Bis[5-meth-oxy-2-(meth-oxy-carbon-yl)phen-yl] methyl-phospho-nate.

In the title phospho-nate, C19H21O9P, the dihedral angle between the benzene rings is 63.33 (3)°, and the P atom has a distorted tetra-hedral geometry, with angles in the range 101.30 (6)-120.38 (6)°. No significant inter-molecular inter-actions are observed in the crystal structure, and π-π inter-actions between symmetry-related benzene rings are beyond 4 Å.

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 = 424.33

Triclinic,

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[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.102

S = 1.00

5875 reflections

268 parameters

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −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 ▶).

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

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

Click here for additional data file.

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

CCDC reference:

Additional supporting information: crystallographic information; 3D view; checkCIF report

C19H21O9P	Z = 2
Mr = 424.33	F(000) = 444
Triclinic, P1	Dx = 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

Rigaku AFC10/Saturn724+ diffractometer	5875 independent reflections
Radiation source: Rotating Anode	5141 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
Detector resolution: 28.5714 pixels mm-1	θmax = 31.0°, θmin = 2.3°
φ and ω scans	h = −11→11
Absorption correction: multi-scan (CrystalClear; Rigaku, 2008)	k = −15→14
Tmin = 0.890, Tmax = 0.955	l = −17→16
13574 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)] = 0.040	H-atom parameters constrained
wR(F2) = 0.102	w = 1/[σ2(Fo2) + (0.0463P)2 + 0.36P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max = 0.001
5875 reflections	Δρmax = 0.38 e Å−3
268 parameters	Δρmin = −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

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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