Download citation
Download citation
link to html
The title compound, C10H16N6O6, belongs to a family of compounds that contain the tetra­aza­bi­cyclo­[3.3.0]­octane ring system, and served as the precursor to the energetic material known as `bi­cyclo-HMX'. Both five-membered rings have envelope conformations, with methyl­ene C atoms displaced from the respective C2N2 planes towards the endo side of the bicyclic system by 0.466 (3) and 0.315 (4) Å for the di­nitro- and dipropionyl-substituted rings, respectively. The dihedral angle formed by the C2N2 planes is 118.1 (1)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802013570/ya6117sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802013570/ya6117Isup2.hkl
Contains datablock I

CCDC reference: 197459

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.004 Å
  • Disorder of main residue
  • R factor = 0.051
  • wR factor = 0.139
  • Data-to-parameter ratio = 11.0

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
REFLT_03 From the CIF: _diffrn_reflns_theta_max 67.00 From the CIF: _reflns_number_total 2410 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 2548 Completeness (_total/calc) 94.58% Alert C: < 95% complete
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check

Comment top

The title compound, (I), is one of a family of many compounds containing the tetraazabicyclo[3.3.0]octane ring system synthesized by Pagoria et al. (1996) and Koppes et al. (1987) as possible energetic materials or precursors to energetic materials. Compound (I) was the only precursor found that was successfully nitrolyzed to the target material known as `bicyclo-HMX', (II). This fully nitro-substituted product proved to be energetically equivalent to, but no better than HMX, a widely used component in explosive and propellant formulations. The crystal structure of (II) is reported in the article following this (Gilardi et al., 2002). Crystal structure analyses of several other derivatives of this ring system were reported by Koppes et al. (1987).

The bicyclic system in molecule (I) (Fig. 1) adopts a butterfly shape, with both five-membered rings having envelope conformations, best seen in Fig. 2. The methylene atoms C3 and C7 are displaced from the C1/C5/N2/N4 and C1/C5/N6/N8 planes by 0.466 (3) and 0.315 (4) Å, respectively; in both cases, they deviate towards the endo side of the bicyclic system. The dihedral angle measured between the two four-atom planes is 118.1 (1)°. The carbonyl groups of the two propionyl substituents are oriented in opposite directions relative to the C1—C5 bridgehead, with torsion angles C5—N6—C6—O6 and C1—N8—C8—O8 of 173.0 (5) and 1.5 (4)°, respectively. A similar reversal of direction has always been seen in the three earlier reports of diketo substitution on a ring of this same ring system. Such a fragment occurred twice in cis-2,4,6,8-tetraacetyl-1H,5H-2,4,6,8-tetraazabicyclo[3.3.0]octane (Koppes et al., 1987) and once in cis-6,8-diacetyl-2,4-dinitro-1H,5H-2,4,6,8-tetraazabicyclo[3.3.0]octane (Gilardi et al., 1992). The propionyl carbonyls and their attached atoms are roughly in the plane of the ring to which they are attached. In contrast, the two nitro substituents are bent far back from their adjacent ring, deviating towards the exo side of the ring system (Fig. 2). A measure of this bend is given by the dihedral angle between the plane through the NNO2 segment and the plane through the adjacent C—N—C segment of the ring. This dihedral angle is 41.0 (1)° for the nitro group on N2 and is 42.8 (2)° for the nitro group on N4. The four N atoms of the ring system are thus nearly planar in the one ring, and are highly pyramidalized in the other. (In the absence of any nitro twist, the out-of-plane dihedral angle would be 54.7° for a `tetrahedral' nitro-substituted N atom.) Nitramines are noted for the flexibility of their amine N atom; Gilardi & Karle (1991) reported that a range of 0–59° had been observed for the `bend angles' between the N—N bond and the adjacent C—N—C plane, a measure very similar to the dihedral angles reported here.

There is only one short intermolecular contact found in the crystal (see Fig. 3): the O8···H3Ai distance of 2.34 Å [symmetry code: (i) x, y − 1, z] is considerably less than the van der Waals distance of 2.72 Å (Rowland & Taylor, 1996).

Experimental top

A sample of the title compound was synthesized and crystallized by Clifford L. Coon of the Lawrence Livermore National Laboratory, using methods described in Pagoria et al. (1996).

Refinement top

The appearance of large difference peaks near the propionyl substituents on N6 prompted the use of a disordered model involving two conformations. The occupancies of the two forms were constrained to add to 1.0, and refined to a 79 (1):21 (1) ratio. All atoms in the disordered substituent were `split' into two images, even if there was no separate difference peak. The bond distances and angles of the two images, from N6 outwards along the propionyl chains, were strongly restrained to be equal, or nearly so (aiming toward a specified su of 0.001 Å for the differences). Thus the added refinement parameters were essentially just the torsion angles of the minor conformer and the occupation ratio. Atoms in the low-occupancy form have primed labels. H atoms were placed at ideal (Sheldrick, 1997) tetrahedral positions and allowed to ride on their bonded neighbors during the refinement, with periodic re-idealization. Methyl H atoms were allowed to torsion about the C—CH3 bond, except for the methyl group on the low-occupancy (21%) form of the propionyl on N6, which was fixed at a staggered location. The H-atom displacement parameters were specified to be isotropic, with a value equal to 1.5 times the Uequiv of the C atom for methyl groups, and equal to 1.2 times the Ueq value of the neighboring bonded atom for all other groups.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1997); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. A view of the title compound, (I), with 25% probability atomic displacement ellipsoids; only the major component of the disordered C6—C6A—C6B chain is shown. Both components of the disorder are shown in Fig. 2.
[Figure 2] Fig. 2. A view showing the cis-junction cleft between the two rings of the title compound. The disordered model of the C6 propionyl group is also shown. The conformer with dark bonds refined to an occupancy of 0.79 (1); the occupancies of both forms were constrained to add to 1. The propionyl group on N8 has been omitted for clarity.
[Figure 3] Fig. 3. : A view of the packing of the title compound down the b axis.
cis-(1H,5H)-2,4-dinitro-6,8-dipropionyl-2,4,6,8-tetraazabicyclo[3.3.0]octane top
Crystal data top
C10H16N6O6F(000) = 1328
Mr = 316.29Dx = 1.473 Mg m3
Monoclinic, C2/cCu Kα radiation, λ = 1.54178 Å
a = 23.8006 (4) ÅCell parameters from 5104 reflections
b = 6.1611 (1) Åθ = 3.9–67.0°
c = 20.2972 (4) ŵ = 1.06 mm1
β = 106.539 (1)°T = 295 K
V = 2853.20 (9) Å3Plate, colorless
Z = 80.28 × 0.11 × 0.03 mm
Data collection top
Bruker 6K CCD area-detector
diffractometer
2410 independent reflections
Radiation source: fine-focus sealed tube2178 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
ϕ and ω scansθmax = 67.0°, θmin = 4.5°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
h = 2725
Tmin = 0.744, Tmax = 0.969k = 76
7129 measured reflectionsl = 2323
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)] = 0.051H-atom parameters constrained
wR(F2) = 0.139 w = 1/[σ2(Fo2) + (0.0533P)2 + 4.0092P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max = 0.003
2410 reflectionsΔρmax = 0.22 e Å3
219 parametersΔρmin = 0.22 e Å3
9 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0046 (3)
Crystal data top
C10H16N6O6V = 2853.20 (9) Å3
Mr = 316.29Z = 8
Monoclinic, C2/cCu Kα radiation
a = 23.8006 (4) ŵ = 1.06 mm1
b = 6.1611 (1) ÅT = 295 K
c = 20.2972 (4) Å0.28 × 0.11 × 0.03 mm
β = 106.539 (1)°
Data collection top
Bruker 6K CCD area-detector
diffractometer
2410 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
2178 reflections with I > 2σ(I)
Tmin = 0.744, Tmax = 0.969Rint = 0.032
7129 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0519 restraints
wR(F2) = 0.139H-atom parameters constrained
S = 1.08Δρmax = 0.22 e Å3
2410 reflectionsΔρmin = 0.22 e Å3
219 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)
C10.31716 (9)0.1458 (4)0.40869 (11)0.0412 (5)
H1A0.31030.00800.38350.049*
N20.26493 (8)0.2162 (3)0.42863 (9)0.0420 (5)
N2A0.21351 (8)0.0913 (3)0.40236 (10)0.0462 (5)
O2A0.21930 (8)0.0965 (3)0.38920 (10)0.0617 (5)
O2B0.16732 (7)0.1809 (3)0.40008 (11)0.0668 (6)
C30.25804 (10)0.4497 (4)0.41659 (11)0.0440 (5)
H3A0.28000.53010.45670.053*
H3B0.21710.49110.40570.053*
N40.28113 (8)0.4906 (3)0.35825 (9)0.0425 (5)
N4A0.23977 (9)0.5029 (3)0.29337 (10)0.0476 (5)
O4A0.25838 (8)0.4912 (3)0.24352 (9)0.0608 (5)
O4B0.18898 (8)0.5391 (3)0.29132 (10)0.0631 (5)
C50.32940 (9)0.3333 (4)0.36366 (11)0.0431 (5)
H5A0.33040.28150.31840.052*
N60.38527 (8)0.4185 (3)0.40264 (10)0.0504 (5)
C60.4173 (2)0.5705 (10)0.3807 (3)0.0741 (19)0.794 (10)
O60.4613 (2)0.6432 (10)0.4217 (3)0.0939 (19)0.794 (10)
C6A0.3961 (2)0.6429 (14)0.3074 (3)0.099 (3)0.794 (10)
H6AA0.39170.51690.27770.119*0.794 (10)
H6AB0.35780.70940.29940.119*0.794 (10)
C6B0.4360 (2)0.7991 (15)0.2887 (3)0.155 (4)0.794 (10)
H6BA0.41970.84400.24190.233*0.794 (10)
H6BB0.47340.73140.29380.233*0.794 (10)
H6BC0.44100.92340.31830.233*0.794 (10)
C6'0.4143 (4)0.5961 (10)0.3898 (5)0.039 (5)*0.206 (10)
O6'0.4535 (6)0.674 (2)0.4366 (9)0.062 (5)*0.206 (10)
C6A'0.3965 (8)0.687 (2)0.3184 (8)0.059 (6)*0.206 (10)
H6AC0.35440.67270.29940.071*0.206 (10)
H6AD0.40590.84090.32050.071*0.206 (10)
C6B'0.4258 (11)0.579 (4)0.2722 (7)0.111 (8)*0.206 (10)
H6BD0.41380.64620.22780.166*0.206 (10)
H6BE0.41510.42820.26800.166*0.206 (10)
H6BF0.46750.59170.29090.166*0.206 (10)
C70.40433 (11)0.3334 (4)0.47248 (13)0.0527 (6)
H7A0.39600.43470.50510.063*
H7B0.44590.30000.48620.063*
N80.36900 (8)0.1371 (3)0.46654 (9)0.0451 (5)
C80.37859 (10)0.0332 (4)0.51113 (12)0.0470 (6)
O80.34387 (8)0.1824 (3)0.50160 (9)0.0633 (5)
C8A0.43305 (11)0.0222 (5)0.57118 (14)0.0599 (7)
H8AA0.46710.03310.55420.072*
H8AB0.43450.11810.59330.072*
C8B0.43629 (17)0.1968 (6)0.62354 (18)0.0917 (12)
H8BA0.46980.17240.66240.138*
H8BB0.43990.33560.60360.138*
H8BC0.40130.19420.63820.138*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0404 (11)0.0393 (12)0.0405 (11)0.0014 (9)0.0061 (9)0.0024 (9)
N20.0417 (10)0.0380 (10)0.0432 (10)0.0048 (7)0.0073 (8)0.0029 (8)
N2A0.0457 (11)0.0428 (12)0.0492 (11)0.0055 (8)0.0121 (8)0.0001 (8)
O2A0.0628 (11)0.0382 (10)0.0846 (13)0.0102 (8)0.0220 (9)0.0072 (8)
O2B0.0434 (10)0.0588 (12)0.0973 (15)0.0017 (8)0.0185 (9)0.0036 (10)
C30.0479 (12)0.0383 (12)0.0455 (12)0.0031 (9)0.0127 (10)0.0042 (9)
N40.0419 (10)0.0411 (11)0.0405 (10)0.0011 (7)0.0051 (8)0.0006 (7)
N4A0.0496 (12)0.0394 (11)0.0465 (11)0.0001 (8)0.0019 (9)0.0013 (8)
O4A0.0677 (12)0.0712 (12)0.0395 (9)0.0105 (9)0.0089 (8)0.0048 (8)
O4B0.0442 (10)0.0719 (13)0.0648 (11)0.0049 (8)0.0020 (8)0.0002 (9)
C50.0429 (12)0.0433 (13)0.0401 (11)0.0001 (9)0.0071 (9)0.0013 (9)
N60.0428 (11)0.0551 (12)0.0480 (11)0.0075 (9)0.0046 (8)0.0105 (9)
C60.048 (2)0.089 (3)0.078 (3)0.014 (2)0.0068 (19)0.032 (2)
O60.056 (2)0.117 (3)0.090 (3)0.042 (2)0.010 (2)0.046 (2)
C6A0.058 (3)0.143 (6)0.084 (4)0.026 (3)0.001 (2)0.060 (4)
C6B0.079 (3)0.247 (10)0.122 (5)0.050 (4)0.000 (3)0.109 (6)
C70.0473 (13)0.0525 (14)0.0489 (13)0.0100 (11)0.0017 (10)0.0082 (11)
N80.0425 (10)0.0402 (10)0.0455 (10)0.0033 (8)0.0011 (8)0.0045 (8)
C80.0473 (13)0.0412 (13)0.0482 (13)0.0004 (10)0.0067 (10)0.0019 (10)
O80.0657 (11)0.0456 (10)0.0655 (11)0.0125 (8)0.0021 (9)0.0086 (8)
C8A0.0524 (14)0.0565 (16)0.0607 (16)0.0035 (11)0.0004 (12)0.0116 (12)
C8B0.098 (2)0.076 (2)0.073 (2)0.0194 (18)0.0215 (18)0.0258 (17)
Geometric parameters (Å, º) top
C1—N81.442 (3)C6A—H6AB0.9700
C1—N21.478 (3)C6B—H6BA0.9600
C1—C51.551 (3)C6B—H6BB0.9600
C1—H1A0.9800C6B—H6BC0.9600
N2—N2A1.415 (2)C6'—O6'1.223 (4)
N2—C31.460 (3)C6'—C6A'1.498 (5)
N2A—O2A1.204 (3)C6A'—C6B'1.477 (6)
N2A—O2B1.219 (2)C6A'—H6AC0.9700
C3—N41.462 (3)C6A'—H6AD0.9700
C3—H3A0.9700C6B'—H6BD0.9600
C3—H3B0.9700C6B'—H6BE0.9600
N4—N4A1.404 (3)C6B'—H6BF0.9600
N4—C51.483 (3)C7—N81.458 (3)
N4A—O4A1.217 (3)C7—H7A0.9700
N4A—O4B1.218 (3)C7—H7B0.9700
C5—N61.439 (3)N8—C81.362 (3)
C5—H5A0.9800C8—O81.214 (3)
N6—C6'1.359 (3)C8—C8A1.507 (3)
N6—C61.359 (3)C8A—C8B1.499 (4)
N6—C71.457 (3)C8A—H8AA0.9700
C6—O61.223 (4)C8A—H8AB0.9700
C6—C6A1.498 (5)C8B—H8BA0.9600
C6A—C6B1.476 (6)C8B—H8BB0.9600
C6A—H6AA0.9700C8B—H8BC0.9600
N8—C1—N2112.29 (17)C6B—C6A—H6AB109.0
N8—C1—C5104.28 (17)C6—C6A—H6AB109.0
N2—C1—C5104.85 (17)H6AA—C6A—H6AB107.8
N8—C1—H1A111.7O6'—C6'—N6118.8 (3)
N2—C1—H1A111.7O6'—C6'—C6A'123.2 (3)
C5—C1—H1A111.7N6—C6'—C6A'117.9 (3)
N2A—N2—C3115.38 (17)C6B'—C6A'—C6'112.9 (4)
N2A—N2—C1116.22 (17)C6B'—C6A'—H6AC109.0
C3—N2—C1107.85 (17)C6'—C6A'—H6AC109.0
O2A—N2A—O2B125.8 (2)C6B'—C6A'—H6AD109.0
O2A—N2A—N2117.70 (19)C6'—C6A'—H6AD109.0
O2B—N2A—N2116.22 (19)H6AC—C6A'—H6AD107.8
N2—C3—N4104.79 (17)C6A'—C6B'—H6BD109.5
N2—C3—H3A110.8C6A'—C6B'—H6BE109.5
N4—C3—H3A110.8H6BD—C6B'—H6BE109.5
N2—C3—H3B110.8C6A'—C6B'—H6BF109.5
N4—C3—H3B110.8H6BD—C6B'—H6BF109.5
H3A—C3—H3B108.9H6BE—C6B'—H6BF109.5
N4A—N4—C3116.36 (18)N6—C7—N8101.86 (18)
N4A—N4—C5115.24 (17)N6—C7—H7A111.4
C3—N4—C5106.80 (17)N8—C7—H7A111.4
O4A—N4A—O4B125.1 (2)N6—C7—H7B111.4
O4A—N4A—N4116.92 (19)N8—C7—H7B111.4
O4B—N4A—N4117.8 (2)H7A—C7—H7B109.3
N6—C5—N4112.18 (18)C8—N8—C1120.82 (18)
N6—C5—C1104.29 (17)C8—N8—C7126.91 (19)
N4—C5—C1105.01 (17)C1—N8—C7112.10 (17)
N6—C5—H5A111.6O8—C8—N8120.0 (2)
N4—C5—H5A111.6O8—C8—C8A123.5 (2)
C1—C5—H5A111.6N8—C8—C8A116.5 (2)
C6'—N6—C611.2 (6)C8B—C8A—C8113.6 (2)
C6'—N6—C5129.0 (5)C8B—C8A—H8AA108.9
C6—N6—C5126.0 (2)C8—C8A—H8AA108.9
C6'—N6—C7116.2 (5)C8B—C8A—H8AB108.9
C6—N6—C7121.2 (3)C8—C8A—H8AB108.9
C5—N6—C7112.74 (18)H8AA—C8A—H8AB107.7
O6—C6—N6118.8 (3)C8A—C8B—H8BA109.5
O6—C6—C6A123.2 (3)C8A—C8B—H8BB109.5
N6—C6—C6A117.9 (3)H8BA—C8B—H8BB109.5
C6B—C6A—C6112.9 (4)C8A—C8B—H8BC109.5
C6B—C6A—H6AA109.0H8BA—C8B—H8BC109.5
C6—C6A—H6AA109.0H8BB—C8B—H8BC109.5
N8—C1—N2—N2A133.07 (18)C5—N6—C6—O6173.0 (5)
C5—C1—N2—N2A114.32 (19)C7—N6—C6—O63.4 (9)
N8—C1—N2—C395.6 (2)C6'—N6—C6—C6A116 (3)
C5—C1—N2—C317.0 (2)C5—N6—C6—C6A6.2 (9)
C3—N2—N2A—O2A154.9 (2)C7—N6—C6—C6A177.5 (5)
C1—N2—N2A—O2A27.2 (3)O6—C6—C6A—C6B4.0 (12)
C3—N2—N2A—O2B30.4 (3)N6—C6—C6A—C6B176.9 (9)
C1—N2—N2A—O2B158.2 (2)C6—N6—C6'—O6'119 (3)
N2A—N2—C3—N4100.8 (2)C5—N6—C6'—O6'161.9 (7)
C1—N2—C3—N431.0 (2)C7—N6—C6'—O6'0.6 (6)
N2—C3—N4—N4A97.4 (2)C6—N6—C6'—C6A'61 (3)
N2—C3—N4—C532.9 (2)C5—N6—C6'—C6A'18.2 (8)
C3—N4—N4A—O4A165.04 (19)C7—N6—C6'—C6A'179.4 (6)
C5—N4—N4A—O4A38.9 (3)O6'—C6'—C6A'—C6B'94.7 (17)
C3—N4—N4A—O4B19.9 (3)N6—C6'—C6A'—C6B'85.3 (17)
C5—N4—N4A—O4B146.0 (2)C6'—N6—C7—N8174.7 (5)
N4A—N4—C5—N6138.42 (19)C6—N6—C7—N8163.2 (5)
C3—N4—C5—N690.7 (2)C5—N6—C7—N820.0 (3)
N4A—N4—C5—C1108.92 (19)N2—C1—N8—C878.7 (3)
C3—N4—C5—C122.0 (2)C5—C1—N8—C8168.3 (2)
N8—C1—C5—N63.1 (2)N2—C1—N8—C796.8 (2)
N2—C1—C5—N6115.07 (18)C5—C1—N8—C716.2 (2)
N8—C1—C5—N4121.26 (18)N6—C7—N8—C8162.7 (2)
N2—C1—C5—N43.1 (2)N6—C7—N8—C122.1 (3)
N4—C5—N6—C6'60.7 (6)C1—N8—C8—O81.5 (4)
C1—C5—N6—C6'173.8 (5)C7—N8—C8—O8176.4 (2)
N4—C5—N6—C674.4 (5)C1—N8—C8—C8A177.9 (2)
C1—C5—N6—C6172.5 (5)C7—N8—C8—C8A3.1 (4)
N4—C5—N6—C7102.3 (2)O8—C8—C8A—C8B8.1 (4)
C1—C5—N6—C710.9 (3)N8—C8—C8A—C8B171.4 (3)
C6'—N6—C6—O663 (3)

Experimental details

Crystal data
Chemical formulaC10H16N6O6
Mr316.29
Crystal system, space groupMonoclinic, C2/c
Temperature (K)295
a, b, c (Å)23.8006 (4), 6.1611 (1), 20.2972 (4)
β (°) 106.539 (1)
V3)2853.20 (9)
Z8
Radiation typeCu Kα
µ (mm1)1.06
Crystal size (mm)0.28 × 0.11 × 0.03
Data collection
DiffractometerBruker 6K CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2001)
Tmin, Tmax0.744, 0.969
No. of measured, independent and
observed [I > 2σ(I)] reflections
7129, 2410, 2178
Rint0.032
(sin θ/λ)max1)0.597
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.051, 0.139, 1.08
No. of reflections2410
No. of parameters219
No. of restraints9
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.22, 0.22

Computer programs: SMART (Bruker, 2001), SMART, SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), SHELXTL (Sheldrick, 1997), SHELXTL.

 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds