# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2014

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1031620'
_audit_update_record             
;
2014-10-29 deposited with the CCDC.
2014-12-18 downloaded from the CCDC.
;

_audit_creation_date             2014-10-28T17:58:29-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        ?
_chemical_name_common            Lamivudine_Hydrobromide
_chemical_formula_moiety         'C8 H12 N3 O3 S, Br'
_chemical_formula_sum            'C8 H12 Br N3 O3 S'
_chemical_formula_weight         310.18
_chemical_absolute_configuration rm

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_Int_Tables_number      4
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.61900(10)
_cell_length_b                   12.2320(4)
_cell_length_c                   8.3840(3)
_cell_angle_alpha                90
_cell_angle_beta                 104.3040(12)
_cell_angle_gamma                90
_cell_volume                     558.38(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    129
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      26.37
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.384
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.107
_exptl_crystal_density_diffrn    1.845
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             312
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 0 0.134
0 -1 0 0.166
1 0 0 0.207
-1 0 0 0.177
0 0 -1 0.098
0 0 1 0.009

_exptl_special_details           ?

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    3.864
_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  0.318
_exptl_absorpt_correction_T_max  0.683

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

_diffrn_source                   'Enraf Nonius FR590'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_orient_matrix_ub_11      -0.164367
_diffrn_orient_matrix_ub_12      -0.021817
_diffrn_orient_matrix_ub_13      0.015428
_diffrn_orient_matrix_ub_21      -0.068133
_diffrn_orient_matrix_ub_22      0
_diffrn_orient_matrix_ub_23      -0.122048
_diffrn_orient_matrix_ub_31      0.045515
_diffrn_orient_matrix_ub_32      -0.078788
_diffrn_orient_matrix_ub_33      -0.004272
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_reflns_av_R_equivalents  0.077
_diffrn_reflns_number            5387
_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       10
_diffrn_reflns_theta_min         3.01
_diffrn_reflns_theta_max         25.678
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.522
_diffrn_reflns_point_group_measured_fraction_max 0.521
_reflns_number_total             1107
_reflns_number_gt                1075
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_reflns_reduction_process 
;
        Scaled and merged with Sortav
        R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
        R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

#----------------------------------------------------------------------------#
#                   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_solution    'SIR-92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2012)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

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

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0038P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1107
_refine_ls_number_parameters     146
_refine_ls_number_restraints     1
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0245
_refine_ls_R_factor_gt           0.0239
_refine_ls_wR_factor_ref         0.057
_refine_ls_wR_factor_gt          0.0567
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
No quotients, so Flack parameter determined by classical intensity fit
;
_refine_ls_abs_structure_Flack   0.037(12)
_refine_diff_density_max         0.467
_refine_diff_density_min         -0.57
_refine_diff_density_rms         0.109

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.98295(6) 0.48720(6) 0.85584(4) 0.01532(13) Uani 1 d . .
S3' S 0.5618(2) 0.16375(9) 0.37028(13) 0.0175(2) Uani 1 d . .
O2 O 0.4876(6) -0.0486(3) 0.8097(6) 0.0161(8) Uani 1 d . .
O1' O 0.9422(6) 0.1431(3) 0.6236(4) 0.0136(7) Uani 1 d . .
O5' O 0.9449(6) 0.3309(3) 0.2828(4) 0.0181(7) Uani 1 d . .
H5' H 0.8089 0.3585 0.2484 0.027 Uiso 1 calc . .
N1 N 0.6245(7) 0.1204(3) 0.7591(4) 0.0132(8) Uani 1 d . .
N3 N 0.3565(6) 0.0995(3) 0.9289(4) 0.0136(7) Uani 1 d . .
H3 H 0.2836 0.0577 0.9843 0.016 Uiso 1 calc . .
C5 C 0.4747(8) 0.2787(4) 0.8687(5) 0.0162(10) Uani 1 d . .
H5 H 0.47 0.3543 0.8795 0.019 Uiso 1 calc . .
C6 C 0.6177(8) 0.2316(4) 0.7806(5) 0.0132(9) Uani 1 d . .
H6 H 0.7152 0.276 0.7326 0.016 Uiso 1 calc . .
C4 C 0.3314(8) 0.2098(4) 0.9445(5) 0.0137(9) Uani 1 d . .
C2 C 0.4901(8) 0.0500(5) 0.8309(7) 0.0131(12) Uani 1 d . .
N4 N 0.1816(7) 0.2456(3) 1.0298(4) 0.0165(8) Uani 1 d . .
H4A H 0.1013 0.2001 1.0747 0.02 Uiso 1 calc . .
H4B H 0.1633 0.3148 1.041 0.02 Uiso 1 calc . .
C5' C 0.9737(9) 0.2976(4) 0.4489(5) 0.0190(10) Uani 1 d . .
H5'1 H 0.8785 0.345 0.5022 0.023 Uiso 1 calc . .
H5'2 H 1.145 0.3033 0.5079 0.023 Uiso 1 calc . .
C4' C 0.8882(7) 0.1813(3) 0.4533(5) 0.0137(9) Uani 1 d . .
H4' H 0.9762 0.1352 0.3912 0.016 Uiso 1 calc . .
C1' C 0.7651(7) 0.0687(4) 0.6501(5) 0.0153(9) Uani 1 d . .
H1' H 0.847 0.0026 0.7031 0.018 Uiso 1 calc . .
C2' C 0.5934(9) 0.0385(4) 0.4849(5) 0.0164(9) Uani 1 d . .
H2'1 H 0.4357 0.0137 0.4987 0.02 Uiso 1 calc . .
H2'2 H 0.6644 -0.0184 0.4305 0.02 Uiso 1 calc . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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' 1.794(5) . ?
S3' C4' 1.806(4) . ?
O2 C2 1.219(6) . ?
O1' C1' 1.406(5) . ?
O1' C4' 1.461(5) . ?
O5' C5' 1.421(6) . ?
O5' H5' 0.82 . ?
N1 C6 1.374(6) . ?
N1 C2 1.378(7) . ?
N1 C1' 1.488(5) . ?
N3 C4 1.366(6) . ?
N3 C2 1.382(6) . ?
N3 H3 0.86 . ?
C5 C6 1.348(6) . ?
C5 C4 1.420(6) . ?
C5 H5 0.93 . ?
C6 H6 0.93 . ?
C4 N4 1.307(6) . ?
N4 H4A 0.86 . ?
N4 H4B 0.86 . ?
C5' C4' 1.506(6) . ?
C5' H5'1 0.97 . ?
C5' H5'2 0.97 . ?
C4' H4' 0.98 . ?
C1' C2' 1.525(6) . ?
C1' H1' 0.98 . ?
C2' H2'1 0.97 . ?
C2' H2'2 0.97 . ?

