organic compounds
Dabigatran etexilate tetrahydrate
aState Key Laboratory of Drug Delivery Technology and Pharmacokinetics, Tianjin Centre for New Drug Safety Assessment and Research, Tianjin 300193, People's Republic of China, and bGraduate School, Tianjin University of Traditional Chinese Medicine, Tianjin 300193, People's Republic of China
*Correspondence e-mail: xiupingshen@yahoo.com
In the title compound, C34H41N7O5·4H2O (systematic name: ethyl 3-{[2-({4-[(Z)-amino(hexyloxycarbonylimino)methyl]anilino}methyl)-1-methylbenzimidazole-5-carbonyl]pyridin-2-ylamino}propanoate tetrahydrate), the benzene and pyridine rings form dihedral angles of 5.4 (1) and 43.8 (1)°, respectively, with the benzimidazole mean plane. The terminal butyl group is disordered over two conformations in a 0.756 (10):0.244 (10) ratio. There is an intramolecular N—H⋯O hydrogen bond present. In the crystal, the water molecules are involved in the formation of O—H⋯O, O—H⋯N and N—H⋯O hydrogen bonds, which link the components into layers parallel to the ab plane.
Related literature
For background to the anticoagulant drug dabigatran etexilate, see: Nagarakanti & Ellis (2012); Van Ryn et al. (2010).
Experimental
Crystal data
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Refinement
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Data collection: CrystalClear (Rigaku/MSC, 2009); cell CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.
Supporting information
10.1107/S1600536812046673/cv5357sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812046673/cv5357Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812046673/cv5357Isup3.cml
5.00 g (10 mmol) of ethyl 3-(2-((4-carbamimidoylphenylamino)methyl)-1-methyl-N-(pyridin-2-yl)- 1H-benzo[d]imidazole-5-carboxamido)propanoate was dissolved in 40 ml of THF and 10 ml of water, and 8.29 (60 mmol) of potassium carbonate was added. The mixture was stirred at room temperature for 20 min, followed by dropwise addition of 3.29 g (20 mmol) of n-hexyl chloroformate. The reaction mixture was stirred at room temperature until the reaction completed (typical 4–6 h). The reaction mixture was diluted with 100 ml of dichloromethane, washed with saturated brine, dried over sodium sulfate and evaporated on a rotary evaporator to afford the crude product as a white solid. The crude product was triturated with ethyl acetate/petroleum ether (1/2) to yield the pure product as a white solid. Single crystals suitable for X-ray diffraction were obtained through slow evaporation of a solution of the pure title compound in ethyl acetate/petroleum ether (1/2 by volume).
N- and O-bound H atoms were located on a difference map and isotropically refined. C-bound H atoms were geometrically positioned (C–H = 0.95–0.99 Å), and included in the final cycles of
using a riding model, with Uiso(H) = 1.2–1.5Ueq(C).Data collection: CrystalClear (Rigaku/MSC, 2009); cell
CrystalClear (Rigaku/MSC, 2009); data reduction: CrystalClear (Rigaku/MSC, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).Fig. 1. View of the title compound showing the atomic numbering and 40% probability displacement ellipsoids. For the disordered atoms, only major parts are shown. |
C34H41N7O5·4H2O | Z = 2 |
Mr = 699.80 | F(000) = 748 |
Triclinic, P1 | Dx = 1.278 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.1140 (13) Å | Cell parameters from 6648 reflections |
b = 10.9700 (14) Å | θ = 1.9–27.9° |
c = 18.3830 (17) Å | µ = 0.09 mm−1 |
α = 88.51 (1)° | T = 113 K |
β = 85.455 (9)° | Prism, colourless |
γ = 83.034 (12)° | 0.22 × 0.20 × 0.18 mm |
V = 1818.4 (4) Å3 |
Rigaku Saturn 724 CCD area-detector diffractometer | 8627 independent reflections |
Radiation source: rotating anode | 5187 reflections with I > 2σ(I) |
Multilayer monochromator | Rint = 0.036 |
Detector resolution: 14.222 pixels mm-1 | θmax = 27.9°, θmin = 1.9° |
ω and ϕ scans | h = −11→11 |
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2009) | k = −14→14 |
Tmin = 0.980, Tmax = 0.983 | l = −24→24 |
23569 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.039 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.103 | w = 1/[σ2(Fo2) + (0.0522P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.96 | (Δ/σ)max = 0.003 |
8627 reflections | Δρmax = 0.42 e Å−3 |
513 parameters | Δρmin = −0.37 e Å−3 |
40 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0080 (11) |
C34H41N7O5·4H2O | γ = 83.034 (12)° |
Mr = 699.80 | V = 1818.4 (4) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.1140 (13) Å | Mo Kα radiation |
b = 10.9700 (14) Å | µ = 0.09 mm−1 |
c = 18.3830 (17) Å | T = 113 K |
α = 88.51 (1)° | 0.22 × 0.20 × 0.18 mm |
β = 85.455 (9)° |
Rigaku Saturn 724 CCD area-detector diffractometer | 8627 independent reflections |
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2009) | 5187 reflections with I > 2σ(I) |
Tmin = 0.980, Tmax = 0.983 | Rint = 0.036 |
23569 measured reflections |
R[F2 > 2σ(F2)] = 0.039 | 40 restraints |
wR(F2) = 0.103 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.96 | Δρmax = 0.42 e Å−3 |
8627 reflections | Δρmin = −0.37 e Å−3 |
513 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 | Occ. (<1) | |
O1 | −0.07658 (10) | 0.08373 (9) | 0.62025 (5) | 0.0267 (2) | |
O2 | 0.17115 (10) | 0.05322 (9) | 0.62048 (5) | 0.0270 (2) | |
O3 | 0.42751 (11) | 1.14550 (9) | 1.09974 (5) | 0.0287 (2) | |
O4 | 0.04154 (11) | 1.24401 (10) | 1.31026 (6) | 0.0381 (3) | |
O5 | 0.17441 (10) | 1.34627 (9) | 1.37972 (5) | 0.0279 (2) | |
O6 | 0.39167 (12) | 0.67342 (10) | 0.95328 (6) | 0.0275 (2) | |
O7 | 0.50826 (11) | 0.30578 (10) | 0.79165 (6) | 0.0295 (3) | |
O8 | 0.44104 (13) | 0.41395 (12) | 0.92879 (7) | 0.0384 (3) | |
O9 | 0.35290 (12) | 0.12591 (10) | 0.74559 (6) | 0.0312 (3) | |
N1 | −0.20452 (13) | 0.22911 (11) | 0.72416 (7) | 0.0235 (3) | |
N2 | 0.05361 (12) | 0.18903 (10) | 0.69881 (6) | 0.0203 (3) | |
N3 | 0.03535 (13) | 0.61137 (11) | 0.93156 (7) | 0.0240 (3) | |
N4 | −0.10668 (11) | 0.85922 (10) | 1.05945 (6) | 0.0183 (2) | |
N5 | 0.12518 (11) | 0.79155 (10) | 1.01673 (6) | 0.0192 (2) | |
N6 | 0.35894 (11) | 1.13593 (10) | 1.22064 (6) | 0.0189 (2) | |
N7 | 0.60387 (12) | 1.13966 (10) | 1.25116 (6) | 0.0224 (3) | |
C1 | −0.06690 (14) | 0.24665 (12) | 0.73487 (7) | 0.0181 (3) | |
C2 | −0.04330 (14) | 0.33887 (11) | 0.78872 (7) | 0.0176 (3) | |
C3 | 0.09907 (14) | 0.37209 (12) | 0.79453 (7) | 0.0203 (3) | |
H3 | 0.1804 | 0.3318 | 0.7653 | 0.024* | |
C4 | 0.12344 (14) | 0.46122 (12) | 0.84135 (7) | 0.0212 (3) | |
H4 | 0.2212 | 0.4814 | 0.8443 | 0.025* | |
C5 | 0.00592 (14) | 0.52322 (12) | 0.88503 (7) | 0.0187 (3) | |
C6 | −0.13680 (14) | 0.49039 (12) | 0.88028 (7) | 0.0215 (3) | |
H6 | −0.2180 | 0.5307 | 0.9095 | 0.026* | |
C7 | −0.15985 (14) | 0.39941 (12) | 0.83304 (7) | 0.0213 (3) | |
H7 | −0.2571 | 0.3777 | 0.8307 | 0.026* | |
C8 | 0.03660 (15) | 0.10830 (12) | 0.64545 (7) | 0.0206 (3) | |
C9 | 0.17173 (15) | −0.03820 (13) | 0.56542 (8) | 0.0270 (3) | |
H9A | 0.1270 | −0.0005 | 0.5216 | 0.032* | |
H9B | 0.1133 | −0.1043 | 0.5842 | 0.032* | |
C10 | 0.33034 (16) | −0.09023 (14) | 0.54624 (8) | 0.0337 (4) | |
H10A | 0.3766 | −0.1134 | 0.5905 | 0.040* | 0.756 (10) |
H10B | 0.3820 | −0.0275 | 0.5222 | 0.040* | 0.756 (10) |
H10C | 0.3709 | −0.1281 | 0.5891 | 0.040* | 0.244 (10) |
H10D | 0.3863 | −0.0240 | 0.5312 | 0.040* | 0.244 (10) |
C11 | 0.3481 (5) | −0.1909 (4) | 0.4920 (3) | 0.0363 (10) | 0.756 (10) |
H11A | 0.3006 | −0.1595 | 0.4475 | 0.044* | 0.756 (10) |
H11B | 0.2939 | −0.2585 | 0.5125 | 0.044* | 0.756 (10) |
