Bis(3,5-dimeth­oxy­phen­yl)phosphinic acid

Cheng, W.; Feng, Z.-Q.; Tang, J.-M.

doi:10.1107/S1600536811008440

organic compounds

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ISSN: 2056-9890

Volume 67| Part 4| April 2011| Page o896

doi:10.1107/S1600536811008440

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Bis(3,5-dimethoxyphenyl)phosphinic acid

Wei Cheng,^a ^* Zhi-Qiang Feng ^b and Jun-Mei Tang ^a

^aDepartment of Biological and Chemical Engineering, Chien-Shiung Institute of Technology, Taicang 215411, Suzhou, People's Republic of China, and ^bSchool of Material Engineering, Jinling Institute of Technology, Nanjing 211169, People's Republic of China
^*Correspondence e-mail: larry_18@163.com

(Received 17 February 2011; accepted 6 March 2011; online 15 March 2011)

In the crystal structure of the title compound, C₁₆H₁₉O₆P, intermolecular O—H⋯O interactions link the molecules into chains parallel to the b axis. These chains are linked by C—H⋯π and π–π interactions [centroid–centroid distance = 3.7307 (29) Å] into a three-dimensional network. The dihedral angle between the benzene rings is 73.5 (1)°. The C and O atoms of all four methoxy groups lie very close to the mean planes of their attached rings; the C atoms are 0.055 (2)–0.1038 (1) Å out of the mean plane of the attached rings.

Related literature

For standard bond lengths, see: Allen et al. (1987 ). For the synthesis of the title compound, see: Watson et al. (2006 ).

Experimental

Crystal data

C₁₆H₁₉O₆P
M_r = 338.28
Monoclinic, P 2₁ /n
a = 14.554 (3) Å
b = 7.7620 (16) Å
c = 14.634 (3) Å
β = 96.14 (3)°
V = 1643.7 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 298 K
0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.944, T_max = 0.981
3138 measured reflections
3014 independent reflections
2136 reflections with I > 2σ(I)
R_int = 0.032
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.162
S = 1.01
3014 reflections
208 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C7–C12 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5A⋯O6ⁱ	0.82	1.71	2.482 (3)	155
C14—H14B⋯Cg2ⁱⁱ	0.96	2.90	3.571 (4)	128
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x+2, -y, -z+1.

Data collection: CAD-4 Software (Enraf–Nonius, 1985 ); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811008440/vm2080sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811008440/vm2080Isup2.hkl

checkCIF report

Comment top

The title compound, bis(3,5-dimethoxyphenyl)phosphinic acid (I) is an important intermediate for preparing metal phosphine complexes.

The molecular structure of (I) is shown in Fig. 1. The bond lengths and angles are within normal ranges (Allen et al., 1987).

The dihedral angle between ring 1 (C1—C6) and ring 2 (C7—C12) is 73.5 (1)°. The P atom is situated close to the best planes through the benzene rings (deviation P of -0.054 (1) and 0.014 (1) Å for ring 1 and 2, respectively).

The C and O atoms of all methoxy groups lie very close to the mean planes of their attached rings. The C13 and C14 atoms of methoxy groups are 0.064 (1) and 0.1038 (1) Å, respectively, out of the C1–C6 mean plane. The C15 and C16 atoms are 0.055 (2) and 0.096 (1) Å, respectively, out of the C7–C8 mean plane.

In the crystal structure, intermolecular O—H···O interactions link the molecules into chains parallel to the b-direction (Table 1, Fig. 2). These chains are linked by C—H···π (Table 1) and π—π interactions [distance Cg1···Cg1ⁱⁱ = 3.7307 (29) Å where Cg1 is the centroid of C1—C6; symmetry code ii: 2 - x,-y,1 - z] to give a three-dimensional network, which seems to be very effective in the stabilization of the crystal structure (Fig. 2).

Related literature top

For standard bond lengths, see: Allen et al. (1987). For the synthesis of the title compound, which is commonly used in the preparation of phosphine catalysts, see: Watson et al. (2006).

Experimental top

The title compound was synthesized by the reaction of dimethoxyphenyl bromide, t-BuLi, N,N-dimethylphosphoramic dichloride in aqueous HCl and THF (Watson et al., 2006). Crystals suitable for X-ray analysis were obtained by dissolving the title compound (50 mg) in ethyl acetate (10 ml) and evaporating the solvent slowly at room temperature for about 3 d.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1985); cell refinement: CAD-4 Software (Enraf–Nonius, 1985); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I) with displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. The crystal structure of (I). Dashed lines indicate hydrogen bonds or π—π interactions .

Bis(3,5-dimethoxyphenyl)phosphinic acid top

Crystal data top

C₁₆H₁₉O₆P	F(000) = 712
M_r = 338.28	D_x = 1.367 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 14.554 (3) Å	θ = 10–14°
b = 7.7620 (16) Å	µ = 0.20 mm⁻¹
c = 14.634 (3) Å	T = 298 K
β = 96.14 (3)°	Block, colorless
V = 1643.7 (6) Å³	0.30 × 0.20 × 0.10 mm
Z = 4

Data collection top

Enraf–Nonius CAD-4 diffractometer	2136 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.032
Graphite monochromator	θ_max = 25.4°, θ_min = 1.9°
ω/2θ scans	h = 0→17
Absorption correction: ψ scan (North et al., 1968)	k = 0→9
T_min = 0.944, T_max = 0.981	l = −17→17
3138 measured reflections	3 standard reflections every 200 reflections
3014 independent reflections	intensity decay: 1%

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.162	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.095P)²] where P = (F_o² + 2F_c²)/3
3014 reflections	(Δ/σ)_max < 0.001
208 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

C₁₆H₁₉O₆P	V = 1643.7 (6) Å³
M_r = 338.28	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 14.554 (3) Å	µ = 0.20 mm⁻¹
b = 7.7620 (16) Å	T = 298 K
c = 14.634 (3) Å	0.30 × 0.20 × 0.10 mm
β = 96.14 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	2136 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.032
T_min = 0.944, T_max = 0.981	3 standard reflections every 200 reflections
3138 measured reflections	intensity decay: 1%
3014 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	0 restraints
wR(F²) = 0.162	H-atom parameters constrained
S = 1.01	Δρ_max = 0.26 e Å⁻³
3014 reflections	Δρ_min = −0.32 e Å⁻³
208 parameters

