(E)-N′-(3-Chloro­benzyl­idene)isonicotinohydrazide

The mol­ecule of the title compound, C₁₃H₉ClN₃O, is roughly planar and displays a trans configuration with respect to the C=N double bond. The dihedral angle between the benzene and pyridine rings is 4.8 (3)°. The crystal structure is stabilized by inter­molecular N—H...N hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C)= 0.004 Å
• R factor = 0.061
• wR factor = 0.169
• Data-to-parameter ratio = 15.2

checkCIF/PLATON results

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

(E)—N'-(3-Chlorobenzylidene)isonicotinohydrazide

Crystal data

C13H10ClN3O	F(000) = 536
Mr = 259.69	Dx = 1.419 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1856 reflections
a = 7.6299 (3) Å	θ = 4.2–26°
b = 11.3388 (5) Å	µ = 0.30 mm^−1
c = 14.4189 (6) Å	T = 298 K
β = 102.979 (2)°	Block, colourless
V = 1215.57 (9) Å^3	0.46 × 0.08 × 0.06 mm
Z = 4

Data collection

Bruker SMART APEX area-detector diffractometer	2475 independent reflections
Radiation source: fine-focus sealed tube	1336 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.042
ω scans	θmax = 26.4°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→7
Tmin = 0.954, Tmax = 0.975	k = −14→14
6893 measured reflections	l = −18→15

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.169	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0682P)^2 + 0.2543P] where P = (Fo^2 + 2Fc^2)/3
2475 reflections	(Δ/σ)max < 0.001
163 parameters	Δρmax = 0.34 e Å^−3
0 restraints	Δρmin = −0.29 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.00310 (19)	1.10388 (10)	0.11527 (7)	0.1051 (5)
O1	0.0123 (4)	0.7157 (2)	0.46177 (15)	0.0750 (8)
N1	0.1631 (4)	0.5262 (2)	0.78208 (17)	0.0503 (7)
C1	0.2471 (4)	1.0986 (2)	0.3898 (2)	0.0433 (8)
N2	0.1823 (3)	0.8595 (2)	0.54582 (16)	0.0440 (7)
H2A	0.2408	0.8852	0.6001	0.053*
C2	0.1404 (5)	1.0687 (3)	0.3013 (2)	0.0493 (8)
H2	0.0726	0.9998	0.2938	0.059*
N3	0.1701 (3)	0.9249 (2)	0.46415 (17)	0.0459 (7)
C3	0.1366 (5)	1.1425 (3)	0.2252 (2)	0.0594 (10)
C4	0.2340 (6)	1.2467 (3)	0.2339 (3)	0.0636 (10)
H4	0.2299	1.2957	0.1817	0.076*
C5	0.3366 (5)	1.2752 (3)	0.3218 (3)	0.0678 (11)
H5	0.4021	1.3451	0.3290	0.081*
C6	0.3456 (5)	1.2032 (3)	0.4000 (3)	0.0578 (9)
H6	0.4167	1.2243	0.4588	0.069*
C7	0.2554 (4)	1.0227 (3)	0.4726 (2)	0.0473 (8)
H7	0.3231	1.0457	0.5317	0.057*
C8	0.0984 (4)	0.7530 (3)	0.5376 (2)	0.0460 (8)
C9	0.1194 (4)	0.6811 (2)	0.62660 (19)	0.0381 (7)
C10	0.0285 (4)	0.5744 (3)	0.6204 (2)	0.0488 (8)
H10	−0.0496	0.5525	0.5638	0.059*
C11	0.0541 (4)	0.5015 (3)	0.6979 (2)	0.0508 (8)
H11	−0.0081	0.4304	0.6917	0.061*
C12	0.2467 (5)	0.6296 (3)	0.7882 (2)	0.0522 (9)
H12	0.3215	0.6500	0.8463	0.063*
C13	0.2297 (4)	0.7089 (3)	0.7140 (2)	0.0470 (8)
H13	0.2916	0.7802	0.7226	0.056*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.1551 (13)	0.0936 (9)	0.0515 (6)	−0.0003 (8)	−0.0086 (7)	0.0175 (6)
O1	0.120 (2)	0.0529 (14)	0.0377 (13)	−0.0242 (14)	−0.0123 (14)	0.0053 (11)
N1	0.0645 (19)	0.0429 (15)	0.0405 (15)	−0.0024 (14)	0.0054 (14)	0.0068 (12)
C1	0.053 (2)	0.0375 (16)	0.0424 (18)	0.0036 (15)	0.0177 (16)	−0.0001 (13)
N2	0.0607 (18)	0.0405 (14)	0.0282 (13)	−0.0029 (12)	0.0043 (12)	0.0015 (10)
C2	0.065 (2)	0.0372 (16)	0.048 (2)	0.0028 (15)	0.0173 (17)	0.0041 (14)
N3	0.0595 (19)	0.0430 (15)	0.0349 (14)	0.0016 (13)	0.0097 (13)	0.0041 (11)
C3	0.078 (3)	0.055 (2)	0.047 (2)	0.0147 (19)	0.0186 (19)	0.0090 (16)
C4	0.089 (3)	0.047 (2)	0.063 (2)	0.0111 (19)	0.034 (2)	0.0200 (17)
C5	0.085 (3)	0.044 (2)	0.081 (3)	−0.0037 (19)	0.034 (2)	0.0085 (19)
C6	0.068 (3)	0.047 (2)	0.063 (2)	−0.0017 (17)	0.0239 (19)	−0.0001 (16)
C7	0.058 (2)	0.0448 (18)	0.0396 (17)	−0.0020 (16)	0.0120 (16)	−0.0015 (14)
C8	0.060 (2)	0.0377 (17)	0.0365 (18)	0.0007 (15)	0.0027 (16)	0.0001 (13)
C9	0.0471 (19)	0.0347 (15)	0.0307 (15)	0.0042 (14)	0.0049 (14)	−0.0010 (12)
C10	0.057 (2)	0.0445 (18)	0.0387 (18)	−0.0073 (15)	−0.0030 (16)	−0.0014 (14)
C11	0.061 (2)	0.0408 (17)	0.0463 (19)	−0.0093 (15)	0.0040 (18)	0.0043 (14)
C12	0.065 (2)	0.0481 (19)	0.0361 (17)	−0.0016 (17)	−0.0035 (16)	−0.0007 (14)
C13	0.057 (2)	0.0368 (16)	0.0423 (18)	−0.0049 (15)	0.0009 (16)	0.0007 (14)

Geometric parameters (Å, º)

Cl1—C3	1.737 (4)	C4—H4	0.9300
O1—C8	1.218 (3)	C5—C6	1.381 (4)
N1—C12	1.329 (4)	C5—H5	0.9300
N1—C11	1.338 (4)	C6—H6	0.9300
C1—C2	1.392 (4)	C7—H7	0.9300
C1—C6	1.394 (4)	C8—C9	1.498 (4)
C1—C7	1.462 (4)	C9—C13	1.386 (4)
N2—C8	1.359 (4)	C9—C10	1.388 (4)
N2—N3	1.377 (3)	C10—C11	1.368 (4)
N2—H2A	0.8600	C10—H10	0.9300
C2—C3	1.374 (4)	C11—H11	0.9300
C2—H2	0.9300	C12—C13	1.381 (4)
N3—C7	1.277 (4)	C12—H12	0.9300
C3—C4	1.387 (5)	C13—H13	0.9300
C4—C5	1.370 (5)
C12—N1—C11	115.9 (3)	C1—C6—H6	120.3
C2—C1—C6	119.6 (3)	N3—C7—C1	120.4 (3)
C2—C1—C7	120.9 (3)	N3—C7—H7	119.8
C6—C1—C7	119.4 (3)	C1—C7—H7	119.8
C8—N2—N3	117.6 (2)	O1—C8—N2	122.4 (3)
C8—N2—H2A	121.2	O1—C8—C9	120.8 (3)
N3—N2—H2A	121.2	N2—C8—C9	116.8 (3)
C3—C2—C1	119.1 (3)	C13—C9—C10	116.7 (3)
C3—C2—H2	120.5	C13—C9—C8	125.6 (3)
C1—C2—H2	120.5	C10—C9—C8	117.6 (3)
C7—N3—N2	116.8 (3)	C11—C10—C9	119.8 (3)
C2—C3—C4	122.1 (3)	C11—C10—H10	120.1
C2—C3—Cl1	118.5 (3)	C9—C10—H10	120.1
C4—C3—Cl1	119.3 (3)	N1—C11—C10	124.1 (3)
C5—C4—C3	117.9 (3)	N1—C11—H11	118.0
C5—C4—H4	121.1	C10—C11—H11	118.0
C3—C4—H4	121.1	N1—C12—C13	124.3 (3)
C4—C5—C6	122.0 (3)	N1—C12—H12	117.9
C4—C5—H5	119.0	C13—C12—H12	117.9
C6—C5—H5	119.0	C12—C13—C9	119.2 (3)
C5—C6—C1	119.3 (3)	C12—C13—H13	120.4
C5—C6—H6	120.3	C9—C13—H13	120.4
C6—C1—C2—C3	1.0 (5)	N3—N2—C8—O1	−1.2 (5)
C7—C1—C2—C3	−179.9 (3)	N3—N2—C8—C9	177.6 (2)
C8—N2—N3—C7	−177.4 (3)	O1—C8—C9—C13	172.5 (3)
C1—C2—C3—C4	−0.8 (5)	N2—C8—C9—C13	−6.3 (5)
C1—C2—C3—Cl1	179.9 (2)	O1—C8—C9—C10	−3.9 (5)
C2—C3—C4—C5	0.1 (5)	N2—C8—C9—C10	177.3 (3)
Cl1—C3—C4—C5	179.4 (3)	C13—C9—C10—C11	−1.7 (5)
C3—C4—C5—C6	0.5 (6)	C8—C9—C10—C11	175.1 (3)
C4—C5—C6—C1	−0.3 (5)	C12—N1—C11—C10	1.2 (5)
C2—C1—C6—C5	−0.4 (5)	C9—C10—C11—N1	0.3 (5)
C7—C1—C6—C5	−179.5 (3)	C11—N1—C12—C13	−1.3 (5)
N2—N3—C7—C1	−178.9 (3)	N1—C12—C13—C9	−0.1 (5)
C2—C1—C7—N3	2.8 (4)	C10—C9—C13—C12	1.6 (4)
C6—C1—C7—N3	−178.0 (3)	C8—C9—C13—C12	−174.9 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···N1^i	0.86	2.33	3.131 (3)	156

Symmetry code: (i) −x+1/2, y+1/2, −z+3/2.