PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2009 August 1; 65(Pt 8): m885–m886.
Published online 2009 July 8. doi:  10.1107/S1600536809024246
PMCID: PMC2977095

catena-Poly[[bis­[4-(1H-imidazo[4,5-f][1,10]phenanthrolin-2-yl)phenol]cadmium(II)]-μ-fumarato]

Abstract

In the polymeric title compound, [Cd(C4H2O4)(C19H12N4O)2]n, the CdII centre is eight-coordinated within an N4O4 donor set derived from two chelating 4-(1H-imidazo[4,5-f][1,10]phenanthrolin-2-yl)phenol ligands and two asymmetrically chelating carboxyl­ate residues of bridging fumarate dianions. The linear chains are linked into a layer in the ac plane via O—H(...)Ocarboxyl­ate hydrogen bonds. Layers are connected into double layers via N—H(...)Ocarboxyl­ate hydrogen bonds and these stack along the b axis. C—H(...)π inter­actions are also present. Disorder in the ethyl­ene portion of the fumarate was modelled over two positions, the major component having a site-occupancy factor of 0.677 (15).

Related literature

For general background and related structures see: Chen & Liu (2002 [triangle]); Yang et al. (2007a [triangle],b [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0m885-scheme1.jpg

Experimental

Crystal data

  • [Cd(C4H2O4)(C19H12N4O)2]
  • M r = 851.11
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0m885-efi1.jpg
  • a = 9.5596 (3) Å
  • b = 13.5628 (7) Å
  • c = 15.8934 (16) Å
  • α = 64.756 (3)°
  • β = 77.142 (1)°
  • γ = 72.929 (4)°
  • V = 1770.4 (2) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.68 mm−1
  • T = 293 K
  • 0.33 × 0.25 × 0.20 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.654, T max = 0.772 (expected range = 0.739–0.873)
  • 15185 measured reflections
  • 7170 independent reflections
  • 5600 reflections with I > 2σ(I)
  • R int = 0.028

Refinement

  • R[F 2 > 2σ(F 2)] = 0.043
  • wR(F 2) = 0.119
  • S = 1.05
  • 7170 reflections
  • 529 parameters
  • 2 restraints
  • H-atom parameters constrained
  • Δρmax = 1.67 e Å−3
  • Δρmin = −0.30 e Å−3

Data collection: SMART (Bruker, 1997 [triangle]); cell refinement: SAINT (Bruker, 1999 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: DIAMOND (Brandenburg, 2006 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809024246/lh2849sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809024246/lh2849Isup2.hkl

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

Acknowledgments

The authors thank Beihua University for supporting this work.

supplementary crystallographic information

Comment

The chelating molecules 1,10-phenanthroline and 2,2'-bipyridyl have been widely used to build supramolecular architectures owing to their excellent coordinating ability and large conjugated system (Chen & Liu, 2002). However, far less attention has been given to their derivatives (Yang et al., 2007a; Yang et al., 2007b). For example, the rare phenanthroline derivative 4-(1H-imidazo[4,5-f][1,10]phenanthrolin-2-yl)phenol (L) possesses varied aromatic systems, and is a good candidate for the construction of metal-organic supramolecular architectures. In this contribution, a cadmium coordination polymer containing L and fumarate has been synthesized, namely [CdL2(C4H2O4)]n (I), and its crystal structure determined.

The asymmetric unit of (I) comprises cadmium, two chelating L ligands and a bridging fumarate dianion, Fig. 1. The Cd–N bond distances lie in the narrow range 2.320 (3) to 2.351 (3) Å and, reflecting the asymmetric mode of coordination exhibited by the carboxylate residues, the Cd–O distances range from 2.496 (3) to 2.742 (3) Å. The cadmium centre is eight-coordinate within an N4O4 donor set. The polymeric chain is linear, Fig. 2, and these form a layer in the ac plane with adjacent chains being connected by O–H···O hydrogen bonds, Table 1. Centrosymmetrically related layers associate via N—H···O hydrogen bonds to form a double layer and these aggregates stack along the b axis, Fig. 3. Further consolidation to the crystal packing is afforded by C–H···O interactions that occur within layers and between double layers, and by C–H···π contacts within double layers, Table 1.

Experimental

A mixture of fumeric acid (0.5 mmol), [4-(1H-imidazo[4,5-f][1,10]phenanthrolin-2-yl)phenol] (0.5 mmol), NaOH (1 mmol) and CdCl2.2H2O (0.5 mmol) was suspended in deionized water (12 ml) and sealed in a 20-ml Teflon-lined autoclave. Upon heating at 433 K for one week, the autoclave was slowly cooled to room temperature. The crystals were collected, washed with deionized water, and dried.

Refinement

Carbon-bound H-atoms were placed in calculated positions with C—H = 0.93 Å, and were included in the refinement in the riding model approximation, with U(H) set to 1.2Ueq(C). The O—H and N—H atoms were located from a difference map but included in their idealized positions with O—H = 0.84 Å and U(H) set to 1.5Ueq(O) and N—H = 0.86 Å and U(H) set to 1.2Ueq(N).

Disorder was noted in the positions of the ethylene atoms of the fumarate dianion. The atoms were modelled over two positions with the major component (anisotropic displacement parameters) having a site occupancy = 0.677 (15).

The maximum and minimum residual electron density peaks of 1.67 and 0.30 e Å-3, respectively, were located 1.37 Å and 1.53 Å from the H21 and N2 atoms, respectively.

