3-(4-Chloro­but­yl)-3H-indole-5-carbo­nitrile. Corrigendum

Manikandan, D.; Gomathi, S.; Nirmalram, J.S.; Tagore, S.S.; Sethuraman, V.; Agim, J.; Butcher, R.

doi:10.1107/S2414314617011324

addenda and errata

IUCrDATA

ISSN: 2414-3146

Volume 2| Part 9| September 2017| x171132

https://doi.org/10.1107/S2414314617011324

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3-(4-Chlorobutyl)-3H-indole-5-carbonitrile. Corrigendum

Devakumar Manikandan,^a Sundaramoorthy Gomathi,^a Jeyaraman Selvaraj Nirmalram,^b Sadasivam Sharmila Tagore,^a Velusamy Sethuraman,^a ^* Joseph Agim ^c and Ray Butcher ^c

^aDepartment of Chemistry, Periyar Maniammai University, Thanjavur 613 403, Tamil Nadu, India, ^bCentre for Research and Development, PRIST University, Thanjavur 613 403, Tamil Nadu, India, and ^cInorganic & Structural Chemistry, Howard University, Washington, DC 20059, USA
^*Correspondence e-mail: [email protected]

Edited by P. C. Healy, Griffith University, Australia (Received 24 July 2017; accepted 1 August 2017; online 29 September 2017)

In the paper by Manikandan et al. [IUCrData (2017). 2, x170376], a proton on the indole N was missed in the structure solution. The proton is now added and the changes are reported here. The title, scheme, Figs. 1 and 2, the hydrogen-bonding table, the crystallographic data table and description of the supramolecular architectures are corrected.

Figure 1
The asymmetric unit of (I), shown with 50% probability displacement ellipsoids.

Figure 2
A view of two-dimensional supramolecular sheet via N—H⋯N and weak intermolecular C—H⋯Cl hydrogen bonding, aromatic π–π and weak C—H⋯π interactions. [Symmetry codes: (i) 1 − x, − $[{1\over 2}]$ + y, $[{1\over 2}]$ − z; (ii) −x, 1 − y, 1 − z; (iii) 1 − x, 1 − y, 1 − z; (iv) x, $[{3\over 2}]$ − y, − $[{1\over 2}]$ + z; (v) x, 1 + y, z.]

CCDC references: 1573008-1573009; 1573008; 1573009

Structure description

In the paper by Manikandan et al. (2017 ), a proton on the indole N atom was missed in the structure solution. The proton has been added and the changes are reported here. The title and the chemical name of the compound should be `3-(4-Chlorobutyl)-1H-indole-5-carbonitrile'.

The proton on the indole nitrogen (N1) is involved in an N—H⋯N hydrogen bond with symmetry-related neighboring molecules and forms an R₃³(23) ring motif instead of a chain with a C(9) graph set.

The figure caption of Fig. 2, the hydrogen-bonding table and the crystallographic data table are updated. In the structure description section, the sentence `In the crystal, neighboring molecules self-assemble through weak C—H⋯Cl interactions (Table 1), forming zigzag supramolecular C(9) chains extending along the b-axis direction, as shown in Fig. 2a.' should be replaced by `In the crystal, neighboring molecules self-assemble through N—H⋯N and weak C—H⋯Cl interactions (Table 1), resulting in an R₃³(23) ring motif, which forms a supramolecular sheet extending along the b axis, as shown in Fig. 2a.' Revised experimental details are given in Table 2.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N2ⁱ	0.787 (19)	2.263 (19)	3.039 (2)	168.7 (19)
C4—H4⋯Cl1ⁱⁱ	0.95	2.80	3.7497 (18)	178
Symmetry codes: (i) x, y+1, z; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Table 2
Updated experimental details

Crystal data
Chemical formula	C₁₃H₁₃ClN₂
M_r	232.70

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.097, 1.05
No. of parameters	149
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.24

Supporting information

CCDC references: 1573008-1573009; 1573008; 1573009

Crystal structure: contains datablocks global, shelx. DOI: https://doi.org/10.1107/S2414314617011324/hg9020sup1.cif

Structure factors: contains datablock shelx. DOI: https://doi.org/10.1107/S2414314617011324/hg9020sup1.hkl

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXL97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009), Mercury (Macrae et al., 2008) and POVRay (Cason, 2004); software used to prepare material for publication: PLATON (Spek, 2009) and publCIF (Westrip, 2010).

3-(4-Chlorobutyl)-1H-indole-5-carbonitrile top

Crystal data top

C₁₃H₁₃ClN₂	F(000) = 488
M_r = 232.70	D_x = 1.317 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1952 reflections
a = 8.870 (2) Å	θ = 2.6–24.6°
b = 9.271 (2) Å	µ = 0.30 mm⁻¹
c = 14.498 (3) Å	T = 100 K
β = 100.236 (4)°	Block, colourless
V = 1173.3 (4) Å³	0.18 × 0.17 × 0.15 mm
Z = 4

Data collection top

Bruker APEXII diffractometer	1632 reflections with I > 2σ(I)
Detector resolution: 18.4 pixels mm^-1	R_int = 0.039
ω scans	θ_max = 24.6°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008)	h = −10→10
T_min = 0.618, T_max = 0.745	k = −10→10
7342 measured reflections	l = −17→16
1952 independent reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.097	w = 1/[Σ²(FO²) + (0.0615P)² + 0.1055P] where P = (FO² + 2FC²)/3
S = 1.05	(Δ/σ)_max < 0.001
1952 reflections	Δρ_max = 0.29 e Å⁻³
149 parameters	Δρ_min = −0.24 e Å⁻³

Special details top

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 esds 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 > 2sigma(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	0.64036 (6)	0.62781 (5)	0.10556 (3)	0.0373 (2)
N1	0.17181 (16)	0.77684 (15)	0.56118 (10)	0.0202 (4)
N2	0.10999 (16)	0.07038 (15)	0.64000 (9)	0.0248 (5)
C2	0.24682 (17)	0.77009 (16)	0.48566 (10)	0.0193 (5)
C3	0.27344 (17)	0.62953 (17)	0.46452 (11)	0.0177 (5)
C4	0.19953 (17)	0.39623 (17)	0.54478 (10)	0.0160 (5)
C5	0.12918 (17)	0.34723 (16)	0.61736 (10)	0.0170 (5)
C6	0.07019 (17)	0.44431 (16)	0.67723 (10)	0.0180 (5)
C7	0.07908 (18)	0.59143 (17)	0.66461 (11)	0.0190 (5)
C8	0.14877 (17)	0.64002 (16)	0.59099 (11)	0.0175 (5)
C9	0.21099 (16)	0.54435 (17)	0.53130 (10)	0.0154 (4)
C10	0.11661 (17)	0.19387 (17)	0.63039 (11)	0.0187 (5)
C11	0.34895 (17)	0.56971 (18)	0.38827 (10)	0.0185 (5)
C12	0.40919 (18)	0.68138 (17)	0.32640 (11)	0.0200 (5)
C13	0.48445 (18)	0.60781 (16)	0.25127 (10)	0.0189 (5)
C14	0.54689 (19)	0.71647 (17)	0.19063 (11)	0.0212 (5)
H1	0.147 (2)	0.847 (2)	0.5852 (15)	0.033 (6)*
H2	0.27584	0.85143	0.45299	0.0230*
H4	0.23903	0.32991	0.50516	0.0190*
H6	0.02389	0.40786	0.72672	0.0220*
H7	0.03936	0.65728	0.70443	0.0230*
H11A	0.27441	0.50716	0.34779	0.0220*
H11B	0.43558	0.50800	0.41731	0.0220*
H12A	0.32349	0.74283	0.29573	0.0240*
H12B	0.48506	0.74413	0.36573	0.0240*
H13A	0.40795	0.54624	0.21146	0.0230*
H13B	0.56878	0.54494	0.28208	0.0230*
H14A	0.46214	0.77713	0.15787	0.0250*
H14B	0.62099	0.78019	0.23049	0.0250*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0598 (4)	0.0245 (3)	0.0364 (3)	0.0068 (2)	0.0329 (2)	0.0054 (2)
N1	0.0273 (8)	0.0099 (7)	0.0255 (7)	0.0006 (6)	0.0108 (6)	−0.0031 (6)
N2	0.0349 (8)	0.0165 (8)	0.0256 (8)	0.0013 (6)	0.0125 (6)	0.0011 (6)
C2	0.0227 (8)	0.0148 (8)	0.0217 (8)	−0.0020 (6)	0.0077 (7)	0.0029 (6)
C3	0.0163 (8)	0.0183 (9)	0.0191 (8)	−0.0002 (6)	0.0046 (6)	0.0012 (6)
C4	0.0172 (8)	0.0146 (8)	0.0169 (8)	0.0019 (6)	0.0049 (6)	−0.0018 (6)
C5	0.0191 (8)	0.0136 (8)	0.0182 (8)	0.0003 (6)	0.0032 (6)	−0.0002 (6)
C6	0.0198 (8)	0.0184 (8)	0.0178 (8)	−0.0011 (7)	0.0085 (6)	0.0012 (6)
C7	0.0221 (8)	0.0156 (8)	0.0210 (8)	0.0012 (7)	0.0082 (7)	−0.0029 (6)
C8	0.0177 (8)	0.0145 (9)	0.0202 (8)	0.0007 (6)	0.0035 (6)	−0.0008 (6)
C9	0.0150 (8)	0.0155 (8)	0.0161 (7)	0.0001 (6)	0.0040 (6)	−0.0002 (6)
C10	0.0203 (8)	0.0191 (9)	0.0184 (8)	0.0019 (7)	0.0079 (7)	0.0000 (7)
C11	0.0207 (9)	0.0166 (8)	0.0194 (8)	0.0004 (6)	0.0066 (7)	0.0020 (6)
C12	0.0224 (9)	0.0177 (8)	0.0211 (8)	0.0006 (7)	0.0072 (7)	0.0025 (7)
C13	0.0234 (9)	0.0159 (8)	0.0185 (8)	−0.0007 (7)	0.0066 (7)	0.0005 (6)
C14	0.0278 (9)	0.0171 (8)	0.0214 (8)	0.0007 (7)	0.0114 (7)	−0.0001 (7)

