##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
{(1S,4R)-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-
yl]cyclopent-2-en-1-yl}methanol methanol 2.5-solvate
;
_chemical_name_common     'abacavir methanol 2.5-solvate'
_chemical_formula_moiety     'C14 H18 N6 O, 2.5(C1 H4 O1)'
_chemical_formula_sum     'C16.50 H28 N6 O3.50'
_chemical_formula_iupac     'C14 H18 N6 O, 2.5C1 H4 O1'
_chemical_formula_weight     366.45
_chemical_melting_point     ?
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     'C 2'
_symmetry_space_group_name_Hall     'C 2y'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y, -z'
    'x+1/2, y+1/2, z'
    '-x+1/2, y+1/2, -z'
_cell_length_a     19.857(4)
_cell_length_b     7.2552(15)
_cell_length_c     13.735(3)
_cell_angle_alpha     90.00
_cell_angle_beta     98.27(3)
_cell_angle_gamma     90.00
_cell_volume     1958.2(7)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     2936
_cell_measurement_theta_min     2.38
_cell_measurement_theta_max     27.43
_cell_measurement_temperature     173(2)
_exptl_crystal_description     rod
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.60
_exptl_crystal_size_mid     0.30
_exptl_crystal_size_min     0.15
_exptl_crystal_density_diffrn     1.243
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     788
_exptl_absorpt_coefficient_mu     0.090
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     '(SADABS; Bruker, 2003)'
_exptl_absorpt_correction_T_min     0.9482
_exptl_absorpt_correction_T_max     0.9867
_exptl_special_details
;
?
;
_diffrn_ambient_temperature     173(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'normal-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART Platform CCD'
_diffrn_measurement_method     'area detector, ω scans per φ'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     10335
_diffrn_reflns_av_R_equivalents     0.024
_diffrn_reflns_av_sigmaI/netI     0.021
_diffrn_reflns_theta_min     1.50
_diffrn_reflns_theta_max     27.5
_diffrn_reflns_theta_full     27.5
_diffrn_measured_fraction_theta_max     0.988
_diffrn_measured_fraction_theta_full     0.988
_diffrn_reflns_limit_h_min     -25
_diffrn_reflns_limit_h_max     25
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -17
_diffrn_reflns_limit_l_max     17
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_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 > 2sigma(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.
;
_reflns_number_total     2405
_reflns_number_gt     2231
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.039
_refine_ls_R_factor_gt     0.036
_refine_ls_wR_factor_gt     0.097
_refine_ls_wR_factor_ref     0.099
_refine_ls_goodness_of_fit_ref     1.014
_refine_ls_restrained_S_all     1.014
_refine_ls_number_reflns     2405
_refine_ls_number_parameters     190
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0623P)²+0.4691P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.18
_refine_diff_density_min     -0.19
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_details     ?
_refine_ls_abs_structure_Flack     ?
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 0.0000
                         '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 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'SMART (Bruker, 2003)'
_computing_cell_refinement     'SAINT (Bruker, 2006)'
_computing_data_reduction     'SAINT (Bruker, 2006)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material     'SHELXTL (Sheldrick, 2008)'
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    O O1 0.78278(7) 0.9453(2) 0.79352(11) 0.0435(4) Uani d . 1 . .
    H H1O 0.8119 1.0020 0.7664 0.065 Uiso d R 1 . .
    N N1 0.41393(7) 0.5553(3) 0.92222(10) 0.0353(4) Uani d . 1 . .
    H H1A 0.4354 0.5494 0.9828 0.042 Uiso d R 1 . .
    H H1B 0.3694 0.5669 0.9115 0.042 Uiso d R 1 . .
    N N2 0.41135(7) 0.5588(2) 0.75419(9) 0.0265(3) Uani d . 1 . .
    N N3 0.40604(7) 0.5727(2) 0.58458(9) 0.0302(4) Uani d . 1 . .
    H H3N 0.4273 0.5824 0.5328 0.036 Uiso d R 1 . .
    N N4 0.51700(7) 0.5290(2) 0.86615(9) 0.0252(3) Uani d . 1 . .
    N N5 0.56198(7) 0.5232(3) 0.62195(9) 0.0307(3) Uani d . 1 . .
    N N6 0.61422(7) 0.4984(2) 0.77840(9) 0.0259(3) Uani d . 1 . .
    C C1 0.44957(8) 0.5466(3) 0.84530(11) 0.0253(3) Uani d . 1 . .
    C C2 0.44332(8) 0.5568(3) 0.67411(11) 0.0253(3) Uani d . 1 . .
    C C3 0.33305(10) 0.5746(4) 0.57052(13) 0.0413(5) Uani d . 1 . .
    H H3 0.3100 0.4545 0.5796 0.050 Uiso calc R 1 . .
    C C4 0.29783(13) 0.7005(5) 0.49353(15) 0.0589(8) Uani d . 1 . .
    H H4A 0.2545 0.6579 0.4555 0.071 Uiso calc R 1 . .
    H H4B 0.3265 0.7770 0.4560 0.071 Uiso calc R 1 . .
    C C5 0.29839(14) 0.7448(5) 0.60113(15) 0.0671(9) Uani d . 1 . .
    H H5B 0.3274 0.8480 0.6294 0.080 Uiso calc R 1 . .
    H H5C 0.2554 0.7290 0.6289 0.080 Uiso calc R 1 . .
    C C6 0.51484(8) 0.5376(3) 0.68753(11) 0.0249(3) Uani d . 1 . .
    C C7 0.54633(8) 0.5233(2) 0.78383(11) 0.0234(3) Uani d . 1 . .
    C C8 0.61989(8) 0.5003(3) 0.67988(11) 0.0295(4) Uani d . 1 . .
    H H8 0.6621 0.4863 0.6558 0.035 Uiso calc R 1 . .
    C C9 0.66820(9) 0.4790(3) 0.86407(11) 0.0295(4) Uani d . 1 . .
    H H9 0.6478 0.4289 0.9210 0.035 Uiso calc R 1 . .
    C C10 0.70507(9) 0.6626(3) 0.89483(14) 0.0346(4) Uani d . 1 . .
    H H10A 0.7068 0.6837 0.9664 0.042 Uiso calc R 1 . .
    H H10B 0.6811 0.7675 0.8590 0.042 Uiso calc R 1 . .
    C C11 0.77807(9) 0.6425(3) 0.86777(13) 0.0314(4) Uani d . 1 . .
    H H11 0.8127 0.6785 0.9248 0.038 Uiso calc R 1 . .
    C C12 0.78314(10) 0.4411(3) 0.84697(14) 0.0349(4) Uani d . 1 . .
    H H12 0.8245 0.3822 0.8380 0.042 Uiso calc R 1 . .
    C C13 0.72425(9) 0.3522(3) 0.84218(13) 0.0322(4) Uani d . 1 . .
    H H13 0.7182 0.2250 0.8269 0.039 Uiso calc R 1 . .
    C C14 0.78838(11) 0.7532(3) 0.77666(15) 0.0398(5) Uani d . 1 . .
    H H14A 0.8339 0.7260 0.7589 0.048 Uiso calc R 1 . .
    H H14B 0.7539 0.7160 0.7208 0.048 Uiso calc R 1 . .
_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_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    O1 C14 . 1.419(3) ?
    O1 H1O . 0.8394 ?
    N1 C1 . 1.355(2) ?
    N1 H1A . 0.8798 ?
    N1 H1B . 0.8801 ?
    N2 C2 . 1.347(2) ?
    N2 C1 . 1.370(2) ?
    N3 C2 . 1.346(2) ?
    N3 C3 . 1.434(2) ?
    N3 H3N . 0.8804 ?
    N4 C1 . 1.334(2) ?
    N4 C7 . 1.345(2) ?
    N5 C8 . 1.311(2) ?
    N5 C6 . 1.393(2) ?
    N6 C7 . 1.373(2) ?
    N6 C8 . 1.374(2) ?
    N6 C9 . 1.480(2) ?
    C2 C6 . 1.412(2) ?
    C3 C4 . 1.493(3) ?
    C3 C5 . 1.503(4) ?
    C3 H3 . 1.0000 ?
    C4 C5 . 1.511(3) ?
    C4 H4A . 0.9900 ?
    C4 H4B . 0.9900 ?
    C5 H5B . 0.9900 ?
    C5 H5C . 0.9900 ?
    C6 C7 . 1.383(2) ?
    C8 H8 . 0.9500 ?
    C9 C13 . 1.507(3) ?
    C9 C10 . 1.550(3) ?
    C9 H9 . 1.0000 ?
    C10 C11 . 1.554(2) ?
    C10 H10A . 0.9900 ?
    C10 H10B . 0.9900 ?
    C11 C12 . 1.495(3) ?
    C11 C14 . 1.526(3) ?
    C11 H11 . 1.0000 ?
    C12 C13 . 1.329(3) ?
    C12 H12 . 0.9500 ?
    C13 H13 . 0.9500 ?
    C14 H14A . 0.9900 ?
    C14 H14B . 0.9900 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C14 O1 H1O . . 109.5 ?
    C1 N1 H1A . . 120.0 ?
    C1 N1 H1B . . 120.0 ?
    H1A N1 H1B . . 120.0 ?
    C2 N2 C1 . . 118.76(13) ?
    C2 N3 C3 . . 122.41(14) ?
    C2 N3 H3N . . 118.8 ?
    C3 N3 H3N . . 118.8 ?
    C1 N4 C7 . . 111.41(13) ?
    C8 N5 C6 . . 103.26(13) ?
    C7 N6 C8 . . 105.80(13) ?
    C7 N6 C9 . . 125.03(13) ?
    C8 N6 C9 . . 129.15(14) ?
    N4 C1 N1 . . 117.23(14) ?
    N4 C1 N2 . . 127.52(14) ?
    N1 C1 N2 . . 115.24(14) ?
    N3 C2 N2 . . 118.91(15) ?
    N3 C2 C6 . . 122.56(14) ?
    N2 C2 C6 . . 118.54(14) ?
    N3 C3 C4 . . 117.6(2) ?
    N3 C3 C5 . . 117.7(2) ?
    C4 C3 C5 . . 60.57(16) ?
    N3 C3 H3 . . 116.5 ?
    C4 C3 H3 . . 116.5 ?
    C5 C3 H3 . . 116.5 ?
    C3 C4 C5 . . 60.04(16) ?
    C3 C4 H4A . . 117.8 ?
    C5 C4 H4A . . 117.8 ?
    C3 C4 H4B . . 117.8 ?
    C5 C4 H4B . . 117.8 ?
    H4A C4 H4B . . 114.9 ?
    C3 C5 C4 . . 59.39(16) ?
    C3 C5 H5B . . 117.8 ?
    C4 C5 H5B . . 117.8 ?
    C3 C5 H5C . . 117.8 ?
    C4 C5 H5C . . 117.8 ?
    H5B C5 H5C . . 115.0 ?
    C7 C6 N5 . . 111.05(14) ?
    C7 C6 C2 . . 116.10(14) ?
    N5 C6 C2 . . 132.81(14) ?
    N4 C7 N6 . . 126.66(14) ?
    N4 C7 C6 . . 127.64(14) ?
    N6 C7 C6 . . 105.69(14) ?
    N5 C8 N6 . . 114.20(14) ?
    N5 C8 H8 . . 122.9 ?
    N6 C8 H8 . . 122.9 ?
    N6 C9 C13 . . 111.75(14) ?
    N6 C9 C10 . . 113.26(16) ?
    C13 C9 C10 . . 104.22(15) ?
    N6 C9 H9 . . 109.2 ?
    C13 C9 H9 . . 109.2 ?
    C10 C9 H9 . . 109.2 ?
    C9 C10 C11 . . 105.93(16) ?
    C9 C10 H10A . . 110.5 ?
    C11 C10 H10A . . 110.5 ?
    C9 C10 H10B . . 110.5 ?
    C11 C10 H10B . . 110.5 ?
    H10A C10 H10B . . 108.7 ?
    C12 C11 C14 . . 109.71(16) ?
    C12 C11 C10 . . 103.19(17) ?
    C14 C11 C10 . . 112.74(16) ?
    C12 C11 H11 . . 110.3 ?
    C14 C11 H11 . . 110.3 ?
    C10 C11 H11 . . 110.3 ?
    C13 C12 C11 . . 113.64(19) ?
    C13 C12 H12 . . 123.2 ?
    C11 C12 H12 . . 123.2 ?
    C12 C13 C9 . . 111.33(19) ?
    C12 C13 H13 . . 124.3 ?
    C9 C13 H13 . . 124.3 ?
    O1 C14 C11 . . 111.11(17) ?
    O1 C14 H14A . . 109.4 ?
    C11 C14 H14A . . 109.4 ?
    O1 C14 H14B . . 109.4 ?
    C11 C14 H14B . . 109.4 ?
    H14A C14 H14B . . 108.0 ?
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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C7 N4 C1 N1 . . . . -179.56(17) ?
    C7 N4 C1 N2 . . . . -0.2(3) ?
    C2 N2 C1 N4 . . . . -1.3(3) ?
    C2 N2 C1 N1 . . . . 178.04(17) ?
    C3 N3 C2 N2 . . . . -5.9(3) ?
    C3 N3 C2 C6 . . . . 174.0(2) ?
    C1 N2 C2 N3 . . . . -178.59(17) ?
    C1 N2 C2 C6 . . . . 1.5(3) ?
    C2 N3 C3 C4 . . . . 142.2(2) ?
    C2 N3 C3 C5 . . . . 72.8(3) ?
    N3 C3 C4 C5 . . . . -107.9(3) ?
    N3 C3 C5 C4 . . . . 107.7(2) ?
    C8 N5 C6 C7 . . . . 0.2(2) ?
    C8 N5 C6 C2 . . . . -177.3(2) ?
    N3 C2 C6 C7 . . . . 179.77(18) ?
    N2 C2 C6 C7 . . . . -0.4(3) ?
    N3 C2 C6 N5 . . . . -2.9(3) ?
    N2 C2 C6 N5 . . . . 177.0(2) ?
    C1 N4 C7 N6 . . . . -177.05(18) ?
    C1 N4 C7 C6 . . . . 1.6(3) ?
    C8 N6 C7 N4 . . . . 179.31(18) ?
    C9 N6 C7 N4 . . . . -2.1(3) ?
    C8 N6 C7 C6 . . . . 0.4(2) ?
    C9 N6 C7 C6 . . . . 179.02(18) ?
    N5 C6 C7 N4 . . . . -179.26(18) ?
    C2 C6 C7 N4 . . . . -1.3(3) ?
    N5 C6 C7 N6 . . . . -0.4(2) ?
    C2 C6 C7 N6 . . . . 177.52(17) ?
    C6 N5 C8 N6 . . . . 0.1(2) ?
    C7 N6 C8 N5 . . . . -0.4(2) ?
    C9 N6 C8 N5 . . . . -178.85(19) ?
    C7 N6 C9 C13 . . . . 146.99(18) ?
    C8 N6 C9 C13 . . . . -34.8(3) ?
    C7 N6 C9 C10 . . . . -95.7(2) ?
    C8 N6 C9 C10 . . . . 82.6(2) ?
    N6 C9 C10 C11 . . . . -110.14(16) ?
    C13 C9 C10 C11 . . . . 11.53(19) ?
    C9 C10 C11 C12 . . . . -12.79(19) ?
    C9 C10 C11 C14 . . . . 105.50(19) ?
    C14 C11 C12 C13 . . . . -110.41(19) ?
    C10 C11 C12 C13 . . . . 10.0(2) ?
    C11 C12 C13 C9 . . . . -2.7(2) ?
    N6 C9 C13 C12 . . . . 116.80(18) ?
    C10 C9 C13 C12 . . . . -5.9(2) ?
    C12 C11 C14 O1 . . . . 179.07(17) ?
    C10 C11 C14 O1 . . . . 64.7(2) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    N1 H1A N4 2_657 0.88 2.16 3.036(2) 176.9
    N1 H1B O1 3_445 0.88 2.36 3.036(2) 134.0
    N3 H3N N5 2_656 0.88 2.21 3.016(2) 152.4
    O1 H1O N2 3 0.84 2.05 2.808(2) 150.4
data_global
_journal_date_recd_electronic     2009-07-08
_journal_date_accepted     2009-07-14
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2009
_journal_volume     65
_journal_issue      8
_journal_page_first     o1937
_journal_page_last     o1937
_journal_paper_category     QO
_journal_coeditor_code     PV2180
_publ_contact_author_name     'Professor Phuong-Truc T. Pham'
_publ_contact_author_address
;
Department of Chemistry
Penn State Worthington Scranton
120 Ridge View Drive
Dumore, Pennsylvania 18512
USA
;
_publ_contact_author_email     ptp2@psu.edu
_publ_contact_author_fax     '570 963 2535'
_publ_contact_author_phone     '570 963 2564'
_publ_section_title
;
Abacavir methanol 2.5-solvate
;
loop_
    _publ_author_name
    _publ_author_address
    'Pham, Phuong-Truc T.'
;
Department of Chemistry
Penn State Worthington Scranton
120 Ridge View Drive
Dunmore, Pennsylvania 18512
USA
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