Divergent synthesis of new α-glucosidase inhibitors obtained through a vinyl Grignard-mediated carbocyclisation.
Knudsen, Ida M. B.; Hedberg, Christinne; Ladefoged, Lucy Kate; Ide, Daisuke; Brinkø, Anne; Eikeland, Espen Z.; Kato, Atsushi; Jensen, Henrik H.; Organic & biomolecular chemistry 16 (2018) 6250–6261; doi:10.1039/c8ob01433g

data_7156366
_publ_section_title
;
 Divergent synthesis of new \a-glucosidase inhibitors obtained through a
 vinyl Grignard-mediated carbocyclisation.
;
_journal_issue                   34
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6250
_journal_page_last               6261
_journal_paper_doi               10.1039/c8ob01433g
_journal_volume                  16
_journal_year                    2018
_chemical_formula_moiety         'C44 H43 N3 O8'
_chemical_formula_sum            'C44 H43 N3 O8'
_chemical_formula_weight         741.81
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-09-05
_audit_creation_method
;
Olex2 1.2
(compiled 2016.08.25 svn.r3337 for OlexSys, GUI svn.r5221)
;
_audit_update_record
;
2018-05-15 deposited with the CCDC.
2018-08-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.0654(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.67340(19)
_cell_length_b                   10.41568(13)
_cell_length_c                   27.6271(4)
_cell_measurement_reflns_used    25889
_cell_measurement_temperature    100.01(13)
_cell_measurement_theta_max      27.8570
_cell_measurement_theta_min      2.4860
_cell_volume                     3832.73(9)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(13)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3590
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -25.00 126.00   1.00   60.00    --   21.23  77.00-120.00  151
  2  \w    -25.00 126.00   1.00   60.00    --   21.23  77.00  30.00  151
  3  \w    -25.00 126.00   1.00   60.00    --   21.23  77.00 -60.00  151
  4  \w    -68.00  83.00   1.00   60.00    --  -22.02  77.00 150.00  151
  5  \w     62.00 120.00   1.00   60.00    --   21.23 144.00 104.00   58
  6  \w     34.00  71.00   1.00   60.00    --   21.23-178.00 -60.00   37
  7  \w     35.00 126.00   1.00   60.00    --   21.23 178.00 150.00   91
  8  \w    -31.00 117.00   1.00   60.00    --   21.23  38.00-150.00  148
  9  \w   -120.00 -62.00   1.00   60.00    --  -22.02-144.00  51.00   58
 10  \w    -20.00  31.00   1.00   60.00    --  -22.02 -99.00  60.00   51
 11  \w    -68.00  83.00   1.00   60.00    --  -22.02  77.00 -60.00  151
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0509067000
_diffrn_orient_matrix_UB_12      0.0199673000
_diffrn_orient_matrix_UB_13      -0.0055798000
_diffrn_orient_matrix_UB_21      -0.0003001000
_diffrn_orient_matrix_UB_22      -0.0001535000
_diffrn_orient_matrix_UB_23      -0.0257122000
_diffrn_orient_matrix_UB_31      -0.0155959000
_diffrn_orient_matrix_UB_32      -0.0651028000
_diffrn_orient_matrix_UB_33      -0.0016392000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0484
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            78629
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         2.270
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.375
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43b (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_description       block
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.437
_exptl_crystal_size_mid          0.271
_exptl_crystal_size_min          0.101
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 5681 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     993
_refine_ls_number_reflns         15663
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0381
_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^)+(0.0362P)^2^+0.5644P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0832
_refine_ls_wR_factor_ref         0.0889
_reflns_Friedel_coverage         0.892
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                13721
_reflns_number_total             15663
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob01433g2.cif
_cod_data_source_block           C44H43N3O8
_cod_depositor_comments          'Adding full bibliography for 7156366.cif.'
_cod_database_code               7156366
_chemical_oxdiff_formula         C43H41O8N3
_reflns_odcompleteness_completeness 99.90
_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:
 C1B(H1B), C5A(H5A), C6A(H6A), C4B(H4B), C2B(H2B), C4A(H4A), C2A(H2A),
 C5B(H5B), C1A(H1A), C6B(H6B)
2.b Secondary CH2 refined with riding coordinates:
 C16B(H16A,H16B), C37A(H37A,H37C), C8A(H8AA,H8AB), C7B(H7BA,H7BB), C7A(H7AA,
 H7AB), C16A(H16C,H16D), C38B(H38A,H38B), C8B(H8BA,H8BB), C31B(H31A,H31B),
 C24B(H24A,H24B), C23A(H23A,H23C), C30A(H30A,H30C)
2.c Aromatic/amide H refined with riding coordinates:
 C23B(H23B), C37B(H37B), C28B(H28B), C19B(H19B), C22B(H22B), C40A(H40A),
 C36B(H36B), C29B(H29B), C35B(H35B), C33B(H33B), C18A(H18A), C29A(H29A),
 C22A(H22A), C26B(H26B), C43A(H43A), C27B(H27B), C44B(H44B), C11B(H11B),
 C15A(H15A), C32A(H32A), C44A(H44A), C21B(H21B), C20B(H20B), C19A(H19A),
 C36A(H36A), C21A(H21A), C40B(H40B), C33A(H33A), C42A(H42A), C35A(H35A),
 C41A(H41A), C30B(H30B), C25A(H25A), C28A(H28A), C41B(H41B), C42B(H42B),
 C20A(H20A), C43B(H43B), C15B(H15B), C27A(H27A), C11A(H11A), C34A(H34A),
 C34B(H34B), C14A(H14A), C13B(H13B), C12B(H12B), C12A(H12A), C14B(H14B),
 C26A(H26A), C13A(H13A)
2.d Idealised tetrahedral OH refined as rotating group:
 O3B(H3B), O3A(H3A)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.634
_oxdiff_exptl_absorpt_empirical_full_min 0.697