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_4107941
_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_formula_moiety         'C8 H14 N1 O6 Cl'
_chemical_formula_sum            'C8 H14 Cl N O6'
_chemical_formula_weight         255.65
_chemical_melting_point          175
_chemical_name_common            Mannosylchloroacetamide
_chemical_name_systematic
;
 N-(Beta-D-mannopyranosyl)chloroacetamide
;
_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                   6.3408(19)
_cell_length_b                   8.5671(8)
_cell_length_c                   19.352(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      15
_cell_measurement_theta_min      10
_cell_volume                     1051.2(4)
_computing_cell_refinement       'cad4 program'
_computing_data_collection       'cad4 program'
_computing_data_reduction        'xcad4 (wingx)'
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'cad4 diffractometer'
_diffrn_measurement_method       'omega twotheta'
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0188
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1105
_diffrn_reflns_theta_full        24.96
_diffrn_reflns_theta_max         24.96
_diffrn_reflns_theta_min         2.10
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  '1 hour'
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.378
_exptl_absorpt_correction_T_max  0.9937
_exptl_absorpt_correction_T_min  0.9154
_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   3
Theta correction was applied.
Averaged transmission function was used.
No Fourier smoothing was applied.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.615
_exptl_crystal_description       needle
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.425
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.11(13)
_refine_ls_extinction_coef       0.011(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         1105
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0398
_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^)+(0.0776P)^2^+0.2908P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1002
_refine_ls_wR_factor_ref         0.1078
_reflns_number_gt                997
_reflns_number_total             1105
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja800335m-file003_2.cif
_cod_data_source_block           b
_cod_original_formula_sum        'C8 H14 N1 O6 Cl'
_cod_database_code               4107941