supplementary materials


lh5662 scheme

Acta Cryst. (2013). E69, o1839-o1840    [ doi:10.1107/S1600536813031851 ]

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

M. Sapnakumari, B. Narayana, H. S. Yathirajan, J. P. Jasinski and R. J. Butcher

Abstract top

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].

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 reflectionsθmax = 75.7°
Refinement top
R[F2 > 2σ(F2)] = 0.055H-atom parameters constrained
wR(F2) = 0.148Δρmax = 0.68 e Å3
S = 1.09Δρmin = 0.40 e Å3
7365 reflectionsAbsolute structure: ?
617 parametersAbsolute structure parameter: ?
177 restraintsRogers parameter: ?
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 top

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
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