Asymmetric Synthesis of All-Carbon Benzylic Quaternary Stereocenters via Conjugate Addition to Alkylidene and Indenylidene Meldrum's Acids
Ashraf Wilsily; Eric Fillion; Journal of Organic Chemistry 74 (2009) 8583–8594; doi:10.1021/jo901559d

data_4025027
_publ_section_title
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Asymmetric Synthesis of All-Carbon Benzylic Quaternary Stereocenters via
Conjugate Addition to Alkylidene and Indenylidene Meldrum's Acids
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_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8583
_journal_page_last               8594
_journal_paper_doi               10.1021/jo901559d
_journal_volume                  74
_journal_year                    2009
_chemical_formula_sum            'C14 H13 Cl O4'
_chemical_formula_weight         280.69
_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
_cell_angle_alpha                81.573(1)
_cell_angle_beta                 74.927(1)
_cell_angle_gamma                86.963(1)
_cell_formula_units_Z            2
_cell_length_a                   6.9919(3)
_cell_length_b                   7.4350(3)
_cell_length_c                   13.1352(5)
_cell_measurement_reflns_used    7541
_cell_measurement_temperature    180(1)
_cell_measurement_theta_max      34.99
_cell_measurement_theta_min      2.77
_cell_volume                     652.14(5)
_computing_cell_refinement       SAINT
_computing_data_collection       SMART
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    SHELXTL
_diffrn_ambient_temperature      180(1)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX'
_diffrn_measurement_method       Omega
_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  0.0262
_diffrn_reflns_av_sigmaI/netI    0.0256
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7207
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         1.62
_exptl_absorpt_coefficient_mu    0.300
_exptl_absorpt_correction_T_max  0.948
_exptl_absorpt_correction_T_min  0.910
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'Face-indexed analytical'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'Needle plate fragment'
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.406
_refine_diff_density_min         -0.409
_refine_diff_density_rms         0.063
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_goodness_of_fit_ref   2.257
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         3229
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      2.257
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0406
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0300P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1140
_refine_ls_wR_factor_ref         0.1148
_reflns_number_gt                2949
_reflns_number_total             3229
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo901559d_si_004.cif
_cod_data_source_block           ef1269m
_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 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Integration' changed
to 'integration' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4025027