Figures

Fig. 1.
The asymmetric unit in the polymeric structure of (I), showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 70% probability level. Only the major component of the disordered ethylene residue in the fumarate dianion is shown.
Fig. 2.
View of links mediated by O—H···O hydrogen bonding (dashed lines) between the polymeric chains in (I).
Fig. 3.
View of the double layers mediated by N—H···O hydrogen bonding (dashed lines) and the stacking of these in the crystal structure of (I).

Crystal data

[Cd(C4H2O4)(C19H12N4O)2]Z = 2
Mr = 851.11F(000) = 860
Triclinic, P1Dx = 1.597 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.5596 (3) ÅCell parameters from 7163 reflections
b = 13.5628 (7) Åθ = 3.0–26.4°
c = 15.8934 (16) ŵ = 0.68 mm1
α = 64.756 (3)°T = 293 K
β = 77.142 (1)°Block, pale-yellow
γ = 72.929 (4)°0.33 × 0.25 × 0.20 mm
V = 1770.4 (2) Å3

Data collection

Bruker SMART APEX diffractometer7170 independent reflections
Radiation source: fine-focus sealed tube5600 reflections with I > 2σ(I)
graphiteRint = 0.028
[var phi] and ω scansθmax = 26.4°, θmin = 4.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −8→11
Tmin = 0.654, Tmax = 0.772k = −16→16
15185 measured reflectionsl = −19→19

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119H-atom parameters constrained
S = 1.05w = 1/[σ2(Fo2) + (0.0737P)2 + 0.2724P] where P = (Fo2 + 2Fc2)/3
7170 reflections(Δ/σ)max = 0.002
529 parametersΔρmax = 1.67 e Å3
2 restraintsΔρmin = −0.30 e Å3

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 > 2σ(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)
Cd0.70820 (3)0.16101 (2)0.698014 (15)0.03567 (11)
O10.3239 (4)0.3694 (3)1.4609 (2)0.0702 (9)
H1O0.35200.32091.51220.105*
O20.9918 (4)0.3606 (3)−0.19919 (18)0.0599 (8)
H2O0.97450.3150−0.21610.090*
O30.9693 (3)0.0674 (3)0.72834 (19)0.0504 (7)
O40.9168 (3)0.2304 (3)0.73968 (19)0.0488 (7)
O51.4906 (4)0.0739 (4)0.7290 (2)0.0762 (11)
O61.4676 (3)0.2372 (3)0.6096 (2)0.0619 (8)
N10.6857 (3)0.0720 (3)0.85992 (19)0.0357 (7)
N20.5641 (3)0.2916 (3)0.7615 (2)0.0412 (7)
N30.5178 (4)0.1543 (3)1.1456 (2)0.0439 (8)
H3n0.54370.09301.19240.053*
N40.4233 (4)0.3334 (3)1.0646 (2)0.0534 (9)
N50.7763 (3)0.0688 (3)0.59460 (18)0.0334 (6)
N60.7974 (3)0.2817 (3)0.55281 (19)0.0351 (7)
N70.9021 (3)0.1514 (3)0.25644 (19)0.0374 (7)
H7n0.90450.09200.24850.045*
N80.9143 (4)0.3264 (3)0.2216 (2)0.0436 (8)
C10.7408 (4)−0.0355 (4)0.9060 (3)0.0430 (9)
H10.7878−0.07930.87150.052*
C20.7323 (4)−0.0867 (4)1.0031 (3)0.0479 (10)
H20.7702−0.16301.03300.057*
C30.6669 (4)−0.0216 (4)1.0534 (3)0.0449 (9)
H30.6608−0.05351.11840.054*
C40.6091 (4)0.0922 (3)1.0077 (2)0.0370 (8)
C50.6194 (4)0.1374 (3)0.9086 (2)0.0352 (8)
C60.5558 (4)0.2550 (3)0.8563 (2)0.0377 (8)
C70.5027 (5)0.3966 (4)0.7136 (3)0.0533 (11)
H70.50640.42090.64900.064*
C80.4318 (5)0.4735 (4)0.7559 (3)0.0594 (12)
H80.39120.54750.71990.071*
C90.4238 (5)0.4376 (4)0.8498 (3)0.0589 (11)
H90.37770.48710.87910.071*
C100.4844 (4)0.3266 (3)0.9028 (3)0.0452 (9)
C110.4802 (4)0.2799 (4)1.0036 (3)0.0446 (9)
C120.5385 (4)0.1685 (3)1.0519 (2)0.0406 (9)
C130.4509 (5)0.2526 (4)1.1486 (2)0.0449 (9)
C140.4123 (5)0.2773 (4)1.2344 (3)0.0459 (9)
C150.4932 (4)0.2150 (4)1.3098 (3)0.0470 (9)
H150.56770.15331.30880.056*
C160.4644 (4)0.2436 (4)1.3870 (3)0.0472 (10)
H160.51870.20081.43760.057*
C170.3548 (5)0.3359 (4)1.3886 (3)0.0470 (10)
C180.2717 (5)0.3975 (4)1.3140 (3)0.0552 (11)
H180.19580.45821.31570.066*
C190.3014 (5)0.3691 (4)1.2375 (3)0.0553 (11)
H190.24650.41191.18710.066*
C200.7710 (4)−0.0362 (3)0.6174 (2)0.0416 (9)
H200.7461−0.07920.67990.050*
C210.8009 (5)−0.0851 (3)0.5527 (3)0.0452 (9)
H210.7968−0.15930.57160.054*
C220.8361 (4)−0.0228 (3)0.4611 (3)0.0401 (8)
H220.8560−0.05410.41660.048*
C230.8426 (4)0.0893 (3)0.4337 (2)0.0333 (8)
C240.8130 (3)0.1325 (3)0.5043 (2)0.0297 (7)
C250.8232 (4)0.2460 (3)0.4814 (2)0.0299 (7)
C260.8130 (5)0.3828 (3)0.5334 (3)0.0455 (9)
H260.79590.40680.58230.055*
C270.8534 (5)0.4553 (4)0.4441 (3)0.0530 (11)
H270.86490.52540.43410.064*
C280.8762 (5)0.4227 (3)0.3711 (3)0.0466 (10)
H280.90100.47090.31040.056*
C290.8617 (4)0.3158 (3)0.3888 (2)0.0357 (8)
C300.8838 (4)0.2720 (3)0.3175 (2)0.0363 (8)
C310.8756 (4)0.1642 (3)0.3405 (2)0.0327 (7)
C320.9234 (4)0.2507 (3)0.1887 (2)0.0392 (8)
C330.9472 (4)0.2732 (3)0.0876 (2)0.0404 (8)
C341.0177 (5)0.3571 (3)0.0255 (3)0.0502 (10)
H341.05580.39530.04840.060*
C351.0324 (5)0.3849 (3)−0.0700 (3)0.0504 (10)
H351.08100.4408−0.11080.060*
C360.9748 (5)0.3292 (3)−0.1050 (2)0.0426 (9)
C370.9070 (5)0.2434 (4)−0.0443 (3)0.0491 (10)
H370.87070.2045−0.06750.059*
C380.8935 (5)0.2154 (4)0.0518 (3)0.0488 (10)
H380.84810.15750.09260.059*
C391.0066 (4)0.1455 (4)0.7328 (2)0.0430 (9)0.677 (15)
C401.1717 (6)0.1176 (6)0.7339 (4)0.0345 (18)0.677 (15)
H401.21800.04880.77540.041*0.677 (15)
C411.2483 (6)0.1893 (7)0.6774 (4)0.046 (2)0.677 (15)
H411.20010.26020.64000.055*0.677 (15)
C421.4171 (4)0.1601 (5)0.6706 (3)0.0618 (14)0.677 (15)
C39'1.0066 (4)0.1455 (4)0.7328 (2)0.0430 (9)0.323 (15)
C40'1.1567 (17)0.1868 (16)0.7021 (10)0.039 (4)*0.323 (15)
H40'1.16110.25890.69130.047*0.323 (15)
C41'1.2730 (13)0.1107 (13)0.6934 (8)0.032 (4)*0.323 (15)
H41'1.27270.03950.69940.038*0.323 (15)
C42'1.4171 (4)0.1601 (5)0.6706 (3)0.0618 (14)0.323 (15)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cd0.03240 (15)0.0554 (2)0.02243 (14)−0.01454 (12)0.00236 (9)−0.01769 (12)
O10.094 (3)0.069 (2)0.0517 (18)0.0083 (19)−0.0146 (17)−0.0412 (17)
O20.104 (3)0.0573 (19)0.0251 (13)−0.0357 (18)−0.0051 (14)−0.0116 (13)
O30.0423 (15)0.0675 (19)0.0559 (17)−0.0073 (14)−0.0044 (12)−0.0412 (15)
O40.0499 (16)0.0595 (18)0.0457 (15)−0.0180 (15)−0.0034 (12)−0.0257 (14)
O50.0559 (19)0.134 (3)0.0345 (15)−0.045 (2)0.0013 (14)−0.0170 (18)
O60.0412 (16)0.097 (3)0.0581 (19)−0.0181 (17)−0.0007 (14)−0.0404 (19)
N10.0287 (14)0.051 (2)0.0278 (14)−0.0112 (14)0.0026 (11)−0.0169 (14)
N20.0344 (16)0.055 (2)0.0274 (14)−0.0065 (15)−0.0044 (12)−0.0113 (14)
N30.0433 (18)0.056 (2)0.0266 (15)−0.0088 (16)−0.0011 (13)−0.0139 (15)
N40.062 (2)0.059 (2)0.0395 (18)−0.0094 (18)−0.0001 (16)−0.0244 (17)
N50.0328 (15)0.0449 (18)0.0254 (13)−0.0170 (14)0.0011 (11)−0.0129 (13)
N60.0369 (16)0.0431 (18)0.0307 (14)−0.0094 (14)0.0013 (12)−0.0214 (13)
N70.0479 (18)0.0415 (18)0.0276 (14)−0.0150 (15)0.0007 (12)−0.0170 (13)
N80.063 (2)0.0420 (18)0.0276 (15)−0.0128 (16)−0.0039 (14)−0.0150 (14)
C10.038 (2)0.053 (3)0.0369 (19)−0.0070 (18)0.0016 (16)−0.0211 (18)
C20.042 (2)0.048 (2)0.043 (2)−0.0046 (18)−0.0047 (17)−0.0121 (19)
C30.040 (2)0.060 (3)0.0297 (18)−0.0102 (19)−0.0070 (15)−0.0112 (18)
C40.0298 (17)0.054 (2)0.0289 (17)−0.0135 (17)0.0011 (14)−0.0170 (17)
C50.0271 (16)0.052 (2)0.0261 (16)−0.0117 (16)0.0003 (13)−0.0147 (16)
C60.0301 (17)0.056 (2)0.0286 (17)−0.0101 (17)0.0010 (14)−0.0192 (17)
C70.046 (2)0.065 (3)0.034 (2)−0.006 (2)−0.0034 (17)−0.011 (2)
C80.058 (3)0.052 (3)0.048 (2)−0.001 (2)−0.010 (2)−0.006 (2)
C90.060 (3)0.059 (3)0.052 (2)−0.005 (2)0.000 (2)−0.025 (2)
C100.042 (2)0.052 (3)0.0361 (19)−0.0093 (19)−0.0005 (16)−0.0153 (18)
C110.045 (2)0.058 (3)0.0343 (19)−0.0095 (19)0.0024 (16)−0.0259 (19)
C120.0386 (19)0.055 (3)0.0274 (17)−0.0103 (18)−0.0016 (14)−0.0160 (17)
C130.051 (2)0.063 (3)0.0290 (18)−0.018 (2)0.0058 (16)−0.0267 (18)
C140.050 (2)0.058 (3)0.0347 (19)−0.015 (2)0.0026 (16)−0.0234 (18)
C150.043 (2)0.057 (3)0.045 (2)−0.0060 (19)0.0002 (17)−0.029 (2)
C160.042 (2)0.066 (3)0.038 (2)−0.010 (2)−0.0048 (16)−0.026 (2)
C170.052 (2)0.058 (3)0.041 (2)−0.013 (2)−0.0018 (17)−0.0294 (19)
C180.061 (3)0.057 (3)0.050 (2)0.001 (2)−0.006 (2)−0.032 (2)
C190.060 (3)0.061 (3)0.040 (2)−0.002 (2)−0.0129 (19)−0.018 (2)
C200.047 (2)0.049 (2)0.0297 (17)−0.0233 (19)0.0057 (15)−0.0120 (17)
C210.052 (2)0.041 (2)0.048 (2)−0.0234 (19)0.0017 (18)−0.0165 (18)
C220.044 (2)0.045 (2)0.0398 (19)−0.0158 (18)0.0015 (16)−0.0243 (17)
C230.0296 (17)0.043 (2)0.0311 (17)−0.0100 (16)−0.0006 (13)−0.0185 (16)
C240.0243 (15)0.041 (2)0.0270 (15)−0.0100 (15)−0.0012 (12)−0.0150 (15)
C250.0292 (16)0.0350 (19)0.0271 (16)−0.0054 (15)−0.0002 (13)−0.0161 (14)
C260.060 (3)0.047 (2)0.0369 (19)−0.016 (2)0.0046 (17)−0.0255 (18)
C270.081 (3)0.039 (2)0.043 (2)−0.022 (2)0.006 (2)−0.0197 (18)
C280.066 (3)0.039 (2)0.0327 (19)−0.016 (2)0.0041 (17)−0.0131 (17)
C290.041 (2)0.038 (2)0.0288 (17)−0.0103 (16)0.0004 (14)−0.0150 (15)
C300.0419 (19)0.041 (2)0.0252 (16)−0.0100 (17)0.0003 (14)−0.0143 (15)
C310.0366 (18)0.039 (2)0.0256 (16)−0.0080 (16)−0.0022 (13)−0.0168 (15)
C320.045 (2)0.046 (2)0.0265 (17)−0.0101 (18)−0.0001 (14)−0.0161 (16)
C330.048 (2)0.045 (2)0.0270 (17)−0.0095 (18)−0.0016 (15)−0.0146 (16)
C340.079 (3)0.047 (2)0.0354 (19)−0.026 (2)−0.0023 (19)−0.0202 (18)
C350.080 (3)0.044 (2)0.0317 (19)−0.027 (2)0.0051 (19)−0.0153 (17)
C360.059 (2)0.042 (2)0.0254 (17)−0.0114 (19)0.0003 (16)−0.0141 (16)
C370.057 (2)0.066 (3)0.0352 (19)−0.023 (2)−0.0017 (17)−0.024 (2)
C380.058 (2)0.061 (3)0.0301 (18)−0.031 (2)0.0017 (17)−0.0122 (18)
C390.0338 (19)0.074 (3)0.0337 (19)−0.016 (2)0.0024 (15)−0.0331 (19)
C400.034 (3)0.040 (4)0.029 (3)−0.009 (3)−0.008 (2)−0.011 (3)
C410.026 (3)0.062 (6)0.045 (3)−0.017 (3)−0.001 (2)−0.014 (3)
C420.032 (2)0.132 (5)0.037 (2)−0.028 (3)0.0003 (17)−0.043 (3)
C39'0.0338 (19)0.074 (3)0.0337 (19)−0.016 (2)0.0024 (15)−0.0331 (19)
C42'0.032 (2)0.132 (5)0.037 (2)−0.028 (3)0.0003 (17)−0.043 (3)

Geometric parameters (Å, °)

Cd—N12.320 (3)C9—H90.9300
Cd—N62.335 (3)C10—C111.446 (5)
Cd—N52.343 (3)C11—C121.374 (6)
Cd—N22.351 (3)C13—C141.483 (5)
Cd—O32.496 (3)C14—C151.384 (6)
Cd—O5i2.541 (3)C14—C191.390 (6)
Cd—O6i2.671 (3)C15—C161.388 (5)
Cd—O42.742 (3)C15—H150.9300
O1—C171.353 (5)C16—C171.382 (6)
O1—H1O0.8400C16—H160.9300
O2—C361.355 (4)C17—C181.385 (6)
O2—H2O0.8401C18—C191.376 (6)
O3—C39'1.246 (5)C18—H180.9300
O3—C391.246 (5)C19—H190.9300
O4—C39'1.249 (5)C20—C211.385 (5)
O4—C391.249 (5)C20—H200.9300
O5—C42'1.267 (6)C21—C221.358 (5)
O5—C421.267 (6)C21—H210.9300
O5—Cdii2.541 (3)C22—C231.408 (5)
O6—C42'1.220 (6)C22—H220.9300
O6—C421.220 (6)C23—C241.416 (5)
N1—C11.323 (5)C23—C311.422 (5)
N1—C51.350 (5)C24—C251.452 (5)
N2—C71.317 (5)C25—C291.404 (5)
N2—C61.361 (4)C26—C271.385 (6)
N3—C131.315 (5)C26—H260.9300
N3—C121.393 (4)C27—C281.364 (5)
N3—H3n0.8600C27—H270.9300
N4—C131.339 (5)C28—C291.398 (5)
N4—C111.376 (5)C28—H280.9300
N5—C201.325 (5)C29—C301.439 (5)
N5—C241.351 (4)C30—C311.370 (5)
N6—C261.318 (5)C32—C331.479 (5)
N6—C251.363 (4)C33—C341.385 (6)
N7—C321.357 (5)C33—C381.396 (5)
N7—C311.379 (4)C34—C351.385 (5)
N7—H7n0.8600C34—H340.9300
N8—C321.312 (5)C35—C361.385 (5)
N8—C301.386 (4)C35—H350.9300
C1—C21.391 (5)C36—C371.383 (6)
C1—H10.9300C37—C381.393 (5)
C2—C31.365 (6)C37—H370.9300
C2—H20.9300C38—H380.9300
C3—C41.392 (6)C39—C401.513 (6)
C3—H30.9300C40—C411.292 (12)
C4—C51.418 (5)C40—H400.9300
C4—C121.421 (5)C41—C421.535 (7)
C5—C61.460 (5)C41—H410.9300
C6—C101.398 (5)C39'—C40'1.593 (15)
C7—C81.406 (7)C40'—C41'1.30 (3)
C7—H70.9300C40'—H40'0.9300
C8—C91.350 (6)C41'—C42'1.611 (12)
C8—H80.9300C41'—H41'0.9300
C9—C101.390 (6)
N1—Cd—N6155.24 (10)C15—C14—C19118.7 (4)
N1—Cd—N5124.62 (11)C15—C14—C13120.8 (4)
N6—Cd—N571.47 (10)C19—C14—C13120.4 (4)
N1—Cd—N271.63 (11)C14—C15—C16120.7 (4)
N6—Cd—N2100.10 (10)C14—C15—H15119.6
N5—Cd—N2156.65 (10)C16—C15—H15119.6
N1—Cd—O378.07 (10)C17—C16—C15119.9 (4)
N6—Cd—O387.88 (10)C17—C16—H16120.0
N5—Cd—O379.62 (9)C15—C16—H16120.0
N2—Cd—O3122.59 (9)O1—C17—C16122.6 (4)
N1—Cd—O5i78.38 (10)O1—C17—C18117.7 (4)
N6—Cd—O5i125.81 (10)C16—C17—C18119.7 (4)
N5—Cd—O5i77.89 (11)C19—C18—C17120.1 (4)
N2—Cd—O5i90.86 (12)C19—C18—H18119.9
O3—Cd—O5i129.15 (12)C17—C18—H18119.9
N1—Cd—O6i119.07 (10)C18—C19—C14120.9 (4)
N6—Cd—O6i80.39 (10)C18—C19—H19119.6
N5—Cd—O6i78.73 (10)C14—C19—H19119.6
N2—Cd—O6i78.37 (10)N5—C20—C21123.2 (3)
O3—Cd—O6i157.74 (9)N5—C20—H20118.4
O5i—Cd—O6i50.03 (11)C21—C20—H20118.4
N1—Cd—O479.34 (9)C22—C21—C20118.9 (3)
N6—Cd—O476.05 (9)C22—C21—H21120.5
N5—Cd—O4119.50 (9)C20—C21—H21120.5
N2—Cd—O477.52 (10)C21—C22—C23119.8 (3)
O3—Cd—O449.28 (9)C21—C22—H22120.1
O5i—Cd—O4157.20 (9)C23—C22—H22120.1
O6i—Cd—O4142.46 (10)C22—C23—C24117.8 (3)
C17—O1—H1O116.3C22—C23—C31125.7 (3)
C36—O2—H2O113.5C24—C23—C31116.5 (3)
C39'—O3—C390.0 (3)N5—C24—C23120.9 (3)
C39'—O3—Cd98.9 (2)N5—C24—C25118.4 (3)
C39—O3—Cd98.9 (2)C23—C24—C25120.6 (3)
C39'—O4—C390.0 (3)N6—C25—C29121.2 (3)
C39'—O4—Cd87.2 (2)N6—C25—C24117.9 (3)
C39—O4—Cd87.2 (2)C29—C25—C24120.9 (3)
C42'—O5—C420.0 (5)N6—C26—C27123.6 (3)
C42'—O5—Cdii93.9 (3)N6—C26—H26118.2
C42—O5—Cdii93.9 (3)C27—C26—H26118.2
C42'—O6—C420.0 (8)C28—C27—C26119.2 (4)
C1—N1—C5119.1 (3)C28—C27—H27120.4
C1—N1—Cd124.2 (2)C26—C27—H27120.4
C5—N1—Cd116.6 (2)C27—C28—C29119.0 (3)
C7—N2—C6118.8 (3)C27—C28—H28120.5
C7—N2—Cd126.0 (3)C29—C28—H28120.5
C6—N2—Cd115.0 (2)C28—C29—C25118.6 (3)
C13—N3—C12106.8 (3)C28—C29—C30124.0 (3)
C13—N3—H3n126.6C25—C29—C30117.4 (3)
C12—N3—H3n126.6C31—C30—N8111.1 (3)
C13—N4—C11103.9 (3)C31—C30—C29120.8 (3)
C20—N5—C24119.3 (3)N8—C30—C29128.1 (3)
C20—N5—Cd124.9 (2)C30—C31—N7105.1 (3)
C24—N5—Cd115.6 (2)C30—C31—C23123.6 (3)
C26—N6—C25118.4 (3)N7—C31—C23131.3 (3)
C26—N6—Cd125.7 (2)N8—C32—N7113.3 (3)
C25—N6—Cd115.6 (2)N8—C32—C33123.2 (3)
C32—N7—C31106.6 (3)N7—C32—C33123.4 (3)
C32—N7—H7n126.7C34—C33—C38118.5 (3)
C31—N7—H7n126.7C34—C33—C32120.0 (3)
C32—N8—C30103.9 (3)C38—C33—C32121.5 (3)
N1—C1—C2123.6 (4)C35—C34—C33121.1 (4)
N1—C1—H1118.2C35—C34—H34119.5
C2—C1—H1118.2C33—C34—H34119.5
C3—C2—C1118.1 (4)C34—C35—C36120.0 (4)
C3—C2—H2121.0C34—C35—H35120.0
C1—C2—H2121.0C36—C35—H35120.0
C2—C3—C4120.2 (3)O2—C36—C37122.7 (3)
C2—C3—H3119.9O2—C36—C35117.3 (3)
C4—C3—H3119.9C37—C36—C35120.0 (3)
C3—C4—C5118.2 (3)C36—C37—C38119.7 (4)
C3—C4—C12125.6 (3)C36—C37—H37120.2
C5—C4—C12116.2 (3)C38—C37—H37120.2
N1—C5—C4120.8 (3)C37—C38—C33120.7 (4)
N1—C5—C6118.0 (3)C37—C38—H38119.6
C4—C5—C6121.1 (3)C33—C38—H38119.6
N2—C6—C10121.3 (3)O3—C39—O4123.3 (3)
N2—C6—C5118.0 (3)O3—C39—C40109.8 (4)
C10—C6—C5120.7 (3)O4—C39—C40126.9 (4)
N2—C7—C8122.8 (4)C41—C40—C39120.1 (7)
N2—C7—H7118.6C41—C40—H40119.9
C8—C7—H7118.6C39—C40—H40119.9
C9—C8—C7118.5 (4)C40—C41—C42121.5 (7)
C9—C8—H8120.7C40—C41—H41119.2
C7—C8—H8120.7C42—C41—H41119.2
C8—C9—C10120.2 (4)O6—C42—O5125.1 (4)
C8—C9—H9119.9O6—C42—C41110.8 (5)
C10—C9—H9119.9O5—C42—C41123.5 (5)
C9—C10—C6118.4 (4)O3—C39'—O4123.3 (3)
C9—C10—C11124.4 (4)O3—C39'—C40'133.1 (7)
C6—C10—C11117.2 (4)O4—C39'—C40'101.1 (7)
C12—C11—N4110.3 (3)C41'—C40'—C39'114.1 (14)
C12—C11—C10121.3 (3)C41'—C40'—H40'123.0
N4—C11—C10128.4 (4)C39'—C40'—H40'123.0
C11—C12—N3105.4 (3)C40'—C41'—C42'108.8 (14)
C11—C12—C4123.4 (3)C40'—C41'—H41'125.6
N3—C12—C4131.1 (4)C42'—C41'—H41'125.6
N3—C13—N4113.6 (3)O6—C42'—O5125.1 (4)
N3—C13—C14125.3 (4)O6—C42'—C41'138.0 (6)
N4—C13—C14121.1 (4)O5—C42'—C41'95.3 (6)
N1—Cd—O3—C39'−92.7 (2)C13—N3—C12—C4177.4 (4)
N6—Cd—O3—C39'66.8 (2)C3—C4—C12—C11−178.4 (4)
N5—Cd—O3—C39'138.3 (2)C5—C4—C12—C111.0 (5)
N2—Cd—O3—C39'−33.9 (3)C3—C4—C12—N34.9 (6)
O5i—Cd—O3—C39'−156.8 (2)C5—C4—C12—N3−175.7 (4)
O6i—Cd—O3—C39'124.7 (3)C12—N3—C13—N40.3 (5)
O4—Cd—O3—C39'−6.6 (2)C12—N3—C13—C14−177.5 (4)
N1—Cd—O3—C39−92.7 (2)C11—N4—C13—N3−0.7 (5)
N6—Cd—O3—C3966.8 (2)C11—N4—C13—C14177.2 (4)
N5—Cd—O3—C39138.3 (2)N3—C13—C14—C1527.2 (6)
N2—Cd—O3—C39−33.9 (3)N4—C13—C14—C15−150.5 (4)
O5i—Cd—O3—C39−156.8 (2)N3—C13—C14—C19−158.0 (4)
O6i—Cd—O3—C39124.7 (3)N4—C13—C14—C1924.4 (6)
O4—Cd—O3—C39−6.6 (2)C19—C14—C15—C16−0.1 (6)
N1—Cd—O4—C39'89.9 (2)C13—C14—C15—C16174.9 (4)
N6—Cd—O4—C39'−92.9 (2)C14—C15—C16—C17−0.6 (6)
N5—Cd—O4—C39'−34.0 (2)C15—C16—C17—O1−178.4 (4)
N2—Cd—O4—C39'163.2 (2)C15—C16—C17—C181.7 (6)
O3—Cd—O4—C39'6.5 (2)O1—C17—C18—C19178.1 (4)
O5i—Cd—O4—C39'102.3 (4)C16—C17—C18—C19−2.1 (7)
O6i—Cd—O4—C39'−145.6 (2)C17—C18—C19—C141.4 (7)
N1—Cd—O4—C3989.9 (2)C15—C14—C19—C18−0.3 (7)
N6—Cd—O4—C39−92.9 (2)C13—C14—C19—C18−175.3 (4)
N5—Cd—O4—C39−34.0 (2)C24—N5—C20—C21−0.3 (5)
N2—Cd—O4—C39163.2 (2)Cd—N5—C20—C21174.6 (3)
O3—Cd—O4—C396.5 (2)N5—C20—C21—C22−0.6 (6)
O5i—Cd—O4—C39102.3 (4)C20—C21—C22—C230.3 (6)
O6i—Cd—O4—C39−145.6 (2)C21—C22—C23—C240.7 (5)
N6—Cd—N1—C1−108.9 (3)C21—C22—C23—C31−178.9 (4)
N5—Cd—N1—C116.1 (3)C20—N5—C24—C231.3 (5)
N2—Cd—N1—C1177.3 (3)Cd—N5—C24—C23−174.0 (2)
O3—Cd—N1—C1−52.2 (3)C20—N5—C24—C25−177.9 (3)
O5i—Cd—N1—C182.4 (3)Cd—N5—C24—C256.8 (4)
O6i—Cd—N1—C1112.6 (3)C22—C23—C24—N5−1.5 (5)
O4—Cd—N1—C1−102.5 (3)C31—C23—C24—N5178.1 (3)
N6—Cd—N1—C567.0 (4)C22—C23—C24—C25177.7 (3)
N5—Cd—N1—C5−168.0 (2)C31—C23—C24—C25−2.7 (5)
N2—Cd—N1—C5−6.8 (2)C26—N6—C25—C29−1.6 (5)
O3—Cd—N1—C5123.7 (2)Cd—N6—C25—C29173.1 (3)
O5i—Cd—N1—C5−101.7 (2)C26—N6—C25—C24176.9 (3)
O6i—Cd—N1—C5−71.5 (3)Cd—N6—C25—C24−8.4 (4)
O4—Cd—N1—C573.4 (2)N5—C24—C25—N61.0 (4)
N1—Cd—N2—C7−178.2 (3)C23—C24—C25—N6−178.2 (3)
N6—Cd—N2—C726.0 (3)N5—C24—C25—C29179.6 (3)
N5—Cd—N2—C7−40.3 (5)C23—C24—C25—C290.4 (5)
