Crystal structure of [4-(chloro­meth­yl)phen­yl](4-hy­droxy­piperidin-1-yl)methanone

Revathi, B.K.; Reuben Jonathan, D.; Kalai Sevi, K.; Dhanalakshmi, K.; Usha, G.

doi:10.1107/S2056989015016096

organic compounds

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ISSN: 2056-9890

Volume 71| Part 10| October 2015| Pages o703-o704

doi:10.1107/S2056989015016096

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Crystal structure of [4-(chloromethyl)phenyl](4-hydroxypiperidin-1-yl)methanone

B. K. Revathi,^a D. Reuben Jonathan,^b K. Kalai Sevi,^c K. Dhanalakshmi ^d and G. Usha ^a ^*

^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

Edited by R. F. Baggio, Comisión Nacional de Energía Atómica, Argentina (Received 26 August 2015; accepted 28 August 2015; online 12 September 2015)

The title compound, C₁₃H₁₆ClNO₂, crystallized with two independent molecules in the asymmetric unit (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

C₁₃H₁₆ClNO₂
M_r = 253.72
Triclinic, $[P \overline 1]$
a = 8.4131 (3) Å
b = 9.6211 (4) Å
c = 15.6780 (6) Å
α = 80.917 (3)°
β = 89.240 (2)°
γ = 88.395 (2)°
V = 1252.57 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 293 K
0.35 × 0.30 × 0.25 mm

2.2. Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.902, T_max = 0.943
28447 measured reflections
4415 independent reflections
3411 reflections with I > 2σ(I)
R_int = 0.027

2.3. Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.128
S = 1.05
4415 reflections
371 parameters
111 restraints
H-atom parameters constrained
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.62 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

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⋯O2^iv	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.

Data collection: APEX2 (Bruker, 2004); cell refinement: 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

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S2056989015016096/bg2567sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989015016096/bg2567Isup2.hkl

Supporting information file. DOI: 10.1107/S2056989015016096/bg2567Isup3.cml

checkCIF report

Comment top

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).

Related literature top

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).

Experimental top

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.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: 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).

Figures top

	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.

[4-(Chloromethyl)phenyl](4-hydroxypiperidin-1-yl)methanone top

Crystal data top

C₁₃H₁₆ClNO₂	Z = 4
M_r = 253.72	F(000) = 536
Triclinic, P1	D_x = 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

Data collection top

Bruker Kappa APEXII CCD diffractometer	4415 independent reflections
Radiation source: fine-focus sealed tube	3411 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ω and φ scan	θ_max = 25.0°, θ_min = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −10→10
T_min = 0.902, T_max = 0.943	k = −11→11
28447 measured reflections	l = −18→18

Refinement top

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(F_o²) + (0.0477P)² + 1.0906P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
4415 reflections	Δρ_max = 0.45 e Å⁻³
371 parameters	Δρ_min = −0.61 e Å⁻³

Crystal data top

C₁₃H₁₆ClNO₂	γ = 88.395 (2)°
M_r = 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)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	4415 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	3411 reflections with I > 2σ(I)
T_min = 0.902, T_max = 0.943	R_int = 0.027
28447 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	111 restraints
wR(F²) = 0.128	H-atom parameters constrained
S = 1.05	Δρ_max = 0.45 e Å⁻³
4415 reflections	Δρ_min = −0.61 e Å⁻³
371 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq	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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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···O2^iv	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.

Hydrogen-bond geometry (Å, º) top

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···O2^iv	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.

References

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Volume 71| Part 10| October 2015| Pages o703-o704

doi:10.1107/S2056989015016096

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystal structure of [4-(chloro­meth­yl)phen­yl](4-hy­dr­oxy­piperidin-1-yl)methanone

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of [4-(chloromethyl)phenyl](4-hydroxypiperidin-1-yl)methanone