#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/58/1505841.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_1505841
loop_
_publ_author_name
'Alibés, Ramon'
'Alvárez-Larena, Angel'
'de March, Pedro'
'Figueredo, Marta'
'Font, Josep'
'Parella, Teodor'
'Rustullet, Albert'
_publ_section_title
;
 Synthesis and conformational analysis of new cyclobutane-fused
 nucleosides.
;
_journal_issue                   3
_journal_name_full               'Organic letters'
_journal_page_first              491
_journal_page_last               494
_journal_paper_doi               10.1021/ol052794y
_journal_volume                  8
_journal_year                    2006
_chemical_formula_sum            'C12 H15 N5 O2'
_chemical_formula_weight         261.29
_chemical_name_systematic
;
(1R,2R,4S,5S)-9-(4-hydroxymethyl-3-oxabicyclo[3.2.0]hept-2-yl)adenine
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.873(2)
_cell_length_b                   8.231(2)
_cell_length_c                   18.935(5)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      14.01
_cell_measurement_theta_min      10.05
_cell_volume                     1227.0(5)
_computing_cell_refinement       'CAD4 (Enraf-Nonius)'
_computing_data_collection       'CAD4 (Enraf-Nonius)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1985)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.837
_diffrn_measured_fraction_theta_max 0.837
_diffrn_measurement_device_type  'Enraf-Nonius CAD4'
_diffrn_measurement_method       'omega/2theta scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0178
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1049
_diffrn_reflns_theta_full        24.80
_diffrn_reflns_theta_max         24.80
_diffrn_reflns_theta_min         2.15
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  1.000
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.121
_refine_diff_density_min         -0.127
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   4.9(18)
_refine_ls_extinction_coef       0.009(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         1049
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0348
_refine_ls_R_factor_gt           0.0291
_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)+(0.0596P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0752
_refine_ls_wR_factor_ref         0.0762
_reflns_number_gt                927
_reflns_number_total             1049
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol052794ysi20051118_094225.cif
_cod_data_source_block           c315
_cod_depositor_comments
;
 Removing the "?" symbol from the _chemical_name_systematic data item value.

 Antanas Vaitkus,
 2017-03-30
;
_cod_database_code               1505841
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
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
C1 C 0.0049(3) 0.6676(3) 0.31320(12) 0.0427(5) Uani 1 1 d .
N2 N -0.0081(3) 0.8272(2) 0.33217(10) 0.0469(5) Uani 1 1 d .
C3 C 0.0141(4) 0.8687(3) 0.39996(14) 0.0477(6) Uani 1 1 d .
H3 H 0.0061 0.9792 0.4097 0.057 Uiso 1 1 calc R
N4 N 0.0459(3) 0.7741(2) 0.45525(10) 0.0447(5) Uani 1 1 d .
C5 C 0.0575(3) 0.6165(3) 0.43548(13) 0.0396(5) Uani 1 1 d .
N6 N 0.0895(2) 0.4847(2) 0.47807(10) 0.0400(4) Uani 1 1 d .
C7 C 0.0909(3) 0.3520(3) 0.43429(12) 0.0436(5) Uani 1 1 d .
H7 H 0.1105 0.2468 0.4503 0.052 Uiso 1 1 calc R
N8 N 0.0622(3) 0.3871(2) 0.36772(11) 0.0444(5) Uani 1 1 d .
C9 C 0.0399(3) 0.5551(3) 0.36774(12) 0.0395(5) Uani 1 1 d .
N10 N -0.0164(4) 0.6295(2) 0.24598(13) 0.0592(7) Uani 1 1 d D
H10A H -0.036(5) 0.713(4) 0.2155(17) 0.089 Uiso 1 1 d D
H10B H -0.001(5) 0.528(4) 0.2282(18) 0.089 Uiso 1 1 d D
C11 C 0.1231(3) 0.4952(3) 0.55433(13) 0.0425(5) Uani 1 1 d .
H11 H 0.1941 0.5909 0.5632 0.051 Uiso 1 1 calc R
O12 O 0.2140(2) 0.35499(19) 0.57576(9) 0.0447(4) Uani 1 1 d .
C13 C 0.1120(3) 0.2524(3) 0.62214(12) 0.0460(6) Uani 1 1 d .
H13 H 0.1832 0.2115 0.6607 0.055 Uiso 1 1 calc R
C14 C -0.0233(4) 0.3643(4) 0.65192(14) 0.0541(7) Uani 1 1 d .
H14 H -0.1317 0.3100 0.6612 0.065 Uiso 1 1 calc R
C15 C 0.0295(5) 0.4864(4) 0.71005(15) 0.0714(9) Uani 1 1 d .
H15A H -0.0384 0.4784 0.7527 0.086 Uiso 1 1 calc R
H15B H 0.1497 0.4837 0.7211 0.086 Uiso 1 1 calc R
C16 C -0.0211(5) 0.6278(4) 0.66240(16) 0.0681(9) Uani 1 1 d .
H16A H 0.0678 0.7083 0.6564 0.082 Uiso 1 1 calc R
H16B H -0.1275 0.6788 0.6757 0.082 Uiso 1 1 calc R
C17 C -0.0373(3) 0.5084(3) 0.59956(13) 0.0523(6) Uani 1 1 d .
H17 H -0.1443 0.5148 0.5732 0.063 Uiso 1 1 calc R
C18 C 0.0360(4) 0.1097(3) 0.58186(15) 0.0514(6) Uani 1 1 d .
H18A H -0.0263 0.0401 0.6141 0.062 Uiso 1 1 calc R
H18B H -0.0425 0.1493 0.5463 0.062 Uiso 1 1 calc R
O19 O 0.1675(3) 0.0203(3) 0.54925(12) 0.0658(6) Uani 1 1 d .
H19 H 0.116(5) -0.072(6) 0.525(2) 0.099 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N10 C1 N2 118.2(2)
N10 C1 C9 124.9(2)
N2 C1 C9 116.9(2)
C3 N2 C1 119.2(2)
N4 C3 N2 129.0(2)
C3 N4 C5 110.9(2)
N4 C5 N6 127.3(2)
N4 C5 C9 126.8(2)
N6 C5 C9 105.8(2)
C7 N6 C5 105.99(18)
C7 N6 C11 129.71(19)
C5 N6 C11 124.22(18)
N8 C7 N6 113.8(2)
C7 N8 C9 103.8(2)
C5 C9 N8 110.5(2)
C5 C9 C1 117.1(2)
N8 C9 C1 132.4(2)
O12 C11 N6 108.92(18)
O12 C11 C17 108.3(2)
N6 C11 C17 113.89(19)
C11 O12 C13 111.45(19)
O12 C13 C14 105.0(2)
O12 C13 C18 111.2(2)
C14 C13 C18 112.2(2)
C13 C14 C15 118.1(3)
C13 C14 C17 106.1(2)
C15 C14 C17 88.7(2)
C16 C15 C14 90.3(2)
C15 C16 C17 89.5(2)
C11 C17 C16 114.0(3)
C11 C17 C14 104.1(2)
C16 C17 C14 89.3(2)
O19 C18 C13 109.4(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N10 1.321(3)
C1 N2 1.366(3)
C1 C9 1.414(3)
N2 C3 1.340(3)
C3 N4 1.329(3)
N4 C5 1.353(3)
C5 N6 1.375(3)
C5 C9 1.386(3)
N6 C7 1.371(3)
N6 C11 1.471(3)
C7 N8 1.313(3)
N8 C9 1.394(3)
C11 O12 1.417(3)
C11 C17 1.530(4)
O12 C13 1.459(3)
C13 C14 1.517(4)
C13 C18 1.523(4)
C14 C15 1.547(4)
C14 C17 1.550(4)
C15 C16 1.525(4)
C16 C17 1.548(4)
C18 O19 1.412(3)
loop_
_cod_related_entry_id
_cod_related_entry_code
_cod_related_entry_database
1 21199903 ChemSpider
