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Acta Crystallogr Sect E Struct Rep Online. 2008 November 1; 64(Pt 11): m1427–m1428.
Published online 2008 October 18. doi:  10.1107/S1600536808033138
PMCID: PMC2959761

(Benzene-1,3-dicarboxyl­ato-κ2 O 1,O 1′)(1,12,15,26-tetra­aza-5,8,19,22-tetra­oxa-3,4:9,10:17,18:23,24-tetra­benzocyclo­octa­cosane-κ4 N 1,N 12,N 15,N 26)cadmium(II) benzene-1,3-dicarboxylic acid solvate

Abstract

In the title compound, [Cd(C8H4O4)(C36H44N4O4)]·C8H6O4, the CdII atom is six-coordinated by four N atoms from the macrocyclic ligand and two O atoms from a benzene-1,3-dicarboxyl­ate ligand. The complex mol­ecules are linked by N—H(...)O hydrogen bonds, forming a one-dimensional chain structure along the b axis. The chains are further connected through N—H(...)O and O—H(...)O hydrogen bonds between the complex mol­ecule and an uncoordinated benzene-1,3-dicarboxylic acid mol­ecule, resulting in a two-dimensional supra­molecular network.

Related literature

For general background, see: Banerjee et al. (2005 [triangle]); Liu et al. (2005 [triangle]). For a related structure, see: Sarkar et al. (2008 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-m1427-scheme1.jpg

Experimental

Crystal data

  • [Cd(C8H4O4)(C36H44N4O4)]·C8H6O4
  • M r = 1039.39
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-m1427-efi1.jpg
  • a = 12.912 (3) Å
  • b = 23.330 (5) Å
  • c = 16.086 (3) Å
  • β = 103.37 (3)°
  • V = 4714.4 (18) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.53 mm−1
  • T = 293 (2) K
  • 0.34 × 0.29 × 0.21 mm

Data collection

  • Rigaku R-AXIS RAPID diffractometer
  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995 [triangle]) T min = 0.842, T max = 0.913
  • 43452 measured reflections
  • 10582 independent reflections
  • 4951 reflections with I > 2σ(I)
  • R int = 0.158

Refinement

  • R[F 2 > 2σ(F 2)] = 0.085
  • wR(F 2) = 0.185
  • S = 1.02
  • 10582 reflections
  • 640 parameters
  • 9 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.68 e Å−3
  • Δρmin = −0.71 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 1998 [triangle]); cell refinement: PROCESS-AUTO; data reduction: PROCESS-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]) and DIAMOND (Brandenburg, 1999 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Selected geometric parameters (Å, °)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808033138/hy2157sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808033138/hy2157Isup2.hkl

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

Acknowledgments

The authors thank the National Natural Science Foundation of China (grant No. 20471014), the Program for New Century Excellent Talents in Chinese Universities (grant No. NCET-05-0320) and the Analysis and Testing Foundation of Northeast Normal University for support.

supplementary crystallographic information

Comment

As part of an investigation of the supramolecular chemistry of crown ether systems, we present here the crystal structure of the title compound.

In the title compound, the CdII atom displays a psudo-square-pyramidal coordination geometry, defined by four N atoms from the macrocyclic ligand in the basal plane and two O atoms of the carboxylate group of a benzene-1,3-dicarboxylate ligand (Fig. 1). The bond distances (Cd—N, Cd—O) and angles (N—Cd—N, N—Cd—O) are normal (Table 1) (Banerjee et al., 2005; Liu et al., 2005). The complex molecules are linked by N—H···O hydrogen bonds, forming a one-dimensional chain structure along the b-axis (Table 2). The uncoordinated benzene-1,3-dicarboxylic acid molecules are located on both sides of the chain. The adjacent chains are further connected through N—H···O and O—H···O hydrogen bonds between the complex molecule and the benzene-1,3-dicarboxylic acid, resulting in a two-dimensional supramolecular network (Fig. 2) (Sarkar et al., 2008).

Experimental

A mixture of Cd(OH)2 (0.146 g, 1 mmol), benzene-1,3-dicarboxylic acid (0.162 g, 1 mmol) and 3,4:9,10:17,18:23,24-tetrabenzo-1,12,15,26-tetraaza-5,8,19,22- tetraoxacyclooctacosane (0.596 g, 1 mmol) in EtOH (10 ml) was placed in a 20 ml Teflon-lined reactor and heated at 393 K for 3 d. After the reactor was gradually cooled to room temperature at a rate of 10 K h-1, colorless crystals were obtained.

Refinement

H atoms bound to C atoms were positioned geometrically and refined as riding, with C—H = 0.93 (CH) and 0.97 Å (CH2) and with Uiso(H) = 1.2Ueq(C). H atoms bound to N and O atoms were located in a difference Fourier map and refined with restraints of N—H = 0.84 (2) and O—H = 0.86 (2) Å and with Uiso(H) = 1.2Ueq(N) or Uiso(H) = 1.5Ueq(O).

Figures

Fig. 1.
Molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. H atoms have been omitted for clarity.
Fig. 2.
View of the two-dimensional supramolecular structure of the title compound. Hydrogen bonds are shown as dashed lines.

