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Acta Cryst. (2007). E63, m2338    [ doi:10.1107/S1600536807038846 ]

A two-dimensional holmium(III) coordination polymer: poly[aminotris([mu]-4-aminobenzoato)holmium(III)]

Y.-L. Feng, J.-S. Xu, D.-Z. Kuang and Y.-L. Peng

Abstract top

In the title compound, [Ho(C7H6NO2)3(H2O)]n, a two-dimensional coordination polymer, the eight-coordinate HoIII ions are bridged by two carboxylate groups from two 4-aminobenzoate ligands, forming a centrosymmetric dinuclear block. These blocks are further connected by 4-aminobenzoate ligands, yielding a two-dimensional network; a three-dimensional supramolecular structure is then formed via hydrogen bonds.

Comment top

During the last two decades, lanthanide complexes have received much attention because of their interesting photophysical properties which have potential applications in the luminescent probes for chemical or biological macromolecules and the active center for luminescent materials(Chu et al., 2001; Kepert & Rosseinsky, 1998; Reineke et al., 1999; Chen et al., 2006;). We have chosen 4-aminobenzonitrile as ligand and investigated its reaction with Ho2O3 under hydrothermal synthesis, and report herein the X-ray crystal structure of the novel terbium coordination polymer, [Ho(4-aminobenzoate)3(H2O)]n, (I).

In (I) (Fig. 1), the HoIII center is eight-coordinated by six O atoms from five different 4-aminobenzoate ligands, one N atoms from a 4-aminobenzoate ligand and one O atoms from a coordinated water molecule, thus the HoIII ion has a distorted bicapped trigonal prism. In the coordination polyhedron of HoIII ion, the Ho—O distance of carboxyl is in the range 2.337 (2)–2.482 (2) Å, and the mean Ho—O bond length is 2.428 (2) Å. The Ho—O bond length involving the coordination water is 2.546 (2) Å, and the Ho—N distance is 2.691 (3) Å. In (I), each 4-aminobenzoate ligand adopts an O,O-bidentate bridging mode using a carboxylate group. Adjacent HoIII centers are doubly bridged by the ligands, forming a big eight-membered ring, while the other two Ho atoms has a 16-membered ring bridged by the carboxylate groups and amino groups (Fig. 2).

Related literature top

For related literature, see: Chen et al. (2006); Chu et al. (2001); Kepert & Rosseinsky (1998); Reineke et al. (1999).

Experimental top

A mixture of Ho2O3 (0.25 mmol), 4-aminobenzonitrile (2.0 mmol), H2O (10 ml, 0.55 mmol) and two drops of acetic acid with the pH value of about 3.0, was heated in a 25 ml capacity Teflon-lined reaction vessel at 160 ° for 5 days, the reaction mixture was cooled to room temperature over a period of 48 h. The product was collected by filtration, washed with H2O and air-dried, colorless crystals suitable for X-ray analysis were obtained. Analysis calculated (%): C, 42.62; H, 3.38; N, 7.10%; Found: C, 43.05; H, 3.32%; N, 7.17%.

