#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:26:14 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178469 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/90/4029039.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_4029039
loop_
_publ_author_name
'Dugovic, Branislav'
'Leumann, Christian J.'
_publ_section_title
;
 A 6'-Fluoro-Substituent in Bicyclo-DNA Increases Affinity to
 Complementary RNA Presumably by CF-HC Pseudohydrogen Bonds.
;
_journal_issue                   3
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1271
_journal_paper_doi               10.1021/jo402690j
_journal_volume                  79
_journal_year                    2014
_chemical_absolute_configuration rm
_chemical_formula_sum            'C12 H15 F N2 O5'
_chemical_formula_weight         286.26
_chemical_name_systematic
;
 ?
;
_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_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2011-01-31T17:06:58-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.1167(17)
_cell_length_b                   13.975(2)
_cell_length_c                   14.558(2)
_cell_measurement_reflns_used    1655
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.1892
_cell_measurement_theta_min      2.0205
_cell_volume                     1244.4(4)
_computing_cell_refinement
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
        (compiled Oct 25 2010,18:11:34)
;
_computing_data_collection
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
        (compiled Oct 25 2010,18:11:34)
;
_computing_data_reduction
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
        (compiled Oct 25 2010,18:11:34)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 16.0965
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1141682
_diffrn_orient_matrix_UB_12      0.0064485
_diffrn_orient_matrix_UB_13      0.0071321
_diffrn_orient_matrix_UB_21      0.0040418
_diffrn_orient_matrix_UB_22      -0.0437418
_diffrn_orient_matrix_UB_23      0.024977
_diffrn_orient_matrix_UB_31      0.0221939
_diffrn_orient_matrix_UB_32      -0.0253181
_diffrn_orient_matrix_UB_33      -0.0413519
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1046
_diffrn_reflns_av_unetI/netI     0.0679
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9404
_diffrn_reflns_theta_full        25.34
_diffrn_reflns_theta_max         25.34
_diffrn_reflns_theta_min         2.02
_exptl_absorpt_coefficient_mu    0.129
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.56823
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
        (compiled Oct 25 2010,18:11:34)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.0995
_exptl_crystal_size_mid          0.0308
_exptl_crystal_size_min          0.0232
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         1348
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0827
_refine_ls_R_factor_gt           0.0589
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0690P)²+0.6343P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.13
_refine_ls_wR_factor_ref         0.1418
_reflns_number_gt                1050
_reflns_number_total             1348
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo402690j_si_002.cif
_cod_data_source_block           11cl001
_cod_original_cell_volume        1244.5(4)
_cod_database_code               4029039
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -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
C1 C 0.3338(9) 0.5403(4) 0.5736(3) 0.0226(12) Uani 1 1 d .
H1 H 0.4586 0.5801 0.5664 0.027 Uiso 1 1 calc R
C2 C 0.3148(9) 0.4630(4) 0.5190(3) 0.0239(12) Uani 1 1 d .
C3 C 0.1198(9) 0.4036(4) 0.5285(3) 0.0199(11) Uani 1 1 d .
C5 C -0.0076(9) 0.5119(4) 0.6529(4) 0.0243(13) Uani 1 1 d .
C7 C 0.4856(9) 0.4336(5) 0.4500(4) 0.0331(15) Uani 1 1 d .
H7A H 0.4392 0.3746 0.4193 0.05 Uiso 1 1 calc R
H7B H 0.6249 0.4225 0.4816 0.05 Uiso 1 1 calc R
H7C H 0.504 0.4844 0.4043 0.05 Uiso 1 1 calc R
C8 C 0.2068(9) 0.6533(4) 0.6928(3) 0.0222(12) Uani 1 1 d .
H8 H 0.0797 0.6602 0.7355 0.027 Uiso 1 1 calc R
C10 C 0.2854(9) 0.8126(4) 0.6847(3) 0.0195(12) Uani 1 1 d .
H10 H 0.1595 0.8501 0.7097 0.023 Uiso 1 1 calc R
C11 C 0.4274(9) 0.7715(4) 0.7636(3) 0.0213(12) Uani 1 1 d .
C12 C 0.4162(9) 0.6625(4) 0.7472(3) 0.0226(12) Uani 1 1 d .
H12A H 0.5437 0.6396 0.7116 0.027 Uiso 1 1 calc R
H12B H 0.4078 0.6269 0.8059 0.027 Uiso 1 1 calc R
C13 C 0.6562(10) 0.8161(4) 0.7483(3) 0.0315(14) Uani 1 1 d .
H13A H 0.6735 0.8752 0.7852 0.038 Uiso 1 1 calc R
H13B H 0.7727 0.7704 0.7657 0.038 Uiso 1 1 calc R
C14 C 0.6657(9) 0.8383(4) 0.6469(4) 0.0305(14) Uani 1 1 d .
H14 H 0.7803 0.8872 0.6328 0.037 Uiso 1 1 calc R
C15 C 0.4343(9) 0.8763(4) 0.6264(3) 0.0234(12) Uani 1 1 d .
H15 H 0.4248 0.9427 0.6516 0.028 Uiso 1 1 calc R
N4 N -0.0205(7) 0.4330(3) 0.5972(3) 0.0210(10) Uani 1 1 d .
H4 H -0.1344 0.3959 0.6066 0.025 Uiso 1 1 calc R
N6 N 0.1808(7) 0.5650(3) 0.6397(3) 0.0229(10) Uani 1 1 d .
O1 O 0.0741(7) 0.3327(3) 0.4826(2) 0.0341(10) Uani 1 1 d .
O2 O -0.1465(7) 0.5301(3) 0.7110(2) 0.0319(10) Uani 1 1 d .
O3 O 0.3796(7) 0.8807(3) 0.5323(2) 0.0312(10) Uani 1 1 d .
H3 H 0.4792 0.8551 0.5011 0.047 Uiso 1 1 calc R
O4 O 0.3348(7) 0.7971(3) 0.8499(2) 0.0311(10) Uani 1 1 d .
H4A H 0.4117 0.7744 0.8925 0.047 Uiso 1 1 calc R
O9 O 0.2095(6) 0.7327(2) 0.6314(2) 0.0222(9) Uani 1 1 d .
F1 F 0.6977(6) 0.7536(3) 0.5962(2) 0.0402(9) Uani 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 2 0.0366
-1 0 0 0.0496
1 0 0 0.0496
0 1 -1 0.0116
0 -1 1 0.0116
0 1 1 0.0199
0 -1 -1 0.0199
0 -1 -2 0.0068
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 C1 N6 123.4(5)
C1 C2 C3 118.1(5)
C1 C2 C7 123.6(5)
C3 C2 C7 118.3(5)
O1 C3 N4 119.6(5)
O1 C3 C2 126.4(5)
N4 C3 C2 114.0(4)
O2 C5 N4 122.4(5)
O2 C5 N6 124.2(5)
N4 C5 N6 113.3(5)
O9 C8 N6 109.1(4)
O9 C8 C12 104.6(4)
N6 C8 C12 116.1(4)
O9 C10 C15 110.1(4)
O9 C10 C11 107.1(4)
C15 C10 C11 107.0(4)
O4 C11 C12 111.5(4)
O4 C11 C13 112.7(4)
C12 C11 C13 114.6(4)
O4 C11 C10 109.7(4)
C12 C11 C10 103.1(4)
C13 C11 C10 104.6(4)
C8 C12 C11 101.7(4)
C14 C13 C11 105.0(4)
F1 C14 C13 110.2(5)
F1 C14 C15 108.3(4)
C13 C14 C15 103.0(5)
O3 C15 C10 115.0(4)
O3 C15 C14 114.9(5)
C10 C15 C14 103.8(4)
C5 N4 C3 129.2(5)
C5 N6 C1 121.8(4)
C5 N6 C8 117.9(4)
C1 N6 C8 120.2(4)
C8 O9 C10 105.6(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.346(7)
C1 N6 1.386(7)
C2 C3 1.460(8)
C2 C7 1.506(7)
C3 O1 1.226(6)
C3 N4 1.381(6)
C5 O2 1.225(6)
C5 N4 1.371(7)
C5 N6 1.384(7)
C8 O9 1.425(6)
C8 N6 1.465(7)
C8 C12 1.512(7)
C10 O9 1.436(6)
C10 C15 1.531(7)
C10 C11 1.550(7)
C11 O4 1.424(6)
C11 C12 1.543(7)
C11 C13 1.548(8)
C13 C14 1.510(7)
C14 F1 1.409(7)
C14 C15 1.541(8)
C15 O3 1.411(6)
