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Acta Crystallogr Sect E Struct Rep Online. 2012 June 1; 68(Pt 6): o1864–o1865.
Published online 2012 May 23. doi:  10.1107/S1600536812022210
PMCID: PMC3379430

Ethyl 1-phenyl-2-[4-(trifluoro­meth­yl)phen­yl]-1H-benzimidazole-5-carboxyl­ate

Abstract

The asymmetric unit of the title compound, C23H17F3N2O2, contains two mol­ecules. In one of the mol­ecules, the phenyl and triflouromethyl-substituted benzene rings form dihedral angles of 52.05 (8) and 33.70 (8)°, respectively, with the benzimidazole ring system, while the dihedral angle between them is 58.24 (10)°. The corresponding values in the other mol­ecule are 58.40 (8), 25.90 (8) and 60.83 (10)°, respectively. In the crystal, mol­ecules are linked into chains along [100] by C—H(...)O and C—H(...)N hydrogen bonds. Aromatic π–π stacking inter­actions [centroid–centroid distance = 3.6700 (12) Å] also occur.

Related literature  

For background to benzimidazole derivatives as drugs, see: Spasov et al. (1999 [triangle]); Grassmann et al. (2002 [triangle]); Demirayak et al. (2002 [triangle]); Evans et al. (1997 [triangle]). For related structures, see: Yoon et al. (2011 [triangle]); Kassim et al. (2012 [triangle]). For stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-68-o1864-scheme1.jpg

Experimental  

Crystal data  

  • C23H17F3N2O2
  • M r = 410.39
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-68-o1864-efi1.jpg
  • a = 9.8548 (2) Å
  • b = 25.0714 (6) Å
  • c = 16.0566 (4) Å
  • β = 107.023 (1)°
  • V = 3793.35 (15) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.11 mm−1
  • T = 100 K
  • 0.43 × 0.37 × 0.28 mm

Data collection  

  • Bruker SMART APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2009 [triangle]) T min = 0.953, T max = 0.969
  • 36855 measured reflections
  • 10921 independent reflections
  • 5999 reflections with I > 2σ(I)
  • R int = 0.052

Refinement  

  • R[F 2 > 2σ(F 2)] = 0.062
  • wR(F 2) = 0.142
  • S = 1.03
  • 10921 reflections
  • 543 parameters
  • H-atom parameters constrained
  • Δρmax = 0.30 e Å−3
  • Δρmin = −0.35 e Å−3

Data collection: APEX2 (Bruker, 2009 [triangle]); cell refinement: SAINT (Bruker, 2009 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812022210/hb6782sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812022210/hb6782Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812022210/hb6782Isup3.cml

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

Acknowledgments

The authors thank the Malaysian Government and Universiti Sains Malaysia (USM) for the Research University Grant Nos.1001/PFIZIK/811151 and 1001/PSK/8620012. The authors also wish to express their thanks to the Pharmacogenetic and Novel Therapeutic Research, Institute for Research in Mol­ecular Medicine, Universiti Sains Malaysia. SA also thanks the Malaysian government and USM for an Academic Staff Training Scheme (ASTS) fellowship.

supplementary crystallographic information

Comment

The benzimidazole nucleus is an important pharmacophore in drug discovery (Spasov et al., 1999). They thus generate a lot of pharmacological interests (Grassmann et al., 2002; Demirayak et al., 2002; Evans et al., 1997). As part of our studies in this area, the crystal structure determination of the title compound was carried out and the results are presented here.

The asymmetric unit of the title compound (Fig 1), consists of two crystallographically independent molecules A and B. The benzimidazole ring system in both molecules, N1A/N2A/C1A—C7A and N1B/N2B/C1B—C7B, are essentially planar with a maximum deviation of 0.014 (2) Å at atom C7A and of 0.006 (2) Å at atom N2B, respectively. In molecule A, the benzimidazole ring (N1A/N2A/C1A—C7A) makes dihedral angles of 52.05 (8) and 33.70 (8)°, respectively with the phenyl ring (C14A–C19A) and the triflouromethyl-substituted phenyl ring (C8A–C13A). The corresponding dihedral angles in molecule B are 58.40 (8) and 25.90 (8)°.

In addition, the phenyl ring and the triflouromethyl-substituted phenyl ring form dihedral angles of 58.24 (10) and 60.83 (10)° in molecule A and B, respectively. Bond lengths and angles are within normal ranges and are comparable to related structure (Yoon et al., 2011; Kassim et al., 2012).

In the crystal (Fig. 2), C22B—H22D···O2A, C17B—H17B···N1B and C22A—H22A···O2B (Table 1) hydrogen bonds link the molecules into one-dimensional chains along a-axis. π–π interactions of Cg1···Cg2 = 3.6700 (12) Å (symmetry code: 1 - x,1 - y,2 - z) further stabilized the structure [Cg1 and Cg2 are the centroids of the N1A/N2A/C1A/C7A/C8A and C1B–C6B rings, respectively].

Experimental

Ethyl 3-amino-4-(phenyl amino) benzoate (0.84 mmol) and sodium metabisulfite adduct of trifluoromethyl benzaldehyde (1.68 mmol) were dissolved in DMF. The reaction mixture was reflux at 130 °C for 2 h. After completion, the reaction mixture was diluted in ethyl acetate (20 ml) and washed with water (20 ml). The organic layer was collected, dried over Na2SO4 and the evaporated in vacuo to yield the product. The product was recrystallized from ethyl acetate as colourless blocks.

Refinement

All H atoms were positioned geometrically [C–H = 0.95–0.99 Å] and refined using a riding model with Uiso(H) = 1.2 and 1.5 Ueq(C). A rotating group model was applied to the methyl groups. In the final refinement, two outliers (0 2 0 and 0 0 2) were omitted.

Figures

Fig. 1.
The molecular structure of the title compound, showing 50% probability displacement ellipsoids.
Fig. 2.
The crystal packing of the title compound. The H atoms not involved in the intermolecular interactions (dashed lines) have been omitted for clarity.

Crystal data

C23H17F3N2O2F(000) = 1696
Mr = 410.39Dx = 1.437 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 7502 reflections
a = 9.8548 (2) Åθ = 2.2–29.0°
b = 25.0714 (6) ŵ = 0.11 mm1
c = 16.0566 (4) ÅT = 100 K
β = 107.023 (1)°Block, colourless
V = 3793.35 (15) Å30.43 × 0.37 × 0.28 mm
Z = 8

Data collection

Bruker SMART APEXII CCD diffractometer10921 independent reflections
Radiation source: fine-focus sealed tube5999 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.052
[var phi] and ω scansθmax = 30.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)h = −13→8
Tmin = 0.953, Tmax = 0.969k = −35→28
36855 measured reflectionsl = −17→22

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.062Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.142H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.0497P)2 + 1.1602P] where P = (Fo2 + 2Fc2)/3
10921 reflections(Δ/σ)max = 0.001
543 parametersΔρmax = 0.30 e Å3
0 restraintsΔρmin = −0.35 e Å3

Special details

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.
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
F1A0.76297 (13)1.01889 (5)0.89337 (9)0.0404 (4)
F2A0.55907 (13)1.00949 (5)0.79924 (8)0.0359 (3)
F3A0.57601 (14)1.01271 (5)0.93564 (9)0.0386 (3)
O1A1.05923 (15)0.55832 (5)0.88980 (10)0.0290 (4)
O2A0.89188 (16)0.50085 (6)0.90308 (10)0.0341 (4)
N1A0.82356 (17)0.74226 (6)0.88432 (11)0.0218 (4)
N2A0.59828 (16)0.72851 (6)0.88711 (11)0.0206 (4)
C1A0.6608 (2)0.67850 (8)0.89085 (13)0.0212 (4)
C2A0.6093 (2)0.62721 (8)0.89629 (13)0.0238 (5)
H2AA0.51480.62120.89760.029*
C3A0.7023 (2)0.58550 (8)0.89961 (13)0.0250 (5)
H3AA0.67110.55000.90410.030*
C4A0.8416 (2)0.59399 (8)0.89653 (14)0.0242 (5)
C5A0.8915 (2)0.64522 (8)0.89047 (13)0.0227 (5)
H5AA0.98560.65100.88820.027*
C6A0.7995 (2)0.68802 (8)0.88787 (13)0.0212 (4)
C7A0.7031 (2)0.76499 (8)0.88416 (13)0.0211 (4)
C8A0.6837 (2)0.82335 (8)0.88447 (13)0.0195 (4)
C9A0.7566 (2)0.85508 (8)0.84015 (14)0.0229 (5)
H9AA0.81670.83890.81070.028*
C10A0.7417 (2)0.91004 (8)0.83904 (14)0.0239 (5)
H10A0.79000.93140.80790.029*
C11A0.6559 (2)0.93399 (8)0.88337 (14)0.0218 (4)
C12A0.5862 (2)0.90302 (8)0.92964 (13)0.0240 (5)
H12A0.52960.91950.96120.029*
C13A0.5996 (2)0.84796 (8)0.92967 (13)0.0220 (5)
H13A0.55090.82680.96080.026*
C14A0.4494 (2)0.73733 (8)0.87188 (13)0.0198 (4)
C15A0.3736 (2)0.76759 (8)0.80114 (13)0.0226 (5)
H15A0.42030.78300.76300.027*
C16A0.2291 (2)0.77507 (8)0.78670 (14)0.0250 (5)
H16A0.17700.79610.73870.030*
C17A0.1603 (2)0.75224 (8)0.84142 (15)0.0265 (5)
H17A0.06130.75750.83120.032*
C18A0.2361 (2)0.72168 (8)0.91109 (14)0.0256 (5)
H18A0.18860.70550.94820.031*
C19A0.3810 (2)0.71448 (8)0.92729 (14)0.0234 (5)
H19A0.43300.69400.97600.028*
C20A0.9312 (2)0.54611 (8)0.89753 (14)0.0260 (5)
C21A1.1536 (2)0.51374 (8)0.89029 (16)0.0330 (6)
H21A1.11260.49030.83960.040*
H21B1.16790.49250.94410.040*
C22A1.2901 (3)0.53614 (10)0.8861 (2)0.0666 (10)
H22A1.35720.50710.88750.100*
H22B1.32870.55980.93600.100*
H22C1.27490.55640.83190.100*
C23A0.6388 (2)0.99321 (8)0.87871 (15)0.0263 (5)
F1B0.26113 (14)−0.10576 (5)0.84724 (12)0.0597 (5)
F2B0.09026 (16)−0.10489 (5)0.90442 (10)0.0471 (4)
F3B0.04605 (15)−0.09778 (5)0.76703 (9)0.0454 (4)
O1B0.53146 (16)0.35301 (6)0.86297 (12)0.0435 (5)
O2B0.36752 (18)0.41052 (6)0.87921 (12)0.0436 (4)
N1B0.29935 (17)0.16935 (6)0.85506 (11)0.0221 (4)
N2B0.08626 (16)0.18163 (6)0.87819 (11)0.0199 (4)
C1B0.1461 (2)0.23184 (8)0.88029 (13)0.0200 (4)
C2B0.0975 (2)0.28262 (8)0.89265 (13)0.0232 (5)
H2BA0.00800.28780.90260.028*
C3B0.1855 (2)0.32487 (8)0.88979 (13)0.0248 (5)
H3BA0.15620.36000.89820.030*
C4B0.3183 (2)0.31702 (8)0.87455 (13)0.0233 (5)
C5B0.3658 (2)0.26639 (8)0.86268 (13)0.0228 (5)
H5BA0.45560.26120.85320.027*
C6B0.2778 (2)0.22339 (8)0.86507 (13)0.0213 (4)
C7B0.1845 (2)0.14569 (8)0.86316 (13)0.0200 (4)
C8B0.1679 (2)0.08739 (8)0.86005 (13)0.0200 (4)
C9B0.2440 (2)0.05866 (8)0.81417 (14)0.0239 (5)
H9BA0.30290.07710.78620.029*
C10B0.2346 (2)0.00394 (8)0.80904 (14)0.0265 (5)
H10B0.2856−0.01520.77680.032*
C11B0.1506 (2)−0.02321 (8)0.85099 (14)0.0245 (5)
C12B0.0767 (2)0.00470 (8)0.89859 (14)0.0242 (5)
H12B0.0205−0.01390.92810.029*
C13B0.0855 (2)0.05993 (8)0.90287 (14)0.0228 (5)
H13B0.03480.07910.93530.027*
C14B−0.0593 (2)0.17171 (7)0.87440 (13)0.0199 (4)
C15B−0.1489 (2)0.14730 (8)0.80140 (14)0.0226 (5)
H15B−0.11460.13680.75440.027*
C16B−0.2889 (2)0.13850 (8)0.79805 (15)0.0257 (5)
H16B−0.35060.12130.74870.031*
C17B−0.3405 (2)0.15442 (8)0.86555 (15)0.0281 (5)
H17B−0.43700.14840.86260.034*
C18B−0.2501 (2)0.17911 (8)0.93713 (16)0.0303 (5)
H18B−0.28520.19040.98340.036*
C19B−0.1085 (2)0.18781 (8)0.94274 (14)0.0258 (5)
H19B−0.04660.20450.99260.031*
C20B0.4053 (2)0.36554 (9)0.87282 (14)0.0284 (5)
C21B0.6254 (3)0.39661 (10)0.8563 (2)0.0538 (8)
H21C0.60170.42910.88420.065*
H21D0.61460.40470.79430.065*
C22B0.7715 (3)0.37996 (10)0.90028 (18)0.0447 (7)
H22D0.83780.40620.88910.067*
H22E0.78920.34510.87810.067*
H22F0.78510.37750.96310.067*
C23B0.1376 (2)−0.08240 (9)0.84303 (16)0.0308 (5)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
F1A0.0245 (7)0.0212 (7)0.0727 (11)−0.0050 (5)0.0097 (7)−0.0006 (7)
F2A0.0357 (8)0.0293 (7)0.0399 (8)0.0048 (6)0.0065 (6)0.0090 (6)
F3A0.0476 (9)0.0257 (7)0.0482 (9)0.0051 (6)0.0230 (7)−0.0037 (6)
O1A0.0285 (8)0.0202 (7)0.0400 (10)0.0043 (6)0.0125 (7)0.0010 (7)
O2A0.0340 (9)0.0221 (8)0.0438 (10)−0.0001 (7)0.0073 (8)0.0012 (7)
N1A0.0199 (9)0.0203 (9)0.0249 (10)−0.0020 (7)0.0059 (7)−0.0009 (7)
N2A0.0154 (8)0.0194 (9)0.0263 (10)−0.0015 (7)0.0051 (7)0.0011 (7)
C1A0.0211 (11)0.0207 (10)0.0200 (11)−0.0026 (8)0.0031 (8)−0.0006 (9)
C2A0.0190 (11)0.0244 (11)0.0263 (12)−0.0040 (8)0.0039 (9)0.0015 (9)
C3A0.0252 (11)0.0204 (11)0.0257 (12)−0.0052 (9)0.0015 (9)0.0021 (9)
C4A0.0230 (11)0.0225 (11)0.0245 (12)0.0001 (9)0.0030 (9)0.0002 (9)
C5A0.0210 (11)0.0215 (11)0.0246 (12)−0.0020 (9)0.0049 (9)−0.0005 (9)
C6A0.0198 (10)0.0210 (10)0.0213 (12)−0.0036 (8)0.0038 (8)−0.0025 (9)
C7A0.0175 (10)0.0246 (11)0.0203 (11)−0.0035 (8)0.0043 (8)0.0001 (9)
C8A0.0154 (10)0.0219 (10)0.0202 (11)−0.0007 (8)0.0036 (8)−0.0023 (9)
C9A0.0185 (10)0.0257 (11)0.0252 (12)−0.0004 (8)0.0075 (9)−0.0009 (9)
C10A0.0229 (11)0.0223 (11)0.0271 (12)−0.0040 (9)0.0082 (9)0.0018 (9)
C11A0.0185 (10)0.0188 (10)0.0254 (12)−0.0016 (8)0.0020 (9)−0.0010 (9)
C12A0.0199 (11)0.0268 (11)0.0249 (12)−0.0002 (9)0.0062 (9)−0.0046 (9)
C13A0.0193 (11)0.0233 (11)0.0233 (12)−0.0042 (8)0.0058 (9)0.0005 (9)
C14A0.0158 (10)0.0197 (10)0.0227 (11)−0.0023 (8)0.0039 (8)−0.0036 (9)
