2-Methyl-propan-2-aminium 3,4,5,6-tetra-bromo-2-(meth-oxy-carbon-yl)benzoate methanol monosolvate.

In the crystal structure of the title compound, C(4)H(12)N(+)·C(9)H(3)Br(4)O(4) (-)·CH(4)O, inter-molecular 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 = 600.94

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.072

S = 1.06

3597 reflections

217 parameters

H-atom parameters constrained

Δρmax = 0.45 e Å−3

Δρmin = −0.52 e Å−3

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.

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C4H12N+·C9H3Br4O4−·CH4O	F(000) = 1160
Mr = 600.94	Dx = 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

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

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(Fo2) + (0.0138P)2] where P = (Fo2 + 2Fc2)/3
3597 reflections	(Δ/σ)max < 0.001
217 parameters	Δρmax = 0.45 e Å−3
0 restraints	Δρmin = −0.52 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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···O2iv	0.96	2.57	3.449 (8)	153

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⋯O2iv	0.96	2.57	3.449 (8)	153

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