In the crystal structure of the title complex, C
6H
6O
2·C
6H
6N
2O
3, the molecules are linked by intermolecular hydrogen bonds between the O—H and N—O groups. The O atom of the
N-oxide group of 3-methyl-4-nitropyridine 1-oxide acts as an acceptor for hydrogen bonds from O—H groups of two symmetry-related hydroquinone molecules [O
O 2.732 (2) and 2.810 (2) Å]. The angles between the rings of the 3-methyl-4-nitropyridine 1-oxide and two hydroquinone molecules are 6.1 (3) and 0.6 (3)°. The crystal structure exhibits overlap between the aromatic rings of the molecules in the [11
] direction.
Supporting information
CCDC reference: 189375
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.002 Å
- R factor = 0.043
- wR factor = 0.127
- Data-to-parameter ratio = 11.6
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Data collection: MSC/AFC Diffractometer Control Software
(Molecular Structure Corporation, 1993); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1995); program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and ZORTEP (Zsolnai, 1995); software used to prepare material for publication: SHELXL97.
Crystal data top
C6H6O2·C6H6N2O3 | Z = 2 |
Mr = 264.24 | F(000) = 276 |
Triclinic, P1 | Dx = 1.473 Mg m−3 |
Hall symbol: -P 1 | Melting point: 384(1) K |
a = 7.8593 (16) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.429 (3) Å | Cell parameters from 25 reflections |
c = 9.039 (3) Å | θ = 8–20° |
α = 84.39 (3)° | µ = 0.12 mm−1 |
β = 89.92 (2)° | T = 293 K |
γ = 88.91 (3)° | Irregular_block, orange–red |
V = 595.8 (3) Å3 | 0.20 × 0.14 × 0.14 mm |
Data collection top
Rigaku AFC-7S diffractometer | Rint = 0.015 |
Radiation source: fine-focus sealed tube | θmax = 25.0°, θmin = 2.3° |
Graphite monochromator | h = −9→9 |
ω/2θ scans | k = −10→0 |
2250 measured reflections | l = −10→10 |
2091 independent reflections | 3 standard reflections every 150 min |
1848 reflections with I > 2σ(I) | intensity decay: none |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.043 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.127 | w = 1/[σ2(Fo2) + (0.077P)2 + 0.1509P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
2091 reflections | Δρmax = 0.29 e Å−3 |
181 parameters | Δρmin = −0.22 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.034 (7) |
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 | Uiso*/Ueq | |
C1 | 0.3953 (2) | 0.55619 (19) | 0.68901 (18) | 0.0419 (4) | |
H1 | 0.4661 | 0.4711 | 0.6696 | 0.050* | |
C2 | 0.4149 (2) | 0.6282 (2) | 0.81648 (18) | 0.0421 (4) | |
H2 | 0.4973 | 0.5907 | 0.8856 | 0.051* | |
C3 | 0.3119 (2) | 0.75697 (19) | 0.84251 (17) | 0.0381 (4) | |
C4 | 0.1868 (2) | 0.81540 (18) | 0.74227 (18) | 0.0374 (4) | |
C5 | 0.1717 (2) | 0.73451 (19) | 0.61632 (18) | 0.0395 (4) | |
H5 | 0.0886 | 0.7683 | 0.5465 | 0.047* | |
C6 | 0.0674 (2) | 0.9538 (2) | 0.7568 (2) | 0.0536 (5) | |
H61 | −0.0163 | 0.9587 | 0.6792 | 0.064* | |
H62 | 0.1303 | 1.0509 | 0.7487 | 0.064* | |
H63 | 0.0119 | 0.9406 | 0.8517 | 0.064* | |
N1 | 0.27269 (17) | 0.60914 (15) | 0.59155 (14) | 0.0374 (3) | |
N2 | 0.3422 (2) | 0.82778 (19) | 0.98195 (17) | 0.0524 (4) | |
O1 | 0.25402 (17) | 0.53780 (15) | 0.46953 (13) | 0.0515 (4) | |
O2 | 0.2858 (3) | 0.9599 (2) | 0.99536 (19) | 0.0919 (6) | |
O3 | 0.4255 (3) | 0.7501 (2) | 1.07750 (17) | 0.0854 (6) | |
C7 | −0.1063 (2) | 0.6283 (2) | 0.02089 (19) | 0.0456 (4) | |
H7 | −0.1782 | 0.7146 | 0.0344 | 0.055* | |
C8 | 0.0043 (2) | 0.5704 (2) | 0.13225 (18) | 0.0428 (4) | |
C9 | −0.1105 (2) | 0.5577 (2) | −0.11172 (18) | 0.0447 (4) | |
H9 | −0.1851 | 0.5970 | −0.1868 | 0.054* | |
C10 | 0.4654 (2) | 0.11298 (18) | 0.59675 (17) | 0.0398 (4) | |
H10 | 0.4426 | 0.1891 | 0.6623 | 0.048* | |
C11 | 0.3716 (2) | 0.11380 (18) | 0.46727 (18) | 0.0386 (4) | |
C12 | 0.4074 (2) | −0.00009 (19) | 0.37064 (17) | 0.0409 (4) | |
H12 | 0.3453 | −0.0004 | 0.2832 | 0.049* | |
O4 | 0.0002 (2) | 0.64284 (19) | 0.26215 (16) | 0.0637 (4) | |
HO4 | 0.080 (4) | 0.605 (3) | 0.312 (3) | 0.087 (9)* | |
O5 | 0.24142 (17) | 0.22086 (16) | 0.43064 (16) | 0.0564 (4) | |
HO5 | 0.250 (3) | 0.306 (3) | 0.469 (3) | 0.063 (6)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0490 (9) | 0.0359 (8) | 0.0404 (9) | 0.0105 (7) | 0.0005 (7) | −0.0042 (7) |
C2 | 0.0474 (9) | 0.0399 (9) | 0.0382 (8) | 0.0047 (7) | −0.0072 (7) | −0.0009 (7) |
C3 | 0.0452 (9) | 0.0369 (8) | 0.0333 (8) | −0.0041 (7) | −0.0009 (6) | −0.0085 (6) |
C4 | 0.0413 (8) | 0.0330 (8) | 0.0387 (8) | 0.0004 (6) | 0.0010 (6) | −0.0079 (6) |
C5 | 0.0434 (9) | 0.0374 (8) | 0.0378 (8) | 0.0055 (7) | −0.0055 (7) | −0.0059 (7) |
C6 | 0.0532 (11) | 0.0480 (10) | 0.0619 (11) | 0.0125 (8) | −0.0072 (9) | −0.0196 (8) |
N1 | 0.0481 (8) | 0.0348 (7) | 0.0301 (7) | 0.0026 (6) | 0.0007 (5) | −0.0075 (5) |
N2 | 0.0635 (10) | 0.0530 (9) | 0.0430 (8) | 0.0006 (7) | −0.0097 (7) | −0.0174 (7) |
O1 | 0.0726 (9) | 0.0487 (7) | 0.0355 (6) | 0.0105 (6) | −0.0046 (6) | −0.0185 (5) |
O2 | 0.1312 (16) | 0.0763 (11) | 0.0748 (11) | 0.0353 (10) | −0.0339 (10) | −0.0477 (9) |
O3 | 0.1185 (14) | 0.0848 (11) | 0.0555 (9) | 0.0190 (10) | −0.0414 (9) | −0.0232 (8) |
C7 | 0.0523 (10) | 0.0404 (9) | 0.0436 (9) | 0.0070 (7) | −0.0031 (7) | −0.0026 (7) |
C8 | 0.0520 (10) | 0.0417 (9) | 0.0350 (8) | −0.0026 (7) | −0.0025 (7) | −0.0043 (7) |
C9 | 0.0491 (9) | 0.0465 (10) | 0.0371 (9) | 0.0039 (7) | −0.0095 (7) | 0.0017 (7) |
C10 | 0.0513 (9) | 0.0345 (8) | 0.0347 (8) | −0.0008 (7) | −0.0068 (7) | −0.0089 (6) |
C11 | 0.0451 (9) | 0.0318 (8) | 0.0389 (8) | 0.0002 (6) | −0.0091 (7) | −0.0030 (6) |
C12 | 0.0512 (9) | 0.0384 (9) | 0.0336 (8) | −0.0001 (7) | −0.0126 (7) | −0.0054 (6) |
O4 | 0.0850 (11) | 0.0638 (9) | 0.0447 (8) | 0.0164 (8) | −0.0149 (7) | −0.0203 (6) |
O5 | 0.0631 (8) | 0.0441 (7) | 0.0636 (8) | 0.0154 (6) | −0.0277 (6) | −0.0170 (6) |
Geometric parameters (Å, º) top
C1—N1 | 1.346 (2) | C7—C8 | 1.377 (3) |
C1—C2 | 1.364 (2) | C7—C9 | 1.390 (2) |
C1—H1 | 0.930 | C7—H7 | 0.930 |
C2—C3 | 1.380 (2) | C8—O4 | 1.375 (2) |
C2—H2 | 0.930 | C8—C9i | 1.379 (3) |
C3—C4 | 1.388 (2) | C9—C8i | 1.379 (3) |
C3—N2 | 1.468 (2) | C9—H9 | 0.930 |
C4—C5 | 1.389 (2) | C10—C12ii | 1.379 (2) |
C4—C6 | 1.499 (2) | C10—C11 | 1.384 (2) |
C5—N1 | 1.346 (2) | C10—H10 | 0.930 |
C5—H5 | 0.930 | C11—O5 | 1.370 (2) |
C6—H61 | 0.960 | C11—C12 | 1.385 (2) |
C6—H62 | 0.960 | C12—C10ii | 1.379 (2) |
C6—H63 | 0.960 | C12—H12 | 0.930 |
N1—O1 | 1.3165 (17) | O4—HO4 | 0.82 (3) |
N2—O2 | 1.208 (2) | O5—HO5 | 0.83 (2) |
N2—O3 | 1.216 (2) | | |
| | | |
N1—C1—C2 | 119.55 (14) | O2—N2—O3 | 123.45 (16) |
N1—C1—H1 | 120.2 | O2—N2—C3 | 118.86 (16) |
C2—C1—H1 | 120.2 | O3—N2—C3 | 117.68 (16) |
C1—C2—C3 | 119.77 (15) | C8—C7—C9 | 120.02 (17) |
C1—C2—H2 | 120.1 | C8—C7—H7 | 120.0 |
C3—C2—H2 | 120.1 | C9—C7—H7 | 120.0 |
C2—C3—C4 | 121.64 (15) | O4—C8—C7 | 117.43 (17) |
C2—C3—N2 | 116.19 (15) | O4—C8—C9i | 122.79 (16) |
C4—C3—N2 | 122.18 (15) | C7—C8—C9i | 119.76 (17) |
C3—C4—C5 | 115.54 (15) | C8i—C9—C7 | 120.22 (16) |
C3—C4—C6 | 126.99 (15) | C8i—C9—H9 | 119.9 |
C5—C4—C6 | 117.47 (15) | C7—C9—H9 | 119.9 |
N1—C5—C4 | 122.49 (15) | C12ii—C10—C11 | 120.49 (15) |
N1—C5—H5 | 118.8 | C12ii—C10—H10 | 119.8 |
C4—C5—H5 | 118.8 | C11—C10—H10 | 119.8 |
C4—C6—H61 | 109.5 | O5—C11—C10 | 123.05 (15) |
C4—C6—H62 | 109.5 | O5—C11—C12 | 117.85 (14) |
H61—C6—H62 | 109.5 | C10—C11—C12 | 119.09 (15) |
C4—C6—H63 | 109.5 | C10ii—C12—C11 | 120.42 (14) |
H61—C6—H63 | 109.5 | C10ii—C12—H12 | 119.8 |
H62—C6—H63 | 109.5 | C11—C12—H12 | 119.8 |
O1—N1—C5 | 120.00 (14) | C8—O4—HO4 | 106 (2) |
O1—N1—C1 | 119.01 (13) | C11—O5—HO5 | 113.9 (16) |
C5—N1—C1 | 120.98 (14) | | |
| | | |
N1—C1—C2—C3 | −1.6 (3) | C2—C1—N1—C5 | 1.6 (2) |
C1—C2—C3—C4 | 0.5 (3) | C2—C3—N2—O2 | 163.02 (19) |
C1—C2—C3—N2 | −179.68 (15) | C4—C3—N2—O2 | −17.1 (3) |
C2—C3—C4—C5 | 0.8 (2) | C2—C3—N2—O3 | −16.0 (3) |
N2—C3—C4—C5 | −179.09 (14) | C4—C3—N2—O3 | 163.90 (18) |
C2—C3—C4—C6 | −179.82 (16) | C9—C7—C8—O4 | −178.64 (16) |
N2—C3—C4—C6 | 0.3 (3) | C9—C7—C8—C9i | −0.1 (3) |
C3—C4—C5—N1 | −0.9 (2) | C8—C7—C9—C8i | 0.1 (3) |
C6—C4—C5—N1 | 179.66 (15) | C12ii—C10—C11—O5 | 178.54 (15) |
C4—C5—N1—O1 | −179.30 (14) | C12ii—C10—C11—C12 | −0.2 (3) |
C4—C5—N1—C1 | −0.3 (2) | O5—C11—C12—C10ii | −178.61 (15) |
C2—C1—N1—O1 | −179.41 (14) | C10—C11—C12—C10ii | 0.2 (3) |
Symmetry codes: (i) −x, −y+1, −z; (ii) −x+1, −y, −z+1. |