#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/39/4023955.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_4023955
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           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 105.5220(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.8446(7)
_cell_length_b                   8.8930(5)
_cell_length_c                   12.8025(8)
_cell_measurement_reflns_used    7291
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.54
_cell_measurement_theta_min      2.73
_cell_volume                     1299.35(13)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_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  0.0321
_diffrn_reflns_av_sigmaI/netI    0.0446
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8183
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         2.08
_exptl_absorpt_coefficient_mu    0.493
_exptl_absorpt_correction_type   semi-empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.560
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2921
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0411
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0645P)²+0.2761P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1136
_refine_ls_wR_factor_ref         0.1175
_reflns_number_gt                2633
_reflns_number_total             2921
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo070515+si20070312_112551.cif
_cod_data_source_block           ms7ccd
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4023955
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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 -0.05824(4) 0.20547(5) 0.32248(3) 0.05359(16) Uani 1 1 d . . .
Cl2 Cl -0.31143(4) 0.59314(6) 0.46250(4) 0.05682(17) Uani 1 1 d . . .
N1 N -0.17503(11) 0.39586(15) 0.40873(10) 0.0391(3) Uani 1 1 d . . .
N2 N -0.13585(10) 0.46388(14) 0.59710(10) 0.0367(3) Uani 1 1 d . . .
N3 N 0.07785(12) 0.18756(17) 0.58074(11) 0.0455(3) Uani 1 1 d . . .
N4 N 0.02973(11) 0.32770(15) 0.70974(9) 0.0388(3) Uani 1 1 d . . .
C1 C -0.08563(13) 0.30032(17) 0.43017(11) 0.0366(3) Uani 1 1 d . . .
C2 C -0.19362(12) 0.46991(17) 0.49351(12) 0.0377(3) Uani 1 1 d . . .
C3 C -0.04802(12) 0.36526(16) 0.61397(10) 0.0335(3) Uani 1 1 d . . .
C4 C -0.01679(12) 0.27743(17) 0.53492(11) 0.0357(3) Uani 1 1 d . . .
C5 C 0.10179(15) 0.2213(2) 0.68369(13) 0.0462(4) Uani 1 1 d . . .
H5 H 0.1630 0.1766 0.7354 0.055 Uiso 1 1 calc R . .
C6 C 0.03498(13) 0.38981(18) 0.81720(11) 0.0402(3) Uani 1 1 d . . .
H6 H -0.0272 0.4651 0.8089 0.048 Uiso 1 1 calc R . .
C7 C 0.01690(15) 0.2689(2) 0.89792(12) 0.0478(4) Uani 1 1 d . . .
H7A H -0.0632 0.2693 0.9033 0.057 Uiso 1 1 calc R . .
H7B H 0.0355 0.1695 0.8761 0.057 Uiso 1 1 calc R . .
C8 C 0.10108(13) 0.31465(17) 1.00387(11) 0.0373(3) Uani 1 1 d . . .
C9 C 0.11063(15) 0.2574(2) 1.10661(12) 0.0456(4) Uani 1 1 d . . .
H9 H 0.0602 0.1821 1.1169 0.055 Uiso 1 1 calc R . .
C10 C 0.19668(16) 0.3141(2) 1.19409(12) 0.0486(4) Uani 1 1 d . . .
H10 H 0.2032 0.2778 1.2636 0.058 Uiso 1 1 calc R . .
C11 C 0.27240(16) 0.4243(2) 1.17788(13) 0.0499(4) Uani 1 1 d . . .
H11 H 0.3298 0.4613 1.2368 0.060 Uiso 1 1 calc R . .
C12 C 0.26422(15) 0.4808(2) 1.07505(13) 0.0471(4) Uani 1 1 d . . .
H12 H 0.3159 0.5544 1.0646 0.057 Uiso 1 1 calc R . .
C13 C 0.17730(13) 0.42515(17) 0.98809(11) 0.0376(3) Uani 1 1 d . . .
C14 C 0.15372(15) 0.46689(19) 0.87037(12) 0.0461(4) Uani 1 1 d . . .
H14A H 0.2149 0.4292 0.8399 0.055 Uiso 1 1 calc R . .
H14B H 0.1480 0.5751 0.8608 0.055 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 C2 116.28(12) . . ?
C2 N2 C3 111.20(12) . . ?
C5 N3 C4 103.26(13) . . ?
C3 N4 C5 105.33(12) . . ?
C3 N4 C6 126.84(13) . . ?
C5 N4 C6 127.82(12) . . ?
N1 C1 C4 121.63(14) . . ?
N1 C1 Cl1 117.34(11) . . ?
C4 C1 Cl1 121.03(12) . . ?
N2 C2 N1 129.90(13) . . ?
N2 C2 Cl2 115.11(12) . . ?
N1 C2 Cl2 114.99(10) . . ?
N2 C3 N4 128.09(13) . . ?
N2 C3 C4 126.43(12) . . ?
N4 C3 C4 105.49(12) . . ?
N3 C4 C1 134.46(15) . . ?
N3 C4 C3 110.98(12) . . ?
C1 C4 C3 114.55(13) . . ?
N3 C5 N4 114.94(13) . . ?
N4 C6 C7 112.71(13) . . ?
N4 C6 C14 112.59(13) . . ?
C7 C6 C14 106.62(12) . . ?
C8 C7 C6 103.72(13) . . ?
C13 C8 C9 120.52(14) . . ?
C13 C8 C7 111.09(13) . . ?
C9 C8 C7 128.36(15) . . ?
C8 C9 C10 119.13(16) . . ?
C11 C10 C9 120.10(15) . . ?
C10 C11 C12 121.06(15) . . ?
C11 C12 C13 118.66(16) . . ?
C8 C13 C12 120.52(14) . . ?
C8 C13 C14 111.57(12) . . ?
C12 C13 C14 127.88(15) . . ?
C13 C14 C6 103.56(13) . . ?
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 1.7196(16) . ?
Cl2 C2 1.7347(15) . ?
N1 C1 1.328(2) . ?
N1 C2 1.337(2) . ?
N2 C2 1.3206(18) . ?
N2 C3 1.3333(19) . ?
N3 C5 1.307(2) . ?
N3 C4 1.3738(19) . ?
N4 C3 1.3633(17) . ?
N4 C5 1.374(2) . ?
N4 C6 1.4683(18) . ?
C1 C4 1.3854(19) . ?
C3 C4 1.404(2) . ?
C6 C7 1.545(2) . ?
C6 C14 1.549(2) . ?
C7 C8 1.509(2) . ?
C8 C13 1.385(2) . ?
C8 C9 1.386(2) . ?
C9 C10 1.392(2) . ?
C10 C11 1.381(3) . ?
C11 C12 1.388(2) . ?
C12 C13 1.390(2) . ?
C13 C14 1.504(2) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 20565028
