# Electronic Supplementary Material (ESI) for CrystEngComm
# This journal is © The Royal Society of Chemistry 2012


data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'Dr Felipe Terra Martins'
_publ_contact_author_email       felipetmartins@yahoo.com.br

_publ_section_title              
;
Toward supramolecular architectures of
the anti-HIV drug lamivudine: understanding the effect
of the inclusion of water in a hydrochloride form

;

_publ_contact_author             'Martins, Felipe Terra'
loop_
_publ_author_name
F.Martins
N.Paparidis
J.Ellena

# Attachment '- CCDC_751365_to_751368.cif'

data_LamHCl_RT
_database_code_depnum_ccdc_archive 'CCDC 751365'
#TrackingRef '- CCDC_751365_to_751368.cif'

_audit_creation_date             2008-07-31T17:12:02-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#------------------ CHEMICAL INFORMATION ------------------------------------#

_chemical_formula_weight         265.72
_chemical_absolute_configuration '2R 5S'
_chemical_name_systematic        
;
4-amino-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]
-(1H)-pyrimidin-2-one hydrochloride
;

_chemical_name_common            
;
4-amino-1-((2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl) -
(1H)-pyrimidin-2-one hydrochloride
;
_chemical_formula_moiety         'C8 H12 N3 O3 S, Cl'
_chemical_formula_sum            'C8 H12 Cl N3 O3 S'
_chemical_compound_source        'Polymorph Screening'

#------------------ UNIT CELL INFORMATION -----------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.7060(2)
_cell_length_b                   11.9670(5)
_cell_length_c                   8.3401(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.273(2)
_cell_angle_gamma                90.00
_cell_volume                     551.91(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    4201
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      26.733

#------------------ CRYSTAL INFORMATION -------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.432
_exptl_crystal_size_mid          0.098
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    1.599
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             276
_exptl_absorpt_coefficient_mu    0.531
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
P. Coppens, L. Leiserowitz, D Rabinovich, Acta Cryst.
(1965), 18, 1035-1038
;
_exptl_absorpt_correction_T_min  0.866
_exptl_absorpt_correction_T_max  0.974

#------------------ DATA COLLECTION INFORMATION -----------------------------#

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_reflns_number            6374
_diffrn_reflns_av_R_equivalents  0.0646
_diffrn_reflns_av_sigmaI/netI    0.0552
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.04
_diffrn_reflns_theta_max         26.63
_diffrn_reflns_theta_full        26.63
_diffrn_measured_fraction_theta_max 0.99
_diffrn_measured_fraction_theta_full 0.99
_reflns_number_total             2284
_reflns_number_gt                2064
_reflns_threshold_expression     >2sigma(I)

#------------------ COMPUTER PROGRAMS USED ----------------------------------#

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

#------------------ REFINEMENT INFORMATION ----------------------------------#

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0497P)^2^+0.0870P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.09(7)
_refine_ls_number_reflns         2284
_refine_ls_number_parameters     157
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0365
_refine_ls_wR_factor_ref         0.0943
_refine_ls_wR_factor_gt          0.0896
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.051

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S3' S 0.55638(12) 0.01587(7) 0.36247(8) 0.0488(2) Uani 1 1 d . . .
Cl1 Cl 0.02131(13) 0.18155(6) 0.12771(9) 0.0483(2) Uani 1 1 d . . .
C4 C 0.3188(4) -0.0361(2) 0.9365(3) 0.0318(5) Uani 1 1 d . . .
O2 O 0.4820(4) 0.22765(16) 0.8132(3) 0.0415(4) Uani 1 1 d . . .
N3 N 0.3478(4) 0.07580(19) 0.9261(3) 0.0324(5) Uani 1 1 d . . .
O1' O 0.9234(3) 0.03692(16) 0.6186(2) 0.0374(4) Uani 1 1 d . . .
C2 C 0.4816(5) 0.1263(2) 0.8315(3) 0.0313(5) Uani 1 1 d . . .
N1 N 0.6105(4) 0.05617(17) 0.7551(3) 0.0328(5) Uani 1 1 d . . .
C5 C 0.4570(5) -0.1057(2) 0.8582(3) 0.0366(6) Uani 1 1 d . . .
H5 H 0.4495 -0.1831 0.8662 0.044 Uiso 1 1 calc R . .
N4 N 0.1671(4) -0.0740(2) 1.0180(3) 0.0397(5) Uani 1 1 d . . .
O5' O 0.9404(5) -0.1496(2) 0.2756(3) 0.0590(6) Uani 1 1 d . . .
C4' C 0.8764(5) 0.0011(2) 0.4480(3) 0.0369(5) Uani 1 1 d . . .
H4' H 0.9622 0.0507 0.3884 0.044 Uiso 1 1 calc R . .
C6 C 0.5993(5) -0.0573(2) 0.7721(3) 0.0345(5) Uani 1 1 d . . .
H6 H 0.6937 -0.1024 0.7223 0.041 Uiso 1 1 calc R . .
C2' C 0.5781(6) 0.1417(3) 0.4813(4) 0.0472(7) Uani 1 1 d . . .
H2'x H 0.6446 0.2021 0.4287 0.057 Uiso 1 1 calc R . .
H2'y H 0.4209 0.1640 0.4952 0.057 Uiso 1 1 calc R . .
C1' C 0.7468(5) 0.1111(2) 0.6457(3) 0.0353(5) Uani 1 1 d . . .
H1' H 0.8252 0.1788 0.6996 0.042 Uiso 1 1 calc R . .
C5' C 0.9693(6) -0.1166(2) 0.4419(4) 0.0472(7) Uani 1 1 d . . .
H5'y H 1.1389 -0.1199 0.4998 0.057 Uiso 1 1 calc R . .
H5'x H 0.8807 -0.1671 0.4964 0.057 Uiso 1 1 calc R . .
H4Nx H 0.092(6) -0.026(3) 1.064(4) 0.048 Uiso 1 1 d . . .
H3 H 0.257(6) 0.119(3) 0.970(5) 0.039 Uiso 1 1 d . . .
H5'O H 0.773(10) -0.176(4) 0.220(7) 0.089 Uiso 1 1 d . . .
H4Ny H 0.133(9) -0.153(4) 1.019(7) 0.048 Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S3' 0.0418(3) 0.0689(5) 0.0321(3) -0.0058(3) 0.0020(2) -0.0006(4)
Cl1 0.0577(4) 0.0410(3) 0.0518(4) 0.0068(3) 0.0240(3) 0.0134(3)
C4 0.0344(12) 0.0310(13) 0.0282(12) 0.0006(9) 0.0043(10) -0.0011(9)
O2 0.0496(11) 0.0284(10) 0.0481(11) -0.0004(8) 0.0151(8) 0.0025(8)
N3 0.0382(11) 0.0307(11) 0.0290(10) -0.0037(8) 0.0097(9) 0.0020(9)
O1' 0.0343(9) 0.0464(12) 0.0309(9) -0.0059(8) 0.0068(7) -0.0009(8)
C2 0.0366(12) 0.0257(14) 0.0303(12) -0.0015(10) 0.0056(9) 0.0004(9)
N1 0.0406(11) 0.0283(10) 0.0305(10) 0.0002(8) 0.0108(8) -0.0015(8)
C5 0.0482(15) 0.0270(12) 0.0356(15) 0.0014(10) 0.0126(11) 0.0013(10)
N4 0.0483(13) 0.0359(12) 0.0386(12) -0.0005(10) 0.0177(10) -0.0052(10)
O5' 0.0629(14) 0.0628(14) 0.0587(15) -0.0222(12) 0.0292(12) -0.0106(12)
C4' 0.0417(12) 0.0430(15) 0.0275(12) -0.0033(11) 0.0115(9) -0.0050(12)
C6 0.0416(13) 0.0268(12) 0.0354(13) -0.0017(10) 0.0102(10) 0.0033(10)
C2' 0.0537(16) 0.0481(16) 0.0393(15) 0.0093(12) 0.0109(12) 0.0057(13)
C1' 0.0402(13) 0.0328(13) 0.0352(13) 0.0002(10) 0.0135(10) -0.0030(10)
C5' 0.0542(16) 0.0465(17) 0.0452(16) -0.0056(12) 0.0202(13) -0.0016(13)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S3' C2' 1.790(3) . ?
S3' C4' 1.798(3) . ?
C4 N4 1.307(4) . ?
C4 N3 1.355(3) . ?
C4 C5 1.413(4) . ?
O2 C2 1.222(3) . ?
N3 C2 1.367(4) . ?
N3 H3 0.87(4) . ?
O1' C1' 1.402(3) . ?
O1' C4' 1.446(3) . ?
C2 N1 1.372(3) . ?
N1 C6 1.369(3) . ?
N1 C1' 1.490(3) . ?
C5 C6 1.341(4) . ?
C5 H5 0.9300 . ?
N4 H4Nx 0.86(4) . ?
N4 H4Ny 0.97(5) . ?
O5' C5' 1.413(4) . ?
O5' H5'O 1.01(6) . ?
C4' C5' 1.510(4) . ?
C4' H4' 0.9800 . ?
C6 H6 0.9300 . ?
C2' C1' 1.513(4) . ?
C2' H2'x 0.9700 . ?
C2' H2'y 0.9700 . ?
C1' H1' 0.9800 . ?
C5' H5'y 0.9700 . ?
C5' H5'x 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2' S3' C4' 86.44(13) . . ?
N4 C4 N3 118.9(2) . . ?
N4 C4 C5 123.6(2) . . ?
N3 C4 C5 117.5(2) . . ?
C4 N3 C2 124.6(2) . . ?
C4 N3 H3 117(2) . . ?
C2 N3 H3 117(2) . . ?
C1' O1' C4' 112.32(18) . . ?
O2 C2 N3 122.0(3) . . ?
O2 C2 N1 122.1(3) . . ?
N3 C2 N1 115.9(2) . . ?
C6 N1 C2 121.0(2) . . ?
C6 N1 C1' 123.1(2) . . ?
C2 N1 C1' 115.8(2) . . ?
C6 C5 C4 118.3(2) . . ?
C6 C5 H5 120.9 . . ?
C4 C5 H5 120.9 . . ?
C4 N4 H4Nx 118(2) . . ?
C4 N4 H4Ny 120(3) . . ?
H4Nx N4 H4Ny 122(4) . . ?
C5' O5' H5'O 114(3) . . ?
O1' C4' C5' 109.2(2) . . ?
O1' C4' S3' 106.57(16) . . ?
C5' C4' S3' 114.1(2) . . ?
O1' C4' H4' 108.9 . . ?
C5' C4' H4' 108.9 . . ?
S3' C4' H4' 108.9 . . ?
C5 C6 N1 122.3(2) . . ?
C5 C6 H6 118.9 . . ?
N1 C6 H6 118.9 . . ?
C1' C2' S3' 103.9(2) . . ?
C1' C2' H2'x 111.0 . . ?
S3' C2' H2'x 111.0 . . ?
C1' C2' H2'y 111.0 . . ?
S3' C2' H2'y 111.0 . . ?
H2'x C2' H2'y 109.0 . . ?
O1' C1' N1 108.9(2) . . ?
O1' C1' C2' 109.2(2) . . ?
N1 C1' C2' 110.5(2) . . ?
O1' C1' H1' 109.4 . . ?
N1 C1' H1' 109.4 . . ?
C2' C1' H1' 109.4 . . ?
O5' C5' C4' 109.7(3) . . ?
O5' C5' H5'y 109.7 . . ?
C4' C5' H5'y 109.7 . . ?
O5' C5' H5'x 109.7 . . ?
C4' C5' H5'x 109.7 . . ?
H5'y C5' H5'x 108.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N4 C4 N3 C2 -173.2(2) . . . . ?
C5 C4 N3 C2 7.1(4) . . . . ?
C4 N3 C2 O2 172.4(3) . . . . ?
C4 N3 C2 N1 -6.1(4) . . . . ?
O2 C2 N1 C6 -177.3(3) . . . . ?
N3 C2 N1 C6 1.2(4) . . . . ?
O2 C2 N1 C1' -1.3(4) . . . . ?
N3 C2 N1 C1' 177.2(2) . . . . ?
N4 C4 C5 C6 177.2(3) . . . . ?
N3 C4 C5 C6 -3.1(4) . . . . ?
C1' O1' C4' C5' -148.3(2) . . . . ?
C1' O1' C4' S3' -24.5(2) . . . . ?
C2' S3' C4' O1' 38.66(19) . . . . ?
C2' S3' C4' C5' 159.2(2) . . . . ?
C4 C5 C6 N1 -1.4(4) . . . . ?
C2 N1 C6 C5 2.4(4) . . . . ?
C1' N1 C6 C5 -173.3(2) . . . . ?
C4' S3' C2' C1' -41.5(2) . . . . ?
C4' O1' C1' N1 113.6(2) . . . . ?
C4' O1' C1' C2' -7.2(3) . . . . ?
C6 N1 C1' O1' -22.1(3) . . . . ?
C2 N1 C1' O1' 162.0(2) . . . . ?
C6 N1 C1' C2' 97.9(3) . . . . ?
C2 N1 C1' C2' -78.1(3) . . . . ?
S3' C2' C1' O1' 35.6(3) . . . . ?
S3' C2' C1' N1 -84.2(2) . . . . ?
O1' C4' C5' O5' -175.8(2) . . . . ?
S3' C4' C5' O5' 65.1(3) . . . . ?
#===END

data_LamHClH2O_RT
_database_code_depnum_ccdc_archive 'CCDC 751366'
#TrackingRef '- CCDC_751365_to_751368.cif'

_audit_creation_date             2008-07-31T17:12:02-00:00
_audit_creation_method           'WinGx routine CIF_UPDATE'

#------------------ CHEMICAL INFORMATION ------------------------------------#

_chemical_formula_weight         283.73
_chemical_absolute_configuration '2R 5S'
_chemical_name_systematic        
;
4-amino-1-[(2R,5S)-2-(hydroxymethyl)-1,
3-oxathiolan-5-yl]-(1H)-pyrimidin-2-one hydrochloride
monohydrate
;

_chemical_name_common            
;
4-amino-1-((2R,5S)-2-(hydroxymethyl)-1, 3-oxathiolan-5-yl)-
(1H)-pyrimidin-2-one hydrochloride monohydrate
;
_chemical_formula_moiety         'C8 H12 N3 O3 S, H2 O, Cl'
_chemical_formula_sum            'C8 H14 Cl N3 O4 S'
_chemical_compound_source        'Polymorph Screening'

#------------------ UNIT CELL INFORMATION -----------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.2927(2)
_cell_length_b                   17.2524(12)
_cell_length_c                   6.8518(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.865(3)
_cell_angle_gamma                90.00
_cell_volume                     618.18(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(1)
_cell_measurement_reflns_used    4343
_cell_measurement_theta_min      2.910
_cell_measurement_theta_max      25.17

#------------------ CRySTAL INFORMATION -------------------------------------#

_exptl_crystal_description       plates
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.584
_exptl_crystal_size_mid          0.098
_exptl_crystal_size_min          0.027
_exptl_crystal_density_diffrn    1.524
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             296
_exptl_absorpt_coefficient_mu    0.485
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
P. Coppens, L. Leiserowitz, D Rabinovich, Acta Cryst.
(1965), 18, 1035-1038
;
_exptl_absorpt_correction_T_min  0.881
_exptl_absorpt_correction_T_max  0.986

#------------------ DATA COLLECTION INFORMATION -----------------------------#

_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_ambient_temperature      298(1)
_diffrn_radiation_monochromator  graphite
_diffrn_reflns_number            7849
_diffrn_reflns_av_R_equivalents  0.0840
_diffrn_reflns_av_sigmaI/netI    0.0648
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         3.83
_diffrn_reflns_theta_max         25.1
_reflns_number_total             1854
_reflns_number_gt                1518
_diffrn_reflns_theta_full        25.1
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.989
_reflns_threshold_expression     >2sigma(I)

#------------------ COMPUTER PROGRAMS USED ----------------------------------#

_computing_data_collection       'Collect (Bruker AxS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_refinement  'SHELxL-97 (Sheldrick, 1997)'

#------------------ REFINEMENT INFORMATION ----------------------------------#

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0354P)^2^+0.0254P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.06(8)
_refine_ls_number_reflns         1854
_refine_ls_number_parameters     172
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0364
_refine_ls_wR_factor_ref         0.0823
_refine_ls_wR_factor_gt          0.0754
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.164
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.041

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.94300(17) 0.16549(6) 0.40462(15) 0.0638(3) Uani 1 1 d . . .
S3' S -0.00291(19) 0.80581(6) 0.05954(16) 0.0555(3) Uani 1 1 d . . .
O1' O -0.2894(4) 0.92404(14) 0.1235(3) 0.0460(6) Uani 1 1 d . . .
O5' O -0.3014(6) 0.90030(18) -0.2971(4) 0.0658(8) Uani 1 1 d . . .
O2 O 0.3535(5) 0.99714(15) 0.4787(4) 0.0557(7) Uani 1 1 d . . .
O1W O 0.4858(6) 0.21966(18) 0.6215(4) 0.0593(8) Uani 1 1 d . . .
N1 N 0.1076(5) 0.98858(16) 0.1757(4) 0.0393(7) Uani 1 1 d . . .
N3 N 0.4538(6) 1.07212(17) 0.2310(4) 0.0425(8) Uani 1 1 d . . .
N4 N 0.5741(6) 1.1496(2) -0.0094(5) 0.0532(9) Uani 1 1 d . . .
C4 C 0.4180(6) 1.0969(2) 0.0418(5) 0.0409(9) Uani 1 1 d . . .
C2' C 0.0630(7) 0.8527(2) 0.2948(5) 0.0503(10) Uani 1 1 d . . .
H2'1 H -0.0099 0.8239 0.3942 0.060 Uiso 1 1 calc R . .
H2'2 H 0.2457 0.8580 0.3369 0.060 Uiso 1 1 calc R . .
C5' C -0.4472(7) 0.8564(3) -0.1806(6) 0.0577(10) Uani 1 1 d . . .
H5'1 H -0.4767 0.8051 -0.2378 0.069 Uiso 1 1 calc R . .
H5'2 H -0.6123 0.8810 -0.1821 0.069 Uiso 1 1 calc R . .
C6 C 0.0640(7) 1.0122(2) -0.0171(5) 0.0438(9) Uani 1 1 d . . .
H6 H -0.0713 0.9904 -0.1021 0.053 Uiso 1 1 calc R . .
C1' C -0.0630(6) 0.9313(2) 0.2595(5) 0.0439(9) Uani 1 1 d . . .
H1' H -0.1044 0.9513 0.3846 0.053 Uiso 1 1 calc R . .
C2 C 0.3077(7) 1.0181(2) 0.3069(5) 0.0432(9) Uani 1 1 d . . .
C5 C 0.2101(7) 1.0657(2) -0.0873(6) 0.0471(9) Uani 1 1 d . . .
H5 H 0.1751 1.0818 -0.2182 0.057 Uiso 1 1 calc R . .
C4' C -0.3173(6) 0.8487(2) 0.0295(5) 0.0443(9) Uani 1 1 d . . .
H4' H -0.4256 0.8166 0.1009 0.053 Uiso 1 1 calc R . .
H3 H 0.591(7) 1.090(2) 0.303(5) 0.053 Uiso 1 1 d . . .
H4Nx H 0.699(7) 1.165(2) 0.086(5) 0.053 Uiso 1 1 d . . .
H4Ny H 0.552(7) 1.164(2) -0.142(5) 0.053 Uiso 1 1 d . . .
H1W H 0.345(8) 0.207(3) 0.546(6) 0.067 Uiso 1 1 d . . .
H2W H 0.608(8) 0.214(3) 0.558(6) 0.067 Uiso 1 1 d . . .
H5'O H -0.442(7) 0.947(2) -0.400(5) 0.067 Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0465(5) 0.0744(8) 0.0673(6) -0.0183(6) -0.0011(4) -0.0003(6)
S3' 0.0505(5) 0.0447(6) 0.0712(7) -0.0048(5) 0.0092(4) 0.0075(5)
O1' 0.0406(14) 0.0411(16) 0.0562(15) 0.0007(12) 0.0068(11) 0.0055(11)
O5' 0.0629(19) 0.077(2) 0.0574(17) 0.0133(14) 0.0076(14) -0.0107(15)
O2 0.0669(17) 0.0553(16) 0.0420(16) 0.0051(13) -0.0005(12) -0.0006(14)
O1W 0.0512(16) 0.071(2) 0.0553(18) -0.0059(15) 0.0060(13) -0.0075(17)
N1 0.0413(16) 0.0379(17) 0.0386(17) 0.0009(13) 0.0053(13) 0.0003(14)
N3 0.0428(17) 0.0383(19) 0.0436(19) 0.0004(15) -0.0025(14) 0.0000(15)
N4 0.0527(18) 0.052(2) 0.0526(19) 0.0031(18) 0.0005(17) -0.0089(17)
C4 0.042(2) 0.038(2) 0.043(2) -0.0007(17) 0.0068(17) 0.0010(18)
C2' 0.055(2) 0.044(2) 0.051(2) 0.0124(19) 0.0044(17) 0.0012(19)
C5' 0.055(2) 0.061(3) 0.057(2) 0.003(2) 0.0081(19) -0.011(2)
C6 0.045(2) 0.046(2) 0.038(2) -0.0014(17) 0.0010(16) -0.0004(18)
C1' 0.044(2) 0.047(2) 0.0417(19) -0.0012(17) 0.0088(16) 0.0039(18)
C2 0.046(2) 0.043(2) 0.039(2) -0.0052(18) 0.0021(17) 0.0045(18)
C5 0.052(2) 0.044(2) 0.044(2) 0.0007(17) 0.0036(18) -0.0078(19)
C4' 0.044(2) 0.039(2) 0.051(2) 0.0046(18) 0.0105(16) -0.0016(17)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S3' C2' 1.789(4) . ?
S3' C4' 1.803(3) . ?
O1' C1' 1.405(4) . ?
O1' C4' 1.449(4) . ?
O5' C5' 1.413(5) . ?
O2 C2 1.219(4) . ?
N1 C6 1.367(4) . ?
N1 C2 1.377(4) . ?
N1 C1' 1.511(5) . ?
N3 C4 1.351(4) . ?
N3 C2 1.365(5) . ?
N4 C4 1.311(5) . ?
C4 C5 1.408(5) . ?
C2' C1' 1.514(5) . ?
C5' C4' 1.502(5) . ?
C6 C5 1.340(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2' S3' C4' 88.04(16) . . ?
C1' O1' C4' 113.1(2) . . ?
C6 N1 C2 121.3(3) . . ?
C6 N1 C1' 122.7(3) . . ?
C2 N1 C1' 116.0(3) . . ?
C4 N3 C2 125.3(3) . . ?
N4 C4 N3 118.4(3) . . ?
N4 C4 C5 124.1(3) . . ?
N3 C4 C5 117.5(3) . . ?
C1' C2' S3' 103.9(2) . . ?
O5' C5' C4' 112.3(3) . . ?
C5 C6 N1 122.1(3) . . ?
O1' C1' N1 107.7(3) . . ?
O1' C1' C2' 109.6(3) . . ?
N1 C1' C2' 111.9(3) . . ?
O2 C2 N3 122.0(3) . . ?
O2 C2 N1 122.7(3) . . ?
N3 C2 N1 115.3(3) . . ?
C6 C5 C4 118.5(3) . . ?
O1' C4' C5' 110.3(3) . . ?
O1' C4' S3' 106.7(2) . . ?
C5' C4' S3' 115.1(3) . . ?
#===END

data_LamHCl_LT
_database_code_depnum_ccdc_archive 'CCDC 751367'
#TrackingRef '- CCDC_751365_to_751368.cif'

_audit_creation_date             2008-07-31T17:12:02-00:00
_audit_creation_method           'WinGx routine CIF_UPDATE'

#------------------ CHEMICAL INFORMATION ------------------------------------#

_chemical_formula_weight         265.72
_chemical_absolute_configuration '2R 5S'
_chemical_name_systematic        
;
4-amino-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]
-(1H)-pyrimidin-2-one hydrochloride
;

_chemical_name_common            
;
4-amino-1-((2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl) -
(1H)-pyrimidin-2-one hydrochloride
;
_chemical_formula_moiety         'C8 H12 N3 O3 S, Cl'
_chemical_formula_sum            'C8 H12 Cl N3 O3 S'
_chemical_compound_source        'Polymorph Screening'

#------------------ UNIT CELL INFORMATION -----------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.6520(3)
_cell_length_b                   11.9240(6)
_cell_length_c                   8.3220(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.760(3)
_cell_angle_gamma                90.00
_cell_volume                     542.35(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3465
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      25.35

#------------------ CRySTAL INFORMATION -------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.432
_exptl_crystal_size_mid          0.098
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    1.627
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             276
_exptl_absorpt_coefficient_mu    0.541
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
P. Coppens, L. Leiserowitz, D Rabinovich, Acta Cryst.
(1965), 18, 1035-1038
;
_exptl_absorpt_correction_T_min  0.833
_exptl_absorpt_correction_T_max  0.944

#------------------ DATA COLLECTION INFORMATION -----------------------------#

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_reflns_number            4562
_diffrn_reflns_av_R_equivalents  0.0848
_diffrn_reflns_av_sigmaI/netI    0.0867
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.05
_diffrn_reflns_theta_full        25.37
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_theta_max         25.37
_diffrn_measured_fraction_theta_max 0.994
_reflns_number_total             1955
_reflns_number_gt                1615
_reflns_threshold_expression     >2sigma(I)

#------------------ COMPUTER PROGRAMS USED ----------------------------------#

_computing_data_collection       'Collect (Bruker AxS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_refinement  'SHELxL-97 (Sheldrick, 1997)'

#------------------ REFINEMENT INFORMATION ----------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0497P)^2^+0.0870P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.04(12)
_refine_ls_number_reflns         1955
_refine_ls_number_parameters     157
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0667
_refine_ls_R_factor_gt           0.0497
_refine_ls_wR_factor_ref         0.1239
_refine_ls_wR_factor_gt          0.1140
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_restrained_S_all      0.994
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.074

