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Acta Crystallogr Sect E Struct Rep Online. 2008 November 1; 64(Pt 11): o2227.
Published online 2008 October 31. doi:  10.1107/S160053680803376X
PMCID: PMC2959698

1,1-Bis(4-fluoro­phen­yl)-3,4-dihydro-1H-1,3-oxazino[3,4-a]indole

Abstract

The title compound, C23H17F2NO, which crystallizes with two independent mol­ecules in the asymmetric unit, was prepared by the cyclization of 4-[2-bis­(4-fluoro­phen­yl)methyl­eneamino]but-3-yn-1-ol at room temperature. The mol­ecules display a tripod conformation. The two fluoro­phenyl rings make dihedral angles of 79.26 (2) and 85.87 (1)° [86.53 (1) and 83.67 (2)° in the second mol­ecule] with the indole ring, and the dihedral angles between the fluoro­phenyl rings are 67.74 (2) and 66.33 (2)°, respectively. Furthermore, the indole rings are located on the edge of the respective oxazine half-chair ring systems. Nonconventional C—H(...)π contacts between indole and fluoro­phenyl rings are observed.

Related literature

For bond-length and angle data, see: Lee et al. (2000 [triangle]). For the synthesis of palladium-catalysed key inter­mediates to condensed heteroaromatic rings, see: Sakamoto et al. (1988 [triangle]). For the biological function of tryptamines and their derivatives, see: Monckton & McCormick (2002 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o2227-scheme1.jpg

Experimental

Crystal data

  • C23H17F2NO
  • M r = 361.38
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o2227-efi1.jpg
  • a = 10.9845 (11) Å
  • b = 11.2002 (11) Å
  • c = 15.1964 (16) Å
  • α = 87.6150 (10)°
  • β = 80.7510 (10)°
  • γ = 76.9900 (10)°
  • V = 1797.9 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 291 (2) K
  • 0.38 × 0.30 × 0.20 mm

Data collection

  • Bruker APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.965, T max = 0.981
  • 13827 measured reflections
  • 6630 independent reflections
  • 4487 reflections with I > 2σ(I)
  • R int = 0.019

Refinement

  • R[F 2 > 2σ(F 2)] = 0.039
  • wR(F 2) = 0.106
  • S = 1.02
  • 6630 reflections
  • 487 parameters
  • H-atom parameters constrained
  • Δρmax = 0.13 e Å−3
  • Δρmin = −0.16 e Å−3

Data collection: APEX2 (Bruker, 2004 [triangle]); cell refinement: SAINT (Bruker, 2004 [triangle]); data reduction: SAINT; 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 and PLATON (Spek, 2003 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680803376X/si2115sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680803376X/si2115Isup2.hkl

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

Acknowledgments

This work was supported by the Doctor Foundation of Luoyang Normal University.

supplementary crystallographic information

Comment

Indoles are one of the most widely distributed heterocyclic compounds in nature (Sakamoto et al., 1988). The indole ring appeares in tryptophan, an essential amino acid, and metabolites of tryptophan are important in the biological chemistry of both plants and animals (Monckton & McCormick, 2002). The potent physiological properties of these indole derivatives led to vast research of their use as medicines in the field of pharmaceutical chemistry. So in the recent decades, many chemists have been attracted by the synthesis of indoles. In this context, we report the synthesis of the title compound.

The asymmetric unit of the title compound contains two independent molecules (Fig. 1.), in both of which the bond lengths and angles are within ranges as reported by Lee et al. (2000). The structural analysis reveals that a surprizing feature is the lack of C—H···F interactions, but three weak non-conventional intermolecular C—H···π contacts with two fluorophenyl rings (F1, F4) and one indole ring are donors, whereas the indole rings (C3 - C8 and C26 - C31) and a fluorophenyl ring (C18 - C23) are π acceptors. Cg3, Cg5 and Cg11 are the centroids of the acceptor rings, for the intramolecular C—H···π contact, Cg9 is the centroid of the five-membered ring (N2, C24, C25, C26, C31). Details are given in Table 1. Furthermore, pseudosymmetry between the independent molecules can be described as an approximate twofold screw axis when viewed down the a axis.

