Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680702418X/bt2370sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680702418X/bt2370Isup2.hkl |
CCDC reference: 650711
Key indicators
- Single-crystal X-ray study
- T = 291 K
- Mean (C-C) = 0.005 Å
- R factor = 0.023
- wR factor = 0.057
- Data-to-parameter ratio = 17.0
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for C6 - C7 .. 6.50 su PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Fe1
Alert level G PLAT794_ALERT_5_G Check Predicted Bond Valency for Fe1 (2) 2.81
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
For details of other tetrahalogenoferrates with quinoline and its derivatives, see: Bottomley et al. (1984), Warnke et al. (2006), Wyrzykowski, Sikorski, Konitz et al. (2006), Wyrzykowski, Sikorski, Lis et al. (2006), Wyrzykowski, Warnke et al. (2006); and for similar tetrahalogenoferrates with aromatic amines acting as balancing cations see: Abboud et al. (2005), Barbaro et al. (1992), Chan & Baird (2004), Couce et al. (1995), Daran et al. (1979), James et al. (2001), James et al. (1982), Khan et al. (1987), Lowe et al. (1990), Lowe et al. (1994), Hackert & Jacobson (1971), Podesta & Orpen (2005), Shaviv et al. (1992), Veidis et al. (1979), Veidis et al. (1981), Zora et al. (1990), Zordan et al. (2005). For general synthesis procedures see: Warnke et al. (2003).
For related literature, see: Desiraju & Steiner (1999).
For related literature, see: Hackert & Jacobson (1971).
To a solution of FeBr3 (ca 0.025 mol) in ethanol (96%) (50 ml), a stoichiometric quantity of a 40% HBr solution and 8-methylquinoline (ca 0.025 mol) were added in turn. The compound crystallized directly from the reaction mixture at ambient temperature. After ca 3 months dark-red crystals appeared. The compound was dried over P4O10 in a vacuum desiccator. Elemental analysis (calculated/found %): C 32.38/32.28, H 2.69/2.66, N 3.77/3.80, Br 53.74/53.54, Fe 7.51/7.28.
The carbon-bonded hydrogen atoms were placed in calculated positions and were refined as riding on adjacent carbon atom with fixed U values [Uiso(H) = 1.2Ueq(C) or Uiso(H) = 1.5Ueq(C-methyl)]. The methyl groups were allowed to rotate about their local threefold axis (AFIX 137). The nitrogen-bonded hydrogen atoms were founded from difference Fourier synthesis after eight cycles of anisotropic refinement and were refined as riding on adjacent nitrogen atom with fixed U values (Uiso(H) = 1.2Ueq(N).
The composition of quinolinium and methylquinolinium tetrahalogenoferrates(III) has been found to be distinctly dependent on location of the methyl substituent in the quinoline ring and the kind of halide ligands in the coordination sphere of Fe(III) (Warnke et al., 2003). When a quinolinum cation is a counter-ion, both the [FeBr4]- and [FeCl4]- anions form binary (1:1) salts (Wyrzykowski, Sikorski, Konitz et al., 2006). With a 2-methyl substituted quinolinium cation, resulting salts have a composition of (2MeQH)2[FeX4]X (where 2MeQH is 2-methylquinolinum cation, and X = Br or Cl) (Warnke et al., 2006; Wyrzykowski, Sikorski, Lis et al., 2006). Introduction of the 2-methylquinoline substituted at position 4 by —NH2 leads again to formation of 1:1 salt (Wyrzykowski, Warnke et al., 2006). Thus determining the composition of FeBr4 complex containing quinoline methylated at another position was interesting, and in future can lead to general conclusions about influence of quinoline substituents on complex composition.
