N,N-Bis(pyridin-2-yl-methyl-idene)pyridine-2,6-dicarbohydrazide dimethyl-formamide monosolvate.

In the crystal of the title compound, C(22)H(22)N(8)O(3), the dicarbohydrazide mol-ecules are linked into a chain along [010] by C-H⋯N inter-actions involving the pyridyl N atoms and aromatic C-H groups. The DMF mol-ecule is hydrogen bonded with the amide N-H via N-H⋯O inter-actions. C-H⋯O inter-actions also occur.

Related literature

For the biological properties of Schiff base ligands, see: Bedia et al. (2006 ▶). For related structures, see: Alhadi et al. (2008 ▶); Nie (2008 ▶).

Experimental

Crystal data

C22H22N8O3

M = 446.48

Monoclinic,

a = 10.0944 (9) Å

b = 24.639 (2) Å

c = 9.6552 (8) Å

β = 110.826 (2)°

V = 2244.5 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.36 × 0.31 × 0.17 mm

Data collection

Siemens SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.967, T max = 0.984

11220 measured reflections

3945 independent reflections

2291 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.126

S = 1.03

3945 reflections

300 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.17 e Å−3

Data collection: SMART (Siemens, 2007 ▶); cell refinement: SAINT (Siemens, 2007 ▶); 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810039346/ds2055sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810039346/ds2055Isup2.hkl

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

C19H15N7O2·C3H7NO	F(000) = 936
Mr = 446.48	Dx = 1.321 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2269 reflections
a = 10.0944 (9) Å	θ = 2.3–22.5°
b = 24.639 (2) Å	µ = 0.09 mm−1
c = 9.6552 (8) Å	T = 298 K
β = 110.826 (2)°	Block, red
V = 2244.5 (3) Å3	0.36 × 0.31 × 0.17 mm
Z = 4

Siemens SMART CCD area-detector diffractometer	3945 independent reflections
Radiation source: fine-focus sealed tube	2291 reflections with I > 2σ(I)
graphite	Rint = 0.040
phi and ω scans	θmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→12
Tmin = 0.967, Tmax = 0.984	k = −25→29
11220 measured reflections	l = −11→9

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) = 0.126	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0422P)2 + 0.8005P] where P = (Fo2 + 2Fc2)/3
3945 reflections	(Δ/σ)max < 0.001
300 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.17 e Å−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
N1	1.0532 (2)	0.06010 (8)	0.6046 (2)	0.0399 (5)
N2	0.8597 (2)	0.13178 (8)	0.4467 (2)	0.0478 (6)
H2	0.8437	0.1064	0.5000	0.057*
N3	0.7529 (2)	0.16653 (8)	0.3698 (2)	0.0468 (6)
N4	0.3891 (2)	0.17800 (9)	0.3134 (3)	0.0544 (6)
N5	0.9686 (2)	−0.00721 (8)	0.7745 (2)	0.0453 (5)
H5	0.9187	0.0193	0.7246	0.054*
N6	0.9148 (2)	−0.04071 (8)	0.8553 (2)	0.0446 (5)
N7	0.5832 (2)	−0.05299 (9)	0.8981 (3)	0.0593 (7)
N8	0.8324 (2)	0.16209 (9)	0.8702 (2)	0.0538 (6)
O1	1.02185 (19)	0.17371 (7)	0.3714 (2)	0.0590 (5)
O2	1.1763 (2)	−0.05273 (8)	0.8419 (2)	0.0643 (6)
O3	0.7810 (2)	0.09334 (7)	0.7038 (2)	0.0647 (6)
C1	0.9891 (3)	0.13729 (10)	0.4390 (3)	0.0435 (6)
C2	1.0946 (3)	0.09502 (9)	0.5217 (3)	0.0397 (6)
C3	1.2263 (3)	0.09326 (10)	0.5094 (3)	0.0483 (7)
H3	1.2512	0.1182	0.4506	0.058*
C4	1.3202 (3)	0.05384 (11)	0.5861 (3)	0.0564 (8)
H4	1.4097	0.0516	0.5794	0.068*
C5	1.2802 (3)	0.01771 (11)	0.6728 (3)	0.0524 (7)
H5A	1.3422	−0.0092	0.7256	0.063*
C6	1.1465 (3)	0.02221 (9)	0.6800 (3)	0.0405 (6)
C7	1.1003 (3)	−0.01612 (10)	0.7739 (3)	0.0431 (6)
C8	0.6315 (3)	0.15664 (10)	0.3761 (3)	0.0489 (7)
H8	0.6194	0.1272	0.4308	0.059*
C9	0.5108 (3)	0.19145 (10)	0.2974 (3)	0.0454 (7)
C10	0.5215 (3)	0.23516 (11)	0.2119 (3)	0.0607 (8)
H10	0.6081	0.2438	0.2036	0.073*
C11	0.4044 (4)	0.26539 (12)	0.1401 (3)	0.0659 (9)
H11	0.4100	0.2950	0.0828	0.079*
C12	0.2779 (3)	0.25150 (12)	0.1535 (3)	0.0621 (8)
H12	0.1958	0.2711	0.1044	0.075*
C13	0.2757 (3)	0.20829 (12)	0.2407 (3)	0.0614 (8)
H13	0.1899	0.1993	0.2502	0.074*
C14	0.7866 (3)	−0.03185 (10)	0.8425 (3)	0.0466 (7)
H14	0.7361	−0.0040	0.7815	0.056*
C15	0.7184 (3)	−0.06509 (10)	0.9230 (3)	0.0429 (6)
C16	0.7895 (3)	−0.10600 (10)	1.0182 (3)	0.0495 (7)
H16	0.8846	−0.1128	1.0347	0.059*
C17	0.7184 (3)	−0.13655 (11)	1.0882 (3)	0.0573 (8)
H17	0.7637	−0.1647	1.1513	0.069*
C18	0.5798 (3)	−0.12467 (12)	1.0632 (3)	0.0619 (8)
H18	0.5286	−0.1446	1.1089	0.074*
C19	0.5177 (3)	−0.08291 (13)	0.9697 (4)	0.0680 (9)
H19	0.4237	−0.0748	0.9550	0.082*
C20	0.7886 (3)	0.11313 (12)	0.8238 (3)	0.0567 (8)
H20	0.7607	0.0912	0.8870	0.068*
C21	0.8856 (4)	0.19753 (12)	0.7832 (4)	0.0753 (10)
H21A	0.9833	0.1892	0.8016	0.113*
H21B	0.8776	0.2346	0.8101	0.113*
H21C	0.8314	0.1924	0.6799	0.113*
C22	0.8389 (4)	0.18074 (14)	1.0149 (4)	0.0905 (12)
H22A	0.8091	0.1521	1.0646	0.136*
H22B	0.7774	0.2115	1.0035	0.136*
H22C	0.9344	0.1910	1.0724	0.136*

	U11	U22	U33	U12	U13	U23
N1	0.0422 (12)	0.0380 (11)	0.0372 (12)	−0.0013 (10)	0.0111 (10)	−0.0001 (10)
N2	0.0479 (14)	0.0483 (13)	0.0485 (14)	0.0057 (11)	0.0187 (12)	0.0119 (11)
N3	0.0480 (14)	0.0495 (13)	0.0416 (14)	0.0077 (11)	0.0145 (11)	0.0060 (11)
N4	0.0495 (14)	0.0638 (15)	0.0505 (15)	0.0082 (12)	0.0186 (12)	0.0115 (12)
N5	0.0477 (13)	0.0416 (12)	0.0483 (14)	0.0007 (10)	0.0192 (11)	0.0087 (10)
N6	0.0494 (14)	0.0399 (12)	0.0470 (14)	−0.0032 (10)	0.0203 (12)	0.0024 (10)
N7	0.0485 (15)	0.0632 (15)	0.0695 (18)	0.0088 (12)	0.0250 (13)	0.0170 (13)
N8	0.0674 (16)	0.0472 (14)	0.0459 (15)	0.0036 (12)	0.0189 (13)	0.0027 (12)
O1	0.0569 (12)	0.0580 (12)	0.0641 (14)	0.0013 (9)	0.0240 (11)	0.0191 (10)
O2	0.0577 (13)	0.0570 (12)	0.0801 (16)	0.0126 (10)	0.0268 (12)	0.0261 (11)
O3	0.0962 (16)	0.0493 (11)	0.0570 (14)	0.0045 (11)	0.0377 (13)	0.0016 (10)
C1	0.0471 (16)	0.0466 (16)	0.0365 (16)	−0.0029 (13)	0.0144 (13)	0.0008 (13)
C2	0.0436 (15)	0.0393 (14)	0.0345 (15)	−0.0028 (12)	0.0118 (12)	−0.0021 (12)
C3	0.0510 (17)	0.0504 (16)	0.0463 (17)	−0.0022 (13)	0.0207 (14)	0.0058 (13)
C4	0.0468 (17)	0.0632 (18)	0.064 (2)	0.0018 (15)	0.0250 (16)	0.0072 (16)
C5	0.0450 (16)	0.0546 (17)	0.0570 (19)	0.0076 (13)	0.0173 (15)	0.0065 (15)
C6	0.0443 (15)	0.0358 (14)	0.0386 (16)	−0.0006 (12)	0.0113 (13)	−0.0014 (12)
C7	0.0447 (16)	0.0377 (14)	0.0448 (17)	0.0009 (12)	0.0134 (14)	0.0009 (12)
C8	0.0548 (18)	0.0493 (16)	0.0440 (17)	0.0065 (14)	0.0194 (14)	0.0116 (13)
C9	0.0484 (16)	0.0496 (16)	0.0381 (16)	0.0049 (13)	0.0152 (14)	0.0029 (13)
C10	0.063 (2)	0.0606 (19)	0.062 (2)	0.0068 (16)	0.0265 (17)	0.0139 (16)
C11	0.081 (2)	0.0568 (19)	0.057 (2)	0.0143 (17)	0.0205 (18)	0.0143 (15)
C12	0.061 (2)	0.067 (2)	0.051 (2)	0.0235 (17)	0.0111 (16)	0.0045 (16)
C13	0.0514 (18)	0.075 (2)	0.058 (2)	0.0107 (16)	0.0188 (16)	0.0044 (17)
C14	0.0503 (17)	0.0375 (14)	0.0518 (18)	0.0025 (13)	0.0179 (14)	0.0038 (13)
C15	0.0437 (16)	0.0384 (14)	0.0444 (16)	−0.0019 (12)	0.0128 (13)	−0.0015 (12)
C16	0.0457 (16)	0.0472 (16)	0.0559 (18)	0.0020 (13)	0.0183 (14)	0.0030 (14)
C17	0.061 (2)	0.0515 (17)	0.057 (2)	0.0003 (15)	0.0191 (16)	0.0122 (15)
C18	0.059 (2)	0.0658 (19)	0.065 (2)	−0.0070 (16)	0.0279 (17)	0.0115 (17)
C19	0.0472 (18)	0.082 (2)	0.078 (2)	0.0073 (16)	0.0266 (17)	0.0209 (19)
C20	0.072 (2)	0.0517 (18)	0.053 (2)	0.0035 (15)	0.0305 (17)	0.0106 (15)
C21	0.094 (3)	0.0557 (19)	0.086 (3)	−0.0023 (17)	0.044 (2)	0.0063 (18)
C22	0.132 (3)	0.083 (2)	0.053 (2)	−0.004 (2)	0.030 (2)	−0.0114 (18)

N1—C2	1.339 (3)	C6—C7	1.494 (3)
N1—C6	1.342 (3)	C8—C9	1.463 (3)
N2—C1	1.342 (3)	C8—H8	0.9300
N2—N3	1.370 (3)	C9—C10	1.384 (3)
N2—H2	0.8600	C10—C11	1.360 (4)
N3—C8	1.272 (3)	C10—H10	0.9300
N4—C9	1.333 (3)	C11—C12	1.372 (4)
N4—C13	1.338 (3)	C11—H11	0.9300
N5—C7	1.349 (3)	C12—C13	1.362 (4)
N5—N6	1.373 (3)	C12—H12	0.9300
N5—H5	0.8600	C13—H13	0.9300
N6—C14	1.275 (3)	C14—C15	1.459 (3)
N7—C15	1.332 (3)	C14—H14	0.9300
N7—C19	1.336 (3)	C15—C16	1.381 (3)
N8—C20	1.308 (3)	C16—C17	1.373 (3)
N8—C21	1.441 (3)	C16—H16	0.9300
N8—C22	1.450 (4)	C17—C18	1.364 (4)
O1—C1	1.222 (3)	C17—H17	0.9300
O2—C7	1.215 (3)	C18—C19	1.365 (4)
O3—C20	1.234 (3)	C18—H18	0.9300
C1—C2	1.500 (3)	C19—H19	0.9300
C2—C3	1.377 (3)	C20—H20	0.9300
C3—C4	1.375 (3)	C21—H21A	0.9600
C3—H3	0.9300	C21—H21B	0.9600
C4—C5	1.378 (4)	C21—H21C	0.9600
C4—H4	0.9300	C22—H22A	0.9600
C5—C6	1.380 (3)	C22—H22B	0.9600
C5—H5A	0.9300	C22—H22C	0.9600
C2—N1—C6	117.6 (2)	C9—C10—H10	120.3
C1—N2—N3	120.0 (2)	C10—C11—C12	119.0 (3)
C1—N2—H2	120.0	C10—C11—H11	120.5
N3—N2—H2	120.0	C12—C11—H11	120.5
C8—N3—N2	116.1 (2)	C13—C12—C11	118.3 (3)
C9—N4—C13	116.9 (2)	C13—C12—H12	120.9
C7—N5—N6	119.6 (2)	C11—C12—H12	120.9
C7—N5—H5	120.2	N4—C13—C12	124.2 (3)
N6—N5—H5	120.2	N4—C13—H13	117.9
C14—N6—N5	115.8 (2)	C12—C13—H13	117.9
C15—N7—C19	116.5 (2)	N6—C14—C15	120.5 (2)
C20—N8—C21	120.6 (2)	N6—C14—H14	119.8
C20—N8—C22	121.1 (3)	C15—C14—H14	119.8
C21—N8—C22	118.1 (3)	N7—C15—C16	122.7 (2)
O1—C1—N2	123.9 (2)	N7—C15—C14	115.1 (2)
O1—C1—C2	121.2 (2)	C16—C15—C14	122.2 (2)
N2—C1—C2	114.9 (2)	C17—C16—C15	119.2 (2)
N1—C2—C3	123.1 (2)	C17—C16—H16	120.4
N1—C2—C1	116.8 (2)	C15—C16—H16	120.4
C3—C2—C1	120.0 (2)	C18—C17—C16	118.6 (3)
C4—C3—C2	118.6 (2)	C18—C17—H17	120.7
C4—C3—H3	120.7	C16—C17—H17	120.7
C2—C3—H3	120.7	C17—C18—C19	118.7 (3)
C3—C4—C5	119.2 (2)	C17—C18—H18	120.7
C3—C4—H4	120.4	C19—C18—H18	120.7
C5—C4—H4	120.4	N7—C19—C18	124.3 (3)
C4—C5—C6	118.8 (3)	N7—C19—H19	117.9
C4—C5—H5A	120.6	C18—C19—H19	117.9
C6—C5—H5A	120.6	O3—C20—N8	125.9 (3)
N1—C6—C5	122.6 (2)	O3—C20—H20	117.0
N1—C6—C7	117.3 (2)	N8—C20—H20	117.0
C5—C6—C7	120.1 (2)	N8—C21—H21A	109.5
O2—C7—N5	123.5 (2)	N8—C21—H21B	109.5
O2—C7—C6	121.6 (2)	H21A—C21—H21B	109.5
N5—C7—C6	114.9 (2)	N8—C21—H21C	109.5
N3—C8—C9	120.1 (2)	H21A—C21—H21C	109.5
N3—C8—H8	119.9	H21B—C21—H21C	109.5
C9—C8—H8	119.9	N8—C22—H22A	109.5
N4—C9—C10	122.2 (2)	N8—C22—H22B	109.5
N4—C9—C8	115.2 (2)	H22A—C22—H22B	109.5
C10—C9—C8	122.6 (2)	N8—C22—H22C	109.5
C11—C10—C9	119.5 (3)	H22A—C22—H22C	109.5
C11—C10—H10	120.3	H22B—C22—H22C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O3	0.86	2.29	3.015 (3)	142
N5—H5···O3	0.86	2.26	3.045 (3)	152
N2—H2···O3	0.86	2.29	3.015 (3)	142
N5—H5···O3	0.86	2.26	3.045 (3)	152
C22—H22A···O2i	0.96	2.59	3.469 (4)	152
C12—H12···O1ii	0.93	2.68	3.534 (3)	153
C11—H11···N4iii	0.93	2.62	3.402 (4)	142
C3—H3···N4iv	0.93	2.68	3.585 (3)	165
C5—H5A···N7iv	0.93	2.64	3.520 (4)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O3	0.86	2.29	3.015 (3)	142
N5—H5⋯O3	0.86	2.26	3.045 (3)	152
N2—H2⋯O3	0.86	2.29	3.015 (3)	142
N5—H5⋯O3	0.86	2.26	3.045 (3)	152
C22—H22A⋯O2i	0.96	2.59	3.469 (4)	152
C12—H12⋯O1ii	0.93	2.68	3.534 (3)	153
C11—H11⋯N4iii	0.93	2.62	3.402 (4)	142
C3—H3⋯N4iv	0.93	2.68	3.585 (3)	165
C5—H5A⋯N7iv	0.93	2.64	3.520 (4)	158

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .