N′-(5-Chloro-2-hydroxy­benzyl­idene)nicotinohydrazide

Ren, C.-G.

doi:10.1107/S1600536809020819

organic compounds

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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Pages o1505-o1506

doi:10.1107/S1600536809020819

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N′-(5-Chloro-2-hydroxybenzylidene)nicotinohydrazide

Chong-Gui Ren ^a ^*

^aDepartment of Chemistry and Chemical Engineering, Zaozhuang University, Zaozhuang Shandong 277160, People's Republic of China
^*Correspondence e-mail: renchonggui@163.com

(Received 25 May 2009; accepted 2 June 2009; online 6 June 2009)

There are two independent Schiff base molecules in the asymmetric unit of the title compound, C₁₃H₁₀ClN₃O₂. The dihedral angles between the benzene and pyridine rings are 12.8 (2) and 1.9 (2)° in the two molecules. Intramolecular O—H⋯N hydrogen bonds are observed. Molecules are linked into centrosymmetric R⁴₄(26) motifs by N—H⋯O and N—H⋯N interactions.

Related literature

For the biological properties of Schiff base compounds, see: Jeewoth et al. (1999 ); Ren et al. (2002 ); Eltayeb et al. (2008 ); Sinha et al. (2008 ). For metal complexes of Schiff base compounds, see: Shivakumar et al. (2008 ); Prabhakaran et al. (2006 ); Dhar et al. (2005 ). For related structures, see: Cui et al. (2007 ); Jing et al. (2007 ); Ma et al. (2008 ); Salhin et al. (2007 ); Lin et al. (2007 ); Alhadi et al. (2008 ); Xue et al. (2008 ); Wang et al. (2008 ); Lu (2008 ); Diao et al. (2008 ); Qiu (2009 ); Mohd Lair et al. (2009a ,b ). For reference structural data, see: Allen et al. (1987 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₃H₁₀ClN₃O₂
M_r = 275.69
Monoclinic, P 2₁ /n
a = 9.792 (2) Å
b = 23.358 (3) Å
c = 10.926 (2) Å
β = 96.848 (2)°
V = 2481.2 (8) Å³
Z = 8
Mo Kα radiation
μ = 0.31 mm⁻¹
T = 298 K
0.30 × 0.30 × 0.27 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.913, T_max = 0.921
14387 measured reflections
5342 independent reflections
3193 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.115
S = 1.01
5342 reflections
351 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.88	2.594 (2)	145
O3—H3⋯N4	0.82	1.82	2.538 (2)	146
N5—H5⋯N3ⁱ	0.891 (10)	2.109 (11)	2.991 (3)	171 (2)
N2—H2⋯O3	0.892 (10)	2.097 (10)	2.984 (2)	173 (2)
Symmetry code: (i) -x+1, -y, -z+2.

Data collection: SMART (Bruker, 2002 ); cell refinement: SAINT (Bruker, 2002); 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809020819/bx2215sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809020819/bx2215Isup2.hkl

checkCIF report

Comment top

The Schiff base compounds show excellent biological properties (Jeewoth et al., 1999; Ren et al., 2002; Eltayeb et al., 2008; Sinha et al., 2008). Moreover, the Schiff base compounds have been widely used as versatile ligands in coordination chemistry (Shivakumar et al., 2008; Prabhakaran et al., 2006; Dhar et al., 2005). We report here the crystal structure of the title compound .In the title compound, Fig. 1, there two independent molecules in the symmetric unit.The dihedral angles between the benzene and pyridine rings are 12.8 (2) and 1.9 (2)°, respectively. All the bond lengths are within normal values (Allen et al., 1987) and comparable to those in other similar compounds (Cui et al., 2007; Jing et al., 2007; Ma et al., 2008; Salhin et al., 2007; Lin et al., 2007; Alhadi et al., 2008; Xue et al., 2008; Wang et al., 2008; Lu, 2008; Diao et al., 2008; Qiu, 2009; Lair et al., 2009a,b). The molecules of the title compound are linked into centrosymmetric R⁴₄(26) motifs by N–H···O and N–H···N interactions (Table 1, Fig. 2) (Bernstein et al., 1995).

