Ring-Closing Metathesis and Glycosylation Reactions: Synthesis and Biophysical Studies of Polyether-Linked Carbohydrate-Based Macrocyclic Nucleosides.
Das, Soumendra Nath; Rana, Richa; Chatterjee, Sabyasachi; Suresh Kumar, Gopinatha; Mandal, Sukhendu B.; The Journal of organic chemistry 79 (2014) 9958–; doi:10.1021/jo501857k

data_4030106
_publ_section_title
;
 Ring-Closing Metathesis and Glycosylation Reactions: Synthesis and
 Biophysical Studies of Polyether-Linked Carbohydrate-Based Macrocyclic
 Nucleosides.
;
_journal_issue                   21
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9958
_journal_paper_doi               10.1021/jo501857k
_journal_volume                  79
_journal_year                    2014
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C20 H32 O9'
_chemical_formula_sum            'C20 H32 O9'
_chemical_formula_weight         416.45
_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             2014-08-19
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_cell_angle_alpha                90
_cell_angle_beta                 100.258(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.7618(11)
_cell_length_b                   28.360(4)
_cell_length_c                   8.9322(11)
_cell_measurement_reflns_used    9558
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.56
_cell_measurement_theta_min      2.32
_cell_volume                     2184.0(5)
_computing_cell_refinement       'SAINT v7.34A (Bruker, 200?)'
_computing_data_reduction        'SAINT v7.34A (Bruker, 200?)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.870
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_Laue_measured_fraction_full 0.870
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            26766
_diffrn_reflns_point_group_measured_fraction_full 0.837
_diffrn_reflns_point_group_measured_fraction_max 0.927
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         25.025
_diffrn_reflns_theta_min         1.436
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.820007
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2004/1 (Bruker,2004) was used for absorption correction.
R(int) was 0.3190 before and 0.0761 after correction.
The Ratio of minimum to maximum transmission is 0.8200.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_description       needle
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 2793 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     531
_refine_ls_number_reflns         7168
_refine_ls_number_restraints     31
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0392
_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^)+(0.0435P)^2^+0.4386P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0932
_refine_ls_wR_factor_ref         0.0978
_reflns_Friedel_coverage         0.884
_reflns_Friedel_fraction_full    0.802
_reflns_Friedel_fraction_max     0.890
_reflns_number_gt                6374
_reflns_number_total             7168
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo501857k_si_002.cif
_cod_data_source_block           sbm_sd_2s_3_aug13_0m
_cod_depositor_comments          'Adding full bibliography for 4030106.cif.'
_cod_database_code               4030106
_shelxl_version_number           2014/6
_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 C(H,H,H) groups
2. Rigid bond restraints
 C11, O9, C9
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C24, O11, C29
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C11 \\sim O9 \\sim C9: within 1.7A with sigma of 0.04 and sigma for terminal
atoms of 0.08
C24 \\sim O11 \\sim C29: within 1.7A with sigma of 0.04 and sigma for terminal
atoms of 0.08
4. Rigid body (RIGU) restrains
 C40, C30, C16
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14),
 C21(H21), C22(H22), C23(H23), C24(H24), C31(H31), C32(H32), C36(H36), C37(H37)
5.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B),
 C25(H25A,H25B), C26(H26A,H26B), C27(H27A,H27B), C28(H28A,H28B), C38(H38A,H38B),
  C39(H39A,H39B)
5.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C20(H20A,H20B,
 H20C), C30(H30A,H30B,H30C), C34(H34A,H34B,H34C), C35(H35A,H35B,H35C), C40(H40A,
 H40B,H40C)
;
_shelx_res_checksum              48288
_shelx_hkl_checksum              29817
_olex2_submission_special_instructions 'No special instructions were received'