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The crystal structure of the title compound, C8H16N2O3S·2C3H8O, is divided into hydro­phobic and hydro­philic layers. Two peptide mol­ecules in the asymmetric unit are related by pseudo-translational symmetry along the a axis, as are two of the four 2-propanol mol­ecules. The last two 2-propanol mol­ecules in the asymmetric unit have different relative orientations and hydrogen-bond interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100000548/qa0200sup1.cif
Contains datablocks I, default

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100000548/qa0200Isup2.hkl
Contains datablock I

CCDC reference: 142943

Comment top

Like several other dipeptides with two hydrophobic residues (Görbitz, 1999a,b, and references therein), the crystal structure of the title compound, (I), is divided into hydrophobic and hydrophilic layers, but the specific molecular arrangement is different from those observed previously. The two dipeptide molecules A and B in the asymmetric unit are stacked in an alternating sequence along the a axis with pseudo-translational symmetry. The geometries of the L-Met residues of A an B are almost identical, and both side chains are in the trans,trans,gauche- conformation for χ1, χ2 and χ3. The general pseudo-translational symmetry along the a axis includes the two 2-propanol solvent molecules C and F, but not D and E which have different orientations.

As expected, two of the three amino H atoms of each peptide molecule are engaged in hydrogen bonding in the hydrophilic layers, while 2-propanol molecules C and F, which are very similarly embedded in the hydrophobic layers, serve the important roles as acceptors for the remaining amino H atoms. The 2-propanol molecules C, D and F are donors in O—H···O—H interactions, but molecule E is unique in donating its hydroxylic H atom to a carboxylate group. The acceptor atom, O2B, is made available through a rotation of the carboxylate group compared with peptide molecule A, with N2—C6—C8—O2 = 11.5 (6)° compared to −13.2 (7)° for A. Unlike O2A, O2B can then no longer accept an amino H atom, which is instead accepted by O3B.

The unit cell for the thin needle-shaped crystals also obtained in the crystallization experiments has a = b = 14.2459 (12) Å, c = 9.7152 (11) Å, α = β = 90° and γ = 120°. An unambiguous determination of the space group was not possible, but we suspect that the structure is closely related to the hexagonal P61 structures of L-Val-L-Ala (Görbitz & Gundersen, 1996), L-Val-L-Val and L-Ala-L-Ile (Görbitz, 2000).

Experimental top

Crystals of the title compound were prepared by vapour diffusion of 2-propanol into 30 µl of an aqueous solution of the dipeptide. At low initial solute concentration (0.16–0.32 mg in 30 µl of water), bundles of exceedingly thin needles were formed which were too small for collection of X-ray data (<0.01 mm), but permitted determination of the unit cell. A second polymorph in the shape of ultrathin plates appeared (together with the needles) when higher concentrations were used. The plates are soft and easily bent, and can not be cut without inflicting substantial damage. They furthermore decay within a few s when exposed to air. The specimen used for data collection was obtained from a test tube containing 0.64 mg of the peptide, and was transferred to a drop of oil before being attached to the glass rod.

Thin plates were also obtained with 1-propanol as precipitating agent, but no unit cell was found for any of the crystals tested. 2-Butanol, on the other hand, gave very thin needles, while methanol and ethanol failed to give precipitates in the diffusion experiments.

Refinement top

The data collection nominally covered over a hemisphere of reciprocal space by a combination of three sets of exposures with the detector set at 2θ = 29° and a 4.95 cm crystal-to-detector distance.

Displacement ellipsoids for the solvent molecule are quite large, and for molecules C, E and F the disorder has been resolved into a major and a minor position, with occupancies 0.68 (2):0.32 (2), 0.896 (13):0.104 (13) and 0.806 (7):0.194 (7), respectively. For C and E, the disorder arises from a rotation around the O1—C2 bond, while for F, O1 and C2 are also shifted to alternative positions.

Heavy atoms were refined anisotropically, except for the O and C atoms of the least populated positions of the disordered 2-propanol molecules C, E and F, which were refined isotropically (C) or assigned Uiso values equivalent to Ueq for the corresponding atom in the most populated position. A mild SHELXTL (Sheldrick, 1997) SAME constraint (s1 = 0.006 and s2 = 0.009) was used for the geometry of the two peptide molecules, and similar commands (s1 = 0.008 and s2 = 0.012) for the geometry of all 2-propanol molecules. H atoms were placed geometrically and refined with a riding model which included free rotation for amino groups and methyl groups with occupancy greater than 0.5. Hydroxylic H atoms were constrained to have tetrahedral geometry and rotated so as to minimize the distance to the closest acceptor, but with deviations from perfect staggered positions not exceeding 30°. Uiso values were constrained to be 1.2Ueq of the carrier atom, or 1.5Ueq for methyl, hydroxyl and amino groups.

Computing details top

Data collection: SMART (Siemens, 1995); cell refinement: SAINT (Siemens, 1995); data reduction: SAINT (Siemens, 1995); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXTL (Sheldrick, 1997); software used to prepare material for publication: SHELXTL (Sheldrick, 1997).

L-Methionyl-L-alanine 2-propanol solvate top
Crystal data top
C8H16N2O3S·2C3H8OF(000) = 744
Mr = 340.48Dx = 1.118 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 9.9277 (2) ÅCell parameters from 4393 reflections
b = 16.4556 (3) Åθ = 2–25°
c = 12.4895 (2) ŵ = 0.18 mm1
β = 97.594 (1)°T = 150 K
V = 2022.47 (6) Å3Plate, colourless
Z = 40.80 × 0.48 × 0.01 mm
Data collection top
Siemens SMART CCD
diffractometer
6911 independent reflections
Radiation source: fine-focus sealed tube4437 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.093
Detector resolution: 8.3 pixels mm-1θmax = 25.0°, θmin = 2.1°
Sets of exposures each taken over 0.3° ω rotation scansh = 1111
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
k = 1919
Tmin = 0.865, Tmax = 0.998l = 1414
14839 measured reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.078 w = 1/[σ2(Fo2) + (0.040P)2 + 1.5P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.202(Δ/σ)max = 0.014
S = 1.01Δρmax = 0.53 e Å3
6911 reflectionsΔρmin = 0.30 e Å3
448 parametersExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
198 restraintsExtinction coefficient: 0.0070 (16)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), 3230 Friedel pairs
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.01 (16)
Crystal data top
C8H16N2O3S·2C3H8OV = 2022.47 (6) Å3
Mr = 340.48Z = 4
Monoclinic, P21Mo Kα radiation
a = 9.9277 (2) ŵ = 0.18 mm1
b = 16.4556 (3) ÅT = 150 K
c = 12.4895 (2) Å0.80 × 0.48 × 0.01 mm
β = 97.594 (1)°
Data collection top
Siemens SMART CCD
diffractometer
6911 independent reflections
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
4437 reflections with I > 2σ(I)
Tmin = 0.865, Tmax = 0.998Rint = 0.093
14839 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.078H-atom parameters constrained
wR(F2) = 0.202Δρmax = 0.53 e Å3
S = 1.01Δρmin = 0.30 e Å3
6911 reflectionsAbsolute structure: Flack (1983), 3230 Friedel pairs
448 parametersAbsolute structure parameter: 0.01 (16)
198 restraints
Special details top

Refinement. Flack parameter calculated from merging of 3230 Friedel pairs

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
S1A0.2282 (2)0.17232 (14)0.84163 (16)0.0915 (6)
O1A0.0601 (3)0.1049 (2)0.4775 (4)0.0619 (11)
O2A0.2888 (3)0.0977 (2)0.5129 (4)0.0611 (11)
O3A0.1201 (3)0.18671 (18)0.5102 (4)0.0618 (11)
N1A0.1041 (4)0.2411 (2)0.4313 (3)0.0439 (10)
H1A0.17040.27910.43010.066*
H2A0.02970.26450.45400.066*
H3A0.08130.22040.36380.066*
N2A0.1305 (3)0.02973 (19)0.4767 (3)0.0426 (10)
H4A0.21930.03130.47830.051*
C1A0.1548 (4)0.1741 (2)0.5073 (4)0.0432 (12)
H11A0.25000.16000.49650.052*
C2A0.1533 (5)0.2042 (3)0.6219 (4)0.0480 (12)
H21A0.05820.21050.63630.058*
H22A0.19800.25800.63050.058*
C3A0.2290 (7)0.1430 (3)0.7041 (5)0.0744 (18)
H31A0.32430.13790.68970.089*
H32A0.18570.08900.69270.089*
C4A0.3376 (8)0.2583 (5)0.8515 (6)0.097 (2)
H41A0.34730.27970.92530.145*
H42A0.29900.30030.80100.145*
H43A0.42700.24220.83350.145*
C5A0.0644 (4)0.0993 (2)0.4851 (4)0.0420 (12)
C6A0.0628 (4)0.0490 (2)0.4651 (4)0.0474 (13)
H61A0.00950.05040.51360.057*
C7A0.0025 (6)0.0630 (3)0.3503 (5)0.0719 (18)
H71A0.06110.01670.32640.108*
H72A0.05720.11270.34690.108*
H73A0.06830.06860.30300.108*
C8A0.1668 (4)0.1154 (2)0.5006 (4)0.0490 (13)
S1B0.2703 (2)0.66958 (15)0.16478 (17)0.0916 (6)
O1B0.5559 (3)0.6103 (2)0.5374 (3)0.0586 (11)
O2B0.2226 (3)0.4381 (2)0.4017 (3)0.0586 (10)
O3B0.3336 (3)0.33245 (18)0.4827 (3)0.0549 (10)
N1B0.4242 (4)0.7599 (2)0.5637 (3)0.0458 (11)
H1B0.37600.80660.54990.069*
H2B0.50950.76670.54590.069*
H3B0.42940.74760.63520.069*
N2B0.3525 (3)0.54732 (19)0.5299 (4)0.0470 (11)
H4B0.26410.55420.52600.056*
C1B0.3547 (4)0.6919 (2)0.4980 (4)0.0440 (13)
H11B0.25900.68670.51400.053*
C2B0.3545 (5)0.7129 (3)0.3797 (4)0.0520 (13)
H21B0.44870.71140.36190.062*
H22B0.31900.76870.36600.062*
C3B0.2648 (6)0.6517 (3)0.3058 (5)0.0714 (17)
H31B0.16960.65600.32070.086*
H32B0.29650.59570.32390.086*
C4B0.1806 (9)0.7636 (5)0.1482 (7)0.118 (3)
H41B0.17190.78030.07220.177*
H42B0.23060.80530.19320.177*
H43B0.08990.75690.16990.177*
C5B0.4308 (4)0.6124 (2)0.5257 (4)0.0437 (13)
C6B0.4068 (4)0.4650 (2)0.5406 (4)0.0481 (14)
H61B0.49650.46520.51240.058*
C7B0.4315 (6)0.4376 (3)0.6569 (5)0.0687 (17)
H71B0.50020.47250.69730.103*
H72B0.46360.38120.66010.103*
H73B0.34660.44110.68870.103*
C8B0.3124 (4)0.4089 (2)0.4687 (4)0.0448 (12)
O1C0.4489 (5)0.7337 (3)0.7847 (4)0.0997 (17)0.677 (18)
H1C0.48500.77030.82720.150*
C1C0.2379 (11)0.6617 (11)0.7601 (11)0.135 (6)0.677 (18)
H11C0.27540.61470.72590.203*0.677 (18)
H12C0.20700.70230.70480.203*0.677 (18)
H13C0.16100.64430.79620.203*0.677 (18)
C2C0.3459 (9)0.6983 (7)0.8417 (9)0.090 (7)0.677 (18)
H21C0.30560.74070.88530.108*0.677 (18)
C3C0.4142 (15)0.6342 (8)0.9137 (11)0.123 (6)0.677 (18)
H31C0.45800.59500.87040.185*0.677 (18)
H32C0.34670.60630.95100.185*0.677 (18)
H33C0.48300.65930.96710.185*0.677 (18)
O12C0.4489 (5)0.7337 (3)0.7847 (4)0.0997 (17)0.323 (18)
C12C0.2162 (14)0.7400 (19)0.807 (3)0.156 (16)*0.323 (18)
H14C0.21480.79910.81590.234*0.323 (18)
H15C0.14510.71530.84350.234*0.323 (18)
H16C0.19980.72680.72950.234*0.323 (18)
C22C0.3523 (15)0.7074 (12)0.8542 (14)0.108 (19)*0.323 (18)
H22C0.37800.72900.92890.130*0.323 (18)
C32C0.352 (3)0.6171 (12)0.855 (3)0.131 (13)*0.323 (18)
H34C0.44410.59710.87780.196*0.323 (18)
H35C0.31910.59680.78270.196*0.323 (18)
H36C0.29160.59780.90600.196*0.323 (18)
O1D0.5978 (4)0.1430 (2)0.8885 (3)0.0759 (12)
H1D0.66990.13420.86040.114*
C1D0.4878 (8)0.0328 (5)0.7862 (6)0.115 (3)
H11D0.56510.01760.74910.172*
H12D0.42970.01480.79150.172*
H13D0.43530.07570.74530.172*
C2D0.5387 (7)0.0632 (4)0.8970 (6)0.093 (2)
H21D0.61060.02530.93130.111*
C3D0.4306 (8)0.0697 (6)0.9676 (7)0.123 (3)
H31D0.47190.07841.04240.184*
H32D0.37120.11570.94410.184*
H33D0.37710.01950.96290.184*
O1E0.1652 (4)0.3782 (2)0.2026 (3)0.0696 (11)0.896 (13)
H1E0.18210.39870.26540.104*
C1E0.0471 (9)0.4478 (8)0.1984 (10)0.144 (5)0.896 (13)
H11E0.02600.48600.25840.216*0.896 (13)
H12E0.07500.39560.22630.216*0.896 (13)
H13E0.12120.46970.14680.216*0.896 (13)
C2E0.0755 (8)0.4357 (5)0.1434 (6)0.098 (3)0.896 (13)
H21E0.12390.48880.14090.117*0.896 (13)
C3E0.0437 (11)0.4037 (6)0.0316 (6)0.122 (4)0.896 (13)
H31E0.11340.42190.01180.182*0.896 (13)
H32E0.04530.42390.00060.182*0.896 (13)
H33E0.04220.34420.03360.182*0.896 (13)
O12E0.1652 (4)0.3782 (2)0.2026 (3)0.0696 (11)0.104 (13)
C12E0.003 (7)0.482 (4)0.209 (9)0.140*0.104 (13)
H14E0.06630.52280.23240.210*0.104 (13)
H15E0.03000.45430.27240.210*0.104 (13)
H16E0.08200.50770.16810.210*0.104 (13)
C22E0.055 (4)0.420 (3)0.139 (4)0.096*0.104 (13)
H22E0.09030.44880.07740.115*0.104 (13)
C32E0.048 (5)0.359 (5)0.096 (7)0.120*0.104 (13)
H34E0.00670.32040.05010.180*0.104 (13)
H35E0.12460.38630.05330.180*0.104 (13)
H36E0.07970.32990.15620.180*0.104 (13)
O1F0.1040 (7)0.2156 (3)0.2105 (5)0.090 (2)0.806 (7)
H1F0.09390.25930.17420.136*0.806 (7)
C1F0.0579 (10)0.1151 (7)0.0724 (9)0.119 (4)0.806 (7)
H11F0.00190.15370.02940.178*0.806 (7)
H12F0.00490.08330.11830.178*0.806 (7)
H13F0.09920.07850.02400.178*0.806 (7)
C2F0.1679 (7)0.1609 (5)0.1421 (6)0.077 (3)0.806 (7)
H21F0.22530.19190.09620.116*0.806 (7)
C3F0.2533 (13)0.1028 (7)0.2137 (10)0.146 (5)0.806 (7)
H31F0.33180.13170.25180.219*0.806 (7)
H32F0.28500.05920.16990.219*0.806 (7)
H33F0.19920.07960.26640.219*0.806 (7)
O12F0.228 (3)0.1562 (15)0.2713 (19)0.092*0.194 (7)
H2F0.30210.13280.29630.138*0.194 (7)
C12F0.259 (5)0.055 (2)0.140 (3)0.120*0.194 (7)
H34F0.35380.04810.17240.180*0.194 (7)
H35F0.25130.04360.06230.180*0.194 (7)
H36F0.20100.01750.17390.180*0.194 (7)
C22F0.215 (3)0.1408 (16)0.1567 (19)0.080*0.194 (7)
H22F0.27360.17940.12170.120*0.194 (7)
C32F0.070 (5)0.154 (3)0.113 (4)0.150*0.194 (7)
H37F0.04450.21010.12500.225*0.194 (7)
H38F0.01270.11700.14890.225*0.194 (7)
H39F0.05700.14240.03490.225*0.194 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S1A0.1140 (15)0.1014 (13)0.0610 (12)0.0102 (11)0.0188 (11)0.0088 (10)
O1A0.0345 (18)0.0431 (16)0.109 (4)0.0002 (14)0.011 (2)0.002 (2)
O2A0.0407 (19)0.0439 (17)0.099 (3)0.0004 (14)0.011 (2)0.0034 (19)
O3A0.047 (2)0.0397 (17)0.102 (3)0.0004 (14)0.022 (2)0.0054 (19)
N1A0.041 (2)0.0417 (19)0.050 (3)0.0014 (16)0.009 (2)0.0027 (18)
N2A0.0286 (18)0.0379 (19)0.062 (3)0.0023 (15)0.0075 (19)0.0002 (19)
C1A0.030 (2)0.039 (2)0.061 (4)0.0011 (18)0.009 (2)0.003 (2)
C2A0.051 (3)0.046 (2)0.045 (4)0.001 (2)0.003 (3)0.001 (2)
C3A0.088 (4)0.060 (3)0.077 (5)0.004 (3)0.018 (4)0.000 (3)
C4A0.116 (6)0.108 (5)0.064 (6)0.010 (5)0.005 (5)0.011 (4)
C5A0.030 (2)0.040 (2)0.056 (4)0.0013 (18)0.006 (2)0.002 (2)
C6A0.036 (2)0.038 (2)0.069 (4)0.0021 (18)0.010 (3)0.002 (2)
C7A0.063 (3)0.056 (3)0.091 (5)0.007 (3)0.012 (3)0.005 (3)
C8A0.039 (3)0.043 (2)0.068 (4)0.0029 (19)0.015 (3)0.002 (2)
S1B0.1044 (14)0.1030 (13)0.0684 (13)0.0003 (11)0.0158 (11)0.0068 (11)
O1B0.0354 (18)0.0421 (16)0.098 (3)0.0005 (14)0.0091 (19)0.0030 (19)
O2B0.050 (2)0.0557 (19)0.068 (3)0.0024 (16)0.001 (2)0.0111 (18)
O3B0.0479 (19)0.0415 (18)0.077 (3)0.0033 (14)0.0141 (19)0.0047 (17)
N1B0.042 (2)0.0383 (19)0.057 (3)0.0043 (15)0.008 (2)0.0017 (19)
N2B0.0316 (19)0.0384 (19)0.070 (3)0.0002 (15)0.004 (2)0.0010 (19)
C1B0.029 (2)0.042 (2)0.061 (4)0.0045 (17)0.005 (2)0.006 (2)
C2B0.046 (3)0.050 (3)0.057 (4)0.001 (2)0.000 (3)0.001 (3)
C3B0.081 (4)0.065 (3)0.070 (5)0.004 (3)0.019 (4)0.006 (3)
C4B0.143 (7)0.118 (6)0.085 (7)0.021 (6)0.017 (6)0.023 (5)
C5B0.033 (2)0.033 (2)0.065 (4)0.0003 (18)0.007 (2)0.001 (2)
C6B0.034 (2)0.035 (2)0.073 (4)0.0008 (18)0.000 (3)0.004 (2)
C7B0.080 (4)0.058 (3)0.065 (5)0.009 (3)0.002 (3)0.002 (3)
C8B0.032 (2)0.049 (2)0.055 (4)0.0028 (19)0.010 (2)0.005 (2)
O1C0.140 (4)0.104 (4)0.060 (3)0.049 (3)0.031 (3)0.010 (3)
C1C0.107 (8)0.175 (11)0.129 (10)0.031 (7)0.038 (7)0.003 (8)
C2C0.117 (11)0.090 (9)0.073 (9)0.014 (5)0.049 (7)0.021 (6)
C3C0.148 (9)0.139 (9)0.086 (8)0.004 (7)0.026 (7)0.016 (7)
O12C0.140 (4)0.104 (4)0.060 (3)0.049 (3)0.031 (3)0.010 (3)
O1D0.094 (3)0.076 (2)0.057 (3)0.000 (2)0.006 (2)0.003 (2)
C1D0.116 (7)0.114 (7)0.110 (8)0.033 (5)0.004 (6)0.019 (6)
C2D0.102 (5)0.080 (4)0.092 (6)0.010 (4)0.002 (5)0.017 (4)
C3D0.135 (7)0.140 (8)0.101 (8)0.007 (6)0.044 (6)0.011 (6)
O1E0.073 (2)0.065 (2)0.065 (3)0.0094 (19)0.014 (2)0.009 (2)
C1E0.116 (7)0.161 (8)0.151 (8)0.049 (6)0.001 (6)0.001 (7)
C2E0.098 (6)0.096 (6)0.085 (7)0.029 (5)0.036 (5)0.013 (5)
C3E0.136 (7)0.125 (7)0.085 (7)0.025 (6)0.053 (5)0.016 (5)
O12E0.073 (2)0.065 (2)0.065 (3)0.0094 (19)0.014 (2)0.009 (2)
O1F0.150 (6)0.067 (3)0.061 (4)0.012 (3)0.040 (4)0.015 (3)
C1F0.108 (6)0.141 (7)0.106 (7)0.016 (6)0.008 (6)0.026 (6)
C2F0.086 (7)0.086 (6)0.064 (6)0.007 (5)0.023 (5)0.007 (5)
C3F0.161 (8)0.160 (8)0.119 (8)0.048 (7)0.028 (7)0.010 (7)
Geometric parameters (Å, º) top
S1A—C4A1.778 (7)C3C—H31C0.9800
S1A—C3A1.785 (6)C3C—H32C0.9800
O1A—C5A1.230 (4)C3C—H33C0.9800
O2A—C8A1.236 (4)C12C—C22C1.501 (9)
O3A—C8A1.274 (4)C12C—H14C0.9800
N1A—C1A1.497 (5)C12C—H15C0.9800
N1A—H1A0.9100C12C—H16C0.9800
N1A—H2A0.9100C22C—C32C1.487 (9)
N1A—H3A0.9100C22C—H22C1.0000
N2A—C5A1.331 (4)C32C—H34C0.9800
N2A—C6A1.458 (5)C32C—H35C0.9800
N2A—H4A0.8800C32C—H36C0.9800
C1A—C2A1.516 (6)O1D—C2D1.449 (6)
C1A—C5A1.527 (5)O1D—H1D0.8504
C1A—H11A1.0000C1D—C2D1.495 (7)
C2A—C3A1.559 (6)C1D—H11D0.9800
C2A—H21A0.9900C1D—H12D0.9800
C2A—H22A0.9900C1D—H13D0.9800
C3A—H31A0.9900C2D—C3D1.480 (8)
C3A—H32A0.9900C2D—H21D1.0000
C4A—H41A0.9800C3D—H31D0.9800
C4A—H42A0.9800C3D—H32D0.9800
C4A—H43A0.9800C3D—H33D0.9800
C6A—C7A1.511 (7)O1E—C2E1.436 (6)
C6A—C8A1.527 (5)O1E—H1E0.8502
C6A—H61A1.0000C1E—C2E1.488 (8)
C7A—H71A0.9800C1E—H11E0.9800
C7A—H72A0.9800C1E—H12E0.9800
C7A—H73A0.9800C1E—H13E0.9800
S1B—C4B1.784 (7)C2E—C3E1.486 (8)
S1B—C3B1.794 (6)C2E—H21E1.0000
O1B—C5B1.232 (4)C3E—H31E0.9800
O2B—C8B1.237 (5)C3E—H32E0.9800
O3B—C8B1.284 (4)C3E—H33E0.9800
N1B—C1B1.500 (5)C12E—C22E1.498 (9)
N1B—H1B0.9100C12E—H14E0.9800
N1B—H2B0.9100C12E—H15E0.9800
N1B—H3B0.9100C12E—H16E0.9800
N2B—C5B1.329 (4)C22E—C32E1.486 (9)
N2B—C6B1.457 (4)C22E—H22E1.0000
N2B—H4B0.8800C32E—H34E0.9800
C1B—C2B1.517 (6)C32E—H35E0.9800
C1B—C5B1.527 (5)C32E—H36E0.9800
C1B—H11B1.0000O1F—C2F1.445 (6)
C2B—C3B1.562 (6)O1F—H1F0.8491
C2B—H21B0.9900C1F—C2F1.505 (8)
C2B—H22B0.9900C1F—H11F0.9800
C3B—H31B0.9900C1F—H12F0.9800
C3B—H32B0.9900C1F—H13F0.9800
C4B—H41B0.9800C2F—C3F1.493 (8)
C4B—H42B0.9800C2F—H21F1.0000
C4B—H43B0.9800C3F—H31F0.9800
C6B—C7B1.510 (7)C3F—H32F0.9800
C6B—C8B1.521 (5)C3F—H33F0.9800
C6B—H61B1.0000C3F—H2F1.1882
C7B—H71B0.9800O12F—C22F1.442 (8)
C7B—H72B0.9800O12F—H2F0.8497
C7B—H73B0.9800C12F—C22F1.500 (9)
O1C—C2C1.443 (6)C12F—H34F0.9800
O1C—H1C0.8511C12F—H35F0.9800
C1C—C2C1.504 (9)C12F—H36F0.9800
C1C—H11C0.9800C22F—C32F1.487 (9)
C1C—H12C0.9800C22F—H22F1.0000
C1C—H13C0.9800C32F—H37F0.9800
C2C—C3C1.490 (9)C32F—H38F0.9800
C2C—H21C1.0000C32F—H39F0.9800
C4A—S1A—C3A101.6 (3)H71B—C7B—H73B109.5
C1A—N1A—H1A109.5H72B—C7B—H73B109.5
C1A—N1A—H2A109.5O2B—C8B—O3B124.2 (4)
H1A—N1A—H2A109.5O2B—C8B—C6B119.8 (4)
C1A—N1A—H3A109.5O3B—C8B—C6B116.0 (4)
H1A—N1A—H3A109.5C2C—O1C—H1C104.2
H2A—N1A—H3A109.5O1C—C2C—C3C106.7 (7)
C5A—N2A—C6A123.2 (3)O1C—C2C—C1C108.4 (7)
C5A—N2A—H4A118.4C3C—C2C—C1C110.7 (8)
C6A—N2A—H4A118.4O1C—C2C—H21C110.3
N1A—C1A—C2A108.2 (3)C3C—C2C—H21C110.3
N1A—C1A—C5A109.7 (3)C1C—C2C—H21C110.3
C2A—C1A—C5A110.8 (4)C22C—C12C—H14C109.5
N1A—C1A—H11A109.3C22C—C12C—H15C109.5
C2A—C1A—H11A109.3H14C—C12C—H15C109.5
C5A—C1A—H11A109.3C22C—C12C—H16C109.5
C1A—C2A—C3A110.3 (4)H14C—C12C—H16C109.5
C1A—C2A—H21A109.6H15C—C12C—H16C109.5
C3A—C2A—H21A109.6C32C—C22C—C12C110.8 (9)
C1A—C2A—H22A109.6C32C—C22C—H22C110.3
C3A—C2A—H22A109.6C12C—C22C—H22C110.4
H21A—C2A—H22A108.1C22C—C32C—H34C109.5
C2A—C3A—S1A113.4 (4)C22C—C32C—H35C109.5
C2A—C3A—H31A108.9H34C—C32C—H35C109.5
S1A—C3A—H31A108.9C22C—C32C—H36C109.5
C2A—C3A—H32A108.9H34C—C32C—H36C109.5
S1A—C3A—H32A108.9H35C—C32C—H36C109.5
H31A—C3A—H32A107.7C2D—O1D—H1D104.3
S1A—C4A—H41A109.5C2D—C1D—H11D109.5
S1A—C4A—H42A109.5C2D—C1D—H12D109.5
H41A—C4A—H42A109.5H11D—C1D—H12D109.5
S1A—C4A—H43A109.5C2D—C1D—H13D109.5
H41A—C4A—H43A109.5H11D—C1D—H13D109.5
H42A—C4A—H43A109.5H12D—C1D—H13D109.5
O1A—C5A—N2A124.0 (3)O1D—C2D—C3D108.1 (6)
O1A—C5A—C1A120.9 (3)O1D—C2D—C1D109.0 (5)
N2A—C5A—C1A115.1 (3)C3D—C2D—C1D113.1 (6)
N2A—C6A—C7A111.4 (4)O1D—C2D—H21D108.9
N2A—C6A—C8A108.8 (3)C3D—C2D—H21D108.9
C7A—C6A—C8A110.8 (4)C1D—C2D—H21D108.9
N2A—C6A—H61A108.6C2D—C3D—H31D109.5
C7A—C6A—H61A108.6C2D—C3D—H32D109.5
C8A—C6A—H61A108.6H31D—C3D—H32D109.5
C6A—C7A—H71A109.5C2D—C3D—H33D109.5
C6A—C7A—H72A109.5H31D—C3D—H33D109.5
H71A—C7A—H72A109.5H32D—C3D—H33D109.5
C6A—C7A—H73A109.5C2E—O1E—H1E104.3
H71A—C7A—H73A109.5O1E—C2E—C3E106.8 (5)
H72A—C7A—H73A109.5O1E—C2E—C1E109.9 (6)
O2A—C8A—O3A124.6 (4)C3E—C2E—C1E113.3 (7)
O2A—C8A—C6A118.8 (3)O1E—C2E—H21E108.9
O3A—C8A—C6A116.5 (3)C3E—C2E—H21E108.9
C4B—S1B—C3B100.2 (3)C1E—C2E—H21E108.9
C1B—N1B—H1B109.5C22E—C12E—H14E109.5
C1B—N1B—H2B109.5C22E—C12E—H15E109.5
H1B—N1B—H2B109.5H14E—C12E—H15E109.5
C1B—N1B—H3B109.5C22E—C12E—H16E109.5
H1B—N1B—H3B109.5H14E—C12E—H16E109.5
H2B—N1B—H3B109.5H15E—C12E—H16E109.5
C5B—N2B—C6B122.8 (3)C32E—C22E—C12E111.7 (10)
C5B—N2B—H4B118.6C32E—C22E—H22E109.5
C6B—N2B—H4B118.6C12E—C22E—H22E109.5
N1B—C1B—C2B107.8 (3)C22E—C32E—H34E109.5
N1B—C1B—C5B109.6 (3)C22E—C32E—H35E109.5
C2B—C1B—C5B110.6 (4)H34E—C32E—H35E109.5
N1B—C1B—H11B109.6C22E—C32E—H36E109.4
C2B—C1B—H11B109.6H34E—C32E—H36E109.5
C5B—C1B—H11B109.6H35E—C32E—H36E109.5
C1B—C2B—C3B110.9 (4)C2F—O1F—H1F104.1
C1B—C2B—H21B109.5O1F—C2F—C3F107.7 (6)
C3B—C2B—H21B109.5O1F—C2F—C1F108.2 (6)
C1B—C2B—H22B109.5C3F—C2F—C1F109.7 (7)
C3B—C2B—H22B109.5O1F—C2F—H21F110.4
H21B—C2B—H22B108.1C3F—C2F—H21F110.4
C2B—C3B—S1B112.7 (4)C1F—C2F—H21F110.4
C2B—C3B—H31B109.1C2F—C3F—H2F112.9
S1B—C3B—H31B109.1H31F—C3F—H2F33.9
C2B—C3B—H32B109.1H32F—C3F—H2F131.7
S1B—C3B—H32B109.1H33F—C3F—H2F77.0
H31B—C3B—H32B107.8C22F—O12F—H2F104.3
S1B—C4B—H41B109.5C22F—C12F—H34F109.5
S1B—C4B—H42B109.5C22F—C12F—H35F109.5
H41B—C4B—H42B109.5H34F—C12F—H35F109.5
S1B—C4B—H43B109.5C22F—C12F—H36F109.5
H41B—C4B—H43B109.5H34F—C12F—H36F109.5
H42B—C4B—H43B109.5H35F—C12F—H36F109.5
O1B—C5B—N2B123.9 (3)O12F—C22F—C32F107.4 (9)
O1B—C5B—C1B120.8 (3)O12F—C22F—C12F108.3 (9)
N2B—C5B—C1B115.2 (3)C32F—C22F—C12F111.6 (10)
N2B—C6B—C7B112.2 (4)O12F—C22F—H22F109.8
N2B—C6B—C8B108.6 (3)C32F—C22F—H22F109.8
C7B—C6B—C8B113.3 (4)C12F—C22F—H22F109.8
N2B—C6B—H61B107.5C22F—C32F—H37F109.5
C7B—C6B—H61B107.5C22F—C32F—H38F109.5
C8B—C6B—H61B107.5H37F—C32F—H38F109.5
C6B—C7B—H71B109.5C22F—C32F—H39F109.5
C6B—C7B—H72B109.5H37F—C32F—H39F109.5
H71B—C7B—H72B109.5H38F—C32F—H39F109.5
C6B—C7B—H73B109.5
N1A—C1A—C2A—C3A169.9 (4)N1B—C1B—C2B—C3B171.4 (4)
C5A—C1A—C2A—C3A69.7 (5)C5B—C1B—C2B—C3B68.7 (5)
C1A—C2A—C3A—S1A178.4 (4)C1B—C2B—C3B—S1B176.0 (4)
C4A—S1A—C3A—C2A69.8 (5)C4B—S1B—C3B—C2B69.3 (5)
C6A—N2A—C5A—O1A4.5 (8)C6B—N2B—C5B—O1B4.9 (9)
C6A—N2A—C5A—C1A174.5 (4)C6B—N2B—C5B—C1B171.5 (4)
N1A—C1A—C5A—O1A49.2 (6)N1B—C1B—C5B—O1B42.1 (6)
C2A—C1A—C5A—O1A70.3 (6)C2B—C1B—C5B—O1B76.6 (6)
N1A—C1A—C5A—N2A131.8 (4)N1B—C1B—C5B—N2B141.3 (4)
C2A—C1A—C5A—N2A108.7 (5)C2B—C1B—C5B—N2B99.9 (5)
C5A—N2A—C6A—C7A79.1 (6)C5B—N2B—C6B—C7B93.9 (6)
C5A—N2A—C6A—C8A158.5 (5)C5B—N2B—C6B—C8B140.1 (5)
N2A—C6A—C8A—O2A13.2 (7)N2B—C6B—C8B—O2B11.5 (6)
C7A—C6A—C8A—O2A109.5 (5)C7B—C6B—C8B—O2B136.9 (5)
N2A—C6A—C8A—O3A170.1 (5)N2B—C6B—C8B—O3B168.7 (4)
C7A—C6A—C8A—O3A67.1 (6)C7B—C6B—C8B—O3B43.4 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1A···O3B0.911.882.734 (5)155
N1A—H2A···O3Ai0.911.802.706 (5)176
N1A—H3A···O1F0.911.962.790 (7)151
N2A—H4A···O1Bii0.882.613.410 (5)151
C1A—H11B···O1Bii1.002.183.176 (5)171
N1B—H1B···O2Aiii0.911.832.735 (5)175
N1B—H2B···O3Biv0.911.972.813 (5)153
N1B—H3B···O1C0.911.872.772 (6)174
N2B—H4B···O1Ai0.882.193.044 (5)165
C1B—H11A···O1Ai1.002.403.307 (5)150
O1C—H1C···O1Diii0.851.912.734 (6)163
O1D—H1D···O1Eii0.851.922.768 (6)176
O1E—H1E···O2B0.851.822.666 (5)177
O1F—H1F···O1E0.852.092.748 (7)133
Symmetry codes: (i) x, y+1/2, z+1; (ii) x+1, y1/2, z+1; (iii) x, y+1, z; (iv) x+1, y+1/2, z+1.

Experimental details

Crystal data
Chemical formulaC8H16N2O3S·2C3H8O
Mr340.48
Crystal system, space groupMonoclinic, P21
Temperature (K)150
a, b, c (Å)9.9277 (2), 16.4556 (3), 12.4895 (2)
β (°) 97.594 (1)
V3)2022.47 (6)
Z4
Radiation typeMo Kα
µ (mm1)0.18
Crystal size (mm)0.80 × 0.48 × 0.01
Data collection
DiffractometerSiemens SMART CCD
diffractometer
Absorption correctionEmpirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.865, 0.998
No. of measured, independent and
observed [I > 2σ(I)] reflections
14839, 6911, 4437
Rint0.093
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.078, 0.202, 1.01
No. of reflections6911
No. of parameters448
No. of restraints198
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.53, 0.30
Absolute structureFlack (1983), 3230 Friedel pairs
Absolute structure parameter0.01 (16)

Computer programs: SMART (Siemens, 1995), SAINT (Siemens, 1995), SIR92 (Altomare et al., 1994), SHELXTL (Sheldrick, 1997).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1A···O3B0.911.882.734 (5)155
N1A—H2A···O3Ai0.911.802.706 (5)176
N1A—H3A···O1F0.911.962.790 (7)151
N2A—H4A···O1Bii0.882.613.410 (5)151
C1A—H11B···O1Bii1.002.183.176 (5)171
N1B—H1B···O2Aiii0.911.832.735 (5)175
N1B—H2B···O3Biv0.911.972.813 (5)153
N1B—H3B···O1C0.911.872.772 (6)174
N2B—H4B···O1Ai0.882.193.044 (5)165
C1B—H11A···O1Ai1.002.403.307 (5)150
O1C—H1C···O1Diii0.851.912.734 (6)163
O1D—H1D···O1Eii0.851.922.768 (6)176
O1E—H1E···O2B0.851.822.666 (5)177
O1F—H1F···O1E0.852.092.748 (7)133
Symmetry codes: (i) x, y+1/2, z+1; (ii) x+1, y1/2, z+1; (iii) x, y+1, z; (iv) x+1, y+1/2, z+1.
 

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