#------------------------------------------------------------------------------
#$Date: 2016-03-26 22:53:30 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180522 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/91/7219137.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7219137
loop_
_publ_author_name
'Tenorio Clavijo, Juan Carlos'
'Guimarães, Freddy Fernandes'
'Ellena, Javier'
'Martins, Felipe Terra'
_publ_section_title
;
 Isostructurality and the conformational role of the
 2′,3′-moieties in the diversity of lamivudine crystal forms
 probed in halide salts
;
_journal_issue                   28
_journal_name_full               CrystEngComm
_journal_page_first              5187
_journal_paper_doi               10.1039/C4CE02373K
_journal_volume                  17
_journal_year                    2015
_chemical_absolute_configuration '2R 5S'
_chemical_compound_source        'Polymorph Screening'
_chemical_formula_moiety         'C8 H12 N3 O3 S, Cl'
_chemical_formula_sum            'C8 H12 Cl N3 O3 S'
_chemical_formula_weight         265.72
_chemical_name_common            'lamivudine hydrochloride'
_chemical_name_systematic
;
 4-amino-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-(1H)-pyrimidin-2-one hydrochloride
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-03-07T10:18:56-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2014-11-26 deposited with the CCDC.
2014-12-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 115.577(8)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.0770(7)
_cell_length_b                   16.324(2)
_cell_length_c                   6.3440(7)
_cell_measurement_reflns_used    911
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.35
_cell_measurement_theta_min      3.395
_cell_volume                     567.66(12)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_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_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0446
_diffrn_reflns_av_unetI/netI     0.0622
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            4301
_diffrn_reflns_theta_full        24.7
_diffrn_reflns_theta_max         24.7
_diffrn_reflns_theta_min         3.88
_diffrn_source                   'Enraf Nonius FR590'
_exptl_absorpt_coefficient_mu    0.516
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.555
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             276
_exptl_crystal_size_max          0.604
_exptl_crystal_size_mid          0.347
_exptl_crystal_size_min          0.109
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.075
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.16(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         1731
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0857
_refine_ls_R_factor_gt           0.0635
_refine_ls_shift/su_max          0.032
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1036P)²+0.1924P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1566
_refine_ls_wR_factor_ref         0.1754
_reflns_number_gt                1356
_reflns_number_total             1731
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c4ce02373k1.cif
_cod_data_source_block           clohcl
_cod_depositor_comments
'Adding full bibliography for 7219133--7219137.cif.'
_cod_original_sg_symbol_H-M      P21
_cod_database_code               7219137
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
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
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
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 0.0722(11) 0.0543(9) 0.0635(10) 0.0073(8) 0.0294(9) -0.0026(8)
S3' 0.1156(19) 0.0642(11) 0.0770(13) -0.0123(9) 0.0581(14) -0.0295(11)
O1' 0.077(3) 0.049(2) 0.052(3) -0.0014(19) 0.034(2) 0.000(2)
N3 0.057(3) 0.054(3) 0.047(3) 0.008(2) 0.018(3) 0.000(2)
N1 0.049(3) 0.045(3) 0.054(3) 0.000(2) 0.022(3) 0.001(2)
O2 0.064(3) 0.074(3) 0.054(3) 0.009(2) 0.014(3) -0.005(3)
O5' 0.089(4) 0.118(6) 0.122(5) 0.058(5) 0.058(4) 0.041(4)
C6 0.055(4) 0.057(4) 0.047(4) 0.011(3) 0.019(3) 0.010(3)
C2 0.055(4) 0.047(4) 0.047(4) 0.005(3) 0.017(3) 0.001(3)
C4 0.060(4) 0.046(3) 0.055(4) 0.000(3) 0.026(4) 0.002(3)
N4 0.065(4) 0.076(4) 0.060(4) 0.014(3) 0.016(3) -0.005(3)
C5 0.050(4) 0.053(4) 0.053(4) 0.004(3) 0.015(3) 0.004(3)
C2' 0.099(6) 0.055(4) 0.063(4) -0.023(3) 0.047(4) -0.025(4)
C1' 0.055(4) 0.053(4) 0.048(3) 0.008(3) 0.021(3) -0.003(3)
C4' 0.070(5) 0.055(4) 0.057(4) 0.004(3) 0.035(4) -0.001(3)
C5' 0.077(6) 0.100(7) 0.071(5) 0.024(5) 0.035(5) 0.003(5)
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_
_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
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
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_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
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_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
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)
