#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/28/2222848.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2222848
loop_
_publ_author_name
'Pham, Phuong-Truc T.'
_publ_section_title
;
 Abacavir methanol 2.5-solvate
;
_journal_coeditor_code           PV2180
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1937
_journal_paper_doi               10.1107/S1600536809027743
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C14 H18 N6 O, 2.5C1 H4 O1'
_chemical_formula_moiety         'C14 H18 N6 O, 2.5(C1 H4 O1)'
_chemical_formula_sum            'C16.5 H28 N6 O3.5'
_chemical_formula_weight         366.45
_chemical_name_common            'abacavir methanol 2.5-solvate'
_chemical_name_systematic
;
{(1S,4R)-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-
yl]cyclopent-2-en-1-yl}methanol methanol 2.5-solvate
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 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                 98.27(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.857(4)
_cell_length_b                   7.2552(15)
_cell_length_c                   13.735(3)
_cell_measurement_reflns_used    2936
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.43
_cell_measurement_theta_min      2.38
_cell_volume                     1958.2(7)
_computing_cell_refinement       'SAINT (Bruker, 2006)'
_computing_data_collection       'SMART (Bruker, 2003)'
_computing_data_reduction        'SAINT (Bruker, 2006)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker SMART Platform CCD'
_diffrn_measurement_method       'area detector, ω scans per φ'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.024
_diffrn_reflns_av_sigmaI/netI    0.021
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10335
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         1.50
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.9867
_exptl_absorpt_correction_T_min  0.9482
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2003)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             788
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.18
_refine_diff_density_min         -0.19
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2405
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.039
_refine_ls_R_factor_gt           0.036
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0623P)²+0.4691P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.097
_refine_ls_wR_factor_ref         0.099
_reflns_number_gt                2231
_reflns_number_total             2405
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            pv2180.cif
_cod_data_source_block           I
_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 

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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'C 2'
_cod_original_formula_sum        'C16.50 H28 N6 O3.50'
_cod_database_code               2222848
_cod_database_fobs_code          2222848
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'
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 . .
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'
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_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_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
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_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 390063
