PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2008 July 1; 64(Pt 7): m937.
Published online 2008 June 19. doi:  10.1107/S1600536808018126
PMCID: PMC2961672

Bis(2,5-dihydroxy­benzoato-κO)bis­(1,10-phenathroline-κ2 N,N′)cadmium(II) 1.25-hydrate

Abstract

In the crystal structure of the title compound, [Cd(C7H5O4)2(C12H8N2)2]·1.25H2O, the Cd2+ cation is coordinated by two phenanthroline (phen) mol­ecules and two 2,5-dihydroxy­benzoate (dhba) anions in a distorted octa­hedral geometry. The centroid–centroid distances of 3.809 (2) and 3.680 (2) Å between nearly parallel pyridine rings of the phen ligands and the benzene rings of dhba anions indicate that the dhba anions are involved in π–π stacking in the crystal structure. The face-to-face separation of 3.35 (3) Å between parallel phen ring systems also suggests π–π stacking between adjacent complex mol­ecules. The crystal structure contains extensive O—H(...)O and C—H(...)O hydrogen bonding.

Related literature

For general background, see: Su & Xu (2004 [triangle]); Li et al. (2005 [triangle]). For a related structure, see: Huang et al. (2006 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0m937-scheme1.jpg

Experimental

Crystal data

  • [Cd(C7H5O4)2(C12H8N2)2]·1.25H2O
  • M r = 801.55
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0m937-efi1.jpg
  • a = 10.8992 (18) Å
  • b = 27.300 (2) Å
  • c = 11.4218 (12) Å
  • β = 93.700 (6)°
  • V = 3391.5 (7) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.71 mm−1
  • T = 295 (2) K
  • 0.20 × 0.16 × 0.12 mm

Data collection

  • Rigaku R-AXIS RAPID IP diffractometer
  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995 [triangle]) T min = 0.875, T max = 0.928
  • 25199 measured reflections
  • 6639 independent reflections
  • 4509 reflections with I > 2σ(I)
  • R int = 0.064

Refinement

  • R[F 2 > 2σ(F 2)] = 0.042
  • wR(F 2) = 0.092
  • S = 1.03
  • 6639 reflections
  • 478 parameters
  • H-atom parameters constrained
  • Δρmax = 0.53 e Å−3
  • Δρmin = −0.51 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 1998 [triangle]); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 [triangle]); program(s) used to solve structure: SIR92 (Altomare et al., 1993 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808018126/rk2092sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808018126/rk2092Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The work was supported by the ZIJIN project of Zhejiang University, China.

supplementary crystallographic information

Comment

As part of investigation on the nature of π-π stacking between aromatic rings (Su & Xu, 2004; Li et al., 2005), the title complex recently has been prepared and its crystal structure is reported here.

The molecular structure of the title compound is shown on Fig. 1. The Cd2+ cation is coordinated by two phenanthroline (phen) ligands and two 2,5-dihydroxybenzoate (dhba) anions with a distorted octahedral geometry. The centroid-to-centroid distance of 3.809 (2)Å between nearly parallel N1-pyridine and C2i-benzene rings (dihedral angle 4.89 (17)°; symmetry code: (i) x-1, y, z) and the centroid-to-centroid distance of 3.680 (2)Å between nearly parallel N4-pyridine and C12ii-benzene rings (dihedral angle 5.33 (11)°; symmetry code: (ii) x, y, z-1) indicate that dhba anions are involved in π-π stacking in the crystal structure (Fig. 2), which agrees with the situation found in the 3,5-dihydroxybenzoate complex of Cu2+ (Huang et al., 2006). The face-to-face separation of 3.35 (3)Å suggests the existence of π-π stacking between parallel C31-phen and C31iii-phen ring systems (Fig. 3) (symmetry code: (iii) -x, 1-y, 1-z). The crystal structure contains extensive O–H···O and C–H···O hydrogen bonding (Table 1).

Experimental

Cd(NO3)2.4H2O (0.31 g, 1 mmol), dhba (0.31 g, 2 mmol), phen (0.36 g, 2 mmol) and Na2CO3 (0.10 g, 1 mmol) were dissolved in a water-ethanol mixture (20 ml, 2:1). The solution was refluxed for 2 h. After cooling to room temperature the solution was filtered. Single crystals of the title compound were obtained from the filtrate after 4 weeks.

Refinement

The site occupancy factor of the O2W water molecule was initially refined and converged to 0.28, and fixed as 0.25 at final cycles of refinemens. Water H atoms were placed in chemical sensible positions and refined in riding mode with Uiso(H) = 1.5Ueq(O). Other H atoms were placed in calculated positions with C–H = 0.93Å and O–H = 0.82Å, and refined in riding mode with Uiso(H) = 1.2Ueq(C) or 1.5UeqU(O).

Figures

Fig. 1.
The molecular structure of the title compound with the numbering scheme. The displacement ellipsoids are drawn at 40% probability level. H atoms are presented as a small spheres of arbitrary radius. Dashed lines indicate hydrogen bonding.
Fig. 2.
A diagram showing π-π stacking between phen and dhba (symmetry codes: (i) x-1, y, z; (ii) x, y, z-1).
Fig. 3.
A diagram showing π-π stacking between phen ligands (symmetry code: (iii) -x, 1-y, 1-z).

Crystal data

[Cd(C7H5O4)2(C12H8N2)2]·1.25H2OF000 = 1626
Mr = 801.55Dx = 1.570 Mg m3
Monoclinic, P21/nMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 6929 reflections
a = 10.8992 (18) Åθ = 2.2–25.5º
b = 27.300 (2) ŵ = 0.71 mm1
c = 11.4218 (12) ÅT = 295 (2) K
β = 93.700 (6)ºPrism, colourless
V = 3391.5 (7) Å30.20 × 0.16 × 0.12 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID IP diffractometer6639 independent reflections
Radiation source: Fine-focus sealed tube4509 reflections with I > 2σ(I)
Monochromator: GraphiteRint = 0.064
Detector resolution: 10.0 pixels mm-1θmax = 26.0º
T = 295(2) Kθmin = 1.5º
ω scansh = −13→13
Absorption correction: multi-scan(ABSCOR; Higashi, 1995)k = −33→31
Tmin = 0.875, Tmax = 0.928l = −8→14
25199 measured reflections

Refinement

Refinement on F2Secondary atom site location: Difmap
Least-squares matrix: FullHydrogen site location: Geom
R[F2 > 2σ(F2)] = 0.042H-atom parameters constrained
wR(F2) = 0.092  w = 1/[σ2(Fo2) + (0.0349P)2] where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
6639 reflectionsΔρmax = 0.53 e Å3
478 parametersΔρmin = −0.51 e Å3
Primary atom site location: DirectExtinction correction: none

Special details

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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)

xyzUiso*/UeqOcc. (<1)
Cd0.27239 (2)0.627675 (9)0.32033 (2)0.03808 (10)
N10.0736 (3)0.61272 (10)0.3827 (3)0.0437 (8)
N20.2176 (3)0.54243 (10)0.2903 (3)0.0426 (7)
N30.2325 (3)0.71386 (10)0.2909 (3)0.0409 (7)
N40.1908 (2)0.64287 (10)0.1245 (3)0.0373 (7)
O10.4520 (2)0.60327 (9)0.2586 (2)0.0554 (7)
O20.5248 (2)0.67858 (9)0.2365 (2)0.0590 (8)
O30.7449 (2)0.69059 (9)0.1815 (2)0.0618 (8)
H3A0.67840.69820.20590.093*
O40.7610 (2)0.49241 (8)0.0835 (2)0.0627 (8)
H4A0.70090.47820.10670.094*
O50.3253 (2)0.65203 (10)0.5037 (2)0.0559 (7)
O60.3497 (3)0.57527 (10)0.5661 (2)0.0674 (8)
O70.4132 (2)0.55776 (9)0.7805 (2)0.0625 (8)
H7A0.39310.55120.71190.094*
O80.3815 (3)0.75593 (9)0.8687 (3)0.0688 (8)
H8A0.35020.77090.81220.103*
O1W0.5601 (4)0.53969 (17)0.4499 (5)0.164 (2)
H1A0.52630.55100.37700.246*
H1B0.51070.55180.50610.246*
O2W0.4794 (19)0.7748 (7)0.1426 (18)0.175 (8)0.25
H2A0.49510.74620.17480.262*0.25
H2B0.44710.76920.07280.262*0.25
C10.5335 (3)0.63324 (14)0.2289 (3)0.0428 (9)
C20.6459 (3)0.61142 (12)0.1815 (3)0.0374 (8)
C30.7463 (3)0.64152 (13)0.1592 (3)0.0438 (9)
C40.8490 (3)0.62084 (14)0.1130 (3)0.0527 (10)
H40.91600.64050.09850.063*
C50.8524 (3)0.57144 (14)0.0885 (3)0.0532 (11)
H50.92170.55810.05730.064*
C60.7541 (3)0.54164 (13)0.1099 (3)0.0451 (9)
C70.6515 (3)0.56179 (12)0.1553 (3)0.0410 (9)
H70.58480.54180.16870.049*
C110.3464 (3)0.62091 (14)0.5830 (4)0.0452 (10)
C120.3709 (3)0.63929 (12)0.7055 (3)0.0379 (9)
C130.4065 (3)0.60753 (13)0.7972 (4)0.0440 (9)
C140.4356 (3)0.62616 (15)0.9088 (4)0.0543 (10)
H140.46070.60500.96950.065*
C150.4274 (3)0.67550 (15)0.9302 (4)0.0535 (10)
H150.44820.68761.00490.064*
C160.3888 (3)0.70707 (13)0.8417 (4)0.0441 (9)
C170.3611 (3)0.68917 (12)0.7302 (3)0.0417 (9)
H170.33540.71070.67050.050*
C210.0050 (3)0.64614 (15)0.4309 (4)0.0552 (11)
H210.03770.67730.44310.066*
C22−0.1138 (4)0.63710 (16)0.4643 (4)0.0647 (12)
H22−0.15920.66190.49680.078*
C23−0.1624 (4)0.59145 (16)0.4486 (4)0.0614 (12)
H23−0.24150.58480.47020.074*
C24−0.0925 (3)0.55470 (14)0.3999 (3)0.0490 (10)
C25−0.1337 (4)0.50485 (16)0.3857 (4)0.0598 (12)
H25−0.21140.49640.40800.072*
C26−0.0631 (4)0.47059 (16)0.3413 (4)0.0586 (11)
H26−0.09310.43880.33290.070*
C270.0583 (4)0.48147 (14)0.3058 (3)0.0491 (10)
C280.1355 (4)0.44647 (14)0.2590 (4)0.0626 (12)
H280.10860.41440.24840.075*
C290.2502 (4)0.45961 (14)0.2292 (4)0.0617 (12)
H290.30220.43680.19780.074*
C300.2876 (4)0.50804 (13)0.2466 (4)0.0552 (11)
H300.36600.51670.22660.066*
C310.1027 (3)0.52963 (13)0.3183 (3)0.0421 (9)
C320.0266 (3)0.56682 (13)0.3680 (3)0.0417 (9)
C330.2558 (3)0.74832 (14)0.3709 (4)0.0526 (10)
H330.28900.73910.44460.063*
C340.2328 (4)0.79784 (15)0.3495 (5)0.0650 (13)
H340.25060.82110.40760.078*
C350.1838 (4)0.81149 (14)0.2419 (5)0.0616 (12)
H350.16770.84440.22610.074*
C360.1574 (3)0.77631 (13)0.1546 (4)0.0465 (10)
C370.1035 (4)0.78818 (15)0.0403 (4)0.0587 (12)
H370.08410.82060.02200.070*
C380.0809 (3)0.75324 (16)−0.0406 (4)0.0614 (12)
H380.04510.7617−0.11390.074*
C390.1107 (3)0.70333 (14)−0.0161 (4)0.0455 (10)
C400.0917 (3)0.66543 (17)−0.0998 (4)0.0591 (11)
H400.05860.6725−0.17500.071*
C410.1219 (3)0.61860 (15)−0.0698 (4)0.0549 (11)
H410.10900.5933−0.12360.066*
C420.1721 (3)0.60929 (15)0.0422 (4)0.0496 (10)
H420.19420.57720.06080.060*
C430.1612 (3)0.69012 (13)0.0952 (3)0.0386 (9)
C440.1847 (3)0.72736 (13)0.1834 (3)0.0386 (9)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cd0.04016 (15)0.03730 (16)0.03675 (18)−0.00085 (12)0.00215 (11)−0.00014 (13)
N10.0454 (17)0.0433 (18)0.043 (2)−0.0004 (14)0.0040 (15)0.0050 (15)
N20.0491 (18)0.0400 (17)0.038 (2)−0.0047 (14)0.0013 (15)0.0008 (15)
N30.0441 (17)0.0397 (18)0.039 (2)−0.0014 (13)0.0033 (15)−0.0020 (16)
N40.0418 (16)0.0407 (17)0.0295 (18)0.0013 (13)0.0030 (14)−0.0008 (15)
O10.0436 (15)0.0530 (16)0.071 (2)0.0009 (12)0.0142 (14)0.0005 (14)
O20.0641 (17)0.0426 (16)0.071 (2)0.0051 (13)0.0099 (15)−0.0185 (14)
O30.0644 (18)0.0385 (15)0.083 (2)−0.0101 (12)0.0099 (16)−0.0104 (14)
O40.0762 (19)0.0411 (16)0.073 (2)0.0051 (13)0.0205 (16)−0.0073 (14)
O50.0759 (19)0.0534 (17)0.0372 (17)−0.0074 (14)−0.0060 (14)0.0017 (14)
O60.101 (2)0.0471 (17)0.055 (2)−0.0132 (15)0.0091 (17)−0.0127 (15)
O70.083 (2)0.0428 (16)0.062 (2)0.0002 (14)0.0042 (16)0.0066 (14)
O80.092 (2)0.0461 (17)0.067 (2)−0.0010 (15)−0.0033 (17)−0.0163 (15)
O1W0.106 (3)0.200 (5)0.191 (5)0.021 (3)0.043 (3)0.052 (4)
O2W0.22 (2)0.158 (17)0.144 (19)0.026 (15)−0.026 (16)0.012 (14)
C10.042 (2)0.049 (2)0.037 (2)0.0022 (18)−0.0025 (17)−0.0046 (19)
C20.0400 (19)0.037 (2)0.035 (2)0.0011 (15)0.0003 (17)0.0003 (17)
C30.050 (2)0.041 (2)0.040 (3)−0.0044 (16)0.0013 (19)0.0014 (17)
C40.047 (2)0.054 (3)0.058 (3)−0.0085 (18)0.012 (2)0.009 (2)
C50.049 (2)0.060 (3)0.052 (3)0.0049 (19)0.014 (2)0.001 (2)
C60.058 (2)0.040 (2)0.037 (2)0.0063 (18)0.0031 (19)−0.0011 (18)
C70.042 (2)0.039 (2)0.042 (2)−0.0003 (16)0.0018 (18)0.0032 (17)
C110.043 (2)0.049 (3)0.044 (3)−0.0119 (17)0.0054 (18)−0.008 (2)
C120.0353 (19)0.043 (2)0.036 (2)−0.0043 (15)0.0035 (16)0.0005 (17)
C130.048 (2)0.039 (2)0.046 (3)−0.0022 (17)0.0075 (19)0.005 (2)
C140.057 (2)0.060 (3)0.046 (3)−0.005 (2)−0.003 (2)0.014 (2)
C150.057 (2)0.067 (3)0.036 (3)−0.009 (2)0.002 (2)−0.005 (2)
C160.048 (2)0.045 (2)0.039 (3)−0.0036 (17)0.0025 (19)−0.005 (2)
C170.044 (2)0.037 (2)0.043 (3)0.0012 (16)0.0008 (18)0.0035 (18)
C210.053 (2)0.052 (2)0.061 (3)0.0064 (19)0.010 (2)0.006 (2)
C220.058 (3)0.065 (3)0.073 (3)0.017 (2)0.017 (2)0.014 (2)
C230.045 (2)0.083 (3)0.057 (3)0.010 (2)0.012 (2)0.024 (3)
C240.043 (2)0.066 (3)0.038 (2)−0.0071 (19)−0.0060 (19)0.017 (2)
C250.049 (2)0.080 (3)0.049 (3)−0.023 (2)−0.007 (2)0.020 (2)
C260.066 (3)0.059 (3)0.050 (3)−0.027 (2)−0.008 (2)0.010 (2)
C270.063 (3)0.046 (2)0.036 (2)−0.0118 (19)−0.008 (2)0.0047 (19)
C280.087 (3)0.043 (2)0.057 (3)−0.012 (2)−0.006 (3)−0.001 (2)
C290.073 (3)0.042 (2)0.070 (3)0.001 (2)0.006 (2)−0.007 (2)
C300.058 (2)0.046 (2)0.062 (3)−0.0027 (19)0.010 (2)0.000 (2)
C310.049 (2)0.044 (2)0.032 (2)−0.0084 (17)−0.0033 (18)0.0103 (18)
C320.042 (2)0.054 (2)0.029 (2)−0.0024 (17)−0.0011 (17)0.0100 (18)
C330.055 (2)0.048 (2)0.055 (3)−0.0009 (19)0.001 (2)−0.010 (2)
C340.069 (3)0.045 (3)0.081 (4)0.000 (2)0.005 (3)−0.019 (3)
C350.054 (3)0.036 (2)0.095 (4)0.0041 (18)0.009 (3)0.001 (3)
C360.036 (2)0.043 (2)0.061 (3)0.0022 (17)0.011 (2)0.004 (2)
C370.050 (2)0.049 (3)0.078 (4)0.0118 (19)0.011 (2)0.021 (3)
C380.051 (2)0.076 (3)0.058 (3)0.010 (2)0.006 (2)0.030 (3)
C390.038 (2)0.058 (3)0.041 (3)0.0046 (17)0.0042 (18)0.012 (2)
C400.051 (2)0.088 (3)0.039 (3)−0.001 (2)0.000 (2)0.002 (3)
C410.054 (2)0.070 (3)0.041 (3)−0.002 (2)0.003 (2)−0.010 (2)
C420.047 (2)0.059 (3)0.044 (3)0.0043 (19)0.006 (2)−0.002 (2)
C430.0302 (18)0.045 (2)0.041 (2)0.0007 (15)0.0055 (17)0.0082 (19)
C440.0310 (18)0.043 (2)0.043 (3)0.0016 (15)0.0098 (17)0.0058 (19)

Geometric parameters (Å, °)

Cd—O12.225 (2)C14—H140.9300
Cd—O52.237 (3)C15—C161.374 (5)
Cd—N12.360 (3)C15—H150.9300
Cd—N42.389 (3)C16—C171.379 (5)
Cd—N32.412 (3)C17—H170.9300
Cd—N22.422 (3)C21—C221.396 (5)
N1—C211.322 (4)C21—H210.9300
N1—C321.360 (4)C22—C231.361 (5)
N2—C301.327 (4)C22—H220.9300
N2—C311.358 (4)C23—C241.397 (5)
N3—C331.325 (4)C23—H230.9300
N3—C441.353 (4)C24—C321.410 (5)
N4—C421.319 (4)C24—C251.439 (5)
N4—C431.366 (4)C25—C261.332 (5)
O1—C11.270 (4)C25—H250.9300
O2—C11.245 (4)C26—C271.440 (5)
O3—C31.364 (4)C26—H260.9300
O3—H3A0.8200C27—C281.402 (5)
O4—C61.380 (4)C27—C311.405 (5)
O4—H4A0.8200C28—C291.364 (5)
O5—C111.252 (4)C28—H280.9300
O6—C111.262 (4)C29—C301.394 (5)
O7—C131.375 (4)C29—H290.9300
O7—H7A0.8200C30—H300.9300
O8—C161.373 (4)C31—C321.450 (5)
O8—H8A0.8200C33—C341.394 (5)
O1W—H1A0.9410C33—H330.9300
O1W—H1B0.9244C34—C351.360 (6)
O2W—H2A0.8772C34—H340.9300
O2W—H2B0.8639C35—C361.400 (5)
C1—C21.495 (5)C35—H350.9300
C2—C71.390 (4)C36—C441.404 (5)
C2—C31.405 (5)C36—C371.434 (6)
C3—C41.387 (5)C37—C381.339 (6)
C4—C51.378 (5)C37—H370.9300
C4—H40.9300C38—C391.424 (5)
C5—C61.380 (5)C38—H380.9300
C5—H50.9300C39—C431.399 (5)
C6—C71.377 (5)C39—C401.414 (5)
C7—H70.9300C40—C411.358 (5)
C11—C121.494 (5)C40—H400.9300
C12—C171.396 (4)C41—C421.383 (5)
C12—C131.395 (5)C41—H410.9300
C13—C141.390 (5)C42—H420.9300
C14—C151.373 (5)C43—C441.443 (5)
O1—Cd—O5101.93 (10)C16—C17—H17119.4
O1—Cd—N1152.57 (10)C12—C17—H17119.4
O5—Cd—N187.41 (10)N1—C21—C22123.5 (4)
O1—Cd—N492.14 (10)N1—C21—H21118.3
O5—Cd—N4151.96 (10)C22—C21—H21118.3
N1—Cd—N491.11 (10)C23—C22—C21119.0 (4)
O1—Cd—N3113.72 (9)C23—C22—H22120.5
O5—Cd—N382.76 (10)C21—C22—H22120.5
N1—Cd—N392.88 (9)C22—C23—C24119.5 (4)
N4—Cd—N369.34 (10)C22—C23—H23120.2
O1—Cd—N283.18 (9)C24—C23—H23120.2
O5—Cd—N2117.68 (10)C23—C24—C32118.0 (4)
N1—Cd—N269.74 (10)C23—C24—C25123.4 (4)
N4—Cd—N287.76 (10)C32—C24—C25118.6 (4)
N3—Cd—N2151.29 (10)C26—C25—C24121.6 (4)
C21—N1—C32118.0 (3)C26—C25—H25119.2
C21—N1—Cd124.1 (3)C24—C25—H25119.2
C32—N1—Cd117.9 (2)C25—C26—C27121.7 (4)
C30—N2—C31117.9 (3)C25—C26—H26119.1
C30—N2—Cd126.2 (2)C27—C26—H26119.1
C31—N2—Cd115.9 (2)C28—C27—C31117.7 (4)
C33—N3—C44118.5 (3)C28—C27—C26123.5 (4)
C33—N3—Cd124.9 (3)C31—C27—C26118.8 (4)
C44—N3—Cd116.6 (2)C29—C28—C27119.9 (4)
C42—N4—C43117.3 (3)C29—C28—H28120.1
C42—N4—Cd125.3 (3)C27—C28—H28120.1
C43—N4—Cd117.5 (2)C28—C29—C30118.5 (4)
C1—O1—Cd122.5 (2)C28—C29—H29120.7
C3—O3—H3A109.5C30—C29—H29120.7
C6—O4—H4A109.5N2—C30—C29123.7 (4)
C11—O5—Cd120.0 (2)N2—C30—H30118.2
C13—O7—H7A109.5C29—C30—H30118.2
C16—O8—H8A109.5N2—C31—C27122.3 (3)
H1A—O1W—H1B106.5N2—C31—C32118.1 (3)
H2A—O2W—H2B106.5C27—C31—C32119.5 (3)
O2—C1—O1124.3 (3)N1—C32—C24122.0 (3)
O2—C1—C2119.3 (3)N1—C32—C31118.3 (3)
O1—C1—C2116.3 (3)C24—C32—C31119.8 (3)
C7—C2—C3119.0 (3)N3—C33—C34122.9 (4)
C7—C2—C1121.0 (3)N3—C33—H33118.5
C3—C2—C1119.9 (3)C34—C33—H33118.5
O3—C3—C4119.3 (3)C35—C34—C33118.7 (4)
O3—C3—C2121.5 (3)C35—C34—H34120.7
C4—C3—C2119.2 (3)C33—C34—H34120.7
C5—C4—C3120.6 (3)C34—C35—C36120.4 (4)
C5—C4—H4119.7C34—C35—H35119.8
C3—C4—H4119.7C36—C35—H35119.8
C4—C5—C6120.6 (3)C35—C36—C44117.1 (4)
C4—C5—H5119.7C35—C36—C37123.1 (4)
C6—C5—H5119.7C44—C36—C37119.8 (4)
C7—C6—C5119.3 (3)C38—C37—C36120.9 (4)
C7—C6—O4121.9 (3)C38—C37—H37119.6
C5—C6—O4118.8 (3)C36—C37—H37119.6
C6—C7—C2121.2 (3)C37—C38—C39121.1 (4)
C6—C7—H7119.4C37—C38—H38119.4
C2—C7—H7119.4C39—C38—H38119.4
O5—C11—O6124.4 (4)C43—C39—C40117.2 (4)
O5—C11—C12117.6 (3)C43—C39—C38119.7 (4)
O6—C11—C12118.0 (4)C40—C39—C38123.1 (4)
C17—C12—C13118.4 (3)C41—C40—C39119.7 (4)
C17—C12—C11120.4 (3)C41—C40—H40120.2
C13—C12—C11121.2 (3)C39—C40—H40120.2
O7—C13—C14118.5 (4)C40—C41—C42118.8 (4)
O7—C13—C12121.7 (4)C40—C41—H41120.6
C14—C13—C12119.8 (3)C42—C41—H41120.6
C15—C14—C13120.6 (4)N4—C42—C41124.4 (4)
C15—C14—H14119.7N4—C42—H42117.8
C13—C14—H14119.7C41—C42—H42117.8
C14—C15—C16120.3 (4)N4—C43—C39122.6 (3)
C14—C15—H15119.8N4—C43—C44117.7 (3)
C16—C15—H15119.8C39—C43—C44119.7 (3)
C15—C16—O8117.6 (4)N3—C44—C36122.4 (3)
C15—C16—C17119.7 (4)N3—C44—C43118.8 (3)
O8—C16—C17122.7 (4)C36—C44—C43118.8 (4)
C16—C17—C12121.2 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1W—H1A···O10.942.092.974 (6)155
O1W—H1B···O60.922.032.892 (6)155
O2W—H2A···O20.881.992.869 (18)175
O2W—H2B···O8i0.862.423.28 (2)173
O3—H3A···O20.821.812.540 (3)147
O4—H4A···O7ii0.822.092.877 (3)160
O7—H7A···O60.821.822.546 (3)147
O8—H8A···O3iii0.822.102.917 (4)171
C23—H23···O1Wiv0.932.493.339 (6)153
C25—H25···O6v0.932.503.285 (5)143
C30—H30···O10.932.563.155 (5)122
C33—H33···O50.932.503.105 (5)123
C38—H38···O2vi0.932.363.182 (5)147
C42—H42···O4vii0.932.583.231 (5)127

Symmetry codes: (i) x, y, z−1; (ii) −x+1, −y+1, −z+1; (iii) x−1/2, −y+3/2, z+1/2; (iv) x−1, y, z; (v) −x, −y+1, −z+1; (vi) x−1/2, −y+3/2, z−1/2; (vii) −x+1, −y+1, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RK2092).

References

  • Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst.26, 343–350.
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Farrugia, L. J. (1999). J. Appl. Cryst.32, 837–838.
  • Higashi, T. (1995). ABSCOR Rigaku Corporation, Tokyo, Japan.
  • Huang, X., Xiao, L.-P. & Xu, D.-J. (2006). Acta Cryst. E62, m2246–m2248.
  • Li, H., Liu, J.-G. & Xu, D.-J. (2005). Acta Cryst. E61, m761–m763.
  • Rigaku (1998). PROCESS-AUTO Rigaku Corporation, Tokyo, Japan.
  • Rigaku/MSC (2002). CrystalStructure Rigaku/MSC, The Woodlands, Texas, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Su, J.-R. & Xu, D.-J. (2004). J. Coord. Chem.57, 223–229.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography