Bis[2-hydr­oxy-N′-(2-hydroxy­benzo­yl)benzohydrazitato]dipyridine­cadmium(II)

Chen, Y.-T.; Li, D.-C.

doi:10.1107/S1600536808034533

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 11| November 2008| Page m1466

doi:10.1107/S1600536808034533

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Bis[2-hydroxy-N′-(2-hydroxybenzoyl)benzohydrazitato]dipyridinecadmium(II)

Yu-Ting Chen ^a,^b and Da-Cheng Li ^b ^*

^aDepartment of Chemistry, Dezhou University, Dezhou 253023, People's Republic of China, and ^bCollege of Chemistry and Chemical Engineering, Liaocheng University, Liaocheng 252059, People's Republic of China
^*Correspondence e-mail: lidacheng@lcu.edu.cn

(Received 8 August 2008; accepted 22 October 2008; online 31 October 2008)

The title complex, [Cd(C₁₄H₁₁N₂O₄)₂(C₅H₅N)₂], exhibits crystallographic twofold symmetry. The Cd^II atom is located on the twofold rotation axis and reveals a slightly distorted octahedral coordination defined by four atoms (N₂O₂) from two symmetry-related chelate ligands and two pyridine N atoms. Intramolecular O—H⋯O and N—H⋯O hydrogen bonds stabilize the molecular conformation while intermolecular O—H⋯O hydrogen bonding links molecules into a triad, generating a helix along the threefold screw axis.

Related literature

Three manganese metallacrowns with unsymmetrical aroylhydrazine ligands were synthesized and reported by Dou et al. (2006 ) and John et al. (2006 ). For the crystal structure of an iron compound with N,N′-bis-picolinoyl hydrazine, see: Bernhardt et al. (2005 ). For a nickel complex formed by N,N′-disalicyloylhydrazine, see: Chen et al. (2007 ).

Experimental

Crystal data

[Cd(C₁₄H₁₁N₂O₄)₂(C₅H₅N)₂]
M_r = 813.10
Trigonal, P 3₁ 21
a = 13.0380 (10) Å
c = 18.069 (3) Å
V = 2660.0 (5) Å³
Z = 3
Mo Kα radiation
μ = 0.68 mm⁻¹
T = 298 (2) K
0.40 × 0.38 × 0.35 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.773, T_max = 0.797
13955 measured reflections
3146 independent reflections
2750 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.027
wR(F²) = 0.071
S = 1.00
3146 reflections
241 parameters
H-atom parameters constrained
Δρ_max = 0.90 e Å⁻³
Δρ_min = −0.32 e Å⁻³
Absolute structure: Flack (1983 ), 1353 Friedel pairs
Flack parameter: −0.06 (3)

Table 1
Selected bond lengths (Å)

Cd1—N1	2.331 (3)
Cd1—N3	2.337 (3)
Cd1—O1	2.389 (2)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4⋯O3	0.82	1.92	2.638 (4)	145
N2—H2⋯O2	0.86	1.94	2.624 (4)	135
O2—H2A⋯O3ⁱ	0.82	1.88	2.639 (3)	153
Symmetry code: (i) $[x-y, -y, -z+{\script{5\over 3}}]$ .

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808034533/kp2188sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808034533/kp2188Isup2.hkl

checkCIF report

Comment top

Metal complexes with aroylhydrazine ligands are of increasing attention due to their interesting chemical activities (John et al. 2006; Dou et al., 2006). However, the research on the compounds with symmetrical diaroylhydrazine ligands was limited (Bernhardt et al., 2005; Chen et al., 2007). As an extension of our work on the structural characterization of these compounds, the title complex, (I), is synthesized and characterized by X-ray structure analysis. The complex (I) exhibits a twofold rotation symmetry. It comprises of one Cd^II atom at special position at the twofold rotation axes coordinated by two ligands and two pyridines (Fig. 1 and Table 1). Each ligand acts as the bidentate via the iminoacyl groups forming two five-membered rings around metal ion with the dihedral angle of 59.71 (4)°.

