4-Chloro-N'-[(3Z)-2-oxo-2,3-di-hydro-1H-indol-3-yl-idene]benzohydrazide.

In the title compound, C15H10ClN3O2, the benzene ring is slightly twisted out of the plane of the 2,3-di-hydro-1H-indole ring system (r.m.s. deviation = 0.007 Å), forming a dihedral angle of 7.4 (3)°. An intra-molecular N-H⋯O hydrogen bond forms a six-membered ring. In the crystal, mol-ecules are linked via N-H⋯O and C-H⋯O hydrogen bonds, forming layers alternately perpendicular to [011] and [0-11].

Related literature

For the diverse bio-activities of acid hydrazides and their condensed products, see: Adekunle et al. (2012 ▶); Al-Assar et al. (2002 ▶); Dharmaraj et al. (2001 ▶); Jain & Vederas (2004 ▶); Jeeworth et al. (2000 ▶); Scozzafava et al. (2001 ▶); Siddappa et al. (2008 ▶); Strappaghetti et al. (2006 ▶).

Experimental

Crystal data

C15H10ClN3O2

M = 299.71

Orthorhombic,

a = 31.0359 (12) Å

b = 5.2549 (3) Å

c = 7.8730 (4) Å

V = 1284.01 (11) Å3

Z = 4

Cu Kα radiation

μ = 2.72 mm−1

T = 102 K

0.22 × 0.17 × 0.01 mm

Data collection

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2013 ▶) T min = 0.75, T max = 0.97

4190 measured reflections

1596 independent reflections

1434 reflections with I > 2σ(I)

R int = 0.109

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.152

S = 1.16

1596 reflections

193 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.37 e Å−3

Absolute structure: Flack (1983 ▶), 478 Friedal pairs (44% coverage)

Absolute structure parameter: −0.06 (5)

Data collection: APEX2 (Bruker, 2013 ▶); cell refinement: SAINT (Bruker, 2013 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813033345/su2672sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813033345/su2672Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536813033345/su2672Isup3.cml

Additional supporting information: crystallographic information; 3D view; checkCIF report

C15H10ClN3O2	F(000) = 616
Mr = 299.71	Dx = 1.550 Mg m−3
Orthorhombic, Pca21	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2c -2ac	Cell parameters from 3290 reflections
a = 31.0359 (12) Å	θ = 2.9–68.5°
b = 5.2549 (3) Å	µ = 2.72 mm−1
c = 7.8730 (4) Å	T = 102 K
V = 1284.01 (11) Å3	Plate, yellow
Z = 4	0.22 × 0.17 × 0.01 mm

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	1596 independent reflections
Radiation source: INCOATEC IµS micro–focus source	1434 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.109
Detector resolution: 10.4167 pixels mm-1	θmax = 68.5°, θmin = 5.7°
ω scans	h = −32→37
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −5→5
Tmin = 0.75, Tmax = 0.97	l = −8→9
4190 measured reflections

Refinement on F2	Secondary atom site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.059	W = 1/[Σ2(Fo2) + (0.0459P)2 + 3.7436P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.152	(Δ/σ)max < 0.001
S = 1.16	Δρmax = 0.30 e Å−3
1596 reflections	Δρmin = −0.37 e Å−3
193 parameters	Absolute structure: Flack (1983), 478 Friedal pairs (44% coverage)
3 restraints	Absolute structure parameter: −0.06 (5)
Primary atom site location: difference Fourier map

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
Cl1	−0.02432 (5)	0.0784 (4)	0.5130 (3)	0.0317 (6)
O1	0.15220 (15)	0.7554 (12)	0.7066 (7)	0.0247 (19)
O2	0.21783 (16)	0.0289 (11)	0.3951 (7)	0.0240 (19)
N1	0.18451 (17)	0.4151 (14)	0.5756 (8)	0.0187 (19)
N2	0.22478 (17)	0.5046 (12)	0.6135 (8)	0.0173 (19)
N3	0.29242 (19)	0.0513 (13)	0.4056 (8)	0.0203 (19)
C1	0.0263 (2)	0.2224 (17)	0.5393 (10)	0.026 (3)
C2	0.0616 (2)	0.1072 (16)	0.4604 (10)	0.023 (2)
C3	0.1021 (2)	0.2172 (17)	0.4862 (10)	0.026 (3)
C4	0.1069 (2)	0.4273 (16)	0.5882 (9)	0.020 (2)
C5	0.0705 (2)	0.5395 (17)	0.6625 (10)	0.026 (3)
C6	0.0301 (2)	0.4340 (18)	0.6391 (11)	0.028 (3)
C7	0.1495 (2)	0.5554 (18)	0.6291 (10)	0.024 (3)
C8	0.2560 (2)	0.3623 (15)	0.5494 (9)	0.018 (2)
C9	0.2517 (2)	0.1344 (16)	0.4425 (10)	0.022 (2)
C10	0.3234 (2)	0.2196 (15)	0.4808 (9)	0.018 (2)
C11	0.3677 (2)	0.2028 (16)	0.4744 (10)	0.022 (2)
C12	0.3910 (2)	0.3895 (16)	0.5590 (10)	0.025 (3)
C13	0.3700 (2)	0.5837 (17)	0.6480 (10)	0.025 (3)
C14	0.3253 (2)	0.5978 (15)	0.6566 (9)	0.019 (3)
C15	0.3018 (2)	0.4074 (16)	0.5723 (9)	0.021 (3)
H1	0.1866 (10)	0.264 (9)	0.523 (10)	0.0220*
H2	0.05820	−0.04030	0.39190	0.0280*
H3	0.12660	0.14550	0.43240	0.0310*
H3A	0.30090	−0.06130	0.32440	0.0250*
H5	0.07370	0.68880	0.72940	0.0320*
H6	0.00550	0.50730	0.69140	0.0340*
H11	0.38160	0.06920	0.41470	0.0270*
H12	0.42160	0.38530	0.55640	0.0290*
H13	0.38670	0.70950	0.70410	0.0300*
H14	0.31130	0.73060	0.71710	0.0230*

	U11	U22	U33	U12	U13	U23
Cl1	0.0189 (8)	0.0414 (13)	0.0349 (11)	−0.0052 (7)	−0.0031 (9)	0.0024 (11)
O1	0.022 (3)	0.030 (4)	0.022 (3)	0.004 (2)	−0.001 (2)	−0.009 (3)
O2	0.023 (3)	0.030 (4)	0.019 (3)	−0.002 (2)	−0.001 (2)	−0.007 (3)
N1	0.015 (3)	0.024 (4)	0.017 (3)	0.003 (2)	−0.002 (2)	−0.006 (3)
N2	0.019 (3)	0.021 (4)	0.012 (3)	0.000 (2)	0.002 (2)	0.000 (3)
N3	0.020 (3)	0.024 (4)	0.017 (3)	0.001 (3)	−0.001 (3)	−0.007 (3)
C1	0.020 (3)	0.040 (6)	0.019 (4)	−0.006 (3)	−0.008 (3)	0.009 (4)
C2	0.023 (3)	0.023 (5)	0.024 (4)	−0.003 (3)	−0.004 (3)	−0.006 (4)
C3	0.026 (4)	0.033 (5)	0.019 (4)	−0.001 (3)	−0.002 (4)	−0.005 (4)
C4	0.025 (4)	0.025 (5)	0.010 (3)	−0.004 (3)	−0.003 (3)	0.002 (3)
C5	0.022 (4)	0.039 (6)	0.018 (4)	0.003 (3)	0.001 (3)	−0.005 (4)
C6	0.021 (4)	0.040 (6)	0.023 (4)	0.007 (3)	0.005 (3)	−0.001 (4)
C7	0.022 (4)	0.036 (6)	0.015 (4)	0.006 (3)	0.001 (3)	0.003 (4)
C8	0.025 (3)	0.019 (5)	0.009 (4)	0.002 (3)	0.005 (3)	0.002 (3)
C9	0.013 (3)	0.038 (5)	0.016 (4)	0.001 (3)	−0.002 (3)	0.005 (4)
C10	0.017 (3)	0.025 (5)	0.013 (4)	0.000 (3)	−0.003 (3)	−0.004 (3)
C11	0.025 (3)	0.022 (5)	0.020 (4)	0.006 (3)	0.000 (3)	0.004 (4)
C12	0.017 (3)	0.034 (6)	0.023 (5)	0.002 (3)	0.000 (3)	0.003 (4)
C13	0.022 (4)	0.034 (6)	0.018 (4)	−0.001 (3)	−0.001 (3)	0.001 (4)
C14	0.026 (4)	0.016 (5)	0.016 (4)	0.000 (3)	−0.001 (3)	0.001 (3)
C15	0.024 (4)	0.022 (5)	0.018 (4)	0.002 (3)	−0.001 (3)	−0.001 (3)

Cl1—C1	1.756 (7)	C8—C9	1.470 (11)
O1—C7	1.218 (11)	C8—C15	1.452 (9)
O2—C9	1.246 (9)	C10—C15	1.394 (11)
N1—N2	1.368 (8)	C10—C11	1.379 (9)
N1—C7	1.379 (10)	C11—C12	1.389 (11)
N2—C8	1.324 (9)	C12—C13	1.399 (11)
N3—C9	1.368 (9)	C13—C14	1.391 (9)
N3—C10	1.434 (9)	C14—C15	1.405 (11)
N1—H1	0.90 (5)	C2—H2	0.9500
N3—H3A	0.9100	C3—H3	0.9500
C1—C6	1.367 (13)	C5—H5	0.9500
C1—C2	1.397 (10)	C6—H6	0.9500
C2—C3	1.398 (10)	C11—H11	0.9500
C3—C4	1.373 (12)	C12—H12	0.9500
C4—C5	1.402 (10)	C13—H13	0.9500
C4—C7	1.518 (10)	C14—H14	0.9500
C5—C6	1.383 (10)
N2—N1—C7	118.0 (7)	N3—C10—C15	109.1 (6)
N1—N2—C8	113.0 (6)	C11—C10—C15	123.0 (7)
C9—N3—C10	109.6 (6)	N3—C10—C11	127.9 (7)
C7—N1—H1	132 (2)	C10—C11—C12	117.2 (7)
N2—N1—H1	110 (2)	C11—C12—C13	120.9 (6)
C9—N3—H3A	129.00	C12—C13—C14	121.9 (7)
C10—N3—H3A	120.00	C13—C14—C15	117.2 (7)
Cl1—C1—C6	119.7 (5)	C8—C15—C14	133.1 (7)
C2—C1—C6	122.7 (6)	C10—C15—C14	119.9 (6)
Cl1—C1—C2	117.5 (6)	C8—C15—C10	106.9 (6)
C1—C2—C3	117.5 (7)	C1—C2—H2	121.00
C2—C3—C4	121.0 (7)	C3—C2—H2	121.00
C3—C4—C5	119.6 (6)	C2—C3—H3	119.00
C3—C4—C7	125.1 (6)	C4—C3—H3	120.00
C5—C4—C7	115.3 (7)	C4—C5—H5	120.00
C4—C5—C6	120.4 (8)	C6—C5—H5	120.00
C1—C6—C5	118.7 (7)	C1—C6—H6	121.00
O1—C7—C4	123.3 (6)	C5—C6—H6	121.00
N1—C7—C4	112.6 (7)	C10—C11—H11	121.00
O1—C7—N1	124.1 (6)	C12—C11—H11	122.00
N2—C8—C9	127.7 (6)	C11—C12—H12	120.00
N2—C8—C15	125.2 (7)	C13—C12—H12	120.00
C9—C8—C15	107.0 (6)	C12—C13—H13	119.00
N3—C9—C8	107.3 (6)	C14—C13—H13	119.00
O2—C9—N3	125.0 (7)	C13—C14—H14	121.00
O2—C9—C8	127.7 (6)	C15—C14—H14	122.00
C7—N1—N2—C8	−177.0 (7)	C5—C4—C7—N1	170.3 (7)
N2—N1—C7—O1	0.7 (12)	C4—C5—C6—C1	−1.5 (13)
N2—N1—C7—C4	−176.6 (6)	N2—C8—C9—O2	−1.7 (14)
N1—N2—C8—C9	2.1 (11)	N2—C8—C9—N3	179.7 (7)
N1—N2—C8—C15	−178.5 (7)	C15—C8—C9—O2	178.8 (8)
C10—N3—C9—O2	179.9 (7)	C15—C8—C9—N3	0.1 (8)
C10—N3—C9—C8	−1.4 (8)	N2—C8—C15—C10	−178.3 (7)
C9—N3—C10—C11	179.7 (8)	N2—C8—C15—C14	−1.6 (14)
C9—N3—C10—C15	2.2 (9)	C9—C8—C15—C10	1.2 (8)
Cl1—C1—C2—C3	−177.9 (6)	C9—C8—C15—C14	177.9 (8)
C6—C1—C2—C3	−0.2 (12)	N3—C10—C11—C12	−179.6 (7)
Cl1—C1—C6—C5	177.9 (7)	C15—C10—C11—C12	−2.4 (12)
C2—C1—C6—C5	0.3 (13)	N3—C10—C15—C8	−2.1 (8)
C1—C2—C3—C4	1.3 (12)	N3—C10—C15—C14	−179.3 (7)
C2—C3—C4—C5	−2.5 (12)	C11—C10—C15—C8	−179.7 (7)
C2—C3—C4—C7	177.8 (8)	C11—C10—C15—C14	3.1 (12)
C3—C4—C5—C6	2.6 (12)	C10—C11—C12—C13	0.7 (12)
C7—C4—C5—C6	−177.7 (8)	C11—C12—C13—C14	0.4 (12)
C3—C4—C7—O1	172.7 (8)	C12—C13—C14—C15	0.2 (12)
C3—C4—C7—N1	−10.0 (11)	C13—C14—C15—C8	−178.2 (8)
C5—C4—C7—O1	−7.0 (12)	C13—C14—C15—C10	−1.9 (11)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.90 (5)	1.87 (6)	2.685 (9)	151 (4)
N3—H3A···O1i	0.91	1.98	2.798 (8)	149
C11—H11···O1i	0.95	2.55	3.218 (10)	128
C14—H14···O2ii	0.95	2.29	3.233 (9)	172

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2	0.90 (5)	1.87 (6)	2.685 (9)	151 (4)
N3—H3A⋯O1i	0.91	1.98	2.798 (8)	149
C11—H11⋯O1i	0.95	2.55	3.218 (10)	128
C14—H14⋯O2ii	0.95	2.29	3.233 (9)	172

Symmetry codes: (i) ; (ii) .