O3—Cd—N2—C7119.9 (3)C25—N6—C26—C270.3 (6)
O5i—Cd—N2—C7−100.7 (3)Cd—N6—C26—C27−173.8 (3)
O6i—Cd—N2—C7−51.9 (3)N6—C26—C27—C281.3 (7)
O4—Cd—N2—C799.1 (3)C26—C27—C28—C29−1.6 (7)
N1—Cd—N2—C67.5 (2)C27—C28—C29—C250.4 (6)
N6—Cd—N2—C6−148.4 (2)C27—C28—C29—C30−179.6 (4)
N5—Cd—N2—C6145.3 (3)N6—C25—C29—C281.3 (5)
O3—Cd—N2—C6−54.4 (3)C24—C25—C29—C28−177.3 (3)
O5i—Cd—N2—C684.9 (3)N6—C25—C29—C30−178.7 (3)
O6i—Cd—N2—C6133.7 (3)C24—C25—C29—C302.7 (5)
O4—Cd—N2—C6−75.3 (2)C32—N8—C30—C310.2 (4)
N1—Cd—N5—C2018.2 (3)C32—N8—C30—C29−179.7 (4)
N6—Cd—N5—C20177.0 (3)C28—C29—C30—C31176.4 (4)
N2—Cd—N5—C20−111.1 (3)C25—C29—C30—C31−3.6 (5)
O3—Cd—N5—C2085.7 (3)C28—C29—C30—N8−3.7 (6)
O5i—Cd—N5—C20−48.3 (3)C25—C29—C30—N8176.3 (4)
O6i—Cd—N5—C20−99.5 (3)N8—C30—C31—N70.1 (4)
O4—Cd—N5—C20115.8 (3)C29—C30—C31—N7180.0 (3)
N1—Cd—N5—C24−166.8 (2)N8—C30—C31—C23−178.6 (3)
N6—Cd—N5—C24−8.0 (2)C29—C30—C31—C231.3 (6)
N2—Cd—N5—C2464.0 (4)C32—N7—C31—C30−0.3 (4)
O3—Cd—N5—C24−99.2 (2)C32—N7—C31—C23178.2 (4)
O5i—Cd—N5—C24126.7 (2)C22—C23—C31—C30−178.5 (3)
O6i—Cd—N5—C2475.5 (2)C24—C23—C31—C301.9 (5)
O4—Cd—N5—C24−69.2 (2)C22—C23—C31—N73.2 (6)
N1—Cd—N6—C26−42.5 (5)C24—C23—C31—N7−176.4 (3)
N5—Cd—N6—C26−177.2 (3)C30—N8—C32—N7−0.4 (4)
N2—Cd—N6—C2625.3 (3)C30—N8—C32—C33176.7 (3)
O3—Cd—N6—C26−97.5 (3)C31—N7—C32—N80.5 (4)
O5i—Cd—N6—C26123.7 (3)C31—N7—C32—C33−176.6 (3)
O6i—Cd—N6—C26101.5 (3)N8—C32—C33—C3425.9 (6)
O4—Cd—N6—C26−49.0 (3)N7—C32—C33—C34−157.3 (4)
N1—Cd—N6—C25143.2 (3)N8—C32—C33—C38−150.9 (4)
N5—Cd—N6—C258.5 (2)N7—C32—C33—C3825.9 (6)
N2—Cd—N6—C25−149.0 (2)C38—C33—C34—C351.3 (7)
O3—Cd—N6—C2588.3 (2)C32—C33—C34—C35−175.6 (4)
O5i—Cd—N6—C25−50.5 (3)C33—C34—C35—C360.7 (7)
O6i—Cd—N6—C25−72.7 (2)C34—C35—C36—O2179.6 (4)
O4—Cd—N6—C25136.7 (3)C34—C35—C36—C37−2.2 (7)
C5—N1—C1—C21.1 (5)O2—C36—C37—C38179.9 (4)
Cd—N1—C1—C2176.9 (3)C35—C36—C37—C381.8 (7)
N1—C1—C2—C3−1.7 (6)C36—C37—C38—C330.2 (7)
C1—C2—C3—C40.8 (6)C34—C33—C38—C37−1.7 (7)
C2—C3—C4—C50.5 (5)C32—C33—C38—C37175.1 (4)
C2—C3—C4—C12180.0 (4)C39'—O3—C39—O40(46)
C1—N1—C5—C40.3 (5)Cd—O3—C39—O413.2 (4)
Cd—N1—C5—C4−175.8 (2)C39'—O3—C39—C400(100)
C1—N1—C5—C6−178.3 (3)Cd—O3—C39—C40−170.0 (3)
Cd—N1—C5—C65.6 (4)C39'—O4—C39—O30(35)
C3—C4—C5—N1−1.1 (5)Cd—O4—C39—O3−11.9 (4)
C12—C4—C5—N1179.4 (3)C39'—O4—C39—C400(100)
C3—C4—C5—C6177.4 (3)Cd—O4—C39—C40171.8 (4)
C12—C4—C5—C6−2.1 (5)O3—C39—C40—C41130.4 (6)
C7—N2—C6—C10−0.3 (5)O4—C39—C40—C41−52.9 (7)
Cd—N2—C6—C10174.5 (3)C39—C40—C41—C42−174.6 (4)
C7—N2—C6—C5177.7 (3)C42'—O6—C42—O50(100)
Cd—N2—C6—C5−7.5 (4)C42'—O6—C42—C410(27)
N1—C5—C6—N21.4 (5)C42'—O5—C42—O60(100)
C4—C5—C6—N2−177.2 (3)Cdii—O5—C42—O616.1 (5)
N1—C5—C6—C10179.4 (3)C42'—O5—C42—C410(19)
C4—C5—C6—C100.8 (5)Cdii—O5—C42—C41−154.0 (5)
C6—N2—C7—C81.5 (6)C40—C41—C42—O6176.2 (6)
Cd—N2—C7—C8−172.6 (3)C40—C41—C42—O5−12.4 (9)
N2—C7—C8—C9−1.3 (7)C39—O3—C39'—O40(46)
C7—C8—C9—C10−0.2 (7)Cd—O3—C39'—O413.2 (4)
C8—C9—C10—C61.4 (7)C39—O3—C39'—C40'0(100)
C8—C9—C10—C11−179.3 (4)Cd—O3—C39'—C40'−145.2 (8)
N2—C6—C10—C9−1.1 (6)C39—O4—C39'—O30(35)
C5—C6—C10—C9−179.0 (4)Cd—O4—C39'—O3−11.9 (4)
N2—C6—C10—C11179.5 (3)C39—O4—C39'—C40'0(100)
C5—C6—C10—C111.6 (5)Cd—O4—C39'—C40'152.2 (5)
C13—N4—C11—C120.9 (5)O3—C39'—C40'—C41'−21.0 (16)
C13—N4—C11—C10−178.6 (4)O4—C39'—C40'—C41'177.3 (10)
C9—C10—C11—C12178.0 (4)C39'—C40'—C41'—C42'−175.4 (7)
C6—C10—C11—C12−2.6 (6)C42—O6—C42'—O50(100)
C9—C10—C11—N4−2.6 (7)C42—O6—C42'—C41'0(20)
C6—C10—C11—N4176.8 (4)C42—O5—C42'—O60(100)
N4—C11—C12—N3−0.7 (4)Cdii—O5—C42'—O616.1 (5)
C10—C11—C12—N3178.8 (3)C42—O5—C42'—C41'0(24)
N4—C11—C12—C4−178.1 (3)Cdii—O5—C42'—C41'−176.4 (5)
C10—C11—C12—C41.4 (6)C40'—C41'—C42'—O6−61.2 (13)
C13—N3—C12—C110.3 (4)C40'—C41'—C42'—O5134.2 (10)

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

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1O···O6iii0.841.862.659 (5)161
O2—H2O···O4iv0.841.832.663 (5)172
N3—H3n···O5v0.862.152.893 (6)144
N7—H7n···O3vi0.862.062.785 (6)141
C3—H3···O5v0.932.483.309 (5)148
C22—H22···O3vi0.932.573.360 (5)143
C28—H28···O2vii0.932.553.390 (6)150
C2—H2···Cg1vi0.932.753.445 (5)133
C21—H21···Cg2viii0.932.793.554 (5)140

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2849).

References

  • Brandenburg, K. (2006). DIAMOND Crystal Impact GbR, Bonn, Germany.
  • Bruker (1997). SMART Bruker AXS Inc., Madison, Wisconsin, USA.
  • Bruker (1999). SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Chen, X.-M. & Liu, G.-F. (2002). Chem. Eur. J.8, 4811–4817. [PubMed]
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Yang, J., Li, G.-D., Cao, J.-J., Yue, Q., Li, G.-H. & Chen, J.-S. (2007a). Chem. Eur. J.13, 3248–3261. [PubMed]
  • Yang, J., Ma, J.-F., Liu, Y.-Y., Ma, J.-C. & Batten, S. R. (2007b). Inorg. Chem.46, 6542–6555. [PubMed]

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