Literature DB >> 23468803

17-Hy-droxy-1,8-dimethyl-17-aza-penta-cyclo-[6.6.5.0(2,7).0(9,14).0(15,19)]nona-deca-2,4,6,9(14),10,12-hexa-ene-16,18-dione.

Barbara Miroslaw¹, Anna E Koziol, Magdalena Pakosinska-Parys, Marta Struga.

Abstract

In the title compound, C20H17NO3 (alternative name: N-hy-droxy-9,10-dimethyl-9,10-ethano-anthracene-11,12-dicarboximide), the rigid ethano-anthracene-dicarboximide moiety has a roof-shaped geometry, the inter-planar angle between the two terminal phenyl rings being 124.9 (6)°. In the crystal, mol-ecules are linked via O-H⋯O hydrogen bonds, forming chains along [010]. C-H⋯O and C-H⋯π inter-actions link adjacent chains, leading to the formation of a three-dimensional structure.

Entities: CellLine Chemical Disease Gene

Year: 2012 PMID： 23468803 PMCID： PMC3588838 DOI： 10.1107/S1600536812045151

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

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

C20H17NO3 M = 319.36 Monoclinic, a = 13.904 (1) Å b = 8.104 (1) Å c = 13.946 (1) Å β = 97.39 (1)° V = 1558.4 (3) Å3 Z = 4 Mo Kα radiation μ = 0.09 mm−1 T = 100 K 0.40 × 0.40 × 0.30 mm

Data collection

Oxford Diffraction Xcalibur (Sapphire2) diffractometer 5321 measured reflections 2827 independent reflections 2467 reflections with I > 2σ(I) R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.036 wR(F 2) = 0.096 S = 1.04 2827 reflections 223 parameters H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.30 e Å−3 Δρmin = −0.20 e Å−3 Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: 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. Click here for additional data file. Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812045151/bg2475sup1.cif Click here for additional data file. Supplementary material file. DOI: 10.1107/S1600536812045151/bg2475Isup2.mol Click here for additional data file. Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812045151/bg2475Isup3.hkl Click here for additional data file. Supplementary material file. DOI: 10.1107/S1600536812045151/bg2475Isup4.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₂₀H₁₇NO₃	F(000) = 672
M_r = 319.36	D_x = 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	R_int = 0.023
Graphite monochromator	θ_max = 25.2°, θ_min = 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(F_o²) + (0.0465P)² + 0.4721P] where P = (F_o² + 2F_c²)/3
2827 reflections	(Δ/σ)_max = 0.009
223 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

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	U_iso*/U_eq
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

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···O2^iv	0.95	2.54	3.457 (2)	163
C4—H4···Cg1^v	1.00	2.66	3.518 (3)	144
C10—H10···Cg2^vi	0.95	2.77	3.668 (3)	158

Table 1

Hydrogen-bond geometry (Å, °)

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⋯O2^iv	0.95	2.54	3.457 (2)	163
C4—H4⋯Cg1^v	1.00	2.66	3.518 (3)	144
C10—H10⋯Cg2^vi	0.95	2.77	3.668 (3)	158

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .

6 in total

1. The Cambridge Structural Database: a quarter of a million crystal structures and rising.

Authors: Frank H Allen
Journal: Acta Crystallogr B Date: 2002-05-29

2. A short history of SHELX.

Authors: George M Sheldrick
Journal: Acta Crystallogr A Date: 2007-12-21 Impact factor: 2.290

3. Anthracene based compounds as new L-type Ca2+ channel blockers: design, synthesis, and full biological profile.

Authors: Sergio Bova; Simona Saponara; Angela Rampa; Silvia Gobbi; Lorenzo Cima; Fabio Fusi; Giampietro Sgaragli; Maurizio Cavalli; Cristobal de los Rios; Jörg Striessnig; Alessandra Bisi
Journal: J Med Chem Date: 2009-03-12 Impact factor: 7.446

4. Synthesis of new N-substituted cyclic imides with an expected anxiolytic activity. XII. Derivatives of N-hydroxy-1,4-dimethyl-dibenzo[e.h]bicyclo[2.2.2]-octane-2,3-dicarboximide.

Authors: J Kossakowski; M Jarocka
Journal: Acta Pol Pharm Date: 2000-11 Impact factor: 0.330

5. Assembly of a self-complementary monomer: formation of supramolecular polymer networks and responsive gels.

Authors: Yong-Sheng Su; Jia-Wei Liu; Yi Jiang; Chuan-Feng Chen
Journal: Chemistry Date: 2011-01-17 Impact factor: 5.236

6. N-alkyl oxazolidines as stereocontrol elements in asymmetric Diels-Alder cycloadditions of 9-substituted anthracene derivatives.

Authors: Harry Adams; Ramadan A Bawa; Simon Jones
Journal: Org Biomol Chem Date: 2006-11-21 Impact factor: 3.876

6 in total