In a dehydroamino acid with a C=C bond between the α- and β-C atoms, the amino acid residues are linked trans to each other and there are no strong intramolecular hydrogen bonds. The torsion angles indicate a non-helical conformation of the molecule.
Keywords: crystal structure, β-bromodehydroalanine, dehydroamino acid, non-helical conformation, hydrogen bonding
Abstract
The title compound, C11H17BrN2O5, is a dehydroamino acid with a C=C bond between the α- and β-C atoms. The amino acid residues are linked trans to each other and there are no strong intramolecular hydrogen bonds. The torsion angles indicate a non-helical conformation of the molecule. The dipeptide folding is influenced by an intermolecular N—H⋯O hydrogen bond and also minimizes steric repulsion. In the crystal, molecules are linked by strong N—H⋯O hydrogen bonds, generating (001) sheets. The sheets are linked by weak C—H⋯O and C—H⋯Br bonds and short Br⋯Br [3.4149 (3) Å] interactions.
Chemical context
Dehydroamino acids are analogues of amino acids characterized by the presence of an unsaturated doubled bound between the α- and β-carbon atoms in their structure. These compounds were found to be components of natural products (Bonauer et al., 2006 ▶), with lantibiotics being especially important since they are an important class of natural bacteriocins produced by Gram-positive bacteria (Willey & van der Donk, 2007 ▶). The development of synthetic methods for the preparation of dehydropeptides allows researchers to search for their practical applications and to use them as substrates for the production of peptidomimetics. One of the interesting classes of such mimetics are β-bromo-dehydroamino acids and their derivatives, which are usually obtained by radical halogenation of dehydroamino acids using N-bromosuccinimide (NBS). This reaction proceeds in two steps, namely by halogenation of dehydroamino acids, which gives α-bromo-imines, followed by tautomerization to the desired products upon treatment with an amine (Coleman & Carpenter, 1993 ▶; Zhang et al., 2002 ▶). β-Bromo-dehydroamino acid derivatives are useful substrates in coupling reactions with alkynes (Singh et al., 2003 ▶) or organoboranes (Collier et al. 2002 ▶; Zhang et al., 2002 ▶). Further asymmetric hydrogenation of their double bound allows non-proteinogenic α-amino acids and their derivatives to be obtained. Another important reaction of β-bromo-α,β-dehydroamino acid derivatives in drug research is their coupling cyclization in which oxazole derivatives are produced (Liu et al., 2014 ▶).
Structural commentary
The molecular structure of the title compound, (I), is shown in Fig. 1 ▶. The amino acids in the compound are linked trans to each other. The ω2 angle (C9—C10—N12—C13) is 175.79 (16)°, while ω3 (O5—C6—N8—C9) is 176.12 (15)°. There are no strong intramolecular hydrogen bonds. The values of the ϕ2,3 and ψ2,3 angles corresponds to a non-helical conformation (Venkatachalam, 1968 ▶). The dipeptide folds accordingly to the intermolecular N—H⋯O-type hydrogen bonds. The β-bromo-dehydroalanine moiety shows typical geometrical tendencies. The C10—N12 bond is longer [1.366 (2) Å] than a typical bond in alanine, while the N12—C13 bond is shorter [1.406 (2) Å]. This effect is common for other dehydro-residues (Ajó et al., 1979 ▶; Pieroni et al. 1975 ▶; Rzeszotarska et al., 2002 ▶; Jain & Chauhan, 1996 ▶). This indicates conjugation between the side chain of dehydroalanine and the peptide bond. The torsion angles around the Br(H)C=C grouping are −0.9 (3) and −174.28 (13)° (N12—C13—C14—Br15 and C16—C13—C14—Br15, respectively), meaning the stereochemistry about the bond is especially planar. This is consistent with the nature of an sp 2-hybridized carbon on C13. The valance angles around the dehydroalanine group show some unusual values, especially N12—C13—C14 [124.27 (18)°], which may correspond to the presence of the bromine atom in the structure. The other angles are normal, as the backbone of the molecule is folded to minimize steric repulsion. The Boc group features two short intramolecular C—H⋯O contacts
Figure 1.
The molecular structure of Boc–Gly–(β-Br)(Z)ΔAla–OMe along with selected intramolecular hydrogen bonds (dashed lines), drawn with 50% displacement ellipsoids.
Supramolecular features
In the crystal, molecules form two strong twin N—H⋯O (N8—H8A⋯O17i and N12—H12A⋯O7ii) and one weak accompanying C9—H9A⋯O11i hydrogen bonds (Fig. 1 ▶ and Table 1 ▶), forming infinite sheets in the (001) plane [symmetry codes: (i) −x + 2, −y, −z + 1 and (ii) −x + 3, −y, −z + 1]. The sheets are connected to each other by weak C14—H14A⋯O11iii and C19—H19B⋯Br15iii hydrogen bonds and one Br⋯Briv [3.4149 (3) Å] halogen bond (Fig. 2 ▶) of type I (Mukherjee & Desiraju, 2014 ▶) [symmetry codes: (iii) −x + 2, −y + 1, −z + 1; (iv) −x + 3, −y + 1, −z + 1].
Table 1. Hydrogen-bond geometry (, ).
| DHA | DH | HA | D A | DHA |
|---|---|---|---|---|
| C2H2AO7 | 0.96 | 2.51 | 3.058(2) | 116 |
| C3H3AO7 | 0.96 | 2.44 | 3.007(3) | 117 |
| N8H8AO17i | 0.86 | 2.19 | 3.018(2) | 162 |
| C9H9AO11i | 0.97 | 2.61 | 3.255(2) | 124 |
| N12H12AO7ii | 0.86 | 2.04 | 2.901(2) | 174 |
| C14H14AO11iii | 0.93 | 2.43 | 3.095(2) | 129 |
| C19H19BBr15iii | 0.96 | 3.14 | 3.668(3) | 117 |
Symmetry codes: (i) 
; (ii) 
; (iii) 
.
Figure 2.
A packing diagram of (I), viewed along the b axis, showing the intermolecular hydrogen-bonding scheme (dashed lines).
Synthesis and crystallization
Boc–Gly–ΔAla and its methyl ester were prepared according to the methodology described by Makowski et al. (1985 ▶) and Cossec et al. (2008 ▶). The β-bromo-vinyl derivative was obtained based on a procedure described previously (Bull et al., 2007 ▶). For this purpose 0.129 g (0.5 mM) of Boc–Gly–ΔAla–OMe was dissolved in 2.5 ml of dichloromethane and cooled to 193 K. Then, bromine 0.027 ml (0.5 mM) was added. The solution was stirred over 10 minutes followed by addition of triethylamine 0.210 ml (1.5 mM). After 15 minutes, the mixture was quenched with 20 ml of saturated aqueous NaHCO3 and warmed to room temperature. The product was extracted by dichloromethane (3 × 15 ml). The organic layer was washed with brine (3 × 10 ml) and dried over anhydrous Na2SO4. Evaporation of the solvent at reduced pressure gave 0.119 g (0.35 mM) of crude product (70% yield). Recrystallization was performed from mixtures of diethyl ether/ethyl acetate(2:1)/hexane solvents, yielding irregular colourless crystals. It is worth noting that in the case of our study, the formation of only the Z isomer was observed while in the preceding paper, the bromination of dehydroalanine-containing compound gave the E isomer. 1H NMR (400 MHz, DMSO) δ 1.38 (s, (s, 9H, C—H3 t-Boc), 3.67 (s, 3H, O—CH3), 3.69 (d, J = 6.2 Hz, 2H, C—H2 Gly), 7.05 (t, J = 6.2 Hz, 1H, N—HGly), 7.30 (s, 1H, C=CHBr), 9.63 (s, 1H, N—Hβ-Br–ΔAla). 13C NMR (101 MHz, DMSO) δ 28.21, 42.79, 52.54, 78.12, 113.26, 132.88, 155.80, 162.63, 168.80. Melting point = 386–388 K.
Refinement
Crystal data, data collection and structure refinement details are summarized in Table 2 ▶. All H atoms were positioned geometrically and treated as riding on their parent C or N atoms: for methyl groups, C—H = 0.96 Å and U iso (H) = 1.5U eq(C); for N atoms, N—H = 0.86 Å and U iso (H) = 1.2U eq(C); for secondary C atoms, C—H = 0.97 Å and U iso (H) = 1.2U eq(C), with no refinement of their parameters.
Table 2. Experimental details.
| Crystal data | |
| Chemical formula | C11H17BrN2O5 |
| M r | 337.17 |
| Crystal system, space group | Triclinic, P
|
| Temperature (K) | 100 |
| a, b, c () | 9.0431(4), 9.3160(4), 9.7540(4) |
| , , () | 83.381(3), 75.420(4), 64.863(4) |
| V (3) | 719.92(6) |
| Z | 2 |
| Radiation type | Mo K |
| (mm1) | 2.87 |
| Crystal size (mm) | 0.30 0.25 0.20 |
| Data collection | |
| Diffractometer | Oxford Diffraction Xcalibur |
| Absorption correction | Multi-scan (CrysAlis RED; Oxford Diffraction, 2010 ▶) |
| T min, T max | 0.655, 1.000 |
| No. of measured, independent and observed [I > 2(I)] reflections | 4860, 2780, 2490 |
| R int | 0.016 |
| (sin /)max (1) | 0.617 |
| Refinement | |
| R[F 2 > 2(F 2)], wR(F 2), S | 0.024, 0.066, 1.06 |
| No. of reflections | 2780 |
| No. of parameters | 172 |
| H-atom treatment | H-atom parameters constrained |
| max, min (e 3) | 0.53, 0.43 |
Supplementary Material
Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814025677/hb7312sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814025677/hb7312Isup2.hkl
CCDC reference: 1035539
Additional supporting information: crystallographic information; 3D view; checkCIF report
Acknowledgments
This study was supported by the Wrocław Research Centre EIT+ under the project Biotechnologies and advanced medical technologies – BioMed (POIG.01.01.02–02-003/08) financed from the European Regional Development Fund (Operational Programme Innovative Economy, 1.1.2). PL is the recipient of a PhD fellowships from a project funded by the European Social Fund.
supplementary crystallographic information
Crystal data
| C11H17BrN2O5 | Z = 2 |
| Mr = 337.17 | F(000) = 344 |
| Triclinic, P1 | Dx = 1.555 Mg m−3 |
| a = 9.0431 (4) Å | Mo Kα radiation, λ = 0.71073 Å |
| b = 9.3160 (4) Å | Cell parameters from 4860 reflections |
| c = 9.7540 (4) Å | θ = 3.2–26.0° |
| α = 83.381 (3)° | µ = 2.87 mm−1 |
| β = 75.420 (4)° | T = 100 K |
| γ = 64.863 (4)° | Irregular, colourless |
| V = 719.92 (6) Å3 | 0.30 × 0.25 × 0.20 mm |
Data collection
| Oxford Diffraction Xcalibur diffractometer | 2780 independent reflections |
| Radiation source: fine-focus sealed tube | 2490 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.016 |
| Detector resolution: 1024 pixels mm-1 | θmax = 26.0°, θmin = 3.2° |
| ω scan | h = −8→11 |
| Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010) | k = −10→11 |
| Tmin = 0.655, Tmax = 1.000 | l = −12→12 |
| 4860 measured reflections |
Refinement
| Refinement on F2 | 0 restraints |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.024 | H-atom parameters constrained |
| wR(F2) = 0.066 | w = 1/[σ2(Fo2) + (0.0444P)2] where P = (Fo2 + 2Fc2)/3 |
| S = 1.06 | (Δ/σ)max = 0.001 |
| 2780 reflections | Δρmax = 0.53 e Å−3 |
| 172 parameters | Δρmin = −0.43 e Å−3 |
Special details
| Experimental. CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.33.57 (release 26-01-2010 CrysAlis171 .NET) (compiled Jan 26 2010,14:36:55) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. |
| 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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| C1 | 1.2957 (3) | −0.1495 (2) | 0.9892 (2) | 0.0186 (4) | |
| C2 | 1.4783 (3) | −0.2662 (3) | 0.9655 (2) | 0.0248 (5) | |
| H2A | 1.5455 | −0.2243 | 0.8952 | 0.037* | |
| H2B | 1.4904 | −0.3651 | 0.9336 | 0.037* | |
| H2C | 1.5146 | −0.2830 | 1.0527 | 0.037* | |
| C3 | 1.2675 (3) | 0.0136 (3) | 1.0284 (2) | 0.0291 (5) | |
| H3A | 1.3374 | 0.0518 | 0.9572 | 0.044* | |
| H3B | 1.2952 | 0.0083 | 1.1182 | 0.044* | |
| H3C | 1.1520 | 0.0844 | 1.0348 | 0.044* | |
| C4 | 1.1870 (3) | −0.2140 (3) | 1.1000 (2) | 0.0313 (5) | |
| H4A | 1.0720 | −0.1387 | 1.1146 | 0.047* | |
| H4B | 1.2228 | −0.2316 | 1.1875 | 0.047* | |
| H4C | 1.1975 | −0.3122 | 1.0679 | 0.047* | |
| O5 | 1.23184 (17) | −0.14194 (16) | 0.86239 (14) | 0.0186 (3) | |
| C6 | 1.2959 (2) | −0.0915 (2) | 0.7363 (2) | 0.0144 (4) | |
| O7 | 1.40332 (16) | −0.03851 (15) | 0.71486 (14) | 0.0161 (3) | |
| N8 | 1.2267 (2) | −0.10813 (19) | 0.63638 (17) | 0.0155 (3) | |
| H8A | 1.1573 | −0.1522 | 0.6578 | 0.019* | |
| C9 | 1.2670 (2) | −0.0531 (2) | 0.49289 (19) | 0.0149 (4) | |
| H9A | 1.2529 | −0.1157 | 0.4283 | 0.018* | |
| H9B | 1.3835 | −0.0685 | 0.4688 | 0.018* | |
| C10 | 1.1567 (2) | 0.1209 (2) | 0.47430 (19) | 0.0143 (4) | |
| O11 | 1.00831 (16) | 0.18140 (15) | 0.53245 (14) | 0.0179 (3) | |
| N12 | 1.23628 (19) | 0.20273 (18) | 0.38410 (17) | 0.0146 (3) | |
| H12A | 1.3421 | 0.1556 | 0.3484 | 0.017* | |
| C13 | 1.1490 (2) | 0.3623 (2) | 0.34831 (19) | 0.0136 (4) | |
| C14 | 1.1990 (2) | 0.4770 (2) | 0.3536 (2) | 0.0164 (4) | |
| H14A | 1.1341 | 0.5792 | 0.3266 | 0.020* | |
| Br15 | 1.39326 (2) | 0.44202 (2) | 0.41252 (2) | 0.02292 (9) | |
| C16 | 1.0010 (2) | 0.4006 (2) | 0.2866 (2) | 0.0163 (4) | |
| O17 | 0.97138 (18) | 0.30286 (17) | 0.24167 (15) | 0.0210 (3) | |
| O18 | 0.90913 (18) | 0.55685 (16) | 0.28281 (16) | 0.0239 (3) | |
| C19 | 0.7741 (3) | 0.6065 (3) | 0.2098 (3) | 0.0324 (5) | |
| H19A | 0.7155 | 0.7199 | 0.2129 | 0.049* | |
| H19B | 0.6979 | 0.5594 | 0.2552 | 0.049* | |
| H19C | 0.8193 | 0.5731 | 0.1130 | 0.049* |
Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| C1 | 0.0226 (10) | 0.0227 (10) | 0.0121 (9) | −0.0104 (9) | −0.0065 (8) | 0.0034 (8) |
| C2 | 0.0266 (11) | 0.0256 (11) | 0.0202 (11) | −0.0075 (9) | −0.0108 (9) | 0.0066 (9) |
| C3 | 0.0397 (14) | 0.0268 (12) | 0.0204 (11) | −0.0129 (10) | −0.0070 (10) | −0.0014 (9) |
| C4 | 0.0369 (13) | 0.0432 (14) | 0.0172 (11) | −0.0222 (11) | −0.0058 (9) | 0.0088 (10) |
| O5 | 0.0202 (7) | 0.0248 (7) | 0.0141 (7) | −0.0133 (6) | −0.0061 (6) | 0.0077 (6) |
| C6 | 0.0131 (9) | 0.0102 (9) | 0.0158 (10) | −0.0021 (7) | −0.0029 (7) | 0.0040 (7) |
| O7 | 0.0173 (7) | 0.0166 (7) | 0.0174 (7) | −0.0100 (6) | −0.0049 (5) | 0.0028 (5) |
| N8 | 0.0169 (8) | 0.0164 (8) | 0.0167 (8) | −0.0105 (7) | −0.0063 (7) | 0.0074 (7) |
| C9 | 0.0175 (9) | 0.0136 (9) | 0.0136 (9) | −0.0069 (8) | −0.0042 (7) | 0.0038 (7) |
| C10 | 0.0187 (10) | 0.0152 (9) | 0.0126 (9) | −0.0091 (8) | −0.0065 (8) | 0.0017 (7) |
| O11 | 0.0153 (7) | 0.0149 (7) | 0.0198 (7) | −0.0054 (6) | −0.0009 (6) | 0.0035 (5) |
| N12 | 0.0120 (8) | 0.0130 (8) | 0.0169 (8) | −0.0050 (6) | −0.0019 (6) | 0.0034 (6) |
| C13 | 0.0147 (9) | 0.0143 (9) | 0.0115 (9) | −0.0069 (8) | −0.0019 (7) | 0.0031 (7) |
| C14 | 0.0137 (9) | 0.0164 (9) | 0.0191 (10) | −0.0061 (8) | −0.0049 (8) | 0.0021 (8) |
| Br15 | 0.01942 (12) | 0.02164 (12) | 0.03230 (14) | −0.01022 (9) | −0.00996 (9) | −0.00138 (8) |
| C16 | 0.0181 (10) | 0.0171 (10) | 0.0130 (9) | −0.0083 (8) | −0.0032 (8) | 0.0060 (8) |
| O17 | 0.0250 (8) | 0.0209 (7) | 0.0224 (8) | −0.0129 (6) | −0.0093 (6) | 0.0028 (6) |
| O18 | 0.0222 (7) | 0.0168 (7) | 0.0346 (9) | −0.0061 (6) | −0.0164 (6) | 0.0071 (6) |
| C19 | 0.0287 (12) | 0.0290 (12) | 0.0417 (14) | −0.0095 (10) | −0.0229 (11) | 0.0157 (10) |
Geometric parameters (Å, º)
| C1—O5 | 1.474 (2) | C9—C10 | 1.518 (2) |
| C1—C3 | 1.508 (3) | C9—H9A | 0.9700 |
| C1—C2 | 1.517 (3) | C9—H9B | 0.9700 |
| C1—C4 | 1.521 (3) | C10—O11 | 1.220 (2) |
| C2—H2A | 0.9600 | C10—N12 | 1.366 (2) |
| C2—H2B | 0.9600 | N12—C13 | 1.406 (2) |
| C2—H2C | 0.9600 | N12—H12A | 0.8600 |
| C3—H3A | 0.9600 | C13—C14 | 1.335 (3) |
| C3—H3B | 0.9600 | C13—C16 | 1.494 (3) |
| C3—H3C | 0.9600 | C14—Br15 | 1.8715 (19) |
| C4—H4A | 0.9600 | C14—H14A | 0.9300 |
| C4—H4B | 0.9600 | C16—O17 | 1.204 (2) |
| C4—H4C | 0.9600 | C16—O18 | 1.337 (2) |
| O5—C6 | 1.345 (2) | O18—C19 | 1.447 (2) |
| C6—O7 | 1.229 (2) | C19—H19A | 0.9600 |
| C6—N8 | 1.338 (2) | C19—H19B | 0.9600 |
| N8—C9 | 1.446 (2) | C19—H19C | 0.9600 |
| N8—H8A | 0.8600 | ||
| O5—C1—C3 | 110.80 (16) | C9—N8—H8A | 119.5 |
| O5—C1—C2 | 109.75 (16) | N8—C9—C10 | 111.87 (15) |
| C3—C1—C2 | 112.96 (18) | N8—C9—H9A | 109.2 |
| O5—C1—C4 | 101.56 (15) | C10—C9—H9A | 109.2 |
| C3—C1—C4 | 110.90 (18) | N8—C9—H9B | 109.2 |
| C2—C1—C4 | 110.29 (18) | C10—C9—H9B | 109.2 |
| C1—C2—H2A | 109.5 | H9A—C9—H9B | 107.9 |
| C1—C2—H2B | 109.5 | O11—C10—N12 | 122.87 (17) |
| H2A—C2—H2B | 109.5 | O11—C10—C9 | 122.69 (16) |
| C1—C2—H2C | 109.5 | N12—C10—C9 | 114.41 (16) |
| H2A—C2—H2C | 109.5 | C10—N12—C13 | 121.43 (16) |
| H2B—C2—H2C | 109.5 | C10—N12—H12A | 119.3 |
| C1—C3—H3A | 109.5 | C13—N12—H12A | 119.3 |
| C1—C3—H3B | 109.5 | C14—C13—N12 | 124.27 (18) |
| H3A—C3—H3B | 109.5 | C14—C13—C16 | 118.50 (17) |
| C1—C3—H3C | 109.5 | N12—C13—C16 | 116.92 (16) |
| H3A—C3—H3C | 109.5 | C13—C14—Br15 | 123.17 (15) |
| H3B—C3—H3C | 109.5 | C13—C14—H14A | 118.4 |
| C1—C4—H4A | 109.5 | Br15—C14—H14A | 118.4 |
| C1—C4—H4B | 109.5 | O17—C16—O18 | 124.26 (18) |
| H4A—C4—H4B | 109.5 | O17—C16—C13 | 124.08 (18) |
| C1—C4—H4C | 109.5 | O18—C16—C13 | 111.61 (16) |
| H4A—C4—H4C | 109.5 | C16—O18—C19 | 115.57 (16) |
| H4B—C4—H4C | 109.5 | O18—C19—H19A | 109.5 |
| C6—O5—C1 | 121.71 (14) | O18—C19—H19B | 109.5 |
| O7—C6—N8 | 124.52 (17) | H19A—C19—H19B | 109.5 |
| O7—C6—O5 | 125.30 (17) | O18—C19—H19C | 109.5 |
| N8—C6—O5 | 110.18 (16) | H19A—C19—H19C | 109.5 |
| C6—N8—C9 | 120.96 (15) | H19B—C19—H19C | 109.5 |
| C6—N8—H8A | 119.5 | ||
| C3—C1—O5—C6 | 62.8 (2) | C9—C10—N12—C13 | 175.79 (16) |
| C2—C1—O5—C6 | −62.6 (2) | C10—N12—C13—C14 | 130.6 (2) |
| C4—C1—O5—C6 | −179.35 (17) | C10—N12—C13—C16 | −55.9 (2) |
| C1—O5—C6—O7 | −4.7 (3) | N12—C13—C14—Br15 | −0.9 (3) |
| C1—O5—C6—N8 | 174.87 (15) | C16—C13—C14—Br15 | −174.28 (13) |
| O7—C6—N8—C9 | −4.3 (3) | C14—C13—C16—O17 | 159.29 (19) |
| O5—C6—N8—C9 | 176.12 (15) | N12—C13—C16—O17 | −14.6 (3) |
| C6—N8—C9—C10 | −86.1 (2) | C14—C13—C16—O18 | −18.4 (2) |
| N8—C9—C10—O11 | −38.0 (3) | N12—C13—C16—O18 | 167.72 (16) |
| N8—C9—C10—N12 | 143.70 (16) | O17—C16—O18—C19 | −4.6 (3) |
| O11—C10—N12—C13 | −2.5 (3) | C13—C16—O18—C19 | 173.12 (17) |
Hydrogen-bond geometry (Å, º)
| D—H···A | D—H | H···A | D···A | D—H···A |
| C2—H2A···O7 | 0.96 | 2.51 | 3.058 (2) | 116 |
| C3—H3A···O7 | 0.96 | 2.44 | 3.007 (3) | 117 |
| N8—H8A···O17i | 0.86 | 2.19 | 3.018 (2) | 162 |
| C9—H9A···O11i | 0.97 | 2.61 | 3.255 (2) | 124 |
| N12—H12A···O7ii | 0.86 | 2.04 | 2.901 (2) | 174 |
| C14—H14A···O11iii | 0.93 | 2.43 | 3.095 (2) | 129 |
| C19—H19B···Br15iii | 0.96 | 3.14 | 3.668 (3) | 117 |
Symmetry codes: (i) −x+2, −y, −z+1; (ii) −x+3, −y, −z+1; (iii) −x+2, −y+1, −z+1.
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Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Supplementary Materials
Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814025677/hb7312sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814025677/hb7312Isup2.hkl
CCDC reference: 1035539
Additional supporting information: crystallographic information; 3D view; checkCIF report