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Acta Crystallogr Sect E Struct Rep Online. 2010 December 1; 66(Pt 12): o3229.
Published online 2010 November 20. doi:  10.1107/S1600536810046969
PMCID: PMC3011753

tert-Butyl 6-methyl-2-oxo-4-[4-(trifluoro­meth­oxy)anilino]cyclo­hex-3-ene-1-carboxyl­ate

Abstract

In the title compound, C19H22F3NO4, the dihedral angle between the benzene ring and the conjugated part of the enaminone ring is 42.5 (1)°. The ester substituent makes a dihedral angle of 81.3 (2)° with this latter moiety. The crystal structure is held together by strong N—H(...)O and weak C—H(...)O inter­molecular inter­actions. The enaminone ring is disordered over two orientations with relative occupancies of 0.794 (4) and 0.206 (4).

Related literature

The title compound posseses significant anti­convulsant properties. For the anti­convulsant properties of enamino­nes, see: Edafiogho et al. (1992 [triangle]); Eddington et al. (2003 [triangle]); Scott et al. (1993 [triangle], 1995 [triangle]).

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Object name is e-66-o3229-scheme1.jpg

Experimental

Crystal data

  • C19H22F3NO4
  • M r = 385.38
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o3229-efi1.jpg
  • a = 13.7896 (3) Å
  • b = 12.0820 (2) Å
  • c = 11.0023 (2) Å
  • β = 91.1978 (18)°
  • V = 1832.65 (6) Å3
  • Z = 4
  • Cu Kα radiation
  • μ = 1.01 mm−1
  • T = 123 K
  • 0.48 × 0.18 × 0.08 mm

Data collection

  • Oxford Diffraction Xcalibur Ruby Gemini diffractometer
  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007 [triangle]) T min = 0.852, T max = 1.000
  • 7085 measured reflections
  • 3607 independent reflections
  • 3095 reflections with I > 2σ(I)
  • R int = 0.018

Refinement

  • R[F 2 > 2σ(F 2)] = 0.058
  • wR(F 2) = 0.160
  • S = 1.06
  • 3607 reflections
  • 262 parameters
  • H-atom parameters constrained
  • Δρmax = 0.66 e Å−3
  • Δρmin = −0.39 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 [triangle]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810046969/hg2750sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810046969/hg2750Isup2.hkl

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

Acknowledgments

The authors are indebted to Mr James P. Stables, Epilepsy Branch, Division of Convulsive, Developmental and Neuromuscular Disorders, National Institute of Neurological Disorders and Stroke, for helpful discussions and initial data. The authors wish to acknowledge E. Jeannette Andrews, EdD, Deputy Director of the Center of Excellence at Howard University College of Pharmacy, Nursing and Allied Health Sciences, for her generous assistance in completing this project. RJB wishes to acknowledge the NSF–MRI program (grant CHE-0619278) for funds to purchase the diffractometer.

supplementary crystallographic information

Comment

Our research on enaminones has led to several compounds possessing anticonvulsant properties (Edafiogho et al., 1992; Eddington et al., 2003; Scott et al., 1993, 1995). The present work is part of a structural study of enaminones. Our group has extensively studied the effects of modification of the enaminone with substitutions at the methyl ester, ethyl ester, and without the ester group. We synthesized a series of carbo-tert-butoxy esters to evaluate the effect of added bulk and lipophilicity to the ester functionality. The title compound, tert-butyl-4-(4-trifluoromethoxyphenylamino)-6-methyl-2-oxocyclohex-3-en-1-oate (10) is highly active, with activity at <100 mg kg-1.

The compound was exclusively active in maximal electroshock seizure evaluation (MES) in mice, indicative of protection against tonic-clonic convulsions in humans (1/4 rats were protected at 15 min then 3/4 rats at 2 h and 4 hrs at post dose 50 mg kg-1 in rats, orally). The MES test with mice revealed no activity in the 30 minute study, however in the 4 h MES test 1/1 animals were protected at 30 mg kg-1, 3/3 animals protected at 100 mg kg-1, and 1/1 at 300 mg kg-1 with no toxicity. The scMET (subcutaneous phentylenetetrazole assessment), indicative of protection against absence seizures was 0/2 animals protected in doses of 62.5 to 500 mg kg-1. The compound displayed no toxicity from 62.5 to 500 mg kg-1 from 15 min to 24 h time range in all doses. A four hour MES test showed 4/16 mice protected at 100 mg kg-1 dose and maximium protection (7/8 mice protected) at 150 and 200 mg kg-1. In mice, a MES ED50 (median effective dose) of 121.87 mg kg-1 and TD50 (median toxic dose) of >500 mg kg-1, provided a protective index PI (defined as the ration of the median toxic dose to the median effective dose) at 95% confidence interval.

In view of the therapeutic interest in this compound its structure was determined. The conformation adopted by the molecule is such that the dihedral angle between the phenyl ring and conjugated part of the enaminone ring is 42.5 (1)°. The ester substituent makes a dihedral angle of 81.3 (2)° with this latter moiety. The crystal structure is held together by strong N—H···O and weak C—H···O intermolecular interactions. The enaminone ring is disordered over two conformations with relative occupancies of 0.794 (4)/0.206 (4).

Experimental

4-Carbo-t-butoxy-5-methylcyclohexane-1,3-dione (6.11 g, 27 mmol), mp 145–146°C (lit. mp 130–131.5°C), and 4-trifluoromethoxyaniline (4.428 ml g, 33 mmol) were added to a mixture of absolute EtOH (100 ml) and EtOAc (100 ml), and the solution was refluxed and stirred for 6 h with azeotropic removal of water by Dean-Stark trap. Evaporation under reduced pressure yielded a yellow solid which was recrystallized from 2-PrOH, 47% yield (mp 168–171°C). ).

Refinement

H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms with a C—H distances of 0.95 to 1.00 Å Uiso(H) = 1.2Ueq(C) and 0.98 Å for CH3 [Uiso(H) = 1.5Ueq(C)]. The H atoms attached to N were idealized with an N–H distance of 0.88 Å. The enaminone ring is disordered over two conformations with relative occupancies of 0.794 (4)/0.206 (4). Each component was constrained to have similar metrical and thermal parameters

Figures

Fig. 1.
Diagram of tert-butyl-4-(4-trifluoromethoxyphenylamino)-6-methyl-2-oxocyclohex-3-en-1-oate showing atom labeling scheme. Thermal ellipsoids drawn at the 30% probability level.
Fig. 2.
The molecular packing for tert-butyl-4-(4-trifluoromethoxyphenylamino)-6-methyl-2-oxocyclohex-3-en-1-oate viewed down the b axis. Intermolecular interactions are shown by dashed lines.

Crystal data

C19H22F3NO4F(000) = 808
Mr = 385.38Dx = 1.397 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybcCell parameters from 4437 reflections
a = 13.7896 (3) Åθ = 4.9–74.0°
b = 12.0820 (2) ŵ = 1.00 mm1
c = 11.0023 (2) ÅT = 123 K
β = 91.1978 (18)°Needle plate, colorless
V = 1832.65 (6) Å30.48 × 0.18 × 0.08 mm
Z = 4

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer3607 independent reflections
Radiation source: Enhance (Cu) X-ray Source3095 reflections with I > 2σ(I)
graphiteRint = 0.018
Detector resolution: 10.5081 pixels mm-1θmax = 74.1°, θmin = 4.9°
ω scansh = −16→14
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007)k = −14→8
Tmin = 0.852, Tmax = 1.000l = −13→13
7085 measured reflections

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)] = 0.058Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.160H-atom parameters constrained
S = 1.06w = 1/[σ2(Fo2) + (0.0769P)2 + 1.5676P] where P = (Fo2 + 2Fc2)/3
3607 reflections(Δ/σ)max < 0.001
262 parametersΔρmax = 0.66 e Å3
0 restraintsΔρmin = −0.38 e Å3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/UeqOcc. (<1)
F10.10734 (15)0.64674 (16)1.23883 (16)0.0709 (6)
F20.04027 (13)0.49236 (14)1.20234 (15)0.0589 (5)
F30.19525 (14)0.5113 (2)1.1945 (2)0.0850 (7)
O10.09751 (12)0.58259 (15)1.05175 (15)0.0420 (4)
O20.59047 (12)0.50627 (12)0.62115 (16)0.0397 (4)
O30.66640 (13)0.58950 (15)0.36210 (19)0.0490 (5)
O40.75913 (13)0.67009 (14)0.50910 (16)0.0437 (4)
N10.38563 (13)0.78606 (14)0.78117 (17)0.0301 (4)
H1A0.38440.85870.78700.036*
C10.31707 (15)0.72966 (17)0.85070 (19)0.0272 (4)
C20.28473 (16)0.78157 (17)0.95577 (19)0.0305 (5)
H2A0.31240.85030.98030.037*
C30.21290 (16)0.73416 (19)1.0246 (2)0.0336 (5)
H3A0.19060.77021.09550.040*
C40.17405 (15)0.63344 (18)0.9886 (2)0.0310 (5)
C50.20450 (16)0.58090 (18)0.8851 (2)0.0315 (5)
H5A0.17660.51210.86150.038*
C60.27590 (15)0.62856 (17)0.81557 (19)0.0295 (4)
H6A0.29690.59260.74400.035*
C70.11132 (18)0.5574 (2)1.1683 (2)0.0422 (6)
C80.45375 (14)0.74432 (16)0.70599 (18)0.0262 (4)
C9A0.5003 (12)0.8322 (14)0.6279 (13)0.0279 (12)0.794 (4)
H9AA0.51050.89950.67780.033*0.794 (4)
H9AB0.45460.85150.56060.033*0.794 (4)
C10A0.5972 (2)0.7986 (2)0.5737 (3)0.0267 (6)0.794 (4)
H10A0.64760.79490.64030.032*0.794 (4)
C11A0.58523 (18)0.6829 (2)0.5167 (2)0.0256 (5)0.794 (4)
H11A0.53100.68650.45500.031*0.794 (4)
C14A0.6263 (10)0.8853 (13)0.4833 (13)0.0344 (13)0.794 (4)
H14A0.68880.86510.44860.052*0.794 (4)
H14B0.63230.95710.52420.052*0.794 (4)
H14C0.57690.89010.41820.052*0.794 (4)
C9B0.505 (5)0.834 (6)0.641 (5)0.0279 (12)0.206 (4)
H9BA0.54940.87270.69770.033*0.206 (4)
H9BB0.45690.88780.60860.033*0.206 (4)
C10B0.5616 (9)0.7870 (10)0.5372 (11)0.0267 (6)0.206 (4)
H10B0.51480.75650.47520.032*0.206 (4)
C11B0.6240 (7)0.6924 (8)0.5856 (9)0.0256 (5)0.206 (4)
H11B0.67180.71330.65130.031*0.206 (4)
C14B0.630 (4)0.878 (5)0.471 (6)0.0344 (13)0.206 (4)
H14D0.63910.85720.38610.052*0.206 (4)
H14E0.69330.88180.51330.052*0.206 (4)
H14F0.59890.95130.47420.052*0.206 (4)
C120.55529 (16)0.60027 (17)0.6181 (2)0.0329 (5)
C130.48038 (15)0.63603 (16)0.69731 (19)0.0281 (4)
H13A0.44820.58260.74530.034*
C150.67459 (18)0.64028 (19)0.4539 (3)0.0421 (6)
C160.85219 (18)0.6464 (2)0.4484 (2)0.0421 (6)
C170.8520 (2)0.6974 (2)0.3218 (3)0.0543 (7)
H17A0.80620.65710.26870.081*
H17B0.91720.69270.28860.081*
H17C0.83230.77520.32670.081*
C180.9252 (3)0.7032 (3)0.5303 (4)0.0734 (10)
H18A0.92320.67060.61180.110*
H18B0.90990.78230.53500.110*
H18C0.99030.69370.49760.110*
C190.86786 (19)0.5226 (2)0.4465 (2)0.0435 (6)
H19A0.86130.49290.52880.065*
H19B0.93300.50650.41730.065*
H19C0.81950.48810.39210.065*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
F10.0923 (14)0.0713 (12)0.0501 (10)−0.0257 (10)0.0258 (9)−0.0172 (9)
F20.0668 (10)0.0592 (10)0.0515 (9)−0.0206 (8)0.0218 (8)0.0063 (8)
F30.0611 (11)0.1082 (17)0.0865 (14)0.0289 (11)0.0204 (10)0.0574 (13)
O10.0411 (9)0.0485 (10)0.0367 (9)−0.0135 (8)0.0053 (7)0.0018 (7)
O20.0395 (9)0.0199 (7)0.0601 (11)0.0059 (6)0.0104 (8)0.0037 (7)
O30.0455 (10)0.0339 (9)0.0674 (12)0.0013 (8)−0.0016 (9)−0.0065 (9)
O40.0535 (11)0.0357 (9)0.0425 (9)0.0030 (8)0.0121 (8)−0.0088 (7)
N10.0375 (10)0.0172 (8)0.0358 (9)0.0011 (7)0.0060 (7)−0.0013 (7)
C10.0280 (10)0.0223 (9)0.0315 (10)0.0030 (8)0.0007 (8)0.0014 (8)
C20.0344 (11)0.0230 (10)0.0342 (11)−0.0017 (8)−0.0001 (9)−0.0034 (8)
C30.0378 (12)0.0333 (11)0.0299 (10)−0.0012 (9)0.0034 (9)−0.0049 (9)
C40.0299 (10)0.0315 (11)0.0316 (10)−0.0039 (9)0.0019 (8)0.0039 (9)
C50.0331 (11)0.0240 (10)0.0372 (11)−0.0014 (8)−0.0021 (9)−0.0015 (8)
C60.0335 (11)0.0249 (10)0.0301 (10)0.0012 (8)0.0008 (8)−0.0031 (8)
C70.0416 (13)0.0422 (13)0.0432 (13)0.0024 (11)0.0114 (10)0.0049 (11)
C80.0269 (10)0.0222 (10)0.0295 (10)−0.0001 (8)−0.0014 (8)−0.0007 (8)
C9A0.0309 (19)0.0166 (10)0.036 (3)−0.0004 (13)0.0004 (19)0.000 (2)
C10A0.0268 (16)0.0212 (12)0.0321 (16)−0.0029 (11)−0.0003 (11)−0.0011 (11)
C11A0.0264 (13)0.0200 (11)0.0303 (13)−0.0010 (9)−0.0018 (9)−0.0006 (10)
C14A0.0413 (17)0.022 (2)0.040 (3)−0.0023 (16)0.009 (2)0.0008 (19)
C9B0.0309 (19)0.0166 (10)0.036 (3)−0.0004 (13)0.0004 (19)0.000 (2)
C10B0.0268 (16)0.0212 (12)0.0321 (16)−0.0029 (11)−0.0003 (11)−0.0011 (11)
C11B0.0264 (13)0.0200 (11)0.0303 (13)−0.0010 (9)−0.0018 (9)−0.0006 (10)
C14B0.0413 (17)0.022 (2)0.040 (3)−0.0023 (16)0.009 (2)0.0008 (19)
C120.0289 (10)0.0196 (10)0.0503 (13)−0.0002 (8)0.0050 (9)0.0015 (9)
C130.0313 (10)0.0191 (9)0.0340 (10)−0.0007 (8)0.0020 (8)0.0017 (8)
C150.0382 (13)0.0247 (11)0.0641 (17)0.0021 (9)0.0184 (11)0.0109 (11)
C160.0371 (13)0.0393 (13)0.0499 (14)0.0003 (10)0.0023 (10)−0.0053 (11)
C170.0510 (16)0.0486 (15)0.0641 (18)0.0055 (13)0.0220 (13)0.0111 (13)
C180.064 (2)0.0525 (18)0.102 (3)−0.0054 (16)−0.0229 (19)−0.0140 (18)
C190.0424 (13)0.0411 (13)0.0470 (14)0.0055 (11)0.0003 (10)−0.0025 (11)

Geometric parameters (Å, °)

F1—C71.331 (3)C11A—C121.559 (3)
F2—C71.316 (3)C11A—H11A1.0000
F3—C71.311 (3)C14A—H14A0.9800
O1—C71.328 (3)C14A—H14B0.9800
O1—C41.416 (3)C14A—H14C0.9800
O2—C121.235 (3)C9B—C10B1.50 (7)
O3—C151.185 (3)C9B—H9BA0.9900
O4—C151.352 (3)C9B—H9BB0.9900
O4—C161.487 (3)C10B—C11B1.520 (15)
N1—C81.361 (3)C10B—C14B1.63 (7)
N1—C11.405 (3)C10B—H10B1.0000
N1—H1A0.8800C11B—C121.510 (10)
C1—C21.396 (3)C11B—C151.740 (10)
C1—C61.398 (3)C11B—H11B1.0000
C2—C31.384 (3)C14B—H14D0.9800
C2—H2A0.9500C14B—H14E0.9800
C3—C41.384 (3)C14B—H14F0.9800
C3—H3A0.9500C12—C131.432 (3)
C4—C51.377 (3)C13—H13A0.9500
C5—C61.385 (3)C16—C181.503 (4)
C5—H5A0.9500C16—C191.512 (3)
C6—H6A0.9500C16—C171.523 (4)
C8—C131.363 (3)C17—H17A0.9800
C8—C9B1.48 (7)C17—H17B0.9800
C8—C9A1.516 (18)C17—H17C0.9800
C9A—C10A1.530 (17)C18—H18A0.9800
C9A—H9AA0.9900C18—H18B0.9800
C9A—H9AB0.9900C18—H18C0.9800
C10A—C14A1.504 (17)C19—H19A0.9800
C10A—C11A1.540 (4)C19—H19B0.9800
C10A—H10A1.0000C19—H19C0.9800
C11A—C151.515 (3)
C7—O1—C4118.68 (19)H9BA—C9B—H9BB108.1
C15—O4—C16119.42 (19)C9B—C10B—C11B108 (2)
C8—N1—C1129.19 (17)C9B—C10B—C14B113 (4)
C8—N1—H1A115.4C11B—C10B—C14B110 (2)
C1—N1—H1A115.4C9B—C10B—H10B108.4
C2—C1—C6119.10 (19)C11B—C10B—H10B108.4
C2—C1—N1117.59 (18)C14B—C10B—H10B108.4
C6—C1—N1123.18 (19)C12—C11B—C10B106.5 (8)
C3—C2—C1120.8 (2)C12—C11B—C15101.2 (6)
C3—C2—H2A119.6C10B—C11B—C15102.4 (8)
C1—C2—H2A119.6C12—C11B—H11B115.0
C2—C3—C4119.0 (2)C10B—C11B—H11B115.0
C2—C3—H3A120.5C15—C11B—H11B115.0
C4—C3—H3A120.5C10B—C14B—H14D109.5
C5—C4—C3121.3 (2)C10B—C14B—H14E109.5
C5—C4—O1116.67 (19)H14D—C14B—H14E109.5
C3—C4—O1122.0 (2)C10B—C14B—H14F109.5
C4—C5—C6119.9 (2)H14D—C14B—H14F109.5
C4—C5—H5A120.1H14E—C14B—H14F109.5
C6—C5—H5A120.1O2—C12—C13123.3 (2)
C5—C6—C1120.0 (2)O2—C12—C11B115.9 (4)
C5—C6—H6A120.0C13—C12—C11B112.7 (4)
C1—C6—H6A120.0O2—C12—C11A119.9 (2)
F3—C7—F2110.1 (2)C13—C12—C11A116.59 (18)
F3—C7—O1114.7 (2)C11B—C12—C11A35.1 (4)
F2—C7—O1108.6 (2)C8—C13—C12122.08 (19)
F3—C7—F1105.3 (3)C8—C13—H13A119.0
F2—C7—F1106.2 (2)C12—C13—H13A119.0
O1—C7—F1111.7 (2)O3—C15—O4125.9 (2)
N1—C8—C13126.06 (19)O3—C15—C11A120.0 (2)
N1—C8—C9B111 (2)O4—C15—C11A114.0 (2)
C13—C8—C9B122 (2)O3—C15—C11B149.8 (4)
N1—C8—C9A113.0 (6)O4—C15—C11B83.5 (4)
C13—C8—C9A121.0 (6)C11A—C15—C11B32.1 (3)
C9B—C8—C9A6(3)O4—C16—C18102.5 (2)
C8—C9A—C10A114.8 (10)O4—C16—C19108.8 (2)
C8—C9A—H9AA108.6C18—C16—C19111.5 (2)
C10A—C9A—H9AA108.6O4—C16—C17110.3 (2)
C8—C9A—H9AB108.6C18—C16—C17110.6 (3)
C10A—C9A—H9AB108.6C19—C16—C17112.6 (2)
H9AA—C9A—H9AB107.5C16—C17—H17A109.5
C14A—C10A—C9A108.7 (8)C16—C17—H17B109.5
C14A—C10A—C11A113.0 (5)H17A—C17—H17B109.5
C9A—C10A—C11A108.2 (7)C16—C17—H17C109.5
C14A—C10A—H10A108.9H17A—C17—H17C109.5
C9A—C10A—H10A108.9H17B—C17—H17C109.5
C11A—C10A—H10A108.9C16—C18—H18A109.5
C15—C11A—C10A114.4 (2)C16—C18—H18B109.5
C15—C11A—C12109.83 (19)H18A—C18—H18B109.5
C10A—C11A—C12108.5 (2)C16—C18—H18C109.5
C15—C11A—H11A108.0H18A—C18—H18C109.5
C10A—C11A—H11A108.0H18B—C18—H18C109.5
C12—C11A—H11A108.0C16—C19—H19A109.5
C8—C9B—C10B111 (4)C16—C19—H19B109.5
C8—C9B—H9BA109.5H19A—C19—H19B109.5
C10B—C9B—H9BA109.5C16—C19—H19C109.5
C8—C9B—H9BB109.5H19A—C19—H19C109.5
C10B—C9B—H9BB109.5H19B—C19—H19C109.5
C8—N1—C1—C2153.2 (2)C14B—C10B—C11B—C15−61 (2)
C8—N1—C1—C6−31.0 (3)C10B—C11B—C12—O2157.3 (6)
C6—C1—C2—C30.0 (3)C15—C11B—C12—O250.7 (6)
N1—C1—C2—C3176.0 (2)C10B—C11B—C12—C13−52.9 (8)
C1—C2—C3—C40.7 (3)C15—C11B—C12—C13−159.6 (3)
C2—C3—C4—C5−1.0 (3)C10B—C11B—C12—C11A51.5 (7)
C2—C3—C4—O1−177.2 (2)C15—C11B—C12—C11A−55.2 (5)
C7—O1—C4—C5123.9 (2)C15—C11A—C12—O2−14.0 (3)
C7—O1—C4—C3−59.7 (3)C10A—C11A—C12—O2−139.7 (2)
C3—C4—C5—C60.5 (3)C15—C11A—C12—C13171.5 (2)
O1—C4—C5—C6176.93 (19)C10A—C11A—C12—C1345.8 (3)
C4—C5—C6—C10.2 (3)C15—C11A—C12—C11B79.3 (7)
C2—C1—C6—C5−0.4 (3)C10A—C11A—C12—C11B−46.4 (7)
N1—C1—C6—C5−176.20 (19)N1—C8—C13—C12−177.9 (2)
C4—O1—C7—F3−44.1 (3)C9B—C8—C13—C12−4(3)
C4—O1—C7—F2−167.7 (2)C9A—C8—C13—C122.3 (7)
C4—O1—C7—F175.5 (3)O2—C12—C13—C8169.1 (2)
