#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:03:47 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178418 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/39/4023959.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_4023959
loop_
_publ_author_name
'Weibing Lu'
'Sujata Sengupta'
'Jeffrey L. Petersen'
'Novruz G. Akhmedov'
'Xiaodong Shi'
_publ_section_title
;
 Mitsunobu Coupling of Nucleobases and Alcohols: An Efficient,
 Practical Synthesis for Novel Nonsugar Carbon Nucleosides
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5012
_journal_page_last               5015
_journal_paper_doi               10.1021/jo070515+
_journal_volume                  72
_journal_year                    2007
_chemical_formula_sum            'C14 H10 Cl2 N4'
_chemical_formula_weight         305.16
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                98.359(3)
_cell_angle_beta                 103.597(3)
_cell_angle_gamma                97.752(3)
_cell_formula_units_Z            4
_cell_length_a                   7.5555(12)
_cell_length_b                   12.711(2)
_cell_length_c                   14.920(3)
_cell_measurement_reflns_used    4636
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.36
_cell_volume                     1356.5(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.960
_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  0.0314
_diffrn_reflns_av_sigmaI/netI    0.0590
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9424
_diffrn_reflns_theta_full        27.52
_diffrn_reflns_theta_max         27.52
_diffrn_reflns_theta_min         1.97
_exptl_absorpt_coefficient_mu    0.472
_exptl_absorpt_correction_type   semi-empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.560
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         5994
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.1005
_refine_ls_R_factor_gt           0.0618
_refine_ls_shift/su_max          0.076
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1005P)²+0.2291P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1611
_refine_ls_wR_factor_ref         0.1865
_reflns_number_gt                3767
_reflns_number_total             5994
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo070515+si20070312_112653.cif
_cod_data_source_block           ms13ccd
_cod_database_code               4023959
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.80488(10) -0.30850(5) 0.44579(6) 0.0865(2) Uani 1 1 d . . .
Cl2 Cl 0.35755(6) -0.03744(5) 0.38272(4) 0.05903(15) Uani 1 1 d . . .
N1 N 0.9190(2) -0.12584(15) 0.40037(13) 0.0610(5) Uani 1 1 d . . .
N2 N 0.6059(2) -0.16164(14) 0.41072(12) 0.0531(5) Uani 1 1 d . . .
N3 N 1.0074(2) 0.04613(17) 0.35674(15) 0.0718(6) Uani 1 1 d . . .
N4 N 0.7310(2) 0.10140(15) 0.34353(13) 0.0580(5) Uani 1 1 d . . .
C1 C 0.7744(3) -0.18291(18) 0.41562(15) 0.0563(6) Uani 1 1 d . . .
C2 C 0.5747(2) -0.06807(16) 0.38816(13) 0.0452(5) Uani 1 1 d . . .
C3 C 0.7117(2) 0.00285(17) 0.37001(13) 0.0471(5) Uani 1 1 d . . .
C4 C 0.9133(3) 0.1216(2) 0.33895(18) 0.0697(7) Uani 1 1 d . . .
H4 H 0.9645 0.1854 0.3240 0.084 Uiso 1 1 calc R . .
C5 C 0.8853(2) -0.03051(18) 0.37753(15) 0.0541(6) Uani 1 1 d . . .
C6 C 0.5976(3) 0.1774(2) 0.33433(18) 0.0740(7) Uani 1 1 d . . .
H6 H 0.4708 0.1369 0.3123 0.089 Uiso 1 1 calc R . .
C7 C 0.6320(3) 0.25152(19) 0.26785(16) 0.0598(6) Uani 1 1 d . . .
C8 C 0.5987(4) 0.2276(2) 0.17183(18) 0.0745(8) Uani 1 1 d . . .
H8 H 0.5486 0.1575 0.1398 0.089 Uiso 1 1 calc R . .
C9 C 0.6399(4) 0.3076(2) 0.12332(18) 0.0815(9) Uani 1 1 d . . .
H9 H 0.6200 0.2913 0.0585 0.098 Uiso 1 1 calc R . .
C10 C 0.7105(4) 0.4119(2) 0.17028(18) 0.0745(8) Uani 1 1 d . . .
H10 H 0.7351 0.4658 0.1367 0.089 Uiso 1 1 calc R . .
C11 C 0.7446(3) 0.4369(2) 0.26533(17) 0.0672(7) Uani 1 1 d . . .
H11 H 0.7954 0.5071 0.2966 0.081 Uiso 1 1 calc R . .
C12 C 0.7035(3) 0.3574(2) 0.31516(16) 0.0612(6) Uani 1 1 d . . .
C13 C 0.7267(4) 0.3641(2) 0.41938(18) 0.0895(9) Uani 1 1 d . . .
