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

Li, J.

doi:10.1107/S1600536811008543

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 4| April 2011| Page o900

doi:10.1107/S1600536811008543

Open

access

2-Methylanilinium 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 13 February 2011; accepted 6 March 2011; online 15 March 2011)

In the anion of the title compound, C₇H₁₀N⁺·C₉H₃Br₄O₄⁻·CH₃O, the dihedral angles formed by the benzene ring and the mean planes of the carboxylate and methoxycarbonyl groups are 74.8 (5) and 75.0 (5)°, respectively. In the crystal, intermolecular N—H⋯O and O—H⋯O hydrogen bonds link the components into chains along [100]. Additional stabilization is provided by weak intermolecular C—H⋯O hydrogen bonds.

Related literature

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

Experimental

Crystal data

C₇H₁₀N⁺·C₉H₃Br₄O₄⁻·CH₄O
M_r = 634.96
Monoclinic, P 2₁ /c
a = 8.1909 (8) Å
b = 13.5551 (12) Å
c = 19.5082 (16) Å
β = 90.371 (1)°
V = 2165.9 (3) Å³
Z = 4
Mo Kα radiation
μ = 7.46 mm⁻¹
T = 298 K
0.40 × 0.32 × 0.28 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1997 ) T_min = 0.154, T_max = 0.229
10672 measured reflections
3811 independent reflections
2507 reflections with I > 2σ(I)
R_int = 0.055

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.072
S = 1.07
3811 reflections
248 parameters
H-atom parameters constrained
Δρ_max = 0.71 e Å⁻³
Δρ_min = −0.59 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O5ⁱ	0.89	1.87	2.756 (6)	178
N1—H1B⋯O4ⁱ	0.89	1.87	2.746 (5)	170
O5—H5⋯O3ⁱⁱ	0.82	1.83	2.645 (5)	173
C15—H15⋯O5ⁱ	0.93	2.55	3.281 (7)	135
C17—H17B⋯O2	0.96	2.47	3.296 (9)	144
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) x+1, y, z.

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/S1600536811008543/lh5212sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811008543/lh5212Isup2.hkl

checkCIF report

Comment top

4,5,6,7-Tetrabromo-2-ethylisoindoline-1,3-dione is an important flame retardant. 3,4,5,6-tetrabromo-2-(Methoxycarbonyl)benzoic acid is an intermediate in the sytnthesis of this flame retardant. In this paper, the structure of the title compound is reported. The asymmetric unit of the title compound (I) contains one o-toluidinium cation, one 3,4,5,6-tetrabromo-2-(methoxycarbonyl)benzoate anion and one methanol solvent molecule (Fig. 1). In the anion, the dihedral angles formed by the benzene ring and the mean-planes of the carboxylate and methoxycarbonyl groups are 74.8 (5) and 75.0 (5) °, respectively. The bond lengths and angles are in agreement with those which are related in ethylammonium 2-(methoxycarbonyl)-3,4,5,6-tetrabromobenzoate methanol solvate (Li, 2011) and in ethane-1,2-diammonium bis(2-(methoxycarbonyl)-3,4,5,6-tetrabromobenzoate) methanol solvate (Liang, 2008). In the crystal, intermolecular N—H···O and O—H···O hydrogen bonds link the components of the structure into one-dimensional chains along [100] (Fig. 2). Additional stabilization is provided by weak intermolecular C-H···O hydrogen bonds.

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 and then o-toluidine (1.07 g, 0.01 mol) was added to the above solution. The solution was mixed 20 min at room temperature. This 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 (I), drawn with 30% probability ellipsoids.
	Fig. 2. Part of the crystal structure of (I) with hydrogen bonds shown as dashed lines.

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

Crystal data top

C₇H₁₀N⁺·C₉H₃Br₄O₄⁻·CH₄O	F(000) = 1224
M_r = 634.96	D_x = 1.947 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2873 reflections
a = 8.1909 (8) Å	θ = 2.6–23.9°
b = 13.5551 (12) Å	µ = 7.46 mm⁻¹
c = 19.5082 (16) Å	T = 298 K
β = 90.371 (1)°	Block, colorless
V = 2165.9 (3) Å³	0.40 × 0.32 × 0.28 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	3811 independent reflections
Radiation source: fine-focus sealed tube	2507 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.055
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −9→9
T_min = 0.154, T_max = 0.229	k = −13→16
10672 measured reflections	l = −23→21

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.072	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0232P)²] where P = (F_o² + 2F_c²)/3
3811 reflections	(Δ/σ)_max < 0.001
248 parameters	Δρ_max = 0.71 e Å⁻³
0 restraints	Δρ_min = −0.59 e Å⁻³

Crystal data top

C₇H₁₀N⁺·C₉H₃Br₄O₄⁻·CH₄O	V = 2165.9 (3) Å³
M_r = 634.96	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.1909 (8) Å	µ = 7.46 mm⁻¹
b = 13.5551 (12) Å	T = 298 K
c = 19.5082 (16) Å	0.40 × 0.32 × 0.28 mm
β = 90.371 (1)°

Data collection top

Bruker SMART CCD diffractometer	3811 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1997)	2507 reflections with I > 2σ(I)
T_min = 0.154, T_max = 0.229	R_int = 0.055
10672 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.072	H-atom parameters constrained
S = 1.07	Δρ_max = 0.71 e Å⁻³
3811 reflections	Δρ_min = −0.59 e Å⁻³
248 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	0.03655 (7)	0.49170 (4)	0.40325 (2)	0.03923 (16)
Br2	0.02019 (8)	0.40894 (4)	0.24560 (2)	0.05302 (19)
Br3	0.15610 (7)	0.18668 (4)	0.20996 (2)	0.05158 (18)
Br4	0.29944 (7)	0.04678 (4)	0.33723 (3)	0.05207 (19)
N1	0.3657 (5)	0.8858 (3)	0.05060 (18)	0.0390 (11)
H1A	0.3027	0.8481	0.0241	0.058*
H1B	0.4659	0.8882	0.0333	0.058*
H1C	0.3243	0.9464	0.0524	0.058*
O1	0.1935 (5)	0.0866 (3)	0.49814 (18)	0.0577 (11)
O2	0.4329 (5)	0.1646 (3)	0.5033 (2)	0.0712 (13)
O3	0.1279 (4)	0.3275 (2)	0.55173 (15)	0.0374 (9)
O4	0.3365 (4)	0.4141 (2)	0.51013 (15)	0.0386 (9)
O5	0.8267 (5)	0.2644 (3)	0.5294 (2)	0.0714 (12)
H5	0.9166	0.2887	0.5373	0.107*
C1	0.3034 (8)	0.1514 (4)	0.4786 (2)	0.0398 (14)
C2	0.2195 (6)	0.3546 (3)	0.5050 (2)	0.0268 (11)
C3	0.2381 (5)	0.2138 (3)	0.4200 (2)	0.0265 (11)
C4	0.1913 (5)	0.3107 (3)	0.4340 (2)	0.0242 (11)
C5	0.1213 (6)	0.3663 (3)	0.3820 (2)	0.0293 (12)
C6	0.1100 (6)	0.3289 (3)	0.3151 (2)	0.0297 (12)
C7	0.1649 (6)	0.2341 (4)	0.3009 (2)	0.0315 (12)
C8	0.2249 (6)	0.1765 (3)	0.3535 (2)	0.0326 (12)
C9	0.2418 (9)	0.0245 (5)	0.5563 (3)	0.104 (3)
H9A	0.3277	−0.0193	0.5425	0.156*
H9B	0.1496	−0.0134	0.5712	0.156*
H9C	0.2798	0.0654	0.5932	0.156*
C10	0.3726 (6)	0.8439 (4)	0.1201 (3)	0.0410 (14)
C11	0.4507 (7)	0.8936 (4)	0.1712 (3)	0.0450 (15)
C12	0.4626 (8)	0.8472 (5)	0.2352 (3)	0.0645 (19)
H12	0.5158	0.8790	0.2712	0.077*
C13	0.3973 (9)	0.7565 (6)	0.2453 (3)	0.078 (2)
H13	0.4090	0.7263	0.2878	0.094*
C14	0.3140 (9)	0.7084 (5)	0.1937 (4)	0.080 (2)
H14	0.2653	0.6475	0.2017	0.096*
C15	0.3040 (7)	0.7521 (4)	0.1297 (3)	0.0584 (17)
H15	0.2517	0.7199	0.0936	0.070*
C16	0.5220 (7)	0.9958 (4)	0.1608 (3)	0.0619 (17)
H16A	0.5957	0.9947	0.1227	0.093*
H16B	0.5799	1.0156	0.2015	0.093*
H16C	0.4354	1.0418	0.1516	0.093*
C17	0.7840 (9)	0.2058 (7)	0.5817 (4)	0.159 (5)
H17A	0.8389	0.1435	0.5776	0.238*
H17B	0.6681	0.1954	0.5806	0.238*
H17C	0.8145	0.2365	0.6242	0.238*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0555 (4)	0.0286 (3)	0.0336 (3)	0.0129 (3)	0.0007 (2)	−0.0035 (2)
Br2	0.0803 (5)	0.0476 (4)	0.0309 (3)	0.0160 (3)	−0.0143 (3)	0.0012 (3)
Br3	0.0688 (4)	0.0524 (4)	0.0334 (3)	0.0099 (3)	−0.0113 (3)	−0.0209 (3)
Br4	0.0709 (5)	0.0284 (3)	0.0568 (4)	0.0109 (3)	−0.0097 (3)	−0.0151 (3)
N1	0.037 (3)	0.034 (3)	0.046 (3)	0.006 (2)	0.002 (2)	0.004 (2)
O1	0.076 (3)	0.041 (2)	0.056 (2)	−0.002 (2)	0.000 (2)	0.023 (2)
O2	0.066 (3)	0.076 (3)	0.071 (3)	0.000 (3)	−0.030 (2)	0.010 (2)
O3	0.046 (2)	0.037 (2)	0.0284 (18)	−0.0014 (17)	0.0035 (17)	0.0013 (16)
O4	0.042 (2)	0.038 (2)	0.0355 (19)	−0.0106 (19)	0.0016 (16)	−0.0121 (16)
O5	0.055 (3)	0.071 (3)	0.088 (3)	−0.016 (2)	−0.018 (2)	0.027 (3)
C1	0.053 (4)	0.030 (3)	0.036 (3)	0.004 (3)	−0.009 (3)	−0.009 (3)
C2	0.031 (3)	0.023 (3)	0.026 (3)	0.007 (3)	−0.004 (2)	−0.003 (2)
C3	0.029 (3)	0.022 (3)	0.029 (3)	−0.002 (2)	−0.005 (2)	−0.003 (2)
C4	0.023 (3)	0.026 (3)	0.023 (2)	−0.007 (2)	0.003 (2)	0.000 (2)
C5	0.029 (3)	0.029 (3)	0.029 (3)	−0.003 (2)	0.005 (2)	−0.001 (2)
C6	0.034 (3)	0.034 (3)	0.021 (2)	0.000 (2)	−0.003 (2)	0.000 (2)
C7	0.038 (3)	0.034 (3)	0.022 (2)	−0.004 (3)	−0.005 (2)	−0.013 (2)
C8	0.035 (3)	0.023 (3)	0.039 (3)	−0.003 (2)	−0.003 (2)	−0.005 (2)
C9	0.150 (8)	0.073 (5)	0.088 (5)	0.021 (5)	0.012 (5)	0.053 (4)
C10	0.036 (3)	0.044 (4)	0.043 (3)	0.015 (3)	0.012 (3)	0.009 (3)
C11	0.041 (4)	0.052 (4)	0.042 (3)	0.024 (3)	0.005 (3)	0.001 (3)
C12	0.081 (5)	0.066 (5)	0.047 (4)	0.033 (4)	0.008 (3)	0.000 (3)
C13	0.104 (6)	0.077 (6)	0.054 (4)	0.035 (5)	0.016 (4)	0.019 (4)
C14	0.085 (6)	0.055 (5)	0.100 (6)	0.006 (4)	0.031 (5)	0.031 (4)
C15	0.066 (5)	0.050 (4)	0.060 (4)	0.002 (3)	0.011 (3)	0.009 (3)
C16	0.061 (4)	0.065 (4)	0.060 (4)	0.010 (3)	−0.006 (3)	−0.011 (3)
C17	0.097 (7)	0.290 (13)	0.089 (6)	−0.103 (8)	−0.040 (5)	0.090 (7)

Geometric parameters (Å, º) top

Br1—C5	1.883 (5)	C7—C8	1.376 (6)
Br2—C6	1.883 (4)	C9—H9A	0.9600
Br3—C7	1.889 (4)	C9—H9B	0.9600
Br4—C8	1.889 (5)	C9—H9C	0.9600
N1—C10	1.471 (6)	C10—C11	1.359 (7)
N1—H1A	0.8900	C10—C15	1.379 (7)
N1—H1B	0.8900	C11—C12	1.402 (7)
N1—H1C	0.8900	C11—C16	1.518 (7)
O1—C1	1.315 (6)	C12—C13	1.356 (8)
O1—C9	1.464 (6)	C12—H12	0.9300
O2—C1	1.176 (6)	C13—C14	1.377 (9)
O3—C2	1.239 (5)	C13—H13	0.9300
O4—C2	1.256 (5)	C14—C15	1.383 (8)
O5—C17	1.341 (7)	C14—H14	0.9300
O5—H5	0.8200	C15—H15	0.9300
C1—C3	1.517 (6)	C16—H16A	0.9600
C2—C4	1.525 (6)	C16—H16B	0.9600
C3—C4	1.395 (6)	C16—H16C	0.9600
C3—C8	1.397 (6)	C17—H17A	0.9600
C4—C5	1.385 (6)	C17—H17B	0.9600
C5—C6	1.403 (6)	C17—H17C	0.9600
C6—C7	1.390 (6)

C10—N1—H1A	109.5	H9A—C9—H9B	109.5
C10—N1—H1B	109.5	O1—C9—H9C	109.5
H1A—N1—H1B	109.5	H9A—C9—H9C	109.5
C10—N1—H1C	109.5	H9B—C9—H9C	109.5
H1A—N1—H1C	109.5	C11—C10—C15	122.6 (5)
H1B—N1—H1C	109.5	C11—C10—N1	120.0 (5)
C1—O1—C9	115.2 (5)	C15—C10—N1	117.4 (5)
C17—O5—H5	109.5	C10—C11—C12	117.4 (5)
O2—C1—O1	126.9 (5)	C10—C11—C16	122.3 (5)
O2—C1—C3	122.4 (5)	C12—C11—C16	120.3 (6)
O1—C1—C3	110.6 (5)	C13—C12—C11	120.7 (6)
O3—C2—O4	126.6 (4)	C13—C12—H12	119.7
O3—C2—C4	117.7 (4)	C11—C12—H12	119.7
O4—C2—C4	115.7 (4)	C12—C13—C14	121.2 (6)
C4—C3—C8	120.1 (4)	C12—C13—H13	119.4
C4—C3—C1	118.3 (4)	C14—C13—H13	119.4
C8—C3—C1	121.6 (4)	C13—C14—C15	118.9 (6)
C5—C4—C3	118.9 (4)	C13—C14—H14	120.6
C5—C4—C2	120.8 (4)	C15—C14—H14	120.6
C3—C4—C2	120.3 (4)	C10—C15—C14	119.2 (6)
C4—C5—C6	120.6 (4)	C10—C15—H15	120.4
C4—C5—Br1	118.8 (3)	C14—C15—H15	120.4
C6—C5—Br1	120.6 (3)	C11—C16—H16A	109.5
C7—C6—C5	120.0 (4)	C11—C16—H16B	109.5
C7—C6—Br2	121.0 (3)	H16A—C16—H16B	109.5
C5—C6—Br2	119.0 (3)	C11—C16—H16C	109.5
C8—C7—C6	119.4 (4)	H16A—C16—H16C	109.5
C8—C7—Br3	121.2 (4)	H16B—C16—H16C	109.5
C6—C7—Br3	119.4 (3)	O5—C17—H17A	109.5
C7—C8—C3	120.8 (4)	O5—C17—H17B	109.5
C7—C8—Br4	121.1 (3)	H17A—C17—H17B	109.5
C3—C8—Br4	118.0 (3)	O5—C17—H17C	109.5
O1—C9—H9A	109.5	H17A—C17—H17C	109.5
O1—C9—H9B	109.5	H17B—C17—H17C	109.5

C9—O1—C1—O2	−0.9 (8)	Br2—C6—C7—C8	−177.9 (4)
C9—O1—C1—C3	−178.0 (4)	C5—C6—C7—Br3	−177.7 (3)
O2—C1—C3—C4	−72.0 (7)	Br2—C6—C7—Br3	2.2 (6)
O1—C1—C3—C4	105.2 (5)	C6—C7—C8—C3	−2.9 (7)
O2—C1—C3—C8	107.7 (6)	Br3—C7—C8—C3	177.0 (3)
O1—C1—C3—C8	−75.1 (6)	C6—C7—C8—Br4	179.5 (3)
C8—C3—C4—C5	4.5 (7)	Br3—C7—C8—Br4	−0.6 (6)
C1—C3—C4—C5	−175.7 (4)	C4—C3—C8—C7	−0.5 (7)
C8—C3—C4—C2	−174.5 (4)	C1—C3—C8—C7	179.8 (5)
C1—C3—C4—C2	5.2 (7)	C4—C3—C8—Br4	177.2 (3)
O3—C2—C4—C5	106.2 (5)	C1—C3—C8—Br4	−2.5 (6)
O4—C2—C4—C5	−74.8 (6)	C15—C10—C11—C12	1.1 (8)
O3—C2—C4—C3	−74.8 (6)	N1—C10—C11—C12	−176.0 (4)
O4—C2—C4—C3	104.2 (5)	C15—C10—C11—C16	−178.3 (5)
C3—C4—C5—C6	−5.2 (7)	N1—C10—C11—C16	4.6 (8)
C2—C4—C5—C6	173.8 (4)	C10—C11—C12—C13	−0.4 (8)
C3—C4—C5—Br1	173.1 (3)	C16—C11—C12—C13	179.1 (6)
C2—C4—C5—Br1	−7.8 (6)	C11—C12—C13—C14	−1.7 (10)
C4—C5—C6—C7	1.9 (7)	C12—C13—C14—C15	3.0 (10)
Br1—C5—C6—C7	−176.4 (3)	C11—C10—C15—C14	0.2 (8)
C4—C5—C6—Br2	−178.0 (3)	N1—C10—C15—C14	177.4 (5)
Br1—C5—C6—Br2	3.7 (5)	C13—C14—C15—C10	−2.2 (9)
C5—C6—C7—C8	2.2 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O5ⁱ	0.89	1.87	2.756 (6)	178
N1—H1B···O4ⁱ	0.89	1.87	2.746 (5)	170
O5—H5···O3ⁱⁱ	0.82	1.83	2.645 (5)	173
C15—H15···O5ⁱ	0.93	2.55	3.281 (7)	135
C17—H17B···O2	0.96	2.47	3.296 (9)	144

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

Experimental details

Crystal data
Chemical formula	C₇H₁₀N⁺·C₉H₃Br₄O₄⁻·CH₄O
M_r	634.96
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	8.1909 (8), 13.5551 (12), 19.5082 (16)
β (°)	90.371 (1)
V (Å³)	2165.9 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	7.46
Crystal size (mm)	0.40 × 0.32 × 0.28

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1997)
T_min, T_max	0.154, 0.229
No. of measured, independent and observed [I > 2σ(I)] reflections	10672, 3811, 2507
R_int	0.055
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.072, 1.07
No. of reflections	3811
No. of parameters	248
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.71, −0.59

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···O5ⁱ	0.89	1.87	2.756 (6)	178
N1—H1B···O4ⁱ	0.89	1.87	2.746 (5)	170
O5—H5···O3ⁱⁱ	0.82	1.83	2.645 (5)	173
C15—H15···O5ⁱ	0.93	2.55	3.281 (7)	135
C17—H17B···O2	0.96	2.47	3.296 (9)	144

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

Acknowledgements

The author thanks Shandong Provincial Natural Science Foundation, China (ZR2009BL027) for support.

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

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 4| April 2011| Page o900

doi:10.1107/S1600536811008543

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

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