Propan-1-aminium 3,4,5,6-tetra­bromo-2-(meth­oxy­carbon­yl)benzoate N,N-dimethyl­formamide monosolvate

Li, J.

doi:10.1107/S1600536811016850

organic compounds

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Volume 67| Part 6| June 2011| Page o1356

doi:10.1107/S1600536811016850

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Propan-1-aminium 3,4,5,6-tetrabromo-2-(methoxycarbonyl)benzoate N,N-dimethylformamide 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 30 April 2011; accepted 4 May 2011; online 7 May 2011)

In the anion of the title solvated molecular salt, C₃H₁₀N⁺·C₉H₃Br₄O₄⁻·C₃H₇NO, the dihedral angles formed by the aromatic ring and the mean planes of the carboxylate and methoxycarbonyl groups are 64.3 (3) and 75.2 (3)°, respectively. The C atoms of the propan-1-aminium cation are disordered over two sets of sites in a 0.65 (3):0.35 (3) ratio. The crystal structure is stabilized by N—H⋯O hydrogen bonds.

Related literature

For related structures, see: Li (2011a ,b ).

Experimental

Crystal data

C₃H₁₀N⁺·C₉H₃Br₄O₄⁻·C₃H₇NO
M_r = 627.97
Monoclinic, P 2₁ /n
a = 11.8964 (11) Å
b = 10.5198 (10) Å
c = 17.3743 (17) Å
β = 93.188 (1)°
V = 2171.0 (4) Å³
Z = 4
Mo Kα radiation
μ = 7.44 mm⁻¹
T = 298 K
0.40 × 0.37 × 0.24 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1997 ) T_min = 0.155, T_max = 0.268
10672 measured reflections
3821 independent reflections
1836 reflections with I > 2σ(I)
R_int = 0.069

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.104
S = 1.03
3821 reflections
268 parameters
H-atom parameters constrained
Δρ_max = 0.57 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O3	0.89	1.87	2.757 (7)	175
N1—H1B⋯O4ⁱ	0.89	2.04	2.812 (8)	144
N1—H1C⋯O5ⁱⁱ	0.89	1.91	2.762 (8)	160
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) x, y-1, 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); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811016850/bt5538sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811016850/bt5538Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811016850/bt5538Isup3.cml

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 synthesis of this flame retardant. The asymmetric unit of the title compound contains one propan-1-aminium cation, one 3,4,5,6-tetrabromo-2-(methoxycarbonyl)benzoate anion and one N,N-dimethylformamide solvent molecule (Fig. 1). In the anion of the title compound, the dihedral angles formed by the benzene ring and the mean planes of the carboxylate and methoxycarbonyl groups are 64.3 (3) and 75.2 (3) °, respectively. The carbon atoms of the propan-1-aminium cation are disordered. 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, 2011a) and in 2-Methylanilinium 3,4,5,6-tetrabromo-2-(methoxycarbonyl)benzoate methanol monosolvate(Li, 2011b). The crystal structure is stabilized by N—H···O hydrogen bonds (see Fig. 2 and Table 1).

Related literature top

For related structures, see: Li (2011a,b).

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. Then propan-1-amine (0.59 g, 0.01 mol) was added to the above solution and mixed for 30 min at room temperature. After filtration, filter cake was disolved in N,N-dimethylformamide (10 ml), the solution was kept at room temperature for 15 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); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound drawn with 30% probability ellipsoids.
	Fig. 2. The crystal structure is stabilized by N—H···O hydrogen bonds

Propan-1-aminium 3,4,5,6-tetrabromo-2-(methoxycarbonyl)benzoate N,N-dimethylformamide monosolvate top

Crystal data top

C₃H₁₀N⁺·C₉H₃Br₄O₄⁻·C₃H₇NO	F(000) = 1216
M_r = 627.97	D_x = 1.921 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 11.8964 (11) Å	Cell parameters from 1875 reflections
b = 10.5198 (10) Å	θ = 2.3–20.1°
c = 17.3743 (17) Å	µ = 7.44 mm⁻¹
β = 93.188 (1)°	T = 298 K
V = 2171.0 (4) Å³	Block, colorless
Z = 4	0.40 × 0.37 × 0.24 mm

Data collection top

Bruker SMART CCD diffractometer	3821 independent reflections
Radiation source: fine-focus sealed tube	1836 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.069
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −14→14
T_min = 0.155, T_max = 0.268	k = −12→12
10672 measured reflections	l = −10→20

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.104	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0346P)²] where P = (F_o² + 2F_c²)/3
3821 reflections	(Δ/σ)_max = 0.001
268 parameters	Δρ_max = 0.57 e Å⁻³
0 restraints	Δρ_min = −0.38 e Å⁻³

Crystal data top

C₃H₁₀N⁺·C₉H₃Br₄O₄⁻·C₃H₇NO	V = 2171.0 (4) Å³
M_r = 627.97	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.8964 (11) Å	µ = 7.44 mm⁻¹
b = 10.5198 (10) Å	T = 298 K
c = 17.3743 (17) Å	0.40 × 0.37 × 0.24 mm
β = 93.188 (1)°

Data collection top

Bruker SMART CCD diffractometer	3821 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1997)	1836 reflections with I > 2σ(I)
T_min = 0.155, T_max = 0.268	R_int = 0.069
10672 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.104	H-atom parameters constrained
S = 1.03	Δρ_max = 0.57 e Å⁻³
3821 reflections	Δρ_min = −0.38 e Å⁻³
268 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	Occ. (<1)
Br1	0.54990 (6)	0.36358 (7)	0.43979 (5)	0.0768 (3)
Br2	0.77382 (6)	0.18088 (8)	0.44525 (5)	0.0787 (3)
Br3	0.82232 (6)	−0.00007 (9)	0.29589 (6)	0.0923 (3)
Br4	0.63517 (6)	−0.01203 (8)	0.14923 (5)	0.0828 (3)
N1	0.2391 (5)	0.0691 (6)	0.3225 (4)	0.0701 (18)
H1A	0.2650	0.1457	0.3109	0.105*	0.65 (3)
H1B	0.2129	0.0305	0.2796	0.105*	0.65 (3)
H1C	0.2947	0.0231	0.3447	0.105*	0.65 (3)
H1'A	0.1918	0.0366	0.2862	0.105*	0.35 (3)
H1'B	0.3018	0.0227	0.3261	0.105*	0.35 (3)
H1'C	0.2560	0.1487	0.3102	0.105*	0.35 (3)
N2	0.5289 (5)	0.8141 (7)	0.3665 (4)	0.0697 (18)
O1	0.3696 (4)	0.0717 (5)	0.1644 (3)	0.0631 (14)
O2	0.4289 (4)	0.2556 (5)	0.1162 (3)	0.0776 (16)
O3	0.3100 (3)	0.3064 (5)	0.2784 (3)	0.0721 (15)
O4	0.4291 (4)	0.4662 (5)	0.2792 (3)	0.0740 (16)
O5	0.4306 (5)	0.9836 (5)	0.4037 (3)	0.0917 (19)
C1	0.4351 (6)	0.1731 (8)	0.1638 (4)	0.056 (2)
C2	0.4049 (6)	0.3538 (7)	0.2822 (4)	0.0541 (19)
C3	0.5206 (5)	0.1754 (6)	0.2302 (4)	0.0438 (17)
C4	0.5034 (5)	0.2591 (6)	0.2915 (4)	0.0432 (17)
C5	0.5786 (5)	0.2591 (6)	0.3546 (4)	0.0471 (18)
C6	0.6718 (5)	0.1788 (7)	0.3581 (4)	0.0501 (18)
C7	0.6908 (5)	0.1006 (6)	0.2960 (4)	0.0522 (19)
C8	0.6138 (5)	0.0966 (6)	0.2343 (4)	0.0514 (19)
C9	0.2842 (6)	0.0614 (8)	0.1018 (4)	0.092 (3)
H9A	0.2345	0.1332	0.1029	0.138*
H9B	0.2420	−0.0154	0.1075	0.138*
H9C	0.3197	0.0597	0.0535	0.138*
C10	0.146 (3)	0.082 (4)	0.377 (3)	0.092 (10)	0.65 (3)
H10A	0.1269	0.0002	0.3975	0.110*	0.65 (3)
H10B	0.0798	0.1186	0.3504	0.110*	0.65 (3)
C11	0.1904 (17)	0.169 (2)	0.4401 (13)	0.105 (8)	0.65 (3)
H11A	0.2540	0.1306	0.4687	0.125*	0.65 (3)
H11B	0.2141	0.2496	0.4192	0.125*	0.65 (3)
C12	0.0942 (16)	0.188 (3)	0.4911 (12)	0.109 (7)	0.65 (3)
H12A	0.0279	0.2109	0.4602	0.164*	0.65 (3)
H12B	0.1124	0.2546	0.5274	0.164*	0.65 (3)
H12C	0.0806	0.1106	0.5183	0.164*	0.65 (3)
C10'	0.191 (5)	0.079 (9)	0.398 (5)	0.091 (18)	0.35 (3)
H10C	0.2502	0.0933	0.4382	0.109*	0.35 (3)
H10D	0.1521	0.0006	0.4103	0.109*	0.35 (3)
C11'	0.110 (3)	0.190 (4)	0.394 (2)	0.099 (14)	0.35 (3)
H11C	0.1282	0.2414	0.3501	0.119*	0.35 (3)
H11D	0.0349	0.1553	0.3821	0.119*	0.35 (3)
C12'	0.103 (4)	0.275 (4)	0.461 (4)	0.120 (16)	0.35 (3)
H12D	0.1432	0.2385	0.5045	0.180*	0.35 (3)
H12E	0.0251	0.2863	0.4720	0.180*	0.35 (3)
H12F	0.1348	0.3560	0.4490	0.180*	0.35 (3)
C13	0.5086 (7)	0.9088 (9)	0.4133 (5)	0.084 (3)
H13	0.5571	0.9195	0.4567	0.101*
C14	0.4573 (7)	0.7909 (8)	0.2986 (5)	0.111 (3)
H14A	0.3816	0.8159	0.3080	0.166*
H14B	0.4587	0.7021	0.2862	0.166*
H14C	0.4837	0.8393	0.2564	0.166*
C15	0.6236 (7)	0.7288 (8)	0.3804 (6)	0.113 (3)
H15A	0.6662	0.7546	0.4263	0.169*
H15B	0.6709	0.7317	0.3374	0.169*
H15C	0.5966	0.6437	0.3868	0.169*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0844 (6)	0.0688 (6)	0.0766 (6)	0.0133 (4)	−0.0017 (5)	−0.0155 (5)
Br2	0.0667 (5)	0.0806 (6)	0.0862 (7)	0.0101 (4)	−0.0205 (5)	0.0123 (5)
Br3	0.0556 (4)	0.0903 (7)	0.1302 (8)	0.0342 (5)	−0.0014 (5)	−0.0098 (6)
Br4	0.0749 (5)	0.0825 (6)	0.0923 (7)	0.0100 (5)	0.0163 (5)	−0.0266 (5)
N1	0.060 (4)	0.068 (4)	0.080 (5)	−0.008 (3)	−0.011 (4)	−0.011 (4)
N2	0.071 (4)	0.061 (4)	0.076 (5)	−0.011 (4)	−0.002 (4)	0.001 (4)
O1	0.057 (3)	0.063 (3)	0.068 (4)	−0.018 (3)	−0.009 (3)	0.002 (3)
O2	0.085 (4)	0.073 (4)	0.073 (4)	−0.007 (3)	−0.009 (3)	0.018 (3)
O3	0.034 (3)	0.057 (3)	0.124 (5)	0.003 (2)	−0.001 (3)	0.008 (3)
O4	0.055 (3)	0.038 (3)	0.128 (5)	0.003 (2)	−0.001 (3)	0.008 (3)
O5	0.098 (4)	0.076 (4)	0.097 (5)	0.026 (3)	−0.027 (4)	−0.012 (4)
C1	0.054 (4)	0.056 (6)	0.059 (6)	0.006 (4)	0.007 (4)	0.004 (5)
C2	0.045 (4)	0.054 (5)	0.062 (5)	0.007 (4)	−0.006 (4)	0.004 (4)
C3	0.035 (4)	0.044 (4)	0.053 (5)	−0.002 (3)	0.003 (4)	0.009 (4)
C4	0.030 (3)	0.042 (4)	0.057 (5)	−0.004 (3)	0.005 (4)	0.010 (4)
C5	0.039 (4)	0.045 (4)	0.058 (5)	0.002 (3)	0.001 (4)	0.006 (4)
C6	0.037 (4)	0.051 (4)	0.063 (5)	−0.002 (3)	0.004 (4)	0.014 (4)
C7	0.037 (4)	0.048 (5)	0.072 (6)	0.011 (3)	0.006 (4)	0.008 (4)
C8	0.042 (4)	0.041 (4)	0.071 (5)	0.000 (3)	0.007 (4)	0.010 (4)
C9	0.081 (5)	0.125 (7)	0.065 (6)	−0.034 (5)	−0.025 (5)	0.002 (6)
C10	0.09 (2)	0.078 (17)	0.11 (3)	0.005 (19)	−0.018 (18)	−0.008 (16)
C11	0.086 (13)	0.107 (17)	0.119 (17)	0.008 (11)	−0.011 (13)	−0.025 (14)
C12	0.099 (12)	0.12 (2)	0.107 (15)	−0.005 (15)	0.028 (11)	−0.008 (15)
C10'	0.08 (4)	0.09 (3)	0.10 (6)	0.01 (3)	−0.02 (3)	−0.01 (3)
C11'	0.08 (2)	0.11 (3)	0.11 (3)	0.01 (2)	−0.01 (2)	−0.01 (3)
C12'	0.12 (3)	0.08 (3)	0.15 (4)	0.01 (2)	0.00 (3)	−0.03 (3)
C13	0.083 (6)	0.078 (7)	0.088 (7)	0.002 (5)	−0.021 (6)	−0.011 (6)
C14	0.134 (8)	0.086 (7)	0.106 (8)	0.000 (6)	−0.046 (7)	−0.017 (6)
C15	0.096 (6)	0.093 (7)	0.149 (10)	0.032 (6)	−0.004 (6)	−0.011 (7)

Geometric parameters (Å, º) top

Br1—C5	1.890 (7)	C9—H9A	0.9600
Br2—C6	1.887 (6)	C9—H9B	0.9600
Br3—C7	1.889 (6)	C9—H9C	0.9600
Br4—C8	1.897 (7)	C10—C11	1.50 (6)
N1—C10'	1.47 (10)	C10—H10A	0.9700
N1—C10	1.50 (5)	C10—H10B	0.9700
N1—H1A	0.8900	C11—C12	1.50 (2)
N1—H1B	0.8900	C11—H11A	0.9700
N1—H1C	0.8900	C11—H11B	0.9700
N1—H1'A	0.8900	C12—H12A	0.9600
N1—H1'B	0.8900	C12—H12B	0.9600
N1—H1'C	0.8900	C12—H12C	0.9600
N2—C13	1.318 (9)	C10'—C11'	1.52 (10)
N2—C14	1.436 (8)	C10'—H10C	0.9700
N2—C15	1.450 (9)	C10'—H10D	0.9700
O1—C1	1.322 (8)	C11'—C12'	1.47 (5)
O1—C9	1.451 (7)	C11'—H11C	0.9700
O2—C1	1.198 (7)	C11'—H11D	0.9700
O3—C2	1.232 (7)	C12'—H12D	0.9600
O4—C2	1.220 (7)	C12'—H12E	0.9600
O5—C13	1.221 (9)	C12'—H12F	0.9600
C1—C3	1.495 (9)	C13—H13	0.9300
C2—C4	1.539 (8)	C14—H14A	0.9600
C3—C8	1.383 (8)	C14—H14B	0.9600
C3—C4	1.406 (8)	C14—H14C	0.9600
C4—C5	1.375 (8)	C15—H15A	0.9600
C5—C6	1.393 (8)	C15—H15B	0.9600
C6—C7	1.386 (9)	C15—H15C	0.9600
C7—C8	1.371 (8)

C10'—N1—C10	24.7 (18)	C7—C8—Br4	121.0 (5)
C10'—N1—H1A	107.3	C3—C8—Br4	117.5 (5)
C10—N1—H1A	109.5	O1—C9—H9A	109.5
C10'—N1—H1B	130.3	O1—C9—H9B	109.5
C10—N1—H1B	109.5	H9A—C9—H9B	109.5
H1A—N1—H1B	109.5	O1—C9—H9C	109.5
C10'—N1—H1C	87.9	H9A—C9—H9C	109.5
C10—N1—H1C	109.5	H9B—C9—H9C	109.5
H1A—N1—H1C	109.5	N1—C10—C11	106 (2)
H1B—N1—H1C	109.5	N1—C10—H10A	110.5
C10'—N1—H1'A	113.6	C11—C10—H10A	110.5
C10—N1—H1'A	91.3	N1—C10—H10B	110.5
H1A—N1—H1'A	113.6	C11—C10—H10B	110.5
H1B—N1—H1'A	18.7	H10A—C10—H10B	108.7
H1C—N1—H1'A	121.6	C12—C11—C10	105 (2)
C10'—N1—H1'B	109.9	C12—C11—H11A	110.6
C10—N1—H1'B	130.6	C10—C11—H11A	110.6
H1A—N1—H1'B	102.4	C12—C11—H11B	110.6
H1B—N1—H1'B	93.6	C10—C11—H11B	110.6
H1C—N1—H1'B	22.0	H11A—C11—H11B	108.8
H1'A—N1—H1'B	109.5	N1—C10'—C11'	106 (5)
C10'—N1—H1'C	104.9	N1—C10'—H10C	110.4
C10—N1—H1'C	104.3	C11'—C10'—H10C	110.4
H1A—N1—H1'C	7.2	N1—C10'—H10D	110.4
H1B—N1—H1'C	107.5	C11'—C10'—H10D	110.4
H1C—N1—H1'C	116.4	H10C—C10'—H10D	108.6
H1'A—N1—H1'C	109.5	C12'—C11'—C10'	119 (4)
H1'B—N1—H1'C	109.5	C12'—C11'—H11C	107.5
C13—N2—C14	121.0 (7)	C10'—C11'—H11C	107.5
C13—N2—C15	122.2 (8)	C12'—C11'—H11D	107.5
C14—N2—C15	116.9 (7)	C10'—C11'—H11D	107.5
C1—O1—C9	116.2 (6)	H11C—C11'—H11D	107.0
O2—C1—O1	125.3 (7)	C11'—C12'—H12D	109.5
O2—C1—C3	122.2 (7)	C11'—C12'—H12E	109.5
O1—C1—C3	112.5 (7)	H12D—C12'—H12E	109.5
O4—C2—O3	127.5 (6)	C11'—C12'—H12F	109.5
O4—C2—C4	116.8 (6)	H12D—C12'—H12F	109.5
O3—C2—C4	115.7 (6)	H12E—C12'—H12F	109.5
C8—C3—C4	119.1 (6)	O5—C13—N2	124.5 (8)
C8—C3—C1	122.7 (6)	O5—C13—H13	117.7
C4—C3—C1	118.2 (6)	N2—C13—H13	117.7
C5—C4—C3	119.2 (6)	N2—C14—H14A	109.5
C5—C4—C2	122.8 (6)	N2—C14—H14B	109.5
C3—C4—C2	117.9 (6)	H14A—C14—H14B	109.5
C4—C5—C6	121.1 (6)	N2—C14—H14C	109.5
C4—C5—Br1	119.1 (5)	H14A—C14—H14C	109.5
C6—C5—Br1	119.7 (5)	H14B—C14—H14C	109.5
C7—C6—C5	119.3 (6)	N2—C15—H15A	109.5
C7—C6—Br2	120.4 (5)	N2—C15—H15B	109.5
C5—C6—Br2	120.2 (6)	H15A—C15—H15B	109.5
C8—C7—C6	119.7 (6)	N2—C15—H15C	109.5
C8—C7—Br3	120.0 (6)	H15A—C15—H15C	109.5
C6—C7—Br3	120.3 (5)	H15B—C15—H15C	109.5
C7—C8—C3	121.4 (6)

C9—O1—C1—O2	0.1 (10)	C4—C5—C6—Br2	179.9 (5)
C9—O1—C1—C3	−179.8 (6)	Br1—C5—C6—Br2	−3.4 (7)
O2—C1—C3—C8	−106.3 (8)	C5—C6—C7—C8	−4.5 (10)
O1—C1—C3—C8	73.6 (8)	Br2—C6—C7—C8	177.6 (5)
O2—C1—C3—C4	75.4 (9)	C5—C6—C7—Br3	175.3 (5)
O1—C1—C3—C4	−104.8 (7)	Br2—C6—C7—Br3	−2.6 (8)
C8—C3—C4—C5	−1.0 (9)	C6—C7—C8—C3	4.3 (10)
C1—C3—C4—C5	177.4 (6)	Br3—C7—C8—C3	−175.5 (5)
C8—C3—C4—C2	174.8 (6)	C6—C7—C8—Br4	−178.6 (5)
C1—C3—C4—C2	−6.9 (9)	Br3—C7—C8—Br4	1.5 (7)
O4—C2—C4—C5	61.8 (9)	C4—C3—C8—C7	−1.5 (9)
O3—C2—C4—C5	−118.4 (7)	C1—C3—C8—C7	−179.9 (6)
O4—C2—C4—C3	−113.8 (7)	C4—C3—C8—Br4	−178.7 (4)
O3—C2—C4—C3	65.9 (9)	C1—C3—C8—Br4	3.0 (8)
C3—C4—C5—C6	0.8 (9)	C10'—N1—C10—C11	40 (10)
C2—C4—C5—C6	−174.8 (6)	N1—C10—C11—C12	176 (2)
C3—C4—C5—Br1	−175.9 (4)	C10—N1—C10'—C11'	−47 (9)
C2—C4—C5—Br1	8.6 (8)	N1—C10'—C11'—C12'	−141 (4)
C4—C5—C6—C7	2.0 (9)	C14—N2—C13—O5	−0.5 (13)
Br1—C5—C6—C7	178.6 (5)	C15—N2—C13—O5	179.4 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O3	0.89	1.87	2.757 (7)	175
N1—H1B···O4ⁱ	0.89	2.04	2.812 (8)	144
N1—H1C···O5ⁱⁱ	0.89	1.91	2.762 (8)	160

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

Experimental details

Crystal data
Chemical formula	C₃H₁₀N⁺·C₉H₃Br₄O₄⁻·C₃H₇NO
M_r	627.97
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	11.8964 (11), 10.5198 (10), 17.3743 (17)
β (°)	93.188 (1)
V (Å³)	2171.0 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	7.44
Crystal size (mm)	0.40 × 0.37 × 0.24

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1997)
T_min, T_max	0.155, 0.268
No. of measured, independent and observed [I > 2σ(I)] reflections	10672, 3821, 1836
R_int	0.069
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.104, 1.03
No. of reflections	3821
No. of parameters	268
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.57, −0.38

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O3	0.89	1.87	2.757 (7)	175
N1—H1B···O4ⁱ	0.89	2.04	2.812 (8)	144
N1—H1C···O5ⁱⁱ	0.89	1.91	2.762 (8)	160

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

Acknowledgements

The author thanks Shandong Provincial Natural Science Foundation, China (ZR2010BM033) for support.

References

Bruker (1997). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Li, J. (2011a). Acta Cryst. E67, o200. Web of Science CrossRef IUCr Journals Google Scholar
Li, J. (2011b). Acta Cryst. E67, o900. 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

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Volume 67| Part 6| June 2011| Page o1356

doi:10.1107/S1600536811016850

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

Propan-1-aminium 3,4,5,6-tetra­bromo-2-(meth­­oxy­carbon­yl)benzoate N,N-di­methyl­formamide monosolvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Propan-1-aminium 3,4,5,6-tetrabromo-2-(methoxycarbonyl)benzoate N,N-dimethylformamide monosolvate