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' 86.5(2) . . ?
C1' O1' C4' 112.1(3) . . ?
C5' O5' H5' 109.5 . . ?
C6 N1 C2 121.7(4) . . ?
C6 N1 C1' 122.5(4) . . ?
C2 N1 C1' 115.7(4) . . ?
C4 N3 C2 125.1(4) . . ?
C4 N3 H3 117.5 . . ?
C2 N3 H3 117.5 . . ?
C6 C5 C4 118.2(4) . . ?
C6 C5 H5 120.9 . . ?
C4 C5 H5 120.9 . . ?
C5 C6 N1 122.4(4) . . ?
C5 C6 H6 118.8 . . ?
N1 C6 H6 118.8 . . ?
N4 C4 N3 118.7(4) . . ?
N4 C4 C5 123.9(4) . . ?
N3 C4 C5 117.4(4) . . ?
O2 C2 N1 122.9(6) . . ?
O2 C2 N3 122.2(6) . . ?
N1 C2 N3 115.0(5) . . ?
C4 N4 H4A 120 . . ?
C4 N4 H4B 120 . . ?
H4A N4 H4B 120 . . ?
O5' C5' C4' 109.5(4) . . ?
O5' C5' H5'1 109.8 . . ?
C4' C5' H5'1 109.8 . . ?
O5' C5' H5'2 109.8 . . ?
C4' C5' H5'2 109.8 . . ?
H5'1 C5' H5'2 108.2 . . ?
O1' C4' C5' 109.6(3) . . ?
O1' C4' S3' 106.5(3) . . ?
C5' C4' S3' 113.7(3) . . ?
O1' C4' H4' 109 . . ?
C5' C4' H4' 109 . . ?
S3' C4' H4' 109 . . ?
O1' C1' N1 109.0(3) . . ?
O1' C1' C2' 109.1(3) . . ?
N1 C1' C2' 110.4(3) . . ?
O1' C1' H1' 109.5 . . ?
N1 C1' H1' 109.5 . . ?
C2' C1' H1' 109.5 . . ?
C1' C2' S3' 103.7(3) . . ?
C1' C2' H2'1 111 . . ?
S3' C2' H2'1 111 . . ?
C1' C2' H2'2 111 . . ?
S3' C2' H2'2 111 . . ?
H2'1 C2' H2'2 109 . . ?

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
C4 C5 C6 N1 1.5(6) . . . . ?
C2 N1 C6 C5 -2.0(7) . . . . ?
C1' N1 C6 C5 174.5(4) . . . . ?
C2 N3 C4 N4 173.9(4) . . . . ?
C2 N3 C4 C5 -7.3(7) . . . . ?
C6 C5 C4 N4 -178.4(4) . . . . ?
C6 C5 C4 N3 2.8(6) . . . . ?
C6 N1 C2 O2 177.8(5) . . . . ?
C1' N1 C2 O2 1.0(7) . . . . ?
C6 N1 C2 N3 -2.0(6) . . . . ?
C1' N1 C2 N3 -178.7(4) . . . . ?
C4 N3 C2 O2 -173.0(5) . . . . ?
C4 N3 C2 N1 6.7(6) . . . . ?
C1' O1' C4' C5' 147.0(4) . . . . ?
C1' O1' C4' S3' 23.6(4) . . . . ?
O5' C5' C4' O1' 173.9(3) . . . . ?
O5' C5' C4' S3' -67.0(4) . . . . ?
C2' S3' C4' O1' -38.6(3) . . . . ?
C2' S3' C4' C5' -159.4(4) . . . . ?
C4' O1' C1' N1 -112.0(4) . . . . ?
C4' O1' C1' C2' 8.5(5) . . . . ?
C6 N1 C1' O1' 19.6(5) . . . . ?
C2 N1 C1' O1' -163.7(3) . . . . ?
C6 N1 C1' C2' -100.2(4) . . . . ?
C2 N1 C1' C2' 76.5(5) . . . . ?
O1' C1' C2' S3' -36.9(4) . . . . ?
N1 C1' C2' S3' 82.8(4) . . . . ?
C4' S3' C2' C1' 42.2(3) . . . . ?



# END of CIF

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1031621'
_audit_update_record             
;
2014-10-29 deposited with the CCDC.
2014-12-18 downloaded from the CCDC.
;

_audit_creation_date             2014-10-09T17:03:00-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        ?
_chemical_name_common            Lamivudine_Hydrobromide
_chemical_formula_moiety         'C8 H12 Br1 N3 O3 S1'
_chemical_formula_sum            'C8 H12 Br N3 O3 S'
_chemical_formula_weight         310.18
_chemical_compound_source        'synthesis as described'
_chemical_absolute_configuration rm

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_Int_Tables_number      4
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.689(5)
_cell_length_b                   12.288(5)
_cell_length_c                   8.419(5)
_cell_angle_alpha                90
_cell_angle_beta                 103.897(5)
_cell_angle_gamma                90
_cell_volume                     571.3(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1094
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      25.35
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_crystal_density_diffrn    1.803
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             312
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 1 0.018
0 0 -1 0.007
1 0 0 0.113
-1 0 0 0.075
0 1 0 0.037
0 -1 0 0.012

_exptl_special_details           ?

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    3.776
_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  0.692
_exptl_absorpt_correction_T_max  0.906
_shelx_estimated_absorpt_T_min   0.534
_shelx_estimated_absorpt_T_max   0.895

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

_diffrn_source                   'Enraf Nonius FR590'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_orient_matrix_ub_11      -0.154806
_diffrn_orient_matrix_ub_12      0.005061
_diffrn_orient_matrix_ub_13      -0.08631
_diffrn_orient_matrix_ub_21      0.026339
_diffrn_orient_matrix_ub_22      0.079897
_diffrn_orient_matrix_ub_23      -0.010319
_diffrn_orient_matrix_ub_31      0.090198
_diffrn_orient_matrix_ub_32      -0.014644
_diffrn_orient_matrix_ub_33      -0.086126
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_number            3700
_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       10
_diffrn_reflns_theta_min         2.993
_diffrn_reflns_theta_max         25.346
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.975
_reflns_number_total             2033
_reflns_number_gt                1783
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_reflns_reduction_process 
;
        Scaled and merged with Sortav
        R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
        R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

#----------------------------------------------------------------------------#
#                   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-2012 (Sheldrick, 2012)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

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

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2033
_refine_ls_number_parameters     146
_refine_ls_number_restraints     1
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.046
_refine_ls_R_factor_gt           0.0368
_refine_ls_wR_factor_ref         0.0654
_refine_ls_wR_factor_gt          0.0611
_refine_ls_goodness_of_fit_ref   0.936
_refine_ls_restrained_S_all      0.936
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 652 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.000(7)
_refine_diff_density_max         0.33
_refine_diff_density_min         -0.409
_refine_diff_density_rms         0.068

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
C1' C 0.7445(10) 0.2575(5) 0.8517(7) 0.0383(14) Uani 1 d . .
H1' H 0.6649 0.3234 0.7993 0.046 Uiso 1 calc . .
C2 C 1.0152(11) 0.2746(7) 0.6703(9) 0.0368(19) Uani 1 d . .
C2' C 0.9102(12) 0.2868(5) 1.0154(8) 0.0460(17) Uani 1 d . .
H22' H 0.8399 0.3439 1.0688 0.055 Uiso 1 calc . .
H21' H 1.067 0.3108 1.0025 0.055 Uiso 1 calc . .
C4 C 1.1682(10) 0.1170(5) 0.5550(7) 0.0361(15) Uani 1 d . .
C4' C 0.6159(9) 0.1447(5) 1.0463(7) 0.0407(15) Uani 1 d . .
H4' H 0.5283 0.1911 1.1074 0.049 Uiso 1 calc . .
C5 C 1.0271(10) 0.0481(5) 0.6300(7) 0.0406(16) Uani 1 d . .
H5 H 1.0303 -0.027 0.6176 0.049 Uiso 1 calc . .
C5' C 0.5274(12) 0.0290(5) 1.0501(8) 0.0480(17) Uani 1 d . .
H52' H 0.3586 0.0244 0.9915 0.058 Uiso 1 calc . .
H51' H 0.6203 -0.0188 0.9965 0.058 Uiso 1 calc . .
C6 C 0.8873(11) 0.0951(5) 0.7204(7) 0.0397(15) Uani 1 d . .
H6 H 0.7919 0.051 0.7693 0.048 Uiso 1 calc . .
N1 N 0.8818(7) 0.2053(4) 0.7422(6) 0.0344(12) Uani 1 d . .
N3 N 1.1449(8) 0.2255(4) 0.5732(6) 0.0367(12) Uani 1 d . .
H3 H 1.2182 0.2673 0.5188 0.044 Uiso 1 calc . .
N4 N 1.3152(8) 0.0813(4) 0.4698(6) 0.0467(14) Uani 1 d . .
H4X H 1.3961 0.1265 0.4259 0.056 Uiso 1 calc . .
H4Y H 1.3314 0.0125 0.4574 0.056 Uiso 1 calc . .
O1' O 0.5660(7) 0.1828(4) 0.8775(5) 0.0406(12) Uani 1 d . .
O2 O 1.0196(8) 0.3728(4) 0.6920(7) 0.0460(13) Uani 1 d . .
O5' O 0.5531(7) -0.0043(4) 1.2134(6) 0.0560(13) Uani 1 d . .
H5' H 0.6952 -0.0196 1.2539 0.084 Uiso 1 calc . .
S3' S 0.9367(3) 0.16217(16) 1.1297(2) 0.0522(5) Uani 1 d . .
Br Br 1.48412(10) 0.33614(5) 0.35873(7) 0.0478(2) Uani 1 d . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C1' O1' 1.424(7) . ?
C1' N1 1.489(7) . ?
C1' C2' 1.515(8) . ?
C1' H1' 0.98 . ?
C2 O2 1.220(7) . ?
C2 N3 1.367(8) . ?
C2 N1 1.373(9) . ?
C2' S3' 1.796(6) . ?
C2' H22' 0.97 . ?
C2' H21' 0.97 . ?
C4 N4 1.302(8) . ?
C4 N3 1.351(8) . ?
C4 C5 1.415(8) . ?
C4' O1' 1.458(7) . ?
C4' C5' 1.512(9) . ?
C4' S3' 1.804(5) . ?
C4' H4' 0.98 . ?
C5 C6 1.356(8) . ?
C5 H5 0.93 . ?
C5' O5' 1.408(8) . ?
C5' H52' 0.97 . ?
C5' H51' 0.97 . ?
C6 N1 1.368(8) . ?
C6 H6 0.93 . ?
N3 H3 0.86 . ?
N4 H4X 0.86 . ?
N4 H4Y 0.86 . ?
O5' H5' 0.82 . ?

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
O1' C1' N1 108.4(5) . . ?
O1' C1' C2' 109.0(5) . . ?
N1 C1' C2' 111.2(5) . . ?
O1' C1' H1' 109.4 . . ?
N1 C1' H1' 109.4 . . ?
C2' C1' H1' 109.4 . . ?
O2 C2 N3 122.1(8) . . ?
O2 C2 N1 122.8(8) . . ?
N3 C2 N1 115.1(7) . . ?
C1' C2' S3' 103.8(4) . . ?
C1' C2' H22' 111 . . ?
S3' C2' H22' 111 . . ?
C1' C2' H21' 111 . . ?
S3' C2' H21' 111 . . ?
H22' C2' H21' 109 . . ?
N4 C4 N3 119.2(6) . . ?
N4 C4 C5 123.5(6) . . ?
N3 C4 C5 117.2(5) . . ?
O1' C4' C5' 109.5(5) . . ?
O1' C4' S3' 106.5(4) . . ?
C5' C4' S3' 114.5(5) . . ?
O1' C4' H4' 108.7 . . ?
C5' C4' H4' 108.7 . . ?
S3' C4' H4' 108.7 . . ?
C6 C5 C4 117.9(6) . . ?
C6 C5 H5 121.1 . . ?
C4 C5 H5 121.1 . . ?
O5' C5' C4' 109.7(5) . . ?
O5' C5' H52' 109.7 . . ?
C4' C5' H52' 109.7 . . ?
O5' C5' H51' 109.7 . . ?
C4' C5' H51' 109.7 . . ?
H52' C5' H51' 108.2 . . ?
C5 C6 N1 122.2(6) . . ?
C5 C6 H6 118.9 . . ?
N1 C6 H6 118.9 . . ?
C6 N1 C2 121.5(6) . . ?
C6 N1 C1' 122.8(5) . . ?
C2 N1 C1' 115.7(5) . . ?
C4 N3 C2 125.8(6) . . ?
C4 N3 H3 117.1 . . ?
C2 N3 H3 117.1 . . ?
C4 N4 H4X 120 . . ?
C4 N4 H4Y 120 . . ?
H4X N4 H4Y 120 . . ?
C1' O1' C4' 112.1(4) . . ?
C5' O5' H5' 109.5 . . ?
C2' S3' C4' 86.9(3) . . ?

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
O1' C1' C2' S3' 36.5(5) . . . . ?
N1 C1' C2' S3' -83.0(5) . . . . ?
N4 C4 C5 C6 177.7(6) . . . . ?
N3 C4 C5 C6 -2.8(8) . . . . ?
O1' C4' C5' O5' -174.2(5) . . . . ?
S3' C4' C5' O5' 66.4(6) . . . . ?
C4 C5 C6 N1 -0.8(8) . . . . ?
C5 C6 N1 C2 1.3(9) . . . . ?
C5 C6 N1 C1' -175.0(5) . . . . ?
O2 C2 N1 C6 -177.6(7) . . . . ?
N3 C2 N1 C6 2.0(8) . . . . ?
O2 C2 N1 C1' -1.0(10) . . . . ?
N3 C2 N1 C1' 178.5(5) . . . . ?
O1' C1' N1 C6 -20.1(7) . . . . ?
C2' C1' N1 C6 99.7(6) . . . . ?
O1' C1' N1 C2 163.4(4) . . . . ?
C2' C1' N1 C2 -76.8(6) . . . . ?
N4 C4 N3 C2 -173.8(5) . . . . ?
C5 C4 N3 C2 6.7(8) . . . . ?
O2 C2 N3 C4 173.4(7) . . . . ?
N1 C2 N3 C4 -6.2(9) . . . . ?
N1 C1' O1' C4' 112.6(5) . . . . ?
C2' C1' O1' C4' -8.5(6) . . . . ?
C5' C4' O1' C1' -147.6(5) . . . . ?
S3' C4' O1' C1' -23.3(6) . . . . ?
C1' C2' S3' C4' -42.1(4) . . . . ?
O1' C4' S3' C2' 38.2(4) . . . . ?
C5' C4' S3' C2' 159.4(5) . . . . ?



# END of CIF

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1031622'
_audit_update_record             
;
2014-11-06 deposited with the CCDC.
2014-12-18 downloaded from the CCDC.
;

_audit_creation_date             2014-11-05T17:03:37-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        ?
_chemical_name_common            Lamivudine_Hydrofluoride
_chemical_formula_moiety         'C8 H12 N3 O3 S, F2 H'
_chemical_formula_sum            'C8 H13 F2 N3 O3 S'
_chemical_formula_weight         269.27
_chemical_compound_source        'synthesis as described'
_chemical_absolute_configuration rm

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_Int_Tables_number      4
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.35980(10)
_cell_length_b                   12.0206(4)
_cell_length_c                   8.6306(3)
_cell_angle_alpha                90
_cell_angle_beta                 104.5500(10)
_cell_angle_gamma                90
_cell_volume                     538.22(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2175
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.662
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             280
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 0 0.047
0 1 0 0.069
-1 0 0 0.044
1 0 0 0.058
0 0 -1 0.074
0 0 1 0.072
-1 0 3 0.063
13 -1 -12 0.061
1 0 6 0.07
-1 4 0 0.064
1 2 0 0.076
1 -5 0 0.052

_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.331
_exptl_absorpt_correction_type   none
_shelx_estimated_absorpt_T_min   0.958
_shelx_estimated_absorpt_T_max   0.968

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

_diffrn_source                   'Enraf Nonius FR590'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_orient_matrix_type       'by Bruker AXS Collect from scalepack cell'
_diffrn_orient_matrix_ub_11      0.002546
_diffrn_orient_matrix_ub_12      -0.083175
_diffrn_orient_matrix_ub_13      -0.001278
_diffrn_orient_matrix_ub_21      0.142312
_diffrn_orient_matrix_ub_22      0
_diffrn_orient_matrix_ub_23      0.100351
_diffrn_orient_matrix_ub_31      -0.129983
_diffrn_orient_matrix_ub_32      -0.001629
_diffrn_orient_matrix_ub_33      0.065249
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_reflns_number            2207
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.969
_diffrn_reflns_theta_max         26.366
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_reflns_number_total             2189
_reflns_number_gt                2094
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_reflns_reduction_process 
;
        Scaled and merged with Sortav
        R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
        R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

#----------------------------------------------------------------------------#
#                   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-2012 (Sheldrick, 2012)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

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

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0430P)²+0.1551P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2189
_refine_ls_number_parameters     158
_refine_ls_number_restraints     1
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.034
_refine_ls_R_factor_gt           0.0313
_refine_ls_wR_factor_ref         0.0757
_refine_ls_wR_factor_gt          0.074
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 960 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.04(3)
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.053

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
C1' C 0.2514(5) 0.3738(2) 0.1457(3) 0.0177(6) Uani 1 d . .
H1' H 0.3435 0.4379 0.2089 0.021 Uiso 1 calc . .
C2 C -0.0319(5) 0.3726(2) 0.3265(3) 0.0163(6) Uani 1 d . .
C2' C 0.0665(6) 0.4171(3) -0.0062(3) 0.0209(6) Uani 1 d . .
H2A' H 0.1404 0.4821 -0.0492 0.025 Uiso 1 calc . .
H2B' H -0.1005 0.4388 0.0145 0.025 Uiso 1 calc . .
C4 C -0.1650(5) 0.2037(2) 0.4312(3) 0.0169(6) Uani 1 d . .
C4' C 0.3687(5) 0.2765(2) -0.0669(3) 0.0184(6) Uani 1 d . .
H4' H 0.4662 0.3274 -0.1221 0.022 Uiso 1 calc . .
C5' C 0.4460(6) 0.1577(2) -0.0875(4) 0.0215(6) Uani 1 d . .
H5A' H 0.6285 0.1459 -0.0299 0.026 Uiso 1 calc . .
H5B' H 0.3381 0.1061 -0.0428 0.026 Uiso 1 calc . .
C5 C -0.0122(6) 0.1410(3) 0.3491(3) 0.0177(6) Uani 1 d . .
H5 H -0.0036 0.0622 0.357 0.021 Uiso 1 calc . .
C6 C 0.1204(5) 0.1971(3) 0.2597(3) 0.0175(6) Uani 1 d . .
H6 H 0.2237 0.1565 0.2047 0.021 Uiso 1 calc . .
N1 N 0.1105(4) 0.3102(2) 0.2459(3) 0.0166(5) Uani 1 d . .
N3 N -0.1616(4) 0.3155(2) 0.4193(3) 0.0175(5) Uani 1 d . .
H3 H -0.2483 0.3543 0.4748 0.021 Uiso 1 calc . .
N4 N -0.3053(5) 0.1569(2) 0.5178(3) 0.0201(5) Uani 1 d . .
H4A H -0.396 0.1985 0.5675 0.024 Uiso 1 calc . .
H4B H -0.3087 0.084 0.5262 0.024 Uiso 1 calc . .
O1' O 0.4326(3) 0.30262(19) 0.1035(2) 0.0179(4) Uani 1 d . .
O2 O -0.0426(4) 0.47506(17) 0.3143(3) 0.0203(5) Uani 1 d . .
O5' O 0.4116(4) 0.1369(2) -0.2537(3) 0.0269(5) Uani 1 d . .
H5C' H 0.3002 0.087 -0.2831 0.04 Uiso 1 calc . .
S3' S 0.02681(13) 0.30132(7) -0.14254(8) 0.02241(19) Uani 1 d . .
F1 F 0.5376(4) 0.49689(15) 0.7790(2) 0.0254(4) Uani 1 d . .
F2 F 0.5027(3) 0.42119(16) 0.5287(2) 0.0264(4) Uani 1 d . .
H1 H 0.518(8) 0.458(3) 0.669(5) 0.04 Uiso 1 d . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C1' O1' 1.409(3) . ?
C1' N1 1.493(3) . ?
C1' C2' 1.523(4) . ?
C2 O2 1.236(3) . ?
C2 N3 1.369(3) . ?
C2 N1 1.377(4) . ?
C2' S3' 1.800(3) . ?
C4 N4 1.313(4) . ?
C4 N3 1.349(4) . ?
C4 C5 1.425(4) . ?
C4' O1' 1.457(3) . ?
C4' C5' 1.510(4) . ?
C4' S3' 1.809(3) . ?
C5' O5' 1.421(4) . ?
C5 C6 1.353(4) . ?
C6 N1 1.364(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
O1' C1' N1 108.7(2) . . ?
O1' C1' C2' 109.1(2) . . ?
N1 C1' C2' 111.0(2) . . ?
O2 C2 N3 122.0(3) . . ?
O2 C2 N1 121.3(3) . . ?
N3 C2 N1 116.7(2) . . ?
C1' C2' S3' 104.1(2) . . ?
N4 C4 N3 119.4(3) . . ?
N4 C4 C5 122.7(3) . . ?
N3 C4 C5 117.9(2) . . ?
O1' C4' C5' 108.7(2) . . ?
O1' C4' S3' 106.79(18) . . ?
C5' C4' S3' 113.4(2) . . ?
O5' C5' C4' 108.4(2) . . ?
C6 C5 C4 118.0(3) . . ?
C5 C6 N1 122.1(3) . . ?
C6 N1 C2 120.8(2) . . ?
C6 N1 C1' 123.1(2) . . ?
C2 N1 C1' 116.1(2) . . ?
C4 N3 C2 124.2(2) . . ?
C1' O1' C4' 112.9(2) . . ?
C2' S3' C4' 87.08(13) . . ?



# END of CIF
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1031623'
_audit_update_record             
;
2014-11-06 deposited with the CCDC.
2014-12-18 downloaded from the CCDC.
;

_audit_creation_date             2014-11-05T16:04:10-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
 ?
;
_chemical_name_common            Lamivudine_Hydrofluoride
_chemical_formula_moiety         'C8  H12  N3  O3  S,  F2  H'
_chemical_formula_sum            'C8  H13  F2  N3  O3  S'
_chemical_formula_weight         269.27
_chemical_compound_source        'synthesis as described'
_chemical_absolute_configuration rm

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_Int_Tables_number      4
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.43490(10)
_cell_length_b                   12.0714(3)
_cell_length_c                   8.6515(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.854(2)
_cell_angle_gamma                90
_cell_volume                     551.09(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1181
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      26.37
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.14
_exptl_crystal_density_diffrn    1.623
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             280
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 0 0.048
0 -1 0 0.09
1 0 0 0.086
-1 0 0 0.089
0 0 1 0.103
0 0 -1 0.074
-2 -3 0 0.079
6 1 -6 0.089

_exptl_special_details           ?

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.324
_exptl_absorpt_correction_type   none
_shelx_estimated_absorpt_T_min   0.944
_shelx_estimated_absorpt_T_max   0.956

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

_diffrn_source                   'Enraf Nonius FR590'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_orient_matrix_ub_11      -0.116146
_diffrn_orient_matrix_ub_12      0.064619
_diffrn_orient_matrix_ub_13      -0.002886
_diffrn_orient_matrix_ub_21      0.14846
_diffrn_orient_matrix_ub_22      0.047959
_diffrn_orient_matrix_ub_23      0.048472
_diffrn_orient_matrix_ub_31      0.019587
_diffrn_orient_matrix_ub_32      0.019671
_diffrn_orient_matrix_ub_33      -0.108697
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_reflns_number            2189
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.954
_diffrn_reflns_theta_max         26.376
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.962
_reflns_number_total             2174
_reflns_number_gt                2043
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_reflns_reduction_process 
;
        Scaled and merged with Sortav
        R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
        R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;


#----------------------------------------------------------------------------#
#                   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-2012 (Sheldrick, 2012)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

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

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0468P)²+0.0909P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.069(9)
_refine_ls_number_reflns         2174
_refine_ls_number_parameters     159
_refine_ls_number_restraints     1
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0341
_refine_ls_R_factor_gt           0.0308
_refine_ls_wR_factor_ref         0.0803
_refine_ls_wR_factor_gt          0.0772
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 901 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.06(3)
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.039

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F -0.4955(4) 0.6998(2) 0.5301(3) 0.0654(6) Uani 1 d . .
F2 F -0.4579(5) 0.77687(18) 0.7758(2) 0.0607(6) Uani 1 d . .
H1A H -0.480(9) 0.741(4) 0.673(6) 0.091 Uiso 1 d . .
C1' C 0.2472(5) 0.6539(2) 0.1445(3) 0.0359(6) Uani 1 d . .
H1' H 0.3354 0.7167 0.2054 0.043 Uiso 1 calc . .
C2 C -0.0335(5) 0.6544(2) 0.3259(3) 0.0342(6) Uani 1 d . .
C2' C 0.0681(6) 0.6968(3) -0.0061(4) 0.0468(7) Uani 1 d . .
H2A' H 0.14 0.7605 -0.0479 0.056 Uiso 1 calc . .
H2B' H -0.0938 0.7177 0.0139 0.056 Uiso 1 calc . .
C4 C -0.1670(5) 0.4866(2) 0.4312(3) 0.0344(6) Uani 1 d . .
C4' C 0.3670(5) 0.5563(2) -0.0655(3) 0.0373(6) Uani 1 d . .
H4' H 0.4629 0.6056 -0.1194 0.045 Uiso 1 calc . .
C5 C -0.0153(6) 0.4242(2) 0.3504(3) 0.0387(6) Uani 1 d . .
H5 H -0.0069 0.3474 0.3591 0.046 Uiso 1 calc . .
C5' C 0.4434(7) 0.4389(3) -0.0856(4) 0.0467(7) Uani 1 d . .
H5A' H 0.6186 0.4277 -0.0293 0.056 Uiso 1 calc . .
H5B' H 0.3386 0.3887 -0.0414 0.056 Uiso 1 calc . .
C6 C 0.1165(5) 0.4790(2) 0.2606(3) 0.0353(6) Uani 1 d . .
H6 H 0.2168 0.4388 0.2074 0.042 Uiso 1 calc . .
N1 N 0.1073(4) 0.5914(2) 0.2455(2) 0.0329(5) Uani 1 d . .
N3 N -0.1634(4) 0.5977(2) 0.4179(2) 0.0349(5) Uani 1 d . .
H3 H -0.2489 0.6357 0.471 0.052 Uiso 1 calc . .
N4 N -0.3057(5) 0.4406(2) 0.5184(3) 0.0446(6) Uani 1 d . .
H4A H -0.3936 0.4814 0.5666 0.067 Uiso 1 calc . .
H4B H -0.3089 0.3697 0.5274 0.067 Uiso 1 calc . .
O1' O 0.4263(3) 0.58315(19) 0.10259(19) 0.0381(4) Uani 1 d . .
O2 O -0.0428(4) 0.75590(16) 0.3139(3) 0.0451(5) Uani 1 d . .
O5' O 0.4137(5) 0.4165(2) -0.2494(3) 0.0605(7) Uani 1 d . .
H5C' H 0.3012 0.3705 -0.2784 0.091 Uiso 1 calc . .
S3' S 0.03324(14) 0.58195(9) -0.14142(8) 0.0508(2) Uani 1 d . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
F1 H1A 1.31(5) . ?
F2 H1A 0.97(5) . ?
C1' O1' 1.407(3) . ?
C1' N1 1.493(3) . ?
C1' C2' 1.519(4) . ?
C1' H1' 0.98 . ?
C2 O2 1.229(3) . ?
C2 N3 1.367(3) . ?
C2 N1 1.380(3) . ?
C2' S3' 1.795(4) . ?
C2' H2A' 0.97 . ?
C2' H2B' 0.97 . ?
C4 N4 1.311(4) . ?
C4 N3 1.347(4) . ?
C4 C5 1.418(4) . ?
C4' O1' 1.449(3) . ?
C4' C5' 1.499(4) . ?
C4' S3' 1.802(3) . ?
C4' H4' 0.98 . ?
C5 C6 1.349(4) . ?
C5 H5 0.93 . ?
C5' O5' 1.414(4) . ?
C5' H5A' 0.97 . ?
C5' H5B' 0.97 . ?
C6 N1 1.362(4) . ?
C6 H6 0.93 . ?
N3 H3 0.86 . ?
N4 H4A 0.86 . ?
N4 H4B 0.86 . ?
O5' H5C' 0.82 . ?

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
O1' C1' N1 108.9(2) . . ?
O1' C1' C2' 109.1(2) . . ?
N1 C1' C2' 111.3(2) . . ?
O1' C1' H1' 109.2 . . ?
N1 C1' H1' 109.2 . . ?
C2' C1' H1' 109.2 . . ?
O2 C2 N3 122.1(2) . . ?
O2 C2 N1 121.6(3) . . ?
N3 C2 N1 116.3(2) . . ?
C1' C2' S3' 104.0(2) . . ?
C1' C2' H2A' 111 . . ?
S3' C2' H2A' 111 . . ?
C1' C2' H2B' 111 . . ?
S3' C2' H2B' 111 . . ?
H2A' C2' H2B' 109 . . ?
N4 C4 N3 119.5(2) . . ?
N4 C4 C5 122.8(3) . . ?
N3 C4 C5 117.7(2) . . ?
O1' C4' C5' 109.1(2) . . ?
O1' C4' S3' 106.85(17) . . ?
C5' C4' S3' 113.7(2) . . ?
O1' C4' H4' 109 . . ?
C5' C4' H4' 109 . . ?
S3' C4' H4' 109 . . ?
C6 C5 C4 118.3(3) . . ?
C6 C5 H5 120.8 . . ?
C4 C5 H5 120.8 . . ?
O5' C5' C4' 109.2(3) . . ?
O5' C5' H5A' 109.8 . . ?
C4' C5' H5A' 109.8 . . ?
O5' C5' H5B' 109.8 . . ?
C4' C5' H5B' 109.8 . . ?
H5A' C5' H5B' 108.3 . . ?
C5 C6 N1 122.1(3) . . ?
C5 C6 H6 119 . . ?
N1 C6 H6 119 . . ?
C6 N1 C2 120.8(2) . . ?
C6 N1 C1' 123.2(2) . . ?
C2 N1 C1' 115.9(2) . . ?
C4 N3 C2 124.6(2) . . ?
C4 N3 H3 117.7 . . ?
C2 N3 H3 117.7 . . ?
C4 N4 H4A 120 . . ?
C4 N4 H4B 120 . . ?
H4A N4 H4B 120 . . ?
C1' O1' C4' 113.2(2) . . ?
C5' O5' H5C' 109.5 . . ?
C2' S3' C4' 87.43(14) . . ?

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
O1' C1' C2' S3' 35.7(3) . . . . ?
N1 C1' C2' S3' -84.5(2) . . . . ?
N4 C4 C5 C6 178.5(3) . . . . ?
N3 C4 C5 C6 -2.3(4) . . . . ?
O1' C4' C5' O5' -173.1(2) . . . . ?
S3' C4' C5' O5' 67.7(3) . . . . ?
C4 C5 C6 N1 -0.1(4) . . . . ?
C5 C6 N1 C2 1.8(4) . . . . ?
C5 C6 N1 C1' -178.8(3) . . . . ?
O2 C2 N1 C6 179.7(3) . . . . ?
N3 C2 N1 C6 -0.9(4) . . . . ?
O2 C2 N1 C1' 0.3(4) . . . . ?
N3 C2 N1 C1' 179.6(2) . . . . ?
O1' C1' N1 C6 -13.6(3) . . . . ?
C2' C1' N1 C6 106.7(3) . . . . ?
O1' C1' N1 C2 165.9(2) . . . . ?
C2' C1' N1 C2 -73.8(3) . . . . ?
N4 C4 N3 C2 -177.5(2) . . . . ?
C5 C4 N3 C2 3.3(4) . . . . ?
O2 C2 N3 C4 177.6(3) . . . . ?
N1 C2 N3 C4 -1.7(4) . . . . ?
N1 C1' O1' C4' 111.9(2) . . . . ?
C2' C1' O1' C4' -9.8(3) . . . . ?
C5' C4' O1' C1' -144.1(2) . . . . ?
S3' C4' O1' C1' -20.7(3) . . . . ?
C1' C2' S3' C4' -40.0(2) . . . . ?
O1' C4' S3' C2' 35.6(2) . . . . ?
C5' C4' S3' C2' 156.0(2) . . . . ?



# END of CIF
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_clohcl
_database_code_depnum_ccdc_archive 'CCDC 1036386'
_audit_update_record             
;
2014-11-26 deposited with the CCDC.
2014-12-18 downloaded from the CCDC.
;

_audit_creation_date             2013-03-07T10:18:56-00:00
_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            'lamivudine 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                   6.0770(7)
_cell_length_b                   16.324(2)
_cell_length_c                   6.3440(7)
_cell_angle_alpha                90
_cell_angle_beta                 115.577(8)
_cell_angle_gamma                90
_cell_volume                     567.66(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    911
_cell_measurement_theta_min      3.395
_cell_measurement_theta_max      25.35

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

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.604
_exptl_crystal_size_mid          0.347
_exptl_crystal_size_min          0.109
_exptl_crystal_density_diffrn    1.555
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             276
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 0 0.047
0 1 0 0.062
1 0 0 0.352
-1 0 0 0.252
1 0 1 0.47
-1 0 -1 0.444
1 0 -1 0.024
-1 0 1 0.027

_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.516
_exptl_absorpt_correction_type   none

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

_diffrn_source                   'Enraf Nonius FR590'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_orient_matrix_type       'by Bruker AXS Collect from scalepack cell'
_diffrn_orient_matrix_ub_11      0.172845
_diffrn_orient_matrix_ub_12      -0.97596E-2
_diffrn_orient_matrix_ub_13      0.115209
_diffrn_orient_matrix_ub_21      0.579782E-1
_diffrn_orient_matrix_ub_22      0.226525E-1
_diffrn_orient_matrix_ub_23      -0.113647
_diffrn_orient_matrix_ub_31      0.66618E-2
_diffrn_orient_matrix_ub_32      0.560736E-1
_diffrn_orient_matrix_ub_33      0.65963E-1
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_reflns_av_R_equivalents  0.0446
_diffrn_reflns_av_unetI/netI     0.0622
_diffrn_reflns_number            4301
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         3.88
_diffrn_reflns_theta_max         24.7
_diffrn_reflns_theta_full        24.7
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.966
_reflns_number_total             1731
_reflns_number_gt                1356
_reflns_threshold_expression     >2σ(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, 2008)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

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

_refine_special_details          
;
 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 > 2σ(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.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1036P)²+0.1924P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1731
_refine_ls_number_parameters     146
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0857
_refine_ls_R_factor_gt           0.0635
_refine_ls_wR_factor_ref         0.1754
_refine_ls_wR_factor_gt          0.1566
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.032
_refine_ls_shift/su_mean         0.002
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.16(18)
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.075

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.8488(3) -0.09189(10) 1.1628(3) 0.0633(5) Uani 1 1 d . . .
S3' S 1.0213(5) 0.29795(13) 0.2737(4) 0.0798(7) Uani 1 1 d . . .
O1' O 0.8725(9) 0.1471(3) 0.1339(7) 0.0570(12) Uani 1 1 d . . .
N3 N 0.7397(11) 0.0002(3) 0.6886(9) 0.0541(13) Uani 1 1 d . . .
H3 H 0.7977 -0.024 0.822 0.065 Uiso 1 1 calc R . .
N1 N 0.7863(10) 0.0908(3) 0.4288(9) 0.0493(13) Uani 1 1 d . . .
O2 O 1.1007(10) 0.0649(3) 0.7848(9) 0.0678(13) Uani 1 1 d . . .
O5' O 0.4700(13) 0.2525(5) -0.0338(14) 0.105(2) Uani 1 1 d . . .
H5'O H 0.4047 0.2977 -0.0597 0.158 Uiso 1 1 calc R . .
C6 C 0.5537(13) 0.0776(4) 0.2757(12) 0.0540(16) Uani 1 1 d . . .
H6 H 0.4898 0.1056 0.1341 0.065 Uiso 1 1 calc R . .
C2 C 0.8944(13) 0.0537(4) 0.6444(12) 0.0517(15) Uani 1 1 d . . .
C4 C 0.5101(13) -0.0162(4) 0.5411(12) 0.0531(15) Uani 1 1 d . . .
N4 N 0.3862(13) -0.0693(4) 0.6058(11) 0.0706(17) Uani 1 1 d . . .
H4NX H 0.4546 -0.0924 0.7408 0.085 Uiso 1 1 calc R . .
H4NY H 0.2375 -0.0808 0.5129 0.085 Uiso 1 1 calc R . .
C5 C 0.4104(12) 0.0243(4) 0.3230(11) 0.0546(15) Uani 1 1 d . . .
H5 H 0.2504 0.0147 0.2148 0.065 Uiso 1 1 calc R . .
C2' C 0.9185(16) 0.2367(4) 0.4468(13) 0.068(2) Uani 1 1 d . . .
H2'X H 1.0188 0.2455 0.6122 0.081 Uiso 1 1 calc R . .
H2'Y H 0.75 0.2489 0.4117 0.081 Uiso 1 1 calc R . .
C1' C 0.9448(12) 0.1497(4) 0.3762(11) 0.0524(15) Uani 1 1 d . . .
H1' H 1.1156 0.1325 0.4585 0.063 Uiso 1 1 calc R . .
C4' C 0.8837(13) 0.2256(4) 0.0374(12) 0.0580(17) Uani 1 1 d . . .
H4' H 0.9897 0.2207 -0.0425 0.07 Uiso 1 1 calc R . .
C5' C 0.6344(16) 0.2476(7) -0.1399(14) 0.082(2) Uani 1 1 d . . .
H5'X H 0.6396 0.2999 -0.2102 0.098 Uiso 1 1 calc R . .
H5'Y H 0.5772 0.2065 -0.2625 0.098 Uiso 1 1 calc R . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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(7) . ?
S3' C4' 1.805(7) . ?
O1' C1' 1.405(7) . ?
O1' C4' 1.435(8) . ?
N3 C4 1.329(8) . ?
N3 C2 1.398(9) . ?
N3 H3 0.86 . ?
N1 C6 1.343(9) . ?
N1 C2 1.376(8) . ?
N1 C1' 1.497(8) . ?
O2 C2 1.198(8) . ?
O5' C5' 1.428(10) . ?
O5' H5'O 0.82 . ?
C6 C5 1.353(10) . ?
C6 H6 0.93 . ?
C4 N4 1.324(9) . ?
C4 C5 1.413(10) . ?
N4 H4NX 0.86 . ?
N4 H4NY 0.86 . ?
C5 H5 0.93 . ?
C2' C1' 1.519(10) . ?
C2' H2'X 0.97 . ?
C2' H2'Y 0.97 . ?
C1' H1' 0.98 . ?
C4' C5' 1.489(11) . ?
C4' H4' 0.98 . ?
C5' H5'X 0.97 . ?
C5' H5'Y 0.97 . ?

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' 89.1(3) . . ?
C1' O1' C4' 113.0(5) . . ?
C4 N3 C2 125.3(5) . . ?
C4 N3 H3 117.4 . . ?
C2 N3 H3 117.4 . . ?
C6 N1 C2 123.4(6) . . ?
C6 N1 C1' 121.3(5) . . ?
C2 N1 C1' 115.3(5) . . ?
C5' O5' H5'O 109.5 . . ?
N1 C6 C5 121.4(6) . . ?
N1 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
O2 C2 N1 124.7(6) . . ?
O2 C2 N3 121.7(6) . . ?
N1 C2 N3 113.6(6) . . ?
N3 C4 N4 118.6(6) . . ?
N3 C4 C5 118.1(6) . . ?
N4 C4 C5 123.3(7) . . ?
C4 N4 H4NX 120 . . ?
C4 N4 H4NY 120 . . ?
H4NX N4 H4NY 120 . . ?
C6 C5 C4 118.2(6) . . ?
C6 C5 H5 120.9 . . ?
C4 C5 H5 120.9 . . ?
C1' C2' S3' 103.5(4) . . ?
C1' C2' H2'X 111.1 . . ?
S3' C2' H2'X 111.1 . . ?
C1' C2' H2'Y 111.1 . . ?
S3' C2' H2'Y 111.1 . . ?
H2'X C2' H2'Y 109 . . ?
O1' C1' N1 107.3(5) . . ?
O1' C1' C2' 109.1(5) . . ?
N1 C1' C2' 112.0(5) . . ?
O1' C1' H1' 109.5 . . ?
N1 C1' H1' 109.5 . . ?
C2' C1' H1' 109.5 . . ?
O1' C4' C5' 108.5(6) . . ?
O1' C4' S3' 108.7(4) . . ?
C5' C4' S3' 115.2(6) . . ?
O1' C4' H4' 108.1 . . ?
C5' C4' H4' 108.1 . . ?
S3' C4' H4' 108.1 . . ?
O5' C5' C4' 110.4(7) . . ?
O5' C5' H5'X 109.6 . . ?
C4' C5' H5'X 109.6 . . ?
O5' C5' H5'Y 109.6 . . ?
C4' C5' H5'Y 109.6 . . ?
H5'X C5' H5'Y 108.1 . . ?

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
C2 N1 C6 C5 -1.6(10) . . . . ?
C1' N1 C6 C5 180.0(6) . . . . ?
C6 N1 C2 O2 -179.4(7) . . . . ?
C1' N1 C2 O2 -0.9(9) . . . . ?
C6 N1 C2 N3 0.5(9) . . . . ?
C1' N1 C2 N3 179.0(5) . . . . ?
C4 N3 C2 O2 -179.1(7) . . . . ?
C4 N3 C2 N1 1.0(9) . . . . ?
C2 N3 C4 N4 179.0(6) . . . . ?
C2 N3 C4 C5 -1.3(10) . . . . ?
N1 C6 C5 C4 1.2(10) . . . . ?
N3 C4 C5 C6 0.1(9) . . . . ?
N4 C4 C5 C6 179.8(7) . . . . ?
C4' S3' C2' C1' 36.4(6) . . . . ?
C4' O1' C1' N1 143.4(5) . . . . ?
C4' O1' C1' C2' 21.9(7) . . . . ?
C6 N1 C1' O1' -32.8(8) . . . . ?
C2 N1 C1' O1' 148.6(5) . . . . ?
C6 N1 C1' C2' 86.9(7) . . . . ?
C2 N1 C1' C2' -91.7(7) . . . . ?
S3' C2' C1' O1' -39.9(7) . . . . ?
S3' C2' C1' N1 -158.5(5) . . . . ?
C1' O1' C4' C5' -119.6(6) . . . . ?
C1' O1' C4' S3' 6.4(6) . . . . ?
C2' S3' C4' O1' -26.0(5) . . . . ?
C2' S3' C4' C5' 95.9(6) . . . . ?
O1' C4' C5' O5' 60.8(9) . . . . ?
S3' C4' C5' O5' -61.2(9) . . . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
