An Experimental and Theoretical Study on the Remarkable Influence of Protecting Groups on the Selectivity of Addition of Amines to Vinyl Sulfone-Modified Hex-2-enopyranosides
Rahul Bhattacharya; Manoj K. Kesharwani; Chinmoy Manna; Bishwajit Ganguly; Cheravakattu G. Suresh; Tanmaya Pathak; Journal of Organic Chemistry 75 (2010) 303–314; doi:10.1021/jo902046g

data_4025151
_publ_contact_author_address
'Chemistry Department, Indian Institute of Technology, Kharagpur 721302, India '
_publ_contact_author_email       tpathak@chem.iitkgp.ernet.in
_publ_contact_author_name        T.Pathak
_publ_section_title
;
 An Experimental and Theoretical Study on the Remarkable Influence of
 Protecting Groups on the Selectivity of Addition of Amines to Vinyl
 Sulfone-Modified Hex-2-enopyranosides
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              303
_journal_page_last               314
_journal_paper_doi               10.1021/jo902046g
_journal_volume                  75
_journal_year                    2010
_chemical_formula_moiety         'C37 H40 N O6.50 S'
_chemical_formula_sum            'C37 H40 N O6.5 S'
_chemical_formula_weight         634.76
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 94.826(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.7992(4)
_cell_length_b                   10.4914(5)
_cell_length_c                   18.5776(9)
_cell_measurement_reflns_used    790
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      21.52
_cell_measurement_theta_min      2.23
_cell_volume                     1903.14(15)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2000)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       '\w scans'
_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  0.0288
_diffrn_reflns_av_sigmaI/netI    0.0395
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7624
_diffrn_reflns_theta_full        23.28
_diffrn_reflns_theta_max         23.28
_diffrn_reflns_theta_min         2.09
_diffrn_standards_decay_%        <1
_diffrn_standards_interval_count n/a
_diffrn_standards_number         n/a
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  0.0136
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details   'SADABS  (Bruker-AXS, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.108
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             674
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.494
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.081
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.18(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    fixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     414
_refine_ls_number_reflns         5069
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0757
_refine_ls_R_factor_gt           0.0663
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1345P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1848
_refine_ls_wR_factor_ref         0.1920
_reflns_number_gt                4028
_reflns_number_total             5069
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo902046g_si_002.cif
_cod_data_source_block           s04a_t
_cod_depositor_comments
;
The following automatic conversions were performed:
data name '_publ_contact-author_address' replaced with
'_publ_contact_author_address' as specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_tags.lst'.

Automatic conversion script
Id: cif_correct_tags 4998 2017-03-02 13:24:31Z antanas 
;
_cod_original_cell_volume        1903.1(2)
_cod_original_sg_symbol_Hall     'P 21'
_cod_original_sg_symbol_H-M      'P 21'
_cod_original_formula_sum        'C37 H40 N O6.50 S'
_cod_database_code               4025151