addenda and errata\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoIUCrDATA
ISSN: 2414-3146

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

CROSSMARK_Color_square_no_text.svg

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: lvsethu13@gmail.com

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[link] and 2[link], the hydrogen-bonding table, the crystallographic data table and description of the supra­molecular architectures are corrected.

[Scheme 1]
[Scheme 3D1]
[Scheme 1-3D1]
[Figure 1]
Figure 1
The asymmetric unit of (I), shown with 50% probability displacement ellipsoids.
[Figure 2]
Figure 2
A view of two-dimensional supra­molecular sheet via N—H⋯N and weak inter­molecular C—H⋯Cl hydrogen bonding, aromatic ππ 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.]

Structure description

In the paper by Manikandan et al. (2017[Manikandan, D., Gomathi, S., Nirmalram, J. S., Tagore, S. S., Sethuraman, V., Agim, J. & Butcher, R. J. (2017). IUCrData, 2, x170376.]), 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[link], 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[link]), forming zigzag supra­molecular C(9) chains extending along the b-axis direction, as shown in Fig. 2[link]a.' should be replaced by `In the crystal, neighboring mol­ecules self-assemble through N—H⋯N and weak C—H⋯Cl inter­actions (Table 1[link]), resulting in an R33(23) ring motif, which forms a supra­molecular sheet extending along the b axis, as shown in Fig. 2[link]a.' Revised experimental details are given in Table 2[link].

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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
Mr 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
Δρmax, Δρmin (e Å−3) 0.29, −0.24

