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The title compound, C
8H
9BrN
2O
3, was synthesized by condensation of β-alanine methyl ester with 4-bromo-2-(trichloroacetyl)pyrrole, followed by saponification and acidification. In the molecule, all bond lengths and angles are normal. The crystal packing is stabilized by intermolecular N—H
O and O—H
O hydrogen bonds.
Supporting information
CCDC reference: 270311
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.005 Å
- R factor = 0.038
- wR factor = 0.104
- Data-to-parameter ratio = 17.1
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT431_ALERT_2_B Short Inter HL..A Contact Br1 .. O1 .. 3.05 Ang.
Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C8
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.46
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
5 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
3 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1999); cell refinement: SAINT-Plus (Bruker, 1999); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Bruker, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
3-(4-Bromo-1
H-pyrrole-2-carboxamido)propanoic acid
top
Crystal data top
C8H9BrN2O3 | F(000) = 260 |
Mr = 261.07 | Dx = 1.720 Mg m−3 |
Triclinic, P1 | Melting point: 430 K |
a = 7.768 (3) Å | Mo Kα radiation, λ = 0.71069 Å |
b = 8.497 (3) Å | Cell parameters from 946 reflections |
c = 9.342 (4) Å | θ = 2.9–27.0° |
α = 115.572 (6)° | µ = 4.06 mm−1 |
β = 99.093 (6)° | T = 298 K |
γ = 106.548 (6)° | Block, pale yellow |
V = 504.2 (3) Å3 | 0.50 × 0.45 × 0.20 mm |
Z = 2 | |
Data collection top
Bruker SMART 1K CCD area-detector diffractometer | 2168 independent reflections |
Radiation source: fine-focus sealed tube | 1951 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.034 |
φ and ω scans | θmax = 27.0°, θmin = 2.6° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −9→9 |
Tmin = 0.151, Tmax = 0.444 | k = −10→10 |
4276 measured reflections | l = −11→11 |
Refinement top
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)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.104 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0544P)2 + 0.3553P] where P = (Fo2 + 2Fc2)/3 |
2168 reflections | (Δ/σ)max < 0.001 |
127 parameters | Δρmax = 0.70 e Å−3 |
0 restraints | Δρmin = −0.86 e Å−3 |
Special details top
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 | x | y | z | Uiso*/Ueq | |
Br1 | 0.66284 (5) | 0.37822 (5) | 0.22181 (4) | 0.04658 (15) | |
N1 | 0.7742 (3) | 0.4726 (4) | 0.6926 (3) | 0.0377 (6) | |
HN1 | 0.8446 | 0.5307 | 0.7956 | 0.045* | |
N2 | 0.3472 (3) | 0.1328 (3) | 0.6666 (3) | 0.0342 (5) | |
HN2 | 0.2758 | 0.1095 | 0.5735 | 0.041* | |
O1 | 0.6345 (3) | 0.3000 (3) | 0.8664 (2) | 0.0422 (5) | |
O2 | −0.0350 (3) | 0.2836 (4) | 0.9458 (3) | 0.0521 (6) | |
H2A | −0.1379 | 0.2820 | 0.9062 | 0.078* | |
O3 | −0.0858 (4) | 0.0801 (4) | 0.6812 (3) | 0.0672 (8) | |
C1 | 0.6022 (4) | 0.3226 (4) | 0.6223 (3) | 0.0301 (5) | |
C2 | 0.5352 (4) | 0.2695 (4) | 0.4559 (3) | 0.0318 (6) | |
H2 | 0.4211 | 0.1716 | 0.3770 | 0.038* | |
C3 | 0.6713 (4) | 0.3910 (4) | 0.4286 (3) | 0.0337 (6) | |
C4 | 0.8170 (4) | 0.5159 (4) | 0.5762 (4) | 0.0398 (7) | |
H4 | 0.9257 | 0.6129 | 0.5933 | 0.048* | |
C5 | 0.5290 (4) | 0.2500 (4) | 0.7259 (3) | 0.0298 (5) | |
C6 | 0.2667 (5) | 0.0433 (5) | 0.7561 (4) | 0.0423 (7) | |
H6A | 0.3615 | 0.0140 | 0.8086 | 0.051* | |
H6B | 0.1601 | −0.0756 | 0.6760 | 0.051* | |
C7 | 0.1997 (4) | 0.1661 (5) | 0.8897 (4) | 0.0422 (7) | |
H7A | 0.1905 | 0.1208 | 0.9686 | 0.051* | |
H7B | 0.2948 | 0.2953 | 0.9510 | 0.051* | |
C8 | 0.0119 (4) | 0.1687 (4) | 0.8237 (4) | 0.0370 (6) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br1 | 0.0534 (2) | 0.0686 (3) | 0.0341 (2) | 0.03193 (18) | 0.01959 (15) | 0.03267 (18) |
N1 | 0.0287 (11) | 0.0455 (14) | 0.0193 (11) | 0.0049 (10) | 0.0040 (9) | 0.0077 (10) |
N2 | 0.0277 (11) | 0.0385 (12) | 0.0233 (11) | 0.0081 (10) | 0.0056 (9) | 0.0087 (10) |
O1 | 0.0293 (10) | 0.0706 (14) | 0.0205 (10) | 0.0164 (10) | 0.0066 (8) | 0.0204 (10) |
O2 | 0.0327 (11) | 0.0742 (16) | 0.0241 (10) | 0.0265 (11) | 0.0005 (8) | 0.0035 (11) |
O3 | 0.0414 (13) | 0.0868 (19) | 0.0248 (12) | 0.0198 (13) | −0.0051 (10) | −0.0028 (12) |
C1 | 0.0244 (12) | 0.0388 (14) | 0.0194 (12) | 0.0121 (11) | 0.0065 (9) | 0.0088 (11) |
C2 | 0.0268 (12) | 0.0395 (14) | 0.0190 (12) | 0.0122 (11) | 0.0033 (9) | 0.0084 (11) |
C3 | 0.0357 (14) | 0.0440 (15) | 0.0242 (13) | 0.0211 (12) | 0.0124 (11) | 0.0154 (12) |
C4 | 0.0336 (14) | 0.0413 (16) | 0.0354 (15) | 0.0084 (12) | 0.0145 (12) | 0.0145 (13) |
C5 | 0.0258 (12) | 0.0371 (14) | 0.0181 (12) | 0.0137 (11) | 0.0067 (9) | 0.0064 (10) |
C6 | 0.0408 (16) | 0.0404 (16) | 0.0439 (18) | 0.0146 (13) | 0.0212 (13) | 0.0183 (14) |
C7 | 0.0315 (14) | 0.0599 (19) | 0.0293 (15) | 0.0182 (14) | 0.0110 (11) | 0.0172 (14) |
C8 | 0.0239 (12) | 0.0454 (16) | 0.0232 (13) | 0.0040 (11) | 0.0054 (10) | 0.0090 (12) |
Geometric parameters (Å, º) top
Br1—C3 | 1.877 (3) | C1—C5 | 1.459 (4) |
N1—C4 | 1.347 (4) | C2—C3 | 1.393 (4) |
N1—C1 | 1.368 (4) | C2—H2 | 0.9300 |
N1—HN1 | 0.8600 | C3—C4 | 1.367 (4) |
N2—C5 | 1.330 (4) | C4—H4 | 0.9300 |
N2—C6 | 1.453 (4) | C6—C7 | 1.519 (4) |
N2—HN2 | 0.8600 | C6—H6A | 0.9700 |
O1—C5 | 1.248 (3) | C6—H6B | 0.9700 |
O2—C8 | 1.327 (4) | C7—C8 | 1.501 (4) |
O2—H2A | 0.8200 | C7—H7A | 0.9700 |
O3—C8 | 1.185 (4) | C7—H7B | 0.9700 |
C1—C2 | 1.377 (4) | | |
| | | |
C4—N1—C1 | 109.9 (2) | O1—C5—N2 | 121.8 (3) |
C4—N1—HN1 | 125.0 | O1—C5—C1 | 120.4 (2) |
C1—N1—HN1 | 125.0 | N2—C5—C1 | 117.9 (2) |
C5—N2—C6 | 121.3 (3) | N2—C6—C7 | 113.3 (3) |
C5—N2—HN2 | 119.3 | N2—C6—H6A | 108.9 |
C6—N2—HN2 | 119.3 | C7—C6—H6A | 108.9 |
C8—O2—H2A | 109.5 | N2—C6—H6B | 108.9 |
N1—C1—C2 | 107.4 (2) | C7—C6—H6B | 108.9 |
N1—C1—C5 | 119.2 (2) | H6A—C6—H6B | 107.7 |
C2—C1—C5 | 133.4 (3) | C8—C7—C6 | 114.7 (3) |
C1—C2—C3 | 106.7 (2) | C8—C7—H7A | 108.6 |
C1—C2—H2 | 126.6 | C6—C7—H7A | 108.6 |
C3—C2—H2 | 126.6 | C8—C7—H7B | 108.6 |
C4—C3—C2 | 108.6 (3) | C6—C7—H7B | 108.6 |
C4—C3—Br1 | 125.5 (2) | H7A—C7—H7B | 107.6 |
C2—C3—Br1 | 125.9 (2) | O3—C8—O2 | 122.8 (3) |
N1—C4—C3 | 107.4 (3) | O3—C8—C7 | 125.5 (3) |
N1—C4—H4 | 126.3 | O2—C8—C7 | 111.7 (2) |
C3—C4—H4 | 126.3 | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—HN1···O2i | 0.86 | 2.18 | 3.035 (2) | 171 |
N2—HN2···O3ii | 0.86 | 2.16 | 2.949 (2) | 153 |
O2—H2A···O1iii | 0.82 | 1.81 | 2.617 (2) | 167 |
Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) −x, −y, −z+1; (iii) x−1, y, z. |
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