organic compounds
3-Methyl-4-nitrophenol–4-dimethylaminopyridine (1/1)
aDepartment of Physics, Anna University, Chennai 600 025, India, and bCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India
*Correspondence e-mail: shirai2011@gmail.com
In the title adduct, C7H7NO3.C7H10N2, the dihedral angle betwen the benzene ring and pyridine rings is 9.60 (8)° while the nitro group attached to the benzene ring makes a dihedral angle of 21.76 (13)°. The hydroxyl O atom deviates by 0.0247 (15) Å from the plane of the benzene ring. The crystal packing features O—H⋯N hydrogen bonds.
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2008); cell SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009).
Supporting information
10.1107/S1600536812041670/pv2590sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812041670/pv2590Isup2.hkl
4-Dimethylaminopyridine and 3-methyl-4-nitrophenol were taken in equimolar (1:1) ratio using acetone as solvent. The solution was filtered in a clean beaker and optimally closed. The prepared solution was kept at room temperature for two days after which crystals suitable for X-ray diffraction were obtained.
The hydrogen atoms were placed in calculated positions with C—H = 0.93 Å to 1.08 Å refined in the riding model with fixed isotropic displacement parameters:Uiso(H) = 1.5Ueq(C) for methyl group and Uiso(H) = 1.2Ueq(C) for other groups.
Data collection: APEX2 (Bruker, 2008); cell
SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009).C7H7NO3·C7H10N2 | F(000) = 584 |
Mr = 275.31 | Dx = 1.304 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3498 reflections |
a = 11.4923 (9) Å | θ = 1.8–28.4° |
b = 9.8362 (8) Å | µ = 0.09 mm−1 |
c = 12.7781 (10) Å | T = 293 K |
β = 103.870 (5)° | Block, colourless |
V = 1402.3 (2) Å3 | 0.35 × 0.30 × 0.30 mm |
Z = 4 |
Bruker SMART APEXII area-detector diffractometer | 3498 independent reflections |
Radiation source: fine-focus sealed tube | 2469 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.028 |
ω and ϕ scans | θmax = 28.4°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | h = −15→12 |
Tmin = 0.968, Tmax = 0.973 | k = −12→13 |
13307 measured reflections | l = −16→17 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.056 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.185 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0939P)2 + 0.361P] where P = (Fo2 + 2Fc2)/3 |
3498 reflections | (Δ/σ)max = 0.001 |
184 parameters | Δρmax = 0.35 e Å−3 |
0 restraints | Δρmin = −0.27 e Å−3 |
C7H7NO3·C7H10N2 | V = 1402.3 (2) Å3 |
Mr = 275.31 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 11.4923 (9) Å | µ = 0.09 mm−1 |
b = 9.8362 (8) Å | T = 293 K |
c = 12.7781 (10) Å | 0.35 × 0.30 × 0.30 mm |
β = 103.870 (5)° |
Bruker SMART APEXII area-detector diffractometer | 3498 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | 2469 reflections with I > 2σ(I) |
Tmin = 0.968, Tmax = 0.973 | Rint = 0.028 |
13307 measured reflections |
R[F2 > 2σ(F2)] = 0.056 | 0 restraints |
wR(F2) = 0.185 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.35 e Å−3 |
3498 reflections | Δρmin = −0.27 e Å−3 |
184 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O3 | 0.15952 (12) | −0.10464 (16) | 0.99019 (11) | 0.0722 (4) | |
H3 | 0.1231 | −0.0878 | 0.9281 | 0.108* | |
N3 | −0.03318 (13) | 0.41197 (16) | 0.70694 (12) | 0.0580 (4) | |
N1 | 0.55651 (14) | 0.22673 (19) | 1.12638 (14) | 0.0661 (4) | |
O1 | 0.63106 (15) | 0.1883 (2) | 1.20437 (15) | 0.0964 (6) | |
N2 | 0.17044 (15) | 0.41211 (18) | 1.02568 (13) | 0.0637 (4) | |
C14 | 0.10524 (14) | 0.41079 (16) | 0.92229 (13) | 0.0474 (4) | |
C6 | 0.38178 (14) | 0.15782 (17) | 0.97841 (13) | 0.0475 (4) | |
C1 | 0.45173 (14) | 0.14230 (17) | 1.08398 (13) | 0.0498 (4) | |
C13 | 0.13746 (15) | 0.48787 (18) | 0.84064 (15) | 0.0524 (4) | |
H13 | 0.2061 | 0.5415 | 0.8567 | 0.063* | |
C3 | 0.32858 (16) | −0.0365 (2) | 1.12182 (14) | 0.0568 (4) | |
H3A | 0.3113 | −0.1011 | 1.1691 | 0.068* | |
C10 | 0.00038 (16) | 0.33308 (18) | 0.88898 (16) | 0.0569 (4) | |
H10 | −0.0253 | 0.2778 | 0.9381 | 0.068* | |
C5 | 0.28341 (14) | 0.07288 (18) | 0.94833 (13) | 0.0499 (4) | |
H5 | 0.2347 | 0.0806 | 0.8791 | 0.060* | |
C4 | 0.25448 (14) | −0.02386 (17) | 1.01789 (13) | 0.0507 (4) | |
C11 | −0.06391 (16) | 0.33887 (19) | 0.78414 (17) | 0.0615 (5) | |
H11 | −0.1342 | 0.2882 | 0.7652 | 0.074* | |
C2 | 0.42568 (15) | 0.0457 (2) | 1.15360 (13) | 0.0558 (4) | |
H2 | 0.4749 | 0.0369 | 1.2226 | 0.067* | |
O2 | 0.56459 (19) | 0.3367 (2) | 1.08688 (19) | 0.1206 (8) | |
C12 | 0.06747 (16) | 0.48361 (18) | 0.73744 (15) | 0.0560 (4) | |
H12 | 0.0920 | 0.5343 | 0.6852 | 0.067* | |
C7 | 0.40796 (19) | 0.2548 (2) | 0.89618 (16) | 0.0650 (5) | |
H7A | 0.3587 | 0.2327 | 0.8264 | 0.098* | |
H7B | 0.4909 | 0.2478 | 0.8948 | 0.098* | |
H7C | 0.3910 | 0.3460 | 0.9148 | 0.098* | |
C9 | 0.1410 (3) | 0.3213 (3) | 1.10553 (18) | 0.0842 (7) | |
H9A | 0.0657 | 0.3478 | 1.1194 | 0.126* | |
H9B | 0.2026 | 0.3264 | 1.1711 | 0.126* | |
H9C | 0.1353 | 0.2297 | 1.0787 | 0.126* | |
C8 | 0.26892 (19) | 0.5044 (3) | 1.06203 (19) | 0.0842 (7) | |
H8A | 0.3380 | 0.4714 | 1.0400 | 0.126* | |
H8B | 0.2870 | 0.5109 | 1.1392 | 0.126* | |
H8C | 0.2475 | 0.5926 | 1.0311 | 0.126* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O3 | 0.0643 (8) | 0.0827 (10) | 0.0624 (8) | −0.0234 (7) | 0.0014 (6) | 0.0170 (7) |
N3 | 0.0535 (8) | 0.0548 (8) | 0.0598 (9) | 0.0094 (7) | 0.0020 (6) | −0.0021 (7) |
N1 | 0.0526 (9) | 0.0713 (11) | 0.0682 (10) | −0.0036 (8) | 0.0023 (7) | −0.0149 (8) |
O1 | 0.0690 (10) | 0.1098 (13) | 0.0881 (11) | −0.0055 (9) | −0.0249 (8) | −0.0143 (10) |
N2 | 0.0660 (10) | 0.0714 (10) | 0.0511 (8) | 0.0051 (8) | 0.0087 (7) | −0.0005 (7) |
C14 | 0.0456 (8) | 0.0435 (8) | 0.0533 (9) | 0.0073 (6) | 0.0119 (6) | −0.0005 (7) |
C6 | 0.0458 (8) | 0.0496 (9) | 0.0482 (8) | 0.0043 (6) | 0.0132 (6) | −0.0018 (6) |
C1 | 0.0406 (8) | 0.0544 (9) | 0.0515 (9) | 0.0044 (7) | 0.0056 (6) | −0.0099 (7) |
C13 | 0.0444 (8) | 0.0520 (9) | 0.0602 (10) | −0.0030 (7) | 0.0112 (7) | 0.0025 (7) |
C3 | 0.0553 (9) | 0.0649 (11) | 0.0485 (9) | 0.0058 (8) | 0.0093 (7) | 0.0111 (8) |
C10 | 0.0567 (10) | 0.0480 (9) | 0.0698 (11) | −0.0029 (7) | 0.0224 (8) | 0.0054 (8) |
C5 | 0.0484 (8) | 0.0584 (9) | 0.0399 (8) | −0.0007 (7) | 0.0047 (6) | 0.0034 (7) |
C4 | 0.0459 (8) | 0.0555 (9) | 0.0488 (9) | −0.0016 (7) | 0.0078 (6) | 0.0023 (7) |
C11 | 0.0453 (9) | 0.0537 (10) | 0.0813 (13) | −0.0029 (7) | 0.0069 (8) | −0.0095 (9) |
C2 | 0.0508 (9) | 0.0687 (11) | 0.0422 (8) | 0.0103 (8) | 0.0001 (7) | −0.0002 (7) |
O2 | 0.1045 (15) | 0.1048 (15) | 0.1303 (17) | −0.0483 (12) | −0.0155 (12) | 0.0154 (13) |
C12 | 0.0585 (10) | 0.0538 (9) | 0.0563 (10) | 0.0064 (8) | 0.0150 (8) | 0.0068 (7) |
C7 | 0.0666 (11) | 0.0673 (12) | 0.0613 (11) | −0.0061 (9) | 0.0157 (9) | 0.0084 (9) |
C9 | 0.1090 (18) | 0.0927 (16) | 0.0549 (11) | 0.0277 (14) | 0.0273 (11) | 0.0153 (11) |
C8 | 0.0637 (12) | 0.115 (2) | 0.0667 (13) | 0.0000 (12) | 0.0009 (10) | −0.0245 (13) |
O3—C4 | 1.328 (2) | C3—C4 | 1.401 (2) |
O3—H3 | 0.8200 | C3—H3A | 0.9300 |
N3—C12 | 1.331 (2) | C10—C11 | 1.367 (3) |
N3—C11 | 1.335 (3) | C10—H10 | 0.9300 |
N1—O2 | 1.207 (3) | C5—C4 | 1.396 (2) |
N1—O1 | 1.209 (2) | C5—H5 | 0.9300 |
N1—C1 | 1.456 (2) | C11—H11 | 0.9300 |
N2—C14 | 1.354 (2) | C2—H2 | 0.9300 |
N2—C8 | 1.439 (3) | C12—H12 | 0.9300 |
N2—C9 | 1.456 (3) | C7—H7A | 0.9600 |
C14—C10 | 1.404 (2) | C7—H7B | 0.9600 |
C14—C13 | 1.409 (2) | C7—H7C | 0.9600 |
C6—C5 | 1.384 (2) | C9—H9A | 0.9600 |
C6—C1 | 1.403 (2) | C9—H9B | 0.9600 |
C6—C7 | 1.502 (3) | C9—H9C | 0.9600 |
C1—C2 | 1.383 (3) | C8—H8A | 0.9600 |
C13—C12 | 1.371 (3) | C8—H8B | 0.9600 |
C13—H13 | 0.9300 | C8—H8C | 0.9600 |
C3—C2 | 1.359 (2) | ||
C4—O3—H3 | 109.5 | O3—C4—C3 | 118.28 (15) |
C12—N3—C11 | 115.74 (15) | C5—C4—C3 | 118.74 (15) |
O2—N1—O1 | 121.00 (19) | N3—C11—C10 | 124.75 (16) |
O2—N1—C1 | 119.70 (17) | N3—C11—H11 | 117.6 |
O1—N1—C1 | 119.19 (19) | C10—C11—H11 | 117.6 |
C14—N2—C8 | 121.99 (18) | C3—C2—C1 | 120.37 (15) |
C14—N2—C9 | 120.72 (18) | C3—C2—H2 | 119.8 |
C8—N2—C9 | 117.27 (18) | C1—C2—H2 | 119.8 |
N2—C14—C10 | 122.35 (17) | N3—C12—C13 | 124.50 (17) |
N2—C14—C13 | 122.36 (16) | N3—C12—H12 | 117.8 |
C10—C14—C13 | 115.29 (15) | C13—C12—H12 | 117.8 |
C5—C6—C1 | 116.28 (15) | C6—C7—H7A | 109.5 |
C5—C6—C7 | 118.45 (15) | C6—C7—H7B | 109.5 |
C1—C6—C7 | 125.23 (16) | H7A—C7—H7B | 109.5 |
C2—C1—C6 | 122.06 (15) | C6—C7—H7C | 109.5 |
C2—C1—N1 | 116.10 (15) | H7A—C7—H7C | 109.5 |
C6—C1—N1 | 121.85 (17) | H7B—C7—H7C | 109.5 |
C12—C13—C14 | 119.88 (16) | N2—C9—H9A | 109.5 |
C12—C13—H13 | 120.1 | N2—C9—H9B | 109.5 |
C14—C13—H13 | 120.1 | H9A—C9—H9B | 109.5 |
C2—C3—C4 | 119.98 (16) | N2—C9—H9C | 109.5 |
C2—C3—H3A | 120.0 | H9A—C9—H9C | 109.5 |
C4—C3—H3A | 120.0 | H9B—C9—H9C | 109.5 |
C11—C10—C14 | 119.82 (17) | N2—C8—H8A | 109.5 |
C11—C10—H10 | 120.1 | N2—C8—H8B | 109.5 |
C14—C10—H10 | 120.1 | H8A—C8—H8B | 109.5 |
C6—C5—C4 | 122.56 (14) | N2—C8—H8C | 109.5 |
