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_1503596
_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         'C17 H21 N O5'
_chemical_formula_sum            'C17 H21 N O5'
_chemical_formula_weight         319.35
_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             2011-04-27
_audit_creation_method
;
  Olex2 1.1-beta
  (compiled Feb 15 2011 20:38:53, GUI svn.r3494)
;
_cell_angle_alpha                100.0550(10)
_cell_angle_beta                 102.351(2)
_cell_angle_gamma                115.5310(10)
_cell_formula_units_Z            2
_cell_length_a                   8.7703(2)
_cell_length_b                   9.2477(2)
_cell_length_c                   12.0469(3)
_cell_measurement_reflns_used    6295
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      65.86
_cell_measurement_theta_min      3.94
_cell_volume                     820.86(4)
_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  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'smtbx-flip (Bourhis, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9007
_diffrn_reflns_theta_full        66.29
_diffrn_reflns_theta_max         66.29
_diffrn_reflns_theta_min         3.94
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.788
_exptl_absorpt_correction_T_max  0.9521
_exptl_absorpt_correction_T_min  0.8062
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
 SADABS-2008/1 (Bruker,2008) was used for absorption correction.
 R(int) was 0.0463 before and 0.0383 after correction.
 The Ratio of minimum to maximum transmission is 0.846759794139.
 The \l/2 correction factor is 0.0015
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.303
_exptl_crystal_size_mid          0.253
_exptl_crystal_size_min          0.082
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         2789
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0381
_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^)+(0.0690P)^2^+0.2070P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1039
_refine_ls_wR_factor_ref         0.1073
_reflns_number_gt                2539
_reflns_number_total             2789
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol2033527_si_001.cif
_cod_data_source_block           x1104027
_cod_original_cell_volume        820.86(3)
_cod_database_code               1503596