Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801016324/na6100sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801016324/na6100Isup2.hkl |
CCDC reference: 176021
The title compound (I) was prepared by hydrochloric-acid-catalysed ring-opening reaction of syn-1-Acetyl-5'a-hydro-spiro[3H-indole-3,2'](2a'H)oxeto[2,3-b] benzofuran-2(1H)-one in benzene solution. Single crystals suitable for an X-ray diffraction were obtained by slow evaporation from a mixture of petroleum ether–acetone solution.
After checking their presence in the difference map, all H-atoms were geometrically fixed and allowed to ride on the parent C atoms and refined isotropically. Owing to a not-so-good quality of the crystals and a large fraction of weak data at higher angles, the R[F2>2σ(F2)] value is rather high and the completeness is less than 0.96, even though the 2θ maximum was limited to 50°.
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).
Fig. 1. The structure of (I) showing 50% probability displacement ellipsoids and the atom-numbering scheme. | |
Fig. 2. Packing diagram of the structure (I) viewed down the c axis. |
C18H13NO4 | F(000) = 320 |
Mr = 307.29 | Dx = 1.417 Mg m−3 |
Triclinic, P1 | Melting point: 383K K |
a = 7.5900 (6) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.6858 (8) Å | Cell parameters from 2226 reflections |
c = 10.4040 (9) Å | θ = 2.0–29.5° |
α = 74.141 (2)° | µ = 0.10 mm−1 |
β = 83.650 (2)° | T = 293 K |
γ = 78.772 (2)° | Block, colorless |
V = 720.3 (1) Å3 | 0.36 × 0.24 × 0.18 mm |
Z = 2 |
Siemens SMART CCD area detector diffractometer | 2421 independent reflections |
Radiation source: fine-focus sealed tube | 1233 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.091 |
Detector resolution: 8.33 pixels mm-1 | θmax = 25.0°, θmin = 2.0° |
ω scans | h = −9→8 |
Absorption correction: empirical (using intensity measurements) SADABS (Sheldrick, 1996) | k = −11→10 |
Tmin = 0.965, Tmax = 0.982 | l = −12→10 |
3999 measured reflections |
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)] = 0.072 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.174 | w = 1/[σ2(Fo2) + (0.039P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.86 | (Δ/σ)max < 0.001 |
2421 reflections | Δρmax = 0.30 e Å−3 |
214 parameters | Δρmin = −0.31 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.133 (14) |
C18H13NO4 | γ = 78.772 (2)° |
Mr = 307.29 | V = 720.3 (1) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.5900 (6) Å | Mo Kα radiation |
b = 9.6858 (8) Å | µ = 0.10 mm−1 |
c = 10.4040 (9) Å | T = 293 K |
α = 74.141 (2)° | 0.36 × 0.24 × 0.18 mm |
β = 83.650 (2)° |
Siemens SMART CCD area detector diffractometer | 2421 independent reflections |
Absorption correction: empirical (using intensity measurements) SADABS (Sheldrick, 1996) | 1233 reflections with I > 2σ(I) |
Tmin = 0.965, Tmax = 0.982 | Rint = 0.091 |
3999 measured reflections |
R[F2 > 2σ(F2)] = 0.072 | 0 restraints |
wR(F2) = 0.174 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.86 | Δρmax = 0.30 e Å−3 |
2421 reflections | Δρmin = −0.31 e Å−3 |
214 parameters |
Experimental. The data collection covered over a hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different ϕ angle (0, 88 and 180°) for the crystal and each exposure of 10 s covered 0.3° in ω. The crystal-to-detector distance was 4 cm and the detector swing angle was -35°. Crystal decay was monitored by repeating fifty initial frames at the end of data collection and analysing the intensity of duplicate reflections, and was found to be negligible. |
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. |
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 > σ(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 | ||
O1 | 1.0255 (3) | 0.3011 (3) | 1.0070 (3) | 0.0569 (8) | |
O2 | 0.4559 (3) | 0.3894 (3) | 0.8736 (3) | 0.0524 (8) | |
O3 | 0.6435 (4) | 0.1983 (3) | 0.7059 (3) | 0.0546 (8) | |
O4 | 0.7760 (4) | 0.4837 (3) | 0.3466 (3) | 0.0630 (8) | |
N1 | 0.7128 (4) | 0.4195 (3) | 0.5713 (3) | 0.0392 (7) | |
C1 | 0.9184 (5) | 0.3920 (4) | 0.9110 (4) | 0.0506 (10) | |
H1A | 0.9451 | 0.4803 | 0.8575 | 0.061* | |
C2 | 0.9391 (5) | 0.1833 (4) | 1.0637 (4) | 0.0430 (9) | |
C3 | 1.0016 (5) | 0.0626 (4) | 1.1637 (4) | 0.0504 (10) | |
H3A | 1.1098 | 0.0536 | 1.2020 | 0.061* | |
C4 | 0.8961 (5) | −0.0433 (4) | 1.2039 (4) | 0.0507 (10) | |
H4A | 0.9339 | −0.1269 | 1.2705 | 0.061* | |
C5 | 0.7330 (5) | −0.0281 (4) | 1.1466 (4) | 0.0528 (10) | |
H5A | 0.6637 | −0.1013 | 1.1770 | 0.063* | |
C6 | 0.6719 (5) | 0.0930 (4) | 1.0462 (4) | 0.0468 (10) | |
H6A | 0.5636 | 0.1021 | 1.0082 | 0.056* | |
C7 | 0.7794 (5) | 0.2016 (3) | 1.0034 (3) | 0.0387 (9) | |
C8 | 0.7680 (4) | 0.3392 (3) | 0.9021 (3) | 0.0380 (9) | |
C9 | 0.6267 (5) | 0.4061 (3) | 0.8034 (3) | 0.0399 (9) | |
C10 | 0.6608 (4) | 0.3223 (4) | 0.6925 (3) | 0.0373 (9) | |
C11 | 0.6940 (4) | 0.5627 (3) | 0.5910 (3) | 0.0373 (9) | |
C12 | 0.7191 (5) | 0.6924 (4) | 0.4996 (4) | 0.0508 (10) | |
H12A | 0.7554 | 0.6959 | 0.4106 | 0.061* | |
C13 | 0.6877 (5) | 0.8172 (4) | 0.5461 (4) | 0.0535 (11) | |
H13A | 0.7026 | 0.9057 | 0.4864 | 0.064* | |
C14 | 0.6362 (5) | 0.8138 (4) | 0.6761 (4) | 0.0533 (11) | |
H14A | 0.6147 | 0.8996 | 0.7035 | 0.064* | |
C15 | 0.6154 (5) | 0.6839 (4) | 0.7678 (4) | 0.0507 (10) | |
H15A | 0.5839 | 0.6809 | 0.8574 | 0.061* | |
C16 | 0.6420 (4) | 0.5586 (3) | 0.7243 (3) | 0.0385 (9) | |
C17 | 0.7630 (5) | 0.3847 (4) | 0.4477 (4) | 0.0447 (9) | |
C18 | 0.7987 (6) | 0.2292 (4) | 0.4452 (4) | 0.0650 (12) | |
H18A | 0.8736 | 0.1732 | 0.5165 | 0.097* | |
H18B | 0.8588 | 0.2201 | 0.3609 | 0.097* | |
H18C | 0.6869 | 0.1938 | 0.4564 | 0.097* | |
H2A | 0.359 (5) | 0.447 (3) | 0.818 (4) | 0.056 (11)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0574 (17) | 0.0555 (16) | 0.067 (2) | −0.0260 (13) | −0.0204 (15) | −0.0133 (13) |
O2 | 0.0431 (15) | 0.0678 (18) | 0.0403 (17) | −0.0134 (13) | 0.0023 (13) | −0.0030 (13) |
O3 | 0.079 (2) | 0.0406 (15) | 0.0519 (18) | −0.0261 (13) | −0.0107 (15) | −0.0112 (12) |
O4 | 0.082 (2) | 0.0761 (19) | 0.0350 (17) | −0.0253 (16) | 0.0035 (15) | −0.0157 (15) |
N1 | 0.0486 (18) | 0.0426 (17) | 0.0289 (17) | −0.0168 (14) | −0.0009 (14) | −0.0080 (13) |
C1 | 0.059 (2) | 0.046 (2) | 0.052 (3) | −0.0161 (19) | −0.018 (2) | −0.0096 (18) |
C2 | 0.049 (2) | 0.046 (2) | 0.040 (2) | −0.0130 (17) | −0.0072 (18) | −0.0168 (17) |
C3 | 0.057 (2) | 0.055 (2) | 0.041 (2) | −0.003 (2) | −0.017 (2) | −0.0135 (18) |
C4 | 0.065 (3) | 0.044 (2) | 0.037 (2) | −0.0015 (19) | −0.004 (2) | −0.0043 (17) |
C5 | 0.059 (2) | 0.050 (2) | 0.046 (2) | −0.0138 (19) | 0.000 (2) | −0.0052 (18) |
C6 | 0.049 (2) | 0.047 (2) | 0.044 (2) | −0.0167 (17) | −0.0023 (19) | −0.0073 (18) |
C7 | 0.048 (2) | 0.0396 (19) | 0.031 (2) | −0.0094 (16) | −0.0061 (17) | −0.0104 (15) |
C8 | 0.045 (2) | 0.044 (2) | 0.030 (2) | −0.0149 (17) | −0.0035 (16) | −0.0123 (15) |
C9 | 0.049 (2) | 0.046 (2) | 0.026 (2) | −0.0151 (17) | 0.0042 (17) | −0.0089 (16) |
C10 | 0.0347 (19) | 0.042 (2) | 0.040 (2) | −0.0082 (16) | −0.0092 (16) | −0.0146 (16) |
C11 | 0.0384 (19) | 0.040 (2) | 0.038 (2) | −0.0170 (16) | −0.0032 (17) | −0.0099 (16) |
C12 | 0.067 (3) | 0.050 (2) | 0.038 (2) | −0.029 (2) | 0.0031 (19) | −0.0043 (18) |
C13 | 0.066 (3) | 0.041 (2) | 0.053 (3) | −0.0220 (19) | 0.000 (2) | −0.0044 (19) |
C14 | 0.055 (2) | 0.043 (2) | 0.066 (3) | −0.0087 (18) | −0.009 (2) | −0.018 (2) |
C15 | 0.061 (3) | 0.047 (2) | 0.049 (3) | −0.0110 (19) | −0.003 (2) | −0.0195 (19) |
C16 | 0.043 (2) | 0.038 (2) | 0.038 (2) | −0.0111 (16) | −0.0035 (17) | −0.0119 (16) |
C17 | 0.040 (2) | 0.064 (2) | 0.036 (2) | −0.0160 (18) | −0.0041 (18) | −0.0172 (19) |
C18 | 0.079 (3) | 0.070 (3) | 0.055 (3) | −0.015 (2) | 0.005 (2) | −0.032 (2) |
O1—C1 | 1.362 (4) | C6—H6A | 0.9300 |
O1—C2 | 1.385 (4) | C7—C8 | 1.450 (4) |
O2—C9 | 1.430 (4) | C8—C9 | 1.494 (5) |
O2—H2A | 0.97 (3) | C9—C16 | 1.502 (4) |
O3—C10 | 1.202 (4) | C9—C10 | 1.556 (5) |
O4—C17 | 1.224 (4) | C11—C12 | 1.386 (4) |
N1—C17 | 1.411 (5) | C11—C16 | 1.391 (5) |
N1—C10 | 1.420 (4) | C12—C13 | 1.391 (5) |
N1—C11 | 1.434 (4) | C12—H12A | 0.9300 |
C1—C8 | 1.360 (5) | C13—C14 | 1.359 (6) |
C1—H1A | 0.9300 | C13—H13A | 0.9300 |
C2—C3 | 1.379 (5) | C14—C15 | 1.381 (5) |
C2—C7 | 1.385 (4) | C14—H14A | 0.9300 |
C3—C4 | 1.371 (5) | C15—C16 | 1.379 (5) |
C3—H3A | 0.9300 | C15—H15A | 0.9300 |
C4—C5 | 1.398 (5) | C17—C18 | 1.484 (5) |
C4—H4A | 0.9300 | C18—H18A | 0.9600 |
C5—C6 | 1.381 (5) | C18—H18B | 0.9600 |
C5—H5A | 0.9300 | C18—H18C | 0.9600 |
C6—C7 | 1.403 (5) | ||
C1—O1—C2 | 106.0 (3) | C8—C9—C10 | 107.9 (3) |
C9—O2—H2A | 110 (2) | C16—C9—C10 | 102.0 (3) |
C17—N1—C10 | 125.8 (3) | O3—C10—N1 | 125.9 (3) |
C17—N1—C11 | 124.7 (3) | O3—C10—C9 | 126.3 (3) |
C10—N1—C11 | 109.3 (3) | N1—C10—C9 | 107.8 (3) |
C8—C1—O1 | 112.5 (3) | C12—C11—C16 | 120.7 (3) |
C8—C1—H1A | 123.8 | C12—C11—N1 | 129.6 (3) |
O1—C1—H1A | 123.8 | C16—C11—N1 | 109.7 (3) |
C3—C2—C7 | 123.9 (3) | C11—C12—C13 | 117.4 (4) |
C3—C2—O1 | 126.0 (3) | C11—C12—H12A | 121.3 |
C7—C2—O1 | 110.1 (3) | C13—C12—H12A | 121.3 |
C4—C3—C2 | 116.6 (3) | C14—C13—C12 | 122.1 (3) |
C4—C3—H3A | 121.7 | C14—C13—H13A | 119.0 |
C2—C3—H3A | 121.7 | C12—C13—H13A | 119.0 |
C3—C4—C5 | 121.3 (3) | C13—C14—C15 | 120.5 (4) |
C3—C4—H4A | 119.4 | C13—C14—H14A | 119.8 |
C5—C4—H4A | 119.4 | C15—C14—H14A | 119.8 |
C6—C5—C4 | 121.7 (4) | C16—C15—C14 | 118.9 (4) |
C6—C5—H5A | 119.2 | C16—C15—H15A | 120.6 |
C4—C5—H5A | 119.2 | C14—C15—H15A | 120.6 |
C5—C6—C7 | 117.6 (3) | C15—C16—C11 | 120.5 (3) |
C5—C6—H6A | 121.2 | C15—C16—C9 | 128.9 (3) |
C7—C6—H6A | 121.2 | C11—C16—C9 | 110.6 (3) |
C2—C7—C6 | 119.0 (3) | O4—C17—N1 | 118.8 (3) |
C2—C7—C8 | 106.0 (3) | O4—C17—C18 | 122.4 (3) |
C6—C7—C8 | 135.0 (3) | N1—C17—C18 | 118.8 (3) |
C1—C8—C7 | 105.4 (3) | C17—C18—H18A | 109.5 |
C1—C8—C9 | 126.8 (3) | C17—C18—H18B | 109.5 |
C7—C8—C9 | 127.7 (3) | H18A—C18—H18B | 109.5 |
O2—C9—C8 | 107.5 (3) | C17—C18—H18C | 109.5 |
O2—C9—C16 | 115.0 (3) | H18A—C18—H18C | 109.5 |
C8—C9—C16 | 113.9 (3) | H18B—C18—H18C | 109.5 |
O2—C9—C10 | 110.4 (3) | ||
C2—O1—C1—C8 | −0.2 (4) | C8—C9—C10—O3 | 68.1 (4) |
C1—O1—C2—C3 | 178.5 (4) | C16—C9—C10—O3 | −171.7 (3) |
C1—O1—C2—C7 | −0.3 (4) | O2—C9—C10—N1 | 129.8 (3) |
C7—C2—C3—C4 | −0.2 (6) | C8—C9—C10—N1 | −113.0 (3) |
O1—C2—C3—C4 | −178.8 (4) | C16—C9—C10—N1 | 7.2 (3) |
C2—C3—C4—C5 | −0.6 (6) | C17—N1—C11—C12 | 0.0 (5) |
C3—C4—C5—C6 | 0.9 (6) | C10—N1—C11—C12 | −175.9 (3) |
C4—C5—C6—C7 | −0.3 (6) | C17—N1—C11—C16 | 179.6 (3) |
C3—C2—C7—C6 | 0.7 (6) | C10—N1—C11—C16 | 3.7 (4) |
O1—C2—C7—C6 | 179.5 (3) | C16—C11—C12—C13 | −0.9 (5) |
C3—C2—C7—C8 | −178.2 (3) | N1—C11—C12—C13 | 178.7 (3) |
O1—C2—C7—C8 | 0.6 (4) | C11—C12—C13—C14 | 0.6 (6) |
C5—C6—C7—C2 | −0.4 (6) | C12—C13—C14—C15 | 0.9 (6) |
C5—C6—C7—C8 | 178.1 (4) | C13—C14—C15—C16 | −2.1 (5) |
O1—C1—C8—C7 | 0.6 (4) | C14—C15—C16—C11 | 1.8 (5) |
O1—C1—C8—C9 | −176.5 (3) | C14—C15—C16—C9 | −179.6 (3) |
C2—C7—C8—C1 | −0.7 (4) | C12—C11—C16—C15 | −0.3 (5) |
C6—C7—C8—C1 | −179.4 (4) | N1—C11—C16—C15 | 180.0 (3) |
C2—C7—C8—C9 | 176.3 (3) | C12—C11—C16—C9 | −179.1 (3) |
C6—C7—C8—C9 | −2.3 (7) | N1—C11—C16—C9 | 1.2 (4) |
C1—C8—C9—O2 | −139.7 (4) | O2—C9—C16—C15 | 56.8 (5) |
C7—C8—C9—O2 | 43.9 (4) | C8—C9—C16—C15 | −67.8 (5) |
C1—C8—C9—C16 | −11.1 (5) | C10—C9—C16—C15 | 176.3 (3) |
C7—C8—C9—C16 | 172.4 (3) | O2—C9—C16—C11 | −124.5 (3) |
C1—C8—C9—C10 | 101.3 (4) | C8—C9—C16—C11 | 110.9 (3) |
C7—C8—C9—C10 | −75.2 (4) | C10—C9—C16—C11 | −5.1 (3) |
C17—N1—C10—O3 | −3.9 (5) | C10—N1—C17—O4 | 168.1 (3) |
C11—N1—C10—O3 | 172.0 (3) | C11—N1—C17—O4 | −7.1 (5) |
C17—N1—C10—C9 | 177.3 (3) | C10—N1—C17—C18 | −12.1 (5) |
C11—N1—C10—C9 | −6.9 (3) | C11—N1—C17—C18 | 172.6 (3) |
O2—C9—C10—O3 | −49.0 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
C12—H12A···O4 | 0.93 | 2.30 | 2.841 (5) | 117 |
O2—H2A···O4i | 0.97 (4) | 1.98 (4) | 2.893 (4) | 155 (3) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C18H13NO4 |
Mr | 307.29 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 7.5900 (6), 9.6858 (8), 10.4040 (9) |
α, β, γ (°) | 74.141 (2), 83.650 (2), 78.772 (2) |
V (Å3) | 720.3 (1) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.36 × 0.24 × 0.18 |
Data collection | |
Diffractometer | Siemens SMART CCD area detector diffractometer |
Absorption correction | Empirical (using intensity measurements) SADABS (Sheldrick, 1996) |
Tmin, Tmax | 0.965, 0.982 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3999, 2421, 1233 |
Rint | 0.091 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.072, 0.174, 0.86 |
No. of reflections | 2421 |
No. of parameters | 214 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.30, −0.31 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXTL (Sheldrick, 1997), SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).
O1—C1 | 1.362 (4) | C1—C8 | 1.360 (5) |
O1—C2 | 1.385 (4) | C7—C8 | 1.450 (4) |
O2—C9 | 1.430 (4) | C8—C9 | 1.494 (5) |
N1—C17 | 1.411 (5) | C9—C16 | 1.502 (4) |
N1—C10 | 1.420 (4) | C9—C10 | 1.556 (5) |
O2—C9—C8 | 107.5 (3) | C8—C9—C10 | 107.9 (3) |
C10—N1—C17—C18 | −12.1 (5) | C11—N1—C17—C18 | 172.6 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C12—H12A···O4 | 0.93 | 2.30 | 2.841 (5) | 117 |
O2—H2A···O4i | 0.97 (4) | 1.98 (4) | 2.893 (4) | 155 (3) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
1H-indole-2,3-dione (isatin) derivatives have been of interest owing to their biological activities (Bieck et al., 1993), and their photo-induced reactions with alkenes giving the corresponding spirooxetanes have been investigated intensively (Xue et al., 2000). Our interest on the ring-opening reaction of such spirooxetane derivatives led us to the title compound (I) which was obtained by acid catalysed ring-opening reaction of a spiroxetane derivative. An X-ray crystallographic structure analysis of (I) was undertaken to confirm the 3-(heteroaryl)indole structure of this novel product.
The C9 atom is the chiral center atom of the title compound (I). The bond lengths and bond angles in the title compound (Table 1) show normal values (Allen et al., 1987). These values, especially those within the indole and benzofuran moieties, agree with those of the related structure previously studied (Usman et al., 2001). The indole moiety is almost planar with an angle of 2.3 (2)° between the pyrrolidine and benzene rings. The benzofuran moiety is also planar with an angle of 1.2 (2)° between the furan and benzene rings. The indole and benzofuran moieties make a dihedral angle of 75.3 (2)° between themselves corresponding to an equatorial configuration. The attached acetyl group at N1 atom makes a dihedral angle of 6.8 (2)° with the indole moiety.
In the title structure, the O4 atom of the acetyl group is involved in intra- and intermolecular hydrogen bonds. The intramolecular C—H···O interaction forms a six-membered closed ring of O4—C17—N1—C11—C12—H12A. The molecules are stacked into columns nearly along the c axis. The stronger intermolecular O—H···O interaction interconnects the O4 atoms with the hydrogen atom of the hydroxy group between the two molecules of the adjacent molecular columns. (see Table 2) This interaction as well as van der Waals interactions stabilize the molecular and packing structure in the crystal.