Unprecedented reactivity pattern of chromium fischer carbene complexes. Direct application to one-pot synthesis of 4-aryl-3,4-dihydrocoumarins on a multigram scale.
Barluenga, José; Andina, Facundo; Aznar, Fernando; Organic letters 8 (2006) 2703–2706; doi:10.1021/ol060702e

data_1505995
_publ_section_title
;
 Unprecedented reactivity pattern of chromium fischer carbene complexes.
 Direct application to one-pot synthesis of 4-aryl-3,4-dihydrocoumarins on
 a multigram scale.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              2703
_journal_page_last               2706
_journal_paper_doi               10.1021/ol060702e
_journal_volume                  8
_journal_year                    2006
_chemical_formula_moiety         'C20 H18 O3 S2'
_chemical_formula_sum            'C20 H18 O3 S2'
_chemical_formula_weight         370.46
_chemical_name_systematic
;
 6-methoxy-3,3-dimethyl-4,8-di(thiophen-2-yl)chroman-2-one
;
_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
_cell_angle_alpha                90.000(2)
_cell_angle_beta                 92.158(2)
_cell_angle_gamma                90.000(2)
_cell_formula_units_Z            4
_cell_length_a                   10.8990(10)
_cell_length_b                   11.0190(10)
_cell_length_c                   15.3570(10)
_cell_measurement_reflns_used    11942
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      56.60
_cell_measurement_theta_min      4.50
_cell_volume                     1843.0(3)
_computing_cell_refinement       'BRUKER SAINT'
_computing_data_collection       'BRUKER SMART'
_computing_data_reduction        'BRUKER SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.952
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0273
_diffrn_reflns_av_sigmaI/netI    0.0395
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11619
_diffrn_reflns_theta_full        28.29
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         2.25
_diffrn_standards_decay_%        1.9
_exptl_absorpt_coefficient_mu    0.304
_exptl_absorpt_correction_T_max  0.9652
_exptl_absorpt_correction_T_min  0.9557
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.838
_refine_diff_density_min         -0.695
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         4370
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.1251
_refine_ls_R_factor_gt           0.0791
_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^)+(0.1612P)^2^+1.2519P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2498
_refine_ls_wR_factor_ref         0.2904
_reflns_number_gt                2549
_reflns_number_total             4370
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol060702esi20060518_071642.cif
_cod_data_source_block           4c
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               1505995