Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807022040/fj2019sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807022040/fj2019Isup2.hkl |
CCDC reference: 651428
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (C-C) = 0.002 Å
- R factor = 0.033
- wR factor = 0.089
- Data-to-parameter ratio = 12.3
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 2.00 Ratio
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related literature, see: Moreno-Fuquen, Montaño & Atencio (2005); Wallwork & Powell (1980).
The synthesis of the title compound (I) was carried out by slow evaporation of equimolecular quantities of HQ (0.703 g, 0.0064 mol) and MQNO (1.118 g) in 100 ml of dry acetonitrile. After two days, colourless plates of a good quality, suitable for X-ray analysis, were obtained. The initial reagents were purchased from Aldrich Chemical Co., and were used without additional purification.
All non-hydrogen atoms were identified by direct methods and the positions of all the hydrogen atoms were obtained from the use of difference Fourier maps. In the final refinement, ring hydrogen atoms were constrained to geometrically sensible positions with a riding model, C—H = 0.93 Å, and Uiso(H)= 1.2Ueq(C). The H-atoms of the methyl group were assigned C—H distances of 0.96 Å, with Uiso(H)= 1.5Ueq(C). The H-atom H3H was allowed to refine freely.
The title cocrystal, C10H9NO2. 1/2(C6H6O2), belongs to a series of molecular systems based on quinoline N-oxide with diverse hydrogen-bond donors (Moreno-Fuquen et al., 2005). The synthesis and characterization of the title 6-methoxyquinoline N-oxide (MQNO) and hydroquinone (HQ) complex (I) has a threefold purpose: (a) to analyze the type of hydrogen-bonding interactions in (I), (b) to explore possible non-linear optical properties and (c) to increase the information about the MQNO system, since the structural data alone do not contain enough information.
The isoquinoline N-oxide/2-nitrobenzoic acid complex, reported by our research group (Moreno-Fuquen et al., 2005) and the free hydroquinone molecule (HQ) in the more stable form at room temperature (Wallwork & Powell, 1980) were used as reference systems to compare with the structural characteristics of the title complex. An ORTEP plot of the hydrogen bonded complex with the atomic numbering scheme is shown in Figure 1. The MQNO and HQ molecules are held together by an intermolecular hydrogen bond between the O1 atom of the N-oxide group of MQNO and the O3 atom of HQ molecule, with an O···O distance of 2.6118 (18) Å. The dihedral angle between the mean planes defined by the quinoline and hydroquinone ring atoms is 83.5 (1)°. The plane formed by methoxy group, C10—O2—C8, shows a slight deviation with respect to the mean plane of the quinoline ring atoms, showing a dihedral angle of 3.1 (1)°. The crystal packing of the title complex is stabilized by weak C1—H1···O3, [O3 with symmetry: -x + 2, -y + 2, -z + 2] intermolecular hydrogen bond. Values of these interactions can be observed in Table 2. Molecules of HQ are intertwined with two other MQNO molecules by O···O interactions. These MQNO molecules are linked to other HQ molecules, disposed about an inversion centre (-x + 2, y + 2, z - 2), by C—H···O interactions. All form chains along the [010] direction. The bond lengths and angles in both molecules are within the expected values. The presence of a centre of symmetry in the crystal precludes any nonlinear properties.
For related literature, see: Moreno-Fuquen, Montaño & Atencio (2005); Wallwork & Powell (1980).
Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS93 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: PARST95 (Nardelli, 1995).
