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Acta Crystallogr Sect E Struct Rep Online. 2008 September 1; 64(Pt 9): o1689.
Published online 2008 August 6. doi:  10.1107/S1600536808023635
PMCID: PMC2960665

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)

Abstract

In the title compound, C26H32N8O6 2+·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.

Related literature

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

An external file that holds a picture, illustration, etc.
Object name is e-64-o1689-scheme1.jpg

Experimental

Crystal data

  • C26H32N8O6 2+·2BF4
  • M r = 726.22
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1689-efi1.jpg
  • a = 17.9399 (17) Å
  • b = 7.9673 (8) Å
  • c = 22.580 (2) Å
  • β = 93.089 (2)°
  • V = 3222.7 (5) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.14 mm−1
  • T = 298 (2) K
  • 0.36 × 0.30 × 0.26 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: none
  • 17389 measured reflections
  • 5673 independent reflections
  • 3356 reflections with I > 2σ(I)
  • R int = 0.079

Refinement

  • R[F 2 > 2σ(F 2)] = 0.066
  • wR(F 2) = 0.198
  • S = 0.96
  • 5673 reflections
  • 556 parameters
  • 45 restraints
  • H-atom parameters constrained
  • Δρmax = 0.39 e Å−3
  • Δρmin = −0.21 e Å−3

Data collection: SMART (Bruker, 2001 [triangle]); cell refinement: SAINT (Bruker, 2001 [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.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808023635/cv2429sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808023635/cv2429Isup2.hkl

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

Acknowledgments

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.

supplementary crystallographic information

Comment

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).

Experimental

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

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.

Figures

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.

Crystal data

C26H32N8O62+·2BF4F000 = 1496
Mr = 726.22Dx = 1.497 Mg m3
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 mm1
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

Bruker SMART CCD area-detector diffractometer3356 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

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 Å3
556 parametersΔρmin = −0.21 e Å3
45 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods

Special details

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

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

xyzUiso*/UeqOcc. (<1)
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)

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, °)

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, °)

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.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV2429).

References

  • Bruker (2001). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Wei, F.-Q. & Wu, A.-X. (2005). Acta Cryst. E61, o1453–o1455.
  • Wu, A., Fettinger, J. C. & Isaacs, L. (2002). Tetrahedron, 58, 9769–9777.

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