2,2′-[Pyridine-2,6-diylbis(carbonyl­hydrazono)]dipropanoic acid N,N-dimethyl­formamide disolvate

Qiao, Y.; Cui, J.; Ding, L.; Yin, H.

doi:10.1107/S160053680903997X

organic compounds

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2,2′-[Pyridine-2,6-diylbis(carbonylhydrazono)]dipropanoic acid N,N-dimethylformamide disolvate

Yanling Qiao,^a Jichun Cui,^a Longhua Ding ^a and Handong Yin ^a ^*

^aCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China
^*Correspondence e-mail: handongyin@163.com

(Received 21 September 2009; accepted 1 October 2009; online 7 October 2009)

The complete molecule of the title compound, C₁₃H₁₃N₅O₆·2C₃H₇NO, is generated by crystallographic twofold rotation with an N and a C atom lying on the axis. The structure is stabilized by intermolecular O—H⋯O hydrogen bonds.

Related literature

For the synthesis and structures of some organotin(IV) complexes of related tridentate hydrazone ligands see: Yin et al. (2008 ).

Experimental

Crystal data

C₁₃H₁₃N₅O₆·2C₃H₇NO
M_r = 481.48
Monoclinic, C 2/c
a = 19.5743 (17) Å
b = 10.4041 (11) Å
c = 11.7924 (12) Å
β = 107.684 (1)°
V = 2288.1 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 298 K
0.40 × 0.39 × 0.17 mm

Data collection

Siemens CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.957, T_max = 0.981
5528 measured reflections
2017 independent reflections
1102 reflections with I > 2σ(I)
R_int = 0.041

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.137
S = 1.00
2017 reflections
158 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O4	0.82	1.75	2.574 (3)	178

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: https://doi.org/10.1107/S160053680903997X/sj2660sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053680903997X/sj2660Isup2.hkl

checkCIF report

Comment top

Recently, we have reported some organotin(IV) complexes with hydrazone ligands (Yin et al., 2008). As an extension of our work on the structural characterization of hydrazone compounds, the title compound, (I), is reported here.

The two halves of the main molecule are symmetrically related, Fig. 1, with the N1, C4 and H4 atoms of the pyridine ring lying on the two-fold axis to form a helical species. The N3═C6 bond length of 1.283 (3) Å (Table 1) conforms to the value for a double bond, while the N2—C1 [1.361 (3) Å] and N2—N3 [1.369 (3) Å] bonds are intermediate between a double bond and a single bond because of conjugation effects in the molecule.

Related literature top

For the synthesis and structures of some organotin(IV) complexes of related tridentate hydrazone ligands see: Yin et al. (2008).

Experimental top

Compound (I) was synthesized by the reaction of pyridine-2,6-dihydrazide (5 mmol) with pyruvic acid (10 mmol). Single crystals of (I) suitable for X-ray diffraction were obtained by slow evaporation of an N,N-dimethylformamide solution.

Structure description top

For the synthesis and structures of some organotin(IV) complexes of related tridentate hydrazone ligands see: Yin et al. (2008).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (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 structure of the title compound, with 50% probability displacement ellipsoids and hydrogen bonds drawn as dashed lines. H atoms not involved in hydrogen bonding have been omitted for clarity.

2,2'-[Pyridine-2,6-diylbis(carbonylhydrazono)]dipropanoic acid N,N-dimethylformamide disolvate top

Crystal data top

C₁₃H₁₃N₅O₆·2C₃H₇NO	F(000) = 1016
M_r = 481.48	D_x = 1.398 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1027 reflections
a = 19.5743 (17) Å	θ = 2.2–21.9°
b = 10.4041 (11) Å	µ = 0.11 mm⁻¹
c = 11.7924 (12) Å	T = 298 K
β = 107.684 (1)°	Block, colorless
V = 2288.1 (4) Å³	0.40 × 0.39 × 0.17 mm
Z = 4

Data collection top

Siemens CCD area-detector diffractometer	2017 independent reflections
Radiation source: fine-focus sealed tube	1102 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
φ and ω scans	θ_max = 25.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −23→23
T_min = 0.957, T_max = 0.981	k = −6→12
5528 measured reflections	l = −12→14

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.137	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0581P)² + 0.8585P] where P = (F_o² + 2F_c²)/3
2017 reflections	(Δ/σ)_max = 0.004
158 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.14 e Å⁻³

Crystal data top

C₁₃H₁₃N₅O₆·2C₃H₇NO	V = 2288.1 (4) Å³
M_r = 481.48	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 19.5743 (17) Å	µ = 0.11 mm⁻¹
b = 10.4041 (11) Å	T = 298 K
c = 11.7924 (12) Å	0.40 × 0.39 × 0.17 mm
β = 107.684 (1)°

Data collection top

Siemens CCD area-detector diffractometer	2017 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1102 reflections with I > 2σ(I)
T_min = 0.957, T_max = 0.981	R_int = 0.041
5528 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.137	H-atom parameters constrained
S = 1.00	Δρ_max = 0.20 e Å⁻³
2017 reflections	Δρ_min = −0.14 e Å⁻³
158 parameters

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

	x	y	z	U_iso*/U_eq
N1	0.5000	0.2225 (3)	0.7500	0.0370 (8)
N2	0.56173 (12)	0.3597 (2)	0.6173 (2)	0.0440 (6)
H2	0.5454	0.3894	0.6721	0.053*
N3	0.58981 (11)	0.4428 (2)	0.55325 (18)	0.0414 (6)
N4	0.71491 (12)	1.0005 (2)	0.3217 (2)	0.0492 (7)
O1	0.58033 (11)	0.18075 (19)	0.52026 (18)	0.0608 (6)
O2	0.62171 (12)	0.76940 (19)	0.54017 (18)	0.0615 (6)
O3	0.64206 (11)	0.60873 (17)	0.43031 (16)	0.0539 (6)
H3	0.6570	0.6669	0.3972	0.081*
O4	0.69084 (11)	0.78824 (19)	0.32604 (17)	0.0546 (6)
C1	0.55919 (15)	0.2310 (3)	0.5960 (2)	0.0414 (7)
C2	0.52726 (14)	0.1563 (2)	0.6765 (2)	0.0365 (7)
C3	0.52768 (15)	0.0235 (3)	0.6730 (2)	0.0472 (7)
H3A	0.5462	−0.0199	0.6199	0.057*
C4	0.5000	−0.0427 (4)	0.7500	0.0550 (12)
H4	0.5000	−0.1320	0.7500	0.066*
C5	0.62039 (14)	0.6566 (3)	0.5162 (2)	0.0417 (7)
C6	0.59176 (14)	0.5610 (3)	0.5853 (2)	0.0394 (7)
C7	0.56634 (16)	0.6134 (3)	0.6825 (3)	0.0569 (9)
H7A	0.5151	0.6058	0.6610	0.085*
H7B	0.5797	0.7023	0.6950	0.085*
H7C	0.5878	0.5660	0.7544	0.085*
C8	0.69523 (15)	0.8983 (3)	0.3682 (3)	0.0502 (8)
H8	0.6836	0.9088	0.4385	0.060*
C9	0.73224 (17)	0.9912 (3)	0.2111 (3)	0.0645 (10)
H9A	0.7245	0.9046	0.1818	0.097*
H9B	0.7816	1.0141	0.2246	0.097*
H9C	0.7021	1.0486	0.1536	0.097*
C10	0.7204 (2)	1.1255 (3)	0.3783 (3)	0.0787 (11)
H10A	0.6987	1.1220	0.4412	0.118*
H10B	0.6961	1.1884	0.3206	0.118*
H10C	0.7700	1.1488	0.4106	0.118*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0357 (18)	0.0301 (17)	0.0426 (18)	0.000	0.0078 (15)	0.000
N2	0.0566 (16)	0.0331 (13)	0.0493 (14)	−0.0003 (12)	0.0264 (12)	0.0034 (11)
N3	0.0420 (14)	0.0390 (14)	0.0456 (14)	0.0005 (12)	0.0170 (11)	0.0080 (12)
N4	0.0583 (16)	0.0443 (14)	0.0490 (15)	−0.0039 (13)	0.0222 (13)	0.0069 (13)
O1	0.0845 (16)	0.0466 (13)	0.0638 (14)	−0.0028 (12)	0.0410 (12)	−0.0082 (11)
O2	0.0899 (17)	0.0351 (12)	0.0710 (15)	−0.0122 (12)	0.0419 (13)	−0.0040 (11)
O3	0.0756 (14)	0.0412 (12)	0.0559 (13)	−0.0021 (11)	0.0360 (11)	0.0046 (10)
O4	0.0693 (14)	0.0457 (13)	0.0542 (13)	−0.0067 (11)	0.0268 (11)	0.0046 (11)
C1	0.0444 (17)	0.0342 (16)	0.0452 (17)	0.0023 (14)	0.0129 (14)	−0.0011 (14)
C2	0.0395 (16)	0.0276 (15)	0.0402 (16)	0.0001 (13)	0.0089 (13)	−0.0028 (13)
C3	0.0542 (19)	0.0338 (16)	0.0558 (19)	0.0004 (15)	0.0202 (15)	−0.0081 (15)
C4	0.075 (3)	0.025 (2)	0.073 (3)	0.000	0.034 (3)	0.000
C5	0.0407 (17)	0.0444 (19)	0.0420 (17)	−0.0004 (15)	0.0154 (14)	0.0015 (14)
C6	0.0404 (17)	0.0343 (16)	0.0459 (16)	0.0010 (14)	0.0169 (13)	0.0038 (14)
C7	0.075 (2)	0.0429 (18)	0.065 (2)	−0.0003 (17)	0.0401 (18)	−0.0006 (16)
C8	0.055 (2)	0.054 (2)	0.0442 (17)	−0.0059 (17)	0.0193 (15)	0.0034 (16)
C9	0.081 (2)	0.062 (2)	0.057 (2)	−0.0082 (19)	0.0322 (18)	0.0150 (17)
C10	0.108 (3)	0.048 (2)	0.093 (3)	−0.009 (2)	0.049 (2)	−0.008 (2)

Geometric parameters (Å, º) top

N1—C2ⁱ	1.339 (3)	C3—C4	1.375 (3)
N1—C2	1.339 (3)	C3—H3A	0.9300
N2—C1	1.361 (3)	C4—C3ⁱ	1.375 (3)
N2—N3	1.369 (3)	C4—H4	0.9300
N2—H2	0.8600	C5—C6	1.499 (4)
N3—C6	1.283 (3)	C6—C7	1.485 (4)
N4—C8	1.308 (3)	C7—H7A	0.9600
N4—C9	1.447 (3)	C7—H7B	0.9600
N4—C10	1.451 (4)	C7—H7C	0.9600
O1—C1	1.211 (3)	C8—H8	0.9300
O2—C5	1.205 (3)	C9—H9A	0.9600
O3—C5	1.310 (3)	C9—H9B	0.9600
O3—H3	0.8200	C9—H9C	0.9600
O4—C8	1.241 (3)	C10—H10A	0.9600
C1—C2	1.503 (4)	C10—H10B	0.9600
C2—C3	1.382 (4)	C10—H10C	0.9600

C2ⁱ—N1—C2	118.0 (3)	N3—C6—C7	126.3 (2)
C1—N2—N3	121.2 (2)	N3—C6—C5	117.3 (2)
C1—N2—H2	119.4	C7—C6—C5	116.4 (2)
N3—N2—H2	119.4	C6—C7—H7A	109.5
C6—N3—N2	115.1 (2)	C6—C7—H7B	109.5
C8—N4—C9	120.2 (3)	H7A—C7—H7B	109.5
C8—N4—C10	121.7 (3)	C6—C7—H7C	109.5
C9—N4—C10	118.0 (3)	H7A—C7—H7C	109.5
C5—O3—H3	109.5	H7B—C7—H7C	109.5
O1—C1—N2	124.0 (3)	O4—C8—N4	125.1 (3)
O1—C1—C2	123.0 (2)	O4—C8—H8	117.4
N2—C1—C2	113.0 (2)	N4—C8—H8	117.4
N1—C2—C3	122.8 (3)	N4—C9—H9A	109.5
N1—C2—C1	117.8 (2)	N4—C9—H9B	109.5
C3—C2—C1	119.4 (2)	H9A—C9—H9B	109.5
C4—C3—C2	118.3 (3)	N4—C9—H9C	109.5
C4—C3—H3A	120.9	H9A—C9—H9C	109.5
C2—C3—H3A	120.9	H9B—C9—H9C	109.5
C3—C4—C3ⁱ	119.9 (4)	N4—C10—H10A	109.5
C3—C4—H4	120.1	N4—C10—H10B	109.5
C3ⁱ—C4—H4	120.1	H10A—C10—H10B	109.5
O2—C5—O3	124.2 (3)	N4—C10—H10C	109.5
O2—C5—C6	120.3 (3)	H10A—C10—H10C	109.5
O3—C5—C6	115.5 (2)	H10B—C10—H10C	109.5

Symmetry code: (i) −x+1, y, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O4	0.82	1.75	2.574 (3)	178

Experimental details

Crystal data
Chemical formula	C₁₃H₁₃N₅O₆·2C₃H₇NO
M_r	481.48
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	298
a, b, c (Å)	19.5743 (17), 10.4041 (11), 11.7924 (12)
β (°)	107.684 (1)
V (Å³)	2288.1 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.40 × 0.39 × 0.17

Data collection
Diffractometer	Siemens CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.957, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections	5528, 2017, 1102
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.137, 1.00
No. of reflections	2017
No. of parameters	158
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.14

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O4	0.82	1.75	2.574 (3)	178.4

Acknowledgements

We acknowledge the National Natural Foundation of China (20771053), the Scientific Research Fund of Liaocheng University (X081006) and the Students Science and Technology Innovation Fund of Liaocheng University (SRT08031HX2).

References

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
Yin, H., Cui, J. & Qiao, Y. (2008). Polyhedron, 27, 2157–2166. Web of Science CSD CrossRef CAS Google Scholar

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CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 11| November 2009| Page o2652

https://doi.org/10.1107/S160053680903997X

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

2,2′-[Pyridine-2,6-diylbis(carbonyl­hydrazono)]di­propanoic acid N,N-di­methyl­formamide disolvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2,2′-[Pyridine-2,6-diylbis(carbonylhydrazono)]dipropanoic acid N,N-dimethylformamide disolvate