#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:03:47 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178418 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/39/4023958.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_4023958
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            'C15 H12 Cl2 N4'
_chemical_formula_weight         319.19
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 105.444(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   17.4807(15)
_cell_length_b                   11.8848(10)
_cell_length_c                   14.4491(12)
_cell_measurement_reflns_used    7522
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.37
_cell_measurement_theta_min      2.25
_cell_volume                     2893.5(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 0.993
_diffrn_measured_fraction_theta_max 0.993
_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  0.0475
_diffrn_reflns_av_sigmaI/netI    0.0565
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            20219
_diffrn_reflns_theta_full        27.54
_diffrn_reflns_theta_max         27.54
_diffrn_reflns_theta_min         2.10
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.446
_exptl_absorpt_correction_type   semi-empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.465
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         6627
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.996
_refine_ls_R_factor_all          0.0844
_refine_ls_R_factor_gt           0.0459
_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)+(0.0479P)²+0.5433P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1045
_refine_ls_wR_factor_ref         0.1225
_reflns_number_gt                4204
_reflns_number_total             6627
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo070515+si20070312_112640.cif
_cod_data_source_block           ms12ccd
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4023958
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, 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
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.12526(5) 0.50688(6) 0.52995(5) 0.0764(2) Uani 1 1 d . . .
Cl2 Cl 0.34791(4) 0.22831(6) 0.51158(4) 0.0687(2) Uani 1 1 d . . .
Cl3 Cl 0.36550(4) 0.51425(5) 0.19958(4) 0.06258(19) Uani 1 1 d . . .
Cl4 Cl 0.14751(4) 0.78881(7) 0.24207(4) 0.0762(2) Uani 1 1 d . . .
N1 N 0.14115(11) 0.44616(14) 0.36315(12) 0.0465(4) Uani 1 1 d . . .
N2 N 0.23301(11) 0.37035(15) 0.50411(12) 0.0503(5) Uani 1 1 d . . .
N3 N 0.27090(11) 0.26274(15) 0.27989(12) 0.0498(4) Uani 1 1 d . . .
N4 N 0.16396(10) 0.37264(13) 0.21589(11) 0.0411(4) Uani 1 1 d . . .
N5 N 0.35870(11) 0.56953(14) 0.37152(11) 0.0453(4) Uani 1 1 d . . .
N6 N 0.26077(11) 0.64809(15) 0.23713(12) 0.0485(4) Uani 1 1 d . . .
N7 N 0.23488(12) 0.74709(16) 0.46999(13) 0.0541(5) Uani 1 1 d . . .
N8 N 0.34289(10) 0.63530(13) 0.52423(11) 0.0438(4) Uani 1 1 d . . .
C1 C 0.17193(14) 0.43314(18) 0.45665(15) 0.0492(5) Uani 1 1 d . . .
C2 C 0.27003(12) 0.31216(18) 0.45114(14) 0.0454(5) Uani 1 1 d . . .
C3 C 0.24658(12) 0.31607(16) 0.35180(14) 0.0406(5) Uani 1 1 d . . .
C4 C 0.21983(13) 0.29870(18) 0.20126(14) 0.0473(5) Uani 1 1 d . . .
H4 H 0.2215 0.2757 0.1403 0.057 Uiso 1 1 calc R . .
C5 C 0.18053(12) 0.38450(16) 0.31360(13) 0.0395(5) Uani 1 1 d . . .
C6 C 0.09460(12) 0.42332(17) 0.14493(13) 0.0437(5) Uani 1 1 d . . .
H6 H 0.0923 0.5033 0.1606 0.052 Uiso 1 1 calc R . .
C7 C 0.10598(12) 0.41494(16) 0.04473(13) 0.0412(5) Uani 1 1 d . . .
C8 C 0.16165(13) 0.48394(18) 0.01994(15) 0.0475(5) Uani 1 1 d . . .
H8 H 0.1911 0.5341 0.0649 0.057 Uiso 1 1 calc R . .
C9 C 0.17374(14) 0.47908(19) -0.07037(16) 0.0529(6) Uani 1 1 d . . .
H9 H 0.2117 0.5248 -0.0859 0.064 Uiso 1 1 calc R . .
C10 C 0.12901(15) 0.4057(2) -0.13798(16) 0.0561(6) Uani 1 1 d . . .
H10 H 0.1366 0.4022 -0.1992 0.067 Uiso 1 1 calc R . .
C11 C 0.07344(15) 0.33819(18) -0.11404(15) 0.0544(6) Uani 1 1 d . . .
H11 H 0.0435 0.2895 -0.1600 0.065 Uiso 1 1 calc R . .
C12 C 0.06055(13) 0.34040(17) -0.02295(14) 0.0455(5) Uani 1 1 d . . .
C13 C -0.00170(15) 0.2654(2) -0.00042(16) 0.0585(6) Uani 1 1 d . . .
H13A H 0.0012 0.1917 -0.0280 0.070 Uiso 1 1 calc R . .
H13B H -0.0538 0.2964 -0.0303 0.070 Uiso 1 1 calc R . .
C14 C 0.00777(15) 0.2527(2) 0.10684(17) 0.0602(6) Uani 1 1 d . . .
H14A H -0.0388 0.2164 0.1176 0.072 Uiso 1 1 calc R . .
H14B H 0.0536 0.2061 0.1351 0.072 Uiso 1 1 calc R . .
C15 C 0.01837(13) 0.36819(19) 0.15345(16) 0.0538(6) Uani 1 1 d . . .
H15A H 0.0197 0.3610 0.2207 0.065 Uiso 1 1 calc R . .
H15B H -0.0264 0.4155 0.1228 0.065 Uiso 1 1 calc R . .
C16 C 0.32331(13) 0.58545(17) 0.27907(14) 0.0455(5) Uani 1 1 d . . .
C17 C 0.22726(13) 0.70472(18) 0.29508(14) 0.0461(5) Uani 1 1 d . . .
C18 C 0.25595(12) 0.69802(17) 0.39376(14) 0.0419(5) Uani 1 1 d . . .
C19 C 0.28805(14) 0.70754(18) 0.54489(15) 0.0513(5) Uani 1 1 d . . .
H19 H 0.2887 0.7269 0.6075 0.062 Uiso 1 1 calc R . .
C20 C 0.32216(12) 0.62906(16) 0.42608(13) 0.0405(5) Uani 1 1 d . . .
C21 C 0.41456(13) 0.58368(18) 0.59005(14) 0.0470(5) Uani 1 1 d . . .
H21 H 0.4176 0.5052 0.5706 0.056 Uiso 1 1 calc R . .
C22 C 0.40724(13) 0.58455(16) 0.69257(13) 0.0431(5) Uani 1 1 d . . .
C23 C 0.35754(14) 0.50750(18) 0.71943(15) 0.0527(6) Uani 1 1 d . . .
H23 H 0.3287 0.4572 0.6741 0.063 Uiso 1 1 calc R . .
C24 C 0.35012(15) 0.5040(2) 0.81201(16) 0.0591(6) Uani 1 1 d . . .
H24 H 0.3166 0.4519 0.8291 0.071 Uiso 1 1 calc R . .
C25 C 0.39306(16) 0.5786(2) 0.87905(16) 0.0619(7) Uani 1 1 d . . .
H25 H 0.3884 0.5772 0.9417 0.074 Uiso 1 1 calc R . .
C26 C 0.44274(14) 0.6551(2) 0.85331(15) 0.0556(6) Uani 1 1 d . . .
H26 H 0.4718 0.7044 0.8995 0.067 Uiso 1 1 calc R . .
C27 C 0.45081(12) 0.66089(17) 0.75986(14) 0.0454(5) Uani 1 1 d . . .
C28 C 0.50719(15) 0.74482(19) 0.73519(16) 0.0570(6) Uani 1 1 d . . .
H28A H 0.5613 0.7210 0.7647 0.068 Uiso 1 1 calc R . .
H28B H 0.4996 0.8174 0.7622 0.068 Uiso 1 1 calc R . .
C29 C 0.49605(15) 0.7582(2) 0.62790(17) 0.0605(6) Uani 1 1 d . . .
H29A H 0.4487 0.8022 0.6006 0.073 Uiso 1 1 calc R . .
H29B H 0.5411 0.7979 0.6165 0.073 Uiso 1 1 calc R . .
C30 C 0.48843(14) 0.6440(2) 0.58002(16) 0.0576(6) Uani 1 1 d . . .
H30A H 0.5349 0.5990 0.6092 0.069 Uiso 1 1 calc R . .
H30B H 0.4857 0.6532 0.5125 0.069 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 110.82(18) . . ?
C2 N2 C1 116.34(18) . . ?
C4 N3 C3 103.14(17) . . ?
C5 N4 C4 105.11(16) . . ?
C5 N4 C6 125.24(16) . . ?
C4 N4 C6 129.43(16) . . ?
C16 N5 C20 110.43(18) . . ?
C17 N6 C16 116.41(18) . . ?
C19 N7 C18 103.05(18) . . ?
C20 N8 C19 104.52(16) . . ?
C20 N8 C21 125.81(17) . . ?
C19 N8 C21 129.37(16) . . ?
N1 C1 N2 130.0(2) . . ?
N1 C1 Cl1 115.74(17) . . ?
N2 C1 Cl1 114.26(16) . . ?
