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Acta Crystallogr Sect E Struct Rep Online. 2010 November 1; 66(Pt 11): o2973–o2974.
Published online 2010 October 31. doi:  10.1107/S1600536810043485
PMCID: PMC3009300

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

Abstract

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 [triangle]). For their anti­tumour activity, see: Stermitz et al. (1973 [triangle], 1975 [triangle]); Fang et al. (1993 [triangle]); Suzuki et al. (1992 [triangle]); Kanzawa et al. (1997 [triangle]); Guo et al. (2007 [triangle]); for their anti­microbial activity, see: Nissanka et al. (2001 [triangle]); for their anti inflammatory activity, see: Lenfeld et al. (1981 [triangle]); for their anti­tuberculosis activity, see: Ishikawa (2001 [triangle]). For the synthesis of the starting material, see: Zhang et al. (2008 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o2973-scheme1.jpg

Experimental

Crystal data

  • C30H21ClN2O
  • M r = 460.94
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2973-efi1.jpg
  • 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 [triangle]) T min = 0.961, T max = 0.980
  • 27069 measured reflections
  • 8288 independent reflections
  • 7795 reflections with I > 2σ(I)
  • R int = 0.038

Refinement

  • R[F 2 > 2σ(F 2)] = 0.040
  • wR(F 2) = 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 [triangle]), with 3751 Friedel pairs
  • Flack parameter: 0.46 (5)

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810043485/hg2734sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810043485/hg2734Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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

supplementary crystallographic information

Comment

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).

Experimental

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

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).

Figures

Fig. 1.
The asymmetric unit of the title compound, (I), with displacement ellipsoids drawn at the 30% probability level.
Fig. 2.
The packing diagram of the title compound. Intermolecular C—H···π interactions are shown as dashed line.

Crystal data

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

Rigaku Saturn724 CCD diffractometer8288 independent reflections
Radiation source: rotating anode7795 reflections with I > 2σ(I)
confocalRint = 0.038
ω scansθmax = 26.1°, θmin = 2.1°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2009)h = −28→32
Tmin = 0.961, Tmax = 0.980k = −11→11
27069 measured reflectionsl = −21→20

Refinement

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) = 0.103w = 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 methodsFlack parameter: 0.46 (5)

Special details

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)

xyzUiso*/Ueq
Cl10.45020 (2)1.04494 (6)0.45992 (4)0.03290 (15)
Cl2−0.18314 (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)
H270.06370.6715−0.04970.038*
C280.03835 (9)0.4848 (3)−0.01481 (15)0.0302 (6)
H280.01580.4715−0.05520.036*
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*
C31−0.03808 (7)0.6800 (2)0.21873 (13)0.0186 (4)
C32−0.06480 (8)0.6718 (2)0.28733 (14)0.0245 (5)
H32−0.05240.71600.33110.029*
C33−0.11012 (9)0.5983 (3)0.29190 (15)0.0275 (5)
H33−0.12760.59150.33830.033*
C34−0.12821 (8)0.5360 (2)0.22564 (15)0.0241 (5)
C35−0.10328 (9)0.5472 (2)0.15631 (15)0.0272 (5)
H35−0.11670.50730.11210.033*
C36−0.05835 (8)0.6178 (2)0.15263 (14)0.0237 (5)
H36−0.04130.62430.10590.028*
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*
H38B−0.00510.85350.11360.027*
C390.00102 (8)1.0040 (2)0.19526 (14)0.0220 (5)
C40−0.02315 (8)1.1084 (2)0.15437 (15)0.0271 (5)
H40−0.03091.09470.10260.032*
C41−0.03583 (9)1.2323 (3)0.18932 (17)0.0320 (6)
H41−0.05211.30070.16100.038*
C42−0.02439 (9)1.2545 (3)0.26580 (16)0.0293 (6)
H42−0.03311.33760.28930.035*
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)

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, °)

