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#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/29/1502952.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_1502952
loop_
_publ_author_name
'Alexander, Varughese'
'Choi, Won Jun'
'Chun, Jeongha'
'Kim, Hea Ok'
'Jeon, Ji Hye'
'Tosh, Dilip K.'
'Lee, Hyuk Woo'
'Chandra, Girish'
'Choi, Jungwon'
'Jeong, Lak Shin'
_publ_section_title
;
 A new DNA building block, 4'-selenothymidine: synthesis and modification
 to 4'-seleno-AZT as a potential anti-HIV agent.
;
_journal_issue                   10
_journal_name_full               'Organic letters'
_journal_page_first              2242
_journal_page_last               2245
_journal_paper_doi               10.1021/ol1005906
_journal_volume                  12
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_formula_sum            'C10 H14 N2 O4 Se'
_chemical_formula_weight         305.19
_chemical_name_systematic
; 
 ? 
;
_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
_audit_update_record
;
2010-04-08 # Formatted by publCIF
;
_cell_angle_alpha                90.00
_cell_angle_beta                 92.047(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.2745(7)
_cell_length_b                   5.2059(3)
_cell_length_c                   12.1233(7)
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.4
_cell_volume                     584.97(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      290(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku Rapid R-axis'
_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  0.0284
_diffrn_reflns_av_sigmaI/netI    0.0437
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5697
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.36
_exptl_absorpt_coefficient_mu    3.215
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.733
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.353
_refine_diff_density_min         -0.534
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.025(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.136
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2410
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.135
_refine_ls_R_factor_all          0.0304
_refine_ls_R_factor_gt           0.0251
_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)+(0.0149P)²+0.0174P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0496
_refine_ls_wR_factor_ref         0.0548
_reflns_number_gt                2196
_reflns_number_total             2410
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol1005906_si_001.cif
_cod_data_source_block           se-dt
_cod_original_cell_volume        584.97(6)
_cod_original_sg_symbol_H-M      P21
_cod_database_code               1502952
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
Se4' Se 0.77352(3) 0.04688(7) 0.67759(2) 0.03271(9) Uani 1 1 d .
C1' C 0.8516(3) 0.1765(6) 0.8216(2) 0.0265(6) Uani 1 1 d .
C4' C 0.5775(3) 0.1338(5) 0.7205(2) 0.0254(6) Uani 1 1 d .
H4' H 0.5158 -0.0175 0.7097 0.031 Uiso 1 1 calc R
O3' O 0.5929(2) -0.0314(4) 0.91068(17) 0.0360(6) Uani 1 1 d .
O4 O 1.3333(2) 0.7869(4) 0.82735(18) 0.0426(6) Uani 1 1 d .
N1 N 0.9864(2) 0.3237(4) 0.81288(19) 0.0249(5) Uani 1 1 d .
N3 N 1.2039(3) 0.4574(5) 0.8944(2) 0.0281(5) Uani 1 1 d .
C3' C 0.5902(3) 0.1951(6) 0.8448(2) 0.0263(6) Uani 1 1 d .
O5' O 0.5068(3) 0.2880(4) 0.54113(16) 0.0472(6) Uani 1 1 d .
H5' H 0.5046 0.4198 0.5041 0.071 Uiso 1 1 calc R
O2 O 1.0731(2) 0.1452(4) 0.97470(16) 0.0368(5) Uani 1 1 d .
C2' C 0.7296(3) 0.3366(5) 0.8676(2) 0.0271(6) Uani 1 1 d .
H2'1 H 0.7454 0.3611 0.9464 0.033 Uiso 1 1 calc R
H2'2 H 0.7261 0.5040 0.8324 0.033 Uiso 1 1 calc R
C5' C 0.5134(4) 0.3527(6) 0.6550(3) 0.0360(8) Uani 1 1 d .
H1' H 0.877(3) 0.007(6) 0.870(2) 0.023(8) Uiso 1 1 d .
H6 H 0.925(3) 0.497(5) 0.6702(19) 0.022(7) Uiso 1 1 d .
H3 H 1.267(3) 0.444(5) 0.947(2) 0.018(7) Uiso 1 1 d .
H52' H 0.414(4) 0.381(7) 0.678(3) 0.047(10) Uiso 1 1 d .
H3' H 0.507(4) 0.306(6) 0.873(3) 0.037(9) Uiso 1 1 d .
H30' H 0.514(4) -0.099(7) 0.891(3) 0.037(10) Uiso 1 1 d .
H51' H 0.571(3) 0.491(6) 0.667(2) 0.031(9) Uiso 1 1 d .
C2 C 1.0862(3) 0.2973(5) 0.9001(2) 0.0255(6) Uani 1 1 d .
C4 C 1.2268(3) 0.6463(6) 0.8174(2) 0.0287(6) Uani 1 1 d .
C5 C 1.1204(3) 0.6590(5) 0.7279(2) 0.0277(6) Uani 1 1 d .
C6 C 1.0057(3) 0.5033(6) 0.7312(2) 0.0285(7) Uani 1 1 d .
C7 C 1.1453(4) 0.8428(7) 0.6352(3) 0.0416(8) Uani 1 1 d .
H7A H 1.0631 0.8418 0.5848 0.062 Uiso 1 1 calc R
H7B H 1.2296 0.7914 0.5971 0.062 Uiso 1 1 calc R
H7C H 1.1593 1.0127 0.6645 0.062 Uiso 1 1 calc R
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'
O O 0.0106 0.0060 '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'
Se Se -0.0929 2.2259 '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
C4' Se4' C1' 90.03(12)
N1 C1' C2' 112.6(2)
N1 C1' Se4' 113.43(18)
C2' C1' Se4' 104.79(19)
C5' C4' C3' 112.1(2)
C5' C4' Se4' 112.9(2)
C3' C4' Se4' 105.54(18)
C6 N1 C2 120.9(2)
C6 N1 C1' 122.5(2)
C2 N1 C1' 116.0(2)
C4 N3 C2 127.4(2)
O3' C3' C2' 107.7(2)
O3' C3' C4' 112.1(2)
C2' C3' C4' 108.4(2)
C3' C2' C1' 108.0(2)
O5' C5' C4' 109.7(2)
O2 C2 N3 122.3(3)
O2 C2 N1 123.5(3)
N3 C2 N1 114.2(3)
O4 C4 N3 120.0(3)
O4 C4 C5 124.8(3)
N3 C4 C5 115.2(3)
C6 C5 C4 118.2(3)
C6 C5 C7 123.6(3)
C4 C5 C7 118.3(3)
C5 C6 N1 123.8(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Se4' C4' 1.962(3)
Se4' C1' 1.984(3)
C1' N1 1.474(4)
C1' C2' 1.527(4)
C4' C5' 1.500(4)
C4' C3' 1.540(4)
O3' C3' 1.424(3)
O4 C4 1.232(3)
N1 C6 1.378(4)
N1 C2 1.387(4)
N3 C4 1.377(4)
N3 C2 1.377(4)
C3' C2' 1.505(4)
O5' C5' 1.420(4)
O2 C2 1.212(3)
C4 C5 1.442(4)
C5 C6 1.339(4)
C5 C7 1.500(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
C4' Se4' C1' N1 -139.3(2)
C4' Se4' C1' C2' -16.12(19)
C1' Se4' C4' C5' 111.2(2)
C1' Se4' C4' C3' -11.55(19)
C2' C1' N1 C6 -75.3(3)
Se4' C1' N1 C6 43.4(3)
C2' C1' N1 C2 96.3(3)
Se4' C1' N1 C2 -145.0(2)
C5' C4' C3' O3' 155.9(3)
Se4' C4' C3' O3' -80.9(3)
C5' C4' C3' C2' -85.3(3)
Se4' C4' C3' C2' 37.9(3)
O3' C3' C2' C1' 68.0(3)
C4' C3' C2' C1' -53.6(3)
N1 C1' C2' C3' 165.0(2)
Se4' C1' C2' C3' 41.3(3)
C3' C4' C5' O5' 178.9(3)
Se4' C4' C5' O5' 59.9(3)
C4 N3 C2 O2 -176.2(3)
C4 N3 C2 N1 4.7(4)
C6 N1 C2 O2 178.9(3)
C1' N1 C2 O2 7.1(4)
C6 N1 C2 N3 -2.0(4)
C1' N1 C2 N3 -173.7(2)
C2 N3 C4 O4 174.9(3)
C2 N3 C4 C5 -6.1(4)
O4 C4 C5 C6 -176.3(3)
N3 C4 C5 C6 4.8(4)
O4 C4 C5 C7 4.7(5)
N3 C4 C5 C7 -174.2(2)
C4 C5 C6 N1 -2.9(4)
C7 C5 C6 N1 176.1(3)
C2 N1 C6 C5 1.4(4)
C1' N1 C6 C5 172.6(3)