2C10H9NO2·C6H6O2 | Z = 1 |
Mr = 460.48 | F(000) = 242 |
Triclinic, P1 | Dx = 1.394 Mg m−3 |
Hall symbol: -P 1 | Melting point: 431(1) K |
a = 7.8841 (19) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.480 (2) Å | Cell parameters from 2421 reflections |
c = 9.887 (3) Å | θ = 2.7–28.5° |
α = 95.72 (2)° | µ = 0.10 mm−1 |
β = 109.85 (3)° | T = 150 K |
γ = 113.50 (2)° | Plate, colourless |
V = 548.6 (3) Å3 | 0.18 × 0.14 × 0.04 mm |
Oxford Diffraction Gemini diffractometer | 1950 independent reflections |
Radiation source: fine-focus sealed tube | 1425 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.022 |
ω and π scans | θmax = 25.0°, θmin = 2.7° |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006) | h = −9→9 |
Tmin = 0.963, Tmax = 1.000 | k = −10→9 |
4934 measured reflections | l = −11→11 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: structure-invariant direct methods |
R[F2 > 2σ(F2)] = 0.033 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.089 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0437P)2 + 0.0161P] where P = (Fo2 + 2Fc2)/3 |
1950 reflections | (Δ/σ)max < 0.001 |
159 parameters | Δρmax = 0.13 e Å−3 |
0 restraints | Δρmin = −0.17 e Å−3 |
2C10H9NO2·C6H6O2 | γ = 113.50 (2)° |
Mr = 460.48 | V = 548.6 (3) Å3 |
Triclinic, P1 | Z = 1 |
a = 7.8841 (19) Å | Mo Kα radiation |
b = 8.480 (2) Å | µ = 0.10 mm−1 |
c = 9.887 (3) Å | T = 150 K |
α = 95.72 (2)° | 0.18 × 0.14 × 0.04 mm |
β = 109.85 (3)° |
Oxford Diffraction Gemini diffractometer | 1950 independent reflections |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006) | 1425 reflections with I > 2σ(I) |
Tmin = 0.963, Tmax = 1.000 | Rint = 0.022 |
4934 measured reflections |
R[F2 > 2σ(F2)] = 0.033 | 0 restraints |
wR(F2) = 0.089 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | Δρmax = 0.13 e Å−3 |
1950 reflections | Δρmin = −0.17 e Å−3 |
159 parameters |
Geometry. All su's (except the su in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell su's are taken into account individually in the estimation of su's in distances, angles and torsion angles; correlations between su's in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell su's is used for estimating su's involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.57431 (15) | 0.73269 (13) | 0.89892 (11) | 0.0391 (3) | |
O2 | −0.15919 (15) | 0.09469 (12) | 0.36825 (11) | 0.0373 (3) | |
O3 | 0.95539 (17) | 0.80704 (13) | 1.03706 (12) | 0.0420 (3) | |
N1 | 0.52157 (17) | 0.71447 (15) | 0.75311 (13) | 0.0290 (3) | |
C1 | 0.6280 (2) | 0.84352 (18) | 0.70459 (17) | 0.0340 (4) | |
H1 | 0.7459 | 0.9466 | 0.7747 | 0.041* | |
C2 | 0.5681 (2) | 0.82872 (19) | 0.55213 (18) | 0.0358 (4) | |
H2 | 0.6460 | 0.9213 | 0.5191 | 0.043* | |
C3 | 0.3984 (2) | 0.68218 (19) | 0.44994 (17) | 0.0334 (4) | |
H3 | 0.3562 | 0.6741 | 0.3463 | 0.040* | |
C4 | 0.2859 (2) | 0.54249 (17) | 0.49912 (15) | 0.0259 (3) | |
C5 | 0.3516 (2) | 0.55940 (17) | 0.65351 (15) | 0.0264 (3) | |
C6 | 0.2472 (2) | 0.42169 (18) | 0.70749 (16) | 0.0309 (4) | |
H6 | 0.2926 | 0.4336 | 0.8118 | 0.037* | |
C7 | 0.0807 (2) | 0.27146 (18) | 0.60868 (16) | 0.0317 (4) | |
H7 | 0.0105 | 0.1778 | 0.6446 | 0.038* | |
C8 | 0.0105 (2) | 0.25262 (17) | 0.45318 (16) | 0.0287 (3) | |
C9 | 0.1095 (2) | 0.38516 (17) | 0.39870 (16) | 0.0282 (3) | |
H9 | 0.0605 | 0.3721 | 0.2941 | 0.034* | |
C10 | −0.2312 (2) | 0.0611 (2) | 0.20879 (17) | 0.0397 (4) | |
H10A | −0.2812 | 0.1459 | 0.1767 | 0.060* | |
H10B | −0.3419 | −0.0611 | 0.1609 | 0.060* | |
H10C | −0.1197 | 0.0755 | 0.1800 | 0.060* | |
C11 | 0.8351 (2) | 0.33265 (18) | 0.94786 (15) | 0.0312 (4) | |
H11 | 0.7208 | 0.2176 | 0.9120 | 0.037* | |
C12 | 0.8066 (2) | 0.48315 (17) | 0.96332 (15) | 0.0296 (4) | |
H12 | 0.6735 | 0.4707 | 0.9378 | 0.036* | |
C13 | 0.9725 (2) | 0.65287 (17) | 1.01619 (15) | 0.0296 (4) | |
H3H | 0.816 (3) | 0.775 (2) | 0.988 (2) | 0.062 (5)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0352 (6) | 0.0466 (6) | 0.0248 (6) | 0.0164 (5) | 0.0068 (5) | −0.0011 (5) |
O2 | 0.0316 (6) | 0.0305 (5) | 0.0313 (6) | 0.0033 (5) | 0.0080 (5) | 0.0004 (4) |
O3 | 0.0328 (7) | 0.0298 (6) | 0.0471 (7) | 0.0129 (5) | 0.0036 (5) | −0.0013 (5) |
N1 | 0.0259 (7) | 0.0309 (6) | 0.0253 (7) | 0.0135 (6) | 0.0069 (5) | 0.0003 (5) |
C1 | 0.0259 (8) | 0.0247 (7) | 0.0433 (10) | 0.0085 (7) | 0.0112 (7) | 0.0025 (7) |
C2 | 0.0317 (9) | 0.0293 (8) | 0.0442 (10) | 0.0115 (7) | 0.0158 (7) | 0.0122 (7) |
C3 | 0.0337 (9) | 0.0341 (8) | 0.0334 (9) | 0.0154 (7) | 0.0144 (7) | 0.0123 (7) |
C4 | 0.0255 (8) | 0.0266 (7) | 0.0271 (8) | 0.0140 (6) | 0.0106 (6) | 0.0056 (6) |
C5 | 0.0228 (8) | 0.0276 (7) | 0.0279 (8) | 0.0132 (6) | 0.0091 (6) | 0.0023 (6) |
C6 | 0.0310 (8) | 0.0374 (8) | 0.0234 (8) | 0.0155 (7) | 0.0110 (7) | 0.0067 (7) |
C7 | 0.0309 (8) | 0.0320 (8) | 0.0317 (9) | 0.0113 (7) | 0.0158 (7) | 0.0104 (7) |
C8 | 0.0237 (8) | 0.0269 (7) | 0.0296 (9) | 0.0091 (6) | 0.0094 (6) | 0.0017 (6) |
C9 | 0.0283 (8) | 0.0307 (8) | 0.0228 (8) | 0.0140 (7) | 0.0081 (6) | 0.0039 (6) |
C10 | 0.0314 (9) | 0.0388 (8) | 0.0312 (9) | 0.0082 (7) | 0.0067 (7) | −0.0041 (7) |
C11 | 0.0273 (8) | 0.0271 (8) | 0.0263 (8) | 0.0043 (6) | 0.0076 (6) | 0.0035 (6) |
C12 | 0.0244 (8) | 0.0337 (8) | 0.0244 (8) | 0.0100 (7) | 0.0084 (6) | 0.0034 (6) |
C13 | 0.0323 (9) | 0.0285 (8) | 0.0219 (8) | 0.0122 (7) | 0.0079 (6) | 0.0026 (6) |
O1—N1 | 1.3313 (15) | C6—C7 | 1.360 (2) |
O2—C8 | 1.3684 (17) | C6—H6 | 0.9500 |
O2—C10 | 1.4363 (18) | C7—C8 | 1.414 (2) |
O3—C13 | 1.3698 (16) | C7—H7 | 0.9500 |
O3—H3H | 0.94 (2) | C8—C9 | 1.367 (2) |
N1—C1 | 1.3333 (19) | C9—H9 | 0.9500 |
N1—C5 | 1.3914 (19) | C10—H10A | 0.9800 |
C1—C2 | 1.394 (2) | C10—H10B | 0.9800 |
C1—H1 | 0.9500 | C10—H10C | 0.9800 |
C2—C3 | 1.364 (2) | C11—C12 | 1.3839 (19) |
C2—H2 | 0.9500 | C11—C13i | 1.385 (2) |
C3—C4 | 1.413 (2) | C11—H11 | 0.9500 |
C3—H3 | 0.9500 | C12—C13 | 1.393 (2) |
C4—C5 | 1.4069 (19) | C12—H12 | 0.9500 |
C4—C9 | 1.421 (2) | C13—C11i | 1.385 (2) |
C5—C6 | 1.408 (2) | ||
C8—O2—C10 | 117.18 (12) | C6—C7—C8 | 120.93 (14) |
C13—O3—H3H | 107.1 (10) | C6—C7—H7 | 119.5 |
O1—N1—C1 | 120.45 (12) | C8—C7—H7 | 119.5 |
O1—N1—C5 | 118.38 (12) | C9—C8—O2 | 125.29 (13) |
C1—N1—C5 | 121.16 (13) | C9—C8—C7 | 120.61 (13) |
N1—C1—C2 | 120.69 (13) | O2—C8—C7 | 114.10 (13) |
N1—C1—H1 | 119.7 | C8—C9—C4 | 119.74 (14) |
C2—C1—H1 | 119.7 | O2—C10—H10A | 109.5 |
C3—C2—C1 | 120.46 (15) | O2—C10—H10B | 109.5 |
C3—C2—H2 | 119.8 | H10A—C10—H10B | 109.5 |
C1—C2—H2 | 119.8 | O2—C10—H10C | 109.5 |
C2—C3—C4 | 119.66 (15) | H10A—C10—H10C | 109.5 |
C2—C3—H3 | 120.2 | H10B—C10—H10C | 109.5 |
C4—C3—H3 | 120.2 | C12—C11—C13i | 121.05 (13) |
C5—C4—C3 | 118.74 (13) | C12—C11—H11 | 119.5 |
C5—C4—C9 | 118.68 (13) | C13i—C11—H11 | 119.5 |
C3—C4—C9 | 122.58 (14) | C11—C12—C13 | 120.21 (13) |
N1—C5—C4 | 119.22 (13) | C11—C12—H12 | 119.9 |
N1—C5—C6 | 120.04 (13) | C13—C12—H12 | 119.9 |
C4—C5—C6 | 120.73 (13) | O3—C13—C11i | 118.11 (13) |
C7—C6—C5 | 119.29 (14) | O3—C13—C12 | 123.13 (13) |
C7—C6—H6 | 120.4 | C11i—C13—C12 | 118.74 (12) |
C5—C6—H6 | 120.4 | ||
O1—N1—C1—C2 | −177.08 (12) | N1—C5—C6—C7 | 179.62 (12) |
C5—N1—C1—C2 | 1.9 (2) | C4—C5—C6—C7 | −0.3 (2) |
N1—C1—C2—C3 | 0.4 (2) | C5—C6—C7—C8 | −0.5 (2) |
C1—C2—C3—C4 | −1.7 (2) | C10—O2—C8—C9 | 4.1 (2) |
C2—C3—C4—C5 | 0.6 (2) | C10—O2—C8—C7 | −175.94 (11) |
C2—C3—C4—C9 | −179.12 (13) | C6—C7—C8—C9 | 0.3 (2) |
O1—N1—C5—C4 | 176.07 (11) | C6—C7—C8—O2 | −179.64 (12) |
C1—N1—C5—C4 | −2.91 (19) | O2—C8—C9—C4 | −179.34 (12) |
O1—N1—C5—C6 | −3.88 (18) | C7—C8—C9—C4 | 0.7 (2) |
C1—N1—C5—C6 | 177.14 (12) | C5—C4—C9—C8 | −1.50 (19) |
C3—C4—C5—N1 | 1.64 (19) | C3—C4—C9—C8 | 178.22 (13) |
C9—C4—C5—N1 | −178.63 (11) | C13i—C11—C12—C13 | −0.2 (2) |
C3—C4—C5—C6 | −178.41 (12) | C11—C12—C13—O3 | −178.59 (12) |
C9—C4—C5—C6 | 1.3 (2) | C11—C12—C13—C11i | 0.2 (2) |
Symmetry code: (i) −x+2, −y+1, −z+2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3H···O1 | 0.94 (2) | 1.67 (2) | 2.6118 (18) | 176.2 (17) |
C1—H1···O3ii | 0.95 | 2.39 | 3.336 (3) | 176 |
Symmetry code: (ii) −x+2, −y+2, −z+2. |
Experimental details
Crystal data | |
Chemical formula | 2C10H9NO2·C6H6O2 |
Mr | 460.48 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 150 |
a, b, c (Å) | 7.8841 (19), 8.480 (2), 9.887 (3) |
α, β, γ (°) | 95.72 (2), 109.85 (3), 113.50 (2) |
V (Å3) | 548.6 (3) |
Z | 1 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.18 × 0.14 × 0.04 |
Data collection | |
Diffractometer | Oxford Diffraction Gemini |
Absorption correction | Multi-scan (CrysAlis RED; Oxford Diffraction, 2006) |
Tmin, Tmax | 0.963, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4934, 1950, 1425 |
Rint | 0.022 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.033, 0.089, 1.08 |
No. of reflections | 1950 |
No. of parameters | 159 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.13, −0.17 |
Computer programs: CrysAlis CCD (Oxford Diffraction, 2006), CrysAlis RED (Oxford Diffraction, 2006), CrysAlis RED, SHELXS93 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), PARST95 (Nardelli, 1995).
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3H···O1 | 0.94 (2) | 1.67 (2) | 2.6118 (18) | 176.2 (17) |
C1—H1···O3i | 0.95 | 2.39 | 3.336 (3) | 176 |
Symmetry code: (i) −x+2, −y+2, −z+2. |
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The title cocrystal, C10H9NO2. 1/2(C6H6O2), belongs to a series of molecular systems based on quinoline N-oxide with diverse hydrogen-bond donors (Moreno-Fuquen et al., 2005). The synthesis and characterization of the title 6-methoxyquinoline N-oxide (MQNO) and hydroquinone (HQ) complex (I) has a threefold purpose: (a) to analyze the type of hydrogen-bonding interactions in (I), (b) to explore possible non-linear optical properties and (c) to increase the information about the MQNO system, since the structural data alone do not contain enough information.
The isoquinoline N-oxide/2-nitrobenzoic acid complex, reported by our research group (Moreno-Fuquen et al., 2005) and the free hydroquinone molecule (HQ) in the more stable form at room temperature (Wallwork & Powell, 1980) were used as reference systems to compare with the structural characteristics of the title complex. An ORTEP plot of the hydrogen bonded complex with the atomic numbering scheme is shown in Figure 1. The MQNO and HQ molecules are held together by an intermolecular hydrogen bond between the O1 atom of the N-oxide group of MQNO and the O3 atom of HQ molecule, with an O···O distance of 2.6118 (18) Å. The dihedral angle between the mean planes defined by the quinoline and hydroquinone ring atoms is 83.5 (1)°. The plane formed by methoxy group, C10—O2—C8, shows a slight deviation with respect to the mean plane of the quinoline ring atoms, showing a dihedral angle of 3.1 (1)°. The crystal packing of the title complex is stabilized by weak C1—H1···O3, [O3 with symmetry: -x + 2, -y + 2, -z + 2] intermolecular hydrogen bond. Values of these interactions can be observed in Table 2. Molecules of HQ are intertwined with two other MQNO molecules by O···O interactions. These MQNO molecules are linked to other HQ molecules, disposed about an inversion centre (-x + 2, y + 2, z - 2), by C—H···O interactions. All form chains along the [010] direction. The bond lengths and angles in both molecules are within the expected values. The presence of a centre of symmetry in the crystal precludes any nonlinear properties.