Crystal data

[Cd(C8H4O4)(C36H44N4O4)]·C8H6O4F(000) = 2152
Mr = 1039.39Dx = 1.464 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 10582 reflections
a = 12.912 (3) Åθ = 3.1–27.5°
b = 23.330 (5) ŵ = 0.53 mm1
c = 16.086 (3) ÅT = 293 K
β = 103.37 (3)°Block, colourless
V = 4714.4 (18) Å30.34 × 0.29 × 0.21 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID diffractometer10582 independent reflections
Radiation source: 18 kW rotation anode4951 reflections with I > 2σ(I)
graphiteRint = 0.158
ω scansθmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)h = −16→15
Tmin = 0.842, Tmax = 0.913k = −30→30
43452 measured reflectionsl = −20→20

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)] = 0.085Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.185H atoms treated by a mixture of independent and constrained refinement
S = 1.02w = 1/[σ2(Fo2) + (0.0557P)2 + 6.3548P] where P = (Fo2 + 2Fc2)/3
10582 reflections(Δ/σ)max = 0.001
640 parametersΔρmax = 0.68 e Å3
9 restraintsΔρmin = −0.71 e Å3

Special details

Refinement. The crystal quality is not fine and weakly diffracting, so that the value of R(int) is greater than 0.15.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
Cd10.82429 (4)0.70844 (2)0.68005 (3)0.04757 (17)
C10.7605 (6)0.6571 (3)0.9444 (4)0.060 (2)
C20.6668 (8)0.6673 (4)0.9702 (6)0.090 (3)
H20.62280.69750.94630.108*
C30.6387 (9)0.6330 (7)1.0308 (7)0.126 (5)
H30.57690.64061.04920.151*
C40.7012 (12)0.5884 (6)1.0634 (6)0.122 (5)
H40.67940.56391.10160.147*
C50.7954 (11)0.5784 (5)1.0419 (6)0.109 (4)
H50.84020.54901.06750.131*
C60.8223 (8)0.6133 (4)0.9807 (5)0.074 (2)
C71.0047 (8)0.5921 (5)1.0100 (6)0.116 (4)
H7A0.99590.55611.03780.140*
H7B1.01770.62171.05350.140*
C81.1002 (8)0.5876 (5)0.9714 (7)0.116 (4)
H8A1.16460.58531.01650.140*
H8B1.09510.55320.93700.140*
C91.1934 (7)0.6434 (4)0.8896 (6)0.088 (3)
C101.2900 (8)0.6155 (5)0.9199 (6)0.115 (4)
H101.29770.58870.96360.138*
C111.3740 (9)0.6284 (6)0.8837 (9)0.125 (5)
H111.43890.60990.90300.150*
C121.3626 (8)0.6679 (5)0.8201 (9)0.118 (4)
H121.41980.67700.79640.142*
C131.2657 (7)0.6944 (4)0.7910 (6)0.090 (3)
H131.25870.72130.74740.108*
C141.1804 (6)0.6827 (3)0.8234 (5)0.068 (2)
C151.0722 (5)0.7088 (3)0.7890 (4)0.0609 (18)
H15A1.04600.72420.83630.073*
H15B1.07930.74050.75160.073*
C161.0233 (7)0.6366 (4)0.6768 (5)0.112 (4)
H16A0.99340.59840.67630.134*
H16B1.10020.63260.69170.134*
C170.9913 (7)0.6604 (5)0.5876 (5)0.109 (4)
H17A1.03140.69520.58450.131*
H17B1.00970.63290.54800.131*
C180.8618 (6)0.7140 (3)0.4908 (4)0.0618 (19)
H18A0.91040.74590.50700.074*
H18B0.78990.72890.48090.074*
C190.8784 (6)0.6886 (3)0.4090 (4)0.060 (2)
C200.9703 (7)0.6970 (4)0.3810 (5)0.078 (2)
H201.02520.71750.41610.094*
C210.9863 (8)0.6769 (4)0.3043 (6)0.088 (3)
H211.05010.68300.28820.106*
C220.9040 (9)0.6474 (4)0.2527 (5)0.089 (3)
H220.91150.63370.20010.107*
C230.8087 (8)0.6377 (4)0.2782 (5)0.079 (3)
H230.75310.61800.24260.095*
C240.7984 (6)0.6576 (3)0.3560 (4)0.061 (2)
C250.6174 (6)0.6254 (3)0.3339 (5)0.069 (2)
H25A0.63260.58850.31150.083*
H25B0.59300.65130.28620.083*
C260.5341 (6)0.6190 (3)0.3835 (5)0.071 (2)
H26A0.46840.60560.34630.085*
H26B0.55670.59100.42860.085*
C270.4366 (6)0.6752 (3)0.4613 (5)0.062 (2)
C280.3364 (6)0.6499 (3)0.4314 (5)0.071 (2)
H280.32220.62790.38190.086*
C290.2600 (6)0.6585 (4)0.4766 (7)0.088 (3)
H290.19430.64060.45830.105*
C300.2770 (7)0.6917 (4)0.5464 (7)0.095 (3)
H300.22290.69790.57470.115*
C310.3760 (7)0.7167 (4)0.5760 (5)0.080 (3)
H310.38760.73990.62420.096*
C320.4574 (6)0.7078 (3)0.5354 (4)0.0611 (19)
C330.5690 (5)0.7290 (3)0.5729 (4)0.061 (2)
H33A0.59430.74990.52930.073*
H33B0.56740.75540.61910.073*
C340.6087 (6)0.6435 (3)0.6662 (4)0.064 (2)
H34A0.64000.60590.66450.077*
H34B0.53190.63940.64920.077*
C350.6395 (5)0.6666 (3)0.7562 (4)0.0595 (19)
H35A0.61050.70490.75740.071*
H35B0.60900.64250.79340.071*
C360.7893 (6)0.6938 (3)0.8745 (4)0.060 (2)
H36A0.75620.73110.87440.072*
H36B0.86580.69950.88780.072*
C380.7114 (7)0.5151 (4)0.5534 (5)0.071 (2)
C390.7151 (6)0.4983 (3)0.4656 (5)0.0593 (19)
C400.6242 (6)0.4738 (3)0.4124 (5)0.072 (2)
H400.56290.46770.43220.086*
C410.6280 (8)0.4590 (4)0.3298 (5)0.086 (3)
H410.56880.44220.29410.104*
C420.7189 (8)0.4687 (3)0.2990 (6)0.081 (2)
H420.71950.45900.24300.097*
C430.8081 (6)0.4928 (3)0.3516 (5)0.067 (2)
C440.8058 (6)0.5070 (3)0.4330 (5)0.065 (2)
H440.86620.52300.46830.078*
C450.9072 (7)0.5032 (4)0.3212 (7)0.078 (2)
C460.6529 (6)1.0083 (3)0.7105 (5)0.066 (2)
C470.7441 (6)0.9768 (3)0.6899 (4)0.0484 (16)
C480.7501 (6)0.9177 (3)0.6919 (4)0.0528 (17)
H480.69590.89670.70690.063*
C490.8341 (6)0.8891 (3)0.6723 (4)0.058 (2)
C500.9124 (6)0.9191 (3)0.6491 (4)0.063 (2)
H500.96920.89960.63570.075*
C510.9097 (7)0.9778 (3)0.6448 (5)0.073 (2)
H510.96340.99810.62810.088*
C520.8253 (6)1.0064 (3)0.6661 (4)0.067 (2)
H520.82331.04620.66420.080*
C530.8379 (8)0.8241 (3)0.6773 (5)0.065 (2)
O10.5169 (4)0.6717 (2)0.4188 (3)0.0736 (15)
O20.7106 (4)0.6477 (2)0.3893 (3)0.0721 (15)
O30.9132 (6)0.6043 (3)0.9519 (4)0.114 (2)
O41.1044 (6)0.6339 (3)0.9226 (4)0.117 (2)
O60.9880 (5)0.5205 (3)0.3692 (5)0.108 (2)
O70.6451 (5)0.4982 (3)0.5886 (4)0.105 (2)
O90.6665 (4)1.0564 (2)0.7453 (3)0.0647 (13)
O100.5626 (5)0.9828 (3)0.6893 (4)0.100 (2)
O110.7628 (5)0.7989 (2)0.6994 (4)0.0899 (19)
O120.9136 (5)0.7986 (2)0.6586 (4)0.0844 (17)
N10.6446 (5)0.6817 (3)0.6058 (4)0.0567 (16)
H1N0.654 (6)0.660 (3)0.566 (3)0.068*
N20.7561 (4)0.6687 (2)0.7885 (3)0.0499 (14)
H2N0.776 (5)0.6348 (12)0.789 (4)0.060*
N30.8784 (5)0.6731 (3)0.5614 (4)0.0558 (15)
H3N0.843 (5)0.6439 (19)0.547 (4)0.067*
N40.9934 (5)0.6679 (3)0.7413 (4)0.0573 (16)
H4N0.981 (6)0.649 (3)0.783 (3)0.069*
O50.8952 (6)0.4924 (3)0.2400 (5)0.108 (2)
H5O0.953 (5)0.503 (5)0.228 (7)0.162*
O80.7893 (5)0.5506 (3)0.5885 (3)0.0796 (16)
H8O0.795 (7)0.549 (4)0.6431 (17)0.119*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cd10.0465 (3)0.0453 (3)0.0494 (3)0.0013 (3)0.0079 (2)0.0025 (3)
C10.066 (5)0.064 (5)0.046 (4)−0.005 (4)0.005 (4)−0.009 (4)
C20.081 (7)0.116 (8)0.074 (6)0.007 (6)0.017 (5)0.011 (6)
C30.091 (8)0.215 (15)0.070 (7)−0.046 (9)0.015 (6)0.017 (8)
C40.150 (12)0.157 (13)0.057 (6)−0.067 (10)0.017 (8)0.009 (7)
C50.169 (12)0.087 (8)0.061 (6)0.002 (8)0.002 (7)0.015 (5)
C60.103 (7)0.067 (6)0.045 (4)0.013 (5)0.004 (5)0.004 (4)
C70.119 (9)0.145 (10)0.079 (6)0.001 (8)0.009 (7)0.043 (7)
C80.128 (10)0.103 (9)0.108 (8)0.035 (7)0.008 (7)0.030 (7)
C90.063 (6)0.114 (8)0.075 (6)0.021 (5)−0.007 (5)−0.012 (6)
C100.087 (7)0.150 (10)0.082 (6)0.051 (7)−0.033 (6)−0.036 (6)
C110.057 (6)0.150 (12)0.145 (11)0.031 (8)−0.020 (7)−0.052 (9)
C120.060 (7)0.126 (10)0.164 (12)−0.006 (7)0.015 (8)−0.066 (9)
