Highly enantioselective synthesis of dihydrocoumarin-fused dihydropyrans via the phosphine-catalyzed [4 + 2] annulation of allenones with 3-aroylcoumarins.
Han, Xiaoyu; Ni, Huanzhen; Chan, Wai-Lun; Gai, Xikun; Wang, Yongjiang; Lu, Yixin; Organic & biomolecular chemistry 14 (2016) 5059–5064; doi:10.1039/c6ob00955g

data_7155105
_publ_section_title
;
 Highly enantioselective synthesis of dihydrocoumarin-fused dihydropyrans
 via the phosphine-catalyzed [4 + 2] annulation of allenones with
 3-aroylcoumarins.
;
_journal_issue                   22
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5059
_journal_page_last               5064
_journal_paper_doi               10.1039/c6ob00955g
_journal_volume                  14
_journal_year                    2016
_chemical_absolute_configuration rm
_chemical_compound_source        stable
_chemical_formula_sum            'C27 H20 O4'
_chemical_formula_weight         408.43
_chemical_name_systematic
(R,E)-2-(1-oxo-1-phenylpropan-2-ylidene)-4-phenyl-1,10b-dihydro-2H,5H-pyrano[3,4-c]chromen-5-one
_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
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-02-23 deposited with the CCDC.
2016-05-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.0372(4)
_cell_length_b                   13.0997(5)
_cell_length_c                   15.0079(5)
_cell_measurement_reflns_used    9193
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      70.85
_cell_measurement_theta_min      3.37
_cell_volume                     1973.30(13)
_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-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker D8 venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0555
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            41016
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.914
_diffrn_reflns_theta_min         4.480
_exptl_absorpt_coefficient_mu    0.741
_exptl_absorpt_correction_T_max  0.7534
_exptl_absorpt_correction_T_min  0.5266
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2012)'
_exptl_crystal_colour            'white '
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       Rod
_exptl_crystal_F_000             856
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ethyl acetate, hexane'
_exptl_crystal_size_max          0.510
_exptl_crystal_size_mid          0.209
_exptl_crystal_size_min          0.158
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
; 
 Flack x determined using 1605 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.04(4)
_refine_ls_extinction_coef       0.0032(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         3810
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0305
_refine_ls_R_factor_gt           0.0302
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0525P)^2^+0.3514P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0793
_refine_ls_wR_factor_ref         0.0796
_reflns_Friedel_coverage         0.749
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                3773
_reflns_number_total             3810
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ob00955g2.cif
_cod_data_source_block           F618
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

'_exptl_crystal_density_meas' value 'Not Measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 7155105.cif.
;
_cod_database_code               7155105
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.704
_shelx_estimated_absorpt_t_max   0.892
_shelx_res_checksum              31105