Divergent stereocontrol of acid catalyzed intramolecular aldol reactions of 2,3,7-triketoesters: synthesis of highly functionalized cyclopentanones.
Truong, Phong; Shanahan, Charles S.; Doyle, Michael P.; Organic letters 14 (2012) 3608–3611; doi:10.1021/ol301317a

data_1508286
_publ_section_title
;
 Divergent stereocontrol of acid catalyzed intramolecular aldol reactions
 of 2,3,7-triketoesters: synthesis of highly functionalized
 cyclopentanones.
;
_journal_issue                   14
_journal_name_full               'Organic letters'
_journal_page_first              3608
_journal_page_last               3611
_journal_paper_doi               10.1021/ol301317a
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C14 H16 O5'
_chemical_formula_sum            'C14 H16 O5'
_chemical_formula_weight         264.27
_chemical_name_systematic
;
organic compound
;
_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 & ZCIF'
_cell_angle_alpha                70.3642(7)
_cell_angle_beta                 83.1234(8)
_cell_angle_gamma                71.5902(7)
_cell_formula_units_Z            2
_cell_length_a                   6.5631(4)
_cell_length_b                   9.7944(6)
_cell_length_c                   11.1236(6)
_cell_measurement_reflns_used    5847
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.5
_cell_measurement_theta_min      2.3
_cell_volume                     638.92(7)
_computing_cell_refinement       Apex2
_computing_data_collection       'Apex2 (Bruker, 2005)'
_computing_data_reduction        Apex2
_computing_molecular_graphics    'XSHEL (Bruker, 2004)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 11.198
_diffrn_detector_type            'Bruker Smart Apex II'
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      610,610,610,250
_diffrn_measurement_device_type  'three-circle diffractometer'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_measurement_specimen_support 'MiTeGen loop'
_diffrn_orient_matrix_type       standard
_diffrn_orient_matrix_UB_11      -0.0351070
_diffrn_orient_matrix_UB_12      -0.0868519
_diffrn_orient_matrix_UB_13      0.0681536
_diffrn_orient_matrix_UB_21      -0.0205234
_diffrn_orient_matrix_UB_22      0.0560069
_diffrn_orient_matrix_UB_23      0.0630389
_diffrn_orient_matrix_UB_31      -0.1553711
_diffrn_orient_matrix_UB_32      0.0467853
_diffrn_orient_matrix_UB_33      -0.0222244
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0143
_diffrn_reflns_av_sigmaI/netI    0.0181
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8173
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         1.94
_diffrn_source_current           30.00
_diffrn_source_voltage           50.00
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.964
_exptl_absorpt_correction_T_min  0.903
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             280
_exptl_crystal_id                'Doyle/Truong C14H18O5 150K'
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.435
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3696
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0362
_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^)+(0.005P)^2^+0.3375P], P=(max(Fo^2^,0)+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0707
_refine_ls_wR_factor_ref         0.0716
_reflns_number_gt                3356
_reflns_number_total             3696
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol301317a_si_004.cif
_cod_data_source_block           2128
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 

 Adding full bibliography for 1508285--1508286.cif.
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1508286
_diffrn_measurement_frame_width-ccd -0.30
_diffrn_measurement_total_frames-ccd 2080
_diffrn_measurement_frame_time-ccd 25
_diffrn_measurement_total_time-ccd 17.3
_diffrn_detector_distance-ccd    5.000
_diffrn_measurement_frame_size-ccd 512