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The antibiotic cephalexin [systematic name: D-7-(2-amino-2-phenyl­acet­amido)-3-methyl-8-oxo-5-thia-1-aza­bi­cyclo­[4.2.0]oct-2-ene-2-carboxyl­ic acid] forms a range of isomorphic solvates, with the maximum hydration state of two water mol­ecules formed only at high relative humidities. The water content of the structure reported here (C16H17N3O4S·1.9H2O) falls just short of this configuration, having three independent cephalexin mol­ecules, one of which is disordered, and 5.72 observed water mol­ecules in the asymmetric unit. The facile nature of the cephalexin solvation/desolvation process is found to be facilitated by a complex channel structure, which allows free movement of solvent in the crystallographic a and b directions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270103022649/bm1543sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270103022649/bm1543Isup2.hkl
Contains datablock I

CCDC reference: 226139

Comment top

The cephalosporin derivative cephalexin (CEX) is an antibiotic useful for treating a variety of infections, including those of the respiratory tract, of the skin and of other soft tissues. The characterization of the solid-state properties of CEX has, however, been hampered by uncertainty over the exact nature of its hydration behaviour. CEX can form a range of hydrates in the solid state, all with essentially identical unit cells, and has thus been identified as part of the class of compounds known as isomorphic desolvates (Stephenson et al., 1998). Indeed, CEX is known to go further and reversibly replaces water with other small, polar, solvent molecules (Pfeiffer et al., 1970). Powder diffraction shows that the isomorphic solvates have similar unit-cell dimensions but, despite their crystallographic similarities, their commercially important physical properties (such as their solubilities and dehydration behaviour) vary considerably. Despite considerable interest in CEX, no single-crystal structure determination had previously been achieved, and so the structural basis of its ready solvation/desolvation process remained unknown. However, we have overcome the problems of small crystal size and loss of (single) crystallinity upon facile dehydration by utilizing careful sample preparation methods (see experimental section) and the extra intensity of synchrotron radiation to report here the first crystal structure of any CEX hydrate, that of CEX·1.9H2O, (I).

The asymmetic unit of (I) was found to contain three CEX molecules and, spread over ten sites, 5.72 water molecules. The three crystallographically independant molecules of CEX (Fig. 1) were found to exist in the zwitterionic form, with no significant differences in their bond lengths or angles. One CEX molecule is disordered, and so its geometric parameters are omitted from Table 2. There is some flexibility in the amide backbone, with the O—C—C—N(H3) torsion angles ranging from 27.3 (6) to 44.5 (6) °. The geometry of the related species cefadroxil (Shin & Cho, 1992) has a similar conformation, fitting within the range found here for CEX, as does CEX complexed with β- napthol (Kemperman et al., 1999), although here the amide backbone is more eclipsed (equivalent angle 16.2 °).

That the stochiometrically exact dihydrate is not found is unsurprizing, given the steep gradient observed by Stephenson et al. (1998) in the moisture adsorption isotherms of CEX. Only above 70% relative humidity does CEX begin to approach a genuine dihydrate. The structural basis of the ready transportation of water is seen in Fig. 2. The water molecules lie in a distinct channel, which zigzags along the a direction. The channel displays distinct and repeating narrow and wide sections along its length, with the narrower section (containing atoms O17 and O19) centred about a = 0 and 1/2, and the wider section about a = 0.25 and 0.75. These wide and narrow sections extend seperately along the b direction, creating a grid of channels extending throughout the ab plane. Only atom O15 appears to lie outside the channels running along b. With solvent transport blocked only in the c direction, it can easily be seen how different CEX hydrates can have similar unit cells. The water sites exist as pairs with a total occupancy of 1, except for atom O13 in the wide section, which is the only fully occupied site, and the uniquely positioned atom O15. This complex arrangement with fluctuating void spaces must have a considerable effect on the dehydration behaviour of CEX. Interpreting the hydrogen-bonding behaviour is difficult, as the H atoms of the water molecules could not be reliably placed. Table 3 shows only hydrogen-bonding involving N—H donors, but it should be remembered that there must be considerable bonding via O—H donors as well. Within these limitations, some interesting points can be raised. Firstly, only those water sites already highlighted (the narrow channel sites O15, O17 and O19, and the wholly occupied site O13) form hydrogen-bonds with amine units. It is tempting to suggest that loss of the other water molecules should be favoured, leaving, as is in fact found under ambient conditions, a compound that is approximately monohydrate. There is also a sharp change in the gradient of Stephenson's moisture adsorption isotherm, corresponding to a psuedo-stable partial hydrate (CEX.nH2O, with n = 0.25–0.35). This could be explained by further site selective stripping of water to leave perhaps only the completely occupied site O13 (giving CEX·0.33H2O) or the unique site O15 (giving CEX·0.24H2O).

Experimental top

Crystalline CEX was obtained by suspending small amounts of technical grade CEX powder in a saturated aqueous solution and allowing slow evaporation to take place at room temperature. The crystals were isolated from solution, blotted free of liquid, packed in well sealed containers, with a minimum of void space, and stored at 277 K in a refrigirator to maintain their stochiometry for the purpose of analysis. Thermogravimetric analysis showed the presence of 9.0% (w/w) water (cf. 9.4% required for CEX·2H2O) and microanalytical data also suggested the presence of approximately two water molecules. Exposure to ambient laboratory conditions led to rapid loss of water (giving CEX·H2O). Samples were transported to the SRS in sealed containers packed with dry ice. Prior to data collection, they were exposed to a humidity of more than 75% for 2 h to ensure maximum hydration.

Refinement top

Disorder in one molecule of CEX was modelled using isotropic C atoms split over two sites with a total occupancy of 1. The H atoms of the water molecules could not be positioned reliably and were omitted from the final model. All other H atoms were placed in idealized positions and refined in riding mode (methyl and NH3 H orientations were obtained by refining a torsion angle, and were given Uiso values of 1.5Ueq of the parent atom; for other H atoms, Uiso(H) was 1.2Ueq [N—H = 0.91 Å (NH3), N—H = 0.88 Å (NH), C—H = 0.98 Å (CH3), C—H = 0.99 (CH2), C—H = 1.00 (CH)Å and C—H = 0.95 Å (sp2CH). The absolute configuration could not be determined from the intensity data and is therefore based on the known geometry of cephalosporins (Kemperman et al., 1999).

Computing details top

Data collection: SMART (Bruker, 1995); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1974); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. A displacement ellipsoid plot of one of the three unique molecules of CEX in the asymmetric unit. Non-H atoms are shown as 50% probability ellipsoids and H atoms as small spheres of arbitary size.
[Figure 2] Fig. 2. The crystal packing of (I), viewed along the b axis.
(I) top
Crystal data top
C16H17N3O4S·1.9H2OF(000) = 2414
Mr = 381.88Dx = 1.404 Mg m3
Monoclinic, C2Synchrotron radiation, λ = 0.6891 Å
a = 31.548 (2) ÅCell parameters from 14822 reflections
b = 11.8574 (9) Åθ = 2.1–27.5°
c = 15.6654 (11) ŵ = 0.22 mm1
β = 112.364 (2)°T = 150 K
V = 5419.3 (7) Å3Needle, colourless
Z = 120.20 × 0.05 × 0.01 mm
Data collection top
Bruker AXS SMART CCD
diffractometer
10703 independent reflections
Radiation source: Daresbury SRS Station 9.88136 reflections with I > 2σ(I)
Si 111 monochromatorRint = 0.047
Detector resolution: 8.192 pixels mm-1θmax = 26.0°, θmin = 2.1°
ω rotation with narrow frames scansh = 2140
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
k = 1415
Tmin = 0.96, Tmax = 1.00l = 1919
14822 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.074H-atom parameters constrained
wR(F2) = 0.193 w = 1/[σ2(Fo2) + (0.1215P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.001
10703 reflectionsΔρmax = 0.58 e Å3
717 parametersΔρmin = 0.47 e Å3
1 restraintAbsolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.21 (10)
Crystal data top
C16H17N3O4S·1.9H2OV = 5419.3 (7) Å3
Mr = 381.88Z = 12
Monoclinic, C2Synchrotron radiation, λ = 0.6891 Å
a = 31.548 (2) ŵ = 0.22 mm1
b = 11.8574 (9) ÅT = 150 K
c = 15.6654 (11) Å0.20 × 0.05 × 0.01 mm
β = 112.364 (2)°
Data collection top
Bruker AXS SMART CCD
diffractometer
10703 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
8136 reflections with I > 2σ(I)
Tmin = 0.96, Tmax = 1.00Rint = 0.047
14822 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.074H-atom parameters constrained
wR(F2) = 0.193Δρmax = 0.58 e Å3
S = 1.01Δρmin = 0.47 e Å3
10703 reflectionsAbsolute structure: Flack (1983)
717 parametersAbsolute structure parameter: 0.21 (10)
1 restraint
Special details top

Experimental. Bruker's SAINT software was used to integrate the data. As this

is a synchrotron experiment the main effect is incident beam

decay. The correction for this is bundled with the small effects

for absorption and sample decay. The diffrn_standards_decay_%

entry is thus large as it is mainly due to decay of the

incident beam.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
S10.30860 (4)0.01130 (11)0.40610 (8)0.0236 (3)
O10.19989 (14)0.3407 (4)0.2921 (3)0.0390 (10)
O20.23321 (12)0.3796 (3)0.4426 (2)0.0301 (8)
O30.16511 (11)0.1020 (3)0.3409 (2)0.0261 (8)
O40.19007 (12)0.2541 (3)0.2256 (2)0.0298 (8)
N10.23724 (13)0.1280 (4)0.3328 (3)0.0212 (8)
N20.21788 (14)0.1343 (4)0.3462 (3)0.0228 (9)
H20.22670.12750.40640.027*
N30.19169 (14)0.4254 (4)0.3497 (3)0.0266 (9)
H3A0.20250.48670.38650.040*
H3B0.16580.40000.35590.040*
H3C0.18520.44490.28990.040*
C10.33549 (16)0.1257 (4)0.4209 (3)0.0223 (10)
H1A0.34680.13690.37060.027*
H1B0.36250.12540.47980.027*
C20.30577 (16)0.2263 (4)0.4216 (3)0.0182 (9)
C30.26017 (15)0.2251 (4)0.3810 (3)0.0177 (9)
C40.25885 (16)0.0312 (4)0.3079 (3)0.0223 (10)
H40.26510.04290.25050.027*
C50.21423 (16)0.0355 (4)0.2917 (3)0.0199 (10)
H50.19640.05010.22470.024*
C60.19767 (16)0.0737 (4)0.3254 (3)0.0211 (10)
C70.33213 (18)0.3275 (5)0.4670 (4)0.0308 (12)
H7A0.31110.39070.46000.046*
H7B0.34890.31190.53270.046*
H7C0.35390.34680.43830.046*
C80.22826 (16)0.3217 (4)0.3714 (3)0.0224 (10)
C90.20835 (16)0.2367 (4)0.3085 (3)0.0231 (10)
C100.22680 (16)0.3353 (4)0.3772 (3)0.0227 (10)
H100.23200.30900.44100.027*
C110.27147 (16)0.3723 (4)0.3730 (3)0.0245 (10)
C120.31180 (19)0.3494 (5)0.4463 (4)0.0365 (13)
H120.31090.31240.49940.044*
C130.35360 (19)0.3796 (6)0.4434 (5)0.0454 (16)
H130.38130.36330.49400.054*
C140.3548 (2)0.4344 (6)0.3654 (5)0.0437 (16)
H140.38320.45730.36330.052*
C150.3152 (2)0.4547 (6)0.2927 (4)0.0403 (14)
H150.31610.48940.23880.048*
C160.27354 (19)0.4255 (5)0.2961 (4)0.0293 (11)
H160.24600.44210.24510.035*
S20.03365 (4)0.94752 (12)0.34163 (9)0.0296 (3)
O50.11181 (12)1.3454 (3)0.3529 (2)0.0256 (8)
O60.06821 (16)1.3330 (3)0.2033 (3)0.0381 (10)
O70.11226 (11)1.0941 (3)0.1899 (2)0.0234 (7)
O80.02084 (12)0.7409 (3)0.1037 (2)0.0285 (8)
N40.05036 (13)1.1100 (3)0.2383 (3)0.0192 (8)
N50.07413 (13)0.8519 (3)0.2084 (3)0.0208 (8)
H5A0.10090.85460.25470.025*
N60.07344 (15)0.5556 (4)0.1525 (3)0.0263 (9)
H6A0.07530.48870.18210.039*
H6B0.09370.55590.12390.039*
H6C0.04450.56490.10970.039*
C170.02042 (19)1.0766 (5)0.3875 (4)0.0305 (12)
H17A0.01321.08790.36000.037*
H17B0.02921.06690.45480.037*
C180.04298 (16)1.1819 (5)0.3720 (3)0.0279 (11)
C190.05790 (15)1.1967 (4)0.3033 (3)0.0193 (9)
C200.04900 (15)0.9538 (4)0.1746 (3)0.0183 (9)
H200.02980.94920.10710.022*
C210.02259 (15)1.0082 (4)0.2292 (3)0.0201 (9)
H210.01071.01980.19160.024*
C220.07791 (16)1.0618 (4)0.1990 (3)0.0192 (10)
C230.04504 (18)1.2751 (5)0.4392 (4)0.0332 (13)
H23A0.05791.34320.42300.050*
H23B0.06451.25140.50190.050*
H23C0.01411.29120.43640.050*
C240.08137 (16)1.3010 (4)0.2851 (3)0.0209 (10)
C250.05692 (16)0.7514 (4)0.1697 (3)0.0194 (9)
C260.08443 (16)0.6491 (4)0.2203 (3)0.0215 (10)
H260.11800.66620.24410.026*
C270.06980 (17)0.6227 (4)0.3003 (3)0.0235 (10)
C280.10077 (18)0.6407 (5)0.3891 (4)0.0308 (12)
H280.13130.66260.39970.037*
C290.0872 (2)0.6267 (6)0.4630 (4)0.0366 (13)
H290.10800.64190.52420.044*
C300.0434 (2)0.5905 (7)0.4470 (4)0.0467 (17)
H300.03440.57800.49770.056*
C310.0120 (2)0.5721 (7)0.3578 (5)0.0504 (17)
H310.01840.54910.34740.060*
C320.02550 (19)0.5876 (5)0.2843 (4)0.0326 (12)
H320.00450.57430.22300.039*
S30.38897 (8)0.35790 (15)0.18246 (13)0.0574 (5)
O90.3285 (3)0.0229 (5)0.0085 (5)0.085 (2)
O100.3989 (3)0.0226 (5)0.0104 (6)0.094 (2)
O110.37462 (15)0.2227 (4)0.0865 (3)0.0417 (10)
O120.45530 (12)0.5732 (3)0.0199 (2)0.0241 (7)
N70.40532 (19)0.2020 (4)0.0744 (4)0.0387 (12)
N80.39530 (14)0.4642 (4)0.0118 (3)0.0246 (9)
H80.36560.46290.00140.030*
N90.39751 (17)0.7552 (4)0.0509 (3)0.0310 (10)
H9A0.42800.75110.03910.047*
H9B0.39090.82400.03340.047*
H9C0.38130.74530.11240.047*
C330.3774 (4)0.2175 (9)0.2268 (8)0.035 (3)*0.58 (2)
H33A0.40530.19590.28030.042*0.58 (2)
H33B0.35260.22880.25010.042*0.58 (2)
C340.3641 (5)0.1190 (10)0.1606 (10)0.040 (3)*0.58 (2)
C350.3831 (3)0.1136 (5)0.1007 (6)0.057 (2)
C360.4257 (2)0.3037 (5)0.1282 (4)0.0367 (13)
H360.45830.29330.17170.044*
C370.42095 (18)0.3599 (5)0.0363 (4)0.0275 (11)
H370.45120.36600.02970.033*
C380.39532 (19)0.2533 (5)0.0092 (4)0.0292 (12)
C390.3428 (5)0.0277 (11)0.1970 (9)0.044 (3)*0.58 (2)
H39A0.35070.04590.17870.066*0.58 (2)
H39B0.30940.03700.17150.066*0.58 (2)
H39C0.35440.03240.26440.066*0.58 (2)
C400.3694 (4)0.0133 (7)0.0344 (7)0.073 (3)
C410.41541 (17)0.5627 (4)0.0085 (3)0.0221 (10)
C420.38497 (18)0.6656 (4)0.0017 (3)0.0239 (10)
H420.35200.64450.03120.029*
C430.39311 (17)0.7045 (4)0.0996 (3)0.0252 (11)
C440.3612 (2)0.6805 (5)0.1375 (4)0.0355 (13)
H440.33380.64110.10280.043*
C450.3697 (3)0.7153 (6)0.2279 (5)0.0464 (16)
H450.34790.70040.25490.056*
C460.4090 (2)0.7702 (6)0.2768 (4)0.0450 (17)
H460.41500.79060.33900.054*
C470.4405 (2)0.7975 (7)0.2390 (4)0.0504 (18)
H470.46700.84040.27300.060*
C480.43266 (18)0.7610 (6)0.1501 (4)0.0372 (14)
H480.45490.77520.12410.045*
C1000.3646 (8)0.0353 (16)0.2328 (15)0.053 (5)*0.42 (2)
C1010.3825 (5)0.1304 (10)0.1922 (9)0.018 (3)*0.42 (2)
C1020.3993 (6)0.2337 (14)0.2559 (11)0.035 (4)*0.42 (2)
O130.29840 (15)0.4602 (5)0.0604 (3)0.0522 (12)
O140.23811 (19)0.7581 (5)0.1559 (4)0.050 (2)0.860 (15)
O150.1647 (2)0.5017 (5)0.1667 (4)0.043 (2)0.716 (18)
O160.2499 (2)0.6052 (7)0.0212 (4)0.063 (3)0.793 (15)
O210.2440 (8)0.475 (2)0.0549 (17)0.058 (9)*0.207 (15)
O220.2516 (8)0.667 (2)0.1584 (17)0.027 (9)*0.140 (15)
O170.0119 (2)0.2744 (6)0.0345 (4)0.0251 (15)*0.50
O180.2201 (3)0.2776 (8)0.0743 (6)0.063 (3)*0.67 (2)
O190.4856 (3)0.0100 (8)0.0342 (6)0.047 (2)*0.50
O200.2498 (8)0.236 (2)0.1159 (16)0.089 (9)*0.33 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0202 (5)0.0229 (6)0.0279 (6)0.0049 (5)0.0092 (5)0.0042 (5)
O10.041 (2)0.032 (2)0.035 (2)0.0101 (18)0.0039 (18)0.0117 (18)
O20.036 (2)0.025 (2)0.0324 (19)0.0045 (16)0.0164 (16)0.0032 (16)
O30.0230 (17)0.0230 (19)0.0338 (19)0.0037 (14)0.0125 (15)0.0001 (15)
O40.038 (2)0.021 (2)0.0270 (19)0.0086 (15)0.0080 (16)0.0035 (15)
N10.0215 (19)0.026 (2)0.0155 (18)0.0044 (17)0.0057 (15)0.0022 (16)
N20.029 (2)0.020 (2)0.020 (2)0.0002 (17)0.0097 (17)0.0039 (16)
N30.025 (2)0.018 (2)0.041 (2)0.0006 (16)0.0178 (19)0.0045 (18)
C10.020 (2)0.024 (3)0.022 (2)0.0020 (19)0.0067 (18)0.002 (2)
C20.025 (2)0.021 (3)0.010 (2)0.0033 (18)0.0079 (17)0.0026 (18)
C30.020 (2)0.013 (2)0.021 (2)0.0005 (17)0.0090 (18)0.0010 (18)
C40.025 (2)0.025 (3)0.014 (2)0.0037 (19)0.0033 (18)0.0016 (19)
C50.028 (2)0.020 (3)0.012 (2)0.0032 (19)0.0084 (18)0.0036 (17)
C60.022 (2)0.022 (3)0.016 (2)0.0037 (19)0.0028 (18)0.0001 (18)
C70.027 (3)0.025 (3)0.039 (3)0.001 (2)0.012 (2)0.002 (2)
C80.027 (2)0.015 (2)0.030 (3)0.002 (2)0.015 (2)0.002 (2)
C90.022 (2)0.023 (3)0.028 (3)0.007 (2)0.014 (2)0.003 (2)
C100.026 (2)0.024 (3)0.019 (2)0.003 (2)0.0096 (19)0.000 (2)
C110.027 (2)0.020 (3)0.030 (3)0.003 (2)0.015 (2)0.008 (2)
C120.036 (3)0.032 (3)0.036 (3)0.003 (2)0.008 (2)0.011 (3)
C130.025 (3)0.043 (4)0.061 (4)0.004 (3)0.007 (3)0.017 (3)
C140.035 (3)0.038 (4)0.071 (4)0.010 (3)0.035 (3)0.023 (3)
C150.047 (3)0.037 (3)0.052 (4)0.007 (3)0.036 (3)0.013 (3)
C160.037 (3)0.026 (3)0.026 (3)0.001 (2)0.013 (2)0.004 (2)
S20.0338 (7)0.0290 (8)0.0293 (7)0.0066 (6)0.0156 (5)0.0074 (6)
O50.0277 (18)0.025 (2)0.0245 (17)0.0069 (14)0.0109 (14)0.0064 (15)
O60.063 (3)0.016 (2)0.030 (2)0.0086 (18)0.0128 (19)0.0013 (16)
O70.0220 (17)0.0199 (19)0.0287 (18)0.0027 (14)0.0102 (14)0.0024 (14)
O80.036 (2)0.0179 (19)0.0247 (18)0.0006 (15)0.0038 (15)0.0047 (15)
N40.024 (2)0.011 (2)0.0195 (19)0.0053 (15)0.0048 (16)0.0008 (15)
N50.022 (2)0.013 (2)0.023 (2)0.0015 (16)0.0048 (16)0.0007 (17)
N60.032 (2)0.014 (2)0.040 (2)0.0017 (17)0.022 (2)0.0018 (18)
C170.037 (3)0.039 (3)0.026 (3)0.006 (2)0.023 (2)0.001 (2)
C180.022 (2)0.040 (3)0.019 (2)0.002 (2)0.0058 (19)0.002 (2)
C190.022 (2)0.021 (3)0.015 (2)0.0031 (19)0.0081 (18)0.0032 (18)
C200.026 (2)0.011 (2)0.020 (2)0.0035 (18)0.0113 (18)0.0023 (18)
C210.022 (2)0.019 (2)0.021 (2)0.004 (2)0.0096 (18)0.002 (2)
C220.029 (3)0.010 (2)0.016 (2)0.0014 (18)0.0056 (19)0.0018 (17)
C230.025 (3)0.049 (4)0.025 (3)0.004 (2)0.009 (2)0.009 (2)
C240.028 (2)0.015 (2)0.021 (2)0.0036 (19)0.0108 (19)0.0039 (19)
C250.026 (2)0.016 (2)0.018 (2)0.0041 (19)0.0096 (19)0.0036 (18)
C260.023 (2)0.016 (2)0.028 (2)0.0036 (18)0.013 (2)0.003 (2)
C270.029 (2)0.014 (2)0.030 (3)0.0018 (19)0.015 (2)0.004 (2)
C280.029 (3)0.031 (3)0.035 (3)0.003 (2)0.015 (2)0.003 (2)
C290.042 (3)0.049 (4)0.019 (2)0.010 (3)0.011 (2)0.000 (2)
C300.054 (4)0.064 (5)0.032 (3)0.007 (3)0.028 (3)0.010 (3)
C310.041 (3)0.061 (5)0.056 (4)0.006 (3)0.026 (3)0.009 (4)
C320.037 (3)0.035 (3)0.025 (3)0.001 (2)0.011 (2)0.002 (2)
S30.1130 (16)0.0310 (9)0.0562 (10)0.0305 (10)0.0636 (11)0.0138 (8)
O90.111 (5)0.060 (4)0.116 (5)0.016 (4)0.078 (4)0.008 (4)
O100.128 (5)0.027 (3)0.172 (7)0.002 (3)0.108 (6)0.010 (4)
O110.053 (2)0.024 (2)0.060 (3)0.0029 (19)0.035 (2)0.007 (2)
O120.0315 (19)0.0180 (18)0.0278 (18)0.0012 (14)0.0168 (15)0.0006 (14)
N70.064 (3)0.017 (2)0.058 (3)0.010 (2)0.048 (3)0.010 (2)
N80.028 (2)0.023 (2)0.028 (2)0.0052 (18)0.0168 (17)0.0029 (18)
N90.059 (3)0.016 (2)0.022 (2)0.007 (2)0.020 (2)0.0041 (18)
C350.095 (5)0.020 (3)0.094 (5)0.022 (3)0.079 (5)0.022 (3)
C360.058 (4)0.025 (3)0.037 (3)0.011 (3)0.028 (3)0.007 (2)
C370.033 (3)0.026 (3)0.031 (3)0.002 (2)0.020 (2)0.005 (2)
C380.039 (3)0.022 (3)0.041 (3)0.000 (2)0.031 (3)0.006 (2)
C400.122 (7)0.035 (4)0.108 (7)0.011 (5)0.097 (6)0.017 (5)
C410.033 (3)0.023 (3)0.014 (2)0.002 (2)0.013 (2)0.0000 (19)
C420.034 (3)0.018 (3)0.021 (2)0.009 (2)0.011 (2)0.0017 (19)
C430.033 (3)0.023 (3)0.020 (2)0.008 (2)0.010 (2)0.001 (2)
C440.043 (3)0.033 (3)0.039 (3)0.000 (3)0.026 (3)0.004 (3)
C450.068 (4)0.041 (4)0.047 (4)0.003 (3)0.040 (3)0.003 (3)
C460.055 (4)0.059 (5)0.017 (3)0.019 (3)0.009 (3)0.005 (3)
C470.036 (3)0.071 (5)0.031 (3)0.012 (3)0.003 (3)0.025 (3)
C480.026 (3)0.060 (4)0.026 (3)0.000 (3)0.010 (2)0.019 (3)
O130.045 (2)0.056 (3)0.057 (3)0.002 (2)0.021 (2)0.006 (2)
O140.058 (3)0.054 (4)0.041 (3)0.006 (3)0.023 (3)0.008 (3)
O150.056 (4)0.025 (3)0.036 (3)0.009 (3)0.005 (3)0.006 (3)
O160.061 (4)0.076 (5)0.061 (4)0.012 (4)0.032 (3)0.018 (4)
Geometric parameters (Å, º) top
S1—C41.802 (5)C23—H23A0.9800
S1—C11.807 (5)C23—H23B0.9800
O1—C81.244 (6)C23—H23C0.9800
O2—C81.268 (6)C25—C261.526 (7)
O3—C61.190 (6)C26—C271.524 (7)
O4—C91.221 (6)C26—H261.0000
N1—C61.370 (7)C27—C281.379 (8)
N1—C31.415 (6)C27—C321.387 (8)
N1—C41.462 (6)C28—C291.389 (8)
N2—C91.333 (7)C28—H280.9500
N2—C51.428 (6)C29—C301.377 (9)
N2—H20.8800C29—H290.9500
N3—C101.480 (7)C30—C311.388 (10)
N3—H3A0.9100C30—H300.9500
N3—H3B0.9100C31—C321.384 (8)
N3—H3C0.9100C31—H310.9500
C1—C21.519 (7)C32—H320.9500
C1—H1A0.9900S3—C361.798 (6)
C1—H1B0.9900S3—C1021.820 (15)
C2—C31.333 (6)S3—C331.892 (11)
C2—C71.478 (7)O9—C401.271 (12)
C3—C81.495 (7)O10—C401.207 (9)
C4—C51.549 (7)O11—C381.192 (7)
C4—H41.0000O12—C411.208 (6)
C5—C61.561 (7)N7—C381.368 (8)
C5—H51.0000N7—C351.407 (8)
C7—H7A0.9800N7—C361.472 (8)
C7—H7B0.9800N8—C411.339 (7)
C7—H7C0.9800N8—C371.448 (7)
C9—C101.545 (7)N8—H80.8800
C10—C111.501 (7)N9—C421.487 (7)
C10—H101.0000N9—H9A0.9100
C11—C121.378 (8)N9—H9B0.9100
C11—C161.384 (7)N9—H9C0.9100
C12—C131.384 (9)C33—C341.512 (17)
C12—H120.9500C33—H33A0.9900
C13—C141.397 (10)C33—H33B0.9900
C13—H130.9500C34—C351.294 (13)
C14—C151.354 (10)C34—C391.496 (17)
C14—H140.9500C35—C1011.455 (14)
C15—C161.378 (8)C35—C401.530 (13)
C15—H150.9500C36—C371.541 (8)
C16—H160.9500C36—H361.0000
S2—C171.806 (6)C37—C381.523 (8)
S2—C211.809 (5)C37—H371.0000
O5—C241.246 (6)C39—H39A0.9800
O6—C241.246 (6)C39—H39B0.9800
O7—C221.208 (6)C39—H39C0.9800
O8—C251.219 (6)C41—C421.531 (7)
N4—C221.367 (6)C42—C431.527 (7)
N4—C191.403 (6)C42—H421.0000
N4—C211.466 (6)C43—C481.371 (8)
N5—C251.354 (6)C43—C441.381 (8)
N5—C201.432 (6)C44—C451.399 (9)
N5—H5A0.8800C44—H440.9500
N6—C261.482 (7)C45—C461.350 (10)
N6—H6A0.9100C45—H450.9500
N6—H6B0.9100C46—C471.374 (10)
N6—H6C0.9100C46—H460.9500
C17—C181.502 (8)C47—C481.388 (8)
C17—H17A0.9900C47—H470.9500
C17—H17B0.9900C48—H480.9500
C18—C191.340 (7)C100—C1011.51 (2)
C18—C231.511 (8)C101—C1021.54 (2)
C19—C241.523 (7)O14—O221.15 (3)
C20—C221.533 (7)O16—O211.67 (3)
C20—C211.544 (6)O17—O17i1.056 (12)
C20—H201.0000O18—O201.04 (2)
C21—H211.0000O19—O19ii1.646 (18)
C4—S1—C194.1 (2)N4—C22—C2092.4 (4)
C6—N1—C3133.8 (4)C18—C23—H23A109.5
C6—N1—C496.3 (4)C18—C23—H23B109.5
C3—N1—C4125.8 (4)H23A—C23—H23B109.5
C9—N2—C5121.9 (4)C18—C23—H23C109.5
C9—N2—H2119.0H23A—C23—H23C109.5
C5—N2—H2119.0H23B—C23—H23C109.5
C10—N3—H3A109.5O6—C24—O5126.5 (5)
C10—N3—H3B109.5O6—C24—C19116.4 (4)
H3A—N3—H3B109.5O5—C24—C19117.1 (4)
C10—N3—H3C109.5O8—C25—N5123.8 (5)
H3A—N3—H3C109.5O8—C25—C26121.5 (4)
H3B—N3—H3C109.5N5—C25—C26114.5 (4)
C2—C1—S1116.5 (3)N6—C26—C27112.0 (4)
C2—C1—H1A108.2N6—C26—C25106.9 (4)
S1—C1—H1A108.2C27—C26—C25107.5 (4)
C2—C1—H1B108.2N6—C26—H26110.1
S1—C1—H1B108.2C27—C26—H26110.1
H1A—C1—H1B107.3C25—C26—H26110.1
C3—C2—C7123.0 (4)C28—C27—C32120.5 (5)
C3—C2—C1123.0 (4)C28—C27—C26118.6 (4)
C7—C2—C1113.9 (4)C32—C27—C26120.8 (5)
C2—C3—N1120.2 (4)C27—C28—C29119.9 (5)
C2—C3—C8127.1 (4)C27—C28—H28120.1
N1—C3—C8112.5 (4)C29—C28—H28120.1
N1—C4—C587.6 (3)C30—C29—C28119.5 (5)
N1—C4—S1109.6 (3)C30—C29—H29120.3
C5—C4—S1116.0 (3)C28—C29—H29120.3
N1—C4—H4113.6C29—C30—C31121.0 (5)
C5—C4—H4113.6C29—C30—H30119.5
S1—C4—H4113.6C31—C30—H30119.5
N2—C5—C4117.4 (4)C32—C31—C30119.3 (6)
N2—C5—C6116.1 (4)C32—C31—H31120.3
C4—C5—C685.5 (4)C30—C31—H31120.4
N2—C5—H5111.8C31—C32—C27119.9 (5)
C4—C5—H5111.8C31—C32—H32120.1
C6—C5—H5111.8C27—C32—H32120.1
O3—C6—N1132.8 (5)C36—S3—C10291.0 (5)
O3—C6—C5136.8 (5)C36—S3—C3396.2 (4)
N1—C6—C590.4 (4)C38—N7—C35130.8 (6)
C2—C7—H7A109.5C38—N7—C3694.3 (4)
C2—C7—H7B109.5C35—N7—C36127.0 (5)
H7A—C7—H7B109.5C41—N8—C37122.0 (4)
C2—C7—H7C109.5C41—N8—H8119.0
H7A—C7—H7C109.5C37—N8—H8119.0
H7B—C7—H7C109.5C42—N9—H9A109.5
O1—C8—O2125.6 (5)C42—N9—H9B109.5
O1—C8—C3116.1 (4)H9A—N9—H9B109.5
O2—C8—C3118.3 (4)C42—N9—H9C109.5
O4—C9—N2124.1 (5)H9A—N9—H9C109.5
O4—C9—C10120.8 (5)H9B—N9—H9C109.5
N2—C9—C10114.8 (4)C34—C33—S3118.0 (7)
N3—C10—C11112.8 (4)C34—C33—H33A107.8
N3—C10—C9107.6 (4)S3—C33—H33A107.8
C11—C10—C9107.6 (4)C34—C33—H33B107.8
N3—C10—H10109.6S3—C33—H33B107.8
C11—C10—H10109.6H33A—C33—H33B107.1
C9—C10—H10109.6C35—C34—C39129.8 (11)
C12—C11—C16118.7 (5)C35—C34—C33116.9 (11)
C12—C11—C10119.4 (5)C39—C34—C33110.2 (9)
C16—C11—C10121.8 (5)C34—C35—N7126.5 (8)
C11—C12—C13120.7 (6)C34—C35—C40116.2 (9)
C11—C12—H12119.6N7—C35—C40115.1 (5)
C13—C12—H12119.7N7—C36—C3787.3 (4)
C12—C13—C14119.5 (6)N7—C36—S3110.1 (4)
C12—C13—H13120.2C37—C36—S3115.8 (4)
C14—C13—H13120.2N7—C36—H36113.6
C15—C14—C13119.6 (5)C37—C36—H36113.6
C15—C14—H14120.2S3—C36—H36113.6
C13—C14—H14120.2N8—C37—C38116.2 (4)
C14—C15—C16120.8 (6)N8—C37—C36117.6 (4)
C14—C15—H15119.6C38—C37—C3685.7 (4)
C16—C15—H15119.6N8—C37—H37111.7
C15—C16—C11120.6 (5)C38—C37—H37111.7
C15—C16—H16119.7C36—C37—H37111.7
C11—C16—H16119.7O11—C38—N7132.4 (5)
C17—S2—C2193.6 (2)O11—C38—C37135.7 (5)
C22—N4—C19132.3 (4)N7—C38—C3791.9 (4)
C22—N4—C2194.1 (4)C34—C39—H39A109.5
C19—N4—C21127.1 (4)C34—C39—H39B109.5
C25—N5—C20120.4 (4)H39A—C39—H39B109.5
C25—N5—H5A119.8C34—C39—H39C109.5
C20—N5—H5A119.8H39A—C39—H39C109.5
C26—N6—H6A109.5H39B—C39—H39C109.5
C26—N6—H6B109.5O10—C40—O9126.3 (9)
H6A—N6—H6B109.5O10—C40—C35115.6 (9)
C26—N6—H6C109.5O9—C40—C35118.0 (7)
H6A—N6—H6C109.5O12—C41—N8124.5 (5)
H6B—N6—H6C109.5O12—C41—C42121.2 (5)
C18—C17—S2116.4 (3)N8—C41—C42113.8 (4)
C18—C17—H17A108.2N9—C42—C43111.2 (4)
S2—C17—H17A108.2N9—C42—C41108.4 (4)
C18—C17—H17B108.2C43—C42—C41108.0 (4)
S2—C17—H17B108.2N9—C42—H42109.7
H17A—C17—H17B107.3C43—C42—H42109.7
C19—C18—C17124.9 (5)C41—C42—H42109.7
C19—C18—C23121.9 (5)C48—C43—C44120.3 (5)
C17—C18—C23113.1 (4)C48—C43—C42119.7 (5)
C18—C19—N4118.2 (4)C44—C43—C42119.9 (5)
C18—C19—C24127.0 (4)C43—C44—C45118.9 (6)
N4—C19—C24114.8 (4)C43—C44—H44120.5
N5—C20—C22114.8 (4)C45—C44—H44120.5
N5—C20—C21119.1 (4)C46—C45—C44119.8 (6)
C22—C20—C2184.7 (3)C46—C45—H45120.1
N5—C20—H20111.9C44—C45—H45120.1
C22—C20—H20111.9C45—C46—C47121.8 (5)
C21—C20—H20111.9C45—C46—H46119.1
N4—C21—C2088.2 (3)C47—C46—H46119.1
N4—C21—S2110.3 (3)C46—C47—C48118.5 (6)
C20—C21—S2115.4 (3)C46—C47—H47120.8
N4—C21—H21113.5C48—C47—H47120.8
C20—C21—H21113.5C43—C48—C47120.5 (6)
S2—C21—H21113.5C43—C48—H48119.8
O7—C22—N4132.3 (5)C47—C48—H48119.8
O7—C22—C20135.3 (4)
C4—S1—C1—C249.0 (4)C18—C19—C24—O6136.2 (5)
S1—C1—C2—C324.6 (6)N4—C19—C24—O641.7 (6)
S1—C1—C2—C7158.5 (4)C18—C19—C24—O544.1 (7)
C7—C2—C3—N1175.3 (4)N4—C19—C24—O5138.1 (4)
C1—C2—C3—N11.3 (7)C20—N5—C25—O82.5 (7)
C7—C2—C3—C81.8 (7)C20—N5—C25—C26172.7 (4)
C1—C2—C3—C8174.8 (4)O8—C25—C26—N627.3 (6)
C6—N1—C3—C2140.3 (5)N5—C25—C26—N6157.4 (4)
C4—N1—C3—C211.4 (7)O8—C25—C26—C2793.1 (5)
C6—N1—C3—C845.3 (7)N5—C25—C26—C2782.2 (5)
C4—N1—C3—C8162.9 (4)N6—C26—C27—C28131.8 (5)
C6—N1—C4—C53.3 (4)C25—C26—C27—C28111.1 (5)
C3—N1—C4—C5163.2 (4)N6—C26—C27—C3251.9 (6)
C6—N1—C4—S1113.5 (3)C25—C26—C27—C3265.2 (6)
C3—N1—C4—S146.4 (5)C32—C27—C28—C291.8 (9)
C1—S1—C4—N156.3 (4)C26—C27—C28—C29174.5 (5)
C1—S1—C4—C5153.5 (4)C27—C28—C29—C302.6 (10)
C9—N2—C5—C4116.1 (5)C28—C29—C30—C312.5 (11)
C9—N2—C5—C6145.0 (4)C29—C30—C31—C321.7 (11)
N1—C4—C5—N2120.0 (4)C30—C31—C32—C270.9 (10)
S1—C4—C5—N29.4 (5)C28—C27—C32—C311.0 (9)
N1—C4—C5—C62.9 (3)C26—C27—C32—C31175.3 (6)
S1—C4—C5—C6107.8 (4)C36—S3—C33—C3447.6 (9)
C3—N1—C6—O318.3 (9)S3—C33—C34—C3535.3 (14)
C4—N1—C6—O3175.6 (5)S3—C33—C34—C39162.8 (9)
C3—N1—C6—C5160.6 (5)C39—C34—C35—N7175.3 (11)
C4—N1—C6—C53.3 (4)C33—C34—C35—N717.6 (17)
N2—C5—C6—O357.4 (8)C102—C34—C35—N731.1 (14)
C4—C5—C6—O3175.7 (6)C39—C34—C35—C101113 (2)
N2—C5—C6—N1121.5 (4)C33—C34—C35—C10144.8 (16)
C4—C5—C6—N13.1 (3)C39—C34—C35—C4022.1 (19)
C2—C3—C8—O1128.3 (5)C33—C34—C35—C40179.9 (9)
N1—C3—C8—O145.6 (6)C38—N7—C35—C34117.7 (12)
C2—C3—C8—O249.1 (7)C36—N7—C35—C3423.0 (14)
N1—C3—C8—O2137.0 (4)C38—N7—C35—C101141.6 (8)
C5—N2—C9—O410.4 (7)C36—N7—C35—C1011.0 (11)
C5—N2—C9—C10163.5 (4)C38—N7—C35—C4045.0 (9)
O4—C9—C10—N344.5 (6)C36—N7—C35—C40174.4 (7)
N2—C9—C10—N3141.5 (4)C38—N7—C36—C377.0 (4)
O4—C9—C10—C1177.3 (6)C35—N7—C36—C37158.2 (6)
N2—C9—C10—C1196.7 (5)C38—N7—C36—S3109.5 (4)
N3—C10—C11—C12132.8 (5)C35—N7—C36—S341.7 (8)
C9—C10—C11—C12108.7 (5)C102—S3—C36—N766.6 (7)
N3—C10—C11—C1649.6 (6)C33—S3—C36—N745.8 (6)
C9—C10—C11—C1668.9 (6)C102—S3—C36—C37163.6 (7)
C16—C11—C12—C130.4 (8)C33—S3—C36—C37142.8 (6)
C10—C11—C12—C13178.1 (5)C41—N8—C37—C38148.2 (4)
C11—C12—C13—C140.3 (9)C41—N8—C37—C36112.5 (6)
C12—C13—C14—C151.7 (9)N7—C36—C37—N8123.7 (5)
C13—C14—C15—C162.3 (9)S3—C36—C37—N812.7 (7)
C14—C15—C16—C111.6 (9)N7—C36—C37—C386.3 (4)
C12—C11—C16—C150.2 (8)S3—C36—C37—C38104.7 (5)
C10—C11—C16—C15177.4 (5)C35—N7—C38—O1123.9 (10)
C21—S2—C17—C1848.9 (4)C36—N7—C38—O11173.3 (6)
S2—C17—C18—C1924.7 (7)C35—N7—C38—C37156.6 (6)
S2—C17—C18—C23158.7 (4)C36—N7—C38—C377.1 (4)
C17—C18—C19—N42.9 (7)N8—C37—C38—O1155.0 (8)
C23—C18—C19—N4173.4 (4)C36—C37—C38—O11173.7 (6)
C17—C18—C19—C24179.3 (5)N8—C37—C38—N7125.5 (4)
C23—C18—C19—C244.4 (8)C36—C37—C38—N76.8 (4)
C22—N4—C19—C18135.7 (5)C34—C35—C40—O10147.0 (10)
C21—N4—C19—C188.3 (7)N7—C35—C40—O1048.5 (11)
C22—N4—C19—C2446.3 (7)C101—C35—C40—O10123.2 (11)
C21—N4—C19—C24169.8 (4)C34—C35—C40—O934.3 (13)
C25—N5—C20—C22159.5 (4)N7—C35—C40—O9130.2 (8)
C25—N5—C20—C21102.3 (5)C101—C35—C40—O958.0 (14)
C22—N4—C21—C206.0 (3)C37—N8—C41—O124.6 (7)
C19—N4—C21—C20160.1 (4)C37—N8—C41—C42167.7 (4)
C22—N4—C21—S2110.5 (3)O12—C41—C42—N938.2 (6)
C19—N4—C21—S243.7 (5)N8—C41—C42—N9149.3 (4)
N5—C20—C21—N4120.9 (4)O12—C41—C42—C4382.4 (6)
C22—C20—C21—N45.4 (3)N8—C41—C42—C4390.1 (5)
N5—C20—C21—S29.2 (5)N9—C42—C43—C4843.8 (7)
C22—C20—C21—S2106.3 (3)C41—C42—C43—C4875.1 (6)
C17—S2—C21—N454.9 (4)N9—C42—C43—C44137.6 (5)
C17—S2—C21—C20152.9 (4)C41—C42—C43—C44103.6 (6)
C19—N4—C22—O720.9 (9)C48—C43—C44—C450.3 (9)
C21—N4—C22—O7172.8 (5)C42—C43—C44—C45178.9 (5)
C19—N4—C22—C20158.0 (5)C43—C44—C45—C460.8 (10)
C21—N4—C22—C206.0 (3)C44—C45—C46—C472.7 (11)
N5—C20—C22—O753.4 (7)C45—C46—C47—C484.1 (11)
C21—C20—C22—O7173.1 (6)C44—C43—C48—C471.8 (10)
N5—C20—C22—N4125.5 (4)C42—C43—C48—C47179.6 (6)
C21—C20—C22—N45.8 (3)C46—C47—C48—C433.6 (11)
Symmetry codes: (i) x, y, z; (ii) x+1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O2iii0.882.223.077 (5)165
N3—H3A···O2iv0.911.892.780 (6)165
N3—H3B···O5v0.911.812.711 (5)173
N3—H3C···O150.911.912.811 (7)171
N5—H5A···O3iv0.882.032.883 (5)164
N6—H6A···O6v0.911.902.781 (6)161
N6—H6B···O150.912.182.874 (8)133
N6—H6B···O11vi0.912.392.995 (6)124
N6—H6B···O10vi0.912.393.134 (8)139
N6—H6C···O19vii0.911.992.794 (10)146
N6—H6C···O80.912.212.683 (6)112
N6—H6C···O19vi0.912.272.912 (10)128
N8—H8···O130.881.962.827 (6)167
N9—H9A···O17vi0.911.892.779 (8)166
N9—H9A···O17viii0.912.473.346 (8)162
N9—H9B···O10iv0.911.932.799 (7)160
N9—H9C···O7ix0.912.222.824 (5)124
N9—H9C···O4vi0.912.283.061 (6)144
Symmetry codes: (iii) x+1/2, y+1/2, z+1; (iv) x, y+1, z; (v) x, y1, z; (vi) x+1/2, y+1/2, z; (vii) x1/2, y+1/2, z; (viii) x+1/2, y+1/2, z; (ix) x+1/2, y1/2, z.

Experimental details

Crystal data
Chemical formulaC16H17N3O4S·1.9H2O
Mr381.88
Crystal system, space groupMonoclinic, C2
Temperature (K)150
a, b, c (Å)31.548 (2), 11.8574 (9), 15.6654 (11)
β (°) 112.364 (2)
V3)5419.3 (7)
Z12
Radiation typeSynchrotron, λ = 0.6891 Å
µ (mm1)0.22
Crystal size (mm)0.20 × 0.05 × 0.01
Data collection
DiffractometerBruker AXS SMART CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2001)
Tmin, Tmax0.96, 1.00
No. of measured, independent and
observed [I > 2σ(I)] reflections
14822, 10703, 8136
Rint0.047
(sin θ/λ)max1)0.636
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.074, 0.193, 1.01
No. of reflections10703
No. of parameters717
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.58, 0.47
Absolute structureFlack (1983)
Absolute structure parameter0.21 (10)

Computer programs: SMART (Bruker, 1995), SAINT (Bruker, 2000), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1974), SHELXL97.

Selected geometric parameters (Å, º) top
S1—C41.802 (5)C20—C211.544 (6)
S1—C11.807 (5)C25—C261.526 (7)
O1—C81.244 (6)C26—C271.524 (7)
O2—C81.268 (6)C27—C281.379 (8)
O3—C61.190 (6)C27—C321.387 (8)
O4—C91.221 (6)C28—C291.389 (8)
N1—C61.370 (7)C29—C301.377 (9)
N1—C31.415 (6)C30—C311.388 (10)
N1—C41.462 (6)C31—C321.384 (8)
N2—C91.333 (7)S3—C361.798 (6)
N2—C51.428 (6)S3—C1021.820 (15)
N3—C101.480 (7)S3—C331.892 (11)
C1—C21.519 (7)O9—C401.271 (12)
C2—C31.333 (6)O10—C401.207 (9)
C2—C71.478 (7)O11—C381.192 (7)
C3—C81.495 (7)O12—C411.208 (6)
C4—C51.549 (7)N7—C381.368 (8)
C5—C61.561 (7)N7—C351.407 (8)
C9—C101.545 (7)N7—C361.472 (8)
C10—C111.501 (7)N8—C411.339 (7)
C11—C121.378 (8)N8—C371.448 (7)
C11—C161.384 (7)N9—C421.487 (7)
C12—C131.384 (9)C33—C341.512 (17)
C13—C141.397 (10)C34—C351.294 (13)
C14—C151.354 (10)C34—C391.496 (17)
C15—C161.378 (8)C35—C1011.455 (14)
S2—C171.806 (6)C35—C401.530 (13)
S2—C211.809 (5)C36—C371.541 (8)
O5—C241.246 (6)C37—C381.523 (8)
O6—C241.246 (6)C41—C421.531 (7)
O7—C221.208 (6)C42—C431.527 (7)
O8—C251.219 (6)C43—C481.371 (8)
N4—C221.367 (6)C43—C441.381 (8)
N4—C191.403 (6)C44—C451.399 (9)
N4—C211.466 (6)C45—C461.350 (10)
N5—C251.354 (6)C46—C471.374 (10)
N5—C201.432 (6)C47—C481.388 (8)
N6—C261.482 (7)C100—C1011.51 (2)
C17—C181.502 (8)C101—C1021.54 (2)
C18—C191.340 (7)O14—O221.15 (3)
C18—C231.511 (8)O16—O211.67 (3)
C19—C241.523 (7)O18—O201.04 (2)
C20—C221.533 (7)
C4—S1—C194.1 (2)N4—C22—C2092.4 (4)
C6—N1—C3133.8 (4)O6—C24—O5126.5 (5)
C6—N1—C496.3 (4)O6—C24—C19116.4 (4)
C3—N1—C4125.8 (4)O5—C24—C19117.1 (4)
C9—N2—C5121.9 (4)O8—C25—N5123.8 (5)
C2—C1—S1116.5 (3)O8—C25—C26121.5 (4)
C3—C2—C7123.0 (4)N5—C25—C26114.5 (4)
C3—C2—C1123.0 (4)N6—C26—C27112.0 (4)
C7—C2—C1113.9 (4)N6—C26—C25106.9 (4)
C2—C3—N1120.2 (4)C27—C26—C25107.5 (4)
C2—C3—C8127.1 (4)C28—C27—C32120.5 (5)
N1—C3—C8112.5 (4)C28—C27—C26118.6 (4)
N1—C4—C587.6 (3)C32—C27—C26120.8 (5)
N1—C4—S1109.6 (3)C27—C28—C29119.9 (5)
C5—C4—S1116.0 (3)C30—C29—C28119.5 (5)
N2—C5—C4117.4 (4)C29—C30—C31121.0 (5)
N2—C5—C6116.1 (4)C32—C31—C30119.3 (6)
C4—C5—C685.5 (4)C31—C32—C27119.9 (5)
O3—C6—N1132.8 (5)C36—S3—C10291.0 (5)
O3—C6—C5136.8 (5)C36—S3—C3396.2 (4)
N1—C6—C590.4 (4)C38—N7—C35130.8 (6)
O1—C8—O2125.6 (5)C38—N7—C3694.3 (4)
O1—C8—C3116.1 (4)C35—N7—C36127.0 (5)
O2—C8—C3118.3 (4)C41—N8—C37122.0 (4)
O4—C9—N2124.1 (5)C34—C33—S3118.0 (7)
O4—C9—C10120.8 (5)C35—C34—C39129.8 (11)
N2—C9—C10114.8 (4)C35—C34—C33116.9 (11)
N3—C10—C11112.8 (4)C39—C34—C33110.2 (9)
N3—C10—C9107.6 (4)C34—C35—N7126.5 (8)
C11—C10—C9107.6 (4)C34—C35—C40116.2 (9)
C12—C11—C16118.7 (5)N7—C35—C40115.1 (5)
C12—C11—C10119.4 (5)N7—C36—C3787.3 (4)
C16—C11—C10121.8 (5)N7—C36—S3110.1 (4)
C11—C12—C13120.7 (6)C37—C36—S3115.8 (4)
C12—C13—C14119.5 (6)N8—C37—C38116.2 (4)
C15—C14—C13119.6 (5)N8—C37—C36117.6 (4)
C14—C15—C16120.8 (6)C38—C37—C3685.7 (4)
C15—C16—C11120.6 (5)O11—C38—N7132.4 (5)
C17—S2—C2193.6 (2)O11—C38—C37135.7 (5)
C22—N4—C19132.3 (4)N7—C38—C3791.9 (4)
C22—N4—C2194.1 (4)O10—C40—O9126.3 (9)
C19—N4—C21127.1 (4)O10—C40—C35115.6 (9)
C25—N5—C20120.4 (4)O9—C40—C35118.0 (7)
C18—C17—S2116.4 (3)O12—C41—N8124.5 (5)
C19—C18—C17124.9 (5)O12—C41—C42121.2 (5)
C19—C18—C23121.9 (5)N8—C41—C42113.8 (4)
C17—C18—C23113.1 (4)N9—C42—C43111.2 (4)
C18—C19—N4118.2 (4)N9—C42—C41108.4 (4)
C18—C19—C24127.0 (4)C43—C42—C41108.0 (4)
N4—C19—C24114.8 (4)C48—C43—C44120.3 (5)
N5—C20—C22114.8 (4)C48—C43—C42119.7 (5)
N5—C20—C21119.1 (4)C44—C43—C42119.9 (5)
C22—C20—C2184.7 (3)C43—C44—C45118.9 (6)
N4—C21—C2088.2 (3)C46—C45—C44119.8 (6)
N4—C21—S2110.3 (3)C45—C46—C47121.8 (5)
C20—C21—S2115.4 (3)C46—C47—C48118.5 (6)
O7—C22—N4132.3 (5)C43—C48—C47120.5 (6)
O7—C22—C20135.3 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O2i0.882.223.077 (5)164.9
N3—H3A···O2ii0.911.892.780 (6)165.2
N3—H3B···O5iii0.911.812.711 (5)172.8
N3—H3C···O150.911.912.811 (7)171.0
N5—H5A···O3ii0.882.032.883 (5)164.0
N6—H6A···O6iii0.911.902.781 (6)161.0
N6—H6B···O150.912.182.874 (8)133.0
N6—H6B···O11iv0.912.392.995 (6)124.2
N6—H6B···O10iv0.912.393.134 (8)138.8
N6—H6C···O19v0.911.992.794 (10)146.2
N6—H6C···O80.912.212.683 (6)111.9
N6—H6C···O19iv0.912.272.912 (10)127.5
N8—H8···O130.881.962.827 (6)166.7
N9—H9A···O17iv0.911.892.779 (8)165.6
N9—H9A···O17vi0.912.473.346 (8)162.3
N9—H9B···O10ii0.911.932.799 (7)160.0
N9—H9C···O7vii0.912.222.824 (5)123.5
N9—H9C···O4iv0.912.283.061 (6)144.1
Symmetry codes: (i) x+1/2, y+1/2, z+1; (ii) x, y+1, z; (iii) x, y1, z; (iv) x+1/2, y+1/2, z; (v) x1/2, y+1/2, z; (vi) x+1/2, y+1/2, z; (vii) x+1/2, y1/2, z.
 

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