organic compounds
of [4-(chloromethyl)phenyl](4-hydroxypiperidin-1-yl)methanone
aPG and Research Department of Physics, Queen Mary's College, Chennai-4, Tamilnadu, India, bDepartment of Chemistry, Madras Christian College, Chennai-59, India, cSCRI, Anna hospital Campus, Chennai-106, Tamilnadu, India, and dAnna Siddha Medical College, Chennai-106, Tamilnadu, India
*Correspondence e-mail: guqmc@yahoo.com
The title compound, C13H16ClNO2, crystallized with two independent molecules in the (A and B). The piperidinol ring in molecule B is disordered over two positions with a site occupancy ratio of 0.667 (5):0.333 (5). In both molecules these rings have a chair conformation, including the minor component in molecule B. Their mean planes are inclined to the benzene ring by 45.57 (13)° in molecule A, and by 50.5 (4)° for the major component of the piperidine ring in molecule B. In the crystal, the individual molecules are linked by O—H⋯O hydrogen bonds, forming chains of A and B molecules along the [100] direction. The chains are interlinked by C—H⋯O hydrogen bonds, forming ribbons.
Keywords: crystal structure; piperidine derivative; hydrogen bonding.
CCDC reference: 1421009
1. Related literature
For the synthesis see: Revathi et al. (2015). For the biological activity of piperidine derivatives, see: Daly et al. (1986); Fodor et al. (1985); Campfield et al. (1995); Kozikowski et al. (1998); Brau et al. (2000); Bolzani et al. (1995); Gulluoglu et al. (2007). For related structures see: Revathi et al. (2015); Prathebha et al. (2015).
2. Experimental
2.1. Crystal data
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2.3. Refinement
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Data collection: APEX2 (Bruker, 2004); cell APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Bruno et al., 2002); software used to prepare material for publication: SHELXL2014.
Supporting information
CCDC reference: 1421009
10.1107/S2056989015016096/bg2567sup1.cif
contains datablocks I, New_Global_Publ_Block. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2056989015016096/bg2567Isup2.hkl
Supporting information file. DOI: 10.1107/S2056989015016096/bg2567Isup3.cml
The title compound was synthesized following a publish procedure (Revathi et al., (2015)). In a 250 ml roundbottomed flask 120 ml of ethylmethylketone was added to 4-hydroxypiperdine (0.02 mol) and stirred at room temperature. After 5 min triethylamine (0.04 mol) was added and the mixture was stirred for 15 min. Then 4-chloromethyl benzoylchloride(0.04 mol) was added and the reaction mixture was stirred at room temperature for ca 2 h. A white precipitate of triethylammoniumchloride was formed. It was filtered and the filtrate was evaporated to give the crude product. It was recrystallized twice from ethylmethylketone (yield: 82%) giving colourless block-like crystals of the title compound.