C130.057 (5)0.084 (7)0.122 (8)−0.018 (5)0.007 (5)−0.029 (5)
C140.050 (4)0.072 (5)0.072 (5)0.000 (4)−0.006 (4)−0.017 (5)
C150.057 (4)0.056 (4)0.065 (4)0.000 (4)0.005 (4)−0.009 (4)
C160.082 (7)0.139 (9)0.098 (7)0.050 (6)−0.015 (6)−0.042 (7)
C170.079 (6)0.175 (11)0.076 (6)0.056 (7)0.024 (5)0.019 (6)
C180.074 (5)0.049 (4)0.059 (4)−0.010 (4)0.009 (4)−0.001 (4)
C190.066 (5)0.062 (5)0.053 (4)−0.004 (4)0.016 (4)0.007 (3)
C200.085 (6)0.086 (7)0.065 (5)−0.010 (5)0.019 (5)0.004 (4)
C210.090 (7)0.096 (7)0.084 (6)−0.007 (6)0.032 (6)0.012 (5)
C220.125 (8)0.094 (7)0.059 (5)−0.002 (6)0.041 (6)−0.002 (5)
C230.103 (7)0.085 (6)0.048 (4)−0.014 (5)0.015 (5)−0.013 (4)
C240.068 (5)0.062 (5)0.054 (4)−0.001 (4)0.013 (4)0.005 (4)
C250.070 (5)0.062 (5)0.065 (5)−0.007 (4)−0.005 (4)−0.013 (4)
C260.072 (5)0.062 (5)0.078 (5)−0.006 (4)0.015 (5)−0.009 (4)
C270.055 (5)0.064 (5)0.063 (5)0.001 (4)0.007 (4)0.013 (4)
C280.064 (5)0.067 (6)0.076 (5)−0.002 (4)0.001 (5)0.007 (4)
C290.044 (5)0.091 (7)0.119 (8)0.011 (5)0.000 (5)0.023 (6)
C300.060 (6)0.117 (9)0.111 (8)0.011 (5)0.022 (6)−0.001 (6)
C310.066 (5)0.105 (7)0.067 (5)0.024 (5)0.010 (4)0.004 (5)
C320.062 (5)0.066 (5)0.051 (4)0.013 (4)0.003 (4)0.009 (4)
C330.059 (4)0.057 (5)0.060 (4)0.004 (4)0.004 (4)0.001 (3)
C340.059 (5)0.051 (5)0.074 (5)−0.009 (4)0.002 (4)0.008 (4)
C350.055 (4)0.061 (5)0.064 (5)0.007 (4)0.017 (4)0.008 (4)
C360.063 (5)0.058 (5)0.057 (4)−0.003 (4)0.006 (4)−0.005 (3)
C380.077 (6)0.071 (6)0.070 (5)−0.010 (5)0.023 (5)0.003 (4)
C390.060 (5)0.053 (5)0.071 (5)−0.001 (4)0.026 (4)0.010 (4)
C400.068 (5)0.070 (6)0.085 (6)−0.017 (4)0.031 (5)−0.008 (4)
C410.093 (7)0.087 (7)0.076 (6)−0.025 (5)0.015 (5)−0.015 (5)
C420.102 (7)0.065 (6)0.082 (6)−0.009 (5)0.039 (6)−0.007 (4)
C430.078 (6)0.063 (5)0.069 (5)−0.001 (4)0.032 (5)−0.002 (4)
C440.063 (5)0.052 (5)0.087 (6)0.003 (4)0.032 (4)0.006 (4)
C450.085 (7)0.071 (6)0.094 (7)0.010 (5)0.054 (6)0.010 (5)
C460.068 (5)0.056 (5)0.081 (5)−0.006 (4)0.032 (4)0.003 (4)
C470.060 (4)0.046 (4)0.044 (4)0.000 (3)0.021 (3)−0.008 (3)
C480.063 (5)0.050 (5)0.049 (4)−0.009 (4)0.020 (4)−0.003 (3)
C490.073 (5)0.045 (4)0.047 (4)−0.002 (4)−0.005 (4)−0.002 (3)
C500.063 (5)0.061 (5)0.065 (5)0.013 (4)0.018 (4)−0.010 (4)
C510.085 (6)0.057 (6)0.084 (6)−0.003 (5)0.034 (5)0.008 (4)
C520.078 (5)0.049 (4)0.076 (5)0.002 (4)0.024 (5)0.005 (4)
C530.080 (6)0.050 (5)0.055 (4)0.009 (5)−0.008 (4)−0.006 (4)
O10.074 (4)0.073 (4)0.079 (4)−0.007 (3)0.027 (3)−0.011 (3)
O20.066 (3)0.091 (4)0.058 (3)−0.013 (3)0.011 (3)−0.011 (3)
O30.112 (5)0.157 (7)0.067 (4)0.064 (5)0.007 (4)0.019 (4)
O40.104 (5)0.155 (7)0.093 (5)0.046 (5)0.027 (4)0.050 (5)
O60.072 (4)0.138 (6)0.123 (5)−0.005 (4)0.038 (4)0.008 (5)
O70.107 (5)0.130 (6)0.093 (4)−0.040 (4)0.054 (4)−0.021 (4)
O90.084 (4)0.043 (3)0.074 (3)−0.004 (3)0.033 (3)−0.012 (2)
O100.083 (4)0.093 (5)0.138 (5)−0.019 (4)0.052 (4)−0.039 (4)
O110.110 (5)0.050 (4)0.104 (4)0.001 (3)0.013 (4)−0.003 (3)
O120.090 (4)0.054 (4)0.104 (4)0.018 (3)0.013 (3)−0.008 (3)
N10.050 (3)0.063 (4)0.051 (4)0.005 (3)−0.002 (3)−0.010 (3)
N20.047 (3)0.047 (3)0.053 (3)−0.001 (3)0.006 (3)−0.004 (3)
N30.049 (4)0.068 (4)0.050 (3)0.006 (3)0.010 (3)0.008 (3)
N40.050 (3)0.057 (4)0.058 (4)0.006 (3)−0.001 (3)0.000 (3)
O50.130 (6)0.102 (5)0.116 (5)−0.012 (5)0.075 (5)−0.006 (4)
O80.090 (4)0.077 (4)0.068 (3)−0.022 (3)0.012 (3)0.003 (3)