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—C3−0.7 (3)C36—C31—C32—C332.7 (3)
C7—C1—C2—C3179.5 (2)C37—C31—C32—C33−173.6 (2)
C1—C2—C3—C40.8 (3)C31—C32—C33—C34−1.3 (4)
C2—C3—C4—C5−0.5 (3)C32—C33—C34—C35−1.2 (4)
C2—C3—C4—Cl1−178.46 (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—C36−175.94 (18)
C4—C5—C6—C10.1 (3)C34—C35—C36—C31−0.8 (3)
C2—C1—C6—C50.3 (3)C32—C31—C36—C35−1.6 (3)
C7—C1—C6—C5−179.9 (2)C37—C31—C36—C35174.9 (2)
C2—C1—C7—C16154.6 (2)C32—C31—C37—C469.5 (3)
C6—C1—C7—C16−25.2 (3)C36—C31—C37—C46−166.81 (19)
C2—C1—C7—C8−80.1 (3)C32—C31—C37—C38−119.0 (2)
C6—C1—C7—C8100.1 (2)C36—C31—C37—C3864.6 (3)
C16—C7—C8—C946.6 (2)C46—C37—C38—C39−45.4 (2)
C1—C7—C8—C9−80.2 (2)C31—C37—C38—C3984.2 (2)
C7—C8—C9—C10146.8 (2)C37—C38—C39—C40−147.5 (2)
C7—C8—C9—C14−35.2 (3)C37—C38—C39—C4435.8 (3)
C14—C9—C10—C112.0 (3)C44—C39—C40—C41−1.2 (3)
C8—C9—C10—C11−179.9 (2)C38—C39—C40—C41−177.8 (2)
C9—C10—C11—C12−1.5 (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—C44−0.1 (3)
C12—C13—C14—C9−0.1 (3)C42—C43—C44—C39−0.8 (3)
C12—C13—C14—C15177.8 (2)C42—C43—C44—C45−177.9 (2)
C10—C9—C14—C13−1.2 (3)C40—C39—C44—C431.4 (3)
C8—C9—C14—C13−179.3 (2)C38—C39—C44—C43178.2 (2)
C10—C9—C14—C15−179.2 (2)C40—C39—C44—C45178.7 (2)
C8—C9—C14—C152.7 (3)C38—C39—C44—C45−4.6 (3)
C23—N1—C15—C160.6 (3)C53—N3—C45—C46−1.8 (3)
C23—N1—C15—C14−178.02 (19)C53—N3—C45—C44176.6 (2)
C13—C14—C15—C16−160.3 (2)C43—C44—C45—C46160.3 (2)
C9—C14—C15—C1617.6 (3)C39—C44—C45—C46−16.9 (3)
C13—C14—C15—N118.3 (3)C43—C44—C45—N3−18.1 (3)
C9—C14—C15—N1−163.79 (19)C39—C44—C45—N3164.72 (19)
N1—C15—C16—C17−3.2 (3)N3—C45—C46—C473.3 (3)
C14—C15—C16—C17175.35 (19)C44—C45—C46—C47−175.03 (19)
N1—C15—C16—C7178.80 (18)N3—C45—C46—C37−177.39 (18)
C14—C15—C16—C7−2.6 (3)C44—C45—C46—C374.3 (3)
C1—C7—C16—C1597.6 (2)C38—C37—C46—C4527.0 (3)
C8—C7—C16—C15−29.2 (3)C31—C37—C46—C45−103.2 (2)
C1—C7—C16—C17−80.4 (2)C38—C37—C46—C47−153.72 (18)
C8—C7—C16—C17152.82 (19)C31—C37—C46—C4776.1 (2)
C15—C16—C17—C18−179.3 (2)C45—C46—C47—C48177.9 (2)
C7—C16—C17—C18−1.3 (3)C37—C46—C47—C48−1.4 (3)
C15—C16—C17—C222.5 (3)C45—C46—C47—C52−1.1 (3)
C7—C16—C17—C22−179.49 (18)C37—C46—C47—C52179.57 (18)
C22—C17—C18—C19−0.5 (3)C52—C47—C48—C49−0.8 (3)
C16—C17—C18—C19−178.7 (2)C46—C47—C48—C49−179.8 (2)
C17—C18—C19—C20−0.2 (3)C47—C48—C49—C501.4 (3)
C18—C19—C20—C211.0 (3)C48—C49—C50—C51−1.3 (3)
C19—C20—C21—C22−1.1 (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—C53−178.3 (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—C23−177.63 (19)C48—C47—C52—C53178.34 (18)
C16—C17—C22—C230.7 (3)C46—C47—C52—C53−2.6 (3)
C24—N2—C23—N14.8 (3)C54—N4—C53—N3−1.9 (3)
C24—N2—C23—C22−172.68 (19)C54—N4—C53—C52176.19 (19)
C15—N1—C23—N2−174.92 (19)C45—N3—C53—N4176.24 (19)
C15—N1—C23—C222.6 (3)C45—N3—C53—C52−1.9 (3)
C21—C22—C23—N2−3.6 (3)C51—C52—C53—N44.0 (3)
C17—C22—C23—N2174.47 (19)C47—C52—C53—N4−174.20 (19)
C21—C22—C23—N1178.78 (19)C51—C52—C53—N3−177.75 (19)
C17—C22—C23—N1−3.1 (3)C47—C52—C53—N34.0 (3)
C23—N2—C24—O1−7.2 (3)C53—N4—C54—O26.1 (3)
C23—N2—C24—C25171.15 (19)C53—N4—C54—C55−171.66 (18)
O1—C24—C25—C26−154.9 (2)O2—C54—C55—C56−23.3 (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—C30−151.6 (2)N4—C54—C55—C60−23.9 (3)
C30—C25—C26—C270.1 (4)C60—C55—C56—C57−0.2 (3)
C24—C25—C26—C27−178.1 (2)C54—C55—C56—C57−178.8 (2)
C25—C26—C27—C281.3 (4)C55—C56—C57—C58−0.1 (4)
C26—C27—C28—C29−1.0 (4)C56—C57—C58—C590.3 (4)
C27—C28—C29—C30−0.7 (4)C57—C58—C59—C60−0.2 (4)
C26—C25—C30—C29−1.8 (4)C58—C59—C60—C55−0.2 (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, °)

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, z−1/2; (ii) −x, −y+1, z−1/2; (iii) −x+1/2, y, z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG2734).

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