Medium-sized carbocycles by samarium diiodide-induced carbonyl-alkene cyclizations.
Saadi, Jakub; Lentz, Dieter; Reissig, Hans-Ulrich; Organic letters 11 (2009) 3334–3337; doi:10.1021/ol901183h

data_1504020
_publ_section_title
;
 Medium-sized carbocycles by samarium diiodide-induced carbonyl-alkene
 cyclizations.
;
_journal_issue                   15
_journal_name_full               'Organic letters'
_journal_page_first              3334
_journal_page_last               3337
_journal_paper_doi               10.1021/ol901183h
_journal_volume                  11
_journal_year                    2009
_chemical_formula_sum            'C23 H28 O'
_chemical_formula_weight         320.45
_chemical_melting_point          374.0(10)
_chemical_name_systematic
; 
 (3SR,3aRS,4SR,9aRS)-4-Benzyl-3-isopropyl-1,2,3,4,9,9a-hexahydro-
  3aH-cyclopenta[b]naphthalen-3a-ol 
;
_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_method           SHELXL-97
_cell_angle_alpha                71.800(5)
_cell_angle_beta                 88.188(4)
_cell_angle_gamma                70.926(4)
_cell_formula_units_Z            4
_cell_length_a                   9.769(2)
_cell_length_b                   14.360(3)
_cell_length_c                   14.469(3)
_cell_measurement_reflns_used    989
_cell_measurement_temperature    143(2)
_cell_measurement_theta_max      30.4
_cell_measurement_theta_min      2.5
_cell_volume                     1816.7(7)
_computing_cell_refinement       'SAINT (BRUKER-AXS)'
_computing_data_collection       'SMART (Bruker-AXS)'
_computing_data_reduction        'SAINT (BRUKER-AXS)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      143(2)
_diffrn_measured_fraction_theta_full 0.951
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_device_type  'SMART CCD Bruker-AXS'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0593
_diffrn_reflns_av_sigmaI/netI    0.0558
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14158
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         1.58
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.172
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.560
_refine_diff_density_min         -0.428
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     439
_refine_ls_number_reflns         8558
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0602
_refine_ls_R_factor_gt           0.0476
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0658P)^2^+0.3899P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1248
_refine_ls_wR_factor_ref         0.1346
_reflns_number_gt                6794
_reflns_number_total             8558
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol901183h_si_001.cif
_cod_data_source_block           js269c
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '373-375' was changed to '374.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1816.7(6)
_cod_original_sg_symbol_H-M      P-1
_cod_original_formula_sum        'C23 H28 O1'
_cod_database_code               1504020