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Acta Cryst. (2008). E64, o1689    [ doi:10.1107/S1600536808023635 ]

4,4'-[8b,8c-Bis(ethoxycarbonyl)-4,8-dioxo-2,3,5,6-tetrahydro-1H,4H-2,3a,4a,6,7a,8a-hexaazacyclopenta[def]fluorene-2,6-diyl]dipyridinium bis(tetrafluoridoborate)

S.-Q. Qin, T. Pang and Y.-T. Li

Abstract top

In the title compound, C26H32N8O62+·2BF4-, the cation is built up from four fused rings, viz. two nearly planar imidazole rings and two triazine rings exhibiting chair conformations. One ethoxy group is disordered between two positions in an approximate ratio 3:2. The F atoms of the two anions are each rotationally disordered between two orientations in the same 3:2 ratio. The crystal structure is stabilized by intermolecular N-H...O, C-H...F and N-H...F interactions.

Comment top

Glycoluril derivatives have many areas of applications, such as explosives, slow-release fertilizers, crosslinkers, iodogens, stabilisers of organic compounds against photodegradation, and reagent in combinatorial chemistry (Wu et al., 2002). In continuation of our previous studies in this area (Wei & Wu, 2005), we present the crystal structure of the title compound, (I) (Fig. 1).

All the geometrical parameters for (I) are normal - the distance between the two carbonyl oxygen atoms (O1 and O2) of the glycoluril moiety is 5.238 (5) Å. The distance between the centers of the two pyridyl rings is 7.386 (7) Å. Two pyridyl rings form a dihedral angle of 86.9 (3)°. The crystal packing is stabilized by intermolecular N—H···O, C—H···F and N—H···F interactions (Table 1).

Related literature top

For details of the applications of Glycoluril derivatives, see: Wei & Wu (2005); Wu et al. (2002).

Experimental top

A suspension of di(ethoxycarbonyl) glycoluril (1.43 g, 5 mmol) in 37% aq formaldehyde (3.5 ml) and MeOH (30 ml) was brought to reflux under magnetic stirring. Pyridin-4-ylmethanamine (15 mmol) in MeOH (20 ml) was slowly added dropwise (over 1 h) to the mixture. Then refluxing was continued. The reaction was monitored by TLC. The solvent was removed under reduced pressure and the products were separated by column chromatography (silica gel) with the yield 70%. X-ray quality crystals were grown from a Dichloromethane and Fluoboric acid solution at room temperature.

Refinement top

Positional disorder in the molecule was resolved with occupancies for the major and minor components refining to 0.62 (8) and 0.37 (2) for O4-C13-C14, 0.58 (5) and 0.41 (5) for F1-F2-F3-F4, 0.59 (2) and 0.40 (8) for F5-F6-F7-F8. All H atoms were positioned geometrically (C—H = 0.93–0.97 Å, N—H = 0.86 Å) and refined as riding, allowing for free rotation of methyl groups. The constraint Uiso (H) = 1.2Ueq (C, N) or 1.5Ueq (methyl C) was applied.

Computing details top

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

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) with 50% probability displacement ellipsoids (arbitrary spheres for H atoms). Only major components of the disordered groups of atoms are shown.
4,4'-[8b,8c-bis(ethoxycarbonyl)-4,8-dioxo-2,3,5,6-tetrahydro- 1H,4H-2,3a,4a,6,7a,8a-hexaazacyclopenta[def]fluorene- 2,6-diyl]dipyridinium bis(tetrafluoridoborate) top
Crystal data top
C26H32N8O62+·2BF4–F000 = 1496
Mr = 726.22Dx = 1.497 Mg m−3
Monoclinic, P21/nMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 3447 reflections
a = 17.9399 (17) Åθ = 2.7–21.9º
b = 7.9673 (8) ŵ = 0.14 mm−1
c = 22.580 (2) ÅT = 298 (2) K
β = 93.089 (2)ºBlock, yellow
V = 3222.7 (5) Å30.36 × 0.30 × 0.26 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer		3356 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.079
Monochromator: graphiteθmax = 25.0º
T = 298(2) Kθmin = 1.5º
phi and ω scansh = −20→21
Absorption correction: nonek = −9→9
17389 measured reflectionsl = −26→25
5673 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.066H-atom parameters constrained
wR(F2) = 0.198  w = 1/[σ2(Fo2) + (0.118P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.96(Δ/σ)max < 0.001
5673 reflectionsΔρmax = 0.39 e Å−3
556 parametersΔρmin = −0.21 e Å−3
45 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods
Crystal data top
C26H32N8O62+·2BF4–V = 3222.7 (5) Å3
Mr = 726.22Z = 4
Monoclinic, P21/nMo Kα
a = 17.9399 (17) ŵ = 0.14 mm−1
b = 7.9673 (8) ÅT = 298 (2) K
c = 22.580 (2) Å0.36 × 0.30 × 0.26 mm
β = 93.089 (2)º
Data collection top
Bruker SMART CCD area-detector
diffractometer		5673 independent reflections
Absorption correction: none3356 reflections with I > 2σ(I)
17389 measured reflectionsRint = 0.079
Refinement top
R[F2 > 2σ(F2)] = 0.06645 restraints
wR(F2) = 0.198H-atom parameters constrained
S = 0.96Δρmax = 0.39 e Å−3
5673 reflectionsΔρmin = −0.21 e Å−3
556 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*/UeqOcc. (<1)
C10.5001 (2)0.2921 (4)1.03044 (15)0.0681 (9)
H10.48250.32711.06640.082*
C20.57382 (18)0.3098 (4)1.01969 (14)0.0614 (8)
H20.60620.35961.04800.074*
C30.60061 (16)0.2541 (4)0.96692 (13)0.0525 (7)
C40.54954 (19)0.1868 (5)0.92583 (15)0.0774 (11)
H40.56530.14980.88950.093*
C50.4769 (2)0.1739 (6)0.93781 (16)0.0849 (12)
H50.44300.12880.90950.102*
C60.68192 (16)0.2666 (5)0.95544 (13)0.0603 (8)
H6A0.70190.36910.97320.072*
H6B0.70820.17280.97440.072*
C70.67801 (16)0.4271 (4)0.86354 (13)0.0609 (9)
H7A0.67400.41100.82090.073*
H7B0.62990.46570.87580.073*
C80.77071 (17)0.2133 (4)0.87916 (14)0.0607 (8)
H8A0.77140.18440.83750.073*
H8B0.78350.11320.90200.073*
C90.86504 (15)0.3565 (4)0.94858 (13)0.0533 (8)
C100.72970 (16)0.6712 (4)0.92212 (12)0.0544 (8)
C110.81079 (15)0.5083 (4)0.86883 (12)0.0522 (8)
C120.8258 (2)0.5248 (5)0.80193 (15)0.0698 (10)
O40.8874 (7)0.4592 (18)0.7910 (3)0.084 (3)0.372 (12)
C130.9117 (10)0.4813 (18)0.7335 (5)0.102 (5)0.372 (12)
H13A0.96530.49880.73520.122*0.372 (12)
H13B0.88790.57940.71540.122*0.372 (12)
C140.8922 (18)0.329 (2)0.6973 (6)0.172 (13)0.372 (12)
H14A0.89240.23190.72260.258*0.372 (12)
H14B0.92830.31360.66780.258*0.372 (12)
H14C0.84350.34240.67810.258*0.372 (12)
C13'0.8736 (5)0.3895 (17)0.7186 (3)0.119 (4)0.628 (12)
H13C0.84970.48590.69940.143*0.628 (12)
H13D0.85450.28880.69890.143*0.628 (12)
C14'0.9554 (5)0.3997 (17)0.7141 (4)0.135 (5)0.628 (12)
H14D0.97190.51210.72280.203*0.628 (12)
H14E0.96800.37010.67470.203*0.628 (12)
H14F0.97950.32350.74200.203*0.628 (12)
O4'0.8572 (4)0.3859 (10)0.7797 (2)0.0828 (19)0.628 (12)
C150.85621 (15)0.6300 (4)0.91047 (12)0.0524 (7)
C160.9183 (2)0.7291 (5)0.88022 (16)0.0695 (9)
C170.9536 (4)0.9832 (7)0.8373 (3)0.150 (2)
H17A0.97800.91520.80840.180*
H17B0.92771.07440.81640.180*
C181.0099 (4)1.0520 (9)0.8811 (4)0.213 (4)
H18A1.04780.96910.88990.320*
H18B0.98621.08110.91680.320*
H18C1.03241.15020.86510.320*
C190.91213 (16)0.5955 (5)1.01245 (13)0.0619 (9)
H19A0.92700.50801.04060.074*
H19B0.95500.66751.00770.074*
C200.82271 (18)0.8131 (4)0.99351 (13)0.0599 (8)
H20A0.86000.89850.98730.072*
H20B0.77980.86801.00930.072*
C210.79600 (17)0.5878 (5)1.06348 (12)0.0634 (9)
H21A0.78650.48901.03920.076*
H21B0.74960.64991.06510.076*
C220.82226 (16)0.5353 (4)1.12506 (13)0.0562 (8)
C230.8290 (2)0.6502 (5)1.17015 (14)0.0771 (10)
H230.82020.76331.16230.092*
C240.8490 (2)0.5984 (6)1.22743 (16)0.0879 (12)
H240.85350.67521.25840.105*
C250.8385 (2)0.3710 (5)1.13763 (16)0.0801 (10)
H250.83590.29171.10730.096*
C260.8587 (2)0.3221 (6)1.19426 (19)0.0905 (12)
H260.87020.21061.20280.109*
F10.4030 (7)0.5250 (14)0.7710 (4)0.224 (8)0.585 (14)
F20.4475 (4)0.2852 (6)0.8070 (3)0.107 (3)0.585 (14)
F30.3902 (5)0.4596 (10)0.8656 (3)0.159 (4)0.585 (14)
F40.5018 (5)0.5213 (11)0.8372 (6)0.181 (5)0.585 (14)
