Concise total synthesis of two marine natural nucleosides: trachycladines A and B.
Ding, Haixin; Li, Wei; Ruan, Zhizhong; Yang, Ruchun; Mao, Zhijie; Xiao, Qiang; Wu, Jun; Beilstein journal of organic chemistry 10 (2014) 1681–1685; doi:10.3762/bjoc.10.176

data_4029830
_publ_section_title
;
 Concise total synthesis of two marine natural nucleosides: trachycladines
 A and B.
;
_journal_name_full               'Beilstein journal of organic chemistry'
_journal_page_first              1681
_journal_page_last               1685
_journal_paper_doi               10.3762/bjoc.10.176
_journal_volume                  10
_journal_year                    2014
_chemical_formula_sum            'C14 H16 Cl2 O3'
_chemical_formula_weight         303.17
_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_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.2508(5)
_cell_length_b                   14.2668(12)
_cell_length_c                   19.7267(13)
_cell_measurement_reflns_used    1659
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.6773
_cell_measurement_theta_min      2.8497
_cell_volume                     1477.8(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_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  0.0356
_diffrn_reflns_av_sigmaI/netI    0.0409
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            8650
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.86
_exptl_absorpt_coefficient_mu    0.440
_exptl_absorpt_correction_T_max  0.9956
_exptl_absorpt_correction_T_min  0.9913
_exptl_absorpt_process_details   sadabs
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.791
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2612
_refine_ls_number_restraints     432
_refine_ls_restrained_S_all      0.881
_refine_ls_R_factor_all          0.0756
_refine_ls_R_factor_gt           0.0548
_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/[\s^2^(Fo^2^)+(0.1608P)^2^+0.9020P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1668
_refine_ls_wR_factor_ref         0.1984
_reflns_number_gt                1915
_reflns_number_total             2612
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1860-5397-10-176-S2.cif
_cod_data_source_block           liu20120430e
_cod_depositor_comments          'Adding full bibliography for 4029830.cif.'
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               4029830