Crystal structure of 1-[(6-chloro­pyridin-3-yl)sulfon­yl]-1,2,3,4-tetra­hydro­quinoline

S Jeyaseelan; H R Rajegowda; R Britto Dominic Rayan; P Raghavendra Kumar; B S Palakshamurthy

doi:10.1107/S2056989015008099

. 2015 May 23;71(Pt 6):660–662. doi: 10.1107/S2056989015008099

Crystal structure of 1-[(6-chloropyridin-3-yl)sulfonyl]-1,2,3,4-tetrahydroquinoline

S Jeyaseelan ^a,^*, H R Rajegowda ^b, R Britto Dominic Rayan ^c, P Raghavendra Kumar ^b, B S Palakshamurthy ^d

PMCID: PMC4459366 PMID: 26090144

In the crystal structure of 1-[(6-chloropyridin-3-yl)sulfonyl]-1,2,3,4-tetrahydroquinoline, the tetrahydropyridine ring of the quinoline system adopts a half-chair conformation and the bond-angle sum at the N atom is 350.0°.

Keywords: crystal structure; 1,2,3,4-tetrahydroquinoline; C—H⋯O interactions; pharmacological activity

Abstract

The tetrahydropyridine ring of the quinoline system in the title compound, C₁₄H₁₃ClN₂O₂S, adopts a half-chair conformation with the bond-angle sum at the N atom being 350.0°. The dihedral angle between the least-squares planes of the two aromatic rings is 50.13 (11)°. In the crystal, inversion dimers linked by pairs of C—H⋯O hydrogen bonds generate R ₂ ²(10) loops. Additional intermolecular C—H⋯O hydrogen bonds generate C(7) chains along [100].

Chemical context

1,2,3,4-Tetrahydroquinoline derivatives play a vital role in developing pharmacological agents and they have been considered as potential drugs (White et al., 1994 ▸; Kokwaro & Taylor, 1990 ▸; Omura & Nakagawa, 1981 ▸) and also antagonists for N-methyl-d-aspartate (NMDA) receptors at the glycine recognition site (Cai et al., 1996 ▸).

Recently, we have synthesized a series of 1,2,3,4-tetrahydroquinoline derivatives and a few molecules in fact exhibit pharmacological activity (unpublished results). In a continuation of our work on the derivatives of 1,2,3,4-tetrahydroquinolines (Jeyaseelan et al., 2014 ▸, 2015a ▸,b ▸), we report herein the synthesis and crystal structure of 1-[(6-chloropyridin-3-yl)sulfonyl]-1,2,3,4-tetrahydroquinoline, (I).

Structural commentary

The molecular structure of compound (I) is shown in Fig. 1 ▸. The dihedral angle between the planes of the aromatic rings is 50.13 (11)°. In comparison, the dihedral angle in the 1-tosyl-1,2,3,4-tetrahydroquinoline, (II), is 47.74 (9)° (Jeyaseelan et al., 2014 ▸), and in 1-benzylsulfonyl-1,2,3,4-tetrahydroquinoline, (III), it is 74.15 (10)° (Jeyaseelan et al., 2015b ▸). In the structures of compounds (II), (III) and 1-methanesulfonyl-1,2,3,4-tetrahydroquinoline, (IV) (Jeyaseelan et al., 2015a ▸), the tetrahydropyridine (C1/C6–C9/N1) ring is in a half-chair conformation, with the methylene C9 atom as the flap. However, the bond-angle sums at the N atom in (I), (II), (III) and (IV) differ somehow, with values of 350.0, 350.2, 354.61 and 347.9°, respectively.

The molecular structure of the title compound, showing displacement ellipsoids drawn at the 50% probability level.

Supramolecular features

In the crystal, inversion dimers linked by pairs of C11—H11⋯O2 hydrogen bonds generate Inline graphic (10) loops. In addition, molecules are linked by C7—H7A⋯O1 hydrogen bonds, generating C(7) chains along [100], as shown in Fig. 2 ▸. Numerical values of these interactions are compiled in Table 1 ▸.

The molecular packing of the title compound. Dashed lines indicate the pairs of C—H⋯O hydrogen bonds which link the molecules into inversion dimers with (10) ring motifs and forming C(7) chains along [100].

