Enantioselective formation of substituted 3,4-dihydrocoumarins by a multicatalytic one-pot process.
Jacobsen, Christian Borch; Albrecht, Łukasz; Udmark, Jonas; Jørgensen, Karl Anker; Organic letters 14 (2012) 5526–5529; doi:10.1021/ol302627u

data_1508740
_publ_section_title
;
 Enantioselective formation of substituted 3,4-dihydrocoumarins by a
 multicatalytic one-pot process.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              5526
_journal_page_last               5529
_journal_paper_doi               10.1021/ol302627u
_journal_volume                  14
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H13 Br O3'
_chemical_formula_sum            'C17 H13 Br O3'
_chemical_formula_weight         345.18
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2012-08-23
_audit_creation_method
;
  Olex2 1.2
  (compiled 2012.05.09 svn.r2324, GUI svn.r4230)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.7141(10)
_cell_length_b                   13.121(2)
_cell_length_c                   18.590(3)
_cell_measurement_reflns_used    9975
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.56
_cell_measurement_theta_min      2.69
_cell_volume                     1393.8(4)
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.899
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_av_unetI/netI     0.0169
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            42569
_diffrn_reflns_theta_full        29.50
_diffrn_reflns_theta_max         31.55
_diffrn_reflns_theta_min         1.90
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.956
_exptl_absorpt_correction_T_max  0.7145
_exptl_absorpt_correction_T_min  0.4232
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0957 before and 0.0494 after correction.
The Ratio of minimum to maximum transmission is 0.5923.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.645
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.277
_exptl_crystal_size_min          0.107
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.003(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         4004
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0172
_refine_ls_R_factor_gt           0.0165
_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^)+(0.0196P)^2^+0.3586P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0401
_refine_ls_wR_factor_ref         0.0403
_reflns_number_gt                3920
_reflns_number_total             4004
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol302627u_si_002.cif
_cod_data_source_block           12jo0010a_0m
_cod_original_cell_volume        1393.7(4)
_cod_database_code               1508740