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Subject to packing with different anions, the title cation undergoes various conformational changes with significantly different N—C—C—C torsion angles, as well as different angles between the NCN2 guanidine planes. The 2,2-(propane-1,3-di­yl)bis­(1,1,3,3-tetra­methyl­guanidinium) salts reported here, viz. the dibromide, C13H32N62+·2Br, the tetra­phenyl­borate chloride, C13H32N62+·C24H20B·Cl, the tetra­chloro­mercurate, (C13H32N6)[HgCl4], and the bis­(trifluoro­methanesulfonate), C13H32N62+·2CF3SO3, are dominated by strong inter­molecular N—H...X hydrogen bonds, which form different packing patterns.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270106014429/fg3012sup1.cif
Contains datablocks I, II, III, IV, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270106014429/fg3012Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270106014429/fg3012IIsup3.hkl
Contains datablock h988

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270106014429/fg3012IIIsup4.hkl
Contains datablock s990

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270106014429/fg3012IVsup5.hkl
Contains datablock h957

CCDC references: 612433; 612434; 612435; 612436

Comment top

The series of four structures presented here consists of protonated bis-guanidine cations, [btmgpH2]2+, crystallized with different anions, viz. (I) with Br (Fig. 1), (II) with [BPh4] and Cl (Fig. 2), (III) with [HgCl4]2− (Fig. 3) and (IV) with [CF3SO3] (triflat) (Fig. 4). Already known from ealier work is an initial member of this series, namely the structure (V) with Cl (Pohl et al., 2000). Although isomolecular with (V), the structure of (I) is not isotypic but exhibits two independent molecules, (IA) and (IB), with different conformations per asymmetric unit. As expected, the bond length parameters for the [btmgpH2]2+ moieties of all structures are very similar [C—C = 1.504 (2)–1.536 (7) Å, NC(propyl) = 1.455 (6)–1.477 (6) Å, NC = 1.326 (7)–1.341 (6) Å and C–N(guanidyl) = 1.331 (2)–1.343 (3) Å]. The N—C—C and C—C—C angles range from 109.1 (2) to 111.9 (2)° and 109.1 (3) to 114.1 (2)°, respectively.

Significant geometric differences, however, associated with the different packing patterns, are noted for the N—C—C—C torsion angles, which are given in Table 1. Fig. 5 depicts these different conformations. Likewise, the angles between the two NCN2 guanidine planes of each ligand cation differ markedly, being 15.5 (3)° for (Ia), 24.7 (3)° for (Ib), 67.00 (7)° for (II), 74.1 (1)° for (III), 67.23 (7)° for (IV) and 82.60 (6)° for (V). The relative orientations of the pairs of CNMe2 planes, on the other hand, are again very similar for all structures and their corresponding dihedral angles lie in the narrow range 52.1 (1)–56.1 (1)°. Only the conformation of cation (III) shows approximatively Cs symmetry, with a non-crystallographic mirror plane running through C2 and the attached H atoms; the other cations have C1 point-group symmetry.

Cmpounds (II) and (III) each pack with two intermolecular cation–anion N—H···Cl hydrogen bonds of similar geometries (Table 2). In (II) (Fig. 6), centrosymmetric dimeric units each with two cations and anions are formed, which are stacked along [010]. In (III) (Fig. 7), the two Cl acceptors, Cl1 and Cl4, of each anion bridge to the two NH sites of a cation; additionally, a C—H···Cl interaction from Cl3 connects this cation–anion pair to another cation site. Compound (I) exhibits N—H···Br interactions with short (2.4–2.5 Å) H.·Br distances and weaker C—H···Br interactions with an H···Br distance of about 2.8 Å, which link the (Ia) and (Ib) cations into a common network. In (IV), two strong N—H···O bridges link the cation to two triflat anions, thus forming 1:2 cation–anion units, which are then connected by C–H.·O interactions in a zigzag manner along [001]. The BPh4 and HgCl4 anions of (II) and (III) exhibit no unusual features and need no further discussion. The SO3 group of the triflat anion 1 in (IV) is disordered around the C—-S axis over two positions with occupation factors 0.919 (4) and 0.081 (4).

Experimental top

For the preparation of (I) and (III), to a solution of MnBr2 (215 mg) or HgCl2 (271.5 mg) (1 mmol), respectively, in acetonitrile (aqueous, 15 ml) was added btmgp (270 mg, 1 mmol); the mixture was stirred for 15 min at room temperature and then refluxed for a further 15 min. Colourless crystals were obtained using the vapor pressure equalization method with this solution in the presence of isopropylether. For the preparation of (II), a solution of PtCl2 (266 mg, 1 mmol) in acetonitrile (15 ml) was combined with btmgpg (270 mg, 1 mmol) and the mixture was stirred for 15 min at room temperature. NaBPh4 (342 mg, 1 mmol) was then added and the mixture was stirred for a further 15 min. Colourless crystals were obtained using the vapor pressure equalization method with this solution in the presence of isopropylether. For the preparation of (IV), to a solution of btmgp (270 mg, 1 mmol) in MeCN (10 ml) was added trifluoracetic acid (251 mg, 2.2 mmol) dropwise and the reaction mixture was then refluxed for 1 h. Crystals were grown by slow diffusion of diethylether into the colorless reaction solution.

Refinement top

H atoms were placed at idealized positions and treated as riding on their C atoms, with Uiso(H) values of 1.2Ueq(C) or 1.5Ueq(CH3). All CH3 groups were allowed to rotate but not to tip. The S—O bond geometry of the disordered triflat group in (IV) was been restrained with SADI (SHELXTL) [specify what this means in practice, for the benefit of readers who do not use this software]. Atoms O112–O132 of the minor part [occupation factor 0.081 (4)] were refined isotropically.

Computing details top

For all compounds, data collection: SMART (Bruker, 2002); cell refinement: SMART. Data reduction: SAINT (Bruker, 2002) for (I), (III), (IV); SAINT (Bruker, 2002 for (II). Program(s) used to solve structure: SHELXTL (Bruker, 2002) for (I), (III), (IV); SHELXTL (Bruker, 2002 for (II). For all compounds, program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), with broken lines showing the hydrogen bridging bonds. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. The molecular structure of (II), with broken lines showing the hydrogen bridging bonds; H atoms of the BPh4 group have been omitted. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 3] Fig. 3. The molecular structure of (III), with broken lines showing the hydrogen bridging bonds. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 4] Fig. 4. The molecular structure of (IV), with broken lines showing the hydrogen bridging bonds; the minor component of the disordered triflat anion omitted. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 5] Fig. 5. Cations of (Ia)–(V) (labelled #1 A–#5), showing different conformations with common N1, C3 and C4 positions.
[Figure 6] Fig. 6. Part of the crystal packing of (II), with the hydrogen-bonding pattern indicated as dashed lines. BPh4 cations and H atoms not involved in the interactions shown have been omitted. The asterisk (*) denotes symmetry-equivalent positions (−x + 1, −y, −z + 1).
[Figure 7] Fig. 7. Part of crystal packing of (III), with the hydrogen-bonding pattern indicated as dashed lines. H atoms not involved in the interactions shown ave been omitted. The asterisk (*) denotes symmetry equivalent positions (x − 1, y, z).
(I) 2,2-(propane-1,3-diyl)bis(1,1,3,3-tetramethylguanidinium) dibromide top
Crystal data top
C13H32N62+·2BrZ = 4
Mr = 432.27F(000) = 888
Triclinic, P1Dx = 1.478 Mg m3
a = 12.4256 (14) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.5254 (15) ÅCell parameters from 3469 reflections
c = 12.6935 (15) Åθ = 2.3–24.0°
α = 79.465 (3)°µ = 4.18 mm1
β = 89.731 (3)°T = 120 K
γ = 89.361 (2)°Prism, colourless
V = 1942.1 (4) Å30.42 × 0.22 × 0.20 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
9242 independent reflections
Radiation source: sealed tube5769 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.065
ϕ and ω scansθmax = 27.9°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
h = 1516
Tmin = 0.243, Tmax = 0.435k = 1616
19556 measured reflectionsl = 1616
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)] = 0.058Hydrogen site location: difference Fourier map
wR(F2) = 0.139H-atom parameters constrained
S = 0.99 w = 1/[σ2(Fo2) + (0.044P)2]
where P = (Fo2 + 2Fc2)/3
9242 reflections(Δ/σ)max = 0.001
387 parametersΔρmax = 0.95 e Å3
0 restraintsΔρmin = 0.89 e Å3
Crystal data top
C13H32N62+·2Brγ = 89.361 (2)°
Mr = 432.27V = 1942.1 (4) Å3
Triclinic, P1Z = 4
a = 12.4256 (14) ÅMo Kα radiation
b = 12.5254 (15) ŵ = 4.18 mm1
c = 12.6935 (15) ÅT = 120 K
α = 79.465 (3)°0.42 × 0.22 × 0.20 mm
β = 89.731 (3)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
9242 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
5769 reflections with I > 2σ(I)
Tmin = 0.243, Tmax = 0.435Rint = 0.065
19556 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0580 restraints
wR(F2) = 0.139H-atom parameters constrained
S = 0.99Δρmax = 0.95 e Å3
9242 reflectionsΔρmin = 0.89 e Å3
387 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*/Ueq
Br10.21776 (5)0.65444 (5)0.95708 (5)0.03482 (17)
Br20.72816 (5)0.80904 (4)0.70951 (4)0.03285 (16)
Br30.22558 (5)0.15980 (5)0.78783 (4)0.03379 (16)
Br40.71426 (4)0.33765 (4)0.57236 (5)0.03097 (15)
N110.3247 (3)0.4184 (3)0.9363 (3)0.0233 (10)
H110.29710.48420.93080.028*
N120.4455 (4)0.4830 (4)0.8021 (4)0.0292 (11)
N130.4859 (3)0.3269 (4)0.9222 (4)0.0271 (10)
N140.1088 (3)0.1451 (3)1.0304 (3)0.0229 (10)
H140.13140.13770.96630.027*
N150.0292 (3)0.0492 (3)1.1836 (3)0.0220 (9)
N160.1701 (3)0.0278 (3)1.1025 (3)0.0245 (10)
N210.8200 (3)0.5801 (3)0.5462 (4)0.0267 (10)
H210.79710.51320.56590.032*
N220.9398 (4)0.5614 (4)0.6873 (4)0.0307 (11)
N230.9751 (4)0.6806 (4)0.5286 (4)0.0307 (11)
N240.6106 (3)0.8538 (3)0.4642 (3)0.0237 (10)
H240.63590.85390.52880.028*
N250.6791 (4)1.0246 (3)0.4010 (3)0.0247 (10)
N260.5286 (3)0.9661 (3)0.3201 (3)0.0232 (10)
C110.0799 (4)0.2554 (4)1.0469 (4)0.0255 (12)
H10A0.09250.26091.12260.031*
H10B0.00240.26921.03150.031*
C120.1459 (4)0.3401 (4)0.9746 (4)0.0262 (12)
H10C0.13380.33360.89900.031*
H10D0.12120.41330.98360.031*
C130.2647 (4)0.3282 (4)0.9986 (4)0.0272 (12)
H10E0.27650.32641.07600.033*
H10F0.29160.25880.98130.033*
C140.4183 (4)0.4077 (4)0.8872 (4)0.0245 (12)
C150.3644 (5)0.5479 (5)0.7338 (5)0.0446 (17)
H10G0.29510.51060.74270.067*
H10H0.38720.55710.65870.067*
H10I0.35680.61930.75440.067*
C160.5574 (5)0.5129 (5)0.7790 (5)0.0397 (15)
H10J0.60150.48600.84220.060*
H10K0.56270.59210.76050.060*
H10L0.58310.48060.71870.060*
C170.5507 (5)0.2770 (5)0.8485 (5)0.0354 (14)
H10M0.53860.31570.77510.053*
H10N0.53020.20090.85410.053*
H10O0.62690.28080.86660.053*
C1080.4936 (5)0.2740 (5)1.0319 (5)0.0413 (16)
H10P0.46680.32301.07830.062*
H10Q0.56890.25481.04930.062*
H10R0.45030.20801.04310.062*
C190.1032 (4)0.0557 (4)1.1058 (4)0.0227 (11)
C1100.0514 (5)0.0090 (4)1.2927 (4)0.0314 (13)
H11A0.12660.03361.29750.047*
H11B0.00410.07191.30950.047*
H11C0.03830.03971.34380.047*
C1110.0762 (4)0.1003 (4)1.1676 (4)0.0276 (12)
H11D0.07610.16911.19400.041*
H11E0.13020.05211.20700.041*
H11F0.09360.11421.09110.041*
C1120.2772 (4)0.0107 (5)1.0539 (5)0.0366 (15)
H11G0.27550.02610.98090.055*
H11H0.32930.05941.09680.055*
H11I0.29850.06491.05140.055*
C1130.1397 (5)0.1404 (4)1.1414 (5)0.0348 (14)
H11J0.17470.16711.21030.052*
H11K0.16260.18511.08940.052*
H11L0.06140.14461.15050.052*
C210.5752 (4)0.7498 (4)0.4374 (4)0.0249 (12)
H20A0.58700.75040.36010.030*
H20B0.49730.74020.45260.030*
C220.6390 (4)0.6555 (4)0.5040 (4)0.0247 (12)
H20C0.63530.66170.58060.030*
H20D0.60580.58590.49630.030*
C230.7563 (4)0.6550 (4)0.4692 (4)0.0238 (12)
H20E0.76120.63340.39810.029*
H20F0.78560.72910.46260.029*
C240.9108 (4)0.6078 (4)0.5882 (4)0.0261 (12)
C250.8597 (5)0.5110 (5)0.7638 (5)0.0446 (16)
H20G0.78770.52490.73260.067*
H20H0.86410.54160.82930.067*
H20I0.87320.43250.78090.067*
C261.0505 (5)0.5475 (5)0.7224 (5)0.0466 (17)
H20J1.09800.58420.66560.070*
H20K1.06880.46990.73840.070*
H20L1.05980.57890.78700.070*
C271.0312 (5)0.7613 (5)0.5755 (6)0.0486 (18)
H20M1.01780.74870.65290.073*
H20N1.00500.83400.54310.073*
H20O1.10860.75590.56210.073*
C280.9859 (4)0.6868 (5)0.4150 (4)0.0323 (13)
H20P0.94470.62850.39290.048*
H20Q1.06200.67900.39680.048*
H20R0.95850.75730.37780.048*
C290.6058 (4)0.9482 (4)0.3946 (4)0.0204 (11)
C2100.7843 (4)0.9973 (5)0.4470 (4)0.0317 (13)
H21B0.79260.91820.46490.048*
H21C0.79171.02820.51210.048*
H21D0.83981.02710.39510.048*
C2110.6541 (5)1.1411 (4)0.3695 (4)0.0325 (14)
H21E0.58131.15040.33960.049*
H21F0.70601.17450.31540.049*
H21G0.65831.17590.43240.049*
C2120.5470 (5)1.0306 (4)0.2144 (4)0.0304 (13)
H21H0.62161.05560.20900.046*
H21I0.49801.09350.20320.046*
H21J0.53380.98620.15980.046*
C2130.4196 (4)0.9226 (4)0.3411 (4)0.0266 (12)
H21K0.41590.88070.41420.040*
H21L0.40300.87530.28990.040*
H21M0.36740.98270.33310.040*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0295 (3)0.0298 (3)0.0484 (4)0.0070 (2)0.0001 (3)0.0160 (3)
Br20.0485 (4)0.0283 (3)0.0206 (3)0.0009 (3)0.0074 (3)0.0012 (2)
Br30.0485 (4)0.0341 (3)0.0176 (3)0.0001 (3)0.0074 (3)0.0018 (2)
Br40.0281 (3)0.0258 (3)0.0399 (4)0.0061 (2)0.0014 (3)0.0080 (2)
N110.028 (2)0.015 (2)0.025 (2)0.0011 (19)0.007 (2)0.0010 (18)
N120.028 (3)0.031 (3)0.025 (3)0.005 (2)0.009 (2)0.003 (2)
N130.024 (2)0.028 (2)0.026 (3)0.003 (2)0.003 (2)0.002 (2)
N140.026 (2)0.022 (2)0.018 (2)0.0038 (19)0.0036 (19)0.0019 (18)
N150.028 (2)0.022 (2)0.015 (2)0.0006 (19)0.0037 (19)0.0007 (18)
N160.028 (2)0.022 (2)0.022 (2)0.0019 (19)0.004 (2)0.0031 (19)
N210.025 (2)0.018 (2)0.034 (3)0.0013 (19)0.004 (2)0.003 (2)
N220.030 (3)0.033 (3)0.030 (3)0.001 (2)0.009 (2)0.009 (2)
N230.026 (3)0.028 (3)0.041 (3)0.005 (2)0.000 (2)0.016 (2)
N240.026 (2)0.028 (2)0.016 (2)0.000 (2)0.0003 (19)0.0012 (19)
N250.031 (3)0.020 (2)0.020 (2)0.003 (2)0.002 (2)0.0021 (19)
N260.026 (2)0.026 (2)0.016 (2)0.0003 (19)0.0019 (19)0.0007 (18)
C110.023 (3)0.021 (3)0.032 (3)0.001 (2)0.003 (2)0.004 (2)
C120.026 (3)0.020 (3)0.029 (3)0.003 (2)0.000 (2)0.005 (2)
C130.025 (3)0.027 (3)0.028 (3)0.003 (2)0.003 (2)0.002 (2)
C140.028 (3)0.023 (3)0.023 (3)0.002 (2)0.000 (2)0.005 (2)
C150.053 (4)0.039 (4)0.034 (4)0.014 (3)0.008 (3)0.014 (3)
C160.047 (4)0.037 (3)0.035 (4)0.011 (3)0.015 (3)0.007 (3)
C170.038 (3)0.034 (3)0.037 (4)0.010 (3)0.001 (3)0.015 (3)
C1080.031 (3)0.059 (4)0.027 (3)0.003 (3)0.008 (3)0.009 (3)
C190.022 (3)0.029 (3)0.016 (3)0.004 (2)0.002 (2)0.000 (2)
C1100.043 (4)0.025 (3)0.024 (3)0.000 (3)0.001 (3)0.001 (2)
C1110.025 (3)0.032 (3)0.025 (3)0.004 (2)0.000 (2)0.001 (2)
C1120.033 (3)0.044 (4)0.029 (3)0.014 (3)0.001 (3)0.004 (3)
C1130.052 (4)0.021 (3)0.031 (3)0.001 (3)0.002 (3)0.005 (2)
C210.022 (3)0.024 (3)0.027 (3)0.004 (2)0.003 (2)0.001 (2)
C220.025 (3)0.027 (3)0.021 (3)0.003 (2)0.002 (2)0.001 (2)
C230.028 (3)0.021 (3)0.019 (3)0.002 (2)0.004 (2)0.008 (2)
C240.029 (3)0.021 (3)0.030 (3)0.006 (2)0.007 (3)0.010 (2)
C250.056 (4)0.044 (4)0.030 (4)0.004 (3)0.003 (3)0.002 (3)
C260.045 (4)0.045 (4)0.052 (4)0.012 (3)0.027 (3)0.015 (3)
C270.038 (4)0.042 (4)0.072 (5)0.008 (3)0.002 (3)0.026 (4)
C280.026 (3)0.039 (3)0.031 (3)0.001 (3)0.001 (3)0.003 (3)
C290.025 (3)0.023 (3)0.013 (3)0.002 (2)0.003 (2)0.003 (2)
C2100.036 (3)0.031 (3)0.029 (3)0.010 (3)0.003 (3)0.004 (3)
C2110.045 (4)0.019 (3)0.033 (3)0.007 (3)0.005 (3)0.001 (2)
C2120.038 (3)0.028 (3)0.022 (3)0.001 (3)0.004 (3)0.004 (2)
C2130.023 (3)0.027 (3)0.028 (3)0.007 (2)0.004 (2)0.002 (2)
Geometric parameters (Å, º) top
N11—C141.333 (6)C17—H10M0.9800
N11—C131.465 (6)C17—H10N0.9800
N11—H110.8800C17—H10O0.9800
N12—C141.342 (6)C108—H10P0.9800
N12—C161.459 (7)C108—H10Q0.9800
N12—C151.470 (7)C108—H10R0.9800
N13—C141.322 (6)C110—H11A0.9800
N13—C1081.432 (7)C110—H11B0.9800
N13—C171.452 (6)C110—H11C0.9800
N14—C191.336 (6)C111—H11D0.9800
N14—C111.475 (6)C111—H11E0.9800
N14—H140.8800C111—H11F0.9800
N15—C191.339 (6)C112—H11G0.9800
N15—C1111.449 (6)C112—H11H0.9800
N15—C1101.468 (7)C112—H11I0.9800
N16—C191.335 (6)C113—H11J0.9800
N16—C1131.460 (6)C113—H11K0.9800
N16—C1121.466 (7)C113—H11L0.9800
N21—C241.326 (7)C21—C221.536 (7)
N21—C231.455 (6)C21—H20A0.9900
N21—H210.8800C21—H20B0.9900
N22—C241.335 (7)C22—C231.521 (7)
N22—C261.447 (7)C22—H20C0.9900
N22—C251.454 (7)C22—H20D0.9900
N23—C241.342 (7)C23—H20E0.9900
N23—C281.435 (7)C23—H20F0.9900
N23—C271.450 (7)C25—H20G0.9800
N24—C291.341 (6)C25—H20H0.9800
N24—C211.477 (6)C25—H20I0.9800
N24—H240.8800C26—H20J0.9800
N25—C291.341 (6)C26—H20K0.9800
N25—C2101.446 (7)C26—H20L0.9800
N25—C2111.471 (6)C27—H20M0.9800
N26—C291.339 (6)C27—H20N0.9800
N26—C2121.451 (6)C27—H20O0.9800
N26—C2131.470 (6)C28—H20P0.9800
C11—C121.516 (7)C28—H20Q0.9800
C11—H10A0.9900C28—H20R0.9800
C11—H10B0.9900C210—H21B0.9800
C12—C131.509 (7)C210—H21C0.9800
C12—H10C0.9900C210—H21D0.9800
C12—H10D0.9900C211—H21E0.9800
C13—H10E0.9900C211—H21F0.9800
C13—H10F0.9900C211—H21G0.9800
C15—H10G0.9800C212—H21H0.9800
C15—H10H0.9800C212—H21I0.9800
C15—H10I0.9800C212—H21J0.9800
C16—H10J0.9800C213—H21K0.9800
C16—H10K0.9800C213—H21L0.9800
C16—H10L0.9800C213—H21M0.9800
C14—N11—C13124.5 (4)N15—C111—H11D109.5
C14—N11—H11117.7N15—C111—H11E109.5
C13—N11—H11117.7H11D—C111—H11E109.5
C14—N12—C16121.5 (5)N15—C111—H11F109.5
C14—N12—C15122.1 (5)H11D—C111—H11F109.5
C16—N12—C15116.0 (5)H11E—C111—H11F109.5
C14—N13—C108123.9 (5)N16—C112—H11G109.5
C14—N13—C17121.4 (4)N16—C112—H11H109.5
C108—N13—C17114.4 (4)H11G—C112—H11H109.5
C19—N14—C11124.7 (4)N16—C112—H11I109.5
C19—N14—H14117.7H11G—C112—H11I109.5
C11—N14—H14117.7H11H—C112—H11I109.5
C19—N15—C111123.1 (4)N16—C113—H11J109.5
C19—N15—C110121.4 (4)N16—C113—H11K109.5
C111—N15—C110115.5 (4)H11J—C113—H11K109.5
C19—N16—C113122.6 (4)N16—C113—H11L109.5
C19—N16—C112121.0 (4)H11J—C113—H11L109.5
C113—N16—C112116.3 (4)H11K—C113—H11L109.5
C24—N21—C23123.2 (4)N24—C21—C22109.7 (4)
C24—N21—H21118.4N24—C21—H20A109.7
C23—N21—H21118.4C22—C21—H20A109.7
C24—N22—C26123.7 (5)N24—C21—H20B109.7
C24—N22—C25120.3 (5)C22—C21—H20B109.7
C26—N22—C25115.7 (5)H20A—C21—H20B108.2
C24—N23—C28121.8 (5)C23—C22—C21111.8 (4)
C24—N23—C27121.1 (5)C23—C22—H20C109.2
C28—N23—C27117.0 (5)C21—C22—H20C109.2
C29—N24—C21123.0 (4)C23—C22—H20D109.2
C29—N24—H24118.5C21—C22—H20D109.2
C21—N24—H24118.5H20C—C22—H20D107.9
C29—N25—C210121.8 (4)N21—C23—C22111.0 (4)
C29—N25—C211121.9 (4)N21—C23—H20E109.4
C210—N25—C211116.1 (4)C22—C23—H20E109.4
C29—N26—C212122.1 (4)N21—C23—H20F109.4
C29—N26—C213121.8 (4)C22—C23—H20F109.4
C212—N26—C213116.1 (4)H20E—C23—H20F108.0
N14—C11—C12110.9 (4)N21—C24—N22120.6 (5)
N14—C11—H10A109.5N21—C24—N23119.2 (5)
C12—C11—H10A109.5N22—C24—N23120.2 (5)
N14—C11—H10B109.5N22—C25—H20G109.5
C12—C11—H10B109.5N22—C25—H20H109.5
H10A—C11—H10B108.0H20G—C25—H20H109.5
C13—C12—C11112.3 (4)N22—C25—H20I109.5
C13—C12—H10C109.1H20G—C25—H20I109.5
C11—C12—H10C109.1H20H—C25—H20I109.5
C13—C12—H10D109.1N22—C26—H20J109.5
C11—C12—H10D109.1N22—C26—H20K109.5
H10C—C12—H10D107.9H20J—C26—H20K109.5
N11—C13—C12110.9 (4)N22—C26—H20L109.5
N11—C13—H10E109.5H20J—C26—H20L109.5
C12—C13—H10E109.5H20K—C26—H20L109.5
N11—C13—H10F109.5N23—C27—H20M109.5
C12—C13—H10F109.5N23—C27—H20N109.5
H10E—C13—H10F108.0H20M—C27—H20N109.5
N13—C14—N11121.7 (5)N23—C27—H20O109.5
N13—C14—N12119.4 (5)H20M—C27—H20O109.5
N11—C14—N12118.8 (5)H20N—C27—H20O109.5
N12—C15—H10G109.5N23—C28—H20P109.5
N12—C15—H10H109.5N23—C28—H20Q109.5
H10G—C15—H10H109.5H20P—C28—H20Q109.5
N12—C15—H10I109.5N23—C28—H20R109.5
H10G—C15—H10I109.5H20P—C28—H20R109.5
H10H—C15—H10I109.5H20Q—C28—H20R109.5
N12—C16—H10J109.5N26—C29—N25120.4 (4)
N12—C16—H10K109.5N26—C29—N24120.4 (5)
H10J—C16—H10K109.5N25—C29—N24119.1 (5)
N12—C16—H10L109.5N25—C210—H21B109.5
H10J—C16—H10L109.5N25—C210—H21C109.5
H10K—C16—H10L109.5H21B—C210—H21C109.5
N13—C17—H10M109.5N25—C210—H21D109.5
N13—C17—H10N109.5H21B—C210—H21D109.5
H10M—C17—H10N109.5H21C—C210—H21D109.5
N13—C17—H10O109.5N25—C211—H21E109.5
H10M—C17—H10O109.5N25—C211—H21F109.5
H10N—C17—H10O109.5H21E—C211—H21F109.5
N13—C108—H10P109.5N25—C211—H21G109.5
N13—C108—H10Q109.5H21E—C211—H21G109.5
H10P—C108—H10Q109.5H21F—C211—H21G109.5
N13—C108—H10R109.5N26—C212—H21H109.5
H10P—C108—H10R109.5N26—C212—H21I109.5
H10Q—C108—H10R109.5H21H—C212—H21I109.5
N16—C19—N14120.0 (5)N26—C212—H21J109.5
N16—C19—N15120.0 (5)H21H—C212—H21J109.5
N14—C19—N15119.9 (5)H21I—C212—H21J109.5
N15—C110—H11A109.5N26—C213—H21K109.5
N15—C110—H11B109.5N26—C213—H21L109.5
H11A—C110—H11B109.5H21K—C213—H21L109.5
N15—C110—H11C109.5N26—C213—H21M109.5
H11A—C110—H11C109.5H21K—C213—H21M109.5
H11B—C110—H11C109.5H21L—C213—H21M109.5
C19—N14—C11—C12149.9 (5)C29—N24—C21—C22151.6 (5)
N14—C11—C12—C1362.8 (6)N24—C21—C22—C2369.7 (5)
C14—N11—C13—C12137.5 (5)C24—N21—C23—C22128.9 (5)
C11—C12—C13—N11173.4 (4)C21—C22—C23—N21168.3 (4)
C108—N13—C14—N1128.2 (8)C23—N21—C24—N22148.8 (5)
C17—N13—C14—N11144.8 (5)C23—N21—C24—N2333.4 (7)
C108—N13—C14—N12149.7 (5)C26—N22—C24—N21151.5 (5)
C17—N13—C14—N1237.3 (8)C25—N22—C24—N2121.9 (8)
C13—N11—C14—N1327.4 (8)C26—N22—C24—N2326.3 (8)
C13—N11—C14—N12154.7 (5)C25—N22—C24—N23160.3 (5)
C16—N12—C14—N1330.8 (8)C28—N23—C24—N2134.2 (7)
C15—N12—C14—N13155.8 (5)C27—N23—C24—N21141.5 (5)
C16—N12—C14—N11147.2 (5)C28—N23—C24—N22143.7 (5)
C15—N12—C14—N1126.3 (8)C27—N23—C24—N2240.6 (7)
C113—N16—C19—N14148.1 (5)C212—N26—C29—N2534.1 (7)
C112—N16—C19—N1428.6 (7)C213—N26—C29—N25145.2 (5)
C113—N16—C19—N1530.6 (8)C212—N26—C29—N24146.3 (5)
C112—N16—C19—N15152.6 (5)C213—N26—C29—N2434.4 (7)
C11—N14—C19—N16150.9 (5)C210—N25—C29—N26155.0 (5)
C11—N14—C19—N1530.4 (7)C211—N25—C29—N2629.9 (7)
C111—N15—C19—N16146.1 (5)C210—N25—C29—N2425.4 (7)
C110—N15—C19—N1635.4 (7)C211—N25—C29—N24149.7 (5)
C111—N15—C19—N1432.7 (7)C21—N24—C29—N2631.1 (7)
C110—N15—C19—N14145.8 (5)C21—N24—C29—N25149.2 (5)
(II) 2,2-(propane-1,3-diyl)bis(1,1,3,3-tetramethylguanidinium) tetraphenylborate chloride top
Crystal data top
C13H32N62+·BC24H20·ClF(000) = 1352
Mr = 627.11Dx = 1.175 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 17.5770 (8) ÅCell parameters from 2888 reflections
b = 9.3797 (4) Åθ = 2.4–18.6°
c = 22.4953 (10) ŵ = 0.14 mm1
β = 107.034 (1)°T = 150 K
V = 3546.0 (3) Å3Prism, colourless
Z = 40.20 × 0.20 × 0.15 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
7800 independent reflections
Radiation source: sealed tube4307 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.100
ϕ and ω scansθmax = 27.1°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
h = 2222
Tmin = 0.962, Tmax = 0.975k = 1112
39279 measured reflectionsl = 2828
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)] = 0.044Hydrogen site location: difference Fourier map
wR(F2) = 0.072H-atom parameters constrained
S = 0.91 w = 1/[σ2(Fo2) + (0.014P)2]
where P = (Fo2 + 2Fc2)/3
7800 reflections(Δ/σ)max < 0.001
414 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = 0.24 e Å3
Crystal data top
C13H32N62+·BC24H20·ClV = 3546.0 (3) Å3
Mr = 627.11Z = 4
Monoclinic, P21/cMo Kα radiation
a = 17.5770 (8) ŵ = 0.14 mm1
b = 9.3797 (4) ÅT = 150 K
c = 22.4953 (10) Å0.20 × 0.20 × 0.15 mm
β = 107.034 (1)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
7800 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
4307 reflections with I > 2σ(I)
Tmin = 0.962, Tmax = 0.975Rint = 0.100
39279 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.072H-atom parameters constrained
S = 0.91Δρmax = 0.21 e Å3
7800 reflectionsΔρmin = 0.24 e Å3
414 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*/Ueq
N10.42981 (10)0.28118 (18)0.46007 (8)0.0351 (5)
H10.46630.26820.49590.042*
N20.39148 (10)0.46334 (18)0.38800 (8)0.0324 (5)
N30.51865 (11)0.3681 (2)0.41167 (8)0.0349 (5)
N40.27589 (10)0.08128 (17)0.44950 (8)0.0310 (5)
H40.31990.10980.44200.037*
N50.19748 (10)0.17014 (19)0.35619 (8)0.0359 (5)
N60.14914 (10)0.16326 (19)0.44150 (8)0.0385 (5)
C10.28268 (12)0.0262 (2)0.49847 (10)0.0373 (6)
H1A0.28620.02190.53840.045*
H1B0.23480.08760.48760.045*
C20.35624 (12)0.1168 (2)0.50548 (9)0.0365 (6)
H2A0.36240.18260.54100.044*
H2B0.40350.05380.51550.044*
C30.35448 (12)0.2030 (2)0.44868 (10)0.0389 (6)
H3A0.34710.13900.41240.047*
H3B0.30940.27090.43950.047*
C40.44636 (14)0.3709 (2)0.41930 (10)0.0310 (6)
C50.33170 (12)0.5223 (2)0.41415 (10)0.0433 (7)
H5A0.27960.48110.39280.065*
H5B0.32950.62600.40870.065*
H5C0.34570.49930.45850.065*
C60.38698 (12)0.5152 (2)0.32517 (9)0.0406 (6)
H6A0.40520.61430.32770.061*
H6B0.33180.50970.29860.061*
H6C0.42090.45600.30750.061*
C70.55731 (13)0.4953 (2)0.39588 (10)0.0481 (7)
H7A0.55850.48850.35270.072*
H7B0.61180.50180.42360.072*
H7C0.52750.58040.40090.072*
C80.56775 (12)0.2378 (2)0.42332 (10)0.0455 (7)
H8A0.60720.24410.46430.068*
H8B0.59510.22820.39130.068*
H8C0.53360.15460.42210.068*
C90.20744 (13)0.1379 (2)0.41590 (10)0.0313 (6)
C100.14601 (13)0.2857 (2)0.32397 (10)0.0537 (7)
H10A0.13110.34570.35440.080*
H10B0.17450.34330.30100.080*
H10C0.09800.24540.29480.080*
C110.24061 (12)0.0948 (2)0.31912 (9)0.0435 (7)
H11A0.25970.00310.33870.065*
H11B0.20500.07840.27720.065*
H11C0.28610.15250.31660.065*
C120.06523 (12)0.1435 (3)0.40782 (10)0.0612 (8)
H12A0.06040.10530.36630.092*
H12B0.04130.07650.43060.092*
H12C0.03760.23530.40390.092*
C130.16501 (13)0.1997 (2)0.50729 (10)0.0464 (7)
H13A0.22010.23270.52390.070*
H13B0.12860.27550.51160.070*
H13C0.15690.11530.53040.070*
B10.21730 (15)0.3271 (3)0.16740 (11)0.0309 (7)
C210.18802 (13)0.2673 (2)0.09559 (10)0.0330 (6)
C220.12074 (13)0.3196 (2)0.05074 (11)0.0403 (6)
H22A0.09480.40080.06100.048*
C230.08974 (15)0.2601 (3)0.00755 (11)0.0541 (8)
H23A0.04330.29930.03580.065*
C240.12665 (17)0.1432 (3)0.02460 (12)0.0575 (8)
H24A0.10560.10050.06430.069*
C250.19407 (16)0.0902 (3)0.01685 (12)0.0520 (7)
H25A0.22100.01190.00530.062*
C260.22329 (13)0.1497 (2)0.07537 (11)0.0427 (6)
H26A0.26950.10890.10330.051*
C310.30882 (13)0.2744 (2)0.20032 (10)0.0316 (6)
C320.33150 (14)0.1843 (2)0.25210 (10)0.0405 (6)
H32A0.29140.15180.26940.049*
C330.40888 (14)0.1395 (2)0.27968 (10)0.0439 (7)
H33A0.42050.07710.31440.053*
C340.46928 (14)0.1862 (2)0.25633 (11)0.0442 (7)
H34A0.52280.15750.27530.053*
C350.45049 (13)0.2747 (2)0.20524 (11)0.0404 (6)
H35A0.49120.30870.18890.049*
C360.37226 (13)0.3142 (2)0.17769 (10)0.0362 (6)
H36A0.36070.37170.14130.043*
C410.20919 (13)0.5022 (2)0.16739 (9)0.0320 (6)
C420.13468 (14)0.5671 (3)0.15916 (9)0.0394 (6)
H42A0.08990.50810.15670.047*
C430.12370 (15)0.7132 (3)0.15444 (10)0.0481 (7)
H43A0.07200.75170.14830.058*
C440.18657 (17)0.8031 (3)0.15854 (10)0.0511 (8)
H44A0.17860.90320.15420.061*
C450.26113 (16)0.7457 (3)0.16905 (10)0.0462 (7)
H45A0.30580.80630.17360.055*
C460.27127 (14)0.5986 (2)0.17307 (9)0.0369 (6)
H46A0.32350.56170.18010.044*
C510.15780 (13)0.2591 (2)0.20472 (11)0.0367 (6)
C520.16064 (15)0.3079 (3)0.26397 (11)0.0567 (8)
H52A0.19630.38300.28170.068*
C530.11353 (18)0.2513 (3)0.29831 (13)0.0728 (10)
H53A0.11720.28810.33840.087*
C540.06193 (17)0.1428 (3)0.27406 (15)0.0679 (10)
H54A0.02950.10370.29710.081*
C550.05733 (14)0.0907 (3)0.21622 (13)0.0559 (8)
H55A0.02200.01460.19910.067*
C560.10453 (13)0.1495 (2)0.18263 (11)0.0416 (6)
H56A0.09990.11250.14240.050*
Cl10.43748 (3)0.14939 (6)0.41987 (2)0.03828 (16)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0331 (12)0.0424 (13)0.0266 (12)0.0070 (10)0.0040 (9)0.0067 (10)
N20.0349 (12)0.0325 (12)0.0293 (12)0.0054 (10)0.0086 (10)0.0055 (10)
N30.0331 (12)0.0399 (13)0.0330 (12)0.0017 (11)0.0115 (10)0.0043 (10)
N40.0251 (11)0.0365 (12)0.0317 (12)0.0012 (9)0.0090 (9)0.0074 (10)
N50.0339 (12)0.0427 (13)0.0296 (12)0.0061 (10)0.0070 (10)0.0037 (11)
N60.0310 (12)0.0521 (14)0.0332 (12)0.0070 (11)0.0106 (10)0.0006 (11)
C10.0415 (15)0.0382 (16)0.0370 (15)0.0089 (12)0.0188 (13)0.0103 (12)
C20.0404 (15)0.0395 (16)0.0315 (14)0.0093 (12)0.0134 (12)0.0048 (12)
C30.0333 (15)0.0384 (16)0.0424 (16)0.0044 (12)0.0070 (13)0.0076 (13)
C40.0352 (15)0.0315 (15)0.0259 (14)0.0031 (13)0.0084 (12)0.0015 (12)
C50.0495 (17)0.0375 (16)0.0471 (17)0.0114 (13)0.0208 (14)0.0047 (13)
C60.0488 (16)0.0448 (16)0.0268 (14)0.0024 (13)0.0088 (12)0.0095 (12)
C70.0416 (16)0.0597 (18)0.0417 (16)0.0103 (14)0.0101 (13)0.0095 (14)
C80.0397 (16)0.0541 (18)0.0447 (17)0.0131 (14)0.0154 (13)0.0088 (14)
C90.0272 (14)0.0334 (15)0.0333 (15)0.0005 (12)0.0087 (12)0.0005 (12)
C100.0561 (18)0.0546 (18)0.0435 (17)0.0175 (15)0.0040 (14)0.0110 (14)
C110.0447 (16)0.0575 (18)0.0282 (14)0.0009 (13)0.0104 (13)0.0031 (13)
C120.0311 (16)0.091 (2)0.0625 (19)0.0051 (16)0.0146 (14)0.0030 (17)
C130.0542 (17)0.0488 (17)0.0421 (17)0.0106 (13)0.0234 (14)0.0011 (13)
B10.0339 (16)0.0346 (18)0.0266 (16)0.0028 (14)0.0123 (13)0.0014 (13)
C210.0336 (15)0.0344 (15)0.0359 (15)0.0024 (12)0.0180 (12)0.0048 (12)
C220.0403 (16)0.0444 (17)0.0387 (16)0.0044 (13)0.0154 (13)0.0041 (14)
C230.0554 (19)0.066 (2)0.0382 (18)0.0106 (16)0.0090 (15)0.0011 (15)
C240.076 (2)0.064 (2)0.0350 (17)0.0249 (18)0.0209 (16)0.0140 (16)
C250.065 (2)0.0458 (18)0.055 (2)0.0095 (15)0.0320 (17)0.0142 (16)
C260.0469 (17)0.0423 (17)0.0424 (17)0.0001 (14)0.0186 (14)0.0000 (14)
C310.0407 (15)0.0311 (15)0.0268 (14)0.0004 (12)0.0157 (12)0.0028 (11)
C320.0416 (16)0.0446 (17)0.0383 (16)0.0015 (13)0.0165 (13)0.0055 (13)
C330.0522 (17)0.0429 (17)0.0347 (15)0.0121 (15)0.0095 (14)0.0081 (13)
C340.0402 (16)0.0481 (18)0.0419 (17)0.0142 (14)0.0083 (14)0.0044 (14)
C350.0371 (16)0.0465 (17)0.0411 (16)0.0012 (13)0.0167 (13)0.0042 (13)
C360.0410 (15)0.0415 (16)0.0269 (14)0.0047 (13)0.0111 (12)0.0011 (12)
C410.0346 (15)0.0415 (16)0.0205 (13)0.0044 (13)0.0090 (11)0.0032 (12)
C420.0424 (17)0.0472 (17)0.0308 (15)0.0032 (14)0.0140 (13)0.0051 (13)
C430.0549 (19)0.054 (2)0.0373 (16)0.0226 (16)0.0172 (14)0.0001 (15)
C440.082 (2)0.0392 (18)0.0376 (16)0.0151 (17)0.0263 (17)0.0029 (13)
C450.0633 (19)0.0419 (18)0.0390 (17)0.0021 (15)0.0235 (15)0.0019 (14)
C460.0439 (16)0.0381 (16)0.0303 (15)0.0051 (13)0.0135 (12)0.0005 (12)
C510.0366 (15)0.0393 (16)0.0367 (16)0.0102 (13)0.0146 (13)0.0082 (13)
C520.064 (2)0.066 (2)0.0505 (19)0.0014 (16)0.0328 (16)0.0018 (16)
C530.092 (3)0.081 (3)0.067 (2)0.025 (2)0.056 (2)0.016 (2)
C540.061 (2)0.077 (3)0.085 (3)0.0296 (19)0.051 (2)0.045 (2)
C550.0409 (17)0.053 (2)0.077 (2)0.0099 (14)0.0228 (17)0.0283 (17)
C560.0352 (15)0.0437 (17)0.0503 (17)0.0119 (14)0.0194 (13)0.0151 (14)
Cl10.0310 (3)0.0503 (4)0.0335 (3)0.0043 (3)0.0093 (3)0.0010 (3)
Geometric parameters (Å, º) top
N1—C41.338 (2)C13—H13C0.9800
N1—C31.469 (2)B1—C311.638 (3)
N1—H10.8800B1—C211.644 (3)
N2—C41.334 (2)B1—C411.649 (3)
N2—C51.455 (2)B1—C511.649 (3)
N2—C61.475 (2)C21—C221.399 (3)
N3—C41.331 (2)C21—C261.405 (3)
N3—C71.467 (2)C22—C231.382 (3)
N3—C81.474 (2)C22—H22A0.9500
N4—C91.330 (2)C23—C241.385 (3)
N4—C11.472 (2)C23—H23A0.9500
N4—H40.8800C24—C251.369 (3)
N5—C91.338 (2)C24—H24A0.9500
N5—C101.461 (2)C25—C261.383 (3)
N5—C111.463 (2)C25—H25A0.9500
N6—C91.336 (2)C26—H26A0.9500
N6—C121.459 (2)C31—C321.399 (3)
N6—C131.464 (2)C31—C361.405 (3)
C1—C21.517 (2)C32—C331.384 (3)
C1—H1A0.9900C32—H32A0.9500
C1—H1B0.9900C33—C341.386 (3)
C2—C31.504 (2)C33—H33A0.9500
C2—H2A0.9900C34—C351.378 (3)
C2—H2B0.9900C34—H34A0.9500
C3—H3A0.9900C35—C361.383 (3)
C3—H3B0.9900C35—H35A0.9500
C5—H5A0.9800C36—H36A0.9500
C5—H5B0.9800C41—C461.394 (3)
C5—H5C0.9800C41—C421.406 (3)
C6—H6A0.9800C42—C431.384 (3)
C6—H6B0.9800C42—H42A0.9500
C6—H6C0.9800C43—C441.372 (3)
C7—H7A0.9800C43—H43A0.9500
C7—H7B0.9800C44—C451.372 (3)
C7—H7C0.9800C44—H44A0.9500
C8—H8A0.9800C45—C461.391 (3)
C8—H8B0.9800C45—H45A0.9500
C8—H8C0.9800C46—H46A0.9500
C10—H10A0.9800C51—C561.381 (3)
C10—H10B0.9800C51—C521.396 (3)
C10—H10C0.9800C52—C531.392 (3)
C11—H11A0.9800C52—H52A0.9500
C11—H11B0.9800C53—C541.367 (3)
C11—H11C0.9800C53—H53A0.9500
C12—H12A0.9800C54—C551.370 (3)
C12—H12B0.9800C54—H54A0.9500
C12—H12C0.9800C55—C561.390 (3)
C13—H13A0.9800C55—H55A0.9500
C13—H13B0.9800C56—H56A0.9500
C4—N1—C3124.07 (18)N6—C13—H13A109.5
C4—N1—H1118.0N6—C13—H13B109.5
C3—N1—H1118.0H13A—C13—H13B109.5
C4—N2—C5121.97 (18)N6—C13—H13C109.5
C4—N2—C6123.20 (19)H13A—C13—H13C109.5
C5—N2—C6114.82 (17)H13B—C13—H13C109.5
C4—N3—C7122.9 (2)C31—B1—C21108.95 (18)
C4—N3—C8121.63 (19)C31—B1—C41111.97 (19)
C7—N3—C8115.36 (17)C21—B1—C41109.74 (18)
C9—N4—C1124.08 (18)C31—B1—C51109.79 (18)
C9—N4—H4118.0C21—B1—C51107.79 (18)
C1—N4—H4118.0C41—B1—C51108.51 (18)
C9—N5—C10123.09 (19)C22—C21—C26113.7 (2)
C9—N5—C11121.74 (19)C22—C21—B1123.0 (2)
C10—N5—C11115.12 (17)C26—C21—B1123.0 (2)
C9—N6—C12122.68 (19)C23—C22—C21123.9 (2)
C9—N6—C13122.30 (19)C23—C22—H22A118.0
C12—N6—C13114.77 (17)C21—C22—H22A118.0
N4—C1—C2109.97 (17)C22—C23—C24119.7 (2)
N4—C1—H1A109.7C22—C23—H23A120.1
C2—C1—H1A109.7C24—C23—H23A120.1
N4—C1—H1B109.7C25—C24—C23118.8 (2)
C2—C1—H1B109.7C25—C24—H24A120.6
H1A—C1—H1B108.2C23—C24—H24A120.6
C3—C2—C1114.08 (18)C24—C25—C26120.5 (2)
C3—C2—H2A108.7C24—C25—H25A119.7
C1—C2—H2A108.7C26—C25—H25A119.7
C3—C2—H2B108.7C25—C26—C21123.3 (2)
C1—C2—H2B108.7C25—C26—H26A118.3
H2A—C2—H2B107.6C21—C26—H26A118.3
N1—C3—C2109.07 (17)C32—C31—C36113.5 (2)
N1—C3—H3A109.9C32—C31—B1124.1 (2)
C2—C3—H3A109.9C36—C31—B1122.3 (2)
N1—C3—H3B109.9C33—C32—C31124.0 (2)
C2—C3—H3B109.9C33—C32—H32A118.0
H3A—C3—H3B108.3C31—C32—H32A118.0
N3—C4—N2121.0 (2)C32—C33—C34119.7 (2)
N3—C4—N1118.9 (2)C32—C33—H33A120.2
N2—C4—N1120.1 (2)C34—C33—H33A120.2
N2—C5—H5A109.5C35—C34—C33118.9 (2)
N2—C5—H5B109.5C35—C34—H34A120.5
H5A—C5—H5B109.5C33—C34—H34A120.5
N2—C5—H5C109.5C34—C35—C36120.0 (2)
H5A—C5—H5C109.5C34—C35—H35A120.0
H5B—C5—H5C109.5C36—C35—H35A120.0
N2—C6—H6A109.5C35—C36—C31123.8 (2)
N2—C6—H6B109.5C35—C36—H36A118.1
H6A—C6—H6B109.5C31—C36—H36A118.1
N2—C6—H6C109.5C46—C41—C42113.9 (2)
H6A—C6—H6C109.5C46—C41—B1125.5 (2)
H6B—C6—H6C109.5C42—C41—B1120.6 (2)
N3—C7—H7A109.5C43—C42—C41122.8 (2)
N3—C7—H7B109.5C43—C42—H42A118.6
H7A—C7—H7B109.5C41—C42—H42A118.6
N3—C7—H7C109.5C44—C43—C42120.8 (2)
H7A—C7—H7C109.5C44—C43—H43A119.6
H7B—C7—H7C109.5C42—C43—H43A119.6
N3—C8—H8A109.5C43—C44—C45118.7 (2)
N3—C8—H8B109.5C43—C44—H44A120.7
H8A—C8—H8B109.5C45—C44—H44A120.7
N3—C8—H8C109.5C44—C45—C46119.9 (2)
H8A—C8—H8C109.5C44—C45—H45A120.0
H8B—C8—H8C109.5C46—C45—H45A120.0
N4—C9—N6120.5 (2)C45—C46—C41123.7 (2)
N4—C9—N5119.4 (2)C45—C46—H46A118.1
N6—C9—N5120.1 (2)C41—C46—H46A118.1
N5—C10—H10A109.5C56—C51—C52114.7 (2)
N5—C10—H10B109.5C56—C51—B1124.7 (2)
H10A—C10—H10B109.5C52—C51—B1120.6 (2)
N5—C10—H10C109.5C53—C52—C51123.0 (3)
H10A—C10—H10C109.5C53—C52—H52A118.5
H10B—C10—H10C109.5C51—C52—H52A118.5
N5—C11—H11A109.5C54—C53—C52119.7 (3)
N5—C11—H11B109.5C54—C53—H53A120.1
H11A—C11—H11B109.5C52—C53—H53A120.1
N5—C11—H11C109.5C53—C54—C55119.5 (3)
H11A—C11—H11C109.5C53—C54—H54A120.3
H11B—C11—H11C109.5C55—C54—H54A120.3
N6—C12—H12A109.5C54—C55—C56119.8 (3)
N6—C12—H12B109.5C54—C55—H55A120.1
H12A—C12—H12B109.5C56—C55—H55A120.1
N6—C12—H12C109.5C51—C56—C55123.4 (2)
H12A—C12—H12C109.5C51—C56—H56A118.3
H12B—C12—H12C109.5C55—C56—H56A118.3
C9—N4—C1—C2153.0 (2)C51—B1—C31—C320.4 (3)
N4—C1—C2—C363.4 (2)C21—B1—C31—C3661.2 (3)
C4—N1—C3—C2178.05 (19)C41—B1—C31—C3660.4 (3)
C1—C2—C3—N1177.63 (17)C51—B1—C31—C36179.01 (19)
C7—N3—C4—N230.5 (3)C36—C31—C32—C331.1 (3)
C8—N3—C4—N2154.25 (19)B1—C31—C32—C33179.7 (2)
C7—N3—C4—N1148.08 (19)C31—C32—C33—C340.9 (4)
C8—N3—C4—N127.2 (3)C32—C33—C34—C351.1 (3)
C5—N2—C4—N3148.0 (2)C33—C34—C35—C360.8 (3)
C6—N2—C4—N331.2 (3)C34—C35—C36—C313.0 (3)
C5—N2—C4—N130.6 (3)C32—C31—C36—C353.0 (3)
C6—N2—C4—N1150.21 (19)B1—C31—C36—C35178.3 (2)
C3—N1—C4—N3138.4 (2)C31—B1—C41—C4621.6 (3)
C3—N1—C4—N243.0 (3)C21—B1—C41—C4699.5 (2)
C1—N4—C9—N635.6 (3)C51—B1—C41—C46142.9 (2)
C1—N4—C9—N5144.8 (2)C31—B1—C41—C42160.61 (19)
C12—N6—C9—N4143.0 (2)C21—B1—C41—C4278.3 (2)
C13—N6—C9—N430.9 (3)C51—B1—C41—C4239.3 (3)
C12—N6—C9—N537.4 (3)C46—C41—C42—C432.7 (3)
C13—N6—C9—N5148.7 (2)B1—C41—C42—C43175.4 (2)
C10—N5—C9—N4150.6 (2)C41—C42—C43—C440.9 (4)
C11—N5—C9—N426.8 (3)C42—C43—C44—C451.7 (4)
C10—N5—C9—N629.0 (3)C43—C44—C45—C462.3 (3)
C11—N5—C9—N6153.6 (2)C44—C45—C46—C410.4 (4)
C31—B1—C21—C22164.8 (2)C42—C41—C46—C452.0 (3)
C41—B1—C21—C2241.9 (3)B1—C41—C46—C45175.9 (2)
C51—B1—C21—C2276.1 (3)C31—B1—C51—C56106.4 (2)
C31—B1—C21—C2621.9 (3)C21—B1—C51—C5612.2 (3)
C41—B1—C21—C26144.8 (2)C41—B1—C51—C56131.0 (2)
C51—B1—C21—C2697.2 (2)C31—B1—C51—C5271.2 (3)
C26—C21—C22—C231.7 (3)C21—B1—C51—C52170.2 (2)
B1—C21—C22—C23172.2 (2)C41—B1—C51—C5251.4 (3)
C21—C22—C23—C241.1 (4)C56—C51—C52—C530.2 (4)
C22—C23—C24—C250.8 (4)B1—C51—C52—C53178.0 (2)
C23—C24—C25—C262.0 (4)C51—C52—C53—C540.3 (4)
C24—C25—C26—C211.4 (4)C52—C53—C54—C550.1 (4)
C22—C21—C26—C250.5 (3)C53—C54—C55—C560.6 (4)
B1—C21—C26—C25173.4 (2)C52—C51—C56—C550.3 (3)
C21—B1—C31—C32117.4 (2)B1—C51—C56—C55177.4 (2)
C41—B1—C31—C32121.0 (2)C54—C55—C56—C510.7 (4)
(III) 2,2-(propane-1,3-diyl)bis(1,1,3,3-tetramethylguanidinium) tetrachloromercurate top
Crystal data top
(C13H32N6)[HgCl4]F(000) = 1200
Mr = 614.84Dx = 1.772 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 8.3199 (4) ÅCell parameters from 6011 reflections
b = 18.0809 (9) Åθ = 2.5–28.2°
c = 15.8086 (8) ŵ = 7.15 mm1
β = 104.291 (1)°T = 120 K
V = 2304.5 (2) Å3Plate, colourless
Z = 40.45 × 0.20 × 0.08 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
5049 independent reflections
Radiation source: sealed tube4421 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.025
ϕ and ω scansθmax = 27.1°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
h = 1010
Tmin = 0.133, Tmax = 0.563k = 2323
23407 measured reflectionsl = 2020
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)] = 0.028Hydrogen site location: difference Fourier map
wR(F2) = 0.087H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0523P)2 + 4.0796P]
where P = (Fo2 + 2Fc2)/3
5049 reflections(Δ/σ)max = 0.001
225 parametersΔρmax = 0.92 e Å3
0 restraintsΔρmin = 0.55 e Å3
Crystal data top
(C13H32N6)[HgCl4]V = 2304.5 (2) Å3
Mr = 614.84Z = 4
Monoclinic, P21/cMo Kα radiation
a = 8.3199 (4) ŵ = 7.15 mm1
b = 18.0809 (9) ÅT = 120 K
c = 15.8086 (8) Å0.45 × 0.20 × 0.08 mm
β = 104.291 (1)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
5049 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
4421 reflections with I > 2σ(I)
Tmin = 0.133, Tmax = 0.563Rint = 0.025
23407 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0280 restraints
wR(F2) = 0.087H-atom parameters constrained
S = 1.07Δρmax = 0.92 e Å3
5049 reflectionsΔρmin = 0.55 e Å3
225 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*/Ueq
Hg11.036601 (19)0.373597 (8)0.214262 (10)0.02617 (7)
Cl10.86299 (14)0.48923 (6)0.18001 (7)0.0339 (2)
Cl21.14518 (12)0.37532 (5)0.37664 (6)0.0248 (2)
Cl31.22766 (13)0.37896 (5)0.11823 (7)0.0261 (2)
Cl40.86451 (13)0.25760 (5)0.17265 (7)0.0289 (2)
N10.6484 (4)0.23573 (17)0.3237 (2)0.0248 (7)
H10.70730.23130.28480.030*
N20.5293 (5)0.1627 (2)0.4125 (3)0.0300 (8)
N30.8064 (4)0.1476 (2)0.4122 (2)0.0262 (7)
N40.6288 (4)0.50641 (18)0.3130 (2)0.0266 (7)
H40.70610.50760.28380.032*
N50.7383 (5)0.61109 (19)0.3881 (2)0.0285 (8)
N60.4587 (4)0.58261 (19)0.3707 (2)0.0263 (7)
C10.5328 (5)0.4381 (2)0.3095 (3)0.0265 (8)
H1A0.45120.43440.25230.032*
H1B0.47120.43900.35560.032*
C20.6468 (5)0.37128 (19)0.3224 (3)0.0273 (9)
H2A0.72820.37450.37970.033*
H2B0.70840.37000.27630.033*
C30.5433 (5)0.3014 (2)0.3184 (3)0.0273 (9)
H3A0.48860.30120.36740.033*
H3B0.45590.30050.26310.033*
C40.6616 (5)0.1820 (2)0.3832 (3)0.0212 (7)
C50.3603 (5)0.1678 (3)0.3563 (4)0.0410 (12)
H5A0.30470.21130.37280.061*
H5B0.29810.12310.36330.061*
H5C0.36540.17240.29520.061*
C60.5423 (8)0.1371 (3)0.5008 (4)0.0486 (14)
H6A0.51470.08430.49970.073*
H6B0.46500.16500.52640.073*
H6C0.65580.14460.53590.073*
C70.9620 (5)0.1810 (3)0.4051 (3)0.0385 (11)
H7A0.98850.16420.35110.058*
H7B1.05110.16630.45530.058*
H7C0.95100.23500.40400.058*
C80.8199 (6)0.0695 (2)0.4390 (3)0.0366 (10)
H8A0.86190.06640.50250.055*
H8B0.89640.04390.41070.055*
H8C0.71030.04620.42170.055*
C90.6074 (5)0.5668 (2)0.3570 (3)0.0229 (8)
C100.9072 (6)0.5854 (3)0.4011 (4)0.0406 (11)
H10A0.91020.53140.40750.061*
H10B0.97650.60800.45400.061*
H10C0.94950.59920.35070.061*
C110.7193 (7)0.6914 (2)0.3980 (3)0.0404 (11)
H11A0.60410.70560.37160.061*
H11B0.79330.71780.36880.061*
H11C0.74770.70410.46020.061*
C120.3039 (5)0.5650 (2)0.3066 (3)0.0306 (9)
H12A0.32860.54990.25160.046*
H12B0.23220.60880.29660.046*
H12C0.24740.52460.32880.046*
C130.4409 (7)0.6150 (3)0.4525 (3)0.0385 (11)
H13A0.54880.61500.49510.058*
H13B0.36160.58580.47520.058*
H13C0.40050.66590.44210.058*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Hg10.02870 (11)0.02320 (10)0.02870 (11)0.00034 (5)0.01107 (7)0.00050 (6)
Cl10.0446 (6)0.0258 (5)0.0391 (6)0.0137 (4)0.0256 (5)0.0080 (4)
Cl20.0216 (4)0.0353 (5)0.0152 (4)0.0062 (3)0.0005 (3)0.0059 (3)
Cl30.0270 (5)0.0277 (5)0.0267 (5)0.0012 (4)0.0124 (4)0.0012 (4)
Cl40.0346 (5)0.0182 (4)0.0397 (6)0.0100 (4)0.0201 (4)0.0065 (4)
N10.0264 (17)0.0196 (15)0.0316 (18)0.0034 (13)0.0133 (14)0.0028 (14)
N20.0288 (18)0.0281 (18)0.038 (2)0.0035 (14)0.0182 (16)0.0002 (15)
N30.0267 (18)0.0230 (15)0.0297 (18)0.0013 (14)0.0084 (14)0.0049 (14)
N40.0312 (18)0.0185 (15)0.0354 (19)0.0042 (13)0.0182 (15)0.0038 (14)
N50.033 (2)0.0211 (16)0.0322 (19)0.0057 (14)0.0096 (16)0.0048 (14)
N60.0275 (18)0.0264 (17)0.0249 (17)0.0045 (14)0.0063 (14)0.0031 (14)
C10.025 (2)0.0179 (18)0.036 (2)0.0026 (15)0.0076 (17)0.0002 (16)
C20.024 (2)0.0205 (19)0.039 (2)0.0010 (14)0.0113 (18)0.0018 (16)
C30.022 (2)0.0161 (17)0.044 (2)0.0026 (14)0.0095 (17)0.0015 (17)
C40.0253 (19)0.0159 (16)0.0242 (19)0.0034 (14)0.0094 (15)0.0046 (14)
C50.024 (2)0.030 (2)0.071 (4)0.0076 (17)0.015 (2)0.006 (2)
C60.061 (4)0.049 (3)0.048 (3)0.002 (2)0.037 (3)0.005 (2)
C70.023 (2)0.044 (3)0.046 (3)0.0007 (19)0.0041 (19)0.012 (2)
C80.046 (3)0.029 (2)0.036 (2)0.0087 (19)0.013 (2)0.0085 (19)
C90.029 (2)0.0195 (17)0.0208 (18)0.0003 (15)0.0083 (15)0.0020 (15)
C100.030 (2)0.040 (3)0.053 (3)0.006 (2)0.012 (2)0.008 (2)
C110.057 (3)0.021 (2)0.041 (3)0.006 (2)0.009 (2)0.0041 (19)
C120.029 (2)0.028 (2)0.032 (2)0.0060 (17)0.0023 (18)0.0005 (18)
C130.039 (3)0.048 (3)0.029 (2)0.011 (2)0.010 (2)0.008 (2)
Geometric parameters (Å, º) top
Hg1—Cl32.4561 (10)C2—H2B0.9900
Hg1—Cl22.5023 (9)C3—H3A0.9900
Hg1—Cl12.5228 (10)C3—H3B0.9900
Hg1—Cl42.5331 (9)C5—H5A0.9800
N1—C41.338 (5)C5—H5B0.9800
N1—C31.464 (5)C5—H5C0.9800
N1—H10.8800C6—H6A0.9800
N2—C41.341 (5)C6—H6B0.9800
N2—C61.449 (7)C6—H6C0.9800
N2—C51.469 (6)C7—H7A0.9800
N3—C41.333 (5)C7—H7B0.9800
N3—C71.458 (6)C7—H7C0.9800
N3—C81.470 (5)C8—H8A0.9800
N4—C91.330 (5)C8—H8B0.9800
N4—C11.465 (5)C8—H8C0.9800
N4—H40.8800C10—H10A0.9800
N5—C91.344 (5)C10—H10B0.9800
N5—C101.446 (6)C10—H10C0.9800
N5—C111.473 (5)C11—H11A0.9800
N6—C91.338 (5)C11—H11B0.9800
N6—C131.460 (6)C11—H11C0.9800
N6—C121.463 (5)C12—H12A0.9800
C1—C21.517 (5)C12—H12B0.9800
C1—H1A0.9900C12—H12C0.9800
C1—H1B0.9900C13—H13A0.9800
C2—C31.522 (5)C13—H13B0.9800
C2—H2A0.9900C13—H13C0.9800
Cl3—Hg1—Cl2120.58 (3)N2—C5—H5C109.5
Cl3—Hg1—Cl1104.96 (3)H5A—C5—H5C109.5
Cl2—Hg1—Cl1104.62 (3)H5B—C5—H5C109.5
Cl3—Hg1—Cl4106.43 (3)N2—C6—H6A109.5
Cl2—Hg1—Cl4108.33 (3)N2—C6—H6B109.5
Cl1—Hg1—Cl4111.93 (4)H6A—C6—H6B109.5
C4—N1—C3125.0 (3)N2—C6—H6C109.5
C4—N1—H1117.5H6A—C6—H6C109.5
C3—N1—H1117.5H6B—C6—H6C109.5
C4—N2—C6122.9 (4)N3—C7—H7A109.5
C4—N2—C5121.3 (4)N3—C7—H7B109.5
C6—N2—C5115.8 (4)H7A—C7—H7B109.5
C4—N3—C7121.7 (3)N3—C7—H7C109.5
C4—N3—C8123.0 (4)H7A—C7—H7C109.5
C7—N3—C8114.5 (4)H7B—C7—H7C109.5
C9—N4—C1124.7 (3)N3—C8—H8A109.5
C9—N4—H4117.6N3—C8—H8B109.5
C1—N4—H4117.6H8A—C8—H8B109.5
C9—N5—C10122.1 (4)N3—C8—H8C109.5
C9—N5—C11121.8 (4)H8A—C8—H8C109.5
C10—N5—C11115.4 (4)H8B—C8—H8C109.5
C9—N6—C13121.9 (4)N4—C9—N6120.5 (4)
C9—N6—C12122.2 (4)N4—C9—N5118.7 (4)
C13—N6—C12115.8 (4)N6—C9—N5120.8 (4)
N4—C1—C2110.5 (3)N5—C10—H10A109.5
N4—C1—H1A109.6N5—C10—H10B109.5
C2—C1—H1A109.6H10A—C10—H10B109.5
N4—C1—H1B109.6N5—C10—H10C109.5
C2—C1—H1B109.6H10A—C10—H10C109.5
H1A—C1—H1B108.1H10B—C10—H10C109.5
C1—C2—C3109.1 (3)N5—C11—H11A109.5
C1—C2—H2A109.9N5—C11—H11B109.5
C3—C2—H2A109.9H11A—C11—H11B109.5
C1—C2—H2B109.9N5—C11—H11C109.5
C3—C2—H2B109.9H11A—C11—H11C109.5
H2A—C2—H2B108.3H11B—C11—H11C109.5
N1—C3—C2110.3 (3)N6—C12—H12A109.5
N1—C3—H3A109.6N6—C12—H12B109.5
C2—C3—H3A109.6H12A—C12—H12B109.5
N1—C3—H3B109.6N6—C12—H12C109.5
C2—C3—H3B109.6H12A—C12—H12C109.5
H3A—C3—H3B108.1H12B—C12—H12C109.5
N3—C4—N1119.4 (3)N6—C13—H13A109.5
N3—C4—N2120.6 (4)N6—C13—H13B109.5
N1—C4—N2120.0 (4)H13A—C13—H13B109.5
N2—C5—H5A109.5N6—C13—H13C109.5
N2—C5—H5B109.5H13A—C13—H13C109.5
H5A—C5—H5B109.5H13B—C13—H13C109.5
C9—N4—C1—C2134.8 (4)C6—N2—C4—N1147.2 (4)
N4—C1—C2—C3180.0 (3)C5—N2—C4—N131.7 (6)
C4—N1—C3—C2123.8 (4)C1—N4—C9—N628.8 (6)
C1—C2—C3—N1175.5 (3)C1—N4—C9—N5150.6 (4)
C7—N3—C4—N121.0 (6)C13—N6—C9—N4142.5 (4)
C8—N3—C4—N1148.1 (4)C12—N6—C9—N434.2 (6)
C7—N3—C4—N2159.7 (4)C13—N6—C9—N536.9 (6)
C8—N3—C4—N231.3 (6)C12—N6—C9—N5146.4 (4)
C3—N1—C4—N3146.2 (4)C10—N5—C9—N420.6 (6)
C3—N1—C4—N234.5 (6)C11—N5—C9—N4149.7 (4)
C6—N2—C4—N333.4 (6)C10—N5—C9—N6158.8 (4)
C5—N2—C4—N3147.7 (4)C11—N5—C9—N630.9 (6)
(IV) 2,2-(propane-1,3-diyl)bis(1,1,3,3-tetramethylguanidinium) bis(trifluoromethanesulfonate) top
Crystal data top
C13H32N62+·2CF3O3SZ = 2
Mr = 570.59F(000) = 596
Triclinic, P1Dx = 1.468 Mg m3
a = 8.8771 (7) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.3802 (10) ÅCell parameters from 3136 reflections
c = 12.5704 (10) Åθ = 2.7–28.2°
α = 108.939 (2)°µ = 0.29 mm1
β = 91.478 (2)°T = 120 K
γ = 97.775 (2)°Prism, colourless
V = 1291.10 (18) Å30.40 × 0.20 × 0.20 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
5165 independent reflections
Radiation source: sealed tube4404 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.012
ϕ and ω scansθmax = 26.4°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
h = 1010
Tmin = 0.893, Tmax = 0.944k = 1513
7636 measured reflectionsl = 1515
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)] = 0.046Hydrogen site location: difference Fourier map
wR(F2) = 0.121H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0574P)2 + 0.8973P]
where P = (Fo2 + 2Fc2)/3
5165 reflections(Δ/σ)max = 0.001
337 parametersΔρmax = 0.76 e Å3
30 restraintsΔρmin = 0.51 e Å3
Crystal data top
C13H32N62+·2CF3O3Sγ = 97.775 (2)°
Mr = 570.59V = 1291.10 (18) Å3
Triclinic, P1Z = 2
a = 8.8771 (7) ÅMo Kα radiation
b = 12.3802 (10) ŵ = 0.29 mm1
c = 12.5704 (10) ÅT = 120 K
α = 108.939 (2)°0.40 × 0.20 × 0.20 mm
β = 91.478 (2)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
5165 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
4404 reflections with I > 2σ(I)
Tmin = 0.893, Tmax = 0.944Rint = 0.012
7636 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.04630 restraints
wR(F2) = 0.121H-atom parameters constrained
S = 1.03Δρmax = 0.76 e Å3
5165 reflectionsΔρmin = 0.51 e Å3
337 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)
N10.34134 (19)0.72040 (15)1.04886 (14)0.0264 (4)
H10.43920.73411.03970.032*
N20.3600 (2)0.89892 (15)1.18526 (15)0.0314 (4)
N30.1719 (2)0.75124 (15)1.18943 (14)0.0262 (4)
N40.2747 (2)0.50063 (14)0.64499 (14)0.0253 (4)
H40.29400.56110.62260.030*
N50.3539 (2)0.32301 (15)0.61862 (14)0.0263 (4)
N60.29202 (19)0.37788 (15)0.46531 (14)0.0256 (4)
C10.2109 (2)0.51825 (18)0.75437 (16)0.0253 (4)
H1A0.21140.44780.77530.030*
H1B0.10370.53090.74830.030*
C20.3003 (2)0.62071 (18)0.84611 (16)0.0264 (4)
H2A0.28430.69310.83290.032*
H2B0.41040.61520.84350.032*
C30.2498 (2)0.62388 (18)0.96128 (17)0.0261 (4)
H3A0.14070.63280.96520.031*
H3B0.26200.55040.97350.031*
C40.2902 (2)0.78947 (17)1.14127 (16)0.0241 (4)
C50.3764 (3)0.9599 (2)1.30678 (19)0.0427 (6)
H5A0.31121.02041.32550.064*
H5B0.48290.99511.32970.064*
H5C0.34600.90521.34670.064*
C60.4434 (3)0.9577 (2)1.1161 (2)0.0425 (6)
H6A0.55070.94721.11880.064*
H6B0.43611.04031.14520.064*
H6C0.39940.92511.03800.064*
C70.0641 (3)0.8258 (2)1.24782 (19)0.0369 (5)
H7A0.07730.83951.32900.055*
H7B0.04030.78801.21970.055*
H7C0.08300.89961.23380.055*
C80.1391 (3)0.63118 (19)1.18482 (18)0.0297 (5)
H8A0.05330.59101.12920.045*
H8B0.11280.62831.25920.045*
H8C0.22920.59351.16300.045*
C90.3058 (2)0.40031 (17)0.57669 (16)0.0227 (4)
C100.3075 (3)0.19908 (18)0.5662 (2)0.0342 (5)
H10A0.22690.18450.50620.051*
H10B0.26910.16590.62300.051*
H10C0.39520.16330.53390.051*
C110.4550 (3)0.3572 (2)0.72119 (19)0.0358 (5)
H11A0.49250.44030.74430.054*
H11B0.54150.31430.70680.054*
H11C0.39890.34020.78140.054*
C120.3864 (3)0.3047 (2)0.38821 (19)0.0348 (5)
H12A0.46880.28880.43170.052*
H12B0.43010.34440.33770.052*
H12C0.32350.23170.34360.052*
C130.1949 (3)0.4367 (2)0.41384 (18)0.0353 (5)
H13A0.11320.46150.46290.053*
H13B0.15020.38360.34030.053*
H13C0.25610.50430.40390.053*
S10.76527 (6)0.69756 (5)0.96309 (5)0.03179 (15)
C1000.8910 (3)0.8115 (3)0.9361 (3)0.0486 (7)
F110.9936 (2)0.7646 (2)0.8635 (2)0.0868 (7)
F120.9659 (3)0.88298 (18)1.02531 (18)0.0987 (9)
F130.8205 (2)0.86858 (16)0.88394 (17)0.0724 (5)
O1110.6642 (2)0.7586 (2)1.0382 (2)0.0607 (8)0.919 (4)
O1210.6959 (2)0.62478 (17)0.85468 (16)0.0489 (6)0.919 (4)
O1310.8665 (2)0.64456 (18)1.01468 (19)0.0484 (6)0.919 (4)
O1120.6299 (18)0.7489 (18)0.9535 (17)0.044 (6)*0.081 (4)
O1220.816 (2)0.6321 (16)0.8617 (11)0.041 (6)*0.081 (4)
O1320.803 (2)0.6881 (17)1.0651 (11)0.033 (5)*0.081 (4)
S20.17814 (6)0.76156 (5)0.53805 (5)0.03020 (15)
C2000.1155 (3)0.8926 (2)0.6276 (2)0.0350 (5)
F210.2206 (2)0.95589 (15)0.70753 (15)0.0679 (5)
F220.0816 (2)0.95771 (13)0.56757 (15)0.0602 (5)
F230.00844 (18)0.86972 (14)0.67687 (14)0.0552 (4)
O210.3050 (2)0.80330 (19)0.48704 (17)0.0551 (5)
O220.2170 (2)0.70685 (16)0.61753 (15)0.0500 (5)
O230.0464 (2)0.70365 (15)0.46297 (14)0.0418 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0222 (9)0.0289 (9)0.0235 (9)0.0023 (7)0.0040 (7)0.0028 (7)
N20.0416 (11)0.0242 (9)0.0255 (9)0.0017 (8)0.0036 (8)0.0054 (7)
N30.0279 (9)0.0284 (9)0.0218 (8)0.0080 (7)0.0055 (7)0.0058 (7)
N40.0333 (10)0.0222 (8)0.0204 (8)0.0053 (7)0.0035 (7)0.0065 (7)
N50.0291 (9)0.0239 (9)0.0249 (9)0.0053 (7)0.0025 (7)0.0066 (7)
N60.0270 (9)0.0295 (9)0.0200 (8)0.0082 (7)0.0022 (7)0.0062 (7)
C10.0242 (10)0.0294 (11)0.0221 (10)0.0051 (8)0.0051 (8)0.0074 (8)
C20.0283 (11)0.0269 (10)0.0222 (10)0.0041 (8)0.0048 (8)0.0055 (8)
C30.0275 (11)0.0263 (10)0.0215 (10)0.0031 (8)0.0036 (8)0.0041 (8)
C40.0271 (10)0.0260 (10)0.0201 (9)0.0077 (8)0.0003 (8)0.0073 (8)
C50.0593 (16)0.0305 (12)0.0283 (12)0.0007 (11)0.0005 (11)0.0012 (10)
C60.0558 (16)0.0298 (12)0.0420 (14)0.0001 (11)0.0097 (12)0.0139 (11)
C70.0371 (13)0.0464 (14)0.0276 (11)0.0174 (11)0.0101 (10)0.0079 (10)
C80.0336 (12)0.0321 (11)0.0231 (10)0.0004 (9)0.0026 (8)0.0107 (9)
C90.0196 (9)0.0239 (10)0.0226 (10)0.0011 (7)0.0005 (7)0.0060 (8)
C100.0390 (13)0.0241 (11)0.0375 (12)0.0043 (9)0.0017 (10)0.0082 (9)
C110.0397 (13)0.0373 (13)0.0306 (11)0.0102 (10)0.0082 (10)0.0105 (10)
C120.0366 (12)0.0409 (13)0.0275 (11)0.0131 (10)0.0103 (9)0.0086 (10)
C130.0448 (13)0.0416 (13)0.0228 (10)0.0167 (10)0.0010 (9)0.0112 (10)
S10.0251 (3)0.0356 (3)0.0316 (3)0.0029 (2)0.0009 (2)0.0077 (2)
C1000.0388 (14)0.0597 (17)0.0605 (17)0.0046 (12)0.0004 (13)0.0392 (15)
F110.0624 (12)0.1195 (18)0.1062 (17)0.0239 (12)0.0419 (12)0.0685 (15)
F120.1292 (19)0.0778 (14)0.0791 (14)0.0664 (14)0.0509 (13)0.0495 (12)
F130.0958 (14)0.0634 (11)0.0745 (12)0.0187 (10)0.0074 (11)0.0436 (10)
O1110.0406 (12)0.0610 (14)0.0651 (17)0.0042 (10)0.0237 (11)0.0003 (12)
O1210.0482 (14)0.0470 (12)0.0416 (11)0.0025 (9)0.0093 (9)0.0041 (9)
O1310.0465 (12)0.0444 (12)0.0587 (14)0.0010 (9)0.0132 (10)0.0272 (11)
S20.0341 (3)0.0321 (3)0.0294 (3)0.0132 (2)0.0067 (2)0.0135 (2)
C2000.0383 (13)0.0298 (12)0.0367 (12)0.0075 (9)0.0005 (10)0.0098 (10)
F210.0664 (11)0.0522 (10)0.0622 (11)0.0032 (8)0.0204 (9)0.0078 (8)
F220.0847 (12)0.0393 (9)0.0687 (11)0.0252 (8)0.0038 (9)0.0280 (8)
F230.0544 (10)0.0588 (10)0.0526 (9)0.0204 (8)0.0262 (8)0.0125 (8)
O210.0384 (10)0.0788 (14)0.0585 (12)0.0166 (9)0.0200 (9)0.0327 (11)
O220.0749 (13)0.0427 (10)0.0431 (10)0.0295 (9)0.0026 (9)0.0209 (8)
O230.0498 (10)0.0390 (9)0.0320 (9)0.0042 (8)0.0006 (7)0.0067 (7)
Geometric parameters (Å, º) top
N1—C41.332 (3)C7—H7C0.9800
N1—C31.462 (3)C8—H8A0.9800
N1—H10.8800C8—H8B0.9800
N2—C41.340 (3)C8—H8C0.9800
N2—C61.460 (3)C10—H10A0.9800
N2—C51.461 (3)C10—H10B0.9800
N3—C41.333 (3)C10—H10C0.9800
N3—C81.457 (3)C11—H11A0.9800
N3—C71.463 (3)C11—H11B0.9800
N4—C91.330 (3)C11—H11C0.9800
N4—C11.462 (3)C12—H12A0.9800
N4—H40.8800C12—H12B0.9800
N5—C91.343 (3)C12—H12C0.9800
N5—C101.455 (3)C13—H13A0.9800
N5—C111.459 (3)C13—H13B0.9800
N6—C91.335 (3)C13—H13C0.9800
N6—C121.463 (3)S1—O1321.362 (10)
N6—C131.462 (3)S1—O1221.394 (11)
C1—C21.516 (3)S1—O1111.425 (2)
C1—H1A0.9900S1—O1211.4344 (19)
C1—H1B0.9900S1—O1311.437 (2)
C2—C31.517 (3)S1—O1121.453 (11)
C2—H2A0.9900S1—C1001.805 (3)
C2—H2B0.9900C100—F121.281 (3)
C3—H3A0.9900C100—F131.311 (3)
C3—H3B0.9900C100—F111.357 (4)
C5—H5A0.9800S2—O211.4291 (19)
C5—H5B0.9800S2—O231.4317 (18)
C5—H5C0.9800S2—O221.4354 (17)
C6—H6A0.9800S2—C2001.816 (2)
C6—H6B0.9800C200—F231.319 (3)
C6—H6C0.9800C200—F211.317 (3)
C7—H7A0.9800C200—F221.327 (3)
C7—H7B0.9800
C4—N1—C3125.94 (18)N3—C8—H8C109.5
C4—N1—H1117.0H8A—C8—H8C109.5
C3—N1—H1117.0H8B—C8—H8C109.5
C4—N2—C6121.53 (18)N4—C9—N6119.29 (18)
C4—N2—C5121.91 (19)N4—C9—N5120.75 (18)
C6—N2—C5115.95 (19)N6—C9—N5119.94 (18)
C4—N3—C8122.04 (17)N5—C10—H10A109.5
C4—N3—C7122.51 (18)N5—C10—H10B109.5
C8—N3—C7115.43 (18)H10A—C10—H10B109.5
C9—N4—C1125.10 (17)N5—C10—H10C109.5
C9—N4—H4117.4H10A—C10—H10C109.5
C1—N4—H4117.4H10B—C10—H10C109.5
C9—N5—C10122.53 (17)N5—C11—H11A109.5
C9—N5—C11122.43 (17)N5—C11—H11B109.5
C10—N5—C11115.04 (17)H11A—C11—H11B109.5
C9—N6—C12122.56 (18)N5—C11—H11C109.5
C9—N6—C13121.78 (17)H11A—C11—H11C109.5
C12—N6—C13115.24 (17)H11B—C11—H11C109.5
N4—C1—C2111.93 (16)N6—C12—H12A109.5
N4—C1—H1A109.2N6—C12—H12B109.5
C2—C1—H1A109.2H12A—C12—H12B109.5
N4—C1—H1B109.2N6—C12—H12C109.5
C2—C1—H1B109.2H12A—C12—H12C109.5
H1A—C1—H1B107.9H12B—C12—H12C109.5
C1—C2—C3110.61 (17)N6—C13—H13A109.5
C1—C2—H2A109.5N6—C13—H13B109.5
C3—C2—H2A109.5H13A—C13—H13B109.5
C1—C2—H2B109.5N6—C13—H13C109.5
C3—C2—H2B109.5H13A—C13—H13C109.5
H2A—C2—H2B108.1H13B—C13—H13C109.5
N1—C3—C2109.80 (17)O132—S1—O122124.0 (9)
N1—C3—H3A109.7O111—S1—O121115.11 (13)
C2—C3—H3A109.7O111—S1—O131113.82 (15)
N1—C3—H3B109.7O121—S1—O131114.34 (13)
C2—C3—H3B109.7O132—S1—O112117.2 (9)
H3A—C3—H3B108.2O122—S1—O112115.8 (9)
N1—C4—N3121.08 (19)O132—S1—C100111.7 (8)
N1—C4—N2118.62 (19)O122—S1—C10081.7 (9)
N3—C4—N2120.30 (19)O111—S1—C100103.08 (14)
N2—C5—H5A109.5O121—S1—C100105.32 (13)
N2—C5—H5B109.5O131—S1—C100103.26 (12)
H5A—C5—H5B109.5O112—S1—C10093.3 (9)
N2—C5—H5C109.5F12—C100—F13109.3 (3)
H5A—C5—H5C109.5F12—C100—F11107.6 (3)
H5B—C5—H5C109.5F13—C100—F11104.1 (2)
N2—C6—H6A109.5F12—C100—S1113.09 (19)
N2—C6—H6B109.5F13—C100—S1112.99 (19)
H6A—C6—H6B109.5F11—C100—S1109.3 (2)
N2—C6—H6C109.5O21—S2—O23115.31 (12)
H6A—C6—H6C109.5O21—S2—O22114.63 (12)
H6B—C6—H6C109.5O23—S2—O22115.08 (12)
N3—C7—H7A109.5O21—S2—C200103.63 (12)
N3—C7—H7B109.5O23—S2—C200103.20 (11)
H7A—C7—H7B109.5O22—S2—C200102.54 (11)
N3—C7—H7C109.5F23—C200—F21107.6 (2)
H7A—C7—H7C109.5F23—C200—F22106.7 (2)
H7B—C7—H7C109.5F21—C200—F22107.4 (2)
N3—C8—H8A109.5F23—C200—S2111.78 (16)
N3—C8—H8B109.5F21—C200—S2112.38 (17)
H8A—C8—H8B109.5F22—C200—S2110.72 (17)
C9—N4—C1—C2130.8 (2)O111—S1—C100—F1260.9 (3)
N4—C1—C2—C3169.80 (17)O121—S1—C100—F12178.1 (2)
C4—N1—C3—C2140.4 (2)O131—S1—C100—F1257.8 (3)
C1—C2—C3—N1177.71 (17)O112—S1—C100—F12103.6 (8)
C3—N1—C4—N330.0 (3)O132—S1—C100—F13142.2 (9)
C3—N1—C4—N2149.9 (2)O122—S1—C100—F1394.4 (8)
C8—N3—C4—N130.8 (3)O111—S1—C100—F1363.9 (3)
C7—N3—C4—N1147.6 (2)O121—S1—C100—F1357.1 (3)
C8—N3—C4—N2149.3 (2)O131—S1—C100—F13177.3 (2)
C7—N3—C4—N232.3 (3)O112—S1—C100—F1321.2 (8)
C6—N2—C4—N125.1 (3)O132—S1—C100—F11102.4 (9)
C5—N2—C4—N1145.5 (2)O122—S1—C100—F1120.9 (8)
C6—N2—C4—N3154.8 (2)O111—S1—C100—F11179.3 (2)
C5—N2—C4—N334.6 (3)O121—S1—C100—F1158.3 (2)
C1—N4—C9—N6147.78 (19)O131—S1—C100—F1162.0 (2)
C1—N4—C9—N533.7 (3)O112—S1—C100—F11136.5 (8)
C12—N6—C9—N4149.6 (2)O21—S2—C200—F23176.20 (17)
C13—N6—C9—N422.5 (3)O23—S2—C200—F2355.63 (19)
C12—N6—C9—N528.9 (3)O22—S2—C200—F2364.25 (19)
C13—N6—C9—N5159.0 (2)O21—S2—C200—F2162.7 (2)
C10—N5—C9—N4142.8 (2)O23—S2—C200—F21176.76 (18)
C11—N5—C9—N436.3 (3)O22—S2—C200—F2156.9 (2)
C10—N5—C9—N638.7 (3)O21—S2—C200—F2257.38 (19)
C11—N5—C9—N6142.1 (2)O23—S2—C200—F2263.20 (19)
O132—S1—C100—F1217.4 (9)O22—S2—C200—F22176.93 (17)
O122—S1—C100—F12140.8 (8)

Experimental details

(I)(II)(III)(IV)
Crystal data
Chemical formulaC13H32N62+·2BrC13H32N62+·BC24H20·Cl(C13H32N6)[HgCl4]C13H32N62+·2CF3O3S
Mr432.27627.11614.84570.59
Crystal system, space groupTriclinic, P1Monoclinic, P21/cMonoclinic, P21/cTriclinic, P1
Temperature (K)120150120120
a, b, c (Å)12.4256 (14), 12.5254 (15), 12.6935 (15)17.5770 (8), 9.3797 (4), 22.4953 (10)8.3199 (4), 18.0809 (9), 15.8086 (8)8.8771 (7), 12.3802 (10), 12.5704 (10)
α, β, γ (°)79.465 (3), 89.731 (3), 89.361 (2)90, 107.034 (1), 9090, 104.291 (1), 90108.939 (2), 91.478 (2), 97.775 (2)
V3)1942.1 (4)3546.0 (3)2304.5 (2)1291.10 (18)
Z4442
Radiation typeMo KαMo KαMo KαMo Kα
µ (mm1)4.180.147.150.29
Crystal size (mm)0.42 × 0.22 × 0.200.20 × 0.20 × 0.150.45 × 0.20 × 0.080.40 × 0.20 × 0.20
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Bruker SMART CCD area-detector
diffractometer
Bruker SMART CCD area-detector
diffractometer
Bruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2002)
Multi-scan
(SADABS; Bruker, 2002)
Multi-scan
(SADABS; Bruker, 2002)
Multi-scan
(SADABS; Bruker, 2002)
Tmin, Tmax0.243, 0.4350.962, 0.9750.133, 0.5630.893, 0.944
No. of measured, independent and
observed [I > 2σ(I)] reflections
19556, 9242, 5769 39279, 7800, 4307 23407, 5049, 4421 7636, 5165, 4404
Rint0.0650.1000.0250.012
(sin θ/λ)max1)0.6580.6410.6410.625
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.058, 0.139, 0.99 0.044, 0.072, 0.91 0.028, 0.087, 1.07 0.046, 0.121, 1.03
No. of reflections9242780050495165
No. of parameters387414225337
No. of restraints00030
H-atom treatmentH-atom parameters constrainedH-atom parameters constrainedH-atom parameters constrainedH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.95, 0.890.21, 0.240.92, 0.550.76, 0.51

Computer programs: SMART (Bruker, 2002), SMART, SAINT (Bruker, 2002), SAINT (Bruker, 2002, SHELXTL (Bruker, 2002), SHELXTL (Bruker, 2002, SHELXTL.

Selected torsion angles (°) for compounds (I)-(V) top
Torsion angle(I)(II)(III)(IV)(V)
N4—C1—C2—C3-62.8 (6)63.4 (2)-179.9 (3)-169.8 (2)69.8 (2)
C1—C2—C3—N1-173.4 (4)-177.6 (2)175.5 (3)177.7 (2)-173.3 (1)
Hydrogen bond parameters (Å, °) for compounds (I)-(IV) top
CompoundD—H···AD—HH···AD···AD—H···A
(Ia)N11—H11···Br10.882.423.282 (4)168
(Ib)N21—H21···Br40.882.433.283 (4)165
(Ib)N24—H24···Br20.882.543.396 (4)166
(Ia)N14—H14···Br30.882.523.373 (4)165
(Ib)C28—H20Q···Br4i0.982.813.736 (6)158
(Ib)C213—H21M···Br2ii0.982.823.764 (5)163
(II)N1—H1···Cl1iii0.882.413.2516 (18)160
(II)N4—H4···Cl10.882.293.1668 (17)172
(III)N1—H1···Cl40.882.503.349 (4)164
(III)N4—H4···Cl10.882.363.215 (4)164
(III)C1—H1A···Cl3iv0.992.653.597 (4)161
(IV)N4—H4···O220.882.032.796 (2)144
(IV)N1—H1···O1110.881.982.855 (3)172
(IV)N1—H1···O1120.882.052.883 (18)157
(IV)C2—H2B···O1120.992.443.171 (19)130
(IV)C5—H5C···O21v0.982.493.448 (3)166
(IV)C7—H7B···O132vi0.982.253.111 (17)145
(IV)C8—H8A···O131vi0.982.463.245 (3)137
Symmetry codes: i (-x + 2,-y + 1,-z + 1); ii (-x + 1,-y + 2,-z + 1); iii (-x + 1,-y,-z + 1); iv (x − 1,y,z); v (x,y,z + 1); vi (x − 1,y,z);
 

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