Table 1. Hydrogen-bond geometry (, ).

DHA	DH	HA	D A	DHA
C11H11O2ⁱ	0.93	2.60	3.309(3)	134
C7H7AO1ⁱⁱ	0.97	2.66	3.586(5)	160

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Symmetry codes: (i) Inline graphic ; (ii) .

Synthesis and crystallization

To an ice-cold solution of 1,2,3,4-tetrahydroquinoline (1.332 g, 10 mmol) and triethylamine (1.518 g, 15 mmol) in dichloromethane (50 ml), a solution of 6-chloropyridine-3-sulfonyl chloride (2.332 g, 11 mmol) in dichloromethane (20 ml) was added dropwise and stirred for 30 min. The reaction mixture was diluted with dichloromethane (150 ml), the organic layer washed with aqueous 5% NaHCO₃ solution and brine, and dried over anhydrous Na₂SO₄. The solvent was evaporated under reduced pressure to give 1-[(6-chloropyridin-3-yl)sulfonyl]-1,2,3,4-tetrahydroquinoline, (I). The product was recrystallized from a mixture of dichloromethane and n-hexane (1:1 v/v) to obtain crystals suitable for X-ray diffraction studies.

Refinement details

Crystal data, data collection and structure refinement details are summarized in Table 2 ▸. H atoms were positioned with idealized geometry using a riding-model approximation, with C—H = 0.93 Å and U _iso(H) = 1.2U _eq(C) for aromatic H atoms and with C—H = 0.97 Å and U _iso(H) = 1.2U _eq(C) for methylene H atoms.

Table 2. Experimental details.

Crystal data
Chemical formula	C₁₄H₁₃ClN₂O₂S
M _r	308.77
Crystal system, space group	Triclinic, P
Temperature (K)	296
a, b, c ()	6.5661(10), 10.2595(18), 11.3490(19)
, , ()	69.101(7), 88.219(7), 77.238(7)
V (³)	695.6(2)
Z	2
Radiation type	Mo K
(mm¹)	0.43
Crystal size (mm)	0.23 0.18 0.16

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2013 ▸)
T _min, T _max	0.912, 0.934
No. of measured, independent and observed [I > 2(I)] reflections	9865, 2454, 1980
R _int	0.053
(sin /)_max (¹)	0.595

Refinement
R[F ² > 2(F ²)], wR(F ²), S	0.050, 0.146, 1.09
No. of reflections	2454
No. of parameters	181
H-atom treatment	H-atom parameters constrained
_max, _min (e ³)	0.59, 0.43

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Computer programs: APEX2 and SAINT (Bruker, 2013 ▸), SHELXS97 (Sheldrick, 2008 ▸), SHELXL2014 (Sheldrick, 2015 ▸), ORTEP-3 for Windows (Farrugia, 2012 ▸) and Mercury (Macrae et al., 2008 ▸).

Supplementary Material

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S2056989015008099/wm5147sup1.cif

e-71-00660-sup1.cif^{(336.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015008099/wm5147Isup2.hkl

e-71-00660-Isup2.hkl^{(134.9KB, hkl)}

Click here for additional data file.^{(5.2KB, cml)}

Supporting information file. DOI: 10.1107/S2056989015008099/wm5147Isup3.cml

CCDC reference: 1061311

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

Acknowledgments

SJ thanks the Vision Group on Science and Technology, Government of Karnataka, for the award of a major project under the CISE scheme (reference No. VGST/CISE/GRD-192/2013–14), and the Indian Institute of Science, Bangalore, for extending the XRD facility.

supplementary crystallographic information

Crystal data

C₁₄H₁₃ClN₂O₂S	F(000) = 320
M_r = 308.77	prism
Triclinic, P1	D_x = 1.474 Mg m⁻³
Hall symbol: -P 1	Melting point: 413 K
a = 6.5661 (10) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.2595 (18) Å	Cell parameters from 1980 reflections
c = 11.3490 (19) Å	θ = 1.9–25.0°
α = 69.101 (7)°	µ = 0.43 mm⁻¹
β = 88.219 (7)°	T = 296 K
γ = 77.238 (7)°	Prism, colourless
V = 695.6 (2) Å³	0.23 × 0.18 × 0.16 mm
Z = 2

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Data collection

Bruker APEXII CCD diffractometer	2454 independent reflections
Radiation source: fine-focus sealed tube	1980 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.053
Detector resolution: 2.01 pixels mm^-1	θ_max = 25.0°, θ_min = 1.9°
phi and ω scans	h = −7→7
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −12→12
T_min = 0.912, T_max = 0.934	l = −13→13
9865 measured reflections

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Refinement

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.146	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0677P)² + 0.3614P] where P = (F_o² + 2F_c²)/3
2454 reflections	(Δ/σ)_max < 0.001
181 parameters	Δρ_max = 0.59 e Å⁻³
0 restraints	Δρ_min = −0.43 e Å⁻³
0 constraints

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Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

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

	x	y	z	U_iso*/U_eq
O1	0.3014 (3)	0.1696 (3)	0.3092 (2)	0.0753 (7)
S	0.40371 (11)	0.28345 (8)	0.24768 (6)	0.0562 (3)
Cl1	1.24374 (14)	0.01308 (10)	0.08760 (9)	0.0853 (3)
C10	0.6392 (4)	0.2111 (3)	0.1933 (2)	0.0479 (6)
N1	0.4673 (3)	0.3394 (2)	0.35739 (19)	0.0532 (6)
O2	0.3005 (3)	0.4047 (2)	0.14401 (19)	0.0712 (6)
C11	0.7513 (4)	0.2997 (3)	0.1091 (2)	0.0504 (6)
H11	0.6991	0.3983	0.0764	0.060*
N2	0.9018 (4)	0.0058 (3)	0.2047 (2)	0.0657 (7)
C1	0.5901 (4)	0.4468 (3)	0.3217 (2)	0.0479 (6)
C13	1.0055 (4)	0.0935 (3)	0.1264 (2)	0.0545 (7)
C6	0.7874 (4)	0.4136 (3)	0.3794 (3)	0.0542 (7)
C12	0.9387 (4)	0.2403 (3)	0.0750 (3)	0.0545 (7)
H12	1.0188	0.2965	0.0190	0.065*
C14	0.7193 (5)	0.0656 (3)	0.2371 (3)	0.0615 (8)
H14	0.6417	0.0064	0.2921	0.074*
C2	0.5110 (5)	0.5812 (3)	0.2320 (3)	0.0678 (8)
H2	0.3760	0.6042	0.1966	0.081*
C5	0.9038 (5)	0.5175 (4)	0.3419 (3)	0.0690 (8)
H5	1.0362	0.4975	0.3798	0.083*
C9	0.5138 (5)	0.2322 (4)	0.4875 (3)	0.0733 (10)
H9A	0.4544	0.2766	0.5470	0.088*
H9B	0.4466	0.1542	0.4963	0.088*
C3	0.6339 (7)	0.6804 (3)	0.1957 (3)	0.0812 (10)
H3	0.5830	0.7694	0.1335	0.097*
C4	0.8292 (6)	0.6494 (4)	0.2502 (3)	0.0766 (10)
H4	0.9112	0.7169	0.2255	0.092*
C7	0.8693 (6)	0.2732 (4)	0.4825 (4)	0.0796 (10)
H7A	0.9980	0.2263	0.4563	0.096*
H7B	0.9042	0.2917	0.5566	0.096*
C8	0.7326 (7)	0.1753 (5)	0.5187 (4)	0.124 (2)
H8A	0.7792	0.1037	0.4804	0.149*
H8B	0.7507	0.1261	0.6095	0.149*

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Atomic displacement parameters (Å²)

