4-Bromo-anilinium hydrogen phthalate.

In the anion of the title compound, C(6)H(7)BrN(+)·C(8)H(5)O(4) (-), the dihedral angles formed by the benzene ring and the mean planes of the -COOH and -COO(-) groups are 20.6 (3) and 83.2 (3)°, respectively. In the crystal, inter-molecular N-H⋯O and O-H⋯O hydrogen bonds connect the cations and anions, forming a two-dimensional network parallel to (001).

Related literature

For applications of phthalimides and N-substituted phthalimides, see: Lima et al. (2002 ▶). For the crystal structures of 4-chloro­anilinium, 2-hy­droxy­anilinium and 3-hy­droxy­anilinium hydrogen phthalates, see: Jagan & Sivakumar (2009 ▶).

Experimental

Crystal data

C6H7BrN+·C8H5O4 −

M = 338.16

Monoclinic,

a = 13.0890 (14) Å

b = 7.6670 (7) Å

c = 14.6900 (14) Å

β = 106.671 (1)°

V = 1412.2 (2) Å3

Z = 4

Mo Kα radiation

μ = 2.92 mm−1

T = 298 K

0.41 × 0.37 × 0.18 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1997 ▶) T min = 0.380, T max = 0.621

3555 measured reflections

2364 independent reflections

1659 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.127

S = 0.94

2364 reflections

186 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.82 e Å−3

Δρmin = −0.51 e Å−3

Absolute structure: Flack (1983 ▶), 1027 Friedel pairs

Flack parameter: 0.012 (16)

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/S1600536811017727/lh5245sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811017727/lh5245Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811017727/lh5245Isup3.cml

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

C6H7BrN+·C8H5O4−	F(000) = 680
Mr = 338.16	Dx = 1.590 Mg m−3
Monoclinic, C2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2y	Cell parameters from 1173 reflections
a = 13.0890 (14) Å	θ = 2.9–20.8°
b = 7.6670 (7) Å	µ = 2.92 mm−1
c = 14.6900 (14) Å	T = 298 K
β = 106.671 (1)°	Block, colorless
V = 1412.2 (2) Å3	0.41 × 0.37 × 0.18 mm
Z = 4

Bruker SMART CCD diffractometer	2364 independent reflections
Radiation source: fine-focus sealed tube	1659 reflections with I > 2σ(I)
graphite	Rint = 0.045
φ and ω scans	θmax = 25.0°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −13→15
Tmin = 0.380, Tmax = 0.621	k = −8→9
3555 measured reflections	l = −17→13

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)] = 0.054	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.127	w = 1/[σ2(Fo2) + (0.0642P)2] where P = (Fo2 + 2Fc2)/3
S = 0.94	(Δ/σ)max < 0.001
2364 reflections	Δρmax = 0.82 e Å−3
186 parameters	Δρmin = −0.51 e Å−3
1 restraint	Absolute structure: Flack (1983), 1027 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.012 (16)

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	0.16160 (6)	0.43398 (15)	0.05674 (5)	0.0677 (3)
N1	0.3761 (4)	−0.0249 (6)	0.4004 (3)	0.0329 (13)
H1A	0.3407	−0.1253	0.3952	0.049*
H1B	0.3731	0.0303	0.4528	0.049*
H1C	0.4438	−0.0462	0.4035	0.049*
O1	0.5651 (4)	0.7623 (6)	0.4163 (4)	0.0553 (16)
O2	0.6767 (3)	0.5378 (6)	0.4617 (4)	0.0377 (12)
H2	0.699 (4)	0.569 (9)	0.516 (4)	0.03 (2)*
O3	0.7303 (3)	0.1975 (5)	0.3875 (3)	0.0324 (10)
O4	0.5788 (4)	0.1691 (7)	0.4309 (4)	0.0385 (12)
C1	0.5990 (5)	0.6178 (9)	0.4009 (6)	0.0345 (18)
C2	0.6314 (5)	0.2287 (7)	0.3804 (5)	0.0255 (15)
C3	0.5581 (5)	0.5282 (9)	0.3075 (6)	0.0307 (17)
C4	0.5732 (5)	0.3475 (9)	0.2962 (5)	0.0297 (17)
C5	0.5343 (5)	0.2691 (11)	0.2082 (5)	0.044 (2)
H5	0.5446	0.1504	0.2013	0.053*
C6	0.4791 (6)	0.3685 (13)	0.1293 (6)	0.056 (3)
H6	0.4520	0.3151	0.0704	0.067*
C7	0.4648 (6)	0.5461 (13)	0.1385 (7)	0.056 (2)
H7	0.4297	0.6127	0.0859	0.067*
C8	0.5031 (5)	0.6231 (10)	0.2269 (6)	0.043 (2)
H8	0.4920	0.7418	0.2329	0.052*
C9	0.3276 (4)	0.0844 (8)	0.3171 (4)	0.0305 (15)
C10	0.3175 (5)	0.2651 (8)	0.3301 (5)	0.0342 (16)
H10	0.3433	0.3149	0.3901	0.041*
C11	0.2688 (4)	0.3668 (9)	0.2525 (5)	0.0403 (17)
H11	0.2614	0.4862	0.2598	0.048*
C12	0.2314 (5)	0.2920 (9)	0.1649 (5)	0.0378 (17)
C13	0.2417 (5)	0.1129 (9)	0.1509 (5)	0.0425 (17)
H13	0.2166	0.0638	0.0908	0.051*
C14	0.2908 (4)	0.0107 (8)	0.2296 (5)	0.0356 (16)
H14	0.2983	−0.1086	0.2223	0.043*

	U11	U22	U33	U12	U13	U23
Br1	0.0717 (5)	0.0667 (6)	0.0567 (5)	0.0124 (6)	0.0056 (3)	0.0159 (6)
N1	0.033 (2)	0.020 (3)	0.047 (3)	−0.002 (2)	0.013 (2)	−0.003 (2)
O1	0.052 (3)	0.027 (3)	0.082 (4)	0.015 (2)	0.011 (3)	−0.012 (3)
O2	0.035 (2)	0.024 (2)	0.045 (3)	0.0035 (19)	−0.002 (2)	−0.009 (2)
O3	0.025 (2)	0.021 (2)	0.050 (3)	0.0016 (17)	0.0098 (19)	0.001 (2)
O4	0.033 (2)	0.040 (3)	0.043 (3)	−0.007 (2)	0.013 (2)	0.004 (2)
C1	0.019 (3)	0.030 (4)	0.055 (5)	0.002 (3)	0.011 (3)	0.005 (3)
C2	0.029 (4)	0.011 (3)	0.036 (4)	−0.002 (2)	0.008 (3)	−0.007 (2)
C3	0.016 (3)	0.036 (4)	0.040 (4)	0.004 (3)	0.007 (3)	0.007 (3)
C4	0.032 (4)	0.022 (4)	0.034 (5)	−0.004 (3)	0.006 (3)	0.007 (3)
C5	0.043 (4)	0.043 (5)	0.044 (5)	−0.007 (3)	0.009 (4)	−0.004 (4)
C6	0.043 (4)	0.074 (7)	0.044 (5)	−0.013 (4)	0.001 (4)	−0.002 (4)
C7	0.039 (4)	0.066 (7)	0.054 (6)	−0.008 (4)	−0.001 (4)	0.017 (5)
C8	0.033 (4)	0.027 (4)	0.063 (6)	0.003 (3)	0.003 (4)	0.014 (4)
C9	0.021 (3)	0.035 (4)	0.037 (4)	−0.003 (3)	0.010 (3)	0.008 (3)
C10	0.032 (3)	0.030 (4)	0.038 (4)	−0.002 (3)	0.005 (3)	−0.004 (3)
C11	0.036 (3)	0.034 (4)	0.050 (5)	0.005 (3)	0.012 (3)	0.005 (3)
C12	0.033 (3)	0.041 (5)	0.038 (4)	0.003 (3)	0.007 (3)	0.008 (3)
C13	0.036 (4)	0.052 (5)	0.038 (4)	−0.004 (3)	0.008 (3)	−0.007 (3)
C14	0.037 (3)	0.024 (4)	0.045 (4)	0.000 (3)	0.012 (3)	−0.006 (3)

