5-Chloro-N'-cyclo-hexyl-idene-3-methyl-1H-indole-2-carbohydrazide.

In the title compound, C16H18ClN3O, the cyclo-hexane ring adopts a distorted chair conformation. In the crystal, pairs of mol-ecules are linked by N-H⋯O hydrogen bonds into inversion dimers, forming R 2 (2)(10) ring motifs. These dimers are connected through C-H⋯N hydrogen bonds into chains along the a axis, forming layers parallel to (101).

Related literature

For the design, synthesis and characterization of some bioactive indole derivatives, see: Akkurt et al. (2009 ▶, 2010 ▶); Cihan-Üstündağ & Çapan (2012 ▶); Güzel et al. (2006 ▶); Kaynak et al. (2005 ▶). For puckering analysis, see: Cremer & Pople (1975 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C16H18ClN3O

M = 303.78

Triclinic,

a = 5.2727 (5) Å

b = 9.7977 (9) Å

c = 15.2380 (15) Å

α = 102.229 (7)°

β = 95.732 (8)°

γ = 92.332 (7)°

V = 763.94 (13) Å3

Z = 2

Mo Kα radiation

μ = 0.25 mm−1

T = 296 K

0.76 × 0.36 × 0.02 mm

Data collection

Stoe IPDS 2 diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.831, T max = 0.995

7177 measured reflections

2929 independent reflections

1684 reflections with I > 2σ(I)

R int = 0.065

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.129

S = 1.01

2929 reflections

195 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.15 e Å−3

Δρmin = −0.16 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); 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: WinGX (Farrugia, 2012 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813016899/sj5335sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813016899/sj5335Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813016899/sj5335Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C16H18ClN3O	Z = 2
Mr = 303.78	F(000) = 320
Triclinic, P1	Dx = 1.321 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.2727 (5) Å	Cell parameters from 9705 reflections
b = 9.7977 (9) Å	θ = 2.1–28.0°
c = 15.2380 (15) Å	µ = 0.25 mm−1
α = 102.229 (7)°	T = 296 K
β = 95.732 (8)°	Plate, colourless
γ = 92.332 (7)°	0.76 × 0.36 × 0.02 mm
V = 763.94 (13) Å3

Stoe IPDS 2 diffractometer	2929 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	1684 reflections with I > 2σ(I)
Plane graphite monochromator	Rint = 0.065
Detector resolution: 6.67 pixels mm-1	θmax = 26.0°, θmin = 2.1°
ω scans	h = −6→6
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −12→12
Tmin = 0.831, Tmax = 0.995	l = −18→18
7177 measured reflections

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.129	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0554P)2] where P = (Fo2 + 2Fc2)/3
2929 reflections	(Δ/σ)max < 0.001
195 parameters	Δρmax = 0.15 e Å−3
0 restraints	Δρmin = −0.16 e Å−3

Experimental. UV (EtOH) λmax(nm)(ε) = 210.2 (11298); 230.6 (15341); 303.4 (14665). IR(KBr)ν = 3278 (N—H); 1639 (C=O);1624, 1537, 1514, 1471 (C=N, C=C) cm-1. 1H-NMR (500 MHz) (DMSO-d6 / TMS) d =1.56–1.72 (6H, m, CH2-cyc.*), 2.32 (2H, t, J=6.8 Hz, CH2-cyc.) 2.42–2.48 (5H, m, CH2-cyc. and 3-CH3-ind.*), 7.20 (1H, dd, J=8.7, 1.9 Hz, H6-ind.), 7.41 (1H, d, J=8.7 Hz, H7-ind.), 7.66 (1H, d, J=1.9 Hz, H4-ind.), 10.30 (1H, s, CONH), 11.50 (1H, s, NH-ind.) p.p.m.. MS (ESI–) m/z (%) = 302 ([M—H]-, 100). Analysis calculated for C16H18ClN3O: C 63.26, H 5.97, N 13.83%. Found: C 63.12, H 5.97, N 13.86%.(*cyc. = cyclohexylidene, ind. = indole).

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	0.5891 (2)	0.46594 (11)	0.20802 (7)	0.1086 (4)
O1	0.1519 (4)	0.0786 (2)	0.61618 (12)	0.0717 (7)
N1	0.2262 (4)	0.1409 (2)	0.45351 (13)	0.0589 (8)
N2	0.5585 (5)	0.1489 (3)	0.67430 (15)	0.0597 (8)
N3	0.5305 (4)	0.1037 (2)	0.75354 (15)	0.0628 (8)
C1	0.2826 (5)	0.2059 (3)	0.38687 (17)	0.0538 (8)
C2	0.1513 (6)	0.1988 (3)	0.30110 (18)	0.0654 (10)
C3	0.2502 (6)	0.2795 (3)	0.24870 (19)	0.0705 (11)
C4	0.4744 (6)	0.3636 (3)	0.27889 (19)	0.0691 (11)
C5	0.6043 (5)	0.3719 (3)	0.3623 (2)	0.0648 (10)
C6	0.5060 (4)	0.2920 (3)	0.41855 (17)	0.0508 (8)
C7	0.5838 (4)	0.2775 (3)	0.50912 (16)	0.0512 (8)
C8	0.4070 (5)	0.1827 (3)	0.52722 (16)	0.0511 (8)
C9	0.8061 (5)	0.3606 (3)	0.5689 (2)	0.0686 (10)
C10	0.3624 (5)	0.1311 (3)	0.60883 (17)	0.0543 (9)
C11	0.7122 (5)	0.1360 (3)	0.81721 (18)	0.0597 (9)
C12	0.9530 (6)	0.2231 (4)	0.8204 (2)	0.0866 (13)
C13	1.0168 (7)	0.3247 (4)	0.9086 (2)	0.0993 (16)
C14	1.0052 (7)	0.2603 (4)	0.9900 (2)	0.0876 (13)
C15	0.7463 (6)	0.1875 (4)	0.9862 (2)	0.0837 (13)
C16	0.6818 (6)	0.0800 (4)	0.9003 (2)	0.0820 (11)
H1	0.09730	0.08260	0.45020	0.0710*
H2	0.00300	0.14140	0.28090	0.0790*
H2A	0.701 (5)	0.174 (3)	0.6650 (17)	0.054 (8)*
H3	0.16670	0.27840	0.19180	0.0850*
H5	0.75350	0.42900	0.38110	0.0780*
H9A	0.85040	0.44140	0.54590	0.1030*
H9B	0.94970	0.30360	0.56980	0.1030*
H9C	0.76010	0.39010	0.62910	0.1030*
H12A	0.93570	0.27410	0.77230	0.1040*
H12B	1.09240	0.16220	0.80990	0.1040*
H13A	0.89910	0.39870	0.91220	0.1190*
H13B	1.18740	0.36690	0.91050	0.1190*
H14A	1.13590	0.19360	0.99100	0.1050*
H14B	1.03740	0.33270	1.04480	0.1050*
H15A	0.74350	0.14270	1.03710	0.1010*
H15B	0.61810	0.25620	0.99110	0.1010*
H16A	0.50660	0.04370	0.89750	0.0980*
H16B	0.79110	0.00290	0.90090	0.0980*

	U11	U22	U33	U12	U13	U23
Cl1	0.1362 (8)	0.1232 (8)	0.0844 (7)	−0.0039 (6)	0.0217 (6)	0.0607 (6)
O1	0.0767 (12)	0.0851 (14)	0.0498 (11)	−0.0264 (11)	−0.0034 (9)	0.0179 (10)
N1	0.0662 (13)	0.0625 (14)	0.0445 (12)	−0.0171 (11)	−0.0010 (10)	0.0109 (10)
N2	0.0590 (13)	0.0774 (16)	0.0448 (13)	−0.0043 (12)	0.0028 (11)	0.0210 (11)
N3	0.0722 (14)	0.0709 (15)	0.0491 (13)	−0.0018 (12)	0.0054 (12)	0.0236 (12)
C1	0.0654 (15)	0.0521 (15)	0.0427 (14)	0.0010 (13)	0.0064 (12)	0.0080 (12)
C2	0.0775 (17)	0.0694 (18)	0.0455 (15)	−0.0025 (15)	−0.0039 (14)	0.0102 (13)
C3	0.090 (2)	0.077 (2)	0.0444 (15)	0.0084 (17)	0.0005 (15)	0.0155 (14)
C4	0.0879 (19)	0.0721 (19)	0.0551 (18)	0.0077 (16)	0.0153 (16)	0.0274 (15)
C5	0.0675 (16)	0.0657 (17)	0.0633 (18)	−0.0028 (14)	0.0096 (14)	0.0193 (14)
C6	0.0536 (13)	0.0520 (15)	0.0471 (14)	0.0049 (12)	0.0050 (11)	0.0116 (12)
C7	0.0511 (13)	0.0536 (15)	0.0463 (14)	0.0012 (12)	0.0006 (11)	0.0079 (12)
C8	0.0570 (14)	0.0540 (15)	0.0407 (14)	0.0021 (13)	0.0014 (11)	0.0086 (12)
C9	0.0648 (16)	0.078 (2)	0.0613 (17)	−0.0071 (15)	−0.0059 (14)	0.0197 (15)
C10	0.0659 (16)	0.0502 (15)	0.0431 (14)	−0.0023 (13)	0.0016 (13)	0.0054 (12)
C11	0.0635 (15)	0.0719 (18)	0.0463 (15)	0.0060 (14)	0.0073 (13)	0.0177 (13)
C12	0.0652 (17)	0.143 (3)	0.0556 (18)	−0.0114 (19)	0.0048 (14)	0.0348 (19)
C13	0.112 (3)	0.122 (3)	0.065 (2)	−0.040 (2)	−0.0189 (19)	0.045 (2)
C14	0.099 (2)	0.112 (3)	0.0530 (18)	−0.013 (2)	−0.0066 (17)	0.0313 (18)
C15	0.092 (2)	0.116 (3)	0.0491 (17)	0.000 (2)	0.0086 (16)	0.0325 (18)
C16	0.097 (2)	0.092 (2)	0.0633 (19)	−0.0084 (19)	−0.0014 (17)	0.0386 (18)

