SmI2-promoted Reformatsky-type reaction and acylation of alkyl 1-chlorocyclopropanecarboxylates.
Nagano, Takao; Motoyoshiya, Jiro; Kakehi, Akikazu; Nishii, Yoshinori; Organic letters 10 (2008) 5453–5456; doi:10.1021/ol8022038

data_1504951
_publ_section_title
;
 SmI2-promoted Reformatsky-type reaction and acylation of alkyl
 1-chlorocyclopropanecarboxylates.
;
_journal_issue                   23
_journal_name_full               'Organic letters'
_journal_page_first              5453
_journal_page_last               5456
_journal_paper_doi               10.1021/ol8022038
_journal_volume                  10
_journal_year                    2008
_chemical_formula_moiety         'C18 H26 O3 '
_chemical_formula_sum            'C18 H26 O3'
_chemical_formula_weight         290.40
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_cell_angle_alpha                90.0000
_cell_angle_beta                 94.0063(8)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   8.10238(15)
_cell_length_b                   12.8053(2)
_cell_length_c                   15.8078(7)
_cell_measurement_reflns_used    13917
_cell_measurement_temperature    93.1
_cell_measurement_theta_max      68.2
_cell_measurement_theta_min      5.5
_cell_volume                     1636.11(8)
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku & RAC 2007)'
_computing_molecular_graphics    'ORTEP (Johnson, 1976)'
_computing_publication_material  'CrystalStructure (Rigaku & RAC 2007)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.020
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            18272
_diffrn_reflns_theta_full        68.19
_diffrn_reflns_theta_max         68.19
_exptl_absorpt_coefficient_mu    0.624
_exptl_absorpt_correction_T_max  0.940
_exptl_absorpt_correction_T_min  0.888
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;

    Higashi, T. (1995). Program for Absorption Correction.

    Rigaku Corporation, Tokyo, Japan.

;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.179
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             632.00
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.30
_refine_diff_density_min         -0.21
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     197
_refine_ls_number_reflns         2976
_refine_ls_R_factor_gt           0.0359
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0395P)^2^+0.6655P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0902
_reflns_number_gt                2708
_reflns_number_total             2976
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ol8022038_si_004.cif
_cod_data_source_block           '_Nishii-Lab'
_cod_original_formula_sum        'C18 H26 O3 '
_cod_database_code               1504951