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
P	0.84250 (5)	0.16050 (10)	0.25720 (5)	0.0347 (2)
O1	0.83620 (18)	−0.2020 (3)	0.55369 (14)	0.0568 (7)
C1	0.84208 (19)	−0.0319 (4)	0.41535 (19)	0.0369 (7)
H1A	0.8151	−0.1182	0.3774	0.044*
O2	0.96481 (18)	0.3582 (3)	0.57873 (15)	0.0582 (7)
C2	0.8584 (2)	−0.0570 (4)	0.5091 (2)	0.0388 (7)
O3	0.9727 (2)	−0.3021 (4)	0.0512 (2)	0.0853 (10)
C3	0.8993 (2)	0.0712 (4)	0.5657 (2)	0.0417 (7)
H3A	0.9099	0.0529	0.6287	0.050*
O4	1.17640 (19)	0.1274 (4)	0.1644 (2)	0.0833 (9)
C4	0.9241 (2)	0.2244 (4)	0.5293 (2)	0.0403 (7)
O5	0.85561 (14)	0.3545 (3)	0.23979 (14)	0.0429 (5)
H5A	0.8125	0.4084	0.2577	0.064*
C5	0.9083 (2)	0.2521 (4)	0.4345 (2)	0.0397 (7)
H5B	0.9256	0.3556	0.4093	0.048*
O6	0.74981 (14)	0.0893 (3)	0.22249 (13)	0.0432 (5)
C6	0.86672 (19)	0.1244 (4)	0.37875 (19)	0.0342 (7)
C7	0.9317 (2)	0.0648 (4)	0.19870 (19)	0.0388 (7)
C8	1.0195 (2)	0.1405 (4)	0.2072 (2)	0.0482 (8)
H8A	1.0313	0.2393	0.2424	0.058*
C9	1.0885 (2)	0.0655 (5)	0.1622 (2)	0.0570 (9)
C10	1.0691 (3)	−0.0832 (5)	0.1110 (3)	0.0669 (11)
H10A	1.1156	−0.1346	0.0816	0.080*
C11	0.9820 (3)	−0.1564 (5)	0.1027 (2)	0.0577 (9)
C12	0.9129 (2)	−0.0827 (4)	0.1475 (2)	0.0469 (8)
H12A	0.8544	−0.1320	0.1431	0.056*
C13	0.7992 (3)	−0.3423 (4)	0.5002 (2)	0.0583 (9)
H13A	0.7871	−0.4362	0.5399	0.087*
H13B	0.8426	−0.3782	0.4591	0.087*
H13C	0.7426	−0.3076	0.4653	0.087*
C14	0.9762 (3)	0.3417 (5)	0.6759 (2)	0.0683 (11)
H14A	1.0051	0.4436	0.7026	0.102*
H14B	1.0143	0.2434	0.6929	0.102*
H14C	0.9169	0.3269	0.6979	0.102*
C15	0.8843 (4)	−0.3867 (6)	0.0433 (3)	0.0889 (15)
H15A	0.8867	−0.4879	0.0059	0.133*
H15B	0.8379	−0.3097	0.0154	0.133*
H15C	0.8695	−0.4190	0.1033	0.133*
C16	1.1963 (3)	0.2843 (7)	0.2119 (4)	0.0937 (16)
H16A	1.2597	0.3150	0.2083	0.141*
H16B	1.1859	0.2707	0.2752	0.141*
H16C	1.1569	0.3736	0.1845	0.141*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P	0.0339 (4)	0.0366 (4)	0.0325 (4)	0.0010 (3)	−0.0014 (3)	0.0043 (3)
O1	0.0837 (18)	0.0470 (14)	0.0378 (12)	−0.0164 (12)	−0.0022 (11)	0.0083 (10)
C1	0.0355 (15)	0.0396 (16)	0.0347 (15)	−0.0025 (13)	−0.0010 (12)	−0.0011 (13)
O2	0.0813 (17)	0.0495 (14)	0.0405 (12)	−0.0168 (13)	−0.0085 (11)	−0.0039 (11)
C2	0.0410 (17)	0.0379 (17)	0.0370 (16)	−0.0002 (14)	0.0009 (13)	0.0034 (13)
O3	0.106 (2)	0.0688 (19)	0.088 (2)	−0.0052 (17)	0.0441 (18)	−0.0322 (16)
C3	0.0444 (17)	0.0488 (19)	0.0308 (15)	0.0022 (15)	−0.0016 (13)	0.0010 (14)
O4	0.0547 (16)	0.099 (2)	0.102 (2)	−0.0111 (16)	0.0322 (15)	−0.0187 (19)
C4	0.0409 (17)	0.0399 (17)	0.0384 (16)	−0.0004 (14)	−0.0039 (13)	−0.0040 (14)
O5	0.0405 (12)	0.0402 (12)	0.0480 (12)	0.0013 (10)	0.0044 (9)	0.0060 (10)
C5	0.0435 (17)	0.0362 (17)	0.0386 (16)	−0.0003 (14)	0.0014 (13)	0.0027 (14)
O6	0.0406 (12)	0.0478 (13)	0.0391 (11)	−0.0042 (10)	−0.0060 (9)	0.0079 (10)
C6	0.0290 (15)	0.0383 (16)	0.0345 (15)	0.0030 (12)	−0.0002 (12)	−0.0010 (13)
C7	0.0448 (18)	0.0412 (17)	0.0302 (15)	0.0056 (14)	0.0025 (13)	0.0041 (13)
C8	0.0483 (19)	0.054 (2)	0.0426 (17)	−0.0002 (16)	0.0067 (15)	−0.0035 (15)
C9	0.049 (2)	0.070 (2)	0.055 (2)	0.0012 (18)	0.0166 (16)	0.0011 (19)
C10	0.071 (3)	0.069 (3)	0.066 (2)	0.009 (2)	0.031 (2)	−0.004 (2)
C11	0.079 (3)	0.053 (2)	0.0446 (19)	0.003 (2)	0.0201 (18)	−0.0024 (17)
C12	0.052 (2)	0.0481 (19)	0.0411 (17)	0.0011 (16)	0.0081 (15)	0.0012 (16)
C13	0.077 (3)	0.047 (2)	0.051 (2)	−0.0154 (19)	0.0073 (18)	0.0025 (17)
C14	0.096 (3)	0.066 (3)	0.0411 (19)	−0.021 (2)	−0.0045 (19)	−0.0060 (19)
C15	0.118 (4)	0.065 (3)	0.086 (3)	−0.017 (3)	0.024 (3)	−0.025 (2)
C16	0.062 (3)	0.121 (4)	0.103 (4)	−0.027 (3)	0.030 (3)	−0.020 (3)

