(3-Hy­droxy­piperidin-1-yl)(4-methyl­phen­yl)methanone

Gomathi, S.; Reuben Jonathan, D.; Mohamooda Sumaya, U.; Dravida Thendral, E.R.A.; Usha, G.

doi:10.1107/S2414314617014936

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 2| Part 10| October 2017| x171493

https://doi.org/10.1107/S2414314617014936

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(3-Hydroxypiperidin-1-yl)(4-methylphenyl)methanone

S. Gomathi,^a D. Reuben Jonathan,^b U. Mohamooda Sumaya,^c E. R. A. Dravida Thendral ^d and G. Usha ^d ^*

^aDepartment of Physics, Bhaktavatsalam Memorial College for Women, Korattur, Chennai-80, Tamilnadu, India, ^bDepartment of Chemistry, Madras Christian College, Chennai-59, India, ^cDepartment of Physics, Bharathi Women's College, Chennai 600 108, Tamilnadu, India, and ^dPG and Research Department of Physics, Queen Mary's College, Chennai-4, Tamilnadu, India
^*Correspondence e-mail: guqmc@yahoo.com

Edited by P. C. Healy, Griffith University, Australia (Received 26 August 2017; accepted 14 October 2017; online 27 October 2017)

In the title molecule, C₁₃H₁₇NO₂, the piperidine ring assumes a chair conformation. The dihedral angle between the mean plane of the piperidine ring and the benzene ring is 45.49 (1)°. In the crystal, molecules are linked by O—H⋯O intermolecular hydrogen bonds, leading to a molecular chain running along the c-axis direction. The atoms of the hydroxy piperidine ring and the methyl group of methylphenyl ring are disordered over two sets of sites with refined occupancies of 0.754 (5) and 0.246 (5).

Keywords: crystal structure; piperidine; hydrogen bonds.

CCDC reference: 1580031

Structure description

Piperidine and its derivative have played vital roles in the design of pharmaceutical drugs (Das & Brahmachari, 2013 ). It has been shown that the antioxidant activity of the title molecule can be enhanced by the substitution of hydroxyl, methoxy, nitro and alkyl groups on the piperidine ring system (Ravindernath & Reddy, 2017 ).

In the compound (Fig. 1), the bond lengths are typical of such derivatives and are in good agreement with literature values (Allen et al., 1987 ). The C—N distances [1.370 (5)–1.464 (5) Å], C=O distance [1.189 (5) Å] and C—O distance [1.399 (5) Å] are in good agreement with the values of similar reported structures (Revathi et al., 2015 ; Prathebha et al., 2015 ). The +syn-periplanar(+sp) orientation of the keto group with the hydroxypiperidine ring is revealed by the torsion angle O1—C8—N1—C9 [15.1 (6)]°. The total angle (359.5°) around the N atom indicates sp² hybridization of this atom. The piperidine ring (N1/C9–C13) adopts a chair conformation with puckering parameters q2 = 0.0097 (4), q3 = 0.5605 (4), Q_T= 0.5605 (4) Å, φ2 = −22 (21)° and θ2 = 1.0 (4)°. Atoms C10 and C13 deviate by −0.233 (2) and 0.243 (2) Å, respectively, from the mean plane through all ring atoms.

Figure 1
ORTEP-3 for Windows (Farrugia, 2012

) plot of the title compound, with displacement ellipsoids drawn at the 30% probability level.

In the crystal, molecules are linked through O—H⋯O hydrogen bonds (Table 1, Fig. 2), forming chains running parallel to [001].

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9B⋯O1ⁱ	0.97	2.66	3.598 (7)	163
O2—H2⋯O1ⁱⁱ	0.82	2.02	2.802 (7)	159
O2′—H2′⋯O1′ⁱⁱ	0.82	2.07	2.70 (3)	134
Symmetry codes: (i) $[-x, -y, z-{\script{1\over 2}}]$ ; (ii) x, y, z-1.

Figure 2
The crystal packing of the title compound, viewed along the b axis with hydrogen bonds indicated by dashed lines.

Synthesis and crystallization

The title compound was synthesized following a published procedure (Revathi et al., 2015 ). In a 250 ml round-bottomed flask, 15 ml of ethyl methyl ketone was added to 3-hydroxy piperidine (0.01 mol; 1 g m) and stirred at room temperature. After 5 min, triethylamine (0.02 mol; 1.3 ml) was added and the mixture stirred for 15 min. Then 4-methyl benzoyl chloride (0.02 mol; 1.2 ml) and 15 ml of ethyl methyl ketone were added and the reaction mixture stirred at room temperature for 2 h. A white precipitate was formed which was filtered off. The filtrate was evaporated to give the crude product. It was then recrystallized twice from ethyl methyl ketone to give yellow block-like crystals of the title compound (m.p. 70°C, yield 82%).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The atoms of the hydroxy piperidine ring and the methyl group of methylphenyl ring are disordered over two sets of sites with refined occupancies of 0.754 (5) and 0.246 (5).

Table 2
Experimental details

Crystal data
Chemical formula	C₁₃H₁₇NO₂
M_r	219.28
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	293
a, b, c (Å)	24.8766 (14), 6.1117 (4), 7.9388 (4)
V (Å³)	1207.00 (12)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.08
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2004 )
T_min, T_max	0.976, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	20282, 2385, 1692
R_int	0.055
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.099, 1.11
No. of reflections	2385
No. of parameters	230
No. of restraints	99
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.13, −0.11
Absolute structure	Flack x determined using 675 quotients [(I⁺)−(I⁻)]/[(I⁺)+(I⁻)] (Parsons et al, 2013 )
Absolute structure parameter	0.3 (5)
Computer programs: APEX2, SAINT and XPREP (Bruker, 2004), SHELXS97 and SHELXL97 (Sheldrick, 2008 ) and ORTEP-3 for Windows (Farrugia, 2012 ).

Structural data

CCDC reference: 1580031

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: https://doi.org/10.1107/S2414314617014936/hg4026sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617014936/hg4026Isup3.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314617014936/hg4026Isup3.cml

checkCIF report

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: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

(3-Hydroxypiperidin-1-yl)(4-methylphenyl)methanone top

Crystal data top

C₁₃H₁₇NO₂	F(000) = 472
M_r = 219.28	D_x = 1.207 Mg m⁻³
Orthorhombic, Pca2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 2385 reflections
a = 24.8766 (14) Å	θ = 0.8–0.7°
b = 6.1117 (4) Å	µ = 0.08 mm⁻¹
c = 7.9388 (4) Å	T = 293 K
V = 1207.00 (12) Å³	Block, yellow
Z = 4	0.30 × 0.25 × 0.20 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	2385 independent reflections
Radiation source: fine-focus sealed tube	1692 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.055
ω and \ f scan	θ_max = 26.0°, θ_min = 3.3°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −30→30
T_min = 0.976, T_max = 0.984	k = −7→7
20282 measured reflections	l = −9→9

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.039	w = 1/[σ²(F_o²) + (0.0468P)² + 0.0531P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.099	(Δ/σ)_max < 0.001
S = 1.11	Δρ_max = 0.13 e Å⁻³
2385 reflections	Δρ_min = −0.11 e Å⁻³
230 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
99 restraints	Extinction coefficient: 0.141 (11)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack x determined using 675 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al. (2013)
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.3 (5)

Special details top

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

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) 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.

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 of 0.82 Å with U_iso(H)= 1.5 U_eq(c-methyl),and U_iso(H)= 1.2Ueq(C) for other H atoms.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
C3	0.18222 (11)	−0.4020 (4)	1.0752 (3)	0.0762 (7)
H3	0.1791	−0.5388	1.1256	0.091*
C4	0.13647 (8)	−0.2764 (3)	1.0519 (3)	0.0670 (6)
H4	0.1032	−0.3274	1.0885	0.080*
C5	0.14041 (8)	−0.0763 (3)	0.9743 (2)	0.0576 (5)
C6	0.19040 (9)	−0.0040 (4)	0.9234 (3)	0.0701 (6)
H6	0.1935	0.1314	0.8708	0.084*
C7	0.23570 (8)	−0.1285 (4)	0.9492 (3)	0.0748 (6)
H7	0.2690	−0.0765	0.9145	0.090*
C8	0.09139 (9)	0.0653 (3)	0.9589 (3)	0.0666 (6)
C2	0.23190 (9)	−0.3301 (4)	1.0261 (3)	0.0733 (7)
C1	0.2817 (3)	−0.4667 (13)	1.0622 (13)	0.116 (3)	0.754 (5)
H1A	0.3073	−0.4472	0.9729	0.174*	0.754 (5)
H1B	0.2719	−0.6183	1.0694	0.174*	0.754 (5)
H1C	0.2974	−0.4208	1.1669	0.174*	0.754 (5)
C9	0.02203 (13)	0.2386 (6)	0.7818 (4)	0.0590 (8)	0.754 (5)
H9A	0.0114	0.2993	0.8897	0.071*	0.754 (5)
H9B	−0.0085	0.1612	0.7347	0.071*	0.754 (5)
C10	0.03892 (17)	0.4199 (6)	0.6648 (5)	0.0643 (10)	0.754 (5)
H10A	0.0666	0.5071	0.7187	0.077*	0.754 (5)
H10B	0.0084	0.5144	0.6428	0.077*	0.754 (5)
C11	0.06016 (18)	0.3312 (8)	0.4998 (5)	0.0669 (12)	0.754 (5)
H11A	0.0312	0.2601	0.4389	0.080*	0.754 (5)
H11B	0.0734	0.4511	0.4313	0.080*	0.754 (5)
C12	0.10493 (16)	0.1694 (7)	0.5298 (4)	0.0621 (9)	0.754 (5)
H12	0.1339	0.2492	0.5867	0.075*	0.754 (5)
C13	0.08638 (13)	−0.0078 (5)	0.6499 (3)	0.0529 (8)	0.754 (5)
H13A	0.0579	−0.0923	0.5978	0.063*	0.754 (5)
H13B	0.1160	−0.1060	0.6740	0.063*	0.754 (5)
N1	0.06702 (11)	0.0872 (5)	0.8051 (3)	0.0498 (7)	0.754 (5)
O1	0.0701 (2)	0.1339 (12)	1.0822 (7)	0.0802 (15)	0.754 (5)
O2	0.12710 (16)	0.0789 (9)	0.3835 (4)	0.1091 (16)	0.754 (5)
H2	0.1118	0.1294	0.3007	0.164*	0.754 (5)
C1'	0.2820 (6)	−0.480 (4)	1.037 (3)	0.095 (7)	0.246 (5)
H1'1	0.3139	−0.3949	1.0188	0.142*	0.246 (5)
H1'2	0.2796	−0.5919	0.9519	0.142*	0.246 (5)
H1'3	0.2835	−0.5473	1.1460	0.142*	0.246 (5)
C9'	0.0545 (5)	0.363 (2)	0.7878 (13)	0.081 (4)	0.246 (5)
H9'1	0.0743	0.4953	0.7602	0.097*	0.246 (5)
H9'2	0.0362	0.3883	0.8940	0.097*	0.246 (5)
C10'	0.0136 (5)	0.325 (3)	0.6554 (15)	0.081 (4)	0.246 (5)
H10C	−0.0066	0.4583	0.6364	0.097*	0.246 (5)
H10D	−0.0114	0.2131	0.6933	0.097*	0.246 (5)
C11'	0.0396 (6)	0.251 (3)	0.4900 (19)	0.087 (5)	0.246 (5)
H11C	0.0121	0.2065	0.4106	0.104*	0.246 (5)
H11D	0.0596	0.3717	0.4407	0.104*	0.246 (5)
C12'	0.0770 (6)	0.062 (2)	0.5267 (15)	0.083 (4)	0.246 (5)
H12'	0.0547	−0.0547	0.5744	0.100*	0.246 (5)
C13'	0.1182 (4)	0.1118 (19)	0.6524 (12)	0.071 (3)	0.246 (5)
H13C	0.1417	0.2262	0.6103	0.085*	0.246 (5)
H13D	0.1398	−0.0174	0.6734	0.085*	0.246 (5)
N1'	0.0927 (4)	0.1837 (17)	0.8095 (9)	0.064 (3)	0.246 (5)
O1'	0.0737 (10)	0.179 (4)	1.098 (3)	0.110 (8)	0.246 (5)
O2'	0.1012 (5)	−0.0230 (18)	0.3875 (13)	0.084 (3)	0.246 (5)
H2'	0.0802	−0.0193	0.3079	0.126*	0.246 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C3	0.1035 (19)	0.0606 (13)	0.0644 (13)	0.0231 (12)	−0.0065 (13)	0.0065 (11)
C4	0.0729 (13)	0.0679 (14)	0.0601 (12)	0.0152 (10)	0.0062 (10)	0.0074 (10)
C5	0.0705 (13)	0.0611 (12)	0.0413 (9)	0.0178 (10)	0.0010 (9)	0.0032 (9)
C6	0.0805 (14)	0.0612 (11)	0.0686 (14)	0.0120 (11)	0.0052 (11)	0.0074 (10)
C7	0.0665 (13)	0.0795 (16)	0.0784 (14)	0.0045 (12)	−0.0032 (12)	−0.0057 (12)
C8	0.0769 (13)	0.0750 (14)	0.0477 (11)	0.0262 (11)	0.0040 (11)	0.0086 (10)
C2	0.0765 (16)	0.0815 (16)	0.0618 (14)	0.0287 (13)	−0.0157 (11)	−0.0186 (12)
C1	0.126 (6)	0.120 (6)	0.100 (5)	0.078 (5)	−0.028 (3)	−0.044 (4)
C9	0.0543 (17)	0.071 (2)	0.0519 (17)	0.0210 (15)	0.0023 (13)	0.0046 (14)
C10	0.075 (2)	0.059 (2)	0.059 (2)	0.0239 (16)	−0.0076 (18)	0.0038 (17)
C11	0.075 (3)	0.080 (2)	0.0464 (19)	0.0186 (19)	−0.0010 (17)	0.0135 (17)
C12	0.062 (2)	0.086 (2)	0.0380 (16)	0.0183 (17)	0.0000 (13)	0.0011 (16)
C13	0.0557 (16)	0.0535 (17)	0.0494 (16)	0.0130 (14)	−0.0132 (12)	−0.0121 (13)
N1	0.0508 (15)	0.0529 (15)	0.0457 (12)	0.0118 (12)	−0.0007 (11)	0.0038 (11)
O1	0.082 (2)	0.119 (4)	0.040 (2)	0.046 (2)	0.0107 (16)	0.002 (2)
O2	0.096 (3)	0.186 (5)	0.0448 (12)	0.071 (3)	0.0066 (16)	−0.003 (2)
C1'	0.041 (8)	0.153 (18)	0.090 (12)	0.015 (7)	−0.032 (7)	0.037 (11)
C9'	0.097 (8)	0.083 (7)	0.062 (6)	0.046 (6)	−0.020 (5)	−0.015 (5)
C10'	0.077 (8)	0.108 (9)	0.058 (6)	0.033 (6)	−0.016 (6)	−0.015 (7)
C11'	0.092 (9)	0.108 (10)	0.060 (6)	0.050 (8)	−0.019 (6)	−0.009 (7)
C12'	0.096 (8)	0.093 (8)	0.062 (6)	0.043 (7)	−0.019 (6)	−0.019 (6)
C13'	0.079 (7)	0.069 (6)	0.064 (6)	0.016 (6)	0.007 (5)	0.000 (5)
N1'	0.075 (6)	0.076 (6)	0.040 (4)	0.028 (5)	−0.014 (4)	−0.015 (4)
O1'	0.188 (15)	0.085 (8)	0.057 (8)	0.075 (8)	−0.027 (7)	−0.036 (6)
O2'	0.100 (8)	0.097 (7)	0.054 (4)	0.045 (5)	−0.003 (5)	−0.024 (4)

Geometric parameters (Å, º) top

C3—C2	1.368 (3)	C11—H11B	0.9700
C3—C4	1.385 (3)	C12—O2	1.399 (5)
C3—H3	0.9300	C12—C13	1.515 (5)
C4—C5	1.373 (3)	C12—H12	0.9800
C4—H4	0.9300	C13—N1	1.444 (3)
C5—C6	1.380 (3)	C13—H13A	0.9700
C5—C8	1.500 (3)	C13—H13B	0.9700
C6—C7	1.375 (3)	O2—H2	0.8200
C6—H6	0.9300	C1'—H1'1	0.9600
C7—C2	1.379 (3)	C1'—H1'2	0.9600
C7—H7	0.9300	C1'—H1'3	0.9600
C8—O1	1.189 (5)	C9'—N1'	1.463 (11)
C8—N1	1.370 (3)	C9'—C10'	1.481 (14)
C8—O1'	1.37 (2)	C9'—H9'1	0.9700
C8—N1'	1.390 (9)	C9'—H9'2	0.9700
C2—C1	1.522 (5)	C10'—C11'	1.531 (15)
C2—C1'	1.551 (13)	C10'—H10C	0.9700
C1—H1A	0.9600	C10'—H10D	0.9700
C1—H1B	0.9600	C11'—C12'	1.512 (14)
C1—H1C	0.9600	C11'—H11C	0.9700
C9—N1	1.464 (3)	C11'—H11D	0.9700
C9—C10	1.506 (5)	C12'—O2'	1.362 (15)
C9—H9A	0.9700	C12'—C13'	1.463 (14)
C9—H9B	0.9700	C12'—H12'	0.9800
C10—C11	1.513 (5)	C13'—N1'	1.467 (11)
C10—H10A	0.9700	C13'—H13C	0.9700
C10—H10B	0.9700	C13'—H13D	0.9700
C11—C12	1.508 (5)	O2'—H2'	0.8200
C11—H11A	0.9700

C2—C3—C4	121.7 (2)	C11—C12—C13	110.1 (3)
C2—C3—H3	119.1	O2—C12—H12	106.8
C4—C3—H3	119.1	C11—C12—H12	106.8
C5—C4—C3	119.7 (2)	C13—C12—H12	106.8
C5—C4—H4	120.2	N1—C13—C12	110.6 (3)
C3—C4—H4	120.2	N1—C13—H13A	109.5
C4—C5—C6	118.73 (18)	C12—C13—H13A	109.5
C4—C5—C8	119.50 (18)	N1—C13—H13B	109.5
C6—C5—C8	121.60 (18)	C12—C13—H13B	109.5
C7—C6—C5	121.2 (2)	H13A—C13—H13B	108.1
C7—C6—H6	119.4	C8—N1—C13	125.0 (2)
C5—C6—H6	119.4	C8—N1—C9	120.8 (2)
C6—C7—C2	120.3 (2)	C13—N1—C9	113.7 (2)
C6—C7—H7	119.9	C12—O2—H2	109.5
C2—C7—H7	119.9	C2—C1'—H1'1	109.5
O1—C8—N1	120.1 (3)	C2—C1'—H1'2	109.5
O1—C8—O1'	11.4 (14)	H1'1—C1'—H1'2	109.5
N1—C8—O1'	121.5 (11)	C2—C1'—H1'3	109.5
O1—C8—N1'	121.9 (5)	H1'1—C1'—H1'3	109.5
N1—C8—N1'	36.8 (4)	H1'2—C1'—H1'3	109.5
O1'—C8—N1'	115.3 (11)	N1'—C9'—C10'	114.2 (9)
O1—C8—C5	119.9 (3)	N1'—C9'—H9'1	108.7
N1—C8—C5	119.25 (19)	C10'—C9'—H9'1	108.7
O1'—C8—C5	119.2 (11)	N1'—C9'—H9'2	108.7
N1'—C8—C5	110.5 (4)	C10'—C9'—H9'2	108.7
C3—C2—C7	118.40 (19)	H9'1—C9'—H9'2	107.6
C3—C2—C1	120.4 (5)	C9'—C10'—C11'	111.4 (10)
C7—C2—C1	121.2 (5)	C9'—C10'—H10C	109.3
C3—C2—C1'	121.3 (9)	C11'—C10'—H10C	109.3
C7—C2—C1'	119.9 (9)	C9'—C10'—H10D	109.3
C1—C2—C1'	8.1 (13)	C11'—C10'—H10D	109.3
C2—C1—H1A	109.5	H10C—C10'—H10D	108.0
C2—C1—H1B	109.5	C12'—C11'—C10'	108.5 (11)
C2—C1—H1C	109.5	C12'—C11'—H11C	110.0
N1—C9—C10	109.2 (2)	C10'—C11'—H11C	110.0
N1—C9—H9A	109.8	C12'—C11'—H11D	110.0
C10—C9—H9A	109.8	C10'—C11'—H11D	110.0
N1—C9—H9B	109.8	H11C—C11'—H11D	108.4
C10—C9—H9B	109.8	O2'—C12'—C13'	108.8 (10)
H9A—C9—H9B	108.3	O2'—C12'—C11'	114.1 (11)
C9—C10—C11	111.6 (3)	C13'—C12'—C11'	113.8 (11)
C9—C10—H10A	109.3	O2'—C12'—H12'	106.5
C11—C10—H10A	109.3	C13'—C12'—H12'	106.5
C9—C10—H10B	109.3	C11'—C12'—H12'	106.5
C11—C10—H10B	109.3	C12'—C13'—N1'	109.8 (8)
H10A—C10—H10B	108.0	C12'—C13'—H13C	109.7
C12—C11—C10	110.9 (3)	N1'—C13'—H13C	109.7
C12—C11—H11A	109.5	C12'—C13'—H13D	109.7
C10—C11—H11A	109.5	N1'—C13'—H13D	109.7
C12—C11—H11B	109.5	H13C—C13'—H13D	108.2
C10—C11—H11B	109.5	C8—N1'—C9'	118.4 (8)
H11A—C11—H11B	108.1	C8—N1'—C13'	125.4 (7)
O2—C12—C11	114.8 (3)	C9'—N1'—C13'	114.0 (8)
O2—C12—C13	111.1 (3)	C12'—O2'—H2'	109.5

C2—C3—C4—C5	1.4 (3)	N1'—C8—N1—C13	82.2 (6)
C3—C4—C5—C6	−0.9 (3)	C5—C8—N1—C13	−3.4 (4)
C3—C4—C5—C8	−176.20 (19)	O1—C8—N1—C9	15.1 (6)
C4—C5—C6—C7	0.0 (3)	O1'—C8—N1—C9	1.9 (13)
C8—C5—C6—C7	175.2 (2)	N1'—C8—N1—C9	−89.1 (6)
C5—C6—C7—C2	0.3 (3)	C5—C8—N1—C9	−174.6 (2)
C4—C5—C8—O1	63.9 (5)	C12—C13—N1—C8	−112.6 (4)
C6—C5—C8—O1	−111.3 (5)	C12—C13—N1—C9	59.2 (4)
C4—C5—C8—N1	−106.4 (3)	C10—C9—N1—C8	114.0 (4)
C6—C5—C8—N1	78.4 (3)	C10—C9—N1—C13	−58.2 (4)
C4—C5—C8—O1'	77.0 (13)	N1'—C9'—C10'—C11'	−50.2 (19)
C6—C5—C8—O1'	−98.2 (12)	C9'—C10'—C11'—C12'	51.2 (19)
C4—C5—C8—N1'	−146.0 (5)	C10'—C11'—C12'—O2'	177.8 (13)
C6—C5—C8—N1'	38.8 (6)	C10'—C11'—C12'—C13'	−56.6 (19)
C4—C3—C2—C7	−1.1 (3)	O2'—C12'—C13'—N1'	−174.5 (10)
C4—C3—C2—C1	176.7 (4)	C11'—C12'—C13'—N1'	57.1 (17)
C4—C3—C2—C1'	−174.0 (12)	O1—C8—N1'—C9'	−18.1 (12)
C6—C7—C2—C3	0.2 (3)	N1—C8—N1'—C9'	80.7 (10)
C6—C7—C2—C1	−177.6 (4)	O1'—C8—N1'—C9'	−28.7 (16)
C6—C7—C2—C1'	173.2 (12)	C5—C8—N1'—C9'	−167.5 (8)
N1—C9—C10—C11	54.8 (5)	O1—C8—N1'—C13'	179.8 (9)
C9—C10—C11—C12	−54.5 (5)	N1—C8—N1'—C13'	−81.4 (10)
C10—C11—C12—O2	−179.9 (4)	O1'—C8—N1'—C13'	169.2 (14)
C10—C11—C12—C13	53.9 (5)	C5—C8—N1'—C13'	30.3 (12)
O2—C12—C13—N1	176.0 (3)	C10'—C9'—N1'—C8	−112.8 (14)
C11—C12—C13—N1	−55.7 (4)	C10'—C9'—N1'—C13'	51.3 (17)
O1—C8—N1—C13	−173.6 (5)	C12'—C13'—N1'—C8	109.9 (14)
O1'—C8—N1—C13	173.2 (13)	C12'—C13'—N1'—C9'	−52.9 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9B···O1ⁱ	0.97	2.66	3.598 (7)	163
O2—H2···O1ⁱⁱ	0.82	2.02	2.802 (7)	159
O2′—H2′···O1′ⁱⁱ	0.82	2.07	2.70 (3)	134

Symmetry codes: (i) −x, −y, z−1/2; (ii) x, y, z−1.

Acknowledgements

The authors thank the Central Instrumentation Facility, Queen Mary's College, Chennai-4 for computing facility and the SAIF, IIT, Madras, for the X-ray data collection facility.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CSD CrossRef Web of Science Google Scholar
Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Das, S. & Brahmachari, G. (2013). J. Org. Biomol. Chem. 1, 33–46. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Parsons, S., Flack, H. D. & Wagner, T. (2013). Acta Cryst. B69, 249–259. Web of Science CrossRef CAS IUCr Journals Google Scholar
Prathebha, K., Reuben Jonathan, D., Revathi, B. K., Sathya, S. & Usha, G. (2015). Acta Cryst. E71, o39–o40. Web of Science CSD CrossRef IUCr Journals Google Scholar
Ravindernath, A. & Reddy, M. S. (2017). Arabian J. Chem. 10, s1172–s1179. Web of Science CrossRef CAS Google Scholar
Revathi, B. K., Reuben Jonathan, D., Kalai Sevi, K., Dhanalakshmi, K. & Usha, G. (2015). Acta Cryst. E71, o817–o818. CrossRef IUCr Journals Google Scholar
Revathi, B. K., Reuben Jonathan, D., Sathya, S., Prathebha, K. & Usha, G. (2015). Acta Cryst. E71, o359–o360. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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