Geometric parameters (Å, º) top

Cl1—C14	1.8021 (17)	C11—C12	1.527 (2)
N1—C2	1.380 (2)	C12—C13	1.535 (2)
N1—C8	1.367 (2)	C13—C14	1.506 (2)
N2—C10	1.156 (2)	C2—H2	0.9500
N1—H1	0.787 (19)	C4—H4	0.9500
C2—C3	1.369 (2)	C6—H6	0.9500
C3—C9	1.435 (2)	C7—H7	0.9500
C3—C11	1.497 (2)	C11—H11A	0.9900
C4—C9	1.393 (2)	C11—H11B	0.9900
C4—C5	1.392 (2)	C12—H12A	0.9900
C5—C6	1.414 (2)	C12—H12B	0.9900
C5—C10	1.441 (2)	C13—H13A	0.9900
C6—C7	1.380 (2)	C13—H13B	0.9900
C7—C8	1.400 (2)	C14—H14A	0.9900
C8—C9	1.418 (2)	C14—H14B	0.9900

C2—N1—C8	109.21 (13)	C5—C4—H4	121.00
C8—N1—H1	123.9 (14)	C9—C4—H4	121.00
C2—N1—H1	126.9 (14)	C5—C6—H6	120.00
N1—C2—C3	110.34 (13)	C7—C6—H6	120.00
C2—C3—C11	129.47 (14)	C6—C7—H7	121.00
C2—C3—C9	105.68 (13)	C8—C7—H7	121.00
C9—C3—C11	124.85 (14)	C3—C11—H11A	108.00
C5—C4—C9	118.78 (14)	C3—C11—H11B	108.00
C4—C5—C6	121.40 (14)	C12—C11—H11A	108.00
C6—C5—C10	120.12 (13)	C12—C11—H11B	108.00
C4—C5—C10	118.47 (14)	H11A—C11—H11B	107.00
C5—C6—C7	120.77 (14)	C11—C12—H12A	109.00
C6—C7—C8	117.55 (14)	C11—C12—H12B	109.00
N1—C8—C7	130.61 (14)	C13—C12—H12A	109.00
N1—C8—C9	106.93 (13)	C13—C12—H12B	109.00
C7—C8—C9	122.46 (14)	H12A—C12—H12B	108.00
C3—C9—C4	133.13 (14)	C12—C13—H13A	109.00
C4—C9—C8	119.01 (13)	C12—C13—H13B	109.00
C3—C9—C8	107.84 (13)	C14—C13—H13A	109.00
N2—C10—C5	178.25 (17)	C14—C13—H13B	109.00
C3—C11—C12	115.58 (14)	H13A—C13—H13B	108.00
C11—C12—C13	110.93 (13)	Cl1—C14—H14A	109.00
C12—C13—C14	111.62 (13)	Cl1—C14—H14B	109.00
Cl1—C14—C13	110.86 (11)	C13—C14—H14A	109.00
N1—C2—H2	125.00	C13—C14—H14B	109.00
C3—C2—H2	125.00	H14A—C14—H14B	108.00

C8—N1—C2—C3	0.28 (18)	C5—C4—C9—C8	−0.9 (2)
C2—N1—C8—C7	179.69 (16)	C4—C5—C6—C7	0.8 (2)
C2—N1—C8—C9	−0.39 (17)	C10—C5—C6—C7	−178.90 (14)
N1—C2—C3—C9	−0.05 (18)	C5—C6—C7—C8	−0.2 (2)
N1—C2—C3—C11	179.18 (15)	C6—C7—C8—N1	179.00 (16)
C2—C3—C9—C4	178.35 (16)	C6—C7—C8—C9	−0.9 (2)
C2—C3—C9—C8	−0.19 (17)	N1—C8—C9—C3	0.35 (17)
C11—C3—C9—C4	−0.9 (3)	N1—C8—C9—C4	−178.43 (14)
C11—C3—C9—C8	−179.47 (14)	C7—C8—C9—C3	−179.72 (14)
C2—C3—C11—C12	1.8 (2)	C7—C8—C9—C4	1.5 (2)
C9—C3—C11—C12	−179.05 (14)	C3—C11—C12—C13	179.79 (13)
C9—C4—C5—C6	−0.2 (2)	C11—C12—C13—C14	−179.04 (13)
C9—C4—C5—C10	179.49 (14)	C12—C13—C14—Cl1	178.05 (11)
C5—C4—C9—C3	−179.31 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N2ⁱ	0.787 (19)	2.263 (19)	3.039 (2)	168.7 (19)
C4—H4···Cl1ⁱⁱ	0.95	2.80	3.7497 (18)	178

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

References

Manikandan, D., Gomathi, S., Nirmalram, J. S., Tagore, S. S., Sethuraman, V., Agim, J. & Butcher, R. J. (2017). IUCrData, 2, x170376. Google Scholar

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