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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 69| Part 12| December 2013| Pages o1839-o1840

Ethyl 6-(4-chloro­phen­yl)-4-(4-fluoro­phen­yl)-2-oxo­cyclo­hex-3-ene-1-carboxyl­ate

aDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India, bDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, cDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, and dDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA
*Correspondence e-mail: jjasinski@keene.edu

(Received 9 October 2013; accepted 22 November 2013; online 30 November 2013)

The asymmetric unit of the title compound, C21H18ClFO3, contains two independent mol­ecules. In one mol­ecule (A), the 4-chloro­phenyl, oxo­cyclo­hex-3-ene, carboxyl­ate, and ethyl groups were refined as disordered over two sets of sites with a 0.684 (5):0.316 (5) ratio. The cyclo­hexene ring in the disordered mol­ecule is in a slightly distorted envelope conformation for the major component (with the C atom bound to the carboxylate group being the flap atom) and in a screw-boat conformation for the minor component. In the ordered mol­ecule (B), the cyclo­hexene ring is in a half-chair conformation. The dihedral angles between the mean planes of the fluoro- and chloro-substituted benzene rings are 89.9 (7) (only the major component is considered for A) and 76.4 (7)° (B). In the crystal, inversion dimers are observed along with weak C—H⋯O hydrogen bonds, which form chains along [100].

Related literature

For the synthesis and applications of 4,6-diaryl-2-oxo-cyclo­hex-3-ene-1-carboxyl­ate derivatives, see: Ashalatha et al. (2009[Ashalatha, B. V., Narayana, B. & Vijaya Raj, K. K. (2009). Phosphorus Sulfur Silicon, 184, 1904-1919.]); Sreevidya et al. (2010[Sreevidya, T. V., Narayana, B. & Yathirajan, H. S. (2010). Cent. Eur. J. Chem. 8, 171-181.]); Padmavathi et al. (2000[Padmavathi, V., Reddy, B. J. M., Balaiah, A., Reddy, K. V. & Reddy, D. B. (2000). Molecules, 5, 1281-1286.]); Senguttuvan & Nagarajan (2010[Senguttuvan, S. & Nagarajan, S. (2010). Int. J. Chem. 2, 108-112.]); Butcher et al. (2011[Butcher, R. J., Akkurt, M., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2011). Acta Cryst. E67, o1346-o1347.]). For puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For standard bond lengths, see Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For related structures, see: Dutkiewicz et al. (2011a[Dutkiewicz, G., Narayana, B., Veena, K., Yathirajan, H. S. & Kubicki, M. (2011a). Acta Cryst. E67, o334-o335.],b[Dutkiewicz, G., Narayana, B., Veena, K., Yathirajan, H. S. & Kubicki, M. (2011b). Acta Cryst. E67, o336.],c[Dutkiewicz, G., Narayana, B., Veena, K., Yathirajan, H. S. & Kubicki, M. (2011c). Acta Cryst. E67, o445-o446.]); Fun et al. (2010[Fun, H.-K., Hemamalini, M., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2010). Acta Cryst. E66, o864-o865.]); Harrison et al. (2010[Harrison, W. T. A., Mayekar, A. N., Yathirajan, H. S., Narayana, B. & Sarojini, B. K. (2010). Acta Cryst. E66, o2478.]); Kant et al. (2012[Kant, R., Gupta, V. K., Kapoor, K., Sapnakumari, M., Narayana, B. & Sarojini, B. K. (2012). Acta Cryst. E68, o2917-o2918.]).

[Scheme 1]

Experimental

Crystal data
  • C21H18ClFO3

  • Mr = 372.80

  • Triclinic, [P \overline 1]

  • a = 11.6611 (5) Å

  • b = 13.1823 (5) Å

  • c = 13.2251 (5) Å

  • α = 77.250 (3)°

  • β = 87.320 (3)°

  • γ = 67.342 (4)°

  • V = 1828.15 (14) Å3

  • Z = 4

  • Cu Kα radiation

  • μ = 2.09 mm−1

  • T = 123 K

  • 0.35 × 0.23 × 0.18 mm

Data collection
  • Agilent Xcalibur (Ruby, Gemini) diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, Oxfordshire, England.]) Tmin = 0.508, Tmax = 1.000

  • 13437 measured reflections

  • 7365 independent reflections

  • 6861 reflections with I > 2σ(I)

  • Rint = 0.021

Refinement
  • R[F2 > 2σ(F2)] = 0.055

  • wR(F2) = 0.148

  • S = 1.09

  • 7365 reflections

  • 617 parameters

  • 177 restraints

  • H-atom parameters constrained

  • Δρmax = 0.68 e Å−3

  • Δρmin = −0.40 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C8A—H8A⋯O1B 0.95 2.55 3.478 (3) 167
C2A—H2AA⋯O1B 0.99 2.44 3.288 (6) 143
C2A—H2AB⋯O2Bi 0.99 2.56 3.432 (7) 147
C2C—H2CA⋯O1B 0.99 2.32 3.278 (18) 164
C2C—H2CB⋯O2Bi 0.99 2.42 3.40 (2) 170
C2B—H2BA⋯O1Aii 0.99 2.49 3.315 (8) 140
C2B—H2BA⋯O1Cii 0.99 2.56 3.380 (18) 140
C2B—H2BB⋯O2Ciii 0.99 2.58 3.436 (10) 145
C8B—H8B⋯O1Aii 0.95 2.50 3.379 (8) 154
C8B—H8B⋯O1Cii 0.95 2.54 3.417 (19) 154
C9B—H9B⋯O2Aii 0.95 2.54 3.274 (6) 134
C14B—H14B⋯O2Aiii 0.95 2.54 3.247 (5) 131
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) x, y, z+1; (iii) -x+2, -y+1, -z+1.

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, Oxfordshire, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, Oxfordshire, England.]); 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

Michael addition of ethyl acetoacetate to chalcones yield 4,6-diaryl-2-oxo-cyclohex-3-ene-1-carboxylate derivatives (Ashalatha et al., 2009; Sreevidya et al., 2010), which could be used as efficient synthons for building spiro compounds or as intermediates in the synthesis of isoxazoles, pyrazoles and quinazolins (Padmavathi et al., 2000; Senguttuvan & Nagarajan, 2010; Butcher et al., 2011). The crystal structure of some cyclohexenone derivatives, viz., methyl 4,6-bis(4-fluorophenyl)-2-oxocyclohex-3-ene-1-carboxylate (Fun et al., 2010), (1RS,6SR)-ethyl 4-(4-chlorophenyl)- 6-(4-fluorophenyl)-2-oxocyclohex-3-ene-1-carboxylate toluene hemisolvate (Dutkiewicz et al. 2011a), (1RS,6SR)-ethyl 4,6-bis(4-fluorophenyl)-2-oxocyclohex-3-ene-1-carboxylate (Dutkiewicz et al. 2011b), (1RS,6SR)-ethyl 4-(2, 4-dichlorophenyl)-6-(4-fluorophenyl)-2-oxocyclohex-3-ene- 1-carboxylate (Dutkiewicz et al. 2011c), ethyl 4-(2,4- dichlorophenyl)-6-(6-methoxy-2-naphthyl)-2-oxocyclohex-3-ene- 1-carboxylate (Harrison et al., 2010), ethyl 6-(4- chlorophenyl)-4-(4-fluorophenyl)-2-oxocyclohex-3-ene-1-carboxylate (Kant et al., 2012) have been reported. In view of the importance of cyclohexenone derivatives, the title compound, was prepared (Fig. 4) and its crystal structure is reported.

The title compound, (I), crystallizes with two independent molecules (A & B) in the asymmetric unit (Fig. 1 & 2). Disorder is modeled for the 4-chlorophyenyl and oxocyclohex-3-ene rings and carboxylate and ethyl groups in molecule A with an occupancy ratio of 0.684 (5) : 0.316 (5) (Fig. 1). The cyclohexene ring in disordered molecule A (0.684 (5) occupancy) is in a slightly distorted envelope conformation (puckering parameters, C1A–C6A: Q, θ, and ϕ = 0.477 (7)Å, 57.3 (14)° and 335.4 (15)°) while in disordered molecule C (0.316 (5) occupancy) it is in a screw-boat conformation (C1C–C6C: 0.579 (17)Å, 112 (2)° and 154 (2)°. In molecule B the cyclohexene ring is in a half-chair conformation (puckering parameters, C1B–C6B: Q, θ, and ϕ = 0.477 (2) Å, 50.6 (3))° and 356.2 (4)°), respectively, (Cremer & Pople, 1975) (Fig. 2). Bond lengths are in normal ranges (Allen et al., 1987). The dihedral angle between the mean planes of the 4-fluorophenyl and 4-chlorophenyl rings is 89.9 (7)° (molecule A) and 76.4 (7)° (molecule B), respectively. In the crystal, weak C—H···O intermolecular interactions are observed (Table 1) forming chains along [100] and which contribute to packing stability (Fig. 3).

Related literature top

For the synthesis and applications of 4,6-diaryl-2-oxo-cyclohex-3- ene-1-carboxylate derivatives, see: Ashalatha et al. (2009); Sreevidya et al. (2010); Padmavathi et al. (2000); Senguttuvan & Nagarajan (2010); Butcher et al. (2011). For puckering parameters, see: Cremer & Pople (1975). For standard bond lengths, see Allen et al. (1987). For related structures, see: Dutkiewicz et al. (2011a,b,c); Fun et al. (2010); Harrison et al. (2010); Kant et al. (2012).

Experimental top

(2E)-3-(4-Chlorophenyl)-1-(4-fluorophenyl)prop-2-en-1-one (2.60 g, 0.01 mol) and ethyl acetoacetate (1.30 g, 0.01 mol) were refluxed for 8 hrs in 30 ml absolute alcohol in presence 10% NaOH (Fig.4). The reaction mixture was cooled to room temperature and the precipitate obtained was filtered. Single crystals were grown by slow evaporation from the solvent absolute alcohol (M.P.: 412–414 K).

Refinement top

All of the H atoms were placed in their calculated positions and then refined using the riding model with Atom—H lengths of 0.95Å (CH), 0.99Å (CH2) 0.96Å or (CH3). Isotropic displacement parameters for these atoms were set to 1.2 (CH, CH2) or 1.5 (CH3) times Ueq of the parent atom. Idealised Me refined as rotating groups. Disorder was modeled for the chloro (Cl1A, Cl1C) and ethyl (C20A, C20C, C21A, C12C) groups as well as the cyclohexane ring (C1A, C1C, C2A, C2C, C3A, C3C, C4A, C4C, C5A, C5C, C6A, C6C) and carboxylate groups in molecule A with an occupancy ratio of 0.684 (5) : 0.316 (5).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis RED (Agilent, 2012); 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 molecular structure of molecule A in (I) showing 30% probability displacement ellipsoids. Disorder (shown as open bonds) is modeled for the 4-chlorophyenyl and oxocyclohex-3-ene rings and carboxylate and ethyl groups, with an occupancy ratio of 0.684 (5) : 0.316 (5).
[Figure 2] Fig. 2. The molecular structure of molecule B in (I) showing 30% probability displacement ellipsoids.
[Figure 3] Fig. 3. Partial packing plot for (I) viewed along the c axis. Dashed lines indicate weak C—H···O intermolecular interactions forming chains along [100]. H atoms not involved in these weak intermolecular interactions have been removed for clarity.
[Figure 4] Fig. 4. Synthesis scheme for (I).
Ethyl 6-(4-chlorophenyl)-4-(4-fluorophenyl)-2-oxocyclohex-3-ene-1-carboxylate top
Crystal data top
C21H18ClFO3Z = 4
Mr = 372.80F(000) = 776
Triclinic, P1Dx = 1.354 Mg m3
a = 11.6611 (5) ÅCu Kα radiation, λ = 1.54178 Å
b = 13.1823 (5) ÅCell parameters from 6709 reflections
c = 13.2251 (5) Åθ = 3.4–75.5°
α = 77.250 (3)°µ = 2.09 mm1
β = 87.320 (3)°T = 123 K
γ = 67.342 (4)°Prism, colourless
V = 1828.15 (14) Å30.35 × 0.23 × 0.18 mm
Data collection top
Agilent Xcalibur (Ruby, Gemini)
diffractometer
6861 reflections with I > 2σ(I)
Detector resolution: 10.5081 pixels mm-1Rint = 0.021
ω scansθmax = 75.7°, θmin = 3.4°
Absorption correction: multi-scan
(CrysAlis PRO and CrysAlis RED; Agilent, 2012)
h = 1413
Tmin = 0.508, Tmax = 1.000k = 1613
13437 measured reflectionsl = 1612
7365 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.055H-atom parameters constrained
wR(F2) = 0.148 w = 1/[σ2(Fo2) + (0.0631P)2 + 1.2352P]
where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max < 0.001
7365 reflectionsΔρmax = 0.68 e Å3
617 parametersΔρmin = 0.40 e Å3
177 restraints
Crystal data top
C21H18ClFO3γ = 67.342 (4)°
Mr = 372.80V = 1828.15 (14) Å3
Triclinic, P1Z = 4
a = 11.6611 (5) ÅCu Kα radiation
b = 13.1823 (5) ŵ = 2.09 mm1
c = 13.2251 (5) ÅT = 123 K
α = 77.250 (3)°0.35 × 0.23 × 0.18 mm
β = 87.320 (3)°
Data collection top
Agilent Xcalibur (Ruby, Gemini)
diffractometer
7365 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO and CrysAlis RED; Agilent, 2012)
6861 reflections with I > 2σ(I)
Tmin = 0.508, Tmax = 1.000Rint = 0.021
13437 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.055177 restraints
wR(F2) = 0.148H-atom parameters constrained
S = 1.09Δρmax = 0.68 e Å3
7365 reflectionsΔρmin = 0.40 e Å3
617 parameters
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
F1A0.40903 (18)0.18316 (15)0.39705 (12)0.0598 (4)
C7A0.55724 (18)0.41724 (17)0.26781 (15)0.0298 (4)
C8A0.5667 (2)0.37490 (19)0.37517 (16)0.0347 (4)
H8A0.60720.40080.41840.042*
C9A0.5176 (2)0.2955 (2)0.41917 (17)0.0418 (5)
H9A0.52540.26580.49190.050*
C10A0.4575 (2)0.2607 (2)0.35531 (19)0.0409 (5)
C11A0.4429 (2)0.3018 (2)0.24975 (18)0.0381 (5)
H11A0.39930.27730.20780.046*
C12A0.4937 (2)0.38005 (18)0.20622 (16)0.0336 (4)
H12A0.48530.40900.13330.040*
C13A0.6987 (4)0.7320 (5)0.2915 (6)0.0352 (12)0.684 (5)
C14A0.5941 (4)0.8237 (6)0.3060 (7)0.0375 (10)0.684 (5)
H14A0.51500.83520.27860.045*0.684 (5)
C15A0.6050 (5)0.8986 (7)0.3605 (8)0.0410 (14)0.684 (5)
H15A0.53350.96130.37040.049*0.684 (5)
C16A0.7207 (5)0.8818 (6)0.4005 (8)0.0376 (13)0.684 (5)
C17A0.8253 (4)0.7901 (6)0.3860 (6)0.0403 (10)0.684 (5)
H17A0.90440.77860.41340.048*0.684 (5)
C18A0.8144 (4)0.7152 (4)0.3315 (5)0.0390 (11)0.684 (5)
H18A0.88590.65250.32160.047*0.684 (5)
C13C0.6632 (8)0.7550 (10)0.2832 (12)0.0214 (16)0.316 (5)
C14C0.5752 (8)0.8455 (13)0.3173 (15)0.0339 (19)0.316 (5)
H14C0.48990.87060.29710.041*0.316 (5)
C15C0.6120 (11)0.8994 (15)0.3810 (17)0.038 (2)0.316 (5)
H15C0.55190.96130.40440.046*0.316 (5)
C16C0.7368 (12)0.8628 (15)0.4106 (17)0.041 (3)0.316 (5)
C17C0.8248 (9)0.7722 (14)0.3765 (16)0.045 (3)0.316 (5)
H17C0.91010.74720.39670.054*0.316 (5)
C18C0.7880 (8)0.7183 (11)0.3127 (12)0.036 (2)0.316 (5)
H18C0.84810.65650.28940.043*0.316 (5)
O1A0.7088 (8)0.6061 (9)0.0287 (5)0.039 (2)0.684 (5)
O2A0.8622 (4)0.7464 (5)0.0453 (4)0.0443 (9)0.684 (5)
O3A0.6551 (4)0.8353 (4)0.0286 (5)0.0460 (9)0.684 (5)
C1A0.6422 (4)0.6813 (3)0.2171 (2)0.0323 (7)0.684 (5)
H1A0.55980.73780.18560.039*0.684 (5)
C2A0.6284 (5)0.5752 (5)0.2825 (5)0.0254 (11)0.684 (5)
H2AA0.70080.53440.33230.030*0.684 (5)
H2AB0.55290.59850.32330.030*0.684 (5)
C3A0.6191 (10)0.4952 (7)0.2200 (6)0.0232 (17)0.684 (5)
C4A0.6432 (19)0.5094 (11)0.1178 (8)0.033 (3)0.684 (5)
H4A0.62470.46500.07860.040*0.684 (5)
C5A0.6963 (16)0.5895 (10)0.0651 (6)0.031 (2)0.684 (5)
C6A0.7355 (4)0.6512 (3)0.1330 (2)0.0323 (7)0.684 (5)
H6A0.81640.59710.16910.039*0.684 (5)
C19A0.7606 (5)0.7482 (7)0.0639 (9)0.0326 (13)0.684 (5)
C20A0.6677 (5)0.9329 (3)0.0439 (3)0.0526 (10)0.684 (5)
H20A0.74430.94140.02530.063*0.684 (5)
H20B0.59571.00260.03900.063*0.684 (5)
C21A0.6735 (5)0.9152 (4)0.1535 (3)0.0620 (12)0.684 (5)
H21A0.68180.98000.20160.093*0.684 (5)
H21B0.59720.90760.17180.093*0.684 (5)
H21C0.74540.84660.15820.093*0.684 (5)
Cl1A0.7356 (3)0.9740 (2)0.4685 (2)0.0659 (7)0.684 (5)
O1C0.707 (2)0.609 (2)0.0248 (11)0.046 (5)0.316 (5)
O2C0.8488 (8)0.7264 (10)0.0760 (8)0.0437 (19)0.316 (5)
O3C0.6643 (10)0.8545 (9)0.0056 (10)0.046 (2)0.316 (5)
C1C0.7108 (6)0.6376 (5)0.2355 (4)0.0224 (11)0.316 (5)
H1C0.80200.59080.24460.027*0.316 (5)
C2C0.6260 (19)0.5767 (16)0.2845 (12)0.045 (4)0.316 (5)
H2CA0.66740.52340.34960.054*0.316 (5)
H2CB0.54790.63320.30290.054*0.316 (5)
C3C0.593 (2)0.5124 (13)0.2163 (12)0.017 (3)0.316 (5)
C4C0.640 (4)0.511 (2)0.1206 (16)0.027 (6)0.316 (5)
H4C0.65210.44860.09030.033*0.316 (5)
C5C0.672 (3)0.604 (2)0.0641 (12)0.026 (4)0.316 (5)
C6C0.6624 (6)0.6939 (5)0.1230 (4)0.0215 (12)0.316 (5)
H6C0.57350.74650.12240.026*0.316 (5)
C19C0.7385 (9)0.7589 (13)0.0677 (19)0.030 (2)0.316 (5)
C20C0.7380 (9)0.9112 (7)0.0596 (7)0.052 (2)0.316 (5)
H20C0.79820.86040.09960.062*0.316 (5)
H20D0.78340.93800.01710.062*0.316 (5)
C21C0.6394 (13)1.0084 (12)0.1302 (11)0.106 (6)0.316 (5)
H21D0.67791.05540.17470.159*0.316 (5)
H21E0.57751.05370.08830.159*0.316 (5)
H21F0.59870.97940.17340.159*0.316 (5)
Cl1C0.7756 (6)0.9386 (5)0.4862 (5)0.0558 (11)0.316 (5)
Cl1B0.71926 (7)0.05408 (6)1.16767 (5)0.05522 (19)
F1B1.15955 (14)0.76617 (13)0.77809 (13)0.0508 (4)
O1B0.75978 (18)0.44532 (17)0.51477 (12)0.0490 (4)
O2B0.66040 (19)0.2488 (2)0.66133 (17)0.0602 (5)
O3B0.86198 (17)0.20485 (17)0.63467 (17)0.0551 (5)
C1B0.8480 (2)0.33555 (18)0.78861 (16)0.0326 (4)
H1B0.93150.28670.76870.039*
C2B0.86005 (19)0.44019 (17)0.81283 (15)0.0298 (4)
H2BA0.78210.48430.84260.036*
H2BB0.92830.41550.86570.036*
C3B0.88570 (19)0.51490 (17)0.71829 (16)0.0298 (4)
C4B0.8495 (2)0.51634 (19)0.62257 (16)0.0342 (4)
H4B0.86450.56680.56520.041*
C5B0.7886 (2)0.44449 (19)0.60262 (16)0.0348 (4)
C6B0.7566 (2)0.37018 (18)0.69533 (16)0.0328 (4)
H6B0.67180.41440.71660.039*
C7B0.95342 (19)0.58550 (17)0.73334 (16)0.0308 (4)
C8B0.9539 (2)0.61594 (19)0.82868 (17)0.0354 (4)
H8B0.90680.59400.88350.042*
C9B1.0224 (2)0.6777 (2)0.84368 (19)0.0400 (5)
H9B1.02260.69830.90810.048*
C10B1.0901 (2)0.70842 (19)0.76335 (19)0.0387 (4)
C11B1.0919 (2)0.68128 (19)0.66812 (18)0.0379 (4)
H11B1.13870.70430.61370.046*
C12B1.0233 (2)0.61943 (18)0.65422 (17)0.0345 (4)
H12B1.02390.59960.58930.041*
C13B0.8118 (2)0.26734 (18)0.88381 (16)0.0321 (4)
C14B0.9047 (2)0.1782 (2)0.94658 (17)0.0387 (4)
H14B0.98900.16120.92920.046*
C15B0.8772 (2)0.1132 (2)1.03424 (19)0.0433 (5)
H15B0.94200.05251.07670.052*
C16B0.7550 (2)0.13739 (19)1.05912 (17)0.0378 (4)
C17B0.6602 (2)0.2265 (2)0.99981 (19)0.0440 (5)
H17B0.57610.24381.01820.053*
C18B0.6900 (2)0.2909 (2)0.91231 (19)0.0427 (5)
H18B0.62500.35270.87100.051*
C19B0.7517 (2)0.2683 (2)0.66292 (17)0.0375 (5)
C20B0.8715 (4)0.1043 (2)0.6009 (3)0.0696 (9)
H20E0.78710.10700.58890.083*
H20F0.91450.10160.53460.083*
C21B0.9387 (5)0.0056 (3)0.6773 (4)0.0896 (13)
H21G0.94430.06130.65340.134*
H21H0.89540.00790.74260.134*
H21I1.02260.00260.68840.134*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F1A0.0891 (12)0.0722 (11)0.0449 (8)0.0633 (10)0.0047 (8)0.0074 (7)
C7A0.0313 (10)0.0315 (9)0.0305 (10)0.0139 (8)0.0003 (7)0.0113 (8)
C8A0.0403 (11)0.0430 (11)0.0294 (10)0.0232 (9)0.0006 (8)0.0113 (8)
C9A0.0529 (13)0.0518 (13)0.0297 (10)0.0312 (11)0.0008 (9)0.0068 (9)
C10A0.0513 (13)0.0442 (12)0.0399 (12)0.0322 (11)0.0054 (10)0.0095 (9)
C11A0.0458 (12)0.0422 (11)0.0369 (11)0.0252 (10)0.0013 (9)0.0138 (9)
C12A0.0413 (11)0.0364 (10)0.0293 (10)0.0193 (9)0.0014 (8)0.0105 (8)
C13A0.050 (3)0.041 (3)0.028 (2)0.029 (2)0.008 (3)0.015 (3)
C14A0.043 (2)0.052 (3)0.032 (3)0.0284 (19)0.007 (2)0.020 (2)
C15A0.054 (2)0.044 (2)0.034 (4)0.0249 (17)0.0059 (17)0.0169 (19)
C16A0.065 (3)0.042 (3)0.023 (2)0.0368 (17)0.0041 (19)0.012 (2)
C17A0.053 (2)0.048 (2)0.034 (3)0.0334 (17)0.0010 (19)0.0107 (18)
C18A0.046 (2)0.042 (2)0.038 (3)0.0242 (18)0.003 (2)0.015 (2)
C13C0.022 (4)0.022 (4)0.022 (3)0.010 (3)0.003 (3)0.006 (3)
C14C0.045 (3)0.040 (5)0.029 (5)0.021 (3)0.016 (4)0.027 (4)
C15C0.060 (4)0.048 (5)0.025 (7)0.033 (4)0.015 (3)0.024 (4)
C16C0.064 (4)0.044 (6)0.040 (8)0.044 (4)0.011 (5)0.017 (6)
C17C0.049 (4)0.056 (7)0.049 (6)0.033 (4)0.007 (4)0.025 (5)
C18C0.032 (3)0.048 (4)0.034 (5)0.016 (3)0.016 (4)0.016 (3)
O1A0.046 (4)0.054 (5)0.028 (2)0.026 (3)0.004 (2)0.016 (3)
O2A0.0440 (16)0.057 (2)0.043 (3)0.0312 (13)0.0039 (15)0.0099 (17)
O3A0.0471 (15)0.038 (2)0.056 (2)0.0202 (15)0.0004 (15)0.0083 (13)
C1A0.0406 (19)0.0360 (16)0.0286 (14)0.0215 (15)0.0030 (12)0.0116 (11)
C2A0.024 (2)0.028 (2)0.0242 (19)0.0085 (19)0.0038 (18)0.0080 (15)
C3A0.013 (4)0.021 (2)0.0300 (18)0.000 (3)0.0071 (18)0.0074 (15)
C4A0.041 (9)0.035 (5)0.031 (3)0.018 (5)0.001 (5)0.015 (4)
C5A0.033 (7)0.036 (3)0.0280 (17)0.014 (4)0.0021 (17)0.0123 (15)
C6A0.0381 (19)0.0385 (15)0.0288 (13)0.0208 (15)0.0016 (11)0.0129 (10)
C19A0.041 (2)0.039 (2)0.026 (2)0.0209 (18)0.001 (2)0.0118 (19)
C20A0.059 (3)0.0339 (17)0.064 (2)0.0195 (19)0.004 (2)0.0062 (15)
C21A0.079 (3)0.050 (2)0.0546 (18)0.030 (2)0.020 (2)0.0083 (17)
Cl1A0.112 (2)0.0687 (14)0.0535 (11)0.0643 (14)0.0104 (11)0.0329 (11)
O1C0.090 (13)0.046 (10)0.019 (5)0.043 (9)0.007 (6)0.012 (5)
O2C0.038 (3)0.062 (5)0.046 (6)0.035 (3)0.015 (3)0.013 (4)
O3C0.063 (4)0.046 (4)0.044 (5)0.039 (3)0.009 (3)0.004 (2)
C1C0.016 (3)0.026 (3)0.026 (2)0.006 (2)0.004 (2)0.0111 (18)
C2C0.086 (12)0.051 (8)0.027 (4)0.053 (9)0.015 (7)0.019 (5)
C3C0.003 (7)0.018 (5)0.024 (4)0.003 (5)0.005 (3)0.007 (3)
C4C0.028 (15)0.038 (9)0.024 (7)0.019 (11)0.000 (9)0.012 (7)
C5C0.026 (11)0.033 (6)0.024 (3)0.013 (8)0.002 (4)0.012 (3)
C6C0.013 (3)0.028 (3)0.024 (2)0.006 (2)0.0021 (18)0.0106 (17)
C19C0.036 (4)0.040 (4)0.027 (4)0.023 (3)0.012 (4)0.020 (3)
C20C0.066 (6)0.045 (4)0.049 (4)0.027 (4)0.016 (4)0.010 (3)
C21C0.105 (9)0.090 (10)0.087 (9)0.028 (7)0.000 (7)0.040 (7)
Cl1C0.081 (3)0.062 (3)0.052 (2)0.047 (2)0.0040 (16)0.031 (2)
Cl1B0.0809 (5)0.0581 (4)0.0389 (3)0.0437 (4)0.0089 (3)0.0049 (3)
F1B0.0528 (8)0.0499 (8)0.0685 (10)0.0334 (7)0.0044 (7)0.0258 (7)
O1B0.0697 (12)0.0654 (11)0.0292 (7)0.0419 (10)0.0028 (7)0.0146 (7)
O2B0.0589 (11)0.0798 (14)0.0713 (13)0.0472 (11)0.0159 (10)0.0402 (11)
O3B0.0458 (10)0.0546 (11)0.0733 (13)0.0136 (8)0.0072 (9)0.0396 (10)
C1B0.0375 (10)0.0359 (10)0.0316 (9)0.0186 (8)0.0025 (7)0.0126 (7)
C2B0.0351 (10)0.0331 (9)0.0271 (8)0.0168 (8)0.0020 (7)0.0106 (7)
C3B0.0314 (9)0.0306 (9)0.0305 (9)0.0126 (7)0.0007 (7)0.0111 (7)
C4B0.0421 (11)0.0386 (11)0.0277 (9)0.0209 (9)0.0005 (8)0.0084 (8)
C5B0.0408 (11)0.0416 (11)0.0284 (8)0.0196 (9)0.0008 (8)0.0131 (8)
C6B0.0351 (10)0.0393 (11)0.0311 (8)0.0184 (8)0.0003 (7)0.0144 (7)
C7B0.0335 (10)0.0296 (9)0.0326 (9)0.0137 (8)0.0016 (7)0.0103 (7)
C8B0.0388 (11)0.0392 (11)0.0364 (10)0.0196 (9)0.0033 (8)0.0168 (9)
C9B0.0422 (12)0.0442 (12)0.0451 (11)0.0214 (9)0.0031 (9)0.0240 (10)
C10B0.0378 (11)0.0326 (10)0.0527 (12)0.0176 (9)0.0018 (9)0.0152 (9)
C11B0.0403 (11)0.0350 (11)0.0432 (10)0.0199 (9)0.0019 (9)0.0080 (9)
C12B0.0394 (11)0.0358 (10)0.0331 (9)0.0183 (8)0.0003 (8)0.0096 (8)
C13B0.0397 (10)0.0356 (9)0.0309 (9)0.0217 (8)0.0032 (7)0.0127 (7)
C14B0.0364 (10)0.0474 (12)0.0361 (10)0.0200 (9)0.0028 (8)0.0085 (8)
C15B0.0473 (11)0.0434 (12)0.0374 (11)0.0179 (10)0.0046 (9)0.0032 (8)
C16B0.0545 (11)0.0403 (11)0.0304 (10)0.0301 (9)0.0026 (8)0.0097 (7)
C17B0.0417 (11)0.0523 (13)0.0427 (11)0.0228 (9)0.0045 (9)0.0120 (9)
C18B0.0392 (10)0.0426 (12)0.0430 (11)0.0145 (9)0.0019 (9)0.0044 (9)
C19B0.0482 (12)0.0447 (12)0.0317 (10)0.0264 (10)0.0002 (9)0.0161 (9)
C20B0.085 (2)0.0450 (15)0.077 (2)0.0085 (15)0.0216 (17)0.0350 (15)
C21B0.118 (3)0.0538 (19)0.094 (3)0.028 (2)0.028 (2)0.0130 (18)
Geometric parameters (Å, º) top
F1A—C10A1.355 (3)C1C—C2C1.537 (6)
C7A—C8A1.399 (3)C1C—C6C1.533 (5)
C7A—C12A1.402 (3)C2C—H2CA0.9900
C7A—C3A1.490 (4)C2C—H2CB0.9900
C7A—C3C1.491 (5)C2C—C3C1.513 (5)
C8A—H8A0.9500C3C—C4C1.355 (6)
C8A—C9A1.387 (3)C4C—H4C0.9500
C9A—H9A0.9500C4C—C5C1.456 (6)
C9A—C10A1.374 (3)C5C—C6C1.526 (6)
C10A—C11A1.374 (3)C6C—H6C1.0000
C11A—H11A0.9500C6C—C19C1.518 (5)
C11A—C12A1.387 (3)C20C—H20C0.9900
C12A—H12A0.9500C20C—H20D0.9900
C13A—C14A1.3900C20C—C21C1.508 (7)
C13A—C18A1.3900C21C—H21D0.9800
C13A—C1A1.593 (4)C21C—H21E0.9800
C14A—H14A0.9500C21C—H21F0.9800
C14A—C15A1.3900Cl1B—C16B1.744 (2)
C15A—H15A0.9500F1B—C10B1.352 (2)
C15A—C16A1.3900O1B—C5B1.221 (3)
C16A—C17A1.3900O2B—C19B1.189 (3)
C16A—Cl1A1.724 (3)O3B—C19B1.326 (3)
C17A—H17A0.9500O3B—C20B1.453 (3)
C17A—C18A1.3900C1B—H1B1.0000
C18A—H18A0.9500C1B—C2B1.541 (3)
C13C—C14C1.3900C1B—C6B1.538 (3)
C13C—C18C1.3900C1B—C13B1.522 (3)
C13C—C1C1.684 (9)C2B—H2BA0.9900
C14C—H14C0.9500C2B—H2BB0.9900
C14C—C15C1.3900C2B—C3B1.507 (3)
C15C—H15C0.9500C3B—C4B1.347 (3)
C15C—C16C1.3900C3B—C7B1.481 (3)
C16C—C17C1.3900C4B—H4B0.9500
C16C—Cl1C1.742 (7)C4B—C5B1.456 (3)
C17C—H17C0.9500C5B—C6B1.520 (3)
C17C—C18C1.3900C6B—H6B1.0000
C18C—H18C0.9500C6B—C19B1.519 (3)
O1A—C5A1.224 (5)C7B—C8B1.406 (3)
O2A—C19A1.190 (5)C7B—C12B1.398 (3)
O3A—C19A1.333 (5)C8B—H8B0.9500
O3A—C20A1.478 (5)C8B—C9B1.388 (3)
C1A—H1A1.0000C9B—H9B0.9500
C1A—C2A1.536 (4)C9B—C10B1.376 (3)
C1A—C6A1.525 (4)C10B—C11B1.380 (3)
C2A—H2AA0.9900C11B—H11B0.9500
C2A—H2AB0.9900C11B—C12B1.385 (3)
C2A—C3A1.513 (4)C12B—H12B0.9500
C3A—C4A1.354 (5)C13B—C14B1.384 (3)
C4A—H4A0.9500C13B—C18B1.385 (3)
C4A—C5A1.455 (5)C14B—H14B0.9500
C5A—C6A1.525 (6)C14B—C15B1.385 (3)
C6A—H6A1.0000C15B—H15B0.9500
C6A—C19A1.519 (4)C15B—C16B1.376 (4)
C20A—H20A0.9900C16B—C17B1.375 (4)
C20A—H20B0.9900C17B—H17B0.9500
C20A—C21A1.513 (6)C17B—C18B1.391 (3)
C21A—H21A0.9800C18B—H18B0.9500
C21A—H21B0.9800C20B—H20E0.9900
C21A—H21C0.9800C20B—H20F0.9900
O1C—C5C1.224 (6)C20B—C21B1.427 (5)
O2C—C19C1.191 (6)C21B—H21G0.9800
O3C—C19C1.334 (6)C21B—H21H0.9800
O3C—C20C1.477 (6)C21B—H21I0.9800
C1C—H1C1.0000
C8A—C7A—C12A118.40 (19)C3C—C2C—H2CB108.5
C8A—C7A—C3A120.5 (4)C7A—C3C—C2C118.0 (9)
C8A—C7A—C3C123.7 (7)C4C—C3C—C7A117.5 (11)
C12A—C7A—C3A121.0 (4)C4C—C3C—C2C119.9 (10)
C12A—C7A—C3C117.2 (7)C3C—C4C—H4C119.9
C7A—C8A—H8A119.6C3C—C4C—C5C120.2 (13)
C9A—C8A—C7A120.72 (19)C5C—C4C—H4C119.9
C9A—C8A—H8A119.6O1C—C5C—C4C122.1 (13)
C8A—C9A—H9A120.7O1C—C5C—C6C121.6 (13)
C10A—C9A—C8A118.6 (2)C4C—C5C—C6C116.3 (11)
C10A—C9A—H9A120.7C1C—C6C—H6C109.3
F1A—C10A—C9A119.4 (2)C5C—C6C—C1C109.5 (11)
F1A—C10A—C11A117.7 (2)C5C—C6C—H6C109.3
C9A—C10A—C11A122.9 (2)C19C—C6C—C1C111.4 (9)
C10A—C11A—H11A121.0C19C—C6C—C5C107.9 (13)
C10A—C11A—C12A118.1 (2)C19C—C6C—H6C109.3
C12A—C11A—H11A121.0O2C—C19C—O3C125.5 (8)
C7A—C12A—H12A119.4O2C—C19C—C6C124.4 (8)
C11A—C12A—C7A121.2 (2)O3C—C19C—C6C110.1 (7)
C11A—C12A—H12A119.4O3C—C20C—H20C111.3
C14A—C13A—C18A120.0O3C—C20C—H20D111.3
C14A—C13A—C1A101.1 (3)O3C—C20C—C21C102.4 (8)
C18A—C13A—C1A138.6 (3)H20C—C20C—H20D109.2
C13A—C14A—H14A120.0C21C—C20C—H20C111.3
C15A—C14A—C13A120.0C21C—C20C—H20D111.3
C15A—C14A—H14A120.0C20C—C21C—H21D109.5
C14A—C15A—H15A120.0C20C—C21C—H21E109.5
C14A—C15A—C16A120.0C20C—C21C—H21F109.5
C16A—C15A—H15A120.0H21D—C21C—H21E109.5
C15A—C16A—C17A120.0H21D—C21C—H21F109.5
C15A—C16A—Cl1A120.5 (2)H21E—C21C—H21F109.5
C17A—C16A—Cl1A119.5 (2)C19B—O3B—C20B117.5 (2)
C16A—C17A—H17A120.0C2B—C1B—H1B107.6
C16A—C17A—C18A120.0C6B—C1B—H1B107.6
C18A—C17A—H17A120.0C6B—C1B—C2B110.35 (17)
C13A—C18A—H18A120.0C13B—C1B—H1B107.6
C17A—C18A—C13A120.0C13B—C1B—C2B111.21 (16)
C17A—C18A—H18A120.0C13B—C1B—C6B112.24 (17)
C14C—C13C—C18C120.0C1B—C2B—H2BA109.0
C14C—C13C—C1C154.5 (6)C1B—C2B—H2BB109.0
C18C—C13C—C1C84.1 (5)H2BA—C2B—H2BB107.8
C13C—C14C—H14C120.0C3B—C2B—C1B112.74 (16)
C13C—C14C—C15C120.0C3B—C2B—H2BA109.0
C15C—C14C—H14C120.0C3B—C2B—H2BB109.0
C14C—C15C—H15C120.0C4B—C3B—C2B120.95 (18)
C16C—C15C—C14C120.0C4B—C3B—C7B120.86 (19)
C16C—C15C—H15C120.0C7B—C3B—C2B118.18 (17)
C15C—C16C—C17C120.0C3B—C4B—H4B118.4
C15C—C16C—Cl1C117.0 (6)C3B—C4B—C5B123.3 (2)
C17C—C16C—Cl1C123.0 (6)C5B—C4B—H4B118.4
C16C—C17C—H17C120.0O1B—C5B—C4B121.9 (2)
C16C—C17C—C18C120.0O1B—C5B—C6B120.09 (19)
C18C—C17C—H17C120.0C4B—C5B—C6B117.97 (17)
C13C—C18C—H18C120.0C1B—C6B—H6B107.9
C17C—C18C—C13C120.0C5B—C6B—C1B112.02 (17)
C17C—C18C—H18C120.0C5B—C6B—H6B107.9
C19A—O3A—C20A116.4 (4)C19B—C6B—C1B111.75 (18)
C13A—C1A—H1A110.6C19B—C6B—C5B109.21 (17)
C2A—C1A—C13A107.7 (4)C19B—C6B—H6B107.9
C2A—C1A—H1A110.6C8B—C7B—C3B121.13 (19)
C6A—C1A—C13A106.7 (3)C12B—C7B—C3B120.62 (18)
C6A—C1A—H1A110.6C12B—C7B—C8B118.19 (19)
C6A—C1A—C2A110.6 (4)C7B—C8B—H8B119.6
C1A—C2A—H2AA108.7C9B—C8B—C7B120.7 (2)
C1A—C2A—H2AB108.7C9B—C8B—H8B119.6
H2AA—C2A—H2AB107.6C8B—C9B—H9B120.7
C3A—C2A—C1A114.3 (3)C10B—C9B—C8B118.7 (2)
C3A—C2A—H2AA108.7C10B—C9B—H9B120.7
C3A—C2A—H2AB108.7F1B—C10B—C9B119.1 (2)
C7A—C3A—C2A117.5 (5)F1B—C10B—C11B118.2 (2)
C4A—C3A—C7A120.6 (6)C9B—C10B—C11B122.8 (2)
C4A—C3A—C2A120.6 (4)C10B—C11B—H11B121.0
C3A—C4A—H4A118.4C10B—C11B—C12B118.0 (2)
C3A—C4A—C5A123.3 (7)C12B—C11B—H11B121.0
C5A—C4A—H4A118.4C7B—C12B—H12B119.2
O1A—C5A—C4A121.7 (7)C11B—C12B—C7B121.6 (2)
O1A—C5A—C6A121.8 (7)C11B—C12B—H12B119.2
C4A—C5A—C6A116.5 (6)C14B—C13B—C1B118.9 (2)
C1A—C6A—H6A106.9C14B—C13B—C18B117.8 (2)
C5A—C6A—C1A110.4 (5)C18B—C13B—C1B123.3 (2)
C5A—C6A—H6A106.9C13B—C14B—H14B119.3
C19A—C6A—C1A116.2 (5)C13B—C14B—C15B121.4 (2)
C19A—C6A—C5A109.0 (6)C15B—C14B—H14B119.3
C19A—C6A—H6A106.9C14B—C15B—H15B120.4
O2A—C19A—O3A124.9 (4)C16B—C15B—C14B119.3 (2)
O2A—C19A—C6A123.7 (4)C16B—C15B—H15B120.4
O3A—C19A—C6A111.4 (4)C15B—C16B—Cl1B119.63 (19)
O3A—C20A—H20A109.8C17B—C16B—Cl1B119.30 (19)
O3A—C20A—H20B109.8C17B—C16B—C15B121.1 (2)
O3A—C20A—C21A109.5 (4)C16B—C17B—H17B120.7
H20A—C20A—H20B108.2C16B—C17B—C18B118.7 (2)
C21A—C20A—H20A109.8C18B—C17B—H17B120.7
C21A—C20A—H20B109.8C13B—C18B—C17B121.7 (2)
C20A—C21A—H21A109.5C13B—C18B—H18B119.1
C20A—C21A—H21B109.5C17B—C18B—H18B119.1
C20A—C21A—H21C109.5O2B—C19B—O3B124.3 (2)
H21A—C21A—H21B109.5O2B—C19B—C6B124.5 (2)
H21A—C21A—H21C109.5O3B—C19B—C6B111.16 (19)
H21B—C21A—H21C109.5O3B—C20B—H20E109.6
C19C—O3C—C20C110.8 (8)O3B—C20B—H20F109.6
C13C—C1C—H1C115.3H20E—C20B—H20F108.1
C2C—C1C—C13C104.3 (10)C21B—C20B—O3B110.5 (3)
C2C—C1C—H1C115.3C21B—C20B—H20E109.6
C6C—C1C—C13C97.9 (6)C21B—C20B—H20F109.6
C6C—C1C—H1C115.3C20B—C21B—H21G109.5
C6C—C1C—C2C107.0 (8)C20B—C21B—H21H109.5
C1C—C2C—H2CA108.5C20B—C21B—H21I109.5
C1C—C2C—H2CB108.5H21G—C21B—H21H109.5
H2CA—C2C—H2CB107.5H21G—C21B—H21I109.5
C3C—C2C—C1C114.9 (8)H21H—C21B—H21I109.5
C3C—C2C—H2CA108.5
F1A—C10A—C11A—C12A179.1 (2)C1C—C13C—C18C—C17C171.2 (11)
C7A—C8A—C9A—C10A1.1 (4)C1C—C2C—C3C—C7A156.1 (14)
C7A—C3A—C4A—C5A176.1 (14)C1C—C2C—C3C—C4C1 (3)
C7A—C3C—C4C—C5C177 (3)C1C—C6C—C19C—O2C41 (3)
C8A—C7A—C12A—C11A1.0 (3)C1C—C6C—C19C—O3C141.6 (17)
C8A—C7A—C3A—C2A33.0 (10)C2C—C1C—C6C—C5C61.9 (15)
C8A—C7A—C3A—C4A159.8 (12)C2C—C1C—C6C—C19C178.8 (13)
C8A—C7A—C3C—C2C8 (2)C2C—C3C—C4C—C5C28 (5)
C8A—C7A—C3C—C4C147 (2)C3C—C7A—C8A—C9A172.2 (10)
C8A—C9A—C10A—F1A180.0 (2)C3C—C7A—C12A—C11A171.9 (9)
C8A—C9A—C10A—C11A0.6 (4)C3C—C7A—C3A—C2A76 (5)
C9A—C10A—C11A—C12A1.4 (4)C3C—C7A—C3A—C4A91 (5)
C10A—C11A—C12A—C7A0.6 (3)C3C—C4C—C5C—O1C176 (3)
C12A—C7A—C8A—C9A1.9 (3)C3C—C4C—C5C—C6C6 (5)
C12A—C7A—C3A—C2A150.2 (6)C4C—C5C—C6C—C1C40 (3)
C12A—C7A—C3A—C4A17.0 (14)C4C—C5C—C6C—C19C161 (3)
C12A—C7A—C3C—C2C161.9 (14)C5C—C6C—C19C—O2C79 (3)
C12A—C7A—C3C—C4C42 (3)C5C—C6C—C19C—O3C98 (2)
C13A—C14A—C15A—C16A0.0C6C—C1C—C2C—C3C43.2 (18)
C13A—C1A—C2A—C3A159.9 (6)C19C—O3C—C20C—C21C174.3 (19)
C13A—C1A—C6A—C5A173.5 (7)C20C—O3C—C19C—O2C5 (4)
C13A—C1A—C6A—C19A61.8 (6)C20C—O3C—C19C—C6C172.2 (15)
C14A—C13A—C18A—C17A0.0Cl1C—C16C—C17C—C18C177.3 (19)
C14A—C13A—C1A—C2A104.5 (5)Cl1B—C16B—C17B—C18B178.78 (19)
C14A—C13A—C1A—C6A136.7 (4)F1B—C10B—C11B—C12B178.2 (2)
C14A—C15A—C16A—C17A0.0O1B—C5B—C6B—C1B152.6 (2)
C14A—C15A—C16A—Cl1A179.9 (8)O1B—C5B—C6B—C19B28.2 (3)
C15A—C16A—C17A—C18A0.0C1B—C2B—C3B—C4B26.2 (3)
C16A—C17A—C18A—C13A0.0C1B—C2B—C3B—C7B152.95 (18)
C18A—C13A—C14A—C15A0.0C1B—C6B—C19B—O2B120.3 (3)
C18A—C13A—C1A—C2A82.8 (8)C1B—C6B—C19B—O3B60.9 (2)
C18A—C13A—C1A—C6A35.9 (9)C1B—C13B—C14B—C15B180.0 (2)
C13C—C14C—C15C—C16C0.0C1B—C13B—C18B—C17B179.8 (2)
C13C—C1C—C2C—C3C146.2 (15)C2B—C1B—C6B—C5B51.7 (2)
C13C—C1C—C6C—C5C169.5 (13)C2B—C1B—C6B—C19B174.65 (17)
C13C—C1C—C6C—C19C71.2 (12)C2B—C1B—C13B—C14B94.2 (2)
C14C—C13C—C18C—C17C0.0C2B—C1B—C13B—C18B84.7 (2)
C14C—C13C—C1C—C2C35 (2)C2B—C3B—C4B—C5B2.4 (3)
C14C—C13C—C1C—C6C74 (2)C2B—C3B—C7B—C8B23.3 (3)
C14C—C15C—C16C—C17C0.0C2B—C3B—C7B—C12B153.8 (2)
C14C—C15C—C16C—Cl1C177.4 (18)C3B—C4B—C5B—O1B177.9 (2)
C15C—C16C—C17C—C18C0.0C3B—C4B—C5B—C6B4.3 (3)
C16C—C17C—C18C—C13C0.0C3B—C7B—C8B—C9B176.9 (2)
C18C—C13C—C14C—C15C0.0C3B—C7B—C12B—C11B177.1 (2)
C18C—C13C—C1C—C2C126.7 (11)C4B—C3B—C7B—C8B157.5 (2)
C18C—C13C—C1C—C6C123.5 (8)C4B—C3B—C7B—C12B25.4 (3)
O1A—C5A—C6A—C1A141.5 (14)C4B—C5B—C6B—C1B29.6 (3)
O1A—C5A—C6A—C19A12.7 (18)C4B—C5B—C6B—C19B154.0 (2)
C1A—C13A—C14A—C15A174.4 (6)C5B—C6B—C19B—O2B115.2 (3)
C1A—C13A—C18A—C17A171.6 (9)C5B—C6B—C19B—O3B63.6 (2)
C1A—C2A—C3A—C7A156.4 (6)C6B—C1B—C2B—C3B50.1 (2)
C1A—C2A—C3A—C4A10.8 (15)C6B—C1B—C13B—C14B141.6 (2)
C1A—C6A—C19A—O2A130.9 (11)C6B—C1B—C13B—C18B39.5 (3)
C1A—C6A—C19A—O3A48.1 (12)C7B—C3B—C4B—C5B176.66 (19)
C2A—C1A—C6A—C5A56.6 (7)C7B—C8B—C9B—C10B0.1 (4)
C2A—C1A—C6A—C19A178.6 (5)C8B—C7B—C12B—C11B0.1 (3)
C2A—C3A—C4A—C5A9 (3)C8B—C9B—C10B—F1B178.4 (2)
C3A—C7A—C8A—C9A174.9 (5)C8B—C9B—C10B—C11B0.6 (4)
C3A—C7A—C12A—C11A175.8 (5)C9B—C10B—C11B—C12B0.7 (4)
C3A—C7A—C3C—C2C86 (5)C10B—C11B—C12B—C7B0.4 (3)
C3A—C7A—C3C—C4C70 (5)C12B—C7B—C8B—C9B0.2 (3)
C3A—C4A—C5A—O1A174.7 (17)C13B—C1B—C2B—C3B175.38 (17)
C3A—C4A—C5A—C6A5 (3)C13B—C1B—C6B—C5B176.38 (17)
C4A—C5A—C6A—C1A38.6 (16)C13B—C1B—C6B—C19B60.7 (2)
C4A—C5A—C6A—C19A167.4 (13)C13B—C14B—C15B—C16B0.3 (4)
C5A—C6A—C19A—O2A103.6 (14)C14B—C13B—C18B—C17B1.3 (3)
C5A—C6A—C19A—O3A77.4 (12)C14B—C15B—C16B—Cl1B178.56 (18)
C6A—C1A—C2A—C3A43.6 (6)C14B—C15B—C16B—C17B1.5 (4)
C19A—O3A—C20A—C21A86.8 (10)C15B—C16B—C17B—C18B1.3 (4)
C20A—O3A—C19A—O2A4.0 (18)C16B—C17B—C18B—C13B0.1 (4)
C20A—O3A—C19A—C6A177.1 (7)C18B—C13B—C14B—C15B1.0 (3)
Cl1A—C16A—C17A—C18A179.9 (8)C19B—O3B—C20B—C21B107.9 (4)
O1C—C5C—C6C—C1C139 (3)C20B—O3B—C19B—O2B0.8 (4)
O1C—C5C—C6C—C19C17 (4)C20B—O3B—C19B—C6B179.6 (2)
C1C—C13C—C14C—C15C159 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8A—H8A···O1B0.952.553.478 (3)167
C2A—H2AA···O1B0.992.443.288 (6)143
C2A—H2AB···O2Bi0.992.563.432 (7)147
C2C—H2CA···O1B0.992.323.278 (18)164
C2C—H2CB···O2Bi0.992.423.40 (2)170
C2B—H2BA···O1Aii0.992.493.315 (8)140
C2B—H2BA···O1Cii0.992.563.380 (18)140
C2B—H2BB···O2Ciii0.992.583.436 (10)145
C8B—H8B···O1Aii0.952.503.379 (8)154
C8B—H8B···O1Cii0.952.543.417 (19)154
C9B—H9B···O2Aii0.952.543.274 (6)134
C14B—H14B···O2Aiii0.952.543.247 (5)131
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y, z+1; (iii) x+2, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8A—H8A···O1B0.952.553.478 (3)167.0
C2A—H2AA···O1B0.992.443.288 (6)143.2
C2A—H2AB···O2Bi0.992.563.432 (7)146.8
C2C—H2CA···O1B0.992.323.278 (18)163.7
C2C—H2CB···O2Bi0.992.423.40 (2)169.8
C2B—H2BA···O1Aii0.992.493.315 (8)140.2
C2B—H2BA···O1Cii0.992.563.380 (18)140.2
C2B—H2BB···O2Ciii0.992.583.436 (10)144.9
C8B—H8B···O1Aii0.952.503.379 (8)153.7
C8B—H8B···O1Cii0.952.543.417 (19)153.9
C9B—H9B···O2Aii0.952.543.274 (6)133.8
C14B—H14B···O2Aiii0.952.543.247 (5)131.1
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y, z+1; (iii) x+2, y+1, z+1.
 

Acknowledgements

BN thanks the UGC for financial assistance through a BSR one-time grant for the purchase of chemicals. MS thanks the DST for providing financial help for the research work through an INSPIRE Fellowship. RJB acknowledges the NSF–MRI program (grant No. CHE-0619278) for funds to purchase the X-ray diffractometer.

References

First citationAgilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, Oxfordshire, England.
First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.  CrossRef Web of Science
First citationAshalatha, B. V., Narayana, B. & Vijaya Raj, K. K. (2009). Phosphorus Sulfur Silicon, 184, 1904–1919.  Web of Science CrossRef CAS
First citationButcher, R. J., Akkurt, M., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2011). Acta Cryst. E67, o1346–o1347.  Web of Science CSD CrossRef CAS IUCr Journals
First citationCremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358.  CrossRef CAS Web of Science
First citationDutkiewicz, G., Narayana, B., Veena, K., Yathirajan, H. S. & Kubicki, M. (2011a). Acta Cryst. E67, o334–o335.  Web of Science CSD CrossRef CAS IUCr Journals
First citationDutkiewicz, G., Narayana, B., Veena, K., Yathirajan, H. S. & Kubicki, M. (2011b). Acta Cryst. E67, o336.  Web of Science CSD CrossRef IUCr Journals
First citationDutkiewicz, G., Narayana, B., Veena, K., Yathirajan, H. S. & Kubicki, M. (2011c). Acta Cryst. E67, o445–o446.  Web of Science CSD CrossRef CAS IUCr Journals
First citationFun, H.-K., Hemamalini, M., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2010). Acta Cryst. E66, o864–o865.  Web of Science CSD CrossRef CAS IUCr Journals
First citationHarrison, W. T. A., Mayekar, A. N., Yathirajan, H. S., Narayana, B. & Sarojini, B. K. (2010). Acta Cryst. E66, o2478.  Web of Science CSD CrossRef IUCr Journals
First citationKant, R., Gupta, V. K., Kapoor, K., Sapnakumari, M., Narayana, B. & Sarojini, B. K. (2012). Acta Cryst. E68, o2917–o2918.  CSD CrossRef CAS IUCr Journals
First citationPadmavathi, V., Reddy, B. J. M., Balaiah, A., Reddy, K. V. & Reddy, D. B. (2000). Molecules, 5, 1281–1286.  Web of Science CrossRef CAS
First citationSenguttuvan, S. & Nagarajan, S. (2010). Int. J. Chem. 2, 108–112.  CrossRef CAS
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationSreevidya, T. V., Narayana, B. & Yathirajan, H. S. (2010). Cent. Eur. J. Chem. 8, 171–181.  Web of Science CSD CrossRef

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 69| Part 12| December 2013| Pages o1839-o1840
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds