#------------------------------------------------------------------------------
#$Date: 2016-03-26 16:45:39 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180354 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/23/7202352.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_7202352
loop_
_publ_author_name
'Bhatt, Prashant M.'
'Desiraju, Gautam R.'
_publ_section_title
;
 Co-crystal formation and the determination of absolute configuration
;
_journal_issue                   12
_journal_name_full               CrystEngComm
_journal_page_first              1747
_journal_paper_doi               10.1039/b810643f
_journal_volume                  10
_journal_year                    2008
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C10 H13 N5 O4, C8 H11 N3 O3 S, H2 O'
_chemical_formula_sum            'C18 H26 N8 O8 S'
_chemical_formula_weight         514.53
_chemical_melting_point          100
_chemical_name_common            'Lamivudine + Zidovudine hydrate'
_chemical_name_systematic        'Lamivudine + Zidovudine hydrate'
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_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_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.506(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.6899(10)
_cell_length_b                   7.2501(9)
_cell_length_c                   18.504(2)
_cell_measurement_reflns_used    4965
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.00
_cell_measurement_theta_min      2.20
_cell_volume                     1164.7(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_av_sigmaI/netI    0.0285
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            11952
_diffrn_reflns_theta_full        26.06
_diffrn_reflns_theta_max         26.06
_diffrn_reflns_theta_min         1.10
_exptl_absorpt_coefficient_mu    0.201
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             540
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     365
_refine_ls_number_reflns         4557
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0374
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0649P)²+0.0862P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0965
_refine_ls_wR_factor_ref         0.0993
_reflns_number_gt                4206
_reflns_number_total             4557
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b810643f.txt
_cod_data_source_block           cciv
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               7202352
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
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.70005(6) 0.59785(9) 0.45289(3) 0.04971(16) Uani 1 1 d . . .
N4 N 0.97612(19) 1.0053(3) 0.09772(8) 0.0407(4) Uani 1 1 d . . .
O1 O 0.92366(16) 1.0969(2) 0.21593(7) 0.0408(3) Uani 1 1 d . . .
N5 N 1.0365(2) 0.9829(3) -0.02242(9) 0.0465(5) Uani 1 1 d . . .
O4 O 1.2790(2) 0.9610(4) -0.05779(9) 0.0664(6) Uani 1 1 d . . .
O7 O 0.25525(17) 0.3468(3) 0.34142(9) 0.0622(5) Uani 1 1 d . . .
C16 C 0.3605(2) 0.3707(3) 0.29945(11) 0.0411(5) Uani 1 1 d . . .
N7 N 0.33507(19) 0.4040(3) 0.22815(10) 0.0483(5) Uani 1 1 d . . .
O5 O 0.68386(16) 0.2481(2) 0.41854(7) 0.0397(3) Uani 1 1 d . . .
O3 O 0.78702(18) 0.9924(4) 0.00890(8) 0.0625(5) Uani 1 1 d . . .
C2 C 0.8580(2) 1.0110(3) 0.15288(10) 0.0385(4) Uani 1 1 d . . .
O6 O 0.96311(18) 0.4337(3) 0.36954(9) 0.0510(4) Uani 1 1 d . . .
N6 N 0.51126(18) 0.3583(2) 0.32744(8) 0.0330(3) Uani 1 1 d . . .
C12 C 0.5345(2) 0.3185(3) 0.40588(10) 0.0362(4) Uani 1 1 d . . .
C19 C 0.6319(2) 0.3815(3) 0.28356(10) 0.0329(4) Uani 1 1 d . . .
H19 H 0.7322 0.3736 0.3030 0.040 Uiso 1 1 calc R . .
C17 C 0.4534(2) 0.4264(3) 0.18542(11) 0.0392(5) Uani 1 1 d . . .
N1 N 0.6135(2) 0.9335(4) 0.25719(12) 0.0610(6) Uani 1 1 d . . .
N8 N 0.4252(3) 0.4592(4) 0.11591(11) 0.0563(6) Uani 1 1 d . . .
O2 O 1.0205(3) 0.8258(3) 0.37830(10) 0.0654(5) Uani 1 1 d . . .
N2 N 0.5350(2) 0.8894(3) 0.30447(13) 0.0583(6) Uani 1 1 d . . .
C8 C 1.1923(3) 0.9736(4) -0.00801(11) 0.0445(5) Uani 1 1 d . . .
C10 C 1.1306(2) 0.9961(4) 0.11594(11) 0.0465(5) Uani 1 1 d . . .
H10 H 1.1606 1.0004 0.1648 0.056 Uiso 1 1 calc R . .
C18 C 0.6079(2) 0.4154(3) 0.21351(11) 0.0359(4) Uani 1 1 d . . .
H18 H 0.6901 0.4314 0.1836 0.043 Uiso 1 1 calc R . .
C7 C 0.9229(3) 0.9945(4) 0.02674(11) 0.0436(5) Uani 1 1 d . . .
C13 C 0.5135(2) 0.4887(4) 0.45148(12) 0.0454(5) Uani 1 1 d . . .
H13A H 0.4851 0.4560 0.5000 0.054 Uiso 1 1 calc R . .
H13B H 0.4350 0.5689 0.4298 0.054 Uiso 1 1 calc R . .
C9 C 1.2412(2) 0.9813(4) 0.06787(11) 0.0459(5) Uani 1 1 d . . .
C3 C 0.8051(3) 0.8217(3) 0.17587(11) 0.0447(5) Uani 1 1 d . . .
H3A H 0.8854 0.7304 0.1707 0.054 Uiso 1 1 calc R . .
H3B H 0.7136 0.7834 0.1479 0.054 Uiso 1 1 calc R . .
C4 C 0.7710(2) 0.8506(3) 0.25465(11) 0.0415(5) Uani 1 1 d . . .
C11 C 1.4099(3) 0.9715(6) 0.08698(14) 0.0686(8) Uani 1 1 d . . .
H11A H 1.4260 0.9735 0.1386 0.103 Uiso 1 1 calc R . .
H11B H 1.4608 1.0752 0.0664 0.103 Uiso 1 1 calc R . .
H11C H 1.4513 0.8594 0.0682 0.103 Uiso 1 1 calc R . .
C15 C 0.9469(3) 0.3554(4) 0.43921(12) 0.0491(5) Uani 1 1 d . . .
H15A H 1.0141 0.4194 0.4741 0.059 Uiso 1 1 calc R . .
H15B H 0.9778 0.2269 0.4385 0.059 Uiso 1 1 calc R . .
C14 C 0.7833(2) 0.3689(4) 0.46181(11) 0.0435(5) Uani 1 1 d . . .
C6 C 1.0409(3) 0.9004(4) 0.30910(12) 0.0489(6) Uani 1 1 d . . .
H6A H 1.0717 0.8034 0.2766 0.059 Uiso 1 1 calc R . .
H6B H 1.1222 0.9921 0.3120 0.059 Uiso 1 1 calc R . .
C5 C 0.8935(3) 0.9884(3) 0.27955(10) 0.0398(5) Uani 1 1 d . . .
N3 N 0.4524(4) 0.8672(6) 0.3490(2) 0.1189(14) Uani 1 1 d . . .
O8 O 0.0384(2) 0.4534(3) 0.17309(9) 0.0480(4) Uani 1 1 d . . .
H2 H 0.776(2) 1.088(3) 0.1302(11) 0.036(5) Uiso 1 1 d . . .
H4 H 0.777(2) 0.746(4) 0.2814(12) 0.035(5) Uiso 1 1 d . . .
H5 H 0.860(2) 1.067(3) 0.3121(11) 0.031(5) Uiso 1 1 d . . .
H12 H 0.461(2) 0.224(3) 0.4180(11) 0.026(5) Uiso 1 1 d . . .
H14 H 0.781(3) 0.319(3) 0.5141(13) 0.043(6) Uiso 1 1 d . . .
H5N H 1.006(3) 0.980(4) -0.0675(14) 0.047(7) Uiso 1 1 d . . .
H8NA H 0.502(4) 0.473(4) 0.0905(14) 0.058(8) Uiso 1 1 d . . .
H8NB H 0.335(4) 0.474(4) 0.1006(15) 0.057(8) Uiso 1 1 d . . .
H2O H 0.984(6) 0.711(9) 0.380(3) 0.15(2) Uiso 1 1 d . . .
H6O H 1.049(4) 0.405(5) 0.3591(17) 0.074(10) Uiso 1 1 d . . .
H8OA H 0.124(4) 0.432(4) 0.1914(14) 0.051(7) Uiso 1 1 d . . .
H8OB H 0.005(4) 0.389(5) 0.1986(18) 0.066(10) Uiso 1 1 d . . .
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 0.0000 0.0000 '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 0.0060 '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_
_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
C13 S1 C14 87.38(11) . . ?
C10 N4 C7 121.10(17) . . ?
C10 N4 C2 122.20(15) . . ?
C7 N4 C2 116.50(16) . . ?
C2 O1 C5 110.43(16) . . ?
C8 N5 C7 127.36(17) . . ?
C8 N5 H5N 116.3(16) . . ?
C7 N5 H5N 116.4(16) . . ?
O7 C16 N7 123.00(18) . . ?
O7 C16 N6 117.86(18) . . ?
N7 C16 N6 119.13(17) . . ?
C17 N7 C16 120.25(17) . . ?
C12 O5 C14 113.38(16) . . ?
O1 C2 N4 108.27(16) . . ?
O1 C2 C3 106.42(16) . . ?
N4 C2 C3 113.37(18) . . ?
O1 C2 H2 110.9(13) . . ?
N4 C2 H2 103.4(12) . . ?
C3 C2 H2 114.4(13) . . ?
C15 O6 H6O 104(2) . . ?
C19 N6 C16 120.42(16) . . ?
C19 N6 C12 122.05(15) . . ?
C16 N6 C12 117.53(15) . . ?
O5 C12 N6 108.58(15) . . ?
O5 C12 C13 109.71(17) . . ?
N6 C12 C13 111.90(18) . . ?
O5 C12 H12 108.6(12) . . ?
N6 C12 H12 107.4(12) . . ?
C13 C12 H12 110.5(12) . . ?
C18 C19 N6 120.82(17) . . ?
C18 C19 H19 119.6 . . ?
N6 C19 H19 119.6 . . ?
N8 C17 N7 118.98(19) . . ?
N8 C17 C18 119.89(19) . . ?
N7 C17 C18 121.13(18) . . ?
N2 N1 C4 118.3(2) . . ?
C17 N8 H8NA 116.5(18) . . ?
C17 N8 H8NB 119.1(19) . . ?
H8NA N8 H8NB 124(3) . . ?
C6 O2 H2O 117(3) . . ?
N3 N2 N1 171.9(3) . . ?
O4 C8 N5 119.65(19) . . ?
O4 C8 C9 124.8(2) . . ?
N5 C8 C9 115.56(18) . . ?
C9 C10 N4 124.24(18) . . ?
C9 C10 H10 117.9 . . ?
N4 C10 H10 117.9 . . ?
C19 C18 C17 118.26(17) . . ?
C19 C18 H18 120.9 . . ?
C17 C18 H18 120.9 . . ?
O3 C7 N5 122.60(18) . . ?
O3 C7 N4 122.92(19) . . ?
N5 C7 N4 114.48(18) . . ?
C12 C13 S1 103.66(14) . . ?
C12 C13 H13A 111.0 . . ?
S1 C13 H13A 111.0 . . ?
C12 C13 H13B 111.0 . . ?
S1 C13 H13B 111.0 . . ?
H13A C13 H13B 109.0 . . ?
C10 C9 C8 117.19(19) . . ?
C10 C9 C11 124.8(2) . . ?
C8 C9 C11 118.0(2) . . ?
C2 C3 C4 102.68(18) . . ?
C2 C3 H3A 111.2 . . ?
C4 C3 H3A 111.2 . . ?
C2 C3 H3B 111.2 . . ?
C4 C3 H3B 111.2 . . ?
H3A C3 H3B 109.1 . . ?
N1 C4 C3 107.65(19) . . ?
N1 C4 C5 110.9(2) . . ?
C3 C4 C5 102.66(17) . . ?
N1 C4 H4 110.7(14) . . ?
C3 C4 H4 113.5(15) . . ?
C5 C4 H4 111.2(14) . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O6 C15 C14 111.04(18) . . ?
O6 C15 H15A 109.4 . . ?
C14 C15 H15A 109.4 . . ?
O6 C15 H15B 109.4 . . ?
C14 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
O5 C14 C15 110.84(19) . . ?
O5 C14 S1 106.11(14) . . ?
C15 C14 S1 114.36(19) . . ?
O5 C14 H14 105.6(14) . . ?
C15 C14 H14 107.2(13) . . ?
S1 C14 H14 112.4(14) . . ?
O2 C6 C5 110.6(2) . . ?
O2 C6 H6A 109.5 . . ?
C5 C6 H6A 109.5 . . ?
O2 C6 H6B 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 108.1 . . ?
O1 C5 C6 110.02(17) . . ?
O1 C5 C4 105.08(16) . . ?
C6 C5 C4 113.9(2) . . ?
O1 C5 H5 106.4(13) . . ?
C6 C5 H5 108.7(13) . . ?
C4 C5 H5 112.5(13) . . ?
H8OA O8 H8OB 89(3) . . ?
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
S1 C13 1.803(2) . ?
S1 C14 1.815(3) . ?
N4 C10 1.371(3) . ?
N4 C7 1.376(2) . ?
N4 C2 1.479(2) . ?
O1 C2 1.420(2) . ?
O1 C5 1.449(2) . ?
N5 C8 1.370(3) . ?
N5 C7 1.374(3) . ?
N5 H5N 0.86(3) . ?
O4 C8 1.218(3) . ?
O7 C16 1.237(3) . ?
C16 N7 1.350(3) . ?
C16 N6 1.391(3) . ?
N7 C17 1.334(3) . ?
O5 C12 1.405(2) . ?
O5 C14 1.447(3) . ?
O3 C7 1.212(3) . ?
C2 C3 1.514(3) . ?
C2 H2 0.99(2) . ?
O6 C15 1.421(3) . ?
O6 H6O 0.81(3) . ?
N6 C19 1.364(2) . ?
N6 C12 1.485(2) . ?
C12 C13 1.510(3) . ?
C12 H12 0.97(2) . ?
C19 C18 1.327(3) . ?
C19 H19 0.9300 . ?
C17 N8 1.320(3) . ?
C17 C18 1.421(3) . ?
N1 N2 1.177(3) . ?
N1 C4 1.497(3) . ?
N8 H8NA 0.84(3) . ?
N8 H8NB 0.83(3) . ?
O2 C6 1.408(3) . ?
O2 H2O 0.89(6) . ?
N2 N3 1.127(4) . ?
C8 C9 1.450(3) . ?
C10 C9 1.342(3) . ?
C10 H10 0.9300 . ?
C18 H18 0.9300 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C9 C11 1.495(3) . ?
C3 C4 1.515(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.517(3) . ?
C4 H4 0.91(3) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C15 C14 1.503(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C14 H14 1.03(2) . ?
C6 C5 1.512(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C5 H5 0.89(2) . ?
O8 H8OA 0.82(3) . ?
O8 H8OB 0.73(4) . ?
