#------------------------------------------------------------------------------
#$Date: 2016-03-22 11:56:50 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178925 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/54/4115461.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_4115461
loop_
_publ_author_name
'Lakshmaiah Gingipalli'
'Peter C. Dedon'
_publ_section_title
;
 Reaction of cis- and trans-2-Butene-1,4-dial with 2'-Deoxycytidine to
 Form Stable Oxadiazabicyclooctaimine Adducts
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2664
_journal_page_last               2665
_journal_paper_doi               10.1021/ja0056421
_journal_volume                  123
_journal_year                    2001
_chemical_formula_sum            'C9 H11 N3 O3'
_chemical_formula_weight         209.21
_chemical_name_systematic
;
    ?
;
_space_group_IT_number           43
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'F 2 -2d'
_symmetry_space_group_name_H-M   'F d d 2'
_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            16
_cell_length_a                   21.523(2)
_cell_length_b                   23.449(3)
_cell_length_c                   7.3211(8)
_cell_measurement_temperature    183(2)
_cell_volume                     3694.9(7)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      183(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0489
_diffrn_reflns_av_sigmaI/netI    0.0368
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            3673
_diffrn_reflns_theta_full        23.27
_diffrn_reflns_theta_max         23.27
_diffrn_reflns_theta_min         2.57
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_description       parallelpip
_exptl_crystal_F_000             1760
_exptl_crystal_size_max          .28
_exptl_crystal_size_mid          .10
_exptl_crystal_size_min          .10
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1(2)
_refine_ls_extinction_coef       0.00016(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.145
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         1303
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.145
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0435
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0387P)²+7.2342P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0960
_refine_ls_wR_factor_ref         0.0971
_reflns_number_gt                1232
_reflns_number_total             1303
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0056421.cif
_cod_data_source_block           00182t
_cod_database_code               4115461
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'
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
O1 O 1.10056(10) 0.12987(9) -0.0600(3) 0.0351(6) Uani 1 1 d .
O2 O 0.88468(10) 0.16504(10) 0.2091(3) 0.0340(6) Uani 1 1 d .
O3 O 1.08144(12) 0.03513(11) 0.0141(4) 0.0448(7) Uani 1 1 d .
H3 H 1.1069 0.0156 -0.0462 0.067 Uiso 1 1 calc R
N1 N 1.08196(12) 0.21923(12) 0.0802(4) 0.0306(7) Uani 1 1 d .
N2 N 0.89952(12) 0.25932(11) 0.1383(4) 0.0297(7) Uani 1 1 d .
N3 N 0.98054(12) 0.19511(10) 0.1221(4) 0.0240(7) Uani 1 1 d .
C1 C 1.08076(15) 0.15770(13) 0.1048(5) 0.0279(8) Uani 1 1 d .
H1 H 1.1071 0.1460 0.2108 0.033 Uiso 1 1 calc R
C2 C 1.02494(16) 0.23733(13) 0.0897(5) 0.0257(8) Uani 1 1 d .
C3 C 1.00158(16) 0.29397(15) 0.0731(5) 0.0300(9) Uani 1 1 d .
H3A H 1.0285 0.3250 0.0463 0.036 Uiso 1 1 calc R
C4 C 0.94045(17) 0.30209(14) 0.0964(5) 0.0323(9) Uani 1 1 d .
H4 H 0.9246 0.3397 0.0831 0.039 Uiso 1 1 calc R
C5 C 0.91922(15) 0.20360(14) 0.1590(4) 0.0276(8) Uani 1 1 d .
C6 C 1.01203(14) 0.13975(13) 0.1344(5) 0.0267(8) Uani 1 1 d .
H6 H 1.0056 0.1213 0.2561 0.032 Uiso 1 1 calc R
C7 C 0.99760(16) 0.09899(14) -0.0227(5) 0.0321(9) Uani 1 1 d .
H7A H 0.9743 0.1186 -0.1211 0.039 Uiso 1 1 calc R
H7B H 0.9732 0.0658 0.0203 0.039 Uiso 1 1 calc R
C8 C 1.06235(16) 0.08060(14) -0.0884(5) 0.0327(9) Uani 1 1 d .
H8 H 1.0612 0.0702 -0.2209 0.039 Uiso 1 1 calc R
C9 C 0.83400(14) 0.27164(16) 0.1730(5) 0.0387(10) Uani 1 1 d .
H9A H 0.8254 0.3116 0.1432 0.058 Uiso 1 1 calc R
H9B H 0.8247 0.2648 0.3021 0.058 Uiso 1 1 calc R
H9C H 0.8081 0.2468 0.0970 0.058 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'
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
C8 O1 C1 108.5(3)
C2 N1 C1 107.5(3)
C4 N2 C5 121.3(3)
C4 N2 C9 121.0(3)
C5 N2 C9 117.6(3)
C5 N3 C2 126.4(3)
C5 N3 C6 124.4(3)
C2 N3 C6 108.8(2)
O1 C1 N1 110.0(3)
O1 C1 C6 106.0(3)
N1 C1 C6 107.6(3)
N1 C2 N3 115.1(3)
N1 C2 C3 129.2(3)
N3 C2 C3 115.7(3)
C4 C3 C2 117.9(3)
C3 C4 N2 123.8(3)
O2 C5 N3 122.6(3)
O2 C5 N2 122.9(3)
N3 C5 N2 114.4(3)
N3 C6 C7 114.4(3)
N3 C6 C1 101.1(2)
C7 C6 C1 105.0(3)
C6 C7 C8 103.1(3)
O3 C8 O1 112.1(3)
O3 C8 C7 108.6(3)
O1 C8 C7 104.4(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C8 1.433(4)
O1 C1 1.437(4)
O2 C5 1.227(4)
O3 C8 1.367(4)
N1 C2 1.300(4)
N1 C1 1.454(4)
N2 C4 1.370(4)
N2 C5 1.382(4)
N2 C9 1.462(4)
N3 C5 1.362(4)
N3 C2 1.396(4)
N3 C6 1.467(4)
C1 C6 1.553(4)
C2 C3 1.425(5)
C3 C4 1.340(5)
C6 C7 1.527(5)
C7 C8 1.536(5)