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0680 (14)	0.0963 (16)	0.0687 (13)	−0.0494 (13)	0.0085 (11)	−0.0202 (12)
S	0.0469 (4)	0.0698 (5)	0.0465 (4)	−0.0217 (3)	−0.0027 (3)	−0.0090 (3)
Cl1	0.0736 (6)	0.0948 (7)	0.0859 (6)	0.0056 (5)	−0.0027 (5)	−0.0446 (5)
C10	0.0520 (15)	0.0511 (15)	0.0373 (12)	−0.0186 (12)	−0.0063 (11)	−0.0069 (11)
N1	0.0489 (12)	0.0633 (14)	0.0406 (11)	−0.0183 (11)	0.0032 (9)	−0.0072 (10)
O2	0.0547 (12)	0.0850 (15)	0.0553 (11)	−0.0067 (11)	−0.0148 (9)	−0.0068 (11)
C11	0.0571 (16)	0.0441 (14)	0.0429 (13)	−0.0133 (12)	−0.0019 (12)	−0.0056 (11)
N2	0.0813 (19)	0.0509 (14)	0.0591 (15)	−0.0116 (13)	−0.0060 (13)	−0.0140 (12)
C1	0.0511 (15)	0.0463 (14)	0.0435 (13)	−0.0087 (12)	0.0095 (11)	−0.0146 (11)
C13	0.0566 (16)	0.0595 (17)	0.0472 (14)	−0.0088 (13)	−0.0096 (12)	−0.0203 (13)
C6	0.0566 (16)	0.0517 (16)	0.0551 (15)	−0.0155 (13)	0.0029 (13)	−0.0184 (13)
C12	0.0561 (16)	0.0596 (17)	0.0482 (14)	−0.0218 (14)	0.0053 (12)	−0.0149 (13)
C14	0.078 (2)	0.0509 (17)	0.0508 (15)	−0.0255 (16)	0.0011 (14)	−0.0056 (13)
C2	0.0673 (19)	0.0558 (18)	0.0628 (18)	−0.0001 (15)	0.0048 (15)	−0.0088 (14)
C5	0.070 (2)	0.070 (2)	0.077 (2)	−0.0312 (17)	0.0105 (16)	−0.0290 (17)
C9	0.079 (2)	0.093 (2)	0.0399 (15)	−0.0443 (19)	0.0005 (14)	−0.0004 (15)
C3	0.105 (3)	0.0411 (16)	0.081 (2)	−0.0057 (18)	0.025 (2)	−0.0101 (15)
C4	0.098 (3)	0.060 (2)	0.084 (2)	−0.0356 (19)	0.033 (2)	−0.0315 (18)
C7	0.066 (2)	0.068 (2)	0.086 (2)	−0.0170 (17)	−0.0195 (17)	−0.0029 (17)
C8	0.110 (3)	0.118 (3)	0.089 (3)	−0.050 (3)	−0.042 (3)	0.047 (3)

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Geometric parameters (Å, º)

O1—S	1.428 (2)	C6—C5	1.385 (4)
S—O2	1.423 (2)	C6—C7	1.492 (4)
S—O1	1.428 (2)	C12—H12	0.9300
S—N1	1.644 (2)	C14—H14	0.9300
S—C10	1.756 (3)	C2—C3	1.378 (5)
Cl1—C13	1.723 (3)	C2—H2	0.9300
C10—C14	1.376 (4)	C5—C4	1.374 (5)
C10—C11	1.383 (3)	C5—H5	0.9300
N1—C1	1.443 (3)	C9—C8	1.430 (5)
N1—C9	1.484 (3)	C9—H9A	0.9700
C11—C12	1.358 (4)	C9—H9B	0.9700
C11—H11	0.9300	C3—C4	1.362 (5)
N2—C13	1.314 (4)	C3—H3	0.9300
N2—C14	1.325 (4)	C4—H4	0.9300
C1—C2	1.386 (4)	C7—C8	1.437 (5)
C1—C6	1.387 (4)	C7—H7A	0.9700
C13—C12	1.378 (4)	C8—H8A	0.9700