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S3' S 0.5520(2) 0.09286(10) -0.13803(13) 0.0336(3) Uani 1 1 d . . .
Cl1 Cl 1.0226(2) 0.25766(10) 0.62943(14) 0.0340(3) Uani 1 1 d . . .
O1' O 0.9296(5) 0.1142(3) 0.1186(4) 0.0295(8) Uani 1 1 d . . .
O2 O 0.4863(6) 0.3053(3) 0.3145(4) 0.0309(8) Uani 1 1 d . . .
O5' O 0.9396(7) -0.0729(3) -0.2272(4) 0.0357(8) Uani 1 1 d . . .
N1 N 0.6139(7) 0.1329(3) 0.2566(5) 0.0263(9) Uani 1 1 d . . .
N4 N 0.1662(7) 0.0020(3) 0.5181(5) 0.0296(9) Uani 1 1 d . . .
C4 C 0.3199(8) 0.0394(4) 0.4368(5) 0.0254(11) Uani 1 1 d . . .
C5 C 0.4586(9) -0.0297(4) 0.3577(6) 0.0295(11) Uani 1 1 d . . .
H5 H 0.4506 -0.1073 0.3649 0.035 Uiso 1 1 calc R . .
N3 N 0.3522(7) 0.1527(3) 0.4275(5) 0.0266(9) Uani 1 1 d . . .
C2 C 0.4853(9) 0.2030(4) 0.3338(6) 0.0244(11) Uani 1 1 d . . .
C4' C 0.8785(8) 0.0782(4) -0.0525(5) 0.0279(10) Uani 1 1 d . . .
H4' H 0.9637 0.1280 -0.1130 0.034 Uiso 1 1 calc R . .
C6 C 0.6026(8) 0.0190(4) 0.2719(6) 0.0284(11) Uani 1 1 d . . .
H6 H 0.6972 -0.0261 0.2215 0.034 Uiso 1 1 calc R . .
C2' C 0.5781(9) 0.2188(4) -0.0188(6) 0.0330(11) Uani 1 1 d . . .
H2'x H 0.6435 0.2793 -0.0725 0.040 Uiso 1 1 calc R . .
H2'y H 0.4201 0.2414 -0.0039 0.040 Uiso 1 1 calc R . .
C1' C 0.7527(8) 0.1890(4) 0.1466(6) 0.0288(10) Uani 1 1 d . . .
H1' H 0.8324 0.2570 0.2006 0.035 Uiso 1 1 calc R . .
C5' C 0.9703(9) -0.0393(4) -0.0597(6) 0.0327(11) Uani 1 1 d . . .
H5'y H 1.1422 -0.0430 -0.0014 0.039 Uiso 1 1 calc R . .
H5'x H 0.8810 -0.0899 -0.0053 0.039 Uiso 1 1 calc R . .
H4Nx H 0.093(9) 0.058(5) 0.572(6) 0.039 Uiso 1 1 d . . .
H4Ny H 0.120(9) -0.083(5) 0.514(7) 0.039 Uiso 1 1 d . . .
H3 H 0.251(9) 0.203(4) 0.484(7) 0.039 Uiso 1 1 d . . .
H5'O H 0.790(11) -0.105(5) -0.257(8) 0.049 Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S3' 0.0329(6) 0.0399(7) 0.0248(6) -0.0029(6) 0.0015(4) 0.0004(6)
Cl1 0.0391(6) 0.0305(6) 0.0332(7) 0.0033(5) 0.0108(5) 0.0052(5)
O1' 0.0292(17) 0.035(2) 0.0232(17) -0.0050(14) 0.0041(12) -0.0014(14)
O2 0.0338(19) 0.0277(19) 0.0286(18) 0.0007(15) 0.0033(14) 0.0012(14)
O5' 0.0380(19) 0.0389(19) 0.032(2) -0.0138(16) 0.0125(16) -0.0071(16)
N1 0.033(2) 0.025(2) 0.021(2) -0.0015(15) 0.0066(16) -0.0008(16)
N4 0.032(2) 0.026(2) 0.031(2) -0.0016(18) 0.0067(17) -0.0026(18)
C4 0.023(2) 0.030(3) 0.020(2) 0.0007(18) -0.0005(18) 0.0016(19)
C5 0.039(3) 0.025(2) 0.023(3) 0.0010(19) 0.005(2) -0.002(2)
N3 0.029(2) 0.027(2) 0.023(2) -0.0023(16) 0.0058(16) -0.0012(17)
C2 0.025(3) 0.024(3) 0.022(3) -0.0017(19) 0.0015(19) 0.0009(19)
C4' 0.031(2) 0.035(3) 0.017(2) -0.0059(19) 0.0044(17) -0.003(2)
C6 0.031(3) 0.026(2) 0.023(3) -0.0019(19) -0.001(2) 0.003(2)
C2' 0.039(3) 0.035(3) 0.025(3) 0.0065(19) 0.008(2) 0.000(2)
C1' 0.032(3) 0.027(2) 0.028(3) -0.0015(19) 0.0071(19) 0.000(2)
C5' 0.034(3) 0.037(3) 0.028(3) -0.007(2) 0.008(2) -0.004(2)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S3' C2' 1.785(5) . ?
S3' C4' 1.809(4) . ?
O1' C1' 1.402(5) . ?
O1' C4' 1.445(5) . ?
O2 C2 1.230(5) . ?
O5' C5' 1.418(6) . ?
O5' H5'O 0.91(6) . ?
N1 C6 1.368(6) . ?
N1 C2 1.370(6) . ?
N1 C1' 1.505(6) . ?
N4 C4 1.308(6) . ?
N4 H4Nx 0.96(6) . ?
N4 H4Ny 1.05(5) . ?
C4 N3 1.368(6) . ?
C4 C5 1.410(7) . ?
C5 C6 1.343(7) . ?
C5 H5 0.9300 . ?
N3 C2 1.355(6) . ?
N3 H3 1.02(6) . ?
C4' C5' 1.500(7) . ?
C4' H4' 0.9800 . ?
C6 H6 0.9300 . ?
C2' C1' 1.517(6) . ?
C2' H2'x 0.9700 . ?
C2' H2'y 0.9700 . ?
C1' H1' 0.9800 . ?
C5' H5'y 0.9700 . ?
C5' H5'x 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2' S3' C4' 86.1(2) . . ?
C1' O1' C4' 112.4(3) . . ?
C5' O5' H5'O 105(4) . . ?
C6 N1 C2 121.3(4) . . ?
C6 N1 C1' 122.8(4) . . ?
C2 N1 C1' 115.8(4) . . ?
C4 N4 H4Nx 115(3) . . ?
C4 N4 H4Ny 120(3) . . ?
H4Nx N4 H4Ny 124(4) . . ?
N4 C4 N3 118.8(4) . . ?
N4 C4 C5 124.3(4) . . ?
N3 C4 C5 116.9(4) . . ?
C6 C5 C4 118.7(4) . . ?
C6 C5 H5 120.7 . . ?
C4 C5 H5 120.7 . . ?
C2 N3 C4 124.9(4) . . ?
C2 N3 H3 118(3) . . ?
C4 N3 H3 117(3) . . ?
O2 C2 N3 122.4(5) . . ?
O2 C2 N1 121.6(5) . . ?
N3 C2 N1 116.0(4) . . ?
O1' C4' C5' 109.4(4) . . ?
O1' C4' S3' 106.6(3) . . ?
C5' C4' S3' 113.8(3) . . ?
O1' C4' H4' 109.0 . . ?
C5' C4' H4' 109.0 . . ?
S3' C4' H4' 109.0 . . ?
C5 C6 N1 121.8(5) . . ?
C5 C6 H6 119.1 . . ?
N1 C6 H6 119.1 . . ?
C1' C2' S3' 104.4(3) . . ?
C1' C2' H2'x 110.9 . . ?
S3' C2' H2'x 110.9 . . ?
C1' C2' H2'y 110.9 . . ?
S3' C2' H2'y 110.9 . . ?
H2'x C2' H2'y 108.9 . . ?
O1' C1' N1 108.8(4) . . ?
O1' C1' C2' 109.0(4) . . ?
N1 C1' C2' 109.7(4) . . ?
O1' C1' H1' 109.8 . . ?
N1 C1' H1' 109.8 . . ?
C2' C1' H1' 109.8 . . ?
O5' C5' C4' 110.3(4) . . ?
O5' C5' H5'y 109.6 . . ?
C4' C5' H5'y 109.6 . . ?
O5' C5' H5'x 109.6 . . ?
C4' C5' H5'x 109.6 . . ?
H5'y C5' H5'x 108.1 . . ?
#===END

data_LamHClH2O_LT
_database_code_depnum_ccdc_archive 'CCDC 751368'
#TrackingRef '- CCDC_751365_to_751368.cif'

_audit_creation_date             2008-07-31T17:12:02-00:00
_audit_creation_method           'WinGx routine CIF_UPDATE'

#------------------ CHEMICAL INFORMATION ------------------------------------#

_chemical_formula_weight         283.73
_chemical_absolute_configuration '2R 5S'
_chemical_name_systematic        
;
4-amino-1-[(2R,5S)-2-(hydroxymethyl)-1,
3-oxathiolan-5-yl]-(1H)-pyrimidin-2-one hydrochloride
monohydrate
;

_chemical_name_common            
;
4-amino-1-((2R,5S)-2-(hydroxymethyl)-1, 3-oxathiolan-5-yl)-
(1H)-pyrimidin-2-one hydrochloride monohydrate
;
_chemical_formula_moiety         'C8 H12 N3 O3 S, H2 O, Cl'
_chemical_formula_sum            'C8 H14 Cl N3 O4 S'
_chemical_compound_source        'Polymorph Screening'

#------------------ UNIT CELL INFORMATION -----------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.2554(1)
_cell_length_b                   17.1944(6)
_cell_length_c                   6.8210(2)
_cell_angle_alpha                90.0000
_cell_angle_beta                 98.774(2)
_cell_angle_gamma                90.0000
_cell_volume                     609.16(3)
_cell_measurement_reflns_used    7369
_cell_measurement_theta_min      2.910
_cell_measurement_theta_max      27.485
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)

#------------------ CRySTAL INFORMATION -------------------------------------#

_exptl_crystal_description       plates
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.584
_exptl_crystal_size_mid          0.098
_exptl_crystal_size_min          0.027
_exptl_crystal_density_diffrn    1.547
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             296
_exptl_absorpt_coefficient_mu    0.492
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
P. Coppens, L. Leiserowitz, D Rabinovich, Acta Cryst.
(1965), 18, 1035-1038
;
_exptl_absorpt_correction_T_min  0.941
_exptl_absorpt_correction_T_max  0.987

#------------------ DATA COLLECTION INFORMATION -----------------------------#

_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_monochromator  graphite
_diffrn_reflns_number            8661
_diffrn_reflns_av_R_equivalents  0.1170
_diffrn_reflns_av_sigmaI/netI    0.0762
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.02
_diffrn_reflns_theta_max         27.45
_reflns_number_total             2547
_reflns_number_gt                2405
_diffrn_reflns_theta_full        27.45
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.985
_reflns_threshold_expression     >2sigma(I)

#------------------ COMPUTER PROGRAMS USED ----------------------------------#

_computing_data_collection       'Collect (Bruker AxS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_refinement  'SHELxL-97 (Sheldrick, 1997)'

#------------------ REFINEMENT INFORMATION ----------------------------------#

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0586P)^2^+0.2721P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.11(8)
_refine_ls_number_reflns         2547
_refine_ls_number_parameters     172
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0500
_refine_ls_wR_factor_ref         0.1166
_refine_ls_wR_factor_gt          0.1137
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.412
_refine_diff_density_min         -0.514
_refine_diff_density_rms         0.086

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 1.05282(14) 0.58873(5) 0.59757(12) 0.0304(2) Uani 1 1 d . . .
S3' S 1.00860(15) 0.22830(5) 0.93833(12) 0.0262(2) Uani 1 1 d . . .
O5' O 1.3045(5) 0.32223(16) 1.2975(4) 0.0302(5) Uani 1 1 d . . .
O1W O 0.4902(5) 0.14489(16) 0.6183(3) 0.0292(5) Uani 1 1 d . . .
O2 O 0.6490(4) 0.42095(15) 0.5182(3) 0.0276(5) Uani 1 1 d . . .
C1' C 1.0683(6) 0.35551(18) 0.7395(5) 0.0223(6) Uani 1 1 d . . .
H1' H 1.1096 0.3764 0.6145 0.027 Uiso 1 1 calc R . .
O1' O 1.2977(4) 0.34752(13) 0.8748(3) 0.0235(5) Uani 1 1 d . . .
N4 N 0.4234(5) 0.57342(18) 1.0126(4) 0.0264(6) Uani 1 1 d . . .
N1 N 0.8958(5) 0.41163(15) 0.8238(4) 0.0206(5) Uani 1 1 d . . .
C4 C 0.5829(6) 0.52139(19) 0.9607(4) 0.0225(6) Uani 1 1 d . . .
N3 N 0.5452(5) 0.49597(16) 0.7693(4) 0.0218(5) Uani 1 1 d . . .
C2 C 0.6951(6) 0.44156(18) 0.6925(5) 0.0218(6) Uani 1 1 d . . .
C5 C 0.7916(6) 0.48890(19) 1.0900(5) 0.0245(6) Uani 1 1 d . . .
H5 H 0.8259 0.5043 1.2221 0.029 Uiso 1 1 calc R . .
C6 C 0.9401(6) 0.43520(19) 1.0187(5) 0.0244(6) Uani 1 1 d . . .
H6 H 1.0766 0.4134 1.1038 0.029 Uiso 1 1 calc R . .
C5' C 1.4554(6) 0.2788(2) 1.1804(5) 0.0277(7) Uani 1 1 d . . .
H5'x H 1.4856 0.2272 1.2369 0.033 Uiso 1 1 calc R . .
H5'y H 1.6212 0.3040 1.1836 0.033 Uiso 1 1 calc R . .
C2' C 0.9437(6) 0.2761(2) 0.7006(5) 0.0252(6) Uani 1 1 d . . .
H2'x H 1.0201 0.2478 0.6012 0.030 Uiso 1 1 calc R . .
H2'y H 0.7600 0.2809 0.6568 0.030 Uiso 1 1 calc R . .
C4' C 1.3265(6) 0.27160(18) 0.9682(4) 0.0221(6) Uani 1 1 d . . .
H4' H 1.4359 0.2396 0.8963 0.026 Uiso 1 1 calc R . .
H4Nx H 0.275(7) 0.583(3) 0.931(6) 0.026 Uiso 1 1 d . . .
H4Ny H 0.444(7) 0.589(3) 1.142(6) 0.026 Uiso 1 1 d . . .
H1W H 0.340(8) 0.130(3) 0.547(6) 0.033 Uiso 1 1 d . . .
H2W H 0.624(8) 0.133(3) 0.557(6) 0.033 Uiso 1 1 d . . .
H3 H 0.391(7) 0.521(3) 0.696(6) 0.026 Uiso 1 1 d . . .
H5'O H 1.407(8) 0.357(3) 1.368(6) 0.033 Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0238(3) 0.0338(4) 0.0326(4) 0.0082(3) 0.0009(3) 0.0006(3)
S3' 0.0266(4) 0.0211(4) 0.0313(4) 0.0015(3) 0.0056(3) -0.0035(3)
O5' 0.0293(12) 0.0326(14) 0.0284(12) -0.0090(10) 0.0034(9) 0.0018(9)
O1W 0.0266(11) 0.0349(14) 0.0257(11) -0.0029(10) 0.0031(9) -0.0027(10)
O2 0.0347(12) 0.0268(12) 0.0204(11) -0.0029(9) 0.0013(8) 0.0004(9)
C1' 0.0235(14) 0.0199(15) 0.0244(15) -0.0026(12) 0.0062(11) 0.0000(11)
O1' 0.0214(10) 0.0200(11) 0.0290(11) 0.0013(9) 0.0035(8) -0.0001(8)
N4 0.0263(13) 0.0272(15) 0.0253(14) -0.0025(11) 0.0032(10) 0.0052(10)
N1 0.0230(12) 0.0173(12) 0.0212(12) -0.0026(10) 0.0027(9) 0.0002(9)
C4 0.0249(14) 0.0219(16) 0.0213(14) 0.0007(12) 0.0052(11) -0.0038(11)
N3 0.0232(12) 0.0202(13) 0.0212(12) 0.0007(10) 0.0012(9) 0.0009(10)
C2 0.0256(15) 0.0174(15) 0.0221(15) 0.0009(11) 0.0028(11) -0.0011(11)
C5 0.0289(15) 0.0244(16) 0.0199(14) -0.0016(12) 0.0024(11) 0.0021(12)
C6 0.0275(16) 0.0231(16) 0.0232(15) 0.0014(12) 0.0057(12) -0.0003(12)
C5' 0.0269(15) 0.0280(17) 0.0286(16) -0.0014(13) 0.0052(11) 0.0053(12)
C2' 0.0297(15) 0.0192(16) 0.0270(15) -0.0039(12) 0.0056(11) -0.0007(12)
C4' 0.0270(14) 0.0151(14) 0.0249(15) -0.0007(12) 0.0064(11) 0.0009(10)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S3' C2' 1.803(3) . ?
S3' C4' 1.812(3) . ?
O5' C5' 1.421(4) . ?
O2 C2 1.229(4) . ?
C1' O1' 1.409(4) . ?
C1' N1 1.497(4) . ?
C1' C2' 1.520(4) . ?
O1' C4' 1.450(4) . ?
N4 C4 1.311(4) . ?
N1 C6 1.375(4) . ?
N1 C2 1.376(4) . ?
C4 N3 1.363(4) . ?
C4 C5 1.414(4) . ?
N3 C2 1.377(4) . ?
C5 C6 1.347(4) . ?
C5' C4' 1.507(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2' S3' C4' 87.63(14) . . ?
O1' C1' N1 108.6(2) . . ?
O1' C1' C2' 109.2(3) . . ?
N1 C1' C2' 112.1(2) . . ?
C1' O1' C4' 113.4(2) . . ?
C6 N1 C2 121.3(3) . . ?
C6 N1 C1' 122.6(3) . . ?
C2 N1 C1' 116.1(2) . . ?
N4 C4 N3 118.2(3) . . ?
N4 C4 C5 124.6(3) . . ?
N3 C4 C5 117.2(3) . . ?
C4 N3 C2 125.1(3) . . ?
O2 C2 N1 122.7(3) . . ?
O2 C2 N3 121.6(3) . . ?
N1 C2 N3 115.7(3) . . ?
C6 C5 C4 118.8(3) . . ?
C5 C6 N1 122.0(3) . . ?
O5' C5' C4' 112.0(3) . . ?
C1' C2' S3' 103.6(2) . . ?
O1' C4' C5' 110.5(3) . . ?
O1' C4' S3' 106.7(2) . . ?
C5' C4' S3' 114.4(2) . . ?