PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2008 September 1; 64(Pt 9): o1680.
Published online 2008 August 6. doi:  10.1107/S1600536808024410
PMCID: PMC2960589

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

Abstract

There are two crystallographically independent mol­ecules in the asymmetric unit of the title compound, C26H17FN4O3, which differ in the dihedral angles between the aromatic rings (fluorophenyl, phenyl) and the pyrrolopyrimidine rings [0.6 (3)/76.3° and 73.7 (3)/64.6°, respectively]. The crystal structure is mainly stabilized by C—H(...)O and C—H(...)F inter­actions.

Related literature

For related preparation and biological activity, see: Shih et al. (2002 [triangle]); Niwas et al. (1994 [triangle]). For related literature, see: Ding et al. (2004 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o1680-scheme1.jpg

Experimental

Crystal data

  • C26H17FN4O3
  • M r = 452.44
  • Tetragonal, An external file that holds a picture, illustration, etc.
Object name is e-64-o1680-efi1.jpg
  • a = 17.7893 (14) Å
  • c = 14.332 (12) Å
  • V = 4536 (1) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 298 (2) K
  • 0.36 × 0.23 × 0.20 mm

Data collection

  • Bruker SMART 4K CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 2003 [triangle]) T min = 0.967, T max = 0.981
  • 29534 measured reflections
  • 4649 independent reflections
  • 2383 reflections with I > 2σ(I)
  • R int = 0.136

Refinement

  • R[F 2 > 2σ(F 2)] = 0.054
  • wR(F 2) = 0.087
  • S = 0.89
  • 4649 reflections
  • 615 parameters
  • H-atom parameters constrained
  • Δρmax = 0.18 e Å−3
  • Δρmin = −0.13 e Å−3

Data collection: SMART (Bruker, 2001 [triangle]); cell refinement: SAINT-Plus (Bruker, 2001 [triangle]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: PLATON (Spek, 2003 [triangle]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808024410/bt2753sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808024410/bt2753Isup2.hkl

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

Acknowledgments

We gratefully acknowledge financial support of this work by the Key Science Research Project of Hubei Provincial Department of Education (No. D200724002).

supplementary crystallographic information

Comment

Heterocyclic compounds containing a fused pyrimidinone system have various applications in agriculture and exhibit remarkable biological activity (Ding et al., 2004). Pyrrolopyrimidine derivatives are of great importance because of their remarkable biological properties (Shih, et al., 2002; Niwas, et al., 1994). We present here the crystal structure of the title compound, (Fig. 1), which can be used as a precursor for obtaining bioactive molecules. Within the molecule of the title compound, the bond lengths and angles present no unusual features. In the crystal stucture, two crystallographically independent molecules are found in the asymmetric unit. The mean planes of the pyrrolo[3,2-d]pyrimidine ring system [maximum deviation of 0.028 (4)Å and -0.044 Å for atom C31 and C28, respectively] (A), and the fluorophenyl (B) and phenyl (C12–17 and C35–40) rings (C) form dihedral angles of A/B=80.6 (3)/76.3° and A/C=73.7 (3)/64.6°, respectively. The crystal packing is mainly stabilized by C—H···O and C—H···F interactions (Table 1, Fig.2).

Experimental

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

All H-atoms were positioned geometrically and refined using a riding model with C—H = 0.93 Å, Uiso = 1.2Ueq (C) for Csp2, C—H = 0.96 Å, Uiso = 1.5Ueq (C) for CH3. The methyl groups were allowed to rotate but not to tip.

Figures

Fig. 1.
The molecular structure of the two molecules of title compound, showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 50% probability level.

Crystal data

C26H17FN4O3Dx = 1.325 Mg m3
Mr = 452.44Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P4Cell parameters from 1922 reflections
Hall symbol: P -4θ = 2.7–15.1°
a = 17.7893 (14) ŵ = 0.10 mm1
c = 14.332 (12) ÅT = 298 K
V = 4536 (1) Å3Block, colorless
Z = 80.36 × 0.23 × 0.20 mm
F(000) = 1872

Data collection

Bruker SMART 4K CCD area-detector diffractometer4649 independent reflections
Radiation source: fine-focus sealed tube2383 reflections with I > 2σ(I)
graphiteRint = 0.136
[var phi] and ω scansθmax = 26.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)h = −21→21
Tmin = 0.967, Tmax = 0.981k = −14→21
29534 measured reflectionsl = −15→17

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)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.087H-atom parameters constrained
S = 0.89w = 1/[σ2(Fo2) + (0.0193P)2] where P = (Fo2 + 2Fc2)/3
4649 reflections(Δ/σ)max = 0.001
615 parametersΔρmax = 0.18 e Å3
0 restraintsΔρmin = −0.13 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
C310.6200 (3)0.3475 (2)1.0850 (3)0.0412 (12)
O20.66811 (18)0.3679 (2)1.3288 (3)0.0630 (11)
N70.7396 (2)0.3638 (2)1.1952 (3)0.0412 (10)
C280.7437 (3)0.3632 (3)1.0988 (4)0.0444 (13)
N90.5317 (2)0.3477 (2)1.1964 (3)0.0477 (11)
N80.6890 (2)0.3529 (2)1.0423 (3)0.0420 (10)
N41.0211 (2)0.2597 (2)0.7835 (3)0.0494 (11)
O30.81483 (18)0.37435 (19)1.0689 (2)0.0553 (10)
O41.06797 (19)0.33069 (19)0.8982 (2)0.0640 (11)
O10.9751 (2)0.1919 (2)0.6606 (3)0.0789 (13)
C340.5346 (3)0.3317 (3)0.9458 (4)0.0581 (16)
N100.5252 (2)0.3231 (3)0.8671 (4)0.0746 (15)
C260.8505 (3)0.4065 (4)0.7843 (4)0.0609 (16)
C51.0216 (3)0.2733 (3)0.8782 (4)0.0512 (14)
N50.8849 (2)0.1032 (2)0.8045 (3)0.0567 (12)
C60.9765 (3)0.2016 (3)0.7437 (4)0.0544 (15)
C110.8746 (3)0.1359 (3)1.0535 (5)0.0606 (17)
C240.8248 (3)0.3848 (3)0.9715 (4)0.0491 (14)
C70.9358 (3)0.1621 (3)0.8147 (4)0.0501 (14)
C11.0898 (3)0.3401 (3)0.9930 (4)0.0514 (14)
C250.8316 (3)0.3370 (3)0.8180 (4)0.0604 (16)
H250.82690.29670.77690.073*
N30.9855 (2)0.2373 (2)0.9408 (3)0.0471 (11)
C330.5488 (3)0.3395 (3)1.0413 (3)0.0454 (13)
C300.6091 (3)0.3514 (2)1.1806 (3)0.0413 (13)
C290.6700 (3)0.3619 (3)1.2437 (4)0.0460 (13)
C550.8445 (3)0.4541 (3)0.9404 (4)0.0648 (16)
H550.84880.49390.98210.078*
O51.1558 (3)0.3706 (2)1.2655 (3)0.0924 (14)
O60.8632 (2)0.4231 (2)0.6920 (3)0.0884 (13)
C400.4465 (3)0.4174 (3)1.2950 (4)0.0758 (18)
H400.44090.45201.24690.091*
F20.98805 (19)0.4048 (2)1.4194 (3)0.1178 (15)
C181.0680 (3)0.3002 (3)0.7195 (4)0.0556 (15)
N60.8625 (3)0.1418 (3)1.1308 (4)0.097 (2)
C320.4970 (3)0.3405 (3)1.1138 (4)0.0556 (15)
H320.44520.33671.10610.067*
C120.8670 (3)0.0632 (3)0.7187 (4)0.0537 (14)
C410.8059 (3)0.3745 (3)1.2517 (3)0.0452 (13)
C350.4932 (3)0.3573 (3)1.2841 (4)0.0471 (14)
C31.1378 (4)0.3599 (3)1.1729 (5)0.0660 (17)
C100.8910 (3)0.1325 (3)0.9557 (4)0.0518 (14)
C130.8993 (4)−0.0050 (4)0.7072 (5)0.091 (2)
H130.9283−0.02600.75450.109*
C160.8110 (4)0.0538 (5)0.5674 (5)0.100 (2)
H160.78030.07290.52050.120*
C80.9412 (3)0.1813 (3)0.9075 (3)0.0481 (14)
C521.1609 (3)0.3226 (3)1.0168 (4)0.0602 (16)
H521.19330.30280.97230.072*
C450.9151 (3)0.3271 (4)1.3238 (5)0.088 (2)
H450.94780.28741.33560.106*
C191.0473 (4)0.3678 (3)0.6846 (4)0.0735 (18)
H191.00360.39030.70680.088*
F11.1930 (2)0.4033 (3)0.5191 (2)0.1469 (19)
C360.5012 (3)0.3064 (3)1.3546 (4)0.0623 (16)
H360.53300.26531.34760.075*
C90.8584 (3)0.0860 (3)0.8900 (4)0.0588 (16)
H90.82340.04860.90290.071*
C380.4152 (3)0.3771 (4)1.4479 (5)0.080 (2)
