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Acta Cryst. (2009). E65, m1360    [ doi:10.1107/S1600536809040628 ]

Bis([mu]-biphenyl-2,2'-dicarboxylato)bis[aqua(4,4'-dimethyl-2,2'-bipyridine-[kappa]2N,N')copper(II)]

X.-Y. Dong, X.-J. Xu and L. Yang

Abstract top

The molecule of the title binuclear copper(II) complex, [Cu2(C14H8O4)2(C12H12N2)2(H2O)2], is bisected by a crystallographic twofold axis. Each CuII atom is coordinated in a distorted octahedral geometry by three O atoms from two biphenyl-2,2'-dicarboxylate anions, one aqua O atom and two N atoms of a 4,4'-dimethyl-2,2'-bipyridine ligand. Intramolecular O-H...O hydrogen bonds between the coordinated water molecules and the carboxylate O atoms are also present.

Comment top

The title binuclear copper(II) complex, [Cu2(C14H8O4)2(C10H8N2)2(H2O)2], is a centrosymmetric dimer. The asymmetric unit consitsts of one CuII atom, one 4,4'-dimethyl-2,2'-bipyridine (dbpy) ligand, one [1,1'-biphenyl]-2,2'-dicarboxylate dianion (bpdc2-) and a coordinated water molecule.

The CuII atom is six-coordinated by two N atoms from bpy and four O atoms, three from two bpdc2- anions and one from coordinated H2O, in a distorted octahedron coordination geometry. And it is noteworthy that the two CuII ions in the complex are bridged by two bpdc2- dianions, one is in a bis-monodentate mode whereas the other is in a bis-bidentate mode.

Related literature top

For related structures, see: Li et al. (2009); Jiang & Feng (2009); Xu et al. (2009); Zhang et al. (2009); Rizal & Ng (2009); Zhang (2009).

Experimental top

The title complound was synthesized hydrothermally in a Teflon-lined autoclave (25 ml) by heating a mixture of H2bpdc (0.2 mmol), dbpy (0.4 mmol) and CuSO4.5H2O (0.2 mmol) in water (10 ml) at 393 K for 3 d. Crystals suitable for X-ray analysis were obtained.

Refinement top

All H atoms were included in calculated positions, with C—H bond lengths fixed at 0.96 Å (methyl CH3), 0.93Å (aryl group) and O—H = 0.85 Å and were refined in the riding-model approximation. Uiso(H) values were calculated at 1.5 Ueq(C) for methyl groups and 1.2 Ueq(C) otherwise.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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 of the title compound with the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are presented as small spheres of arbitrary radius. Hydrogen-bond interactions are drawn with dashed lines. Atoms labeled(i) are generated by the symmetry code -x, y, -z + 1/2.
Bis(µ-biphenyl-2,2'-dicarboxylato)bis[aqua(4,4'-dimethyl-2,2'- bipyridine)copper(II)] top
Crystal data top
[Cu2(C14H8O4)2(C12H12N2)2(H2O)2]F(000) = 2240
Mr = 1109.71Dx = 1.580 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 3688 reflections
a = 17.104 (3) Åθ = 2.7–27.3°
b = 15.395 (2) ŵ = 0.98 mm−1
c = 18.289 (3) ÅT = 296 K
β = 104.413 (3)°Block, colourless
V = 4664.2 (13) Å30.26 × 0.24 × 0.22 mm
Z = 4
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer		4594 independent reflections
Radiation source: fine-focus sealed tube3108 reflections with I > 2σ(I)
graphiteRint = 0.060
φ and ω scansθmax = 26.0°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		h = −21→20
Tmin = 0.785, Tmax = 0.814k = −18→12
13512 measured reflectionsl = −22→22
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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109H-atom parameters constrained
S = 0.93 w = 1/[σ2(Fo2) + (0.0562P)2]
where P = (Fo2 + 2Fc2)/3
4594 reflections(Δ/σ)max = 0.001
310 parametersΔρmax = 0.87 e Å−3
12 restraintsΔρmin = −0.33 e Å−3
Crystal data top
[Cu2(C14H8O4)2(C12H12N2)2(H2O)2]V = 4664.2 (13) Å3
Mr = 1109.71Z = 4
Monoclinic, C2/cMo Kα radiation
a = 17.104 (3) ŵ = 0.98 mm−1
b = 15.395 (2) ÅT = 296 K
c = 18.289 (3) Å0.26 × 0.24 × 0.22 mm
β = 104.413 (3)°
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer		4594 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		3108 reflections with I > 2σ(I)
Tmin = 0.785, Tmax = 0.814Rint = 0.060
13512 measured reflectionsθmax = 26.0°
Refinement top
R[F2 > 2σ(F2)] = 0.047H-atom parameters constrained
wR(F2) = 0.109Δρmax = 0.87 e Å−3
S = 0.93Δρmin = −0.33 e Å−3
4594 reflectionsAbsolute structure: ?
310 parametersFlack parameter: ?
12 restraintsRogers parameter: ?
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
Cd10.13088 (2)0.599652 (19)0.344239 (17)0.05361 (14)
N10.1810 (2)0.5542 (2)0.4686 (2)0.0615 (10)
N20.2592 (2)0.6574 (2)0.39215 (19)0.0516 (9)
O10.11652 (18)0.67905 (18)0.23068 (16)0.0602 (8)
O20.0871 (2)0.74927 (19)0.32546 (17)0.0611 (8)
O30.1387 (2)0.4729 (2)0.2927 (3)0.0977 (12)
O40.0538 (2)0.41826 (19)0.1917 (2)0.0701 (10)
O1W0.00362 (18)0.57274 (19)0.35468 (17)0.0611 (8)
H1WA−0.03260.61000.33650.073*
H1WB−0.01370.52340.33710.073*
C10.0942 (3)0.7474 (3)0.2590 (3)0.0527 (11)
C20.0782 (3)0.8273 (3)0.2111 (2)0.0537 (11)
C30.1193 (3)0.8370 (3)0.1546 (3)0.0677 (14)
H30.15450.79370.14730.081*
C40.1087 (4)0.9095 (3)0.1096 (3)0.0825 (17)
H40.13870.91610.07400.099*
C50.0541 (4)0.9725 (3)0.1166 (3)0.0813 (16)
H50.04551.02050.08480.098*
C60.0121 (3)0.9632 (3)0.1716 (3)0.0685 (14)
H6−0.02451.00600.17690.082*
C70.0232 (3)0.8913 (2)0.2195 (3)0.0540 (11)
C80.0959 (3)0.4138 (3)0.2577 (4)0.0675 (15)
C90.0975 (3)0.3293 (3)0.3005 (3)0.0578 (12)
C100.1638 (4)0.3135 (4)0.3615 (4)0.0935 (19)
H100.20470.35460.37470.112*
C110.1687 (5)0.2361 (5)0.4026 (4)0.114 (2)
H110.21440.22450.44110.137*
C120.1072 (5)0.1780 (4)0.3865 (4)0.101 (2)
H120.10960.12760.41510.121*
C130.0428 (3)0.1938 (3)0.3290 (3)0.0691 (14)
H130.00070.15380.31940.083*
C140.0357 (3)0.2671 (2)0.2827 (2)0.0491 (10)
C150.2960 (3)0.7114 (3)0.3534 (2)0.0619 (12)
H150.27250.71950.30230.074*
C160.3658 (3)0.7551 (3)0.3848 (3)0.0577 (12)
H160.38820.79250.35560.069*
C170.4026 (3)0.7432 (3)0.4598 (2)0.0523 (11)
C180.3652 (3)0.6872 (3)0.4998 (2)0.0514 (11)
H180.38820.67780.55080.062*
C190.2946 (3)0.6456 (2)0.4655 (2)0.0446 (10)
C200.2522 (3)0.5850 (2)0.5076 (3)0.0484 (11)
C210.2842 (3)0.5611 (3)0.5819 (3)0.0575 (12)
H210.33360.58400.60800.069*
C220.2441 (3)0.5040 (3)0.6179 (3)0.0589 (12)
C230.1719 (3)0.4713 (3)0.5762 (3)0.0750 (15)
H230.14350.43110.59740.090*
C240.1423 (3)0.4981 (3)0.5035 (3)0.0761 (15)
H240.09270.47630.47660.091*
C250.4800 (3)0.7895 (3)0.4962 (3)0.0717 (14)
H25A0.47030.85090.49600.108*
H25B0.51960.77740.46850.108*
H25C0.49940.76980.54730.108*
C260.2776 (3)0.4777 (4)0.6985 (3)0.0843 (16)
H26A0.31360.42940.70060.126*
H26B0.23420.46120.72030.126*
H26C0.30660.52560.72630.126*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cd10.0639 (3)0.0397 (2)0.0639 (2)−0.00834 (15)0.02867 (18)−0.00204 (16)
N10.068 (3)0.050 (2)0.073 (3)−0.012 (2)0.031 (2)0.012 (2)
N20.062 (2)0.044 (2)0.057 (2)−0.0098 (17)0.0290 (18)0.0006 (17)
O10.074 (2)0.0420 (17)0.073 (2)0.0006 (15)0.0356 (17)−0.0078 (15)
O20.078 (2)0.0476 (17)0.068 (2)0.0056 (15)0.0378 (17)0.0039 (15)
O30.087 (2)0.070 (2)0.150 (3)−0.021 (2)0.057 (2)−0.040 (2)
O40.084 (3)0.0377 (18)0.106 (3)−0.0016 (17)0.058 (2)−0.0019 (19)
O1W0.065 (2)0.0444 (16)0.080 (2)−0.0043 (15)0.0306 (17)−0.0008 (16)
C10.055 (3)0.039 (2)0.073 (3)−0.0036 (19)0.033 (2)0.001 (2)
C20.063 (3)0.042 (2)0.065 (3)−0.007 (2)0.032 (2)−0.002 (2)
C30.082 (4)0.054 (3)0.080 (3)−0.004 (3)0.045 (3)0.003 (3)
C40.113 (5)0.073 (4)0.078 (4)−0.014 (3)0.054 (3)0.009 (3)
C50.115 (5)0.050 (3)0.087 (4)−0.005 (3)0.040 (3)0.017 (3)
C60.088 (4)0.041 (3)0.083 (3)−0.002 (2)0.035 (3)0.008 (2)
C70.063 (3)0.035 (2)0.068 (3)−0.005 (2)0.025 (2)0.000 (2)
C80.062 (3)0.044 (3)0.116 (5)−0.009 (2)0.057 (3)−0.029 (3)
C90.058 (3)0.053 (3)0.069 (3)0.005 (2)0.027 (2)−0.026 (2)
C100.067 (4)0.093 (5)0.117 (5)0.003 (3)0.017 (4)−0.044 (4)
C110.116 (5)0.116 (5)0.093 (4)0.045 (5)−0.008 (4)−0.020 (4)
C120.125 (6)0.089 (5)0.082 (4)0.030 (4)0.013 (4)−0.001 (4)
C130.090 (4)0.052 (3)0.069 (3)0.017 (3)0.026 (3)0.003 (3)
C140.061 (3)0.035 (2)0.058 (3)0.0070 (19)0.0269 (19)−0.0053 (19)
C150.072 (3)0.065 (3)0.055 (3)−0.009 (3)0.029 (2)0.012 (2)
C160.066 (3)0.049 (3)0.068 (3)−0.010 (2)0.037 (3)0.008 (2)
C170.066 (3)0.036 (2)0.065 (3)−0.003 (2)0.036 (2)−0.004 (2)
C180.062 (3)0.047 (2)0.052 (2)−0.003 (2)0.027 (2)−0.003 (2)
C190.056 (3)0.032 (2)0.055 (3)0.0018 (19)0.031 (2)−0.0006 (19)
C200.056 (3)0.036 (2)0.062 (3)0.0020 (19)0.032 (2)0.001 (2)
C210.066 (3)0.052 (3)0.064 (3)−0.001 (2)0.034 (2)0.008 (2)
C220.069 (3)0.054 (3)0.068 (3)0.006 (2)0.042 (3)0.010 (2)
C230.083 (4)0.068 (3)0.087 (4)−0.013 (3)0.045 (3)0.025 (3)
C240.068 (3)0.070 (3)0.096 (4)−0.016 (3)0.030 (3)0.020 (3)
C250.077 (4)0.068 (3)0.077 (3)−0.023 (3)0.033 (3)−0.007 (3)
C260.106 (4)0.083 (4)0.079 (4)−0.003 (3)0.050 (3)0.022 (3)
Geometric parameters (Å, °) top
Cd1—O32.186 (4)C10—H100.9300
Cd1—O1W2.270 (3)C11—C121.357 (9)
Cd1—N22.327 (3)C11—H110.9300
Cd1—N12.329 (4)C12—C131.342 (8)
Cd1—O12.369 (3)C12—H120.9300
Cd1—O22.420 (3)C13—C141.397 (6)
N1—C201.335 (6)C13—H130.9300
N1—C241.343 (5)C14—C14i1.482 (8)
N2—C191.339 (5)C15—C161.366 (6)
N2—C151.346 (5)C15—H150.9300
O1—C11.272 (5)C16—C171.371 (6)
O2—C11.252 (5)C16—H160.9300
O3—C81.240 (6)C17—C181.386 (5)
O4—C81.244 (6)C17—C251.505 (6)
O1W—H1WA0.8498C18—C191.373 (6)
O1W—H1WB0.8499C18—H180.9300
C1—C21.495 (6)C19—C201.506 (5)
C2—C31.395 (6)C20—C211.382 (6)
C2—C71.397 (6)C21—C221.380 (6)
C3—C41.372 (6)C21—H210.9300
C3—H30.9300C22—C231.375 (7)
C4—C51.374 (7)C22—C261.499 (6)
C4—H40.9300C23—C241.364 (7)
C5—C61.382 (7)C23—H230.9300
C5—H50.9300C24—H240.9300
C6—C71.394 (6)C25—H25A0.9600
C6—H60.9300C25—H25B0.9600
C7—C7i1.524 (8)C25—H25C0.9600
C8—C91.515 (7)C26—H26A0.9600
C9—C101.400 (8)C26—H26B0.9600
C9—C141.403 (6)C26—H26C0.9600
C10—C111.400 (9)
