0014 (5)	−0.0027 (6)	−0.0153 (6)
C8	0.0231 (5)	0.0178 (5)	0.0144 (5)	−0.0004 (4)	−0.0051 (4)	−0.0049 (4)
C9	0.0386 (8)	0.0192 (6)	0.0310 (7)	−0.0095 (5)	0.0006 (6)	−0.0059 (5)
C10	0.0265 (6)	0.0170 (5)	0.0211 (6)	0.0040 (4)	−0.0037 (5)	−0.0076 (5)
C11	0.0140 (4)	0.0206 (5)	0.0130 (5)	−0.0015 (4)	−0.0016 (4)	−0.0022 (4)
C12	0.0175 (5)	0.0229 (6)	0.0168 (6)	−0.0021 (4)	−0.0017 (4)	−0.0064 (5)
C13	0.0179 (5)	0.0208 (6)	0.0213 (6)	−0.0007 (4)	−0.0010 (4)	−0.0045 (5)
C14	0.0201 (5)	0.0256 (6)	0.0187 (6)	−0.0006 (5)	−0.0057 (4)	−0.0016 (5)
C15	0.0208 (5)	0.0266 (6)	0.0165 (6)	−0.0038 (5)	−0.0045 (4)	−0.0046 (5)
C16	0.0173 (5)	0.0220 (6)	0.0157 (5)	−0.0030 (4)	−0.0013 (4)	−0.0053 (5)
C17	0.0497 (9)	0.0257 (7)	0.0301 (8)	0.0022 (6)	−0.0056 (7)	−0.0118 (6)
C18	0.0215 (5)	0.0248 (6)	0.0174 (6)	−0.0031 (4)	−0.0023 (4)	−0.0077 (5)
C19	0.0414 (8)	0.0285 (7)	0.0275 (7)	−0.0033 (6)	−0.0056 (6)	−0.0153 (6)

Geometric parameters (Å, º) top

P1—O6	1.4667 (10)	C7—H7A	0.9800
P1—O5	1.5956 (10)	C7—H7B	0.9800
P1—O4	1.5984 (9)	C7—H7C	0.9800
P1—C10	1.7720 (13)	C9—H9A	0.9800
O1—C3	1.3596 (15)	C9—H9B	0.9800
O1—C7	1.4375 (16)	C9—H9C	0.9800
O2—C8	1.3476 (15)	C10—H10A	0.9800
O2—C9	1.4465 (16)	C10—H10B	0.9800
O3—C8	1.2099 (15)	C10—H10C	0.9800
O4—C1	1.3927 (14)	C11—C12	1.3878 (17)
O5—C11	1.3865 (14)	C11—C16	1.3953 (17)
O7—C13	1.3633 (16)	C12—C13	1.3939 (18)
O7—C17	1.4275 (19)	C12—H12	0.9500
O8—C18	1.3494 (16)	C13—C14	1.3971 (19)
O8—C19	1.4428 (17)	C14—C15	1.3764 (19)
O9—C18	1.2063 (17)	C14—H14	0.9500
C1—C2	1.3791 (17)	C15—C16	1.4057 (18)
C1—C6	1.4048 (17)	C15—H15	0.9500
C2—C3	1.4009 (17)	C16—C18	1.4829 (18)
C2—H2	0.9500	C17—H17A	0.9800
C3—C4	1.3914 (17)	C17—H17B	0.9800
C4—C5	1.3872 (17)	C17—H17C	0.9800
C4—H4	0.9500	C19—H19A	0.9800
C5—C6	1.3977 (16)	C19—H19B	0.9800
C5—H5	0.9500	C19—H19C	0.9800
C6—C8	1.4801 (17)

O6—P1—O5	113.96 (5)	O2—C9—H9C	109.5
O6—P1—O4	114.87 (5)	H9A—C9—H9C	109.5
O5—P1—O4	102.31 (5)	H9B—C9—H9C	109.5
O6—P1—C10	120.38 (6)	P1—C10—H10A	109.5
O5—P1—C10	101.53 (6)	P1—C10—H10B	109.5
O4—P1—C10	101.30 (6)	H10A—C10—H10B	109.5
C3—O1—C7	116.45 (10)	P1—C10—H10C	109.5
C8—O2—C9	115.46 (10)	H10A—C10—H10C	109.5
C1—O4—P1	125.45 (8)	H10B—C10—H10C	109.5
C11—O5—P1	127.58 (8)	O5—C11—C12	117.91 (11)
C13—O7—C17	117.67 (11)	O5—C11—C16	119.54 (11)
C18—O8—C19	116.33 (11)	C12—C11—C16	122.11 (11)
C2—C1—O4	116.28 (10)	C11—C12—C13	118.90 (12)
C2—C1—C6	121.84 (11)	C11—C12—H12	120.6
O4—C1—C6	121.81 (11)	C13—C12—H12	120.6
C1—C2—C3	119.46 (11)	O7—C13—C12	123.89 (12)
C1—C2—H2	120.3	O7—C13—C14	115.62 (12)
C3—C2—H2	120.3	C12—C13—C14	120.48 (12)
O1—C3—C4	124.13 (11)	C15—C14—C13	119.34 (12)
O1—C3—C2	115.46 (11)	C15—C14—H14	120.3
C4—C3—C2	120.41 (11)	C13—C14—H14	120.3
C5—C4—C3	118.65 (11)	C14—C15—C16	121.86 (12)
C5—C4—H4	120.7	C14—C15—H15	119.1
C3—C4—H4	120.7	C16—C15—H15	119.1
C4—C5—C6	122.68 (11)	C11—C16—C15	117.30 (12)
C4—C5—H5	118.7	C11—C16—C18	122.28 (11)
C6—C5—H5	118.7	C15—C16—C18	120.39 (11)
C5—C6—C1	116.89 (11)	O7—C17—H17A	109.5
C5—C6—C8	120.60 (11)	O7—C17—H17B	109.5
C1—C6—C8	122.47 (10)	H17A—C17—H17B	109.5
O1—C7—H7A	109.5	O7—C17—H17C	109.5
O1—C7—H7B	109.5	H17A—C17—H17C	109.5
H7A—C7—H7B	109.5	H17B—C17—H17C	109.5
O1—C7—H7C	109.5	O9—C18—O8	122.93 (12)
H7A—C7—H7C	109.5	O9—C18—C16	126.15 (12)
H7B—C7—H7C	109.5	O8—C18—C16	110.91 (11)
O3—C8—O2	122.46 (12)	O8—C19—H19A	109.5
O3—C8—C6	125.90 (12)	O8—C19—H19B	109.5
O2—C8—C6	111.62 (10)	H19A—C19—H19B	109.5
O2—C9—H9A	109.5	O8—C19—H19C	109.5
O2—C9—H9B	109.5	H19A—C19—H19C	109.5
H9A—C9—H9B	109.5	H19B—C19—H19C	109.5

O6—P1—O4—C1	−14.43 (11)	C1—C6—C8—O3	19.6 (2)
O5—P1—O4—C1	109.57 (10)	C5—C6—C8—O2	20.16 (16)
C10—P1—O4—C1	−145.81 (10)	C1—C6—C8—O2	−162.06 (11)
O6—P1—O5—C11	8.28 (12)	P1—O5—C11—C12	85.25 (13)
O4—P1—O5—C11	−116.33 (10)	P1—O5—C11—C16	−102.25 (12)
C10—P1—O5—C11	139.24 (10)	O5—C11—C12—C13	172.42 (10)
P1—O4—C1—C2	−112.42 (11)	C16—C11—C12—C13	0.12 (18)
P1—O4—C1—C6	70.66 (14)	C17—O7—C13—C12	4.73 (19)
O4—C1—C2—C3	−177.17 (10)	C17—O7—C13—C14	−174.46 (12)
C6—C1—C2—C3	−0.26 (18)	C11—C12—C13—O7	−179.55 (11)
C7—O1—C3—C4	5.11 (18)	C11—C12—C13—C14	−0.39 (18)
C7—O1—C3—C2	−174.95 (11)	O7—C13—C14—C15	179.04 (11)
C1—C2—C3—O1	178.09 (11)	C12—C13—C14—C15	−0.18 (19)
C1—C2—C3—C4	−1.97 (18)	C13—C14—C15—C16	1.06 (19)
O1—C3—C4—C5	−177.96 (12)	O5—C11—C16—C15	−171.47 (10)
C2—C3—C4—C5	2.11 (18)	C12—C11—C16—C15	0.71 (17)
C3—C4—C5—C6	−0.03 (19)	O5—C11—C16—C18	10.56 (17)
C4—C5—C6—C1	−2.08 (18)	C12—C11—C16—C18	−177.27 (11)
C4—C5—C6—C8	175.82 (11)	C14—C15—C16—C11	−1.30 (18)
C2—C1—C6—C5	2.22 (17)	C14—C15—C16—C18	176.71 (12)
O4—C1—C6—C5	178.97 (10)	C19—O8—C18—O9	3.7 (2)
C2—C1—C6—C8	−175.63 (11)	C19—O8—C18—C16	−175.42 (11)
O4—C1—C6—C8	1.11 (17)	C11—C16—C18—O9	26.3 (2)
C9—O2—C8—O3	−1.95 (18)	C15—C16—C18—O9	−151.63 (14)
C9—O2—C8—C6	179.59 (11)	C11—C16—C18—O8	−154.61 (11)
C5—C6—C8—O3	−158.23 (13)	C15—C16—C18—O8	27.48 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7B···O3ⁱ	0.98	2.52	3.3134 (18)	138
C9—H9A···O6ⁱⁱ	0.98	2.79	3.3198 (18)	115

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

Experimental details

Crystal data
Chemical formula	C₁₉H₂₁O₉P
M_r	424.33
Crystal system, space group	Triclinic, P1
Temperature (K)	153
a, b, c (Å)	7.852 (2), 10.616 (3), 12.200 (3)
α, β, γ (°)	70.774 (9), 77.800 (9), 84.172 (10)
V (Å³)	938.0 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.60 × 0.32 × 0.23

Data collection
Diffractometer	Rigaku AFC10/Saturn724+ diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2008)
T_min, T_max	0.890, 0.955
No. of measured, independent and observed [I > 2σ(I)] reflections	13574, 5875, 5141
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.725

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.102, 1.00
No. of reflections	5875
No. of parameters	268
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.50

Computer programs: CrystalClear (Rigaku, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), CrystalStructure (Rigaku, 2008) and DIAMOND (Brandenburg, 1999), CrystalStructure (Rigaku, 2008).

Acknowledgements

This work was supported by the National Natural Science Foundation of China (grant No. 21272025), the Research Fund for the Doctoral Program of Higher Education of China (grant No. 20111101110042) and the Science and Technology Commission of Beijing (China) (grant No. Z131100004013003).

References

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