H13A H 0.6749 0.4238 0.4449 0.107 Uiso 1 1 calc R . .
H13B H 0.8562 0.3729 0.4525 0.107 Uiso 1 1 calc R . .
C14 C 0.6197(5) 0.2556(3) 0.4263(2) 0.1183(10) Uani 1 1 d . . .
H14A H 0.4993 0.2644 0.4356 0.142 Uiso 1 1 calc R . .
H14B H 0.6869 0.2278 0.4790 0.142 Uiso 1 1 calc R . .
Cl3 Cl 0.00757(12) 0.08996(6) 0.11556(6) 0.0970(3) Uani 1 1 d . . .
Cl4 Cl 0.25898(10) 0.45008(6) 0.35207(4) 0.0780(2) Uani 1 1 d . . .
N5 N 0.1086(3) 0.26420(16) 0.05654(14) 0.0679(6) Uani 1 1 d . . .
N6 N 0.1370(3) 0.27864(15) 0.22154(13) 0.0627(5) Uani 1 1 d . . .
N7 N 0.2093(4) 0.43075(18) 0.00894(14) 0.0856(8) Uani 1 1 d . . .
N8 N 0.2928(3) 0.53683(15) 0.15272(12) 0.0603(5) Uani 1 1 d . . .
C15 C 0.0951(3) 0.2279(2) 0.13214(18) 0.0660(7) Uani 1 1 d . . .
C16 C 0.2043(3) 0.38346(19) 0.23725(15) 0.0567(6) Uani 1 1 d . . .
C17 C 0.2265(3) 0.43489(18) 0.16439(14) 0.0541(6) Uani 1 1 d . . .
C18 C 0.2755(4) 0.5278(2) 0.05972(17) 0.0830(9) Uani 1 1 d . . .
H18 H 0.3086 0.5867 0.0331 0.100 Uiso 1 1 calc R . .
C19 C 0.1781(3) 0.37036(19) 0.07421(15) 0.0621(6) Uani 1 1 d . . .
C20 C 0.3514(3) 0.63818(19) 0.22485(15) 0.0613(6) Uani 1 1 d . . .
H20 H 0.4394 0.6271 0.2809 0.074 Uiso 1 1 calc R . .
C21 C 0.4352(3) 0.72858(17) 0.18423(15) 0.0546(6) Uani 1 1 d . . .
C22 C 0.6085(3) 0.74544(19) 0.16691(17) 0.0619(6) Uani 1 1 d . . .
H22 H 0.6907 0.6985 0.1818 0.074 Uiso 1 1 calc R . .
C23 C 0.6567(3) 0.8328(2) 0.12727(18) 0.0677(7) Uani 1 1 d . . .
H23 H 0.7724 0.8450 0.1153 0.081 Uiso 1 1 calc R . .
C24 C 0.5354(4) 0.9016(2) 0.10544(18) 0.0734(8) Uani 1 1 d . . .
H24 H 0.5700 0.9604 0.0789 0.088 Uiso 1 1 calc R . .
C25 C 0.3619(4) 0.8854(2) 0.12212(18) 0.0743(8) Uani 1 1 d . . .
H25 H 0.2800 0.9324 0.1066 0.089 Uiso 1 1 calc R . .
C26 C 0.3124(3) 0.79830(19) 0.16210(16) 0.0601(6) Uani 1 1 d . . .
C27 C 0.1337(3) 0.7617(2) 0.18780(18) 0.0772(8) Uani 1 1 d . . .
H27A H 0.0355 0.7281 0.1323 0.093 Uiso 1 1 calc R . .
H27B H 0.0945 0.8220 0.2211 0.093 Uiso 1 1 calc R . .
C28 C 0.1846(3) 0.6803(2) 0.25080(18) 0.0775(8) Uani 1 1 d . . .
H28A H 0.0816 0.6213 0.2400 0.093 Uiso 1 1 calc R . .
H28B H 0.2173 0.7146 0.3163 0.093 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'
Cl Cl 0.1484 0.1585 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C5 112.47(18) . . ?
C2 N2 C1 116.55(18) . . ?
C4 N3 C5 103.80(18) . . ?
C3 N4 C4 104.34(18) . . ?
C3 N4 C6 128.37(17) . . ?
C4 N4 C6 126.8(2) . . ?
N1 C1 N2 130.4(2) . . ?
N1 C1 Cl1 115.80(17) . . ?
N2 C1 Cl1 113.82(17) . . ?
N2 C2 C3 121.05(17) . . ?
N2 C2 Cl2 117.58(15) . . ?
C3 C2 Cl2 121.37(16) . . ?
N4 C3 C2 137.91(18) . . ?
N4 C3 C5 105.69(17) . . ?
C2 C3 C5 116.38(19) . . ?
N3 C4 N4 115.7(2) . . ?
N1 C5 N3 126.35(19) . . ?
N1 C5 C3 123.18(19) . . ?
N3 C5 C3 110.5(2) . . ?
N4 C6 C7 111.23(19) . . ?
N4 C6 C14 112.6(2) . . ?
C7 C6 C14 103.2(2) . . ?
C8 C7 C12 119.8(2) . . ?
C8 C7 C6 128.7(2) . . ?
C12 C7 C6 111.6(2) . . ?
C9 C8 C7 119.8(2) . . ?
C8 C9 C10 120.3(2) . . ?
C11 C10 C9 120.7(3) . . ?
C10 C11 C12 119.8(2) . . ?
C11 C12 C7 119.7(2) . . ?
C11 C12 C13 130.1(2) . . ?
C7 C12 C13 110.2(2) . . ?
C12 C13 C14 103.6(2) . . ?
C13 C14 C6 107.5(2) . . ?
C15 N5 C19 112.3(2) . . ?
C16 N6 C15 115.9(2) . . ?
C18 N7 C19 102.8(2) . . ?
C18 N8 C17 104.81(18) . . ?
C18 N8 C20 127.0(2) . . ?
C17 N8 C20 127.84(18) . . ?
N5 C15 N6 130.8(2) . . ?
N5 C15 Cl3 115.33(18) . . ?
N6 C15 Cl3 113.90(19) . . ?
N6 C16 C17 120.8(2) . . ?
N6 C16 Cl4 116.46(17) . . ?
C17 C16 Cl4 122.76(17) . . ?
N8 C17 C16 137.74(19) . . ?
N8 C17 C19 105.46(19) . . ?
C16 C17 C19 116.7(2) . . ?
N7 C18 N8 116.1(2) . . ?
N5 C19 N7 125.7(2) . . ?
N5 C19 C17 123.5(2) . . ?
N7 C19 C17 110.8(2) . . ?
N8 C20 C21 109.88(18) . . ?
N8 C20 C28 111.86(18) . . ?
C21 C20 C28 103.0(2) . . ?
C26 C21 C22 120.7(2) . . ?
C26 C21 C20 111.0(2) . . ?
C22 C21 C20 128.3(2) . . ?
C23 C22 C21 119.0(2) . . ?
C24 C23 C22 120.3(2) . . ?
C23 C24 C25 121.2(3) . . ?
C26 C25 C24 118.9(2) . . ?
C25 C26 C21 119.9(2) . . ?
C25 C26 C27 130.0(2) . . ?
C21 C26 C27 110.1(2) . . ?
C26 C27 C28 103.5(2) . . ?
C27 C28 C20 106.0(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C1 1.750(2) . ?
Cl2 C2 1.7229(18) . ?
N1 C1 1.312(3) . ?
N1 C5 1.346(3) . ?
N2 C2 1.319(3) . ?
N2 C1 1.324(3) . ?
N3 C4 1.290(3) . ?
N3 C5 1.370(3) . ?
N4 C3 1.367(3) . ?
N4 C4 1.386(3) . ?
N4 C6 1.485(3) . ?
C2 C3 1.382(3) . ?
C3 C5 1.417(3) . ?
C6 C7 1.505(4) . ?
C6 C14 1.533(4) . ?
C7 C8 1.375(3) . ?
C7 C12 1.396(3) . ?
C8 C9 1.375(4) . ?
C9 C10 1.377(4) . ?
C10 C11 1.361(3) . ?
C11 C12 1.383(4) . ?
C12 C13 1.512(3) . ?
C13 C14 1.532(4) . ?
Cl3 C15 1.749(2) . ?
Cl4 C16 1.724(2) . ?
N5 C15 1.299(3) . ?
N5 C19 1.344(3) . ?
N6 C16 1.326(3) . ?
N6 C15 1.338(3) . ?
N7 C18 1.315(3) . ?
N7 C19 1.367(3) . ?
N8 C18 1.349(3) . ?
N8 C17 1.375(3) . ?
N8 C20 1.494(3) . ?
C16 C17 1.378(3) . ?
C17 C19 1.408(3) . ?
C20 C21 1.509(3) . ?
C20 C28 1.541(4) . ?
C21 C26 1.385(3) . ?
C21 C22 1.388(3) . ?
C22 C23 1.378(4) . ?
C23 C24 1.368(4) . ?
C24 C25 1.385(4) . ?
C25 C26 1.381(4) . ?
C26 C27 1.521(3) . ?
C27 C28 1.524(4) . ?