O3—Cd1—O1W92.06 (12)C9—C10—H10119.9
O3—Cd1—N2110.50 (13)C12—C11—C10120.3 (6)
O1W—Cd1—N2150.70 (11)C12—C11—H11119.8
O3—Cd1—N196.06 (15)C10—C11—H11119.8
O1W—Cd1—N189.48 (12)C13—C12—C11119.4 (6)
N2—Cd1—N170.32 (12)C13—C12—H12120.3
O3—Cd1—O195.00 (13)C11—C12—H12120.3
O1W—Cd1—O1106.00 (11)C12—C13—C14123.5 (6)
N2—Cd1—O190.88 (11)C12—C13—H13118.2
N1—Cd1—O1160.61 (12)C14—C13—H13118.2
O3—Cd1—O2147.01 (15)C13—C14—C9117.6 (4)
O1W—Cd1—O285.21 (10)C13—C14—C14i114.8 (4)
N2—Cd1—O285.37 (12)C9—C14—C14i127.5 (3)
N1—Cd1—O2116.74 (12)N2—C15—C16123.9 (4)
O1—Cd1—O254.80 (9)N2—C15—H15118.0
C20—N1—C24117.8 (4)C16—C15—H15118.0
C20—N1—Cd1118.7 (3)C15—C16—C17119.3 (4)
C24—N1—Cd1123.5 (4)C15—C16—H16120.4
C19—N2—C15117.1 (4)C17—C16—H16120.4
C19—N2—Cd1118.3 (2)C16—C17—C18117.0 (4)
C15—N2—Cd1124.0 (3)C16—C17—C25120.9 (4)
C1—O1—Cd192.7 (2)C18—C17—C25122.1 (4)
C1—O2—Cd190.8 (2)C19—C18—C17121.2 (4)
C8—O3—Cd1141.8 (3)C19—C18—H18119.4
Cd1—O1W—H1WA117.7C17—C18—H18119.4
Cd1—O1W—H1WB112.5N2—C19—C18121.5 (4)
H1WA—O1W—H1WB107.7N2—C19—C20116.1 (4)
O2—C1—O1121.7 (4)C18—C19—C20122.4 (4)
O2—C1—C2120.2 (4)N1—C20—C21121.1 (4)
O1—C1—C2118.1 (4)N1—C20—C19115.9 (4)
C3—C2—C7118.8 (4)C21—C20—C19123.0 (4)
C3—C2—C1118.0 (4)C22—C21—C20121.1 (5)
C7—C2—C1123.1 (4)C22—C21—H21119.5
C4—C3—C2121.1 (5)C20—C21—H21119.5
C4—C3—H3119.5C23—C22—C21116.9 (4)
C2—C3—H3119.5C23—C22—C26121.2 (4)
C3—C4—C5120.7 (5)C21—C22—C26121.9 (5)
C3—C4—H4119.7C24—C23—C22119.7 (4)
C5—C4—H4119.7C24—C23—H23120.2
C4—C5—C6119.0 (5)C22—C23—H23120.2
C4—C5—H5120.5N1—C24—C23123.4 (5)
C6—C5—H5120.5N1—C24—H24118.3
C5—C6—C7121.6 (5)C23—C24—H24118.3
C5—C6—H6119.2C17—C25—H25A109.5
C7—C6—H6119.2C17—C25—H25B109.5
C6—C7—C2118.8 (4)H25A—C25—H25B109.5
C6—C7—C7i116.4 (3)C17—C25—H25C109.5
C2—C7—C7i124.6 (3)H25A—C25—H25C109.5
O3—C8—O4125.9 (6)H25B—C25—H25C109.5
O3—C8—C9115.5 (6)C22—C26—H26A109.5
O4—C8—C9118.7 (4)C22—C26—H26B109.5
C10—C9—C14118.7 (5)H26A—C26—H26B109.5
C10—C9—C8117.9 (5)C22—C26—H26C109.5
C14—C9—C8123.5 (4)H26A—C26—H26C109.5
C11—C10—C9120.3 (6)H26B—C26—H26C109.5
C11—C10—H10119.9
O3—Cd1—N1—C20113.7 (3)C1—C2—C7—C6−179.5 (4)
O1W—Cd1—N1—C20−154.3 (3)C3—C2—C7—C7i−177.3 (5)
N2—Cd1—N1—C204.0 (3)C1—C2—C7—C7i3.9 (8)
O1—Cd1—N1—C20−10.8 (6)Cd1—O3—C8—O469.7 (8)
O2—Cd1—N1—C20−69.9 (3)Cd1—O3—C8—C9−111.2 (6)
O3—Cd1—N1—C24−65.9 (4)O3—C8—C9—C10−21.7 (6)
O1W—Cd1—N1—C2426.1 (4)O4—C8—C9—C10157.6 (4)
N2—Cd1—N1—C24−175.6 (4)O3—C8—C9—C14157.5 (4)
O1—Cd1—N1—C24169.6 (3)O4—C8—C9—C14−23.3 (6)
O2—Cd1—N1—C24110.5 (4)C14—C9—C10—C111.4 (7)
O3—Cd1—N2—C19−95.8 (3)C8—C9—C10—C11−179.4 (5)
O1W—Cd1—N2—C1942.3 (4)C9—C10—C11—C12−3.8 (10)