Supporting information


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
C13H13ClN2F(000) = 488
Mr = 232.70Dx = 1.317 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1952 reflections
a = 8.870 (2) Åθ = 2.6–24.6°
b = 9.271 (2) ŵ = 0.30 mm1
c = 14.498 (3) ÅT = 100 K
β = 100.236 (4)°Block, colourless
V = 1173.3 (4) Å30.18 × 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-1Rint = 0.039
ω scansθmax = 24.6°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2008)
h = 1010
Tmin = 0.618, Tmax = 0.745k = 1010
7342 measured reflectionsl = 1716
1952 independent reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.034H 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 reflectionsΔρmax = 0.29 e Å3
149 parametersΔρmin = 0.24 e Å3
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
xyzUiso*/Ueq
Cl10.64036 (6)0.62781 (5)0.10556 (3)0.0373 (2)
N10.17181 (16)0.77684 (15)0.56118 (10)0.0202 (4)
N20.10999 (16)0.07038 (15)0.64000 (9)0.0248 (5)
C20.24682 (17)0.77009 (16)0.48566 (10)0.0193 (5)
C30.27344 (17)0.62953 (17)0.46452 (11)0.0177 (5)
C40.19953 (17)0.39623 (17)0.54478 (10)0.0160 (5)
C50.12918 (17)0.34723 (16)0.61736 (10)0.0170 (5)
C60.07019 (17)0.44431 (16)0.67723 (10)0.0180 (5)
C70.07908 (18)0.59143 (17)0.66461 (11)0.0190 (5)
C80.14877 (17)0.64002 (16)0.59099 (11)0.0175 (5)
C90.21099 (16)0.54435 (17)0.53130 (10)0.0154 (4)
C100.11661 (17)0.19387 (17)0.63039 (11)0.0187 (5)
C110.34895 (17)0.56971 (18)0.38827 (10)0.0185 (5)
C120.40919 (18)0.68138 (17)0.32640 (11)0.0200 (5)
C130.48445 (18)0.60781 (16)0.25127 (10)0.0189 (5)
C140.54689 (19)0.71647 (17)0.19063 (11)0.0212 (5)
H10.147 (2)0.847 (2)0.5852 (15)0.033 (6)*
H20.275840.851430.452990.0230*
H40.239030.329910.505160.0190*
H60.023890.407860.726720.0220*
H70.039360.657280.704430.0230*
H11A0.274410.507160.347790.0220*
H11B0.435580.508000.417310.0220*
H12A0.323490.742830.295730.0240*
H12B0.485060.744130.365730.0240*
H13A0.407950.546240.211460.0230*
H13B0.568780.544940.282080.0230*
H14A0.462140.777130.157870.0250*
H14B0.620990.780190.230490.0250*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0598 (4)0.0245 (3)0.0364 (3)0.0068 (2)0.0329 (2)0.0054 (2)
N10.0273 (8)0.0099 (7)0.0255 (7)0.0006 (6)0.0108 (6)0.0031 (6)
N20.0349 (8)0.0165 (8)0.0256 (8)0.0013 (6)0.0125 (6)0.0011 (6)
C20.0227 (8)0.0148 (8)0.0217 (8)0.0020 (6)0.0077 (7)0.0029 (6)
C30.0163 (8)0.0183 (9)0.0191 (8)0.0002 (6)0.0046 (6)0.0012 (6)
C40.0172 (8)0.0146 (8)0.0169 (8)0.0019 (6)0.0049 (6)0.0018 (6)
C50.0191 (8)0.0136 (8)0.0182 (8)0.0003 (6)0.0032 (6)0.0002 (6)
C60.0198 (8)0.0184 (8)0.0178 (8)0.0011 (7)0.0085 (6)0.0012 (6)
C70.0221 (8)0.0156 (8)0.0210 (8)0.0012 (7)0.0082 (7)0.0029 (6)
C80.0177 (8)0.0145 (9)0.0202 (8)0.0007 (6)0.0035 (6)0.0008 (6)
C90.0150 (8)0.0155 (8)0.0161 (7)0.0001 (6)0.0040 (6)0.0002 (6)
C100.0203 (8)0.0191 (9)0.0184 (8)0.0019 (7)0.0079 (7)0.0000 (7)
C110.0207 (9)0.0166 (8)0.0194 (8)0.0004 (6)0.0066 (7)0.0020 (6)
C120.0224 (9)0.0177 (8)0.0211 (8)0.0006 (7)0.0072 (7)0.0025 (7)
C130.0234 (9)0.0159 (8)0.0185 (8)0.0007 (7)0.0066 (7)0.0005 (6)
C140.0278 (9)0.0171 (8)0.0214 (8)0.0007 (7)0.0114 (7)0.0001 (7)
Geometric parameters (Å, º) top
Cl1—C141.8021 (17)C11—C121.527 (2)
N1—C21.380 (2)C12—C131.535 (2)
N1—C81.367 (2)C13—C141.506 (2)
N2—C101.156 (2)C2—H20.9500
N1—H10.787 (19)C4—H40.9500
C2—C31.369 (2)C6—H60.9500
C3—C91.435 (2)C7—H70.9500
C3—C111.497 (2)C11—H11A0.9900
C4—C91.393 (2)C11—H11B0.9900
C4—C51.392 (2)C12—H12A0.9900
C5—C61.414 (2)C12—H12B0.9900
C5—C101.441 (2)C13—H13A0.9900
C6—C71.380 (2)C13—H13B0.9900
C7—C81.400 (2)C14—H14A0.9900
C8—C91.418 (2)C14—H14B0.9900
C2—N1—C8109.21 (13)C5—C4—H4121.00
C8—N1—H1123.9 (14)C9—C4—H4121.00
C2—N1—H1126.9 (14)C5—C6—H6120.00
N1—C2—C3110.34 (13)C7—C6—H6120.00
C2—C3—C11129.47 (14)C6—C7—H7121.00
C2—C3—C9105.68 (13)C8—C7—H7121.00
C9—C3—C11124.85 (14)C3—C11—H11A108.00
C5—C4—C9118.78 (14)C3—C11—H11B108.00
C4—C5—C6121.40 (14)C12—C11—H11A108.00
C6—C5—C10120.12 (13)C12—C11—H11B108.00
C4—C5—C10118.47 (14)H11A—C11—H11B107.00
C5—C6—C7120.77 (14)C11—C12—H12A109.00
C6—C7—C8117.55 (14)C11—C12—H12B109.00
N1—C8—C7130.61 (14)C13—C12—H12A109.00
N1—C8—C9106.93 (13)C13—C12—H12B109.00
C7—C8—C9122.46 (14)H12A—C12—H12B108.00
C3—C9—C4133.13 (14)C12—C13—H13A109.00
C4—C9—C8119.01 (13)C12—C13—H13B109.00
C3—C9—C8107.84 (13)C14—C13—H13A109.00
N2—C10—C5178.25 (17)C14—C13—H13B109.00
C3—C11—C12115.58 (14)H13A—C13—H13B108.00
C11—C12—C13110.93 (13)Cl1—C14—H14A109.00
C12—C13—C14111.62 (13)Cl1—C14—H14B109.00
Cl1—C14—C13110.86 (11)C13—C14—H14A109.00
N1—C2—H2125.00C13—C14—H14B109.00
C3—C2—H2125.00H14A—C14—H14B108.00
C8—N1—C2—C30.28 (18)C5—C4—C9—C80.9 (2)
C2—N1—C8—C7179.69 (16)C4—C5—C6—C70.8 (2)
C2—N1—C8—C90.39 (17)C10—C5—C6—C7178.90 (14)
N1—C2—C3—C90.05 (18)C5—C6—C7—C80.2 (2)
N1—C2—C3—C11179.18 (15)C6—C7—C8—N1179.00 (16)
C2—C3—C9—C4178.35 (16)C6—C7—C8—C90.9 (2)
C2—C3—C9—C80.19 (17)N1—C8—C9—C30.35 (17)
C11—C3—C9—C40.9 (3)N1—C8—C9—C4178.43 (14)
C11—C3—C9—C8179.47 (14)C7—C8—C9—C3179.72 (14)
C2—C3—C11—C121.8 (2)C7—C8—C9—C41.5 (2)
C9—C3—C11—C12179.05 (14)C3—C11—C12—C13179.79 (13)
C9—C4—C5—C60.2 (2)C11—C12—C13—C14179.04 (13)
C9—C4—C5—C10179.49 (14)C12—C13—C14—Cl1178.05 (11)
C5—C4—C9—C3179.31 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···N2i0.787 (19)2.263 (19)3.039 (2)168.7 (19)
C4—H4···Cl1ii0.952.803.7497 (18)178
Symmetry codes: (i) x, y+1, z; (ii) x+1, y1/2, z+1/2.
 

References

First citationManikandan, 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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