N2 C2 C3 121.8(2) . . ?
N2 C2 Cl2 116.83(15) . . ?
C3 C2 Cl2 121.33(17) . . ?
N3 C3 C2 134.5(2) . . ?
N3 C3 C5 110.96(17) . . ?
C2 C3 C5 114.44(19) . . ?
N3 C4 N4 114.99(18) . . ?
N1 C5 N4 127.62(18) . . ?
N1 C5 C3 126.56(18) . . ?
N4 C5 C3 105.80(17) . . ?
N4 C6 C7 109.92(16) . . ?
N4 C6 C15 109.90(16) . . ?
C7 C6 C15 112.96(17) . . ?
C8 C7 C12 119.95(19) . . ?
C8 C7 C6 119.08(18) . . ?
C12 C7 C6 120.96(19) . . ?
C9 C8 C7 120.9(2) . . ?
C8 C9 C10 119.6(2) . . ?
C11 C10 C9 119.6(2) . . ?
C10 C11 C12 122.0(2) . . ?
C11 C12 C7 117.9(2) . . ?
C11 C12 C13 120.03(19) . . ?
C7 C12 C13 122.09(19) . . ?
C12 C13 C14 112.94(18) . . ?
C15 C14 C13 109.21(19) . . ?
C14 C15 C6 111.11(19) . . ?
N5 C16 N6 130.19(19) . . ?
N5 C16 Cl3 115.39(17) . . ?
N6 C16 Cl3 114.42(15) . . ?
N6 C17 C18 121.5(2) . . ?
N6 C17 Cl4 117.10(16) . . ?
C18 C17 Cl4 121.41(17) . . ?
N7 C18 C17 134.3(2) . . ?
N7 C18 C20 110.82(17) . . ?
C17 C18 C20 114.87(19) . . ?
N7 C19 N8 115.20(18) . . ?
N5 C20 N8 126.97(18) . . ?
N5 C20 C18 126.62(18) . . ?
N8 C20 C18 106.41(17) . . ?
N8 C21 C30 109.70(17) . . ?
N8 C21 C22 110.17(17) . . ?
C30 C21 C22 112.60(17) . . ?
C23 C22 C27 119.99(19) . . ?
C23 C22 C21 119.31(18) . . ?
C27 C22 C21 120.69(19) . . ?
C24 C23 C22 121.3(2) . . ?
C23 C24 C25 119.2(2) . . ?
C26 C25 C24 120.0(2) . . ?
C25 C26 C27 121.8(2) . . ?
C26 C27 C22 117.7(2) . . ?
C26 C27 C28 120.06(19) . . ?
C22 C27 C28 122.24(19) . . ?
C27 C28 C29 113.30(18) . . ?
C30 C29 C28 110.18(19) . . ?
C29 C30 C21 110.71(19) . . ?
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 1.736(2) . ?
Cl2 C2 1.725(2) . ?
Cl3 C16 1.741(2) . ?
Cl4 C17 1.721(2) . ?
N1 C1 1.323(3) . ?
N1 C5 1.337(2) . ?
N2 C2 1.322(3) . ?
N2 C1 1.333(3) . ?
N3 C4 1.315(3) . ?
N3 C3 1.377(3) . ?
N4 C5 1.371(2) . ?
N4 C4 1.371(3) . ?
N4 C6 1.491(2) . ?
N5 C16 1.328(2) . ?
N5 C20 1.341(2) . ?
N6 C17 1.326(3) . ?
N6 C16 1.328(3) . ?
N7 C19 1.312(3) . ?
N7 C18 1.380(3) . ?
N8 C20 1.369(2) . ?
N8 C19 1.377(3) . ?
N8 C21 1.488(3) . ?
C2 C3 1.385(3) . ?
C3 C5 1.400(3) . ?
C6 C7 1.516(3) . ?
C6 C15 1.519(3) . ?
C7 C8 1.390(3) . ?
C7 C12 1.399(3) . ?
C8 C9 1.378(3) . ?
C9 C10 1.385(3) . ?
C10 C11 1.373(3) . ?
C11 C12 1.393(3) . ?
C12 C13 1.508(3) . ?
C13 C14 1.522(3) . ?
C14 C15 1.519(3) . ?
C17 C18 1.382(3) . ?
C18 C20 1.393(3) . ?
C21 C30 1.517(3) . ?
C21 C22 1.520(3) . ?
C22 C23 1.387(3) . ?
C22 C27 1.398(3) . ?
C23 C24 1.379(3) . ?
C24 C25 1.379(3) . ?
C25 C26 1.375(3) . ?
C26 C27 1.396(3) . ?
C27 C28 1.510(3) . ?
C28 C29 1.518(3) . ?
C29 C30 1.513(3) . ?