Cl1—C4	1.754 (3)	C12—C13	1.492 (5)
O1—C10	1.230 (3)	C13—C14	1.511 (5)
N1—C1	1.358 (3)	C14—C15	1.504 (5)
N1—C8	1.378 (3)	C15—C16	1.495 (5)
N2—N3	1.390 (3)	C2—H2	0.9300
N2—C10	1.342 (4)	C3—H3	0.9300
N3—C11	1.272 (3)	C5—H5	0.9300
N1—H1	0.8600	C9—H9A	0.9600
N2—H2A	0.82 (3)	C9—H9B	0.9600
C1—C2	1.403 (4)	C9—H9C	0.9600
C1—C6	1.402 (4)	C12—H12A	0.9700
C2—C3	1.361 (4)	C12—H12B	0.9700
C3—C4	1.393 (4)	C13—H13A	0.9700
C4—C5	1.367 (4)	C13—H13B	0.9700
C5—C6	1.399 (4)	C14—H14A	0.9700
C6—C7	1.438 (4)	C14—H14B	0.9700
C7—C9	1.504 (4)	C15—H15A	0.9700
C7—C8	1.377 (4)	C15—H15B	0.9700
C8—C10	1.474 (4)	C16—H16A	0.9700
C11—C16	1.503 (4)	C16—H16B	0.9700
C11—C12	1.492 (4)
C1—N1—C8	109.6 (2)	C3—C2—H2	121.00
N3—N2—C10	120.0 (2)	C2—C3—H3	119.00
N2—N3—C11	117.5 (2)	C4—C3—H3	120.00
C8—N1—H1	125.00	C4—C5—H5	121.00
C1—N1—H1	125.00	C6—C5—H5	121.00
N3—N2—H2A	118.7 (18)	C7—C9—H9A	109.00
C10—N2—H2A	120.5 (18)	C7—C9—H9B	109.00
N1—C1—C6	107.7 (2)	C7—C9—H9C	109.00
C2—C1—C6	122.3 (3)	H9A—C9—H9B	109.00
N1—C1—C2	130.0 (3)	H9A—C9—H9C	109.00
C1—C2—C3	117.2 (3)	H9B—C9—H9C	110.00
C2—C3—C4	121.1 (3)	C11—C12—H12A	109.00
Cl1—C4—C3	118.5 (2)	C11—C12—H12B	109.00
Cl1—C4—C5	119.0 (2)	C13—C12—H12A	109.00
C3—C4—C5	122.5 (3)	C13—C12—H12B	109.00
C4—C5—C6	118.0 (3)	H12A—C12—H12B	108.00
C1—C6—C5	119.0 (2)	C12—C13—H13A	109.00
C5—C6—C7	133.4 (2)	C12—C13—H13B	109.00
C1—C6—C7	107.6 (2)	C14—C13—H13A	109.00
C6—C7—C8	105.7 (2)	C14—C13—H13B	109.00
C6—C7—C9	123.9 (2)	H13A—C13—H13B	108.00
C8—C7—C9	130.3 (2)	C13—C14—H14A	110.00
C7—C8—C10	133.6 (2)	C13—C14—H14B	110.00
N1—C8—C7	109.5 (2)	C15—C14—H14A	110.00
N1—C8—C10	116.6 (2)	C15—C14—H14B	110.00
O1—C10—C8	120.5 (2)	H14A—C14—H14B	108.00
N2—C10—C8	116.7 (2)	C14—C15—H15A	109.00
O1—C10—N2	122.8 (3)	C14—C15—H15B	109.00
N3—C11—C12	128.4 (3)	C16—C15—H15A	109.00
N3—C11—C16	116.3 (3)	C16—C15—H15B	109.00
C12—C11—C16	115.3 (2)	H15A—C15—H15B	108.00
C11—C12—C13	112.6 (3)	C11—C16—H16A	109.00
C12—C13—C14	113.9 (3)	C11—C16—H16B	109.00
C13—C14—C15	109.9 (3)	C15—C16—H16A	109.00
C14—C15—C16	111.7 (3)	C15—C16—H16B	109.00
C11—C16—C15	113.3 (3)	H16A—C16—H16B	108.00
C1—C2—H2	121.00
C1—N1—C8—C10	174.9 (2)	C4—C5—C6—C7	−177.9 (3)
C8—N1—C1—C2	−178.3 (3)	C5—C6—C7—C9	3.2 (5)
C8—N1—C1—C6	0.0 (3)	C5—C6—C7—C8	179.7 (3)
C1—N1—C8—C7	0.5 (3)	C1—C6—C7—C8	0.8 (3)
N3—N2—C10—C8	179.6 (2)	C1—C6—C7—C9	−175.7 (2)
N3—N2—C10—O1	1.8 (4)	C6—C7—C8—C10	−173.9 (3)
C10—N2—N3—C11	−172.8 (3)	C9—C7—C8—C10	2.3 (5)
N2—N3—C11—C16	−177.2 (3)	C9—C7—C8—N1	175.4 (3)
N2—N3—C11—C12	2.9 (4)	C6—C7—C8—N1	−0.8 (3)
N1—C1—C6—C7	−0.5 (3)	N1—C8—C10—N2	167.7 (3)
C6—C1—C2—C3	0.2 (4)	C7—C8—C10—O1	158.3 (3)
N1—C1—C6—C5	−179.6 (2)	C7—C8—C10—N2	−19.5 (5)
C2—C1—C6—C7	178.0 (3)	N1—C8—C10—O1	−14.4 (4)
C2—C1—C6—C5	−1.1 (4)	N3—C11—C12—C13	136.1 (3)
N1—C1—C2—C3	178.2 (3)	C16—C11—C12—C13	−43.7 (4)
C1—C2—C3—C4	1.0 (4)	N3—C11—C16—C15	−134.0 (3)
C2—C3—C4—Cl1	−179.5 (2)	C12—C11—C16—C15	45.9 (4)
C2—C3—C4—C5	−1.1 (5)	C11—C12—C13—C14	49.1 (4)
C3—C4—C5—C6	0.1 (4)	C12—C13—C14—C15	−55.6 (4)
Cl1—C4—C5—C6	178.5 (2)	C13—C14—C15—C16	56.2 (4)
C4—C5—C6—C1	1.0 (4)	C14—C15—C16—C11	−52.0 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.86	2.03	2.826 (3)	153
C12—H12A···N2	0.97	2.47	2.842 (4)	102
C12—H12B···N3ii	0.97	2.59	3.476 (4)	152

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.86	2.03	2.826 (3)	153
C12—H12B⋯N3ii	0.97	2.59	3.476 (4)	152

Symmetry codes: (i) ; (ii) .