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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

3-(4-Fluoro­phen­yl)-2-(2-naphth­yl­oxy)-4-oxo-5-phenyl-4,5-di­hydro-3H-pyrrolo[3,2-d]pyrimidine-7-carbo­nitrile

aInstitute of Medicinal Chemistry, Yunyang Medical College, Shiyan Hubei 442000, People's Republic of China, bDepartment of Pharmacy, Affiliated Renmin Hospital, Yunyang Medical College, Shiyan Hubei 442000, People's Republic of China, and cDepartment of Pharmacy, Taihe Hospital of Yunyang Medical College and Institute of Medicinal Chemistry, Yunyang Medical College, Shiyan Hubei 442000, People's Republic of China
*Correspondence e-mail: huyangg111@yahoo.com.cn

(Received 26 September 2009; accepted 29 September 2009; online 3 October 2009)

The title compound, C29H17FN4O2, may be used as a new precursor for obtaining bioactive mol­ecules. There are two crystallographically independent mol­ecules in the asymmetric unit. The phenyl ring, 4-fluoro­phenyl ring and 2-naphth­yloxy ring are twisted with respect to the pyrrolopyrimidine ring by 52.30 (11)/49.05 (11), 80.94 (10)/88.36 (10) and 60.58 (7)/83.76 (7)°, respectively. The crystal packing is stabilized by weak C—H⋯N hydrogen bonds.

Related literature

For the biological activity of pyrimidinone derivatives, see: Kondo et al. (1986[Kondo, T., Okamoto, K., Ohgi, T. & Goto, T. (1986). Tetrahedron, 42, 207-213.]) and for their pharmaceutical activity, see: Bayomi et al. (1986[Bayomi, S. M., El-Emam, A. A., Moustafa, M. A. & El-Kerdawy, M. M. (1986). Taiwan Yaoxue Zazhi, 38, 129-135.]); Ding et al. (2004[Ding, M. W., Xu, S. Z. & Zhao, J. F. (2004). J. Org. Chem. 69, 8366-8371.]). For related structures, see: He et al. (2007[He, P., Peng, X.-M. & Li, G.-H. (2007). Acta Cryst. E63, o4884.]); Hu et al. (2005[Hu, Y.-G., Li, G.-H., Tian, J.-H., Ding, M.-W. & He, H.-W. (2005). Acta Cryst. E61, o3266-o3268.], 2006[Hu, Y.-G., Zheng, A.-H. & Li, G.-H. (2006). Acta Cryst. E62, o1457-o1459.], 2007[Hu, Y.-G., Li, G.-H. & Zhou, M.-H. (2007). Acta Cryst. E63, o1836-o1838.]).

[Scheme 1]

Experimental

Crystal data
  • C29H17FN4O2

  • Mr = 472.47

  • Triclinic, [P \overline 1]

  • a = 9.8522 (16) Å

  • b = 14.549 (2) Å

  • c = 16.792 (3) Å

  • α = 101.755 (3)°

  • β = 90.840 (3)°

  • γ = 103.789 (3)°

  • V = 2283.5 (6) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 298 K

  • 0.16 × 0.12 × 0.10 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.985, Tmax = 0.991

  • 14836 measured reflections

  • 8839 independent reflections

  • 5302 reflections with I > 2σ(I)

  • Rint = 0.082

Refinement
  • R[F2 > 2σ(F2)] = 0.056

  • wR(F2) = 0.129

  • S = 0.93

  • 8839 reflections

  • 649 parameters

  • H-atom parameters constrained

  • Δρmax = 0.22 e Å−3

  • Δρmin = −0.20 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C45—H45⋯N4i 0.93 2.48 3.312 (3) 150
C15—H15⋯N8ii 0.93 2.48 3.294 (3) 147
Symmetry codes: (i) x, y+1, z; (ii) x, y-1, z.

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2001[Bruker (2001). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

Derivatives of pyrimidinone are attracting increasing attention in the synthetic chemistry community because of the important role played by such systems in many natural products, also in antibiotics and drugs (Kondo et al.,1986; Bayomi et al., 1986; Ding et al., 2004). Recently, aza-Wittig reaction of functionalized iminophosphoranes with isocyanates were applied to produce carbodiimides able to undergo a plethora of heterocyclization reactions (Hu et al., 2005, 2006, 2007 and He et al., 2007). As a part of our ongoing investigations on the preparation of the heterocyclic compounds, we have synthesized and structurally characterized the title compound. In the crystal structure of title compound two crystallographically independent molecules are found in the asymmetric unit. All ring atoms of pyrrolopyrimidine ring system are coplanar, with a maximum deviation of -0.024Å for atom C12. The phenyl ring and 4-fluorophenyl ring, 2-naphthalenyloxy ring are twisted with the pyrrolopyrimidine rings by 52.30 (11)/49.05 (11)°, 80.94 (10)/88.36 (10)°, 60.58 (7)/83.76 (7)°,respectively. The crystal packing is mainly stabilized by C—H···N (Table 1).

Related literature top

For the biological activity of pyrimidinone derivatives, see: Kondo et al. (1986) and for their pharmaceutical activity, see: Bayomi et al. (1986); Ding et al. (2004). For related structures, see: He et al. (2007); Hu et al. (2005, 2006, 2007).

Experimental top

The title compound was obtained in excellent yield via aza-Wittig reaction. Crystals suitable for single-crystal X-ray diffraction were obtained by recrystallization from a mixed solvent of ethanol and dichloromethane (1:2 v/v) at room temperature.

Refinement top

All H-atoms were positioned geometrically and refined using a riding model with C—H = 0.93 Å and Uiso=1.2Ueq(C).

Structure description top

Derivatives of pyrimidinone are attracting increasing attention in the synthetic chemistry community because of the important role played by such systems in many natural products, also in antibiotics and drugs (Kondo et al.,1986; Bayomi et al., 1986; Ding et al., 2004). Recently, aza-Wittig reaction of functionalized iminophosphoranes with isocyanates were applied to produce carbodiimides able to undergo a plethora of heterocyclization reactions (Hu et al., 2005, 2006, 2007 and He et al., 2007). As a part of our ongoing investigations on the preparation of the heterocyclic compounds, we have synthesized and structurally characterized the title compound. In the crystal structure of title compound two crystallographically independent molecules are found in the asymmetric unit. All ring atoms of pyrrolopyrimidine ring system are coplanar, with a maximum deviation of -0.024Å for atom C12. The phenyl ring and 4-fluorophenyl ring, 2-naphthalenyloxy ring are twisted with the pyrrolopyrimidine rings by 52.30 (11)/49.05 (11)°, 80.94 (10)/88.36 (10)°, 60.58 (7)/83.76 (7)°,respectively. The crystal packing is mainly stabilized by C—H···N (Table 1).

For the biological activity of pyrimidinone derivatives, see: Kondo et al. (1986) and for their pharmaceutical activity, see: Bayomi et al. (1986); Ding et al. (2004). For related structures, see: He et al. (2007); Hu et al. (2005, 2006, 2007).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing the atom-labeling scheme.
3-(4-Fluorophenyl)-2-(2-naphthyloxy)-4-oxo-5-phenyl-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidine-7-carbonitrile top
Crystal data top
C29H17FN4O2Z = 4
Mr = 472.47F(000) = 976
Triclinic, P1Dx = 1.374 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.8522 (16) ÅCell parameters from 2855 reflections
b = 14.549 (2) Åθ = 2.1–23.7°
c = 16.792 (3) ŵ = 0.09 mm1
α = 101.755 (3)°T = 298 K
β = 90.840 (3)°Block, colorless
γ = 103.789 (3)°0.16 × 0.12 × 0.10 mm
V = 2283.5 (6) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer
8839 independent reflections
Radiation source: fine-focus sealed tube5302 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.082
φ and ω scansθmax = 26.0°, θmin = 1.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
h = 1012
Tmin = 0.985, Tmax = 0.991k = 1717
14836 measured reflectionsl = 2020
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.129H-atom parameters constrained
S = 0.93 w = 1/[σ2(Fo2) + (0.0375P)2]
where P = (Fo2 + 2Fc2)/3
8839 reflections(Δ/σ)max = 0.001
649 parametersΔρmax = 0.22 e Å3
0 restraintsΔρmin = 0.20 e Å3
Crystal data top
C29H17FN4O2γ = 103.789 (3)°
Mr = 472.47V = 2283.5 (6) Å3
Triclinic, P1Z = 4
a = 9.8522 (16) ÅMo Kα radiation
b = 14.549 (2) ŵ = 0.09 mm1
c = 16.792 (3) ÅT = 298 K
α = 101.755 (3)°0.16 × 0.12 × 0.10 mm
β = 90.840 (3)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
8839 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
5302 reflections with I > 2σ(I)
Tmin = 0.985, Tmax = 0.991Rint = 0.082
14836 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0560 restraints
wR(F2) = 0.129H-atom parameters constrained
S = 0.93Δρmax = 0.22 e Å3
8839 reflectionsΔρmin = 0.20 e Å3
649 parameters
Special details top

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) top
xyzUiso*/Ueq
C10.6132 (3)0.62617 (17)0.92978 (14)0.0490 (6)
H10.53940.58290.94660.059*
C20.5894 (3)0.67826 (17)0.87454 (15)0.0498 (6)
H20.49870.66900.85270.060*
C30.6992 (3)0.74576 (16)0.84978 (14)0.0423 (6)
C40.6778 (3)0.80169 (19)0.79335 (15)0.0591 (7)
H40.58790.79400.77090.071*
C50.7866 (3)0.8665 (2)0.77143 (16)0.0661 (8)
H50.77020.90260.73420.079*
C60.9217 (3)0.8795 (2)0.80395 (17)0.0680 (8)
H60.99500.92460.78870.082*
C70.9477 (3)0.82632 (18)0.85846 (15)0.0557 (7)
H71.03870.83500.87960.067*
C80.8371 (3)0.75842 (16)0.88259 (13)0.0415 (6)
C90.8599 (2)0.70201 (16)0.93887 (13)0.0425 (6)
H90.94990.70850.96060.051*
C100.7502 (3)0.63887 (16)0.96067 (13)0.0411 (6)
C110.7475 (2)0.49336 (16)1.00458 (14)0.0389 (6)
C120.7632 (2)0.35673 (16)1.06705 (14)0.0387 (6)
C130.7014 (2)0.30076 (15)0.98939 (13)0.0355 (5)
C140.6725 (2)0.34463 (15)0.92770 (13)0.0360 (5)
C150.6130 (2)0.18391 (17)0.88114 (13)0.0437 (6)
H150.58040.12290.84750.052*
C160.6166 (2)0.27031 (16)0.85905 (13)0.0397 (6)
C170.5731 (3)0.28410 (17)0.78179 (15)0.0459 (6)
C180.6789 (2)0.12700 (16)1.00212 (14)0.0407 (6)
C190.7474 (3)0.05891 (18)0.96680 (16)0.0558 (7)
H190.78410.06090.91630.067*
C200.7614 (3)0.0126 (2)1.0067 (2)0.0724 (9)
H200.80700.05940.98300.087*
C210.7080 (3)0.0144 (2)1.0813 (2)0.0742 (9)
H210.71760.06271.10820.089*
C220.6406 (3)0.0541 (2)1.11643 (16)0.0663 (8)
H220.60610.05291.16760.080*
C230.6239 (3)0.12471 (17)1.07634 (14)0.0542 (7)
H230.57580.17031.09940.065*
C240.8394 (3)0.52226 (15)1.14719 (13)0.0378 (5)
C250.9802 (3)0.54426 (17)1.16563 (15)0.0512 (7)
H251.03850.51961.12850.061*
C261.0361 (3)0.60350 (19)1.23994 (17)0.0600 (7)
H261.13190.61921.25350.072*
C270.9470 (3)0.63836 (17)1.29277 (15)0.0546 (7)
C280.8073 (3)0.61833 (17)1.27538 (15)0.0532 (7)
H280.74980.64401.31250.064*
C290.7516 (3)0.55902 (16)1.20148 (14)0.0456 (6)
H290.65570.54391.18830.055*
C300.6220 (3)0.69583 (19)0.48011 (16)0.0573 (7)
H300.55940.70100.44030.069*
C310.5805 (3)0.63259 (19)0.52901 (16)0.0596 (7)
H310.48900.59470.52290.072*
C320.6745 (3)0.62370 (17)0.58909 (14)0.0463 (6)
C330.6349 (3)0.55678 (19)0.64114 (17)0.0669 (8)
H330.54370.51860.63690.080*
C340.7312 (4)0.5489 (2)0.69714 (17)0.0720 (9)
H340.70520.50550.73120.086*
C350.8680 (4)0.6056 (2)0.70342 (17)0.0748 (9)
H350.93280.59890.74140.090*
C360.9086 (3)0.6701 (2)0.65539 (15)0.0631 (8)
H361.00020.70790.66100.076*
C370.8132 (3)0.68024 (16)0.59734 (14)0.0431 (6)
C380.8538 (3)0.74723 (17)0.54546 (14)0.0486 (6)
H380.94450.78620.55030.058*
C390.7584 (3)0.75314 (17)0.48932 (14)0.0448 (6)
C400.7721 (2)0.90035 (16)0.44752 (14)0.0399 (6)
C410.6952 (2)1.02363 (15)0.51638 (12)0.0353 (5)
C420.7355 (2)1.07974 (15)0.45980 (13)0.0359 (5)
C430.8047 (2)1.04576 (16)0.38944 (14)0.0409 (6)
C440.6360 (2)1.07937 (16)0.57945 (13)0.0383 (6)
C450.6438 (2)1.16720 (17)0.55851 (13)0.0440 (6)
H450.61271.21810.58920.053*
C460.5761 (2)1.05029 (17)0.64986 (14)0.0430 (6)
C470.7274 (2)1.25012 (17)0.44751 (14)0.0425 (6)
C480.7886 (3)1.34087 (17)0.49336 (16)0.0539 (7)
H480.81551.34890.54820.065*
C490.8099 (3)1.41970 (19)0.4573 (2)0.0702 (9)
H490.84961.48150.48800.084*
C500.7721 (3)1.4067 (2)0.3757 (2)0.0780 (10)
H500.78831.45970.35110.094*
C510.7108 (3)1.3161 (2)0.33079 (18)0.0715 (9)
H510.68531.30800.27580.086*
C520.6866 (3)1.23672 (19)0.36637 (15)0.0554 (7)
H520.64361.17530.33610.067*
C530.8782 (2)0.90428 (15)0.31605 (13)0.0363 (5)
C540.7934 (3)0.85468 (17)0.24827 (14)0.0475 (6)
H540.69770.85070.24780.057*
C550.8494 (3)0.81039 (17)0.18027 (14)0.0494 (6)
H550.79270.77590.13390.059*
C560.9890 (3)0.81875 (17)0.18328 (14)0.0440 (6)
C571.0759 (3)0.86866 (19)0.24921 (15)0.0582 (7)
H571.17180.87360.24870.070*
C581.0190 (3)0.91202 (19)0.31723 (14)0.0528 (7)
H581.07620.94620.36350.063*
F11.00295 (19)0.69609 (12)1.36557 (9)0.0862 (5)
F21.04529 (16)0.77395 (11)0.11711 (8)0.0686 (4)
N10.6958 (2)0.44287 (13)0.93398 (11)0.0402 (5)
N20.78044 (19)0.45772 (12)1.07043 (10)0.0375 (5)
N30.66453 (19)0.20168 (13)0.95990 (11)0.0403 (5)
N40.5398 (3)0.29764 (17)0.72066 (13)0.0658 (7)
N50.71351 (19)0.93223 (13)0.51206 (11)0.0401 (5)
N60.81678 (19)0.94956 (13)0.38718 (10)0.0386 (5)
N70.7039 (2)1.16818 (13)0.48610 (11)0.0418 (5)
N80.5282 (2)1.02686 (16)0.70593 (12)0.0638 (7)
O10.77772 (18)0.59064 (11)1.02224 (9)0.0511 (4)
O20.79870 (18)0.32927 (11)1.12612 (9)0.0526 (5)
O30.80000 (19)0.81309 (12)0.43311 (9)0.0562 (5)
O40.85016 (19)1.08711 (12)0.33598 (10)0.0592 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0468 (16)0.0467 (15)0.0597 (17)0.0125 (12)0.0161 (13)0.0236 (13)
C20.0431 (15)0.0522 (16)0.0632 (17)0.0209 (12)0.0056 (13)0.0218 (14)
C30.0512 (16)0.0401 (14)0.0428 (14)0.0196 (12)0.0125 (12)0.0148 (11)
C40.0720 (19)0.0639 (18)0.0542 (17)0.0303 (15)0.0083 (15)0.0253 (14)
C50.089 (2)0.0643 (19)0.0574 (18)0.0242 (17)0.0155 (17)0.0354 (15)
C60.082 (2)0.0605 (18)0.066 (2)0.0102 (16)0.0277 (17)0.0307 (16)
C70.0564 (17)0.0529 (16)0.0573 (17)0.0063 (13)0.0110 (13)0.0187 (14)
C80.0521 (16)0.0382 (13)0.0359 (13)0.0129 (11)0.0108 (12)0.0092 (11)
C90.0462 (15)0.0412 (14)0.0426 (14)0.0142 (12)0.0002 (11)0.0108 (11)
C100.0607 (17)0.0332 (13)0.0354 (13)0.0178 (12)0.0058 (12)0.0130 (11)
C110.0498 (15)0.0317 (13)0.0389 (14)0.0122 (11)0.0104 (12)0.0129 (11)
C120.0433 (14)0.0375 (13)0.0398 (14)0.0118 (11)0.0120 (11)0.0156 (11)
C130.0444 (14)0.0321 (12)0.0335 (13)0.0139 (10)0.0095 (11)0.0095 (10)
C140.0421 (14)0.0341 (13)0.0347 (13)0.0123 (10)0.0093 (11)0.0098 (11)
C150.0567 (16)0.0386 (14)0.0337 (14)0.0103 (12)0.0058 (12)0.0045 (11)
C160.0490 (15)0.0408 (14)0.0312 (13)0.0140 (11)0.0033 (11)0.0088 (11)
C170.0528 (16)0.0426 (15)0.0413 (15)0.0108 (12)0.0064 (13)0.0075 (12)
C180.0509 (15)0.0311 (13)0.0422 (14)0.0113 (11)0.0041 (12)0.0112 (11)
C190.0741 (19)0.0441 (15)0.0544 (16)0.0224 (14)0.0172 (14)0.0127 (13)
C200.087 (2)0.0472 (17)0.093 (2)0.0297 (16)0.0126 (19)0.0214 (17)
C210.093 (2)0.0516 (18)0.086 (2)0.0143 (17)0.0049 (19)0.0391 (17)
C220.093 (2)0.0533 (18)0.0549 (18)0.0081 (16)0.0102 (16)0.0266 (15)
C230.0732 (19)0.0423 (15)0.0527 (16)0.0175 (13)0.0202 (14)0.0181 (13)
C240.0497 (15)0.0302 (12)0.0365 (13)0.0113 (11)0.0033 (12)0.0126 (11)
C250.0485 (17)0.0499 (15)0.0562 (17)0.0164 (13)0.0072 (13)0.0081 (13)
C260.0545 (17)0.0563 (17)0.069 (2)0.0145 (14)0.0126 (15)0.0141 (15)
C270.084 (2)0.0390 (15)0.0442 (16)0.0216 (15)0.0121 (16)0.0091 (13)
C280.074 (2)0.0480 (16)0.0422 (16)0.0254 (14)0.0077 (14)0.0091 (13)
C290.0507 (15)0.0458 (15)0.0447 (15)0.0185 (12)0.0055 (13)0.0116 (12)
C300.0614 (19)0.0623 (18)0.0586 (17)0.0276 (15)0.0073 (14)0.0220 (15)
C310.0504 (17)0.0607 (18)0.0686 (19)0.0126 (14)0.0064 (15)0.0169 (15)
C320.0577 (17)0.0413 (14)0.0444 (15)0.0194 (13)0.0098 (13)0.0104 (12)
C330.086 (2)0.0537 (17)0.0650 (19)0.0168 (16)0.0207 (17)0.0217 (15)
C340.114 (3)0.0609 (19)0.060 (2)0.036 (2)0.030 (2)0.0369 (16)
C350.105 (3)0.076 (2)0.062 (2)0.043 (2)0.0090 (18)0.0303 (17)
C360.072 (2)0.0658 (19)0.0578 (18)0.0257 (16)0.0009 (15)0.0180 (15)
C370.0544 (16)0.0411 (14)0.0395 (14)0.0206 (12)0.0021 (12)0.0111 (11)
C380.0579 (17)0.0432 (14)0.0488 (16)0.0176 (12)0.0097 (13)0.0125 (12)
C390.0640 (18)0.0391 (14)0.0416 (14)0.0259 (13)0.0164 (13)0.0151 (12)
C400.0511 (15)0.0372 (14)0.0368 (13)0.0152 (11)0.0069 (12)0.0149 (11)
C410.0410 (13)0.0364 (13)0.0303 (12)0.0118 (11)0.0002 (10)0.0086 (10)
C420.0454 (14)0.0341 (13)0.0330 (12)0.0153 (11)0.0085 (11)0.0115 (10)
C430.0485 (15)0.0407 (14)0.0386 (14)0.0143 (11)0.0097 (12)0.0158 (11)
C440.0443 (14)0.0432 (14)0.0312 (13)0.0147 (11)0.0052 (11)0.0117 (11)
C450.0515 (15)0.0475 (15)0.0375 (14)0.0212 (12)0.0078 (12)0.0081 (11)
C460.0481 (15)0.0458 (14)0.0355 (14)0.0143 (12)0.0039 (12)0.0060 (12)
C470.0462 (15)0.0423 (14)0.0463 (15)0.0168 (11)0.0061 (12)0.0188 (12)
C480.0582 (17)0.0429 (16)0.0646 (17)0.0188 (13)0.0005 (14)0.0131 (14)
C490.0590 (19)0.0391 (16)0.115 (3)0.0128 (13)0.0037 (18)0.0214 (17)
C500.069 (2)0.071 (2)0.117 (3)0.0235 (18)0.018 (2)0.063 (2)
C510.074 (2)0.087 (2)0.072 (2)0.0259 (18)0.0074 (17)0.0509 (19)
C520.0633 (18)0.0545 (16)0.0531 (17)0.0146 (14)0.0022 (14)0.0219 (14)
C530.0438 (15)0.0353 (13)0.0332 (13)0.0119 (11)0.0076 (11)0.0121 (10)
C540.0414 (14)0.0525 (15)0.0488 (15)0.0128 (12)0.0048 (13)0.0093 (13)
C550.0559 (17)0.0500 (15)0.0382 (14)0.0105 (13)0.0016 (13)0.0033 (12)
C560.0556 (17)0.0419 (14)0.0384 (14)0.0172 (12)0.0152 (13)0.0102 (12)
C570.0430 (16)0.079 (2)0.0510 (17)0.0196 (14)0.0053 (14)0.0048 (15)
C580.0479 (17)0.0681 (18)0.0380 (15)0.0143 (13)0.0021 (12)0.0016 (13)
F10.1202 (15)0.0762 (11)0.0562 (10)0.0345 (10)0.0334 (10)0.0087 (9)
F20.0802 (11)0.0779 (11)0.0503 (9)0.0310 (9)0.0238 (8)0.0049 (8)
N10.0551 (13)0.0349 (11)0.0331 (11)0.0134 (9)0.0049 (9)0.0099 (9)
N20.0507 (12)0.0346 (11)0.0310 (11)0.0141 (9)0.0063 (9)0.0112 (9)
N30.0518 (12)0.0355 (11)0.0366 (11)0.0123 (9)0.0088 (9)0.0120 (9)
N40.0884 (18)0.0704 (16)0.0422 (13)0.0212 (13)0.0010 (13)0.0186 (12)
N50.0531 (13)0.0403 (11)0.0334 (11)0.0188 (9)0.0093 (10)0.0141 (9)
N60.0506 (12)0.0379 (11)0.0330 (11)0.0172 (9)0.0100 (9)0.0130 (9)
N70.0557 (13)0.0379 (11)0.0382 (11)0.0184 (10)0.0088 (10)0.0137 (9)
N80.0809 (17)0.0674 (15)0.0411 (13)0.0101 (13)0.0171 (12)0.0155 (12)
O10.0797 (13)0.0349 (9)0.0416 (10)0.0162 (9)0.0006 (9)0.0129 (8)
O20.0777 (13)0.0433 (10)0.0414 (10)0.0175 (9)0.0042 (9)0.0167 (8)
O30.0910 (14)0.0457 (10)0.0494 (10)0.0374 (10)0.0275 (10)0.0240 (8)
O40.0870 (14)0.0508 (11)0.0529 (11)0.0271 (10)0.0350 (10)0.0267 (9)
Geometric parameters (Å, º) top
C1—C21.362 (3)C30—C311.352 (3)
C1—C101.396 (3)C30—C391.390 (3)
C1—H10.9300C30—H300.9300
C2—C31.407 (3)C31—C321.406 (3)
C2—H20.9300C31—H310.9300
C3—C41.412 (3)C32—C371.405 (3)
C3—C81.414 (3)C32—C331.428 (3)
C4—C51.358 (4)C33—C341.366 (4)
C4—H40.9300C33—H330.9300
C5—C61.387 (4)C34—C351.392 (4)
C5—H50.9300C34—H340.9300
C6—C71.371 (3)C35—C361.354 (4)
C6—H60.9300C35—H350.9300
C7—C81.411 (3)C36—C371.397 (3)
C7—H70.9300C36—H360.9300
C8—C91.420 (3)C37—C381.428 (3)
C9—C101.349 (3)C38—C391.351 (3)
C9—H90.9300C38—H380.9300
C10—O11.419 (2)C39—O31.413 (3)
C11—N11.286 (3)C40—N51.290 (3)
C11—O11.344 (2)C40—O31.338 (3)
C11—N21.378 (3)C40—N61.376 (3)
C12—O21.218 (2)C41—N51.372 (3)
C12—N21.427 (3)C41—C421.378 (3)
C12—C131.429 (3)C41—C441.419 (3)
C13—C141.382 (3)C42—N71.383 (3)
C13—N31.382 (3)C42—C431.432 (3)
C14—N11.374 (3)C43—O41.213 (2)
C14—C161.411 (3)C43—N61.425 (3)
C15—N31.361 (3)C44—C451.378 (3)
C15—C161.374 (3)C44—C461.425 (3)
C15—H150.9300C45—N71.361 (3)
C16—C171.427 (3)C45—H450.9300
C17—N41.142 (3)C46—N81.137 (3)
C18—C231.370 (3)C47—C481.376 (3)
C18—C191.371 (3)C47—C521.376 (3)
C18—N31.445 (3)C47—N71.443 (3)
C19—C201.378 (3)C48—C491.378 (3)
C19—H190.9300C48—H480.9300
C20—C211.368 (4)C49—C501.377 (4)
C20—H200.9300C49—H490.9300
C21—C221.367 (4)C50—C511.368 (4)
C21—H210.9300C50—H500.9300
C22—C231.377 (3)C51—C521.379 (3)
C22—H220.9300C51—H510.9300
C23—H230.9300C52—H520.9300
C24—C251.363 (3)C53—C581.363 (3)
C24—C291.382 (3)C53—C541.366 (3)
C24—N21.451 (3)C53—N61.455 (3)
C25—C261.385 (3)C54—C551.383 (3)
C25—H250.9300C54—H540.9300
C26—C271.366 (4)C55—C561.351 (3)
C26—H260.9300C55—H550.9300
C27—C281.352 (4)C56—C571.355 (3)
C27—F11.358 (3)C56—F21.365 (2)
C28—C291.380 (3)C57—C581.383 (3)
C28—H280.9300C57—H570.9300
C29—H290.9300C58—H580.9300
C2—C1—C10118.8 (2)C31—C32—C33122.1 (3)
C2—C1—H1120.6C34—C33—C32119.9 (3)
C10—C1—H1120.6C34—C33—H33120.0
C1—C2—C3121.4 (2)C32—C33—H33120.0
C1—C2—H2119.3C33—C34—C35120.2 (3)
C3—C2—H2119.3C33—C34—H34119.9
C2—C3—C4122.8 (2)C35—C34—H34119.9
C2—C3—C8118.9 (2)C36—C35—C34121.3 (3)
C4—C3—C8118.4 (2)C36—C35—H35119.4
C5—C4—C3120.9 (3)C34—C35—H35119.4
C5—C4—H4119.5C35—C36—C37120.1 (3)
C3—C4—H4119.5C35—C36—H36119.9
C4—C5—C6120.8 (3)C37—C36—H36119.9
C4—C5—H5119.6C36—C37—C32120.0 (2)
C6—C5—H5119.6C36—C37—C38121.2 (2)
C7—C6—C5120.3 (3)C32—C37—C38118.8 (2)
C7—C6—H6119.8C39—C38—C37119.0 (2)
C5—C6—H6119.8C39—C38—H38120.5
C6—C7—C8120.3 (3)C37—C38—H38120.5
C6—C7—H7119.8C38—C39—C30122.2 (2)
C8—C7—H7119.8C38—C39—O3119.6 (2)
C7—C8—C3119.2 (2)C30—C39—O3118.0 (2)
C7—C8—C9122.0 (2)N5—C40—O3122.2 (2)
C3—C8—C9118.8 (2)N5—C40—N6126.2 (2)
C10—C9—C8119.6 (2)O3—C40—N6111.60 (19)
C10—C9—H9120.2N5—C41—C42125.5 (2)
C8—C9—H9120.2N5—C41—C44127.5 (2)
C9—C10—C1122.5 (2)C42—C41—C44107.03 (19)
C9—C10—O1117.0 (2)C41—C42—N7108.81 (18)
C1—C10—O1120.3 (2)C41—C42—C43121.1 (2)
N1—C11—O1122.4 (2)N7—C42—C43129.97 (19)
N1—C11—N2126.2 (2)O4—C43—N6120.3 (2)
O1—C11—N2111.41 (19)O4—C43—C42129.0 (2)
O2—C12—N2120.1 (2)N6—C43—C42110.68 (18)
O2—C12—C13129.1 (2)C45—C44—C41106.64 (19)
N2—C12—C13110.78 (19)C45—C44—C46126.1 (2)
C14—C13—N3108.11 (19)C41—C44—C46127.2 (2)
C14—C13—C12121.3 (2)N7—C45—C44109.7 (2)
N3—C13—C12130.6 (2)N7—C45—H45125.1
N1—C14—C13125.1 (2)C44—C45—H45125.1
N1—C14—C16127.6 (2)N8—C46—C44179.8 (3)
C13—C14—C16107.3 (2)C48—C47—C52121.2 (2)
N3—C15—C16109.3 (2)C48—C47—N7118.9 (2)
N3—C15—H15125.3C52—C47—N7119.8 (2)
C16—C15—H15125.3C47—C48—C49119.4 (3)
C15—C16—C14106.97 (19)C47—C48—H48120.3
C15—C16—C17127.4 (2)C49—C48—H48120.3
C14—C16—C17125.7 (2)C50—C49—C48119.8 (3)
N4—C17—C16178.2 (3)C50—C49—H49120.1
C23—C18—C19120.9 (2)C48—C49—H49120.1
C23—C18—N3119.9 (2)C51—C50—C49120.3 (3)
C19—C18—N3119.2 (2)C51—C50—H50119.8
C18—C19—C20119.5 (2)C49—C50—H50119.8
C18—C19—H19120.2C50—C51—C52120.5 (3)
C20—C19—H19120.2C50—C51—H51119.7
C21—C20—C19119.8 (3)C52—C51—H51119.7
C21—C20—H20120.1C47—C52—C51118.8 (3)
C19—C20—H20120.1C47—C52—H52120.6
C22—C21—C20120.4 (3)C51—C52—H52120.6
C22—C21—H21119.8C58—C53—C54120.7 (2)
C20—C21—H21119.8C58—C53—N6120.2 (2)
C21—C22—C23120.2 (3)C54—C53—N6119.2 (2)
C21—C22—H22119.9C53—C54—C55120.1 (2)
C23—C22—H22119.9C53—C54—H54119.9
C18—C23—C22119.2 (2)C55—C54—H54119.9
C18—C23—H23120.4C56—C55—C54118.0 (2)
C22—C23—H23120.4C56—C55—H55121.0
C25—C24—C29120.8 (2)C54—C55—H55121.0
C25—C24—N2119.7 (2)C55—C56—C57123.2 (2)
C29—C24—N2119.5 (2)C55—C56—F2118.6 (2)
C24—C25—C26119.7 (2)C57—C56—F2118.2 (2)
C24—C25—H25120.2C56—C57—C58118.5 (2)
C26—C25—H25120.2C56—C57—H57120.8
C27—C26—C25118.4 (3)C58—C57—H57120.8
C27—C26—H26120.8C53—C58—C57119.6 (2)
C25—C26—H26120.8C53—C58—H58120.2
C28—C27—F1119.3 (3)C57—C58—H58120.2
C28—C27—C26122.9 (2)C11—N1—C14113.77 (18)
F1—C27—C26117.8 (3)C11—N2—C12122.77 (19)
C27—C28—C29118.7 (2)C11—N2—C24121.16 (18)
C27—C28—H28120.7C12—N2—C24116.04 (17)
C29—C28—H28120.7C15—N3—C13108.28 (18)
C28—C29—C24119.5 (2)C15—N3—C18123.98 (18)
C28—C29—H29120.2C13—N3—C18127.73 (19)
C24—C29—H29120.2C40—N5—C41113.49 (19)
C31—C30—C39120.0 (3)C40—N6—C43122.93 (18)
C31—C30—H30120.0C40—N6—C53120.83 (18)
C39—C30—H30120.0C43—N6—C53116.23 (17)
C30—C31—C32120.5 (3)C45—N7—C42107.81 (18)
C30—C31—H31119.7C45—N7—C47123.35 (19)
C32—C31—H31119.7C42—N7—C47128.84 (18)
C37—C32—C31119.5 (2)C11—O1—C10118.48 (17)
C37—C32—C33118.4 (2)C40—O3—C39118.28 (17)
C10—C1—C2—C31.5 (4)N5—C41—C44—C463.6 (4)
C1—C2—C3—C4179.2 (2)C42—C41—C44—C46178.0 (2)
C1—C2—C3—C80.8 (3)C41—C44—C45—N70.2 (3)
C2—C3—C4—C5179.6 (2)C46—C44—C45—N7178.1 (2)
C8—C3—C4—C50.4 (4)C45—C44—C46—N8160 (100)
C3—C4—C5—C60.0 (4)C41—C44—C46—N818 (100)
C4—C5—C6—C70.5 (4)C52—C47—C48—C490.1 (4)
C5—C6—C7—C80.6 (4)N7—C47—C48—C49179.2 (2)
C6—C7—C8—C30.1 (4)C47—C48—C49—C501.2 (4)
C6—C7—C8—C9180.0 (2)C48—C49—C50—C511.4 (5)
C2—C3—C8—C7179.6 (2)C49—C50—C51—C520.3 (5)
C4—C3—C8—C70.3 (3)C48—C47—C52—C511.3 (4)
C2—C3—C8—C90.5 (3)N7—C47—C52—C51179.7 (2)
C4—C3—C8—C9179.5 (2)C50—C51—C52—C471.1 (4)
C7—C8—C9—C10179.2 (2)C58—C53—C54—C551.0 (3)
C3—C8—C9—C100.9 (3)N6—C53—C54—C55179.4 (2)
C8—C9—C10—C10.1 (3)C53—C54—C55—C560.6 (3)
C8—C9—C10—O1174.77 (18)C54—C55—C56—C570.4 (4)
C2—C1—C10—C91.1 (4)C54—C55—C56—F2178.9 (2)
C2—C1—C10—O1175.8 (2)C55—C56—C57—C581.0 (4)
O2—C12—C13—C14177.5 (2)F2—C56—C57—C58178.3 (2)
N2—C12—C13—C143.2 (3)C54—C53—C58—C570.4 (4)
O2—C12—C13—N30.3 (4)N6—C53—C58—C57180.0 (2)
N2—C12—C13—N3179.0 (2)C56—C57—C58—C530.6 (4)
N3—C13—C14—N1179.70 (19)O1—C11—N1—C14179.8 (2)
C12—C13—C14—N11.5 (3)N2—C11—N1—C140.6 (3)
N3—C13—C14—C160.0 (2)C13—C14—N1—C110.6 (3)
C12—C13—C14—C16178.3 (2)C16—C14—N1—C11179.7 (2)
N3—C15—C16—C140.2 (3)N1—C11—N2—C121.6 (4)
N3—C15—C16—C17179.6 (2)O1—C11—N2—C12177.76 (18)
N1—C14—C16—C15179.8 (2)N1—C11—N2—C24179.6 (2)
C13—C14—C16—C150.1 (3)O1—C11—N2—C240.3 (3)
N1—C14—C16—C170.0 (4)O2—C12—N2—C11177.3 (2)
C13—C14—C16—C17179.7 (2)C13—C12—N2—C113.3 (3)
C15—C16—C17—N4172 (9)O2—C12—N2—C240.8 (3)
C14—C16—C17—N48 (9)C13—C12—N2—C24178.60 (18)
C23—C18—C19—C200.2 (4)C25—C24—N2—C1199.4 (3)
N3—C18—C19—C20180.0 (2)C29—C24—N2—C1182.0 (3)
C18—C19—C20—C210.5 (4)C25—C24—N2—C1278.7 (3)
C19—C20—C21—C220.1 (5)C29—C24—N2—C1299.9 (2)
C20—C21—C22—C231.1 (5)C16—C15—N3—C130.3 (3)
C19—C18—C23—C221.4 (4)C16—C15—N3—C18178.5 (2)
N3—C18—C23—C22178.9 (2)C14—C13—N3—C150.2 (2)
C21—C22—C23—C181.9 (4)C12—C13—N3—C15178.2 (2)
C29—C24—C25—C260.6 (4)C14—C13—N3—C18178.5 (2)
N2—C24—C25—C26178.0 (2)C12—C13—N3—C180.5 (4)
C24—C25—C26—C270.1 (4)C23—C18—N3—C15128.1 (2)
C25—C26—C27—C280.6 (4)C19—C18—N3—C1551.6 (3)
C25—C26—C27—F1179.8 (2)C23—C18—N3—C1353.4 (3)
F1—C27—C28—C29179.5 (2)C19—C18—N3—C13126.9 (2)
C26—C27—C28—C290.9 (4)O3—C40—N5—C41179.2 (2)
C27—C28—C29—C240.4 (3)N6—C40—N5—C411.1 (3)
C25—C24—C29—C280.3 (3)C42—C41—N5—C401.0 (3)
N2—C24—C29—C28178.30 (19)C44—C41—N5—C40179.2 (2)
C39—C30—C31—C320.4 (4)N5—C40—N6—C430.8 (4)
C30—C31—C32—C370.9 (4)O3—C40—N6—C43177.44 (19)
C30—C31—C32—C33179.1 (2)N5—C40—N6—C53178.4 (2)
C37—C32—C33—C340.1 (4)O3—C40—N6—C533.4 (3)
C31—C32—C33—C34178.2 (2)O4—C43—N6—C40177.5 (2)
C32—C33—C34—C350.3 (4)C42—C43—N6—C402.6 (3)
C33—C34—C35—C360.8 (4)O4—C43—N6—C533.3 (3)
C34—C35—C36—C370.8 (4)C42—C43—N6—C53176.62 (19)
C35—C36—C37—C320.4 (4)C58—C53—N6—C4089.2 (3)
C35—C36—C37—C38179.4 (2)C54—C53—N6—C4091.2 (3)
C31—C32—C37—C36178.3 (2)C58—C53—N6—C4391.6 (3)
C33—C32—C37—C360.1 (3)C54—C53—N6—C4388.0 (2)
C31—C32—C37—C381.5 (3)C44—C45—N7—C420.0 (3)
C33—C32—C37—C38179.9 (2)C44—C45—N7—C47179.8 (2)
C36—C37—C38—C39178.8 (2)C41—C42—N7—C450.2 (2)
C32—C37—C38—C391.0 (3)C43—C42—N7—C45177.0 (2)
C37—C38—C39—C300.3 (4)C41—C42—N7—C47179.6 (2)
C37—C38—C39—O3174.76 (18)C43—C42—N7—C472.8 (4)
C31—C30—C39—C381.0 (4)C48—C47—N7—C4547.9 (3)
C31—C30—C39—O3175.6 (2)C52—C47—N7—C45131.1 (2)
N5—C41—C42—N7178.1 (2)C48—C47—N7—C42131.9 (2)
C44—C41—C42—N70.3 (2)C52—C47—N7—C4249.1 (3)
N5—C41—C42—C431.0 (3)N1—C11—O1—C100.5 (3)
C44—C41—C42—C43177.5 (2)N2—C11—O1—C10179.88 (19)
C41—C42—C43—O4177.5 (2)C9—C10—O1—C11121.3 (2)
N7—C42—C43—O41.0 (4)C1—C10—O1—C1163.7 (3)
C41—C42—C43—N62.6 (3)N5—C40—O3—C392.5 (3)
N7—C42—C43—N6179.1 (2)N6—C40—O3—C39179.12 (19)
N5—C41—C44—C45178.1 (2)C38—C39—O3—C40100.2 (3)
C42—C41—C44—C450.3 (2)C30—C39—O3—C4085.1 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C45—H45···N4i0.932.483.312 (3)150
C15—H15···N8ii0.932.483.294 (3)147
Symmetry codes: (i) x, y+1, z; (ii) x, y1, z.

Experimental details

Crystal data
Chemical formulaC29H17FN4O2
Mr472.47
Crystal system, space groupTriclinic, P1
Temperature (K)298
a, b, c (Å)9.8522 (16), 14.549 (2), 16.792 (3)
α, β, γ (°)101.755 (3), 90.840 (3), 103.789 (3)
V3)2283.5 (6)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.16 × 0.12 × 0.10
Data collection
DiffractometerBruker SMART CCD area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 2001)
Tmin, Tmax0.985, 0.991
No. of measured, independent and
observed [I > 2σ(I)] reflections
14836, 8839, 5302
Rint0.082
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.056, 0.129, 0.93
No. of reflections8839
No. of parameters649
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.22, 0.20

Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C45—H45···N4i0.932.483.312 (3)149.6
C15—H15···N8ii0.932.483.294 (3)146.7
Symmetry codes: (i) x, y+1, z; (ii) x, y1, z.
 

Acknowledgements

We gratefully acknowledge financial support of this work by the Key Science Research Project of the Hubei Provincial Department of Education (No. D200724001) and the Science Research Project of Yunyang Medical College (No. 2006QDJ16)

References

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