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

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ISSN: 2056-9890

1,2,7,8-Tetra­methyl-4,5-di­hydro-3a,5a-di­aza­pyrene ditriflate

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aSchool of Chemistry, University of Manchester, Manchester M13 9PL, England
*Correspondence e-mail: b.coe@manchester.ac.uk

(Received 23 August 2006; accepted 1 September 2006; online 8 September 2006)

The title structure, C18H20N22+·2CF3O3S, is the first to be reported for a diquaternized derivative of 3,4,7,8-tetra­methyl-1,10-phenanthroline.

Comment

Relevant background information on this work and comments on the title structure, (II)[link], together with that of the closely related salt 3,6-dimethyl-4,5-dihydro-3a,5a-diaza­pyrene ditrif­late, (I), can be found in the preceding paper (Coe, Fitzgerald & Raftery, 2006[Coe, B. J., Fitzgerald, E. C. & Raftery, J. (2006). Acta Cryst. E62, o4333-o4334.]). The mol­ecular structure of (II)[link] is shown in Fig. 1[link] and selected geometric parameters are given in Table 1[link].

[Scheme 1]
[Figure 1]
Figure 1
The asymmetric unit of (II)[link], showing 50% probability displacement ellipsoids.

Experimental

Salt (II)[link] was synthesized as reported previously (Coe, Curati & Fitzgerald, 2006[Coe, B. J., Curati, N. R. M. & Fitzgerald, E. C. (2006). Synthesis, pp. 146-150.]). Crystals suitable for single-crystal X-ray diffraction were obtained by slow diffusion of diethyl ether vapour into an acetone solution of (II)[link] at 295 K.

Crystal data
  • C18H20N22+·2CF3O3S

  • Mr = 562.50

  • Monoclinic, P 21 /c

  • a = 12.882 (1) Å

  • b = 8.152 (1) Å

  • c = 22.585 (1) Å

  • β = 104.284 (1)°

  • V = 2298.4 (2) Å3

  • Z = 4

  • Dx = 1.626 Mg m−3

  • Mo Kα radiation

  • μ = 0.32 mm−1

  • T = 100 (2) K

  • Block, white

  • 0.45 × 0.30 × 0.20 mm

Data collection
  • Bruker SMART APEX CCD diffractometer

  • φ and ω scans

  • Absorption correction: none

  • 19382 measured reflections

  • 5467 independent reflections

  • 4426 reflections with I > 2σ(I)

  • Rint = 0.058

  • θmax = 28.3°

Refinement
  • Refinement on F2

  • R[F2 > 2σ(F2)] = 0.047

  • wR(F2) = 0.131

  • S = 1.08

  • 5467 reflections

  • 329 parameters

  • H-atom parameters constrained

  • w = 1/[σ2(Fo2) + (0.0667P)2 + 1.2422P] where P = (Fo2 + 2Fc2)/3

  • (Δ/σ)max < 0.001

  • Δρmax = 0.81 e Å−3

  • Δρmin = −0.67 e Å−3

Table 1
Selected geometric parameters (Å, °)

C1—N1 1.364 (2)
C1—C9 1.404 (3)
C1—C2 1.433 (3)
C2—N2 1.369 (2)
C2—C6 1.399 (3)
C3—N2 1.330 (2)
C3—C4 1.393 (3)
C4—C5 1.385 (3)
C4—C15 1.505 (3)
C5—C6 1.430 (3)
C5—C16 1.501 (3)
C6—C7 1.435 (3)
C7—C8 1.355 (3)
C8—C9 1.434 (3)
C9—C10 1.427 (3)
C10—C11 1.388 (3)
C10—C17 1.501 (3)
C11—C12 1.395 (3)
C11—C18 1.503 (3)
C12—N1 1.329 (2)
C13—N1 1.483 (2)
C13—C14 1.504 (3)
C14—N2 1.479 (2)
N1—C1—C2 119.87 (17)
N2—C2—C1 119.65 (17)
N1—C13—C14 108.40 (15)
N2—C14—C13 108.35 (15)
C1—N1—C13 118.55 (15)
C2—N2—C14 117.71 (15)
N1—C13—C14—N2 −58.83 (19)

All H atoms were included in calculated positions, with C—H = 0.95 (CH), 0.99 (CH2) and 0.98 Å (CH3); Uiso(H) values were fixed at 1.2Ueq(C) or 1.5Ueq(methyl C).

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART. Version 5.625. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2003[Bruker (2003). SAINT. Version 6.45. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SIR2004 (Burla et al., 2005[Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381-388.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXL97. University of Göttingen, Germany.]); molecular graphics: SHELXTL (Bruker, 2000[Bruker (2000). SHELXTL. Version 6.10. Bruker AXS Inc., Madison, Wisconsin, USA.]); software used to prepare material for publication: SHELXTL.

Supporting information


Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.

1,2,7,8-Tetramethyl-4,5-dihydro-3a,5a-diazapyrene ditriflate top
Crystal data top
C18H20N22+·2CF3O3SF(000) = 1152
Mr = 562.50Dx = 1.626 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 7763 reflections
a = 12.8820 (7) Åθ = 2.8–28.2°
b = 8.1520 (4) ŵ = 0.32 mm1
c = 22.5850 (12) ÅT = 100 K
β = 104.284 (1)°Plate, white
V = 2298.4 (2) Å30.45 × 0.30 × 0.20 mm
Z = 4
Data collection top
Bruker SMART APEX CCD
diffractometer
4426 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.058
Graphite monochromatorθmax = 28.3°, θmin = 1.6°
φ and ω scansh = 1717
19382 measured reflectionsk = 1010
5467 independent reflectionsl = 2928
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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.0667P)2 + 1.2422P]
where P = (Fo2 + 2Fc2)/3
5467 reflections(Δ/σ)max < 0.001
329 parametersΔρmax = 0.81 e Å3
0 restraintsΔρmin = 0.67 e Å3
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.08483 (15)0.0957 (2)0.11781 (9)0.0156 (4)
C20.02962 (15)0.1074 (2)0.09903 (9)0.0156 (4)
C30.19641 (15)0.0541 (2)0.12015 (9)0.0176 (4)
H30.23600.00510.14580.021*
C40.25087 (15)0.1421 (2)0.06899 (9)0.0177 (4)
C50.19378 (16)0.2071 (2)0.03000 (9)0.0196 (4)
C60.07995 (15)0.1883 (2)0.04492 (9)0.0175 (4)
C70.01382 (16)0.2462 (3)0.00665 (9)0.0214 (4)
H70.04610.30250.03010.026*
C80.09358 (16)0.2223 (3)0.02173 (9)0.0211 (4)
H80.13420.25610.00600.025*
C90.14745 (15)0.1474 (2)0.07845 (9)0.0172 (4)
C100.26105 (15)0.1317 (2)0.09824 (9)0.0190 (4)
C110.30618 (15)0.0739 (2)0.15676 (9)0.0195 (4)
C120.23917 (15)0.0322 (2)0.19440 (9)0.0184 (4)
H120.27010.00450.23480.022*
C130.06579 (15)0.0115 (2)0.21866 (9)0.0168 (4)
H13A0.04870.11640.23620.020*
H13B0.10470.05940.25250.020*
C140.03566 (15)0.0715 (2)0.18461 (9)0.0165 (4)
H14A0.01870.17810.16820.020*
H14B0.08270.09210.21250.020*
C150.37036 (15)0.1594 (3)0.05822 (10)0.0217 (4)
H15A0.39050.27480.05040.032*
H15B0.39260.12160.09440.032*
H15C0.40590.09300.02280.032*
C160.25076 (18)0.2982 (3)0.02644 (10)0.0299 (5)
H16A0.32460.25840.03990.045*
H16B0.21370.27980.05890.045*
H16C0.25110.41570.01740.045*
C170.33141 (17)0.1812 (3)0.05728 (10)0.0259 (5)
H17A0.35470.29510.06590.039*
H17B0.29120.17160.01450.039*
H17C0.39430.10930.06470.039*
C180.42501 (16)0.0582 (3)0.18268 (10)0.0256 (5)
H18A0.45430.02100.15840.038*
H18B0.43910.02010.22510.038*
H18C0.45910.16520.18140.038*
C190.29745 (17)0.5445 (3)0.19959 (11)0.0245 (4)
C200.41878 (19)0.1440 (3)0.39136 (12)0.0326 (5)
F10.33941 (11)0.45210 (19)0.24792 (8)0.0426 (4)
F20.32142 (11)0.47396 (18)0.15109 (7)0.0379 (4)
F30.34766 (11)0.68971 (17)0.20785 (7)0.0354 (3)
F40.46066 (15)0.1354 (3)0.34373 (11)0.0848 (8)
F50.43790 (12)0.29605 (19)0.41287 (8)0.0491 (4)
F60.47371 (16)0.0461 (2)0.43370 (12)0.0923 (9)
N10.13323 (13)0.0425 (2)0.17525 (7)0.0153 (3)
N20.09044 (12)0.0369 (2)0.13402 (7)0.0152 (3)
O10.14522 (12)0.65279 (18)0.24348 (6)0.0224 (3)
O20.11371 (12)0.40314 (18)0.18258 (7)0.0243 (3)
O30.12341 (12)0.6681 (2)0.13390 (7)0.0257 (3)
O40.2466 (2)0.1162 (5)0.42530 (11)0.1106 (14)
O50.27358 (16)0.0663 (2)0.34630 (9)0.0495 (6)
O60.23670 (15)0.2165 (2)0.32313 (9)0.0448 (5)
S10.15330 (4)0.56891 (6)0.18837 (2)0.01698 (13)
S20.27643 (4)0.09789 (8)0.36958 (2)0.02868 (16)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0166 (9)0.0146 (9)0.0145 (9)0.0008 (7)0.0016 (7)0.0027 (7)
C20.0157 (9)0.0156 (9)0.0151 (9)0.0002 (7)0.0034 (7)0.0022 (7)
C30.0153 (9)0.0189 (9)0.0186 (9)0.0006 (7)0.0040 (7)0.0029 (7)
C40.0158 (9)0.0171 (9)0.0191 (9)0.0015 (7)0.0018 (7)0.0040 (7)
C50.0179 (9)0.0213 (10)0.0175 (9)0.0030 (7)0.0006 (7)0.0000 (8)
C60.0171 (9)0.0184 (9)0.0164 (9)0.0011 (7)0.0028 (7)0.0008 (7)
C70.0223 (10)0.0258 (11)0.0151 (9)0.0011 (8)0.0030 (8)0.0028 (8)
C80.0201 (10)0.0266 (11)0.0170 (9)0.0018 (8)0.0055 (7)0.0002 (8)
C90.0157 (9)0.0186 (9)0.0168 (9)0.0004 (7)0.0028 (7)0.0028 (7)
C100.0163 (9)0.0196 (10)0.0212 (10)0.0006 (7)0.0049 (7)0.0051 (8)
C110.0152 (9)0.0198 (10)0.0222 (10)0.0004 (7)0.0020 (7)0.0048 (8)
C120.0166 (9)0.0171 (9)0.0191 (9)0.0016 (7)0.0002 (7)0.0021 (7)
C130.0176 (9)0.0193 (9)0.0135 (9)0.0005 (7)0.0034 (7)0.0000 (7)
C140.0164 (9)0.0165 (9)0.0154 (9)0.0010 (7)0.0019 (7)0.0023 (7)
C150.0156 (9)0.0247 (10)0.0239 (10)0.0016 (8)0.0036 (8)0.0004 (8)
C160.0217 (11)0.0397 (14)0.0264 (11)0.0060 (9)0.0023 (9)0.0119 (10)
C170.0186 (10)0.0363 (13)0.0240 (11)0.0016 (9)0.0073 (8)0.0023 (9)
C180.0151 (10)0.0341 (12)0.0260 (11)0.0015 (8)0.0018 (8)0.0005 (9)
C190.0192 (10)0.0205 (10)0.0339 (12)0.0005 (8)0.0070 (9)0.0026 (9)
C200.0246 (11)0.0269 (12)0.0411 (14)0.0015 (9)0.0016 (10)0.0042 (10)
F10.0236 (7)0.0438 (9)0.0533 (10)0.0043 (6)0.0037 (6)0.0211 (7)
F20.0319 (7)0.0327 (8)0.0566 (10)0.0036 (6)0.0251 (7)0.0068 (7)
F30.0248 (7)0.0250 (7)0.0571 (9)0.0071 (5)0.0116 (6)0.0029 (6)
F40.0396 (10)0.127 (2)0.0984 (17)0.0115 (12)0.0374 (11)0.0415 (16)
F50.0384 (9)0.0333 (8)0.0651 (11)0.0111 (7)0.0075 (8)0.0052 (8)
F60.0620 (12)0.0471 (11)0.1228 (19)0.0214 (9)0.0630 (13)0.0411 (12)
N10.0152 (8)0.0154 (8)0.0144 (8)0.0002 (6)0.0020 (6)0.0013 (6)
N20.0150 (8)0.0155 (8)0.0145 (8)0.0006 (6)0.0024 (6)0.0006 (6)
O10.0299 (8)0.0199 (7)0.0184 (7)0.0013 (6)0.0078 (6)0.0024 (6)
O20.0233 (8)0.0209 (8)0.0288 (8)0.0034 (6)0.0065 (6)0.0061 (6)
O30.0264 (8)0.0315 (8)0.0190 (7)0.0069 (6)0.0051 (6)0.0044 (6)
O40.0672 (17)0.236 (4)0.0405 (13)0.080 (2)0.0354 (12)0.0597 (19)
O50.0530 (12)0.0271 (9)0.0497 (12)0.0114 (8)0.0231 (9)0.0104 (8)
O60.0371 (10)0.0260 (9)0.0555 (12)0.0093 (7)0.0188 (9)0.0055 (8)
S10.0166 (2)0.0177 (2)0.0162 (2)0.00113 (17)0.00335 (17)0.00091 (18)
S20.0228 (3)0.0432 (4)0.0186 (3)0.0093 (2)0.0025 (2)0.0046 (2)
Geometric parameters (Å, º) top
C1—N11.364 (2)C14—H14A0.9900
C1—C91.404 (3)C14—H14B0.9900
C1—C21.433 (3)C15—H15A0.9800
C2—N21.369 (2)C15—H15B0.9800
C2—C61.399 (3)C15—H15C0.9800
C3—N21.330 (2)C16—H16A0.9800
C3—C41.393 (3)C16—H16B0.9800
C3—H30.9500C16—H16C0.9800
C4—C51.385 (3)C17—H17A0.9800
C4—C151.505 (3)C17—H17B0.9800
C5—C61.430 (3)C17—H17C0.9800
C5—C161.501 (3)C18—H18A0.9800
C6—C71.435 (3)C18—H18B0.9800
C7—C81.355 (3)C18—H18C0.9800
C7—H70.9500C19—F11.326 (3)
C8—C91.434 (3)C19—F21.339 (3)
C8—H80.9500C19—F31.340 (2)
C9—C101.427 (3)C19—S11.822 (2)
C10—C111.388 (3)C20—F61.311 (3)
C10—C171.501 (3)C20—F41.319 (3)
C11—C121.395 (3)C20—F51.332 (3)
C11—C181.503 (3)C20—S21.817 (2)
C12—N11.329 (2)O1—S11.4461 (15)
C12—H120.9500O2—S11.4389 (15)
C13—N11.483 (2)O3—S11.4430 (15)
C13—C141.504 (3)O4—S21.411 (2)
C13—H13A0.9900O5—S21.435 (2)
C13—H13B0.9900O6—S21.4257 (19)
C14—N21.479 (2)
N1—C1—C9119.88 (17)C4—C15—H15C109.5
N1—C1—C2119.87 (17)H15A—C15—H15C109.5
C9—C1—C2120.15 (17)H15B—C15—H15C109.5
N2—C2—C6119.61 (17)C5—C16—H16A109.5
N2—C2—C1119.65 (17)C5—C16—H16B109.5
C6—C2—C1120.73 (17)H16A—C16—H16B109.5
N2—C3—C4121.80 (18)C5—C16—H16C109.5
N2—C3—H3119.1H16A—C16—H16C109.5
C4—C3—H3119.1H16B—C16—H16C109.5
C5—C4—C3119.13 (17)C10—C17—H17A109.5
C5—C4—C15122.96 (18)C10—C17—H17B109.5
C3—C4—C15117.90 (18)H17A—C17—H17B109.5
C4—C5—C6118.93 (17)C10—C17—H17C109.5
C4—C5—C16120.29 (18)H17A—C17—H17C109.5
C6—C5—C16120.77 (18)H17B—C17—H17C109.5
C2—C6—C5118.95 (18)C11—C18—H18A109.5
C2—C6—C7117.71 (17)C11—C18—H18B109.5
C5—C6—C7123.34 (18)H18A—C18—H18B109.5
C8—C7—C6121.52 (18)C11—C18—H18C109.5
C8—C7—H7119.2H18A—C18—H18C109.5
C6—C7—H7119.2H18B—C18—H18C109.5
C7—C8—C9121.64 (18)F1—C19—F2107.46 (18)
C7—C8—H8119.2F1—C19—F3107.60 (18)
C9—C8—H8119.2F2—C19—F3107.00 (17)
C1—C9—C10118.68 (17)F1—C19—S1111.77 (15)
C1—C9—C8117.79 (17)F2—C19—S1111.47 (15)
C10—C9—C8123.43 (18)F3—C19—S1111.30 (14)
C11—C10—C9119.01 (18)F6—C20—F4107.9 (3)
C11—C10—C17120.21 (18)F6—C20—F5106.4 (2)
C9—C10—C17120.76 (18)F4—C20—F5105.7 (2)
C10—C11—C12119.09 (18)F6—C20—S2113.50 (18)
C10—C11—C18123.14 (19)F4—C20—S2110.91 (18)
C12—C11—C18117.75 (18)F5—C20—S2112.01 (17)
N1—C12—C11121.79 (18)C12—N1—C1121.42 (17)
N1—C12—H12119.1C12—N1—C13119.76 (16)
C11—C12—H12119.1C1—N1—C13118.55 (15)
N1—C13—C14108.40 (15)C3—N2—C2121.33 (16)
N1—C13—H13A110.0C3—N2—C14120.74 (16)
C14—C13—H13A110.0C2—N2—C14117.71 (15)
N1—C13—H13B110.0O2—S1—O3115.78 (9)
C14—C13—H13B110.0O2—S1—O1115.03 (9)
H13A—C13—H13B108.4O3—S1—O1114.08 (9)
N2—C14—C13108.35 (15)O2—S1—C19103.66 (9)
N2—C14—H14A110.0O3—S1—C19103.20 (10)
C13—C14—H14A110.0O1—S1—C19102.66 (10)
N2—C14—H14B110.0O4—S2—O6117.2 (2)
C13—C14—H14B110.0O4—S2—O5115.9 (2)
H14A—C14—H14B108.4O6—S2—O5113.02 (11)
C4—C15—H15A109.5O4—S2—C20102.44 (13)
C4—C15—H15B109.5O6—S2—C20102.36 (12)
H15A—C15—H15B109.5O5—S2—C20103.00 (12)
N1—C1—C2—N212.2 (3)C18—C11—C12—N1179.98 (18)
C9—C1—C2—N2171.28 (17)N1—C13—C14—N258.83 (19)
N1—C1—C2—C6168.58 (17)C11—C12—N1—C10.5 (3)
C9—C1—C2—C67.9 (3)C11—C12—N1—C13174.41 (17)
N2—C3—C4—C52.9 (3)C9—C1—N1—C122.6 (3)
N2—C3—C4—C15178.04 (18)C2—C1—N1—C12179.12 (17)
C3—C4—C5—C62.7 (3)C9—C1—N1—C13171.34 (17)
C15—C4—C5—C6178.30 (18)C2—C1—N1—C135.2 (3)
C3—C4—C5—C16178.20 (19)C14—C13—N1—C12145.00 (17)
C15—C4—C5—C160.8 (3)C14—C13—N1—C140.9 (2)
N2—C2—C6—C55.1 (3)C4—C3—N2—C21.1 (3)
C1—C2—C6—C5175.67 (17)C4—C3—N2—C14173.38 (17)
N2—C2—C6—C7173.98 (18)C6—C2—N2—C35.1 (3)
C1—C2—C6—C75.2 (3)C1—C2—N2—C3175.66 (17)
C4—C5—C6—C21.2 (3)C6—C2—N2—C14169.46 (17)
C16—C5—C6—C2177.84 (19)C1—C2—N2—C149.7 (2)
C4—C5—C6—C7177.84 (19)C13—C14—N2—C3139.88 (18)
C16—C5—C6—C73.1 (3)C13—C14—N2—C245.5 (2)
C2—C6—C7—C80.7 (3)F1—C19—S1—O257.66 (18)
C5—C6—C7—C8178.4 (2)F2—C19—S1—O262.62 (17)
C6—C7—C8—C94.0 (3)F3—C19—S1—O2178.00 (15)
N1—C1—C9—C104.4 (3)F1—C19—S1—O3178.78 (16)
C2—C1—C9—C10179.06 (17)F2—C19—S1—O358.49 (17)
N1—C1—C9—C8171.96 (17)F3—C19—S1—O360.88 (18)
C2—C1—C9—C84.5 (3)F1—C19—S1—O162.40 (17)
C7—C8—C9—C11.3 (3)F2—C19—S1—O1177.32 (14)
C7—C8—C9—C10174.9 (2)F3—C19—S1—O157.94 (18)
C1—C9—C10—C113.3 (3)F6—C20—S2—O459.4 (3)
C8—C9—C10—C11172.95 (19)F4—C20—S2—O4178.9 (3)
C1—C9—C10—C17178.44 (18)F5—C20—S2—O461.1 (3)
C8—C9—C10—C175.4 (3)F6—C20—S2—O6178.7 (2)
C9—C10—C11—C120.3 (3)F4—C20—S2—O657.1 (2)
C17—C10—C11—C12178.57 (19)F5—C20—S2—O660.7 (2)
C9—C10—C11—C18177.92 (19)F6—C20—S2—O561.2 (2)
C17—C10—C11—C180.4 (3)F4—C20—S2—O560.4 (2)
C10—C11—C12—N11.7 (3)F5—C20—S2—O5178.22 (18)
 

Acknowledgements

The authors thank the EPSRC for funding (grant GR/R81459 and a PhD studentship).

References

First citationBruker (2000). SHELXTL. Version 6.10. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationBruker (2001). SMART. Version 5.625. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationBruker (2003). SAINT. Version 6.45. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationBurla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381–388.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationCoe, B. J., Curati, N. R. M. & Fitzgerald, E. C. (2006). Synthesis, pp. 146–150.  Web of Science CrossRef Google Scholar
First citationCoe, B. J., Fitzgerald, E. C. & Raftery, J. (2006). Acta Cryst. E62, o4333–o4334.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (1997). SHELXL97. University of Göttingen, Germany.  Google Scholar

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