Crystal structure of tris-(1,3-dimesityl-4,5-di-hydro-1H-imidazol-3-ium) tetra-bromido-cobaltate(II) bromide chloro-form hexa-solvate.

In the unit cell of the title compound, (C21H27N2)3[CoBr4]Br·6CHCl3, the tetrabromidocobaltate(II) anion and the bromide anion are located on a crystallographic threefold rotation axis. For the [CoBr4](2-) group, the axis runs through one of the Br ligands and the Co(II) atom. All other structure moieties lie on general sites. Various tris-(1,3-dimesityl-4,5-di-hydro-1H-imidazol-3-ium) structures with different counter-ions have been reported. In the title compound, the N-C-N angle is 113.7 (5)°, with short C-N bond lengths of 1.297 (7) and 1.307 (7) Å. The two mesityl planes make a dihedral angle of 34.6 (1)° and the dihedral angles between the mesityl and N-C-N planes are 82.0 (1) and 88.5 (1)°, respectively. The imidazoline ring is almost planar, with atom deviations in the range 0.003 (5)-0.017 (5) Å from the best plane; the mean deviation is 0.012 (5) Å. In the crystal, non-covalent inter-actions of the C-H⋯Br type occur between the Br(-) anion and the cation, as well as between the [CoBr4](2-) anion and both the chloro-form solvent mol-ecules. These H⋯A distances are slightly shorter than the sum of van der Waals radii.

Related literature

For similar tris­(1,3-dimesityl-4,5-di­hydro-1H-imidazol-3-ium) structures, see: Arduengo et al. (1995 ▸); Hagos et al. (2008 ▸); Santoro et al. (2013 ▸); Buchalski et al. (2015 ▸). For synthesis of 2-bromo-1,3-dimesityl-4,5-di­hydro-1H-imidazol-3-ium bromide, see: Wiggins et al. (2012 ▸). For the application of 1,3-dimesityl-4,5-di­hydro-1H-imidazol-3-ium cation as a carbene precursor, see: Díez-González et al. (2009 ▸). For catalytic application of imidazolium based [CoCl4]2− salts, see: Bica & Gärtner (2008 ▸); Wang et al. (2015 ▸).

Experimental

Crystal data

(C21H27N2)3[CoBr4]Br·6CHCl3

M = 2097.02

Trigonal,

a = 16.0535 (14) Å

c = 61.790 (12) Å

V = 13791 (4) Å3

Z = 6

Mo Kα radiation

μ = 2.92 mm−1

T = 130 K

0.22 × 0.21 × 0.20 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▸) T min = 0.279, T max = 1.0

41734 measured reflections

7309 independent reflections

4427 reflections with I > 2σ(I)

R int = 0.077

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.078

S = 0.79

7309 reflections

306 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.65 e Å−3

Δρmin = −0.65 e Å−3

Absolute structure: Flack (1983 ▸), 1821 Friedel pairs

Absolute structure parameter: 0.020 (11)

Data collection: SMART (Bruker, 2002 ▸); cell refinement: SAINT (Bruker, 2002 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015 ▸); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and local programs.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S2056989015016254/nr2061sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015016254/nr2061Isup2.hkl

Click here for additional data file.

. DOI: 10.1107/S2056989015016254/nr2061fig1.tif

Mol­ecular structure of the title compound with anisotropic displacement ellipsoids drawn at the 50% probability level. Non-stoichiometric representation.

Click here for additional data file.

a . DOI: 10.1107/S2056989015016254/nr2061fig2.tif

Crystal packing approximately viewed along a axis with inter­molecular hydrogen bonding pattern drawn as dotted lines. n class="Disease">H-atoms not involved are omitted.

