Direct synthesis of imino-C-nucleoside analogues and other biologically active iminosugars
Milan Bergeron-Brlek; Michael Meanwell; Robert Britton; Nature Communications 6 (2015) 6903–; doi:10.1038/ncomms7903

data_1548480
_publ_section_title
;
 Direct synthesis of imino-C-nucleoside analogues and other biologically
 active iminosugars
;
_journal_name_full               'Nature Communications'
_journal_page_first              6903
_journal_paper_doi               10.1038/ncomms7903
_journal_volume                  6
_journal_year                    2015
_chemical_absolute_configuration syn
_chemical_formula_sum            'C10 H16 N O3'
_chemical_formula_weight         198.24
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                83.648(3)
_cell_angle_beta                 81.203(3)
_cell_angle_gamma                83.714(3)
_cell_formula_units_Z            4
_cell_length_a                   5.0728(3)
_cell_length_b                   14.5938(7)
_cell_length_c                   15.1058(8)
_cell_measurement_reflns_used    6184
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      71.98
_cell_measurement_theta_min      2.97
_cell_volume                     1093.47(10)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_unetI/netI     0.0392
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            20511
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.847
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.312
_diffrn_reflns_theta_min         2.974
_exptl_absorpt_coefficient_mu    0.730
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6673
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Sheldrich , 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.204
_exptl_crystal_description       Block
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.466
_exptl_crystal_size_mid          0.101
_exptl_crystal_size_min          0.081
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details
;
 Flack x determined using 2536 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.11(10)
_refine_ls_extinction_coef       0.0060(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     510
_refine_ls_number_reflns         7335
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.112
_refine_ls_R_factor_all          0.0708
_refine_ls_R_factor_gt           0.0664
_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^)+(0.1378P)^2^+0.2592P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2111
_refine_ls_wR_factor_ref         0.2158
_reflns_Friedel_coverage         0.770
_reflns_Friedel_fraction_full    0.763
_reflns_Friedel_fraction_max     0.737
_reflns_number_gt                6552
_reflns_number_total             7335
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ncomms7903-s8.cif
_cod_data_source_block           cu_5MB032crystal2_0m_a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to the built-in table from CIF Core dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 5376 2017-05-30 11:51:03Z andrius 
;
_cod_database_code               1548480
_shelx_estimated_absorpt_t_min   0.727
_shelx_estimated_absorpt_t_max   0.943
_shelxl_version_number           2013-2
_shelx_res_checksum              57568
_shelx_hkl_checksum              50984