Bis(2-methyl­quinolinium) tetra­chloro­ferrate(III) chloride

The asymmetric unit of the title compound, (C₁₀H₁₀N)₂[FeCl₄]Cl, consists of two 2-methyl­quinolinium cations, a tetra­chloro­ferrate(III) anion with one of the Cl atoms disordered, and a chloride anion. In the crystal structure, there are π–π stacking interactions between the cations in an ABBA arrangement, N—H...Cl hydrogen bonds, and Fe—Cl...π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• Disorder in main residue
• R factor = 0.026
• wR factor = 0.067
• Data-to-parameter ratio = 20.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT301_ALERT_3_C Main Residue  Disorder .........................       3.00 Perc.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2003); cell refinement: CrysAlis RED (Oxford Diffraction, 2003); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: Mercury (Bruno et al., 2002); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).

Bis(2-methylquinolinium) tetrachloroferrate(III) chloride

Crystal data

(C10H10N)2[FeCl4]Cl	Z = 2
Mr = 521.48	F(000) = 530
Triclinic, P1	Dx = 1.521 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.645 (2) Å	Cell parameters from 15685 reflections
b = 10.888 (3) Å	θ = 3.5–27.8°
c = 13.503 (3) Å	µ = 1.26 mm^−1
α = 112.98 (3)°	T = 100 K
β = 100.46 (3)°	Prism, green
γ = 93.32 (3)°	0.5 × 0.4 × 0.4 mm
V = 1139.0 (6) Å^3

Data collection

Kuma KM-4-CCD κ-geometry diffractometer	5318 independent reflections
Radiation source: fine-focus sealed tube	4884 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
ω scans	θmax = 27.8°, θmin = 3.5°
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2003)	h = −11→11
Tmin = 0.516, Tmax = 0.659	k = −14→13
15108 measured reflections	l = −17→17

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.026	H-atom parameters constrained
wR(F^2) = 0.067	w = 1/[σ^2(Fo^2) + (0.0324P)^2 + 0.6399P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max = 0.002
5318 reflections	Δρmax = 0.37 e Å^−3
261 parameters	Δρmin = −0.42 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0070 (7)

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Fe1	0.86331 (2)	0.16692 (2)	0.351496 (17)	0.01666 (7)
Cl1	0.80913 (5)	0.37152 (4)	0.37881 (3)	0.02519 (9)
Cl2	0.88722 (5)	0.05993 (4)	0.18000 (3)	0.02890 (10)
Cl3	1.09034 (17)	0.1826 (3)	0.46175 (7)	0.0270 (4)	0.931 (12)
Cl31	1.067 (2)	0.1425 (19)	0.4562 (8)	0.024 (2)*	0.069 (12)
Cl4	0.67323 (5)	0.06072 (4)	0.38653 (4)	0.03320 (11)
Cl5	0.55145 (4)	0.26335 (4)	0.95713 (3)	0.02138 (9)
N1	0.53352 (14)	0.67298 (12)	0.81939 (10)	0.0173 (2)
H1A	0.4934	0.6963	0.8785	0.021*
C2	0.61075 (18)	0.76890 (15)	0.80288 (12)	0.0197 (3)
C3	0.67627 (19)	0.73207 (16)	0.70843 (13)	0.0227 (3)
H3A	0.7309	0.7999	0.6946	0.027*
C4	0.66207 (18)	0.60060 (16)	0.63697 (12)	0.0209 (3)
H4A	0.7086	0.5770	0.5746	0.025*
C5	0.55764 (18)	0.36123 (16)	0.58427 (12)	0.0205 (3)
H5A	0.6020	0.3320	0.5208	0.025*
C6	0.47347 (18)	0.27020 (16)	0.60755 (13)	0.0224 (3)
H6A	0.4575	0.1774	0.5592	0.027*
C7	0.40964 (18)	0.31202 (16)	0.70268 (13)	0.0224 (3)
H7A	0.3519	0.2466	0.7175	0.027*
C8	0.42914 (17)	0.44468 (15)	0.77391 (13)	0.0198 (3)
H8A	0.3871	0.4718	0.8383	0.024*
C9	0.51223 (16)	0.53929 (14)	0.74974 (11)	0.0162 (3)
C10	0.57862 (16)	0.49972 (15)	0.65532 (12)	0.0170 (3)
C11	0.6242 (2)	0.90990 (16)	0.88527 (14)	0.0281 (3)
H11A	0.6032	0.9096	0.9541	0.042*
H11B	0.5467	0.9568	0.8566	0.042*
H11C	0.7317	0.9563	0.8995	0.042*
N10	0.78866 (14)	0.34235 (12)	0.84378 (10)	0.0162 (2)
H10A	0.7189	0.3184	0.8753	0.019*
C20	0.82760 (17)	0.24663 (15)	0.75829 (12)	0.0191 (3)
C30	0.93774 (18)	0.28098 (17)	0.70558 (13)	0.0229 (3)
H30A	0.9664	0.2135	0.6446	0.027*
C40	1.00298 (17)	0.41161 (17)	0.74252 (13)	0.0228 (3)
H40A	1.0768	0.4355	0.7065	0.027*
C50	1.02523 (18)	0.65023 (17)	0.87842 (14)	0.0243 (3)
H50A	1.1020	0.6795	0.8472	0.029*
C60	0.97663 (19)	0.74209 (17)	0.96617 (14)	0.0260 (3)
H60A	1.0208	0.8343	0.9950	0.031*
C70	0.86274 (18)	0.70242 (16)	1.01421 (13)	0.0224 (3)
H70A	0.8297	0.7678	1.0742	0.027*
C80	0.79985 (17)	0.57026 (15)	0.97481 (12)	0.0184 (3)
H80A	0.7232	0.5426	1.0070	0.022*
C90	0.85035 (16)	0.47527 (15)	0.88546 (12)	0.0160 (3)
C100	0.96212 (16)	0.51303 (16)	0.83449 (12)	0.0187 (3)
C110	0.7525 (2)	0.10631 (16)	0.72199 (14)	0.0253 (3)
H11G	0.6571	0.1060	0.7516	0.038*
H11D	0.8276	0.0564	0.7491	0.038*
H11E	0.7230	0.0634	0.6412	0.038*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe1	0.01678 (11)	0.01690 (11)	0.01696 (11)	0.00270 (8)	0.00541 (8)	0.00684 (8)
Cl1	0.0320 (2)	0.01997 (17)	0.0296 (2)	0.00829 (14)	0.01374 (16)	0.01273 (15)
Cl2	0.0433 (2)	0.02261 (18)	0.01708 (18)	0.00205 (16)	0.00789 (16)	0.00408 (15)
Cl3	0.0189 (3)	0.0457 (10)	0.0194 (3)	0.0106 (4)	0.00687 (19)	0.0144 (3)
Cl4	0.0341 (2)	0.02223 (19)	0.0443 (2)	−0.00335 (15)	0.01996 (19)	0.01074 (18)
Cl5	0.02390 (18)	0.02347 (17)	0.02109 (17)	0.00315 (13)	0.01329 (14)	0.01004 (14)
N1	0.0184 (6)	0.0210 (6)	0.0145 (6)	0.0025 (5)	0.0054 (5)	0.0085 (5)
C2	0.0196 (7)	0.0220 (7)	0.0185 (7)	0.0008 (5)	0.0036 (5)	0.0097 (6)
C3	0.0248 (7)	0.0254 (7)	0.0216 (7)	0.0004 (6)	0.0073 (6)	0.0131 (6)
C4	0.0202 (7)	0.0280 (8)	0.0166 (7)	0.0036 (6)	0.0063 (6)	0.0103 (6)
C5	0.0195 (7)	0.0240 (7)	0.0169 (7)	0.0067 (6)	0.0041 (5)	0.0067 (6)
C6	0.0204 (7)	0.0203 (7)	0.0237 (8)	0.0041 (6)	0.0018 (6)	0.0071 (6)
C7	0.0178 (7)	0.0226 (7)	0.0276 (8)	−0.0001 (5)	0.0028 (6)	0.0124 (6)
C8	0.0174 (7)	0.0246 (7)	0.0205 (7)	0.0027 (5)	0.0056 (5)	0.0118 (6)
C9	0.0126 (6)	0.0205 (7)	0.0151 (6)	0.0017 (5)	0.0004 (5)	0.0080 (6)
C10	0.0141 (6)	0.0225 (7)	0.0156 (6)	0.0039 (5)	0.0024 (5)	0.0092 (6)
C11	0.0385 (9)	0.0224 (8)	0.0243 (8)	−0.0009 (7)	0.0112 (7)	0.0092 (7)
N10	0.0137 (5)	0.0214 (6)	0.0179 (6)	0.0044 (4)	0.0072 (4)	0.0108 (5)
C20	0.0166 (7)	0.0250 (7)	0.0191 (7)	0.0060 (5)	0.0054 (5)	0.0114 (6)
C30	0.0200 (7)	0.0328 (8)	0.0209 (7)	0.0084 (6)	0.0106 (6)	0.0130 (7)
C40	0.0151 (7)	0.0390 (9)	0.0224 (7)	0.0051 (6)	0.0075 (6)	0.0195 (7)
C50	0.0177 (7)	0.0315 (8)	0.0299 (8)	−0.0005 (6)	0.0032 (6)	0.0204 (7)
C60	0.0228 (8)	0.0249 (8)	0.0310 (9)	−0.0016 (6)	−0.0004 (6)	0.0154 (7)
C70	0.0220 (7)	0.0233 (7)	0.0215 (7)	0.0057 (6)	0.0024 (6)	0.0095 (6)
C80	0.0153 (6)	0.0234 (7)	0.0198 (7)	0.0043 (5)	0.0047 (5)	0.0116 (6)
C90	0.0123 (6)	0.0224 (7)	0.0171 (7)	0.0040 (5)	0.0030 (5)	0.0119 (6)
C100	0.0129 (6)	0.0286 (8)	0.0205 (7)	0.0036 (5)	0.0036 (5)	0.0161 (6)
C110	0.0288 (8)	0.0227 (7)	0.0264 (8)	0.0064 (6)	0.0123 (7)	0.0089 (6)

Geometric parameters (Å, º)

Fe1—Cl1	2.204 (1)	C11—H11B	0.9800
Fe1—Cl2	2.204 (1)	C11—H11C	0.9800
Fe1—Cl3	2.191 (1)	N10—C20	1.332 (2)
Fe1—Cl31	2.15 (1)	N10—C90	1.364 (2)
Fe1—Cl4	2.180 (1)	N10—H10A	0.8800
N1—C2	1.320 (2)	C20—C30	1.402 (2)
N1—C9	1.369 (2)	C20—C110	1.477 (2)
N1—H1A	0.8800	C30—C40	1.357 (2)
C2—C3	1.413 (2)	C30—H30A	0.9500
C2—C11	1.485 (2)	C40—C100	1.421 (2)
C3—C4	1.361 (2)	C40—H40A	0.9500
C3—H3A	0.9500	C50—C60	1.373 (3)
C4—C10	1.405 (2)	C50—C100	1.406 (2)
C4—H4A	0.9500	C50—H50A	0.9500
C5—C6	1.361 (2)	C60—C70	1.406 (2)
C5—C10	1.415 (2)	C60—H60A	0.9500
C5—H5A	0.9500	C70—C80	1.362 (2)
C6—C7	1.411 (2)	C70—H70A	0.9500
C6—H6A	0.9500	C80—C90	1.409 (2)
C7—C8	1.367 (2)	C80—H80A	0.9500
C7—H7A	0.9500	C90—C100	1.4116 (19)
C8—C9	1.395 (2)	C110—H11G	0.9800
C8—H8A	0.9500	C110—H11D	0.9800
C9—C10	1.416 (2)	C110—H11E	0.9800
C11—H11A	0.9800
Cl1—Fe1—Cl2	109.64 (3)	C2—C11—H11B	109.5
Cl1—Fe1—Cl3	108.88 (10)	H11A—C11—H11B	109.5
Cl1—Fe1—Cl4	108.77 (3)	C2—C11—H11C	109.5
Cl2—Fe1—Cl3	108.22 (4)	H11A—C11—H11C	109.5
Cl2—Fe1—Cl4	111.03 (4)	H11B—C11—H11C	109.5
Cl3—Fe1—Cl4	110.27 (8)	C20—N10—C90	123.99 (13)
Cl31—Fe1—Cl4	100.7 (6)	C20—N10—H10A	118.0
Cl31—Fe1—Cl3	11.6 (5)	C90—N10—H10A	118.0
Cl31—Fe1—Cl2	107.1 (3)	N10—C20—C30	119.67 (14)
Cl31—Fe1—Cl1	119.3 (5)	N10—C20—C110	118.42 (13)
C2—N1—C9	123.72 (13)	C30—C20—C110	121.91 (14)
C2—N1—H1A	118.1	C40—C30—C20	119.35 (15)
C9—N1—H1A	118.1	C40—C30—H30A	120.3
N1—C2—C3	118.42 (14)	C20—C30—H30A	120.3
N1—C2—C11	117.88 (14)	C30—C40—C100	120.68 (14)
C3—C2—C11	123.70 (14)	C30—C40—H40A	119.7
C4—C3—C2	120.84 (14)	C100—C40—H40A	119.7
C4—C3—H3A	119.6	C60—C50—C100	120.43 (14)
C2—C3—H3A	119.6	C60—C50—H50A	119.8
C3—C4—C10	120.06 (14)	C100—C50—H50A	119.8
C3—C4—H4A	120.0	C50—C60—C70	121.35 (15)
C10—C4—H4A	120.0	C50—C60—H60A	119.3
C6—C5—C10	119.49 (14)	C70—C60—H60A	119.3
C6—C5—H5A	120.3	C80—C70—C60	120.06 (15)
C10—C5—H5A	120.3	C80—C70—H70A	120.0
C5—C6—C7	120.80 (15)	C60—C70—H70A	120.0
C5—C6—H6A	119.6	C70—C80—C90	118.88 (14)
C7—C6—H6A	119.6	C70—C80—H80A	120.6
C8—C7—C6	121.36 (14)	C90—C80—H80A	120.6
C8—C7—H7A	119.3	N10—C90—C80	120.19 (13)
C6—C7—H7A	119.3	N10—C90—C100	117.71 (13)
C7—C8—C9	118.40 (14)	C80—C90—C100	122.09 (14)
C7—C8—H8A	120.8	C50—C100—C90	117.18 (14)
C9—C8—H8A	120.8	C50—C100—C40	124.23 (14)
N1—C9—C8	119.79 (13)	C90—C100—C40	118.59 (14)
N1—C9—C10	118.89 (13)	C20—C110—H11G	109.5
C8—C9—C10	121.30 (14)	C20—C110—H11D	109.5
C4—C10—C5	123.31 (14)	H11G—C110—H11D	109.5
C4—C10—C9	118.06 (14)	C20—C110—H11E	109.5
C5—C10—C9	118.63 (13)	H11G—C110—H11E	109.5
C2—C11—H11A	109.5	H11D—C110—H11E	109.5
C9—N1—C2—C3	−0.4 (2)	C90—N10—C20—C30	−0.3 (2)
C9—N1—C2—C11	179.81 (14)	C90—N10—C20—C110	179.60 (13)
N1—C2—C3—C4	−0.9 (2)	N10—C20—C30—C40	−0.1 (2)
C11—C2—C3—C4	178.87 (15)	C110—C20—C30—C40	−179.99 (14)
C2—C3—C4—C10	1.3 (2)	C20—C30—C40—C100	0.7 (2)
C10—C5—C6—C7	−1.2 (2)	C100—C50—C60—C70	−0.3 (2)
C5—C6—C7—C8	0.4 (2)	C50—C60—C70—C80	0.9 (2)
C6—C7—C8—C9	0.9 (2)	C60—C70—C80—C90	−0.3 (2)
C2—N1—C9—C8	179.86 (14)	C20—N10—C90—C80	178.67 (13)
C2—N1—C9—C10	1.2 (2)	C20—N10—C90—C100	0.0 (2)
C7—C8—C9—N1	179.89 (13)	C70—C80—C90—N10	−179.56 (13)
C7—C8—C9—C10	−1.5 (2)	C70—C80—C90—C100	−1.0 (2)
C3—C4—C10—C5	179.41 (14)	C60—C50—C100—C90	−1.0 (2)
C3—C4—C10—C9	−0.5 (2)	C60—C50—C100—C40	178.63 (15)
C6—C5—C10—C4	−179.25 (14)	N10—C90—C100—C50	−179.80 (12)
C6—C5—C10—C9	0.7 (2)	C80—C90—C100—C50	1.6 (2)
N1—C9—C10—C4	−0.75 (19)	N10—C90—C100—C40	0.60 (19)
C8—C9—C10—C4	−179.37 (13)	C80—C90—C100—C40	−178.01 (13)
N1—C9—C10—C5	179.34 (13)	C30—C40—C100—C50	179.44 (14)
C8—C9—C10—C5	0.7 (2)	C30—C40—C100—C90	−1.0 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl5^i	0.88	2.20	3.059 (2)	165
N10—H10A···Cl5	0.88	2.16	3.042 (2)	178
C30—H30A···Cl3	0.95	2.78	3.566 (2)	140

Symmetry code: (i) −x+1, −y+1, −z+2.