N2,N2′-Bis(pyridin-2-yl­methyl­idene)pyridine-2,6-dicarbohydrazide dimethyl­formamide monosolvate

Fan, C.-G.; Song, M.

doi:10.1107/S1600536810039346

organic compounds

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ISSN: 2056-9890

Volume 66| Part 11| November 2010| Page o2766

https://doi.org/10.1107/S1600536810039346

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N²,N^2′-Bis(pyridin-2-ylmethylidene)pyridine-2,6-dicarbohydrazide dimethylformamide monosolvate

Chuan-Gang Fan ^a ^* and Ming-zhi Song ^a

^aCollege of Chemistry and Chemical Technology, Binzhou University, Binzhou 256600, Shandong, People's Republic of China
^*Correspondence e-mail: fanchuangang2009@163.com

(Received 7 September 2010; accepted 1 October 2010; online 9 October 2010)

In the crystal of the title compound, C₂₂H₂₂N₈O₃, the dicarbohydrazide molecules are linked into a chain along [010] by C—H⋯N interactions involving the pyridyl N atoms and aromatic C—H groups. The DMF molecule is hydrogen bonded with the amide N—H via N—H⋯O interactions. C—H⋯O interactions 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_r = 446.48
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.045
wR(F²) = 0.126
S = 1.03
3945 reflections
300 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.17 e Å⁻³

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⋯N4^iv	0.93	2.68	3.585 (3)	165
C5—H5A⋯N7^iv	0.93	2.64	3.520 (4)	158
Symmetry codes: (i) -x+2, -y, -z+2; (ii) $[x-1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iv) x+1, y, z.

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.

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810039346/ds2055Isup2.hkl

checkCIF report

Comment top

Schiff bases containing pyridine ring have received considerable attention during the last decades, mainly because their steric and electronic properties can be easily adapted by choosing the right amine and aldehyde precursors(Bedia et al., 2006).

We report here the crystal structure of the title new Schiff base compound (I).

In (I) (Fig. 1), the bond lengths and angles are normal and are comparable to the values observed in similar compounds (Nie et al., 2008; Alhadi et al., 2008). Meanwhile, the structure unit of (I), contains one N'²,N'⁶-bis(pyridin-2-ylmethylene)pyridine-2,6-dicarbohydrazide molecule and one N,N-dimethylformamide solvate molecule. In molecule N'²,N'⁶-bis (pyridin-2-ylmethylene)pyridine-2,6-dicarbohydrazide, the centre pyridine ring and the pyridine rings (n4/c9/c10/c11/c12/c13),(n1/c2/c3/c4/c5/c6) form the dihedral angles of 9.13 (15)°, 4.35 (17)°, respectively, which mean the atoms of the molecule N'²,N'⁶-bis (pyridin-2-ylmethylene)pyridine-2,6-dicarbohydrazide are almost coplanar.

Moreover, the crystal surpermolecular structure was built from the connections of weak intermolecular N—H···O, C—H···O and C—H···N as shown in table 1.

Related literature top

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

Experimental top

Pyridine-2,6-dicarbohydrazide (6 mmol) in DMF (20 ml) was added to pyridine-2-aldehyde (12 mmol). The mixture was refluxed with stirring for 6 h. A red precipitate was then obtained. Red crystals suitable for X-ray diffraction analysis formed after one week on slow evaporation of DMF solution at room temperature. Elemental analysis: calculated for C₂₂H₂₂N₈O₃: C 59.18, H 4.97, N 25.10%; found: C 59.28, H 4.82, N 25.21%.

Structure description top

We report here the crystal structure of the title new Schiff base compound (I).

Moreover, the crystal surpermolecular structure was built from the connections of weak intermolecular N—H···O, C—H···O and C—H···N as shown in table 1.

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

Computing details top

Data collection: SMART (Siemens, 2007); cell refinement: SAINT (Siemens, 2007); data reduction: SAINT (Siemens, 2007); 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 content of asymmetric unit of the title compound showing the atomic numbering scheme and 30% probability displacement ellipsoids.
	Fig. 2. The crystal packing of (I), viewed along the a axis.

N²,N^2'-Bis(pyridin-2-ylmethylidene)pyridine-2,6- dicarbohydrazide dimethylformamide monosolvate top

Crystal data top

C₁₉H₁₅N₇O₂·C₃H₇NO	F(000) = 936
M_r = 446.48	D_x = 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

Data collection top

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

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) = 0.126	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0422P)² + 0.8005P] where P = (F_o² + 2F_c²)/3
3945 reflections	(Δ/σ)_max < 0.001
300 parameters	Δρ_max = 0.17 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₁₉H₁₅N₇O₂·C₃H₇NO	V = 2244.5 (3) Å³
M_r = 446.48	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.0944 (9) Å	µ = 0.09 mm⁻¹
b = 24.639 (2) Å	T = 298 K
c = 9.6552 (8) Å	0.36 × 0.31 × 0.17 mm
β = 110.826 (2)°

Data collection top

Siemens SMART CCD area-detector diffractometer	3945 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2291 reflections with I > 2σ(I)
T_min = 0.967, T_max = 0.984	R_int = 0.040
11220 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.126	H-atom parameters constrained
S = 1.03	Δρ_max = 0.17 e Å⁻³
3945 reflections	Δρ_min = −0.17 e Å⁻³
300 parameters

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
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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···N4^iv	0.93	2.68	3.585 (3)	165
C5—H5A···N7^iv	0.93	2.64	3.520 (4)	158

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

Experimental details

Crystal data
Chemical formula	C₁₉H₁₅N₇O₂·C₃H₇NO
M_r	446.48
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	10.0944 (9), 24.639 (2), 9.6552 (8)
β (°)	110.826 (2)
V (Å³)	2244.5 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.36 × 0.31 × 0.17

Data collection
Diffractometer	Siemens SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.967, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	11220, 3945, 2291
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.126, 1.03
No. of reflections	3945
No. of parameters	300
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.17

Computer programs: SMART (Siemens, 2007), SAINT (Siemens, 2007), 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
N2—H2···O3	0.86	2.29	3.015 (3)	141.5
N5—H5···O3	0.86	2.26	3.045 (3)	152.0
N2—H2···O3	0.86	2.29	3.015 (3)	141.5
N5—H5···O3	0.86	2.26	3.045 (3)	152.0
C22—H22A···O2ⁱ	0.96	2.59	3.469 (4)	151.5
C12—H12···O1ⁱⁱ	0.93	2.68	3.534 (3)	152.9
C11—H11···N4ⁱⁱⁱ	0.93	2.62	3.402 (4)	142.2
C3—H3···N4^iv	0.93	2.68	3.585 (3)	165.1
C5—H5A···N7^iv	0.93	2.64	3.520 (4)	157.9

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

Acknowledgements

The authors acknowledge the financial support of the Foundation of Binzhou University (Nos. BZXYLG200609, BZXYQNLG2005013).

References

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