F1'0.4694 (10)0.5329 (16)0.8592 (5)0.179 (7)0.415 (14)
F2'0.4928 (11)0.334 (2)0.7966 (5)0.222 (10)0.415 (14)
F3'0.4150 (6)0.5340 (13)0.7668 (4)0.106 (4)0.415 (14)
F4'0.3802 (7)0.348 (3)0.8322 (9)0.250 (12)0.415 (14)
F50.2541 (3)0.9974 (8)0.8457 (3)0.112 (2)0.592 (9)
F60.2869 (4)0.8083 (8)0.9145 (3)0.130 (3)0.592 (9)
F70.3729 (2)0.9319 (5)0.86238 (15)0.0743 (16)0.592 (9)
F80.3161 (5)1.0776 (12)0.9308 (4)0.168 (5)0.592 (9)
F5'0.3113 (7)0.7954 (11)0.8864 (7)0.236 (10)0.408 (9)
F6'0.3243 (5)1.0241 (10)0.9440 (2)0.068 (2)0.408 (9)
F7'0.3375 (9)1.047 (3)0.8487 (3)0.399 (19)0.408 (9)
F8'0.2252 (4)0.9914 (10)0.8809 (5)0.122 (4)0.408 (9)
B10.4375 (3)0.4445 (7)0.8168 (2)0.114 (2)
B20.3046 (2)0.9579 (6)0.88888 (19)0.0864 (14)
N10.45360 (15)0.2244 (4)0.98903 (13)0.0729 (8)
H1A0.40720.21350.99600.088*
N20.69559 (13)0.2664 (3)0.89217 (10)0.0581 (7)
N30.82774 (12)0.3438 (3)0.89293 (10)0.0527 (6)
N40.73395 (12)0.5557 (3)0.87778 (10)0.0534 (6)
N50.89045 (13)0.5179 (3)0.95504 (10)0.0543 (7)
N60.79994 (13)0.7353 (3)0.93560 (10)0.0531 (6)
N70.85262 (13)0.6938 (3)1.03643 (10)0.0577 (7)
N80.86144 (19)0.4371 (5)1.23672 (13)0.0894 (10)
H80.87200.40451.27250.107*
O10.87551 (12)0.2428 (3)0.98316 (10)0.0709 (7)
O20.67268 (12)0.7166 (3)0.94438 (9)0.0708 (7)
O30.8013 (2)0.6342 (5)0.77298 (12)0.1221 (12)
O50.97363 (18)0.6629 (4)0.86828 (18)0.1354 (14)
O60.89909 (15)0.8793 (4)0.86841 (14)0.1023 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.073 (2)0.074 (2)0.059 (2)0.0090 (18)0.0190 (18)−0.0043 (17)
C20.0612 (19)0.071 (2)0.0521 (18)0.0020 (16)0.0021 (15)−0.0069 (16)
C30.0543 (17)0.061 (2)0.0429 (16)−0.0001 (14)0.0046 (13)0.0026 (14)
C40.066 (2)0.116 (3)0.0503 (19)−0.024 (2)0.0123 (16)−0.0186 (19)
C50.065 (2)0.130 (4)0.059 (2)−0.028 (2)−0.0003 (18)−0.006 (2)
C60.0514 (17)0.087 (2)0.0423 (16)−0.0085 (16)0.0040 (13)0.0037 (15)
C70.0502 (17)0.091 (3)0.0416 (16)0.0003 (17)0.0004 (13)0.0024 (16)
C80.0595 (19)0.068 (2)0.0561 (18)−0.0004 (16)0.0131 (15)−0.0044 (16)
C90.0419 (15)0.065 (2)0.0537 (18)0.0102 (15)0.0086 (13)0.0078 (16)
C100.0477 (18)0.073 (2)0.0424 (16)0.0111 (15)0.0033 (13)0.0159 (15)
C110.0475 (16)0.071 (2)0.0394 (15)0.0035 (14)0.0119 (12)0.0059 (14)
C120.070 (2)0.096 (3)0.0443 (19)−0.004 (2)0.0097 (16)0.010 (2)
O40.073 (7)0.141 (10)0.041 (4)0.005 (6)0.029 (4)−0.013 (4)
C130.109 (11)0.135 (13)0.065 (8)−0.019 (9)0.037 (8)−0.029 (7)
C140.33 (4)0.151 (16)0.047 (9)−0.120 (18)0.080 (13)−0.056 (9)
C13'0.155 (9)0.171 (12)0.037 (5)0.000 (8)0.043 (5)−0.027 (6)
C14'0.131 (8)0.181 (12)0.100 (7)0.013 (7)0.058 (6)0.019 (7)
O4'0.084 (4)0.116 (5)0.051 (3)0.008 (3)0.024 (3)−0.009 (3)
C150.0444 (15)0.068 (2)0.0463 (16)0.0054 (14)0.0121 (12)0.0079 (14)
C160.066 (2)0.077 (3)0.067 (2)0.0007 (19)0.0210 (17)0.0095 (19)
C170.131 (4)0.119 (4)0.207 (7)−0.017 (4)0.073 (5)0.059 (4)
C180.157 (6)0.196 (7)0.298 (10)−0.108 (6)0.110 (7)−0.109 (7)
C190.0492 (17)0.082 (2)0.0541 (18)−0.0028 (16)−0.0047 (14)0.0069 (17)
C200.0609 (18)0.068 (2)0.0511 (18)0.0042 (16)0.0077 (14)0.0024 (16)
C210.0565 (18)0.090 (3)0.0429 (16)−0.0060 (17)−0.0017 (13)0.0052 (16)
C220.0568 (18)0.066 (2)0.0456 (17)−0.0060 (15)0.0015 (13)0.0033 (16)
C230.102 (3)0.077 (3)0.051 (2)0.005 (2)−0.0010 (18)0.0020 (18)
C240.120 (3)0.090 (3)0.052 (2)0.002 (3)−0.005 (2)−0.002 (2)
C250.098 (3)0.077 (3)0.064 (2)−0.010 (2)−0.0044 (19)0.0000 (19)
C260.109 (3)0.076 (3)0.085 (3)−0.003 (2)−0.012 (2)0.019 (2)
F10.336 (19)0.150 (13)0.173 (12)0.027 (11)−0.087 (12)−0.006 (10)
F20.159 (6)0.071 (3)0.085 (4)−0.006 (3)−0.032 (4)−0.028 (2)
F30.193 (9)0.149 (6)0.136 (5)0.006 (5)0.004 (5)−0.070 (4)
F40.154 (6)0.135 (6)0.243 (12)0.009 (5)−0.098 (8)−0.046 (7)
F1'0.232 (18)0.161 (10)0.140 (8)−0.009 (11)−0.036 (9)−0.106 (7)
F2'0.34 (2)0.216 (16)0.103 (7)0.143 (15)−0.038 (12)−0.037 (9)
F3'0.142 (8)0.093 (9)0.080 (7)0.024 (6)−0.034 (6)−0.010 (6)
F4'0.162 (11)0.31 (2)0.28 (2)−0.112 (15)−0.040 (13)0.107 (18)
F50.102 (4)0.128 (4)0.102 (4)0.020 (3)−0.023 (3)0.024 (3)
F60.100 (4)0.181 (7)0.105 (4)−0.050 (4)−0.017 (3)0.065 (4)
F70.088 (3)0.096 (3)0.040 (2)0.007 (2)0.0069 (17)−0.0170 (18)
F80.079 (4)0.241 (10)0.185 (8)−0.010 (6)0.017 (5)−0.132 (8)
F5'0.176 (14)0.169 (13)0.35 (2)0.089 (11)−0.129 (14)−0.149 (14)
F6'0.078 (5)0.087 (4)0.040 (3)−0.001 (3)0.019 (3)−0.005 (3)
F7'0.38 (2)0.75 (4)0.066 (5)−0.40 (3)−0.036 (9)0.084 (13)
F8'0.115 (6)0.096 (5)0.152 (9)−0.011 (4)−0.041 (6)−0.016 (5)
B10.144 (6)0.121 (6)0.073 (4)0.010 (5)−0.030 (4)−0.020 (4)
B20.075 (3)0.104 (4)0.079 (3)−0.022 (3)−0.010 (3)0.001 (3)
N10.0493 (15)0.094 (2)0.076 (2)−0.0020 (14)0.0089 (14)0.0145 (17)
N20.0514 (14)0.0809 (19)0.0426 (14)−0.0030 (13)0.0077 (11)0.0029 (12)
N30.0486 (13)0.0657 (17)0.0446 (13)0.0046 (12)0.0099 (10)0.0045 (12)
N40.0462 (14)0.0745 (18)0.0398 (13)0.0085 (12)0.0047 (10)0.0058 (12)
N50.0453 (13)0.0681 (18)0.0495 (14)0.0053 (12)0.0027 (11)0.0071 (12)
N60.0493 (14)0.0675 (17)0.0432 (13)0.0062 (12)0.0081 (10)0.0060 (11)
N70.0521 (14)0.0757 (18)0.0452 (14)0.0003 (13)0.0016 (11)0.0054 (13)
N80.110 (3)0.104 (3)0.0519 (18)−0.011 (2)−0.0121 (16)0.0194 (19)
O10.0749 (15)0.0727 (16)0.0645 (14)0.0119 (12)−0.0024 (11)0.0169 (12)
O20.0494 (12)0.1031 (19)0.0607 (13)0.0187 (12)0.0108 (10)−0.0037 (12)
O30.174 (3)0.138 (3)0.0563 (16)0.045 (2)0.0260 (18)0.0357 (18)
O50.084 (2)0.127 (3)0.202 (4)0.016 (2)0.079 (2)0.053 (3)
O60.0888 (18)0.091 (2)0.131 (2)−0.0037 (16)0.0438 (17)0.0360 (18)
Geometric parameters (Å, °) top
C1—N11.334 (4)C15—C161.553 (4)
C1—C21.364 (5)C16—O51.169 (4)
C1—H10.9300C16—O61.269 (4)
C2—C31.382 (4)C17—C181.482 (9)
C2—H20.9300C17—O61.487 (5)
C3—C41.377 (4)C17—H17A0.9700
C3—C61.499 (4)C17—H17B0.9700
C4—C51.348 (5)C18—H18A0.9600
C4—H40.9300C18—H18B0.9600
C5—N11.314 (5)C18—H18C0.9600
C5—H50.9300C19—N71.452 (4)
C6—N21.462 (4)C19—N51.470 (4)
C6—H6A0.9700C19—H19A0.9700
C6—H6B0.9700C19—H19B0.9700
C7—N41.458 (4)C20—N71.441 (4)
C7—N21.461 (4)C20—N61.485 (4)
C7—H7A0.9700C20—H20A0.9700
C7—H7B0.9700C20—H20B0.9700
C8—N21.457 (4)C21—N71.478 (4)
C8—N31.480 (4)C21—C221.503 (4)
C8—H8A0.9700C21—H21A0.9700
C8—H8B0.9700C21—H21B0.9700
C9—O11.205 (3)C22—C251.368 (5)
C9—N51.369 (4)C22—C231.370 (5)
C9—N31.395 (4)C23—C241.386 (5)
C10—O21.219 (3)C23—H230.9300
C10—N41.365 (4)C24—N81.319 (5)
C10—N61.379 (4)C24—H240.9300
C11—N31.445 (4)C25—C261.367 (5)
C11—N41.454 (4)C25—H250.9300
C11—C151.551 (4)C26—N81.325 (5)
C11—C121.554 (4)C26—H260.9300
C12—O31.161 (4)F1—B11.341 (7)
C12—O41.258 (11)F2—B11.302 (7)
C12—O4'1.351 (8)F3—B11.431 (7)
O4—C131.402 (9)F4—B11.363 (7)
C13—C141.497 (10)F1'—B11.296 (8)
C13—H13A0.9700F2'—B11.418 (8)
C13—H13B0.9700F3'—B11.379 (7)
C14—H14A0.9600F4'—B11.345 (8)
C14—H14B0.9600F5—B21.332 (5)
C14—H14C0.9600F6—B21.370 (6)
C13'—O4'1.427 (7)F7—B21.409 (5)
C13'—C14'1.480 (9)F8—B21.352 (6)
C13'—H13C0.9700F5'—B21.301 (8)
C13'—H13D0.9700F6'—B21.380 (7)
C14'—H14D0.9600F7'—B21.319 (7)
C14'—H14E0.9600F8'—B21.451 (7)
C14'—H14F0.9600N1—H1A0.8600
C15—N61.451 (4)N8—H80.8600
C15—N51.456 (4)
N1—C1—C2119.5 (3)H20A—C20—H20B107.8
N1—C1—H1120.2N7—C21—C22110.7 (2)
C2—C1—H1120.2N7—C21—H21A109.5
C1—C2—C3120.4 (3)C22—C21—H21A109.5
C1—C2—H2119.8N7—C21—H21B109.5
C3—C2—H2119.8C22—C21—H21B109.5
C4—C3—C2117.2 (3)H21A—C21—H21B108.1
C4—C3—C6121.9 (3)C25—C22—C23118.4 (3)
C2—C3—C6121.0 (3)C25—C22—C21120.7 (3)
C5—C4—C3120.6 (3)C23—C22—C21120.8 (3)
C5—C4—H4119.7C22—C23—C24120.2 (4)
C3—C4—H4119.7C22—C23—H23119.9
N1—C5—C4120.7 (3)C24—C23—H23119.9
N1—C5—H5119.7N8—C24—C23118.1 (4)
C4—C5—H5119.7N8—C24—H24120.9
N2—C6—C3112.6 (2)C23—C24—H24120.9
N2—C6—H6A109.1C26—C25—C22120.6 (4)
C3—C6—H6A109.1C26—C25—H25119.7
N2—C6—H6B109.1C22—C25—H25119.7
C3—C6—H6B109.1N8—C26—C25118.5 (4)
H6A—C6—H6B107.8N8—C26—H26120.7
N4—C7—N2112.9 (2)C25—C26—H26120.7
N4—C7—H7A109.0F1'—B1—F2126.6 (8)
N2—C7—H7A109.0F1'—B1—F1118.5 (11)
N4—C7—H7B109.0F2—B1—F1113.4 (6)
N2—C7—H7B109.0F1'—B1—F4'115.7 (8)
H7A—C7—H7B107.8F2—B1—F4'66.5 (10)
N2—C8—N3112.9 (2)F1—B1—F4'98.4 (9)
N2—C8—H8A109.0F1'—B1—F434.4 (7)
N3—C8—H8A109.0F2—B1—F4111.9 (6)
N2—C8—H8B109.0F1—B1—F4113.1 (7)
N3—C8—H8B109.0F4'—B1—F4144.5 (8)
H8A—C8—H8B107.8F1'—B1—F3'115.0 (8)
O1—C9—N5126.7 (3)F2—B1—F3'113.7 (7)
O1—C9—N3125.4 (3)F1—B1—F3'10.4 (10)
N5—C9—N3107.8 (3)F4'—B1—F3'108.2 (6)
O2—C10—N4125.7 (3)F4—B1—F3'104.5 (8)
O2—C10—N6125.2 (3)F1'—B1—F2'106.6 (7)
N4—C10—N6109.0 (2)F2—B1—F2'40.3 (9)
N3—C11—N4111.4 (2)F1—B1—F2'110.4 (9)
N3—C11—C15104.2 (2)F4'—B1—F2'106.7 (8)
N4—C11—C15103.0 (2)F4—B1—F2'78.0 (8)
N3—C11—C12113.5 (3)F3'—B1—F2'103.6 (7)
N4—C11—C12109.2 (2)F1'—B1—F369.1 (7)
C15—C11—C12115.0 (3)F2—B1—F3107.8 (5)
O3—C12—O4120.7 (6)F1—B1—F3106.6 (7)
O3—C12—O4'124.0 (4)F4'—B1—F349.9 (9)
O4—C12—O4'36.7 (5)F4—B1—F3103.2 (5)
O3—C12—C11122.0 (4)F3'—B1—F3115.3 (7)
O4—C12—C11110.9 (5)F2'—B1—F3139.0 (9)
O4'—C12—C11112.9 (4)F5'—B2—F7'117.6 (8)
C12—O4—C13116.8 (11)F5'—B2—F5105.4 (7)
O4—C13—C14109.2 (9)F7'—B2—F571.4 (6)
O4—C13—H13A109.8F5'—B2—F8136.1 (8)
C14—C13—H13A109.8F7'—B2—F892.5 (8)
O4—C13—H13B109.8F5—B2—F8114.7 (6)
C14—C13—H13B109.8F5'—B2—F634.6 (8)
H13A—C13—H13B108.3F7'—B2—F6152.2 (9)
O4'—C13'—C14'108.9 (7)F5—B2—F6110.6 (5)
O4'—C13'—H13C109.9F8—B2—F6110.3 (6)
C14'—C13'—H13C109.9F5'—B2—F6'113.5 (7)
O4'—C13'—H13D109.9F7'—B2—F6'108.1 (6)
C14'—C13'—H13D109.9F5—B2—F6'134.5 (6)
H13C—C13'—H13D108.3F8—B2—F6'22.6 (6)
C13'—C14'—H14D109.5F6—B2—F6'90.3 (5)
C13'—C14'—H14E109.5F5'—B2—F775.6 (8)
H14D—C14'—H14E109.5F7'—B2—F749.8 (10)
C13'—C14'—H14F109.5F5—B2—F7107.3 (4)
H14D—C14'—H14F109.5F8—B2—F7107.3 (5)
H14E—C14'—H14F109.5F6—B2—F7106.2 (5)
C12—O4'—C13'117.0 (7)F6'—B2—F7104.6 (5)
N6—C15—N5111.1 (2)F5'—B2—F8'105.7 (6)
N6—C15—C11104.2 (2)F7'—B2—F8'106.7 (7)
N5—C15—C11102.9 (2)F5—B2—F8'40.6 (4)
N6—C15—C16114.1 (3)F8—B2—F8'94.0 (6)
N5—C15—C16109.3 (2)F6—B2—F8'88.0 (5)
C11—C15—C16114.6 (2)F6'—B2—F8'104.1 (6)
O5—C16—O6126.9 (3)F7—B2—F8'147.7 (6)
O5—C16—C15120.7 (4)C5—N1—C1121.6 (3)
O6—C16—C15112.3 (3)C5—N1—H1A119.2
C18—C17—O6109.4 (6)C1—N1—H1A119.2
C18—C17—H17A109.8C8—N2—C7110.2 (2)
O6—C17—H17A109.8C8—N2—C6113.8 (2)
C18—C17—H17B109.8C7—N2—C6112.8 (3)
O6—C17—H17B109.8C9—N3—C11110.8 (2)
H17A—C17—H17B108.2C9—N3—C8122.2 (2)
C17—C18—H18A109.5C11—N3—C8115.4 (2)
C17—C18—H18B109.5C10—N4—C11111.6 (2)
H18A—C18—H18B109.5C10—N4—C7124.8 (2)
C17—C18—H18C109.5C11—N4—C7115.7 (2)
H18A—C18—H18C109.5C9—N5—C15112.1 (2)
H18B—C18—H18C109.5C9—N5—C19124.0 (3)
N7—C19—N5113.0 (2)C15—N5—C19115.7 (3)
N7—C19—H19A109.0C10—N6—C15110.3 (2)
N5—C19—H19A109.0C10—N6—C20123.7 (2)
N7—C19—H19B109.0C15—N6—C20114.9 (2)
N5—C19—H19B109.0C20—N7—C19111.1 (2)
H19A—C19—H19B107.8C20—N7—C21114.6 (2)
N7—C20—N6113.1 (3)C19—N7—C21112.4 (3)
N7—C20—H20A109.0C24—N8—C26124.0 (3)
N6—C20—H20A109.0C24—N8—H8118.0
N7—C20—H20B109.0C26—N8—H8118.0
N6—C20—H20B109.0C16—O6—C17116.6 (3)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C5—H5···F7i0.932.243.124 (6)158
N1—H1A···O2ii0.862.092.825 (4)143
C1—H1···F1'ii0.932.162.882 (8)134
C2—H2···F3ii0.932.423.213 (8)143
C20—H20B···F8iii0.972.293.215 (8)160
C21—H21B···F8iii0.972.473.345 (10)149
C23—H23···F5iii0.932.333.191 (7)154
C24—H24···F3'iv0.932.573.264 (10)132
C26—H26···F1v0.932.483.337 (14)154
C7—H7B···F40.972.463.273 (9)142
Symmetry codes: (i) x, y−1, z; (ii) −x+1, −y+1, −z+2; (iii) −x+1, −y+2, −z+2; (iv) x+1/2, −y+3/2, z+1/2; (v) x+1/2, −y+1/2, z+1/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C5—H5···F7i0.932.243.124 (6)158
N1—H1A···O2ii0.862.092.825 (4)143
C1—H1···F1'ii0.932.162.882 (8)134
C2—H2···F3ii0.932.423.213 (8)143
C20—H20B···F8iii0.972.293.215 (8)160
C21—H21B···F8iii0.972.473.345 (10)149
C23—H23···F5iii0.932.333.191 (7)154
C24—H24···F3'iv0.932.573.264 (10)132
C26—H26···F1v0.932.483.337 (14)154
C7—H7B···F40.972.463.273 (9)142
Symmetry codes: (i) x, y−1, z; (ii) −x+1, −y+1, −z+2; (iii) −x+1, −y+2, −z+2; (iv) x+1/2, −y+3/2, z+1/2; (v) x+1/2, −y+1/2, z+1/2.
Acknowledgements top

The authors thank Dr Meng Xiang-Gao for the X-ray data collection, and Gansu Province Key Technology R&D Program (No. 0708GKCA041) for financial support.

references
References top

Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Wei, F.-Q. & Wu, A.-X. (2005). Acta Cryst. E61, o1453–o1455.

Wu, A., Fettinger, J. C. & Isaacs, L. (2002). Tetrahedron, 58, 9769–9777.