CCDC reference: 1421420

Additional supporting information: crystallographic information; 3D view; checkCIF report

(C21H27N2)3[CoBr4]Br·6CHCl3	Dx = 1.515 Mg m−3
Mr = 2097.02	Mo Kα radiation, λ = 0.71073 Å
Trigonal, R3c:H	Cell parameters from 4234 reflections
a = 16.0535 (14) Å	θ = 2.5–19.7°
c = 61.790 (12) Å	µ = 2.92 mm−1
V = 13791 (4) Å3	T = 130 K
Z = 6	Prism, pale-green
F(000) = 6306	0.22 × 0.21 × 0.20 mm

Bruker SMART APEX diffractometer	7309 independent reflections
Radiation source: sealed tube	4427 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.077
φ and ω scans	θmax = 27.9°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −21→21
Tmin = 0.279, Tmax = 1.0	k = −21→19
41734 measured reflections	l = −81→81

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040	H-atom parameters constrained
wR(F2) = 0.078	w = 1/[σ2(Fo2) + (0.0298P)2] where P = (Fo2 + 2Fc2)/3
S = 0.79	(Δ/σ)max = 0.001
7309 reflections	Δρmax = 0.65 e Å−3
306 parameters	Δρmin = −0.64 e Å−3
1 restraint	Absolute structure: Flack (1983), 1821 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.020 (11)

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.

	x	y	z	Uiso*/Ueq
Co1	0.6667	0.3333	0.91225 (2)	0.0290 (3)
Br1	0.77035 (4)	0.49648 (5)	0.92389 (2)	0.04336 (19)
Br2	0.6667	0.3333	0.87362 (2)	0.0630 (4)
Br3	0.3333	0.6667	0.91594 (3)	0.0524 (4)
N1	0.4682 (3)	−0.0461 (3)	0.90279 (8)	0.0296 (12)
N2	0.4612 (3)	−0.0455 (3)	0.93802 (8)	0.0281 (12)
C1	0.4610 (4)	−0.0918 (4)	0.92081 (10)	0.0292 (14)
H1A	0.4561	−0.1533	0.9213	0.035*
C2	0.4754 (4)	0.0476 (4)	0.90750 (10)	0.0338 (16)
H2A	0.4225	0.0526	0.9005	0.041*
H2B	0.5378	0.1017	0.9026	0.041*
C3	0.4669 (4)	0.0462 (4)	0.93224 (9)	0.0270 (14)
H3A	0.5239	0.1015	0.9389	0.032*
H3B	0.4082	0.0472	0.9368	0.032*
C4	0.4725 (4)	−0.0782 (4)	0.88091 (10)	0.0319 (15)
C5	0.5614 (5)	−0.0511 (5)	0.87196 (13)	0.049 (2)
C6	0.5625 (6)	−0.0800 (5)	0.85046 (12)	0.055 (2)
H6A	0.6222	−0.0621	0.8437	0.065*
C7	0.4769 (7)	−0.1346 (6)	0.83901 (12)	0.054 (2)
C8	0.3921 (6)	−0.1592 (5)	0.84898 (11)	0.0464 (18)
H8A	0.3340	−0.1964	0.8412	0.056*
C9	0.3867 (5)	−0.1327 (4)	0.86980 (11)	0.0375 (16)
C10	0.6534 (5)	0.0048 (6)	0.88517 (16)	0.087 (3)
H10A	0.6525	−0.0346	0.8974	0.130*
H10B	0.6577	0.0641	0.8907	0.130*
H10C	0.7092	0.0210	0.8760	0.130*
C11	0.4845 (7)	−0.1602 (6)	0.81586 (12)	0.080 (3)
H11A	0.5414	−0.1673	0.8143	0.120*
H11B	0.4902	−0.1090	0.8062	0.120*
H11C	0.4268	−0.2209	0.8120	0.120*
C12	0.2910 (5)	−0.1610 (5)	0.87956 (12)	0.0503 (19)
H12A	0.2405	−0.1947	0.8687	0.075*
H12B	0.2902	−0.1032	0.8844	0.075*
H12C	0.2795	−0.2035	0.8919	0.075*
C13	0.4495 (4)	−0.0797 (4)	0.96013 (10)	0.0293 (14)
C14	0.5308 (4)	−0.0439 (4)	0.97348 (11)	0.0356 (16)
C15	0.5164 (5)	−0.0718 (4)	0.99472 (11)	0.0395 (17)
H15A	0.5707	−0.0479	1.0040	0.047*
C16	0.4255 (5)	−0.1339 (4)	1.00332 (11)	0.0403 (17)
C17	0.3468 (5)	−0.1667 (5)	0.98966 (12)	0.0454 (19)
H17A	0.2845	−0.2091	0.9953	0.055*
C18	0.3559 (5)	−0.1394 (4)	0.96770 (12)	0.0378 (16)
C19	0.6300 (4)	0.0195 (5)	0.96462 (11)	0.0487 (19)
H19A	0.6332	0.0760	0.9577	0.073*
H19B	0.6447	−0.0163	0.9539	0.073*
H19C	0.6769	0.0403	0.9764	0.073*
C20	0.4143 (6)	−0.1603 (5)	1.02691 (12)	0.059 (2)
H20A	0.4242	−0.2153	1.0290	0.089*
H20B	0.3495	−0.1774	1.0317	0.089*
H20C	0.4620	−0.1054	1.0354	0.089*
C21	0.2699 (4)	−0.1763 (5)	0.95317 (12)	0.0503 (19)
H21A	0.2725	−0.2195	0.9423	0.076*
H21B	0.2698	−0.1221	0.9459	0.076*
H21C	0.2111	−0.2116	0.9618	0.076*
C100	0.8893 (6)	0.1327 (6)	0.92865 (13)	0.070 (3)
H10	0.8362	0.1455	0.9248	0.084*
Cl11	0.91290 (19)	0.1546 (2)	0.95548 (4)	0.0938 (8)
Cl12	0.8521 (2)	0.0149 (2)	0.92250 (7)	0.1562 (18)
Cl13	0.9911 (3)	0.2121 (2)	0.91398 (5)	0.1293 (12)
C200	0.0704 (6)	0.8507 (6)	0.01629 (18)	0.091 (3)
H20	0.0749	0.9066	0.0245	0.109*
Cl21	0.1365 (2)	0.8900 (2)	−0.00698 (6)	0.1410 (14)
Cl22	0.11836 (19)	0.7912 (2)	0.03238 (5)	0.1032 (9)
Cl23	−0.05036 (16)	0.76626 (15)	0.01124 (4)	0.0790 (7)

	U11	U22	U33	U12	U13	U23
Co1	0.0214 (5)	0.0214 (5)	0.0440 (10)	0.0107 (2)	0.000	0.000
Br1	0.0253 (3)	0.0267 (3)	0.0769 (5)	0.0121 (3)	−0.0062 (4)	−0.0129 (3)
Br2	0.0687 (6)	0.0687 (6)	0.0515 (9)	0.0344 (3)	0.000	0.000
Br3	0.0263 (4)	0.0263 (4)	0.1045 (11)	0.01314 (19)	0.000	0.000
N1	0.030 (3)	0.027 (3)	0.033 (3)	0.015 (2)	−0.001 (2)	−0.004 (2)
N2	0.032 (3)	0.026 (3)	0.028 (3)	0.016 (2)	0.003 (2)	0.000 (2)
C1	0.023 (3)	0.024 (3)	0.034 (4)	0.007 (3)	0.002 (3)	0.002 (3)
C2	0.032 (4)	0.025 (3)	0.046 (5)	0.015 (3)	−0.004 (3)	−0.004 (3)
C3	0.031 (3)	0.027 (3)	0.027 (4)	0.017 (3)	−0.001 (3)	−0.005 (3)
C4	0.041 (4)	0.024 (3)	0.031 (4)	0.016 (3)	0.004 (3)	0.004 (3)
C5	0.051 (5)	0.034 (4)	0.065 (6)	0.023 (4)	0.013 (4)	−0.001 (4)
C6	0.072 (6)	0.049 (5)	0.056 (6)	0.041 (4)	0.036 (5)	0.017 (4)
C7	0.092 (6)	0.056 (5)	0.037 (5)	0.055 (5)	−0.005 (5)	−0.002 (4)
C8	0.062 (5)	0.056 (5)	0.029 (4)	0.034 (4)	−0.001 (4)	−0.007 (4)
C9	0.052 (4)	0.032 (4)	0.031 (4)	0.023 (3)	−0.005 (3)	−0.003 (3)
C10	0.029 (4)	0.098 (7)	0.125 (9)	0.026 (5)	0.007 (5)	−0.044 (6)
C11	0.149 (9)	0.094 (7)	0.044 (6)	0.095 (7)	0.010 (5)	0.005 (5)
C12	0.043 (4)	0.047 (4)	0.050 (5)	0.014 (4)	−0.009 (4)	−0.015 (4)
C13	0.037 (4)	0.020 (3)	0.032 (4)	0.015 (3)	0.004 (3)	0.002 (3)
C14	0.039 (4)	0.027 (3)	0.039 (5)	0.015 (3)	0.001 (3)	0.010 (3)
C15	0.047 (4)	0.040 (4)	0.035 (5)	0.024 (4)	0.000 (3)	0.007 (3)
C16	0.060 (5)	0.034 (4)	0.034 (4)	0.030 (4)	0.005 (4)	0.004 (3)
C17	0.052 (5)	0.036 (4)	0.045 (5)	0.021 (4)	0.028 (4)	0.011 (4)
C18	0.041 (4)	0.027 (4)	0.046 (5)	0.017 (3)	0.005 (3)	−0.005 (3)
C19	0.034 (4)	0.050 (4)	0.050 (5)	0.012 (4)	−0.001 (3)	0.007 (4)
C20	0.073 (6)	0.052 (5)	0.052 (5)	0.030 (4)	0.019 (4)	0.021 (4)
C21	0.035 (4)	0.050 (4)	0.058 (5)	0.015 (4)	0.011 (4)	0.000 (4)
C100	0.076 (6)	0.086 (6)	0.074 (7)	0.061 (6)	−0.032 (5)	−0.030 (5)
Cl11	0.106 (2)	0.119 (2)	0.0673 (17)	0.0651 (18)	−0.0027 (14)	0.0048 (15)
Cl12	0.159 (3)	0.107 (2)	0.248 (5)	0.101 (2)	−0.115 (3)	−0.096 (3)
Cl13	0.192 (3)	0.165 (3)	0.115 (2)	0.153 (3)	0.073 (2)	0.067 (2)
C200	0.061 (6)	0.049 (5)	0.147 (10)	0.016 (5)	0.028 (6)	−0.021 (6)
Cl21	0.128 (3)	0.114 (2)	0.181 (4)	0.060 (2)	0.098 (3)	0.067 (2)
Cl22	0.096 (2)	0.0933 (19)	0.107 (2)	0.0379 (16)	−0.0029 (17)	−0.0331 (17)
Cl23	0.0694 (15)	0.0597 (14)	0.0825 (17)	0.0131 (12)	0.0122 (13)	−0.0093 (12)

Co1—Br2	2.387 (2)	C11—H11C	0.9800
Co1—Br1	2.4057 (8)	C12—H12A	0.9800
Co1—Br1i	2.4057 (8)	C12—H12B	0.9800
Co1—Br1ii	2.4057 (8)	C12—H12C	0.9800
N1—C1	1.307 (7)	C13—C18	1.397 (8)
N1—C4	1.460 (7)	C13—C14	1.402 (8)
N1—C2	1.479 (7)	C14—C15	1.368 (8)
N2—C1	1.297 (7)	C14—C19	1.500 (8)
N2—C13	1.449 (7)	C15—C16	1.397 (9)
N2—C3	1.472 (7)	C15—H15A	0.9500
C1—H1A	0.9500	C16—C17	1.386 (10)
C2—C3	1.534 (8)	C16—C20	1.504 (9)
C2—H2A	0.9900	C17—C18	1.411 (9)
C2—H2B	0.9900	C17—H17A	0.9500
C3—H3A	0.9900	C18—C21	1.499 (9)
C3—H3B	0.9900	C19—H19A	0.9800
C4—C5	1.383 (9)	C19—H19B	0.9800
C4—C9	1.389 (8)	C19—H19C	0.9800
C5—C6	1.410 (10)	C20—H20A	0.9800
C5—C10	1.525 (10)	C20—H20B	0.9800
C6—C7	1.397 (10)	C20—H20C	0.9800
C6—H6A	0.9500	C21—H21A	0.9800
C7—C8	1.360 (10)	C21—H21B	0.9800
C7—C11	1.510 (10)	C21—H21C	0.9800
C8—C9	1.371 (9)	C100—Cl11	1.698 (8)
C8—H8A	0.9500	C100—Cl12	1.716 (8)
C9—C12	1.494 (9)	C100—Cl13	1.741 (9)
C10—H10A	0.9800	C100—H10	1.0000
C10—H10B	0.9800	C200—Cl21	1.709 (10)
C10—H10C	0.9800	C200—Cl23	1.751 (9)
C11—H11A	0.9800	C200—Cl22	1.797 (11)
C11—H11B	0.9800	C200—H20	1.0000
Br2—Co1—Br1	107.39 (4)	H11B—C11—H11C	109.5
Br2—Co1—Br1i	107.39 (4)	C9—C12—H12A	109.5
Br1—Co1—Br1i	111.47 (4)	C9—C12—H12B	109.5
Br2—Co1—Br1ii	107.39 (4)	H12A—C12—H12B	109.5
Br1—Co1—Br1ii	111.47 (4)	C9—C12—H12C	109.5
Br1i—Co1—Br1ii	111.47 (4)	H12A—C12—H12C	109.5
C1—N1—C4	126.6 (5)	H12B—C12—H12C	109.5
C1—N1—C2	110.1 (5)	C18—C13—C14	123.0 (6)
C4—N1—C2	123.2 (5)	C18—C13—N2	117.9 (5)
C1—N2—C13	126.4 (5)	C14—C13—N2	118.8 (5)
C1—N2—C3	110.8 (5)	C15—C14—C13	117.4 (6)
C13—N2—C3	122.6 (5)	C15—C14—C19	121.4 (6)
N2—C1—N1	113.7 (5)	C13—C14—C19	121.2 (6)
N2—C1—H1A	123.1	C14—C15—C16	123.0 (6)
N1—C1—H1A	123.1	C14—C15—H15A	118.5
N1—C2—C3	102.7 (5)	C16—C15—H15A	118.5
N1—C2—H2A	111.2	C17—C16—C15	117.9 (6)
C3—C2—H2A	111.2	C17—C16—C20	121.7 (6)
N1—C2—H2B	111.2	C15—C16—C20	120.3 (7)
C3—C2—H2B	111.2	C16—C17—C18	122.3 (6)
H2A—C2—H2B	109.1	C16—C17—H17A	118.9
N2—C3—C2	102.5 (4)	C18—C17—H17A	118.9
N2—C3—H3A	111.3	C13—C18—C17	116.4 (6)
C2—C3—H3A	111.3	C13—C18—C21	122.2 (6)
N2—C3—H3B	111.3	C17—C18—C21	121.4 (6)
C2—C3—H3B	111.3	C14—C19—H19A	109.5
H3A—C3—H3B	109.2	C14—C19—H19B	109.5
C5—C4—C9	122.9 (6)	H19A—C19—H19B	109.5
C5—C4—N1	118.9 (6)	C14—C19—H19C	109.5
C9—C4—N1	118.2 (5)	H19A—C19—H19C	109.5
C4—C5—C6	117.0 (7)	H19B—C19—H19C	109.5
C4—C5—C10	121.0 (7)	C16—C20—H20A	109.5
C6—C5—C10	122.0 (7)	C16—C20—H20B	109.5
C7—C6—C5	120.9 (7)	H20A—C20—H20B	109.5
C7—C6—H6A	119.5	C16—C20—H20C	109.5
C5—C6—H6A	119.5	H20A—C20—H20C	109.5
C8—C7—C6	118.7 (7)	H20B—C20—H20C	109.5
C8—C7—C11	123.7 (8)	C18—C21—H21A	109.5
C6—C7—C11	117.5 (8)	C18—C21—H21B	109.5
C7—C8—C9	123.0 (7)	H21A—C21—H21B	109.5
C7—C8—H8A	118.5	C18—C21—H21C	109.5
C9—C8—H8A	118.5	H21A—C21—H21C	109.5
C8—C9—C4	117.6 (6)	H21B—C21—H21C	109.5
C8—C9—C12	119.9 (6)	Cl11—C100—Cl12	111.3 (5)
C4—C9—C12	122.5 (6)	Cl11—C100—Cl13	109.0 (5)
C5—C10—H10A	109.5	Cl12—C100—Cl13	112.0 (5)
C5—C10—H10B	109.5	Cl11—C100—H10	108.1
H10A—C10—H10B	109.5	Cl12—C100—H10	108.1
C5—C10—H10C	109.5	Cl13—C100—H10	108.1
H10A—C10—H10C	109.5	Cl21—C200—Cl23	112.2 (6)
H10B—C10—H10C	109.5	Cl21—C200—Cl22	108.1 (5)
C7—C11—H11A	109.5	Cl23—C200—Cl22	106.8 (5)
C7—C11—H11B	109.5	Cl21—C200—H20	109.9
H11A—C11—H11B	109.5	Cl23—C200—H20	109.9
C7—C11—H11C	109.5	Cl22—C200—H20	109.9
H11A—C11—H11C	109.5
C13—N2—C1—N1	176.7 (5)	C5—C4—C9—C8	−0.7 (9)
C3—N2—C1—N1	1.7 (7)	N1—C4—C9—C8	177.6 (5)
C4—N1—C1—N2	178.3 (5)	C5—C4—C9—C12	−179.5 (6)
C2—N1—C1—N2	0.4 (7)	N1—C4—C9—C12	−1.2 (9)
C1—N1—C2—C3	−2.2 (6)	C1—N2—C13—C18	−82.7 (7)
C4—N1—C2—C3	179.9 (5)	C3—N2—C13—C18	91.8 (7)
C1—N2—C3—C2	−2.9 (6)	C1—N2—C13—C14	103.6 (7)
C13—N2—C3—C2	−178.1 (5)	C3—N2—C13—C14	−81.9 (7)
N1—C2—C3—N2	2.8 (5)	C18—C13—C14—C15	1.8 (9)
C1—N1—C4—C5	−91.4 (7)	N2—C13—C14—C15	175.0 (5)
C2—N1—C4—C5	86.2 (7)	C18—C13—C14—C19	179.6 (6)
C1—N1—C4—C9	90.3 (7)	N2—C13—C14—C19	−7.1 (9)
C2—N1—C4—C9	−92.1 (7)	C13—C14—C15—C16	0.5 (9)
C9—C4—C5—C6	1.1 (9)	C19—C14—C15—C16	−177.3 (6)
N1—C4—C5—C6	−177.2 (5)	C14—C15—C16—C17	−1.3 (10)
C9—C4—C5—C10	−177.1 (7)	C14—C15—C16—C20	−178.8 (6)
N1—C4—C5—C10	4.6 (10)	C15—C16—C17—C18	−0.1 (9)
C4—C5—C6—C7	−0.8 (10)	C20—C16—C17—C18	177.3 (6)
C10—C5—C6—C7	177.3 (7)	C14—C13—C18—C17	−3.0 (9)
C5—C6—C7—C8	0.3 (10)	N2—C13—C18—C17	−176.4 (5)
C5—C6—C7—C11	178.3 (6)	C14—C13—C18—C21	179.7 (6)
C6—C7—C8—C9	0.1 (11)	N2—C13—C18—C21	6.3 (9)
C11—C7—C8—C9	−177.8 (6)	C16—C17—C18—C13	2.2 (9)
C7—C8—C9—C4	0.1 (10)	C16—C17—C18—C21	179.5 (6)
C7—C8—C9—C12	178.9 (6)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···Br3iii	0.95	2.58	3.373 (4)	141
C100—H10···Br1i	1.00	2.71	3.668 (5)	161
C200—H20···Br2iv	1.00	2.54	3.454 (6)	152

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
C1H1ABr3ii	0.95	2.58	3.373(4)	141
C100H10Br1i	1.00	2.71	3.668(5)	161
C200H20Br2iii	1.00	2.54	3.454(6)	152

Symmetry codes: (i) ; (ii) ; (iii) .