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

In the crystal structure of the title compound, C(2)H(8)N(+)·C(9)H(3)Br(4)O(4) (-)·CH(4)O, inter-molecular N-H⋯O and O-H⋯O hydrogen bonds link the components into chains along [001]. Additional stabilization is supplied by weak C-H⋯O and C-H⋯Br inter-actions.

Related literature

For a related structure, see: Liang (2008 ▶).

Experimental

Crystal data

C2H8N+·C9H3Br4O4 −·CH4O

M = 572.89

Monoclinic,

a = 9.4651 (8) Å

b = 25.6544 (19) Å

c = 8.3365 (6) Å

β = 112.787 (1)°

V = 1866.3 (2) Å3

Z = 4

Mo Kα radiation

μ = 8.64 mm−1

T = 298 K

0.40 × 0.35 × 0.33 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1997 ▶) T min = 0.130, T max = 0.163

9436 measured reflections

3295 independent reflections

1454 reflections with I > 2σ(I)

R int = 0.086

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.068

S = 0.99

3295 reflections

200 parameters

H-atom parameters constrained

Δρmax = 0.49 e Å−3

Δρmin = −0.51 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/S1600536810052591/lh5189sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810052591/lh5189Isup2.hkl

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

C2H8N+·C9H3Br4O4−·CH4O	F(000) = 1096
Mr = 572.89	Dx = 2.039 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1513 reflections
a = 9.4651 (8) Å	θ = 2.3–20.6°
b = 25.6544 (19) Å	µ = 8.64 mm−1
c = 8.3365 (6) Å	T = 298 K
β = 112.787 (1)°	Block, colorless
V = 1866.3 (2) Å3	0.40 × 0.35 × 0.33 mm
Z = 4

Bruker SMART CCD diffractometer	3295 independent reflections
Radiation source: fine-focus sealed tube	1454 reflections with I > 2σ(I)
graphite	Rint = 0.086
φ and ω scans	θmax = 25.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −9→11
Tmin = 0.130, Tmax = 0.163	k = −30→30
9436 measured reflections	l = −9→8

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.068	H-atom parameters constrained
S = 0.99	w = 1/[σ2(Fo2) + (0.0024P)2] where P = (Fo2 + 2Fc2)/3
3295 reflections	(Δ/σ)max = 0.001
200 parameters	Δρmax = 0.49 e Å−3
0 restraints	Δρmin = −0.51 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	0.32729 (8)	0.90633 (3)	0.26426 (13)	0.0702 (3)
Br2	0.40752 (9)	1.03175 (3)	0.25156 (12)	0.0705 (3)
Br3	0.73585 (10)	1.06551 (3)	0.23297 (14)	0.0807 (3)
Br4	0.98266 (9)	0.97499 (3)	0.23443 (13)	0.0773 (3)
N1	0.5436 (6)	0.7996 (2)	0.8034 (8)	0.0546 (19)
H1A	0.5376	0.8133	0.8986	0.082*
H1B	0.6186	0.8151	0.7820	0.082*
H1C	0.5631	0.7656	0.8196	0.082*
O1	0.8313 (6)	0.8333 (2)	0.1273 (8)	0.0672 (18)
O2	0.9937 (7)	0.8565 (2)	0.3871 (9)	0.101 (3)
O3	0.6431 (6)	0.8063 (2)	0.3863 (8)	0.076 (2)
O4	0.4945 (6)	0.8125 (2)	0.1079 (8)	0.0713 (19)
O5	0.7663 (7)	0.8481 (2)	0.7090 (7)	0.104 (2)
H5	0.7413	0.8383	0.6081	0.157*
C1	0.8783 (9)	0.8620 (3)	0.2667 (14)	0.050 (3)
C2	0.5820 (10)	0.8306 (3)	0.2499 (14)	0.050 (3)
C3	0.7630 (7)	0.9042 (3)	0.2521 (9)	0.0369 (19)
C4	0.6200 (8)	0.8886 (3)	0.2517 (9)	0.040 (2)
C5	0.5158 (7)	0.9276 (3)	0.2534 (9)	0.040 (2)
C6	0.5515 (7)	0.9794 (3)	0.2527 (9)	0.047 (2)
C7	0.6915 (8)	0.9947 (3)	0.2450 (10)	0.045 (2)
C8	0.7960 (7)	0.9565 (3)	0.2469 (9)	0.040 (2)
C9	0.9329 (9)	0.7886 (3)	0.1323 (11)	0.097 (3)
H9A	1.0367	0.8006	0.1685	0.146*
H9B	0.9010	0.7734	0.0185	0.146*
H9C	0.9266	0.7629	0.2131	0.146*
C10	0.3935 (9)	0.8076 (3)	0.6508 (10)	0.056 (2)
H10A	0.3730	0.8447	0.6333	0.068*
H10B	0.4018	0.7937	0.5466	0.068*
C11	0.2643 (8)	0.7820 (3)	0.6773 (10)	0.081 (3)
H11A	0.2763	0.7449	0.6766	0.121*
H11B	0.1697	0.7919	0.5854	0.121*
H11C	0.2630	0.7926	0.7872	0.121*
C12	0.8988 (9)	0.8774 (3)	0.7572 (12)	0.104 (4)
H12A	0.9141	0.8959	0.8627	0.155*
H12B	0.8899	0.9019	0.6667	0.155*
H12C	0.9844	0.8548	0.7757	0.155*

	U11	U22	U33	U12	U13	U23
Br1	0.0399 (5)	0.0808 (7)	0.1016 (9)	−0.0038 (5)	0.0403 (6)	0.0061 (6)
Br2	0.0615 (6)	0.0617 (6)	0.0956 (8)	0.0286 (5)	0.0386 (6)	0.0063 (6)
Br3	0.0898 (7)	0.0337 (5)	0.1331 (10)	−0.0058 (5)	0.0592 (7)	−0.0010 (6)
Br4	0.0455 (6)	0.0699 (7)	0.1306 (10)	−0.0122 (5)	0.0496 (6)	−0.0070 (6)
N1	0.061 (5)	0.042 (4)	0.072 (6)	−0.011 (3)	0.039 (4)	0.000 (4)
O1	0.057 (4)	0.063 (4)	0.077 (5)	0.027 (3)	0.022 (4)	−0.014 (4)
O2	0.068 (4)	0.114 (6)	0.085 (6)	0.048 (4)	−0.011 (4)	−0.033 (4)
O3	0.101 (5)	0.044 (4)	0.070 (5)	−0.006 (3)	0.020 (4)	0.019 (4)
O4	0.094 (5)	0.062 (4)	0.062 (5)	−0.038 (3)	0.035 (4)	−0.021 (4)
O5	0.101 (5)	0.150 (6)	0.074 (6)	−0.064 (4)	0.048 (4)	−0.018 (4)
C1	0.036 (6)	0.042 (6)	0.072 (9)	0.003 (5)	0.020 (6)	−0.009 (6)
C2	0.047 (6)	0.036 (6)	0.075 (9)	−0.006 (5)	0.035 (6)	−0.005 (6)
C3	0.031 (4)	0.028 (4)	0.057 (6)	−0.003 (4)	0.023 (4)	−0.005 (5)
C4	0.043 (5)	0.032 (5)	0.043 (6)	0.007 (4)	0.017 (5)	−0.002 (4)
C5	0.026 (4)	0.038 (5)	0.060 (6)	−0.007 (4)	0.021 (4)	−0.004 (5)
C6	0.035 (5)	0.045 (6)	0.058 (6)	0.014 (4)	0.016 (5)	−0.001 (4)
C7	0.032 (5)	0.033 (5)	0.068 (6)	−0.003 (4)	0.019 (5)	0.003 (4)
C8	0.016 (4)	0.041 (5)	0.062 (6)	−0.001 (4)	0.014 (4)	−0.002 (5)
C9	0.090 (7)	0.080 (7)	0.106 (9)	0.045 (6)	0.022 (6)	−0.025 (6)
C10	0.077 (6)	0.046 (6)	0.040 (6)	0.018 (5)	0.015 (6)	0.009 (5)
C11	0.052 (6)	0.097 (7)	0.085 (8)	−0.013 (5)	0.017 (6)	0.016 (6)
C12	0.082 (7)	0.100 (8)	0.144 (10)	−0.050 (6)	0.060 (7)	−0.030 (7)

Br1—C5	1.902 (6)	C3—C4	1.411 (8)
Br2—C6	1.911 (6)	C4—C5	1.410 (8)
Br3—C7	1.876 (6)	C5—C6	1.370 (8)
Br4—C8	1.871 (6)	C6—C7	1.408 (7)
N1—C10	1.509 (8)	C7—C8	1.389 (8)
N1—H1A	0.8900	C9—H9A	0.9600
N1—H1B	0.8900	C9—H9B	0.9600
N1—H1C	0.8900	C9—H9C	0.9600
O1—C1	1.301 (9)	C10—C11	1.478 (8)
O1—C9	1.487 (7)	C10—H10A	0.9700
O2—C1	1.171 (9)	C10—H10B	0.9700
O3—C2	1.227 (9)	C11—H11A	0.9600
O4—C2	1.241 (9)	C11—H11B	0.9600
O5—C12	1.381 (7)	C11—H11C	0.9600
O5—H5	0.8200	C12—H12A	0.9600
C1—C3	1.507 (9)	C12—H12B	0.9600
C2—C4	1.530 (9)	C12—H12C	0.9600
C3—C8	1.381 (7)
C10—N1—H1A	109.5	C6—C7—Br3	120.5 (5)
C10—N1—H1B	109.5	C3—C8—C7	121.2 (6)
H1A—N1—H1B	109.5	C3—C8—Br4	118.6 (5)
C10—N1—H1C	109.5	C7—C8—Br4	120.2 (5)
H1A—N1—H1C	109.5	O1—C9—H9A	109.5
H1B—N1—H1C	109.5	O1—C9—H9B	109.5
C1—O1—C9	114.7 (6)	H9A—C9—H9B	109.5
C12—O5—H5	109.5	O1—C9—H9C	109.5
O2—C1—O1	125.5 (8)	H9A—C9—H9C	109.5
O2—C1—C3	124.2 (9)	H9B—C9—H9C	109.5
O1—C1—C3	110.4 (7)	C11—C10—N1	112.1 (6)
O3—C2—O4	126.6 (8)	C11—C10—H10A	109.2
O3—C2—C4	117.4 (8)	N1—C10—H10A	109.2
O4—C2—C4	116.0 (8)	C11—C10—H10B	109.2
C8—C3—C4	120.3 (6)	N1—C10—H10B	109.2
C8—C3—C1	122.3 (6)	H10A—C10—H10B	107.9
C4—C3—C1	117.4 (6)	C10—C11—H11A	109.5
C5—C4—C3	118.2 (6)	C10—C11—H11B	109.5
C5—C4—C2	121.9 (7)	H11A—C11—H11B	109.5
C3—C4—C2	119.9 (6)	C10—C11—H11C	109.5
C6—C5—C4	121.0 (6)	H11A—C11—H11C	109.5
C6—C5—Br1	121.0 (5)	H11B—C11—H11C	109.5
C4—C5—Br1	118.0 (5)	O5—C12—H12A	109.5
C5—C6—C7	120.6 (6)	O5—C12—H12B	109.5
C5—C6—Br2	120.3 (5)	H12A—C12—H12B	109.5
C7—C6—Br2	119.0 (6)	O5—C12—H12C	109.5
C8—C7—C6	118.8 (6)	H12A—C12—H12C	109.5
C8—C7—Br3	120.8 (5)	H12B—C12—H12C	109.5
C9—O1—C1—O2	3.5 (13)	C2—C4—C5—Br1	2.8 (10)
C9—O1—C1—C3	−176.8 (6)	C4—C5—C6—C7	1.9 (11)
O2—C1—C3—C8	64.3 (12)	Br1—C5—C6—C7	179.9 (5)
O1—C1—C3—C8	−115.3 (8)	C4—C5—C6—Br2	179.1 (5)
O2—C1—C3—C4	−112.9 (10)	Br1—C5—C6—Br2	−2.9 (9)
O1—C1—C3—C4	67.5 (9)	C5—C6—C7—C8	−3.2 (11)
C8—C3—C4—C5	−2.7 (10)	Br2—C6—C7—C8	179.6 (6)
C1—C3—C4—C5	174.6 (7)	C5—C6—C7—Br3	177.0 (6)
C8—C3—C4—C2	177.5 (7)	Br2—C6—C7—Br3	−0.2 (8)
C1—C3—C4—C2	−5.3 (11)	C4—C3—C8—C7	1.4 (11)
O3—C2—C4—C5	−104.5 (9)	C1—C3—C8—C7	−175.7 (8)
O4—C2—C4—C5	77.2 (10)	C4—C3—C8—Br4	−176.4 (5)
O3—C2—C4—C3	75.3 (10)	C1—C3—C8—Br4	6.4 (11)
O4—C2—C4—C3	−103.0 (8)	C6—C7—C8—C3	1.5 (11)
C3—C4—C5—C6	1.0 (10)	Br3—C7—C8—C3	−178.7 (5)
C2—C4—C5—C6	−179.1 (7)	C6—C7—C8—Br4	179.3 (5)
C3—C4—C5—Br1	−177.0 (5)	Br3—C7—C8—Br4	−0.9 (9)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O4i	0.89	1.94	2.772 (9)	155
N1—H1B···O5	0.89	1.92	2.810 (9)	174
N1—H1C···O3ii	0.89	1.99	2.871 (7)	170
N1—H1C···O4ii	0.89	2.58	3.249 (8)	132
O5—H5···O3	0.82	1.90	2.705 (8)	165
C10—H10A···Br3iii	0.97	2.92	3.736 (8)	143
C11—H11B···O2iv	0.96	2.47	3.357 (10)	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O4i	0.89	1.94	2.772 (9)	155
N1—H1B⋯O5	0.89	1.92	2.810 (9)	174
N1—H1C⋯O3ii	0.89	1.99	2.871 (7)	170
N1—H1C⋯O4ii	0.89	2.58	3.249 (8)	132
O5—H5⋯O3	0.82	1.90	2.705 (8)	165
C10—H10A⋯Br3iii	0.97	2.92	3.736 (8)	143
C11—H11B⋯O2iv	0.96	2.47	3.357 (10)	153

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