Ex Post Glycoconjugation of Phthalocyanines
Herwig Josef Berthold; Stephan Franke; Joachim Thiem; Theo Schotten; Hoffmann, Frank; Journal of Organic Chemistry 75 (2010) 3859–3862; doi:10.1021/jo100362n

data_4025443
_publ_contact_author_address
;University of Hamburg
Department of Chemistry
Martin-Luther-King-Platz 6
20146 Hamburg
Germany
;
_publ_contact_author_email       berthold@chemie.uni-hamburg.de
_publ_contact_author_fax         49(40)42838x4325
_publ_contact_author_name        'Herwig BERTHOLD'
_publ_contact_author_phone       49(40)34832205
_publ_section_title
;
 Ex Post Glycoconjugation of Phthalocyanines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3859
_journal_page_last               3862
_journal_paper_doi               10.1021/jo100362n
_journal_volume                  75
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C14 H21 N O9'
_chemical_formula_sum            'C14 H21 N O9'
_chemical_formula_weight         347.32
_chemical_melting_point          384
_chemical_name_common
2,3,4,6-tetra-<i>O</i>-acetyl-<i>\b</i>-D-glucopyranosyl_amine
_chemical_name_systematic
'2,3,4,6-tetra-<i>O</i>-acetyl-<i>\b</i>-D-glucopyranosyl amine'
_chemical_properties_physical    moisture-sensitive
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_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
_audit_update_record
;
2010-04-14 # Formatted by publCIF
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.6096(10)
_cell_length_b                   13.645(2)
_cell_length_c                   23.142(4)
_cell_measurement_reflns_used    1478
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.0
_cell_measurement_theta_min      1.2
_cell_volume                     1771.4(5)
_computing_cell_refinement       'SAINT (Bruker AXS, 1998)'
_computing_data_collection       'SMART (Bruker AXS, 1998)'
_computing_data_reduction        'SAINT (Bruker AXS, 1998)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker Smart APEX CCD area detector'
_diffrn_measurement_method       omega-scan
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0862
_diffrn_reflns_av_sigmaI/netI    0.0807
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            20903
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.73
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.9967
_exptl_absorpt_correction_T_min  0.9471
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 1998)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             736
_exptl_crystal_recrystallization_method 'ethyl acetate'
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.727
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         2354
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.727
_refine_ls_R_factor_all          0.0749
_refine_ls_R_factor_gt           0.0370
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0358P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0620
_refine_ls_wR_factor_ref         0.0712
_reflns_number_gt                1463
_reflns_number_total             2354
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo100362n_si_002.cif
_cod_data_source_block           0467se
_cod_database_code               4025443