Geometric parameters (Å, °)

Cd1—N12.433 (6)C26—O11.392 (8)
Cd1—N22.321 (6)C26—H26A0.9700
Cd1—N32.329 (6)C26—H26B0.9700
Cd1—N42.374 (6)C27—O11.370 (9)
Cd1—O112.302 (6)C27—C321.387 (10)
Cd1—O122.462 (6)C27—C281.401 (10)
Cd1—C532.706 (8)C28—C291.369 (11)
C1—C61.344 (10)C28—H280.9300
C1—C21.388 (11)C29—C301.341 (12)
C1—C361.526 (10)C29—H290.9300
C2—C31.373 (13)C30—C311.384 (12)
C2—H20.9300C30—H300.9300
C3—C41.346 (16)C31—C321.376 (10)
C3—H30.9300C31—H310.9300
C4—C51.360 (15)C32—C331.510 (9)
C4—H40.9300C33—N11.487 (8)
C5—C61.383 (13)C33—H33A0.9700
C5—H50.9300C33—H33B0.9700
C6—O31.375 (10)C34—N11.471 (9)
C7—O31.357 (10)C34—C351.509 (9)
C7—C81.507 (8)C34—H34A0.9700
C7—H7A0.9700C34—H34B0.9700
C7—H7B0.9700C35—N21.475 (8)
C8—O41.343 (11)C35—H35A0.9700
C8—H8A0.9700C35—H35B0.9700
C8—H8B0.9700C36—N21.471 (8)
C9—C141.385 (12)C36—H36A0.9700
C9—O41.391 (11)C36—H36B0.9700
C9—C101.392 (12)C38—O71.197 (9)
C10—C111.376 (15)C38—O81.325 (9)
C10—H100.9300C38—C391.478 (10)
C11—C121.361 (16)C39—C441.403 (10)
C11—H110.9300C39—C401.404 (10)
C12—C131.376 (13)C40—C411.386 (10)
C12—H120.9300C40—H400.9300
C13—C141.351 (11)C41—C421.394 (11)
C13—H130.9300C41—H410.9300
C14—C151.507 (10)C42—C431.380 (10)
C15—N41.475 (9)C42—H420.9300
C15—H15A0.9700C43—C441.358 (10)
C15—H15B0.9700C43—C451.492 (8)
C16—N41.394 (10)C44—H440.9300
C16—C171.506 (8)C45—O61.214 (10)
C16—H16A0.9700C45—O51.304 (11)
C16—H16B0.9700C46—O91.246 (8)
C17—N31.452 (10)C46—O101.283 (9)
C17—H17A0.9700C46—C471.490 (10)
C17—H17B0.9700C47—C521.381 (9)
C18—N31.461 (8)C47—C481.382 (9)
C18—C191.503 (10)C48—C491.370 (10)
C18—H18A0.9700C48—H480.9300
C18—H18B0.9700C49—C501.351 (10)
C19—C201.376 (10)C49—C531.518 (10)
C19—C241.382 (10)C50—C511.372 (10)
C20—C211.379 (11)C50—H500.9300
C20—H200.9300C51—C521.385 (10)
C21—C221.372 (12)C51—H510.9300
C21—H210.9300C52—H520.9300
C22—C231.402 (12)C53—O121.239 (9)
C22—H220.9300C53—O111.253 (10)
C23—C241.371 (10)N1—H1N0.85 (6)
C23—H230.9300N2—H2N0.83 (2)
C24—O21.380 (9)N3—H3N0.82 (5)
C25—O21.420 (8)N4—H4N0.85 (6)
C25—C261.489 (10)O5—H5O0.85 (8)
C25—H25A0.9700O8—H8O0.87 (2)
C25—H25B0.9700
O11—Cd1—N293.5 (2)C29—C28—H28120.7
O11—Cd1—N3127.9 (2)C27—C28—H28120.7
N2—Cd1—N3135.4 (2)C30—C29—C28122.0 (9)
O11—Cd1—N4128.5 (2)C30—C29—H29119.0
N2—Cd1—N490.1 (2)C28—C29—H29119.0
N3—Cd1—N477.1 (2)C29—C30—C31119.4 (9)
O11—Cd1—N188.9 (2)C29—C30—H30120.3
N2—Cd1—N177.4 (2)C31—C30—H30120.3
N3—Cd1—N186.6 (2)C32—C31—C30121.3 (8)
N4—Cd1—N1141.5 (2)C32—C31—H31119.3
O11—Cd1—O1254.7 (2)C30—C31—H31119.3
N2—Cd1—O12135.87 (19)C31—C32—C27118.2 (7)
N3—Cd1—O1287.1 (2)C31—C32—C33121.7 (7)
N4—Cd1—O1289.0 (2)C27—C32—C33120.0 (7)
N1—Cd1—O12125.1 (2)N1—C33—C32112.7 (6)
C6—C1—C2118.1 (9)N1—C33—H33A109.0
C6—C1—C36121.7 (8)C32—C33—H33A109.0
C2—C1—C36120.1 (7)N1—C33—H33B109.0
C3—C2—C1120.2 (10)C32—C33—H33B109.0
C3—C2—H2119.9H33A—C33—H33B107.8
C1—C2—H2119.9N1—C34—C35111.3 (6)
C4—C3—C2119.6 (12)N1—C34—H34A109.4
C4—C3—H3120.2C35—C34—H34A109.4
C2—C3—H3120.2N1—C34—H34B109.4
C3—C4—C5121.7 (12)C35—C34—H34B109.4