Intramolecular O4—H4···O3 and N2—H2···O2 hydrogen bonds stabilizes the molecular conformation. There is also an intermolecular hydrogen bond O—H···O hydrogen bond [ 2.639 (3) Å] (Table 2) assembling three molecules into a triad, that is a basic structural element of a helix along [0 0 1] direction (Fig. 2).

Related literature top

Three manganese metallacrowns with unsymmetrical aroylhydrazine ligands were synthesized and reported by Dou et al. (2006) and John et al. (2006). For the crystal structure of an iron compound with N,N'-bis-picolinoyl hydrazine, see: Bernhardt et al. (2005). For a nickel complex formed by N,N'-disalicyloylhydrazine reported by Chen et al. (2007).

Experimental top

The solution of Cd(NO₃)₂4H₂O (0.123 g, 0.4 mmol) in methanol (10 mL) was added to the mixture of 1,2-disalicyloylhydrazine (0.054 g, 0.2 mmol) and sodium hydroxide (0.032 g, 0.8 mmol) in pyridine (10 mL). A colourless solution was generated after stirring for two hours at room temperature. The solution was allowed to stand for 2 weeks, whereupon white block crystals were obtained. Yield: 0.058 g, 77%. m. p.> 573 K. Anal. for C₃₈H₃₂CdN₆O₈: Calc. C, 56.08; H, 3.93; N, 10.33; Found: C, 56.54; H, 3.71; N, 10.54%. The No. of CCDC: 686345.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SMART (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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

	Fig. 1. The molecular structure of the title complex. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. Supramolecular structure of the title complex in the direction [001].

Bis[2-hydroxy-N'-(2-hydroxybenzoyl)benzohydrazitato]dipyridinecadmium(II) top

Crystal data top

[Cd(C₁₄H₁₁N₂O₄)₂(C₅H₅N)₂]	D_x = 1.523 Mg m⁻³
M_r = 813.10	Mo Kα radiation, λ = 0.71073 Å
Trigonal, P3₁21	Cell parameters from 5141 reflections
a = 13.038 (1) Å	θ = 2.9–22.9°
c = 18.069 (3) Å	µ = 0.68 mm⁻¹
V = 2660.0 (5) Å³	T = 298 K
Z = 3	Block, colourless
F(000) = 1242	0.40 × 0.38 × 0.35 mm

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	3146 independent reflections
Radiation source: fine-focus sealed tube	2750 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→15
T_min = 0.773, T_max = 0.797	k = −15→15
13955 measured reflections	l = −21→10

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.027	H-atom parameters constrained
wR(F²) = 0.071	w = 1/[σ²(F_o²) + (0.041P)² + 0.5675P] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max < 0.001
3146 reflections	Δρ_max = 0.90 e Å⁻³
241 parameters	Δρ_min = −0.32 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1353 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.06 (3)

Crystal data top

[Cd(C₁₄H₁₁N₂O₄)₂(C₅H₅N)₂]	Z = 3
M_r = 813.10	Mo Kα radiation
Trigonal, P3₁21	µ = 0.68 mm⁻¹
a = 13.038 (1) Å	T = 298 K
c = 18.069 (3) Å	0.40 × 0.38 × 0.35 mm
V = 2660.0 (5) Å³

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	3146 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2750 reflections with I > 2σ(I)
T_min = 0.773, T_max = 0.797	R_int = 0.033
13955 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.027	H-atom parameters constrained
wR(F²) = 0.071	Δρ_max = 0.90 e Å⁻³
S = 1.00	Δρ_min = −0.32 e Å⁻³
3146 reflections	Absolute structure: Flack (1983), 1353 Friedel pairs
241 parameters	Absolute structure parameter: −0.06 (3)
0 restraints