Br1—C12	1.927 (6)	C5—H5	0.9300
N1—C9	1.468 (8)	C6—C7	1.386 (12)
N1—H1A	0.8900	C6—H6	0.9300
N1—H1B	0.8900	C7—C8	1.382 (11)
N1—H1C	0.8900	C7—H7	0.9300
O1—C1	1.238 (8)	C8—H8	0.9300
O2—C1	1.299 (8)	C9—C14	1.359 (8)
O2—H2	0.80 (6)	C9—C10	1.410 (9)
O3—C2	1.292 (7)	C10—C11	1.377 (9)
O4—C2	1.236 (8)	C10—H10	0.9300
C1—C3	1.490 (11)	C11—C12	1.365 (9)
C2—C4	1.548 (9)	C11—H11	0.9300
C3—C8	1.400 (10)	C12—C13	1.400 (10)
C3—C4	1.415 (8)	C13—C14	1.392 (9)
C4—C5	1.385 (11)	C13—H13	0.9300
C5—C6	1.402 (12)	C14—H14	0.9300
C9—N1—H1A	109.5	C8—C7—C6	119.2 (9)
C9—N1—H1B	109.5	C8—C7—H7	120.4
H1A—N1—H1B	109.5	C6—C7—H7	120.4
C9—N1—H1C	109.5	C7—C8—C3	122.2 (8)
H1A—N1—H1C	109.5	C7—C8—H8	118.9
H1B—N1—H1C	109.5	C3—C8—H8	118.9
C1—O2—H2	122 (5)	C14—C9—C10	121.0 (6)
O1—C1—O2	123.2 (7)	C14—C9—N1	120.1 (6)
O1—C1—C3	121.9 (7)	C10—C9—N1	118.9 (6)
O2—C1—C3	114.8 (6)	C11—C10—C9	118.9 (6)
O4—C2—O3	127.0 (6)	C11—C10—H10	120.5
O4—C2—C4	117.8 (6)	C9—C10—H10	120.5
O3—C2—C4	115.2 (5)	C12—C11—C10	119.9 (6)
C8—C3—C4	117.7 (8)	C12—C11—H11	120.1
C8—C3—C1	120.1 (7)	C10—C11—H11	120.1
C4—C3—C1	122.2 (7)	C11—C12—C13	121.8 (6)
C5—C4—C3	120.5 (8)	C11—C12—Br1	119.8 (5)
C5—C4—C2	117.1 (6)	C13—C12—Br1	118.4 (5)
C3—C4—C2	122.4 (7)	C14—C13—C12	118.1 (6)
C4—C5—C6	120.0 (8)	C14—C13—H13	121.0
C4—C5—H5	120.0	C12—C13—H13	121.0
C6—C5—H5	120.0	C9—C14—C13	120.4 (6)
C7—C6—C5	120.3 (9)	C9—C14—H14	119.8
C7—C6—H6	119.8	C13—C14—H14	119.8
C5—C6—H6	119.8
O1—C1—C3—C8	18.0 (10)	C5—C6—C7—C8	−1.6 (13)
O2—C1—C3—C8	−157.9 (6)	C6—C7—C8—C3	1.3 (12)
O1—C1—C3—C4	−162.5 (7)	C4—C3—C8—C7	−0.3 (10)
O2—C1—C3—C4	21.7 (9)	C1—C3—C8—C7	179.3 (7)
C8—C3—C4—C5	−0.2 (10)	C14—C9—C10—C11	0.4 (9)
C1—C3—C4—C5	−179.8 (6)	N1—C9—C10—C11	−177.8 (5)
C8—C3—C4—C2	−179.1 (5)	C9—C10—C11—C12	0.0 (9)
C1—C3—C4—C2	1.3 (10)	C10—C11—C12—C13	−0.5 (10)
O4—C2—C4—C5	−95.0 (7)	C10—C11—C12—Br1	179.2 (4)
O3—C2—C4—C5	82.4 (7)	C11—C12—C13—C14	0.7 (9)
O4—C2—C4—C3	83.9 (8)	Br1—C12—C13—C14	−179.0 (4)
O3—C2—C4—C3	−98.7 (7)	C10—C9—C14—C13	−0.2 (8)
C3—C4—C5—C6	−0.1 (11)	N1—C9—C14—C13	178.0 (5)
C2—C4—C5—C6	178.9 (6)	C12—C13—C14—C9	−0.3 (9)
C4—C5—C6—C7	1.0 (12)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O3i	0.80 (6)	1.76 (6)	2.518 (6)	158 (7)
N1—H1C···O4	0.89	2.37	2.962 (7)	125
N1—H1C···O1ii	0.89	2.13	2.916 (7)	147
N1—H1B···O4iii	0.89	1.96	2.804 (7)	159
N1—H1A···O3iv	0.89	1.96	2.828 (6)	164

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O3i	0.80 (6)	1.76 (6)	2.518 (6)	158 (7)
N1—H1C⋯O4	0.89	2.37	2.962 (7)	125
N1—H1C⋯O1ii	0.89	2.13	2.916 (7)	147
N1—H1B⋯O4iii	0.89	1.96	2.804 (7)	159
N1—H1A⋯O3iv	0.89	1.96	2.828 (6)	164

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