data_2008574
_journal_name_full  'Acta Crystallographica'
_journal_year  1999
_journal_volume  C55
_journal_page_first  1005
_journal_page_last  1008
_publ_section_title
;
(2S,3S)- and (2R,3S)-2-[2-(benzyloxy)ethyl]-3-(6-chloro-9H-purin-9-yl)oxolane
;
loop_
_publ_author_name
  'George Balayiannis'
  'Ioannis Argiris'
  'Dionissios Papaioannou'
  'Constantin Kavounis'
_chemical_formula_moiety  'C18 H19 Cl N4 O2'
_chemical_formula_sum  'C18 H19 Cl N4 O2'
_chemical_formula_weight  358.82
_symmetry_cell_setting  orthorhombic
_symmetry_space_group_name_H-M  'C 2 2 21'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, -y, z+1/2'
  '-x, y, -z+1/2'
  'x, -y, -z'
  'x+1/2, y+1/2, z'
  '-x+1/2, -y+1/2, z+1/2'
  '-x+1/2, y+1/2, -z+1/2'
  'x+1/2, -y+1/2, -z'
_cell_length_a  7.7541(13)
_cell_length_b  14.4655(19)
_cell_length_c  31.108(5)
_cell_angle_alpha  90.00
_cell_angle_beta  90.00
_cell_angle_gamma  90.00
_cell_volume  3489.3(10)
_cell_formula_units_Z  8
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.366
_diffrn_ambient_temperature  293(2)
loop_
_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
_atom_site_type_symbol
  Cl1  .11312(13)  .62634(7)  .31906(3)  .0698(3) Uani d . 1 . . Cl
  N1  .2338(4)  .73361(17)  .25863(9)  .0591(7) Uani d . 1 . . N
  C2  .3097(5)  .7487(2)  .22079(12)  .0664(9) Uani d . 1 . . C
  H2  .3261  .8104  .2134  .080 Uiso calc R 1 . . H
  N3  .3654(4)  .68652(16)  .19203(8)  .0543(6) Uani d . 1 . . N
  C4  .3381(4)  .60073(18)  .20532(8)  .0423(6) Uani d . 1 . . C
  C5  .2600(4)  .57453(17)  .24404(9)  .0432(6) Uani d . 1 . . C
  C6  .2100(4)  .6470(2)  .26988(9)  .0506(7) Uani d . 1 . . C
  N7  .2526(4)  .47982(14)  .24742(9)  .0520(6) Uani d . 1 . . N
  C8  .3245(5)  .45133(19)  .21171(9)  .0528(7) Uani d . 1 . . C
  H8  .3369  .3890  .2050  .063 Uiso calc R 1 . . H
  N9  .3797(3)  .51988(14)  .18506(6)  .0431(5) Uani d . 1 . . N
  C10  .4701(4)  .51306(18)  .14361(8)  .0441(6) Uani d . 1 . . C
  H10  .5220  .5729  .1365  .053 Uiso calc R 1 . . H
  C11  .6093(4)  .4384(2)  .14351(10)  .0562(7) Uani d . 1 . . C
  H11A  .7104  .4588  .1278  .067 Uiso calc R 1 . . H
  H11B  .6431  .4225  .1726  .067 Uiso calc R 1 . . H
  C12  .5251(5)  .3571(2)  .12142(13)  .0671(9) Uani d . 1 . . C
  H12A  .5893  .3404  .0958  .081 Uiso calc R 1 . . H
  H12B  .5224  .3041  .1405  .081 Uiso calc R 1 . . H
  O13  .3543(3)  .38413(14)  .11028(7)  .0583(5) Uani d . 1 . . O
  C14  .3543(4)  .4824(2)  .10720(8)  .0472(6) Uani d . 1 . . C
  H14  .4087  .4999  .0800  .057 Uiso calc R 1 . . H
  C15  .1701(4)  .5168(2)  .10687(9)  .0530(7) Uani d . 1 . . C
  H15A  .1094  .4914  .1314  .064 Uiso calc R 1 . . H
  H15B  .1701  .5836  .1097  .064 Uiso calc R 1 . . H
  C16  .0765(4)  .4906(3)  .06653(10)  .0611(8) Uani d . 1 . . C
  H16A  .1399  .5141  .0420  .073 Uiso calc R 1 . . H
  H16B  .0733  .4237  .0643  .073 Uiso calc R 1 . . H
  O17  -.0966(3)  .52568(16)  .06516(8)  .0646(6) Uani d . 1 . . O
  C18  -.1067(5)  .6156(3)  .04922(17)  .0843(13) Uani d . 1 . . C
  H18A  -.0505  .6187  .0214  .101 Uiso calc R 1 . . H
  H18B  -.0477  .6575  .0686  .101 Uiso calc R 1 . . H
  C19  -.2930(4)  .6443(2)  .04481(11)  .0546(7) Uani d . 1 . . C
  C20  -.3667(5)  .6972(2)  .07644(11)  .0653(9) Uani d . 1 . . C
  H20  -.3023  .7141  .1004  .078 Uiso calc R 1 . . H
  C21  -.5373(6)  .7256(2)  .07278(14)  .0733(10) Uani d . 1 . . C
  H21  -.5885  .7599  .0946  .088 Uiso calc R 1 . . H
  C22  -.6289(5)  .7027(3)  .03698(14)  .0764(11) Uani d . 1 . . C
  H22  -.7424  .7227  .0342  .092 Uiso calc R 1 . . H
  C23  -.5563(5)  .6510(3)  .00535(13)  .0720(10) Uani d . 1 . . C
  H23  -.6202  .6355  -.0189  .086 Uiso calc R 1 . . H
  C24  -.3874(5)  .6214(2)  .00911(11)  .0633(8) Uani d . 1 . . C
  H24  -.3379  .5860  -.0126  .076 Uiso calc R 1 . . H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
  Cl1  .0685(5)  .0889(6)  .0521(4)  .0133(5)  .0055(4)  -.0113(4)
  N1  .0674(17)  .0479(13)  .0619(16)  .0104(13)  -.0047(14)  -.0092(11)
  C2  .081(2)  .0380(14)  .081(2)  .0037(16)  -.009(2)  -.0001(14)
  N3  .0630(16)  .0377(11)  .0622(14)  -.0008(12)  -.0008(13)  .0015(10)
  C4  .0429(14)  .0403(12)  .0439(12)  .0012(11)  -.0057(11)  .0004(10)
  C5  .0423(13)  .0451(12)  .0423(13)  .0023(11)  -.0050(11)  -.0013(11)
  C6  .0442(15)  .0600(17)  .0475(14)  .0080(13)  -.0075(12)  -.0102(12)
  N7  .0661(15)  .0448(11)  .0452(11)  -.0016(12)  .0040(11)  .0038(11)
  C8  .070(2)  .0402(13)  .0479(14)  -.0024(14)  .0001(15)  .0023(11)
  N9  .0504(12)  .0374(10)  .0415(10)  -.0012(10)  -.0018(11)  .0005(8)
  C10  .0442(14)  .0421(13)  .0462(13)  -.0013(12)  .0022(11)  .0026(11)
  C11  .0445(15)  .0656(18)  .0583(16)  .0069(15)  -.0004(14)  -.0055(13)
  C12  .069(2)  .0523(17)  .080(2)  .0146(17)  -.0038(18)  -.0070(15)
  O13  .0548(12)  .0489(11)  .0712(13)  -.0028(10)  -.0074(11)  -.0082(10)
  C14  .0478(15)  .0509(15)  .0428(12)  .0032(13)  .0024(12)  .0006(11)
  C15  .0472(15)  .0621(17)  .0496(15)  .0065(14)  -.0001(12)  .0007(13)
  C16  .0480(16)  .073(2)  .0625(18)  .0073(16)  -.0061(14)  .0033(16)
  O17  .0442(11)  .0716(15)  .0780(14)  .0043(11)  -.0056(11)  .0211(12)
  C18  .0433(17)  .083(3)  .127(3)  -.0032(19)  -.001(2)  .046(2)
  C19  .0430(15)  .0502(15)  .0705(18)  -.0053(13)  -.0013(14)  .0219(15)
  C20  .072(2)  .0595(19)  .0641(18)  -.0152(18)  -.0120(18)  .0088(15)
  C21  .080(3)  .0516(18)  .089(3)  .0074(19)  .018(2)  .0067(18)
  C22  .0447(18)  .070(2)  .114(3)  .0039(17)  -.004(2)  .038(2)
  C23  .063(2)  .080(2)  .073(2)  -.0176(19)  -.0196(19)  .0179(19)
  C24  .067(2)  .0580(19)  .0648(19)  -.0034(18)  .0044(17)  .0062(15)
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
  Cl1 C6 . 1.730(3) ?
  N1 C6 . 1.313(4) yes
  N1 C2 . 1.334(5) yes
  C2 N3 . 1.340(4) yes
  C2 H2 .  .9300 ?
  N3 C4 . 1.325(3) yes
  C4 N9 . 1.367(3) yes
  C4 C5 . 1.400(4) yes
  C5 N7 . 1.375(3) yes
  C5 C6 . 1.377(4) yes
  N7 C8 . 1.309(4) yes
  C8 N9 . 1.361(3) yes
  C8 H8 .  .9300 ?
  N9 C10 . 1.471(3) yes
  C10 C14 . 1.512(4) ?
  C10 C11 . 1.527(4) ?
  C10 H10 .  .9800 ?
  C11 C12 . 1.511(5) ?
  C11 H11A .  .9700 ?
  C11 H11B .  .9700 ?
  C12 O13 . 1.424(4) yes
  C12 H12A .  .9700 ?
  C12 H12B .  .9700 ?
  O13 C14 . 1.425(4) yes
  C14 C15 . 1.512(4) ?
  C14 H14 .  .9800 ?
  C15 C16 . 1.498(4) ?
  C15 H15A .  .9700 ?
  C15 H15B .  .9700 ?
  C16 O17 . 1.436(4) yes
  C16 H16A .  .9700 ?
  C16 H16B .  .9700 ?
  O17 C18 . 1.394(4) yes
  C18 C19 . 1.509(5) ?
  C18 H18A .  .9700 ?
  C18 H18B .  .9700 ?
  C19 C24 . 1.371(5) ?
  C19 C20 . 1.371(5) ?
  C20 C21 . 1.390(6) ?
  C20 H20 .  .9300 ?
  C21 C22 . 1.362(6) ?
  C21 H21 .  .9300 ?
  C22 C23 . 1.358(6) ?
  C22 H22 .  .9300 ?
  C23 C24 . 1.382(5) ?
  C23 H23 .  .9300 ?
  C24 H24 .  .9300 ?