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A new lamivudine hydrate, namely, cis-4-amino-1-(2-hydroxy­methyl-1,3-oxathio­lan-5-yl)pyrimidin-2(1H)-one hemi­hy­drate, C8H11N3O3S·0.5H2O, has been synthesized and structurally characterized by both powder and single-crystal X-ray diffraction studies. The hemihydrate crystallizes in the Sohnke space group P21, with the asymmetric unit comprising four lamivudine and two water mol­ecules. An extensive network of inter­molecular hydrogen bonds involving both lamivudine and solvent water mol­ecules generates a three-dimensional supra­molecular architecture. The structural data and crystal packing of the present lamivudine hemihydrate are compared with those of other hydrated and anhydrous forms of lamivudine.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270110020317/ln3144sup1.cif
Contains datablocks III, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270110020317/ln3144IIIsup2.hkl
Contains datablock III

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S0108270110020317/ln3144sup3.pdf
Supplementary material

CCDC reference: 786806

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: APEX2 (Bruker, 2007) and SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007) and XPREP (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: PLATON (Spek, 2009).

cis-4-amino-1-(2-hydroxymethyl-1,3-oxathiolan-5-yl)pyrimidin- 2(1H)-one hemihydrate top
Crystal data top
C8H11N3O3S·0.5H2OF(000) = 1000
Mr = 238.27Dx = 1.523 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 1512 reflections
a = 11.5729 (4) Åθ = 2.2–27.5°
b = 11.2385 (4) ŵ = 0.31 mm1
c = 16.0232 (6) ÅT = 120 K
β = 94.329 (1)°Plate, colourless
V = 2078.06 (13) Å30.35 × 0.25 × 0.08 mm
Z = 8
Data collection top
Bruker Kappa APEXII CCD area-detector
diffractometer
9309 independent reflections
Radiation source: fine-focus sealed tube8846 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
ω and φ scansθmax = 27.5°, θmin = 1.3°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
h = 1414
Tmin = 0.931, Tmax = 0.975k = 1414
28475 measured reflectionsl = 2020
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)] = 0.028H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.071 w = 1/[σ2(Fo2) + (0.0415P)2 + 0.2602P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
9309 reflectionsΔρmax = 0.43 e Å3
748 parametersΔρmin = 0.24 e Å3
3 restraintsAbsolute structure: Flack (1983), with 4338 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.00 (3)
Special details top

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*/Ueq
S1A0.10264 (4)0.99878 (4)0.51702 (3)0.02383 (10)
O1A0.18027 (10)0.83126 (11)0.30053 (7)0.0187 (2)
O2A0.03607 (10)0.81794 (12)0.53267 (7)0.0193 (2)
O3A0.19455 (12)0.76690 (12)0.60179 (8)0.0232 (3)
H3A0.232 (2)0.723 (3)0.6356 (17)0.044 (7)*
N1A0.02189 (12)0.79105 (12)0.38895 (9)0.0150 (3)
N2A0.04858 (12)0.70140 (13)0.25447 (9)0.0166 (3)
N3A0.09050 (14)0.57422 (14)0.21169 (10)0.0196 (3)
H3A10.055 (2)0.573 (2)0.1641 (16)0.030 (6)*
H3A20.154 (2)0.541 (2)0.2211 (13)0.020 (5)*
C1A0.08709 (14)0.77570 (15)0.31283 (10)0.0153 (3)
C2A0.05402 (14)0.64681 (15)0.26937 (10)0.0156 (3)
C3A0.12318 (15)0.66234 (16)0.34615 (11)0.0175 (3)
H3A30.1925 (19)0.6261 (19)0.3538 (13)0.018 (5)*
C4A0.08182 (14)0.73352 (15)0.40436 (10)0.0160 (3)
H4A0.1192 (16)0.7476 (17)0.4568 (12)0.011 (4)*
C5A0.07077 (15)0.86636 (16)0.45351 (10)0.0183 (3)
H5A0.1529 (19)0.857 (2)0.4432 (13)0.022*
C6A0.03015 (17)0.99557 (18)0.45002 (12)0.0242 (4)
H6A10.082 (2)1.046 (2)0.4704 (16)0.038 (7)*
H6A20.015 (2)1.023 (2)0.3959 (16)0.033 (6)*
C7A0.03189 (16)0.89922 (17)0.58589 (11)0.0200 (4)
H7A0.0200 (17)0.9431 (18)0.6172 (12)0.014 (5)*
C8A0.11294 (16)0.82985 (18)0.64642 (11)0.0212 (4)
H8A10.1476 (19)0.886 (2)0.6835 (14)0.024 (6)*
H8A20.061 (2)0.774 (2)0.6779 (15)0.031 (6)*
S1B0.38412 (4)0.72885 (4)0.78680 (3)0.02408 (10)
O1B0.19325 (11)0.67658 (11)1.02569 (8)0.0191 (3)
O2B0.33542 (10)0.51109 (11)0.83702 (8)0.0204 (3)
O3B0.29406 (12)0.53746 (13)0.65782 (8)0.0224 (3)
H3B0.257 (2)0.487 (2)0.6647 (15)0.030 (7)*
N1B0.18991 (12)0.53273 (13)0.92645 (9)0.0159 (3)
N2B0.04800 (13)0.54011 (13)1.02543 (9)0.0174 (3)
N3B0.09715 (14)0.40253 (15)1.02130 (10)0.0222 (3)
H3B10.1188 (19)0.437 (2)1.0633 (15)0.022 (6)*
H3B20.1313 (19)0.337 (2)1.0040 (14)0.026 (6)*
C1B0.14338 (15)0.58613 (15)0.99512 (10)0.0160 (3)
C2B0.00193 (15)0.44333 (15)0.99010 (10)0.0165 (3)
C3B0.04578 (15)0.38470 (16)0.92072 (11)0.0187 (3)
H3B30.0127 (17)0.3146 (19)0.8969 (12)0.015 (5)*
C4B0.13993 (16)0.43262 (16)0.89091 (11)0.0184 (3)
H4B0.1738 (18)0.3992 (19)0.8460 (14)0.019 (5)*
C5B0.29260 (15)0.59020 (15)0.89509 (10)0.0165 (3)
H5B0.3447 (17)0.6025 (18)0.9431 (13)0.015 (5)*
C6B0.26319 (18)0.70661 (18)0.84944 (13)0.0241 (4)
H6B10.256 (2)0.767 (3)0.8847 (17)0.042 (7)*
H6B20.192 (2)0.6965 (19)0.8143 (14)0.023 (5)*
C7B0.41645 (15)0.56786 (15)0.78702 (11)0.0176 (3)
H7B0.4936 (17)0.5593 (17)0.8109 (12)0.011 (5)*
C8B0.40431 (15)0.51356 (16)0.70081 (10)0.0171 (3)
H8B10.464 (2)0.545 (2)0.6667 (14)0.025 (5)*
H8B20.4155 (17)0.430 (2)0.7074 (12)0.016 (5)*
S1C0.92498 (4)0.64953 (5)0.79447 (3)0.02907 (11)
O1C0.67611 (11)0.60436 (11)1.03407 (8)0.0218 (3)
O2C0.71321 (10)0.61562 (11)0.83935 (8)0.0216 (3)
O3C0.65946 (13)0.42960 (14)0.71609 (9)0.0311 (3)
H3C0.682 (2)0.367 (3)0.7498 (19)0.057 (9)*
N1C0.68448 (13)0.75748 (13)0.94189 (9)0.0191 (3)
N2C0.55084 (13)0.75620 (13)1.04791 (9)0.0199 (3)
N3C0.41698 (14)0.90387 (15)1.05374 (11)0.0228 (3)
H3C10.3903 (19)0.860 (2)1.0912 (14)0.026 (6)*
H3C20.383 (2)0.968 (2)1.0325 (14)0.027 (6)*
C1C0.63674 (15)0.70238 (15)1.01073 (10)0.0183 (4)
C2C0.50664 (16)0.85927 (16)1.01747 (11)0.0191 (3)
C3C0.55421 (16)0.91914 (17)0.94919 (11)0.0205 (4)
H3C30.5253 (18)0.992 (2)0.9266 (13)0.020 (5)*
C4C0.64158 (16)0.86522 (16)0.91354 (11)0.0203 (4)
H4C0.681 (2)0.899 (2)0.8669 (14)0.027 (6)*
C5C0.77192 (15)0.69137 (16)0.90115 (11)0.0200 (4)
H5C0.8062 (18)0.640 (2)0.9427 (14)0.023 (5)*
C6C0.85694 (17)0.76322 (18)0.85408 (13)0.0251 (4)
H6C10.910 (2)0.798 (2)0.8893 (15)0.035 (6)*
H6C20.8204 (19)0.819 (2)0.8144 (14)0.028 (6)*
C7C0.79932 (15)0.54894 (17)0.80164 (12)0.0216 (4)
H7C0.8256 (17)0.484 (2)0.8361 (12)0.017 (5)*
C8C0.75462 (18)0.50669 (18)0.71542 (12)0.0263 (4)
H8C10.7348 (19)0.570 (2)0.6794 (13)0.021 (5)*
H8C20.8122 (16)0.4414 (16)0.6949 (12)0.018 (5)*
S1D0.58590 (4)0.82818 (4)0.46753 (3)0.02604 (11)
O1D0.69460 (10)0.95563 (11)0.73429 (7)0.0183 (3)
O2D0.49066 (10)0.73334 (11)0.59391 (7)0.0183 (2)
O3D0.32097 (12)0.59891 (12)0.48440 (9)0.0251 (3)
H3D0.317 (2)0.594 (3)0.539 (2)0.051 (8)*
N1D0.52631 (12)0.91979 (13)0.65703 (9)0.0151 (3)
N2D0.54373 (13)1.08002 (13)0.75296 (9)0.0170 (3)
N3D0.39039 (14)1.20452 (14)0.76809 (10)0.0197 (3)
H3D10.423 (2)1.223 (2)0.8170 (15)0.025 (6)*
H3D20.322 (2)1.229 (2)0.7506 (14)0.030 (6)*
C1D0.59221 (14)0.98640 (15)0.71644 (10)0.0159 (3)
C2D0.43511 (15)1.11399 (16)0.72838 (10)0.0171 (3)
C3D0.37021 (15)1.05367 (16)0.66130 (11)0.0180 (3)
H3D30.297 (2)1.077 (2)0.6427 (14)0.025 (6)*
C4D0.41738 (15)0.95566 (16)0.62999 (10)0.0175 (3)
H4D0.3789 (17)0.9051 (17)0.5924 (12)0.021 (5)*
C5D0.57911 (15)0.80682 (15)0.63029 (10)0.0164 (3)
H5D0.6174 (18)0.7733 (19)0.6790 (13)0.020*
C6D0.66983 (16)0.82753 (18)0.56750 (11)0.0210 (4)
H6D10.725 (2)0.763 (2)0.5697 (14)0.030 (6)*
H6D20.7126 (18)0.902 (2)0.5753 (13)0.020 (5)*
C7D0.50145 (16)0.70805 (17)0.50656 (11)0.0194 (3)
H7D0.5392 (18)0.631 (2)0.5046 (13)0.023*
C8D0.38183 (17)0.70200 (17)0.46208 (12)0.0228 (4)
H8D10.3382 (18)0.771 (2)0.4734 (13)0.021 (5)*
H8D20.3934 (19)0.695 (2)0.4010 (15)0.026 (6)*
O1W0.30651 (13)0.74973 (12)1.17322 (9)0.0232 (3)
H11W0.352 (2)0.698 (2)1.1904 (16)0.036 (7)*
H12W0.258 (2)0.725 (2)1.1381 (16)0.033 (6)*
O2W0.80960 (13)0.51185 (13)1.16824 (9)0.0234 (3)
H21W0.759 (3)0.541 (3)1.136 (2)0.056 (9)*
H22W0.846 (2)0.564 (2)1.1899 (16)0.033 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S1A0.0265 (2)0.0188 (2)0.0250 (2)0.00173 (18)0.00551 (17)0.00009 (18)
O1A0.0148 (6)0.0213 (6)0.0193 (6)0.0044 (5)0.0023 (4)0.0006 (5)
O2A0.0186 (6)0.0253 (6)0.0138 (5)0.0013 (5)0.0000 (4)0.0010 (5)
O3A0.0237 (7)0.0278 (7)0.0177 (6)0.0082 (5)0.0005 (5)0.0023 (5)
N1A0.0147 (7)0.0170 (7)0.0132 (6)0.0011 (5)0.0004 (5)0.0016 (5)
N2A0.0155 (7)0.0181 (7)0.0159 (7)0.0011 (5)0.0010 (5)0.0007 (5)
N3A0.0162 (8)0.0255 (8)0.0165 (7)0.0057 (6)0.0027 (6)0.0028 (6)
C1A0.0143 (8)0.0169 (8)0.0146 (8)0.0028 (6)0.0002 (6)0.0012 (6)
C2A0.0162 (8)0.0166 (8)0.0141 (8)0.0008 (6)0.0021 (6)0.0008 (6)
C3A0.0145 (8)0.0199 (8)0.0178 (8)0.0034 (7)0.0008 (6)0.0004 (7)
C4A0.0149 (8)0.0172 (8)0.0156 (8)0.0002 (6)0.0017 (6)0.0000 (6)
C5A0.0163 (8)0.0231 (9)0.0153 (8)0.0039 (7)0.0005 (6)0.0020 (6)
C6A0.0286 (10)0.0203 (9)0.0224 (9)0.0077 (8)0.0058 (7)0.0027 (8)
C7A0.0202 (9)0.0237 (9)0.0159 (8)0.0015 (7)0.0006 (7)0.0053 (7)
C8A0.0222 (9)0.0264 (10)0.0147 (8)0.0002 (7)0.0014 (7)0.0010 (7)
S1B0.0299 (2)0.0170 (2)0.0270 (2)0.00575 (18)0.01265 (18)0.00229 (18)
O1B0.0235 (6)0.0172 (6)0.0165 (6)0.0029 (5)0.0009 (5)0.0019 (5)
O2B0.0223 (6)0.0174 (6)0.0227 (6)0.0013 (5)0.0104 (5)0.0002 (5)
O3B0.0206 (7)0.0217 (7)0.0238 (7)0.0051 (6)0.0052 (5)0.0055 (5)
N1B0.0172 (7)0.0173 (7)0.0134 (6)0.0005 (5)0.0031 (5)0.0007 (5)
N2B0.0196 (7)0.0189 (7)0.0139 (7)0.0008 (6)0.0029 (5)0.0001 (6)
N3B0.0236 (8)0.0216 (8)0.0221 (8)0.0034 (6)0.0064 (6)0.0055 (7)
C1B0.0192 (8)0.0163 (8)0.0121 (7)0.0017 (6)0.0010 (6)0.0013 (6)
C2B0.0177 (8)0.0166 (8)0.0150 (8)0.0020 (6)0.0004 (6)0.0024 (6)
C3B0.0202 (9)0.0179 (9)0.0178 (8)0.0019 (7)0.0001 (7)0.0034 (7)
C4B0.0217 (9)0.0191 (9)0.0145 (8)0.0013 (7)0.0015 (7)0.0019 (6)
C5B0.0156 (8)0.0189 (8)0.0152 (8)0.0018 (6)0.0024 (6)0.0010 (6)
C6B0.0258 (10)0.0207 (9)0.0274 (10)0.0028 (7)0.0125 (8)0.0054 (8)
C7B0.0155 (8)0.0183 (9)0.0195 (8)0.0010 (6)0.0033 (6)0.0015 (6)
C8B0.0169 (8)0.0160 (9)0.0184 (8)0.0002 (6)0.0013 (6)0.0012 (6)
S1C0.0221 (2)0.0265 (2)0.0401 (3)0.00417 (19)0.01204 (19)0.0019 (2)
O1C0.0280 (7)0.0174 (6)0.0195 (6)0.0009 (5)0.0015 (5)0.0012 (5)
O2C0.0168 (6)0.0215 (7)0.0269 (7)0.0036 (5)0.0049 (5)0.0058 (5)
O3C0.0295 (8)0.0293 (8)0.0336 (8)0.0003 (6)0.0040 (6)0.0007 (6)
N1C0.0224 (8)0.0187 (8)0.0159 (7)0.0004 (6)0.0008 (6)0.0012 (6)
N2C0.0240 (8)0.0185 (7)0.0168 (7)0.0011 (6)0.0004 (6)0.0009 (6)
N3C0.0260 (8)0.0195 (8)0.0232 (8)0.0042 (7)0.0039 (7)0.0044 (7)
C1C0.0236 (9)0.0168 (8)0.0137 (8)0.0049 (7)0.0042 (6)0.0006 (6)
C2C0.0228 (9)0.0176 (8)0.0162 (8)0.0021 (7)0.0037 (6)0.0018 (6)
C3C0.0262 (10)0.0173 (9)0.0174 (8)0.0001 (7)0.0026 (7)0.0018 (7)
C4C0.0242 (9)0.0203 (9)0.0158 (8)0.0016 (7)0.0027 (7)0.0019 (7)
C5C0.0201 (9)0.0207 (9)0.0186 (9)0.0005 (7)0.0020 (7)0.0008 (7)
C6C0.0217 (9)0.0244 (10)0.0295 (10)0.0055 (8)0.0036 (8)0.0023 (8)
C7C0.0179 (9)0.0188 (8)0.0288 (9)0.0025 (7)0.0053 (7)0.0010 (7)
C8C0.0322 (10)0.0209 (9)0.0255 (9)0.0028 (8)0.0016 (8)0.0008 (8)
S1D0.0290 (2)0.0316 (3)0.0181 (2)0.0064 (2)0.00526 (17)0.00166 (18)
O1D0.0134 (6)0.0225 (6)0.0184 (6)0.0008 (5)0.0021 (5)0.0012 (5)
O2D0.0215 (6)0.0188 (6)0.0151 (6)0.0048 (5)0.0038 (4)0.0012 (5)
O3D0.0287 (7)0.0237 (7)0.0223 (7)0.0045 (6)0.0032 (5)0.0011 (5)
N1D0.0144 (7)0.0159 (7)0.0151 (6)0.0016 (5)0.0021 (5)0.0002 (5)
N2D0.0186 (7)0.0164 (7)0.0158 (7)0.0017 (5)0.0010 (5)0.0003 (5)
N3D0.0196 (8)0.0197 (8)0.0193 (8)0.0012 (6)0.0015 (6)0.0019 (6)
C1D0.0171 (8)0.0176 (8)0.0131 (7)0.0033 (6)0.0016 (6)0.0039 (6)
C2D0.0178 (8)0.0193 (8)0.0141 (8)0.0034 (6)0.0010 (6)0.0033 (6)
C3D0.0144 (8)0.0217 (9)0.0174 (8)0.0012 (7)0.0019 (6)0.0006 (7)
C4D0.0159 (8)0.0210 (8)0.0154 (8)0.0038 (6)0.0006 (6)0.0002 (6)
C5D0.0181 (8)0.0151 (8)0.0158 (8)0.0007 (6)0.0007 (6)0.0011 (6)
C6D0.0189 (9)0.0235 (9)0.0210 (9)0.0007 (8)0.0044 (7)0.0016 (7)
C7D0.0245 (9)0.0185 (9)0.0157 (8)0.0014 (7)0.0041 (6)0.0009 (6)
C8D0.0278 (10)0.0215 (9)0.0186 (9)0.0011 (7)0.0011 (7)0.0008 (7)
O1W0.0258 (7)0.0200 (7)0.0225 (7)0.0033 (6)0.0063 (6)0.0009 (5)
O2W0.0226 (7)0.0250 (7)0.0221 (6)0.0022 (6)0.0016 (5)0.0006 (6)
Geometric parameters (Å, º) top
S1A—C6A1.8073 (19)O2C—C5C1.437 (2)
S1A—C7A1.810 (2)O3C—C8C1.402 (3)
O1A—C1A1.249 (2)O3C—H3C0.91 (3)
O2A—C5A1.410 (2)N1C—C4C1.373 (2)
O2A—C7A1.442 (2)N1C—C1C1.413 (2)
O3A—C8A1.416 (2)N1C—C5C1.450 (2)
O3A—H3A0.83 (3)N2C—C1C1.341 (2)
N1A—C4A1.369 (2)N2C—C2C1.343 (2)
N1A—C1A1.396 (2)N3C—C2C1.325 (3)
N1A—C5A1.481 (2)N3C—H3C10.85 (2)
N2A—C2A1.342 (2)N3C—H3C20.87 (3)
N2A—C1A1.354 (2)C1C—O1C1.239 (2)
N3A—C2A1.325 (2)C2C—C3C1.430 (3)
N3A—H3A10.84 (2)C3C—C4C1.343 (3)
N3A—H3A20.82 (2)C3C—H3C30.95 (2)
C2A—C3A1.427 (2)C4C—H4C0.98 (2)
C3A—C4A1.344 (2)C5C—C6C1.517 (3)
C3A—H3A30.90 (2)C5C—H5C0.95 (2)
C4A—H4A0.929 (19)C6C—H6C10.89 (3)
C5A—C6A1.529 (3)C6C—H6C20.97 (2)
C5A—H5A0.96 (2)C7C—C8C1.514 (3)
C6A—H6A10.90 (3)C7C—H7C0.96 (2)
C6A—H6A20.95 (3)C8C—H8C10.94 (2)
C7A—C8A1.514 (2)C8C—H8C21.060 (15)
C7A—H7A0.95 (2)S1D—C7D1.8059 (19)
C8A—H8A10.94 (2)S1D—C6D1.8095 (19)
C8A—H8A21.02 (2)O1D—C1D1.247 (2)
S1B—C6B1.800 (2)O2D—C5D1.407 (2)
S1B—C7B1.8475 (18)O2D—C7D1.443 (2)
O1B—C1B1.250 (2)O3D—C8D1.416 (2)
O2B—C5B1.404 (2)O3D—H3D0.88 (3)
O2B—C7B1.429 (2)N1D—C4D1.363 (2)
O3B—C8B1.429 (2)N1D—C1D1.392 (2)
O3B—H3B0.73 (3)N1D—C5D1.486 (2)
N1B—C4B1.369 (2)N2D—C2D1.344 (2)
N1B—C1B1.397 (2)N2D—C1D1.347 (2)
N1B—C5B1.474 (2)N3D—C2D1.326 (2)
N2B—C2B1.337 (2)N3D—H3D10.87 (2)
N2B—C1B1.343 (2)N3D—H3D20.86 (2)
N3B—C2B1.326 (2)C1D—O1D1.247 (2)
N3B—H3B10.83 (2)C2D—C3D1.434 (2)
N3B—H3B20.87 (3)C3D—C4D1.343 (3)
C1B—O1B1.250 (2)C3D—H3D30.92 (2)
C2B—C3B1.438 (2)C4D—H4D0.918 (15)
C3B—C4B1.336 (3)C5D—O2D1.407 (2)
C3B—H3B30.94 (2)C5D—C6D1.526 (2)
C4B—H4B0.93 (2)C5D—H5D0.95 (2)
C5B—C6B1.525 (2)C6D—H6D10.96 (3)
C5B—H5B0.95 (2)C6D—H6D20.97 (2)
C6B—H6B10.89 (3)C7D—O2D1.443 (2)
C6B—H6B20.97 (2)C7D—C8D1.510 (3)
C7B—C8B1.507 (2)C7D—H7D0.97 (2)
C7B—H7B0.95 (2)C8D—O3D1.416 (2)
C8B—O3B1.429 (2)C8D—H8D10.95 (2)
C8B—H8B10.98 (2)C8D—H8D21.00 (2)
C8B—H8B20.95 (2)O1W—H11W0.82 (3)
S1C—C6C1.811 (2)O1W—H12W0.81 (3)
S1C—C7C1.8524 (19)O2W—H21W0.82 (3)
O1C—C1C1.239 (2)O2W—H22W0.79 (3)
O2C—C7C1.418 (2)
C6A—S1A—C7A86.93 (9)C1C—N1C—C5C117.01 (14)
C5A—O2A—C7A113.15 (14)C1C—N2C—C2C120.16 (16)
C8A—O3A—H3A108 (2)C2C—N3C—H3C1115.5 (16)
C4A—N1A—C1A120.52 (14)C2C—N3C—H3C2119.0 (15)
C4A—N1A—C5A121.30 (13)H3C1—N3C—H3C2125 (2)
C1A—N1A—C5A118.11 (13)O1C—C1C—N2C122.34 (17)
C2A—N2A—C1A119.48 (14)O1C—C1C—N2C122.34 (17)
C2A—N3A—H3A1119.0 (17)O1C—C1C—N1C117.95 (17)
C2A—N3A—H3A2118.2 (15)O1C—C1C—N1C117.95 (17)
H3A1—N3A—H3A2122 (2)N2C—C1C—N1C119.71 (15)
O1A—C1A—N2A121.65 (14)N3C—C2C—N2C117.15 (17)
O1A—C1A—N1A118.65 (15)N3C—C2C—C3C121.13 (17)
N2A—C1A—N1A119.70 (15)N2C—C2C—C3C121.72 (17)
N3A—C2A—N2A118.78 (15)C4C—C3C—C2C117.32 (17)
N3A—C2A—C3A119.27 (16)C4C—C3C—H3C3119.0 (13)
N2A—C2A—C3A121.92 (16)C2C—C3C—H3C3123.7 (13)
C4A—C3A—C2A117.72 (16)C3C—C4C—N1C121.49 (17)
C4A—C3A—H3A3122.3 (13)C3C—C4C—H4C123.9 (14)
C2A—C3A—H3A3119.9 (13)N1C—C4C—H4C114.6 (14)
C3A—C4A—N1A120.61 (15)O2C—C5C—N1C107.70 (13)
C3A—C4A—H4A124.3 (12)O2C—C5C—C6C105.27 (15)
N1A—C4A—H4A115.1 (12)N1C—C5C—C6C116.88 (15)
O2A—C5A—N1A108.05 (13)O2C—C5C—H5C105.9 (14)
O2A—C5A—C6A109.38 (14)N1C—C5C—H5C105.5 (14)
N1A—C5A—C6A112.49 (15)C6C—C5C—H5C115.0 (13)
O2A—C5A—H5A109.1 (13)C5C—C6C—S1C102.18 (13)
N1A—C5A—H5A104.2 (13)C5C—C6C—H6C1111.1 (16)
C6A—C5A—H5A113.4 (14)S1C—C6C—H6C1109.7 (16)
C5A—C6A—S1A104.31 (12)C5C—C6C—H6C2113.8 (14)
C5A—C6A—H6A1111.6 (17)S1C—C6C—H6C2107.2 (13)
S1A—C6A—H6A1109.3 (16)H6C1—C6C—H6C2112 (2)
C5A—C6A—H6A2114.6 (15)O2C—C7C—C8C110.59 (15)
S1A—C6A—H6A2109.3 (14)O2C—C7C—S1C106.51 (12)
H6A1—C6A—H6A2108 (2)C8C—C7C—S1C110.51 (14)
O2A—C7A—C8A109.68 (15)O2C—C7C—H7C111.4 (12)
O2A—C7A—S1A106.42 (11)C8C—C7C—H7C111.0 (12)
C8A—C7A—S1A114.97 (13)S1C—C7C—H7C106.7 (12)
O2A—C7A—H7A107.7 (12)O3C—C8C—C7C113.65 (16)
C8A—C7A—H7A108.3 (12)O3C—C8C—H8C1108.6 (13)
S1A—C7A—H7A109.5 (12)C7C—C8C—H8C1112.0 (13)
O3A—C8A—C7A109.77 (14)O3C—C8C—H8C295.0 (11)
O3A—C8A—H8A1112.8 (14)C7C—C8C—H8C2108.7 (11)
C7A—C8A—H8A1106.0 (13)H8C1—C8C—H8C2117.9 (17)
O3A—C8A—H8A2112.4 (14)C7D—S1D—C6D87.64 (9)
C7A—C8A—H8A2105.9 (13)C5D—O2D—C7D113.83 (13)
H8A1—C8A—H8A2109.6 (19)C8D—O3D—H3D111.5 (19)
C6B—S1B—C7B91.65 (9)C4D—N1D—C1D120.27 (15)
C5B—O2B—C7B111.61 (13)C4D—N1D—C5D123.48 (14)
C8B—O3B—H3B107 (2)C1D—N1D—C5D116.14 (13)
C4B—N1B—C1B120.32 (15)C2D—N2D—C1D120.38 (14)
C4B—N1B—C5B122.99 (14)C2D—N3D—H3D1117.3 (16)
C1B—N1B—C5B116.69 (14)C2D—N3D—H3D2118.1 (16)
C2B—N2B—C1B120.06 (15)H3D1—N3D—H3D2123 (2)
C2B—N3B—H3B1117.1 (16)O1D—C1D—N2D122.48 (15)
C2B—N3B—H3B2122.8 (15)O1D—C1D—N2D122.48 (15)
H3B1—N3B—H3B2120 (2)O1D—C1D—N1D118.02 (15)
O1B—C1B—N2B122.63 (16)O1D—C1D—N1D118.02 (15)
O1B—C1B—N2B122.63 (16)N2D—C1D—N1D119.50 (15)
O1B—C1B—N1B117.65 (15)N3D—C2D—N2D117.89 (15)
O1B—C1B—N1B117.65 (15)N3D—C2D—C3D121.40 (16)
N2B—C1B—N1B119.73 (15)N2D—C2D—C3D120.71 (16)
N3B—C2B—N2B117.81 (16)C4D—C3D—C2D117.57 (16)
N3B—C2B—C3B120.78 (16)C4D—C3D—H3D3120.3 (14)
N2B—C2B—C3B121.41 (16)C2D—C3D—H3D3122.0 (14)
C4B—C3B—C2B117.58 (16)C3D—C4D—N1D121.07 (15)
C4B—C3B—H3B3120.6 (12)C3D—C4D—H4D124.2 (14)
C2B—C3B—H3B3121.9 (12)N1D—C4D—H4D114.6 (13)
C3B—C4B—N1B120.86 (16)O2D—C5D—N1D108.59 (13)
C3B—C4B—H4B121.3 (13)O2D—C5D—N1D108.59 (13)
N1B—C4B—H4B117.8 (14)O2D—C5D—C6D109.37 (14)
O2B—C5B—N1B106.41 (13)O2D—C5D—C6D109.37 (14)
O2B—C5B—C6B107.61 (14)N1D—C5D—C6D112.22 (14)
N1B—C5B—C6B112.52 (14)O2D—C5D—H5D112.9 (13)
O2B—C5B—H5B113.2 (12)O2D—C5D—H5D112.9 (13)
N1B—C5B—H5B105.4 (12)N1D—C5D—H5D106.2 (13)
C6B—C5B—H5B111.6 (13)C6D—C5D—H5D107.6 (13)
C5B—C6B—S1B103.40 (13)C5D—C6D—S1D103.54 (12)
C5B—C6B—H6B1111.9 (17)C5D—C6D—H6D1110.4 (14)
S1B—C6B—H6B1111.3 (17)S1D—C6D—H6D1110.3 (14)
C5B—C6B—H6B2109.1 (13)C5D—C6D—H6D2114.5 (12)
S1B—C6B—H6B2110.8 (13)S1D—C6D—H6D2110.1 (12)
H6B1—C6B—H6B2110 (2)H6D1—C6D—H6D2107.9 (18)
O2B—C7B—C8B108.26 (14)O2D—C7D—C8D108.87 (15)
O2B—C7B—S1B107.27 (11)O2D—C7D—C8D108.87 (15)
C8B—C7B—S1B112.95 (12)O2D—C7D—S1D106.10 (12)
O2B—C7B—H7B111.5 (12)O2D—C7D—S1D106.10 (12)
C8B—C7B—H7B110.4 (12)C8D—C7D—S1D111.78 (13)
S1B—C7B—H7B106.5 (12)O2D—C7D—H7D106.2 (13)
O3B—C8B—C7B112.57 (14)O2D—C7D—H7D106.2 (13)
O3B—C8B—C7B112.57 (14)C8D—C7D—H7D110.1 (12)
O3B—C8B—H8B1107.8 (13)S1D—C7D—H7D113.5 (13)
O3B—C8B—H8B1107.8 (13)O3D—C8D—C7D111.93 (15)
C7B—C8B—H8B1110.0 (13)O3D—C8D—C7D111.93 (15)
O3B—C8B—H8B2110.4 (12)O3D—C8D—H8D1109.9 (13)
O3B—C8B—H8B2110.4 (12)O3D—C8D—H8D1109.9 (13)
C7B—C8B—H8B2107.1 (12)C7D—C8D—H8D1110.7 (13)
H8B1—C8B—H8B2108.8 (19)O3D—C8D—H8D2106.5 (13)
C6C—S1C—C7C91.33 (9)O3D—C8D—H8D2106.5 (13)
C7C—O2C—C5C107.20 (13)C7D—C8D—H8D2106.3 (13)
C8C—O3C—H3C107.1 (19)H8D1—C8D—H8D2111.4 (18)
C4C—N1C—C1C119.45 (15)H11W—O1W—H12W112 (3)
C4C—N1C—C5C123.39 (15)H21W—O2W—H22W108 (3)
C2A—N2A—C1A—O1A177.71 (16)C4C—N1C—C1C—N2C0.5 (2)
C2A—N2A—C1A—N1A2.5 (2)C5C—N1C—C1C—N2C176.19 (15)
C4A—N1A—C1A—O1A178.79 (15)C1C—N2C—C2C—N3C175.73 (16)
C5A—N1A—C1A—O1A4.1 (2)C1C—N2C—C2C—C3C4.6 (3)
C4A—N1A—C1A—N2A1.4 (2)N3C—C2C—C3C—C4C177.03 (17)
C5A—N1A—C1A—N2A175.76 (15)N2C—C2C—C3C—C4C3.3 (3)
C1A—N2A—C2A—N3A179.93 (16)C2C—C3C—C4C—N1C0.6 (3)
C1A—N2A—C2A—C3A1.6 (3)C1C—N1C—C4C—C3C0.7 (3)
N3A—C2A—C3A—C4A177.86 (17)C5C—N1C—C4C—C3C174.69 (16)
N2A—C2A—C3A—C4A0.5 (3)C7C—O2C—C5C—N1C178.33 (14)
C2A—C3A—C4A—N1A1.6 (3)C7C—O2C—C5C—C6C56.28 (17)
C1A—N1A—C4A—C3A0.7 (3)C4C—N1C—C5C—O2C89.05 (19)
C5A—N1A—C4A—C3A177.77 (16)C1C—N1C—C5C—O2C86.47 (17)
C7A—O2A—C5A—N1A119.70 (15)C4C—N1C—C5C—C6C29.1 (2)
C7A—O2A—C5A—C6A3.05 (19)C1C—N1C—C5C—C6C155.38 (16)
C4A—N1A—C5A—O2A31.7 (2)O2C—C5C—C6C—S1C47.65 (15)
C1A—N1A—C5A—O2A145.45 (14)N1C—C5C—C6C—S1C167.11 (12)
C4A—N1A—C5A—C6A89.18 (19)C7C—S1C—C6C—C5C22.58 (13)
C1A—N1A—C5A—C6A93.70 (17)C5C—O2C—C7C—C8C156.71 (15)
O2A—C5A—C6A—S1A31.40 (17)C5C—O2C—C7C—S1C36.59 (16)
N1A—C5A—C6A—S1A88.67 (15)C6C—S1C—C7C—O2C6.72 (13)
C7A—S1A—C6A—C5A39.11 (13)C6C—S1C—C7C—C8C126.89 (15)
C5A—O2A—C7A—C8A151.83 (14)O2C—C7C—C8C—O3C62.5 (2)
C5A—O2A—C7A—S1A26.89 (16)S1C—C7C—C8C—O3C179.77 (13)
C6A—S1A—C7A—O2A38.45 (12)O1D—O1D—C1D—N2D0.00 (19)
C6A—S1A—C7A—C8A160.07 (14)O1D—O1D—C1D—N1D0.00 (17)
O2A—C7A—C8A—O3A65.01 (19)C2D—N2D—C1D—O1D176.25 (16)
S1A—C7A—C8A—O3A54.83 (19)C2D—N2D—C1D—O1D176.25 (16)
O1B—O1B—C1B—N2B0.0 (2)C2D—N2D—C1D—N1D4.4 (2)
O1B—O1B—C1B—N1B0.0 (3)C4D—N1D—C1D—O1D174.27 (15)
C2B—N2B—C1B—O1B179.83 (15)C5D—N1D—C1D—O1D9.3 (2)
C2B—N2B—C1B—O1B179.83 (15)C4D—N1D—C1D—O1D174.27 (15)
C2B—N2B—C1B—N1B0.2 (2)C5D—N1D—C1D—O1D9.3 (2)
C4B—N1B—C1B—O1B179.21 (15)C4D—N1D—C1D—N2D6.4 (2)
C5B—N1B—C1B—O1B1.4 (2)C5D—N1D—C1D—N2D170.07 (14)
C4B—N1B—C1B—O1B179.21 (15)C1D—N2D—C2D—N3D178.06 (15)
C5B—N1B—C1B—O1B1.4 (2)C1D—N2D—C2D—C3D1.9 (2)
C4B—N1B—C1B—N2B1.2 (2)N3D—C2D—C3D—C4D173.54 (17)
C5B—N1B—C1B—N2B178.25 (14)N2D—C2D—C3D—C4D6.4 (3)
C1B—N2B—C2B—N3B178.79 (16)C2D—C3D—C4D—N1D4.5 (3)
C1B—N2B—C2B—C3B1.4 (2)C1D—N1D—C4D—C3D1.7 (2)
N3B—C2B—C3B—C4B178.10 (16)C5D—N1D—C4D—C3D174.48 (16)
N2B—C2B—C3B—C4B2.1 (3)C7D—O2D—C5D—O2D0 (10)
C2B—C3B—C4B—N1B1.2 (3)O2D—O2D—C5D—N1D0.00 (11)
C1B—N1B—C4B—C3B0.4 (2)C7D—O2D—C5D—N1D116.50 (15)
C5B—N1B—C4B—C3B178.96 (16)O2D—O2D—C5D—C6D0.00 (13)
C7B—O2B—C5B—N1B165.39 (13)C7D—O2D—C5D—C6D6.26 (19)
C7B—O2B—C5B—C6B44.57 (18)C4D—N1D—C5D—O2D15.8 (2)
C4B—N1B—C5B—O2B10.7 (2)C1D—N1D—C5D—O2D160.53 (13)
C1B—N1B—C5B—O2B169.88 (13)C4D—N1D—C5D—O2D15.8 (2)
C4B—N1B—C5B—C6B106.88 (19)C1D—N1D—C5D—O2D160.53 (13)
C1B—N1B—C5B—C6B72.51 (19)C4D—N1D—C5D—C6D105.22 (18)
O2B—C5B—C6B—S1B42.84 (16)C1D—N1D—C5D—C6D78.45 (17)
N1B—C5B—C6B—S1B159.74 (12)O2D—C5D—C6D—S1D33.23 (16)
C7B—S1B—C6B—C5B24.37 (14)O2D—C5D—C6D—S1D33.23 (16)
C5B—O2B—C7B—C8B146.39 (14)N1D—C5D—C6D—S1D87.35 (15)
C5B—O2B—C7B—S1B24.21 (16)C7D—S1D—C6D—C5D39.45 (13)
C6B—S1B—C7B—O2B2.00 (13)C5D—O2D—C7D—O2D0 (5)
C6B—S1B—C7B—C8B117.22 (14)O2D—O2D—C7D—C8D0.0 (4)
O3B—O3B—C8B—C7B0.0 (2)C5D—O2D—C7D—C8D144.39 (15)
O2B—C7B—C8B—O3B65.33 (18)O2D—O2D—C7D—S1D0.0 (4)
S1B—C7B—C8B—O3B53.31 (18)C5D—O2D—C7D—S1D23.95 (17)
O2B—C7B—C8B—O3B65.33 (18)C6D—S1D—C7D—O2D37.02 (13)
S1B—C7B—C8B—O3B53.31 (18)C6D—S1D—C7D—O2D37.02 (13)
O1C—O1C—C1C—N2C0.0 (3)C6D—S1D—C7D—C8D155.56 (14)
O1C—O1C—C1C—N1C0.0 (3)O3D—O3D—C8D—C7D0.00 (13)
C2C—N2C—C1C—O1C176.28 (15)O2D—C7D—C8D—O3D71.00 (19)
C2C—N2C—C1C—O1C176.28 (15)O2D—C7D—C8D—O3D71.00 (19)
C2C—N2C—C1C—N1C3.1 (2)S1D—C7D—C8D—O3D172.11 (13)
C4C—N1C—C1C—O1C178.95 (15)O2D—C7D—C8D—O3D71.00 (19)
C5C—N1C—C1C—O1C3.2 (2)O2D—C7D—C8D—O3D71.00 (19)
C4C—N1C—C1C—O1C178.95 (15)S1D—C7D—C8D—O3D172.11 (13)
C5C—N1C—C1C—O1C3.2 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3A—H3A···O3B0.83 (3)2.22 (3)2.9368 (19)144 (3)
N3A—H3A1···N2Bi0.84 (2)2.25 (3)3.012 (2)151 (2)
N3B—H3B2···O1Bii0.87 (3)1.98 (3)2.851 (2)173 (2)
O3B—H3B···O1Aiii0.73 (3)2.05 (3)2.7717 (19)168 (3)
N3C—H3C2···O1Civ0.87 (3)1.96 (3)2.826 (2)169 (2)
C6D—H6D2···O3Dv0.97 (2)2.43 (2)3.165 (2)131.8 (16)
C4C—H4C···O1D0.98 (2)2.24 (2)3.150 (2)155.2 (19)
N3D—H3D1···N2Civ0.87 (2)2.20 (2)3.031 (2)162 (2)
C6C—H6C2···O1D0.97 (2)2.42 (2)3.368 (2)167.6 (18)
C4B—H4B···O1Aiii0.93 (2)2.48 (2)3.338 (2)155.3 (17)
O3D—H3D···O3B0.88 (3)2.04 (3)2.903 (2)165 (3)
C8B—H8B1···O2D0.98 (2)2.44 (2)3.208 (2)134.3 (17)
N3A—H3A2···O1Dvi0.82 (2)2.08 (2)2.896 (2)170 (2)
N3D—H3D2···O1Avii0.86 (2)2.12 (3)2.958 (2)164 (2)
C3A—H3A3···O3D0.90 (2)2.49 (2)3.145 (2)129.7 (17)
O1W—H12W···O1B0.81 (3)1.98 (3)2.7411 (18)157 (3)
O1W—H11W···N2Dviii0.82 (3)1.97 (3)2.781 (2)172 (3)
O2W—H21W···O1C0.82 (3)1.96 (3)2.7546 (19)161 (3)
O2W—H22W···N2Aix0.79 (3)2.18 (3)2.966 (2)177 (3)
N3C—H3C1···O1W0.85 (2)2.10 (3)2.944 (2)173 (2)
O3C—H3C···O1Wviii0.91 (3)1.80 (3)2.698 (2)166 (3)
N3B—H3B1···O2Wx0.83 (2)2.11 (2)2.933 (2)174 (2)
Symmetry codes: (i) x, y, z1; (ii) x, y1/2, z+2; (iii) x, y1/2, z+1; (iv) x+1, y+1/2, z+2; (v) x+1, y+1/2, z+1; (vi) x+1, y1/2, z+1; (vii) x, y+1/2, z+1; (viii) x+1, y1/2, z+2; (ix) x+1, y, z+1; (x) x1, y, z.
Selected torsion angles (°) in lamivudine forms (I)–(III) top
CompoundMoleculeC1-N1-C5-O2C1-N1-C5-C6C4-N1-C5-O2C4-N1-C5-C6
(III)A145.45 (14)-93.70 (17)-31.7 (2)89.18 (19)
B169.88 (13)-72.51 (19)-10.7 (2)106.88 (19)
C86.47 (17)-155.38 (16)-89.05 (19)29.1 (2)
D160.53 (13)-78.45 (17)-15.8 (2)105.22 (18)
(I)A151.9 (5)-87.2 (6)-31.7 (7)89.2 (7)
B158.3 (5)-82.6 (6)-21.6 (7)97.5 (6)
C109.3 (6)-130.2 (6)-72.1 (7)48.4 (8)
D140.6 (5)-88.9 (12)-43.0 (7)87.5 (12)
D'140.6 (5)-107.8 (9)-43.0 (7)68.6 (9)
E143.8 (5)-75.4 (9)-32.0 (8)108.8 (8)
E'143.8 (5)-113.6 (7)-32.0 (8)70.6 (8)
(II)152.1 (4)-84.8 (5)-29.8 (6)93.3 (5)
 

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