Stereoselective Synthesis of 1-Tuberculosinyl Adenosine; a Virulence Factor of Mycobacterium tuberculosis.
Buter, Jeffrey; Heijnen, Dorus; Wan, Ieng Chim; Bickelhaupt, F. Matthias; Young, David C.; Otten, Edwin; Moody, D. Branch; Minnaard, Adriaan J.; The Journal of organic chemistry 81 (2016) 6686–6696; doi:10.1021/acs.joc.6b01332

data_4037039
_publ_section_title
;
 Stereoselective Synthesis of 1-Tuberculosinyl Adenosine; a Virulence
 Factor of Mycobacterium tuberculosis.
;
_journal_issue                   15
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6686
_journal_page_last               6696
_journal_paper_doi               10.1021/acs.joc.6b01332
_journal_volume                  81
_journal_year                    2016
_chemical_absolute_configuration syn
_chemical_formula_sum            'C42 H66 N2 O6'
_chemical_formula_weight         694.96
_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_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 111.168(2)
_cell_angle_gamma                90
_cell_formula_units_Z            1
_cell_length_a                   10.1677(6)
_cell_length_b                   10.2037(5)
_cell_length_c                   10.2235(6)
_cell_measurement_reflns_used    9909
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.91
_cell_measurement_theta_min      2.92
_cell_volume                     989.10(10)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.993
_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  0.0332
_diffrn_reflns_av_unetI/netI     0.0397
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10524
_diffrn_reflns_point_group_measured_fraction_full 0.961
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.103
_diffrn_reflns_theta_min         3.536
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7114
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.167
_exptl_crystal_description       needle
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 1609 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         4173
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0404
_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^)+(0.0451P)^2^+0.2829P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0963
_refine_ls_wR_factor_ref         0.1007
_reflns_Friedel_coverage         0.824
_reflns_Friedel_fraction_full    0.925
_reflns_Friedel_fraction_max     0.918
_reflns_number_gt                3845
_reflns_number_total             4173
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b01332_si_002.cif
_cod_data_source_block           mo_molan355_0ma
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4037039
_shelx_estimated_absorpt_t_min   0.966
_shelx_estimated_absorpt_t_max   0.990
_shelxl_version_number           2014-3
_shelx_res_checksum              84043
_shelx_hkl_checksum              99189