C1—N1—C8—C13−11.5 (4)C11B—C12—C13—C822.0 (5)
C1—N1—C8—C9B174 (2)C11A—C12—C13—C8−16.5 (3)
C1—N1—C8—C9A168.4 (6)C16—O4—C15—O34.9 (4)
N1—C8—C9A—C10A161.2 (6)C16—O4—C15—C11A−172.1 (2)
C13—C8—C9A—C10A−19.0 (11)C16—O4—C15—C11B177.6 (4)
C9B—C8—C9A—C10A85 (30)C10A—C11A—C15—O3−141.6 (2)
C8—C9A—C10A—C14A170.9 (8)C12—C11A—C15—O396.1 (3)
C8—C9A—C10A—C11A47.8 (9)C10A—C11A—C15—O435.6 (3)
C14A—C10A—C11A—C1556.9 (7)C12—C11A—C15—O4−86.7 (2)
C9A—C10A—C11A—C15177.4 (6)C10A—C11A—C15—C11B55.1 (6)
C14A—C10A—C11A—C12179.9 (6)C12—C11A—C15—C11B−67.2 (6)
C9A—C10A—C11A—C12−59.6 (6)C12—C11B—C15—O336.2 (11)
N1—C8—C9B—C10B−166 (2)C10B—C11B—C15—O3−73.7 (10)
C13—C8—C9B—C10B19 (4)C12—C11B—C15—O4−132.0 (5)
C9A—C8—C9B—C10B−60 (28)C10B—C11B—C15—O4118.2 (7)
C8—C9B—C10B—C11B−51 (4)C12—C11B—C15—C11A65.9 (6)
C8—C9B—C10B—C14B−173 (3)C10B—C11B—C15—C11A−44.0 (6)
C9B—C10B—C11B—C1269 (3)C15—O4—C16—C18173.6 (2)
C14B—C10B—C11B—C12−167 (2)C15—O4—C16—C19−68.2 (3)
C9B—C10B—C11B—C15174 (3)C15—O4—C16—C1755.8 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1A···O2i0.882.082.886 (2)153
C2—H2A···O2i0.952.583.333 (3)136
C6—H6A···O3ii0.952.553.385 (3)147
C9B—H9BA···O3iii0.992.443.40 (6)162

Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) −x+1, −y+1, −z+1; (iii) x, −y+3/2, z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG2750).

References

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  • Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED Oxford Diffraction Ltd, Abingdon, England.
  • Scott, K. R., Edafiogho, I. O., Richardson, E. R., Farrar, V. A., Moore, J. A., Tietz, E., Hinko, C. N., Chang, H., El-Assadi, A. & Nicholson, J. M. (1993). J. Med. Chem.36, 1947–1955. [PubMed]
  • Scott, K. R., Rankin, G. O., Stables, J. P., Alexander, M. S., Edafiogho, I. O., Farrar, V. A., Kolen, K. R., Moore, J. A., Sims, L. D. & Tonnu, A. D. (1995). J. Med. Chem.38, 4033–4043. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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