Experimental

To a solution of 4-(2-bis(4-fluoridophenyl)methyleneamino)phenyl)but-3-yn-1-ol (0.5 mmol) in dry CH2Cl2 was added AuCl3 (5 mg). The mixture was stirred for 1 h at room temperature. After evaporation of the solvent, the residue was purified by column chromatography on silica gel(petroleum ether) to afford the title compound as a colorless solid (163 mg, yield 90%). The title compound was recrystallized from petroleum ether at room temperature to give the desired crystals suitable for single-crystal X-ray diffraction.

Refinement

All H atoms were positioned geometrically and treated as riding, with C—H bond lengths constrained to 0.93 Å (aromatic CH) or 0.97 Å (methylene CH2), and with Uĩso~(H) = 1.2Ueq(C) or 1.5Ueq(methylene C).

Figures

Fig. 1.
View of the molecular structure of (I) with atom numbering scheme and 30% probability displacement ellipsoids for non-hydrogen atoms.

Crystal data

C23H17F2NOZ = 4
Mr = 361.38F(000) = 752
Triclinic, P1Dx = 1.335 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.9845 (11) ÅCell parameters from 3583 reflections
b = 11.2002 (11) Åθ = 2.3–23.5°
c = 15.1964 (16) ŵ = 0.10 mm1
α = 87.615 (1)°T = 291 K
β = 80.751 (1)°Block, yellow
γ = 76.990 (1)°0.38 × 0.30 × 0.20 mm
V = 1797.9 (3) Å3

Data collection

Bruker APEXII CCD diffractometer6630 independent reflections
Radiation source: fine-focus sealed tube4487 reflections with I > 2σ(I)
graphiteRint = 0.019
[var phi] and ω scansθmax = 25.5°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −13→13
Tmin = 0.965, Tmax = 0.981k = −13→12
13827 measured reflectionsl = −18→18

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)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106H-atom parameters constrained
S = 1.02w = 1/[σ2(Fo2) + (0.0461P)2 + 0.2061P] where P = (Fo2 + 2Fc2)/3
6630 reflections(Δ/σ)max < 0.001
487 parametersΔρmax = 0.13 e Å3
0 restraintsΔρmin = −0.16 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*/Ueq
F10.15332 (10)0.20474 (12)0.53431 (8)0.0843 (4)
F20.62785 (13)0.67584 (11)0.14682 (8)0.0878 (4)
F30.30250 (12)−0.18113 (10)0.34221 (7)0.0807 (4)
F4−0.23605 (11)0.27910 (12)−0.03884 (8)0.0839 (4)
O10.66525 (11)0.33741 (11)0.48340 (7)0.0549 (3)
O20.31522 (11)0.17610 (11)0.01727 (7)0.0549 (3)
N10.72344 (12)0.18387 (13)0.37478 (9)0.0466 (3)
N20.24016 (12)0.32408 (12)0.12899 (9)0.0451 (3)
C10.84755 (16)0.15765 (18)0.39117 (12)0.0581 (5)
C20.91322 (18)0.05810 (19)0.34339 (14)0.0707 (6)
H20.99810.02170.34330.085*
C30.83131 (16)0.01843 (16)0.29349 (12)0.0549 (5)
C40.8460 (2)−0.07701 (18)0.23367 (15)0.0727 (6)
H40.9241−0.13110.21960.087*
C50.7454 (2)−0.09050 (19)0.19602 (14)0.0744 (6)
H50.7551−0.15400.15610.089*
C60.6289 (2)−0.01063 (18)0.21662 (13)0.0661 (5)
H60.5613−0.02220.19060.079*
C70.61015 (17)0.08564 (16)0.27459 (12)0.0543 (5)
H70.53190.13970.28720.065*
C80.71239 (15)0.09884 (15)0.31342 (11)0.0447 (4)
C90.8840 (2)0.2312 (2)0.45833 (15)0.0774 (6)
H9A0.96830.24420.43760.093*
H9B0.88580.18600.51410.093*
C100.79304 (19)0.3529 (2)0.47394 (13)0.0694 (6)
H10A0.80570.38960.52750.083*
H10B0.80850.40740.42420.083*
C110.63226 (15)0.29876 (15)0.40412 (10)0.0436 (4)
C120.50071 (15)0.27351 (15)0.43494 (10)0.0418 (4)
C130.48805 (17)0.18616 (16)0.50129 (11)0.0511 (4)
H130.55960.14250.52320.061*
C140.37155 (18)0.16283 (17)0.53536 (12)0.0569 (5)
H140.36370.10420.57980.068*
C150.26817 (17)0.22808 (17)0.50214 (12)0.0542 (5)
C160.27549 (17)0.31452 (17)0.43676 (12)0.0554 (5)
H160.20330.35740.41530.066*
C170.39377 (16)0.33680 (16)0.40305 (11)0.0498 (4)
H170.40080.39530.35830.060*
C180.63506 (15)0.39877 (15)0.33247 (10)0.0425 (4)
C190.57976 (17)0.51909 (17)0.35633 (12)0.0564 (5)
H190.54320.53700.41520.068*
C200.57780 (18)0.61303 (17)0.29443 (13)0.0595 (5)
H200.54070.69370.31090.071*
C210.63185 (18)0.58419 (18)0.20835 (12)0.0568 (5)
C220.68926 (18)0.46804 (17)0.18220 (12)0.0569 (5)
H220.72670.45150.12330.068*
C230.69101 (16)0.37452 (16)0.24493 (11)0.0488 (4)
H230.73030.29450.22800.059*
C240.35721 (16)0.35631 (18)0.11829 (12)0.0542 (5)
C250.34808 (19)0.45452 (19)0.16917 (13)0.0644 (5)
H250.41320.49350.17360.077*
C260.22186 (17)0.48855 (16)0.21507 (11)0.0513 (4)
C270.1581 (2)0.58283 (18)0.27414 (13)0.0673 (6)
H270.20070.63820.29210.081*
C280.0323 (2)0.59277 (19)0.30526 (13)0.0721 (6)
H28−0.01090.65580.34400.087*
C29−0.0313 (2)0.50920 (18)0.27940 (13)0.0652 (5)
H29−0.11690.51800.30100.078*
C300.02879 (16)0.41391 (16)0.22286 (12)0.0546 (5)
H30−0.01430.35740.20730.065*
C310.15591 (15)0.40480 (14)0.18968 (10)0.0426 (4)
C320.46405 (18)0.2895 (2)0.05241 (14)0.0743 (6)
H32A0.54230.27830.07670.089*
H32B0.47190.3381−0.00170.089*
C330.44347 (17)0.1671 (2)0.03051 (13)0.0697 (6)
H33A0.50040.1358−0.02320.084*
H33B0.46250.11000.07870.084*
C340.22400 (15)0.20732 (15)0.09558 (10)0.0436 (4)
C350.24538 (14)0.10483 (15)0.16475 (10)0.0427 (4)
C360.25806 (17)−0.01527 (16)0.13810 (12)0.0552 (5)
H360.2531−0.03080.07930.066*
C370.27782 (18)−0.11157 (17)0.19745 (12)0.0597 (5)
H370.2865−0.19170.17930.072*
C380.28430 (17)−0.08643 (17)0.28335 (12)0.0538 (5)
C390.27395 (17)0.02883 (17)0.31220 (12)0.0556 (5)
H390.27990.04290.37110.067*
C400.25431 (16)0.12532 (16)0.25213 (11)0.0490 (4)
H400.24710.20490.27100.059*
C410.09707 (15)0.22610 (15)0.06247 (10)0.0421 (4)
C420.07212 (17)0.31129 (16)−0.00514 (11)0.0514 (4)
H420.13150.3569−0.02740.062*
C43−0.03962 (18)0.32917 (17)−0.03970 (12)0.0576 (5)
H43−0.05620.3861−0.08500.069*
C44−0.12525 (17)0.26093 (18)−0.00561 (12)0.0549 (5)
C45−0.10527 (17)0.17695 (17)0.06081 (12)0.0571 (5)
H45−0.16540.13200.08270.068*
C460.00684 (16)0.16015 (16)0.09501 (11)0.0517 (4)
H460.02180.10350.14070.062*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
F10.0564 (7)0.1096 (10)0.0900 (9)−0.0353 (7)0.0025 (6)0.0043 (7)
F20.1287 (11)0.0711 (8)0.0718 (8)−0.0411 (7)−0.0199 (7)0.0276 (6)
F30.1046 (9)0.0656 (8)0.0735 (8)−0.0146 (7)−0.0313 (7)0.0242 (6)
F40.0631 (7)0.1079 (10)0.0883 (8)−0.0183 (7)−0.0361 (6)0.0022 (7)
O10.0619 (8)0.0689 (8)0.0405 (6)−0.0249 (6)−0.0122 (5)−0.0023 (6)
O20.0485 (7)0.0683 (8)0.0417 (6)−0.0058 (6)0.0018 (5)−0.0001 (6)
N10.0378 (8)0.0530 (9)0.0492 (8)−0.0084 (6)−0.0108 (6)0.0025 (7)
N20.0389 (8)0.0498 (9)0.0487 (8)−0.0151 (6)−0.0060 (6)0.0026 (7)
C10.0395 (10)0.0734 (13)0.0640 (12)−0.0154 (9)−0.0145 (9)0.0116 (10)
C20.0364 (11)0.0765 (15)0.0919 (15)−0.0001 (10)−0.0083 (10)0.0099 (12)
C30.0440 (10)0.0498 (11)0.0653 (12)−0.0059 (8)−0.0001 (9)0.0067 (9)
C40.0637 (14)0.0513 (12)0.0888 (15)0.0019 (10)0.0100 (12)−0.0017 (11)
C50.0895 (17)0.0536 (13)0.0748 (14)−0.0141 (12)0.0033 (12)−0.0111 (11)
C60.0764 (14)0.0593 (13)0.0661 (13)−0.0179 (11)−0.0157 (10)−0.0071 (10)
C70.0525 (11)0.0519 (11)0.0588 (11)−0.0082 (9)−0.0135 (9)−0.0041 (9)
C80.0451 (10)0.0413 (10)0.0459 (9)−0.0088 (8)−0.0038 (7)0.0046 (8)
C90.0566 (13)0.1079 (19)0.0782 (14)−0.0296 (13)−0.0264 (11)0.0043 (13)
C100.0706 (14)0.0911 (16)0.0608 (12)−0.0395 (12)−0.0225 (10)0.0013 (11)
C110.0467 (10)0.0480 (10)0.0371 (9)−0.0110 (8)−0.0083 (7)−0.0018 (7)
C120.0438 (10)0.0447 (10)0.0363 (8)−0.0095 (8)−0.0050 (7)−0.0012 (7)
C130.0499 (11)0.0551 (11)0.0483 (10)−0.0109 (8)−0.0107 (8)0.0071 (8)
C140.0599 (12)0.0615 (12)0.0518 (11)−0.0228 (10)−0.0047 (9)0.0095 (9)
C150.0424 (11)0.0655 (12)0.0563 (11)−0.0206 (9)0.0013 (8)−0.0073 (10)
C160.0442 (11)0.0588 (12)0.0624 (12)−0.0074 (9)−0.0110 (9)−0.0016 (9)
C170.0485 (11)0.0541 (11)0.0468 (10)−0.0110 (8)−0.0092 (8)0.0064 (8)
C180.0427 (9)0.0472 (10)0.0391 (9)−0.0143 (8)−0.0042 (7)−0.0016 (7)
C190.0656 (12)0.0559 (12)0.0445 (10)−0.0131 (9)0.0004 (9)−0.0025 (9)
C200.0686 (13)0.0464 (11)0.0621 (12)−0.0116 (9)−0.0075 (10)−0.0009 (9)
C210.0670 (12)0.0585 (12)0.0529 (11)−0.0301 (10)−0.0146 (9)0.0170 (9)
C220.0660 (12)0.0643 (13)0.0430 (10)−0.0277 (10)0.0024 (8)0.0006 (9)
C230.0515 (10)0.0500 (11)0.0450 (10)−0.0170 (8)0.0008 (8)−0.0026 (8)
C240.0399 (10)0.0705 (13)0.0561 (11)−0.0206 (9)−0.0105 (8)0.0131 (10)
C250.0587 (13)0.0767 (14)0.0719 (13)−0.0374 (11)−0.0227 (10)0.0111 (11)
C260.0619 (12)0.0502 (11)0.0498 (10)−0.0235 (9)−0.0193 (9)0.0097 (8)
C270.0999 (17)0.0533 (12)0.0590 (12)−0.0316 (12)−0.0225 (12)0.0012 (10)
C280.0971 (17)0.0557 (13)0.0596 (12)−0.0133 (12)−0.0038 (12)−0.0078 (10)
C290.0640 (13)0.0629 (13)0.0628 (12)−0.0107 (10)0.0038 (10)−0.0055 (10)
C300.0518 (11)0.0551 (11)0.0574 (11)−0.0175 (9)−0.0010 (8)−0.0056 (9)
C310.0453 (10)0.0428 (10)0.0414 (9)−0.0131 (8)−0.0088 (7)0.0059 (7)
C320.0443 (12)0.1052 (18)0.0729 (14)−0.0216 (11)−0.0025 (10)0.0066 (12)
C330.0412 (11)0.0929 (16)0.0624 (12)0.0007 (10)0.0055 (9)0.0044 (11)
C340.0413 (9)0.0474 (10)0.0403 (9)−0.0091 (8)−0.0026 (7)0.0001 (7)
C350.0381 (9)0.0475 (10)0.0423 (9)−0.0084 (7)−0.0077 (7)0.0006 (8)
C360.0668 (12)0.0527 (11)0.0461 (10)−0.0095 (9)−0.0138 (9)−0.0029 (9)
C370.0731 (13)0.0449 (11)0.0612 (12)−0.0081 (9)−0.0176 (10)−0.0006 (9)
C380.0541 (11)0.0534 (12)0.0537 (11)−0.0079 (9)−0.0169 (8)0.0129 (9)
C390.0619 (12)0.0622 (13)0.0446 (10)−0.0103 (9)−0.0194 (8)0.0031 (9)
C400.0518 (10)0.0483 (10)0.0483 (10)−0.0097 (8)−0.0136 (8)−0.0019 (8)
C410.0445 (10)0.0443 (10)0.0376 (9)−0.0097 (8)−0.0063 (7)−0.0021 (7)
C420.0523 (11)0.0521 (11)0.0510 (10)−0.0145 (8)−0.0092 (8)0.0074 (8)
C430.0587 (12)0.0618 (12)0.0510 (10)−0.0069 (10)−0.0166 (9)0.0096 (9)
C440.0470 (11)0.0640 (12)0.0561 (11)−0.0087 (9)−0.0183 (9)−0.0079 (10)
C450.0509 (11)0.0636 (12)0.0615 (12)−0.0213 (9)−0.0104 (9)−0.0005 (10)
C460.0541 (11)0.0553 (11)0.0489 (10)−0.0178 (9)−0.0117 (8)0.0078 (8)

Geometric parameters (Å, °)

F1—C151.356 (2)C19—H190.9300
F2—C211.3575 (19)C20—C211.366 (2)
F3—C381.3595 (19)C20—H200.9300
F4—C441.362 (2)C21—C221.357 (3)
O1—C111.4229 (18)C22—C231.386 (2)
O1—C101.437 (2)C22—H220.9300
O2—C341.4270 (18)C23—H230.9300
O2—C331.436 (2)C24—C251.347 (3)
N1—C11.389 (2)C24—C321.493 (3)
N1—C81.398 (2)C25—C261.424 (3)
N1—C111.477 (2)C25—H250.9300
N2—C311.394 (2)C26—C271.398 (3)
N2—C241.395 (2)C26—C311.407 (2)
N2—C341.479 (2)C27—C281.367 (3)
C1—C21.352 (3)C27—H270.9300
C1—C91.493 (3)C28—C291.390 (3)
C2—C31.418 (3)C28—H280.9300
C2—H20.9300C29—C301.375 (2)
C3—C41.397 (3)C29—H290.9300
C3—C81.405 (2)C30—C311.389 (2)
C4—C51.363 (3)C30—H300.9300
C4—H40.9300C32—C331.498 (3)
C5—C61.384 (3)C32—H32A0.9700
C5—H50.9300C32—H32B0.9700
C6—C71.379 (2)C33—H33A0.9700
C6—H60.9300C33—H33B0.9700
C7—C81.388 (2)C34—C411.525 (2)
C7—H70.9300C34—C351.528 (2)
C9—C101.500 (3)C35—C401.379 (2)
C9—H9A0.9700C35—C361.391 (2)
C9—H9B0.9700C36—C371.378 (2)
C10—H10A0.9700C36—H360.9300
C10—H10B0.9700C37—C381.363 (2)
C11—C121.531 (2)C37—H370.9300
C11—C181.531 (2)C38—C391.355 (2)
C12—C171.377 (2)C39—C401.387 (2)
C12—C131.388 (2)C39—H390.9300
C13—C141.378 (2)C40—H400.9300
C13—H130.9300C41—C461.384 (2)
C14—C151.363 (3)C41—C421.390 (2)
C14—H140.9300C42—C431.382 (2)
C15—C161.364 (2)C42—H420.9300
C16—C171.391 (2)C43—C441.368 (3)
C16—H160.9300C43—H430.9300
C17—H170.9300C44—C451.360 (2)
C18—C231.383 (2)C45—C461.384 (2)
C18—C191.385 (2)C45—H450.9300
C19—C201.381 (2)C46—H460.9300
C11—O1—C10113.98 (13)C23—C22—H22120.7
C34—O2—C33114.17 (13)C18—C23—C22120.77 (16)
C1—N1—C8108.31 (14)C18—C23—H23119.6
C1—N1—C11122.61 (14)C22—C23—H23119.6
C8—N1—C11127.83 (13)C25—C24—N2109.24 (16)
C31—N2—C24108.11 (14)C25—C24—C32130.84 (18)
C31—N2—C34128.02 (13)N2—C24—C32119.73 (17)
C24—N2—C34122.53 (14)C24—C25—C26108.43 (16)
C2—C1—N1108.87 (17)C24—C25—H25125.8
C2—C1—C9131.53 (18)C26—C25—H25125.8
N1—C1—C9119.44 (17)C27—C26—C31119.42 (17)
C1—C2—C3108.76 (16)C27—C26—C25133.75 (18)
C1—C2—H2125.6C31—C26—C25106.82 (16)
C3—C2—H2125.6C28—C27—C26119.34 (18)
C4—C3—C8118.98 (18)C28—C27—H27120.3
C4—C3—C2134.24 (18)C26—C27—H27120.3
C8—C3—C2106.78 (16)C27—C28—C29120.42 (19)
C5—C4—C3119.63 (19)C27—C28—H28119.8
C5—C4—H4120.2C29—C28—H28119.8
C3—C4—H4120.2C30—C29—C28121.94 (19)
C4—C5—C6120.60 (19)C30—C29—H29119.0
C4—C5—H5119.7C28—C29—H29119.0
C6—C5—H5119.7C29—C30—C31117.86 (17)
C7—C6—C5121.8 (2)C29—C30—H30121.1
C7—C6—H6119.1C31—C30—H30121.1
C5—C6—H6119.1C30—C31—N2131.60 (15)
C6—C7—C8117.54 (17)C30—C31—C26120.99 (16)
C6—C7—H7121.2N2—C31—C26107.39 (14)
C8—C7—H7121.2C24—C32—C33111.25 (16)
C7—C8—N1131.33 (15)C24—C32—H32A109.4
C7—C8—C3121.39 (16)C33—C32—H32A109.4
N1—C8—C3107.28 (15)C24—C32—H32B109.4
C1—C9—C10111.49 (16)C33—C32—H32B109.4
C1—C9—H9A109.3H32A—C32—H32B108.0
C10—C9—H9A109.3O2—C33—C32110.98 (16)
C1—C9—H9B109.3O2—C33—H33A109.4
C10—C9—H9B109.3C32—C33—H33A109.4
H9A—C9—H9B108.0O2—C33—H33B109.4
O1—C10—C9110.03 (16)C32—C33—H33B109.4
O1—C10—H10A109.7H33A—C33—H33B108.0
C9—C10—H10A109.7O2—C34—N2107.28 (13)
O1—C10—H10B109.7O2—C34—C41104.15 (12)
C9—C10—H10B109.7N2—C34—C41110.25 (13)
H10A—C10—H10B108.2O2—C34—C35109.44 (12)
O1—C11—N1107.82 (12)N2—C34—C35111.28 (13)
O1—C11—C12103.37 (12)C41—C34—C35113.99 (13)
N1—C11—C12110.13 (13)C40—C35—C36118.30 (15)
O1—C11—C18109.93 (13)C40—C35—C34123.24 (15)
N1—C11—C18111.30 (12)C36—C35—C34118.45 (14)
C12—C11—C18113.86 (13)C37—C36—C35121.08 (16)
C17—C12—C13118.51 (15)C37—C36—H36119.5
C17—C12—C11123.30 (15)C35—C36—H36119.5
C13—C12—C11118.12 (14)C38—C37—C36118.38 (17)
C14—C13—C12121.31 (16)C38—C37—H37120.8
C14—C13—H13119.3C36—C37—H37120.8
C12—C13—H13119.3C39—C38—F3118.82 (16)
C15—C14—C13118.20 (17)C39—C38—C37122.69 (17)
C15—C14—H14120.9F3—C38—C37118.49 (17)
C13—C14—H14120.9C38—C39—C40118.64 (16)
F1—C15—C14118.70 (17)C38—C39—H39120.7
F1—C15—C16118.47 (17)C40—C39—H39120.7
C14—C15—C16122.82 (16)C35—C40—C39120.88 (16)
C15—C16—C17118.25 (17)C35—C40—H40119.6
C15—C16—H16120.9C39—C40—H40119.6
C17—C16—H16120.9C46—C41—C42118.43 (16)
C12—C17—C16120.92 (17)C46—C41—C34123.08 (15)
C12—C17—H17119.5C42—C41—C34118.47 (15)
C16—C17—H17119.5C43—C42—C41120.93 (17)
C23—C18—C19118.40 (15)C43—C42—H42119.5
C23—C18—C11122.97 (15)C41—C42—H42119.5
C19—C18—C11118.63 (14)C44—C43—C42118.30 (17)
C20—C19—C18121.29 (16)C44—C43—H43120.8
C20—C19—H19119.4C42—C43—H43120.8
C18—C19—H19119.4C45—C44—F4118.61 (17)
C21—C20—C19118.15 (17)C45—C44—C43122.87 (17)
C21—C20—H20120.9F4—C44—C43118.51 (17)
C19—C20—H20120.9C44—C45—C46118.27 (17)
C22—C21—F2118.94 (17)C44—C45—H45120.9
C22—C21—C20122.65 (17)C46—C45—H45120.9
F2—C21—C20118.41 (18)C41—C46—C45121.21 (17)
C21—C22—C23118.69 (16)C41—C46—H46119.4
C21—C22—H22120.7C45—C46—H46119.4
C8—N1—C1—C2−1.1 (2)C31—N2—C24—C25−0.7 (2)
C11—N1—C1—C2−169.22 (15)C34—N2—C24—C25−168.44 (15)
C8—N1—C1—C9−176.91 (16)C31—N2—C24—C32−176.31 (16)
C11—N1—C1—C915.0 (2)C34—N2—C24—C3215.9 (2)
N1—C1—C2—C30.7 (2)N2—C24—C25—C260.1 (2)
C9—C1—C2—C3175.8 (2)C32—C24—C25—C26175.05 (19)
C1—C2—C3—C4179.9 (2)C24—C25—C26—C27−178.4 (2)
C1—C2—C3—C8−0.1 (2)C24—C25—C26—C310.5 (2)
C8—C3—C4—C5−0.1 (3)C31—C26—C27—C28−0.8 (3)
C2—C3—C4—C5180.0 (2)C25—C26—C27—C28178.0 (2)
C3—C4—C5—C6−0.1 (3)C26—C27—C28—C290.8 (3)
C4—C5—C6—C70.7 (3)C27—C28—C29—C300.5 (3)
C5—C6—C7—C8−1.2 (3)C28—C29—C30—C31−1.7 (3)
C6—C7—C8—N1−178.82 (17)C29—C30—C31—N2−176.50 (17)
C6—C7—C8—C31.0 (3)C29—C30—C31—C261.7 (3)
C1—N1—C8—C7−179.14 (18)C24—N2—C31—C30179.38 (18)
C11—N1—C8—C7−11.8 (3)C34—N2—C31—C30−13.7 (3)
C1—N1—C8—C31.02 (18)C24—N2—C31—C261.02 (18)
C11—N1—C8—C3168.35 (15)C34—N2—C31—C26167.89 (14)
C4—C3—C8—C7−0.4 (3)C27—C26—C31—C30−0.4 (3)
C2—C3—C8—C7179.56 (16)C25—C26—C31—C30−179.52 (16)
C4—C3—C8—N1179.47 (16)C27—C26—C31—N2178.13 (15)
C2—C3—C8—N1−0.59 (19)C25—C26—C31—N2−0.95 (19)
C2—C1—C9—C10163.8 (2)C25—C24—C32—C33164.7 (2)
N1—C1—C9—C10−21.5 (3)N2—C24—C32—C33−20.8 (3)
C11—O1—C10—C9−66.94 (19)C34—O2—C33—C32−66.25 (19)
C1—C9—C10—O145.0 (2)C24—C32—C33—O243.6 (2)
C10—O1—C11—N156.31 (18)C33—O2—C34—N256.57 (18)
C10—O1—C11—C12172.92 (14)C33—O2—C34—C41173.47 (14)
C10—O1—C11—C18−65.18 (18)C33—O2—C34—C35−64.28 (18)
C1—N1—C11—O1−30.2 (2)C31—N2—C34—O2163.30 (14)
C8—N1—C11—O1164.11 (14)C24—N2—C34—O2−31.53 (19)
C1—N1—C11—C12−142.33 (15)C31—N2—C34—C4150.5 (2)
C8—N1—C11—C1252.0 (2)C24—N2—C34—C41−144.34 (15)
C1—N1—C11—C1890.43 (17)C31—N2—C34—C35−77.02 (19)
C8—N1—C11—C18−75.26 (19)C24—N2—C34—C3588.15 (17)
O1—C11—C12—C17117.65 (16)O2—C34—C35—C40129.85 (16)
N1—C11—C12—C17−127.39 (16)N2—C34—C35—C4011.5 (2)
C18—C11—C12—C17−1.6 (2)C41—C34—C35—C40−114.00 (17)
O1—C11—C12—C13−59.36 (18)O2—C34—C35—C36−49.3 (2)
N1—C11—C12—C1355.61 (18)N2—C34—C35—C36−167.72 (14)
C18—C11—C12—C13−178.58 (14)C41—C34—C35—C3666.83 (19)
C17—C12—C13—C14−0.3 (2)C40—C35—C36—C370.6 (3)
C11—C12—C13—C14176.84 (15)C34—C35—C36—C37179.83 (16)
C12—C13—C14—C150.0 (3)C35—C36—C37—C380.2 (3)
C13—C14—C15—F1179.12 (16)C36—C37—C38—C39−1.0 (3)
C13—C14—C15—C160.3 (3)C36—C37—C38—F3179.34 (16)
F1—C15—C16—C17−179.05 (16)F3—C38—C39—C40−179.46 (15)
C14—C15—C16—C17−0.2 (3)C37—C38—C39—C400.9 (3)
C13—C12—C17—C160.4 (2)C36—C35—C40—C39−0.7 (2)
C11—C12—C17—C16−176.61 (15)C34—C35—C40—C39−179.91 (15)
C15—C16—C17—C12−0.1 (3)C38—C39—C40—C350.0 (3)
O1—C11—C18—C23134.65 (16)O2—C34—C41—C46122.00 (16)
N1—C11—C18—C2315.3 (2)N2—C34—C41—C46−123.20 (16)
C12—C11—C18—C23−109.93 (17)C35—C34—C41—C462.8 (2)
O1—C11—C18—C19−45.0 (2)O2—C34—C41—C42−56.34 (18)
N1—C11—C18—C19−164.36 (15)N2—C34—C41—C4258.46 (18)
C12—C11—C18—C1970.44 (19)C35—C34—C41—C42−175.54 (14)
C23—C18—C19—C201.2 (3)C46—C41—C42—C43−0.5 (2)
C11—C18—C19—C20−179.11 (16)C34—C41—C42—C43177.87 (15)
C18—C19—C20—C210.2 (3)C41—C42—C43—C440.1 (3)
C19—C20—C21—C22−1.5 (3)C42—C43—C44—C450.3 (3)
C19—C20—C21—F2178.64 (16)C42—C43—C44—F4179.35 (16)
F2—C21—C22—C23−178.82 (16)F4—C44—C45—C46−179.18 (15)
C20—C21—C22—C231.3 (3)C43—C44—C45—C46−0.1 (3)
C19—C18—C23—C22−1.4 (3)C42—C41—C46—C450.7 (2)
C11—C18—C23—C22178.95 (15)C34—C41—C46—C45−177.62 (15)
C21—C22—C23—C180.2 (3)C44—C45—C46—C41−0.4 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C14—H14···Cg3i0.932.883.769 (2)159
C29—H29···Cg5ii0.932.933.747 (2)148
C43—H43···Cg11iii0.932.793.695 (2)165
C40—H40···Cg90.932.743.3790 (7)127

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SI2115).

References

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  • Lee, H., Knobler, C. B. & Hawthorne, M. F. (2000). Chem. Commun. pp. 2485–2486.
  • Monckton, J. E. & McCormick, D. A. (2002). J. Neurophysiol. pp. 2124–2136. [PubMed]
  • Sakamoto, T., Kondo, Y. & Yamanaka, H. (1988). Heterocycles, 27, 2225–2249.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2003). J. Appl. Cryst.36, 7–13.

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