organic compounds
17-Hydroxy-1,8-dimethyl-17-azapentacyclo[6.6.5.02,7.09,14.015,19]nonadeca-2,4,6,9(14),10,12-hexaene-16,18-dione
aFaculty of Chemistry, Maria Curie-Sklodowska University, pl. M. Curie-Sklodowskiej 3, 20-031 Lublin, Poland, and bDepartment of Medical Chemistry, The Medical University, 02-007 Warsaw, Poland
*Correspondence e-mail: barbara.miroslaw@poczta.umcs.lublin.pl
In the title compound, C20H17NO3 (alternative name: N-hydroxy-9,10-dimethyl-9,10-ethanoanthracene-11,12-dicarboximide), the rigid ethanoanthracene-dicarboximide moiety has a roof-shaped geometry, the interplanar angle between the two terminal phenyl rings being 124.9 (6)°. In the crystal, molecules are linked via O—H⋯O hydrogen bonds, forming chains along [010]. C—H⋯O and C—H⋯π interactions link adjacent chains, leading to the formation of a three-dimensional structure.
Related literature
For the synthesis of the title compound, see: Kossakowski & Jarocka (2000). For the biological activity of related compounds, see: Bova et al. (2009). For related structures, see: Atherton & Jones (2002); Smet et al. (2000); Su et al. (2011), Guo et al. (2010); Adams et al. (2006); He & Ng (2007); Weber et al. (1991, 1994); Yang & Swager (1998). The rigid ethanoanthracenedicarboximide moiety of the title compound shows the typical roof-shaped geometry (Weber et al., 1991; Csöregh et al., 2003). For a description of the Cambridge Structural Database, see: Allen (2002).
Experimental
Crystal data
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Data collection
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Refinement
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Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: publCIF.
Supporting information
10.1107/S1600536812045151/bg2475sup1.cif
contains datablocks I, global. DOI:Supporting information file. DOI: 10.1107/S1600536812045151/bg2475Isup2.mol
Structure factors: contains datablock I. DOI: 10.1107/S1600536812045151/bg2475Isup3.hkl
Supporting information file. DOI: 10.1107/S1600536812045151/bg2475Isup4.cml
The title compound, UPAC name: 17-hydroxy-1,8-dimethyl-17-azapentacyclo[6.6.5.02,7.09,14.015,19]nonadeca-2,4,6,9(14),10,12-hexaene-16,18-dione, was synthesized in the search of compounds with potential anxiolytic activity, as described previously (Kossakowski & Jarocka, 2000).
All C-bonded H atoms were positioned geometrically and allowed to ride on the attached atom with the C—H bond lengths of 0.95 Å for aromatic atoms, 1.00 Å for methine and 0.98 Å for methyl groups. Uiso(H) values were fixed to 1.2Ueq(C) and 1.5Ueq(Cmethyl). The hydroxyl H atom was located in the difference
and refined isotropically.Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell
CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: publCIF.Fig. 1. Ortep view of the title compound with atom numbering scheme. Ellipsoids for non-hydrogen atoms were drawn at the 50 % probability level. | |
Fig. 2. Linear association of molecules in crystal of 1 through the O–H···O hydrogen bonds and C–H···π interactions between adjacent chains. The Cg2 refers to the center of gravity between atoms C15/C16. Symmetry codes: (i) –x+1/2, y–1/2, –z+3/2; (vi) –x+1/2, y–1/2, –z+1/2. | |
Fig. 3. C–H···O and C–H···π interactions in crystal of 1 with short C15···C15iii intermolecular contact (3.386 (2) Å). The Cg2 is the centroid of the C15/C16 bond. Symmetry codes: (iii) –x+1, –y+1, –z+1; (vi) –x+1/2, y–1/2, –z+1/2. | |
Fig. 4. C–H···O hydrogen bonds and C–H···π interactions in crystal of 1. The Cg1 refers to the centroid of the C6–C11 ring. Symmetry codes: (iv) x, y+1, z; (v) –x, –y+1, –z+1. |
C20H17NO3 | F(000) = 672 |
Mr = 319.36 | Dx = 1.361 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 3666 reflections |
a = 13.904 (1) Å | θ = 2.9–29.8° |
b = 8.104 (1) Å | µ = 0.09 mm−1 |
c = 13.946 (1) Å | T = 100 K |
β = 97.39 (1)° | Prism, colourless |
V = 1558.4 (3) Å3 | 0.40 × 0.40 × 0.30 mm |
Z = 4 |
Oxford Diffraction Xcalibur (Sapphire2) diffractometer | 2467 reflections with I > 2σ(I) |
Radiation source: Enhance (Mo) X-ray Source | Rint = 0.023 |
Graphite monochromator | θmax = 25.2°, θmin = 2.9° |
Detector resolution: 8.4221 pixels mm-1 | h = −16→16 |
ω scans | k = −9→6 |
5321 measured reflections | l = −9→16 |
2827 independent reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.036 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.096 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0465P)2 + 0.4721P] where P = (Fo2 + 2Fc2)/3 |
2827 reflections | (Δ/σ)max = 0.009 |
223 parameters | Δρmax = 0.30 e Å−3 |
0 restraints | Δρmin = −0.20 e Å−3 |
C20H17NO3 | V = 1558.4 (3) Å3 |
Mr = 319.36 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 13.904 (1) Å | µ = 0.09 mm−1 |
b = 8.104 (1) Å | T = 100 K |
c = 13.946 (1) Å | 0.40 × 0.40 × 0.30 mm |
β = 97.39 (1)° |
Oxford Diffraction Xcalibur (Sapphire2) diffractometer | 2467 reflections with I > 2σ(I) |
5321 measured reflections | Rint = 0.023 |
2827 independent reflections |
R[F2 > 2σ(F2)] = 0.036 | 0 restraints |
wR(F2) = 0.096 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | Δρmax = 0.30 e Å−3 |
2827 reflections | Δρmin = −0.20 e Å−3 |
223 parameters |
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.28230 (8) | 0.37858 (13) | 0.63969 (8) | 0.0154 (3) | |
O1 | 0.23524 (7) | 0.61166 (12) | 0.71225 (6) | 0.0201 (2) | |
O2 | 0.30265 (7) | 0.15262 (11) | 0.54480 (7) | 0.0217 (2) | |
O3 | 0.36001 (7) | 0.34569 (12) | 0.70937 (7) | 0.0194 (2) | |
H3A | 0.3338 (15) | 0.258 (3) | 0.7443 (15) | 0.049 (6)* | |
C1 | 0.22513 (9) | 0.51497 (16) | 0.64443 (9) | 0.0148 (3) | |
C2 | 0.25875 (10) | 0.27735 (16) | 0.55890 (9) | 0.0161 (3) | |
C3 | 0.17056 (9) | 0.35563 (16) | 0.49956 (9) | 0.0151 (3) | |
H3 | 0.1129 | 0.2818 | 0.4999 | 0.018* | |
C4 | 0.15350 (9) | 0.51968 (15) | 0.55294 (9) | 0.0147 (3) | |
H4 | 0.0859 | 0.5217 | 0.5702 | 0.018* | |
C5 | 0.16945 (10) | 0.67321 (16) | 0.48659 (9) | 0.0157 (3) | |
C6 | 0.09511 (9) | 0.64834 (16) | 0.39688 (9) | 0.0161 (3) | |
C7 | 0.02301 (10) | 0.76017 (17) | 0.36135 (10) | 0.0199 (3) | |
H7 | 0.0172 | 0.8623 | 0.3936 | 0.024* | |
C8 | −0.04079 (10) | 0.72243 (19) | 0.27836 (11) | 0.0242 (3) | |
H8 | −0.0894 | 0.7994 | 0.2538 | 0.029* | |
C9 | −0.03310 (10) | 0.5725 (2) | 0.23190 (10) | 0.0252 (3) | |
H9 | −0.0771 | 0.5464 | 0.1761 | 0.030* | |
C10 | 0.03931 (10) | 0.45948 (19) | 0.26700 (10) | 0.0216 (3) | |
H10 | 0.0442 | 0.3568 | 0.2351 | 0.026* | |
C11 | 0.10405 (9) | 0.49792 (17) | 0.34867 (9) | 0.0172 (3) | |
C12 | 0.18898 (10) | 0.38987 (16) | 0.39219 (9) | 0.0167 (3) | |
C13 | 0.27923 (10) | 0.49978 (16) | 0.40301 (9) | 0.0159 (3) | |
C14 | 0.36774 (10) | 0.45997 (18) | 0.37202 (10) | 0.0206 (3) | |
H14 | 0.3746 | 0.3601 | 0.3379 | 0.025* | |
C15 | 0.44605 (10) | 0.56721 (19) | 0.39128 (10) | 0.0253 (3) | |
H15 | 0.5065 | 0.5400 | 0.3704 | 0.030* | |
C16 | 0.43639 (10) | 0.71368 (19) | 0.44081 (10) | 0.0239 (3) | |
H16 | 0.4903 | 0.7861 | 0.4534 | 0.029* | |
C17 | 0.34813 (10) | 0.75541 (17) | 0.47223 (10) | 0.0195 (3) | |
H17 | 0.3417 | 0.8559 | 0.5059 | 0.023* | |
C18 | 0.26956 (10) | 0.64801 (16) | 0.45364 (9) | 0.0159 (3) | |
C19 | 0.15742 (11) | 0.83661 (16) | 0.53834 (10) | 0.0207 (3) | |
H19A | 0.0939 | 0.8391 | 0.5618 | 0.031* | |
H19B | 0.1619 | 0.9282 | 0.4932 | 0.031* | |
H19C | 0.2087 | 0.8474 | 0.5932 | 0.031* | |
C20 | 0.19871 (11) | 0.22982 (17) | 0.33594 (10) | 0.0230 (3) | |
H20A | 0.2102 | 0.2562 | 0.2698 | 0.034* | |
H20B | 0.1389 | 0.1654 | 0.3342 | 0.034* | |
H20C | 0.2533 | 0.1654 | 0.3678 | 0.034* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0145 (6) | 0.0179 (6) | 0.0133 (5) | −0.0008 (4) | 0.0005 (4) | 0.0025 (4) |
O1 | 0.0195 (5) | 0.0236 (5) | 0.0173 (5) | −0.0011 (4) | 0.0024 (4) | −0.0065 (4) |
O2 | 0.0259 (6) | 0.0150 (5) | 0.0245 (5) | 0.0039 (4) | 0.0045 (4) | 0.0008 (4) |
O3 | 0.0143 (5) | 0.0250 (5) | 0.0176 (5) | −0.0010 (4) | −0.0024 (4) | 0.0058 (4) |
C1 | 0.0129 (6) | 0.0164 (7) | 0.0159 (7) | −0.0034 (5) | 0.0058 (5) | 0.0010 (5) |
C2 | 0.0182 (7) | 0.0144 (7) | 0.0167 (7) | −0.0036 (5) | 0.0062 (5) | 0.0021 (5) |
C3 | 0.0149 (6) | 0.0152 (7) | 0.0154 (7) | −0.0028 (5) | 0.0032 (5) | −0.0006 (5) |
C4 | 0.0130 (6) | 0.0160 (6) | 0.0155 (7) | −0.0015 (5) | 0.0031 (5) | −0.0010 (5) |
C5 | 0.0154 (7) | 0.0153 (7) | 0.0166 (7) | −0.0006 (5) | 0.0026 (5) | 0.0010 (5) |
C6 | 0.0141 (7) | 0.0190 (7) | 0.0158 (7) | −0.0024 (5) | 0.0049 (5) | 0.0024 (5) |
C7 | 0.0173 (7) | 0.0193 (7) | 0.0242 (8) | 0.0006 (5) | 0.0067 (6) | 0.0055 (6) |
C8 | 0.0158 (7) | 0.0310 (8) | 0.0261 (8) | 0.0008 (6) | 0.0034 (6) | 0.0126 (6) |
C9 | 0.0193 (7) | 0.0376 (9) | 0.0177 (7) | −0.0065 (6) | −0.0011 (6) | 0.0059 (6) |
C10 | 0.0202 (7) | 0.0280 (8) | 0.0168 (7) | −0.0038 (6) | 0.0026 (5) | −0.0007 (6) |
C11 | 0.0167 (7) | 0.0207 (7) | 0.0149 (7) | −0.0026 (5) | 0.0048 (5) | 0.0019 (5) |
C12 | 0.0187 (7) | 0.0187 (7) | 0.0130 (6) | −0.0008 (5) | 0.0028 (5) | −0.0005 (5) |
C13 | 0.0172 (7) | 0.0194 (7) | 0.0110 (6) | 0.0013 (5) | 0.0015 (5) | 0.0048 (5) |
C14 | 0.0218 (7) | 0.0233 (7) | 0.0179 (7) | 0.0056 (6) | 0.0072 (6) | 0.0054 (6) |
C15 | 0.0170 (7) | 0.0350 (9) | 0.0251 (8) | 0.0061 (6) | 0.0079 (6) | 0.0138 (7) |
C16 | 0.0159 (7) | 0.0310 (8) | 0.0242 (8) | −0.0048 (6) | 0.0005 (6) | 0.0118 (6) |
C17 | 0.0198 (7) | 0.0206 (7) | 0.0175 (7) | −0.0030 (6) | −0.0003 (5) | 0.0055 (6) |
C18 | 0.0158 (7) | 0.0189 (7) | 0.0127 (6) | 0.0011 (5) | 0.0012 (5) | 0.0051 (5) |
C19 | 0.0229 (7) | 0.0174 (7) | 0.0223 (7) | 0.0001 (6) | 0.0046 (6) | −0.0011 (6) |
C20 | 0.0292 (8) | 0.0219 (7) | 0.0181 (7) | 0.0003 (6) | 0.0039 (6) | −0.0034 (6) |
N1—C1 | 1.3679 (17) | C9—H9 | 0.9500 |
N1—O3 | 1.3831 (14) | C10—C11 | 1.3933 (19) |
N1—C2 | 1.3981 (17) | C10—H10 | 0.9500 |
O1—C1 | 1.2223 (16) | C11—C12 | 1.5314 (19) |
O2—C2 | 1.2099 (16) | C12—C13 | 1.5304 (19) |
O3—H3A | 0.96 (2) | C12—C20 | 1.5308 (19) |
C1—C4 | 1.5149 (18) | C13—C14 | 1.3936 (19) |
C2—C3 | 1.5264 (18) | C13—C18 | 1.4085 (18) |
C3—C4 | 1.5567 (17) | C14—C15 | 1.392 (2) |
C3—C12 | 1.5758 (18) | C14—H14 | 0.9500 |
C3—H3 | 1.0000 | C15—C16 | 1.388 (2) |
C4—C5 | 1.5831 (18) | C15—H15 | 0.9500 |
C4—H4 | 1.0000 | C16—C17 | 1.397 (2) |
C5—C19 | 1.5275 (18) | C16—H16 | 0.9500 |
C5—C6 | 1.5303 (18) | C17—C18 | 1.3948 (19) |
C5—C18 | 1.5345 (18) | C17—H17 | 0.9500 |
C6—C7 | 1.3944 (19) | C19—H19A | 0.9800 |
C6—C11 | 1.4053 (19) | C19—H19B | 0.9800 |
C7—C8 | 1.399 (2) | C19—H19C | 0.9800 |
C7—H7 | 0.9500 | C20—H20A | 0.9800 |
C8—C9 | 1.387 (2) | C20—H20B | 0.9800 |
C8—H8 | 0.9500 | C20—H20C | 0.9800 |
C9—C10 | 1.402 (2) | ||
C1—N1—O3 | 121.87 (10) | C11—C10—H10 | 120.0 |
C1—N1—C2 | 115.83 (11) | C9—C10—H10 | 120.0 |
O3—N1—C2 | 122.27 (11) | C10—C11—C6 | 119.83 (12) |
N1—O3—H3A | 100.7 (12) | C10—C11—C12 | 125.48 (12) |
O1—C1—N1 | 123.07 (12) | C6—C11—C12 | 114.68 (11) |
O1—C1—C4 | 129.30 (12) | C13—C12—C20 | 114.73 (11) |
N1—C1—C4 | 107.62 (11) | C13—C12—C11 | 106.67 (11) |
O2—C2—N1 | 123.39 (12) | C20—C12—C11 | 113.32 (11) |
O2—C2—C3 | 130.24 (12) | C13—C12—C3 | 103.89 (10) |
N1—C2—C3 | 106.36 (11) | C20—C12—C3 | 111.94 (11) |
C2—C3—C4 | 104.88 (10) | C11—C12—C3 | 105.43 (10) |
C2—C3—C12 | 111.78 (11) | C14—C13—C18 | 119.86 (13) |
C4—C3—C12 | 110.94 (10) | C14—C13—C12 | 125.47 (12) |
C2—C3—H3 | 109.7 | C18—C13—C12 | 114.58 (11) |
C4—C3—H3 | 109.7 | C15—C14—C13 | 119.71 (13) |
C12—C3—H3 | 109.7 | C15—C14—H14 | 120.1 |
C1—C4—C3 | 104.90 (10) | C13—C14—H14 | 120.1 |
C1—C4—C5 | 112.69 (10) | C16—C15—C14 | 120.43 (13) |
C3—C4—C5 | 110.51 (10) | C16—C15—H15 | 119.8 |
C1—C4—H4 | 109.5 | C14—C15—H15 | 119.8 |
C3—C4—H4 | 109.5 | C15—C16—C17 | 120.54 (13) |
C5—C4—H4 | 109.5 | C15—C16—H16 | 119.7 |
C19—C5—C6 | 113.39 (11) | C17—C16—H16 | 119.7 |
C19—C5—C18 | 114.55 (11) | C18—C17—C16 | 119.30 (13) |
C6—C5—C18 | 106.32 (10) | C18—C17—H17 | 120.3 |
C19—C5—C4 | 111.91 (10) | C16—C17—H17 | 120.3 |
C6—C5—C4 | 104.10 (10) | C17—C18—C13 | 120.16 (12) |
C18—C5—C4 | 105.72 (10) | C17—C18—C5 | 125.47 (12) |
C7—C6—C11 | 119.84 (12) | C13—C18—C5 | 114.35 (11) |
C7—C6—C5 | 125.74 (12) | C5—C19—H19A | 109.5 |
C11—C6—C5 | 114.42 (11) | C5—C19—H19B | 109.5 |
C6—C7—C8 | 120.17 (13) | H19A—C19—H19B | 109.5 |
C6—C7—H7 | 119.9 | C5—C19—H19C | 109.5 |
C8—C7—H7 | 119.9 | H19A—C19—H19C | 109.5 |
C9—C8—C7 | 119.95 (13) | H19B—C19—H19C | 109.5 |
C9—C8—H8 | 120.0 | C12—C20—H20A | 109.5 |
C7—C8—H8 | 120.0 | C12—C20—H20B | 109.5 |
C8—C9—C10 | 120.27 (13) | H20A—C20—H20B | 109.5 |
C8—C9—H9 | 119.9 | C12—C20—H20C | 109.5 |
C10—C9—H9 | 119.9 | H20A—C20—H20C | 109.5 |
C11—C10—C9 | 119.92 (14) | H20B—C20—H20C | 109.5 |
Cg1 is the centroid of the C6–C11 ring. Cg2 refers to the mid-point of the C15—C16 bond. |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3A···O1i | 0.96 (2) | 1.69 (2) | 2.630 (1) | 167 (2) |
C8—H8···O1ii | 0.95 | 2.54 | 3.408 (2) | 152 |
C15—H15···O3iii | 0.95 | 2.46 | 3.273 (2) | 143 |
C17—H17···O2iv | 0.95 | 2.54 | 3.457 (2) | 163 |
C4—H4···Cg1v | 1.00 | 2.66 | 3.518 (3) | 144 |
C10—H10···Cg2vi | 0.95 | 2.77 | 3.668 (3) | 158 |
Symmetry codes: (i) −x+1/2, y−1/2, −z+3/2; (ii) x−1/2, −y+3/2, z−1/2; (iii) −x+1, −y+1, −z+1; (iv) x, y+1, z; (v) −x, −y+1, −z+1; (vi) −x+1/2, y−1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C20H17NO3 |
Mr | 319.36 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 100 |
a, b, c (Å) | 13.904 (1), 8.104 (1), 13.946 (1) |
β (°) | 97.39 (1) |
V (Å3) | 1558.4 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.40 × 0.40 × 0.30 |
Data collection | |
Diffractometer | Oxford Diffraction Xcalibur (Sapphire2) diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5321, 2827, 2467 |
Rint | 0.023 |
(sin θ/λ)max (Å−1) | 0.600 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.036, 0.096, 1.04 |
No. of reflections | 2827 |
No. of parameters | 223 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.30, −0.20 |
Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), publCIF.
Cg1 is the centroid of the C6–C11 ring. Cg2 refers to the mid-point of the C15—C16 bond. |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3A···O1i | 0.96 (2) | 1.69 (2) | 2.630 (1) | 167 (2) |
C8—H8···O1ii | 0.95 | 2.54 | 3.408 (2) | 152 |
C15—H15···O3iii | 0.95 | 2.46 | 3.273 (2) | 143 |
C17—H17···O2iv | 0.95 | 2.54 | 3.457 (2) | 163 |
C4—H4···Cg1v | 1.00 | 2.66 | 3.518 (3) | 144 |
C10—H10···Cg2vi | 0.95 | 2.77 | 3.668 (3) | 158 |
Symmetry codes: (i) −x+1/2, y−1/2, −z+3/2; (ii) x−1/2, −y+3/2, z−1/2; (iii) −x+1, −y+1, −z+1; (iv) x, y+1, z; (v) −x, −y+1, −z+1; (vi) −x+1/2, y−1/2, −z+1/2. |
References
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Roof-shaped aromatic hydrocarbon derivatives have been used for inclusion of neutral compounds (Weber et al., 1991; 1994) and as porous polymer films and sensors for dinitrotoluene with possible application as a land mine detectors (Yang & Swager, 1998). The N-substitution is the most common way of modification of these molecules (Weber et al., 1994; Smet et al., 2000). Some experiments were also conducted on the substitution in the aryl moiety (Atherton & Jones, 2002; Adams et al., 2006; He & Ng, 2007). The search of the CSD (CSD v5.33 and updates; Allen, 2002) revealed 67 crystal structures of compounds with the rigid pentacyclic 9,10-ethanoanthracenedicarboximide skeleton. However, none of these derivatives has N-hydroxy substituent and only two molecules are symmetrically substituted at bridgehead C atoms (here C5, C12; see Fig. 1). In these crystals the polycyclic skeletons are combined with voluminous macrocyclic fragments. (Su et al., 2011; Guo et al., 2010). The rigid ethanoanthracenedicarboximide moiety of the title compound (Fig. 1) shows the typical roof-shaped geometry (Weber et al., 1991; Csöregh et al., 2003); the interplanar angle between the two terminal phenyl rings is 124.9 °. The hydroxyl O atom interacts through the O3–H···O1 hydrogen bond (Fig. 2). Molecules form chains along the 21 screw axis. Between adjacent chains many C–H···O and C–H···π interactions are observed (Figs. 2–4, Table 1).