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The title compound, C8H7Br3N2O3, was synthesized by condensation of β-alanine methyl ester with 3,4,5-tribromo-2-trichloro­acetyl­pyrrole at room temperature, followed by saponification and acidification. In the crystal structure, inter­molecular N—H...O hydrogen bonds and weak O—H...Br hydrogen-bond inter­actions link the mol­ecules into extended ribbons parallel to the c axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806016904/sg2024sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806016904/sg2024Isup2.hkl
Contains datablock I

CCDC reference: 610884

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.037
  • wR factor = 0.111
  • Data-to-parameter ratio = 15.9

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT415_ALERT_2_B Short Inter D-H..H-X H3 .. H7B .. 1.97 Ang.
Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR) is > 1.10 Tmin and Tmax reported: 0.050 0.072 Tmin and Tmax expected: 0.047 0.076 RR = 1.130 Please check that your absorption correction is appropriate. PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 1.058 Tmax scaled 0.076 Tmin scaled 0.053
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker,1999); cell refinement: SAINT-Plus (Bruker, 1999); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker,1997); software used to prepare material for publication: SHELXTL.

3-[(3,4,5-Tribromo-1H-pyrrol-2-ylcarbonyl)amino]propanoic acid top
Crystal data top
C8H7Br3N2O3F(000) = 396
Mr = 418.89Dx = 2.278 Mg m3
Triclinic, P1Melting point: 481 K
a = 7.0199 (10) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.0368 (12) ÅCell parameters from 2129 reflections
c = 11.5897 (16) Åθ = 2.6–25.9°
α = 97.019 (2)°µ = 9.90 mm1
β = 103.741 (2)°T = 273 K
γ = 102.156 (2)°Block, colorless
V = 610.61 (15) Å30.34 × 0.29 × 0.26 mm
Z = 2
Data collection top
Bruker SMART 1K CCD area-detector
diffractometer
2328 independent reflections
Radiation source: fine-focus sealed tube1837 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.025
φ and ω scansθmax = 26.0°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS; Sheldrick,1996)
h = 88
Tmin = 0.050, Tmax = 0.072k = 99
4506 measured reflectionsl = 1414
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0605P)2 + 0.8415P]
where P = (Fo2 + 2Fc2)/3
2328 reflections(Δ/σ)max = 0.001
146 parametersΔρmax = 0.80 e Å3
0 restraintsΔρmin = 0.81 e Å3
Special details top

Experimental. 1H NMR (DMSO6, 300 Hz): δ 12.61 (brs, 1H), 12.22 (brs, 1H), 8.13 (t, 1H), 3.49–3.35 (m, 2H), 2.46 (t, 2H); IR (KBr): 3401, 2929, 1698, 1638, 1551, 1511, 1426, 1243, 778; Analysis calculated for C8H7Br3N2O3: C 22.94, H 1.68, N 6.69%; found C 22.85, H 1.74, N 6.87.%

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
xyzUiso*/Ueq
Br10.18695 (9)0.14910 (9)0.92476 (6)0.0529 (2)
Br20.37542 (9)0.08757 (8)1.22695 (5)0.0484 (2)
Br30.90944 (9)0.29884 (10)1.32263 (5)0.0570 (2)
N10.7846 (6)0.3519 (5)1.0826 (4)0.0338 (10)
H10.90520.40821.08640.041*
C30.4575 (7)0.2267 (6)1.0165 (4)0.0292 (10)
C40.6208 (7)0.3218 (6)0.9845 (4)0.0314 (10)
C10.7286 (8)0.2799 (7)1.1724 (4)0.0364 (12)
C20.5276 (7)0.2024 (6)1.1357 (5)0.0333 (11)
N20.4886 (6)0.3699 (5)0.7844 (4)0.0349 (10)
H20.37070.32820.79320.042*
O10.8225 (6)0.4464 (6)0.8691 (4)0.0533 (11)
C50.6516 (7)0.3838 (6)0.8758 (4)0.0325 (11)
O30.2325 (6)0.0105 (5)0.4633 (4)0.0482 (10)
H30.33760.00600.44520.072*
O20.1316 (6)0.1865 (5)0.5846 (4)0.0501 (10)
C80.2643 (7)0.1510 (7)0.5417 (4)0.0339 (11)
C60.5028 (8)0.4224 (7)0.6713 (5)0.0388 (12)
H6A0.63490.49960.68270.047*
H6B0.40130.48540.64590.047*
C70.4722 (8)0.2676 (7)0.5728 (5)0.0382 (12)
H7A0.49600.30880.50090.046*
H7B0.57070.20230.59960.046*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0356 (3)0.0641 (4)0.0475 (4)0.0056 (3)0.0067 (3)0.0071 (3)
Br20.0557 (4)0.0481 (4)0.0446 (3)0.0027 (3)0.0252 (3)0.0146 (2)
Br30.0458 (4)0.0883 (5)0.0368 (3)0.0174 (3)0.0034 (3)0.0250 (3)
N10.026 (2)0.046 (3)0.027 (2)0.0028 (19)0.0075 (17)0.0099 (18)
C30.025 (2)0.030 (2)0.031 (2)0.0031 (19)0.0071 (19)0.0047 (19)
C40.034 (3)0.032 (3)0.029 (2)0.011 (2)0.011 (2)0.003 (2)
C10.041 (3)0.043 (3)0.027 (2)0.014 (2)0.009 (2)0.010 (2)
C20.035 (3)0.031 (3)0.035 (3)0.006 (2)0.013 (2)0.005 (2)
N20.029 (2)0.040 (2)0.031 (2)0.0007 (18)0.0051 (17)0.0087 (18)
O10.032 (2)0.083 (3)0.038 (2)0.006 (2)0.0065 (17)0.024 (2)
C50.030 (3)0.032 (3)0.028 (2)0.002 (2)0.003 (2)0.0013 (19)
O30.045 (2)0.045 (2)0.051 (2)0.0030 (18)0.0205 (19)0.0063 (18)
O20.036 (2)0.059 (3)0.047 (2)0.0061 (19)0.0110 (18)0.0091 (19)
C80.035 (3)0.041 (3)0.026 (2)0.011 (2)0.005 (2)0.007 (2)
C60.038 (3)0.040 (3)0.033 (3)0.002 (2)0.005 (2)0.012 (2)
C70.037 (3)0.044 (3)0.034 (3)0.005 (2)0.014 (2)0.010 (2)
Geometric parameters (Å, º) top
Br1—C31.873 (5)N2—H20.8600
Br2—C21.863 (5)O1—C51.224 (6)
Br3—C11.863 (5)O3—C81.303 (6)
N1—C11.348 (6)O3—H30.8200
N1—C41.366 (6)O2—C81.223 (6)
N1—H10.8600C8—C71.493 (7)
C3—C41.392 (7)C6—C71.523 (8)
C3—C21.404 (7)C6—H6A0.9700
C4—C51.456 (7)C6—H6B0.9700
C1—C21.357 (7)C7—H7A0.9700
N2—C51.336 (6)C7—H7B0.9700
N2—C61.444 (6)
C1—N1—C4109.7 (4)O1—C5—C4120.5 (4)
C1—N1—H1125.1N2—C5—C4118.1 (4)
C4—N1—H1125.1C8—O3—H3109.5
C4—C3—C2107.9 (4)O2—C8—O3122.2 (5)
C4—C3—Br1128.1 (4)O2—C8—C7122.4 (5)
C2—C3—Br1123.9 (4)O3—C8—C7115.3 (4)
N1—C4—C3106.3 (4)N2—C6—C7111.8 (4)
N1—C4—C5118.2 (4)N2—C6—H6A109.3
C3—C4—C5135.4 (4)C7—C6—H6A109.3
N1—C1—C2109.4 (4)N2—C6—H6B109.3
N1—C1—Br3122.4 (4)C7—C6—H6B109.3
C2—C1—Br3128.2 (4)H6A—C6—H6B107.9
C1—C2—C3106.6 (4)C8—C7—C6112.4 (4)
C1—C2—Br2126.4 (4)C8—C7—H7A109.1
C3—C2—Br2127.0 (4)C6—C7—H7A109.1
C5—N2—C6122.5 (4)C8—C7—H7B109.1
C5—N2—H2118.7C6—C7—H7B109.1
C6—N2—H2118.7H7A—C7—H7B107.9
O1—C5—N2121.4 (5)
C1—N1—C4—C30.1 (6)Br1—C3—C2—C1178.3 (4)
C1—N1—C4—C5177.7 (4)C4—C3—C2—Br2178.9 (4)
C2—C3—C4—N10.5 (5)Br1—C3—C2—Br21.3 (7)
Br1—C3—C4—N1178.0 (4)C6—N2—C5—O11.9 (8)
C2—C3—C4—C5177.5 (5)C6—N2—C5—C4178.0 (5)
Br1—C3—C4—C55.0 (9)N1—C4—C5—O16.7 (7)
C4—N1—C1—C20.4 (6)C3—C4—C5—O1170.0 (6)
C4—N1—C1—Br3178.3 (4)N1—C4—C5—N2173.4 (4)
N1—C1—C2—C30.7 (6)C3—C4—C5—N29.9 (9)
Br3—C1—C2—C3178.4 (4)C5—N2—C6—C7102.4 (5)
N1—C1—C2—Br2178.9 (4)O2—C8—C7—C65.7 (7)
Br3—C1—C2—Br21.2 (8)O3—C8—C7—C6175.9 (4)
C4—C3—C2—C10.7 (6)N2—C6—C7—C864.4 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···Br2i0.822.753.217 (4)118
N1—H1···O1ii0.861.932.777 (5)168
Symmetry codes: (i) x, y, z1; (ii) x+2, y+1, z+2.
 

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