The 1:1 complex of hydro­quinone and 3-methy-4-nitro­pyridine 1-oxide

In the crystal structure of the title complex, C₆H₆O₂·C₆H₆N₂O₃, 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.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](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

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Computing details

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.

(I)

Crystal data

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) Å^3	0.20 × 0.14 × 0.14 mm

Data collection

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

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.127	w = 1/[σ^2(Fo^2) + (0.077P)^2 + 0.1509P] where P = (Fo^2 + 2Fc^2)/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+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.034 (7)

Special details

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 (Ų)

	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 (Ų)

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

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—C9^i	1.379 (3)
C3—C4	1.388 (2)	C9—C8^i	1.379 (3)
C3—N2	1.468 (2)	C9—H9	0.930
C4—C5	1.389 (2)	C10—C12^ii	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—C10^ii	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—C9^i	122.79 (16)
C4—C3—N2	122.18 (15)	C7—C8—C9^i	119.76 (17)
C3—C4—C5	115.54 (15)	C8^i—C9—C7	120.22 (16)
C3—C4—C6	126.99 (15)	C8^i—C9—H9	119.9
C5—C4—C6	117.47 (15)	C7—C9—H9	119.9
N1—C5—C4	122.49 (15)	C12^ii—C10—C11	120.49 (15)
N1—C5—H5	118.8	C12^ii—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	C10^ii—C12—C11	120.42 (14)
H61—C6—H63	109.5	C10^ii—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—C9^i	−0.1 (3)
C3—C4—C5—N1	−0.9 (2)	C8—C7—C9—C8^i	0.1 (3)
C6—C4—C5—N1	179.66 (15)	C12^ii—C10—C11—O5	178.54 (15)
C4—C5—N1—O1	−179.30 (14)	C12^ii—C10—C11—C12	−0.2 (3)
C4—C5—N1—C1	−0.3 (2)	O5—C11—C12—C10^ii	−178.61 (15)
C2—C1—N1—O1	−179.41 (14)	C10—C11—C12—C10^ii	0.2 (3)

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