4-Bromo-1H-pyrrole-2-carb-oxy-lic acid.

In the title compound, C(5)H(4)BrNO(2), the non-H atoms of the pyrrole ring and the Br atom are approximately coplanar, with an r.m.s. deviation from the best fit plane of 0.025 (6) Å;. The dihedral angle between the plane of the carb-oxy group and this plane is 14.1 (2)°. In the crystal, O-H⋯O hydrogen bonds link the mol-ecules together, forming corrugated sheets parallel to the bc plane.

Related literature

For pyrrole compounds obtained from marine organisms, see: Liu et al. (2005 ▶); Faulkner (2002 ▶). For the bioactivity of pyrrole derivatives, see: Banwell et al. (2006 ▶); Sosa et al. (2002 ▶). For related structures, see: Zeng et al. (2007 ▶); Tang et al. (2008 ▶).

Experimental

Crystal data

C5H4BrNO2

M = 190.00

Monoclinic,

a = 16.0028 (13) Å

b = 4.9046 (6) Å

c = 8.2367 (7) Å

β = 93.199 (7)°

V = 645.47 (11) Å3

Z = 4

Mo Kα radiation

μ = 6.29 mm−1

T = 293 K

0.24 × 0.20 × 0.14 mm

Data collection

Oxford Gemini S Ultra area-detector diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.314, T max = 0.473

2436 measured reflections

1387 independent reflections

1081 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.081

S = 1.10

1387 reflections

85 parameters

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.45 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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 datablock(s) I, global. DOI: 10.1107/S1600536812034800/fj2579sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812034800/fj2579Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812034800/fj2579Isup3.cml

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

C5H4BrNO2	F(000) = 368
Mr = 190.00	Dx = 1.955 Mg m−3
Monoclinic, P21/c	Melting point < 424 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 16.0028 (13) Å	Cell parameters from 950 reflections
b = 4.9046 (6) Å	θ = 3.5–29.1°
c = 8.2367 (7) Å	µ = 6.29 mm−1
β = 93.199 (7)°	T = 293 K
V = 645.47 (11) Å3	Block, light yellow
Z = 4	0.24 × 0.20 × 0.14 mm

Oxford Gemini S Ultra area-detector diffractometer	1387 independent reflections
Radiation source: fine-focus sealed tube	1081 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
φ and ω scans	θmax = 27.0°, θmin = 3.8°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	h = −20→12
Tmin = 0.314, Tmax = 0.473	k = −5→6
2436 measured reflections	l = −10→10

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.081	H-atom parameters constrained
S = 1.10	w = 1/[σ2(Fo2) + (0.034P)2 + 0.2705P] where P = (Fo2 + 2Fc2)/3
1387 reflections	(Δ/σ)max < 0.001
85 parameters	Δρmax = 0.39 e Å−3
0 restraints	Δρmin = −0.45 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	0.07690 (2)	0.68153 (9)	−0.16395 (4)	0.04763 (17)
N1	0.24925 (19)	0.3185 (6)	0.1354 (4)	0.0400 (7)
H1	0.2653	0.1983	0.2065	0.048*
C3	0.2505 (2)	0.6756 (8)	−0.0297 (4)	0.0321 (7)
H3	0.2674	0.8285	−0.0861	0.039*
O1	0.40382 (15)	0.4281 (6)	0.2816 (3)	0.0514 (7)
C4	0.29799 (19)	0.5248 (7)	0.0817 (4)	0.0321 (8)
C2	0.17094 (19)	0.5519 (8)	−0.0414 (4)	0.0327 (8)
O2	0.4311 (2)	0.7498 (8)	0.0940 (4)	0.0731 (10)
H2	0.4079	0.8099	0.0102	0.013 (15)*	0.50
H2'	0.4898	0.7973	0.1562	0.009 (13)*	0.50
C1	0.1716 (2)	0.3316 (8)	0.0598 (5)	0.0421 (9)
H1A	0.1274	0.2128	0.0743	0.050*
C5	0.3821 (2)	0.5608 (9)	0.1583 (4)	0.0373 (8)

	U11	U22	U33	U12	U13	U23
Br1	0.0310 (2)	0.0638 (3)	0.0466 (2)	0.00130 (19)	−0.01071 (15)	0.0010 (2)
N1	0.0398 (17)	0.0338 (17)	0.0453 (16)	0.0004 (15)	−0.0077 (13)	0.0041 (15)
C3	0.0309 (17)	0.037 (2)	0.0284 (15)	−0.0035 (16)	−0.0004 (12)	0.0005 (16)
O1	0.0376 (14)	0.0662 (19)	0.0487 (14)	0.0089 (14)	−0.0119 (11)	0.0072 (15)
C4	0.0274 (15)	0.036 (2)	0.0329 (15)	0.0019 (15)	−0.0013 (12)	−0.0050 (16)
C2	0.0279 (16)	0.041 (2)	0.0289 (15)	0.0017 (16)	−0.0025 (12)	−0.0053 (17)
O2	0.052 (2)	0.097 (3)	0.069 (2)	−0.0130 (18)	−0.0158 (16)	0.004 (2)
C1	0.0357 (19)	0.042 (2)	0.048 (2)	−0.0074 (17)	−0.0006 (16)	−0.0045 (19)
C5	0.0278 (17)	0.048 (2)	0.0357 (17)	0.0020 (18)	−0.0038 (13)	−0.0053 (19)

Br1—C2	1.876 (3)	O1—C5	1.239 (4)
N1—C1	1.360 (5)	C4—C5	1.465 (4)
N1—C4	1.366 (4)	C2—C1	1.364 (5)
N1—H1	0.8600	O2—C5	1.342 (5)
C3—C4	1.375 (5)	O2—H2	0.8200
C3—C2	1.408 (4)	O2—H2'	1.0702
C3—H3	0.9300	C1—H1A	0.9300
C1—N1—C4	109.9 (3)	C3—C2—Br1	125.8 (3)
C1—N1—H1	125.1	C5—O2—H2	109.5
C4—N1—H1	125.1	C5—O2—H2'	118.5
C4—C3—C2	106.1 (3)	H2—O2—H2'	132.0
C4—C3—H3	126.9	N1—C1—C2	107.1 (3)
C2—C3—H3	126.9	N1—C1—H1A	126.5
N1—C4—C3	108.1 (3)	C2—C1—H1A	126.5
N1—C4—C5	118.5 (3)	O1—C5—O2	122.9 (3)
C3—C4—C5	133.1 (3)	O1—C5—C4	119.9 (3)
C1—C2—C3	108.8 (3)	O2—C5—C4	117.1 (3)
C1—C2—Br1	125.2 (3)
C1—N1—C4—C3	0.6 (4)	C3—C2—C1—N1	0.8 (4)
C1—N1—C4—C5	175.0 (3)	Br1—C2—C1—N1	−175.1 (2)
C2—C3—C4—N1	−0.1 (4)	N1—C4—C5—O1	−8.7 (5)
C2—C3—C4—C5	−173.3 (3)	C3—C4—C5—O1	163.9 (4)
C4—C3—C2—C1	−0.5 (4)	N1—C4—C5—O2	174.5 (3)
C4—C3—C2—Br1	175.4 (2)	C3—C4—C5—O2	−12.8 (6)
C4—N1—C1—C2	−0.9 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2′···O1i	1.07	1.86	2.914 (4)	166
O2—H2···O1ii	0.82	2.28	3.030 (4)	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2′⋯O1i	1.07	1.86	2.914 (4)	166
O2—H2⋯O1ii	0.82	2.28	3.030 (4)	153

Symmetry codes: (i) ; (ii) .