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_1504021
_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            'C24 H30 O3'
_chemical_formula_weight         366.48
_chemical_melting_point          391.0(10)
_chemical_name_systematic
; 
 Methyl (RaSa,10SR,13SR)-13-Hydroxy-13-isopropyl-10,11,12,13,14,15-
 hexahydro-9H-dibenzo[a,c][11]annulene-10-carboxylate 
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 104.415(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.4941(15)
_cell_length_b                   15.472(3)
_cell_length_c                   15.680(3)
_cell_measurement_reflns_used    952
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      30.4
_cell_measurement_theta_min      4.7
_cell_volume                     1995.8(6)
_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      133(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'SMART CCD'
_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  0.0133
_diffrn_reflns_av_sigmaI/netI    0.0137
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            14292
_diffrn_reflns_theta_full        30.52
_diffrn_reflns_theta_max         30.52
_diffrn_reflns_theta_min         2.63
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.8622
_exptl_absorpt_correction_T_min  0.8165
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (BRUKER-AXS)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.5(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         4981
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0323
_refine_ls_R_factor_gt           0.0315
_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^)+(0.0586P)^2^+0.3933P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0838
_refine_ls_wR_factor_ref         0.0846
_reflns_number_gt                4866
_reflns_number_total             4981
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol901183h_si_001.cif
_cod_data_source_block           js290b
_cod_depositor_comments
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The following automatic conversions were performed:

'_chemical_melting_point' value '390-392' was changed to '391.0(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_sg_symbol_H-M      Cc
_cod_database_code               1504021