C15A0.0244 (11)0.0205 (10)0.0227 (12)−0.0020 (8)0.0064 (9)−0.0021 (9)
C16A0.0224 (11)0.0200 (10)0.0293 (12)0.0022 (8)0.0023 (9)−0.0029 (9)
C17A0.0193 (11)0.0247 (11)0.0359 (14)−0.0019 (9)0.0084 (10)−0.0101 (10)
C18A0.0234 (11)0.0249 (11)0.0308 (13)−0.0076 (9)0.0116 (10)−0.0051 (10)
C19A0.0226 (11)0.0232 (11)0.0231 (12)−0.0051 (9)0.0050 (9)−0.0021 (9)
C20A0.0252 (12)0.0230 (12)0.0268 (13)−0.0010 (9)0.0027 (9)0.0011 (9)
C21A0.0357 (13)0.0208 (11)0.0447 (15)0.0066 (10)0.0154 (11)0.0002 (10)
C22A0.061 (2)0.0321 (15)0.128 (3)0.0102 (13)0.062 (2)0.0098 (17)
C23A0.0204 (11)0.0253 (11)0.0330 (14)0.0005 (9)0.0072 (10)−0.0014 (10)
F1B0.0283 (8)0.0248 (7)0.1254 (15)0.0052 (6)0.0214 (9)−0.0106 (8)
F2B0.0639 (10)0.0245 (7)0.0554 (10)−0.0010 (7)0.0214 (8)0.0070 (7)
F3B0.0501 (9)0.0302 (7)0.0482 (9)−0.0089 (6)0.0025 (7)−0.0122 (7)
O1B0.0266 (9)0.0250 (8)0.0791 (14)−0.0038 (7)0.0159 (9)0.0166 (9)
O2B0.0593 (12)0.0212 (9)0.0592 (12)−0.0064 (8)0.0310 (10)−0.0041 (8)
N1B0.0210 (9)0.0203 (9)0.0251 (10)0.0012 (7)0.0070 (8)0.0017 (7)
N2B0.0164 (8)0.0196 (9)0.0235 (10)0.0008 (7)0.0056 (7)−0.0013 (7)
C1B0.0182 (10)0.0203 (10)0.0197 (11)0.0001 (8)0.0030 (8)−0.0003 (9)
C2B0.0202 (11)0.0244 (11)0.0226 (12)0.0016 (9)0.0027 (9)−0.0007 (9)
C3B0.0293 (12)0.0185 (10)0.0231 (12)0.0021 (9)0.0021 (9)−0.0009 (9)
C4B0.0256 (11)0.0220 (11)0.0195 (11)−0.0035 (9)0.0023 (9)0.0016 (9)
C5B0.0209 (11)0.0240 (11)0.0233 (12)−0.0008 (9)0.0062 (9)0.0040 (9)
C6B0.0210 (11)0.0219 (11)0.0205 (11)0.0024 (8)0.0052 (9)0.0011 (9)
C7B0.0168 (10)0.0233 (11)0.0198 (11)0.0019 (8)0.0053 (8)0.0004 (9)
C8B0.0160 (10)0.0208 (10)0.0213 (11)0.0011 (8)0.0025 (8)−0.0009 (9)
C9B0.0204 (11)0.0254 (11)0.0270 (12)−0.0006 (9)0.0085 (9)−0.0021 (9)
C10B0.0212 (11)0.0276 (12)0.0320 (13)0.0026 (9)0.0099 (10)−0.0052 (10)
C11B0.0176 (10)0.0215 (11)0.0299 (13)0.0009 (8)0.0000 (9)−0.0009 (9)
C12B0.0197 (11)0.0225 (11)0.0310 (13)0.0007 (9)0.0081 (9)0.0031 (10)
C13B0.0203 (11)0.0218 (11)0.0275 (12)0.0019 (8)0.0089 (9)−0.0011 (9)
C14B0.0148 (10)0.0168 (10)0.0277 (12)0.0003 (8)0.0056 (9)0.0011 (9)
C15B0.0230 (11)0.0200 (10)0.0239 (12)0.0010 (8)0.0053 (9)0.0012 (9)
C16B0.0191 (11)0.0203 (11)0.0330 (13)0.0006 (8)0.0004 (9)0.0001 (9)
C17B0.0167 (10)0.0218 (11)0.0458 (15)0.0005 (9)0.0090 (10)−0.0009 (10)
C18B0.0268 (12)0.0275 (12)0.0415 (15)0.0017 (9)0.0176 (11)−0.0053 (11)
C19B0.0208 (11)0.0271 (11)0.0299 (13)−0.0008 (9)0.0081 (9)−0.0055 (10)
C20B0.0344 (13)0.0253 (12)0.0227 (12)−0.0038 (10)0.0040 (10)0.0037 (10)
C21B0.0387 (16)0.0342 (14)0.086 (2)−0.0119 (12)0.0140 (15)0.0244 (15)
C22B0.0409 (16)0.0299 (13)0.0648 (19)−0.0133 (11)0.0179 (14)−0.0055 (13)
C23B0.0233 (12)0.0237 (11)0.0446 (16)−0.0015 (9)0.0090 (11)−0.0025 (11)

Geometric parameters (Å, º)

F1A—C23A1.341 (2)F1B—C23B1.335 (2)
F2A—C23A1.351 (2)F2B—C23B1.333 (3)
F3A—C23A1.337 (2)F3B—C23B1.344 (3)
O1A—C20A1.339 (2)O1B—C20B1.336 (3)
O1A—C21A1.453 (2)O1B—C21B1.457 (3)
O2A—C20A1.211 (2)O2B—C20B1.201 (3)
N1A—C7A1.316 (2)N1B—C7B1.317 (2)
N1A—C6A1.385 (2)N1B—C6B1.388 (2)
N2A—C1A1.390 (2)N2B—C1B1.386 (2)
N2A—C7A1.391 (2)N2B—C7B1.394 (2)
N2A—C14A1.432 (2)N2B—C14B1.440 (2)
C1A—C2A1.394 (3)C1B—C2B1.395 (3)
C1A—C6A1.402 (3)C1B—C6B1.405 (3)
C2A—C3A1.381 (3)C2B—C3B1.378 (3)
C2A—H2AA0.9500C2B—H2BA0.9500
C3A—C4A1.404 (3)C3B—C4B1.414 (3)
C3A—H3AA0.9500C3B—H3BA0.9500
C4A—C5A1.389 (3)C4B—C5B1.385 (3)
C4A—C20A1.488 (3)C4B—C20B1.493 (3)
C5A—C6A1.397 (3)C5B—C6B1.392 (3)
C5A—H5AA0.9500C5B—H5BA0.9500
C7A—C8A1.476 (3)C7B—C8B1.470 (3)
C8A—C13A1.395 (3)C8B—C13B1.390 (3)
C8A—C9A1.399 (3)C8B—C9B1.396 (3)
C9A—C10A1.385 (3)C9B—C10B1.376 (3)
C9A—H9AA0.9500C9B—H9BA0.9500
C10A—C11A1.390 (3)C10B—C11B1.389 (3)
C10A—H10A0.9500C10B—H10B0.9500
C11A—C12A1.388 (3)C11B—C12B1.389 (3)
C11A—C23A1.494 (3)C11B—C23B1.492 (3)
C12A—C13A1.387 (3)C12B—C13B1.388 (3)
C12A—H12A0.9500C12B—H12B0.9500
C13A—H13A0.9500C13B—H13B0.9500
C14A—C19A1.388 (3)C14B—C19B1.383 (3)
C14A—C15A1.388 (3)C14B—C15B1.386 (3)
C15A—C16A1.387 (3)C15B—C16B1.382 (3)
C15A—H15A0.9500C15B—H15B0.9500
C16A—C17A1.381 (3)C16B—C17B1.384 (3)
C16A—H16A0.9500C16B—H16B0.9500
C17A—C18A1.381 (3)C17B—C18B1.378 (3)
C17A—H17A0.9500C17B—H17B0.9500
C18A—C19A1.386 (3)C18B—C19B1.388 (3)
C18A—H18A0.9500C18B—H18B0.9500
C19A—H19A0.9500C19B—H19B0.9500
C21A—C22A1.477 (3)C21B—C22B1.466 (4)
C21A—H21A0.9900C21B—H21C0.9900
C21A—H21B0.9900C21B—H21D0.9900
C22A—H22A0.9800C22B—H22D0.9800
C22A—H22B0.9800C22B—H22E0.9800
C22A—H22C0.9800C22B—H22F0.9800
C20A—O1A—C21A116.27 (16)C20B—O1B—C21B117.78 (18)
C7A—N1A—C6A105.06 (16)C7B—N1B—C6B105.23 (16)
C1A—N2A—C7A105.71 (15)C1B—N2B—C7B106.20 (15)
C1A—N2A—C14A124.42 (16)C1B—N2B—C14B124.70 (16)
C7A—N2A—C14A128.78 (16)C7B—N2B—C14B127.95 (16)
N2A—C1A—C2A132.04 (18)N2B—C1B—C2B132.15 (18)
N2A—C1A—C6A105.60 (16)N2B—C1B—C6B105.46 (16)
C2A—C1A—C6A122.36 (18)C2B—C1B—C6B122.38 (18)
C3A—C2A—C1A116.82 (19)C3B—C2B—C1B116.82 (19)
C3A—C2A—H2AA121.6C3B—C2B—H2BA121.6
C1A—C2A—H2AA121.6C1B—C2B—H2BA121.6
C2A—C3A—C4A121.89 (19)C2B—C3B—C4B121.48 (19)
C2A—C3A—H3AA119.1C2B—C3B—H3BA119.3
C4A—C3A—H3AA119.1C4B—C3B—H3BA119.3
C5A—C4A—C3A120.80 (19)C5B—C4B—C3B121.23 (18)
C5A—C4A—C20A121.74 (19)C5B—C4B—C20B121.66 (19)
C3A—C4A—C20A117.43 (18)C3B—C4B—C20B117.10 (19)
C4A—C5A—C6A118.21 (19)C4B—C5B—C6B117.87 (19)
C4A—C5A—H5AA120.9C4B—C5B—H5BA121.1
C6A—C5A—H5AA120.9C6B—C5B—H5BA121.1
N1A—C6A—C5A129.64 (18)N1B—C6B—C5B129.42 (18)
N1A—C6A—C1A110.44 (17)N1B—C6B—C1B110.38 (17)
C5A—C6A—C1A119.91 (18)C5B—C6B—C1B120.20 (18)
N1A—C7A—N2A113.17 (17)N1B—C7B—N2B112.72 (17)
N1A—C7A—C8A123.14 (17)N1B—C7B—C8B122.31 (17)
N2A—C7A—C8A123.64 (17)N2B—C7B—C8B124.91 (17)
C13A—C8A—C9A119.04 (18)C13B—C8B—C9B119.18 (18)
C13A—C8A—C7A122.50 (18)C13B—C8B—C7B123.42 (18)
C9A—C8A—C7A118.43 (17)C9B—C8B—C7B117.35 (18)
