Total synthesis of (±)-cylindricine C.
Lapointe, Guillaume; Schenk, Kurt; Renaud, Philippe; Organic letters 13 (2011) 4774–4777; doi:10.1021/ol201745s

data_1502381
_publ_section_title
;
 Total synthesis of (+-)-cylindricine C.
;
_journal_issue                   18
_journal_name_full               'Organic letters'
_journal_page_first              4774
_journal_page_last               4777
_journal_paper_doi               10.1021/ol201745s
_journal_volume                  13
_journal_year                    2011
_chemical_formula_moiety         'C27 H51 N O3 Si'
_chemical_formula_sum            'C27 H51 N O3 Si'
_chemical_formula_weight         465.78
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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             '6th April 2009'
_audit_creation_method           'SHELXL-97 & Stoe X-Red'
_cell_angle_alpha                92.681(10)
_cell_angle_beta                 108.486(9)
_cell_angle_gamma                110.798(9)
_cell_formula_units_Z            2
_cell_length_a                   10.2256(12)
_cell_length_b                   10.8683(13)
_cell_length_c                   15.1033(18)
_cell_measurement_reflns_used    38755
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      29.54
_cell_measurement_theta_min      2.04
_cell_volume                     1463.9(3)
_computing_cell_refinement       'X-Area (Stoe & CIe, 2008)'
_computing_data_collection       'X-Area (Stoe & CIe, 2008)'
_computing_data_reduction        'X-Area (Stoe & CIe, 2008)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1995)'
_computing_publication_material  'SHELXTL (Bruker, 1995)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      292(2)
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_detector_type            STOE
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_details      ' 540 frames, detector distance = 100 mm'
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_collimation    '0.8 mm diameter'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0499
_diffrn_reflns_av_sigmaI/netI    0.0352
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            39778
_diffrn_reflns_theta_full        29.47
_diffrn_reflns_theta_max         29.47
_diffrn_reflns_theta_min         2.04
_diffrn_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_source_current           43
_diffrn_source_power             2.37
_diffrn_source_voltage           55
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.9679
_exptl_absorpt_correction_T_min  0.9214
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'Stoe X-Red 1.31'
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.057
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepipipede
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.477
_exptl_crystal_size_min          0.320
_refine_diff_density_max         0.712
_refine_diff_density_min         -0.500
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.015(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     297
_refine_ls_number_reflns         7848
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.1030
_refine_ls_R_factor_gt           0.0664
_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^)+(0.1221P)^2^+0.1113P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1966
_refine_ls_wR_factor_ref         0.2171
_reflns_number_gt                4844
_reflns_number_total             7848
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol201745s_si_002.cif
_cod_data_source_block           GLP_399
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1502381