C6—C5—H5 | 118.7 | H8A—C8—H8C | 109.5 |
C4—C5—H5 | 118.7 | H8B—C8—H8C | 109.5 |
O3—C4—C5 | 122.98 (15) | ||
C8—N2—C14—C10 | −172.07 (18) | C13—C14—C10—C11 | −1.7 (2) |
C9—N2—C14—C10 | 6.4 (3) | C1—C6—C5—C4 | −0.3 (2) |
C8—N2—C14—C13 | 7.6 (3) | C7—C6—C5—C4 | 177.63 (17) |
C9—N2—C14—C13 | −174.00 (17) | C6—C5—C4—O3 | 179.17 (16) |
C5—C6—C1—C2 | 1.3 (2) | C6—C5—C4—C3 | −0.7 (3) |
C7—C6—C1—C2 | −176.47 (17) | C2—C3—C4—O3 | −179.11 (17) |
C5—C6—C1—N1 | −178.98 (15) | C2—C3—C4—C5 | 0.7 (3) |
C7—C6—C1—N1 | 3.2 (3) | C12—N3—C11—C10 | −0.4 (3) |
O2—N1—C1—C2 | −156.9 (2) | C14—C10—C11—N3 | 1.8 (3) |
O1—N1—C1—C2 | 19.3 (3) | C4—C3—C2—C1 | 0.2 (3) |
O2—N1—C1—C6 | 23.4 (3) | C6—C1—C2—C3 | −1.3 (3) |
O1—N1—C1—C6 | −160.43 (18) | N1—C1—C2—C3 | 178.99 (16) |
N2—C14—C13—C12 | −179.41 (16) | C11—N3—C12—C13 | −1.2 (3) |
C10—C14—C13—C12 | 0.3 (2) | C14—C13—C12—N3 | 1.2 (3) |
N2—C14—C10—C11 | 178.01 (17) |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···N3i | 0.82 | 1.79 | 2.594 (2) | 168 |
Symmetry code: (i) −x, y−1/2, −z+3/2. |
Experimental details
Crystal data | |
Chemical formula | C7H7NO3·C7H10N2 |
Mr | 275.31 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 11.4923 (9), 9.8362 (8), 12.7781 (10) |
β (°) | 103.870 (5) |
V (Å3) | 1402.3 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.35 × 0.30 × 0.30 |
Data collection | |
Diffractometer | Bruker SMART APEXII area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2008) |
Tmin, Tmax | 0.968, 0.973 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13307, 3498, 2469 |
Rint | 0.028 |
(sin θ/λ)max (Å−1) | 0.669 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.056, 0.185, 1.03 |
No. of reflections | 3498 |
No. of parameters | 184 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.35, −0.27 |
Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 and PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···N3i | 0.82 | 1.79 | 2.594 (2) | 168 |
Symmetry code: (i) −x, y−1/2, −z+3/2. |
Acknowledgements
The authors thank the TBI X-ray facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection. TS thanks the DST for an Inspire fellowship.
References
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, U. S. A. Google Scholar
Dong, S.-L. & Cheng, X. (2012). Acta Cryst. E68, o518. Web of Science CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
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In the molecule (fig.1),the pyridine ring (N3/C10/C11/C12/C13/C14) makes a dihedral angle of 9.60 (8)° with the phenyl ring (C1/C2/C3/C4/C5/C6) system. The oxygen atom O3 deviates by -0.0247 (15)Å from the plane of the phenyl ring. The carbon atom C7 deviates by deviates by 0.0677 (21)Å from the plane of the phenyl ring.
The nitrogen atom N1 deviates by -0.0285 (18)Å from the plane of the phenyl ring. The nitrogen atom N2 devaites by -0.0292 (18)Å from the plane of the pyridine ring. The crystal packing is stabilized by intermolecular O—H···N hydrogen bonds