metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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{μ-6,6′-Dimeth­­oxy-2,2′-[butane-1,4-diylbis(nitrilo­methanylyl­­idene)]diphenolato}trinitratocopper(II)samarium(III)

aDepartment of Anesthesiology, the Second Affiliated Hospital, Harbin Medical University, Harbin 150081, People's Republic of China
*Correspondence e-mail: xiaoguangcui008@yahoo.cn

(Received 6 July 2011; accepted 2 August 2011; online 6 August 2011)

In the monomeric dinuclear title complex, [CuSm(C20H22N2O4)(NO3)3], the four-coordinate CuII ion has a square-planar geometry involving two O atoms and two N atoms of the deprotonated Schiff base ligand. The SmIII ion is ten-coordinate, chelated by four O donor atoms of the Schiff base and two O atoms each from three bidentate nitrate groups, one of which is disordered over two sites in a 0.55 (7):0.45 (7) ratio.

Related literature

For copper–lanthanide complexes of the same or similar Schiff bases, see: Xing et al. (2009[Xing, J.-C., Xu, Y.-M., Cui, X.-G. & Li, W.-Z. (2009). Acta Cryst. E65, m443.], 2010[Xing, J.-C., Cui, X.-G., Zhang, B. & Li, W.-Z. (2010). Acta Cryst. E66, m1423.]).

[Scheme 1]

Experimental

Crystal data
  • [CuSm(C20H22N2O4)(NO3)3]

  • Mr = 754.32

  • Monoclinic, P 21 /n

  • a = 11.764 (2) Å

  • b = 14.786 (3) Å

  • c = 15.004 (3) Å

  • β = 100.73 (3)°

  • V = 2564.3 (9) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 3.17 mm−1

  • T = 295 K

  • 0.24 × 0.18 × 0.15 mm

Data collection
  • Rigaku R-AXIS RAPID CCD diffractometer

  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995[Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.516, Tmax = 0.648

  • 24339 measured reflections

  • 5855 independent reflections

  • 5046 reflections with I > 2σ(I)

  • Rint = 0.037

Refinement
  • R[F2 > 2σ(F2)] = 0.026

  • wR(F2) = 0.062

  • S = 1.04

  • 5855 reflections

  • 373 parameters

  • H-atom parameters constrained

  • Δρmax = 0.77 e Å−3

  • Δρmin = −0.38 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998[Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.]); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002[Rigaku/MSC (2002). CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

In the monomeric dinuclear title complex, [CuSm(C20H22N2O4)(NO3)3], (Fig. 1) the four-coordinate CuII ion has square-planar geometry involving two O atoms and two N atoms of the deprotonated Schiff base. The SmIII ion is ten-coordinate, chelated by four O donor atoms of the Schiff base and three bidentate nitrato groups, one of which is disordered over two sites (S.O.F. 0.55/0.45). This complex is isomorphous with the CuII–NdIII complex with the same ligand (Xing et al., 2010) and has similar features to those reported for the CuII–LuIII complex with a similar ligand (Xing et al., 2009)

Related literature top

For copper–lanthanide complexes of the same or similar Schiff bases, see: Xing et al. (2009, 2010).

Experimental top

The title complex was obtained by the reaction of copper(II) acetate monohydrate (0.0499 g, 0.25 mmol) with the Schiff base (0.1595 g, 0.25 mmol) in methanol/acetone (20 ml:5 ml) at room temperature. The mixture was then refluxed for 3 h after the addition of samarium(III) nitrate hexahydrate (0.1143 g, 0.25 mmol). The reaction mixture was cooled and filtered and diethyl ether was allowed to diffuse slowly into the solution. Single crystals were obtained after several days. Analysis: calculated for C20H22CuN5O13Sm: C, 31.82; H, 2.92; Cu, 8.42; N, 9.28; Sm, 19.93%. Found: C, 32.80; H, 2.94; Cu, 8.45; N, 9.29; Sm, 19.91%.

Refinement top

H atoms bound to C were placed in calculated positions and treated as riding on their parent atoms, with C—H = 0.93 Å (aromatic), C—H = 0.97 Å (methylene), and with Uiso(H) = 1.2Ueq(C) or C—H = 0.96 Å (methyl) and with Uiso(H) = 1.5Ueq(C). One of the nitrate groups incorporating N5 is disordered over two sites, with occupancies of 0.55 (7) and 0.45 (7).