C10A—C9A—C8A120.25 (19)C10B—C9B—C8B120.60 (19)
C10A—C9A—H9AA119.9C10B—C9B—H9BA119.7
C8A—C9A—H9AA119.9C8B—C9B—H9BA119.7
C9A—C10A—C11A120.08 (19)C9B—C10B—C11B119.93 (19)
C9A—C10A—H10A120.0C9B—C10B—H10B120.0
C11A—C10A—H10A120.0C11B—C10B—H10B120.0
C12A—C11A—C10A120.19 (18)C10B—C11B—C12B120.19 (19)
C12A—C11A—C23A121.10 (19)C10B—C11B—C23B119.67 (19)
C10A—C11A—C23A118.71 (18)C12B—C11B—C23B120.13 (19)
C13A—C12A—C11A119.70 (19)C13B—C12B—C11B119.65 (19)
C13A—C12A—H12A120.2C13B—C12B—H12B120.2
C11A—C12A—H12A120.2C11B—C12B—H12B120.2
C12A—C13A—C8A120.71 (19)C12B—C13B—C8B120.42 (19)
C12A—C13A—H13A119.6C12B—C13B—H13B119.8
C8A—C13A—H13A119.6C8B—C13B—H13B119.8
C19A—C14A—C15A120.24 (18)C19B—C14B—C15B121.01 (19)
C19A—C14A—N2A119.52 (18)C19B—C14B—N2B119.50 (18)
C15A—C14A—N2A120.22 (18)C15B—C14B—N2B119.47 (18)
C16A—C15A—C14A119.41 (19)C16B—C15B—C14B119.0 (2)
C16A—C15A—H15A120.3C16B—C15B—H15B120.5
C14A—C15A—H15A120.3C14B—C15B—H15B120.5
C17A—C16A—C15A120.6 (2)C15B—C16B—C17B121.0 (2)
C17A—C16A—H16A119.7C15B—C16B—H16B119.5
C15A—C16A—H16A119.7C17B—C16B—H16B119.5
C18A—C17A—C16A119.7 (2)C18B—C17B—C16B119.1 (2)
C18A—C17A—H17A120.2C18B—C17B—H17B120.4
C16A—C17A—H17A120.2C16B—C17B—H17B120.4
C17A—C18A—C19A120.5 (2)C17B—C18B—C19B121.1 (2)
C17A—C18A—H18A119.7C17B—C18B—H18B119.4
C19A—C18A—H18A119.7C19B—C18B—H18B119.4
C18A—C19A—C14A119.6 (2)C14B—C19B—C18B118.8 (2)
C18A—C19A—H19A120.2C14B—C19B—H19B120.6
C14A—C19A—H19A120.2C18B—C19B—H19B120.6
O2A—C20A—O1A123.51 (19)O2B—C20B—O1B123.6 (2)
O2A—C20A—C4A123.71 (19)O2B—C20B—C4B124.7 (2)
O1A—C20A—C4A112.77 (17)O1B—C20B—C4B111.72 (18)
O1A—C21A—C22A107.29 (18)O1B—C21B—C22B107.8 (2)
O1A—C21A—H21A110.3O1B—C21B—H21C110.1
C22A—C21A—H21A110.3C22B—C21B—H21C110.1
O1A—C21A—H21B110.3O1B—C21B—H21D110.1
C22A—C21A—H21B110.3C22B—C21B—H21D110.1
H21A—C21A—H21B108.5H21C—C21B—H21D108.5
C21A—C22A—H22A109.5C21B—C22B—H22D109.5
C21A—C22A—H22B109.5C21B—C22B—H22E109.5
H22A—C22A—H22B109.5H22D—C22B—H22E109.5
C21A—C22A—H22C109.5C21B—C22B—H22F109.5
H22A—C22A—H22C109.5H22D—C22B—H22F109.5
H22B—C22A—H22C109.5H22E—C22B—H22F109.5
F3A—C23A—F1A106.59 (17)F2B—C23B—F1B106.76 (19)
F3A—C23A—F2A106.13 (16)F2B—C23B—F3B105.26 (17)
F1A—C23A—F2A105.61 (17)F1B—C23B—F3B106.24 (18)
F3A—C23A—C11A113.40 (18)F2B—C23B—C11B113.44 (19)
F1A—C23A—C11A112.59 (17)F1B—C23B—C11B112.17 (17)
F2A—C23A—C11A111.94 (17)F3B—C23B—C11B112.42 (18)
C7A—N2A—C1A—C2A178.8 (2)C7B—N2B—C1B—C2B179.8 (2)
C14A—N2A—C1A—C2A−12.3 (3)C14B—N2B—C1B—C2B11.3 (3)
C7A—N2A—C1A—C6A−1.3 (2)C7B—N2B—C1B—C6B0.8 (2)
C14A—N2A—C1A—C6A167.61 (18)C14B—N2B—C1B—C6B−167.79 (18)
N2A—C1A—C2A—C3A−179.5 (2)N2B—C1B—C2B—C3B−179.3 (2)
C6A—C1A—C2A—C3A0.7 (3)C6B—C1B—C2B—C3B−0.3 (3)
C1A—C2A—C3A—C4A−0.8 (3)C1B—C2B—C3B—C4B0.3 (3)
C2A—C3A—C4A—C5A0.4 (3)C2B—C3B—C4B—C5B−0.6 (3)
C2A—C3A—C4A—C20A−177.97 (19)C2B—C3B—C4B—C20B−179.96 (19)
C3A—C4A—C5A—C6A0.2 (3)C3B—C4B—C5B—C6B0.8 (3)
C20A—C4A—C5A—C6A178.52 (19)C20B—C4B—C5B—C6B−179.85 (19)
C7A—N1A—C6A—C5A−179.2 (2)C7B—N1B—C6B—C5B179.8 (2)
C7A—N1A—C6A—C1A−0.7 (2)C7B—N1B—C6B—C1B0.5 (2)
C4A—C5A—C6A—N1A178.1 (2)C4B—C5B—C6B—N1B179.9 (2)
C4A—C5A—C6A—C1A−0.4 (3)C4B—C5B—C6B—C1B−0.8 (3)
N2A—C1A—C6A—N1A1.3 (2)N2B—C1B—C6B—N1B−0.8 (2)
C2A—C1A—C6A—N1A−178.83 (18)C2B—C1B—C6B—N1B−179.96 (18)
N2A—C1A—C6A—C5A−179.99 (18)N2B—C1B—C6B—C5B179.78 (18)
C2A—C1A—C6A—C5A−0.1 (3)C2B—C1B—C6B—C5B0.6 (3)
C6A—N1A—C7A—N2A−0.2 (2)C6B—N1B—C7B—N2B0.0 (2)
C6A—N1A—C7A—C8A177.40 (18)C6B—N1B—C7B—C8B−177.55 (18)
C1A—N2A—C7A—N1A1.0 (2)C1B—N2B—C7B—N1B−0.5 (2)
C14A—N2A—C7A—N1A−167.28 (18)C14B—N2B—C7B—N1B167.55 (18)
C1A—N2A—C7A—C8A−176.60 (18)C1B—N2B—C7B—C8B176.97 (18)
C14A—N2A—C7A—C8A15.1 (3)C14B—N2B—C7B—C8B−15.0 (3)
N1A—C7A—C8A—C13A−143.8 (2)N1B—C7B—C8B—C13B151.6 (2)
N2A—C7A—C8A—C13A33.6 (3)N2B—C7B—C8B—C13B−25.7 (3)
N1A—C7A—C8A—C9A34.0 (3)N1B—C7B—C8B—C9B−25.9 (3)
N2A—C7A—C8A—C9A−148.65 (19)N2B—C7B—C8B—C9B156.83 (19)
C13A—C8A—C9A—C10A−2.0 (3)C13B—C8B—C9B—C10B1.9 (3)
C7A—C8A—C9A—C10A−179.83 (18)C7B—C8B—C9B—C10B179.48 (19)
C8A—C9A—C10A—C11A1.2 (3)C8B—C9B—C10B—C11B−1.1 (3)
C9A—C10A—C11A—C12A0.7 (3)C9B—C10B—C11B—C12B−0.4 (3)
C9A—C10A—C11A—C23A−178.25 (19)C9B—C10B—C11B—C23B178.2 (2)
C10A—C11A—C12A—C13A−1.6 (3)C10B—C11B—C12B—C13B1.0 (3)
C23A—C11A—C12A—C13A177.27 (19)C23B—C11B—C12B—C13B−177.6 (2)
C11A—C12A—C13A—C8A0.7 (3)C11B—C12B—C13B—C8B−0.2 (3)
C9A—C8A—C13A—C12A1.1 (3)C9B—C8B—C13B—C12B−1.3 (3)
C7A—C8A—C13A—C12A178.79 (18)C7B—C8B—C13B—C12B−178.71 (19)
C1A—N2A—C14A—C19A57.5 (3)C1B—N2B—C14B—C19B−63.5 (3)
C7A—N2A—C14A—C19A−136.2 (2)C7B—N2B—C14B—C19B130.5 (2)
C1A—N2A—C14A—C15A−121.2 (2)C1B—N2B—C14B—C15B115.0 (2)
C7A—N2A—C14A—C15A45.1 (3)C7B—N2B—C14B—C15B−51.0 (3)
C19A—C14A—C15A—C16A0.4 (3)C19B—C14B—C15B—C16B−0.8 (3)
N2A—C14A—C15A—C16A179.07 (17)N2B—C14B—C15B—C16B−179.30 (17)
C14A—C15A—C16A—C17A−0.7 (3)C14B—C15B—C16B—C17B1.0 (3)
C15A—C16A—C17A—C18A0.0 (3)C15B—C16B—C17B—C18B−0.4 (3)
C16A—C17A—C18A—C19A1.1 (3)C16B—C17B—C18B—C19B−0.5 (3)
C17A—C18A—C19A—C14A−1.3 (3)C15B—C14B—C19B—C18B0.0 (3)
C15A—C14A—C19A—C18A0.6 (3)N2B—C14B—C19B—C18B178.46 (18)
N2A—C14A—C19A—C18A−178.09 (17)C17B—C18B—C19B—C14B0.7 (3)
C21A—O1A—C20A—O2A−1.4 (3)C21B—O1B—C20B—O2B−2.5 (3)
C21A—O1A—C20A—C4A179.94 (18)C21B—O1B—C20B—C4B177.3 (2)
C5A—C4A—C20A—O2A179.7 (2)C5B—C4B—C20B—O2B176.9 (2)
C3A—C4A—C20A—O2A−2.0 (3)C3B—C4B—C20B—O2B−3.8 (3)
C5A—C4A—C20A—O1A−1.6 (3)C5B—C4B—C20B—O1B−2.9 (3)
C3A—C4A—C20A—O1A176.72 (18)C3B—C4B—C20B—O1B176.40 (18)
C20A—O1A—C21A—C22A−176.9 (2)C20B—O1B—C21B—C22B144.2 (2)
C12A—C11A—C23A—F3A12.5 (3)C10B—C11B—C23B—F2B161.60 (19)
C10A—C11A—C23A—F3A−168.60 (18)C12B—C11B—C23B—F2B−19.8 (3)
C12A—C11A—C23A—F1A133.6 (2)C10B—C11B—C23B—F1B40.5 (3)
C10A—C11A—C23A—F1A−47.5 (3)C12B—C11B—C23B—F1B−140.8 (2)
C12A—C11A—C23A—F2A−107.6 (2)C10B—C11B—C23B—F3B−79.1 (2)
C10A—C11A—C23A—F2A71.4 (2)C12B—C11B—C23B—F3B99.5 (2)

Hydrogen-bond geometry (Å, º)

D—H···AD—HH···AD···AD—H···A
C22B—H22D···O2A0.982.433.250 (3)141
C17B—H17B···N1Bi0.952.623.524 (3)159
C22A—H22A···O2Bii0.982.433.250 (3)141

Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB6782).

References

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