Related literature top

For the biological properties of Schiff base compounds, see: Jeewoth et al. (1999); Ren et al. (2002); Eltayeb et al. (2008); Sinha et al. (2008). For metal complexes of Schiff base compounds, see: Shivakumar et al. (2008); Prabhakaran et al. (2006); Dhar et al. (2005). For related structures, see: Cui et al. (2007); Jing et al. (2007); Ma et al. (2008); Salhin et al. (2007); Lin et al. (2007); Alhadi et al. (2008); Xue et al. (2008); Wang et al. (2008); Lu (2008); Diao et al. (2008); Qiu (2009); Mohd Lair et al. (2009a,b). For reference structural data, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

All the starting materials were obtained with AR grade from Lancaster. 5-Chloro-2-hydroxybenzaldehyde (1.0 mmol, 157.1 mg) and nicotinohydrazide (1.0 mmol, 137.1 mg) were refluxed in a 30 ml methanol solution for 30 min to give a clear yellow solution. Yellow block-shaped single crystals of the compound were obtained by slow evaporation of the solution for five days at room temperature.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the compound with 30% probability ellipsoids. The intramolecular O–H···N hydrogen bonds are shown as dashed lines.
	Fig. 2. Molecular packing of the compound with hydrogen bonds drawn as dashed lines. Hydrogen atoms not involved in hydrogen bonding have been omitted.

(I) top

Crystal data top

C₁₃H₁₀ClN₃O₂	F(000) = 1136
M_r = 275.69	D_x = 1.476 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2236 reflections
a = 9.792 (2) Å	θ = 2.6–24.5°
b = 23.358 (3) Å	µ = 0.31 mm⁻¹
c = 10.926 (2) Å	T = 298 K
β = 96.848 (2)°	Block, yellow
V = 2481.2 (8) Å³	0.30 × 0.30 × 0.27 mm
Z = 8

Data collection top

Bruker SMART CCD area-detector diffractometer	5342 independent reflections
Radiation source: fine-focus sealed tube	3193 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
ω scans	θ_max = 27.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
T_min = 0.913, T_max = 0.921	k = −29→27
14387 measured reflections	l = −12→13

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.0466P)²] where P = (F_o² + 2F_c²)/3
5342 reflections	(Δ/σ)_max < 0.001
351 parameters	Δρ_max = 0.22 e Å⁻³
2 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₃H₁₀ClN₃O₂	V = 2481.2 (8) Å³
M_r = 275.69	Z = 8
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.792 (2) Å	µ = 0.31 mm⁻¹
b = 23.358 (3) Å	T = 298 K
c = 10.926 (2) Å	0.30 × 0.30 × 0.27 mm
β = 96.848 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	5342 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3193 reflections with I > 2σ(I)
T_min = 0.913, T_max = 0.921	R_int = 0.042
14387 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	2 restraints
wR(F²) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.22 e Å⁻³
5342 reflections	Δρ_min = −0.24 e Å⁻³
351 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
Cl1	−0.31666 (7)	0.15824 (3)	0.49570 (7)	0.0648 (2)
Cl2	0.67723 (7)	−0.10226 (3)	0.57393 (6)	0.0648 (2)
N1	0.28860 (19)	0.22587 (8)	0.70899 (16)	0.0414 (5)
N2	0.4128 (2)	0.20261 (8)	0.75424 (18)	0.0421 (5)
N3	0.7948 (2)	0.13722 (8)	0.92250 (17)	0.0438 (5)
N4	0.29718 (18)	0.00154 (8)	0.94498 (16)	0.0387 (4)
N5	0.2156 (2)	−0.01091 (8)	1.03441 (16)	0.0402 (5)
N6	−0.0434 (2)	−0.04219 (10)	1.3111 (2)	0.0659 (6)
O1	0.13564 (17)	0.31528 (6)	0.65672 (16)	0.0520 (4)
H1	0.2075	0.2981	0.6784	0.078*
O2	0.50725 (19)	0.29034 (7)	0.76057 (19)	0.0755 (6)
O3	0.39503 (17)	0.07872 (6)	0.81707 (15)	0.0486 (4)
H3	0.3484	0.0658	0.8682	0.073*
O4	0.17570 (18)	0.08396 (7)	1.05029 (15)	0.0598 (5)
C1	0.0545 (2)	0.21766 (9)	0.63088 (19)	0.0368 (5)
C2	0.0344 (2)	0.27712 (9)	0.62187 (19)	0.0394 (5)
C3	−0.0937 (3)	0.29868 (10)	0.5765 (2)	0.0496 (6)
H3A	−0.1072	0.3381	0.5715	0.059*
C4	−0.2008 (3)	0.26227 (11)	0.5390 (2)	0.0504 (6)
H4	−0.2865	0.2770	0.5088	0.060*
C5	−0.1810 (2)	0.20380 (10)	0.5461 (2)	0.0438 (6)
C6	−0.0555 (2)	0.18151 (10)	0.59222 (19)	0.0415 (6)
H6	−0.0439	0.1420	0.5977	0.050*
C7	0.1862 (2)	0.19285 (10)	0.6792 (2)	0.0411 (6)
H7	0.1957	0.1534	0.6882	0.049*
C8	0.5195 (2)	0.23961 (10)	0.7816 (2)	0.0444 (6)
C9	0.6530 (2)	0.21501 (9)	0.83757 (19)	0.0359 (5)
C10	0.7653 (3)	0.25086 (10)	0.8548 (2)	0.0483 (6)
H10	0.7567	0.2890	0.8304	0.058*
C11	0.8900 (3)	0.23037 (11)	0.9080 (2)	0.0585 (7)
H11	0.9658	0.2545	0.9224	0.070*
C12	0.9001 (3)	0.17355 (11)	0.9395 (2)	0.0509 (6)
H12	0.9849	0.1597	0.9746	0.061*
C13	0.6739 (2)	0.15881 (9)	0.8743 (2)	0.0425 (6)
H13	0.5985	0.1343	0.8649	0.051*
C14	0.4402 (2)	−0.02227 (9)	0.79497 (18)	0.0357 (5)
C15	0.4588 (2)	0.03497 (9)	0.7643 (2)	0.0380 (5)
C16	0.5456 (2)	0.04896 (10)	0.6773 (2)	0.0476 (6)
H16	0.5579	0.0872	0.6572	0.057*
C17	0.6134 (2)	0.00709 (10)	0.6205 (2)	0.0464 (6)
H17	0.6724	0.0169	0.5632	0.056*
C18	0.5936 (2)	−0.04957 (10)	0.6489 (2)	0.0446 (6)
C19	0.5080 (2)	−0.06441 (9)	0.7344 (2)	0.0414 (6)
H19	0.4951	−0.1028	0.7523	0.050*
C20	0.3537 (2)	−0.03840 (9)	0.88893 (19)	0.0395 (5)
H20	0.3400	−0.0767	0.9076	0.047*
C21	0.1567 (2)	0.03509 (10)	1.0846 (2)	0.0419 (6)
C22	0.0660 (2)	0.02299 (9)	1.18211 (19)	0.0401 (5)
C23	0.0067 (3)	0.06862 (11)	1.2362 (2)	0.0538 (7)
H23	0.0236	0.1059	1.2124	0.065*
C24	−0.0774 (3)	0.05834 (13)	1.3256 (2)	0.0651 (8)
H24	−0.1193	0.0885	1.3624	0.078*
C25	−0.0986 (3)	0.00294 (14)	1.3595 (2)	0.0657 (8)
H25	−0.1554	−0.0034	1.4206	0.079*
C26	0.0382 (3)	−0.03068 (10)	1.2238 (2)	0.0542 (7)
H26	0.0790	−0.0616	1.1887	0.065*
H5	0.206 (3)	−0.0477 (5)	1.053 (2)	0.080*
H2	0.411 (3)	0.1663 (5)	0.779 (2)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0444 (4)	0.0649 (5)	0.0827 (5)	−0.0128 (3)	−0.0025 (4)	0.0037 (4)
Cl2	0.0697 (5)	0.0567 (4)	0.0709 (5)	0.0172 (4)	0.0197 (4)	−0.0037 (3)
N1	0.0369 (12)	0.0387 (11)	0.0479 (11)	0.0041 (9)	0.0020 (9)	0.0047 (9)
N2	0.0351 (12)	0.0342 (11)	0.0552 (12)	0.0012 (9)	−0.0016 (10)	0.0047 (9)
N3	0.0362 (12)	0.0371 (11)	0.0574 (13)	0.0001 (9)	0.0023 (10)	0.0029 (9)
N4	0.0374 (12)	0.0354 (11)	0.0432 (11)	−0.0026 (9)	0.0048 (9)	0.0047 (9)
N5	0.0422 (12)	0.0333 (11)	0.0465 (11)	0.0001 (9)	0.0116 (10)	0.0040 (9)
N6	0.0726 (17)	0.0628 (15)	0.0674 (15)	0.0088 (13)	0.0299 (13)	0.0101 (12)
O1	0.0514 (11)	0.0317 (9)	0.0697 (11)	−0.0002 (8)	−0.0060 (10)	0.0021 (8)
O2	0.0604 (13)	0.0346 (11)	0.1240 (16)	−0.0032 (9)	−0.0194 (12)	0.0196 (10)
O3	0.0549 (11)	0.0292 (9)	0.0649 (11)	−0.0015 (8)	0.0206 (9)	0.0034 (7)
O4	0.0713 (13)	0.0321 (10)	0.0788 (12)	0.0011 (9)	0.0205 (10)	0.0045 (9)
C1	0.0369 (14)	0.0353 (13)	0.0390 (13)	0.0020 (10)	0.0073 (10)	0.0041 (10)
C2	0.0432 (15)	0.0366 (13)	0.0387 (13)	−0.0007 (11)	0.0057 (11)	0.0002 (10)
C3	0.0506 (17)	0.0368 (14)	0.0600 (16)	0.0088 (12)	0.0013 (13)	0.0051 (11)
C4	0.0419 (16)	0.0554 (17)	0.0527 (16)	0.0080 (13)	0.0008 (12)	0.0060 (12)
C5	0.0358 (15)	0.0476 (15)	0.0481 (14)	−0.0051 (11)	0.0056 (11)	0.0018 (11)
C6	0.0430 (15)	0.0354 (13)	0.0467 (14)	−0.0024 (11)	0.0079 (11)	0.0033 (10)
C7	0.0426 (15)	0.0326 (13)	0.0482 (14)	0.0022 (11)	0.0052 (12)	0.0025 (10)
C8	0.0445 (16)	0.0353 (14)	0.0523 (15)	0.0002 (11)	0.0012 (12)	0.0038 (11)
C9	0.0376 (14)	0.0289 (12)	0.0410 (12)	−0.0028 (10)	0.0042 (10)	−0.0003 (9)
C10	0.0498 (17)	0.0308 (13)	0.0635 (16)	−0.0067 (11)	0.0035 (13)	0.0037 (11)
C11	0.0433 (16)	0.0477 (16)	0.0815 (19)	−0.0131 (13)	−0.0043 (14)	0.0003 (14)
C12	0.0367 (15)	0.0520 (17)	0.0625 (16)	0.0016 (12)	0.0000 (12)	0.0000 (12)
C13	0.0338 (14)	0.0358 (13)	0.0571 (15)	−0.0048 (11)	0.0027 (12)	0.0019 (11)
C14	0.0332 (13)	0.0330 (12)	0.0399 (13)	−0.0017 (10)	−0.0006 (10)	0.0050 (10)
C15	0.0335 (13)	0.0355 (13)	0.0444 (13)	−0.0027 (10)	0.0020 (11)	0.0005 (10)
C16	0.0530 (16)	0.0365 (14)	0.0542 (15)	−0.0072 (12)	0.0097 (13)	0.0051 (11)
C17	0.0454 (16)	0.0496 (15)	0.0457 (14)	−0.0044 (12)	0.0121 (12)	0.0040 (12)
C18	0.0449 (15)	0.0427 (14)	0.0455 (14)	0.0065 (11)	0.0029 (12)	0.0007 (11)
C19	0.0445 (15)	0.0330 (13)	0.0459 (13)	0.0020 (11)	0.0025 (11)	0.0062 (10)
C20	0.0417 (14)	0.0281 (12)	0.0482 (14)	−0.0016 (10)	0.0037 (11)	0.0049 (10)
C21	0.0393 (14)	0.0365 (14)	0.0484 (14)	−0.0008 (11)	−0.0004 (11)	−0.0002 (11)
C22	0.0367 (14)	0.0385 (14)	0.0439 (13)	0.0042 (10)	0.0005 (11)	−0.0027 (10)
C23	0.0542 (17)	0.0453 (15)	0.0622 (17)	0.0041 (13)	0.0073 (14)	−0.0108 (12)
C24	0.0600 (19)	0.068 (2)	0.0687 (19)	0.0135 (15)	0.0139 (15)	−0.0213 (15)
C25	0.0514 (18)	0.094 (2)	0.0538 (17)	0.0100 (17)	0.0166 (14)	−0.0020 (16)
C26	0.0606 (18)	0.0439 (16)	0.0619 (16)	0.0083 (13)	0.0230 (14)	−0.0006 (12)