C12 | 0.5069 (4) | −0.2433 (3) | 0.4700 (2) | 0.0317 (8) | 0.756 (10) |
H12A | 0.5580 | −0.2657 | 0.5148 | 0.038* | 0.756 (10) |
H12B | 0.5578 | −0.1782 | 0.4440 | 0.038* | 0.756 (10) |
C13 | 0.5237 (4) | −0.3553 (4) | 0.4216 (2) | 0.0413 (9) | 0.756 (10) |
H13A | 0.4765 | −0.4224 | 0.4476 | 0.050* | 0.756 (10) |
H13B | 0.4724 | −0.3345 | 0.3766 | 0.050* | 0.756 (10) |
C14 | 0.6862 (7) | −0.3987 (8) | 0.4014 (5) | 0.0448 (5) | 0.756 (10) |
H14A | 0.7345 | −0.3306 | 0.3788 | 0.067* | 0.756 (10) |
H14B | 0.6941 | −0.4663 | 0.3669 | 0.067* | 0.756 (10) |
H14C | 0.7347 | −0.4273 | 0.4454 | 0.067* | 0.756 (10) |
C11' | 0.3396 (14) | −0.2118 (12) | 0.5051 (9) | 0.0363 (10) | 0.244 (10) |
H11C | 0.2894 | −0.2720 | 0.5360 | 0.044* | 0.244 (10) |
H11D | 0.2871 | −0.1973 | 0.4600 | 0.044* | 0.244 (10) |
C12' | 0.4992 (14) | −0.2644 (12) | 0.4854 (7) | 0.0317 (8) | 0.244 (10) |
H12C | 0.5631 | −0.1990 | 0.4909 | 0.038* | 0.244 (10) |
H12D | 0.5270 | −0.3304 | 0.5213 | 0.038* | 0.244 (10) |
C13' | 0.5337 (14) | −0.3157 (13) | 0.4106 (6) | 0.0413 (9) | 0.244 (10) |
H13C | 0.5348 | −0.2470 | 0.3746 | 0.050* | 0.244 (10) |
H13D | 0.4542 | −0.3646 | 0.3993 | 0.050* | 0.244 (10) |
C14' | 0.683 (2) | −0.397 (2) | 0.4025 (14) | 0.0448 (5) | 0.244 (10) |
H14D | 0.7121 | −0.4104 | 0.3506 | 0.067* | 0.244 (10) |
H14E | 0.6737 | −0.4758 | 0.4274 | 0.067* | 0.244 (10) |
H14F | 0.7582 | −0.3559 | 0.4243 | 0.067* | 0.244 (10) |
C15 | −0.08019 (14) | 0.68470 (12) | 0.97473 (7) | 0.0200 (3) | |
H15A | −0.1329 | 0.6308 | 1.0090 | 0.024* | |
H15B | −0.1528 | 0.7268 | 0.9423 | 0.024* | |
C16 | −0.01657 (14) | 0.77783 (12) | 1.01663 (7) | 0.0183 (3) | |
C17 | −0.01616 (14) | 0.93177 (12) | 1.09055 (7) | 0.0179 (3) | |
C18 | 0.12911 (14) | 0.88895 (11) | 1.06367 (7) | 0.0174 (3) | |
C19 | 0.24838 (14) | 0.94473 (12) | 1.08399 (7) | 0.0194 (3) | |
H19 | 0.3469 | 0.9177 | 1.0655 | 0.023* | |
C20 | 0.21816 (14) | 1.04163 (12) | 1.13237 (7) | 0.0194 (3) | |
C21 | 0.07151 (15) | 1.08313 (12) | 1.15878 (7) | 0.0210 (3) | |
H21 | 0.0545 | 1.1496 | 1.1917 | 0.025* | |
C22 | −0.04793 (15) | 1.02964 (12) | 1.13805 (7) | 0.0209 (3) | |
H22 | −0.1468 | 1.0583 | 1.1554 | 0.025* | |
C23 | −0.26885 (14) | 0.86874 (13) | 1.07118 (8) | 0.0249 (3) | |
H23A | −0.3103 | 0.8480 | 1.0261 | 0.030* | |
H23B | −0.3081 | 0.9529 | 1.0848 | 0.030* | |
H23C | −0.2964 | 0.8117 | 1.1104 | 0.030* | |
C24 | 0.34361 (14) | 1.10995 (12) | 1.14951 (7) | 0.0201 (3) | |
C25 | 0.47803 (14) | 1.20529 (12) | 1.23399 (7) | 0.0189 (3) | |
C26 | 0.45451 (15) | 1.33195 (12) | 1.23265 (8) | 0.0236 (3) | |
H26 | 0.3627 | 1.3745 | 1.2200 | 0.028* | |
C27 | 0.56949 (15) | 1.39514 (13) | 1.25036 (8) | 0.0267 (3) | |
H27 | 0.5577 | 1.4824 | 1.2504 | 0.032* | |
C28 | 0.70211 (15) | 1.32896 (13) | 1.26806 (8) | 0.0259 (3) | |
H28 | 0.7828 | 1.3700 | 1.2800 | 0.031* | |
C29 | 0.71403 (15) | 1.20250 (13) | 1.26791 (7) | 0.0244 (3) | |
H29 | 0.8047 | 1.1575 | 1.2803 | 0.029* | |
C30 | 0.30221 (15) | 1.06478 (12) | 1.28412 (7) | 0.0219 (3) | |
H30A | 0.3766 | 0.9940 | 1.2941 | 0.026* | |
H30B | 0.2105 | 1.0322 | 1.2722 | 0.026* | |
C31 | 0.26932 (15) | 1.14206 (13) | 1.35196 (7) | 0.0244 (3) | |
H31A | 0.2390 | 1.0891 | 1.3935 | 0.029* | |
H31B | 0.3611 | 1.1749 | 1.3636 | 0.029* | |
C32 | 0.14955 (15) | 1.24727 (14) | 1.34383 (7) | 0.0250 (3) | |
C33 | 0.06161 (17) | 1.45193 (14) | 1.37596 (9) | 0.0335 (4) | |
H33A | −0.0344 | 1.4315 | 1.3990 | 0.040* | |
H33B | 0.0483 | 1.4764 | 1.3245 | 0.040* | |
C34 | 0.11330 (19) | 1.55442 (14) | 1.41568 (9) | 0.0388 (4) | |
H34A | 0.1276 | 1.5286 | 1.4663 | 0.047* | |
H34B | 0.0388 | 1.6267 | 1.4150 | 0.047* | |
H34C | 0.2073 | 1.5749 | 1.3917 | 0.047* | |
H1 | −0.2851 (19) | 0.2647 (16) | 0.7500 (10) | 0.050 (5)* | |
H2 | −0.2158 (17) | 0.1769 (14) | 0.6885 (9) | 0.033 (4)* | |
H5 | 0.1212 (17) | 0.6292 (14) | 0.9290 (8) | 0.034 (5)* | |
H8 | 0.307 (2) | 0.7148 (16) | 0.9744 (10) | 0.055 (6)* | |
H16 | 0.442 (2) | 0.7259 (17) | 0.9336 (10) | 0.057 (6)* | |
H17 | 0.482 (2) | 0.3315 (17) | 0.8352 (11) | 0.059 (6)* | |
H18 | 0.455 (2) | 0.2495 (17) | 0.7780 (10) | 0.053 (6)* | |
H20 | 0.263 (3) | 0.145 (2) | 0.7243 (12) | 0.085 (7)* | |
H24 | 0.367 (2) | 0.0486 (17) | 0.7441 (10) | 0.051 (6)* | |
H25 | 0.431 (2) | 0.4908 (19) | 0.9311 (11) | 0.068 (7)* | |
H32 | 0.502 (2) | 0.3853 (17) | 0.9665 (11) | 0.061 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0211 (5) | 0.0330 (6) | 0.0271 (5) | −0.0033 (4) | −0.0044 (4) | −0.0115 (4) |
O2 | 0.0199 (5) | 0.0321 (6) | 0.0289 (5) | −0.0010 (4) | −0.0004 (4) | −0.0144 (5) |
O3 | 0.0310 (6) | 0.0362 (6) | 0.0221 (5) | −0.0181 (5) | 0.0004 (4) | −0.0038 (4) |
O4 | 0.0240 (6) | 0.0475 (7) | 0.0435 (7) | 0.0025 (5) | −0.0132 (5) | −0.0163 (6) |
O5 | 0.0264 (5) | 0.0280 (6) | 0.0297 (6) | −0.0008 (4) | −0.0064 (4) | −0.0042 (5) |
O6 | 0.0232 (6) | 0.0238 (6) | 0.0345 (6) | −0.0029 (5) | 0.0040 (5) | −0.0018 (5) |
O7 | 0.0228 (5) | 0.0303 (6) | 0.0367 (7) | −0.0089 (5) | 0.0025 (5) | −0.0116 (5) |
O8 | 0.0460 (7) | 0.0293 (7) | 0.0413 (7) | 0.0022 (6) | −0.0193 (6) | −0.0113 (6) |
O9 | 0.0274 (6) | 0.0215 (6) | 0.0468 (7) | −0.0018 (5) | −0.0143 (5) | −0.0088 (5) |
N1 | 0.0188 (6) | 0.0264 (7) | 0.0262 (7) | −0.0043 (5) | −0.0017 (5) | −0.0116 (6) |
N2 | 0.0185 (6) | 0.0215 (6) | 0.0212 (6) | −0.0016 (5) | −0.0024 (5) | −0.0059 (5) |
N3 | 0.0166 (6) | 0.0257 (7) | 0.0309 (7) | −0.0055 (5) | −0.0013 (5) | −0.0107 (5) |
N4 | 0.0158 (5) | 0.0206 (6) | 0.0196 (6) | −0.0059 (5) | −0.0013 (4) | −0.0028 (5) |
N5 | 0.0189 (6) | 0.0190 (6) | 0.0205 (6) | −0.0036 (5) | −0.0030 (5) | −0.0022 (5) |
N6 | 0.0169 (6) | 0.0213 (6) | 0.0200 (6) | −0.0065 (5) | −0.0029 (4) | −0.0028 (5) |
N7 | 0.0189 (6) | 0.0220 (6) | 0.0268 (6) | −0.0024 (5) | −0.0039 (5) | −0.0039 (5) |
C1 | 0.0186 (7) | 0.0169 (7) | 0.0190 (7) | −0.0029 (5) | −0.0023 (5) | 0.0010 (5) |
C2 | 0.0191 (7) | 0.0160 (6) | 0.0180 (6) | −0.0027 (5) | −0.0033 (5) | 0.0003 (5) |
C3 | 0.0168 (6) | 0.0220 (7) | 0.0213 (7) | 0.0005 (6) | −0.0012 (5) | −0.0027 (6) |
C4 | 0.0151 (6) | 0.0236 (7) | 0.0258 (7) | −0.0052 (6) | −0.0032 (5) | −0.0016 (6) |
C5 | 0.0206 (7) | 0.0167 (7) | 0.0195 (7) | −0.0034 (5) | −0.0042 (5) | −0.0020 (5) |
C6 | 0.0179 (7) | 0.0214 (7) | 0.0248 (7) | −0.0014 (6) | 0.0004 (6) | −0.0069 (6) |
C7 | 0.0170 (7) | 0.0218 (7) | 0.0261 (7) | −0.0054 (6) | −0.0026 (6) | −0.0028 (6) |
C8 | 0.0204 (7) | 0.0207 (7) | 0.0207 (7) | −0.0032 (6) | 0.0005 (6) | −0.0012 (6) |
C9 | 0.0268 (8) | 0.0300 (8) | 0.0240 (7) | 0.0000 (6) | −0.0027 (6) | −0.0123 (6) |
C10 | 0.0250 (8) | 0.0403 (9) | 0.0347 (9) | 0.0004 (7) | 0.0018 (7) | −0.0148 (7) |
C11 | 0.0340 (10) | 0.0424 (17) | 0.031 (2) | 0.0088 (11) | −0.0096 (11) | −0.0134 (16) |
C12 | 0.0310 (10) | 0.0351 (15) | 0.0277 (18) | 0.0004 (11) | −0.0002 (11) | −0.0059 (12) |
C13 | 0.0365 (11) | 0.039 (2) | 0.0472 (16) | 0.0086 (16) | −0.0096 (10) | −0.0161 (16) |
C14 | 0.0372 (10) | 0.0537 (13) | 0.0410 (11) | 0.0068 (8) | −0.0023 (8) | −0.0127 (9) |
C11' | 0.0340 (10) | 0.0424 (17) | 0.031 (2) | 0.0088 (11) | −0.0096 (11) | −0.0134 (16) |
C12' | 0.0310 (10) | 0.0351 (15) | 0.0277 (18) | 0.0004 (11) | −0.0002 (11) | −0.0059 (12) |
C13' | 0.0365 (11) | 0.039 (2) | 0.0472 (16) | 0.0086 (16) | −0.0096 (10) | −0.0161 (16) |
C14' | 0.0372 (10) | 0.0537 (13) | 0.0410 (11) | 0.0068 (8) | −0.0023 (8) | −0.0127 (9) |
C15 | 0.0202 (7) | 0.0187 (7) | 0.0221 (7) | −0.0051 (6) | −0.0025 (5) | −0.0027 (6) |
C16 | 0.0203 (7) | 0.0172 (7) | 0.0179 (6) | −0.0036 (6) | −0.0024 (5) | 0.0007 (5) |
C17 | 0.0186 (7) | 0.0179 (7) | 0.0182 (6) | −0.0059 (5) | −0.0031 (5) | 0.0006 (5) |
C18 | 0.0186 (6) | 0.0159 (6) | 0.0179 (6) | −0.0024 (5) | −0.0020 (5) | −0.0006 (5) |
C19 | 0.0165 (6) | 0.0208 (7) | 0.0213 (7) | −0.0031 (5) | −0.0029 (5) | 0.0002 (6) |
C20 | 0.0215 (7) | 0.0190 (7) | 0.0189 (7) | −0.0063 (6) | −0.0043 (5) | 0.0012 (5) |
C21 | 0.0240 (7) | 0.0194 (7) | 0.0204 (7) | −0.0041 (6) | −0.0022 (6) | −0.0044 (6) |
C22 | 0.0174 (7) | 0.0237 (7) | 0.0218 (7) | −0.0030 (6) | −0.0010 (5) | −0.0042 (6) |
C23 | 0.0173 (7) | 0.0318 (8) | 0.0269 (8) | −0.0078 (6) | 0.0000 (6) | −0.0059 (6) |
C24 | 0.0184 (7) | 0.0197 (7) | 0.0225 (7) | −0.0027 (6) | −0.0020 (5) | −0.0031 (6) |
C25 | 0.0163 (6) | 0.0223 (7) | 0.0187 (7) | −0.0040 (6) | −0.0019 (5) | −0.0041 (6) |
C26 | 0.0209 (7) | 0.0221 (7) | 0.0277 (8) | −0.0009 (6) | −0.0041 (6) | −0.0007 (6) |
C27 | 0.0283 (8) | 0.0196 (7) | 0.0332 (8) | −0.0063 (6) | −0.0031 (6) | −0.0028 (6) |
C28 | 0.0221 (7) | 0.0271 (8) | 0.0303 (8) | −0.0080 (6) | −0.0044 (6) | −0.0057 (6) |
C29 | 0.0176 (7) | 0.0284 (8) | 0.0281 (8) | −0.0037 (6) | −0.0051 (6) | −0.0040 (6) |
C30 | 0.0203 (7) | 0.0235 (7) | 0.0229 (7) | −0.0060 (6) | −0.0028 (6) | −0.0001 (6) |
C31 | 0.0211 (7) | 0.0318 (8) | 0.0213 (7) | −0.0061 (6) | −0.0042 (6) | −0.0006 (6) |
C32 | 0.0203 (7) | 0.0345 (8) | 0.0209 (7) | −0.0067 (6) | −0.0001 (6) | −0.0049 (6) |
C33 | 0.0331 (9) | 0.0330 (9) | 0.0335 (9) | 0.0036 (7) | −0.0078 (7) | −0.0015 (7) |
C34 | 0.0444 (10) | 0.0295 (9) | 0.0431 (10) | −0.0031 (8) | −0.0084 (8) | −0.0015 (8) |
O1—C8 | 1.2251 (15) | C12—H12A | 0.9900 |
O2—C8 | 1.3510 (15) | C12—H12B | 0.9900 |
O2—C9 | 1.4425 (15) | C13—C14 | 1.520 (5) |
O3—C24 | 1.2316 (16) | C13—H13A | 0.9900 |
O4—C32 | 1.2071 (16) | C13—H13B | 0.9900 |
O5—C32 | 1.3367 (16) | C14—H14A | 0.9800 |
O5—C33 | 1.4571 (17) | C14—H14B | 0.9800 |
O6—H8 | 0.912 (19) | C14—H14C | 0.9800 |
O6—H16 | 0.84 (2) | C11'—C12' | 1.519 (9) |
O7—H17 | 0.861 (19) | C11'—H11C | 0.9900 |
O7—H18 | 0.881 (18) | C11'—H11D | 0.9900 |
O8—H25 | 0.84 (2) | C12'—C13' | 1.495 (9) |
O8—H32 | 0.94 (2) | C12'—H12C | 0.9900 |
O9—H20 | 0.93 (2) | C12'—H12D | 0.9900 |
O9—H24 | 0.844 (19) | C13'—C14' | 1.530 (9) |
N1—C1 | 1.3223 (16) | C13'—H13C | 0.9900 |
N1—H1 | 0.896 (17) | C13'—H13D | 0.9900 |
N1—H2 | 0.902 (15) | C14'—H14D | 0.9800 |
N2—C1 | 1.3354 (16) | C14'—H14E | 0.9800 |
N2—C8 | 1.3688 (16) | C14'—H14F | 0.9800 |
N3—C5 | 1.3713 (16) | C15—C16 | 1.4928 (17) |
N3—C15 | 1.4426 (17) | C15—H15A | 0.9900 |
N3—H5 | 0.826 (15) | C15—H15B | 0.9900 |
N4—C16 | 1.3593 (16) | C17—C22 | 1.3901 (17) |
N4—C17 | 1.3780 (15) | C17—C18 | 1.4054 (17) |
N4—C23 | 1.4680 (16) | C18—C19 | 1.3904 (17) |
N5—C16 | 1.3188 (16) | C19—C20 | 1.3914 (18) |
N5—C18 | 1.3963 (15) | C19—H19 | 0.9500 |
N6—C24 | 1.3669 (16) | C20—C21 | 1.4109 (18) |
N6—C25 | 1.4386 (16) | C20—C24 | 1.4985 (17) |
N6—C30 | 1.4810 (17) | C21—C22 | 1.3809 (17) |
N7—C25 | 1.3337 (17) | C21—H21 | 0.9500 |
N7—C29 | 1.3438 (16) | C22—H22 | 0.9500 |
C1—C2 | 1.4794 (17) | C23—H23A | 0.9800 |
C2—C7 | 1.3975 (18) | C23—H23B | 0.9800 |
C2—C3 | 1.4023 (17) | C23—H23C | 0.9800 |
C3—C4 | 1.3685 (17) | C25—C26 | 1.3798 (18) |
C3—H3 | 0.9500 | C26—C27 | 1.3881 (18) |
C4—C5 | 1.4036 (18) | C26—H26 | 0.9500 |
C4—H4 | 0.9500 | C27—C28 | 1.390 (2) |
C5—C6 | 1.4010 (18) | C27—H27 | 0.9500 |
C6—C7 | 1.3854 (17) | C28—C29 | 1.3784 (19) |
C6—H6 | 0.9500 | C28—H28 | 0.9500 |
C7—H7 | 0.9500 | C29—H29 | 0.9500 |
C9—C10 | 1.5064 (19) | C30—C31 | 1.5159 (18) |
C9—H9A | 0.9900 | C30—H30A | 0.9900 |
C9—H9B | 0.9900 | C30—H30B | 0.9900 |
C10—C11 | 1.494 (3) | C31—C32 | 1.502 (2) |
C10—C11' | 1.540 (9) | C31—H31A | 0.9900 |
C10—H10A | 0.9601 | C31—H31B | 0.9900 |
C10—H10B | 0.9600 | C33—C34 | 1.498 (2) |
C10—H10C | 0.9601 | C33—H33A | 0.9900 |
C10—H10D | 0.9601 | C33—H33B | 0.9900 |
C11—C12 | 1.519 (3) | C34—H34A | 0.9800 |
C11—H11A | 0.9900 | C34—H34B | 0.9800 |
C11—H11B | 0.9900 | C34—H34C | 0.9800 |
C12—C13 | 1.522 (4) | ||
C8—O2—C9 | 116.08 (10) | C13'—C12'—C11' | 116.6 (9) |
C32—O5—C33 | 115.53 (11) | C13'—C12'—H12C | 108.1 |
H8—O6—H16 | 107.3 (16) | C11'—C12'—H12C | 108.1 |
H17—O7—H18 | 113.2 (17) | C13'—C12'—H12D | 108.1 |
H25—O8—H32 | 105.7 (17) | C11'—C12'—H12D | 108.1 |
H20—O9—H24 | 103.2 (16) | H12C—C12'—H12D | 107.3 |
C1—N1—H1 | 124.5 (10) | C12'—C13'—C14' | 112.8 (9) |
C1—N1—H2 | 116.5 (10) | C12'—C13'—H13C | 109.0 |
H1—N1—H2 | 119.1 (14) | C14'—C13'—H13C | 109.0 |
C1—N2—C8 | 119.06 (11) | C12'—C13'—H13D | 109.0 |
C5—N3—C15 | 122.41 (11) | C14'—C13'—H13D | 109.0 |
C5—N3—H5 | 116.9 (10) | H13C—C13'—H13D | 107.8 |
C15—N3—H5 | 120.0 (10) | C13'—C14'—H14D | 109.5 |
C16—N4—C17 | 106.66 (10) | C13'—C14'—H14E | 109.5 |
C16—N4—C23 | 127.23 (11) | H14D—C14'—H14E | 109.5 |
C17—N4—C23 | 126.11 (11) | C13'—C14'—H14F | 109.5 |
C16—N5—C18 | 104.75 (10) | H14D—C14'—H14F | 109.5 |
C24—N6—C25 | 116.67 (10) | H14E—C14'—H14F | 109.5 |
C24—N6—C30 | 124.33 (10) | N3—C15—C16 | 110.61 (11) |
C25—N6—C30 | 115.31 (10) | N3—C15—H15A | 109.5 |
C25—N7—C29 | 117.00 (12) | C16—C15—H15A | 109.5 |
N1—C1—N2 | 124.48 (12) | N3—C15—H15B | 109.5 |
N1—C1—C2 | 118.39 (12) | C16—C15—H15B | 109.5 |
N2—C1—C2 | 117.10 (11) | H15A—C15—H15B | 108.1 |
C7—C2—C3 | 117.59 (11) | N5—C16—N4 | 113.56 (11) |
C7—C2—C1 | 122.34 (11) | N5—C16—C15 | 125.99 (12) |
C3—C2—C1 | 120.02 (11) | N4—C16—C15 | 120.45 (11) |
C4—C3—C2 | 121.45 (12) | N4—C17—C22 | 131.62 (12) |
C4—C3—H3 | 119.3 | N4—C17—C18 | 105.80 (10) |
C2—C3—H3 | 119.3 | C22—C17—C18 | 122.57 (11) |
C3—C4—C5 | 120.90 (12) | C19—C18—N5 | 130.40 (12) |
C3—C4—H4 | 119.6 | C19—C18—C17 | 120.36 (11) |
C5—C4—H4 | 119.6 | N5—C18—C17 | 109.23 (10) |
N3—C5—C6 | 122.64 (12) | C18—C19—C20 | 117.59 (12) |
N3—C5—C4 | 119.02 (12) | C18—C19—H19 | 121.2 |
C6—C5—C4 | 118.33 (11) | C20—C19—H19 | 121.2 |
C7—C6—C5 | 120.21 (12) | C19—C20—C21 | 121.15 (11) |
C7—C6—H6 | 119.9 | C19—C20—C24 | 118.17 (12) |
C5—C6—H6 | 119.9 | C21—C20—C24 | 120.35 (11) |
C6—C7—C2 | 121.51 (12) | C22—C21—C20 | 121.72 (12) |
C6—C7—H7 | 119.2 | C22—C21—H21 | 119.1 |
C2—C7—H7 | 119.2 | C20—C21—H21 | 119.1 |
O1—C8—O2 | 120.94 (11) | C21—C22—C17 | 116.59 (12) |
O1—C8—N2 | 129.76 (12) | C21—C22—H22 | 121.7 |
O2—C8—N2 | 109.30 (11) | C17—C22—H22 | 121.7 |
O2—C9—C10 | 107.93 (11) | N4—C23—H23A | 109.5 |
O2—C9—H9A | 110.1 | N4—C23—H23B | 109.5 |
C10—C9—H9A | 110.1 | H23A—C23—H23B | 109.5 |
O2—C9—H9B | 110.1 | N4—C23—H23C | 109.5 |
C10—C9—H9B | 110.1 | H23A—C23—H23C | 109.5 |
H9A—C9—H9B | 108.4 | H23B—C23—H23C | 109.5 |
C11—C10—C9 | 114.1 (2) | O3—C24—N6 | 121.11 (11) |
C11—C10—C11' | 12.7 (8) | O3—C24—C20 | 120.02 (12) |
C9—C10—C11' | 111.3 (5) | N6—C24—C20 | 118.82 (11) |
C11—C10—H10A | 113.1 | N7—C25—C26 | 124.33 (12) |
C9—C10—H10A | 108.8 | N7—C25—N6 | 115.85 (11) |
C11'—C10—H10A | 103.9 | C26—C25—N6 | 119.71 (12) |
C11—C10—H10B | 103.7 | C25—C26—C27 | 117.78 (13) |
C9—C10—H10B | 108.9 | C25—C26—H26 | 121.1 |
C11'—C10—H10B | 115.7 | C27—C26—H26 | 121.1 |
H10A—C10—H10B | 107.9 | C26—C27—C28 | 119.05 (13) |
C11—C10—H10C | 104.4 | C26—C27—H27 | 120.5 |
C9—C10—H10C | 108.9 | C28—C27—H27 | 120.5 |
C11'—C10—H10C | 94.3 | C29—C28—C27 | 118.55 (13) |
H10A—C10—H10C | 10.7 | C29—C28—H28 | 120.7 |
H10B—C10—H10C | 117.0 | C27—C28—H28 | 120.7 |
C11—C10—H10D | 112.7 | N7—C29—C28 | 123.29 (13) |
C9—C10—H10D | 108.7 | N7—C29—H29 | 118.4 |
C11'—C10—H10D | 124.1 | C28—C29—H29 | 118.4 |
H10A—C10—H10D | 98.3 | N6—C30—C31 | 112.12 (11) |
H10B—C10—H10D | 10.7 | N6—C30—H30A | 109.2 |
H10C—C10—H10D | 107.9 | C31—C30—H30A | 109.2 |
C10—C11—C12 | 115.4 (3) | N6—C30—H30B | 109.2 |
C10—C11—H11A | 108.4 | C31—C30—H30B | 109.2 |
C12—C11—H11A | 108.4 | H30A—C30—H30B | 107.9 |
C10—C11—H11B | 108.4 | C32—C31—C30 | 113.14 (11) |
C12—C11—H11B | 108.4 | C32—C31—H31A | 109.0 |
H11A—C11—H11B | 107.5 | C30—C31—H31A | 109.0 |
C11—C12—C13 | 115.1 (3) | C32—C31—H31B | 109.0 |
C11—C12—H12A | 108.5 | C30—C31—H31B | 109.0 |
C13—C12—H12A | 108.5 | H31A—C31—H31B | 107.8 |
C11—C12—H12B | 108.5 | O4—C32—O5 | 123.06 (14) |
C13—C12—H12B | 108.5 | O4—C32—C31 | 124.96 (13) |
H12A—C12—H12B | 107.5 | O5—C32—C31 | 111.97 (11) |
C14—C13—C12 | 110.9 (4) | O5—C33—C34 | 107.38 (12) |
C14—C13—H13A | 109.5 | O5—C33—H33A | 110.2 |
C12—C13—H13A | 109.5 | C34—C33—H33A | 110.2 |
C14—C13—H13B | 109.5 | O5—C33—H33B | 110.2 |
C12—C13—H13B | 109.5 | C34—C33—H33B | 110.2 |
H13A—C13—H13B | 108.0 | H33A—C33—H33B | 108.5 |
C12'—C11'—C10 | 111.6 (9) | C33—C34—H34A | 109.5 |
C12'—C11'—H11C | 109.3 | C33—C34—H34B | 109.5 |
C10—C11'—H11C | 109.3 | H34A—C34—H34B | 109.5 |
C12'—C11'—H11D | 109.3 | C33—C34—H34C | 109.5 |
C10—C11'—H11D | 109.3 | H34A—C34—H34C | 109.5 |
H11C—C11'—H11D | 108.0 | H34B—C34—H34C | 109.5 |
C8—N2—C1—N1 | 1.9 (2) | C23—N4—C17—C18 | 179.88 (12) |
C8—N2—C1—C2 | −176.19 (12) | C16—N5—C18—C19 | −179.11 (14) |
N1—C1—C2—C7 | 6.0 (2) | C16—N5—C18—C17 | −0.32 (14) |
N2—C1—C2—C7 | −175.86 (12) | N4—C17—C18—C19 | 179.02 (12) |
N1—C1—C2—C3 | −171.36 (12) | C22—C17—C18—C19 | −0.2 (2) |
N2—C1—C2—C3 | 6.82 (19) | N4—C17—C18—N5 | 0.08 (14) |
C7—C2—C3—C4 | −0.6 (2) | C22—C17—C18—N5 | −179.18 (12) |
C1—C2—C3—C4 | 176.89 (13) | N5—C18—C19—C20 | 179.84 (13) |
C2—C3—C4—C5 | −0.4 (2) | C17—C18—C19—C20 | 1.16 (19) |
C15—N3—C5—C6 | −5.5 (2) | C18—C19—C20—C21 | −1.1 (2) |
C15—N3—C5—C4 | 175.89 (12) | C18—C19—C20—C24 | −174.58 (12) |
C3—C4—C5—N3 | 179.58 (13) | C19—C20—C21—C22 | 0.1 (2) |
C3—C4—C5—C6 | 0.9 (2) | C24—C20—C21—C22 | 173.45 (13) |
N3—C5—C6—C7 | −179.07 (13) | C20—C21—C22—C17 | 0.8 (2) |
C4—C5—C6—C7 | −0.4 (2) | N4—C17—C22—C21 | −179.80 (13) |
C5—C6—C7—C2 | −0.5 (2) | C18—C17—C22—C21 | −0.7 (2) |
C3—C2—C7—C6 | 1.0 (2) | C25—N6—C24—O3 | −0.57 (19) |
C1—C2—C7—C6 | −176.37 (13) | C30—N6—C24—O3 | −157.83 (13) |
C9—O2—C8—O1 | −2.42 (19) | C25—N6—C24—C20 | −177.95 (11) |
C9—O2—C8—N2 | 177.92 (11) | C30—N6—C24—C20 | 24.79 (19) |
C1—N2—C8—O1 | 5.4 (2) | C19—C20—C24—O3 | 48.24 (19) |
C1—N2—C8—O2 | −174.95 (11) | C21—C20—C24—O3 | −125.29 (15) |
C8—O2—C9—C10 | −178.74 (12) | C19—C20—C24—N6 | −134.35 (13) |
O2—C9—C10—C11 | 177.3 (3) | C21—C20—C24—N6 | 52.12 (18) |
O2—C9—C10—C11' | 163.8 (8) | C29—N7—C25—C26 | −0.2 (2) |
C9—C10—C11—C12 | 178.5 (2) | C29—N7—C25—N6 | −176.35 (11) |
C11'—C10—C11—C12 | −101 (3) | C24—N6—C25—N7 | −95.43 (15) |
C10—C11—C12—C13 | 173.3 (5) | C30—N6—C25—N7 | 63.90 (15) |
C11—C12—C13—C14 | 178.7 (5) | C24—N6—C25—C26 | 88.23 (15) |
C11—C10—C11'—C12' | 75 (3) | C30—N6—C25—C26 | −112.44 (14) |
C9—C10—C11'—C12' | 179.8 (9) | N7—C25—C26—C27 | 0.0 (2) |
C10—C11'—C12'—C13' | −137.5 (15) | N6—C25—C26—C27 | 176.00 (12) |
C11'—C12'—C13'—C14' | −164.4 (16) | C25—C26—C27—C28 | 0.4 (2) |
C5—N3—C15—C16 | −176.57 (12) | C26—C27—C28—C29 | −0.5 (2) |
C18—N5—C16—N4 | 0.46 (15) | C25—N7—C29—C28 | 0.0 (2) |
C18—N5—C16—C15 | −179.85 (13) | C27—C28—C29—N7 | 0.3 (2) |
C17—N4—C16—N5 | −0.41 (15) | C24—N6—C30—C31 | −153.22 (12) |
C23—N4—C16—N5 | 179.89 (12) | C25—N6—C30—C31 | 49.24 (15) |
C17—N4—C16—C15 | 179.87 (12) | N6—C30—C31—C32 | 62.82 (15) |
C23—N4—C16—C15 | 0.2 (2) | C33—O5—C32—O4 | 0.0 (2) |
N3—C15—C16—N5 | −1.54 (19) | C33—O5—C32—C31 | −178.75 (12) |
N3—C15—C16—N4 | 178.13 (12) | C30—C31—C32—O4 | 36.1 (2) |
C16—N4—C17—C22 | 179.36 (14) | C30—C31—C32—O5 | −145.15 (12) |
C23—N4—C17—C22 | −0.9 (2) | C32—O5—C33—C34 | −176.98 (12) |
C16—N4—C17—C18 | 0.18 (14) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O7i | 0.896 (17) | 1.980 (18) | 2.8468 (16) | 162.5 (15) |
N1—H2···O1 | 0.902 (15) | 1.931 (16) | 2.6281 (16) | 132.7 (13) |
O6—H8···N5 | 0.912 (19) | 1.88 (2) | 2.7938 (16) | 176.3 (16) |
O6—H16···O3ii | 0.84 (2) | 2.00 (2) | 2.8373 (15) | 172.1 (18) |
O7—H17···O8 | 0.861 (19) | 1.954 (19) | 2.8061 (16) | 170.2 (18) |
O7—H18···O9 | 0.881 (18) | 1.871 (19) | 2.7513 (15) | 176.5 (17) |
O9—H20···N2 | 0.93 (2) | 2.00 (2) | 2.9226 (16) | 168.8 (19) |
O9—H20···O2 | 0.93 (2) | 2.43 (2) | 3.1126 (14) | 129.6 (16) |
O9—H24···N7iii | 0.844 (19) | 2.050 (19) | 2.8918 (16) | 175.5 (18) |
O8—H25···O6 | 0.84 (2) | 2.04 (2) | 2.8689 (17) | 171 (2) |
O8—H32···O6iii | 0.94 (2) | 1.89 (2) | 2.8291 (17) | 175.3 (17) |
Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y+2, −z+2; (iii) −x+1, −y+1, −z+2. |
Experimental details
Crystal data | |
Chemical formula | C34H41N7O5·4H2O |
Mr | 699.80 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 113 |
a, b, c (Å) | 9.1140 (13), 10.9700 (14), 18.3830 (17) |
α, β, γ (°) | 88.51 (1), 85.455 (9), 83.034 (12) |
V (Å3) | 1818.4 (4) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.22 × 0.20 × 0.18 |
Data collection | |
Diffractometer | Rigaku Saturn 724 CCD area-detector diffractometer |
Absorption correction | Multi-scan (CrystalClear; Rigaku/MSC, 2009) |
Tmin, Tmax | 0.980, 0.983 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 23569, 8627, 5187 |
Rint | 0.036 |
(sin θ/λ)max (Å−1) | 0.658 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.039, 0.103, 0.96 |
No. of reflections | 8627 |
No. of parameters | 513 |
No. of restraints | 40 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.42, −0.37 |
Computer programs: CrystalClear (Rigaku/MSC, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O7i | 0.896 (17) | 1.980 (18) | 2.8468 (16) | 162.5 (15) |
N1—H2···O1 | 0.902 (15) | 1.931 (16) | 2.6281 (16) | 132.7 (13) |
O6—H8···N5 | 0.912 (19) | 1.88 (2) | 2.7938 (16) | 176.3 (16) |
O6—H16···O3ii | 0.84 (2) | 2.00 (2) | 2.8373 (15) | 172.1 (18) |
O7—H17···O8 | 0.861 (19) | 1.954 (19) | 2.8061 (16) | 170.2 (18) |
O7—H18···O9 | 0.881 (18) | 1.871 (19) | 2.7513 (15) | 176.5 (17) |
O9—H20···N2 | 0.93 (2) | 2.00 (2) | 2.9226 (16) | 168.8 (19) |
O9—H20···O2 | 0.93 (2) | 2.43 (2) | 3.1126 (14) | 129.6 (16) |
O9—H24···N7iii | 0.844 (19) | 2.050 (19) | 2.8918 (16) | 175.5 (18) |
O8—H25···O6 | 0.84 (2) | 2.04 (2) | 2.8689 (17) | 171 (2) |
O8—H32···O6iii | 0.94 (2) | 1.89 (2) | 2.8291 (17) | 175.3 (17) |
Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y+2, −z+2; (iii) −x+1, −y+1, −z+2. |
References
Nagarakanti, R. & Ellis, C. R. (2012). Clin. Ther. 34, 2051–2060. Web of Science CrossRef CAS PubMed Google Scholar
Rigaku/MSC (2009). CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Van Ryn, J., Stangier, J., Haertter, S., Liesenfeld, K. H., Wienen, W., Feuring, M. & Clemens, A. (2010). Thromb. Haemost. 103, 1116–1127. Web of Science CrossRef CAS PubMed Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Dabigatran etexilate is an oral anticoagulant drug (Nagarakanti & Ellis 2012; Van Ryn et al., 2010). During our study on this drug, we obtained the single crystals of its tetrahydrate, which provides a valuable insight into the crystal structure of this drug.
In the title compound (Fig. 1), the benzene and pyridine rings form dihedral angles of 5.4 (1) and 43.8 (1)°, respectively, with the benzimidazole mean plane. The terminal butyl group is disordered over two conformations in a ratio 0.756 (1):0.244 (1). The crystalline water molecules are involved in formation of O—H···O, O—H···N and N—H···O hydrogen bonds (Table 1), which link all moieties into layers parallel to the ab plane.