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_1548478
_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            'C22 H27 N O3'
_chemical_formula_weight         353.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_cell_angle_alpha                90
_cell_angle_beta                 99.634(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   30.107(3)
_cell_length_b                   5.8007(5)
_cell_length_c                   11.5447(10)
_cell_measurement_reflns_used    8508
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.34
_cell_measurement_theta_min      2.43
_cell_volume                     1987.8(3)
_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 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            17456
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.481
_diffrn_reflns_theta_min         1.372
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6569
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Sheldrich , 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.181
_exptl_crystal_description       Block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.693
_exptl_crystal_size_mid          0.304
_exptl_crystal_size_min          0.229
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.116
_refine_diff_density_rms         0.026
_refine_ls_abs_structure_details
;
 Flack x determined using 1103 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.8(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         3660
_refine_ls_number_restraints     214
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0615
_refine_ls_R_factor_gt           0.0445
_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^)+(0.0555P)^2^+0.7747P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1123
_refine_ls_wR_factor_ref         0.1244
_reflns_Friedel_coverage         0.805
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                2792
_reflns_number_total             3660
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ncomms7903-s6.cif
_cod_data_source_block           mo_1MM014_half_0ma_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_original_cell_volume        1987.7(3)
_cod_database_code               1548478
_shelx_estimated_absorpt_t_min   0.948
_shelx_estimated_absorpt_t_max   0.982
_shelxl_version_number           2013-2
_shelx_res_checksum              75343
_shelx_hkl_checksum              81765