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_1516101
_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         'C20 H18 O5'
_chemical_formula_sum            'C20 H18 O5'
_chemical_formula_weight         338.34
_chemical_name_common            diphenyl
_chemical_name_systematic
;
diphenyl
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                90.00
_cell_angle_beta                 106.5495(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.4332(15)
_cell_length_b                   5.5136(5)
_cell_length_c                   18.3321(17)
_cell_measurement_reflns_used    11898
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.0
_cell_measurement_theta_min      2.3
_cell_volume                     1592.2(3)
_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      100(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 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
; Measured frames                     366,366,366,720
_diffrn_measurement_frame_width-CCD  -0.5
_diffrn_measurement_total_frames-CCD  1818
_diffrn_measurement_frame_time-CCD    15
_diffrn_measurement_total_time-CCD    10.6
_diffrn_detector_distance-CCD         5.00
_diffrn_measurement_frame_size-CCD    512
;
_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      -0.0334461
_diffrn_orient_matrix_UB_12      -0.0362244
_diffrn_orient_matrix_UB_13      0.0364733
_diffrn_orient_matrix_UB_21      -0.0533474
_diffrn_orient_matrix_UB_22      0.0481672
_diffrn_orient_matrix_UB_23      -0.0393272
_diffrn_orient_matrix_UB_31      -0.0079283
_diffrn_orient_matrix_UB_32      -0.1710394
_diffrn_orient_matrix_UB_33      -0.0189603
_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  0.0309
_diffrn_reflns_av_sigmaI/netI    0.0250
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            23378
_diffrn_reflns_theta_full        29.99
_diffrn_reflns_theta_max         29.99
_diffrn_reflns_theta_min         1.97
_diffrn_source_current           30.00
_diffrn_source_voltage           50.00
_diffrn_standards_interval_count '$REMOVE_ENTRY'
_diffrn_standards_interval_time  '$REMOVE_ENTRY'
_diffrn_standards_number         '$REMOVE_ENTRY'
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.928
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.418
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.047
_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     295
_refine_ls_number_reflns         4642
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0368
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.01P)^2^+1.146P], P=(max(Fo^2^,0)+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0762
_refine_ls_wR_factor_ref         0.0778
_reflns_number_gt                4093
_reflns_number_total             4642
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol301317a_si_003.cif
_cod_data_source_block           2041
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/retrospective/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1516101