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); 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
[Figure 1] Fig. 1. The molecular structure and atom numbering scheme for the title complex, showing 40% probability displacement ellipsoids. All H atoms have been omitted for clarity.
{µ-6,6'-Dimethoxy-2,2'-[butane-1,4- diylbis(nitrilomethanylylidene)]diphenolato}trinitratocopper(II)samarium(III) top
Crystal data top
[CuSm(C20H22N2O4)(NO3)3]F(000) = 1488
Mr = 754.32Dx = 1.954 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 19348 reflections
a = 11.764 (2) Åθ = 3.1–27.4°
b = 14.786 (3) ŵ = 3.17 mm1
c = 15.004 (3) ÅT = 295 K
β = 100.73 (3)°Prism, brown
V = 2564.3 (9) Å30.24 × 0.18 × 0.15 mm
Z = 4
Data collection top
Rigaku R-AXIS RAPID CCD
diffractometer
5855 independent reflections
Radiation source: fine-focus sealed tube5046 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.037
Detector resolution: 10.00 pixels mm-1θmax = 27.5°, θmin = 3.1°
ω scansh = 1315
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
k = 1919
Tmin = 0.516, Tmax = 0.648l = 1919
24339 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.026Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.062H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0242P)2 + 1.6986P]
where P = (Fo2 + 2Fc2)/3
5855 reflections(Δ/σ)max = 0.001
373 parametersΔρmax = 0.77 e Å3
0 restraintsΔρmin = 0.38 e Å3
Crystal data top
[CuSm(C20H22N2O4)(NO3)3]V = 2564.3 (9) Å3
Mr = 754.32Z = 4
Monoclinic, P21/nMo Kα radiation
a = 11.764 (2) ŵ = 3.17 mm1
b = 14.786 (3) ÅT = 295 K
c = 15.004 (3) Å0.24 × 0.18 × 0.15 mm
β = 100.73 (3)°
Data collection top
Rigaku R-AXIS RAPID CCD
diffractometer
5855 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
5046 reflections with I > 2σ(I)
Tmin = 0.516, Tmax = 0.648Rint = 0.037
24339 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0260 restraints
wR(F2) = 0.062H-atom parameters constrained
S = 1.04Δρmax = 0.77 e Å3
5855 reflectionsΔρmin = 0.38 e Å3
373 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*/UeqOcc. (<1)
Sm10.259064 (11)0.250880 (8)0.565440 (9)0.03052 (5)
Cu10.54988 (3)0.26907 (2)0.53542 (2)0.03185 (8)
O10.25817 (15)0.40859 (13)0.64009 (13)0.0407 (4)
O20.43419 (14)0.34352 (11)0.57697 (12)0.0339 (4)
O30.41124 (15)0.19822 (12)0.49482 (13)0.0384 (4)
O40.20146 (16)0.16351 (14)0.41214 (13)0.0439 (5)
O50.07423 (16)0.32911 (14)0.50534 (14)0.0471 (5)
O60.21496 (18)0.36420 (14)0.43857 (14)0.0495 (5)
O70.0562 (2)0.4400 (2)0.4088 (2)0.0954 (10)
O80.08550 (17)0.14963 (15)0.57011 (15)0.0531 (5)
O90.25342 (19)0.08703 (14)0.59909 (16)0.0531 (5)
O100.1007 (3)0.00645 (17)0.6032 (2)0.0905 (9)
O110.3947 (3)0.2257 (2)0.7125 (2)0.0969 (11)
O120.2166 (3)0.23958 (16)0.72203 (19)0.0736 (8)
O130.317 (4)0.256 (3)0.8441 (11)0.101 (9)0.45 (7)
O13'0.367 (3)0.206 (4)0.8420 (12)0.123 (12)0.55 (7)
N10.66513 (18)0.36617 (14)0.55494 (14)0.0327 (5)
N20.64898 (19)0.16474 (15)0.51218 (16)0.0395 (5)
N30.1128 (2)0.37923 (17)0.44897 (18)0.0485 (6)
N40.1437 (2)0.07931 (17)0.59096 (17)0.0505 (6)
N50.3202 (5)0.2317 (3)0.7614 (2)0.1070 (18)
C10.1677 (3)0.4401 (2)0.6854 (2)0.0593 (9)
H1A0.20000.45390.74750.089*
H1B0.11000.39380.68330.089*
H1C0.13300.49340.65570.089*
C20.3512 (2)0.46618 (17)0.64170 (16)0.0320 (5)
C30.3556 (2)0.55389 (18)0.67252 (18)0.0402 (6)
H3A0.29310.57810.69430.048*
C40.4534 (3)0.60651 (18)0.67108 (19)0.0423 (6)
H4A0.45550.66620.69080.051*
C50.5459 (2)0.57090 (17)0.64095 (18)0.0374 (6)
H5A0.61120.60620.64090.045*
C60.5435 (2)0.48049 (16)0.60967 (16)0.0299 (5)
C70.4445 (2)0.42749 (16)0.60824 (15)0.0279 (5)
C80.6461 (2)0.44643 (17)0.58155 (16)0.0325 (5)
H8A0.70610.48770.58280.039*
C90.7817 (2)0.3491 (2)0.5359 (2)0.0442 (7)
H9A0.81720.40600.52390.053*
H9B0.77610.31130.48240.053*
C100.8564 (2)0.3025 (2)0.6165 (2)0.0538 (8)
H10A0.93320.29300.60330.065*
H10B0.86380.34180.66900.065*
C110.8077 (3)0.2122 (3)0.6393 (2)0.0570 (8)
H11A0.86540.18100.68330.068*
H11B0.74080.22280.66720.068*
C120.7726 (2)0.1522 (2)0.5577 (2)0.0531 (8)
H12A0.82220.16480.51430.064*
H12B0.78440.08960.57630.064*
C130.6102 (2)0.10028 (19)0.4572 (2)0.0447 (7)
H13A0.66410.05720.44730.054*
C140.4936 (2)0.08675 (18)0.40927 (19)0.0391 (6)
C150.4736 (3)0.0181 (2)0.3426 (2)0.0494 (7)
H15A0.53540.01520.32930.059*
C160.3637 (3)0.0005 (2)0.2974 (2)0.0539 (8)
H16A0.35160.04390.25280.065*
C170.2701 (3)0.0484 (2)0.31751 (19)0.0481 (7)
H17A0.19580.03650.28600.058*
C180.2879 (2)0.11355 (18)0.38434 (17)0.0371 (6)
C190.3997 (2)0.13440 (17)0.43070 (17)0.0340 (5)
C200.0871 (3)0.1558 (3)0.3594 (3)0.0689 (10)
H20A0.08810.17250.29780.103*
H20B0.03580.19520.38390.103*
H20C0.06090.09440.36130.103*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sm10.02418 (8)0.03020 (8)0.03794 (8)0.00118 (5)0.00772 (5)0.00061 (5)
Cu10.02343 (15)0.03144 (15)0.04145 (17)0.00075 (12)0.00804 (12)0.00423 (13)
O10.0304 (10)0.0415 (10)0.0548 (11)0.0022 (8)0.0197 (8)0.0107 (9)
O20.0270 (9)0.0300 (9)0.0474 (10)0.0026 (7)0.0136 (8)0.0075 (8)
O30.0270 (9)0.0374 (10)0.0518 (11)0.0039 (8)0.0099 (8)0.0142 (8)
O40.0307 (10)0.0502 (12)0.0477 (11)0.0013 (9)0.0005 (8)0.0100 (9)
O50.0328 (10)0.0522 (12)0.0572 (12)0.0006 (9)0.0102 (9)0.0127 (10)
O60.0443 (12)0.0477 (12)0.0592 (13)0.0025 (10)0.0168 (10)0.0125 (10)
O70.0728 (18)0.084 (2)0.127 (2)0.0257 (15)0.0114 (17)0.0594 (19)
O80.0372 (11)0.0511 (13)0.0710 (14)0.0051 (10)0.0099 (10)0.0080 (11)
O90.0499 (13)0.0390 (11)0.0714 (14)0.0056 (9)0.0141 (11)0.0060 (10)
O100.111 (2)0.0542 (15)0.104 (2)0.0436 (16)0.0121 (18)0.0118 (15)
O110.076 (2)0.134 (3)0.0671 (18)0.0499 (19)0.0231 (16)0.0412 (18)
O120.106 (3)0.0643 (16)0.0575 (15)0.0322 (15)0.0338 (16)0.0022 (12)
O130.139 (13)0.130 (16)0.032 (4)0.053 (14)0.006 (5)0.012 (5)
O13'0.129 (13)0.17 (2)0.052 (4)0.086 (15)0.024 (6)0.047 (8)
N10.0280 (11)0.0337 (11)0.0384 (11)0.0037 (9)0.0110 (9)0.0010 (9)
N20.0279 (11)0.0384 (12)0.0541 (14)0.0034 (9)0.0123 (10)0.0035 (11)
N30.0422 (14)0.0422 (13)0.0590 (16)0.0010 (11)0.0038 (12)0.0112 (12)
N40.0619 (17)0.0402 (14)0.0485 (14)0.0158 (13)0.0080 (12)0.0000 (11)
N50.139 (4)0.128 (3)0.0450 (18)0.100 (3)0.005 (2)0.018 (2)
C10.0386 (17)0.066 (2)0.081 (2)0.0029 (15)0.0313 (16)0.0225 (18)
C20.0305 (13)0.0332 (13)0.0331 (12)0.0017 (10)0.0082 (10)0.0022 (10)
C30.0394 (15)0.0387 (14)0.0439 (15)0.0068 (12)0.0115 (12)0.0079 (12)
C40.0455 (16)0.0306 (13)0.0506 (16)0.0007 (12)0.0085 (13)0.0102 (12)
C50.0396 (15)0.0316 (13)0.0395 (14)0.0057 (11)0.0038 (11)0.0040 (11)
C60.0293 (12)0.0305 (12)0.0293 (12)0.0020 (10)0.0043 (10)0.0003 (10)
C70.0295 (12)0.0279 (11)0.0258 (11)0.0006 (10)0.0039 (9)0.0005 (9)
C80.0276 (12)0.0353 (13)0.0347 (13)0.0068 (10)0.0065 (10)0.0017 (11)
C90.0352 (15)0.0410 (15)0.0624 (18)0.0061 (12)0.0248 (13)0.0020 (13)
C100.0262 (14)0.067 (2)0.068 (2)0.0005 (14)0.0084 (14)0.0153 (17)
C110.0349 (16)0.079 (2)0.0551 (19)0.0086 (16)0.0026 (14)0.0160 (18)
C120.0307 (15)0.0438 (17)0.083 (2)0.0058 (12)0.0060 (15)0.0105 (16)
C130.0401 (15)0.0364 (14)0.0628 (19)0.0057 (12)0.0230 (14)0.0036 (13)
C140.0412 (15)0.0339 (13)0.0456 (15)0.0029 (11)0.0170 (12)0.0035 (11)
C150.062 (2)0.0406 (15)0.0518 (17)0.0009 (14)0.0264 (15)0.0087 (13)
C160.072 (2)0.0494 (18)0.0438 (16)0.0061 (16)0.0190 (15)0.0171 (14)
C170.0563 (18)0.0505 (17)0.0362 (14)0.0104 (14)0.0058 (13)0.0070 (13)
C180.0398 (15)0.0363 (14)0.0357 (13)0.0030 (11)0.0087 (11)0.0018 (11)
C190.0381 (14)0.0294 (12)0.0360 (13)0.0033 (11)0.0105 (11)0.0039 (10)
C200.0398 (18)0.085 (3)0.073 (2)0.0021 (17)0.0112 (16)0.019 (2)
Geometric parameters (Å, º) top
Sm1—O32.3748 (18)C1—H1C0.9600
Sm1—O22.4532 (17)C2—C31.375 (3)
Sm1—O92.478 (2)C2—C71.410 (3)
Sm1—O52.480 (2)C3—C41.393 (4)
Sm1—O122.497 (3)C3—H3A0.9300
Sm1—O112.499 (3)C4—C51.359 (4)
Sm1—O62.516 (2)C4—H4A0.9300
Sm1—O82.543 (2)C5—C61.415 (3)
Sm1—O12.5879 (19)C5—H5A0.9300
Sm1—O42.6151 (19)C6—C71.401 (3)
Sm1—N52.908 (3)C6—C81.442 (3)
Sm1—N32.915 (2)C8—H8A0.9300
Cu1—O31.9388 (18)C9—C101.521 (4)
Cu1—O21.9412 (17)C9—H9A0.9700
Cu1—N11.959 (2)C9—H9B0.9700
Cu1—N22.003 (2)C10—C111.517 (5)
O1—C21.384 (3)C10—H10A0.9700
O1—C11.443 (3)C10—H10B0.9700
O2—C71.325 (3)C11—C121.506 (5)
O3—C191.337 (3)C11—H11A0.9700
O4—C181.382 (3)C11—H11B0.9700
O4—C201.432 (3)C12—H12A0.9700
O5—N31.270 (3)C12—H12B0.9700
O6—N31.260 (3)C13—C141.439 (4)
O7—N31.210 (3)C13—H13A0.9300
O8—N41.252 (3)C14—C191.397 (4)
O9—N41.278 (3)C14—C151.413 (4)
O10—N41.219 (3)C15—C161.368 (4)
O11—N51.246 (6)C15—H15A0.9300
O12—N51.258 (6)C16—C171.388 (4)
O13—N51.298 (14)C16—H16A0.9300
O13'—N51.292 (15)C17—C181.378 (4)
N1—C81.285 (3)C17—H17A0.9300
N1—C91.474 (3)C18—C191.404 (4)
N2—C131.287 (4)C20—H20A0.9600
N2—C121.498 (3)C20—H20B0.9600
C1—H1A0.9600C20—H20C0.9600
C1—H1B0.9600
O3—Sm1—O261.42 (6)O7—N3—O6121.2 (3)
O3—Sm1—O979.71 (7)O7—N3—O5122.2 (3)
O2—Sm1—O9125.84 (7)O6—N3—O5116.5 (2)
O3—Sm1—O5132.34 (7)O7—N3—Sm1172.1 (2)
O2—Sm1—O5115.67 (6)O6—N3—Sm159.28 (13)
O9—Sm1—O5118.37 (7)O5—N3—Sm157.66 (13)
O3—Sm1—O12134.22 (10)O10—N4—O8123.3 (3)
O2—Sm1—O12106.48 (8)O10—N4—O9120.3 (3)
O9—Sm1—O1274.05 (8)O8—N4—O9116.4 (2)
O5—Sm1—O1293.31 (10)O10—N4—Sm1177.0 (3)
O3—Sm1—O1186.26 (11)O8—N4—Sm159.64 (13)
O2—Sm1—O1168.35 (8)O9—N4—Sm156.80 (13)
O9—Sm1—O1173.23 (9)O11—N5—O12117.1 (3)
O5—Sm1—O11139.74 (11)O11—N5—O13'108 (2)
O12—Sm1—O1150.64 (12)O12—N5—O13'132.7 (16)
O3—Sm1—O686.98 (7)O11—N5—O13136.8 (15)
O2—Sm1—O674.56 (7)O12—N5—O13103 (2)
O9—Sm1—O6142.70 (7)O11—N5—Sm158.69 (18)
O5—Sm1—O651.02 (7)O12—N5—Sm158.66 (18)
O12—Sm1—O6135.00 (9)O13'—N5—Sm1163 (3)
O11—Sm1—O6140.81 (8)O13—N5—Sm1153 (3)
O3—Sm1—O8119.67 (7)O1—C1—H1A109.5
O2—Sm1—O8174.11 (6)O1—C1—H1B109.5
O9—Sm1—O850.72 (7)H1A—C1—H1B109.5
O5—Sm1—O868.32 (7)O1—C1—H1C109.5
O12—Sm1—O868.43 (9)H1A—C1—H1C109.5
O11—Sm1—O8105.78 (9)H1B—C1—H1C109.5
O6—Sm1—O8111.05 (7)C3—C2—O1124.5 (2)
O3—Sm1—O1123.55 (6)C3—C2—C7121.3 (2)
O2—Sm1—O162.44 (6)O1—C2—C7114.2 (2)
O9—Sm1—O1142.22 (7)C2—C3—C4120.1 (3)
O5—Sm1—O170.31 (7)C2—C3—H3A120.0
O12—Sm1—O168.62 (7)C4—C3—H3A120.0
O11—Sm1—O178.77 (10)C5—C4—C3120.2 (2)
O6—Sm1—O173.17 (7)C5—C4—H4A119.9
O8—Sm1—O1116.78 (7)C3—C4—H4A119.9
O3—Sm1—O462.55 (6)C4—C5—C6120.6 (3)
O2—Sm1—O4114.50 (6)C4—C5—H5A119.7
O9—Sm1—O471.57 (7)C6—C5—H5A119.7
O5—Sm1—O481.05 (7)C7—C6—C5119.9 (2)
O12—Sm1—O4136.89 (8)C7—C6—C8122.6 (2)
O11—Sm1—O4136.19 (10)C5—C6—C8117.4 (2)
O6—Sm1—O471.37 (7)O2—C7—C6123.4 (2)
O8—Sm1—O469.85 (7)O2—C7—C2118.7 (2)
O1—Sm1—O4143.57 (6)C6—C7—C2117.9 (2)
O3—Sm1—N5110.73 (13)N1—C8—C6128.1 (2)
O2—Sm1—N586.37 (9)N1—C8—H8A115.9
O9—Sm1—N573.12 (10)C6—C8—H8A115.9
O5—Sm1—N5116.63 (14)N1—C9—C10110.1 (2)
O12—Sm1—N525.48 (13)N1—C9—H9A109.6
O11—Sm1—N525.22 (14)C10—C9—H9A109.6
O6—Sm1—N5143.82 (10)N1—C9—H9B109.6
O8—Sm1—N587.91 (9)C10—C9—H9B109.6
O1—Sm1—N570.76 (10)H9A—C9—H9B108.2
O4—Sm1—N5144.69 (9)C11—C10—C9113.1 (2)
O3—Sm1—N3110.85 (7)C11—C10—H10A109.0
O2—Sm1—N394.19 (7)C9—C10—H10A109.0
O9—Sm1—N3136.33 (7)C11—C10—H10B109.0
O5—Sm1—N325.64 (7)C9—C10—H10B109.0
O12—Sm1—N3114.10 (10)H10A—C10—H10B107.8
O11—Sm1—N3146.62 (10)C12—C11—C10113.1 (3)
O6—Sm1—N325.50 (7)C12—C11—H11A109.0
O8—Sm1—N390.71 (7)C10—C11—H11A109.0
O1—Sm1—N367.87 (7)C12—C11—H11B109.0
O4—Sm1—N376.52 (7)C10—C11—H11B109.0
N5—Sm1—N3132.61 (13)H11A—C11—H11B107.8
O3—Cu1—O278.94 (7)N2—C12—C11113.2 (3)
O3—Cu1—N1164.02 (8)N2—C12—H12A108.9
O2—Cu1—N192.49 (8)C11—C12—H12A108.9
O3—Cu1—N290.69 (9)N2—C12—H12B108.9
O2—Cu1—N2163.38 (8)C11—C12—H12B108.9
N1—Cu1—N2100.45 (9)H12A—C12—H12B107.7
O3—Cu1—Sm139.03 (5)N2—C13—C14127.9 (3)
O2—Cu1—Sm141.49 (5)N2—C13—H13A116.0
N1—Cu1—Sm1133.98 (6)C14—C13—H13A116.0
N2—Cu1—Sm1124.80 (7)C19—C14—C15119.3 (3)
C2—O1—C1116.4 (2)C19—C14—C13122.4 (2)
C2—O1—Sm1119.68 (14)C15—C14—C13118.1 (3)
C1—O1—Sm1123.88 (17)C16—C15—C14120.3 (3)
C7—O2—Cu1128.45 (15)C16—C15—H15A119.8
C7—O2—Sm1124.64 (14)C14—C15—H15A119.8
Cu1—O2—Sm1106.89 (7)C15—C16—C17120.7 (3)
C19—O3—Cu1125.05 (16)C15—C16—H16A119.7
C19—O3—Sm1124.68 (15)C17—C16—H16A119.7
Cu1—O3—Sm1110.04 (8)C18—C17—C16119.7 (3)
C18—O4—C20117.3 (2)C18—C17—H17A120.2
C18—O4—Sm1116.40 (15)C16—C17—H17A120.2
C20—O4—Sm1126.02 (19)C17—C18—O4125.0 (3)
N3—O5—Sm196.70 (15)C17—C18—C19121.0 (3)
N3—O6—Sm195.21 (16)O4—C18—C19114.0 (2)
N4—O8—Sm195.22 (16)O3—C19—C14122.9 (2)
N4—O9—Sm197.63 (16)O3—C19—C18118.1 (2)
N5—O11—Sm196.1 (3)C14—C19—C18118.9 (2)
N5—O12—Sm195.9 (3)O4—C20—H20A109.5
C8—N1—C9116.1 (2)O4—C20—H20B109.5
C8—N1—Cu1124.59 (18)H20A—C20—H20B109.5
C9—N1—Cu1119.26 (17)O4—C20—H20C109.5
C13—N2—C12113.5 (2)H20A—C20—H20C109.5
C13—N2—Cu1122.24 (19)H20B—C20—H20C109.5
C12—N2—Cu1124.24 (19)
O2—Sm1—Cu1—O3159.24 (12)O5—Sm1—O11—N528.5 (3)
O9—Sm1—Cu1—O351.08 (11)O12—Sm1—O11—N53.0 (2)
O5—Sm1—Cu1—O398.96 (12)O6—Sm1—O11—N5113.2 (2)
O12—Sm1—Cu1—O3127.99 (11)O8—Sm1—O11—N546.4 (3)
O11—Sm1—Cu1—O3119.13 (13)O1—Sm1—O11—N568.5 (3)
O6—Sm1—Cu1—O391.65 (11)O4—Sm1—O11—N5123.6 (3)
O8—Sm1—Cu1—O331.90 (13)N3—Sm1—O11—N570.4 (3)
O1—Sm1—Cu1—O3164.40 (10)O3—Sm1—O12—N526.6 (3)
O4—Sm1—Cu1—O320.46 (10)O2—Sm1—O12—N539.3 (3)
N5—Sm1—Cu1—O3124.64 (13)O9—Sm1—O12—N584.1 (2)
N3—Sm1—Cu1—O396.58 (11)O5—Sm1—O12—N5157.3 (2)
O3—Sm1—Cu1—O2159.24 (12)O11—Sm1—O12—N53.0 (2)
O9—Sm1—Cu1—O2149.68 (10)O6—Sm1—O12—N5123.7 (2)
O5—Sm1—Cu1—O260.28 (11)O8—Sm1—O12—N5137.6 (3)
O12—Sm1—Cu1—O272.77 (10)O1—Sm1—O12—N589.9 (2)
O11—Sm1—Cu1—O281.64 (12)O4—Sm1—O12—N5122.3 (2)
O6—Sm1—Cu1—O267.59 (10)N3—Sm1—O12—N5141.7 (2)
O8—Sm1—Cu1—O2168.86 (12)O3—Cu1—N1—C853.8 (4)
O1—Sm1—Cu1—O25.16 (9)O2—Cu1—N1—C83.2 (2)
O4—Sm1—Cu1—O2138.78 (9)N2—Cu1—N1—C8172.7 (2)
N5—Sm1—Cu1—O276.12 (12)Sm1—Cu1—N1—C82.8 (3)
N3—Sm1—Cu1—O262.66 (10)O3—Cu1—N1—C9124.4 (3)
O3—Sm1—Cu1—N1158.61 (13)O2—Cu1—N1—C9178.70 (19)
O2—Sm1—Cu1—N10.63 (12)N2—Cu1—N1—C99.2 (2)
O9—Sm1—Cu1—N1150.32 (10)Sm1—Cu1—N1—C9179.12 (15)
O5—Sm1—Cu1—N159.64 (11)O3—Cu1—N2—C1321.8 (2)
O12—Sm1—Cu1—N173.40 (11)O2—Cu1—N2—C1372.8 (4)
O11—Sm1—Cu1—N182.27 (13)N1—Cu1—N2—C13146.6 (2)
O6—Sm1—Cu1—N166.96 (10)Sm1—Cu1—N2—C1342.2 (3)
O8—Sm1—Cu1—N1169.49 (13)O3—Cu1—N2—C12156.5 (2)
O1—Sm1—Cu1—N15.79 (10)O2—Cu1—N2—C12105.5 (3)
O4—Sm1—Cu1—N1138.14 (10)N1—Cu1—N2—C1235.0 (2)
N5—Sm1—Cu1—N176.75 (13)Sm1—Cu1—N2—C12136.2 (2)
N3—Sm1—Cu1—N162.03 (10)Sm1—O6—N3—O7170.8 (3)
O3—Sm1—Cu1—N233.46 (12)Sm1—O6—N3—O57.2 (3)
O2—Sm1—Cu1—N2167.30 (12)Sm1—O5—N3—O7170.7 (3)
O9—Sm1—Cu1—N217.62 (10)Sm1—O5—N3—O67.4 (3)
O5—Sm1—Cu1—N2132.42 (11)O3—Sm1—N3—O621.65 (18)
O12—Sm1—Cu1—N294.53 (11)O2—Sm1—N3—O639.32 (17)
O11—Sm1—Cu1—N285.66 (12)O9—Sm1—N3—O6118.66 (17)
O6—Sm1—Cu1—N2125.11 (10)O5—Sm1—N3—O6172.3 (3)
O8—Sm1—Cu1—N21.56 (13)O12—Sm1—N3—O6149.46 (16)
O1—Sm1—Cu1—N2162.14 (9)O11—Sm1—N3—O695.2 (2)
O4—Sm1—Cu1—N253.93 (9)O8—Sm1—N3—O6143.95 (17)
N5—Sm1—Cu1—N291.18 (12)O1—Sm1—N3—O697.27 (17)
N3—Sm1—Cu1—N2130.04 (10)O4—Sm1—N3—O674.89 (17)
O3—Sm1—O1—C21.4 (2)N5—Sm1—N3—O6128.24 (18)
O2—Sm1—O1—C25.10 (16)O3—Sm1—N3—O5150.69 (16)
O9—Sm1—O1—C2118.97 (18)O2—Sm1—N3—O5148.34 (16)
O5—Sm1—O1—C2129.79 (18)O9—Sm1—N3—O553.7 (2)
O12—Sm1—O1—C2128.3 (2)O12—Sm1—N3—O538.20 (18)
O11—Sm1—O1—C276.39 (18)O11—Sm1—N3—O592.5 (2)
O6—Sm1—O1—C275.93 (18)O6—Sm1—N3—O5172.3 (3)
O8—Sm1—O1—C2178.54 (16)O8—Sm1—N3—O528.39 (17)
O4—Sm1—O1—C289.52 (19)O1—Sm1—N3—O590.39 (17)
N5—Sm1—O1—C2101.2 (2)O4—Sm1—N3—O597.45 (17)
N3—Sm1—O1—C2102.43 (18)N5—Sm1—N3—O559.4 (2)
O3—Sm1—O1—C1178.1 (2)Sm1—O8—N4—O10179.3 (3)
O2—Sm1—O1—C1171.6 (2)Sm1—O8—N4—O90.7 (3)
O9—Sm1—O1—C157.7 (3)Sm1—O9—N4—O10179.3 (3)
O5—Sm1—O1—C153.5 (2)Sm1—O9—N4—O80.8 (3)
O12—Sm1—O1—C148.4 (2)O3—Sm1—N4—O8142.62 (17)
O11—Sm1—O1—C1100.3 (2)O2—Sm1—N4—O8169.89 (15)
O6—Sm1—O1—C1107.4 (2)O9—Sm1—N4—O8179.2 (3)
O8—Sm1—O1—C11.8 (2)O5—Sm1—N4—O88.53 (18)
O4—Sm1—O1—C193.8 (2)O12—Sm1—N4—O883.81 (19)
N5—Sm1—O1—C175.5 (2)O11—Sm1—N4—O8131.28 (19)
N3—Sm1—O1—C180.9 (2)O6—Sm1—N4—O847.9 (2)
O3—Cu1—O2—C7168.4 (2)O1—Sm1—N4—O857.26 (19)
N1—Cu1—O2—C72.0 (2)O4—Sm1—N4—O887.65 (17)
N2—Cu1—O2—C7139.3 (3)N5—Sm1—N4—O8108.0 (2)
Sm1—Cu1—O2—C7178.4 (2)N3—Sm1—N4—O824.14 (19)
O3—Cu1—O2—Sm113.15 (8)O3—Sm1—N4—O936.59 (18)
N1—Cu1—O2—Sm1179.54 (8)O2—Sm1—N4—O910.9 (3)
N2—Cu1—O2—Sm139.1 (3)O5—Sm1—N4—O9170.68 (17)
O3—Sm1—O2—C7169.5 (2)O12—Sm1—N4—O996.99 (19)
O9—Sm1—O2—C7140.60 (17)O11—Sm1—N4—O949.52 (19)
O5—Sm1—O2—C743.43 (19)O6—Sm1—N4—O9131.30 (17)
O12—Sm1—O2—C758.64 (19)O8—Sm1—N4—O9179.2 (3)
O11—Sm1—O2—C792.6 (2)O1—Sm1—N4—O9123.54 (17)
O6—Sm1—O2—C774.46 (18)O4—Sm1—N4—O991.56 (18)
O1—Sm1—O2—C74.31 (16)N5—Sm1—N4—O972.8 (2)
O4—Sm1—O2—C7135.11 (17)N3—Sm1—N4—O9155.07 (17)
N5—Sm1—O2—C774.5 (2)Sm1—O11—N5—O125.2 (4)
N3—Sm1—O2—C758.02 (18)Sm1—O11—N5—O13'169 (2)
O3—Sm1—O2—Cu111.98 (7)Sm1—O11—N5—O13152 (3)
O9—Sm1—O2—Cu137.90 (12)Sm1—O12—N5—O115.2 (4)
O5—Sm1—O2—Cu1138.07 (8)Sm1—O12—N5—O13'164 (4)
O12—Sm1—O2—Cu1119.87 (10)Sm1—O12—N5—O13158.8 (16)
O11—Sm1—O2—Cu185.86 (13)O3—Sm1—N5—O1114.7 (3)
O6—Sm1—O2—Cu1107.04 (9)O2—Sm1—N5—O1142.9 (3)
O1—Sm1—O2—Cu1174.19 (10)O9—Sm1—N5—O1186.4 (3)
O4—Sm1—O2—Cu146.39 (10)O5—Sm1—N5—O11159.9 (3)
N5—Sm1—O2—Cu1104.03 (14)O12—Sm1—N5—O11174.6 (4)
N3—Sm1—O2—Cu1123.47 (9)O6—Sm1—N5—O11100.3 (4)
O2—Cu1—O3—C19160.8 (2)O8—Sm1—N5—O11135.7 (3)
N1—Cu1—O3—C19102.2 (3)O1—Sm1—N5—O11104.9 (3)
N2—Cu1—O3—C1932.3 (2)O4—Sm1—N5—O1186.1 (3)
Sm1—Cu1—O3—C19174.6 (3)N3—Sm1—N5—O11135.2 (3)
O2—Cu1—O3—Sm113.84 (8)O3—Sm1—N5—O12159.9 (2)
N1—Cu1—O3—Sm172.4 (3)O2—Sm1—N5—O12142.5 (2)
N2—Cu1—O3—Sm1153.08 (10)O9—Sm1—N5—O1288.2 (2)
O2—Sm1—O3—C19162.4 (2)O5—Sm1—N5—O1225.6 (3)
O9—Sm1—O3—C1956.63 (19)O11—Sm1—N5—O12174.6 (4)
O5—Sm1—O3—C1962.6 (2)O6—Sm1—N5—O1285.1 (2)
O12—Sm1—O3—C19112.1 (2)O8—Sm1—N5—O1238.9 (2)
O11—Sm1—O3—C19130.3 (2)O1—Sm1—N5—O1280.5 (2)
O6—Sm1—O3—C1988.4 (2)O4—Sm1—N5—O1288.5 (3)
O8—Sm1—O3—C1924.2 (2)N3—Sm1—N5—O1250.2 (2)
O1—Sm1—O3—C19155.86 (18)O3—Sm1—N5—O13'23 (2)
O4—Sm1—O3—C1917.83 (18)O2—Sm1—N5—O13'81 (2)
N5—Sm1—O3—C19124.0 (2)O9—Sm1—N5—O13'49 (2)
N3—Sm1—O3—C1979.2 (2)O5—Sm1—N5—O13'162 (2)
O2—Sm1—O3—Cu112.22 (7)O12—Sm1—N5—O13'137 (2)
O9—Sm1—O3—Cu1128.73 (10)O11—Sm1—N5—O13'38 (2)
O5—Sm1—O3—Cu1112.07 (10)O6—Sm1—N5—O13'138 (2)
O12—Sm1—O3—Cu173.23 (13)O8—Sm1—N5—O13'98 (2)
O11—Sm1—O3—Cu155.11 (11)O1—Sm1—N5—O13'143 (2)
O6—Sm1—O3—Cu186.26 (10)O4—Sm1—N5—O13'48 (2)
O8—Sm1—O3—Cu1161.16 (8)N3—Sm1—N5—O13'173 (2)
O1—Sm1—O3—Cu118.78 (12)O3—Sm1—N5—O13148.4 (16)
O4—Sm1—O3—Cu1156.81 (11)O2—Sm1—N5—O1390.8 (16)
N5—Sm1—O3—Cu161.33 (11)O9—Sm1—N5—O13140.0 (16)
N3—Sm1—O3—Cu195.42 (10)O5—Sm1—N5—O1326.2 (16)
O3—Sm1—O4—C1816.38 (17)O12—Sm1—N5—O1351.7 (16)
O2—Sm1—O4—C1850.38 (19)O11—Sm1—N5—O13133.7 (16)
O9—Sm1—O4—C1871.38 (18)O6—Sm1—N5—O1333.4 (16)
O5—Sm1—O4—C18164.60 (18)O8—Sm1—N5—O1390.6 (16)
O12—Sm1—O4—C18110.1 (2)O1—Sm1—N5—O1328.8 (16)
O11—Sm1—O4—C1833.3 (2)O4—Sm1—N5—O13140.2 (16)
O6—Sm1—O4—C18112.84 (18)N3—Sm1—N5—O131.5 (16)
O8—Sm1—O4—C18125.32 (19)C1—O1—C2—C38.8 (4)
O1—Sm1—O4—C18126.56 (17)Sm1—O1—C2—C3174.2 (2)
N5—Sm1—O4—C1871.2 (3)C1—O1—C2—C7171.3 (2)
N3—Sm1—O4—C18138.85 (19)Sm1—O1—C2—C75.6 (3)
O3—Sm1—O4—C20170.0 (3)O1—C2—C3—C4179.8 (2)
O2—Sm1—O4—C20136.0 (3)C7—C2—C3—C40.0 (4)
O9—Sm1—O4—C20102.2 (3)C2—C3—C4—C51.3 (4)
O5—Sm1—O4—C2021.8 (3)C3—C4—C5—C60.8 (4)
O12—Sm1—O4—C2063.5 (3)C4—C5—C6—C71.0 (4)
O11—Sm1—O4—C20140.3 (3)C4—C5—C6—C8178.0 (2)
O6—Sm1—O4—C2073.6 (3)Cu1—O2—C7—C65.3 (3)
O8—Sm1—O4—C2048.3 (3)Sm1—O2—C7—C6176.54 (16)
O1—Sm1—O4—C2059.8 (3)Cu1—O2—C7—C2174.92 (16)
N5—Sm1—O4—C20102.4 (3)Sm1—O2—C7—C23.2 (3)
N3—Sm1—O4—C2047.6 (3)C5—C6—C7—O2177.5 (2)
O3—Sm1—O5—N338.23 (19)C8—C6—C7—O23.5 (4)
O2—Sm1—O5—N335.50 (18)C5—C6—C7—C22.3 (3)
O9—Sm1—O5—N3140.79 (16)C8—C6—C7—C2176.7 (2)
O12—Sm1—O5—N3145.57 (17)C3—C2—C7—O2178.1 (2)
O11—Sm1—O5—N3121.73 (18)O1—C2—C7—O21.8 (3)
O6—Sm1—O5—N34.23 (15)C3—C2—C7—C61.7 (4)
O8—Sm1—O5—N3149.23 (18)O1—C2—C7—C6178.4 (2)
O1—Sm1—O5—N379.68 (16)C9—N1—C8—C6176.2 (2)
O4—Sm1—O5—N377.45 (17)Cu1—N1—C8—C65.7 (4)
N5—Sm1—O5—N3134.86 (17)C7—C6—C8—N12.4 (4)
O3—Sm1—O6—N3159.81 (17)C5—C6—C8—N1176.6 (2)
O2—Sm1—O6—N3139.04 (17)C8—N1—C9—C1098.8 (3)
O9—Sm1—O6—N391.2 (2)Cu1—N1—C9—C1083.0 (3)
O5—Sm1—O6—N34.26 (15)N1—C9—C10—C1160.0 (3)
O12—Sm1—O6—N341.0 (2)C9—C10—C11—C1248.2 (4)
O11—Sm1—O6—N3119.9 (2)C13—N2—C12—C11164.1 (3)
O8—Sm1—O6—N339.08 (18)Cu1—N2—C12—C1114.4 (4)
O1—Sm1—O6—N373.74 (16)C10—C11—C12—N290.6 (3)
O4—Sm1—O6—N397.79 (17)C12—N2—C13—C14173.8 (3)
N5—Sm1—O6—N378.3 (3)Cu1—N2—C13—C144.7 (4)
O3—Sm1—O8—N443.42 (19)N2—C13—C14—C1913.2 (5)
O9—Sm1—O8—N40.44 (16)N2—C13—C14—C15171.3 (3)
O5—Sm1—O8—N4170.83 (19)C19—C14—C15—C162.1 (4)
O12—Sm1—O8—N486.22 (18)C13—C14—C15—C16177.7 (3)
O11—Sm1—O8—N451.3 (2)C14—C15—C16—C171.2 (5)
O6—Sm1—O8—N4142.29 (16)C15—C16—C17—C180.8 (5)
O1—Sm1—O8—N4136.52 (16)C16—C17—C18—O4178.0 (3)
O4—Sm1—O8—N482.69 (17)C16—C17—C18—C192.0 (4)
N5—Sm1—O8—N469.3 (2)C20—O4—C18—C178.9 (4)
N3—Sm1—O8—N4158.04 (17)Sm1—O4—C18—C17165.2 (2)
O3—Sm1—O9—N4143.42 (18)C20—O4—C18—C19171.1 (3)
O2—Sm1—O9—N4173.54 (15)Sm1—O4—C18—C1914.7 (3)
O5—Sm1—O9—N410.6 (2)Cu1—O3—C19—C1425.2 (4)
O12—Sm1—O9—N474.48 (19)Sm1—O3—C19—C14161.0 (2)
O11—Sm1—O9—N4127.4 (2)Cu1—O3—C19—C18156.08 (19)
O6—Sm1—O9—N472.5 (2)Sm1—O3—C19—C1817.8 (3)
O8—Sm1—O9—N40.44 (15)C15—C14—C19—O3177.9 (3)
O1—Sm1—O9—N483.5 (2)C13—C14—C19—O32.5 (4)
O4—Sm1—O9—N479.10 (17)C15—C14—C19—C180.9 (4)
N5—Sm1—O9—N4101.0 (2)C13—C14—C19—C18176.3 (3)
N3—Sm1—O9—N433.9 (2)C17—C18—C19—O3180.0 (2)
O3—Sm1—O11—N5166.3 (3)O4—C18—C19—O30.0 (4)
O2—Sm1—O11—N5133.1 (3)C17—C18—C19—C141.2 (4)
O9—Sm1—O11—N585.9 (3)O4—C18—C19—C14178.8 (2)

Experimental details

Crystal data
Chemical formula[CuSm(C20H22N2O4)(NO3)3]
Mr754.32
Crystal system, space groupMonoclinic, P21/n
Temperature (K)295
a, b, c (Å)11.764 (2), 14.786 (3), 15.004 (3)
β (°) 100.73 (3)
V3)2564.3 (9)
Z4
Radiation typeMo Kα
µ (mm1)3.17
Crystal size (mm)0.24 × 0.18 × 0.15
Data collection
DiffractometerRigaku R-AXIS RAPID CCD
diffractometer
Absorption correctionMulti-scan
(ABSCOR; Higashi, 1995)
Tmin, Tmax0.516, 0.648
No. of measured, independent and
observed [I > 2σ(I)] reflections
24339, 5855, 5046
Rint0.037
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.026, 0.062, 1.04
No. of reflections5855
No. of parameters373
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.77, 0.38

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

 

Acknowledgements

The authors gratefully acknowledge financial support of this work by the Project of Hei Long Jiang Provincial Health Office (No. 2010–077) and the Heilongjiang Key Laboratory of Anesthesia and Critical Care Research.

References

First citationHigashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationRigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationRigaku/MSC (2002). CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationXing, J.-C., Cui, X.-G., Zhang, B. & Li, W.-Z. (2010). Acta Cryst. E66, m1423.  CrossRef IUCr Journals Google Scholar
First citationXing, J.-C., Xu, Y.-M., Cui, X.-G. & Li, W.-Z. (2009). Acta Cryst. E65, m443.  Web of Science CSD CrossRef IUCr Journals Google Scholar

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