Geometric parameters (Å, º) top

Cl1—C5	1.740 (2)	C7—H7	0.9300
Cl2—C18	1.736 (2)	C8—C9	1.491 (3)
N1—C7	1.276 (3)	C9—C10	1.376 (3)
N1—N2	1.369 (2)	C9—C13	1.381 (3)
N2—C8	1.361 (3)	C10—C11	1.375 (3)
N2—H2	0.892 (10)	C10—H10	0.9300
N3—C12	1.332 (3)	C11—C12	1.372 (3)
N3—C13	1.336 (3)	C11—H11	0.9300
N4—C20	1.278 (3)	C12—H12	0.9300
N4—N5	1.365 (2)	C13—H13	0.9300
N5—C21	1.365 (3)	C14—C15	1.396 (3)
N5—H5	0.891 (10)	C14—C19	1.397 (3)
N6—C25	1.324 (3)	C14—C20	1.456 (3)
N6—C26	1.342 (3)	C15—C16	1.388 (3)
O1—C2	1.354 (3)	C16—C17	1.371 (3)
O1—H1	0.8200	C16—H16	0.9300
O2—C8	1.210 (2)	C17—C18	1.378 (3)
O3—C15	1.361 (2)	C17—H17	0.9300
O3—H3	0.8200	C18—C19	1.373 (3)
O4—C21	1.223 (2)	C19—H19	0.9300
C1—C6	1.394 (3)	C20—H20	0.9300
C1—C2	1.405 (3)	C21—C22	1.493 (3)
C1—C7	1.455 (3)	C22—C26	1.372 (3)
C2—C3	1.387 (3)	C22—C23	1.380 (3)
C3—C4	1.375 (3)	C23—C24	1.372 (3)
C3—H3A	0.9300	C23—H23	0.9300
C4—C5	1.380 (3)	C24—C25	1.369 (4)
C4—H4	0.9300	C24—H24	0.9300
C5—C6	1.374 (3)	C25—H25	0.9300
C6—H6	0.9300	C26—H26	0.9300

C7—N1—N2	119.29 (19)	N3—C12—C11	123.3 (2)
C8—N2—N1	116.92 (19)	N3—C12—H12	118.3
C8—N2—H2	125.2 (17)	C11—C12—H12	118.3
N1—N2—H2	116.2 (18)	N3—C13—C9	124.5 (2)
C12—N3—C13	116.7 (2)	N3—C13—H13	117.7
C20—N4—N5	120.75 (18)	C9—C13—H13	117.7
C21—N5—N4	115.52 (18)	C15—C14—C19	118.6 (2)
C21—N5—H5	127.1 (17)	C15—C14—C20	121.4 (2)
N4—N5—H5	117.4 (17)	C19—C14—C20	120.05 (19)
C25—N6—C26	115.5 (2)	O3—C15—C16	117.57 (19)
C2—O1—H1	109.5	O3—C15—C14	122.55 (19)
C15—O3—H3	109.5	C16—C15—C14	119.9 (2)
C6—C1—C2	118.8 (2)	C17—C16—C15	120.7 (2)
C6—C1—C7	119.2 (2)	C17—C16—H16	119.6
C2—C1—C7	122.0 (2)	C15—C16—H16	119.6
O1—C2—C3	117.5 (2)	C16—C17—C18	119.7 (2)
O1—C2—C1	122.7 (2)	C16—C17—H17	120.2
C3—C2—C1	119.8 (2)	C18—C17—H17	120.2
C4—C3—C2	120.5 (2)	C19—C18—C17	120.6 (2)
C4—C3—H3A	119.8	C19—C18—Cl2	120.18 (18)
C2—C3—H3A	119.8	C17—C18—Cl2	119.23 (18)
C3—C4—C5	119.9 (2)	C18—C19—C14	120.5 (2)
C3—C4—H4	120.1	C18—C19—H19	119.7
C5—C4—H4	120.1	C14—C19—H19	119.7
C6—C5—C4	120.6 (2)	N4—C20—C14	118.06 (19)
C6—C5—Cl1	120.01 (19)	N4—C20—H20	121.0
C4—C5—Cl1	119.37 (19)	C14—C20—H20	121.0
C5—C6—C1	120.4 (2)	O4—C21—N5	121.7 (2)
C5—C6—H6	119.8	O4—C21—C22	121.3 (2)
C1—C6—H6	119.8	N5—C21—C22	116.94 (19)
N1—C7—C1	119.2 (2)	C26—C22—C23	116.9 (2)
N1—C7—H7	120.4	C26—C22—C21	124.6 (2)
C1—C7—H7	120.4	C23—C22—C21	118.4 (2)
O2—C8—N2	121.6 (2)	C24—C23—C22	119.3 (2)
O2—C8—C9	121.2 (2)	C24—C23—H23	120.4
N2—C8—C9	117.3 (2)	C22—C23—H23	120.4
C10—C9—C13	116.8 (2)	C25—C24—C23	118.8 (2)
C10—C9—C8	117.9 (2)	C25—C24—H24	120.6
C13—C9—C8	125.3 (2)	C23—C24—H24	120.6
C11—C10—C9	120.0 (2)	N6—C25—C24	124.2 (3)
C11—C10—H10	120.0	N6—C25—H25	117.9
C9—C10—H10	120.0	C24—C25—H25	117.9
C12—C11—C10	118.5 (2)	N6—C26—C22	125.3 (2)
C12—C11—H11	120.8	N6—C26—H26	117.4
C10—C11—H11	120.8	C22—C26—H26	117.4

C7—N1—N2—C8	178.3 (2)	C8—C9—C13—N3	178.8 (2)
C20—N4—N5—C21	−177.7 (2)	C19—C14—C15—O3	178.9 (2)
C6—C1—C2—O1	−179.7 (2)	C20—C14—C15—O3	−2.0 (3)
C7—C1—C2—O1	0.3 (3)	C19—C14—C15—C16	−1.3 (3)
C6—C1—C2—C3	0.8 (3)	C20—C14—C15—C16	177.9 (2)
C7—C1—C2—C3	−179.2 (2)	O3—C15—C16—C17	179.9 (2)
O1—C2—C3—C4	179.7 (2)	C14—C15—C16—C17	0.1 (3)
C1—C2—C3—C4	−0.7 (3)	C15—C16—C17—C18	1.0 (4)
C2—C3—C4—C5	−0.2 (4)	C16—C17—C18—C19	−0.8 (4)
C3—C4—C5—C6	1.0 (3)	C16—C17—C18—Cl2	178.62 (18)
C3—C4—C5—Cl1	−178.88 (18)	C17—C18—C19—C14	−0.5 (3)
C4—C5—C6—C1	−1.0 (3)	Cl2—C18—C19—C14	−179.87 (17)
Cl1—C5—C6—C1	178.92 (16)	C15—C14—C19—C18	1.5 (3)
C2—C1—C6—C5	0.1 (3)	C20—C14—C19—C18	−177.7 (2)
C7—C1—C6—C5	−179.9 (2)	N5—N4—C20—C14	−179.66 (18)
N2—N1—C7—C1	−179.88 (18)	C15—C14—C20—N4	−1.5 (3)
C6—C1—C7—N1	176.7 (2)	C19—C14—C20—N4	177.7 (2)
C2—C1—C7—N1	−3.3 (3)	N4—N5—C21—O4	0.5 (3)
N1—N2—C8—O2	−3.9 (3)	N4—N5—C21—C22	179.61 (18)
N1—N2—C8—C9	176.60 (18)	O4—C21—C22—C26	178.9 (2)
O2—C8—C9—C10	−5.6 (3)	N5—C21—C22—C26	−0.2 (3)
N2—C8—C9—C10	173.9 (2)	O4—C21—C22—C23	−2.0 (3)
O2—C8—C9—C13	174.2 (2)	N5—C21—C22—C23	178.9 (2)
N2—C8—C9—C13	−6.3 (3)	C26—C22—C23—C24	−1.1 (4)
C13—C9—C10—C11	−0.9 (3)	C21—C22—C23—C24	179.7 (2)
C8—C9—C10—C11	178.9 (2)	C22—C23—C24—C25	0.8 (4)
C9—C10—C11—C12	2.0 (4)	C26—N6—C25—C24	0.2 (4)
C13—N3—C12—C11	−1.3 (4)	C23—C24—C25—N6	−0.4 (4)
C10—C11—C12—N3	−0.8 (4)	C25—N6—C26—C22	−0.6 (4)
C12—N3—C13—C9	2.5 (3)	C23—C22—C26—N6	1.1 (4)
C10—C9—C13—N3	−1.3 (3)	C21—C22—C26—N6	−179.8 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.88	2.594 (2)	145
O3—H3···N4	0.82	1.82	2.538 (2)	146
N5—H5···N3ⁱ	0.89 (1)	2.11 (1)	2.991 (3)	171 (2)
N2—H2···O3	0.89 (1)	2.10 (1)	2.984 (2)	173 (2)

Symmetry code: (i) −x+1, −y, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₀ClN₃O₂
M_r	275.69
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	9.792 (2), 23.358 (3), 10.926 (2)
β (°)	96.848 (2)
V (Å³)	2481.2 (8)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.31
Crystal size (mm)	0.30 × 0.30 × 0.27

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.913, 0.921
No. of measured, independent and observed [I > 2σ(I)] reflections	14387, 5342, 3193
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.115, 1.01
No. of reflections	5342
No. of parameters	351
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.24

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), 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
O1—H1···N1	0.82	1.88	2.594 (2)	145.2
O3—H3···N4	0.82	1.82	2.538 (2)	145.5
N5—H5···N3ⁱ	0.891 (10)	2.109 (11)	2.991 (3)	171 (2)
N2—H2···O3	0.892 (10)	2.097 (10)	2.984 (2)	173 (2)

Symmetry code: (i) −x+1, −y, −z+2.

Acknowledgements

The author acknowledges Zaozhuang University for funding this study.

References

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