C3—C4—H4119.2H34A—C34—H34B108.0
C5—C4—H4119.2N2—C35—C34111.8 (6)
C4—C5—C6117.8 (11)N2—C35—H35A109.3
C4—C5—H5121.1C34—C35—H35A109.3
C6—C5—H5121.1N2—C35—H35B109.3
C1—C6—O3115.9 (8)C34—C35—H35B109.3
C1—C6—C5122.4 (10)H35A—C35—H35B107.9
O3—C6—C5121.7 (9)N2—C36—C1113.7 (6)
O3—C7—C8113.3 (8)N2—C36—H36A108.8
O3—C7—H7A108.9C1—C36—H36A108.8
C8—C7—H7A108.9N2—C36—H36B108.8
O3—C7—H7B108.9C1—C36—H36B108.8
C8—C7—H7B108.9H36A—C36—H36B107.7
H7A—C7—H7B107.7O7—C38—O8124.1 (8)
O4—C8—C7109.5 (8)O7—C38—C39123.4 (8)
O4—C8—H8A109.8O8—C38—C39112.6 (8)
C7—C8—H8A109.8C44—C39—C40119.0 (7)
O4—C8—H8B109.8C44—C39—C38122.2 (7)
C7—C8—H8B109.8C40—C39—C38118.8 (7)
H8A—C8—H8B108.2C41—C40—C39118.4 (8)
C14—C9—O4115.9 (8)C41—C40—H40120.8
C14—C9—C10121.2 (11)C39—C40—H40120.8
O4—C9—C10123.0 (10)C40—C41—C42121.3 (8)
C11—C10—C9118.7 (12)C40—C41—H41119.3
C11—C10—H10120.7C42—C41—H41119.3
C9—C10—H10120.7C43—C42—C41120.0 (8)
C12—C11—C10120.5 (11)C43—C42—H42120.0
C12—C11—H11119.7C41—C42—H42120.0
C10—C11—H11119.7C44—C43—C42119.4 (8)
C11—C12—C13119.4 (12)C44—C43—C45119.2 (8)
C11—C12—H12120.3C42—C43—C45121.4 (8)
C13—C12—H12120.3C43—C44—C39122.0 (7)
C14—C13—C12122.4 (11)C43—C44—H44119.0
C14—C13—H13118.8C39—C44—H44119.0
C12—C13—H13118.8O6—C45—O5125.9 (8)
C13—C14—C9117.8 (8)O6—C45—C43121.5 (9)
C13—C14—C15123.1 (8)O5—C45—C43112.7 (9)
C9—C14—C15119.1 (8)O9—C46—O10124.3 (8)
N4—C15—C14113.5 (6)O9—C46—C47120.4 (7)
N4—C15—H15A108.9O10—C46—C47115.3 (7)
C14—C15—H15A108.9C52—C47—C48117.6 (7)
N4—C15—H15B108.9C52—C47—C46120.3 (7)
C14—C15—H15B108.9C48—C47—C46122.1 (7)
H15A—C15—H15B107.7C49—C48—C47121.5 (7)
N4—C16—C17117.0 (7)C49—C48—H48119.2
N4—C16—H16A108.1C47—C48—H48119.2
C17—C16—H16A108.1C50—C49—C48119.6 (7)
N4—C16—H16B108.1C50—C49—C53121.0 (8)
C17—C16—H16B108.1C48—C49—C53119.3 (8)
H16A—C16—H16B107.3C49—C50—C51121.2 (7)
N3—C17—C16112.8 (7)C49—C50—H50119.4
N3—C17—H17A109.0C51—C50—H50119.4
C16—C17—H17A109.0C50—C51—C52118.7 (8)
N3—C17—H17B109.0C50—C51—H51120.6
C16—C17—H17B109.0C52—C51—H51120.6
H17A—C17—H17B107.8C47—C52—C51121.3 (7)
N3—C18—C19113.5 (6)C47—C52—H52119.4
N3—C18—H18A108.9C51—C52—H52119.4
C19—C18—H18A108.9O12—C53—O11123.3 (8)
N3—C18—H18B108.9O12—C53—C49118.9 (9)
C19—C18—H18B108.9O11—C53—C49117.8 (8)
H18A—C18—H18B107.7O12—C53—Cd165.3 (4)
C20—C19—C24116.8 (7)O11—C53—Cd158.0 (4)
C20—C19—C18122.7 (7)C49—C53—Cd1174.5 (6)
C24—C19—C18120.5 (7)C27—O1—C26117.8 (6)
C19—C20—C21124.3 (8)C24—O2—C25118.1 (6)
C19—C20—H20117.8C7—O3—C6118.3 (7)
C21—C20—H20117.8C8—O4—C9120.1 (8)
C22—C21—C20117.1 (9)C53—O11—Cd194.5 (5)
C22—C21—H21121.4C53—O12—Cd187.4 (5)
C20—C21—H21121.4C34—N1—C33113.8 (6)
C21—C22—C23120.9 (8)C34—N1—Cd1104.0 (4)
C21—C22—H22119.6C33—N1—Cd1117.3 (4)
C23—C22—H22119.6C34—N1—H1N105 (5)
C24—C23—C22119.3 (8)C33—N1—H1N112 (5)
C24—C23—H23120.3Cd1—N1—H1N104 (5)
C22—C23—H23120.3C36—N2—C35113.3 (6)
C23—C24—O2124.0 (7)C36—N2—Cd1118.0 (4)
C23—C24—C19121.6 (8)C35—N2—Cd1106.4 (4)
O2—C24—C19114.4 (7)C36—N2—H2N110 (5)
O2—C25—C26108.2 (6)C35—N2—H2N105 (5)
O2—C25—H25A110.1Cd1—N2—H2N103 (5)
C26—C25—H25A110.1C17—N3—C18108.4 (6)
O2—C25—H25B110.1C17—N3—Cd1107.8 (5)
C26—C25—H25B110.1C18—N3—Cd1112.8 (4)
H25A—C25—H25B108.4C17—N3—H3N112 (5)
O1—C26—C25109.5 (7)C18—N3—H3N110 (5)
O1—C26—H26A109.8Cd1—N3—H3N106 (5)
C25—C26—H26A109.8C16—N4—C15116.7 (7)
O1—C26—H26B109.8C16—N4—Cd1106.7 (4)
C25—C26—H26B109.8C15—N4—Cd1114.6 (4)
H26A—C26—H26B108.2C16—N4—H4N116 (5)
O1—C27—C32116.3 (7)C15—N4—H4N99 (5)
O1—C27—C28123.2 (7)Cd1—N4—H4N102 (5)
C32—C27—C28120.4 (8)C45—O5—H5O105 (8)
C29—C28—C27118.5 (8)C38—O8—H8O107 (7)
C6—C1—C2—C3−0.4 (13)N1—Cd1—C53—O12−134.0 (4)
C36—C1—C2—C3177.5 (8)N2—Cd1—C53—O11−35.7 (5)
C1—C2—C3—C4−1.8 (16)N3—Cd1—C53—O11140.9 (5)
C2—C3—C4—C54.2 (18)N4—Cd1—C53—O11−136.5 (5)
C3—C4—C5—C6−4.2 (17)N1—Cd1—C53—O1148.8 (5)
C2—C1—C6—O3178.8 (7)O12—Cd1—C53—O11−177.2 (8)
C36—C1—C6—O30.9 (11)C32—C27—O1—C26140.3 (7)
C2—C1—C6—C50.3 (12)C28—C27—O1—C26−42.5 (10)
C36—C1—C6—C5−177.6 (7)C25—C26—O1—C27175.0 (6)
C4—C5—C6—C11.9 (14)C23—C24—O2—C25−12.8 (11)
C4—C5—C6—O3−176.5 (9)C19—C24—O2—C25168.9 (6)
O3—C7—C8—O449.9 (13)C26—C25—O2—C24−179.4 (6)
C14—C9—C10—C111.2 (15)C8—C7—O3—C6−175.5 (9)
O4—C9—C10—C11−179.2 (9)C1—C6—O3—C7137.9 (9)
C9—C10—C11—C120.4 (17)C5—C6—O3—C7−43.6 (13)
C10—C11—C12—C13−1.1 (18)C7—C8—O4—C9171.2 (8)
C11—C12—C13—C140.1 (15)C14—C9—O4—C8163.9 (9)
C12—C13—C14—C91.5 (13)C10—C9—O4—C8−15.7 (14)
C12—C13—C14—C15−176.5 (8)O12—C53—O11—Cd1−3.1 (8)
O4—C9—C14—C13178.3 (7)C49—C53—O11—Cd1176.0 (5)
C10—C9—C14—C13−2.2 (13)N2—Cd1—O11—C53148.4 (5)
O4—C9—C14—C15−3.6 (11)N3—Cd1—O11—C53−49.4 (6)
C10—C9—C14—C15175.9 (8)N4—Cd1—O11—C5355.5 (6)
C13—C14—C15—N4108.1 (9)N1—Cd1—O11—C53−134.2 (5)
C9—C14—C15—N4−69.9 (9)O12—Cd1—O11—C531.6 (4)
N4—C16—C17—N3−52.6 (13)O11—C53—O12—Cd12.9 (8)
N3—C18—C19—C20−101.1 (8)C49—C53—O12—Cd1−176.2 (6)
N3—C18—C19—C2481.9 (9)O11—Cd1—O12—C53−1.6 (4)
C24—C19—C20—C210.5 (12)N2—Cd1—O12—C53−53.2 (5)
C18—C19—C20—C21−176.6 (8)N3—Cd1—O12—C53140.5 (5)
C19—C20—C21—C220.9 (13)N4—Cd1—O12—C53−142.4 (5)
C20—C21—C22—C23−0.9 (14)N1—Cd1—O12—C5356.7 (5)
C21—C22—C23—C24−0.5 (13)C35—C34—N1—C33−85.7 (7)
C22—C23—C24—O2−176.2 (7)C35—C34—N1—Cd143.0 (6)
C22—C23—C24—C192.1 (12)C32—C33—N1—C34−53.0 (8)
C20—C19—C24—C23−2.0 (11)C32—C33—N1—Cd1−174.6 (5)
C18—C19—C24—C23175.1 (7)O11—Cd1—N1—C34−108.0 (5)
C20—C19—C24—O2176.4 (6)N2—Cd1—N1—C34−14.1 (4)
C18—C19—C24—O2−6.5 (10)N3—Cd1—N1—C34124.0 (4)
O2—C25—C26—O156.7 (8)N4—Cd1—N1—C3459.7 (6)
O1—C27—C28—C29−176.8 (7)O12—Cd1—N1—C34−152.0 (4)
C32—C27—C28—C290.3 (11)C53—Cd1—N1—C34−128.3 (5)
C27—C28—C29—C302.4 (13)O11—Cd1—N1—C3318.6 (5)
C28—C29—C30—C31−2.4 (15)N2—Cd1—N1—C33112.5 (5)
C29—C30—C31—C32−0.3 (14)N3—Cd1—N1—C33−109.4 (5)
C30—C31—C32—C272.9 (12)N4—Cd1—N1—C33−173.7 (4)
C30—C31—C32—C33−172.6 (8)O12—Cd1—N1—C33−25.4 (6)
O1—C27—C32—C31174.4 (7)C53—Cd1—N1—C33−1.7 (6)
C28—C27—C32—C31−2.9 (11)C1—C36—N2—C3567.6 (8)
O1—C27—C32—C33−10.0 (10)C1—C36—N2—Cd1−167.2 (5)
C28—C27—C32—C33172.7 (6)C34—C35—N2—C36177.0 (6)
C31—C32—C33—N1108.6 (8)C34—C35—N2—Cd145.8 (6)
C27—C32—C33—N1−66.9 (9)O11—Cd1—N2—C36−56.5 (5)
N1—C34—C35—N2−64.3 (8)N3—Cd1—N2—C36143.7 (4)
C6—C1—C36—N283.3 (8)N4—Cd1—N2—C3672.0 (5)
C2—C1—C36—N2−94.5 (8)N1—Cd1—N2—C36−144.6 (5)
O7—C38—C39—C44−164.4 (8)O12—Cd1—N2—C36−16.7 (6)
O8—C38—C39—C4415.6 (11)C53—Cd1—N2—C36−40.9 (5)
O7—C38—C39—C4016.9 (13)O11—Cd1—N2—C3572.1 (4)
O8—C38—C39—C40−163.2 (7)N3—Cd1—N2—C35−87.7 (5)
C44—C39—C40—C410.2 (11)N4—Cd1—N2—C35−159.4 (4)
C38—C39—C40—C41179.1 (8)N1—Cd1—N2—C35−16.0 (4)
C39—C40—C41—C42−0.9 (13)O12—Cd1—N2—C35111.9 (4)
C40—C41—C42—C431.0 (13)C53—Cd1—N2—C3587.7 (4)
C41—C42—C43—C44−0.4 (12)C16—C17—N3—C18159.4 (8)
C41—C42—C43—C45179.3 (8)C16—C17—N3—Cd137.0 (10)
C42—C43—C44—C39−0.4 (12)C19—C18—N3—C1770.6 (8)
C45—C43—C44—C39180.0 (7)C19—C18—N3—Cd1−170.1 (5)
C40—C39—C44—C430.4 (11)O11—Cd1—N3—C17114.7 (6)
C38—C39—C44—C43−178.4 (7)N2—Cd1—N3—C17−91.1 (6)
C44—C43—C45—O65.1 (13)N4—Cd1—N3—C17−14.4 (6)
C42—C43—C45—O6−174.6 (9)N1—Cd1—N3—C17−159.3 (6)
C44—C43—C45—O5−174.3 (8)O12—Cd1—N3—C1775.3 (6)
C42—C43—C45—O56.0 (11)C53—Cd1—N3—C1793.1 (6)
O9—C46—C47—C52−33.8 (10)O11—Cd1—N3—C18−4.9 (6)
O10—C46—C47—C52145.5 (7)N2—Cd1—N3—C18149.3 (4)
O9—C46—C47—C48147.6 (7)N4—Cd1—N3—C18−134.0 (5)
O10—C46—C47—C48−33.0 (10)N1—Cd1—N3—C1881.1 (5)
C52—C47—C48—C491.0 (10)O12—Cd1—N3—C18−44.3 (4)
C46—C47—C48—C49179.6 (6)C53—Cd1—N3—C18−26.5 (5)
C47—C48—C49—C50−1.1 (10)C17—C16—N4—C15−94.1 (9)
C47—C48—C49—C53178.7 (6)C17—C16—N4—Cd135.4 (10)
C48—C49—C50—C510.1 (11)C14—C15—N4—C16−51.4 (9)
C53—C49—C50—C51−179.7 (7)C14—C15—N4—Cd1−177.1 (5)
C49—C50—C51—C520.9 (11)O11—Cd1—N4—C16−139.1 (6)
C48—C47—C52—C510.0 (10)N2—Cd1—N4—C16126.3 (6)
C46—C47—C52—C51−178.6 (7)N3—Cd1—N4—C16−10.5 (6)
C50—C51—C52—C47−1.0 (11)N1—Cd1—N4—C1656.7 (7)
C50—C49—C53—O12−1.0 (10)O12—Cd1—N4—C16−97.8 (6)
C48—C49—C53—O12179.2 (6)C53—Cd1—N4—C16−115.1 (6)
C50—C49—C53—O11179.9 (7)O11—Cd1—N4—C15−8.3 (6)
C48—C49—C53—O110.1 (10)N2—Cd1—N4—C15−102.9 (5)
O11—Cd1—C53—O12177.2 (8)N3—Cd1—N4—C15120.2 (5)
N2—Cd1—C53—O12141.4 (4)N1—Cd1—N4—C15−172.5 (4)
N3—Cd1—C53—O12−41.9 (5)O12—Cd1—N4—C1533.0 (5)
N4—Cd1—C53—O1240.6 (5)C53—Cd1—N4—C1515.7 (6)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N3—H3N···O80.82 (5)2.42 (4)3.148 (8)147 (6)
N4—H4N···O40.85 (6)2.46 (6)3.043 (8)127 (6)
N2—H2N···O9i0.83 (2)2.10 (3)2.901 (7)163 (6)
O8—H8O···O9i0.87 (2)1.76 (3)2.605 (7)166 (9)
O5—H5O···O10ii0.85 (8)1.71 (8)2.548 (9)170 (12)

Symmetry codes: (i) −x+3/2, y−1/2, −z+3/2; (ii) x+1/2, −y+3/2, z−1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HY2157).

References

  • Banerjee, S., Lassahn, P., Janiak, C. & Ghosh, A. (2005). Polyhedron, 24, 2963–2971.
  • Brandenburg, K. (1999). DIAMOND Crystal Impact GbR, Bonn, Germany.
  • Higashi, T. (1995). ABSCOR Rigaku Corporation, Tokyo, Japan.
  • Liu, Q., Li, Y., Liu, H., Wang, F. & Xu, Z. (2005). J. Mol. Struct.733, 25–28.
  • Rigaku (1998). PROCESS-AUTO Rigaku Corporation, Tokyo, Japan.
  • Sarkar, B., Drew, M. G., Estrader, M., Diaz, C. & Ghosh, A. (2008). Polyhedron, 27, 2625–2633.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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