organic compounds
2-[(E)-(Morpholin-4-ylimino)methyl]-6-(morpholin-4-ylmethyl)phenol
aDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, bDepartment of Chemistry, College of Sciences, Shiraz University, 71454 Shiraz, Iran, and cDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, 55139 Samsun, Turkey
*Correspondence e-mail: akkurt@erciyes.edu.tr
The title compound, C16H23N3O3, contains two morpholine rings, each of which adopts a chair conformation. The molecular conformation is stabilized by an intramolecular O—H⋯N hydrogen bond, leading to a S(6) ring. In the crystal, molecules are linked into zigzag chains along the c-axis direction by C—H⋯O and C—H⋯π interactions.
CCDC reference: 961399
Related literature
For background to ); Nelson et al. (2004); Silva et al. (2011). For ring puckering parameters, see: Cremer & Pople (1975). For hydrogen-bond motifs, see: Bernstein et al. (1995).
and their applications, see: Dhar & Taploo (1982Experimental
Crystal data
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Data collection: X-AREA (Stoe & Cie, 2002); cell X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).
Supporting information
CCDC reference: 961399
10.1107/S160053681302566X/tk5257sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S160053681302566X/tk5257Isup2.hkl
Supporting information file. DOI: 10.1107/S160053681302566X/tk5257Isup3.cml
A mixture of 2-hydroxy-3-(morpholinomethyl)benzaldehyde (1.0 mmol) and morpholin-4-amine (1.0 mmol) was refluxed in EtOH for 4 h. After cooling the solution, the precipitate formed was filtered and recrystallized from ethanol to give yellow crystals in 82% yield. M. pt: 407–409 K. IR (KBr) cm-1: 1612 (C=N). 1H-NMR (250 MHz, CDCl3), δ (p.p.m.): 2.57, 3.15 (CH2N, t, 8H, J=5 Hz), 3.66 (CH2, s, 2H), 3.75, 3.88 (CH2O, t, 8H, J=5 Hz), 6.84 (aromatic H, t, 1H, J=7.5 Hz), 7.23 (aromatic H, d, 2H, J=7.5 Hz), 7.80 (HC=N, s, 1H), 11.71 (OH, s, 1H). 13C-NMR (62.9 MHz, CDCl3), δ (p.p.m): 51.8, 53.3 (CH2N), 57.6 (CH2), 66.2, 66.7 (CH2O), 118.8–139.1 (aromatic carbons), 156.0 (C=N).
All H atoms were located geometrically with O—H = 0.82 Å, and C—H = 0.93 and 0.97 Å, and refined using a riding model with Uiso(H) = 1.2Ueq(C) for the aromatic- and methylene-H atoms, and Uiso(H) = 1.5Ueq(O) for the hydroxyl-H atom.
Data collection: X-AREA (Stoe & Cie, 2002); cell
X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).C16H23N3O3 | F(000) = 656 |
Mr = 305.37 | Dx = 1.278 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 17755 reflections |
a = 9.0074 (6) Å | θ = 2.2–27.3° |
b = 15.7781 (14) Å | µ = 0.09 mm−1 |
c = 11.3083 (7) Å | T = 296 K |
β = 99.052 (5)° | Shapeless, yellow |
V = 1587.1 (2) Å3 | 0.51 × 0.32 × 0.09 mm |
Z = 4 |
STOE IPDS 2 diffractometer | 3289 independent reflections |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | 1955 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.089 |
Detector resolution: 6.67 pixels mm-1 | θmax = 26.5°, θmin = 2.2° |
ω–scans | h = −11→11 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −19→19 |
Tmin = 0.961, Tmax = 0.990 | l = −14→14 |
23637 measured reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.058 | H-atom parameters constrained |
wR(F2) = 0.123 | W = 1/[Σ2(FO2) + (0.0519P)2] WHERE P = (FO2 + 2FC2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
3289 reflections | Δρmax = 0.13 e Å−3 |
199 parameters | Δρmin = −0.12 e Å−3 |
C16H23N3O3 | V = 1587.1 (2) Å3 |
Mr = 305.37 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 9.0074 (6) Å | µ = 0.09 mm−1 |
b = 15.7781 (14) Å | T = 296 K |
c = 11.3083 (7) Å | 0.51 × 0.32 × 0.09 mm |
β = 99.052 (5)° |
STOE IPDS 2 diffractometer | 3289 independent reflections |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | 1955 reflections with I > 2σ(I) |
Tmin = 0.961, Tmax = 0.990 | Rint = 0.089 |
23637 measured reflections |
R[F2 > 2σ(F2)] = 0.058 | 0 restraints |
wR(F2) = 0.123 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.13 e Å−3 |
3289 reflections | Δρmin = −0.12 e Å−3 |
199 parameters |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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 | ||
O1 | 0.7886 (2) | 0.05694 (15) | 0.26574 (16) | 0.0912 (9) | |
O2 | 0.46117 (17) | 0.15800 (11) | 0.73906 (12) | 0.0586 (5) | |
O3 | 0.15802 (19) | 0.22570 (11) | 1.21636 (13) | 0.0659 (6) | |
N1 | 0.7555 (2) | 0.12192 (11) | 0.49469 (14) | 0.0497 (6) | |
N2 | 0.3995 (2) | 0.13953 (12) | 0.95782 (15) | 0.0500 (6) | |
N3 | 0.2980 (2) | 0.14585 (12) | 1.03797 (14) | 0.0514 (6) | |
C1 | 0.7095 (3) | 0.03684 (16) | 0.4572 (2) | 0.0669 (9) | |
C2 | 0.8012 (4) | 0.00352 (19) | 0.3670 (2) | 0.0838 (11) | |
C3 | 0.8362 (4) | 0.1393 (2) | 0.3018 (2) | 0.0859 (13) | |
C4 | 0.7453 (3) | 0.17607 (16) | 0.38952 (19) | 0.0614 (8) | |
C5 | 0.6625 (3) | 0.15608 (18) | 0.57868 (19) | 0.0667 (9) | |
C6 | 0.7055 (3) | 0.12328 (14) | 0.70585 (18) | 0.0523 (8) | |
C7 | 0.5991 (2) | 0.12627 (13) | 0.78287 (18) | 0.0467 (7) | |
C8 | 0.6357 (2) | 0.09994 (13) | 0.90283 (18) | 0.0452 (7) | |
C9 | 0.7809 (3) | 0.07110 (14) | 0.9425 (2) | 0.0562 (8) | |
C10 | 0.8869 (3) | 0.06887 (16) | 0.8678 (2) | 0.0629 (9) | |
C11 | 0.8489 (3) | 0.09507 (15) | 0.7501 (2) | 0.0600 (9) | |
C12 | 0.5296 (3) | 0.10624 (14) | 0.98800 (18) | 0.0501 (8) | |
C13 | 0.2093 (3) | 0.22298 (16) | 1.01350 (19) | 0.0584 (9) | |
C14 | 0.0910 (3) | 0.22850 (19) | 1.0939 (2) | 0.0691 (10) | |
C15 | 0.2348 (3) | 0.14835 (18) | 1.2391 (2) | 0.0707 (10) | |
C16 | 0.3593 (3) | 0.13650 (15) | 1.16513 (18) | 0.0566 (8) | |
H1A | 0.60400 | 0.03710 | 0.42230 | 0.0800* | |
H1B | 0.72160 | −0.00030 | 0.52650 | 0.0800* | |
H2 | 0.40790 | 0.15670 | 0.79150 | 0.0880* | |
H2A | 0.90580 | −0.00040 | 0.40360 | 0.1010* | |
H2B | 0.76680 | −0.05290 | 0.34220 | 0.1010* | |
H3A | 0.82770 | 0.17570 | 0.23190 | 0.1030* | |
H3B | 0.94120 | 0.13770 | 0.33800 | 0.1030* | |
H4A | 0.78230 | 0.23230 | 0.41320 | 0.0740* | |
H4B | 0.64110 | 0.18110 | 0.35220 | 0.0740* | |
H5A | 0.55830 | 0.14180 | 0.55030 | 0.0800* | |
H5B | 0.67080 | 0.21740 | 0.57950 | 0.0800* | |
H9 | 0.80660 | 0.05290 | 1.02130 | 0.0670* | |
H10 | 0.98380 | 0.04990 | 0.89600 | 0.0750* | |
H11 | 0.92120 | 0.09370 | 0.69980 | 0.0720* | |
H12 | 0.55720 | 0.08570 | 1.06540 | 0.0600* | |
H13A | 0.16130 | 0.22320 | 0.93050 | 0.0700* | |
H13B | 0.27480 | 0.27200 | 1.02640 | 0.0700* | |
H14A | 0.03510 | 0.28090 | 1.07820 | 0.0830* | |
H14B | 0.02110 | 0.18170 | 1.07680 | 0.0830* | |
H15A | 0.16360 | 0.10220 | 1.22240 | 0.0850* | |
H15B | 0.27740 | 0.14560 | 1.32330 | 0.0850* | |
H16A | 0.43750 | 0.17840 | 1.18800 | 0.0680* | |
H16B | 0.40340 | 0.08060 | 1.17960 | 0.0680* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.1117 (17) | 0.1190 (17) | 0.0446 (10) | 0.0059 (13) | 0.0173 (10) | −0.0190 (11) |
O2 | 0.0528 (9) | 0.0838 (11) | 0.0411 (8) | 0.0177 (8) | 0.0129 (7) | 0.0064 (8) |
O3 | 0.0724 (12) | 0.0822 (12) | 0.0457 (9) | 0.0009 (9) | 0.0178 (8) | −0.0106 (8) |
N1 | 0.0550 (11) | 0.0584 (12) | 0.0378 (9) | 0.0049 (9) | 0.0141 (8) | 0.0022 (8) |
N2 | 0.0553 (12) | 0.0586 (11) | 0.0379 (9) | −0.0038 (9) | 0.0128 (8) | −0.0032 (8) |
N3 | 0.0578 (11) | 0.0657 (12) | 0.0339 (9) | −0.0087 (10) | 0.0168 (8) | −0.0046 (8) |
C1 | 0.0723 (17) | 0.0674 (16) | 0.0628 (15) | −0.0028 (13) | 0.0164 (13) | 0.0056 (13) |
C2 | 0.101 (2) | 0.085 (2) | 0.0652 (17) | 0.0133 (17) | 0.0121 (16) | −0.0203 (16) |
C3 | 0.086 (2) | 0.122 (3) | 0.0555 (16) | −0.0115 (19) | 0.0288 (15) | 0.0107 (17) |
C4 | 0.0664 (15) | 0.0706 (16) | 0.0480 (13) | −0.0028 (13) | 0.0118 (11) | 0.0105 (12) |
C5 | 0.0764 (17) | 0.0838 (17) | 0.0434 (13) | 0.0302 (14) | 0.0202 (12) | 0.0073 (12) |
C6 | 0.0625 (15) | 0.0575 (14) | 0.0383 (11) | 0.0173 (11) | 0.0119 (10) | 0.0016 (10) |
C7 | 0.0533 (14) | 0.0458 (12) | 0.0409 (11) | 0.0097 (10) | 0.0070 (10) | −0.0036 (9) |
C8 | 0.0555 (14) | 0.0405 (11) | 0.0396 (11) | 0.0037 (10) | 0.0075 (10) | −0.0008 (9) |
C9 | 0.0722 (16) | 0.0564 (14) | 0.0390 (12) | 0.0141 (12) | 0.0053 (11) | 0.0014 (10) |
C10 | 0.0619 (16) | 0.0742 (16) | 0.0509 (14) | 0.0248 (13) | 0.0036 (12) | 0.0025 (12) |
C11 | 0.0608 (16) | 0.0727 (16) | 0.0494 (13) | 0.0222 (12) | 0.0177 (11) | 0.0032 (12) |
C12 | 0.0702 (17) | 0.0460 (12) | 0.0352 (11) | −0.0021 (11) | 0.0122 (11) | −0.0006 (9) |
C13 | 0.0563 (15) | 0.0766 (17) | 0.0433 (12) | 0.0045 (12) | 0.0110 (11) | 0.0012 (12) |
C14 | 0.0611 (16) | 0.099 (2) | 0.0503 (14) | −0.0016 (14) | 0.0181 (12) | −0.0086 (14) |
C15 | 0.094 (2) | 0.0805 (18) | 0.0419 (13) | −0.0078 (16) | 0.0245 (13) | −0.0040 (13) |
C16 | 0.0771 (16) | 0.0586 (15) | 0.0355 (11) | 0.0008 (12) | 0.0129 (11) | 0.0013 (10) |
O1—C2 | 1.412 (3) | C15—C16 | 1.512 (4) |
O1—C3 | 1.409 (4) | C1—H1A | 0.9700 |
O2—C7 | 1.359 (2) | C1—H1B | 0.9700 |
O3—C14 | 1.422 (3) | C2—H2A | 0.9700 |
O3—C15 | 1.406 (3) | C2—H2B | 0.9700 |
O2—H2 | 0.8200 | C3—H3A | 0.9700 |
N1—C1 | 1.449 (3) | C3—H3B | 0.9700 |
N1—C5 | 1.465 (3) | C4—H4A | 0.9700 |
N1—C4 | 1.456 (3) | C4—H4B | 0.9700 |
N2—N3 | 1.389 (2) | C5—H5A | 0.9700 |
N2—C12 | 1.281 (3) | C5—H5B | 0.9700 |
N3—C16 | 1.464 (3) | C9—H9 | 0.9300 |
N3—C13 | 1.458 (3) | C10—H10 | 0.9300 |
C1—C2 | 1.505 (4) | C11—H11 | 0.9300 |
C3—C4 | 1.499 (4) | C12—H12 | 0.9300 |
C5—C6 | 1.520 (3) | C13—H13A | 0.9700 |
C6—C7 | 1.394 (3) | C13—H13B | 0.9700 |
C6—C11 | 1.383 (4) | C14—H14A | 0.9700 |
C7—C8 | 1.407 (3) | C14—H14B | 0.9700 |
C8—C12 | 1.463 (3) | C15—H15A | 0.9700 |
C8—C9 | 1.391 (3) | C15—H15B | 0.9700 |
C9—C10 | 1.371 (4) | C16—H16A | 0.9700 |
C10—C11 | 1.384 (3) | C16—H16B | 0.9700 |
C13—C14 | 1.508 (4) | ||
C2—O1—C3 | 109.51 (19) | O1—C3—H3B | 109.00 |
C14—O3—C15 | 109.05 (18) | C4—C3—H3A | 109.00 |
C7—O2—H2 | 109.00 | C4—C3—H3B | 109.00 |
C1—N1—C5 | 111.37 (19) | H3A—C3—H3B | 108.00 |
C4—N1—C5 | 110.18 (18) | N1—C4—H4A | 110.00 |
C1—N1—C4 | 109.06 (17) | N1—C4—H4B | 110.00 |
N3—N2—C12 | 121.63 (17) | C3—C4—H4A | 110.00 |
N2—N3—C16 | 116.65 (18) | C3—C4—H4B | 110.00 |
C13—N3—C16 | 112.40 (17) | H4A—C4—H4B | 108.00 |
N2—N3—C13 | 109.48 (17) | N1—C5—H5A | 109.00 |
N1—C1—C2 | 111.1 (2) | N1—C5—H5B | 109.00 |
O1—C2—C1 | 111.0 (2) | C6—C5—H5A | 109.00 |
O1—C3—C4 | 112.1 (3) | C6—C5—H5B | 109.00 |
N1—C4—C3 | 110.0 (2) | H5A—C5—H5B | 108.00 |
N1—C5—C6 | 113.7 (2) | C8—C9—H9 | 119.00 |
C5—C6—C7 | 118.8 (2) | C10—C9—H9 | 119.00 |
C5—C6—C11 | 122.4 (2) | C9—C10—H10 | 120.00 |
C7—C6—C11 | 118.66 (19) | C11—C10—H10 | 120.00 |
O2—C7—C8 | 121.49 (17) | C6—C11—H11 | 119.00 |
C6—C7—C8 | 120.84 (18) | C10—C11—H11 | 119.00 |
O2—C7—C6 | 117.64 (18) | N2—C12—H12 | 119.00 |
C7—C8—C9 | 118.25 (18) | C8—C12—H12 | 119.00 |
C9—C8—C12 | 119.24 (19) | N3—C13—H13A | 110.00 |
C7—C8—C12 | 122.43 (18) | N3—C13—H13B | 110.00 |
C8—C9—C10 | 121.4 (2) | C14—C13—H13A | 109.00 |
C9—C10—C11 | 119.6 (2) | C14—C13—H13B | 110.00 |
C6—C11—C10 | 121.3 (2) | H13A—C13—H13B | 108.00 |
N2—C12—C8 | 121.17 (18) | O3—C14—H14A | 109.00 |
N3—C13—C14 | 110.6 (2) | O3—C14—H14B | 109.00 |
O3—C14—C13 | 110.7 (2) | C13—C14—H14A | 110.00 |
O3—C15—C16 | 113.1 (2) | C13—C14—H14B | 110.00 |
N3—C16—C15 | 109.4 (2) | H14A—C14—H14B | 108.00 |
N1—C1—H1A | 109.00 | O3—C15—H15A | 109.00 |
N1—C1—H1B | 109.00 | O3—C15—H15B | 109.00 |
C2—C1—H1A | 109.00 | C16—C15—H15A | 109.00 |
C2—C1—H1B | 109.00 | C16—C15—H15B | 109.00 |
H1A—C1—H1B | 108.00 | H15A—C15—H15B | 108.00 |
O1—C2—H2A | 109.00 | N3—C16—H16A | 110.00 |
O1—C2—H2B | 109.00 | N3—C16—H16B | 110.00 |
C1—C2—H2A | 109.00 | C15—C16—H16A | 110.00 |
C1—C2—H2B | 109.00 | C15—C16—H16B | 110.00 |
H2A—C2—H2B | 108.00 | H16A—C16—H16B | 108.00 |
O1—C3—H3A | 109.00 | ||
C2—O1—C3—C4 | −59.1 (3) | N1—C5—C6—C7 | −158.0 (2) |
C3—O1—C2—C1 | 58.2 (3) | C5—C6—C11—C10 | 177.2 (2) |
C14—O3—C15—C16 | 60.8 (3) | C11—C6—C7—O2 | 176.9 (2) |
C15—O3—C14—C13 | −61.0 (3) | C5—C6—C7—O2 | 0.6 (3) |
C1—N1—C4—C3 | −55.5 (3) | C7—C6—C11—C10 | 1.0 (3) |
C4—N1—C1—C2 | 55.8 (3) | C11—C6—C7—C8 | −1.0 (3) |
C5—N1—C4—C3 | −178.0 (2) | C5—C6—C7—C8 | −177.3 (2) |
C1—N1—C5—C6 | 78.8 (2) | O2—C7—C8—C9 | −177.62 (19) |
C4—N1—C5—C6 | −160.1 (2) | O2—C7—C8—C12 | −1.0 (3) |
C5—N1—C1—C2 | 177.6 (2) | C6—C7—C8—C12 | 176.8 (2) |
C12—N2—N3—C16 | 17.4 (3) | C6—C7—C8—C9 | 0.2 (3) |
C12—N2—N3—C13 | 146.5 (2) | C7—C8—C12—N2 | −2.9 (3) |
N3—N2—C12—C8 | −179.97 (19) | C12—C8—C9—C10 | −176.1 (2) |
C13—N3—C16—C15 | 50.3 (3) | C7—C8—C9—C10 | 0.6 (3) |
N2—N3—C13—C14 | 176.21 (18) | C9—C8—C12—N2 | 173.7 (2) |
C16—N3—C13—C14 | −52.5 (3) | C8—C9—C10—C11 | −0.6 (4) |
N2—N3—C16—C15 | 177.92 (19) | C9—C10—C11—C6 | −0.3 (4) |
N1—C1—C2—O1 | −58.0 (3) | N3—C13—C14—O3 | 57.5 (3) |
O1—C3—C4—N1 | 58.4 (3) | O3—C15—C16—N3 | −55.1 (3) |
N1—C5—C6—C11 | 25.8 (3) |
Cg3 is the centroid of the C6–C11 benzene ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···N2 | 0.82 | 1.91 | 2.636 (2) | 146 |
C13—H13A···O3i | 0.97 | 2.55 | 3.416 (3) | 149 |
C4—H4A···Cg3i | 0.97 | 2.87 | 3.646 (3) | 138 |
Symmetry code: (i) x, −y+1/2, z−1/2. |
Cg3 is the centroid of the C6–C11 benzene ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···N2 | 0.82 | 1.91 | 2.636 (2) | 146 |
C13—H13A···O3i | 0.97 | 2.55 | 3.416 (3) | 149 |
C4—H4A···Cg3i | 0.97 | 2.87 | 3.646 (3) | 138 |
Symmetry code: (i) x, −y+1/2, z−1/2. |
Acknowledgements
The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDS 2 diffractometer (purchased under grant F.279 of the University Research Fund).
References
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Schiff bases are formed by the condensation of a primary amine with a carbonyl compound (Dhar & Taploo, 1982). They are widely used for industrial purposes and also exhibit a broad range of biological activities (Silva et al., 2011). The morpholine moiety has been utilized extensively by the pharmaceutical industry in drug design, often because of the improvement in pharmacokinetic properties it can con­fer. The World Drug Index contains well over 100 drugs incorporating this structural feature, including its presence as a side-chain, scaffold, and within fused-ring systems. The biological utility of molecules containing the morpholine moiety is wide-ranging (Nelson et al., 2004). Therefore, Schiff base (I), which has the two morpholine rings, was synthesized and its X-ray structure is reported here.
The two morpholine rings (N1/O1/C1–C4 and N3/O3/C13–C16) of (I), Fig. 1, adopt a chair conformation with puckering parameters (Cremer & Pople, 1975) of QT = 0.564 (3) Å, θ = 180.0 (2)°, ϕ = 163 (33)° and QT = 0.553 (2) Å, θ = 4.6 (2)°, ϕ = 19 (3)°, respectively. The N1–C5–C6–C7, C5–C6–C7–O2, O2–C7–C8–C12 and C8–C12–N2–N3 torsion angles are -158.0 (2), 0.6 (3), -1.0 (3) and 179.97 (19)°, respectively.
An intramolecular O—H···N hydrogen bond (Table 1) stabilizes the molecular conformation of (I), forming a pseudo six-membered ring with a graph set motif S(6) (Bernstein et al., 1995). In the crystal structure, C—H···O hydrogen bonds link the molecules into infinite one-dimensional chains along [001], with a C(4) graph-set motif (Table 1, Fig. 2). Additional C—H···π interactions also assist in the stabilization of the chain.