Construction of cyclopentanol derivatives via three-component coupling of silyl glyoxylates, acetylides, and nitroalkenes.
Boyce, Gregory R.; Liu, Shubin; Johnson, Jeffrey S.; Organic letters 14 (2012) 652–655; doi:10.1021/ol2033527

data_1503597
_publ_section_title
;
 Construction of cyclopentanol derivatives via three-component coupling of
 silyl glyoxylates, acetylides, and nitroalkenes.
;
_journal_issue                   2
_journal_name_full               'Organic letters'
_journal_page_first              652
_journal_page_last               655
_journal_paper_doi               10.1021/ol2033527
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C26 H41 N O5 Si'
_chemical_formula_sum            'C26 H41 N O5 Si'
_chemical_formula_weight         475.69
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2011-12-29
_audit_creation_method
;
  Olex2 1.1
  (compiled Nov  1 2011 20:42:30, GUI svn.r3906)
;
_cell_angle_alpha                69.417(2)
_cell_angle_beta                 87.6310(10)
_cell_angle_gamma                73.582(2)
_cell_formula_units_Z            2
_cell_length_a                   9.6171(2)
_cell_length_b                   12.0518(3)
_cell_length_c                   12.9794(3)
_cell_measurement_reflns_used    3185
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      64.965
_cell_measurement_theta_min      4.090
_cell_volume                     1348.08(6)
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'CU K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_av_unetI/netI     0.0463
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9349
_diffrn_reflns_theta_full        65.73
_diffrn_reflns_theta_max         65.73
_diffrn_reflns_theta_min         4.09
_diffrn_source                   'sealed tube'
_diffrn_source_current           40.0
_diffrn_source_power             1.6
_diffrn_source_voltage           40.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.043
_exptl_absorpt_correction_T_max  0.9305
_exptl_absorpt_correction_T_min  0.7892
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
R(int) was 0.0545 before and 0.0451 after correction.
The Ratio of minimum to maximum transmission is 0.8481.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear ? colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.172
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.268
_exptl_crystal_size_mid          0.192
_exptl_crystal_size_min          0.152
_refine_diff_density_max         0.535
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     339
_refine_ls_number_reflns         4490
_refine_ls_number_restraints     63
_refine_ls_restrained_S_all      1.110
_refine_ls_R_factor_all          0.0700
_refine_ls_R_factor_gt           0.0592
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0934P)^2^+0.7550P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1534
_refine_ls_wR_factor_ref         0.1644
_reflns_number_gt                3647
_reflns_number_total             4490
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol2033527_si_003.cif
_cod_data_source_block           x1012004
_cod_original_cell_volume        1348.08(5)
_cod_database_code               1503597