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ISSN: 2056-9890

Spiro­[indene-1,1′-benzo[e]indolin]-2′-one

aSchool of Pharmaceutical Science, Southern Medical University, Guangzhou 510515, People's Republic of China
*Correspondence e-mail: jxchen6281@gmail.com

(Received 28 October 2010; accepted 29 November 2010; online 4 December 2010)

In the title compound, C20H13NO, the indene ring is disordered over two sites with an occupancy ratio of 0.557 (2):0.443 (2). Both disordered components of indene are nearly perpendicular to the naphthalene ring system, making dihedral angles of 90.9 (2) and 85.0 (5)°. The five-membered ring of the 1H-pyrrol-2(3H)-one adopts an envelope conformation with the spiro C atom at the flap position. Inter­molecular classical N—H⋯O and weak C—H⋯O hydrogen bonding is present in the crystal structure.

Related literature

For the biological activity of spiro lacta­ms, see: Tsuda et al. (2004[Tsuda, M., Kasai, Y. & Komatsu, K. (2004). Org. Lett. 6, 3087-3089.]); Chen et al. (2005[Chen, Z.-P., Tan, D.-M., Su, C.-Y. & Xu, Z.-L. (2005). Acta Cryst. E61, o1308-o1309.]). For the synthesis of the title compound, see: Ready et al. (2004[Ready, J. M., Reisman, S. E. & Hirata, M. (2004). Angew. Chem. Int. Ed. 43, 1270-1273.]); Schoemaker & Speckamp (1978[Schoemaker, H. E. & Speckamp, W. N. (1978). Tetrahedron Lett. 19, 1515-1518.]).

[Scheme 1]

Experimental

Crystal data
  • C20H13NO

  • Mr = 283.31

  • Monoclinic, P 21 /c

  • a = 13.0150 (18) Å

  • b = 7.9180 (11) Å

  • c = 15.537 (2) Å

  • β = 112.030 (2)°

  • V = 1484.2 (4) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 293 K

  • 0.50 × 0.41 × 0.33 mm

Data collection
  • Rigaku Mercury diffractometer

  • 6913 measured reflections

  • 2526 independent reflections

  • 1984 reflections with I > 2σ(I)

  • Rint = 0.025

Refinement
  • R[F2 > 2σ(F2)] = 0.074

  • wR(F2) = 0.199

  • S = 1.06

  • 2526 reflections

  • 203 parameters

  • 30 restraints

  • H-atom parameters constrained

  • Δρmax = 0.23 e Å−3

  • Δρmin = −0.27 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1A⋯O1i 0.86 1.99 2.815 (3) 162
C18—H18A⋯O1ii 0.93 2.35 3.064 (5) 133
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: CrystalClear (Rigaku/MSC, 2001[Rigaku/MSC (2001). CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA.]); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2004[Rigaku/MSC, (2004). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEPII (Johnson, 1976[Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

In the past decades, spiro lactams have been attracted considerable interest because they are commonly found as subunits of many natural products. Some of them have significant biological activities, including multiple drug resistance reversing, antifungal and antitumor activities (Tsuda et al.,2004). Synthetic methods directed to these classes of spiro lactam compounds have been developed (Ready et al., 2004). Among them, spiro cyclizations of N-acyliminium ions with an internalalkene nucleophile were first described by Speckamp (Schoemaker et al., 1978). Reductive coupling of acrylates with isocyanates to furnish spiro lactam skeleton was used by Wood [Ready et al., 2004]. The title compound I was synthesized in one step through a new ring-rearrangement reaction. It was undertaken as a continuation of our efforts towards synthesis of dibenzoxanthenes which exhibit a wide variety of biological activities [Chen et al., 2005].

The asymmetric unit of I contains one independent spiro-[indene-1,3'-(2',3'-dihydro-2'-oxa-benzo[e]indole)] molecule. In the complex I, the naphthyl ring and indene ring are almost perpendicular to each other, making a diheral angle of 90.9 (2)°. All bond lengths and bond angles are in the normal ranges and comparable to those observed in the similar substituted spiro-[indene-1,3'-(2',3'-dihydro-2'-oxa-benzo[e]indole)], except the disordered part of indene ring. The C(11)=O(1) bond length of 1.215 (4) Å of oxa-indole moiety conforms to the value for a double bond.

In the crystal of I, there are two types hydrogen bonding interactions: one type is classical hydrogen bonding between O(1) atom and N(1) atom from oxa-benzo[e]indole moiety, the other one is unclassical hydrogen bonding between O(1) atom and C(18) atom from the phenyl group. The molecule I was linked together by a double strong classical intermolecular hydrogen bonds of N(1)—H1A···O(1), thereby forming a dimer structure, while the dimers were futher linked by the unclassical hydrogen bonds of C(18)—HA···O(1), thereby forming a two dimessional network structure.

Related literature top

For the biological activity of spiro lactames, see: Tsuda et al. (2004); Chen et al. (2005). For the synthesis of the title compound, see: Ready et al. (2004); Schoemaker & Speckamp (1978).

Experimental top

Into a stirred solution of CuCl2.2H2O (17 mg, 0.1 mmol) in methanol (5 ml) was added a solution of ethanolamine (6 mg, 0.1 mmol) in methanol (2 ml). After 10 min. a solution of 2-amino-2'-hydroxy-1,1'-binaphthyl (0.1 mmol) in methanol (2 ml) was added and the reaction mixture was stirred at 323 K. When the reaction was completed, the solvent was removed under reduced pressure. The residue was extracted with AcOEt (10 ml), washed with 5% ammonia (10 ml) and water (10 ml), then dried with Na2SO4, and the solvent was removed under reduced pressure. Thick layer chromatography of the residue (hexane:ethyl acetate, 10:1) followed by recrystallization from acetone gave the title complex as red crystals. Yield: ca 82%.

Refinement top

The indene ring was found to be disordered over two sites, occupancies were refined to 0.557 (2):0.443 (2). The distance restraints have been used to make these two disordered indene ring with same bond lengths and same displacement parameters. H atoms were positioned geometrically with N—H = 0.86 and C—H = 0.93 Å, and refined using riding-model approximation with Uiso(H) = 1.2Ueq(C,N).

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2001); cell refinement: CrystalClear (Rigaku/MSC, 2001); data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The dimer structure formed via N—H···O hydrogen bonding interactions in 1, shown as dashed lines. Symmetry transformations used to generate equivalent atoms: A: -x + 1, -y + 1, -z + 1. Hydrogen atoms are drawn as spheres of arbitrary radii.
[Figure 2] Fig. 2. The two dimensional network structure along bc plane formed via N—H···O and C—H···O hydrogen bonding interactions in I, shown as dashed lines, Symmetry transformations used to generate equivalent atoms: A: -x + 1, -y + 1, -z + 1, B: -x + 1, y + 1/2, -z + 1/2, C: -x + 1, y - 1/2, -z + 1/2.
Spiro[indene-1,1'-benzo[e]indolin]-2'-one top
Crystal data top
C20H13NOF(000) = 592
Mr = 283.31Dx = 1.268 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5963 reflections
a = 13.0150 (18) Åθ = 2.8–25.3°
b = 7.9180 (11) ŵ = 0.08 mm1
c = 15.537 (2) ÅT = 293 K
β = 112.030 (2)°Block, red
V = 1484.2 (4) Å30.50 × 0.41 × 0.33 mm
Z = 4
Data collection top
Rigaku Mercury
diffractometer
1984 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.025
Graphite monochromatorθmax = 24.7°, θmin = 1.7°
Detector resolution: 10.0 pixels mm-1h = 1515
ω scansk = 99
6913 measured reflectionsl = 1218
2526 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.074Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.199H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0672P)2 + 1.1136P]
where P = (Fo2 + 2Fc2)/3
2526 reflections(Δ/σ)max < 0.001
203 parametersΔρmax = 0.23 e Å3
30 restraintsΔρmin = 0.27 e Å3
Crystal data top
C20H13NOV = 1484.2 (4) Å3
Mr = 283.31Z = 4
Monoclinic, P21/cMo Kα radiation
a = 13.0150 (18) ŵ = 0.08 mm1
b = 7.9180 (11) ÅT = 293 K
c = 15.537 (2) Å0.50 × 0.41 × 0.33 mm
β = 112.030 (2)°
Data collection top
Rigaku Mercury
diffractometer
1984 reflections with I > 2σ(I)
6913 measured reflectionsRint = 0.025
2526 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.07430 restraints
wR(F2) = 0.199H-atom parameters constrained
S = 1.06Δρmax = 0.23 e Å3
2526 reflectionsΔρmin = 0.27 e Å3
203 parameters
Special details top

Experimental. 1H NMR (CDCl3, 500 MHz) 8.63 (s, 1H), 7.83 (d, 1H, J = 8.5 Hz), 7.77 (d, 1H, J = 8.0 Hz), 7.56 (d, 1H, J = 7.5 Hz), 7.36 (t, 1H, J = 7.5 and 8.0 Hz), 7.32 (d, 1H, J = 5.5 Hz), 7.29 (d, 1H, J = 9.0 Hz), 7.23 (t, 1H, J =), 7.15 (t, 1H, J =), 7.11 (t, 1H, J =), 6.98 (d, 1H, J = 7.5 Hz), 6.77 (d, 1H, J = 8.5 Hz), 6.45 (d, 1H, J = 5.5 Hz); IR (KBr, cm-1) 3390, 3170, 3075, 2926, 1711, 1627, 1580, 1521, 1456, 1353, 1297, 1223, 814, 765, 744; Anal. C20H13ON, Calcd: C, 84.78, H, 4.62, N, 4.94, Found: C, 84.57, H, 4.65, N, 4.56.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.4788 (3)0.6054 (4)0.39578 (16)0.1336 (14)
N10.3680 (2)0.4050 (3)0.41956 (16)0.0717 (8)
H1A0.40270.39120.47830.086*
C10.2722 (2)0.3164 (4)0.36566 (19)0.0597 (7)
C20.2175 (3)0.1940 (5)0.3960 (2)0.0783 (10)
H2A0.24230.16250.45810.094*
C30.1266 (3)0.1220 (5)0.3317 (3)0.0884 (11)
H3A0.08900.03900.35050.106*
C40.0870 (2)0.1683 (4)0.2374 (2)0.0668 (8)
C50.0063 (3)0.0902 (5)0.1699 (3)0.0896 (11)
H5A0.04410.00670.18830.108*
C60.0415 (3)0.1341 (5)0.0798 (3)0.0924 (12)
H6A0.10300.08090.03670.111*
C70.0134 (3)0.2581 (5)0.0508 (2)0.0858 (11)
H7A0.01170.28780.01160.103*
C80.1034 (3)0.3363 (5)0.1127 (2)0.0793 (10)
H8A0.13950.41930.09230.095*
C90.1431 (2)0.2935 (4)0.20776 (19)0.0588 (7)
C100.2377 (3)0.3660 (4)0.2759 (2)0.0650 (8)
C110.3982 (3)0.5138 (6)0.3676 (2)0.1029 (15)
C120.2951 (3)0.5332 (5)0.2738 (3)0.0514 (10)0.557 (2)
C130.2283 (5)0.6974 (6)0.2556 (4)0.0639 (12)0.557 (2)
H130.18590.73160.28920.077*0.557 (2)
C140.2377 (5)0.7833 (9)0.1879 (5)0.0750 (17)0.557 (2)
H140.20400.88680.16660.090*0.557 (2)
C150.3094 (3)0.6930 (4)0.1504 (3)0.0611 (11)0.557 (2)
C160.3462 (4)0.7337 (5)0.0797 (3)0.0827 (14)0.557 (2)
H16A0.32420.83450.04730.099*0.557 (2)
C170.4157 (4)0.6237 (6)0.0575 (3)0.0898 (15)0.557 (2)
H17A0.44030.65090.01030.108*0.557 (2)
C180.4485 (4)0.4729 (5)0.1060 (3)0.0853 (15)0.557 (2)
H18A0.49510.39930.09110.102*0.557 (2)
C190.4118 (4)0.4322 (4)0.1766 (3)0.068 (2)0.557 (2)
H19A0.43370.33140.20900.082*0.557 (2)
C200.3422 (3)0.5422 (5)0.1988 (2)0.0552 (13)0.557 (2)
C12'0.3404 (4)0.4514 (6)0.2642 (3)0.0514 (10)0.443 (2)
C13'0.4061 (6)0.3612 (10)0.2125 (5)0.0639 (12)0.443 (2)
H13'0.43120.25030.22340.077*0.443 (2)
C14'0.4215 (9)0.4607 (11)0.1519 (9)0.0750 (17)0.443 (2)
H14'0.46290.43230.11660.090*0.443 (2)
C15'0.3656 (4)0.6226 (5)0.1461 (3)0.0611 (11)0.443 (2)
C16'0.3591 (5)0.7675 (7)0.0938 (4)0.0827 (14)0.443 (2)
H16B0.39140.76950.04960.099*0.443 (2)
C17'0.3042 (5)0.9094 (6)0.1075 (4)0.0898 (15)0.443 (2)
H17B0.29991.00640.07260.108*0.443 (2)
C18'0.2559 (5)0.9064 (5)0.1735 (4)0.0853 (15)0.443 (2)
H18B0.21921.00140.18270.102*0.443 (2)
C19'0.2624 (5)0.7615 (6)0.2258 (4)0.068 (2)0.443 (2)
H19B0.23000.75950.26990.082*0.443 (2)
C20'0.3172 (4)0.6196 (5)0.2121 (3)0.0552 (13)0.443 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.148 (3)0.160 (3)0.0576 (14)0.098 (2)0.0021 (15)0.0137 (16)
N10.0810 (17)0.0797 (18)0.0457 (13)0.0173 (14)0.0138 (12)0.0037 (12)
C10.0646 (17)0.0605 (17)0.0530 (16)0.0034 (14)0.0209 (13)0.0001 (13)
C20.086 (2)0.089 (2)0.0617 (18)0.014 (2)0.0297 (17)0.0139 (17)
C30.087 (2)0.098 (3)0.084 (2)0.028 (2)0.035 (2)0.011 (2)
C40.0625 (18)0.0687 (19)0.0719 (19)0.0075 (15)0.0283 (15)0.0021 (16)
C50.070 (2)0.099 (3)0.095 (3)0.027 (2)0.025 (2)0.006 (2)
C60.069 (2)0.103 (3)0.090 (3)0.020 (2)0.0126 (19)0.017 (2)
C70.082 (2)0.096 (3)0.063 (2)0.011 (2)0.0097 (17)0.0075 (19)
C80.083 (2)0.084 (2)0.0570 (18)0.0210 (19)0.0111 (16)0.0028 (17)
C90.0600 (16)0.0561 (16)0.0582 (16)0.0027 (14)0.0196 (13)0.0016 (13)
C100.0726 (19)0.0625 (18)0.0535 (16)0.0158 (15)0.0164 (14)0.0031 (14)
C110.120 (3)0.116 (3)0.0517 (18)0.067 (3)0.0086 (19)0.0065 (19)
C120.057 (3)0.046 (2)0.0506 (19)0.0010 (17)0.0190 (18)0.0007 (19)
C130.061 (3)0.055 (3)0.078 (3)0.000 (2)0.028 (2)0.006 (2)
C140.064 (3)0.071 (4)0.084 (4)0.003 (3)0.022 (3)0.006 (3)
C150.055 (3)0.068 (3)0.058 (2)0.004 (2)0.019 (2)0.007 (2)
C160.086 (3)0.084 (3)0.081 (3)0.005 (2)0.034 (2)0.024 (3)
C170.096 (4)0.095 (4)0.086 (3)0.007 (3)0.042 (3)0.012 (3)
C180.086 (4)0.077 (3)0.102 (4)0.002 (3)0.046 (3)0.001 (3)
C190.058 (3)0.065 (4)0.085 (5)0.001 (3)0.031 (3)0.013 (3)
C200.056 (3)0.052 (3)0.050 (2)0.010 (3)0.0118 (18)0.002 (2)
C12'0.057 (3)0.046 (2)0.0506 (19)0.0010 (17)0.0190 (18)0.0007 (19)
C13'0.061 (3)0.055 (3)0.078 (3)0.000 (2)0.028 (2)0.006 (2)
C14'0.064 (3)0.071 (4)0.084 (4)0.003 (3)0.022 (3)0.006 (3)
C15'0.055 (3)0.068 (3)0.058 (2)0.004 (2)0.019 (2)0.007 (2)
C16'0.086 (3)0.084 (3)0.081 (3)0.005 (2)0.034 (2)0.024 (3)
C17'0.096 (4)0.095 (4)0.086 (3)0.007 (3)0.042 (3)0.012 (3)
C18'0.086 (4)0.077 (3)0.102 (4)0.002 (3)0.046 (3)0.001 (3)
C19'0.058 (3)0.065 (4)0.085 (5)0.001 (3)0.031 (3)0.013 (3)
C20'0.056 (3)0.052 (3)0.050 (2)0.010 (3)0.0118 (18)0.002 (2)
Geometric parameters (Å, º) top
O1—C111.215 (4)C14—C151.459 (6)
N1—C111.336 (4)C14—H140.9300
N1—C11.401 (4)C15—C161.3900
N1—H1A0.8600C15—C201.3900
C1—C101.353 (4)C16—C171.3900
C1—C21.385 (4)C16—H16A0.9300
C2—C31.355 (5)C17—C181.3900
C2—H2A0.9300C17—H17A0.9300
C3—C41.407 (5)C18—C191.3900
C3—H3A0.9300C18—H18A0.9300
C4—C91.407 (4)C19—C201.3900
C4—C51.414 (4)C19—H19A0.9300
C5—C61.346 (5)C12'—C20'1.528 (5)
C5—H5A0.9300C12'—C13'1.549 (6)
C6—C71.384 (5)C13'—C14'1.299 (11)
C6—H6A0.9300C13'—H13'0.9300
C7—C81.355 (4)C14'—C15'1.460 (8)
C7—H7A0.9300C14'—H14'0.9300
C8—C91.411 (4)C15'—C16'1.3900
C8—H8A0.9300C15'—C20'1.3900
C9—C101.410 (4)C16'—C17'1.3900
C10—C121.527 (4)C16'—H16B0.9300
C10—C12'1.569 (5)C17'—C18'1.3900
C11—C121.576 (5)C17'—H17B0.9300
C11—C12'1.577 (5)C18'—C19'1.3900
C12—C201.507 (5)C18'—H18B0.9300
C12—C131.530 (5)C19'—C20'1.3900
C13—C141.296 (9)C19'—H19B0.9300
C13—H130.9300
C11—N1—C1111.0 (2)C13—C14—C15109.6 (6)
C11—N1—H1A124.5C13—C14—H14125.2
C1—N1—H1A124.5C15—C14—H14125.2
C10—C1—C2122.6 (3)C16—C15—C20120.0
C10—C1—N1110.4 (3)C16—C15—C14131.5 (4)
C2—C1—N1127.0 (3)C20—C15—C14108.5 (4)
C3—C2—C1117.5 (3)C15—C16—C17120.0
C3—C2—H2A121.2C15—C16—H16A120.0
C1—C2—H2A121.2C17—C16—H16A120.0
C2—C3—C4122.4 (3)C18—C17—C16120.0
C2—C3—H3A118.8C18—C17—H17A120.0
C4—C3—H3A118.8C16—C17—H17A120.0
C9—C4—C3119.5 (3)C17—C18—C19120.0
C9—C4—C5118.2 (3)C17—C18—H18A120.0
C3—C4—C5122.3 (3)C19—C18—H18A120.0
C6—C5—C4121.3 (4)C20—C19—C18120.0
C6—C5—H5A119.3C20—C19—H19A120.0
C4—C5—H5A119.3C18—C19—H19A120.0
C5—C6—C7120.4 (3)C19—C20—C15120.0
C5—C6—H6A119.8C19—C20—C12130.8 (3)
C7—C6—H6A119.8C15—C20—C12109.1 (3)
C8—C7—C6120.5 (3)C20'—C12'—C13'99.5 (4)
C8—C7—H7A119.7C20'—C12'—C10115.4 (4)
C6—C7—H7A119.7C13'—C12'—C10121.4 (4)
C7—C8—C9120.8 (3)C20'—C12'—C11101.0 (4)
C7—C8—H8A119.6C13'—C12'—C11121.9 (5)
C9—C8—H8A119.6C10—C12'—C1196.8 (3)
C10—C9—C4117.1 (3)C14'—C13'—C12'111.1 (7)
C10—C9—C8124.2 (3)C14'—C13'—H13'124.4
C4—C9—C8118.7 (3)C12'—C13'—H13'124.4
C1—C10—C9121.0 (3)C13'—C14'—C15'111.6 (8)
C1—C10—C12107.3 (3)C13'—C14'—H14'124.2
C9—C10—C12129.3 (3)C15'—C14'—H14'124.2
C1—C10—C12'106.0 (3)C16'—C15'—C20'120.0
C9—C10—C12'129.1 (3)C16'—C15'—C14'132.9 (6)
C12—C10—C12'34.7 (2)C20'—C15'—C14'107.0 (6)
O1—C11—N1125.3 (3)C17'—C16'—C15'120.0
O1—C11—C12126.6 (3)C17'—C16'—H16B120.0
N1—C11—C12106.3 (3)C15'—C16'—H16B120.0
O1—C11—C12'124.8 (3)C16'—C17'—C18'120.0
N1—C11—C12'106.2 (3)C16'—C17'—H17B120.0
C12—C11—C12'34.1 (2)C18'—C17'—H17B120.0
C20—C12—C10113.7 (3)C19'—C18'—C17'120.0
C20—C12—C13100.6 (4)C19'—C18'—H18B120.0
C10—C12—C13119.5 (4)C17'—C18'—H18B120.0
C20—C12—C11105.5 (3)C18'—C19'—C20'120.0
C10—C12—C1198.6 (3)C18'—C19'—H19B120.0
C13—C12—C11118.8 (4)C20'—C19'—H19B120.0
C14—C13—C12112.0 (5)C19'—C20'—C15'120.0
C14—C13—H13124.0C19'—C20'—C12'129.3 (4)
C12—C13—H13124.0C15'—C20'—C12'110.6 (4)
C11—N1—C1—C100.2 (4)C14—C15—C16—C17179.7 (5)
C11—N1—C1—C2180.0 (4)C15—C16—C17—C180.0
C10—C1—C2—C30.6 (5)C16—C17—C18—C190.0
N1—C1—C2—C3179.1 (3)C17—C18—C19—C200.0
C1—C2—C3—C40.5 (6)C18—C19—C20—C150.0
C2—C3—C4—C90.1 (6)C18—C19—C20—C12176.9 (4)
C2—C3—C4—C5178.4 (4)C16—C15—C20—C190.0
C9—C4—C5—C60.4 (6)C14—C15—C20—C19179.8 (4)
C3—C4—C5—C6178.7 (4)C16—C15—C20—C12177.5 (4)
C4—C5—C6—C70.0 (6)C14—C15—C20—C122.2 (4)
C5—C6—C7—C80.2 (6)C10—C12—C20—C1951.5 (5)
C6—C7—C8—C90.0 (6)C13—C12—C20—C19179.5 (3)
C3—C4—C9—C100.1 (5)C11—C12—C20—C1955.4 (4)
C5—C4—C9—C10178.2 (3)C10—C12—C20—C15131.3 (3)
C3—C4—C9—C8178.9 (3)C13—C12—C20—C152.3 (4)
C5—C4—C9—C80.6 (5)C11—C12—C20—C15121.8 (3)
C7—C8—C9—C10178.3 (3)C1—C10—C12'—C20'134.1 (4)
C7—C8—C9—C40.4 (5)C9—C10—C12'—C20'68.5 (5)
C2—C1—C10—C90.4 (5)C12—C10—C12'—C20'36.6 (4)
N1—C1—C10—C9179.4 (3)C1—C10—C12'—C13'105.7 (5)
C2—C1—C10—C12163.6 (3)C9—C10—C12'—C13'51.8 (7)
N1—C1—C10—C1216.6 (4)C12—C10—C12'—C13'156.9 (7)
C2—C1—C10—C12'160.1 (3)C1—C10—C12'—C1128.4 (4)
N1—C1—C10—C12'19.7 (4)C9—C10—C12'—C11174.1 (4)
C4—C9—C10—C10.0 (5)C12—C10—C12'—C1169.0 (4)
C8—C9—C10—C1178.7 (3)O1—C11—C12'—C20'54.7 (6)
C4—C9—C10—C12160.1 (3)N1—C11—C12'—C20'146.2 (4)
C8—C9—C10—C1221.1 (6)C12—C11—C12'—C20'50.8 (4)
C4—C9—C10—C12'154.6 (4)O1—C11—C12'—C13'54.0 (8)
C8—C9—C10—C12'24.2 (6)N1—C11—C12'—C13'105.1 (5)
C1—N1—C11—O1178.9 (5)C12—C11—C12'—C13'159.5 (7)
C1—N1—C11—C1215.7 (4)O1—C11—C12'—C10172.2 (5)
C1—N1—C11—C12'19.9 (5)N1—C11—C12'—C1028.6 (4)
C1—C10—C12—C20134.8 (3)C12—C11—C12'—C1066.8 (4)
C9—C10—C12—C2063.0 (5)C20'—C12'—C13'—C14'3.7 (9)
C12'—C10—C12—C2041.5 (4)C10—C12'—C13'—C14'131.5 (8)
C1—C10—C12—C13106.5 (4)C11—C12'—C13'—C14'105.7 (9)
C9—C10—C12—C1355.7 (6)C12'—C13'—C14'—C15'4.1 (12)
C12'—C10—C12—C13160.1 (6)C13'—C14'—C15'—C16'178.9 (6)
C1—C10—C12—C1123.6 (4)C13'—C14'—C15'—C20'2.7 (11)
C9—C10—C12—C11174.2 (4)C20'—C15'—C16'—C17'0.0
C12'—C10—C12—C1169.8 (4)C14'—C15'—C16'—C17'175.8 (8)
O1—C11—C12—C2053.8 (6)C15'—C16'—C17'—C18'0.0
N1—C11—C12—C20141.0 (4)C16'—C17'—C18'—C19'0.0
C12'—C11—C12—C2046.1 (4)C17'—C18'—C19'—C20'0.0
O1—C11—C12—C10171.5 (5)C18'—C19'—C20'—C15'0.0
N1—C11—C12—C1023.4 (4)C18'—C19'—C20'—C12'176.2 (5)
C12'—C11—C12—C1071.5 (4)C16'—C15'—C20'—C19'0.0
O1—C11—C12—C1358.0 (7)C14'—C15'—C20'—C19'176.8 (6)
N1—C11—C12—C13107.2 (5)C16'—C15'—C20'—C12'176.9 (4)
C12'—C11—C12—C13157.9 (6)C14'—C15'—C20'—C12'0.1 (7)
C20—C12—C13—C141.7 (6)C13'—C12'—C20'—C19'178.5 (4)
C10—C12—C13—C14126.8 (5)C10—C12'—C20'—C19'49.9 (6)
C11—C12—C13—C14112.8 (5)C11—C12'—C20'—C19'53.2 (5)
C12—C13—C14—C150.4 (7)C13'—C12'—C20'—C15'2.0 (5)
C13—C14—C15—C16178.6 (4)C10—C12'—C20'—C15'133.6 (4)
C13—C14—C15—C201.2 (6)C11—C12'—C20'—C15'123.3 (4)
C20—C15—C16—C170.0
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O1i0.861.992.815 (3)162
C18—H18A···O1ii0.932.353.064 (5)133
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1, y1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC20H13NO
Mr283.31
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)13.0150 (18), 7.9180 (11), 15.537 (2)
β (°) 112.030 (2)
V3)1484.2 (4)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.50 × 0.41 × 0.33
Data collection
DiffractometerRigaku Mercury
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
6913, 2526, 1984
Rint0.025
(sin θ/λ)max1)0.588
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.074, 0.199, 1.06
No. of reflections2526
No. of parameters203
No. of restraints30
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.23, 0.27

Computer programs: CrystalClear (Rigaku/MSC, 2001), CrystalStructure (Rigaku/MSC, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPII (Johnson, 1976).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O1i0.861.992.815 (3)162
C18—H18A···O1ii0.932.353.064 (5)133
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1, y1/2, z+1/2.
 

Acknowledgements

This work was supported by the Medical Scientific Research Foundation of Guangdong Province (No. B107) and the Guangzhou Municipal Scientific and Technological Project, China (No. 2007 J1-C0251).

References

First citationChen, Z.-P., Tan, D.-M., Su, C.-Y. & Xu, Z.-L. (2005). Acta Cryst. E61, o1308–o1309.  Web of Science CSD CrossRef IUCr Journals
First citationJohnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA.
First citationReady, J. M., Reisman, S. E. & Hirata, M. (2004). Angew. Chem. Int. Ed. 43, 1270–1273.  CAS
First citationRigaku/MSC (2001). CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA.
First citationRigaku/MSC, (2004). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.
First citationSchoemaker, H. E. & Speckamp, W. N. (1978). Tetrahedron Lett. 19, 1515–1518.  CrossRef
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationTsuda, M., Kasai, Y. & Komatsu, K. (2004). Org. Lett. 6, 3087–3089.  Web of Science CrossRef PubMed CAS

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