Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807019289/hg2225sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807019289/hg2225Isup2.hkl |
CCDC reference: 648076
The hydrochloride of glycine methyl ester (0.63 g, 5 mmol) and 3,4,5-tribromo-2-trichloroacetylpyrrole (2.25 g, 5 mmol) were added to acetonitrile (12 ml), followed by the dropwise addition of triethylamine (1.4 ml). The mixture was stirred at room temperature for 16 h and then poured into water. After filtration, the precipitate was collected as a yellow solid. The impure product was dissolved in 95% EtOH at room temperature. Colourless monoclinic crystals suitable for X-ray analysis (m.p. 470 K, 87.6% yield) grew over a period of one week when the solution was exposed to the air. CH&N elemental analysis. Calc. for C8H7.5Br3N2O3.25: C 22.70, H 1.79, N 6.62%; found: C 22.65, H 1.83, N 6.68%.
All non-H atoms were refined with anisotropic displacement parameters. All H atoms except the H(W) were positioned geometrically [C—H = 0.97Å for CH2, 0.96Å for CH3, and N—H = 0.86 Å] and refined using a riding model, with Uiso = 1.2Ueq (1.5Ueq for the methyl group) of the parent atom. The H atoms attached to water O atoms in the difference Fourier maps were constrained to their parent O atoms with distance of O—H = 0.8498, and with Uiso = 1.5Ueq.
Pyrrole derivatives are well known in many marine organisms (Faulkner, 2002), some show important bioactivities, such as antitumor activity (Banwell et al., 2006) and protein kinase inhibiting activity (Sosa et al., 2002). This is the reason why they have attracted our interest. This study follows our previous studies on 3-[(3,4,5-Tribromo-1H-pyrrol-2-ylcarbonyl)amino]propanoic acid (Zeng et al., 2006) and 3-Bromo-1-methyl-6,7-dihydropyrrolo[2,3-c]azepine-4,8(1H,5H)-dione (Zeng, 2006).
In the crystal structure, there are 8 molecules of Methyl [(3,4,5-tribromo-1H-pyrrole-2-carbonyl)amino]acetate and 2 crystal water molecules in each unit cell. Molecules of the acetate are linked through N—H···O H-bonds (Table 1) to form centrosymmetric dimers (Fig. 2) of graph-set motif R22(10) (Bernstein et al., 1995). These dimers are connected by O—H(W)···O and N—H···O(W) H-bond interactions, generating the three-dimensional network (Fig. 3). Bond lengths and angles are unexceptional.
For related literature, see: Banwell et al. (2006); Bernstein et al. (1995); Faulkner (2002); Sosa et al. (2002); Zeng (2006); Zeng, Li, Li & Liu (2006).
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.
C8H7Br3N2O3·0.25H2O | F(000) = 1604 |
Mr = 423.39 | Dx = 2.287 Mg m−3 |
Monoclinic, P2/n | Melting point: 470 K |
Hall symbol: -P 2yac | Mo Kα radiation, λ = 0.71073 Å |
a = 15.9656 (19) Å | Cell parameters from 2696 reflections |
b = 9.7566 (12) Å | θ = 2.6–22.7° |
c = 16.1805 (19) Å | µ = 9.84 mm−1 |
β = 102.625 (2)° | T = 293 K |
V = 2459.5 (5) Å3 | Prism, colourless |
Z = 8 | 0.41 × 0.29 × 0.24 mm |
Bruker SMART 1K CCD area-detector diffractometer | 4828 independent reflections |
Radiation source: fine-focus sealed tube | 2608 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.076 |
φ and ω scans | θmax = 26.0°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −19→19 |
Tmin = 0.107, Tmax = 0.201 | k = −12→11 |
14610 measured reflections | l = −19→17 |
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)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.099 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0272P)2 + 4.7343P] where P = (Fo2 + 2Fc2)/3 |
4828 reflections | (Δ/σ)max < 0.001 |
294 parameters | Δρmax = 0.76 e Å−3 |
0 restraints | Δρmin = −0.73 e Å−3 |
C8H7Br3N2O3·0.25H2O | V = 2459.5 (5) Å3 |
Mr = 423.39 | Z = 8 |
Monoclinic, P2/n | Mo Kα radiation |
a = 15.9656 (19) Å | µ = 9.84 mm−1 |
b = 9.7566 (12) Å | T = 293 K |
c = 16.1805 (19) Å | 0.41 × 0.29 × 0.24 mm |
β = 102.625 (2)° |
Bruker SMART 1K CCD area-detector diffractometer | 4828 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2608 reflections with I > 2σ(I) |
Tmin = 0.107, Tmax = 0.201 | Rint = 0.076 |
14610 measured reflections |
R[F2 > 2σ(F2)] = 0.043 | 0 restraints |
wR(F2) = 0.099 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.76 e Å−3 |
4828 reflections | Δρmin = −0.73 e Å−3 |
294 parameters |
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 | ||
Br6 | 0.28459 (5) | 0.85330 (8) | 0.06071 (5) | 0.0418 (2) | |
Br4 | 0.14598 (5) | 0.44478 (9) | −0.19238 (5) | 0.0432 (2) | |
Br3 | 0.23755 (5) | 0.37740 (9) | 0.37613 (5) | 0.0495 (3) | |
Br5 | 0.32222 (5) | 0.68636 (9) | −0.12494 (5) | 0.0496 (3) | |
Br1 | 0.32381 (6) | 0.02225 (10) | 0.66869 (5) | 0.0600 (3) | |
Br2 | 0.16429 (6) | 0.26370 (10) | 0.55774 (7) | 0.0649 (3) | |
O6 | 0.0297 (3) | 0.6921 (5) | 0.3266 (3) | 0.0418 (13) | |
N1 | 0.3844 (4) | 0.0974 (6) | 0.5250 (4) | 0.0356 (16) | |
H1 | 0.4275 | 0.0429 | 0.5392 | 0.043* | |
C9 | 0.1664 (5) | 0.5607 (7) | −0.0988 (4) | 0.0316 (18) | |
N3 | 0.1121 (4) | 0.5678 (6) | −0.0457 (3) | 0.0328 (15) | |
H3 | 0.0665 | 0.5191 | −0.0499 | 0.039* | |
N2 | 0.4197 (4) | 0.2645 (6) | 0.3347 (4) | 0.0416 (17) | |
H2 | 0.3780 | 0.3223 | 0.3267 | 0.050* | |
O4 | 0.0220 (3) | 0.6163 (6) | 0.0733 (3) | 0.0484 (15) | |
C13 | 0.0894 (5) | 0.6823 (8) | 0.0805 (5) | 0.0301 (17) | |
C5 | 0.4292 (5) | 0.1736 (8) | 0.3990 (4) | 0.0361 (19) | |
O2 | 0.3963 (3) | 0.0869 (6) | 0.1948 (3) | 0.0492 (15) | |
C4 | 0.3680 (5) | 0.1792 (7) | 0.4544 (4) | 0.0291 (17) | |
O1 | 0.4869 (3) | 0.0887 (6) | 0.4100 (3) | 0.0503 (15) | |
C12 | 0.1402 (4) | 0.6641 (7) | 0.0160 (4) | 0.0285 (17) | |
O5 | 0.1188 (4) | 0.5676 (6) | 0.2663 (3) | 0.0551 (16) | |
O3 | 0.5235 (3) | 0.1515 (5) | 0.1720 (3) | 0.0519 (16) | |
C15 | 0.0769 (5) | 0.6658 (9) | 0.2688 (4) | 0.0358 (19) | |
C2 | 0.2633 (5) | 0.2076 (8) | 0.5261 (5) | 0.038 (2) | |
C11 | 0.2156 (4) | 0.7166 (7) | −0.0008 (4) | 0.0285 (17) | |
N4 | 0.1166 (4) | 0.7679 (6) | 0.1437 (4) | 0.0346 (15) | |
H4 | 0.1635 | 0.8131 | 0.1469 | 0.041* | |
C7 | 0.4587 (5) | 0.1569 (8) | 0.2114 (5) | 0.0325 (19) | |
C1 | 0.3226 (5) | 0.1157 (8) | 0.5684 (5) | 0.040 (2) | |
C10 | 0.2308 (4) | 0.6520 (7) | −0.0732 (4) | 0.0320 (18) | |
C16 | 0.0345 (6) | 0.5903 (9) | 0.3918 (5) | 0.060 (3) | |
H16A | −0.0080 | 0.5208 | 0.3729 | 0.089* | |
H16B | 0.0241 | 0.6327 | 0.4422 | 0.089* | |
H16C | 0.0905 | 0.5494 | 0.4039 | 0.089* | |
C3 | 0.2933 (5) | 0.2478 (7) | 0.4538 (5) | 0.0325 (18) | |
C8 | 0.5159 (6) | 0.0477 (9) | 0.1066 (5) | 0.066 (3) | |
H8A | 0.5081 | −0.0404 | 0.1303 | 0.100* | |
H8B | 0.5671 | 0.0468 | 0.0847 | 0.100* | |
H8C | 0.4674 | 0.0680 | 0.0617 | 0.100* | |
C14 | 0.0669 (5) | 0.7852 (7) | 0.2076 (4) | 0.0358 (19) | |
H14A | 0.0068 | 0.7949 | 0.1802 | 0.043* | |
H14B | 0.0848 | 0.8687 | 0.2390 | 0.043* | |
C6 | 0.4787 (5) | 0.2648 (8) | 0.2798 (5) | 0.040 (2) | |
H6A | 0.5362 | 0.2496 | 0.3133 | 0.048* | |
H6B | 0.4777 | 0.3543 | 0.2535 | 0.048* | |
O7 | 0.2500 | 0.9820 (8) | 0.2500 | 0.059 (2)* | |
H7 | 0.2933 | 1.0136 | 0.2337 | 0.37 (11)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br6 | 0.0355 (5) | 0.0446 (5) | 0.0444 (5) | −0.0109 (4) | 0.0070 (4) | −0.0039 (4) |
Br4 | 0.0459 (5) | 0.0500 (6) | 0.0341 (4) | −0.0044 (4) | 0.0096 (4) | −0.0073 (4) |
Br3 | 0.0435 (5) | 0.0444 (5) | 0.0548 (6) | 0.0136 (4) | −0.0017 (4) | −0.0009 (4) |
Br5 | 0.0408 (5) | 0.0637 (6) | 0.0507 (5) | −0.0116 (5) | 0.0236 (4) | −0.0056 (5) |
Br1 | 0.0650 (6) | 0.0739 (7) | 0.0470 (5) | 0.0008 (5) | 0.0255 (5) | 0.0096 (5) |
Br2 | 0.0386 (5) | 0.0773 (7) | 0.0843 (7) | 0.0076 (5) | 0.0258 (5) | −0.0145 (6) |
O6 | 0.036 (3) | 0.052 (4) | 0.042 (3) | 0.004 (3) | 0.018 (3) | 0.000 (3) |
N1 | 0.030 (4) | 0.042 (4) | 0.033 (4) | 0.015 (3) | 0.002 (3) | 0.006 (3) |
C9 | 0.039 (5) | 0.030 (5) | 0.028 (4) | 0.004 (4) | 0.013 (4) | 0.001 (3) |
N3 | 0.026 (3) | 0.036 (4) | 0.036 (4) | −0.007 (3) | 0.007 (3) | 0.003 (3) |
N2 | 0.046 (4) | 0.041 (4) | 0.042 (4) | 0.014 (3) | 0.018 (3) | 0.003 (3) |
O4 | 0.036 (3) | 0.063 (4) | 0.052 (3) | −0.021 (3) | 0.021 (3) | −0.019 (3) |
C13 | 0.023 (4) | 0.033 (5) | 0.036 (4) | 0.001 (4) | 0.011 (4) | 0.000 (4) |
C5 | 0.041 (5) | 0.040 (5) | 0.027 (4) | −0.001 (4) | 0.007 (4) | −0.002 (4) |
O2 | 0.045 (4) | 0.043 (4) | 0.063 (4) | −0.011 (3) | 0.020 (3) | −0.002 (3) |
C4 | 0.033 (4) | 0.023 (4) | 0.030 (4) | 0.004 (4) | 0.004 (4) | −0.003 (3) |
O1 | 0.042 (3) | 0.061 (4) | 0.055 (4) | 0.030 (3) | 0.026 (3) | 0.018 (3) |
C12 | 0.023 (4) | 0.031 (5) | 0.029 (4) | −0.002 (3) | 0.001 (3) | 0.002 (4) |
O5 | 0.065 (4) | 0.052 (4) | 0.052 (4) | 0.027 (3) | 0.020 (3) | 0.007 (3) |
O3 | 0.051 (4) | 0.057 (4) | 0.056 (4) | −0.021 (3) | 0.029 (3) | −0.019 (3) |
C15 | 0.032 (5) | 0.049 (6) | 0.027 (4) | −0.001 (4) | 0.008 (4) | −0.006 (4) |
C2 | 0.037 (5) | 0.034 (5) | 0.042 (5) | 0.001 (4) | 0.010 (4) | −0.021 (4) |
C11 | 0.029 (4) | 0.031 (4) | 0.025 (4) | −0.010 (4) | 0.005 (3) | 0.003 (3) |
N4 | 0.034 (4) | 0.036 (4) | 0.035 (4) | −0.014 (3) | 0.011 (3) | −0.013 (3) |
C7 | 0.034 (5) | 0.031 (5) | 0.034 (5) | 0.003 (4) | 0.012 (4) | 0.010 (4) |
C1 | 0.037 (5) | 0.047 (5) | 0.039 (5) | 0.001 (4) | 0.017 (4) | −0.007 (4) |
C10 | 0.029 (4) | 0.040 (5) | 0.031 (4) | −0.005 (4) | 0.014 (4) | −0.003 (4) |
C16 | 0.066 (6) | 0.081 (7) | 0.038 (5) | −0.008 (5) | 0.024 (5) | 0.005 (5) |
C3 | 0.029 (4) | 0.025 (4) | 0.041 (5) | 0.005 (4) | 0.002 (4) | −0.007 (4) |
C8 | 0.067 (6) | 0.084 (7) | 0.057 (6) | −0.020 (6) | 0.033 (5) | −0.033 (5) |
C14 | 0.040 (5) | 0.037 (5) | 0.033 (4) | 0.002 (4) | 0.013 (4) | −0.011 (4) |
C6 | 0.047 (5) | 0.038 (5) | 0.038 (5) | −0.002 (4) | 0.017 (4) | 0.004 (4) |
Br6—C11 | 1.872 (7) | C4—C3 | 1.367 (9) |
Br4—C9 | 1.861 (7) | C12—C11 | 1.388 (9) |
Br3—C3 | 1.866 (7) | O5—C15 | 1.174 (8) |
Br5—C10 | 1.865 (7) | O3—C7 | 1.331 (8) |
Br1—C1 | 1.857 (8) | O3—C8 | 1.450 (8) |
Br2—C2 | 1.847 (7) | C15—C14 | 1.514 (10) |
O6—C15 | 1.348 (8) | C2—C1 | 1.373 (10) |
O6—C16 | 1.439 (9) | C2—C3 | 1.413 (10) |
N1—C1 | 1.342 (8) | C11—C10 | 1.398 (9) |
N1—C4 | 1.371 (8) | N4—C14 | 1.444 (8) |
N1—H1 | 0.8600 | N4—H4 | 0.8600 |
C9—N3 | 1.349 (8) | C7—C6 | 1.511 (10) |
C9—C10 | 1.355 (9) | C16—H16A | 0.9600 |
N3—C12 | 1.373 (8) | C16—H16B | 0.9600 |
N3—H3 | 0.8600 | C16—H16C | 0.9600 |
N2—C5 | 1.350 (9) | C8—H8A | 0.9600 |
N2—C6 | 1.429 (8) | C8—H8B | 0.9600 |
N2—H2 | 0.8600 | C8—H8C | 0.9600 |
O4—C13 | 1.237 (8) | C14—H14A | 0.9700 |
C13—N4 | 1.319 (8) | C14—H14B | 0.9700 |
C13—C12 | 1.466 (9) | C6—H6A | 0.9700 |
C5—O1 | 1.223 (8) | C6—H6B | 0.9700 |
C5—C4 | 1.463 (9) | O7—H7 | 0.8498 |
O2—C7 | 1.189 (8) | ||
C15—O6—C16 | 115.5 (6) | C14—N4—H4 | 120.4 |
C1—N1—C4 | 109.3 (6) | O2—C7—O3 | 124.8 (7) |
C1—N1—H1 | 125.3 | O2—C7—C6 | 126.7 (7) |
C4—N1—H1 | 125.3 | O3—C7—C6 | 108.5 (6) |
N3—C9—C10 | 108.8 (6) | N1—C1—C2 | 109.4 (7) |
N3—C9—Br4 | 121.8 (6) | N1—C1—Br1 | 121.6 (6) |
C10—C9—Br4 | 129.4 (5) | C2—C1—Br1 | 129.1 (6) |
C9—N3—C12 | 110.2 (6) | C9—C10—C11 | 107.0 (6) |
C9—N3—H3 | 124.9 | C9—C10—Br5 | 126.7 (5) |
C12—N3—H3 | 124.9 | C11—C10—Br5 | 126.3 (6) |
C5—N2—C6 | 120.1 (6) | O6—C16—H16A | 109.5 |
C5—N2—H2 | 119.9 | O6—C16—H16B | 109.5 |
C6—N2—H2 | 119.9 | H16A—C16—H16B | 109.5 |
O4—C13—N4 | 122.4 (7) | O6—C16—H16C | 109.5 |
O4—C13—C12 | 118.4 (7) | H16A—C16—H16C | 109.5 |
N4—C13—C12 | 119.3 (6) | H16B—C16—H16C | 109.5 |
O1—C5—N2 | 120.7 (7) | C4—C3—C2 | 108.2 (7) |
O1—C5—C4 | 121.2 (7) | C4—C3—Br3 | 128.5 (6) |
N2—C5—C4 | 118.0 (7) | C2—C3—Br3 | 123.2 (6) |
C3—C4—N1 | 107.3 (6) | O3—C8—H8A | 109.5 |
C3—C4—C5 | 135.5 (7) | O3—C8—H8B | 109.5 |
N1—C4—C5 | 117.2 (6) | H8A—C8—H8B | 109.5 |
N3—C12—C11 | 105.6 (6) | O3—C8—H8C | 109.5 |
N3—C12—C13 | 117.2 (6) | H8A—C8—H8C | 109.5 |
C11—C12—C13 | 137.1 (7) | H8B—C8—H8C | 109.5 |
C7—O3—C8 | 115.3 (6) | N4—C14—C15 | 112.5 (6) |
O5—C15—O6 | 126.0 (7) | N4—C14—H14A | 109.1 |
O5—C15—C14 | 125.8 (7) | C15—C14—H14A | 109.1 |
O6—C15—C14 | 108.2 (7) | N4—C14—H14B | 109.1 |
C1—C2—C3 | 105.8 (6) | C15—C14—H14B | 109.1 |
C1—C2—Br2 | 126.4 (6) | H14A—C14—H14B | 107.8 |
C3—C2—Br2 | 127.8 (6) | N2—C6—C7 | 113.0 (6) |
C12—C11—C10 | 108.4 (6) | N2—C6—H6A | 109.0 |
C12—C11—Br6 | 126.4 (5) | C7—C6—H6A | 109.0 |
C10—C11—Br6 | 125.2 (5) | N2—C6—H6B | 109.0 |
C13—N4—C14 | 119.3 (6) | C7—C6—H6B | 109.0 |
C13—N4—H4 | 120.4 | H6A—C6—H6B | 107.8 |
C10—C9—N3—C12 | −0.1 (8) | C4—N1—C1—Br1 | −179.5 (5) |
Br4—C9—N3—C12 | −177.8 (5) | C3—C2—C1—N1 | −1.2 (9) |
C6—N2—C5—O1 | −1.7 (11) | Br2—C2—C1—N1 | 178.1 (5) |
C6—N2—C5—C4 | 178.8 (6) | C3—C2—C1—Br1 | 179.9 (6) |
C1—N1—C4—C3 | −1.0 (8) | Br2—C2—C1—Br1 | −0.8 (11) |
C1—N1—C4—C5 | 179.7 (6) | N3—C9—C10—C11 | 0.6 (8) |
O1—C5—C4—C3 | −171.0 (8) | Br4—C9—C10—C11 | 178.1 (5) |
N2—C5—C4—C3 | 8.5 (13) | N3—C9—C10—Br5 | −179.0 (5) |
O1—C5—C4—N1 | 7.9 (11) | Br4—C9—C10—Br5 | −1.5 (11) |
N2—C5—C4—N1 | −172.6 (6) | C12—C11—C10—C9 | −0.9 (8) |
C9—N3—C12—C11 | −0.5 (8) | Br6—C11—C10—C9 | −179.6 (5) |
C9—N3—C12—C13 | −178.5 (6) | C12—C11—C10—Br5 | 178.7 (5) |
O4—C13—C12—N3 | −4.0 (10) | Br6—C11—C10—Br5 | 0.0 (10) |
N4—C13—C12—N3 | 176.1 (6) | N1—C4—C3—C2 | 0.3 (8) |
O4—C13—C12—C11 | 178.8 (8) | C5—C4—C3—C2 | 179.3 (8) |
N4—C13—C12—C11 | −1.1 (13) | N1—C4—C3—Br3 | 178.5 (5) |
C16—O6—C15—O5 | 1.9 (11) | C5—C4—C3—Br3 | −2.5 (13) |
C16—O6—C15—C14 | −177.9 (6) | C1—C2—C3—C4 | 0.5 (8) |
N3—C12—C11—C10 | 0.8 (8) | Br2—C2—C3—C4 | −178.8 (5) |
C13—C12—C11—C10 | 178.2 (8) | C1—C2—C3—Br3 | −177.8 (5) |
N3—C12—C11—Br6 | 179.5 (5) | Br2—C2—C3—Br3 | 2.9 (10) |
C13—C12—C11—Br6 | −3.1 (13) | C13—N4—C14—C15 | 75.8 (8) |
O4—C13—N4—C14 | 0.5 (11) | O5—C15—C14—N4 | −0.9 (11) |
C12—C13—N4—C14 | −179.6 (6) | O6—C15—C14—N4 | 178.9 (6) |
C8—O3—C7—O2 | −2.3 (11) | C5—N2—C6—C7 | 81.4 (9) |
C8—O3—C7—C6 | 177.3 (6) | O2—C7—C6—N2 | 8.7 (11) |
C4—N1—C1—C2 | 1.4 (9) | O3—C7—C6—N2 | −170.9 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4···O7 | 0.86 | 2.53 | 3.202 (8) | 136 |
O7—H7···O2i | 0.85 | 2.02 | 2.866 (6) | 180 |
N3—H3···O4ii | 0.86 | 1.91 | 2.756 (8) | 167 |
N1—H1···O1iii | 0.86 | 1.92 | 2.772 (8) | 168 |
Symmetry codes: (i) x, y+1, z; (ii) −x, −y+1, −z; (iii) −x+1, −y, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C8H7Br3N2O3·0.25H2O |
Mr | 423.39 |
Crystal system, space group | Monoclinic, P2/n |
Temperature (K) | 293 |
a, b, c (Å) | 15.9656 (19), 9.7566 (12), 16.1805 (19) |
β (°) | 102.625 (2) |
V (Å3) | 2459.5 (5) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 9.84 |
Crystal size (mm) | 0.41 × 0.29 × 0.24 |
Data collection | |
Diffractometer | Bruker SMART 1K CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.107, 0.201 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14610, 4828, 2608 |
Rint | 0.076 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.043, 0.099, 1.01 |
No. of reflections | 4828 |
No. of parameters | 294 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.76, −0.73 |
Computer programs: SMART (Bruker,1999), SAINT-Plus (Bruker, 1999), SAINT-Plus, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4···O7 | 0.86 | 2.53 | 3.202 (8) | 135.7 |
O7—H7···O2i | 0.85 | 2.02 | 2.866 (6) | 179.5 |
N3—H3···O4ii | 0.86 | 1.91 | 2.756 (8) | 167.1 |
N1—H1···O1iii | 0.86 | 1.92 | 2.772 (8) | 168.2 |
Symmetry codes: (i) x, y+1, z; (ii) −x, −y+1, −z; (iii) −x+1, −y, −z+1. |
Pyrrole derivatives are well known in many marine organisms (Faulkner, 2002), some show important bioactivities, such as antitumor activity (Banwell et al., 2006) and protein kinase inhibiting activity (Sosa et al., 2002). This is the reason why they have attracted our interest. This study follows our previous studies on 3-[(3,4,5-Tribromo-1H-pyrrol-2-ylcarbonyl)amino]propanoic acid (Zeng et al., 2006) and 3-Bromo-1-methyl-6,7-dihydropyrrolo[2,3-c]azepine-4,8(1H,5H)-dione (Zeng, 2006).
In the crystal structure, there are 8 molecules of Methyl [(3,4,5-tribromo-1H-pyrrole-2-carbonyl)amino]acetate and 2 crystal water molecules in each unit cell. Molecules of the acetate are linked through N—H···O H-bonds (Table 1) to form centrosymmetric dimers (Fig. 2) of graph-set motif R22(10) (Bernstein et al., 1995). These dimers are connected by O—H(W)···O and N—H···O(W) H-bond interactions, generating the three-dimensional network (Fig. 3). Bond lengths and angles are unexceptional.