addenda and errata
3-(4-Chlorobutyl)-3H-indole-5-carbonitrile. Corrigendum
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
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.
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.
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Supporting information
CCDC references: 1573008-1573009; 1573008; 1573009
https://doi.org/10.1107/S2414314617011324/hg9020sup1.cif
contains datablocks global, shelx. DOI:Structure factors: contains datablock shelx. DOI: https://doi.org/10.1107/S2414314617011324/hg9020sup1.hkl
Data collection: APEX2 (Bruker, 2008); cell
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).C13H13ClN2 | F(000) = 488 |
Mr = 232.70 | Dx = 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 |
Bruker APEXII diffractometer | 1632 reflections with I > 2σ(I) |
Detector resolution: 18.4 pixels mm-1 | Rint = 0.039 |
ω scans | θmax = 24.6°, θmin = 2.6° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2008) | h = −10→10 |
Tmin = 0.618, Tmax = 0.745 | k = −10→10 |
7342 measured reflections | l = −17→16 |
1952 independent reflections |
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 | Δρmax = 0.29 e Å−3 |
149 parameters | Δρmin = −0.24 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | ||
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* |
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) |
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) |
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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