Buy article online - an online subscription or single-article purchase is required to access this article.
The title compound, C
9H
10Br
2N
2O
3, was synthesized by condensation of β-alanine methyl ester with 4,5-dibromo-1-methyl-2-trichloroacetylpyrrole at room temperature, followed by saponification and acidification. In the crystal structure, intermolecular N—H
O and O—H
O hydrogen-bond interactions link the molecules into extended ribbons parallel to the
a axis.
Supporting information
CCDC reference: 277778
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean (C-C) = 0.005 Å
- R factor = 0.034
- wR factor = 0.085
- Data-to-parameter ratio = 17.8
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT431_ALERT_2_B Short Inter HL..A Contact Br1 .. O1 .. 3.02 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 C9
PLAT431_ALERT_2_C Short Inter HL..A Contact Br2 .. O2 .. 3.21 Ang.
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
4 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
1 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-[(4,5-Dibromo-1-methyl-1
H-pyrrole-2-carbonyl)amino]propanoic acid
top
Crystal data top
C9H10Br2N2O3 | F(000) = 344 |
Mr = 354.01 | Dx = 1.947 Mg m−3 |
Triclinic, P1 | Melting point: 458 K |
a = 7.752 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.238 (3) Å | Cell parameters from 816 reflections |
c = 9.304 (3) Å | θ = 3.3–27.0° |
α = 104.062 (5)° | µ = 6.70 mm−1 |
β = 107.942 (5)° | T = 273 K |
γ = 95.651 (5)° | Block, colourless |
V = 604.0 (3) Å3 | 0.50 × 0.38 × 0.20 mm |
Z = 2 | |
Data collection top
Bruker SMART 1K CCD area-detector diffractometer | 2602 independent reflections |
Radiation source: fine-focus sealed tube | 2039 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.023 |
φ and ω scans | θmax = 27.1°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −9→9 |
Tmin = 0.059, Tmax = 0.262 | k = −11→11 |
5185 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)] = 0.035 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.085 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0373P)2 + 0.6113P] where P = (Fo2 + 2Fc2)/3 |
2602 reflections | (Δ/σ)max < 0.001 |
146 parameters | Δρmax = 0.93 e Å−3 |
0 restraints | Δρmin = −0.60 e Å−3 |
Special details top
Experimental. Since the collected data were relatively weak, a large amount of reflections
with small intensities were marked as unobserved and excluded from the data
set by the diffractometer data reduction software. This affects the fraction
of unique reflections observed (out to θ=26°) which is equal to 91%. |
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 | 0.61258 (6) | 0.14878 (4) | 0.32445 (6) | 0.05795 (15) | |
Br2 | 0.89427 (5) | 0.46049 (5) | 0.65444 (5) | 0.05604 (15) | |
O1 | 0.6088 (3) | 0.8114 (3) | 0.2384 (3) | 0.0515 (7) | |
O2 | −0.0840 (4) | 0.6678 (3) | 0.0559 (3) | 0.0558 (7) | |
O3 | −0.0691 (4) | 0.8966 (3) | 0.2079 (5) | 0.0787 (10) | |
H3 | −0.1665 | 0.8562 | 0.2110 | 0.118* | |
N1 | 0.7019 (4) | 0.6056 (3) | 0.4346 (3) | 0.0385 (6) | |
N2 | 0.3377 (4) | 0.6532 (3) | 0.1060 (3) | 0.0415 (7) | |
H2 | 0.2715 | 0.5664 | 0.0894 | 0.050* | |
C1 | 0.7272 (4) | 0.4719 (4) | 0.4668 (4) | 0.0387 (7) | |
C2 | 0.6151 (5) | 0.3555 (4) | 0.3431 (4) | 0.0398 (8) | |
C3 | 0.5138 (5) | 0.4178 (4) | 0.2292 (4) | 0.0395 (8) | |
H3A | 0.4253 | 0.3644 | 0.1321 | 0.047* | |
C4 | 0.5690 (4) | 0.5725 (4) | 0.2870 (4) | 0.0358 (7) | |
C5 | 0.7964 (6) | 0.7559 (4) | 0.5432 (5) | 0.0567 (10) | |
H5A | 0.8065 | 0.7566 | 0.6488 | 0.085* | |
H5B | 0.7272 | 0.8311 | 0.5138 | 0.085* | |
H5C | 0.9176 | 0.7784 | 0.5381 | 0.085* | |
C6 | 0.5080 (4) | 0.6882 (4) | 0.2094 (4) | 0.0364 (7) | |
C7 | 0.2586 (5) | 0.7570 (5) | 0.0194 (5) | 0.0492 (9) | |
H7A | 0.1670 | 0.6985 | −0.0811 | 0.059* | |
H7B | 0.3551 | 0.8140 | −0.0018 | 0.059* | |
C8 | 0.1698 (5) | 0.8663 (4) | 0.1092 (5) | 0.0542 (10) | |
H8A | 0.2564 | 0.9125 | 0.2155 | 0.065* | |
H8B | 0.1466 | 0.9466 | 0.0593 | 0.065* | |
C9 | −0.0071 (5) | 0.7969 (4) | 0.1189 (5) | 0.0452 (9) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br1 | 0.0519 (3) | 0.0375 (2) | 0.0907 (3) | 0.01081 (17) | 0.0226 (2) | 0.0309 (2) |
Br2 | 0.0462 (2) | 0.0800 (3) | 0.0483 (2) | 0.0175 (2) | 0.01593 (17) | 0.0280 (2) |
O1 | 0.0406 (14) | 0.0335 (13) | 0.0810 (19) | 0.0048 (11) | 0.0185 (13) | 0.0212 (13) |
O2 | 0.0454 (15) | 0.0433 (15) | 0.0654 (17) | −0.0019 (12) | 0.0102 (13) | 0.0077 (13) |
O3 | 0.0583 (19) | 0.0440 (16) | 0.132 (3) | 0.0007 (14) | 0.051 (2) | 0.0025 (17) |
N1 | 0.0328 (15) | 0.0360 (15) | 0.0451 (16) | 0.0055 (12) | 0.0157 (13) | 0.0065 (12) |
N2 | 0.0364 (16) | 0.0349 (15) | 0.0547 (18) | 0.0071 (12) | 0.0146 (14) | 0.0170 (13) |
C1 | 0.0328 (17) | 0.0461 (19) | 0.0456 (19) | 0.0120 (15) | 0.0181 (15) | 0.0202 (16) |
C2 | 0.0351 (18) | 0.0340 (17) | 0.056 (2) | 0.0072 (14) | 0.0192 (16) | 0.0184 (16) |
C3 | 0.0334 (17) | 0.0314 (16) | 0.0496 (19) | 0.0044 (14) | 0.0105 (15) | 0.0099 (15) |
C4 | 0.0299 (16) | 0.0323 (16) | 0.0465 (18) | 0.0070 (13) | 0.0147 (14) | 0.0115 (14) |
C5 | 0.055 (2) | 0.040 (2) | 0.059 (2) | 0.0015 (18) | 0.012 (2) | −0.0027 (18) |
C6 | 0.0339 (18) | 0.0305 (16) | 0.0508 (19) | 0.0108 (14) | 0.0223 (15) | 0.0108 (14) |
C7 | 0.047 (2) | 0.051 (2) | 0.055 (2) | 0.0135 (17) | 0.0156 (18) | 0.0273 (18) |
C8 | 0.040 (2) | 0.042 (2) | 0.083 (3) | 0.0096 (17) | 0.020 (2) | 0.022 (2) |
C9 | 0.0356 (19) | 0.0365 (19) | 0.062 (2) | 0.0103 (15) | 0.0096 (17) | 0.0189 (17) |
Geometric parameters (Å, º) top
Br1—C2 | 1.872 (3) | C2—C3 | 1.395 (5) |
Br2—C1 | 1.860 (3) | C3—C4 | 1.371 (4) |
O1—C6 | 1.235 (4) | C3—H3A | 0.9300 |
O2—C9 | 1.194 (4) | C4—C6 | 1.467 (4) |
O3—C9 | 1.314 (5) | C5—H5A | 0.9600 |
O3—H3 | 0.8200 | C5—H5B | 0.9600 |
N1—C1 | 1.359 (4) | C5—H5C | 0.9600 |
N1—C4 | 1.380 (4) | C7—C8 | 1.507 (6) |
N1—C5 | 1.465 (5) | C7—H7A | 0.9700 |
N2—C6 | 1.325 (4) | C7—H7B | 0.9700 |
N2—C7 | 1.460 (4) | C8—C9 | 1.494 (5) |
N2—H2 | 0.8600 | C8—H8A | 0.9700 |
C1—C2 | 1.355 (5) | C8—H8B | 0.9700 |
| | | |
C9—O3—H3 | 109.5 | N1—C5—H5C | 109.5 |
C1—N1—C4 | 107.6 (3) | H5A—C5—H5C | 109.5 |
C1—N1—C5 | 124.7 (3) | H5B—C5—H5C | 109.5 |
C4—N1—C5 | 127.7 (3) | O1—C6—N2 | 121.7 (3) |
C6—N2—C7 | 122.2 (3) | O1—C6—C4 | 122.2 (3) |
C6—N2—H2 | 118.9 | N2—C6—C4 | 116.1 (3) |
C7—N2—H2 | 118.9 | N2—C7—C8 | 112.2 (3) |
C2—C1—N1 | 109.4 (3) | N2—C7—H7A | 109.2 |
C2—C1—Br2 | 127.7 (3) | C8—C7—H7A | 109.2 |
N1—C1—Br2 | 122.9 (3) | N2—C7—H7B | 109.2 |
C1—C2—C3 | 107.6 (3) | C8—C7—H7B | 109.2 |
C1—C2—Br1 | 125.5 (3) | H7A—C7—H7B | 107.9 |
C3—C2—Br1 | 126.8 (3) | C9—C8—C7 | 114.8 (3) |
C4—C3—C2 | 107.2 (3) | C9—C8—H8A | 108.6 |
C4—C3—H3A | 126.4 | C7—C8—H8A | 108.6 |
C2—C3—H3A | 126.4 | C9—C8—H8B | 108.6 |
C3—C4—N1 | 108.2 (3) | C7—C8—H8B | 108.6 |
C3—C4—C6 | 128.2 (3) | H8A—C8—H8B | 107.5 |
N1—C4—C6 | 123.6 (3) | O2—C9—O3 | 123.4 (4) |
N1—C5—H5A | 109.5 | O2—C9—C8 | 125.4 (4) |
N1—C5—H5B | 109.5 | O3—C9—C8 | 111.2 (3) |
H5A—C5—H5B | 109.5 | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O1i | 0.82 | 1.86 | 2.663 (4) | 167 |
N2—H2···O2ii | 0.86 | 2.32 | 3.128 (4) | 157 |
Symmetry codes: (i) x−1, y, z; (ii) −x, −y+1, −z. |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
If you have already registered and are using a computer listed in your registration details, please email
support@iucr.org for assistance.