O2—S—O1	120.12 (13)	C3—C2—C1	119.5 (3)
O2—S—N1	108.30 (13)	C3—C2—H2	120.2
O1—S—N1	106.51 (12)	C1—C2—H2	120.2
O2—S—C10	106.62 (12)	C4—C5—C6	121.9 (3)
O1—S—C10	107.97 (14)	C4—C5—H5	119.1
N1—S—C10	106.63 (12)	C6—C5—H5	119.1
C14—C10—C11	118.8 (3)	C8—C9—N1	113.3 (3)
C14—C10—S	120.6 (2)	C8—C9—H9A	108.9
C11—C10—S	120.6 (2)	N1—C9—H9A	108.9
C1—N1—C9	115.2 (2)	C8—C9—H9B	108.9
C1—N1—S	117.64 (16)	N1—C9—H9B	108.9
C9—N1—S	117.2 (2)	H9A—C9—H9B	107.7
C12—C11—C10	118.9 (3)	C4—C3—C2	120.7 (3)
C12—C11—H11	120.6	C4—C3—H3	119.6
C10—C11—H11	120.6	C2—C3—H3	119.6
C13—N2—C14	116.3 (2)	C3—C4—C5	119.4 (3)
C2—C1—C6	120.7 (3)	C3—C4—H4	120.3
C2—C1—N1	120.4 (3)	C5—C4—H4	120.3
C6—C1—N1	118.8 (2)	C8—C7—C6	116.5 (3)
N2—C13—C12	125.4 (3)	C8—C7—H7A	108.2
N2—C13—Cl1	115.3 (2)	C6—C7—H7A	108.2
C12—C13—Cl1	119.2 (2)	C8—C7—H7B	108.2
C5—C6—C1	117.8 (3)	C6—C7—H7B	108.2
C5—C6—C7	120.7 (3)	H7A—C7—H7B	107.3
C1—C6—C7	121.5 (2)	C9—C8—C7	118.0 (4)
C11—C12—C13	117.4 (3)	C9—C8—H8A	107.8
C11—C12—H12	121.3	C7—C8—H8A	107.8
C13—C12—H12	121.3	C9—C8—H8B	107.8
N2—C14—C10	123.1 (3)	C7—C8—H8B	107.8
N2—C14—H14	118.4	H8A—C8—H8B	107.1
C10—C14—H14	118.4

O2—S—C10—C14	−145.4 (2)	C9—N1—C1—C6	27.0 (4)
O2—S—C10—C14	−145.4 (2)	S—N1—C1—C6	−117.9 (2)
O1—S—C10—C14	−15.0 (3)	C14—N2—C13—C12	−1.0 (4)
O1—S—C10—C14	−15.0 (3)	C14—N2—C13—Cl1	179.2 (2)
O1—S—C10—C14	−15.0 (3)	C2—C1—C6—C5	−1.8 (4)
N1—S—C10—C14	99.1 (2)	N1—C1—C6—C5	178.8 (2)
O2—S—C10—C11	37.0 (2)	C2—C1—C6—C7	175.7 (3)
O2—S—C10—C11	37.0 (2)	N1—C1—C6—C7	−3.7 (4)
O1—S—C10—C11	167.3 (2)	C10—C11—C12—C13	0.4 (4)
O1—S—C10—C11	167.3 (2)	N2—C13—C12—C11	0.9 (4)
O1—S—C10—C11	167.3 (2)	Cl1—C13—C12—C11	−179.2 (2)
N1—S—C10—C11	−78.6 (2)	C13—N2—C14—C10	−0.3 (4)
O2—S—N1—C1	−54.9 (2)	C11—C10—C14—N2	1.5 (4)
O2—S—N1—C1	−54.9 (2)	S—C10—C14—N2	−176.1 (2)
O1—S—N1—C1	174.7 (2)	C6—C1—C2—C3	3.1 (4)
O1—S—N1—C1	174.7 (2)	N1—C1—C2—C3	−177.6 (3)
O1—S—N1—C1	174.7 (2)	C1—C6—C5—C4	−0.3 (5)
C10—S—N1—C1	59.5 (2)	C7—C6—C5—C4	−177.8 (3)
O2—S—N1—C9	161.0 (2)	C1—N1—C9—C8	−46.6 (5)
O2—S—N1—C9	161.0 (2)	S—N1—C9—C8	98.4 (4)
O1—S—N1—C9	30.5 (2)	C1—C2—C3—C4	−2.3 (5)
O1—S—N1—C9	30.5 (2)	C2—C3—C4—C5	0.2 (5)
O1—S—N1—C9	30.5 (2)	C6—C5—C4—C3	1.1 (5)
C10—S—N1—C9	−84.6 (2)	C5—C6—C7—C8	177.1 (4)
C14—C10—C11—C12	−1.6 (4)	C1—C6—C7—C8	−0.3 (6)
S—C10—C11—C12	176.12 (19)	N1—C9—C8—C7	43.5 (6)
C9—N1—C1—C2	−152.4 (3)	C6—C7—C8—C9	−20.5 (7)
S—N1—C1—C2	62.8 (3)