Geometric parameters (Å, º) top

P—O6	1.496 (2)	C7—C12	1.379 (4)
P—O5	1.542 (2)	C7—C8	1.400 (4)
P—C7	1.791 (3)	C8—C9	1.387 (5)
P—C6	1.798 (3)	C8—H8A	0.9300
O1—C2	1.357 (4)	C9—C10	1.389 (5)
O1—C13	1.414 (4)	C10—C11	1.383 (5)
C1—C2	1.381 (4)	C10—H10A	0.9300
C1—C6	1.389 (4)	C11—C12	1.381 (5)
C1—H1A	0.9300	C12—H12A	0.9300
O2—C4	1.365 (4)	C13—H13A	0.9600
O2—C14	1.419 (4)	C13—H13B	0.9600
C2—C3	1.388 (4)	C13—H13C	0.9600
O3—C11	1.358 (4)	C14—H14A	0.9600
O3—C15	1.437 (5)	C14—H14B	0.9600
C3—C4	1.367 (4)	C14—H14C	0.9600
C3—H3A	0.9300	C15—H15A	0.9600
O4—C9	1.363 (4)	C15—H15B	0.9600
O4—C16	1.417 (5)	C15—H15C	0.9600
C4—C5	1.397 (4)	C16—H16A	0.9600
O5—H5A	0.8200	C16—H16B	0.9600
C5—C6	1.382 (4)	C16—H16C	0.9600
C5—H5B	0.9300

O6—P—O5	115.32 (12)	O4—C9—C10	116.3 (3)
O6—P—C7	110.96 (14)	C8—C9—C10	119.2 (3)
O5—P—C7	102.55 (13)	C11—C10—C9	121.4 (3)
O6—P—C6	110.65 (13)	C11—C10—H10A	119.3
O5—P—C6	107.51 (13)	C9—C10—H10A	119.3
C7—P—C6	109.45 (13)	O3—C11—C12	125.0 (4)
C2—O1—C13	117.9 (2)	O3—C11—C10	115.3 (3)
C2—C1—C6	118.9 (3)	C12—C11—C10	119.7 (3)
C2—C1—H1A	120.6	C7—C12—C11	119.3 (3)
C6—C1—H1A	120.6	C7—C12—H12A	120.3
C4—O2—C14	117.4 (3)	C11—C12—H12A	120.3
O1—C2—C1	124.8 (3)	O1—C13—H13A	109.5
O1—C2—C3	114.6 (3)	O1—C13—H13B	109.5
C1—C2—C3	120.6 (3)	H13A—C13—H13B	109.5
C11—O3—C15	117.4 (3)	O1—C13—H13C	109.5
C4—C3—C2	120.4 (3)	H13A—C13—H13C	109.5
C4—C3—H3A	119.8	H13B—C13—H13C	109.5
C2—C3—H3A	119.8	O2—C14—H14A	109.5
C9—O4—C16	117.2 (3)	O2—C14—H14B	109.5
O2—C4—C3	124.9 (3)	H14A—C14—H14B	109.5
O2—C4—C5	115.2 (3)	O2—C14—H14C	109.5
C3—C4—C5	119.9 (3)	H14A—C14—H14C	109.5
P—O5—H5A	109.5	H14B—C14—H14C	109.5
C6—C5—C4	119.4 (3)	O3—C15—H15A	109.5
C6—C5—H5B	120.3	O3—C15—H15B	109.5
C4—C5—H5B	120.3	H15A—C15—H15B	109.5
C5—C6—C1	120.9 (3)	O3—C15—H15C	109.5
C5—C6—P	120.0 (2)	H15A—C15—H15C	109.5
C1—C6—P	119.1 (2)	H15B—C15—H15C	109.5
C12—C7—C8	121.5 (3)	O4—C16—H16A	109.5
C12—C7—P	119.5 (2)	O4—C16—H16B	109.5
C8—C7—P	119.0 (2)	H16A—C16—H16B	109.5
C9—C8—C7	118.9 (3)	O4—C16—H16C	109.5
C9—C8—H8A	120.6	H16A—C16—H16C	109.5
C7—C8—H8A	120.6	H16B—C16—H16C	109.5
O4—C9—C8	124.5 (4)

C13—O1—C2—C1	4.3 (5)	O6—P—C7—C12	−14.6 (3)
C13—O1—C2—C3	−176.4 (3)	O5—P—C7—C12	−138.3 (2)
C6—C1—C2—O1	178.8 (3)	C6—P—C7—C12	107.8 (3)
C6—C1—C2—C3	−0.5 (4)	O6—P—C7—C8	166.3 (2)
O1—C2—C3—C4	−179.4 (3)	O5—P—C7—C8	42.6 (3)
C1—C2—C3—C4	0.0 (5)	C6—P—C7—C8	−71.3 (3)
C14—O2—C4—C3	−4.7 (5)	C12—C7—C8—C9	0.6 (5)
C14—O2—C4—C5	175.5 (3)	P—C7—C8—C9	179.7 (2)
C2—C3—C4—O2	−179.9 (3)	C16—O4—C9—C8	−3.7 (6)
C2—C3—C4—C5	−0.1 (5)	C16—O4—C9—C10	176.5 (4)
O2—C4—C5—C6	−179.5 (3)	C7—C8—C9—O4	179.5 (3)
C3—C4—C5—C6	0.7 (5)	C7—C8—C9—C10	−0.7 (5)
C4—C5—C6—C1	−1.2 (4)	O4—C9—C10—C11	−179.1 (4)
C4—C5—C6—P	178.0 (2)	C8—C9—C10—C11	1.0 (6)
C2—C1—C6—C5	1.1 (4)	C15—O3—C11—C12	−0.6 (6)
C2—C1—C6—P	−178.1 (2)	C15—O3—C11—C10	177.8 (4)
O6—P—C6—C5	−139.0 (2)	C9—C10—C11—O3	−179.6 (3)
O5—P—C6—C5	−12.2 (3)	C9—C10—C11—C12	−1.2 (6)
C7—P—C6—C5	98.4 (3)	C8—C7—C12—C11	−0.7 (5)
O6—P—C6—C1	40.2 (3)	P—C7—C12—C11	−179.8 (2)
O5—P—C6—C1	167.0 (2)	O3—C11—C12—C7	179.2 (3)
C7—P—C6—C1	−82.3 (2)	C10—C11—C12—C7	1.0 (5)

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C7–C12 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O6ⁱ	0.82	1.71	2.482 (3)	155
C14—H14B···Cg2ⁱⁱ	0.96	2.90	3.571 (4)	128

Symmetry codes: (i) −x+3/2, y+1/2, −z+1/2; (ii) −x+2, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₉O₆P
M_r	338.28
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	14.554 (3), 7.7620 (16), 14.634 (3)
β (°)	96.14 (3)
V (Å³)	1643.7 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.944, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections	3138, 3014, 2136
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.603

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.162, 1.01
No. of reflections	3014
No. of parameters	208
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.32

Computer programs: CAD-4 Software (Enraf–Nonius, 1985), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C7–C12 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O6ⁱ	0.82	1.71	2.482 (3)	155
C14—H14B···Cg2ⁱⁱ	0.96	2.90	3.571 (4)	128

Symmetry codes: (i) −x+3/2, y+1/2, −z+1/2; (ii) −x+2, −y, −z+1.

Acknowledgements

The authors thank the Center of Testing and Analysis, Nanjing University, for the support.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Enraf–Nonius (1985). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Watson, D. A., Chiu, M. & Bergman, R. G. (2006). Organometallics, 25, 4731–4733. CrossRef PubMed CAS Google Scholar

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Volume 67| Part 4| April 2011| Page o896

doi:10.1107/S1600536811008440

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