H atoms were positioned geometrically and treated as riding on their parent atoms and refined with, C—H distance of 0.93–0.98 Å, O—H distance of 0.82 Å with Uiso(H)= 1.5 Ueq(c-methyl),Uiso(H)= 1.5 Ueq(O) and Uiso(H)= 1.2Ueq(C) for other H atom. The piperidinol ring in one of the molecules is disordered over two positions with site occupancies in the ratio 67:33. The disorder was resolved by successive Fourier electron density maps and least squares refinements. Sum of the occupancies of the disordered components were restrained as 1 during
The bond distances in the disordered groups were restrained using SADI or DFIX with an effective standard deviation of 0.01 Å and 0.02 Å respectively, wherever necessary. Rigid group restraint(RIGU) with e.s.d.'s 0.002 Å and 0.004 Å was also applied to get satisfactory model of the disorder.Data collection: APEX2 (Bruker, 2004); cell
APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Bruno et al., 2002); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015).Fig. 1. The molecular structure of the title compound (left: molecula A; right: molecule B), with displacement ellipsoids drawn at the 30% probability level. | |
Fig. 2. The packing of the molecules in the crystal structure. The dashed lines indicate the hydrogen bonds. |
C13H16ClNO2 | Z = 4 |
Mr = 253.72 | F(000) = 536 |
Triclinic, P1 | Dx = 1.345 Mg m−3 |
a = 8.4131 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.6211 (4) Å | Cell parameters from 9919 reflections |
c = 15.6780 (6) Å | θ = 2.3–28.1° |
α = 80.917 (3)° | µ = 0.29 mm−1 |
β = 89.240 (2)° | T = 293 K |
γ = 88.395 (2)° | Block, colourless |
V = 1252.57 (8) Å3 | 0.35 × 0.30 × 0.25 mm |
Bruker Kappa APEXII CCD diffractometer | 4415 independent reflections |
Radiation source: fine-focus sealed tube | 3411 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
ω and φ scan | θmax = 25.0°, θmin = 1.3° |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | h = −10→10 |
Tmin = 0.902, Tmax = 0.943 | k = −11→11 |
28447 measured reflections | l = −18→18 |
Refinement on F2 | 111 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.045 | H-atom parameters constrained |
wR(F2) = 0.128 | w = 1/[σ2(Fo2) + (0.0477P)2 + 1.0906P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.001 |
4415 reflections | Δρmax = 0.45 e Å−3 |
371 parameters | Δρmin = −0.61 e Å−3 |
C13H16ClNO2 | γ = 88.395 (2)° |
Mr = 253.72 | V = 1252.57 (8) Å3 |
Triclinic, P1 | Z = 4 |
a = 8.4131 (3) Å | Mo Kα radiation |
b = 9.6211 (4) Å | µ = 0.29 mm−1 |
c = 15.6780 (6) Å | T = 293 K |
α = 80.917 (3)° | 0.35 × 0.30 × 0.25 mm |
β = 89.240 (2)° |
Bruker Kappa APEXII CCD diffractometer | 4415 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | 3411 reflections with I > 2σ(I) |
Tmin = 0.902, Tmax = 0.943 | Rint = 0.027 |
28447 measured reflections |
R[F2 > 2σ(F2)] = 0.045 | 111 restraints |
wR(F2) = 0.128 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.45 e Å−3 |
4415 reflections | Δρmin = −0.61 e Å−3 |
371 parameters |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C1 | 1.1123 (3) | 0.3281 (3) | −0.11147 (15) | 0.0386 (5) | |
C2 | 1.0000 (3) | 0.2251 (3) | −0.10479 (15) | 0.0413 (6) | |
H2 | 0.9657 | 0.1937 | −0.1544 | 0.050* | |
C3 | 0.9381 (3) | 0.1683 (3) | −0.02565 (16) | 0.0408 (6) | |
H3 | 0.8600 | 0.1011 | −0.0223 | 0.049* | |
C4 | 0.9916 (2) | 0.2108 (2) | 0.04902 (15) | 0.0347 (5) | |
C5 | 1.1051 (3) | 0.3129 (3) | 0.04244 (16) | 0.0409 (6) | |
H5 | 1.1425 | 0.3421 | 0.0921 | 0.049* | |
C6 | 1.1633 (3) | 0.3716 (3) | −0.03693 (16) | 0.0449 (6) | |
H6 | 1.2381 | 0.4416 | −0.0405 | 0.054* | |
C7 | 0.9414 (3) | 0.1401 (2) | 0.13670 (15) | 0.0369 (5) | |
C8 | 0.6599 (3) | 0.2173 (3) | 0.10907 (17) | 0.0449 (6) | |
H8A | 0.7011 | 0.2648 | 0.0544 | 0.054* | |
H8B | 0.6232 | 0.2885 | 0.1427 | 0.054* | |
C9 | 0.5227 (3) | 0.1276 (3) | 0.09289 (17) | 0.0480 (6) | |
H9A | 0.5571 | 0.0624 | 0.0546 | 0.058* | |
H9B | 0.4377 | 0.1872 | 0.0647 | 0.058* | |
C10 | 0.4611 (3) | 0.0460 (3) | 0.17647 (17) | 0.0448 (6) | |
H10 | 0.4214 | 0.1130 | 0.2133 | 0.054* | |
C11 | 0.5957 (3) | −0.0414 (3) | 0.22218 (19) | 0.0545 (7) | |
H11A | 0.6322 | −0.1113 | 0.1876 | 0.065* | |
H11B | 0.5578 | −0.0904 | 0.2772 | 0.065* | |
C12 | 0.7328 (3) | 0.0503 (3) | 0.23722 (16) | 0.0538 (7) | |
H12A | 0.6993 | 0.1144 | 0.2763 | 0.065* | |
H12B | 0.8201 | −0.0084 | 0.2637 | 0.065* | |
C13 | 1.1795 (3) | 0.3886 (3) | −0.19750 (17) | 0.0512 (7) | |
H13A | 1.1600 | 0.3256 | −0.2385 | 0.061* | |
H13B | 1.2937 | 0.3963 | −0.1928 | 0.061* | |
C14 | 0.3857 (3) | 0.4916 (3) | 0.28225 (15) | 0.0401 (6) | |
C15 | 0.3397 (3) | 0.3530 (3) | 0.30142 (16) | 0.0449 (6) | |
H15 | 0.2663 | 0.3191 | 0.2665 | 0.054* | |
C16 | 0.4011 (3) | 0.2651 (3) | 0.37143 (16) | 0.0423 (6) | |
H16 | 0.3673 | 0.1728 | 0.3841 | 0.051* | |
C17 | 0.5127 (3) | 0.3125 (2) | 0.42329 (14) | 0.0348 (5) | |
C18 | 0.5592 (3) | 0.4505 (3) | 0.40463 (15) | 0.0412 (6) | |
H18 | 0.6343 | 0.4836 | 0.4390 | 0.049* | |
C19 | 0.4949 (3) | 0.5397 (3) | 0.33533 (16) | 0.0418 (6) | |
H19 | 0.5252 | 0.6330 | 0.3242 | 0.050* | |
C20 | 0.5672 (3) | 0.2185 (3) | 0.50338 (15) | 0.0376 (5) | |
C26 | 0.3178 (3) | 0.5885 (3) | 0.20677 (17) | 0.0529 (7) | |
H26A | 0.3322 | 0.6854 | 0.2146 | 0.063* | |
H26B | 0.2045 | 0.5738 | 0.2036 | 0.063* | |
O1 | 1.04414 (19) | 0.0877 (2) | 0.18842 (11) | 0.0515 (5) | |
N1 | 0.7862 (2) | 0.1306 (2) | 0.15550 (12) | 0.0401 (5) | |
O2 | 0.3366 (2) | −0.0447 (2) | 0.16381 (16) | 0.0681 (6) | |
H2A | 0.2626 | 0.0017 | 0.1392 | 0.102* | |
O3 | 0.4671 (2) | 0.1695 (2) | 0.55717 (12) | 0.0556 (5) | |
Cl1 | 1.09363 (11) | 0.55854 (9) | −0.23667 (5) | 0.0747 (3) | |
Cl2 | 0.41251 (10) | 0.55824 (10) | 0.10800 (5) | 0.0706 (3) | |
C21 | 0.8443 (13) | 0.2288 (15) | 0.4478 (7) | 0.0369 (19) | 0.667 (5) |
H21A | 0.8004 | 0.2904 | 0.3983 | 0.044* | 0.667 (5) |
H21B | 0.8764 | 0.1400 | 0.4299 | 0.044* | 0.667 (5) |
C22 | 0.9860 (15) | 0.2956 (12) | 0.4818 (9) | 0.044 (2) | 0.667 (5) |
H22A | 1.0703 | 0.3027 | 0.4386 | 0.053* | 0.667 (5) |
H22B | 0.9558 | 0.3904 | 0.4907 | 0.053* | 0.667 (5) |
C23 | 1.0491 (9) | 0.2147 (8) | 0.5655 (5) | 0.0479 (19) | 0.667 (5) |
H23 | 1.0836 | 0.1191 | 0.5582 | 0.057* | 0.667 (5) |
C24 | 0.9138 (13) | 0.2112 (15) | 0.6311 (9) | 0.049 (2) | 0.667 (5) |
H24A | 0.9507 | 0.1668 | 0.6875 | 0.059* | 0.667 (5) |
H24B | 0.8774 | 0.3064 | 0.6354 | 0.059* | 0.667 (5) |
C25 | 0.7790 (15) | 0.1296 (10) | 0.6030 (5) | 0.043 (2) | 0.667 (5) |
H25A | 0.8151 | 0.0347 | 0.5977 | 0.052* | 0.667 (5) |
H25B | 0.6932 | 0.1240 | 0.6452 | 0.052* | 0.667 (5) |
O4 | 1.1723 (3) | 0.2855 (3) | 0.5966 (2) | 0.0623 (11) | 0.667 (5) |
H4 | 1.2493 | 0.2861 | 0.5639 | 0.093* | 0.667 (5) |
N2 | 0.7232 (8) | 0.2047 (16) | 0.5184 (5) | 0.034 (2) | 0.667 (5) |
C21' | 0.850 (3) | 0.210 (3) | 0.4530 (15) | 0.042 (5) | 0.333 (5) |
H21C | 0.8069 | 0.2460 | 0.3966 | 0.051* | 0.333 (5) |
H21D | 0.9095 | 0.1236 | 0.4483 | 0.051* | 0.333 (5) |
C22' | 0.967 (3) | 0.318 (3) | 0.4775 (18) | 0.040 (4) | 0.333 (5) |
H22C | 1.0482 | 0.3387 | 0.4333 | 0.048* | 0.333 (5) |
H22D | 0.9105 | 0.4054 | 0.4843 | 0.048* | 0.333 (5) |
C23' | 1.0410 (17) | 0.2493 (16) | 0.5636 (10) | 0.044 (3) | 0.333 (5) |
H23' | 1.1000 | 0.3196 | 0.5883 | 0.053* | 0.333 (5) |
C24' | 0.915 (3) | 0.184 (3) | 0.6302 (19) | 0.044 (4) | 0.333 (5) |
H24C | 0.9685 | 0.1185 | 0.6751 | 0.053* | 0.333 (5) |
H24D | 0.8646 | 0.2576 | 0.6571 | 0.053* | 0.333 (5) |
C25' | 0.787 (3) | 0.105 (2) | 0.5893 (10) | 0.036 (3) | 0.333 (5) |
H25C | 0.8326 | 0.0158 | 0.5781 | 0.043* | 0.333 (5) |
H25D | 0.7011 | 0.0843 | 0.6307 | 0.043* | 0.333 (5) |
O4' | 1.1380 (7) | 0.1335 (6) | 0.5593 (4) | 0.0532 (19) | 0.333 (5) |
H4' | 1.1397 | 0.1163 | 0.5097 | 0.080* | 0.333 (5) |
N2' | 0.7230 (17) | 0.178 (3) | 0.5116 (12) | 0.034 (4) | 0.333 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0315 (12) | 0.0437 (14) | 0.0382 (13) | 0.0044 (10) | 0.0024 (10) | 0.0000 (10) |
C2 | 0.0428 (14) | 0.0448 (14) | 0.0359 (13) | 0.0018 (11) | −0.0064 (10) | −0.0049 (11) |
C3 | 0.0367 (13) | 0.0384 (13) | 0.0454 (14) | −0.0061 (10) | −0.0063 (10) | 0.0013 (11) |
C4 | 0.0264 (11) | 0.0372 (12) | 0.0381 (12) | 0.0032 (9) | −0.0023 (9) | 0.0006 (10) |
C5 | 0.0358 (13) | 0.0497 (15) | 0.0375 (13) | −0.0078 (11) | −0.0008 (10) | −0.0066 (11) |
C6 | 0.0377 (13) | 0.0499 (15) | 0.0468 (14) | −0.0137 (11) | 0.0038 (11) | −0.0047 (12) |
C7 | 0.0300 (12) | 0.0394 (13) | 0.0391 (13) | −0.0008 (10) | −0.0044 (10) | 0.0003 (10) |
C8 | 0.0323 (13) | 0.0430 (14) | 0.0540 (15) | 0.0056 (10) | −0.0027 (11) | 0.0084 (12) |
C9 | 0.0319 (13) | 0.0584 (17) | 0.0506 (15) | 0.0033 (11) | −0.0103 (11) | 0.0008 (12) |
C10 | 0.0298 (12) | 0.0462 (15) | 0.0581 (16) | −0.0023 (10) | 0.0036 (11) | −0.0075 (12) |
C11 | 0.0359 (14) | 0.0597 (17) | 0.0589 (17) | −0.0007 (12) | 0.0089 (12) | 0.0180 (14) |
C12 | 0.0344 (13) | 0.082 (2) | 0.0379 (14) | −0.0010 (13) | −0.0006 (11) | 0.0131 (13) |
C13 | 0.0474 (15) | 0.0620 (18) | 0.0423 (14) | −0.0006 (13) | 0.0078 (12) | −0.0031 (13) |
C14 | 0.0346 (12) | 0.0452 (14) | 0.0391 (13) | 0.0069 (10) | 0.0037 (10) | −0.0038 (11) |
C15 | 0.0391 (13) | 0.0524 (16) | 0.0441 (14) | −0.0019 (11) | −0.0103 (11) | −0.0096 (12) |
C16 | 0.0398 (13) | 0.0411 (14) | 0.0455 (14) | −0.0081 (11) | −0.0041 (11) | −0.0031 (11) |
C17 | 0.0282 (11) | 0.0429 (13) | 0.0326 (12) | −0.0039 (10) | 0.0034 (9) | −0.0037 (10) |
C18 | 0.0366 (13) | 0.0478 (15) | 0.0402 (13) | −0.0089 (11) | −0.0007 (10) | −0.0085 (11) |
C19 | 0.0419 (13) | 0.0362 (13) | 0.0458 (14) | −0.0024 (10) | 0.0060 (11) | −0.0025 (11) |
C20 | 0.0337 (12) | 0.0430 (14) | 0.0355 (12) | −0.0081 (10) | 0.0015 (10) | −0.0027 (10) |
C26 | 0.0471 (15) | 0.0555 (17) | 0.0517 (16) | 0.0108 (13) | −0.0020 (12) | 0.0031 (13) |
O1 | 0.0293 (9) | 0.0739 (13) | 0.0442 (10) | 0.0017 (8) | −0.0065 (7) | 0.0121 (9) |
N1 | 0.0266 (10) | 0.0491 (12) | 0.0393 (11) | 0.0000 (8) | −0.0023 (8) | 0.0093 (9) |
O2 | 0.0403 (11) | 0.0565 (12) | 0.1079 (18) | −0.0095 (9) | −0.0029 (11) | −0.0127 (12) |
O3 | 0.0340 (9) | 0.0783 (13) | 0.0472 (10) | −0.0111 (9) | 0.0048 (8) | 0.0139 (9) |
Cl1 | 0.0836 (6) | 0.0706 (5) | 0.0591 (5) | 0.0037 (4) | 0.0180 (4) | 0.0208 (4) |
Cl2 | 0.0733 (5) | 0.0911 (6) | 0.0425 (4) | 0.0114 (4) | −0.0080 (3) | 0.0028 (4) |
C21 | 0.034 (3) | 0.038 (4) | 0.037 (3) | 0.001 (2) | 0.008 (2) | −0.001 (2) |
C22 | 0.029 (3) | 0.048 (4) | 0.054 (4) | −0.004 (3) | 0.006 (2) | −0.001 (3) |
C23 | 0.035 (3) | 0.053 (4) | 0.055 (3) | −0.002 (2) | −0.0049 (19) | −0.006 (3) |
C24 | 0.040 (3) | 0.067 (6) | 0.039 (3) | 0.001 (3) | −0.009 (2) | −0.003 (3) |
C25 | 0.041 (3) | 0.051 (4) | 0.034 (3) | 0.000 (3) | 0.000 (2) | 0.005 (3) |
O4 | 0.0366 (16) | 0.082 (2) | 0.074 (2) | −0.0104 (14) | −0.0054 (13) | −0.0299 (17) |
N2 | 0.029 (2) | 0.041 (6) | 0.031 (2) | −0.0078 (18) | 0.0001 (16) | 0.001 (3) |
C21' | 0.037 (5) | 0.054 (9) | 0.033 (5) | −0.003 (5) | −0.001 (4) | 0.002 (5) |
C22' | 0.027 (6) | 0.047 (6) | 0.041 (5) | 0.001 (4) | −0.001 (4) | 0.005 (4) |
C23' | 0.032 (5) | 0.050 (5) | 0.046 (5) | 0.005 (3) | −0.004 (3) | 0.003 (3) |
C24' | 0.040 (5) | 0.047 (7) | 0.043 (5) | 0.003 (4) | 0.000 (4) | −0.001 (4) |
C25' | 0.034 (5) | 0.037 (5) | 0.035 (5) | 0.002 (4) | 0.009 (4) | 0.001 (4) |
O4' | 0.035 (3) | 0.046 (3) | 0.075 (4) | 0.004 (3) | 0.003 (2) | 0.000 (3) |
N2' | 0.038 (5) | 0.027 (8) | 0.036 (4) | −0.004 (3) | 0.002 (3) | −0.002 (4) |
C1—C6 | 1.379 (3) | C18—H18 | 0.9300 |
C1—C2 | 1.380 (3) | C19—H19 | 0.9300 |
C1—C13 | 1.493 (3) | C20—O3 | 1.233 (3) |
C2—C3 | 1.376 (3) | C20—N2 | 1.335 (7) |
C2—H2 | 0.9300 | C20—N2' | 1.359 (14) |
C3—C4 | 1.384 (3) | C26—Cl2 | 1.793 (3) |
C3—H3 | 0.9300 | C26—H26A | 0.9700 |
C4—C5 | 1.380 (3) | C26—H26B | 0.9700 |
C4—C7 | 1.495 (3) | O2—H2A | 0.8200 |
C5—C6 | 1.373 (3) | C21—N2 | 1.489 (10) |
C5—H5 | 0.9300 | C21—C22 | 1.512 (8) |
C6—H6 | 0.9300 | C21—H21A | 0.9700 |
C7—O1 | 1.235 (3) | C21—H21B | 0.9700 |
C7—N1 | 1.337 (3) | C22—C23 | 1.511 (8) |
C8—N1 | 1.461 (3) | C22—H22A | 0.9700 |
C8—C9 | 1.508 (3) | C22—H22B | 0.9700 |
C8—H8A | 0.9700 | C23—O4 | 1.391 (8) |
C8—H8B | 0.9700 | C23—C24 | 1.521 (9) |
C9—C10 | 1.510 (4) | C23—H23 | 0.9800 |
C9—H9A | 0.9700 | C24—C25 | 1.505 (8) |
C9—H9B | 0.9700 | C24—H24A | 0.9700 |
C10—O2 | 1.417 (3) | C24—H24B | 0.9700 |
C10—C11 | 1.511 (4) | C25—N2 | 1.483 (9) |
C10—H10 | 0.9800 | C25—H25A | 0.9700 |
C11—C12 | 1.514 (4) | C25—H25B | 0.9700 |
C11—H11A | 0.9700 | O4—H4 | 0.8200 |
C11—H11B | 0.9700 | C21'—N2' | 1.41 (2) |
C12—N1 | 1.460 (3) | C21'—C22' | 1.544 (16) |
C12—H12A | 0.9700 | C21'—H21C | 0.9700 |
C12—H12B | 0.9700 | C21'—H21D | 0.9700 |
C13—Cl1 | 1.789 (3) | C22'—C23' | 1.540 (14) |
C13—H13A | 0.9700 | C22'—H22C | 0.9700 |
C13—H13B | 0.9700 | C22'—H22D | 0.9700 |
C14—C19 | 1.384 (3) | C23'—O4' | 1.372 (14) |
C14—C15 | 1.385 (4) | C23'—C24' | 1.551 (15) |
C14—C26 | 1.496 (3) | C23'—H23' | 0.9800 |
C15—C16 | 1.373 (3) | C24'—C25' | 1.538 (15) |
C15—H15 | 0.9300 | C24'—H24C | 0.9700 |
C16—C17 | 1.383 (3) | C24'—H24D | 0.9700 |
C16—H16 | 0.9300 | C25'—N2' | 1.411 (19) |
C17—C18 | 1.380 (3) | C25'—H25C | 0.9700 |
C17—C20 | 1.496 (3) | C25'—H25D | 0.9700 |
C18—C19 | 1.380 (3) | O4'—H4' | 0.8200 |
C6—C1—C2 | 118.6 (2) | N2'—C20—C17 | 119.6 (8) |
C6—C1—C13 | 120.9 (2) | C14—C26—Cl2 | 110.88 (18) |
C2—C1—C13 | 120.5 (2) | C14—C26—H26A | 109.5 |
C3—C2—C1 | 120.8 (2) | Cl2—C26—H26A | 109.5 |
C3—C2—H2 | 119.6 | C14—C26—H26B | 109.5 |
C1—C2—H2 | 119.6 | Cl2—C26—H26B | 109.5 |
C2—C3—C4 | 120.3 (2) | H26A—C26—H26B | 108.1 |
C2—C3—H3 | 119.9 | C7—N1—C12 | 120.33 (19) |
C4—C3—H3 | 119.9 | C7—N1—C8 | 125.23 (19) |
C5—C4—C3 | 118.9 (2) | C12—N1—C8 | 113.28 (19) |
C5—C4—C7 | 119.0 (2) | C10—O2—H2A | 109.5 |
C3—C4—C7 | 121.8 (2) | N2—C21—C22 | 108.0 (10) |
C6—C5—C4 | 120.5 (2) | N2—C21—H21A | 110.1 |
C6—C5—H5 | 119.8 | C22—C21—H21A | 110.1 |
C4—C5—H5 | 119.8 | N2—C21—H21B | 110.1 |
C5—C6—C1 | 120.9 (2) | C22—C21—H21B | 110.1 |
C5—C6—H6 | 119.5 | H21A—C21—H21B | 108.4 |
C1—C6—H6 | 119.5 | C23—C22—C21 | 113.4 (10) |
O1—C7—N1 | 121.9 (2) | C23—C22—H22A | 108.9 |
O1—C7—C4 | 119.1 (2) | C21—C22—H22A | 108.9 |
N1—C7—C4 | 118.95 (19) | C23—C22—H22B | 108.9 |
N1—C8—C9 | 110.5 (2) | C21—C22—H22B | 108.9 |
N1—C8—H8A | 109.6 | H22A—C22—H22B | 107.7 |
C9—C8—H8A | 109.6 | O4—C23—C22 | 110.9 (6) |
N1—C8—H8B | 109.6 | O4—C23—C24 | 106.8 (7) |
C9—C8—H8B | 109.6 | C22—C23—C24 | 106.4 (10) |
H8A—C8—H8B | 108.1 | O4—C23—H23 | 110.9 |
C8—C9—C10 | 111.0 (2) | C22—C23—H23 | 110.9 |
C8—C9—H9A | 109.4 | C24—C23—H23 | 110.9 |
C10—C9—H9A | 109.4 | C25—C24—C23 | 109.3 (10) |
C8—C9—H9B | 109.4 | C25—C24—H24A | 109.8 |
C10—C9—H9B | 109.4 | C23—C24—H24A | 109.8 |
H9A—C9—H9B | 108.0 | C25—C24—H24B | 109.8 |
O2—C10—C11 | 108.6 (2) | C23—C24—H24B | 109.8 |
O2—C10—C9 | 112.8 (2) | H24A—C24—H24B | 108.3 |
C11—C10—C9 | 109.2 (2) | N2—C25—C24 | 107.6 (10) |
O2—C10—H10 | 108.7 | N2—C25—H25A | 110.2 |
C11—C10—H10 | 108.7 | C24—C25—H25A | 110.2 |
C9—C10—H10 | 108.7 | N2—C25—H25B | 110.2 |
C10—C11—C12 | 111.0 (2) | C24—C25—H25B | 110.2 |
C10—C11—H11A | 109.4 | H25A—C25—H25B | 108.5 |
C12—C11—H11A | 109.4 | C23—O4—H4 | 109.5 |
C10—C11—H11B | 109.4 | C20—N2—C25 | 119.2 (7) |
C12—C11—H11B | 109.4 | C20—N2—C21 | 122.5 (8) |
H11A—C11—H11B | 108.0 | C25—N2—C21 | 116.6 (9) |
N1—C12—C11 | 110.3 (2) | N2'—C21'—C22' | 115 (2) |
N1—C12—H12A | 109.6 | N2'—C21'—H21C | 108.5 |
C11—C12—H12A | 109.6 | C22'—C21'—H21C | 108.5 |
N1—C12—H12B | 109.6 | N2'—C21'—H21D | 108.5 |
C11—C12—H12B | 109.6 | C22'—C21'—H21D | 108.5 |
H12A—C12—H12B | 108.1 | H21C—C21'—H21D | 107.5 |
C1—C13—Cl1 | 111.73 (18) | C23'—C22'—C21' | 106 (2) |
C1—C13—H13A | 109.3 | C23'—C22'—H22C | 110.6 |
Cl1—C13—H13A | 109.3 | C21'—C22'—H22C | 110.6 |
C1—C13—H13B | 109.3 | C23'—C22'—H22D | 110.6 |
Cl1—C13—H13B | 109.3 | C21'—C22'—H22D | 110.6 |
H13A—C13—H13B | 107.9 | H22C—C22'—H22D | 108.7 |
C19—C14—C15 | 118.6 (2) | O4'—C23'—C22' | 115.4 (15) |
C19—C14—C26 | 120.4 (2) | O4'—C23'—C24' | 100.2 (15) |
C15—C14—C26 | 121.1 (2) | C22'—C23'—C24' | 113 (2) |
C16—C15—C14 | 120.8 (2) | O4'—C23'—H23' | 109.4 |
C16—C15—H15 | 119.6 | C22'—C23'—H23' | 109.4 |
C14—C15—H15 | 119.6 | C24'—C23'—H23' | 109.4 |
C15—C16—C17 | 120.6 (2) | C25'—C24'—C23' | 113 (2) |
C15—C16—H16 | 119.7 | C25'—C24'—H24C | 109.0 |
C17—C16—H16 | 119.7 | C23'—C24'—H24C | 109.0 |
C18—C17—C16 | 119.0 (2) | C25'—C24'—H24D | 109.0 |
C18—C17—C20 | 121.3 (2) | C23'—C24'—H24D | 109.0 |
C16—C17—C20 | 119.4 (2) | H24C—C24'—H24D | 107.8 |
C19—C18—C17 | 120.4 (2) | N2'—C25'—C24' | 115 (2) |
C19—C18—H18 | 119.8 | N2'—C25'—H25C | 108.5 |
C17—C18—H18 | 119.8 | C24'—C25'—H25C | 108.5 |
C18—C19—C14 | 120.7 (2) | N2'—C25'—H25D | 108.5 |
C18—C19—H19 | 119.7 | C24'—C25'—H25D | 108.5 |
C14—C19—H19 | 119.7 | H25C—C25'—H25D | 107.5 |
O3—C20—N2 | 122.4 (4) | C23'—O4'—H4' | 109.5 |
O3—C20—N2' | 121.2 (8) | C20—N2'—C21' | 129.3 (18) |
O3—C20—C17 | 118.9 (2) | C20—N2'—C25' | 122.8 (15) |
N2—C20—C17 | 118.2 (4) | C21'—N2'—C25' | 107.6 (19) |
C6—C1—C2—C3 | 1.0 (4) | C19—C14—C26—Cl2 | 101.6 (3) |
C13—C1—C2—C3 | 179.7 (2) | C15—C14—C26—Cl2 | −79.3 (3) |
C1—C2—C3—C4 | −2.1 (4) | O1—C7—N1—C12 | −3.4 (4) |
C2—C3—C4—C5 | 1.4 (4) | C4—C7—N1—C12 | 173.9 (2) |
C2—C3—C4—C7 | −172.8 (2) | O1—C7—N1—C8 | 163.5 (2) |
C3—C4—C5—C6 | 0.3 (4) | C4—C7—N1—C8 | −19.2 (4) |
C7—C4—C5—C6 | 174.6 (2) | C11—C12—N1—C7 | −135.0 (2) |
C4—C5—C6—C1 | −1.3 (4) | C11—C12—N1—C8 | 56.6 (3) |
C2—C1—C6—C5 | 0.6 (4) | C9—C8—N1—C7 | 135.6 (3) |
C13—C1—C6—C5 | −178.0 (2) | C9—C8—N1—C12 | −56.7 (3) |
C5—C4—C7—O1 | −52.0 (3) | N2—C21—C22—C23 | 52.6 (15) |
C3—C4—C7—O1 | 122.2 (3) | C21—C22—C23—O4 | −176.1 (9) |
C5—C4—C7—N1 | 130.6 (2) | C21—C22—C23—C24 | −60.4 (12) |
C3—C4—C7—N1 | −55.2 (3) | O4—C23—C24—C25 | −177.4 (8) |
N1—C8—C9—C10 | 56.2 (3) | C22—C23—C24—C25 | 64.1 (11) |
C8—C9—C10—O2 | −177.3 (2) | C23—C24—C25—N2 | −61.6 (13) |
C8—C9—C10—C11 | −56.4 (3) | O3—C20—N2—C25 | −0.8 (16) |
O2—C10—C11—C12 | 179.8 (2) | C17—C20—N2—C25 | 171.0 (9) |
C9—C10—C11—C12 | 56.4 (3) | O3—C20—N2—C21 | 163.4 (9) |
C10—C11—C12—N1 | −56.2 (3) | C17—C20—N2—C21 | −24.7 (17) |
C6—C1—C13—Cl1 | −78.8 (3) | C24—C25—N2—C20 | −138.2 (12) |
C2—C1—C13—Cl1 | 102.6 (3) | C24—C25—N2—C21 | 56.6 (15) |
C19—C14—C15—C16 | −0.1 (4) | C22—C21—N2—C20 | 144.2 (14) |
C26—C14—C15—C16 | −179.2 (2) | C22—C21—N2—C25 | −51.2 (16) |
C14—C15—C16—C17 | −1.3 (4) | N2'—C21'—C22'—C23' | 63 (3) |
C15—C16—C17—C18 | 1.3 (4) | C21'—C22'—C23'—O4' | 67 (2) |
C15—C16—C17—C20 | 174.8 (2) | C21'—C22'—C23'—C24' | −47 (2) |
C16—C17—C18—C19 | 0.1 (4) | O4'—C23'—C24'—C25' | −82 (2) |
C20—C17—C18—C19 | −173.3 (2) | C22'—C23'—C24'—C25' | 42 (2) |
C17—C18—C19—C14 | −1.5 (4) | C23'—C24'—C25'—N2' | −46 (3) |
C15—C14—C19—C18 | 1.5 (4) | O3—C20—N2'—C21' | 173 (2) |
C26—C14—C19—C18 | −179.4 (2) | C17—C20—N2'—C21' | −1 (4) |
C18—C17—C20—O3 | 118.4 (3) | O3—C20—N2'—C25' | −15 (4) |
C16—C17—C20—O3 | −55.0 (3) | C17—C20—N2'—C25' | 172 (2) |
C18—C17—C20—N2 | −53.7 (8) | C22'—C21'—N2'—C20 | 106 (3) |
C16—C17—C20—N2 | 132.9 (8) | C22'—C21'—N2'—C25' | −68 (3) |
C18—C17—C20—N2' | −67.9 (17) | C24'—C25'—N2'—C20 | −117 (3) |
C16—C17—C20—N2' | 118.7 (17) | C24'—C25'—N2'—C21' | 57 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2A···O1i | 0.82 | 2.18 | 2.789 (2) | 132 |
O4—H4···O3ii | 0.82 | 2.13 | 2.793 (3) | 138 |
C11—H11B···O3iii | 0.97 | 2.60 | 3.522 (3) | 160 |
C26—H26A···O2iv | 0.97 | 2.59 | 3.494 (4) | 154 |
Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z; (iii) −x+1, −y, −z+1; (iv) x, y+1, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2A···O1i | 0.82 | 2.18 | 2.789 (2) | 132 |
O4—H4···O3ii | 0.82 | 2.13 | 2.793 (3) | 138 |
C11—H11B···O3iii | 0.97 | 2.60 | 3.522 (3) | 160 |
C26—H26A···O2iv | 0.97 | 2.59 | 3.494 (4) | 154 |
Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z; (iii) −x+1, −y, −z+1; (iv) x, y+1, z. |
Acknowledgements
The authors thank the DST–FIST, Central Instrumentation Facility, Queen Mary's College, Chennai-4, for the computing facility and the SAIF, IIT, Madras, for the X-ray data-collection facility.
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Many piperidine containing compounds possess remarkable biological and medicinal properties (Daly et al., (1986); Fodor et al., (1985)). Among their remarkable properties, they show appreciable effect on plasma glucose level (Campfield et al., (1995)), insulin normalization, therapeutics on cocaine abuse (Kozikowski et al., (1998)). Piperidine also participates in amny local anesthetics, such as mepivacaine, ropivacaine, and bupivacaine, extensively used in clinical practice (Brau et al., (2000); Bolzani et al., (1995)). Piperidine derivatives are found to exhibit pharmacological activity and form a vital part of the molecular structures of important drugs such as raloxifene and minoxidil. Selective inhibition of a number of enzymes has rendered piperidine alkaloids as important paraphernalia in the study of biochemical pathways (Gulluoglu et al., (2007).
The title compound, C13H16ClNO2, (I), crystallizes with two molecules in the asymmetric unit: A ( Fig1, left) and B (Fig 1, right) . Bond lengths and angles are comparable with literature values. C—N distances of the piperdine ring in molecule A C8—C12/N1 & in molecule B C21—C25/N2, are in the range 1.459 (3)- 1.462 (3) Å and are in good agreement with values of a similar reported structure (Revathi et al., (2015)). The C=O distances in molecules A & B are [1.235 (3) and 1.233 (3) Å], respectively, and is comparable with the previously reported value(Prathebha et al., (2015). In the molecule A, the dihedral angle between piperdine ring and the phenyl ring 47.22 (1)°, indicates the bisectional orientation of the phenylring. The bond angles around the N1 and N2 atoms [358.85 (2)° and 359.47 (2)°, respectively], shows sp2 hybridization of the atoms. The piperidine ring of the molecule A, adopts a chair conformation with puckering parameters of q2 = 0.019 (2) Å, φ2 = -58.74° q3 = -0.567 (3) Å, QT= 0.567 (3) Å and θ2 = 178.03 (2)°.
In the crystal packing the molecules form chains running along the diagonal of 'bc' plane through O—H···O type hydrogen bonds. These chains are further inter linked through C—H···O type hydrogen bonds to form molecular ribbons (Fig. 2).