Aluminum Chloride-Mediated Dieckmann Cyclization for the Synthesis of Cyclic 2-Alkyl-1,3-alkanediones: One-Step Synthesis of the Chiloglottones.
Armaly, Ahlam M.; Bar, Sukanta; Schindler, Corinna S.; Organic letters 19 (2017) 3958–3961; doi:10.1021/acs.orglett.7b01622

data_1547121
_publ_section_title
;
 Aluminum Chloride-Mediated Dieckmann Cyclization for the Synthesis of
 Cyclic 2-Alkyl-1,3-alkanediones: One-Step Synthesis of the
 Chiloglottones.
;
_journal_issue                   15
_journal_name_full               'Organic letters'
_journal_page_first              3958
_journal_page_last               3961
_journal_paper_doi               10.1021/acs.orglett.7b01622
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C9 H12 O3'
_chemical_formula_sum            'C9 H12 O3'
_chemical_formula_weight         168.19
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 105.794(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.8820(2)
_cell_length_b                   9.3288(2)
_cell_length_c                   11.9801(8)
_cell_measurement_reflns_used    7874
_cell_measurement_temperature    85(2)
_cell_measurement_theta_max      68.30
_cell_measurement_theta_min      4.70
_cell_volume                     847.64(7)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r16'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r16'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_diffrn_ambient_temperature      85(2)
_diffrn_detector_area_resol_mean 14.629
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Rigaku Saturn944+ CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0572
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12771
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.221
_diffrn_reflns_theta_min         5.834
_diffrn_source                   'micro-focus rotating anode'
_exptl_absorpt_coefficient_mu    0.816
_exptl_absorpt_correction_T_max  0.898
_exptl_absorpt_correction_T_min  0.769
_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    1.318
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       0.038(3)
_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   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     117
_refine_ls_number_reflns         1543
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0417
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0578P)^2^+0.3033P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1023
_refine_ls_wR_factor_ref         0.1034
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1494
_reflns_number_total             1543
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b01622_si_001.cif
_cod_data_source_block           sb379
_cod_database_code               1547121
_shelx_estimated_absorpt_t_min   0.841
_shelx_estimated_absorpt_t_max   0.908
_shelxl_version_number           2014/6
_shelx_res_checksum              28576
_shelx_hkl_checksum              84852