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

	x	y	z	U_iso*/U_eq
Cd1	1.0000	0.45722 (2)	0.6667	0.04088 (11)
N1	0.8620 (2)	0.2612 (2)	0.69499 (15)	0.0387 (7)
N2	0.8356 (3)	0.2467 (3)	0.77051 (14)	0.0406 (6)
H2	0.8005	0.1771	0.7897	0.049*
N3	0.8726 (2)	0.5186 (3)	0.61934 (16)	0.0449 (7)
O1	0.9119 (2)	0.4418 (2)	0.78506 (13)	0.0517 (7)
O2	0.7567 (3)	0.1137 (2)	0.88928 (14)	0.0584 (7)
H2A	0.7290	0.0561	0.9170	0.088*
O3	0.8013 (3)	0.06392 (19)	0.69676 (12)	0.0558 (6)
O4	0.9060 (3)	0.0079 (3)	0.59233 (16)	0.0797 (10)
H4	0.8760	0.0022	0.6331	0.120*
C1	0.8648 (3)	0.3405 (3)	0.81227 (18)	0.0391 (8)
C2	0.8409 (3)	0.3228 (3)	0.89327 (19)	0.0403 (8)
C3	0.7918 (3)	0.2136 (4)	0.9296 (2)	0.0454 (9)
C4	0.7786 (4)	0.2086 (4)	1.0058 (2)	0.0548 (10)
H4A	0.7467	0.1360	1.0298	0.066*
C5	0.8122 (4)	0.3102 (4)	1.0464 (2)	0.0614 (11)
H5	0.8012	0.3053	1.0974	0.074*
C6	0.8618 (4)	0.4184 (4)	1.0120 (2)	0.0556 (10)
H6	0.8858	0.4872	1.0393	0.067*
C7	0.8753 (3)	0.4233 (3)	0.9357 (2)	0.0477 (9)
H7	0.9085	0.4965	0.9123	0.057*
C8	0.8396 (3)	0.1621 (3)	0.66318 (18)	0.0402 (8)
C9	0.8647 (3)	0.1680 (3)	0.58281 (18)	0.0415 (8)
C10	0.9002 (4)	0.0938 (4)	0.5519 (2)	0.0547 (10)
C11	0.9321 (4)	0.1039 (4)	0.4769 (2)	0.0687 (13)
H11	0.9592	0.0562	0.4568	0.082*
C12	0.9225 (4)	0.1852 (4)	0.4338 (2)	0.0673 (12)
H12	0.9435	0.1926	0.3841	0.081*
C13	0.8832 (4)	0.2547 (4)	0.4624 (2)	0.0629 (12)
H13	0.8754	0.3080	0.4320	0.075*
C14	0.8542 (3)	0.2472 (4)	0.5364 (2)	0.0516 (9)
H14	0.8274	0.2958	0.5555	0.062*
C15	0.9145 (4)	0.6185 (4)	0.5806 (2)	0.0550 (10)
H15	0.9942	0.6587	0.5675	0.066*
C16	0.8437 (4)	0.6645 (4)	0.5591 (2)	0.0636 (12)
H16	0.8760	0.7358	0.5334	0.076*
C17	0.7270 (4)	0.6045 (4)	0.5759 (2)	0.0627 (12)
H17	0.6777	0.6335	0.5616	0.075*
C18	0.6827 (3)	0.5002 (4)	0.6144 (2)	0.0591 (11)
H18	0.6026	0.4570	0.6263	0.071*
C19	0.7572 (3)	0.4610 (3)	0.6349 (2)	0.0535 (9)
