N′-(2-Furylmethyl­ene)nicotinohydrazide

Qian, H.; Yin, Z.; Zhang, C.; Yao, Z.

doi:10.1107/S1600536809033698

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 9| September 2009| Page o2260

doi:10.1107/S1600536809033698

Open

access

N′-(2-Furylmethylene)nicotinohydrazide

Heng-yu Qian,^a Zhi-gang Yin,^a ^* Chun-xia Zhang ^a and Zhi-qiang Yao ^a

^aKey Laboratory of Surface and Interface Science of Henan, School of Materials & Chemical Engineering, Zhengzhou University of Light Industry, Zhengzhou 450002, People's Republic of China
^*Correspondence e-mail: yinck@263.net

(Received 19 August 2009; accepted 24 August 2009; online 29 August 2009)

The asymmetric unit of the title compound, C₁₁H₉N₃O₂, contains two independent molecules: the dihedral angles between the pyridine ring and the furyl ring are 17.00 (16) and 34.12 (15)°. The crystal structure involves intermolecular C—H⋯O, N—H⋯N and N—H⋯O hydrogen bonds.

Related literature

For the role played by Schiff bases in the development of various proteins and enzymes, see: Kahwa et al. (1986 ); Santos et al. (2001 ).

Experimental

Crystal data

C₁₁H₉N₃O₂
M_r = 215.21
Monoclinic, C c
a = 17.4363 (3) Å
b = 16.9143 (3) Å
c = 7.9639 (1) Å
β = 115.326 (1)°
V = 2122.99 (6) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 K
0.34 × 0.24 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998 ) T_min = 0.964, T_max = 0.981
9336 measured reflections
2443 independent reflections
1908 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.086
S = 1.06
2443 reflections
290 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.10 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O4ⁱ	0.86	2.26	3.080 (2)	161
N2—H2A⋯N4ⁱ	0.86	2.51	3.112 (3)	128
N5—H5A⋯O2ⁱⁱ	0.86	2.01	2.843 (3)	162
C8—H8A⋯O4ⁱ	0.93	2.56	3.433 (3)	156
C16—H16A⋯O2ⁱⁱ	0.93	2.45	3.228 (3)	141
C22—H22A⋯O2ⁱⁱ	0.93	2.43	3.260 (3)	149
Symmetry codes: (i) $[x-{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ ; (ii) $[x, -y, z-{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); 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 global, I. DOI: 10.1107/S1600536809033698/hg2558sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809033698/hg2558Isup2.hkl

checkCIF report

Comment top

The chemistry of Schiff bases has attracted a great deal of interest in recent years. These compounds play an important role in the development of various proteins and enzymes (Kahwa et al., 1986; Santos et al., 2001). As part of our in the study of the coordination chemistry of Schiff bases, we synthesized the title compound and determined its crystal structure.

The molecular structure is shown in Fig.1. Each molecule is not planar, making the dihedral angle of 17.00 (16) and 34.12 (15)° between pyridine and furyl rings, respectively. In the crystal structure, molecules are linked through intermolecular C—H···O, N—H···N and N—H···O hydrogen bonds, forming a network.

Related literature top

For the role played by Schiff bases in the development of various

proteins and enzymes, see: Kahwa et al. (1986); Santos et al. (2001).

Experimental top

Pyridine-4-carboxylic acid hydrazide (1 mmol, 0.137 g) was dissolved in anhydrous ethanol (15 ml), The mixture was stirred for several minutes at 351 K. Furan-2-carbaldehyde (1 mmol, 0.96 g) in ethanol (8 mm l) was added dropwise and the mixture was stirred at refluxing temperature for 2 h. The product was isolated and recrystallized from methanol. Pink single crystals of (I) was obtained after 3 d.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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 ORTEP plot of (I). Displacement ellipsoids are drawn at the 30% probability level.

N'-(2-Furylmethylene)nicotinohydrazide top

Crystal data top

C₁₁H₉N₃O₂	F(000) = 896
M_r = 215.21	D_x = 1.347 Mg m⁻³
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 2878 reflections
a = 17.4363 (3) Å	θ = 2.4–26.0°
b = 16.9143 (3) Å	µ = 0.10 mm⁻¹
c = 7.9639 (1) Å	T = 296 K
β = 115.326 (1)°	Block, pink
V = 2122.99 (6) Å³	0.34 × 0.24 × 0.15 mm
Z = 8

Data collection top

Bruker SMART CCD area-detector diffractometer	2443 independent reflections
Radiation source: fine-focus sealed tube	1908 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ω scans	θ_max = 27.5°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −22→15
T_min = 0.964, T_max = 0.981	k = −20→21
9336 measured reflections	l = −7→10

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.086	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0488P)²] where P = (F_o² + 2F_c²)/3
2443 reflections	(Δ/σ)_max = 0.006
290 parameters	Δρ_max = 0.10 e Å⁻³
2 restraints	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₁₁H₉N₃O₂	V = 2122.99 (6) Å³
M_r = 215.21	Z = 8
Monoclinic, Cc	Mo Kα radiation
a = 17.4363 (3) Å	µ = 0.10 mm⁻¹
b = 16.9143 (3) Å	T = 296 K
c = 7.9639 (1) Å	0.34 × 0.24 × 0.15 mm
β = 115.326 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2443 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1998)	1908 reflections with I > 2σ(I)
T_min = 0.964, T_max = 0.981	R_int = 0.026
9336 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	2 restraints
wR(F²) = 0.086	H-atom parameters constrained
S = 1.06	Δρ_max = 0.10 e Å⁻³
2443 reflections	Δρ_min = −0.16 e Å⁻³
290 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	0.20002 (12)	0.30973 (11)	0.8151 (3)	0.0512 (4)
N2	0.15397 (11)	0.29763 (11)	0.6278 (2)	0.0500 (4)
H2A	0.1101	0.3262	0.5653	0.060*
O4	0.52299 (10)	−0.06828 (10)	0.4681 (3)	0.0659 (5)
N4	0.45709 (11)	−0.21482 (11)	0.4338 (2)	0.0505 (5)
N5	0.40911 (11)	−0.14890 (11)	0.3504 (3)	0.0522 (5)
H5A	0.3552	−0.1532	0.2855	0.063*
C6	0.17831 (13)	0.24079 (13)	0.5439 (3)	0.0503 (5)
C17	0.44693 (14)	−0.07807 (13)	0.3711 (3)	0.0490 (5)
O1	0.27842 (12)	0.33154 (12)	1.1928 (2)	0.0715 (5)
O2	0.23970 (12)	0.19833 (11)	0.6284 (3)	0.0763 (6)
C7	0.12722 (13)	0.23106 (12)	0.3412 (3)	0.0461 (5)
O3	0.53896 (10)	−0.35845 (9)	0.5715 (2)	0.0622 (4)
C18	0.39031 (13)	−0.01116 (13)	0.2696 (3)	0.0478 (5)
C15	0.45280 (14)	−0.35168 (14)	0.4952 (3)	0.0532 (5)
C5	0.17080 (15)	0.36173 (14)	0.8885 (3)	0.0539 (6)
H5B	0.1217	0.3892	0.8143	0.065*
C16	0.41431 (15)	−0.27691 (14)	0.4225 (3)	0.0553 (6)
H16A	0.3554	−0.2738	0.3644	0.066*
C4	0.21241 (16)	0.37849 (14)	1.0833 (4)	0.0572 (6)
C8	0.07516 (16)	0.28882 (14)	0.2286 (3)	0.0589 (6)
H8A	0.0719	0.3366	0.2829	0.071*
N3	0.02917 (18)	0.28065 (15)	0.0467 (3)	0.0813 (7)
C21	0.28729 (18)	0.10962 (16)	0.0818 (4)	0.0692 (7)
H21A	0.2520	0.1515	0.0195	0.083*
C11	0.13288 (17)	0.16115 (14)	0.2577 (4)	0.0650 (7)
H11A	0.1678	0.1206	0.3283	0.078*
N6	0.26106 (14)	0.03697 (14)	0.0239 (3)	0.0773 (7)
C14	0.41892 (19)	−0.42120 (16)	0.5088 (5)	0.0781 (8)
H14A	0.3614	−0.4324	0.4666	0.094*
C19	0.41546 (17)	0.06558 (14)	0.3224 (4)	0.0628 (6)
H19A	0.4676	0.0759	0.4214	0.075*
C22	0.31279 (16)	−0.02186 (15)	0.1181 (4)	0.0651 (7)
H22A	0.2956	−0.0734	0.0793	0.078*
C3	0.1971 (2)	0.43309 (15)	1.1883 (5)	0.0737 (8)
H3B	0.1554	0.4720	1.1465	0.088*
C9	0.0358 (2)	0.2127 (2)	−0.0274 (4)	0.0796 (8)
H9A	0.0036	0.2059	−0.1543	0.095*
C20	0.36299 (19)	0.12676 (15)	0.2276 (4)	0.0705 (7)
H20A	0.3788	0.1789	0.2621	0.085*
C13	0.4863 (2)	−0.47379 (17)	0.5986 (5)	0.0821 (9)
H13A	0.4821	−0.5263	0.6282	0.098*
C12	0.5564 (2)	−0.43447 (15)	0.6328 (4)	0.0706 (7)
H12A	0.6107	−0.4557	0.6911	0.085*
C1	0.3036 (2)	0.3593 (2)	1.3692 (4)	0.0870 (9)
H1B	0.3482	0.3383	1.4732	0.104*
C10	0.0865 (2)	0.15199 (17)	0.0696 (4)	0.0729 (8)
H10A	0.0897	0.1056	0.0102	0.087*
C2	0.2564 (2)	0.4201 (2)	1.3734 (5)	0.0848 (9)
H2B	0.2614	0.4485	1.4776	0.102*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0387 (9)	0.0551 (10)	0.0519 (11)	0.0008 (8)	0.0119 (9)	0.0000 (8)
N2	0.0347 (9)	0.0544 (10)	0.0500 (10)	0.0077 (8)	0.0078 (8)	0.0012 (8)
O4	0.0354 (8)	0.0574 (9)	0.0832 (12)	−0.0024 (7)	0.0045 (8)	−0.0060 (8)
N4	0.0369 (9)	0.0520 (11)	0.0563 (11)	0.0020 (8)	0.0137 (9)	0.0018 (8)
N5	0.0318 (9)	0.0514 (11)	0.0601 (12)	0.0021 (8)	0.0070 (8)	0.0029 (8)
C6	0.0331 (11)	0.0486 (12)	0.0574 (13)	0.0030 (9)	0.0080 (10)	−0.0008 (10)
C17	0.0360 (11)	0.0504 (12)	0.0527 (12)	−0.0015 (9)	0.0115 (10)	−0.0065 (9)
O1	0.0645 (11)	0.0809 (12)	0.0594 (10)	0.0077 (10)	0.0171 (9)	−0.0046 (9)
O2	0.0533 (10)	0.0745 (11)	0.0689 (11)	0.0264 (9)	−0.0046 (9)	−0.0126 (9)
C7	0.0331 (10)	0.0472 (11)	0.0530 (12)	−0.0021 (9)	0.0138 (10)	0.0000 (9)
O3	0.0452 (9)	0.0555 (9)	0.0781 (11)	0.0037 (8)	0.0189 (9)	0.0055 (8)
C18	0.0370 (11)	0.0504 (12)	0.0522 (12)	−0.0014 (9)	0.0154 (10)	−0.0022 (9)
C15	0.0411 (12)	0.0536 (13)	0.0572 (13)	−0.0022 (10)	0.0138 (11)	0.0001 (10)
C5	0.0457 (12)	0.0527 (12)	0.0616 (15)	0.0026 (10)	0.0214 (12)	0.0041 (10)
C16	0.0355 (11)	0.0578 (14)	0.0616 (14)	−0.0020 (10)	0.0104 (10)	0.0026 (11)
C4	0.0527 (14)	0.0565 (13)	0.0638 (14)	−0.0025 (11)	0.0264 (12)	0.0006 (11)
C8	0.0576 (15)	0.0628 (14)	0.0552 (14)	0.0096 (12)	0.0232 (12)	0.0058 (11)
N3	0.0926 (19)	0.0879 (16)	0.0512 (12)	0.0251 (14)	0.0192 (12)	0.0123 (12)
C21	0.0615 (17)	0.0575 (15)	0.0865 (19)	0.0119 (13)	0.0298 (15)	0.0192 (13)
C11	0.0587 (15)	0.0573 (13)	0.0621 (15)	0.0076 (12)	0.0097 (12)	−0.0028 (11)
N6	0.0512 (13)	0.0676 (14)	0.0881 (16)	0.0060 (11)	0.0060 (12)	0.0147 (12)
C14	0.0587 (16)	0.0559 (15)	0.113 (2)	−0.0062 (13)	0.0302 (17)	0.0049 (14)
C19	0.0551 (14)	0.0523 (14)	0.0685 (15)	−0.0050 (11)	0.0145 (12)	−0.0060 (11)
C22	0.0495 (14)	0.0530 (13)	0.0729 (16)	−0.0022 (11)	0.0073 (13)	0.0017 (12)
C3	0.081 (2)	0.0624 (15)	0.086 (2)	−0.0060 (14)	0.0431 (18)	−0.0135 (14)
C9	0.080 (2)	0.094 (2)	0.0501 (14)	0.0059 (17)	0.0138 (15)	0.0000 (14)
C20	0.0716 (18)	0.0484 (13)	0.0849 (19)	−0.0006 (13)	0.0272 (16)	0.0019 (12)
C13	0.082 (2)	0.0527 (15)	0.110 (3)	0.0018 (15)	0.0400 (19)	0.0111 (15)
C12	0.0660 (17)	0.0595 (15)	0.0796 (17)	0.0141 (13)	0.0246 (14)	0.0079 (13)
C1	0.078 (2)	0.107 (3)	0.0601 (18)	−0.015 (2)	0.0146 (16)	−0.0101 (16)
C10	0.0745 (18)	0.0722 (18)	0.0628 (16)	−0.0057 (15)	0.0206 (14)	−0.0127 (13)
C2	0.103 (2)	0.082 (2)	0.082 (2)	−0.0289 (18)	0.052 (2)	−0.0266 (16)

Geometric parameters (Å, º) top

N1—C5	1.277 (3)	C8—N3	1.329 (3)
N1—N2	1.374 (3)	C8—H8A	0.9300
N2—C6	1.339 (3)	N3—C9	1.319 (4)
N2—H2A	0.8600	C21—N6	1.323 (4)
O4—C17	1.227 (3)	C21—C20	1.365 (4)
N4—C16	1.269 (3)	C21—H21A	0.9300
N4—N5	1.382 (2)	C11—C10	1.374 (4)
N5—C17	1.343 (3)	C11—H11A	0.9300
N5—H5A	0.8600	N6—C22	1.337 (3)
C6—O2	1.224 (3)	C14—C13	1.401 (4)
C6—C7	1.482 (3)	C14—H14A	0.9300
C17—C18	1.492 (3)	C19—C20	1.374 (4)
O1—C4	1.363 (3)	C19—H19A	0.9300
O1—C1	1.363 (4)	C22—H22A	0.9300
C7—C8	1.374 (3)	C3—C2	1.409 (5)
C7—C11	1.380 (3)	C3—H3B	0.9300
O3—C15	1.363 (3)	C9—C10	1.360 (4)
O3—C12	1.363 (3)	C9—H9A	0.9300
C18—C19	1.377 (3)	C20—H20A	0.9300
C18—C22	1.386 (3)	C13—C12	1.315 (4)
C15—C14	1.341 (4)	C13—H13A	0.9300
C15—C16	1.433 (3)	C12—H12A	0.9300
C5—C4	1.432 (4)	C1—C2	1.327 (5)
C5—H5B	0.9300	C1—H1B	0.9300
C16—H16A	0.9300	C10—H10A	0.9300
C4—C3	1.346 (4)	C2—H2B	0.9300

C5—N1—N2	115.95 (18)	N6—C21—H21A	118.0
C6—N2—N1	119.08 (17)	C20—C21—H21A	118.0
C6—N2—H2A	120.5	C10—C11—C7	119.5 (2)
N1—N2—H2A	120.5	C10—C11—H11A	120.3
C16—N4—N5	114.65 (17)	C7—C11—H11A	120.3
C17—N5—N4	119.75 (17)	C21—N6—C22	116.5 (2)
C17—N5—H5A	120.1	C15—C14—C13	107.2 (3)
N4—N5—H5A	120.1	C15—C14—H14A	126.4
O2—C6—N2	122.4 (2)	C13—C14—H14A	126.4
O2—C6—C7	120.7 (2)	C20—C19—C18	119.5 (2)
N2—C6—C7	116.88 (18)	C20—C19—H19A	120.3
O4—C17—N5	122.6 (2)	C18—C19—H19A	120.3
O4—C17—C18	121.7 (2)	N6—C22—C18	124.3 (2)
N5—C17—C18	115.71 (18)	N6—C22—H22A	117.8
C4—O1—C1	105.7 (2)	C18—C22—H22A	117.8
C8—C7—C11	117.3 (2)	C4—C3—C2	106.9 (3)
C8—C7—C6	123.6 (2)	C4—C3—H3B	126.5
C11—C7—C6	119.08 (19)	C2—C3—H3B	126.5
C15—O3—C12	105.9 (2)	N3—C9—C10	124.3 (3)
C19—C18—C22	117.0 (2)	N3—C9—H9A	117.8
C19—C18—C17	119.9 (2)	C10—C9—H9A	117.8
C22—C18—C17	123.1 (2)	C21—C20—C19	118.8 (2)
C14—C15—O3	109.3 (2)	C21—C20—H20A	120.6
C14—C15—C16	131.3 (2)	C19—C20—H20A	120.6
O3—C15—C16	119.4 (2)	C12—C13—C14	106.7 (2)
N1—C5—C4	121.1 (2)	C12—C13—H13A	126.7
N1—C5—H5B	119.5	C14—C13—H13A	126.7
C4—C5—H5B	119.5	C13—C12—O3	110.9 (3)
N4—C16—C15	122.9 (2)	C13—C12—H12A	124.5
N4—C16—H16A	118.6	O3—C12—H12A	124.5
C15—C16—H16A	118.6	C2—C1—O1	111.3 (3)
C3—C4—O1	109.9 (2)	C2—C1—H1B	124.4
C3—C4—C5	131.7 (3)	O1—C1—H1B	124.4
O1—C4—C5	118.4 (2)	C9—C10—C11	118.1 (3)
N3—C8—C7	124.0 (2)	C9—C10—H10A	121.0
N3—C8—H8A	118.0	C11—C10—H10A	121.0
C7—C8—H8A	118.0	C1—C2—C3	106.2 (3)
C9—N3—C8	116.8 (2)	C1—C2—H2B	126.9
N6—C21—C20	123.9 (2)	C3—C2—H2B	126.9

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O4ⁱ	0.86	2.26	3.080 (2)	161
N2—H2A···N4ⁱ	0.86	2.51	3.112 (3)	128
N5—H5A···O2ⁱⁱ	0.86	2.01	2.843 (3)	162
C8—H8A···O4ⁱ	0.93	2.56	3.433 (3)	156
C16—H16A···O2ⁱⁱ	0.93	2.45	3.228 (3)	141
C22—H22A···O2ⁱⁱ	0.93	2.43	3.260 (3)	149

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

Experimental details

Crystal data
Chemical formula	C₁₁H₉N₃O₂
M_r	215.21
Crystal system, space group	Monoclinic, Cc
Temperature (K)	296
a, b, c (Å)	17.4363 (3), 16.9143 (3), 7.9639 (1)
β (°)	115.326 (1)
V (Å³)	2122.99 (6)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.34 × 0.24 × 0.15

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1998)
T_min, T_max	0.964, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections	9336, 2443, 1908
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.086, 1.06
No. of reflections	2443
No. of parameters	290
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.10, −0.16

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), 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—H2A···O4ⁱ	0.86	2.26	3.080 (2)	161
N2—H2A···N4ⁱ	0.86	2.51	3.112 (3)	128
N5—H5A···O2ⁱⁱ	0.86	2.01	2.843 (3)	162
C8—H8A···O4ⁱ	0.93	2.56	3.433 (3)	156
C16—H16A···O2ⁱⁱ	0.93	2.45	3.228 (3)	141
C22—H22A···O2ⁱⁱ	0.93	2.43	3.260 (3)	149

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

Acknowledgements

The authors would like to express their deep appreciation to the Startup Fund for PhDs of the Natural Scientific Research of Zhengzhou University of Light Industry (No.2005001) and the Fund for Natural Scientific Research of Zhengzhou University of Light Industry (000455).

References

Bruker (1998). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Kahwa, I. A., Selbin, I., Hsieh, T. C. Y. & Laine, R. A. (1986). Inorg. Chim. Acta, 118, 179–185. CrossRef CAS Web of Science Google Scholar
Santos, M. L. P., Bagatin, I. A., Pereira, E. M. & Ferreira, A. M. D. C. (2001). J. Chem. Soc. Dalton Trans. pp. 838-844. Web of Science CrossRef Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar