organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

N-[11-(4-Chloro­phen­yl)-11,12-di­hydro­benzo[c]phenanthridin-6-yl]benzamide

aSchool of Chemistry and Chemical Engineering, Jiangsu University, Zhenjiang, Jiangsu Province 212013, People's Republic of China, bSchool of the Environment, Jiangsu University, Zhenjiang, Jiangsu Province 212013, People's Republic of China, and cSchool of Pharmacy, Jiangsu University, Zhenjiang, Jiangsu Province 212013, People's Republic of China
*Correspondence e-mail: zhangminnk@163.com

(Received 22 October 2010; accepted 25 October 2010; online 31 October 2010)

There are two independent mol­ecules in the asymmetric unit of the title compound, C30H21ClN2O, which differ slightly in the orientation of the unsubstituted phenyl ring. Inter­molecular C—H⋯π inter­actions stabilize the crystal structure. The crystal studied was found to be a racemic twin. The dihedral angles between the substituted phenyl ring and the benzo[c]phenanthridine system are 87.13 (5) and 79.25 (5)° in the two molecules.

Related literature

There are many useful pharmacological properties of benzo[c]phenanthridine derivatives (Clement et al., 2005[Clement, B., Weide, M., Wolschendorf, U. & Kock, I. (2005). Angew. Chem. Int. Ed. 44, 635-638.]). For their anti­tumour activity, see: Stermitz et al. (1973[Stermitz, F. R., Larson, K. A. & Kim, D. K. (1973). J. Med. Chem. 16, 939-940.], 1975[Stermitz, F. R., Gillespie, J. P., Amoros, L. G., Romero, R., Stermitz, T. A., Larson, K. A., Earl, S. & Ogg, J. E. (1975). J. Med. Chem. 18, 708-713.]); Fang et al. (1993[Fang, S. D., Wang, L. K. & Hecht, S. M. (1993). J. Org. Chem. 58, 5025-5027.]); Suzuki et al. (1992[Suzuki, M., Nakanishi, T., Kogawa, O., Ishikawa, K., Kobayashi, F. & Ekimoto, H. (1992). Eur. Patent 487930.]); Kanzawa et al. (1997[Kanzawa, F., Nishio, K., Ishida, T., Fukuda, M., Kurokawa, H., Fukumoto, H., Nomoto, Y., Fukuoka, K., Bojanowski, K. & Saijo, N. (1997). Br. J. Cancer, 76, 571-581.]); Guo et al. (2007[Guo, L., Liu, X. J., Nishikawa, K. & Plunkett, W. (2007). Mol. Cancer Ther. 6, 1501-1508.]); for their anti­microbial activity, see: Nissanka et al. (2001[Nissanka, A. P. K., Karunaratne, V., Bandara, B. M. R., Kumar, V., Nakanishi, T., Nishi, M., Inada, A., Tillekeratne, L. M. V., Wijesundara, D. S. A. & Gunatilaka, A. A. L. (2001). Phytochemistry, 56, 857-861.]); for their anti inflammatory activity, see: Lenfeld et al. (1981[Lenfeld, J., Kroutil, M., Marsalek, E., Slavik, J., Preininger, V. & Simanek, V. (1981). Planta Med. 43, 161-165.]); for their anti­tuberculosis activity, see: Ishikawa (2001[Ishikawa, T. (2001). Med. Res. Rev. 21, 61-72.]). For the synthesis of the starting material, see: Zhang et al. (2008[Zhang, M., Mao, S.-J., Lv, P., Xie, L.-G. & Xu, X.-H. (2008). Chin. J. Org. Chem. 28, 1590-1597.]).

[Scheme 1]

Experimental

Crystal data
  • C30H21ClN2O

  • Mr = 460.94

  • Orthorhombic, P c a 21

  • a = 26.567 (5) Å

  • b = 9.6752 (19) Å

  • c = 17.329 (4) Å

  • V = 4454.5 (15) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.20 mm−1

  • T = 113 K

  • 0.20 × 0.18 × 0.10 mm

Data collection
  • Rigaku Saturn724 CCD diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2009[Rigaku (2009). CrystalClear. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.961, Tmax = 0.980

  • 27069 measured reflections

  • 8288 independent reflections

  • 7795 reflections with I > 2σ(I)

  • Rint = 0.038

Refinement
  • R[F2 > 2σ(F2)] = 0.040

  • wR(F2) = 0.103

  • S = 1.06

  • 8288 reflections

  • 613 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.52 e Å−3

  • Δρmin = −0.47 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), with 3751 Friedel pairs

  • Flack parameter: 0.46 (5)

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the C1–C6, C47–C52 and C17–C22 rings, respectively.

D—H⋯A D—H H⋯A DA D—H⋯A
C26—H26⋯Cg1i 0.93 2.86 3.668 (2) 146
C28—H28⋯Cg2ii 0.93 2.76 3.610 (3) 152
C58—H58⋯Cg3iii 0.93 2.84 3.588 (3) 138
Symmetry codes: (i) [-x+{\script{1\over 2}}, y, z-{\script{1\over 2}}]; (ii) [-x, -y+1, z-{\script{1\over 2}}]; (iii) [-x+{\script{1\over 2}}, y, z+{\script{1\over 2}}].

Data collection: CrystalClear (Rigaku, 2009[Rigaku (2009). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

Benzo[c]phenanthridine derivatives are a class of substances possesing a wide range of pharmacological properties. Many naturally occurring alkaloids that contain a benzo[c]phenanthridine ring system and demonstrate interesting biological activities are mentioned in the literature (Clement et al., 2005). For example, antitumor activity (Stermitz et al., 1973, 1975; Fang et al., 1993; Suzuki et al., 1992; Kanzawa et al., 1997; Guo et al., 2007), antimicrobial activity (Nissanka et al., 2001), anti-inflammatory activity (Lenfeld et al., 1981) and antituberculosis activity (Ishikawa, 2001). Because of a strong interest in the biological activities associated with benzo[c]phenanthridine compounds, the title compound, (I), was synthesized and its structure is reported here.

The asymmetric unit of (I) contains two independent molecules (Fig. 1). The dihedral angle between the phenyl ring C1–C6 and the benzo[c]phenanthridine ring C7–C23/N1 is 87.13 (5)°, and that between the phenyl ring C31–C36 and the benzo[c]phenanthridine ring C37–C53/N3 is 79.25 (5)°. The C23—N2—C24—C25 and C53—N4—C54—C55 torision angles are 171.15 (19)° and -171.66 (18)°, respectively. And the intermolecular C—H···π interactions stablize the crystal structure (Fig. 2).

Related literature top

There are many useful pharmacological properties of benzo[c]phenanthridine derivatives (Clement et al., 2005). For their antitumour activity, see: Stermitz et al. (1973, 1975); Fang et al. (1993); Suzuki et al. (1992); Kanzawa et al. (1997); Guo et al. (2007); for their antimicrobial activity, see: Nissanka et al. (2001); for their anti inflammatory activity, see: Lenfeld et al. (1981); for their antituberculosis activity, see: Ishikawa (2001). For the synthesis of the starting material, see: Zhang et al. (2008). [Note two references added - please check added text]

Experimental top

To 15 ml dry dichloromethane, 11-(4-chlorophenyl)-6-amino-11,12-2H-benzo[c]phenanthridine (0.36 g, 1.0 mmol, prepared according to the reported procedure (Zhang et al., 2008)) and triethylamine (0.18 ml, 1.3 mmol) were added. The mixture was stirred for 30 min at room temperature. A solution of benzoyl chloride (0.17 g, 1.2 mmol) in 3 ml of dry dichloromethane was added dropwise to the above mixture with stirring at room temperature. After completion of the reaction (monitored on TLC), the solvent was removed under vacuum, and the residue was dissolved in 30 ml of water and extracted with dichloromethane. The combined organic phase was dried over sodium sulfate and concentrated under reduced pressure. The resulting crude product was recrystallized from petroleum ether and ethyl acetate. Single crystals of (I) suitable for X-ray diffraction were obtained after slow evaporation of the mother liquor.

Refinement top

All H atoms were placed in calculated positions, with C—H = 0.93, 0.97 or 0.98 Å and N—H = 0.86 Å, and included in the final cycles of refinement using a riding model, with Uiso(H) = 1.2Ueq(C).

Structure description top

Benzo[c]phenanthridine derivatives are a class of substances possesing a wide range of pharmacological properties. Many naturally occurring alkaloids that contain a benzo[c]phenanthridine ring system and demonstrate interesting biological activities are mentioned in the literature (Clement et al., 2005). For example, antitumor activity (Stermitz et al., 1973, 1975; Fang et al., 1993; Suzuki et al., 1992; Kanzawa et al., 1997; Guo et al., 2007), antimicrobial activity (Nissanka et al., 2001), anti-inflammatory activity (Lenfeld et al., 1981) and antituberculosis activity (Ishikawa, 2001). Because of a strong interest in the biological activities associated with benzo[c]phenanthridine compounds, the title compound, (I), was synthesized and its structure is reported here.

The asymmetric unit of (I) contains two independent molecules (Fig. 1). The dihedral angle between the phenyl ring C1–C6 and the benzo[c]phenanthridine ring C7–C23/N1 is 87.13 (5)°, and that between the phenyl ring C31–C36 and the benzo[c]phenanthridine ring C37–C53/N3 is 79.25 (5)°. The C23—N2—C24—C25 and C53—N4—C54—C55 torision angles are 171.15 (19)° and -171.66 (18)°, respectively. And the intermolecular C—H···π interactions stablize the crystal structure (Fig. 2).

There are many useful pharmacological properties of benzo[c]phenanthridine derivatives (Clement et al., 2005). For their antitumour activity, see: Stermitz et al. (1973, 1975); Fang et al. (1993); Suzuki et al. (1992); Kanzawa et al. (1997); Guo et al. (2007); for their antimicrobial activity, see: Nissanka et al. (2001); for their anti inflammatory activity, see: Lenfeld et al. (1981); for their antituberculosis activity, see: Ishikawa (2001). For the synthesis of the starting material, see: Zhang et al. (2008). [Note two references added - please check added text]

Computing details top

Data collection: CrystalClear (Rigaku, 2009); cell refinement: CrystalClear (Rigaku, 2009); data reduction: CrystalClear (Rigaku, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of the title compound, (I), with displacement ellipsoids drawn at the 30% probability level.
[Figure 2] Fig. 2. The packing diagram of the title compound. Intermolecular C—H···π interactions are shown as dashed line.
N-[11-(4-Chlorophenyl)-11,12- dihydrobenzo[c]phenanthridin-6-yl]benzamide top
Crystal data top
C30H21ClN2OF(000) = 1920
Mr = 460.94Dx = 1.375 Mg m3
Orthorhombic, Pca21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2acCell parameters from 10393 reflections
a = 26.567 (5) Åθ = 1.5–26.1°
b = 9.6752 (19) ŵ = 0.20 mm1
c = 17.329 (4) ÅT = 113 K
V = 4454.5 (15) Å3Block, yellow
Z = 80.20 × 0.18 × 0.10 mm
Data collection top
Rigaku Saturn724 CCD
diffractometer
8288 independent reflections
Radiation source: rotating anode7795 reflections with I > 2σ(I)
Confocal monochromatorRint = 0.038
ω scansθmax = 26.1°, θmin = 2.1°
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2009)
h = 2832
Tmin = 0.961, Tmax = 0.980k = 1111
27069 measured reflectionsl = 2120
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040H-atom parameters constrained
wR(F2) = 0.103 w = 1/[σ2(Fo2) + (0.0607P)2 + 0.6857P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.001
8288 reflectionsΔρmax = 0.52 e Å3
613 parametersΔρmin = 0.47 e Å3
1 restraintAbsolute structure: Flack (1983), with how many Friedel pairs?
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.46 (5)
Crystal data top
C30H21ClN2OV = 4454.5 (15) Å3
Mr = 460.94Z = 8
Orthorhombic, Pca21Mo Kα radiation
a = 26.567 (5) ŵ = 0.20 mm1
b = 9.6752 (19) ÅT = 113 K
c = 17.329 (4) Å0.20 × 0.18 × 0.10 mm
Data collection top
Rigaku Saturn724 CCD
diffractometer
8288 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2009)
7795 reflections with I > 2σ(I)
Tmin = 0.961, Tmax = 0.980Rint = 0.038
27069 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.040H-atom parameters constrained
wR(F2) = 0.103Δρmax = 0.52 e Å3
S = 1.06Δρmin = 0.47 e Å3
8288 reflectionsAbsolute structure: Flack (1983), with how many Friedel pairs?
613 parametersAbsolute structure parameter: 0.46 (5)
1 restraint
Special details top

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*/Ueq
Cl10.45020 (2)1.04494 (6)0.45992 (4)0.03290 (15)
Cl20.18314 (2)0.43588 (7)0.22904 (4)0.03730 (16)
O10.15812 (6)0.44686 (15)0.20860 (9)0.0228 (4)
O20.09263 (6)1.12523 (16)0.48412 (10)0.0252 (4)
N10.19235 (6)0.62652 (18)0.30450 (11)0.0184 (4)
N20.14648 (6)0.68325 (18)0.19207 (11)0.0189 (4)
H20.13510.74610.16160.023*
N30.06092 (6)0.94686 (19)0.38501 (11)0.0172 (4)
N40.10706 (6)0.88891 (19)0.49698 (11)0.0184 (4)
H40.11960.82570.52610.022*
C10.29080 (7)0.8823 (2)0.47123 (13)0.0178 (4)
C20.30981 (8)0.9683 (2)0.52866 (14)0.0220 (5)
H2A0.28940.99220.57010.026*
C30.35835 (8)1.0189 (2)0.52532 (14)0.0224 (5)
H30.37071.07530.56440.027*
C40.38840 (7)0.9845 (2)0.46298 (15)0.0211 (5)
C50.37101 (9)0.8999 (2)0.40441 (14)0.0242 (5)
H50.39150.87740.36280.029*
C60.32217 (8)0.8495 (2)0.40923 (13)0.0214 (5)
H60.31010.79250.37020.026*
C70.23727 (7)0.8285 (2)0.47799 (13)0.0195 (5)
H70.21700.90320.50010.023*
C80.23284 (8)0.7046 (2)0.53287 (14)0.0237 (5)
H8A0.25370.72130.57780.028*
H8B0.19830.69720.55030.028*
C90.24816 (8)0.5706 (2)0.49689 (14)0.0234 (5)
C100.27108 (9)0.4670 (3)0.53995 (16)0.0304 (6)
H100.27700.48090.59230.036*
C110.28521 (9)0.3431 (3)0.50603 (17)0.0349 (6)
H110.30120.27550.53530.042*
C120.27543 (9)0.3201 (3)0.42832 (17)0.0314 (6)
H120.28480.23700.40540.038*
C130.25159 (9)0.4216 (2)0.38485 (15)0.0254 (5)
H130.24470.40580.33300.030*
C140.23787 (8)0.5470 (2)0.41858 (15)0.0214 (5)
C150.21420 (8)0.6601 (2)0.37485 (13)0.0188 (5)
C160.21424 (7)0.7929 (2)0.40035 (13)0.0187 (4)
C170.19362 (7)0.8995 (2)0.35147 (13)0.0178 (5)
C180.19268 (8)1.0404 (2)0.37309 (14)0.0202 (5)
H180.20641.06720.42020.024*
C190.17182 (8)1.1380 (2)0.32543 (14)0.0225 (5)
H190.17151.23010.34090.027*
C200.15087 (8)1.1017 (2)0.25353 (14)0.0233 (5)
H200.13731.16910.22140.028*
C210.15077 (8)0.9652 (2)0.23163 (14)0.0208 (5)
H210.13650.93990.18470.025*
C220.17193 (7)0.8637 (2)0.27943 (13)0.0173 (4)
C230.17036 (7)0.7198 (2)0.25644 (12)0.0170 (4)
C240.13982 (8)0.5481 (2)0.17403 (13)0.0195 (5)
C250.10550 (8)0.5262 (2)0.10631 (13)0.0205 (5)
C260.09983 (9)0.6261 (2)0.04939 (14)0.0236 (5)
H260.11830.70760.05200.028*
C270.06682 (10)0.6050 (3)0.01121 (15)0.0313 (6)
H270.06370.67150.04970.038*
C280.03835 (9)0.4848 (3)0.01481 (15)0.0302 (6)
H280.01580.47150.05520.036*
C290.04355 (10)0.3858 (3)0.04136 (16)0.0316 (6)
H290.02420.30580.03920.038*
C300.07772 (9)0.4044 (2)0.10169 (15)0.0265 (5)
H300.08190.33580.13870.032*
C310.03808 (7)0.6800 (2)0.21873 (13)0.0186 (4)
C320.06480 (8)0.6718 (2)0.28733 (14)0.0245 (5)
H320.05240.71600.33110.029*
C330.11012 (9)0.5983 (3)0.29190 (15)0.0275 (5)
H330.12760.59150.33830.033*
C340.12821 (8)0.5360 (2)0.22564 (15)0.0241 (5)
C350.10328 (9)0.5472 (2)0.15631 (15)0.0272 (5)
H350.11670.50730.11210.033*
C360.05835 (8)0.6178 (2)0.15263 (14)0.0237 (5)
H360.04130.62430.10590.028*
C370.01430 (7)0.7465 (2)0.21222 (13)0.0191 (5)
H370.03610.67590.18930.023*
C380.01665 (8)0.8709 (2)0.15749 (14)0.0228 (5)
H38A0.05080.88050.13830.027*
H38B0.00510.85350.11360.027*
C390.00102 (8)1.0040 (2)0.19526 (14)0.0220 (5)
C400.02315 (8)1.1084 (2)0.15437 (15)0.0271 (5)
H400.03091.09470.10260.032*
C410.03583 (9)1.2323 (3)0.18932 (17)0.0320 (6)
H410.05211.30070.16100.038*
C420.02439 (9)1.2545 (3)0.26580 (16)0.0293 (6)
H420.03311.33760.28930.035*
C430.00040 (8)1.1519 (2)0.30821 (15)0.0226 (5)
H430.00821.16680.35990.027*
C440.01337 (8)1.0272 (2)0.27295 (14)0.0193 (5)
C450.03790 (7)0.9143 (2)0.31547 (13)0.0176 (4)
C460.03744 (7)0.7808 (2)0.28962 (12)0.0169 (4)
C470.05878 (7)0.6743 (2)0.33760 (13)0.0177 (4)
C480.05844 (8)0.5332 (2)0.31640 (14)0.0191 (4)
H480.04410.50660.26980.023*
C490.07913 (8)0.4348 (2)0.36405 (14)0.0223 (5)
H490.07920.34280.34850.027*
C500.10022 (8)0.4701 (2)0.43567 (15)0.0243 (5)
H500.11350.40230.46780.029*
C510.10092 (8)0.6073 (2)0.45760 (15)0.0224 (5)
H510.11510.63200.50470.027*
C520.08047 (7)0.7101 (2)0.40953 (13)0.0167 (4)
C530.08287 (7)0.8534 (2)0.43261 (13)0.0177 (4)
C540.11219 (8)1.0245 (2)0.51734 (14)0.0199 (5)
C550.14664 (8)1.0465 (2)0.58493 (13)0.0205 (5)
C560.17109 (8)1.1721 (2)0.59367 (15)0.0270 (5)
H560.16561.24270.55830.032*
C570.20390 (9)1.1930 (3)0.65529 (17)0.0330 (6)
H570.22031.27740.66090.040*
C580.21214 (9)1.0887 (3)0.70806 (15)0.0329 (6)
H580.23391.10300.74930.039*
C590.18785 (9)0.9620 (3)0.69954 (16)0.0315 (6)
H590.19340.89140.73500.038*
C600.15552 (8)0.9418 (2)0.63837 (14)0.0248 (5)
H600.13940.85710.63270.030*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0214 (3)0.0420 (3)0.0352 (3)0.0113 (2)0.0024 (2)0.0036 (3)
Cl20.0298 (3)0.0409 (3)0.0412 (4)0.0124 (3)0.0001 (3)0.0072 (3)
O10.0246 (8)0.0233 (8)0.0205 (9)0.0035 (6)0.0023 (6)0.0008 (7)
O20.0262 (8)0.0221 (8)0.0273 (10)0.0040 (7)0.0061 (7)0.0017 (7)
N10.0178 (9)0.0214 (9)0.0159 (10)0.0002 (7)0.0010 (7)0.0020 (8)
N20.0204 (9)0.0182 (9)0.0181 (10)0.0006 (7)0.0014 (7)0.0033 (8)
N30.0133 (8)0.0200 (9)0.0182 (10)0.0004 (7)0.0010 (7)0.0020 (7)
N40.0175 (9)0.0212 (9)0.0164 (10)0.0017 (7)0.0013 (7)0.0014 (8)
C10.0170 (10)0.0178 (10)0.0185 (12)0.0009 (8)0.0018 (8)0.0021 (9)
C20.0232 (11)0.0242 (12)0.0188 (12)0.0023 (9)0.0016 (9)0.0000 (9)
C30.0252 (11)0.0206 (11)0.0216 (12)0.0029 (9)0.0062 (9)0.0013 (9)
C40.0146 (10)0.0225 (11)0.0262 (12)0.0044 (8)0.0030 (9)0.0027 (10)
C50.0230 (11)0.0294 (12)0.0203 (12)0.0001 (10)0.0043 (9)0.0017 (10)
C60.0187 (11)0.0277 (12)0.0179 (12)0.0023 (9)0.0014 (8)0.0034 (10)
C70.0166 (10)0.0252 (11)0.0166 (12)0.0004 (8)0.0025 (8)0.0003 (9)
C80.0192 (11)0.0334 (12)0.0185 (12)0.0058 (9)0.0029 (8)0.0053 (10)
C90.0168 (10)0.0267 (11)0.0268 (14)0.0075 (9)0.0048 (9)0.0079 (10)
C100.0277 (12)0.0330 (14)0.0304 (15)0.0097 (11)0.0121 (10)0.0123 (11)
C110.0298 (13)0.0287 (13)0.0462 (18)0.0045 (11)0.0154 (11)0.0164 (12)
C120.0237 (12)0.0239 (12)0.0464 (17)0.0008 (10)0.0070 (11)0.0064 (12)
C130.0219 (11)0.0246 (11)0.0296 (14)0.0028 (10)0.0056 (9)0.0034 (10)
C140.0134 (10)0.0238 (12)0.0271 (13)0.0019 (8)0.0027 (8)0.0079 (10)
C150.0141 (10)0.0231 (11)0.0190 (12)0.0017 (8)0.0006 (8)0.0035 (9)
C160.0121 (9)0.0276 (12)0.0164 (11)0.0010 (8)0.0003 (8)0.0015 (9)
C170.0111 (10)0.0211 (11)0.0213 (12)0.0013 (8)0.0011 (8)0.0023 (9)
C180.0147 (10)0.0247 (11)0.0211 (12)0.0026 (9)0.0000 (8)0.0033 (9)
C190.0192 (10)0.0205 (11)0.0278 (13)0.0011 (9)0.0020 (9)0.0015 (10)
C200.0215 (11)0.0232 (11)0.0250 (13)0.0023 (9)0.0015 (9)0.0072 (10)
C210.0183 (10)0.0249 (11)0.0193 (12)0.0032 (8)0.0029 (9)0.0016 (10)
C220.0139 (9)0.0225 (11)0.0154 (11)0.0016 (8)0.0004 (8)0.0003 (9)
C230.0147 (10)0.0205 (11)0.0158 (11)0.0009 (8)0.0025 (8)0.0037 (9)
C240.0159 (10)0.0234 (11)0.0191 (12)0.0016 (9)0.0039 (8)0.0012 (9)
C250.0174 (10)0.0266 (12)0.0175 (12)0.0021 (9)0.0012 (8)0.0052 (9)
C260.0275 (12)0.0222 (11)0.0212 (13)0.0062 (9)0.0015 (9)0.0011 (10)
C270.0363 (14)0.0365 (14)0.0212 (13)0.0051 (11)0.0066 (10)0.0045 (11)
C280.0283 (12)0.0366 (14)0.0256 (14)0.0045 (11)0.0071 (9)0.0063 (11)
C290.0342 (13)0.0285 (13)0.0323 (15)0.0092 (11)0.0042 (10)0.0057 (11)
C300.0315 (13)0.0239 (12)0.0241 (13)0.0022 (10)0.0023 (10)0.0001 (10)
C310.0187 (10)0.0164 (10)0.0207 (12)0.0038 (8)0.0025 (8)0.0007 (9)
C320.0240 (11)0.0294 (12)0.0202 (13)0.0020 (10)0.0008 (9)0.0061 (10)
C330.0229 (12)0.0335 (13)0.0261 (14)0.0010 (10)0.0030 (9)0.0019 (11)
C340.0183 (10)0.0248 (12)0.0292 (13)0.0010 (9)0.0028 (10)0.0018 (11)
C350.0260 (12)0.0283 (12)0.0275 (14)0.0016 (10)0.0072 (10)0.0068 (10)
C360.0284 (12)0.0250 (12)0.0177 (12)0.0004 (9)0.0001 (9)0.0028 (10)
C370.0170 (10)0.0228 (11)0.0174 (12)0.0028 (8)0.0001 (8)0.0019 (9)
C380.0225 (11)0.0275 (12)0.0182 (12)0.0035 (9)0.0031 (9)0.0030 (10)
C390.0175 (10)0.0253 (11)0.0233 (12)0.0061 (9)0.0045 (9)0.0037 (10)
C400.0247 (12)0.0314 (13)0.0251 (13)0.0031 (10)0.0074 (9)0.0066 (11)
C410.0250 (12)0.0249 (12)0.0462 (17)0.0007 (10)0.0130 (11)0.0132 (12)
C420.0242 (12)0.0208 (12)0.0430 (16)0.0013 (10)0.0045 (11)0.0054 (11)
C430.0172 (10)0.0223 (11)0.0283 (13)0.0021 (9)0.0029 (9)0.0023 (10)
C440.0151 (10)0.0199 (11)0.0228 (13)0.0006 (8)0.0028 (8)0.0041 (9)
C450.0116 (9)0.0220 (10)0.0193 (12)0.0002 (8)0.0001 (8)0.0002 (9)
C460.0141 (10)0.0217 (11)0.0150 (11)0.0002 (8)0.0011 (8)0.0022 (9)
C470.0112 (10)0.0225 (11)0.0193 (12)0.0008 (8)0.0042 (8)0.0028 (9)
C480.0180 (10)0.0207 (11)0.0185 (12)0.0024 (8)0.0009 (8)0.0024 (9)
C490.0207 (11)0.0182 (11)0.0280 (14)0.0015 (9)0.0012 (9)0.0013 (10)
C500.0212 (11)0.0232 (12)0.0285 (14)0.0015 (9)0.0033 (9)0.0073 (10)
C510.0203 (10)0.0266 (11)0.0202 (12)0.0029 (9)0.0022 (9)0.0028 (10)
C520.0134 (9)0.0182 (10)0.0186 (11)0.0020 (8)0.0017 (8)0.0011 (9)
C530.0120 (9)0.0250 (11)0.0160 (11)0.0002 (8)0.0018 (8)0.0035 (9)
C540.0172 (10)0.0235 (12)0.0190 (12)0.0013 (9)0.0017 (8)0.0004 (9)
C550.0157 (10)0.0249 (12)0.0208 (13)0.0010 (9)0.0006 (8)0.0048 (9)
C560.0253 (12)0.0260 (12)0.0297 (14)0.0034 (9)0.0049 (10)0.0023 (11)
C570.0324 (13)0.0307 (13)0.0361 (16)0.0045 (11)0.0086 (11)0.0088 (12)
C580.0282 (13)0.0454 (15)0.0251 (14)0.0004 (11)0.0089 (10)0.0062 (12)
C590.0319 (13)0.0418 (15)0.0209 (13)0.0014 (11)0.0030 (10)0.0065 (11)
C600.0237 (11)0.0298 (12)0.0208 (13)0.0041 (9)0.0008 (9)0.0001 (11)
Geometric parameters (Å, º) top
Cl1—C41.744 (2)C27—C281.388 (4)
Cl2—C341.752 (2)C27—H270.9300
O1—C241.247 (3)C28—C291.373 (4)
O2—C541.245 (3)C28—H280.9300
N1—C231.360 (3)C29—C301.396 (4)
N1—C151.389 (3)C29—H290.9300
N2—C231.331 (3)C30—H300.9300
N2—C241.356 (3)C31—C321.387 (3)
N2—H20.8600C31—C361.401 (3)
N3—C531.356 (3)C31—C371.537 (3)
N3—C451.388 (3)C32—C331.401 (3)
N4—C531.332 (3)C32—H320.9300
N4—C541.366 (3)C33—C341.383 (4)
N4—H40.8600C33—H330.9300
C1—C21.392 (3)C34—C351.376 (4)
C1—C61.396 (3)C35—C361.377 (3)
C1—C71.519 (3)C35—H350.9300
C2—C31.380 (3)C36—H360.9300
C2—H2A0.9300C37—C461.512 (3)
C3—C41.384 (3)C37—C381.533 (3)
C3—H30.9300C37—H370.9800
C4—C51.383 (3)C38—C391.503 (3)
C5—C61.389 (3)C38—H38A0.9700
C5—H50.9300C38—H38B0.9700
C6—H60.9300C39—C401.390 (3)
C7—C161.517 (3)C39—C441.404 (3)
C7—C81.534 (3)C40—C411.385 (4)
C7—H70.9800C40—H400.9300
C8—C91.495 (3)C41—C421.377 (4)
C8—H8A0.9700C41—H410.9300
C8—H8B0.9700C42—C431.400 (3)
C9—C101.390 (3)C42—H420.9300
C9—C141.403 (3)C43—C441.395 (3)
C10—C111.387 (4)C43—H430.9300
C10—H100.9300C44—C451.470 (3)
C11—C121.389 (4)C45—C461.367 (3)
C11—H110.9300C46—C471.440 (3)
C12—C131.391 (3)C47—C481.414 (3)
C12—H120.9300C47—C521.416 (3)
C13—C141.395 (3)C48—C491.375 (3)
C13—H130.9300C48—H480.9300
C14—C151.472 (3)C49—C501.404 (3)
C15—C161.359 (3)C49—H490.9300
C16—C171.443 (3)C50—C511.381 (3)
C17—C181.414 (3)C50—H500.9300
C17—C221.418 (3)C51—C521.407 (3)
C18—C191.372 (3)C51—H510.9300
C18—H180.9300C52—C531.444 (3)
C19—C201.409 (3)C54—C551.502 (3)
C19—H190.9300C55—C561.386 (3)
C20—C211.374 (3)C55—C601.393 (3)
C20—H200.9300C56—C571.393 (3)
C21—C221.402 (3)C56—H560.9300
C21—H210.9300C57—C581.379 (4)
C22—C231.449 (3)C57—H570.9300
C24—C251.501 (3)C58—C591.393 (4)
C25—C261.389 (3)C58—H580.9300
C25—C301.392 (3)C59—C601.379 (3)
C26—C271.383 (3)C59—H590.9300
C26—H260.9300C60—H600.9300
C23—N1—C15124.20 (18)C30—C29—H29119.8
C23—N2—C24120.75 (19)C25—C30—C29119.8 (2)
C23—N2—H2119.6C25—C30—H30120.1
C24—N2—H2119.6C29—C30—H30120.1
C53—N3—C45124.49 (19)C32—C31—C36118.6 (2)
C53—N4—C54120.82 (19)C32—C31—C37123.4 (2)
C53—N4—H4119.6C36—C31—C37117.9 (2)
C54—N4—H4119.6C31—C32—C33121.2 (2)
C2—C1—C6117.99 (19)C31—C32—H32119.4
C2—C1—C7119.32 (19)C33—C32—H32119.4
C6—C1—C7122.69 (19)C34—C33—C32118.2 (2)
C3—C2—C1121.4 (2)C34—C33—H33120.9
C3—C2—H2A119.3C32—C33—H33120.9
C1—C2—H2A119.3C35—C34—C33121.5 (2)
C2—C3—C4119.1 (2)C35—C34—Cl2118.28 (18)
C2—C3—H3120.4C33—C34—Cl2120.16 (19)
C4—C3—H3120.4C34—C35—C36119.8 (2)
C5—C4—C3121.49 (19)C34—C35—H35120.1
C5—C4—Cl1119.38 (18)C36—C35—H35120.1
C3—C4—Cl1119.10 (18)C35—C36—C31120.6 (2)
C4—C5—C6118.4 (2)C35—C36—H36119.7
C4—C5—H5120.8C31—C36—H36119.7
C6—C5—H5120.8C46—C37—C38111.10 (18)
C5—C6—C1121.6 (2)C46—C37—C31113.25 (18)
C5—C6—H6119.2C38—C37—C31114.26 (17)
C1—C6—H6119.2C46—C37—H37105.8
C16—C7—C1112.76 (18)C38—C37—H37105.8
C16—C7—C8109.98 (18)C31—C37—H37105.8
C1—C7—C8112.78 (17)C39—C38—C37113.1 (2)
C16—C7—H7107.0C39—C38—H38A109.0
C1—C7—H7107.0C37—C38—H38A109.0
C8—C7—H7107.0C39—C38—H38B109.0
C9—C8—C7113.4 (2)C37—C38—H38B109.0
C9—C8—H8A108.9H38A—C38—H38B107.8
C7—C8—H8A108.9C40—C39—C44118.7 (2)
C9—C8—H8B108.9C40—C39—C38121.9 (2)
C7—C8—H8B108.9C44—C39—C38119.3 (2)
H8A—C8—H8B107.7C41—C40—C39121.2 (2)
C10—C9—C14119.2 (2)C41—C40—H40119.4
C10—C9—C8121.4 (2)C39—C40—H40119.4
C14—C9—C8119.4 (2)C42—C41—C40120.1 (2)
C11—C10—C9121.0 (3)C42—C41—H41119.9
C11—C10—H10119.5C40—C41—H41119.9
C9—C10—H10119.5C41—C42—C43119.9 (2)
C10—C11—C12119.9 (2)C41—C42—H42120.0
C10—C11—H11120.0C43—C42—H42120.0
C12—C11—H11120.0C44—C43—C42120.0 (2)
C11—C12—C13119.8 (2)C44—C43—H43120.0
C11—C12—H12120.1C42—C43—H43120.0
C13—C12—H12120.1C43—C44—C39120.0 (2)
C12—C13—C14120.4 (2)C43—C44—C45122.2 (2)
C12—C13—H13119.8C39—C44—C45117.7 (2)
C14—C13—H13119.8C46—C45—N3120.2 (2)
C13—C14—C9119.7 (2)C46—C45—C44122.3 (2)
C13—C14—C15122.8 (2)N3—C45—C44117.49 (19)
C9—C14—C15117.4 (2)C45—C46—C47118.9 (2)
C16—C15—N1120.47 (19)C45—C46—C37120.10 (19)
C16—C15—C14122.3 (2)C47—C46—C37121.01 (19)
N1—C15—C14117.17 (19)C48—C47—C52117.9 (2)
C15—C16—C17119.0 (2)C48—C47—C46122.6 (2)
C15—C16—C7120.2 (2)C52—C47—C46119.6 (2)
C17—C16—C7120.8 (2)C49—C48—C47120.7 (2)
C18—C17—C22117.5 (2)C49—C48—H48119.7
C18—C17—C16122.7 (2)C47—C48—H48119.7
C22—C17—C16119.75 (19)C48—C49—C50121.5 (2)
C19—C18—C17120.8 (2)C48—C49—H49119.3
C19—C18—H18119.6C50—C49—H49119.3
C17—C18—H18119.6C51—C50—C49118.9 (2)
C18—C19—C20121.3 (2)C51—C50—H50120.6
C18—C19—H19119.3C49—C50—H50120.6
C20—C19—H19119.3C50—C51—C52120.8 (2)
C21—C20—C19119.0 (2)C50—C51—H51119.6
C21—C20—H20120.5C52—C51—H51119.6
C19—C20—H20120.5C51—C52—C47120.4 (2)
C20—C21—C22120.6 (2)C51—C52—C53119.8 (2)
C20—C21—H21119.7C47—C52—C53119.77 (19)
C22—C21—H21119.7N4—C53—N3123.0 (2)
C21—C22—C17120.8 (2)N4—C53—C52120.06 (19)
C21—C22—C23119.9 (2)N3—C53—C52116.92 (19)
C17—C22—C23119.27 (19)O2—C54—N4126.2 (2)
N2—C23—N1122.8 (2)O2—C54—C55120.3 (2)
N2—C23—C22119.95 (19)N4—C54—C55113.47 (19)
N1—C23—C22117.17 (19)C56—C55—C60119.1 (2)
O1—C24—N2126.6 (2)C56—C55—C54119.7 (2)
O1—C24—C25120.09 (19)C60—C55—C54121.3 (2)
N2—C24—C25113.32 (19)C55—C56—C57120.3 (2)
C26—C25—C30119.4 (2)C55—C56—H56119.9
C26—C25—C24121.5 (2)C57—C56—H56119.9
C30—C25—C24119.1 (2)C58—C57—C56120.1 (2)
C27—C26—C25120.3 (2)C58—C57—H57120.0
C27—C26—H26119.8C56—C57—H57120.0
C25—C26—H26119.8C57—C58—C59120.0 (2)
C26—C27—C28120.2 (2)C57—C58—H58120.0
C26—C27—H27119.9C59—C58—H58120.0
C28—C27—H27119.9C60—C59—C58119.7 (2)
C29—C28—C27119.8 (2)C60—C59—H59120.2
C29—C28—H28120.1C58—C59—H59120.2
C27—C28—H28120.1C59—C60—C55120.9 (2)
C28—C29—C30120.4 (2)C59—C60—H60119.5
C28—C29—H29119.8C55—C60—H60119.5
C6—C1—C2—C30.7 (3)C36—C31—C32—C332.7 (3)
C7—C1—C2—C3179.5 (2)C37—C31—C32—C33173.6 (2)
C1—C2—C3—C40.8 (3)C31—C32—C33—C341.3 (4)
C2—C3—C4—C50.5 (3)C32—C33—C34—C351.2 (4)
C2—C3—C4—Cl1178.46 (18)C32—C33—C34—Cl2176.98 (18)
C3—C4—C5—C60.1 (4)C33—C34—C35—C362.3 (4)
Cl1—C4—C5—C6178.02 (18)Cl2—C34—C35—C36175.94 (18)
C4—C5—C6—C10.1 (3)C34—C35—C36—C310.8 (3)
C2—C1—C6—C50.3 (3)C32—C31—C36—C351.6 (3)
C7—C1—C6—C5179.9 (2)C37—C31—C36—C35174.9 (2)
C2—C1—C7—C16154.6 (2)C32—C31—C37—C469.5 (3)
C6—C1—C7—C1625.2 (3)C36—C31—C37—C46166.81 (19)
C2—C1—C7—C880.1 (3)C32—C31—C37—C38119.0 (2)
C6—C1—C7—C8100.1 (2)C36—C31—C37—C3864.6 (3)
C16—C7—C8—C946.6 (2)C46—C37—C38—C3945.4 (2)
C1—C7—C8—C980.2 (2)C31—C37—C38—C3984.2 (2)
C7—C8—C9—C10146.8 (2)C37—C38—C39—C40147.5 (2)
C7—C8—C9—C1435.2 (3)C37—C38—C39—C4435.8 (3)
C14—C9—C10—C112.0 (3)C44—C39—C40—C411.2 (3)
C8—C9—C10—C11179.9 (2)C38—C39—C40—C41177.8 (2)
C9—C10—C11—C121.5 (4)C39—C40—C41—C420.3 (4)
C10—C11—C12—C130.1 (4)C40—C41—C42—C430.4 (4)
C11—C12—C13—C140.6 (4)C41—C42—C43—C440.1 (3)
C12—C13—C14—C90.1 (3)C42—C43—C44—C390.8 (3)
C12—C13—C14—C15177.8 (2)C42—C43—C44—C45177.9 (2)
C10—C9—C14—C131.2 (3)C40—C39—C44—C431.4 (3)
C8—C9—C14—C13179.3 (2)C38—C39—C44—C43178.2 (2)
C10—C9—C14—C15179.2 (2)C40—C39—C44—C45178.7 (2)
C8—C9—C14—C152.7 (3)C38—C39—C44—C454.6 (3)
C23—N1—C15—C160.6 (3)C53—N3—C45—C461.8 (3)
C23—N1—C15—C14178.02 (19)C53—N3—C45—C44176.6 (2)
C13—C14—C15—C16160.3 (2)C43—C44—C45—C46160.3 (2)
C9—C14—C15—C1617.6 (3)C39—C44—C45—C4616.9 (3)
C13—C14—C15—N118.3 (3)C43—C44—C45—N318.1 (3)
C9—C14—C15—N1163.79 (19)C39—C44—C45—N3164.72 (19)
N1—C15—C16—C173.2 (3)N3—C45—C46—C473.3 (3)
C14—C15—C16—C17175.35 (19)C44—C45—C46—C47175.03 (19)
N1—C15—C16—C7178.80 (18)N3—C45—C46—C37177.39 (18)
C14—C15—C16—C72.6 (3)C44—C45—C46—C374.3 (3)
C1—C7—C16—C1597.6 (2)C38—C37—C46—C4527.0 (3)
C8—C7—C16—C1529.2 (3)C31—C37—C46—C45103.2 (2)
C1—C7—C16—C1780.4 (2)C38—C37—C46—C47153.72 (18)
C8—C7—C16—C17152.82 (19)C31—C37—C46—C4776.1 (2)
C15—C16—C17—C18179.3 (2)C45—C46—C47—C48177.9 (2)
C7—C16—C17—C181.3 (3)C37—C46—C47—C481.4 (3)
C15—C16—C17—C222.5 (3)C45—C46—C47—C521.1 (3)
C7—C16—C17—C22179.49 (18)C37—C46—C47—C52179.57 (18)
C22—C17—C18—C190.5 (3)C52—C47—C48—C490.8 (3)
C16—C17—C18—C19178.7 (2)C46—C47—C48—C49179.8 (2)
C17—C18—C19—C200.2 (3)C47—C48—C49—C501.4 (3)
C18—C19—C20—C211.0 (3)C48—C49—C50—C511.3 (3)
C19—C20—C21—C221.1 (3)C49—C50—C51—C520.6 (3)
C20—C21—C22—C170.3 (3)C50—C51—C52—C470.0 (3)
C20—C21—C22—C23178.4 (2)C50—C51—C52—C53178.3 (2)
C18—C17—C22—C210.4 (3)C48—C47—C52—C510.1 (3)
C16—C17—C22—C21178.74 (19)C46—C47—C52—C51179.20 (19)
C18—C17—C22—C23177.63 (19)C48—C47—C52—C53178.34 (18)
C16—C17—C22—C230.7 (3)C46—C47—C52—C532.6 (3)
C24—N2—C23—N14.8 (3)C54—N4—C53—N31.9 (3)
C24—N2—C23—C22172.68 (19)C54—N4—C53—C52176.19 (19)
C15—N1—C23—N2174.92 (19)C45—N3—C53—N4176.24 (19)
C15—N1—C23—C222.6 (3)C45—N3—C53—C521.9 (3)
C21—C22—C23—N23.6 (3)C51—C52—C53—N44.0 (3)
C17—C22—C23—N2174.47 (19)C47—C52—C53—N4174.20 (19)
C21—C22—C23—N1178.78 (19)C51—C52—C53—N3177.75 (19)
C17—C22—C23—N13.1 (3)C47—C52—C53—N34.0 (3)
C23—N2—C24—O17.2 (3)C53—N4—C54—O26.1 (3)
C23—N2—C24—C25171.15 (19)C53—N4—C54—C55171.66 (18)
O1—C24—C25—C26154.9 (2)O2—C54—C55—C5623.3 (3)
N2—C24—C25—C2626.6 (3)N4—C54—C55—C56154.6 (2)
O1—C24—C25—C3026.9 (3)O2—C54—C55—C60158.2 (2)
N2—C24—C25—C30151.6 (2)N4—C54—C55—C6023.9 (3)
C30—C25—C26—C270.1 (4)C60—C55—C56—C570.2 (3)
C24—C25—C26—C27178.1 (2)C54—C55—C56—C57178.8 (2)
C25—C26—C27—C281.3 (4)C55—C56—C57—C580.1 (4)
C26—C27—C28—C291.0 (4)C56—C57—C58—C590.3 (4)
C27—C28—C29—C300.7 (4)C57—C58—C59—C600.2 (4)
C26—C25—C30—C291.8 (4)C58—C59—C60—C550.2 (4)
C24—C25—C30—C29176.4 (2)C56—C55—C60—C590.4 (4)
C28—C29—C30—C252.1 (4)C54—C55—C60—C59178.9 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C26—H26···Cg1i0.932.863.668 (2)146
C28—H28···Cg2ii0.932.763.610 (3)152
C58—H58···Cg3iii0.932.843.588 (3)138
Symmetry codes: (i) x+1/2, y, z1/2; (ii) x, y+1, z1/2; (iii) x+1/2, y, z+1/2.

Experimental details

Crystal data
Chemical formulaC30H21ClN2O
Mr460.94
Crystal system, space groupOrthorhombic, Pca21
Temperature (K)113
a, b, c (Å)26.567 (5), 9.6752 (19), 17.329 (4)
V3)4454.5 (15)
Z8
Radiation typeMo Kα
µ (mm1)0.20
Crystal size (mm)0.20 × 0.18 × 0.10
Data collection
DiffractometerRigaku Saturn724 CCD
Absorption correctionMulti-scan
(CrystalClear; Rigaku, 2009)
Tmin, Tmax0.961, 0.980
No. of measured, independent and
observed [I > 2σ(I)] reflections
27069, 8288, 7795
Rint0.038
(sin θ/λ)max1)0.618
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.040, 0.103, 1.06
No. of reflections8288
No. of parameters613
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.52, 0.47
Absolute structureFlack (1983), with how many Friedel pairs?
Absolute structure parameter0.46 (5)

Computer programs: CrystalClear (Rigaku, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C26—H26···Cg1i0.932.863.668 (2)146
C28—H28···Cg2ii0.932.763.610 (3)152
C58—H58···Cg3iii0.932.843.588 (3)138
Symmetry codes: (i) x+1/2, y, z1/2; (ii) x, y+1, z1/2; (iii) x+1/2, y, z+1/2.
 

Acknowledgements

The authors thank Jiangsu University (grant No. 09JDG064) for financial support.

References

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