H19	0.7262	0.3903	0.6612	0.064*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cd1	0.0445 (2)	0.03796 (14)	0.04239 (18)	0.02224 (11)	0.00869 (17)	0.00434 (9)
N1	0.0392 (17)	0.0368 (16)	0.0340 (15)	0.0144 (14)	0.0019 (12)	0.0033 (12)
N2	0.0437 (16)	0.0396 (16)	0.0347 (15)	0.0179 (13)	0.0072 (13)	0.0058 (14)
N3	0.0448 (18)	0.0430 (17)	0.0494 (17)	0.0236 (15)	0.0064 (13)	0.0045 (14)
O1	0.0692 (18)	0.0398 (14)	0.0459 (15)	0.0271 (13)	0.0147 (13)	0.0067 (12)
O2	0.080 (2)	0.0438 (15)	0.0434 (15)	0.0254 (14)	0.0077 (13)	0.0107 (13)
O3	0.0734 (19)	0.0376 (13)	0.0493 (14)	0.0223 (15)	0.0222 (15)	0.0080 (11)
O4	0.118 (3)	0.081 (2)	0.066 (2)	0.070 (2)	0.0278 (19)	0.0082 (17)
C1	0.0388 (19)	0.041 (2)	0.041 (2)	0.0226 (17)	0.0035 (16)	0.0036 (17)
C2	0.042 (2)	0.049 (2)	0.0364 (18)	0.0282 (17)	0.0029 (15)	0.0027 (16)
C3	0.044 (2)	0.056 (2)	0.042 (2)	0.0290 (18)	0.0009 (16)	0.0031 (18)
C4	0.065 (3)	0.066 (3)	0.042 (2)	0.040 (2)	0.0030 (19)	0.012 (2)
C5	0.074 (3)	0.092 (4)	0.037 (2)	0.055 (3)	0.005 (2)	0.006 (2)
C6	0.064 (3)	0.073 (3)	0.048 (2)	0.048 (2)	−0.0070 (19)	−0.011 (2)
C7	0.055 (2)	0.049 (2)	0.049 (2)	0.0344 (19)	0.0047 (17)	0.0020 (17)
C8	0.0341 (18)	0.0382 (17)	0.0420 (17)	0.0133 (15)	0.0033 (15)	0.0030 (14)
C9	0.038 (2)	0.0391 (17)	0.0363 (16)	0.0113 (17)	0.0027 (16)	−0.0017 (13)
C10	0.063 (3)	0.049 (2)	0.047 (2)	0.025 (2)	0.005 (2)	−0.0025 (18)
C11	0.077 (3)	0.076 (3)	0.046 (2)	0.033 (3)	0.011 (2)	−0.011 (2)
C12	0.065 (3)	0.073 (3)	0.039 (2)	0.016 (2)	0.004 (2)	−0.006 (2)
C13	0.065 (3)	0.061 (2)	0.040 (2)	0.014 (2)	−0.010 (2)	0.0026 (18)
C14	0.047 (2)	0.044 (2)	0.050 (2)	0.0129 (17)	−0.0035 (18)	−0.0011 (19)
C15	0.050 (2)	0.056 (2)	0.060 (3)	0.027 (2)	0.0090 (18)	0.012 (2)
C16	0.069 (3)	0.067 (3)	0.062 (2)	0.040 (2)	0.007 (2)	0.025 (2)
C17	0.065 (3)	0.088 (3)	0.053 (2)	0.051 (3)	−0.006 (2)	0.002 (2)
C18	0.041 (2)	0.074 (3)	0.062 (3)	0.028 (2)	−0.0012 (19)	−0.007 (2)
C19	0.048 (2)	0.044 (2)	0.063 (2)	0.0198 (19)	0.0099 (19)	0.0037 (19)

Geometric parameters (Å, º) top

Cd1—N1	2.331 (3)	C5—H5	0.9300
Cd1—N1ⁱ	2.331 (3)	C6—C7	1.387 (5)
Cd1—N3ⁱ	2.337 (3)	C6—H6	0.9300
Cd1—N3	2.337 (3)	C7—H7	0.9300
Cd1—O1	2.389 (2)	C8—C9	1.482 (4)
Cd1—O1ⁱ	2.389 (2)	C9—C10	1.382 (5)
N1—C8	1.307 (4)	C9—C14	1.389 (5)
N1—N2	1.397 (4)	C10—C11	1.404 (5)
N2—C1	1.320 (4)	C11—C12	1.371 (6)
N2—H2	0.8600	C11—H11	0.9300
N3—C15	1.332 (5)	C12—C13	1.346 (6)
N3—C19	1.333 (5)	C12—H12	0.9300
O1—C1	1.245 (4)	C13—C14	1.380 (5)
O2—C3	1.357 (4)	C13—H13	0.9300
O2—H2A	0.8200	C14—H14	0.9300
O3—C8	1.271 (4)	C15—C16	1.385 (6)
O4—C10	1.371 (5)	C15—H15	0.9300
O4—H4	0.8200	C16—C17	1.352 (6)
C1—C2	1.490 (5)	C16—H16	0.9300
C2—C7	1.385 (5)	C17—C18	1.372 (6)
C2—C3	1.399 (5)	C17—H17	0.9300
C3—C4	1.384 (5)	C18—C19	1.356 (6)
C4—C5	1.380 (6)	C18—H18	0.9300
C4—H4A	0.9300	C19—H19	0.9300
C5—C6	1.372 (6)

N1—Cd1—N1ⁱ	89.45 (14)	C5—C6—C7	118.8 (4)
N1—Cd1—N3ⁱ	145.80 (9)	C5—C6—H6	120.6
N1ⁱ—Cd1—N3ⁱ	99.48 (10)	C7—C6—H6	120.6
N1—Cd1—N3	99.48 (10)	C2—C7—C6	122.2 (4)
N1ⁱ—Cd1—N3	145.80 (9)	C2—C7—H7	118.9
N3ⁱ—Cd1—N3	91.48 (14)	C6—C7—H7	118.9
N1—Cd1—O1	68.64 (9)	O3—C8—N1	124.5 (3)
N1ⁱ—Cd1—O1	125.88 (9)	O3—C8—C9	119.0 (3)
N3ⁱ—Cd1—O1	79.62 (9)	N1—C8—C9	116.4 (3)
N3—Cd1—O1	87.84 (9)	C10—C9—C14	117.9 (3)
N1—Cd1—O1ⁱ	125.88 (9)	C10—C9—C8	120.1 (3)
N1ⁱ—Cd1—O1ⁱ	68.64 (9)	C14—C9—C8	121.9 (3)
N3ⁱ—Cd1—O1ⁱ	87.84 (9)	O4—C10—C9	122.1 (3)
N3—Cd1—O1ⁱ	79.62 (9)	O4—C10—C11	117.1 (4)
O1—Cd1—O1ⁱ	162.04 (12)	C9—C10—C11	120.7 (4)
C8—N1—N2	112.2 (3)	C12—C11—C10	118.9 (4)
C8—N1—Cd1	131.0 (2)	C12—C11—H11	120.5
N2—N1—Cd1	111.44 (19)	C10—C11—H11	120.5
C1—N2—N1	119.7 (3)	C13—C12—C11	121.0 (4)
C1—N2—H2	120.1	C13—C12—H12	119.5
N1—N2—H2	120.1	C11—C12—H12	119.5
C15—N3—C19	117.2 (3)	C12—C13—C14	120.4 (4)
C15—N3—Cd1	120.9 (2)	C12—C13—H13	119.8
C19—N3—Cd1	121.7 (2)	C14—C13—H13	119.8
C1—O1—Cd1	113.9 (2)	C13—C14—C9	120.9 (4)
C3—O2—H2A	109.5	C13—C14—H14	119.6
C10—O4—H4	109.5	C9—C14—H14	119.6
O1—C1—N2	121.1 (3)	N3—C15—C16	122.3 (4)
O1—C1—C2	120.4 (3)	N3—C15—H15	118.8
N2—C1—C2	118.5 (3)	C16—C15—H15	118.8
C7—C2—C3	118.0 (3)	C17—C16—C15	119.2 (4)
C7—C2—C1	117.0 (3)	C17—C16—H16	120.4
C3—C2—C1	124.9 (3)	C15—C16—H16	120.4
O2—C3—C4	121.0 (4)	C16—C17—C18	118.8 (4)
O2—C3—C2	119.2 (3)	C16—C17—H17	120.6
C4—C3—C2	119.8 (4)	C18—C17—H17	120.6
C5—C4—C3	120.8 (4)	C19—C18—C17	119.1 (4)
C5—C4—H4A	119.6	C19—C18—H18	120.5
C3—C4—H4A	119.6	C17—C18—H18	120.5
C6—C5—C4	120.4 (4)	N3—C19—C18	123.3 (4)
C6—C5—H5	119.8	N3—C19—H19	118.3
C4—C5—H5	119.8	C18—C19—H19	118.3

N1ⁱ—Cd1—N1—C8	−39.3 (3)	C7—C2—C3—C4	0.2 (5)
N3ⁱ—Cd1—N1—C8	−145.5 (3)	C1—C2—C3—C4	177.0 (4)
N3—Cd1—N1—C8	107.5 (3)	O2—C3—C4—C5	−178.7 (4)
O1—Cd1—N1—C8	−168.6 (3)	C2—C3—C4—C5	0.7 (6)
O1ⁱ—Cd1—N1—C8	23.6 (3)	C3—C4—C5—C6	−1.4 (6)
N1ⁱ—Cd1—N1—N2	112.3 (2)	C4—C5—C6—C7	1.2 (6)
N3ⁱ—Cd1—N1—N2	6.1 (3)	C3—C2—C7—C6	−0.4 (5)
N3—Cd1—N1—N2	−100.9 (2)	C1—C2—C7—C6	−177.5 (3)
O1—Cd1—N1—N2	−17.02 (19)	C5—C6—C7—C2	−0.3 (6)
O1ⁱ—Cd1—N1—N2	175.09 (18)	N2—N1—C8—O3	−1.8 (5)
C8—N1—N2—C1	172.8 (3)	Cd1—N1—C8—O3	149.6 (3)
Cd1—N1—N2—C1	15.7 (3)	N2—N1—C8—C9	180.0 (3)
N1—Cd1—N3—C15	−164.9 (3)	Cd1—N1—C8—C9	−28.6 (4)
N1ⁱ—Cd1—N3—C15	−61.7 (4)	O3—C8—C9—C10	−30.0 (5)
N3ⁱ—Cd1—N3—C15	47.6 (3)	N1—C8—C9—C10	148.3 (3)
O1—Cd1—N3—C15	127.1 (3)	O3—C8—C9—C14	150.3 (4)
O1ⁱ—Cd1—N3—C15	−39.9 (3)	N1—C8—C9—C14	−31.4 (5)
N1—Cd1—N3—C19	20.6 (3)	C14—C9—C10—O4	−175.9 (4)
N1ⁱ—Cd1—N3—C19	123.8 (3)	C8—C9—C10—O4	4.4 (6)
N3ⁱ—Cd1—N3—C19	−126.9 (3)	C14—C9—C10—C11	4.1 (6)
O1—Cd1—N3—C19	−47.3 (3)	C8—C9—C10—C11	−175.6 (4)
O1ⁱ—Cd1—N3—C19	145.6 (3)	O4—C10—C11—C12	177.2 (4)
N1—Cd1—O1—C1	19.5 (2)	C9—C10—C11—C12	−2.9 (7)
N1ⁱ—Cd1—O1—C1	−53.3 (3)	C10—C11—C12—C13	−0.1 (7)
N3ⁱ—Cd1—O1—C1	−147.5 (3)	C11—C12—C13—C14	1.6 (7)
N3—Cd1—O1—C1	120.5 (2)	C12—C13—C14—C9	−0.2 (6)
O1ⁱ—Cd1—O1—C1	166.0 (2)	C10—C9—C14—C13	−2.6 (5)
Cd1—O1—C1—N2	−19.3 (4)	C8—C9—C14—C13	177.1 (3)
Cd1—O1—C1—C2	160.3 (2)	C19—N3—C15—C16	2.3 (6)
N1—N2—C1—O1	2.6 (5)	Cd1—N3—C15—C16	−172.4 (3)
N1—N2—C1—C2	−177.0 (3)	N3—C15—C16—C17	−2.1 (6)
O1—C1—C2—C7	−1.1 (5)	C15—C16—C17—C18	0.6 (6)
N2—C1—C2—C7	178.5 (3)	C16—C17—C18—C19	0.5 (6)
O1—C1—C2—C3	−178.0 (3)	C15—N3—C19—C18	−1.2 (6)
N2—C1—C2—C3	1.6 (5)	Cd1—N3—C19—C18	173.5 (3)
C7—C2—C3—O2	179.6 (3)	C17—C18—C19—N3	−0.2 (7)
C1—C2—C3—O2	−3.5 (5)

