Asymmetric Domino Multicatalysis for the Synthesis of 3-Substituted Phthalides: Cinchonine/NHC Cooperative System.
Youn, So Won; Song, Hyoung Sub; Park, Jong Hyub; Organic letters 16 (2014) 1028–1031; doi:10.1021/ol5000617

data_1513481
_publ_section_title
;
 Asymmetric Domino Multicatalysis for the Synthesis of 3-Substituted
 Phthalides: Cinchonine/NHC Cooperative System.
;
_journal_issue                   3
_journal_name_full               'Organic letters'
_journal_page_first              1028
_journal_page_last               1031
_journal_paper_doi               10.1021/ol5000617
_journal_volume                  16
_journal_year                    2014
_chemical_absolute_configuration unk
_chemical_formula_sum            'C13 H14 O4'
_chemical_formula_weight         234.24
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 110.7080(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   21.8649(16)
_cell_length_b                   13.0933(9)
_cell_length_c                   17.7804(13)
_cell_measurement_reflns_used    5516
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      23.72
_cell_measurement_theta_min      2.55
_cell_volume                     4761.4(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_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  0.0492
_diffrn_reflns_av_sigmaI/netI    0.0746
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            35355
_diffrn_reflns_theta_full        28.37
_diffrn_reflns_theta_max         28.37
_diffrn_reflns_theta_min         1.22
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.9865
_exptl_absorpt_correction_T_min  0.9648
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1984
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.530
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1.1(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     613
_refine_ls_number_reflns         11848
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0915
_refine_ls_R_factor_gt           0.0683
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1079P)^2^+1.2893P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1824
_refine_ls_wR_factor_ref         0.2024
_reflns_number_gt                8678
_reflns_number_total             11848
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5000617_si_002.cif
_cod_data_source_block           me
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_absolute_configuration' value 'UNK' changed to 'unk'
according to
/usr/data/users/saulius/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

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

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' according to
/usr/data/users/saulius/automatic-downloads/current/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      C2
_cod_database_code               1513481