Refinement top

H atoms bonded to C atoms were placed geometrically and treated as riding, (C—H distances are 0.93 Å), with Uiso(H) = 1.2Ueq(C). The water H atoms found from Fourier difference maps were refined with restraints for O—H distances (0.816–0.817 Å) and Uiso(H) fixed at 0.05.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 2003); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The ORTEP drawing of the title compound (I). Displacement ellipsoids are drawn at 30% probability level. The symmetry codes are: A: −x + 1,-y + 1,-z + 2 B: −x + 1,-y + 1,-z + 1 C: −x,-y + 1,-z + 1
[Figure 2] Fig. 2. Projection showing the two-dimensional layer structure of the compound (I).
poly[aminotris(µ-4-aminobenzoato)holmium(III)] top
Crystal data top
[Ho(C7H6NO2)3(H2O)]F000 = 1160
Mr = 591.33Dx = 1.824 Mg m−3
Monoclinic, P21/nMo Kα radiation
λ = 0.71073 Å
a = 9.772 (1) ÅCell parameters from 30 reflections
b = 22.761 (3) Åθ = 4.9–13.5º
c = 9.832 (1) ŵ = 3.72 mm−1
β = 100.02 (1)ºT = 294 (2) K
V = 2153.5 (4) Å3Block, colorless
Z = 40.24 × 0.20 × 0.18 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer		4001 independent reflections
Radiation source: fine-focus sealed tube2954 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.014
T = 294(2) Kθmax = 25.5º
φ and ω scansθmin = 1.8º
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)		h = 0→11
Tmin = 0.413, Tmax = 0.512k = 0→27
4521 measured reflectionsl = −11→11
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.021H atoms treated by a mixture of
independent and constrained refinement
wR(F2) = 0.052  w = 1/[σ2(Fo2) + (0.027P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
4005 reflectionsΔρmax = 0.44 e Å−3
322 parametersΔρmin = −0.53 e Å−3
10 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods
Crystal data top
[Ho(C7H6NO2)3(H2O)]V = 2153.5 (4) Å3
Mr = 591.33Z = 4
Monoclinic, P21/nMo Kα
a = 9.772 (1) ŵ = 3.72 mm−1
b = 22.761 (3) ÅT = 294 (2) K
c = 9.832 (1) Å0.24 × 0.20 × 0.18 mm
β = 100.02 (1)º
Data collection top
Bruker SMART CCD area-detector
diffractometer		4001 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)		2954 reflections with I > 2σ(I)
Tmin = 0.413, Tmax = 0.512Rint = 0.014
4521 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.02110 restraints