H380.38910.38421.50340.096*
C390.4081 (3)0.4267 (4)1.3765 (5)0.090 (2)
H390.37630.46781.38330.108*
C460.8541 (3)0.3167 (3)1.2673 (4)0.0652 (17)
H460.84560.27021.23970.078*
C430.8836 (4)0.4536 (4)1.3457 (4)0.081 (2)
H430.89420.50041.37150.098*
C540.8196 (3)0.3259 (3)0.9119 (4)0.0557 (15)
H540.80790.27830.93440.067*
C211.1513 (5)0.3700 (5)0.5884 (5)0.094 (3)
C41.1859 (3)0.3338 (3)1.1067 (5)0.0657 (17)
H41.23560.32361.12210.079*
C420.8206 (3)0.4439 (3)1.2886 (4)0.0717 (18)
H420.78900.48431.27570.086*
C170.8225 (4)0.0940 (4)0.6520 (5)0.092 (2)
H170.79990.14060.66130.111*
C370.4615 (3)0.3164 (4)1.4366 (4)0.0707 (17)
H370.46640.28161.48460.085*
C440.9278 (3)0.3955 (5)1.3627 (4)0.076 (2)
C270.8582 (3)0.4651 (4)0.8466 (5)0.0771 (19)
H270.87270.51230.82530.093*
C231.1331 (4)0.2674 (4)0.6902 (4)0.086 (2)
H231.14850.22170.71520.103*
C150.8461 (5)−0.0133 (5)0.5573 (6)0.106 (3)
H150.8401−0.03950.50160.127*
C21.0653 (4)0.3787 (4)1.1482 (5)0.084 (2)
H21.03300.39821.19300.101*
C221.1767 (4)0.3036 (5)0.6216 (5)0.106 (3)
H221.22130.28260.59990.128*
C531.0402 (3)0.3691 (3)1.0587 (5)0.0789 (18)
H530.99120.38171.04230.095*
C140.8885 (5)−0.0432 (5)0.6237 (6)0.121 (3)
H140.9112−0.08970.61440.145*
C201.0880 (5)0.4040 (4)0.6183 (5)0.096 (2)
H201.07290.45020.59450.115*
C510.8501 (4)0.3657 (4)0.6251 (5)0.106 (2)
H51A0.88330.32420.63690.159*
H51B0.85930.38510.56360.159*
H51C0.79890.34900.62950.159*
C501.2292 (4)0.3516 (4)1.2947 (4)0.112 (3)
H50A1.23660.29841.28800.168*
H50B1.23570.36551.35890.168*
H50C1.26520.37791.25700.168*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C310.042 (3)0.046 (3)0.035 (3)−0.001 (2)0.004 (3)−0.002 (3)
O20.053 (2)0.093 (3)0.042 (3)−0.005 (2)−0.0041 (19)−0.003 (2)
N70.037 (3)0.052 (3)0.034 (3)−0.003 (2)0.000 (2)−0.002 (2)
C280.046 (4)0.044 (3)0.043 (4)−0.001 (3)0.002 (3)0.003 (3)
N90.044 (3)0.067 (3)0.032 (3)0.002 (2)0.000 (2)−0.003 (2)
N80.039 (3)0.043 (2)0.044 (3)0.001 (2)−0.003 (2)−0.004 (2)
N40.046 (3)0.062 (3)0.041 (3)−0.009 (2)0.002 (2)0.008 (2)
O30.036 (2)0.081 (3)0.049 (3)−0.0028 (18)−0.0016 (18)0.004 (2)
O40.069 (3)0.069 (3)0.054 (3)−0.028 (2)−0.005 (2)0.006 (2)
O10.094 (3)0.103 (3)0.039 (2)−0.033 (2)0.008 (2)0.001 (2)
C340.041 (3)0.088 (5)0.046 (4)−0.007 (3)−0.004 (3)−0.007 (4)
N100.056 (3)0.106 (4)0.062 (4)−0.012 (3)0.001 (3)−0.005 (3)
C260.048 (4)0.071 (5)0.064 (5)0.010 (3)0.018 (3)0.015 (4)
C50.044 (3)0.057 (4)0.053 (4)−0.004 (3)−0.003 (3)0.002 (3)
N50.067 (3)0.054 (3)0.049 (3)−0.007 (2)0.005 (3)−0.003 (3)
C60.054 (4)0.060 (4)0.049 (4)−0.002 (3)−0.005 (3)0.004 (3)
C110.067 (4)0.056 (4)0.058 (4)−0.022 (3)0.015 (4)−0.010 (3)
C240.038 (3)0.055 (4)0.054 (4)0.004 (3)0.006 (3)0.012 (3)
C70.051 (3)0.054 (4)0.045 (4)−0.009 (3)0.006 (3)0.009 (3)
C10.045 (4)0.058 (4)0.051 (4)−0.010 (3)0.010 (3)0.003 (3)
C250.054 (4)0.068 (4)0.059 (4)0.012 (3)0.005 (3)−0.006 (4)
