3-Bromo-anilinium picrate.

In the title compound, C(6)H(7)BrN(+)·C(6)H(2)N(3)O(7) (-), the O atoms of two of the nitro groups are disordered over two sites, the ratios of the refined occupancies being 0.72 (6):0.28 (6) and 0.74 (5):0.26 (5). In the crystal structure, the anions and cations are linked via inter-molecular N-H⋯O hydrogen bonds into chains along [100]. Further stabilization is provided by weak inter-molecular C-H⋯O hydrogen bonds.

Related literature

For background information on the crystallization of ammonium salts with picrate derivatives, see: Harrison et al. (2007 ▶); Pascard et al. (1982 ▶); Pearson et al. (2007 ▶); Wang et al. (2003 ▶).

Experimental

Crystal data

C6H7BrN+·C6H2N3O7 −

M = 401.14

Triclinic,

a = 4.3515 (3) Å

b = 12.0757 (8) Å

c = 14.0592 (9) Å

α = 87.783 (1)°

β = 85.945 (1)°

γ = 80.533 (1)°

V = 726.61 (8) Å3

Z = 2

Mo Kα radiation

μ = 2.88 mm−1

T = 298 K

0.16 × 0.12 × 0.10 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.646, T max = 0.762

4689 measured reflections

2818 independent reflections

2225 reflections with I > 2σ(I)

R int = 0.090

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.123

S = 0.96

2818 reflections

264 parameters

15 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.69 e Å−3

Δρmin = −0.59 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809048405/lh2949sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809048405/lh2949Isup2.hkl

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

C6H7BrN+·C6H2N3O7−	Z = 2
Mr = 401.14	F(000) = 400
Triclinic, P1	Dx = 1.833 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.3515 (3) Å	Cell parameters from 2179 reflections
b = 12.0757 (8) Å	θ = 2.3–27.6°
c = 14.0592 (9) Å	µ = 2.88 mm−1
α = 87.783 (1)°	T = 298 K
β = 85.945 (1)°	Block, yellow
γ = 80.533 (1)°	0.16 × 0.12 × 0.10 mm
V = 726.61 (8) Å3

Bruker SMART APEX CCD diffractometer	2818 independent reflections
Radiation source: fine focus sealed Siemens Mo tube	2225 reflections with I > 2σ(I)
graphite	Rint = 0.090
0.3° wide ω exposures scans	θmax = 26.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −5→5
Tmin = 0.646, Tmax = 0.762	k = −14→12
4689 measured reflections	l = −17→16

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) = 0.123	H atoms treated by a mixture of independent and constrained refinement
S = 0.96	w = 1/[σ2(Fo2) + (0.0686P)2] where P = (Fo2 + 2Fc2)/3
2818 reflections	(Δ/σ)max < 0.001
264 parameters	Δρmax = 0.69 e Å−3
15 restraints	Δρmin = −0.59 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	0.31978 (9)	1.44651 (3)	0.38403 (3)	0.0620 (2)
C1	0.2439 (7)	1.1358 (3)	0.2852 (2)	0.0365 (6)
C2	0.3254 (7)	1.2405 (3)	0.2916 (2)	0.0400 (7)
H2	0.4488	1.2694	0.2432	0.048*
C3	0.2197 (7)	1.3015 (3)	0.3716 (2)	0.0418 (7)
C4	0.0376 (8)	1.2589 (3)	0.4453 (2)	0.0488 (8)
H4	−0.0312	1.3006	0.4992	0.059*
C5	−0.0383 (8)	1.1533 (3)	0.4364 (2)	0.0500 (8)
H5	−0.1593	1.1236	0.4851	0.060*
C6	0.0623 (8)	1.0912 (3)	0.3568 (2)	0.0451 (7)
H6	0.0090	1.0204	0.3512	0.054*
C7	0.9423 (7)	0.8220 (3)	0.1767 (2)	0.0376 (7)
C8	0.7948 (7)	0.7451 (3)	0.2374 (2)	0.0401 (7)
C9	0.8229 (8)	0.6320 (3)	0.2218 (2)	0.0432 (7)
H9	0.7200	0.5862	0.2632	0.052*
C10	1.0069 (8)	0.5873 (3)	0.1436 (2)	0.0434 (7)
C11	1.1497 (7)	0.6552 (3)	0.0790 (2)	0.0433 (7)
H11	1.2660	0.6253	0.0253	0.052*
C12	1.1162 (7)	0.7672 (3)	0.0960 (2)	0.0398 (7)
N1	0.3525 (7)	1.0693 (2)	0.20133 (19)	0.0421 (6)
H1A	0.520 (5)	1.025 (3)	0.215 (2)	0.051*
H1B	0.400 (8)	1.110 (3)	0.1527 (17)	0.051*
H1C	0.229 (7)	1.025 (2)	0.187 (2)	0.051*
N2	0.6000 (7)	0.7845 (3)	0.32217 (19)	0.0484 (7)
N3	1.0392 (7)	0.4679 (3)	0.1282 (2)	0.0503 (7)
N4	1.2620 (7)	0.8348 (2)	0.02367 (18)	0.0490 (7)
O1	0.9193 (5)	0.9265 (2)	0.18883 (16)	0.0489 (6)
O2	0.623 (5)	0.8764 (8)	0.3531 (10)	0.066 (3)	0.72 (6)
O3	0.419 (6)	0.7259 (14)	0.3589 (15)	0.081 (4)	0.72 (6)
O2'	0.506 (13)	0.8824 (11)	0.334 (2)	0.074 (8)	0.28 (6)
O3'	0.555 (13)	0.7092 (12)	0.3811 (14)	0.058 (8)	0.28 (6)
O4	0.8643 (8)	0.4144 (2)	0.1743 (2)	0.0706 (8)
O5	1.2388 (7)	0.4267 (2)	0.0683 (2)	0.0661 (7)
O6	1.223 (5)	0.8179 (12)	−0.0605 (4)	0.068 (3)	0.74 (5)
O7	1.419 (3)	0.9014 (12)	0.0496 (6)	0.064 (3)	0.74 (5)
O6'	1.340 (11)	0.798 (3)	−0.0553 (15)	0.073 (8)	0.26 (5)
O7'	1.27 (2)	0.935 (3)	0.039 (3)	0.099 (14)	0.26 (5)

	U11	U22	U33	U12	U13	U23
Br1	0.0788 (3)	0.0419 (2)	0.0677 (3)	−0.01847 (19)	0.0063 (2)	−0.01619 (18)
C1	0.0392 (15)	0.0353 (16)	0.0344 (15)	−0.0054 (13)	0.0003 (12)	−0.0009 (12)
C2	0.0447 (16)	0.0371 (17)	0.0382 (15)	−0.0100 (14)	0.0045 (13)	0.0000 (13)
C3	0.0465 (17)	0.0359 (16)	0.0429 (16)	−0.0051 (14)	−0.0051 (13)	−0.0030 (13)
C4	0.059 (2)	0.050 (2)	0.0356 (16)	−0.0058 (16)	0.0021 (14)	−0.0039 (14)
C5	0.062 (2)	0.050 (2)	0.0379 (17)	−0.0161 (17)	0.0096 (15)	0.0034 (15)
C6	0.0538 (18)	0.0408 (18)	0.0416 (17)	−0.0132 (15)	0.0024 (14)	0.0018 (14)
C7	0.0412 (15)	0.0368 (17)	0.0363 (15)	−0.0098 (13)	−0.0032 (12)	−0.0045 (12)
C8	0.0424 (16)	0.0492 (19)	0.0296 (14)	−0.0107 (14)	0.0006 (12)	−0.0048 (13)
C9	0.0506 (18)	0.0424 (18)	0.0389 (16)	−0.0159 (15)	−0.0021 (13)	0.0025 (14)
C10	0.0568 (19)	0.0354 (17)	0.0389 (16)	−0.0107 (15)	−0.0024 (14)	−0.0016 (13)
C11	0.0495 (18)	0.0429 (18)	0.0375 (16)	−0.0091 (15)	0.0028 (13)	−0.0048 (14)
C12	0.0448 (16)	0.0412 (18)	0.0347 (15)	−0.0139 (14)	0.0033 (12)	0.0007 (13)
N1	0.0517 (16)	0.0350 (15)	0.0405 (14)	−0.0121 (12)	0.0048 (12)	−0.0042 (11)
N2	0.0560 (17)	0.0534 (19)	0.0354 (14)	−0.0103 (15)	0.0051 (12)	−0.0044 (14)
N3	0.0647 (18)	0.0412 (16)	0.0463 (15)	−0.0100 (14)	−0.0090 (14)	−0.0012 (13)
N4	0.0648 (18)	0.0423 (17)	0.0408 (16)	−0.0171 (14)	0.0113 (13)	−0.0026 (12)
O1	0.0499 (13)	0.0405 (13)	0.0580 (14)	−0.0141 (10)	0.0069 (10)	−0.0112 (11)
O2	0.092 (7)	0.048 (4)	0.053 (4)	−0.007 (3)	0.021 (4)	−0.012 (2)
O3	0.078 (8)	0.106 (5)	0.067 (6)	−0.051 (5)	0.035 (6)	−0.029 (4)
O2'	0.079 (18)	0.069 (10)	0.054 (11)	0.028 (8)	0.028 (10)	0.016 (7)
O3'	0.071 (16)	0.066 (8)	0.043 (7)	−0.032 (8)	0.010 (8)	−0.012 (5)
O4	0.099 (2)	0.0506 (16)	0.0676 (17)	−0.0332 (16)	0.0046 (15)	0.0009 (13)
O5	0.0760 (18)	0.0444 (15)	0.0747 (17)	−0.0016 (13)	0.0045 (14)	−0.0115 (13)
O6	0.106 (8)	0.061 (5)	0.040 (3)	−0.029 (5)	0.015 (3)	−0.006 (2)
O7	0.067 (4)	0.071 (5)	0.064 (3)	−0.039 (4)	0.003 (3)	−0.002 (3)
O6'	0.097 (18)	0.044 (9)	0.068 (11)	−0.001 (11)	0.047 (9)	−0.013 (7)
O7'	0.14 (4)	0.084 (13)	0.085 (14)	−0.067 (17)	0.039 (19)	−0.019 (12)

Br1—C3	1.890 (3)	C10—C11	1.383 (4)
C1—C2	1.376 (4)	C10—N3	1.449 (4)
C1—C6	1.382 (4)	C11—C12	1.365 (5)
C1—N1	1.459 (4)	C11—H11	0.9300
C2—C3	1.377 (4)	C12—N4	1.455 (4)
C2—H2	0.9300	N1—H1A	0.856 (10)
C3—C4	1.394 (4)	N1—H1B	0.862 (10)
C4—C5	1.382 (5)	N1—H1C	0.859 (10)
C4—H4	0.9300	N2—O2'	1.200 (10)
C5—C6	1.377 (5)	N2—O3	1.218 (5)
C5—H5	0.9300	N2—O2	1.229 (6)
C6—H6	0.9300	N2—O3'	1.237 (9)
C7—O1	1.266 (4)	N3—O4	1.215 (4)
C7—C8	1.435 (4)	N3—O5	1.223 (4)
C7—C12	1.439 (4)	N4—O6'	1.218 (10)
C8—C9	1.375 (5)	N4—O7	1.220 (6)
C8—N2	1.461 (4)	N4—O6	1.236 (6)
C9—C10	1.386 (4)	N4—O7'	1.240 (10)
C9—H9	0.9300
C2—C1—C6	121.6 (3)	C12—C11—H11	120.7
C2—C1—N1	119.5 (2)	C10—C11—H11	120.7
C6—C1—N1	118.8 (3)	C11—C12—C7	125.2 (3)
C1—C2—C3	118.4 (3)	C11—C12—N4	115.8 (3)
C1—C2—H2	120.8	C7—C12—N4	118.9 (3)
C3—C2—H2	120.8	C1—N1—H1A	108 (3)
C2—C3—C4	121.5 (3)	C1—N1—H1B	112 (2)
C2—C3—Br1	120.4 (2)	H1A—N1—H1B	107 (3)
C4—C3—Br1	118.1 (2)	C1—N1—H1C	114 (2)
C5—C4—C3	118.5 (3)	H1A—N1—H1C	104 (4)
C5—C4—H4	120.8	H1B—N1—H1C	111 (3)
C3—C4—H4	120.8	O2'—N2—O3	111.6 (16)
C6—C5—C4	121.0 (3)	O3—N2—O2	122.5 (6)
C6—C5—H5	119.5	O2'—N2—O3'	123.8 (14)
C4—C5—H5	119.5	O2—N2—O3'	117.4 (10)
C5—C6—C1	119.0 (3)	O2'—N2—C8	121.9 (12)
C5—C6—H6	120.5	O3—N2—C8	119.0 (4)
C1—C6—H6	120.5	O2—N2—C8	118.5 (5)
O1—C7—C8	125.7 (3)	O3'—N2—C8	114.2 (12)
O1—C7—C12	122.5 (3)	O4—N3—O5	123.5 (3)
C8—C7—C12	111.8 (3)	O4—N3—C10	118.4 (3)
C9—C8—C7	124.2 (3)	O5—N3—C10	118.1 (3)
C9—C8—N2	115.3 (3)	O6'—N4—O7	114.7 (18)
C7—C8—N2	120.5 (3)	O7—N4—O6	124.7 (6)
C8—C9—C10	119.1 (3)	O6'—N4—O7'	119.8 (15)
C8—C9—H9	120.5	O6—N4—O7'	113 (2)
C10—C9—H9	120.5	O6'—N4—C12	120.1 (15)
C11—C10—C9	121.1 (3)	O7—N4—C12	118.3 (4)
C11—C10—N3	120.0 (3)	O6—N4—C12	117.0 (6)
C9—C10—N3	118.9 (3)	O7'—N4—C12	119.6 (11)
C12—C11—C10	118.5 (3)	C7—O1—H1A	123.4 (12)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1C···O7i	0.86 (1)	2.50 (3)	2.966 (12)	115 (3)
N1—H1C···O1i	0.86 (1)	1.93 (1)	2.775 (4)	166 (3)
N1—H1A···O1	0.86 (1)	1.96 (2)	2.766 (4)	157 (3)
N1—H1B···O6ii	0.86 (1)	2.28 (2)	3.047 (12)	148 (3)
C11—H11···O5iii	0.93	2.45	3.296 (4)	152
C4—H4···O3iv	0.93	2.57	3.273 (7)	133

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1C⋯O7i	0.859 (10)	2.50 (3)	2.966 (12)	115 (3)
N1—H1C⋯O1i	0.859 (10)	1.934 (14)	2.775 (4)	166 (3)
N1—H1A⋯O1	0.856 (10)	1.958 (17)	2.766 (4)	157 (3)
N1—H1B⋯O6ii	0.862 (10)	2.28 (2)	3.047 (12)	148 (3)
C11—H11⋯O5iii	0.93	2.45	3.296 (4)	152
C4—H4⋯O3iv	0.93	2.57	3.273 (7)	133

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