5-(2-Hy­droxy-5-meth­oxy­benzo­yl)-1-methyl-3-nitro­pyridin-2(1H)-one

Bargavi, S.; Nataraj, P.; Perumal, P.T.; Lakshmi, S.

doi:10.1107/S2414314616012359

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 1| Part 8| August 2016| x161235

doi:10.1107/S2414314616012359

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5-(2-Hydroxy-5-methoxybenzoyl)-1-methyl-3-nitropyridin-2(1H)-one

Srinivasan Bargavi,^a Poomathi Nataraj,^b Paramasivam T. Perumal ^b and Srinivasakannan Lakshmi ^a ^*

^aResearch Department of Physics, S.D.N.B. Vaishnav College for Women, Chromepet, Chennai 600 044, India, and ^bOrganic Chemistry Division, CSIR Central Leather Research Institute, Chennai 600 020, India
^*Correspondence e-mail: lakssdnbvc@gmail.com

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 18 July 2016; accepted 30 July 2016; online 12 August 2016)

In the title compound, C₁₄H₁₂N₂O₆, the dihedral angle between the benzene and pyridine rings is 65.90 (7)°. The nitro group is disordered and tilted with respect to the mean plane of the pyridine ring by 21.5 (4) and 22.8 (5)°, for the major and minor components, respectively. In the crystal, molecules are linked by O—H⋯N hydrogen bonds, forming chains propagating along [10-1]. The chains are linked by C—H⋯O hydrogen bonds, forming a three-dimensional framework. The crystal packing is further stabilized by offset π–π stacking interactions [intercentroid distance = 3.6291 (9) Å]

Keywords: crystal structure; nitropyridine; hydrogen bonding; framework; offset π–π interactions.

CCDC reference: 1063585

Structure description

The pyridine skeleton is of great importance in clinically useful molecules having diverse biological activities (Patoliya et al., 2015 ). Pyridine derivatives possess analgesic (Ajitkumar & Pandeya, 2011 ), anticancer (Hammam et al., 2001 ), antimicrobial and anti-oxidative (Prachayasittikul et al., 2008 ) activities. Pyridoxine, a derivative of pyridine, is an active neutraceutical found in the form of vitamin B3 (Chaubey et al., 2011 ). Pyridine fused-ring systems act as chemotherapeutic agents (Kumar et al., 2011 ). Picryl amino pyridines and their N-oxides possess antibacterial and antifungal (Badgujar et al., 2010 ) activities. Pyridine congeners are associated with pesticidal, insecticidal and fungicidal properties (Pradhan et al., 2012 ). As part of our studies in this area, we describe herein the synthesis and crystal structure of the title nitropyridine derivative.

In the title compound, Fig. 1, the dihedral angle between the benzene (C1–C6) and pyridine (N1/C8–C12) rings is 65.90 (7)°. Atom O6 of the nitro group is disordered, and the NO₂ groups are tilted with respect to the mean plane of the pyridine ring by 21.5 (4) and 22.8 (5)°, for the major (N2/O5/O6A) and minor (N2/O5/O6B) components, respectively. The methyl carbon atom C13 deviates from the plane of the pyridine ring by 0.070 (2) Å. The C14—O2—C2—C3 torsion angle of 178.54 (15)° indicates that the methoxy group (–O2—C14) is not quite coplanar with the phenol ring.

Figure 1
The molecular structure of the title compound, showing the atom labelling. Displacement ellipsoids are drawn at the 50% probability level.

In the crystal, molecules are linked by O—H⋯N hydrogen bonds, forming chains propagating along [10 $[\overline{1}]$ ]; see Fig. 2 and Table 1. The chains are linked by C—H⋯O hydrogen bonds forming a three-dimensional framework (Table 1 and Fig. 3). The crystal packing also features offset π–π stacking interactions [Cg1⋯Cg2ⁱⁱⁱ = 3.6291 (9) Å, interplanar distance = 3.4403 (6) Å, slippage = 1.111 Å, Cg1 and Cg2 are the centroids of rings N1/C8—C12 and C1—C6, respectively, symmetry code: (iii) −x + $[{1\over 2}]$ , y − $[{1\over 2}]$ , −z + $[{1\over 2}]$ ]

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯O4ⁱ	0.83 (2)	1.87 (2)	2.6948 (17)	173 (2)
C4—H4⋯O4ⁱ	0.93	2.56	3.233 (2)	129
C14—H14B⋯O3ⁱⁱ	0.96	2.41	3.319 (2)	158
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Figure 2
A partial view along the b axis of the crystal packing of the title compound. Hydrogen bonds are shown as dashed lines (see Table 1

Figure 3
A view along the a axis of the crystal packing of the title compound. Hydrogen bonds are shown as dashed lines (see Table 1

) and, for clarity, only the H atoms involved in hydrogen bonding are shown.

Synthesis and crystallization

A mixture of 6-methoxy-3-formylchromone (1 mmol), (Z)-N-methyl-1-(methylthio)-2-nitroethenamine (1 mmol), and indium trifluoromethanesulfonate (0.020 mmol) in ethanol (3 ml) were heated at reflux, and the resulting solution was stirred for 1 h. The consumption of the starting material was monitored by TLC. After completion of the reaction, the compound obtained was purified by column chromatography to obtain pure product in good yield (78%). The purified compound was recrystallized from the mixed solvents of ethanol and DMSO-D₆. On slow evaporation of the solvents, block-like colourless crystals of the title compound were obtained.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. Atom O6 of the NO₂ group was split over two positions and refined with a fixed occupancy ratio of O6A:O6B = 0.6:0.4.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₄H₁₂N₂O₆
M_r	304.26
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	12.5891 (4), 7.7739 (2), 14.1240 (4)
β (°)	100.466 (1)
V (Å³)	1359.27 (7)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.12
Crystal size (mm)	0.30 × 0.25 × 0.25

Data collection
Diffractometer	Bruker Kappa APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2008 )
T_min, T_max	0.965, 0.971
No. of measured, independent and observed [I > 2σ(I)] reflections	10209, 2603, 2210
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.612

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.116, 1.07
No. of reflections	2603
No. of parameters	215
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.49, −0.40
Computer programs: APEX2 and SAINT (Bruker, 2008), SHELXS2014 (Sheldrick, 2008 ), SHELXL2014 (Sheldrick, 2015 ), ORTEP-3 for Windows (Farrugia, 2012 ), PLATON (Spek, 2009 ) and publCIF (Westrip, 2010 ).

Structural data

CCDC reference: 1063585

Crystal structure: contains datablocks I, Global. DOI: 10.1107/S2414314616012359/su4066sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2414314616012359/su4066Isup2.hkl

Supporting information file. DOI: 10.1107/S2414314616012359/su4066Isup3.cml

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS2014 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

5-(2-Hydroxy-5-methoxybenzoyl)-1-methyl-3-nitropyridin-2(1H)-one top

Crystal data top

C₁₄H₁₂N₂O₆	F(000) = 632
M_r = 304.26	D_x = 1.487 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 12.5891 (4) Å	Cell parameters from 2062 reflections
b = 7.7739 (2) Å	θ = 2.0–25.0°
c = 14.1240 (4) Å	µ = 0.12 mm⁻¹
β = 100.466 (1)°	T = 293 K
V = 1359.27 (7) Å³	Block, colourless
Z = 4	0.30 × 0.25 × 0.25 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	2210 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.017
ω and φ scans	θ_max = 25.8°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −15→11
T_min = 0.965, T_max = 0.971	k = −9→9
10209 measured reflections	l = −17→14
2603 independent reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.116	w = 1/[σ²(F_o²) + (0.0549P)² + 0.5029P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
2603 reflections	Δρ_max = 0.49 e Å⁻³
215 parameters	Δρ_min = −0.40 e Å⁻³
2 restraints	Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0065 (17)

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.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.34903 (10)	0.35190 (18)	0.14070 (9)	0.0491 (4)
H1O	0.3954 (19)	0.328 (3)	0.1083 (17)	0.073 (7)*
O2	0.52579 (9)	0.72712 (18)	0.46370 (9)	0.0506 (3)
O3	0.15540 (9)	0.52987 (17)	0.17871 (8)	0.0450 (3)
O4	0.00621 (11)	0.1998 (2)	0.53725 (10)	0.0699 (5)
O5	−0.17278 (12)	0.3564 (3)	0.44625 (13)	0.0941 (6)
O6A	−0.1779 (5)	0.4205 (9)	0.2961 (4)	0.097 (2)	0.6
O6B	−0.1684 (7)	0.4936 (10)	0.3255 (5)	0.077 (2)	0.4
N1	0.15383 (10)	0.24178 (17)	0.47099 (9)	0.0345 (3)
N2	−0.12793 (12)	0.3882 (2)	0.37995 (13)	0.0554 (4)
C1	0.36915 (12)	0.5983 (2)	0.36290 (10)	0.0326 (3)
H1	0.3237	0.6360	0.4037	0.039*
C2	0.47843 (12)	0.6343 (2)	0.38467 (11)	0.0373 (4)
C3	0.54549 (12)	0.5717 (2)	0.32474 (12)	0.0442 (4)
H3	0.6192	0.5939	0.3394	0.053*
C4	0.50445 (13)	0.4774 (2)	0.24408 (12)	0.0428 (4)
H4	0.5509	0.4351	0.2054	0.051*
C5	0.39424 (12)	0.4444 (2)	0.21954 (11)	0.0350 (4)
C6	0.32676 (11)	0.50583 (19)	0.28016 (10)	0.0301 (3)
C7	0.20704 (11)	0.48412 (19)	0.25570 (10)	0.0310 (3)
C8	0.15132 (11)	0.40964 (19)	0.33026 (10)	0.0303 (3)
C9	0.03961 (12)	0.4296 (2)	0.32247 (11)	0.0355 (4)
H9	0.0005	0.4898	0.2707	0.043*
C10	−0.01181 (12)	0.3610 (2)	0.39050 (12)	0.0387 (4)
C11	0.04319 (13)	0.2634 (2)	0.47101 (12)	0.0406 (4)
C12	0.20469 (11)	0.31358 (19)	0.40519 (10)	0.0310 (3)
H12	0.2788	0.2975	0.4107	0.037*
C13	0.21453 (15)	0.1356 (3)	0.54895 (13)	0.0497 (5)
H13A	0.2888	0.1289	0.5417	0.075*
H13B	0.1841	0.0220	0.5459	0.075*
H13C	0.2102	0.1866	0.6100	0.075*
C14	0.45551 (15)	0.7941 (3)	0.52332 (12)	0.0505 (5)
H14A	0.4037	0.8696	0.4862	0.076*
H14B	0.4970	0.8567	0.5759	0.076*
H14C	0.4185	0.7010	0.5480	0.076*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0419 (7)	0.0648 (9)	0.0456 (7)	−0.0080 (6)	0.0214 (6)	−0.0176 (6)
O2	0.0350 (6)	0.0647 (8)	0.0491 (7)	−0.0081 (6)	−0.0002 (5)	−0.0084 (6)
O3	0.0360 (6)	0.0615 (8)	0.0359 (6)	−0.0013 (5)	0.0025 (5)	0.0080 (5)
O4	0.0531 (8)	0.0988 (12)	0.0680 (9)	0.0020 (8)	0.0378 (7)	0.0260 (8)
O5	0.0414 (8)	0.1529 (19)	0.0978 (13)	0.0083 (10)	0.0385 (8)	0.0166 (12)
O6A	0.0331 (16)	0.187 (7)	0.069 (3)	0.015 (3)	0.0041 (16)	−0.001 (3)
O6B	0.035 (3)	0.108 (5)	0.091 (5)	0.021 (3)	0.018 (3)	0.035 (4)
N1	0.0333 (7)	0.0381 (7)	0.0343 (7)	−0.0014 (6)	0.0124 (5)	−0.0002 (6)
N2	0.0297 (8)	0.0688 (11)	0.0716 (11)	0.0007 (8)	0.0197 (8)	−0.0014 (9)
C1	0.0295 (7)	0.0369 (8)	0.0322 (7)	0.0008 (6)	0.0078 (6)	0.0033 (6)
C2	0.0317 (8)	0.0398 (9)	0.0386 (8)	−0.0022 (7)	0.0021 (6)	0.0050 (7)
C3	0.0249 (7)	0.0540 (10)	0.0543 (10)	−0.0024 (7)	0.0088 (7)	0.0061 (8)
C4	0.0329 (8)	0.0509 (10)	0.0494 (10)	0.0011 (7)	0.0200 (7)	0.0007 (8)
C5	0.0345 (8)	0.0374 (8)	0.0357 (8)	−0.0017 (7)	0.0137 (6)	0.0033 (6)
C6	0.0282 (7)	0.0328 (8)	0.0308 (7)	−0.0005 (6)	0.0096 (6)	0.0052 (6)
C7	0.0305 (7)	0.0329 (8)	0.0297 (7)	0.0001 (6)	0.0063 (6)	−0.0019 (6)
C8	0.0261 (7)	0.0334 (8)	0.0329 (8)	−0.0012 (6)	0.0096 (6)	−0.0056 (6)
C9	0.0287 (7)	0.0388 (8)	0.0394 (8)	0.0005 (6)	0.0067 (6)	−0.0035 (7)
C10	0.0260 (8)	0.0435 (9)	0.0493 (9)	−0.0020 (7)	0.0144 (7)	−0.0082 (7)
C11	0.0354 (8)	0.0470 (10)	0.0443 (9)	−0.0048 (7)	0.0202 (7)	−0.0037 (7)
C12	0.0265 (7)	0.0354 (8)	0.0334 (7)	−0.0009 (6)	0.0121 (6)	−0.0044 (6)
C13	0.0462 (10)	0.0589 (11)	0.0445 (10)	0.0003 (9)	0.0097 (8)	0.0139 (8)
C14	0.0500 (10)	0.0590 (12)	0.0400 (9)	−0.0072 (9)	0.0015 (8)	−0.0078 (8)

Geometric parameters (Å, º) top

O1—C5	1.3602 (19)	C3—H3	0.9300
O1—H1O	0.83 (2)	C4—C5	1.392 (2)
O2—C2	1.3714 (19)	C4—H4	0.9300
O2—C14	1.426 (2)	C5—C6	1.395 (2)
O3—C7	1.2144 (18)	C6—C7	1.493 (2)
O4—C11	1.223 (2)	C7—C8	1.485 (2)
O5—N2	1.204 (2)	C8—C12	1.368 (2)
O6A—N2	1.261 (6)	C8—C9	1.399 (2)
O6B—N2	1.174 (8)	C9—C10	1.361 (2)
N1—C12	1.3421 (19)	C9—H9	0.9300
N1—C11	1.403 (2)	C10—C11	1.436 (2)
N1—C13	1.474 (2)	C12—H12	0.9300
N2—C10	1.458 (2)	C13—H13A	0.9600
C1—C2	1.383 (2)	C13—H13B	0.9600
C1—C6	1.393 (2)	C13—H13C	0.9600
C1—H1	0.9300	C14—H14A	0.9600
C2—C3	1.388 (2)	C14—H14B	0.9600
C3—C4	1.374 (2)	C14—H14C	0.9600

C5—O1—H1O	110.0 (16)	O3—C7—C6	121.85 (13)
C2—O2—C14	116.63 (12)	C8—C7—C6	117.83 (12)
C12—N1—C11	123.28 (13)	C12—C8—C9	117.83 (14)
C12—N1—C13	120.16 (13)	C12—C8—C7	122.20 (13)
C11—N1—C13	116.56 (13)	C9—C8—C7	119.90 (13)
O6B—N2—O5	116.3 (4)	C10—C9—C8	120.08 (15)
O5—N2—O6A	123.1 (3)	C10—C9—H9	120.0
O6B—N2—C10	118.4 (4)	C8—C9—H9	120.0
O5—N2—C10	119.62 (17)	C9—C10—C11	122.90 (14)
O6A—N2—C10	116.4 (3)	C9—C10—N2	117.90 (15)
C2—C1—C6	120.33 (14)	C11—C10—N2	119.20 (15)
C2—C1—H1	119.8	O4—C11—N1	117.87 (16)
C6—C1—H1	119.8	O4—C11—C10	128.61 (16)
O2—C2—C1	123.73 (15)	N1—C11—C10	113.53 (13)
O2—C2—C3	117.28 (14)	N1—C12—C8	122.26 (13)
C1—C2—C3	118.98 (15)	N1—C12—H12	118.9
C4—C3—C2	120.92 (14)	C8—C12—H12	118.9
C4—C3—H3	119.5	N1—C13—H13A	109.5
C2—C3—H3	119.5	N1—C13—H13B	109.5
C3—C4—C5	120.85 (15)	H13A—C13—H13B	109.5
C3—C4—H4	119.6	N1—C13—H13C	109.5
C5—C4—H4	119.6	H13A—C13—H13C	109.5
O1—C5—C4	123.47 (14)	H13B—C13—H13C	109.5
O1—C5—C6	118.19 (13)	O2—C14—H14A	109.5
C4—C5—C6	118.33 (14)	O2—C14—H14B	109.5
C1—C6—C5	120.55 (13)	H14A—C14—H14B	109.5
C1—C6—C7	117.98 (13)	O2—C14—H14C	109.5
C5—C6—C7	121.38 (13)	H14A—C14—H14C	109.5
O3—C7—C8	120.28 (13)	H14B—C14—H14C	109.5

C14—O2—C2—C1	−2.5 (2)	C12—C8—C9—C10	2.9 (2)
C14—O2—C2—C3	178.54 (15)	C7—C8—C9—C10	179.79 (14)
C6—C1—C2—O2	178.76 (14)	C8—C9—C10—C11	−1.4 (2)
C6—C1—C2—C3	−2.2 (2)	C8—C9—C10—N2	178.91 (15)
O2—C2—C3—C4	179.98 (15)	O6B—N2—C10—C9	−14.6 (5)
C1—C2—C3—C4	0.9 (2)	O5—N2—C10—C9	−167.08 (19)
C2—C3—C4—C5	1.0 (3)	O6A—N2—C10—C9	22.9 (4)
C3—C4—C5—O1	−179.97 (16)	O6B—N2—C10—C11	165.7 (4)
C3—C4—C5—C6	−1.5 (2)	O5—N2—C10—C11	13.2 (3)
C2—C1—C6—C5	1.7 (2)	O6A—N2—C10—C11	−156.8 (4)
C2—C1—C6—C7	−174.70 (14)	C12—N1—C11—O4	−176.21 (16)
O1—C5—C6—C1	178.72 (14)	C13—N1—C11—O4	3.1 (2)
C4—C5—C6—C1	0.2 (2)	C12—N1—C11—C10	3.6 (2)
O1—C5—C6—C7	−5.0 (2)	C13—N1—C11—C10	−177.08 (14)
C4—C5—C6—C7	176.48 (14)	C9—C10—C11—O4	178.07 (19)
C1—C6—C7—O3	123.47 (16)	N2—C10—C11—O4	−2.3 (3)
C5—C6—C7—O3	−52.9 (2)	C9—C10—C11—N1	−1.7 (2)
C1—C6—C7—C8	−54.42 (19)	N2—C10—C11—N1	177.93 (14)
C5—C6—C7—C8	129.20 (15)	C11—N1—C12—C8	−2.3 (2)
O3—C7—C8—C12	161.23 (15)	C13—N1—C12—C8	178.38 (15)
C6—C7—C8—C12	−20.9 (2)	C9—C8—C12—N1	−1.1 (2)
O3—C7—C8—C9	−15.5 (2)	C7—C8—C12—N1	−177.92 (13)
C6—C7—C8—C9	162.38 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O4ⁱ	0.83 (2)	1.87 (2)	2.6948 (17)	173 (2)
C4—H4···O4ⁱ	0.93	2.56	3.233 (2)	129
C14—H14B···O3ⁱⁱ	0.96	2.41	3.319 (2)	158

Symmetry codes: (i) x+1/2, −y+1/2, z−1/2; (ii) x+1/2, −y+3/2, z+1/2.

Acknowledgements

The authors thank the Department of Chemistry, IIT, Chennai, for the data collection.

References

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