N1—Cd1—N2—C19−6.6 (3)C10—C11—C12—C132.4 (10)
O1—Cd1—N2—C19168.5 (3)C11—C12—C13—C141.3 (9)
O2—Cd1—N2—C19114.0 (3)C12—C13—C14—C9−3.6 (7)
O3—Cd1—N2—C1593.2 (4)C12—C13—C14—C14i173.3 (5)
O1W—Cd1—N2—C15−128.7 (3)C10—C9—C14—C132.1 (6)
N1—Cd1—N2—C15−177.6 (4)C8—C9—C14—C13−177.0 (4)
O1—Cd1—N2—C15−2.5 (3)C10—C9—C14—C14i−174.3 (5)
O2—Cd1—N2—C15−57.1 (3)C8—C9—C14—C14i6.5 (7)
O3—Cd1—O1—C1166.2 (3)C19—N2—C15—C16−1.0 (7)
O1W—Cd1—O1—C172.6 (3)Cd1—N2—C15—C16170.2 (4)
N2—Cd1—O1—C1−83.1 (3)N2—C15—C16—C171.1 (7)
N1—Cd1—O1—C1−69.2 (4)C15—C16—C17—C18−0.7 (6)
O2—Cd1—O1—C10.6 (2)C15—C16—C17—C25179.5 (4)
O3—Cd1—O2—C1−27.6 (4)C16—C17—C18—C190.2 (6)
O1W—Cd1—O2—C1−114.0 (3)C25—C17—C18—C19−180.0 (4)
N2—Cd1—O2—C193.8 (3)C15—N2—C19—C180.4 (6)
N1—Cd1—O2—C1159.0 (3)Cd1—N2—C19—C18−171.2 (3)
O1—Cd1—O2—C1−0.6 (2)C15—N2—C19—C20179.9 (4)
O1W—Cd1—O3—C822.1 (7)Cd1—N2—C19—C208.3 (4)
N2—Cd1—O3—C8−177.0 (7)C17—C18—C19—N2−0.1 (6)
N1—Cd1—O3—C8111.8 (7)C17—C18—C19—C20−179.5 (4)
O1—Cd1—O3—C8−84.2 (7)C24—N1—C20—C21−1.3 (6)
O2—Cd1—O3—C8−62.3 (8)Cd1—N1—C20—C21179.0 (3)
Cd1—O2—C1—O11.1 (4)C24—N1—C20—C19178.2 (4)
Cd1—O2—C1—C2−177.5 (4)Cd1—N1—C20—C19−1.4 (5)
Cd1—O1—C1—O2−1.1 (4)N2—C19—C20—N1−4.5 (5)
Cd1—O1—C1—C2177.5 (3)C18—C19—C20—N1175.0 (4)
O2—C1—C2—C3151.3 (4)N2—C19—C20—C21175.0 (4)
O1—C1—C2—C3−27.4 (6)C18—C19—C20—C21−5.5 (6)
O2—C1—C2—C7−29.9 (7)N1—C20—C21—C220.8 (6)
O1—C1—C2—C7151.5 (4)C19—C20—C21—C22−178.7 (4)
C7—C2—C3—C42.4 (8)C20—C21—C22—C231.0 (7)
C1—C2—C3—C4−178.7 (5)C20—C21—C22—C26−179.8 (4)
C2—C3—C4—C5−3.3 (8)C21—C22—C23—C24−2.1 (7)
C3—C4—C5—C62.4 (9)C26—C22—C23—C24178.6 (5)
C4—C5—C6—C7−0.7 (9)C20—N1—C24—C230.1 (7)
C5—C6—C7—C2−0.1 (8)Cd1—N1—C24—C23179.7 (4)
C5—C6—C7—C7i176.7 (5)C22—C23—C24—N11.7 (8)
C3—C2—C7—C6−0.7 (7)
Symmetry codes: (i) −x, y, −z+1/2.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1W—H1WB···O4i0.851.782.632 (4)174
O1W—H1WA···O1i0.851.952.782 (4)164
Symmetry codes: (i) −x, y, −z+1/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1W—H1WB···O4i0.851.782.632 (4)174
O1W—H1WA···O1i0.851.952.782 (4)164
Symmetry codes: (i) −x, y, −z+1/2.
references
References top

Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.

Jiang, M.-X. & Feng, Y.-L. (2009). Acta Cryst. E65, m654.

Li, F., Zeng, H., Yan, Z. & Li, T. (2009). Acta Cryst. E65, m681.

Rizal, M. R. & Ng, S. W. (2009). Acta Cryst. E65, m1178.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Xu, B.-Y., Xie, T., Lu, S.-J., Xue, B. & Li, W. (2009). Acta Cryst. E65, m856–m857.

Zhang, L. (2009). Acta Cryst. E65, m871–m872.

Zhang, J., Chen, X.-D., Zhang, H.-H. & Sun, B.-W. (2009). Acta Cryst. E65, m1136.