N30.044 (3)0.050 (3)0.048 (3)−0.009 (2)0.001 (2)0.001 (2)
C330.042 (3)0.063 (4)0.031 (3)−0.006 (3)0.001 (3)−0.004 (3)
C300.040 (3)0.043 (3)0.040 (4)0.001 (3)−0.002 (3)0.002 (3)
C290.044 (4)0.055 (4)0.039 (4)0.000 (3)−0.007 (3)−0.004 (3)
C550.068 (4)0.067 (4)0.059 (4)−0.009 (3)0.013 (3)0.002 (3)
O50.108 (4)0.105 (4)0.064 (3)−0.018 (3)−0.002 (3)−0.024 (3)
O60.093 (3)0.108 (4)0.064 (3)0.006 (3)0.024 (3)0.027 (3)
C400.085 (5)0.096 (5)0.046 (4)0.015 (4)0.005 (4)0.004 (4)
F20.081 (3)0.168 (4)0.104 (3)−0.031 (3)−0.054 (2)0.022 (3)
C180.049 (4)0.072 (4)0.046 (4)−0.012 (3)−0.010 (3)0.010 (3)
N60.112 (5)0.122 (5)0.057 (4)−0.044 (4)0.024 (4)−0.014 (4)
C320.046 (4)0.062 (4)0.058 (4)−0.005 (3)−0.007 (3)−0.004 (3)
C120.051 (4)0.063 (4)0.047 (4)−0.009 (3)0.009 (3)−0.009 (3)
C410.040 (3)0.050 (3)0.045 (3)0.005 (3)−0.007 (3)0.003 (3)
C350.039 (3)0.064 (4)0.038 (4)0.002 (3)0.002 (3)−0.004 (3)
C30.070 (5)0.059 (4)0.069 (5)−0.018 (3)0.009 (4)−0.014 (4)
C100.060 (4)0.048 (4)0.047 (4)−0.011 (3)0.011 (3)−0.004 (3)
C130.114 (6)0.094 (5)0.065 (5)0.015 (5)−0.019 (4)−0.025 (4)
C160.107 (6)0.127 (7)0.064 (6)−0.033 (6)−0.026 (5)0.040 (6)
C80.047 (3)0.064 (4)0.034 (3)0.004 (3)0.008 (3)−0.002 (3)
C520.064 (4)0.063 (4)0.054 (4)−0.007 (3)0.003 (3)−0.006 (3)
C450.066 (5)0.095 (6)0.104 (6)0.008 (4)−0.036 (4)0.030 (5)
C190.083 (5)0.072 (4)0.065 (4)−0.023 (4)−0.008 (4)0.017 (4)
F10.172 (4)0.208 (5)0.061 (3)−0.120 (4)0.008 (3)0.020 (3)
C360.072 (4)0.068 (4)0.047 (4)0.006 (3)0.005 (3)−0.005 (3)
C90.072 (4)0.059 (4)0.046 (4)−0.010 (3)0.021 (3)0.008 (3)
C380.066 (5)0.120 (6)0.053 (5)−0.011 (4)0.015 (4)−0.019 (5)
C390.086 (5)0.123 (6)0.060 (5)0.025 (4)0.013 (4)−0.012 (5)
C460.068 (4)0.053 (4)0.074 (4)0.003 (3)−0.024 (4)0.003 (3)
C430.087 (5)0.077 (5)0.080 (5)−0.016 (4)−0.021 (4)−0.018 (4)
C540.051 (4)0.052 (4)0.064 (4)0.006 (3)−0.003 (3)0.005 (3)
C210.087 (6)0.151 (8)0.045 (5)−0.077 (6)0.003 (4)0.019 (5)
C40.058 (4)0.062 (4)0.077 (5)−0.001 (3)−0.005 (4)−0.007 (4)
C420.068 (4)0.062 (4)0.086 (5)0.003 (3)−0.025 (4)−0.020 (4)
C170.115 (6)0.079 (5)0.082 (5)−0.008 (4)−0.030 (5)0.020 (4)
C370.080 (5)0.080 (5)0.052 (4)−0.010 (4)0.009 (4)0.007 (4)
C440.053 (4)0.109 (6)0.065 (5)−0.023 (4)−0.023 (4)0.013 (5)
C270.088 (5)0.061 (4)0.082 (5)−0.010 (4)0.019 (4)0.014 (4)
C230.072 (5)0.116 (6)0.070 (5)0.002 (4)0.020 (4)0.025 (4)
C150.113 (7)0.145 (9)0.058 (5)−0.034 (6)0.014 (5)0.001 (6)
C20.088 (6)0.102 (5)0.062 (5)−0.006 (4)0.022 (4)−0.015 (4)
C220.068 (5)0.181 (9)0.070 (6)−0.018 (5)0.012 (4)0.020 (6)
C530.048 (4)0.095 (5)0.094 (5)0.003 (3)0.010 (4)−0.007 (4)
C140.149 (8)0.118 (7)0.095 (7)0.020 (6)−0.014 (6)−0.047 (6)
C200.111 (6)0.085 (5)0.091 (6)−0.044 (5)−0.012 (5)0.030 (5)
C510.124 (6)0.133 (7)0.062 (5)0.027 (5)0.006 (5)−0.005 (5)
C500.145 (7)0.126 (6)0.066 (5)−0.010 (6)−0.023 (5)−0.004 (5)

Geometric parameters (Å, °)

C31—N81.374 (5)C41—C461.356 (6)
C31—C301.386 (6)C41—C421.369 (7)
C31—C331.420 (6)C35—C361.365 (7)
O2—C291.225 (5)C3—C41.359 (7)
N7—C281.384 (6)C3—C21.379 (8)
N7—C291.420 (6)C10—C91.381 (7)
N7—C411.444 (6)C10—C81.423 (6)
C28—N81.279 (5)C13—C141.389 (8)
C28—O31.351 (5)C13—H130.9300
N9—C321.341 (6)C16—C151.355 (9)
N9—C301.396 (5)C16—C171.422 (9)
N9—C351.443 (6)C16—H160.9300
N4—C51.379 (6)C52—C41.378 (7)
N4—C61.422 (6)C52—H520.9300
N4—C181.433 (6)C45—C441.357 (8)
O3—C241.420 (6)C45—C461.367 (7)
O4—C51.344 (5)C45—H450.9300
O4—C11.422 (6)C19—C201.358 (8)
O4—C554.581 (6)C19—H190.9300
O1—C61.204 (6)F1—C211.374 (7)
C34—N101.150 (6)C36—C371.382 (7)
C34—C331.398 (7)C36—H360.9300
C26—C251.369 (7)C9—H90.9300
C26—O61.375 (6)C38—C391.357 (8)
C26—C271.379 (7)C38—C371.367 (7)
C5—N31.275 (6)C38—H380.9300
N5—C91.348 (6)C39—H390.9300
N5—C71.393 (6)C46—H460.9300
N5—C121.455 (6)C43—C441.322 (8)
C6—C71.433 (7)C43—C421.398 (7)
C11—N61.135 (6)C43—H430.9300
C11—C101.433 (7)C54—H540.9300
C24—C541.354 (7)C21—C221.352 (10)
C24—C551.357 (7)C21—C201.347 (10)
C7—C81.377 (6)C4—H40.9300
C1—C521.347 (7)C42—H420.9300
C1—C531.390 (7)C17—H170.9300
C25—C541.378 (7)C37—H370.9300
C25—H250.9300C27—H270.9300
N3—C81.358 (6)C23—C221.409 (8)
C33—C321.389 (6)C23—H230.9300
C30—C291.424 (6)C15—C141.327 (9)
C55—C271.381 (7)C15—H150.9300
C55—H550.9300C2—C531.370 (8)
O5—C31.378 (7)C2—H20.9300
O5—C501.412 (7)C22—H220.9300
O6—C511.419 (6)C53—H530.9300
C40—C351.362 (7)C14—H140.9300
C40—C391.363 (7)C20—H200.9300
C40—H400.9300C51—H51A0.9600
F2—C441.356 (6)C51—H51B0.9600
C18—C191.354 (7)C51—H51C0.9600
C18—C231.363 (7)C50—H50A0.9600
C32—H320.9300C50—H50B0.9600
C12—C131.353 (7)C50—H50C0.9600
C12—C171.358 (7)
N8—C31—C30124.2 (5)C15—C16—C17117.9 (8)
N8—C31—C33127.4 (4)C15—C16—H16121.1
C30—C31—C33108.4 (4)C17—C16—H16121.0
C28—N7—C29122.3 (4)N3—C8—C7124.2 (5)
C28—N7—C41121.2 (4)N3—C8—C10129.9 (5)
C29—N7—C41116.2 (4)C7—C8—C10105.9 (5)
N8—C28—O3122.2 (5)C1—C52—C4120.5 (5)
N8—C28—N7126.4 (5)C1—C52—H52119.7
O3—C28—N7111.4 (5)C4—C52—H52119.7
C32—N9—C30108.4 (4)C44—C45—C46119.7 (6)
C32—N9—C35124.2 (4)C44—C45—H45120.2
C30—N9—C35127.2 (4)C46—C45—H45120.1
C28—N8—C31114.0 (4)C18—C19—C20122.4 (7)
C5—N4—C6121.7 (5)C18—C19—H19118.8
C5—N4—C18122.5 (5)C20—C19—H19118.8
C6—N4—C18115.7 (4)C35—C36—C37119.4 (5)
C28—O3—C24116.6 (4)C35—C36—H36120.3
C5—O4—C1117.4 (4)C37—C36—H36120.3
C5—O4—C5582.0 (3)N5—C9—C10109.7 (5)
C1—O4—C5593.1 (3)N5—C9—H9125.1
N10—C34—C33177.2 (7)C10—C9—H9125.1
C25—C26—O6125.0 (6)C39—C38—C37118.7 (6)
C25—C26—C27118.6 (6)C39—C38—H38120.6
O6—C26—C27116.4 (6)C37—C38—H38120.6
N3—C5—O4122.7 (5)C38—C39—C40121.3 (6)
N3—C5—N4126.9 (5)C38—C39—H39119.4
O4—C5—N4110.4 (5)C40—C39—H39119.3
C9—N5—C7107.6 (5)C41—C46—C45119.8 (6)
C9—N5—C12125.6 (5)C41—C46—H46120.1
C7—N5—C12126.7 (5)C45—C46—H46120.1
O1—C6—N4120.8 (5)C44—C43—C42119.2 (6)
O1—C6—C7128.5 (5)C44—C43—H43120.4
N4—C6—C7110.7 (5)C42—C43—H43120.4
N6—C11—C10177.0 (7)C24—C54—C25119.7 (6)
C54—C24—C55120.9 (6)C24—C54—H54120.2
C54—C24—O3120.7 (5)C25—C54—H54120.2
C55—C24—O3118.3 (5)C22—C21—C20124.1 (7)
C8—C7—N5109.4 (5)C22—C21—F1116.8 (9)
C8—C7—C6122.0 (5)C20—C21—F1119.2 (9)
N5—C7—C6128.5 (5)C3—C4—C52119.9 (6)
C52—C1—C53120.7 (6)C3—C4—H4120.0
C52—C1—O4118.1 (5)C52—C4—H4120.0
C53—C1—O4121.2 (6)C41—C42—C43119.4 (6)
C26—C25—C54120.7 (6)C41—C42—H42120.3
C26—C25—H25119.6C43—C42—H42120.3
C54—C25—H25119.6C12—C17—C16118.8 (7)
C5—N3—C8114.4 (5)C12—C17—H17120.6
C32—C33—C34127.8 (5)C16—C17—H17120.6
C32—C33—C31105.1 (4)C38—C37—C36120.7 (6)
C34—C33—C31127.0 (5)C38—C37—H37119.7
C31—C30—N9107.2 (4)C36—C37—H37119.7
C31—C30—C29121.9 (5)C43—C44—F2119.0 (7)
N9—C30—C29130.8 (5)C43—C44—C45121.8 (6)
O2—C29—C30128.5 (5)F2—C44—C45119.1 (7)
O2—C29—N7120.6 (5)C26—C27—C55120.4 (6)
C30—C29—N7110.8 (4)C26—C27—H27119.8
C24—C55—C27119.6 (6)C55—C27—H27119.8
C24—C55—O480.3 (3)C18—C23—C22119.2 (7)
C27—C55—O477.6 (4)C18—C23—H23120.4
C24—C55—H55120.2C22—C23—H23120.4
C27—C55—H55120.2C14—C15—C16122.5 (9)
O4—C55—H55112.3C14—C15—H15118.8
C3—O5—C50117.8 (5)C16—C15—H15118.7
C26—O6—C51117.9 (5)C53—C2—C3121.1 (6)
C35—C40—C39120.0 (6)C53—C2—H2119.4
C35—C40—H40120.0C3—C2—H2119.4
C39—C40—H40120.0C21—C22—C23117.4 (7)
C19—C18—C23119.8 (6)C21—C22—H22121.3
C19—C18—N4121.7 (6)C23—C22—H22121.3
C23—C18—N4118.4 (5)C2—C53—C1118.2 (6)
N9—C32—C33110.8 (4)C2—C53—H53120.9
N9—C32—H32124.6C1—C53—H53120.9
C33—C32—H32124.6C15—C14—C13120.1 (8)
C13—C12—C17121.6 (6)C15—C14—H14119.9
C13—C12—N5116.7 (6)C13—C14—H14120.0
C17—C12—N5121.7 (6)C21—C20—C19117.1 (7)
C46—C41—C42120.0 (5)C21—C20—H20121.4
C46—C41—N7120.6 (5)C19—C20—H20121.4
C42—C41—N7119.4 (5)O6—C51—H51A109.5
C40—C35—C36119.9 (5)O6—C51—H51B109.5
C40—C35—N9118.9 (5)H51A—C51—H51B109.5
C36—C35—N9121.1 (5)O6—C51—H51C109.5
C4—C3—C2119.5 (6)H51A—C51—H51C109.5
C4—C3—O5125.0 (7)H51B—C51—H51C109.5
C2—C3—O5115.5 (6)O5—C50—H50A109.5
C9—C10—C8107.3 (5)O5—C50—H50B109.5
C9—C10—C11127.3 (5)H50A—C50—H50B109.5
C8—C10—C11125.2 (5)O5—C50—H50C109.5
C12—C13—C14119.0 (7)H50A—C50—H50C109.5
C12—C13—H13120.5H50B—C50—H50C109.5
C14—C13—H13120.5
C29—N7—C28—N8−8.1 (8)C7—N5—C12—C13101.5 (7)
C41—N7—C28—N8178.7 (5)C9—N5—C12—C17108.7 (7)
C29—N7—C28—O3172.7 (4)C7—N5—C12—C17−76.0 (8)
C41—N7—C28—O3−0.6 (6)C28—N7—C41—C46−79.3 (6)
O3—C28—N8—C31−176.0 (4)C29—N7—C41—C46107.1 (5)
N7—C28—N8—C314.8 (7)C28—N7—C41—C4299.9 (6)
C30—C31—N8—C28−0.9 (7)C29—N7—C41—C42−73.8 (6)
C33—C31—N8—C28176.9 (5)C39—C40—C35—C360.2 (9)
N8—C28—O3—C248.7 (7)C39—C40—C35—N9178.4 (5)
N7—C28—O3—C24−172.0 (4)C32—N9—C35—C40−58.7 (7)
C1—O4—C5—N314.3 (7)C30—N9—C35—C40114.5 (6)
C55—O4—C5—N3−75.1 (5)C32—N9—C35—C36119.4 (6)
C1—O4—C5—N4−164.6 (4)C30—N9—C35—C36−67.4 (7)
C55—O4—C5—N4106.0 (4)C50—O5—C3—C4−1.5 (9)
C6—N4—C5—N31.1 (8)C50—O5—C3—C2179.5 (6)
C18—N4—C5—N3−175.5 (5)C17—C12—C13—C142.2 (10)
C6—N4—C5—O4179.9 (4)N5—C12—C13—C14−175.4 (6)
C18—N4—C5—O43.3 (7)C5—N3—C8—C71.7 (7)
C5—N4—C6—O1177.9 (5)C5—N3—C8—C10−176.8 (5)
C18—N4—C6—O1−5.2 (8)N5—C7—C8—N3−179.2 (4)
C5—N4—C6—C7−0.5 (7)C6—C7—C8—N3−1.3 (8)
C18—N4—C6—C7176.3 (4)N5—C7—C8—C10−0.5 (6)
C28—O3—C24—C54−74.4 (6)C6—C7—C8—C10177.5 (5)
C28—O3—C24—C55109.8 (5)C9—C10—C8—N3179.1 (5)
C9—N5—C7—C80.3 (6)C11—C10—C8—N33.0 (9)
C12—N5—C7—C8−175.6 (5)C9—C10—C8—C70.5 (6)
C9—N5—C7—C6−177.5 (5)C11—C10—C8—C7−175.7 (5)
C12—N5—C7—C66.6 (9)C53—C1—C52—C4−0.6 (8)
O1—C6—C7—C8−177.6 (6)O4—C1—C52—C4177.1 (5)
N4—C6—C7—C80.6 (7)C23—C18—C19—C202.2 (9)
O1—C6—C7—N5−0.2 (10)N4—C18—C19—C20−174.4 (5)
N4—C6—C7—N5178.1 (5)C40—C35—C36—C370.0 (8)
C5—O4—C1—C52107.7 (5)N9—C35—C36—C37−178.1 (5)
C55—O4—C1—C52−169.8 (4)C12—N5—C9—C10176.0 (5)
C5—O4—C1—C53−74.7 (6)C8—C10—C9—N5−0.3 (6)
C55—O4—C1—C537.9 (5)C11—C10—C9—N5175.7 (5)
O6—C26—C25—C54−179.6 (5)C37—C38—C39—C40−0.6 (10)
C27—C26—C25—C540.8 (8)C42—C41—C46—C453.3 (9)
O4—C5—N3—C8179.7 (4)N7—C41—C46—C45−177.5 (5)
N4—C5—N3—C8−1.6 (8)C44—C45—C46—C41−1.1 (10)
N8—C31—C33—C32−177.0 (4)C55—C24—C54—C25−2.5 (8)
C30—C31—C33—C321.1 (6)O3—C24—C54—C25−178.1 (4)
N8—C31—C33—C343.6 (9)C26—C25—C54—C241.5 (8)
C30—C31—C33—C34−178.4 (5)C2—C3—C4—C52−3.5 (9)
N8—C31—C30—N9176.9 (4)O5—C3—C4—C52177.5 (5)
C33—C31—C30—N9−1.2 (5)C1—C52—C4—C32.7 (9)
N8—C31—C30—C290.1 (8)C46—C41—C42—C43−2.9 (8)
C33—C31—C30—C29−178.0 (4)N7—C41—C42—C43177.9 (5)
C32—N9—C30—C310.9 (5)C44—C43—C42—C410.2 (9)
C35—N9—C30—C31−173.2 (5)C13—C12—C17—C16−1.2 (10)
C32—N9—C30—C29177.3 (5)N5—C12—C17—C16176.3 (5)
C35—N9—C30—C293.2 (8)C15—C16—C17—C12−0.8 (11)
C31—C30—C29—O2178.4 (5)C39—C38—C37—C360.9 (9)
N9—C30—C29—O22.5 (9)C35—C36—C37—C38−0.6 (9)
C31—C30—C29—N7−2.6 (7)C42—C43—C44—F2−178.9 (5)
N9—C30—C29—N7−178.6 (4)C42—C43—C44—C452.1 (10)
C28—N7—C29—O2−174.8 (5)C46—C45—C44—C43−1.7 (11)
C41—N7—C29—O2−1.2 (7)C46—C45—C44—F2179.3 (5)
C28—N7—C29—C306.2 (6)C25—C26—C27—C55−2.2 (9)
C41—N7—C29—C30179.7 (4)O6—C26—C27—C55178.2 (5)
C54—C24—C55—C271.1 (8)C24—C55—C27—C261.3 (9)
O3—C24—C55—C27176.8 (5)O4—C55—C27—C2672.5 (5)
C54—C24—C55—O4−68.6 (5)C19—C18—C23—C22−2.0 (9)
O3—C24—C55—O4107.1 (4)N4—C18—C23—C22174.8 (5)
C5—O4—C55—C2434.7 (4)C17—C16—C15—C141.8 (13)
C1—O4—C55—C24−82.6 (4)C4—C3—C2—C532.3 (10)
C5—O4—C55—C27−88.7 (5)O5—C3—C2—C53−178.6 (6)
C1—O4—C55—C27154.0 (4)C20—C21—C22—C231.3 (11)
C25—C26—O6—C515.2 (8)F1—C21—C22—C23−177.7 (5)
C27—C26—O6—C51−175.2 (5)C18—C23—C22—C210.3 (10)
C5—N4—C18—C19−84.3 (7)C3—C2—C53—C1−0.2 (10)
C6—N4—C18—C1998.9 (6)C52—C1—C53—C2−0.6 (9)
C5—N4—C18—C2399.0 (7)O4—C1—C53—C2−178.2 (5)
C6—N4—C18—C23−77.8 (6)C16—C15—C14—C13−0.9 (14)
C30—N9—C32—C33−0.2 (6)C12—C13—C14—C15−1.2 (12)
C35—N9—C32—C33174.1 (4)C22—C21—C20—C19−1.2 (11)
C34—C33—C32—N9178.9 (5)F1—C21—C20—C19177.8 (5)
C31—C33—C32—N9−0.6 (6)C18—C19—C20—C21−0.6 (9)
C9—N5—C12—C13−73.7 (7)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C19—H19···O60.932.573.421 (8)152.
C38—H38···O2i0.932.613.405 (8)144.
C50—H50B···F1ii0.962.513.407 (7)155.
C15—H15···O1iii0.932.413.201 (9)143.

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT2753).

References

  • Bruker (2001). SMART and SAINT-Plus Bruker AXS Inc., Madison, Wisconsin, USA.
  • Ding, M. W., Xu, S. Z. & Zhao, J. F. (2004). J. Org. Chem.69, 8366–8371. [PubMed]
  • Niwas, S., Chand, P., Pathak, V. P. & Montgomery, J. A. (1994). J. Med. Chem.37, 2477–2480. [PubMed]
  • Sheldrick, G. M. (2003). SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Shih, H., Cottam, H. B. & Carson, D. A. (2002). Chem. Pharm. Bull.50, 364–367. [PubMed]
  • Spek, A. L. (2003). J. Appl. Cryst.36, 7–13.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography