New method for chloroamidation of olefins. Application in the synthesis of N-glycopeptides and anticancer agents.
Rawal, Girish K.; Kumar, Amit; Tawar, Urmila; Vankar, Yashwant D.; Organic letters 9 (2007) 5171–5174; doi:10.1021/ol702097q

data_1505584
_publ_section_title
;
 New method for chloroamidation of olefins. Application in the synthesis
 of N-glycopeptides and anticancer agents.
;
_journal_issue                   25
_journal_name_full               'Organic letters'
_journal_page_first              5171
_journal_page_last               5174
_journal_paper_doi               10.1021/ol702097q
_journal_volume                  9
_journal_year                    2007
_chemical_formula_moiety         'C14 H20 Cl N O8'
_chemical_formula_sum            'C14 H20 Cl N O8'
_chemical_formula_weight         365.76
_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                   8.1991(7)
_cell_length_b                   8.7860(8)
_cell_length_c                   23.326(2)
_cell_measurement_temperature    293(2)
_cell_volume                     1680.3(3)
_computing_cell_refinement       'Bruker SMART v5.628'
_computing_data_collection       'Bruker SMART v5.628'
_computing_data_reduction        'Bruker SAINT+ v6.45'
_computing_molecular_graphics    ORTEP
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR 97'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0379
_diffrn_reflns_av_sigmaI/netI    0.0480
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            11142
_diffrn_reflns_theta_full        28.30
_diffrn_reflns_theta_max         28.30
_diffrn_reflns_theta_min         2.48
_exptl_absorpt_coefficient_mu    0.269
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.420
_refine_diff_density_min         -0.221
_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   -0.05(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         4102
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0468
_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/[\s^2^(Fo^2^)+(0.0485P)^2^+0.1683P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0992
_refine_ls_wR_factor_ref         0.1020
_reflns_number_gt                3703
_reflns_number_total             4102
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol702097q-file004.cif
_cod_data_source_block           13jundm
_cod_original_cell_volume        1680.4(3)
_cod_database_code               1505584