Conformational Preferences of the Aglycon Moiety in Models and Analogs of GlcNAc-Asn Linkage: Crystal Structures and ab Initio Quantum Chemical Calculations of N-(β-d-Glycopyranosyl)haloacetamides
Mohamed Mohamed Naseer Ali; Udayanath Aich; Babu Varghese; Anne Imberty; Journal of the American Chemical Society 130 (2008) 8317–8325; doi:10.1021/ja800335m

data_4107940
_publ_contact_author_address
;
      Department of Chemistry
      IIT Madras
      Chennai 600 036
      INDIA
;
_publ_contact_author_email       loganath@iitm.ac.in
_publ_contact_author_fax         91-44-22570509
_publ_contact_author_name        ' Prof. D. Loganathan '
_publ_contact_author_phone       91-44-22574206
_publ_section_title
;
 Conformational Preferences of the Aglycon Moiety in Models and Analogs of
 GlcNAc-Asn Linkage: Crystal Structures and ab Initio Quantum Chemical
 Calculations of N-(\b-d-Glycopyranosyl)haloacetamides
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8317
_journal_page_last               8325
_journal_paper_doi               10.1021/ja800335m
_journal_volume                  130
_journal_year                    2008
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C10 H17 N2 O6 Cl.H2O'
_chemical_formula_sum            'C10 H19 Cl N2 O7'
_chemical_formula_weight         314.72
_chemical_melting_point          224
_chemical_name_common
'2-Acetamido-2-deoxyglucosylchloroacetamide monohydrate'
_chemical_name_systematic
;
 N-(2-Acetamido-2-deoxy-beta-D-glucopyranosyl)chloroacetamide monohydrate
;
_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                 91.27(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   4.919(3)
_cell_length_b                   7.856(8)
_cell_length_c                   18.784(7)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      14
_cell_measurement_theta_min      10
_cell_volume                     725.7(9)
_computing_cell_refinement       'CAD4 system software'
_computing_data_collection       'CAD4 system software'
_computing_data_reduction        'WinGX-Routine XCAD4'
_computing_molecular_graphics    'ORTEP3 (WinGX)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (WinGX)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       'non-profiled omega/2theta 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  0.0410
_diffrn_reflns_av_sigmaI/netI    0.0331
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            1537
_diffrn_reflns_theta_full        24.98
_diffrn_reflns_theta_max         24.98
_diffrn_reflns_theta_min         2.17
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  3600
_diffrn_standards_number         25
_exptl_absorpt_coefficient_mu    0.295
_exptl_absorpt_correction_T_max  0.9996
_exptl_absorpt_correction_T_min  0.9059
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details
;
North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351
Number of psi-scan sets used was   5
Theta correction was applied.
Averaged transmission function was used.
No Fourier smoothing was applied.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_description       needle
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.403
_refine_diff_density_min         -0.493
_refine_diff_density_rms         0.134
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.4(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.129
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         1365
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.128
_refine_ls_R_factor_all          0.0803
_refine_ls_R_factor_gt           0.0512
_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^)+(0.1433P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1377
_refine_ls_wR_factor_ref         0.1842
_reflns_number_gt                1148
_reflns_number_total             1365
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja800335m-file003_1.cif
_cod_data_source_block           a
_cod_original_sg_symbol_H-M      'P 21'
_cod_original_formula_sum        'C10 H19 N2 O7 Cl'
_cod_database_code               4107940