Propan-1-aminium 3,4,5,6-tetra-bromo-2-(meth-oxy-carbon-yl)benzoate N,N-dimethyl-formamide monosolvate.

In the anion of the title solvated molecular salt, C(3)H(10)N(+)·C(9)H(3)Br(4)O(4) (-)·C(3)H(7)NO, the dihedral angles formed by the aromatic ring and the mean planes of the carboxyl-ate and meth-oxy-carbonyl 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 = 627.97

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.104

S = 1.03

3821 reflections

268 parameters

H-atom parameters constrained

Δρmax = 0.57 e Å−3

Δρmin = −0.38 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 ▶); software used to prepare material for publication: SHELXTL.

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

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

Supplementary material file. DOI: 10.1107/S1600536811016850/bt5538Isup3.cml

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

C3H10N+·C9H3Br4O4−·C3H7NO	F(000) = 1216
Mr = 627.97	Dx = 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

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

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(Fo2) + (0.0346P)2] where P = (Fo2 + 2Fc2)/3
3821 reflections	(Δ/σ)max = 0.001
268 parameters	Δρmax = 0.57 e Å−3
0 restraints	Δρmin = −0.38 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	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*

	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)

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)

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

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) ; (ii) .