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

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]

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• Disorder in main residue
• R factor = 0.041
• wR factor = 0.116
• Data-to-parameter ratio = 12.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of         N2 Check

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          3 Note
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          1 Report
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT300_ALERT_4_G Atom Site Occupancy of >O6A    is Constrained at        0.6 Check
PLAT300_ALERT_4_G Atom Site Occupancy of <O6B    is Constrained at        0.4 Check
PLAT301_ALERT_3_G Main Residue  Disorder ............ Percentage =          5 Note
PLAT380_ALERT_4_G Incorrectly? Oriented X(sp2)-Methyl Moiety .....        C13 Check
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          2 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         12 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density           7 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  12 ALERT level G = General information/check it is not something unexpected

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   5 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

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

Crystal data

C14H12N2O6	F(000) = 632
Mr = 304.26	Dx = 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) Å^3	Block, colourless
Z = 4	0.30 × 0.25 × 0.25 mm

Data collection

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

Refinement

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

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O4^i	0.83 (2)	1.87 (2)	2.6948 (17)	173 (2)
C4—H4···O4^i	0.93	2.56	3.233 (2)	129
C14—H14B···O3^ii	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.