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
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.010 Å Some non-H atoms missing
- R factor = 0.043
- wR factor = 0.099
- Data-to-parameter ratio = 16.4
checkCIF/PLATON results
No syntax errors found
Alert level A ABSMU01_ALERT_1_A The ratio of given/expected absorption coefficient lies outside the range 0.90 <> 1.10 Calculated value of mu = 4.934 Value of mu given = 9.837 CHEMW01_ALERT_1_A The ratio of given/expected molecular weight as calculated from the _chemical_formula_sum lies outside the range 0.90 <> 1.10 Calculated formula weight = 263.5090 Formula weight given = 423.3900
Alert level B PLAT431_ALERT_2_B Short Inter HL..A Contact Br3 .. O5 .. 2.95 Ang.
Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR) is > 1.10 Tmin and Tmax reported: 0.107 0.201 Tmin and Tmax expected: 0.044 0.094 RR = 1.142 Please check that your absorption correction is appropriate. CHEMW01_ALERT_1_C The difference between the given and expected weight for compound is greater 1 mass unit. Check that all hydrogen atoms have been taken into account. PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.25 Ratio PLAT060_ALERT_3_C Ratio Tmax/Tmin (Exp-to-Rep) (too) Large ....... 1.10 PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.47 PLAT128_ALERT_4_C Non-standard setting of Space group P2/c .... P2/n PLAT202_ALERT_3_C Isotropic non-H Atoms in Anion/Solvent ......... 1 PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 10 PLAT431_ALERT_2_C Short Inter HL..A Contact Br5 .. O3 .. 3.16 Ang.
Alert level G FORMU01_ALERT_1_G There is a discrepancy between the atom counts in the _chemical_formula_sum and _chemical_formula_moiety. This is usually due to the moiety formula being in the wrong format. Atom count from _chemical_formula_sum: C8 H7.5 Br1.5 N1 O1.625 Atom count from _chemical_formula_moiety:C8 H7.5 Br3 N2 O3.25 FORMU01_ALERT_2_G There is a discrepancy between the atom counts in the _chemical_formula_sum and the formula from the _atom_site* data. Atom count from _chemical_formula_sum:C8 H7.5 Br1.5 N1 O1.625 Atom count from the _atom_site data: C8 H7.5 Br3 N2 O3.25 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 0.469 Tmax scaled 0.094 Tmin scaled 0.050 CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected. CELLZ01_ALERT_1_G ALERT: Large difference may be due to a symmetry error - see SYMMG tests From the CIF: _cell_formula_units_Z 8 From the CIF: _chemical_formula_sum C8 H7.5 Br1.5 N1 O1.625 TEST: Compare cell contents of formula and atom_site data atom Z*formula cif sites diff C 64.00 64.00 0.00 H 60.00 60.00 0.00 Br 12.00 24.00 -12.00 N 8.00 16.00 -8.00 O 13.00 26.00 -13.00 PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
2 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 11 ALERT level C = Check and explain 7 ALERT level G = General alerts; check 11 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 5 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
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).
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. |
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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.