#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/54/4025443.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4025443
loop_
_publ_author_name
'Herwig Josef Berthold'
'Stephan Franke'
'Joachim Thiem'
'Theo Schotten'
'Hoffmann, Frank'
_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-O-acetyl-β-D-glucopyranosyl_amine
_chemical_name_systematic
'2,3,4,6-tetra-O-acetyl-β-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/[σ²(Fo²)+(0.0358P)²+0.0000P] where P=(Fo²+2Fc²)/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
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O5 O 0.3206(3) 0.23688(12) 0.43445(7) 0.0272(4) Uani 1 1 d . . .
O21 O 0.5578(3) 0.48770(11) 0.42104(7) 0.0299(5) Uani 1 1 d . . .
O22 O 0.8723(4) 0.48330(13) 0.48216(8) 0.0472(6) Uani 1 1 d . . .
O31 O 0.7849(3) 0.38309(12) 0.32617(7) 0.0289(5) Uani 1 1 d . . .
O32 O 0.6081(3) 0.47287(15) 0.25571(8) 0.0460(6) Uani 1 1 d . . .
O41 O 0.4720(3) 0.23361(11) 0.28043(7) 0.0308(5) Uani 1 1 d . . .
O42 O 0.8420(4) 0.16870(16) 0.26754(9) 0.0519(6) Uani 1 1 d . . .
O61 O 0.4732(3) 0.05611(11) 0.38713(7) 0.0287(4) Uani 1 1 d . . .
O62 O 0.2805(3) -0.08950(13) 0.38743(8) 0.0390(5) Uani 1 1 d . . .
N1 N 0.3460(5) 0.36095(17) 0.50609(10) 0.0313(6) Uani 1 1 d . . .
H11 H 0.194(5) 0.3462(18) 0.5236(11) 0.042(9) Uiso 1 1 d . . .
H12 H 0.458(6) 0.328(2) 0.5262(12) 0.058(11) Uiso 1 1 d . . .
C2 C 0.5595(5) 0.38126(16) 0.41573(10) 0.0246(6) Uani 1 1 d . . .
H2 H 0.7056 0.3533 0.4342 0.029 Uiso 1 1 calc R . .
C4 C 0.5148(5) 0.24894(17) 0.34168(10) 0.0260(6) Uani 1 1 d . . .
H4 H 0.6579 0.2109 0.3543 0.031 Uiso 1 1 calc R . .
C1 C 0.3351(5) 0.34303(17) 0.44576(10) 0.0270(6) Uani 1 1 d . . .
H1 H 0.1917 0.3763 0.4292 0.032 Uiso 1 1 calc R . .
C5 C 0.2941(5) 0.21327(17) 0.37393(10) 0.0259(6) Uani 1 1 d . . .
H5 H 0.1509 0.2481 0.3584 0.031 Uiso 1 1 calc R . .
C3 C 0.5563(5) 0.35854(17) 0.35140(10) 0.0246(6) Uani 1 1 d . . .
H3 H 0.4273 0.3971 0.3321 0.029 Uiso 1 1 calc R . .
C6 C 0.2549(5) 0.10376(18) 0.36886(11) 0.0295(7) Uani 1 1 d . . .
H61 H 0.1205 0.0831 0.3938 0.035 Uiso 1 1 calc R . .
H62 H 0.2172 0.0860 0.3284 0.035 Uiso 1 1 calc R . .
C21 C 0.7180(5) 0.52899(19) 0.45763(11) 0.0317(7) Uani 1 1 d . . .
C41 C 0.6523(6) 0.19300(19) 0.24817(12) 0.0367(7) Uani 1 1 d . . .
C61 C 0.4611(5) -0.04195(19) 0.39580(11) 0.0307(7) Uani 1 1 d . . .
C31 C 0.7847(5) 0.43387(19) 0.27517(11) 0.0311(7) Uani 1 1 d . . .
C62 C 0.6927(5) -0.08232(19) 0.41607(12) 0.0386(8) Uani 1 1 d . . .
H621 H 0.6737 -0.1520 0.4253 0.058 Uiso 1 1 calc R . .
H622 H 0.7445 -0.0468 0.4507 0.058 Uiso 1 1 calc R . .
H623 H 0.8125 -0.0748 0.3856 0.058 Uiso 1 1 calc R . .
C22 C 0.6774(6) 0.63772(18) 0.46325(12) 0.0469(9) Uani 1 1 d . . .
H221 H 0.7000 0.6575 0.5036 0.070 Uiso 1 1 calc R . .
H222 H 0.5145 0.6536 0.4511 0.070 Uiso 1 1 calc R . .
H223 H 0.7912 0.6729 0.4387 0.070 Uiso 1 1 calc R . .
C42 C 0.5774(6) 0.1855(2) 0.18576(11) 0.0537(10) Uani 1 1 d . . .
H421 H 0.6284 0.2444 0.1650 0.080 Uiso 1 1 calc R . .
H422 H 0.4036 0.1794 0.1835 0.080 Uiso 1 1 calc R . .
H423 H 0.6517 0.1277 0.1682 0.080 Uiso 1 1 calc R . .
C32 C 1.0249(5) 0.4317(2) 0.24786(12) 0.0428(8) Uani 1 1 d . . .
H321 H 1.0103 0.4470 0.2066 0.064 Uiso 1 1 calc R . .
H322 H 1.0948 0.3664 0.2525 0.064 Uiso 1 1 calc R . .
H323 H 1.1278 0.4805 0.2665 0.064 Uiso 1 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O5 C1 113.38(17) . . ?
C21 O21 C2 117.5(2) . . ?
C31 O31 C3 117.6(2) . . ?
C41 O41 C4 117.8(2) . . ?
C61 O61 C6 116.4(2) . . ?
C1 N1 H11 109.9(16) . . ?
C1 N1 H12 116.6(18) . . ?
H11 N1 H12 107(2) . . ?
O21 C2 C3 106.59(18) . . ?
O21 C2 C1 107.2(2) . . ?
C3 C2 C1 111.4(2) . . ?
O21 C2 H2 110.5 . . ?
C3 C2 H2 110.5 . . ?
C1 C2 H2 110.5 . . ?
O41 C4 C5 107.3(2) . . ?
O41 C4 C3 108.02(18) . . ?
C5 C4 C3 111.3(2) . . ?
O41 C4 H4 110.0 . . ?
C5 C4 H4 110.0 . . ?
C3 C4 H4 110.0 . . ?
N1 C1 O5 110.3(2) . . ?
N1 C1 C2 110.7(2) . . ?
O5 C1 C2 107.4(2) . . ?
N1 C1 H1 109.5 . . ?
O5 C1 H1 109.5 . . ?
C2 C1 H1 109.5 . . ?
O5 C5 C6 108.1(2) . . ?
O5 C5 C4 108.6(2) . . ?
C6 C5 C4 113.2(2) . . ?
O5 C5 H5 108.9 . . ?
C6 C5 H5 108.9 . . ?
C4 C5 H5 108.9 . . ?
O31 C3 C2 109.7(2) . . ?
O31 C3 C4 107.5(2) . . ?
C2 C3 C4 110.18(19) . . ?
O31 C3 H3 109.8 . . ?
C2 C3 H3 109.8 . . ?
C4 C3 H3 109.8 . . ?
O61 C6 C5 107.3(2) . . ?
O61 C6 H61 110.3 . . ?
C5 C6 H61 110.3 . . ?
O61 C6 H62 110.3 . . ?
C5 C6 H62 110.3 . . ?
H61 C6 H62 108.5 . . ?
O22 C21 O21 123.6(2) . . ?
O22 C21 C22 125.1(3) . . ?
O21 C21 C22 111.3(3) . . ?
O42 C41 O41 124.1(3) . . ?
O42 C41 C42 125.8(3) . . ?
O41 C41 C42 110.1(3) . . ?
O62 C61 O61 122.9(3) . . ?
O62 C61 C62 125.4(2) . . ?
O61 C61 C62 111.7(2) . . ?
O32 C31 O31 123.0(3) . . ?
O32 C31 C32 126.2(2) . . ?
O31 C31 C32 110.8(2) . . ?
C61 C62 H621 109.5 . . ?
C61 C62 H622 109.5 . . ?
H621 C62 H622 109.5 . . ?
C61 C62 H623 109.5 . . ?
H621 C62 H623 109.5 . . ?
H622 C62 H623 109.5 . . ?
C21 C22 H221 109.5 . . ?
C21 C22 H222 109.5 . . ?
H221 C22 H222 109.5 . . ?
C21 C22 H223 109.5 . . ?
H221 C22 H223 109.5 . . ?
H222 C22 H223 109.5 . . ?
C41 C42 H421 109.5 . . ?
C41 C42 H422 109.5 . . ?
H421 C42 H422 109.5 . . ?
C41 C42 H423 109.5 . . ?
H421 C42 H423 109.5 . . ?
H422 C42 H423 109.5 . . ?
C31 C32 H321 109.5 . . ?
C31 C32 H322 109.5 . . ?
H321 C32 H322 109.5 . . ?
C31 C32 H323 109.5 . . ?
H321 C32 H323 109.5 . . ?
H322 C32 H323 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O5 C5 1.445(3) . ?
O5 C1 1.474(3) . ?
O21 C21 1.357(3) . ?
O21 C2 1.458(3) . ?
O22 C21 1.209(3) . ?
O31 C31 1.368(3) . ?
O31 C3 1.448(3) . ?
O32 C31 1.211(3) . ?
O41 C41 1.373(3) . ?
O41 C4 1.453(3) . ?
O42 C41 1.201(3) . ?
O61 C61 1.355(3) . ?
O61 C6 1.449(3) . ?
O62 C61 1.219(3) . ?
N1 C1 1.419(3) . ?
N1 H11 0.96(3) . ?
N1 H12 0.90(3) . ?
C2 C3 1.521(3) . ?
C2 C1 1.529(4) . ?
C2 H2 1.0000 . ?
C4 C5 1.525(3) . ?
C4 C3 1.530(3) . ?
C4 H4 1.0000 . ?
C1 H1 1.0000 . ?
C5 C6 1.515(3) . ?
C5 H5 1.0000 . ?
C3 H3 1.0000 . ?
C6 H61 0.9900 . ?
C6 H62 0.9900 . ?
C21 C22 1.507(3) . ?
C41 C42 1.507(4) . ?
C61 C62 1.487(4) . ?
C31 C32 1.489(4) . ?
C62 H621 0.9800 . ?
C62 H622 0.9800 . ?
C62 H623 0.9800 . ?
C22 H221 0.9800 . ?
C22 H222 0.9800 . ?
C22 H223 0.9800 . ?
C42 H421 0.9800 . ?
C42 H422 0.9800 . ?
C42 H423 0.9800 . ?
C32 H321 0.9800 . ?
C32 H322 0.9800 . ?
C32 H323 0.9800 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C21 O21 C2 C3 -132.2(2) . . . . ?
C21 O21 C2 C1 108.3(2) . . . . ?
C41 O41 C4 C5 -134.9(2) . . . . ?
C41 O41 C4 C3 105.0(2) . . . . ?
C5 O5 C1 N1 176.4(2) . . . . ?
C5 O5 C1 C2 -62.9(3) . . . . ?
O21 C2 C1 N1 -66.3(3) . . . . ?
C3 C2 C1 N1 177.4(2) . . . . ?
O21 C2 C1 O5 173.24(18) . . . . ?
C3 C2 C1 O5 56.9(3) . . . . ?
C1 O5 C5 C6 -174.0(2) . . . . ?
C1 O5 C5 C4 62.8(3) . . . . ?
O41 C4 C5 O5 -174.11(18) . . . . ?
C3 C4 C5 O5 -56.1(3) . . . . ?
O41 C4 C5 C6 65.9(3) . . . . ?
C3 C4 C5 C6 -176.2(2) . . . . ?
C31 O31 C3 C2 -134.5(2) . . . . ?
C31 O31 C3 C4 105.7(2) . . . . ?
O21 C2 C3 O31 71.5(3) . . . . ?
C1 C2 C3 O31 -171.86(18) . . . . ?
O21 C2 C3 C4 -170.3(2) . . . . ?
C1 C2 C3 C4 -53.7(3) . . . . ?
O41 C4 C3 O31 -70.2(3) . . . . ?
C5 C4 C3 O31 172.24(18) . . . . ?
O41 C4 C3 C2 170.3(2) . . . . ?
C5 C4 C3 C2 52.7(3) . . . . ?
C61 O61 C6 C5 168.4(2) . . . . ?
O5 C5 C6 O61 -66.5(3) . . . . ?
C4 C5 C6 O61 53.9(3) . . . . ?
C2 O21 C21 O22 6.1(4) . . . . ?
C2 O21 C21 C22 -174.0(2) . . . . ?
C4 O41 C41 O42 0.6(4) . . . . ?
C4 O41 C41 C42 -178.4(2) . . . . ?
C6 O61 C61 O62 2.0(4) . . . . ?
C6 O61 C61 C62 -178.3(2) . . . . ?
C3 O31 C31 O32 12.8(4) . . . . ?
C3 O31 C31 C32 -165.9(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9998852