Symmetry code: (i) −x+2, −x+y+1, −z+4/3.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O3	0.82	1.92	2.638 (4)	145
N2—H2···O2	0.86	1.94	2.624 (4)	135
O2—H2A···O3ⁱⁱ	0.82	1.88	2.639 (3)	153

Symmetry code: (ii) x−y, −y, −z+5/3.

Experimental details

Crystal data
Chemical formula	[Cd(C₁₄H₁₁N₂O₄)₂(C₅H₅N)₂]
M_r	813.10
Crystal system, space group	Trigonal, P3₁21
Temperature (K)	298
a, c (Å)	13.038 (1), 18.069 (3)
V (Å³)	2660.0 (5)
Z	3
Radiation type	Mo Kα
µ (mm⁻¹)	0.68
Crystal size (mm)	0.40 × 0.38 × 0.35

Data collection
Diffractometer	Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.773, 0.797
No. of measured, independent and observed [I > 2σ(I)] reflections	13955, 3146, 2750
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.027, 0.071, 1.00
No. of reflections	3146
No. of parameters	241
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.90, −0.32
Absolute structure	Flack (1983), 1353 Friedel pairs
Absolute structure parameter	−0.06 (3)

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Cd1—N1	2.331 (3)	O1—C1	1.245 (4)
Cd1—N3	2.337 (3)	O2—C3	1.357 (4)
Cd1—O1	2.389 (2)	O3—C8	1.271 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O3	0.82	1.92	2.638 (4)	144.9
N2—H2···O2	0.86	1.94	2.624 (4)	135.3
O2—H2A···O3ⁱ	0.82	1.88	2.639 (3)	152.7

Symmetry code: (i) x−y, −y, −z+5/3.

Acknowledgements

The authors acknowledge the support of the National Natural Science Foundation of China (grant No. 20671048).

References

Bernhardt, P. V., Chin, P., Sharpe, P. C., Wang, J. C. & Richardson, D. R. (2005). Biol. Inorg. Chem. 10, 761–777. Web of Science CSD CrossRef CAS Google Scholar
Chen, Y.-T., Dou, J.-M., Li, D.-C., Wang, D.-Q. & Zhu, Y.-H. (2007). Acta Cryst. E63, m2503–m2504. Web of Science CSD CrossRef IUCr Journals Google Scholar
Dou, J. M., Liu, M. L., Li, D. C. & Wang, D. Q. (2006). Eur. J. Inorg. Chem. 23, 4866–4871. Web of Science CSD CrossRef Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
John, R. P., Park, J., Moon, D., Lee, K. & Lah, M. S. (2006). Chem. Commun. pp. 3699–3701. Web of Science CSD CrossRef Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar

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Volume 64| Part 11| November 2008| Page m1466

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

Bis[2-hydr­­oxy-N′-(2-hy­droxy­benzo­yl)benzohydrazitato]di­pyridine­cadmium(II)

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Bis[2-hydroxy-N′-(2-hydroxybenzoyl)benzohydrazitato]dipyridinecadmium(II)