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Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O2ⁱ	0.93	2.60	3.309 (3)	134
C7—H7A···O1ⁱⁱ	0.97	2.66	3.586 (5)	160

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

References

Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
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Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.
Jeyaseelan, S., Asha, K. V., Venkateshappa, G., Raghavendrakumar, P. & Palakshamurthy, B. S. (2014). Acta Cryst. E70, o1176. [DOI] [PMC free article] [PubMed]
Jeyaseelan, S., Nagendra Babu, S. L., Venkateshappa, G., Raghavendra Kumar, P. & Palakshamurthy, B. S. (2015a). Acta Cryst. E71, o20. [DOI] [PMC free article] [PubMed]
Jeyaseelan, S., Sowmya, B. R., Venkateshappa, G., Raghavendra Kumar, P. & Palakshamurthy, B. S. (2015b). Acta Cryst. E71, o249–o250. [DOI] [PMC free article] [PubMed]
Kokwaro, G. O. & Taylor, G. (1990). Drug Chem. Toxicol. 13, 347–354. [DOI] [PubMed]
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470.
Ōmura, S. & Nakagawa, A. (1981). Tetrahedron Lett. 22, 2199–2202.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8.
White, J. D., Yager, K. M. & Yakura, T. (1994). J. Am. Chem. Soc. 116, 1831–1838.

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S2056989015008099/wm5147sup1.cif

e-71-00660-sup1.cif^{(336.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015008099/wm5147Isup2.hkl

e-71-00660-Isup2.hkl^{(134.9KB, hkl)}

Click here for additional data file.^{(5.2KB, cml)}

Supporting information file. DOI: 10.1107/S2056989015008099/wm5147Isup3.cml

CCDC reference: 1061311

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

[bb1] Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.

[bb2] Cai, S. X., Zhou, Z. L., Huang, J. C., Whittemore, E. R., Egbuwoku, Z. O., Lü, Y., Hawkinson, J. E., Woodward, R. M., Weber, E. & Keana, J. F. W. (1996). J. Med. Chem. 39, 3248–3255. [DOI] [PubMed]

[bb3] Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.

[bb4] Jeyaseelan, S., Asha, K. V., Venkateshappa, G., Raghavendrakumar, P. & Palakshamurthy, B. S. (2014). Acta Cryst. E70, o1176. [DOI] [PMC free article] [PubMed]

[bb5] Jeyaseelan, S., Nagendra Babu, S. L., Venkateshappa, G., Raghavendra Kumar, P. & Palakshamurthy, B. S. (2015a). Acta Cryst. E71, o20. [DOI] [PMC free article] [PubMed]

[bb6] Jeyaseelan, S., Sowmya, B. R., Venkateshappa, G., Raghavendra Kumar, P. & Palakshamurthy, B. S. (2015b). Acta Cryst. E71, o249–o250. [DOI] [PMC free article] [PubMed]

[bb7] Kokwaro, G. O. & Taylor, G. (1990). Drug Chem. Toxicol. 13, 347–354. [DOI] [PubMed]

[bb8] Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470.

[bb9] Ōmura, S. & Nakagawa, A. (1981). Tetrahedron Lett. 22, 2199–2202.

[bb10] Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]

[bb11] Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8.

[bb12] White, J. D., Yager, K. M. & Yakura, T. (1994). J. Am. Chem. Soc. 116, 1831–1838.

PERMALINK

Crystal structure of 1-[(6-chloropyridin-3-yl)sulfonyl]-1,2,3,4-tetrahydroquinoline

S Jeyaseelan

H R Rajegowda

R Britto Dominic Rayan

P Raghavendra Kumar

B S Palakshamurthy

Abstract

Chemical context

Structural commentary

Figure 1.

Supramolecular features