[3,3′-Dihy­droxy-3,3′-bis­(pyridin-3-yl-κN)-1,1′-(pyridine-2,6-di­yl)dipropan-1-one](nitrato-κ2O,O′)silver(I)

Dong, J.-Y.; You, T.-P.

doi:10.1107/S1600536811020472

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page m905

doi:10.1107/S1600536811020472

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[3,3′-Dihydroxy-3,3′-bis(pyridin-3-yl-κN)-1,1′-(pyridine-2,6-diyl)dipropan-1-one](nitrato-κ²O,O′)silver(I)

Jian-Yu Dong ^a and Tian-Pa You ^a ^*

^aDepartment of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, People's Republic of China
^*Correspondence e-mail: jianyud@mail.ustc.edu.cn

(Received 25 May 2011; accepted 28 May 2011; online 11 June 2011)

In the title compound, a new macrocyclic metal complex, [Ag(NO₃)(C₂₁H₁₅N₃O₄)], all non-H atoms are in a close-to-planar geometry (except for the nitrate anion), with a maximum out-of-plane deviation of 0.327 (6) Å for a pyridine C atom. The dihedral angle between the least-squares plane through the [3,3′-dihydroxy-3,3′-bis(pyridin-3-yl)-1,1′-(pyridine-2,6-diyl)dipropan-1-one]silver(I) fragment and the nitrate anion is 31.29 (13)°. The molecular structure is stabilized by several inter- and intramolecular O—H⋯O and C—H⋯O hydrogen bonds. The Ag^I atom is coordinated by two pyridine N atoms and two O atoms of the nitrate anion in a geometry intermediate between tetrahedral and square-planar.

Related literature

For general background, see: Zou et al. (2011 ), and references therein. For the synthesis of the ligand, see: Xi et al. (2008 ).

Experimental

Crystal data

[Ag(NO₃)(C₂₁H₁₅N₃O₄)]
M_r = 543.24
Triclinic, $[P \overline 1]$
a = 6.5972 (14) Å
b = 12.572 (3) Å
c = 12.731 (3) Å
α = 101.256 (3)°
β = 101.610 (3)°
γ = 96.454 (3)°
V = 1001.7 (4) Å³
Z = 2
Mo Kα radiation
μ = 1.06 mm⁻¹
T = 298 K
0.33 × 0.27 × 0.19 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.721, T_max = 0.824
5286 measured reflections
3478 independent reflections
2396 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.103
S = 1.06
3478 reflections
298 parameters
H-atom parameters constrained
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.41 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C20—H20⋯O7ⁱ	0.93	2.53	3.386 (6)	154
C12—H12⋯O7ⁱⁱ	0.93	2.51	3.143 (5)	126
C9—H9⋯O6ⁱⁱⁱ	0.93	2.56	3.289 (6)	136
C4—H4A⋯O1^iv	0.93	2.33	3.205 (5)	157
O4—H4⋯O3	0.82	1.85	2.572 (4)	147
O2—H2⋯O1	0.82	1.80	2.531 (4)	147
Symmetry codes: (i) -x+3, -y, -z+1; (ii) -x+3, -y, -z; (iii) x-1, y, z; (iv) -x, -y+1, -z.

Data collection: SMART (Bruker, 2005 ); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811020472/ff2013sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811020472/ff2013Isup2.hkl

checkCIF report

Comment top

The bridging pyridyl compounds are useful ligands to construct metal-cyclic complexes. We here report the synthesis and crystal structure of a novel macrocyclic silver complex containing a bridging pyridyl compound.

The sixteen-component chelate ring is not seen very often. The 16-membered chelate ring composed of atoms Ag1, N2, C9, C10, C8, C7, C6, C5, N1, C1, C14, C15, C6, C18, C17 and N3 has a nearly planar conformation [maximum deviation = 0.117 (5) Å for atom C9]. The molecular structure is stabilized by several intermolecular and intramolecular hydrogen bonds (Table 1).

Bond lengths and angles in the title molecule (Fig. 1) are within normal ranges.

Related literature top

For general background, see: Zou et al. (2011), and references therein. For the synthesis of the ligand, see: Xi et al. (2008).

Experimental top

3,3'-(pyridine-2,6-diyl)bis(1-(pyridin-3-yl)propane-1,3-dione) was synthesized as the reference method (Xi et al., 2008). The title compound was prepared as the following method: 3,3'-(pyridine-2,6-diyl)bis(1-(pyridin-3-yl)propane-1,3-dione) (0.373 g, 1.0 mmol) and AgNO₃ (0.168 g, 1.0 mmol) in 5 ml of DMF were stirred at room temperature for 12 h. The mixture was filtered and afforded the colourless solution. Colourless single crystals suitable for X-ray diffraction were obtained by slow diffusion of diethyl ether into the DMF solution.

Computing details top

Data collection: SMART (Bruker, 2005); cell refinement: SMART (Bruker, 2005); data reduction: SHELXTL (Sheldrick, 2008); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (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 the title compound, showing 30% probability displacement ellipsoids.

[3,3'-Dihydroxy-3,3'-bis(pyridin-3-yl-κN)-1,1'-(pyridine-2,6- diyl)dipropan-1-one](nitrato-κ²O,O')silver(I) top

Crystal data top

[Ag(NO₃)(C₂₁H₁₅N₃O₄)]	Z = 2
M_r = 543.24	F(000) = 544
Triclinic, P1	D_x = 1.801 Mg m⁻³
a = 6.5972 (14) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.572 (3) Å	Cell parameters from 2396 reflections
c = 12.731 (3) Å	θ = 2.1–25°
α = 101.256 (3)°	µ = 1.06 mm⁻¹
β = 101.610 (3)°	T = 298 K
γ = 96.454 (3)°	Block, colourless
V = 1001.7 (4) Å³	0.33 × 0.27 × 0.19 mm

Data collection top

Bruker SMART 1K CCD area-detector diffractometer	3478 independent reflections
Radiation source: fine-focus sealed tube	2396 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→7
T_min = 0.721, T_max = 0.824	k = −14→12
5286 measured reflections	l = −15→14

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.103	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.045P)² + 0.3559P] where P = (F_o² + 2F_c²)/3
3478 reflections	(Δ/σ)_max = 0.001
298 parameters	Δρ_max = 0.49 e Å⁻³
0 restraints	Δρ_min = −0.41 e Å⁻³

Crystal data top

[Ag(NO₃)(C₂₁H₁₅N₃O₄)]	γ = 96.454 (3)°
M_r = 543.24	V = 1001.7 (4) Å³
Triclinic, P1	Z = 2
a = 6.5972 (14) Å	Mo Kα radiation
b = 12.572 (3) Å	µ = 1.06 mm⁻¹
c = 12.731 (3) Å	T = 298 K
α = 101.256 (3)°	0.33 × 0.27 × 0.19 mm
β = 101.610 (3)°

Data collection top

Bruker SMART 1K CCD area-detector diffractometer	3478 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2396 reflections with I > 2σ(I)
T_min = 0.721, T_max = 0.824	R_int = 0.021
5286 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.103	H-atom parameters constrained
S = 1.06	Δρ_max = 0.49 e Å⁻³
3478 reflections	Δρ_min = −0.41 e Å⁻³
298 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
Ag1	1.13449 (6)	0.10254 (4)	0.22826 (3)	0.0692 (2)
N1	0.3450 (5)	0.3863 (3)	0.2614 (3)	0.0450 (9)
N2	0.9937 (5)	0.1445 (3)	0.0679 (3)	0.0488 (9)
N3	1.0707 (5)	0.1360 (3)	0.3959 (3)	0.0521 (10)
N4	1.5330 (6)	0.0178 (3)	0.2232 (3)	0.0557 (10)
O1	0.2448 (5)	0.4261 (3)	−0.0112 (2)	0.0634 (9)
O2	0.4881 (5)	0.3291 (3)	−0.1132 (2)	0.0656 (10)
H2	0.3933	0.3645	−0.1045	0.098*
O3	0.3401 (5)	0.3916 (3)	0.5397 (3)	0.0602 (9)
O4	0.6402 (5)	0.2954 (3)	0.6191 (2)	0.0620 (9)
H4	0.5402	0.3286	0.6193	0.093*
O5	1.4447 (6)	−0.0098 (3)	0.2916 (3)	0.0869 (12)
O6	1.4707 (6)	0.0916 (4)	0.1789 (4)	0.0944 (14)
O7	1.6850 (5)	−0.0217 (3)	0.2017 (3)	0.0801 (11)
C1	0.2705 (7)	0.4022 (4)	0.3526 (4)	0.0477 (11)
C2	0.0891 (7)	0.4478 (4)	0.3574 (4)	0.0577 (13)
H2A	0.0374	0.4561	0.4208	0.069*
C3	−0.0116 (7)	0.4803 (4)	0.2665 (4)	0.0644 (14)
H3	−0.1324	0.5116	0.2683	0.077*
C4	0.0641 (7)	0.4669 (4)	0.1741 (4)	0.0562 (12)
H4A	−0.0014	0.4903	0.1129	0.067*
C5	0.2431 (6)	0.4170 (4)	0.1730 (3)	0.0445 (11)
C6	0.3270 (6)	0.3927 (4)	0.0730 (4)	0.0472 (11)
C7	0.4910 (6)	0.3302 (4)	0.0706 (3)	0.0473 (11)
H7	0.5504	0.3085	0.1341	0.057*
C8	0.5655 (6)	0.3005 (4)	−0.0214 (3)	0.0457 (11)
C9	0.8255 (7)	0.1952 (4)	0.0628 (3)	0.0489 (12)
H9	0.7632	0.2034	0.1226	0.059*
C10	0.7390 (6)	0.2361 (4)	−0.0262 (3)	0.0425 (10)
C11	0.8261 (7)	0.2181 (4)	−0.1166 (4)	0.0581 (13)
H11	0.7708	0.2424	−0.1792	0.070*
C12	0.9963 (8)	0.1633 (4)	−0.1130 (4)	0.0618 (14)
H12	1.0570	0.1503	−0.1733	0.074*
C13	1.0752 (7)	0.1284 (4)	−0.0200 (4)	0.0491 (11)
H13	1.1906	0.0920	−0.0183	0.059*
C14	0.3917 (7)	0.3682 (4)	0.4490 (4)	0.0502 (11)
C15	0.5630 (7)	0.3115 (4)	0.4354 (4)	0.0528 (12)
H15	0.5966	0.2973	0.3670	0.063*
C16	0.6790 (7)	0.2776 (4)	0.5204 (4)	0.0489 (11)
C17	0.9098 (7)	0.1867 (4)	0.4105 (4)	0.0514 (12)
H17	0.8256	0.2017	0.3489	0.062*
C18	0.8581 (7)	0.2187 (4)	0.5100 (3)	0.0472 (11)
C19	0.9853 (8)	0.1955 (5)	0.6011 (4)	0.0709 (16)
H19	0.9584	0.2159	0.6706	0.085*
C20	1.1518 (8)	0.1418 (5)	0.5870 (4)	0.0694 (15)
H20	1.2377	0.1252	0.6471	0.083*
C21	1.1907 (7)	0.1131 (4)	0.4856 (4)	0.0576 (13)
H21	1.3034	0.0765	0.4774	0.069*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ag1	0.0654 (3)	0.1031 (4)	0.0590 (3)	0.0484 (2)	0.02162 (19)	0.0377 (2)
N1	0.041 (2)	0.044 (2)	0.051 (2)	0.0124 (17)	0.0075 (17)	0.0128 (18)
N2	0.048 (2)	0.061 (3)	0.048 (2)	0.0243 (19)	0.0163 (17)	0.0234 (19)
N3	0.044 (2)	0.069 (3)	0.051 (2)	0.018 (2)	0.0092 (17)	0.028 (2)
N4	0.047 (2)	0.065 (3)	0.059 (3)	0.024 (2)	0.0098 (19)	0.019 (2)
O1	0.067 (2)	0.082 (3)	0.054 (2)	0.0439 (19)	0.0091 (16)	0.0328 (18)
O2	0.073 (2)	0.091 (3)	0.0476 (19)	0.046 (2)	0.0133 (16)	0.0331 (18)
O3	0.069 (2)	0.070 (2)	0.0487 (19)	0.0200 (18)	0.0253 (16)	0.0144 (17)
O4	0.065 (2)	0.087 (3)	0.0440 (19)	0.0267 (19)	0.0216 (15)	0.0224 (17)
O5	0.089 (3)	0.103 (3)	0.095 (3)	0.037 (2)	0.047 (2)	0.044 (3)
O6	0.081 (3)	0.125 (4)	0.122 (3)	0.060 (3)	0.048 (2)	0.084 (3)
O7	0.069 (2)	0.112 (3)	0.076 (2)	0.058 (2)	0.0250 (19)	0.026 (2)
C1	0.050 (3)	0.047 (3)	0.047 (3)	0.013 (2)	0.014 (2)	0.008 (2)
C2	0.055 (3)	0.057 (3)	0.062 (3)	0.016 (3)	0.020 (2)	0.005 (3)
C3	0.048 (3)	0.075 (4)	0.071 (3)	0.031 (3)	0.013 (2)	0.009 (3)
C4	0.044 (3)	0.067 (3)	0.061 (3)	0.026 (2)	0.011 (2)	0.016 (3)
C5	0.041 (2)	0.045 (3)	0.048 (3)	0.015 (2)	0.005 (2)	0.014 (2)
C6	0.043 (2)	0.050 (3)	0.052 (3)	0.014 (2)	0.008 (2)	0.020 (2)
C7	0.042 (2)	0.064 (3)	0.042 (2)	0.021 (2)	0.0058 (19)	0.026 (2)
C8	0.045 (2)	0.053 (3)	0.044 (3)	0.017 (2)	0.006 (2)	0.022 (2)
C9	0.053 (3)	0.063 (3)	0.047 (3)	0.031 (2)	0.021 (2)	0.025 (2)
C10	0.042 (2)	0.046 (3)	0.042 (2)	0.011 (2)	0.0092 (19)	0.016 (2)
C11	0.064 (3)	0.078 (4)	0.048 (3)	0.033 (3)	0.019 (2)	0.031 (3)
C12	0.068 (3)	0.083 (4)	0.051 (3)	0.035 (3)	0.029 (2)	0.027 (3)
C13	0.044 (2)	0.061 (3)	0.049 (3)	0.019 (2)	0.016 (2)	0.017 (2)
C14	0.051 (3)	0.048 (3)	0.052 (3)	0.006 (2)	0.013 (2)	0.012 (2)
C15	0.056 (3)	0.069 (3)	0.043 (3)	0.026 (3)	0.015 (2)	0.021 (2)
C16	0.051 (3)	0.054 (3)	0.044 (3)	0.008 (2)	0.014 (2)	0.014 (2)
C17	0.048 (3)	0.065 (3)	0.046 (3)	0.013 (2)	0.005 (2)	0.027 (2)
C18	0.046 (3)	0.060 (3)	0.041 (3)	0.009 (2)	0.009 (2)	0.024 (2)
C19	0.078 (4)	0.104 (5)	0.050 (3)	0.034 (3)	0.020 (3)	0.045 (3)
C20	0.066 (3)	0.098 (4)	0.056 (3)	0.030 (3)	0.006 (3)	0.043 (3)
C21	0.050 (3)	0.065 (3)	0.067 (3)	0.019 (2)	0.010 (2)	0.035 (3)

Geometric parameters (Å, º) top

Ag1—N3	2.228 (4)	C5—N1	1.338 (5)
Ag1—N2	2.253 (3)	C5—C6	1.481 (6)
Ag1—O6	2.435 (4)	C6—O1	1.269 (5)
Ag1—O5	2.695 (4)	C6—C7	1.408 (6)
N1—C1	1.337 (5)	C7—C8	1.362 (6)
N1—C5	1.338 (5)	C7—H7	0.9300
N2—C13	1.326 (5)	C8—C10	1.479 (6)
N2—C9	1.337 (5)	C9—C10	1.380 (5)
N3—C17	1.324 (5)	C9—H9	0.9300
N3—C21	1.352 (5)	C10—C11	1.379 (6)
N4—O5	1.223 (5)	C11—C12	1.379 (6)
N4—O7	1.223 (5)	C11—H11	0.9300
N4—O6	1.242 (5)	C12—C13	1.368 (6)
O1—C6	1.269 (5)	C12—H12	0.9300
O2—C8	1.312 (5)	C13—H13	0.9300
O2—H2	0.8200	C14—O3	1.258 (5)
O3—C14	1.258 (5)	C14—C15	1.424 (6)
O4—C16	1.313 (5)	C15—C16	1.364 (6)
O4—H4	0.8200	C15—H15	0.9300
C1—N1	1.337 (5)	C16—C18	1.478 (6)
C1—C2	1.391 (6)	C17—C18	1.375 (6)
C1—C14	1.489 (6)	C17—H17	0.9300
C2—C3	1.373 (7)	C18—C19	1.390 (6)
C2—H2A	0.9300	C19—C20	1.376 (7)
C3—C4	1.356 (6)	C19—H19	0.9300
C3—H3	0.9300	C20—C21	1.354 (7)
C4—C5	1.399 (6)	C20—H20	0.9300
C4—H4A	0.9300	C21—H21	0.9300

N3—Ag1—N2	134.26 (12)	C6—C7—H7	118.8
N3—Ag1—O6	128.04 (13)	O2—C8—C7	121.5 (4)
N2—Ag1—O6	92.00 (12)	O2—C8—C10	114.8 (4)
N3—Ag1—O5	91.79 (12)	C7—C8—C10	123.6 (4)
N2—Ag1—O5	133.95 (12)	N2—C9—C10	123.8 (4)
O6—Ag1—O5	48.39 (11)	N2—C9—H9	118.1
C1—N1—C5	118.7 (3)	C10—C9—H9	118.1
C13—N2—C9	117.6 (3)	C11—C10—C9	117.4 (4)
C13—N2—Ag1	124.0 (3)	C11—C10—C8	122.0 (4)
C9—N2—Ag1	118.2 (3)	C9—C10—C8	120.6 (4)
C17—N3—C21	117.3 (4)	C10—C11—C12	119.0 (4)
C17—N3—Ag1	117.9 (3)	C10—C11—H11	120.5
C21—N3—Ag1	124.7 (3)	C12—C11—H11	120.5
O5—N4—O7	121.7 (4)	C13—C12—C11	119.4 (4)
O5—N4—O6	118.2 (4)	C13—C12—H12	120.3
O7—N4—O6	120.0 (4)	C11—C12—H12	120.3
C8—O2—H2	109.5	N2—C13—C12	122.6 (4)
C16—O4—H4	109.5	N2—C13—H13	118.7
N4—O5—Ag1	89.7 (3)	C12—C13—H13	118.7
N4—O6—Ag1	101.9 (3)	O3—C14—C15	122.6 (4)
N1—C1—C2	122.0 (4)	O3—C14—C15	122.6 (4)
N1—C1—C2	122.0 (4)	O3—C14—C1	118.7 (4)
N1—C1—C14	116.5 (4)	O3—C14—C1	118.7 (4)
N1—C1—C14	116.5 (4)	C15—C14—C1	118.7 (4)
C2—C1—C14	121.5 (4)	C16—C15—C14	121.4 (4)
C3—C2—C1	118.5 (4)	C16—C15—H15	119.3
C3—C2—H2A	120.8	C14—C15—H15	119.3
C1—C2—H2A	120.8	O4—C16—C15	122.3 (4)
C4—C3—C2	120.3 (4)	O4—C16—C18	114.5 (4)
C4—C3—H3	119.8	C15—C16—C18	123.2 (4)
C2—C3—H3	119.8	N3—C17—C18	124.7 (4)
C3—C4—C5	118.5 (4)	N3—C17—H17	117.6
C3—C4—H4A	120.7	C18—C17—H17	117.6
C5—C4—H4A	120.7	C17—C18—C19	116.9 (4)
N1—C5—C4	121.9 (4)	C17—C18—C16	121.7 (4)
N1—C5—C4	121.9 (4)	C19—C18—C16	121.4 (4)
N1—C5—C6	116.3 (3)	C20—C19—C18	119.0 (5)
N1—C5—C6	116.3 (3)	C20—C19—H19	120.5
C4—C5—C6	121.7 (4)	C18—C19—H19	120.5
O1—C6—C7	120.8 (4)	C21—C20—C19	120.1 (4)
O1—C6—C7	120.8 (4)	C21—C20—H20	120.0
O1—C6—C5	119.1 (4)	C19—C20—H20	120.0
O1—C6—C5	119.1 (4)	N3—C21—C20	122.0 (4)
C7—C6—C5	120.1 (4)	N3—C21—H21	119.0
C8—C7—C6	122.3 (4)	C20—C21—H21	119.0
C8—C7—H7	118.8

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20···O7ⁱ	0.93	2.53	3.386 (6)	154
C12—H12···O7ⁱⁱ	0.93	2.51	3.143 (5)	126
C9—H9···O6ⁱⁱⁱ	0.93	2.56	3.289 (6)	136
C4—H4A···O1^iv	0.93	2.33	3.205 (5)	157
O4—H4···O3	0.82	1.85	2.572 (4)	147
O2—H2···O1	0.82	1.80	2.531 (4)	147

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

Experimental details

Crystal data
Chemical formula	[Ag(NO₃)(C₂₁H₁₅N₃O₄)]
M_r	543.24
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	6.5972 (14), 12.572 (3), 12.731 (3)
α, β, γ (°)	101.256 (3), 101.610 (3), 96.454 (3)
V (Å³)	1001.7 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.06
Crystal size (mm)	0.33 × 0.27 × 0.19

Data collection
Diffractometer	Bruker SMART 1K CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.721, 0.824
No. of measured, independent and observed [I > 2σ(I)] reflections	5286, 3478, 2396
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.103, 1.06
No. of reflections	3478
No. of parameters	298
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.49, −0.41

Computer programs: SMART (Bruker, 2005), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20···O7ⁱ	0.93	2.53	3.386 (6)	153.5
C12—H12···O7ⁱⁱ	0.93	2.51	3.143 (5)	125.9
C9—H9···O6ⁱⁱⁱ	0.93	2.56	3.289 (6)	135.6
C4—H4A···O1^iv	0.93	2.33	3.205 (5)	156.5
O4—H4···O3	0.82	1.85	2.572 (4)	146.9
O2—H2···O1	0.82	1.80	2.531 (4)	147.3

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

Acknowledgements

The authors thank the National Natural Science Foundation of China (grant No. 20872129).

References

Bruker (2005). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Xi, Z. X., Liu, F. H., Zhou, Y. B. & Chen, W. Z. (2008). Tetrahedron, 64, 4254–4259. CrossRef CAS Google Scholar
Zou, P., Liu, Y., Hou, G.-F. & Gao, J.-S. (2011). Acta Cryst. E67, m692. Web of Science CSD CrossRef IUCr Journals Google Scholar

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