Bis[2-hydr-oxy-N'-(2-hydroxy-benzo-yl)benzohydrazitato]dipyridine-cadmium(II).

The title complex, [Cd(C(14)H(11)N(2)O(4))(2)(C(5)H(5)N)(2)], exhibits crystallographic twofold symmetry. The Cd(II) atom is located on the twofold rotation axis and reveals a slightly distorted octa-hedral coordination defined by four atoms (N(2)O(2)) from two symmetry-related chelate ligands and two pyridine N atoms. Intra-molecular O-H⋯O and N-H⋯O hydrogen bonds stabilize the mol-ecular conformation while inter-molecular O-H⋯O hydrogen bonding links mol-ecules into a triad, generating a helix along the threefold screw axis.

Related literature

Three manganese n class="Chemical">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 class="Chemical">N)2]

M = 813.10

Trigonal,

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[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.071

S = 1.00

3146 reflections

241 parameters

H-atom parameters constrained

Δρmax = 0.90 e Å−3

Δρmin = −0.32 e Å−3

Absolute structure: Flack (1983 ▶), 1353 Friedel pairs

Flack parameter: −0.06 (3)

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAIn class="Chemical">NT; 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.

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

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

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

[Cd(C14H11N2O4)2(C5H5N)2]	Dx = 1.523 Mg m−3
Mr = 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

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

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(Fo2) + (0.041P)2 + 0.5675P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
3146 reflections	Δρmax = 0.90 e Å−3
241 parameters	Δρmin = −0.32 e Å−3
0 restraints	Absolute structure: Flack (1983), 1353 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.06 (3)

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) .