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

In the title compound, C(2)H(8)NO(+)·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].

Related literature

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

Experimental

Crystal data

C2H8NO+·C9H3Br4O4 −·CH4O

M = 588.89

Monoclinic,

a = 9.4231 (11) Å

b = 25.475 (2) Å

c = 8.3463 (7) Å

β = 111.990 (1)°

V = 1857.8 (3) Å3

Z = 4

Mo Kα radiation

μ = 8.69 mm−1

T = 298 K

0.42 × 0.35 × 0.34 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1997 ▶) T min = 0.121, T max = 0.156

9367 measured reflections

3269 independent reflections

1581 reflections with I > 2σ(I)

R int = 0.086

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.071

S = 1.00

3269 reflections

212 parameters

H-atom parameters constrained

Δρmax = 0.55 e Å−3

Δρmin = −0.58 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/S160053681100852X/kj2169sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681100852X/kj2169Isup2.hkl

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

C2H8NO+·C9H3Br4O4−·CH4O	F(000) = 1128
Mr = 588.89	Dx = 2.105 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.4231 (11) Å	Cell parameters from 1705 reflections
b = 25.475 (2) Å	θ = 2.9–21.8°
c = 8.3463 (7) Å	µ = 8.69 mm−1
β = 111.990 (1)°	T = 298 K
V = 1857.8 (3) Å3	Block, colorless
Z = 4	0.42 × 0.35 × 0.34 mm

Bruker SMART CCD diffractometer	3269 independent reflections
Radiation source: fine-focus sealed tube	1581 reflections with I > 2σ(I)
graphite	Rint = 0.086
φ and ω scans	θmax = 25.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −10→11
Tmin = 0.121, Tmax = 0.156	k = −30→28
9367 measured reflections	l = −9→9

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044	H-atom parameters constrained
wR(F2) = 0.071	w = 1/[σ2(Fo2) + (0.0103P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max = 0.001
3269 reflections	Δρmax = 0.55 e Å−3
212 parameters	Δρmin = −0.58 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00077 (5)

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	0.33226 (9)	0.40176 (3)	0.76997 (13)	0.0614 (3)
Br2	0.40915 (10)	0.52775 (3)	0.75108 (12)	0.0620 (3)
Br3	0.73518 (10)	0.56240 (3)	0.72387 (12)	0.0632 (3)
Br4	0.98636 (10)	0.47177 (3)	0.73227 (13)	0.0709 (3)
N1	0.4471 (6)	0.6959 (2)	0.6870 (8)	0.0456 (18)
H1A	0.4218	0.7297	0.6773	0.068*
H1B	0.3755	0.6775	0.7077	0.068*
H1C	0.4542	0.6848	0.5892	0.068*
O1	0.8414 (6)	0.3298 (2)	0.6314 (8)	0.0643 (18)
O2	1.0002 (7)	0.3545 (2)	0.8847 (9)	0.092 (2)
O3	0.6507 (6)	0.30316 (19)	0.8975 (8)	0.0702 (18)
O4	0.5049 (6)	0.30677 (18)	0.6230 (8)	0.0567 (17)
O5	0.7644 (6)	0.6848 (2)	0.6739 (8)	0.081 (2)
H5	0.6920	0.6850	0.5807	0.097*
O6	0.2414 (7)	0.6457 (2)	0.7949 (8)	0.095 (2)
H6	0.2570	0.6592	0.8891	0.114*
C1	0.8828 (10)	0.3586 (3)	0.7696 (14)	0.051 (2)
C2	0.5883 (10)	0.3264 (3)	0.7595 (14)	0.044 (2)
C3	0.7674 (8)	0.4002 (2)	0.7569 (9)	0.0337 (19)
C4	0.6248 (8)	0.3843 (3)	0.7589 (9)	0.0342 (19)
C5	0.5202 (7)	0.4236 (3)	0.7578 (9)	0.038 (2)
C6	0.5502 (8)	0.4761 (2)	0.7492 (9)	0.037 (2)
C7	0.6908 (9)	0.4915 (2)	0.7421 (10)	0.041 (2)
C8	0.7971 (8)	0.4530 (2)	0.7450 (10)	0.038 (2)
C9	0.9453 (9)	0.2862 (3)	0.6319 (12)	0.096 (3)
H9A	1.0227	0.2988	0.5928	0.145*
H9B	0.8878	0.2588	0.5563	0.145*
H9C	0.9927	0.2726	0.7471	0.145*
C10	0.5970 (9)	0.6887 (3)	0.8323 (10)	0.052 (2)
H10A	0.5915	0.7038	0.9365	0.062*
H10B	0.6174	0.6514	0.8525	0.062*
C11	0.7246 (9)	0.7134 (3)	0.7971 (11)	0.061 (3)
H11A	0.6954	0.7488	0.7547	0.074*
H11B	0.8133	0.7158	0.9040	0.074*
C12	0.1062 (10)	0.6179 (3)	0.7424 (12)	0.087 (3)
H12A	0.1093	0.5932	0.8306	0.130*
H12B	0.0927	0.5994	0.6375	0.130*
H12C	0.0224	0.6417	0.7225	0.130*

	U11	U22	U33	U12	U13	U23
Br1	0.0395 (5)	0.0646 (5)	0.0851 (8)	−0.0002 (5)	0.0292 (5)	0.0080 (6)
Br2	0.0537 (6)	0.0497 (5)	0.0860 (8)	0.0231 (5)	0.0299 (6)	0.0052 (5)
Br3	0.0653 (6)	0.0307 (4)	0.0958 (9)	−0.0021 (5)	0.0328 (6)	0.0015 (5)
Br4	0.0410 (6)	0.0579 (5)	0.1211 (10)	−0.0072 (5)	0.0387 (6)	−0.0055 (6)
N1	0.050 (5)	0.036 (3)	0.052 (5)	−0.013 (3)	0.020 (4)	−0.010 (4)
O1	0.044 (4)	0.061 (4)	0.078 (5)	0.021 (3)	0.012 (4)	−0.019 (4)
O2	0.060 (5)	0.086 (4)	0.092 (6)	0.041 (4)	−0.016 (4)	−0.030 (5)
O3	0.097 (5)	0.041 (3)	0.050 (5)	−0.003 (3)	0.001 (4)	0.011 (3)
O4	0.062 (4)	0.048 (3)	0.053 (5)	−0.022 (3)	0.014 (4)	−0.006 (3)
O5	0.049 (4)	0.097 (5)	0.093 (6)	0.017 (4)	0.023 (4)	0.017 (4)
O6	0.082 (5)	0.139 (5)	0.076 (5)	−0.057 (5)	0.042 (4)	−0.023 (4)
C1	0.037 (6)	0.037 (5)	0.064 (8)	−0.002 (5)	0.002 (6)	−0.010 (5)
C2	0.035 (6)	0.030 (5)	0.066 (8)	−0.003 (4)	0.018 (6)	−0.004 (5)
C3	0.021 (4)	0.031 (4)	0.046 (6)	0.008 (4)	0.008 (4)	−0.001 (4)
C4	0.031 (5)	0.035 (4)	0.031 (6)	0.006 (4)	0.004 (4)	0.003 (4)
C5	0.027 (5)	0.045 (4)	0.042 (6)	−0.005 (4)	0.012 (4)	0.001 (4)
C6	0.038 (5)	0.025 (4)	0.048 (6)	0.004 (4)	0.014 (4)	−0.002 (4)
C7	0.044 (5)	0.025 (4)	0.053 (6)	0.006 (4)	0.019 (5)	0.010 (4)
C8	0.025 (5)	0.038 (4)	0.044 (6)	−0.001 (4)	0.005 (4)	−0.002 (4)
C9	0.078 (7)	0.082 (7)	0.114 (9)	0.044 (6)	0.019 (7)	−0.041 (6)
C10	0.067 (7)	0.033 (4)	0.052 (7)	0.010 (5)	0.019 (6)	0.005 (5)
C11	0.039 (6)	0.066 (6)	0.070 (8)	0.006 (5)	0.010 (5)	0.004 (5)
C12	0.067 (7)	0.092 (7)	0.113 (10)	−0.023 (6)	0.047 (7)	−0.027 (7)

Br1—C5	1.894 (6)	C2—C4	1.514 (9)
Br2—C6	1.875 (6)	C3—C8	1.384 (8)
Br3—C7	1.872 (6)	C3—C4	1.410 (8)
Br4—C8	1.888 (6)	C4—C5	1.402 (8)
N1—C10	1.489 (8)	C5—C6	1.376 (8)
N1—H1A	0.8900	C6—C7	1.404 (8)
N1—H1B	0.8900	C7—C8	1.397 (8)
N1—H1C	0.8900	C9—H9A	0.9600
O1—C1	1.298 (9)	C9—H9B	0.9600
O1—C9	1.480 (7)	C9—H9C	0.9600
O2—C1	1.166 (9)	C10—C11	1.481 (8)
O3—C2	1.232 (9)	C10—H10A	0.9700
O4—C2	1.223 (9)	C10—H10B	0.9700
O5—C11	1.420 (8)	C11—H11A	0.9700
O5—H5	0.8200	C11—H11B	0.9700
O6—C12	1.377 (8)	C12—H12A	0.9600
O6—H6	0.8200	C12—H12B	0.9600
C1—C3	1.493 (9)	C12—H12C	0.9600
C10—N1—H1A	109.5	C6—C7—Br3	121.1 (5)
C10—N1—H1B	109.5	C3—C8—C7	121.5 (6)
H1A—N1—H1B	109.5	C3—C8—Br4	118.1 (5)
C10—N1—H1C	109.5	C7—C8—Br4	120.5 (5)
H1A—N1—H1C	109.5	O1—C9—H9A	109.5
H1B—N1—H1C	109.5	O1—C9—H9B	109.5
C1—O1—C9	116.4 (6)	H9A—C9—H9B	109.5
C11—O5—H5	109.5	O1—C9—H9C	109.5
C12—O6—H6	109.5	H9A—C9—H9C	109.5
O2—C1—O1	123.9 (8)	H9B—C9—H9C	109.5
O2—C1—C3	124.3 (9)	C11—C10—N1	112.3 (6)
O1—C1—C3	111.7 (8)	C11—C10—H10A	109.2
O4—C2—O3	126.1 (7)	N1—C10—H10A	109.2
O4—C2—C4	117.6 (9)	C11—C10—H10B	109.2
O3—C2—C4	116.2 (8)	N1—C10—H10B	109.2
C8—C3—C4	119.9 (6)	H10A—C10—H10B	107.9
C8—C3—C1	122.2 (6)	O5—C11—C10	112.3 (6)
C4—C3—C1	117.9 (6)	O5—C11—H11A	109.1
C5—C4—C3	117.8 (6)	C10—C11—H11A	109.1
C5—C4—C2	122.3 (6)	O5—C11—H11B	109.1
C3—C4—C2	119.9 (6)	C10—C11—H11B	109.1
C6—C5—C4	122.4 (6)	H11A—C11—H11B	107.9
C6—C5—Br1	120.2 (5)	O6—C12—H12A	109.5
C4—C5—Br1	117.4 (5)	O6—C12—H12B	109.5
C5—C6—C7	119.4 (6)	H12A—C12—H12B	109.5
C5—C6—Br2	121.5 (5)	O6—C12—H12C	109.5
C7—C6—Br2	119.2 (5)	H12A—C12—H12C	109.5
C8—C7—C6	119.0 (5)	H12B—C12—H12C	109.5
C8—C7—Br3	119.9 (5)
C9—O1—C1—O2	6.2 (13)	C4—C5—C6—C7	−0.4 (11)
C9—O1—C1—C3	−178.2 (6)	Br1—C5—C6—C7	179.3 (5)
O2—C1—C3—C8	63.9 (13)	C4—C5—C6—Br2	−179.1 (5)
O1—C1—C3—C8	−111.7 (8)	Br1—C5—C6—Br2	0.5 (9)
O2—C1—C3—C4	−115.6 (10)	C5—C6—C7—C8	−0.4 (11)
O1—C1—C3—C4	68.9 (9)	Br2—C6—C7—C8	178.4 (6)
C8—C3—C4—C5	−3.3 (11)	C5—C6—C7—Br3	178.2 (6)
C1—C3—C4—C5	176.1 (7)	Br2—C6—C7—Br3	−3.0 (9)
C8—C3—C4—C2	175.8 (8)	C4—C3—C8—C7	2.7 (12)
C1—C3—C4—C2	−4.7 (11)	C1—C3—C8—C7	−176.7 (7)
O4—C2—C4—C5	77.2 (10)	C4—C3—C8—Br4	−177.1 (5)
O3—C2—C4—C5	−105.4 (9)	C1—C3—C8—Br4	3.4 (11)
O4—C2—C4—C3	−101.9 (9)	C6—C7—C8—C3	−0.8 (12)
O3—C2—C4—C3	75.5 (10)	Br3—C7—C8—C3	−179.5 (6)
C3—C4—C5—C6	2.2 (11)	C6—C7—C8—Br4	179.0 (5)
C2—C4—C5—C6	−176.9 (8)	Br3—C7—C8—Br4	0.4 (9)
C3—C4—C5—Br1	−177.5 (5)	N1—C10—C11—O5	−73.5 (8)
C2—C4—C5—Br1	3.4 (10)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O3i	0.89	2.01	2.885 (7)	168
N1—H1B···O6	0.89	1.86	2.740 (7)	168
N1—H1C···O4ii	0.89	1.96	2.789 (8)	154
O5—H5···O4ii	0.82	2.00	2.813 (8)	169
O6—H6···O3iii	0.82	1.92	2.714 (8)	163

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O3i	0.89	2.01	2.885 (7)	168
N1—H1B⋯O6	0.89	1.86	2.740 (7)	168
N1—H1C⋯O4ii	0.89	1.96	2.789 (8)	154
O5—H5⋯O4ii	0.82	2.00	2.813 (8)	169
O6—H6⋯O3iii	0.82	1.92	2.714 (8)	163

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