wR(F2) = 0.052H atoms treated by a mixture of
independent and constrained refinement
S = 1.03Δρmax = 0.44 e Å−3
4005 reflectionsΔρmin = −0.53 e Å−3
322 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
xyzUiso*/Ueq
Ho0.481566 (14)0.501123 (7)0.758702 (13)0.01914 (7)
O10.3005 (2)0.52755 (10)0.5758 (2)0.0273 (5)
O20.3446 (2)0.48881 (9)0.3815 (2)0.0288 (6)
O30.3698 (3)0.54166 (10)0.9282 (2)0.0334 (6)
O40.3944 (3)0.58076 (11)1.1353 (2)0.0371 (6)
O50.5125 (2)0.60754 (10)0.7181 (2)0.0288 (5)
O60.6608 (2)0.56728 (9)0.8857 (2)0.0272 (5)
N1−0.2838 (3)0.57271 (13)0.1850 (3)0.0245 (6)
N20.1092 (4)0.79410 (17)0.7699 (5)0.0550 (10)
N30.8320 (4)0.83857 (14)0.9754 (3)0.0373 (8)
C10.0375 (3)0.56663 (14)0.4452 (3)0.0253 (7)
H10.06870.57910.53540.030*
C2−0.0937 (3)0.58147 (13)0.3808 (3)0.0258 (7)
H2−0.14930.60490.42630.031*
C3−0.1444 (3)0.56162 (14)0.2473 (3)0.0242 (7)
C4−0.0586 (3)0.52806 (16)0.1795 (3)0.0317 (8)
H4−0.09110.51480.09030.038*
C50.0748 (4)0.51421 (14)0.2436 (3)0.0306 (8)
H50.13180.49200.19710.037*
C60.1244 (3)0.53352 (14)0.3786 (3)0.0219 (7)
C70.2652 (3)0.51582 (12)0.4497 (3)0.0217 (7)
C80.2766 (4)0.68773 (15)1.0271 (4)0.0343 (8)
H80.31350.68671.12090.041*
C90.2192 (4)0.73920 (16)0.9689 (4)0.0401 (9)
H90.21850.77251.02370.048*
C100.1626 (4)0.74188 (15)0.8301 (4)0.0370 (9)
C110.1606 (4)0.69082 (16)0.7522 (4)0.0381 (9)
H110.11840.69120.65990.046*
C120.2196 (4)0.64017 (15)0.8089 (3)0.0339 (8)
H120.21930.60690.75380.041*
C130.2802 (3)0.63734 (14)0.9478 (3)0.0259 (7)
C140.3513 (3)0.58321 (14)1.0068 (3)0.0254 (7)
C150.8018 (4)0.67744 (15)0.9384 (3)0.0319 (8)
H150.85480.64420.96570.038*
C160.8547 (4)0.73237 (15)0.9764 (4)0.0348 (8)
H160.94330.73581.02860.042*
C170.7770 (4)0.78271 (14)0.9375 (3)0.0303 (8)
C180.6457 (4)0.77666 (15)0.8593 (4)0.0384 (9)
H180.59220.80980.83260.046*
C190.5935 (4)0.72156 (15)0.8207 (4)0.0342 (8)
H190.50530.71820.76760.041*
C200.6701 (4)0.67137 (14)0.8595 (3)0.0269 (7)
C210.6117 (3)0.61238 (14)0.8182 (3)0.0257 (7)
O70.4542 (3)0.41368 (11)0.5947 (2)0.0293 (5)
H1A−0.292 (4)0.5723 (15)0.0963 (11)0.035 (10)*
H1B−0.311 (3)0.6058 (8)0.210 (3)0.034 (10)*
H2A0.067 (3)0.8143 (14)0.822 (3)0.042 (12)*
H2B0.062 (4)0.792 (2)0.689 (2)0.12 (3)*
H3A0.888 (3)0.8377 (15)1.0532 (19)0.035 (11)*
H3B0.768 (3)0.8636 (14)0.981 (3)0.054 (14)*
H7A0.520 (3)0.3920 (16)0.590 (5)0.075 (17)*
H7B0.427 (4)0.4282 (16)0.519 (2)0.051 (13)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ho0.01833 (9)0.01936 (9)0.01852 (9)0.00174 (9)−0.00016 (5)−0.00054 (8)
O10.0259 (12)0.0290 (12)0.0234 (12)0.0024 (10)−0.0058 (10)−0.0016 (10)
O20.0213 (11)0.0363 (15)0.0289 (11)0.0033 (10)0.0044 (10)−0.0005 (10)
O30.0408 (15)0.0235 (12)0.0386 (14)0.0086 (11)0.0142 (12)0.0004 (11)
O40.0403 (15)0.0374 (15)0.0291 (13)0.0108 (12)−0.0063 (12)0.0032 (11)
O50.0308 (13)0.0235 (12)0.0274 (12)−0.0008 (10)−0.0082 (11)−0.0003 (10)
O60.0312 (13)0.0218 (12)0.0255 (12)0.0006 (10)−0.0039 (10)0.0026 (10)
N10.0188 (14)0.0298 (16)0.0235 (15)0.0026 (12)−0.0002 (12)−0.0014 (13)
N20.062 (3)0.038 (2)0.066 (3)0.0252 (19)0.013 (2)0.0180 (19)
N30.041 (2)0.0280 (17)0.042 (2)−0.0095 (15)0.0051 (16)−0.0054 (14)
C10.0233 (17)0.0300 (18)0.0205 (15)−0.0028 (14)−0.0013 (13)−0.0046 (14)
C20.0230 (17)0.0264 (17)0.0276 (17)0.0012 (14)0.0036 (14)−0.0059 (14)
C30.0189 (16)0.0293 (17)0.0231 (16)0.0003 (14)0.0002 (13)0.0047 (13)
C40.0234 (18)0.048 (2)0.0216 (16)0.0016 (17)−0.0027 (14)−0.0081 (16)
C50.0239 (17)0.044 (2)0.0245 (17)0.0034 (15)0.0051 (13)−0.0073 (14)
C60.0180 (16)0.0244 (17)0.0220 (16)0.0001 (13)−0.0001 (13)0.0035 (13)
C70.0189 (16)0.0184 (17)0.0272 (16)−0.0038 (12)0.0024 (14)0.0018 (12)
C80.032 (2)0.036 (2)0.0332 (19)0.0071 (17)0.0021 (16)−0.0032 (16)
C90.045 (2)0.0256 (19)0.049 (2)0.0056 (17)0.0083 (19)−0.0072 (17)
C100.034 (2)0.0284 (19)0.051 (2)0.0120 (16)0.0146 (18)0.0098 (17)
C110.044 (2)0.042 (2)0.0256 (18)0.0127 (18)−0.0008 (16)0.0069 (16)
C120.041 (2)0.0314 (19)0.0285 (18)0.0109 (17)0.0032 (16)−0.0027 (15)
C130.0273 (18)0.0241 (17)0.0261 (17)0.0083 (14)0.0046 (14)0.0022 (14)
C140.0210 (17)0.0245 (17)0.0312 (19)0.0039 (14)0.0061 (14)0.0043 (14)
C150.0280 (19)0.0264 (18)0.039 (2)−0.0015 (15)−0.0017 (16)0.0009 (16)
C160.0270 (19)0.036 (2)0.039 (2)−0.0074 (16)−0.0015 (16)−0.0034 (17)
C170.037 (2)0.0258 (18)0.0297 (18)−0.0115 (15)0.0109 (16)−0.0017 (14)
C180.043 (2)0.0220 (18)0.047 (2)0.0039 (16)0.0012 (19)−0.0002 (16)
C190.030 (2)0.030 (2)0.038 (2)0.0000 (15)−0.0069 (16)−0.0002 (16)
C200.0326 (19)0.0226 (17)0.0241 (17)−0.0065 (14)0.0013 (15)−0.0010 (13)
C210.0265 (18)0.0251 (18)0.0253 (17)−0.0017 (14)0.0038 (15)−0.0057 (14)
O70.0325 (15)0.0290 (14)0.0265 (13)0.0058 (11)0.0053 (11)0.0007 (11)
Geometric parameters (Å, °) top
Ho—O32.337 (2)C3—C41.388 (4)
Ho—O4i2.364 (2)C4—C51.382 (5)
Ho—O12.371 (2)C4—H40.9300
Ho—O2ii2.379 (2)C5—C61.403 (4)
Ho—O62.478 (2)C5—H50.9300
Ho—O52.482 (2)C6—C71.487 (4)
Ho—O72.546 (2)C8—C91.380 (5)
Ho—N1iii2.691 (3)C8—C131.391 (5)
O1—C71.257 (4)C8—H80.9300
O2—C71.270 (4)C9—C101.382 (5)
O2—Hoii2.379 (2)C9—H90.9300
O3—C141.254 (4)C10—C111.390 (5)
O4—C141.263 (4)C11—C121.364 (5)
O4—Hoi2.364 (2)C11—H110.9300
O5—C211.262 (4)C12—C131.393 (4)
O6—C211.270 (4)C12—H120.9300
N1—C31.417 (4)C13—C141.482 (4)
N1—Hoiii2.691 (3)C15—C161.379 (4)
N1—H1A0.861 (10)C15—C201.390 (5)
N1—H1B0.850 (10)C15—H150.9300
N2—C101.389 (5)C16—C171.392 (5)
N2—H2A0.849 (10)C16—H160.9300
N2—H2B0.851 (10)C17—C181.384 (5)
N3—C171.405 (4)C18—C191.382 (5)
N3—H3A0.858 (10)C18—H180.9300
N3—H3B0.856 (10)C19—C201.383 (5)
C1—C21.371 (4)C19—H190.9300
C1—C61.383 (4)C20—C211.488 (4)
C1—H10.9300O7—H7A0.817 (10)
C2—C31.395 (4)O7—H7B0.816 (10)
C2—H20.9300
O3—Ho—O4i105.32 (8)C2—C3—N1120.5 (3)
O3—Ho—O193.52 (8)C5—C4—C3120.5 (3)
O4i—Ho—O1142.40 (8)C5—C4—H4119.8
O3—Ho—O2ii147.74 (8)C3—C4—H4119.8
O4i—Ho—O2ii88.18 (8)C4—C5—C6120.2 (3)
O1—Ho—O2ii92.87 (8)C4—C5—H5119.9
O3—Ho—O677.16 (8)C6—C5—H5119.9
O4i—Ho—O689.61 (8)C1—C6—C5118.7 (3)
O1—Ho—O6126.70 (7)C1—C6—C7121.3 (3)
O2ii—Ho—O673.72 (7)C5—C6—C7120.0 (3)
O3—Ho—O579.32 (8)O1—C7—O2122.4 (3)
O4i—Ho—O5140.61 (8)O1—C7—C6118.7 (3)
O1—Ho—O574.09 (7)O2—C7—C6118.9 (3)
O2ii—Ho—O572.15 (8)C9—C8—C13121.0 (3)
O6—Ho—O552.62 (7)C9—C8—H8119.5
O3—Ho—O7138.60 (8)C13—C8—H8119.5
O4i—Ho—O769.67 (8)C8—C9—C10120.8 (3)
O1—Ho—O774.66 (8)C8—C9—H9119.6
O2ii—Ho—O773.43 (8)C10—C9—H9119.6
O6—Ho—O7141.40 (8)C9—C10—N2121.0 (4)
O5—Ho—O7131.53 (7)C9—C10—C11118.2 (3)
O3—Ho—N1iii69.98 (8)N2—C10—C11120.8 (4)
O4i—Ho—N1iii75.45 (9)C12—C11—C10121.1 (3)
O1—Ho—N1iii81.16 (8)C12—C11—H11119.4
O2ii—Ho—N1iii142.27 (8)C10—C11—H11119.4
O6—Ho—N1iii138.27 (8)C11—C12—C13121.2 (3)
O5—Ho—N1iii138.98 (8)C11—C12—H12119.4
O7—Ho—N1iii69.05 (8)C13—C12—H12119.4
O3—Ho—C2175.52 (9)C8—C13—C12117.6 (3)
O4i—Ho—C21115.69 (9)C8—C13—C14121.5 (3)
O1—Ho—C21100.27 (9)C12—C13—C14120.8 (3)
O2ii—Ho—C2172.24 (8)O3—C14—O4121.7 (3)
O6—Ho—C2126.44 (8)O3—C14—C13119.6 (3)
O5—Ho—C2126.24 (8)O4—C14—C13118.7 (3)
O7—Ho—C21144.97 (9)C16—C15—C20120.6 (3)
N1iii—Ho—C21145.48 (9)C16—C15—H15119.7
C7—O1—Ho137.4 (2)C20—C15—H15119.7
C7—O2—Hoii145.5 (2)C15—C16—C17120.7 (3)
C14—O3—Ho150.8 (2)C15—C16—H16119.6
C14—O4—Hoi122.2 (2)C17—C16—H16119.6
C21—O5—Ho93.32 (19)C18—C17—C16118.7 (3)
C21—O6—Ho93.30 (18)C18—C17—N3120.9 (3)
C3—N1—Hoiii118.1 (2)C16—C17—N3120.4 (3)
C3—N1—H1A111 (2)C19—C18—C17120.4 (3)
Hoiii—N1—H1A105 (2)C19—C18—H18119.8
C3—N1—H1B111 (2)C17—C18—H18119.8
Hoiii—N1—H1B103 (2)C18—C19—C20121.2 (3)
H1A—N1—H1B109 (3)C18—C19—H19119.4
C10—N2—H2A113 (3)C20—C19—H19119.4
C10—N2—H2B117 (4)C19—C20—C15118.5 (3)
H2A—N2—H2B111.4 (18)C19—C20—C21120.4 (3)
C17—N3—H3A112 (2)C15—C20—C21121.1 (3)
C17—N3—H3B112 (3)O5—C21—O6120.5 (3)
H3A—N3—H3B108.6 (16)O5—C21—C20119.9 (3)
C2—C1—C6121.2 (3)O6—C21—C20119.6 (3)
C2—C1—H1119.4O5—C21—Ho60.44 (16)
C6—C1—H1119.4O6—C21—Ho60.26 (16)
C1—C2—C3120.4 (3)C20—C21—Ho174.2 (2)
C1—C2—H2119.8Ho—O7—H7A120 (3)
C3—C2—H2119.8Ho—O7—H7B104 (3)
C4—C3—C2119.0 (3)H7A—O7—H7B110 (4)
C4—C3—N1120.4 (3)
O3—Ho—O1—C7−167.7 (3)C13—C8—C9—C100.5 (6)
O4i—Ho—O1—C7−46.8 (4)C8—C9—C10—N2−177.6 (4)
O2ii—Ho—O1—C744.0 (3)C8—C9—C10—C112.3 (6)
O6—Ho—O1—C7115.8 (3)C9—C10—C11—C12−3.5 (6)
O5—Ho—O1—C7114.5 (3)N2—C10—C11—C12176.4 (4)
O7—Ho—O1—C7−28.0 (3)C10—C11—C12—C131.9 (6)
N1iii—Ho—O1—C7−98.6 (3)C9—C8—C13—C12−2.2 (6)
C21—Ho—O1—C7116.4 (3)C9—C8—C13—C14175.2 (3)
O4i—Ho—O3—C14116.5 (5)C11—C12—C13—C81.0 (6)
O1—Ho—O3—C14−96.4 (5)C11—C12—C13—C14−176.4 (3)
O2ii—Ho—O3—C144.7 (5)Ho—O3—C14—O4−107.2 (5)
O6—Ho—O3—C1430.5 (5)Ho—O3—C14—C1371.2 (6)
O5—Ho—O3—C14−23.3 (4)Hoi—O4—C14—O31.3 (4)
O7—Ho—O3—C14−167.0 (4)Hoi—O4—C14—C13−177.1 (2)
N1iii—Ho—O3—C14−175.6 (5)C8—C13—C14—O3−169.8 (3)
C21—Ho—O3—C143.3 (4)C12—C13—C14—O37.5 (5)
O3—Ho—O5—C2178.9 (2)C8—C13—C14—O48.7 (5)
O4i—Ho—O5—C21−22.3 (2)C12—C13—C14—O4−174.1 (3)
O1—Ho—O5—C21175.7 (2)C20—C15—C16—C170.4 (5)
O2ii—Ho—O5—C21−85.9 (2)C15—C16—C17—C18−0.3 (5)
O6—Ho—O5—C21−3.06 (18)C15—C16—C17—N3−179.3 (3)
O7—Ho—O5—C21−132.63 (19)C16—C17—C18—C19−0.1 (5)
N1iii—Ho—O5—C21120.5 (2)N3—C17—C18—C19178.9 (3)
O3—Ho—O6—C21−83.24 (19)C17—C18—C19—C200.4 (6)
O4i—Ho—O6—C21170.95 (19)C18—C19—C20—C15−0.3 (5)
O1—Ho—O6—C211.5 (2)C18—C19—C20—C21179.4 (3)
O2ii—Ho—O6—C2182.74 (19)C16—C15—C20—C19−0.1 (5)
O5—Ho—O6—C213.04 (18)C16—C15—C20—C21−179.8 (3)
O7—Ho—O6—C21115.4 (2)Ho—O5—C21—O65.5 (3)
N1iii—Ho—O6—C21−121.70 (19)Ho—O5—C21—C20−173.3 (3)
C6—C1—C2—C32.2 (5)Ho—O6—C21—O5−5.5 (3)
C1—C2—C3—C4−1.8 (5)Ho—O6—C21—C20173.3 (3)
C1—C2—C3—N1174.7 (3)C19—C20—C21—O520.0 (5)
Hoiii—N1—C3—C492.5 (3)C15—C20—C21—O5−160.3 (3)
Hoiii—N1—C3—C2−83.9 (3)C19—C20—C21—O6−158.8 (3)
C2—C3—C4—C50.4 (5)C15—C20—C21—O620.8 (5)
N1—C3—C4—C5−176.1 (3)O3—Ho—C21—O5−95.2 (2)
C3—C4—C5—C60.6 (5)O4i—Ho—C21—O5164.48 (17)
C2—C1—C6—C5−1.2 (5)O1—Ho—C21—O5−4.2 (2)
C2—C1—C6—C7−178.1 (3)O2ii—Ho—C21—O585.51 (19)
C4—C5—C6—C1−0.2 (5)O6—Ho—C21—O5174.5 (3)
C4—C5—C6—C7176.7 (3)O7—Ho—C21—O573.7 (2)
Ho—O1—C7—O2−11.6 (5)N1iii—Ho—C21—O5−93.5 (2)
Ho—O1—C7—C6167.5 (2)O3—Ho—C21—O690.23 (19)
Hoii—O2—C7—O1−91.0 (4)O4i—Ho—C21—O6−10.1 (2)
Hoii—O2—C7—C689.9 (4)O1—Ho—C21—O6−178.77 (18)
C1—C6—C7—O15.5 (4)O2ii—Ho—C21—O6−89.03 (19)
C5—C6—C7—O1−171.3 (3)O5—Ho—C21—O6−174.5 (3)
C1—C6—C7—O2−175.3 (3)O7—Ho—C21—O6−100.9 (2)
C5—C6—C7—O27.8 (4)N1iii—Ho—C21—O691.9 (2)
Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) −x+1, −y+1, −z+1; (iii) −x, −y+1, −z+1.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O6iv0.861 (10)2.046 (12)2.902 (3)172 (3)
N1—H1B···N2v0.850 (10)2.510 (11)3.360 (5)177 (3)
N2—H2A···O7vi0.849 (10)2.43 (3)3.139 (5)142 (3)
N3—H3A···O5vii0.858 (10)2.23 (2)2.974 (4)145 (3)
O7—H7B···O20.816 (10)2.000 (18)2.773 (3)158 (4)
O7—H7A···N3viii0.817 (10)2.079 (16)2.875 (4)165 (5)
Symmetry codes: (iv) x−1, y, z−1; (v) x−1/2, −y+3/2, z−1/2; (vi) −x+1/2, y+1/2, −z+3/2; (vii) x+1/2, −y+3/2, z+1/2; (viii) −x+3/2, y−1/2, −z+3/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O6i0.861 (10)2.046 (12)2.902 (3)172 (3)
N1—H1B···N2ii0.850 (10)2.510 (11)3.360 (5)177 (3)
N2—H2A···O7iii0.849 (10)2.43 (3)3.139 (5)142 (3)
N3—H3A···O5iv0.858 (10)2.23 (2)2.974 (4)145 (3)
O7—H7B···O20.816 (10)2.000 (18)2.773 (3)158 (4)
O7—H7A···N3v0.817 (10)2.079 (16)2.875 (4)165 (5)
Symmetry codes: (i) x−1, y, z−1; (ii) x−1/2, −y+3/2, z−1/2; (iii) −x+1/2, y+1/2, −z+3/2; (iv) x+1/2, −y+3/2, z+1/2; (v) −x+3/2, y−1/2, −z+3/2.
Acknowledgements top

This work was supported by the Foundation of the Eleventh Five-Year Key Constructing Discipline of Hunan Province and Hunan Provincial Natural Science Foundation of China (grant No. 06 J J2015).

references
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