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_7154556
_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 rm
_chemical_formula_moiety         'C29 H34 O5'
_chemical_formula_sum            'C29 H34 O5'
_chemical_formula_weight         462.56
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_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
_audit_creation_date             2014-08-21
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:59:47, GUI svn.r4466)
;
_audit_update_record
;
2014-10-24 deposited with the CCDC.
2015-06-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.3233(6)
_cell_length_b                   10.2871(8)
_cell_length_c                   26.846(2)
_cell_measurement_reflns_used    28015
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      29.0240
_cell_measurement_theta_min      2.5330
_cell_volume                     2574.8(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3590
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.9987
_diffrn_measured_fraction_theta_max 0.9470
_diffrn_measurement_details
;
  1 omega  -94.00    5.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.6633  -38.0000  -30.0000 99

  2 omega  -44.00   55.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.6633   38.0000  150.0000 99

  3 omega  -57.00   29.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.6633   91.0000   16.3376 86

  4 omega  -61.00   60.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.6633   19.0000  -30.0000 121

  5 omega  -86.00  -11.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.6633  141.0000 -121.0000 75

  6 omega  -76.00   -2.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.6633  125.0000  133.7571 74

  7 omega   35.00  107.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       18.4133  178.0000 -180.0000 72

  8 omega  -10.00   91.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       18.4133   57.0000   30.0000 101

  9 omega  -91.00  -14.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.6633  148.0000    2.9240 77

 10 omega  -91.00  -14.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.6633  148.0000  -79.0724 77

 11 omega  -87.00  -12.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.6633  143.0000 -168.0459 75

 12 omega -108.00  -35.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.6633 -178.0000 -120.0000 73

 13 omega   11.00   84.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       18.4133 -141.0000 -178.0000 73

 14 omega  -70.00  107.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       18.4133    0.0000 -180.0000 177

 15 omega   -6.00   93.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       18.4133   38.0000  -60.0000 99
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0108851000
_diffrn_orient_matrix_UB_12      -0.0335793000
_diffrn_orient_matrix_UB_13      -0.0226460000
_diffrn_orient_matrix_UB_21      0.0295539000
_diffrn_orient_matrix_UB_22      0.0533631000
_diffrn_orient_matrix_UB_23      -0.0131623000
_diffrn_orient_matrix_UB_31      0.0697178000
_diffrn_orient_matrix_UB_32      -0.0279215000
_diffrn_orient_matrix_UB_33      0.0020489000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0740
_diffrn_reflns_av_unetI/netI     0.0481
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            114218
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.074
_diffrn_reflns_theta_min         2.312
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86320
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.193
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Flack x determined using 2409 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.0(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         9266
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0955
_refine_ls_R_factor_gt           0.0492
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0456P)^2^+0.7593P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1052
_refine_ls_wR_factor_ref         0.1273
_reflns_Friedel_coverage         0.773
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.932
_reflns_number_gt                6450
_reflns_number_total             9266
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ob01062d2.cif
_cod_data_source_block           mikkel17072014_100k
_cod_depositor_comments
'Adding full bibliography for 7154555--7154556.cif.'
_cod_database_code               7154556
_chemical_oxdiff_formula         O5C29H34
_reflns_odcompleteness_completeness 99.87
_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
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5), C7(H7), C10(H10), C15(H15), C21(H21)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C11(H11A,H11B), C12(H12A,H12B), C14(H14A,H14B), C20(H20A,H20B),
 C25(H25A,H25B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C16(H16), C17(H17), C18(H18), C19(H19), C23(H23), C24(H24), C26(H26),
 C27(H27), C28(H28), C29(H29), C30(H30), C31(H31), C32(H32), C33(H33)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1A), O8(H8)
;
_shelx_res_checksum              98628
_shelxl_version_number           2013-4