All 8-methylquinolinium cations intramolecular distances and angles in (I) (Fig. 1) can be considered normal. All atoms lie in general positions. The asymmetric unit contains two protonated 8-methylquinolinium cations, one bromide anion and one tetrabromoferrate anion. The mean Fe—Br distance is 2.3338 (6) Å. Two Br—Fe—Br angles are smaller than tetrahedral, two are almost tetrahedral, and two are greater than tetrahedral. The 8-methylquinolinium cations can be considered planar and are inclined at 5.25 (9)°. From weighted least-squares planes calculated through all non-hydrogen atoms of the cations the most deviating atoms are C7 [0.025 (3) Å] in one molecule and C14 [0.026 (3) Å] in the second molecule. The two 8-methylquinolinium cations and bromide anion are connected via N—H···Br hydrogen bonds (Table 1, Fig. 2). In the structure can be found one more intermolecular C—H···Br short contact (Table 2), which, according to Desiraju & Steiner (1999), can be considered as a weak hydrogen bond. The cations are associated via π···π stacking interactions (Table 2) to dimers, and dimers are separated by anions one form each other. Thus, in considered structure, tetrabromoferrate anions play role of stacking breaker. The N—H···Br hydrogen bonds link the molecules to a chain running along [2 1 0] (Fig. 2).
For details of other tetrahalogenoferrates with quinoline and its derivatives, see: Bottomley et al. (1984), Warnke et al. (2006), Wyrzykowski, Sikorski, Konitz et al. (2006), Wyrzykowski, Sikorski, Lis et al. (2006), Wyrzykowski, Warnke et al. (2006); and for similar tetrahalogenoferrates with aromatic amines acting as balancing cations see: Abboud et al. (2005), Barbaro et al. (1992), Chan & Baird (2004), Couce et al. (1995), Daran et al. (1979), James et al. (2001), James et al. (1982), Khan et al. (1987), Lowe et al. (1990), Lowe et al. (1994), Hackert & Jacobson (1971), Podesta & Orpen (2005), Shaviv et al. (1992), Veidis et al. (1979), Veidis et al. (1981), Zora et al. (1990), Zordan et al. (2005). For general synthesis procedures see: Warnke et al. (2003).
For related literature, see: Desiraju & Steiner (1999).
For related literature, see: Hackert & Jacobson (1971).
Data collection: CrysAlis CCD v. 1.163 (UNIL IC & KUMA 2000); cell refinement: CrysAlis RED v. 1.163 (UNIL IC & KUMA 2000); data reduction: CrysAlis RED v. 1.163; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL/PC (Sheldrick, 1990b) ORTEP-3 W v. 1.062 (Farrugia 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997) and PLATON (Spek, 1990).
(C10H10N)2[FeBr4]Br | Z = 2 |
Mr = 743.78 | F(000) = 710 |
Triclinic, P1 | Dx = 2.007 Mg m−3 Dm = 2.01 Mg m−3 Dm measured by Berman density torsion balance |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.9533 (5) Å | Cell parameters from 7884 reflections |
b = 10.3853 (4) Å | θ = 5–20° |
c = 15.2432 (8) Å | µ = 8.74 mm−1 |
α = 84.781 (4)° | T = 291 K |
β = 79.645 (5)° | Plate, orange |
γ = 85.556 (4)° | 0.38 × 0.11 × 0.03 mm |
V = 1231.00 (11) Å3 |
Kuma KM4-CCD diffractometer | 4345 independent reflections |
Radiation source: fine-focus sealed tube | 3120 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.020 |
Detector resolution: 1048576 pixels mm-1 | θmax = 25.1°, θmin = 2.0° |
ω scans | h = −8→9 |
Absorption correction: numerical X-RED. STOE & Cie (1999) | k = −12→12 |
Tmin = 0.321, Tmax = 0.780 | l = −16→18 |
12314 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.023 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.057 | H-atom parameters constrained |
S = 0.98 | w = 1/[σ2(Fo2) + (0.0304P)2] where P = (Fo2 + 2Fc2)/3 |
4345 reflections | (Δ/σ)max = 0.001 |
255 parameters | Δρmax = 0.43 e Å−3 |
0 restraints | Δρmin = −0.57 e Å−3 |
(C10H10N)2[FeBr4]Br | γ = 85.556 (4)° |
Mr = 743.78 | V = 1231.00 (11) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.9533 (5) Å | Mo Kα radiation |
b = 10.3853 (4) Å | µ = 8.74 mm−1 |
c = 15.2432 (8) Å | T = 291 K |
α = 84.781 (4)° | 0.38 × 0.11 × 0.03 mm |
β = 79.645 (5)° |
Kuma KM4-CCD diffractometer | 4345 independent reflections |
Absorption correction: numerical X-RED. STOE & Cie (1999) | 3120 reflections with I > 2σ(I) |
Tmin = 0.321, Tmax = 0.780 | Rint = 0.020 |
12314 measured reflections |
R[F2 > 2σ(F2)] = 0.023 | 0 restraints |
wR(F2) = 0.057 | H-atom parameters constrained |
S = 0.98 | Δρmax = 0.43 e Å−3 |
4345 reflections | Δρmin = −0.57 e Å−3 |
255 parameters |
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 > 2σ(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. |
x | y | z | Uiso*/Ueq | ||
Fe1 | 0.84814 (6) | 0.24354 (4) | 0.12389 (3) | 0.04493 (13) | |
Br1 | 0.82953 (4) | 0.02568 (3) | 0.10380 (2) | 0.05566 (11) | |
Br2 | 1.10108 (4) | 0.31300 (3) | 0.03423 (2) | 0.05990 (11) | |
Br4 | 0.61015 (5) | 0.36204 (4) | 0.08073 (3) | 0.06862 (13) | |
Br5 | 0.86151 (6) | 0.26018 (5) | 0.27339 (3) | 0.08107 (14) | |
N1 | 0.4142 (3) | 1.0191 (2) | 0.24958 (17) | 0.0491 (7) | |
H1N | 0.4300 | 1.0708 | 0.2958 | 0.059* | |
C1 | 0.3428 (4) | 1.0733 (3) | 0.1817 (2) | 0.0580 (9) | |
H1 | 0.2962 | 1.1582 | 0.1832 | 0.070* | |
C2 | 0.3373 (4) | 1.0048 (4) | 0.1094 (2) | 0.0654 (10) | |
H2 | 0.2877 | 1.0430 | 0.0617 | 0.078* | |
C3 | 0.4047 (4) | 0.8812 (4) | 0.1083 (2) | 0.0610 (10) | |
H3 | 0.4010 | 0.8348 | 0.0594 | 0.073* | |
C4 | 0.4800 (4) | 0.8217 (3) | 0.1789 (2) | 0.0498 (8) | |
C5 | 0.4844 (4) | 0.8946 (3) | 0.2527 (2) | 0.0461 (8) | |
C6 | 0.5485 (4) | 0.6941 (4) | 0.1818 (3) | 0.0634 (10) | |
H6 | 0.5488 | 0.6445 | 0.1340 | 0.076* | |
C7 | 0.6143 (5) | 0.6420 (4) | 0.2538 (3) | 0.0780 (13) | |
H7 | 0.6563 | 0.5559 | 0.2557 | 0.094* | |
C8 | 0.6205 (4) | 0.7161 (4) | 0.3261 (3) | 0.0680 (11) | |
H8 | 0.6685 | 0.6782 | 0.3743 | 0.082* | |
C9 | 0.5574 (4) | 0.8425 (3) | 0.3269 (2) | 0.0543 (9) | |
C10 | 0.5637 (5) | 0.9234 (4) | 0.4024 (2) | 0.0799 (12) | |
H10A | 0.6154 | 0.8724 | 0.4474 | 0.120* | |
H10B | 0.4495 | 0.9531 | 0.4277 | 0.120* | |
H10C | 0.6301 | 0.9966 | 0.3804 | 0.120* | |
N11 | 0.1901 (3) | 0.5284 (2) | 0.31091 (18) | 0.0494 (7) | |
H11N | 0.2398 | 0.4574 | 0.3473 | 0.059* | |
C11 | 0.1751 (4) | 0.5010 (3) | 0.2300 (2) | 0.0581 (9) | |
H11 | 0.2104 | 0.4188 | 0.2116 | 0.070* | |
C12 | 0.1075 (5) | 0.5929 (3) | 0.1723 (3) | 0.0648 (10) | |
H12 | 0.0967 | 0.5732 | 0.1153 | 0.078* | |
C13 | 0.0573 (4) | 0.7127 (3) | 0.2003 (2) | 0.0603 (9) | |
H13 | 0.0107 | 0.7750 | 0.1622 | 0.072* | |
C14 | 0.0747 (4) | 0.7440 (3) | 0.2859 (2) | 0.0502 (8) | |
C15 | 0.1451 (4) | 0.6474 (3) | 0.3433 (2) | 0.0456 (8) | |
C16 | 0.0312 (5) | 0.8670 (4) | 0.3157 (3) | 0.0669 (10) | |
H16 | −0.0146 | 0.9320 | 0.2792 | 0.080* | |
C17 | 0.0557 (5) | 0.8919 (4) | 0.3977 (3) | 0.0823 (12) | |
H17 | 0.0274 | 0.9744 | 0.4172 | 0.099* | |
C18 | 0.1232 (5) | 0.7949 (4) | 0.4539 (3) | 0.0826 (13) | |
H18 | 0.1367 | 0.8146 | 0.5105 | 0.099* | |
C19 | 0.1701 (4) | 0.6718 (3) | 0.4288 (2) | 0.0624 (10) | |
C20 | 0.2449 (5) | 0.5689 (4) | 0.4901 (2) | 0.0845 (13) | |
H20A | 0.2644 | 0.6069 | 0.5422 | 0.127* | |
H20B | 0.3514 | 0.5326 | 0.4591 | 0.127* | |
H20C | 0.1663 | 0.5018 | 0.5078 | 0.127* | |
Br99 | 0.31991 (6) | 0.24911 (4) | 0.38250 (3) | 0.08361 (16) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Fe1 | 0.0569 (3) | 0.0382 (3) | 0.0423 (3) | 0.0022 (2) | −0.0162 (2) | −0.0065 (2) |
Br1 | 0.0671 (2) | 0.03822 (19) | 0.0643 (2) | −0.00061 (16) | −0.01844 (18) | −0.00616 (16) |
Br2 | 0.0676 (2) | 0.0539 (2) | 0.0579 (2) | −0.00829 (17) | −0.01148 (18) | 0.00184 (17) |
Br4 | 0.0731 (3) | 0.0532 (2) | 0.0841 (3) | 0.01958 (18) | −0.0308 (2) | −0.0154 (2) |
Br5 | 0.1119 (3) | 0.0926 (3) | 0.0433 (2) | −0.0105 (3) | −0.0195 (2) | −0.0148 (2) |
N1 | 0.0650 (17) | 0.0445 (16) | 0.0415 (16) | 0.0087 (13) | −0.0197 (14) | −0.0121 (13) |
C1 | 0.068 (2) | 0.049 (2) | 0.058 (2) | 0.0062 (17) | −0.0183 (19) | −0.0016 (18) |
C2 | 0.075 (3) | 0.076 (3) | 0.050 (2) | −0.005 (2) | −0.0211 (19) | −0.009 (2) |
C3 | 0.068 (2) | 0.076 (3) | 0.044 (2) | −0.012 (2) | −0.0102 (18) | −0.0240 (19) |
C4 | 0.049 (2) | 0.050 (2) | 0.050 (2) | −0.0086 (16) | −0.0003 (16) | −0.0152 (17) |
C5 | 0.052 (2) | 0.0398 (19) | 0.046 (2) | 0.0022 (15) | −0.0082 (16) | −0.0071 (15) |
C6 | 0.059 (2) | 0.048 (2) | 0.081 (3) | −0.0017 (18) | 0.002 (2) | −0.022 (2) |
C7 | 0.070 (3) | 0.036 (2) | 0.120 (4) | 0.0106 (18) | 0.004 (3) | −0.014 (2) |
C8 | 0.066 (2) | 0.056 (2) | 0.076 (3) | 0.0125 (19) | −0.009 (2) | 0.005 (2) |
C9 | 0.060 (2) | 0.048 (2) | 0.053 (2) | 0.0083 (17) | −0.0103 (18) | −0.0062 (17) |
C10 | 0.103 (3) | 0.088 (3) | 0.055 (3) | 0.018 (2) | −0.038 (2) | −0.009 (2) |
N11 | 0.0596 (17) | 0.0384 (15) | 0.0500 (18) | 0.0000 (13) | −0.0139 (14) | 0.0033 (13) |
C11 | 0.081 (3) | 0.042 (2) | 0.058 (2) | −0.0044 (17) | −0.026 (2) | −0.0095 (17) |
C12 | 0.095 (3) | 0.052 (2) | 0.056 (2) | −0.009 (2) | −0.036 (2) | 0.0004 (18) |
C13 | 0.071 (2) | 0.048 (2) | 0.065 (3) | 0.0004 (18) | −0.029 (2) | 0.0077 (18) |
C14 | 0.052 (2) | 0.045 (2) | 0.053 (2) | 0.0009 (16) | −0.0101 (17) | −0.0005 (16) |
C15 | 0.0498 (19) | 0.0401 (19) | 0.045 (2) | 0.0051 (15) | −0.0052 (15) | −0.0038 (15) |
C16 | 0.079 (3) | 0.053 (2) | 0.062 (3) | 0.0169 (19) | −0.004 (2) | −0.0021 (19) |
C17 | 0.110 (3) | 0.058 (3) | 0.072 (3) | 0.022 (2) | 0.000 (2) | −0.020 (2) |
C18 | 0.120 (3) | 0.074 (3) | 0.049 (2) | 0.023 (3) | −0.007 (2) | −0.021 (2) |
C19 | 0.078 (3) | 0.056 (2) | 0.049 (2) | 0.0091 (19) | −0.0057 (19) | −0.0054 (18) |
C20 | 0.128 (4) | 0.077 (3) | 0.052 (2) | 0.016 (3) | −0.032 (2) | −0.006 (2) |
Br99 | 0.1428 (4) | 0.0520 (2) | 0.0567 (3) | 0.0362 (2) | −0.0337 (3) | −0.01146 (19) |
Fe1—Br5 | 2.3230 (6) | C10—H10B | 0.9600 |
Fe1—Br1 | 2.3300 (5) | C10—H10C | 0.9600 |
Fe1—Br4 | 2.3387 (5) | N11—C11 | 1.318 (4) |
Fe1—Br2 | 2.3436 (6) | N11—C15 | 1.370 (4) |
N1—C1 | 1.329 (4) | N11—H11N | 0.9828 |
N1—C5 | 1.368 (4) | C11—C12 | 1.383 (4) |
N1—H1N | 0.9551 | C11—H11 | 0.9300 |
C1—C2 | 1.374 (4) | C12—C13 | 1.359 (5) |
C1—H1 | 0.9300 | C12—H12 | 0.9300 |
C2—C3 | 1.353 (5) | C13—C14 | 1.405 (5) |
C2—H2 | 0.9300 | C13—H13 | 0.9300 |
C3—C4 | 1.398 (5) | C14—C16 | 1.393 (4) |
C3—H3 | 0.9300 | C14—C15 | 1.420 (4) |
C4—C6 | 1.393 (5) | C15—C19 | 1.401 (4) |
C4—C5 | 1.418 (4) | C16—C17 | 1.350 (5) |
C5—C9 | 1.410 (4) | C16—H16 | 0.9300 |
C6—C7 | 1.351 (5) | C17—C18 | 1.401 (5) |
C6—H6 | 0.9300 | C17—H17 | 0.9300 |
C7—C8 | 1.409 (5) | C18—C19 | 1.373 (5) |
C7—H7 | 0.9300 | C18—H18 | 0.9300 |
C8—C9 | 1.369 (5) | C19—C20 | 1.512 (5) |
C8—H8 | 0.9300 | C20—H20A | 0.9600 |
C9—C10 | 1.494 (5) | C20—H20B | 0.9600 |
C10—H10A | 0.9600 | C20—H20C | 0.9600 |
Br5—Fe1—Br1 | 107.92 (2) | C9—C10—H10C | 109.5 |
Br5—Fe1—Br4 | 112.12 (2) | H10A—C10—H10C | 109.5 |
Br1—Fe1—Br4 | 108.87 (2) | H10B—C10—H10C | 109.5 |
Br5—Fe1—Br2 | 109.50 (2) | C11—N11—C15 | 123.8 (3) |
Br1—Fe1—Br2 | 107.98 (2) | C11—N11—H11N | 115.3 |
Br4—Fe1—Br2 | 110.33 (2) | C15—N11—H11N | 120.9 |
C1—N1—C5 | 123.2 (3) | N11—C11—C12 | 120.8 (3) |
C1—N1—H1N | 119.6 | N11—C11—H11 | 119.6 |
C5—N1—H1N | 116.8 | C12—C11—H11 | 119.6 |
N1—C1—C2 | 120.5 (3) | C13—C12—C11 | 118.7 (3) |
N1—C1—H1 | 119.8 | C13—C12—H12 | 120.6 |
C2—C1—H1 | 119.8 | C11—C12—H12 | 120.6 |
C3—C2—C1 | 119.2 (3) | C12—C13—C14 | 121.1 (3) |
C3—C2—H2 | 120.4 | C12—C13—H13 | 119.5 |
C1—C2—H2 | 120.4 | C14—C13—H13 | 119.5 |
C2—C3—C4 | 121.5 (3) | C16—C14—C13 | 122.8 (3) |
C2—C3—H3 | 119.2 | C16—C14—C15 | 118.5 (3) |
C4—C3—H3 | 119.2 | C13—C14—C15 | 118.7 (3) |
C6—C4—C3 | 123.8 (3) | N11—C15—C19 | 121.0 (3) |
C6—C4—C5 | 118.0 (3) | N11—C15—C14 | 116.8 (3) |
C3—C4—C5 | 118.2 (3) | C19—C15—C14 | 122.1 (3) |
N1—C5—C9 | 120.5 (3) | C17—C16—C14 | 119.9 (4) |
N1—C5—C4 | 117.4 (3) | C17—C16—H16 | 120.0 |
C9—C5—C4 | 122.1 (3) | C14—C16—H16 | 120.0 |
C7—C6—C4 | 120.3 (3) | C16—C17—C18 | 120.8 (4) |
C7—C6—H6 | 119.8 | C16—C17—H17 | 119.6 |
C4—C6—H6 | 119.8 | C18—C17—H17 | 119.6 |
C6—C7—C8 | 121.1 (3) | C19—C18—C17 | 122.5 (4) |
C6—C7—H7 | 119.4 | C19—C18—H18 | 118.7 |
C8—C7—H7 | 119.4 | C17—C18—H18 | 118.7 |
C9—C8—C7 | 121.4 (4) | C18—C19—C15 | 116.2 (3) |
C9—C8—H8 | 119.3 | C18—C19—C20 | 121.7 (4) |
C7—C8—H8 | 119.3 | C15—C19—C20 | 122.1 (3) |
C8—C9—C5 | 116.9 (3) | C19—C20—H20A | 109.5 |
C8—C9—C10 | 122.5 (3) | C19—C20—H20B | 109.5 |
C5—C9—C10 | 120.6 (3) | H20A—C20—H20B | 109.5 |
C9—C10—H10A | 109.5 | C19—C20—H20C | 109.5 |
C9—C10—H10B | 109.5 | H20A—C20—H20C | 109.5 |
H10A—C10—H10B | 109.5 | H20B—C20—H20C | 109.5 |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···Br99i | 0.96 | 2.39 | 3.229 (2) | 146 |
N11—H11N···Br99 | 0.98 | 2.25 | 3.168 (3) | 155 |
C10—H10A···Br99ii | 0.96 | 2.89 | 3.819 (4) | 163 |
Symmetry codes: (i) x, y+1, z; (ii) −x+1, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | (C10H10N)2[FeBr4]Br |
Mr | 743.78 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 291 |
a, b, c (Å) | 7.9533 (5), 10.3853 (4), 15.2432 (8) |
α, β, γ (°) | 84.781 (4), 79.645 (5), 85.556 (4) |
V (Å3) | 1231.00 (11) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 8.74 |
Crystal size (mm) | 0.38 × 0.11 × 0.03 |
Data collection | |
Diffractometer | Kuma KM4-CCD |
Absorption correction | Numerical X-RED. STOE & Cie (1999) |
Tmin, Tmax | 0.321, 0.780 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12314, 4345, 3120 |
Rint | 0.020 |
(sin θ/λ)max (Å−1) | 0.596 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.023, 0.057, 0.98 |
No. of reflections | 4345 |
No. of parameters | 255 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.43, −0.57 |
Computer programs: CrysAlis CCD v. 1.163 (UNIL IC & KUMA 2000), CrysAlis RED v. 1.163 (UNIL IC & KUMA 2000), CrysAlis RED v. 1.163, SHELXS97 (Sheldrick, 1990a), XP in SHELXTL/PC (Sheldrick, 1990b) ORTEP-3 W v. 1.062 (Farrugia 1997), SHELXL97 (Sheldrick, 1997) and PLATON (Spek, 1990).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···Br99i | 0.96 | 2.39 | 3.229 (2) | 146.2 |
N11—H11N···Br99 | 0.98 | 2.25 | 3.168 (3) | 154.5 |
C10—H10A···Br99ii | 0.96 | 2.89 | 3.819 (4) | 162.6 |
Symmetry codes: (i) x, y+1, z; (ii) −x+1, −y+1, −z+1. |
Cg(I)···Cg(J) | Cg···Cg | α | β | γ | Cg(I)p | Cg(J)p |
Cg(N1)···Cg(C19) | 3.8970 | 5.16 | 25.25 | 30.36 | 3.363 | 3.525 |
Cg(C9)···Cg(N11) | 3.8130 | 5.14 | 26.19 | 21.42 | 3.550 | 3.421 |
Cg(C9)···Cg(C19) | 3.7089 | 4.14 | 17.96 | 17.24 | 3.542 | 3.528 |
Cg···Cg - distance between ring centroids, α - dihedral Angle between Planes I and J, β - angle between Cg(I)-->Cg(J) vector and normal to plane I, γ - angle between Cg(I)-->Cg(J) vector and normal to plane J, Cg(I)p perpendicular distance of Cg(I) on ring J, Cg(J)p perpendicular distance of Cg(J) on ring I. |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- If you have already subscribed, you may need to register
The composition of quinolinium and methylquinolinium tetrahalogenoferrates(III) has been found to be distinctly dependent on location of the methyl substituent in the quinoline ring and the kind of halide ligands in the coordination sphere of Fe(III) (Warnke et al., 2003). When a quinolinum cation is a counter-ion, both the [FeBr4]- and [FeCl4]- anions form binary (1:1) salts (Wyrzykowski, Sikorski, Konitz et al., 2006). With a 2-methyl substituted quinolinium cation, resulting salts have a composition of (2MeQH)2[FeX4]X (where 2MeQH is 2-methylquinolinum cation, and X = Br or Cl) (Warnke et al., 2006; Wyrzykowski, Sikorski, Lis et al., 2006). Introduction of the 2-methylquinoline substituted at position 4 by —NH2 leads again to formation of 1:1 salt (Wyrzykowski, Warnke et al., 2006). Thus determining the composition of FeBr4 complex containing quinoline methylated at another position was interesting, and in future can lead to general conclusions about influence of quinoline substituents on complex composition.
All 8-methylquinolinium cations intramolecular distances and angles in (I) (Fig. 1) can be considered normal. All atoms lie in general positions. The asymmetric unit contains two protonated 8-methylquinolinium cations, one bromide anion and one tetrabromoferrate anion. The mean Fe—Br distance is 2.3338 (6) Å. Two Br—Fe—Br angles are smaller than tetrahedral, two are almost tetrahedral, and two are greater than tetrahedral. The 8-methylquinolinium cations can be considered planar and are inclined at 5.25 (9)°. From weighted least-squares planes calculated through all non-hydrogen atoms of the cations the most deviating atoms are C7 [0.025 (3) Å] in one molecule and C14 [0.026 (3) Å] in the second molecule. The two 8-methylquinolinium cations and bromide anion are connected via N—H···Br hydrogen bonds (Table 1, Fig. 2). In the structure can be found one more intermolecular C—H···Br short contact (Table 2), which, according to Desiraju & Steiner (1999), can be considered as a weak hydrogen bond. The cations are associated via π···π stacking interactions (Table 2) to dimers, and dimers are separated by anions one form each other. Thus, in considered structure, tetrabromoferrate anions play role of stacking breaker. The N—H···Br hydrogen bonds link the molecules to a chain running along [2 1 0] (Fig. 2).