Synthesis and evaluation of galacto-noeurostegine and its 2-deoxy analogue as glycosidase inhibitors.
Salamone, Stéphane; Clement, Lise L.; Viuff, Agnete H.; Andersen, Ole Juul; Jensen, Frank; Jensen, Henrik H.; Organic & biomolecular chemistry 13 (2015) 7979–7992; doi:10.1039/c5ob01062d

data_7154555
_publ_section_title
;
 Synthesis and evaluation of galacto-noeurostegine and its 2-deoxy
 analogue as glycosidase inhibitors.
;
_journal_issue                   29
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7979
_journal_page_last               7992
_journal_paper_doi               10.1039/c5ob01062d
_journal_volume                  13
_journal_year                    2015
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C43 H38 N4 O15'
_chemical_formula_sum            'C43 H38 N O15'
_chemical_formula_weight         808.74
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date
;
'Mon Jan 27 21:53:15 2014'
;
_audit_creation_method
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_audit_update_record
;
2014-10-24 deposited with the CCDC.
2015-06-26 downloaded from the CCDC.
;
_cell_angle_alpha                90.0
_cell_angle_beta                 91.013(3)
_cell_angle_gamma                90.0
_cell_formula_units_Z            2
_cell_length_a                   7.8734(2)
_cell_length_b                   17.4148(5)
_cell_length_c                   14.5347(4)
_cell_measurement_reflns_used    2961
_cell_measurement_temperature    125(30)
_cell_measurement_theta_max      27.1380
_cell_measurement_theta_min      2.7970
_cell_volume                     1992.59(9)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_diffrn_ambient_temperature      125(30)
_diffrn_detector_area_resol_mean 10.3590
_diffrn_measured_fraction_theta_full 0.908
_diffrn_measured_fraction_theta_max 0.884
_diffrn_measurement_details
;
  1 omega  -65.00   31.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -       10.6864  -38.0000 -180.0000 96

  2 omega   -7.00   32.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -       10.6864   57.0000  -30.0000 39
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0501858000
_diffrn_orient_matrix_UB_12      -0.0114982000
_diffrn_orient_matrix_UB_13      -0.0376410000
_diffrn_orient_matrix_UB_21      0.0651838000
_diffrn_orient_matrix_UB_22      0.0255403000
_diffrn_orient_matrix_UB_23      0.0147147000
_diffrn_orient_matrix_UB_31      0.0367672000
_diffrn_orient_matrix_UB_32      -0.0295657000
_diffrn_orient_matrix_UB_33      0.0273672000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_unetI/netI     0.0518
_diffrn_reflns_Laue_measured_fraction_full 0.908
_diffrn_reflns_Laue_measured_fraction_max 0.884
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7166
_diffrn_reflns_point_group_measured_fraction_full 0.721
_diffrn_reflns_point_group_measured_fraction_max 0.697
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.352
_diffrn_reflns_theta_min         2.338
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71929
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_F_000             846
_exptl_crystal_size_max          0.2042
_exptl_crystal_size_mid          0.1076
_exptl_crystal_size_min          0.0704
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 1542 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.2(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     559
_refine_ls_number_reflns         5679
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.130
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0454
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0390P)^2^+0.4966P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1004
_refine_ls_wR_factor_ref         0.1087
_reflns_Friedel_coverage         0.523
_reflns_Friedel_fraction_full    0.520
_reflns_Friedel_fraction_max     0.496
_reflns_number_gt                5041
_reflns_number_total             5679
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ob01062d2.cif
_cod_data_source_block           2014_01_27
_cod_depositor_comments
'Adding full bibliography for 7154555--7154556.cif.'
_cod_original_cell_volume        1992.58(9)
_cod_database_code               7154555
_shelxl_version_number           2013-2
_chemical_oxdiff_formula         'C25 H20 O4'
_cell_oxdiff_angle_alpha         89.985(4)
_cell_oxdiff_angle_beta          90.994(5)
_cell_oxdiff_angle_gamma         90.012(4)
_cell_oxdiff_length_a            7.8729(4)
_cell_oxdiff_length_b            17.4162(8)
_cell_oxdiff_length_c            14.5343(8)
_cell_oxdiff_measurement_reflns_used 2961
_cell_oxdiff_volume              1992.58(18)
_reflns_odcompleteness_completeness 88.47
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C6(H6), C17(H17), C23(H23), C30(H30)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C13(H13A,H13B), C25(H25A,H25B), C29(H29A,H29B),
 C41(H41A,H41B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C11(H11), C14(H14), C15(H15), C20(H20), C24(H24), C27(H27), C28(H28),
 C31(H31), C32(H32), C34(H34), C35(H35), C36(H36), C40(H40), C42(H42), C43(H43),
  C10(H10), C12(H12), C19(H19), C1B(H1B), C1C(H1C)
;