Dual-face nucleoside scaffold featuring a stereogenic all-carbon quaternary center. Intramolecular silicon tethered group-transfer reaction.
Tambutet, Guillaume; Becerril-Jiménez, Fabiola; Dostie, Starr; Simard, Ryan; Prévost, Michel; Mochirian, Philippe; Guindon, Yvan; Organic letters 16 (2014) 5698–5701; doi:10.1021/ol502777r

data_1518047
_publ_section_title
;
 Dual-face nucleoside scaffold featuring a stereogenic all-carbon
 quaternary center. Intramolecular silicon tethered group-transfer
 reaction.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              5698
_journal_page_last               5701
_journal_paper_doi               10.1021/ol502777r
_journal_volume                  16
_journal_year                    2014
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'Cl, C11 H16 F2 N3 O4, C H4 O'
_chemical_formula_sum            'C12 H20 Cl F2 N3 O5'
_chemical_formula_weight         359.76
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2013-10-30
_audit_creation_method
;
Olex2 1.2
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_cell_angle_alpha                90
_cell_angle_beta                 91.8740(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.15770(10)
_cell_length_b                   16.9930(3)
_cell_length_c                   7.44300(10)
_cell_measurement_reflns_used    9573
_cell_measurement_temperature    100
_cell_measurement_theta_max      71.784
_cell_measurement_theta_min      5.949
_cell_volume                     778.40(2)
_computing_cell_refinement
;
SAINT (2013) V8.30C; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_collection
;
APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction
'SAINT (2013) V8.30C; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173.'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 8.3
_diffrn_detector_type            'Bruker APEX2 CCD'
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker Smart APEX'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Quazar MX Mirror Optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            10370
_diffrn_reflns_point_group_measured_fraction_full 0.954
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         71.778
_diffrn_reflns_theta_min         5.948
_diffrn_source                   'Microfocus Source'
_diffrn_source_target            Cu
_diffrn_source_type              'Incoatec I\mS High Brilliance Microsource'
_exptl_absorpt_coefficient_mu    2.664
_exptl_absorpt_correction_T_max  0.7535
_exptl_absorpt_correction_T_min  0.6316
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0938 before and 0.0557 after correction.
The Ratio of minimum to maximum transmission is 0.8382.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            ' colourless'
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.535
_exptl_crystal_description       FRAGMENT
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 1314 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.062(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         2867
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0230
_refine_ls_R_factor_gt           0.0229
_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^)+(0.0425P)^2^+0.0334P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0604
_refine_ls_wR_factor_ref         0.0605
_reflns_Friedel_coverage         0.867
_reflns_Friedel_fraction_full    0.927
_reflns_Friedel_fraction_max     0.903
_reflns_number_gt                2846
_reflns_number_total             2867
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol502777r_si_002.cif
_cod_data_source_block           guin80
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_absolute_configuration' value 'RMAD' changed to 'rmad'
according to
/home/saulius/struct/COD-crude-data--automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

'_diffrn_radiation_probe' value 'X-ray' changed to
'x-ray' according to
/home/saulius/struct/COD-crude-data--automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2827 2014-09-09 07:05:25Z andrius 

 Adding full bibliography for 1518047.cif.
;
_cod_database_code               1518047
_shelxl_version_number           2013-3
_shelx_estimated_absorpt_t_max   0.857
_shelx_estimated_absorpt_t_min   0.740
_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.a Ternary CH refined with riding coordinates:
 C7(H7), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C14(H14A,H14B,H14C)
;