2-Methyl­propan-2-aminium 3,4,5,6-tetra­bromo-2-(meth­oxy­carbon­yl)benzoate methanol monosolvate

Li, J.

doi:10.1107/S1600536811008518

organic compounds

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Volume 67| Part 4| April 2011| Page o869

doi:10.1107/S1600536811008518

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2-Methylpropan-2-aminium 3,4,5,6-tetrabromo-2-(methoxycarbonyl)benzoate methanol monosolvate

Jian Li ^a ^*

^aDepartment of Chemistry and Chemical Engineering, Weifang University, Weifang 261061, People's Republic of China
^*Correspondence e-mail: ljwfu@163.com

(Received 18 January 2011; accepted 6 March 2011; online 12 March 2011)

In the crystal structure of the title compound, C₄H₁₂N⁺·C₉H₃Br₄O₄⁻·CH₄O, intermolecular O—H⋯O, N—H⋯O and C—H⋯O hydrogen bonds link the components into columns stacked along the b axis. Between the columns, short Br⋯O contacts [3.122 (4) Å] and C—H⋯O hydrogen bonds are observed.

Related literature

For related structures, see: Li (2011 ); Liang (2008 ).

Experimental

Crystal data

C₄H₁₂N⁺·C₉H₃Br₄O₄⁻·CH₄O
M_r = 600.94
Monoclinic, P 2₁ /c
a = 12.3832 (11) Å
b = 8.4001 (6) Å
c = 20.6394 (18) Å
β = 107.316 (1)°
V = 2049.6 (3) Å³
Z = 4
Mo Kα radiation
μ = 7.88 mm⁻¹
T = 298 K
0.39 × 0.30 × 0.24 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1997 ) T_min = 0.149, T_max = 0.254
9926 measured reflections
3597 independent reflections
2071 reflections with I > 2σ(I)
R_int = 0.062

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.072
S = 1.06
3597 reflections
217 parameters
H-atom parameters constrained
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.52 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O4ⁱ	0.89	1.91	2.775 (6)	162
N1—H1B⋯O3	0.89	2.03	2.916 (6)	177
N1—H1C⋯O5ⁱⁱ	0.89	1.96	2.837 (6)	168
O5—H5⋯O3	0.82	1.91	2.723 (6)	168
C13—H13C⋯O2ⁱⁱⁱ	0.96	2.58	3.491 (8)	158
C20—H20B⋯O2^iv	0.96	2.57	3.449 (8)	153
Symmetry codes: (i) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) x, y+1, z; (iv) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811008518/is2668sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811008518/is2668Isup2.hkl

checkCIF report

Comment top

4,5,6,7-Tetrabromo-2-ethylisoindoline-1,3-dione is an important flame retardant. 2-(Methoxycarbonyl)-3,4,5,6-tetrabromobenzoic acid is the intermediate of the flame retardant.

In this paper, the structure of the title compound is reported (Fig. 1). The bond lengths and angles agree with those in the similar compounds (Liang, 2008; Li, 2011). The crystal structure is stabilized by N—H···O hydrogen bonds between the 2-methylpropan-2-aminium cation and the 2-(methoxycarbonyl)-3,4,5,6-tetrabromobenzoate anion, and by O—H···O and N—H···O hydrogen bonds between methanol, 2-(methoxycarbonyl)-3,4,5,6-tetrabromobenzoate and 2-methylpropan-2-aminium (Table 1 and Fig. 2).

Related literature top

For related structures, see: Li (2011); Liang (2008).

Experimental top

A mixture of 4,5,6,7-tetrabromoisobenzofuran-1,3-dione (4.64 g, 0.01 mol) and methanol (15 ml) was refluxed for 0.5 h. Ethanamine (0.73 g, 0.01 mol) was then added to the above solution, being mixed round for 10 min at room temperature. The solution was kept at room temperature for 5 d. Natural evaporation gave colourless single crystals of the title compound suitable for X-ray analysis.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with 30% probability ellipsoids.
	Fig. 2. A packing diagram, viewed along the b axis.

2-Methylpropan-2-aminium 3,4,5,6-tetrabromo-2-(methoxycarbonyl)benzoate methanol monosolvate top

Crystal data top

C₄H₁₂N⁺·C₉H₃Br₄O₄⁻·CH₄O	F(000) = 1160
M_r = 600.94	D_x = 1.947 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1758 reflections
a = 12.3832 (11) Å	θ = 2.6–22.7°
b = 8.4001 (6) Å	µ = 7.88 mm⁻¹
c = 20.6394 (18) Å	T = 298 K
β = 107.316 (1)°	Block, colorless
V = 2049.6 (3) Å³	0.39 × 0.30 × 0.24 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	3597 independent reflections
Radiation source: fine-focus sealed tube	2071 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.062
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −14→14
T_min = 0.149, T_max = 0.254	k = −9→6
9926 measured reflections	l = −24→24

Refinement top

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.072	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0138P)²] where P = (F_o² + 2F_c²)/3
3597 reflections	(Δ/σ)_max < 0.001
217 parameters	Δρ_max = 0.45 e Å⁻³
0 restraints	Δρ_min = −0.52 e Å⁻³

Crystal data top

C₄H₁₂N⁺·C₉H₃Br₄O₄⁻·CH₄O	V = 2049.6 (3) Å³
M_r = 600.94	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.3832 (11) Å	µ = 7.88 mm⁻¹
b = 8.4001 (6) Å	T = 298 K
c = 20.6394 (18) Å	0.39 × 0.30 × 0.24 mm
β = 107.316 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3597 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1997)	2071 reflections with I > 2σ(I)
T_min = 0.149, T_max = 0.254	R_int = 0.062
9926 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.072	H-atom parameters constrained
S = 1.06	Δρ_max = 0.45 e Å⁻³
3597 reflections	Δρ_min = −0.52 e Å⁻³
217 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

	x	y	z	U_iso*/U_eq
Br1	0.11686 (5)	0.40889 (8)	0.47788 (3)	0.0564 (2)
Br2	0.33036 (5)	0.29201 (9)	0.60590 (3)	0.0532 (2)
Br3	0.57304 (5)	0.20168 (9)	0.58025 (3)	0.0570 (2)
Br4	0.59859 (5)	0.23055 (9)	0.42537 (4)	0.0631 (2)
N1	−0.0325 (3)	0.4861 (5)	0.1881 (2)	0.0428 (13)
H1A	−0.0599	0.5833	0.1761	0.064*
H1B	0.0293	0.4928	0.2236	0.064*
H1C	−0.0844	0.4276	0.1991	0.064*
O1	0.4384 (3)	0.4674 (5)	0.31058 (19)	0.0504 (11)
O2	0.3379 (3)	0.2489 (5)	0.2725 (2)	0.0465 (11)
O3	0.1746 (3)	0.5145 (5)	0.3009 (2)	0.0463 (11)
O4	0.0805 (3)	0.3093 (5)	0.32508 (19)	0.0477 (11)
O5	0.2206 (3)	0.8283 (5)	0.2893 (2)	0.0663 (13)
H5	0.2158	0.7314	0.2923	0.100*
C1	0.3789 (4)	0.3409 (7)	0.3164 (3)	0.0317 (15)
C2	0.1642 (5)	0.3974 (8)	0.3359 (3)	0.0337 (14)
C3	0.3692 (4)	0.3273 (6)	0.3878 (3)	0.0329 (14)
C4	0.2644 (4)	0.3585 (6)	0.3973 (3)	0.0291 (14)
C5	0.2554 (4)	0.3503 (6)	0.4636 (3)	0.0326 (15)
C6	0.3464 (4)	0.3065 (6)	0.5185 (3)	0.0360 (14)
C7	0.4492 (4)	0.2690 (7)	0.5079 (3)	0.0374 (15)
C8	0.4596 (4)	0.2806 (7)	0.4422 (3)	0.0378 (15)
C9	−0.0030 (5)	0.4086 (7)	0.1290 (3)	0.0405 (15)
C10	−0.1117 (5)	0.4006 (8)	0.0699 (3)	0.070 (2)
H10A	−0.1402	0.5063	0.0581	0.105*
H10B	−0.1670	0.3387	0.0829	0.105*
H10C	−0.0962	0.3518	0.0315	0.105*
C11	0.0415 (5)	0.2446 (7)	0.1526 (3)	0.0512 (18)
H11A	−0.0166	0.1836	0.1630	0.077*
H11B	0.1056	0.2536	0.1924	0.077*
H11C	0.0640	0.1924	0.1172	0.077*
C12	0.0869 (5)	0.5111 (7)	0.1136 (3)	0.068 (2)
H12A	0.1526	0.5147	0.1527	0.102*
H12B	0.0581	0.6169	0.1025	0.102*
H12C	0.1071	0.4666	0.0760	0.102*
C13	0.2318 (6)	0.8673 (8)	0.2255 (4)	0.081 (2)
H13A	0.1615	0.8480	0.1911	0.122*
H13B	0.2900	0.8029	0.2168	0.122*
H13C	0.2517	0.9777	0.2250	0.122*
C20	0.4511 (5)	0.4985 (8)	0.2440 (3)	0.063 (2)
H20A	0.4884	0.4101	0.2305	0.094*
H20B	0.4953	0.5932	0.2458	0.094*
H20C	0.3778	0.5129	0.2117	0.094*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0443 (4)	0.0832 (6)	0.0473 (4)	0.0174 (4)	0.0219 (3)	0.0091 (4)
Br2	0.0511 (4)	0.0766 (5)	0.0321 (4)	−0.0041 (4)	0.0125 (3)	0.0065 (4)
Br3	0.0408 (4)	0.0761 (5)	0.0448 (4)	0.0081 (4)	−0.0018 (3)	0.0065 (4)
Br4	0.0361 (4)	0.0945 (6)	0.0611 (5)	0.0116 (4)	0.0181 (3)	0.0003 (4)
N1	0.039 (3)	0.048 (3)	0.039 (3)	0.005 (3)	0.008 (2)	0.000 (3)
O1	0.055 (3)	0.059 (3)	0.041 (3)	−0.028 (2)	0.020 (2)	−0.006 (2)
O2	0.057 (3)	0.045 (3)	0.040 (3)	−0.009 (2)	0.017 (2)	−0.014 (2)
O3	0.049 (2)	0.038 (3)	0.047 (3)	−0.001 (2)	0.008 (2)	0.019 (2)
O4	0.037 (2)	0.048 (3)	0.051 (3)	−0.013 (2)	0.003 (2)	0.004 (2)
O5	0.060 (3)	0.047 (3)	0.087 (4)	0.002 (2)	0.014 (3)	0.004 (3)
C1	0.022 (3)	0.020 (4)	0.048 (4)	0.002 (3)	0.001 (3)	−0.007 (3)
C2	0.040 (4)	0.034 (4)	0.028 (4)	0.003 (3)	0.010 (3)	−0.006 (3)
C3	0.036 (3)	0.026 (4)	0.035 (4)	−0.007 (3)	0.009 (3)	−0.005 (3)
C4	0.026 (3)	0.019 (3)	0.039 (4)	−0.005 (2)	0.006 (3)	0.005 (3)
C5	0.030 (3)	0.035 (4)	0.032 (4)	−0.001 (3)	0.008 (3)	0.006 (3)
C6	0.032 (3)	0.033 (4)	0.039 (4)	−0.004 (3)	0.005 (3)	0.006 (3)
C7	0.031 (3)	0.039 (4)	0.033 (4)	0.005 (3)	−0.004 (3)	0.000 (3)
C8	0.031 (3)	0.041 (4)	0.041 (4)	−0.002 (3)	0.009 (3)	0.001 (3)
C9	0.048 (4)	0.038 (4)	0.037 (4)	0.009 (3)	0.014 (3)	0.000 (3)
C10	0.065 (4)	0.100 (6)	0.032 (4)	0.005 (4)	−0.004 (4)	−0.002 (4)
C11	0.063 (4)	0.049 (5)	0.044 (4)	0.004 (4)	0.019 (3)	−0.009 (3)
C12	0.082 (5)	0.060 (5)	0.074 (5)	−0.004 (4)	0.043 (4)	0.008 (4)
C13	0.102 (6)	0.056 (6)	0.100 (7)	−0.015 (4)	0.051 (5)	−0.001 (5)
C20	0.076 (4)	0.071 (5)	0.050 (5)	−0.023 (4)	0.033 (4)	0.001 (4)

Geometric parameters (Å, º) top

Br1—C5	1.891 (5)	C6—C7	1.390 (7)
Br2—C6	1.878 (5)	C7—C8	1.403 (7)
Br3—C7	1.881 (5)	C9—C11	1.509 (7)
Br4—C8	1.901 (5)	C9—C12	1.514 (7)
N1—C9	1.520 (6)	C9—C10	1.526 (7)
N1—H1A	0.8900	C10—H10A	0.9600
N1—H1B	0.8900	C10—H10B	0.9600
N1—H1C	0.8900	C10—H10C	0.9600
O1—C1	1.318 (6)	C11—H11A	0.9600
O1—C20	1.452 (6)	C11—H11B	0.9600
O2—C1	1.185 (6)	C11—H11C	0.9600
O3—C2	1.250 (6)	C12—H12A	0.9600
O4—C2	1.239 (6)	C12—H12B	0.9600
O5—C13	1.402 (7)	C12—H12C	0.9600
O5—H5	0.8200	C13—H13A	0.9600
C1—C3	1.517 (7)	C13—H13B	0.9600
C2—C4	1.521 (7)	C13—H13C	0.9600
C3—C8	1.386 (7)	C20—H20A	0.9600
C3—C4	1.394 (6)	C20—H20B	0.9600
C4—C5	1.407 (7)	C20—H20C	0.9600
C5—C6	1.389 (6)

C9—N1—H1A	109.5	C12—C9—N1	107.0 (5)
C9—N1—H1B	109.5	C11—C9—C10	111.6 (5)
H1A—N1—H1B	109.5	C12—C9—C10	112.7 (5)
C9—N1—H1C	109.5	N1—C9—C10	107.1 (4)
H1A—N1—H1C	109.5	C9—C10—H10A	109.5
H1B—N1—H1C	109.5	C9—C10—H10B	109.5
C1—O1—C20	116.9 (5)	H10A—C10—H10B	109.5
C13—O5—H5	109.5	C9—C10—H10C	109.5
O2—C1—O1	125.4 (6)	H10A—C10—H10C	109.5
O2—C1—C3	123.6 (5)	H10B—C10—H10C	109.5
O1—C1—C3	111.0 (5)	C9—C11—H11A	109.5
O4—C2—O3	126.2 (5)	C9—C11—H11B	109.5
O4—C2—C4	116.9 (5)	H11A—C11—H11B	109.5
O3—C2—C4	116.8 (5)	C9—C11—H11C	109.5
C8—C3—C4	120.1 (5)	H11A—C11—H11C	109.5
C8—C3—C1	122.0 (5)	H11B—C11—H11C	109.5
C4—C3—C1	117.9 (5)	C9—C12—H12A	109.5
C3—C4—C5	118.3 (5)	C9—C12—H12B	109.5
C3—C4—C2	119.1 (5)	H12A—C12—H12B	109.5
C5—C4—C2	122.6 (5)	C9—C12—H12C	109.5
C6—C5—C4	121.8 (5)	H12A—C12—H12C	109.5
C6—C5—Br1	119.7 (4)	H12B—C12—H12C	109.5
C4—C5—Br1	118.5 (4)	O5—C13—H13A	109.5
C5—C6—C7	119.4 (5)	O5—C13—H13B	109.5
C5—C6—Br2	120.6 (4)	H13A—C13—H13B	109.5
C7—C6—Br2	120.0 (4)	O5—C13—H13C	109.5
C6—C7—C8	119.2 (5)	H13A—C13—H13C	109.5
C6—C7—Br3	120.8 (4)	H13B—C13—H13C	109.5
C8—C7—Br3	120.0 (4)	O1—C20—H20A	109.5
C3—C8—C7	121.2 (5)	O1—C20—H20B	109.5
C3—C8—Br4	118.1 (4)	H20A—C20—H20B	109.5
C7—C8—Br4	120.6 (4)	O1—C20—H20C	109.5
C11—C9—C12	111.5 (5)	H20A—C20—H20C	109.5
C11—C9—N1	106.6 (4)	H20B—C20—H20C	109.5

C20—O1—C1—O2	2.2 (8)	C2—C4—C5—Br1	−5.9 (7)
C20—O1—C1—C3	−177.8 (4)	C4—C5—C6—C7	−0.3 (8)
O2—C1—C3—C8	106.6 (7)	Br1—C5—C6—C7	−177.8 (4)
O1—C1—C3—C8	−73.4 (6)	C4—C5—C6—Br2	−178.5 (4)
O2—C1—C3—C4	−71.4 (7)	Br1—C5—C6—Br2	4.0 (6)
O1—C1—C3—C4	108.6 (5)	C5—C6—C7—C8	1.8 (8)
C8—C3—C4—C5	3.7 (8)	Br2—C6—C7—C8	180.0 (4)
C1—C3—C4—C5	−178.3 (5)	C5—C6—C7—Br3	−177.7 (4)
C8—C3—C4—C2	−175.4 (5)	Br2—C6—C7—Br3	0.5 (7)
C1—C3—C4—C2	2.6 (7)	C4—C3—C8—C7	−2.2 (8)
O4—C2—C4—C3	121.4 (6)	C1—C3—C8—C7	179.8 (5)
O3—C2—C4—C3	−57.9 (7)	C4—C3—C8—Br4	177.3 (4)
O4—C2—C4—C5	−57.7 (7)	C1—C3—C8—Br4	−0.7 (7)
O3—C2—C4—C5	123.0 (6)	C6—C7—C8—C3	−0.5 (9)
C3—C4—C5—C6	−2.5 (8)	Br3—C7—C8—C3	178.9 (4)
C2—C4—C5—C6	176.6 (5)	C6—C7—C8—Br4	180.0 (4)
C3—C4—C5—Br1	175.0 (4)	Br3—C7—C8—Br4	−0.6 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O4ⁱ	0.89	1.91	2.775 (6)	162
N1—H1B···O3	0.89	2.03	2.916 (6)	177
N1—H1C···O5ⁱⁱ	0.89	1.96	2.837 (6)	168
O5—H5···O3	0.82	1.91	2.723 (6)	168
C13—H13C···O2ⁱⁱⁱ	0.96	2.58	3.491 (8)	158
C20—H20B···O2^iv	0.96	2.57	3.449 (8)	153

Symmetry codes: (i) −x, y+1/2, −z+1/2; (ii) −x, y−1/2, −z+1/2; (iii) x, y+1, z; (iv) −x+1, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₄H₁₂N⁺·C₉H₃Br₄O₄⁻·CH₄O
M_r	600.94
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	12.3832 (11), 8.4001 (6), 20.6394 (18)
β (°)	107.316 (1)
V (Å³)	2049.6 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	7.88
Crystal size (mm)	0.39 × 0.30 × 0.24

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1997)
T_min, T_max	0.149, 0.254
No. of measured, independent and observed [I > 2σ(I)] reflections	9926, 3597, 2071
R_int	0.062
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.072, 1.06
No. of reflections	3597
No. of parameters	217
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.52

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O4ⁱ	0.89	1.91	2.775 (6)	162
N1—H1B···O3	0.89	2.03	2.916 (6)	177
N1—H1C···O5ⁱⁱ	0.89	1.96	2.837 (6)	168
O5—H5···O3	0.82	1.91	2.723 (6)	168
C13—H13C···O2ⁱⁱⁱ	0.96	2.58	3.491 (8)	158
C20—H20B···O2^iv	0.96	2.57	3.449 (8)	153

Symmetry codes: (i) −x, y+1/2, −z+1/2; (ii) −x, y−1/2, −z+1/2; (iii) x, y+1, z; (iv) −x+1, y+1/2, −z+1/2.

Acknowledgements

This work was supported by Shandong Provincial Natural Science Foundation, China (ZR2009BL027).

References

Bruker (1997). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Li, J. (2011). Acta Cryst. E67, o200. Web of Science CrossRef IUCr Journals Google Scholar
Liang, Z.-P. (2008). Acta Cryst. E64, o2416. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 67| Part 4| April 2011| Page o869

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

2-Methyl­propan-2-aminium 3,4,5,6-tetra­bromo-2-(meth­­oxy­carbon­yl)benzoate methanol monosolvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2-Methylpropan-2-aminium 3,4,5,6-tetrabromo-2-(methoxycarbonyl)benzoate methanol monosolvate